Copper(II)-Catalyzed Four-Component Oxysulfonylation/Diazenylation: Synthesis of α-Arylhydrazo-β-keto Sulfones.
Gao, Wen-Chao; Cheng, Yu-Fei; Shang, Yu-Zhu; Chang, Hong-Hong; Li, Xing; Zhou, Rong; Qiao, Yan; Wei, Wen-Long; The Journal of organic chemistry 83 (2018) 11956–11962; doi:10.1021/acs.joc.8b01843

data_4035213
_publ_section_title
;
 Copper(II)-Catalyzed Four-Component Oxysulfonylation/Diazenylation:
 Synthesis of \a-Arylhydrazo-\b-keto Sulfones.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11956
_journal_page_last               11962
_journal_paper_doi               10.1021/acs.joc.8b01843
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H19 Cl N2 O4 S'
_chemical_formula_sum            'C22 H19 Cl N2 O4 S'
_chemical_formula_weight         442.90
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
????
;
_cell_angle_alpha                98.357(7)
_cell_angle_beta                 106.844(2)
_cell_angle_gamma                104.871(9)
_cell_formula_units_Z            2
_cell_length_a                   7.934(3)
_cell_length_b                   11.694(5)
_cell_length_c                   12.083(4)
_cell_measurement_reflns_used    3150
_cell_measurement_temperature    153
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1007.4(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      153
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10942
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_min         3.083
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB(Rigaku, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       prism
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0680P)^2^+0.0787P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3776
_reflns_number_total             4453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01843_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1007.4(6)
_cod_database_code               4035213
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.932
_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:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              39250
_shelx_hkl_checksum              26488
_olex2_submission_special_instructions 'No special instructions were received'