Metal-free annulative hydrosulfonation of propiolate esters: synthesis of 4-sulfonates of coumarins and butenolides
Fernandes, Rodney A.; Gangani, Ashvin J.; Kunkalkar, Rupesh A.; New Journal of Chemistry 44 (2020) 3970–3984; doi:10.1039/C9NJ06438A

data_7059321
_publ_section_title
;
 Metal-free annulative hydrosulfonation of propiolate esters: synthesis of
 4-sulfonates of coumarins and butenolides
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3970
_journal_page_last               3984
_journal_paper_doi               10.1039/C9NJ06438A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C17 H14 O5 S'
_chemical_formula_sum            'C17 H14 O5 S'
_chemical_formula_weight         330.35
_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
_audit_creation_date             2019-07-19
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-07-23 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.300(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5139(6)
_cell_length_b                   11.8830(8)
_cell_length_c                   13.6051(9)
_cell_measurement_reflns_used    2749
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.2300
_cell_measurement_theta_min      2.3620
_cell_volume                     1496.85(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -79.00  70.00   1.00    8.00    --  -20.00   0.00  36.00  149
  2  \w    -93.00 -72.00   1.00    8.00    --  -20.00 -72.00-108.00   21
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684862000
_diffrn_orient_matrix_UB_12      -0.0230637000
_diffrn_orient_matrix_UB_13      -0.0228403000
_diffrn_orient_matrix_UB_21      0.0085045000
_diffrn_orient_matrix_UB_22      0.0178791000
_diffrn_orient_matrix_UB_23      -0.0480296000
_diffrn_orient_matrix_UB_31      0.0332468000
_diffrn_orient_matrix_UB_32      -0.0520702000
_diffrn_orient_matrix_UB_33      -0.0064219000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4668
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.303
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.7441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1986
_reflns_number_total             2559
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj06438a2.cif
_cod_data_source_block           raf-rku-2-061-pc-ptsa_mo
_cod_depositor_comments
;

 Adding full bibliography for 7059321.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11.33 H9.33 O3.33 S0.67'
_cod_original_formula_weight         220.23
_cod_original_formula_moiety         '0.67(C17 H14 O5 S)'
_cod_original_formula_units_Z            6
_cod_original_cell_volume        1496.86(18)
_cod_database_code               7059321
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 82.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.09
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00D), C00B(H00E), C00E(H00I), C00F(H00J), C00G(H00K), C00K(H00L),
 C00L(H00M), C00M(H00N)
2.b Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C), C00C(H00F,H00G,H00H)
;
_shelx_res_checksum              53734
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.757