Copper-Catalyzed Multicomponent Reaction of DABCO·(SO<sub>2</sub>)<sub>2</sub>, Alcohols, and Aryl Diazoniums for the Synthesis of Sulfonic Esters.
Wang, Yang; Deng, Lingling; Deng, Yu; Han, Jianlin; The Journal of organic chemistry 83 (2018) 4674–4680; doi:10.1021/acs.joc.8b00447

data_4034909
_publ_section_title
;
 Copper-Catalyzed Multicomponent Reaction of
 DABCO&#x00B7;(SO<sub>2</sub>)<sub>2</sub>, Alcohols, and Aryl Diazoniums
 for the Synthesis of Sulfonic Esters.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4674
_journal_page_last               4680
_journal_paper_doi               10.1021/acs.joc.8b00447
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C22 H22 O3 S'
_chemical_formula_weight         366.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 109.862(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.352(3)
_cell_length_b                   9.221(3)
_cell_length_c                   11.844(3)
_cell_measurement_reflns_used    3217
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.41
_cell_volume                     960.6(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4774
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         1.828
_exptl_absorpt_coefficient_mu    0.187
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description
;
;
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.1286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.784
_reflns_Friedel_fraction_max     0.784
_reflns_number_gt                2809
_reflns_number_total             2992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00447_si_002.cif
_cod_data_source_block           20171201panyi_TZ_1_0m_a
_cod_original_cell_volume        960.6(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034909
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              86892
_shelx_hkl_checksum              18086