Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas: access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones.
Pereshivko, Olga P.; Peshkov, Vsevolod A.; Peshkov, Anatoly A.; Jacobs, Jeroen; Van Meervelt, Luc; Van der Eycken, Erik V.; Organic & biomolecular chemistry 12 (2014) 1741–1750; doi:10.1039/c3ob42221f

data_7153605
_publ_section_title
;
 Unexpected regio- and chemoselectivity of cationic gold-catalyzed
 cycloisomerizations of propargylureas: access to tetrasubstituted
 3,4-dihydropyrimidin-2(1H)-ones.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1741
_journal_page_last               1750
_journal_paper_doi               10.1039/c3ob42221f
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C26 H26 N2 O'
_chemical_formula_sum            'C26 H26 N2 O'
_chemical_formula_weight         382.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-10-16
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_cell_angle_alpha                101.946(8)
_cell_angle_beta                 92.094(8)
_cell_angle_gamma                105.143(12)
_cell_formula_units_Z            2
_cell_length_a                   7.8694(12)
_cell_length_b                   10.0748(12)
_cell_length_c                   13.8855(9)
_cell_measurement_reflns_used    11104
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3132
_cell_measurement_theta_min      2.8798
_cell_volume                     1034.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -45.00  -15.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   77.0000    0.0000 30

  2 omega  -14.00   22.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000   30.0000 36

  3 omega  -85.00    2.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -57.0000  120.0000 87

  4 omega   17.00   52.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   57.0000  -90.0000 35

  5 omega  -17.00   92.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   19.0000   90.0000 109

  6 omega  -10.00   59.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -99.0000  -90.0000 69

  7 omega  -93.00  -35.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513 -178.0000  -90.0000 58

  8 omega  -86.00    4.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -57.0000  -60.0000 90

  9 omega   35.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  178.0000  -60.0000 60

 10 omega   -7.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   38.0000 -120.0000 98

 11 omega  -54.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -38.0000   60.0000 98

 12 omega  -39.00   52.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   57.0000  -90.0000 91

 13 omega  -20.00   25.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000 -150.0000 45

 14 omega  -87.00  -33.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -77.0000   90.0000 54

 15 omega  -20.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -99.0000  150.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0649606000
_diffrn_orient_matrix_UB_12      0.0368444000
_diffrn_orient_matrix_UB_13      0.0099689000
_diffrn_orient_matrix_UB_21      -0.0669965000
_diffrn_orient_matrix_UB_22      -0.0649373000
_diffrn_orient_matrix_UB_23      -0.0107866000
_diffrn_orient_matrix_UB_31      0.0078790000
_diffrn_orient_matrix_UB_32      -0.0037396000
_diffrn_orient_matrix_UB_33      0.0503330000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21403
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.888
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.6322
_exptl_crystal_size_mid          0.4554
_exptl_crystal_size_min          0.1996
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.3131P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3722
_reflns_number_total             4238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3ob42221f.txt
_cod_data_source_block           ev1008
_cod_database_code               7153605
_chemical_oxdiff_formula         'C12 N2 O2 H20'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_hkl_checksum              1467
_shelx_res_checksum              49953
_shelxl_version_number           2012-9