#------------------------------------------------------------------------------
#$Date: 2023-04-05 19:02:36 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282420 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312059.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312059
loop_
_publ_author_name
'Sample, Harry C.'
'Twamley, Brendan'
'Senge, Mathias O.'
_publ_section_title
;
 Structures of S-(pyridin-2-yl) 4-nitro-benzo-thio-ate,
 S-(pyridin-2-yl) 4-methyl-benzo-thio-ate and
 S-(pyridin-2-yl) 4-meth-oxy-benzo-thio-ate: building blocks for
 low-symmetry multifunctional tetra-pyrroles.
;
_journal_coeditor_code           YZ2028
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              157
_journal_page_last               162
_journal_paper_doi               10.1107/S2056989023001056
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C13 H11 N O S'
_chemical_formula_moiety         'C13 H11 N O S'
_chemical_formula_sum            'C13 H11 N O S'
_chemical_formula_weight         229.29
_chemical_name_systematic
;
S-(Pyridin-2-yl) 4-methylbenzothioate
;
_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     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                101.2966(14)
_cell_angle_beta                 108.4632(13)
_cell_angle_gamma                92.5673(14)
_cell_formula_units_Z            2
_cell_length_a                   7.1775(2)
_cell_length_b                   9.1492(3)
_cell_length_c                   9.2832(3)
_cell_measurement_reflns_used    5814
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.05
_cell_measurement_theta_min      4.962
_cell_volume                     563.28(3)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII Kappa Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7937
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.044
_diffrn_reflns_theta_min         4.962
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.59
_diffrn_source_power             0.29275800000000E-1
_diffrn_source_voltage           49.62
_exptl_absorpt_coefficient_mu    2.352
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0419
_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)+(0.0776P)²+0.2152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1260
_reflns_number_gt                1958
_reflns_number_total             2106
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2028sup1.cif
_cod_data_source_block           2
_cod_database_code               2312059
_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_min   0.463
_shelx_estimated_absorpt_t_max   0.813
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.49730(6) 0.81629(5) 0.54572(5) 0.02575(19) Uani d 1 . .
N N1 0.1173(2) 0.85006(17) 0.44707(17) 0.0239(3) Uani d 1 . .
C C2 -0.0761(3) 0.8008(2) 0.3793(2) 0.0250(4) Uani d 1 . .
H H2 -0.167830 0.872979 0.368508 0.030 Uiso calc 1 . .
C C3 -0.1488(3) 0.6502(2) 0.3242(2) 0.0245(4) Uani d 1 . .
H H3 -0.286999 0.620400 0.278163 0.029 Uiso calc 1 . .
C C4 -0.0162(3) 0.5439(2) 0.3376(2) 0.0241(4) Uani d 1 . .
H H4 -0.061528 0.439922 0.300499 0.029 Uiso calc 1 . .
C C5 0.1838(3) 0.5928(2) 0.4062(2) 0.0237(4) Uani d 1 . .
H H5 0.279047 0.523231 0.416127 0.028 Uiso calc 1 . .
C C6 0.2416(3) 0.7455(2) 0.4599(2) 0.0219(4) Uani d 1 . .
C C8 0.5659(3) 0.73280(19) 0.7124(2) 0.0216(4) Uani d 1 . .
O O9 0.44856(19) 0.65460(16) 0.74143(15) 0.0294(3) Uani d 1 . .
C C10 0.7791(3) 0.76691(19) 0.8087(2) 0.0218(4) Uani d 1 . .
C C11 0.8476(3) 0.6978(2) 0.9337(2) 0.0241(4) Uani d 1 . .
H H11 0.757864 0.634654 0.957347 0.029 Uiso calc 1 . .
C C12 1.0455(3) 0.7206(2) 1.0234(2) 0.0250(4) Uani d 1 . .
H H12 1.090277 0.672879 1.108358 0.030 Uiso calc 1 . .
C C13 1.1805(3) 0.8126(2) 0.9914(2) 0.0247(4) Uani d 1 . .
C C14 1.1111(3) 0.8823(2) 0.8667(2) 0.0255(4) Uani d 1 . .
H H14 1.201135 0.945560 0.843497 0.031 Uiso calc 1 . .
C C15 0.9125(3) 0.8605(2) 0.7760(2) 0.0229(4) Uani d 1 . .
H H15 0.867412 0.909236 0.691895 0.028 Uiso calc 1 . .
C C16 1.3959(3) 0.8344(2) 1.0883(2) 0.0313(5) Uani d 1 . .
H H16A 1.433901 0.939493 1.144431 0.047 Uiso calc 1 . .
H H16B 1.475338 0.808356 1.020416 0.047 Uiso calc 1 . .
H H16C 1.418740 0.769623 1.163247 0.047 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 2.00 1.00 0.0700
2.00 -2.00 -1.00 0.0930
1.00 0.00 0.00 0.0780
0.00 0.00 1.00 0.0030
0.00 0.00 -1.00 0.0220
1.00 5.00 -1.00 0.0350
-1.00 -6.00 1.00 0.0400
-1.00 -1.00 3.00 0.0360
-3.00 -2.00 1.00 0.0740
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 S1 C8 . . 100.57(8) ?
C6 N1 C2 . . 116.56(16) ?
N1 C2 H2 . . 118.3 ?
N1 C2 C3 . . 123.44(16) ?
C3 C2 H2 . . 118.3 ?
C2 C3 H3 . . 120.6 ?
C4 C3 C2 . . 118.82(16) ?
C4 C3 H3 . . 120.6 ?
C3 C4 H4 . . 120.8 ?
C5 C4 C3 . . 118.49(17) ?
C5 C4 H4 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
C6 C5 C4 . . 118.36(16) ?
C6 C5 H5 . . 120.8 ?
N1 C6 S1 . . 114.99(14) ?
N1 C6 C5 . . 124.31(16) ?
C5 C6 S1 . . 120.64(14) ?
O9 C8 S1 . . 122.42(14) ?
O9 C8 C10 . . 123.49(16) ?
C10 C8 S1 . . 114.09(12) ?
C11 C10 C8 . . 117.77(16) ?
C11 C10 C15 . . 119.22(16) ?
C15 C10 C8 . . 122.97(16) ?
C10 C11 H11 . . 119.8 ?
C12 C11 C10 . . 120.32(17) ?
C12 C11 H11 . . 119.8 ?
C11 C12 H12 . . 119.5 ?
C11 C12 C13 . . 121.07(17) ?
C13 C12 H12 . . 119.5 ?
C12 C13 C14 . . 118.44(17) ?
C12 C13 C16 . . 120.50(17) ?
C14 C13 C16 . . 121.06(17) ?
C13 C14 H14 . . 119.5 ?
C15 C14 C13 . . 121.01(17) ?
C15 C14 H14 . . 119.5 ?
C10 C15 H15 . . 120.0 ?
C14 C15 C10 . . 119.94(16) ?
C14 C15 H15 . . 120.0 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 . 1.7853(18) ?
S1 C8 . 1.7981(18) ?
N1 C2 . 1.344(2) ?
N1 C6 . 1.333(2) ?
C2 H2 . 0.9500 ?
C2 C3 . 1.387(3) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.386(3) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.385(3) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.385(3) ?
C8 O9 . 1.208(2) ?
C8 C10 . 1.490(2) ?
C10 C11 . 1.394(3) ?
C10 C15 . 1.398(3) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.383(3) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.394(3) ?
C13 C14 . 1.395(3) ?
C13 C16 . 1.503(2) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.389(2) ?
C15 H15 . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 N1 2_576 0.95 2.70 3.355(2) 126.4 yes
C3 H3 O9 2_566 0.95 2.67 3.278(2) 122.2 yes
C4 H4 O9 2_566 0.95 2.75 3.316(2) 118.7 yes
C16 H16B O9 1_655 0.98 2.64 3.460(2) 141.6 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S1 C8 C10 C11 . . . . -175.48(13) ?
S1 C8 C10 C15 . . . . 2.5(2) ?
N1 C2 C3 C4 . . . . -0.8(3) ?
C2 N1 C6 S1 . . . . 178.32(12) ?
C2 N1 C6 C5 . . . . 1.1(3) ?
C2 C3 C4 C5 . . . . 0.3(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
C4 C5 C6 S1 . . . . -178.64(13) ?
C4 C5 C6 N1 . . . . -1.6(3) ?
C6 S1 C8 O9 . . . . -1.13(17) ?
C6 S1 C8 C10 . . . . 178.01(12) ?
C6 N1 C2 C3 . . . . 0.1(3) ?
C8 S1 C6 N1 . . . . 120.11(14) ?
C8 S1 C6 C5 . . . . -62.55(16) ?
C8 C10 C11 C12 . . . . 177.48(16) ?
C8 C10 C15 C14 . . . . -177.17(16) ?
O9 C8 C10 C11 . . . . 3.7(3) ?
O9 C8 C10 C15 . . . . -178.40(17) ?
C10 C11 C12 C13 . . . . 0.0(3) ?
C11 C10 C15 C14 . . . . 0.7(3) ?
C11 C12 C13 C14 . . . . 0.4(3) ?
C11 C12 C13 C16 . . . . -178.99(17) ?
C12 C13 C14 C15 . . . . -0.2(3) ?
C13 C14 C15 C10 . . . . -0.4(3) ?
C15 C10 C11 C12 . . . . -0.5(3) ?
C16 C13 C14 C15 . . . . 179.19(16) ?

_cod_database_fobs_code 2312059
