# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_srk_sp_2_21_autored
_database_code_depnum_ccdc_archive 'CCDC 2168016'
loop_
_audit_author_name
_audit_author_address
'Darshan S. Mhatre'
;IIT Bombay
India
;
_audit_update_record             
;
2022-04-21 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-09-29
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1,2-bis(4-bromobenzyl)thio)ethane
_chemical_formula_moiety         'C8 H8 Br S'
_chemical_formula_sum            'C8 H8 Br S'
_chemical_formula_weight         216.11
_chemical_melting_point          367-369
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'
S S 0.1246 0.1234 '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                   16.6134(6)
_cell_length_b                   5.5697(2)
_cell_length_c                   9.1693(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.329(4)
_cell_angle_gamma                90
_cell_volume                     822.06(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2004
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.0400
_cell_measurement_theta_min      2.5220
_shelx_estimated_absorpt_T_max   0.566
_shelx_estimated_absorpt_T_min   0.217
_exptl_absorpt_coefficient_mu    5.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.124
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4332
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.531
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -38.01 156.99   1.00    2.00   6.61  -9.84 -31.50    --   195
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0100452000
_diffrn_orient_matrix_UB_12      -0.0116083000
_diffrn_orient_matrix_UB_13      0.0705122000
_diffrn_orient_matrix_UB_21      -0.0425743000
_diffrn_orient_matrix_UB_22      -0.0128133000
_diffrn_orient_matrix_UB_23      -0.0373677000
_diffrn_orient_matrix_UB_31      0.0053136000
_diffrn_orient_matrix_UB_32      -0.1261381000
_diffrn_orient_matrix_UB_33      -0.0026820000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1203
_reflns_number_total             1385
_reflns_odcompleteness_completeness 75.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.71
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.338
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0264
_refine_ls_restrained_S_all      1.076
_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)+(0.0267P)²+0.2549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0631
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C005(H00A,H00B), C00A(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C007(H007), C008(H008), C009(H009)
;
_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
Br01 Br 0.92650(2) 0.29688(6) 0.64924(4) 0.03956(14) Uani 1 1 d . . . . .
S002 S 0.57004(4) 0.79183(13) 0.19751(8) 0.02504(19) Uani 1 1 d . . . . .
C003 C 0.72134(17) 0.5895(5) 0.2441(3) 0.0217(6) Uani 1 1 d . . . . .
C004 C 0.77187(18) 0.2850(5) 0.4318(3) 0.0252(6) Uani 1 1 d . . . . .
H004 H 0.764792 0.135548 0.476956 0.030 Uiso 1 1 calc R . . . .
C005 C 0.49144(17) 0.8794(5) 0.0304(3) 0.0223(6) Uani 1 1 d . . . . .
H00A H 0.488574 0.756317 -0.048636 0.027 Uiso 1 1 calc R . . . .
H00B H 0.436668 0.884567 0.054843 0.027 Uiso 1 1 calc R . . . .
C006 C 0.84256(17) 0.4202(5) 0.4857(3) 0.0245(6) Uani 1 1 d . . . . .
C007 C 0.71146(17) 0.3709(5) 0.3109(3) 0.0235(6) Uani 1 1 d . . . . .
H007 H 0.662543 0.279172 0.272886 0.028 Uiso 1 1 calc R . . . .
C008 C 0.79292(18) 0.7207(5) 0.3013(3) 0.0262(7) Uani 1 1 d . . . . .
H008 H 0.800299 0.870404 0.256657 0.031 Uiso 1 1 calc R . . . .
C009 C 0.85415(18) 0.6377(5) 0.4227(3) 0.0286(7) Uani 1 1 d . . . . .
H009 H 0.903030 0.729163 0.461544 0.034 Uiso 1 1 calc R . . . .
C00A C 0.65366(18) 0.6869(5) 0.1170(3) 0.0275(7) Uani 1 1 d . . . . .
H00C H 0.633055 0.559748 0.041624 0.033 Uiso 1 1 calc R . . . .
H00D H 0.675181 0.821112 0.066797 0.033 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.0293(2) 0.0547(2) 0.0302(2) 0.00660(14) -0.00108(14) 0.01055(14)
S002 0.0250(4) 0.0346(4) 0.0159(4) 0.0051(3) 0.0058(3) 0.0062(3)
C003 0.0224(15) 0.0264(15) 0.0183(15) -0.0015(11) 0.0084(12) 0.0035(11)
C004 0.0295(17) 0.0229(15) 0.0260(17) 0.0002(12) 0.0121(14) 0.0027(12)
C005 0.0186(15) 0.0306(15) 0.0170(15) 0.0008(11) 0.0029(12) 0.0012(11)
C006 0.0241(16) 0.0316(16) 0.0174(15) 0.0007(12) 0.0046(12) 0.0075(12)
C007 0.0225(15) 0.0261(15) 0.0216(16) -0.0029(11) 0.0049(12) -0.0013(11)
C008 0.0306(17) 0.0228(16) 0.0282(17) 0.0026(12) 0.0128(14) 0.0019(12)
C009 0.0239(16) 0.0318(17) 0.0309(18) -0.0063(13) 0.0083(14) -0.0044(12)
C00A 0.0277(16) 0.0342(17) 0.0218(16) 0.0031(12) 0.0086(13) 0.0047(13)

_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 C006 1.905(3) . ?
S002 C005 1.817(3) . ?
S002 C00A 1.823(3) . ?
C003 C007 1.391(4) . ?
C003 C008 1.384(4) . ?
C003 C00A 1.506(4) . ?
C004 C006 1.379(4) . ?
C004 C007 1.384(4) . ?
C005 C005 1.508(5) 3_675 ?
C006 C009 1.376(4) . ?
C008 C009 1.388(4) . ?

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 S002 C00A 101.85(13) . . ?
C007 C003 C00A 120.6(3) . . ?
C008 C003 C007 118.7(3) . . ?
C008 C003 C00A 120.7(3) . . ?
C006 C004 C007 118.9(3) . . ?
C005 C005 S002 112.9(2) 3_675 . ?
C004 C006 Br01 118.5(2) . . ?
C009 C006 Br01 119.8(2) . . ?
C009 C006 C004 121.7(3) . . ?
C004 C007 C003 120.9(3) . . ?
C003 C008 C009 121.2(3) . . ?
C006 C009 C008 118.6(3) . . ?
C003 C00A S002 107.46(19) . . ?

_shelx_res_file                  
;
TITL srk_sp_2_21_autored_a.res in P2(1)/c
    srk_sp_2_21_autored.res
    created by SHELXL-2018/3 at 16:40:55 on 29-Sep-2021
REM Old TITL srk_sp_2_21_autored_a.res in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.234, Rweak 0.005, Alpha 0.022
REM <I/s> 0.563 for 177 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 O Br
CELL 0.71073 16.6134 5.5697 9.1693 90 104.329 90
ZERR 4 0.0006 0.0002 0.0004 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br S
UNIT 32 32 4 4

L.S. 20
PLAN  2 0 0
SIZE 0.124 0.245 0.426
TEMP -123
BOND
list 4
fmap 2
acta
OMIT -3 50
OMIT -4 6 3
REM <olex2.extras>
REM <HklSrc "%.\\SRK_SP_2_21_autored.hkl">
REM </olex2.extras>

WGHT    0.026700    0.254900
FVAR       0.77254
BR01  3    0.926496    0.296884    0.649243    11.00000    0.02931    0.05473 =
         0.03019    0.00660   -0.00108    0.01055
S002  4    0.570038    0.791827    0.197511    11.00000    0.02496    0.03461 =
         0.01594    0.00506    0.00578    0.00616
C003  1    0.721340    0.589525    0.244143    11.00000    0.02235    0.02639 =
         0.01827   -0.00148    0.00842    0.00353
C004  1    0.771875    0.285023    0.431801    11.00000    0.02951    0.02287 =
         0.02605    0.00016    0.01212    0.00270
AFIX  43
H004  2    0.764792    0.135548    0.476956    11.00000   -1.20000
AFIX   0
C005  1    0.491438    0.879397    0.030383    11.00000    0.01857    0.03061 =
         0.01702    0.00076    0.00288    0.00116
AFIX  23
H00A  2    0.488574    0.756317   -0.048636    11.00000   -1.20000
H00B  2    0.436668    0.884567    0.054843    11.00000   -1.20000
AFIX   0
C006  1    0.842558    0.420200    0.485663    11.00000    0.02415    0.03162 =
         0.01742    0.00072    0.00463    0.00747
C007  1    0.711459    0.370881    0.310866    11.00000    0.02247    0.02608 =
         0.02155   -0.00291    0.00493   -0.00134
AFIX  43
H007  2    0.662543    0.279172    0.272886    11.00000   -1.20000
AFIX   0
C008  1    0.792915    0.720731    0.301311    11.00000    0.03061    0.02279 =
         0.02815    0.00261    0.01282    0.00194
AFIX  43
H008  2    0.800299    0.870404    0.256657    11.00000   -1.20000
AFIX   0
C009  1    0.854152    0.637700    0.422735    11.00000    0.02395    0.03179 =
         0.03088   -0.00633    0.00829   -0.00443
AFIX  43
H009  2    0.903030    0.729163    0.461544    11.00000   -1.20000
AFIX   0
C00A  1    0.653661    0.686938    0.117045    11.00000    0.02770    0.03423 =
         0.02176    0.00313    0.00863    0.00469
AFIX  23
H00C  2    0.633055    0.559748    0.041624    11.00000   -1.20000
H00D  2    0.675181    0.821112    0.066797    11.00000   -1.20000
AFIX   0
HKLF 4




REM  srk_sp_2_21_autored_a.res in P2(1)/c
REM wR2 = 0.0631, GooF = S = 1.076, Restrained GooF = 1.076 for all data
REM R1 = 0.0264 for 1203 Fo > 4sig(Fo) and 0.0341 for all 1385 data
REM 91 parameters refined using 0 restraints

END

WGHT      0.0266      0.2514

REM Highest difference peak  0.338,  deepest hole -0.404,  1-sigma level  0.066
Q1    1   0.9777  0.3231  0.6087  11.00000  0.05    0.34
Q2    1   0.9723  0.2303  0.6292  11.00000  0.05    0.32
;
_shelx_res_checksum              57636
_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 1.190
_oxdiff_exptl_absorpt_empirical_full_min 0.837
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and petroleum ether'
####################################################################### 
# 
# 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_fastscan_autored
_database_code_depnum_ccdc_archive 'CCDC 2168017'
loop_
_audit_author_name
_audit_author_address
'Darshan S. Mhatre'
;IIT Bombay
India
;
_audit_update_record             
;
2022-04-21 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-06-30
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        (E)-1,4-bis((4-bromobenzyl)thio)but-2-ene
_chemical_formula_moiety         'C9 H9 Br S'
_chemical_formula_sum            'C9 H9 Br S'
_chemical_formula_weight         229.13
_chemical_melting_point          357-359
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'
S S 0.1246 0.1234 '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                   16.5752(12)
_cell_length_b                   6.3230(6)
_cell_length_c                   9.1422(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.622(8)
_cell_angle_gamma                90
_cell_volume                     941.73(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1344
_cell_measurement_temperature    304.00(10)
_cell_measurement_theta_max      24.5240
_cell_measurement_theta_min      3.7400
_shelx_estimated_absorpt_T_max   0.487
_shelx_estimated_absorpt_T_min   0.371
_exptl_absorpt_coefficient_mu    4.520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.186
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5115
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.456
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      304.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -25.75 154.25   1.00    4.00 -25.75   0.00  73.76    --   180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0032916000
_diffrn_orient_matrix_UB_12      0.0931128000
_diffrn_orient_matrix_UB_13      -0.0437786000
_diffrn_orient_matrix_UB_21      -0.0356946000
_diffrn_orient_matrix_UB_22      0.0295917000
_diffrn_orient_matrix_UB_23      0.0276574000
_diffrn_orient_matrix_UB_31      0.0246832000
_diffrn_orient_matrix_UB_32      0.0551535000
_diffrn_orient_matrix_UB_33      0.0595690000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1285
_reflns_number_total             1641
_reflns_odcompleteness_completeness 83.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.66
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.401
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+0.4977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0800
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C2(H2), C5(H5), C6(H6)
;
_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
Br2 Br 0.92918(2) 0.26883(8) 0.27619(5) 0.0854(2) Uani 1 1 d . . . . .
S2 S 0.62431(5) 0.90054(13) 0.52417(11) 0.0589(3) Uani 1 1 d . . . . .
C4 C 0.75141(17) 0.6088(5) 0.5397(3) 0.0412(7) Uani 1 1 d . . . . .
C3 C 0.73437(19) 0.4081(5) 0.4813(3) 0.0494(8) Uani 1 1 d . . . . .
H3 H 0.687148 0.338869 0.496693 0.059 Uiso 1 1 calc R . . . .
C9 C 0.50063(18) 0.6038(5) 0.4952(3) 0.0440(7) Uani 1 1 d . . . . .
H9 H 0.466515 0.679095 0.546537 0.053 Uiso 1 1 calc R . . . .
C1 C 0.85605(18) 0.4109(5) 0.3788(3) 0.0489(8) Uani 1 1 d . . . . .
C2 C 0.7860(2) 0.3091(5) 0.4008(4) 0.0536(8) Uani 1 1 d . . . . .
H2 H 0.773589 0.174707 0.361714 0.064 Uiso 1 1 calc R . . . .
C5 C 0.82257(19) 0.7069(5) 0.5146(4) 0.0495(8) Uani 1 1 d . . . . .
H5 H 0.835232 0.841536 0.553028 0.059 Uiso 1 1 calc R . . . .
C6 C 0.87469(19) 0.6107(6) 0.4349(3) 0.0525(8) Uani 1 1 d . . . . .
H6 H 0.921924 0.679363 0.418945 0.063 Uiso 1 1 calc R . . . .
C7 C 0.6951(2) 0.7142(5) 0.6283(4) 0.0535(8) Uani 1 1 d . . . . .
H7A H 0.728112 0.787512 0.711612 0.064 Uiso 1 1 calc R . . . .
H7B H 0.663898 0.606015 0.668507 0.064 Uiso 1 1 calc R . . . .
C8 C 0.55201(19) 0.7278(5) 0.4091(4) 0.0510(8) Uani 1 1 d . . . . .
H8A H 0.516436 0.812284 0.335339 0.061 Uiso 1 1 calc R . . . .
H8B H 0.581978 0.630897 0.356563 0.061 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br2 0.0580(3) 0.1178(4) 0.0813(3) -0.0330(3) 0.0156(2) 0.0147(2)
S2 0.0544(5) 0.0386(5) 0.0879(6) -0.0027(4) 0.0240(5) -0.0020(4)
C4 0.0366(16) 0.0468(17) 0.0381(15) 0.0015(13) 0.0012(13) -0.0002(13)
C3 0.0423(17) 0.0446(18) 0.060(2) 0.0035(15) 0.0061(15) -0.0106(14)
C9 0.0387(15) 0.0516(16) 0.0422(15) 0.0002(15) 0.0089(12) 0.0021(15)
C1 0.0408(17) 0.061(2) 0.0427(17) -0.0035(15) 0.0014(14) 0.0083(15)
C2 0.0484(19) 0.0429(18) 0.067(2) -0.0059(16) 0.0027(16) 0.0008(15)
C5 0.0473(18) 0.0446(18) 0.0541(18) -0.0045(15) 0.0028(15) -0.0091(15)
C6 0.0386(17) 0.064(2) 0.0540(19) -0.0008(16) 0.0069(15) -0.0118(16)
C7 0.0465(18) 0.064(2) 0.0494(18) -0.0067(16) 0.0066(14) -0.0028(16)
C8 0.0471(18) 0.054(2) 0.0521(18) 0.0104(15) 0.0102(15) 0.0039(15)

_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
Br2 C1 1.891(3) . ?
S2 C7 1.805(3) . ?
S2 C8 1.809(3) . ?
C4 C3 1.385(4) . ?
C4 C5 1.389(4) . ?
C4 C7 1.500(4) . ?
C3 C2 1.378(4) . ?
C9 C9 1.316(6) 3_666 ?
C9 C8 1.486(4) . ?
C1 C2 1.374(4) . ?
C1 C6 1.377(5) . ?
C5 C6 1.371(4) . ?

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
C7 S2 C8 102.08(15) . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C7 120.8(3) . . ?
C5 C4 C7 121.5(3) . . ?
C2 C3 C4 121.3(3) . . ?
C9 C9 C8 125.4(4) 3_666 . ?
C2 C1 Br2 119.1(3) . . ?
C2 C1 C6 120.8(3) . . ?
C6 C1 Br2 120.0(2) . . ?
C1 C2 C3 119.3(3) . . ?
C6 C5 C4 121.8(3) . . ?
C5 C6 C1 119.0(3) . . ?
C4 C7 S2 114.4(2) . . ?
C9 C8 S2 113.2(2) . . ?

_shelx_res_file                  
;
TITL fastscan_autored_a.res in P2(1)/c
    fastscan_autored.res
    created by SHELXL-2018/3 at 19:42:12 on 30-Jun-2021
REM Old TITL fastscan_autored in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.303, Rweak 0.253, Alpha 0.047
REM <I/s> 0.372 for 184 systematic absences, Orientation as input
REM Formula found by SHELXT: C9 O Br
CELL 0.71073 16.5752 6.323 9.1422 90 100.622 90
ZERR 4 0.0012 0.0006 0.0008 0 0.008 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br S
UNIT 36 36 4 4

L.S. 20
PLAN  5 0 0
SIZE 0.186 0.27 0.274
TEMP 31
BOND
list 4
fmap 2
acta
OMIT -3 50
OMIT 2 0 0
REM <olex2.extras>
REM <HklSrc "%.\\fastscan_autored.hkl">
REM </olex2.extras>

WGHT    0.027000    0.497700
FVAR       0.92516
BR2   3    0.929182    0.268834    0.276190    11.00000    0.05804    0.11784 =
         0.08135   -0.03302    0.01559    0.01471
S2    4    0.624309    0.900536    0.524166    11.00000    0.05441    0.03858 =
         0.08786   -0.00270    0.02401   -0.00196
C4    1    0.751405    0.608756    0.539665    11.00000    0.03660    0.04680 =
         0.03814    0.00147    0.00115   -0.00022
C3    1    0.734369    0.408109    0.481263    11.00000    0.04228    0.04464 =
         0.05998    0.00347    0.00613   -0.01058
AFIX  43
H3    2    0.687148    0.338869    0.496693    11.00000   -1.20000
AFIX   0
C9    1    0.500629    0.603770    0.495180    11.00000    0.03871    0.05160 =
         0.04218    0.00018    0.00894    0.00212
AFIX  43
H9    2    0.466515    0.679095    0.546537    11.00000   -1.20000
AFIX   0
C1    1    0.856050    0.410942    0.378756    11.00000    0.04084    0.06094 =
         0.04267   -0.00349    0.00138    0.00834
C2    1    0.786004    0.309105    0.400768    11.00000    0.04835    0.04294 =
         0.06662   -0.00587    0.00271    0.00080
AFIX  43
H2    2    0.773589    0.174707    0.361714    11.00000   -1.20000
AFIX   0
C5    1    0.822572    0.706886    0.514642    11.00000    0.04729    0.04460 =
         0.05407   -0.00450    0.00277   -0.00906
AFIX  43
H5    2    0.835232    0.841536    0.553028    11.00000   -1.20000
AFIX   0
C6    1    0.874686    0.610696    0.434888    11.00000    0.03855    0.06422 =
         0.05401   -0.00076    0.00692   -0.01183
AFIX  43
H6    2    0.921924    0.679363    0.418945    11.00000   -1.20000
AFIX   0
C7    1    0.695112    0.714187    0.628281    11.00000    0.04650    0.06361 =
         0.04944   -0.00671    0.00656   -0.00276
AFIX  23
H7A   2    0.728112    0.787512    0.711612    11.00000   -1.20000
H7B   2    0.663898    0.606015    0.668507    11.00000   -1.20000
AFIX   0
C8    1    0.552008    0.727821    0.409089    11.00000    0.04708    0.05409 =
         0.05215    0.01037    0.01018    0.00386
AFIX  23
H8A   2    0.516436    0.812284    0.335339    11.00000   -1.20000
H8B   2    0.581978    0.630897    0.356563    11.00000   -1.20000
AFIX   0
HKLF 4




REM  fastscan_autored_a.res in P2(1)/c
REM wR2 = 0.0800, GooF = S = 1.029, Restrained GooF = 1.029 for all data
REM R1 = 0.0350 for 1285 Fo > 4sig(Fo) and 0.0525 for all 1641 data
REM 100 parameters refined using 0 restraints

END

WGHT      0.0269      0.4947

REM Highest difference peak  0.401,  deepest hole -0.476,  1-sigma level  0.051
Q1    1   0.9452  0.3871  0.3164  11.00000  0.05    0.40
Q2    1   0.9394  0.1698  0.3374  11.00000  0.05    0.27
Q3    1   0.9050  0.2790  0.2387  11.00000  0.05    0.22
Q4    1   0.8984  0.0596  0.1908  11.00000  0.05    0.18
Q5    1   0.5830  0.8213  0.4584  11.00000  0.05    0.18
;
_shelx_res_checksum              18095
_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 1.167
_oxdiff_exptl_absorpt_empirical_full_min 0.888
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and petroleum ether'
