Planar Polycyclic Oxaphosphoranes Incorporating a Benzophosphole Unit.
Zhao, Xu; Gan, Zhenjie; Hu, Chaopeng; Duan, Zheng; Mathey, François; Organic letters 19 (2017) 5814–5817; doi:10.1021/acs.orglett.7b02769

data_1547675
_publ_section_title
;
 Planar Polycyclic Oxaphosphoranes Incorporating a Benzophosphole Unit.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5814
_journal_page_last               5817
_journal_paper_doi               10.1021/acs.orglett.7b02769
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C33 H25 O P'
_chemical_formula_sum            'C33 H25 O P'
_chemical_formula_weight         468.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.361(3)
_cell_angle_beta                 108.098(3)
_cell_angle_gamma                97.969(3)
_cell_formula_units_Z            4
_cell_length_a                   12.3745(4)
_cell_length_b                   13.9516(5)
_cell_length_c                   15.5108(6)
_cell_measurement_reflns_used    5759
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1050
_cell_measurement_theta_min      3.8420
_cell_volume                     2517.32(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -25.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000   60.0000 49

  2 omega   13.00   72.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   57.0000  -60.0000 59

  3 omega  -13.00   35.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000  -60.0000 48

  4 omega  -47.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000  120.0000 45

  5 omega  -21.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -99.0000 -180.0000 54

  6 omega  -18.00   56.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -99.0000 -120.0000 74

  7 omega   -1.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   37.0000   90.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0415836000
_diffrn_orient_matrix_UB_12      0.0003825000
_diffrn_orient_matrix_UB_13      0.0435227000
_diffrn_orient_matrix_UB_21      -0.0185226000
_diffrn_orient_matrix_UB_22      0.0417403000
_diffrn_orient_matrix_UB_23      0.0138424000
_diffrn_orient_matrix_UB_31      -0.0406315000
_diffrn_orient_matrix_UB_32      -0.0300645000
_diffrn_orient_matrix_UB_33      0.0154428000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21658
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.476
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.898
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         10308
_refine_ls_number_restraints     244
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0759
_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^)+(0.0914P)^2^+2.0874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2119
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6883
_reflns_number_total             10308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02769_si_004.cif
_cod_data_source_block           20160586
_cod_depositor_comments
'Adding full bibliography for 1547674--1547677.cif.'
_cod_original_cell_volume        2517.31(16)
_cod_database_code               1547675
_chemical_oxdiff_formula         C1H1O1N1P1
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(P1) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(P1') \\sim Ueq, Uanis(C10') \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C2'(H2'),
 C3'(H3'), C4'(H4'), C5'(H5'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'),
 C16'(H16'), C17'(H17'), C19'(H19'), C20'(H20'), C23'(H23'), C24'(H24'),
 C25'(H25'), C26'(H26'), C27'(H27'), C29'(H29'), C30'(H30'), C31'(H31'),
 C32'(H32'), C33'(H33')
4.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21'(H21D,H21E,H21F)
;
_shelx_res_checksum              95201
_shelx_hkl_checksum              40359
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'