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_4087787
_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         'C44 H50 Fe N2 P2'
_chemical_formula_sum            'C44 H50 Fe N2 P2'
_chemical_formula_weight         724.65
_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
_cell_angle_alpha                67.987(2)
_cell_angle_beta                 80.662(3)
_cell_angle_gamma                87.627(3)
_cell_formula_units_Z            2
_cell_length_a                   11.5610(4)
_cell_length_b                   12.3228(6)
_cell_length_c                   14.7532(7)
_cell_measurement_temperature    115
_cell_volume                     1922.32(15)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_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 0.981
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius 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  0.0533
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15489
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         2.712
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.355
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         8590
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.1372
_refine_ls_R_factor_gt           0.0899
_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^)+(0.0356P)^2^+6.4574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.2008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5863
_reflns_number_total             8590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00601_si_004.cif
_cod_data_source_block           comp12'
_cod_database_code               4087787
_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. Same fragment restrains
{N1, C11, C12, C13, C14, C15} sigma for 1-2: 0.02, 1-3: 0.04
as
{N2, C28, C29, C30, C31, C32}
{N1, C11, C14, C15, C12, C13} sigma for 1-2: 0.02, 1-3: 0.04
as
{N2B, C28B, C29B, C30B, C31B, C32B}
3. Others
 Uiso(C28B)=FVAR(1)
 Uiso(N2B)=1.17*FVAR(2)
 Uiso(C29B)=Uiso(C31B)=1.57*FVAR(2)
 Uiso(C30B)=Uiso(C32B)=2.6*FVAR(2)
 Fixed Sof: N2(0.7) C28(0.7) H28A(0.7) H28B(0.7) C29(0.7) H29A(0.7) H29B(0.7)
 C30(0.7) H30A(0.7) H30B(0.7) H30C(0.7) C31(0.7) H31A(0.7) H31B(0.7) C32(0.7)
 H32A(0.7) H32B(0.7) H32C(0.7) N2B(0.3) C28B(0.3) H28C(0.3) H28D(0.3) C29B(0.3)
 H29C(0.3) H29D(0.3) C30B(0.3) H30D(0.3) H30E(0.3) H30F(0.3) C31B(0.3)
 H31C(0.3) H31D(0.3) C32B(0.3) H32D(0.3) H32E(0.3) H32F(0.3)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C12(H12A,H12B), C28(H28A,H28B), C29(H29A,
 H29B), C31(H31A,H31B), C28B(H28C,H28D), C29B(H29C,H29D), C31B(H31C,H31D)
4.b Me refined with riding coordinates:
 C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C30B(H30D,H30E,H30F), C32B(H32D,
 H32E,H32F)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              36197
_shelx_hkl_checksum              86826
_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'