Carbolithiation of Diphenylacetylene as a Stereoselective Route to (Z)-Tamoxifen and Related Tetrasubstituted Olefins
Neola F. McKinley; Donal F. O'Shea; Journal of Organic Chemistry 71 (2006) 9552–9555; doi:10.1021/jo061949s

data_4022170
_publ_section_title
;
 Carbolithiation of Diphenylacetylene as a Stereoselective Route
 to (Z)-Tamoxifen and Related Tetrasubstituted Olefins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9552
_journal_page_last               9555
_journal_paper_doi               10.1021/jo061949s
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C16 H17 B O2'
_chemical_formula_weight         252.11
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 101.330(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.871(4)
_cell_length_b                   5.2129(11)
_cell_length_c                   30.632(6)
_cell_measurement_reflns_used    3770
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      2.32
_cell_volume                     2798.1(10)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6928
_diffrn_reflns_theta_full        21.99
_diffrn_reflns_theta_max         21.99
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.7891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0833
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+9.0802P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1949
_refine_ls_wR_factor_ref         0.1981
_reflns_number_gt                1589
_reflns_number_total             1728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061949ssi20060921_075048.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022170