# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Compound3e
_database_code_depnum_ccdc_archive 'CCDC 2056479'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H26 N2'
_chemical_formula_sum            'C23 H26 N2'
_chemical_formula_weight         330.46

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.1551(3)
_cell_length_b                   9.5932(3)
_cell_length_c                   13.3690(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1815.41(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2751
_cell_measurement_theta_min      5.5630
_cell_measurement_theta_max      71.7870

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.536
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            5174
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.571
_diffrn_reflns_theta_max         69.987
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1713
_reflns_number_gt                1462
_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1106P)²+0.9698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1713
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1860
_refine_ls_wR_factor_gt          0.1793
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
N1 N 0.45484(11) 0.33055(17) 0.49505(12) 0.0285(4) Uani 1 1 d . . . . .
C1 C 0.50441(14) 0.23843(19) 0.43475(15) 0.0285(5) Uani 1 1 d . . . . .
C2 C 0.46926(13) 0.24272(19) 0.33925(14) 0.0273(5) Uani 1 1 d . . . . .
C3 C 0.39338(13) 0.34229(19) 0.33990(14) 0.0266(5) Uani 1 1 d . . . . .
C4 C 0.33101(14) 0.3925(2) 0.26673(16) 0.0332(5) Uani 1 1 d . . . . .
H4A H 0.334389 0.359403 0.199851 0.040 Uiso 1 1 calc R U . . .
C5 C 0.26443(15) 0.4912(2) 0.29389(17) 0.0384(6) Uani 1 1 d . . . . .
H5A H 0.222374 0.526482 0.244646 0.046 Uiso 1 1 calc R U . . .
C6 C 0.25769(15) 0.5400(2) 0.39194(17) 0.0382(5) Uani 1 1 d . . . . .
H6A H 0.211298 0.607948 0.408147 0.046 Uiso 1 1 calc R U . . .
C7 C 0.31745(14) 0.4912(2) 0.46594(16) 0.0329(5) Uani 1 1 d . . . . .
H7A H 0.312256 0.523043 0.533000 0.040 Uiso 1 1 calc R U . . .
C8 C 0.38557(13) 0.3935(2) 0.43844(14) 0.0276(5) Uani 1 1 d . . . . .
C9 C 0.46099(15) 0.3411(2) 0.60385(15) 0.0342(5) Uani 1 1 d . . . . .
H9A H 0.444877 0.437238 0.624632 0.041 Uiso 1 1 calc R U . . .
H9B H 0.526705 0.321987 0.625189 0.041 Uiso 1 1 calc R U . . .
C10 C 0.39507(19) 0.2397(3) 0.65510(16) 0.0453(6) Uani 1 1 d . . . . .
H10A H 0.401055 0.249595 0.727784 0.068 Uiso 1 1 calc R U . . .
H10B H 0.329828 0.259424 0.635090 0.068 Uiso 1 1 calc R U . . .
H10C H 0.411608 0.144240 0.635647 0.068 Uiso 1 1 calc R U . . .
C11 C 0.58444(15) 0.1546(2) 0.47678(17) 0.0367(5) Uani 1 1 d . . . . .
H11A H 0.591644 0.175560 0.548119 0.055 Uiso 1 1 calc R U . . .
H11B H 0.571076 0.055055 0.468258 0.055 Uiso 1 1 calc R U . . .
H11C H 0.642937 0.178308 0.441462 0.055 Uiso 1 1 calc R U . . .
C12 C 0.500000 0.1581(3) 0.250000 0.0313(6) Uani 1 2 d S T P . .
H12A H 0.448590 0.098980 0.230090 0.038 Uiso 1 1 d R U . . .


_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
N1 C8 1.378(2) . ?
N1 C1 1.387(3) . ?
N1 C9 1.461(3) . ?
C1 C2 1.371(3) . ?
C1 C11 1.499(3) . ?
C2 C3 1.437(3) . ?
C2 C12 1.508(2) . ?
C3 C4 1.403(3) . ?
C3 C8 1.410(3) . ?
C4 C5 1.384(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.395(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.394(3) . ?
C7 H7A 0.9500 . ?
C9 C10 1.512(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12A 0.9600 3_655 ?

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 N1 C1 108.65(16) . . ?
C8 N1 C9 123.99(17) . . ?
C1 N1 C9 126.36(16) . . ?
C2 C1 N1 109.80(17) . . ?
C2 C1 C11 129.77(19) . . ?
N1 C1 C11 120.42(18) . . ?
C1 C2 C3 106.59(17) . . ?
C1 C2 C12 128.04(17) . . ?
C3 C2 C12 125.34(16) . . ?
C4 C3 C8 118.84(18) . . ?
C4 C3 C2 133.97(19) . . ?
C8 C3 C2 107.19(16) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C5 C6 121.51(19) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C6 C7 C8 117.5(2) . . ?
C6 C7 H7A 121.2 . . ?
C8 C7 H7A 121.2 . . ?
N1 C8 C7 129.93(19) . . ?
N1 C8 C3 107.74(17) . . ?
C7 C8 C3 122.33(18) . . ?
N1 C9 C10 111.71(18) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 C2 114.8(2) . 3_655 ?
C2 C12 H12A 108.6 . . ?
C2 C12 H12A 108.5 3_655 . ?
C2 C12 H12A 108.50(9) . 3_655 ?
C2 C12 H12A 108.59(8) 3_655 3_655 ?
H12A C12 H12A 107.6 . 3_655 ?

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 N1 C1 C2 1.1(2) . . . . ?
C9 N1 C1 C2 170.00(18) . . . . ?
C8 N1 C1 C11 -179.93(17) . . . . ?
C9 N1 C1 C11 -11.0(3) . . . . ?
N1 C1 C2 C3 -0.3(2) . . . . ?
C11 C1 C2 C3 -179.12(19) . . . . ?
N1 C1 C2 C12 -178.44(17) . . . . ?
C11 C1 C2 C12 2.7(3) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?
C12 C2 C3 C4 -2.0(3) . . . . ?
C1 C2 C3 C8 -0.6(2) . . . . ?
C12 C2 C3 C8 177.61(17) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C5 179.98(19) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C1 N1 C8 C7 178.86(19) . . . . ?
C9 N1 C8 C7 9.6(3) . . . . ?
C1 N1 C8 C3 -1.5(2) . . . . ?
C9 N1 C8 C3 -170.68(17) . . . . ?
C6 C7 C8 N1 178.22(19) . . . . ?
C6 C7 C8 C3 -1.4(3) . . . . ?
C4 C3 C8 N1 -179.05(16) . . . . ?
C2 C3 C8 N1 1.3(2) . . . . ?
C4 C3 C8 C7 0.7(3) . . . . ?
C2 C3 C8 C7 -179.02(17) . . . . ?
C8 N1 C9 C10 81.4(2) . . . . ?
C1 N1 C9 C10 -85.9(2) . . . . ?
C1 C2 C12 C2 -123.1(2) . . . 3_655 ?
C3 C2 C12 C2 59.10(16) . . . 3_655 ?

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_Compound5g
_database_code_depnum_ccdc_archive 'CCDC 2056483'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 Br2 O6'
_chemical_formula_sum            'C23 H22 Br2 O6'
_chemical_formula_weight         554.22

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'
Br Br -0.6763 1.2805 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.6128(9)
_cell_length_b                   12.3072(6)
_cell_length_c                   9.3607(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2259.47(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3013
_cell_measurement_theta_min      5.9170
_cell_measurement_theta_max      71.5710

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.869
_shelx_estimated_absorpt_T_min   0.443
_shelx_estimated_absorpt_T_max   0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            6485
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.241
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.723
_diffrn_reflns_point_group_measured_fraction_full 0.731
_reflns_number_total             3101
_reflns_number_gt                2867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.362
_reflns_Friedel_fraction_max     0.411
_reflns_Friedel_fraction_full    0.424

_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0678P)²+0.9057P] 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_abs_structure_details 
; 
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.06(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3101
_refine_ls_number_parameters     326
_refine_ls_number_restraints     487
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.013
_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
Br1 Br 0.83033(4) -0.51116(5) -0.01758(11) 0.0583(2) Uani 1 1 d . U . . .
Br2 Br 0.92557(3) 0.59029(5) 0.63528(8) 0.0465(2) Uani 1 1 d . U . . .
O1 O 1.0030(2) -0.1102(3) 0.3335(5) 0.0355(8) Uani 1 1 d . U . . .
O2 O 1.0351(2) 0.1522(4) 0.2369(5) 0.0428(10) Uani 1 1 d . U . . .
O3 O 1.08224(18) 0.0197(4) 0.1057(5) 0.0365(9) Uani 1 1 d . U . . .
O4 O 0.7704(2) 0.2139(4) 0.2034(6) 0.0429(10) Uani 1 1 d . U . . .
C1 C 0.8957(3) -0.1946(5) 0.0379(7) 0.0341(11) Uani 1 1 d . U . . .
H1A H 0.890312 -0.127124 -0.010044 0.041 Uiso 1 1 calc R U . . .
C2 C 0.8642(3) -0.2872(4) -0.0171(8) 0.0370(11) Uani 1 1 d . U . . .
H2A H 0.838316 -0.283681 -0.102782 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8713(3) -0.3839(5) 0.0554(7) 0.0389(11) Uani 1 1 d . U . . .
C4 C 0.9101(3) -0.3914(5) 0.1782(7) 0.0373(11) Uani 1 1 d . U . . .
H4A H 0.915288 -0.459331 0.225219 0.045 Uiso 1 1 calc R U . . .
C5 C 0.9413(3) -0.2991(5) 0.2321(7) 0.0339(11) Uani 1 1 d . U . . .
H5A H 0.967215 -0.303524 0.317615 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9348(3) -0.1994(4) 0.1616(6) 0.0281(10) Uani 1 1 d . U . . .
C7 C 0.9704(3) -0.1035(4) 0.2216(7) 0.0282(9) Uani 1 1 d . U . . .
C9 C 1.0302(3) 0.0690(5) 0.1699(7) 0.0325(10) Uani 1 1 d . U . . .
C10 C 1.1483(3) 0.0723(5) 0.1197(8) 0.0401(12) Uani 1 1 d . U . . .
H10A H 1.184437 0.016307 0.124426 0.048 Uiso 1 1 calc R U . . .
H10B H 1.149506 0.114505 0.209670 0.048 Uiso 1 1 calc R U . . .
C11 C 1.1617(3) 0.1461(5) -0.0031(8) 0.0397(12) Uani 1 1 d . U . . .
H11A H 1.206432 0.180438 0.008968 0.060 Uiso 1 1 calc R U . . .
H11B H 1.161243 0.104161 -0.092056 0.060 Uiso 1 1 calc R U . . .
H11C H 1.126350 0.202252 -0.006905 0.060 Uiso 1 1 calc R U . . .
C13 C 0.9231(3) 0.3276(5) 0.3610(7) 0.0317(11) Uani 1 1 d . U . . .
H13A H 0.955985 0.279604 0.321240 0.038 Uiso 1 1 calc R U . . .
C14 C 0.9435(3) 0.4070(5) 0.4567(7) 0.0339(11) Uani 1 1 d . U . . .
H14A H 0.990180 0.413101 0.482859 0.041 Uiso 1 1 calc R U . . .
C15 C 0.8960(3) 0.4775(5) 0.5141(7) 0.0354(11) Uani 1 1 d . U . . .
C16 C 0.8268(3) 0.4694(5) 0.4785(9) 0.0376(11) Uani 1 1 d . U . . .
H16A H 0.794304 0.517924 0.518382 0.045 Uiso 1 1 calc R U . . .
C17 C 0.8068(3) 0.3887(5) 0.3834(7) 0.0345(11) Uani 1 1 d . U . . .
H17A H 0.759952 0.381625 0.359018 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8547(3) 0.3175(5) 0.3227(7) 0.0305(10) Uani 1 1 d . U . . .
C19 C 0.8303(3) 0.2340(5) 0.2183(7) 0.0319(10) Uani 1 1 d . U . . .
O5 O 0.8403(4) 0.0611(6) -0.0629(9) 0.0309(14) Uani 0.745(8) 1 d . U P A 1
O6 O 0.8624(3) 0.2391(4) -0.0985(6) 0.0328(11) Uani 0.745(8) 1 d . U P A 1
C8 C 0.9640(2) 0.0063(4) 0.1471(7) 0.0282(8) Uani 0.745(8) 1 d . U P A 1
H8A H 0.956336 -0.005033 0.042557 0.034 Uiso 0.745(8) 1 calc R U P A 1
C12 C 0.9023(3) 0.0668(4) 0.2125(6) 0.0273(8) Uani 0.745(8) 1 d . U P A 1
H12A H 0.862365 0.017532 0.212505 0.033 Uiso 0.745(8) 1 calc R U P A 1
H12B H 0.912747 0.085371 0.312992 0.033 Uiso 0.745(8) 1 calc R U P A 1
C20 C 0.8838(2) 0.1710(4) 0.1316(7) 0.0290(7) Uani 0.745(8) 1 d . U P A 1
H20A H 0.925725 0.216928 0.125248 0.035 Uiso 0.745(8) 1 calc R U P A 1
C21 C 0.8591(4) 0.1487(8) -0.0203(12) 0.0309(12) Uani 0.745(8) 1 d . U P A 1
C22 C 0.8487(5) 0.2259(7) -0.2499(10) 0.0359(13) Uani 0.745(8) 1 d . U P A 1
H22A H 0.868430 0.156292 -0.283078 0.043 Uiso 0.745(8) 1 calc R U P A 1
H22B H 0.870963 0.285443 -0.303538 0.043 Uiso 0.745(8) 1 calc R U P A 1
C23 C 0.7742(5) 0.2269(8) -0.2798(11) 0.0429(16) Uani 0.745(8) 1 d . U P A 1
H23A H 0.766576 0.217822 -0.382569 0.064 Uiso 0.745(8) 1 calc R U P A 1
H23B H 0.752181 0.167184 -0.228018 0.064 Uiso 0.745(8) 1 calc R U P A 1
H23C H 0.754711 0.296220 -0.248459 0.064 Uiso 0.745(8) 1 calc R U P A 1
O5' O 0.8291(14) 0.043(2) -0.038(3) 0.031(2) Uani 0.255(8) 1 d . U P A 2
O6' O 0.8219(10) 0.2298(13) -0.0790(19) 0.0331(15) Uani 0.255(8) 1 d . U P A 2
C8' C 0.9640(2) 0.0063(4) 0.1471(7) 0.0282(8) Uani 0.255(8) 1 d . U P A 2
H8'A H 0.956336 -0.005033 0.042557 0.034 Uiso 0.255(8) 1 calc R U P A 2
C12' C 0.9023(3) 0.0668(4) 0.2125(6) 0.0273(8) Uani 0.255(8) 1 d . U P A 2
H12C H 0.862365 0.017532 0.212505 0.033 Uiso 0.255(8) 1 calc R U P A 2
H12D H 0.912747 0.085371 0.312992 0.033 Uiso 0.255(8) 1 calc R U P A 2
C20' C 0.8838(2) 0.1710(4) 0.1316(7) 0.0290(7) Uani 0.255(8) 1 d . U P A 2
H20B H 0.924712 0.216153 0.108528 0.035 Uiso 0.255(8) 1 calc R U P A 2
C21' C 0.8427(14) 0.139(3) -0.003(4) 0.0312(14) Uani 0.255(8) 1 d . U P A 2
C22' C 0.7899(14) 0.209(2) -0.208(3) 0.0363(17) Uani 0.255(8) 1 d . U P A 2
H22C H 0.754174 0.265017 -0.223656 0.044 Uiso 0.255(8) 1 calc R U P A 2
H22D H 0.767251 0.137672 -0.203169 0.044 Uiso 0.255(8) 1 calc R U P A 2
C23' C 0.8365(14) 0.210(2) -0.328(3) 0.040(2) Uani 0.255(8) 1 d . U P A 2
H23D H 0.811256 0.195630 -0.416449 0.059 Uiso 0.255(8) 1 calc R U P A 2
H23E H 0.858384 0.281855 -0.335050 0.059 Uiso 0.255(8) 1 calc R U P A 2
H23F H 0.871467 0.154456 -0.314554 0.059 Uiso 0.255(8) 1 calc R U P A 2


_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
Br1 C3 1.889(6) . ?
Br2 C15 1.884(6) . ?
O1 C7 1.230(8) . ?
O2 C9 1.205(7) . ?
O3 C9 1.332(7) . ?
O3 C10 1.454(7) . ?
O4 C19 1.208(7) . ?
C1 C6 1.390(9) . ?
C1 C2 1.395(8) . ?
C1 H1A 0.9500 . ?
C2 C3 1.377(9) . ?
C2 H2A 0.9500 . ?
C3 C4 1.381(10) . ?
C4 C5 1.386(9) . ?
C4 H4A 0.9500 . ?
C5 C6 1.399(8) . ?
C5 H5A 0.9500 . ?
C6 C7 1.481(8) . ?
C7 C8' 1.525(7) . ?
C7 C8 1.525(7) . ?
C9 C8' 1.524(7) . ?
C9 C8 1.524(7) . ?
C10 C11 1.488(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.385(9) . ?
C13 C18 1.395(8) . ?
C13 H13A 0.9500 . ?
C14 C15 1.382(9) . ?
C14 H14A 0.9500 . ?
C15 C16 1.401(8) . ?
C16 C17 1.390(9) . ?
C16 H16A 0.9500 . ?
C17 C18 1.406(8) . ?
C17 H17A 0.9500 . ?
C18 C19 1.497(8) . ?
C19 C20' 1.536(8) . ?
C19 C20 1.536(8) . ?
O5 C21 1.207(12) . ?
O6 C21 1.333(11) . ?
O6 C22 1.451(11) . ?
C8 C12 1.547(7) . ?
C8 H8A 1.0000 . ?
C12 C20 1.533(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C20 C21 1.526(13) . ?
C20 H20A 1.0000 . ?
C22 C23 1.488(13) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5' C21' 1.26(4) . ?
O6' C21' 1.38(3) . ?
O6' C22' 1.38(3) . ?
C8' C12' 1.547(7) . ?
C8' H8'A 1.0000 . ?
C12' C20' 1.533(7) . ?
C12' H12C 0.9900 . ?
C12' H12D 0.9900 . ?
C20' C21' 1.55(3) . ?
C20' H20B 1.0000 . ?
C22' C23' 1.45(4) . ?
C22' H22C 0.9900 . ?
C22' H22D 0.9900 . ?
C23' H23D 0.9800 . ?
C23' H23E 0.9800 . ?
C23' H23F 0.9800 . ?

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
C9 O3 C10 116.1(5) . . ?
C6 C1 C2 121.2(5) . . ?
C6 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 118.6(6) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 121.6(6) . . ?
C2 C3 Br1 119.7(5) . . ?
C4 C3 Br1 118.6(5) . . ?
C3 C4 C5 119.4(6) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 C6 120.5(6) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C1 C6 C5 118.7(5) . . ?
C1 C6 C7 122.8(5) . . ?
C5 C6 C7 118.5(5) . . ?
O1 C7 C6 120.9(5) . . ?
O1 C7 C8' 119.4(5) . . ?
C6 C7 C8' 119.6(5) . . ?
O1 C7 C8 119.4(5) . . ?
C6 C7 C8 119.6(5) . . ?
O2 C9 O3 124.1(5) . . ?
O2 C9 C8' 124.9(5) . . ?
O3 C9 C8' 111.0(5) . . ?
O2 C9 C8 124.9(5) . . ?
O3 C9 C8 111.0(5) . . ?
O3 C10 C11 111.1(5) . . ?
O3 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
O3 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C13 C18 120.5(5) . . ?
C14 C13 H13A 119.8 . . ?
C18 C13 H13A 119.8 . . ?
C15 C14 C13 120.0(5) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 121.1(6) . . ?
C14 C15 Br2 119.3(5) . . ?
C16 C15 Br2 119.6(5) . . ?
C17 C16 C15 118.5(6) . . ?
C17 C16 H16A 120.7 . . ?
C15 C16 H16A 120.7 . . ?
C16 C17 C18 121.0(5) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
C13 C18 C17 119.0(5) . . ?
C13 C18 C19 122.5(5) . . ?
C17 C18 C19 118.6(5) . . ?
O4 C19 C18 121.7(6) . . ?
O4 C19 C20' 120.0(6) . . ?
C18 C19 C20' 118.3(5) . . ?
O4 C19 C20 120.0(6) . . ?
C18 C19 C20 118.3(5) . . ?
C21 O6 C22 115.7(7) . . ?
C9 C8 C7 108.4(4) . . ?
C9 C8 C12 111.5(4) . . ?
C7 C8 C12 108.0(4) . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C12 C8 H8A 109.6 . . ?
C20 C12 C8 113.1(5) . . ?
C20 C12 H12A 109.0 . . ?
C8 C12 H12A 109.0 . . ?
C20 C12 H12B 109.0 . . ?
C8 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C21 C20 C12 112.6(5) . . ?
C21 C20 C19 111.5(5) . . ?
C12 C20 C19 108.8(5) . . ?
C21 C20 H20A 107.9 . . ?
C12 C20 H20A 107.9 . . ?
C19 C20 H20A 107.9 . . ?
O5 C21 O6 125.4(10) . . ?
O5 C21 C20 124.4(8) . . ?
O6 C21 C20 110.2(7) . . ?
O6 C22 C23 111.3(8) . . ?
O6 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
O6 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21' O6' C22' 116(2) . . ?
C9 C8' C7 108.4(4) . . ?
C9 C8' C12' 111.5(4) . . ?
C7 C8' C12' 108.0(4) . . ?
C9 C8' H8'A 109.6 . . ?
C7 C8' H8'A 109.6 . . ?
C12' C8' H8'A 109.6 . . ?
C20' C12' C8' 113.1(5) . . ?
C20' C12' H12C 109.0 . . ?
C8' C12' H12C 109.0 . . ?
C20' C12' H12D 109.0 . . ?
C8' C12' H12D 109.0 . . ?
H12C C12' H12D 107.8 . . ?
C12' C20' C19 108.8(5) . . ?
C12' C20' C21' 108.5(12) . . ?
C19 C20' C21' 101.7(12) . . ?
C12' C20' H20B 112.4 . . ?
C19 C20' H20B 112.4 . . ?
C21' C20' H20B 112.4 . . ?
O5' C21' O6' 125(3) . . ?
O5' C21' C20' 124(3) . . ?
O6' C21' C20' 112(2) . . ?
O6' C22' C23' 113(2) . . ?
O6' C22' H22C 109.0 . . ?
C23' C22' H22C 109.0 . . ?
O6' C22' H22D 109.0 . . ?
C23' C22' H22D 109.0 . . ?
H22C C22' H22D 107.8 . . ?
C22' C23' H23D 109.5 . . ?
C22' C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22' C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?

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 1.4(9) . . . . ?
C1 C2 C3 C4 -1.6(10) . . . . ?
C1 C2 C3 Br1 -179.1(5) . . . . ?
C2 C3 C4 C5 1.6(10) . . . . ?
Br1 C3 C4 C5 179.1(5) . . . . ?
C3 C4 C5 C6 -1.3(9) . . . . ?
C2 C1 C6 C5 -1.1(8) . . . . ?
C2 C1 C6 C7 178.6(5) . . . . ?
C4 C5 C6 C1 1.0(8) . . . . ?
C4 C5 C6 C7 -178.6(5) . . . . ?
C1 C6 C7 O1 177.9(5) . . . . ?
C5 C6 C7 O1 -2.4(8) . . . . ?
C1 C6 C7 C8' 0.6(8) . . . . ?
C5 C6 C7 C8' -179.8(5) . . . . ?
C1 C6 C7 C8 0.6(8) . . . . ?
C5 C6 C7 C8 -179.8(5) . . . . ?
C10 O3 C9 O2 -0.1(9) . . . . ?
C10 O3 C9 C8' 179.9(5) . . . . ?
C10 O3 C9 C8 179.9(5) . . . . ?
C9 O3 C10 C11 -93.3(7) . . . . ?
C18 C13 C14 C15 -0.5(9) . . . . ?
C13 C14 C15 C16 0.7(10) . . . . ?
C13 C14 C15 Br2 -176.3(5) . . . . ?
C14 C15 C16 C17 -0.1(10) . . . . ?
Br2 C15 C16 C17 176.9(5) . . . . ?
C15 C16 C17 C18 -0.7(10) . . . . ?
C14 C13 C18 C17 -0.4(9) . . . . ?
C14 C13 C18 C19 179.1(6) . . . . ?
C16 C17 C18 C13 1.0(9) . . . . ?
C16 C17 C18 C19 -178.5(6) . . . . ?
C13 C18 C19 O4 167.6(6) . . . . ?
C17 C18 C19 O4 -12.8(9) . . . . ?
C13 C18 C19 C20' -10.8(9) . . . . ?
C17 C18 C19 C20' 168.7(5) . . . . ?
C13 C18 C19 C20 -10.8(9) . . . . ?
C17 C18 C19 C20 168.7(5) . . . . ?
O2 C9 C8 C7 -114.9(6) . . . . ?
O3 C9 C8 C7 65.1(6) . . . . ?
O2 C9 C8 C12 3.8(9) . . . . ?
O3 C9 C8 C12 -176.1(5) . . . . ?
O1 C7 C8 C9 34.4(7) . . . . ?
C6 C7 C8 C9 -148.2(5) . . . . ?
O1 C7 C8 C12 -86.6(6) . . . . ?
C6 C7 C8 C12 90.8(6) . . . . ?
C9 C8 C12 C20 69.7(6) . . . . ?
C7 C8 C12 C20 -171.3(5) . . . . ?
C8 C12 C20 C21 65.1(6) . . . . ?
C8 C12 C20 C19 -170.7(4) . . . . ?
O4 C19 C20 C21 37.9(8) . . . . ?
C18 C19 C20 C21 -143.5(6) . . . . ?
O4 C19 C20 C12 -86.9(7) . . . . ?
C18 C19 C20 C12 91.6(6) . . . . ?
C22 O6 C21 O5 -6.7(12) . . . . ?
C22 O6 C21 C20 172.3(6) . . . . ?
C12 C20 C21 O5 16.8(10) . . . . ?
C19 C20 C21 O5 -105.9(9) . . . . ?
C12 C20 C21 O6 -162.3(6) . . . . ?
C19 C20 C21 O6 75.1(7) . . . . ?
C21 O6 C22 C23 83.5(9) . . . . ?
O2 C9 C8' C7 -114.9(6) . . . . ?
O3 C9 C8' C7 65.1(6) . . . . ?
O2 C9 C8' C12' 3.8(9) . . . . ?
O3 C9 C8' C12' -176.1(5) . . . . ?
O1 C7 C8' C9 34.4(7) . . . . ?
C6 C7 C8' C9 -148.2(5) . . . . ?
O1 C7 C8' C12' -86.6(6) . . . . ?
C6 C7 C8' C12' 90.8(6) . . . . ?
C9 C8' C12' C20' 69.7(6) . . . . ?
C7 C8' C12' C20' -171.3(5) . . . . ?
C8' C12' C20' C19 -170.7(4) . . . . ?
C8' C12' C20' C21' 79.5(12) . . . . ?
O4 C19 C20' C12' -86.9(7) . . . . ?
C18 C19 C20' C12' 91.6(6) . . . . ?
O4 C19 C20' C21' 27.5(13) . . . . ?
C18 C19 C20' C21' -154.0(12) . . . . ?
C22' O6' C21' O5' -7(4) . . . . ?
C22' O6' C21' C20' 174.6(19) . . . . ?
C12' C20' C21' O5' -1(3) . . . . ?
C19 C20' C21' O5' -116(2) . . . . ?
C12' C20' C21' O6' 177.7(16) . . . . ?
C19 C20' C21' O6' 63(2) . . . . ?
C21' O6' C22' C23' -93(3) . . . . ?

_refine_diff_density_max         0.617
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_Compound3m
_database_code_depnum_ccdc_archive 'CCDC 2056482'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 Cl2 N2'
_chemical_formula_sum            'C21 H20 Cl2 N2'
_chemical_formula_weight         371.29

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'
Cl Cl 0.3639 0.7018 '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'

_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                   8.8647(5)
_cell_length_b                   10.0294(6)
_cell_length_c                   11.7597(5)
_cell_angle_alpha                110.640(5)
_cell_angle_beta                 90.771(4)
_cell_angle_gamma                112.601(5)
_cell_volume                     889.76(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2922
_cell_measurement_theta_min      4.0470
_cell_measurement_theta_max      72.2960

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.310
_shelx_estimated_absorpt_T_min   0.557
_shelx_estimated_absorpt_T_max   0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            6815
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.078
_diffrn_reflns_theta_max         69.924
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3346
_reflns_number_gt                2884
_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0859P)²+0.7289P] 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         3346
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
Cl1 Cl 0.47277(8) 1.03059(8) 0.66148(6) 0.0354(2) Uani 1 1 d . . . . .
Cl2 Cl 0.27713(9) 0.01264(8) -0.05341(6) 0.0348(2) Uani 1 1 d . . . . .
N1 N 0.2666(3) 0.3603(3) 0.5326(2) 0.0299(5) Uani 1 1 d . . . . .
N2 N 0.2051(3) 0.6018(2) 0.0886(2) 0.0271(5) Uani 1 1 d . . . . .
C1 C 0.1441(3) 0.3009(3) 0.4301(2) 0.0289(6) Uani 1 1 d . . . . .
C2 C 0.1360(3) 0.4219(3) 0.4057(2) 0.0257(5) Uani 1 1 d . . . . .
C3 C 0.2558(3) 0.5640(3) 0.4981(2) 0.0251(5) Uani 1 1 d . . . . .
C4 C 0.2984(3) 0.7225(3) 0.5252(2) 0.0259(5) Uani 1 1 d . . . . .
H4A H 0.247421 0.754584 0.474525 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4165(3) 0.8311(3) 0.6276(2) 0.0280(6) Uani 1 1 d . . . . .
C6 C 0.4952(3) 0.7890(4) 0.7047(2) 0.0330(6) Uani 1 1 d . . . . .
H6A H 0.575757 0.867808 0.774590 0.040 Uiso 1 1 calc R U . . .
C7 C 0.4555(3) 0.6329(4) 0.6790(2) 0.0323(6) Uani 1 1 d . . . . .
H7A H 0.508312 0.602619 0.730078 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3353(3) 0.5206(3) 0.5758(2) 0.0278(5) Uani 1 1 d . . . . .
C9 C 0.3178(4) 0.2686(4) 0.5835(3) 0.0367(7) Uani 1 1 d . . . . .
H9A H 0.249740 0.156839 0.536575 0.055 Uiso 1 1 calc R U . . .
H9B H 0.434747 0.291308 0.578232 0.055 Uiso 1 1 calc R U . . .
H9C H 0.303517 0.295861 0.670047 0.055 Uiso 1 1 calc R U . . .
C10 C 0.0460(4) 0.1283(3) 0.3653(3) 0.0392(7) Uani 1 1 d . . . . .
H10A H 0.082853 0.073657 0.406305 0.059 Uiso 1 1 calc R U . . .
H10B H -0.071948 0.102841 0.367657 0.059 Uiso 1 1 calc R U . . .
H10C H 0.062803 0.095231 0.279253 0.059 Uiso 1 1 calc R U . . .
C11 C 0.0207(3) 0.4137(3) 0.3058(2) 0.0271(5) Uani 1 1 d . . . . .
H11A H -0.063228 0.304315 0.264745 0.032 Uiso 1 1 calc R U . . .
H11B H -0.038640 0.479497 0.344421 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1254(3) 0.5986(3) 0.1891(2) 0.0256(5) Uani 1 1 d . . . . .
C13 C 0.1045(3) 0.4662(3) 0.2093(2) 0.0245(5) Uani 1 1 d . . . . .
C14 C 0.1727(3) 0.3814(3) 0.1160(2) 0.0227(5) Uani 1 1 d . . . . .
C15 C 0.1849(3) 0.2376(3) 0.0860(2) 0.0247(5) Uani 1 1 d . . . . .
H15A H 0.144744 0.175738 0.133490 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2572(3) 0.1895(3) -0.0146(2) 0.0260(5) Uani 1 1 d . . . . .
C17 C 0.3172(3) 0.2762(3) -0.0878(2) 0.0282(6) Uani 1 1 d . . . . .
H17A H 0.365848 0.237921 -0.156353 0.034 Uiso 1 1 calc R U . . .
C18 C 0.3056(3) 0.4172(3) -0.0603(2) 0.0267(5) Uani 1 1 d . . . . .
H18A H 0.345240 0.477201 -0.109153 0.032 Uiso 1 1 calc R U . . .
C19 C 0.2337(3) 0.4690(3) 0.0420(2) 0.0242(5) Uani 1 1 d . . . . .
C20 C 0.2459(4) 0.7206(3) 0.0362(3) 0.0328(6) Uani 1 1 d . . . . .
H20A H 0.213640 0.803659 0.085738 0.049 Uiso 1 1 calc R U . . .
H20B H 0.365573 0.765352 0.036287 0.049 Uiso 1 1 calc R U . . .
H20C H 0.186003 0.672743 -0.048652 0.049 Uiso 1 1 calc R U . . .
C21 C 0.0734(3) 0.7267(3) 0.2573(3) 0.0336(6) Uani 1 1 d . . . . .
H21A H 0.106449 0.805030 0.220300 0.050 Uiso 1 1 calc R U . . .
H21B H -0.047330 0.682453 0.252193 0.050 Uiso 1 1 calc R U . . .
H21C H 0.127050 0.776263 0.343977 0.050 Uiso 1 1 calc R U . . .


_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
Cl1 C5 1.754(3) . ?
Cl2 C16 1.749(3) . ?
N1 C8 1.370(4) . ?
N1 C1 1.396(4) . ?
N1 C9 1.453(3) . ?
N2 C19 1.375(3) . ?
N2 C12 1.389(3) . ?
N2 C20 1.457(3) . ?
C1 C2 1.368(4) . ?
C1 C10 1.493(4) . ?
C2 C3 1.433(4) . ?
C2 C11 1.506(4) . ?
C3 C4 1.396(4) . ?
C3 C8 1.421(4) . ?
C4 C5 1.377(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(4) . ?
C6 C7 1.380(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.398(4) . ?
C7 H7A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.503(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.374(4) . ?
C12 C21 1.498(4) . ?
C13 C14 1.431(3) . ?
C14 C15 1.407(3) . ?
C14 C19 1.417(3) . ?
C15 C16 1.377(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.402(4) . ?
C17 C18 1.380(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.399(4) . ?
C18 H18A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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 N1 C1 108.7(2) . . ?
C8 N1 C9 125.1(2) . . ?
C1 N1 C9 126.1(2) . . ?
C19 N2 C12 108.4(2) . . ?
C19 N2 C20 124.8(2) . . ?
C12 N2 C20 126.7(2) . . ?
C2 C1 N1 109.6(2) . . ?
C2 C1 C10 130.1(3) . . ?
N1 C1 C10 120.3(2) . . ?
C1 C2 C3 106.9(2) . . ?
C1 C2 C11 128.2(2) . . ?
C3 C2 C11 124.8(2) . . ?
C4 C3 C8 119.3(2) . . ?
C4 C3 C2 133.6(2) . . ?
C8 C3 C2 107.0(2) . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4A 121.0 . . ?
C3 C4 H4A 121.0 . . ?
C4 C5 C6 122.9(3) . . ?
C4 C5 Cl1 118.4(2) . . ?
C6 C5 Cl1 118.7(2) . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C6 C7 C8 118.2(2) . . ?
C6 C7 H7A 120.9 . . ?
C8 C7 H7A 120.9 . . ?
N1 C8 C7 130.6(2) . . ?
N1 C8 C3 107.7(2) . . ?
C7 C8 C3 121.6(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C2 114.6(2) . . ?
C13 C11 H11A 108.6 . . ?
C2 C11 H11A 108.6 . . ?
C13 C11 H11B 108.6 . . ?
C2 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 N2 110.0(2) . . ?
C13 C12 C21 129.3(2) . . ?
N2 C12 C21 120.7(2) . . ?
C12 C13 C14 106.5(2) . . ?
C12 C13 C11 127.9(2) . . ?
C14 C13 C11 125.6(2) . . ?
C15 C14 C19 119.1(2) . . ?
C15 C14 C13 133.7(2) . . ?
C19 C14 C13 107.2(2) . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 H15A 121.2 . . ?
C14 C15 H15A 121.2 . . ?
C15 C16 C17 123.2(2) . . ?
C15 C16 Cl2 119.0(2) . . ?
C17 C16 Cl2 117.83(19) . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C17 C18 C19 117.8(2) . . ?
C17 C18 H18A 121.1 . . ?
C19 C18 H18A 121.1 . . ?
N2 C19 C18 129.9(2) . . ?
N2 C19 C14 107.8(2) . . ?
C18 C19 C14 122.2(2) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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 N1 C1 C2 1.1(3) . . . . ?
C9 N1 C1 C2 -176.9(2) . . . . ?
C8 N1 C1 C10 -178.9(2) . . . . ?
C9 N1 C1 C10 3.0(4) . . . . ?
N1 C1 C2 C3 -1.2(3) . . . . ?
C10 C1 C2 C3 178.8(3) . . . . ?
N1 C1 C2 C11 -178.8(2) . . . . ?
C10 C1 C2 C11 1.3(5) . . . . ?
C1 C2 C3 C4 -176.2(3) . . . . ?
C11 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C8 0.8(3) . . . . ?
C11 C2 C3 C8 178.5(2) . . . . ?
C8 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C4 C5 176.4(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 Cl1 179.25(18) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
Cl1 C5 C6 C7 -178.9(2) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C1 N1 C8 C7 176.4(3) . . . . ?
C9 N1 C8 C7 -5.5(4) . . . . ?
C1 N1 C8 C3 -0.6(3) . . . . ?
C9 N1 C8 C3 177.5(2) . . . . ?
C6 C7 C8 N1 -176.3(3) . . . . ?
C6 C7 C8 C3 0.3(4) . . . . ?
C4 C3 C8 N1 177.3(2) . . . . ?
C2 C3 C8 N1 -0.2(3) . . . . ?
C4 C3 C8 C7 0.0(4) . . . . ?
C2 C3 C8 C7 -177.5(2) . . . . ?
C1 C2 C11 C13 -113.6(3) . . . . ?
C3 C2 C11 C13 69.2(3) . . . . ?
C19 N2 C12 C13 0.9(3) . . . . ?
C20 N2 C12 C13 178.4(2) . . . . ?
C19 N2 C12 C21 -178.2(2) . . . . ?
C20 N2 C12 C21 -0.8(4) . . . . ?
N2 C12 C13 C14 -0.7(3) . . . . ?
C21 C12 C13 C14 178.4(2) . . . . ?
N2 C12 C13 C11 -178.3(2) . . . . ?
C21 C12 C13 C11 0.8(4) . . . . ?
C2 C11 C13 C12 -110.6(3) . . . . ?
C2 C11 C13 C14 72.3(3) . . . . ?
C12 C13 C14 C15 -178.2(3) . . . . ?
C11 C13 C14 C15 -0.5(4) . . . . ?
C12 C13 C14 C19 0.1(3) . . . . ?
C11 C13 C14 C19 177.8(2) . . . . ?
C19 C14 C15 C16 0.3(3) . . . . ?
C13 C14 C15 C16 178.5(2) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C14 C15 C16 Cl2 179.13(18) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
Cl2 C16 C17 C18 -179.45(19) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C12 N2 C19 C18 178.0(2) . . . . ?
C20 N2 C19 C18 0.5(4) . . . . ?
C12 N2 C19 C14 -0.8(3) . . . . ?
C20 N2 C19 C14 -178.3(2) . . . . ?
C17 C18 C19 N2 -179.1(2) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
C15 C14 C19 N2 179.0(2) . . . . ?
C13 C14 C19 N2 0.4(3) . . . . ?
C15 C14 C19 C18 0.1(4) . . . . ?
C13 C14 C19 C18 -178.5(2) . . . . ?

_refine_diff_density_max         0.620
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_Compound3j
_database_code_depnum_ccdc_archive 'CCDC 2056480'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H30 N2'
_chemical_formula_sum            'C33 H30 N2'
_chemical_formula_weight         454.59

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'

_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                   5.5415(2)
_cell_length_b                   10.2343(5)
_cell_length_c                   21.6380(10)
_cell_angle_alpha                86.297(4)
_cell_angle_beta                 89.697(4)
_cell_angle_gamma                87.381(4)
_cell_volume                     1223.32(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3109
_cell_measurement_theta_min      4.0820
_cell_measurement_theta_max      72.4790

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.545
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            9490
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.095
_diffrn_reflns_theta_max         69.995
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4590
_reflns_number_gt                3594
_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1277P)²+0.2633P] 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         4590
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.2001
_refine_ls_wR_factor_gt          0.1837
_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
N1 N 0.2788(4) 0.7656(2) 0.38223(9) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.6384(3) 0.51841(17) 0.14673(8) 0.0288(4) Uani 1 1 d . . . . .
C1 C 0.4611(4) 0.6714(2) 0.37317(10) 0.0340(5) Uani 1 1 d . . . . .
C2 C 0.6041(4) 0.7111(2) 0.32445(10) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.5065(4) 0.8372(2) 0.30155(10) 0.0290(5) Uani 1 1 d . . . . .
C4 C 0.5675(4) 0.9257(2) 0.25244(10) 0.0324(5) Uani 1 1 d . . . . .
H4A H 0.704789 0.908090 0.227302 0.039 Uiso 1 1 calc R U . . .
C5 C 0.4243(5) 1.0393(2) 0.24112(11) 0.0378(5) Uani 1 1 d . . . . .
H5A H 0.464601 1.100135 0.208091 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2210(5) 1.0653(2) 0.27775(12) 0.0406(6) Uani 1 1 d . . . . .
H6A H 0.124654 1.143322 0.268649 0.049 Uiso 1 1 calc R U . . .
C7 C 0.1569(4) 0.9811(2) 0.32659(11) 0.0370(5) Uani 1 1 d . . . . .
H7A H 0.019114 0.999698 0.351368 0.044 Uiso 1 1 calc R U . . .
C8 C 0.3015(4) 0.8675(2) 0.33834(10) 0.0312(5) Uani 1 1 d . . . . .
C9 C 0.0859(4) 0.7544(3) 0.42797(11) 0.0396(6) Uani 1 1 d . . . . .
H9A H 0.014924 0.667852 0.425615 0.048 Uiso 1 1 calc R U . . .
H9B H -0.042485 0.822294 0.416977 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1630(4) 0.7689(2) 0.49421(11) 0.0353(5) Uani 1 1 d . . . . .
C11 C 0.0193(5) 0.7196(3) 0.54202(12) 0.0427(6) Uani 1 1 d . . . . .
H11A H -0.122561 0.676115 0.532618 0.051 Uiso 1 1 calc R U . . .
C12 C 0.0793(6) 0.7328(3) 0.60339(13) 0.0550(8) Uani 1 1 d . . . . .
H12A H -0.020576 0.697699 0.635603 0.066 Uiso 1 1 calc R U . . .
C13 C 0.2830(6) 0.7965(3) 0.61773(13) 0.0573(8) Uani 1 1 d . . . . .
H13A H 0.324209 0.806045 0.659706 0.069 Uiso 1 1 calc R U . . .
C14 C 0.4261(6) 0.8462(3) 0.57060(15) 0.0570(8) Uani 1 1 d . . . . .
H14A H 0.567141 0.890181 0.580183 0.068 Uiso 1 1 calc R U . . .
C15 C 0.3667(5) 0.8328(3) 0.50910(14) 0.0498(7) Uani 1 1 d . . . . .
H15A H 0.467166 0.867893 0.477030 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4743(6) 0.5479(3) 0.41387(12) 0.0493(7) Uani 1 1 d . . . . .
H16A H 0.343846 0.550319 0.444590 0.074 Uiso 1 1 calc R U . . .
H16B H 0.457119 0.472744 0.388631 0.074 Uiso 1 1 calc R U . . .
H16C H 0.630502 0.539551 0.435108 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8175(4) 0.6368(2) 0.29789(10) 0.0342(5) Uani 1 1 d . . . . .
H17A H 0.849680 0.554760 0.323888 0.041 Uiso 1 1 calc R U . . .
H17B H 0.961499 0.690163 0.299934 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6175(4) 0.5215(2) 0.21053(10) 0.0296(5) Uani 1 1 d . . . . .
C19 C 0.7825(4) 0.6031(2) 0.23178(10) 0.0294(5) Uani 1 1 d . . . . .
C20 C 0.9152(4) 0.6532(2) 0.17892(10) 0.0283(4) Uani 1 1 d . . . . .
C21 C 1.1080(4) 0.7374(2) 0.17043(11) 0.0348(5) Uani 1 1 d . . . . .
H21A H 1.176077 0.775519 0.204834 0.042 Uiso 1 1 calc R U . . .
C22 C 1.1970(4) 0.7638(2) 0.11152(13) 0.0408(6) Uani 1 1 d . . . . .
H22A H 1.327758 0.820247 0.105665 0.049 Uiso 1 1 calc R U . . .
C23 C 1.0982(5) 0.7091(2) 0.06009(12) 0.0406(6) Uani 1 1 d . . . . .
H23A H 1.161869 0.730160 0.020013 0.049 Uiso 1 1 calc R U . . .
C24 C 0.9094(4) 0.6250(2) 0.06661(11) 0.0340(5) Uani 1 1 d . . . . .
H24A H 0.843040 0.587400 0.031856 0.041 Uiso 1 1 calc R U . . .
C25 C 0.8208(4) 0.59788(19) 0.12628(10) 0.0279(4) Uani 1 1 d . . . . .
C26 C 0.4916(4) 0.4446(2) 0.10735(11) 0.0321(5) Uani 1 1 d . . . . .
H26A H 0.489001 0.488388 0.065182 0.039 Uiso 1 1 calc R U . . .
H26B H 0.323758 0.447174 0.123298 0.039 Uiso 1 1 calc R U . . .
C27 C 0.5771(4) 0.3026(2) 0.10298(9) 0.0274(4) Uani 1 1 d . . . . .
C28 C 0.7943(4) 0.2506(2) 0.12721(11) 0.0330(5) Uani 1 1 d . . . . .
H28A H 0.897187 0.304771 0.148198 0.040 Uiso 1 1 calc R U . . .
C29 C 0.8632(4) 0.1193(2) 0.12100(12) 0.0374(5) Uani 1 1 d . . . . .
H29A H 1.012454 0.084604 0.137825 0.045 Uiso 1 1 calc R U . . .
C30 C 0.7152(5) 0.0391(2) 0.09046(12) 0.0391(5) Uani 1 1 d . . . . .
H30A H 0.762549 -0.050171 0.086003 0.047 Uiso 1 1 calc R U . . .
C31 C 0.4977(4) 0.0907(2) 0.06653(11) 0.0367(5) Uani 1 1 d . . . . .
H31A H 0.394839 0.036444 0.045616 0.044 Uiso 1 1 calc R U . . .
C32 C 0.4289(4) 0.2208(2) 0.07284(10) 0.0311(5) Uani 1 1 d . . . . .
H32A H 0.278560 0.254755 0.056387 0.037 Uiso 1 1 calc R U . . .
C33 C 0.4344(4) 0.4432(2) 0.24572(12) 0.0392(5) Uani 1 1 d . . . . .
H33A H 0.343043 0.394478 0.216878 0.059 Uiso 1 1 calc R U . . .
H33B H 0.516714 0.381438 0.276023 0.059 Uiso 1 1 calc R U . . .
H33C H 0.323552 0.502243 0.267288 0.059 Uiso 1 1 calc R U . . .


_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
N1 C8 1.374(3) . ?
N1 C1 1.387(3) . ?
N1 C9 1.456(3) . ?
N2 C25 1.380(3) . ?
N2 C18 1.387(3) . ?
N2 C26 1.451(3) . ?
C1 C2 1.367(3) . ?
C1 C16 1.492(3) . ?
C2 C3 1.435(3) . ?
C2 C17 1.507(3) . ?
C3 C4 1.401(3) . ?
C3 C8 1.418(3) . ?
C4 C5 1.387(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.400(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.376(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7A 0.9500 . ?
C9 C10 1.516(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.380(4) . ?
C10 C11 1.385(3) . ?
C11 C12 1.387(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.376(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.374(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.390(4) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C19 1.509(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.367(3) . ?
C18 C33 1.496(3) . ?
C19 C20 1.436(3) . ?
C20 C21 1.407(3) . ?
C20 C25 1.417(3) . ?
C21 C22 1.379(4) . ?
C21 H21A 0.9500 . ?
C22 C23 1.402(4) . ?
C22 H22A 0.9500 . ?
C23 C24 1.386(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.394(3) . ?
C24 H24A 0.9500 . ?
C26 C27 1.517(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.386(3) . ?
C27 C32 1.393(3) . ?
C28 C29 1.395(3) . ?
C28 H28A 0.9500 . ?
C29 C30 1.385(4) . ?
C29 H29A 0.9500 . ?
C30 C31 1.383(4) . ?
C30 H30A 0.9500 . ?
C31 C32 1.383(3) . ?
C31 H31A 0.9500 . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

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 N1 C1 108.63(19) . . ?
C8 N1 C9 125.7(2) . . ?
C1 N1 C9 125.6(2) . . ?
C25 N2 C18 109.09(17) . . ?
C25 N2 C26 125.09(18) . . ?
C18 N2 C26 125.81(18) . . ?
C2 C1 N1 110.2(2) . . ?
C2 C1 C16 130.2(2) . . ?
N1 C1 C16 119.7(2) . . ?
C1 C2 C3 106.4(2) . . ?
C1 C2 C17 127.6(2) . . ?
C3 C2 C17 126.0(2) . . ?
C4 C3 C8 118.8(2) . . ?
C4 C3 C2 133.9(2) . . ?
C8 C3 C2 107.23(19) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 121.8(2) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C6 C7 C8 117.5(2) . . ?
C6 C7 H7A 121.2 . . ?
C8 C7 H7A 121.2 . . ?
N1 C8 C7 130.3(2) . . ?
N1 C8 C3 107.6(2) . . ?
C7 C8 C3 122.1(2) . . ?
N1 C9 C10 114.85(19) . . ?
N1 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C15 C10 C11 118.3(2) . . ?
C15 C10 C9 122.8(2) . . ?
C11 C10 C9 118.8(2) . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11A 119.5 . . ?
C12 C11 H11A 119.5 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C10 C15 C14 120.5(3) . . ?
C10 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C17 C19 113.82(18) . . ?
C2 C17 H17A 108.8 . . ?
C19 C17 H17A 108.8 . . ?
C2 C17 H17B 108.8 . . ?
C19 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 N2 109.52(19) . . ?
C19 C18 C33 129.5(2) . . ?
N2 C18 C33 121.0(2) . . ?
C18 C19 C20 107.01(19) . . ?
C18 C19 C17 127.0(2) . . ?
C20 C19 C17 126.03(19) . . ?
C21 C20 C25 118.4(2) . . ?
C21 C20 C19 134.4(2) . . ?
C25 C20 C19 107.14(18) . . ?
C22 C21 C20 119.1(2) . . ?
C22 C21 H21A 120.4 . . ?
C20 C21 H21A 120.4 . . ?
C21 C22 C23 121.3(2) . . ?
C21 C22 H22A 119.3 . . ?
C23 C22 H22A 119.3 . . ?
C24 C23 C22 121.3(2) . . ?
C24 C23 H23A 119.4 . . ?
C22 C23 H23A 119.4 . . ?
C23 C24 C25 117.3(2) . . ?
C23 C24 H24A 121.4 . . ?
C25 C24 H24A 121.4 . . ?
N2 C25 C24 130.2(2) . . ?
N2 C25 C20 107.24(19) . . ?
C24 C25 C20 122.6(2) . . ?
N2 C26 C27 114.51(17) . . ?
N2 C26 H26A 108.6 . . ?
C27 C26 H26A 108.6 . . ?
N2 C26 H26B 108.6 . . ?
C27 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C28 C27 C32 118.6(2) . . ?
C28 C27 C26 123.44(19) . . ?
C32 C27 C26 118.01(19) . . ?
C27 C28 C29 120.5(2) . . ?
C27 C28 H28A 119.8 . . ?
C29 C28 H28A 119.8 . . ?
C30 C29 C28 120.4(2) . . ?
C30 C29 H29A 119.8 . . ?
C28 C29 H29A 119.8 . . ?
C31 C30 C29 119.2(2) . . ?
C31 C30 H30A 120.4 . . ?
C29 C30 H30A 120.4 . . ?
C32 C31 C30 120.5(2) . . ?
C32 C31 H31A 119.8 . . ?
C30 C31 H31A 119.8 . . ?
C31 C32 C27 120.9(2) . . ?
C31 C32 H32A 119.5 . . ?
C27 C32 H32A 119.5 . . ?
C18 C33 H33A 109.5 . . ?
C18 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C18 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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 N1 C1 C2 0.7(3) . . . . ?
C9 N1 C1 C2 176.90(19) . . . . ?
C8 N1 C1 C16 -178.4(2) . . . . ?
C9 N1 C1 C16 -2.2(3) . . . . ?
N1 C1 C2 C3 0.0(2) . . . . ?
C16 C1 C2 C3 179.0(2) . . . . ?
N1 C1 C2 C17 -178.1(2) . . . . ?
C16 C1 C2 C17 0.9(4) . . . . ?
C1 C2 C3 C4 -178.3(2) . . . . ?
C17 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C8 -0.7(2) . . . . ?
C17 C2 C3 C8 177.49(19) . . . . ?
C8 C3 C4 C5 -0.6(3) . . . . ?
C2 C3 C4 C5 176.9(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C1 N1 C8 C7 176.7(2) . . . . ?
C9 N1 C8 C7 0.5(4) . . . . ?
C1 N1 C8 C3 -1.1(2) . . . . ?
C9 N1 C8 C3 -177.30(19) . . . . ?
C6 C7 C8 N1 -178.2(2) . . . . ?
C6 C7 C8 C3 -0.6(3) . . . . ?
C4 C3 C8 N1 179.16(18) . . . . ?
C2 C3 C8 N1 1.1(2) . . . . ?
C4 C3 C8 C7 1.1(3) . . . . ?
C2 C3 C8 C7 -176.96(19) . . . . ?
C8 N1 C9 C10 -110.4(3) . . . . ?
C1 N1 C9 C10 74.0(3) . . . . ?
N1 C9 C10 C15 22.5(4) . . . . ?
N1 C9 C10 C11 -159.6(2) . . . . ?
C15 C10 C11 C12 -0.7(4) . . . . ?
C9 C10 C11 C12 -178.6(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C11 C10 C15 C14 0.5(4) . . . . ?
C9 C10 C15 C14 178.4(3) . . . . ?
C13 C14 C15 C10 -0.2(5) . . . . ?
C1 C2 C17 C19 116.7(2) . . . . ?
C3 C2 C17 C19 -61.1(3) . . . . ?
C25 N2 C18 C19 0.6(2) . . . . ?
C26 N2 C18 C19 -178.92(19) . . . . ?
C25 N2 C18 C33 -179.49(19) . . . . ?
C26 N2 C18 C33 1.0(3) . . . . ?
N2 C18 C19 C20 -0.4(2) . . . . ?
C33 C18 C19 C20 179.7(2) . . . . ?
N2 C18 C19 C17 178.55(19) . . . . ?
C33 C18 C19 C17 -1.3(4) . . . . ?
C2 C17 C19 C18 -64.7(3) . . . . ?
C2 C17 C19 C20 114.1(2) . . . . ?
C18 C19 C20 C21 -178.4(2) . . . . ?
C17 C19 C20 C21 2.6(4) . . . . ?
C18 C19 C20 C25 0.1(2) . . . . ?
C17 C19 C20 C25 -178.9(2) . . . . ?
C25 C20 C21 C22 0.4(3) . . . . ?
C19 C20 C21 C22 178.8(2) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C18 N2 C25 C24 179.4(2) . . . . ?
C26 N2 C25 C24 -1.1(3) . . . . ?
C18 N2 C25 C20 -0.5(2) . . . . ?
C26 N2 C25 C20 179.01(18) . . . . ?
C23 C24 C25 N2 -179.5(2) . . . . ?
C23 C24 C25 C20 0.4(3) . . . . ?
C21 C20 C25 N2 179.05(18) . . . . ?
C19 C20 C25 N2 0.2(2) . . . . ?
C21 C20 C25 C24 -0.8(3) . . . . ?
C19 C20 C25 C24 -179.64(19) . . . . ?
C25 N2 C26 C27 96.5(2) . . . . ?
C18 N2 C26 C27 -84.0(3) . . . . ?
N2 C26 C27 C28 -8.5(3) . . . . ?
N2 C26 C27 C32 171.71(19) . . . . ?
C32 C27 C28 C29 0.5(3) . . . . ?
C26 C27 C28 C29 -179.4(2) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 -0.4(4) . . . . ?
C29 C30 C31 C32 0.2(4) . . . . ?
C30 C31 C32 C27 0.4(3) . . . . ?
C28 C27 C32 C31 -0.7(3) . . . . ?
C26 C27 C32 C31 179.1(2) . . . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_Compound3l
_database_code_depnum_ccdc_archive 'CCDC 2056481'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 F2 N2'
_chemical_formula_sum            'C21 H20 F2 N2'
_chemical_formula_weight         338.39

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'
F F 0.0727 0.0534 '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'

_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                   7.9071(6)
_cell_length_b                   8.9267(5)
_cell_length_c                   11.6792(7)
_cell_angle_alpha                86.424(5)
_cell_angle_beta                 84.971(6)
_cell_angle_gamma                85.252(6)
_cell_volume                     817.11(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2659
_cell_measurement_theta_min      3.7650
_cell_measurement_theta_max      72.4020

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.794
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            5413
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.805
_diffrn_reflns_theta_max         69.939
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3056
_reflns_number_gt                2619
_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0993P)²+0.7951P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0048(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3056
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1855
_refine_ls_wR_factor_gt          0.1768
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.207
_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
F1 F -0.0439(2) 0.34589(19) 0.64266(13) 0.0407(4) Uani 1 1 d . . . . .
F2 F 0.02819(19) 0.09854(19) 0.14554(14) 0.0395(4) Uani 1 1 d . . . . .
N1 N 0.6189(3) 0.1547(2) 0.53481(16) 0.0262(5) Uani 1 1 d . . . . .
N2 N 0.6411(3) 0.3226(2) 0.01890(16) 0.0248(5) Uani 1 1 d . . . . .
C1 C 0.6559(3) 0.2474(3) 0.43785(19) 0.0244(5) Uani 1 1 d . . . . .
C2 C 0.5125(3) 0.3363(3) 0.41163(19) 0.0228(5) Uani 1 1 d . . . . .
C3 C 0.3803(3) 0.2998(2) 0.49795(19) 0.0228(5) Uani 1 1 d . . . . .
C4 C 0.2108(3) 0.3553(3) 0.5209(2) 0.0259(5) Uani 1 1 d . . . . .
H4A H 0.159517 0.433456 0.473457 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1219(3) 0.2911(3) 0.6157(2) 0.0300(6) Uani 1 1 d . . . . .
C6 C 0.1871(3) 0.1746(3) 0.6876(2) 0.0318(6) Uani 1 1 d . . . . .
H6A H 0.117799 0.133805 0.750566 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3553(3) 0.1188(3) 0.6660(2) 0.0294(6) Uani 1 1 d . . . . .
H7A H 0.403617 0.038762 0.713163 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4511(3) 0.1839(3) 0.5730(2) 0.0247(5) Uani 1 1 d . . . . .
C9 C 0.7376(4) 0.0476(3) 0.5915(2) 0.0344(6) Uani 1 1 d . . . . .
H9A H 0.849576 0.046528 0.548205 0.052 Uiso 1 1 calc R U . . .
H9B H 0.747143 0.077270 0.669888 0.052 Uiso 1 1 calc R U . . .
H9C H 0.695980 -0.053058 0.594477 0.052 Uiso 1 1 calc R U . . .
C10 C 0.8297(3) 0.2430(3) 0.3777(2) 0.0317(6) Uani 1 1 d . . . . .
H10A H 0.904680 0.167563 0.417153 0.047 Uiso 1 1 calc R U . . .
H10B H 0.824751 0.216471 0.297949 0.047 Uiso 1 1 calc R U . . .
H10C H 0.874356 0.342136 0.378279 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4974(3) 0.4514(3) 0.31133(19) 0.0234(5) Uani 1 1 d . . . . .
H11A H 0.382627 0.505017 0.318732 0.028 Uiso 1 1 calc R U . . .
H11B H 0.581565 0.526486 0.316104 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6610(3) 0.4017(3) 0.11440(19) 0.0230(5) Uani 1 1 d . . . . .
C13 C 0.5252(3) 0.3861(2) 0.19450(19) 0.0216(5) Uani 1 1 d . . . . .
C14 C 0.4130(3) 0.2938(2) 0.14611(19) 0.0208(5) Uani 1 1 d . . . . .
C15 C 0.2537(3) 0.2408(3) 0.1840(2) 0.0242(5) Uani 1 1 d . . . . .
H15A H 0.197465 0.264660 0.256609 0.029 Uiso 1 1 calc R U . . .
C16 C 0.1831(3) 0.1528(3) 0.1110(2) 0.0279(6) Uani 1 1 d . . . . .
C17 C 0.2573(3) 0.1156(3) 0.0030(2) 0.0295(6) Uani 1 1 d . . . . .
H17A H 0.201550 0.055145 -0.043764 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4126(3) 0.1676(3) -0.0353(2) 0.0279(6) Uani 1 1 d . . . . .
H18A H 0.466172 0.143836 -0.108654 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4894(3) 0.2562(3) 0.03662(19) 0.0232(5) Uani 1 1 d . . . . .
C20 C 0.7588(3) 0.3097(3) -0.0841(2) 0.0321(6) Uani 1 1 d . . . . .
H20A H 0.857487 0.366775 -0.076380 0.048 Uiso 1 1 calc DR U . . .
H20B H 0.796896 0.203561 -0.093515 0.048 Uiso 1 1 calc R U . . .
H20C H 0.701092 0.350104 -0.151628 0.048 Uiso 1 1 calc R U . . .
C21 C 0.8150(3) 0.4893(3) 0.1180(2) 0.0290(6) Uani 1 1 d . . . . .
H21A H 0.888902 0.477286 0.046780 0.043 Uiso 1 1 calc DR U . . .
H21B H 0.778586 0.596135 0.125570 0.043 Uiso 1 1 calc R U . . .
H21C H 0.877738 0.451615 0.183990 0.043 Uiso 1 1 calc R U . . .


_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
F1 C5 1.377(3) . ?
F2 C16 1.373(3) . ?
N1 C8 1.371(3) . ?
N1 C1 1.385(3) . ?
N1 C9 1.454(3) . ?
N2 C19 1.375(3) . ?
N2 C12 1.384(3) . ?
N2 C20 1.460(3) . ?
C1 C2 1.375(3) . ?
C1 C10 1.486(3) . ?
C2 C3 1.430(3) . ?
C2 C11 1.515(3) . ?
C3 C4 1.399(3) . ?
C3 C8 1.424(3) . ?
C4 C5 1.378(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.390(4) . ?
C6 C7 1.388(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.394(3) . ?
C7 H7A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.508(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.371(3) . ?
C12 C21 1.506(3) . ?
C13 C14 1.433(3) . ?
C14 C15 1.408(3) . ?
C14 C19 1.413(3) . ?
C15 C16 1.376(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.392(4) . ?
C17 C18 1.377(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.397(3) . ?
C18 H18A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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 N1 C1 108.88(19) . . ?
C8 N1 C9 124.5(2) . . ?
C1 N1 C9 126.5(2) . . ?
C19 N2 C12 108.40(19) . . ?
C19 N2 C20 124.8(2) . . ?
C12 N2 C20 126.8(2) . . ?
C2 C1 N1 109.8(2) . . ?
C2 C1 C10 128.8(2) . . ?
N1 C1 C10 121.4(2) . . ?
C1 C2 C3 106.7(2) . . ?
C1 C2 C11 126.8(2) . . ?
C3 C2 C11 126.6(2) . . ?
C4 C3 C8 119.1(2) . . ?
C4 C3 C2 133.8(2) . . ?
C8 C3 C2 107.0(2) . . ?
C5 C4 C3 116.8(2) . . ?
C5 C4 H4A 121.6 . . ?
C3 C4 H4A 121.6 . . ?
F1 C5 C4 118.3(2) . . ?
F1 C5 C6 116.8(2) . . ?
C4 C5 C6 124.9(2) . . ?
C7 C6 C5 118.9(2) . . ?
C7 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
C6 C7 C8 117.9(2) . . ?
C6 C7 H7A 121.0 . . ?
C8 C7 H7A 121.0 . . ?
N1 C8 C7 130.1(2) . . ?
N1 C8 C3 107.6(2) . . ?
C7 C8 C3 122.3(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C2 114.42(19) . . ?
C13 C11 H11A 108.7 . . ?
C2 C11 H11A 108.7 . . ?
C13 C11 H11B 108.7 . . ?
C2 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 N2 110.1(2) . . ?
C13 C12 C21 129.7(2) . . ?
N2 C12 C21 120.2(2) . . ?
C12 C13 C14 106.5(2) . . ?
C12 C13 C11 127.5(2) . . ?
C14 C13 C11 126.0(2) . . ?
C15 C14 C19 119.0(2) . . ?
C15 C14 C13 134.0(2) . . ?
C19 C14 C13 107.0(2) . . ?
C16 C15 C14 116.9(2) . . ?
C16 C15 H15A 121.5 . . ?
C14 C15 H15A 121.5 . . ?
F2 C16 C15 118.4(2) . . ?
F2 C16 C17 117.1(2) . . ?
C15 C16 C17 124.5(2) . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 H17A 120.4 . . ?
C16 C17 H17A 120.4 . . ?
C17 C18 C19 118.2(2) . . ?
C17 C18 H18A 120.9 . . ?
C19 C18 H18A 120.9 . . ?
N2 C19 C18 129.8(2) . . ?
N2 C19 C14 107.9(2) . . ?
C18 C19 C14 122.3(2) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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 N1 C1 C2 -0.6(3) . . . . ?
C9 N1 C1 C2 -178.2(2) . . . . ?
C8 N1 C1 C10 179.1(2) . . . . ?
C9 N1 C1 C10 1.5(4) . . . . ?
N1 C1 C2 C3 1.3(2) . . . . ?
C10 C1 C2 C3 -178.4(2) . . . . ?
N1 C1 C2 C11 -179.1(2) . . . . ?
C10 C1 C2 C11 1.3(4) . . . . ?
C1 C2 C3 C4 176.8(2) . . . . ?
C11 C2 C3 C4 -2.8(4) . . . . ?
C1 C2 C3 C8 -1.6(2) . . . . ?
C11 C2 C3 C8 178.8(2) . . . . ?
C8 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 C5 -179.0(2) . . . . ?
C3 C4 C5 F1 178.23(19) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
F1 C5 C6 C7 -178.0(2) . . . . ?
C4 C5 C6 C7 1.6(4) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C1 N1 C8 C7 179.3(2) . . . . ?
C9 N1 C8 C7 -3.1(4) . . . . ?
C1 N1 C8 C3 -0.5(2) . . . . ?
C9 N1 C8 C3 177.2(2) . . . . ?
C6 C7 C8 N1 177.7(2) . . . . ?
C6 C7 C8 C3 -2.6(3) . . . . ?
C4 C3 C8 N1 -177.39(19) . . . . ?
C2 C3 C8 N1 1.2(2) . . . . ?
C4 C3 C8 C7 2.9(3) . . . . ?
C2 C3 C8 C7 -178.5(2) . . . . ?
C1 C2 C11 C13 63.9(3) . . . . ?
C3 C2 C11 C13 -116.5(2) . . . . ?
C19 N2 C12 C13 0.7(3) . . . . ?
C20 N2 C12 C13 -179.2(2) . . . . ?
C19 N2 C12 C21 -178.6(2) . . . . ?
C20 N2 C12 C21 1.5(3) . . . . ?
N2 C12 C13 C14 -0.7(2) . . . . ?
C21 C12 C13 C14 178.5(2) . . . . ?
N2 C12 C13 C11 178.9(2) . . . . ?
C21 C12 C13 C11 -1.9(4) . . . . ?
C2 C11 C13 C12 -109.7(3) . . . . ?
C2 C11 C13 C14 69.8(3) . . . . ?
C12 C13 C14 C15 -178.4(2) . . . . ?
C11 C13 C14 C15 1.9(4) . . . . ?
C12 C13 C14 C19 0.5(2) . . . . ?
C11 C13 C14 C19 -179.1(2) . . . . ?
C19 C14 C15 C16 0.8(3) . . . . ?
C13 C14 C15 C16 179.6(2) . . . . ?
C14 C15 C16 F2 179.7(2) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
F2 C16 C17 C18 180.0(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C12 N2 C19 C18 178.9(2) . . . . ?
C20 N2 C19 C18 -1.2(4) . . . . ?
C12 N2 C19 C14 -0.4(2) . . . . ?
C20 N2 C19 C14 179.6(2) . . . . ?
C17 C18 C19 N2 -179.3(2) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C15 C14 C19 N2 179.04(19) . . . . ?
C13 C14 C19 N2 -0.1(2) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C13 C14 C19 C18 -179.4(2) . . . . ?

_refine_diff_density_max         0.589
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.066

