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_2312777
_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          'C13 H12 O5'
_chemical_formula_moiety         'C13 H12 O5'
_chemical_formula_sum            'C13 H12 O5'
_chemical_formula_weight         248.23
_chemical_name_systematic
;
Ethyl 8-methoxy-2-oxo-2<i>H</i>-1-benzopyran-3-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 100.253(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8708(3)
_cell_length_b                   10.6766(5)
_cell_length_c                   15.7872(8)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.62
_cell_volume                     1139.60(9)
_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_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20764
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         2.622
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9494
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rods
_exptl_crystal_F_000             520
_exptl_crystal_size_max          1.173
_exptl_crystal_size_mid          0.831
_exptl_crystal_size_min          0.512
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.209
_refine_ls_extinction_coef       0.079(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2019 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0477P)^2^+0.3290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2493
_reflns_number_total             2822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ef3062.cif
_cod_data_source_block           S1b
_cod_depositor_comments
'Adding full bibliography for 2312774--2312779.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2312777
_shelx_estimated_absorpt_t_min   0.880
_shelx_estimated_absorpt_t_max   0.945
_shelx_hkl_checksum              33889
_shelx_res_checksum              94245