# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_h
_database_code_depnum_ccdc_archive 'CCDC 1539292'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Br N O S'
_chemical_formula_weight         155.00

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   4.914(4)
_cell_length_b                   10.850(8)
_cell_length_c                   18.952(12)
_cell_angle_alpha                74.50(8)
_cell_angle_beta                 85.40(7)
_cell_angle_gamma                84.36(9)
_cell_volume                     967.5(13)
_cell_formula_units_Z            9
_cell_measurement_temperature    566(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.394
_exptl_crystal_F_000             657
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    9.857
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      566(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9480
_diffrn_reflns_av_unetI/netI     0.0944
_diffrn_reflns_av_R_equivalents  0.1694
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.954
_diffrn_reflns_theta_max         25.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measured_fraction_theta_full 0.882
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_Laue_measured_fraction_full 0.882
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.882
_reflns_number_total             3088
_reflns_number_gt                2726
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1000P)²]
 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
_refine_ls_extinction_coef       0.56(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3088
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3183
_refine_ls_R_factor_gt           0.3135
_refine_ls_wR_factor_ref         0.7616
_refine_ls_wR_factor_gt          0.7490
_refine_ls_goodness_of_fit_ref   6.293
_refine_ls_restrained_S_all      6.293
_refine_ls_shift/su_max          0.115
_refine_ls_shift/su_mean         0.031

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 0.0804(7) 0.3732(3) 0.44881(16) 0.142(2) Uani 1 1 d . . . . .
Br2 Br 1.3143(8) -0.2945(3) 0.69075(19) 0.146(2) Uani 1 1 d . . . . .
S1 S 0.4970(19) 0.1562(7) 0.5256(4) 0.133(3) Uani 1 1 d . . . . .
S2 S 0.912(2) -0.0747(7) 0.6139(4) 0.134(3) Uani 1 1 d . . . . .
O1 O 0.492(4) 0.438(2) 0.6840(13) 0.156(8) Uani 1 1 d . . . . .
O2 O 1.225(6) 0.1597(18) 0.7701(14) 0.160(8) Uani 1 1 d . . . . .
N2 N 0.857(4) 0.2899(17) 0.7189(13) 0.123(7) Uani 1 1 d . . . . .
N1 N 0.384(6) 0.361(2) 0.5747(12) 0.153(10) Uani 1 1 d . . . . .
H1 H 0.3103 0.4332 0.5811 0.184 Uiso 1 1 calc R U . . .
C5 C 0.664(7) 0.174(3) 0.6037(13) 0.134(9) Uani 1 1 d . . . . .
C4 C 0.848(7) 0.0861(17) 0.6370(15) 0.119(7) Uani 1 1 d . . . . .
C6 C 0.595(5) 0.269(3) 0.6211(14) 0.130(9) Uani 1 1 d . . . . .
C7 C 0.638(7) 0.341(3) 0.6822(16) 0.139(9) Uani 1 1 d . . . . .
C3 C 1.027(8) 0.064(4) 0.6936(14) 0.179(18) Uani 1 1 d . . . . .
C2 C 1.152(6) -0.047(3) 0.719(2) 0.161(14) Uani 1 1 d . . . . .
H2 H 1.2401 -0.0654 0.7629 0.194 Uiso 1 1 calc R U . . .
C16 C 0.341(4) 0.3095(13) 0.5256(14) 0.137(9) Uani 1 1 d . . . . .
C8 C 1.015(7) 0.176(2) 0.7297(13) 0.129(9) Uani 1 1 d . . . . .
C9 C 0.924(4) 0.365(2) 0.7727(11) 0.101(6) Uani 1 1 d . . . . .
H9A H 1.1170 0.3480 0.7821 0.121 Uiso 1 1 calc R U . . .
H9B H 0.8892 0.4558 0.7504 0.121 Uiso 1 1 calc R U . . .
C10 C 0.761(10) 0.330(5) 0.8429(15) 0.191(17) Uani 1 1 d . . . . .
H10A H 0.7960 0.2392 0.8667 0.229 Uiso 1 1 calc R U . . .
H10B H 0.5671 0.3478 0.8349 0.229 Uiso 1 1 calc R U . . .
C11 C 0.851(8) 0.412(3) 0.8903(12) 0.150(11) Uani 1 1 d . . . . .
H11A H 0.7935 0.3745 0.9410 0.180 Uiso 1 1 calc R U . . .
H11B H 1.0499 0.4086 0.8872 0.180 Uiso 1 1 calc R U . . .
C12 C 0.742(9) 0.550(3) 0.8694(13) 0.159(12) Uani 1 1 d . . . . .
H12A H 0.8208 0.5884 0.8208 0.191 Uiso 1 1 calc R U . . .
H12B H 0.5463 0.5512 0.8649 0.191 Uiso 1 1 calc R U . . .
C17 C 1.156(5) -0.145(2) 0.6787(18) 0.150(11) Uani 1 1 d . . . . .
C13 C 0.781(9) 0.639(8) 0.917(2) 0.32(5) Uani 1 1 d . . . . .
H13A H 0.9657 0.6203 0.9333 0.382 Uiso 1 1 calc R U . . .
H13B H 0.6567 0.6171 0.9598 0.382 Uiso 1 1 calc R U . . .
C14 C 0.734(14) 0.791(6) 0.880(3) 0.32(5) Uani 1 1 d . . . . .
H14A H 0.5526 0.8081 0.8615 0.386 Uiso 1 1 calc R U . . .
H14B H 0.8641 0.8125 0.8384 0.386 Uiso 1 1 calc R U . . .
C15 C 0.763(12) 0.894(9) 0.932(3) 0.34(5) Uani 1 1 d . . . . .
H15A H 0.6629 0.9740 0.9117 0.509 Uiso 1 1 calc R U . . .
H15B H 0.9522 0.9069 0.9339 0.509 Uiso 1 1 calc R U . . .
H15C H 0.6890 0.8577 0.9813 0.509 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
Br1 C16 1.95(3) . ?
Br2 C17 1.695(18) . ?
S1 C16 1.762(14) . ?
S1 C5 1.81(2) . ?
S2 C17 1.76(3) . ?
S2 C4 1.90(2) . ?
O1 C7 1.21(4) . ?
O2 C8 1.30(4) . ?
N2 C7 1.32(3) . ?
N2 C8 1.37(3) . ?
N2 C9 1.53(3) . ?
N1 C16 1.25(3) . ?
N1 C6 1.53(4) . ?
N1 H1 0.8600 . ?
C5 C6 1.17(4) . ?
C5 C4 1.32(4) . ?
C4 C3 1.39(4) . ?
C6 C7 1.60(5) . ?
C3 C2 1.29(5) . ?
C3 C8 1.54(4) . ?
C2 C17 1.46(5) . ?
C2 H2 0.9300 . ?
C9 C10 1.47(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.54(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.50(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.51(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.61(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.70(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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 S1 C5 83.1(14) . . ?
C17 S2 C4 97.6(13) . . ?
C7 N2 C8 136(2) . . ?
C7 N2 C9 113(2) . . ?
C8 N2 C9 111(2) . . ?
C16 N1 C6 105(2) . . ?
C16 N1 H1 127.8 . . ?
C6 N1 H1 127.7 . . ?
C6 C5 C4 124(2) . . ?
C6 C5 S1 114.8(17) . . ?
C4 C5 S1 121(3) . . ?
C5 C4 C3 140(3) . . ?
C5 C4 S2 121(2) . . ?
C3 C4 S2 99(2) . . ?
C5 C6 N1 117(2) . . ?
C5 C6 C7 141.8(18) . . ?
N1 C6 C7 101(2) . . ?
O1 C7 N2 130(3) . . ?
O1 C7 C6 119(3) . . ?
N2 C7 C6 111(2) . . ?
C2 C3 C4 121(3) . . ?
C2 C3 C8 124(3) . . ?
C4 C3 C8 113(4) . . ?
C3 C2 C17 119(3) . . ?
C3 C2 H2 120.3 . . ?
C17 C2 H2 120.2 . . ?
N1 C16 S1 121(2) . . ?
N1 C16 Br1 126.7(17) . . ?
S1 C16 Br1 112.4(15) . . ?
O2 C8 N2 118.4(18) . . ?
O2 C8 C3 109(3) . . ?
N2 C8 C3 132(3) . . ?
C10 C9 N2 112(2) . . ?
C10 C9 H9A 109.1 . . ?
N2 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
N2 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 106(3) . . ?
C9 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C12 C11 C10 115(3) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 121(3) . . ?
C13 C12 H12A 107.0 . . ?
C11 C12 H12A 107.1 . . ?
C13 C12 H12B 107.0 . . ?
C11 C12 H12B 107.1 . . ?
H12A C12 H12B 106.8 . . ?
C2 C17 Br2 133(2) . . ?
C2 C17 S2 101.3(14) . . ?
Br2 C17 S2 125(2) . . ?
C12 C13 C14 118(3) . . ?
C12 C13 H13A 107.9 . . ?
C14 C13 H13A 107.8 . . ?
C12 C13 H13B 107.9 . . ?
C14 C13 H13B 108.0 . . ?
H13A C13 H13B 107.2 . . ?
C13 C14 C15 119(4) . . ?
C13 C14 H14A 107.4 . . ?
C15 C14 H14A 107.6 . . ?
C13 C14 H14B 107.6 . . ?
C15 C14 H14B 107.6 . . ?
H14A C14 H14B 107.0 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.7 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         4.015
_refine_diff_density_min         -1.070
_refine_diff_density_rms         0.276

_shelxl_version_number           2013-2

