# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_exp_6002
_audit_block_doi                 10.5517/ccdc.csd.cc20ynf2
_database_code_depnum_ccdc_archive 'CCDC 1875544'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Huaqiao University
China
;
_audit_update_record             
;
2018-10-26 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_audit_creation_date             2018-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H5 F2 N O S'
_chemical_formula_sum            'C8 H5 F2 N O S'
_chemical_formula_weight         201.19
_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'
F F 0.0171 0.0103 '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                   6.9739(6)
_cell_length_b                   16.0078(17)
_cell_length_c                   7.5851(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.787(9)
_cell_angle_gamma                90
_cell_volume                     836.84(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1331
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8950
_cell_measurement_theta_min      3.9140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_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  0.0413
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3212
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         3.724
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  73.00   1.00    1.00    --   15.65   0.00  60.00  118
  2  ω     10.00  53.00   1.00    1.00    --   15.65 -99.00 -90.00   43
  3  ω     -6.00  21.00   1.00    1.00    --  -16.59 -99.00 -30.00   27
  4  ω    -21.00   8.00   1.00    1.00    --  -16.59 -99.00 -60.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0193384000
_diffrn_orient_matrix_UB_12      -0.0101978000
_diffrn_orient_matrix_UB_13      -0.0919699000
_diffrn_orient_matrix_UB_21      -0.0056812000
_diffrn_orient_matrix_UB_22      0.0431357000
_diffrn_orient_matrix_UB_23      -0.0217373000
_diffrn_orient_matrix_UB_31      0.1009078000
_diffrn_orient_matrix_UB_32      0.0005033000
_diffrn_orient_matrix_UB_33      -0.0041401000
_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              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1154
_reflns_number_total             1461
_reflns_odcompleteness_completeness 99.44
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.568
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.248
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.396
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0894
_refine_ls_restrained_S_all      1.396
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2188
_refine_special_details          ?
_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:
 N003(H003), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C)
;
_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
S001 S 0.45394(15) 0.34901(8) 0.23571(14) 0.0559(5) Uani 1 1 d . . . . .
O002 O -0.0375(3) 0.4505(2) 0.2858(4) 0.0583(9) Uani 1 1 d . . . . .
N003 N 0.2237(4) 0.4349(2) 0.4995(4) 0.0411(8) Uani 1 1 d . . . . .
H003 H 0.171512 0.468935 0.566097 0.049 Uiso 1 1 calc R . . . .
F004 F 0.1395(5) 0.2757(2) 0.2948(6) 0.1196(16) Uani 1 1 d . . . . .
F005 F 0.1169(5) 0.3575(3) 0.0637(5) 0.1315(19) Uani 1 1 d . . . . .
C006 C 0.4098(5) 0.4047(2) 0.5722(5) 0.0346(9) Uani 1 1 d . . . . .
C007 C 0.5268(5) 0.3638(2) 0.4657(5) 0.0378(9) Uani 1 1 d . . . . .
C008 C 0.1188(5) 0.4179(2) 0.3425(5) 0.0421(10) Uani 1 1 d . . . . .
C009 C 0.4800(5) 0.4205(3) 0.7490(6) 0.0479(10) Uani 1 1 d . . . . .
H009 H 0.402095 0.447603 0.820219 0.057 Uiso 1 1 calc R . . . .
C00A C 0.6654(6) 0.3961(3) 0.8207(6) 0.0532(11) Uani 1 1 d . . . . .
H00A H 0.712638 0.406997 0.939837 0.064 Uiso 1 1 calc R . . . .
C00B C 0.7111(5) 0.3379(3) 0.5418(6) 0.0483(11) Uani 1 1 d . . . . .
H00B H 0.787414 0.308105 0.473351 0.058 Uiso 1 1 calc R . . . .
C00C C 0.7812(6) 0.3554(3) 0.7147(6) 0.0516(11) Uani 1 1 d . . . . .
H00C H 0.907121 0.339981 0.762215 0.062 Uiso 1 1 calc R . . . .
C00D C 0.2006(6) 0.3503(3) 0.2340(6) 0.0574(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C007 1.757(4) . ?
S001 C00D 1.765(4) . ?
O002 C008 1.226(4) . ?
N003 H003 0.8600 . ?
N003 C006 1.416(4) . ?
N003 C008 1.327(5) . ?
F004 C00D 1.371(6) . ?
F005 C00D 1.339(5) . ?
C006 C007 1.396(5) . ?
C006 C009 1.379(5) . ?
C007 C00B 1.389(6) . ?
C008 C00D 1.522(6) . ?
C009 H009 0.9300 . ?
C009 C00A 1.381(5) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.386(6) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.357(6) . ?
C00C H00C 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
C007 S001 C00D 98.21(18) . . ?
C006 N003 H003 115.6 . . ?
C008 N003 H003 115.6 . . ?
C008 N003 C006 128.8(3) . . ?
C007 C006 N003 121.1(3) . . ?
C009 C006 N003 119.0(3) . . ?
C009 C006 C007 119.8(3) . . ?
C006 C007 S001 122.1(3) . . ?
C00B C007 S001 118.8(3) . . ?
C00B C007 C006 119.0(4) . . ?
O002 C008 N003 124.5(4) . . ?
O002 C008 C00D 120.0(4) . . ?
N003 C008 C00D 115.5(3) . . ?
C006 C009 H009 119.9 . . ?
C006 C009 C00A 120.2(4) . . ?
C00A C009 H009 119.9 . . ?
C009 C00A H00A 120.1 . . ?
C009 C00A C00C 119.9(4) . . ?
C00C C00A H00A 120.1 . . ?
C007 C00B H00B 119.5 . . ?
C00C C00B C007 120.9(4) . . ?
C00C C00B H00B 119.5 . . ?
C00A C00C H00C 119.9 . . ?
C00B C00C C00A 120.1(3) . . ?
C00B C00C H00C 119.9 . . ?
F004 C00D S001 110.4(3) . . ?
F004 C00D C008 106.0(4) . . ?
F005 C00D S001 107.3(3) . . ?
F005 C00D F004 106.7(4) . . ?
F005 C00D C008 108.4(4) . . ?
C008 C00D S001 117.5(3) . . ?

_olex2_date_sample_data_collection 2018-10-24
_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 1.453
_oxdiff_exptl_absorpt_empirical_full_min 0.792
####################################################################### 
# 
# 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_exp_6200
_database_code_depnum_ccdc_archive 'CCDC 1883275'
loop_
_audit_author_name
_audit_author_address
'Shuilin Deng'
;Huaqiao University
China
;
_audit_update_record             
;
2018-12-05 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_audit_creation_date             2018-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C16 H14 N2 O3'
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.30
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      2
_cell_length_a                   6.3315(8)
_cell_length_b                   6.8983(9)
_cell_length_c                   16.780(2)
_cell_angle_alpha                97.492(10)
_cell_angle_beta                 98.979(10)
_cell_angle_gamma                100.301(11)
_cell_volume                     702.72(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1203
_cell_measurement_theta_max      25.7340
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_cell_measurement_theta_min      4.2400
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3341
_exptl_crystal_F_000             296.1544
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5605
_diffrn_reflns_theta_full        24.9949
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.61
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0744485000
_diffrn_orient_matrix_UB_12      -0.0387982000
_diffrn_orient_matrix_UB_13      -0.0372105000
_diffrn_orient_matrix_UB_21      -0.0806046000
_diffrn_orient_matrix_UB_22      -0.0371771000
_diffrn_orient_matrix_UB_23      0.0222420000
_diffrn_orient_matrix_UB_31      -0.0371343000
_diffrn_orient_matrix_UB_32      0.0912803000
_diffrn_orient_matrix_UB_33      0.0014408000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                1783
_reflns_number_total             2474
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.2093
_refine_diff_density_min         -0.2883
_refine_diff_density_rms         0.0669
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             5.6516
_refine_ls_goodness_of_fit_ref   0.9286
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      0.9284
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1539
_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. Rigid bond restraints
 N002, C009
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C00G(H00a,H00c)
3.b Aromatic/amide H refined with riding coordinates:
 N005(H005), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K)
3.c Idealised Me refined as rotating group:
 C00L(H00g,H00l,H00m)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
O001 O 1.1774(2) 0.77284(19) 0.42563(8) 0.0531(4) Uani 1.000000 . .
N002 N 0.8572(2) 0.7376(2) 0.46876(9) 0.0431(4) Uani 1.000000 . U
O003 O 0.9627(3) 0.7662(2) 0.26848(9) 0.0724(5) Uani 1.000000 . .
O004 O 0.2460(3) -0.0746(2) 0.06589(9) 0.0788(5) Uani 1.000000 . .
N005 N 0.6383(3) 0.7319(2) 0.31102(10) 0.0514(5) Uani 1.000000 . .
H005 H 0.5757(3) 0.7240(2) 0.35276(10) 0.0617(6) Uiso 1.000000 R .
C006 C 1.0237(3) 0.7475(2) 0.53589(12) 0.0409(5) Uani 1.000000 . .
C007 C 1.2198(3) 0.7702(3) 0.50907(11) 0.0442(5) Uani 1.000000 . .
C008 C 0.4270(3) 0.5123(3) 0.18538(12) 0.0514(5) Uani 1.000000 . .
C009 C 0.9572(3) 0.7525(3) 0.40803(12) 0.0449(5) Uani 1.000000 . U
C00A C 0.8536(4) 0.7511(3) 0.32208(12) 0.0489(5) Uani 1.000000 . .
C00B C 1.0176(3) 0.7393(3) 0.61771(12) 0.0518(5) Uani 1.000000 . .
H00B H 0.8865(3) 0.7240(3) 0.63692(12) 0.0621(6) Uiso 1.000000 R .
C00C C 0.2953(4) 0.1169(3) 0.10695(12) 0.0560(6) Uani 1.000000 . .
C00D C 0.1670(4) 0.1990(3) 0.15534(12) 0.0588(6) Uani 1.000000 . .
H00D H 0.0364(4) 0.1229(3) 0.16240(12) 0.0705(7) Uiso 1.000000 R .
C00E C 1.2124(4) 0.7546(3) 0.66886(13) 0.0550(6) Uani 1.000000 . .
H00E H 1.2135(4) 0.7482(3) 0.72394(13) 0.0660(7) Uiso 1.000000 R .
C00F C 1.4170(3) 0.7872(3) 0.55961(13) 0.0576(6) Uani 1.000000 . .
H00F H 1.5481(3) 0.8032(3) 0.54043(13) 0.0691(7) Uiso 1.000000 R .
C00G C 0.5027(4) 0.7236(3) 0.23148(13) 0.0594(6) Uani 1.000000 . .
H00a H 0.3762(4) 0.7801(3) 0.23916(13) 0.0713(7) Uiso 1.000000 R .
H00c H 0.5852(4) 0.8043(3) 0.19912(13) 0.0713(7) Uiso 1.000000 R .
C00H C 1.4078(4) 0.7792(3) 0.64070(14) 0.0592(6) Uani 1.000000 . .
H00H H 1.5371(4) 0.7908(3) 0.67758(14) 0.0711(7) Uiso 1.000000 R .
C00I C 0.2337(4) 0.3958(3) 0.19344(12) 0.0566(6) Uani 1.000000 . .
H00I H 0.1451(4) 0.4510(3) 0.22545(12) 0.0679(7) Uiso 1.000000 R .
C00J C 0.5523(4) 0.4267(3) 0.13577(14) 0.0665(6) Uani 1.000000 . .
H00J H 0.6826(4) 0.5028(3) 0.12838(14) 0.0798(8) Uiso 1.000000 R .
C00K C 0.4885(4) 0.2317(4) 0.09721(14) 0.0703(7) Uani 1.000000 . .
H00K H 0.5758(4) 0.1771(4) 0.06445(14) 0.0844(8) Uiso 1.000000 R .
C00L C 0.0475(5) -0.2007(4) 0.07282(15) 0.0818(8) Uani 1.000000 . .
H00g H 0.0310(15) -0.3280(10) 0.0390(9) 0.1227(12) Uiso 1.000000 GR .
H00l H 0.0513(13) -0.219(2) 0.1287(2) 0.1227(12) Uiso 1.000000 GR .
H00m H -0.0733(5) -0.1403(13) 0.0553(10) 0.1227(12) Uiso 1.000000 GR .


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
O001 C007 1.387(2) . ?
O001 C009 1.357(2) . ?
N002 C006 1.403(2) . ?
N002 C009 1.286(2) . ?
O003 C00A 1.221(2) . ?
O004 C00C 1.365(2) . ?
O004 C00L 1.425(3) . ?
N005 H005 0.8600 . ?
N005 C00A 1.327(3) . ?
N005 C00G 1.458(3) . ?
C006 C007 1.375(3) . ?
C006 C00B 1.388(3) . ?
C007 C00F 1.372(3) . ?
C008 C00G 1.514(3) . ?
C008 C00I 1.375(3) . ?
C008 C00J 1.385(3) . ?
C009 C00A 1.486(3) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.367(3) . ?
C00C C00D 1.375(3) . ?
C00C C00K 1.378(3) . ?
C00D H00D 0.9300 . ?
C00D C00I 1.384(3) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.383(3) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.379(3) . ?
C00G H00a 0.9700 . ?
C00G H00c 0.9700 . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00K 1.374(3) . ?
C00K H00K 0.9300 . ?
C00L H00g 0.9600 . ?
C00L H00l 0.9600 . ?
C00L H00m 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 O001 C007 103.55(14) . . ?
C009 N002 C006 104.46(15) . . ?
C00L O004 C00C 118.51(19) . . ?
C00A N005 H005 118.42(11) . . ?
C00G N005 H005 118.42(12) . . ?
C00G N005 C00A 123.15(17) . . ?
C007 C006 N002 108.26(16) . . ?
C00B C006 N002 131.48(18) . . ?
C00B C006 C007 120.26(19) . . ?
C006 C007 O001 107.87(17) . . ?
C00F C007 O001 128.74(17) . . ?
C00F C007 C006 123.39(19) . . ?
C00I C008 C00G 121.01(19) . . ?
C00J C008 C00G 121.5(2) . . ?
C00J C008 C00I 117.43(19) . . ?
N002 C009 O001 115.86(17) . . ?
C00A C009 O001 118.16(16) . . ?
C00A C009 N002 125.97(18) . . ?
N005 C00A O003 125.1(2) . . ?
C009 C00A O003 121.1(2) . . ?
C009 C00A N005 113.75(17) . . ?
H00B C00B C006 121.42(12) . . ?
C00E C00B C006 117.16(19) . . ?
C00E C00B H00B 121.42(12) . . ?
C00D C00C O004 124.8(2) . . ?
C00K C00C O004 115.70(19) . . ?
C00K C00C C00D 119.5(2) . . ?
H00D C00D C00C 120.26(13) . . ?
C00I C00D C00C 119.5(2) . . ?
C00I C00D H00D 120.26(12) . . ?
H00E C00E C00B 119.20(12) . . ?
C00H C00E C00B 121.6(2) . . ?
C00H C00E H00E 119.20(13) . . ?
H00F C00F C007 122.22(12) . . ?
C00H C00F C007 115.57(19) . . ?
C00H C00F H00F 122.22(13) . . ?
C008 C00G N005 112.23(16) . . ?
H00a C00G N005 109.16(11) . . ?
H00a C00G C008 109.16(12) . . ?
H00c C00G N005 109.16(11) . . ?
H00c C00G C008 109.16(11) . . ?
H00c C00G H00a 107.9 . . ?
C00F C00H C00E 122.0(2) . . ?
H00H C00H C00E 118.99(13) . . ?
H00H C00H C00F 118.99(13) . . ?
C00D C00I C008 121.97(19) . . ?
H00I C00I C008 119.02(12) . . ?
H00I C00I C00D 119.02(12) . . ?
H00J C00J C008 119.28(13) . . ?
C00K C00J C008 121.4(2) . . ?
C00K C00J H00J 119.28(13) . . ?
C00J C00K C00C 120.2(2) . . ?
H00K C00K C00C 119.92(13) . . ?
H00K C00K C00J 119.92(13) . . ?
H00g C00L O004 109.5 . . ?
H00l C00L O004 109.5 . . ?
H00l C00L H00g 109.5 . . ?
H00m C00L O004 109.5 . . ?
H00m C00L H00g 109.5 . . ?
H00m C00L H00l 109.5 . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.147
_oxdiff_exptl_absorpt_empirical_full_min 0.640
loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
N002 C009 0.0010 0.0485 -0.0034
####################################################################### 
# 
# 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_exp_6199
_database_code_depnum_ccdc_archive 'CCDC 1883277'
loop_
_audit_author_name
_audit_author_address
'ShuiLin Deng'
;Huaqiao University
China
;
_audit_update_record             
;
2018-12-05 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_audit_creation_date             2018-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C16 H14 N2 O S'
_chemical_formula_sum            'C16 H14 N2 O S'
_chemical_formula_weight         282.37
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      14
_cell_length_a                   8.4561(8)
_cell_length_b                   18.2584(11)
_cell_length_c                   9.6555(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.111(7)
_cell_angle_gamma                90
_cell_volume                     1472.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1732
_cell_measurement_theta_max      26.4740
_cell_measurement_theta_min      4.1340
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2741
_exptl_crystal_F_000             592.7175
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7286
_diffrn_reflns_theta_full        24.9999
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.66
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0245961000
_diffrn_orient_matrix_UB_12      0.0371907000
_diffrn_orient_matrix_UB_13      0.0025772000
_diffrn_orient_matrix_UB_21      -0.0806026000
_diffrn_orient_matrix_UB_22      0.0112570000
_diffrn_orient_matrix_UB_23      -0.0027100000
_diffrn_orient_matrix_UB_31      0.0096383000
_diffrn_orient_matrix_UB_32      -0.0009441000
_diffrn_orient_matrix_UB_33      0.0743781000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1874
_reflns_number_total             2586
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.2599
_refine_diff_density_min         -0.4364
_refine_diff_density_rms         0.0591
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.5620
_refine_ls_goodness_of_fit_ref   0.9981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      0.9981
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1584
_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:
 C009(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00F(H00F), C00E(H00E), C00C(H00d), C00G(H00G), C00J(H00J),
 C00I(H00I), C00A(H00c), N003(H003)
2.c Idealised Me refined as rotating group:
 C00K(H00k,H00l,H00m)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
S01 S 0.68143(9) 0.55632(4) 0.66540(6) 0.0630(3) Uani 1.000000 .
O002 O 0.5462(2) 0.70046(9) 0.73011(16) 0.0561(5) Uani 1.000000 .
N003 N 0.5458(2) 0.75191(9) 0.51577(18) 0.0448(5) Uani 1.000000 .
N004 N 0.6451(2) 0.61777(10) 0.4216(2) 0.0488(5) Uani 1.000000 .
C005 C 0.5670(3) 0.69732(11) 0.6067(2) 0.0422(6) Uani 1.000000 .
C006 C 0.6270(3) 0.62776(11) 0.5510(2) 0.0406(5) Uani 1.000000 .
C007 C 0.3109(3) 0.83216(11) 0.5317(2) 0.0457(6) Uani 1.000000 .
C008 C 0.7074(3) 0.54855(12) 0.4052(2) 0.0459(6) Uani 1.000000 .
C009 C 0.4904(3) 0.82376(12) 0.5526(3) 0.0503(6) Uani 1.000000 .
C00A C 0.2100(3) 0.78678(12) 0.4445(3) 0.0520(6) Uani 1.000000 .
C00B C 0.7354(3) 0.50669(12) 0.5278(3) 0.0508(6) Uani 1.000000 .
C00C C 0.7423(4) 0.51966(14) 0.2801(3) 0.0665(8) Uani 1.000000 .
C00D C 0.0456(3) 0.79653(15) 0.4197(3) 0.0651(8) Uani 1.000000 .
C00E C 0.8034(4) 0.44984(15) 0.2804(3) 0.0716(8) Uani 1.000000 .
C00F C 0.8291(4) 0.40864(14) 0.4017(3) 0.0727(8) Uani 1.000000 .
C00G C 0.2450(4) 0.88937(15) 0.5969(3) 0.0724(8) Uani 1.000000 .
C00H C 0.7957(4) 0.43596(14) 0.5252(3) 0.0736(9) Uani 1.000000 .
C00I C -0.0178(4) 0.8545(2) 0.4856(4) 0.0843(10) Uani 1.000000 .
C00J C 0.0809(5) 0.9006(2) 0.5718(4) 0.0961(12) Uani 1.000000 .
C00K C -0.0588(4) 0.7467(2) 0.3224(5) 0.1102(13) Uani 1.000000 .
H00H H 0.8130(4) 0.40775(14) 0.6064(3) 0.0883(10) Uiso 1.000000 R
H00F H 0.8700(4) 0.36144(14) 0.3991(3) 0.0873(10) Uiso 1.000000 R
H00E H 0.8277(4) 0.43009(15) 0.1975(3) 0.0859(10) Uiso 1.000000 R
H00d H 0.7247(4) 0.54706(14) 0.1979(3) 0.0798(9) Uiso 1.000000 R
H00G H 0.3106(4) 0.92025(15) 0.6575(3) 0.0869(10) Uiso 1.000000 R
H00J H 0.0372(5) 0.9399(2) 0.6139(4) 0.1154(14) Uiso 1.000000 R
H00I H -0.1279(4) 0.8622(2) 0.4712(4) 0.1012(12) Uiso 1.000000 R
H00c H 0.2539(3) 0.74813(12) 0.4007(3) 0.0625(8) Uiso 1.000000 R
H003 H 0.5654(2) 0.74476(9) 0.43209(18) 0.0538(6) Uiso 1.000000 R
H00a H 0.5326(3) 0.83349(12) 0.6503(3) 0.0603(7) Uiso 1.000000 R
H00b H 0.5341(3) 0.86042(12) 0.4966(3) 0.0603(7) Uiso 1.000000 R
H00k H -0.018(2) 0.7435(12) 0.2351(11) 0.165(2) Uiso 1.000000 GR
H00l H -0.059(3) 0.6989(5) 0.3636(14) 0.165(2) Uiso 1.000000 GR
H00m H -0.1660(9) 0.7657(9) 0.306(2) 0.165(2) Uiso 1.000000 GR


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 C006 1.724(2) . ?
S01 C00B 1.729(2) . ?
O002 C005 1.234(2) . ?
N003 C005 1.321(3) . ?
N003 C009 1.456(3) . ?
N003 H003 0.8600 . ?
N004 C006 1.296(3) . ?
N004 C008 1.388(3) . ?
C005 C006 1.498(3) . ?
C007 C009 1.507(3) . ?
C007 C00A 1.377(3) . ?
C007 C00G 1.382(3) . ?
C008 C00B 1.397(3) . ?
C008 C00C 1.391(3) . ?
C009 H00a 0.9700 . ?
C009 H00b 0.9700 . ?
C00A C00D 1.384(4) . ?
C00A H00c 0.9300 . ?
C00B C00H 1.390(3) . ?
C00C C00E 1.375(4) . ?
C00C H00d 0.9300 . ?
C00D C00I 1.386(4) . ?
C00D C00K 1.493(5) . ?
C00E C00F 1.380(4) . ?
C00E H00E 0.9300 . ?
C00F C00H 1.363(4) . ?
C00F H00F 0.9300 . ?
C00G C00J 1.386(5) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I C00J 1.370(5) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K H00k 0.9600 . ?
C00K H00l 0.9600 . ?
C00K H00m 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00B S01 C006 88.88(11) . . ?
C009 N003 C005 122.16(19) . . ?
H003 N003 C005 118.92(12) . . ?
H003 N003 C009 118.92(12) . . ?
C008 N004 C006 110.08(18) . . ?
N003 C005 O002 125.6(2) . . ?
C006 C005 O002 119.6(2) . . ?
C006 C005 N003 114.78(19) . . ?
N004 C006 S01 116.81(16) . . ?
C005 C006 S01 118.87(16) . . ?
C005 C006 N004 124.30(19) . . ?
C00A C007 C009 122.3(2) . . ?
C00G C007 C009 119.1(2) . . ?
C00G C007 C00A 118.5(2) . . ?
C00B C008 N004 114.7(2) . . ?
C00C C008 N004 125.5(2) . . ?
C00C C008 C00B 119.8(2) . . ?
C007 C009 N003 114.54(19) . . ?
H00a C009 N003 108.63(12) . . ?
H00a C009 C007 108.63(12) . . ?
H00b C009 N003 108.63(12) . . ?
H00b C009 C007 108.63(12) . . ?
H00b C009 H00a 107.6 . . ?
C00D C00A C007 122.5(2) . . ?
H00c C00A C007 118.77(14) . . ?
H00c C00A C00D 118.77(16) . . ?
C008 C00B S01 109.54(17) . . ?
C00H C00B S01 130.0(2) . . ?
C00H C00B C008 120.4(2) . . ?
C00E C00C C008 118.7(3) . . ?
H00d C00C C008 120.63(14) . . ?
H00d C00C C00E 120.63(17) . . ?
C00I C00D C00A 118.0(3) . . ?
C00K C00D C00A 120.5(3) . . ?
C00K C00D C00I 121.4(3) . . ?
C00F C00E C00C 121.0(3) . . ?
H00E C00E C00C 119.48(17) . . ?
H00E C00E C00F 119.48(16) . . ?
C00H C00F C00E 121.1(2) . . ?
H00F C00F C00E 119.46(16) . . ?
H00F C00F C00H 119.46(16) . . ?
C00J C00G C007 119.8(3) . . ?
H00G C00G C007 120.11(18) . . ?
H00G C00G C00J 120.1(2) . . ?
C00F C00H C00B 118.9(3) . . ?
H00H C00H C00B 120.57(16) . . ?
H00H C00H C00F 120.57(16) . . ?
C00J C00I C00D 120.3(3) . . ?
H00I C00I C00D 119.8(2) . . ?
H00I C00I C00J 119.84(19) . . ?
C00I C00J C00G 120.8(3) . . ?
H00J C00J C00G 119.6(2) . . ?
H00J C00J C00I 119.58(19) . . ?
H00k C00K C00D 109.5 . . ?
H00l C00K C00D 109.5 . . ?
H00l C00K H00k 109.5 . . ?
H00m C00K C00D 109.5 . . ?
H00m C00K H00k 109.5 . . ?
H00m C00K H00l 109.5 . . ?

_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.731
