Investigation of the Reductive Cleavage of BINAP and Application to the Rapid Synthesis of Phospholes
Chris W. D. Gallop; Mariusz Bobin; Petra Hourani; Jessica Dwyer; S. Mark Roe; Eddy M. E. Viseux; Journal of Organic Chemistry 78 (2013) 6522–6528; doi:10.1021/jo4006393

data_4028387
_publ_section_title
;
 Investigation of the Reductive Cleavage of BINAP and Application to the
 Rapid Synthesis of Phospholes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6522
_journal_page_last               6528
_journal_paper_doi               10.1021/jo4006393
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H19 O1 P1'
_chemical_formula_sum            'C27 H19 O P'
_chemical_formula_weight         390.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-08-15T10:28:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.133(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7896(3)
_cell_length_b                   8.3870(2)
_cell_length_c                   21.8671(5)
_cell_measurement_reflns_used    18106
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_measurement_wavelength     0.71073
_cell_volume                     1967.48(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.31311E-1
_diffrn_orient_matrix_UB_12      -0.890261E-1
_diffrn_orient_matrix_UB_13      -0.279076E-1
_diffrn_orient_matrix_UB_21      -0.822664E-1
_diffrn_orient_matrix_UB_22      0.551411E-1
_diffrn_orient_matrix_UB_23      -0.82281E-2
_diffrn_orient_matrix_UB_31      0.306749E-1
_diffrn_orient_matrix_UB_32      0.570098E-1
_diffrn_orient_matrix_UB_33      -0.356218E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26933
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.52
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0828P)^2^+0.2375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                3200
_reflns_number_total             4485
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4006393_si_001.cif
_cod_data_source_block           V04CG42D
_cod_original_cell_volume        1967.48(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C27 H19 O1 P1'
_cod_database_code               4028387