#------------------------------------------------------------------------------
#$Date: 2024-11-20 04:01:22 +0200 (Wed, 20 Nov 2024) $
#$Revision: 296002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249600.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_7249600
loop_
_publ_author_name
'Azzouzi, Mohamed'
'Ouchaoui, Abderrahim Ait'
'Azougagh, Omar'
'El Hadad, Salah Eddine'
'Abou-salama, Mohamed'
'Oussaid, Adyl'
'Pannecouque, Christophe'
'Rohand, Taoufik'
_publ_section_title
;
 Synthesis, crystal structure, and antiviral evaluation of new
 imidazopyridine-schiff base derivatives: in vitro and in silico anti-HIV
 studies
;
_journal_issue                   50
_journal_name_full               'RSC Advances'
_journal_page_first              36902
_journal_page_last               36918
_journal_paper_doi               10.1039/D4RA07561G
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C20 H13 Cl N4 O2'
_chemical_formula_sum            'C20 H13 Cl N4 O2'
_chemical_formula_weight         376.79
_chemical_name_systematic
(E)-N-(6-chloro-2-phenylimidazo[1,2-a]pyridin-3-yl)-1-(4-nitrophenyl)methanimine
_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   difmap
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2l8kt8
_audit_creation_date             2023-11-14
_audit_creation_method
;FinalCif V130 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-10-16 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.178(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7755(6)
_cell_length_b                   26.7963(15)
_cell_length_c                   12.0718(6)
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    150
_cell_measurement_theta_max      78.275
_cell_measurement_theta_min      3.562
_cell_volume                     3407.2(3)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 4 (2022) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            114388
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         79.153
_diffrn_reflns_theta_min         3.561
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_T_max  0.3293
_exptl_absorpt_correction_T_min  0.2094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1349 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.6359.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_recrystallization_method 'crystallized from CHCl3'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         11104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0478P)²+0.9569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9165
_reflns_number_total             11104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra07561g2.cif
_cod_data_source_block           azzo051
_cod_database_code               7249600
_olex2_date_sample_data_collection 2023-11-13
_olex2_date_sample_submission    2023-11-10
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_refinement_description
;
;
_olex2_submission_original_sample_id MFU-MA-05
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2019/3
_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_min   0.835
_shelx_estimated_absorpt_t_max   0.945
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
Cl1A Cl 1.08146(3) 0.47391(2) 0.39378(3) 0.04834(9) Uani 1 1 d . . . . .
O1A O 1.11878(12) 0.16977(5) 0.92667(10) 0.0608(3) Uani 1 1 d . . . . .
N1A N 0.78480(9) 0.38462(3) 0.33844(7) 0.02696(17) Uani 1 1 d . . . . .
C1A C 0.72475(10) 0.34341(4) 0.37370(8) 0.02681(19) Uani 1 1 d . . . . .
H13A H 0.5006(16) 0.2963(6) 0.4368(14) 0.039(4) Uiso 1 1 d . . . . .
O2A O 1.09415(11) 0.24129(6) 1.00249(8) 0.0589(3) Uani 1 1 d . . . . .
N2A N 0.62338(9) 0.36510(4) 0.19466(7) 0.02913(18) Uani 1 1 d . . . . .
C2A C 0.62428(10) 0.33268(4) 0.28272(8) 0.02726(19) Uani 1 1 d . . . . .
N3A N 0.77985(9) 0.32453(4) 0.47890(7) 0.02831(18) Uani 1 1 d . . . . .
C3A C 0.72154(11) 0.39570(4) 0.22861(9) 0.0280(2) Uani 1 1 d . . . . .
N4A N 1.07368(11) 0.21181(5) 0.92265(9) 0.0425(3) Uani 1 1 d . . . . .
C4A C 0.76882(12) 0.43447(5) 0.16968(9) 0.0320(2) Uani 1 1 d . . . . .
H4A H 0.7205(15) 0.4429(6) 0.0948(13) 0.039(4) Uiso 1 1 d . . . . .
C5A C 0.87767(12) 0.45857(5) 0.22112(10) 0.0337(2) Uani 1 1 d . . . . .
H5A H 0.9112(16) 0.4847(6) 0.1828(13) 0.038(4) Uiso 1 1 d . . . . .
C6A C 0.93970(12) 0.44481(5) 0.33271(10) 0.0329(2) Uani 1 1 d . . . . .
C7A C 0.89395(11) 0.40866(4) 0.39177(9) 0.0303(2) Uani 1 1 d . . . . .
H7A H 0.9326(15) 0.3976(6) 0.4703(13) 0.034(4) Uiso 1 1 d . . . . .
C8A C 0.52375(10) 0.29481(4) 0.27168(9) 0.02760(19) Uani 1 1 d . . . . .
C9A C 0.47550(12) 0.27393(5) 0.16477(9) 0.0317(2) Uani 1 1 d . . . . .
H9A H 0.5133(15) 0.2836(6) 0.1039(13) 0.033(4) Uiso 1 1 d . . . . .
C10A C 0.37479(12) 0.24068(5) 0.14952(9) 0.0334(2) Uani 1 1 d . . . . .
H10A H 0.3419(16) 0.2260(6) 0.0739(14) 0.041(4) Uiso 1 1 d . . . . .
C11A C 0.31964(12) 0.22773(5) 0.23942(10) 0.0333(2) Uani 1 1 d . . . . .
H11A H 0.2490(16) 0.2057(6) 0.2275(13) 0.038(4) Uiso 1 1 d . . . . .
C12A C 0.36795(12) 0.24763(5) 0.34601(10) 0.0353(2) Uani 1 1 d . . . . .
H12A H 0.3312(16) 0.2373(7) 0.4097(14) 0.043(4) Uiso 1 1 d . . . . .
C13A C 0.46926(12) 0.28096(5) 0.36233(9) 0.0321(2) Uani 1 1 d . . . . .
C14A C 0.77204(11) 0.27838(4) 0.50462(9) 0.0284(2) Uani 1 1 d . . . . .
H14A H 0.7255(15) 0.2531(6) 0.4532(13) 0.036(4) Uiso 1 1 d . . . . .
C15A C 0.84085(10) 0.26058(4) 0.61570(8) 0.02728(19) Uani 1 1 d . . . . .
C16A C 0.86885(12) 0.20994(4) 0.63216(9) 0.0307(2) Uani 1 1 d . . . . .
H16A H 0.8360(15) 0.1863(6) 0.5719(14) 0.039(4) Uiso 1 1 d . . . . .
C17A C 0.94764(12) 0.19370(5) 0.73237(10) 0.0326(2) Uani 1 1 d . . . . .
H17A H 0.9713(16) 0.1591(7) 0.7422(14) 0.042(4) Uiso 1 1 d . . . . .
C18A C 0.99091(11) 0.22859(5) 0.81649(9) 0.0329(2) Uani 1 1 d . . . . .
C19A C 0.96028(12) 0.27872(5) 0.80441(9) 0.0353(2) Uani 1 1 d . . . . .
H19A H 0.9902(17) 0.3020(6) 0.8628(15) 0.044(4) Uiso 1 1 d . . . . .
C20A C 0.88606(12) 0.29476(5) 0.70272(9) 0.0319(2) Uani 1 1 d . . . . .
H20A H 0.8657(15) 0.3296(6) 0.6905(13) 0.034(4) Uiso 1 1 d . . . . .
Cl1B Cl 0.90163(3) 0.60848(2) 0.29154(3) 0.04510(8) Uani 1 1 d . . . . .
O1B O 0.65822(10) 0.33742(4) 0.88807(8) 0.0469(2) Uani 1 1 d . . . . .
N1B N 0.58525(9) 0.53087(3) 0.22032(7) 0.02735(17) Uani 1 1 d . . . . .
C1B C 0.51166(11) 0.49246(4) 0.25075(8) 0.02729(19) Uani 1 1 d . . . . .
O2B O 0.82186(10) 0.38472(4) 0.89311(8) 0.0449(2) Uani 1 1 d . . . . .
N2B N 0.40978(9) 0.52631(4) 0.08275(7) 0.02855(18) Uani 1 1 d . . . . .
C2B C 0.40440(11) 0.49003(4) 0.16133(8) 0.02726(19) Uani 1 1 d . . . . .
H16B H 0.3982(16) 0.3780(6) 0.5358(14) 0.040(4) Uiso 1 1 d . . . . .
N3B N 0.55856(9) 0.47105(3) 0.35455(7) 0.02818(18) Uani 1 1 d . . . . .
C3B C 0.51891(11) 0.55058(4) 0.11883(8) 0.0280(2) Uani 1 1 d . . . . .
N4B N 0.71697(10) 0.36890(4) 0.84629(8) 0.0340(2) Uani 1 1 d . . . . .
C4B C 0.57216(12) 0.59100(4) 0.07005(9) 0.0308(2) Uani 1 1 d . . . . .
H4B H 0.5253(16) 0.6060(6) 0.0005(14) 0.040(4) Uiso 1 1 d . . . . .
C5B C 0.68866(12) 0.60877(5) 0.12315(10) 0.0328(2) Uani 1 1 d . . . . .
H5B H 0.7281(16) 0.6346(7) 0.0905(14) 0.043(4) Uiso 1 1 d . . . . .
C6B C 0.75243(12) 0.58663(5) 0.22649(10) 0.0323(2) Uani 1 1 d . . . . .
C7B C 0.70108(11) 0.54853(4) 0.27575(9) 0.0303(2) Uani 1 1 d . . . . .
H7B H 0.7395(15) 0.5318(6) 0.3479(13) 0.034(4) Uiso 1 1 d . . . . .
C8B C 0.29857(11) 0.45427(4) 0.13836(8) 0.0279(2) Uani 1 1 d . . . . .
C9B C 0.18347(11) 0.46965(5) 0.06976(10) 0.0331(2) Uani 1 1 d . . . . .
H9B H 0.1734(16) 0.5044(7) 0.0417(14) 0.044(4) Uiso 1 1 d . . . . .
C10B C 0.08547(12) 0.43586(5) 0.03587(11) 0.0375(3) Uani 1 1 d . . . . .
H10B H 0.0042(17) 0.4468(7) -0.0109(15) 0.048(5) Uiso 1 1 d . . . . .
C11B C 0.09940(12) 0.38633(5) 0.07132(11) 0.0366(2) Uani 1 1 d . . . . .
H11B H 0.0336(17) 0.3639(7) 0.0480(14) 0.044(4) Uiso 1 1 d . . . . .
C12B C 0.21337(12) 0.37072(5) 0.14002(10) 0.0346(2) Uani 1 1 d . . . . .
H12B H 0.2228(16) 0.3359(6) 0.1640(13) 0.039(4) Uiso 1 1 d . . . . .
C13B C 0.31247(11) 0.40440(4) 0.17231(9) 0.0304(2) Uani 1 1 d . . . . .
H13B H 0.3926(15) 0.3920(6) 0.2154(13) 0.035(4) Uiso 1 1 d . . . . .
C14B C 0.49377(11) 0.44323(4) 0.40758(9) 0.0299(2) Uani 1 1 d . . . . .
H14B H 0.4057(15) 0.4345(6) 0.3787(13) 0.035(4) Uiso 1 1 d . . . . .
C15B C 0.55226(11) 0.42373(4) 0.52008(8) 0.02723(19) Uani 1 1 d . . . . .
C16B C 0.48594(11) 0.38976(4) 0.57369(9) 0.0303(2) Uani 1 1 d . . . . .
C17B C 0.54026(12) 0.37133(4) 0.68085(9) 0.0308(2) Uani 1 1 d . . . . .
H17B H 0.4943(15) 0.3486(6) 0.7196(13) 0.037(4) Uiso 1 1 d . . . . .
C18B C 0.65933(11) 0.38835(4) 0.73321(8) 0.0286(2) Uani 1 1 d . . . . .
C19B C 0.72756(11) 0.42236(5) 0.68296(9) 0.0313(2) Uani 1 1 d . . . . .
H19B H 0.8110(16) 0.4343(7) 0.7222(14) 0.044(4) Uiso 1 1 d . . . . .
C20B C 0.67350(11) 0.43955(4) 0.57557(9) 0.0304(2) Uani 1 1 d . . . . .
H20B H 0.7205(16) 0.4629(6) 0.5372(14) 0.039(4) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
C3A N1A C1A 107.18(9) . . ?
C7A N1A C1A 129.44(9) . . ?
C7A N1A C3A 123.06(10) . . ?
N1A C1A C2A 104.81(9) . . ?
N3A C1A N1A 115.79(9) . . ?
N3A C1A C2A 139.33(11) . . ?
C3A N2A C2A 106.02(9) . . ?
C1A C2A C8A 130.26(10) . . ?
N2A C2A C1A 110.86(10) . . ?
N2A C2A C8A 118.85(9) . . ?
C14A N3A C1A 122.62(10) . . ?
N1A C3A C4A 118.76(10) . . ?
N2A C3A N1A 111.09(9) . . ?
N2A C3A C4A 130.12(10) . . ?
O1A N4A O2A 123.80(12) . . ?
O1A N4A C18A 118.63(12) . . ?
O2A N4A C18A 117.56(13) . . ?
C3A C4A H4A 117.4(10) . . ?
C5A C4A C3A 118.95(10) . . ?
C5A C4A H4A 123.6(10) . . ?
C4A C5A H5A 120.3(10) . . ?
C4A C5A C6A 119.67(11) . . ?
C6A C5A H5A 120.1(10) . . ?
C5A C6A Cl1A 118.84(9) . . ?
C7A C6A Cl1A 118.88(9) . . ?
C7A C6A C5A 122.25(11) . . ?
N1A C7A H7A 116.8(9) . . ?
C6A C7A N1A 117.27(10) . . ?
C6A C7A H7A 126.0(9) . . ?
C9A C8A C2A 118.83(10) . . ?
C13A C8A C2A 122.41(10) . . ?
C13A C8A C9A 118.65(11) . . ?
C8A C9A H9A 117.9(9) . . ?
C10A C9A C8A 120.45(11) . . ?
C10A C9A H9A 121.7(9) . . ?
C9A C10A H10A 119.7(10) . . ?
C9A C10A C11A 120.63(10) . . ?
C11A C10A H10A 119.7(10) . . ?
C10A C11A H11A 119.9(10) . . ?
C10A C11A C12A 119.37(11) . . ?
C12A C11A H11A 120.7(10) . . ?
C11A C12A H12A 119.1(10) . . ?
C11A C12A C13A 120.47(11) . . ?
C13A C12A H12A 120.4(10) . . ?
C8A C13A H13A 119.0(10) . . ?
C12A C13A H13A 120.5(10) . . ?
C12A C13A C8A 120.42(10) . . ?
N3A C14A H14A 124.3(9) . . ?
N3A C14A C15A 119.22(10) . . ?
C15A C14A H14A 116.4(9) . . ?
C16A C15A C14A 119.89(10) . . ?
C16A C15A C20A 119.90(10) . . ?
C20A C15A C14A 120.06(10) . . ?
C15A C16A H16A 119.5(10) . . ?
C17A C16A C15A 120.09(11) . . ?
C17A C16A H16A 120.3(10) . . ?
C16A C17A H17A 120.4(10) . . ?
C18A C17A C16A 118.33(11) . . ?
C18A C17A H17A 121.3(10) . . ?
C17A C18A N4A 118.75(12) . . ?
C19A C18A N4A 118.46(11) . . ?
C19A C18A C17A 122.79(10) . . ?
C18A C19A H19A 121.7(10) . . ?
C18A C19A C20A 118.37(11) . . ?
C20A C19A H19A 119.9(11) . . ?
C15A C20A H20A 119.2(9) . . ?
C19A C20A C15A 120.40(11) . . ?
C19A C20A H20A 120.4(9) . . ?
C3B N1B C1B 107.34(9) . . ?
C7B N1B C1B 129.51(9) . . ?
C7B N1B C3B 123.14(10) . . ?
N1B C1B C2B 104.64(9) . . ?
N3B C1B N1B 115.35(9) . . ?
N3B C1B C2B 139.92(11) . . ?
C3B N2B C2B 106.46(9) . . ?
C1B C2B C8B 130.84(10) . . ?
N2B C2B C1B 110.55(10) . . ?
N2B C2B C8B 118.48(9) . . ?
C14B N3B C1B 124.36(10) . . ?
N1B C3B C4B 118.82(10) . . ?
N2B C3B N1B 110.95(9) . . ?
N2B C3B C4B 130.24(10) . . ?
O1B N4B O2B 123.62(10) . . ?
O1B N4B C18B 118.19(10) . . ?
O2B N4B C18B 118.19(10) . . ?
C3B C4B H4B 119.7(10) . . ?
C5B C4B C3B 119.01(10) . . ?
C5B C4B H4B 121.3(10) . . ?
C4B C5B H5B 120.7(10) . . ?
C4B C5B C6B 119.46(11) . . ?
C6B C5B H5B 119.8(10) . . ?
C5B C6B Cl1B 119.13(9) . . ?
C7B C6B Cl1B 118.69(9) . . ?
C7B C6B C5B 122.18(11) . . ?
N1B C7B H7B 116.2(9) . . ?
C6B C7B N1B 117.37(10) . . ?
C6B C7B H7B 126.4(9) . . ?
C9B C8B C2B 118.35(10) . . ?
C13B C8B C2B 122.50(10) . . ?
C13B C8B C9B 118.81(11) . . ?
C8B C9B H9B 119.9(10) . . ?
C10B C9B C8B 120.47(11) . . ?
C10B C9B H9B 119.5(10) . . ?
C9B C10B H10B 120.4(11) . . ?
C9B C10B C11B 120.39(11) . . ?
C11B C10B H10B 119.2(11) . . ?
C10B C11B H11B 119.9(11) . . ?
C10B C11B C12B 119.56(12) . . ?
C12B C11B H11B 120.5(11) . . ?
C11B C12B H12B 119.2(10) . . ?
C13B C12B C11B 120.04(12) . . ?
C13B C12B H12B 120.8(10) . . ?
C8B C13B H13B 121.0(10) . . ?
C12B C13B C8B 120.71(10) . . ?
C12B C13B H13B 118.2(10) . . ?
N3B C14B H14B 123.8(9) . . ?
N3B C14B C15B 119.78(10) . . ?
C15B C14B H14B 116.4(9) . . ?
C16B C15B C14B 119.92(10) . . ?
C16B C15B C20B 119.44(10) . . ?
C20B C15B C14B 120.63(10) . . ?
C15B C16B H16B 120.9(9) . . ?
C17B C16B H16B 118.7(10) . . ?
C17B C16B C15B 120.34(11) . . ?
C16B C17B H17B 121.0(9) . . ?
C18B C17B C16B 118.38(11) . . ?
C18B C17B H17B 120.5(9) . . ?
C17B C18B N4B 118.49(10) . . ?
C17B C18B C19B 122.86(10) . . ?
C19B C18B N4B 118.64(10) . . ?
C18B C19B H19B 121.4(10) . . ?
C20B C19B C18B 118.10(11) . . ?
C20B C19B H19B 120.5(10) . . ?
C15B C20B H20B 119.3(9) . . ?
C19B C20B C15B 120.86(11) . . ?
C19B C20B H20B 119.9(10) . . ?
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
Cl1A C6A 1.7349(12) . ?
O1A N4A 1.2238(18) . ?
N1A C1A 1.3912(14) . ?
N1A C3A 1.3890(13) . ?
N1A C7A 1.3760(14) . ?
C1A C2A 1.3997(14) . ?
C1A N3A 1.3796(13) . ?
O2A N4A 1.2295(17) . ?
N2A C2A 1.3712(14) . ?
N2A C3A 1.3328(15) . ?
C2A C8A 1.4698(16) . ?
N3A C14A 1.2821(15) . ?
C3A C4A 1.4134(16) . ?
N4A C18A 1.4690(14) . ?
C4A H4A 0.970(16) . ?
C4A C5A 1.3679(17) . ?
C5A H5A 0.952(17) . ?
C5A C6A 1.4203(16) . ?
C6A C7A 1.3558(17) . ?
C7A H7A 0.997(15) . ?
C8A C9A 1.4022(15) . ?
C8A C13A 1.3968(16) . ?
C9A H9A 0.948(16) . ?
C9A C10A 1.3861(17) . ?
C10A H10A 0.989(16) . ?
C10A C11A 1.3868(17) . ?
C11A H11A 0.951(17) . ?
C11A C12A 1.3885(16) . ?
C12A H12A 0.976(17) . ?
C12A C13A 1.3919(17) . ?
C13A H13A 0.981(16) . ?
C14A H14A 0.982(16) . ?
C14A C15A 1.4684(14) . ?
C15A C16A 1.3952(16) . ?
C15A C20A 1.4014(15) . ?
C16A H16A 0.972(16) . ?
C16A C17A 1.3930(15) . ?
C17A H17A 0.962(18) . ?
C17A C18A 1.3867(17) . ?
C18A C19A 1.3836(19) . ?
C19A H19A 0.946(17) . ?
C19A C20A 1.3846(16) . ?
C20A H20A 0.964(16) . ?
Cl1B C6B 1.7353(12) . ?
O1B N4B 1.2253(15) . ?
N1B C1B 1.3948(14) . ?
N1B C3B 1.3863(13) . ?
N1B C7B 1.3702(15) . ?
C1B C2B 1.4068(14) . ?
C1B N3B 1.3738(13) . ?
O2B N4B 1.2276(15) . ?
N2B C2B 1.3681(14) . ?
N2B C3B 1.3339(15) . ?
C2B C8B 1.4704(16) . ?
N3B C14B 1.2812(15) . ?
C3B C4B 1.4113(16) . ?
N4B C18B 1.4707(13) . ?
C4B H4B 0.971(16) . ?
C4B C5B 1.3690(17) . ?
C5B H5B 0.942(18) . ?
C5B C6B 1.4209(16) . ?
C6B C7B 1.3568(17) . ?
C7B H7B 0.989(15) . ?
C8B C9B 1.4001(15) . ?
C8B C13B 1.3966(16) . ?
C9B H9B 0.990(18) . ?
C9B C10B 1.3857(18) . ?
C10B H10B 0.982(18) . ?
C10B C11B 1.3927(19) . ?
C11B H11B 0.926(18) . ?
C11B C12B 1.3933(17) . ?
C12B H12B 0.976(17) . ?
C12B C13B 1.3897(17) . ?
C13B H13B 0.969(16) . ?
C14B H14B 0.968(16) . ?
C14B C15B 1.4674(14) . ?
C15B C16B 1.3977(16) . ?
C15B C20B 1.4021(15) . ?
C16B H16B 1.009(17) . ?
C16B C17B 1.3929(15) . ?
C17B H17B 0.965(16) . ?
C17B C18B 1.3826(16) . ?
C18B C19B 1.3883(17) . ?
C19B H19B 0.977(17) . ?
C19B C20B 1.3832(15) . ?
C20B H20B 0.981(17) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4A H4A N2B 0.970(16) 2.445(16) 3.4088(14) 172.7(14) 3_665 yes
C14A H14A O1B 0.982(16) 2.604(16) 3.5192(15) 155.0(12) 4_565 yes
C4B H4B N2A 0.971(16) 2.669(17) 3.6324(14) 171.6(14) 3_665 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1A C6A C7A N1A -176.73(9) . . . . ?
O1A N4A C18A C17A 11.95(18) . . . . ?
O1A N4A C18A C19A -167.54(13) . . . . ?
N1A C1A C2A N2A 0.99(12) . . . . ?
N1A C1A C2A C8A -176.74(11) . . . . ?
N1A C1A N3A C14A -151.06(11) . . . . ?
N1A C3A C4A C5A 2.31(17) . . . . ?
C1A N1A C3A N2A 2.10(13) . . . . ?
C1A N1A C3A C4A -176.06(10) . . . . ?
C1A N1A C7A C6A 172.89(11) . . . . ?
C1A C2A C8A C9A -148.14(12) . . . . ?
C1A C2A C8A C13A 35.70(18) . . . . ?
C1A N3A C14A C15A 175.74(10) . . . . ?
O2A N4A C18A C17A -168.49(12) . . . . ?
O2A N4A C18A C19A 12.02(18) . . . . ?
N2A C2A C8A C9A 34.29(15) . . . . ?
N2A C2A C8A C13A -141.87(11) . . . . ?
N2A C3A C4A C5A -175.45(12) . . . . ?
C2A C1A N3A C14A 25.3(2) . . . . ?
C2A N2A C3A N1A -1.46(13) . . . . ?
C2A N2A C3A C4A 176.44(12) . . . . ?
C2A C8A C9A C10A -175.56(11) . . . . ?
C2A C8A C13A C12A 175.26(11) . . . . ?
N3A C1A C2A N2A -175.58(13) . . . . ?
N3A C1A C2A C8A 6.7(2) . . . . ?
N3A C14A C15A C16A -158.92(11) . . . . ?
N3A C14A C15A C20A 16.65(17) . . . . ?
C3A N1A C1A C2A -1.80(12) . . . . ?
C3A N1A C1A N3A 175.71(9) . . . . ?
C3A N1A C7A C6A 0.25(17) . . . . ?
C3A N2A C2A C1A 0.26(13) . . . . ?
C3A N2A C2A C8A 178.28(10) . . . . ?
C3A C4A C5A C6A -0.96(18) . . . . ?
N4A C18A C19A C20A 177.68(11) . . . . ?
C4A C5A C6A Cl1A 177.09(10) . . . . ?
C4A C5A C6A C7A -0.8(2) . . . . ?
C5A C6A C7A N1A 1.20(18) . . . . ?
C7A N1A C1A C2A -175.35(11) . . . . ?
C7A N1A C1A N3A 2.17(17) . . . . ?
C7A N1A C3A N2A 176.16(10) . . . . ?
C7A N1A C3A C4A -2.00(16) . . . . ?
C8A C9A C10A C11A 0.37(19) . . . . ?
C9A C8A C13A C12A -0.91(18) . . . . ?
C9A C10A C11A C12A -1.33(19) . . . . ?
C10A C11A C12A C13A 1.2(2) . . . . ?
C11A C12A C13A C8A 0.0(2) . . . . ?
C13A C8A C9A C10A 0.75(18) . . . . ?
C14A C15A C16A C17A 171.88(11) . . . . ?
C14A C15A C20A C19A -174.46(11) . . . . ?
C15A C16A C17A C18A 3.49(18) . . . . ?
C16A C15A C20A C19A 1.11(18) . . . . ?
C16A C17A C18A N4A 179.79(11) . . . . ?
C16A C17A C18A C19A -0.75(19) . . . . ?
C17A C18A C19A C20A -1.79(19) . . . . ?
C18A C19A C20A C15A 1.58(19) . . . . ?
C20A C15A C16A C17A -3.70(18) . . . . ?
Cl1B C6B C7B N1B -177.67(8) . . . . ?
O1B N4B C18B C17B 1.84(17) . . . . ?
O1B N4B C18B C19B -177.16(11) . . . . ?
N1B C1B C2B N2B -2.30(12) . . . . ?
N1B C1B C2B C8B 173.40(11) . . . . ?
N1B C1B N3B C14B 164.58(11) . . . . ?
N1B C3B C4B C5B 1.36(16) . . . . ?
C1B N1B C3B N2B -1.23(12) . . . . ?
C1B N1B C3B C4B 178.90(10) . . . . ?
C1B N1B C7B C6B 179.74(11) . . . . ?
C1B C2B C8B C9B 156.72(12) . . . . ?
C1B C2B C8B C13B -30.08(18) . . . . ?
C1B N3B C14B C15B -177.81(10) . . . . ?
O2B N4B C18B C17B -178.88(11) . . . . ?
O2B N4B C18B C19B 2.12(17) . . . . ?
N2B C2B C8B C9B -27.87(15) . . . . ?
N2B C2B C8B C13B 145.33(11) . . . . ?
N2B C3B C4B C5B -178.48(11) . . . . ?
C2B C1B N3B C14B -11.2(2) . . . . ?
C2B N2B C3B N1B -0.21(12) . . . . ?
C2B N2B C3B C4B 179.64(11) . . . . ?
C2B C8B C9B C10B 173.16(11) . . . . ?
C2B C8B C13B C12B -174.05(11) . . . . ?
N3B C1B C2B N2B 173.78(13) . . . . ?
N3B C1B C2B C8B -10.5(2) . . . . ?
N3B C14B C15B C16B -174.16(11) . . . . ?
N3B C14B C15B C20B 7.02(17) . . . . ?
C3B N1B C1B C2B 2.08(12) . . . . ?
C3B N1B C1B N3B -175.12(9) . . . . ?
C3B N1B C7B C6B -1.08(17) . . . . ?
C3B N2B C2B C1B 1.59(12) . . . . ?
C3B N2B C2B C8B -174.70(10) . . . . ?
C3B C4B C5B C6B -0.77(17) . . . . ?
N4B C18B C19B C20B 178.61(11) . . . . ?
C4B C5B C6B Cl1B 178.56(9) . . . . ?
C4B C5B C6B C7B -0.80(19) . . . . ?
C5B C6B C7B N1B 1.70(18) . . . . ?
C7B N1B C1B C2B -178.64(11) . . . . ?
C7B N1B C1B N3B 4.16(17) . . . . ?
C7B N1B C3B N2B 179.43(10) . . . . ?
C7B N1B C3B C4B -0.44(16) . . . . ?
C8B C9B C10B C11B 1.17(19) . . . . ?
C9B C8B C13B C12B -0.89(17) . . . . ?
C9B C10B C11B C12B -0.9(2) . . . . ?
C10B C11B C12B C13B -0.3(2) . . . . ?
C11B C12B C13B C8B 1.18(18) . . . . ?
C13B C8B C9B C10B -0.29(17) . . . . ?
C14B C15B C16B C17B -179.50(11) . . . . ?
C14B C15B C20B C19B 178.16(11) . . . . ?
C15B C16B C17B C18B 1.45(18) . . . . ?
C16B C15B C20B C19B -0.67(18) . . . . ?
C16B C17B C18B N4B -179.91(10) . . . . ?
C16B C17B C18B C19B -0.96(18) . . . . ?
C17B C18B C19B C20B -0.34(18) . . . . ?
C18B C19B C20B C15B 1.16(18) . . . . ?
C20B C15B C16B C17B -0.67(17) . . . . ?
