Synthesis of 2,3-dihydro-1H-phosphindole-1-oxides via the t-BuLi-mediated rearrangement of vinyl bromides and phosphine oxides
Li, Bin; Zhang, Mingkai; Huang, Xulun; Gu, Zhenhua; Organic Chemistry Frontiers 4 (2017) 1854–; doi:10.1039/C7QO00310B

data_1553792
_publ_section_title
;
 Synthesis of 2,3-dihydro-1H-phosphindole-1-oxides via the t-BuLi-mediated
 rearrangement of vinyl bromides and phosphine oxides
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1854
_journal_paper_doi               10.1039/C7QO00310B
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C33 H27 O2 P'
_chemical_formula_weight         486.51
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-03-25 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0757(2)
_cell_length_b                   10.4623(2)
_cell_length_c                   26.2445(5)
_cell_measurement_reflns_used    4615
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      71.1530
_cell_measurement_theta_min      4.8670
_cell_volume                     2491.99(9)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6126
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.323
_diffrn_reflns_theta_min         4.550
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.136(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0524P)^2^+0.0971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0843
_reflns_Friedel_coverage         0.579
_reflns_Friedel_fraction_full    0.792
_reflns_Friedel_fraction_max     0.751
_reflns_number_gt                4097
_reflns_number_total             4244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00310b2.cif
_cod_data_source_block           shelxl
_cod_database_code               1553792
_shelx_estimated_absorpt_t_min   0.738
_shelx_estimated_absorpt_t_max   0.778
_shelxl_version_number           2013-4
_shelx_res_checksum              30940
_shelx_hkl_checksum              69861