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_7240206
_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 Cl N6 O2'
_chemical_formula_sum            'C21 H19 Cl N6 O2'
_chemical_formula_weight         422.88
_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_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-24
_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                90
_cell_angle_beta                 98.5610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.69780(10)
_cell_length_b                   21.2347(3)
_cell_length_c                   16.1672(2)
_cell_measurement_reflns_used    6773
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.2780
_cell_measurement_theta_min      4.1530
_cell_volume                     1934.29(5)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9957
_diffrn_measured_fraction_theta_max 0.9475
_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    -89.00  23.00   0.50    1.89    --    0.00 -57.00 150.00  224
  2  \w    -20.00  11.00   0.50    1.89    --    0.00 -37.00   0.00   62
  3  \w    -28.00  51.00   0.50    1.89    --    0.00  77.00 120.00  158
  4  \w     18.00 129.00   0.50    7.56    --  107.20 -61.00  30.00  222
  5  \w     31.00 135.00   0.50    7.56    --  107.20 -15.00 120.00  208
  6  \w     51.00 134.00   0.50    7.56    --  107.20 -82.00  30.00  166
  7  \w     64.00 125.00   0.50    7.56    --  107.20 -82.00-120.00  122
  8  \w     93.00 140.00   0.50    7.56    --  107.20  82.00 120.00   94
  9  \w    144.00 191.00   0.50    7.56    --  107.20  82.00 120.00   94
 10  \w     90.00 115.00   0.50    7.56    --  107.20 -30.00 -90.00   50
 11  \w     88.00 124.00   0.50    7.56    --  107.20  45.00  30.00   72
 12  \w     22.00  67.00   0.50    7.56    --  107.20 -30.00 -90.00   90
;
_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      0.0669101000
_diffrn_orient_matrix_UB_12      0.0314827000
_diffrn_orient_matrix_UB_13      0.0860704000
_diffrn_orient_matrix_UB_21      -0.0299390000
_diffrn_orient_matrix_UB_22      0.0653780000
_diffrn_orient_matrix_UB_23      -0.0416023000
_diffrn_orient_matrix_UB_31      -0.2634930000
_diffrn_orient_matrix_UB_32      0.0005367000
_diffrn_orient_matrix_UB_33      0.0117170000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10531
_diffrn_reflns_theta_full        67.0000
_diffrn_reflns_theta_max         80.24
_diffrn_reflns_theta_min         4.16
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74232
_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    1.4520
_exptl_crystal_description       plate
_exptl_crystal_F_000             884.0949
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.2606
_refine_diff_density_min         -0.4266
_refine_diff_density_rms         0.0613
_refine_ls_d_res_high            0.7822
_refine_ls_d_res_low             10.6173
_refine_ls_goodness_of_fit_ref   1.0284
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0284
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+1.0211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -5
_reflns_number_gt                3669
_reflns_number_total             4009
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0ra01348j2.cif
_cod_data_source_block           KVGCS_P-9
_cod_depositor_comments
'Adding full bibliography for 7240204--7240206.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7240206
_reflns_odcompleteness_completeness 98.85
_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:
 C8(H8a,H8b), C9(H9a,H9b), C6(H6a,H6b), C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C1(H1), C2(H2), C17(H17), C18(H18), C11(H11), C3(H3), C13(H13),
 C14(H14), C21(H21), C20(H20)
;
_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 1.776
_oxdiff_exptl_absorpt_empirical_full_min 0.641