# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_zmc-20190408
_database_code_depnum_ccdc_archive 'CCDC 2102585'
_audit_update_record             
;
2021-08-11 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
_audit_creation_date             2021-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 N2 O2 S'
_chemical_formula_sum            'C13 H14 N2 O2 S'
_chemical_formula_weight         262.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1'
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'

_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                   13.7357(9)
_cell_length_b                   15.0653(8)
_cell_length_c                   6.8017(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.185(6)
_cell_angle_gamma                90
_cell_volume                     1406.47(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2958
_cell_measurement_temperature    294.78(10)
_cell_measurement_theta_max      23.3490
_cell_measurement_theta_min      4.0000
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12936
_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    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11515
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.666
_diffrn_reflns_theta_min         3.288
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.78(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  50.00   1.00   15.00    --   10.83-163.00  75.00   26
  2  ω      4.00  29.00   1.00   15.00    --   10.83-117.00-134.00   25
  3  ω    -63.00 -38.00   1.00   15.00    --  -11.77 117.00 -47.00   25
  4  ω    -91.00 -66.00   1.00   15.00    --  -11.77 163.00 102.00   25
  5  ω     41.00  95.00   1.00   15.00    --   10.83-178.00  30.00   54
  6  ω     -9.00  84.00   1.00   15.00    --   10.83  38.00-180.00   93
  7  ω    -12.00  28.00   1.00   15.00    --  -11.77 -99.00  60.00   40
  8  ω    -77.00 -42.00   1.00   15.00    --  -11.77 -57.00 150.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0432301000
_diffrn_orient_matrix_UB_12      0.0018410000
_diffrn_orient_matrix_UB_13      -0.0536119000
_diffrn_orient_matrix_UB_21      -0.0061347000
_diffrn_orient_matrix_UB_22      0.0464590000
_diffrn_orient_matrix_UB_23      -0.0120519000
_diffrn_orient_matrix_UB_31      0.0275694000
_diffrn_orient_matrix_UB_32      0.0074022000
_diffrn_orient_matrix_UB_33      0.0888127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1691
_reflns_number_total             3451
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1505
_refine_ls_R_factor_gt           0.0805
_refine_ls_restrained_S_all      1.026
_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)+(0.0602P)²+1.6451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1854
_refine_ls_wR_factor_ref         0.2240
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00d), C00E(H00h), C00F(H00i), C00G(H00j), C00H(H00k),
 C00I(H00l)
2.b Idealised Me refined as rotating group:
 C00A(H00a,H00b,H00c), C00D(H00e,H00f,H00g)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.52900(10) 0.42308(8) 0.76795(18) 0.0897(5) Uani 1 1 d . . . . .
O002 O 0.3435(2) 0.29947(17) 0.1924(4) 0.0827(9) Uani 1 1 d . . . . .
O003 O 0.2110(2) 0.3197(2) 0.5305(5) 0.0850(9) Uani 1 1 d . . . . .
H003 H 0.237031 0.277282 0.586811 0.128 Uiso 1 1 calc GR . . . .
N004 N 0.4459(2) 0.35490(18) 0.4352(4) 0.0631(8) Uani 1 1 d . . . . .
N005 N 0.3433(3) 0.4099(2) 0.6430(4) 0.0669(9) Uani 1 1 d . . . . .
C006 C 0.3581(3) 0.3388(2) 0.3485(6) 0.0644(10) Uani 1 1 d . . . . .
C007 C 0.4374(3) 0.3965(2) 0.6170(5) 0.0632(10) Uani 1 1 d . . . . .
C008 C 0.2815(3) 0.3794(2) 0.4761(6) 0.0667(10) Uani 1 1 d . . . . .
C009 C 0.2385(4) 0.4600(3) 0.3706(6) 0.0847(13) Uani 1 1 d . . . . .
H009 H 0.281870 0.504606 0.338533 0.102 Uiso 1 1 calc R . . . .
C00A C 0.5377(4) 0.3303(3) 0.3507(8) 0.0894(14) Uani 1 1 d . . . . .
H00A H 0.550966 0.268787 0.377368 0.134 Uiso 1 1 calc GR . . . .
H00B H 0.589180 0.366056 0.407872 0.134 Uiso 1 1 calc GR . . . .
H00C H 0.533464 0.339685 0.211049 0.134 Uiso 1 1 calc GR . . . .
C00B C 0.1125(4) 0.5541(4) 0.2209(6) 0.0905(15) Uani 1 1 d . . . . .
C00C C 0.1526(4) 0.4723(4) 0.3232(7) 0.0928(14) Uani 1 1 d . . . . .
H00D H 0.108625 0.427749 0.352741 0.111 Uiso 1 1 calc R . . . .
C00D C 0.3033(4) 0.4534(3) 0.8134(6) 0.0912(14) Uani 1 1 d . . . . .
H00E H 0.297404 0.411041 0.917597 0.137 Uiso 1 1 calc GR . . . .
H00F H 0.240312 0.477374 0.778062 0.137 Uiso 1 1 calc GR . . . .
H00G H 0.346029 0.500563 0.856714 0.137 Uiso 1 1 calc GR . . . .
C00E C 0.0144(5) 0.5649(4) 0.2097(8) 0.1111(18) Uani 1 1 d . . . . .
H00H H -0.024900 0.523317 0.269004 0.133 Uiso 1 1 calc R . . . .
C00F C 0.1692(5) 0.6160(4) 0.1324(8) 0.1128(19) Uani 1 1 d . . . . .
H00I H 0.236640 0.609911 0.138296 0.135 Uiso 1 1 calc R . . . .
C00G C 0.0268(6) 0.6963(5) 0.0262(9) 0.126(2) Uani 1 1 d . . . . .
H00J H -0.002950 0.743862 -0.039184 0.151 Uiso 1 1 calc R . . . .
C00H C -0.0281(5) 0.6354(5) 0.1136(10) 0.122(2) Uani 1 1 d . . . . .
H00K H -0.095603 0.641147 0.108684 0.146 Uiso 1 1 calc R . . . .
C00I C 0.1261(6) 0.6891(5) 0.0324(9) 0.134(2) Uani 1 1 d . . . . .
H00L H 0.164385 0.731298 -0.027777 0.161 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C007 1.643(4) . ?
O002 C006 1.226(4) . ?
O003 C008 1.383(5) . ?
N004 C006 1.344(5) . ?
N004 C007 1.395(5) . ?
N004 C00A 1.453(5) . ?
N005 C007 1.327(5) . ?
N005 C008 1.464(5) . ?
N005 C00D 1.457(5) . ?
C006 C008 1.518(6) . ?
C008 C009 1.519(6) . ?
C009 C00C 1.225(6) . ?
C00B C00C 1.508(7) . ?
C00B C00E 1.356(7) . ?
C00B C00F 1.370(8) . ?
C00E C00H 1.366(8) . ?
C00F C00I 1.412(8) . ?
C00G C00H 1.341(9) . ?
C00G C00I 1.368(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C006 N004 C007 111.4(4) . . ?
C006 N004 C00A 123.9(3) . . ?
C007 N004 C00A 124.7(4) . . ?
C007 N005 C008 112.8(3) . . ?
C007 N005 C00D 124.9(4) . . ?
C00D N005 C008 122.2(4) . . ?
O002 C006 N004 125.6(4) . . ?
O002 C006 C008 126.6(4) . . ?
N004 C006 C008 107.8(3) . . ?
N004 C007 S001 125.1(4) . . ?
N005 C007 S001 127.4(3) . . ?
N005 C007 N004 107.6(3) . . ?
O003 C008 N005 112.8(3) . . ?
O003 C008 C006 113.5(3) . . ?
O003 C008 C009 112.5(4) . . ?
N005 C008 C006 100.2(3) . . ?
N005 C008 C009 108.6(3) . . ?
C006 C008 C009 108.5(3) . . ?
C00C C009 C008 126.8(5) . . ?
C00E C00B C00C 118.0(6) . . ?
C00E C00B C00F 118.2(5) . . ?
C00F C00B C00C 123.7(5) . . ?
C009 C00C C00B 125.2(6) . . ?
C00B C00E C00H 121.8(7) . . ?
C00B C00F C00I 120.5(6) . . ?
C00H C00G C00I 120.6(6) . . ?
C00G C00H C00E 120.4(6) . . ?
C00G C00I C00F 118.4(7) . . ?

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
O002 C006 C008 O003 55.8(5) . . . . ?
O002 C006 C008 N005 176.3(3) . . . . ?
O002 C006 C008 C009 -70.0(5) . . . . ?
O003 C008 C009 C00C -4.4(7) . . . . ?
N004 C006 C008 O003 -125.3(3) . . . . ?
N004 C006 C008 N005 -4.8(4) . . . . ?
N004 C006 C008 C009 108.9(4) . . . . ?
N005 C008 C009 C00C -130.0(5) . . . . ?
C006 N004 C007 S001 177.7(3) . . . . ?
C006 N004 C007 N005 -2.2(4) . . . . ?
C006 C008 C009 C00C 122.0(5) . . . . ?
C007 N004 C006 O002 -176.6(3) . . . . ?
C007 N004 C006 C008 4.5(4) . . . . ?
C007 N005 C008 O003 124.6(4) . . . . ?
C007 N005 C008 C006 3.6(4) . . . . ?
C007 N005 C008 C009 -110.0(4) . . . . ?
C008 N005 C007 S001 178.9(3) . . . . ?
C008 N005 C007 N004 -1.2(4) . . . . ?
C008 C009 C00C C00B 179.1(4) . . . . ?
C00A N004 C006 O002 2.4(6) . . . . ?
C00A N004 C006 C008 -176.6(3) . . . . ?
C00A N004 C007 S001 -1.2(5) . . . . ?
C00A N004 C007 N005 178.9(3) . . . . ?
C00B C00E C00H C00G 0.2(10) . . . . ?
C00B C00F C00I C00G 0.0(9) . . . . ?
C00C C00B C00E C00H -177.6(5) . . . . ?
C00C C00B C00F C00I 177.4(5) . . . . ?
C00D N005 C007 S001 1.4(6) . . . . ?
C00D N005 C007 N004 -178.8(3) . . . . ?
C00D N005 C008 O003 -57.8(5) . . . . ?
C00D N005 C008 C006 -178.8(3) . . . . ?
C00D N005 C008 C009 67.6(5) . . . . ?
C00E C00B C00C C009 -168.5(5) . . . . ?
C00E C00B C00F C00I 0.0(8) . . . . ?
C00F C00B C00C C009 14.1(8) . . . . ?
C00F C00B C00E C00H -0.1(8) . . . . ?
C00H C00G C00I C00F 0.1(10) . . . . ?
C00I C00G C00H C00E -0.2(11) . . . . ?

_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 2.336
_oxdiff_exptl_absorpt_empirical_full_min 0.204
####################################################################### 
# 
# 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_zmc-20220314
_database_code_depnum_ccdc_archive 'CCDC 2164313'
_audit_update_record             
;
2022-04-04 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
_audit_creation_date             2022-04-03
_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         'C15 H17 Cl N2 O2 S'
_chemical_formula_sum            'C15 H17 Cl N2 O2 S'
_chemical_formula_weight         324.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N1 S1 Cl1 C1 O1'
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'
Cl Cl 0.3639 0.7018 '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                   14.5771(3)
_cell_length_b                   8.1384(2)
_cell_length_c                   14.3128(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.039(2)
_cell_angle_gamma                90
_cell_volume                     1605.10(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4462
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9330
_cell_measurement_theta_min      5.3480
_shelx_estimated_absorpt_T_max   0.729
_shelx_estimated_absorpt_T_min   0.650
_exptl_absorpt_coefficient_mu    3.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48769
_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            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7394
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.374
_diffrn_reflns_theta_min         6.316
_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 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  18.00   1.00    1.00    --  -35.62 101.00 157.00   94
  2  ω      4.00  76.00   1.00    1.00    --   35.62-101.00  53.00   72
  3  ω    101.00 177.00   1.00    1.43    --  107.12 101.00 157.00   76
  4  ω     37.00 110.00   1.00    1.43    --  107.12-101.00  53.00   73
  5  ω   -100.00 -21.00   1.00    1.00    --  -35.62 -57.00-150.00   79
  6  ω    -92.00 -35.00   1.00    1.00    --  -35.62 178.00 -90.00   57
  7  ω   -107.00 -35.00   1.00    1.00    --  -35.62-178.00-150.00   72
  8  ω     11.00  36.00   1.00    1.00    --   35.62  77.00-120.00   25
  9  ω     63.00  89.00   1.00    1.00    --   35.62 178.00-150.00   26
 10  ω     51.00  77.00   1.00    1.00    --   35.62  77.00-120.00   26
 11  ω    102.00 144.00   1.00    1.43    --  107.12 111.00  30.00   42
 12  ω     39.00 125.00   1.00    1.43    --  107.12 -45.00  60.00   86
 13  ω     56.00  95.00   1.00    1.43    --  107.12 -95.00-180.00   39
 14  ω     95.00 137.00   1.00    1.43    --  107.12  61.00   0.00   42
 15  ω    146.00 172.00   1.00    1.43    --  107.12  61.00   0.00   26
 16  ω    104.00 130.00   1.00    1.43    --  107.12 111.00  60.00   26
 17  ω     38.00 105.00   1.00    1.43    --  107.12 -95.00  90.00   67
 18  ω     89.00 171.00   1.00    1.43    --  107.12  61.00-150.00   82
 19  ω     41.00 110.00   1.00    1.43    --  107.12 -61.00-150.00   69
;
_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      -0.0281337000
_diffrn_orient_matrix_UB_12      -0.0502224000
_diffrn_orient_matrix_UB_13      0.0909164000
_diffrn_orient_matrix_UB_21      -0.0410386000
_diffrn_orient_matrix_UB_22      0.1734628000
_diffrn_orient_matrix_UB_23      0.0037428000
_diffrn_orient_matrix_UB_31      -0.1000251000
_diffrn_orient_matrix_UB_32      -0.0569605000
_diffrn_orient_matrix_UB_33      -0.0684478000
_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                2645
_reflns_number_total             3060
_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-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         0.533
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      0.997
_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)+(0.1087P)²+1.8057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1923
_refine_ls_wR_factor_ref         0.1985
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11)
2.b X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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
Cl1 Cl 1.12798(10) 0.8251(2) 0.53933(13) 0.1143(6) Uani 1 1 d . . . . .
S1 S 0.36729(5) 0.32467(10) 0.08578(6) 0.0426(3) Uani 1 1 d . . . . .
O1 O 0.67155(18) 0.3243(3) 0.06502(16) 0.0474(6) Uani 1 1 d . . . . .
H1 H 0.671922 0.417357 0.043147 0.071 Uiso 1 1 calc R U . . .
O2 O 0.65428(18) 0.1507(3) 0.28599(15) 0.0474(6) Uani 1 1 d . . . . .
H2 H 0.651670 0.055837 0.304306 0.071 Uiso 1 1 calc R U . . .
N1 N 0.55752(17) 0.4051(3) 0.14146(17) 0.0368(6) Uani 1 1 d . . . . .
N2 N 0.52985(19) 0.1395(3) 0.13171(18) 0.0382(6) Uani 1 1 d . . . . .
C1 C 0.8882(2) 0.5635(4) 0.3053(3) 0.0504(8) Uani 1 1 d . . . . .
C2 C 0.8732(3) 0.6270(5) 0.3882(3) 0.0609(10) Uani 1 1 d . . . . .
H2A H 0.812567 0.615049 0.395810 0.073 Uiso 1 1 calc R U . . .
C3 C 0.9460(3) 0.7086(6) 0.4608(4) 0.0724(12) Uani 1 1 d . . . . .
H3 H 0.934914 0.751150 0.516421 0.087 Uiso 1 1 calc R U . . .
C4 C 1.0351(3) 0.7244(5) 0.4478(4) 0.0709(12) Uani 1 1 d . . . . .
C5 C 1.0532(3) 0.6631(6) 0.3674(4) 0.0800(14) Uani 1 1 d . . . . .
H5 H 1.114268 0.674400 0.360812 0.096 Uiso 1 1 calc R U . . .
C6 C 0.9794(3) 0.5835(6) 0.2952(4) 0.0694(11) Uani 1 1 d . . . . .
H6 H 0.990887 0.542906 0.239285 0.083 Uiso 1 1 calc R U . . .
C7 C 0.8122(2) 0.4760(4) 0.2277(3) 0.0497(8) Uani 1 1 d . . . . .
H7 H 0.823019 0.459046 0.167834 0.060 Uiso 1 1 calc R U . . .
C8 C 0.7304(2) 0.4195(4) 0.2354(2) 0.0422(7) Uani 1 1 d . . . . .
H8 H 0.719736 0.434933 0.295379 0.051 Uiso 1 1 calc R U . . .
C9 C 0.6534(2) 0.3328(4) 0.1556(2) 0.0374(7) Uani 1 1 d . . . . .
C10 C 0.6354(2) 0.1530(4) 0.1829(2) 0.0378(7) Uani 1 1 d . . . . .
C11 C 0.6899(3) 0.0247(4) 0.1473(3) 0.0513(8) Uani 1 1 d . . . . .
H11 H 0.672832 0.008490 0.079468 0.062 Uiso 1 1 calc R U . . .
C12 C 0.7589(3) -0.0652(6) 0.2041(4) 0.0777(13) Uani 1 1 d . . . . .
H12A H 0.777909 -0.052311 0.272359 0.093 Uiso 1 1 calc R U . . .
H12B H 0.789558 -0.142607 0.176710 0.093 Uiso 1 1 calc R U . . .
C13 C 0.4791(3) -0.0148(4) 0.1265(2) 0.0459(7) Uani 1 1 d . . . . .
H13A H 0.411440 0.006214 0.114829 0.069 Uiso 1 1 calc R U . . .
H13B H 0.505694 -0.072921 0.187829 0.069 Uiso 1 1 calc R U . . .
H13C H 0.486417 -0.080045 0.073555 0.069 Uiso 1 1 calc R U . . .
C14 C 0.4879(2) 0.2898(4) 0.12077(19) 0.0346(6) Uani 1 1 d . . . . .
C15 C 0.5423(2) 0.5811(4) 0.1330(2) 0.0403(7) Uani 1 1 d . . . . .
H15A H 0.570221 0.624398 0.086000 0.060 Uiso 1 1 calc R U . . .
H15B H 0.572676 0.631502 0.196245 0.060 Uiso 1 1 calc R U . . .
H15C H 0.473983 0.603963 0.111270 0.060 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 C4 1.750(4) . ?
S1 C14 1.687(3) . ?
O1 H1 0.8200 . ?
O1 C9 1.406(3) . ?
O2 H2 0.8200 . ?
O2 C10 1.411(4) . ?
N1 C9 1.469(4) . ?
N1 C14 1.343(4) . ?
N1 C15 1.448(4) . ?
N2 C10 1.477(4) . ?
N2 C13 1.447(4) . ?
N2 C14 1.353(4) . ?
C1 C2 1.376(5) . ?
C1 C6 1.393(5) . ?
C1 C7 1.471(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.388(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(6) . ?
C4 C5 1.357(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.316(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.492(4) . ?
C9 C10 1.559(4) . ?
C10 C11 1.497(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.295(5) . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C9 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C14 N1 C9 111.5(2) . . ?
C14 N1 C15 126.1(3) . . ?
C15 N1 C9 121.4(2) . . ?
C13 N2 C10 121.5(2) . . ?
C14 N2 C10 110.4(2) . . ?
C14 N2 C13 125.0(3) . . ?
C2 C1 C6 118.1(4) . . ?
C2 C1 C7 122.7(3) . . ?
C6 C1 C7 119.1(4) . . ?
C1 C2 H2A 119.1 . . ?
C1 C2 C3 121.8(4) . . ?
C3 C2 H2A 119.1 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 Cl1 118.5(4) . . ?
C5 C4 Cl1 119.4(3) . . ?
C5 C4 C3 122.2(4) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.1(4) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C1 C7 H7 117.1 . . ?
C8 C7 C1 125.8(3) . . ?
C8 C7 H7 117.1 . . ?
C7 C8 H8 117.4 . . ?
C7 C8 C9 125.2(3) . . ?
C9 C8 H8 117.4 . . ?
O1 C9 N1 110.5(2) . . ?
O1 C9 C8 114.1(2) . . ?
O1 C9 C10 106.4(2) . . ?
N1 C9 C8 111.1(2) . . ?
N1 C9 C10 100.4(2) . . ?
C8 C9 C10 113.5(2) . . ?
O2 C10 N2 109.5(2) . . ?
O2 C10 C9 106.5(2) . . ?
O2 C10 C11 113.8(3) . . ?
N2 C10 C9 100.3(2) . . ?
N2 C10 C11 111.2(3) . . ?
C11 C10 C9 114.7(3) . . ?
C10 C11 H11 117.6 . . ?
C12 C11 C10 124.8(4) . . ?
C12 C11 H11 117.6 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 S1 126.0(2) . . ?
N1 C14 N2 109.0(3) . . ?
N2 C14 S1 125.1(2) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 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
Cl1 C4 C5 C6 180.0(4) . . . . ?
O1 C9 C10 O2 157.9(2) . . . . ?
O1 C9 C10 N2 -88.0(3) . . . . ?
O1 C9 C10 C11 31.2(3) . . . . ?
O2 C10 C11 C12 -10.1(5) . . . . ?
N1 C9 C10 O2 -86.9(3) . . . . ?
N1 C9 C10 N2 27.1(3) . . . . ?
N1 C9 C10 C11 146.3(3) . . . . ?
N2 C10 C11 C12 -134.2(4) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C1 C7 C8 C9 179.2(3) . . . . ?
C2 C1 C6 C5 0.9(6) . . . . ?
C2 C1 C7 C8 -14.3(6) . . . . ?
C2 C3 C4 Cl1 -179.3(3) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C6 C1 C7 C8 165.7(4) . . . . ?
C7 C1 C2 C3 179.7(4) . . . . ?
C7 C1 C6 C5 -179.1(4) . . . . ?
C7 C8 C9 O1 -4.3(5) . . . . ?
C7 C8 C9 N1 -129.9(3) . . . . ?
C7 C8 C9 C10 117.9(4) . . . . ?
C8 C9 C10 O2 31.7(3) . . . . ?
C8 C9 C10 N2 145.7(2) . . . . ?
C8 C9 C10 C11 -95.1(3) . . . . ?
C9 N1 C14 S1 -171.8(2) . . . . ?
C9 N1 C14 N2 7.7(3) . . . . ?
C9 C10 C11 C12 112.9(4) . . . . ?
C10 N2 C14 S1 -168.0(2) . . . . ?
C10 N2 C14 N1 12.5(3) . . . . ?
C13 N2 C10 O2 -74.8(3) . . . . ?
C13 N2 C10 C9 173.5(3) . . . . ?
C13 N2 C10 C11 51.7(4) . . . . ?
C13 N2 C14 S1 -7.7(4) . . . . ?
C13 N2 C14 N1 172.8(3) . . . . ?
C14 N1 C9 O1 89.4(3) . . . . ?
C14 N1 C9 C8 -143.0(2) . . . . ?
C14 N1 C9 C10 -22.7(3) . . . . ?
C14 N2 C10 O2 86.3(3) . . . . ?
C14 N2 C10 C9 -25.4(3) . . . . ?
C14 N2 C10 C11 -147.2(3) . . . . ?
C15 N1 C9 O1 -79.9(3) . . . . ?
C15 N1 C9 C8 47.8(3) . . . . ?
C15 N1 C9 C10 168.1(2) . . . . ?
C15 N1 C14 S1 -3.2(4) . . . . ?
C15 N1 C14 N2 176.3(3) . . . . ?

_olex2_date_sample_data_collection 2022-03-14
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.656
_oxdiff_exptl_absorpt_empirical_full_min 0.654
####################################################################### 
# 
# 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_zmc-20211224
_database_code_depnum_ccdc_archive 'CCDC 2131212'
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
_audit_creation_date             2021-12-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 N2 O2 S'
_chemical_formula_sum            'C13 H16 N2 O2 S'
_chemical_formula_weight         264.34
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.66580(10)
_cell_length_b                   7.56550(10)
_cell_length_c                   12.02920(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.0280(10)
_cell_angle_gamma                90
_cell_volume                     695.918(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11230
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      71.5310
_cell_measurement_theta_min      5.7710
_shelx_estimated_absorpt_T_max   0.807
_shelx_estimated_absorpt_T_min   0.777
_exptl_absorpt_coefficient_mu    2.041
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63723
_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            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15527
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.553
_diffrn_reflns_theta_min         3.684
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  18.00   1.00    1.00    --  -35.62 101.00 -13.00   94
  2  ω      4.00  76.00   1.00    1.00    --   35.62-101.00-117.00   72
  3  ω    101.00 177.00   1.00    3.64    --  107.12 101.00 -13.00   76
  4  ω     37.00 110.00   1.00    3.64    --  107.12-101.00-117.00   73
  5  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00 120.00   73
  6  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00 -90.00   88
  7  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00  60.00   73
  8  ω    -65.00  36.00   1.00    1.00    --  -35.62  19.00  60.00  101
  9  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 150.00   94
 10  ω     57.00 108.00   1.00    1.00    --   35.62 178.00  60.00   51
 11  ω     57.00 108.00   1.00    1.00    --   35.62 178.00-150.00   51
 12  ω     37.00 113.00   1.00    3.64    --  107.12-111.00  90.00   76
 13  ω     37.00 113.00   1.00    3.64    --  107.12-111.00-150.00   76
 14  ω     89.00 174.00   1.00    3.64    --  107.12  61.00  60.00   85
 15  ω     40.00 125.00   1.00    3.64    --  107.12 -61.00-150.00   85
 16  ω     89.00 174.00   1.00    3.64    --  107.12  61.00  30.00   85
 17  ω     89.00 174.00   1.00    3.64    --  107.12  61.00  90.00   85
 18  ω     90.00 176.00   1.00    3.64    --  107.12  45.00 120.00   86
 19  ω     80.00 175.00   1.00    3.64    --  107.12  77.00 -90.00   95
 20  ω     86.00 177.00   1.00    3.64    --  107.12  30.00 -30.00   91
 21  ω     38.00 110.00   1.00    3.64    --  107.12 -95.00 -30.00   72
 22  ω    100.00 177.00   1.00    3.64    --  107.12 111.00 -90.00   77
 23  ω     37.00 129.00   1.00    3.64    --  107.12 -30.00  60.00   92
 24  ω     39.00 125.00   1.00    3.64    --  107.12 -45.00 -60.00   86
 25  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00  60.00   88
 26  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00  30.00   84
 27  ω      9.00 103.00   1.00    1.00    --   35.62  77.00  60.00   94
 28  ω     57.00 108.00   1.00    1.00    --   35.62 178.00  30.00   51
 29  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-120.00   94
 30  ω     57.00 108.00   1.00    1.00    --   35.62 178.00-180.00   51
 31  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 -30.00   94
 32  ω     80.00 175.00   1.00    3.64    --  107.12  77.00   0.00   95
 33  ω     80.00 175.00   1.00    3.64    --  107.12  77.00 150.00   95
 34  ω     80.00 175.00   1.00    3.64    --  107.12  77.00-150.00   95
 35  ω     90.00 176.00   1.00    3.64    --  107.12  45.00   0.00   86
 36  ω     38.00 110.00   1.00    3.64    --  107.12 -95.00 120.00   72
 37  ω     80.00 175.00   1.00    3.64    --  107.12  77.00-120.00   95
 38  ω     86.00 177.00   1.00    3.64    --  107.12  30.00   0.00   91
 39  ω     80.00 175.00   1.00    3.64    --  107.12  77.00 -60.00   95
 40  ω     90.00 176.00   1.00    3.64    --  107.12  45.00 150.00   86
 41  ω     86.00 177.00   1.00    3.64    --  107.12  30.00  90.00   91
 42  ω     80.00 175.00   1.00    3.64    --  107.12  77.00  60.00   95
 43  ω     80.00 175.00   1.00    3.64    --  107.12  77.00-180.00   95
 44  ω     80.00 175.00   1.00    3.64    --  107.12  77.00  30.00   95
 45  ω     69.00 178.00   1.00    3.64    --  107.12  15.00-120.00  109
 46  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00 120.00   88
 47  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00 -30.00   84
 48  ω    -55.00  34.00   1.00    1.00    --  -35.62  38.00  90.00   89
 49  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00-120.00   84
 50  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00-180.00   73
 51  ω     19.00 103.00   1.00    1.00    --   35.62  57.00-150.00   84
 52  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-150.00   94
 53  ω     80.00 146.00   1.00    3.64    --  107.12  77.00 -30.00   66
 54  ω     86.00 177.00   1.00    3.64    --  107.12  30.00-120.00   91
 55  ω     86.00 177.00   1.00    3.64    --  107.12  30.00-180.00   91
 56  ω     86.00 177.00   1.00    3.64    --  107.12  30.00 -90.00   91
 57  ω     89.00 174.00   1.00    3.64    --  107.12  61.00 120.00   85
;
_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      -0.0741233000
_diffrn_orient_matrix_UB_12      0.0860317000
_diffrn_orient_matrix_UB_13      -0.1094388000
_diffrn_orient_matrix_UB_21      0.0309716000
_diffrn_orient_matrix_UB_22      -0.1732952000
_diffrn_orient_matrix_UB_23      -0.0629513000
_diffrn_orient_matrix_UB_31      -0.1847075000
_diffrn_orient_matrix_UB_32      -0.0635692000
_diffrn_orient_matrix_UB_33      0.0234212000
_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         0.838
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2640
_reflns_number_total             2687
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.104
_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)+(0.0923P)²+0.4392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1432
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 0.89869(12) 0.08601(13) 0.43677(9) 0.0296(3) Uani 1 1 d . . . . .
O1 O 0.5023(4) 0.3271(4) 0.6692(2) 0.0269(7) Uani 1 1 d . . . . .
H1 H 0.445238 0.284400 0.615582 0.040 Uiso 1 1 calc R U . . .
O2 O 0.6878(4) 0.6650(4) 0.5032(2) 0.0228(6) Uani 1 1 d . . . . .
H2 H 0.794000 0.660190 0.516856 0.034 Uiso 1 1 calc R U . . .
N1 N 0.6822(4) 0.3664(4) 0.4418(3) 0.0196(7) Uani 1 1 d . . . . .
N2 N 0.7847(5) 0.2760(4) 0.6068(3) 0.0222(7) Uani 1 1 d . . . . .
C1 C 0.7202(5) 0.6842(5) 0.9049(3) 0.0241(9) Uani 1 1 d . . . . .
C2 C 0.8546(7) 0.8046(6) 0.8914(3) 0.0310(10) Uani 1 1 d . . . . .
H2A H 0.904105 0.811785 0.823165 0.037 Uiso 1 1 calc R U . . .
C3 C 0.9154(8) 0.9134(7) 0.9777(4) 0.0425(13) Uani 1 1 d . . . . .
H3 H 1.003906 0.994412 0.966904 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8448(8) 0.9020(7) 1.0806(4) 0.0407(12) Uani 1 1 d . . . . .
H4 H 0.886274 0.974879 1.138824 0.049 Uiso 1 1 calc R U . . .
C5 C 0.7144(7) 0.7838(7) 1.0961(4) 0.0384(12) Uani 1 1 d . . . . .
H5 H 0.668436 0.775346 1.165441 0.046 Uiso 1 1 calc R U . . .
C6 C 0.6495(6) 0.6756(6) 1.0091(3) 0.0315(10) Uani 1 1 d . . . . .
H6 H 0.558834 0.597333 1.020213 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6527(5) 0.5649(6) 0.8162(3) 0.0240(8) Uani 1 1 d . . . . .
H7 H 0.549300 0.505303 0.827410 0.029 Uiso 1 1 calc R U . . .
C8 C 0.7253(5) 0.5341(5) 0.7214(3) 0.0200(8) Uani 1 1 d . . . . .
H8 H 0.828182 0.593731 0.708795 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6527(5) 0.4093(5) 0.6329(3) 0.0181(8) Uani 1 1 d . . . . .
C10 C 0.6149(5) 0.4958(5) 0.5160(3) 0.0174(7) Uani 1 1 d . . . . .
H10 H 0.487944 0.503970 0.500465 0.021 Uiso 1 1 calc R U . . .
C11 C 0.6563(7) 0.3824(7) 0.3217(3) 0.0318(10) Uani 1 1 d . . . . .
H11A H 0.535755 0.408662 0.301289 0.048 Uiso 1 1 calc R U . . .
H11B H 0.687442 0.273134 0.287570 0.048 Uiso 1 1 calc R U . . .
H11C H 0.728555 0.475820 0.296553 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8647(8) 0.1620(8) 0.6923(4) 0.0434(13) Uani 1 1 d . . . . .
H12A H 0.982550 0.200069 0.711014 0.065 Uiso 1 1 calc R U . . .
H12B H 0.865501 0.042617 0.665261 0.065 Uiso 1 1 calc R U . . .
H12C H 0.799128 0.167568 0.757305 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7875(5) 0.2470(5) 0.4967(3) 0.0182(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C13 1.679(4) . ?
O1 H1 0.8200 . ?
O1 C9 1.406(5) . ?
O2 H2 0.8200 . ?
O2 C10 1.410(5) . ?
N1 C10 1.444(5) . ?
N1 C11 1.450(5) . ?
N1 C13 1.352(5) . ?
N2 C9 1.478(5) . ?
N2 C12 1.445(5) . ?
N2 C13 1.343(5) . ?
C1 C2 1.393(6) . ?
C1 C6 1.402(6) . ?
C1 C7 1.464(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.324(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.500(5) . ?
C9 C10 1.559(5) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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
C9 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C10 N1 C11 122.0(3) . . ?
C13 N1 C10 112.2(3) . . ?
C13 N1 C11 125.3(3) . . ?
C12 N2 C9 121.2(4) . . ?
C13 N2 C9 112.3(3) . . ?
C13 N2 C12 124.6(4) . . ?
C2 C1 C6 118.0(4) . . ?
C2 C1 C7 123.0(4) . . ?
C6 C1 C7 119.0(4) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(5) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(5) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.3(5) . . ?
C5 C6 H6 119.8 . . ?
C1 C7 H7 117.0 . . ?
C8 C7 C1 126.0(4) . . ?
C8 C7 H7 117.0 . . ?
C7 C8 H8 117.8 . . ?
C7 C8 C9 124.3(4) . . ?
C9 C8 H8 117.8 . . ?
O1 C9 N2 110.7(3) . . ?
O1 C9 C8 109.2(3) . . ?
O1 C9 C10 111.2(3) . . ?
N2 C9 C8 110.8(3) . . ?
N2 C9 C10 100.4(3) . . ?
C8 C9 C10 114.3(3) . . ?
O2 C10 N1 112.8(3) . . ?
O2 C10 C9 115.4(3) . . ?
O2 C10 H10 108.5 . . ?
N1 C10 C9 102.8(3) . . ?
N1 C10 H10 108.5 . . ?
C9 C10 H10 108.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 S1 125.4(3) . . ?
N2 C13 S1 125.8(3) . . ?
N2 C13 N1 108.8(3) . . ?

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
O1 C9 C10 O2 137.4(3) . . . . ?
O1 C9 C10 N1 -99.4(4) . . . . ?
N2 C9 C10 O2 -105.4(3) . . . . ?
N2 C9 C10 N1 17.7(4) . . . . ?
C1 C2 C3 C4 1.1(8) . . . . ?
C1 C7 C8 C9 179.4(4) . . . . ?
C2 C1 C6 C5 -0.7(6) . . . . ?
C2 C1 C7 C8 11.8(7) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C3 C4 C5 C6 -0.9(8) . . . . ?
C4 C5 C6 C1 1.4(7) . . . . ?
C6 C1 C2 C3 -0.6(7) . . . . ?
C6 C1 C7 C8 -167.0(4) . . . . ?
C7 C1 C2 C3 -179.3(5) . . . . ?
C7 C1 C6 C5 178.2(4) . . . . ?
C7 C8 C9 O1 -2.5(5) . . . . ?
C7 C8 C9 N2 -124.6(4) . . . . ?
C7 C8 C9 C10 122.8(4) . . . . ?
C8 C9 C10 O2 13.2(5) . . . . ?
C8 C9 C10 N1 136.4(3) . . . . ?
C9 N2 C13 S1 -170.8(3) . . . . ?
C9 N2 C13 N1 7.6(4) . . . . ?
C10 N1 C13 S1 -175.8(3) . . . . ?
C10 N1 C13 N2 5.7(5) . . . . ?
C11 N1 C10 O2 -62.4(5) . . . . ?
C11 N1 C10 C9 172.6(4) . . . . ?
C11 N1 C13 S1 -4.1(6) . . . . ?
C11 N1 C13 N2 177.4(4) . . . . ?
C12 N2 C9 O1 -63.9(5) . . . . ?
C12 N2 C9 C8 57.4(5) . . . . ?
C12 N2 C9 C10 178.6(4) . . . . ?
C12 N2 C13 S1 -6.2(6) . . . . ?
C12 N2 C13 N1 172.3(4) . . . . ?
C13 N1 C10 O2 109.6(4) . . . . ?
C13 N1 C10 C9 -15.4(4) . . . . ?
C13 N2 C9 O1 101.3(4) . . . . ?
C13 N2 C9 C8 -137.4(3) . . . . ?
C13 N2 C9 C10 -16.2(4) . . . . ?

_olex2_date_sample_data_collection 2021-12-24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.889
_oxdiff_exptl_absorpt_empirical_full_min 0.542
