Visible-light mediated 3-component synthesis of sulfonylated coumarins from sulfur dioxide
Chen, Zhengkai; Liu, Nai-Wei; Bolte, Michael; Ren, Hongjun; Manolikakes, Georg; Green Chemistry 20 (2018) 3059–; doi:10.1039/C8GC00838H

data_7230821
_publ_section_title
;
 Visible-light mediated 3-component synthesis of sulfonylated coumarins
 from sulfur dioxide
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              3059
_journal_paper_doi               10.1039/C8GC00838H
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C21 H13 Cl O4 S'
_chemical_formula_sum            'C21 H13 Cl O4 S'
_chemical_formula_weight         396.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-04 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.804(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8859(12)
_cell_length_b                   5.6317(3)
_cell_length_c                   25.025(2)
_cell_measurement_reflns_used    19801
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.87
_cell_measurement_theta_min      2.21
_cell_volume                     1813.9(2)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17139
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.517
_diffrn_reflns_theta_min         2.215
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   -0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6690
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0708
_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^)+(0.1460P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1858
_refine_ls_wR_factor_ref         0.1986
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                5144
_reflns_number_total             6690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc00838h2.cif
_cod_data_source_block           ma109
_cod_depositor_comments
'Adding full bibliography for 7230820--7230821.cif.'
_cod_database_code               7230821
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              37481