# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2047050'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2020-11-29 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H16 N2 O2 S'
_chemical_formula_sum            'C11 H16 N2 O2 S'
_chemical_formula_weight         240.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   13.48850(10)
_cell_length_b                   11.17670(10)
_cell_length_c                   16.4909(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.5440(10)
_cell_angle_gamma                90
_cell_volume                     2458.53(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6177
_cell_measurement_theta_min      2.7073
_cell_measurement_theta_max      76.3934

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    2.253
_shelx_estimated_absorpt_T_min   0.551
_shelx_estimated_absorpt_T_max   0.551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9855
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.957
_diffrn_reflns_theta_max         74.993
_diffrn_reflns_theta_full        74.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4995
_reflns_number_gt                4702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'

_refine_special_details          
;
The (1 3 0) relection was omitted owing to poor agreement
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+0.8508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4995
_refine_ls_number_parameters     307
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.65997(2) 0.21787(3) 0.03587(2) 0.01988(8) Uani 1 1 d . . . . .
O1 O 0.48400(7) 0.34005(9) 0.26220(6) 0.0245(2) Uani 1 1 d D . . . .
H1O H 0.4757(14) 0.3484(17) 0.3113(6) 0.037 Uiso 1 1 d D U . . .
O2 O 0.47200(7) 0.15776(9) -0.08984(5) 0.02193(19) Uani 1 1 d D . . . .
H2O H 0.5272(9) 0.1705(17) -0.0601(10) 0.033 Uiso 1 1 d D U . . .
N1 N 0.61060(8) 0.37232(10) 0.14769(7) 0.0200(2) Uani 1 1 d D . . . .
H1N H 0.5776(11) 0.3773(15) 0.1893(8) 0.024 Uiso 1 1 d D U . . .
N2 N 0.48341(7) 0.25217(9) 0.08894(6) 0.0146(2) Uani 1 1 d . . . . .
C1 C 0.58049(9) 0.28446(11) 0.09323(7) 0.0158(2) Uani 1 1 d . . . . .
C2 C 0.70032(9) 0.44020(11) 0.15420(8) 0.0194(2) Uani 1 1 d . . . . .
C3 C 0.72918(10) 0.49792(13) 0.08688(9) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.691723 0.487451 0.033849 0.033 Uiso 1 1 calc R U . . .
C4 C 0.81356(11) 0.57133(14) 0.09786(11) 0.0358(4) Uani 1 1 d . . . . .
H4 H 0.834014 0.610433 0.051952 0.043 Uiso 1 1 calc R U . . .
C5 C 0.86802(10) 0.58781(14) 0.17535(12) 0.0369(4) Uani 1 1 d . . . . .
H5 H 0.925032 0.638751 0.182444 0.044 Uiso 1 1 calc R U . . .
C6 C 0.83911(10) 0.52995(14) 0.24218(10) 0.0326(3) Uani 1 1 d . . . . .
H6 H 0.876591 0.540605 0.295188 0.039 Uiso 1 1 calc R U . . .
C7 C 0.75509(9) 0.45608(12) 0.23176(9) 0.0238(3) Uani 1 1 d . . . . .
H7 H 0.735156 0.416489 0.277693 0.029 Uiso 1 1 calc R U . . .
C8 C 0.40869(9) 0.32644(11) 0.12264(7) 0.0166(2) Uani 1 1 d . . . . .
H8A H 0.342862 0.316561 0.087732 0.020 Uiso 1 1 calc R U . . .
H8B H 0.428269 0.411552 0.119958 0.020 Uiso 1 1 calc R U . . .
C9 C 0.39741(9) 0.29630(11) 0.21032(7) 0.0180(2) Uani 1 1 d . . . . .
H9A H 0.336194 0.334281 0.225016 0.022 Uiso 1 1 calc R U . . .
H9B H 0.391673 0.208631 0.216822 0.022 Uiso 1 1 calc R U . . .
C10 C 0.44410(9) 0.13821(11) 0.05324(7) 0.0156(2) Uani 1 1 d . . . . .
H10A H 0.392695 0.108055 0.085173 0.019 Uiso 1 1 calc R U . . .
H10B H 0.499317 0.079067 0.058500 0.019 Uiso 1 1 calc R U . . .
C11 C 0.39806(9) 0.14691(12) -0.03631(7) 0.0187(2) Uani 1 1 d . . . . .
H11A H 0.357037 0.074654 -0.051538 0.022 Uiso 1 1 calc R U . . .
H11B H 0.352993 0.217226 -0.043794 0.022 Uiso 1 1 calc R U . . .
S21 S 0.66284(2) 0.32832(3) 0.55027(2) 0.01836(8) Uani 1 1 d . . . . .
O21 O 0.47525(7) 0.32689(10) 0.79517(6) 0.0287(2) Uani 1 1 d D . . . .
H21O H 0.4737(15) 0.2763(15) 0.8328(9) 0.043 Uiso 1 1 d D U . . .
O22 O 0.47149(7) 0.37786(9) 0.42055(5) 0.0239(2) Uani 1 1 d D . . . .
H22O H 0.5276(9) 0.3684(17) 0.4493(10) 0.036 Uiso 1 1 d D U . . .
N21 N 0.61909(7) 0.38751(9) 0.69936(6) 0.0153(2) Uani 1 1 d D . . . .
H21N H 0.5798(10) 0.3687(14) 0.7349(8) 0.018 Uiso 1 1 d D U . . .
N22 N 0.48697(7) 0.32651(9) 0.60673(6) 0.0145(2) Uani 1 1 d . . . . .
C21 C 0.58652(8) 0.34987(10) 0.62214(7) 0.0143(2) Uani 1 1 d . . . . .
C22 C 0.71198(8) 0.43751(10) 0.73357(7) 0.0144(2) Uani 1 1 d . . . . .
C23 C 0.77088(9) 0.50860(11) 0.69018(7) 0.0164(2) Uani 1 1 d . . . . .
H23 H 0.751386 0.522001 0.633157 0.020 Uiso 1 1 calc R U . . .
C24 C 0.85855(9) 0.55991(11) 0.73096(8) 0.0206(3) Uani 1 1 d . . . . .
H24 H 0.899386 0.606941 0.701113 0.025 Uiso 1 1 calc R U . . .
C25 C 0.88694(9) 0.54321(12) 0.81451(8) 0.0237(3) Uani 1 1 d . . . . .
H25 H 0.946670 0.578820 0.841820 0.028 Uiso 1 1 calc R U . . .
C26 C 0.82746(10) 0.47412(12) 0.85782(8) 0.0230(3) Uani 1 1 d . . . . .
H26 H 0.846145 0.463095 0.915174 0.028 Uiso 1 1 calc R U . . .
C27 C 0.74053(9) 0.42084(11) 0.81779(7) 0.0181(2) Uani 1 1 d . . . . .
H27 H 0.700456 0.372978 0.847795 0.022 Uiso 1 1 calc R U . . .
C28 C 0.41469(8) 0.37774(11) 0.65611(7) 0.0160(2) Uani 1 1 d . . . . .
H28A H 0.349848 0.389621 0.620155 0.019 Uiso 1 1 calc R U . . .
H28B H 0.439222 0.457407 0.676254 0.019 Uiso 1 1 calc R U . . .
C29 C 0.39687(9) 0.30241(12) 0.72882(8) 0.0210(3) Uani 1 1 d . . . . .
H29A H 0.330979 0.322249 0.744945 0.025 Uiso 1 1 calc R U . . .
H29B H 0.396973 0.216446 0.714347 0.025 Uiso 1 1 calc R U . . .
C30 C 0.44194(9) 0.25285(11) 0.53724(7) 0.0165(2) Uani 1 1 d . . . . .
H30A H 0.388580 0.202547 0.554821 0.020 Uiso 1 1 calc R U . . .
H30B H 0.493799 0.198762 0.521177 0.020 Uiso 1 1 calc R U . . .
C31 C 0.39746(9) 0.32617(12) 0.46315(7) 0.0189(2) Uani 1 1 d . . . . .
H31A H 0.353149 0.274201 0.424925 0.023 Uiso 1 1 calc R U . . .
H31B H 0.355735 0.390876 0.481353 0.023 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 C1 1.7028(12) . ?
O1 C9 1.4277(15) . ?
O1 H1O 0.838(9) . ?
O2 C11 1.4319(15) . ?
O2 H2O 0.841(9) . ?
N1 C1 1.3518(16) . ?
N1 C2 1.4188(15) . ?
N1 H1N 0.873(9) . ?
N2 C1 1.3499(15) . ?
N2 C10 1.4688(15) . ?
N2 C8 1.4766(14) . ?
C2 C3 1.3887(19) . ?
C2 C7 1.3902(18) . ?
C3 C4 1.3929(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3920(19) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.5141(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5178(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
S21 C21 1.6985(12) . ?
O21 C29 1.4304(16) . ?
O21 H21O 0.842(9) . ?
O22 C31 1.4259(15) . ?
O22 H22O 0.838(9) . ?
N21 C21 1.3511(15) . ?
N21 C22 1.4108(14) . ?
N21 H21N 0.873(9) . ?
N22 C21 1.3544(15) . ?
N22 C30 1.4673(15) . ?
N22 C28 1.4756(15) . ?
C22 C23 1.3941(17) . ?
C22 C27 1.3975(16) . ?
C23 C24 1.3939(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3868(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.3911(17) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.5134(17) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.5187(16) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?

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
C9 O1 H1O 113.7(13) . . ?
C11 O2 H2O 107.0(13) . . ?
C1 N1 C2 127.40(11) . . ?
C1 N1 H1N 115.5(11) . . ?
C2 N1 H1N 115.8(11) . . ?
C1 N2 C10 122.86(10) . . ?
C1 N2 C8 122.75(10) . . ?
C10 N2 C8 114.35(9) . . ?
N2 C1 N1 114.99(10) . . ?
N2 C1 S1 122.68(9) . . ?
N1 C1 S1 122.32(9) . . ?
C3 C2 C7 120.16(12) . . ?
C3 C2 N1 121.68(12) . . ?
C7 C2 N1 117.95(12) . . ?
C2 C3 C4 119.37(14) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.55(15) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.88(13) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 119.98(14) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 120.07(14) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N2 C8 C9 113.92(10) . . ?
N2 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N2 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O1 C9 C8 107.86(10) . . ?
O1 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
O1 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
N2 C10 C11 113.93(10) . . ?
N2 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O2 C11 C10 112.55(10) . . ?
O2 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O2 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C29 O21 H21O 109.8(14) . . ?
C31 O22 H22O 108.0(13) . . ?
C21 N21 C22 130.19(10) . . ?
C21 N21 H21N 114.4(10) . . ?
C22 N21 H21N 114.8(10) . . ?
C21 N22 C30 122.59(10) . . ?
C21 N22 C28 122.65(10) . . ?
C30 N22 C28 114.70(9) . . ?
N21 C21 N22 114.29(10) . . ?
N21 C21 S21 123.78(9) . . ?
N22 C21 S21 121.91(9) . . ?
C23 C22 C27 119.48(11) . . ?
C23 C22 N21 124.09(11) . . ?
C27 C22 N21 116.22(11) . . ?
C24 C23 C22 119.62(11) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C25 C24 C23 120.87(12) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 119.44(11) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 120.38(12) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 120.19(12) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
N22 C28 C29 114.65(10) . . ?
N22 C28 H28A 108.6 . . ?
C29 C28 H28A 108.6 . . ?
N22 C28 H28B 108.6 . . ?
C29 C28 H28B 108.6 . . ?
H28A C28 H28B 107.6 . . ?
O21 C29 C28 108.26(10) . . ?
O21 C29 H29A 110.0 . . ?
C28 C29 H29A 110.0 . . ?
O21 C29 H29B 110.0 . . ?
C28 C29 H29B 110.0 . . ?
H29A C29 H29B 108.4 . . ?
N22 C30 C31 113.19(10) . . ?
N22 C30 H30A 108.9 . . ?
C31 C30 H30A 108.9 . . ?
N22 C30 H30B 108.9 . . ?
C31 C30 H30B 108.9 . . ?
H30A C30 H30B 107.8 . . ?
O22 C31 C30 113.16(10) . . ?
O22 C31 H31A 108.9 . . ?
C30 C31 H31A 108.9 . . ?
O22 C31 H31B 108.9 . . ?
C30 C31 H31B 108.9 . . ?
H31A C31 H31B 107.8 . . ?

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
C10 N2 C1 N1 -161.48(11) . . . . ?
C8 N2 C1 N1 16.10(16) . . . . ?
C10 N2 C1 S1 17.34(16) . . . . ?
C8 N2 C1 S1 -165.08(9) . . . . ?
C2 N1 C1 N2 -166.51(12) . . . . ?
C2 N1 C1 S1 14.67(18) . . . . ?
C1 N1 C2 C3 51.55(19) . . . . ?
C1 N1 C2 C7 -133.78(14) . . . . ?
C7 C2 C3 C4 0.2(2) . . . . ?
N1 C2 C3 C4 174.79(13) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
N1 C2 C7 C6 -174.77(12) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C1 N2 C8 C9 -91.82(13) . . . . ?
C10 N2 C8 C9 85.95(12) . . . . ?
N2 C8 C9 O1 73.33(12) . . . . ?
C1 N2 C10 C11 -95.02(13) . . . . ?
C8 N2 C10 C11 87.21(12) . . . . ?
N2 C10 C11 O2 74.54(13) . . . . ?
C22 N21 C21 N22 -168.69(11) . . . . ?
C22 N21 C21 S21 13.32(18) . . . . ?
C30 N22 C21 N21 -161.47(10) . . . . ?
C28 N22 C21 N21 21.51(16) . . . . ?
C30 N22 C21 S21 16.56(16) . . . . ?
C28 N22 C21 S21 -160.46(9) . . . . ?
C21 N21 C22 C23 31.80(19) . . . . ?
C21 N21 C22 C27 -153.45(12) . . . . ?
C27 C22 C23 C24 1.41(17) . . . . ?
N21 C22 C23 C24 176.00(11) . . . . ?
C22 C23 C24 C25 -1.34(18) . . . . ?
C23 C24 C25 C26 0.3(2) . . . . ?
C24 C25 C26 C27 0.7(2) . . . . ?
C25 C26 C27 C22 -0.60(19) . . . . ?
C23 C22 C27 C26 -0.46(18) . . . . ?
N21 C22 C27 C26 -175.47(11) . . . . ?
C21 N22 C28 C29 -90.24(13) . . . . ?
C30 N22 C28 C29 92.52(12) . . . . ?
N22 C28 C29 O21 82.80(13) . . . . ?
C21 N22 C30 C31 -97.19(13) . . . . ?
C28 N22 C30 C31 80.05(12) . . . . ?
N22 C30 C31 O22 73.76(13) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2047052'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2020-11-29 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 Cl N2 O2 S'
_chemical_formula_sum            'C11 H15 Cl N2 O2 S'
_chemical_formula_weight         274.76

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.1366(2)
_cell_length_b                   10.7767(3)
_cell_length_c                   16.6259(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.221(2)
_cell_angle_gamma                90
_cell_volume                     1258.39(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2308
_cell_measurement_theta_min      2.6983
_cell_measurement_theta_max      76.2652

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.184
_shelx_estimated_absorpt_T_min   0.573
_shelx_estimated_absorpt_T_max   0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89367
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4685
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.914
_diffrn_reflns_theta_max         74.933
_diffrn_reflns_theta_full        74.933
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2554
_reflns_number_gt                2243
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.2198P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2554
_refine_ls_number_parameters     163
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cl1 Cl 0.80245(6) 0.59295(4) 0.47362(3) 0.02599(12) Uani 1 1 d . . . . .
S1 S 0.13297(5) 0.64270(4) 0.13426(2) 0.01620(11) Uani 1 1 d . . . . .
O1 O -0.15441(17) 0.92972(12) 0.30553(8) 0.0240(3) Uani 1 1 d D . . . .
H1O H -0.180(3) 0.958(2) 0.3492(9) 0.036 Uiso 1 1 d D U . . .
O2 O -0.26300(17) 0.52693(11) 0.05416(8) 0.0195(3) Uani 1 1 d D . . . .
H2O H -0.1480(15) 0.544(2) 0.0634(13) 0.029 Uiso 1 1 d D U . . .
N1 N 0.05327(19) 0.72513(14) 0.27682(8) 0.0172(3) Uani 1 1 d D . . . .
H1N H -0.004(3) 0.7849(14) 0.2993(11) 0.021 Uiso 1 1 d D U . . .
N2 N -0.19119(18) 0.73888(12) 0.16804(8) 0.0132(3) Uani 1 1 d . . . . .
C1 C -0.0088(2) 0.70438(14) 0.19580(10) 0.0133(3) Uani 1 1 d . . . . .
C2 C 0.2332(2) 0.69068(15) 0.32209(9) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.2987(2) 0.56889(15) 0.32485(10) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.223863 0.506315 0.294262 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4728(2) 0.53854(16) 0.37206(11) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.518225 0.455553 0.373733 0.023 Uiso 1 1 calc R U . . .
C5 C 0.5801(2) 0.63075(16) 0.41686(10) 0.0165(3) Uani 1 1 d . . . . .
C6 C 0.5162(2) 0.75170(16) 0.41644(10) 0.0162(3) Uani 1 1 d . . . . .
H6 H 0.590218 0.813474 0.448237 0.019 Uiso 1 1 calc R U . . .
C7 C 0.3416(2) 0.78163(15) 0.36864(9) 0.0159(3) Uani 1 1 d . . . . .
H7 H 0.295876 0.864512 0.367721 0.019 Uiso 1 1 calc R U . . .
C8 C -0.3272(2) 0.76749(16) 0.22264(10) 0.0160(3) Uani 1 1 d . . . . .
H8A H -0.297522 0.714467 0.271885 0.019 Uiso 1 1 calc R U . . .
H8B H -0.457067 0.745975 0.194308 0.019 Uiso 1 1 calc R U . . .
C9 C -0.3255(2) 0.90244(16) 0.24936(10) 0.0184(3) Uani 1 1 d . . . . .
H9A H -0.334752 0.957028 0.200921 0.022 Uiso 1 1 calc R U . . .
H9B H -0.437057 0.918841 0.275684 0.022 Uiso 1 1 calc R U . . .
C10 C -0.2666(2) 0.75086(15) 0.08015(9) 0.0146(3) Uani 1 1 d . . . . .
H10A H -0.159341 0.765499 0.050865 0.018 Uiso 1 1 calc R U . . .
H10B H -0.351316 0.824189 0.071287 0.018 Uiso 1 1 calc R U . . .
C11 C -0.3766(2) 0.63750(15) 0.04398(10) 0.0171(3) Uani 1 1 d . . . . .
H11A H -0.488947 0.625879 0.070602 0.020 Uiso 1 1 calc R U . . .
H11B H -0.423125 0.651626 -0.015020 0.020 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
Cl1 C5 1.7448(17) . ?
S1 C1 1.6968(16) . ?
O1 C9 1.430(2) . ?
O1 H1O 0.836(9) . ?
O2 C11 1.434(2) . ?
O2 H2O 0.829(9) . ?
N1 C1 1.360(2) . ?
N1 C2 1.418(2) . ?
N1 H1N 0.880(9) . ?
N2 C1 1.354(2) . ?
N2 C10 1.4705(19) . ?
N2 C8 1.4743(19) . ?
C2 C3 1.391(2) . ?
C2 C7 1.395(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(2) . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.520(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.518(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C9 O1 H1O 110.6(17) . . ?
C11 O2 H2O 110.7(16) . . ?
C1 N1 C2 126.00(14) . . ?
C1 N1 H1N 116.6(13) . . ?
C2 N1 H1N 114.2(13) . . ?
C1 N2 C10 121.54(13) . . ?
C1 N2 C8 123.07(13) . . ?
C10 N2 C8 115.39(12) . . ?
N2 C1 N1 114.64(14) . . ?
N2 C1 S1 122.83(12) . . ?
N1 C1 S1 122.52(12) . . ?
C3 C2 C7 119.65(15) . . ?
C3 C2 N1 122.14(15) . . ?
C7 C2 N1 118.11(15) . . ?
C4 C3 C2 120.24(15) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.25(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.56(15) . . ?
C6 C5 Cl1 119.41(13) . . ?
C4 C5 Cl1 119.03(13) . . ?
C5 C6 C7 118.88(15) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 120.40(15) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N2 C8 C9 114.09(14) . . ?
N2 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
O1 C9 C8 110.42(13) . . ?
O1 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
O1 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C11 113.29(13) . . ?
N2 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
O2 C11 C10 112.34(13) . . ?
O2 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O2 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 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
C10 N2 C1 N1 165.29(14) . . . . ?
C8 N2 C1 N1 -14.4(2) . . . . ?
C10 N2 C1 S1 -13.6(2) . . . . ?
C8 N2 C1 S1 166.73(12) . . . . ?
C2 N1 C1 N2 175.81(15) . . . . ?
C2 N1 C1 S1 -5.3(2) . . . . ?
C1 N1 C2 C3 -55.6(2) . . . . ?
C1 N1 C2 C7 128.01(17) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
N1 C2 C3 C4 -177.84(15) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C3 C4 C5 Cl1 -178.00(13) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
Cl1 C5 C6 C7 177.75(12) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C3 C2 C7 C6 1.3(2) . . . . ?
N1 C2 C7 C6 177.74(14) . . . . ?
C1 N2 C8 C9 88.74(18) . . . . ?
C10 N2 C8 C9 -90.96(16) . . . . ?
N2 C8 C9 O1 -71.15(17) . . . . ?
C1 N2 C10 C11 97.77(17) . . . . ?
C8 N2 C10 C11 -82.53(17) . . . . ?
N2 C10 C11 O2 -58.80(18) . . . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2047053'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2020-11-29 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N3 O4 S'
_chemical_formula_sum            'C11 H15 N3 O4 S'
_chemical_formula_weight         285.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8235(5)
_cell_length_b                   11.2124(5)
_cell_length_c                   12.3443(5)
_cell_angle_alpha                90.050(3)
_cell_angle_beta                 108.737(4)
_cell_angle_gamma                114.559(4)
_cell_volume                     1274.53(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8498
_cell_measurement_theta_min      2.2430
_cell_measurement_theta_max      27.5022

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5859
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5859
_reflns_number_gt                4753
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'

_refine_special_details          
;
 Refined as a 2-component twin. The minor component was present 
 of the time.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+0.6151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5859
_refine_ls_number_parameters     362
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.49065(5) 0.62736(5) 0.60685(4) 0.01865(12) Uani 1 1 d . . . . .
O1 O 0.16698(15) 0.81104(14) 0.62422(12) 0.0198(3) Uani 1 1 d D . . . .
H1O H 0.2543(13) 0.8634(19) 0.638(2) 0.030 Uiso 1 1 d D U . . .
O2 O 0.44094(16) 0.46874(14) 0.81315(13) 0.0230(3) Uani 1 1 d D . . . .
H2O H 0.481(3) 0.506(2) 0.7666(19) 0.034 Uiso 1 1 d D U . . .
O3 O 0.18815(17) 0.49237(16) 0.00661(13) 0.0301(4) Uani 1 1 d . . . . .
O4 O 0.13103(16) 0.65669(16) -0.01040(12) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.22939(17) 0.62933(16) 0.51687(13) 0.0150(3) Uani 1 1 d D . . . .
H1N H 0.184(2) 0.6740(19) 0.5299(19) 0.018 Uiso 1 1 d D U . . .
N2 N 0.31921(16) 0.64714(15) 0.71365(13) 0.0127(3) Uani 1 1 d . . . . .
N3 N 0.16505(17) 0.57851(17) 0.04687(14) 0.0217(4) Uani 1 1 d . . . . .
C1 C 0.34001(19) 0.63391(17) 0.61350(15) 0.0135(4) Uani 1 1 d . . . . .
C2 C 0.21563(18) 0.61148(18) 0.40008(15) 0.0134(4) Uani 1 1 d . . . . .
C3 C 0.24885(19) 0.51984(18) 0.35346(16) 0.0154(4) Uani 1 1 d . . . . .
H3 H 0.283176 0.465605 0.401175 0.018 Uiso 1 1 calc R U . . .
C4 C 0.2313(2) 0.50882(19) 0.23721(16) 0.0171(4) Uani 1 1 d . . . . .
H4 H 0.254979 0.447960 0.204776 0.020 Uiso 1 1 calc R U . . .
C5 C 0.17903(19) 0.58707(18) 0.16862(15) 0.0158(4) Uani 1 1 d . . . . .
C6 C 0.14012(19) 0.67472(19) 0.21221(16) 0.0167(4) Uani 1 1 d . . . . .
H6 H 0.101740 0.725757 0.163234 0.020 Uiso 1 1 calc R U . . .
C7 C 0.15830(19) 0.68630(19) 0.32833(16) 0.0158(4) Uani 1 1 d . . . . .
H7 H 0.131681 0.745475 0.359628 0.019 Uiso 1 1 calc R U . . .
C8 C 0.17783(19) 0.62465(18) 0.72071(16) 0.0151(4) Uani 1 1 d . . . . .
H8A H 0.168010 0.583973 0.790475 0.018 Uiso 1 1 calc R U . . .
H8B H 0.098972 0.561347 0.652136 0.018 Uiso 1 1 calc R U . . .
C9 C 0.1607(2) 0.7521(2) 0.72627(17) 0.0197(4) Uani 1 1 d . . . . .
H9A H 0.066418 0.732580 0.734497 0.024 Uiso 1 1 calc R U . . .
H9B H 0.238859 0.815542 0.795089 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4393(2) 0.68652(19) 0.82511(15) 0.0164(4) Uani 1 1 d . . . . .
H10A H 0.430455 0.748159 0.876323 0.020 Uiso 1 1 calc R U . . .
H10B H 0.532226 0.734910 0.812200 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4434(2) 0.5701(2) 0.88540(17) 0.0207(4) Uani 1 1 d . . . . .
H11A H 0.532481 0.602329 0.955283 0.025 Uiso 1 1 calc R U . . .
H11B H 0.358883 0.531461 0.910980 0.025 Uiso 1 1 calc R U . . .
S21 S 0.49397(5) 0.13042(5) 0.88624(4) 0.01729(12) Uani 1 1 d . . . . .
O21 O 0.15692(15) 0.30733(14) 0.68580(13) 0.0219(3) Uani 1 1 d D . . . .
H21O H 0.2417(14) 0.3622(19) 0.724(2) 0.033 Uiso 1 1 d D U . . .
O22 O 0.44733(16) -0.02540(14) 0.65048(12) 0.0223(3) Uani 1 1 d D . . . .
H22O H 0.488(3) 0.014(2) 0.7191(11) 0.033 Uiso 1 1 d D U . . .
O23 O 0.14670(17) -0.02670(15) 1.30089(13) 0.0281(3) Uani 1 1 d . . . . .
O24 O 0.11110(17) 0.14931(16) 1.29461(13) 0.0278(3) Uani 1 1 d . . . . .
N21 N 0.23420(17) 0.13540(16) 0.83230(13) 0.0154(3) Uani 1 1 d D . . . .
H21N H 0.185(2) 0.176(2) 0.7919(17) 0.018 Uiso 1 1 d D U . . .
N22 N 0.31869(16) 0.14788(15) 0.68384(13) 0.0128(3) Uani 1 1 d . . . . .
N23 N 0.14087(17) 0.06864(17) 1.25474(14) 0.0190(3) Uani 1 1 d . . . . .
C21 C 0.34269(19) 0.13727(17) 0.79648(15) 0.0128(3) Uani 1 1 d . . . . .
C22 C 0.21918(18) 0.11700(18) 0.94048(15) 0.0132(3) Uani 1 1 d . . . . .
C23 C 0.25300(19) 0.02655(18) 1.00722(16) 0.0148(4) Uani 1 1 d . . . . .
H23 H 0.292699 -0.024443 0.981623 0.018 Uiso 1 1 calc R U . . .
C24 C 0.22827(19) 0.01180(18) 1.11079(16) 0.0151(4) Uani 1 1 d . . . . .
H24 H 0.251755 -0.048671 1.157160 0.018 Uiso 1 1 calc R U . . .
C25 C 0.16879(19) 0.08624(18) 1.14628(15) 0.0143(4) Uani 1 1 d . . . . .
C26 C 0.13292(19) 0.17505(18) 1.08083(16) 0.0158(4) Uani 1 1 d . . . . .
H26 H 0.091636 0.224591 1.106239 0.019 Uiso 1 1 calc R U . . .
C27 C 0.15837(19) 0.19016(18) 0.97784(16) 0.0153(4) Uani 1 1 d . . . . .
H27 H 0.134418 0.250728 0.931911 0.018 Uiso 1 1 calc R U . . .
C28 C 0.17514(19) 0.12262(19) 0.59874(16) 0.0160(4) Uani 1 1 d . . . . .
H28A H 0.098449 0.059715 0.625128 0.019 Uiso 1 1 calc R U . . .
H28B H 0.163632 0.080188 0.523501 0.019 Uiso 1 1 calc R U . . .
C29 C 0.1543(2) 0.2480(2) 0.58145(17) 0.0216(4) Uani 1 1 d . . . . .
H29A H 0.232409 0.312359 0.557218 0.026 Uiso 1 1 calc R U . . .
H29B H 0.060250 0.226246 0.518946 0.026 Uiso 1 1 calc R U . . .
C30 C 0.4362(2) 0.18829(18) 0.63739(16) 0.0156(4) Uani 1 1 d . . . . .
H30A H 0.530168 0.237362 0.701500 0.019 Uiso 1 1 calc R U . . .
H30B H 0.424864 0.249569 0.581483 0.019 Uiso 1 1 calc R U . . .
C31 C 0.4399(2) 0.07230(19) 0.57754(17) 0.0196(4) Uani 1 1 d . . . . .
H31A H 0.351602 0.030268 0.507253 0.024 Uiso 1 1 calc R U . . .
H31B H 0.525169 0.105716 0.552789 0.024 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 C1 1.6900(18) . ?
O1 C9 1.431(2) . ?
O1 H1O 0.838(10) . ?
O2 C11 1.431(2) . ?
O2 H2O 0.837(10) . ?
O3 N3 1.234(2) . ?
O4 N3 1.227(2) . ?
N1 C1 1.375(2) . ?
N1 C2 1.406(2) . ?
N1 H1N 0.878(9) . ?
N2 C1 1.344(2) . ?
N2 C10 1.467(2) . ?
N2 C8 1.476(2) . ?
N3 C5 1.460(2) . ?
C2 C7 1.398(3) . ?
C2 C3 1.398(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.520(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.512(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
S21 C21 1.6893(18) . ?
O21 C29 1.436(2) . ?
O21 H21O 0.834(10) . ?
O22 C31 1.430(2) . ?
O22 H22O 0.838(10) . ?
O23 N23 1.227(2) . ?
O24 N23 1.228(2) . ?
N21 C21 1.374(2) . ?
N21 C22 1.402(2) . ?
N21 H21N 0.878(9) . ?
N22 C21 1.345(2) . ?
N22 C30 1.464(2) . ?
N22 C28 1.477(2) . ?
N23 C25 1.461(2) . ?
C22 C23 1.399(3) . ?
C22 C27 1.401(2) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(3) . ?
C26 C27 1.381(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.518(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.516(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?

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
C9 O1 H1O 106.5(17) . . ?
C11 O2 H2O 107.3(18) . . ?
C1 N1 C2 128.13(15) . . ?
C1 N1 H1N 113.5(14) . . ?
C2 N1 H1N 113.3(14) . . ?
C1 N2 C10 121.06(15) . . ?
C1 N2 C8 123.67(15) . . ?
C10 N2 C8 115.27(14) . . ?
O4 N3 O3 123.18(17) . . ?
O4 N3 C5 118.81(16) . . ?
O3 N3 C5 118.01(17) . . ?
N2 C1 N1 114.09(15) . . ?
N2 C1 S1 123.09(14) . . ?
N1 C1 S1 122.81(14) . . ?
C7 C2 C3 120.04(16) . . ?
C7 C2 N1 116.36(15) . . ?
C3 C2 N1 123.51(16) . . ?
C4 C3 C2 119.43(17) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 119.51(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.90(17) . . ?
C4 C5 N3 119.47(16) . . ?
C6 C5 N3 118.64(17) . . ?
C7 C6 C5 118.62(17) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C2 120.40(16) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N2 C8 C9 112.49(15) . . ?
N2 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O1 C9 C8 111.03(15) . . ?
O1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C11 113.17(15) . . ?
N2 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
O2 C11 C10 112.94(15) . . ?
O2 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
O2 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C29 O21 H21O 109.4(18) . . ?
C31 O22 H22O 107.3(18) . . ?
C21 N21 C22 128.95(15) . . ?
C21 N21 H21N 114.4(15) . . ?
C22 N21 H21N 113.4(14) . . ?
C21 N22 C30 121.47(15) . . ?
C21 N22 C28 123.44(15) . . ?
C30 N22 C28 115.08(14) . . ?
O23 N23 O24 123.19(17) . . ?
O23 N23 C25 118.50(15) . . ?
O24 N23 C25 118.30(16) . . ?
N22 C21 N21 113.74(15) . . ?
N22 C21 S21 123.10(13) . . ?
N21 C21 S21 123.14(14) . . ?
C23 C22 C27 119.85(16) . . ?
C23 C22 N21 124.12(16) . . ?
C27 C22 N21 115.92(16) . . ?
C24 C23 C22 119.61(16) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 119.40(17) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 121.89(17) . . ?
C26 C25 N23 119.00(16) . . ?
C24 C25 N23 119.10(16) . . ?
C27 C26 C25 118.63(16) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C26 C27 C22 120.61(17) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
N22 C28 C29 112.99(15) . . ?
N22 C28 H28A 109.0 . . ?
C29 C28 H28A 109.0 . . ?
N22 C28 H28B 109.0 . . ?
C29 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
O21 C29 C28 111.34(15) . . ?
O21 C29 H29A 109.4 . . ?
C28 C29 H29A 109.4 . . ?
O21 C29 H29B 109.4 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
N22 C30 C31 113.18(15) . . ?
N22 C30 H30A 108.9 . . ?
C31 C30 H30A 108.9 . . ?
N22 C30 H30B 108.9 . . ?
C31 C30 H30B 108.9 . . ?
H30A C30 H30B 107.8 . . ?
O22 C31 C30 112.57(15) . . ?
O22 C31 H31A 109.1 . . ?
C30 C31 H31A 109.1 . . ?
O22 C31 H31B 109.1 . . ?
C30 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?

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
C10 N2 C1 N1 -164.65(15) . . . . ?
C8 N2 C1 N1 15.0(2) . . . . ?
C10 N2 C1 S1 13.9(2) . . . . ?
C8 N2 C1 S1 -166.45(13) . . . . ?
C2 N1 C1 N2 -177.54(17) . . . . ?
C2 N1 C1 S1 3.9(3) . . . . ?
C1 N1 C2 C7 -141.22(19) . . . . ?
C1 N1 C2 C3 42.1(3) . . . . ?
C7 C2 C3 C4 3.2(3) . . . . ?
N1 C2 C3 C4 179.72(17) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C3 C4 C5 N3 178.00(16) . . . . ?
O4 N3 C5 C4 -173.55(17) . . . . ?
O3 N3 C5 C4 6.5(3) . . . . ?
O4 N3 C5 C6 6.0(3) . . . . ?
O3 N3 C5 C6 -173.95(17) . . . . ?
C4 C5 C6 C7 1.9(3) . . . . ?
N3 C5 C6 C7 -177.69(16) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C3 C2 C7 C6 -2.9(3) . . . . ?
N1 C2 C7 C6 -179.66(16) . . . . ?
C1 N2 C8 C9 -94.7(2) . . . . ?
C10 N2 C8 C9 85.03(19) . . . . ?
N2 C8 C9 O1 61.7(2) . . . . ?
C1 N2 C10 C11 -97.8(2) . . . . ?
C8 N2 C10 C11 82.52(19) . . . . ?
N2 C10 C11 O2 52.5(2) . . . . ?
C30 N22 C21 N21 162.69(16) . . . . ?
C28 N22 C21 N21 -16.2(2) . . . . ?
C30 N22 C21 S21 -16.0(2) . . . . ?
C28 N22 C21 S21 165.12(13) . . . . ?
C22 N21 C21 N22 175.49(17) . . . . ?
C22 N21 C21 S21 -5.8(3) . . . . ?
C21 N21 C22 C23 -39.5(3) . . . . ?
C21 N21 C22 C27 144.25(19) . . . . ?
C27 C22 C23 C24 -1.1(3) . . . . ?
N21 C22 C23 C24 -177.19(17) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C23 C24 C25 N23 179.04(16) . . . . ?
O23 N23 C25 C26 166.39(17) . . . . ?
O24 N23 C25 C26 -12.8(3) . . . . ?
O23 N23 C25 C24 -12.5(3) . . . . ?
O24 N23 C25 C24 168.26(17) . . . . ?
C24 C25 C26 C27 -0.5(3) . . . . ?
N23 C25 C26 C27 -179.38(16) . . . . ?
C25 C26 C27 C22 0.0(3) . . . . ?
C23 C22 C27 C26 0.8(3) . . . . ?
N21 C22 C27 C26 177.17(17) . . . . ?
C21 N22 C28 C29 94.7(2) . . . . ?
C30 N22 C28 C29 -84.23(19) . . . . ?
N22 C28 C29 O21 -63.9(2) . . . . ?
C21 N22 C30 C31 99.19(19) . . . . ?
C28 N22 C30 C31 -81.83(19) . . . . ?
N22 C30 C31 O22 -55.1(2) . . . . ?

_refine_diff_density_max         0.816
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2047051'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2020-11-29 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 N2 O2 S'
_chemical_formula_sum            'C12 H18 N2 O2 S'
_chemical_formula_weight         254.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.0472(2)
_cell_length_b                   10.7489(2)
_cell_length_c                   16.9533(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.109(2)
_cell_angle_gamma                90
_cell_volume                     1268.01(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2864
_cell_measurement_theta_min      2.6375
_cell_measurement_theta_max      74.9849

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.213
_shelx_estimated_absorpt_T_min   0.733
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7325
_exptl_absorpt_correction_T_max  0.8974
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5049
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.889
_diffrn_reflns_theta_max         74.967
_diffrn_reflns_theta_full        74.967
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2586
_reflns_number_gt                2346
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'

_refine_special_details          
;
The (-1 0 7) reflection was omitted owing to poor agreement
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+0.4557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     164
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.13641(4) 0.36081(3) 0.63490(2) 0.01627(10) Uani 1 1 d . . . . .
O1 O -0.16365(14) 0.08002(10) 0.80634(6) 0.0261(2) Uani 1 1 d D . . . .
H1O H -0.193(3) 0.0554(18) 0.8497(8) 0.039 Uiso 1 1 d D U . . .
O2 O -0.25720(14) 0.47884(9) 0.55586(6) 0.0204(2) Uani 1 1 d D . . . .
H2O H -0.1412(15) 0.4575(17) 0.5641(11) 0.031 Uiso 1 1 d D U . . .
N1 N 0.04973(16) 0.28284(11) 0.77557(6) 0.0175(2) Uani 1 1 d D . . . .
H1N H -0.014(2) 0.2254(12) 0.7969(9) 0.021 Uiso 1 1 d D U . . .
N2 N -0.19397(15) 0.26837(10) 0.67006(6) 0.0140(2) Uani 1 1 d . . . . .
C1 C -0.00958(18) 0.30184(11) 0.69636(7) 0.0144(2) Uani 1 1 d . . . . .
C2 C 0.23071(18) 0.31551(12) 0.82057(7) 0.0154(2) Uani 1 1 d . . . . .
C3 C 0.30569(19) 0.43511(12) 0.82163(8) 0.0182(3) Uani 1 1 d . . . . .
H3 H 0.239487 0.498223 0.788982 0.022 Uiso 1 1 calc R U . . .
C4 C 0.47829(19) 0.46199(12) 0.87077(8) 0.0190(3) Uani 1 1 d . . . . .
H4 H 0.529388 0.543782 0.870847 0.023 Uiso 1 1 calc R U . . .
C5 C 0.57807(18) 0.37166(13) 0.91993(7) 0.0170(3) Uani 1 1 d . . . . .
C5' C 0.7675(2) 0.40073(14) 0.97206(8) 0.0245(3) Uani 1 1 d . . . . .
H5A H 0.790857 0.340504 1.015924 0.037 Uiso 1 1 calc R U . . .
H5B H 0.763007 0.484846 0.993976 0.037 Uiso 1 1 calc R U . . .
H5C H 0.871533 0.395667 0.940048 0.037 Uiso 1 1 calc R U . . .
C6 C 0.50014(19) 0.25284(13) 0.91872(7) 0.0175(3) Uani 1 1 d . . . . .
H6 H 0.565473 0.189908 0.951811 0.021 Uiso 1 1 calc R U . . .
C7 C 0.32742(19) 0.22455(12) 0.86966(7) 0.0168(3) Uani 1 1 d . . . . .
H7 H 0.275722 0.142936 0.869789 0.020 Uiso 1 1 calc R U . . .
C8 C -0.33378(18) 0.24222(12) 0.72396(7) 0.0166(3) Uani 1 1 d . . . . .
H8A H -0.464011 0.263748 0.696240 0.020 Uiso 1 1 calc R U . . .
H8B H -0.305047 0.296544 0.771506 0.020 Uiso 1 1 calc R U . . .
C9 C -0.33410(19) 0.10747(13) 0.75148(8) 0.0197(3) Uani 1 1 d . . . . .
H9A H -0.448137 0.092371 0.777559 0.024 Uiso 1 1 calc R U . . .
H9B H -0.342367 0.051636 0.704621 0.024 Uiso 1 1 calc R U . . .
C10 C -0.26799(18) 0.25552(12) 0.58442(7) 0.0156(3) Uani 1 1 d . . . . .
H10A H -0.355204 0.182829 0.576580 0.019 Uiso 1 1 calc R U . . .
H10B H -0.158960 0.238743 0.555620 0.019 Uiso 1 1 calc R U . . .
C11 C -0.37542(19) 0.36935(12) 0.54803(8) 0.0182(3) Uani 1 1 d . . . . .
H11A H -0.422053 0.353634 0.490702 0.022 Uiso 1 1 calc R U . . .
H11B H -0.488874 0.383776 0.574600 0.022 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 C1 1.6986(13) . ?
O1 C9 1.4287(16) . ?
O1 H1O 0.838(9) . ?
O2 C11 1.4359(16) . ?
O2 H2O 0.840(9) . ?
N1 C1 1.3573(16) . ?
N1 C2 1.4226(16) . ?
N1 H1N 0.873(9) . ?
N2 C1 1.3539(16) . ?
N2 C10 1.4695(15) . ?
N2 C8 1.4730(16) . ?
C2 C3 1.3890(18) . ?
C2 C7 1.3905(18) . ?
C3 C4 1.3915(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3951(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3891(19) . ?
C5 C5' 1.5126(17) . ?
C5' H5A 0.9800 . ?
C5' H5B 0.9800 . ?
C5' H5C 0.9800 . ?
C6 C7 1.3947(18) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.5217(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5176(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C9 O1 H1O 109.8(14) . . ?
C11 O2 H2O 109.1(13) . . ?
C1 N1 C2 127.08(11) . . ?
C1 N1 H1N 114.7(11) . . ?
C2 N1 H1N 115.3(11) . . ?
C1 N2 C10 121.49(11) . . ?
C1 N2 C8 123.22(10) . . ?
C10 N2 C8 115.29(10) . . ?
N2 C1 N1 114.52(11) . . ?
N2 C1 S1 122.69(9) . . ?
N1 C1 S1 122.78(10) . . ?
C3 C2 C7 119.58(12) . . ?
C3 C2 N1 122.84(12) . . ?
C7 C2 N1 117.40(12) . . ?
C2 C3 C4 119.65(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 121.55(13) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 118.06(12) . . ?
C6 C5 C5' 120.59(12) . . ?
C4 C5 C5' 121.34(12) . . ?
C5 C5' H5A 109.5 . . ?
C5 C5' H5B 109.5 . . ?
H5A C5' H5B 109.5 . . ?
C5 C5' H5C 109.5 . . ?
H5A C5' H5C 109.5 . . ?
H5B C5' H5C 109.5 . . ?
C5 C6 C7 120.99(12) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 120.16(12) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N2 C8 C9 113.92(11) . . ?
N2 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N2 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O1 C9 C8 110.75(11) . . ?
O1 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C11 113.71(10) . . ?
N2 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O2 C11 C10 112.23(10) . . ?
O2 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
O2 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 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
C10 N2 C1 N1 -165.83(11) . . . . ?
C8 N2 C1 N1 14.07(17) . . . . ?
C10 N2 C1 S1 13.32(16) . . . . ?
C8 N2 C1 S1 -166.78(9) . . . . ?
C2 N1 C1 N2 -176.06(12) . . . . ?
C2 N1 C1 S1 4.79(19) . . . . ?
C1 N1 C2 C3 53.74(19) . . . . ?
C1 N1 C2 C7 -131.09(14) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
N1 C2 C3 C4 176.16(12) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C3 C4 C5 C5' 178.82(13) . . . . ?
C4 C5 C6 C7 0.15(19) . . . . ?
C5' C5 C6 C7 -178.72(12) . . . . ?
C3 C2 C7 C6 -0.99(19) . . . . ?
N1 C2 C7 C6 -176.33(11) . . . . ?
C5 C6 C7 C2 0.4(2) . . . . ?
C1 N2 C8 C9 -88.33(14) . . . . ?
C10 N2 C8 C9 91.58(13) . . . . ?
N2 C8 C9 O1 71.13(14) . . . . ?
C1 N2 C10 C11 -97.41(14) . . . . ?
C8 N2 C10 C11 82.69(13) . . . . ?
N2 C10 C11 O2 59.47(14) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045

