Silver-catalyzed three-component reaction of uracils, arylboronic acids, and selenium: synthesis of 5-arylselanyluracils
Murata, Yuki; Tsuchida, Saori; Nezaki, Rena; Kitamura, Yuki; Matsumura, Mio; Yasuike, Shuji; RSC Advances 12 (2022) 14502–14508; doi:10.1039/D2RA01685K

data_7244942
_publ_section_title
;
 Silver-catalyzed three-component reaction of uracils, arylboronic acids,
 and selenium: synthesis of 5-arylselanyluracils
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              14502
_journal_page_last               14508
_journal_paper_doi               10.1039/D2RA01685K
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C12 H12 N2 O2 Se'
_chemical_formula_sum            'C12 H12 N2 O2 Se'
_chemical_formula_weight         295.20
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-06-29 deposited with the CCDC.	2022-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.7340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   12.30260(10)
_cell_length_b                   10.19280(10)
_cell_length_c                   56.9658(4)
_cell_measurement_reflns_used    25070
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.2530
_cell_measurement_theta_min      2.3230
_cell_volume                     7119.02(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_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     24.00  62.00   0.38    0.20    --   40.27  23.00 -54.00  100
  2  \w     63.00  89.22   0.38    0.20    --   40.27  23.00 -54.00   69
  3  \w     82.00 107.08   0.38    0.21    --   96.04  23.00 -54.00   66
  4  \w    131.00 157.22   0.38    0.21    --   96.04  23.00 -54.00   69
  5  \w    133.00 159.22   0.38    0.21    --   96.04  50.00-120.00   69
  6  \w    134.00 158.70   0.38    0.21    --   96.04  33.00-120.00   65
  7  \w    100.00 127.36   0.38    0.21    --   96.04  50.00-120.00   72
  8  \w     84.00 114.78   0.38    0.21    --   96.04  33.00-120.00   81
  9  \w     71.00 106.72   0.38    0.21    --   96.04  77.00-180.00   94
 10  \w     29.00  55.22   0.38    0.21    --   96.04 -50.00 -90.00   69
 11  \w     50.00  96.36   0.38    0.21    --   96.04 -96.00 -60.00  122
 12  \w     63.00  93.78   0.38    0.20    --   40.27-138.00  30.00   81
 13  \w     33.00  59.22   0.38    0.20    --   40.27-138.00  30.00   69
 14  \w     30.00  68.00   0.38    0.21    --   96.04 -59.00 150.00  100
 15  \w     29.00  54.08   0.38    0.21    --   96.04 -50.00 120.00   66
 16  \w     29.00  56.36   0.38    0.21    --   96.04 -50.00  90.00   72
 17  \w    -29.00  -3.92   0.38    0.20    --   40.27 -23.00 140.00   66
 18  \w    -23.00  41.22   0.38    0.20    --   40.27 -37.00  90.00  169
 19  \w    -25.00  16.04   0.38    0.20    --   40.27 -12.00 -30.00  108
 20  \w    -34.00  -8.92   0.38    0.20    --   40.27 -12.00 -60.00   66
 21  \w    -34.00  20.34   0.38    0.20    --   40.27 -12.00   0.00  143
 22  \w    -34.00  21.86   0.38    0.20    --   40.27 -12.00  60.00  147
 23  \w    -64.00  -9.66   0.38    0.20    --  -40.58  77.00 -30.00  143
 24  \w     -1.00  24.08   0.38    0.20    --  -40.58  77.00 -30.00   66
 25  \w     -8.00  18.22   0.38    0.20    --  -40.58  63.00-120.00   69
 26  \w     -1.00  24.08   0.38    0.20    --  -40.58  23.00 -54.00   66
 27  \w    -57.00 -30.78   0.38    0.21    --  -96.35  50.00  60.00   69
 28  \w    -66.00 -31.80   0.38    0.21    --  -96.35  59.00  60.00   90
 29  \w    -69.00 -34.80   0.38    0.21    --  -96.35  59.00  90.00   90
 30  \w    -69.00 -42.78   0.38    0.21    --  -96.35  59.00  30.00   69
 31  \w    -78.00 -33.92   0.38    0.21    --  -96.35  68.00   0.00  116
 32  \w    -71.00 -33.76   0.38    0.21    --  -96.35 117.00 -30.00   98
 33  \w    -79.00  -7.94   0.38    0.20    --  -40.58 104.00 -30.00  187
 34  \w    -68.00 -43.68   0.38    0.21    --  -96.35 117.00  90.00   64
 35  \w   -113.00 -85.64   0.38    0.21    --  -96.35 117.00 -30.00   72
 36  \w   -113.00 -82.22   0.38    0.21    --  -96.35 117.00  90.00   81
 37  \w   -117.00 -81.66   0.38    0.21    --  -96.35 -23.00 140.00   93
 38  \w    -52.00 -27.68   0.38    0.20    --  -40.58 -23.00 140.00   64
 39  \w    -86.00 -61.68   0.38    0.20    --  -40.58-138.00 120.00   64
 40  \w   -141.00 -77.92   0.38    0.21    --  -96.35 -50.00  30.00  166
 41  \w   -101.00 -77.06   0.38    0.20    --  -40.58 -23.00 140.00   63
 42  \w   -163.00 -89.28   0.38    0.21    --  -96.35 -33.00 120.00  194
 43  \w     68.00  93.08   0.38    0.20    --   40.27-138.00-150.00   66
 44  \w     31.00  82.30   0.38    0.21    --   96.04 -68.00-150.00  135
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1080703000
_diffrn_orient_matrix_UB_12      0.0331463000
_diffrn_orient_matrix_UB_13      -0.0105256000
_diffrn_orient_matrix_UB_21      -0.0630935000
_diffrn_orient_matrix_UB_22      0.0308670000
_diffrn_orient_matrix_UB_23      -0.0238490000
_diffrn_orient_matrix_UB_31      -0.0113634000
_diffrn_orient_matrix_UB_32      0.1442006000
_diffrn_orient_matrix_UB_33      0.0075320000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       65
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_number            38140
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.404
_diffrn_reflns_theta_min         3.114
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
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    1.653
_exptl_crystal_description       prism
_exptl_crystal_F_000             3552
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     931
_refine_ls_number_reflns         12880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.237
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0248P)^2^+16.3893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12272
_reflns_number_total             12880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra01685k2.cif
_cod_data_source_block           201119mat1
_cod_original_cell_volume        7119.03(10)
_cod_database_code               7244942
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H12 N2 O2 Se1'
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1E(H1E), C12E(H12E), C8D(H8D), C9F(H9F), C1B(H1B), C8E(H8E), C1F(H1F),
 C13F(H13F), C12D(H12D), C8C(H8C), C1D(H1D), C8A(H8A), C1C(H1C), C12C(H12C),
 C9C(H9C), C9E(H9E), C11E(H11E), C12A(H12A), C10E(H10E), C1A(H1A), C8B(H8B),
 C10D(H10D), C9A(H9A), C10F(H10F), C9D(H9D), C11F(H11F), C7F(H7F), C12F(H12F),
 C11A(H11A), C10C(H10C), C11D(H11D), C9B(H9B), C11C(H11C), C12B(H12B),
 C10B(H10B), C11B(H11B)
2.b Idealised Me refined as rotating group:
 C2F(H2FA,H2FB,H2FC), C4F(H4FA,H4FB,H4FC), C4D(H4DA,H4DB,H4DC), C4C(H4CA,H4CB,
 H4CC), C4E(H4EA,H4EB,H4EC), C2D(H2DA,H2DB,H2DC), C4A(H4AA,H4AB,H4AC), C2C(H2CA,
 H2CB,H2CC), C2B(H2BA,H2BB,H2BC), C2A(H2AA,H2AB,H2AC), C4B(H4BA,H4BB,H4BC),
 C2E(H2EA,H2EB,H2EC)
;
_shelx_res_checksum              13795
_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 1.248
_oxdiff_exptl_absorpt_empirical_full_min 0.821