# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_p2
_database_code_depnum_ccdc_archive 'CCDC 2340063'
_audit_update_record             
;
2024-03-13 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C23 H16 Cl2 N O'
_chemical_formula_sum            'C23 H16 Cl2 N O'
_chemical_formula_weight         393.27

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'
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           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                   8.1897(5)
_cell_length_b                   29.5212(16)
_cell_length_c                   8.0550(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.460(6)
_cell_angle_gamma                90
_cell_volume                     1921.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3751
_cell_measurement_theta_min      3.359
_cell_measurement_theta_max      26.10

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.350
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11529
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.359
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3751
_reflns_number_gt                2474
_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 (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)+(0.1299P)²+1.2193P] 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
_refine_ls_extinction_coef       0.004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3751
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2665
_refine_ls_wR_factor_gt          0.2427
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.6376(7) 0.22200(14) 0.2855(6) 0.0823(14) Uani 1 1 d . . . . .
H1 H 0.7167 0.2387 0.2413 0.099 Uiso 1 1 calc R U . . .
C2 C 0.4765(8) 0.22150(16) 0.2063(6) 0.0903(16) Uani 1 1 d . . . . .
H2 H 0.4463 0.2384 0.1087 0.108 Uiso 1 1 calc R U . . .
C3 C 0.3558(6) 0.19592(15) 0.2699(6) 0.0785(12) Uani 1 1 d . . . . .
H3 H 0.2468 0.1964 0.2146 0.094 Uiso 1 1 calc R U . . .
C4 C 0.3972(5) 0.17016(13) 0.4131(5) 0.0636(10) Uani 1 1 d . . . . .
H4 H 0.3184 0.1528 0.4548 0.076 Uiso 1 1 calc R U . . .
C5 C 0.5604(5) 0.17106(11) 0.4927(5) 0.0564(9) Uani 1 1 d . . . . .
C6 C 0.6816(5) 0.19730(11) 0.4325(5) 0.0646(11) Uani 1 1 d . . . . .
C7 C 0.8335(5) 0.19251(12) 0.5498(5) 0.0638(10) Uani 1 1 d . . . . .
C8 C 0.9947(6) 0.20987(15) 0.5595(7) 0.0818(14) Uani 1 1 d . . . . .
H8 H 1.0201 0.2296 0.4773 0.098 Uiso 1 1 calc R U . . .
C9 C 1.1129(6) 0.19755(17) 0.6903(8) 0.0890(15) Uani 1 1 d . . . . .
H9 H 1.2199 0.2086 0.6954 0.107 Uiso 1 1 calc R U . . .
C10 C 1.0779(5) 0.16869(15) 0.8174(7) 0.0818(13) Uani 1 1 d . . . . .
H10 H 1.1612 0.1611 0.9061 0.098 Uiso 1 1 calc R U . . .
C11 C 0.9206(5) 0.15129(14) 0.8120(6) 0.0668(10) Uani 1 1 d . . . . .
H11 H 0.8964 0.1319 0.8958 0.080 Uiso 1 1 calc R U . . .
C12 C 0.8001(4) 0.16350(11) 0.6785(5) 0.0579(9) Uani 1 1 d . . . . .
C13 C 0.5517(4) 0.12263(10) 0.7493(4) 0.0485(8) Uani 1 1 d . . . . .
C14 C 0.5658(4) 0.13372(12) 0.9185(5) 0.0564(9) Uani 1 1 d . . . . .
H14 H 0.6251 0.1593 0.9596 0.068 Uiso 1 1 calc R U . . .
C15 C 0.4934(4) 0.10737(12) 1.0250(5) 0.0559(9) Uani 1 1 d . . . . .
H15 H 0.5071 0.1145 1.1389 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3988(4) 0.06966(11) 0.9642(4) 0.0508(8) Uani 1 1 d . . . . .
C17 C 0.3837(4) 0.05893(12) 0.7946(4) 0.0551(9) Uani 1 1 d . . . . .
H17 H 0.3199 0.0342 0.7523 0.066 Uiso 1 1 calc R U . . .
C18 C 0.4625(4) 0.08460(11) 0.6877(4) 0.0539(8) Uani 1 1 d . . . . .
H18 H 0.4556 0.0764 0.5753 0.065 Uiso 1 1 calc R U . . .
C19 C 0.3204(5) 0.04282(12) 1.0879(5) 0.0593(9) Uani 1 1 d . . . . .
C20 C 0.1569(4) 0.01994(11) 1.0347(4) 0.0506(8) Uani 1 1 d . . . . .
C21 C 0.0384(4) 0.03642(12) 0.9064(5) 0.0567(9) Uani 1 1 d . . . . .
H21 H 0.0638 0.0609 0.8426 0.068 Uiso 1 1 calc R U . . .
C22 C 0.1164(4) -0.01716(12) 1.1279(5) 0.0585(9) Uani 1 1 d . . . . .
H22 H 0.1948 -0.0289 1.2138 0.070 Uiso 1 1 calc R U . . .
C23 C 1.0033(9) 0.0794(3) 0.4164(9) 0.155(3) Uani 1 1 d . . . . .
H23A H 1.0831 0.0559 0.4039 0.186 Uiso 1 1 calc R U . . .
H23B H 1.0399 0.0949 0.5221 0.186 Uiso 1 1 calc R U . . .
N1 N 0.6331(3) 0.15009(10) 0.6427(4) 0.0542(7) Uani 1 1 d . . . . .
O1 O 0.3863(4) 0.04094(12) 1.2352(4) 0.0877(10) Uani 1 1 d . . . . .
Cl1 Cl 0.9917(3) 0.11884(6) 0.2458(2) 0.1303(7) Uani 1 1 d . . . . .
Cl2 Cl 0.8112(3) 0.05546(8) 0.4179(3) 0.1637(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 1.368(7) . ?
C1 C6 1.387(6) . ?
C2 C3 1.406(7) . ?
C3 C4 1.377(6) . ?
C4 C5 1.384(6) . ?
C5 N1 1.401(5) . ?
C5 C6 1.407(5) . ?
C6 C7 1.440(6) . ?
C7 C12 1.406(5) . ?
C7 C8 1.407(6) . ?
C8 C9 1.358(7) . ?
C9 C10 1.397(7) . ?
C10 C11 1.382(5) . ?
C11 C12 1.382(6) . ?
C12 N1 1.407(4) . ?
C13 C18 1.386(5) . ?
C13 C14 1.388(5) . ?
C13 N1 1.424(4) . ?
C14 C15 1.364(5) . ?
C15 C16 1.398(5) . ?
C16 C17 1.388(5) . ?
C16 C19 1.498(5) . ?
C17 C18 1.383(5) . ?
C19 O1 1.222(5) . ?
C19 C20 1.498(5) . ?
C20 C21 1.384(5) . ?
C20 C22 1.398(5) . ?
C21 C22 1.375(5) 3_557 ?
C22 C21 1.375(5) 3_557 ?
C23 Cl2 1.727(8) . ?
C23 Cl1 1.791(10) . ?

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 119.2(4) . . ?
C1 C2 C3 121.2(4) . . ?
C4 C3 C2 120.7(5) . . ?
C3 C4 C5 117.6(4) . . ?
C4 C5 N1 129.2(3) . . ?
C4 C5 C6 122.2(4) . . ?
N1 C5 C6 108.5(3) . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 133.4(4) . . ?
C5 C6 C7 107.6(3) . . ?
C12 C7 C8 118.4(4) . . ?
C12 C7 C6 107.0(3) . . ?
C8 C7 C6 134.6(4) . . ?
C9 C8 C7 119.2(4) . . ?
C8 C9 C10 121.8(4) . . ?
C11 C10 C9 120.4(5) . . ?
C10 C11 C12 118.0(4) . . ?
C11 C12 C7 122.2(4) . . ?
C11 C12 N1 129.1(3) . . ?
C7 C12 N1 108.7(3) . . ?
C18 C13 C14 119.8(3) . . ?
C18 C13 N1 121.1(3) . . ?
C14 C13 N1 119.1(3) . . ?
C15 C14 C13 120.6(3) . . ?
C14 C15 C16 120.5(3) . . ?
C17 C16 C15 118.8(3) . . ?
C17 C16 C19 123.7(3) . . ?
C15 C16 C19 117.5(3) . . ?
C18 C17 C16 120.8(3) . . ?
C17 C18 C13 119.5(3) . . ?
O1 C19 C16 120.1(3) . . ?
O1 C19 C20 119.3(3) . . ?
C16 C19 C20 120.6(3) . . ?
C21 C20 C22 118.5(3) . . ?
C21 C20 C19 122.6(3) . . ?
C22 C20 C19 118.6(3) . . ?
C22 C21 C20 121.0(3) 3_557 . ?
C21 C22 C20 120.5(3) 3_557 . ?
Cl2 C23 Cl1 109.8(4) . . ?
C5 N1 C12 108.3(3) . . ?
C5 N1 C13 126.6(3) . . ?
C12 N1 C13 124.9(3) . . ?

_refine_diff_density_max         0.702
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.059

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_P2
_database_code_depnum_ccdc_archive 'CCDC 2340064'
_audit_update_record             
;
2024-03-13 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C22 H14 N O'
_chemical_formula_sum            'C22 H14 N O'
_chemical_formula_weight         308.34

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                   10.3584(6)
_cell_length_b                   14.3225(7)
_cell_length_c                   10.9878(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.787(7)
_cell_angle_gamma                90
_cell_volume                     1533.88(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3724
_cell_measurement_theta_min      3.240
_cell_measurement_theta_max      26.52

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10352
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.530
_diffrn_reflns_theta_max         29.527
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3724
_reflns_number_gt                2457
_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 (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)+(0.0446P)²+0.4168P] 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         3724
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.1989(2) 0.01305(15) 0.8761(2) 0.0551(5) Uani 1 1 d . . . . .
H1 H 0.1238 0.0264 0.9013 0.080 Uiso 1 1 calc R U . . .
C2 C 0.2596(2) -0.07300(16) 0.8995(2) 0.0617(6) Uani 1 1 d . . . . .
H2 H 0.2254 -0.1185 0.9408 0.080 Uiso 1 1 calc R U . . .
C3 C 0.3718(2) -0.09310(15) 0.8620(2) 0.0627(6) Uani 1 1 d . . . . .
H3 H 0.4116 -0.1520 0.8791 0.080 Uiso 1 1 calc R U . . .
C4 C 0.4257(2) -0.02837(14) 0.8003(2) 0.0548(5) Uani 1 1 d . . . . .
H4 H 0.5008 -0.0426 0.7754 0.080 Uiso 1 1 calc R U . . .
C5 C 0.36451(18) 0.05881(12) 0.77630(17) 0.0432(4) Uani 1 1 d . . . . .
C6 C 0.25153(18) 0.08083(13) 0.81384(18) 0.0445(4) Uani 1 1 d . . . . .
C7 C 0.20982(17) 0.17443(13) 0.76944(17) 0.0435(4) Uani 1 1 d . . . . .
C8 C 0.10570(19) 0.23265(15) 0.77665(19) 0.0529(5) Uani 1 1 d . . . . .
H8 H 0.0459 0.2130 0.8184 0.080 Uiso 1 1 calc R U . . .
C9 C 0.0921(2) 0.31994(16) 0.7211(2) 0.0617(6) Uani 1 1 d . . . . .
H9 H 0.0216 0.3590 0.7243 0.080 Uiso 1 1 calc R U . . .
C10 C 0.1825(2) 0.35044(15) 0.6602(2) 0.0602(6) Uani 1 1 d . . . . .
H10 H 0.1728 0.4104 0.6257 0.080 Uiso 1 1 calc R U . . .
C11 C 0.2859(2) 0.29401(13) 0.6498(2) 0.0508(5) Uani 1 1 d . . . . .
H11 H 0.3451 0.3143 0.6078 0.080 Uiso 1 1 calc R U . . .
C12 C 0.29823(17) 0.20576(12) 0.70439(18) 0.0419(4) Uani 1 1 d . . . . .
C13 C 0.49682(17) 0.13824(12) 0.65201(18) 0.0412(4) Uani 1 1 d . . . . .
C14 C 0.62985(18) 0.11200(14) 0.72404(18) 0.0480(5) Uani 1 1 d . . . . .
H14 H 0.6508 0.0937 0.8098 0.080 Uiso 1 1 calc R U . . .
C15 C 0.73106(18) 0.11313(13) 0.66824(19) 0.0485(5) Uani 1 1 d . . . . .
H15 H 0.8188 0.0923 0.7153 0.080 Uiso 1 1 calc R U . . .
C16 C 0.70299(17) 0.14506(12) 0.54248(18) 0.0424(4) Uani 1 1 d . . . . .
C17 C 0.57045(18) 0.17335(12) 0.47243(19) 0.0448(4) Uani 1 1 d . . . . .
H17 H 0.5510 0.1964 0.3890 0.080 Uiso 1 1 calc R U . . .
C18 C 0.46693(18) 0.16772(12) 0.52504(18) 0.0440(4) Uani 1 1 d . . . . .
H18 H 0.3775 0.1836 0.4755 0.080 Uiso 1 1 calc R U . . .
C19 C 0.81322(18) 0.15311(13) 0.48367(18) 0.0443(4) Uani 1 1 d . . . . .
C20 C 0.90981(16) 0.07329(12) 0.49599(16) 0.0381(4) Uani 1 1 d . . . . .
C21 C 1.03629(17) 0.09040(12) 0.48198(17) 0.0415(4) Uani 1 1 d . . . . .
H21 H 1.0612 0.1512 0.4703 0.080 Uiso 1 1 calc R U . . .
C22 C 0.87513(17) -0.01807(12) 0.51476(18) 0.0429(4) Uani 1 1 d . . . . .
H22 H 0.7913 -0.0304 0.5252 0.080 Uiso 1 1 calc R U . . .
N1 N 0.39299(14) 0.13489(10) 0.70943(15) 0.0443(4) Uani 1 1 d . . . . .
O1 O 0.82252(15) 0.22322(10) 0.42507(15) 0.0646(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 1.368(3) . ?
C1 C6 1.400(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.400(2) . ?
C5 C6 1.402(2) . ?
C6 C7 1.442(3) . ?
C7 C8 1.387(2) . ?
C7 C12 1.412(2) . ?
C8 C9 1.377(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 N1 1.400(2) . ?
C13 C18 1.388(3) . ?
C13 C14 1.389(2) . ?
C13 N1 1.420(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(2) . ?
C16 C19 1.495(2) . ?
C17 C18 1.382(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O1 1.214(2) . ?
C19 C20 1.495(2) . ?
C20 C22 1.391(2) . ?
C20 C21 1.392(2) . ?
C21 C22 1.376(2) 3_756 ?
C21 H21 0.9300 . ?
C22 C21 1.376(2) 3_756 ?
C22 H22 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 119.10(18) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C1 C2 C3 120.60(19) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 117.79(18) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C4 C5 N1 129.59(16) . . ?
C4 C5 C6 121.38(17) . . ?
N1 C5 C6 108.93(15) . . ?
C1 C6 C5 119.31(17) . . ?
C1 C6 C7 133.51(17) . . ?
C5 C6 C7 107.09(15) . . ?
C8 C7 C12 119.21(18) . . ?
C8 C7 C6 133.60(17) . . ?
C12 C7 C6 107.17(15) . . ?
C9 C8 C7 119.03(18) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 120.87(18) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 117.36(18) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C11 C12 N1 129.70(16) . . ?
C11 C12 C7 121.88(16) . . ?
N1 C12 C7 108.41(15) . . ?
C18 C13 C14 119.72(16) . . ?
C18 C13 N1 120.79(16) . . ?
C14 C13 N1 119.49(17) . . ?
C15 C14 C13 119.96(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.67(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.84(16) . . ?
C17 C16 C19 119.65(17) . . ?
C15 C16 C19 121.46(16) . . ?
C18 C17 C16 120.86(18) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 119.82(16) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
O1 C19 C16 120.16(16) . . ?
O1 C19 C20 120.64(16) . . ?
C16 C19 C20 119.19(16) . . ?
C22 C20 C21 118.82(15) . . ?
C22 C20 C19 122.31(15) . . ?
C21 C20 C19 118.80(15) . . ?
C22 C21 C20 120.59(16) 3_756 . ?
C22 C21 H21 119.7 3_756 . ?
C20 C21 H21 119.7 . . ?
C21 C22 C20 120.58(15) 3_756 . ?
C21 C22 H22 119.7 3_756 . ?
C20 C22 H22 119.7 . . ?
C12 N1 C5 108.38(14) . . ?
C12 N1 C13 125.75(15) . . ?
C5 N1 C13 125.82(14) . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-1

