 
data_np8 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C24 H19 N O' 
_chemical_formula_weight          337.40 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    12.5295(10) 
_cell_length_b                    6.1140(4) 
_cell_length_c                    24.4215(18) 
_cell_angle_alpha                 90 
_cell_angle_beta                  104.339(3) 
_cell_angle_gamma                 90 
_cell_volume                      1812.5(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     2037 
_cell_measurement_theta_min       2.69 
_cell_measurement_theta_max       21.36 
  
_exptl_crystal_description        Rectangular 
_exptl_crystal_colour             red 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.236 
_exptl_crystal_F_000              712 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.250 
_exptl_crystal_size_mid           0.160 
_exptl_crystal_size_min           0.120 
_exptl_absorpt_coefficient_mu     0.075 
_shelx_estimated_absorpt_T_min    0.981 
_shelx_estimated_absorpt_T_max    0.991 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.981 
_exptl_absorpt_correction_T_max   0.991 
_exptl_absorpt_process_details     'SADABS V2014/5(Bruker AXS.Inc)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             11768 
_diffrn_reflns_av_unetI/netI      0.0493 
_diffrn_reflns_av_R_equivalents   0.0433 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -7 
_diffrn_reflns_limit_k_max        5 
_diffrn_reflns_limit_l_min        -29 
_diffrn_reflns_limit_l_max        29 
_diffrn_reflns_theta_min          2.085 
_diffrn_reflns_theta_max          25.000 
_diffrn_reflns_theta_full         25.000 
_diffrn_measured_fraction_theta_max   0.999 
_diffrn_measured_fraction_theta_full  0.999 
_diffrn_reflns_Laue_measured_fraction_max    0.999 
_diffrn_reflns_Laue_measured_fraction_full   0.999 
_diffrn_reflns_point_group_measured_fraction_max   0.999 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
_reflns_number_total              3195 
_reflns_number_gt                 1938 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0572P)²] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014' 
_refine_ls_extinction_coef        0.0064(11) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3195 
_refine_ls_number_parameters      237 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0891 
_refine_ls_R_factor_gt            0.0433 
_refine_ls_wR_factor_ref          0.1191 
_refine_ls_wR_factor_gt           0.0976 
_refine_ls_goodness_of_fit_ref    1.005 
_refine_ls_restrained_S_all       1.005 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C -0.02181(18) -0.3125(3) 0.15752(9) 0.0592(6) Uani 1 1 d . . . . . 
H1 H -0.0021 -0.1854 0.1785 0.071 Uiso 1 1 calc R U . . . 
C2 C -0.09512(19) -0.4558(4) 0.17197(9) 0.0722(7) Uani 1 1 d . . . . . 
H2 H -0.1244 -0.4254 0.2026 0.087 Uiso 1 1 calc R U . . . 
C3 C -0.1251(2) -0.6447(4) 0.14099(10) 0.0742(7) Uani 1 1 d . . . . . 
H3 H -0.1744 -0.7417 0.1508 0.089 Uiso 1 1 calc R U . . . 
C4 C -0.08220(19) -0.6896(3) 0.09572(10) 0.0656(6) Uani 1 1 d . . . . . 
H4 H -0.1025 -0.8166 0.0748 0.079 Uiso 1 1 calc R U . . . 
C5 C -0.00923(17) -0.5462(3) 0.08145(8) 0.0523(6) Uani 1 1 d . . . . . 
H5 H 0.0192 -0.5776 0.0506 0.063 Uiso 1 1 calc R U . . . 
C6 C 0.02314(16) -0.3555(3) 0.11192(7) 0.0450(5) Uani 1 1 d . . . . . 
C7 C 0.10386(16) -0.2132(3) 0.09585(8) 0.0472(5) Uani 1 1 d . . . . . 
H7 H 0.1219 -0.2445 0.0620 0.057 Uiso 1 1 calc R U . . . 
C8 C 0.15423(16) -0.0420(3) 0.12538(8) 0.0462(5) Uani 1 1 d . . . . . 
H8 H 0.1323 -0.0040 0.1578 0.055 Uiso 1 1 calc R U . . . 
C9 C 0.23944(16) 0.0886(3) 0.11140(7) 0.0403(5) Uani 1 1 d . . . . . 
C10 C 0.29198(16) 0.2525(3) 0.14581(7) 0.0414(5) Uani 1 1 d . . . . . 
C11 C 0.38847(16) 0.3808(3) 0.14203(7) 0.0403(5) Uani 1 1 d . . . . . 
C12 C 0.46578(16) 0.3633(3) 0.11029(8) 0.0462(5) Uani 1 1 d . . . . . 
H12 H 0.4583 0.2562 0.0826 0.055 Uiso 1 1 calc R U . . . 
C13 C 0.55410(18) 0.5064(3) 0.12013(8) 0.0548(6) Uani 1 1 d . . . . . 
H13 H 0.6062 0.4942 0.0990 0.066 Uiso 1 1 calc R U . . . 
C14 C 0.5657(2) 0.6669(3) 0.16087(9) 0.0628(6) Uani 1 1 d . . . . . 
H14 H 0.6253 0.7623 0.1667 0.075 Uiso 1 1 calc R U . . . 
C15 C 0.4901(2) 0.6877(3) 0.19312(8) 0.0607(6) Uani 1 1 d . . . . . 
H15 H 0.4977 0.7961 0.2205 0.073 Uiso 1 1 calc R U . . . 
C16 C 0.40316(17) 0.5437(3) 0.18368(7) 0.0452(5) Uani 1 1 d . . . . . 
C17 C 0.25582(18) 0.3434(3) 0.19542(8) 0.0471(5) Uani 1 1 d . . . . . 
C18 C 0.27027(15) 0.0471(3) 0.05701(7) 0.0386(5) Uani 1 1 d . . . . . 
C19 C 0.33060(16) -0.1338(3) 0.04873(8) 0.0474(5) Uani 1 1 d . . . . . 
H19 H 0.3490 -0.2398 0.0768 0.057 Uiso 1 1 calc R U . . . 
C20 C 0.36366(18) -0.1588(3) -0.00040(8) 0.0569(6) Uani 1 1 d . . . . . 
H20 H 0.4055 -0.2799 -0.0050 0.068 Uiso 1 1 calc R U . . . 
C21 C 0.33553(18) -0.0070(3) -0.04280(8) 0.0587(6) Uani 1 1 d . . . . . 
H21 H 0.3585 -0.0245 -0.0760 0.070 Uiso 1 1 calc R U . . . 
C22 C 0.27328(17) 0.1710(3) -0.03603(8) 0.0557(6) Uani 1 1 d . . . . . 
H22 H 0.2528 0.2732 -0.0649 0.067 Uiso 1 1 calc R U . . . 
C23 C 0.24126(16) 0.1984(3) 0.01350(8) 0.0481(5) Uani 1 1 d . . . . . 
H23 H 0.1996 0.3200 0.0179 0.058 Uiso 1 1 calc R U . . . 
C24 C 0.3063(2) 0.6701(3) 0.25732(8) 0.0713(7) Uani 1 1 d . . . . . 
H24A H 0.2423 0.6264 0.2695 0.107 Uiso 1 1 calc R U . . . 
H24B H 0.2968 0.8172 0.2432 0.107 Uiso 1 1 calc R U . . . 
H24C H 0.3700 0.6632 0.2887 0.107 Uiso 1 1 calc R U . . . 
N1 N 0.32127(14) 0.5244(2) 0.21294(6) 0.0500(5) Uani 1 1 d . . . . . 
O1 O 0.18440(13) 0.2820(2) 0.21777(6) 0.0643(4) Uani 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 C2 1.377(3) . ? 
C1 C6 1.392(3) . ? 
C1 H1 0.9300 . ? 
C2 C3 1.381(3) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.371(3) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.372(3) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.389(2) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.460(2) . ? 
C7 C8 1.337(2) . ? 
C7 H7 0.9300 . ? 
C8 C9 1.440(3) . ? 
C8 H8 0.9300 . ? 
C9 C10 1.367(2) . ? 
C9 C18 1.494(2) . ? 
C10 C11 1.463(3) . ? 
C10 C17 1.501(2) . ? 
C11 C12 1.386(2) . ? 
C11 C16 1.403(2) . ? 
C12 C13 1.384(3) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.379(3) . ? 
C13 H13 0.9300 . ? 
C14 C15 1.380(3) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.375(3) . ? 
C15 H15 0.9300 . ? 
C16 N1 1.393(2) . ? 
C17 O1 1.217(2) . ? 
C17 N1 1.381(2) . ? 
C18 C19 1.383(2) . ? 
C18 C23 1.387(2) . ? 
C19 C20 1.371(2) . ? 
C19 H19 0.9300 . ? 
C20 C21 1.370(3) . ? 
C20 H20 0.9300 . ? 
C21 C22 1.373(3) . ? 
C21 H21 0.9300 . ? 
C22 C23 1.376(2) . ? 
C22 H22 0.9300 . ? 
C23 H23 0.9300 . ? 
C24 N1 1.451(2) . ? 
C24 H24A 0.9600 . ? 
C24 H24B 0.9600 . ? 
C24 H24C 0.9600 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 C6 120.8(2) . . ? 
C2 C1 H1 119.6 . . ? 
C6 C1 H1 119.6 . . ? 
C1 C2 C3 120.0(2) . . ? 
C1 C2 H2 120.0 . . ? 
C3 C2 H2 120.0 . . ? 
C4 C3 C2 120.1(2) . . ? 
C4 C3 H3 120.0 . . ? 
C2 C3 H3 120.0 . . ? 
C3 C4 C5 119.7(2) . . ? 
C3 C4 H4 120.1 . . ? 
C5 C4 H4 120.1 . . ? 
C4 C5 C6 121.65(19) . . ? 
C4 C5 H5 119.2 . . ? 
C6 C5 H5 119.2 . . ? 
C5 C6 C1 117.71(17) . . ? 
C5 C6 C7 119.10(17) . . ? 
C1 C6 C7 123.17(17) . . ? 
C8 C7 C6 125.97(18) . . ? 
C8 C7 H7 117.0 . . ? 
C6 C7 H7 117.0 . . ? 
C7 C8 C9 125.77(17) . . ? 
C7 C8 H8 117.1 . . ? 
C9 C8 H8 117.1 . . ? 
C10 C9 C8 122.20(16) . . ? 
C10 C9 C18 118.65(16) . . ? 
C8 C9 C18 119.13(15) . . ? 
C9 C10 C11 129.33(16) . . ? 
C9 C10 C17 124.87(17) . . ? 
C11 C10 C17 105.75(15) . . ? 
C12 C11 C16 118.40(18) . . ? 
C12 C11 C10 134.15(16) . . ? 
C16 C11 C10 107.28(17) . . ? 
C13 C12 C11 119.57(18) . . ? 
C13 C12 H12 120.2 . . ? 
C11 C12 H12 120.2 . . ? 
C14 C13 C12 120.8(2) . . ? 
C14 C13 H13 119.6 . . ? 
C12 C13 H13 119.6 . . ? 
C13 C14 C15 120.8(2) . . ? 
C13 C14 H14 119.6 . . ? 
C15 C14 H14 119.6 . . ? 
C16 C15 C14 118.22(19) . . ? 
C16 C15 H15 120.9 . . ? 
C14 C15 H15 120.9 . . ? 
C15 C16 N1 128.44(18) . . ? 
C15 C16 C11 122.2(2) . . ? 
N1 C16 C11 109.32(17) . . ? 
O1 C17 N1 123.70(18) . . ? 
O1 C17 C10 130.51(18) . . ? 
N1 C17 C10 105.79(17) . . ? 
C19 C18 C23 118.06(17) . . ? 
C19 C18 C9 122.46(15) . . ? 
C23 C18 C9 119.44(16) . . ? 
C20 C19 C18 120.77(17) . . ? 
C20 C19 H19 119.6 . . ? 
C18 C19 H19 119.6 . . ? 
C21 C20 C19 120.58(18) . . ? 
C21 C20 H20 119.7 . . ? 
C19 C20 H20 119.7 . . ? 
C20 C21 C22 119.59(19) . . ? 
C20 C21 H21 120.2 . . ? 
C22 C21 H21 120.2 . . ? 
C21 C22 C23 120.03(18) . . ? 
C21 C22 H22 120.0 . . ? 
C23 C22 H22 120.0 . . ? 
C22 C23 C18 120.94(17) . . ? 
C22 C23 H23 119.5 . . ? 
C18 C23 H23 119.5 . . ? 
N1 C24 H24A 109.5 . . ? 
N1 C24 H24B 109.5 . . ? 
H24A C24 H24B 109.5 . . ? 
N1 C24 H24C 109.5 . . ? 
H24A C24 H24C 109.5 . . ? 
H24B C24 H24C 109.5 . . ? 
C17 N1 C16 111.42(15) . . ? 
C17 N1 C24 123.16(18) . . ? 
C16 N1 C24 125.40(17) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C6 C1 C2 C3 -0.2(3) . . . . ? 
C1 C2 C3 C4 -0.2(4) . . . . ? 
C2 C3 C4 C5 0.1(4) . . . . ? 
C3 C4 C5 C6 0.3(3) . . . . ? 
C4 C5 C6 C1 -0.6(3) . . . . ? 
C4 C5 C6 C7 177.94(18) . . . . ? 
C2 C1 C6 C5 0.5(3) . . . . ? 
C2 C1 C6 C7 -177.93(19) . . . . ? 
C5 C6 C7 C8 -170.13(18) . . . . ? 
C1 C6 C7 C8 8.3(3) . . . . ? 
C6 C7 C8 C9 175.36(17) . . . . ? 
C7 C8 C9 C10 -175.63(18) . . . . ? 
C7 C8 C9 C18 5.6(3) . . . . ? 
C8 C9 C10 C11 171.30(17) . . . . ? 
C18 C9 C10 C11 -9.9(3) . . . . ? 
C8 C9 C10 C17 -11.5(3) . . . . ? 
C18 C9 C10 C17 167.26(16) . . . . ? 
C9 C10 C11 C12 -11.0(3) . . . . ? 
C17 C10 C11 C12 171.37(19) . . . . ? 
C9 C10 C11 C16 173.91(18) . . . . ? 
C17 C10 C11 C16 -3.67(18) . . . . ? 
C16 C11 C12 C13 -0.4(3) . . . . ? 
C10 C11 C12 C13 -175.05(18) . . . . ? 
C11 C12 C13 C14 -0.4(3) . . . . ? 
C12 C13 C14 C15 0.5(3) . . . . ? 
C13 C14 C15 C16 0.2(3) . . . . ? 
C14 C15 C16 N1 175.73(18) . . . . ? 
C14 C15 C16 C11 -1.1(3) . . . . ? 
C12 C11 C16 C15 1.2(3) . . . . ? 
C10 C11 C16 C15 177.17(16) . . . . ? 
C12 C11 C16 N1 -176.16(15) . . . . ? 
C10 C11 C16 N1 -0.20(19) . . . . ? 
C9 C10 C17 O1 7.9(3) . . . . ? 
C11 C10 C17 O1 -174.3(2) . . . . ? 
C9 C10 C17 N1 -171.52(16) . . . . ? 
C11 C10 C17 N1 6.21(18) . . . . ? 
C10 C9 C18 C19 107.4(2) . . . . ? 
C8 C9 C18 C19 -73.8(2) . . . . ? 
C10 C9 C18 C23 -70.2(2) . . . . ? 
C8 C9 C18 C23 108.61(19) . . . . ? 
C23 C18 C19 C20 2.1(3) . . . . ? 
C9 C18 C19 C20 -175.59(18) . . . . ? 
C18 C19 C20 C21 -1.4(3) . . . . ? 
C19 C20 C21 C22 -0.3(3) . . . . ? 
C20 C21 C22 C23 1.2(3) . . . . ? 
C21 C22 C23 C18 -0.5(3) . . . . ? 
C19 C18 C23 C22 -1.1(3) . . . . ? 
C9 C18 C23 C22 176.59(17) . . . . ? 
O1 C17 N1 C16 173.88(18) . . . . ? 
C10 C17 N1 C16 -6.62(19) . . . . ? 
O1 C17 N1 C24 -4.7(3) . . . . ? 
C10 C17 N1 C24 174.80(16) . . . . ? 
C15 C16 N1 C17 -172.68(18) . . . . ? 
C11 C16 N1 C17 4.5(2) . . . . ? 
C15 C16 N1 C24 5.9(3) . . . . ? 
C11 C16 N1 C24 -176.98(16) . . . . ? 
  
_refine_diff_density_max    0.131 
_refine_diff_density_min   -0.131 
_refine_diff_density_rms    0.032 
  
  
  
 
data_8 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C21 H19 N O3'  
_chemical_formula_sum 
 'C21 H19 N O3' 
_chemical_formula_weight          333.37 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            15 
_space_group_name_H-M_alt         'C 2/c' 
_space_group_name_Hall            '-C 2yc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y, -z+1/2' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
  
_cell_length_a                    20.5819(9) 
_cell_length_b                    12.8776(5) 
_cell_length_c                    13.9465(6) 
_cell_angle_alpha                 90 
_cell_angle_beta                  102.5359(17) 
_cell_angle_gamma                 90 
_cell_volume                      3608.3(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     3115 
_cell_measurement_theta_min       2.53 
_cell_measurement_theta_max       24.29 
  
_exptl_crystal_description        Block 
_exptl_crystal_colour             brown 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.227 
_exptl_crystal_F_000              1408 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.280 
_exptl_crystal_size_mid           0.220 
_exptl_crystal_size_min           0.160 
_exptl_absorpt_coefficient_mu     0.082 
_shelx_estimated_absorpt_T_min    0.977 
_shelx_estimated_absorpt_T_max    0.987 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.977 
_exptl_absorpt_correction_T_max   0.987 
_exptl_absorpt_process_details     'SADABS V2014/5(Bruker AXS.Inc)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             10809 
_diffrn_reflns_av_unetI/netI      0.0325 
_diffrn_reflns_av_R_equivalents   0.0307 
_diffrn_reflns_limit_h_min        -24 
_diffrn_reflns_limit_h_max        24 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          1.878 
_diffrn_reflns_theta_max          24.997 
_diffrn_reflns_theta_full         24.997 
_diffrn_measured_fraction_theta_max   1.000 
_diffrn_measured_fraction_theta_full  1.000 
_diffrn_reflns_Laue_measured_fraction_max    1.000 
_diffrn_reflns_Laue_measured_fraction_full   1.000 
_diffrn_reflns_point_group_measured_fraction_max   1.000 
_diffrn_reflns_point_group_measured_fraction_full  1.000 
_reflns_number_total              3187 
_reflns_number_gt                 2115 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0710P)²+0.8493P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014' 
_refine_ls_extinction_coef        0.0014(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3187 
_refine_ls_number_parameters      229 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0757 
_refine_ls_R_factor_gt            0.0464 
_refine_ls_wR_factor_ref          0.1414 
_refine_ls_wR_factor_gt           0.1206 
_refine_ls_goodness_of_fit_ref    1.030 
_refine_ls_restrained_S_all       1.030 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.84660(9) -0.18918(16) 0.09485(15) 0.0552(6) Uani 1 1 d . . . . . 
H1 H 0.8134 -0.1391 0.0878 0.066 Uiso 1 1 calc R U . . . 
C2 C 0.83055(11) -0.29397(18) 0.09261(17) 0.0673(6) Uani 1 1 d . . . . . 
H2 H 0.7863 -0.3141 0.0841 0.081 Uiso 1 1 calc R U . . . 
C3 C 0.87952(13) -0.36823(18) 0.10288(17) 0.0717(7) Uani 1 1 d . . . . . 
H3 H 0.8676 -0.4380 0.1007 0.086 Uiso 1 1 calc R U . . . 
C4 C 0.94597(12) -0.34200(16) 0.11641(17) 0.0634(6) Uani 1 1 d . . . . . 
H4 H 0.9790 -0.3926 0.1240 0.076 Uiso 1 1 calc R U . . . 
C5 C 0.96130(10) -0.23807(15) 0.11813(14) 0.0480(5) Uani 1 1 d . . . . . 
C6 C 1.02056(9) -0.08712(16) 0.12976(13) 0.0445(5) Uani 1 1 d . . . . . 
C7 C 0.94751(8) -0.05985(14) 0.11441(13) 0.0403(5) Uani 1 1 d . . . . . 
C8 C 0.91271(9) -0.16017(15) 0.10766(13) 0.0436(5) Uani 1 1 d . . . . . 
C9 C 0.92302(8) 0.03769(14) 0.10920(13) 0.0415(5) Uani 1 1 d . . . . . 
C10 C 0.96551(9) 0.12925(15) 0.12038(14) 0.0467(5) Uani 1 1 d . . . . . 
H10 H 1.0113 0.1193 0.1333 0.056 Uiso 1 1 calc R U . . . 
C11 C 0.94279(10) 0.22604(16) 0.11317(15) 0.0538(5) Uani 1 1 d . . . . . 
H11 H 0.8969 0.2354 0.1014 0.065 Uiso 1 1 calc R U . . . 
C12 C 0.98445(12) 0.31902(18) 0.12238(17) 0.0624(6) Uani 1 1 d . . . . . 
C13 C 1.09497(14) 0.3850(2) 0.1591(2) 0.0852(8) Uani 1 1 d . . . . . 
H13A H 1.0883 0.4309 0.2113 0.102 Uiso 1 1 calc R U . . . 
H13B H 1.0880 0.4244 0.0984 0.102 Uiso 1 1 calc R U . . . 
C14 C 1.16337(14) 0.3409(3) 0.1827(2) 0.1128(11) Uani 1 1 d . . . . . 
H14A H 1.1706 0.3059 0.2449 0.169 Uiso 1 1 calc R U . . . 
H14B H 1.1953 0.3959 0.1859 0.169 Uiso 1 1 calc R U . . . 
H14C H 1.1684 0.2924 0.1325 0.169 Uiso 1 1 calc R U . . . 
C15 C 1.08641(10) -0.24993(19) 0.14451(16) 0.0665(6) Uani 1 1 d . . . . . 
H15A H 1.1229 -0.2019 0.1533 0.100 Uiso 1 1 calc R U . . . 
H15B H 1.0861 -0.2919 0.0875 0.100 Uiso 1 1 calc R U . . . 
H15C H 1.0914 -0.2937 0.2013 0.100 Uiso 1 1 calc R U . . . 
C16 C 0.84979(9) 0.05644(14) 0.09007(15) 0.0445(5) Uani 1 1 d . . . . . 
C17 C 0.81296(9) 0.05851(17) -0.00553(16) 0.0577(6) Uani 1 1 d . . . . . 
H17 H 0.8337 0.0462 -0.0574 0.069 Uiso 1 1 calc R U . . . 
C18 C 0.74554(10) 0.07877(19) -0.0243(2) 0.0724(7) Uani 1 1 d . . . . . 
H18 H 0.7211 0.0799 -0.0888 0.087 Uiso 1 1 calc R U . . . 
C19 C 0.71470(11) 0.0970(2) 0.0504(2) 0.0796(8) Uani 1 1 d . . . . . 
H19 H 0.6692 0.1102 0.0371 0.095 Uiso 1 1 calc R U . . . 
C20 C 0.75024(12) 0.0963(2) 0.1452(2) 0.0808(8) Uani 1 1 d . . . . . 
H20 H 0.7289 0.1091 0.1963 0.097 Uiso 1 1 calc R U . . . 
C21 C 0.81813(10) 0.07638(18) 0.16567(17) 0.0630(6) Uani 1 1 d . . . . . 
H21 H 0.8422 0.0765 0.2303 0.076 Uiso 1 1 calc R U . . . 
N1 N 1.02437(8) -0.19301(13) 0.13150(11) 0.0501(4) Uani 1 1 d . . . . . 
O1 O 1.06894(6) -0.02994(12) 0.13908(10) 0.0594(4) Uani 1 1 d . . . . . 
O2 O 0.96251(10) 0.40507(13) 0.10683(16) 0.1019(7) Uani 1 1 d . . . . . 
O3 O 1.04913(8) 0.29854(12) 0.14889(11) 0.0706(5) Uani 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 C8 1.385(3) . ? 
C1 C2 1.388(3) . ? 
C1 H1 0.9300 . ? 
C2 C3 1.374(3) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.381(3) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.374(3) . ? 
C4 H4 0.9300 . ? 
C5 N1 1.397(2) . ? 
C5 C8 1.402(3) . ? 
C6 O1 1.223(2) . ? 
C6 N1 1.366(3) . ? 
C6 C7 1.513(2) . ? 
C7 C9 1.350(2) . ? 
C7 C8 1.470(3) . ? 
C9 C10 1.456(3) . ? 
C9 C16 1.492(2) . ? 
C10 C11 1.327(3) . ? 
C10 H10 0.9300 . ? 
C11 C12 1.462(3) . ? 
C11 H11 0.9300 . ? 
C12 O2 1.199(3) . ? 
C12 O3 1.329(3) . ? 
C13 O3 1.446(3) . ? 
C13 C14 1.487(4) . ? 
C13 H13A 0.9700 . ? 
C13 H13B 0.9700 . ? 
C14 H14A 0.9600 . ? 
C14 H14B 0.9600 . ? 
C14 H14C 0.9600 . ? 
C15 N1 1.449(2) . ? 
C15 H15A 0.9600 . ? 
C15 H15B 0.9600 . ? 
C15 H15C 0.9600 . ? 
C16 C21 1.379(3) . ? 
C16 C17 1.383(3) . ? 
C17 C18 1.380(3) . ? 
C17 H17 0.9300 . ? 
C18 C19 1.353(3) . ? 
C18 H18 0.9300 . ? 
C19 C20 1.365(4) . ? 
C19 H19 0.9300 . ? 
C20 C21 1.388(3) . ? 
C20 H20 0.9300 . ? 
C21 H21 0.9300 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C8 C1 C2 119.19(19) . . ? 
C8 C1 H1 120.4 . . ? 
C2 C1 H1 120.4 . . ? 
C3 C2 C1 120.6(2) . . ? 
C3 C2 H2 119.7 . . ? 
C1 C2 H2 119.7 . . ? 
C2 C3 C4 121.7(2) . . ? 
C2 C3 H3 119.1 . . ? 
C4 C3 H3 119.1 . . ? 
C5 C4 C3 117.2(2) . . ? 
C5 C4 H4 121.4 . . ? 
C3 C4 H4 121.4 . . ? 
C4 C5 N1 127.60(18) . . ? 
C4 C5 C8 122.64(19) . . ? 
N1 C5 C8 109.75(17) . . ? 
O1 C6 N1 123.85(17) . . ? 
O1 C6 C7 129.54(18) . . ? 
N1 C6 C7 106.60(16) . . ? 
C9 C7 C8 130.04(16) . . ? 
C9 C7 C6 124.86(17) . . ? 
C8 C7 C6 105.10(15) . . ? 
C1 C8 C5 118.64(18) . . ? 
C1 C8 C7 134.17(17) . . ? 
C5 C8 C7 107.19(16) . . ? 
C7 C9 C10 122.63(16) . . ? 
C7 C9 C16 120.74(16) . . ? 
C10 C9 C16 116.62(16) . . ? 
C11 C10 C9 123.97(18) . . ? 
C11 C10 H10 118.0 . . ? 
C9 C10 H10 118.0 . . ? 
C10 C11 C12 124.9(2) . . ? 
C10 C11 H11 117.6 . . ? 
C12 C11 H11 117.6 . . ? 
O2 C12 O3 123.3(2) . . ? 
O2 C12 C11 123.4(2) . . ? 
O3 C12 C11 113.3(2) . . ? 
O3 C13 C14 107.1(2) . . ? 
O3 C13 H13A 110.3 . . ? 
C14 C13 H13A 110.3 . . ? 
O3 C13 H13B 110.3 . . ? 
C14 C13 H13B 110.3 . . ? 
H13A C13 H13B 108.6 . . ? 
C13 C14 H14A 109.5 . . ? 
C13 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C13 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
N1 C15 H15A 109.5 . . ? 
N1 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
N1 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
C21 C16 C17 118.85(18) . . ? 
C21 C16 C9 121.34(17) . . ? 
C17 C16 C9 119.75(17) . . ? 
C18 C17 C16 120.3(2) . . ? 
C18 C17 H17 119.8 . . ? 
C16 C17 H17 119.8 . . ? 
C19 C18 C17 120.5(2) . . ? 
C19 C18 H18 119.8 . . ? 
C17 C18 H18 119.8 . . ? 
C18 C19 C20 120.1(2) . . ? 
C18 C19 H19 119.9 . . ? 
C20 C19 H19 119.9 . . ? 
C19 C20 C21 120.3(2) . . ? 
C19 C20 H20 119.8 . . ? 
C21 C20 H20 119.8 . . ? 
C16 C21 C20 119.9(2) . . ? 
C16 C21 H21 120.0 . . ? 
C20 C21 H21 120.0 . . ? 
C6 N1 C5 111.35(15) . . ? 
C6 N1 C15 123.57(17) . . ? 
C5 N1 C15 125.07(18) . . ? 
C12 O3 C13 117.87(19) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C8 C1 C2 C3 0.0(3) . . . . ? 
C1 C2 C3 C4 0.5(4) . . . . ? 
C2 C3 C4 C5 -0.7(3) . . . . ? 
C3 C4 C5 N1 179.42(19) . . . . ? 
C3 C4 C5 C8 0.5(3) . . . . ? 
O1 C6 C7 C9 -0.7(3) . . . . ? 
N1 C6 C7 C9 179.48(17) . . . . ? 
O1 C6 C7 C8 179.59(19) . . . . ? 
N1 C6 C7 C8 -0.25(18) . . . . ? 
C2 C1 C8 C5 -0.1(3) . . . . ? 
C2 C1 C8 C7 -179.4(2) . . . . ? 
C4 C5 C8 C1 -0.1(3) . . . . ? 
N1 C5 C8 C1 -179.20(16) . . . . ? 
C4 C5 C8 C7 179.34(18) . . . . ? 
N1 C5 C8 C7 0.3(2) . . . . ? 
C9 C7 C8 C1 -0.4(4) . . . . ? 
C6 C7 C8 C1 179.3(2) . . . . ? 
C9 C7 C8 C5 -179.73(19) . . . . ? 
C6 C7 C8 C5 -0.02(19) . . . . ? 
C8 C7 C9 C10 178.15(17) . . . . ? 
C6 C7 C9 C10 -1.5(3) . . . . ? 
C8 C7 C9 C16 -2.7(3) . . . . ? 
C6 C7 C9 C16 177.67(16) . . . . ? 
C7 C9 C10 C11 178.24(19) . . . . ? 
C16 C9 C10 C11 -1.0(3) . . . . ? 
C9 C10 C11 C12 -178.86(19) . . . . ? 
C10 C11 C12 O2 173.0(2) . . . . ? 
C10 C11 C12 O3 -6.4(3) . . . . ? 
C7 C9 C16 C21 97.8(2) . . . . ? 
C10 C9 C16 C21 -83.0(2) . . . . ? 
C7 C9 C16 C17 -85.1(2) . . . . ? 
C10 C9 C16 C17 94.1(2) . . . . ? 
C21 C16 C17 C18 -0.9(3) . . . . ? 
C9 C16 C17 C18 -178.11(19) . . . . ? 
C16 C17 C18 C19 0.1(4) . . . . ? 
C17 C18 C19 C20 0.4(4) . . . . ? 
C18 C19 C20 C21 -0.2(4) . . . . ? 
C17 C16 C21 C20 1.1(3) . . . . ? 
C9 C16 C21 C20 178.3(2) . . . . ? 
C19 C20 C21 C16 -0.6(4) . . . . ? 
O1 C6 N1 C5 -179.42(18) . . . . ? 
C7 C6 N1 C5 0.4(2) . . . . ? 
O1 C6 N1 C15 -0.1(3) . . . . ? 
C7 C6 N1 C15 179.78(16) . . . . ? 
C4 C5 N1 C6 -179.5(2) . . . . ? 
C8 C5 N1 C6 -0.5(2) . . . . ? 
C4 C5 N1 C15 1.2(3) . . . . ? 
C8 C5 N1 C15 -179.80(17) . . . . ? 
O2 C12 O3 C13 -0.1(3) . . . . ? 
C11 C12 O3 C13 179.30(19) . . . . ? 
C14 C13 O3 C12 -176.5(2) . . . . ? 
  
_refine_diff_density_max    0.223 
_refine_diff_density_min   -0.179 
_refine_diff_density_rms    0.055 
  
  
  
 
data_18 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C24 H19 N O2' 
_chemical_formula_weight          353.40 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/n' 
_space_group_name_Hall            '-P 2yn' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    14.2530(6) 
_cell_length_b                    8.2293(3) 
_cell_length_c                    16.3693(8) 
_cell_angle_alpha                 90 
_cell_angle_beta                  98.613(2) 
_cell_angle_gamma                 90 
_cell_volume                      1898.34(14) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     6323 
_cell_measurement_theta_min       2.52 
_cell_measurement_theta_max       26.57 
  
_exptl_crystal_description        Block 
_exptl_crystal_colour             red 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.237 
_exptl_crystal_F_000              744 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.250 
_exptl_crystal_size_mid           0.220 
_exptl_crystal_size_min           0.100 
_exptl_absorpt_coefficient_mu     0.078 
_shelx_estimated_absorpt_T_min    0.981 
_shelx_estimated_absorpt_T_max    0.992 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             14458 
_diffrn_reflns_av_unetI/netI      0.0177 
_diffrn_reflns_av_R_equivalents   0.0203 
_diffrn_reflns_limit_h_min        -16 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          1.768 
_diffrn_reflns_theta_max          24.982 
_diffrn_reflns_theta_full         24.982 
_diffrn_measured_fraction_theta_max   1.000 
_diffrn_measured_fraction_theta_full  1.000 
_diffrn_reflns_Laue_measured_fraction_max    1.000 
_diffrn_reflns_Laue_measured_fraction_full   1.000 
_diffrn_reflns_point_group_measured_fraction_max   1.000 
_diffrn_reflns_point_group_measured_fraction_full  1.000 
_reflns_number_total              3339 
_reflns_number_gt                 2645 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0407P)²+0.5137P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014' 
_refine_ls_extinction_coef        0.0105(11) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3339 
_refine_ls_number_parameters      250 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0529 
_refine_ls_R_factor_gt            0.0390 
_refine_ls_wR_factor_ref          0.1049 
_refine_ls_wR_factor_gt           0.0930 
_refine_ls_goodness_of_fit_ref    1.052 
_refine_ls_restrained_S_all       1.052 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.26060(10) -0.2250(2) 0.47544(10) 0.0496(4) Uani 1 1 d . . . . . 
C2 C 0.17040(11) -0.1632(2) 0.47786(11) 0.0617(5) Uani 1 1 d . . . . . 
H2 H 0.1525 -0.0637 0.4535 0.074 Uiso 1 1 calc R U . . . 
C3 C 0.10727(13) -0.2517(3) 0.51702(13) 0.0730(6) Uani 1 1 d . . . . . 
H3 H 0.0468 -0.2108 0.5187 0.088 Uiso 1 1 calc R U . . . 
C4 C 0.13270(13) -0.3989(3) 0.55331(13) 0.0739(6) Uani 1 1 d . . . . . 
H4 H 0.0889 -0.4569 0.5785 0.089 Uiso 1 1 calc R U . . . 
C5 C 0.22269(13) -0.4622(2) 0.55295(12) 0.0669(5) Uani 1 1 d . . . . . 
H5 H 0.2404 -0.5612 0.5780 0.080 Uiso 1 1 calc R U . . . 
C6 C 0.28506(11) -0.3732(2) 0.51422(10) 0.0536(4) Uani 1 1 d . . . . . 
C7 C 0.41962(11) -0.2919(2) 0.46624(10) 0.0507(4) Uani 1 1 d . . . . . 
C8 C 0.34462(10) -0.16541(19) 0.44271(10) 0.0467(4) Uani 1 1 d . . . . . 
C9 C 0.35459(10) -0.03101(19) 0.39653(9) 0.0461(4) Uani 1 1 d . . . . . 
C10 C 0.44350(10) 0.01803(19) 0.37174(10) 0.0491(4) Uani 1 1 d . . . . . 
H10 H 0.4988 -0.0310 0.3978 0.059 Uiso 1 1 calc R U . . . 
C11 C 0.45124(11) 0.12939(19) 0.31370(10) 0.0500(4) Uani 1 1 d . . . . . 
H11 H 0.3959 0.1831 0.2913 0.060 Uiso 1 1 calc R U . . . 
C12 C 0.53757(11) 0.17496(18) 0.28206(10) 0.0469(4) Uani 1 1 d . . . . . 
C13 C 0.62714(11) 0.1329(2) 0.32156(10) 0.0539(4) Uani 1 1 d . . . . . 
H13 H 0.6329 0.0798 0.3722 0.065 Uiso 1 1 calc R U . . . 
C14 C 0.70792(11) 0.1675(2) 0.28794(11) 0.0560(4) Uani 1 1 d . . . . . 
H14 H 0.7672 0.1382 0.3158 0.067 Uiso 1 1 calc R U . . . 
C15 C 0.70051(11) 0.24545(19) 0.21308(11) 0.0513(4) Uani 1 1 d . . . . . 
C16 C 0.61254(12) 0.2927(2) 0.17327(12) 0.0622(5) Uani 1 1 d . . . . . 
H16 H 0.6075 0.3480 0.1232 0.075 Uiso 1 1 calc R U . . . 
C17 C 0.53243(12) 0.2582(2) 0.20734(11) 0.0592(5) Uani 1 1 d . . . . . 
H17 H 0.4736 0.2911 0.1800 0.071 Uiso 1 1 calc R U . . . 
C18 C 0.86653(13) 0.2240(3) 0.21058(14) 0.0853(7) Uani 1 1 d . . . . . 
H18A H 0.8836 0.2766 0.2631 0.128 Uiso 1 1 calc R U . . . 
H18B H 0.9128 0.2494 0.1755 0.128 Uiso 1 1 calc R U . . . 
H18C H 0.8645 0.1086 0.2185 0.128 Uiso 1 1 calc R U . . . 
C19 C 0.26945(10) 0.06928(19) 0.36532(10) 0.0481(4) Uani 1 1 d . . . . . 
C20 C 0.25123(13) 0.2129(2) 0.40288(13) 0.0727(6) Uani 1 1 d . . . . . 
H20 H 0.2929 0.2497 0.4483 0.087 Uiso 1 1 calc R U . . . 
C21 C 0.17145(14) 0.3030(3) 0.37361(17) 0.0882(7) Uani 1 1 d . . . . . 
H21 H 0.1592 0.3988 0.4002 0.106 Uiso 1 1 calc R U . . . 
C22 C 0.11098(14) 0.2529(3) 0.30653(16) 0.0809(7) Uani 1 1 d . . . . . 
H22 H 0.0572 0.3139 0.2874 0.097 Uiso 1 1 calc R U . . . 
C23 C 0.12910(13) 0.1126(3) 0.26704(13) 0.0762(6) Uani 1 1 d . . . . . 
H23 H 0.0882 0.0791 0.2204 0.091 Uiso 1 1 calc R U . . . 
C24 C 0.20836(12) 0.0202(2) 0.29645(11) 0.0623(5) Uani 1 1 d . . . . . 
H24 H 0.2203 -0.0754 0.2695 0.075 Uiso 1 1 calc R U . . . 
N1 N 0.37916(10) -0.41052(19) 0.50716(10) 0.0579(4) Uani 1 1 d . . . . . 
O1 O 0.50145(8) -0.29779(14) 0.45060(8) 0.0626(3) Uani 1 1 d . . . . . 
O2 O 0.77580(8) 0.27966(15) 0.17307(8) 0.0652(4) Uani 1 1 d . . . . . 
H1N H 0.4104(13) -0.502(2) 0.5259(12) 0.077(6) Uiso 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 C2 1.389(2) . ? 
C1 C6 1.395(2) . ? 
C1 C8 1.468(2) . ? 
C2 C3 1.387(2) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.374(3) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.385(3) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.377(2) . ? 
C5 H5 0.9300 . ? 
C6 N1 1.397(2) . ? 
C7 O1 1.2320(18) . ? 
C7 N1 1.360(2) . ? 
C7 C8 1.500(2) . ? 
C8 C9 1.359(2) . ? 
C9 C10 1.445(2) . ? 
C9 C19 1.493(2) . ? 
C10 C11 1.336(2) . ? 
C10 H10 0.9300 . ? 
C11 C12 1.454(2) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.386(2) . ? 
C12 C17 1.394(2) . ? 
C13 C14 1.378(2) . ? 
C13 H13 0.9300 . ? 
C14 C15 1.373(2) . ? 
C14 H14 0.9300 . ? 
C15 O2 1.3676(18) . ? 
C15 C16 1.380(2) . ? 
C16 C17 1.373(2) . ? 
C16 H16 0.9300 . ? 
C17 H17 0.9300 . ? 
C18 O2 1.422(2) . ? 
C18 H18A 0.9600 . ? 
C18 H18B 0.9600 . ? 
C18 H18C 0.9600 . ? 
C19 C20 1.375(2) . ? 
C19 C24 1.378(2) . ? 
C20 C21 1.382(3) . ? 
C20 H20 0.9300 . ? 
C21 C22 1.355(3) . ? 
C21 H21 0.9300 . ? 
C22 C23 1.366(3) . ? 
C22 H22 0.9300 . ? 
C23 C24 1.387(3) . ? 
C23 H23 0.9300 . ? 
C24 H24 0.9300 . ? 
N1 H1N 0.908(19) . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 C6 118.47(15) . . ? 
C2 C1 C8 134.22(16) . . ? 
C6 C1 C8 107.24(13) . . ? 
C3 C2 C1 119.23(18) . . ? 
C3 C2 H2 120.4 . . ? 
C1 C2 H2 120.4 . . ? 
C4 C3 C2 121.03(18) . . ? 
C4 C3 H3 119.5 . . ? 
C2 C3 H3 119.5 . . ? 
C3 C4 C5 120.94(17) . . ? 
C3 C4 H4 119.5 . . ? 
C5 C4 H4 119.5 . . ? 
C6 C5 C4 117.65(18) . . ? 
C6 C5 H5 121.2 . . ? 
C4 C5 H5 121.2 . . ? 
C5 C6 C1 122.66(16) . . ? 
C5 C6 N1 127.94(17) . . ? 
C1 C6 N1 109.39(14) . . ? 
O1 C7 N1 123.96(15) . . ? 
O1 C7 C8 129.36(15) . . ? 
N1 C7 C8 106.62(13) . . ? 
C9 C8 C1 129.35(14) . . ? 
C9 C8 C7 125.28(13) . . ? 
C1 C8 C7 105.26(13) . . ? 
C8 C9 C10 123.55(14) . . ? 
C8 C9 C19 119.53(13) . . ? 
C10 C9 C19 116.85(14) . . ? 
C11 C10 C9 124.09(15) . . ? 
C11 C10 H10 118.0 . . ? 
C9 C10 H10 118.0 . . ? 
C10 C11 C12 126.48(15) . . ? 
C10 C11 H11 116.8 . . ? 
C12 C11 H11 116.8 . . ? 
C13 C12 C17 117.11(14) . . ? 
C13 C12 C11 122.61(15) . . ? 
C17 C12 C11 120.22(14) . . ? 
C14 C13 C12 121.90(16) . . ? 
C14 C13 H13 119.1 . . ? 
C12 C13 H13 119.1 . . ? 
C15 C14 C13 119.72(15) . . ? 
C15 C14 H14 120.1 . . ? 
C13 C14 H14 120.1 . . ? 
O2 C15 C14 124.24(15) . . ? 
O2 C15 C16 116.01(15) . . ? 
C14 C15 C16 119.75(15) . . ? 
C17 C16 C15 120.14(16) . . ? 
C17 C16 H16 119.9 . . ? 
C15 C16 H16 119.9 . . ? 
C16 C17 C12 121.34(16) . . ? 
C16 C17 H17 119.3 . . ? 
C12 C17 H17 119.3 . . ? 
O2 C18 H18A 109.5 . . ? 
O2 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
O2 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C20 C19 C24 118.64(16) . . ? 
C20 C19 C9 121.36(15) . . ? 
C24 C19 C9 119.98(15) . . ? 
C19 C20 C21 120.45(19) . . ? 
C19 C20 H20 119.8 . . ? 
C21 C20 H20 119.8 . . ? 
C22 C21 C20 120.6(2) . . ? 
C22 C21 H21 119.7 . . ? 
C20 C21 H21 119.7 . . ? 
C21 C22 C23 119.87(19) . . ? 
C21 C22 H22 120.1 . . ? 
C23 C22 H22 120.1 . . ? 
C22 C23 C24 120.05(19) . . ? 
C22 C23 H23 120.0 . . ? 
C24 C23 H23 120.0 . . ? 
C19 C24 C23 120.37(19) . . ? 
C19 C24 H24 119.8 . . ? 
C23 C24 H24 119.8 . . ? 
C7 N1 C6 111.47(14) . . ? 
C7 N1 H1N 122.8(12) . . ? 
C6 N1 H1N 125.7(12) . . ? 
C15 O2 C18 117.07(15) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C6 C1 C2 C3 -1.3(3) . . . . ? 
C8 C1 C2 C3 -177.91(18) . . . . ? 
C1 C2 C3 C4 0.1(3) . . . . ? 
C2 C3 C4 C5 1.0(3) . . . . ? 
C3 C4 C5 C6 -0.7(3) . . . . ? 
C4 C5 C6 C1 -0.6(3) . . . . ? 
C4 C5 C6 N1 178.83(17) . . . . ? 
C2 C1 C6 C5 1.6(3) . . . . ? 
C8 C1 C6 C5 179.07(16) . . . . ? 
C2 C1 C6 N1 -177.92(15) . . . . ? 
C8 C1 C6 N1 -0.45(18) . . . . ? 
C2 C1 C8 C9 -6.9(3) . . . . ? 
C6 C1 C8 C9 176.21(16) . . . . ? 
C2 C1 C8 C7 176.73(18) . . . . ? 
C6 C1 C8 C7 -0.16(17) . . . . ? 
O1 C7 C8 C9 1.4(3) . . . . ? 
N1 C7 C8 C9 -175.83(15) . . . . ? 
O1 C7 C8 C1 177.95(17) . . . . ? 
N1 C7 C8 C1 0.73(17) . . . . ? 
C1 C8 C9 C10 176.76(15) . . . . ? 
C7 C8 C9 C10 -7.5(2) . . . . ? 
C1 C8 C9 C19 -6.4(3) . . . . ? 
C7 C8 C9 C19 169.32(15) . . . . ? 
C8 C9 C10 C11 166.23(16) . . . . ? 
C19 C9 C10 C11 -10.7(2) . . . . ? 
C9 C10 C11 C12 -175.20(15) . . . . ? 
C10 C11 C12 C13 -14.7(3) . . . . ? 
C10 C11 C12 C17 162.41(17) . . . . ? 
C17 C12 C13 C14 -1.7(3) . . . . ? 
C11 C12 C13 C14 175.57(15) . . . . ? 
C12 C13 C14 C15 -0.2(3) . . . . ? 
C13 C14 C15 O2 -177.38(15) . . . . ? 
C13 C14 C15 C16 1.9(3) . . . . ? 
O2 C15 C16 C17 177.67(16) . . . . ? 
C14 C15 C16 C17 -1.7(3) . . . . ? 
C15 C16 C17 C12 -0.3(3) . . . . ? 
C13 C12 C17 C16 1.9(3) . . . . ? 
C11 C12 C17 C16 -175.40(16) . . . . ? 
C8 C9 C19 C20 101.8(2) . . . . ? 
C10 C9 C19 C20 -81.1(2) . . . . ? 
C8 C9 C19 C24 -79.6(2) . . . . ? 
C10 C9 C19 C24 97.41(18) . . . . ? 
C24 C19 C20 C21 2.2(3) . . . . ? 
C9 C19 C20 C21 -179.25(19) . . . . ? 
C19 C20 C21 C22 -1.3(4) . . . . ? 
C20 C21 C22 C23 -0.4(4) . . . . ? 
C21 C22 C23 C24 1.1(3) . . . . ? 
C20 C19 C24 C23 -1.4(3) . . . . ? 
C9 C19 C24 C23 180.00(16) . . . . ? 
C22 C23 C24 C19 -0.2(3) . . . . ? 
O1 C7 N1 C6 -178.45(16) . . . . ? 
C8 C7 N1 C6 -1.04(19) . . . . ? 
C5 C6 N1 C7 -178.51(18) . . . . ? 
C1 C6 N1 C7 1.0(2) . . . . ? 
C14 C15 O2 C18 2.8(3) . . . . ? 
C16 C15 O2 C18 -176.53(17) . . . . ? 
  
_refine_diff_density_max    0.144 
_refine_diff_density_min   -0.116 
_refine_diff_density_rms    0.030 
  
  
  
 
data_4cl 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C23 H15 Cl O2' 
_chemical_formula_weight          358.80 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.1484   0.1585 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            7 
_space_group_name_H-M_alt         'P c' 
_space_group_name_Hall            'P -2yc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 'x, -y, z+1/2' 
  
_cell_length_a                    9.7179(9) 
_cell_length_b                    12.4696(12) 
_cell_length_c                    7.5883(8) 
_cell_angle_alpha                 90 
_cell_angle_beta                  106.874(5) 
_cell_angle_gamma                 90 
_cell_volume                      879.95(15) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     1424 
_cell_measurement_theta_min       2.73 
_cell_measurement_theta_max       20.49 
  
_exptl_crystal_description        Rectangular 
_exptl_crystal_colour             red 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.354 
_exptl_crystal_F_000              372 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.250 
_exptl_crystal_size_mid           0.220 
_exptl_crystal_size_min           0.100 
_exptl_absorpt_coefficient_mu     0.231 
_shelx_estimated_absorpt_T_min    0.944 
_shelx_estimated_absorpt_T_max    0.977 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             5733 
_diffrn_reflns_av_unetI/netI      0.0485 
_diffrn_reflns_av_R_equivalents   0.0306 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        8 
_diffrn_reflns_theta_min          1.633 
_diffrn_reflns_theta_max          24.990 
_diffrn_reflns_theta_full         24.990 
_diffrn_measured_fraction_theta_max   0.997 
_diffrn_measured_fraction_theta_full  0.997 
_diffrn_reflns_Laue_measured_fraction_max    0.997 
_diffrn_reflns_Laue_measured_fraction_full   0.997 
_diffrn_reflns_point_group_measured_fraction_max   0.882 
_diffrn_reflns_point_group_measured_fraction_full  0.882 
_reflns_number_total              2741 
_reflns_number_gt                 2049 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.762 
_reflns_Friedel_fraction_max      0.766 
_reflns_Friedel_fraction_full     0.766 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0576P)²] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014' 
_refine_ls_extinction_coef        0.013(4) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 746 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    -0.02(5) 
_chemical_absolute_configuration  ? 
_refine_ls_number_reflns          2741 
_refine_ls_number_parameters      236 
_refine_ls_number_restraints      2 
_refine_ls_R_factor_all           0.0662 
_refine_ls_R_factor_gt            0.0426 
_refine_ls_wR_factor_ref          0.1142 
_refine_ls_wR_factor_gt           0.1006 
_refine_ls_goodness_of_fit_ref    1.041 
_refine_ls_restrained_S_all       1.040 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.3281(6) 0.6779(4) 0.1689(7) 0.0565(14) Uani 1 1 d . . . . . 
H1 H 0.2426 0.6829 0.0741 0.068 Uiso 1 1 calc R U . . . 
C2 C 0.4114(6) 0.7677(4) 0.2212(7) 0.0602(14) Uani 1 1 d . . . . . 
H2 H 0.3828 0.8327 0.1617 0.072 Uiso 1 1 calc R U . . . 
C3 C 0.5369(5) 0.7609(4) 0.3617(7) 0.0545(14) Uani 1 1 d . . . . . 
C4 C 0.5835(5) 0.6650(4) 0.4462(8) 0.0590(14) Uani 1 1 d . . . . . 
H4 H 0.6708 0.6605 0.5381 0.071 Uiso 1 1 calc R U . . . 
C5 C 0.4990(5) 0.5755(4) 0.3926(7) 0.0520(13) Uani 1 1 d . . . . . 
H5 H 0.5300 0.5104 0.4504 0.062 Uiso 1 1 calc R U . . . 
C6 C 0.3687(5) 0.5793(4) 0.2546(6) 0.0437(12) Uani 1 1 d . . . . . 
C7 C 0.2839(5) 0.4820(4) 0.2047(7) 0.0458(12) Uani 1 1 d . . . . . 
H7 H 0.3184 0.4209 0.2736 0.055 Uiso 1 1 calc R U . . . 
C8 C 0.1611(5) 0.4721(4) 0.0694(6) 0.0461(12) Uani 1 1 d . . . . . 
H8 H 0.1197 0.5342 0.0091 0.055 Uiso 1 1 calc R U . . . 
C9 C 0.0876(5) 0.3716(4) 0.0096(6) 0.0423(11) Uani 1 1 d . . . . . 
C10 C -0.0303(5) 0.3661(4) -0.1438(6) 0.0418(11) Uani 1 1 d . . . . . 
C11 C -0.0973(5) 0.2745(4) -0.2525(6) 0.0474(12) Uani 1 1 d . . . . . 
C12 C -0.0657(6) 0.1660(4) -0.2544(8) 0.0577(14) Uani 1 1 d . . . . . 
H12 H 0.0103 0.1367 -0.1628 0.069 Uiso 1 1 calc R U . . . 
C13 C -0.1483(6) 0.1022(4) -0.3932(8) 0.0673(16) Uani 1 1 d . . . . . 
H13 H -0.1279 0.0294 -0.3948 0.081 Uiso 1 1 calc R U . . . 
C14 C -0.2616(7) 0.1454(5) -0.5309(8) 0.0786(19) Uani 1 1 d . . . . . 
H14 H -0.3160 0.1011 -0.6237 0.094 Uiso 1 1 calc R U . . . 
C15 C -0.2951(6) 0.2531(5) -0.5326(8) 0.0732(17) Uani 1 1 d . . . . . 
H15 H -0.3710 0.2826 -0.6243 0.088 Uiso 1 1 calc R U . . . 
C16 C -0.2122(5) 0.3136(4) -0.3946(8) 0.0538(13) Uani 1 1 d . . . . . 
C17 C -0.1143(5) 0.4609(4) -0.2362(7) 0.0495(13) Uani 1 1 d . . . . . 
C18 C 0.1433(5) 0.2710(4) 0.1092(6) 0.0424(11) Uani 1 1 d . . . . . 
C19 C 0.2725(6) 0.2259(4) 0.1066(7) 0.0525(13) Uani 1 1 d . . . . . 
H19 H 0.3290 0.2607 0.0442 0.063 Uiso 1 1 calc R U . . . 
C20 C 0.3192(6) 0.1300(5) 0.1951(8) 0.0607(15) Uani 1 1 d . . . . . 
H20 H 0.4056 0.1000 0.1901 0.073 Uiso 1 1 calc R U . . . 
C21 C 0.2383(7) 0.0794(4) 0.2898(8) 0.0643(15) Uani 1 1 d . . . . . 
H21 H 0.2692 0.0147 0.3491 0.077 Uiso 1 1 calc R U . . . 
C22 C 0.1108(7) 0.1246(4) 0.2972(7) 0.0639(15) Uani 1 1 d . . . . . 
H22 H 0.0563 0.0906 0.3633 0.077 Uiso 1 1 calc R U . . . 
C23 C 0.0634(5) 0.2191(4) 0.2079(7) 0.0527(13) Uani 1 1 d . . . . . 
H23 H -0.0231 0.2486 0.2136 0.063 Uiso 1 1 calc R U . . . 
Cl1 Cl 0.63573(19) 0.87624(13) 0.4360(2) 0.0904(6) Uani 1 1 d . . . . . 
O1 O -0.2270(4) 0.4240(3) -0.3806(5) 0.0588(9) Uani 1 1 d . . . . . 
O2 O -0.1036(4) 0.5553(3) -0.2043(5) 0.0639(10) Uani 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 C2 1.371(7) . ? 
C1 C6 1.393(7) . ? 
C1 H1 0.9300 . ? 
C2 C3 1.371(7) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.370(7) . ? 
C3 Cl1 1.730(5) . ? 
C4 C5 1.376(7) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.390(6) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.454(6) . ? 
C7 C8 1.335(7) . ? 
C7 H7 0.9300 . ? 
C8 C9 1.448(6) . ? 
C8 H8 0.9300 . ? 
C9 C10 1.378(6) . ? 
C9 C18 1.483(6) . ? 
C10 C11 1.448(6) . ? 
C10 C17 1.490(7) . ? 
C11 C12 1.389(7) . ? 
C11 C16 1.395(7) . ? 
C12 C13 1.376(7) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.388(8) . ? 
C13 H13 0.9300 . ? 
C14 C15 1.381(8) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.351(8) . ? 
C15 H15 0.9300 . ? 
C16 O1 1.391(6) . ? 
C17 O2 1.200(6) . ? 
C17 O1 1.384(6) . ? 
C18 C19 1.381(7) . ? 
C18 C23 1.386(7) . ? 
C19 C20 1.382(7) . ? 
C19 H19 0.9300 . ? 
C20 C21 1.364(8) . ? 
C20 H20 0.9300 . ? 
C21 C22 1.377(8) . ? 
C21 H21 0.9300 . ? 
C22 C23 1.371(7) . ? 
C22 H22 0.9300 . ? 
C23 H23 0.9300 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 C6 121.5(5) . . ? 
C2 C1 H1 119.2 . . ? 
C6 C1 H1 119.2 . . ? 
C3 C2 C1 119.5(5) . . ? 
C3 C2 H2 120.3 . . ? 
C1 C2 H2 120.3 . . ? 
C4 C3 C2 121.1(5) . . ? 
C4 C3 Cl1 119.7(4) . . ? 
C2 C3 Cl1 119.2(4) . . ? 
C3 C4 C5 118.8(5) . . ? 
C3 C4 H4 120.6 . . ? 
C5 C4 H4 120.6 . . ? 
C4 C5 C6 122.0(5) . . ? 
C4 C5 H5 119.0 . . ? 
C6 C5 H5 119.0 . . ? 
C5 C6 C1 117.0(4) . . ? 
C5 C6 C7 119.4(4) . . ? 
C1 C6 C7 123.5(4) . . ? 
C8 C7 C6 126.2(4) . . ? 
C8 C7 H7 116.9 . . ? 
C6 C7 H7 116.9 . . ? 
C7 C8 C9 124.8(4) . . ? 
C7 C8 H8 117.6 . . ? 
C9 C8 H8 117.6 . . ? 
C10 C9 C8 121.4(4) . . ? 
C10 C9 C18 118.6(4) . . ? 
C8 C9 C18 119.9(4) . . ? 
C9 C10 C11 130.3(4) . . ? 
C9 C10 C17 124.4(4) . . ? 
C11 C10 C17 105.3(4) . . ? 
C12 C11 C16 117.5(4) . . ? 
C12 C11 C10 135.2(4) . . ? 
C16 C11 C10 106.9(4) . . ? 
C13 C12 C11 119.3(5) . . ? 
C13 C12 H12 120.4 . . ? 
C11 C12 H12 120.4 . . ? 
C12 C13 C14 120.7(5) . . ? 
C12 C13 H13 119.6 . . ? 
C14 C13 H13 119.6 . . ? 
C15 C14 C13 121.2(5) . . ? 
C15 C14 H14 119.4 . . ? 
C13 C14 H14 119.4 . . ? 
C16 C15 C14 116.7(5) . . ? 
C16 C15 H15 121.6 . . ? 
C14 C15 H15 121.6 . . ? 
C15 C16 O1 124.1(5) . . ? 
C15 C16 C11 124.5(5) . . ? 
O1 C16 C11 111.3(4) . . ? 
O2 C17 O1 119.2(4) . . ? 
O2 C17 C10 132.8(5) . . ? 
O1 C17 C10 108.0(4) . . ? 
C19 C18 C23 118.2(4) . . ? 
C19 C18 C9 122.4(4) . . ? 
C23 C18 C9 119.4(4) . . ? 
C18 C19 C20 121.1(5) . . ? 
C18 C19 H19 119.4 . . ? 
C20 C19 H19 119.4 . . ? 
C21 C20 C19 119.9(5) . . ? 
C21 C20 H20 120.1 . . ? 
C19 C20 H20 120.1 . . ? 
C20 C21 C22 119.7(5) . . ? 
C20 C21 H21 120.2 . . ? 
C22 C21 H21 120.2 . . ? 
C23 C22 C21 120.6(5) . . ? 
C23 C22 H22 119.7 . . ? 
C21 C22 H22 119.7 . . ? 
C22 C23 C18 120.5(5) . . ? 
C22 C23 H23 119.7 . . ? 
C18 C23 H23 119.7 . . ? 
C17 O1 C16 108.3(4) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C6 C1 C2 C3 -0.5(8) . . . . ? 
C1 C2 C3 C4 2.6(8) . . . . ? 
C1 C2 C3 Cl1 -176.1(4) . . . . ? 
C2 C3 C4 C5 -2.6(8) . . . . ? 
Cl1 C3 C4 C5 176.1(4) . . . . ? 
C3 C4 C5 C6 0.6(8) . . . . ? 
C4 C5 C6 C1 1.4(7) . . . . ? 
C4 C5 C6 C7 -179.7(5) . . . . ? 
C2 C1 C6 C5 -1.5(7) . . . . ? 
C2 C1 C6 C7 179.7(5) . . . . ? 
C5 C6 C7 C8 -176.3(5) . . . . ? 
C1 C6 C7 C8 2.5(8) . . . . ? 
C6 C7 C8 C9 172.7(5) . . . . ? 
C7 C8 C9 C10 -172.9(5) . . . . ? 
C7 C8 C9 C18 4.2(7) . . . . ? 
C8 C9 C10 C11 163.1(4) . . . . ? 
C18 C9 C10 C11 -14.1(7) . . . . ? 
C8 C9 C10 C17 -14.8(7) . . . . ? 
C18 C9 C10 C17 168.0(4) . . . . ? 
C9 C10 C11 C12 -5.7(9) . . . . ? 
C17 C10 C11 C12 172.6(5) . . . . ? 
C9 C10 C11 C16 -179.1(5) . . . . ? 
C17 C10 C11 C16 -0.9(5) . . . . ? 
C16 C11 C12 C13 -0.5(8) . . . . ? 
C10 C11 C12 C13 -173.3(5) . . . . ? 
C11 C12 C13 C14 0.3(9) . . . . ? 
C12 C13 C14 C15 -0.1(10) . . . . ? 
C13 C14 C15 C16 0.1(9) . . . . ? 
C14 C15 C16 O1 176.9(5) . . . . ? 
C14 C15 C16 C11 -0.3(9) . . . . ? 
C12 C11 C16 C15 0.5(8) . . . . ? 
C10 C11 C16 C15 175.3(5) . . . . ? 
C12 C11 C16 O1 -177.0(4) . . . . ? 
C10 C11 C16 O1 -2.2(6) . . . . ? 
C9 C10 C17 O2 -0.8(8) . . . . ? 
C11 C10 C17 O2 -179.2(5) . . . . ? 
C9 C10 C17 O1 -178.0(4) . . . . ? 
C11 C10 C17 O1 3.6(5) . . . . ? 
C10 C9 C18 C19 109.5(5) . . . . ? 
C8 C9 C18 C19 -67.7(6) . . . . ? 
C10 C9 C18 C23 -70.0(6) . . . . ? 
C8 C9 C18 C23 112.8(5) . . . . ? 
C23 C18 C19 C20 1.9(7) . . . . ? 
C9 C18 C19 C20 -177.6(5) . . . . ? 
C18 C19 C20 C21 -1.2(8) . . . . ? 
C19 C20 C21 C22 -0.3(8) . . . . ? 
C20 C21 C22 C23 1.0(8) . . . . ? 
C21 C22 C23 C18 -0.2(8) . . . . ? 
C19 C18 C23 C22 -1.2(7) . . . . ? 
C9 C18 C23 C22 178.3(4) . . . . ? 
O2 C17 O1 C16 177.3(4) . . . . ? 
C10 C17 O1 C16 -5.0(5) . . . . ? 
C15 C16 O1 C17 -172.9(5) . . . . ? 
C11 C16 O1 C17 4.6(6) . . . . ? 
  
_refine_diff_density_max    0.151 
_refine_diff_density_min   -0.162 
_refine_diff_density_rms    0.037 
  
  
  
 
data_np 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C27 H25 N O4' 
_chemical_formula_weight          427.48 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    8.1334(3) 
_cell_length_b                    31.8582(16) 
_cell_length_c                    9.2310(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  110.330(2) 
_cell_angle_gamma                 90 
_cell_volume                      2242.89(19) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     4048 
_cell_measurement_theta_min       2.44 
_cell_measurement_theta_max       21.93 
  
_exptl_crystal_description        Rectangular 
_exptl_crystal_colour             red 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.266 
_exptl_crystal_F_000              904 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.250 
_exptl_crystal_size_mid           0.220 
_exptl_crystal_size_min           0.100 
_exptl_absorpt_coefficient_mu     0.085 
_shelx_estimated_absorpt_T_min    0.979 
_shelx_estimated_absorpt_T_max    0.992 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             13204 
_diffrn_reflns_av_unetI/netI      0.0393 
_diffrn_reflns_av_R_equivalents   0.0323 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -28 
_diffrn_reflns_limit_k_max        37 
_diffrn_reflns_limit_l_min        -10 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          2.438 
_diffrn_reflns_theta_max          24.997 
_diffrn_reflns_theta_full         24.997 
_diffrn_measured_fraction_theta_max   0.999 
_diffrn_measured_fraction_theta_full  0.999 
_diffrn_reflns_Laue_measured_fraction_max    0.999 
_diffrn_reflns_Laue_measured_fraction_full   0.999 
_diffrn_reflns_point_group_measured_fraction_max   0.999 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
_reflns_number_total              3944 
_reflns_number_gt                 2625 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0466P)²+0.6707P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014' 
_refine_ls_extinction_coef        0.0064(10) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3944 
_refine_ls_number_parameters      294 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0808 
_refine_ls_R_factor_gt            0.0472 
_refine_ls_wR_factor_ref          0.1220 
_refine_ls_wR_factor_gt           0.1025 
_refine_ls_goodness_of_fit_ref    1.029 
_refine_ls_restrained_S_all       1.029 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C -0.1308(3) 0.03867(7) 0.8567(2) 0.0485(6) Uani 1 1 d . . . . . 
C2 C -0.2695(3) 0.02456(9) 0.8967(3) 0.0654(7) Uani 1 1 d . . . . . 
H2 H -0.3175 -0.0019 0.8675 0.079 Uiso 1 1 calc R U . . . 
C3 C -0.3348(3) 0.05127(10) 0.9820(3) 0.0695(8) Uani 1 1 d . . . . . 
H3 H -0.4289 0.0426 1.0098 0.083 Uiso 1 1 calc R U . . . 
C4 C -0.2636(3) 0.09037(9) 1.0265(3) 0.0622(7) Uani 1 1 d . . . . . 
H4 H -0.3092 0.1076 1.0847 0.075 Uiso 1 1 calc R U . . . 
C5 C -0.1249(3) 0.10430(8) 0.9855(2) 0.0506(6) Uani 1 1 d . . . . . 
H5 H -0.0781 0.1309 1.0149 0.061 Uiso 1 1 calc R U . . . 
C6 C -0.0556(3) 0.07838(7) 0.9003(2) 0.0428(5) Uani 1 1 d . . . . . 
C7 C 0.0838(3) 0.08300(7) 0.8349(2) 0.0416(5) Uani 1 1 d . . . . . 
C8 C 0.0841(3) 0.04245(7) 0.7516(2) 0.0486(6) Uani 1 1 d . . . . . 
C9 C 0.1899(2) 0.11624(6) 0.8390(2) 0.0394(5) Uani 1 1 d . . . . . 
C10 C 0.3072(3) 0.11721(7) 0.7521(2) 0.0445(5) Uani 1 1 d . . . . . 
H10 H 0.3203 0.0926 0.7029 0.053 Uiso 1 1 calc R U . . . 
C11 C 0.3979(3) 0.15065(7) 0.7371(2) 0.0425(5) Uani 1 1 d . . . . . 
H11 H 0.3908 0.1745 0.7929 0.051 Uiso 1 1 calc R U . . . 
C12 C 0.5076(2) 0.15358(7) 0.6415(2) 0.0401(5) Uani 1 1 d . . . . . 
C13 C 0.5688(3) 0.19269(7) 0.6172(2) 0.0427(5) Uani 1 1 d . . . . . 
H13 H 0.5437 0.2162 0.6655 0.051 Uiso 1 1 calc R U . . . 
C14 C 0.6668(3) 0.19693(7) 0.5217(2) 0.0422(5) Uani 1 1 d . . . . . 
C15 C 0.7071(3) 0.16193(7) 0.4507(2) 0.0420(5) Uani 1 1 d . . . . . 
C16 C 0.6458(3) 0.12282(7) 0.4752(2) 0.0462(5) Uani 1 1 d . . . . . 
C17 C 0.5479(3) 0.11853(7) 0.5704(2) 0.0476(6) Uani 1 1 d . . . . . 
H17 H 0.5088 0.0921 0.5869 0.057 Uiso 1 1 calc R U . . . 
C18 C -0.0828(4) -0.02423(7) 0.7083(3) 0.0658(7) Uani 1 1 d . . . . . 
H18A H 0.0017 -0.0322 0.6621 0.099 Uiso 1 1 calc R U . . . 
H18B H -0.1983 -0.0251 0.6316 0.099 Uiso 1 1 calc R U . . . 
H18C H -0.0766 -0.0433 0.7904 0.099 Uiso 1 1 calc R U . . . 
C19 C 0.1843(2) 0.15413(6) 0.9315(2) 0.0387(5) Uani 1 1 d . . . . . 
C20 C 0.2869(3) 0.15615(8) 1.0859(3) 0.0589(7) Uani 1 1 d . . . . . 
H20 H 0.3605 0.1339 1.1321 0.071 Uiso 1 1 calc R U . . . 
C21 C 0.2802(3) 0.19143(10) 1.1722(3) 0.0759(9) Uani 1 1 d . . . . . 
H21 H 0.3475 0.1926 1.2767 0.091 Uiso 1 1 calc R U . . . 
C22 C 0.1749(4) 0.22439(9) 1.1037(4) 0.0755(8) Uani 1 1 d . . . . . 
H22 H 0.1721 0.2481 1.1613 0.091 Uiso 1 1 calc R U . . . 
C23 C 0.0743(4) 0.22269(8) 0.9520(3) 0.0696(8) Uani 1 1 d . . . . . 
H23 H 0.0021 0.2452 0.9061 0.084 Uiso 1 1 calc R U . . . 
C24 C 0.0787(3) 0.18782(7) 0.8661(3) 0.0531(6) Uani 1 1 d . . . . . 
H24 H 0.0093 0.1870 0.7620 0.064 Uiso 1 1 calc R U . . . 
C25 C 0.6836(4) 0.27119(8) 0.5524(3) 0.0738(8) Uani 1 1 d . . . . . 
H25A H 0.5585 0.2734 0.5218 0.111 Uiso 1 1 calc R U . . . 
H25B H 0.7287 0.2953 0.5159 0.111 Uiso 1 1 calc R U . . . 
H25C H 0.7341 0.2699 0.6630 0.111 Uiso 1 1 calc R U . . . 
C26 C 0.9707(3) 0.15231(9) 0.4024(3) 0.0706(8) Uani 1 1 d . . . . . 
H26A H 1.0390 0.1688 0.4896 0.106 Uiso 1 1 calc R U . . . 
H26B H 1.0186 0.1549 0.3213 0.106 Uiso 1 1 calc R U . . . 
H26C H 0.9736 0.1234 0.4325 0.106 Uiso 1 1 calc R U . . . 
C27 C 0.6204(4) 0.05069(8) 0.4070(3) 0.0740(8) Uani 1 1 d . . . . . 
H27A H 0.6522 0.0425 0.5134 0.111 Uiso 1 1 calc R U . . . 
H27B H 0.6668 0.0307 0.3534 0.111 Uiso 1 1 calc R U . . . 
H27C H 0.4950 0.0515 0.3603 0.111 Uiso 1 1 calc R U . . . 
N1 N -0.0455(2) 0.01793(6) 0.7695(2) 0.0528(5) Uani 1 1 d . . . . . 
O1 O 0.7276(2) 0.23418(5) 0.48788(19) 0.0623(5) Uani 1 1 d . . . . . 
O2 O 0.79462(19) 0.16683(5) 0.34891(17) 0.0561(4) Uani 1 1 d . . . . . 
O3 O 0.6891(2) 0.09036(5) 0.3985(2) 0.0706(5) Uani 1 1 d . . . . . 
O4 O 0.1797(2) 0.03112(5) 0.6820(2) 0.0699(5) Uani 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 C2 1.379(3) . ? 
C1 N1 1.397(3) . ? 
C1 C6 1.402(3) . ? 
C2 C3 1.385(4) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.375(4) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.382(3) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.388(3) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.465(3) . ? 
C7 C9 1.359(3) . ? 
C7 C8 1.504(3) . ? 
C8 O4 1.222(2) . ? 
C8 N1 1.367(3) . ? 
C9 C10 1.445(3) . ? 
C9 C19 1.489(3) . ? 
C10 C11 1.330(3) . ? 
C10 H10 0.9300 . ? 
C11 C12 1.460(3) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.388(3) . ? 
C12 C17 1.391(3) . ? 
C13 C14 1.386(3) . ? 
C13 H13 0.9300 . ? 
C14 O1 1.363(2) . ? 
C14 C15 1.388(3) . ? 
C15 O2 1.371(2) . ? 
C15 C16 1.390(3) . ? 
C16 O3 1.367(2) . ? 
C16 C17 1.382(3) . ? 
C17 H17 0.9300 . ? 
C18 N1 1.448(3) . ? 
C18 H18A 0.9600 . ? 
C18 H18B 0.9600 . ? 
C18 H18C 0.9600 . ? 
C19 C24 1.376(3) . ? 
C19 C20 1.380(3) . ? 
C20 C21 1.390(3) . ? 
C20 H20 0.9300 . ? 
C21 C22 1.364(4) . ? 
C21 H21 0.9300 . ? 
C22 C23 1.355(4) . ? 
C22 H22 0.9300 . ? 
C23 C24 1.373(3) . ? 
C23 H23 0.9300 . ? 
C24 H24 0.9300 . ? 
C25 O1 1.421(3) . ? 
C25 H25A 0.9600 . ? 
C25 H25B 0.9600 . ? 
C25 H25C 0.9600 . ? 
C26 O2 1.421(3) . ? 
C26 H26A 0.9600 . ? 
C26 H26B 0.9600 . ? 
C26 H26C 0.9600 . ? 
C27 O3 1.395(3) . ? 
C27 H27A 0.9600 . ? 
C27 H27B 0.9600 . ? 
C27 H27C 0.9600 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 N1 128.0(2) . . ? 
C2 C1 C6 122.2(2) . . ? 
N1 C1 C6 109.76(18) . . ? 
C1 C2 C3 117.6(2) . . ? 
C1 C2 H2 121.2 . . ? 
C3 C2 H2 121.2 . . ? 
C4 C3 C2 121.4(2) . . ? 
C4 C3 H3 119.3 . . ? 
C2 C3 H3 119.3 . . ? 
C3 C4 C5 120.6(2) . . ? 
C3 C4 H4 119.7 . . ? 
C5 C4 H4 119.7 . . ? 
C4 C5 C6 119.7(2) . . ? 
C4 C5 H5 120.2 . . ? 
C6 C5 H5 120.2 . . ? 
C5 C6 C1 118.51(19) . . ? 
C5 C6 C7 134.3(2) . . ? 
C1 C6 C7 107.13(18) . . ? 
C9 C7 C6 129.92(19) . . ? 
C9 C7 C8 124.75(17) . . ? 
C6 C7 C8 105.29(17) . . ? 
O4 C8 N1 123.5(2) . . ? 
O4 C8 C7 129.6(2) . . ? 
N1 C8 C7 106.90(17) . . ? 
C7 C9 C10 122.48(19) . . ? 
C7 C9 C19 120.14(17) . . ? 
C10 C9 C19 117.35(18) . . ? 
C11 C10 C9 124.9(2) . . ? 
C11 C10 H10 117.6 . . ? 
C9 C10 H10 117.6 . . ? 
C10 C11 C12 126.3(2) . . ? 
C10 C11 H11 116.9 . . ? 
C12 C11 H11 116.9 . . ? 
C13 C12 C17 119.22(18) . . ? 
C13 C12 C11 118.90(18) . . ? 
C17 C12 C11 121.85(19) . . ? 
C14 C13 C12 120.51(19) . . ? 
C14 C13 H13 119.7 . . ? 
C12 C13 H13 119.7 . . ? 
O1 C14 C13 124.41(19) . . ? 
O1 C14 C15 115.31(17) . . ? 
C13 C14 C15 120.26(19) . . ? 
O2 C15 C14 119.72(19) . . ? 
O2 C15 C16 120.97(18) . . ? 
C14 C15 C16 119.12(18) . . ? 
O3 C16 C17 124.3(2) . . ? 
O3 C16 C15 114.99(18) . . ? 
C17 C16 C15 120.69(19) . . ? 
C16 C17 C12 120.2(2) . . ? 
C16 C17 H17 119.9 . . ? 
C12 C17 H17 119.9 . . ? 
N1 C18 H18A 109.5 . . ? 
N1 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
N1 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C24 C19 C20 118.6(2) . . ? 
C24 C19 C9 121.30(18) . . ? 
C20 C19 C9 120.12(19) . . ? 
C19 C20 C21 120.0(2) . . ? 
C19 C20 H20 120.0 . . ? 
C21 C20 H20 120.0 . . ? 
C22 C21 C20 120.0(2) . . ? 
C22 C21 H21 120.0 . . ? 
C20 C21 H21 120.0 . . ? 
C23 C22 C21 120.3(2) . . ? 
C23 C22 H22 119.8 . . ? 
C21 C22 H22 119.8 . . ? 
C22 C23 C24 120.1(3) . . ? 
C22 C23 H23 119.9 . . ? 
C24 C23 H23 119.9 . . ? 
C23 C24 C19 121.0(2) . . ? 
C23 C24 H24 119.5 . . ? 
C19 C24 H24 119.5 . . ? 
O1 C25 H25A 109.5 . . ? 
O1 C25 H25B 109.5 . . ? 
H25A C25 H25B 109.5 . . ? 
O1 C25 H25C 109.5 . . ? 
H25A C25 H25C 109.5 . . ? 
H25B C25 H25C 109.5 . . ? 
O2 C26 H26A 109.5 . . ? 
O2 C26 H26B 109.5 . . ? 
H26A C26 H26B 109.5 . . ? 
O2 C26 H26C 109.5 . . ? 
H26A C26 H26C 109.5 . . ? 
H26B C26 H26C 109.5 . . ? 
O3 C27 H27A 109.5 . . ? 
O3 C27 H27B 109.5 . . ? 
H27A C27 H27B 109.5 . . ? 
O3 C27 H27C 109.5 . . ? 
H27A C27 H27C 109.5 . . ? 
H27B C27 H27C 109.5 . . ? 
C8 N1 C1 110.91(18) . . ? 
C8 N1 C18 123.28(19) . . ? 
C1 N1 C18 125.79(19) . . ? 
C14 O1 C25 117.57(17) . . ? 
C15 O2 C26 115.19(17) . . ? 
C16 O3 C27 118.38(17) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
N1 C1 C2 C3 -178.8(2) . . . . ? 
C6 C1 C2 C3 0.4(4) . . . . ? 
C1 C2 C3 C4 -0.5(4) . . . . ? 
C2 C3 C4 C5 0.6(4) . . . . ? 
C3 C4 C5 C6 -0.8(4) . . . . ? 
C4 C5 C6 C1 0.7(3) . . . . ? 
C4 C5 C6 C7 178.0(2) . . . . ? 
C2 C1 C6 C5 -0.6(3) . . . . ? 
N1 C1 C6 C5 178.76(18) . . . . ? 
C2 C1 C6 C7 -178.6(2) . . . . ? 
N1 C1 C6 C7 0.8(2) . . . . ? 
C5 C6 C7 C9 -0.5(4) . . . . ? 
C1 C6 C7 C9 177.0(2) . . . . ? 
C5 C6 C7 C8 -178.2(2) . . . . ? 
C1 C6 C7 C8 -0.7(2) . . . . ? 
C9 C7 C8 O4 3.9(4) . . . . ? 
C6 C7 C8 O4 -178.2(2) . . . . ? 
C9 C7 C8 N1 -177.5(2) . . . . ? 
C6 C7 C8 N1 0.4(2) . . . . ? 
C6 C7 C9 C10 -172.4(2) . . . . ? 
C8 C7 C9 C10 5.0(3) . . . . ? 
C6 C7 C9 C19 5.6(3) . . . . ? 
C8 C7 C9 C19 -177.05(18) . . . . ? 
C7 C9 C10 C11 171.5(2) . . . . ? 
C19 C9 C10 C11 -6.6(3) . . . . ? 
C9 C10 C11 C12 -175.34(19) . . . . ? 
C10 C11 C12 C13 168.8(2) . . . . ? 
C10 C11 C12 C17 -9.2(3) . . . . ? 
C17 C12 C13 C14 0.9(3) . . . . ? 
C11 C12 C13 C14 -177.16(18) . . . . ? 
C12 C13 C14 O1 178.02(19) . . . . ? 
C12 C13 C14 C15 -0.9(3) . . . . ? 
O1 C14 C15 O2 -3.1(3) . . . . ? 
C13 C14 C15 O2 175.92(18) . . . . ? 
O1 C14 C15 C16 -178.14(19) . . . . ? 
C13 C14 C15 C16 0.9(3) . . . . ? 
O2 C15 C16 O3 3.8(3) . . . . ? 
C14 C15 C16 O3 178.81(19) . . . . ? 
O2 C15 C16 C17 -175.80(19) . . . . ? 
C14 C15 C16 C17 -0.8(3) . . . . ? 
O3 C16 C17 C12 -178.8(2) . . . . ? 
C15 C16 C17 C12 0.8(3) . . . . ? 
C13 C12 C17 C16 -0.8(3) . . . . ? 
C11 C12 C17 C16 177.16(19) . . . . ? 
C7 C9 C19 C24 -93.2(2) . . . . ? 
C10 C9 C19 C24 84.9(2) . . . . ? 
C7 C9 C19 C20 87.2(3) . . . . ? 
C10 C9 C19 C20 -94.7(2) . . . . ? 
C24 C19 C20 C21 0.9(3) . . . . ? 
C9 C19 C20 C21 -179.5(2) . . . . ? 
C19 C20 C21 C22 -1.3(4) . . . . ? 
C20 C21 C22 C23 1.1(4) . . . . ? 
C21 C22 C23 C24 -0.4(4) . . . . ? 
C22 C23 C24 C19 0.1(4) . . . . ? 
C20 C19 C24 C23 -0.3(3) . . . . ? 
C9 C19 C24 C23 -179.9(2) . . . . ? 
O4 C8 N1 C1 178.8(2) . . . . ? 
C7 C8 N1 C1 0.0(2) . . . . ? 
O4 C8 N1 C18 0.3(4) . . . . ? 
C7 C8 N1 C18 -178.44(19) . . . . ? 
C2 C1 N1 C8 178.8(2) . . . . ? 
C6 C1 N1 C8 -0.5(3) . . . . ? 
C2 C1 N1 C18 -2.8(4) . . . . ? 
C6 C1 N1 C18 177.9(2) . . . . ? 
C13 C14 O1 C25 -1.6(3) . . . . ? 
C15 C14 O1 C25 177.4(2) . . . . ? 
C14 C15 O2 C26 109.4(2) . . . . ? 
C16 C15 O2 C26 -75.6(3) . . . . ? 
C17 C16 O3 C27 4.8(3) . . . . ? 
C15 C16 O3 C27 -174.8(2) . . . . ? 
  
_refine_diff_density_max    0.164 
_refine_diff_density_min   -0.143 
_refine_diff_density_rms    0.036 
  
  
  
