An electrochemical off–on method for pyrimidin-2(1H)-one synthesis via three-component cyclization
Kong, Yanyan; Li, Yabo; Huang, Mengmeng; Kim, Jung Keun; Wu, Yangjie; Green Chemistry 21 (2019) 4495–; doi:10.1039/C9GC02005E

data_7233234
_publ_section_title
;
 An electrochemical off--on method for pyrimidin-2(1H)-one synthesis via
 three-component cyclization
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              4495
_journal_paper_doi               10.1039/C9GC02005E
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_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     direct
_audit_creation_date             2018-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-04 deposited with the CCDC.    2019-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.8682(13)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   17.9538(2)
_cell_length_b                   13.0669(2)
_cell_length_c                   21.0038(3)
_cell_measurement_reflns_used    5915
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2400
_cell_measurement_theta_min      3.3910
_cell_volume                     4892.14(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega  -91.00  -16.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -120.0000 150

  2 omega  -91.00  -39.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   30.0000 104

  3 omega  -47.00   -1.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   30.0000 92

  4 omega -108.00  -68.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   30.0000 80

  5 omega   16.00   57.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 82

  6 omega   58.00   99.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 82

  7 omega    6.00   32.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 52

  8 omega  -34.00   -4.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 60

  9 omega   16.00   95.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   90.0000 158

 10 omega    4.00   33.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -120.0000 58

 11 omega   34.00   59.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 50

 12 omega   42.00   74.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 64

 13 omega   37.00   84.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 94

 14 omega   55.00   91.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 72

 15 omega   43.00  106.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 126

 16 omega   37.00  113.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 152

 17 omega   97.00  175.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 156

 18 omega   56.00   81.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 50

 19 omega   45.00   85.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 80

 20 omega   42.00   68.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 52

 21 omega   42.00   96.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 108

 22 omega   47.00  105.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 116

 23 omega  101.00  153.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 104

 24 omega   70.00   82.50   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0317249000
_diffrn_orient_matrix_UB_12      -0.1038492000
_diffrn_orient_matrix_UB_13      0.0252729000
_diffrn_orient_matrix_UB_21      0.0148402000
_diffrn_orient_matrix_UB_22      0.0449148000
_diffrn_orient_matrix_UB_23      0.0681250000
_diffrn_orient_matrix_UB_31      -0.0790000000
_diffrn_orient_matrix_UB_32      -0.0332589000
_diffrn_orient_matrix_UB_33      0.0132786000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22248
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.845
_diffrn_reflns_theta_min         3.992
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       prism
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         9225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0872P)^2^+0.3333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1660
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6517
_reflns_number_total             9225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc02005e2.cif
_cod_data_source_block           201806272
_cod_depositor_comments          'Adding full bibliography for 7233234.cif.'
_cod_original_cell_volume        4892.17(12)
_cod_database_code               7233234
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.897
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17),
 C18(H18), N1(H1), C8"(H8"), C9"(H9"), C10"(H10"), C11"(H11"), C12"(H12"),
 C14"(H14"), C15"(H15"), C17"(H17"), C18"(H18"), N1"(H1"), C8'(H8'), C9'(H9'),
 C10'(H10'), C11'(H11'), C12'(H12'), C14'(H14'), C15'(H15'), C17'(H17'),
 C18'(H18'), N1'(H1')
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C19(H19A,H19B,H19C), C5"(H5"A,H5"B,H5"C), C19"(H19D,H19E,
 H19F), C5'(H5'A,H5'B,H5'C), C19'(H19G,H19H,H19I)
;
_olex2_submission_special_instructions 'No special instructions were received'