#------------------------------------------------------------------------------
#$Date: 2023-04-05 19:02:36 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282420 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312058.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_2312058
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_absolute_configuration ad
_chemical_formula_iupac          'C12 H8 N2 O3 S'
_chemical_formula_moiety         'C12 H8 N2 O3 S'
_chemical_formula_sum            'C12 H8 N2 O3 S'
_chemical_formula_weight         260.26
_chemical_name_systematic
;
S-(Pyridin-2-yl) 4-nitrobenzothioate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.0774(11)
_cell_length_b                   12.5622(5)
_cell_length_c                   3.8498(2)
_cell_measurement_reflns_used    5322
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.287
_cell_measurement_theta_min      3.831
_cell_volume                     1116.07(9)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0616
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8764
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.798
_diffrn_reflns_theta_min         3.831
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.029796
_diffrn_source_voltage           49.66
_exptl_absorpt_coefficient_mu    2.621
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.261
_refine_ls_abs_structure_details
;
Flack x determined using 584 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0434
_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)+(0.0767P)²+0.6178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                1759
_reflns_number_total             1870
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2028sup1.cif
_cod_data_source_block           1
_cod_database_code               2312058
_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   0.444
_shelx_estimated_absorpt_t_max   0.902
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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
C C2 0.36818(18) 0.8352(3) 0.5521(14) 0.0304(9) Uani d 1 . .
H H2 0.330987 0.825272 0.451494 0.037 Uiso calc 1 . .
C C3 0.38137(18) 0.9340(3) 0.6888(13) 0.0306(9) Uani d 1 . .
H H3 0.354398 0.990981 0.674849 0.037 Uiso calc 1 . .
C C4 0.43473(19) 0.9481(3) 0.8464(12) 0.0282(9) Uani d 1 . .
H H4 0.444798 1.014804 0.945957 0.034 Uiso calc 1 . .
C C5 0.47344(17) 0.8632(3) 0.8569(12) 0.0259(8) Uani d 1 . .
H H5 0.510275 0.869893 0.964831 0.031 Uiso calc 1 . .
C C6 0.45619(15) 0.7686(3) 0.7039(12) 0.0240(8) Uani d 1 . .
C C8 0.56755(16) 0.7014(3) 0.5347(11) 0.0250(9) Uani d 1 . .
C C10 0.61366(16) 0.6184(3) 0.4955(11) 0.0228(8) Uani d 1 . .
C C11 0.60607(17) 0.5140(3) 0.6121(11) 0.0238(8) Uani d 1 . .
H H11 0.571383 0.494357 0.728517 0.029 Uiso calc 1 . .
C C12 0.64936(16) 0.4390(3) 0.5575(12) 0.0250(8) Uani d 1 . .
H H12 0.644736 0.367567 0.633914 0.030 Uiso calc 1 . .
C C13 0.69883(17) 0.4706(3) 0.3907(12) 0.0249(8) Uani d 1 . .
C C14 0.70817(17) 0.5742(3) 0.2745(11) 0.0251(9) Uani d 1 . .
H H14 0.743200 0.593441 0.161129 0.030 Uiso calc 1 . .
C C15 0.66456(17) 0.6483(3) 0.3299(11) 0.0244(9) Uani d 1 . .
H H15 0.669537 0.719721 0.254326 0.029 Uiso calc 1 . .
N N1 0.40512(14) 0.7521(2) 0.5536(10) 0.0265(7) Uani d 1 . .
N N16 0.74430(14) 0.3901(2) 0.3212(10) 0.0278(8) Uani d 1 . .
O O9 0.57457(12) 0.79289(18) 0.4455(9) 0.0293(7) Uani d 1 . .
O O17 0.73740(13) 0.3009(2) 0.4467(10) 0.0379(8) Uani d 1 . .
O O18 0.78579(13) 0.4153(2) 0.1448(12) 0.0449(10) Uani d 1 . .
S S1 0.50105(4) 0.65266(6) 0.7155(4) 0.0241(3) Uani d 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_
_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
C3 C2 H2 . . 118.1 ?
N1 C2 H2 . . 118.1 ?
N1 C2 C3 . . 123.7(4) ?
C2 C3 H3 . . 120.7 ?
C2 C3 C4 . . 118.5(3) ?
C4 C3 H3 . . 120.7 ?
C3 C4 H4 . . 120.5 ?
C3 C4 C5 . . 119.0(4) ?
C5 C4 H4 . . 120.5 ?
C4 C5 H5 . . 121.3 ?
C6 C5 C4 . . 117.5(4) ?
C6 C5 H5 . . 121.3 ?
C5 C6 S1 . . 121.5(3) ?
N1 C6 C5 . . 125.0(3) ?
N1 C6 S1 . . 113.4(3) ?
C10 C8 S1 . . 114.2(3) ?
O9 C8 C10 . . 122.5(4) ?
O9 C8 S1 . . 123.3(3) ?
C11 C10 C8 . . 122.2(3) ?
C15 C10 C8 . . 117.3(3) ?
C15 C10 C11 . . 120.5(3) ?
C10 C11 H11 . . 120.1 ?
C12 C11 C10 . . 119.9(4) ?
C12 C11 H11 . . 120.1 ?
C11 C12 H12 . . 120.9 ?
C13 C12 C11 . . 118.3(3) ?
C13 C12 H12 . . 120.9 ?
C12 C13 C14 . . 123.4(3) ?
C12 C13 N16 . . 118.5(3) ?
C14 C13 N16 . . 118.0(4) ?
C13 C14 H14 . . 121.1 ?
C15 C14 C13 . . 117.7(4) ?
C15 C14 H14 . . 121.1 ?
C10 C15 H15 . . 119.9 ?
C14 C15 C10 . . 120.2(3) ?
C14 C15 H15 . . 119.9 ?
C6 N1 C2 . . 116.2(3) ?
O17 N16 C13 . . 117.3(3) ?
O18 N16 C13 . . 118.8(3) ?
O18 N16 O17 . . 123.9(3) ?
C6 S1 C8 . . 102.01(17) ?
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
C2 H2 . 0.9500 ?
C2 C3 . 1.382(6) ?
C2 N1 . 1.348(5) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.384(6) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.392(5) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.385(5) ?
C6 N1 . 1.329(5) ?
C6 S1 . 1.787(3) ?
C8 C10 . 1.497(5) ?
C8 O9 . 1.210(4) ?
C8 S1 . 1.793(4) ?
C10 C11 . 1.397(5) ?
C10 C15 . 1.388(6) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.389(5) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.369(6) ?
C13 C14 . 1.393(5) ?
C13 N16 . 1.482(5) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.388(5) ?
C15 H15 . 0.9500 ?
N16 O17 . 1.231(4) ?
N16 O18 . 1.215(5) ?
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
C3 H3 O18 3_466 0.95 2.68 3.396(5) 132.9 yes
C4 H4 O9 2_675 0.95 2.46 3.283(4) 145.3 yes
C5 H5 O9 1_556 0.95 2.56 3.371(5) 143.2 yes
C12 H12 N1 2_665 0.95 2.49 3.315(5) 145.4 yes
C14 H14 O17 4_654 0.95 2.77 3.359(4) 120.9 yes
C15 H15 O17 4_654 0.95 2.66 3.312(5) 126.6 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
C2 C3 C4 C5 . . . . 1.0(7) ?
C3 C2 N1 C6 . . . . 1.5(7) ?
C3 C4 C5 C6 . . . . 0.6(7) ?
C4 C5 C6 N1 . . . . -1.3(7) ?
C4 C5 C6 S1 . . . . -177.6(3) ?
C5 C6 N1 C2 . . . . 0.3(7) ?
C5 C6 S1 C8 . . . . -54.6(4) ?
C8 C10 C11 C12 . . . . 177.5(4) ?
C8 C10 C15 C14 . . . . -177.7(4) ?
C10 C8 S1 C6 . . . . -177.2(3) ?
C10 C11 C12 C13 . . . . 0.4(6) ?
C11 C10 C15 C14 . . . . 0.9(6) ?
C11 C12 C13 C14 . . . . 0.3(6) ?
C11 C12 C13 N16 . . . . -178.0(4) ?
C12 C13 C14 C15 . . . . -0.5(6) ?
C12 C13 N16 O17 . . . . -6.7(6) ?
C12 C13 N16 O18 . . . . 173.1(4) ?
C13 C14 C15 C10 . . . . -0.1(6) ?
C14 C13 N16 O17 . . . . 174.9(4) ?
C14 C13 N16 O18 . . . . -5.3(6) ?
C15 C10 C11 C12 . . . . -1.0(6) ?
N1 C2 C3 C4 . . . . -2.1(8) ?
N1 C6 S1 C8 . . . . 128.6(3) ?
N16 C13 C14 C15 . . . . 177.8(4) ?
O9 C8 C10 C11 . . . . 177.3(4) ?
O9 C8 C10 C15 . . . . -4.1(6) ?
O9 C8 S1 C6 . . . . 1.5(4) ?
S1 C6 N1 C2 . . . . 176.9(3) ?
S1 C8 C10 C11 . . . . -4.0(5) ?
S1 C8 C10 C15 . . . . 174.6(3) ?

_cod_database_fobs_code 2312058
