# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

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

data_exp_211
_database_code_depnum_ccdc_archive 'CCDC 1868563'
_audit_update_record             
;
2018-09-19 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
_audit_creation_date             2018-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N O2 S'
_chemical_formula_sum            'C12 H11 N O2 S'
_chemical_formula_weight         233.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.1231(2)
_cell_length_b                   11.9525(2)
_cell_length_c                   8.55770(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.993(2)
_cell_angle_gamma                90
_cell_volume                     1120.48(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7303
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4810
_cell_measurement_theta_min      5.4680
_shelx_estimated_absorpt_T_max   0.449
_shelx_estimated_absorpt_T_min   0.363
_exptl_absorpt_coefficient_mu    2.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.39
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9783
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         5.478
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -35.00   1.00    1.00    --    0.00 -38.00-180.00   54
  2  ω    -63.00 -37.00   1.00    1.00    --    0.00 -38.00 120.00   26
  3  ω    -83.00   0.00   1.00    1.00    --    0.00 -38.00 -90.00   83
  4  ω    -17.00  18.00   1.00    1.00    --    0.00  38.00 120.00   35
  5  ω     36.00  62.00   1.00    1.00    --    0.00  38.00 120.00   26
  6  ω    -23.00  18.00   1.00    1.00    --    0.00 -38.00-180.00   41
  7  ω    -16.00   9.00   1.00    1.00    --    0.00 -38.00 120.00   25
  8  ω     76.00 158.00   1.00    1.00    --   95.80  30.00  30.00   82
  9  ω     41.00 101.00   1.00    1.00    --   95.80 -61.00 -90.00   60
 10  ω     15.00 107.00   1.00    1.00    --   95.80 -61.00-180.00   92
 11  ω      6.00 115.00   1.00    1.00    --   95.80 -15.00  30.00  109
 12  ω     93.00 119.00   1.00    1.00    --   95.80 -82.00 -30.00   26
 13  ω     19.00 120.00   1.00    1.00    --   95.80 -61.00  30.00  101
 14  ω     23.00 117.00   1.00    1.00    --   95.80 -82.00-180.00   94
 15  ω     60.00 103.00   1.00    1.00    --   95.80 -82.00 120.00   43
 16  ω     44.00 114.00   1.00    1.00    --   95.80 -82.00 -90.00   70
 17  ω     85.00 185.00   1.00    1.00    --   95.80  30.00   0.00  100
 18  ω     13.00  39.00   1.00    1.00    --   95.80 -82.00 -30.00   26
 19  ω     31.00 126.00   1.00    1.00    --   95.80 -82.00  30.00   95
 20  ω     69.00 175.00   1.00    1.00    --   95.80  15.00 -60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0330021000
_diffrn_orient_matrix_UB_12      -0.1252082000
_diffrn_orient_matrix_UB_13      0.0127231000
_diffrn_orient_matrix_UB_21      -0.1200768000
_diffrn_orient_matrix_UB_22      -0.0283751000
_diffrn_orient_matrix_UB_23      -0.1119992000
_diffrn_orient_matrix_UB_31      0.0653852000
_diffrn_orient_matrix_UB_32      0.0110257000
_diffrn_orient_matrix_UB_33      -0.1439289000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1824
_reflns_number_total             1960
_reflns_odcompleteness_completeness 99.81
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.408
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.033(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1960
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.041
_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)+(0.0690P)²+0.2420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1078
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_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 0.83082(4) 0.38960(3) 0.55548(4) 0.0420(2) Uani 1 1 d . . . . .
O1 O 0.86675(12) 0.49980(11) 0.60912(14) 0.0522(4) Uani 1 1 d . . . . .
O2 O 0.83564(15) 0.30396(14) 0.67256(18) 0.0708(5) Uani 1 1 d . . . . .
N1 N 0.91655(13) 0.35494(14) 0.43223(19) 0.0499(4) Uani 1 1 d . . . . .
H1A H 0.956046 0.292790 0.443854 0.060 Uiso 1 1 calc R . . . .
H1B H 0.923283 0.398399 0.354117 0.060 Uiso 1 1 calc R . . . .
C00C C 0.47237(19) 0.32202(19) 0.4475(3) 0.0642(6) Uani 1 1 d . . . . .
H00C H 0.416771 0.280199 0.492715 0.077 Uiso 1 1 calc R . . . .
C1 C 0.67677(15) 0.38979(13) 0.45312(19) 0.0409(4) Uani 1 1 d . . . . .
C2 C 0.59352(19) 0.32826(16) 0.5222(2) 0.0541(5) Uani 1 1 d . . . . .
H2 H 0.618898 0.291456 0.618014 0.065 Uiso 1 1 calc R . . . .
C3 C 0.43498(19) 0.37703(19) 0.3083(3) 0.0648(6) Uani 1 1 d . . . . .
H3 H 0.353711 0.373307 0.259003 0.078 Uiso 1 1 calc R . . . .
C4 C 0.51762(17) 0.43837(17) 0.2402(2) 0.0563(5) Uani 1 1 d . . . . .
H4 H 0.490557 0.475471 0.145116 0.068 Uiso 1 1 calc R . . . .
C5 C 0.64084(15) 0.44645(14) 0.30994(19) 0.0412(4) Uani 1 1 d . . . . .
C6 C 0.72399(14) 0.51113(14) 0.22447(18) 0.0407(4) Uani 1 1 d . . . . .
C7 C 0.77254(18) 0.61381(15) 0.2778(2) 0.0504(5) Uani 1 1 d . . . . .
H7 H 0.755714 0.643198 0.372291 0.061 Uiso 1 1 calc R . . . .
C8 C 0.8457(2) 0.67301(18) 0.1919(2) 0.0587(5) Uani 1 1 d . . . . .
H8 H 0.876478 0.742452 0.228063 0.070 Uiso 1 1 calc R . . . .
C9 C 0.87340(19) 0.63010(19) 0.0537(2) 0.0589(5) Uani 1 1 d . . . . .
H9 H 0.923364 0.669877 -0.003084 0.071 Uiso 1 1 calc R . . . .
C10 C 0.8265(2) 0.5273(2) -0.0006(2) 0.0616(5) Uani 1 1 d . . . . .
H10 H 0.845960 0.497373 -0.093371 0.074 Uiso 1 1 calc R . . . .
C11 C 0.75110(19) 0.46924(16) 0.0825(2) 0.0520(5) Uani 1 1 d . . . . .
H11 H 0.717893 0.401282 0.043509 0.062 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
S1 O1 1.4289(13) . ?
S1 O2 1.4268(14) . ?
S1 N1 1.5945(16) . ?
S1 C1 1.7840(17) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C00C H00C 0.9300 . ?
C00C C2 1.390(3) . ?
C00C C3 1.361(3) . ?
C1 C2 1.392(2) . ?
C1 C5 1.396(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(3) . ?
C5 C6 1.491(2) . ?
C6 C7 1.386(2) . ?
C6 C11 1.394(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 106.62(8) . . ?
O1 S1 C1 110.35(8) . . ?
O2 S1 O1 117.48(9) . . ?
O2 S1 N1 108.92(10) . . ?
O2 S1 C1 105.16(8) . . ?
N1 S1 C1 108.01(8) . . ?
S1 N1 H1A 120.0 . . ?
S1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C2 C00C H00C 120.0 . . ?
C3 C00C H00C 120.0 . . ?
C3 C00C C2 120.09(19) . . ?
C2 C1 S1 116.34(14) . . ?
C2 C1 C5 121.25(17) . . ?
C5 C1 S1 122.40(13) . . ?
C00C C2 C1 119.76(19) . . ?
C00C C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C00C C3 H3 120.0 . . ?
C00C C3 C4 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.07(19) . . ?
C5 C4 H4 119.0 . . ?
C1 C5 C4 116.77(16) . . ?
C1 C5 C6 125.07(15) . . ?
C4 C5 C6 118.13(15) . . ?
C7 C6 C5 122.49(15) . . ?
C7 C6 C11 118.30(16) . . ?
C11 C6 C5 119.17(16) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.66(18) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.60(19) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.12(18) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.78(18) . . ?
C10 C11 H11 119.6 . . ?

_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 1.838
_oxdiff_exptl_absorpt_empirical_full_min 0.523
