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

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

data_01173brscz_0m
_database_code_depnum_ccdc_archive 'CCDC 2202707'
loop_
_audit_author_name
_audit_author_address
'Wang Zhaoyu'
;Nanjing University of Technology
China
;
_audit_update_record             
;
2022-08-22 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 Br N O S'
_chemical_formula_sum            'C17 H10 Br N O S'
_chemical_formula_weight         356.23
_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'
Br Br -0.2901 2.4595 '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'

_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                   7.8966(4)
_cell_length_b                   7.7464(4)
_cell_length_c                   23.3386(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.192(2)
_cell_angle_gamma                90
_cell_volume                     1419.30(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.16
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.040
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4812
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0883 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.6456.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15579
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_min         2.594
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2182
_reflns_number_total             2890
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.047
_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)+(0.0315P)²+1.3524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_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
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br01 Br 0.01517(4) 0.67624(5) 0.30164(2) 0.05918(15) Uani 1 1 d . . . . .
S002 S 0.54659(10) 0.57037(12) 0.27855(4) 0.0509(2) Uani 1 1 d . . . . .
N003 N 0.3296(3) 0.5652(3) 0.41584(9) 0.0362(5) Uani 1 1 d . . . . .
O004 O 0.4939(3) 0.7909(3) 0.39358(10) 0.0560(6) Uani 1 1 d . . . . .
C005 C 0.2626(3) 0.3943(4) 0.40736(12) 0.0353(6) Uani 1 1 d . . . . .
C006 C 0.3770(4) 0.6235(4) 0.31552(12) 0.0371(6) Uani 1 1 d . . . . .
C007 C 0.2316(4) 0.6259(4) 0.27895(13) 0.0389(7) Uani 1 1 d . . . . .
C008 C 0.3158(4) 0.6130(4) 0.47424(12) 0.0369(6) Uani 1 1 d . . . . .
C009 C 0.4065(4) 0.6678(4) 0.37778(12) 0.0390(7) Uani 1 1 d . . . . .
C00A C 0.2375(4) 0.4769(4) 0.50095(12) 0.0396(7) Uani 1 1 d . . . . .
C00B C 0.2073(4) 0.3390(4) 0.45920(12) 0.0379(7) Uani 1 1 d . . . . .
C00C C 0.2553(4) 0.2852(4) 0.36015(13) 0.0433(7) Uani 1 1 d . . . . .
H00C H 0.2943 0.3204 0.3258 0.052 Uiso 1 1 calc R . . . .
C00D C 0.2539(4) 0.5838(4) 0.22153(13) 0.0465(8) Uani 1 1 d . . . . .
H00D H 0.1661 0.5804 0.1916 0.056 Uiso 1 1 calc R . . . .
C00E C 0.4181(5) 0.5493(4) 0.21532(13) 0.0517(8) Uani 1 1 d . . . . .
H00E H 0.4569 0.5176 0.1806 0.062 Uiso 1 1 calc R . . . .
C00F C 0.1882(4) 0.1225(4) 0.36582(14) 0.0472(8) Uani 1 1 d . . . . .
H00F H 0.1811 0.0477 0.3345 0.057 Uiso 1 1 calc R . . . .
C00G C 0.3627(4) 0.7647(4) 0.50308(13) 0.0474(8) Uani 1 1 d . . . . .
H00G H 0.4149 0.8543 0.4851 0.057 Uiso 1 1 calc R . . . .
C00H C 0.1413(4) 0.1746(4) 0.46348(15) 0.0505(8) Uani 1 1 d . . . . .
H00H H 0.1039 0.1372 0.4978 0.061 Uiso 1 1 calc R . . . .
C00I C 0.3280(5) 0.7767(5) 0.56000(14) 0.0571(9) Uani 1 1 d . . . . .
H00I H 0.3583 0.8767 0.5807 0.069 Uiso 1 1 calc R . . . .
C00J C 0.2040(4) 0.4931(5) 0.55800(13) 0.0521(8) Uani 1 1 d . . . . .
H00J H 0.1518 0.4040 0.5762 0.063 Uiso 1 1 calc R . . . .
C00K C 0.1315(4) 0.0675(4) 0.41655(15) 0.0527(8) Uani 1 1 d . . . . .
H00K H 0.0864 -0.0429 0.4189 0.063 Uiso 1 1 calc R . . . .
C00L C 0.2495(5) 0.6436(5) 0.58683(14) 0.0617(10) Uani 1 1 d . . . . .
H00L H 0.2273 0.6563 0.6249 0.074 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
Br01 C007 1.884(3) . ?
S002 C006 1.720(3) . ?
S002 C00E 1.706(3) . ?
N003 C005 1.432(4) . ?
N003 C008 1.428(3) . ?
N003 C009 1.380(4) . ?
O004 C009 1.211(4) . ?
C005 C00B 1.397(4) . ?
C005 C00C 1.385(4) . ?
C006 C007 1.355(4) . ?
C006 C009 1.487(4) . ?
C007 C00D 1.408(4) . ?
C008 C00A 1.402(4) . ?
C008 C00G 1.385(4) . ?
C00A C00B 1.448(4) . ?
C00A C00J 1.391(4) . ?
C00B C00H 1.384(4) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.379(4) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.347(5) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00K 1.378(5) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.388(5) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.370(5) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.387(6) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.374(5) . ?
C00K H00K 0.9300 . ?
C00L H00L 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
C00E S002 C006 91.96(16) . . ?
C008 N003 C005 107.8(2) . . ?
C009 N003 C005 128.7(2) . . ?
C009 N003 C008 123.3(2) . . ?
C00B C005 N003 108.0(2) . . ?
C00C C005 N003 131.1(3) . . ?
C00C C005 C00B 120.8(3) . . ?
C007 C006 S002 109.9(2) . . ?
C007 C006 C009 130.2(3) . . ?
C009 C006 S002 119.8(2) . . ?
C006 C007 Br01 124.0(2) . . ?
C006 C007 C00D 114.3(3) . . ?
C00D C007 Br01 121.7(2) . . ?
C00A C008 N003 108.2(3) . . ?
C00G C008 N003 129.8(3) . . ?
C00G C008 C00A 122.0(3) . . ?
N003 C009 C006 117.6(3) . . ?
O004 C009 N003 122.2(3) . . ?
O004 C009 C006 120.2(3) . . ?
C008 C00A C00B 107.7(3) . . ?
C00J C00A C008 119.8(3) . . ?
C00J C00A C00B 132.6(3) . . ?
C005 C00B C00A 108.2(3) . . ?
C00H C00B C005 120.0(3) . . ?
C00H C00B C00A 131.8(3) . . ?
C005 C00C H00C 121.1 . . ?
C00F C00C C005 117.7(3) . . ?
C00F C00C H00C 121.1 . . ?
C007 C00D H00D 124.2 . . ?
C00E C00D C007 111.7(3) . . ?
C00E C00D H00D 124.2 . . ?
S002 C00E H00E 123.9 . . ?
C00D C00E S002 112.2(2) . . ?
C00D C00E H00E 123.9 . . ?
C00C C00F H00F 119.0 . . ?
C00K C00F C00C 121.9(3) . . ?
C00K C00F H00F 119.0 . . ?
C008 C00G H00G 121.6 . . ?
C008 C00G C00I 116.9(3) . . ?
C00I C00G H00G 121.6 . . ?
C00B C00H H00H 120.4 . . ?
C00K C00H C00B 119.2(3) . . ?
C00K C00H H00H 120.4 . . ?
C00G C00I H00I 119.1 . . ?
C00L C00I C00G 121.7(3) . . ?
C00L C00I H00I 119.1 . . ?
C00A C00J H00J 120.7 . . ?
C00L C00J C00A 118.6(3) . . ?
C00L C00J H00J 120.7 . . ?
C00F C00K H00K 119.8 . . ?
C00H C00K C00F 120.3(3) . . ?
C00H C00K H00K 119.9 . . ?
C00I C00L H00L 119.5 . . ?
C00J C00L C00I 121.0(3) . . ?
C00J C00L H00L 119.5 . . ?

_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_zyy
_database_code_depnum_ccdc_archive 'CCDC 2203143'
loop_
_audit_author_name
_audit_author_address
'Wang Zhaoyu'
;Nanjing University of Technology
China
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 F N O S'
_chemical_formula_sum            'C17 H10 F N O S'
_chemical_formula_weight         295.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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'
F F 0.0171 0.0103 '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'

_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   18.9441(17)
_cell_length_b                   5.3279(5)
_cell_length_c                   13.3123(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.087(8)
_cell_angle_gamma                90
_cell_volume                     1330.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1000
_cell_measurement_theta_min      2.2890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4869
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.764
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.253
_diffrn_reflns_theta_min         2.482
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  30.50   0.50   20.00    --   20.00  54.00  30.00   85
  2  ω    -73.00 -48.00   0.50   20.00    --   20.00  54.00 120.00   50
  3  ω    -43.00  40.00   0.50   20.00    --   20.00  54.00 120.00  166
  4  ω     49.00  75.00   0.50   20.00    --   20.00  54.00 120.00   52
  5  ω    -72.00 -47.00   0.50   20.00    --   20.00  54.00 -30.00   50
  6  ω     -7.00 105.00   0.50   20.00    --   20.00  54.00 -30.00  224
  7  ω    -14.00  37.00   0.50   20.00    --   20.00  54.00  60.00  102
  8  ω     80.00 105.00   0.50   20.00    --   20.00  54.00  60.00   50
  9  ω    -66.00 -40.00   0.50   20.00    --   20.00  54.00  30.00   52
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0169588000
_diffrn_orient_matrix_UB_12      0.0012039000
_diffrn_orient_matrix_UB_13      -0.0509970000
_diffrn_orient_matrix_UB_21      -0.0335885000
_diffrn_orient_matrix_UB_22      -0.0162031000
_diffrn_orient_matrix_UB_23      0.0169210000
_diffrn_orient_matrix_UB_31      -0.0039448000
_diffrn_orient_matrix_UB_32      0.1321400000
_diffrn_orient_matrix_UB_33      0.0025800000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.455
_reflns_Friedel_fraction_full    0.679
_reflns_Friedel_fraction_max     0.531
_reflns_number_gt                2036
_reflns_number_total             3037
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      0.960
_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)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C13(H13), C5(H5), C12(H12), C11(H11), C4(H4), C3(H3), C10(H10),
 C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S16 S 0.72003(5) -0.0445(2) 0.08207(6) 0.0514(3) Uani 1 1 d . . . . .
F1 F 0.78202(10) 0.4755(5) 0.27215(16) 0.0648(7) Uani 1 1 d . . . . .
O15 O 0.60132(12) 0.3436(5) 0.06455(15) 0.0480(7) Uani 1 1 d . . . . .
N9 N 0.61733(13) 0.4550(7) 0.23121(17) 0.0352(6) Uani 1 1 d . . . . .
C6 C 0.55596(17) 0.7246(7) 0.3222(2) 0.0332(8) Uani 1 1 d . . . . .
C8 C 0.63472(16) 0.3894(6) 0.3368(2) 0.0324(8) Uani 1 1 d . . . . .
C14 C 0.63865(18) 0.3356(7) 0.1472(2) 0.0373(8) Uani 1 1 d . . . . .
C1 C 0.56771(17) 0.6547(7) 0.2241(2) 0.0346(8) Uani 1 1 d . . . . .
C7 C 0.59785(18) 0.5560(7) 0.3922(2) 0.0347(8) Uani 1 1 d . . . . .
C2 C 0.53470(17) 0.7813(8) 0.1388(2) 0.0447(10) Uani 1 1 d . . . . .
H2 H 0.5417 0.7324 0.0739 0.054 Uiso 1 1 calc R . . . .
C13 C 0.67513(17) 0.1936(7) 0.3831(2) 0.0381(8) Uani 1 1 d . . . . .
H13 H 0.6982 0.0809 0.3454 0.046 Uiso 1 1 calc R . . . .
C5 C 0.51212(17) 0.9275(8) 0.3346(3) 0.0410(9) Uani 1 1 d . . . . .
H5 H 0.5048 0.9771 0.3994 0.049 Uiso 1 1 calc R . . . .
C17 C 0.70862(17) 0.2109(7) 0.1590(2) 0.0346(8) Uani 1 1 d . . . . .
C18 C 0.7743(2) 0.2817(7) 0.2106(2) 0.0420(9) Uani 1 1 d . . . . .
C12 C 0.68003(17) 0.1716(8) 0.4878(2) 0.0426(9) Uani 1 1 d . . . . .
H12 H 0.7073 0.0432 0.5209 0.051 Uiso 1 1 calc R . . . .
C11 C 0.6448(2) 0.3385(8) 0.5439(2) 0.0480(10) Uani 1 1 d . . . . .
H11 H 0.6493 0.3201 0.6140 0.058 Uiso 1 1 calc R . . . .
C4 C 0.47940(18) 1.0554(8) 0.2506(3) 0.0483(10) Uani 1 1 d . . . . .
H4 H 0.4495 1.1902 0.2585 0.058 Uiso 1 1 calc R . . . .
C3 C 0.49128(18) 0.9820(9) 0.1538(3) 0.0515(10) Uani 1 1 d . . . . .
H3 H 0.4693 1.0707 0.0978 0.062 Uiso 1 1 calc R . . . .
C10 C 0.60377(19) 0.5288(7) 0.4983(2) 0.0435(10) Uani 1 1 d . . . . .
H10 H 0.5802 0.6383 0.5367 0.052 Uiso 1 1 calc R . . . .
C19 C 0.8315(2) 0.1307(8) 0.1894(3) 0.0485(10) Uani 1 1 d . . . . .
H19 H 0.8786 0.1544 0.2185 0.058 Uiso 1 1 calc R . . . .
C20 C 0.80982(18) -0.0515(9) 0.1224(2) 0.0513(10) Uani 1 1 d . . . . .
H20 H 0.8404 -0.1692 0.1002 0.062 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
S16 C17 1.735(4) . ?
S16 C20 1.710(4) . ?
F1 C18 1.314(4) . ?
O15 C14 1.222(3) . ?
N9 C8 1.441(4) . ?
N9 C14 1.395(4) . ?
N9 C1 1.414(5) . ?
C6 C1 1.405(4) . ?
C6 C7 1.448(5) . ?
C6 C5 1.387(5) . ?
C8 C7 1.401(5) . ?
C8 C13 1.386(5) . ?
C14 C17 1.471(5) . ?
C1 C2 1.391(4) . ?
C7 C10 1.409(4) . ?
C2 C3 1.380(5) . ?
C13 C12 1.388(4) . ?
C5 C4 1.380(5) . ?
C17 C18 1.386(4) . ?
C18 C19 1.410(5) . ?
C12 C11 1.390(5) . ?
C11 C10 1.367(5) . ?
C4 C3 1.394(5) . ?
C19 C20 1.344(5) . ?

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
C20 S16 C17 91.88(19) . . ?
C14 N9 C8 128.2(3) . . ?
C14 N9 C1 123.7(2) . . ?
C1 N9 C8 107.8(3) . . ?
C1 C6 C7 106.8(3) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 133.6(3) . . ?
C7 C8 N9 107.3(3) . . ?
C13 C8 N9 130.7(3) . . ?
C13 C8 C7 121.8(3) . . ?
O15 C14 N9 120.6(3) . . ?
O15 C14 C17 120.7(3) . . ?
N9 C14 C17 118.6(3) . . ?
C6 C1 N9 109.2(3) . . ?
C2 C1 N9 129.6(3) . . ?
C2 C1 C6 121.2(3) . . ?
C8 C7 C6 108.9(3) . . ?
C8 C7 C10 119.1(3) . . ?
C10 C7 C6 131.9(3) . . ?
C3 C2 C1 117.7(3) . . ?
C8 C13 C12 117.7(3) . . ?
C4 C5 C6 119.7(3) . . ?
C14 C17 S16 118.5(2) . . ?
C18 C17 S16 109.2(3) . . ?
C18 C17 C14 131.5(4) . . ?
F1 C18 C17 122.5(3) . . ?
F1 C18 C19 123.5(3) . . ?
C17 C18 C19 114.1(4) . . ?
C13 C12 C11 121.0(3) . . ?
C10 C11 C12 121.5(3) . . ?
C5 C4 C3 119.9(4) . . ?
C2 C3 C4 121.9(3) . . ?
C11 C10 C7 118.8(3) . . ?
C20 C19 C18 111.9(3) . . ?
C19 C20 S16 113.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.808
####################################################################### 
# 
# 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_01173clscz_0m
_database_code_depnum_ccdc_archive 'CCDC 2202708'
loop_
_audit_author_name
_audit_author_address
'Wang Zhaoyu'
;Nanjing University of Technology
China
;
_audit_update_record             
;
2022-08-22 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 Cl N O S'
_chemical_formula_sum            'C17 H10 Cl N O S'
_chemical_formula_weight         311.77
_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'
S S 0.1246 0.1234 '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                   12.022(2)
_cell_length_b                   7.1624(10)
_cell_length_c                   16.3850(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.386(6)
_cell_angle_gamma                90
_cell_volume                     1410.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4476
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      26.326
_cell_measurement_theta_min      2.489
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15223
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_min         2.487
_diffrn_ambient_temperature      299.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2079
_reflns_number_total             2889
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    ?
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.021
_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)+(0.0372P)²+0.6376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.1020
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L)
;
_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
S01 S 0.10459(5) 1.04110(8) 0.30512(4) 0.0595(2) Uani 1 1 d . . . . .
Cl02 Cl 0.20982(6) 0.52217(10) 0.21412(4) 0.0700(2) Uani 1 1 d . . . . .
O003 O 0.08968(12) 0.7250(2) 0.43850(10) 0.0556(4) Uani 1 1 d . . . . .
N004 N 0.25697(13) 0.6062(2) 0.40287(11) 0.0425(4) Uani 1 1 d . . . . .
C005 C 0.15569(16) 0.8168(3) 0.31038(14) 0.0414(5) Uani 1 1 d . . . . .
C006 C 0.25387(18) 0.4309(3) 0.44347(13) 0.0437(5) Uani 1 1 d . . . . .
C007 C 0.16397(17) 0.7176(3) 0.38942(14) 0.0421(5) Uani 1 1 d . . . . .
C008 C 0.36622(16) 0.6334(3) 0.37375(13) 0.0427(5) Uani 1 1 d . . . . .
C009 C 0.43063(18) 0.4769(3) 0.39506(14) 0.0471(5) Uani 1 1 d . . . . .
C00A C 0.35879(19) 0.3473(3) 0.43692(13) 0.0480(5) Uani 1 1 d . . . . .
C00B C 0.16670(17) 0.7460(3) 0.23395(14) 0.0467(5) Uani 1 1 d . . . . .
C00C C 0.41164(18) 0.7862(3) 0.33497(15) 0.0522(6) Uani 1 1 d . . . . .
H00C H 0.3689 0.8908 0.3221 0.063 Uiso 1 1 calc R . . . .
C00D C 0.13476(18) 0.8704(4) 0.17069(15) 0.0556(6) Uani 1 1 d . . . . .
H00D H 0.1369 0.8426 0.1153 0.067 Uiso 1 1 calc R . . . .
C00E C 0.1658(2) 0.3418(3) 0.48002(14) 0.0510(6) Uani 1 1 d . . . . .
H00E H 0.0968 0.3991 0.4841 0.061 Uiso 1 1 calc R . . . .
C00F C 0.1850(2) 0.1639(3) 0.51015(15) 0.0624(7) Uani 1 1 d . . . . .
H00F H 0.1276 0.1004 0.5351 0.075 Uiso 1 1 calc R . . . .
C00G C 0.3750(2) 0.1680(4) 0.46769(16) 0.0629(7) Uani 1 1 d . . . . .
H00G H 0.4438 0.1097 0.4638 0.075 Uiso 1 1 calc R . . . .
C00H C 0.5428(2) 0.4728(4) 0.37552(16) 0.0608(7) Uani 1 1 d . . . . .
H00H H 0.5867 0.3697 0.3889 0.073 Uiso 1 1 calc R . . . .
C00I C 0.52343(19) 0.7772(4) 0.31609(16) 0.0607(7) Uani 1 1 d . . . . .
H00I H 0.5559 0.8771 0.2893 0.073 Uiso 1 1 calc R . . . .
C00J C 0.5875(2) 0.6229(4) 0.33628(17) 0.0669(7) Uani 1 1 d . . . . .
H00J H 0.6622 0.6210 0.3230 0.080 Uiso 1 1 calc R . . . .
C00K C 0.1008(2) 1.0347(4) 0.20137(17) 0.0625(7) Uani 1 1 d . . . . .
H00K H 0.0776 1.1347 0.1690 0.075 Uiso 1 1 calc R . . . .
C00L C 0.2878(3) 0.0783(4) 0.50392(17) 0.0696(8) Uani 1 1 d . . . . .
H00L H 0.2980 -0.0417 0.5245 0.083 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
S01 C005 1.721(2) . ?
S01 C00K 1.700(3) . ?
Cl02 C00B 1.718(2) . ?
O003 C007 1.217(2) . ?
N004 C006 1.422(3) . ?
N004 C007 1.387(3) . ?
N004 C008 1.422(3) . ?
C005 C007 1.479(3) . ?
C005 C00B 1.361(3) . ?
C006 C00A 1.403(3) . ?
C006 C00E 1.384(3) . ?
C008 C009 1.402(3) . ?
C008 C00C 1.384(3) . ?
C009 C00A 1.451(3) . ?
C009 C00H 1.394(3) . ?
C00A C00G 1.391(3) . ?
C00B C00D 1.413(3) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.388(3) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.347(4) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.384(3) . ?
C00F H00F 0.9300 . ?
C00F C00L 1.386(4) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.377(4) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.369(4) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.383(4) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L H00L 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
C00K S01 C005 91.47(12) . . ?
C007 N004 C006 123.52(17) . . ?
C007 N004 C008 128.00(18) . . ?
C008 N004 C006 108.23(16) . . ?
C007 C005 S01 120.59(16) . . ?
C00B C005 S01 110.14(17) . . ?
C00B C005 C007 128.4(2) . . ?
C00A C006 N004 107.90(18) . . ?
C00E C006 N004 129.7(2) . . ?
C00E C006 C00A 122.3(2) . . ?
O003 C007 N004 121.4(2) . . ?
O003 C007 C005 121.52(19) . . ?
N004 C007 C005 116.92(18) . . ?
C009 C008 N004 108.44(18) . . ?
C00C C008 N004 129.81(19) . . ?
C00C C008 C009 121.7(2) . . ?
C008 C009 C00A 107.31(18) . . ?
C00H C009 C008 119.4(2) . . ?
C00H C009 C00A 133.2(2) . . ?
C006 C00A C009 108.04(19) . . ?
C00G C00A C006 119.0(2) . . ?
C00G C00A C009 133.0(2) . . ?
C005 C00B Cl02 123.94(18) . . ?
C005 C00B C00D 114.2(2) . . ?
C00D C00B Cl02 121.84(19) . . ?
C008 C00C H00C 121.3 . . ?
C008 C00C C00I 117.4(2) . . ?
C00I C00C H00C 121.3 . . ?
C00B C00D H00D 124.6 . . ?
C00K C00D C00B 110.9(2) . . ?
C00K C00D H00D 124.6 . . ?
C006 C00E H00E 121.4 . . ?
C00F C00E C006 117.1(2) . . ?
C00F C00E H00E 121.4 . . ?
C00E C00F H00F 119.2 . . ?
C00E C00F C00L 121.5(2) . . ?
C00L C00F H00F 119.2 . . ?
C00A C00G H00G 120.5 . . ?
C00L C00G C00A 119.1(2) . . ?
C00L C00G H00G 120.5 . . ?
C009 C00H H00H 120.5 . . ?
C00J C00H C009 118.9(2) . . ?
C00J C00H H00H 120.5 . . ?
C00C C00I H00I 119.3 . . ?
C00J C00I C00C 121.3(2) . . ?
C00J C00I H00I 119.3 . . ?
C00H C00J C00I 121.2(2) . . ?
C00H C00J H00J 119.4 . . ?
C00I C00J H00J 119.4 . . ?
S01 C00K H00K 123.3 . . ?
C00D C00K S01 113.3(2) . . ?
C00D C00K H00K 123.3 . . ?
C00F C00L H00L 119.5 . . ?
C00G C00L C00F 121.0(2) . . ?
C00G C00L H00L 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
