# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_pbr
_database_code_depnum_ccdc_archive 'CCDC 1434764'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'University of Hyderabad'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Cl N O2 S'
_chemical_formula_weight         397.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I a'
_symmetry_space_group_name_Hall  'I -2ya'

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

_cell_length_a                   11.4861(4)
_cell_length_b                   14.0594(4)
_cell_length_c                   13.4860(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.393(4)
_cell_angle_gamma                90.00
_cell_volume                     2027.76(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       round
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    2.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.354
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'

_exptl_special_details           
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.37.30a (release 13-01-2014 CrysAlis171 .NET)
(compiled Jan 13 2014,18:40:09)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3532
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.72
_diffrn_reflns_theta_max         71.77
_reflns_number_total             2273
_reflns_number_gt                2237
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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     
'calc w=1/[σ²(Fo²)+(0.1169P)²+0.6849P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.59(2)
_refine_ls_number_reflns         2273
_refine_ls_number_parameters     245
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.58383(7) 0.20902(6) 0.49254(6) 0.0376(2) Uani 1 1 d . . .
Cl2 Cl 0.25434(11) 0.23642(10) 0.38778(13) 0.0702(4) Uani 1 1 d . . .
O1 O 0.5755(3) 0.2177(2) 0.5966(2) 0.0500(7) Uani 1 1 d . . .
O2 O 0.6998(3) 0.2229(2) 0.4801(3) 0.0543(8) Uani 1 1 d . . .
N3 N 0.4889(3) 0.2916(2) 0.4191(3) 0.0394(7) Uani 1 1 d . . .
C4 C 0.4519(4) 0.0454(3) 0.4839(3) 0.0443(8) Uani 1 1 d . . .
H4 H 0.4325 0.0701 0.5400 0.053 Uiso 1 1 calc R . .
C5 C 0.4774(5) 0.2977(3) 0.3056(3) 0.0511(10) Uani 1 1 d . . .
H5A H 0.4133 0.2540 0.2630 0.061 Uiso 1 1 calc R . .
H5B H 0.5560 0.2796 0.2994 0.061 Uiso 1 1 calc R . .
C6 C 0.5258(3) 0.0967(3) 0.4419(3) 0.0382(7) Uani 1 1 d . . .
C7 C 0.5548(4) 0.0606(3) 0.3580(4) 0.0446(8) Uani 1 1 d . . .
H7 H 0.6049 0.0951 0.3301 0.053 Uiso 1 1 calc R . .
C8 C 0.4439(4) 0.3970(3) 0.2655(3) 0.0410(8) Uani 1 1 d . . .
C9 C 0.3814(4) 0.3164(3) 0.4402(3) 0.0419(8) Uani 1 1 d . . .
C10 C 0.4343(4) -0.0797(3) 0.3580(3) 0.0460(9) Uani 1 1 d . . .
C11 C 0.4071(4) -0.0427(3) 0.4420(4) 0.0489(10) Uani 1 1 d . . .
H11 H 0.3580 -0.0775 0.4706 0.059 Uiso 1 1 calc R . .
C12 C 0.3640(4) 0.3968(3) 0.4829(4) 0.0483(9) Uani 1 1 d . . .
H12 H 0.2853 0.4051 0.4865 0.058 Uiso 1 1 calc R . .
C13 C 0.4525(4) 0.4745(3) 0.5253(3) 0.0434(9) Uani 1 1 d . . .
C14 C 0.5327(5) 0.4670(4) 0.2906(4) 0.0585(11) Uani 1 1 d . . .
H14 H 0.6158 0.4522 0.3296 0.070 Uiso 1 1 calc R . .
C15 C 0.6568(5) 0.5404(4) 0.6168(4) 0.0576(11) Uani 1 1 d . . .
H15 H 0.7420 0.5310 0.6530 0.069 Uiso 1 1 calc R . .
C16 C 0.4818(6) 0.6449(4) 0.5514(4) 0.0653(13) Uani 1 1 d . . .
H16 H 0.4481 0.7059 0.5417 0.078 Uiso 1 1 calc R . .
C17 C 0.5808(4) 0.4628(3) 0.5783(3) 0.0486(9) Uani 1 1 d . . .
H17 H 0.6153 0.4021 0.5878 0.058 Uiso 1 1 calc R . .
C18 C 0.6094(6) 0.6323(4) 0.6027(4) 0.0620(12) Uani 1 1 d . . .
H18 H 0.6622 0.6843 0.6272 0.074 Uiso 1 1 calc R . .
C19 C 0.4042(5) 0.5671(4) 0.5147(4) 0.0532(10) Uani 1 1 d . . .
H19 H 0.3184 0.5765 0.4823 0.064 Uiso 1 1 calc R . .
C20 C 0.5081(5) -0.0275(3) 0.3164(4) 0.0510(10) Uani 1 1 d . . .
H20 H 0.5266 -0.0519 0.2598 0.061 Uiso 1 1 calc R . .
C21 C 0.3221(5) 0.4214(4) 0.2081(4) 0.0636(13) Uani 1 1 d . . .
H21 H 0.2602 0.3749 0.1902 0.076 Uiso 1 1 calc R . .
C22 C 0.2907(6) 0.5135(5) 0.1769(5) 0.0757(17) Uani 1 1 d . . .
H22 H 0.2077 0.5288 0.1384 0.091 Uiso 1 1 calc R . .
C23 C 0.4992(7) 0.5597(4) 0.2582(5) 0.0772(17) Uani 1 1 d . . .
H23 H 0.5601 0.6069 0.2756 0.093 Uiso 1 1 calc R . .
C24 C 0.3845(6) -0.1753(4) 0.3107(5) 0.0684(14) Uani 1 1 d . . .
H24A H 0.4196 -0.2240 0.3629 0.103 Uiso 1 1 calc R . .
H24B H 0.4070 -0.1868 0.2498 0.103 Uiso 1 1 calc R . .
H24C H 0.2950 -0.1757 0.2892 0.103 Uiso 1 1 calc R . .
C25 C 0.3786(7) 0.5823(4) 0.2012(4) 0.0728(16) Uani 1 1 d . . .
H25 H 0.3565 0.6446 0.1791 0.087 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 O2 1.415(3) . ?
S1 O1 1.446(3) . ?
S1 N3 1.653(3) . ?
S1 C6 1.752(4) . ?
Cl2 C9 1.772(4) . ?
N3 C9 1.408(5) . ?
N3 C5 1.489(5) . ?
C4 C11 1.380(6) . ?
C4 C6 1.384(6) . ?
C5 C8 1.496(6) . ?
C6 C7 1.387(6) . ?
C7 C20 1.385(6) . ?
C8 C14 1.368(7) . ?
C8 C21 1.373(7) . ?
C9 C12 1.316(6) . ?
C10 C20 1.386(6) . ?
C10 C11 1.383(7) . ?
C10 C24 1.507(7) . ?
C12 C13 1.460(6) . ?
C13 C17 1.393(6) . ?
C13 C19 1.403(6) . ?
C14 C23 1.384(8) . ?
C15 C17 1.374(7) . ?
C15 C18 1.389(8) . ?
C16 C19 1.383(8) . ?
C16 C18 1.386(9) . ?
C21 C22 1.368(8) . ?
C22 C25 1.349(10) . ?
C23 C25 1.355(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.1(2) . . ?
O2 S1 N3 106.01(18) . . ?
O1 S1 N3 105.06(18) . . ?
O2 S1 C6 108.59(19) . . ?
O1 S1 C6 107.71(19) . . ?
N3 S1 C6 108.99(17) . . ?
C9 N3 C5 116.0(3) . . ?
C9 N3 S1 119.2(3) . . ?
C5 N3 S1 116.6(3) . . ?
C11 C4 C6 119.5(4) . . ?
N3 C5 C8 109.9(3) . . ?
C4 C6 C7 120.6(4) . . ?
C4 C6 S1 120.9(3) . . ?
C7 C6 S1 118.5(3) . . ?
C6 C7 C20 119.0(4) . . ?
C14 C8 C21 118.3(4) . . ?
C14 C8 C5 120.8(4) . . ?
C21 C8 C5 120.8(4) . . ?
C12 C9 N3 125.8(4) . . ?
C12 C9 Cl2 119.0(3) . . ?
N3 C9 Cl2 114.7(3) . . ?
C20 C10 C11 119.1(4) . . ?
C20 C10 C24 119.7(4) . . ?
C11 C10 C24 121.2(4) . . ?
C4 C11 C10 120.8(4) . . ?
C9 C12 C13 128.2(4) . . ?
C17 C13 C19 117.8(4) . . ?
C17 C13 C12 124.6(4) . . ?
C19 C13 C12 117.5(4) . . ?
C8 C14 C23 120.2(5) . . ?
C17 C15 C18 121.6(5) . . ?
C19 C16 C18 120.2(5) . . ?
C15 C17 C13 120.5(4) . . ?
C16 C18 C15 118.6(5) . . ?
C16 C19 C13 121.2(5) . . ?
C10 C20 C7 121.0(4) . . ?
C22 C21 C8 120.6(5) . . ?
C25 C22 C21 121.0(5) . . ?
C25 C23 C14 120.6(6) . . ?
C22 C25 C23 119.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        71.77
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.083
