Converging and Diverging Synthetic Strategies to Tetradentate (N,N′)-Diaminomethyl,(P,P′)-Ferrocenyl Ligands: Influence of tert-Butyl Groups on Ferrocene Backbone Conformation
Allouch, Fatima; Dwadnia, Nejib; Vologdin, Nikolay V.; Svyaschenko, Yurii V.; Cattey, Hélène; Penouilh, Marie-José; Roger, Julien; Naoufal, Daoud; Ben Salem, Ridha; Pirio, Nadine; Hierso, Jean-Cyrille; Organometallics 34 (2015) 5015–; doi:10.1021/acs.organomet.5b00601

data_4087794
_publ_section_title
;
 Converging and Diverging Synthetic Strategies to Tetradentate
 (N,N&#x2032;)-Diaminomethyl,(P,P&#x2032;)-Ferrocenyl Ligands: Influence
 of tert-Butyl Groups on Ferrocene Backbone Conformation
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5015
_journal_paper_doi               10.1021/acs.organomet.5b00601
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C30 H48 Fe N2'
_chemical_formula_sum            'C30 H48 Fe N2'
_chemical_formula_weight         492.55
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                88.841(2)
_cell_angle_beta                 69.140(2)
_cell_angle_gamma                75.500(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2309(6)
_cell_length_b                   11.0502(5)
_cell_length_c                   13.2511(7)
_cell_measurement_reflns_used    9649
_cell_measurement_temperature    115
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.22
_cell_volume                     1351.36(13)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius,1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_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-2013 (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 0.992
_diffrn_measured_fraction_theta_max 0.987
_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  0.0336
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22956
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.599
_diffrn_reflns_theta_min         1.909
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0489 before and 0.0432 after correction.
The Ratio of minimum to maximum transmission is 0.9324.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         6195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0472P)^2^+1.1058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5357
_reflns_number_total             6195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00601_si_003.cif
_cod_data_source_block           comp8
_cod_original_cell_volume        1351.36(12)
_cod_database_code               4087794
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.802
_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:
 C26(H26A,H26B), C16(H16A,H16B), C24(H24A,H24B), C22(H22A,H22B), C13(H13A,
 H13B), C11(H11A,H11B), C25(H25A,H25B), C12(H12A,H12B), C21(H21A,H21B),
 C23(H23A,H23B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C8(H8), C7(H7), C2(H2), C5(H5)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C30(H30A,H30B,H30C), C29(H29A,H29B,H29C), C28(H28A,H28B,
 H28C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              33393
_shelx_hkl_checksum              96492
_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'