# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2132228'
loop_
_audit_author_name
_audit_author_address
'Dr. Chao Zhou'
;Huaibei Normal University
China
;
_audit_update_record             
;
2022-01-07 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 N2'
_chemical_formula_sum            'C24 H22 N2'
_chemical_formula_weight         338.43

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'

_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                   12.796(2)
_cell_length_b                   13.651(3)
_cell_length_c                   12.334(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.073(6)
_cell_angle_gamma                90
_cell_volume                     1918.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1736
_cell_measurement_theta_min      2.9847
_cell_measurement_theta_max      27.4401

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28076
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         25.093
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3403
_reflns_number_gt                2832
_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 SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0489P)²+0.4204P] 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         3403
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.27928(12) 0.52716(10) 0.90492(13) 0.0449(3) Uani 1 1 d . . . . .
C2 C 0.26360(14) 0.42222(12) 0.92461(15) 0.0569(4) Uani 1 1 d . . . . .
C3 C 0.37143(12) 0.53469(10) 0.86531(12) 0.0427(3) Uani 1 1 d . . . . .
C4 C 0.31358(13) 0.58395(11) 1.02913(13) 0.0484(3) Uani 1 1 d . . . . .
H4 H 0.3483 0.5376 1.0971 0.058 Uiso 1 1 calc R U . . .
C5 C 0.39987(12) 0.66879(10) 1.05048(12) 0.0461(3) Uani 1 1 d . . . . .
H5 H 0.4673 0.6410 1.0438 0.055 Uiso 1 1 calc R U . . .
C6 C 0.35259(13) 0.75115(11) 0.95717(13) 0.0500(4) Uani 1 1 d . . . . .
H6A H 0.3265 0.7244 0.8761 0.060 Uiso 1 1 calc R U . . .
H6B H 0.2855 0.7811 0.9607 0.060 Uiso 1 1 calc R U . . .
C7 C 0.44616(15) 0.82853(12) 0.98114(14) 0.0609(4) Uani 1 1 d . . . . .
H7A H 0.5095 0.8000 0.9690 0.073 Uiso 1 1 calc R U . . .
H7B H 0.4126 0.8817 0.9234 0.073 Uiso 1 1 calc R U . . .
C8 C 0.49503(16) 0.86877(13) 1.10948(16) 0.0682(5) Uani 1 1 d . . . . .
H8A H 0.5580 0.9144 1.1234 0.082 Uiso 1 1 calc R U . . .
H8B H 0.4339 0.9041 1.1188 0.082 Uiso 1 1 calc R U . . .
C9 C 0.54112(15) 0.78715(14) 1.20261(15) 0.0695(5) Uani 1 1 d . . . . .
H9A H 0.5674 0.8143 1.2835 0.083 Uiso 1 1 calc R U . . .
H9B H 0.6079 0.7564 1.1992 0.083 Uiso 1 1 calc R U . . .
C10 C 0.44715(15) 0.71080(13) 1.17917(13) 0.0620(4) Uani 1 1 d . . . . .
H10A H 0.3833 0.7403 1.1894 0.074 Uiso 1 1 calc R U . . .
H10B H 0.4797 0.6582 1.2381 0.074 Uiso 1 1 calc R U . . .
C11 C 0.19361(13) 0.61379(11) 1.01246(14) 0.0524(4) Uani 1 1 d . . . . .
C12 C 0.16141(17) 0.64134(13) 1.10155(17) 0.0690(5) Uani 1 1 d . . . . .
H12 H 0.2165 0.6422 1.1832 0.083 Uiso 1 1 calc R U . . .
C13 C 0.04700(19) 0.66732(15) 1.0673(2) 0.0808(6) Uani 1 1 d . . . . .
H13 H 0.0243 0.6847 1.1264 0.097 Uiso 1 1 calc R U . . .
C14 C -0.03428(17) 0.66786(16) 0.9467(2) 0.0840(6) Uani 1 1 d . . . . .
H14 H -0.1110 0.6869 0.9253 0.101 Uiso 1 1 calc R U . . .
C15 C -0.00415(15) 0.64057(14) 0.85685(18) 0.0718(5) Uani 1 1 d . . . . .
H15 H -0.0594 0.6415 0.7753 0.086 Uiso 1 1 calc R U . . .
C16 C 0.11081(13) 0.61163(11) 0.89115(14) 0.0526(4) Uani 1 1 d . . . . .
C17 C 0.16016(12) 0.57063(10) 0.81383(13) 0.0462(3) Uani 1 1 d . . . . .
C18 C 0.11181(12) 0.57094(11) 0.69269(14) 0.0510(4) Uani 1 1 d . . . . .
H18 H 0.0414 0.6051 0.6543 0.061 Uiso 1 1 calc R U . . .
C19 C 0.15202(12) 0.52580(11) 0.60977(13) 0.0503(4) Uani 1 1 d . . . . .
C20 C 0.20298(16) 0.43361(13) 0.62944(16) 0.0682(5) Uani 1 1 d . . . . .
H20 H 0.2126 0.3980 0.6976 0.082 Uiso 1 1 calc R U . . .
C21 C 0.23961(16) 0.39382(16) 0.55007(19) 0.0805(6) Uani 1 1 d . . . . .
H21 H 0.2744 0.3322 0.5657 0.097 Uiso 1 1 calc R U . . .
C22 C 0.22543(16) 0.44345(18) 0.4497(2) 0.0823(6) Uani 1 1 d . . . . .
H22 H 0.2525 0.4170 0.3976 0.099 Uiso 1 1 calc R U . . .
C23 C 0.17068(18) 0.53365(17) 0.42449(18) 0.0811(6) Uani 1 1 d . . . . .
H23 H 0.1583 0.5671 0.3539 0.097 Uiso 1 1 calc R U . . .
C24 C 0.13412(15) 0.57444(13) 0.50473(15) 0.0637(4) Uani 1 1 d . . . . .
H24 H 0.0972 0.6352 0.4874 0.076 Uiso 1 1 calc R U . . .
N1 N 0.24950(17) 0.34242(11) 0.93932(17) 0.0864(5) Uani 1 1 d . . . . .
N2 N 0.44572(11) 0.54161(10) 0.83975(11) 0.0562(3) 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 C3 1.4711(18) . ?
C1 C2 1.482(2) . ?
C1 C17 1.542(2) . ?
C1 C4 1.590(2) . ?
C2 N1 1.132(2) . ?
C3 N2 1.1334(17) . ?
C4 C11 1.509(2) . ?
C4 C5 1.538(2) . ?
C5 C6 1.5234(19) . ?
C5 C10 1.530(2) . ?
C6 C7 1.521(2) . ?
C7 C8 1.516(2) . ?
C8 C9 1.514(3) . ?
C9 C10 1.516(2) . ?
C11 C16 1.385(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.373(3) . ?
C13 C14 1.373(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.390(2) . ?
C16 C17 1.4729(19) . ?
C17 C18 1.332(2) . ?
C18 C19 1.473(2) . ?
C19 C24 1.379(2) . ?
C19 C20 1.387(2) . ?
C20 C21 1.375(2) . ?
C21 C22 1.350(3) . ?
C22 C23 1.380(3) . ?
C23 C24 1.389(3) . ?

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
C3 C1 C2 108.11(11) . . ?
C3 C1 C17 114.01(11) . . ?
C2 C1 C17 109.19(12) . . ?
C3 C1 C4 111.99(11) . . ?
C2 C1 C4 108.18(11) . . ?
C17 C1 C4 105.20(10) . . ?
N1 C2 C1 178.69(17) . . ?
N2 C3 C1 177.05(15) . . ?
C11 C4 C5 115.25(12) . . ?
C11 C4 C1 100.53(11) . . ?
C5 C4 C1 113.19(10) . . ?
C6 C5 C10 109.92(12) . . ?
C6 C5 C4 114.78(12) . . ?
C10 C5 C4 111.96(12) . . ?
C7 C6 C5 111.03(12) . . ?
C8 C7 C6 111.63(13) . . ?
C9 C8 C7 111.03(14) . . ?
C8 C9 C10 111.09(14) . . ?
C9 C10 C5 111.12(13) . . ?
C16 C11 C12 120.24(15) . . ?
C16 C11 C4 111.83(12) . . ?
C12 C11 C4 127.93(15) . . ?
C13 C12 C11 119.01(18) . . ?
C12 C13 C14 120.73(16) . . ?
C13 C14 C15 121.16(17) . . ?
C14 C15 C16 118.42(18) . . ?
C11 C16 C15 120.38(14) . . ?
C11 C16 C17 111.40(13) . . ?
C15 C16 C17 128.11(15) . . ?
C18 C17 C16 127.44(13) . . ?
C18 C17 C1 128.23(12) . . ?
C16 C17 C1 104.32(12) . . ?
C17 C18 C19 130.31(14) . . ?
C24 C19 C20 117.71(15) . . ?
C24 C19 C18 119.33(14) . . ?
C20 C19 C18 122.90(15) . . ?
C21 C20 C19 121.29(18) . . ?
C22 C21 C20 120.5(2) . . ?
C21 C22 C23 119.77(18) . . ?
C22 C23 C24 119.90(19) . . ?
C19 C24 C23 120.70(18) . . ?

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.026

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2132227'
loop_
_audit_author_name
_audit_author_address
'Dr. Chao Zhou'
;Huaibei Normal University
China
;
_audit_update_record             
;
2022-01-07 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        cz-1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 N2'
_chemical_formula_sum            'C24 H22 N2'
_chemical_formula_weight         338.43

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'

_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                   10.1427(17)
_cell_length_b                   14.521(3)
_cell_length_c                   13.705(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.529(6)
_cell_angle_gamma                90
_cell_volume                     1962.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2289
_cell_measurement_theta_min      2.8055
_cell_measurement_theta_max      27.3613

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            81617
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.497
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3476
_reflns_number_gt                3209
_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 SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0480P)²+0.5653P] 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         3476
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.96118(15) 0.20180(10) 0.24810(11) 0.0471(4) Uani 1 1 d . . . . .
H1 H 1.0132 0.2016 0.3137 0.057 Uiso 1 1 calc R U . . .
C2 C 1.00527(17) 0.25010(11) 0.17528(13) 0.0566(4) Uani 1 1 d . . . . .
H2 H 1.0870 0.2819 0.1920 0.068 Uiso 1 1 calc R U . . .
C3 C 0.92941(19) 0.25159(12) 0.07834(14) 0.0623(5) Uani 1 1 d . . . . .
H3 H 0.9598 0.2838 0.0292 0.075 Uiso 1 1 calc R U . . .
C4 C 0.8083(2) 0.20513(12) 0.05439(12) 0.0632(5) Uani 1 1 d . . . . .
H4 H 0.7560 0.2066 -0.0111 0.076 Uiso 1 1 calc R U . . .
C5 C 0.76348(17) 0.15644(11) 0.12635(12) 0.0529(4) Uani 1 1 d . . . . .
H5 H 0.6812 0.1252 0.1092 0.064 Uiso 1 1 calc R U . . .
C6 C 0.84020(14) 0.15349(9) 0.22461(10) 0.0402(3) Uani 1 1 d . . . . .
C7 C 0.78954(14) 0.10607(10) 0.30343(10) 0.0418(3) Uani 1 1 d . . . . .
H7 H 0.7988 0.1375 0.3638 0.050 Uiso 1 1 calc R U . . .
C8 C 0.73207(13) 0.02343(9) 0.29820(9) 0.0364(3) Uani 1 1 d . . . . .
C9 C 0.71503(13) -0.05033(9) 0.22311(10) 0.0368(3) Uani 1 1 d . . . . .
C10 C 0.78807(15) -0.06730(10) 0.15080(11) 0.0453(3) Uani 1 1 d . . . . .
H10 H 0.8538 -0.0260 0.1410 0.054 Uiso 1 1 calc R U . . .
C11 C 0.76139(18) -0.14614(11) 0.09409(12) 0.0552(4) Uani 1 1 d . . . . .
H11 H 0.8103 -0.1585 0.0460 0.066 Uiso 1 1 calc R U . . .
C12 C 0.66310(19) -0.20702(11) 0.10758(13) 0.0598(4) Uani 1 1 d . . . . .
H12 H 0.6457 -0.2596 0.0679 0.072 Uiso 1 1 calc R U . . .
C13 C 0.59005(17) -0.19108(10) 0.17916(12) 0.0519(4) Uani 1 1 d . . . . .
H13 H 0.5241 -0.2326 0.1882 0.062 Uiso 1 1 calc R U . . .
C14 C 0.61664(14) -0.11238(9) 0.23724(10) 0.0391(3) Uani 1 1 d . . . . .
C15 C 0.55012(14) -0.08135(9) 0.31936(10) 0.0389(3) Uani 1 1 d . . . . .
H15 H 0.5411 -0.1340 0.3620 0.047 Uiso 1 1 calc R U . . .
C16 C 0.66228(14) -0.01396(9) 0.37882(9) 0.0382(3) Uani 1 1 d . . . . .
C17 C 0.76171(16) -0.06785(11) 0.45343(11) 0.0481(4) Uani 1 1 d . . . . .
C18 C 0.60901(14) 0.05941(10) 0.43273(10) 0.0426(3) Uani 1 1 d . . . . .
C19 C 0.41071(14) -0.03488(10) 0.28195(10) 0.0409(3) Uani 1 1 d . . . . .
H19 H 0.3850 -0.0093 0.3411 0.049 Uiso 1 1 calc R U . . .
C20 C 0.40885(14) 0.04463(10) 0.20893(11) 0.0456(3) Uani 1 1 d . . . . .
H20A H 0.4751 0.0905 0.2397 0.055 Uiso 1 1 calc R U . . .
H20B H 0.4335 0.0221 0.1490 0.055 Uiso 1 1 calc R U . . .
C21 C 0.26888(16) 0.08840(12) 0.18052(13) 0.0566(4) Uani 1 1 d . . . . .
H21A H 0.2468 0.1143 0.2400 0.068 Uiso 1 1 calc R U . . .
H21B H 0.2694 0.1382 0.1334 0.068 Uiso 1 1 calc R U . . .
C22 C 0.16205(17) 0.01865(13) 0.13383(15) 0.0657(5) Uani 1 1 d . . . . .
H22A H 0.0735 0.0477 0.1190 0.079 Uiso 1 1 calc R U . . .
H22B H 0.1795 -0.0034 0.0712 0.079 Uiso 1 1 calc R U . . .
C23 C 0.16277(17) -0.06158(13) 0.20404(17) 0.0704(5) Uani 1 1 d . . . . .
H23A H 0.0983 -0.1076 0.1709 0.085 Uiso 1 1 calc R U . . .
H23B H 0.1342 -0.0405 0.2631 0.085 Uiso 1 1 calc R U . . .
C24 C 0.30294(16) -0.10522(11) 0.23618(14) 0.0580(4) Uani 1 1 d . . . . .
H24A H 0.3009 -0.1534 0.2848 0.070 Uiso 1 1 calc R U . . .
H24B H 0.3264 -0.1333 0.1783 0.070 Uiso 1 1 calc R U . . .
N1 N 0.83720(17) -0.11043(13) 0.50954(12) 0.0757(5) Uani 1 1 d . . . . .
N2 N 0.56712(15) 0.11612(10) 0.47391(10) 0.0598(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(2) . ?
C1 C6 1.3844(19) . ?
C2 C3 1.371(3) . ?
C3 C4 1.373(2) . ?
C4 C5 1.374(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.4713(19) . ?
C7 C8 1.329(2) . ?
C8 C9 1.4673(18) . ?
C8 C16 1.5435(18) . ?
C9 C14 1.3913(19) . ?
C9 C10 1.3912(19) . ?
C10 C11 1.375(2) . ?
C11 C12 1.377(2) . ?
C12 C13 1.380(2) . ?
C13 C14 1.383(2) . ?
C14 C15 1.5100(19) . ?
C15 C19 1.5422(19) . ?
C15 C16 1.5755(19) . ?
C16 C18 1.470(2) . ?
C16 C17 1.481(2) . ?
C17 N1 1.133(2) . ?
C18 N2 1.1356(19) . ?
C19 C24 1.520(2) . ?
C19 C20 1.5251(19) . ?
C20 C21 1.521(2) . ?
C21 C22 1.512(2) . ?
C22 C23 1.510(3) . ?
C23 C24 1.524(2) . ?

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 120.66(14) . . ?
C3 C2 C1 120.44(15) . . ?
C4 C3 C2 119.47(15) . . ?
C3 C4 C5 120.60(16) . . ?
C4 C5 C6 120.48(15) . . ?
C1 C6 C5 118.33(13) . . ?
C1 C6 C7 120.62(13) . . ?
C5 C6 C7 120.89(13) . . ?
C8 C7 C6 127.39(13) . . ?
C7 C8 C9 132.48(12) . . ?
C7 C8 C16 123.23(12) . . ?
C9 C8 C16 104.29(11) . . ?
C14 C9 C10 120.22(13) . . ?
C14 C9 C8 110.23(11) . . ?
C10 C9 C8 129.35(13) . . ?
C11 C10 C9 118.89(14) . . ?
C12 C11 C10 120.79(14) . . ?
C11 C12 C13 120.90(15) . . ?
C14 C13 C12 118.88(15) . . ?
C13 C14 C9 120.32(13) . . ?
C13 C14 C15 127.93(13) . . ?
C9 C14 C15 111.75(11) . . ?
C14 C15 C19 114.68(11) . . ?
C14 C15 C16 100.16(10) . . ?
C19 C15 C16 113.27(11) . . ?
C18 C16 C17 107.88(11) . . ?
C18 C16 C8 112.89(11) . . ?
C17 C16 C8 109.14(11) . . ?
C18 C16 C15 113.86(11) . . ?
C17 C16 C15 108.76(11) . . ?
C8 C16 C15 104.17(10) . . ?
N1 C17 C16 178.80(19) . . ?
N2 C18 C16 179.56(17) . . ?
C24 C19 C20 109.91(12) . . ?
C24 C19 C15 110.98(12) . . ?
C20 C19 C15 114.77(11) . . ?
C21 C20 C19 110.61(12) . . ?
C22 C21 C20 111.22(14) . . ?
C23 C22 C21 110.55(14) . . ?
C22 C23 C24 111.71(14) . . ?
C19 C24 C23 111.84(14) . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.033

_shelxl_version_number           2014-3

