Metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene ortho-quinone methide (VQM).
Huang, Shengli; Chen, Zhili; Mao, Hui; Hu, Fangli; Li, Dongmei; Tan, Yu; Yang, Fengqing; Qin, Wenling; Organic & biomolecular chemistry 17 (2019) 1121–1129; doi:10.1039/c8ob02967a

data_7156644
_publ_section_title
;
 Metal-free difunctionalization of alkynes to access tetrasubstituted
 olefins through spontaneous selenosulfonylation of vinylidene
 ortho-quinone methide (VQM).
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1121
_journal_page_last               1129
_journal_paper_doi               10.1039/c8ob02967a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C31 H23 Br O3 S Se'
_chemical_formula_sum            'C31 H23 Br O3 S Se'
_chemical_formula_weight         634.42
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-29
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_audit_update_record
;
2018-11-07 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.020(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8543(4)
_cell_length_b                   12.8156(3)
_cell_length_c                   16.9743(5)
_cell_measurement_reflns_used    6525
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.8520
_cell_measurement_theta_min      3.7170
_cell_volume                     3120.95(15)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.6296
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17250
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.255
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0600P)^2^+1.1719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4724
_reflns_number_total             6378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02967a2.cif
_cod_data_source_block           236_sq
_cod_depositor_comments          'Adding full bibliography for 7156644.cif.'
_cod_original_cell_volume        3120.94(15)
_cod_database_code               7156644
_shelx_shelxl_version_number     2014/7
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C4(H4), C30(H30), C29(H29), C27(H27), C6(H6), C11(H11), C25(H25),
 C15(H15), C3(H3A), C21(H21), C17(H17), C7(H7), C12(H12), C20(H20), C19(H19),
 C18(H18), C14(H14), C13(H13)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'