Design, synthesis, and anti-mycobacterial evaluation of 1,8-naphthyridine-3-carbonitrile analogues
Khetmalis, Yogesh Mahadu; Shobha, Singarapalle; Nandikolla, Adinarayana; Chandu, Ala; Murugesan, Sankaranarayanan; Kumar, Muthyala Murali Krishna; Chandra Sekhar, Kondapalli Venkata Gowri; RSC Advances 14 (2024) 22676–22689; doi:10.1039/D4RA04262J

data_7249072
_publ_section_title
;
 Design, synthesis, and anti-mycobacterial evaluation of
 1,8-naphthyridine-3-carbonitrile analogues
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              22676
_journal_page_last               22689
_journal_paper_doi               10.1039/D4RA04262J
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C21 H19 F N6 O'
_chemical_formula_sum            'C21 H19 F N6 O'
_chemical_formula_weight         390.42
_chemical_name_systematic        ANC-5
_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     dual
_audit_creation_date             2024-03-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-03-22 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                85.352(2)
_cell_angle_beta                 88.350(2)
_cell_angle_gamma                73.647(2)
_cell_formula_units_Z            2
_cell_length_a                   6.03380(10)
_cell_length_b                   7.3549(2)
_cell_length_c                   20.9236(5)
_cell_measurement_reflns_used    5473
_cell_measurement_temperature    126
_cell_measurement_theta_max      79.3530
_cell_measurement_theta_min      4.2280
_cell_volume                     888.04(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      126
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_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    -77.00 -19.00   0.50    0.75    --    0.00 -37.00  60.00  116
  2  \w    -57.00 -27.00   0.50    0.75    --    0.00 -37.00 120.00   60
  3  \w    -21.00  14.00   0.50    0.75    --    0.00 -37.00 120.00   70
  4  \w    -18.00  42.00   0.50    0.75    --    0.00  37.00  30.00  120
  5  \w     46.00  87.00   0.50    0.75    --    0.00  37.00  30.00   82
  6  \w      4.00  29.00   0.50    0.75    --    0.00 -77.00-180.00   50
  7  \w     89.00 115.00   0.50    2.50    --  107.20 -82.00 -30.00   52
  8  \w     26.00 139.00   0.50    2.50    --  107.20 -82.00-120.00  226
  9  \w     18.00 113.00   0.50    2.50    --  107.20 -61.00 120.00  190
 10  \w     29.00  55.00   0.50    2.50    --  107.20 -82.00  60.00   52
 11  \w     96.00 136.00   0.50    2.50    --  107.20 -82.00-180.00   80
 12  \w    113.00 194.00   0.50    2.50    --  107.20  30.00 -30.00  162
 13  \w     29.00 119.00   0.50    2.50    --  107.20 -30.00-120.00  180
 14  \w     21.00 111.00   0.50    2.50    --  107.20 -45.00-150.00  180
 15  \w     19.00 118.00   0.50    2.50    --  107.20 -45.00   0.00  198
 16  \w    107.00 134.00   0.50    2.50    --  107.20 -82.00  30.00   54
 17  \w     28.00  95.00   0.50    2.50    --  107.20 -82.00  30.00  134
 18  \w     86.00 137.00   0.50    2.50    --  107.20 -82.00 -90.00  102
 19  \w     80.00 105.00   0.50    2.50    --  107.20 -82.00-150.00   50
 20  \w    108.00 134.00   0.50    2.50    --  107.20 -82.00   0.00   52
 21  \w     23.00 112.00   0.50    2.50    --  107.20 -82.00 120.00  178
 22  \w     85.00 110.00   0.50    2.50    --  107.20 -82.00  60.00   50
 23  \w     56.00 170.00   0.50    2.50    --  107.20   0.00  90.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0740267000
_diffrn_orient_matrix_UB_12      -0.1892595000
_diffrn_orient_matrix_UB_13      0.0416823000
_diffrn_orient_matrix_UB_21      -0.0197998000
_diffrn_orient_matrix_UB_22      0.1100423000
_diffrn_orient_matrix_UB_23      0.0604766000
_diffrn_orient_matrix_UB_31      -0.2548206000
_diffrn_orient_matrix_UB_32      0.0005391000
_diffrn_orient_matrix_UB_33      0.0078926000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9099
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.758
_diffrn_reflns_theta_min         4.240
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_preparation       '10% MeOH in DCM'
_exptl_crystal_recrystallization_method Cu
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0625P)^2^+0.3180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3350
_reflns_number_total             3744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra04262j2.cif
_cod_data_source_block           ANC-5
_cod_database_code               7249072
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.920
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C1(H1), C2(H2), C3(H3), C6(H6A), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              79574
_olex2_submission_original_sample_id NCF
_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 2.095
_oxdiff_exptl_absorpt_empirical_full_min 0.754