Boron trihalide mediated alkyne-aldehyde coupling reactions: a mechanistic investigation.
Kabalka, George W.; Yao, Min-Liang; Borella, Scott; Wu, Zhongzhi; Ju, Yu-Hong; Quick, Travis; The Journal of organic chemistry 73 (2008) 2668–2673; doi:10.1021/jo702493j

data_4029546
_publ_section_title
;
 Boron trihalide mediated alkyne-aldehyde coupling reactions: a
 mechanistic investigation.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2668
_journal_page_last               2673
_journal_paper_doi               10.1021/jo702493j
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C23 H17 Br Cl2'
_chemical_formula_weight         444.18
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_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.957(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.730(2)
_cell_length_b                   13.248(3)
_cell_length_c                   16.912(4)
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.17
_cell_measurement_theta_min      2.53
_cell_volume                     1945.4(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17368
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_diffrn_reflns_theta_max         26.20
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    2.392
_exptl_absorpt_correction_T_max  0.620
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.39
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_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.843
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_refine_ls_number_reflns         3899
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_refine_ls_R_factor_all          0.0375
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.5170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                3442
_reflns_number_total             3899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702493j-file002.cif
_cod_data_source_block           feb10s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4029546