#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:08:36 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290150 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/79/7247961.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_7247961
loop_
_publ_author_name
'Nechipadappu, Sunil Kumar'
'Swain, Debasish'
_publ_section_title
;
 New drug--drug and drug--nutraceutical salts of anti-emetic drug
 domperidone: structural and physicochemical aspects of new salts
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              926
_journal_page_last               942
_journal_paper_doi               10.1039/D3CE01000G
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C22 H25 Cl N5 O2 1+, C5 H3 N2 O4 1-'
_chemical_formula_sum            'C27 H28 Cl N7 O6'
_chemical_formula_weight         582.01
_chemical_name_common            'Domperidone orotate'
_chemical_name_systematic        'Domperidone orotate'
_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   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-09-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                99.679(2)
_cell_angle_beta                 102.801(2)
_cell_angle_gamma                91.935(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5379(4)
_cell_length_b                   11.3926(6)
_cell_length_c                   15.8690(8)
_cell_measurement_reflns_used    3380
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.02
_cell_measurement_theta_min      2.44
_cell_volume                     1306.40(12)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_unetI/netI     0.1273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25326
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.352
_diffrn_reflns_theta_min         2.676
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.1688
_refine_ls_R_factor_gt           0.0545
_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)+(0.0642P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2721
_reflns_number_total             6485
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01000g2.cif
_cod_data_source_block           KB546_0m
_cod_depositor_comments
'Adding full bibliography for 7247958--7247965.cif.'
_cod_database_code               7247961
_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   0.982
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C -0.1504(4) 0.4655(3) 0.06593(19) 0.0424(7) Uani 1 1 d . . . . .
C2 C -0.1939(4) 0.3719(3) -0.00559(17) 0.0412(7) Uani 1 1 d . . . . .
H2 H -0.298657 0.369125 -0.049962 0.049 Uiso 1 1 calc R U . . .
C3 C -0.0736(4) 0.2836(2) -0.00720(17) 0.0374(7) Uani 1 1 d . . . . .
C4 C 0.0826(4) 0.2853(2) 0.06015(17) 0.0360(7) Uani 1 1 d . . . . .
C5 C 0.1258(4) 0.3799(2) 0.12981(17) 0.0419(7) Uani 1 1 d . . . . .
H5A H 0.230878 0.383168 0.174102 0.050 Uiso 1 1 calc R U . . .
C6 C 0.0065(4) 0.4699(2) 0.13117(17) 0.0419(7) Uani 1 1 d . . . . .
H6A H 0.032799 0.534834 0.177194 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0763(4) 0.1206(3) -0.04352(19) 0.0447(8) Uani 1 1 d . . . . .
C8 C 0.3423(4) 0.1477(2) 0.08574(17) 0.0406(7) Uani 1 1 d . . . . .
H8 H 0.365872 0.070808 0.053455 0.049 Uiso 1 1 calc R U . . .
C9 C 0.3297(4) 0.1285(3) 0.17729(17) 0.0442(7) Uani 1 1 d . . . . .
H9A H 0.285788 0.199082 0.207224 0.053 Uiso 1 1 calc R U . . .
H9B H 0.241812 0.061862 0.171628 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5112(4) 0.1038(2) 0.23234(18) 0.0448(8) Uani 1 1 d . . . . .
H10A H 0.498321 0.097755 0.290958 0.054 Uiso 1 1 calc R U . . .
H10B H 0.549304 0.028424 0.206339 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6766(4) 0.2095(2) 0.14744(16) 0.0403(7) Uani 1 1 d . . . . .
H11A H 0.716075 0.134533 0.121478 0.048 Uiso 1 1 calc R U . . .
H11B H 0.770406 0.271941 0.151489 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5008(4) 0.2361(3) 0.08954(16) 0.0414(7) Uani 1 1 d . . . . .
H12A H 0.517942 0.234468 0.030568 0.050 Uiso 1 1 calc R U . . .
H12B H 0.470799 0.315865 0.111436 0.050 Uiso 1 1 calc R U . . .
C13 C 0.8293(4) 0.1887(2) 0.29922(18) 0.0425(7) Uani 1 1 d . . . . .
H13A H 0.901844 0.136181 0.268284 0.051 Uiso 1 1 calc R U . . .
H13B H 0.805338 0.152596 0.347119 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9359(4) 0.3088(2) 0.33623(17) 0.0426(7) Uani 1 1 d . . . . .
H14A H 0.935610 0.352382 0.288685 0.051 Uiso 1 1 calc R U . . .
H14B H 0.875306 0.354730 0.377309 0.051 Uiso 1 1 calc R U . . .
C15 C 1.1320(4) 0.2974(2) 0.38271(17) 0.0415(7) Uani 1 1 d . . . . .
H15A H 1.199770 0.267867 0.339210 0.050 Uiso 1 1 calc R U . . .
H15B H 1.186829 0.375950 0.412503 0.050 Uiso 1 1 calc R U . . .
C16 C 1.2070(4) 0.1052(2) 0.43270(19) 0.0389(7) Uani 1 1 d . . . . .
C17 C 1.1626(4) 0.1470(2) 0.57070(17) 0.0381(7) Uani 1 1 d . . . . .
C18 C 1.1498(4) 0.1461(3) 0.65553(19) 0.0500(8) Uani 1 1 d . . . . .
H18 H 1.178268 0.080352 0.682231 0.060 Uiso 1 1 calc R U . . .
C19 C 1.0925(4) 0.2477(3) 0.6992(2) 0.0561(9) Uani 1 1 d . . . . .
H19 H 1.080874 0.249739 0.756555 0.067 Uiso 1 1 calc R U . . .
C20 C 1.0519(4) 0.3461(3) 0.6607(2) 0.0536(9) Uani 1 1 d . . . . .
H20 H 1.016486 0.413564 0.692797 0.064 Uiso 1 1 calc R U . . .
C21 C 1.0631(4) 0.3460(3) 0.57498(19) 0.0481(8) Uani 1 1 d . . . . .
H21 H 1.033365 0.411526 0.548172 0.058 Uiso 1 1 calc R U . . .
C22 C 1.1199(4) 0.2452(2) 0.53091(16) 0.0344(7) Uani 1 1 d . . . . .
Cl1 Cl -0.29487(12) 0.58001(7) 0.07345(5) 0.0615(3) Uani 1 1 d . . . . .
N1 N -0.0742(4) 0.1818(2) -0.06868(18) 0.0472(7) Uani 1 1 d . . . . .
H1N H -0.150(4) 0.167(3) -0.1154(19) 0.052(10) Uiso 1 1 d . . . . .
N2 N 0.1714(3) 0.18327(19) 0.03716(14) 0.0399(6) Uani 1 1 d . . . . .
N3 N 0.6525(3) 0.2018(2) 0.23774(13) 0.0337(6) Uani 1 1 d . . . . .
H3N H 0.601(4) 0.273(3) 0.2563(17) 0.055(9) Uiso 1 1 d . . . . .
N4 N 1.1481(3) 0.21817(18) 0.44630(13) 0.0372(6) Uani 1 1 d . . . . .
N5 N 1.2155(3) 0.0614(2) 0.50881(15) 0.0433(7) Uani 1 1 d . . . . .
H5N H 1.255(6) -0.012(4) 0.510(2) 0.116(15) Uiso 1 1 d . . . . .
O1 O 0.1195(3) 0.02919(19) -0.08400(13) 0.0653(7) Uani 1 1 d . . . . .
O2 O 1.2417(3) 0.05405(16) 0.36390(12) 0.0499(6) Uani 1 1 d . . . . .
C23 C 0.5304(4) 0.4750(2) 0.3552(2) 0.0383(7) Uani 1 1 d . . . . .
C24 C 0.4640(4) 0.5993(2) 0.35197(17) 0.0332(7) Uani 1 1 d . . . . .
C25 C 0.4409(4) 0.6474(2) 0.27930(17) 0.0362(7) Uani 1 1 d . . . . .
H25 H 0.460494 0.603013 0.227798 0.043 Uiso 1 1 calc R U . . .
C26 C 0.3862(4) 0.7668(2) 0.28027(18) 0.0377(7) Uani 1 1 d . . . . .
C27 C 0.3781(4) 0.7753(2) 0.43522(18) 0.0373(7) Uani 1 1 d . . . . .
O3 O 0.5164(3) 0.40946(17) 0.28169(13) 0.0603(6) Uani 1 1 d . . . . .
O4 O 0.5951(3) 0.45059(17) 0.42789(13) 0.0582(6) Uani 1 1 d . . . . .
O5 O 0.3613(3) 0.81876(17) 0.21700(12) 0.0514(6) Uani 1 1 d . . . . .
O6 O 0.3485(3) 0.83138(16) 0.50323(12) 0.0485(6) Uani 1 1 d . . . . .
N6 N 0.4333(3) 0.66168(19) 0.42817(15) 0.0357(6) Uani 1 1 d . . . . .
H6N H 0.445(4) 0.630(3) 0.4769(19) 0.058(10) Uiso 1 1 d . . . . .
N7 N 0.3609(3) 0.8224(2) 0.36002(15) 0.0380(6) Uani 1 1 d . . . . .
H7N H 0.325(4) 0.885(2) 0.3612(15) 0.027(8) 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 0.0033 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'
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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 121.5(2) . . ?
C6 C1 Cl1 119.0(2) . . ?
C2 C1 Cl1 119.5(2) . . ?
C3 C2 C1 116.5(3) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C2 C3 N1 130.9(3) . . ?
C2 C3 C4 122.4(3) . . ?
N1 C3 C4 106.7(3) . . ?
C5 C4 N2 132.6(3) . . ?
C5 C4 C3 120.4(2) . . ?
N2 C4 C3 106.9(2) . . ?
C4 C5 C6 117.4(3) . . ?
C4 C5 H5A 121.3 . . ?
C6 C5 H5A 121.3 . . ?
C1 C6 C5 121.7(3) . . ?
C1 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
O1 C7 N1 127.2(3) . . ?
O1 C7 N2 126.4(3) . . ?
N1 C7 N2 106.3(3) . . ?
N2 C8 C12 111.2(2) . . ?
N2 C8 C9 111.7(2) . . ?
C12 C8 C9 111.7(2) . . ?
N2 C8 H8 107.3 . . ?
C12 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C10 C9 C8 112.6(2) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N3 C10 C9 110.3(2) . . ?
N3 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N3 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N3 C11 C12 110.9(2) . . ?
N3 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C8 112.8(2) . . ?
C11 C12 H12A 109.0 . . ?
C8 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C8 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 C14 111.3(2) . . ?
N3 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 112.9(2) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N4 C15 C14 113.3(2) . . ?
N4 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
N4 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 N5 127.6(2) . . ?
O2 C16 N4 125.5(3) . . ?
N5 C16 N4 106.9(2) . . ?
C18 C17 C22 121.6(2) . . ?
C18 C17 N5 131.7(3) . . ?
C22 C17 N5 106.7(2) . . ?
C17 C18 C19 116.7(3) . . ?
C17 C18 H18 121.7 . . ?
C19 C18 H18 121.7 . . ?
C20 C19 C18 122.1(3) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 117.4(3) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C21 C22 C17 121.3(2) . . ?
C21 C22 N4 131.3(2) . . ?
C17 C22 N4 107.4(2) . . ?
C7 N1 C3 110.6(3) . . ?
C7 N1 H1N 127(2) . . ?
C3 N1 H1N 122(2) . . ?
C7 N2 C4 109.4(2) . . ?
C7 N2 C8 123.3(2) . . ?
C4 N2 C8 127.2(2) . . ?
C10 N3 C13 112.5(2) . . ?
C10 N3 C11 109.8(2) . . ?
C13 N3 C11 112.0(2) . . ?
C10 N3 H3N 105.2(17) . . ?
C13 N3 H3N 111.7(17) . . ?
C11 N3 H3N 105.2(16) . . ?
C16 N4 C22 109.4(2) . . ?
C16 N4 C15 123.8(2) . . ?
C22 N4 C15 126.7(2) . . ?
C16 N5 C17 109.6(2) . . ?
C16 N5 H5N 117(2) . . ?
C17 N5 H5N 134(2) . . ?
O4 C23 O3 127.2(2) . . ?
O4 C23 C24 117.6(2) . . ?
O3 C23 C24 115.1(3) . . ?
C25 C24 N6 121.0(2) . . ?
C25 C24 C23 122.3(2) . . ?
N6 C24 C23 116.7(2) . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
O5 C26 N7 120.6(2) . . ?
O5 C26 C25 125.3(2) . . ?
N7 C26 C25 114.1(3) . . ?
O6 C27 N6 123.1(2) . . ?
O6 C27 N7 122.5(2) . . ?
N6 C27 N7 114.3(2) . . ?
C24 N6 C27 122.8(2) . . ?
C24 N6 H6N 122.1(18) . . ?
C27 N6 H6N 115.0(18) . . ?
C27 N7 C26 127.3(3) . . ?
C27 N7 H7N 116.6(18) . . ?
C26 N7 H7N 115.9(18) . . ?
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
C1 C6 1.382(4) . ?
C1 C2 1.392(4) . ?
C1 Cl1 1.733(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 N1 1.384(3) . ?
C3 C4 1.401(4) . ?
C4 C5 1.381(3) . ?
C4 N2 1.396(3) . ?
C5 C6 1.387(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 O1 1.222(3) . ?
C7 N1 1.371(4) . ?
C7 N2 1.383(3) . ?
C8 N2 1.456(3) . ?
C8 C12 1.520(4) . ?
C8 C9 1.527(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.514(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.495(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.500(3) . ?
C11 C12 1.508(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.495(3) . ?
C13 C14 1.519(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.519(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.452(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.234(3) . ?
C16 N5 1.372(3) . ?
C16 N4 1.373(3) . ?
C17 C18 1.372(4) . ?
C17 C22 1.388(4) . ?
C17 N5 1.397(3) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C22 N4 1.391(3) . ?
N1 H1N 0.82(3) . ?
N3 H3N 0.94(3) . ?
N5 H5N 0.90(4) . ?
C23 O4 1.231(3) . ?
C23 O3 1.255(3) . ?
C23 C24 1.522(4) . ?
C24 C25 1.338(3) . ?
C24 N6 1.366(3) . ?
C25 C26 1.434(4) . ?
C25 H25 0.9300 . ?
C26 O5 1.231(3) . ?
C26 N7 1.373(3) . ?
C27 O6 1.228(3) . ?
C27 N6 1.367(3) . ?
C27 N7 1.371(3) . ?
N6 H6N 0.90(3) . ?
N7 H7N 0.77(2) . ?
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
N1 H1N O5 0.82(3) 2.03(3) 2.821(4) 162(3) 2_565 yes
N5 H5N O6 0.90(4) 1.94(4) 2.832(3) 175(4) 1_645 yes
N6 H6N O4 0.90(3) 1.97(3) 2.843(3) 166(3) 2_666 yes
N7 H7N O2 0.77(2) 2.05(3) 2.811(3) 177(3) 1_465 yes
N3 H3N O3 0.94(3) 1.72(3) 2.658(3) 174(2) . 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
C6 C1 C2 C3 0.7(4) . . . . ?
Cl1 C1 C2 C3 -179.7(2) . . . . ?
C1 C2 C3 N1 -178.3(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C2 C3 C4 C5 -2.8(4) . . . . ?
N1 C3 C4 C5 177.0(2) . . . . ?
C2 C3 C4 N2 179.9(2) . . . . ?
N1 C3 C4 N2 -0.3(3) . . . . ?
N2 C4 C5 C6 178.3(3) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
Cl1 C1 C6 C5 178.7(2) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
N2 C8 C9 C10 -174.1(2) . . . . ?
C12 C8 C9 C10 -48.8(3) . . . . ?
C8 C9 C10 N3 55.4(3) . . . . ?
N3 C11 C12 C8 -54.4(3) . . . . ?
N2 C8 C12 C11 173.8(2) . . . . ?
C9 C8 C12 C11 48.2(3) . . . . ?
N3 C13 C14 C15 -167.5(2) . . . . ?
C13 C14 C15 N4 -49.9(3) . . . . ?
C22 C17 C18 C19 0.0(4) . . . . ?
N5 C17 C18 C19 179.8(3) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
C18 C19 C20 C21 1.5(5) . . . . ?
C19 C20 C21 C22 -1.4(5) . . . . ?
C20 C21 C22 C17 0.6(4) . . . . ?
C20 C21 C22 N4 -178.7(3) . . . . ?
C18 C17 C22 C21 0.1(4) . . . . ?
N5 C17 C22 C21 -179.8(3) . . . . ?
C18 C17 C22 N4 179.6(3) . . . . ?
N5 C17 C22 N4 -0.3(3) . . . . ?
O1 C7 N1 C3 -177.8(3) . . . . ?
N2 C7 N1 C3 1.9(3) . . . . ?
C2 C3 N1 C7 178.8(3) . . . . ?
C4 C3 N1 C7 -1.0(3) . . . . ?
O1 C7 N2 C4 177.7(3) . . . . ?
N1 C7 N2 C4 -2.1(3) . . . . ?
O1 C7 N2 C8 0.6(5) . . . . ?
N1 C7 N2 C8 -179.2(2) . . . . ?
C5 C4 N2 C7 -175.3(3) . . . . ?
C3 C4 N2 C7 1.5(3) . . . . ?
C5 C4 N2 C8 1.6(5) . . . . ?
C3 C4 N2 C8 178.4(2) . . . . ?
C12 C8 N2 C7 111.8(3) . . . . ?
C9 C8 N2 C7 -122.6(3) . . . . ?
C12 C8 N2 C4 -64.8(3) . . . . ?
C9 C8 N2 C4 60.9(3) . . . . ?
C9 C10 N3 C13 173.8(2) . . . . ?
C9 C10 N3 C11 -60.7(3) . . . . ?
C14 C13 N3 C10 -153.8(2) . . . . ?
C14 C13 N3 C11 81.9(3) . . . . ?
C12 C11 N3 C10 60.4(3) . . . . ?
C12 C11 N3 C13 -173.8(2) . . . . ?
O2 C16 N4 C22 178.9(3) . . . . ?
N5 C16 N4 C22 0.1(3) . . . . ?
O2 C16 N4 C15 -5.0(4) . . . . ?
N5 C16 N4 C15 176.1(2) . . . . ?
C21 C22 N4 C16 179.5(3) . . . . ?
C17 C22 N4 C16 0.1(3) . . . . ?
C21 C22 N4 C15 3.6(5) . . . . ?
C17 C22 N4 C15 -175.8(2) . . . . ?
C14 C15 N4 C16 105.5(3) . . . . ?
C14 C15 N4 C22 -79.2(3) . . . . ?
O2 C16 N5 C17 -179.1(3) . . . . ?
N4 C16 N5 C17 -0.3(3) . . . . ?
C18 C17 N5 C16 -179.5(3) . . . . ?
C22 C17 N5 C16 0.3(3) . . . . ?
O4 C23 C24 C25 160.4(3) . . . . ?
O3 C23 C24 C25 -17.9(4) . . . . ?
O4 C23 C24 N6 -17.8(4) . . . . ?
O3 C23 C24 N6 163.9(2) . . . . ?
N6 C24 C25 C26 1.0(4) . . . . ?
C23 C24 C25 C26 -177.1(3) . . . . ?
C24 C25 C26 O5 -179.9(3) . . . . ?
C24 C25 C26 N7 -0.3(4) . . . . ?
C25 C24 N6 C27 0.0(4) . . . . ?
C23 C24 N6 C27 178.2(2) . . . . ?
O6 C27 N6 C24 179.2(3) . . . . ?
N7 C27 N6 C24 -1.7(4) . . . . ?
O6 C27 N7 C26 -178.3(3) . . . . ?
N6 C27 N7 C26 2.6(4) . . . . ?
O5 C26 N7 C27 178.0(3) . . . . ?
C25 C26 N7 C27 -1.6(4) . . . . ?
