# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cyclohexyl_dimer
_database_code_depnum_ccdc_archive 'CCDC 1885228'
loop_
_audit_author_name
_audit_author_address
'Jeffery Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2018-12-14 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H42 S4'
_chemical_formula_sum            'C34 H42 S4'
_chemical_formula_weight         578.91

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.3616(17)
_cell_length_b                   9.0556(7)
_cell_length_c                   15.3872(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.439(3)
_cell_angle_gamma                90
_cell_volume                     2967.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9428
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.11
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.177
_exptl_absorpt_coefficient_mu    0.343
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.635101
_exptl_absorpt_correction_T_max  0.745490
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6620
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         27.174
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6620
_reflns_number_gt                6254
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, TWINABS V2012/1 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_refine_special_details          
;Refined as a 2-component twin.

Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution.,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)+(0.0968P)²+4.3896P] 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_number_reflns         6620
_refine_ls_number_parameters     246
_refine_ls_number_restraints     265
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1595
_refine_ls_wR_factor_gt          0.1568
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.101
_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
S2 S 0.65468(3) 0.29367(7) 0.49975(4) 0.0243(2) Uani 1 1 d . . . . .
C1 C 0.52658(11) 0.5821(3) 0.74034(15) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.59068(10) 0.5738(3) 0.71881(14) 0.0163(4) Uani 1 1 d . . . . .
C3 C 0.63068(11) 0.6974(3) 0.72920(14) 0.0175(5) Uani 1 1 d . . . . .
C4 C 0.69336(11) 0.6795(3) 0.71180(15) 0.0204(5) Uani 1 1 d . . . . .
H4 H 0.721924 0.758883 0.723013 0.024 Uiso 1 1 calc R U . . .
C5 C 0.71489(11) 0.5478(3) 0.67837(15) 0.0200(5) Uani 1 1 d . . . . .
H5 H 0.757819 0.538352 0.667157 0.024 Uiso 1 1 calc R U . . .
C6 C 0.67423(11) 0.4303(3) 0.66127(15) 0.0186(5) Uani 1 1 d . . . . .
C7 C 0.61282(11) 0.4421(3) 0.68543(15) 0.0196(5) Uani 1 1 d . . . . .
H7 H 0.585633 0.359084 0.679054 0.024 Uiso 1 1 calc R U . . .
C8 C 0.60652(13) 0.8464(3) 0.75311(16) 0.0256(5) Uani 1 1 d D . . . .
H8A H 0.642502 0.910888 0.771755 0.031 Uiso 1 1 calc R U . A 1
H8B H 0.580301 0.835600 0.803038 0.031 Uiso 1 1 calc R U . A 1
C9 C 0.69397(13) 0.2994(3) 0.60965(17) 0.0250(5) Uani 1 1 d . . . . .
H9A H 0.684286 0.207619 0.640905 0.030 Uiso 1 1 calc R U . . .
H9B H 0.739953 0.303158 0.605443 0.030 Uiso 1 1 calc R U . . .
S1 S 0.55973(11) 0.9349(3) 0.66203(17) 0.0268(4) Uani 0.762(6) 1 d D U P B 1
C10 C 0.6075(3) 0.9195(9) 0.5696(4) 0.0283(15) Uani 0.762(6) 1 d D U P B 1
H10A H 0.627413 1.016424 0.560321 0.034 Uiso 0.762(6) 1 calc R U P B 1
H10B H 0.641598 0.847568 0.584388 0.034 Uiso 0.762(6) 1 calc R U P B 1
C11 C 0.5720(2) 0.8713(6) 0.4836(3) 0.0215(10) Uani 0.762(6) 1 d D U P B 1
H11 H 0.540444 0.949776 0.466576 0.026 Uiso 0.762(6) 1 calc R U P B 1
C12 C 0.5364(3) 0.7254(6) 0.4899(7) 0.0264(12) Uani 0.762(6) 1 d D U P B 1
H12A H 0.493959 0.736350 0.459858 0.032 Uiso 0.762(6) 1 calc R U P B 1
H12B H 0.531252 0.703739 0.552033 0.032 Uiso 0.762(6) 1 calc R U P B 1
C13 C 0.56975(16) 0.5946(4) 0.4497(3) 0.0244(8) Uani 0.762(6) 1 d D U P B 1
H13A H 0.553626 0.500864 0.472381 0.029 Uiso 0.762(6) 1 calc R U P B 1
H13B H 0.560687 0.595434 0.385638 0.029 Uiso 0.762(6) 1 calc R U P B 1
C14 C 0.64079(16) 0.6038(4) 0.4718(3) 0.0216(7) Uani 0.762(6) 1 d D U P B 1
H14 H 0.647059 0.620952 0.536041 0.026 Uiso 0.762(6) 1 calc R U P B 1
C15 C 0.6673(2) 0.7405(5) 0.4280(3) 0.0176(9) Uani 0.762(6) 1 d D U P B 1
H15A H 0.703526 0.778491 0.465402 0.021 Uiso 0.762(6) 1 calc R U P B 1
H15B H 0.682741 0.710711 0.371618 0.021 Uiso 0.762(6) 1 calc R U P B 1
C16 C 0.61902(16) 0.8648(4) 0.4120(2) 0.0191(7) Uani 0.762(6) 1 d D U P B 1
H16A H 0.595581 0.849536 0.354606 0.023 Uiso 0.762(6) 1 calc R U P B 1
H16B H 0.641326 0.960468 0.410019 0.023 Uiso 0.762(6) 1 calc R U P B 1
S1B S 0.5747(5) 0.9575(11) 0.6634(6) 0.042(2) Uani 0.238(6) 1 d D U P B 2
C10B C 0.6201(9) 0.910(3) 0.5787(11) 0.020(3) Uani 0.238(6) 1 d D U P B 2
H10C H 0.650250 0.991108 0.570501 0.024 Uiso 0.238(6) 1 calc R U P B 2
H10D H 0.644686 0.820715 0.595670 0.024 Uiso 0.238(6) 1 calc R U P B 2
C11B C 0.5823(8) 0.8805(19) 0.4909(12) 0.028(3) Uani 0.238(6) 1 d D U P B 2
H11B H 0.558151 0.968784 0.468099 0.033 Uiso 0.238(6) 1 calc R U P B 2
C12B C 0.5430(8) 0.7406(16) 0.488(2) 0.027(3) Uani 0.238(6) 1 d D U P B 2
H12C H 0.518362 0.734978 0.430916 0.032 Uiso 0.238(6) 1 calc R U P B 2
H12D H 0.512952 0.746275 0.533770 0.032 Uiso 0.238(6) 1 calc R U P B 2
C13B C 0.5822(5) 0.5993(10) 0.5015(7) 0.019(2) Uani 0.238(6) 1 d D U P B 2
H13C H 0.553796 0.512976 0.502513 0.023 Uiso 0.238(6) 1 calc R U P B 2
H13D H 0.607127 0.604204 0.558368 0.023 Uiso 0.238(6) 1 calc R U P B 2
C14B C 0.6267(5) 0.5797(10) 0.4279(7) 0.019(2) Uani 0.238(6) 1 d D U P B 2
H14B H 0.601872 0.545266 0.373900 0.022 Uiso 0.238(6) 1 calc R U P B 2
C15B C 0.6609(9) 0.7205(14) 0.4080(13) 0.029(3) Uani 0.238(6) 1 d D U P B 2
H15C H 0.706233 0.703117 0.423087 0.035 Uiso 0.238(6) 1 calc R U P B 2
H15D H 0.655619 0.735649 0.344096 0.035 Uiso 0.238(6) 1 calc R U P B 2
C16B C 0.6444(8) 0.8608(15) 0.4494(12) 0.048(3) Uani 0.238(6) 1 d D U P B 2
H16C H 0.646355 0.938996 0.404764 0.058 Uiso 0.238(6) 1 calc R U P B 2
H16D H 0.678307 0.882245 0.495299 0.058 Uiso 0.238(6) 1 calc R U P B 2
C17 C 0.67865(12) 0.4671(3) 0.45299(17) 0.0240(5) Uani 1 1 d D . . . .
H17A H 0.722923 0.485655 0.474044 0.029 Uiso 0.762(6) 1 calc R U P B 1
H17B H 0.677414 0.454599 0.388966 0.029 Uiso 0.762(6) 1 calc R U P B 1
H17C H 0.709620 0.514631 0.495300 0.029 Uiso 0.238(6) 1 calc R U P B 2
H17D H 0.700514 0.444267 0.400173 0.029 Uiso 0.238(6) 1 calc R U P B 2


_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.
;

_exptl_special_details           
; 
All crystals examined exhibited non-merohedral twinning.  Two distinct 
cells were identified using APEX3 (Bruker, 2016) and Cell_Now 
(Sheldrick, 2008).  Ten frame series were integrated and filtered for 
statistical outliers using SAINT (Bruker, 2016) then corrected for 
absorption by integration using SAINT/TWINABS v2014/2 (Bruker, 2016) to 
sort, merge, and scale the combined data.  Combined unit cell parameters 
were determined from both components using SAINT (Bruker, 2013).  The 
twin law by rows was (1 0 0.216), (0 -1 0), (0 0 -1).  Non-overlapping 
reflections from the primary orientation were used for phasing.  Combined 
data with complete or no overlap were used for refinement. No decay 
correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0860
0.00 1.00 0.00 0.0160
-1.00 0.00 0.00 0.1810
0.00 0.00 1.00 0.1740
1.00 0.00 -2.00 0.0380
2.00 3.00 -4.00 0.0250

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
S2 C17 1.817(3) . ?
S2 C9 1.830(3) . ?
C1 C1 1.196(5) 2_656 ?
C1 C2 1.435(3) . ?
C2 C7 1.396(3) . ?
C2 C3 1.410(3) . ?
C3 C4 1.395(3) . ?
C3 C8 1.501(3) . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 C9 1.505(3) . ?
C7 H7 0.9500 . ?
C8 S1B 1.798(9) . ?
C8 S1 1.841(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
S1 C10 1.820(5) . ?
C10 C11 1.537(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.531(6) . ?
C11 C16 1.549(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.537(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.531(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C17 1.519(4) . ?
C14 C15 1.537(5) . ?
C14 H14 1.0000 . ?
C15 C16 1.534(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
S1B C10B 1.737(11) . ?
C10B C11B 1.543(12) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.518(12) . ?
C11B C16B 1.527(12) . ?
C11B H11B 1.0000 . ?
C12B C13B 1.534(13) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.545(10) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.513(11) . ?
C14B C17 1.535(9) . ?
C14B H14B 1.0000 . ?
C15B C16B 1.477(12) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 H17C 0.9900 . ?
C17 H17D 0.9900 . ?

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
C17 S2 C9 102.61(12) . . ?
C1 C1 C2 176.83(17) 2_656 . ?
C7 C2 C3 120.0(2) . . ?
C7 C2 C1 119.1(2) . . ?
C3 C2 C1 120.9(2) . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 C8 120.3(2) . . ?
C2 C3 C8 121.7(2) . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 118.6(2) . . ?
C5 C6 C9 120.5(2) . . ?
C7 C6 C9 120.5(2) . . ?
C6 C7 C2 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C3 C8 S1B 115.6(4) . . ?
C3 C8 S1 112.44(19) . . ?
C3 C8 H8A 109.1 . . ?
S1 C8 H8A 109.1 . . ?
C3 C8 H8B 109.1 . . ?
S1 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C6 C9 S2 112.51(17) . . ?
C6 C9 H9A 109.1 . . ?
S2 C9 H9A 109.1 . . ?
C6 C9 H9B 109.1 . . ?
S2 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C10 S1 C8 104.9(3) . . ?
C11 C10 S1 115.1(4) . . ?
C11 C10 H10A 108.5 . . ?
S1 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
S1 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 113.9(5) . . ?
C12 C11 C16 111.4(4) . . ?
C10 C11 C16 108.6(4) . . ?
C12 C11 H11 107.6 . . ?
C10 C11 H11 107.6 . . ?
C16 C11 H11 107.6 . . ?
C11 C12 C13 113.0(4) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 110.6(3) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C17 C14 C13 116.6(3) . . ?
C17 C14 C15 110.7(3) . . ?
C13 C14 C15 109.8(3) . . ?
C17 C14 H14 106.4 . . ?
C13 C14 H14 106.4 . . ?
C15 C14 H14 106.4 . . ?
C16 C15 C14 113.4(3) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C11 112.2(3) . . ?
C15 C16 H16A 109.2 . . ?
C11 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C11 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C10B S1B C8 103.8(10) . . ?
C11B C10B S1B 114.6(12) . . ?
C11B C10B H10C 108.6 . . ?
S1B C10B H10C 108.6 . . ?
C11B C10B H10D 108.6 . . ?
S1B C10B H10D 108.6 . . ?
H10C C10B H10D 107.6 . . ?
C12B C11B C16B 112.8(11) . . ?
C12B C11B C10B 114.9(15) . . ?
C16B C11B C10B 88.5(11) . . ?
C12B C11B H11B 112.8 . . ?
C16B C11B H11B 112.8 . . ?
C10B C11B H11B 112.8 . . ?
C11B C12B C13B 113.4(12) . . ?
C11B C12B H12C 108.9 . . ?
C13B C12B H12C 108.9 . . ?
C11B C12B H12D 108.9 . . ?
C13B C12B H12D 108.9 . . ?
H12C C12B H12D 107.7 . . ?
C12B C13B C14B 110.9(12) . . ?
C12B C13B H13C 109.5 . . ?
C14B C13B H13C 109.5 . . ?
C12B C13B H13D 109.5 . . ?
C14B C13B H13D 109.5 . . ?
H13C C13B H13D 108.0 . . ?
C15B C14B C17 105.0(10) . . ?
C15B C14B C13B 112.7(8) . . ?
C17 C14B C13B 111.5(8) . . ?
C15B C14B H14B 109.2 . . ?
C17 C14B H14B 109.2 . . ?
C13B C14B H14B 109.2 . . ?
C16B C15B C14B 120.1(10) . . ?
C16B C15B H15C 107.3 . . ?
C14B C15B H15C 107.3 . . ?
C16B C15B H15D 107.3 . . ?
C14B C15B H15D 107.3 . . ?
H15C C15B H15D 106.9 . . ?
C15B C16B C11B 121.7(11) . . ?
C15B C16B H16C 106.9 . . ?
C11B C16B H16C 106.9 . . ?
C15B C16B H16D 106.9 . . ?
C11B C16B H16D 106.9 . . ?
H16C C16B H16D 106.7 . . ?
C14 C17 S2 117.29(19) . . ?
C14B C17 S2 117.0(4) . . ?
C14 C17 H17A 108.0 . . ?
S2 C17 H17A 108.0 . . ?
C14 C17 H17B 108.0 . . ?
S2 C17 H17B 108.0 . . ?
H17A C17 H17B 107.2 . . ?
C14B C17 H17C 108.1 . . ?
S2 C17 H17C 108.1 . . ?
C14B C17 H17D 108.1 . . ?
S2 C17 H17D 108.1 . . ?
H17C C17 H17D 107.3 . . ?

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
C7 C2 C3 C4 -5.0(3) . . . . ?
C1 C2 C3 C4 176.4(2) . . . . ?
C7 C2 C3 C8 171.5(2) . . . . ?
C1 C2 C3 C8 -7.1(3) . . . . ?
C2 C3 C4 C5 5.2(3) . . . . ?
C8 C3 C4 C5 -171.3(2) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 -5.6(3) . . . . ?
C4 C5 C6 C9 168.2(2) . . . . ?
C5 C6 C7 C2 5.8(3) . . . . ?
C9 C6 C7 C2 -168.1(2) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
C1 C2 C7 C6 178.1(2) . . . . ?
C4 C3 C8 S1B 90.8(4) . . . . ?
C2 C3 C8 S1B -85.6(4) . . . . ?
C4 C3 C8 S1 103.4(2) . . . . ?
C2 C3 C8 S1 -73.0(3) . . . . ?
C5 C6 C9 S2 -107.5(2) . . . . ?
C7 C6 C9 S2 66.3(3) . . . . ?
C17 S2 C9 C6 59.6(2) . . . . ?
C3 C8 S1 C10 -49.2(3) . . . . ?
C8 S1 C10 C11 135.6(5) . . . . ?
S1 C10 C11 C12 -55.6(6) . . . . ?
S1 C10 C11 C16 179.6(4) . . . . ?
C10 C11 C12 C13 -103.3(7) . . . . ?
C16 C11 C12 C13 20.0(7) . . . . ?
C11 C12 C13 C14 40.1(7) . . . . ?
C12 C13 C14 C17 167.6(4) . . . . ?
C12 C13 C14 C15 -65.5(5) . . . . ?
C17 C14 C15 C16 156.7(3) . . . . ?
C13 C14 C15 C16 26.6(4) . . . . ?
C14 C15 C16 C11 33.2(5) . . . . ?
C12 C11 C16 C15 -58.5(5) . . . . ?
C10 C11 C16 C15 67.8(5) . . . . ?
C3 C8 S1B C10B -33.4(9) . . . . ?
C8 S1B C10B C11B 134.2(15) . . . . ?
S1B C10B C11B C12B -70(2) . . . . ?
S1B C10B C11B C16B 175.9(17) . . . . ?
C16B C11B C12B C13B 37(2) . . . . ?
C10B C11B C12B C13B -63(2) . . . . ?
C11B C12B C13B C14B -63(2) . . . . ?
C12B C13B C14B C15B 45.8(17) . . . . ?
C12B C13B C14B C17 163.6(12) . . . . ?
C17 C14B C15B C16B -128.9(19) . . . . ?
C13B C14B C15B C16B -7(2) . . . . ?
C14B C15B C16B C11B -18(3) . . . . ?
C12B C11B C16B C15B 3(3) . . . . ?
C10B C11B C16B C15B 119(2) . . . . ?
C13 C14 C17 S2 -53.9(4) . . . . ?
C15 C14 C17 S2 179.7(2) . . . . ?
C15B C14B C17 S2 169.4(8) . . . . ?
C13B C14B C17 S2 47.0(9) . . . . ?
C9 S2 C17 C14 -84.3(3) . . . . ?
C9 S2 C17 C14B -116.4(5) . . . . ?

_refine_diff_density_max         0.797
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_adamantyl
_database_code_depnum_ccdc_archive 'CCDC 1885229'
loop_
_audit_author_name
_audit_author_address
'Jeffery Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2018-12-14 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 Br2 S2'
_chemical_formula_sum            'C20 H24 Br2 S2'
_chemical_formula_weight         488.33

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   10.1337(10)
_cell_length_b                   12.5991(13)
_cell_length_c                   30.300(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3868.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.31
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    4.407
_shelx_estimated_absorpt_T_min   0.375
_shelx_estimated_absorpt_T_max   0.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.49984
_exptl_absorpt_correction_T_max  0.67886
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_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  'multilayer mirrors'
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29762
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.418
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4834
_reflns_number_gt                4310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v817 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0163P)²+2.9343P] 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_number_reflns         4834
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0446
_refine_ls_wR_factor_gt          0.0433
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.004
_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 0.56511(2) 0.42938(2) 0.70240(2) 0.01808(4) Uani 1 1 d . . . . .
Br2 Br 0.90529(2) 0.71323(2) 0.56225(2) 0.01472(4) Uani 1 1 d . . . . .
S1 S 0.56582(4) 0.71030(4) 0.73242(2) 0.01825(9) Uani 1 1 d . . . . .
S2 S 0.58004(4) 0.65501(3) 0.51949(2) 0.01343(8) Uani 1 1 d . . . . .
C1 C 0.66356(15) 0.51470(12) 0.66257(5) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.73640(15) 0.60127(13) 0.67777(5) 0.0132(3) Uani 1 1 d . . . . .
C3 C 0.81276(15) 0.65516(12) 0.64659(5) 0.0130(3) Uani 1 1 d . . . . .
H3 H 0.872282 0.708814 0.656020 0.016 Uiso 1 1 calc R U . . .
C4 C 0.80273(15) 0.63135(12) 0.60222(5) 0.0116(3) Uani 1 1 d . . . . .
C5 C 0.71621(15) 0.55382(11) 0.58644(5) 0.0111(3) Uani 1 1 d . . . . .
C6 C 0.65248(15) 0.49162(12) 0.61801(5) 0.0124(3) Uani 1 1 d . . . . .
H6 H 0.600836 0.432676 0.608846 0.015 Uiso 1 1 calc R U . . .
C7 C 0.72512(16) 0.64521(14) 0.72358(5) 0.0177(3) Uani 1 1 d . . . . .
H7A H 0.796971 0.697054 0.728624 0.021 Uiso 1 1 calc R U . . .
H7B H 0.735636 0.586908 0.745202 0.021 Uiso 1 1 calc R U . . .
C8 C 0.67947(15) 0.54249(12) 0.53876(5) 0.0127(3) Uani 1 1 d . . . . .
H8A H 0.628956 0.475964 0.534653 0.015 Uiso 1 1 calc R U . . .
H8B H 0.760780 0.537571 0.520763 0.015 Uiso 1 1 calc R U . . .
C9 C 0.56664(16) 0.82201(13) 0.69376(5) 0.0166(3) Uani 1 1 d . . . . .
H9A H 0.554309 0.888310 0.710801 0.020 Uiso 1 1 calc R U . . .
H9B H 0.654747 0.825616 0.679722 0.020 Uiso 1 1 calc R U . . .
C10 C 0.46199(15) 0.81848(12) 0.65716(5) 0.0127(3) Uani 1 1 d . . . . .
C11 C 0.32323(15) 0.79568(12) 0.67532(5) 0.0138(3) Uani 1 1 d . . . . .
H11A H 0.322852 0.726132 0.690522 0.017 Uiso 1 1 calc R U . . .
H11B H 0.298828 0.850912 0.697075 0.017 Uiso 1 1 calc R U . . .
C12 C 0.22244(15) 0.79454(12) 0.63774(5) 0.0139(3) Uani 1 1 d . . . . .
H12 H 0.132810 0.778989 0.649944 0.017 Uiso 1 1 calc R U . . .
C13 C 0.22079(16) 0.90289(12) 0.61462(6) 0.0177(3) Uani 1 1 d . . . . .
H13A H 0.155465 0.902236 0.590324 0.021 Uiso 1 1 calc R U . . .
H13B H 0.195055 0.958854 0.635876 0.021 Uiso 1 1 calc R U . . .
C14 C 0.35856(16) 0.92641(12) 0.59617(6) 0.0169(3) Uani 1 1 d . . . . .
H14 H 0.358058 0.997302 0.581326 0.020 Uiso 1 1 calc R U . . .
C15 C 0.45944(16) 0.92723(12) 0.63378(6) 0.0165(3) Uani 1 1 d . . . . .
H15A H 0.436087 0.983299 0.655298 0.020 Uiso 1 1 calc R U . . .
H15B H 0.548125 0.943386 0.621834 0.020 Uiso 1 1 calc R U . . .
C16 C 0.49685(15) 0.73355(11) 0.62273(5) 0.0108(3) Uani 1 1 d . . . . .
H16A H 0.585947 0.748115 0.610774 0.013 Uiso 1 1 calc R U . . .
H16B H 0.499042 0.663106 0.637183 0.013 Uiso 1 1 calc R U . . .
C17 C 0.39758(15) 0.73105(11) 0.58479(5) 0.0111(3) Uani 1 1 d . . . . .
C18 C 0.39539(16) 0.84027(12) 0.56238(5) 0.0153(3) Uani 1 1 d . . . . .
H18A H 0.330254 0.840018 0.538033 0.018 Uiso 1 1 calc R U . . .
H18B H 0.483329 0.855864 0.549714 0.018 Uiso 1 1 calc R U . . .
C19 C 0.26009(15) 0.70869(12) 0.60418(5) 0.0137(3) Uani 1 1 d . . . . .
H19A H 0.194043 0.707096 0.580117 0.016 Uiso 1 1 calc R U . . .
H19B H 0.260059 0.638398 0.618784 0.016 Uiso 1 1 calc R U . . .
C20 C 0.42780(15) 0.64223(12) 0.55140(5) 0.0137(3) Uani 1 1 d . . . . .
H20A H 0.353107 0.637854 0.530422 0.016 Uiso 1 1 calc R U . . .
H20B H 0.431148 0.574098 0.567646 0.016 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Two frame 
series were integrated and filtered for statistical outliers using SAINT 
(Bruker, 2016) then corrected for absorption by integration using 
SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale the combined 
data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 1.00 0.0490
0.00 -1.00 2.00 0.1110
1.00 -2.00 1.00 0.0910
-1.00 2.00 -1.00 0.0670
1.00 1.00 -2.00 0.0970
-2.00 2.00 1.00 0.0460
0.00 -2.00 1.00 0.0890
0.00 -1.00 -2.00 0.0660
0.00 0.00 -1.00 0.0750
-1.00 -2.00 -2.00 0.0810
1.00 2.00 2.00 0.0630
-1.00 0.00 2.00 0.0720

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 1.8993(15) . ?
Br2 C4 1.9003(15) . ?
S1 C7 1.8304(17) . ?
S1 C9 1.8313(17) . ?
S2 C20 1.8279(16) . ?
S2 C8 1.8347(15) . ?
C1 C6 1.386(2) . ?
C1 C2 1.395(2) . ?
C2 C3 1.397(2) . ?
C2 C7 1.499(2) . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(2) . ?
C5 C6 1.395(2) . ?
C5 C8 1.499(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.535(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C16 1.536(2) . ?
C10 C11 1.537(2) . ?
C10 C15 1.543(2) . ?
C11 C12 1.530(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C19 1.533(2) . ?
C12 C13 1.535(2) . ?
C12 H12 1.0000 . ?
C13 C14 1.533(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.531(2) . ?
C14 C18 1.538(2) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.528(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.535(2) . ?
C17 C19 1.538(2) . ?
C17 C20 1.539(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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 C9 104.28(8) . . ?
C20 S2 C8 103.13(7) . . ?
C6 C1 C2 121.92(14) . . ?
C6 C1 Br1 117.24(12) . . ?
C2 C1 Br1 120.70(12) . . ?
C1 C2 C3 116.71(14) . . ?
C1 C2 C7 123.66(14) . . ?
C3 C2 C7 119.28(14) . . ?
C4 C3 C2 120.79(14) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 122.08(14) . . ?
C3 C4 Br2 117.53(12) . . ?
C5 C4 Br2 120.32(11) . . ?
C6 C5 C4 116.66(14) . . ?
C6 C5 C8 119.50(13) . . ?
C4 C5 C8 123.53(14) . . ?
C1 C6 C5 120.84(14) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C2 C7 S1 111.61(11) . . ?
C2 C7 H7A 109.3 . . ?
S1 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
S1 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C5 C8 S2 111.69(10) . . ?
C5 C8 H8A 109.3 . . ?
S2 C8 H8A 109.3 . . ?
C5 C8 H8B 109.3 . . ?
S2 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 S1 115.89(11) . . ?
C10 C9 H9A 108.3 . . ?
S1 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
S1 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 C16 110.62(13) . . ?
C9 C10 C11 112.27(13) . . ?
C16 C10 C11 108.87(12) . . ?
C9 C10 C15 108.51(13) . . ?
C16 C10 C15 108.10(12) . . ?
C11 C10 C15 108.36(13) . . ?
C12 C11 C10 110.26(13) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C19 109.52(12) . . ?
C11 C12 C13 109.80(13) . . ?
C19 C12 C13 109.12(13) . . ?
C11 C12 H12 109.5 . . ?
C19 C12 H12 109.5 . . ?
C13 C12 H12 109.5 . . ?
C14 C13 C12 109.18(13) . . ?
C14 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C15 C14 C13 109.76(13) . . ?
C15 C14 C18 109.76(13) . . ?
C13 C14 C18 109.11(13) . . ?
C15 C14 H14 109.4 . . ?
C13 C14 H14 109.4 . . ?
C18 C14 H14 109.4 . . ?
C14 C15 C10 110.30(13) . . ?
C14 C15 H15A 109.6 . . ?
C10 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C10 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C10 111.97(12) . . ?
C17 C16 H16A 109.2 . . ?
C10 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C10 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 108.90(12) . . ?
C16 C17 C19 108.23(12) . . ?
C18 C17 C19 108.67(12) . . ?
C16 C17 C20 112.24(12) . . ?
C18 C17 C20 111.34(13) . . ?
C19 C17 C20 107.35(12) . . ?
C17 C18 C14 109.98(13) . . ?
C17 C18 H18A 109.7 . . ?
C14 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
C14 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C12 C19 C17 110.47(12) . . ?
C12 C19 H19A 109.6 . . ?
C17 C19 H19A 109.6 . . ?
C12 C19 H19B 109.6 . . ?
C17 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C17 C20 S2 116.84(11) . . ?
C17 C20 H20A 108.1 . . ?
S2 C20 H20A 108.1 . . ?
C17 C20 H20B 108.1 . . ?
S2 C20 H20B 108.1 . . ?
H20A C20 H20B 107.3 . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_cyclohexyl
_database_code_depnum_ccdc_archive 'CCDC 1885230'
loop_
_audit_author_name
_audit_author_address
'Jeffery Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2018-12-14 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Br2 S2'
_chemical_formula_sum            'C16 H20 Br2 S2'
_chemical_formula_weight         436.26

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   12.5420(6)
_cell_length_b                   9.1015(5)
_cell_length_c                   28.8047(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3288.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9241
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.29
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.149
_exptl_absorpt_coefficient_mu    5.173
_shelx_estimated_absorpt_T_min   0.367
_shelx_estimated_absorpt_T_max   0.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3843
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            168917
_diffrn_reflns_av_unetI/netI     0.0068
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.829
_diffrn_reflns_theta_max         28.377
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4100
_reflns_number_gt                3927
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v817 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the unambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0167P)²+2.6055P] 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     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00265(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4100
_refine_ls_number_parameters     329
_refine_ls_number_restraints     622
_refine_ls_R_factor_all          0.0184
_refine_ls_R_factor_gt           0.0173
_refine_ls_wR_factor_ref         0.0409
_refine_ls_wR_factor_gt          0.0405
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.002
_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 0.59965(2) 0.13414(2) 0.48310(2) 0.02564(5) Uani 1 1 d . . . . .
Br2 Br 0.52531(2) 0.76973(2) 0.38273(2) 0.02614(5) Uani 1 1 d . . . . .
S1 S 0.32640(3) 0.16816(4) 0.43772(2) 0.02687(8) Uani 1 1 d . . . . .
S2 S 0.72450(3) 0.43649(4) 0.31586(2) 0.02692(9) Uani 1 1 d . . . . .
C1 C 0.57599(10) 0.31535(14) 0.45258(4) 0.0162(2) Uani 1 1 d . . . . .
C2 C 0.47626(10) 0.38304(15) 0.45536(4) 0.0166(2) Uani 1 1 d . . . . .
C3 C 0.46632(10) 0.52109(15) 0.43502(5) 0.0172(2) Uani 1 1 d . . . . .
H3 H 0.401915 0.574793 0.438674 0.021 Uiso 1 1 calc R U . . .
C4 C 0.54937(10) 0.58125(14) 0.40945(4) 0.0164(2) Uani 1 1 d . . . . .
C5 C 0.64504(10) 0.50670(14) 0.40264(4) 0.0154(2) Uani 1 1 d . . . . .
C6 C 0.65832(10) 0.37511(14) 0.42706(4) 0.0154(2) Uani 1 1 d . . . . .
H6 H 0.725153 0.326095 0.426057 0.018 Uiso 1 1 calc R U . . .
C7 C 0.37942(11) 0.31117(17) 0.47584(5) 0.0234(3) Uani 1 1 d . . . . .
H7A H 0.323787 0.386436 0.481228 0.028 Uiso 1 1 calc R U . . .
H7B H 0.398210 0.267328 0.506213 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3055(15) 0.269(2) 0.3804(4) 0.0206(16) Uani 0.438(3) 1 d D U P A 1
H8A H 0.229338 0.297071 0.378175 0.025 Uiso 0.438(3) 1 calc R U P A 1
H8B H 0.347245 0.361771 0.381452 0.025 Uiso 0.438(3) 1 calc R U P A 1
C9 C 0.3359(7) 0.1869(13) 0.3358(3) 0.0231(12) Uani 0.438(3) 1 d D U P A 1
H9 H 0.283978 0.104481 0.331836 0.028 Uiso 0.438(3) 1 calc R U P A 1
C10 C 0.4483(8) 0.1209(14) 0.3335(4) 0.0242(14) Uani 0.438(3) 1 d . U P A 1
H10A H 0.476599 0.112864 0.365483 0.029 Uiso 0.438(3) 1 calc R U P A 1
H10B H 0.443139 0.020184 0.320697 0.029 Uiso 0.438(3) 1 calc R U P A 1
C11 C 0.5273(4) 0.2083(5) 0.30425(15) 0.0225(8) Uani 0.438(3) 1 d . U P A 1
H11A H 0.601201 0.180082 0.312452 0.027 Uiso 0.438(3) 1 calc R U P A 1
H11B H 0.516040 0.187074 0.270901 0.027 Uiso 0.438(3) 1 calc R U P A 1
C12 C 0.5103(3) 0.3713(4) 0.31362(16) 0.0224(7) Uani 0.438(3) 1 d D U P A 1
H12 H 0.507482 0.385961 0.348004 0.027 Uiso 0.438(3) 1 calc R U P A 1
C13 C 0.4022(8) 0.4171(13) 0.2933(5) 0.0256(13) Uani 0.438(3) 1 d . U P A 1
H13A H 0.374438 0.501936 0.311122 0.031 Uiso 0.438(3) 1 calc R U P A 1
H13B H 0.412573 0.449371 0.260799 0.031 Uiso 0.438(3) 1 calc R U P A 1
C14 C 0.3201(7) 0.2940(13) 0.2944(3) 0.0239(13) Uani 0.438(3) 1 d . U P A 1
H14A H 0.324462 0.237922 0.264972 0.029 Uiso 0.438(3) 1 calc R U P A 1
H14B H 0.247879 0.337603 0.296277 0.029 Uiso 0.438(3) 1 calc R U P A 1
C15 C 0.6001(8) 0.4674(14) 0.2942(6) 0.0205(14) Uani 0.438(3) 1 d D U P A 1
H15A H 0.581511 0.571493 0.300041 0.025 Uiso 0.438(3) 1 calc R U P A 1
H15B H 0.602632 0.453427 0.260164 0.025 Uiso 0.438(3) 1 calc R U P A 1
C8B C 0.2974(16) 0.276(2) 0.3884(5) 0.0211(18) Uani 0.422(2) 1 d D U P A 2
H8C H 0.222136 0.308493 0.389609 0.025 Uiso 0.422(2) 1 calc R U P A 2
H8D H 0.343224 0.364729 0.388419 0.025 Uiso 0.422(2) 1 calc R U P A 2
C9B C 0.3167(7) 0.1880(12) 0.3440(3) 0.0224(12) Uani 0.422(2) 1 d D U P A 2
H9B H 0.263438 0.106261 0.343024 0.027 Uiso 0.422(2) 1 calc R U P A 2
C10B C 0.4267(7) 0.1210(13) 0.3397(4) 0.0229(15) Uani 0.422(2) 1 d D U P A 2
H10C H 0.429298 0.059829 0.311316 0.027 Uiso 0.422(2) 1 calc R U P A 2
H10D H 0.439248 0.055660 0.366644 0.027 Uiso 0.422(2) 1 calc R U P A 2
C11B C 0.5157(3) 0.2347(4) 0.33754(12) 0.0229(7) Uani 0.422(2) 1 d D U P A 2
H11C H 0.585391 0.183895 0.336109 0.028 Uiso 0.422(2) 1 calc R U P A 2
H11D H 0.514368 0.295201 0.366092 0.028 Uiso 0.422(2) 1 calc R U P A 2
C12B C 0.5036(4) 0.3347(5) 0.29504(19) 0.0272(8) Uani 0.422(2) 1 d D U P A 2
H12B H 0.514587 0.275424 0.266209 0.033 Uiso 0.422(2) 1 calc R U P A 2
C13B C 0.3870(8) 0.3985(14) 0.2952(6) 0.0294(17) Uani 0.422(2) 1 d D U P A 2
H13C H 0.380859 0.470959 0.320657 0.035 Uiso 0.422(2) 1 calc R U P A 2
H13D H 0.374937 0.451421 0.265594 0.035 Uiso 0.422(2) 1 calc R U P A 2
C14B C 0.2997(8) 0.2832(14) 0.3010(4) 0.0280(15) Uani 0.422(2) 1 d D U P A 2
H14C H 0.229784 0.333132 0.303435 0.034 Uiso 0.422(2) 1 calc R U P A 2
H14D H 0.298033 0.219564 0.273164 0.034 Uiso 0.422(2) 1 calc R U P A 2
C15B C 0.5796(14) 0.4670(16) 0.2945(7) 0.0269(18) Uani 0.422(2) 1 d D U P A 2
H15C H 0.547537 0.545388 0.313833 0.032 Uiso 0.422(2) 1 calc R U P A 2
H15D H 0.583037 0.504617 0.262306 0.032 Uiso 0.422(2) 1 calc R U P A 2
C8C C 0.288(3) 0.257(4) 0.3867(12) 0.022(3) Uani 0.1399(19) 1 d D U P A 3
H8E H 0.228877 0.201463 0.372485 0.027 Uiso 0.1399(19) 1 calc R U P A 3
H8F H 0.261584 0.355931 0.394676 0.027 Uiso 0.1399(19) 1 calc R U P A 3
C9C C 0.3776(8) 0.2723(11) 0.3510(3) 0.0248(14) Uani 0.1399(19) 1 d D U P A 3
H9C H 0.429236 0.339115 0.366969 0.030 Uiso 0.1399(19) 1 calc R U P A 3
C10C C 0.4429(17) 0.129(2) 0.3449(8) 0.025(2) Uani 0.1399(19) 1 d D U P A 3
H10E H 0.467949 0.092002 0.375303 0.029 Uiso 0.1399(19) 1 calc R U P A 3
H10F H 0.399294 0.052072 0.329785 0.029 Uiso 0.1399(19) 1 calc R U P A 3
C11C C 0.5385(13) 0.1726(16) 0.3137(5) 0.0230(19) Uani 0.1399(19) 1 d D U P A 3
H11E H 0.559051 0.083387 0.296247 0.028 Uiso 0.1399(19) 1 calc R U P A 3
H11F H 0.598578 0.195296 0.334852 0.028 Uiso 0.1399(19) 1 calc R U P A 3
C12C C 0.5328(9) 0.3002(13) 0.2779(4) 0.0241(16) Uani 0.1399(19) 1 d D U P A 3
H12C H 0.572359 0.270455 0.249299 0.029 Uiso 0.1399(19) 1 calc R U P A 3
C13C C 0.4160(7) 0.3330(13) 0.2648(3) 0.0265(16) Uani 0.1399(19) 1 d D U P A 3
H13E H 0.386724 0.248504 0.247330 0.032 Uiso 0.1399(19) 1 calc R U P A 3
H13F H 0.413948 0.419941 0.244185 0.032 Uiso 0.1399(19) 1 calc R U P A 3
C14C C 0.3441(10) 0.3626(15) 0.3079(3) 0.0226(16) Uani 0.1399(19) 1 d D U P A 3
H14E H 0.347291 0.468467 0.315695 0.027 Uiso 0.1399(19) 1 calc R U P A 3
H14F H 0.269366 0.338531 0.299985 0.027 Uiso 0.1399(19) 1 calc R U P A 3
C15C C 0.580(4) 0.444(3) 0.2962(14) 0.025(3) Uani 0.1399(19) 1 d D U P A 3
H15E H 0.536067 0.477087 0.322648 0.030 Uiso 0.1399(19) 1 calc R U P A 3
H15F H 0.573966 0.518585 0.271437 0.030 Uiso 0.1399(19) 1 calc R U P A 3
C16 C 0.72801(11) 0.55123(15) 0.36781(5) 0.0208(3) Uani 1 1 d . . . . .
H16A H 0.799446 0.544033 0.382255 0.025 Uiso 1 1 calc R U . . .
H16B H 0.716275 0.654988 0.358853 0.025 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Twelve 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2016) then corrected for absorption by integration 
using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale 
the combined data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0650
0.00 0.00 1.00 0.0520
-1.00 0.00 0.00 0.1160
1.00 0.00 0.00 0.1030
1.00 1.00 -1.00 0.0690
-1.00 -1.00 1.00 0.0910
1.00 1.00 1.00 0.0630
-1.00 -1.00 -1.00 0.0790
-1.00 1.00 2.00 0.1000
1.00 -1.00 -2.00 0.1000
-2.00 2.00 -1.00 0.1080
-2.00 1.00 -2.00 0.1050
2.00 -1.00 2.00 0.1140
-1.00 -2.00 -4.00 0.0600

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 1.8924(13) . ?
Br2 C4 1.9043(13) . ?
S1 C8C 1.74(4) . ?
S1 C8B 1.76(2) . ?
S1 C7 1.8282(16) . ?
S1 C8 1.910(15) . ?
S2 C15 1.704(13) . ?
S2 C16 1.8253(15) . ?
S2 C15C 1.90(4) . ?
S2 C15B 1.938(18) . ?
C1 C6 1.3792(17) . ?
C1 C2 1.3966(18) . ?
C2 C3 1.3920(19) . ?
C2 C7 1.5004(18) . ?
C3 C4 1.3882(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3923(17) . ?
C5 C6 1.3990(18) . ?
C5 C16 1.5013(17) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.537(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.533(11) . ?
C9 C14 1.554(11) . ?
C9 H9 1.0000 . ?
C10 C11 1.525(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.523(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C15 1.532(9) . ?
C12 C13 1.534(12) . ?
C12 H12 1.0000 . ?
C13 C14 1.522(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C8B C9B 1.531(10) . ?
C8B H8C 0.9900 . ?
C8B H8D 0.9900 . ?
C9B C10B 1.513(10) . ?
C9B C14B 1.525(10) . ?
C9B H9B 1.0000 . ?
C10B C11B 1.523(10) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.533(5) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C15B 1.537(11) . ?
C12B C13B 1.573(11) . ?
C12B H12B 1.0000 . ?
C13B C14B 1.526(10) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C8C C9C 1.526(15) . ?
C8C H8E 0.9900 . ?
C8C H8F 0.9900 . ?
C9C C14C 1.546(11) . ?
C9C C10C 1.549(15) . ?
C9C H9C 1.0000 . ?
C10C C11C 1.549(16) . ?
C10C H10E 0.9900 . ?
C10C H10F 0.9900 . ?
C11C C12C 1.555(13) . ?
C11C H11E 0.9900 . ?
C11C H11F 0.9900 . ?
C12C C15C 1.526(15) . ?
C12C C13C 1.542(11) . ?
C12C H12C 1.0000 . ?
C13C C14C 1.557(12) . ?
C13C H13E 0.9900 . ?
C13C H13F 0.9900 . ?
C14C H14E 0.9900 . ?
C14C H14F 0.9900 . ?
C15C H15E 0.9900 . ?
C15C H15F 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
C8C S1 C7 106.0(12) . . ?
C8B S1 C7 99.3(6) . . ?
C7 S1 C8 103.0(5) . . ?
C15 S2 C16 103.1(6) . . ?
C16 S2 C15C 104.4(11) . . ?
C16 S2 C15B 101.6(6) . . ?
C6 C1 C2 121.81(12) . . ?
C6 C1 Br1 118.28(10) . . ?
C2 C1 Br1 119.89(10) . . ?
C3 C2 C1 117.01(12) . . ?
C3 C2 C7 119.12(12) . . ?
C1 C2 C7 123.73(13) . . ?
C4 C3 C2 120.81(12) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.95(12) . . ?
C3 C4 Br2 116.79(10) . . ?
C5 C4 Br2 121.24(10) . . ?
C4 C5 C6 116.67(11) . . ?
C4 C5 C16 124.06(12) . . ?
C6 C5 C16 118.99(11) . . ?
C1 C6 C5 121.10(12) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C2 C7 S1 111.63(10) . . ?
C2 C7 H7A 109.3 . . ?
S1 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
S1 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 S1 116.9(10) . . ?
C9 C8 H8A 108.1 . . ?
S1 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
S1 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C10 C9 C8 117.1(9) . . ?
C10 C9 C14 109.3(6) . . ?
C8 C9 C14 107.6(9) . . ?
C10 C9 H9 107.5 . . ?
C8 C9 H9 107.5 . . ?
C14 C9 H9 107.5 . . ?
C11 C10 C9 114.6(8) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 108.6(6) . . ?
C12 C11 H11A 110.0 . . ?
C10 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 C15 112.9(6) . . ?
C11 C12 C13 108.8(6) . . ?
C15 C12 C13 110.8(7) . . ?
C11 C12 H12 108.1 . . ?
C15 C12 H12 108.1 . . ?
C13 C12 H12 108.1 . . ?
C14 C13 C12 113.0(8) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C9 113.0(8) . . ?
C13 C14 H14A 109.0 . . ?
C9 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C9 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C12 C15 S2 116.5(9) . . ?
C12 C15 H15A 108.2 . . ?
S2 C15 H15A 108.2 . . ?
C12 C15 H15B 108.2 . . ?
S2 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
C9B C8B S1 110.4(12) . . ?
C9B C8B H8C 109.6 . . ?
S1 C8B H8C 109.6 . . ?
C9B C8B H8D 109.6 . . ?
S1 C8B H8D 109.6 . . ?
H8C C8B H8D 108.1 . . ?
C10B C9B C14B 106.9(7) . . ?
C10B C9B C8B 115.0(10) . . ?
C14B C9B C8B 111.0(11) . . ?
C10B C9B H9B 107.9 . . ?
C14B C9B H9B 107.9 . . ?
C8B C9B H9B 107.9 . . ?
C9B C10B C11B 113.4(8) . . ?
C9B C10B H10C 108.9 . . ?
C11B C10B H10C 108.9 . . ?
C9B C10B H10D 108.9 . . ?
C11B C10B H10D 108.9 . . ?
H10C C10B H10D 107.7 . . ?
C10B C11B C12B 111.3(6) . . ?
C10B C11B H11C 109.4 . . ?
C12B C11B H11C 109.4 . . ?
C10B C11B H11D 109.4 . . ?
C12B C11B H11D 109.4 . . ?
H11C C11B H11D 108.0 . . ?
C11B C12B C15B 114.3(8) . . ?
C11B C12B C13B 108.0(6) . . ?
C15B C12B C13B 106.7(9) . . ?
C11B C12B H12B 109.2 . . ?
C15B C12B H12B 109.2 . . ?
C13B C12B H12B 109.2 . . ?
C14B C13B C12B 114.4(8) . . ?
C14B C13B H13C 108.7 . . ?
C12B C13B H13C 108.7 . . ?
C14B C13B H13D 108.7 . . ?
C12B C13B H13D 108.7 . . ?
H13C C13B H13D 107.6 . . ?
C9B C14B C13B 112.3(9) . . ?
C9B C14B H14C 109.1 . . ?
C13B C14B H14C 109.1 . . ?
C9B C14B H14D 109.1 . . ?
C13B C14B H14D 109.1 . . ?
H14C C14B H14D 107.9 . . ?
C12B C15B S2 117.8(10) . . ?
C12B C15B H15C 107.9 . . ?
S2 C15B H15C 107.9 . . ?
C12B C15B H15D 107.9 . . ?
S2 C15B H15D 107.9 . . ?
H15C C15B H15D 107.2 . . ?
C9C C8C S1 114(2) . . ?
C9C C8C H8E 108.7 . . ?
S1 C8C H8E 108.7 . . ?
C9C C8C H8F 108.7 . . ?
S1 C8C H8F 108.7 . . ?
H8E C8C H8F 107.6 . . ?
C8C C9C C14C 113.1(19) . . ?
C8C C9C C10C 112.7(18) . . ?
C14C C9C C10C 119.9(12) . . ?
C8C C9C H9C 102.8 . . ?
C14C C9C H9C 102.8 . . ?
C10C C9C H9C 102.8 . . ?
C11C C10C C9C 105.1(15) . . ?
C11C C10C H10E 110.7 . . ?
C9C C10C H10E 110.7 . . ?
C11C C10C H10F 110.7 . . ?
C9C C10C H10F 110.7 . . ?
H10E C10C H10F 108.8 . . ?
C10C C11C C12C 122.6(14) . . ?
C10C C11C H11E 106.7 . . ?
C12C C11C H11E 106.7 . . ?
C10C C11C H11F 106.7 . . ?
C12C C11C H11F 106.7 . . ?
H11E C11C H11F 106.6 . . ?
C15C C12C C13C 107(2) . . ?
C15C C12C C11C 113.1(18) . . ?
C13C C12C C11C 110.5(10) . . ?
C15C C12C H12C 108.8 . . ?
C13C C12C H12C 108.8 . . ?
C11C C12C H12C 108.8 . . ?
C12C C13C C14C 112.8(9) . . ?
C12C C13C H13E 109.0 . . ?
C14C C13C H13E 109.0 . . ?
C12C C13C H13F 109.0 . . ?
C14C C13C H13F 109.0 . . ?
H13E C13C H13F 107.8 . . ?
C9C C14C C13C 113.0(8) . . ?
C9C C14C H14E 109.0 . . ?
C13C C14C H14E 109.0 . . ?
C9C C14C H14F 109.0 . . ?
C13C C14C H14F 109.0 . . ?
H14E C14C H14F 107.8 . . ?
C12C C15C S2 116(2) . . ?
C12C C15C H15E 108.2 . . ?
S2 C15C H15E 108.2 . . ?
C12C C15C H15F 108.2 . . ?
S2 C15C H15F 108.2 . . ?
H15E C15C H15F 107.3 . . ?
C5 C16 S2 112.13(9) . . ?
C5 C16 H16A 109.2 . . ?
S2 C16 H16A 109.2 . . ?
C5 C16 H16B 109.2 . . ?
S2 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?

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 C1 C2 C3 -6.17(19) . . . . ?
Br1 C1 C2 C3 175.44(9) . . . . ?
C6 C1 C2 C7 169.46(12) . . . . ?
Br1 C1 C2 C7 -8.92(18) . . . . ?
C1 C2 C3 C4 5.93(18) . . . . ?
C7 C2 C3 C4 -169.92(12) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 Br2 179.23(10) . . . . ?
C3 C4 C5 C6 -6.92(19) . . . . ?
Br2 C4 C5 C6 174.53(9) . . . . ?
C3 C4 C5 C16 166.93(13) . . . . ?
Br2 C4 C5 C16 -11.61(18) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
Br1 C1 C6 C5 178.22(10) . . . . ?
C4 C5 C6 C1 6.68(19) . . . . ?
C16 C5 C6 C1 -167.50(12) . . . . ?
C3 C2 C7 S1 102.65(13) . . . . ?
C1 C2 C7 S1 -72.90(15) . . . . ?
C8C S1 C7 C2 -62.4(9) . . . . ?
C8B S1 C7 C2 -60.5(6) . . . . ?
C8 S1 C7 C2 -54.7(5) . . . . ?
S1 C8 C9 C10 -52.4(14) . . . . ?
S1 C8 C9 C14 -175.9(9) . . . . ?
C8 C9 C10 C11 -102.7(10) . . . . ?
C14 C9 C10 C11 20.0(11) . . . . ?
C9 C10 C11 C12 40.9(9) . . . . ?
C10 C11 C12 C15 167.8(8) . . . . ?
C10 C11 C12 C13 -68.8(8) . . . . ?
C11 C12 C13 C14 31.4(11) . . . . ?
C15 C12 C13 C14 156.0(10) . . . . ?
C12 C13 C14 C9 30.7(12) . . . . ?
C10 C9 C14 C13 -57.8(11) . . . . ?
C8 C9 C14 C13 70.4(11) . . . . ?
C11 C12 C15 S2 -61.2(12) . . . . ?
C13 C12 C15 S2 176.6(9) . . . . ?
C16 S2 C15 C12 -86.3(10) . . . . ?
C7 S1 C8B C9B 145.5(9) . . . . ?
S1 C8B C9B C10B -54.4(13) . . . . ?
S1 C8B C9B C14B -175.9(9) . . . . ?
C14B C9B C10B C11B 60.5(10) . . . . ?
C8B C9B C10B C11B -63.3(13) . . . . ?
C9B C10B C11B C12B -61.4(9) . . . . ?
C10B C11B C12B C15B 170.8(10) . . . . ?
C10B C11B C12B C13B 52.2(8) . . . . ?
C11B C12B C13B C14B -50.3(12) . . . . ?
C15B C12B C13B C14B -173.6(12) . . . . ?
C10B C9B C14B C13B -55.9(11) . . . . ?
C8B C9B C14B C13B 70.3(12) . . . . ?
C12B C13B C14B C9B 54.0(13) . . . . ?
C11B C12B C15B S2 39.4(16) . . . . ?
C13B C12B C15B S2 158.7(11) . . . . ?
C7 S1 C8C C9C 87(2) . . . . ?
S1 C8C C9C C14C -175.2(15) . . . . ?
S1 C8C C9C C10C 45(3) . . . . ?
C8C C9C C10C C11C -172(2) . . . . ?
C14C C9C C10C C11C 52(2) . . . . ?
C9C C10C C11C C12C -28(2) . . . . ?
C10C C11C C12C C15C 98(3) . . . . ?
C10C C11C C12C C13C -22(2) . . . . ?
C15C C12C C13C C14C -70(2) . . . . ?
C11C C12C C13C C14C 53.8(14) . . . . ?
C8C C9C C14C C13C -159.3(17) . . . . ?
C10C C9C C14C C13C -22.5(18) . . . . ?
C12C C13C C14C C9C -33.3(15) . . . . ?
C13C C12C C15C S2 179.3(19) . . . . ?
C11C C12C C15C S2 58(3) . . . . ?
C16 S2 C15C C12C -141(2) . . . . ?
C4 C5 C16 S2 -102.23(13) . . . . ?
C6 C5 C16 S2 71.49(14) . . . . ?
C15 S2 C16 C5 61.4(4) . . . . ?
C15C S2 C16 C5 52.5(11) . . . . ?
C15B S2 C16 C5 58.5(5) . . . . ?

_refine_diff_density_max         0.506
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.055

