TFA-promoted sulfonation/cascade cyclization of 2-propynolphenols with sodium sulfinates to 4-sulfonyl 2H-chromenes under metal-free conditions
Yang, Tao; Kou, Peihao; Jin, Fengyan; Song, Xian-Rong; Bai, Jiang; Ding, Haixin; Xiao, Qiang; Liang, Yong-Min; Organic Chemistry Frontiers 6 (2019) 3162–; doi:10.1039/C9QO00712A

data_1555027
_publ_section_title
;
 TFA-promoted sulfonation/cascade cyclization of 2-propynolphenols with
 sodium sulfinates to 4-sulfonyl 2H-chromenes under metal-free conditions
;
_journal_issue                   17
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3162
_journal_paper_doi               10.1039/C9QO00712A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C28 H22 O3 S'
_chemical_formula_weight         438.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-12-04 deposited with the CCDC.	2019-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.834(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.465(2)
_cell_length_b                   9.797(2)
_cell_length_c                   22.032(5)
_cell_measurement_reflns_used    8985
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.28
_cell_volume                     2247.1(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17383
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.577
_diffrn_reflns_theta_min         2.789
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0193(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0493P)^2^+1.1300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4168
_reflns_number_total             4989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00712a3.cif
_cod_data_source_block           1
_cod_original_cell_volume        2247.2(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555027
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              2701
_shelx_hkl_checksum              77137