# Electronic Supplementary Material (ESI) for Soft Matter.
# 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_FY20180116
_database_code_depnum_ccdc_archive 'CCDC 1846233'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;
_audit_creation_date             2018-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C23 H15 Br2 N O S)'
_chemical_formula_sum            'C11.5 H7.5 Br N0.5 O0.5 S0.5'
_chemical_formula_weight         256.63
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.9784(4)
_cell_length_b                   7.3112(4)
_cell_length_c                   21.0187(13)
_cell_angle_alpha                81.743(5)
_cell_angle_beta                 89.701(5)
_cell_angle_gamma                71.272(5)
_cell_volume                     1004.12(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3800
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.9240
_cell_measurement_theta_min      3.7330
_exptl_absorpt_coefficient_mu    4.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.6974
_exptl_crystal_description       plate
_exptl_crystal_F_000             507.3429
_exptl_crystal_preparation       'slow evaporation,Luminescent'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12244
_diffrn_reflns_theta_full        26.3715
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.31
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  84.00   1.00   11.01    --   17.01  57.00  60.00   84
  2  ω      6.00  73.00   1.00   11.01    --   17.01-130.00-136.00   67
  3  ω    -20.00  56.00   1.00   11.01    --   17.01 -99.00 -60.00   76
  4  ω    -10.00  85.00   1.00   11.01    --   17.01  77.00 150.00   95
  5  ω    -50.00  34.00   1.00   11.01    --   17.01 -57.00-180.00   84
  6  ω    -50.00  83.00   1.00   11.01    --   17.01   0.00-150.00  133
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0476076000
_diffrn_orient_matrix_UB_12      0.1027102000
_diffrn_orient_matrix_UB_13      -0.0058686000
_diffrn_orient_matrix_UB_21      0.0064552000
_diffrn_orient_matrix_UB_22      -0.0017566000
_diffrn_orient_matrix_UB_23      -0.0336085000
_diffrn_orient_matrix_UB_31      -0.0960852000
_diffrn_orient_matrix_UB_32      -0.0135120000
_diffrn_orient_matrix_UB_33      -0.0010152000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              -8
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2779
_reflns_number_total             4104
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.7265
_refine_diff_density_min         -0.7807
_refine_diff_density_rms         0.1521
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             6.1562
_refine_ls_goodness_of_fit_ref   1.0386
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.0386
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.1490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1012
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C8(H8), C13(H13), C7(H7), C16(H16), C9(H9), C10(H10), C17(H17),
 C1(H1), C23(H23), C20(H20), C22(H22), C19(H19), C4(H4), C3(H3)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br 0.03672(7) 0.06512(7) 0.21302(2) 0.06061(18) Uani 1.000000 .
Br2 Br 0.83097(8) 0.89926(8) -0.04489(2) 0.06661(19) Uani 1.000000 .
O1 O 1.2182(5) 0.7832(4) 0.60174(14) 0.0618(9) Uani 1.000000 .
N1 N 0.5509(5) 0.5988(4) 0.21244(14) 0.0401(8) Uani 1.000000 .
C14 C 0.3614(6) 0.1796(5) 0.25623(18) 0.0376(9) Uani 1.000000 .
H14 H 0.3919(6) 0.0646(5) 0.28532(18) 0.0451(11) Uiso 1.000000 R
C15 C 0.1986(6) 0.2323(6) 0.21302(19) 0.0381(10) Uani 1.000000 .
C5 C 0.7376(6) 0.7444(5) 0.46063(18) 0.0350(9) Uani 1.000000 .
C6 C 0.6892(6) 0.7193(5) 0.39528(17) 0.0330(9) Uani 1.000000 .
C12 C 0.4303(6) 0.4727(5) 0.21284(17) 0.0349(9) Uani 1.000000 .
C21 C 0.7454(6) 0.8073(6) 0.03612(18) 0.0433(10) Uani 1.000000 .
C11 C 0.5979(6) 0.6453(5) 0.27263(17) 0.0342(9) Uani 1.000000 .
C8 C 0.4583(6) 0.6630(5) 0.32078(18) 0.0369(9) Uani 1.000000 .
H8 H 0.3326(6) 0.6508(5) 0.31239(18) 0.0443(11) Uiso 1.000000 R
C13 C 0.4789(6) 0.3001(5) 0.25576(18) 0.0366(9) Uani 1.000000 .
H13 H 0.5907(6) 0.2655(5) 0.28424(18) 0.0439(11) Uiso 1.000000 R
C7 C 0.5031(6) 0.6981(5) 0.38053(18) 0.0367(9) Uani 1.000000 .
H7 H 0.4073(6) 0.7079(5) 0.41191(18) 0.0441(11) Uiso 1.000000 R
C2 C 0.9071(6) 0.7687(5) 0.56102(18) 0.0412(10) Uani 1.000000 .
C18 C 0.6175(6) 0.6700(5) 0.15326(17) 0.0347(9) Uani 1.000000 .
C16 C 0.1499(6) 0.4011(6) 0.16970(19) 0.0445(10) Uani 1.000000 .
H16 H 0.0403(6) 0.4332(6) 0.14048(19) 0.0534(12) Uiso 1.000000 R
C9 C 0.8248(6) 0.7086(5) 0.34614(19) 0.0409(10) Uani 1.000000 .
H9 H 0.9477(6) 0.7275(5) 0.35375(19) 0.0490(12) Uiso 1.000000 R
C10 C 0.7814(6) 0.6706(6) 0.28616(18) 0.0403(10) Uani 1.000000 .
H10 H 0.8764(6) 0.6618(6) 0.25457(18) 0.0484(12) Uiso 1.000000 R
C17 C 0.2652(6) 0.5228(5) 0.16997(18) 0.0399(10) Uani 1.000000 .
H17 H 0.2321(6) 0.6388(5) 0.14129(18) 0.0479(12) Uiso 1.000000 R
C1 C 1.0483(7) 0.7796(6) 0.6098(2) 0.0481(11) Uani 1.000000 .
H1 H 1.0030(7) 0.7842(6) 0.6514(2) 0.0577(13) Uiso 1.000000 R
C23 C 0.6528(6) 0.8483(6) 0.14333(18) 0.0405(10) Uani 1.000000 .
H23 H 0.6321(6) 0.9235(6) 0.17644(18) 0.0486(12) Uiso 1.000000 R
C20 C 0.7098(6) 0.6312(6) 0.04395(19) 0.0466(11) Uani 1.000000 .
H20 H 0.7283(6) 0.5586(6) 0.01021(19) 0.0559(13) Uiso 1.000000 R
C22 C 0.7176(6) 0.9157(6) 0.0857(2) 0.0464(11) Uani 1.000000 .
H22 H 0.7427(6) 1.0343(6) 0.0802(2) 0.0557(13) Uiso 1.000000 R
C19 C 0.6464(6) 0.5630(6) 0.10215(19) 0.0430(10) Uani 1.000000 .
H19 H 0.6226(6) 0.4438(6) 0.10741(19) 0.0516(12) Uiso 1.000000 R
C4 C 0.6198(6) 0.7482(6) 0.5127(2) 0.0497(11) Uani 1.000000 .
H4 H 0.4885(6) 0.7431(6) 0.5108(2) 0.0597(13) Uiso 1.000000 R
C3 C 0.7176(7) 0.7606(6) 0.5696(2) 0.0529(12) Uani 1.000000 .
H3 H 0.6577(7) 0.7630(6) 0.6092(2) 0.0635(14) Uiso 1.000000 R
S1 S 0.97007(16) 0.75821(15) 0.48181(5) 0.0417(3) Uani 1.000000 .


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 C15 1.912(3) . ?
Br2 C21 1.904(4) . ?
O1 C1 1.205(5) . ?
N1 C12 1.433(4) . ?
N1 C11 1.422(4) . ?
N1 C18 1.414(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(5) . ?
C14 C13 1.383(5) . ?
C15 C16 1.371(5) . ?
C5 C6 1.467(5) . ?
C5 C4 1.364(5) . ?
C5 S1 1.722(4) . ?
C6 C7 1.398(5) . ?
C6 C9 1.390(5) . ?
C12 C13 1.386(5) . ?
C12 C17 1.385(5) . ?
C21 C20 1.375(5) . ?
C21 C22 1.374(5) . ?
C11 C8 1.391(5) . ?
C11 C10 1.388(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.374(5) . ?
C13 H13 0.9300 . ?
C7 H7 0.9300 . ?
C2 C1 1.454(5) . ?
C2 C3 1.353(5) . ?
C2 S1 1.726(4) . ?
C18 C23 1.389(5) . ?
C18 C19 1.395(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(5) . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
C1 H1 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.371(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.379(5) . ?
C22 H22 0.9300 . ?
C19 H19 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.409(5) . ?
C3 H3 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
C11 N1 C12 117.5(3) . . ?
C18 N1 C12 119.2(3) . . ?
C18 N1 C11 123.3(3) . . ?
C15 C14 H14 120.5(2) . . ?
C13 C14 H14 120.5(2) . . ?
C13 C14 C15 119.0(4) . . ?
C14 C15 Br1 119.2(3) . . ?
C16 C15 Br1 119.1(3) . . ?
C16 C15 C14 121.8(3) . . ?
C4 C5 C6 127.4(3) . . ?
S1 C5 C6 121.7(3) . . ?
S1 C5 C4 110.7(3) . . ?
C7 C6 C5 120.3(3) . . ?
C9 C6 C5 122.8(3) . . ?
C9 C6 C7 116.9(3) . . ?
C13 C12 N1 120.2(3) . . ?
C17 C12 N1 119.9(3) . . ?
C17 C12 C13 119.9(3) . . ?
C20 C21 Br2 118.8(3) . . ?
C22 C21 Br2 120.7(3) . . ?
C22 C21 C20 120.5(4) . . ?
C8 C11 N1 119.7(3) . . ?
C10 C11 N1 122.4(3) . . ?
C10 C11 C8 117.9(3) . . ?
H8 C8 C11 119.4(2) . . ?
C7 C8 C11 121.1(3) . . ?
C7 C8 H8 119.4(2) . . ?
C12 C13 C14 120.0(3) . . ?
H13 C13 C14 120.0(2) . . ?
H13 C13 C12 120.0(2) . . ?
C8 C7 C6 121.6(3) . . ?
H7 C7 C6 119.2(2) . . ?
H7 C7 C8 119.2(2) . . ?
C3 C2 C1 127.2(4) . . ?
S1 C2 C1 122.0(3) . . ?
S1 C2 C3 110.8(3) . . ?
C23 C18 N1 121.9(3) . . ?
C19 C18 N1 120.3(3) . . ?
C19 C18 C23 117.8(3) . . ?
H16 C16 C15 120.4(2) . . ?
C17 C16 C15 119.2(4) . . ?
C17 C16 H16 120.4(2) . . ?
H9 C9 C6 119.1(2) . . ?
C10 C9 C6 121.7(3) . . ?
C10 C9 H9 119.1(2) . . ?
C9 C10 C11 120.8(4) . . ?
H10 C10 C11 119.6(2) . . ?
H10 C10 C9 119.6(2) . . ?
C16 C17 C12 120.2(4) . . ?
H17 C17 C12 119.9(2) . . ?
H17 C17 C16 119.9(2) . . ?
C2 C1 O1 126.5(4) . . ?
H1 C1 O1 116.7(2) . . ?
H1 C1 C2 116.7(3) . . ?
H23 C23 C18 119.3(2) . . ?
C22 C23 C18 121.3(4) . . ?
C22 C23 H23 119.3(2) . . ?
H20 C20 C21 120.2(2) . . ?
C19 C20 C21 119.6(4) . . ?
C19 C20 H20 120.2(2) . . ?
C23 C22 C21 119.8(4) . . ?
H22 C22 C21 120.1(2) . . ?
H22 C22 C23 120.1(2) . . ?
C20 C19 C18 121.0(4) . . ?
H19 C19 C18 119.5(2) . . ?
H19 C19 C20 119.5(2) . . ?
H4 C4 C5 123.5(2) . . ?
C3 C4 C5 113.0(4) . . ?
C3 C4 H4 123.5(3) . . ?
C4 C3 C2 113.5(4) . . ?
H3 C3 C2 123.3(2) . . ?
H3 C3 C4 123.3(3) . . ?
C2 S1 C5 92.01(19) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.660
_oxdiff_exptl_absorpt_empirical_full_min 0.581
