Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination.
Zhang, Kui; Cai, Lingchao; Yang, Zhongyue; Houk, K. N.; Kwon, Ohyun; Chemical science 9 (2018) 1867–1872; doi:10.1039/c7sc04381c

data_1548722
_publ_section_title
;
 Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic
 \g-umpolung addition-Wittig olefination.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              1867
_journal_page_last               1872
_journal_paper_doi               10.1039/c7sc04381c
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C12 H15 O P'
_chemical_formula_sum            'C12 H15 O P'
_chemical_formula_weight         206.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-07-01 deposited with the CCDC.
2018-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6681(6)
_cell_length_b                   10.3977(7)
_cell_length_c                   11.4123(8)
_cell_measurement_reflns_used    9531
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.13
_cell_measurement_theta_min      3.87
_cell_volume                     1028.57(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9605
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.126
_diffrn_reflns_theta_min         5.756
_diffrn_source                   'I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    2.050
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       rod
_exptl_crystal_F_000             440
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
; 
 Flack x determined using 787 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.032(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.1696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                1939
_reflns_number_total             1950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04381c2.cif
_cod_data_source_block           cu_kwon1503s_a
_cod_depositor_comments          'Adding full bibliography for 1548722.cif.'
_cod_database_code               1548722
_shelxl_version_number           2014/6
_shelx_res_checksum              37739