 
data_1_a
 
_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       triclinic
_space_group_IT_number            2
_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'
 '-x, -y, -z'
 
_cell_length_a                    7.326(2)
_cell_length_b                    9.882(3)
_cell_length_c                    13.685(4)
_cell_angle_alpha                 106.563(4)
_cell_angle_beta                  92.469(4)
_cell_angle_gamma                 107.893(4)
_cell_volume                      894.4(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     273(2)
_cell_measurement_reflns_used     2688
_cell_measurement_theta_min       2.95
_cell_measurement_theta_max       29.77
 
_exptl_crystal_description        block
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.312          
_exptl_crystal_F_000              372
_exptl_transmission_factor_min    0.864
_exptl_transmission_factor_max    0.864
_exptl_crystal_size_max           0.220
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.180
_exptl_absorpt_coefficient_mu     0.083
_shelx_estimated_absorpt_T_min    0.982
_shelx_estimated_absorpt_T_max    0.985
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    sadabs
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       273(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   CCD
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9083
_diffrn_reflns_av_unetI/netI      0.0472
_diffrn_reflns_av_R_equivalents   0.0247
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          1.569
_diffrn_reflns_theta_max          30.283
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.965
_diffrn_measured_fraction_theta_full  0.987
_diffrn_reflns_Laue_measured_fraction_max    0.965
_diffrn_reflns_Laue_measured_fraction_full   0.987
_diffrn_reflns_point_group_measured_fraction_max   0.965
_diffrn_reflns_point_group_measured_fraction_full  0.987
_reflns_number_total              5172
_reflns_number_gt                 3509
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_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)+(0.1170P)²+0.0015P] 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      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5172
_refine_ls_number_parameters      246
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0847
_refine_ls_R_factor_gt            0.0562
_refine_ls_wR_factor_ref          0.1914
_refine_ls_wR_factor_gt           0.1676
_refine_ls_goodness_of_fit_ref    1.033
_refine_ls_restrained_S_all       1.034
_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 0.2846(3) 0.3781(2) 0.58548(18) 0.0569(5) Uani 1 1 d . . . . .
H1A H 0.3182 0.3073 0.5315 0.085 Uiso 1 1 calc R U . . .
H1B H 0.1605 0.3300 0.6024 0.085 Uiso 1 1 calc R U . . .
H1C H 0.3808 0.4148 0.6453 0.085 Uiso 1 1 calc R U . . .
C2 C 0.2758(3) 0.5063(2) 0.54986(14) 0.0407(4) Uani 1 1 d . . . . .
C3 C 0.2117(3) 0.48377(19) 0.44848(14) 0.0415(4) Uani 1 1 d . . . . .
H3 H 0.1736 0.3875 0.4019 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2025(2) 0.60007(18) 0.41426(12) 0.0363(4) Uani 1 1 d . . . . .
H4 H 0.1601 0.5817 0.3452 0.044 Uiso 1 1 calc R U . . .
C5 C 0.2560(2) 0.74444(17) 0.48221(11) 0.0318(3) Uani 1 1 d . . . . .
C6 C 0.3174(3) 0.76814(19) 0.58496(12) 0.0386(4) Uani 1 1 d . . . . .
H6 H 0.3510 0.8637 0.6321 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3288(3) 0.6509(2) 0.61737(13) 0.0446(4) Uani 1 1 d . . . . .
H7 H 0.3731 0.6691 0.6862 0.053 Uiso 1 1 calc R U . . .
C8 C 0.2430(2) 0.87319(18) 0.44992(11) 0.0334(3) Uani 1 1 d . . . . .
C9 C 0.2900(2) 0.87384(17) 0.34732(11) 0.0323(3) Uani 1 1 d . . . . .
C10 C 0.4134(2) 0.81157(17) 0.29261(11) 0.0330(3) Uani 1 1 d . . . . .
H10 H 0.4708 0.7492 0.3115 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4399(2) 0.85576(17) 0.20459(11) 0.0316(3) Uani 1 1 d . . . . .
C12 C 0.3265(2) 0.94870(15) 0.20543(10) 0.0277(3) Uani 1 1 d . U . . .
C13 C 0.2897(3) 1.02022(18) 0.13647(13) 0.0379(4) Uani 1 1 d . . . . .
H13 H 0.3517 1.0158 0.0783 0.045 Uiso 1 1 calc R U . . .
C14 C 0.1633(3) 1.09589(19) 0.15472(14) 0.0437(4) Uani 1 1 d . . . . .
H14 H 0.1384 1.1437 0.1088 0.052 Uiso 1 1 calc R U . . .
C15 C 0.0685(3) 1.1033(2) 0.24274(14) 0.0446(4) Uani 1 1 d . . . . .
H15 H -0.0192 1.1551 0.2541 0.054 Uiso 1 1 calc R U . . .
C16 C 0.1051(3) 1.03520(19) 0.31070(13) 0.0391(4) Uani 1 1 d . . . . .
H16 H 0.0431 1.0401 0.3689 0.047 Uiso 1 1 calc R U . . .
C17 C 0.5663(2) 0.82206(17) 0.12961(11) 0.0333(3) Uani 1 1 d . . . . .
C18 C 0.6356(2) 0.69407(17) 0.12670(11) 0.0319(3) Uani 1 1 d . . . . .
C19 C 0.5138(2) 0.55897(18) 0.13298(12) 0.0364(4) Uani 1 1 d . . . . .
H19 H 0.3851 0.5472 0.1413 0.044 Uiso 1 1 calc R U . . .
C20 C 0.5824(3) 0.44223(19) 0.12696(12) 0.0412(4) Uani 1 1 d . . . . .
H20 H 0.4977 0.3516 0.1292 0.049 Uiso 1 1 calc R U . . .
C21 C 0.7735(3) 0.4563(2) 0.11762(13) 0.0425(4) Uani 1 1 d . . . . .
C22 C 0.8953(3) 0.5917(2) 0.11061(15) 0.0465(4) Uani 1 1 d . . . . .
H22 H 1.0249 0.6041 0.1043 0.056 Uiso 1 1 calc R U . . .
C23 C 0.8265(2) 0.70729(19) 0.11293(13) 0.0405(4) Uani 1 1 d . . . . .
H23 H 0.9087 0.7952 0.1052 0.049 Uiso 1 1 calc R U . . .
C24 C 0.8503(4) 0.3307(3) 0.1147(2) 0.0667(6) Uani 1 1 d . . . . .
H24A H 0.9254 0.3522 0.1799 0.100 Uiso 1 1 calc R U . . .
H24B H 0.9306 0.3208 0.0613 0.100 Uiso 1 1 calc R U . . .
H24C H 0.7439 0.2389 0.1011 0.100 Uiso 1 1 calc R U . . .
N1 N 0.2346(2) 0.95888(15) 0.29280(10) 0.0343(3) Uani 1 1 d . U . . .
O1 O 0.1982(2) 0.97323(15) 0.50700(9) 0.0511(4) Uani 1 1 d . . . . .
O2 O 0.6204(2) 0.89630(15) 0.07170(10) 0.0506(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 1.499(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.378(3) . ?
C2 C7 1.386(3) . ?
C3 C4 1.377(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(2) . ?
C5 C8 1.488(2) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.2154(19) . ?
C8 C9 1.461(2) . ?
C9 C10 1.376(2) . ?
C9 N1 1.4029(18) . ?
C10 C11 1.3954(19) . ?
C10 H10 0.9300 . ?
C11 C12 1.413(2) . ?
C11 C17 1.448(2) . ?
C12 N1 1.3911(18) . ?
C12 C13 1.3921(19) . ?
C13 C14 1.348(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.411(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.355(2) . ?
C15 H15 0.9300 . ?
C16 N1 1.372(2) . ?
C16 H16 0.9300 . ?
C17 O2 1.2261(17) . ?
C17 C18 1.492(2) . ?
C18 C19 1.388(2) . ?
C18 C23 1.390(2) . ?
C19 C20 1.377(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(3) . ?
C21 C24 1.504(3) . ?
C22 C23 1.377(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.58(15) . . ?
C3 C2 C1 120.84(18) . . ?
C7 C2 C1 121.57(17) . . ?
C4 C3 C2 121.72(17) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.38(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 118.44(14) . . ?
C4 C5 C8 122.53(14) . . ?
C6 C5 C8 118.99(15) . . ?
C7 C6 C5 120.33(16) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 121.53(16) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
O1 C8 C9 122.13(14) . . ?
O1 C8 C5 121.29(13) . . ?
C9 C8 C5 116.57(13) . . ?
C10 C9 N1 107.20(12) . . ?
C10 C9 C8 128.15(14) . . ?
N1 C9 C8 124.11(14) . . ?
C9 C10 C11 110.06(13) . . ?
C9 C10 H10 125.0 . . ?
C11 C10 H10 125.0 . . ?
C10 C11 C12 106.31(13) . . ?
C10 C11 C17 127.69(14) . . ?
C12 C11 C17 125.91(13) . . ?
N1 C12 C13 119.34(14) . . ?
N1 C12 C11 108.09(12) . . ?
C13 C12 C11 132.52(14) . . ?
C14 C13 C12 119.40(15) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.75(14) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.14(16) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 N1 119.31(15) . . ?
C15 C16 H16 120.3 . . ?
N1 C16 H16 120.3 . . ?
O2 C17 C11 122.58(15) . . ?
O2 C17 C18 120.00(14) . . ?
C11 C17 C18 117.40(12) . . ?
C19 C18 C23 118.35(14) . . ?
C19 C18 C17 122.28(14) . . ?
C23 C18 C17 119.32(14) . . ?
C20 C19 C18 120.39(16) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 121.70(16) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C22 117.81(16) . . ?
C20 C21 C24 121.77(18) . . ?
C22 C21 C24 120.41(18) . . ?
C23 C22 C21 120.91(17) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C18 120.74(15) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 N1 C12 121.04(13) . . ?
C16 N1 C9 130.50(13) . . ?
C12 N1 C9 108.34(12) . . ?
 
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
C7 C2 C3 C4 0.9(3) . . . . ?
C1 C2 C3 C4 179.98(17) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C3 C4 C5 C8 -178.08(15) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C8 C5 C6 C7 179.29(16) . . . . ?
C5 C6 C7 C2 -1.5(3) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C1 C2 C7 C6 -178.82(18) . . . . ?
C4 C5 C8 O1 144.04(18) . . . . ?
C6 C5 C8 O1 -33.6(2) . . . . ?
C4 C5 C8 C9 -36.9(2) . . . . ?
C6 C5 C8 C9 145.39(15) . . . . ?
O1 C8 C9 C10 150.62(18) . . . . ?
C5 C8 C9 C10 -28.4(2) . . . . ?
O1 C8 C9 N1 -19.9(3) . . . . ?
C5 C8 C9 N1 161.09(15) . . . . ?
N1 C9 C10 C11 0.51(19) . . . . ?
C8 C9 C10 C11 -171.27(16) . . . . ?
C9 C10 C11 C12 -0.31(18) . . . . ?
C9 C10 C11 C17 176.32(16) . . . . ?
C10 C11 C12 N1 -0.01(18) . . . . ?
C17 C11 C12 N1 -176.72(15) . . . . ?
C10 C11 C12 C13 -177.23(16) . . . . ?
C17 C11 C12 C13 6.1(3) . . . . ?
N1 C12 C13 C14 -1.1(2) . . . . ?
C11 C12 C13 C14 175.85(17) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 N1 -0.2(3) . . . . ?
C10 C11 C17 O2 -159.62(17) . . . . ?
C12 C11 C17 O2 16.4(3) . . . . ?
C10 C11 C17 C18 18.5(2) . . . . ?
C12 C11 C17 C18 -165.47(14) . . . . ?
O2 C17 C18 C19 -138.62(17) . . . . ?
C11 C17 C18 C19 43.2(2) . . . . ?
O2 C17 C18 C23 38.6(2) . . . . ?
C11 C17 C18 C23 -139.58(16) . . . . ?
C23 C18 C19 C20 0.8(2) . . . . ?
C17 C18 C19 C20 178.08(14) . . . . ?
C18 C19 C20 C21 1.9(2) . . . . ?
C19 C20 C21 C22 -2.3(2) . . . . ?
C19 C20 C21 C24 177.84(18) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C24 C21 C22 C23 179.85(18) . . . . ?
C21 C22 C23 C18 2.7(3) . . . . ?
C19 C18 C23 C22 -3.1(2) . . . . ?
C17 C18 C23 C22 179.55(16) . . . . ?
C15 C16 N1 C12 -0.9(2) . . . . ?
C15 C16 N1 C9 -176.43(16) . . . . ?
C13 C12 N1 C16 1.6(2) . . . . ?
C11 C12 N1 C16 -176.08(14) . . . . ?
C13 C12 N1 C9 177.96(13) . . . . ?
C11 C12 N1 C9 0.32(18) . . . . ?
C10 C9 N1 C16 175.43(17) . . . . ?
C8 C9 N1 C16 -12.4(3) . . . . ?
C10 C9 N1 C12 -0.51(18) . . . . ?
C8 C9 N1 C12 171.69(15) . . . . ?
 
_refine_diff_density_max    0.386
_refine_diff_density_min   -0.274
_refine_diff_density_rms    0.054



