# 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 
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data_jha1219b
_database_code_depnum_ccdc_archive 'CCDC 1815484'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2019-02-07 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         'C26 H24 Br N3 O3 S'
_chemical_formula_sum            'C26 H24 Br N3 O3 S'
_chemical_formula_weight         538.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

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

_cell_length_a                   17.660(2)
_cell_length_b                   17.660(2)
_cell_length_c                   13.5994(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3673.1(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    291
_cell_measurement_theta_min      12.4
_cell_measurement_theta_max      46.9

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             1656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    3.358
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_process_details   'Reqab (Higashi-Rigaku,1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku mm007HF Rapid2'
_diffrn_radiation_monochromator  'Osmic CMF Confocal mirrors'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid2 IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi partial
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            15330
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.889
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4302
_reflns_number_gt                2314
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.992

_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component 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)+(0.0330P)²+3.6724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4300
_refine_ls_number_parameters     313
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.114
_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_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
C1 C 0.4029(8) 0.8212(8) 0.3140(9) 0.066(3) Uani 1 1 d . . . . .
H1 H 0.419353 0.775538 0.305768 0.079 Uiso 1 1 calc R U . . .
O1 O 0.5152(6) 0.8826(6) 0.9080(7) 0.092(3) Uani 1 1 d . . . . .
N1 N 0.3435(6) 0.7977(6) 0.4011(7) 0.064(3) Uani 1 1 d . . . . .
S1 S 0.3221(2) 0.7901(2) 0.5965(3) 0.0715(9) Uani 1 1 d . . . . .
Br1 Br 0.16107(12) 0.87579(14) 0.14579(18) 0.1251(8) Uani 1 1 d . . . . .
N2 N 0.4690(6) 0.8708(6) 0.5038(7) 0.059(3) Uani 1 1 d . . . . .
O2 O 0.7128(5) 0.9638(5) 0.4483(6) 0.072(2) Uani 1 1 d . . . . .
C2 C 0.4871(7) 0.9096(7) 0.3322(8) 0.057(3) Uani 1 1 d . . . . .
H2 H 0.469103 0.953699 0.343537 0.068 Uiso 1 1 calc R U . . .
N3 N 0.5735(6) 0.8512(6) 0.4138(7) 0.060(2) Uani 1 1 d D . . . .
H3N H 0.548(6) 0.793(2) 0.422(8) 0.072 Uiso 1 1 d D U . . .
O3 O 0.6824(5) 0.8225(5) 0.4315(6) 0.075(2) Uani 1 1 d . . . . .
C4 C 0.5327(7) 0.9054(8) 0.4251(9) 0.060(3) Uani 1 1 d . . . . .
H4 H 0.578590 0.965521 0.442752 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3812(7) 0.8208(7) 0.4867(8) 0.052(3) Uani 1 1 d . . . . .
C6 C 0.3561(9) 0.8233(8) 0.2224(10) 0.068(3) Uani 1 1 d . . . . .
C7 C 0.2905(8) 0.8448(8) 0.2258(9) 0.064(3) Uani 1 1 d . . . . .
H7 H 0.272746 0.856508 0.286302 0.077 Uiso 1 1 calc R U . . .
C8 C 0.2507(8) 0.8488(8) 0.1378(12) 0.076(3) Uani 1 1 d . . . . .
C9 C 0.2751(10) 0.8331(10) 0.0498(12) 0.090(4) Uani 1 1 d . . . . .
H9 H 0.249860 0.839377 -0.008192 0.108 Uiso 1 1 calc R U . . .
C10 C 0.3378(10) 0.8076(10) 0.0452(11) 0.088(5) Uani 1 1 d . . . . .
H10 H 0.353013 0.793190 -0.015394 0.105 Uiso 1 1 calc R U . . .
C11 C 0.3777(8) 0.8038(8) 0.1323(11) 0.077(4) Uani 1 1 d . . . . .
H11 H 0.420697 0.787320 0.129300 0.093 Uiso 1 1 calc R U . . .
C12 C 0.4928(9) 0.8820(7) 0.6065(8) 0.061(3) Uani 1 1 d . . . . .
C13 C 0.4173(7) 0.8394(7) 0.6644(9) 0.063(3) Uani 1 1 d . . . . .
C14 C 0.4268(9) 0.8399(8) 0.7653(10) 0.074(4) Uani 1 1 d . . . . .
H14 H 0.377790 0.811167 0.806640 0.089 Uiso 1 1 calc R U . . .
C15 C 0.5110(10) 0.8840(9) 0.8040(10) 0.074(4) Uani 1 1 d . . . . .
C16 C 0.5844(8) 0.9239(8) 0.7471(9) 0.072(4) Uani 1 1 d . . . . .
H16 H 0.640115 0.951294 0.776379 0.087 Uiso 1 1 calc R U . . .
C17 C 0.5759(7) 0.9236(6) 0.6437(11) 0.067(3) Uani 1 1 d . . . . .
H17 H 0.625068 0.950733 0.602396 0.080 Uiso 1 1 calc R U . . .
C18 C 0.5995(9) 0.9330(10) 0.9541(11) 0.101(5) Uani 1 1 d . . . . .
H18L H 0.623375 0.994390 0.938374 0.152 Uiso 1 1 calc R U . . .
H18M H 0.638577 0.913497 0.930097 0.152 Uiso 1 1 calc R U . . .
H18P H 0.593148 0.925133 1.024790 0.152 Uiso 1 1 calc R U . . .
C19 C 0.5514(8) 0.9418(8) 0.2438(9) 0.075(4) Uani 1 1 d . . . . .
H19H H 0.604531 0.994856 0.262108 0.113 Uiso 1 1 calc R U . . .
H19J H 0.524367 0.953751 0.188369 0.113 Uiso 1 1 calc R U . . .
H19K H 0.565336 0.897074 0.225836 0.113 Uiso 1 1 calc R U . . .
C21 C 0.6602(9) 0.8858(10) 0.4319(9) 0.069(3) Uani 1 1 d . . . . .
C22 C 0.7723(9) 0.8518(9) 0.4651(12) 0.089(5) Uani 1 1 d . . . . .
H22D H 0.812513 0.908239 0.434834 0.106 Uiso 1 1 calc R U . . .
H22F H 0.789535 0.809477 0.444103 0.106 Uiso 1 1 calc R U . . .
C24 C 0.7171(10) 0.7993(9) 0.6353(13) 0.101(5) Uani 1 1 d . . . . .
H24 H 0.667705 0.751298 0.607483 0.122 Uiso 1 1 calc R U . . .
C25 C 0.7257(13) 0.8065(12) 0.7382(13) 0.116(6) Uani 1 1 d . . . . .
H25 H 0.682845 0.762165 0.777758 0.140 Uiso 1 1 calc R U . . .
C26 C 0.8550(14) 0.9360(14) 0.7222(15) 0.142(8) Uani 1 1 d . . . . .
H26 H 0.903395 0.984466 0.750841 0.170 Uiso 1 1 calc R U . . .
C27 C 0.8505(11) 0.9311(10) 0.6196(13) 0.112(5) Uani 1 1 d . . . . .
H27 H 0.895250 0.974714 0.581039 0.135 Uiso 1 1 calc R U . . .
C28 C 0.7791(10) 0.8608(9) 0.5755(12) 0.078(4) Uani 1 1 d . . . . .
C30 C 0.7950(16) 0.8765(13) 0.7819(15) 0.128(7) Uani 1 1 d . . . . .
H30 H 0.800084 0.882314 0.850684 0.154 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.497(14) . ?
C1 C6 1.507(17) . ?
C1 C2 1.545(15) . ?
O1 C15 1.418(15) . ?
O1 C18 1.440(15) . ?
N1 C5 1.301(13) . ?
S1 C13 1.724(11) . ?
S1 C5 1.745(11) . ?
Br1 C8 1.870(12) . ?
N2 C5 1.367(13) . ?
N2 C12 1.443(14) . ?
N2 C4 1.449(13) . ?
O2 C21 1.238(14) . ?
C2 C4 1.520(15) . ?
C2 C19 1.552(14) . ?
N3 C21 1.358(14) . ?
N3 C4 1.467(14) . ?
O3 C21 1.357(14) . ?
O3 C22 1.475(14) . ?
C6 C11 1.378(17) . ?
C6 C7 1.388(16) . ?
C7 C8 1.407(16) . ?
C8 C9 1.346(18) . ?
C9 C10 1.39(2) . ?
C10 C11 1.397(18) . ?
C12 C17 1.367(15) . ?
C12 C13 1.401(15) . ?
C13 C14 1.382(16) . ?
C14 C15 1.392(17) . ?
C15 C16 1.364(16) . ?
C16 C17 1.414(18) . ?
C22 C28 1.51(2) . ?
C24 C28 1.361(19) . ?
C24 C25 1.41(2) . ?
C25 C30 1.37(2) . ?
C26 C30 1.33(3) . ?
C26 C27 1.40(2) . ?
C27 C28 1.388(18) . ?

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
N1 C1 C6 110.1(10) . . ?
N1 C1 C2 109.9(10) . . ?
C6 C1 C2 111.7(10) . . ?
C15 O1 C18 118.0(11) . . ?
C5 N1 C1 116.3(9) . . ?
C13 S1 C5 91.2(6) . . ?
C5 N2 C12 114.3(10) . . ?
C5 N2 C4 122.5(10) . . ?
C12 N2 C4 123.1(10) . . ?
C4 C2 C1 110.5(9) . . ?
C4 C2 C19 110.7(9) . . ?
C1 C2 C19 113.9(10) . . ?
C21 N3 C4 119.9(10) . . ?
C21 O3 C22 114.4(10) . . ?
N2 C4 N3 109.5(9) . . ?
N2 C4 C2 108.4(9) . . ?
N3 C4 C2 112.9(10) . . ?
N1 C5 N2 126.3(10) . . ?
N1 C5 S1 122.3(9) . . ?
N2 C5 S1 111.3(9) . . ?
C11 C6 C7 118.1(13) . . ?
C11 C6 C1 120.3(12) . . ?
C7 C6 C1 121.6(12) . . ?
C6 C7 C8 119.4(13) . . ?
C9 C8 C7 121.7(12) . . ?
C9 C8 Br1 120.2(12) . . ?
C7 C8 Br1 118.1(11) . . ?
C8 C9 C10 119.8(14) . . ?
C9 C10 C11 118.7(15) . . ?
C6 C11 C10 122.2(13) . . ?
C17 C12 C13 123.9(12) . . ?
C17 C12 N2 126.3(12) . . ?
C13 C12 N2 109.7(10) . . ?
C14 C13 C12 118.3(11) . . ?
C14 C13 S1 128.3(10) . . ?
C12 C13 S1 113.3(9) . . ?
C13 C14 C15 118.1(12) . . ?
C16 C15 C14 123.3(13) . . ?
C16 C15 O1 122.0(12) . . ?
C14 C15 O1 114.7(12) . . ?
C15 C16 C17 119.3(12) . . ?
C12 C17 C16 117.0(12) . . ?
O2 C21 O3 123.7(12) . . ?
O2 C21 N3 125.6(13) . . ?
O3 C21 N3 110.7(12) . . ?
O3 C22 C28 111.2(11) . . ?
C28 C24 C25 121.0(17) . . ?
C30 C25 C24 121.5(19) . . ?
C30 C26 C27 124(2) . . ?
C28 C27 C26 119.0(18) . . ?
C24 C28 C27 117.7(16) . . ?
C24 C28 C22 121.4(14) . . ?
C27 C28 C22 120.9(15) . . ?
C26 C30 C25 117(2) . . ?

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 N1 C5 -158.1(10) . . . . ?
C2 C1 N1 C5 -34.7(13) . . . . ?
N1 C1 C2 C4 57.4(12) . . . . ?
C6 C1 C2 C4 179.9(10) . . . . ?
N1 C1 C2 C19 -177.3(10) . . . . ?
C6 C1 C2 C19 -54.8(14) . . . . ?
C5 N2 C4 N3 -100.8(11) . . . . ?
C12 N2 C4 N3 75.7(13) . . . . ?
C5 N2 C4 C2 22.7(14) . . . . ?
C12 N2 C4 C2 -160.7(9) . . . . ?
C21 N3 C4 N2 -115.5(11) . . . . ?
C21 N3 C4 C2 123.6(11) . . . . ?
C1 C2 C4 N2 -50.0(13) . . . . ?
C19 C2 C4 N2 -177.1(9) . . . . ?
C1 C2 C4 N3 71.5(12) . . . . ?
C19 C2 C4 N3 -55.6(13) . . . . ?
C1 N1 C5 N2 6.4(17) . . . . ?
C1 N1 C5 S1 -174.0(8) . . . . ?
C12 N2 C5 N1 -176.7(11) . . . . ?
C4 N2 C5 N1 0.1(17) . . . . ?
C12 N2 C5 S1 3.7(11) . . . . ?
C4 N2 C5 S1 -179.5(8) . . . . ?
C13 S1 C5 N1 176.8(10) . . . . ?
C13 S1 C5 N2 -3.6(8) . . . . ?
N1 C1 C6 C11 -150.4(12) . . . . ?
C2 C1 C6 C11 87.3(14) . . . . ?
N1 C1 C6 C7 29.6(16) . . . . ?
C2 C1 C6 C7 -92.8(14) . . . . ?
C11 C6 C7 C8 -2.2(18) . . . . ?
C1 C6 C7 C8 177.8(11) . . . . ?
C6 C7 C8 C9 -0.6(19) . . . . ?
C6 C7 C8 Br1 178.8(9) . . . . ?
C7 C8 C9 C10 4(2) . . . . ?
Br1 C8 C9 C10 -175.8(11) . . . . ?
C8 C9 C10 C11 -4(2) . . . . ?
C7 C6 C11 C10 2(2) . . . . ?
C1 C6 C11 C10 -178.0(13) . . . . ?
C9 C10 C11 C6 1(2) . . . . ?
C5 N2 C12 C17 175.2(10) . . . . ?
C4 N2 C12 C17 -1.6(17) . . . . ?
C5 N2 C12 C13 -1.7(12) . . . . ?
C4 N2 C12 C13 -178.4(10) . . . . ?
C17 C12 C13 C14 0.6(18) . . . . ?
N2 C12 C13 C14 177.6(10) . . . . ?
C17 C12 C13 S1 -178.1(9) . . . . ?
N2 C12 C13 S1 -1.1(11) . . . . ?
C5 S1 C13 C14 -175.9(12) . . . . ?
C5 S1 C13 C12 2.7(9) . . . . ?
C12 C13 C14 C15 1.1(18) . . . . ?
S1 C13 C14 C15 179.6(10) . . . . ?
C13 C14 C15 C16 -2(2) . . . . ?
C13 C14 C15 O1 179.1(11) . . . . ?
C18 O1 C15 C16 6.7(19) . . . . ?
C18 O1 C15 C14 -174.8(13) . . . . ?
C14 C15 C16 C17 2(2) . . . . ?
O1 C15 C16 C17 -179.5(11) . . . . ?
C13 C12 C17 C16 -1.0(17) . . . . ?
N2 C12 C17 C16 -177.4(10) . . . . ?
C15 C16 C17 C12 -0.4(18) . . . . ?
C22 O3 C21 O2 7.7(17) . . . . ?
C22 O3 C21 N3 -171.3(10) . . . . ?
C4 N3 C21 O2 -8.0(18) . . . . ?
C4 N3 C21 O3 171.0(9) . . . . ?
C21 O3 C22 C28 76.4(13) . . . . ?
C28 C24 C25 C30 2(3) . . . . ?
C30 C26 C27 C28 1(3) . . . . ?
C25 C24 C28 C27 -1(2) . . . . ?
C25 C24 C28 C22 177.5(14) . . . . ?
C26 C27 C28 C24 -1(2) . . . . ?
C26 C27 C28 C22 -178.8(15) . . . . ?
O3 C22 C28 C24 43.4(16) . . . . ?
O3 C22 C28 C27 -138.6(13) . . . . ?
C27 C26 C30 C25 0(3) . . . . ?
C24 C25 C30 C26 -2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3N N1 0.89(3) 2.16(5) 3.007(13) 158(10) 3_565 yes
N3 H3N S1 0.89(3) 2.98(8) 3.649(9) 133(9) 3_565 yes
C7 H7 O3 0.94 2.61 3.523(15) 162.9 2_665 yes
C17 H17 O2 0.94 2.55 3.419(16) 154.6 . yes

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.079




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_LJA1294B
_database_code_depnum_ccdc_archive 'CCDC 1851627'
_audit_update_record             
;
2018-06-26 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Br N2 O S'
_chemical_formula_sum            'C18 H17 Br N2 O S'
_chemical_formula_weight         389.30

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'
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'
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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.6687(7)
_cell_length_b                   8.1636(5)
_cell_length_c                   11.2423(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.070(7)
_cell_angle_gamma                90
_cell_volume                     860.75(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5102
_cell_measurement_theta_min      3.5600
_cell_measurement_theta_max      23.6510

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.514
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.36373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) mm003 X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounced mirror'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'HPAD Dectris PILATUS3R 200K'
_diffrn_reflns_number            17429
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.531
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3379
_reflns_number_gt                2860
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+0.4921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3378
_refine_ls_number_parameters     215
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_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 1.07184(8) -0.19560(9) 0.87982(7) 0.0824(3) Uani 1 1 d . . . . .
O1 O 0.6127(4) 0.5931(4) 0.3802(4) 0.0525(9) Uani 1 1 d . . . . .
H1 H 0.573(6) 0.580(8) 0.445(6) 0.065(19) Uiso 1 1 d . . . . .
S1 S 0.34481(15) 0.10682(16) 0.22432(13) 0.0503(4) Uani 1 1 d . . . . .
N6 N 0.5325(5) 0.1510(5) 0.4388(4) 0.0455(10) Uani 1 1 d . . . . .
N4 N 0.5234(4) 0.3464(5) 0.2790(4) 0.0423(10) Uani 1 1 d . . . . .
C17 C 0.3792(7) 0.5109(8) -0.0345(6) 0.0590(16) Uani 1 1 d . . . . .
H17 H 0.388909 0.598916 -0.084314 0.071 Uiso 1 1 calc R U . . .
C9 C 0.8802(7) -0.1169(7) 0.6530(6) 0.0587(16) Uani 1 1 d . . . . .
H9 H 0.909093 -0.216470 0.626886 0.070 Uiso 1 1 calc R U . . .
C2 C 0.7408(5) 0.3329(7) 0.4409(4) 0.0423(11) Uani 1 1 d . . . . .
H2 H 0.784085 0.248300 0.399794 0.051 Uiso 1 1 calc R U . . .
C18 C 0.4622(6) 0.5076(7) 0.0852(5) 0.0557(15) Uani 1 1 d . . . . .
H18A H 0.526320 0.591542 0.114857 0.067 Uiso 1 1 calc R U . . .
C5 C 0.4828(5) 0.2071(6) 0.3313(5) 0.0397(11) Uani 1 1 d . . . . .
C10 C 0.9322(6) -0.0664(7) 0.7716(5) 0.0500(14) Uani 1 1 d . . . . .
C7 C 0.7418(5) 0.1301(6) 0.6099(4) 0.0409(11) Uani 1 1 d . . . . .
C14 C 0.3460(5) 0.2561(6) 0.1134(5) 0.0417(12) Uani 1 1 d . . . . .
C11 C 0.8862(7) 0.0753(8) 0.8123(5) 0.0578(15) Uani 1 1 d . . . . .
H11 H 0.918388 0.106327 0.893953 0.069 Uiso 1 1 calc R U . . .
C1 C 0.6504(5) 0.2448(6) 0.5175(5) 0.0424(12) Uani 1 1 d . . . . .
H1A H 0.609570 0.327601 0.562111 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6490(5) 0.4399(6) 0.3417(5) 0.0403(12) Uani 1 1 d . . . . .
H3 H 0.704675 0.460290 0.281142 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2646(6) 0.2610(7) -0.0064(5) 0.0493(13) Uani 1 1 d . . . . .
H15 H 0.198118 0.179211 -0.035559 0.059 Uiso 1 1 calc R U . . .
C20 C 0.8621(6) 0.4326(8) 0.5210(6) 0.0605(16) Uani 1 1 d . . . . .
H20A H 0.825053 0.500937 0.575442 0.091 Uiso 1 1 calc R U . . .
H20B H 0.905080 0.499768 0.469753 0.091 Uiso 1 1 calc R U . . .
H20C H 0.932384 0.359589 0.568006 0.091 Uiso 1 1 calc R U . . .
C12 C 0.7910(6) 0.1726(7) 0.7309(5) 0.0544(14) Uani 1 1 d . . . . .
H12 H 0.759381 0.269536 0.758841 0.065 Uiso 1 1 calc R U . . .
C8 C 0.7847(7) -0.0188(7) 0.5726(5) 0.0537(14) Uani 1 1 d . . . . .
H8 H 0.748689 -0.053408 0.492180 0.064 Uiso 1 1 calc R U . . .
C16 C 0.2830(7) 0.3888(7) -0.0825(5) 0.0551(15) Uani 1 1 d . . . . .
C19 C 0.2012(9) 0.3918(10) -0.2150(6) 0.080(2) Uani 1 1 d . . . . .
H19A H 0.112562 0.448542 -0.222118 0.120 Uiso 0.53(9) 1 calc R U P . .
H19B H 0.182375 0.281563 -0.244274 0.120 Uiso 0.53(9) 1 calc R U P . .
H19C H 0.256386 0.447141 -0.263096 0.120 Uiso 0.53(9) 1 calc R U P . .
H19D H 0.254987 0.336289 -0.264207 0.120 Uiso 0.47(9) 1 calc R U P . .
H19E H 0.185174 0.503268 -0.242051 0.120 Uiso 0.47(9) 1 calc R U P . .
H19F H 0.111163 0.337690 -0.223229 0.120 Uiso 0.47(9) 1 calc R U P . .
C13 C 0.4473(5) 0.3777(6) 0.1587(5) 0.0420(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.902(5) . ?
O1 C3 1.395(6) . ?
S1 C14 1.746(5) . ?
S1 C5 1.765(5) . ?
N6 C5 1.273(6) . ?
N6 C1 1.476(6) . ?
N4 C5 1.380(6) . ?
N4 C13 1.396(7) . ?
N4 C3 1.462(6) . ?
C17 C16 1.380(9) . ?
C17 C18 1.389(8) . ?
C9 C10 1.369(8) . ?
C9 C8 1.381(8) . ?
C2 C3 1.521(7) . ?
C2 C20 1.527(7) . ?
C2 C1 1.546(7) . ?
C18 C13 1.373(8) . ?
C10 C11 1.357(8) . ?
C7 C12 1.372(7) . ?
C7 C8 1.382(7) . ?
C7 C1 1.513(7) . ?
C14 C15 1.385(7) . ?
C14 C13 1.401(7) . ?
C11 C12 1.381(8) . ?
C15 C16 1.388(8) . ?
C16 C19 1.508(9) . ?

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
C14 S1 C5 91.6(2) . . ?
C5 N6 C1 116.2(4) . . ?
C5 N4 C13 115.2(4) . . ?
C5 N4 C3 120.9(4) . . ?
C13 N4 C3 123.5(4) . . ?
C16 C17 C18 122.7(5) . . ?
C10 C9 C8 119.5(5) . . ?
C3 C2 C20 110.7(5) . . ?
C3 C2 C1 111.5(4) . . ?
C20 C2 C1 112.1(4) . . ?
C13 C18 C17 118.5(6) . . ?
N6 C5 N4 128.4(5) . . ?
N6 C5 S1 121.9(4) . . ?
N4 C5 S1 109.8(4) . . ?
C11 C10 C9 120.8(5) . . ?
C11 C10 Br1 119.8(4) . . ?
C9 C10 Br1 119.4(4) . . ?
C12 C7 C8 117.8(5) . . ?
C12 C7 C1 121.9(4) . . ?
C8 C7 C1 120.3(5) . . ?
C15 C14 C13 121.0(5) . . ?
C15 C14 S1 127.8(4) . . ?
C13 C14 S1 111.1(4) . . ?
C10 C11 C12 119.2(5) . . ?
N6 C1 C7 109.1(4) . . ?
N6 C1 C2 111.5(4) . . ?
C7 C1 C2 110.8(4) . . ?
O1 C3 N4 112.1(4) . . ?
O1 C3 C2 115.7(4) . . ?
N4 C3 C2 108.8(4) . . ?
C14 C15 C16 119.6(5) . . ?
C7 C12 C11 121.7(5) . . ?
C9 C8 C7 120.9(5) . . ?
C17 C16 C15 118.4(5) . . ?
C17 C16 C19 121.1(6) . . ?
C15 C16 C19 120.4(6) . . ?
C18 C13 N4 128.1(5) . . ?
C18 C13 C14 119.6(5) . . ?
N4 C13 C14 112.3(4) . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.048




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate / dichloromethane'
