#------------------------------------------------------------------------------
#$Date: 2023-08-05 11:35:47 +0200 (Sat 05 de Aug de 2023) $
#$Revision: 285529 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/69/7246962.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_7246962
loop_
_publ_author_name
'Mandal, Koushik'
'Hasija, Avantika'
'Shukla, Rahul'
'Hathwar, Venkatesha R.'
'Chopra, Deepak'
_publ_section_title
;
 Quantitative evaluation of the electronic features involving
 "nucleophilic-electrophilic" character in the chalcogen sulfur.
;
_journal_issue                   29
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              19427
_journal_page_last               19434
_journal_paper_doi               10.1039/d3cp02526h
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C5 H4 O S'
_chemical_formula_sum            'C5 H4 O S'
_chemical_formula_weight         112.14
_chemical_name_systematic        1A
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-31 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.52550(10)
_cell_length_b                   5.90890(10)
_cell_length_c                   16.0342(4)
_cell_measurement_reflns_used    4892
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.77
_cell_measurement_theta_min      2.55
_cell_volume                     523.511(18)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.873
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.873
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7298
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.686
_diffrn_reflns_theta_min         2.541
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0711 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8713.
The λ/2 correction factor is Not present.
;
_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    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_recrystallization_method 'Insitu cryocrystallization'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 365 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0311
_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)+(0.0513P)²+0.1160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                949
_reflns_number_total             966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp02526h2.cif
_cod_data_source_block           1A
_cod_depositor_comments
'Adding full bibliography for 7246960--7246964.cif.'
_cod_database_code               7246962
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
;
_shelx_res_file
;
TITL ORTHO1_a.res in P2(1)2(1)2(1)
    2cht.res
    created by SHELXL-2018/3 at 05:20:51 on 22-May-2023
REM Old TITL ORTHO1 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.119, Rweak 0.041, Alpha 0.001, Orientation as input
REM Flack x = 0.079 ( 0.031 ) from Parsons' quotients
REM Formula found by SHELXT: C5 O S
CELL 0.71073 5.5255 5.9089 16.0342 90 90 90
ZERR 4 0.0001 0.0001 0.0004 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H O S
UNIT 20 16 4 4

L.S. 10
PLAN  1
TEMP -173.15
CONF
BOND $H
LIST 4
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\2CHT.hkl">
REM </olex2.extras>

WGHT    0.051300    0.116000
FVAR       1.85101
S1    4    0.487068    0.613871    0.557298    11.00000    0.05431    0.04163 =
         0.05664    0.00907    0.01056    0.00140
O1    3    0.063225    0.814433    0.654137    11.00000    0.06518    0.06041 =
         0.06284   -0.01086   -0.00746    0.02456
C2    1    0.425355    0.300440    0.667017    11.00000    0.05015    0.03647 =
         0.04760    0.00093   -0.00731    0.00179
AFIX  43
H2    2    0.362955    0.213867    0.712074    11.00000   -1.20000
AFIX   0
C5    1    0.131719    0.630375    0.677038    11.00000    0.04904    0.05857 =
         0.04159   -0.00441   -0.00103    0.00355
AFIX  43
H5    2    0.047236    0.561036    0.721869    11.00000   -1.20000
AFIX   0
C1    1    0.333027    0.508131    0.641096    11.00000    0.03829    0.03484 =
         0.03671   -0.00054   -0.00377   -0.00176
C3    1    0.624942    0.235999    0.617022    11.00000    0.05284    0.03546 =
         0.06675   -0.00638   -0.01958    0.00961
AFIX  43
H3    2    0.713900    0.100203    0.625162    11.00000   -1.20000
AFIX   0
C4    1    0.675872    0.388584    0.556238    11.00000    0.03826    0.04994 =
         0.06842   -0.01192    0.00500    0.00392
AFIX  43
H4    2    0.803920    0.370751    0.517250    11.00000   -1.20000
AFIX   0
HKLF 4




REM  ORTHO1_a.res in P2(1)2(1)2(1)
REM wR2 = 0.0886, GooF = S = 1.112, Restrained GooF = 1.112 for all data
REM R1 = 0.0311 for 949 Fo > 4sig(Fo) and 0.0315 for all 966 data
REM 64 parameters refined using 0 restraints

END

WGHT      0.0513      0.1160

REM Highest difference peak  0.185,  deepest hole -0.258,  1-sigma level  0.039
Q1    1   0.5829  0.4974  0.5619  11.00000  0.05    0.19
;
_shelx_res_checksum              11763
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
S1 S 0.48707(17) 0.61387(11) 0.55730(4) 0.0509(3) Uani 1 1 d . . . . .
O1 O 0.0632(5) 0.8144(4) 0.65414(14) 0.0628(8) Uani 1 1 d . . . . .
C2 C 0.4254(6) 0.3004(4) 0.66702(17) 0.0447(8) Uani 1 1 d . . . . .
H2 H 0.362955 0.213867 0.712074 0.054 Uiso 1 1 calc R U . . .
C5 C 0.1317(7) 0.6304(5) 0.67704(17) 0.0497(8) Uani 1 1 d . . . . .
H5 H 0.047236 0.561036 0.721869 0.060 Uiso 1 1 calc R U . . .
C1 C 0.3330(6) 0.5081(4) 0.64110(15) 0.0366(6) Uani 1 1 d . . . . .
C3 C 0.6249(7) 0.2360(5) 0.6170(2) 0.0517(8) Uani 1 1 d . . . . .
H3 H 0.713900 0.100203 0.625162 0.062 Uiso 1 1 calc R U . . .
C4 C 0.6759(6) 0.3886(5) 0.5562(2) 0.0522(8) Uani 1 1 d . . . . .
H4 H 0.803920 0.370751 0.517250 0.063 Uiso 1 1 calc R U . . .
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
S1 0.0543(6) 0.0416(4) 0.0566(4) 0.0091(3) 0.0106(4) 0.0014(4)
O1 0.065(2) 0.0604(13) 0.0628(12) -0.0109(10) -0.0075(12) 0.0246(12)
C2 0.050(2) 0.0365(12) 0.0476(13) 0.0009(11) -0.0073(12) 0.0018(11)
C5 0.049(2) 0.0586(17) 0.0416(12) -0.0044(13) -0.0010(13) 0.0035(15)
C1 0.0383(19) 0.0348(12) 0.0367(11) -0.0005(9) -0.0038(11) -0.0018(11)
C3 0.053(2) 0.0355(13) 0.0668(17) -0.0064(13) -0.0196(16) 0.0096(13)
C4 0.038(2) 0.0499(16) 0.0684(18) -0.0119(16) 0.0050(15) 0.0039(12)
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'
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'
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
C4 S1 C1 91.57(15) . . ?
C1 C2 H2 124.7 . . ?
C1 C2 C3 110.7(3) . . ?
C3 C2 H2 124.7 . . ?
O1 C5 H5 117.7 . . ?
O1 C5 C1 124.7(3) . . ?
C1 C5 H5 117.7 . . ?
C2 C1 S1 112.0(2) . . ?
C2 C1 C5 127.1(3) . . ?
C5 C1 S1 120.9(2) . . ?
C2 C3 H3 123.5 . . ?
C4 C3 C2 112.9(3) . . ?
C4 C3 H3 123.5 . . ?
S1 C4 H4 123.6 . . ?
C3 C4 S1 112.8(3) . . ?
C3 C4 H4 123.6 . . ?
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
S1 C1 1.709(3) . ?
S1 C4 1.691(3) . ?
O1 C5 1.209(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.393(4) . ?
C2 C3 1.416(5) . ?
C5 H5 0.9500 . ?
C5 C1 1.446(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.357(5) . ?
C4 H4 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C1 S1 -2.9(5) . . . . ?
O1 C5 C1 C2 177.3(3) . . . . ?
C2 C3 C4 S1 0.2(4) . . . . ?
C1 S1 C4 C3 0.3(3) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C3 C2 C1 S1 0.9(3) . . . . ?
C3 C2 C1 C5 -179.3(3) . . . . ?
C4 S1 C1 C2 -0.7(2) . . . . ?
C4 S1 C1 C5 179.5(3) . . . . ?
