#------------------------------------------------------------------------------
#$Date: 2022-09-06 03:19:54 +0200 (Tue 06 de Sep de 2022) $
#$Revision: 277646 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/54/7245443.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245443
loop_
_publ_author_name
'Kotha, Sambasivarao'
'Gupta, Naveen Kumar'
'Ansari, Saima'
_publ_section_title
;
 One-pot thiol-free synthetic approach to sulfides, and sulfoxides
 selectively
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              25154
_journal_page_last               25162
_journal_paper_doi               10.1039/D2RA04872H
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C8 H8 Br S'
_chemical_formula_sum            'C8 H8 Br S'
_chemical_formula_weight         216.11
_chemical_melting_point          368.0(10)
_chemical_name_systematic        1,2-bis(4-bromobenzyl)thio)ethane
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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)
;
_audit_update_record
;
2022-04-21 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.329(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6134(6)
_cell_length_b                   5.5697(2)
_cell_length_c                   9.1693(4)
_cell_measurement_reflns_used    2004
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.0400
_cell_measurement_theta_min      2.5220
_cell_volume                     822.06(6)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_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_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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and petroleum ether'
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.066
_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_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0264
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1203
_reflns_number_total             1385
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra04872h2.cif
_cod_data_source_block           srk_sp_2_21_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '367-369' was changed to
'368.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7245443
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.566
_shelx_estimated_absorpt_t_min   0.217
_reflns_odcompleteness_completeness 75.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.71
_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)
;
_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
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'
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)
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'
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) . . ?
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) . ?
