 
data_cu_d8v19398_0m 
  
_audit_creation_method            SHELXL-2013 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C24 H28 N2 O2' 
_chemical_formula_weight          376.48 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       triclinic 
_space_group_IT_number            1 
_space_group_name_H-M_alt         'P 1' 
_space_group_name_Hall            'P 1' 
  
_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' 
  
_cell_length_a                    5.0937(3) 
_cell_length_b                    10.1710(6) 
_cell_length_c                    10.7742(6) 
_cell_angle_alpha                 85.704(2) 
_cell_angle_beta                  77.910(2) 
_cell_angle_gamma                 89.183(2) 
_cell_volume                      544.28(5) 
_cell_formula_units_Z             1 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     9966 
_cell_measurement_theta_min       11.673 
_cell_measurement_theta_max       140.226 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.149 
_exptl_crystal_F_000              202 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.190 
_exptl_crystal_size_mid           0.120 
_exptl_crystal_size_min           0.080 
_exptl_absorpt_coefficient_mu     0.575 
_shelx_estimated_absorpt_T_min    0.899 
_shelx_estimated_absorpt_T_max    0.955 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.5589 
_exptl_absorpt_correction_T_max   0.7513 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\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             14368 
_diffrn_reflns_av_unetI/netI      0.0364 
_diffrn_reflns_av_R_equivalents   0.0425 
_diffrn_reflns_limit_h_min        -5 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          5.836 
_diffrn_reflns_theta_max          67.493 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.979 
_diffrn_measured_fraction_theta_full  0.974 
_diffrn_reflns_Laue_measured_fraction_max    0.979 
_diffrn_reflns_Laue_measured_fraction_full   0.974 
_diffrn_reflns_point_group_measured_fraction_max   0.958 
_diffrn_reflns_point_group_measured_fraction_full  0.953 
_reflns_number_total              3748 
_reflns_number_gt                 3634 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.958 
_reflns_Friedel_fraction_max      0.938 
_reflns_Friedel_fraction_full     0.933 
  
_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-2013 (Sheldrick, 2013)' 
_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)+(0.0544P)²+0.0459P] 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 
_refine_ls_extinction_coef        ? 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1710 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
; 
_refine_ls_abs_structure_Flack    -0.10(9) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          3748 
_refine_ls_number_parameters      280 
_refine_ls_number_restraints      43 
_refine_ls_R_factor_all           0.0390 
_refine_ls_R_factor_gt            0.0378 
_refine_ls_wR_factor_ref          0.1027 
_refine_ls_wR_factor_gt           0.1011 
_refine_ls_goodness_of_fit_ref    1.056 
_refine_ls_restrained_S_all       1.092 
_refine_ls_shift/su_max           0.002 
_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 
O1 O 1.0200(3) 0.6538(2) 0.43407(17) 0.0596(5) Uani 1 1 d . . . . . 
O2 O -0.0193(3) 0.3384(2) 0.5737(2) 0.0667(5) Uani 1 1 d . . . . . 
N1 N 0.5710(3) 0.62687(19) 0.47609(17) 0.0470(5) Uani 1 1 d . . . . . 
H1 H 0.4294 0.6286 0.4443 0.056 Uiso 1 1 calc R U . . . 
N2 N 0.4107(3) 0.37758(19) 0.58161(18) 0.0480(5) Uani 1 1 d . . . . . 
H2 H 0.5753 0.3544 0.5572 0.058 Uiso 1 1 calc R U . . . 
C1 C 0.8083(4) 0.6453(2) 0.3971(2) 0.0454(5) Uani 1 1 d . . . . . 
C2 C 0.8071(4) 0.6592(2) 0.2578(2) 0.0493(5) Uani 1 1 d . . . . . 
C3 C 0.6238(6) 0.5939(3) 0.2063(3) 0.0719(8) Uani 1 1 d . . . . . 
H3 H 0.4932 0.5404 0.2589 0.086 Uiso 1 1 calc R U . . . 
C4 C 0.6344(8) 0.6081(5) 0.0769(3) 0.0973(12) Uani 1 1 d . . . . . 
H4 H 0.5115 0.5630 0.0430 0.117 Uiso 1 1 calc R U . . . 
C5 C 0.8201(8) 0.6863(5) -0.0012(3) 0.0950(12) Uani 1 1 d . . . . . 
H5 H 0.8258 0.6941 -0.0882 0.114 Uiso 1 1 calc R U . . . 
C6 C 1.0001(8) 0.7540(4) 0.0483(3) 0.0926(11) Uani 1 1 d . . . . . 
H6 H 1.1239 0.8105 -0.0046 0.111 Uiso 1 1 calc R U . . . 
C7 C 0.9972(6) 0.7379(3) 0.1776(3) 0.0710(8) Uani 1 1 d . . . . . 
H7 H 1.1249 0.7808 0.2103 0.085 Uiso 1 1 calc R U . . . 
C8 C 0.2214(4) 0.3128(2) 0.5415(2) 0.0477(5) Uani 1 1 d . . . . . 
C9 C 0.3147(4) 0.2034(2) 0.4577(2) 0.0502(5) Uani 1 1 d . . . . . 
C10 C 0.1505(6) 0.0952(3) 0.4674(3) 0.0670(7) Uani 1 1 d . . . . . 
H10 H -0.0136 0.0921 0.5250 0.080 Uiso 1 1 calc R U . . . 
C11 C 0.2273(7) -0.0092(3) 0.3919(4) 0.0810(9) Uani 1 1 d . . . . . 
H11 H 0.1172 -0.0829 0.4006 0.097 Uiso 1 1 calc R U . . . 
C12 C 0.4648(7) -0.0037(3) 0.3049(4) 0.0797(9) Uani 1 1 d . . . . . 
H12 H 0.5145 -0.0727 0.2529 0.096 Uiso 1 1 calc R U . . . 
C13 C 0.6298(7) 0.1035(4) 0.2941(4) 0.0828(9) Uani 1 1 d . . . . . 
H13 H 0.7914 0.1071 0.2348 0.099 Uiso 1 1 calc R U . . . 
C14 C 0.5568(5) 0.2065(3) 0.3712(3) 0.0668(7) Uani 1 1 d . . . . . 
H14 H 0.6714 0.2782 0.3648 0.080 Uiso 1 1 calc R U . . . 
C15 C 0.5388(4) 0.6040(2) 0.6132(2) 0.0455(5) Uani 1 1 d . . . . . 
H15 H 0.7157 0.5832 0.6318 0.055 Uiso 1 1 calc R U . . . 
C16 C 0.4347(5) 0.7278(3) 0.6796(2) 0.0569(6) Uani 1 1 d . . . . . 
H16A H 0.2661 0.7532 0.6565 0.068 Uiso 1 1 calc R U . . . 
H16B H 0.3985 0.7067 0.7709 0.068 Uiso 1 1 calc R U . . . 
C17 C 0.6262(6) 0.8451(3) 0.6477(3) 0.0679(7) Uani 1 1 d . . . . . 
H17A H 0.8002 0.8177 0.6634 0.081 Uiso 1 1 calc R U . . . 
H17B H 0.6490 0.8719 0.5578 0.081 Uiso 1 1 calc R U . . . 
C18 C 0.5325(8) 0.9600(3) 0.7222(4) 0.0865(10) Uani 1 1 d . . . . . 
H18 H 0.3712 0.9985 0.7117 0.104 Uiso 1 1 calc R U . . . 
C19 C 0.6539(14) 1.0106(5) 0.7995(6) 0.139(2) Uani 1 1 d . . . . . 
H19A H 0.8159 0.9752 0.8129 0.167 Uiso 1 1 calc R U . . . 
H19B H 0.5803 1.0829 0.8423 0.167 Uiso 1 1 calc R U . . . 
C20 C 0.3521(4) 0.4854(2) 0.6645(2) 0.0470(5) Uani 1 1 d . . . . . 
H20 H 0.1664 0.5136 0.6672 0.056 Uiso 1 1 calc R U . . . 
C21 C 0.3786(6) 0.4387(3) 0.8000(3) 0.0675(7) Uani 1 1 d . . . . . 
H21A H 0.5569 0.4022 0.7962 0.081 Uiso 1 1 calc R U . . . 
H21B H 0.3637 0.5148 0.8501 0.081 Uiso 1 1 calc R U . . . 
C22 C 0.1771(9) 0.3378(5) 0.8678(4) 0.0877(10) Uani 1 1 d D . . . . 
C23 C 0.2642(19) 0.2901(11) 0.9965(9) 0.101(2) Uani 0.6 1 d D U P A 1 
H23 H 0.4142 0.2361 0.9925 0.121 Uiso 0.6 1 calc R U P A 1 
C24 C 0.1396(16) 0.3218(8) 1.1048(6) 0.1151(18) Uani 0.7 1 d D U P A 1 
H24A H -0.0110 0.3756 1.1113 0.138 Uiso 0.7 1 calc R U P A 1 
H24B H 0.1989 0.2911 1.1776 0.138 Uiso 0.7 1 calc R U P A 1 
C23' C 0.152(3) 0.3068(19) 0.9986(14) 0.107(2) Uani 0.4 1 d D U P A 2 
H23' H -0.0088 0.3374 1.0450 0.129 Uiso 0.4 1 calc R U P A 2 
C24' C 0.277(4) 0.2541(19) 1.0632(17) 0.117(3) Uani 0.3 1 d D U P A 2 
H24C H 0.4433 0.2188 1.0283 0.140 Uiso 0.3 1 calc R U P A 2 
H24D H 0.2129 0.2463 1.1508 0.140 Uiso 0.3 1 calc R U P A 2 
H22B H 0.002(12) 0.374(5) 0.869(5) 0.129(18) Uiso 1 1 d . . . . . 
H22A H 0.174(9) 0.265(5) 0.812(4) 0.098(13) 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 
O1 C1 1.232(3) . ? 
O2 C8 1.232(3) . ? 
N1 C1 1.331(3) . ? 
N1 C15 1.453(3) . ? 
N1 H1 0.8600 . ? 
N2 C8 1.336(3) . ? 
N2 C20 1.454(3) . ? 
N2 H2 0.8600 . ? 
C1 C2 1.498(3) . ? 
C2 C7 1.377(4) . ? 
C2 C3 1.382(4) . ? 
C3 C4 1.380(5) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.350(6) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.370(6) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.387(4) . ? 
C6 H6 0.9300 . ? 
C7 H7 0.9300 . ? 
C8 C9 1.495(3) . ? 
C9 C10 1.376(4) . ? 
C9 C14 1.380(3) . ? 
C10 C11 1.388(4) . ? 
C10 H10 0.9300 . ? 
C11 C12 1.365(5) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.369(5) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.385(4) . ? 
C13 H13 0.9300 . ? 
C14 H14 0.9300 . ? 
C15 C16 1.529(3) . ? 
C15 C20 1.542(3) . ? 
C15 H15 0.9800 . ? 
C16 C17 1.524(4) . ? 
C16 H16A 0.9700 . ? 
C16 H16B 0.9700 . ? 
C17 C18 1.484(4) . ? 
C17 H17A 0.9700 . ? 
C17 H17B 0.9700 . ? 
C18 C19 1.276(6) . ? 
C18 H18 0.9300 . ? 
C19 H19A 0.9300 . ? 
C19 H19B 0.9300 . ? 
C20 C21 1.533(3) . ? 
C20 H20 0.9800 . ? 
C21 C22 1.498(5) . ? 
C21 H21A 0.9700 . ? 
C21 H21B 0.9700 . ? 
C22 C23' 1.400(14) . ? 
C22 C23 1.583(10) . ? 
C22 H22B 0.96(6) . ? 
C22 H22A 0.99(5) . ? 
C23 C24 1.268(11) . ? 
C23 H23 0.9300 . ? 
C24 H24A 0.9300 . ? 
C24 H24B 0.9300 . ? 
C23' C24' 1.138(19) . ? 
C23' H23' 0.9300 . ? 
C24' H24C 0.9300 . ? 
C24' H24D 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 
C1 N1 C15 123.41(18) . . ? 
C1 N1 H1 118.3 . . ? 
C15 N1 H1 118.3 . . ? 
C8 N2 C20 123.28(17) . . ? 
C8 N2 H2 118.4 . . ? 
C20 N2 H2 118.4 . . ? 
O1 C1 N1 123.0(2) . . ? 
O1 C1 C2 120.46(19) . . ? 
N1 C1 C2 116.51(18) . . ? 
C7 C2 C3 118.6(2) . . ? 
C7 C2 C1 119.2(2) . . ? 
C3 C2 C1 122.3(2) . . ? 
C4 C3 C2 120.0(3) . . ? 
C4 C3 H3 120.0 . . ? 
C2 C3 H3 120.0 . . ? 
C5 C4 C3 121.1(4) . . ? 
C5 C4 H4 119.4 . . ? 
C3 C4 H4 119.4 . . ? 
C4 C5 C6 119.8(3) . . ? 
C4 C5 H5 120.1 . . ? 
C6 C5 H5 120.1 . . ? 
C5 C6 C7 119.8(3) . . ? 
C5 C6 H6 120.1 . . ? 
C7 C6 H6 120.1 . . ? 
C2 C7 C6 120.6(3) . . ? 
C2 C7 H7 119.7 . . ? 
C6 C7 H7 119.7 . . ? 
O2 C8 N2 122.4(2) . . ? 
O2 C8 C9 120.9(2) . . ? 
N2 C8 C9 116.66(18) . . ? 
C10 C9 C14 118.9(2) . . ? 
C10 C9 C8 118.2(2) . . ? 
C14 C9 C8 122.9(2) . . ? 
C9 C10 C11 120.6(3) . . ? 
C9 C10 H10 119.7 . . ? 
C11 C10 H10 119.7 . . ? 
C12 C11 C10 120.0(3) . . ? 
C12 C11 H11 120.0 . . ? 
C10 C11 H11 120.0 . . ? 
C11 C12 C13 120.0(3) . . ? 
C11 C12 H12 120.0 . . ? 
C13 C12 H12 120.0 . . ? 
C12 C13 C14 120.2(3) . . ? 
C12 C13 H13 119.9 . . ? 
C14 C13 H13 119.9 . . ? 
C9 C14 C13 120.3(3) . . ? 
C9 C14 H14 119.8 . . ? 
C13 C14 H14 119.8 . . ? 
N1 C15 C16 110.77(19) . . ? 
N1 C15 C20 111.02(18) . . ? 
C16 C15 C20 110.98(18) . . ? 
N1 C15 H15 108.0 . . ? 
C16 C15 H15 108.0 . . ? 
C20 C15 H15 108.0 . . ? 
C17 C16 C15 114.4(2) . . ? 
C17 C16 H16A 108.7 . . ? 
C15 C16 H16A 108.7 . . ? 
C17 C16 H16B 108.7 . . ? 
C15 C16 H16B 108.7 . . ? 
H16A C16 H16B 107.6 . . ? 
C18 C17 C16 113.5(3) . . ? 
C18 C17 H17A 108.9 . . ? 
C16 C17 H17A 108.9 . . ? 
C18 C17 H17B 108.9 . . ? 
C16 C17 H17B 108.9 . . ? 
H17A C17 H17B 107.7 . . ? 
C19 C18 C17 125.7(4) . . ? 
C19 C18 H18 117.1 . . ? 
C17 C18 H18 117.1 . . ? 
C18 C19 H19A 120.0 . . ? 
C18 C19 H19B 120.0 . . ? 
H19A C19 H19B 120.0 . . ? 
N2 C20 C21 110.2(2) . . ? 
N2 C20 C15 110.96(17) . . ? 
C21 C20 C15 110.53(19) . . ? 
N2 C20 H20 108.4 . . ? 
C21 C20 H20 108.4 . . ? 
C15 C20 H20 108.4 . . ? 
C22 C21 C20 115.5(3) . . ? 
C22 C21 H21A 108.4 . . ? 
C20 C21 H21A 108.4 . . ? 
C22 C21 H21B 108.4 . . ? 
C20 C21 H21B 108.4 . . ? 
H21A C21 H21B 107.5 . . ? 
C23' C22 C21 119.8(9) . . ? 
C21 C22 C23 107.0(5) . . ? 
C23' C22 H22B 99(3) . . ? 
C21 C22 H22B 108(3) . . ? 
C23 C22 H22B 120(3) . . ? 
C23' C22 H22A 119(3) . . ? 
C21 C22 H22A 109(3) . . ? 
C23 C22 H22A 113(3) . . ? 
H22B C22 H22A 100(4) . . ? 
C24 C23 C22 123.3(7) . . ? 
C24 C23 H23 118.4 . . ? 
C22 C23 H23 118.4 . . ? 
C23 C24 H24A 120.0 . . ? 
C23 C24 H24B 120.0 . . ? 
H24A C24 H24B 120.0 . . ? 
C24' C23' C22 136.9(17) . . ? 
C24' C23' H23' 111.5 . . ? 
C22 C23' H23' 111.5 . . ? 
C23' C24' H24C 120.0 . . ? 
C23' C24' H24D 120.0 . . ? 
H24C C24' H24D 120.0 . . ? 
  
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 
C15 N1 C1 O1 -5.3(4) . . . . ? 
C15 N1 C1 C2 176.3(2) . . . . ? 
O1 C1 C2 C7 -30.0(4) . . . . ? 
N1 C1 C2 C7 148.4(2) . . . . ? 
O1 C1 C2 C3 148.9(3) . . . . ? 
N1 C1 C2 C3 -32.6(3) . . . . ? 
C7 C2 C3 C4 0.2(5) . . . . ? 
C1 C2 C3 C4 -178.8(3) . . . . ? 
C2 C3 C4 C5 -0.7(6) . . . . ? 
C3 C4 C5 C6 -0.6(7) . . . . ? 
C4 C5 C6 C7 2.5(6) . . . . ? 
C3 C2 C7 C6 1.6(5) . . . . ? 
C1 C2 C7 C6 -179.4(3) . . . . ? 
C5 C6 C7 C2 -3.0(6) . . . . ? 
C20 N2 C8 O2 -1.2(3) . . . . ? 
C20 N2 C8 C9 -179.4(2) . . . . ? 
O2 C8 C9 C10 -31.9(3) . . . . ? 
N2 C8 C9 C10 146.3(2) . . . . ? 
O2 C8 C9 C14 147.8(3) . . . . ? 
N2 C8 C9 C14 -34.0(3) . . . . ? 
C14 C9 C10 C11 0.3(4) . . . . ? 
C8 C9 C10 C11 -179.9(3) . . . . ? 
C9 C10 C11 C12 -1.7(5) . . . . ? 
C10 C11 C12 C13 1.5(6) . . . . ? 
C11 C12 C13 C14 0.0(6) . . . . ? 
C10 C9 C14 C13 1.2(4) . . . . ? 
C8 C9 C14 C13 -178.5(3) . . . . ? 
C12 C13 C14 C9 -1.4(5) . . . . ? 
C1 N1 C15 C16 104.3(2) . . . . ? 
C1 N1 C15 C20 -132.0(2) . . . . ? 
N1 C15 C16 C17 -64.0(3) . . . . ? 
C20 C15 C16 C17 172.2(2) . . . . ? 
C15 C16 C17 C18 -174.6(3) . . . . ? 
C16 C17 C18 C19 118.1(6) . . . . ? 
C8 N2 C20 C21 105.1(2) . . . . ? 
C8 N2 C20 C15 -132.2(2) . . . . ? 
N1 C15 C20 N2 42.2(2) . . . . ? 
C16 C15 C20 N2 165.82(19) . . . . ? 
N1 C15 C20 C21 164.7(2) . . . . ? 
C16 C15 C20 C21 -71.6(2) . . . . ? 
N2 C20 C21 C22 -66.1(4) . . . . ? 
C15 C20 C21 C22 170.9(3) . . . . ? 
C20 C21 C22 C23' -168.3(8) . . . . ? 
C20 C21 C22 C23 172.5(4) . . . . ? 
C23' C22 C23 C24 -22(2) . . . . ? 
C21 C22 C23 C24 107.4(11) . . . . ? 
C21 C22 C23' C24' -70(3) . . . . ? 
C23 C22 C23' C24' -11.7(19) . . . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N2 H2 O2  0.86 2.11 2.910(2) 153.9 1_655 
N1 H1 O1  0.86 2.12 2.941(2) 158.9 1_455 
N2 H2 O2  0.86 2.11 2.910(2) 153.9 1_655 
N1 H1 O1  0.86 2.12 2.941(2) 158.9 1_455 
N2 H2 O2  0.86 2.11 2.910(2) 153.9 1_655 
N1 H1 O1  0.86 2.12 2.941(2) 158.9 1_455 
  
_refine_diff_density_max    0.135 
_refine_diff_density_min   -0.121 
_refine_diff_density_rms    0.023 
  
_shelxl_version_number 2013-4 
  
  
  
