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_4087798
_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         'C52 H62 Fe N2 P2, 0.39(H2 O)'
_chemical_formula_sum            'C52 H62.78 Fe N2 O0.39 P2'
_chemical_formula_weight         839.85
_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   mixed
_atom_sites_solution_primary     iterative
_cell_angle_alpha                81.815(3)
_cell_angle_beta                 79.862(2)
_cell_angle_gamma                66.051(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1411(8)
_cell_length_b                   11.6988(10)
_cell_length_c                   21.3218(17)
_cell_measurement_reflns_used    9714
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.92
_cell_volume                     2268.6(3)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture triumph Mo'
_diffrn_measurement_method       '\f and \w scans'
_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_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            98838
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.921
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0634 before and 0.0548 after correction. The Ratio of minimum to maximum transmission is 0.9543. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         10427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0328P)^2^+1.3892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8317
_reflns_number_total             10427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00601_si_003.cif
_cod_data_source_block           comp15
_cod_database_code               4087798
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.868
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H32A(0.61) H32B(0.61) H32C(0.39) H32D(0.39) N2(0.61) C36(0.61)
 H36A(0.61) H36B(0.61) C35(0.61) H35A(0.61) H35B(0.61) C34(0.61) H34A(0.61)
 H34B(0.61) C33(0.61) H33A(0.61) H33B(0.61) N2B(0.39) C36B(0.39) H36C(0.39)
 H36D(0.39) C35B(0.39) H35C(0.39) H35D(0.39) C34B(0.39) H34C(0.39) H34D(0.39)
 C33B(0.39) H33C(0.39) H33D(0.39) O(0.39) HA(0.39) HB(0.39)
3.a Riding coordinates:
 O(HA,HB)
3.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C32(H32C,H32D), C36(H36A,H36B), C35(H35A,H35B), C34(H34A,
 H34B), C33(H33A,H33B), C36B(H36C,H36D), C35B(H35C,H35D), C34B(H34C,H34D),
 C33B(H33C,H33D), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C9(H9), C21(H21), C20(H20), C19(H19), C18(H18),
 C17(H17), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C38(H38), C39(H39),
  C40(H40), C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
3.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C50(H50A,H50B,
 H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C)
;
_shelx_res_checksum              35680
_shelx_hkl_checksum              32677
_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'