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_4087795
_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 H56 Fe N2'
_chemical_formula_sum            'C48 H56 Fe N2'
_chemical_formula_weight         716.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 102.264(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2442(16)
_cell_length_b                   12.3631(10)
_cell_length_c                   17.4252(14)
_cell_measurement_reflns_used    25002
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.92
_cell_measurement_theta_min      4.28
_cell_volume                     4051.2(6)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_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    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture micro Cu'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'QUAZAR MX multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25002
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.920
_diffrn_reflns_theta_max         66.920
_diffrn_reflns_theta_min         4.280
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'high brilliance microfocus sealed tube, Cu'
_exptl_absorpt_coefficient_mu    3.228
_exptl_absorpt_correction_T_max  0.6885
_exptl_absorpt_correction_T_min  0.5480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0791 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.7959.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0329P)^2^+3.9908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3483
_reflns_number_total             3589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00601_si_003.cif
_cod_data_source_block           comp9
_cod_database_code               4087795
_shelx_estimated_absorpt_t_max   0.550
_shelx_estimated_absorpt_t_min   0.381
_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. Uiso/Uaniso restraints and constraints
Uanis(C18B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: C15(0.62) C15B(0.38) C16(0.62) H16(0.62) C16B(0.38) H16B(0.38)
 C17(0.62) H17(0.62) C17B(0.38) H17B(0.38) C18(0.62) H18(0.62) C18B(0.38)
 H18B(0.38) C19(0.62) H19(0.62) C19B(0.38) H19B(0.38) C20(0.62) H20(0.62)
 C20B(0.38) H20B(0.38)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C16B(H16B), C17(H17), C17B(H17B), C18(H18), C18B(H18B), C19(H19),
 C19B(H19B), C20(H20), C20B(H20B)
4.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              16649
_shelx_hkl_checksum              10526
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'