# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_c558
_database_code_depnum_ccdc_archive 'CCDC 903996'
_audit_update_record             
;
2012-10-02 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_jianwang_1349160670.C558.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 Br O2 S'
_chemical_formula_weight         377.29

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.6074(6)
_cell_length_b                   14.7841(16)
_cell_length_c                   20.027(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1660.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4912
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.32

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    2.606
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4126
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11718
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3802
_reflns_number_gt                3550
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0151P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   0.018(7)
_refine_ls_number_reflns         3802
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.27233(10) 0.89710(4) 0.31785(2) 0.01498(12) Uani 1 1 d . . .
Br1 Br 0.78209(5) 0.877843(15) -0.124029(10) 0.02517(8) Uani 1 1 d . . .
O1 O 0.8862(3) 0.79351(11) 0.32159(7) 0.0176(3) Uani 1 1 d . . .
O2 O 0.4033(3) 1.00928(10) 0.17421(7) 0.0164(3) Uani 1 1 d . . .
C1 C 0.7969(4) 0.88901(13) 0.18514(9) 0.0116(4) Uani 1 1 d . . .
H1 H 0.6490 0.8597 0.2027 0.014 Uiso 1 1 calc R . .
C2 C 0.8042(4) 0.98709(14) 0.20988(10) 0.0133(4) Uani 1 1 d . . .
H2A H 0.8195 0.9866 0.2591 0.016 Uiso 1 1 calc R . .
H2B H 0.9487 1.0165 0.1916 0.016 Uiso 1 1 calc R . .
C3 C 0.5902(4) 1.04333(15) 0.19136(10) 0.0119(4) Uani 1 1 d . . .
C4 C 0.6206(4) 1.14420(15) 0.19526(11) 0.0194(5) Uani 1 1 d . . .
H4A H 0.6969 1.1661 0.1543 0.029 Uiso 1 1 calc R . .
H4B H 0.7207 1.1594 0.2338 0.029 Uiso 1 1 calc R . .
H4C H 0.4641 1.1729 0.2003 0.029 Uiso 1 1 calc R . .
C5 C 1.0138(4) 0.83670(16) 0.21146(10) 0.0132(5) Uani 1 1 d . . .
H5A H 1.0083 0.7740 0.1941 0.016 Uiso 1 1 calc R . .
H5B H 1.1611 0.8654 0.1943 0.016 Uiso 1 1 calc R . .
C6 C 1.0244(4) 0.83380(15) 0.28699(10) 0.0124(4) Uani 1 1 d . . .
C7 C 1.2567(4) 0.88132(13) 0.40544(9) 0.0115(4) Uani 1 1 d . . .
C8 C 1.0654(4) 0.91539(15) 0.44229(11) 0.0140(5) Uani 1 1 d . . .
H8 H 0.9351 0.9437 0.4204 0.017 Uiso 1 1 calc R . .
C9 C 1.0680(4) 0.90737(15) 0.51114(11) 0.0155(5) Uani 1 1 d . . .
H9 H 0.9390 0.9308 0.5366 0.019 Uiso 1 1 calc R . .
C10 C 1.2570(4) 0.86553(13) 0.54339(9) 0.0135(4) Uani 1 1 d . . .
H10 H 1.2578 0.8606 0.5907 0.016 Uiso 1 1 calc R . .
C11 C 1.4453(4) 0.83086(15) 0.50614(11) 0.0153(5) Uani 1 1 d . . .
H11 H 1.5740 0.8015 0.5281 0.018 Uiso 1 1 calc R . .
C12 C 1.4461(4) 0.83890(15) 0.43714(10) 0.0125(4) Uani 1 1 d . . .
H12 H 1.5754 0.8155 0.4118 0.015 Uiso 1 1 calc R . .
C13 C 0.7918(4) 0.88483(13) 0.10944(9) 0.0109(4) Uani 1 1 d . . .
C14 C 0.6072(4) 0.84188(15) 0.07537(11) 0.0158(5) Uani 1 1 d . . .
H14 H 0.4820 0.8144 0.1000 0.019 Uiso 1 1 calc R . .
C15 C 0.6024(4) 0.83841(15) 0.00601(11) 0.0175(5) Uani 1 1 d . . .
H15 H 0.4761 0.8087 -0.0168 0.021 Uiso 1 1 calc R . .
C16 C 0.7846(4) 0.87899(14) -0.02890(9) 0.0156(4) Uani 1 1 d . . .
C17 C 0.9716(4) 0.92149(16) 0.00296(11) 0.0160(5) Uani 1 1 d . . .
H17 H 1.0960 0.9488 -0.0221 0.019 Uiso 1 1 calc R . .
C18 C 0.9749(4) 0.92367(15) 0.07192(10) 0.0143(5) Uani 1 1 d . . .
H18 H 1.1042 0.9521 0.0942 0.017 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 C7 1.7717(19) . ?
S1 C6 1.786(2) . ?
Br1 C16 1.9053(19) . ?
O1 C6 1.198(3) . ?
O2 C3 1.212(3) . ?
C1 C13 1.517(3) . ?
C1 C2 1.533(3) . ?
C1 C5 1.535(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.507(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.503(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.514(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C12 1.387(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.393(3) . ?
C13 C18 1.396(3) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C7 S1 C6 103.60(10) . . ?
C13 C1 C2 111.22(16) . . ?
C13 C1 C5 109.73(16) . . ?
C2 C1 C5 110.15(17) . . ?
C13 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
C5 C1 H1 108.6 . . ?
C3 C2 C1 114.92(18) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
O2 C3 C4 121.7(2) . . ?
O2 C3 C2 121.96(19) . . ?
C4 C3 C2 116.39(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C1 112.85(17) . . ?
C6 C5 H5A 109.0 . . ?
C1 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C1 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
O1 C6 C5 124.5(2) . . ?
O1 C6 S1 124.31(16) . . ?
C5 C6 S1 111.18(15) . . ?
C12 C7 C8 120.63(19) . . ?
C12 C7 S1 118.35(16) . . ?
C8 C7 S1 120.92(16) . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 119.66(19) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C14 C13 C18 118.05(19) . . ?
C14 C13 C1 121.47(19) . . ?
C18 C13 C1 120.47(18) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C17 121.90(19) . . ?
C15 C16 Br1 119.91(16) . . ?
C17 C16 Br1 118.19(17) . . ?
C16 C17 C18 118.9(2) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 121.2(2) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?

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
C13 C1 C2 C3 62.5(2) . . . . ?
C5 C1 C2 C3 -175.66(17) . . . . ?
C1 C2 C3 O2 18.3(3) . . . . ?
C1 C2 C3 C4 -161.65(18) . . . . ?
C13 C1 C5 C6 -177.11(18) . . . . ?
C2 C1 C5 C6 60.1(2) . . . . ?
C1 C5 C6 O1 68.1(3) . . . . ?
C1 C5 C6 S1 -112.68(17) . . . . ?
C7 S1 C6 O1 1.3(2) . . . . ?
C7 S1 C6 C5 -177.97(15) . . . . ?
C6 S1 C7 C12 118.31(17) . . . . ?
C6 S1 C7 C8 -65.41(19) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
S1 C7 C8 C9 -175.40(17) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C7 -0.4(3) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
S1 C7 C12 C11 175.92(17) . . . . ?
C2 C1 C13 C14 -121.9(2) . . . . ?
C5 C1 C13 C14 115.9(2) . . . . ?
C2 C1 C13 C18 58.6(3) . . . . ?
C5 C1 C13 C18 -63.5(2) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
C1 C13 C14 C15 179.8(2) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C14 C15 C16 Br1 -178.83(17) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
Br1 C16 C17 C18 179.39(18) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C14 C13 C18 C17 1.4(3) . . . . ?
C1 C13 C18 C17 -179.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.069


