Diastereoselective, Zinc-Catalyzed Alkynylation of α-Bromo Oxocarbenium Ions.
Haidzinskaya, Tatsiana; Kerchner, Hilary A.; Liu, Jixin; Watson, Mary P.; Organic letters 17 (2015) 3857–3859; doi:10.1021/acs.orglett.5b01838

data_1529880
_publ_section_title
;
 Diastereoselective, Zinc-Catalyzed Alkynylation of \a-Bromo Oxocarbenium
 Ions.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3857
_journal_page_last               3859
_journal_paper_doi               10.1021/acs.orglett.5b01838
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C12 H13 Br O3'
_chemical_formula_weight         285.13
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.1530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.79830(10)
_cell_length_b                   8.1321(2)
_cell_length_c                   24.8527(6)
_cell_measurement_reflns_used    9234
_cell_measurement_temperature    200(2)
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_cell_measurement_theta_min      2.64
_cell_volume                     1171.86(5)
_computing_cell_refinement       'Bruker SAINT'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
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_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_l_min       -32
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.733
_diffrn_reflns_theta_min         1.639
_exptl_absorpt_coefficient_mu    3.497
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2007)'
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
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_exptl_crystal_size_min          0.116
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_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0230
_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^)+(0.0329P)^2^+0.4073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
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_reflns_number_total             2752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01838_si_002.cif
_cod_data_source_block           mary025a
_cod_database_code               1529880
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.331
_shelx_estimated_absorpt_t_max   0.687
_shelx_res_checksum              75283
_shelx_hkl_checksum              52035