# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_T
_database_code_depnum_ccdc_archive 'CCDC 1849437'
_audit_update_record             
;
2018-06-14 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_audit_creation_date             2018-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H11 Cl2 N O2 S'
_chemical_formula_sum            'C12 H11 Cl2 N O2 S'
_chemical_formula_weight         304.20
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
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'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'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'
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'
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'
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'

_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                   11.687(2)
_cell_length_b                   9.6570(19)
_cell_length_c                   11.950(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.80(3)
_cell_angle_gamma                90
_cell_volume                     1339.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3701
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      2.72
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.8839
_exptl_absorpt_correction_T_min  0.8329
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             625.9112
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11542
_diffrn_reflns_theta_full        24.9949
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.72
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9983
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1967
_reflns_number_total             2347
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT A '
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.3371
_refine_diff_density_min         -0.8766
_refine_diff_density_rms         0.1275
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             7.4901
_refine_ls_goodness_of_fit_ref   1.0563
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0954
_refine_ls_restrained_S_all      1.0547
_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)+(0.1651P)²+4.5730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2761
_refine_ls_wR_factor_ref         0.2893
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C5, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C5 \\sim C6: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Others
 Fixed Sof: H1(0) H4(0)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3)
5.d X=CH2 refined with riding coordinates:
 N1(H1a,H1b)
5.e Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c)
;
_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
_atom_site_disorder_group
S S 0.68328(12) 0.25608(14) -0.15497(12) 0.0476(5) Uani 1.000000 . . .
Cl1 Cl 1.20890(19) 0.0791(3) 0.1714(2) 0.1000(9) Uani 1.000000 . . .
Cl2 Cl 0.9935(2) -0.0454(2) 0.26790(17) 0.0925(8) Uani 1.000000 . . .
C1 C 1.0682(6) 0.1253(7) 0.1133(5) 0.0571(16) Uani 1.000000 . . .
C2 C 1.0594(7) 0.2126(8) 0.0257(6) 0.0671(18) Uani 1.000000 . . .
C3 C 0.9524(7) 0.2580(7) -0.0160(6) 0.0642(18) Uani 1.000000 . . .
C4 C 0.8566(5) 0.2183(6) 0.0269(5) 0.0468(13) Uani 1.000000 . . .
C5 C 0.8675(6) 0.1215(7) 0.1158(5) 0.0604(15) Uani 1.000000 . U 1
C6 C 0.9762(6) 0.0713(6) 0.1598(5) 0.0556(15) Uani 1.000000 . U 1
C7 C 0.7366(6) 0.2802(8) -0.0034(5) 0.0598(17) Uani 1.000000 . . .
H7 H 0.6826(6) 0.2374(8) 0.0431(5) 0.072(2) Uiso 1.000000 R . .
C8 C 0.7362(6) 0.4388(7) 0.0129(5) 0.0586(17) Uani 1.000000 . . .
H8a H 0.7228(6) 0.4613(7) 0.0894(5) 0.070(2) Uiso 1.000000 R . .
H8b H 0.8100(6) 0.4773(7) -0.0005(5) 0.070(2) Uiso 1.000000 R . .
C9 C 0.6419(5) 0.4982(6) -0.0694(5) 0.0462(13) Uani 1.000000 . . .
C10 C 0.6071(4) 0.4136(5) -0.1575(4) 0.0409(12) Uani 1.000000 . . .
C11 C 0.5961(5) 0.6337(6) -0.0592(5) 0.0439(12) Uani 1.000000 . . .
C12 C 0.6082(7) 0.8355(7) 0.0556(7) 0.074(2) Uani 1.000000 . . .
N1 N 0.5275(4) 0.4380(5) -0.2452(4) 0.0541(13) Uani 1.000000 . . .
H1a H 0.5148(4) 0.3777(5) -0.2981(4) 0.0650(16) Uiso 1.000000 R . .
H1b H 0.4890(4) 0.5141(5) -0.2486(4) 0.0650(16) Uiso 1.000000 R . .
O1 O 0.5205(4) 0.6871(4) -0.1230(4) 0.0542(11) Uani 1.000000 . . .
O2 O 0.6485(4) 0.6992(5) 0.0333(4) 0.0594(12) Uani 1.000000 . . .
H5 H 0.8020(6) 0.0906(7) 0.1455(5) 0.0724(18) Uiso 1.000000 R . 1
H2 H 1.1245(7) 0.2414(8) -0.0057(6) 0.080(2) Uiso 1.000000 R . .
H3 H 0.9456(7) 0.3191(7) -0.0766(6) 0.077(2) Uiso 1.000000 R . .
H12a H 0.630(5) 0.8986(14) -0.000(3) 0.111(3) Uiso 1.000000 GR . .
H12b H 0.5257(8) 0.8343(15) 0.053(5) 0.111(3) Uiso 1.000000 GR . .
H12c H 0.642(4) 0.865(3) 0.129(2) 0.111(3) 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
S C7 1.859(6) . ?
S C10 1.761(5) . ?
Cl1 C1 1.765(7) . ?
Cl2 C6 1.708(6) . ?
C1 C2 1.338(10) . ?
C1 C6 1.370(10) . ?
C2 C3 1.363(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.341(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.410(9) . ?
C4 C7 1.529(8) . ?
C5 C6 1.403(9) . ?
C5 H5 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.544(10) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C8 C9 1.501(7) . ?
C9 C10 1.357(8) . ?
C9 C11 1.424(8) . ?
C10 N1 1.337(7) . ?
C11 O1 1.212(7) . ?
C11 O2 1.354(7) . ?
C12 O2 1.433(8) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
N1 H1a 0.8600 . ?
N1 H1b 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S C7 91.1(3) . . ?
C2 C1 Cl1 116.6(6) . . ?
C3 C2 C1 118.1(7) . . ?
H2 C2 C1 121.0(4) . . ?
H2 C2 C3 121.0(4) . . ?
C4 C3 C2 122.7(7) . . ?
H3 C3 C2 118.7(4) . . ?
H3 C3 C4 118.7(4) . . ?
C7 C4 C3 125.6(6) . . ?
H5 C5 C6 119.7(4) . . ?
C1 C6 Cl2 122.0(5) . . ?
C4 C7 S 111.9(4) . . ?
H7 C7 S 109.6(2) . . ?
H7 C7 C4 109.6(4) . . ?
C8 C7 S 104.0(4) . . ?
C8 C7 C4 112.0(6) . . ?
C8 C7 H7 109.6(4) . . ?
H8a C8 C7 110.1(4) . . ?
H8b C8 C7 110.1(4) . . ?
H8b C8 H8a 108.4 . . ?
C9 C8 C7 108.0(5) . . ?
C9 C8 H8a 110.1(3) . . ?
C9 C8 H8b 110.1(4) . . ?
C10 C9 C8 114.1(5) . . ?
C11 C9 C8 123.3(5) . . ?
C11 C9 C10 122.6(5) . . ?
C9 C10 S 113.7(4) . . ?
N1 C10 S 118.0(4) . . ?
N1 C10 C9 128.2(5) . . ?
O1 C11 C9 126.2(5) . . ?
O2 C11 C9 111.1(5) . . ?
O2 C11 O1 122.7(5) . . ?
H12a C12 O2 109.5 . . ?
H12b C12 O2 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 O2 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H1a N1 C10 120.0 . . ?
H1b N1 C10 120.0 . . ?
H1b N1 H1a 120.0 . . ?
C12 O2 C11 117.0(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
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
C5 C6 0.0010 0.0650 0.0009

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
C5 C6 0.0200

####################################################################### 
# 
# 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_syb-yuanliao-r
_database_code_depnum_ccdc_archive 'CCDC 1852130'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 O4'
_chemical_formula_weight         234.24
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.91560(10)
_cell_length_b                   9.8147(2)
_cell_length_c                   15.3289(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1190.89(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8800
_cell_measurement_theta_min      5.8340
_cell_measurement_theta_max      71.8760

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33543
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.35
_diffrn_reflns_theta_max         72.84
_reflns_number_total             2353
_reflns_number_gt                2345
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0585P)²+0.2354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0351(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(17)
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.79258(10) 0.60670(9) 0.22711(6) 0.0166(2) Uani 1 1 d . . .
O2 O 0.79217(12) 0.83460(10) 0.21952(7) 0.0208(2) Uani 1 1 d . . .
O3 O 0.59474(12) 0.65243(10) 0.06003(6) 0.0195(2) Uani 1 1 d . . .
O4 O 0.32709(12) 0.62285(13) 0.10492(6) 0.0282(3) Uani 1 1 d . . .
C12 C 0.71845(15) 0.72733(13) 0.21708(8) 0.0119(3) Uani 1 1 d . . .
C2 C 0.47177(16) 0.65616(13) 0.11928(8) 0.0155(3) Uani 1 1 d . . .
C6 C 0.50057(14) 0.64834(13) 0.37162(8) 0.0130(3) Uani 1 1 d . . .
C7 C 0.45343(15) 0.53129(13) 0.41745(8) 0.0157(3) Uani 1 1 d . . .
H7 H 0.3814 0.4684 0.3914 0.019 Uiso 1 1 calc R . .
C3 C 0.53098(15) 0.71108(13) 0.20454(8) 0.0126(3) Uani 1 1 d . . .
C8 C 0.51247(18) 0.50754(13) 0.50117(9) 0.0208(3) Uani 1 1 d . . .
H8 H 0.4787 0.4297 0.5311 0.025 Uiso 1 1 calc R . .
C4 C 0.42263(15) 0.67331(13) 0.28446(8) 0.0142(3) Uani 1 1 d . . .
H4 H 0.3254 0.6151 0.2713 0.017 Uiso 1 1 calc R . .
C5 C 0.41293(15) 0.81337(13) 0.24591(9) 0.0172(3) Uani 1 1 d . . .
H5A H 0.4631 0.8876 0.2787 0.021 Uiso 1 1 calc R . .
H5B H 0.3112 0.8374 0.2141 0.021 Uiso 1 1 calc R . .
C11 C 0.61119(17) 0.73995(14) 0.41184(9) 0.0182(3) Uani 1 1 d . . .
H11 H 0.6446 0.8183 0.3824 0.022 Uiso 1 1 calc R . .
C10 C 0.67141(18) 0.71485(15) 0.49508(10) 0.0240(3) Uani 1 1 d . . .
H10 H 0.7460 0.7761 0.5208 0.029 Uiso 1 1 calc R . .
C13 C 0.97266(15) 0.61106(16) 0.24484(10) 0.0227(3) Uani 1 1 d . . .
H13A H 1.0299 0.6540 0.1970 0.034 Uiso 1 1 calc R . .
H13B H 1.0146 0.5200 0.2520 0.034 Uiso 1 1 calc R . .
H13C H 0.9926 0.6621 0.2973 0.034 Uiso 1 1 calc R . .
C1 C 0.54487(19) 0.60483(18) -0.02579(9) 0.0270(3) Uani 1 1 d . . .
H1A H 0.6391 0.6116 -0.0650 0.040 Uiso 1 1 calc R . .
H1B H 0.4535 0.6598 -0.0471 0.040 Uiso 1 1 calc R . .
H1C H 0.5090 0.5116 -0.0220 0.040 Uiso 1 1 calc R . .
C9 C 0.62177(19) 0.59942(16) 0.54059(9) 0.0239(3) Uani 1 1 d . . .
H9 H 0.6612 0.5838 0.5969 0.029 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
O1 C12 1.3302(16) . ?
O1 C13 1.4518(13) . ?
O2 C12 1.2043(16) . ?
O3 C2 1.3318(16) . ?
O3 C1 1.4508(16) . ?
O4 C2 1.2112(16) . ?
C12 C3 1.5048(16) . ?
C2 C3 1.4893(18) . ?
C6 C7 1.3974(18) . ?
C6 C11 1.3983(18) . ?
C6 C4 1.4918(17) . ?
C7 C8 1.3855(19) . ?
C7 H7 0.9300 . ?
C3 C5 1.5111(17) . ?
C3 C4 1.5408(16) . ?
C8 C9 1.388(2) . ?
C8 H8 0.9300 . ?
C4 C5 1.4982(18) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C11 C10 1.384(2) . ?
C11 H11 0.9300 . ?
C10 C9 1.387(2) . ?
C10 H10 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C13 115.38(10) . . ?
C2 O3 C1 115.36(10) . . ?
O2 C12 O1 124.11(11) . . ?
O2 C12 C3 125.06(12) . . ?
O1 C12 C3 110.82(10) . . ?
O4 C2 O3 124.04(12) . . ?
O4 C2 C3 123.69(12) . . ?
O3 C2 C3 112.23(11) . . ?
C7 C6 C11 118.30(12) . . ?
C7 C6 C4 118.35(11) . . ?
C11 C6 C4 123.24(12) . . ?
C8 C7 C6 120.93(12) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C2 C3 C12 117.44(10) . . ?
C2 C3 C5 114.47(11) . . ?
C12 C3 C5 119.06(11) . . ?
C2 C3 C4 115.82(10) . . ?
C12 C3 C4 118.21(10) . . ?
C5 C3 C4 58.79(8) . . ?
C7 C8 C9 120.28(13) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C6 C4 C5 121.68(11) . . ?
C6 C4 C3 121.43(10) . . ?
C5 C4 C3 59.61(8) . . ?
C6 C4 H4 114.4 . . ?
C5 C4 H4 114.4 . . ?
C3 C4 H4 114.4 . . ?
C4 C5 C3 61.59(8) . . ?
C4 C5 H5A 117.6 . . ?
C3 C5 H5A 117.6 . . ?
C4 C5 H5B 117.6 . . ?
C3 C5 H5B 117.6 . . ?
H5A C5 H5B 114.7 . . ?
C10 C11 C6 120.51(13) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C11 C10 C9 120.75(13) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 C9 C8 119.22(13) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        72.84
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_SYB-CHANWU-1
_database_code_depnum_ccdc_archive 'CCDC 1852128'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_formula_moiety         'C12 H13 N O2 S'
_chemical_formula_sum            'C12 H13 N O2 S'
_chemical_formula_weight         235.29
_chemical_absolute_configuration ad
_chemical_oxdiff_formula         'C1 H1 S1 N1'
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 0.01920 0.00962 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 0.33537 0.55136 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 0.05239 0.03377 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 0.03256 0.01839 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   7.5830(2)
_cell_length_b                   6.1506(1)
_cell_length_c                   25.4866(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.003(2)
_cell_angle_gamma                90
_cell_volume                     1184.17(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8800
_cell_measurement_temperature    294
_cell_measurement_theta_max      71.8760
_cell_measurement_theta_min      5.8340
_exptl_absorpt_coefficient_mu    2.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3198
_exptl_crystal_description       block
_exptl_crystal_F_000             498.7537
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22056
_diffrn_reflns_theta_full        73.0353
_diffrn_reflns_theta_max         73.04
_diffrn_reflns_theta_min         3.48
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9753
_diffrn_measured_fraction_theta_max 0.9753
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.50    --  -36.07  57.00 -90.00   84
  2  ω    -69.00  33.00   1.00    1.50    --  -36.07  89.00  13.00  102
  3  ω    -12.00  69.00   1.00    1.50    --   36.07 -89.00-101.00   81
  4  ω      1.00  75.00   1.00    1.50    --   36.07 -99.00-120.00   74
  5  ω    -33.00  55.00   1.00    1.50    --   36.07 -38.00  30.00   88
  6  ω     17.00 105.00   1.00    1.50    --   36.07  38.00 150.00   88
  7  ω    -31.00  63.00   1.00    1.50    --   36.07 -77.00 -90.00   94
  8  ω    -33.00  55.00   1.00    1.50    --   36.07 -38.00 -30.00   88
  9  ω    -33.00  55.00   1.00    1.50    --   36.07 -38.00 -90.00   88
 10  ω     19.00 103.00   1.00    1.50    --   36.07  57.00-180.00   84
 11  ω      1.00  75.00   1.00    1.50    --   36.07 -99.00   0.00   74
 12  ω     23.00  89.00   1.00    1.50    --   36.07-125.00 -90.00   66
 13  ω      1.00  75.00   1.00    1.50    --   36.07 -99.00 120.00   74
 14  ω    -33.00  55.00   1.00    1.50    --   36.07 -38.00 120.00   88
 15  ω     39.00 131.00   1.00    4.50    --  109.31 -30.00 -60.00   92
 16  ω     42.00 127.00   1.00    4.50    --  109.31 -61.00  30.00   85
 17  ω     92.00 178.00   1.00    4.50    --  109.31  45.00  60.00   86
 18  ω     40.00 109.00   1.00    4.50    --  109.31 -95.00-150.00   69
 19  ω     57.00 151.00   1.00    4.50    --  109.31 178.00 -90.00   94
 20  ω     39.00 116.00   1.00    4.50    --  109.31-111.00 -60.00   77
 21  ω     71.00 178.00   1.00    4.50    --  109.31  15.00-180.00  107
 22  ω     71.00 178.00   1.00    4.50    --  109.31  15.00 120.00  107
 23  ω     39.00 131.00   1.00    4.50    --  109.31 -30.00  90.00   92
 24  ω     57.00 151.00   1.00    4.50    --  109.31 178.00 150.00   94
 25  ω     40.00 109.00   1.00    4.50    --  109.31 -95.00   0.00   69
 26  ω     57.00 151.00   1.00    4.50    --  109.31 178.00-180.00   94
 27  ω    100.00 178.00   1.00    4.50    --  109.31  89.00  13.00   78
 28  ω     41.00 127.00   1.00    4.50    --  109.31 -45.00-120.00   86
 29  ω      9.00 104.00   1.00    1.50    --   36.07  77.00-150.00   95
 30  ω     17.00 105.00   1.00    1.50    --   36.07  38.00  90.00   88
 31  ω      9.00 104.00   1.00    1.50    --   36.07  77.00 -30.00   95
 32  ω     19.00 103.00   1.00    1.50    --   36.07  57.00 120.00   84
 33  ω      9.00 104.00   1.00    1.50    --   36.07  77.00 120.00   95
 34  ω      9.00 104.00   1.00    1.50    --   36.07  77.00  60.00   95
 35  ω      9.00 104.00   1.00    1.50    --   36.07  77.00 -90.00   95
 36  ω    -31.00  53.00   1.00    1.50    --   36.07 -57.00 120.00   84
 37  ω      1.00  75.00   1.00    1.50    --   36.07 -99.00  90.00   74
 38  ω     19.00 103.00   1.00    1.50    --   36.07  57.00  30.00   84
 39  ω     17.00 105.00   1.00    1.50    --   36.07  38.00 -30.00   88
 40  ω      9.00 104.00   1.00    1.50    --   36.07  77.00 150.00   95
 41  ω     19.00 103.00   1.00    1.50    --   36.07  57.00 -30.00   84
 42  ω     19.00 103.00   1.00    1.50    --   36.07  57.00 -90.00   84
 43  ω     88.00 178.00   1.00    4.50    --  109.31  30.00 -60.00   90
 44  ω     83.00 156.00   1.00    4.50    --  109.31  77.00  90.00   73
 45  ω     83.00 177.00   1.00    4.50    --  109.31  77.00-120.00   94
 46  ω     83.00 177.00   1.00    4.50    --  109.31  77.00 -60.00   94
 47  ω     88.00 178.00   1.00    4.50    --  109.31  30.00  30.00   90
 48  ω     88.00 178.00   1.00    4.50    --  109.31  30.00-150.00   90
 49  ω     92.00 178.00   1.00    4.50    --  109.31  45.00-120.00   86
 50  ω     88.00 178.00   1.00    4.50    --  109.31  30.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0698555000
_diffrn_orient_matrix_UB_12      -0.1655654000
_diffrn_orient_matrix_UB_13      0.0385648000
_diffrn_orient_matrix_UB_21      0.0471033000
_diffrn_orient_matrix_UB_22      0.1576343000
_diffrn_orient_matrix_UB_23      0.0460511000
_diffrn_orient_matrix_UB_31      -0.1856888000
_diffrn_orient_matrix_UB_32      0.1023721000
_diffrn_orient_matrix_UB_33      -0.0086331000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.965
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              31
_reflns_limit_l_min              -31
_reflns_number_gt                4218
_reflns_number_total             4627
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.2328
_refine_diff_density_min         -0.2232
_refine_diff_density_rms         0.0498
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.007(18)
_refine_ls_d_res_high            0.8060
_refine_ls_d_res_low             12.6947
_refine_ls_goodness_of_fit_ref   1.0693
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4627
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.0693
_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)+(0.0480P)²+0.1736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1062
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C22(H22), C5(H5), C4(H4), C3(H3), C18(H18), C20(H20),
 C21(H21), C19(H19)
2.d X=CH2 refined with riding coordinates:
 N32(H32a,H32b), N16(H16a,H16b)
2.e Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C30(H30a,H30b,H30c)
;
_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
S7 S 0.45128(10) 0.81219(11) 0.19717(2) 0.04887(17) Uani 1.000000 .
S23 S 0.20382(10) -0.02583(12) 0.31632(3) 0.0572(2) Uani 1.000000 .
O13 O 0.8253(3) 1.3990(3) 0.13974(8) 0.0582(5) Uani 1.000000 .
O31 O 0.6393(3) 0.4644(3) 0.28487(8) 0.0587(5) Uani 1.000000 .
O29 O 0.7925(3) 0.2903(3) 0.35203(8) 0.0585(5) Uani 1.000000 .
O15 O 0.9768(3) 1.1823(4) 0.19861(9) 0.0660(6) Uani 1.000000 .
N32 N 0.2944(3) 0.3158(4) 0.26085(8) 0.0555(6) Uani 1.000000 .
H32a H 0.1864(3) 0.3119(4) 0.24741(8) 0.0666(7) Uiso 1.000000 R
H32b H 0.3653(3) 0.4136(4) 0.25087(8) 0.0666(7) Uiso 1.000000 R
N16 N 0.7853(3) 0.8392(4) 0.23652(9) 0.0581(7) Uani 1.000000 .
H16a H 0.7592(3) 0.7285(4) 0.25494(9) 0.0697(8) Uiso 1.000000 R
H16b H 0.8905(3) 0.8925(4) 0.24005(9) 0.0697(8) Uiso 1.000000 R
C1 C 0.3349(3) 0.8704(4) 0.09167(9) 0.0379(5) Uani 1.000000 .
C28 C 0.6488(3) 0.3173(5) 0.31735(9) 0.0431(5) Uani 1.000000 .
C17 C 0.3168(4) -0.2552(4) 0.40769(10) 0.0439(6) Uani 1.000000 .
C12 C 0.8370(4) 1.2267(5) 0.17215(10) 0.0463(6) Uani 1.000000 .
C26 C 0.5161(3) 0.1586(4) 0.32429(9) 0.0417(6) Uani 1.000000 .
C11 C 0.6624(4) 0.9284(4) 0.20242(9) 0.0414(6) Uani 1.000000 .
C6 C 0.4427(4) 0.7079(4) 0.07550(10) 0.0483(6) Uani 1.000000 .
H6 H 0.5418(4) 0.6662(4) 0.09722(10) 0.0579(8) Uiso 1.000000 R
C8 C 0.3709(3) 0.9920(4) 0.14310(9) 0.0405(5) Uani 1.000000 .
H8 H 0.2594(3) 1.0570(4) 0.15205(9) 0.0486(6) Uiso 1.000000 R
C27 C 0.3522(4) 0.1695(4) 0.29730(9) 0.0428(6) Uani 1.000000 .
C10 C 0.6769(3) 1.1053(4) 0.17112(9) 0.0401(5) Uani 1.000000 .
C2 C 0.1891(4) 0.9292(5) 0.05777(11) 0.0522(7) Uani 1.000000 .
H2 H 0.1143(4) 1.0391(5) 0.06757(11) 0.0626(8) Uiso 1.000000 R
C24 C 0.3769(4) -0.1725(5) 0.35677(10) 0.0485(6) Uani 1.000000 .
H24 H 0.4155(4) -0.2965(5) 0.33652(10) 0.0582(7) Uiso 1.000000 R
C22 C 0.3752(4) -0.4551(5) 0.42703(12) 0.0574(8) Uani 1.000000 .
H22 H 0.4433(4) -0.5420(5) 0.40680(12) 0.0689(9) Uiso 1.000000 R
C25 C 0.5331(4) -0.0118(5) 0.36613(12) 0.0548(7) Uani 1.000000 .
H25a H 0.6444(4) -0.0887(5) 0.36493(12) 0.0658(9) Uiso 1.000000 R
H25b H 0.5315(4) 0.0550(5) 0.40055(12) 0.0658(9) Uiso 1.000000 R
C5 C 0.4058(5) 0.6058(5) 0.02747(11) 0.0576(8) Uani 1.000000 .
H5 H 0.4801(5) 0.4962(5) 0.01726(11) 0.0691(9) Uiso 1.000000 R
C9 C 0.5082(3) 1.1758(4) 0.14078(10) 0.0435(6) Uani 1.000000 .
H9a H 0.5293(3) 1.2053(4) 0.10446(10) 0.0521(7) Uiso 1.000000 R
H9b H 0.4644(3) 1.3077(4) 0.15597(10) 0.0521(7) Uiso 1.000000 R
C4 C 0.2601(4) 0.6653(5) -0.00532(12) 0.0600(8) Uani 1.000000 .
H4 H 0.2347(4) 0.5956(5) -0.03748(12) 0.0720(10) Uiso 1.000000 R
C3 C 0.1536(4) 0.8272(6) 0.00992(12) 0.0633(8) Uani 1.000000 .
H3 H 0.0557(4) 0.8696(6) -0.01224(12) 0.0759(10) Uiso 1.000000 R
C18 C 0.2143(5) -0.1321(6) 0.43855(13) 0.0673(9) Uani 1.000000 .
H18 H 0.1721(5) 0.0027(6) 0.42659(13) 0.0808(11) Uiso 1.000000 R
C20 C 0.2320(4) -0.4055(7) 0.50526(13) 0.0808(13) Uani 1.000000 .
H20 H 0.2018(4) -0.4565(7) 0.53764(13) 0.0969(15) Uiso 1.000000 R
C21 C 0.3345(5) -0.5283(6) 0.47572(13) 0.0742(10) Uani 1.000000 .
H21 H 0.3773(5) -0.6619(6) 0.48830(13) 0.0890(12) Uiso 1.000000 R
C14 C 0.9807(5) 1.5310(5) 0.13781(15) 0.0726(10) Uani 1.000000 .
H14a H 0.9569(12) 1.646(3) 0.1128(8) 0.1089(15) Uiso 1.000000 GR
H14b H 1.013(2) 1.592(4) 0.1720(3) 0.1089(15) Uiso 1.000000 GR
H14c H 1.0762(11) 1.4432(11) 0.1273(11) 0.1089(15) Uiso 1.000000 GR
C30 C 0.9293(4) 0.4522(6) 0.35008(16) 0.0768(11) Uani 1.000000 .
H30a H 0.974(3) 0.450(3) 0.3159(4) 0.1153(16) Uiso 1.000000 GR
H30b H 0.8812(10) 0.5932(9) 0.3565(11) 0.1153(16) Uiso 1.000000 GR
H30c H 1.0239(18) 0.421(3) 0.3765(8) 0.1153(16) Uiso 1.000000 GR
C19 C 0.1736(5) -0.2081(8) 0.48736(13) 0.0890(14) Uani 1.000000 .
H19 H 0.1057(5) -0.1229(8) 0.50803(13) 0.1068(17) Uiso 1.000000 R


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
S7 C11 1.748(3) . ?
S7 C8 1.830(3) . ?
S23 C27 1.743(3) . ?
S23 C24 1.834(3) . ?
O13 C12 1.342(3) . ?
O13 C14 1.435(3) . ?
O31 C28 1.224(3) . ?
O29 C28 1.352(3) . ?
O29 C30 1.442(4) . ?
O15 C12 1.236(3) . ?
N32 H32a 0.8600 . ?
N32 H32b 0.8600 . ?
N32 C27 1.339(3) . ?
N16 H16a 0.8600 . ?
N16 H16b 0.8600 . ?
N16 C11 1.336(3) . ?
C1 C6 1.377(4) . ?
C1 C8 1.513(3) . ?
C1 C2 1.391(4) . ?
C28 C26 1.424(4) . ?
C17 C24 1.501(3) . ?
C17 C22 1.382(4) . ?
C17 C18 1.380(4) . ?
C12 C10 1.424(4) . ?
C26 C27 1.369(3) . ?
C26 C25 1.493(4) . ?
C11 C10 1.359(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.541(3) . ?
C10 C9 1.500(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C24 H24 0.9800 . ?
C24 C25 1.545(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.380(4) . ?
C25 H25a 0.9700 . ?
C25 H25b 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.376(4) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C4 H4 0.9300 . ?
C4 C3 1.360(5) . ?
C3 H3 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.389(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.358(5) . ?
C20 C19 1.358(6) . ?
C21 H21 0.9300 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C30 H30a 0.9600 . ?
C30 H30b 0.9600 . ?
C30 H30c 0.9600 . ?
C19 H19 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
C8 S7 C11 93.05(12) . . ?
C24 S23 C27 92.74(13) . . ?
C14 O13 C12 117.2(2) . . ?
C30 O29 C28 115.7(2) . . ?
H32b N32 H32a 120.0 . . ?
C27 N32 H32a 120.0 . . ?
C27 N32 H32b 120.0 . . ?
H16b N16 H16a 120.0 . . ?
C11 N16 H16a 120.0 . . ?
C11 N16 H16b 120.0 . . ?
C8 C1 C6 123.4(2) . . ?
C2 C1 C6 117.6(2) . . ?
C2 C1 C8 118.9(2) . . ?
O29 C28 O31 122.0(3) . . ?
C26 C28 O31 126.2(2) . . ?
C26 C28 O29 111.9(2) . . ?
C22 C17 C24 119.8(3) . . ?
C18 C17 C24 122.4(3) . . ?
C18 C17 C22 117.6(3) . . ?
O15 C12 O13 121.2(3) . . ?
C10 C12 O13 113.1(2) . . ?
C10 C12 O15 125.7(3) . . ?
C27 C26 C28 121.6(2) . . ?
C25 C26 C28 123.5(2) . . ?
C25 C26 C27 114.3(2) . . ?
N16 C11 S7 117.7(2) . . ?
C10 C11 S7 113.8(2) . . ?
C10 C11 N16 128.6(3) . . ?
H6 C6 C1 119.49(15) . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.49(18) . . ?
C1 C8 S7 112.13(18) . . ?
H8 C8 S7 108.01(8) . . ?
H8 C8 C1 108.01(14) . . ?
C9 C8 S7 106.88(16) . . ?
C9 C8 C1 113.6(2) . . ?
C9 C8 H8 108.01(14) . . ?
N32 C27 S23 118.4(2) . . ?
C26 C27 S23 114.0(2) . . ?
C26 C27 N32 127.5(2) . . ?
C11 C10 C12 121.4(2) . . ?
C9 C10 C12 123.1(2) . . ?
C9 C10 C11 115.1(2) . . ?
H2 C2 C1 119.51(16) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.51(19) . . ?
C17 C24 S23 113.3(2) . . ?
H24 C24 S23 108.59(9) . . ?
H24 C24 C17 108.59(15) . . ?
C25 C24 S23 105.87(19) . . ?
C25 C24 C17 111.7(2) . . ?
C25 C24 H24 108.59(17) . . ?
H22 C22 C17 119.29(18) . . ?
C21 C22 C17 121.4(3) . . ?
C21 C22 H22 119.3(2) . . ?
C24 C25 C26 108.8(2) . . ?
H25a C25 C26 109.94(16) . . ?
H25a C25 C24 109.94(16) . . ?
H25b C25 C26 109.94(16) . . ?
H25b C25 C24 109.94(16) . . ?
H25b C25 H25a 108.3 . . ?
H5 C5 C6 119.77(18) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.77(18) . . ?
C10 C9 C8 108.5(2) . . ?
H9a C9 C8 110.00(13) . . ?
H9a C9 C10 110.00(14) . . ?
H9b C9 C8 110.00(14) . . ?
H9b C9 C10 110.00(14) . . ?
H9b C9 H9a 108.4 . . ?
H4 C4 C5 120.44(18) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.44(18) . . ?
C4 C3 C2 120.8(3) . . ?
H3 C3 C2 119.61(19) . . ?
H3 C3 C4 119.61(18) . . ?
H18 C18 C17 119.81(18) . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8(2) . . ?
C21 C20 H20 120.1(2) . . ?
C19 C20 H20 120.1(2) . . ?
C19 C20 C21 119.8(3) . . ?
C20 C21 C22 120.0(3) . . ?
H21 C21 C22 120.0(2) . . ?
H21 C21 C20 120.0(2) . . ?
H14a C14 O13 109.5 . . ?
H14b C14 O13 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 O13 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H30a C30 O29 109.5 . . ?
H30b C30 O29 109.5 . . ?
H30b C30 H30a 109.5 . . ?
H30c C30 O29 109.5 . . ?
H30c C30 H30a 109.5 . . ?
H30c C30 H30b 109.5 . . ?
C20 C19 C18 120.7(4) . . ?
H19 C19 C18 119.6(2) . . ?
H19 C19 C20 119.6(2) . . ?

_olex2_date_sample_data_collection 2017-04-12
_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 1.769
_oxdiff_exptl_absorpt_empirical_full_min 0.672
####################################################################### 
# 
# 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_zgf-20180104
_database_code_depnum_ccdc_archive 'CCDC 1852129'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_audit_creation_date             2018-01-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_chemical_formula_moiety         'C3 H6 N2 O2 S'
_chemical_formula_sum            'C3 H6 N2 O2 S'
_chemical_formula_weight         134.16
_chemical_oxdiff_formula         'C1 H1 O1 S1'
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/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.3625(4)
_cell_length_b                   9.5369(4)
_cell_length_c                   16.9216(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.933(4)
_cell_angle_gamma                90
_cell_volume                     1183.76(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2805
_cell_measurement_temperature    293.67(10)
_cell_measurement_theta_max      28.4420
_cell_measurement_theta_min      3.7860
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5054
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             561.2491
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8001
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.50
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.67(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  55.00   1.00    2.11    --   16.13 -99.00  30.00   75
  2  ω    -53.00  85.00   1.00    2.11    --   16.13   0.00-150.00  138
  3  ω    -85.00   0.00   1.00    2.11    --  -17.23 -57.00-150.00   85
  4  ω    -51.00 -24.00   1.00    2.11    --   16.13 -57.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0344123000
_diffrn_orient_matrix_UB_12      0.0635770000
_diffrn_orient_matrix_UB_13      0.0170970000
_diffrn_orient_matrix_UB_21      0.0102157000
_diffrn_orient_matrix_UB_22      -0.0326383000
_diffrn_orient_matrix_UB_23      0.0377943000
_diffrn_orient_matrix_UB_31      0.0898098000
_diffrn_orient_matrix_UB_32      -0.0206090000
_diffrn_orient_matrix_UB_33      -0.0069614000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -6
_reflns_number_gt                1728
_reflns_number_total             2081
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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)'
_refine_diff_density_max         0.2191
_refine_diff_density_min         -0.2523
_refine_diff_density_rms         0.0687
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.8143
_refine_ls_goodness_of_fit_ref   1.0733
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.0733
_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)+(0.0340P)²+0.5396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0934
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N11(H11)
2.b X=CH2 refined with riding coordinates:
 N15(H15a,H15b), N7(H7a,H7b)
2.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C6(H6a,H6b,H6c)
;
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
S1 S 0.47108(10) 0.20763(6) 0.79172(3) 0.0452(2) Uani 1.000000 .
S9 S 0.11608(11) 0.71070(6) 0.39544(4) 0.0546(2) Uani 1.000000 .
O13 O 0.4659(2) 0.65083(16) 0.64501(9) 0.0400(4) Uani 1.000000 .
O5 O 0.2990(2) 0.15379(16) 0.51454(9) 0.0471(5) Uani 1.000000 .
O16 O 0.3679(2) 0.44167(16) 0.59768(10) 0.0482(5) Uani 1.000000 .
O8 O 0.3005(3) -0.05558(17) 0.57419(10) 0.0588(5) Uani 1.000000 .
N3 N 0.3769(3) 0.14461(19) 0.64299(11) 0.0378(5) Uani 1.000000 .
H3 H 0.3827(3) 0.23409(19) 0.63738(11) 0.0454(6) Uiso 1.000000 R
N11 N 0.2972(3) 0.64504(19) 0.53078(10) 0.0373(5) Uani 1.000000 .
H11 H 0.3080(3) 0.73459(19) 0.53486(10) 0.0448(6) Uiso 1.000000 R
N15 N 0.1856(3) 0.45884(19) 0.45406(11) 0.0404(5) Uani 1.000000 .
H15a H 0.1279(3) 0.42485(19) 0.41203(11) 0.0485(6) Uiso 1.000000 R
H15b H 0.2325(3) 0.40353(19) 0.49043(11) 0.0485(6) Uiso 1.000000 R
N7 N 0.4260(3) -0.0429(2) 0.72844(12) 0.0534(6) Uani 1.000000 .
H7a H 0.4537(3) -0.0773(2) 0.77488(12) 0.0641(7) Uiso 1.000000 R
H7b H 0.4003(3) -0.0978(2) 0.68874(12) 0.0641(7) Uiso 1.000000 R
C12 C 0.3762(3) 0.5677(2) 0.59265(13) 0.0340(5) Uani 1.000000 .
C2 C 0.4231(3) 0.0936(2) 0.71813(13) 0.0337(5) Uani 1.000000 .
C4 C 0.3230(3) 0.0695(2) 0.57626(13) 0.0370(6) Uani 1.000000 .
C10 C 0.2023(3) 0.5956(2) 0.46272(13) 0.0347(5) Uani 1.000000 .
C14 C 0.5486(4) 0.5811(3) 0.71540(14) 0.0492(7) Uani 1.000000 .
H14a H 0.618(2) 0.5019(11) 0.70003(14) 0.0739(10) Uiso 1.000000 GR
H14b H 0.6278(19) 0.6454(6) 0.7453(5) 0.0739(10) Uiso 1.000000 GR
H14c H 0.4549(4) 0.5501(16) 0.7474(5) 0.0739(10) Uiso 1.000000 GR
C6 C 0.2246(4) 0.0910(3) 0.44075(14) 0.0557(8) Uani 1.000000 .
H6a H 0.258(2) 0.1467(11) 0.39699(14) 0.0836(12) Uiso 1.000000 GR
H6b H 0.272(2) -0.0021(8) 0.4365(5) 0.0836(12) Uiso 1.000000 GR
H6c H 0.0942(5) 0.0868(18) 0.4399(5) 0.0836(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
S1 C2 1.668(2) . ?
S9 C10 1.667(2) . ?
O13 C12 1.323(3) . ?
O13 C14 1.451(3) . ?
O5 C4 1.317(3) . ?
O5 C6 1.449(3) . ?
O16 C12 1.207(3) . ?
O8 C4 1.205(3) . ?
N3 H3 0.8600 . ?
N3 C2 1.376(3) . ?
N3 C4 1.367(3) . ?
N11 H11 0.8600 . ?
N11 C12 1.369(3) . ?
N11 C10 1.378(3) . ?
N15 H15a 0.8600 . ?
N15 H15b 0.8600 . ?
N15 C10 1.317(3) . ?
N7 H7a 0.8600 . ?
N7 H7b 0.8600 . ?
N7 C2 1.313(3) . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C6 H6a 0.9600 . ?
C6 H6b 0.9600 . ?
C6 H6c 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
C14 O13 C12 115.17(18) . . ?
C6 O5 C4 116.48(18) . . ?
C2 N3 H3 116.23(12) . . ?
C4 N3 H3 116.23(12) . . ?
C4 N3 C2 127.53(19) . . ?
C12 N11 H11 116.33(12) . . ?
C10 N11 H11 116.33(12) . . ?
C10 N11 C12 127.33(19) . . ?
H15b N15 H15a 120.0 . . ?
C10 N15 H15a 120.0 . . ?
C10 N15 H15b 120.0 . . ?
H7b N7 H7a 120.0 . . ?
C2 N7 H7a 120.0 . . ?
C2 N7 H7b 120.0 . . ?
O16 C12 O13 125.1(2) . . ?
N11 C12 O13 110.11(18) . . ?
N11 C12 O16 124.7(2) . . ?
N3 C2 S1 118.62(16) . . ?
N7 C2 S1 123.16(17) . . ?
N7 C2 N3 118.2(2) . . ?
O8 C4 O5 124.9(2) . . ?
N3 C4 O5 110.19(18) . . ?
N3 C4 O8 124.9(2) . . ?
N11 C10 S9 118.79(16) . . ?
N15 C10 S9 123.34(17) . . ?
N15 C10 N11 117.9(2) . . ?
H14a C14 O13 109.5 . . ?
H14b C14 O13 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 O13 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H6a C6 O5 109.5 . . ?
H6b C6 O5 109.5 . . ?
H6b C6 H6a 109.5 . . ?
H6c C6 O5 109.5 . . ?
H6c C6 H6a 109.5 . . ?
H6c C6 H6b 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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.563
####################################################################### 
# 
# 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_zgf-20171208
_database_code_depnum_ccdc_archive 'CCDC 1852131'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_audit_creation_date             2017-12-11
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C16 H20 N2 O6 S'
_chemical_formula_sum            'C16 H20 N2 O6 S'
_chemical_formula_weight         368.41
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   14.0809(10)
_cell_length_b                   12.1296(5)
_cell_length_c                   21.4422(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3662.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3912
_cell_measurement_temperature    291.37(11)
_cell_measurement_theta_max      27.5770
_cell_measurement_theta_min      3.8360
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3363
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             1553.8721
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12723
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.35
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.37(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  87.00   1.00    6.11    --   16.13-178.00 -30.00   38
  2  ω    -41.00   9.00   1.00    6.11    --   16.13   0.00 -90.00   50
  3  ω     17.00  72.00   1.00    6.11    --   16.13   0.00 -90.00   55
  4  ω     57.00  89.00   1.00    6.11    --   16.13-178.00  90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0338723000
_diffrn_orient_matrix_UB_12      -0.0064074000
_diffrn_orient_matrix_UB_13      -0.0242433000
_diffrn_orient_matrix_UB_21      0.0313475000
_diffrn_orient_matrix_UB_22      0.0362722000
_diffrn_orient_matrix_UB_23      0.0157551000
_diffrn_orient_matrix_UB_31      0.0202043000
_diffrn_orient_matrix_UB_32      -0.0454138000
_diffrn_orient_matrix_UB_33      0.0160740000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                2516
_reflns_number_total             3212
_reflns_odcompleteness_completeness 98.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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)'
_refine_diff_density_max         0.3072
_refine_diff_density_min         -0.3634
_refine_diff_density_rms         0.0587
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.0891
_refine_ls_goodness_of_fit_ref   1.0479
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.0479
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+1.0242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1385
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N20(H20a,H20b)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.d Aromatic/amide H refined with riding coordinates:
 N11(H11), C6(H6), C2(H2), C5(H5), C4(H4), C3(H3)
2.e Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c), C18(H18a,H18b,H18c), C14(H14a,H14b,H14c)
;
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
S21 S 0.56220(5) 0.43354(4) 0.36427(3) 0.0522(2) Uani 1.000000 .
O25 O 0.60997(13) 0.42482(12) 0.48384(7) 0.0517(4) Uani 1.000000 .
O17 O 0.66274(13) 0.82277(13) 0.32230(7) 0.0566(5) Uani 1.000000 .
O23 O 0.60291(14) 0.26754(13) 0.42833(8) 0.0580(5) Uani 1.000000 .
O15 O 0.62193(15) 0.82167(15) 0.61599(8) 0.0669(6) Uani 1.000000 .
O19 O 0.64313(16) 0.94189(13) 0.40068(9) 0.0697(6) Uani 1.000000 .
N20 N 0.62839(15) 0.66965(15) 0.52334(9) 0.0501(5) Uani 1.000000 .
H20a H 0.6033(12) 0.6892(4) 0.5584(3) 0.0602(6) Uiso 1.000000 GR
H20b H 0.5939(11) 0.6188(6) 0.5067(4) 0.0602(6) Uiso 1.000000 GR
N11 N 0.62883(16) 0.86064(15) 0.51208(9) 0.0535(6) Uani 1.000000 .
H11 H 0.62977(16) 0.91593(15) 0.48698(9) 0.0641(7) Uiso 1.000000 R
O13 O 0.62165(18) 0.99470(14) 0.57945(9) 0.0832(7) Uani 1.000000 .
C22 C 0.59677(17) 0.37684(18) 0.43605(11) 0.0437(5) Uani 1.000000 .
C10 C 0.63249(16) 0.75724(17) 0.48417(11) 0.0418(5) Uani 1.000000 .
C9 C 0.64154(16) 0.74799(17) 0.42106(10) 0.0405(5) Uani 1.000000 .
C1 C 0.48541(16) 0.62667(16) 0.33615(10) 0.0403(5) Uani 1.000000 .
C7 C 0.55013(17) 0.57899(16) 0.38577(10) 0.0392(5) Uani 1.000000 .
H7 H 0.51739(17) 0.58319(16) 0.42603(10) 0.0471(6) Uiso 1.000000 R
C8 C 0.64737(17) 0.63452(17) 0.39241(10) 0.0424(5) Uani 1.000000 .
H8a H 0.67652(17) 0.64024(17) 0.35155(10) 0.0509(6) Uiso 1.000000 R
H8b H 0.68790(17) 0.58850(17) 0.41811(10) 0.0509(6) Uiso 1.000000 R
C16 C 0.64873(18) 0.84566(19) 0.38275(11) 0.0473(6) Uani 1.000000 .
C6 C 0.51759(19) 0.65006(19) 0.27651(10) 0.0501(6) Uani 1.000000 .
H6 H 0.58125(19) 0.63885(19) 0.26685(10) 0.0601(7) Uiso 1.000000 R
C2 C 0.38994(18) 0.64301(19) 0.34886(11) 0.0493(6) Uani 1.000000 .
H2 H 0.36623(18) 0.62707(19) 0.38833(11) 0.0591(7) Uiso 1.000000 R
C12 C 0.62403(19) 0.8857(2) 0.57312(12) 0.0544(6) Uani 1.000000 .
C5 C 0.4571(2) 0.6896(2) 0.23132(12) 0.0595(7) Uani 1.000000 .
H5 H 0.4801(2) 0.7049(2) 0.19158(12) 0.0714(9) Uiso 1.000000 R
C4 C 0.3634(2) 0.7063(2) 0.24475(13) 0.0600(7) Uani 1.000000 .
H4 H 0.3227(2) 0.7335(2) 0.21428(13) 0.0720(9) Uiso 1.000000 R
C3 C 0.3296(2) 0.6830(2) 0.30303(13) 0.0589(7) Uani 1.000000 .
H3 H 0.2657(2) 0.6940(2) 0.31200(13) 0.0707(8) Uiso 1.000000 R
C24 C 0.6216(2) 0.2027(2) 0.48356(13) 0.0617(7) Uani 1.000000 .
H24a H 0.6297(14) 0.1268(3) 0.47207(17) 0.0925(11) Uiso 1.000000 GR
H24b H 0.6784(8) 0.2289(10) 0.5034(5) 0.0925(11) Uiso 1.000000 GR
H24c H 0.5691(6) 0.2092(13) 0.5119(4) 0.0925(11) Uiso 1.000000 GR
C18 C 0.6666(3) 0.9151(2) 0.28023(14) 0.0788(10) Uani 1.000000 .
H18a H 0.6759(17) 0.8889(3) 0.23842(19) 0.1182(15) Uiso 1.000000 GR
H18b H 0.6081(7) 0.9555(11) 0.2825(8) 0.1182(15) Uiso 1.000000 GR
H18c H 0.7183(10) 0.9624(10) 0.2917(7) 0.1182(15) Uiso 1.000000 GR
C14 C 0.6123(4) 1.0367(3) 0.64201(15) 0.1092(15) Uani 1.000000 .
H14a H 0.598(2) 1.1141(6) 0.64052(15) 0.164(2) Uiso 1.000000 GR
H14b H 0.5617(15) 0.9987(19) 0.6629(5) 0.164(2) Uiso 1.000000 GR
H14c H 0.6706(8) 1.025(2) 0.6643(5) 0.164(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
S21 C22 1.755(2) . ?
S21 C7 1.831(2) . ?
O25 C22 1.193(3) . ?
O17 C16 1.340(3) . ?
O17 C18 1.439(3) . ?
O23 C22 1.339(3) . ?
O23 C24 1.446(3) . ?
O15 C12 1.204(3) . ?
O19 C16 1.231(3) . ?
N20 H20a 0.8628 . ?
N20 H20b 0.8622 . ?
N20 C10 1.356(3) . ?
N11 H11 0.8600 . ?
N11 C10 1.391(3) . ?
N11 C12 1.345(3) . ?
O13 C12 1.329(3) . ?
O13 C14 1.441(3) . ?
C10 C9 1.364(3) . ?
C9 C8 1.509(3) . ?
C9 C16 1.445(3) . ?
C1 C7 1.516(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.386(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.533(3) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.376(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.365(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.367(4) . ?
C3 H3 0.9300 . ?
C24 H24a 0.9600 . ?
C24 H24b 0.9600 . ?
C24 H24c 0.9600 . ?
C18 H18a 0.9600 . ?
C18 H18b 0.9600 . ?
C18 H18c 0.9600 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 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
C7 S21 C22 100.51(10) . . ?
C18 O17 C16 116.8(2) . . ?
C24 O23 C22 116.7(2) . . ?
H20b N20 H20a 109.1 . . ?
C10 N20 H20a 110.0 . . ?
C10 N20 H20b 109.1 . . ?
C10 N11 H11 115.68(12) . . ?
C12 N11 H11 115.68(13) . . ?
C12 N11 C10 128.6(2) . . ?
C14 O13 C12 116.7(2) . . ?
O25 C22 S21 127.26(17) . . ?
O23 C22 S21 107.31(17) . . ?
O23 C22 O25 125.4(2) . . ?
N11 C10 N20 116.0(2) . . ?
C9 C10 N20 123.7(2) . . ?
C9 C10 N11 120.31(19) . . ?
C8 C9 C10 118.95(19) . . ?
C16 C9 C10 120.2(2) . . ?
C16 C9 C8 120.82(19) . . ?
C6 C1 C7 122.0(2) . . ?
C2 C1 C7 120.0(2) . . ?
C2 C1 C6 118.0(2) . . ?
C1 C7 S21 104.28(14) . . ?
H7 C7 S21 108.39(7) . . ?
H7 C7 C1 108.39(12) . . ?
C8 C7 S21 111.34(15) . . ?
C8 C7 C1 115.77(17) . . ?
C8 C7 H7 108.39(12) . . ?
C7 C8 C9 112.95(18) . . ?
H8a C8 C9 108.99(12) . . ?
H8a C8 C7 108.99(12) . . ?
H8b C8 C9 108.99(12) . . ?
H8b C8 C7 108.99(11) . . ?
H8b C8 H8a 107.8 . . ?
O19 C16 O17 120.5(2) . . ?
C9 C16 O17 112.96(19) . . ?
C9 C16 O19 126.5(2) . . ?
H6 C6 C1 119.38(14) . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.38(16) . . ?
H2 C2 C1 119.83(13) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.83(16) . . ?
N11 C12 O15 126.7(2) . . ?
O13 C12 O15 124.3(2) . . ?
O13 C12 N11 109.0(2) . . ?
H5 C5 C6 119.96(16) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.96(15) . . ?
H4 C4 C5 120.03(15) . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.03(17) . . ?
C4 C3 C2 120.4(3) . . ?
H3 C3 C2 119.79(16) . . ?
H3 C3 C4 119.79(17) . . ?
H24a C24 O23 109.5 . . ?
H24b C24 O23 109.5 . . ?
H24b C24 H24a 109.5 . . ?
H24c C24 O23 109.5 . . ?
H24c C24 H24a 109.5 . . ?
H24c C24 H24b 109.5 . . ?
H18a C18 O17 109.5 . . ?
H18b C18 O17 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 O17 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H14a C14 O13 109.5 . . ?
H14b C14 O13 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 O13 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 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 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.629
