A general diastereoselective synthesis of highly functionalized ferrocenyl ambiphiles enabled on a large scale by electrochemical purification
Lerayer, Emmanuel; Renaut, Patrice; Roger, Julien; Pirio, Nadine; Cattey, Hélène; Devillers, Charles H.; Lucas, Dominique; Hierso, Jean-Cyrille; Chem. Commun.  (2017) –; doi:10.1039/C7CC02469J

data_7120141
_publ_section_title
;
 A general diastereoselective synthesis of highly functionalized
 ferrocenyl ambiphiles enabled on a large scale by electrochemical
 purification
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02469J
_journal_year                    2017
_chemical_formula_moiety         'C54 H68 B Fe P, C5 H12'
_chemical_formula_sum            'C59 H80 B Fe P'
_chemical_formula_weight         886.86
_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             2017-02-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-02-15 deposited with the CCDC.
2017-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                76.777(3)
_cell_angle_beta                 74.113(3)
_cell_angle_gamma                85.477(4)
_cell_formula_units_Z            2
_cell_length_a                   11.3703(13)
_cell_length_b                   12.9284(14)
_cell_length_c                   18.9441(17)
_cell_measurement_reflns_used    8227
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.04
_cell_volume                     2607.0(5)
_computing_cell_refinement       'SAINT (Bruker, V8.34A,2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, V8.34A,2014)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CMOS
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       '\k-geometry diffractometer triump Mo'
_diffrn_measurement_device_type  'Bruker D8 Venture triumph Mo'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            40154
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.680
_diffrn_reflns_theta_min         2.798
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0681 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.8904.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         11591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0670
_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^)+(0.0786P)^2^+4.7014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7768
_reflns_number_total             11591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc02469j2.cif
_cod_data_source_block           4d
_cod_database_code               7120141
_shelx_shelxl_version_number     2014/7
_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:
 C57(H57a,H57b), C56(H56a,H56b), C58(H58a,H58b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C13(H13), C15(H15),
 C22(H22), C24(H24), C35(H35), C37(H37), C44(H44), C46(H46)
2.c 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), C30(H30a,H30b,H30c), C31(H31a,
 H31b,H31c), C32(H32a,H32b,H32c), C39(H39a,H39b,H39c), C40(H40a,H40b,H40c),
 C41(H41a,H41b,H41c), C48(H48a,H48b,H48c), C49(H49a,H49b,H49c), C50(H50a,H50b,
 H50c), C52(H52a,H52b,H52c), C53(H53a,H53b,H53c), C54(H54a,H54b,H54c), C59(H59a,
 H59b,H59c), C55(H55a,H55b,H55c)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'