# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_BOV1N
_audit_block_doi                 10.5517/ccdc.csd.cc21xkwf
_database_code_depnum_ccdc_archive 'CCDC 1904295'
loop_
_audit_author_name
_audit_author_address
'jiang peng'
;jilindaxue
China
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2019-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 Cl N O'
_chemical_formula_sum            'C19 H12 Cl N O'
_chemical_formula_weight         305.75
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.323(2)
_cell_length_b                   3.8319(3)
_cell_length_c                   31.479(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.288(4)
_cell_angle_gamma                90
_cell_volume                     2813.2(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8767
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      29.646
_cell_measurement_theta_min      3.115
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            17237
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.653
_diffrn_reflns_theta_min         3.116
_diffrn_ambient_temperature      149.25
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3383
_reflns_number_total             3978
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.228
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0289P)²+5.6123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1195
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.57643(2) -0.20509(15) 0.66172(2) 0.02789(14) Uani 1 1 d . . . . .
O1 O 0.59320(6) 0.3946(4) 0.49246(4) 0.0200(3) Uani 1 1 d . . . . .
N1 N 0.67743(7) 0.2846(5) 0.52645(5) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.57855(9) -0.0295(5) 0.61057(6) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.63180(8) 0.0354(5) 0.59284(6) 0.0197(4) Uani 1 1 d . . . . .
H2 H 0.6664 -0.0168 0.6075 0.024 Uiso 1 1 calc R . . . .
C3 C 0.63172(8) 0.1810(5) 0.55238(6) 0.0179(4) Uani 1 1 d . . . . .
C4 C 0.65270(8) 0.4040(5) 0.49219(6) 0.0188(4) Uani 1 1 d . . . . .
C5 C 0.68074(9) 0.5357(6) 0.45455(6) 0.0216(4) Uani 1 1 d . . . . .
H5 H 0.7214 0.5512 0.4546 0.026 Uiso 1 1 calc R . . . .
C6 C 0.65221(8) 0.6369(5) 0.41958(6) 0.0187(4) Uani 1 1 d . . . . .
H6 H 0.6115 0.6291 0.4206 0.022 Uiso 1 1 calc R . . . .
C7 C 0.67830(8) 0.7589(5) 0.37975(6) 0.0172(4) Uani 1 1 d . . . . .
C8 C 0.64711(8) 0.7358(5) 0.34036(5) 0.0157(3) Uani 1 1 d . . . . .
C9 C 0.59098(8) 0.5906(5) 0.33694(6) 0.0196(4) Uani 1 1 d . . . . .
H9 H 0.5729 0.4992 0.3615 0.023 Uiso 1 1 calc R . . . .
C10 C 0.56274(9) 0.5813(6) 0.29856(6) 0.0229(4) Uani 1 1 d . . . . .
H10 H 0.5253 0.4842 0.2970 0.027 Uiso 1 1 calc R . . . .
C11 C 0.58856(9) 0.7139(6) 0.26145(6) 0.0236(4) Uani 1 1 d . . . . .
H11 H 0.5683 0.7089 0.2352 0.028 Uiso 1 1 calc R . . . .
C12 C 0.52699(9) 0.0427(6) 0.58975(6) 0.0224(4) Uani 1 1 d . . . . .
H12 H 0.4916 -0.0055 0.6034 0.027 Uiso 1 1 calc R . . . .
C13 C 0.52710(9) 0.1857(6) 0.54892(6) 0.0234(4) Uani 1 1 d . . . . .
H13 H 0.4926 0.2347 0.5339 0.028 Uiso 1 1 calc R . . . .
C14 C 0.58024(8) 0.2514(5) 0.53163(6) 0.0180(4) Uani 1 1 d . . . . .
C15 C 0.73294(8) 0.8990(5) 0.37983(6) 0.0206(4) Uani 1 1 d . . . . .
H15 H 0.7531 0.9209 0.4060 0.025 Uiso 1 1 calc R . . . .
C16 C 0.75938(9) 1.0101(6) 0.34190(6) 0.0221(4) Uani 1 1 d . . . . .
H16 H 0.7976 1.0964 0.3426 0.026 Uiso 1 1 calc R . . . .
C17 C 0.73009(8) 0.9938(5) 0.30412(6) 0.0205(4) Uani 1 1 d . . . . .
H17 H 0.7480 1.0729 0.2788 0.025 Uiso 1 1 calc R . . . .
C18 C 0.67348(8) 0.8604(5) 0.30230(5) 0.0164(4) Uani 1 1 d . . . . .
C19 C 0.64262(9) 0.8493(5) 0.26330(6) 0.0200(4) Uani 1 1 d . . . . .
H19 H 0.6598 0.9373 0.2382 0.024 Uiso 1 1 calc R . . . .


_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 C1 1.7460(19) . ?
O1 C4 1.388(2) . ?
O1 C14 1.384(2) . ?
N1 C3 1.403(2) . ?
N1 C4 1.303(2) . ?
C1 C2 1.387(3) . ?
C1 C12 1.394(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(2) . ?
C3 C14 1.390(3) . ?
C4 C5 1.447(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.341(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.473(2) . ?
C7 C8 1.437(2) . ?
C7 C15 1.383(3) . ?
C8 C9 1.426(3) . ?
C8 C18 1.432(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.411(3) . ?
C11 H11 0.9500 . ?
C11 C19 1.364(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.397(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.412(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.370(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.417(3) . ?
C18 C19 1.421(3) . ?
C19 H19 0.9500 . ?

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
C14 O1 C4 103.81(14) . . ?
C4 N1 C3 104.25(16) . . ?
C2 C1 Cl1 118.02(15) . . ?
C2 C1 C12 123.18(17) . . ?
C12 C1 Cl1 118.79(15) . . ?
C1 C2 H2 121.8 . . ?
C1 C2 C3 116.32(18) . . ?
C3 C2 H2 121.8 . . ?
C2 C3 N1 130.45(18) . . ?
C14 C3 N1 109.18(16) . . ?
C14 C3 C2 120.36(18) . . ?
O1 C4 C5 118.04(16) . . ?
N1 C4 O1 115.09(16) . . ?
N1 C4 C5 126.86(18) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 C4 123.27(18) . . ?
C6 C5 H5 118.4 . . ?
C5 C6 H6 117.1 . . ?
C5 C6 C7 125.83(18) . . ?
C7 C6 H6 117.1 . . ?
C8 C7 C6 120.36(17) . . ?
C15 C7 C6 120.42(17) . . ?
C15 C7 C8 119.21(16) . . ?
C9 C8 C7 123.36(16) . . ?
C9 C8 C18 117.70(16) . . ?
C18 C8 C7 118.93(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.84(17) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.92(19) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.0 . . ?
C19 C11 C10 119.97(18) . . ?
C19 C11 H11 120.0 . . ?
C1 C12 H12 119.8 . . ?
C1 C12 C13 120.30(18) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 121.9 . . ?
C14 C13 C12 116.14(18) . . ?
C14 C13 H13 121.9 . . ?
O1 C14 C3 107.66(16) . . ?
C13 C14 O1 128.65(17) . . ?
C13 C14 C3 123.69(17) . . ?
C7 C15 H15 119.3 . . ?
C7 C15 C16 121.45(18) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.15(18) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.81(17) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C8 119.39(17) . . ?
C17 C18 C19 120.92(17) . . ?
C19 C18 C8 119.69(17) . . ?
C11 C19 C18 120.82(17) . . ?
C11 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?

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
Cl1 C1 C2 C3 -178.88(15) . . . . ?
Cl1 C1 C12 C13 179.54(17) . . . . ?
O1 C4 C5 C6 -2.4(3) . . . . ?
N1 C3 C14 O1 0.8(2) . . . . ?
N1 C3 C14 C13 -178.87(19) . . . . ?
N1 C4 C5 C6 176.3(2) . . . . ?
C1 C2 C3 N1 178.2(2) . . . . ?
C1 C2 C3 C14 -0.5(3) . . . . ?
C1 C12 C13 C14 -0.8(3) . . . . ?
C2 C1 C12 C13 0.4(3) . . . . ?
C2 C3 C14 O1 179.82(18) . . . . ?
C2 C3 C14 C13 0.1(3) . . . . ?
C3 N1 C4 O1 0.6(2) . . . . ?
C3 N1 C4 C5 -178.1(2) . . . . ?
C4 O1 C14 C3 -0.4(2) . . . . ?
C4 O1 C14 C13 179.2(2) . . . . ?
C4 N1 C3 C2 -179.7(2) . . . . ?
C4 N1 C3 C14 -0.9(2) . . . . ?
C4 C5 C6 C7 -177.29(19) . . . . ?
C5 C6 C7 C8 156.5(2) . . . . ?
C5 C6 C7 C15 -23.9(3) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C6 C7 C8 C18 179.32(17) . . . . ?
C6 C7 C15 C16 178.47(19) . . . . ?
C7 C8 C9 C10 178.8(2) . . . . ?
C7 C8 C18 C17 1.8(3) . . . . ?
C7 C8 C18 C19 -178.10(18) . . . . ?
C7 C15 C16 C17 2.7(3) . . . . ?
C8 C7 C15 C16 -1.9(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C8 C18 C19 C11 -1.5(3) . . . . ?
C9 C8 C18 C17 -177.53(18) . . . . ?
C9 C8 C18 C19 2.6(3) . . . . ?
C9 C10 C11 C19 0.9(3) . . . . ?
C10 C11 C19 C18 -0.3(3) . . . . ?
C12 C1 C2 C3 0.3(3) . . . . ?
C12 C13 C14 O1 -179.10(19) . . . . ?
C12 C13 C14 C3 0.5(3) . . . . ?
C14 O1 C4 N1 -0.1(2) . . . . ?
C14 O1 C4 C5 178.72(18) . . . . ?
C15 C7 C8 C9 178.96(19) . . . . ?
C15 C7 C8 C18 -0.3(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C8 -1.1(3) . . . . ?
C16 C17 C18 C19 178.79(19) . . . . ?
C17 C18 C19 C11 178.60(19) . . . . ?
C18 C8 C9 C10 -2.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_D-BOV1N
_audit_block_doi                 10.5517/ccdc.csd.cc21c6sf
_database_code_depnum_ccdc_archive 'CCDC 1887614'
loop_
_audit_author_name
_audit_author_address
'jiang peng'
;jilindaxue
China
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2019-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H24 Cl2 N2 O2'
_chemical_formula_sum            'C38 H24 Cl2 N2 O2'
_chemical_formula_weight         611.49
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8015(4)
_cell_length_b                   12.0723(6)
_cell_length_c                   12.9926(6)
_cell_angle_alpha                71.138(2)
_cell_angle_beta                 85.828(2)
_cell_angle_gamma                79.452(2)
_cell_volume                     1430.08(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.447
_cell_measurement_theta_min      2.813
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16340
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.813
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5450
_reflns_number_total             6516
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6516
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.182
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0214P)²+4.2748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1581
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9825(6)
 0.0175(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C18(H18)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C21(H21), C22(H22),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C32(H32), C33(H33), C34(H34),
  C35(H35), C36(H36), C37(H37), C38(H38)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 1.00499(11) 0.79063(8) -0.25103(7) 0.0435(3) Uani 1 1 d . . . . .
Cl2 Cl 0.40742(9) -0.09473(7) 0.83625(7) 0.02730(19) Uani 1 1 d . . . . .
O1 O 0.6986(2) 0.15158(18) 0.44862(17) 0.0198(4) Uani 1 1 d . . . . .
O2 O 0.6949(2) 0.72894(18) 0.15447(17) 0.0203(5) Uani 1 1 d . . . . .
N1 N 0.8320(3) 0.5632(2) 0.1381(2) 0.0178(5) Uani 1 1 d . . . . .
N2 N 0.5492(3) 0.2690(2) 0.5263(2) 0.0197(5) Uani 1 1 d . . . . .
C1 C 0.9074(3) 0.7750(3) -0.1310(3) 0.0239(7) Uani 1 1 d . . . . .
C2 C 0.9208(3) 0.6640(3) -0.0523(2) 0.0213(6) Uani 1 1 d . . . . .
H2 H 0.979442 0.596218 -0.062369 0.026 Uiso 1 1 calc R . . . .
C3 C 0.8428(3) 0.6586(3) 0.0423(2) 0.0166(6) Uani 1 1 d . . . . .
C4 C 0.7460(3) 0.6093(3) 0.1992(2) 0.0165(6) Uani 1 1 d . . . . .
C5 C 0.6945(3) 0.5544(3) 0.3101(2) 0.0170(6) Uani 1 1 d . . . . .
H5 H 0.669321 0.613717 0.349994 0.020 Uiso 1 1 calc R . . . .
C6 C 0.7917(3) 0.4407(3) 0.3789(2) 0.0179(6) Uani 1 1 d . . . . .
H6 H 0.879586 0.427284 0.337134 0.022 Uiso 1 1 calc R . . . .
C7 C 0.6849(3) 0.3639(3) 0.3606(2) 0.0164(6) Uani 1 1 d . . . . .
H7 H 0.717469 0.335795 0.297060 0.020 Uiso 1 1 calc R . . . .
C8 C 0.6386(3) 0.2642(3) 0.4495(2) 0.0174(6) Uani 1 1 d . . . . .
C9 C 0.5473(3) 0.1487(3) 0.5861(2) 0.0182(6) Uani 1 1 d . . . . .
C10 C 0.4710(3) 0.0981(3) 0.6788(3) 0.0202(6) Uani 1 1 d . . . . .
H10 H 0.406141 0.144792 0.712517 0.024 Uiso 1 1 calc R . . . .
C11 C 0.4961(3) -0.0248(3) 0.7185(2) 0.0210(6) Uani 1 1 d . . . . .
C12 C 0.5903(3) -0.0956(3) 0.6704(3) 0.0246(7) Uani 1 1 d . . . . .
H12 H 0.603780 -0.179555 0.701852 0.030 Uiso 1 1 calc R . . . .
C13 C 0.6647(3) -0.0448(3) 0.5769(3) 0.0240(7) Uani 1 1 d . . . . .
H13 H 0.728292 -0.091243 0.542146 0.029 Uiso 1 1 calc R . . . .
C14 C 0.6398(3) 0.0780(3) 0.5381(2) 0.0186(6) Uani 1 1 d . . . . .
C15 C 0.8212(4) 0.8760(3) -0.1196(3) 0.0262(7) Uani 1 1 d . . . . .
H15 H 0.816606 0.949544 -0.176424 0.031 Uiso 1 1 calc R . . . .
C16 C 0.7424(4) 0.8694(3) -0.0255(3) 0.0254(7) Uani 1 1 d . . . . .
H16 H 0.681792 0.936456 -0.015879 0.030 Uiso 1 1 calc R . . . .
C17 C 0.7573(3) 0.7590(3) 0.0535(2) 0.0180(6) Uani 1 1 d . . . . .
C18 C 0.5764(3) 0.4776(3) 0.3217(2) 0.0161(6) Uani 1 1 d . . . . .
H18 H 0.514175 0.485192 0.384373 0.019 Uiso 1 1 calc R . . . .
C19 C 0.4883(3) 0.4944(3) 0.2254(2) 0.0173(6) Uani 1 1 d . . . . .
C20 C 0.4009(3) 0.6051(3) 0.1774(2) 0.0177(6) Uani 1 1 d . . . . .
C21 C 0.3884(3) 0.7015(3) 0.2194(3) 0.0202(6) Uani 1 1 d . . . . .
H21 H 0.439452 0.692733 0.281768 0.024 Uiso 1 1 calc R . . . .
C22 C 0.3036(3) 0.8072(3) 0.1711(3) 0.0254(7) Uani 1 1 d . . . . .
H22 H 0.296623 0.870629 0.200533 0.031 Uiso 1 1 calc R . . . .
C23 C 0.2272(3) 0.8227(3) 0.0788(3) 0.0269(7) Uani 1 1 d . . . . .
H23 H 0.170780 0.897005 0.044982 0.032 Uiso 1 1 calc R . . . .
C24 C 0.2337(3) 0.7308(3) 0.0375(3) 0.0247(7) Uani 1 1 d . . . . .
H24 H 0.180647 0.741482 -0.024405 0.030 Uiso 1 1 calc R . . . .
C25 C 0.3192(3) 0.6195(3) 0.0864(2) 0.0204(6) Uani 1 1 d . . . . .
C26 C 0.3197(3) 0.5213(3) 0.0488(3) 0.0237(7) Uani 1 1 d . . . . .
H26 H 0.263855 0.529886 -0.010951 0.028 Uiso 1 1 calc R . . . .
C27 C 0.4003(3) 0.4145(3) 0.0983(3) 0.0253(7) Uani 1 1 d . . . . .
H27 H 0.397645 0.348379 0.074404 0.030 Uiso 1 1 calc R . . . .
C28 C 0.4877(3) 0.4015(3) 0.1850(3) 0.0201(6) Uani 1 1 d . . . . .
H28 H 0.546792 0.327794 0.215969 0.024 Uiso 1 1 calc R . . . .
C29 C 0.8259(3) 0.4332(3) 0.4931(2) 0.0220(7) Uani 1 1 d . . . . .
C30 C 0.9103(3) 0.3275(3) 0.5594(3) 0.0254(7) Uani 1 1 d . . . . .
C31 C 0.9511(3) 0.3229(4) 0.6640(3) 0.0310(8) Uani 1 1 d . . . . .
C32 C 0.9091(4) 0.4231(4) 0.7003(3) 0.0348(9) Uani 1 1 d . . . . .
H32 H 0.936945 0.420728 0.769588 0.042 Uiso 1 1 calc R . . . .
C33 C 0.8295(4) 0.5222(4) 0.6365(3) 0.0332(8) Uani 1 1 d . . . . .
H33 H 0.802328 0.589059 0.661333 0.040 Uiso 1 1 calc R . . . .
C34 C 0.7870(4) 0.5269(3) 0.5345(3) 0.0261(7) Uani 1 1 d . . . . .
H34 H 0.729427 0.596729 0.492152 0.031 Uiso 1 1 calc R . . . .
C35 C 1.0323(4) 0.2176(4) 0.7302(3) 0.0411(11) Uani 1 1 d . . . . .
H35 H 1.060632 0.214513 0.799623 0.049 Uiso 1 1 calc R . . . .
C36 C 1.0703(4) 0.1207(4) 0.6960(3) 0.0446(11) Uani 1 1 d . . . . .
H36 H 1.123262 0.050453 0.742140 0.053 Uiso 1 1 calc R . . . .
C37 C 1.0313(4) 0.1244(4) 0.5921(3) 0.0369(9) Uani 1 1 d . . . . .
H37 H 1.057807 0.056576 0.568590 0.044 Uiso 1 1 calc R . . . .
C38 C 0.9554(3) 0.2254(3) 0.5255(3) 0.0276(7) Uani 1 1 d . . . . .
H38 H 0.932162 0.227620 0.455062 0.033 Uiso 1 1 calc R . . . .


_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 C1 1.744(3) . ?
Cl2 C11 1.746(3) . ?
O1 C8 1.382(4) . ?
O1 C14 1.377(3) . ?
O2 C4 1.382(4) . ?
O2 C17 1.373(4) . ?
N1 C3 1.410(4) . ?
N1 C4 1.291(4) . ?
N2 C8 1.288(4) . ?
N2 C9 1.411(4) . ?
C1 C2 1.389(4) . ?
C1 C15 1.395(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(4) . ?
C3 C17 1.385(4) . ?
C4 C5 1.472(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.563(4) . ?
C5 C18 1.581(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.596(4) . ?
C6 C29 1.515(4) . ?
C7 H7 1.0000 . ?
C7 C8 1.488(4) . ?
C7 C18 1.538(4) . ?
C9 C10 1.394(4) . ?
C9 C14 1.386(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 C12 1.395(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(4) . ?
C18 H18 1.0000 . ?
C18 C19 1.510(4) . ?
C19 C20 1.425(4) . ?
C19 C28 1.385(4) . ?
C20 C21 1.419(4) . ?
C20 C25 1.423(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.372(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.403(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.371(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.422(4) . ?
C25 C26 1.420(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.366(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.415(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.436(5) . ?
C29 C34 1.386(5) . ?
C30 C31 1.427(5) . ?
C30 C38 1.425(5) . ?
C31 C32 1.418(6) . ?
C31 C35 1.418(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.356(6) . ?
C33 H33 0.9500 . ?
C33 C34 1.399(5) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C35 C36 1.362(7) . ?
C36 H36 0.9500 . ?
C36 C37 1.415(6) . ?
C37 H37 0.9500 . ?
C37 C38 1.367(5) . ?
C38 H38 0.9500 . ?

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
C14 O1 C8 103.6(2) . . ?
C17 O2 C4 103.8(2) . . ?
C4 N1 C3 104.3(2) . . ?
C8 N2 C9 103.9(3) . . ?
C2 C1 Cl1 118.6(2) . . ?
C2 C1 C15 123.8(3) . . ?
C15 C1 Cl1 117.5(2) . . ?
C1 C2 H2 122.2 . . ?
C1 C2 C3 115.5(3) . . ?
C3 C2 H2 122.2 . . ?
C2 C3 N1 131.0(3) . . ?
C17 C3 N1 108.4(3) . . ?
C17 C3 C2 120.5(3) . . ?
O2 C4 C5 114.7(3) . . ?
N1 C4 O2 115.3(3) . . ?
N1 C4 C5 130.0(3) . . ?
C4 C5 H5 111.4 . . ?
C4 C5 C6 114.8(2) . . ?
C4 C5 C18 116.9(2) . . ?
C6 C5 H5 111.4 . . ?
C6 C5 C18 89.2(2) . . ?
C18 C5 H5 111.4 . . ?
C5 C6 H6 109.6 . . ?
C5 C6 C7 88.1(2) . . ?
C7 C6 H6 109.6 . . ?
C29 C6 C5 117.9(3) . . ?
C29 C6 H6 109.6 . . ?
C29 C6 C7 120.2(2) . . ?
C6 C7 H7 109.0 . . ?
C8 C7 C6 122.9(2) . . ?
C8 C7 H7 109.0 . . ?
C8 C7 C18 115.8(2) . . ?
C18 C7 C6 89.6(2) . . ?
C18 C7 H7 109.0 . . ?
O1 C8 C7 115.5(2) . . ?
N2 C8 O1 115.9(3) . . ?
N2 C8 C7 128.6(3) . . ?
C10 C9 N2 130.4(3) . . ?
C14 C9 N2 108.8(3) . . ?
C14 C9 C10 120.7(3) . . ?
C9 C10 H10 122.2 . . ?
C11 C10 C9 115.6(3) . . ?
C11 C10 H10 122.2 . . ?
C10 C11 Cl2 118.3(2) . . ?
C10 C11 C12 123.5(3) . . ?
C12 C11 Cl2 118.2(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 122.3 . . ?
C14 C13 C12 115.5(3) . . ?
C14 C13 H13 122.3 . . ?
O1 C14 C9 107.8(3) . . ?
O1 C14 C13 128.2(3) . . ?
C13 C14 C9 123.9(3) . . ?
C1 C15 H15 119.9 . . ?
C16 C15 C1 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 122.1 . . ?
C17 C16 C15 115.9(3) . . ?
C17 C16 H16 122.1 . . ?
O2 C17 C3 108.2(2) . . ?
O2 C17 C16 127.8(3) . . ?
C16 C17 C3 124.0(3) . . ?
C5 C18 H18 108.9 . . ?
C7 C18 C5 89.5(2) . . ?
C7 C18 H18 108.9 . . ?
C19 C18 C5 120.4(2) . . ?
C19 C18 C7 118.6(2) . . ?
C19 C18 H18 108.9 . . ?
C20 C19 C18 120.2(3) . . ?
C28 C19 C18 120.6(3) . . ?
C28 C19 C20 119.1(3) . . ?
C21 C20 C19 122.3(3) . . ?
C21 C20 C25 118.2(3) . . ?
C25 C20 C19 119.4(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.7(3) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 119.3(3) . . ?
C26 C25 C20 119.5(3) . . ?
C26 C25 C24 121.1(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C19 C28 C27 121.1(3) . . ?
C19 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C6 118.9(3) . . ?
C34 C29 C6 123.0(3) . . ?
C34 C29 C30 118.0(3) . . ?
C31 C30 C29 119.3(3) . . ?
C38 C30 C29 122.8(3) . . ?
C38 C30 C31 117.9(3) . . ?
C32 C31 C30 119.5(3) . . ?
C32 C31 C35 121.3(3) . . ?
C35 C31 C30 119.2(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.4(3) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.5(4) . . ?
C34 C33 H33 119.7 . . ?
C29 C34 C33 122.3(3) . . ?
C29 C34 H34 118.9 . . ?
C33 C34 H34 118.9 . . ?
C31 C35 H35 119.4 . . ?
C36 C35 C31 121.2(4) . . ?
C36 C35 H35 119.4 . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.2(4) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.0(4) . . ?
C38 C37 H37 120.0 . . ?
C30 C38 H38 119.3 . . ?
C37 C38 C30 121.5(3) . . ?
C37 C38 H38 119.3 . . ?

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
Cl1 C1 C2 C3 178.4(2) . . . . ?
Cl1 C1 C15 C16 -179.3(3) . . . . ?
Cl2 C11 C12 C13 -179.5(3) . . . . ?
O2 C4 C5 C6 -155.5(2) . . . . ?
O2 C4 C5 C18 102.0(3) . . . . ?
N1 C3 C17 O2 0.8(3) . . . . ?
N1 C3 C17 C16 180.0(3) . . . . ?
N1 C4 C5 C6 24.0(4) . . . . ?
N1 C4 C5 C18 -78.6(4) . . . . ?
N2 C9 C10 C11 -178.8(3) . . . . ?
N2 C9 C14 O1 -0.7(3) . . . . ?
N2 C9 C14 C13 179.2(3) . . . . ?
C1 C2 C3 N1 -179.1(3) . . . . ?
C1 C2 C3 C17 0.8(5) . . . . ?
C1 C15 C16 C17 0.9(5) . . . . ?
C2 C1 C15 C16 -0.1(6) . . . . ?
C2 C3 C17 O2 -179.1(3) . . . . ?
C2 C3 C17 C16 0.1(5) . . . . ?
C3 N1 C4 O2 0.3(3) . . . . ?
C3 N1 C4 C5 -179.2(3) . . . . ?
C4 O2 C17 C3 -0.6(3) . . . . ?
C4 O2 C17 C16 -179.7(3) . . . . ?
C4 N1 C3 C2 179.2(3) . . . . ?
C4 N1 C3 C17 -0.6(3) . . . . ?
C4 C5 C6 C7 -105.4(3) . . . . ?
C4 C5 C6 C29 131.1(3) . . . . ?
C4 C5 C18 C7 102.9(3) . . . . ?
C4 C5 C18 C19 -20.4(4) . . . . ?
C5 C6 C7 C8 -135.4(3) . . . . ?
C5 C6 C7 C18 -14.5(2) . . . . ?
C5 C6 C29 C30 177.5(3) . . . . ?
C5 C6 C29 C34 -6.9(4) . . . . ?
C5 C18 C19 C20 -63.1(4) . . . . ?
C5 C18 C19 C28 119.1(3) . . . . ?
C6 C5 C18 C7 -14.6(2) . . . . ?
C6 C5 C18 C19 -138.0(3) . . . . ?
C6 C7 C8 O1 -103.6(3) . . . . ?
C6 C7 C8 N2 77.2(4) . . . . ?
C6 C7 C18 C5 14.3(2) . . . . ?
C6 C7 C18 C19 139.1(2) . . . . ?
C6 C29 C30 C31 175.6(3) . . . . ?
C6 C29 C30 C38 -4.7(4) . . . . ?
C6 C29 C34 C33 -174.3(3) . . . . ?
C7 C6 C29 C30 72.1(4) . . . . ?
C7 C6 C29 C34 -112.2(3) . . . . ?
C7 C18 C19 C20 -171.1(2) . . . . ?
C7 C18 C19 C28 11.2(4) . . . . ?
C8 O1 C14 C9 1.1(3) . . . . ?
C8 O1 C14 C13 -178.8(3) . . . . ?
C8 N2 C9 C10 179.6(3) . . . . ?
C8 N2 C9 C14 -0.1(3) . . . . ?
C8 C7 C18 C5 141.1(3) . . . . ?
C8 C7 C18 C19 -94.0(3) . . . . ?
C9 N2 C8 O1 0.9(3) . . . . ?
C9 N2 C8 C7 -179.9(3) . . . . ?
C9 C10 C11 Cl2 178.6(2) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C10 C9 C14 O1 179.6(3) . . . . ?
C10 C9 C14 C13 -0.5(5) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C12 C13 C14 O1 179.5(3) . . . . ?
C12 C13 C14 C9 -0.4(5) . . . . ?
C14 O1 C8 N2 -1.3(3) . . . . ?
C14 O1 C8 C7 179.4(2) . . . . ?
C14 C9 C10 C11 0.8(5) . . . . ?
C15 C1 C2 C3 -0.8(5) . . . . ?
C15 C16 C17 O2 178.1(3) . . . . ?
C15 C16 C17 C3 -0.9(5) . . . . ?
C17 O2 C4 N1 0.2(3) . . . . ?
C17 O2 C4 C5 179.7(2) . . . . ?
C18 C5 C6 C7 14.1(2) . . . . ?
C18 C5 C6 C29 -109.4(3) . . . . ?
C18 C7 C8 O1 148.8(3) . . . . ?
C18 C7 C8 N2 -30.4(4) . . . . ?
C18 C19 C20 C21 -2.5(4) . . . . ?
C18 C19 C20 C25 179.7(3) . . . . ?
C18 C19 C28 C27 176.8(3) . . . . ?
C19 C20 C21 C22 179.8(3) . . . . ?
C19 C20 C25 C24 -179.0(3) . . . . ?
C19 C20 C25 C26 3.7(4) . . . . ?
C20 C19 C28 C27 -1.0(4) . . . . ?
C20 C21 C22 C23 -0.1(5) . . . . ?
C20 C25 C26 C27 -1.3(5) . . . . ?
C21 C20 C25 C24 3.1(4) . . . . ?
C21 C20 C25 C26 -174.2(3) . . . . ?
C21 C22 C23 C24 1.7(5) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C23 C24 C25 C20 -1.6(5) . . . . ?
C23 C24 C25 C26 175.7(3) . . . . ?
C24 C25 C26 C27 -178.6(3) . . . . ?
C25 C20 C21 C22 -2.3(4) . . . . ?
C25 C26 C27 C28 -2.2(5) . . . . ?
C26 C27 C28 C19 3.4(5) . . . . ?
C28 C19 C20 C21 175.3(3) . . . . ?
C28 C19 C20 C25 -2.5(4) . . . . ?
C29 C6 C7 C8 -13.8(4) . . . . ?
C29 C6 C7 C18 107.0(3) . . . . ?
C29 C30 C31 C32 -0.8(4) . . . . ?
C29 C30 C31 C35 178.8(3) . . . . ?
C29 C30 C38 C37 -177.5(3) . . . . ?
C30 C29 C34 C33 1.4(5) . . . . ?
C30 C31 C32 C33 0.7(5) . . . . ?
C30 C31 C35 C36 -0.8(5) . . . . ?
C31 C30 C38 C37 2.2(5) . . . . ?
C31 C32 C33 C34 0.4(5) . . . . ?
C31 C35 C36 C37 1.2(6) . . . . ?
C32 C31 C35 C36 178.8(3) . . . . ?
C32 C33 C34 C29 -1.4(5) . . . . ?
C34 C29 C30 C31 -0.2(4) . . . . ?
C34 C29 C30 C38 179.4(3) . . . . ?
C35 C31 C32 C33 -178.8(3) . . . . ?
C35 C36 C37 C38 0.1(6) . . . . ?
C36 C37 C38 C30 -1.9(5) . . . . ?
C38 C30 C31 C32 179.5(3) . . . . ?
C38 C30 C31 C35 -0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9825(6)
2 0.0175(6)

####################################################################### 
# 
# 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_BOV1NM
_audit_block_doi                 10.5517/ccdc.csd.cc212vcc
_database_code_depnum_ccdc_archive 'CCDC 1879572'
loop_
_audit_author_name
_audit_author_address
'jiang peng'
;130012
China
;
_audit_update_record             
;
2018-11-17 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Cl N O2'
_chemical_formula_weight         335.77

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      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                   3.9720(3)
_cell_length_b                   12.2566(7)
_cell_length_c                   16.4309(11)
_cell_angle_alpha                79.392(4)
_cell_angle_beta                 86.478(4)
_cell_angle_gamma                84.244(4)
_cell_volume                     781.52(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4478
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.90

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.003
_exptl_crystal_size_min          0.002
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21180
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.779
_diffrn_reflns_theta_max         27.764
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3637
_reflns_number_gt                2484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.1076P] 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         3637
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Cl1 Cl -0.19819(16) 0.16263(5) 0.17874(3) 0.0606(2) Uani 1 1 d . . . . .
O1 O 0.2692(3) 0.17616(11) 0.50429(8) 0.0427(3) Uani 1 1 d . . . . .
O2 O 0.7273(4) 0.45964(11) 0.91342(8) 0.0472(4) Uani 1 1 d . . . . .
N1 N 0.0269(4) 0.33876(13) 0.43483(10) 0.0418(4) Uani 1 1 d . . . . .
C1 C 0.1675(5) 0.15588(16) 0.43006(11) 0.0380(4) Uani 1 1 d . . . . .
C2 C 0.2083(5) 0.05797(17) 0.39966(13) 0.0469(5) Uani 1 1 d . . . . .
H2 H 0.3085 -0.0076 0.4300 0.056 Uiso 1 1 calc R U . . .
C3 C 0.0916(5) 0.06247(17) 0.32132(13) 0.0469(5) Uani 1 1 d . . . . .
H3 H 0.1157 -0.0012 0.2975 0.056 Uiso 1 1 calc R U . . .
C4 C -0.0619(5) 0.16167(17) 0.27777(12) 0.0412(5) Uani 1 1 d . . . . .
C5 C -0.1058(5) 0.25919(16) 0.30932(11) 0.0396(4) Uani 1 1 d . . . . .
H5 H -0.2120 0.3243 0.2798 0.048 Uiso 1 1 calc R U . . .
C6 C 0.0171(5) 0.25531(15) 0.38776(11) 0.0354(4) Uani 1 1 d . . . . .
C7 C 0.1767(5) 0.28868(16) 0.50127(12) 0.0397(4) Uani 1 1 d . . . . .
C8 C 0.2530(5) 0.33672(17) 0.57111(12) 0.0433(5) Uani 1 1 d . . . . .
H8 H 0.2186 0.4138 0.5665 0.052 Uiso 1 1 calc R U . . .
C9 C 0.3697(5) 0.27782(17) 0.64183(12) 0.0407(4) Uani 1 1 d . . . . .
H9 H 0.3967 0.2007 0.6467 0.049 Uiso 1 1 calc R U . . .
C10 C 0.4589(5) 0.32491(16) 0.71270(11) 0.0367(4) Uani 1 1 d . . . . .
C11 C 0.5776(5) 0.42801(17) 0.70028(12) 0.0410(4) Uani 1 1 d . . . . .
H11 H 0.5955 0.4677 0.6465 0.049 Uiso 1 1 calc R U . . .
C12 C 0.6734(5) 0.47617(16) 0.76547(12) 0.0395(4) Uani 1 1 d . . . . .
H12 H 0.7548 0.5462 0.7545 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6465(5) 0.41976(15) 0.84543(11) 0.0371(4) Uani 1 1 d . . . . .
C14 C 0.5238(5) 0.31221(15) 0.86302(11) 0.0353(4) Uani 1 1 d . . . . .
C15 C 0.4897(5) 0.25288(17) 0.94534(12) 0.0445(5) Uani 1 1 d . . . . .
H15 H 0.5543 0.2838 0.9890 0.053 Uiso 1 1 calc R U . . .
C16 C 0.3640(6) 0.15149(18) 0.96152(13) 0.0516(5) Uani 1 1 d . . . . .
H16 H 0.3410 0.1139 1.0159 0.062 Uiso 1 1 calc R U . . .
C17 C 0.2691(6) 0.10371(18) 0.89610(14) 0.0522(5) Uani 1 1 d . . . . .
H17 H 0.1826 0.0345 0.9074 0.063 Uiso 1 1 calc R U . . .
C18 C 0.3023(5) 0.15769(17) 0.81616(13) 0.0442(5) Uani 1 1 d . . . . .
H18 H 0.2395 0.1241 0.7738 0.053 Uiso 1 1 calc R U . . .
C19 C 0.4300(4) 0.26372(15) 0.79590(11) 0.0352(4) Uani 1 1 d . . . . .
C20 C 0.8516(5) 0.56703(17) 0.89968(14) 0.0497(5) Uani 1 1 d . . . . .
H20C H 1.0558 0.5662 0.8653 0.075 Uiso 1 1 calc R U . . .
H20B H 0.8983 0.5857 0.9519 0.075 Uiso 1 1 calc R U . . .
H20A H 0.6845 0.6215 0.8727 0.075 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 C4 1.7437(19) . ?
O1 C1 1.380(2) . ?
O1 C7 1.384(2) . ?
O2 C13 1.366(2) . ?
O2 C20 1.426(2) . ?
N1 C7 1.297(2) . ?
N1 C6 1.396(2) . ?
C1 C2 1.374(3) . ?
C1 C6 1.385(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C5 C6 1.397(2) . ?
C5 H5 0.9300 . ?
C7 C8 1.443(3) . ?
C8 C9 1.333(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.468(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(3) . ?
C10 C19 1.437(3) . ?
C11 C12 1.403(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.425(3) . ?
C14 C15 1.418(3) . ?
C14 C19 1.430(2) . ?
C15 C16 1.361(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.402(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.417(3) . ?
C18 H18 0.9300 . ?
C20 H20C 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20A 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 103.91(14) . . ?
C13 O2 C20 117.37(15) . . ?
C7 N1 C6 104.30(16) . . ?
C2 C1 O1 128.46(17) . . ?
C2 C1 C6 124.12(17) . . ?
O1 C1 C6 107.40(16) . . ?
C1 C2 C3 116.18(18) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C2 C3 C4 120.62(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 122.75(18) . . ?
C5 C4 Cl1 118.75(15) . . ?
C3 C4 Cl1 118.50(15) . . ?
C4 C5 C6 116.72(17) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
C1 C6 N1 109.39(16) . . ?
C1 C6 C5 119.60(17) . . ?
N1 C6 C5 130.99(17) . . ?
N1 C7 O1 114.99(16) . . ?
N1 C7 C8 127.48(18) . . ?
O1 C7 C8 117.53(17) . . ?
C9 C8 C7 124.23(19) . . ?
C9 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
C8 C9 C10 125.25(19) . . ?
C8 C9 H9 117.4 . . ?
C10 C9 H9 117.4 . . ?
C11 C10 C19 118.66(16) . . ?
C11 C10 C9 120.18(17) . . ?
C19 C10 C9 121.15(17) . . ?
C10 C11 C12 122.65(18) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C13 C12 C11 119.81(18) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O2 C13 C12 124.58(17) . . ?
O2 C13 C14 114.82(16) . . ?
C12 C13 C14 120.60(16) . . ?
C15 C14 C13 121.60(17) . . ?
C15 C14 C19 119.41(17) . . ?
C13 C14 C19 118.98(16) . . ?
C16 C15 C14 121.05(19) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.75(19) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C14 117.23(17) . . ?
C18 C19 C10 123.46(17) . . ?
C14 C19 C10 119.28(16) . . ?
O2 C20 H20C 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
O2 C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
H20B C20 H20A 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
C7 O1 C1 C2 177.6(2) . . . . ?
C7 O1 C1 C6 -0.91(19) . . . . ?
O1 C1 C2 C3 -177.66(19) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 Cl1 179.08(16) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
Cl1 C4 C5 C6 -177.99(14) . . . . ?
C2 C1 C6 N1 -177.98(19) . . . . ?
O1 C1 C6 N1 0.6(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
O1 C1 C6 C5 179.06(16) . . . . ?
C7 N1 C6 C1 -0.1(2) . . . . ?
C7 N1 C6 C5 -178.2(2) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 N1 176.75(19) . . . . ?
C6 N1 C7 O1 -0.6(2) . . . . ?
C6 N1 C7 C8 179.93(19) . . . . ?
C1 O1 C7 N1 1.0(2) . . . . ?
C1 O1 C7 C8 -179.49(17) . . . . ?
N1 C7 C8 C9 171.3(2) . . . . ?
O1 C7 C8 C9 -8.2(3) . . . . ?
C7 C8 C9 C10 178.03(18) . . . . ?
C8 C9 C10 C11 -30.4(3) . . . . ?
C8 C9 C10 C19 150.67(19) . . . . ?
C19 C10 C11 C12 0.3(3) . . . . ?
C9 C10 C11 C12 -178.66(18) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C20 O2 C13 C12 -0.7(3) . . . . ?
C20 O2 C13 C14 180.00(16) . . . . ?
C11 C12 C13 O2 -178.89(17) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
O2 C13 C14 C15 0.1(3) . . . . ?
C12 C13 C14 C15 -179.17(17) . . . . ?
O2 C13 C14 C19 179.52(15) . . . . ?
C12 C13 C14 C19 0.2(3) . . . . ?
C13 C14 C15 C16 178.28(19) . . . . ?
C19 C14 C15 C16 -1.1(3) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C14 0.1(3) . . . . ?
C17 C18 C19 C10 -177.97(19) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
C13 C14 C19 C18 -178.68(17) . . . . ?
C15 C14 C19 C10 178.86(16) . . . . ?
C13 C14 C19 C10 -0.5(3) . . . . ?
C11 C10 C19 C18 178.33(18) . . . . ?
C9 C10 C19 C18 -2.8(3) . . . . ?
C11 C10 C19 C14 0.3(3) . . . . ?
C9 C10 C19 C14 179.21(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.93 2.64 3.546(2) 165.7 2_656

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_D-BOV1N_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc21dl68
_database_code_depnum_ccdc_archive 'CCDC 1888929'
loop_
_audit_author_name
_audit_author_address
'jiang peng'
;130012
China
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2019-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H24 Cl2 N2 O2'
_chemical_formula_sum            'C38 H24 Cl2 N2 O2'
_chemical_formula_weight         611.49
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2664(4)
_cell_length_b                   11.4804(4)
_cell_length_c                   13.9234(6)
_cell_angle_alpha                106.434(2)
_cell_angle_beta                 108.935(2)
_cell_angle_gamma                99.360(2)
_cell_volume                     1429.08(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.495
_cell_measurement_theta_min      2.909
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23947
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_min         2.910
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7428
_reflns_number_total             8704
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         8704
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.7480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C11(H11), C12(H12), C14(H14), C17(H17), C18(H18),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C33(H33),
  C34(H34), C36(H36), C37(H37), C38(H38)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 1.10042(3) 0.18934(3) 0.84266(3) 0.02163(7) Uani 1 1 d . . . . .
Cl2 Cl 0.11589(4) -0.18871(3) 0.48114(3) 0.02961(9) Uani 1 1 d . . . . .
O1 O 0.43566(9) 0.29453(8) 0.83255(7) 0.01659(17) Uani 1 1 d . . . . .
O2 O 0.73331(8) 0.47867(8) 0.97430(7) 0.01308(15) Uani 1 1 d . . . . .
N1 N 0.27847(11) 0.30321(9) 0.67854(9) 0.01586(19) Uani 1 1 d . . . . .
N2 N 0.72706(10) 0.45235(9) 0.80531(8) 0.01391(18) Uani 1 1 d . . . . .
C1 C 0.48994(14) 0.79973(14) 0.46921(11) 0.0234(3) Uani 1 1 d . . . . .
H1 H 0.4653 0.8136 0.4023 0.028 Uiso 1 1 calc R . . . .
C2 C 0.42774(13) 0.68219(13) 0.47142(10) 0.0204(2) Uani 1 1 d . . . . .
H2 H 0.3619 0.6168 0.4057 0.024 Uiso 1 1 calc R . . . .
C3 C 0.46181(12) 0.66171(11) 0.56789(9) 0.0154(2) Uani 1 1 d . . . . .
H3 H 0.4182 0.5822 0.5681 0.018 Uiso 1 1 calc R . . . .
C4 C 0.56112(11) 0.75721(10) 0.66759(9) 0.01238(19) Uani 1 1 d . . . . .
C5 C 0.60011(11) 0.73850(10) 0.76960(9) 0.01163(19) Uani 1 1 d . . . . .
C6 C 0.52957(11) 0.61350(10) 0.77040(9) 0.01121(19) Uani 1 1 d . . . . .
H6 H 0.5380 0.5463 0.7107 0.013 Uiso 1 1 calc R . . . .
C7 C 0.36783(11) 0.57706(10) 0.75770(9) 0.01183(19) Uani 1 1 d . . . . .
H7 H 0.3048 0.5166 0.6825 0.014 Uiso 1 1 calc R . . . .
C8 C 0.41309(11) 0.50414(10) 0.83665(9) 0.0128(2) Uani 1 1 d . . . . .
H8 H 0.3792 0.5265 0.8974 0.015 Uiso 1 1 calc R . . . .
C9 C 0.37121(12) 0.36562(11) 0.77657(10) 0.0139(2) Uani 1 1 d . . . . .
C10 C 0.37325(12) 0.17195(11) 0.75797(10) 0.0162(2) Uani 1 1 d . . . . .
C11 C 0.39925(14) 0.06135(12) 0.77010(12) 0.0216(2) Uani 1 1 d . . . . .
H11 H 0.4687 0.0611 0.8347 0.026 Uiso 1 1 calc R . . . .
C12 C 0.31737(14) -0.04947(12) 0.68177(12) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.3295 -0.1286 0.6856 0.027 Uiso 1 1 calc R . . . .
C13 C 0.98902(12) 0.27312(11) 0.88463(10) 0.0151(2) Uani 1 1 d . . . . .
C14 C 0.90533(12) 0.32183(11) 0.81412(10) 0.0155(2) Uani 1 1 d . . . . .
H14 H 0.9064 0.3103 0.7441 0.019 Uiso 1 1 calc R . . . .
C15 C 0.81976(11) 0.38867(10) 0.85278(9) 0.0128(2) Uani 1 1 d . . . . .
C16 C 0.82237(11) 0.40463(10) 0.95626(9) 0.01214(19) Uani 1 1 d . . . . .
C17 C 0.90459(12) 0.35624(11) 1.02661(10) 0.0149(2) Uani 1 1 d . . . . .
H17 H 0.9036 0.3686 1.0968 0.018 Uiso 1 1 calc R . . . .
C18 C 0.98907(12) 0.28805(11) 0.98794(10) 0.0148(2) Uani 1 1 d . . . . .
H18 H 1.0472 0.2514 1.0321 0.018 Uiso 1 1 calc R . . . .
C19 C 0.68129(11) 0.50183(10) 0.87931(9) 0.01179(19) Uani 1 1 d . . . . .
C20 C 0.57554(11) 0.57640(10) 0.87196(9) 0.01158(19) Uani 1 1 d . . . . .
H20 H 0.6086 0.6524 0.9400 0.014 Uiso 1 1 calc R . . . .
C21 C 0.30002(11) 0.67912(10) 0.79403(9) 0.01222(19) Uani 1 1 d . . . . .
C22 C 0.37620(12) 0.78703(11) 0.88521(10) 0.0155(2) Uani 1 1 d . . . . .
H22 H 0.4735 0.7963 0.9272 0.019 Uiso 1 1 calc R . . . .
C23 C 0.31353(13) 0.88388(11) 0.91784(10) 0.0169(2) Uani 1 1 d . . . . .
H23 H 0.3680 0.9561 0.9819 0.020 Uiso 1 1 calc R . . . .
C24 C 0.17439(13) 0.87401(11) 0.85744(10) 0.0166(2) Uani 1 1 d . . . . .
H24 H 0.1346 0.9417 0.8774 0.020 Uiso 1 1 calc R . . . .
C25 C 0.08940(12) 0.76381(11) 0.76554(10) 0.0146(2) Uani 1 1 d . . . . .
C26 C -0.05736(13) 0.75022(13) 0.70581(11) 0.0218(3) Uani 1 1 d . . . . .
H26 H -0.0966 0.8187 0.7243 0.026 Uiso 1 1 calc R . . . .
C27 C -0.14266(13) 0.63996(14) 0.62218(12) 0.0271(3) Uani 1 1 d . . . . .
H27 H -0.2403 0.6323 0.5825 0.033 Uiso 1 1 calc R . . . .
C28 C -0.08546(13) 0.53784(13) 0.59499(11) 0.0238(3) Uani 1 1 d . . . . .
H28 H -0.1461 0.4603 0.5387 0.029 Uiso 1 1 calc R . . . .
C29 C 0.05705(12) 0.54860(11) 0.64883(10) 0.0172(2) Uani 1 1 d . . . . .
H29 H 0.0937 0.4788 0.6284 0.021 Uiso 1 1 calc R . . . .
C30 C 0.15015(11) 0.66270(10) 0.73458(9) 0.01265(19) Uani 1 1 d . . . . .
C31 C 0.27556(12) 0.17641(11) 0.66373(10) 0.0156(2) Uani 1 1 d . . . . .
C32 C 0.21746(13) -0.04567(11) 0.58741(11) 0.0200(2) Uani 1 1 d . . . . .
C33 C 0.19450(13) 0.06580(11) 0.57484(11) 0.0192(2) Uani 1 1 d . . . . .
H33 H 0.1275 0.0666 0.5095 0.023 Uiso 1 1 calc R . . . .
C34 C 0.58606(14) 0.89408(13) 0.56364(11) 0.0213(2) Uani 1 1 d . . . . .
H34 H 0.6275 0.9730 0.5614 0.026 Uiso 1 1 calc R . . . .
C35 C 0.62450(12) 0.87564(11) 0.66444(10) 0.0156(2) Uani 1 1 d . . . . .
C36 C 0.72569(13) 0.97205(11) 0.76223(11) 0.0182(2) Uani 1 1 d . . . . .
H36 H 0.7673 1.0515 0.7609 0.022 Uiso 1 1 calc R . . . .
C37 C 0.76386(13) 0.95148(11) 0.85840(10) 0.0181(2) Uani 1 1 d . . . . .
H37 H 0.8331 1.0161 0.9231 0.022 Uiso 1 1 calc R . . . .
C38 C 0.70057(12) 0.83418(11) 0.86200(9) 0.0151(2) Uani 1 1 d . . . . .
H38 H 0.7280 0.8214 0.9295 0.018 Uiso 1 1 calc R . . . .


_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 C13 1.7459(11) . ?
Cl2 C32 1.7436(13) . ?
O1 C9 1.3829(13) . ?
O1 C10 1.3846(14) . ?
O2 C16 1.3794(13) . ?
O2 C19 1.3755(13) . ?
N1 C9 1.2900(15) . ?
N1 C31 1.4051(14) . ?
N2 C15 1.4030(14) . ?
N2 C19 1.2942(14) . ?
C1 H1 0.9500 . ?
C1 C2 1.4091(19) . ?
C1 C34 1.371(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.3720(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.4231(16) . ?
C4 C5 1.4337(16) . ?
C4 C35 1.4277(16) . ?
C5 C6 1.5034(15) . ?
C5 C38 1.3771(15) . ?
C6 H6 1.0000 . ?
C6 C7 1.5828(15) . ?
C6 C20 1.5416(15) . ?
C7 H7 1.0000 . ?
C7 C8 1.5623(15) . ?
C7 C21 1.5073(15) . ?
C8 H8 1.0000 . ?
C8 C9 1.4850(16) . ?
C8 C20 1.5807(15) . ?
C10 C11 1.3837(16) . ?
C10 C31 1.3896(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3906(19) . ?
C12 H12 0.9500 . ?
C12 C32 1.397(2) . ?
C13 C14 1.3907(16) . ?
C13 C18 1.3995(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3938(15) . ?
C15 C16 1.3908(16) . ?
C16 C17 1.3799(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.3929(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.4839(14) . ?
C20 H20 1.0000 . ?
C21 C22 1.3815(16) . ?
C21 C30 1.4419(14) . ?
C22 H22 0.9500 . ?
C22 C23 1.4118(15) . ?
C23 H23 0.9500 . ?
C23 C24 1.3691(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.4140(16) . ?
C25 C26 1.4222(16) . ?
C25 C30 1.4315(15) . ?
C26 H26 0.9500 . ?
C26 C27 1.3670(19) . ?
C27 H27 0.9500 . ?
C27 C28 1.4070(18) . ?
C28 H28 0.9500 . ?
C28 C29 1.3764(16) . ?
C29 H29 0.9500 . ?
C29 C30 1.4220(16) . ?
C31 C33 1.3912(17) . ?
C32 C33 1.3863(17) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.4164(17) . ?
C35 C36 1.4189(17) . ?
C36 H36 0.9500 . ?
C36 C37 1.3678(18) . ?
C37 H37 0.9500 . ?
C37 C38 1.4189(16) . ?
C38 H38 0.9500 . ?

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 O1 C10 103.20(9) . . ?
C19 O2 C16 103.59(8) . . ?
C9 N1 C31 104.15(10) . . ?
C19 N2 C15 103.89(9) . . ?
C2 C1 H1 120.0 . . ?
C34 C1 H1 120.0 . . ?
C34 C1 C2 120.03(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.36(12) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.28(11) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 122.69(10) . . ?
C3 C4 C35 117.97(10) . . ?
C35 C4 C5 119.33(10) . . ?
C4 C5 C6 118.00(9) . . ?
C38 C5 C4 119.20(10) . . ?
C38 C5 C6 122.79(10) . . ?
C5 C6 H6 106.8 . . ?
C5 C6 C7 121.92(9) . . ?
C5 C6 C20 122.67(9) . . ?
C7 C6 H6 106.8 . . ?
C20 C6 H6 106.8 . . ?
C20 C6 C7 90.08(8) . . ?
C6 C7 H7 110.6 . . ?
C8 C7 C6 87.61(8) . . ?
C8 C7 H7 110.6 . . ?
C21 C7 C6 120.10(9) . . ?
C21 C7 H7 110.6 . . ?
C21 C7 C8 115.24(9) . . ?
C7 C8 H8 112.7 . . ?
C7 C8 C20 89.41(8) . . ?
C9 C8 C7 111.48(9) . . ?
C9 C8 H8 112.7 . . ?
C9 C8 C20 115.74(9) . . ?
C20 C8 H8 112.7 . . ?
O1 C9 C8 116.66(10) . . ?
N1 C9 O1 115.99(10) . . ?
N1 C9 C8 127.33(10) . . ?
O1 C10 C31 107.88(10) . . ?
C11 C10 O1 128.34(11) . . ?
C11 C10 C31 123.78(12) . . ?
C10 C11 H11 122.1 . . ?
C10 C11 C12 115.77(12) . . ?
C12 C11 H11 122.1 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C32 120.67(11) . . ?
C32 C12 H12 119.7 . . ?
C14 C13 Cl1 118.50(9) . . ?
C14 C13 C18 123.40(10) . . ?
C18 C13 Cl1 118.09(9) . . ?
C13 C14 H14 122.1 . . ?
C13 C14 C15 115.70(11) . . ?
C15 C14 H14 122.1 . . ?
C14 C15 N2 130.67(11) . . ?
C16 C15 N2 108.89(9) . . ?
C16 C15 C14 120.39(10) . . ?
O2 C16 C15 107.67(9) . . ?
O2 C16 C17 127.99(10) . . ?
C17 C16 C15 124.31(10) . . ?
C16 C17 H17 122.2 . . ?
C16 C17 C18 115.57(11) . . ?
C18 C17 H17 122.2 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.61(10) . . ?
C17 C18 H18 119.7 . . ?
O2 C19 C20 116.43(9) . . ?
N2 C19 O2 115.95(9) . . ?
N2 C19 C20 127.57(10) . . ?
C6 C20 C8 88.41(8) . . ?
C6 C20 H20 110.9 . . ?
C8 C20 H20 110.9 . . ?
C19 C20 C6 116.02(9) . . ?
C19 C20 C8 118.05(9) . . ?
C19 C20 H20 110.9 . . ?
C22 C21 C7 121.91(10) . . ?
C22 C21 C30 118.55(10) . . ?
C30 C21 C7 119.50(10) . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C23 121.89(10) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.18(11) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.50(10) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 120.77(10) . . ?
C24 C25 C30 119.67(10) . . ?
C26 C25 C30 119.52(11) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.89(11) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.84(11) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 120.96(12) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 120.91(11) . . ?
C30 C29 H29 119.5 . . ?
C25 C30 C21 118.91(10) . . ?
C29 C30 C21 123.30(10) . . ?
C29 C30 C25 117.74(10) . . ?
C10 C31 N1 108.77(10) . . ?
C10 C31 C33 120.55(11) . . ?
C33 C31 N1 130.67(11) . . ?
C12 C32 Cl2 118.07(9) . . ?
C33 C32 Cl2 118.69(10) . . ?
C33 C32 C12 123.23(12) . . ?
C31 C33 H33 122.0 . . ?
C32 C33 C31 115.97(12) . . ?
C32 C33 H33 122.0 . . ?
C1 C34 H34 119.5 . . ?
C1 C34 C35 121.02(12) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 C4 119.33(11) . . ?
C34 C35 C36 121.36(11) . . ?
C36 C35 C4 119.31(11) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.51(11) . . ?
C37 C36 H36 119.7 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.36(11) . . ?
C38 C37 H37 119.8 . . ?
C5 C38 C37 121.26(11) . . ?
C5 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O2 1.00 2.43 3.4054(14) 164.9 2_667
C14 H14 Cl2 0.95 2.96 3.8780(12) 161.7 2_656

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
Cl1 C13 C14 C15 -179.45(8) . . . . ?
Cl1 C13 C18 C17 178.66(9) . . . . ?
Cl2 C32 C33 C31 178.03(9) . . . . ?
O1 C10 C11 C12 178.39(11) . . . . ?
O1 C10 C31 N1 1.05(13) . . . . ?
O1 C10 C31 C33 -178.90(10) . . . . ?
O2 C16 C17 C18 -177.65(10) . . . . ?
O2 C19 C20 C6 173.97(9) . . . . ?
O2 C19 C20 C8 -83.01(12) . . . . ?
N1 C31 C33 C32 -179.60(12) . . . . ?
N2 C15 C16 O2 -0.58(12) . . . . ?
N2 C15 C16 C17 -178.83(11) . . . . ?
N2 C19 C20 C6 -8.47(16) . . . . ?
N2 C19 C20 C8 94.55(14) . . . . ?
C1 C2 C3 C4 -0.62(18) . . . . ?
C1 C34 C35 C4 -0.49(18) . . . . ?
C1 C34 C35 C36 178.93(11) . . . . ?
C2 C1 C34 C35 -0.02(19) . . . . ?
C2 C3 C4 C5 -179.38(11) . . . . ?
C2 C3 C4 C35 0.10(16) . . . . ?
C3 C4 C5 C6 -1.55(15) . . . . ?
C3 C4 C5 C38 177.90(10) . . . . ?
C3 C4 C35 C34 0.45(16) . . . . ?
C3 C4 C35 C36 -178.98(10) . . . . ?
C4 C5 C6 C7 -73.80(13) . . . . ?
C4 C5 C6 C20 172.54(9) . . . . ?
C4 C5 C38 C37 1.25(16) . . . . ?
C4 C35 C36 C37 0.89(17) . . . . ?
C5 C4 C35 C34 179.94(10) . . . . ?
C5 C4 C35 C36 0.51(15) . . . . ?
C5 C6 C7 C8 -145.64(10) . . . . ?
C5 C6 C7 C21 -27.65(15) . . . . ?
C5 C6 C20 C8 144.86(10) . . . . ?
C5 C6 C20 C19 -94.48(12) . . . . ?
C6 C5 C38 C37 -179.32(10) . . . . ?
C6 C7 C8 C9 -101.89(9) . . . . ?
C6 C7 C8 C20 15.67(8) . . . . ?
C6 C7 C21 C22 -36.43(16) . . . . ?
C6 C7 C21 C30 145.68(10) . . . . ?
C7 C6 C20 C8 15.88(8) . . . . ?
C7 C6 C20 C19 136.54(9) . . . . ?
C7 C8 C9 O1 164.24(9) . . . . ?
C7 C8 C9 N1 -17.66(15) . . . . ?
C7 C8 C20 C6 -16.09(8) . . . . ?
C7 C8 C20 C19 -134.94(10) . . . . ?
C7 C21 C22 C23 178.58(11) . . . . ?
C7 C21 C30 C25 -175.93(10) . . . . ?
C7 C21 C30 C29 6.69(17) . . . . ?
C8 C7 C21 C22 66.29(14) . . . . ?
C8 C7 C21 C30 -111.60(11) . . . . ?
C9 O1 C10 C11 179.13(12) . . . . ?
C9 O1 C10 C31 -0.66(12) . . . . ?
C9 N1 C31 C10 -0.99(13) . . . . ?
C9 N1 C31 C33 178.95(12) . . . . ?
C9 C8 C20 C6 97.59(10) . . . . ?
C9 C8 C20 C19 -21.27(14) . . . . ?
C10 O1 C9 N1 0.03(13) . . . . ?
C10 O1 C9 C8 178.35(9) . . . . ?
C10 C11 C12 C32 0.82(18) . . . . ?
C10 C31 C33 C32 0.33(17) . . . . ?
C11 C10 C31 N1 -178.76(11) . . . . ?
C11 C10 C31 C33 1.30(19) . . . . ?
C11 C12 C32 Cl2 -178.61(10) . . . . ?
C11 C12 C32 C33 0.8(2) . . . . ?
C12 C32 C33 C31 -1.32(18) . . . . ?
C13 C14 C15 N2 177.95(11) . . . . ?
C13 C14 C15 C16 0.68(16) . . . . ?
C14 C13 C18 C17 -1.13(18) . . . . ?
C14 C15 C16 O2 177.23(10) . . . . ?
C14 C15 C16 C17 -1.02(17) . . . . ?
C15 N2 C19 O2 -0.03(13) . . . . ?
C15 N2 C19 C20 -177.60(11) . . . . ?
C15 C16 C17 C18 0.24(17) . . . . ?
C16 O2 C19 N2 -0.32(12) . . . . ?
C16 O2 C19 C20 177.53(9) . . . . ?
C16 C17 C18 C13 0.80(16) . . . . ?
C18 C13 C14 C15 0.35(17) . . . . ?
C19 O2 C16 C15 0.53(11) . . . . ?
C19 O2 C16 C17 178.70(11) . . . . ?
C19 N2 C15 C14 -177.14(12) . . . . ?
C19 N2 C15 C16 0.37(12) . . . . ?
C20 C6 C7 C8 -16.08(8) . . . . ?
C20 C6 C7 C21 101.91(10) . . . . ?
C20 C8 C9 O1 64.02(13) . . . . ?
C20 C8 C9 N1 -117.88(12) . . . . ?
C21 C7 C8 C9 135.75(9) . . . . ?
C21 C7 C8 C20 -106.69(9) . . . . ?
C21 C22 C23 C24 -1.44(19) . . . . ?
C22 C21 C30 C25 6.10(16) . . . . ?
C22 C21 C30 C29 -171.27(11) . . . . ?
C22 C23 C24 C25 3.71(18) . . . . ?
C23 C24 C25 C26 176.70(12) . . . . ?
C23 C24 C25 C30 -0.96(18) . . . . ?
C24 C25 C26 C27 -174.90(13) . . . . ?
C24 C25 C30 C21 -3.96(16) . . . . ?
C24 C25 C30 C29 173.57(11) . . . . ?
C25 C26 C27 C28 0.5(2) . . . . ?
C26 C25 C30 C21 178.35(11) . . . . ?
C26 C25 C30 C29 -4.12(17) . . . . ?
C26 C27 C28 C29 -2.4(2) . . . . ?
C27 C28 C29 C30 0.9(2) . . . . ?
C28 C29 C30 C21 179.74(12) . . . . ?
C28 C29 C30 C25 2.33(18) . . . . ?
C30 C21 C22 C23 -3.51(17) . . . . ?
C30 C25 C26 C27 2.77(19) . . . . ?
C31 N1 C9 O1 0.60(13) . . . . ?
C31 N1 C9 C8 -177.51(11) . . . . ?
C31 C10 C11 C12 -1.84(19) . . . . ?
C34 C1 C2 C3 0.59(19) . . . . ?
C34 C35 C36 C37 -178.53(11) . . . . ?
C35 C4 C5 C6 178.99(9) . . . . ?
C35 C4 C5 C38 -1.56(15) . . . . ?
C35 C36 C37 C38 -1.24(18) . . . . ?
C36 C37 C38 C5 0.15(18) . . . . ?
C38 C5 C6 C7 106.78(12) . . . . ?
C38 C5 C6 C20 -6.89(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
