# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_236_sq
_database_code_depnum_ccdc_archive 'CCDC 1877497'
_audit_update_record             
;
2018-11-07 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_audit_creation_date             2018-10-29
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H23 Br O3 S Se'
_chemical_formula_sum            'C31 H23 Br O3 S Se'
_chemical_formula_weight         634.42
_chemical_melting_point          ?
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'
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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.8543(4)
_cell_length_b                   12.8156(3)
_cell_length_c                   16.9743(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.020(3)
_cell_angle_gamma                90
_cell_volume                     3120.94(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6525
_cell_measurement_temperature    295(2)
_cell_measurement_theta_min      3.7170
_cell_measurement_theta_max      27.8520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.577
_exptl_absorpt_correction_T_min  0.69107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.39
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17250
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.255
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.6296
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4724
_reflns_number_total             6378
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+1.1719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C4(H4), C30(H30), C29(H29), C27(H27), C6(H6), C11(H11), C25(H25),
 C15(H15), C3(H3A), C21(H21), C17(H17), C7(H7), C12(H12), C20(H20), C19(H19),
 C18(H18), C14(H14), C13(H13)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Se1 Se 0.62684(3) 0.50633(3) 0.45345(2) 0.06245(15) Uani 1 1 d . . . . .
Br1 Br 0.67846(4) 1.06024(3) 0.45256(3) 0.08342(18) Uani 1 1 d . . . . .
S1 S 0.83832(5) 0.53006(5) 0.30577(4) 0.02954(17) Uani 1 1 d . . . . .
O2 O 0.93263(13) 0.55293(16) 0.35063(13) 0.0373(5) Uani 1 1 d . . . . .
O3 O 0.90156(16) 0.46866(16) 0.51736(13) 0.0421(5) Uani 1 1 d . . . . .
H3 H 0.9109 0.4558 0.4728 0.063 Uiso 1 1 calc GR . . . .
O1 O 0.79782(14) 0.59422(17) 0.23578(12) 0.0413(5) Uani 1 1 d . . . . .
C8 C 0.76970(19) 0.5381(2) 0.37774(17) 0.0284(6) Uani 1 1 d . . . . .
C22 C 0.80762(18) 0.6068(2) 0.44948(17) 0.0294(6) Uani 1 1 d . . . . .
C9 C 0.6887(2) 0.4869(2) 0.36756(18) 0.0327(6) Uani 1 1 d . . . . .
C23 C 0.77637(18) 0.7122(2) 0.44905(17) 0.0302(6) Uani 1 1 d . . . . .
C10 C 0.64052(19) 0.4215(2) 0.29781(18) 0.0346(7) Uani 1 1 d . . . . .
C31 C 0.87032(19) 0.5684(2) 0.51783(17) 0.0305(6) Uani 1 1 d . . . . .
C24 C 0.7167(2) 0.7600(2) 0.37933(19) 0.0398(7) Uani 1 1 d . . . . .
H24 H 0.6958 0.7213 0.3317 0.048 Uiso 1 1 calc R . . . .
C5 C 0.83391(19) 0.3991(2) 0.27405(18) 0.0329(6) Uani 1 1 d . . . . .
C28 C 0.80655(19) 0.7737(2) 0.52058(18) 0.0319(6) Uani 1 1 d . . . . .
C16 C 0.5258(2) 0.4094(3) 0.42144(19) 0.0406(7) Uani 1 1 d . . . . .
C4 C 0.7959(2) 0.3742(3) 0.19286(19) 0.0408(7) Uani 1 1 d . . . . .
H4 H 0.7724 0.4259 0.1547 0.049 Uiso 1 1 calc R . . . .
C30 C 0.8993(2) 0.6297(2) 0.58879(18) 0.0364(7) Uani 1 1 d . . . . .
H30 H 0.9403 0.6019 0.6350 0.044 Uiso 1 1 calc R . . . .
C29 C 0.8679(2) 0.7288(2) 0.59032(18) 0.0374(7) Uani 1 1 d . . . . .
H29 H 0.8870 0.7679 0.6379 0.045 Uiso 1 1 calc R . . . .
C27 C 0.7755(2) 0.8777(2) 0.5215(2) 0.0404(7) Uani 1 1 d . . . . .
H27 H 0.7934 0.9172 0.5690 0.048 Uiso 1 1 calc R . . . .
C6 C 0.8682(2) 0.3225(2) 0.3313(2) 0.0392(7) Uani 1 1 d . . . . .
H6 H 0.8938 0.3403 0.3856 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6366(2) 0.3138(3) 0.3063(2) 0.0455(8) Uani 1 1 d . . . . .
H11 H 0.6665 0.2826 0.3556 0.055 Uiso 1 1 calc R . . . .
C25 C 0.6894(2) 0.8612(3) 0.3808(2) 0.0479(8) Uani 1 1 d . . . . .
H25 H 0.6511 0.8916 0.3343 0.058 Uiso 1 1 calc R . . . .
C26 C 0.7195(2) 0.9196(2) 0.4529(2) 0.0460(8) Uani 1 1 d . . . . .
C15 C 0.5958(2) 0.4671(3) 0.2239(2) 0.0510(9) Uani 1 1 d . . . . .
H15 H 0.5975 0.5391 0.2173 0.061 Uiso 1 1 calc R . . . .
C3 C 0.7937(2) 0.2707(3) 0.1699(2) 0.0502(9) Uani 1 1 d . . . . .
H3A H 0.7694 0.2533 0.1153 0.060 Uiso 1 1 calc R . . . .
C21 C 0.4447(2) 0.4356(3) 0.3655(2) 0.0521(9) Uani 1 1 d . . . . .
H21 H 0.4377 0.5015 0.3417 0.063 Uiso 1 1 calc R . . . .
C17 C 0.5335(3) 0.3121(3) 0.4578(2) 0.0555(9) Uani 1 1 d . . . . .
H17 H 0.5876 0.2940 0.4969 0.067 Uiso 1 1 calc R . . . .
C2 C 0.8267(3) 0.1923(3) 0.2258(2) 0.0534(9) Uani 1 1 d . . . . .
C7 C 0.8641(2) 0.2201(3) 0.3071(2) 0.0525(9) Uani 1 1 d . . . . .
H7 H 0.8866 0.1684 0.3456 0.063 Uiso 1 1 calc R . . . .
C12 C 0.5884(3) 0.2529(3) 0.2420(3) 0.0636(11) Uani 1 1 d . . . . .
H12 H 0.5857 0.1810 0.2482 0.076 Uiso 1 1 calc R . . . .
C20 C 0.3724(3) 0.3629(4) 0.3445(2) 0.0643(11) Uani 1 1 d . . . . .
H20 H 0.3175 0.3801 0.3060 0.077 Uiso 1 1 calc R . . . .
C19 C 0.3820(3) 0.2672(4) 0.3801(3) 0.0693(12) Uani 1 1 d . . . . .
H19 H 0.3337 0.2191 0.3656 0.083 Uiso 1 1 calc R . . . .
C18 C 0.4607(3) 0.2417(3) 0.4360(3) 0.0688(11) Uani 1 1 d . . . . .
H18 H 0.4663 0.1761 0.4603 0.083 Uiso 1 1 calc R . . . .
C14 C 0.5484(3) 0.4042(4) 0.1596(2) 0.0699(12) Uani 1 1 d . . . . .
H14 H 0.5188 0.4345 0.1098 0.084 Uiso 1 1 calc R . . . .
C13 C 0.5447(3) 0.2985(4) 0.1688(3) 0.0754(14) Uani 1 1 d . . . . .
H13 H 0.5125 0.2573 0.1255 0.091 Uiso 1 1 calc R . . . .
C1 C 0.8225(4) 0.0794(3) 0.1995(3) 0.0953(16) Uani 1 1 d . . . . .
H1A H 0.7782 0.0719 0.1474 0.143 Uiso 1 1 calc GR . . . .
H1B H 0.8037 0.0369 0.2390 0.143 Uiso 1 1 calc GR . . . .
H1C H 0.8829 0.0576 0.1953 0.143 Uiso 1 1 calc GR . . . .


_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
Se1 C9 1.930(3) . ?
Se1 C16 1.915(3) . ?
Br1 C26 1.902(3) . ?
S1 O2 1.441(2) . ?
S1 O1 1.442(2) . ?
S1 C8 1.785(3) . ?
S1 C5 1.759(3) . ?
O3 H3 0.8200 . ?
O3 C31 1.360(3) . ?
C8 C22 1.490(4) . ?
C8 C9 1.342(4) . ?
C22 C23 1.428(4) . ?
C22 C31 1.377(4) . ?
C9 C10 1.475(4) . ?
C23 C24 1.420(4) . ?
C23 C28 1.419(4) . ?
C10 C11 1.390(5) . ?
C10 C15 1.388(5) . ?
C31 C30 1.409(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.362(4) . ?
C5 C4 1.384(4) . ?
C5 C6 1.381(4) . ?
C28 C29 1.415(4) . ?
C28 C27 1.413(4) . ?
C16 C21 1.368(5) . ?
C16 C17 1.384(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.380(5) . ?
C30 H30 0.9300 . ?
C30 C29 1.356(4) . ?
C29 H29 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.354(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.372(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.405(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.392(5) . ?
C3 H3A 0.9300 . ?
C3 C2 1.382(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.396(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(6) . ?
C2 C7 1.393(5) . ?
C2 C1 1.511(5) . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.374(7) . ?
C20 H20 0.9300 . ?
C20 C19 1.358(6) . ?
C19 H19 0.9300 . ?
C19 C18 1.341(6) . ?
C18 H18 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.367(7) . ?
C13 H13 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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 Se1 C9 101.15(12) . . ?
O2 S1 O1 117.42(13) . . ?
O2 S1 C8 106.02(12) . . ?
O2 S1 C5 108.05(13) . . ?
O1 S1 C8 109.92(13) . . ?
O1 S1 C5 108.52(14) . . ?
C5 S1 C8 106.37(13) . . ?
C31 O3 H3 109.5 . . ?
C22 C8 S1 115.56(19) . . ?
C9 C8 S1 122.4(2) . . ?
C9 C8 C22 122.1(3) . . ?
C23 C22 C8 120.1(2) . . ?
C31 C22 C8 120.5(3) . . ?
C31 C22 C23 119.4(3) . . ?
C8 C9 Se1 115.2(2) . . ?
C8 C9 C10 127.8(3) . . ?
C10 C9 Se1 116.92(19) . . ?
C24 C23 C22 122.9(3) . . ?
C28 C23 C22 119.4(3) . . ?
C28 C23 C24 117.7(3) . . ?
C11 C10 C9 120.3(3) . . ?
C15 C10 C9 120.4(3) . . ?
C15 C10 C11 119.2(3) . . ?
O3 C31 C22 119.2(3) . . ?
O3 C31 C30 120.0(3) . . ?
C22 C31 C30 120.7(3) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.3(3) . . ?
C25 C24 H24 119.3 . . ?
C4 C5 S1 119.9(2) . . ?
C6 C5 S1 119.0(2) . . ?
C6 C5 C4 121.1(3) . . ?
C29 C28 C23 118.8(3) . . ?
C27 C28 C23 120.1(3) . . ?
C27 C28 C29 121.0(3) . . ?
C21 C16 Se1 121.5(3) . . ?
C21 C16 C17 119.1(3) . . ?
C17 C16 Se1 119.4(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H4 120.8 . . ?
C31 C30 H30 119.7 . . ?
C29 C30 C31 120.6(3) . . ?
C29 C30 H30 119.7 . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C27 H27 120.2 . . ?
C26 C27 C28 119.6(3) . . ?
C26 C27 H27 120.2 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.4 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C24 C25 H25 120.2 . . ?
C24 C25 C26 119.6(3) . . ?
C26 C25 H25 120.2 . . ?
C27 C26 Br1 120.2(3) . . ?
C27 C26 C25 121.6(3) . . ?
C25 C26 Br1 118.2(2) . . ?
C10 C15 H15 120.3 . . ?
C10 C15 C14 119.4(4) . . ?
C14 C15 H15 120.3 . . ?
C4 C3 H3A 119.1 . . ?
C4 C3 C2 121.7(3) . . ?
C2 C3 H3A 119.1 . . ?
C16 C21 H21 120.2 . . ?
C16 C21 C20 119.6(4) . . ?
C20 C21 H21 120.2 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C3 C2 C7 118.3(3) . . ?
C3 C2 C1 120.9(4) . . ?
C7 C2 C1 120.8(4) . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 120.0 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.8 . . ?
C15 C14 H14 119.6 . . ?
C13 C14 C15 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 120.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
