#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:08:36 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290150 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/79/7247958.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_7247958
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, C6 H4 N O2, 2(H2 O), 0.805(O)'
_chemical_formula_sum            'C28 H33 Cl N6 O6.81'
_chemical_formula_weight         597.93
_chemical_name_common            'Domperidone nicotinate hydrate'
_chemical_name_systematic        'Domperidone nicotinate hydrate'
_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                99.812(5)
_cell_angle_beta                 98.717(5)
_cell_angle_gamma                102.962(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3734(18)
_cell_length_b                   10.207(2)
_cell_length_c                   21.402(5)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.8
_cell_measurement_theta_min      2.50
_cell_volume                     1516.2(6)
_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 0.992
_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            47136
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.613
_diffrn_reflns_theta_min         2.118
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6627
_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    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             628.9
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         9274
_refine_ls_number_restraints     271
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0585
_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)+(0.0944P)²+0.3852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.2079
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4761
_reflns_number_total             9274
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01000g2.cif
_cod_data_source_block           KB551_0m
_cod_depositor_comments
'Adding full bibliography for 7247958--7247965.cif.'
_cod_database_code               7247958
_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   0.981
_shelx_estimated_absorpt_t_max   0.984
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 1.2344(3) 1.1031(2) 0.51153(11) 0.0481(5) Uani 1 1 d . . . . .
C2 C 1.2361(3) 1.0071(2) 0.45780(10) 0.0463(4) Uani 1 1 d . . . . .
H2 H 1.219045 1.025089 0.416450 0.056 Uiso 1 1 calc R U . . .
C3 C 1.2644(2) 0.88275(19) 0.46866(9) 0.0414(4) Uani 1 1 d . . . . .
C4 C 1.2906(3) 0.85554(19) 0.53078(9) 0.0417(4) Uani 1 1 d . . . . .
C5 C 1.2864(3) 0.9521(2) 0.58357(10) 0.0501(5) Uani 1 1 d . . . . .
H5 H 1.301809 0.934067 0.624928 0.060 Uiso 1 1 calc R U . . .
C6 C 1.2583(3) 1.0781(2) 0.57314(11) 0.0522(5) Uani 1 1 d . . . . .
H6 H 1.255632 1.145536 0.607963 0.063 Uiso 1 1 calc R U . . .
C7 C 1.3016(3) 0.6675(2) 0.45853(9) 0.0431(4) Uani 1 1 d . . . . .
C8 C 1.3402(3) 0.6407(2) 0.57262(9) 0.0437(4) Uani 1 1 d . . . . .
H8 H 1.367435 0.556305 0.551365 0.052 Uiso 1 1 calc R U . . .
C9 C 1.5055(3) 0.7112(2) 0.62866(10) 0.0505(5) Uani 1 1 d . . . . .
H9A H 1.621587 0.734910 0.612258 0.061 Uiso 1 1 calc R U . . .
H9B H 1.483742 0.795473 0.651062 0.061 Uiso 1 1 calc R U . . .
C10 C 1.5267(3) 0.6173(2) 0.67517(10) 0.0502(5) Uani 1 1 d . . . . .
H10A H 1.559168 0.536728 0.653498 0.060 Uiso 1 1 calc R U . . .
H10B H 1.629840 0.664822 0.711351 0.060 Uiso 1 1 calc R U . . .
C11 C 1.1834(3) 0.5059(2) 0.64543(10) 0.0552(5) Uani 1 1 d . . . . .
H11A H 1.068527 0.484186 0.662650 0.066 Uiso 1 1 calc R U . . .
H11B H 1.201945 0.420398 0.623066 0.066 Uiso 1 1 calc R U . . .
C12 C 1.1597(3) 0.5978(2) 0.59780(10) 0.0516(5) Uani 1 1 d . . . . .
H12A H 1.056397 0.549110 0.561875 0.062 Uiso 1 1 calc R U . . .
H12B H 1.127430 0.679066 0.618867 0.062 Uiso 1 1 calc R U . . .
C13 C 1.3689(3) 0.4793(2) 0.74539(10) 0.0559(5) Uani 1 1 d . . . . .
H13A H 1.413301 0.403555 0.724749 0.067 Uiso 1 1 calc R U . . .
H13B H 1.245661 0.441264 0.754771 0.067 Uiso 1 1 calc R U . . .
C14 C 1.5062(3) 0.5520(3) 0.80820(10) 0.0624(6) Uani 1 1 d . . . . .
H14A H 1.635496 0.564884 0.801269 0.075 Uiso 1 1 calc R U . . .
H14B H 1.485671 0.641940 0.822551 0.075 Uiso 1 1 calc R U . . .
C15 C 1.4787(4) 0.4687(3) 0.85969(11) 0.0691(7) Uani 1 1 d . . . . .
H15A H 1.346851 0.449775 0.864096 0.083 Uiso 1 1 calc R U . . .
H15B H 1.508369 0.381452 0.846614 0.083 Uiso 1 1 calc R U . . .
C16 C 1.7665(4) 0.5163(3) 0.94673(12) 0.0750(8) Uani 1 1 d . . . . .
C17 C 1.7191(4) 0.6909(3) 1.01591(12) 0.0703(7) Uani 1 1 d . . . . .
C18 C 1.7299(5) 0.7979(3) 1.06661(16) 0.0922(9) Uani 1 1 d . . . . .
H18 H 1.831366 0.825840 1.101670 0.111 Uiso 1 1 calc R U . . .
C19 C 1.5843(7) 0.8608(4) 1.0628(2) 0.1192(13) Uani 1 1 d . . . . .
H19 H 1.586812 0.932636 1.096365 0.143 Uiso 1 1 calc R U . . .
C20 C 1.4338(6) 0.8210(4) 1.0108(2) 0.1179(13) Uani 1 1 d . . . . .
H20 H 1.338582 0.867397 1.009909 0.142 Uiso 1 1 calc R U . . .
C21 C 1.4216(5) 0.7140(4) 0.95994(16) 0.0905(9) Uani 1 1 d . . . . .
H21 H 1.320146 0.686531 0.924887 0.109 Uiso 1 1 calc R U . . .
C22 C 1.5672(4) 0.6499(3) 0.96380(12) 0.0682(7) Uani 1 1 d . . . . .
Cl1 Cl 1.20027(8) 1.26113(6) 0.49944(3) 0.06285(19) Uani 1 1 d . . . . .
N1 N 1.2702(2) 0.76671(17) 0.42603(9) 0.0458(4) Uani 1 1 d . . . . .
H1N H 1.273(3) 0.759(2) 0.3861(13) 0.060(7) Uiso 1 1 d . . . . .
N2 N 1.3155(2) 0.72230(16) 0.52377(7) 0.0437(4) Uani 1 1 d . . . . .
N3 N 1.3484(2) 0.57292(19) 0.69996(8) 0.0454(4) Uani 1 1 d . . . . .
H3N H 1.320(3) 0.651(3) 0.7221(12) 0.062(7) Uiso 1 1 d . . . . .
N4 N 1.5993(3) 0.5416(2) 0.92169(9) 0.0679(6) Uani 1 1 d . . . . .
N5 N 1.8388(4) 0.6076(3) 1.00390(10) 0.0765(7) Uani 1 1 d . . . . .
H5N H 1.948(5) 0.604(3) 1.0300(17) 0.105(11) Uiso 1 1 d . . . . .
O1 O 1.3119(2) 0.55205(15) 0.43550(7) 0.0538(4) Uani 1 1 d . . . . .
O2 O 1.8387(3) 0.4280(3) 0.92123(9) 0.1001(7) Uani 1 1 d . . . . .
C23 C 1.1399(9) 0.7849(6) 0.7821(3) 0.0796(16) Uani 0.776(4) 1 d . U P A 1
O3 O 1.2447(5) 0.8174(5) 0.74555(19) 0.1012(12) Uani 0.776(4) 1 d . U P A 1
O4 O 1.1400(7) 0.6839(5) 0.8091(3) 0.1240(15) Uani 0.776(4) 1 d . U P A 1
C23D C 1.157(3) 0.828(2) 0.7695(11) 0.074(3) Uani 0.224(4) 1 d D U P A 2
O4D O 1.184(2) 0.7114(13) 0.7815(5) 0.075(3) Uani 0.224(4) 1 d . U P A 2
O3D O 1.232(2) 0.8879(12) 0.7329(6) 0.096(4) Uani 0.224(4) 1 d . U P A 2
C24 C 1.0023(4) 0.8677(3) 0.79637(15) 0.0714(10) Uani 0.776(4) 1 d G U P A 1
C25 C 0.9114(4) 0.8548(3) 0.84821(14) 0.0805(10) Uani 0.776(4) 1 d G U P A 1
H25 H 0.940308 0.797130 0.875386 0.097 Uiso 0.776(4) 1 calc R U P A 1
C26 C 0.7775(5) 0.9279(3) 0.85942(15) 0.0965(12) Uani 0.776(4) 1 d G U P A 1
H26 H 0.716753 0.919228 0.894104 0.116 Uiso 0.776(4) 1 calc R U P A 1
C27 C 0.7344(4) 1.0140(3) 0.81880(17) 0.1079(14) Uani 0.776(4) 1 d G U P A 1
H27 H 0.644753 1.062985 0.826302 0.129 Uiso 0.776(4) 1 calc R U P A 1
N6 N 0.8252(4) 1.0270(3) 0.76696(15) 0.1013(11) Uani 0.776(4) 1 d G U P A 1
C28 C 0.9591(4) 0.9539(3) 0.75575(13) 0.0859(11) Uani 0.776(4) 1 d G U P A 1
H28 H 1.019864 0.962548 0.721062 0.103 Uiso 0.776(4) 1 calc R U P A 1
C24D C 1.0153(17) 0.8686(13) 0.8075(6) 0.078(2) Uani 0.224(4) 1 d DG U P A 2
C28D C 0.9996(15) 0.8440(11) 0.8686(5) 0.088(2) Uani 0.224(4) 1 d G U P A 2
H28D H 1.066972 0.787660 0.886282 0.106 Uiso 0.224(4) 1 calc R U P A 2
N6D N 0.8832(15) 0.9035(10) 0.9034(4) 0.106(2) Uani 0.224(4) 1 d G U P A 2
C27D C 0.7825(16) 0.9876(12) 0.8770(6) 0.103(2) Uani 0.224(4) 1 d G U P A 2
H27D H 0.704577 1.027450 0.900273 0.124 Uiso 0.224(4) 1 calc R U P A 2
C26D C 0.7982(16) 1.0123(12) 0.8159(6) 0.090(2) Uani 0.224(4) 1 d G U P A 2
H26D H 0.730795 1.068609 0.798284 0.108 Uiso 0.224(4) 1 calc R U P A 2
C25D C 0.9146(17) 0.9528(13) 0.7812(5) 0.088(2) Uani 0.224(4) 1 d G U P A 2
H25D H 0.925102 0.969293 0.740293 0.106 Uiso 0.224(4) 1 calc R U P A 2
O1W O 0.7275(5) 0.2376(3) 0.70617(11) 0.1305(10) Uani 1 1 d D . . . .
H1W H 0.768(7) 0.299(4) 0.7425(15) 0.196 Uiso 1 1 d D U . . .
H2W H 0.835(4) 0.222(6) 0.698(3) 0.196 Uiso 1 1 d D U . . .
O2W O 0.9416(5) 0.4431(4) 0.80281(14) 0.1511(13) Uani 1 1 d D . . . .
H3W H 0.904(8) 0.431(6) 0.8381(16) 0.227 Uiso 1 1 d D U . . .
H4W H 1.032(7) 0.517(4) 0.812(3) 0.227 Uiso 1 1 d D U . . .
O3W O 1.3863(8) 0.1417(6) 0.7494(2) 0.211(4) Uani 0.805(12) 1 d . . P B 1
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 122.60(19) . . ?
C6 C1 Cl1 119.76(17) . . ?
C2 C1 Cl1 117.65(16) . . ?
C1 C2 C3 116.58(19) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
N1 C3 C2 130.71(18) . . ?
N1 C3 C4 107.46(17) . . ?
C2 C3 C4 121.82(18) . . ?
C5 C4 C3 120.65(18) . . ?
C5 C4 N2 132.94(18) . . ?
C3 C4 N2 106.41(16) . . ?
C4 C5 C6 117.97(19) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 N1 127.36(18) . . ?
O1 C7 N2 126.17(18) . . ?
N1 C7 N2 106.45(17) . . ?
N2 C8 C12 111.39(16) . . ?
N2 C8 C9 113.66(16) . . ?
C12 C8 C9 110.11(16) . . ?
N2 C8 H8 107.1 . . ?
C12 C8 H8 107.1 . . ?
C9 C8 H8 107.1 . . ?
C10 C9 C8 110.21(17) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N3 C10 C9 111.81(16) . . ?
N3 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 C12 111.75(17) . . ?
N3 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C8 C12 C11 110.88(17) . . ?
C8 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N3 C13 C14 112.40(19) . . ?
N3 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 110.4(2) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 C14 111.3(2) . . ?
N4 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
N4 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O2 C16 N5 126.9(3) . . ?
O2 C16 N4 126.1(3) . . ?
N5 C16 N4 107.0(3) . . ?
N5 C17 C18 132.1(3) . . ?
N5 C17 C22 106.7(2) . . ?
C18 C17 C22 121.2(3) . . ?
C19 C18 C17 116.8(3) . . ?
C19 C18 H18 121.6 . . ?
C17 C18 H18 121.6 . . ?
C18 C19 C20 122.2(4) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C19 C20 C21 121.4(4) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 116.6(3) . . ?
C22 C21 H21 121.7 . . ?
C20 C21 H21 121.7 . . ?
C21 C22 C17 121.8(3) . . ?
C21 C22 N4 131.3(3) . . ?
C17 C22 N4 106.9(2) . . ?
C7 N1 C3 110.42(17) . . ?
C7 N1 H1N 121.9(17) . . ?
C3 N1 H1N 127.0(17) . . ?
C7 N2 C4 109.25(15) . . ?
C7 N2 C8 121.22(16) . . ?
C4 N2 C8 129.41(16) . . ?
C13 N3 C11 110.35(16) . . ?
C13 N3 C10 111.75(16) . . ?
C11 N3 C10 110.99(16) . . ?
C13 N3 H3N 108.3(15) . . ?
C11 N3 H3N 106.5(15) . . ?
C10 N3 H3N 108.8(15) . . ?
C16 N4 C22 109.2(2) . . ?
C16 N4 C15 124.7(2) . . ?
C22 N4 C15 126.0(2) . . ?
C16 N5 C17 110.2(2) . . ?
C16 N5 H5N 121(2) . . ?
C17 N5 H5N 129(2) . . ?
O3 C23 O4 123.7(6) . . ?
O3 C23 C24 118.8(5) . . ?
O4 C23 C24 117.5(5) . . ?
O3D C23D O4D 124.1(12) . . ?
O3D C23D C24D 127.2(16) . . ?
O4D C23D C24D 108.7(14) . . ?
C25 C24 C28 120.0 . . ?
C25 C24 C23 120.5(3) . . ?
C28 C24 C23 119.5(3) . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
N6 C27 C26 120.0 . . ?
N6 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 N6 C28 120.0 . . ?
N6 C28 C24 120.0 . . ?
N6 C28 H28 120.0 . . ?
C24 C28 H28 120.0 . . ?
C28D C24D C25D 120.0 . . ?
C28D C24D C23D 124.9(12) . . ?
C25D C24D C23D 114.5(11) . . ?
C24D C28D N6D 120.0 . . ?
C24D C28D H28D 120.0 . . ?
N6D C28D H28D 120.0 . . ?
C28D N6D C27D 120.0 . . ?
C26D C27D N6D 120.0 . . ?
C26D C27D H27D 120.0 . . ?
N6D C27D H27D 120.0 . . ?
C27D C26D C25D 120.0 . . ?
C27D C26D H26D 120.0 . . ?
C25D C26D H26D 120.0 . . ?
C26D C25D C24D 120.0 . . ?
C26D C25D H25D 120.0 . . ?
C24D C25D H25D 120.0 . . ?
H1W O1W H2W 101(2) . . ?
H3W O2W H4W 108(3) . . ?
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 1.378(3) . ?
C1 C2 1.382(3) . ?
C1 Cl1 1.742(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.380(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.376(3) . ?
C4 N2 1.399(2) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.221(2) . ?
C7 N1 1.364(3) . ?
C7 N2 1.392(2) . ?
C8 N2 1.459(2) . ?
C8 C12 1.513(3) . ?
C8 C9 1.520(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.509(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.497(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.495(3) . ?
C11 C12 1.515(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.489(3) . ?
C13 C14 1.514(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.512(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.454(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.237(3) . ?
C16 N5 1.357(4) . ?
C16 N4 1.365(3) . ?
C17 N5 1.378(4) . ?
C17 C18 1.381(4) . ?
C17 C22 1.388(4) . ?
C18 C19 1.368(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(4) . ?
C21 H21 0.9300 . ?
C22 N4 1.390(3) . ?
N1 H1N 0.85(3) . ?
N3 H3N 0.94(3) . ?
N5 H5N 0.92(4) . ?
C23 O3 1.215(7) . ?
C23 O4 1.265(7) . ?
C23 C24 1.494(6) . ?
C23D O3D 1.20(2) . ?
C23D O4D 1.31(2) . ?
C23D C24D 1.504(10) . ?
C24 C25 1.3900 . ?
C24 C28 1.3900 . ?
C25 C26 1.3900 . ?
C25 H25 0.9300 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C27 N6 1.3900 . ?
C27 H27 0.9300 . ?
N6 C28 1.3900 . ?
C28 H28 0.9300 . ?
C24D C28D 1.3900 . ?
C24D C25D 1.3900 . ?
C28D N6D 1.3900 . ?
C28D H28D 0.9300 . ?
N6D C27D 1.3900 . ?
C27D C26D 1.3900 . ?
C27D H27D 0.9300 . ?
C26D C25D 1.3900 . ?
C26D H26D 0.9300 . ?
C25D H25D 0.9300 . ?
O1W H1W 0.875(10) . ?
O1W H2W 0.879(10) . ?
O2W H3W 0.863(10) . ?
O2W H4W 0.857(10) . ?
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 O1W 0.85(3) 1.98(3) 2.825(3) 173(2) 2_766 yes
N3 H3N O3^a 0.94(3) 1.92(3) 2.831(4) 165(2) . yes
N3 H3N O4^a 0.94(3) 2.47(3) 3.172(6) 132.2(19) . yes
N3 H3N O4D^b 0.94(3) 1.85(3) 2.660(12) 144(2) . yes
N3 H3N O3D^b 0.94(3) 2.63(3) 3.496(12) 155.0(19) . yes
N5 H5N O2 0.92(4) 1.87(4) 2.790(3) 172(3) 2_967 yes
O1W H1W O2W 0.875(10) 1.86(2) 2.686(4) 156(5) . yes
O2W H3W O2 0.863(10) 1.915(14) 2.772(4) 172(6) 1_455 yes
O2W H4W O4^a 0.857(10) 1.73(3) 2.532(7) 156(7) . yes
O2W H4W O4D^b 0.857(10) 2.30(3) 3.063(13) 149(6) . 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 -0.4(3) . . . . ?
Cl1 C1 C2 C3 179.68(14) . . . . ?
C1 C2 C3 N1 178.72(19) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
N1 C3 C4 C5 -178.24(18) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
N1 C3 C4 N2 1.1(2) . . . . ?
C2 C3 C4 N2 -179.73(17) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
N2 C4 C5 C6 179.8(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
Cl1 C1 C6 C5 -179.78(16) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
N2 C8 C9 C10 -177.29(17) . . . . ?
C12 C8 C9 C10 56.9(2) . . . . ?
C8 C9 C10 N3 -57.0(2) . . . . ?
N2 C8 C12 C11 176.52(16) . . . . ?
C9 C8 C12 C11 -56.4(2) . . . . ?
N3 C11 C12 C8 55.8(2) . . . . ?
N3 C13 C14 C15 162.7(2) . . . . ?
C13 C14 C15 N4 -175.7(2) . . . . ?
N5 C17 C18 C19 179.3(4) . . . . ?
C22 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C20 -0.6(6) . . . . ?
C18 C19 C20 C21 0.8(7) . . . . ?
C19 C20 C21 C22 -0.3(6) . . . . ?
C20 C21 C22 C17 -0.3(5) . . . . ?
C20 C21 C22 N4 -179.4(3) . . . . ?
N5 C17 C22 C21 -179.0(3) . . . . ?
C18 C17 C22 C21 0.5(4) . . . . ?
N5 C17 C22 N4 0.3(3) . . . . ?
C18 C17 C22 N4 179.8(3) . . . . ?
O1 C7 N1 C3 178.83(19) . . . . ?
N2 C7 N1 C3 0.2(2) . . . . ?
C2 C3 N1 C7 -179.85(19) . . . . ?
C4 C3 N1 C7 -0.8(2) . . . . ?
O1 C7 N2 C4 -178.13(19) . . . . ?
N1 C7 N2 C4 0.6(2) . . . . ?
O1 C7 N2 C8 -1.7(3) . . . . ?
N1 C7 N2 C8 177.01(16) . . . . ?
C5 C4 N2 C7 178.2(2) . . . . ?
C3 C4 N2 C7 -1.1(2) . . . . ?
C5 C4 N2 C8 2.1(3) . . . . ?
C3 C4 N2 C8 -177.12(18) . . . . ?
C12 C8 N2 C7 -106.5(2) . . . . ?
C9 C8 N2 C7 128.44(19) . . . . ?
C12 C8 N2 C4 69.2(2) . . . . ?
C9 C8 N2 C4 -55.9(3) . . . . ?
C14 C13 N3 C11 -167.99(19) . . . . ?
C14 C13 N3 C10 68.0(2) . . . . ?
C12 C11 N3 C13 -179.35(18) . . . . ?
C12 C11 N3 C10 -54.9(2) . . . . ?
C9 C10 N3 C13 179.49(17) . . . . ?
C9 C10 N3 C11 55.8(2) . . . . ?
O2 C16 N4 C22 -179.0(3) . . . . ?
N5 C16 N4 C22 0.0(3) . . . . ?
O2 C16 N4 C15 -0.8(5) . . . . ?
N5 C16 N4 C15 178.2(2) . . . . ?
C21 C22 N4 C16 179.1(3) . . . . ?
C17 C22 N4 C16 -0.2(3) . . . . ?
C21 C22 N4 C15 0.9(5) . . . . ?
C17 C22 N4 C15 -178.4(2) . . . . ?
C14 C15 N4 C16 -100.7(3) . . . . ?
C14 C15 N4 C22 77.2(3) . . . . ?
O2 C16 N5 C17 179.2(3) . . . . ?
N4 C16 N5 C17 0.2(3) . . . . ?
C18 C17 N5 C16 -179.8(3) . . . . ?
C22 C17 N5 C16 -0.4(3) . . . . ?
O3 C23 C24 C25 -165.3(4) . . . . ?
O4 C23 C24 C25 14.8(7) . . . . ?
O3 C23 C24 C28 17.5(7) . . . . ?
O4 C23 C24 C28 -162.4(4) . . . . ?
C28 C24 C25 C26 0.0 . . . . ?
C23 C24 C25 C26 -177.2(4) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 N6 0.0 . . . . ?
C26 C27 N6 C28 0.0 . . . . ?
C27 N6 C28 C24 0.0 . . . . ?
C25 C24 C28 N6 0.0 . . . . ?
C23 C24 C28 N6 177.3(4) . . . . ?
O3D C23D C24D C28D -147(2) . . . . ?
O4D C23D C24D C28D 34(2) . . . . ?
O3D C23D C24D C25D 24(3) . . . . ?
O4D C23D C24D C25D -154.6(15) . . . . ?
C25D C24D C28D N6D 0.0 . . . . ?
C23D C24D C28D N6D 170.6(16) . . . . ?
C24D C28D N6D C27D 0.0 . . . . ?
C28D N6D C27D C26D 0.0 . . . . ?
N6D C27D C26D C25D 0.0 . . . . ?
C27D C26D C25D C24D 0.0 . . . . ?
C28D C24D C25D C26D 0.0 . . . . ?
C23D C24D C25D C26D -171.5(15) . . . . ?
