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_1529879
_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            'C14 H12 Br N O'
_chemical_formula_weight         290.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.212(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1858(10)
_cell_length_b                   17.934(3)
_cell_length_c                   11.7423(19)
_cell_measurement_reflns_used    3556
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.72
_cell_measurement_theta_min      2.27
_cell_volume                     1277.8(4)
_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-97 (Sheldrick, 2008)'
_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 1.000
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13636
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    3.199
_exptl_absorpt_correction_T_max  0.8190
_exptl_absorpt_correction_T_min  0.4266
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'APEX2 (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.191
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+2.7849P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                2158
_reflns_number_total             2920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01838_si_003.cif
_cod_data_source_block           mary014
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1529879