#------------------------------------------------------------------------------
#$Date: 2022-11-09 05:05:03 +0200 (Wed, 09 Nov 2022) $
#$Revision: 279134 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/42/2244212.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244212
loop_
_publ_author_name
'Richter, Adrian'
'Goddard, Richard'
'Schönefeld, Roy'
'Imming, Peter'
'Seidel, Rüdiger W.'
_publ_section_title
;
 Structural characterization and antimycobacterial evaluation of a
 benzimidazole analogue of the antituberculosis clinical drug candidate
 TBA-7371
;
_journal_coeditor_code           VM2273
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022010556
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C17 H18 F N5 O2'
_chemical_formula_moiety         'C17 H18 F N5 O2'
_chemical_formula_sum            'C17 H18 F N5 O2'
_chemical_formula_weight         343.363
_chemical_name_common
N-(2-fluoroethyl)-1-[(6-methoxy-5-methylpyrimidin-4-yl)methyl]-1H-benzo[d]imidazole-4-carboxamide
_chemical_name_systematic
N-(2-Fluoroethyl)-1-[(6-methoxy-5-methylpyrimidin-4-yl)methyl]-1,3-benzodiazole-4-carboxamide
_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
_atom_sites_solution_secondary   difmap
_audit_block_code                GOD-GB-143_AR367-2_Heptan_TCM_Imus_100K
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                71.040(4)
_cell_angle_beta                 77.874(5)
_cell_angle_gamma                87.780(4)
_cell_formula_units_Z            4
_cell_length_a                   7.6940(19)
_cell_length_b                   15.013(4)
_cell_length_c                   15.281(4)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2227
_cell_measurement_theta_min      2.7091
_cell_volume                     1631.3(7)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2018) and MERCURY (Macrae et al.,
2020)
;
_computing_publication_material
;
enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
olex2.refine (Bourhis et al.,  2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9867
_diffrn_measurement_device_type  'Bruker AXS Kappa Mach3 APEX II'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         'Incoatec I\mS'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            58016
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         1.43
_diffrn_source                   'microfocus X-ray source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.99859
_exptl_absorpt_correction_T_min  0.99380
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.099
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.3359
_refine_diff_density_min         -0.3159
_refine_ls_goodness_of_fit_ref   1.0703
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     595
_refine_ls_number_reflns         8147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0703
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0302P)²+0.1357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                6141
_reflns_number_total             8147
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            vm2273sup1.cif
_cod_data_source_block           I
_cod_database_code               2244212
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_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
C C2_1 0.24678(14) 0.11875(7) 0.50249(7) 0.0171(2) Uani 1.000000
H H2_1 0.1399(16) 0.1169(8) 0.4698(8) 0.033(3) Uiso 1.000000
C C3A_1 0.40214(12) 0.12795(6) 0.60043(7) 0.01224(19) Uani 1.000000
C C4_1 0.46666(13) 0.12885(6) 0.67969(7) 0.0138(2) Uani 1.000000
C C5_1 0.64993(14) 0.12841(7) 0.67153(8) 0.0188(2) Uani 1.000000
H H5_1 0.7017(16) 0.1288(9) 0.7320(9) 0.037(3) Uiso 1.000000
C C6_1 0.76757(14) 0.12644(8) 0.58895(8) 0.0223(2) Uani 1.000000
H H6_1 0.9064(17) 0.1261(8) 0.5876(9) 0.040(3) Uiso 1.000000
C C7_1 0.70606(13) 0.12396(7) 0.51032(8) 0.0187(2) Uani 1.000000
H H7_1 0.7946(16) 0.1207(8) 0.4507(9) 0.038(3) Uiso 1.000000
C C7A_1 0.52267(12) 0.12461(6) 0.51864(7) 0.0131(2) Uani 1.000000
C C8_1 0.35297(14) 0.12221(7) 0.77376(7) 0.0175(2) Uani 1.000000
C C9_1 0.05871(17) 0.09121(8) 0.87354(8) 0.0265(3) Uani 1.000000
H H9a_1 0.1274(19) 0.0422(11) 0.9242(10) 0.057(4) Uiso 1.000000
H H9b_1 -0.0673(19) 0.0628(10) 0.8694(10) 0.050(4) Uiso 1.000000
C C10_1 0.01296(17) 0.17191(8) 0.91114(8) 0.0258(3) Uani 1.000000
H H10a_1 -0.0661(19) 0.1461(10) 0.9831(11) 0.057(4) Uiso 1.000000
H H10b_1 0.1311(18) 0.2145(9) 0.9030(9) 0.047(4) Uiso 1.000000
C C11_1 0.48068(16) 0.10678(7) 0.36547(7) 0.0188(2) Uani 1.000000
H H11a_1 0.3719(18) 0.0773(9) 0.3485(9) 0.044(4) Uiso 1.000000
H H11b_1 0.5883(18) 0.0590(9) 0.3682(9) 0.048(4) Uiso 1.000000
C C12_1 0.54232(13) 0.19816(6) 0.28726(7) 0.01278(19) Uani 1.000000
C C13_1 0.66938(12) 0.19801(6) 0.20828(7) 0.01218(19) Uani 1.000000
C C14_1 0.70948(12) 0.28746(6) 0.13868(6) 0.01223(19) Uani 1.000000
C C15_1 0.51185(13) 0.35548(7) 0.22720(7) 0.0151(2) Uani 1.000000
H H15_1 0.4475(15) 0.4202(8) 0.2342(8) 0.031(3) Uiso 1.000000
C C16_1 0.75853(15) 0.11175(7) 0.19506(8) 0.0172(2) Uani 1.000000
H H16a_1 0.8798(19) 0.1290(10) 0.1421(10) 0.054(4) Uiso 1.000000
H H16b_1 0.8024(18) 0.0689(10) 0.2556(10) 0.052(4) Uiso 1.000000
H H16c_1 0.677(2) 0.0719(11) 0.1756(10) 0.061(4) Uiso 1.000000
C C17_1 0.88043(14) 0.38333(7) -0.00710(7) 0.0181(2) Uani 1.000000
H H17a_1 0.9829(17) 0.3724(8) -0.0611(9) 0.040(3) Uiso 1.000000
H H17b_1 0.7668(16) 0.4161(8) -0.0362(8) 0.033(3) Uiso 1.000000
H H17c_1 0.9341(16) 0.4290(9) 0.0248(9) 0.037(3) Uiso 1.000000
N N1_1 0.41820(11) 0.11800(5) 0.45741(5) 0.01466(17) Uani 1.000000
N N2_1 0.17564(12) 0.11793(6) 0.78099(6) 0.0202(2) Uani 1.000000
H H2a_1 0.1293(17) 0.1211(9) 0.7235(10) 0.036(4) Uiso 1.000000
N N3_1 0.22925(10) 0.12443(6) 0.58814(6) 0.01580(18) Uani 1.000000
N N4_1 0.46198(11) 0.27632(6) 0.29767(6) 0.01515(18) Uani 1.000000
N N5_1 0.63354(10) 0.36553(5) 0.14786(6) 0.01407(17) Uani 1.000000
O O1_1 0.41907(11) 0.11614(5) 0.84196(5) 0.02732(19) Uani 1.000000
O O2_1 0.83091(9) 0.29152(5) 0.06084(5) 0.01625(15) Uani 1.000000
F F1_1 -0.09275(9) 0.23342(5) 0.85713(5) 0.0407(2) Uani 1.000000
C C2_2 0.63497(13) 0.58977(7) 0.02129(7) 0.0161(2) Uani 1.000000
H H2_2 0.6202(16) 0.5177(9) 0.0635(9) 0.038(3) Uiso 1.000000
C C3A_2 0.71862(12) 0.72002(6) -0.08890(7) 0.01256(19) Uani 1.000000
C C4_2 0.79584(12) 0.79156(7) -0.17228(7) 0.0130(2) Uani 1.000000
C C5_2 0.75312(13) 0.88396(7) -0.17785(7) 0.0161(2) Uani 1.000000
H H5_2 0.8156(16) 0.9408(9) -0.2421(9) 0.035(3) Uiso 1.000000
C C6_2 0.63746(14) 0.90545(7) -0.10381(7) 0.0188(2) Uani 1.000000
H H6_2 0.6057(16) 0.9770(9) -0.1100(8) 0.036(3) Uiso 1.000000
C C7_2 0.55929(14) 0.83519(7) -0.02112(7) 0.0171(2) Uani 1.000000
H H7_2 0.4735(16) 0.8528(8) 0.0344(8) 0.034(3) Uiso 1.000000
C C7A_2 0.60227(12) 0.74284(7) -0.01578(7) 0.0140(2) Uani 1.000000
C C8_2 0.91827(12) 0.77332(7) -0.25397(7) 0.0138(2) Uani 1.000000
C C9_2 1.08197(14) 0.65409(8) -0.31197(8) 0.0188(2) Uani 1.000000
H H9a_2 1.1513(16) 0.5933(9) -0.2806(9) 0.039(3) Uiso 1.000000
H H9b_2 1.1762(16) 0.7109(9) -0.3576(9) 0.035(3) Uiso 1.000000
C C10_2 0.97648(16) 0.62865(9) -0.37364(8) 0.0269(3) Uani 1.000000
H H10a_2 0.8958(17) 0.6864(9) -0.4029(9) 0.044(3) Uiso 1.000000
H H10b_2 1.0606(18) 0.6044(9) -0.4256(10) 0.054(4) Uiso 1.000000
C C11_2 0.43832(14) 0.64282(8) 0.14634(7) 0.0192(2) Uani 1.000000
H H11a_2 0.3521(16) 0.5797(9) 0.1648(9) 0.039(3) Uiso 1.000000
H H11b_2 0.3542(16) 0.7039(9) 0.1409(9) 0.038(3) Uiso 1.000000
C C12_2 0.54170(13) 0.63169(7) 0.22336(7) 0.0154(2) Uani 1.000000
C C13_2 0.45344(13) 0.63352(7) 0.31175(7) 0.0161(2) Uani 1.000000
C C14_2 0.56317(15) 0.62089(7) 0.37788(7) 0.0201(2) Uani 1.000000
C C15_2 0.80399(15) 0.60741(8) 0.27110(8) 0.0257(3) Uani 1.000000
H H15_2 0.9430(17) 0.5958(9) 0.2557(9) 0.043(3) Uiso 1.000000
C C16_2 0.25762(15) 0.64610(8) 0.33854(8) 0.0215(2) Uani 1.000000
H H16a_2 0.2278(19) 0.6794(10) 0.3907(11) 0.061(4) Uiso 1.000000
H H16b_2 0.2055(19) 0.6939(11) 0.2826(11) 0.063(4) Uiso 1.000000
H H16c_2 0.187(2) 0.5814(12) 0.3640(11) 0.075(5) Uiso 1.000000
C C17_2 0.5973(2) 0.61725(10) 0.52889(10) 0.0379(3) Uani 1.000000
H H17a_2 0.513(2) 0.6183(12) 0.5923(13) 0.078(5) Uiso 1.000000
H H17b_2 0.6689(18) 0.5546(10) 0.5403(10) 0.053(4) Uiso 1.000000
H H17c_2 0.691(2) 0.6769(12) 0.5007(11) 0.063(4) Uiso 1.000000
N N1_2 0.54919(11) 0.65749(6) 0.05356(6) 0.01600(18) Uani 1.000000
N N2_2 0.97000(11) 0.68391(6) -0.23867(6) 0.01570(18) Uani 1.000000
H H2a_2 0.9130(17) 0.6344(9) -0.1783(10) 0.034(3) Uiso 1.000000
N N3_2 0.73649(10) 0.62313(5) -0.06356(6) 0.01434(17) Uani 1.000000
N N4_2 0.71695(11) 0.61835(6) 0.20201(6) 0.0216(2) Uani 1.000000
N N5_2 0.73631(12) 0.60823(6) 0.35843(6) 0.0252(2) Uani 1.000000
O O1_2 0.96957(9) 0.83717(5) -0.32943(5) 0.01908(16) Uani 1.000000
O O2_2 0.48417(11) 0.62231(5) 0.46393(5) 0.02792(19) Uani 1.000000
F F1_2 0.85963(9) 0.55284(5) -0.31786(5) 0.03320(17) Uani 1.000000
loop_
_atom_type_symbol
_atom_type_scat_dispersion_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
F 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.01794 0.01033 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
H 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
N 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.00653 0.00323 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
O 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -1.00 0.0070
0.00 1.00 1.00 0.0070
1.00 1.00 -1.00 0.0480
-1.00 -1.00 1.00 0.0210
0.00 -1.00 1.00 0.0260
-1.00 0.00 0.00 0.0270
-1.00 0.00 -1.00 0.0230
0.00 1.00 -1.00 0.0390
-1.00 1.00 -1.00 0.0210
1.00 -1.00 1.00 0.0220
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1_1 C2_1 H2_1 . . 121.8(6) ?
N3_1 C2_1 H2_1 . . 124.5(6) ?
N3_1 C2_1 N1_1 . . 113.70(9) ?
C7A_1 C3A_1 C4_1 . . 119.54(8) ?
N3_1 C3A_1 C4_1 . . 130.61(9) ?
N3_1 C3A_1 C7A_1 . . 109.75(8) ?
C5_1 C4_1 C3A_1 . . 117.17(9) ?
C8_1 C4_1 C3A_1 . . 124.80(9) ?
C8_1 C4_1 C5_1 . . 117.82(9) ?
H5_1 C5_1 C4_1 . . 118.1(6) ?
C6_1 C5_1 C4_1 . . 122.32(10) ?
C6_1 C5_1 H5_1 . . 119.6(6) ?
H6_1 C6_1 C5_1 . . 118.4(7) ?
C7_1 C6_1 C5_1 . . 121.32(10) ?
C7_1 C6_1 H6_1 . . 120.3(7) ?
H7_1 C7_1 C6_1 . . 120.2(7) ?
C7A_1 C7_1 C6_1 . . 116.21(10) ?
C7A_1 C7_1 H7_1 . . 123.5(7) ?
C7_1 C7A_1 C3A_1 . . 123.43(9) ?
N1_1 C7A_1 C3A_1 . . 105.24(8) ?
N1_1 C7A_1 C7_1 . . 131.26(9) ?
N2_1 C8_1 C4_1 . . 116.58(9) ?
O1_1 C8_1 C4_1 . . 121.17(9) ?
O1_1 C8_1 N2_1 . . 122.15(10) ?
H9b_1 C9_1 H9a_1 . . 114.0(11) ?
C10_1 C9_1 H9a_1 . . 105.0(8) ?
C10_1 C9_1 H9b_1 . . 106.5(7) ?
N2_1 C9_1 H9a_1 . . 108.6(7) ?
N2_1 C9_1 H9b_1 . . 109.1(7) ?
N2_1 C9_1 C10_1 . . 113.74(10) ?
H10a_1 C10_1 C9_1 . . 109.9(7) ?
H10b_1 C10_1 C9_1 . . 111.7(7) ?
H10b_1 C10_1 H10a_1 . . 114.6(10) ?
F1_1 C10_1 C9_1 . . 109.35(10) ?
F1_1 C10_1 H10a_1 . . 106.5(7) ?
F1_1 C10_1 H10b_1 . . 104.4(7) ?
H11b_1 C11_1 H11a_1 . . 109.0(10) ?
C12_1 C11_1 H11a_1 . . 108.2(7) ?
C12_1 C11_1 H11b_1 . . 108.6(7) ?
N1_1 C11_1 H11a_1 . . 107.6(7) ?
N1_1 C11_1 H11b_1 . . 109.8(7) ?
N1_1 C11_1 C12_1 . . 113.63(8) ?
C13_1 C12_1 C11_1 . . 120.19(8) ?
N4_1 C12_1 C11_1 . . 116.34(8) ?
N4_1 C12_1 C13_1 . . 123.40(8) ?
C14_1 C13_1 C12_1 . . 114.47(8) ?
C16_1 C13_1 C12_1 . . 124.13(9) ?
C16_1 C13_1 C14_1 . . 121.40(9) ?
N5_1 C14_1 C13_1 . . 123.18(9) ?
O2_1 C14_1 C13_1 . . 117.08(8) ?
O2_1 C14_1 N5_1 . . 119.74(8) ?
N4_1 C15_1 H15_1 . . 117.2(6) ?
N5_1 C15_1 H15_1 . . 116.0(6) ?
N5_1 C15_1 N4_1 . . 126.82(9) ?
H16a_1 C16_1 C13_1 . . 111.8(7) ?
H16b_1 C16_1 C13_1 . . 113.0(7) ?
H16b_1 C16_1 H16a_1 . . 102.7(10) ?
H16c_1 C16_1 C13_1 . . 111.6(8) ?
H16c_1 C16_1 H16a_1 . . 108.3(11) ?
H16c_1 C16_1 H16b_1 . . 109.1(11) ?
H17b_1 C17_1 H17a_1 . . 110.8(9) ?
H17c_1 C17_1 H17a_1 . . 108.6(9) ?
H17c_1 C17_1 H17b_1 . . 109.7(9) ?
O2_1 C17_1 H17a_1 . . 105.9(6) ?
O2_1 C17_1 H17b_1 . . 110.8(6) ?
O2_1 C17_1 H17c_1 . . 111.0(6) ?
C7A_1 N1_1 C2_1 . . 106.63(8) ?
C11_1 N1_1 C2_1 . . 126.92(9) ?
C11_1 N1_1 C7A_1 . . 126.35(8) ?
C9_1 N2_1 C8_1 . . 119.57(10) ?
H2a_1 N2_1 C8_1 . . 118.7(8) ?
H2a_1 N2_1 C9_1 . . 120.7(8) ?
C3A_1 N3_1 C2_1 . . 104.67(8) ?
C15_1 N4_1 C12_1 . . 115.96(8) ?
C15_1 N5_1 C14_1 . . 116.15(8) ?
C17_1 O2_1 C14_1 . . 117.07(8) ?
N1_2 C2_2 H2_2 . . 121.1(7) ?
N3_2 C2_2 H2_2 . . 125.3(7) ?
N3_2 C2_2 N1_2 . . 113.60(9) ?
C7A_2 C3A_2 C4_2 . . 120.12(8) ?
N3_2 C3A_2 C4_2 . . 130.02(9) ?
N3_2 C3A_2 C7A_2 . . 109.86(8) ?
C5_2 C4_2 C3A_2 . . 117.23(9) ?
C8_2 C4_2 C3A_2 . . 123.55(8) ?
C8_2 C4_2 C5_2 . . 119.22(9) ?
H5_2 C5_2 C4_2 . . 117.9(6) ?
C6_2 C5_2 C4_2 . . 121.84(9) ?
C6_2 C5_2 H5_2 . . 120.2(6) ?
H6_2 C6_2 C5_2 . . 120.5(6) ?
C7_2 C6_2 C5_2 . . 121.47(9) ?
C7_2 C6_2 H6_2 . . 118.0(6) ?
H7_2 C7_2 C6_2 . . 120.4(6) ?
C7A_2 C7_2 C6_2 . . 116.54(9) ?
C7A_2 C7_2 H7_2 . . 123.1(6) ?
C7_2 C7A_2 C3A_2 . . 122.79(9) ?
N1_2 C7A_2 C3A_2 . . 105.16(8) ?
N1_2 C7A_2 C7_2 . . 132.05(9) ?
N2_2 C8_2 C4_2 . . 115.46(8) ?
O1_2 C8_2 C4_2 . . 121.45(8) ?
O1_2 C8_2 N2_2 . . 123.08(9) ?
H9b_2 C9_2 H9a_2 . . 110.2(9) ?
C10_2 C9_2 H9a_2 . . 107.5(7) ?
C10_2 C9_2 H9b_2 . . 107.5(6) ?
N2_2 C9_2 H9a_2 . . 109.5(7) ?
N2_2 C9_2 H9b_2 . . 109.8(6) ?
N2_2 C9_2 C10_2 . . 112.27(9) ?
H10a_2 C10_2 C9_2 . . 110.4(7) ?
H10b_2 C10_2 C9_2 . . 111.2(7) ?
H10b_2 C10_2 H10a_2 . . 113.6(10) ?
F1_2 C10_2 C9_2 . . 108.97(9) ?
F1_2 C10_2 H10a_2 . . 106.7(7) ?
F1_2 C10_2 H10b_2 . . 105.6(7) ?
H11b_2 C11_2 H11a_2 . . 108.4(9) ?
C12_2 C11_2 H11a_2 . . 109.4(6) ?
C12_2 C11_2 H11b_2 . . 109.5(7) ?
N1_2 C11_2 H11a_2 . . 108.5(6) ?
N1_2 C11_2 H11b_2 . . 106.9(6) ?
N1_2 C11_2 C12_2 . . 113.96(8) ?
C13_2 C12_2 C11_2 . . 119.79(9) ?
N4_2 C12_2 C11_2 . . 117.08(9) ?
N4_2 C12_2 C13_2 . . 123.11(9) ?
C14_2 C13_2 C12_2 . . 114.56(9) ?
C16_2 C13_2 C12_2 . . 124.46(9) ?
C16_2 C13_2 C14_2 . . 120.97(9) ?
N5_2 C14_2 C13_2 . . 123.50(10) ?
O2_2 C14_2 C13_2 . . 116.73(10) ?
O2_2 C14_2 N5_2 . . 119.77(9) ?
N4_2 C15_2 H15_2 . . 117.0(7) ?
N5_2 C15_2 H15_2 . . 115.9(7) ?
N5_2 C15_2 N4_2 . . 127.12(10) ?
H16a_2 C16_2 C13_2 . . 111.5(8) ?
H16b_2 C16_2 C13_2 . . 113.1(8) ?
H16b_2 C16_2 H16a_2 . . 101.5(11) ?
H16c_2 C16_2 C13_2 . . 111.4(9) ?
H16c_2 C16_2 H16a_2 . . 108.5(12) ?
H16c_2 C16_2 H16b_2 . . 110.3(12) ?
H17b_2 C17_2 H17a_2 . . 110.4(12) ?
H17c_2 C17_2 H17a_2 . . 111.0(12) ?
H17c_2 C17_2 H17b_2 . . 108.9(11) ?
O2_2 C17_2 H17a_2 . . 106.2(9) ?
O2_2 C17_2 H17b_2 . . 110.5(7) ?
O2_2 C17_2 H17c_2 . . 109.9(8) ?
C7A_2 N1_2 C2_2 . . 106.66(8) ?
C11_2 N1_2 C2_2 . . 126.10(9) ?
C11_2 N1_2 C7A_2 . . 126.98(9) ?
C9_2 N2_2 C8_2 . . 122.13(9) ?
H2a_2 N2_2 C8_2 . . 118.6(7) ?
H2a_2 N2_2 C9_2 . . 118.4(7) ?
C3A_2 N3_2 C2_2 . . 104.70(8) ?
C15_2 N4_2 C12_2 . . 115.91(9) ?
C15_2 N5_2 C14_2 . . 115.79(9) ?
C17_2 O2_2 C14_2 . . 116.88(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2_1 H2_1 . 1.054(12) ?
C2_1 N1_1 . 1.3551(13) ?
C2_1 N3_1 . 1.3175(13) ?
C3A_1 C4_1 . 1.4063(14) ?
C3A_1 C7A_1 . 1.4051(13) ?
C3A_1 N3_1 . 1.3871(13) ?
C4_1 C5_1 . 1.3892(14) ?
C4_1 C8_1 . 1.4922(14) ?
C5_1 H5_1 . 1.082(13) ?
C5_1 C6_1 . 1.3982(15) ?
C6_1 H6_1 . 1.064(13) ?
C6_1 C7_1 . 1.3923(16) ?
C7_1 H7_1 . 1.031(12) ?
C7_1 C7A_1 . 1.3898(14) ?
C7A_1 N1_1 . 1.3834(13) ?
C8_1 N2_1 . 1.3479(14) ?
C8_1 O1_1 . 1.2289(12) ?
C9_1 H9a_1 . 1.092(15) ?
C9_1 H9b_1 . 1.096(14) ?
C9_1 C10_1 . 1.5021(16) ?
C9_1 N2_1 . 1.4475(14) ?
C10_1 H10a_1 . 1.091(15) ?
C10_1 H10b_1 . 1.094(14) ?
C10_1 F1_1 . 1.3871(13) ?
C11_1 H11a_1 . 1.076(14) ?
C11_1 H11b_1 . 1.073(13) ?
C11_1 C12_1 . 1.5107(14) ?
C11_1 N1_1 . 1.4481(13) ?
C12_1 C13_1 . 1.3849(13) ?
C12_1 N4_1 . 1.3447(12) ?
C13_1 C14_1 . 1.4129(13) ?
C13_1 C16_1 . 1.4938(14) ?
C14_1 N5_1 . 1.3244(12) ?
C14_1 O2_1 . 1.3349(11) ?
C15_1 H15_1 . 1.100(11) ?
C15_1 N4_1 . 1.3227(13) ?
C15_1 N5_1 . 1.3358(13) ?
C16_1 H16a_1 . 1.076(14) ?
C16_1 H16b_1 . 1.055(14) ?
C16_1 H16c_1 . 1.032(16) ?
C17_1 H17a_1 . 1.065(13) ?
C17_1 H17b_1 . 1.092(12) ?
C17_1 H17c_1 . 1.096(13) ?
C17_1 O2_1 . 1.4378(12) ?
N2_1 H2a_1 . 1.002(14) ?
C2_2 H2_2 . 1.060(13) ?
C2_2 N1_2 . 1.3599(13) ?
C2_2 N3_2 . 1.3133(13) ?
C3A_2 C4_2 . 1.4043(13) ?
C3A_2 C7A_2 . 1.4042(13) ?
C3A_2 N3_2 . 1.3877(12) ?
C4_2 C5_2 . 1.3926(14) ?
C4_2 C8_2 . 1.4929(14) ?
C5_2 H5_2 . 1.101(12) ?
C5_2 C6_2 . 1.4029(14) ?
C6_2 H6_2 . 1.070(12) ?
C6_2 C7_2 . 1.3910(15) ?
C7_2 H7_2 . 1.059(12) ?
C7_2 C7A_2 . 1.3932(14) ?
C7A_2 N1_2 . 1.3812(13) ?
C8_2 N2_2 . 1.3448(13) ?
C8_2 O1_2 . 1.2346(11) ?
C9_2 H9a_2 . 1.064(12) ?
C9_2 H9b_2 . 1.090(13) ?
C9_2 C10_2 . 1.5073(16) ?
C9_2 N2_2 . 1.4450(13) ?
C10_2 H10a_2 . 1.078(13) ?
C10_2 H10b_2 . 1.066(14) ?
C10_2 F1_2 . 1.3989(14) ?
C11_2 H11a_2 . 1.102(13) ?
C11_2 H11b_2 . 1.092(12) ?
C11_2 C12_2 . 1.5169(14) ?
C11_2 N1_2 . 1.4456(13) ?
C12_2 C13_2 . 1.3869(14) ?
C12_2 N4_2 . 1.3422(13) ?
C13_2 C14_2 . 1.4111(14) ?
C13_2 C16_2 . 1.4974(15) ?
C14_2 N5_2 . 1.3228(14) ?
C14_2 O2_2 . 1.3344(13) ?
C15_2 H15_2 . 1.066(13) ?
C15_2 N4_2 . 1.3289(14) ?
C15_2 N5_2 . 1.3305(15) ?
C16_2 H16a_2 . 1.055(16) ?
C16_2 H16b_2 . 1.063(16) ?
C16_2 H16c_2 . 1.047(17) ?
C17_2 H17a_2 . 1.051(17) ?
C17_2 H17b_2 . 1.055(14) ?
C17_2 H17c_2 . 1.083(16) ?
C17_2 O2_2 . 1.4341(15) ?
N2_2 H2a_2 . 1.002(14) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2_1 H2_1 O1_2 2_665 1.054(12) 2.353(12) 3.2907(14) 147.5(9)
C7_1 H7_1 O1_2 2_765 1.031(12) 2.245(13) 3.2211(14) 157.4(10)
N2_1 H2a_1 N3_1 . 1.002(14) 2.035(14) 2.8581(14) 137.9(10)
C2_2 H2_2 N5_1 . 1.060(13) 2.240(13) 3.2922(15) 171.4(9)
C7_2 H7_2 O1_1 2_666 1.059(12) 2.394(12) 3.0915(14) 122.3(8)
C11_2 H11b_2 F1_1 2_566 1.092(12) 2.186(12) 3.1839(13) 150.7(10)
C16_2 H16c_2 F1_2 2_665 1.047(17) 2.403(17) 3.2827(15) 140.9(12)
N2_2 H2a_2 N3_2 . 1.002(14) 1.942(14) 2.7823(13) 139.6(10)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2_1 N1_1 C7A_1 C3A_1 . . . . 0.69(8) ?
C2_1 N1_1 C7A_1 C7_1 . . . . 177.71(8) ?
C2_1 N1_1 C11_1 C12_1 . . . . 101.85(10) ?
C2_1 N3_1 C3A_1 C4_1 . . . . -175.83(7) ?
C2_1 N3_1 C3A_1 C7A_1 . . . . 0.29(8) ?
C3A_1 C4_1 C5_1 C6_1 . . . . -0.47(11) ?
C3A_1 C4_1 C8_1 N2_1 . . . . -2.07(10) ?
C3A_1 C4_1 C8_1 O1_1 . . . . 174.32(10) ?
C3A_1 C7A_1 C7_1 C6_1 . . . . 0.27(11) ?
C3A_1 C7A_1 N1_1 C11_1 . . . . -175.96(7) ?
C4_1 C5_1 C6_1 C7_1 . . . . -0.58(12) ?
C4_1 C8_1 N2_1 C9_1 . . . . 166.74(9) ?
C5_1 C6_1 C7_1 C7A_1 . . . . 0.67(12) ?
C6_1 C7_1 C7A_1 N1_1 . . . . -176.29(8) ?
C7_1 C7A_1 N1_1 C11_1 . . . . 1.06(13) ?
C7A_1 N1_1 C11_1 C12_1 . . . . -82.17(10) ?
C8_1 N2_1 C9_1 C10_1 . . . . 84.98(10) ?
C11_1 C12_1 C13_1 C14_1 . . . . 177.37(9) ?
C11_1 C12_1 C13_1 C16_1 . . . . -2.24(12) ?
C11_1 C12_1 N4_1 C15_1 . . . . -177.50(9) ?
C12_1 C13_1 C14_1 N5_1 . . . . 0.49(10) ?
C12_1 C13_1 C14_1 O2_1 . . . . -179.87(8) ?
C12_1 N4_1 C15_1 N5_1 . . . . -0.46(10) ?
C13_1 C14_1 N5_1 C15_1 . . . . -1.16(11) ?
C13_1 C14_1 O2_1 C17_1 . . . . -175.94(9) ?
C14_1 N5_1 C15_1 N4_1 . . . . 1.18(10) ?
C2_2 N1_2 C7A_2 C3A_2 . . . . 1.07(8) ?
C2_2 N1_2 C7A_2 C7_2 . . . . -179.36(8) ?
C2_2 N1_2 C11_2 C12_2 . . . . 78.97(10) ?
C2_2 N3_2 C3A_2 C4_2 . . . . -179.62(7) ?
C2_2 N3_2 C3A_2 C7A_2 . . . . -0.08(8) ?
C3A_2 C4_2 C5_2 C6_2 . . . . -0.20(11) ?
C3A_2 C4_2 C8_2 N2_2 . . . . -8.31(10) ?
C3A_2 C4_2 C8_2 O1_2 . . . . 172.85(9) ?
C3A_2 C7A_2 C7_2 C6_2 . . . . 0.26(11) ?
C3A_2 C7A_2 N1_2 C11_2 . . . . 175.46(7) ?
C4_2 C5_2 C6_2 C7_2 . . . . -0.19(12) ?
C4_2 C8_2 N2_2 C9_2 . . . . 177.21(8) ?
C5_2 C6_2 C7_2 C7A_2 . . . . 0.16(11) ?
C6_2 C7_2 C7A_2 N1_2 . . . . -179.25(8) ?
C7_2 C7A_2 N1_2 C11_2 . . . . -4.97(14) ?
C7A_2 N1_2 C11_2 C12_2 . . . . -94.36(10) ?
C8_2 N2_2 C9_2 C10_2 . . . . -84.96(10) ?
C11_2 C12_2 C13_2 C14_2 . . . . 178.99(10) ?
C11_2 C12_2 C13_2 C16_2 . . . . -0.06(12) ?
C11_2 C12_2 N4_2 C15_2 . . . . -179.04(10) ?
C12_2 C13_2 C14_2 N5_2 . . . . -0.01(11) ?
C12_2 C13_2 C14_2 O2_2 . . . . 179.87(9) ?
C12_2 N4_2 C15_2 N5_2 . . . . 0.03(11) ?
C13_2 C14_2 N5_2 C15_2 . . . . -0.37(12) ?
C13_2 C14_2 O2_2 C17_2 . . . . -175.04(10) ?
C14_2 N5_2 C15_2 N4_2 . . . . 0.38(11) ?

_cod_database_fobs_code 2244212
