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_4087792
_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         'C48 H58 Fe N2 P2'
_chemical_formula_sum            'C48 H58 Fe N2 P2'
_chemical_formula_weight         780.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 101.682(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5890(5)
_cell_length_b                   17.0474(6)
_cell_length_c                   18.6470(7)
_cell_measurement_reflns_used    48457
_cell_measurement_temperature    115
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     4230.2(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.987
_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17776
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         1.194
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     976
_refine_ls_number_reflns         17757
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0706
_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^)+13.7016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                15212
_reflns_number_total             17757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00601_si_002.cif
_cod_data_source_block           comp5
_cod_database_code               4087792
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.49(3) 0.51(3)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C30(H30A,H30B), C59(H59A,H59B), C78(H78A,H78B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C10(H10), C21(H21), C22(H22), C23(H23), C24(H24),
 C25(H25), C19(H19), C18(H18), C17(H17), C16(H16), C15(H15), C38(H38), C37(H37),
  C36(H36), C35(H35), C34(H34), C40(H40), C41(H41), C42(H42), C43(H43),
 C44(H44), C51(H51), C53(H53), C56(H56), C58(H58), C67(H67), C66(H66), C65(H65),
  C64(H64), C63(H63), C73(H73), C72(H72), C71(H71), C70(H70), C69(H69),
 C82(H82), C83(H83), C84(H84), C85(H85), C86(H86), C88(H88), C89(H89), C90(H90),
  C91(H91), C92(H92)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C46(H46A,
 H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C60(H60A,H60B,H60C),
 C61(H61A,H61B,H61C), C75(H75A,H75B,H75C), C76(H76A,H76B,H76C), C77(H77A,H77B,
 H77C), C80(H80A,H80B,H80C), C79(H79A,H79B,H79C), C94(H94A,H94B,H94C), C95(H95A,
 H95B,H95C), C96(H96A,H96B,H96C)
;
_shelx_res_checksum              26881
_shelx_hkl_checksum              3550
_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'