2-Amino-5-chloro­pyridin-1-ium barbiturate dihydrate

Anantheeswary, T.R.; Gomathi, S.; Nirmalram, J.S.; Perdih, F.

doi:10.1107/S2414314626003512

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 4| April 2026| x260351

https://doi.org/10.1107/S2414314626003512

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2-Amino-5-chloropyridin-1-ium barbiturate dihydrate

Thankappan Ramalakshmi Anantheeswary,^a Sundaramoorthy Gomathi,^a ^* Jeyaraman Selvaraj Nirmalram ^b and Franc Perdih ^c

^aDepartment of Chemistry, Periyar Maniammai Institute of Science & Technology, Thanjavur, Tamilnadu-613403, India, ^bDepartment of Chemistry, Government Arts and Science College, Karambakudi, Pudukottai, Tamilnadu-622302, India, and ^cFaculty of Chemistry and Chemical Technology, University of Ljubljana, Slovenia
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 9 March 2026; accepted 6 April 2026; online 10 April 2026)

In the title hydrated salt, C₅H₆ClN₂⁺·C₄H₃N₂O₃⁻·2H₂O, the asymmetric unit contains two cations, two anions and four water molecules of crystallization. In the extended structure, the barbiturate (2,4,6-trioxo-1,3-diazinan-5-ide) anions form a wave-like supramolecular [001] chain decorated by the cations, mediated by numerous N—H⋯O hydrogen bonds. Adjacent chains are cross-linked by [010] chains of water molecules featuring four- and six-membered rings and five-membered carboxylate aggregates via O—H⋯O hydrogen bonds.

Keywords: crystal structure; molecular salt; 2-amino-5-chloropyridinium cation; barbiturate anion.

CCDC reference: 2543974

Structure description

The crystal structure of 2-amino-5-chloropyridine, C₅H₅ClN₂ (Kvick & Backéus, 1974 ) and its diverse salts with dicarboxylic acids (Jayanalina et al., 2015 ), aromatic acids (Hanif et al., 2020 ) and other inorganic anions such as nitrate (Zaouali Zgolli et al., 2009 ), phosphate (Akriche & Rzaigui, 2005 ), sulfonate (Jagan & Boopathi, 2020 ) and trifluoroacetate (Hemamalini & Fun, 2010 ) have been extensively studied, highlighting its diverse hydrogen-bonding interactions. Barbiturates derived from barbituric acid (C₄H₄N₂O₃) play a significant role in biological systems (Hueso Ureña et al., 2003 ). Research on barbiturate salts and co-crystals demonstrate that hydrogen bonding is a key driving force for structure and property modulation.

Hydrogen bonding not only increases the reactivity and electrophilicity of barbiturates (Bauer & Spange, 2010 ), but also governs their supramolecular organization in host–guest systems and polymeric assemblies, particularly those involving Hamilton-type receptors (Chang & Hamilton, 1988 ). Thus hydrogen bonding acts as the primary driving force behind barbiturate self-assembly and functional behaviour and indicates its significance in supramolecular chemistry, materials science and biomimetic design. As part of our studies in this area, we now report the synthesis and structure of the title hydrated salt, C₅H₆ClN₂⁺·C₄H₃N₂O₃⁻·2H₂O (I).

The asymmetric unit of (I) consists of two crystallographically independent 2-amino-5-chloropyridinium cations, two barbiturate anions and four water molecules of crystallization in space group P2₁/c. The proton acceptance from the barbituric acid occurs at the pyridine ring N atoms of the cations (Fig. 1) which is evident from the widening of the C1—N1—C5 and C6—N3—C10 bond angles [122.67 (13) and 122.84 (14)°, respectively] compared to the unprotonated molecule, in which the bond angle is around 118° (Anantheeswary et al., 2024 ). The deprotonation of the barbituric acid occurs from the active methylene groups (atoms C13 and C17) driven by the electron withdrawing carbonyl group at both sides and this is supported by the sp² hybridization at these atoms in (I) implied by the C—C—C bond angles [C12—C13—C14 = 121.55 (14); C16—C17—C18 = 121.61 (14)°]. Overall, both barbiturate anions display a nearly planar six-membered ring: the deviations of the atoms from the mean plane are small (±0.025 Å and ±0.013 Å for the O1 and O4 anions, respectively). These structural parameters align well with known data for barbiturate systems (Gelbrich et al., 2015 ) and indicate that the barbiturate anion in (I) adopts a stabilized, delocalized and nearly planar conformation.

Figure 1
The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

In the extended structure of (I), the anions are linked by pairwise N—H⋯O hydrogen bonds into wave-like [001] ribbons, with the O1 and O4 anions alternating in the chains. Atoms N5 and N7 (donors) and carbonyl oxygen atoms O3 and O6 (acceptors) form one pairwise linkage and atoms N6 and N8 (donors) and O1 and O4 (acceptors) the other, which leads to two distinct R₂²(8) ring motifs (Table 1). The [001] chains are decorated by the cations: the C1 cation links to atoms O1, O5 and O6 in the anions and the C6 cation to O2, O3 and O4 via strong N—H⋯O hydrogen bonds to render R₃²(10) ring motifs. Taken together, these hydrogen bonds lead to propagate a wave-like supramolecular ribbon as shown in Fig. 2. Adjacent anion/cation supramolecular sheets are connected by four- and six-membered [010] tape-like arrays of water molecules which form various O_w—H_w⋯O_w and O_w—H_w⋯O_c (w = water, c = carbonyl) hydrogen bonds. This arrangement has a close resemblance to the water tape T4(2) and T6(2) motifs in the systematic classification of hydrated organic crystal structures reported in the literature (Infantes & Motherwell, 2002 ). In addition, the interaction between the water molecules O7, O9 and O10 and the carbonyl O2 atom of the anion leads to an R₅⁴(10) ring motif. The existence of the four- and six-membered water loops and five-membered carbonyl–water loops generates two different DDAA (D = donor, A = acceptor) hydrogen-bonded arrays with ring motifs of R₅⁴(10), R₆⁶(12) and R₅⁴(10) and R₅⁴(10), R₄²(8) and R₅⁴(10), along the a axis direction as shown in Fig. 3.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.87	1.85	2.7207 (18)	176
N2—H2A⋯O1	0.89	2.02	2.7461 (18)	138
N2—H2B⋯O5ⁱ	0.89	1.87	2.7610 (17)	180
N3—H3A⋯O3	0.86	1.83	2.6863 (18)	177
N4—H4A⋯O4	0.87	2.00	2.7248 (18)	139
N4—H4B⋯O2ⁱⁱ	0.89	1.97	2.8606 (17)	173
N5—H5A⋯O6	0.87	2.02	2.8786 (17)	173
N6—H6⋯O4ⁱ	0.89	2.03	2.9005 (17)	170
N7—H7A⋯O3	0.87	2.06	2.8985 (17)	163
N8—H8A⋯O1ⁱⁱ	0.88	2.01	2.8762 (16)	172
O7—H7B⋯O5	0.86	1.92	2.7581 (16)	164
O7—H7C⋯O2ⁱⁱⁱ	0.82	2.13	2.9155 (18)	160
O8—H8B⋯O10	0.86	1.89	2.739 (2)	167
O8—H8C⋯O2	0.89	1.91	2.7810 (16)	165
O9—H9A⋯O8	0.86	1.93	2.7864 (18)	168
O10—H10B⋯O7ⁱⁱⁱ	0.87	1.96	2.8287 (18)	175
C10—H10⋯O7ⁱⁱⁱ	0.95	2.44	3.321 (2)	153
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
A view of a wave-like supramolecular chain built up from N—H⋯O hydrogen bonds [symmetry codes: (i) x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z; (ii) x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z].

Figure 3
A water chain extending along the c-axis direction cross-linking the supramolecular chains [symmetry code: (iii) 1 − x, $[{1\over 2}]$ + y, 3/2 - −z].

A possible offset aromatic π–π stacking interaction between barbiturate rings [Cg1⋯Cg2^vi; symmetry code: (vi) 1 − x, − $[{1\over 2}]$ + y, 3/2 − z; Cg1 = C11–C14/N5/N6 centroid; Cg2 = C15–C18/N7/N8 centroid] occurs with centroid-to-centroid and perpendicular distances of 3.7978 (9) and 3.4530 (6) Å, respectively. However, the large slippage angle of 30.5° suggests that this interaction is weak.

Synthesis and crystallization

The title compound was synthesized by mixing 20 ml ethanol:water (1:1 v/v) solutions of 2-amino-5-chloropyridine (0.25 mmol) and barbituric acid (0.25 mmol) and the resulting clear solution was then warmed over a water bath for 20 min at 353 K. The solution was then allowed to cool to room temperature and after a few days, colourless crystals of (I) were separated out from the mother liquor.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₅H₆ClN₂⁺·C₄H₃N₂O₃⁻·2H₂O
M_r	292.68
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	18.8228 (10), 6.9495 (4), 19.3563 (10)
β (°)	99.817 (5)
V (Å³)	2494.9 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.33
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	SuperNova, Dual, Cu at home/near, Atlas
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 )
T_min, T_max	0.812, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13946, 6542, 5147
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.712

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.108, 1.04
No. of reflections	6542
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.30
Computer programs: CrysAlis PRO (Rigaku OD, 2019), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), PLATON (Spek, 2020 ), Mercury (Macrae et al., 2020 ), POVRay (Cason, 2004 ), PLATON (Spek, 2020) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2543974

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314626003512/hb4559sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626003512/hb4559Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626003512/hb4559Isup3.cml

checkCIF report

Computing details top

2-Amino-5-chloropyridin-1-ium 2,4,6-trioxo-1,3-diazinan-5-ide dihydrate top

Crystal data top

C₅H₆ClN₂⁺·C₄H₃N₂O₃⁻·2H₂O	F(000) = 1216
M_r = 292.68	D_x = 1.558 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4971 reflections
a = 18.8228 (10) Å	θ = 3.6–30.0°
b = 6.9495 (4) Å	µ = 0.33 mm⁻¹
c = 19.3563 (10) Å	T = 150 K
β = 99.817 (5)°	Prism, yellow
V = 2494.9 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 8

Data collection top

SuperNova, Dual, Cu at home/near, Atlas diffractometer	6542 independent reflections
Radiation source: micro-focus sealed X-ray tube	5147 reflections with I > 2σ(I)
SuperNova (Mo) X-ray Source monochromator	R_int = 0.023
Detector resolution: 10.4933 pixels mm^-1	θ_max = 30.4°, θ_min = 2.6°
ωw scans	h = −24→24
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	k = −9→6
T_min = 0.812, T_max = 1.000	l = −18→25
13946 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.108	W = 1/[Σ²(FO²) + (0.0476P)² + 0.6984P] WHERE P = (FO² + 2FC²)/3
S = 1.04	(Δ/σ)_max = 0.001
6542 reflections	Δρ_max = 0.33 e Å⁻³
343 parameters	Δρ_min = −0.30 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

The H atoms of the –NH₂ groups were located from a difference Fourier map and refined freely. The other H atoms were placed geometrically and refined using a riding model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.87257 (2)	0.58875 (6)	0.79957 (2)	0.0262 (1)
Cl2	0.01456 (2)	0.65022 (7)	0.64189 (2)	0.0331 (1)
O1	0.48161 (6)	0.29532 (19)	0.55832 (5)	0.0241 (3)
O2	0.24377 (6)	0.15226 (18)	0.50080 (5)	0.0232 (3)
O3	0.33892 (6)	0.45699 (17)	0.71542 (5)	0.0209 (3)
N5	0.40902 (7)	0.3677 (2)	0.63664 (6)	0.0172 (3)
N6	0.36206 (6)	0.2313 (2)	0.52973 (6)	0.0180 (3)
O4	0.39978 (6)	0.39067 (19)	0.89731 (6)	0.0272 (4)
O5	0.63610 (6)	0.23191 (18)	0.95562 (5)	0.0229 (3)
O6	0.53956 (6)	0.46773 (18)	0.73026 (5)	0.0216 (3)
C11	0.42087 (8)	0.2982 (2)	0.57385 (7)	0.0178 (4)
C12	0.29255 (8)	0.2292 (2)	0.54502 (7)	0.0178 (4)
C13	0.28334 (8)	0.3118 (2)	0.60855 (7)	0.0190 (4)
C14	0.34145 (8)	0.3827 (2)	0.65576 (7)	0.0173 (4)
N7	0.47177 (7)	0.4344 (2)	0.81589 (6)	0.0189 (4)
N8	0.51837 (7)	0.3158 (2)	0.92568 (6)	0.0199 (4)
C15	0.46008 (8)	0.3809 (2)	0.88069 (8)	0.0192 (4)
C16	0.58734 (8)	0.2981 (2)	0.90937 (8)	0.0178 (4)
C17	0.59555 (8)	0.3545 (2)	0.84172 (7)	0.0190 (4)
C18	0.53785 (8)	0.4195 (2)	0.79346 (7)	0.0177 (4)
N1	0.67547 (7)	0.4856 (2)	0.70029 (6)	0.0192 (4)
N2	0.62458 (7)	0.3966 (2)	0.58823 (7)	0.0261 (4)
C1	0.68229 (8)	0.4424 (2)	0.63372 (8)	0.0196 (4)
C2	0.75242 (8)	0.4493 (2)	0.61612 (8)	0.0217 (5)
C3	0.81029 (8)	0.4945 (2)	0.66553 (8)	0.0220 (4)
C4	0.79994 (8)	0.5347 (2)	0.73472 (8)	0.0199 (4)
C5	0.73289 (8)	0.5300 (2)	0.75058 (8)	0.0199 (4)
N3	0.20843 (7)	0.53881 (19)	0.74635 (6)	0.0188 (4)
N4	0.25572 (7)	0.4593 (2)	0.86099 (7)	0.0244 (4)
C6	0.19906 (8)	0.5027 (2)	0.81288 (8)	0.0193 (4)
O7	0.77655 (6)	0.2806 (2)	0.93547 (6)	0.0325 (4)
C7	0.12861 (9)	0.5152 (3)	0.82787 (8)	0.0253 (5)
C8	0.07259 (9)	0.5605 (3)	0.77660 (8)	0.0265 (5)
C9	0.08531 (9)	0.5963 (2)	0.70812 (8)	0.0224 (5)
C10	0.15318 (9)	0.5862 (2)	0.69438 (8)	0.0217 (4)
O8	0.09636 (6)	0.2133 (2)	0.49087 (6)	0.0346 (4)
O9	−0.00582 (7)	0.1255 (2)	0.57464 (7)	0.0385 (4)
O10	0.11145 (7)	0.6003 (2)	0.47080 (7)	0.0395 (4)
H5A	0.44601	0.40394	0.66680	0.0210*
H6	0.36970	0.18200	0.48947	0.0220*
H13	0.23625	0.31983	0.61984	0.0230*
H7A	0.43332	0.46700	0.78672	0.0230*
H8A	0.51061	0.27394	0.96639	0.0240*
H17	0.64191	0.34797	0.82868	0.0230*
H1	0.63257	0.47895	0.71181	0.0230*
H2	0.75892	0.42205	0.56951	0.0260*
H2A	0.58118	0.38803	0.60077	0.0310*
H2B	0.62828	0.35503	0.54527	0.0310*
H3	0.85722	0.49913	0.65372	0.0260*
H5	0.72573	0.55782	0.79696	0.0240*
H3A	0.25032	0.51691	0.73631	0.0230*
H4A	0.29875	0.44901	0.85025	0.0290*
H4B	0.24985	0.43301	0.90465	0.0290*
H7	0.12025	0.49171	0.87417	0.0300*
H8	0.02506	0.56796	0.78680	0.0320*
H10	0.16226	0.61216	0.64850	0.0260*
H7B	0.73332	0.24406	0.93811	0.0490*
H7C	0.77982	0.39306	0.94911	0.0490*
H8B	0.09589	0.33708	0.48869	0.0520*
H8C	0.14319	0.18508	0.50149	0.0520*
H9A	0.03030	0.14603	0.55342	0.0580*
H9B	−0.02290	0.01903	0.55642	0.0580*
H10A	0.07720	0.68196	0.45889	0.0590*
H10B	0.14490	0.65296	0.50189	0.0590*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0180 (2)	0.0300 (2)	0.0287 (2)	−0.0023 (2)	−0.0017 (1)	−0.0038 (2)
Cl2	0.0236 (2)	0.0411 (3)	0.0310 (2)	0.0059 (2)	−0.0059 (2)	0.0034 (2)
O1	0.0148 (5)	0.0390 (7)	0.0196 (5)	−0.0032 (5)	0.0062 (4)	−0.0073 (5)
O2	0.0161 (5)	0.0331 (7)	0.0197 (5)	−0.0034 (5)	0.0015 (4)	−0.0030 (5)
O3	0.0169 (5)	0.0315 (7)	0.0152 (5)	0.0011 (5)	0.0052 (4)	−0.0026 (5)
N5	0.0130 (6)	0.0243 (7)	0.0144 (5)	−0.0011 (5)	0.0026 (4)	−0.0022 (5)
N6	0.0146 (6)	0.0263 (7)	0.0136 (5)	−0.0008 (5)	0.0040 (4)	−0.0027 (5)
O4	0.0157 (5)	0.0467 (8)	0.0205 (5)	0.0053 (5)	0.0072 (4)	0.0080 (5)
O5	0.0160 (5)	0.0336 (7)	0.0186 (5)	0.0033 (5)	0.0018 (4)	0.0047 (5)
O6	0.0168 (5)	0.0346 (7)	0.0138 (5)	0.0001 (5)	0.0042 (4)	0.0025 (5)
C11	0.0160 (7)	0.0216 (8)	0.0163 (7)	0.0001 (6)	0.0038 (5)	−0.0005 (6)
C12	0.0151 (7)	0.0221 (8)	0.0166 (7)	0.0003 (6)	0.0035 (5)	0.0039 (6)
C13	0.0139 (7)	0.0253 (9)	0.0184 (7)	0.0010 (6)	0.0048 (5)	0.0017 (6)
C14	0.0173 (7)	0.0211 (8)	0.0145 (6)	0.0016 (6)	0.0057 (5)	0.0030 (6)
N7	0.0149 (6)	0.0278 (8)	0.0141 (6)	0.0025 (5)	0.0028 (4)	0.0031 (5)
N8	0.0165 (6)	0.0299 (8)	0.0139 (6)	0.0022 (6)	0.0047 (5)	0.0056 (6)
C15	0.0156 (7)	0.0250 (8)	0.0177 (7)	0.0004 (6)	0.0050 (5)	0.0013 (6)
C16	0.0149 (7)	0.0200 (8)	0.0190 (7)	0.0005 (6)	0.0044 (5)	0.0002 (6)
C17	0.0140 (7)	0.0250 (8)	0.0187 (7)	0.0000 (6)	0.0052 (5)	0.0007 (6)
C18	0.0162 (7)	0.0207 (8)	0.0170 (7)	−0.0028 (6)	0.0055 (5)	−0.0030 (6)
N1	0.0150 (6)	0.0256 (7)	0.0180 (6)	−0.0013 (5)	0.0059 (5)	−0.0010 (6)
N2	0.0182 (7)	0.0417 (9)	0.0190 (6)	−0.0050 (6)	0.0047 (5)	−0.0073 (6)
C1	0.0186 (7)	0.0216 (8)	0.0190 (7)	−0.0008 (6)	0.0045 (6)	0.0000 (6)
C2	0.0211 (8)	0.0256 (9)	0.0202 (7)	−0.0011 (6)	0.0091 (6)	−0.0025 (7)
C3	0.0165 (7)	0.0230 (8)	0.0283 (8)	−0.0016 (6)	0.0090 (6)	−0.0021 (7)
C4	0.0172 (7)	0.0187 (8)	0.0228 (7)	−0.0017 (6)	0.0010 (6)	−0.0005 (6)
C5	0.0204 (8)	0.0221 (8)	0.0172 (7)	−0.0002 (6)	0.0030 (5)	−0.0018 (6)
N3	0.0155 (6)	0.0226 (7)	0.0193 (6)	0.0012 (5)	0.0061 (5)	0.0011 (5)
N4	0.0171 (7)	0.0359 (9)	0.0206 (6)	0.0036 (6)	0.0040 (5)	0.0044 (6)
C6	0.0181 (7)	0.0214 (8)	0.0189 (7)	0.0005 (6)	0.0046 (5)	−0.0012 (6)
O7	0.0206 (6)	0.0332 (7)	0.0451 (7)	−0.0004 (5)	0.0095 (5)	−0.0077 (6)
C7	0.0195 (8)	0.0368 (10)	0.0211 (7)	0.0022 (7)	0.0080 (6)	0.0024 (7)
C8	0.0168 (8)	0.0342 (10)	0.0295 (8)	0.0017 (7)	0.0070 (6)	0.0007 (8)
C9	0.0189 (8)	0.0225 (8)	0.0245 (8)	0.0024 (6)	0.0000 (6)	0.0009 (7)
C10	0.0240 (8)	0.0225 (8)	0.0187 (7)	0.0006 (6)	0.0040 (6)	0.0021 (6)
O8	0.0204 (6)	0.0406 (8)	0.0424 (7)	0.0008 (6)	0.0046 (5)	0.0027 (6)
O9	0.0387 (8)	0.0413 (8)	0.0380 (7)	0.0019 (6)	0.0135 (6)	0.0028 (6)
O10	0.0297 (7)	0.0445 (9)	0.0434 (7)	0.0032 (6)	0.0039 (6)	−0.0042 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7322 (16)	C1—C2	1.419 (2)
Cl2—C9	1.7249 (17)	N2—H2A	0.8900
O1—C11	1.2309 (19)	C2—C3	1.358 (2)
O2—C12	1.2624 (18)	N2—H2B	0.8900
O3—C14	1.2732 (17)	C3—C4	1.414 (2)
N5—C11	1.3611 (18)	C4—C5	1.349 (2)
N5—C14	1.388 (2)	C2—H2	0.9500
N6—C11	1.3596 (19)	C3—H3	0.9500
N6—C12	1.3899 (19)	N3—C10	1.358 (2)
O4—C15	1.2332 (19)	N3—C6	1.3527 (19)
N5—H5A	0.8700	N4—C6	1.326 (2)
O5—C16	1.2551 (19)	C5—H5	0.9500
O6—C18	1.2741 (17)	N3—H3A	0.8600
N6—H6	0.8900	N4—H4B	0.8900
C12—C13	1.3944 (19)	N4—H4A	0.8700
C13—C14	1.391 (2)	C6—C7	1.408 (2)
N7—C15	1.3616 (19)	C7—C8	1.356 (2)
N7—C18	1.389 (2)	C8—C9	1.409 (2)
N8—C15	1.357 (2)	C9—C10	1.350 (2)
N8—C16	1.393 (2)	C7—H7	0.9500
C13—H13	0.9500	O7—H7C	0.8200
N7—H7A	0.8700	O7—H7B	0.8600
N8—H8A	0.8800	C8—H8	0.9500
C16—C17	1.400 (2)	C10—H10	0.9500
C17—C18	1.382 (2)	O8—H8B	0.8600
N1—C1	1.3503 (19)	O8—H8C	0.8900
N1—C5	1.361 (2)	O9—H9A	0.8600
N2—C1	1.316 (2)	O9—H9B	0.8600
C17—H17	0.9500	O10—H10A	0.8600
N1—H1	0.8700	O10—H10B	0.8700

C11—N5—C14	124.19 (13)	C1—N1—H1	118.00
C11—N6—C12	124.41 (12)	C1—N2—H2A	122.00
C11—N5—H5A	118.00	C1—N2—H2B	121.00
C14—N5—H5A	118.00	C1—C2—C3	120.39 (14)
C11—N6—H6	117.00	H2A—N2—H2B	117.00
C12—N6—H6	119.00	C2—C3—C4	119.29 (14)
O1—C11—N6	122.12 (13)	C3—C4—C5	119.74 (14)
N5—C11—N6	116.26 (13)	Cl1—C4—C3	120.67 (12)
O1—C11—N5	121.62 (13)	Cl1—C4—C5	119.58 (12)
O2—C12—N6	117.54 (12)	N1—C5—C4	120.16 (14)
O2—C12—C13	125.94 (14)	C1—C2—H2	120.00
N6—C12—C13	116.52 (13)	C3—C2—H2	120.00
C12—C13—C14	121.55 (14)	C2—C3—H3	120.00
O3—C14—C13	126.36 (14)	C4—C3—H3	120.00
N5—C14—C13	116.88 (12)	C6—N3—C10	122.84 (14)
O3—C14—N5	116.75 (13)	N1—C5—H5	120.00
C15—N7—C18	124.15 (13)	C4—C5—H5	120.00
C15—N8—C16	124.54 (12)	C10—N3—H3A	120.00
C14—C13—H13	119.00	C6—N3—H3A	117.00
C12—C13—H13	119.00	C6—N4—H4A	121.00
C15—N7—H7A	115.00	H4A—N4—H4B	119.00
C18—N7—H7A	120.00	C6—N4—H4B	120.00
C15—N8—H8A	117.00	N3—C6—C7	117.72 (14)
C16—N8—H8A	119.00	N3—C6—N4	119.42 (14)
O4—C15—N8	122.03 (14)	N4—C6—C7	122.86 (14)
N7—C15—N8	116.25 (13)	C6—C7—C8	120.38 (15)
O4—C15—N7	121.72 (14)	C7—C8—C9	119.60 (16)
O5—C16—N8	117.85 (13)	C8—C9—C10	119.63 (15)
O5—C16—C17	125.85 (14)	Cl2—C9—C8	120.28 (13)
N8—C16—C17	116.29 (13)	Cl2—C9—C10	120.09 (12)
C16—C17—C18	121.61 (14)	N3—C10—C9	119.82 (14)
O6—C18—C17	126.11 (14)	C6—C7—H7	120.00
N7—C18—C17	117.09 (12)	C8—C7—H7	120.00
O6—C18—N7	116.80 (13)	H7B—O7—H7C	106.00
C1—N1—C5	122.67 (13)	C7—C8—H8	120.00
C16—C17—H17	119.00	C9—C8—H8	120.00
C18—C17—H17	119.00	N3—C10—H10	120.00
N1—C1—N2	119.38 (14)	C9—C10—H10	120.00
N1—C1—C2	117.72 (14)	H8B—O8—H8C	103.00
N2—C1—C2	122.90 (14)	H9A—O9—H9B	103.00
C5—N1—H1	119.00	H10A—O10—H10B	109.00

C14—N5—C11—O1	176.94 (14)	C16—C17—C18—O6	−177.54 (14)
C14—N5—C11—N6	−3.5 (2)	C16—C17—C18—N7	2.7 (2)
C11—N5—C14—O3	−177.60 (13)	C5—N1—C1—N2	178.47 (14)
C11—N5—C14—C13	3.6 (2)	C5—N1—C1—C2	−1.7 (2)
C12—N6—C11—O1	179.22 (14)	C1—N1—C5—C4	0.9 (2)
C12—N6—C11—N5	−0.4 (2)	N1—C1—C2—C3	1.2 (2)
C11—N6—C12—O2	−175.86 (14)	N2—C1—C2—C3	−178.93 (14)
C11—N6—C12—C13	3.7 (2)	C1—C2—C3—C4	0.0 (2)
O2—C12—C13—C14	176.03 (14)	C2—C3—C4—Cl1	178.85 (11)
N6—C12—C13—C14	−3.5 (2)	C2—C3—C4—C5	−0.8 (2)
C12—C13—C14—O3	−178.55 (14)	Cl1—C4—C5—N1	−179.26 (11)
C12—C13—C14—N5	0.1 (2)	C3—C4—C5—N1	0.4 (2)
C18—N7—C15—O4	−177.42 (14)	C10—N3—C6—N4	−179.28 (14)
C18—N7—C15—N8	2.4 (2)	C10—N3—C6—C7	0.1 (2)
C15—N7—C18—O6	177.04 (14)	C6—N3—C10—C9	−0.9 (2)
C15—N7—C18—C17	−3.2 (2)	N3—C6—C7—C8	0.5 (3)
C16—N8—C15—O4	178.69 (14)	N4—C6—C7—C8	179.89 (17)
C16—N8—C15—N7	−1.1 (2)	C6—C7—C8—C9	−0.4 (3)
C15—N8—C16—O5	−178.53 (14)	C7—C8—C9—Cl2	178.93 (15)
C15—N8—C16—C17	0.7 (2)	C7—C8—C9—C10	−0.4 (3)
O5—C16—C17—C18	177.64 (14)	Cl2—C9—C10—N3	−178.31 (11)
N8—C16—C17—C18	−1.6 (2)	C8—C9—C10—N3	1.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.87	1.85	2.7207 (18)	176
N2—H2A···O1	0.89	2.02	2.7461 (18)	138
N2—H2B···O5ⁱ	0.89	1.87	2.7610 (17)	180
N3—H3A···O3	0.86	1.83	2.6863 (18)	177
N4—H4A···O4	0.87	2.00	2.7248 (18)	139
N4—H4B···O2ⁱⁱ	0.89	1.97	2.8606 (17)	173
N5—H5A···O6	0.87	2.02	2.8786 (17)	173
N6—H6···O4ⁱ	0.89	2.03	2.9005 (17)	170
N7—H7A···O3	0.87	2.06	2.8985 (17)	163
N8—H8A···O1ⁱⁱ	0.88	2.01	2.8762 (16)	172
O7—H7B···O5	0.86	1.92	2.7581 (16)	164
O7—H7C···O2ⁱⁱⁱ	0.82	2.13	2.9155 (18)	160
O8—H8B···O10	0.86	1.89	2.739 (2)	167
O8—H8C···O2	0.89	1.91	2.7810 (16)	165
O9—H9A···O8	0.86	1.93	2.7864 (18)	168
O10—H10B···O7ⁱⁱⁱ	0.87	1.96	2.8287 (18)	175
C10—H10···O7ⁱⁱⁱ	0.95	2.44	3.321 (2)	153

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2.

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