Autocatalytic and DMSO-promoted regioselective synthesis of pyrimidine-fused quinolines from anilines and barbituric acids.
Yadav, Pushpendra; Chatterjee, Deblina; Bhowmick, Suman; Tiwari, Khushboo; Awasthi, Annapurna; Tiwari, Dharmendra Kumar; Chemical communications (Cambridge, England) 60 (2024) 12746–12749; doi:10.1039/d4cc04044a

data_7133934
_publ_section_title
;
 Autocatalytic and DMSO-promoted regioselective synthesis of
 pyrimidine-fused quinolines from anilines and barbituric acids.
;
_journal_issue                   87
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12746
_journal_page_last               12749
_journal_paper_doi               10.1039/d4cc04044a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C13 H11 N3 O2'
_chemical_formula_sum            'C13 H11 N3 O2'
_chemical_formula_weight         241.25
_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
_audit_creation_date             2024-03-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-05-29 deposited with the CCDC.	2024-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                81.615(13)
_cell_angle_beta                 82.031(12)
_cell_angle_gamma                80.082(14)
_cell_formula_units_Z            4
_cell_length_a                   8.252(2)
_cell_length_b                   10.694(3)
_cell_length_c                   12.745(3)
_cell_measurement_reflns_used    1504
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.38
_cell_volume                     1088.6(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1824
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4193
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.036
_diffrn_reflns_theta_min         2.377
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.6271
_exptl_absorpt_correction_T_min  0.5685
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1671 before and 0.1281 after correction.
The Ratio of minimum to maximum transmission is 0.9066.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.35(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.1079
_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^)+(0.0750P)^2^+0.7036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2378
_refine_ls_wR_factor_ref         0.2694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2392
_reflns_number_total             4193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04044a2.cif
_cod_data_source_block           tri1_a_tw
_cod_original_cell_volume        1088.5(5)
_cod_database_code               7133934
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.552(5)
 0.448(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C1(H1), C5(H5), C20(H20), C7(H7), C18(H18), C2(H2), C6(H6),
 C15(H15), C14(H14)
3.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C13(H13A,H13B,H13C), C25(H25A,H25B,H25C), C12(H12A,H12B,
 H12C)
;
_shelx_res_checksum              7195
_shelx_hkl_checksum              9935
_olex2_submission_special_instructions 'No special instructions were received'