Designing P-Chirogenic 1,2-Diphosphinobenzenes at Both P-Centers Using P(III)-Phosphinites
Bayardon, Jérôme; Rousselin, Yoann; Jugé, Sylvain; Organic Letters  (2016) –; doi:10.1021/acs.orglett.6b01275

data_1543377
_publ_section_title
;
 Designing P-Chirogenic 1,2-Diphosphinobenzenes at Both P-Centers Using
 P(III)-Phosphinites
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.6b01275
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H28 Fe P2'
_chemical_formula_sum            'C34 H28 Fe P2'
_chemical_formula_weight         554.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-04-14
_audit_creation_method
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-04-14 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 107.842(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.3910(6)
_cell_length_b                   8.0519(4)
_cell_length_c                   14.1295(5)
_cell_measurement_reflns_used    2879
_cell_measurement_temperature    115
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1341.92(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4103
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.916
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and acetone by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+1.7127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0712
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4024
_reflns_number_total             4103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01275_si_002.cif
_cod_data_source_block           12j
_cod_database_code               1543377
_publcif_datablock.id            {08d02c6a-e043-4fd3-8b9d-3e9bacc88034}
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.817
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.95(2) 0.05(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C4) = Uanis(C5) = Uanis(C1B) =
Uanis(C2B) = Uanis(C3B) = Uanis(C4B) = Uanis(C5B)
4. Others
 Fixed Sof: C1(0.55) H1(0.55) C2(0.55) H2(0.55) C3(0.55) H3(0.55) C4(0.55)
 H4(0.55) C5(0.55) H5(0.55) C1B(0.45) H1B(0.45) C2B(0.45) H2B(0.45) C3B(0.45)
 H3B(0.45) C4B(0.45) H4B(0.45) C5B(0.45) H5B(0.45)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C1B(H1B), C2B(H2B), C3B(H3B),
 C4B(H4B), C5B(H5B), C6(H6), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24),
  C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32),
 C33(H33), C34(H34)
5.b Fitted pentagon refined as free rotating group:
 C1(C2,C3,C4,C5), C1B(C2B,C3B,C4B,C5B)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre with grease'
_olex2_submission_special_instructions 'No special instructions were received'