# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
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data_aigul28
_database_code_depnum_ccdc_archive 'CCDC 1587980'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2018-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
rac-1-benzyl-3-bromo-4-[(4-bromophenyl)sulfanyl]-5-hydroxy-1,5-dihydro-2H-pyrrol-2-one
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H13 Br2 N O2 S'
_chemical_formula_sum            'C17 H13 Br2 N O2 S'
_exptl_crystal_recrystallization_method 'from hot acetone solution'
_chemical_melting_point          434

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         455.16

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
_chemical_absolute_configuration ad

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_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.
;

_cell_length_a                   9.643(2)
_cell_length_b                   9.643(2)
_cell_length_c                   32.282(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2599.7(14)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4703
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      19.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    4.805
_shelx_estimated_absorpt_T_min   0.163
_shelx_estimated_absorpt_T_max   0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5236
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19163
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.439
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3138
_reflns_number_gt                2513
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'APEX3 v2015.9-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+1.8304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.19(2)
_refine_ls_number_reflns         3138
_refine_ls_number_parameters     268
_refine_ls_number_restraints     233
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.004
_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
Br1 Br 0.1677(2) 0.74642(19) 0.08809(4) 0.0859(5) Uani 1 1 d . . . . .
Br2 Br 0.2201(3) 0.4447(3) 0.36378(5) 0.1279(9) Uani 1 1 d . . . . .
S1 S 0.3370(6) 0.7677(4) 0.18472(11) 0.0827(11) Uani 1 1 d . . . . .
O2 O 0.1269(13) 0.4054(11) 0.0581(3) 0.078(3) Uani 1 1 d . . . . .
O5 O 0.4426(10) 0.5035(11) 0.1670(3) 0.067(2) Uani 1 1 d D . . . .
H5 H 0.452(15) 0.446(12) 0.184(3) 0.06(3) Uiso 1 1 d D . . . .
N1 N 0.2326(12) 0.3793(11) 0.1184(3) 0.058(2) Uani 1 1 d . . . . .
C2 C 0.1832(15) 0.4541(14) 0.0926(4) 0.062(3) Uani 1 1 d . . . . .
C3 C 0.2110(13) 0.6000(14) 0.1137(3) 0.059(3) Uani 1 1 d . . . . .
C4 C 0.2697(14) 0.6079(12) 0.1508(3) 0.053(3) Uani 1 1 d . . . . .
C5 C 0.2866(13) 0.4618(13) 0.1584(3) 0.053(3) Uani 1 1 d . . . . .
H50 H 0.215112 0.396073 0.180739 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2298(15) 0.2313(15) 0.1104(4) 0.063(3) Uani 1 1 d D U . . .
H6A H 0.326133 0.238171 0.121788 0.075 Uiso 0.52(5) 1 calc R U P A 1
H6B H 0.231386 0.217378 0.080683 0.075 Uiso 0.52(5) 1 calc R U P A 1
H6C H 0.323914 0.236910 0.122925 0.075 Uiso 0.48(5) 1 calc R U P A 2
H6D H 0.237304 0.220740 0.080726 0.075 Uiso 0.48(5) 1 calc R U P A 2
C7 C 0.087(3) 0.087(6) 0.1282(16) 0.053(7) Uani 0.52(5) 1 d D U P A 1
C8 C -0.064(3) 0.042(4) 0.1145(11) 0.064(7) Uani 0.52(5) 1 d D U P A 1
H8 H -0.080619 0.101787 0.094574 0.077 Uiso 0.52(5) 1 calc R U P A 1
C9 C -0.190(3) -0.092(4) 0.1308(13) 0.072(8) Uani 0.52(5) 1 d D U P A 1
H9 H -0.293769 -0.117202 0.124232 0.086 Uiso 0.52(5) 1 calc R U P A 1
C10 C -0.167(4) -0.190(5) 0.1566(14) 0.070(9) Uani 0.52(5) 1 d D U P A 1
H10 H -0.252130 -0.288380 0.164945 0.084 Uiso 0.52(5) 1 calc R U P A 1
C11 C -0.016(3) -0.142(3) 0.1698(11) 0.064(7) Uani 0.52(5) 1 d D U P A 1
H11 H 0.000507 -0.204518 0.188888 0.077 Uiso 0.52(5) 1 calc R U P A 1
C12 C 0.113(3) -0.004(3) 0.1562(10) 0.059(7) Uani 0.52(5) 1 d D U P A 1
H12 H 0.215572 0.027010 0.165695 0.071 Uiso 0.52(5) 1 calc R U P A 1
C19 C 0.084(4) 0.083(6) 0.1262(15) 0.055(8) Uani 0.48(5) 1 d D U P A 2
C20 C -0.056(3) -0.001(4) 0.1039(10) 0.069(8) Uani 0.48(5) 1 d D U P A 2
H20 H -0.060772 0.032735 0.077212 0.082 Uiso 0.48(5) 1 calc R U P A 2
C21 C -0.186(4) -0.131(4) 0.1198(10) 0.067(7) Uani 0.48(5) 1 d D U P A 2
H21 H -0.275721 -0.189954 0.103145 0.081 Uiso 0.48(5) 1 calc R U P A 2
C22 C -0.188(4) -0.178(6) 0.1598(13) 0.072(9) Uani 0.48(5) 1 d D U P A 2
H22 H -0.281629 -0.257404 0.172138 0.086 Uiso 0.48(5) 1 calc R U P A 2
C23 C -0.047(4) -0.102(4) 0.1806(10) 0.070(8) Uani 0.48(5) 1 d D U P A 2
H23 H -0.040764 -0.140803 0.206504 0.084 Uiso 0.48(5) 1 calc R U P A 2
C24 C 0.085(4) 0.027(4) 0.1652(9) 0.061(8) Uani 0.48(5) 1 d D U P A 2
H24 H 0.177372 0.078865 0.181275 0.074 Uiso 0.48(5) 1 calc R U P A 2
C13 C 0.3075(15) 0.6744(15) 0.2338(3) 0.061(3) Uani 1 1 d . . . . .
C14 C 0.1558(19) 0.577(2) 0.2481(4) 0.085(4) Uani 1 1 d . . . . .
H14 H 0.069525 0.557635 0.231393 0.102 Uiso 1 1 calc R U . . .
C15 C 0.1270(18) 0.506(2) 0.2861(5) 0.094(5) Uani 1 1 d . . . . .
H15 H 0.023273 0.436471 0.295146 0.113 Uiso 1 1 calc R U . . .
C16 C 0.2580(19) 0.5413(19) 0.3106(4) 0.075(4) Uani 1 1 d . . . . .
C17 C 0.409(2) 0.641(2) 0.2982(5) 0.089(4) Uani 1 1 d . . . . .
H17 H 0.494769 0.665218 0.315511 0.106 Uiso 1 1 calc R U . . .
C18 C 0.4337(17) 0.7087(17) 0.2588(4) 0.082(4) Uani 1 1 d . . . . .
H18 H 0.537335 0.777528 0.249567 0.099 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
Br1 C3 1.855(12) . ?
Br2 C16 1.901(13) . ?
S1 C4 1.730(11) . ?
S1 C13 1.774(11) . ?
O2 C2 1.225(14) . ?
O5 C5 1.377(14) . ?
O5 H5 0.81(3) . ?
N1 C2 1.337(15) . ?
N1 C6 1.438(15) . ?
N1 C5 1.467(14) . ?
C2 C3 1.462(18) . ?
C3 C4 1.311(14) . ?
C4 C5 1.517(16) . ?
C5 H50 0.9800 . ?
C6 C7 1.49(2) . ?
C6 C19 1.51(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C6 H6D 0.9700 . ?
C7 C12 1.37(2) . ?
C7 C8 1.37(2) . ?
C8 C9 1.36(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.36(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.36(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.36(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C19 C24 1.37(2) . ?
C19 C20 1.37(2) . ?
C20 C21 1.36(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.36(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.36(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.36(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C13 C18 1.354(17) . ?
C13 C14 1.36(2) . ?
C14 C15 1.36(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.38(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.34(2) . ?
C17 C18 1.39(2) . ?
C17 H17 0.9300 . ?
C18 H18 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
C4 S1 C13 102.7(5) . . ?
C5 O5 H5 115(9) . . ?
C2 N1 C6 126.1(10) . . ?
C2 N1 C5 112.4(10) . . ?
C6 N1 C5 121.5(10) . . ?
O2 C2 N1 124.7(12) . . ?
O2 C2 C3 128.7(11) . . ?
N1 C2 C3 106.6(10) . . ?
C4 C3 C2 110.4(11) . . ?
C4 C3 Br1 128.2(10) . . ?
C2 C3 Br1 121.5(8) . . ?
C3 C4 C5 109.7(10) . . ?
C3 C4 S1 126.1(9) . . ?
C5 C4 S1 124.0(8) . . ?
O5 C5 N1 112.1(10) . . ?
O5 C5 C4 111.7(9) . . ?
N1 C5 C4 100.8(8) . . ?
O5 C5 H50 110.6 . . ?
N1 C5 H50 110.6 . . ?
C4 C5 H50 110.6 . . ?
N1 C6 C7 114(3) . . ?
N1 C6 C19 115(3) . . ?
N1 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N1 C6 H6C 108.5 . . ?
C19 C6 H6C 108.5 . . ?
N1 C6 H6D 108.5 . . ?
C19 C6 H6D 108.5 . . ?
H6C C6 H6D 107.5 . . ?
C12 C7 C8 120.8(19) . . ?
C12 C7 C6 118(2) . . ?
C8 C7 C6 120.7(19) . . ?
C9 C8 C7 119(2) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 121(2) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 118(2) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C11 C12 122(2) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C7 118(2) . . ?
C11 C12 H12 120.9 . . ?
C7 C12 H12 120.9 . . ?
C24 C19 C20 117(2) . . ?
C24 C19 C6 119(2) . . ?
C20 C19 C6 124(2) . . ?
C21 C20 C19 122(2) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 121(2) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 116(2) . . ?
C23 C22 H22 121.8 . . ?
C21 C22 H22 121.8 . . ?
C24 C23 C22 123(2) . . ?
C24 C23 H23 118.6 . . ?
C22 C23 H23 118.6 . . ?
C23 C24 C19 120(2) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C18 C13 C14 119.3(12) . . ?
C18 C13 S1 120.7(10) . . ?
C14 C13 S1 119.8(10) . . ?
C15 C14 C13 122.0(13) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 117.3(14) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
C17 C16 C15 122.4(14) . . ?
C17 C16 Br2 119.7(11) . . ?
C15 C16 Br2 117.9(12) . . ?
C16 C17 C18 118.7(14) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C13 C18 C17 120.3(14) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?

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
C6 N1 C2 O2 1(2) . . . . ?
C5 N1 C2 O2 -177.0(12) . . . . ?
C6 N1 C2 C3 -179.2(11) . . . . ?
C5 N1 C2 C3 3.3(13) . . . . ?
O2 C2 C3 C4 178.5(13) . . . . ?
N1 C2 C3 C4 -1.8(14) . . . . ?
O2 C2 C3 Br1 -2.4(19) . . . . ?
N1 C2 C3 Br1 177.3(8) . . . . ?
C2 C3 C4 C5 -0.3(14) . . . . ?
Br1 C3 C4 C5 -179.3(8) . . . . ?
C2 C3 C4 S1 173.9(10) . . . . ?
Br1 C3 C4 S1 -5.1(17) . . . . ?
C13 S1 C4 C3 153.0(11) . . . . ?
C13 S1 C4 C5 -33.6(11) . . . . ?
C2 N1 C5 O5 -122.2(11) . . . . ?
C6 N1 C5 O5 60.1(14) . . . . ?
C2 N1 C5 C4 -3.3(12) . . . . ?
C6 N1 C5 C4 179.0(11) . . . . ?
C3 C4 C5 O5 121.3(11) . . . . ?
S1 C4 C5 O5 -53.1(13) . . . . ?
C3 C4 C5 N1 2.1(12) . . . . ?
S1 C4 C5 N1 -172.3(9) . . . . ?
C2 N1 C6 C7 -97(2) . . . . ?
C5 N1 C6 C7 80(2) . . . . ?
C2 N1 C6 C19 -94.4(18) . . . . ?
C5 N1 C6 C19 83.0(18) . . . . ?
N1 C6 C7 C12 -120(5) . . . . ?
N1 C6 C7 C8 64(6) . . . . ?
C12 C7 C8 C9 3(8) . . . . ?
C6 C7 C8 C9 178(4) . . . . ?
C7 C8 C9 C10 -7(7) . . . . ?
C8 C9 C10 C11 8(7) . . . . ?
C9 C10 C11 C12 -4(6) . . . . ?
C10 C11 C12 C7 0(6) . . . . ?
C8 C7 C12 C11 1(8) . . . . ?
C6 C7 C12 C11 -175(4) . . . . ?
N1 C6 C19 C24 -91(6) . . . . ?
N1 C6 C19 C20 88(7) . . . . ?
C24 C19 C20 C21 0(9) . . . . ?
C6 C19 C20 C21 -178(5) . . . . ?
C19 C20 C21 C22 5(7) . . . . ?
C20 C21 C22 C23 -9(8) . . . . ?
C21 C22 C23 C24 9(8) . . . . ?
C22 C23 C24 C19 -4(8) . . . . ?
C20 C19 C24 C23 -1(9) . . . . ?
C6 C19 C24 C23 177(4) . . . . ?
C4 S1 C13 C18 116.3(12) . . . . ?
C4 S1 C13 C14 -68.8(12) . . . . ?
C18 C13 C14 C15 -3(2) . . . . ?
S1 C13 C14 C15 -178.1(14) . . . . ?
C13 C14 C15 C16 2(3) . . . . ?
C14 C15 C16 C17 0(3) . . . . ?
C14 C15 C16 Br2 179.6(13) . . . . ?
C15 C16 C17 C18 -2(3) . . . . ?
Br2 C16 C17 C18 179.0(13) . . . . ?
C14 C13 C18 C17 2(2) . . . . ?
S1 C13 C18 C17 176.6(12) . . . . ?
C16 C17 C18 C13 1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O2 0.81(3) 1.96(5) 2.745(12) 163(13) 5 yes

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_aigul22
_database_code_depnum_ccdc_archive 'CCDC 1587983'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2018-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
rac-1-benzyl-3-bromo-4-[(4-bromophenyl)sulfanyl]-5-hydroxy-1,5-dihydro-2H-pyrrol-2-one
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H13 Br2 N O2 S'
_chemical_formula_sum            'C17 H13 Br2 N O2 S'
_exptl_crystal_recrystallization_method 'from hot acetone solution'
_chemical_melting_point          419

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         455.16

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_chemical_absolute_configuration ad

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

_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.
;

_cell_length_a                   9.071(3)
_cell_length_b                   8.725(3)
_cell_length_c                   11.441(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.448(4)
_cell_angle_gamma                90
_cell_volume                     836.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2940
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.558
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    4.976
_shelx_estimated_absorpt_T_min   0.168
_shelx_estimated_absorpt_T_max   0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2235
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6344
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.429
_diffrn_reflns_theta_max         25.850
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3183
_reflns_number_gt                2800
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.975

_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       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'APEX3 v2015.9-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0747P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1122 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(16)
_refine_ls_number_reflns         3183
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Br1 Br 0.70123(9) 0.56071(10) 0.36050(7) 0.0438(3) Uani 1 1 d . . . . .
Br2 Br 0.10953(11) 0.18145(13) 0.03941(9) 0.0584(3) Uani 1 1 d . . . . .
S1 S 0.6115(3) 0.3209(3) 0.5998(2) 0.0453(6) Uani 1 1 d . . . . .
O2 O 1.0808(6) 0.5662(9) 0.5117(5) 0.0445(13) Uani 1 1 d . . . . .
O5 O 0.9669(7) 0.1931(7) 0.7276(5) 0.0406(13) Uani 1 1 d . . . . .
N1 N 1.0635(7) 0.4256(8) 0.6753(6) 0.0356(15) Uani 1 1 d . . . . .
C2 C 1.0045(9) 0.4953(9) 0.5630(7) 0.0316(16) Uani 1 1 d . . . . .
C3 C 0.8290(9) 0.4713(8) 0.5137(7) 0.0305(16) Uani 1 1 d . . . . .
C4 C 0.7883(9) 0.3911(9) 0.5947(7) 0.0323(17) Uani 1 1 d . . . . .
C5 C 0.9414(9) 0.3496(9) 0.7066(8) 0.0337(17) Uani 1 1 d . . . . .
H5A H 0.937753 0.396849 0.783149 0.040 Uiso 1 1 calc R U . . .
C6 C 1.2287(9) 0.4308(10) 0.7619(7) 0.0356(17) Uani 1 1 d . . . . .
H6A H 1.295792 0.446848 0.714290 0.043 Uiso 1 1 calc R U . . .
H6B H 1.257427 0.332924 0.804862 0.043 Uiso 1 1 calc R U . . .
C7 C 1.2603(8) 0.5568(12) 0.8595(7) 0.0339(16) Uani 1 1 d . . . . .
C8 C 1.3243(11) 0.5222(11) 0.9870(8) 0.047(2) Uani 1 1 d . . . . .
H8 H 1.351160 0.421496 1.012981 0.057 Uiso 1 1 calc R U . . .
C9 C 1.3488(12) 0.6373(13) 1.0769(9) 0.061(3) Uani 1 1 d . . . . .
H9 H 1.387150 0.612441 1.162421 0.073 Uiso 1 1 calc R U . . .
C10 C 1.3167(12) 0.7870(14) 1.0399(11) 0.059(3) Uani 1 1 d . . . . .
H10 H 1.335214 0.864285 1.099805 0.071 Uiso 1 1 calc R U . . .
C11 C 1.2576(13) 0.8212(11) 0.9148(11) 0.054(2) Uani 1 1 d . . . . .
H11 H 1.236745 0.922872 0.889586 0.065 Uiso 1 1 calc R U . . .
C12 C 1.2278(11) 0.7084(11) 0.8241(9) 0.045(2) Uani 1 1 d . . . . .
H12 H 1.185627 0.734479 0.738855 0.054 Uiso 1 1 calc R U . . .
C13 C 0.4810(9) 0.2977(10) 0.4398(7) 0.0360(17) Uani 1 1 d . . . . .
C14 C 0.5255(9) 0.2134(10) 0.3570(8) 0.0397(19) Uani 1 1 d . . . . .
H14 H 0.629403 0.176940 0.381843 0.048 Uiso 1 1 calc R U . . .
C15 C 0.4150(9) 0.1828(11) 0.2363(8) 0.0416(19) Uani 1 1 d . . . . .
H15 H 0.445706 0.128562 0.179315 0.050 Uiso 1 1 calc R U . . .
C16 C 0.2603(10) 0.2324(10) 0.2007(8) 0.0407(19) Uani 1 1 d . . . . .
C17 C 0.2158(10) 0.3198(12) 0.2833(9) 0.051(2) Uani 1 1 d . . . . .
H17 H 0.111538 0.355262 0.258193 0.061 Uiso 1 1 calc R U . . .
C18 C 0.3254(10) 0.3543(12) 0.4021(9) 0.046(2) Uani 1 1 d . . . . .
H18 H 0.296288 0.414599 0.456817 0.055 Uiso 1 1 calc R U . . .
H5 H 0.979(11) 0.146(12) 0.664(10) 0.05(3) Uiso 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
Br1 C3 1.864(7) . ?
Br2 C16 1.884(8) . ?
S1 C4 1.738(8) . ?
S1 C13 1.771(8) . ?
O2 C2 1.231(9) . ?
O5 C5 1.390(10) . ?
O5 H5 0.87(11) . ?
N1 C2 1.335(10) . ?
N1 C6 1.447(9) . ?
N1 C5 1.449(10) . ?
C2 C3 1.487(10) . ?
C3 C4 1.322(10) . ?
C4 C5 1.530(11) . ?
C5 H5A 0.9800 . ?
C6 C7 1.514(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.381(11) . ?
C7 C12 1.382(14) . ?
C8 C9 1.394(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(16) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(16) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(14) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.377(12) . ?
C13 C18 1.399(11) . ?
C14 C15 1.388(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(13) . ?
C17 C18 1.376(13) . ?
C17 H17 0.9300 . ?
C18 H18 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
C4 S1 C13 105.5(4) . . ?
C5 O5 H5 112(7) . . ?
C2 N1 C6 125.1(7) . . ?
C2 N1 C5 112.5(6) . . ?
C6 N1 C5 122.3(7) . . ?
O2 C2 N1 126.6(7) . . ?
O2 C2 C3 127.2(7) . . ?
N1 C2 C3 106.2(7) . . ?
C4 C3 C2 110.8(7) . . ?
C4 C3 Br1 129.9(6) . . ?
C2 C3 Br1 119.3(5) . . ?
C3 C4 C5 107.7(7) . . ?
C3 C4 S1 135.9(6) . . ?
C5 C4 S1 116.3(6) . . ?
O5 C5 N1 113.6(7) . . ?
O5 C5 C4 114.5(6) . . ?
N1 C5 C4 102.7(6) . . ?
O5 C5 H5A 108.6 . . ?
N1 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
N1 C6 C7 112.5(6) . . ?
N1 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C12 118.4(8) . . ?
C8 C7 C6 120.3(9) . . ?
C12 C7 C6 121.3(7) . . ?
C7 C8 C9 120.4(9) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.2(10) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.2(10) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.5(10) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C7 120.2(9) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C14 C13 C18 120.2(8) . . ?
C14 C13 S1 121.1(6) . . ?
C18 C13 S1 118.4(6) . . ?
C13 C14 C15 119.8(7) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.2(8) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.1(8) . . ?
C15 C16 Br2 119.6(7) . . ?
C17 C16 Br2 120.3(6) . . ?
C18 C17 C16 120.2(7) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 119.4(8) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?

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
C6 N1 C2 O2 4.8(13) . . . . ?
C5 N1 C2 O2 -178.8(8) . . . . ?
C6 N1 C2 C3 -174.5(7) . . . . ?
C5 N1 C2 C3 1.9(9) . . . . ?
O2 C2 C3 C4 -179.2(8) . . . . ?
N1 C2 C3 C4 0.2(9) . . . . ?
O2 C2 C3 Br1 -2.3(11) . . . . ?
N1 C2 C3 Br1 177.0(5) . . . . ?
C2 C3 C4 C5 -2.0(9) . . . . ?
Br1 C3 C4 C5 -178.4(6) . . . . ?
C2 C3 C4 S1 -179.3(7) . . . . ?
Br1 C3 C4 S1 4.3(13) . . . . ?
C13 S1 C4 C3 26.4(10) . . . . ?
C13 S1 C4 C5 -150.8(6) . . . . ?
C2 N1 C5 O5 121.3(8) . . . . ?
C6 N1 C5 O5 -62.2(10) . . . . ?
C2 N1 C5 C4 -3.0(9) . . . . ?
C6 N1 C5 C4 173.5(7) . . . . ?
C3 C4 C5 O5 -120.7(8) . . . . ?
S1 C4 C5 O5 57.2(8) . . . . ?
C3 C4 C5 N1 2.9(8) . . . . ?
S1 C4 C5 N1 -179.1(5) . . . . ?
C2 N1 C6 C7 94.0(9) . . . . ?
C5 N1 C6 C7 -82.1(10) . . . . ?
N1 C6 C7 C8 122.7(8) . . . . ?
N1 C6 C7 C12 -58.0(10) . . . . ?
C12 C7 C8 C9 2.6(13) . . . . ?
C6 C7 C8 C9 -178.0(8) . . . . ?
C7 C8 C9 C10 -3.1(16) . . . . ?
C8 C9 C10 C11 1.4(16) . . . . ?
C9 C10 C11 C12 0.6(16) . . . . ?
C10 C11 C12 C7 -1.0(15) . . . . ?
C8 C7 C12 C11 -0.6(13) . . . . ?
C6 C7 C12 C11 -180.0(8) . . . . ?
C4 S1 C13 C14 53.6(8) . . . . ?
C4 S1 C13 C18 -132.6(7) . . . . ?
C18 C13 C14 C15 -0.8(13) . . . . ?
S1 C13 C14 C15 172.8(7) . . . . ?
C13 C14 C15 C16 -2.0(14) . . . . ?
C14 C15 C16 C17 3.2(14) . . . . ?
C14 C15 C16 Br2 -177.0(7) . . . . ?
C15 C16 C17 C18 -1.5(15) . . . . ?
Br2 C16 C17 C18 178.7(8) . . . . ?
C16 C17 C18 C13 -1.3(15) . . . . ?
C14 C13 C18 C17 2.5(14) . . . . ?
S1 C13 C18 C17 -171.4(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O2 0.87(11) 2.00(11) 2.830(8) 158(9) 2_746 yes

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.087

