Formamides as Isocyanate Surrogates: A Mechanistically Driven Approach to the Development of Atom-Efficient, Selective Catalytic Syntheses of Ureas, Carbamates, and Heterocycles.
Bruffaerts, Jeffrey; von Wolff, Niklas; Diskin-Posner, Yael; Ben-David, Yehoshoa; Milstein, David; Journal of the American Chemical Society 141 (2019) 16486–16493; doi:10.1021/jacs.9b08942

data_4127684
_publ_section_title
;
 Formamides as Isocyanate Surrogates: A Mechanistically Driven Approach to
 the Development of Atom-Efficient, Selective Catalytic Syntheses of
 Ureas, Carbamates, and Heterocycles.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16486
_journal_page_last               16493
_journal_paper_doi               10.1021/jacs.9b08942
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C26 H46 N2 O2 P2 Ru, C2 H5 N O'
_chemical_formula_sum            'C28 H51 N3 O3 P2 Ru'
_chemical_formula_weight         640.72
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.554(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8308(4)
_cell_length_b                   15.2238(5)
_cell_length_c                   16.2881(6)
_cell_measurement_reflns_used    19951
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.8400
_cell_measurement_theta_min      3.7640
_cell_volume                     3137.48(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41746
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         3.489
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.035
_refine_diff_density_max         1.089
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         9564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0337
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+1.0336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8335
_reflns_number_total             9564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08942_si_002.cif
_cod_data_source_block           m2128a
_cod_database_code               4127684
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              53987
_shelx_hkl_checksum              54009