N-Heterocyclic carbene-catalyzed annulation of ynals with amidines: access to 1,2,6-trisubstituted pyrimidin-4-ones.
Xie, Yangxi; Wang, Jian; Chemical communications (Cambridge, England) 54 (2018) 4597–4600; doi:10.1039/c8cc02023j

data_7121485
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed annulation of ynals with amidines:
 access to 1,2,6-trisubstituted pyrimidin-4-ones.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4597
_journal_page_last               4600
_journal_paper_doi               10.1039/c8cc02023j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C22 H16 N2 O'
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-15 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.166(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.5316(6)
_cell_length_b                   6.70060(10)
_cell_length_c                   24.2907(6)
_cell_measurement_reflns_used    4925
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9570
_cell_measurement_theta_min      5.7880
_cell_volume                     3466.51(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -109.00 -22.00   1.00    2.50    --  -40.81 -38.00  30.00   87
  2  \w   -102.00 -13.00   1.00    2.50    --  -40.81 -57.00 120.00   89
  3  \w    -98.00 -71.00   1.00    2.50    --  -40.81-134.00-145.00   27
  4  \w     12.00  55.00   1.00    2.50    --   40.81 -57.00  30.00   43
  5  \w     42.00 107.00   1.00   10.50    --  100.91 -95.00 -90.00   65
  6  \w    110.00 143.00   1.00   10.50    --  100.91 125.00 -60.00   33
  7  \w     60.00 170.00   1.00   10.50    --  100.91  15.00 150.00  110
  8  \w    149.00 174.00   1.00   10.50    --  100.91 125.00 -60.00   25
  9  \w     44.00 129.00   1.00   10.50    --  100.91 -30.00 -60.00   85
 10  \w    127.00 174.00   1.00   10.50    --  100.91 125.00 -30.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0473328000
_diffrn_orient_matrix_UB_12      -0.0537605000
_diffrn_orient_matrix_UB_13      -0.0261102000
_diffrn_orient_matrix_UB_21      -0.0523194000
_diffrn_orient_matrix_UB_22      0.0195721000
_diffrn_orient_matrix_UB_23      -0.0650153000
_diffrn_orient_matrix_UB_31      0.0160288000
_diffrn_orient_matrix_UB_32      0.2226684000
_diffrn_orient_matrix_UB_33      -0.0005921000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12227
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.522
_diffrn_reflns_theta_min         3.658
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+0.5720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5139
_reflns_number_total             6491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc02023j2.cif
_cod_data_source_block           20171026xieyangxi
_cod_depositor_comments          'Adding full bibliography for 7121485.cif.'
_cod_original_cell_volume        3466.50(15)
_cod_database_code               7121485
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C202(H202), C102(H102), C216(H216), C118(H118), C122(H122), C212(H212),
 C112(H112), C116(H116), C215(H215), C214(H214), C213(H213), C121(H121),
 C119(H119), C120(H120), C113(H113), C115(H115), C206(H206), C222(H222),
 C210(H210), C110(H110), C114(H114), C208(H208), C220(H220), C207(H207),
 C218(H218), C221(H221), C209(H209), C106(H106), C108(H108), C219(H219),
 C109(H109), C107(H107)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.659