Synthesis and characterization of coumarin-derived sulfur analogues using Lawesson's reagent.
Mama, Neliswa; Schoeman, Stiaan; Myburgh, Lisa; Hosten, Eric C.; Acta crystallographica. Section C, Structural chemistry 81 (2025) 170–180; doi:10.1107/S2053229625000956

data_2312776
_publ_section_title
;
 Synthesis and characterization of coumarin-derived sulfur analogues using
 Lawesson's reagent.
;
_journal_coeditor_code           EF3062
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              170
_journal_page_last               180
_journal_paper_doi               10.1107/S2053229625000956
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C12 H10 O2 S2'
_chemical_formula_moiety         'C12 H10 O2 S2'
_chemical_formula_sum            'C12 H10 O2 S2'
_chemical_formula_weight         250.32
_chemical_name_systematic
;
Ethyl 2-sulfanylidene-2<i>H</i>-chromene-3-carbothioate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
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_atom_sites_solution_hydrogens   geom
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_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5314(5)
_cell_length_b                   6.7175(3)
_cell_length_c                   27.7746(10)
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_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.94
_cell_volume                     2335.38(16)
_computing_cell_refinement
;
APEX2 (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020) and Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b) and ShelXle (H\"ubschle <i>et al.</i>,
2011)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'Bruker PHOTON II CCD 7 detector'
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_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_limit_h_max       16
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_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            27927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         2.937
_diffrn_source                   'sealed x-ray tube'
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_diffrn_source_power             70
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.436
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_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.287
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0401
_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/[\s^2^(Fo^2^)+(0.0316P)^2^+3.2817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                2326
_reflns_number_total             2894
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_depositor_comments
'Adding full bibliography for 2312774--2312779.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2312776
_shelx_estimated_absorpt_t_min   0.880
_shelx_estimated_absorpt_t_max   0.956
_shelx_hkl_checksum              45188
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