#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/35/2243594.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_2243594
loop_
_publ_author_name
'Shaibah, Mohammed A. E.'
'Kavitha, Channappa N.'
'Yathirajan, Hemmige S.'
'Foro, Sabine'
'Glidewell, Christopher'
_publ_section_title
;
 A very short O---H···O hydrogen bond in the
 structure of clozapinium hydrogen bis(3,5-dinitrobenzoate)
;
_journal_coeditor_code           HB7944
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1629
_journal_page_last               1633
_journal_paper_doi               10.1107/S2056989020012268
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C18 H20 Cl N4 +, C7 H3 N2 O6 -, C7 H4 N2 O6'
_chemical_formula_moiety         'C18 H20 Cl N4 +, C7 H3 N2 O6 -, C7 H4 N2 O6'
_chemical_formula_sum            'C32 H27 Cl N8 O12'
_chemical_formula_weight         751.07
_chemical_name_common
;
Clozapinium hydrogen bis(3,5-dinitrobenzoate)
;
_chemical_name_systematic
;4-[6-Chloro-2,9-diazatricyclo[9.4.0.0^3,8^]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-10-yl]-1-methylpiperazin-1-ium
3,5-dinitrobenzoate--3,5-dinitrobenzic acid (1/1)
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 98.478(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4102(6)
_cell_length_b                   24.629(2)
_cell_length_c                   18.4460(10)
_cell_measurement_reflns_used    7183
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.885
_cell_measurement_theta_min      2.838
_cell_volume                     3329.7(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur Sapphire CCD detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13700
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.546
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       needle
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6870
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0452P)²+1.0626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                3811
_reflns_number_total             6870
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7944sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243594
_cod_database_fobs_code          2243594
_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   0.934
_shelx_estimated_absorpt_t_max   0.962
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3444(4) 0.23128(13) 0.08513(15) 0.0519(8) Uani d 1 . .
H H1 0.3445 0.1944 0.0957 0.062 Uiso calc 1 . .
C C2 0.2571(4) 0.24929(16) 0.01823(17) 0.0659(9) Uani d 1 . .
H H2 0.1993 0.2247 -0.0157 0.079 Uiso calc 1 . .
C C3 0.2559(4) 0.30335(16) 0.00210(16) 0.0650(9) Uani d 1 . .
H H3 0.2007 0.3155 -0.0436 0.078 Uiso calc 1 . .
C C4 0.3359(4) 0.33980(13) 0.05311(15) 0.0525(8) Uani d 1 . .
H H4 0.3326 0.3767 0.0421 0.063 Uiso calc 1 . .
C C4A 0.4220(3) 0.32228(11) 0.12132(13) 0.0383(6) Uani d 1 . .
N N5 0.5009(3) 0.36063(10) 0.17327(12) 0.0437(6) Uani d 1 . .
H H5 0.492(4) 0.3941(12) 0.1564(15) 0.052 Uiso d 1 . .
C C5A 0.4443(3) 0.35994(11) 0.24375(13) 0.0374(6) Uani d 1 . .
C C6 0.3781(4) 0.40729(12) 0.27020(15) 0.0458(7) Uani d 1 . .
H H6 0.3563 0.4371 0.2391 0.055 Uiso calc 1 . .
C C7 0.3434(4) 0.41167(13) 0.34144(16) 0.0519(8) Uani d 1 . .
H H7 0.3007 0.4440 0.3586 0.062 Uiso calc 1 . .
C C8 0.3733(4) 0.36715(13) 0.38635(15) 0.0487(7) Uani d 1 . .
Cl Cl8 0.34891(13) 0.37265(4) 0.47895(4) 0.0768(3) Uani d 1 . .
C C9 0.4298(3) 0.31860(12) 0.36041(14) 0.0463(7) Uani d 1 . .
H H9 0.4435 0.2884 0.3910 0.056 Uiso calc 1 . .
C C9A 0.4666(3) 0.31418(11) 0.28869(14) 0.0379(6) Uani d 1 . .
N N10 0.5458(3) 0.26494(9) 0.27155(11) 0.0410(5) Uani d 1 . .
C C11 0.5353(3) 0.24542(11) 0.20636(14) 0.0396(6) Uani d 1 . .
C C11A 0.4322(3) 0.26698(11) 0.13697(13) 0.0391(6) Uani d 1 . .
N N11 0.6093(3) 0.19388(9) 0.20017(11) 0.0451(6) Uani d 1 . .
C C12 0.6660(4) 0.16212(12) 0.26609(15) 0.0524(8) Uani d 1 . .
H H12A 0.6413 0.1241 0.2553 0.063 Uiso calc 1 . .
H H12B 0.5939 0.1729 0.3035 0.063 Uiso calc 1 . .
C C13 0.8645(4) 0.16879(12) 0.29558(15) 0.0524(8) Uani d 1 . .
H H13A 0.8889 0.2062 0.3105 0.063 Uiso calc 1 . .
H H13B 0.8964 0.1457 0.3382 0.063 Uiso calc 1 . .
N N14 0.9768(3) 0.15369(10) 0.23769(13) 0.0472(6) Uani d 1 . .
H H14 0.947(4) 0.1154(12) 0.2223(14) 0.057 Uiso d 1 . .
C C15 0.9216(4) 0.18776(12) 0.17106(15) 0.0508(7) Uani d 1 . .
H H15A 0.9913 0.1769 0.1329 0.061 Uiso calc 1 . .
H H15B 0.9492 0.2255 0.1828 0.061 Uiso calc 1 . .
C C16 0.7201(4) 0.18191(12) 0.14324(15) 0.0471(7) Uani d 1 . .
H H16A 0.6868 0.2064 0.1023 0.057 Uiso calc 1 . .
H H16B 0.6954 0.1451 0.1257 0.057 Uiso calc 1 . .
C C17 1.1766(4) 0.15711(16) 0.2639(2) 0.0800(11) Uani d 1 . .
H H17A 1.2074 0.1934 0.2803 0.120 Uiso calc 1 . .
H H17B 1.2425 0.1480 0.2245 0.120 Uiso calc 1 . .
H H17C 1.2086 0.1322 0.3037 0.120 Uiso calc 1 . .
C C21 0.2811(4) 0.54057(11) 0.01705(14) 0.0419(7) Uani d 1 . .
C C22 0.2657(4) 0.59602(12) 0.00575(16) 0.0492(7) Uani d 1 . .
H H22 0.3254 0.6201 0.0400 0.059 Uiso calc 1 . .
C C23 0.1607(4) 0.61492(13) -0.05705(17) 0.0535(8) Uani d 1 . .
C C24 0.0736(4) 0.58098(14) -0.11005(17) 0.0572(8) Uani d 1 . .
H H24 0.0046 0.5945 -0.1524 0.069 Uiso calc 1 . .
C C25 0.0928(4) 0.52651(13) -0.09794(15) 0.0484(7) Uani d 1 . .
C C26 0.1939(4) 0.50581(12) -0.03532(15) 0.0456(7) Uani d 1 . .
H H26 0.2033 0.4684 -0.0284 0.055 Uiso calc 1 . .
C C27 0.3916(4) 0.51740(13) 0.08452(16) 0.0473(7) Uani d 1 . .
O O21 0.3873(3) 0.46873(9) 0.09583(11) 0.0678(6) Uani d 1 . .
O O22 0.4857(3) 0.55163(8) 0.12759(12) 0.0570(6) Uani d 1 . .
H H22A 0.572(5) 0.5330(14) 0.1755(19) 0.085 Uiso d 1 . .
N N23 0.1434(5) 0.67388(13) -0.0680(2) 0.0740(9) Uani d 1 . .
O O23 0.2158(4) 0.70360(11) -0.0192(2) 0.1043(10) Uani d 1 . .
O O24 0.0524(5) 0.68988(11) -0.12377(16) 0.1095(10) Uani d 1 . .
N N25 -0.0005(4) 0.48816(15) -0.15269(16) 0.0669(8) Uani d 1 . .
O O25 0.0063(4) 0.44003(12) -0.13688(13) 0.0836(8) Uani d 1 . .
O O26 -0.0774(3) 0.50674(12) -0.21036(14) 0.0935(9) Uani d 1 . .
C C31 0.7597(4) 0.47059(12) 0.34692(15) 0.0446(7) Uani d 1 . .
C C32 0.8228(4) 0.42264(12) 0.32110(15) 0.0463(7) Uani d 1 . .
H H32 0.8254 0.4179 0.2713 0.056 Uiso calc 1 . .
C C33 0.8817(4) 0.38203(11) 0.37005(15) 0.0447(7) Uani d 1 . .
C C34 0.8818(4) 0.38730(12) 0.44445(16) 0.0496(7) Uani d 1 . .
H H34 0.9216 0.3594 0.4769 0.060 Uiso calc 1 . .
C C35 0.8204(4) 0.43570(12) 0.46830(15) 0.0503(7) Uani d 1 . .
C C36 0.7589(4) 0.47737(12) 0.42137(15) 0.0505(7) Uani d 1 . .
H H36 0.7173 0.5096 0.4394 0.061 Uiso calc 1 . .
C C37 0.6800(4) 0.51417(14) 0.29415(17) 0.0507(8) Uani d 1 . .
O O31 0.6202(3) 0.55554(9) 0.31888(12) 0.0689(6) Uani d 1 . .
O O32 0.6772(3) 0.50299(9) 0.22654(12) 0.0653(6) Uani d 1 . .
N N33 0.9440(3) 0.33021(11) 0.34261(16) 0.0565(7) Uani d 1 . .
O O33 0.9549(3) 0.32681(10) 0.27753(13) 0.0774(7) Uani d 1 . .
O O34 0.9802(4) 0.29336(9) 0.38628(13) 0.0768(7) Uani d 1 . .
N N35 0.8168(5) 0.44262(13) 0.54739(15) 0.0740(9) Uani d 0.44(3) A 1
O O35 0.830(4) 0.4023(5) 0.5865(10) 0.086(5) Uani d 0.44(3) A 1
O O36 0.816(3) 0.4907(3) 0.5686(6) 0.078(3) Uani d 0.44(3) A 1
N N45 0.8168(5) 0.44262(13) 0.54739(15) 0.0740(9) Uani d 0.56(3) A 2
O O45 0.900(2) 0.4100(6) 0.5902(8) 0.084(4) Uani d 0.56(3) A 2
O O46 0.712(3) 0.4787(6) 0.5660(5) 0.098(4) Uani d 0.56(3) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C11A . . 121.5(3) ?
C2 C1 H1 . . 119.2 ?
C11A C1 H1 . . 119.2 ?
C3 C2 C1 . . 119.8(3) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 120.1(3) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C4A . . 120.8(3) ?
C3 C4 H4 . . 119.6 ?
C4A C4 H4 . . 119.6 ?
C11A C4A C4 . . 119.6(3) ?
C11A C4A N5 . . 120.7(2) ?
C4 C4A N5 . . 119.7(3) ?
C4A N5 C5A . . 117.7(2) ?
C4A N5 H5 . . 112.6(18) ?
C5A N5 H5 . . 108.5(18) ?
C6 C5A C9A . . 119.3(2) ?
C6 C5A N5 . . 118.7(2) ?
C9A C5A N5 . . 121.8(2) ?
C7 C6 C5A . . 121.9(3) ?
C7 C6 H6 . . 119.1 ?
C5A C6 H6 . . 119.1 ?
C8 C7 C6 . . 118.4(3) ?
C8 C7 H7 . . 120.8 ?
C6 C7 H7 . . 120.8 ?
C7 C8 C9 . . 121.0(3) ?
C7 C8 Cl8 . . 119.8(2) ?
C9 C8 Cl8 . . 119.2(2) ?
C8 C9 C9A . . 120.7(3) ?
C8 C9 H9 . . 119.7 ?
C9A C9 H9 . . 119.7 ?
C9 C9A C5A . . 118.6(3) ?
C9 C9A N10 . . 115.3(2) ?
C5A C9A N10 . . 125.5(2) ?
C11 N10 C9A . . 124.3(2) ?
N10 C11 N11 . . 116.5(2) ?
N10 C11 C11A . . 128.5(2) ?
N11 C11 C11A . . 114.4(2) ?
C1 C11A C4A . . 118.1(2) ?
C1 C11A C11 . . 119.7(3) ?
C4A C11A C11 . . 122.2(2) ?
C11 N11 C12 . . 119.3(2) ?
C11 N11 C16 . . 120.9(2) ?
C12 N11 C16 . . 111.7(2) ?
N11 C12 C13 . . 113.0(2) ?
N11 C12 H12A . . 109.0 ?
C13 C12 H12A . . 109.0 ?
N11 C12 H12B . . 109.0 ?
C13 C12 H12B . . 109.0 ?
H12A C12 H12B . . 107.8 ?
N14 C13 C12 . . 109.5(2) ?
N14 C13 H13A . . 109.8 ?
C12 C13 H13A . . 109.8 ?
N14 C13 H13B . . 109.8 ?
C12 C13 H13B . . 109.8 ?
H13A C13 H13B . . 108.2 ?
C17 N14 C13 . . 112.7(2) ?
C17 N14 C15 . . 111.9(2) ?
C13 N14 C15 . . 109.5(2) ?
C17 N14 H14 . . 108.2(16) ?
C13 N14 H14 . . 108.3(16) ?
C15 N14 H14 . . 105.9(15) ?
N14 C15 C16 . . 111.3(2) ?
N14 C15 H15A . . 109.4 ?
C16 C15 H15A . . 109.4 ?
N14 C15 H15B . . 109.4 ?
C16 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
N11 C16 C15 . . 111.7(2) ?
N11 C16 H16A . . 109.3 ?
C15 C16 H16A . . 109.3 ?
N11 C16 H16B . . 109.3 ?
C15 C16 H16B . . 109.3 ?
H16A C16 H16B . . 107.9 ?
N14 C17 H17A . . 109.5 ?
N14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C26 C21 C22 . . 119.2(3) ?
C26 C21 C27 . . 119.2(3) ?
C22 C21 C27 . . 121.6(3) ?
C23 C22 C21 . . 118.9(3) ?
C23 C22 H22 . . 120.5 ?
C21 C22 H22 . . 120.5 ?
C24 C23 C22 . . 122.7(3) ?
C24 C23 N23 . . 118.8(3) ?
C22 C23 N23 . . 118.5(3) ?
C25 C24 C23 . . 117.1(3) ?
C25 C24 H24 . . 121.4 ?
C23 C24 H24 . . 121.4 ?
C24 C25 C26 . . 122.1(3) ?
C24 C25 N25 . . 119.3(3) ?
C26 C25 N25 . . 118.5(3) ?
C21 C26 C25 . . 119.9(3) ?
C21 C26 H26 . . 120.1 ?
C25 C26 H26 . . 120.1 ?
O21 C27 O22 . . 124.3(3) ?
O21 C27 C21 . . 119.5(3) ?
O22 C27 C21 . . 116.2(3) ?
C27 O22 H22A . . 114.6(17) ?
O24 N23 O23 . . 124.1(3) ?
O24 N23 C23 . . 117.7(4) ?
O23 N23 C23 . . 118.1(3) ?
O26 N25 O25 . . 124.8(3) ?
O26 N25 C25 . . 117.9(3) ?
O25 N25 C25 . . 117.3(3) ?
C32 C31 C36 . . 119.8(3) ?
C32 C31 C37 . . 120.4(3) ?
C36 C31 C37 . . 119.7(3) ?
C33 C32 C31 . . 119.1(3) ?
C33 C32 H32 . . 120.4 ?
C31 C32 H32 . . 120.4 ?
C32 C33 C34 . . 122.6(3) ?
C32 C33 N33 . . 119.4(3) ?
C34 C33 N33 . . 118.0(3) ?
C35 C34 C33 . . 116.7(3) ?
C35 C34 H34 . . 121.6 ?
C33 C34 H34 . . 121.6 ?
C34 C35 C36 . . 122.8(3) ?
C34 C35 N35 . . 118.3(3) ?
C36 C35 N35 . . 119.0(3) ?
C35 C36 C31 . . 119.0(3) ?
C35 C36 H36 . . 120.5 ?
C31 C36 H36 . . 120.5 ?
O31 C37 O32 . . 126.1(3) ?
O31 C37 C31 . . 118.7(3) ?
O32 C37 C31 . . 115.2(3) ?
C37 O32 H22A . . 119.2(14) ?
O34 N33 O33 . . 124.1(3) ?
O34 N33 C33 . . 118.0(3) ?
O33 N33 C33 . . 117.9(3) ?
O35 N35 O36 . . 126.1(11) ?
O35 N35 C35 . . 118.6(11) ?
O36 N35 C35 . . 115.0(7) ?
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
C1 C2 . 1.380(4) ?
C1 C11A . 1.388(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.364(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.371(4) ?
C3 H3 . 0.9300 ?
C4 C4A . 1.393(4) ?
C4 H4 . 0.9300 ?
C4A C11A . 1.392(4) ?
C4A N5 . 1.410(3) ?
N5 C5A . 1.424(3) ?
N5 H5 . 0.88(3) ?
C5A C6 . 1.382(4) ?
C5A C9A . 1.394(4) ?
C6 C7 . 1.380(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.372(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.376(4) ?
C8 Cl8 . 1.749(3) ?
C9 C9A . 1.394(4) ?
C9 H9 . 0.9300 ?
C9A N10 . 1.404(3) ?
N10 C11 . 1.287(3) ?
C11 N11 . 1.394(3) ?
C11 C11A . 1.489(4) ?
N11 C12 . 1.455(3) ?
N11 C16 . 1.455(3) ?
C12 C13 . 1.500(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 N14 . 1.494(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
N14 C17 . 1.490(4) ?
N14 C15 . 1.495(3) ?
N14 H14 . 1.00(3) ?
C15 C16 . 1.512(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C21 C26 . 1.378(4) ?
C21 C22 . 1.384(4) ?
C21 C27 . 1.498(4) ?
C22 C23 . 1.378(4) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.373(4) ?
C23 N23 . 1.469(4) ?
C24 C25 . 1.364(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.379(4) ?
C25 N25 . 1.478(4) ?
C26 H26 . 0.9300 ?
C27 O21 . 1.218(3) ?
C27 O22 . 1.290(3) ?
O22 H22A . 1.11(4) ?
N23 O24 . 1.210(4) ?
N23 O23 . 1.221(4) ?
N25 O26 . 1.220(3) ?
N25 O25 . 1.220(4) ?
C31 C32 . 1.380(4) ?
C31 C36 . 1.384(4) ?
C31 C37 . 1.510(4) ?
C32 C33 . 1.375(4) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.378(4) ?
C33 N33 . 1.472(4) ?
C34 C35 . 1.372(4) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.376(4) ?
C35 N35 . 1.473(4) ?
C36 H36 . 0.9300 ?
C37 O31 . 1.226(4) ?
C37 O32 . 1.274(3) ?
O32 H22A . 1.35(4) ?
N33 O34 . 1.217(3) ?
N33 O33 . 1.218(3) ?
N35 O35 . 1.224(8) ?
N35 O36 . 1.249(6) ?
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
_geom_hbond_publ_flag
N5 H5 O21 . 0.88(3) 2.23(3) 3.079(3) 162(3) y
O22 H22A O32 . 1.11(4) 1.35(4) 2.453(3) 169(3) y
C4 H4 O21 . 0.93 2.48 3.280(4) 144 y
C13 H13A O34 . 0.97 2.60 3.539(4) 164 y
N14 H14 O31 2_645 1.00(3) 1.70(3) 2.689(3) 169(3) y
C1 H1 O35 4_565 0.93 2.39 3.292(13) 164 y
C7 H7 O36 3_666 0.93 2.34 3.242(13) 163 y
C7 H7 O46 3_666 0.93 2.37 3.253(14) 159 y
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
C11A C1 C2 C3 . . . . -0.1(5) ?
C1 C2 C3 C4 . . . . -2.2(5) ?
C2 C3 C4 C4A . . . . 1.1(5) ?
C3 C4 C4A C11A . . . . 2.1(4) ?
C3 C4 C4A N5 . . . . -179.0(3) ?
C11A C4A N5 C5A . . . . -56.2(3) ?
C4 C4A N5 C5A . . . . 125.0(3) ?
C4A N5 C5A C6 . . . . -125.3(3) ?
C4A N5 C5A C9A . . . . 59.5(3) ?
C9A C5A C6 C7 . . . . 3.9(4) ?
N5 C5A C6 C7 . . . . -171.3(2) ?
C5A C6 C7 C8 . . . . -1.0(4) ?
C6 C7 C8 C9 . . . . -2.5(4) ?
C6 C7 C8 Cl8 . . . . 174.8(2) ?
C7 C8 C9 C9A . . . . 3.2(4) ?
Cl8 C8 C9 C9A . . . . -174.1(2) ?
C8 C9 C9A C5A . . . . -0.3(4) ?
C8 C9 C9A N10 . . . . 172.0(2) ?
C6 C5A C9A C9 . . . . -3.2(4) ?
N5 C5A C9A C9 . . . . 171.9(2) ?
C6 C5A C9A N10 . . . . -174.5(2) ?
N5 C5A C9A N10 . . . . 0.6(4) ?
C9 C9A N10 C11 . . . . 155.9(2) ?
C5A C9A N10 C11 . . . . -32.5(4) ?
C9A N10 C11 N11 . . . . -174.9(2) ?
C9A N10 C11 C11A . . . . -4.2(4) ?
C2 C1 C11A C4A . . . . 3.3(4) ?
C2 C1 C11A C11 . . . . -175.9(3) ?
C4 C4A C11A C1 . . . . -4.2(4) ?
N5 C4A C11A C1 . . . . 176.9(2) ?
C4 C4A C11A C11 . . . . 174.9(2) ?
N5 C4A C11A C11 . . . . -3.9(4) ?
N10 C11 C11A C1 . . . . -141.2(3) ?
N11 C11 C11A C1 . . . . 29.6(3) ?
N10 C11 C11A C4A . . . . 39.7(4) ?
N11 C11 C11A C4A . . . . -149.5(2) ?
N10 C11 N11 C12 . . . . 9.7(4) ?
C11A C11 N11 C12 . . . . -162.3(2) ?
N10 C11 N11 C16 . . . . -136.6(3) ?
C11A C11 N11 C16 . . . . 51.4(3) ?
C11 N11 C12 C13 . . . . -94.0(3) ?
C16 N11 C12 C13 . . . . 55.2(3) ?
N11 C12 C13 N14 . . . . -57.1(3) ?
C12 C13 N14 C17 . . . . -177.7(3) ?
C12 C13 N14 C15 . . . . 57.1(3) ?
C17 N14 C15 C16 . . . . 177.5(3) ?
C13 N14 C15 C16 . . . . -56.8(3) ?
C11 N11 C16 C15 . . . . 95.5(3) ?
C12 N11 C16 C15 . . . . -53.1(3) ?
N14 C15 C16 N11 . . . . 54.9(3) ?
C26 C21 C22 C23 . . . . 1.2(4) ?
C27 C21 C22 C23 . . . . -179.4(2) ?
C21 C22 C23 C24 . . . . -1.6(4) ?
C21 C22 C23 N23 . . . . 179.2(2) ?
C22 C23 C24 C25 . . . . 0.8(4) ?
N23 C23 C24 C25 . . . . -179.9(3) ?
C23 C24 C25 C26 . . . . 0.3(4) ?
C23 C24 C25 N25 . . . . 179.0(2) ?
C22 C21 C26 C25 . . . . -0.1(4) ?
C27 C21 C26 C25 . . . . -179.6(2) ?
C24 C25 C26 C21 . . . . -0.7(4) ?
N25 C25 C26 C21 . . . . -179.4(2) ?
C26 C21 C27 O21 . . . . -7.7(4) ?
C22 C21 C27 O21 . . . . 172.9(3) ?
C26 C21 C27 O22 . . . . 172.8(2) ?
C22 C21 C27 O22 . . . . -6.7(4) ?
C24 C23 N23 O24 . . . . -0.1(4) ?
C22 C23 N23 O24 . . . . 179.2(3) ?
C24 C23 N23 O23 . . . . 177.3(3) ?
C22 C23 N23 O23 . . . . -3.4(4) ?
C24 C25 N25 O26 . . . . 6.9(4) ?
C26 C25 N25 O26 . . . . -174.3(3) ?
C24 C25 N25 O25 . . . . -173.5(3) ?
C26 C25 N25 O25 . . . . 5.3(4) ?
C36 C31 C32 C33 . . . . 0.8(4) ?
C37 C31 C32 C33 . . . . -175.0(2) ?
C31 C32 C33 C34 . . . . -0.5(4) ?
C31 C32 C33 N33 . . . . 178.2(2) ?
C32 C33 C34 C35 . . . . -0.3(4) ?
N33 C33 C34 C35 . . . . -179.0(3) ?
C33 C34 C35 C36 . . . . 0.8(5) ?
C33 C34 C35 N35 . . . . 179.4(3) ?
C34 C35 C36 C31 . . . . -0.4(5) ?
N35 C35 C36 C31 . . . . -179.1(3) ?
C32 C31 C36 C35 . . . . -0.4(4) ?
C37 C31 C36 C35 . . . . 175.5(3) ?
C32 C31 C37 O31 . . . . 177.8(3) ?
C36 C31 C37 O31 . . . . 1.9(4) ?
C32 C31 C37 O32 . . . . -0.2(4) ?
C36 C31 C37 O32 . . . . -176.1(3) ?
C32 C33 N33 O34 . . . . -173.7(3) ?
C34 C33 N33 O34 . . . . 5.0(4) ?
C32 C33 N33 O33 . . . . 5.9(4) ?
C34 C33 N33 O33 . . . . -175.4(3) ?
C34 C35 N35 O35 . . . . -15.5(15) ?
C36 C35 N35 O35 . . . . 163.2(15) ?
C34 C35 N35 O36 . . . . 158.5(11) ?
C36 C35 N35 O36 . . . . -22.8(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168326820
