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

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

data_lzh-20220328
_database_code_depnum_ccdc_archive 'CCDC 2191368'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2022-06-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 N2 O3 S'
_chemical_formula_sum            'C11 H14 N2 O3 S'
_chemical_formula_weight         254.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9547(2)
_cell_length_b                   8.41310(10)
_cell_length_c                   16.3860(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.853(2)
_cell_angle_gamma                90
_cell_volume                     1216.26(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2938
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2140
_cell_measurement_theta_min      5.2830
_shelx_estimated_absorpt_T_max   0.648
_shelx_estimated_absorpt_T_min   0.536
_exptl_absorpt_coefficient_mu    2.376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5020
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.480
_diffrn_reflns_theta_min         5.286
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -18.00   1.00    1.00    --  -35.62 -41.00-122.00   86
  2  ω    -46.00  -3.00   1.00    1.00    --  -35.62  41.00  30.00   43
  3  ω    -14.00  11.00   1.00    1.00    --   35.62 -41.00-122.00   25
  4  ω     45.00 102.00   1.00    1.00    --   35.62  41.00  30.00   57
  5  ω     38.00 123.00   1.00    1.02    --  107.12 -41.00-122.00   85
  6  ω     95.00 124.00   1.00    1.02    --  107.12  41.00  30.00   29
  7  ω    -68.00 -36.00   1.00    1.00    --  -35.62-178.00 -60.00   32
  8  ω    -28.00  52.00   1.00    1.00    --   35.62 -38.00  90.00   80
  9  ω     55.00 105.00   1.00    1.00    --   35.62-178.00-180.00   50
 10  ω     64.00 122.00   1.00    1.02    --  107.12 -45.00  90.00   58
 11  ω     43.00 104.00   1.00    1.02    --  107.12 -77.00 120.00   61
 12  ω    104.00 167.00   1.00    1.02    --  107.12  61.00  30.00   63
 13  ω     44.00  97.00   1.00    1.02    --  107.12 -95.00-120.00   53
 14  ω     72.00 161.00   1.00    1.02    --  107.12  15.00 -30.00   89
 15  ω     48.00  75.00   1.00    1.02    --  107.12 -95.00  30.00   27
 16  ω     39.00 116.00   1.00    1.02    --  107.12 -45.00  30.00   77
;
_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      0.0317046000
_diffrn_orient_matrix_UB_12      0.0671016000
_diffrn_orient_matrix_UB_13      0.0887730000
_diffrn_orient_matrix_UB_21      -0.1518612000
_diffrn_orient_matrix_UB_22      -0.0685496000
_diffrn_orient_matrix_UB_23      0.0161661000
_diffrn_orient_matrix_UB_31      0.0802871000
_diffrn_orient_matrix_UB_32      -0.1558991000
_diffrn_orient_matrix_UB_33      0.0310460000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2056
_reflns_number_total             2313
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0687P)²+0.1811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1169
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.62964(5) 0.63736(5) 0.38230(3) 0.03911(19) Uani 1 1 d . . . . .
O10 O 0.66052(13) 0.78208(15) 0.32229(8) 0.0416(3) Uani 1 1 d . . . . .
O11 O 0.58912(16) 0.50119(17) 0.33171(9) 0.0519(4) Uani 1 1 d . . . . .
O12 O 0.76512(17) 0.62929(19) 0.44151(10) 0.0566(4) Uani 1 1 d . . . . .
N13 N 0.27455(17) 0.83385(17) 0.42073(9) 0.0382(4) Uani 1 1 d . . . . .
N2 N 0.49565(18) 0.69998(18) 0.42497(9) 0.0404(4) Uani 1 1 d . . . . .
C9 C 0.53047(19) 0.8297(2) 0.26826(11) 0.0359(4) Uani 1 1 d . . . . .
C4 C 0.3900(2) 0.8288(2) 0.29391(11) 0.0349(4) Uani 1 1 d . . . . .
C3 C 0.38519(19) 0.78664(19) 0.38137(11) 0.0340(4) Uani 1 1 d . . . . .
C5 C 0.2633(2) 0.8606(2) 0.23324(12) 0.0420(4) Uani 1 1 d . . . . .
H5 H 0.166715 0.853994 0.246688 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5493(2) 0.8763(2) 0.18985(12) 0.0451(5) Uani 1 1 d . . . . .
H8 H 0.645466 0.881671 0.175754 0.054 Uiso 1 1 calc R U . . .
C6 C 0.2799(2) 0.9018(3) 0.15358(12) 0.0486(5) Uani 1 1 d . . . . .
H6 H 0.194543 0.920951 0.113780 0.058 Uiso 1 1 calc R U . . .
C16 C 0.2736(2) 0.7743(2) 0.50520(11) 0.0460(5) Uani 1 1 d . . . . .
H16A H 0.305529 0.663998 0.508186 0.055 Uiso 1 1 calc R U . . .
H16B H 0.170727 0.778270 0.516350 0.055 Uiso 1 1 calc R U . . .
C14 C 0.1722(2) 0.9694(2) 0.39612(13) 0.0484(5) Uani 1 1 d . . . . .
H14A H 0.201063 1.020461 0.348061 0.058 Uiso 1 1 calc R U . . .
H14B H 0.184521 1.046442 0.440804 0.058 Uiso 1 1 calc R U . . .
C7 C 0.4223(2) 0.9146(3) 0.13282(12) 0.0514(5) Uani 1 1 d . . . . .
H7 H 0.432900 0.949254 0.080211 0.062 Uiso 1 1 calc R U . . .
C17 C 0.3758(3) 0.8677(3) 0.57152(14) 0.0620(6) Uani 1 1 d . . . . .
H17A H 0.478395 0.861935 0.561879 0.093 Uiso 1 1 calc R U . . .
H17B H 0.369935 0.823650 0.624924 0.093 Uiso 1 1 calc R U . . .
H17C H 0.343699 0.976722 0.569775 0.093 Uiso 1 1 calc R U . . .
C15 C 0.0066(3) 0.9211(4) 0.37570(17) 0.0740(8) Uani 1 1 d . . . . .
H15A H -0.007205 0.847930 0.330096 0.111 Uiso 1 1 calc R U . . .
H15B H -0.054742 1.013779 0.360964 0.111 Uiso 1 1 calc R U . . .
H15C H -0.023067 0.871250 0.423147 0.111 Uiso 1 1 calc R U . . .


_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
S1 O10 1.6183(13) . ?
S1 O11 1.4242(14) . ?
S1 O12 1.4195(14) . ?
S1 N2 1.5790(16) . ?
O10 C9 1.3955(19) . ?
N13 C3 1.332(2) . ?
N13 C16 1.473(2) . ?
N13 C14 1.475(2) . ?
N2 C3 1.334(2) . ?
C9 C4 1.393(2) . ?
C9 C8 1.381(3) . ?
C4 C3 1.484(2) . ?
C4 C5 1.400(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.381(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.519(3) . ?
C7 H7 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O11 S1 O10 107.73(8) . . ?
O11 S1 N2 112.89(9) . . ?
O12 S1 O10 103.67(8) . . ?
O12 S1 O11 117.53(9) . . ?
O12 S1 N2 109.79(9) . . ?
N2 S1 O10 103.88(7) . . ?
C9 O10 S1 112.99(10) . . ?
C3 N13 C16 118.55(16) . . ?
C3 N13 C14 125.22(15) . . ?
C16 N13 C14 114.61(15) . . ?
C3 N2 S1 119.69(13) . . ?
C4 C9 O10 120.40(16) . . ?
C8 C9 O10 116.75(16) . . ?
C8 C9 C4 122.85(17) . . ?
C9 C4 C3 117.98(16) . . ?
C9 C4 C5 116.65(16) . . ?
C5 C4 C3 125.29(16) . . ?
N13 C3 N2 116.65(16) . . ?
N13 C3 C4 122.89(15) . . ?
N2 C3 C4 120.45(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.88(18) . . ?
C6 C5 H5 119.6 . . ?
C9 C8 H8 120.7 . . ?
C7 C8 C9 118.59(18) . . ?
C7 C8 H8 120.7 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.38(18) . . ?
C7 C6 H6 119.8 . . ?
N13 C16 H16A 108.9 . . ?
N13 C16 H16B 108.9 . . ?
N13 C16 C17 113.44(16) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
N13 C14 H14A 109.0 . . ?
N13 C14 H14B 109.0 . . ?
N13 C14 C15 113.02(18) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.26(18) . . ?
C6 C7 H7 119.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 O10 C9 C4 36.1(2) . . . . ?
S1 O10 C9 C8 -143.85(15) . . . . ?
S1 N2 C3 N13 179.10(12) . . . . ?
S1 N2 C3 C4 -1.9(2) . . . . ?
O10 S1 N2 C3 37.68(16) . . . . ?
O10 C9 C4 C3 4.1(2) . . . . ?
O10 C9 C4 C5 -172.88(15) . . . . ?
O10 C9 C8 C7 175.96(17) . . . . ?
O11 S1 O10 C9 65.82(13) . . . . ?
O11 S1 N2 C3 -78.73(16) . . . . ?
O12 S1 O10 C9 -168.93(12) . . . . ?
O12 S1 N2 C3 148.03(14) . . . . ?
N2 S1 O10 C9 -54.15(13) . . . . ?
C9 C4 C3 N13 155.51(17) . . . . ?
C9 C4 C3 N2 -23.4(2) . . . . ?
C9 C4 C5 C6 -4.5(3) . . . . ?
C9 C8 C7 C6 -1.9(3) . . . . ?
C4 C9 C8 C7 -4.0(3) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C3 N13 C16 C17 83.2(2) . . . . ?
C3 N13 C14 C15 119.3(2) . . . . ?
C3 C4 C5 C6 178.83(18) . . . . ?
C5 C4 C3 N13 -27.8(3) . . . . ?
C5 C4 C3 N2 153.27(17) . . . . ?
C5 C6 C7 C8 4.3(3) . . . . ?
C8 C9 C4 C3 -176.02(17) . . . . ?
C8 C9 C4 C5 7.0(3) . . . . ?
C16 N13 C3 N2 -6.2(2) . . . . ?
C16 N13 C3 C4 174.91(16) . . . . ?
C16 N13 C14 C15 -75.5(2) . . . . ?
C14 N13 C3 N2 158.52(18) . . . . ?
C14 N13 C3 C4 -20.4(3) . . . . ?
C14 N13 C16 C17 -83.1(2) . . . . ?

_olex2_date_sample_data_collection 2022-03-28
_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 1.954
_oxdiff_exptl_absorpt_empirical_full_min 0.596
####################################################################### 
# 
# 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_3-76
_database_code_depnum_ccdc_archive 'CCDC 2191372'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2022-04-07
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 N2 O3 S'
_chemical_formula_sum            'C13 H10 N2 O3 S'
_chemical_formula_weight         274.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9208(9)
_cell_length_b                   7.4115(6)
_cell_length_c                   11.9359(12)
_cell_angle_alpha                101.965(7)
_cell_angle_beta                 90.131(9)
_cell_angle_gamma                92.439(8)
_cell_volume                     598.35(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2242
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.4330
_cell_measurement_theta_min      3.7240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63163
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3550
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         3.786
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  56.00   1.00    1.00    --   40.73 -99.00 -90.00   43
  2  ω     23.00  59.00   1.00    1.00    --   40.73-125.00   0.00   36
  3  ω     28.00  95.00   1.00    1.00    --   40.73-125.00  90.00   67
  4  ω     35.00 137.00   1.00    1.50    --  107.58 -61.00   0.00  102
  5  ω     80.00 106.00   1.00    1.50    --  107.58 -94.00   0.00   26
  6  ω     41.00 129.00   1.00    1.50    --  107.58 -45.00  90.00   88
  7  ω     89.00 158.00   1.00    1.50    --  107.58  45.00  90.00   69
  8  ω    117.00 177.00   1.00    1.50    --  107.58 125.00 -90.00   60
  9  ω    111.00 137.00   1.00    1.50    --  107.58 125.00-180.00   26
 10  ω     59.00 178.00   1.00    1.50    --  107.58  15.00  30.00  119
 11  ω     93.00 133.00   1.00    1.50    --  107.58 -45.00-180.00   40
 12  ω     72.00 105.00   1.00    1.50    --  107.58 -94.00-180.00   33
 13  ω     46.00  73.00   1.00    1.50    --  107.58 -45.00-180.00   27
 14  ω     26.00 108.00   1.00    1.50    --  107.58 -94.00 -90.00   82
 15  ω     45.00  86.00   1.00    1.50    --  107.58 -61.00 -60.00   41
 16  ω   -115.00 -17.00   1.00    1.00    --  -40.73 -38.00 120.00   98
 17  ω   -120.00  -6.00   1.00    1.00    --  -40.73 -19.00-180.00  114
 18  ω    -35.00 -18.00   1.00    1.00    --  -41.23 125.00 -90.00   17
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0779135000
_diffrn_orient_matrix_UB_12      -0.0286007000
_diffrn_orient_matrix_UB_13      -0.1229534000
_diffrn_orient_matrix_UB_21      -0.2015039000
_diffrn_orient_matrix_UB_22      0.0348271000
_diffrn_orient_matrix_UB_23      -0.0441805000
_diffrn_orient_matrix_UB_31      0.0545192000
_diffrn_orient_matrix_UB_32      0.2078524000
_diffrn_orient_matrix_UB_33      0.0185105000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1990
_reflns_number_total             2102
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.1261
_refine_ls_restrained_S_all      1.205
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+10.9144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3218
_refine_ls_wR_factor_ref         0.3232
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Sof(H11A)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=
 Sof(H12B)=1-FVAR(1)
 Sof(C13)=Sof(H13)=Sof(C12)=Sof(H12)=Sof(H11)=Sof(C10)=Sof(H10)=Sof(C9)=
 Sof(H9)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C13(H13), C12(H12), C11(H11A),
 C11(H11), C10(H10), C9(H9), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
3.b Fitted hexagon refined as free rotating group:
 C8(C13,C12,C11,C10,C9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.73637(19) 0.13569(16) 0.65822(10) 0.0241(3) Uani 1 1 d . . . . .
O1 O 0.8249(6) 0.1385(5) 0.5346(3) 0.0315(10) Uani 1 1 d . . . . .
O2 O 0.5385(6) 0.0759(6) 0.6410(4) 0.0426(12) Uani 1 1 d . . . . .
O3 O 0.8598(6) 0.0183(5) 0.7036(4) 0.0387(11) Uani 1 1 d . . . . .
N1 N 0.7586(7) 0.3391(5) 0.7301(4) 0.0274(11) Uani 1 1 d . . . . .
N2 N 0.7596(6) 0.6516(5) 0.7453(3) 0.0229(10) Uani 1 1 d . . . . .
H2 H 0.764396 0.742215 0.710397 0.027 Uiso 1 1 calc R U . . .
C1 C 0.7871(7) 0.2870(7) 0.4858(4) 0.0226(12) Uani 1 1 d . . . . .
C2 C 0.7849(7) 0.2538(7) 0.3686(5) 0.0299(14) Uani 1 1 d . . . . .
H2A H 0.798836 0.135831 0.324736 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7602(8) 0.4087(8) 0.3169(5) 0.0332(14) Uani 1 1 d . . . . .
H3 H 0.763297 0.393074 0.237592 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7324(8) 0.5774(7) 0.3818(4) 0.0282(13) Uani 1 1 d . . . . .
H4 H 0.714437 0.676187 0.346400 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7301(7) 0.6062(7) 0.5007(4) 0.0261(13) Uani 1 1 d . . . . .
H5 H 0.711478 0.723781 0.543877 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7552(7) 0.4621(6) 0.5551(4) 0.0215(12) Uani 1 1 d . . . . .
C7 C 0.7589(7) 0.4813(6) 0.6793(4) 0.0192(11) Uani 1 1 d . . . . .
C8 C 0.7532(5) 0.6976(5) 0.8670(3) 0.0234(12) Uani 1 1 d G . . . .
C13 C 0.6264(8) 0.8313(7) 0.9163(4) 0.038(3) Uani 0.503(5) 1 d G . P A 1
H13 H 0.547415 0.884233 0.869958 0.045 Uiso 0.503(5) 1 calc R U P A 1
C12 C 0.6176(10) 0.8858(9) 1.0347(4) 0.047(4) Uani 0.503(5) 1 d G . P A 1
H12 H 0.532735 0.975223 1.067692 0.056 Uiso 0.503(5) 1 calc R U P A 1
C11 C 0.7356(10) 0.8067(8) 1.1039(3) 0.052(2) Uani 1 1 d G . . A .
H11A H 0.709732 0.862858 1.179226 0.063 Uiso 0.497(5) 1 calc R U P A 2
H11 H 0.729704 0.843128 1.183205 0.063 Uiso 0.503(5) 1 calc R U P A 1
C10 C 0.8624(10) 0.6730(9) 1.0547(3) 0.046(4) Uani 0.503(5) 1 d G . P A 1
H10 H 0.941354 0.620043 1.100984 0.056 Uiso 0.503(5) 1 calc R U P A 1
C9 C 0.8712(8) 0.6185(7) 0.9362(4) 0.037(3) Uani 0.503(5) 1 d G . P A 1
H9 H 0.956036 0.529050 0.903249 0.044 Uiso 0.503(5) 1 calc R U P A 1
C9B C 0.6233(18) 0.6027(15) 0.9314(9) 0.035(3) Uani 0.497(5) 1 d . . P A 2
H9B H 0.538734 0.507929 0.894524 0.041 Uiso 0.497(5) 1 calc R U P A 2
C10B C 0.627(2) 0.6561(17) 1.0500(9) 0.043(3) Uani 0.497(5) 1 d . . P A 2
H10B H 0.554390 0.587794 1.093317 0.051 Uiso 0.497(5) 1 calc R U P A 2
C11B C 0.8899(18) 0.8243(15) 0.9270(9) 0.034(3) Uani 0.497(5) 1 d . . P A 2
H11B H 0.985833 0.875314 0.887161 0.040 Uiso 0.497(5) 1 calc R U P A 2
C12B C 0.886(2) 0.8756(17) 1.0453(10) 0.044(4) Uani 0.497(5) 1 d . . P A 2
H12B H 0.981660 0.955231 1.085024 0.052 Uiso 0.497(5) 1 calc R U P A 2


_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
S1 O1 1.603(4) . ?
S1 O2 1.422(4) . ?
S1 O3 1.427(4) . ?
S1 N1 1.573(4) . ?
O1 C1 1.381(6) . ?
N1 C7 1.320(6) . ?
N2 H2 0.8600 . ?
N2 C7 1.341(6) . ?
N2 C8 1.423(5) . ?
C1 C2 1.370(7) . ?
C1 C6 1.413(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.428(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.349(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(7) . ?
C6 C7 1.460(7) . ?
C8 C13 1.3900 . ?
C8 C9 1.3900 . ?
C8 C9B 1.438(12) . ?
C8 C11B 1.390(11) . ?
C13 H13 0.9300 . ?
C13 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C11 H11A 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C11 C10B 1.361(14) . ?
C11 C12B 1.391(15) . ?
C10 H10 0.9300 . ?
C10 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9B H9B 0.9300 . ?
C9B C10B 1.389(15) . ?
C10B H10B 0.9300 . ?
C11B H11B 0.9300 . ?
C11B C12B 1.384(15) . ?
C12B H12B 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
O2 S1 O1 107.1(2) . . ?
O2 S1 O3 116.8(3) . . ?
O2 S1 N1 111.4(2) . . ?
O3 S1 O1 103.6(2) . . ?
O3 S1 N1 110.4(2) . . ?
N1 S1 O1 106.6(2) . . ?
C1 O1 S1 117.8(3) . . ?
C7 N1 S1 120.9(4) . . ?
C7 N2 H2 116.7 . . ?
C7 N2 C8 126.7(4) . . ?
C8 N2 H2 116.7 . . ?
O1 C1 C6 120.8(4) . . ?
C2 C1 O1 116.1(4) . . ?
C2 C1 C6 123.1(5) . . ?
C1 C2 H2A 121.6 . . ?
C1 C2 C3 116.9(5) . . ?
C3 C2 H2A 121.6 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(5) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 118.5(4) . . ?
C5 C6 C1 117.6(5) . . ?
C5 C6 C7 123.9(4) . . ?
N1 C7 N2 118.3(4) . . ?
N1 C7 C6 123.2(4) . . ?
N2 C7 C6 118.5(4) . . ?
N2 C8 C9B 122.1(5) . . ?
C13 C8 N2 117.4(3) . . ?
C13 C8 C9 120.0 . . ?
C9 C8 N2 122.6(3) . . ?
C11B C8 N2 119.4(6) . . ?
C11B C8 C9B 118.1(7) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10B C11 H11A 120.3 . . ?
C10B C11 C12B 119.3(7) . . ?
C12B C11 H11A 120.3 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9B H9B 120.8 . . ?
C10B C9B C8 118.3(9) . . ?
C10B C9B H9B 120.8 . . ?
C11 C10B C9B 121.1(10) . . ?
C11 C10B H10B 119.4 . . ?
C9B C10B H10B 119.4 . . ?
C8 C11B H11B 119.5 . . ?
C12B C11B C8 121.0(10) . . ?
C12B C11B H11B 119.5 . . ?
C11 C12B H12B 120.4 . . ?
C11B C12B C11 119.2(10) . . ?
C11B C12B H12B 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 O1 C1 C2 -151.9(4) . . . . ?
S1 O1 C1 C6 28.8(6) . . . . ?
S1 N1 C7 N2 173.7(4) . . . . ?
S1 N1 C7 C6 -5.2(7) . . . . ?
O1 S1 N1 C7 28.7(5) . . . . ?
O1 C1 C2 C3 -175.5(4) . . . . ?
O1 C1 C6 C5 176.1(4) . . . . ?
O1 C1 C6 C7 -1.4(7) . . . . ?
O2 S1 O1 C1 79.2(4) . . . . ?
O2 S1 N1 C7 -87.9(5) . . . . ?
O3 S1 O1 C1 -156.7(3) . . . . ?
O3 S1 N1 C7 140.6(4) . . . . ?
N1 S1 O1 C1 -40.2(4) . . . . ?
N2 C8 C13 C12 -178.2(3) . . . . ?
N2 C8 C9 C10 178.1(3) . . . . ?
N2 C8 C9B C10B 179.7(9) . . . . ?
N2 C8 C11B C12B 178.5(9) . . . . ?
C1 C2 C3 C4 -2.7(8) . . . . ?
C1 C6 C7 N1 -11.6(7) . . . . ?
C1 C6 C7 N2 169.5(4) . . . . ?
C2 C1 C6 C5 -3.1(7) . . . . ?
C2 C1 C6 C7 179.4(5) . . . . ?
C2 C3 C4 C5 1.1(8) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C4 C5 C6 C1 1.3(7) . . . . ?
C4 C5 C6 C7 178.6(5) . . . . ?
C5 C6 C7 N1 171.1(5) . . . . ?
C5 C6 C7 N2 -7.8(7) . . . . ?
C6 C1 C2 C3 3.8(7) . . . . ?
C7 N2 C8 C13 -134.4(5) . . . . ?
C7 N2 C8 C9 47.4(6) . . . . ?
C7 N2 C8 C9B -44.4(9) . . . . ?
C7 N2 C8 C11B 128.6(7) . . . . ?
C8 N2 C7 N1 -2.4(7) . . . . ?
C8 N2 C7 C6 176.6(4) . . . . ?
C8 C13 C12 C11 0.0 . . . . ?
C8 C9B C10B C11 6.9(18) . . . . ?
C8 C11B C12B C11 -3.5(18) . . . . ?
C13 C8 C9 C10 0.0 . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C12 C11 C10 C9 0.0 . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
C9B C8 C11B C12B -8.3(15) . . . . ?
C10B C11 C12B C11B 17.2(17) . . . . ?
C11B C8 C9B C10B 6.7(14) . . . . ?
C12B C11 C10B C9B -19.0(18) . . . . ?

_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 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.489
####################################################################### 
# 
# 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_lzh-20211209
_database_code_depnum_ccdc_archive 'CCDC 2191371'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2022-06-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 N2 O3 S'
_chemical_formula_sum            'C11 H12 N2 O3 S'
_chemical_formula_weight         252.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N1 C1 H1'
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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9773(4)
_cell_length_b                   8.6323(4)
_cell_length_c                   8.8553(4)
_cell_angle_alpha                92.357(4)
_cell_angle_beta                 103.812(4)
_cell_angle_gamma                111.690(4)
_cell_volume                     544.55(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3400
_cell_measurement_theta_min      5.1910
_shelx_estimated_absorpt_T_max   0.503
_shelx_estimated_absorpt_T_min   0.503
_exptl_absorpt_coefficient_mu    2.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3648
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.162
_diffrn_reflns_theta_min         5.197
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00 -10.00   1.00    1.00    --  -35.62  86.00 -41.00   27
  2  ω    -12.00  67.00   1.00    1.00    --   35.62 -86.00-160.00   79
  3  ω     99.00 159.00   1.00    1.00    --  107.12  86.00 -41.00   60
  4  ω     88.00 131.00   1.00    1.00    --  107.12 -86.00-160.00   43
  5  ω    -62.00  -3.00   1.00    1.00    --  -35.62  77.00 120.00   59
  6  ω      5.00  32.00   1.00    1.00    --  -35.62  77.00 120.00   27
  7  ω   -102.00 -18.00   1.00    1.00    --  -35.62 -38.00 -30.00   84
  8  ω    -83.00 -41.00   1.00    1.00    --  -35.62-178.00 150.00   42
  9  ω    -41.00  34.00   1.00    1.00    --  -35.62  38.00 120.00   75
 10  ω      1.00  49.00   1.00    1.00    --   35.62 -99.00 -30.00   48
 11  ω     42.00  71.00   1.00    1.00    --   35.62 -99.00   0.00   29
 12  ω     94.00 172.00   1.00    1.00    --  107.12  61.00   0.00   78
 13  ω     84.00 110.00   1.00    1.00    --  107.12 -95.00  30.00   26
 14  ω     81.00 175.00   1.00    1.00    --  107.12  77.00 120.00   94
 15  ω    125.00 153.00   1.00    1.00    --  107.12 111.00 -90.00   28
 16  ω     41.00 112.00   1.00    1.00    --  107.12-111.00   0.00   71
 17  ω     51.00 123.00   1.00    1.00    --  107.12 -61.00 150.00   72
 18  ω    100.00 130.00   1.00    1.00    --  107.12 111.00-150.00   30
 19  ω     40.00  71.00   1.00    1.00    --  107.12 -95.00  30.00   31
 20  ω    117.00 169.00   1.00    1.00    --  107.12  45.00-180.00   52
 21  ω     40.00 108.00   1.00    1.00    --  107.12 -95.00 150.00   68
 22  ω     85.00 129.00   1.00    1.00    --  107.12 -30.00-180.00   44
 23  ω    138.00 169.00   1.00    1.00    --  107.12 111.00-150.00   31
 24  ω    100.00 135.00   1.00    1.00    --  107.12 111.00  60.00   35
 25  ω    102.00 171.00   1.00    1.00    --  107.12 111.00-180.00   69
 26  ω     82.00 174.00   1.00    1.00    --  107.12  77.00-120.00   92
;
_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      -0.0062231000
_diffrn_orient_matrix_UB_12      -0.1791346000
_diffrn_orient_matrix_UB_13      -0.0316945000
_diffrn_orient_matrix_UB_21      -0.1438541000
_diffrn_orient_matrix_UB_22      -0.0293738000
_diffrn_orient_matrix_UB_23      -0.1602813000
_diffrn_orient_matrix_UB_31      0.1611052000
_diffrn_orient_matrix_UB_32      0.0686333000
_diffrn_orient_matrix_UB_33      -0.0779374000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1969
_reflns_number_total             2064
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2064
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+0.2422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S3 S 0.15343(6) 0.25190(5) 0.71015(5) 0.0310(2) Uani 1 1 d . . . . .
O4 O -0.00034(18) 0.25106(17) 0.55365(16) 0.0347(3) Uani 1 1 d . . . . .
O16 O 0.2539(2) 0.15950(19) 0.6652(2) 0.0464(4) Uani 1 1 d . . . . .
O17 O 0.0479(2) 0.1879(2) 0.81750(19) 0.0478(4) Uani 1 1 d . . . . .
N11 N 0.4488(2) 0.70204(19) 0.71721(18) 0.0290(4) Uani 1 1 d . . . . .
N2 N 0.2823(2) 0.4449(2) 0.76578(19) 0.0333(4) Uani 1 1 d . . . . .
C1 C 0.3275(2) 0.5457(2) 0.6595(2) 0.0264(4) Uani 1 1 d . . . . .
C5 C 0.0783(3) 0.3381(2) 0.4424(2) 0.0293(4) Uani 1 1 d . . . . .
C10 C 0.2422(3) 0.4858(2) 0.4887(2) 0.0267(4) Uani 1 1 d . . . . .
C9 C 0.3144(3) 0.5608(3) 0.3682(2) 0.0337(4) Uani 1 1 d . . . . .
H9 H 0.425924 0.655777 0.393620 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5875(3) 0.9987(2) 0.7670(3) 0.0377(5) Uani 1 1 d . . . . .
H14A H 0.682945 1.094668 0.742399 0.045 Uiso 1 1 calc R U . . .
H14B H 0.490400 1.032357 0.786722 0.045 Uiso 1 1 calc R U . . .
C15 C 0.5060(3) 0.8509(2) 0.6351(2) 0.0338(4) Uani 1 1 d . . . . .
H15A H 0.399024 0.855290 0.558218 0.041 Uiso 1 1 calc R U . . .
H15B H 0.599371 0.849756 0.582639 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5288(3) 0.7501(2) 0.8891(2) 0.0353(5) Uani 1 1 d . . . . .
H12A H 0.588688 0.676549 0.933381 0.042 Uiso 1 1 calc R U . . .
H12B H 0.432694 0.745968 0.940164 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2223(3) 0.4957(3) 0.2124(3) 0.0424(5) Uani 1 1 d . . . . .
H8 H 0.271425 0.548405 0.134059 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6713(3) 0.9289(3) 0.9064(2) 0.0389(5) Uani 1 1 d . . . . .
H13A H 0.792158 0.930035 0.902423 0.047 Uiso 1 1 calc R U . . .
H13B H 0.686366 0.993344 1.004621 0.047 Uiso 1 1 calc R U . . .
C6 C -0.0137(3) 0.2719(3) 0.2869(3) 0.0399(5) Uani 1 1 d . . . . .
H6 H -0.122306 0.174012 0.260327 0.048 Uiso 1 1 calc R U . . .
C7 C 0.0576(4) 0.3528(3) 0.1716(3) 0.0464(6) Uani 1 1 d . . . . .
H7 H -0.004885 0.311448 0.066295 0.056 Uiso 1 1 calc R U . . .


_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
S3 O4 1.6144(14) . ?
S3 O16 1.4265(16) . ?
S3 O17 1.4141(15) . ?
S3 N2 1.5808(17) . ?
O4 C5 1.392(2) . ?
N11 C1 1.327(2) . ?
N11 C15 1.480(2) . ?
N11 C12 1.478(2) . ?
N2 C1 1.331(2) . ?
C1 C10 1.484(3) . ?
C5 C10 1.405(3) . ?
C5 C6 1.380(3) . ?
C10 C9 1.401(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.381(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.522(3) . ?
C14 C13 1.517(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.516(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.385(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.377(3) . ?
C7 H7 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
O16 S3 O4 107.22(9) . . ?
O16 S3 N2 111.99(9) . . ?
O17 S3 O4 104.33(9) . . ?
O17 S3 O16 117.65(10) . . ?
O17 S3 N2 110.36(10) . . ?
N2 S3 O4 104.02(8) . . ?
C5 O4 S3 113.48(11) . . ?
C1 N11 C15 129.24(16) . . ?
C1 N11 C12 119.52(15) . . ?
C12 N11 C15 110.85(15) . . ?
C1 N2 S3 119.60(14) . . ?
N11 C1 N2 115.43(16) . . ?
N11 C1 C10 123.17(16) . . ?
N2 C1 C10 121.38(16) . . ?
O4 C5 C10 120.79(16) . . ?
C6 C5 O4 116.49(17) . . ?
C6 C5 C10 122.72(18) . . ?
C5 C10 C1 117.78(16) . . ?
C9 C10 C1 125.68(17) . . ?
C9 C10 C5 116.51(17) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 C10 121.00(19) . . ?
C8 C9 H9 119.5 . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
C13 C14 C15 103.11(16) . . ?
N11 C15 C14 103.47(16) . . ?
N11 C15 H15A 111.1 . . ?
N11 C15 H15B 111.1 . . ?
C14 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.0 . . ?
N11 C12 H12A 111.0 . . ?
N11 C12 H12B 111.0 . . ?
N11 C12 C13 103.58(15) . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.60(19) . . ?
C7 C8 H8 119.7 . . ?
C14 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
C12 C13 C14 103.67(17) . . ?
C12 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 H6 120.5 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S3 O4 C5 C10 -36.4(2) . . . . ?
S3 O4 C5 C6 143.84(16) . . . . ?
S3 N2 C1 N11 -174.46(13) . . . . ?
S3 N2 C1 C10 7.1(2) . . . . ?
O4 S3 N2 C1 -39.33(17) . . . . ?
O4 C5 C10 C1 -0.3(2) . . . . ?
O4 C5 C10 C9 177.68(16) . . . . ?
O4 C5 C6 C7 179.95(18) . . . . ?
O16 S3 O4 C5 -65.55(14) . . . . ?
O16 S3 N2 C1 76.14(17) . . . . ?
O17 S3 O4 C5 168.95(13) . . . . ?
O17 S3 N2 C1 -150.73(16) . . . . ?
N11 C1 C10 C5 -161.44(16) . . . . ?
N11 C1 C10 C9 20.8(3) . . . . ?
N11 C12 C13 C14 31.5(2) . . . . ?
N2 S3 O4 C5 53.23(14) . . . . ?
N2 C1 C10 C5 16.9(3) . . . . ?
N2 C1 C10 C9 -160.91(18) . . . . ?
C1 N11 C15 C14 159.94(18) . . . . ?
C1 N11 C12 C13 174.86(16) . . . . ?
C1 C10 C9 C8 -179.21(18) . . . . ?
C5 C10 C9 C8 3.0(3) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C10 C9 C8 C7 -1.0(3) . . . . ?
C9 C8 C7 C6 -1.5(3) . . . . ?
C15 N11 C1 N2 -169.67(18) . . . . ?
C15 N11 C1 C10 8.7(3) . . . . ?
C15 N11 C12 C13 -11.7(2) . . . . ?
C15 C14 C13 C12 -39.6(2) . . . . ?
C12 N11 C1 N2 2.5(2) . . . . ?
C12 N11 C1 C10 -179.14(17) . . . . ?
C12 N11 C15 C14 -12.7(2) . . . . ?
C13 C14 C15 N11 31.9(2) . . . . ?
C6 C5 C10 C1 179.40(18) . . . . ?
C6 C5 C10 C9 -2.6(3) . . . . ?

_olex2_date_sample_data_collection 2021-12-09
_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 2.268
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_3-68
_database_code_depnum_ccdc_archive 'CCDC 2202654'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-08-21 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2022-08-13
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 N2 O3 S'
_chemical_formula_sum            'C11 H12 N2 O3 S'
_chemical_formula_weight         252.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0147(2)
_cell_length_b                   8.1452(2)
_cell_length_c                   9.4761(2)
_cell_angle_alpha                94.600(2)
_cell_angle_beta                 107.839(2)
_cell_angle_gamma                107.022(2)
_cell_volume                     553.18(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5974
_cell_measurement_temperature    295.12(10)
_cell_measurement_theta_max      75.1220
_cell_measurement_theta_min      4.9700
_shelx_estimated_absorpt_T_max   0.799
_shelx_estimated_absorpt_T_min   0.711
_exptl_absorpt_coefficient_mu    2.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7331
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.431
_diffrn_reflns_theta_min         4.991
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.12(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    102.00 152.00   0.50    0.20    --  109.26  61.00-150.00  100
  2  ω     90.00 124.00   0.50    0.20    --  109.26 137.00 -60.00   68
  3  ω     98.00 178.00   0.50    0.20    --  109.26 125.00 -30.00  160
  4  ω     89.00 177.00   0.50    0.20    --  109.26  30.00 -90.00  176
  5  ω     95.00 150.00   0.50    0.20    --  109.26 125.00  90.00  110
  6  ω     91.00 178.00   0.50    0.20    --  109.26 132.00 122.00  174
  7  ω    -42.00  34.00   0.50    0.05    --  -43.18  37.00 -60.00  152
  8  ω    -51.00 -14.00   0.50    0.20    --  -90.25  45.00-180.00   74
  9  ω    -27.00  38.00   0.50    0.05    --  -43.18  19.00-120.00  130
 10  ω    -27.00  38.00   0.50    0.05    --  -43.18  19.00   0.00  130
 11  ω    -51.00 -14.00   0.50    0.20    --  -90.25  45.00 150.00   74
 12  ω    -51.00 -14.00   0.50    0.20    --  -90.25  45.00  90.00   74
 13  ω    -51.00 -14.00   0.50    0.20    --  -90.25  45.00  60.00   74
 14  ω    -51.00 -14.00   0.50    0.20    --  -90.25  45.00 -90.00   74
 15  ω    -51.00 -14.00   0.50    0.20    --  -90.25  45.00-150.00   74
 16  ω    -86.00 -13.00   0.50    0.05    --  -43.18 125.00-150.00  146
 17  ω    -94.00 -19.00   0.50    0.05    --  -43.18 137.00 -60.00  150
 18  ω    -91.00 -17.00   0.50    0.05    --  -43.18 132.00 122.00  148
 19  ω   -164.00 -67.00   0.50    0.20    --  -90.25 -61.00 -30.00  194
 20  ω   -158.00 -66.00   0.50    0.20    --  -90.25-137.00-123.00  184
 21  ω   -164.00 -67.00   0.50    0.20    --  -90.25 -61.00 -60.00  194
 22  ω   -162.00 -69.00   0.50    0.20    --  -90.25-132.00  52.00  186
 23  ω   -117.00 -69.00   0.50    0.05    --  -43.18-132.00  52.00   96
 24  ω   -117.00 -66.00   0.50    0.05    --  -43.18-137.00-123.00  102
 25  ω     42.00  68.00   0.50    0.20    --  109.26 -61.00  90.00   52
 26  ω     37.00  68.00   0.50    0.20    --  109.26 -61.00 120.00   62
 27  ω     38.00  68.00   0.50    0.20    --  109.26 -61.00  60.00   60
 28  ω     42.00  69.00   0.50    0.20    --  109.26 -61.00  30.00   54
 29  ω     35.00  67.00   0.50    0.20    --  109.26 -61.00 -90.00   64
 30  ω     38.00  65.00   0.50    0.20    --  109.26 -61.00-150.00   54
 31  ω     41.00 104.00   0.50    0.05    --   43.18-137.00-123.00  126
 32  ω     41.00 121.00   0.50    0.20    --  109.26-137.00-123.00  160
 33  ω     36.00 111.00   0.50    0.20    --  109.26-125.00 -60.00  150
 34  ω     47.00  91.00   0.50    0.20    --  109.26 -94.00 -60.00   88
 35  ω     38.00 117.00   0.50    0.20    --  109.26-132.00  52.00  158
 36  ω     43.00 107.00   0.50    0.20    --  109.26-125.00  60.00  128
 37  ω     54.00  80.00   0.50    0.20    --  109.26 -94.00  90.00   52
 38  ω     74.00 108.00   0.50    0.20    --  109.26-125.00 150.00   68
 39  ω     38.00 101.00   0.50    0.05    --   43.18-132.00  52.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2031317000
_diffrn_orient_matrix_UB_12      0.0738710000
_diffrn_orient_matrix_UB_13      0.0067324000
_diffrn_orient_matrix_UB_21      0.0665853000
_diffrn_orient_matrix_UB_22      0.0315769000
_diffrn_orient_matrix_UB_23      0.1736823000
_diffrn_orient_matrix_UB_31      0.0145285000
_diffrn_orient_matrix_UB_32      -0.1846176000
_diffrn_orient_matrix_UB_33      -0.0029828000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2054
_reflns_number_total             2163
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.253
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²+0.1371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1203
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C5-H5
 0.84 with sigma of 0.01
 C7-C8
 2.8 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.26401(6) 0.23982(5) 0.59370(4) 0.0392(2) Uani 1 1 d . . . . .
O1 O 0.1266(2) 0.13810(17) 0.64894(16) 0.0538(4) Uani 1 1 d . . . . .
O2 O 0.3681(2) 0.14837(19) 0.54115(18) 0.0559(4) Uani 1 1 d . . . . .
O3 O 0.73985(19) 1.02309(17) 0.96498(15) 0.0492(4) Uani 1 1 d . . . . .
N1 N 0.4004(2) 0.4124(2) 0.71943(18) 0.0450(4) Uani 1 1 d . . . . .
N2 N 0.4838(2) 0.70958(18) 0.76599(16) 0.0402(4) Uani 1 1 d . . . . .
C1 C 0.1694(2) 0.3508(2) 0.45620(19) 0.0336(4) Uani 1 1 d . . . . .
C2 C 0.0390(2) 0.2795(2) 0.3140(2) 0.0384(4) Uani 1 1 d . . . . .
H2 H -0.012920 0.159065 0.280909 0.046 Uiso 1 1 calc R U . . .
C3 C -0.0116(3) 0.3929(2) 0.2227(2) 0.0420(4) Uani 1 1 d . . . . .
H3 H -0.097474 0.349293 0.125467 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0653(3) 0.5718(3) 0.2755(2) 0.0435(4) Uani 1 1 d . . . . .
H4 H 0.029027 0.646596 0.212782 0.052 Uiso 1 1 calc R U . . .
C5 C 0.1956(3) 0.6425(2) 0.4200(2) 0.0395(4) Uani 1 1 d D . . . .
H5 H 0.244982 0.762842 0.453611 0.047 Uiso 1 1 calc DR U . . .
C6 C 0.2506(2) 0.5303(2) 0.51327(18) 0.0319(4) Uani 1 1 d . . . . .
C7 C 0.3843(2) 0.5556(2) 0.67182(19) 0.0349(4) Uani 1 1 d D . . . .
C8 C 0.4656(3) 0.8805(2) 0.7433(2) 0.0513(5) Uani 1 1 d D . . . .
H8A H 0.380988 0.903516 0.790394 0.062 Uiso 1 1 calc R U . . .
H8B H 0.414073 0.879536 0.636148 0.062 Uiso 1 1 calc R U . . .
C9 C 0.6518(3) 1.0220(2) 0.8103(2) 0.0502(5) Uani 1 1 d . . . . .
H9A H 0.731174 1.005526 0.754955 0.060 Uiso 1 1 calc R U . . .
H9B H 0.635801 1.134396 0.799340 0.060 Uiso 1 1 calc R U . . .
C10 C 0.7702(3) 0.8612(3) 0.9802(2) 0.0509(5) Uani 1 1 d . . . . .
H10A H 0.833765 0.862979 1.085757 0.061 Uiso 1 1 calc R U . . .
H10B H 0.849748 0.846005 0.924703 0.061 Uiso 1 1 calc R U . . .
C11 C 0.5910(3) 0.7098(3) 0.9227(2) 0.0549(6) Uani 1 1 d . . . . .
H11A H 0.617726 0.601266 0.928018 0.066 Uiso 1 1 calc R U . . .
H11B H 0.517593 0.716936 0.986077 0.066 Uiso 1 1 calc R U . . .


_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
S1 O1 1.4359(15) . ?
S1 O2 1.4345(15) . ?
S1 N1 1.6199(16) . ?
S1 C1 1.7534(17) . ?
O3 C9 1.417(2) . ?
O3 C10 1.419(3) . ?
N1 C7 1.311(2) . ?
N2 C7 1.343(2) . ?
N2 C8 1.467(2) . ?
N2 C11 1.470(2) . ?
C1 C2 1.379(2) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(2) . ?
C6 C7 1.511(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.501(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.502(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 109.59(9) . . ?
O1 S1 C1 111.71(9) . . ?
O2 S1 O1 116.02(9) . . ?
O2 S1 N1 111.27(10) . . ?
O2 S1 C1 110.17(8) . . ?
N1 S1 C1 96.36(8) . . ?
C9 O3 C10 109.10(14) . . ?
C7 N1 S1 111.50(12) . . ?
C7 N2 C8 126.81(15) . . ?
C7 N2 C11 118.72(15) . . ?
C8 N2 C11 112.81(15) . . ?
C2 C1 S1 127.66(13) . . ?
C2 C1 C6 123.91(16) . . ?
C6 C1 S1 108.43(12) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.64(16) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.15(16) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.74(17) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.04(16) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 107.96(14) . . ?
C5 C6 C1 117.51(15) . . ?
C5 C6 C7 134.53(15) . . ?
N1 C7 N2 118.51(15) . . ?
N1 C7 C6 115.72(14) . . ?
N2 C7 C6 125.76(14) . . ?
N2 C8 H8A 109.6 . . ?
N2 C8 H8B 109.6 . . ?
N2 C8 C9 110.39(17) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
O3 C9 C8 112.35(17) . . ?
O3 C9 H9A 109.1 . . ?
O3 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
O3 C10 H10A 109.2 . . ?
O3 C10 H10B 109.2 . . ?
O3 C10 C11 111.84(18) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
N2 C11 C10 110.99(16) . . ?
N2 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C7 N2 177.51(13) . . . . ?
S1 N1 C7 C6 -1.7(2) . . . . ?
S1 C1 C2 C3 -178.17(14) . . . . ?
S1 C1 C6 C5 179.22(12) . . . . ?
S1 C1 C6 C7 -1.13(16) . . . . ?
O1 S1 N1 C7 -114.91(15) . . . . ?
O1 S1 C1 C2 -66.47(18) . . . . ?
O1 S1 C1 C6 114.31(12) . . . . ?
O2 S1 N1 C7 115.42(15) . . . . ?
O2 S1 C1 C2 64.02(18) . . . . ?
O2 S1 C1 C6 -115.20(13) . . . . ?
O3 C10 C11 N2 54.9(3) . . . . ?
N1 S1 C1 C2 179.48(17) . . . . ?
N1 S1 C1 C6 0.26(14) . . . . ?
N2 C8 C9 O3 -55.5(2) . . . . ?
C1 S1 N1 C7 0.85(16) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C6 C7 N1 1.9(2) . . . . ?
C1 C6 C7 N2 -177.28(17) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 179.62(16) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 179.82(18) . . . . ?
C5 C6 C7 N1 -178.55(19) . . . . ?
C5 C6 C7 N2 2.3(3) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 N2 C8 C9 -146.00(19) . . . . ?
C7 N2 C11 C10 144.63(19) . . . . ?
C8 N2 C7 N1 -170.39(19) . . . . ?
C8 N2 C7 C6 8.7(3) . . . . ?
C8 N2 C11 C10 -49.0(3) . . . . ?
C9 O3 C10 C11 -60.6(2) . . . . ?
C10 O3 C9 C8 61.2(2) . . . . ?
C11 N2 C7 N1 -6.2(3) . . . . ?
C11 N2 C7 C6 172.95(17) . . . . ?
C11 N2 C8 C9 49.0(3) . . . . ?

# end Validation Reply Form
_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 2.506
_oxdiff_exptl_absorpt_empirical_full_min 0.490
# start Validation Reply Form
_vrf_PLAT410_3-68                
;
PROBLEM: Short Intra H...H Contact  H5       ..H8B      .       1.81 Ang.  
RESPONSE: It is obviously observed that the 
                    distance of H5 and H8B is short in
                      the the crystal structure.
;
####################################################################### 
# 
# 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_lzh-20220311
_database_code_depnum_ccdc_archive 'CCDC 2191370'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2022-06-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N2 O3 S'
_chemical_formula_sum            'C15 H14 N2 O3 S'
_chemical_formula_weight         302.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N1 O1 C1'
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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8870(2)
_cell_length_b                   7.8158(2)
_cell_length_c                   18.9459(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.306(2)
_cell_angle_gamma                90
_cell_volume                     1435.63(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3561
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4210
_cell_measurement_theta_min      4.5630
_shelx_estimated_absorpt_T_max   0.677
_shelx_estimated_absorpt_T_min   0.570
_exptl_absorpt_coefficient_mu    2.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6295
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.484
_diffrn_reflns_theta_min         4.561
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  34.00   1.00    2.07    --  -35.62  33.00  99.00   90
  2  ω   -105.00 -15.00   1.00    2.07    --  -35.62 -33.00 -58.00   90
  3  ω     15.00 100.00   1.00    2.07    --   35.62  33.00  99.00   85
  4  ω    143.00 169.00   1.00    8.28    --  107.12  33.00  99.00   26
  5  ω     97.00 140.00   1.00    8.28    --  107.12  33.00  99.00   43
  6  ω     54.00 119.00   1.00    8.28    --  107.12 -33.00 -58.00   65
  7  ω     74.00 105.00   1.00    2.07    --   35.62 178.00-120.00   31
  8  ω     22.00 103.00   1.00    2.07    --   35.62  57.00-150.00   81
  9  ω    -13.00  12.00   1.00    2.07    --   35.62 -33.00 -58.00   25
 10  ω     20.00 103.00   1.00    2.07    --   35.62  57.00 120.00   83
 11  ω     57.00  89.00   1.00    8.28    --  107.12 178.00   0.00   32
 12  ω    117.00 143.00   1.00    8.28    --  107.12 178.00   0.00   26
 13  ω     38.00  81.00   1.00    8.28    --  107.12 -95.00  60.00   43
 14  ω     93.00 176.00   1.00    8.28    --  107.12  30.00 150.00   83
 15  ω    102.00 177.00   1.00    8.28    --  107.12 111.00 -30.00   75
 16  ω     42.00  94.00   1.00    8.28    --  107.12 -95.00  90.00   52
 17  ω    101.00 127.00   1.00    8.28    --  107.12  61.00 -30.00   26
 18  ω    129.00 155.00   1.00    8.28    --  107.12  61.00 -30.00   26
 19  ω     37.00 102.00   1.00    8.28    --  107.12-111.00 -60.00   65
;
_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      0.1143044000
_diffrn_orient_matrix_UB_12      -0.0773124000
_diffrn_orient_matrix_UB_13      0.0582891000
_diffrn_orient_matrix_UB_21      0.0897348000
_diffrn_orient_matrix_UB_22      -0.0293182000
_diffrn_orient_matrix_UB_23      -0.0568385000
_diffrn_orient_matrix_UB_31      0.0641666000
_diffrn_orient_matrix_UB_32      0.1789106000
_diffrn_orient_matrix_UB_33      0.0158971000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2421
_reflns_number_total             2745
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2745
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1139P)²+0.0645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1601
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C9(H9), C21(H21), C20(H20), C6(H6), C18(H18), C19(H19), C8(H8),
 C7(H7)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S3 S 0.31393(5) 0.69761(7) 0.54434(2) 0.0510(2) Uani 1 1 d . . . . .
O4 O 0.46080(15) 0.71851(19) 0.51987(8) 0.0509(4) Uani 1 1 d . . . . .
O14 O 0.23594(18) 0.8495(2) 0.52293(11) 0.0670(5) Uani 1 1 d . . . . .
N11 N 0.20996(17) 0.3648(2) 0.40252(8) 0.0459(4) Uani 1 1 d . . . . .
N2 N 0.24715(18) 0.5328(2) 0.50161(8) 0.0489(4) Uani 1 1 d . . . . .
O15 O 0.3517(2) 0.6592(3) 0.61863(9) 0.0795(6) Uani 1 1 d . . . . .
C16 C 0.17417(18) 0.2712(2) 0.27315(10) 0.0391(4) Uani 1 1 d . . . . .
C10 C 0.35322(18) 0.6213(2) 0.40114(10) 0.0404(4) Uani 1 1 d . . . . .
C1 C 0.26868(18) 0.5039(2) 0.43619(9) 0.0403(4) Uani 1 1 d . . . . .
C5 C 0.44791(19) 0.7273(2) 0.44536(11) 0.0439(4) Uani 1 1 d . . . . .
C17 C 0.2180(2) 0.1800(3) 0.21908(11) 0.0461(4) Uani 1 1 d . . . . .
H17 H 0.299007 0.116574 0.229743 0.055 Uiso 1 1 calc R U . . .
C13 C 0.2660(2) 0.2730(3) 0.34747(10) 0.0461(4) Uani 1 1 d . . . . .
H13A H 0.284042 0.155663 0.363224 0.055 Uiso 1 1 calc R U . . .
H13B H 0.353654 0.324376 0.343768 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3373(2) 0.6453(3) 0.32703(10) 0.0472(4) Uani 1 1 d . . . . .
H9 H 0.272242 0.581184 0.295848 0.057 Uiso 1 1 calc R U . . .
C21 C 0.0504(2) 0.3598(3) 0.25702(11) 0.0489(5) Uani 1 1 d . . . . .
H21 H 0.018597 0.419768 0.292905 0.059 Uiso 1 1 calc R U . . .
C20 C -0.0257(2) 0.3587(3) 0.18743(13) 0.0546(5) Uani 1 1 d . . . . .
H20 H -0.109064 0.417382 0.177031 0.065 Uiso 1 1 calc R U . . .
C6 C 0.5296(2) 0.8427(3) 0.41839(14) 0.0549(5) Uani 1 1 d . . . . .
H6 H 0.594057 0.908352 0.449257 0.066 Uiso 1 1 calc R U . . .
C18 C 0.1424(2) 0.1823(3) 0.14933(11) 0.0555(5) Uani 1 1 d . . . . .
H18 H 0.174061 0.123178 0.113151 0.067 Uiso 1 1 calc R U . . .
C19 C 0.0201(3) 0.2724(3) 0.13355(11) 0.0560(5) Uani 1 1 d . . . . .
H19 H -0.030826 0.274674 0.086763 0.067 Uiso 1 1 calc R U . . .
C8 C 0.4173(3) 0.7632(3) 0.29939(13) 0.0583(5) Uani 1 1 d . . . . .
H8 H 0.405601 0.777969 0.249855 0.070 Uiso 1 1 calc R U . . .
C7 C 0.5145(3) 0.8594(3) 0.34505(15) 0.0615(6) Uani 1 1 d . . . . .
H7 H 0.570030 0.935834 0.326028 0.074 Uiso 1 1 calc R U . . .
C12 C 0.1115(3) 0.2684(3) 0.43558(13) 0.0629(6) Uani 1 1 d . . . . .
H12A H 0.160759 0.200550 0.474512 0.094 Uiso 1 1 calc R U . . .
H12B H 0.057722 0.194919 0.400243 0.094 Uiso 1 1 calc R U . . .
H12C H 0.051574 0.346619 0.453654 0.094 Uiso 1 1 calc R U . . .


_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
S3 O4 1.6169(16) . ?
S3 O14 1.4302(19) . ?
S3 N2 1.5939(16) . ?
S3 O15 1.4156(18) . ?
O4 C5 1.394(2) . ?
N11 C1 1.334(2) . ?
N11 C13 1.462(3) . ?
N11 C12 1.465(3) . ?
N2 C1 1.317(2) . ?
C16 C17 1.385(3) . ?
C16 C13 1.518(2) . ?
C16 C21 1.387(3) . ?
C10 C1 1.483(2) . ?
C10 C5 1.399(3) . ?
C10 C9 1.395(3) . ?
C5 C6 1.374(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C8 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.384(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.372(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.383(4) . ?
C7 H7 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
O14 S3 O4 107.42(10) . . ?
O14 S3 N2 112.33(10) . . ?
N2 S3 O4 103.99(9) . . ?
O15 S3 O4 103.29(11) . . ?
O15 S3 O14 118.71(13) . . ?
O15 S3 N2 109.64(11) . . ?
C5 O4 S3 112.73(12) . . ?
C1 N11 C13 123.43(16) . . ?
C1 N11 C12 118.55(16) . . ?
C13 N11 C12 115.40(17) . . ?
C1 N2 S3 119.28(14) . . ?
C17 C16 C13 118.27(17) . . ?
C17 C16 C21 118.96(17) . . ?
C21 C16 C13 122.76(17) . . ?
C5 C10 C1 117.90(17) . . ?
C9 C10 C1 124.89(16) . . ?
C9 C10 C5 116.96(17) . . ?
N11 C1 C10 121.36(15) . . ?
N2 C1 N11 116.99(16) . . ?
N2 C1 C10 121.65(17) . . ?
O4 C5 C10 119.66(17) . . ?
C6 C5 O4 117.72(18) . . ?
C6 C5 C10 122.62(19) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.72(19) . . ?
C18 C17 H17 119.6 . . ?
N11 C13 C16 115.13(16) . . ?
N11 C13 H13A 108.5 . . ?
N11 C13 H13B 108.5 . . ?
C16 C13 H13A 108.5 . . ?
C16 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.6 . . ?
C16 C21 H21 120.1 . . ?
C20 C21 C16 119.89(18) . . ?
C20 C21 H21 120.1 . . ?
C21 C20 H20 119.5 . . ?
C19 C20 C21 120.96(19) . . ?
C19 C20 H20 119.5 . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.9(2) . . ?
C7 C6 H6 120.6 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 119.51(19) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.3(2) . . ?
C7 C8 H8 119.8 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S3 O4 C5 C10 -40.2(2) . . . . ?
S3 O4 C5 C6 139.37(17) . . . . ?
S3 N2 C1 N11 -179.65(14) . . . . ?
S3 N2 C1 C10 -0.2(3) . . . . ?
O4 S3 N2 C1 -35.33(18) . . . . ?
O4 C5 C6 C7 -177.10(19) . . . . ?
O14 S3 O4 C5 -64.34(15) . . . . ?
O14 S3 N2 C1 80.51(19) . . . . ?
N2 S3 O4 C5 54.91(15) . . . . ?
O15 S3 O4 C5 169.41(15) . . . . ?
O15 S3 N2 C1 -145.23(18) . . . . ?
C16 C17 C18 C19 -1.8(3) . . . . ?
C16 C21 C20 C19 -0.7(3) . . . . ?
C10 C5 C6 C7 2.4(3) . . . . ?
C10 C9 C8 C7 0.0(3) . . . . ?
C1 N11 C13 C16 -116.9(2) . . . . ?
C1 C10 C5 O4 0.6(3) . . . . ?
C1 C10 C5 C6 -178.88(18) . . . . ?
C1 C10 C9 C8 177.2(2) . . . . ?
C5 C10 C1 N11 -158.59(18) . . . . ?
C5 C10 C1 N2 22.0(3) . . . . ?
C5 C10 C9 C8 3.1(3) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C17 C16 C13 N11 -177.16(17) . . . . ?
C17 C16 C21 C20 -1.3(3) . . . . ?
C17 C18 C19 C20 -0.2(4) . . . . ?
C13 N11 C1 N2 -152.41(19) . . . . ?
C13 N11 C1 C10 28.1(3) . . . . ?
C13 C16 C17 C18 -176.13(19) . . . . ?
C13 C16 C21 C20 177.27(19) . . . . ?
C9 C10 C1 N11 27.4(3) . . . . ?
C9 C10 C1 N2 -152.1(2) . . . . ?
C9 C10 C5 O4 175.15(17) . . . . ?
C9 C10 C5 C6 -4.4(3) . . . . ?
C9 C8 C7 C6 -2.1(4) . . . . ?
C21 C16 C17 C18 2.5(3) . . . . ?
C21 C16 C13 N11 4.3(3) . . . . ?
C21 C20 C19 C18 1.4(4) . . . . ?
C12 N11 C1 N2 8.4(3) . . . . ?
C12 N11 C1 C10 -171.08(19) . . . . ?
C12 N11 C13 C16 81.8(2) . . . . ?

_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 1.760
_oxdiff_exptl_absorpt_empirical_full_min 0.787
####################################################################### 
# 
# 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_lzh-2-20220531-2
_database_code_depnum_ccdc_archive 'CCDC 2195094'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2022-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N2 O4 S'
_chemical_formula_sum            'C15 H14 N2 O4 S'
_chemical_formula_weight         318.34
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 C1 N1 O1 H1'
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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   11.27050(10)
_cell_length_b                   12.2230(2)
_cell_length_c                   20.2303(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2786.91(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3950
_cell_measurement_theta_min      4.2230
_shelx_estimated_absorpt_T_max   0.660
_shelx_estimated_absorpt_T_min   0.550
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8630
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.385
_diffrn_reflns_theta_min         4.226
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  33.00   1.00    1.00    --  -35.62  85.00 -89.00  100
  2  ω    -16.00  66.00   1.00    1.00    --   35.62 -84.00  44.00   82
  3  ω    133.00 158.00   1.00    1.40    --  107.12  85.00 -89.00   25
  4  ω    149.00 175.00   1.00    1.40    --  107.12  56.00  48.00   26
  5  ω     69.00 131.00   1.00    1.40    --  107.12 -84.00  44.00   62
  6  ω      4.00  34.00   1.00    1.00    --   35.62 -85.00 151.00   30
  7  ω     57.00  99.00   1.00    1.00    --   35.62 178.00-150.00   42
  8  ω     63.00 108.00   1.00    1.00    --   35.62 178.00  60.00   45
  9  ω     58.00  99.00   1.00    1.00    --   35.62 178.00-180.00   41
 10  ω     39.00  88.00   1.00    1.40    --  107.12 -95.00-120.00   49
 11  ω     98.00 166.00   1.00    1.40    --  107.12  61.00  30.00   68
 12  ω     89.00 174.00   1.00    1.40    --  107.12  61.00 150.00   85
 13  ω     39.00  80.00   1.00    1.40    --  107.12 -95.00 -60.00   41
;
_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      0.1025534000
_diffrn_orient_matrix_UB_12      -0.0285802000
_diffrn_orient_matrix_UB_13      -0.0472871000
_diffrn_orient_matrix_UB_21      0.0634250000
_diffrn_orient_matrix_UB_22      0.1072654000
_diffrn_orient_matrix_UB_23      0.0189713000
_diffrn_orient_matrix_UB_31      0.0645165000
_diffrn_orient_matrix_UB_32      -0.0597506000
_diffrn_orient_matrix_UB_33      0.0565219000
_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         0.555
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.708
_reflns_number_gt                4461
_reflns_number_total             4686
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1523 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(8)
_refine_ls_extinction_coef       0.0030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.2399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0896
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C38(H38A,H38B), C20(H20A,H20B), C42(H42A,H42B), C19(H19A,
 H19B), C41(H41A,H41B), C39(H39A,H39B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C2(H2), C3(H3), C13(H13), C14(H14), C11(H11), C33(H33), C36(H36),
 C34(H34), C30(H30), C35(H35), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S6 S 1.02957(6) 0.66234(6) 0.58458(3) 0.03632(18) Uani 1 1 d . . . . .
S27 S 0.46983(6) 0.79302(6) 0.84506(4) 0.03958(19) Uani 1 1 d . . . . .
O5 O 0.98374(17) 0.58496(16) 0.64446(10) 0.0389(5) Uani 1 1 d . . . . .
O22 O 0.99683(18) 0.77160(16) 0.60059(11) 0.0479(5) Uani 1 1 d . . . . .
O28 O 0.51583(18) 0.87106(16) 0.90458(10) 0.0399(5) Uani 1 1 d . . . . .
O44 O 0.50250(19) 0.68392(17) 0.86117(11) 0.0532(6) Uani 1 1 d . . . . .
O18 O 0.6768(2) 0.47387(19) 0.36114(10) 0.0462(5) Uani 1 1 d . . . . .
O40 O 0.8085(2) 1.00509(19) 0.62134(10) 0.0491(6) Uani 1 1 d . . . . .
N15 N 0.7923(2) 0.54535(18) 0.47715(11) 0.0299(5) Uani 1 1 d . . . . .
O21 O 1.15164(19) 0.6375(2) 0.57842(13) 0.0565(6) Uani 1 1 d . . . . .
N37 N 0.7036(2) 0.91485(19) 0.73689(10) 0.0313(5) Uani 1 1 d . . . . .
N7 N 0.9594(2) 0.61548(19) 0.52215(11) 0.0351(5) Uani 1 1 d . . . . .
O43 O 0.34789(19) 0.8179(2) 0.83930(14) 0.0618(7) Uani 1 1 d . . . . .
N26 N 0.5386(2) 0.84010(19) 0.78252(11) 0.0362(5) Uani 1 1 d . . . . .
C9 C 0.7885(2) 0.5910(2) 0.59564(12) 0.0272(5) Uani 1 1 d . . . . .
C4 C 0.8607(3) 0.5867(2) 0.65084(13) 0.0309(6) Uani 1 1 d . . . . .
C1 C 0.6196(2) 0.6066(2) 0.67215(12) 0.0296(6) Uani 1 1 d . . . . .
C8 C 0.8484(2) 0.5842(2) 0.53091(12) 0.0281(5) Uani 1 1 d . . . . .
C31 C 0.8017(3) 0.8726(2) 0.98503(14) 0.0401(7) Uani 1 1 d . . . . .
H31 H 0.832159 0.880938 1.027463 0.048 Uiso 1 1 calc R U . . .
C32 C 0.8798(3) 0.8521(2) 0.93186(14) 0.0346(6) Uani 1 1 d . . . . .
C25 C 0.6499(2) 0.8719(2) 0.79054(13) 0.0296(5) Uani 1 1 d . . . . .
C2 C 0.6989(3) 0.5943(2) 0.72569(12) 0.0365(6) Uani 1 1 d . . . . .
H2 H 0.669195 0.591788 0.768548 0.044 Uiso 1 1 calc R U . . .
C23 C 0.8351(2) 0.8463(2) 0.86593(13) 0.0297(5) Uani 1 1 d . . . . .
C24 C 0.7106(2) 0.8644(2) 0.85539(13) 0.0296(5) Uani 1 1 d . . . . .
C10 C 0.6636(2) 0.60931(19) 0.60608(12) 0.0267(5) Uani 1 1 d . . . . .
C29 C 0.6389(3) 0.8718(2) 0.91063(14) 0.0338(6) Uani 1 1 d . . . . .
C3 C 0.8180(3) 0.5861(3) 0.71573(13) 0.0390(7) Uani 1 1 d . . . . .
H3 H 0.869847 0.580206 0.751313 0.047 Uiso 1 1 calc R U . . .
C13 C 0.4641(3) 0.6485(2) 0.56817(14) 0.0360(6) Uani 1 1 d . . . . .
H13 H 0.412139 0.663584 0.533665 0.043 Uiso 1 1 calc R U . . .
C16 C 0.7099(2) 0.4519(2) 0.47906(13) 0.0314(6) Uani 1 1 d . . . . .
H16A H 0.668717 0.450737 0.521162 0.038 Uiso 1 1 calc R U . . .
H16B H 0.754007 0.384184 0.474718 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5824(2) 0.6353(2) 0.55540(12) 0.0306(5) Uani 1 1 d . . . . .
H14 H 0.609895 0.643651 0.512355 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4966(2) 0.6205(2) 0.68340(13) 0.0354(6) Uani 1 1 d . . . . .
H11 H 0.467528 0.616636 0.726363 0.043 Uiso 1 1 calc R U . . .
C38 C 0.7888(2) 1.0057(2) 0.74047(13) 0.0327(6) Uani 1 1 d . . . . .
H38A H 0.834296 1.000512 0.781060 0.039 Uiso 1 1 calc R U . . .
H38B H 0.746519 1.074826 0.740743 0.039 Uiso 1 1 calc R U . . .
C20 C 0.8473(3) 0.5585(2) 0.41202(13) 0.0372(6) Uani 1 1 d . . . . .
H20A H 0.896903 0.495810 0.402031 0.045 Uiso 1 1 calc R U . . .
H20B H 0.896547 0.623644 0.411391 0.045 Uiso 1 1 calc R U . . .
C33 C 0.9152(2) 0.8175(2) 0.81521(13) 0.0341(6) Uani 1 1 d . . . . .
H33 H 0.887664 0.808947 0.772189 0.041 Uiso 1 1 calc R U . . .
C36 C 1.0025(3) 0.8352(2) 0.94334(16) 0.0435(7) Uani 1 1 d . . . . .
H36 H 1.031911 0.840695 0.986171 0.052 Uiso 1 1 calc R U . . .
C42 C 0.6415(3) 0.9137(3) 0.67321(13) 0.0384(6) Uani 1 1 d . . . . .
H42A H 0.591053 0.977728 0.669682 0.046 Uiso 1 1 calc R U . . .
H42B H 0.591658 0.849182 0.670347 0.046 Uiso 1 1 calc R U . . .
C34 C 1.0336(3) 0.8019(2) 0.82872(16) 0.0434(7) Uani 1 1 d . . . . .
H34 H 1.085347 0.784827 0.794434 0.052 Uiso 1 1 calc R U . . .
C19 C 0.7491(3) 0.5685(3) 0.36146(13) 0.0432(7) Uani 1 1 d . . . . .
H19A H 0.700797 0.631999 0.371552 0.052 Uiso 1 1 calc R U . . .
H19B H 0.783358 0.578858 0.317939 0.052 Uiso 1 1 calc R U . . .
C30 C 0.6830(3) 0.8803(2) 0.97514(14) 0.0410(7) Uani 1 1 d . . . . .
H30 H 0.631704 0.891037 1.010580 0.049 Uiso 1 1 calc R U . . .
C41 C 0.7305(3) 0.9133(3) 0.61732(13) 0.0453(7) Uani 1 1 d . . . . .
H41A H 0.776624 0.846307 0.619035 0.054 Uiso 1 1 calc R U . . .
H41B H 0.688774 0.914948 0.575408 0.054 Uiso 1 1 calc R U . . .
C39 C 0.8720(3) 1.0016(3) 0.68155(15) 0.0426(7) Uani 1 1 d . . . . .
H39A H 0.926231 1.063148 0.683530 0.051 Uiso 1 1 calc R U . . .
H39B H 0.918485 0.934948 0.683383 0.051 Uiso 1 1 calc R U . . .
C35 C 1.0776(3) 0.8112(3) 0.89341(17) 0.0474(8) Uani 1 1 d . . . . .
H35 H 1.157985 0.800873 0.901806 0.057 Uiso 1 1 calc R U . . .
C12 C 0.4204(3) 0.6394(2) 0.63315(15) 0.0385(6) Uani 1 1 d . . . . .
H12 H 0.339598 0.646313 0.641395 0.046 Uiso 1 1 calc R U . . .
C17 C 0.6205(3) 0.4612(3) 0.42329(14) 0.0393(7) Uani 1 1 d . . . . .
H17A H 0.571488 0.395945 0.422474 0.047 Uiso 1 1 calc R U . . .
H17B H 0.569149 0.523439 0.431332 0.047 Uiso 1 1 calc R U . . .


_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
S6 O5 1.621(2) . ?
S6 O22 1.423(2) . ?
S6 O21 1.414(2) . ?
S6 N7 1.596(2) . ?
S27 O28 1.621(2) . ?
S27 O44 1.421(2) . ?
S27 O43 1.412(2) . ?
S27 N26 1.592(2) . ?
O5 C4 1.393(3) . ?
O28 C29 1.392(3) . ?
O18 C19 1.414(4) . ?
O18 C17 1.417(3) . ?
O40 C41 1.428(4) . ?
O40 C39 1.413(4) . ?
N15 C8 1.345(3) . ?
N15 C16 1.472(3) . ?
N15 C20 1.465(3) . ?
N37 C25 1.349(3) . ?
N37 C38 1.470(3) . ?
N37 C42 1.466(3) . ?
N7 C8 1.321(3) . ?
N26 C25 1.323(3) . ?
C9 C4 1.382(3) . ?
C9 C8 1.475(3) . ?
C9 C10 1.441(4) . ?
C4 C3 1.398(4) . ?
C1 C2 1.412(4) . ?
C1 C10 1.426(3) . ?
C1 C11 1.415(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.412(4) . ?
C31 C30 1.357(4) . ?
C32 C23 1.427(4) . ?
C32 C36 1.418(4) . ?
C25 C24 1.483(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.361(4) . ?
C23 C24 1.437(4) . ?
C23 C33 1.411(4) . ?
C24 C29 1.382(4) . ?
C10 C14 1.411(3) . ?
C29 C30 1.400(4) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.367(4) . ?
C13 C12 1.408(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.517(4) . ?
C14 H14 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.350(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.517(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.512(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.375(4) . ?
C36 H36 0.9300 . ?
C36 C35 1.350(4) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C41 1.512(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.404(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C30 H30 0.9300 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C35 H35 0.9300 . ?
C12 H12 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O22 S6 O5 107.14(12) . . ?
O22 S6 N7 112.86(13) . . ?
O21 S6 O5 104.51(13) . . ?
O21 S6 O22 118.27(14) . . ?
O21 S6 N7 109.58(14) . . ?
N7 S6 O5 102.95(11) . . ?
O44 S27 O28 107.40(13) . . ?
O44 S27 N26 113.28(14) . . ?
O43 S27 O28 104.24(14) . . ?
O43 S27 O44 118.21(15) . . ?
O43 S27 N26 109.30(15) . . ?
N26 S27 O28 102.82(12) . . ?
C4 O5 S6 112.18(16) . . ?
C29 O28 S27 112.80(17) . . ?
C19 O18 C17 110.1(2) . . ?
C39 O40 C41 109.7(2) . . ?
C8 N15 C16 123.3(2) . . ?
C8 N15 C20 119.3(2) . . ?
C20 N15 C16 112.1(2) . . ?
C25 N37 C38 123.2(2) . . ?
C25 N37 C42 119.2(2) . . ?
C42 N37 C38 111.2(2) . . ?
C8 N7 S6 117.85(19) . . ?
C25 N26 S27 118.1(2) . . ?
C4 C9 C8 116.5(2) . . ?
C4 C9 C10 117.5(2) . . ?
C10 C9 C8 125.8(2) . . ?
O5 C4 C3 115.4(2) . . ?
C9 C4 O5 120.8(2) . . ?
C9 C4 C3 123.8(3) . . ?
C2 C1 C10 120.0(2) . . ?
C2 C1 C11 120.6(2) . . ?
C11 C1 C10 119.3(2) . . ?
N15 C8 C9 121.5(2) . . ?
N7 C8 N15 116.1(2) . . ?
N7 C8 C9 122.4(2) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C30 C31 C32 121.0(3) . . ?
C31 C32 C23 120.1(3) . . ?
C31 C32 C36 120.6(3) . . ?
C36 C32 C23 119.3(3) . . ?
N37 C25 C24 121.9(2) . . ?
N26 C25 N37 116.2(2) . . ?
N26 C25 C24 121.9(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C32 C23 C24 118.4(2) . . ?
C33 C23 C32 117.8(2) . . ?
C33 C23 C24 123.7(2) . . ?
C23 C24 C25 126.3(2) . . ?
C29 C24 C25 116.2(2) . . ?
C29 C24 C23 117.5(2) . . ?
C1 C10 C9 118.3(2) . . ?
C14 C10 C9 124.2(2) . . ?
C14 C10 C1 117.4(2) . . ?
O28 C29 C30 115.8(2) . . ?
C24 C29 O28 120.7(3) . . ?
C24 C29 C30 123.4(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 H3 120.7 . . ?
C14 C13 H13 119.7 . . ?
C14 C13 C12 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
N15 C16 H16A 109.7 . . ?
N15 C16 H16B 109.7 . . ?
N15 C16 C17 110.0(2) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C10 C14 H14 119.3 . . ?
C13 C14 C10 121.5(2) . . ?
C13 C14 H14 119.3 . . ?
C1 C11 H11 119.3 . . ?
C12 C11 C1 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
N37 C38 H38A 109.7 . . ?
N37 C38 H38B 109.7 . . ?
N37 C38 C39 109.9(2) . . ?
H38A C38 H38B 108.2 . . ?
C39 C38 H38A 109.7 . . ?
C39 C38 H38B 109.7 . . ?
N15 C20 H20A 110.1 . . ?
N15 C20 H20B 110.1 . . ?
N15 C20 C19 107.9(2) . . ?
H20A C20 H20B 108.4 . . ?
C19 C20 H20A 110.1 . . ?
C19 C20 H20B 110.1 . . ?
C23 C33 H33 119.6 . . ?
C34 C33 C23 120.7(3) . . ?
C34 C33 H33 119.6 . . ?
C32 C36 H36 119.3 . . ?
C35 C36 C32 121.4(3) . . ?
C35 C36 H36 119.3 . . ?
N37 C42 H42A 109.7 . . ?
N37 C42 H42B 109.7 . . ?
N37 C42 C41 109.9(2) . . ?
H42A C42 H42B 108.2 . . ?
C41 C42 H42A 109.7 . . ?
C41 C42 H42B 109.7 . . ?
C33 C34 H34 119.4 . . ?
C33 C34 C35 121.1(3) . . ?
C35 C34 H34 119.4 . . ?
O18 C19 C20 111.1(2) . . ?
O18 C19 H19A 109.4 . . ?
O18 C19 H19B 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C31 C30 C29 118.8(3) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
O40 C41 C42 111.3(2) . . ?
O40 C41 H41A 109.4 . . ?
O40 C41 H41B 109.4 . . ?
C42 C41 H41A 109.4 . . ?
C42 C41 H41B 109.4 . . ?
H41A C41 H41B 108.0 . . ?
O40 C39 C38 111.3(2) . . ?
O40 C39 H39A 109.4 . . ?
O40 C39 H39B 109.4 . . ?
C38 C39 H39A 109.4 . . ?
C38 C39 H39B 109.4 . . ?
H39A C39 H39B 108.0 . . ?
C36 C35 C34 119.6(3) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C13 C12 H12 120.2 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
O18 C17 C16 111.8(2) . . ?
O18 C17 H17A 109.3 . . ?
O18 C17 H17B 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S6 O5 C4 C9 37.5(3) . . . . ?
S6 O5 C4 C3 -141.2(2) . . . . ?
S6 N7 C8 N15 179.92(19) . . . . ?
S6 N7 C8 C9 -0.1(3) . . . . ?
S27 O28 C29 C24 34.9(3) . . . . ?
S27 O28 C29 C30 -145.1(2) . . . . ?
S27 N26 C25 N37 -177.74(19) . . . . ?
S27 N26 C25 C24 0.1(3) . . . . ?
O5 S6 N7 C8 38.4(2) . . . . ?
O5 C4 C3 C2 176.1(2) . . . . ?
O22 S6 O5 C4 62.8(2) . . . . ?
O22 S6 N7 C8 -76.8(2) . . . . ?
O28 S27 N26 C25 38.7(2) . . . . ?
O28 C29 C30 C31 174.7(3) . . . . ?
O44 S27 O28 C29 63.8(2) . . . . ?
O44 S27 N26 C25 -76.9(2) . . . . ?
N15 C16 C17 O18 53.6(3) . . . . ?
N15 C20 C19 O18 -60.3(3) . . . . ?
O21 S6 O5 C4 -170.9(2) . . . . ?
O21 S6 N7 C8 149.1(2) . . . . ?
N37 C25 C24 C23 -33.3(4) . . . . ?
N37 C25 C24 C29 149.2(3) . . . . ?
N37 C38 C39 O40 57.2(3) . . . . ?
N37 C42 C41 O40 -57.2(3) . . . . ?
N7 S6 O5 C4 -56.4(2) . . . . ?
O43 S27 O28 C29 -170.0(2) . . . . ?
O43 S27 N26 C25 149.0(2) . . . . ?
N26 S27 O28 C29 -55.9(2) . . . . ?
N26 C25 C24 C23 149.0(3) . . . . ?
N26 C25 C24 C29 -28.6(4) . . . . ?
C9 C4 C3 C2 -2.5(5) . . . . ?
C9 C10 C14 C13 178.0(2) . . . . ?
C4 C9 C8 N15 153.6(2) . . . . ?
C4 C9 C8 N7 -26.4(4) . . . . ?
C4 C9 C10 C1 -8.5(3) . . . . ?
C4 C9 C10 C14 168.1(2) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C1 C10 C14 C13 -5.3(4) . . . . ?
C1 C11 C12 C13 -1.8(4) . . . . ?
C8 N15 C16 C17 153.0(2) . . . . ?
C8 N15 C20 C19 -149.2(3) . . . . ?
C8 C9 C4 O5 5.0(4) . . . . ?
C8 C9 C4 C3 -176.4(3) . . . . ?
C8 C9 C10 C1 176.1(2) . . . . ?
C8 C9 C10 C14 -7.3(4) . . . . ?
C31 C32 C23 C24 1.5(4) . . . . ?
C31 C32 C23 C33 -175.3(2) . . . . ?
C31 C32 C36 C35 177.3(3) . . . . ?
C32 C31 C30 C29 -2.4(4) . . . . ?
C32 C23 C24 C25 174.0(2) . . . . ?
C32 C23 C24 C29 -8.5(4) . . . . ?
C32 C23 C33 C34 -3.7(4) . . . . ?
C32 C36 C35 C34 -0.5(5) . . . . ?
C25 N37 C38 C39 154.5(3) . . . . ?
C25 N37 C42 C41 -153.2(3) . . . . ?
C25 C24 C29 O28 8.5(4) . . . . ?
C25 C24 C29 C30 -171.6(3) . . . . ?
C2 C1 C10 C9 4.6(4) . . . . ?
C2 C1 C10 C14 -172.3(2) . . . . ?
C2 C1 C11 C12 175.7(3) . . . . ?
C23 C32 C36 C35 -1.5(4) . . . . ?
C23 C24 C29 O28 -169.3(2) . . . . ?
C23 C24 C29 C30 10.7(4) . . . . ?
C23 C33 C34 C35 1.7(4) . . . . ?
C24 C23 C33 C34 179.7(3) . . . . ?
C24 C29 C30 C31 -5.2(4) . . . . ?
C10 C9 C4 O5 -170.8(2) . . . . ?
C10 C9 C4 C3 7.8(4) . . . . ?
C10 C9 C8 N15 -31.0(4) . . . . ?
C10 C9 C8 N7 149.0(3) . . . . ?
C10 C1 C2 C3 0.8(4) . . . . ?
C10 C1 C11 C12 -1.9(4) . . . . ?
C16 N15 C8 N7 141.1(2) . . . . ?
C16 N15 C8 C9 -38.8(4) . . . . ?
C16 N15 C20 C19 55.7(3) . . . . ?
C14 C13 C12 C11 1.9(4) . . . . ?
C11 C1 C2 C3 -176.8(3) . . . . ?
C11 C1 C10 C9 -177.8(2) . . . . ?
C11 C1 C10 C14 5.3(4) . . . . ?
C38 N37 C25 N26 143.7(3) . . . . ?
C38 N37 C25 C24 -34.1(4) . . . . ?
C38 N37 C42 C41 53.8(3) . . . . ?
C20 N15 C8 N7 -11.1(4) . . . . ?
C20 N15 C8 C9 169.0(2) . . . . ?
C20 N15 C16 C17 -53.0(3) . . . . ?
C33 C23 C24 C25 -9.4(4) . . . . ?
C33 C23 C24 C29 168.1(3) . . . . ?
C33 C34 C35 C36 0.4(5) . . . . ?
C36 C32 C23 C24 -179.7(2) . . . . ?
C36 C32 C23 C33 3.5(4) . . . . ?
C42 N37 C25 N26 -5.9(4) . . . . ?
C42 N37 C25 C24 176.2(2) . . . . ?
C42 N37 C38 C39 -53.7(3) . . . . ?
C19 O18 C17 C16 -58.7(3) . . . . ?
C30 C31 C32 C23 4.1(4) . . . . ?
C30 C31 C32 C36 -174.7(3) . . . . ?
C41 O40 C39 C38 -60.5(3) . . . . ?
C39 O40 C41 C42 60.6(3) . . . . ?
C12 C13 C14 C10 1.8(4) . . . . ?
C17 O18 C19 C20 62.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.714
