NHC-stabilized gold(I) complexes: suitable catalysts for 6-exo-dig heterocyclization of 1-(o-ethynylaryl)ureas.
Gimeno, Ana; Medio-Simón, Mercedes; de Arellano, Carmen Ramírez; Asensio, Gregorio; Cuenca, Ana B.; Organic letters 12 (2010) 1900–1903; doi:10.1021/ol100595s

data_1502953
_publ_section_title
;
 NHC-stabilized gold(I) complexes: suitable catalysts for 6-exo-dig
 heterocyclization of 1-(o-ethynylaryl)ureas.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1900
_journal_page_last               1903
_journal_paper_doi               10.1021/ol100595s
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27
_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                 92.715(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9132(5)
_cell_length_b                   6.9003(3)
_cell_length_c                   15.2690(7)
_cell_measurement_reflns_used    3730
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.1335
_cell_measurement_theta_min      2.3401
_cell_volume                     1148.53(9)
_computing_cell_refinement       'CrysAlisPro (Oxford Diff., 2009)'
_computing_data_collection       'CrysAlisPro (Oxford Diff., 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diff., 2009)'
_computing_molecular_graphics    'CrystalMaker 2.1.5 (1994-2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.0267
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device_type  'Oxford Diffr. Gemini S'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11878
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Oxford Diff., 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0390P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                1672
_reflns_number_total             2768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100595s_si_002.cif
_cod_data_source_block           ag1976_compound2a
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1502953