#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:44:39 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240204.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240204
loop_
_publ_author_name
'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'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  10.00   0.50    1.64    --    0.00  77.00 150.00   78
  2  ω    -28.00  16.00   0.50    1.64    --    0.00 -37.00 -90.00   88
  3  ω    -20.00   5.00   0.50    1.64    --    0.00 -37.00-120.00   50
  4  ω    -69.00  18.00   0.50    1.64    --    0.00 -37.00-180.00  174
  5  ω    -21.00   4.00   0.50    1.64    --    0.00  77.00-120.00   50
  6  ω     44.00  70.00   0.50    6.56    --  107.20 -82.00 150.00   52
  7  ω     35.00 140.00   0.50    6.56    --  107.20 -82.00-180.00  210
  8  ω     19.00 130.00   0.50    6.56    --  107.20 -61.00-180.00  222
  9  ω     81.00 120.00   0.50    6.56    --  107.20 -82.00  90.00   78
 10  ω     27.00  56.00   0.50    6.56    --  107.20 -77.00-150.00   58
 11  ω     95.00 170.00   0.50    6.56    --  107.20  30.00 -30.00  150
 12  ω     20.00  99.00   0.50    6.56    --  107.20 -15.00-180.00  158
 13  ω    158.00 197.00   0.50    6.56    --  107.20  45.00 150.00   78
 14  ω     86.00 111.00   0.50    6.56    --  107.20 -82.00 150.00   50
 15  ω     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       'ω 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/[σ²(Fo²)+(0.0521P)²+1.0885P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N5 N 0.26398(4) 0.50914(18) 0.98023(11) 0.0174(2) Uani 1 1 d . . . . .
O1 O 0.12424(3) 0.09220(16) 1.33863(10) 0.0227(2) Uani 1 1 d . . . . .
N4 N 0.22699(4) 0.32049(19) 1.13809(12) 0.0209(2) Uani 1 1 d . . . . .
C9 C 0.23118(4) 0.5122(2) 1.06458(12) 0.0163(3) Uani 1 1 d . . . . .
N1 N 0.03715(4) 0.16464(19) 1.62476(12) 0.0213(2) Uani 1 1 d . . . . .
C5 C 0.11678(4) 0.2890(2) 1.37507(13) 0.0175(3) Uani 1 1 d . . . . .
N3 N 0.13512(3) 0.48176(19) 1.33046(11) 0.0183(2) Uani 1 1 d . . . . .
H3 H 0.126638 0.614058 1.361944 0.022 Uiso 1 1 calc R . . . .
C6 C 0.16688(4) 0.4895(2) 1.23717(13) 0.0172(3) Uani 1 1 d . . . . .
N2 N 0.07631(4) 0.54665(19) 1.51261(12) 0.0194(2) Uani 1 1 d . . . . .
C7 C 0.17113(4) 0.6891(2) 1.16128(13) 0.0183(3) Uani 1 1 d . . . . .
H7 H 0.151978 0.815455 1.169061 0.022 Uiso 1 1 calc R . . . .
C2 C 0.02917(4) 0.3805(2) 1.66126(14) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.009595 0.405905 1.727358 0.025 Uiso 1 1 calc R . . . .
C11 C 0.27519(4) 0.7151(2) 0.90628(13) 0.0184(3) Uani 1 1 d . . . . .
H11A H 0.296388 0.809773 0.964912 0.022 Uiso 1 1 calc R . . . .
H11B H 0.248616 0.808653 0.881486 0.022 Uiso 1 1 calc R . . . .
C8 C 0.20321(4) 0.7025(2) 1.07495(13) 0.0177(3) Uani 1 1 d . . . . .
H8 H 0.206453 0.837866 1.023206 0.021 Uiso 1 1 calc R . . . .
C4 C 0.08484(4) 0.3303(2) 1.47691(13) 0.0171(3) Uani 1 1 d . . . . .
N6 N 0.33255(4) 0.49318(19) 0.81133(12) 0.0205(2) Uani 1 1 d . . . . .
C3 C 0.04848(4) 0.5691(2) 1.60597(14) 0.0215(3) Uani 1 1 d . . . . .
H3A H 0.041688 0.719107 1.635504 0.026 Uiso 1 1 calc R . . . .
C10 C 0.19591(4) 0.3110(2) 1.22224(14) 0.0210(3) Uani 1 1 d . . . . .
H10 H 0.193608 0.175201 1.274382 0.025 Uiso 1 1 calc R . . . .
C1 C 0.06531(4) 0.1420(2) 1.53166(14) 0.0207(3) Uani 1 1 d . . . . .
H1 H 0.072123 -0.008054 1.502216 0.025 Uiso 1 1 calc R . . . .
C13 C 0.32201(5) 0.2878(2) 0.88819(14) 0.0232(3) Uani 1 1 d . . . . .
H13A H 0.348967 0.197931 0.914427 0.028 Uiso 1 1 calc R . . . .
H13B H 0.301341 0.188951 0.830408 0.028 Uiso 1 1 calc R . . . .
C12 C 0.29495(4) 0.6451(2) 0.77857(13) 0.0189(3) Uani 1 1 d . . . . .
H12A H 0.272587 0.565096 0.715824 0.023 Uiso 1 1 calc R . . . .
H12B H 0.304273 0.784511 0.732056 0.023 Uiso 1 1 calc R . . . .
C14 C 0.30191(5) 0.3576(2) 1.01367(14) 0.0224(3) Uani 1 1 d . . . . .
H14A H 0.292624 0.218158 1.060219 0.027 Uiso 1 1 calc R . . . .
H14B H 0.324046 0.438462 1.076775 0.027 Uiso 1 1 calc R . . . .
C16 C 0.40564(5) 0.3567(3) 0.78208(17) 0.0320(4) Uani 1 1 d . . . . .
O2A O 0.36639(6) 0.6319(3) 0.63565(19) 0.0337(4) Uani 0.66 1 d . . P A 3
C15A C 0.36595(13) 0.5028(7) 0.7328(3) 0.0213(7) Uani 0.66 1 d . . P A 3
C18 C 0.47349(6) 0.0826(3) 0.84207(17) 0.0388(4) Uani 1 1 d . . . . .
H18 H 0.495752 -0.027888 0.866235 0.047 Uiso 1 1 calc R . . B 2
C19A C 0.44396(14) 0.4191(9) 0.8775(4) 0.0413(10) Uani 0.6 1 d . . P A 1
H19A H 0.444894 0.565146 0.920943 0.050 Uiso 0.6 1 calc R . P A 1
N8A N 0.47733(14) 0.2743(10) 0.9040(5) 0.0478(11) Uani 0.6 1 d . . P A 1
N7A N 0.40252(9) 0.1607(5) 0.7283(4) 0.0448(7) Uani 0.6 1 d . . P A 1
C17A C 0.43616(11) 0.0154(6) 0.7527(4) 0.0382(7) Uani 0.6 1 d . . P A 1
H17A H 0.435166 -0.131759 0.710644 0.046 Uiso 0.6 1 calc R . P A 1
N7B N 0.41694(13) 0.2128(7) 0.6780(4) 0.0301(8) Uani 0.4 1 d . . P A 2
N8B N 0.46267(19) 0.2424(12) 0.9359(6) 0.0379(12) Uani 0.4 1 d . . P A 2
C17B C 0.45232(18) 0.0854(9) 0.7174(5) 0.0385(10) Uani 0.4 1 d . . P A 2
H17B H 0.463166 -0.010512 0.651145 0.046 Uiso 0.4 1 calc R . P A 2
C19B C 0.4270(2) 0.3699(11) 0.8976(7) 0.0364(13) Uani 0.4 1 d . . P A 2
H19B H 0.417411 0.475477 0.961270 0.044 Uiso 0.4 1 calc R . P A 2
C15B C 0.3718(2) 0.5514(14) 0.7783(7) 0.0276(15) Uani 0.34 1 d . . P A 4
O2B O 0.37922(13) 0.7372(9) 0.7262(7) 0.0699(18) Uani 0.34 1 d . . P A 4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N5 C11 121.45(10) . . ?
C9 N5 C14 119.20(10) . . ?
C11 N5 C14 112.07(10) . . ?
C10 N4 C9 119.33(11) . . ?
N5 C9 C8 123.17(11) . . ?
N4 C9 N5 115.99(11) . . ?
N4 C9 C8 120.84(11) . . ?
C2 N1 C1 115.53(11) . . ?
O1 C5 N3 125.22(12) . . ?
O1 C5 C4 120.19(11) . . ?
N3 C5 C4 114.59(11) . . ?
C5 N3 C6 125.68(11) . . ?
C7 C6 N3 119.34(11) . . ?
C10 C6 N3 123.00(12) . . ?
C10 C6 C7 117.57(12) . . ?
C3 N2 C4 115.74(11) . . ?
C8 C7 C6 119.84(12) . . ?
N1 C2 C3 122.29(12) . . ?
N5 C11 C12 109.69(10) . . ?
C7 C8 C9 119.08(12) . . ?
N2 C4 C5 119.23(11) . . ?
N2 C4 C1 122.01(12) . . ?
C1 C4 C5 118.75(11) . . ?
C12 N6 C13 112.89(11) . . ?
C15A N6 C13 123.69(19) . . ?
C15A N6 C12 118.66(19) . . ?
C15B N6 C13 126.3(4) . . ?
C15B N6 C12 120.7(4) . . ?
N2 C3 C2 122.18(12) . . ?
N4 C10 C6 123.34(12) . . ?
N1 C1 C4 122.23(12) . . ?
N6 C13 C14 110.10(11) . . ?
N6 C12 C11 110.97(10) . . ?
N5 C14 C13 111.45(11) . . ?
N7A C16 C19A 120.9(3) . . ?
C19B C16 N7B 124.0(3) . . ?
N6 C15A C16 115.2(3) . . ?
O2A C15A N6 123.5(3) . . ?
O2A C15A C16 121.0(3) . . ?
N8A C18 C17A 124.4(3) . . ?
C17B C18 N8B 119.1(4) . . ?
N8A C19A C16 121.1(4) . . ?
C18 N8A C19A 115.5(4) . . ?
C16 N7A C17A 118.4(3) . . ?
N7A C17A C18 119.6(3) . . ?
C17B N7B C16 112.1(3) . . ?
C19B N8B C18 115.6(5) . . ?
C18 C17B N7B 125.1(4) . . ?
C16 C19B N8B 123.4(6) . . ?
N6 C15B C16 116.1(5) . . ?
O2B C15B N6 122.8(7) . . ?
O2B C15B C16 120.0(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N5 C9 1.3814(16) . ?
N5 C11 1.4644(16) . ?
N5 C14 1.4703(16) . ?
O1 C5 1.2285(16) . ?
N4 C9 1.3444(16) . ?
N4 C10 1.3392(17) . ?
C9 C8 1.4123(17) . ?
N1 C2 1.3356(17) . ?
N1 C1 1.3416(17) . ?
C5 N3 1.3504(16) . ?
C5 C4 1.5052(17) . ?
N3 C6 1.4198(16) . ?
C6 C7 1.3960(18) . ?
C6 C10 1.3877(18) . ?
N2 C4 1.3398(16) . ?
N2 C3 1.3359(17) . ?
C7 C8 1.3795(18) . ?
C2 C3 1.3882(19) . ?
C11 C12 1.5193(17) . ?
C4 C1 1.3875(18) . ?
N6 C13 1.4712(17) . ?
N6 C12 1.4630(16) . ?
N6 C15A 1.358(4) . ?
N6 C15B 1.332(8) . ?
C13 C14 1.5051(18) . ?
C16 C15A 1.522(4) . ?
C16 C19A 1.472(5) . ?
C16 N7A 1.256(4) . ?
C16 N7B 1.401(4) . ?
C16 C19B 1.256(7) . ?
C16 C15B 1.534(8) . ?
O2A C15A 1.222(4) . ?
C18 N8A 1.270(6) . ?
C18 C17A 1.424(4) . ?
C18 N8B 1.381(7) . ?
C18 C17B 1.330(5) . ?
C19A N8A 1.331(7) . ?
N7A C17A 1.337(4) . ?
N7B C17B 1.338(6) . ?
N8B C19B 1.343(9) . ?
C15B O2B 1.229(9) . ?
