Three-Component Coupling Reactions of Aryne, DMSO, and Activated Alkyne: Stereoselective Synthesis of 2-[( o-Methylthio)aryloxy]-Substituted Dialkyl Maleates.
Hazarika, Hemanta; Neog, Kashmiri; Sharma, Abhilash; Das, Babulal; Gogoi, Pranjal; The Journal of organic chemistry 84 (2019) 5846–5854; doi:10.1021/acs.joc.9b00090

data_4034337
_publ_section_title
;
 Three-Component Coupling Reactions of Aryne, DMSO, and Activated Alkyne:
 Stereoselective Synthesis of 2-[( o-Methylthio)aryloxy]-Substituted
 Dialkyl Maleates.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5846
_journal_page_last               5854
_journal_paper_doi               10.1021/acs.joc.9b00090
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C19 H26 O5 S'
_chemical_formula_weight         366.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1461(3)
_cell_length_b                   16.5305(7)
_cell_length_c                   16.9667(8)
_cell_measurement_reflns_used    2674
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.991
_cell_measurement_theta_min      1.720
_cell_volume                     2004.25(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
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_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0316
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11541
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.720
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       plates
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 925 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0478P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2674
_reflns_number_total             3430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00090_si_002.cif
_cod_data_source_block           HH-79b_0m
_cod_database_code               4034337
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              89152
_shelx_hkl_checksum              55693