Planar-Chiral 1,1'-Diboryl Metallocenes: Diastereoselective Synthesis from Boryl Cyclopentadienides and Spin Density Analysis of a Diborylcobaltocene.
Lerayer, Emmanuel; Renaut, Patrice; Brandès, Stéphane; Cattey, Hélène; Fleurat-Lessard, Paul; Bouhadir, Ghenwa; Bourissou, Didier; Hierso, Jean-Cyrille; Inorganic chemistry 56 (2017) 1966–1973; doi:10.1021/acs.inorgchem.6b02510

data_4345078
_publ_section_title
;
 Planar-Chiral 1,1'-Diboryl Metallocenes: Diastereoselective Synthesis
 from Boryl Cyclopentadienides and Spin Density Analysis of a
 Diborylcobaltocene.
;
_journal_issue                   4
_journal_name_full               'Inorganic chemistry'
_journal_page_first              1966
_journal_page_last               1973
_journal_paper_doi               10.1021/acs.inorgchem.6b02510
_journal_volume                  56
_journal_year                    2017
_chemical_formula_moiety         'C54 H68 B2 Fe, 0.5 (C6 H14)'
_chemical_formula_sum            'C57 H75 B2 Fe'
_chemical_formula_weight         837.64
_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
_audit_update_record
;
2016-04-13 # Formatted by publCIF

;
_cell_angle_alpha                88.893(1)
_cell_angle_beta                 87.091(1)
_cell_angle_gamma                77.896(1)
_cell_formula_units_Z            2
_cell_length_a                   10.0641(2)
_cell_length_b                   13.7226(3)
_cell_length_c                   18.0150(4)
_cell_measurement_reflns_used    22847
_cell_measurement_temperature    115
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2429.43(9)
_computing_cell_refinement       'SAINT (Bruker, V8.34A,2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, V8.34A,2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       '\f and \w scans'
_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_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36565
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.397
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  0.9434
_exptl_absorpt_correction_T_min  0.8907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
;
_exptl_crystal_colour            'light red'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             906
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         11056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0436P)^2^+2.3323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9576
_reflns_number_total             11056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic6b02510_si_001.cif
_cod_data_source_block           compound_6a
_cod_depositor_comments
'Adding full bibliography for 4345078--4345079.cif.'
_cod_database_code               4345078
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B), C56(H56A,H56B)
2.b Me refined with riding coordinates:
 C57(H57A,H57B,H57C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C9(H9), C10(H10), C13(H13), C15(H15),
 C22(H22), C24(H24), C35(H35), C37(H37), C44(H44), C46(H46)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C39(H39A,H39B,H39C), C40(H40A,
 H40B,H40C), C41(H41A,H41B,H41C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C),
 C50(H50A,H50B,H50C)
;
_shelx_res_checksum              83129
_shelx_hkl_checksum              5823
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with grease'
_olex2_submission_special_instructions 'No special instructions were received'