#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:29:49 +0300 (Thu, 05 May 2022) $
#$Revision: 274971 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/44/7244421.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_7244421
loop_
_publ_author_name
'Arakawa, Yuki'
'Ishida, Yuko'
'Shiba, Takuma'
'Igawa, Kazunobu'
'Sasaki, Shunsuke'
'Tsuji, Hideto'
_publ_section_title
;
 Effects of alkylthio groups on phase transitions of organic molecules and
 liquid crystals: a comparative study with alkyl and alkoxy groups
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1877
_journal_page_last               1890
_journal_paper_doi               10.1039/D1CE01470F
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C15 H11 N O2 S'
_chemical_formula_sum            'C15 H11 N O2 S'
_chemical_formula_weight         269.32
_chemical_name_systematic        '4-cyanophenyl 4-(methylthio)benzoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-04-24 deposited with the CCDC.	2022-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                106.416(14)
_cell_angle_beta                 91.946(13)
_cell_angle_gamma                91.011(10)
_cell_formula_units_Z            2
_cell_length_a                   6.728(3)
_cell_length_b                   9.172(5)
_cell_length_c                   10.765(6)
_cell_measurement_reflns_used    2808
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.36
_cell_measurement_theta_min      1.97
_cell_volume                     636.6(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10603
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.444
_diffrn_reflns_theta_min         3.031
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280.00
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.72
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0631P)²+0.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2705
_reflns_number_total             2874
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d1ce01470f2.cif
_cod_data_source_block           arakawa-YI3-1(2nd)-FRE
_cod_depositor_comments
'Adding full bibliography for 7244421--7244423.cif.'
_cod_database_code               7244421
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-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 -0.25072(6) 0.17710(5) 0.30738(4) 0.02340(16) Uani 1 1 d . . . . .
O1 O 0.59629(18) 0.45470(14) 0.11660(12) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.54085(17) 0.22361(14) -0.03107(11) 0.0214(3) Uani 1 1 d . . . . .
N1 N 1.2566(3) 0.2169(2) -0.45633(16) 0.0341(4) Uani 1 1 d . . . . .
C1 C -0.3371(3) 0.3523(2) 0.41206(17) 0.0258(4) Uani 1 1 d . . . . .
H1A H -0.352733 0.426732 0.362885 0.031 Uiso 1 1 calc R U . . .
H1B H -0.240058 0.391978 0.484295 0.031 Uiso 1 1 calc R U . . .
H1C H -0.465461 0.333524 0.445956 0.031 Uiso 1 1 calc R U . . .
C2 C -0.0272(2) 0.23076(19) 0.25003(15) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.0546(2) 0.37827(19) 0.28524(15) 0.0194(3) Uani 1 1 d . . . . .
H3 H -0.008745 0.457227 0.346651 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2290(2) 0.40993(19) 0.23051(15) 0.0188(3) Uani 1 1 d . . . . .
H4 H 0.285282 0.510182 0.255894 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3216(2) 0.29525(19) 0.13851(15) 0.0174(3) Uani 1 1 d . . . . .
C6 C 0.2408(2) 0.14674(19) 0.10426(16) 0.0196(3) Uani 1 1 d . . . . .
H6 H 0.303787 0.067843 0.042600 0.024 Uiso 1 1 calc R U . . .
C7 C 0.0693(2) 0.11497(19) 0.16021(16) 0.0198(3) Uani 1 1 d . . . . .
H7 H 0.016224 0.013801 0.137614 0.024 Uiso 1 1 calc R U . . .
C8 C 0.5012(2) 0.33702(19) 0.07865(15) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.6942(2) 0.23588(19) -0.11224(15) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.8804(2) 0.30162(19) -0.06803(16) 0.0192(3) Uani 1 1 d . . . . .
H10 H 0.907973 0.349237 0.021581 0.023 Uiso 1 1 calc R U . . .
C11 C 1.0256(2) 0.29604(19) -0.15822(16) 0.0195(3) Uani 1 1 d . . . . .
H11 H 1.153753 0.340831 -0.130354 0.023 Uiso 1 1 calc R U . . .
C12 C 0.9833(3) 0.22455(19) -0.28997(16) 0.0203(4) Uani 1 1 d . . . . .
C13 C 0.7950(3) 0.1585(2) -0.33266(16) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.767023 0.109754 -0.422048 0.026 Uiso 1 1 calc R U . . .
C14 C 0.6497(3) 0.16483(19) -0.24313(16) 0.0207(3) Uani 1 1 d . . . . .
H14 H 0.520864 0.121176 -0.270702 0.025 Uiso 1 1 calc R U . . .
C15 C 1.1354(3) 0.2197(2) -0.38263(17) 0.0247(4) Uani 1 1 d . . . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(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
C2 S1 C1 103.92(9) . . ?
C8 O2 C9 122.78(13) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 119.29(15) . . ?
C3 C2 S1 124.63(13) . . ?
C7 C2 S1 116.06(13) . . ?
C4 C3 C2 120.10(15) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.45(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.44(15) . . ?
C4 C5 C8 118.13(15) . . ?
C6 C5 C8 122.42(15) . . ?
C7 C6 C5 120.03(15) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.65(16) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
O1 C8 O2 124.03(15) . . ?
O1 C8 C5 125.86(15) . . ?
O2 C8 C5 110.07(14) . . ?
C10 C9 C14 122.06(15) . . ?
C10 C9 O2 123.98(15) . . ?
C14 C9 O2 113.77(15) . . ?
C9 C10 C11 118.39(15) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C10 C11 C12 120.20(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.61(15) . . ?
C13 C12 C15 119.78(16) . . ?
C11 C12 C15 119.62(16) . . ?
C14 C13 C12 119.30(15) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 119.44(16) . . ?
C13 C14 H14 120.3 . . ?
C9 C14 H14 120.3 . . ?
N1 C15 C12 179.5(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
S1 C2 1.7586(18) . ?
S1 C1 1.801(2) . ?
O1 C8 1.204(2) . ?
O2 C8 1.373(2) . ?
O2 C9 1.3975(19) . ?
N1 C15 1.152(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.395(2) . ?
C2 C7 1.404(2) . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(2) . ?
C5 C8 1.482(2) . ?
C6 C7 1.383(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.389(2) . ?
C9 C14 1.395(2) . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.400(2) . ?
C12 C15 1.446(2) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 H14 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
C1 S1 C2 C3 1.06(17) . . . . ?
C1 S1 C2 C7 -177.30(12) . . . . ?
C7 C2 C3 C4 0.7(2) . . . . ?
S1 C2 C3 C4 -177.64(12) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C3 C4 C5 C6 -1.8(2) . . . . ?
C3 C4 C5 C8 176.99(14) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C8 C5 C6 C7 -177.94(15) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C3 C2 C7 C6 -1.7(2) . . . . ?
S1 C2 C7 C6 176.77(13) . . . . ?
C9 O2 C8 O1 -1.8(2) . . . . ?
C9 O2 C8 C5 175.84(13) . . . . ?
C4 C5 C8 O1 13.5(3) . . . . ?
C6 C5 C8 O1 -167.71(17) . . . . ?
C4 C5 C8 O2 -164.09(14) . . . . ?
C6 C5 C8 O2 14.7(2) . . . . ?
C8 O2 C9 C10 39.6(2) . . . . ?
C8 O2 C9 C14 -145.26(15) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
O2 C9 C10 C11 174.95(14) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C10 C11 C12 C15 179.93(15) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C15 C12 C13 C14 -179.47(16) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C10 C9 C14 C13 0.3(3) . . . . ?
O2 C9 C14 C13 -174.99(15) . . . . ?
