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_4514363
_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         'C23 H47 Fe N2 O3 P2'
_chemical_formula_sum            'C23 H47 Fe N2 O3 P2'
_chemical_formula_weight         517.41
_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                 91.1460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3360(13)
_cell_length_b                   12.2113(10)
_cell_length_c                   27.367(2)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.2
_cell_volume                     5458.2(7)
_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 0.998
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            85608
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         1.247
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.86
_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            Orange
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.093
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         13556
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+7.9027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11184
_reflns_number_total             13556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03834_si_003.cif
_cod_data_source_block           UJP2_Rst
_cod_depositor_comments
'Adding full bibliography for 4514363--4514365.cif.'
_cod_original_cell_volume        5458.2(8)
_cod_database_code               4514363
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.793
_shelx_estimated_absorpt_t_max   0.934
_shelx_res_checksum              72286
_shelx_hkl_checksum              35272