Structures of <i>S</i>-(pyridin-2-yl) 4-nitro-benzo-thio-ate, <i>S</i>-(pyridin-2-yl) 4-methyl-benzo-thio-ate and <i>S</i>-(pyridin-2-yl) 4-meth-oxy-benzo-thio-ate: building blocks for low-symmetry multifunctional tetra-pyrroles.
Sample, Harry C.; Twamley, Brendan; Senge, Mathias O.; Acta crystallographica. Section E, Crystallographic communications 79 (2023) 157–162; doi:10.1107/S2056989023001056

data_2312058
_publ_section_title
;
 Structures of <i>S</i>-(pyridin-2-yl) 4-nitro-benzo-thio-ate,
 <i>S</i>-(pyridin-2-yl) 4-methyl-benzo-thio-ate and
 <i>S</i>-(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
;
<i>S</i>-(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 <i>et al.</i>,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (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       '\w and \f 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 <i>et al.</i>,  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 <i>x</i> determined using 584 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  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/[\s^2^(Fo^2^)+(0.0767P)^2^+0.6178P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            yz2028sup1.cif
_cod_data_source_block           1
_cod_database_code               2312058
_shelx_estimated_absorpt_t_min   0.444
_shelx_estimated_absorpt_t_max   0.902
_shelx_hkl_checksum              83487
_shelx_res_checksum              23388
_cod_database_fobs_code 2312058