Metal carbonyl mediated rearrangement of 5-(2-oxoalkyl)-1,2,4-oxadiazoles: synthesis of fully substituted pyrimidines.
Galenko, Ekaterina E.; Zanakhov, Timur O.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Organic & biomolecular chemistry 21 (2023) 2990–3001; doi:10.1039/d3ob00148b

data_7159243
_publ_section_title
;
 Metal carbonyl mediated rearrangement of
 5-(2-oxoalkyl)-1,2,4-oxadiazoles: synthesis of fully substituted
 pyrimidines.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2990
_journal_page_last               3001
_journal_paper_doi               10.1039/d3ob00148b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C20 H17 F N2 O4'
_chemical_formula_sum            'C20 H17 F N2 O4'
_chemical_formula_weight         368.35
_chemical_name_systematic
'ethyl 4-(4-fluorophenyl)-2-(4-methoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-12-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-17 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                96.374(5)
_cell_angle_beta                 91.813(6)
_cell_angle_gamma                107.232(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0037(5)
_cell_length_b                   8.0678(4)
_cell_length_c                   16.6349(10)
_cell_measurement_reflns_used    3868
_cell_measurement_temperature    100.00(17)
_cell_measurement_theta_max      75.8160
_cell_measurement_theta_min      5.3240
_cell_volume                     890.14(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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    -54.00  33.00   1.00    1.00    --  -41.44  38.00 -90.00   87
  2  \w   -115.00 -13.00   1.00    1.00    --  -41.44 -57.00 120.00  102
  3  \w     32.00  63.00   1.00    1.00    --   41.44 -99.00  90.00   31
  4  \w    -21.00  73.00   1.00    1.00    --   41.44 -77.00   0.00   94
  5  \w     68.00 128.00   1.00    1.00    --   41.44-178.00  60.00   60
  6  \w     41.00 105.00   1.00    2.00    --  112.00 -95.00 -90.00   64
  7  \w    110.00 169.00   1.00    2.00    --  112.00  77.00-180.00   59
  8  \w     55.00  91.00   1.00    2.00    --  112.00 -45.00-120.00   36
  9  \w    110.00 139.00   1.00    2.00    --  112.00  77.00 150.00   29
 10  \w     82.00 112.00   1.00    2.00    --  112.00-126.00  60.00   30
 11  \w    142.00 176.00   1.00    2.00    --  112.00  77.00 150.00   34
 12  \w     39.00 113.00   1.00    2.00    --  112.00-126.00  30.00   74
 13  \w    138.00 168.00   1.00    2.00    --  112.00 126.00-180.00   30
 14  \w    115.00 173.00   1.00    2.00    --  112.00  77.00-150.00   58
 15  \w     40.00 112.00   1.00    2.00    --  112.00-126.00-180.00   72
 16  \w     55.00  80.00   1.00    2.00    --  112.00 -95.00 150.00   25
 17  \w     74.00 112.00   1.00    2.00    --  112.00-126.00 -90.00   38
 18  \w     85.00 178.00   1.00    2.00    --  112.00  30.00 -60.00   93
 19  \w     41.00 135.00   1.00    2.00    --  112.00 -45.00 120.00   94
 20  \w     79.00 113.00   1.00    2.00    --  112.00-126.00-120.00   34
 21  \w     45.00  70.00   1.00    2.00    --  112.00-126.00   0.00   25
 22  \w     40.00 125.00   1.00    2.00    --  112.00-142.00 158.45   85
 23  \w    -16.00  20.00   1.00    1.00    --    2.00  16.00  78.56   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0387811000
_diffrn_orient_matrix_UB_12      -0.1545585000
_diffrn_orient_matrix_UB_13      -0.0679513000
_diffrn_orient_matrix_UB_21      0.2275333000
_diffrn_orient_matrix_UB_22      0.0336214000
_diffrn_orient_matrix_UB_23      -0.0042528000
_diffrn_orient_matrix_UB_31      -0.0031605000
_diffrn_orient_matrix_UB_32      -0.1248901000
_diffrn_orient_matrix_UB_33      0.0639418000
_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  0.0504
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6796
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.488
_diffrn_reflns_theta_min         2.679
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_preparation       'slove evaporation of metanol solution'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0525
_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^+0.1565P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2891
_reflns_number_total             3509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00148b2.cif
_cod_data_source_block           176
_cod_depositor_comments
'Adding full bibliography for 7159243--7159244.cif.'
_cod_database_code               7159243
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H17 F N2 O4'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C0) = Uanis(C7)
3. Others
 Fixed Sof: H6BC(0.5) H6BD(0.5) H6AA(0.5) H6AB(0.5) C0(0.5) H0A(0.5) H0B(0.5)
 H0C(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6BC,H6BD), C6(H6AA,H6AB)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C11(H11), C18(H18), C12(H12), C9(H9), C15(H15), C19(H19),
 C8(H8)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C0(H0A,H0B,H0C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              3395
_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 3.149
_oxdiff_exptl_absorpt_empirical_full_min 0.394