#------------------------------------------------------------------------------
#$Date: 2022-09-06 04:19:54 +0300 (Tue, 06 Sep 2022) $
#$Revision: 277646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/54/7245444.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_7245444
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         'C9 H9 Br S'
_chemical_formula_sum            'C9 H9 Br S'
_chemical_formula_weight         229.13
_chemical_melting_point          358.0(10)
_chemical_name_systematic        (E)-1,4-bis((4-bromobenzyl)thio)but-2-ene
_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             2021-06-30
_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                 100.622(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5752(12)
_cell_length_b                   6.3230(6)
_cell_length_c                   9.1422(8)
_cell_measurement_reflns_used    1344
_cell_measurement_temperature    304.00(10)
_cell_measurement_theta_max      24.5240
_cell_measurement_theta_min      3.7400
_cell_volume                     941.73(14)
_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      air
_diffrn_ambient_temperature      304.00(10)
_diffrn_detector                 'CCD plate'
_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_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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_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_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_description       block
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and petroleum ether'
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.051
_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_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0350
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1285
_reflns_number_total             1641
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra04872h2.cif
_cod_data_source_block           fastscan_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '357-359' was changed to
'358.0(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               7245444
_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   0.487
_shelx_estimated_absorpt_t_min   0.371
_reflns_odcompleteness_completeness 83.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.66
_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)
;
_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
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
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)
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
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) . . ?
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) . ?
