Selective Iron-Catalyzed N-Formylation of Amines using Dihydrogen and Carbon Dioxide
Jayarathne, Upul; Hazari, Nilay; Bernskoetter, Wesley H.; ACS Catalysis 8 (2018) 1338–; doi:10.1021/acscatal.7b03834

data_4514364
_publ_section_title
;
 Selective Iron-Catalyzed N-Formylation of Amines using Dihydrogen and
 Carbon Dioxide
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1338
_journal_paper_doi               10.1021/acscatal.7b03834
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C19 H39 Fe N O2 P2'
_chemical_formula_sum            'C19 H39 Fe N O2 P2'
_chemical_formula_weight         431.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 113.043(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.086(4)
_cell_length_b                   16.908(4)
_cell_length_c                   15.109(3)
_cell_measurement_reflns_used    4533
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.6
_cell_measurement_theta_min      2.6
_cell_volume                     4486.7(17)
_computing_cell_refinement       'SAINT. Ver. 8.34A. (Bruker-AXS, 2014)'
_computing_data_collection       'APEX3. Ver. 2017.3-0.  (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT. Ver. 8.34A. (Bruker-AXS, 2014)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'XL. Ver. 2014/7. (Sheldrick, 2015b)'
_computing_structure_solution    'XT. Ver. 2014/4. (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1504
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            72796
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.450
_diffrn_reflns_theta_min         1.204
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 G\"ottingen, Germany).
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         9182
_refine_ls_number_restraints     602
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0271P)^2^+5.9999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6074
_reflns_number_total             9182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03834_si_002.cif
_cod_data_source_block           UJP2-FeCO2
_cod_depositor_comments
'Adding full bibliography for 4514363--4514365.cif.'
_cod_original_cell_volume        4486.9(17)
_cod_database_code               4514364
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.852
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              35512
_shelx_hkl_checksum              53423