Nickel-catalyzed asymmetric ring opening of oxabenzonorbornadienes with arylboronic acids.
Zeng, Zhongyi; Yang, Dingqiao; Long, Yuhua; Pan, Xuejing; Huang, Guobao; Zuo, Xiongjun; Zhou, Wen; The Journal of organic chemistry 79 (2014) 5249–5257; doi:10.1021/jo500821m

data_4029459
_publ_section_title
;
 Nickel-catalyzed asymmetric ring opening of oxabenzonorbornadienes with
 arylboronic acids.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5249
_journal_page_last               5257
_journal_paper_doi               10.1021/jo500821m
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C18 H17 Cl O3'
_chemical_formula_sum            'C18 H17 Cl O3'
_chemical_formula_weight         316.77
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.878(2)
_cell_length_b                   16.418(7)
_cell_length_c                   19.847(9)
_cell_measurement_reflns_used    2867
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      1.61
_cell_measurement_theta_min      25.24
_cell_volume                     1589.5(12)
_computing_cell_refinement       'Apex2 (Bruker, 2005)'
_computing_data_collection       'Apex2 (Bruker, 2005)'
_computing_data_reduction        'Apex2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL 6.12'
_computing_publication_material  'SHELXTL 6.12'
_computing_structure_refinement  'SHELXTL 6.12'
_computing_structure_solution    'SHELXTL 6.12 (Bruker, 2000-2003)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\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  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0800
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8116
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.21(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                1276
_reflns_number_total             2867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500821m_si_002.cif
_cod_data_source_block           re
_cod_depositor_comments          'Adding full bibliography for 4029459.cif.'
_cod_database_code               4029459