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_4127683
_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         'C25 H44 N2 O2 P2 Ru'
_chemical_formula_sum            'C25 H44 N2 O2 P2 Ru'
_chemical_formula_weight         567.63
_space_group_crystal_system      monoclinic
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_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                 91.429(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3292(5)
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_cell_length_c                   16.1689(6)
_cell_measurement_reflns_used    19900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.7450
_cell_measurement_theta_min      3.7200
_cell_volume                     2742.58(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
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_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 offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
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_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
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_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
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_diffrn_reflns_theta_max         33.140
_diffrn_reflns_theta_min         3.394
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_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.806
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_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (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            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       needle
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_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.025
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_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         10434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0331
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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^)+(0.0217P)^2^+0.7539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                8884
_reflns_number_total             10434
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           m2106a
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_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              15112
_shelx_hkl_checksum              77157