Enantioselective synthesis of axially chiral biaryls through rhodium-catalyzed complete intermolecular cross-cyclotrimerization of internal alkynes.
Tanaka, Ken; Nishida, Goushi; Ogino, Masakazu; Hirano, Masao; Noguchi, Keiichi; Organic letters 7 (2005) 3119–3121; doi:10.1021/ol0511880

data_1556110
_publ_section_title
;
 Enantioselective synthesis of axially chiral biaryls through
 rhodium-catalyzed complete intermolecular cross-cyclotrimerization of
 internal alkynes.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3119
_journal_page_last               3121
_journal_paper_doi               10.1021/ol0511880
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H21 Br O10 '
_chemical_formula_sum            'C23 H21 Br O10'
_chemical_formula_weight         537.31
_chemical_melting_point          389.1(10)
_chemical_name_common            (-)-(R)-3nb
_chemical_name_systematic
;
 (R)-(-)-6-Acetoxymethyl-2'-bromobiphenyl-2,3,4,5-tetrazcarboxylic
 acid tetramethyl ester
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2005-02-04
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.569(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1105(7)
_cell_length_b                   9.7461(9)
_cell_length_c                   13.7386(11)
_cell_measurement_reflns_used    22178
_cell_measurement_temperature    295
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.3
_cell_volume                     1195.09(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics
'ORTEP-3 for Windows Ver. 1.076 (Farrugia, 1997)'
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22310
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    2.836
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             548.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4114
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0475P)^2^+0.1699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                3852
_reflns_number_total             4114
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0511880si20050520_021540.cif
_cod_data_source_block           3nb
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '115.0-117.0 \%C' was
changed to '389.1(10)' -- it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

 Corrected the value of the '_refine_diff_density_rms' data item
 by removing an ASCII start of heading (SOH) symbol.

 Antanas Vaitkus,
 2019-12-11
;
_cod_original_formula_sum        'C23 H21 Br O10 '
_cod_database_code               1556110