# Electronic Supplementary Material (ESI) for ChemComm.
# 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_4927
_audit_block_doi                 10.5517/ccdc.csd.cc1zv421
_database_code_depnum_ccdc_archive 'CCDC 1842363'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Huaqiao University
China
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2019-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_formula_moiety         'C14 H11 N O S'
_chemical_formula_sum            'C14 H11 N O S'
_chemical_formula_weight         241.32
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                   9.7200(19)
_cell_length_b                   17.845(2)
_cell_length_c                   7.7330(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.22(2)
_cell_angle_gamma                90
_cell_volume                     1258.7(4)
_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.09
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1122
_cell_measurement_theta_max      24.5020
_cell_measurement_theta_min      4.4130
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38177
_exptl_absorpt_correction_type   multi-scan
_cell_measurement_temperature    297
_diffrn_ambient_temperature      297
_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    1.2733
_exptl_crystal_F_000             504.6922
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5777
_diffrn_reflns_theta_full        24.9979
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.62
_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_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  45.00   1.00    5.00    --   15.49 -19.00  60.00   68
  2  ω      7.00  84.00   1.00    5.00    --   15.49  38.00-120.00   77
  3  ω     44.00  82.00   1.00    5.00    --   15.49 178.00  90.00   38
  4  ω     49.00  78.00   1.00    5.00    --   15.49 178.00   0.00   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      0.0608102000
_diffrn_orient_matrix_UB_12      0.0157782000
_diffrn_orient_matrix_UB_13      -0.0175330000
_diffrn_orient_matrix_UB_21      0.0482752000
_diffrn_orient_matrix_UB_22      -0.0202666000
_diffrn_orient_matrix_UB_23      0.0755933000
_diffrn_orient_matrix_UB_31      -0.0005120000
_diffrn_orient_matrix_UB_32      -0.0304038000
_diffrn_orient_matrix_UB_33      -0.0593980000
_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              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1416
_reflns_number_total             2210
_reflns_odcompleteness_completeness 99.59
_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., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2038
_refine_diff_density_min         -0.3054
_refine_diff_density_rms         0.0581
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.6298
_refine_ls_goodness_of_fit_ref   0.9020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      0.9020
_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          0.1233
_refine_ls_wR_factor_ref         0.1539
_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.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00D(H00D), C00G(H00G), C008(H008), C00C(H00C), C00F(H00F),
 C00B(H00B), C00A(H00A)
2.b Idealised Me refined as rotating group:
 C00H(H00e,H00h,H00i)
;
_atom_sites_solution_primary     dual
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
S001 S 0.75173(10) 0.49220(4) 0.75323(9) 0.0796(4) Uani 1.000000 .
O002 O 0.6283(2) 0.16770(10) 0.6539(3) 0.0828(6) Uani 1.000000 .
C003 C 0.7913(3) 0.52008(13) 0.5562(3) 0.0532(6) Uani 1.000000 .
C004 C 0.8271(3) 0.59538(13) 0.5442(3) 0.0555(6) Uani 1.000000 .
C005 C 0.6472(3) 0.24334(15) 0.6683(3) 0.0592(7) Uani 1.000000 .
C006 C 0.7118(3) 0.39525(15) 0.7161(3) 0.0591(7) Uani 1.000000 .
C007 C 0.7857(3) 0.47260(14) 0.4124(3) 0.0607(7) Uani 1.000000 .
C008 C 0.8541(3) 0.62163(16) 0.3887(4) 0.0698(8) Uani 1.000000 .
N009 N 0.8436(3) 0.68507(15) 0.8107(4) 0.0996(9) Uani 1.000000 .
C00A C 0.5771(3) 0.37126(16) 0.6004(4) 0.0707(8) Uani 1.000000 .
C00B C 0.5455(3) 0.29571(16) 0.5756(4) 0.0692(7) Uani 1.000000 .
C00C C 0.8137(3) 0.34256(17) 0.8099(4) 0.0694(8) Uani 1.000000 .
C00D C 0.8130(3) 0.49934(16) 0.2607(4) 0.0687(8) Uani 1.000000 .
C00E C 0.8364(3) 0.64544(15) 0.6927(4) 0.0715(8) Uani 1.000000 .
C00F C 0.7815(3) 0.26766(18) 0.7857(4) 0.0725(8) Uani 1.000000 .
C00G C 0.8459(3) 0.57295(18) 0.2473(4) 0.0754(8) Uani 1.000000 .
C00H C 0.4886(4) 0.13996(19) 0.5422(5) 0.0982(11) Uani 1.000000 .
H007 H 0.7634(3) 0.42222(14) 0.4185(3) 0.0729(8) Uiso 1.000000 R
H00D H 0.8089(3) 0.46665(16) 0.1654(4) 0.0824(9) Uiso 1.000000 R
H00G H 0.8628(3) 0.59022(18) 0.1429(4) 0.0905(10) Uiso 1.000000 R
H008 H 0.8774(3) 0.67175(16) 0.3807(4) 0.0838(9) Uiso 1.000000 R
H00C H 0.9049(3) 0.35786(17) 0.8901(4) 0.0832(9) Uiso 1.000000 R
H00F H 0.8515(3) 0.23267(18) 0.8497(4) 0.0870(9) Uiso 1.000000 R
H00B H 0.4544(3) 0.28030(16) 0.4954(4) 0.0830(9) Uiso 1.000000 R
H00A H 0.5065(3) 0.40626(16) 0.5380(4) 0.0848(9) Uiso 1.000000 R
H00e H 0.4670(13) 0.1566(12) 0.4175(8) 0.1473(16) Uiso 1.000000 GR
H00h H 0.4894(9) 0.08618(19) 0.546(3) 0.1473(16) Uiso 1.000000 GR
H00i H 0.4149(5) 0.1584(12) 0.588(2) 0.1473(16) 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
S001 C003 1.767(2) . ?
S001 C006 1.775(3) . ?
O002 C005 1.362(3) . ?
O002 C00H 1.423(4) . ?
C003 C004 1.399(3) . ?
C003 C007 1.384(3) . ?
C004 C008 1.397(3) . ?
C004 C00E 1.433(4) . ?
C005 C00B 1.369(3) . ?
C005 C00F 1.378(4) . ?
C006 C00A 1.374(4) . ?
C006 C00C 1.376(4) . ?
C007 C00D 1.375(3) . ?
C007 H007 0.9300 . ?
C008 C00G 1.377(4) . ?
C008 H008 0.9300 . ?
N009 C00E 1.138(3) . ?
C00A C00B 1.381(4) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00C C00F 1.371(4) . ?
C00C H00C 0.9300 . ?
C00D C00G 1.364(4) . ?
C00D H00D 0.9300 . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H H00e 0.9600 . ?
C00H H00h 0.9600 . ?
C00H H00i 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
C006 S001 C003 103.63(11) . . ?
C00H O002 C005 117.9(2) . . ?
C004 C003 S001 117.47(18) . . ?
C007 C003 S001 124.1(2) . . ?
C007 C003 C004 118.4(2) . . ?
C008 C004 C003 120.3(2) . . ?
C00E C004 C003 119.6(2) . . ?
C00E C004 C008 120.1(2) . . ?
C00B C005 O002 125.5(3) . . ?
C00F C005 O002 115.9(2) . . ?
C00F C005 C00B 118.6(3) . . ?
C00A C006 S001 121.0(2) . . ?
C00C C006 S001 120.2(2) . . ?
C00C C006 C00A 118.7(3) . . ?
C00D C007 C003 120.5(3) . . ?
H007 C007 C003 119.74(15) . . ?
H007 C007 C00D 119.74(16) . . ?
C00G C008 C004 119.7(2) . . ?
H008 C008 C004 120.16(16) . . ?
H008 C008 C00G 120.16(16) . . ?
C00B C00A C006 120.7(2) . . ?
H00A C00A C006 119.65(16) . . ?
H00A C00A C00B 119.65(16) . . ?
C00A C00B C005 120.5(3) . . ?
H00B C00B C005 119.74(17) . . ?
H00B C00B C00A 119.74(16) . . ?
C00F C00C C006 120.4(3) . . ?
H00C C00C C006 119.82(18) . . ?
H00C C00C C00F 119.82(16) . . ?
C00G C00D C007 121.2(3) . . ?
H00D C00D C007 119.39(16) . . ?
H00D C00D C00G 119.39(16) . . ?
N009 C00E C004 179.8(3) . . ?
C00C C00F C005 121.1(3) . . ?
H00F C00F C005 119.44(16) . . ?
H00F C00F C00C 119.44(16) . . ?
C00D C00G C008 119.9(2) . . ?
H00G C00G C008 120.06(16) . . ?
H00G C00G C00D 120.06(16) . . ?
H00e C00H O002 109.5 . . ?
H00h C00H O002 109.5 . . ?
H00h C00H H00e 109.5 . . ?
H00i C00H O002 109.5 . . ?
H00i C00H H00e 109.5 . . ?
H00i C00H H00h 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 3.227
_oxdiff_exptl_absorpt_empirical_full_min 0.583
####################################################################### 
# 
# 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_5832
_audit_block_doi                 10.5517/ccdc.csd.cc20jwyd
_database_code_depnum_ccdc_archive 'CCDC 1863284'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Huaqiao University
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2018-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_formula_moiety         'C14 H9 N O S'
_chemical_formula_sum            'C14 H9 N O S'
_chemical_formula_weight         239.30
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'
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                   7.2127(8)
_cell_length_b                   13.0460(12)
_cell_length_c                   11.9273(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.535(10)
_cell_angle_gamma                90
_cell_volume                     1106.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    986
_cell_measurement_theta_max      26.5530
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.58
_cell_measurement_theta_min      4.2390
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74425
_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    1.4360
_exptl_crystal_F_000             496.6926
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5124
_diffrn_reflns_theta_full        24.9981
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.57
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  82.00   1.00   22.50    --   15.49  38.00 -90.00   85
  2  ω    -17.00  10.00   1.00   22.50    --  -16.12 -99.00-120.00   27
  3  ω    -52.00 -26.00   1.00   22.50    --   15.49 -77.00 120.00   26
  4  ω     16.00  41.00   1.00   22.50    --   15.49 -77.00 120.00   25
  5  ω     35.00  86.00   1.00   22.50    --   15.49 178.00-120.00   51
;
_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      -0.0019455000
_diffrn_orient_matrix_UB_12      -0.0519728000
_diffrn_orient_matrix_UB_13      0.0173787000
_diffrn_orient_matrix_UB_21      -0.0200486000
_diffrn_orient_matrix_UB_22      -0.0154996000
_diffrn_orient_matrix_UB_23      -0.0576776000
_diffrn_orient_matrix_UB_31      0.0976904000
_diffrn_orient_matrix_UB_32      -0.0042613000
_diffrn_orient_matrix_UB_33      -0.0012766000
_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              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1309
_reflns_number_total             1945
_reflns_odcompleteness_completeness 99.58
_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., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3869
_refine_diff_density_min         -0.3713
_refine_diff_density_rms         0.0928
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7045
_refine_ls_goodness_of_fit_ref   0.8443
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      0.8443
_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          0.1214
_refine_ls_wR_factor_ref         0.1443
_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.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00A(H00A), C009(H009), C00B(H00B), C008(H008)
2.b Idealised Me refined as rotating group:
 C00H(H00c,H00f,H00g)
;
_atom_sites_solution_primary     dual
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 0.21822(10) 0.38237(5) 0.40091(7) 0.0499(3) Uani 1.000000 .
O1 O 0.1308(3) 0.82762(15) 0.36941(19) 0.0586(6) Uani 1.000000 .
C003 C 0.2903(3) 0.5014(2) 0.5789(2) 0.0375(7) Uani 1.000000 .
C004 C 0.2306(3) 0.5684(2) 0.4834(2) 0.0382(7) Uani 1.000000 .
C005 C 0.2896(3) 0.3996(2) 0.5453(2) 0.0411(7) Uani 1.000000 .
C006 C 0.3420(4) 0.3214(2) 0.6251(3) 0.0457(8) Uani 1.000000 .
C007 C 0.1531(4) 0.7241(2) 0.3819(3) 0.0445(7) Uani 1.000000 .
C008 C 0.2139(3) 0.6746(2) 0.4829(2) 0.0413(7) Uani 1.000000 .
C009 C 0.1257(4) 0.5642(2) 0.2807(3) 0.0512(8) Uani 1.000000 .
C00A C 0.3451(4) 0.5254(2) 0.6930(3) 0.0456(7) Uani 1.000000 .
C00B C 0.1078(4) 0.6687(2) 0.2818(3) 0.0493(8) Uani 1.000000 .
C00C C 0.1876(3) 0.5139(2) 0.3832(2) 0.0421(7) Uani 1.000000 .
C00D C 0.3953(4) 0.3478(2) 0.7374(3) 0.0509(8) Uani 1.000000 .
C00E C 0.3979(4) 0.4494(2) 0.7713(3) 0.0515(8) Uani 1.000000 .
N00F N 0.3337(5) 0.1343(2) 0.5579(3) 0.0840(10) Uani 1.000000 .
C00G C 0.3377(4) 0.2165(3) 0.5890(3) 0.0575(9) Uani 1.000000 .
C00H C 0.1702(5) 0.8882(2) 0.4681(3) 0.0626(9) Uani 1.000000 .
H00D H 0.4300(4) 0.2968(2) 0.7913(3) 0.0611(9) Uiso 1.000000 R
H00E H 0.4356(4) 0.4661(2) 0.8475(3) 0.0618(10) Uiso 1.000000 R
H00A H 0.3460(4) 0.5934(2) 0.7164(3) 0.0548(9) Uiso 1.000000 R
H009 H 0.0971(4) 0.5277(2) 0.2131(3) 0.0614(9) Uiso 1.000000 R
H00B H 0.0645(4) 0.7031(2) 0.2142(3) 0.0592(9) Uiso 1.000000 R
H008 H 0.2435(3) 0.7117(2) 0.5502(2) 0.0496(8) Uiso 1.000000 R
H00c H 0.150(3) 0.9591(3) 0.4483(4) 0.0938(14) Uiso 1.000000 GR
H00f H 0.089(2) 0.8685(11) 0.5205(8) 0.0938(14) Uiso 1.000000 GR
H00g H 0.2988(10) 0.8784(13) 0.5029(10) 0.0938(14) 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 C005 1.729(3) . ?
S01 C00C 1.738(3) . ?
O1 C007 1.365(3) . ?
O1 C00H 1.408(4) . ?
C003 C004 1.444(4) . ?
C003 C005 1.387(4) . ?
C003 C00A 1.388(4) . ?
C004 C008 1.392(4) . ?
C004 C00C 1.381(4) . ?
C005 C006 1.403(4) . ?
C006 C00D 1.375(4) . ?
C006 C00G 1.433(4) . ?
C007 C008 1.374(4) . ?
C007 C00B 1.388(4) . ?
C008 H008 0.9300 . ?
C009 C00B 1.369(4) . ?
C009 C00C 1.394(4) . ?
C009 H009 0.9300 . ?
C00A C00E 1.372(4) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00D C00E 1.384(4) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
N00F C00G 1.134(4) . ?
C00H H00c 0.9600 . ?
C00H H00f 0.9600 . ?
C00H H00g 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
C00C S01 C005 90.22(13) . . ?
C00H O1 C007 117.4(2) . . ?
C005 C003 C004 111.4(3) . . ?
C00A C003 C004 129.5(3) . . ?
C00A C003 C005 119.1(3) . . ?
C008 C004 C003 128.3(3) . . ?
C00C C004 C003 111.5(3) . . ?
C00C C004 C008 120.2(3) . . ?
C003 C005 S01 113.5(2) . . ?
C006 C005 S01 125.7(2) . . ?
C006 C005 C003 120.8(3) . . ?
C00D C006 C005 118.6(3) . . ?
C00G C006 C005 120.1(3) . . ?
C00G C006 C00D 121.4(3) . . ?
C008 C007 O1 125.1(3) . . ?
C00B C007 O1 114.5(3) . . ?
C00B C007 C008 120.4(3) . . ?
C007 C008 C004 119.1(3) . . ?
H008 C008 C004 120.46(17) . . ?
H008 C008 C007 120.46(17) . . ?
C00C C009 C00B 118.6(3) . . ?
H009 C009 C00B 120.72(18) . . ?
H009 C009 C00C 120.72(18) . . ?
C00E C00A C003 120.4(3) . . ?
H00A C00A C003 119.80(16) . . ?
H00A C00A C00E 119.80(18) . . ?
C009 C00B C007 121.2(3) . . ?
H00B C00B C007 119.42(18) . . ?
H00B C00B C009 119.42(18) . . ?
C004 C00C S01 113.4(2) . . ?
C009 C00C S01 126.0(2) . . ?
C009 C00C C004 120.6(3) . . ?
C00E C00D C006 120.8(3) . . ?
H00D C00D C006 119.58(18) . . ?
H00D C00D C00E 119.58(18) . . ?
C00D C00E C00A 120.2(3) . . ?
H00E C00E C00A 119.88(18) . . ?
H00E C00E C00D 119.88(18) . . ?
N00F C00G C006 178.4(4) . . ?
H00c C00H O1 109.5 . . ?
H00f C00H O1 109.5 . . ?
H00f C00H H00c 109.5 . . ?
H00g C00H O1 109.5 . . ?
H00g C00H H00c 109.5 . . ?
H00g C00H H00f 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 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.724
