# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_tx856_sq
_database_code_depnum_ccdc_archive 'CCDC 1977315'
loop_
_audit_author_name
_audit_author_address
'Yunqi Liu'
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-02-02 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 Br N O3 S'
_chemical_formula_sum            'C30 H22 Br N O3 S'
_chemical_formula_weight         556.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOSBr
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'
H H 0.0000 0.0000 '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'

_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                   17.6100(4)
_cell_length_b                   4.47950(10)
_cell_length_c                   33.0164(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.647(2)
_cell_angle_gamma                90
_cell_volume                     2519.83(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5051
_cell_measurement_temperature    169.99(14)
_cell_measurement_theta_max      74.0720
_cell_measurement_theta_min      3.2800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.011
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            15700
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.701
_diffrn_reflns_theta_min         2.593
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  13.00   0.50    6.00    --  -46.95 100.00 -36.00  124
  2  ω    -57.00  18.00   0.50    6.00    --  -46.95  38.00  90.00  150
  3  ω    -18.00  73.00   0.50    6.00    --   46.95-100.00-141.00  182
  4  ω     31.00 108.00   0.50   15.00    --  103.25-100.00-141.00  154
  5  ω     91.00 116.00   0.50   15.00    --  103.25 -30.00-150.00   50
  6  ω    133.00 164.00   0.50   15.00    --  103.25  15.00 -90.00   62
  7  ω    111.00 137.00   0.50   15.00    --  103.25 100.00 -36.00   52
  8  ω    106.00 155.00   0.50   15.00    --  103.25  30.00 -60.00   98
  9  ω     91.00 116.00   0.50   15.00    --  103.25  15.00 -90.00   50
 10  ω     77.00 167.00   0.50   15.00    --  103.25 125.00 -90.00  180
 11  ω     36.00 100.00   0.50   15.00    --  103.25 -45.00-150.00  128
 12  ω     29.00  79.00   0.50   15.00    --  103.25 -30.00-150.00  100
 13  ω   -117.00 -71.00   0.50    6.00    --  -46.95-125.00   0.00   92
 14  ω   -149.00 -88.00   0.50   15.00    --  -99.00-100.00-141.00  122
 15  ω   -167.00-138.00   0.50   15.00    --  -99.00 -15.00  30.00   58
 16  ω   -121.00 -95.00   0.50   15.00    --  -99.00 -15.00  30.00   52
 17  ω   -106.00 -42.00   0.50   15.00    --  -99.00 100.00 -36.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0826227000
_diffrn_orient_matrix_UB_12      0.0041949000
_diffrn_orient_matrix_UB_13      -0.0077940000
_diffrn_orient_matrix_UB_21      0.0124721000
_diffrn_orient_matrix_UB_22      -0.3266364000
_diffrn_orient_matrix_UB_23      0.0147940000
_diffrn_orient_matrix_UB_31      -0.0345765000
_diffrn_orient_matrix_UB_32      -0.1076275000
_diffrn_orient_matrix_UB_33      -0.0452330000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3829
_reflns_number_total             5040
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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         1.027
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5040
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.019
_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)+(0.0871P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1295
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
;
_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
Br1 Br 0.65873(2) 0.00439(7) 0.79689(2) 0.05148(13) Uani 1 1 d . . . . .
S1 S 0.58923(4) 0.70975(15) 0.54037(2) 0.03767(16) Uani 1 1 d . . . . .
O1 O 0.38734(11) 1.0909(5) 0.53715(6) 0.0446(4) Uani 1 1 d . . . . .
O2 O 0.45241(11) 0.7699(4) 0.61654(6) 0.0462(5) Uani 1 1 d . . . . .
O3 O 0.70330(11) 0.3368(5) 0.58042(6) 0.0437(4) Uani 1 1 d . . . . .
N1 N 0.70739(12) 0.1471(5) 0.64582(7) 0.0370(5) Uani 1 1 d . . . . .
C1 C 0.50691(15) 0.9330(6) 0.51940(8) 0.0369(5) Uani 1 1 d . . . . .
C2 C 0.45791(15) 0.9447(6) 0.54746(8) 0.0369(6) Uani 1 1 d . . . . .
C3 C 0.48713(15) 0.7963(6) 0.58430(8) 0.0387(5) Uani 1 1 d . . . . .
C4 C 0.56044(14) 0.6478(6) 0.58688(8) 0.0363(5) Uani 1 1 d . . . . .
C5 C 0.60617(15) 0.4761(5) 0.61859(9) 0.0353(5) Uani 1 1 d . . . . .
C6 C 0.67583(15) 0.3197(6) 0.61114(8) 0.0367(5) Uani 1 1 d . . . . .
C7 C 0.60318(15) 0.3929(6) 0.66086(8) 0.0362(5) Uani 1 1 d . . . . .
C8 C 0.55750(17) 0.4715(6) 0.68812(9) 0.0417(6) Uani 1 1 d . . . . .
H8 H 0.516002 0.604308 0.679342 0.050 Uiso 1 1 calc R . . . .
C9 C 0.57350(16) 0.3531(7) 0.72820(9) 0.0449(6) Uani 1 1 d . . . . .
H9 H 0.542336 0.403336 0.746097 0.054 Uiso 1 1 calc R . . . .
C10 C 0.63591(16) 0.1606(7) 0.74132(9) 0.0432(6) Uani 1 1 d . . . . .
C11 C 0.68372(15) 0.0727(6) 0.71578(9) 0.0410(6) Uani 1 1 d . . . . .
H11 H 0.725063 -0.060155 0.724977 0.049 Uiso 1 1 calc R . . . .
C12 C 0.66654(14) 0.1931(6) 0.67615(8) 0.0357(5) Uani 1 1 d . . . . .
C13 C 0.32161(17) 0.8990(9) 0.52182(11) 0.0574(8) Uani 1 1 d . . . . .
H13A H 0.325347 0.810067 0.495943 0.086 Uiso 1 1 calc GR . . . .
H13B H 0.274004 1.012835 0.517226 0.086 Uiso 1 1 calc GR . . . .
H13C H 0.321283 0.744972 0.542001 0.086 Uiso 1 1 calc GR . . . .
C14 C 0.40903(19) 1.0187(6) 0.62599(10) 0.0473(7) Uani 1 1 d . . . . .
H14A H 0.355596 1.005811 0.609727 0.071 Uiso 1 1 calc GR . . . .
H14B H 0.431992 1.200797 0.619346 0.071 Uiso 1 1 calc GR . . . .
H14C H 0.410377 1.016639 0.655236 0.071 Uiso 1 1 calc GR . . . .
C15 C 0.77667(15) -0.0373(6) 0.65032(9) 0.0381(6) Uani 1 1 d . . . . .
H15A H 0.778094 -0.114250 0.623062 0.046 Uiso 1 1 calc R . . . .
H15B H 0.773126 -0.206367 0.668119 0.046 Uiso 1 1 calc R . . . .
C16 C 0.85204(15) 0.1300(6) 0.66887(9) 0.0419(6) Uani 1 1 d . . . . .
H16A H 0.848783 0.219586 0.695129 0.050 Uiso 1 1 calc R . . . .
H16B H 0.857256 0.290308 0.650014 0.050 Uiso 1 1 calc R . . . .
C17 C 0.92487(16) -0.0650(6) 0.67676(10) 0.0438(6) Uani 1 1 d . . . . .
H17A H 0.921668 -0.215229 0.697425 0.053 Uiso 1 1 calc R . . . .
H17B H 0.925780 -0.167697 0.651024 0.053 Uiso 1 1 calc R . . . .
C18 C 1.00065(16) 0.1064(7) 0.69194(10) 0.0466(6) Uani 1 1 d . . . . .
H18A H 0.998684 0.215299 0.717052 0.056 Uiso 1 1 calc R . . . .
H18B H 1.004552 0.251752 0.670786 0.056 Uiso 1 1 calc R . . . .
C19 C 1.07405(17) -0.0862(7) 0.70154(11) 0.0516(7) Uani 1 1 d . . . . .
H19A H 1.070291 -0.232454 0.722602 0.062 Uiso 1 1 calc R . . . .
H19B H 1.076603 -0.193557 0.676401 0.062 Uiso 1 1 calc R . . . .
C20 C 1.14898(18) 0.0913(9) 0.71702(14) 0.0636(9) Uani 1 1 d . . . . .
H20A H 1.154956 0.227490 0.695586 0.095 Uiso 1 1 calc GR . . . .
H20B H 1.192970 -0.042507 0.723687 0.095 Uiso 1 1 calc GR . . . .
H20C H 1.146515 0.201435 0.741597 0.095 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
Br1 C10 1.909(3) . ?
S1 C1 1.753(3) . ?
S1 C4 1.757(3) . ?
O1 C2 1.370(3) . ?
O1 C13 1.428(4) . ?
O2 C3 1.360(3) . ?
O2 C14 1.429(3) . ?
O3 C6 1.232(3) . ?
N1 C6 1.377(3) . ?
N1 C12 1.388(3) . ?
N1 C15 1.450(3) . ?
C1 C1 1.380(5) 3_676 ?
C1 C2 1.418(4) . ?
C2 C3 1.367(4) . ?
C3 C4 1.436(4) . ?
C4 C5 1.382(4) . ?
C5 C6 1.486(4) . ?
C5 C7 1.458(4) . ?
C7 C8 1.395(4) . ?
C7 C12 1.420(4) . ?
C8 C9 1.387(4) . ?
C9 C10 1.378(4) . ?
C10 C11 1.391(4) . ?
C11 C12 1.376(4) . ?
C15 C16 1.512(4) . ?
C16 C17 1.519(4) . ?
C17 C18 1.511(4) . ?
C18 C19 1.519(4) . ?
C19 C20 1.514(5) . ?

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
C1 S1 C4 92.45(13) . . ?
C2 O1 C13 113.8(2) . . ?
C3 O2 C14 118.3(2) . . ?
C6 N1 C12 110.0(2) . . ?
C6 N1 C15 123.9(2) . . ?
C12 N1 C15 125.9(2) . . ?
C1 C1 S1 123.3(3) 3_676 . ?
C1 C1 C2 126.7(3) 3_676 . ?
C2 C1 S1 110.00(19) . . ?
O1 C2 C1 121.3(2) . . ?
C3 C2 O1 124.6(2) . . ?
C3 C2 C1 114.2(2) . . ?
O2 C3 C2 126.6(2) . . ?
O2 C3 C4 119.3(2) . . ?
C2 C3 C4 114.1(2) . . ?
C3 C4 S1 109.19(19) . . ?
C5 C4 S1 120.6(2) . . ?
C5 C4 C3 130.2(2) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 C7 135.4(2) . . ?
C7 C5 C6 105.6(2) . . ?
O3 C6 N1 124.1(2) . . ?
O3 C6 C5 128.3(2) . . ?
N1 C6 C5 107.7(2) . . ?
C8 C7 C5 136.0(2) . . ?
C8 C7 C12 117.3(2) . . ?
C12 C7 C5 106.6(2) . . ?
C9 C8 C7 120.5(3) . . ?
C10 C9 C8 119.5(3) . . ?
C9 C10 Br1 119.3(2) . . ?
C9 C10 C11 122.9(3) . . ?
C11 C10 Br1 117.8(2) . . ?
C12 C11 C10 116.4(2) . . ?
N1 C12 C7 109.9(2) . . ?
C11 C12 N1 126.7(2) . . ?
C11 C12 C7 123.3(2) . . ?
N1 C15 C16 112.9(2) . . ?
C15 C16 C17 113.6(2) . . ?
C18 C17 C16 113.7(2) . . ?
C17 C18 C19 114.5(3) . . ?
C20 C19 C18 113.3(3) . . ?

_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 2.473
_oxdiff_exptl_absorpt_empirical_full_min 0.704
