A facile and concise route to (hydroxybenzoyl)pyrido[2,3-d]pyrimidine heterocycle derivatives: synthesis, and structural, spectral and computational exploration
Ashraf, Abida; Khalid, Muhammad; Tahir, Muhammad Nawaz; Yaqub, Muhammad; Naseer, Muhammad Moazzam; Kamal, Ghulam Mustafa; Saifullah, Bullo; Braga, Ataualpa Albert Carmo; Shafiq, Zahid; Rauf, Waqar; RSC Advances 9 (2019) 34567–; doi:10.1039/C9RA05415D

data_7234814
_publ_section_title
;
 A facile and concise route to (hydroxybenzoyl)pyrido[2,3-d]pyrimidine
 heterocycle derivatives: synthesis, and structural, spectral and
 computational exploration
;
_journal_issue                   59
_journal_name_full               'RSC Advances'
_journal_page_first              34567
_journal_paper_doi               10.1039/C9RA05415D
_journal_volume                  9
_journal_year                    2019
_chemical_formula_iupac          'C16 H13 N3 O4'
_chemical_formula_moiety         'C16 H13 N3 O4'
_chemical_formula_sum            'C16 H13 N3 O4'
_chemical_formula_weight         311.29
_chemical_name_systematic
;
6-(2-Hydroxy-5-methylbenzoyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-11 deposited with the CCDC.    2019-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.098(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1712(11)
_cell_length_b                   13.873(2)
_cell_length_c                   12.3934(17)
_cell_measurement_reflns_used    2477
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.927
_cell_measurement_theta_min      2.937
_cell_volume                     1404.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0.76
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9802
_diffrn_reflns_theta_full        27.927
_diffrn_reflns_theta_max         27.927
_diffrn_reflns_theta_min         2.937
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0552
_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^)+(0.1006P)^2^+0.2367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1723
_reflns_number_gt                2477
_reflns_number_total             3315
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c9ra05415d2.cif
_cod_data_source_block           MS2BZU
_cod_original_cell_volume        1403.9(3)
_cod_database_code               7234814
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              35498