Selective Hydrogenation of Amides to Amines and Alcohols Catalyzed by Improved Iron Pincer Complexes
Schneck, Felix; Assmann, Maik; Balmer, Markus; Harms, Klaus; Langer, Robert; Organometallics 35 (2016) 1931–; doi:10.1021/acs.organomet.6b00251

data_4088629
_publ_section_title
;
 Selective Hydrogenation of Amides to Amines and Alcohols Catalyzed by
 Improved Iron Pincer Complexes
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              1931
_journal_paper_doi               10.1021/acs.organomet.6b00251
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C29 H29 Br2 Fe N O P2'
_chemical_formula_sum            'C29 H29 Br2 Fe N O P2'
_chemical_formula_weight         685.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.489(3)
_cell_length_b                   17.020(3)
_cell_length_c                   19.647(4)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_volume                     5513.8(18)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1306
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            63936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_min         2.393
_exptl_absorpt_coefficient_mu    3.586
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         6844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0340P)^2^+10.4415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4806
_reflns_number_total             6844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00251_si_003.cif
_cod_data_source_block           platon
_cod_database_code               4088629
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(C2)=Sof(O2)=Sof(Br2)=1-FVAR(1)
 Sof(Br3)=Sof(O1)=Sof(C1)=FVAR(1)
3.a Everything fixed:
 Br3, O1, C1, C2, O2, Br2
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C16(H16A,H16B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C30(H30), C10(H10), C12(H12), C4(H4), C6(H6), C14(H14),
 C26(H26), C28(H28), C13(H13), C8(H8), C20(H20), C21(H21), C22(H22), C29(H29),
 C11(H11), C24(H24), C27(H27), C23(H23)
;
_shelx_res_checksum              53838
_shelx_hkl_checksum              55007
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'