A Radical-Radical Cross-Coupling Reaction of Xanthene with Sulfonyl Hydrazides: Facile Access to Xanthen-9-sulfone Derivatives
Das, Sumit; Roy, Shantonu; Bhowmik, arup; Sarkar, Writhabrata; Mondal, Imtiaj; Mishra, Aniket; Saha, Shubhra Jyoti; Karmakar, Sudip; Deb, Indubhusan; Chemical Communications  (2022) –; doi:10.1039/D1CC07143B

data_7129645
_publ_section_title
;
 A Radical-Radical Cross-Coupling Reaction of Xanthene with Sulfonyl
 Hydrazides: Facile Access to Xanthen-9-sulfone Derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07143B
_journal_year                    2022
_chemical_formula_moiety         'C20 H16 O3 S'
_chemical_formula_sum            'C20 H16 O3 S'
_chemical_formula_weight         336.39
_chemical_name_systematic        9-tosyl-9H-xanthene
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-10-28 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.906(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7563(10)
_cell_length_b                   5.3376(7)
_cell_length_c                   33.444(6)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.43
_cell_measurement_theta_min      2.65
_cell_volume                     1557.4(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            21860
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.530
_diffrn_reflns_theta_max         66.530
_diffrn_reflns_theta_min         2.652
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.975
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1088 before and 0.0638 after correction. The Ratio of minimum to maximum transmission is 0.6590. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pet ether-chloroform'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0695P)^2^+0.7790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2667
_reflns_number_total             2690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc07143b2.cif
_cod_data_source_block           sd_47_0m_a
_cod_original_cell_volume        1557.3(4)
_cod_database_code               7129645
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.693
_shelx_estimated_absorpt_t_min   0.438
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C3(H3), C9(H9), C10(H10), C6(H6), C11(H11), C15(H15),
 C4(H4), C5(H5), C16(H16), C12(H12)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              72982
_shelx_hkl_checksum              39984
_olex2_submission_special_instructions 'No special instructions were received'