# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_exp_4847
_database_code_depnum_ccdc_archive 'CCDC 1876682'
_audit_update_record             
;
2018-11-01 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 Br N O S0'
_chemical_formula_weight         466.36

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'
N N 0.0061 0.0033 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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

_cell_length_a                   16.935(3)
_cell_length_b                   7.2255(11)
_cell_length_c                   18.475(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.243(16)
_cell_angle_gamma                90.00
_cell_volume                     2247.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1375
_cell_measurement_theta_min      3.6900
_cell_measurement_theta_max      20.4680

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    1.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  Eos
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9716
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_sigmaI/netI    0.1595
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3945
_reflns_number_gt                1663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0751P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3945
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1911
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2287
_refine_ls_wR_factor_gt          0.1845
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_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
Br01 Br 0.11622(6) 1.04796(15) 0.70336(5) 0.0853(5) Uani 1 1 d . . .
O002 O 0.2535(3) 0.1636(8) 0.3889(3) 0.0685(17) Uani 1 1 d . . .
N003 N 0.2874(4) 0.5645(8) 0.5092(3) 0.0460(16) Uani 1 1 d . . .
C004 C 0.2316(4) 0.6139(11) 0.6121(4) 0.0437(19) Uani 1 1 d . . .
C005 C 0.2490(4) 0.6930(10) 0.5465(4) 0.0405(18) Uani 1 1 d . . .
C006 C 0.4091(4) 0.7606(10) 0.3736(4) 0.0447(19) Uani 1 1 d . . .
C007 C 0.3199(4) 0.5890(10) 0.4425(4) 0.0429(18) Uani 1 1 d . . .
C008 C 0.2985(4) 0.4743(10) 0.3837(4) 0.0461(19) Uani 1 1 d . . .
C009 C 0.3739(4) 0.7321(10) 0.4375(4) 0.048(2) Uani 1 1 d . . .
H009 H 0.3867 0.8097 0.4772 0.058 Uiso 1 1 calc R . .
C00A C 0.2357(5) 0.3264(11) 0.3901(4) 0.050(2) Uani 1 1 d . . .
C00B C 0.3884(4) 0.6404(11) 0.3163(4) 0.051(2) Uani 1 1 d . . .
H00B H 0.4116 0.6569 0.2733 0.061 Uiso 1 1 calc R . .
C00C C 0.1860(5) 0.9732(10) 0.5741(4) 0.055(2) Uani 1 1 d . . .
H00C H 0.1699 1.0935 0.5622 0.066 Uiso 1 1 calc R . .
C00D C 0.4648(5) 0.9156(11) 0.3677(4) 0.052(2) Uani 1 1 d . . .
C00E C 0.2614(5) 0.4304(10) 0.6139(4) 0.053(2) Uani 1 1 d . . .
H00E H 0.2582 0.3438 0.6507 0.063 Uiso 1 1 calc R . .
C00F C 0.2247(4) 0.8726(10) 0.5261(4) 0.048(2) Uani 1 1 d . . .
H00F H 0.2346 0.9218 0.4814 0.057 Uiso 1 1 calc R . .
C00G C 0.3345(5) 0.4959(10) 0.3200(4) 0.051(2) Uani 1 1 d . . .
C00H C 0.1536(5) 0.3897(12) 0.3939(4) 0.053(2) Uani 1 1 d . . .
C00I C 0.4494(5) 1.0863(11) 0.3965(5) 0.060(2) Uani 1 1 d . . .
H00I H 0.4033 1.1043 0.4188 0.072 Uiso 1 1 calc R . .
C00J C 0.1704(4) 0.8983(12) 0.6406(4) 0.052(2) Uani 1 1 d . . .
C00K C 0.2953(5) 0.4058(11) 0.5515(4) 0.060(2) Uani 1 1 d . . .
H00K H 0.3204 0.2978 0.5389 0.072 Uiso 1 1 calc R . .
C00L C 0.1913(5) 0.7220(12) 0.6601(4) 0.061(2) Uani 1 1 d . . .
H00L H 0.1792 0.6736 0.7042 0.073 Uiso 1 1 calc R . .
C00M C 0.0983(6) 0.2553(13) 0.4082(5) 0.077(3) Uani 1 1 d . . .
H00M H 0.1141 0.1325 0.4145 0.092 Uiso 1 1 calc R . .
C00N C 0.5031(5) 1.2328(12) 0.3923(5) 0.071(3) Uani 1 1 d . . .
H00N H 0.4934 1.3463 0.4134 0.085 Uiso 1 1 calc R . .
C00O C 0.3146(5) 0.3713(12) 0.2558(4) 0.078(3) Uani 1 1 d . . .
H00A H 0.3380 0.2517 0.2660 0.116 Uiso 1 1 calc R . .
H00D H 0.3352 0.4233 0.2139 0.116 Uiso 1 1 calc R . .
H00G H 0.2580 0.3589 0.2464 0.116 Uiso 1 1 calc R . .
C00P C 0.1291(5) 0.5712(13) 0.3860(5) 0.069(3) Uani 1 1 d . . .
H00P H 0.1661 0.6622 0.3785 0.082 Uiso 1 1 calc R . .
C00Q C 0.5317(6) 0.8961(14) 0.3332(5) 0.083(3) Uani 1 1 d . . .
H00Q H 0.5424 0.7834 0.3119 0.099 Uiso 1 1 calc R . .
C00R C 0.5677(6) 1.2103(15) 0.3584(5) 0.075(3) Uani 1 1 d . . .
H00R H 0.6021 1.3090 0.3542 0.090 Uiso 1 1 calc R . .
C00S C 0.5834(6) 1.0420(18) 0.3297(6) 0.099(4) Uani 1 1 d . . .
H00S H 0.6296 1.0257 0.3075 0.119 Uiso 1 1 calc R . .
C00T C 0.0209(7) 0.3037(18) 0.4132(6) 0.104(4) Uani 1 1 d . . .
H00T H -0.0158 0.2146 0.4237 0.125 Uiso 1 1 calc R . .
C00U C -0.0022(7) 0.486(2) 0.4024(7) 0.115(4) Uani 1 1 d . . .
H00U H -0.0550 0.5184 0.4045 0.138 Uiso 1 1 calc R . .
C00V C 0.0513(7) 0.6207(17) 0.3888(6) 0.105(4) Uani 1 1 d . . .
H00V H 0.0353 0.7430 0.3815 0.126 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
Br01 C00J 1.894(8) . ?
O002 C00A 1.215(8) . ?
N003 C005 1.363(8) . ?
N003 C00K 1.386(9) . ?
N003 C007 1.414(8) . ?
C004 C005 1.401(9) . ?
C004 C00L 1.411(10) . ?
C004 C00E 1.418(10) . ?
C005 C00F 1.401(10) . ?
C006 C00B 1.384(10) . ?
C006 C009 1.395(9) . ?
C006 C00D 1.476(10) . ?
C007 C008 1.383(10) . ?
C007 C009 1.390(9) . ?
C008 C00G 1.392(9) . ?
C008 C00A 1.521(10) . ?
C009 H009 0.9300 . ?
C00A C00H 1.473(11) . ?
C00B C00G 1.394(10) . ?
C00B H00B 0.9300 . ?
C00C C00F 1.368(9) . ?
C00C C00J 1.394(10) . ?
C00C H00C 0.9300 . ?
C00D C00Q 1.367(10) . ?
C00D C00I 1.379(10) . ?
C00E C00K 1.354(10) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G C00O 1.498(10) . ?
C00H C00P 1.379(11) . ?
C00H C00M 1.394(11) . ?
C00I C00N 1.403(10) . ?
C00I H00I 0.9300 . ?
C00J C00L 1.360(10) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M C00T 1.369(13) . ?
C00M H00M 0.9300 . ?
C00N C00R 1.328(12) . ?
C00N H00N 0.9300 . ?
C00O H00A 0.9600 . ?
C00O H00D 0.9600 . ?
C00O H00G 0.9600 . ?
C00P C00V 1.370(12) . ?
C00P H00P 0.9300 . ?
C00Q C00S 1.376(12) . ?
C00Q H00Q 0.9300 . ?
C00R C00S 1.364(12) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00T C00U 1.384(14) . ?
C00T H00T 0.9300 . ?
C00U C00V 1.370(14) . ?
C00U H00U 0.9300 . ?
C00V H00V 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
C005 N003 C00K 107.5(6) . . ?
C005 N003 C007 127.4(6) . . ?
C00K N003 C007 124.9(6) . . ?
C005 C004 C00L 118.6(7) . . ?
C005 C004 C00E 107.0(6) . . ?
C00L C004 C00E 134.3(7) . . ?
N003 C005 C00F 129.6(6) . . ?
N003 C005 C004 108.5(6) . . ?
C00F C005 C004 121.9(7) . . ?
C00B C006 C009 117.3(7) . . ?
C00B C006 C00D 122.0(7) . . ?
C009 C006 C00D 120.6(7) . . ?
C008 C007 C009 120.8(7) . . ?
C008 C007 N003 121.0(6) . . ?
C009 C007 N003 118.2(6) . . ?
C007 C008 C00G 119.8(7) . . ?
C007 C008 C00A 119.1(6) . . ?
C00G C008 C00A 121.2(7) . . ?
C007 C009 C006 120.7(7) . . ?
C007 C009 H009 119.6 . . ?
C006 C009 H009 119.6 . . ?
O002 C00A C00H 122.6(7) . . ?
O002 C00A C008 120.1(7) . . ?
C00H C00A C008 117.2(7) . . ?
C006 C00B C00G 123.0(7) . . ?
C006 C00B H00B 118.5 . . ?
C00G C00B H00B 118.5 . . ?
C00F C00C C00J 121.0(7) . . ?
C00F C00C H00C 119.5 . . ?
C00J C00C H00C 119.5 . . ?
C00Q C00D C00I 118.3(8) . . ?
C00Q C00D C006 121.6(8) . . ?
C00I C00D C006 120.1(7) . . ?
C00K C00E C004 106.6(6) . . ?
C00K C00E H00E 126.7 . . ?
C004 C00E H00E 126.7 . . ?
C00C C00F C005 117.7(7) . . ?
C00C C00F H00F 121.2 . . ?
C005 C00F H00F 121.2 . . ?
C008 C00G C00B 118.3(7) . . ?
C008 C00G C00O 121.4(7) . . ?
C00B C00G C00O 120.2(7) . . ?
C00P C00H C00M 118.8(8) . . ?
C00P C00H C00A 124.4(8) . . ?
C00M C00H C00A 116.7(8) . . ?
C00D C00I C00N 120.2(8) . . ?
C00D C00I H00I 119.9 . . ?
C00N C00I H00I 119.9 . . ?
C00L C00J C00C 121.9(7) . . ?
C00L C00J Br01 120.1(6) . . ?
C00C C00J Br01 118.0(6) . . ?
C00E C00K N003 110.4(7) . . ?
C00E C00K H00K 124.8 . . ?
N003 C00K H00K 124.8 . . ?
C00J C00L C004 118.8(7) . . ?
C00J C00L H00L 120.6 . . ?
C004 C00L H00L 120.6 . . ?
C00T C00M C00H 120.2(10) . . ?
C00T C00M H00M 119.9 . . ?
C00H C00M H00M 119.9 . . ?
C00R C00N C00I 120.3(9) . . ?
C00R C00N H00N 119.8 . . ?
C00I C00N H00N 119.8 . . ?
C00G C00O H00A 109.5 . . ?
C00G C00O H00D 109.5 . . ?
H00A C00O H00D 109.5 . . ?
C00G C00O H00G 109.5 . . ?
H00A C00O H00G 109.5 . . ?
H00D C00O H00G 109.5 . . ?
C00V C00P C00H 121.6(9) . . ?
C00V C00P H00P 119.2 . . ?
C00H C00P H00P 119.2 . . ?
C00D C00Q C00S 120.4(9) . . ?
C00D C00Q H00Q 119.8 . . ?
C00S C00Q H00Q 119.8 . . ?
C00N C00R C00S 119.9(9) . . ?
C00N C00R H00R 120.1 . . ?
C00S C00R H00R 120.1 . . ?
C00R C00S C00Q 120.8(10) . . ?
C00R C00S H00S 119.6 . . ?
C00Q C00S H00S 119.6 . . ?
C00M C00T C00U 119.4(10) . . ?
C00M C00T H00T 120.3 . . ?
C00U C00T H00T 120.3 . . ?
C00V C00U C00T 121.3(11) . . ?
C00V C00U H00U 119.3 . . ?
C00T C00U H00U 119.3 . . ?
C00P C00V C00U 118.6(11) . . ?
C00P C00V H00V 120.7 . . ?
C00U C00V H00V 120.7 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.075
