# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_EGPH_531
_database_code_depnum_ccdc_archive 'CCDC 1037958'
_audit_update_record             
;
2014-12-06 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;
_audit_creation_date             2014-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_formula_moiety         'C15 H15 Br F N O2 S'
_chemical_formula_sum            'C15 H15 Br F N O2 S'
_chemical_formula_weight         372.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c '
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.571(2)
_cell_length_b                   5.2088(10)
_cell_length_c                   26.139(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.278(2)
_cell_angle_gamma                90
_cell_volume                     1572.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_exptl_absorpt_coefficient_mu    2.759
_exptl_absorpt_correction_T_max  0.516
_exptl_absorpt_correction_T_min  0.337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS Bruker'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5719
_exptl_crystal_description       block
_exptl_crystal_F_000             752.0
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23482
_diffrn_reflns_theta_full        25.9988
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.56
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                2329
_reflns_number_total             3100
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.2911
_refine_diff_density_min         -1.5598
_refine_diff_density_rms         0.1308
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             13.0480
_refine_ls_goodness_of_fit_ref   1.0549
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.0548
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²+2.5502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1504
_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
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br1 Br 0.07471(4) 0.60977(14) 0.38342(2) 0.0823(3) Uani 1.000000 .
S1 S -0.49970(8) 0.46110(19) 0.12001(4) 0.0359(3) Uani 1.000000 .
O1 O -0.4946(3) 0.7204(5) 0.13846(12) 0.0495(7) Uani 1.000000 .
O2 O -0.6066(2) 0.3526(6) 0.10072(12) 0.0510(8) Uani 1.000000 .
C4 C -0.2492(4) 0.4989(9) 0.31378(16) 0.0460(10) Uani 1.000000 .
N1 N -0.4544(3) 0.2805(6) 0.16764(13) 0.0382(7) Uani 1.000000 D
C1 C -0.0515(4) 0.4759(9) 0.34141(16) 0.0471(10) Uani 1.000000 .
C8 C -0.3488(3) 0.3545(8) 0.19771(15) 0.0393(9) Uani 1.000000 .
C9 C -0.3987(3) 0.4333(7) 0.07245(14) 0.0353(8) Uani 1.000000 .
C12 C -0.2366(4) 0.3728(10) -0.00096(17) 0.0545(12) Uani 1.000000 .
F1 F -0.3317(5) -0.0449(6) 0.23616(15) 0.1249(19) Uani 1.000000 .
C5 C -0.2363(4) 0.2971(8) 0.28097(15) 0.0410(9) Uani 1.000000 .
C7 C -0.3397(4) 0.2137(9) 0.24735(16) 0.0528(11) Uani 1.000000 .
C14 C -0.3065(4) 0.5973(9) 0.07158(19) 0.0531(12) Uani 1.000000 .
C10 C -0.4100(4) 0.2368(10) 0.03726(19) 0.0627(14) Uani 1.000000 .
C3 C -0.1571(4) 0.5914(9) 0.34394(17) 0.0500(11) Uani 1.000000 .
C15 C -0.1487(6) 0.3411(15) -0.0409(2) 0.091(2) Uani 1.000000 .
C6 C -0.1290(4) 0.1834(9) 0.2791(2) 0.0583(12) Uani 1.000000 .
C2 C -0.0357(4) 0.2728(10) 0.3100(2) 0.0605(13) Uani 1.000000 .
C11 C -0.3283(5) 0.2082(12) 0.00098(19) 0.0704(15) Uani 1.000000 .
C13 C -0.2256(4) 0.5636(11) 0.0349(2) 0.0638(14) Uani 1.000000 .
H1 H -0.460(3) 0.121(2) 0.1591(14) 0.033(11) Uiso 1.000000 D
H7 H -0.4102(4) 0.2437(9) 0.26557(16) 0.0634(14) Uiso 1.000000 R
H8a H -0.2817(3) 0.3164(8) 0.17839(15) 0.0471(11) Uiso 1.000000 R
H8b H -0.3498(3) 0.5379(8) 0.20418(15) 0.0471(11) Uiso 1.000000 R
H15a H -0.105(3) 0.187(5) -0.0341(11) 0.136(3) Uiso 1.000000 GR
H15b H -0.1877(6) 0.330(10) -0.0742(3) 0.136(3) Uiso 1.000000 GR
H15c H -0.097(3) 0.486(5) -0.0398(13) 0.136(3) Uiso 1.000000 GR
H6 H -0.1189(4) 0.0462(9) 0.2570(2) 0.0699(15) Uiso 1.000000 R
H2 H 0.0364(4) 0.1946(10) 0.3091(2) 0.0726(16) Uiso 1.000000 R
H3 H -0.1665(4) 0.7302(9) 0.36569(17) 0.0600(13) Uiso 1.000000 R
H4 H -0.3215(4) 0.5748(9) 0.31571(16) 0.0552(12) Uiso 1.000000 R
H10 H -0.4721(4) 0.1238(10) 0.03787(19) 0.0752(16) Uiso 1.000000 R
H11 H -0.3359(5) 0.0744(12) -0.02253(19) 0.0845(18) Uiso 1.000000 R
H13 H -0.1623(4) 0.6737(11) 0.0347(2) 0.0765(16) Uiso 1.000000 R
H14 H -0.2981(4) 0.7300(9) 0.09531(19) 0.0637(14) Uiso 1.000000 R


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 C1 1.908(4) . ?
S1 O1 1.434(3) . ?
S1 O2 1.425(3) . ?
S1 N1 1.623(3) . ?
S1 C9 1.760(4) . ?
C4 C5 1.370(6) . ?
C4 C3 1.376(6) . ?
N1 C8 1.467(5) . ?
C1 C3 1.367(6) . ?
C1 C2 1.358(7) . ?
C8 C7 1.489(6) . ?
C9 C14 1.368(6) . ?
C9 C10 1.377(6) . ?
C12 C15 1.507(7) . ?
C12 C11 1.367(7) . ?
C12 C13 1.366(7) . ?
F1 C7 1.383(6) . ?
C5 C7 1.508(6) . ?
C5 C6 1.379(6) . ?
C14 C13 1.390(7) . ?
C10 C11 1.385(7) . ?
C6 C2 1.391(7) . ?

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 120.68(19) . . ?
N1 S1 O1 106.42(18) . . ?
N1 S1 O2 106.09(18) . . ?
C9 S1 O1 107.38(18) . . ?
C9 S1 O2 108.37(18) . . ?
C9 S1 N1 107.21(18) . . ?
C3 C4 C5 121.3(4) . . ?
C8 N1 S1 118.8(3) . . ?
C3 C1 Br1 117.9(4) . . ?
C2 C1 Br1 120.5(3) . . ?
C2 C1 C3 121.6(4) . . ?
C7 C8 N1 110.6(3) . . ?
C14 C9 S1 120.7(3) . . ?
C10 C9 S1 119.4(3) . . ?
C10 C9 C14 119.8(4) . . ?
C11 C12 C15 120.8(5) . . ?
C13 C12 C15 120.9(5) . . ?
C13 C12 C11 118.2(4) . . ?
C7 C5 C4 118.3(4) . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 C7 122.8(4) . . ?
F1 C7 C8 107.3(4) . . ?
C5 C7 C8 112.3(4) . . ?
C5 C7 F1 110.1(4) . . ?
C13 C14 C9 119.3(4) . . ?
C11 C10 C9 119.7(5) . . ?
C1 C3 C4 118.9(4) . . ?
C2 C6 C5 120.4(4) . . ?
C6 C2 C1 119.0(4) . . ?
C10 C11 C12 121.3(5) . . ?
C14 C13 C12 121.7(5) . . ?

_olex2_submission_original_sample_id EGPH-531
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
N1 H1 1 0.8600 0.0010 0.0001

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
