N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Aldehydes with Carbodiimides under Aerobic Conditions: Efficient Synthesis ofN-Acylureas
Soeta, Takahiro; Tabatake, Yuhta; Fujinami, Shuhei; Ukaji, Yutaka; Organic Letters 15 (2013) 2088–; doi:10.1021/ol400672c

data_1511940
_publ_section_title
;
 N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Aldehydes with
 Carbodiimides under Aerobic Conditions: Efficient Synthesis ofN-Acylureas
;
_journal_issue                   9
_journal_name_full               'Organic Letters'
_journal_page_first              2088
_journal_paper_doi               10.1021/ol400672c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C20 H21 Cl N2 O2 '
_chemical_formula_sum            'C20 H21 Cl N2 O2'
_chemical_formula_weight         356.85
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.492(1)
_cell_length_b                   12.566(1)
_cell_length_c                   11.401(1)
_cell_measurement_reflns_used    6469
_cell_measurement_temperature    123.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     1789.7(3)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      123.2
_diffrn_detector_area_resol_mean 14.46
_diffrn_measured_fraction_theta_full 0.9815
_diffrn_measured_fraction_theta_max 0.9815
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2322
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             752.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3316
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.0012
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0317
_reflns_number_gt                3316
_reflns_number_total             2126
_reflns_threshold_expression     F^2^>3.0\s(F^2^)
_cod_data_source_file            ol400672c_si_002.cif
_cod_data_source_block           '_tabatake9'
_cod_original_cell_volume        1789.6(6)
_cod_original_sg_symbol_H-M      'P n a 21     '
_cod_original_formula_sum        'C20 H21 Cl N2 O2 '
_cod_database_code               1511940