Seeking potent anti-tubercular agents: design and synthesis of substituted-N-(6-(4-(pyrazine-2-carbonyl)piperazine/homopiperazine-1-yl)pyridin-3-yl)benzamide derivatives as anti-tubercular agents
Srinivasarao, Singireddi; Nandikolla, Adinarayana; Suresh, Amaroju; Calster, Kevin Van; De Voogt, Linda; Cappoen, Davie; Ghosh, Balaram; Aggarwal, Himanshu; Murugesan, Sankaranarayanan; Chandra Sekhar, Kondapalli Venkata Gowri; RSC Advances 10 (2020) 12272–12288; doi:10.1039/D0RA01348J

data_7240205
_publ_section_title
;
 Seeking potent anti-tubercular agents: design and synthesis of
 substituted-N-(6-(4-(pyrazine-2-carbonyl)piperazine/homopiperazine-1-yl)pyridin-3-yl)benzamide
 derivatives as anti-tubercular agents
;
_journal_issue                   21
_journal_name_full               'RSC Advances'
_journal_page_first              12272
_journal_page_last               12288
_journal_paper_doi               10.1039/D0RA01348J
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C21 H19 N7 O4'
_chemical_formula_sum            'C21 H19 N7 O4'
_chemical_formula_weight         433.43
_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             2020-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-25 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                74.307(2)
_cell_angle_beta                 74.059(2)
_cell_angle_gamma                79.348(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2628(2)
_cell_length_b                   9.9451(2)
_cell_length_c                   12.8729(3)
_cell_measurement_reflns_used    7520
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.0690
_cell_measurement_theta_min      4.6430
_cell_volume                     972.22(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_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    -21.00  26.00   0.50    2.50    --    0.00  57.00 150.00   94
  2  \w    -56.00  -9.00   0.50    2.50    --    0.00 -37.00-120.00   94
  3  \w    -88.00  23.00   0.50    2.50    --    0.00 -57.00  90.00  222
  4  \w    -42.00  19.00   0.50    2.50    --    0.00 -37.00 -30.00  122
  5  \w    -83.00 -57.00   0.50    2.50    --    0.00 -37.00-120.00   52
  6  \w    157.00 190.00   0.50    5.45    --  107.20  30.00 -30.00   66
  7  \w    109.00 151.00   0.50    5.45    --  107.20  30.00 -30.00   84
  8  \w     92.00 197.00   0.50    5.45    --  107.20  30.00  30.00  210
  9  \w     37.00 140.00   0.50    5.45    --  107.20 -82.00 -90.00  206
 10  \w     28.00 108.00   0.50    5.45    --  107.20 -61.00 -90.00  160
 11  \w     98.00 124.00   0.50    5.45    --  107.20  30.00  60.00   52
 12  \w    126.00 197.00   0.50    5.45    --  107.20  30.00  60.00  142
 13  \w     18.00 127.00   0.50    5.45    --  107.20 -61.00 120.00  218
 14  \w     18.00  66.00   0.50    5.45    --  107.20 -15.00  60.00   96
 15  \w     23.00  66.00   0.50    5.45    --  107.20 -82.00-180.00   86
 16  \w     85.00 110.00   0.50    5.45    --  107.20 -82.00  60.00   50
 17  \w     30.00  67.00   0.50    5.45    --  107.20 -82.00  60.00   74
 18  \w     90.00 118.00   0.50    5.45    --  107.20 -82.00-180.00   56
 19  \w     20.00 139.00   0.50    5.45    --  107.20 -82.00 120.00  238
 20  \w     88.00 138.00   0.50    5.45    --  107.20 -82.00 -30.00  100
 21  \w     89.00 194.00   0.50    5.45    --  107.20  30.00   0.00  210
 22  \w     33.00  64.00   0.50    5.45    --  107.20 -61.00  60.00   62
 23  \w     97.00 123.00   0.50    5.45    --  107.20 -82.00  90.00   52
 24  \w     89.00 114.00   0.50    5.45    --  107.20 -45.00-150.00   50
;
_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      0.0545295000
_diffrn_orient_matrix_UB_12      -0.0017137000
_diffrn_orient_matrix_UB_13      -0.1241374000
_diffrn_orient_matrix_UB_21      0.0285826000
_diffrn_orient_matrix_UB_22      0.1559825000
_diffrn_orient_matrix_UB_23      -0.0297168000
_diffrn_orient_matrix_UB_31      0.1853427000
_diffrn_orient_matrix_UB_32      -0.0439451000
_diffrn_orient_matrix_UB_33      0.0090877000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10168
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.430
_diffrn_reflns_theta_min         4.652
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78388
_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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0515P)^2^+0.3144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.0996
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3812
_reflns_number_total             4089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra01348j2.cif
_cod_data_source_block           KVGCS_P5
_cod_depositor_comments
'Adding full bibliography for 7240204--7240206.cif.'
_cod_database_code               7240205
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.893
_reflns_odcompleteness_completeness 99.40
_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:
 C7(H7A,H7B), C8(H8A,H8B), C6(H6A,H6B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C21(H21), C14(H14), C12(H12), C11(H11), C17(H17), C1(H1), C2(H2),
 C19(H19), C18(H18), C3(H3)
;
_shelx_res_checksum              70801
_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 1.675
_oxdiff_exptl_absorpt_empirical_full_min 0.691