# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1900703'
loop_
_audit_author_name
_audit_author_address
'Zhonghua Li'
;Tianjin University
China
;

_audit_update_record             
;
2019-03-03 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2017-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 Cl2 N2 O'
_chemical_formula_sum            'C18 H12 Cl2 N2 O'
_chemical_formula_weight         343.20
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.756(3)
_cell_length_b                   11.5471(19)
_cell_length_c                   18.635(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.357(4)
_cell_angle_gamma                90
_cell_volume                     3172.5(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4260
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.9520
_exptl_absorpt_correction_T_min  0.9218
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31197
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         3.092
_diffrn_ambient_temperature      133.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4497
_reflns_number_total             7185
_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       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7185
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      0.954
_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)+(0.0389P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0881
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N1-H19 = N1'-H19'
 0.9 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C1'(H1'), C2'(H2'), C4'(H4'), C5'(H5'), C8'(H8'), C9'(H9'),
  C10'(H10'), C11'(H11'), C16'(H16'), C17'(H17'), C18'(H18')
;
_atom_sites_solution_hydrogens   mixed
_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 0.61836(4) 0.62790(4) 0.21921(3) 0.03527(15) Uani 1 1 d . . . . .
Cl2 Cl 0.86992(4) 0.40342(4) 0.30346(3) 0.03553(15) Uani 1 1 d . . . . .
Cl1' Cl 0.68005(4) -0.36896(4) 0.40503(3) 0.03976(15) Uani 1 1 d . . . . .
Cl2' Cl 1.03288(4) 0.37653(5) 0.47097(4) 0.05175(19) Uani 1 1 d . . . . .
O1 O 0.82836(9) 0.13466(11) 0.28245(7) 0.0228(3) Uani 1 1 d . . . . .
O1' O 0.87208(10) 0.23253(13) 0.53466(8) 0.0351(4) Uani 1 1 d . . . . .
N1 N 0.82646(10) 0.14212(13) 0.16126(9) 0.0191(4) Uani 1 1 d D . . . .
H19 H 0.8484(12) 0.1725(16) 0.1221(7) 0.023 Uiso 1 1 d DR . . . .
N2 N 1.03796(11) 0.39935(14) 0.26623(9) 0.0280(4) Uani 1 1 d . . . . .
N1' N 0.80236(11) 0.19380(13) 0.42634(9) 0.0204(4) Uani 1 1 d D . . . .
H19' H 0.8097(13) 0.1696(16) 0.3817(6) 0.024 Uiso 1 1 d DR . . . .
N2' N 1.11387(12) 0.21076(17) 0.40632(10) 0.0360(5) Uani 1 1 d . . . . .
C1 C 0.66921(13) 0.32044(17) 0.13419(11) 0.0239(5) Uani 1 1 d . . . . .
H1 H 0.688520 0.292360 0.089395 0.029 Uiso 1 1 calc R . . . .
C2 C 0.65742(13) 0.43816(17) 0.14373(11) 0.0243(5) Uani 1 1 d . . . . .
H2 H 0.666552 0.490467 0.105348 0.029 Uiso 1 1 calc R . . . .
C3 C 0.63246(13) 0.47844(16) 0.20900(11) 0.0223(5) Uani 1 1 d . . . . .
C4 C 0.61792(13) 0.40412(17) 0.26540(11) 0.0233(5) Uani 1 1 d . . . . .
H4 H 0.601446 0.433301 0.310708 0.028 Uiso 1 1 calc R . . . .
C5 C 0.62786(12) 0.28563(17) 0.25460(11) 0.0222(4) Uani 1 1 d . . . . .
H5 H 0.617040 0.233545 0.292772 0.027 Uiso 1 1 calc R . . . .
C6 C 0.65325(12) 0.24254(16) 0.18915(11) 0.0189(4) Uani 1 1 d . . . . .
C7 C 0.66324(13) 0.11652(16) 0.17404(10) 0.0194(4) Uani 1 1 d . . . . .
C8 C 0.58921(13) 0.04148(17) 0.17396(11) 0.0257(5) Uani 1 1 d . . . . .
H8 H 0.532378 0.068817 0.189132 0.031 Uiso 1 1 calc R . . . .
C9 C 0.59766(14) -0.07304(17) 0.15188(12) 0.0296(5) Uani 1 1 d . . . . .
H9 H 0.546852 -0.123483 0.152699 0.035 Uiso 1 1 calc R . . . .
C10 C 0.67914(14) -0.11352(17) 0.12891(12) 0.0276(5) Uani 1 1 d . . . . .
H10 H 0.683865 -0.190716 0.111842 0.033 Uiso 1 1 calc R . . . .
C11 C 0.75430(13) -0.04171(16) 0.13067(11) 0.0226(5) Uani 1 1 d . . . . .
H11 H 0.811029 -0.069963 0.115854 0.027 Uiso 1 1 calc R . . . .
C12 C 0.74646(12) 0.07137(16) 0.15410(10) 0.0185(4) Uani 1 1 d . . . . .
C13 C 0.86184(12) 0.16693(15) 0.22660(11) 0.0183(4) Uani 1 1 d . . . . .
C14 C 0.94925(13) 0.23438(16) 0.22688(10) 0.0194(4) Uani 1 1 d . . . . .
C15 C 0.96170(13) 0.33916(17) 0.26291(11) 0.0239(5) Uani 1 1 d . . . . .
C16 C 1.10805(14) 0.35522(18) 0.23202(12) 0.0303(5) Uani 1 1 d . . . . .
H16 H 1.163725 0.396646 0.234006 0.036 Uiso 1 1 calc R . . . .
C17 C 1.10371(14) 0.25305(18) 0.19415(12) 0.0311(5) Uani 1 1 d . . . . .
H17 H 1.154972 0.225082 0.170259 0.037 Uiso 1 1 calc R . . . .
C18 C 1.02290(13) 0.19179(17) 0.19162(11) 0.0264(5) Uani 1 1 d . . . . .
H18 H 1.018108 0.120956 0.165812 0.032 Uiso 1 1 calc R . . . .
C1' C 0.72540(13) -0.04309(17) 0.46563(11) 0.0244(5) Uani 1 1 d . . . . .
H1' H 0.767206 -0.003462 0.497023 0.029 Uiso 1 1 calc R . . . .
C2' C 0.73255(14) -0.16211(17) 0.45765(11) 0.0264(5) Uani 1 1 d . . . . .
H2' H 0.778360 -0.204205 0.483735 0.032 Uiso 1 1 calc R . . . .
C3' C 0.67220(14) -0.21832(17) 0.41129(12) 0.0267(5) Uani 1 1 d . . . . .
C4' C 0.60593(15) -0.15944(18) 0.37226(12) 0.0314(5) Uani 1 1 d . . . . .
H4' H 0.565537 -0.199474 0.339928 0.038 Uiso 1 1 calc R . . . .
C5' C 0.59910(14) -0.04072(18) 0.38092(12) 0.0290(5) Uani 1 1 d . . . . .
H5' H 0.553561 0.000644 0.354062 0.035 Uiso 1 1 calc R . . . .
C6' C 0.65761(13) 0.01932(17) 0.42818(11) 0.0222(4) Uani 1 1 d . . . . .
C7' C 0.64306(13) 0.14476(17) 0.44336(10) 0.0218(4) Uani 1 1 d . . . . .
C8' C 0.55652(14) 0.18171(18) 0.46042(11) 0.0277(5) Uani 1 1 d . . . . .
H8' H 0.507563 0.128246 0.457718 0.033 Uiso 1 1 calc R . . . .
C9' C 0.54065(14) 0.29456(19) 0.48115(12) 0.0310(5) Uani 1 1 d . . . . .
H9' H 0.481483 0.317637 0.493480 0.037 Uiso 1 1 calc R . . . .
C10' C 0.61096(14) 0.37392(18) 0.48394(11) 0.0287(5) Uani 1 1 d . . . . .
H10' H 0.600266 0.451363 0.498574 0.034 Uiso 1 1 calc R . . . .
C11' C 0.69687(14) 0.34022(17) 0.46538(11) 0.0254(5) Uani 1 1 d . . . . .
H11' H 0.744878 0.395082 0.466137 0.031 Uiso 1 1 calc R . . . .
C12' C 0.71309(13) 0.22609(16) 0.44559(10) 0.0211(4) Uani 1 1 d . . . . .
C13' C 0.87494(13) 0.20222(17) 0.47152(11) 0.0226(5) Uani 1 1 d . . . . .
C14' C 0.96195(13) 0.16518(17) 0.43944(10) 0.0218(4) Uani 1 1 d . . . . .
C15' C 1.03678(14) 0.23751(17) 0.43593(12) 0.0284(5) Uani 1 1 d . . . . .
C16' C 1.12046(15) 0.1027(2) 0.38040(12) 0.0361(6) Uani 1 1 d . . . . .
H16' H 1.174905 0.081212 0.358380 0.043 Uiso 1 1 calc R . . . .
C17' C 1.05305(16) 0.0219(2) 0.38398(12) 0.0355(6) Uani 1 1 d . . . . .
H17' H 1.061872 -0.054846 0.367350 0.043 Uiso 1 1 calc R . . . .
C18' C 0.97193(15) 0.05439(18) 0.41228(11) 0.0297(5) Uani 1 1 d . . . . .
H18' H 0.923051 0.000939 0.413137 0.036 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 C3 1.7497(19) . ?
Cl2 C15 1.744(2) . ?
Cl1' C3' 1.747(2) . ?
Cl2' C15' 1.735(2) . ?
O1 C13 1.228(2) . ?
O1' C13' 1.230(2) . ?
N1 H19 0.883(9) . ?
N1 C12 1.437(2) . ?
N1 C13 1.336(2) . ?
N2 C15 1.322(2) . ?
N2 C16 1.338(3) . ?
N1' H19' 0.889(9) . ?
N1' C12' 1.429(2) . ?
N1' C13' 1.338(2) . ?
N2' C15' 1.321(3) . ?
N2' C16' 1.343(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(3) . ?
C1 C6 1.391(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.367(3) . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(3) . ?
C6 C7 1.491(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.398(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(3) . ?
C13 C14 1.507(3) . ?
C14 C15 1.392(3) . ?
C14 C18 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.375(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C1' H1' 0.9500 . ?
C1' C2' 1.387(3) . ?
C1' C6' 1.396(3) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.377(3) . ?
C3' C4' 1.374(3) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.385(3) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.392(3) . ?
C6' C7' 1.493(3) . ?
C7' C8' 1.395(3) . ?
C7' C12' 1.396(3) . ?
C8' H8' 0.9500 . ?
C8' C9' 1.382(3) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.384(3) . ?
C10' H10' 0.9500 . ?
C10' C11' 1.384(3) . ?
C11' H11' 0.9500 . ?
C11' C12' 1.392(3) . ?
C13' C14' 1.501(3) . ?
C14' C15' 1.388(3) . ?
C14' C18' 1.386(3) . ?
C16' H16' 0.9500 . ?
C16' C17' 1.367(3) . ?
C17' H17' 0.9500 . ?
C17' C18' 1.379(3) . ?
C18' H18' 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
C12 N1 H19 118.5(13) . . ?
C13 N1 H19 121.7(13) . . ?
C13 N1 C12 119.68(16) . . ?
C15 N2 C16 116.79(17) . . ?
C12' N1' H19' 117.8(13) . . ?
C13' N1' H19' 119.1(13) . . ?
C13' N1' C12' 123.04(16) . . ?
C15' N2' C16' 116.35(19) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.00(19) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.27(19) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 Cl1 118.03(15) . . ?
C2 C3 C4 121.47(18) . . ?
C4 C3 Cl1 120.50(16) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.73(18) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.01(18) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 118.11(17) . . ?
C5 C6 C1 118.49(17) . . ?
C5 C6 C7 123.39(17) . . ?
C8 C7 C6 121.55(17) . . ?
C8 C7 C12 117.68(17) . . ?
C12 C7 C6 120.59(16) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.73(18) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.34(19) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.95(18) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.72(18) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 N1 119.36(16) . . ?
C11 C12 N1 119.14(17) . . ?
C11 C12 C7 121.44(17) . . ?
O1 C13 N1 123.47(17) . . ?
O1 C13 C14 121.87(18) . . ?
N1 C13 C14 114.62(17) . . ?
C15 C14 C13 123.16(17) . . ?
C18 C14 C13 120.25(17) . . ?
C18 C14 C15 116.57(17) . . ?
N2 C15 Cl2 115.52(15) . . ?
N2 C15 C14 125.09(18) . . ?
C14 C15 Cl2 119.30(15) . . ?
N2 C16 H16 118.3 . . ?
N2 C16 C17 123.41(19) . . ?
C17 C16 H16 118.3 . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.52(19) . . ?
C18 C17 H17 120.7 . . ?
C14 C18 C17 119.61(19) . . ?
C14 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C2' C1' H1' 119.5 . . ?
C2' C1' C6' 120.93(19) . . ?
C6' C1' H1' 119.5 . . ?
C1' C2' H2' 120.5 . . ?
C3' C2' C1' 119.0(2) . . ?
C3' C2' H2' 120.5 . . ?
C2' C3' Cl1' 117.91(17) . . ?
C4' C3' Cl1' 120.32(16) . . ?
C4' C3' C2' 121.75(19) . . ?
C3' C4' H4' 120.6 . . ?
C3' C4' C5' 118.8(2) . . ?
C5' C4' H4' 120.6 . . ?
C4' C5' H5' 119.3 . . ?
C4' C5' C6' 121.4(2) . . ?
C6' C5' H5' 119.3 . . ?
C1' C6' C7' 120.77(18) . . ?
C5' C6' C1' 118.16(19) . . ?
C5' C6' C7' 120.84(18) . . ?
C8' C7' C6' 118.68(17) . . ?
C8' C7' C12' 118.09(18) . . ?
C12' C7' C6' 123.12(17) . . ?
C7' C8' H8' 119.4 . . ?
C9' C8' C7' 121.3(2) . . ?
C9' C8' H8' 119.4 . . ?
C8' C9' H9' 120.0 . . ?
C8' C9' C10' 119.97(19) . . ?
C10' C9' H9' 120.0 . . ?
C9' C10' H10' 120.1 . . ?
C11' C10' C9' 119.85(19) . . ?
C11' C10' H10' 120.1 . . ?
C10' C11' H11' 119.9 . . ?
C10' C11' C12' 120.12(19) . . ?
C12' C11' H11' 119.9 . . ?
C7' C12' N1' 120.40(17) . . ?
C11' C12' N1' 118.94(17) . . ?
C11' C12' C7' 120.65(18) . . ?
O1' C13' N1' 124.36(18) . . ?
O1' C13' C14' 121.72(18) . . ?
N1' C13' C14' 113.85(17) . . ?
C15' C14' C13' 122.86(17) . . ?
C18' C14' C13' 120.94(18) . . ?
C18' C14' C15' 116.19(18) . . ?
N2' C15' Cl2' 114.58(16) . . ?
N2' C15' C14' 125.40(19) . . ?
C14' C15' Cl2' 120.01(15) . . ?
N2' C16' H16' 118.2 . . ?
N2' C16' C17' 123.5(2) . . ?
C17' C16' H16' 118.2 . . ?
C16' C17' H17' 120.7 . . ?
C16' C17' C18' 118.5(2) . . ?
C18' C17' H17' 120.7 . . ?
C14' C18' H18' 120.1 . . ?
C17' C18' C14' 119.8(2) . . ?
C17' C18' H18' 120.1 . . ?

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
N1 H19 O1' 0.883(9) 2.007(11) 2.871(2) 165.9(18) 4_565
N1' H19' O1 0.889(9) 1.923(10) 2.808(2) 173.7(19) .

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 C3 C4 C5 178.56(15) . . . . ?
Cl1' C3' C4' C5' 177.15(16) . . . . ?
O1 C13 C14 C15 -57.3(3) . . . . ?
O1 C13 C14 C18 121.2(2) . . . . ?
O1' C13' C14' C15' -60.4(3) . . . . ?
O1' C13' C14' C18' 118.7(2) . . . . ?
N1 C13 C14 C15 125.0(2) . . . . ?
N1 C13 C14 C18 -56.5(2) . . . . ?
N2 C16 C17 C18 -0.6(3) . . . . ?
N1' C13' C14' C15' 122.4(2) . . . . ?
N1' C13' C14' C18' -58.5(2) . . . . ?
N2' C16' C17' C18' 3.5(3) . . . . ?
C1 C2 C3 Cl1 179.88(15) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C6 C7 C8 -114.4(2) . . . . ?
C1 C6 C7 C12 60.7(3) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
C2 C1 C6 C7 177.25(18) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 C7 -178.80(17) . . . . ?
C5 C6 C7 C8 64.7(3) . . . . ?
C5 C6 C7 C12 -120.2(2) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
C6 C7 C8 C9 172.7(2) . . . . ?
C6 C7 C12 N1 11.7(3) . . . . ?
C6 C7 C12 C11 -171.29(18) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C7 C12 N1 -173.00(17) . . . . ?
C8 C7 C12 C11 4.0(3) . . . . ?
C8 C9 C10 C11 2.9(3) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 N1 174.95(18) . . . . ?
C10 C11 C12 C7 -2.1(3) . . . . ?
C12 N1 C13 O1 -1.8(3) . . . . ?
C12 N1 C13 C14 175.78(15) . . . . ?
C12 C7 C8 C9 -2.6(3) . . . . ?
C13 N1 C12 C7 70.7(2) . . . . ?
C13 N1 C12 C11 -106.4(2) . . . . ?
C13 C14 C15 Cl2 -5.8(3) . . . . ?
C13 C14 C15 N2 177.96(19) . . . . ?
C13 C14 C18 C17 -178.06(19) . . . . ?
C15 N2 C16 C17 0.5(3) . . . . ?
C15 C14 C18 C17 0.5(3) . . . . ?
C16 N2 C15 Cl2 -176.30(15) . . . . ?
C16 N2 C15 C14 0.1(3) . . . . ?
C16 C17 C18 C14 0.0(3) . . . . ?
C18 C14 C15 Cl2 175.65(15) . . . . ?
C18 C14 C15 N2 -0.6(3) . . . . ?
C1' C2' C3' Cl1' -177.51(15) . . . . ?
C1' C2' C3' C4' 0.8(3) . . . . ?
C1' C6' C7' C8' -125.9(2) . . . . ?
C1' C6' C7' C12' 50.1(3) . . . . ?
C2' C1' C6' C5' -1.9(3) . . . . ?
C2' C1' C6' C7' 172.62(18) . . . . ?
C2' C3' C4' C5' -1.1(3) . . . . ?
C3' C4' C5' C6' -0.1(3) . . . . ?
C4' C5' C6' C1' 1.6(3) . . . . ?
C4' C5' C6' C7' -172.94(19) . . . . ?
C5' C6' C7' C8' 48.5(3) . . . . ?
C5' C6' C7' C12' -135.5(2) . . . . ?
C6' C1' C2' C3' 0.8(3) . . . . ?
C6' C7' C8' C9' 174.22(19) . . . . ?
C6' C7' C12' N1' 6.0(3) . . . . ?
C6' C7' C12' C11' -175.07(19) . . . . ?
C7' C8' C9' C10' 1.3(3) . . . . ?
C8' C7' C12' N1' -177.93(18) . . . . ?
C8' C7' C12' C11' 1.0(3) . . . . ?
C8' C9' C10' C11' 0.5(3) . . . . ?
C9' C10' C11' C12' -1.5(3) . . . . ?
C10' C11' C12' N1' 179.70(18) . . . . ?
C10' C11' C12' C7' 0.8(3) . . . . ?
C12' N1' C13' O1' 3.9(3) . . . . ?
C12' N1' C13' C14' -179.09(16) . . . . ?
C12' C7' C8' C9' -2.0(3) . . . . ?
C13' N1' C12' C7' -120.2(2) . . . . ?
C13' N1' C12' C11' 60.8(3) . . . . ?
C13' C14' C15' Cl2' 1.2(3) . . . . ?
C13' C14' C15' N2' -177.7(2) . . . . ?
C13' C14' C18' C17' -179.09(19) . . . . ?
C15' N2' C16' C17' -0.6(3) . . . . ?
C15' C14' C18' C17' 0.1(3) . . . . ?
C16' N2' C15' Cl2' 178.17(16) . . . . ?
C16' N2' C15' C14' -2.9(3) . . . . ?
C16' C17' C18' C14' -3.1(3) . . . . ?
C18' C14' C15' Cl2' -177.97(16) . . . . ?
C18' C14' C15' N2' 3.1(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_b
_database_code_depnum_ccdc_archive 'CCDC 1900704'
loop_
_audit_author_name
_audit_author_address
'Zhonghua Li'
;Tianjin University
China
;
_audit_update_record             
;
2019-03-03 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2017-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 Cl2 N2 O'
_chemical_formula_sum            'C18 H12 Cl2 N2 O'
_chemical_formula_weight         343.20
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.586(2)
_cell_length_b                   11.339(2)
_cell_length_c                   12.896(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.59(3)
_cell_angle_gamma                90.00
_cell_volume                     1540.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13908
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.75
_cell_measurement_theta_min      3.08
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.9388
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Pyramid
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15977
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.20
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2823
_reflns_number_total             3535
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1513
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C11(H11A), C5(H5A), C1(H1A), C18(H18A), C16(H16A), C2(H2A), C8(H8A),
 C17(H17A), C10(H10A), C9(H9A), N1(H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.20447(15) 1.04373(17) 0.24624(18) 0.0675(6) Uani 1 d . . .
Cl1 Cl 0.35108(6) 0.84787(6) -0.17366(5) 0.0561(2) Uani 1 d . . .
Cl2 Cl 0.37894(6) 0.88125(5) 0.17111(5) 0.0499(2) Uani 1 d . . .
C14 C 0.42614(17) 1.06448(17) 0.31680(16) 0.0299(4) Uani 1 d . . .
C15 C 0.47186(19) 0.95979(17) 0.29189(17) 0.0326(4) Uani 1 d . . .
C7 C 0.09897(17) 1.20292(18) 0.00497(16) 0.0304(4) Uani 1 d . . .
C3 C 0.2772(2) 0.95175(18) -0.12298(17) 0.0366(5) Uani 1 d . . .
C4 C 0.33966(19) 1.05398(18) -0.07543(17) 0.0350(5) Uani 1 d . . .
H4A H 0.4199 1.0688 -0.0726 0.042 Uiso 1 calc . . R
C11 C 0.0939(2) 1.32889(19) 0.15352(19) 0.0398(5) Uani 1 d . . .
H11A H 0.1321 1.3564 0.2282 0.048 Uiso 1 calc . . R
C5 C 0.28298(18) 1.13436(17) -0.03193(17) 0.0321(4) Uani 1 d . . .
H5A H 0.3263 1.2028 0.0025 0.039 Uiso 1 calc . . R
C1 C 0.0997(2) 1.0124(2) -0.09073(18) 0.0385(5) Uani 1 d . . .
H1A H 0.0177 0.9989 -0.0974 0.046 Uiso 1 calc . . R
C18 C 0.50801(19) 1.12585(18) 0.41068(18) 0.0343(5) Uani 1 d . . .
H18A H 0.4832 1.1977 0.4297 0.041 Uiso 1 calc . . R
C13 C 0.29165(18) 1.10315(19) 0.24861(18) 0.0339(5) Uani 1 d . . .
C12 C 0.15510(17) 1.24671(16) 0.11581(16) 0.0295(4) Uani 1 d . . .
C6 C 0.16248(18) 1.11492(17) -0.03860(16) 0.0297(4) Uani 1 d . . .
C16 C 0.6596(2) 0.97513(19) 0.44518(19) 0.0399(5) Uani 1 d . . .
H16A H 0.7387 0.9436 0.4906 0.048 Uiso 1 calc . . R
C2 C 0.1568(2) 0.9307(2) -0.13262(18) 0.0415(5) Uani 1 d . . .
H2A H 0.1142 0.8620 -0.1671 0.050 Uiso 1 calc . . R
C8 C -0.0209(2) 1.2446(2) -0.06587(18) 0.0442(6) Uani 1 d . . .
H8A H -0.0612 1.2159 -0.1399 0.053 Uiso 1 calc . . R
C17 C 0.62683(19) 1.0810(2) 0.47656(19) 0.0381(5) Uani 1 d . . .
H17A H 0.6830 1.1214 0.5403 0.046 Uiso 1 calc . . R
C10 C -0.0235(2) 1.3703(2) 0.0809(2) 0.0481(6) Uani 1 d . . .
H10A H -0.0640 1.4272 0.1057 0.058 Uiso 1 calc . . R
C9 C -0.0808(2) 1.3275(2) -0.0282(2) 0.0515(6) Uani 1 d . . .
H9A H -0.1608 1.3549 -0.0770 0.062 Uiso 1 calc . . R
N1 N 0.27746(14) 1.20459(14) 0.19298(13) 0.0292(4) Uani 1 d . . .
H1B H 0.3435 1.2461 0.2036 0.035 Uiso 1 calc . . R
N2 N 0.58389(16) 0.91456(15) 0.35271(16) 0.0383(4) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.204(2) . ?
Cl1 C3 1.736(2) . ?
Cl2 C15 1.727(2) . ?
C14 C15 1.391(3) . ?
C14 C18 1.376(3) . ?
C14 C13 1.501(3) . ?
C15 N2 1.310(3) . ?
C7 C12 1.392(3) . ?
C7 C6 1.482(3) . ?
C7 C8 1.390(3) . ?
C3 C4 1.369(3) . ?
C3 C2 1.369(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.372(3) . ?
C11 H11A 0.9300 . ?
C11 C12 1.376(3) . ?
C11 C10 1.374(3) . ?
C5 H5A 0.9300 . ?
C5 C6 1.380(3) . ?
C1 H1A 0.9300 . ?
C1 C6 1.387(3) . ?
C1 C2 1.373(3) . ?
C18 H18A 0.9300 . ?
C18 C17 1.379(3) . ?
C13 N1 1.329(3) . ?
C12 N1 1.433(2) . ?
C16 H16A 0.9300 . ?
C16 C17 1.370(3) . ?
C16 N2 1.339(3) . ?
C2 H2A 0.9300 . ?
C8 H8A 0.9300 . ?
C8 C9 1.372(3) . ?
C17 H17A 0.9300 . ?
C10 H10A 0.9300 . ?
C10 C9 1.370(3) . ?
C9 H9A 0.9300 . ?
N1 H1B 0.8600 . ?

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
C15 C14 C13 121.08(18) . . ?
C18 C14 C15 116.45(18) . . ?
C18 C14 C13 122.35(19) . . ?
C14 C15 Cl2 119.61(16) . . ?
N2 C15 Cl2 115.38(16) . . ?
N2 C15 C14 125.00(19) . . ?
C12 C7 C6 122.39(17) . . ?
C12 C7 C8 117.74(19) . . ?
C8 C7 C6 119.87(18) . . ?
C4 C3 Cl1 119.43(17) . . ?
C2 C3 Cl1 119.42(17) . . ?
C2 C3 C4 121.1(2) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4A 120.3 . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 C12 120.0(2) . . ?
C4 C5 H5A 119.6 . . ?
C4 C5 C6 120.81(19) . . ?
C6 C5 H5A 119.6 . . ?
C6 C1 H1A 119.5 . . ?
C2 C1 H1A 119.5 . . ?
C2 C1 C6 120.97(19) . . ?
C14 C18 H18A 120.0 . . ?
C14 C18 C17 120.1(2) . . ?
C17 C18 H18A 120.0 . . ?
O1 C13 C14 120.45(19) . . ?
O1 C13 N1 123.82(19) . . ?
N1 C13 C14 115.73(16) . . ?
C7 C12 N1 119.90(17) . . ?
C11 C12 C7 120.99(18) . . ?
C11 C12 N1 119.10(18) . . ?
C5 C6 C7 121.17(18) . . ?
C5 C6 C1 118.48(19) . . ?
C1 C6 C7 120.31(18) . . ?
C17 C16 H16A 118.2 . . ?
N2 C16 H16A 118.2 . . ?
N2 C16 C17 123.60(19) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2A 120.5 . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 H8A 119.5 . . ?
C18 C17 C16 118.0(2) . . ?
C18 C17 H17A 121.0 . . ?
C16 C17 H17A 121.0 . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H10A 120.0 . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C13 N1 C12 121.85(16) . . ?
C13 N1 H1B 119.1 . . ?
C12 N1 H1B 119.1 . . ?
C15 N2 C16 116.81(18) . . ?

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
O1 C13 N1 C12 -6.1(3) . . . . ?
Cl1 C3 C4 C5 -177.85(15) . . . . ?
Cl1 C3 C2 C1 178.99(17) . . . . ?
Cl2 C15 N2 C16 178.19(15) . . . . ?
C14 C15 N2 C16 -0.6(3) . . . . ?
C14 C18 C17 C16 0.2(3) . . . . ?
C14 C13 N1 C12 173.82(18) . . . . ?
C15 C14 C18 C17 -2.0(3) . . . . ?
C15 C14 C13 O1 61.8(3) . . . . ?
C15 C14 C13 N1 -118.1(2) . . . . ?
C7 C12 N1 C13 -80.8(3) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C3 C4 C5 C6 -1.9(3) . . . . ?
C4 C3 C2 C1 -1.9(3) . . . . ?
C4 C5 C6 C7 -178.11(18) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C11 C12 N1 C13 98.1(2) . . . . ?
C11 C10 C9 C8 -0.8(4) . . . . ?
C18 C14 C15 Cl2 -176.37(15) . . . . ?
C18 C14 C15 N2 2.3(3) . . . . ?
C18 C14 C13 O1 -114.2(3) . . . . ?
C18 C14 C13 N1 66.0(3) . . . . ?
C13 C14 C15 Cl2 7.5(3) . . . . ?
C13 C14 C15 N2 -173.84(19) . . . . ?
C13 C14 C18 C17 174.08(18) . . . . ?
C12 C7 C6 C5 -53.8(3) . . . . ?
C12 C7 C6 C1 128.4(2) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C12 C11 C10 C9 1.5(4) . . . . ?
C6 C7 C12 C11 179.64(19) . . . . ?
C6 C7 C12 N1 -1.4(3) . . . . ?
C6 C7 C8 C9 -178.9(2) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C2 C3 C4 C5 3.0(3) . . . . ?
C2 C1 C6 C7 179.28(19) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C8 C7 C12 N1 178.63(18) . . . . ?
C8 C7 C6 C5 126.1(2) . . . . ?
C8 C7 C6 C1 -51.7(3) . . . . ?
C17 C16 N2 C15 -1.6(3) . . . . ?
C10 C11 C12 C7 -1.0(3) . . . . ?
C10 C11 C12 N1 -179.9(2) . . . . ?
N2 C16 C17 C18 1.8(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_b_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1900705'
loop_
_audit_author_name
_audit_author_address
'Zhonghua Li'
;Tianjin University
China
;
_audit_update_record             
;
2019-03-03 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2017-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 Cl2 N2 O, H2 O'
_chemical_formula_sum            'C18 H14 Cl2 N2 O2'
_chemical_formula_weight         361.21
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.9355(14)
_cell_length_b                   9.4200(19)
_cell_length_c                   13.620(3)
_cell_angle_alpha                104.22(3)
_cell_angle_beta                 98.12(3)
_cell_angle_gamma                93.71(3)
_cell_volume                     849.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3453
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      3.04
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  0.9432
_exptl_absorpt_correction_T_min  0.9078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.2560
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6944
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         3.05
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1856
_reflns_number_total             3109
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.11(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3109
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0949
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1576P)²+0.3010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2673
_refine_ls_wR_factor_ref         0.2957
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
3.a Aromatic/amide H refined with riding coordinates:
 N1(H19), C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C18(H18), C17(H17), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.3263(3) 0.50707(18) 0.65776(12) 0.0810(7) Uani 1 1 d . . .
Cl1 Cl -0.3695(3) 0.6212(2) 0.91024(13) 0.0870(7) Uani 1 1 d . . .
N1 N 0.1877(6) 0.1466(5) 0.6547(3) 0.0474(11) Uani 1 1 d . . .
H19 H 0.0753 0.1760 0.6392 0.057 Uiso 1 1 calc R . .
N2 N 0.2227(8) 0.4640(6) 0.4606(4) 0.0664(14) Uani 1 1 d . . .
O1 O 0.4947(6) 0.1391(5) 0.6180(4) 0.0722(13) Uani 1 1 d . . .
OW1 O -0.1642(7) 0.2351(6) 0.5628(4) 0.0773(14) Uani 1 1 d D . .
C1 C 0.0734(8) 0.3865(6) 0.8463(4) 0.0526(13) Uani 1 1 d . . .
H1 H 0.2024 0.4049 0.8374 0.063 Uiso 1 1 calc R . .
C2 C -0.0361(10) 0.5019(6) 0.8688(4) 0.0598(15) Uani 1 1 d . . .
H2 H 0.0189 0.5975 0.8764 0.072 Uiso 1 1 calc R . .
C3 C -0.2296(10) 0.4763(7) 0.8804(4) 0.0607(15) Uani 1 1 d . . .
C4 C -0.3084(9) 0.3323(8) 0.8701(5) 0.0705(17) Uani 1 1 d . . .
H4 H -0.4371 0.3141 0.8794 0.085 Uiso 1 1 calc R . .
C5 C -0.1982(9) 0.2192(7) 0.8467(5) 0.0618(15) Uani 1 1 d . . .
H5 H -0.2540 0.1233 0.8373 0.074 Uiso 1 1 calc R . .
C6 C -0.0010(8) 0.2438(6) 0.8362(4) 0.0484(13) Uani 1 1 d . . .
C7 C 0.1202(8) 0.1193(6) 0.8203(4) 0.0491(13) Uani 1 1 d . . .
C8 C 0.1496(9) 0.0426(6) 0.8971(4) 0.0601(15) Uani 1 1 d . . .
H8 H 0.0904 0.0713 0.9550 0.072 Uiso 1 1 calc R . .
C9 C 0.2622(11) -0.0725(7) 0.8893(5) 0.0689(17) Uani 1 1 d . . .
H9 H 0.2782 -0.1213 0.9411 0.083 Uiso 1 1 calc R . .
C10 C 0.3511(10) -0.1151(6) 0.8046(5) 0.0674(17) Uani 1 1 d . . .
H10 H 0.4308 -0.1914 0.7997 0.081 Uiso 1 1 calc R . .
C11 C 0.3225(8) -0.0445(6) 0.7260(4) 0.0556(14) Uani 1 1 d . . .
H11 H 0.3777 -0.0773 0.6671 0.067 Uiso 1 1 calc R . .
C12 C 0.2137(7) 0.0732(5) 0.7346(4) 0.0462(12) Uani 1 1 d . . .
C13 C 0.3314(7) 0.1720(6) 0.6024(4) 0.0459(12) Uani 1 1 d . . .
C14 C 0.2692(7) 0.2468(6) 0.5177(4) 0.0428(12) Uani 1 1 d . . .
C18 C 0.2278(9) 0.1611(7) 0.4167(4) 0.0581(14) Uani 1 1 d . . .
H18 H 0.2326 0.0598 0.4017 0.070 Uiso 1 1 calc R . .
C17 C 0.1791(11) 0.2308(8) 0.3387(4) 0.0736(19) Uani 1 1 d . . .
H17 H 0.1458 0.1766 0.2707 0.088 Uiso 1 1 calc R . .
C16 C 0.1812(10) 0.3786(8) 0.3642(5) 0.0694(18) Uani 1 1 d . . .
H16 H 0.1520 0.4244 0.3115 0.083 Uiso 1 1 calc R . .
C15 C 0.2666(8) 0.3953(6) 0.5331(4) 0.0537(14) Uani 1 1 d . . .
HW1A H -0.273(9) 0.209(7) 0.584(5) 0.074(19) Uiso 1 1 d D . .
HW1B H -0.153(18) 0.342(10) 0.550(9) 0.18(4) Uiso 1 1 d D . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C15 1.741(6) . ?
Cl1 C3 1.727(7) . ?
N1 H19 0.8600 . ?
N1 C12 1.423(6) . ?
N1 C13 1.347(6) . ?
N2 C16 1.341(9) . ?
N2 C15 1.318(7) . ?
O1 C13 1.197(6) . ?
OW1 HW1A 0.88(6) . ?
OW1 HW1B 1.06(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.365(8) . ?
C1 C6 1.376(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(9) . ?
C3 C4 1.396(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.352(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.406(8) . ?
C6 C7 1.478(8) . ?
C7 C8 1.409(7) . ?
C7 C12 1.404(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.369(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(7) . ?
C13 C14 1.520(7) . ?
C14 C18 1.392(8) . ?
C14 C15 1.365(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.394(8) . ?
C17 H17 0.9300 . ?
C17 C16 1.349(10) . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 H19 118.6 . . ?
C13 N1 H19 118.6 . . ?
C13 N1 C12 122.9(4) . . ?
C15 N2 C16 116.1(5) . . ?
HW1A OW1 HW1B 116(8) . . ?
C2 C1 H1 119.0 . . ?
C2 C1 C6 122.0(6) . . ?
C6 C1 H1 119.0 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 Cl1 120.4(5) . . ?
C2 C3 C4 119.2(6) . . ?
C4 C3 Cl1 120.4(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(6) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(6) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.6(5) . . ?
C1 C6 C7 122.6(5) . . ?
C5 C6 C7 119.7(5) . . ?
C8 C7 C6 118.4(5) . . ?
C12 C7 C6 124.6(4) . . ?
C12 C7 C8 116.9(5) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.3(6) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(5) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(6) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.5(6) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 N1 119.1(5) . . ?
C11 C12 N1 120.3(5) . . ?
C11 C12 C7 120.6(5) . . ?
N1 C13 C14 114.0(4) . . ?
O1 C13 N1 124.9(5) . . ?
O1 C13 C14 121.1(4) . . ?
C18 C14 C13 118.5(5) . . ?
C15 C14 C13 124.0(5) . . ?
C15 C14 C18 117.2(5) . . ?
C14 C18 H18 120.8 . . ?
C14 C18 C17 118.5(6) . . ?
C17 C18 H18 120.8 . . ?
C18 C17 H17 120.8 . . ?
C16 C17 C18 118.4(6) . . ?
C16 C17 H17 120.8 . . ?
N2 C16 C17 124.3(5) . . ?
N2 C16 H16 117.9 . . ?
C17 C16 H16 117.9 . . ?
N2 C15 Cl2 115.9(4) . . ?
N2 C15 C14 125.5(5) . . ?
C14 C15 Cl2 118.7(4) . . ?

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 C3 C4 C5 180.0(5) . . . . ?
N1 C13 C14 C18 -101.4(6) . . . . ?
N1 C13 C14 C15 84.2(6) . . . . ?
O1 C13 C14 C18 78.0(7) . . . . ?
O1 C13 C14 C15 -96.4(7) . . . . ?
C1 C2 C3 Cl1 179.3(4) . . . . ?
C1 C2 C3 C4 0.9(8) . . . . ?
C1 C6 C7 C8 115.5(6) . . . . ?
C1 C6 C7 C12 -62.8(7) . . . . ?
C2 C1 C6 C5 2.0(8) . . . . ?
C2 C1 C6 C7 -174.8(5) . . . . ?
C2 C3 C4 C5 -1.6(9) . . . . ?
C3 C4 C5 C6 2.6(9) . . . . ?
C4 C5 C6 C1 -2.7(8) . . . . ?
C4 C5 C6 C7 174.2(5) . . . . ?
C5 C6 C7 C8 -61.2(7) . . . . ?
C5 C6 C7 C12 120.5(6) . . . . ?
C6 C1 C2 C3 -1.2(8) . . . . ?
C6 C7 C8 C9 -179.0(5) . . . . ?
C6 C7 C12 N1 -2.0(7) . . . . ?
C6 C7 C12 C11 -179.6(5) . . . . ?
C7 C8 C9 C10 0.4(10) . . . . ?
C8 C7 C12 N1 179.7(5) . . . . ?
C8 C7 C12 C11 2.1(7) . . . . ?
C8 C9 C10 C11 -1.8(10) . . . . ?
C9 C10 C11 C12 3.4(9) . . . . ?
C10 C11 C12 N1 178.9(5) . . . . ?
C10 C11 C12 C7 -3.5(8) . . . . ?
C12 N1 C13 O1 -1.6(9) . . . . ?
C12 N1 C13 C14 177.8(4) . . . . ?
C12 C7 C8 C9 -0.5(8) . . . . ?
C13 N1 C12 C7 143.5(5) . . . . ?
C13 N1 C12 C11 -38.9(7) . . . . ?
C13 C14 C18 C17 -177.3(5) . . . . ?
C13 C14 C15 Cl2 -3.2(7) . . . . ?
C13 C14 C15 N2 176.5(5) . . . . ?
C14 C18 C17 C16 2.4(10) . . . . ?
C18 C14 C15 Cl2 -177.7(4) . . . . ?
C18 C14 C15 N2 2.0(8) . . . . ?
C18 C17 C16 N2 -1.7(11) . . . . ?
C16 N2 C15 Cl2 178.5(5) . . . . ?
C16 N2 C15 C14 -1.3(9) . . . . ?
C15 N2 C16 C17 1.1(10) . . . . ?
C15 C14 C18 C17 -2.5(8) . . . . ?

_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_b_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1900707'
loop_
_audit_author_name
_audit_author_address
'Zhonghua Li'
;Tianjin University
China
;
_audit_update_record             
;
2019-03-03 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2019-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 Cl2 N2 O, C5 H9 N O'
_chemical_formula_sum            'C23 H21 Cl2 N3 O2'
_chemical_formula_weight         442.33
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   9.7298(19)
_cell_length_b                   10.184(2)
_cell_length_c                   12.954(3)
_cell_angle_alpha                107.11(3)
_cell_angle_beta                 104.35(3)
_cell_angle_gamma                106.29(3)
_cell_volume                     1098.5(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4069
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      3.08
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  0.9536
_exptl_absorpt_correction_T_min  0.9243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Pyramid
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9149
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         3.084
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3093
_reflns_number_total             4069
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.586
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.070(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0808
_refine_ls_restrained_S_all      1.106
_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)+(0.1544P)²+0.6369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2479
_refine_ls_wR_factor_ref         0.2656
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C3AA(H3AA,H3AB), C4AA(H4AA,H4AB)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C15(H15), C3(H3), C10(H10), C14(H14), C9(H9), C11(H11),
 C1(H1), C17(H17), C2(H2A), C18(H18)
2.c Idealised Me refined as rotating group:
 C2AA(H2AA,H2AB,H2AC)
;
_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 0.88130(14) 0.14497(14) 0.40280(10) 0.0796(5) Uani 1 1 d . . . . .
Cl2 Cl 0.66284(16) 0.66117(16) 0.67415(12) 0.0968(5) Uani 1 1 d . . . . .
N2 N 0.7515(3) 0.4348(3) 0.8630(3) 0.0473(7) Uani 1 1 d . . . . .
H2 H 0.835750 0.434693 0.853232 0.057 Uiso 1 1 calc R . . . .
C12 C 0.6189(4) 0.1657(4) 0.7773(3) 0.0474(8) Uani 1 1 d . . . . .
C6 C 0.7235(4) 0.5602(4) 0.8767(3) 0.0493(8) Uani 1 1 d . . . . .
O1 O 0.6080(3) 0.5754(3) 0.8877(3) 0.0729(9) Uani 1 1 d . . . . .
C8 C 0.5929(4) 0.3109(4) 0.9509(3) 0.0526(8) Uani 1 1 d . . . . .
H8 H 0.614246 0.402922 1.007012 0.063 Uiso 1 1 calc R . . . .
C7 C 0.6517(4) 0.3029(4) 0.8635(3) 0.0451(7) Uani 1 1 d . . . . .
N1 N 0.9386(4) 0.8588(4) 0.7932(3) 0.0654(9) Uani 1 1 d . . . . .
C4 C 0.8512(4) 0.6853(4) 0.8773(3) 0.0479(8) Uani 1 1 d . . . . .
C15 C 0.8180(5) 0.0595(4) 0.5696(3) 0.0617(10) Uani 1 1 d . . . . .
H15 H 0.873230 -0.000416 0.554546 0.074 Uiso 1 1 calc R . . . .
C3 C 0.9918(4) 0.7504(4) 0.9662(3) 0.0565(9) Uani 1 1 d . . . . .
H3 H 1.010917 0.713956 1.023948 0.068 Uiso 1 1 calc R . . . .
C13 C 0.6759(4) 0.1551(4) 0.6809(3) 0.0484(8) Uani 1 1 d . . . . .
C10 C 0.4715(4) 0.0461(5) 0.8725(4) 0.0617(10) Uani 1 1 d . . . . .
H10 H 0.411909 -0.040945 0.875444 0.074 Uiso 1 1 calc R . . . .
C16 C 0.7953(4) 0.1429(4) 0.5057(3) 0.0580(9) Uani 1 1 d . . . . .
C14 C 0.7581(4) 0.0648(4) 0.6566(3) 0.0571(9) Uani 1 1 d . . . . .
H14 H 0.772854 0.007576 0.699405 0.068 Uiso 1 1 calc R . . . .
C9 C 0.5009(4) 0.1805(5) 0.9552(4) 0.0593(10) Uani 1 1 d . . . . .
H9 H 0.460486 0.185463 1.013525 0.071 Uiso 1 1 calc R . . . .
C5 C 0.8335(4) 0.7444(4) 0.7936(3) 0.0561(9) Uani 1 1 d . . . . .
C11 C 0.5294(4) 0.0382(4) 0.7846(3) 0.0566(9) Uani 1 1 d . . . . .
H11 H 0.508085 -0.054319 0.729224 0.068 Uiso 1 1 calc R . . . .
C1 C 1.0723(5) 0.9221(4) 0.8812(4) 0.0655(11) Uani 1 1 d . . . . .
H1 H 1.147266 1.004522 0.883947 0.079 Uiso 1 1 calc R . . . .
C17 C 0.7113(5) 0.2290(5) 0.5252(3) 0.0643(10) Uani 1 1 d . . . . .
H17 H 0.695325 0.284083 0.480816 0.077 Uiso 1 1 calc R . . . .
C2 C 1.1054(5) 0.8720(4) 0.9683(4) 0.0637(10) Uani 1 1 d . . . . .
H2A H 1.201300 0.918013 1.027284 0.076 Uiso 1 1 calc R . . . .
C18 C 0.6505(5) 0.2335(4) 0.6114(3) 0.0581(9) Uani 1 1 d . . . . .
H18 H 0.591401 0.290132 0.623066 0.070 Uiso 1 1 calc R . . . .
O0AA O 1.0271(3) 0.4176(3) 0.8399(3) 0.0685(8) Uani 1 1 d . . . . .
C0AA C 1.0994(5) 0.4272(6) 0.7767(4) 0.0816(14) Uani 1 1 d . . . . .
N0AA N 1.1844(5) 0.3665(6) 0.7476(4) 0.1075(16) Uani 1 1 d . . . . .
C1AA C 1.2555(6) 0.4008(7) 0.6695(5) 0.0883(15) Uani 1 1 d . . . . .
H1AA H 1.215600 0.316863 0.595989 0.106 Uiso 1 1 calc R . . . .
H1AB H 1.366138 0.432314 0.702287 0.106 Uiso 1 1 calc R . . . .
C2AA C 1.2005(7) 0.2584(6) 0.7909(5) 0.0898(15) Uani 1 1 d . . . . .
H2AA H 1.263844 0.306064 0.871564 0.135 Uiso 1 1 calc GR . . . .
H2AB H 1.247326 0.201532 0.749167 0.135 Uiso 1 1 calc GR . . . .
H2AC H 1.101199 0.193507 0.781692 0.135 Uiso 1 1 calc GR . . . .
C3AA C 1.1026(8) 0.5468(8) 0.7127(6) 0.1067(18) Uani 1 1 d . . . . .
H3AA H 1.002123 0.521449 0.657163 0.128 Uiso 1 1 calc R . . . .
H3AB H 1.138254 0.647735 0.768898 0.128 Uiso 1 1 calc R . . . .
C4AA C 1.2093(16) 0.5286(12) 0.6567(10) 0.194(5) Uani 1 1 d . . . . .
H4AA H 1.299775 0.619896 0.690766 0.232 Uiso 1 1 calc R . . . .
H4AB H 1.163073 0.507907 0.575261 0.232 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 C16 1.743(4) . ?
Cl2 C5 1.742(4) . ?
N2 H2 0.8600 . ?
N2 C6 1.350(4) . ?
N2 C7 1.423(4) . ?
C12 C7 1.399(5) . ?
C12 C13 1.475(5) . ?
C12 C11 1.390(5) . ?
C6 O1 1.213(4) . ?
C6 C4 1.506(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.382(5) . ?
C8 C9 1.403(5) . ?
N1 C5 1.320(5) . ?
N1 C1 1.331(6) . ?
C4 C3 1.378(5) . ?
C4 C5 1.385(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(6) . ?
C15 C14 1.385(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.398(5) . ?
C13 C14 1.397(5) . ?
C13 C18 1.390(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.367(6) . ?
C10 C11 1.382(6) . ?
C16 C17 1.368(6) . ?
C14 H14 0.9300 . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.373(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(5) . ?
C2 H2A 0.9300 . ?
C18 H18 0.9300 . ?
O0AA C0AA 1.211(5) . ?
C0AA N0AA 1.230(7) . ?
C0AA C3AA 1.661(9) . ?
N0AA C1AA 1.429(7) . ?
N0AA C2AA 1.403(8) . ?
C1AA H1AA 0.9700 . ?
C1AA H1AB 0.9700 . ?
C1AA C4AA 1.531(12) . ?
C2AA H2AA 0.9600 . ?
C2AA H2AB 0.9600 . ?
C2AA H2AC 0.9600 . ?
C3AA H3AA 0.9700 . ?
C3AA H3AB 0.9700 . ?
C3AA C4AA 1.428(13) . ?
C4AA H4AA 0.9700 . ?
C4AA H4AB 0.9700 . ?

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
C6 N2 H2 117.6 . . ?
C6 N2 C7 124.7(3) . . ?
C7 N2 H2 117.6 . . ?
C7 C12 C13 121.6(3) . . ?
C11 C12 C7 117.8(3) . . ?
C11 C12 C13 120.5(3) . . ?
N2 C6 C4 113.7(3) . . ?
O1 C6 N2 125.0(3) . . ?
O1 C6 C4 121.3(3) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C12 C7 N2 119.2(3) . . ?
C8 C7 N2 120.0(3) . . ?
C8 C7 C12 120.8(3) . . ?
C5 N1 C1 116.6(3) . . ?
C3 C4 C6 120.2(3) . . ?
C3 C4 C5 116.8(3) . . ?
C5 C4 C6 122.9(3) . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 119.0(4) . . ?
C2 C3 H3 120.5 . . ?
C14 C13 C12 120.5(3) . . ?
C18 C13 C12 121.8(3) . . ?
C18 C13 C14 117.7(3) . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C15 C16 Cl1 119.4(3) . . ?
C17 C16 Cl1 119.8(3) . . ?
C17 C16 C15 120.8(4) . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
N1 C5 Cl2 115.0(3) . . ?
N1 C5 C4 125.5(4) . . ?
C4 C5 Cl2 119.4(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.5(4) . . ?
C2 C1 H1 118.3 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 C3 118.5(4) . . ?
C1 C2 H2A 120.7 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
O0AA C0AA N0AA 133.5(6) . . ?
O0AA C0AA C3AA 121.3(5) . . ?
N0AA C0AA C3AA 105.2(5) . . ?
C0AA N0AA C1AA 120.9(6) . . ?
C0AA N0AA C2AA 116.1(6) . . ?
C2AA N0AA C1AA 122.9(5) . . ?
N0AA C1AA H1AA 111.5 . . ?
N0AA C1AA H1AB 111.5 . . ?
N0AA C1AA C4AA 101.2(5) . . ?
H1AA C1AA H1AB 109.4 . . ?
C4AA C1AA H1AA 111.5 . . ?
C4AA C1AA H1AB 111.5 . . ?
N0AA C2AA H2AA 109.5 . . ?
N0AA C2AA H2AB 109.5 . . ?
N0AA C2AA H2AC 109.5 . . ?
H2AA C2AA H2AB 109.5 . . ?
H2AA C2AA H2AC 109.5 . . ?
H2AB C2AA H2AC 109.5 . . ?
C0AA C3AA H3AA 111.4 . . ?
C0AA C3AA H3AB 111.4 . . ?
H3AA C3AA H3AB 109.3 . . ?
C4AA C3AA C0AA 101.9(6) . . ?
C4AA C3AA H3AA 111.4 . . ?
C4AA C3AA H3AB 111.4 . . ?
C1AA C4AA H4AA 109.6 . . ?
C1AA C4AA H4AB 109.6 . . ?
C3AA C4AA C1AA 110.3(6) . . ?
C3AA C4AA H4AA 109.6 . . ?
C3AA C4AA H4AB 109.6 . . ?
H4AA C4AA H4AB 108.1 . . ?

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 C16 C17 C18 -176.4(3) . . . . ?
N2 C6 C4 C3 -66.5(4) . . . . ?
N2 C6 C4 C5 116.1(4) . . . . ?
C12 C13 C14 C15 -177.0(3) . . . . ?
C12 C13 C18 C17 176.5(4) . . . . ?
C6 N2 C7 C12 133.5(3) . . . . ?
C6 N2 C7 C8 -48.8(5) . . . . ?
C6 C4 C3 C2 -176.2(3) . . . . ?
C6 C4 C5 Cl2 -6.3(5) . . . . ?
C6 C4 C5 N1 176.2(3) . . . . ?
O1 C6 C4 C3 113.5(4) . . . . ?
O1 C6 C4 C5 -63.9(5) . . . . ?
C7 N2 C6 O1 -2.3(6) . . . . ?
C7 N2 C6 C4 177.7(3) . . . . ?
C7 C12 C13 C14 126.7(4) . . . . ?
C7 C12 C13 C18 -53.3(5) . . . . ?
C7 C12 C11 C10 1.4(5) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
N1 C1 C2 C3 -1.6(6) . . . . ?
C4 C3 C2 C1 0.0(6) . . . . ?
C15 C16 C17 C18 0.9(6) . . . . ?
C3 C4 C5 Cl2 176.3(3) . . . . ?
C3 C4 C5 N1 -1.3(6) . . . . ?
C13 C12 C7 N2 -4.6(5) . . . . ?
C13 C12 C7 C8 177.8(3) . . . . ?
C13 C12 C11 C10 -178.2(3) . . . . ?
C16 C15 C14 C13 -0.5(6) . . . . ?
C16 C17 C18 C13 1.6(6) . . . . ?
C14 C15 C16 Cl1 175.9(3) . . . . ?
C14 C15 C16 C17 -1.5(6) . . . . ?
C14 C13 C18 C17 -3.4(6) . . . . ?
C9 C8 C7 N2 -176.7(3) . . . . ?
C9 C8 C7 C12 1.0(5) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C5 N1 C1 C2 1.7(6) . . . . ?
C5 C4 C3 C2 1.3(5) . . . . ?
C11 C12 C7 N2 175.7(3) . . . . ?
C11 C12 C7 C8 -1.9(5) . . . . ?
C11 C12 C13 C14 -53.6(5) . . . . ?
C11 C12 C13 C18 126.4(4) . . . . ?
C11 C10 C9 C8 -1.0(6) . . . . ?
C1 N1 C5 Cl2 -177.8(3) . . . . ?
C1 N1 C5 C4 -0.2(6) . . . . ?
C18 C13 C14 C15 2.9(5) . . . . ?
O0AA C0AA N0AA C1AA 179.9(5) . . . . ?
O0AA C0AA N0AA C2AA 2.8(9) . . . . ?
O0AA C0AA C3AA C4AA 175.4(6) . . . . ?
C0AA N0AA C1AA C4AA 6.2(8) . . . . ?
C0AA C3AA C4AA C1AA 6.1(10) . . . . ?
N0AA C0AA C3AA C4AA -2.5(8) . . . . ?
N0AA C1AA C4AA C3AA -7.4(10) . . . . ?
C2AA N0AA C1AA C4AA -176.8(7) . . . . ?
C3AA C0AA N0AA C1AA -2.6(7) . . . . ?
C3AA C0AA N0AA C2AA -179.7(5) . . . . ?

_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_b_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1900706'
loop_
_audit_author_name
_audit_author_address
'Zhonghua Li'
;Tianjin University
China
;
_audit_update_record             
;
2019-03-03 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2017-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 Cl2 N2 O, C2 H4 O'
_chemical_formula_sum            'C20 H16 Cl2 N2 O2'
_chemical_formula_weight         387.25
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.284(3)
_cell_length_b                   20.468(4)
_cell_length_c                   7.4983(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.21(3)
_cell_angle_gamma                90
_cell_volume                     1874.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7119
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      3.20
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.9476
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16514
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         3.202
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP'
_diffrn_measurement_method       'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2477
_reflns_number_total             4112
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0089(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.054
_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)+(0.0263P)²+1.2657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1243
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C1(H1), C5(H5), C8(H8), C2(H2), C10(H10), C18(H18), C4(H4), C9(H9),
 C17(H17), C16(H16), N1(H21)
;
_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
Cl2 Cl 0.24457(8) 0.09230(5) 0.08083(11) 0.0743(3) Uani 1 1 d . . . . .
Cl1 Cl 0.47795(8) -0.15275(5) 1.04839(11) 0.0793(3) Uani 1 1 d . . . . .
C6 C 0.2587(2) -0.14496(13) 0.5244(4) 0.0445(7) Uani 1 1 d . . . . .
C14 C 0.1578(2) 0.08493(13) 0.3966(4) 0.0443(7) Uani 1 1 d . . . . .
C7 C 0.1829(2) -0.14821(14) 0.3554(4) 0.0461(7) Uani 1 1 d . . . . .
C12 C 0.1340(2) -0.09295(14) 0.2695(4) 0.0426(7) Uani 1 1 d . . . . .
C13 C 0.0993(2) 0.02318(14) 0.3320(3) 0.0448(7) Uani 1 1 d . . . . .
C11 C 0.0608(2) -0.09982(16) 0.1162(4) 0.0548(8) Uani 1 1 d . . . . .
H11 H 0.030477 -0.062952 0.057667 0.066 Uiso 1 1 calc R . . . .
C1 C 0.2273(2) -0.11434(14) 0.6768(4) 0.0517(8) Uani 1 1 d . . . . .
H1 H 0.160895 -0.092203 0.670554 0.062 Uiso 1 1 calc R . . . .
C5 C 0.3587(2) -0.17756(14) 0.5383(4) 0.0511(7) Uani 1 1 d . . . . .
H5 H 0.380381 -0.198563 0.438014 0.061 Uiso 1 1 calc R . . . .
C8 C 0.1548(3) -0.20940(15) 0.2809(4) 0.0556(8) Uani 1 1 d . . . . .
H8 H 0.188382 -0.246589 0.332556 0.067 Uiso 1 1 calc R . . . .
C2 C 0.2943(3) -0.11669(15) 0.8375(4) 0.0557(8) Uani 1 1 d . . . . .
H2 H 0.272919 -0.096392 0.939008 0.067 Uiso 1 1 calc R . . . .
C10 C 0.0329(3) -0.16104(18) 0.0505(4) 0.0643(9) Uani 1 1 d . . . . .
H10 H -0.017465 -0.165367 -0.050666 0.077 Uiso 1 1 calc R . . . .
C18 C 0.1424(3) 0.11128(16) 0.5621(4) 0.0616(9) Uani 1 1 d . . . . .
H18 H 0.098571 0.089645 0.636783 0.074 Uiso 1 1 calc R . . . .
C3 C 0.3930(3) -0.14928(15) 0.8461(4) 0.0535(8) Uani 1 1 d . . . . .
C15 C 0.2243(3) 0.12068(15) 0.2943(4) 0.0530(8) Uani 1 1 d . . . . .
C4 C 0.4265(3) -0.17944(14) 0.6978(4) 0.0544(8) Uani 1 1 d . . . . .
H4 H 0.493686 -0.200754 0.704596 0.065 Uiso 1 1 calc R . . . .
C9 C 0.0790(3) -0.21593(18) 0.1336(4) 0.0633(9) Uani 1 1 d . . . . .
H9 H 0.058885 -0.257229 0.090010 0.076 Uiso 1 1 calc R . . . .
C17 C 0.1916(3) 0.16927(18) 0.6162(5) 0.0769(11) Uani 1 1 d . . . . .
H17 H 0.181375 0.187497 0.726812 0.092 Uiso 1 1 calc R . . . .
C16 C 0.2555(3) 0.19934(18) 0.5041(6) 0.0773(11) Uani 1 1 d . . . . .
H16 H 0.289320 0.238345 0.541991 0.093 Uiso 1 1 calc R . . . .
C19 C 0.4645(3) 0.00011(19) 1.3186(5) 0.0785(11) Uani 1 1 d . . . . .
H19A H 0.481139 0.044476 1.285047 0.094 Uiso 1 1 calc R . . . .
H19B H 0.433102 -0.022648 1.211781 0.094 Uiso 1 1 calc R . . . .
C20 C 0.4329(3) 0.0334(2) 1.6063(5) 0.0864(12) Uani 1 1 d . . . . .
H20A H 0.380361 0.032920 1.694052 0.104 Uiso 1 1 calc R . . . .
H20B H 0.448658 0.078554 1.579568 0.104 Uiso 1 1 calc R . . . .
O1 O 0.00148(17) 0.02270(10) 0.2860(3) 0.0583(6) Uani 1 1 d . . . . .
O2 O 0.38789(18) 0.00119(12) 1.4475(4) 0.0781(7) Uani 1 1 d . . . . .
N2 N 0.2730(2) 0.17628(14) 0.3421(4) 0.0673(8) Uani 1 1 d . . . . .
N1 N 0.16552(19) -0.02986(11) 0.3343(3) 0.0472(6) Uani 1 1 d . . . . .
H21 H 0.232489 -0.024836 0.378808 0.057 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
Cl2 C15 1.746(3) . ?
Cl1 C3 1.747(3) . ?
C6 C7 1.491(4) . ?
C6 C1 1.394(4) . ?
C6 C5 1.391(4) . ?
C14 C13 1.508(4) . ?
C14 C18 1.385(4) . ?
C14 C15 1.388(4) . ?
C7 C12 1.404(4) . ?
C7 C8 1.399(4) . ?
C12 C11 1.388(4) . ?
C12 N1 1.419(3) . ?
C13 O1 1.214(3) . ?
C13 N1 1.355(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.376(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.376(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.373(5) . ?
C3 C4 1.373(4) . ?
C15 N2 1.317(4) . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.359(5) . ?
C16 H16 0.9300 . ?
C16 N2 1.342(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.490(5) 3_658 ?
C19 O2 1.420(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 O2 1.420(4) . ?
N1 H21 0.8600 . ?

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 C6 C7 120.9(3) . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 C1 118.3(3) . . ?
C18 C14 C13 120.5(3) . . ?
C18 C14 C15 115.8(3) . . ?
C15 C14 C13 123.6(3) . . ?
C12 C7 C6 123.4(3) . . ?
C8 C7 C6 118.9(3) . . ?
C8 C7 C12 117.6(3) . . ?
C7 C12 N1 119.3(3) . . ?
C11 C12 C7 120.3(3) . . ?
C11 C12 N1 120.3(3) . . ?
O1 C13 C14 121.4(3) . . ?
O1 C13 N1 124.8(3) . . ?
N1 C13 C14 113.8(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C6 C1 H1 119.8 . . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.2 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.2 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C14 C18 H18 119.9 . . ?
C17 C18 C14 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C2 C3 Cl1 120.0(2) . . ?
C4 C3 Cl1 118.8(3) . . ?
C4 C3 C2 121.2(3) . . ?
C14 C15 Cl2 118.8(3) . . ?
N2 C15 Cl2 115.6(2) . . ?
N2 C15 C14 125.6(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C18 C17 H17 120.9 . . ?
C16 C17 C18 118.3(3) . . ?
C16 C17 H17 120.9 . . ?
C17 C16 H16 117.9 . . ?
N2 C16 C17 124.1(3) . . ?
N2 C16 H16 117.9 . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.6 3_658 . ?
C20 C19 H19B 109.6 3_658 . ?
O2 C19 H19A 109.6 . . ?
O2 C19 H19B 109.6 . . ?
O2 C19 C20 110.2(3) . 3_658 ?
C19 C20 H20A 109.7 3_658 . ?
C19 C20 H20B 109.7 3_658 . ?
H20A C20 H20B 108.2 . . ?
O2 C20 C19 109.9(3) . 3_658 ?
O2 C20 H20A 109.7 . . ?
O2 C20 H20B 109.7 . . ?
C20 O2 C19 110.6(3) . . ?
C15 N2 C16 116.0(3) . . ?
C12 N1 H21 117.1 . . ?
C13 N1 C12 125.7(2) . . ?
C13 N1 H21 117.1 . . ?

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
Cl2 C15 N2 C16 178.3(2) . . . . ?
Cl1 C3 C4 C5 179.1(2) . . . . ?
C6 C7 C12 C11 -177.5(3) . . . . ?
C6 C7 C12 N1 6.6(4) . . . . ?
C6 C7 C8 C9 174.9(3) . . . . ?
C6 C1 C2 C3 0.3(5) . . . . ?
C6 C5 C4 C3 1.2(4) . . . . ?
C14 C13 N1 C12 -175.4(2) . . . . ?
C14 C18 C17 C16 -0.4(5) . . . . ?
C14 C15 N2 C16 0.0(5) . . . . ?
C7 C6 C1 C2 174.2(3) . . . . ?
C7 C6 C5 C4 -174.9(3) . . . . ?
C7 C12 C11 C10 2.1(4) . . . . ?
C7 C12 N1 C13 -146.7(3) . . . . ?
C7 C8 C9 C10 3.3(5) . . . . ?
C12 C7 C8 C9 -2.6(4) . . . . ?
C12 C11 C10 C9 -1.5(5) . . . . ?
C13 C14 C18 C17 -176.7(3) . . . . ?
C13 C14 C15 Cl2 -1.5(4) . . . . ?
C13 C14 C15 N2 176.8(3) . . . . ?
C11 C12 N1 C13 37.4(4) . . . . ?
C11 C10 C9 C8 -1.2(5) . . . . ?
C1 C6 C7 C12 54.9(4) . . . . ?
C1 C6 C7 C8 -122.5(3) . . . . ?
C1 C6 C5 C4 -0.6(4) . . . . ?
C1 C2 C3 Cl1 -179.8(2) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C5 C6 C7 C12 -131.0(3) . . . . ?
C5 C6 C7 C8 51.7(4) . . . . ?
C5 C6 C1 C2 -0.1(4) . . . . ?
C8 C7 C12 C11 -0.1(4) . . . . ?
C8 C7 C12 N1 -176.0(2) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C18 C14 C13 O1 71.4(4) . . . . ?
C18 C14 C13 N1 -107.4(3) . . . . ?
C18 C14 C15 Cl2 -178.0(2) . . . . ?
C18 C14 C15 N2 0.3(5) . . . . ?
C18 C17 C16 N2 0.7(6) . . . . ?
C15 C14 C13 O1 -104.9(3) . . . . ?
C15 C14 C13 N1 76.2(3) . . . . ?
C15 C14 C18 C17 -0.1(5) . . . . ?
C17 C16 N2 C15 -0.5(5) . . . . ?
C19 C20 O2 C19 -58.1(4) 3_658 . . . ?
C20 C19 O2 C20 58.3(4) 3_658 . . . ?
O1 C13 N1 C12 5.7(4) . . . . ?
N1 C12 C11 C10 178.0(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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1900708'
loop_
_audit_author_name
_audit_author_address
'Zhonghua Li'
;Tianjin University
China
;

_audit_update_record             
;
2019-03-03 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2017-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 Cl2 N2 O, C2 H6 O1 S1'
_chemical_formula_sum            'C20 H18 Cl2 N2 O2 S'
_chemical_formula_weight         421.32
_chemical_absolute_configuration ?
_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'
S S 0.1246 0.1234 '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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   37.821(9)
_cell_length_b                   5.6762(13)
_cell_length_c                   18.699(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.084(5)
_cell_angle_gamma                90
_cell_volume                     3893.7(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5748
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  0.9470
_exptl_absorpt_correction_T_min  0.9138
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18755
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         3.332
_diffrn_ambient_temperature      133.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.754
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                7094
_reflns_number_total             7540
_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       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 2720 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         7540
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.031
_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)+(0.0407P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1 = N1'-H1'
 0.9 with sigma of 0.01
 S1"-C20" = S1"-C19" = S1'-C20' = S1'-C19'
 1.78 with sigma of 0.01
 S1"-O2" = S1'-O2'
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
S1" \\sim S1' \\sim C20" \\sim C19" \\sim C20' \\sim C19': within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(S1") \\sim Ueq, Uanis(S1') \\sim Ueq, Uanis(C20") \\sim Ueq, Uanis(C19")
\\sim Ueq, Uanis(C20') \\sim Ueq, Uanis(C19') \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(S1')=Sof(O2')=Sof(C20')=Sof(H20d)=Sof(H20e)=Sof(H20f)=Sof(C19')=Sof(H19d)=
 Sof(H19e)=Sof(H19f)=1-FVAR(1)
 Sof(S1")=Sof(O2")=Sof(C20")=Sof(H20a)=Sof(H20b)=Sof(H20c)=Sof(C19")=Sof(H19a)=
 Sof(H19b)=Sof(H19c)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C16(H16), C11(H11), C10(H10), C9(H9), C8(H8), C5(H5),
 C4(H4), C2(H2), C1(H1a), C18'(H18'), C17'(H17'), C16'(H16'), C11'(H11'),
 C10'(H10'), C9'(H9'), C8'(H8'), C1'(H1'a), C2'(H2'), C4'(H4'), C5'(H5')
5.b Idealised Me refined as rotating group:
 C20"(H20a,H20b,H20c), C19"(H19a,H19b,H19c), C20'(H20d,H20e,H20f), C19'(H19d,
 H19e,H19f), C19(H19g,H19h,H19i), C20(H20g,H20h,H20i)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl2 Cl 0.76329(2) 0.01886(12) 0.77488(3) 0.03221(16) Uani 1 1 d . . . . .
Cl1 Cl 0.59163(2) 0.75136(13) 1.00622(4) 0.03979(18) Uani 1 1 d . . . . .
Cl2' Cl 0.31612(2) 0.49856(12) 0.54605(4) 0.03149(15) Uani 1 1 d . . . . .
Cl1' Cl 0.48203(2) 1.23719(13) 0.94583(4) 0.03522(16) Uani 1 1 d . . . . .
O1 O 0.69140(5) 0.3760(4) 0.69660(10) 0.0323(4) Uani 1 1 d . . . . .
O1' O 0.38621(5) 0.8751(3) 0.53858(9) 0.0304(4) Uani 1 1 d . . . . .
N2 N 0.79101(6) 0.3150(4) 0.88004(12) 0.0283(5) Uani 1 1 d . . . . .
N1 N 0.67076(5) 0.1814(4) 0.78545(11) 0.0226(4) Uani 1 1 d D . . . .
N2' N 0.28658(6) 0.7915(5) 0.62138(13) 0.0359(6) Uani 1 1 d . . . . .
N1' N 0.40661(5) 0.6723(4) 0.64616(10) 0.0205(4) Uani 1 1 d D . . . .
C13 C 0.69491(7) 0.3119(5) 0.76023(13) 0.0215(5) Uani 1 1 d . . . . .
C14 C 0.72782(6) 0.3815(4) 0.81968(13) 0.0216(5) Uani 1 1 d . . . . .
C18 C 0.72695(7) 0.5698(5) 0.86615(14) 0.0281(5) Uani 1 1 d . . . . .
H18 H 0.705093 0.657022 0.861886 0.034 Uiso 1 1 calc R . . . .
C17 C 0.75803(8) 0.6302(5) 0.91874(15) 0.0331(6) Uani 1 1 d . . . . .
H17 H 0.757896 0.759390 0.950976 0.040 Uiso 1 1 calc R . . . .
C16 C 0.78933(8) 0.4997(5) 0.92369(14) 0.0304(6) Uani 1 1 d . . . . .
H16 H 0.810696 0.542861 0.959763 0.036 Uiso 1 1 calc R . . . .
C15 C 0.76081(7) 0.2618(5) 0.83054(13) 0.0236(5) Uani 1 1 d . . . . .
C12 C 0.63817(7) 0.0861(5) 0.73892(13) 0.0234(5) Uani 1 1 d . . . . .
C11 C 0.64159(8) -0.0740(6) 0.68516(15) 0.0332(6) Uani 1 1 d . . . . .
H11 H 0.665066 -0.112772 0.678796 0.040 Uiso 1 1 calc R . . . .
C10 C 0.61074(9) -0.1781(6) 0.64043(16) 0.0392(7) Uani 1 1 d . . . . .
H10 H 0.612994 -0.285002 0.602682 0.047 Uiso 1 1 calc R . . . .
C9 C 0.57701(9) -0.1251(6) 0.65132(16) 0.0384(7) Uani 1 1 d . . . . .
H9 H 0.555844 -0.194114 0.620456 0.046 Uiso 1 1 calc R . . . .
C8 C 0.57360(7) 0.0271(5) 0.70654(15) 0.0315(6) Uani 1 1 d . . . . .
H8 H 0.550112 0.057364 0.714295 0.038 Uiso 1 1 calc R . . . .
C7 C 0.60417(7) 0.1386(5) 0.75169(14) 0.0240(5) Uani 1 1 d . . . . .
C6 C 0.59964(6) 0.2986(5) 0.81147(14) 0.0235(5) Uani 1 1 d . . . . .
C5 C 0.57849(7) 0.2289(5) 0.85959(15) 0.0267(6) Uani 1 1 d . . . . .
H5 H 0.565933 0.082617 0.851637 0.032 Uiso 1 1 calc R . . . .
C4 C 0.57544(7) 0.3684(5) 0.91860(16) 0.0305(6) Uani 1 1 d . . . . .
H4 H 0.561181 0.318085 0.951153 0.037 Uiso 1 1 calc R . . . .
C3 C 0.59336(7) 0.5806(5) 0.92923(15) 0.0286(6) Uani 1 1 d . . . . .
C2 C 0.61350(7) 0.6610(5) 0.88150(15) 0.0286(6) Uani 1 1 d . . . . .
H2 H 0.625066 0.810678 0.888708 0.034 Uiso 1 1 calc R . . . .
C1 C 0.61644(7) 0.5191(5) 0.82312(14) 0.0257(5) Uani 1 1 d . . . . .
H1A H 0.630219 0.572951 0.790116 0.031 Uiso 1 1 calc R . . . .
C13' C 0.38267(6) 0.8054(4) 0.59805(13) 0.0198(5) Uani 1 1 d . . . . .
C14' C 0.34951(6) 0.8689(4) 0.62535(13) 0.0217(5) Uani 1 1 d . . . . .
C18' C 0.34925(8) 1.0589(5) 0.67140(14) 0.0290(6) Uani 1 1 d . . . . .
H18' H 0.370707 1.149521 0.689136 0.035 Uiso 1 1 calc R . . . .
C17' C 0.31731(8) 1.1158(6) 0.69146(15) 0.0357(7) Uani 1 1 d . . . . .
H17' H 0.316423 1.247049 0.722494 0.043 Uiso 1 1 calc R . . . .
C16' C 0.28695(9) 0.9781(6) 0.66546(18) 0.0384(7) Uani 1 1 d . . . . .
H16' H 0.265157 1.017249 0.679476 0.046 Uiso 1 1 calc R . . . .
C15' C 0.31719(7) 0.7420(5) 0.60346(13) 0.0245(5) Uani 1 1 d . . . . .
C12' C 0.43928(6) 0.5791(5) 0.63133(13) 0.0203(5) Uani 1 1 d . . . . .
C11' C 0.43627(8) 0.4252(5) 0.57284(14) 0.0283(6) Uani 1 1 d . . . . .
H11' H 0.413008 0.391716 0.541503 0.034 Uiso 1 1 calc R . . . .
C10' C 0.46738(8) 0.3190(5) 0.55981(15) 0.0325(6) Uani 1 1 d . . . . .
H10' H 0.465424 0.214923 0.519236 0.039 Uiso 1 1 calc R . . . .
C9' C 0.50096(8) 0.3658(5) 0.60611(16) 0.0338(7) Uani 1 1 d . . . . .
H9' H 0.522257 0.295638 0.597075 0.041 Uiso 1 1 calc R . . . .
C8' C 0.50371(7) 0.5149(5) 0.66575(15) 0.0278(6) Uani 1 1 d . . . . .
H8' H 0.526949 0.541445 0.698113 0.033 Uiso 1 1 calc R . . . .
C7' C 0.47321(7) 0.6274(4) 0.67960(13) 0.0212(5) Uani 1 1 d . . . . .
C6' C 0.47683(6) 0.7854(4) 0.74408(14) 0.0210(5) Uani 1 1 d . . . . .
C1' C 0.45988(7) 1.0063(4) 0.73815(15) 0.0251(5) Uani 1 1 d . . . . .
H1'A H 0.446750 1.060790 0.691150 0.030 Uiso 1 1 calc R . . . .
C2' C 0.46192(7) 1.1465(4) 0.79954(15) 0.0259(5) Uani 1 1 d . . . . .
H2' H 0.450132 1.295507 0.794856 0.031 Uiso 1 1 calc R . . . .
C3' C 0.48131(7) 1.0673(5) 0.86784(15) 0.0250(5) Uani 1 1 d . . . . .
C4' C 0.49954(7) 0.8540(5) 0.87558(15) 0.0256(5) Uani 1 1 d . . . . .
H4' H 0.513326 0.803273 0.922532 0.031 Uiso 1 1 calc R . . . .
C5' C 0.49733(7) 0.7154(5) 0.81354(14) 0.0245(5) Uani 1 1 d . . . . .
H5' H 0.510034 0.569664 0.818345 0.029 Uiso 1 1 calc R . . . .
S1" S 0.70910(2) 0.15972(18) 0.00115(4) 0.0296(3) Uani 0.773(3) 1 d D U P A 1
O2" O 0.6901(4) 0.034(2) -0.0678(5) 0.039(2) Uani 0.773(3) 1 d D . P A 1
C20" C 0.7064(3) -0.0364(19) 0.0735(4) 0.051(3) Uani 0.773(3) 1 d D U P A 1
H20A H 0.681444 -0.097244 0.065273 0.077 Uiso 0.773(3) 1 calc GR . P A 1
H20B H 0.712827 0.047650 0.120713 0.077 Uiso 0.773(3) 1 calc GR . P A 1
H20C H 0.723290 -0.167725 0.074590 0.077 Uiso 0.773(3) 1 calc GR . P A 1
C19" C 0.67702(16) 0.3688(10) 0.0178(4) 0.0509(15) Uani 0.773(3) 1 d D U P A 1
H19A H 0.675227 0.500373 -0.016840 0.076 Uiso 0.773(3) 1 calc GR . P A 1
H19B H 0.685028 0.427780 0.068416 0.076 Uiso 0.773(3) 1 calc GR . P A 1
H19C H 0.653111 0.293470 0.010973 0.076 Uiso 0.773(3) 1 calc GR . P A 1
S1' S 0.67777(10) 0.1220(9) 0.0048(2) 0.0571(14) Uani 0.227(3) 1 d D U P A 2
O2' O 0.6851(14) 0.045(8) -0.0667(15) 0.058(11) Uani 0.227(3) 1 d D . P A 2
C20' C 0.7131(9) 0.016(7) 0.0783(18) 0.051(7) Uani 0.227(3) 1 d D U P A 2
H20D H 0.705048 -0.129609 0.097946 0.077 Uiso 0.227(3) 1 calc GR . P A 2
H20E H 0.718869 0.134523 0.117424 0.077 Uiso 0.227(3) 1 calc GR . P A 2
H20F H 0.734814 -0.016917 0.060212 0.077 Uiso 0.227(3) 1 calc GR . P A 2
C19' C 0.6911(7) 0.423(3) 0.0185(19) 0.071(6) Uani 0.227(3) 1 d D U P A 2
H19D H 0.717220 0.437766 0.021138 0.106 Uiso 0.227(3) 1 calc GR . P A 2
H19E H 0.686207 0.480004 0.064680 0.106 Uiso 0.227(3) 1 calc GR . P A 2
H19F H 0.677247 0.517870 -0.022696 0.106 Uiso 0.227(3) 1 calc GR . P A 2
S1 S 0.86603(2) 0.12669(12) 0.81820(3) 0.02549(14) Uani 1 1 d . . . . .
O2 O 0.88923(6) 0.0070(3) 0.77363(10) 0.0316(4) Uani 1 1 d . . . . .
C19 C 0.86123(8) -0.0817(6) 0.88632(15) 0.0342(6) Uani 1 1 d . . . . .
H19G H 0.847525 -0.218560 0.862287 0.051 Uiso 1 1 calc GR . . . .
H19H H 0.848124 -0.009044 0.919838 0.051 Uiso 1 1 calc GR . . . .
H19I H 0.885416 -0.132419 0.914330 0.051 Uiso 1 1 calc GR . . . .
C20 C 0.89591(10) 0.3217(6) 0.87769(18) 0.0443(8) Uani 1 1 d . . . . .
H20G H 0.918456 0.238496 0.901171 0.066 Uiso 1 1 calc GR . . . .
H20H H 0.884225 0.379481 0.915679 0.066 Uiso 1 1 calc GR . . . .
H20I H 0.901622 0.455145 0.849194 0.066 Uiso 1 1 calc GR . . . .
H1' H 0.4004(7) 0.636(5) 0.6872(10) 0.022(7) Uiso 1 1 d D . . . .
H1 H 0.6753(10) 0.149(6) 0.8334(8) 0.052(10) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C15 1.744(3) . ?
Cl1 C3 1.750(3) . ?
Cl2' C15' 1.744(3) . ?
Cl1' C3' 1.743(3) . ?
O1 C13 1.220(3) . ?
O1' C13' 1.218(3) . ?
N2 C16 1.340(4) . ?
N2 C15 1.318(3) . ?
N1 C13 1.347(3) . ?
N1 C12 1.431(3) . ?
N1 H1 0.889(13) . ?
N2' C16' 1.340(4) . ?
N2' C15' 1.312(3) . ?
N1' C13' 1.343(3) . ?
N1' C12' 1.432(3) . ?
N1' H1' 0.881(13) . ?
C13 C14 1.506(3) . ?
C14 C18 1.383(4) . ?
C14 C15 1.391(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.380(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.380(4) . ?
C16 H16 0.9500 . ?
C12 C11 1.384(4) . ?
C12 C7 1.396(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.391(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.373(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.376(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.405(3) . ?
C7 C6 1.482(4) . ?
C6 C5 1.399(4) . ?
C6 C1 1.397(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.372(4) . ?
C3 C2 1.384(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.383(4) . ?
C1 H1A 0.9500 . ?
C13' C14' 1.508(3) . ?
C14' C18' 1.381(4) . ?
C14' C15' 1.392(4) . ?
C18' H18' 0.9500 . ?
C18' C17' 1.387(4) . ?
C17' H17' 0.9500 . ?
C17' C16' 1.377(5) . ?
C16' H16' 0.9500 . ?
C12' C11' 1.383(4) . ?
C12' C7' 1.405(3) . ?
C11' H11' 0.9500 . ?
C11' C10' 1.395(4) . ?
C10' H10' 0.9500 . ?
C10' C9' 1.378(4) . ?
C9' H9' 0.9500 . ?
C9' C8' 1.383(4) . ?
C8' H8' 0.9500 . ?
C8' C7' 1.397(3) . ?
C7' C6' 1.482(4) . ?
C6' C1' 1.400(4) . ?
C6' C5' 1.398(3) . ?
C1' H1'A 0.9500 . ?
C1' C2' 1.384(4) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.384(4) . ?
C3' C4' 1.384(4) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.387(4) . ?
C5' H5' 0.9500 . ?
S1" O2" 1.497(9) . ?
S1" C20" 1.775(7) . ?
S1" C19" 1.778(5) . ?
C20" H20A 0.9800 . ?
C20" H20B 0.9800 . ?
C20" H20C 0.9800 . ?
C19" H19A 0.9800 . ?
C19" H19B 0.9800 . ?
C19" H19C 0.9800 . ?
S1' O2' 1.494(13) . ?
S1' C20' 1.773(13) . ?
S1' C19' 1.784(13) . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
S1 O2 1.511(2) . ?
S1 C19 1.780(3) . ?
S1 C20 1.769(3) . ?
C19 H19G 0.9800 . ?
C19 H19H 0.9800 . ?
C19 H19I 0.9800 . ?
C20 H20G 0.9800 . ?
C20 H20H 0.9800 . ?
C20 H20I 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
C15 N2 C16 116.5(2) . . ?
C13 N1 C12 123.5(2) . . ?
C13 N1 H1 119(2) . . ?
C12 N1 H1 118(2) . . ?
C15' N2' C16' 116.7(3) . . ?
C13' N1' C12' 123.45(19) . . ?
C13' N1' H1' 116.0(18) . . ?
C12' N1' H1' 120.4(18) . . ?
O1 C13 N1 125.7(2) . . ?
O1 C13 C14 121.1(2) . . ?
N1 C13 C14 113.2(2) . . ?
C18 C14 C13 121.6(2) . . ?
C18 C14 C15 116.3(2) . . ?
C15 C14 C13 122.0(2) . . ?
C14 C18 H18 120.2 . . ?
C17 C18 C14 119.6(2) . . ?
C17 C18 H18 120.2 . . ?
C18 C17 H17 120.6 . . ?
C18 C17 C16 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
N2 C16 C17 123.1(3) . . ?
N2 C16 H16 118.5 . . ?
C17 C16 H16 118.5 . . ?
N2 C15 Cl2 115.90(19) . . ?
N2 C15 C14 125.7(2) . . ?
C14 C15 Cl2 118.39(19) . . ?
C11 C12 N1 118.1(2) . . ?
C11 C12 C7 121.1(2) . . ?
C7 C12 N1 120.6(2) . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10 120.3 . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C9 C8 H8 119.3 . . ?
C9 C8 C7 121.3(3) . . ?
C7 C8 H8 119.3 . . ?
C12 C7 C8 117.3(3) . . ?
C12 C7 C6 122.7(2) . . ?
C8 C7 C6 120.0(2) . . ?
C5 C6 C7 120.1(2) . . ?
C1 C6 C7 122.3(2) . . ?
C1 C6 C5 117.6(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.6 . . ?
C4 C3 Cl1 119.3(2) . . ?
C4 C3 C2 121.7(3) . . ?
C2 C3 Cl1 119.0(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C6 C1 H1A 119.2 . . ?
C2 C1 C6 121.6(2) . . ?
C2 C1 H1A 119.2 . . ?
O1' C13' N1' 126.0(2) . . ?
O1' C13' C14' 121.1(2) . . ?
N1' C13' C14' 112.8(2) . . ?
C18' C14' C13' 122.0(2) . . ?
C18' C14' C15' 116.6(2) . . ?
C15' C14' C13' 121.3(2) . . ?
C14' C18' H18' 120.4 . . ?
C14' C18' C17' 119.3(3) . . ?
C17' C18' H18' 120.4 . . ?
C18' C17' H17' 120.7 . . ?
C16' C17' C18' 118.6(3) . . ?
C16' C17' H17' 120.7 . . ?
N2' C16' C17' 123.3(3) . . ?
N2' C16' H16' 118.4 . . ?
C17' C16' H16' 118.4 . . ?
N2' C15' Cl2' 115.9(2) . . ?
N2' C15' C14' 125.5(3) . . ?
C14' C15' Cl2' 118.57(19) . . ?
C11' C12' N1' 118.6(2) . . ?
C11' C12' C7' 121.2(2) . . ?
C7' C12' N1' 120.0(2) . . ?
C12' C11' H11' 120.0 . . ?
C12' C11' C10' 120.0(3) . . ?
C10' C11' H11' 120.0 . . ?
C11' C10' H10' 120.2 . . ?
C9' C10' C11' 119.6(3) . . ?
C9' C10' H10' 120.2 . . ?
C10' C9' H9' 119.9 . . ?
C10' C9' C8' 120.1(2) . . ?
C8' C9' H9' 119.9 . . ?
C9' C8' H8' 119.2 . . ?
C9' C8' C7' 121.7(2) . . ?
C7' C8' H8' 119.2 . . ?
C12' C7' C6' 122.0(2) . . ?
C8' C7' C12' 117.3(2) . . ?
C8' C7' C6' 120.7(2) . . ?
C1' C6' C7' 121.8(2) . . ?
C5' C6' C7' 120.3(2) . . ?
C5' C6' C1' 117.9(2) . . ?
C6' C1' H1'A 119.4 . . ?
C2' C1' C6' 121.2(2) . . ?
C2' C1' H1'A 119.4 . . ?
C1' C2' H2' 120.4 . . ?
C1' C2' C3' 119.3(2) . . ?
C3' C2' H2' 120.4 . . ?
C2' C3' Cl1' 119.3(2) . . ?
C4' C3' Cl1' 119.4(2) . . ?
C4' C3' C2' 121.3(2) . . ?
C3' C4' H4' 120.6 . . ?
C3' C4' C5' 118.8(2) . . ?
C5' C4' H4' 120.6 . . ?
C6' C5' H5' 119.2 . . ?
C4' C5' C6' 121.5(2) . . ?
C4' C5' H5' 119.2 . . ?
O2" S1" C20" 104.6(6) . . ?
O2" S1" C19" 105.4(5) . . ?
C20" S1" C19" 96.7(5) . . ?
S1" C20" H20A 109.5 . . ?
S1" C20" H20B 109.5 . . ?
S1" C20" H20C 109.5 . . ?
H20A C20" H20B 109.5 . . ?
H20A C20" H20C 109.5 . . ?
H20B C20" H20C 109.5 . . ?
S1" C19" H19A 109.5 . . ?
S1" C19" H19B 109.5 . . ?
S1" C19" H19C 109.5 . . ?
H19A C19" H19B 109.5 . . ?
H19A C19" H19C 109.5 . . ?
H19B C19" H19C 109.5 . . ?
O2' S1' C20' 109(3) . . ?
O2' S1' C19' 107(2) . . ?
C20' S1' C19' 94.7(17) . . ?
S1' C20' H20D 109.5 . . ?
S1' C20' H20E 109.5 . . ?
S1' C20' H20F 109.5 . . ?
H20D C20' H20E 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
S1' C19' H19D 109.5 . . ?
S1' C19' H19E 109.5 . . ?
S1' C19' H19F 109.5 . . ?
H19D C19' H19E 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
O2 S1 C19 105.66(13) . . ?
O2 S1 C20 105.08(15) . . ?
C20 S1 C19 97.28(16) . . ?
S1 C19 H19G 109.5 . . ?
S1 C19 H19H 109.5 . . ?
S1 C19 H19I 109.5 . . ?
H19G C19 H19H 109.5 . . ?
H19G C19 H19I 109.5 . . ?
H19H C19 H19I 109.5 . . ?
S1 C20 H20G 109.5 . . ?
S1 C20 H20H 109.5 . . ?
S1 C20 H20I 109.5 . . ?
H20G C20 H20H 109.5 . . ?
H20G C20 H20I 109.5 . . ?
H20H C20 H20I 109.5 . . ?

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
N1' H1' O2 0.881(13) 1.911(14) 2.785(3) 171(3) 3_455
N1 H1 O2" 0.889(13) 1.912(19) 2.791(11) 170(4) 1_556
N1 H1 O2' 0.889(13) 1.91(4) 2.79(3) 174(4) 1_556

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 C3 C2 C1 176.39(19) . . . . ?
Cl1' C3' C4' C5' 177.0(2) . . . . ?
O1 C13 C14 C18 97.7(3) . . . . ?
O1 C13 C14 C15 -81.7(3) . . . . ?
O1' C13' C14' C18' -94.8(3) . . . . ?
O1' C13' C14' C15' 83.3(3) . . . . ?
N1 C13 C14 C18 -80.9(3) . . . . ?
N1 C13 C14 C15 99.7(3) . . . . ?
N1 C12 C11 C10 177.6(3) . . . . ?
N1 C12 C7 C8 -176.2(2) . . . . ?
N1 C12 C7 C6 1.9(4) . . . . ?
N1' C13' C14' C18' 84.2(3) . . . . ?
N1' C13' C14' C15' -97.6(3) . . . . ?
N1' C12' C11' C10' -175.8(2) . . . . ?
N1' C12' C7' C8' 174.5(2) . . . . ?
N1' C12' C7' C6' -3.7(4) . . . . ?
C13 N1 C12 C11 62.1(4) . . . . ?
C13 N1 C12 C7 -123.2(3) . . . . ?
C13 C14 C18 C17 -178.5(2) . . . . ?
C13 C14 C15 Cl2 -1.9(3) . . . . ?
C13 C14 C15 N2 178.3(2) . . . . ?
C14 C18 C17 C16 -0.2(4) . . . . ?
C18 C14 C15 Cl2 178.7(2) . . . . ?
C18 C14 C15 N2 -1.1(4) . . . . ?
C18 C17 C16 N2 -0.5(4) . . . . ?
C16 N2 C15 Cl2 -179.3(2) . . . . ?
C16 N2 C15 C14 0.5(4) . . . . ?
C15 N2 C16 C17 0.3(4) . . . . ?
C15 C14 C18 C17 0.9(4) . . . . ?
C12 N1 C13 O1 4.2(4) . . . . ?
C12 N1 C13 C14 -177.2(2) . . . . ?
C12 C11 C10 C9 -1.6(5) . . . . ?
C12 C7 C6 C5 -130.6(3) . . . . ?
C12 C7 C6 C1 48.2(3) . . . . ?
C11 C12 C7 C8 -1.6(4) . . . . ?
C11 C12 C7 C6 176.5(2) . . . . ?
C11 C10 C9 C8 -0.9(5) . . . . ?
C10 C9 C8 C7 2.1(4) . . . . ?
C9 C8 C7 C12 -0.9(4) . . . . ?
C9 C8 C7 C6 -179.0(2) . . . . ?
C8 C7 C6 C5 47.4(3) . . . . ?
C8 C7 C6 C1 -133.8(3) . . . . ?
C7 C12 C11 C10 2.9(4) . . . . ?
C7 C6 C5 C4 176.2(2) . . . . ?
C7 C6 C1 C2 -176.5(2) . . . . ?
C6 C5 C4 C3 0.7(4) . . . . ?
C5 C6 C1 C2 2.3(4) . . . . ?
C5 C4 C3 Cl1 -176.7(2) . . . . ?
C5 C4 C3 C2 1.8(4) . . . . ?
C4 C3 C2 C1 -2.1(4) . . . . ?
C3 C2 C1 C6 0.0(4) . . . . ?
C1 C6 C5 C4 -2.6(4) . . . . ?
C13' N1' C12' C11' -61.5(3) . . . . ?
C13' N1' C12' C7' 124.3(3) . . . . ?
C13' C14' C18' C17' 176.6(2) . . . . ?
C13' C14' C15' Cl2' 2.4(3) . . . . ?
C13' C14' C15' N2' -176.4(2) . . . . ?
C14' C18' C17' C16' 0.9(4) . . . . ?
C18' C14' C15' Cl2' -179.36(19) . . . . ?
C18' C14' C15' N2' 1.8(4) . . . . ?
C18' C17' C16' N2' -0.2(4) . . . . ?
C16' N2' C15' Cl2' -180.0(2) . . . . ?
C16' N2' C15' C14' -1.1(4) . . . . ?
C15' N2' C16' C17' 0.3(4) . . . . ?
C15' C14' C18' C17' -1.6(4) . . . . ?
C12' N1' C13' O1' -4.4(4) . . . . ?
C12' N1' C13' C14' 176.6(2) . . . . ?
C12' C11' C10' C9' 0.9(4) . . . . ?
C12' C7' C6' C1' -47.7(3) . . . . ?
C12' C7' C6' C5' 131.7(3) . . . . ?
C11' C12' C7' C8' 0.4(4) . . . . ?
C11' C12' C7' C6' -177.9(2) . . . . ?
C11' C10' C9' C8' 0.9(4) . . . . ?
C10' C9' C8' C7' -2.1(4) . . . . ?
C9' C8' C7' C12' 1.4(4) . . . . ?
C9' C8' C7' C6' 179.7(2) . . . . ?
C8' C7' C6' C1' 134.1(3) . . . . ?
C8' C7' C6' C5' -46.5(3) . . . . ?
C7' C12' C11' C10' -1.6(4) . . . . ?
C7' C6' C1' C2' 176.5(2) . . . . ?
C7' C6' C5' C4' -176.4(2) . . . . ?
C6' C1' C2' C3' 0.5(4) . . . . ?
C1' C6' C5' C4' 3.1(4) . . . . ?
C1' C2' C3' Cl1' -176.87(19) . . . . ?
C1' C2' C3' C4' 1.9(4) . . . . ?
C2' C3' C4' C5' -1.7(4) . . . . ?
C3' C4' C5' C6' -0.8(4) . . . . ?
C5' C6' C1' C2' -2.9(4) . . . . ?
_olex2_submission_special_instructions 'No special instructions were received'
