# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mo_160425b
_audit_block_doi                 10.5517/ccdc.csd.cc1lvl56
_database_code_depnum_ccdc_archive 'CCDC 1485308'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Br2 S'
_chemical_formula_weight         424.19

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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

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

_cell_length_a                   7.604(8)
_cell_length_b                   9.541(10)
_cell_length_c                   24.58(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1783(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5794
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      23.43

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   0.3804
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.654
_shelx_estimated_absorpt_T_min   0.251
_shelx_estimated_absorpt_T_max   0.653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21002
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.804
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3893
_reflns_number_gt                2092
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.993

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.8306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 638 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.012(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3893
_refine_ls_number_parameters     190
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.025
_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_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 -0.05743(16) 0.17942(13) 0.84768(4) 0.1096(4) Uani 1 1 d . . . . .
S1 S 0.7041(3) 0.2411(2) 0.69322(13) 0.0884(9) Uani 1 1 d . . . . .
C1 C 0.4869(9) 0.2936(7) 0.6666(3) 0.057(2) Uani 1 1 d . . . . .
H1 H 0.4577 0.2325 0.6358 0.068 Uiso 1 1 calc R U . . .
C2 C 0.3570(10) 0.2677(7) 0.7109(3) 0.0498(19) Uani 1 1 d . . . . .
Br2 Br 0.44937(16) 1.08427(9) 0.50590(4) 0.0929(4) Uani 1 1 d . . . . .
C3 C 0.2930(11) 0.1315(8) 0.7200(3) 0.060(2) Uani 1 1 d . . . . .
H3 H 0.3341 0.0573 0.6991 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1102(9) 0.2161(10) 0.7929(3) 0.062(2) Uani 1 1 d . . . . .
C4 C 0.1686(12) 0.1077(9) 0.7602(4) 0.069(2) Uani 1 1 d . . . . .
H4 H 0.1240 0.0178 0.7652 0.083 Uiso 1 1 calc R U . . .
C6 C 0.1734(11) 0.3476(9) 0.7849(3) 0.065(2) Uani 1 1 d . . . . .
H6 H 0.1342 0.4207 0.8069 0.078 Uiso 1 1 calc R U . . .
C7 C 0.2952(10) 0.3738(8) 0.7447(3) 0.062(2) Uani 1 1 d . . . . .
H7 H 0.3371 0.4645 0.7400 0.074 Uiso 1 1 calc R U . . .
C8 C 0.4924(9) 0.4420(7) 0.6465(3) 0.056(2) Uani 1 1 d . . . . .
H8 H 0.5306 0.5099 0.6710 0.067 Uiso 1 1 calc R U . . .
C9 C 0.4486(11) 0.4850(7) 0.5979(3) 0.0549(18) Uani 1 1 d . . . . .
H9 H 0.4127 0.4161 0.5735 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4493(10) 0.6289(7) 0.5773(3) 0.0457(16) Uani 1 1 d . . . . .
C11 C 0.5144(10) 0.7412(8) 0.6069(3) 0.058(2) Uani 1 1 d . . . . .
H11 H 0.5602 0.7254 0.6414 0.070 Uiso 1 1 calc R U . . .
C12 C 0.5131(11) 0.8759(7) 0.5864(3) 0.062(2) Uani 1 1 d . . . . .
H12 H 0.5588 0.9493 0.6069 0.074 Uiso 1 1 calc R U . . .
C13 C 0.4452(11) 0.9007(7) 0.5365(3) 0.0585(19) Uani 1 1 d . . . . .
C14 C 0.3786(11) 0.7941(9) 0.5058(3) 0.074(2) Uani 1 1 d . . . . .
H14 H 0.3334 0.8118 0.4714 0.089 Uiso 1 1 calc R U . . .
C15 C 0.3791(10) 0.6585(9) 0.5266(3) 0.065(2) Uani 1 1 d . . . . .
H15 H 0.3313 0.5861 0.5061 0.078 Uiso 1 1 calc R U . . .
C16 C 0.8538(16) 0.2779(12) 0.6378(5) 0.116(4) Uani 1 1 d . U . . .
H16A H 0.8066 0.3561 0.6173 0.139 Uiso 1 1 calc R U . . .
H16B H 0.9647 0.3083 0.6534 0.139 Uiso 1 1 calc R U . . .
C17 C 0.8872(18) 0.1732(15) 0.6030(5) 0.115(4) Uani 1 1 d . U . . .
H17 H 0.7906 0.1497 0.5816 0.138 Uiso 1 1 calc R U . . .
C18 C 1.0241(18) 0.0978(13) 0.5926(5) 0.125(4) Uani 1 1 d . U . . .
H18A H 1.1280 0.1127 0.6117 0.150 Uiso 1 1 calc R U . . .
H18B H 1.0189 0.0286 0.5660 0.150 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 C5 1.887(8) . ?
S1 C16 1.809(11) . ?
S1 C1 1.846(8) . ?
C1 C2 1.491(10) . ?
C1 C8 1.500(9) . ?
C1 H1 0.9800 . ?
C2 C7 1.391(10) . ?
C2 C3 1.406(10) . ?
Br2 C13 1.907(7) . ?
C3 C4 1.386(11) . ?
C3 H3 0.9300 . ?
C5 C6 1.358(12) . ?
C5 C4 1.383(11) . ?
C4 H4 0.9300 . ?
C6 C7 1.379(10) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.308(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.463(9) . ?
C9 H9 0.9300 . ?
C10 C15 1.384(10) . ?
C10 C11 1.386(9) . ?
C11 C12 1.380(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.351(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(11) . ?
C14 C15 1.391(12) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.341(16) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.291(15) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9300 . ?
C18 H18B 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
C16 S1 C1 104.1(5) . . ?
C2 C1 C8 114.5(6) . . ?
C2 C1 S1 106.8(5) . . ?
C8 C1 S1 110.4(5) . . ?
C2 C1 H1 108.3 . . ?
C8 C1 H1 108.3 . . ?
S1 C1 H1 108.3 . . ?
C7 C2 C3 117.4(7) . . ?
C7 C2 C1 122.6(6) . . ?
C3 C2 C1 120.0(6) . . ?
C4 C3 C2 120.1(7) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C6 C5 C4 119.6(7) . . ?
C6 C5 Br1 120.9(7) . . ?
C4 C5 Br1 119.5(6) . . ?
C5 C4 C3 120.7(7) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C5 C6 C7 120.6(8) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 121.6(7) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C9 C8 C1 126.1(7) . . ?
C9 C8 H8 116.9 . . ?
C1 C8 H8 116.9 . . ?
C8 C9 C10 127.5(7) . . ?
C8 C9 H9 116.2 . . ?
C10 C9 H9 116.2 . . ?
C15 C10 C11 116.9(6) . . ?
C15 C10 C9 120.0(7) . . ?
C11 C10 C9 123.1(6) . . ?
C12 C11 C10 121.8(6) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C13 C12 C11 119.8(7) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.9(6) . . ?
C12 C13 Br2 120.9(6) . . ?
C14 C13 Br2 118.2(6) . . ?
C13 C14 C15 119.3(7) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C14 121.4(7) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 S1 117.1(8) . . ?
C17 C16 H16A 108.0 . . ?
S1 C16 H16A 108.0 . . ?
C17 C16 H16B 108.0 . . ?
S1 C16 H16B 108.0 . . ?
H16A C16 H16B 107.3 . . ?
C18 C17 C16 134.0(14) . . ?
C18 C17 H17 113.0 . . ?
C16 C17 H17 113.0 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?

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
C16 S1 C1 C2 -179.2(6) . . . . ?
C16 S1 C1 C8 -54.1(7) . . . . ?
C8 C1 C2 C7 -23.0(10) . . . . ?
S1 C1 C2 C7 99.4(7) . . . . ?
C8 C1 C2 C3 157.4(7) . . . . ?
S1 C1 C2 C3 -80.2(8) . . . . ?
C7 C2 C3 C4 2.1(11) . . . . ?
C1 C2 C3 C4 -178.2(7) . . . . ?
C6 C5 C4 C3 1.0(12) . . . . ?
Br1 C5 C4 C3 -179.3(6) . . . . ?
C2 C3 C4 C5 -2.1(12) . . . . ?
C4 C5 C6 C7 -0.1(12) . . . . ?
Br1 C5 C6 C7 -179.7(6) . . . . ?
C5 C6 C7 C2 0.2(12) . . . . ?
C3 C2 C7 C6 -1.2(11) . . . . ?
C1 C2 C7 C6 179.2(7) . . . . ?
C2 C1 C8 C9 -114.7(9) . . . . ?
S1 C1 C8 C9 124.8(8) . . . . ?
C1 C8 C9 C10 178.8(7) . . . . ?
C8 C9 C10 C15 -172.3(8) . . . . ?
C8 C9 C10 C11 6.1(13) . . . . ?
C15 C10 C11 C12 -1.4(11) . . . . ?
C9 C10 C11 C12 -179.9(8) . . . . ?
C10 C11 C12 C13 0.7(12) . . . . ?
C11 C12 C13 C14 -0.4(13) . . . . ?
C11 C12 C13 Br2 -177.6(6) . . . . ?
C12 C13 C14 C15 0.8(13) . . . . ?
Br2 C13 C14 C15 178.0(6) . . . . ?
C11 C10 C15 C14 1.8(12) . . . . ?
C9 C10 C15 C14 -179.7(8) . . . . ?
C13 C14 C15 C10 -1.5(13) . . . . ?
C1 S1 C16 C17 -92.3(11) . . . . ?
S1 C16 C17 C18 -111.2(14) . . . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.079

