Acetoacetanilides as masked isocyanates: facile and efficient synthesis of unsymmetrically substituted ureas
Wei, Ying; Liu, Jing; Lin, Shaoxia; Ding, Hongqian; Liang, Fushun; Zhao, Baozhong; Organic Letters 12 (2010) 4220–4223; doi:10.1021/ol101474f

data_1513315
_publ_section_title
;
 Acetoacetanilides as masked isocyanates: facile and efficient synthesis
 of unsymmetrically substituted ureas
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   19
_journal_name_full               'Organic Letters'
_journal_page_first              4220
_journal_page_last               4223
_journal_paper_doi               10.1021/ol101474f
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C11 H14 N2 O'
_chemical_formula_weight         190.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.162(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.925(5)
_cell_length_b                   13.408(7)
_cell_length_c                   17.122(9)
_cell_measurement_reflns_used    3760
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      1.93
_cell_volume                     2048.5(19)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  'SHELXTL (Bruker, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1417
_diffrn_reflns_av_sigmaI/netI    0.2219
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10209
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.45
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.2740
_refine_ls_R_factor_gt           0.0790
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1159P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.2817
_reflns_number_gt                1116
_reflns_number_total             3760
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             1503124
_cod_data_source_file            ol101474fsup1.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-20

 Marked entry as a duplicate of entry 1503124.

 Antanas Vaitkus,
 2019-09-20

2025-01-26
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C22 H28 N4 O2'
_cod_original_formula_weight         380.48
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2048.5(18)
_cod_original_sg_symbol_H-M      p2(1)/c
_cod_database_code               1513315