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_7240204
_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         'C19 H18 N8 O2'
_chemical_formula_sum            'C19 H18 N8 O2'
_chemical_formula_weight         390.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                 96.4675(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.7919(5)
_cell_length_b                   5.80932(8)
_cell_length_c                   9.90381(15)
_cell_measurement_reflns_used    5983
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.3370
_cell_measurement_theta_min      5.7990
_cell_volume                     1760.32(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_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    -29.00  10.00   0.50    1.64    --    0.00  77.00 150.00   78
  2  \w    -28.00  16.00   0.50    1.64    --    0.00 -37.00 -90.00   88
  3  \w    -20.00   5.00   0.50    1.64    --    0.00 -37.00-120.00   50
  4  \w    -69.00  18.00   0.50    1.64    --    0.00 -37.00-180.00  174
  5  \w    -21.00   4.00   0.50    1.64    --    0.00  77.00-120.00   50
  6  \w     44.00  70.00   0.50    6.56    --  107.20 -82.00 150.00   52
  7  \w     35.00 140.00   0.50    6.56    --  107.20 -82.00-180.00  210
  8  \w     19.00 130.00   0.50    6.56    --  107.20 -61.00-180.00  222
  9  \w     81.00 120.00   0.50    6.56    --  107.20 -82.00  90.00   78
 10  \w     27.00  56.00   0.50    6.56    --  107.20 -77.00-150.00   58
 11  \w     95.00 170.00   0.50    6.56    --  107.20  30.00 -30.00  150
 12  \w     20.00  99.00   0.50    6.56    --  107.20 -15.00-180.00  158
 13  \w    158.00 197.00   0.50    6.56    --  107.20  45.00 150.00   78
 14  \w     86.00 111.00   0.50    6.56    --  107.20 -82.00 150.00   50
 15  \w     87.00 142.00   0.50    6.56    --  107.20  45.00 150.00  110
;
_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      -0.0480496000
_diffrn_orient_matrix_UB_12      -0.0259397000
_diffrn_orient_matrix_UB_13      -0.0606520000
_diffrn_orient_matrix_UB_21      -0.0141578000
_diffrn_orient_matrix_UB_22      -0.0056868000
_diffrn_orient_matrix_UB_23      0.1442598000
_diffrn_orient_matrix_UB_31      -0.0050434000
_diffrn_orient_matrix_UB_32      0.2639391000
_diffrn_orient_matrix_UB_33      -0.0028537000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9609
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.603
_diffrn_reflns_theta_min         4.335
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80136
_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            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0521P)^2^+1.0885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3424
_reflns_number_total             3735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra01348j2.cif
_cod_data_source_block           KVGCS_P2
_cod_depositor_comments
'Adding full bibliography for 7240204--7240206.cif.'
_cod_database_code               7240204
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.849
_reflns_odcompleteness_completeness 99.53
_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. Others
 Fixed Sof: O2A(0.66) C15A(0.66) C19A(0.6) H19A(0.6) N8A(0.6) N7A(0.6)
 C17A(0.6) H17A(0.6) N7B(0.4) N8B(0.4) C17B(0.4) H17B(0.4) C19B(0.4) H19B(0.4)
 C15B(0.34) O2B(0.34)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C2(H2), C8(H8), C3(H3A), C10(H10), C1(H1), C18(H18),
 C19A(H19A), C17A(H17A), C17B(H17B), C19B(H19B)
;
_shelx_res_checksum              66833
_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 1.519
_oxdiff_exptl_absorpt_empirical_full_min 0.627