Hydrogen-bonded supra­molecular motifs in 2-amino-4,6-dimethoxy­pyrimidinium picrate and pyrimeth­aminium picrate dimethyl sulfoxide solvate

In the crystal structures of 2-amino-4,6-dimethoxy­pyri­mi­din­ium 2,4,6-trinitro­phenolate (picrate), C₆H₁₀N₃O₂⁺·C₆H₂N₃O₇⁻, (I), and 2,4-diamino-5-(4-chloro­phen­yl)-6-ethyl­pyri­midin-1-ium (pyrimethaminium or PMN) picrate dimethyl sulfoxide solvate, C₁₂H₁₄ClN₄⁺·C₆H₂N₃O₇⁻·C₂H₆OS, (II), the 2-amino-4,6-dimethoxy­pyrimidine and PMN cations are protonated at one of the pyrimidine N atoms. The picrate anion inter­acts with the protonated cations through bifurcated N—H...O hydrogen bonds, forming R₂¹(6) and R₁²(6) ring motifs. In (I), Z′ = 2. In (II), two inversion-related PMN cations are connected through a pair of N—H...N hydrogen bonds involving the 4-amino group and the uncharged N atom of the pyrimidine ring, forming a cyclic hydrogen-bonded R₂²(8) motif. In addition to the pairing, the O atom of the dimethyl sulfoxide solvent mol­ecule bridges the 2-amino and 4-amino groups on both sides of the paired bases, resulting in a self-complementary …DADA… array of quadruple hydro­gen-bonding patterns.

S1. Comment

Picric acid functions not only as an acceptor to form π-stacking complexes with aromatic biomolecules but also as an acidic ligand to form salts with polar biomolecules through specific electrostatic or hydrogen-bonding interactions (In et al., 1997). Picric acid forms charge-transfer complexes with organic compounds. Crystalline picrates have commonly been used in the preparation of amine derivatives in qualitative organic chemistry (Shriner et al., 1980). Dimethyl sulfoxide (DMSO) is a versatile solvent, which can dissolve various organic substances, and can form crystalline solvates in which it is either disordered (Deetz et al., 2000; Harper et al., 2001) or well ordered (TranQui et al., 1998). Hydrogen bonding plays a key role in molecular recognition and crystal engineering research (Desiraju, 1989). Some derivatives of pyrimidines are used as antiviral, antitumor and cardiovascular agents (Atwal et al., 1989). Pyrimethamine is a well known antifolate drug used in the treatment of malaria. In the chemotheraphy of malaria and neoplastic diseases, substituted 2,4-diaminopyrimidines are widely employed as metabolic inhibitors of pathways leading to the synthesis of proteins and nucleic acid (Hitchings & Burchall, 1965). Pyrimethamine is also used along with other drugs for the treatment of opportunistic infections in patients suffering with AIDS (Tanaka et al., 2004). The crystal structures of pyrimethamine (Sethuraman & Thomas Muthiah, 2002) and 2-amino-4,6-dimethoxy pyrimidine have also been reported (Low et al., 2002). Hydrogen-bonding patterns in aminopyrimidine–carboxylate salts have been recently reviewed (Schwalbe & Cody, 2006). The crystal structures of 2-amino-4,6-dimethoxypyrimidinium 4-hydroxybenzoate monohydrate (Thanigaimani et al., 2007a) and 2-amino-4,6-dimethoxypyrimidinium salicylate (Thanigaimani et al., 2007b) have been reported by us. The present study was undertaken to obtain more information regarding patterns of hydrogen bonds in these types of compounds.

ORTEPII (Johnson, 1976) views of the title compounds, (I) and (II), are shown in Figs. 1 and 2, and selected geometric parameters are given in Tables 1 and 3. In (I), the asymmetric unit contains pairs of 2-amino-4,6-dimethoxypyrimidinium cations (A and B) and picrate anions (A and B). In (II), the asymmetric unit contains one protonated pyrimethaminium (PMN) cation, one picrate anion and one molecule of dimethyl sulfoxide (DMSO) solvate. In the two compounds, the pyrimidine rings are protonated at atom N1. Protonation of the pyrimidine base on the N1 site is reflected by an increase in bond angle at N1 [the C2—N1—C6 angle is 120.27 (16)° in cation A of (I), 120.44 (16)° in cation B of (I) and 121.51 (15)° in (II)] when compared with that at the unprotonated atom N3 [the C2—N3—C4 angle is 116.36 (17)° in cation A of (I), 116.42 (18)° in cation B of (I) and 117.92 (17)° in (II)]. The key conformational features of the PMN cations are described by two angles. The first is the dihedral angle between the 2,4-diaminopyrimidine and the 4-chlorophenyl mean planes. The second is the torsion angle that represents the deviation of the ethyl group from the pyrimidine plane. The dihedral angle between the pyrimidine and benzene ring is 81.05 (10)° and the C5—C6—C7—C8 torsion angle is -105.3 (2)°. These values are close to those observed in modeling studies of dihydrofolate reductase–pyrimethamine complexes, which indicates that these angles play an important role in the effective docking of the drug molecule in the active site of the enzyme (Sansom et al., 1989).

For ions A of (I), the phenolate O atom and two of the nitro O atoms (O9A and O4A) of the picrate anion form bifurcated N—H···O hydrogen bonds with the protonated pyrimidine and amine N atoms of the 2-amino-4,6-dimethoxypyrimidinium cation, forming three rings with graph-set notations R₁²(6), R₂¹(6) and R₁²(6) (Etter, 1990; Bernstein et al., 1995). A similar type of interaction has been observed in the crystal structure of 2-aminopyrimidinium picrate (Narayana et al., 2008). However, in cation B and compound (II), the protonated N atoms (N1B and N1) do not form bifurcated hydrogen bonds with the nitro group (N4B and N7) of the picrate anion, resulting in only two rings with graph-set notations R₂¹(6) and R₁²(6). This type of interaction has also been reported in the crystal structure of 2-amino-4,6-dimethylpyrimidinium picrate (Subashini et al., 2006). Ions A and B form individual chains via C—H···O hydrogen bonds. These two chains are interlinked by N—H···O hydrogen bonds to form a supramolecular sheet with graph-set notation R₆⁶(32) (Fig. 3).

In (II), the two inversion-related PMN cations are linked through a pair of N—H···N hydrogen bonds involving the 4-amino group and atom N3 of the pyrimidine ring, generating an R₂²(8) ring motif. No similar interactions are observed in (I). In addition to the pairing, the O atom from the DMSO solvent molecule bridges the 2-amino and 4-amino groups on either side of the paired bases, resulting in a self-complementary DADA (D represents a hydrogen-bond donor and A a hydrogen-bond acceptor) array of quadruple hydrogen-bonding patterns. The corresponding graph-set notations are R₃²(8), R₂²(8) and R₃²(8) (Fig. 4). This type of DADA array of quadruple hydrogen bonds has been observed in PMN carboxylates (Stanley et al., 2005).

In (I), π–π stacking interactions between the aromatic rings are also observed. The pyrimidine ring of 2-amino-4,6-dimethoxypyrimidinium (cation A) forms stacking interactions with the aryl rings of the picrate anion (A), with interplanar and centroid–centroid distances of 3.2953 (7) and 3.8433 (11) Å, respectively, and a slip angle (the angle between the centroid vector and the normal to the plane) of 30.97°. A similar type of stacking is also observed between the 2-amino-4,6-dimethoxypyrimidinium cation B, which forms stacking interactions with the aryl rings of the picrate anion A, with interplanar and centroid–centroid distances of 3.3652 (8) and 3.8659 (11) Å, respectively, the slip angle being 29.49°. These are typical aromatic stacking values (Hunter, 1994).

Related literature

For related literature, see: Atwal et al. (1989); Bernstein et al. (1995); Deetz et al. (2000); Desiraju (1989); Etter (1990); Harper et al. (2001); Hitchings & Burchall (1965); Hunter (1994); In et al. (1997); Johnson (1976); Low et al. (2002); Narayana et al. (2008); Sansom et al. (1989); Schwalbe & Cody (2006); Sethuraman & Muthiah (2002); Shriner et al. (1980); Stanley et al. (2005); Subashini et al. (2006); Tanaka et al. (2004); Thanigaimani et al. (2007a, 2007b); TranQui, Fresneau & Cussac (1998).

S2. Experimental

Compound (I) was prepared by mixing a hot methanol solution (20 ml) of 2-amino-4,6-dimethoxypyrimidine (38 mg) and picric acid (57 mg) and warming the solution for half an hour over a water bath. The solution was cooled slowly and kept at room temperature. After a few days, yellow plate-like crystals were obtained. Compound (II) was prepared by heating hot methanol solutions of pyrimethamine (62 mg, Shah Pharma Chemicals, India) and picric acid (57 mg, Merck) for 20 min; the solution became turbid. In order to obtain a clear solution, a few drops of DMSO was added. After about a week, thin yellow plates of (II) were obtained.

S3. Refinement

All H atoms were positioned geometrically and were treated as riding. The C—H and N—H bond lengths are 0.93–0.96 and 0.86 Å, respectively, for (I), and 0.95–0.99 and 0.88 Å, for (II). The constraint U_iso(H) = 1.2U_eq(carrier) or 1.5U_eq(methyl carrier) was applied as appropriate.

Computing details

Data collection: COLLECT (Hooft, 1998) for (I); CrysAlis CCD (Oxford Diffraction, 2007) for (II). Cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998) for (I); CrysAlis CCD (Oxford Diffraction, 2007) for (II). Data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998) for (I); CrysAlis RED (Oxford Diffraction, 2007 for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds.
	Fig. 2. The asymmetric unit of (II), showing 50% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds.
	Fig. 3. The crystal structure of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted. [Symmetry codes: (i) x + 1, y - 1, z; (ii) x, y, z - 1; (iii) x, y, z + 1.]
	Fig. 4. The crystal structure of (II). Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted. [Symmetry code: (i) -x, -y + 2, -z + 1.].

(I) 2-amino-4,6-dimethoxypyrimidinium 2,4,6-trinitrophenolate

Crystal data

C6H10N3O2^+·C6H2N3O7^−	Z = 4
Mr = 384.28	F(000) = 792
Triclinic, P1	Dx = 1.658 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8796 (2) Å	Cell parameters from 25 reflections
b = 13.2847 (3) Å	θ = 3.0–27.6°
c = 14.1395 (3) Å	µ = 0.14 mm^−1
α = 99.820 (1)°	T = 120 K
β = 100.701 (1)°	Plate-like, yellow
γ = 105.095 (1)°	0.16 × 0.12 × 0.06 mm
V = 1539.68 (6) Å^3

Data collection

Bruker–Nonius KappaCCD diffractometer	5725 reflections with I > 2σ(I)
Radiation source: Bruker–Nonius FR591 rotating anode	Rint = 0.039
Graphite monochromator	θmax = 27.6°, θmin = 3.0°
Detector resolution: 9.091 pixels mm^-1	h = −11→11
ϕ and ω scans	k = −17→17
27465 measured reflections	l = −17→18
7048 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0323P)^2 + 1.7779P] where P = (Fo^2 + 2Fc^2)/3
7048 reflections	(Δ/σ)max = 0.001
487 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

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 e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.51490 (17)	0.80162 (11)	0.49974 (10)	0.0239 (4)
O2A	0.24861 (17)	0.97367 (11)	0.70206 (10)	0.0221 (4)
N1A	0.38352 (19)	0.86439 (12)	0.75249 (11)	0.0181 (4)
N2A	0.5155 (2)	0.75255 (13)	0.81357 (12)	0.0224 (5)
N3A	0.51840 (19)	0.77285 (13)	0.65556 (12)	0.0203 (5)
C2A	0.4726 (2)	0.79610 (14)	0.73939 (14)	0.0182 (5)
C4A	0.4717 (2)	0.81982 (15)	0.58449 (14)	0.0199 (5)
C5A	0.3768 (2)	0.88854 (15)	0.59051 (14)	0.0204 (5)
C6A	0.3341 (2)	0.91031 (14)	0.67775 (14)	0.0184 (5)
C7A	0.6251 (3)	0.73974 (18)	0.49217 (16)	0.0280 (6)
C8A	0.1954 (3)	1.02904 (17)	0.62878 (15)	0.0266 (6)
O1B	0.97010 (17)	0.28292 (12)	1.24768 (10)	0.0257 (4)
O2B	0.76467 (17)	0.47940 (11)	1.03643 (10)	0.0231 (4)
N1B	0.90269 (19)	0.36924 (12)	0.99084 (12)	0.0190 (5)
N2B	1.0488 (2)	0.26189 (13)	0.93427 (12)	0.0217 (5)
N3B	1.0145 (2)	0.26976 (13)	1.09213 (12)	0.0215 (5)
C2B	0.9894 (2)	0.29994 (15)	1.00671 (14)	0.0189 (5)
C4B	0.9510 (2)	0.31102 (16)	1.16149 (14)	0.0212 (5)
C5B	0.8633 (2)	0.38392 (16)	1.15245 (14)	0.0217 (6)
C6B	0.8408 (2)	0.41204 (15)	1.06385 (14)	0.0192 (5)
C7B	1.0624 (3)	0.20959 (19)	1.26254 (16)	0.0308 (7)
C8B	0.6811 (3)	0.52224 (17)	1.10435 (16)	0.0270 (6)
O3A	0.40970 (17)	0.87674 (11)	0.94919 (10)	0.0223 (4)
O4A	0.2244 (2)	0.99548 (13)	0.89815 (10)	0.0336 (5)
O5A	0.1611 (2)	1.09046 (12)	1.01424 (11)	0.0321 (5)
O6A	0.16551 (19)	1.00919 (13)	1.32410 (11)	0.0328 (5)
O7A	0.28554 (19)	0.89623 (13)	1.36991 (10)	0.0319 (5)
O8A	0.6230 (2)	0.77922 (13)	1.17662 (12)	0.0390 (5)
O9A	0.52325 (19)	0.72863 (12)	1.01930 (11)	0.0308 (5)
N4A	0.21560 (19)	1.01815 (13)	0.98394 (12)	0.0201 (5)
N5A	0.2416 (2)	0.94539 (14)	1.30886 (12)	0.0244 (5)
N6A	0.5304 (2)	0.78063 (13)	1.10164 (12)	0.0234 (5)
C9A	0.3699 (2)	0.89222 (14)	1.02956 (13)	0.0180 (5)
C10A	0.2724 (2)	0.96016 (14)	1.05433 (13)	0.0180 (5)
C11A	0.2308 (2)	0.97693 (15)	1.14328 (14)	0.0195 (5)
C12A	0.2849 (2)	0.92743 (15)	1.21527 (14)	0.0204 (5)
C13A	0.3819 (2)	0.86228 (15)	1.20011 (14)	0.0206 (5)
C14A	0.4230 (2)	0.84649 (15)	1.11150 (14)	0.0195 (5)
O3B	0.89240 (17)	0.35722 (12)	0.79658 (10)	0.0249 (4)
O4B	0.6301 (3)	0.42205 (17)	0.81896 (14)	0.0529 (8)
O5B	0.6586 (2)	0.56976 (13)	0.76979 (13)	0.0383 (6)
O6B	0.6646 (2)	0.51986 (14)	0.42281 (12)	0.0448 (6)
O7B	0.80575 (19)	0.42411 (13)	0.36653 (11)	0.0317 (5)
O8B	1.02701 (19)	0.21778 (13)	0.55444 (11)	0.0312 (5)
O9B	1.0651 (2)	0.24881 (13)	0.71314 (11)	0.0344 (5)
N4B	0.6782 (2)	0.48144 (15)	0.76599 (12)	0.0265 (5)
N5B	0.7496 (2)	0.46085 (14)	0.43269 (12)	0.0252 (5)
N6B	1.00820 (19)	0.26385 (13)	0.63278 (12)	0.0227 (5)
C9B	0.8564 (2)	0.37611 (14)	0.71299 (14)	0.0185 (5)
C10B	0.7547 (2)	0.44294 (15)	0.69087 (14)	0.0198 (5)
C11B	0.7238 (2)	0.47285 (15)	0.60319 (14)	0.0210 (5)
C12B	0.7850 (2)	0.43321 (15)	0.52695 (14)	0.0205 (5)
C13B	0.8778 (2)	0.36448 (15)	0.53866 (14)	0.0196 (5)
C14B	0.9121 (2)	0.33741 (15)	0.62796 (14)	0.0192 (5)
H2A1	0.57240	0.70950	0.80760	0.0270*
H1A	0.35820	0.87870	0.80800	0.0220*
H2A2	0.48630	0.76730	0.86770	0.0270*
H7A1	0.64610	0.73270	0.42760	0.0420*
H7A2	0.57880	0.66990	0.50260	0.0420*
H7A3	0.72390	0.77530	0.54130	0.0420*
H5A	0.34460	0.91780	0.53790	0.0240*
H8A1	0.13450	1.07250	0.65450	0.0400*
H8A2	0.12910	0.97750	0.56990	0.0400*
H8A3	0.28710	1.07380	0.61340	0.0400*
H1B	0.88700	0.38600	0.93450	0.0230*
H5B	0.82280	0.41150	1.20380	0.0260*
H2B1	1.10340	0.21790	0.94230	0.0260*
H2B2	1.03290	0.28110	0.87910	0.0260*
H8B1	0.63080	0.56990	1.07660	0.0400*
H8B2	0.75640	0.56070	1.16600	0.0400*
H8B3	0.60060	0.46450	1.11550	0.0400*
H7B1	1.06670	0.19620	1.32750	0.0460*
H7B2	1.16950	0.24040	1.25620	0.0460*
H7B3	1.01240	0.14340	1.21380	0.0460*
H11A	0.16710	1.02100	1.15490	0.0230*
H13A	0.41810	0.83000	1.24940	0.0250*
H11B	0.66240	0.51920	0.59500	0.0250*
H13B	0.91640	0.33700	0.48640	0.0230*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0284 (7)	0.0308 (8)	0.0184 (7)	0.0158 (6)	0.0095 (6)	0.0064 (6)
O2A	0.0285 (7)	0.0253 (7)	0.0198 (7)	0.0165 (6)	0.0087 (6)	0.0082 (6)
N1A	0.0216 (8)	0.0196 (8)	0.0151 (7)	0.0086 (6)	0.0055 (6)	0.0042 (6)
N2A	0.0309 (9)	0.0240 (8)	0.0204 (8)	0.0168 (7)	0.0099 (7)	0.0092 (7)
N3A	0.0229 (8)	0.0210 (8)	0.0186 (8)	0.0081 (7)	0.0067 (6)	0.0050 (6)
C2A	0.0185 (9)	0.0157 (8)	0.0201 (9)	0.0048 (7)	0.0044 (7)	0.0039 (7)
C4A	0.0205 (9)	0.0207 (9)	0.0178 (9)	0.0053 (7)	0.0056 (7)	0.0034 (7)
C5A	0.0234 (10)	0.0214 (9)	0.0183 (9)	0.0091 (8)	0.0048 (7)	0.0064 (7)
C6A	0.0190 (9)	0.0166 (9)	0.0187 (9)	0.0053 (7)	0.0034 (7)	0.0033 (7)
C7A	0.0309 (11)	0.0362 (12)	0.0239 (10)	0.0191 (9)	0.0118 (9)	0.0059 (9)
C8A	0.0339 (11)	0.0299 (11)	0.0226 (10)	0.0193 (9)	0.0061 (9)	0.0093 (8)
O1B	0.0284 (8)	0.0339 (8)	0.0203 (7)	0.0145 (6)	0.0068 (6)	0.0120 (6)
O2B	0.0269 (7)	0.0237 (7)	0.0238 (7)	0.0135 (6)	0.0084 (6)	0.0072 (6)
N1B	0.0225 (8)	0.0201 (8)	0.0172 (8)	0.0089 (6)	0.0059 (6)	0.0069 (6)
N2B	0.0270 (9)	0.0225 (8)	0.0204 (8)	0.0137 (7)	0.0070 (7)	0.0067 (7)
N3B	0.0227 (8)	0.0239 (8)	0.0193 (8)	0.0086 (7)	0.0047 (7)	0.0064 (7)
C2B	0.0177 (9)	0.0186 (9)	0.0198 (9)	0.0056 (7)	0.0034 (7)	0.0038 (7)
C4B	0.0198 (9)	0.0238 (10)	0.0183 (9)	0.0040 (8)	0.0025 (7)	0.0064 (8)
C5B	0.0233 (10)	0.0241 (10)	0.0186 (9)	0.0077 (8)	0.0071 (8)	0.0045 (8)
C6B	0.0177 (9)	0.0165 (9)	0.0218 (9)	0.0032 (7)	0.0047 (7)	0.0031 (7)
C7B	0.0328 (12)	0.0387 (12)	0.0268 (11)	0.0161 (10)	0.0052 (9)	0.0167 (10)
C8B	0.0286 (11)	0.0282 (11)	0.0290 (11)	0.0157 (9)	0.0104 (9)	0.0043 (9)
O3A	0.0302 (7)	0.0243 (7)	0.0171 (6)	0.0135 (6)	0.0085 (6)	0.0061 (5)
O4A	0.0521 (10)	0.0445 (9)	0.0181 (7)	0.0312 (8)	0.0131 (7)	0.0128 (7)
O5A	0.0494 (10)	0.0332 (8)	0.0267 (8)	0.0287 (8)	0.0134 (7)	0.0110 (6)
O6A	0.0399 (9)	0.0391 (9)	0.0255 (8)	0.0159 (7)	0.0165 (7)	0.0081 (7)
O7A	0.0377 (9)	0.0408 (9)	0.0180 (7)	0.0094 (7)	0.0060 (6)	0.0139 (6)
O8A	0.0459 (10)	0.0406 (9)	0.0300 (8)	0.0262 (8)	−0.0072 (7)	0.0041 (7)
O9A	0.0441 (9)	0.0314 (8)	0.0242 (8)	0.0231 (7)	0.0088 (7)	0.0067 (6)
N4A	0.0225 (8)	0.0218 (8)	0.0187 (8)	0.0087 (7)	0.0061 (6)	0.0073 (6)
N5A	0.0255 (9)	0.0275 (9)	0.0173 (8)	0.0027 (7)	0.0053 (7)	0.0054 (7)
N6A	0.0272 (9)	0.0205 (8)	0.0234 (9)	0.0096 (7)	0.0031 (7)	0.0067 (7)
C9A	0.0192 (9)	0.0162 (8)	0.0176 (9)	0.0049 (7)	0.0033 (7)	0.0031 (7)
C10A	0.0198 (9)	0.0173 (9)	0.0168 (9)	0.0058 (7)	0.0021 (7)	0.0058 (7)
C11A	0.0190 (9)	0.0187 (9)	0.0195 (9)	0.0040 (7)	0.0045 (7)	0.0036 (7)
C12A	0.0211 (9)	0.0219 (9)	0.0149 (9)	0.0013 (8)	0.0040 (7)	0.0038 (7)
C13A	0.0225 (9)	0.0183 (9)	0.0182 (9)	0.0031 (7)	−0.0001 (7)	0.0069 (7)
C14A	0.0224 (9)	0.0161 (9)	0.0199 (9)	0.0062 (7)	0.0038 (7)	0.0046 (7)
O3B	0.0318 (8)	0.0303 (8)	0.0188 (7)	0.0167 (6)	0.0078 (6)	0.0090 (6)
O4B	0.0732 (14)	0.0752 (14)	0.0490 (11)	0.0519 (12)	0.0435 (10)	0.0388 (11)
O5B	0.0463 (10)	0.0317 (9)	0.0428 (10)	0.0229 (8)	0.0161 (8)	0.0008 (7)
O6B	0.0776 (13)	0.0464 (10)	0.0266 (8)	0.0428 (10)	0.0118 (8)	0.0147 (8)
O7B	0.0380 (9)	0.0420 (9)	0.0190 (7)	0.0135 (7)	0.0118 (6)	0.0094 (7)
O8B	0.0371 (9)	0.0359 (8)	0.0291 (8)	0.0220 (7)	0.0149 (7)	0.0054 (7)
O9B	0.0411 (9)	0.0403 (9)	0.0255 (8)	0.0273 (8)	−0.0010 (7)	0.0040 (7)
N4B	0.0292 (9)	0.0365 (10)	0.0190 (8)	0.0199 (8)	0.0054 (7)	0.0054 (7)
N5B	0.0337 (10)	0.0231 (8)	0.0188 (8)	0.0083 (7)	0.0057 (7)	0.0057 (7)
N6B	0.0209 (8)	0.0231 (8)	0.0246 (9)	0.0090 (7)	0.0052 (7)	0.0039 (7)
C9B	0.0206 (9)	0.0167 (9)	0.0175 (9)	0.0047 (7)	0.0040 (7)	0.0041 (7)
C10B	0.0223 (9)	0.0209 (9)	0.0175 (9)	0.0096 (8)	0.0052 (7)	0.0026 (7)
C11B	0.0247 (10)	0.0187 (9)	0.0205 (9)	0.0098 (8)	0.0035 (8)	0.0041 (7)
C12B	0.0237 (10)	0.0198 (9)	0.0173 (9)	0.0059 (8)	0.0039 (7)	0.0047 (7)
C13B	0.0195 (9)	0.0183 (9)	0.0194 (9)	0.0032 (7)	0.0066 (7)	0.0024 (7)
C14B	0.0190 (9)	0.0183 (9)	0.0222 (9)	0.0082 (7)	0.0059 (7)	0.0045 (7)

Geometric parameters (Å, º)

O1A—C4A	1.327 (2)	N5A—C12A	1.444 (3)
O1A—C7A	1.440 (3)	N6A—C14A	1.462 (3)
O2A—C6A	1.317 (2)	N4B—C10B	1.454 (3)
O2A—C8A	1.448 (3)	N5B—C12B	1.443 (3)
O1B—C7B	1.445 (3)	N6B—C14B	1.457 (3)
O1B—C4B	1.328 (2)	C4A—C5A	1.397 (3)
O2B—C6B	1.321 (2)	C5A—C6A	1.363 (3)
O2B—C8B	1.447 (3)	C5A—H5A	0.9300
O3A—C9A	1.251 (2)	C7A—H7A2	0.9600
O4A—N4A	1.221 (2)	C7A—H7A1	0.9600
O5A—N4A	1.233 (2)	C7A—H7A3	0.9600
O6A—N5A	1.229 (3)	C8A—H8A3	0.9600
O7A—N5A	1.234 (2)	C8A—H8A1	0.9600
O8A—N6A	1.221 (2)	C8A—H8A2	0.9600
O9A—N6A	1.230 (2)	C4B—C5B	1.400 (3)
O3B—C9B	1.251 (2)	C5B—C6B	1.362 (3)
O4B—N4B	1.229 (3)	C5B—H5B	0.9300
O5B—N4B	1.224 (3)	C7B—H7B3	0.9600
O6B—N5B	1.229 (3)	C7B—H7B2	0.9600
O7B—N5B	1.227 (2)	C7B—H7B1	0.9600
O8B—N6B	1.233 (2)	C8B—H8B3	0.9600
O9B—N6B	1.226 (2)	C8B—H8B2	0.9600
N1A—C2A	1.362 (3)	C8B—H8B1	0.9600
N1A—C6A	1.367 (2)	C9A—C14A	1.456 (3)
N2A—C2A	1.324 (3)	C9A—C10A	1.449 (3)
N3A—C4A	1.329 (3)	C10A—C11A	1.374 (3)
N3A—C2A	1.336 (3)	C11A—C12A	1.382 (3)
N1A—H1A	0.8600	C12A—C13A	1.389 (3)
N2A—H2A1	0.8600	C13A—C14A	1.366 (3)
N2A—H2A2	0.8600	C11A—H11A	0.9300
N1B—C6B	1.365 (3)	C13A—H13A	0.9300
N1B—C2B	1.366 (3)	C9B—C10B	1.452 (3)
N2B—C2B	1.321 (3)	C9B—C14B	1.448 (3)
N3B—C2B	1.335 (3)	C10B—C11B	1.367 (3)
N3B—C4B	1.328 (3)	C11B—C12B	1.381 (3)
N1B—H1B	0.8600	C12B—C13B	1.390 (3)
N2B—H2B1	0.8600	C13B—C14B	1.373 (3)
N2B—H2B2	0.8600	C11B—H11B	0.9300
N4A—C10A	1.455 (2)	C13B—H13B	0.9300
O1A···O7A^i	3.135 (2)	N3A···H7A2	2.5800
O1B···N1A^ii	3.238 (2)	N3B···H7B3	2.6000
O1B···O7B^iii	3.120 (2)	N3B···H7B2	2.6100
O2A···O8A^iv	3.228 (2)	C2A···O3A	3.178 (2)
O2A···C7B^ii	3.351 (3)	C2A···O7B^viii	3.206 (3)
O2A···O4A	2.792 (2)	C2A···C11A^iv	3.364 (3)
O2A···C13A^iv	3.315 (2)	C2B···C10A^ii	3.485 (3)
O2B···O4B	2.971 (2)	C2B···C14A^ii	3.591 (3)
O2B···C2B^v	3.392 (2)	C2B···O2B^v	3.392 (2)
O2B···O9A^ii	3.102 (2)	C2B···C9A^ii	3.415 (3)
O2B···N1B^v	3.242 (2)	C2B···O3B	3.211 (2)
O3A···O4A	2.649 (2)	C4A···C13B^viii	3.353 (3)
O3A···C2A	3.178 (2)	C4A···C12B^viii	3.442 (3)
O3A···N2A	2.771 (2)	C4A···O6A^iv	3.294 (3)
O3A···O9A	2.683 (2)	C4A···N5A^iv	3.364 (3)
O3A···N1A	2.720 (2)	C4B···O5B^v	3.292 (3)
O3A···C10A^iv	3.093 (2)	C4B···O3A^ii	3.402 (2)
O3A···N4A	2.903 (2)	C5A···O7A^i	3.100 (2)
O3A···N6A	2.867 (2)	C5A···N5A^iv	3.409 (3)
O3A···O3A^iv	3.188 (2)	C5A···C13B^viii	3.487 (3)
O3A···N4A^iv	3.143 (2)	C5B···O7B^iii	3.142 (2)
O3A···C4B^ii	3.402 (2)	C5B···C9B^v	3.467 (3)
O3A···C9A^iv	3.111 (2)	C6A···C12A^iv	3.401 (3)
O3B···C13A^ii	3.291 (3)	C6A···C13A^iv	3.332 (3)
O3B···N4B	2.846 (2)	C6B···O3B^v	3.365 (2)
O3B···N2B	2.842 (2)	C6B···O9A^ii	3.165 (3)
O3B···C6B^v	3.365 (2)	C7A···O8B^ix	3.205 (3)
O3B···N1B	2.707 (2)	C7A···O6B	3.050 (3)
O3B···N6B	2.920 (2)	C7A···C11B^viii	3.462 (3)
O3B···C2B	3.211 (2)	C7B···O4A^ii	3.346 (3)
O3B···O4B	2.737 (3)	C7B···O6A^x	3.232 (3)
O3B···O9B	2.657 (2)	C7B···O2A^ii	3.351 (3)
O4A···O2A	2.792 (2)	C8A···O6A^vi	3.322 (3)
O4A···N6A^iv	3.195 (2)	C8A···O8A^iv	3.238 (3)
O4A···C9A^iv	3.400 (3)	C8B···N2B^v	3.422 (3)
O4A···C14A^iv	3.326 (3)	C8B···O9A^ii	3.338 (3)
O4A···O3A	2.649 (2)	C8B···O4B^ii	3.356 (4)
O4A···N1A	3.226 (2)	C9A···C9A^iv	3.511 (3)
O4A···C7B^ii	3.346 (3)	C9A···C2B^ii	3.415 (3)
O4B···O8A^ii	3.030 (3)	C9A···O4A^iv	3.400 (3)
O4B···O3B	2.737 (3)	C9A···O3A^iv	3.111 (2)
O4B···O2B	2.971 (2)	C9B···C5B^v	3.467 (3)
O4B···C8B^ii	3.356 (4)	C9B···O7A^ii	3.418 (2)
O4B···N6A^ii	3.189 (3)	C10A···O3A^iv	3.093 (2)
O5A···O5A^vi	3.128 (2)	C10A···C2B^ii	3.485 (3)
O5A···N2B^vii	3.017 (2)	C11A···N2B^ii	3.336 (3)
O5A···N3B^vii	3.136 (2)	C11A···C2A^iv	3.364 (3)
O5B···C4B^v	3.292 (3)	C11A···N1A^iv	3.413 (3)
O5B···N2A	3.047 (3)	C11B···C7A^viii	3.462 (3)
O5B···N3B^v	3.168 (2)	C12A···N2B^ii	3.399 (3)
O6A···C7B^vii	3.232 (3)	C12A···N1A^iv	3.370 (3)
O6A···C4A^iv	3.294 (3)	C12A···C6A^iv	3.401 (3)
O6A···C8A^vi	3.322 (3)	C12B···C4A^viii	3.442 (3)
O6B···C7A	3.050 (3)	C13A···C6A^iv	3.332 (3)
O7A···C5A^iii	3.100 (2)	C13A···O3B^ii	3.291 (3)
O7A···N6B^ii	2.894 (2)	C13A···O2A^iv	3.315 (2)
O7A···O9B^ii	3.087 (2)	C13B···C4A^viii	3.353 (3)
O7A···O1A^iii	3.135 (2)	C13B···O7B^ix	3.284 (3)
O7A···C14B^ii	3.151 (3)	C13B···N5B^ix	3.417 (3)
O7A···C9B^ii	3.418 (2)	C13B···C5A^viii	3.487 (3)
O7B···O1B^i	3.120 (2)	C14A···O4A^iv	3.326 (3)
O7B···C5B^i	3.142 (2)	C14A···C2B^ii	3.591 (3)
O7B···C2A^viii	3.206 (3)	C14A···N1B^ii	3.374 (3)
O7B···C13B^ix	3.284 (3)	C14B···O7A^ii	3.151 (3)
O8A···O2A^iv	3.228 (2)	C5A···H8A3	2.7600
O8A···O4B^ii	3.030 (3)	C5A···H8A2	2.7500
O8A···O9B^v	3.061 (3)	C5B···H8B2	2.7400
O8A···C8A^iv	3.238 (3)	C5B···H8B3	2.8100
O8B···C7A^ix	3.205 (3)	C7B···H7A3^v	3.0000
O9A···C6B^ii	3.165 (3)	C8A···H5A	2.5700
O9A···N2A	2.970 (2)	C8B···H5B	2.6000
O9A···C8B^ii	3.338 (3)	C8B···H2B2^v	3.0700
O9A···O3A	2.683 (2)	C9A···H1A	3.0900
O9A···O2B^ii	3.102 (2)	C9A···H2A2	3.0900
O9B···O8A^v	3.061 (3)	C9B···H1B	3.0700
O9B···N5A^ii	3.150 (3)	C11B···H7A2^viii	2.8200
O9B···O3B	2.657 (2)	C12B···H7A2^viii	3.0800
O9B···O7A^ii	3.087 (2)	H2A1···O5B	2.2100
O9B···N2B	3.134 (2)	H2A1···H7B2^v	2.5900
O3A···H2A2	2.0300	H1A···H2A2	2.2700
O3A···H1A	1.9700	H1A···O3A	1.9700
O3B···H2B2	2.1100	H1A···C9A	3.0900
O3B···H1B	1.9300	H1A···O4A	2.5100
O4A···H7B3^ii	2.4700	H1B···H2B2	2.2800
O4A···H1A	2.5100	H1B···O3B	1.9300
O4B···H1B	2.7500	H1B···O4B	2.7500
O5A···H2B1^vii	2.2400	H1B···C9B	3.0700
O5A···H11A	2.3300	H2A2···O9A	2.2700
O5B···H7B2^v	2.7100	H2A2···C9A	3.0900
O5B···H2A1	2.2100	H2A2···O3A	2.0300
O5B···H11B	2.4600	H2A2···H1A	2.2700
O6A···H7B1^vii	2.8400	H7A1···O8B^ix	2.7600
O6A···H11A	2.4300	H7A1···O6B	2.8600
O6A···H8A1^vi	2.7000	H7A2···C11B^viii	2.8200
O6B···H7A1	2.8600	H7A2···N3A	2.5800
O6B···H7A2	2.4800	H7A2···O6B	2.4800
O6B···H11B^viii	2.7700	H7A2···C12B^viii	3.0800
O6B···H11B	2.4400	H7A3···O8B^ix	2.7900
O7A···H5A^iii	2.2900	H7A3···N3A	2.6500
O7A···H13A	2.4200	H7A3···H7B1^v	2.2700
O7B···H5B^i	2.3100	H7A3···C7B^v	3.0000
O7B···H13B	2.4100	H5A···H8A2	2.3400
O8A···H13A	2.4300	H5A···H8A3	2.3900
O8A···H8A1^iv	2.9100	H5A···C8A	2.5700
O8B···H13B	2.3200	H5A···O7A^i	2.2900
O8B···H7A1^ix	2.7600	H5B···C8B	2.6000
O8B···H8A1^x	2.8300	H5B···O7B^iii	2.3100
O8B···H8A2^viii	2.7200	H5B···H8B3	2.4600
O8B···H7A3^ix	2.7900	H5B···H8B2	2.3300
O9A···H8B3^ii	2.7400	H8A1···O8B^vii	2.8300
O9A···H8B1	2.7100	H8A1···O9B^vii	2.6100
O9A···H2A2	2.2700	H8A1···O8A^iv	2.9100
O9B···H8A1^x	2.6100	H8A1···O6A^vi	2.7000
O9B···H2B2	2.4000	H8A2···O8B^viii	2.7200
O9B···H8B2^v	2.7000	H8A2···H5A	2.3400
N1A···C12A^iv	3.370 (3)	H8A2···C5A	2.7500
N1A···O4A	3.226 (2)	H8A3···H5A	2.3900
N1A···O1B^ii	3.238 (2)	H8A3···C5A	2.7600
N1A···O3A	2.720 (2)	H2B1···O5A^x	2.2400
N1A···C11A^iv	3.413 (3)	H2B2···H1B	2.2800
N1B···O3B	2.707 (2)	H2B2···C8B^v	3.0700
N1B···C14A^ii	3.374 (3)	H2B2···O3B	2.1100
N1B···O2B^v	3.242 (2)	H2B2···O9B	2.4000
N2A···O5B	3.047 (3)	H8B1···O9A	2.7100
N2A···O9A	2.970 (2)	H11A···O5A	2.3300
N2A···O3A	2.771 (2)	H11A···O6A	2.4300
N2B···C11A^ii	3.336 (3)	H11A···H7B3^vii	2.5200
N2B···C12A^ii	3.399 (3)	H11B···O6B^viii	2.7700
N2B···O5A^x	3.017 (2)	H11B···O5B	2.4600
N2B···O9B	3.134 (2)	H11B···O6B	2.4400
N2B···C8B^v	3.422 (3)	H8B2···C5B	2.7400
N2B···O3B	2.842 (2)	H8B2···H5B	2.3300
N3A···N5B^viii	3.254 (2)	H8B2···O9B^v	2.7000
N3B···O5A^x	3.136 (2)	H8B3···O9A^ii	2.7400
N3B···O5B^v	3.168 (2)	H8B3···H5B	2.4600
N4A···O3A	2.903 (2)	H8B3···C5B	2.8100
N4A···O3A^iv	3.143 (2)	H13A···O8A	2.4300
N4B···O3B	2.846 (2)	H13A···O7A	2.4200
N5A···C4A^iv	3.364 (3)	H13B···O7B	2.4100
N5A···O9B^ii	3.150 (3)	H13B···O8B	2.3200
N5A···C5A^iv	3.409 (3)	H7B1···O6A^x	2.8400
N5B···C13B^ix	3.417 (3)	H7B1···H7A3^v	2.2700
N5B···N3A^viii	3.254 (2)	H7B2···O5B^v	2.7100
N6A···O4B^ii	3.189 (3)	H7B2···N3A^v	2.8800
N6A···O4A^iv	3.195 (2)	H7B2···H2A1^v	2.5900
N6A···O3A	2.867 (2)	H7B2···N3B	2.6100
N6B···O7A^ii	2.894 (2)	H7B3···H11A^x	2.5200
N6B···O3B	2.920 (2)	H7B3···O4A^ii	2.4700
N3A···H7B2^v	2.8800	H7B3···N3B	2.6000
N3A···H7A3	2.6500
C4A—O1A—C7A	118.07 (16)	N1B—C2B—N3B	122.09 (17)
C6A—O2A—C8A	116.82 (16)	N1B—C2B—N2B	118.18 (17)
C4B—O1B—C7B	118.15 (16)	N2B—C2B—N3B	119.73 (18)
C6B—O2B—C8B	117.07 (16)	O1B—C4B—N3B	119.22 (18)
C2A—N1A—C6A	120.27 (16)	N3B—C4B—C5B	125.39 (18)
C2A—N3A—C4A	116.36 (17)	O1B—C4B—C5B	115.39 (17)
C2A—N1A—H1A	120.00	C4B—C5B—C6B	115.91 (17)
C6A—N1A—H1A	120.00	N1B—C6B—C5B	119.72 (18)
C2A—N2A—H2A1	120.00	O2B—C6B—C5B	128.18 (18)
C2A—N2A—H2A2	120.00	O2B—C6B—N1B	112.10 (16)
H2A1—N2A—H2A2	120.00	C6B—C5B—H5B	122.00
C2B—N1B—C6B	120.44 (16)	C4B—C5B—H5B	122.00
C2B—N3B—C4B	116.42 (18)	H7B1—C7B—H7B2	109.00
C6B—N1B—H1B	120.00	H7B2—C7B—H7B3	109.00
C2B—N1B—H1B	120.00	O1B—C7B—H7B1	109.00
C2B—N2B—H2B1	120.00	O1B—C7B—H7B2	109.00
H2B1—N2B—H2B2	120.00	H7B1—C7B—H7B3	110.00
C2B—N2B—H2B2	120.00	O1B—C7B—H7B3	109.00
O4A—N4A—O5A	122.05 (17)	O2B—C8B—H8B1	109.00
O4A—N4A—C10A	120.06 (17)	O2B—C8B—H8B2	110.00
O5A—N4A—C10A	117.88 (16)	H8B1—C8B—H8B3	109.00
O6A—N5A—C12A	118.81 (17)	H8B2—C8B—H8B3	109.00
O6A—N5A—O7A	123.62 (17)	O2B—C8B—H8B3	109.00
O7A—N5A—C12A	117.57 (17)	H8B1—C8B—H8B2	109.00
O8A—N6A—C14A	117.93 (17)	C10A—C9A—C14A	111.85 (16)
O8A—N6A—O9A	122.85 (19)	O3A—C9A—C10A	124.91 (17)
O9A—N6A—C14A	119.23 (17)	O3A—C9A—C14A	123.19 (17)
O4B—N4B—O5B	123.5 (2)	N4A—C10A—C11A	115.75 (17)
O4B—N4B—C10B	118.6 (2)	C9A—C10A—C11A	124.16 (17)
O5B—N4B—C10B	117.79 (18)	N4A—C10A—C9A	120.06 (16)
O6B—N5B—C12B	118.27 (17)	C10A—C11A—C12A	119.15 (18)
O7B—N5B—C12B	118.31 (17)	N5A—C12A—C13A	119.39 (17)
O6B—N5B—O7B	123.42 (18)	C11A—C12A—C13A	121.49 (18)
O8B—N6B—O9B	122.55 (18)	N5A—C12A—C11A	119.12 (17)
O9B—N6B—C14B	119.59 (17)	C12A—C13A—C14A	118.85 (18)
O8B—N6B—C14B	117.86 (16)	C9A—C14A—C13A	124.46 (18)
N1A—C2A—N2A	117.92 (17)	N6A—C14A—C13A	116.17 (17)
N1A—C2A—N3A	122.45 (17)	N6A—C14A—C9A	119.36 (16)
N2A—C2A—N3A	119.63 (18)	C10A—C11A—H11A	120.00
O1A—C4A—N3A	119.61 (17)	C12A—C11A—H11A	120.00
O1A—C4A—C5A	115.34 (17)	C14A—C13A—H13A	121.00
N3A—C4A—C5A	125.05 (18)	C12A—C13A—H13A	121.00
C4A—C5A—C6A	116.34 (17)	O3B—C9B—C10B	123.01 (17)
N1A—C6A—C5A	119.50 (17)	O3B—C9B—C14B	125.19 (18)
O2A—C6A—C5A	127.78 (18)	C10B—C9B—C14B	111.79 (16)
O2A—C6A—N1A	112.72 (16)	N4B—C10B—C9B	118.81 (17)
C6A—C5A—H5A	122.00	N4B—C10B—C11B	116.48 (17)
C4A—C5A—H5A	122.00	C9B—C10B—C11B	124.71 (17)
O1A—C7A—H7A1	109.00	C10B—C11B—C12B	119.03 (18)
H7A1—C7A—H7A2	109.00	N5B—C12B—C11B	120.02 (17)
O1A—C7A—H7A2	110.00	N5B—C12B—C13B	119.01 (17)
H7A2—C7A—H7A3	109.00	C11B—C12B—C13B	120.95 (18)
O1A—C7A—H7A3	109.00	C12B—C13B—C14B	119.57 (18)
H7A1—C7A—H7A3	109.00	N6B—C14B—C9B	120.55 (16)
O2A—C8A—H8A2	109.00	N6B—C14B—C13B	115.63 (17)
O2A—C8A—H8A3	110.00	C9B—C14B—C13B	123.81 (18)
H8A1—C8A—H8A3	109.00	C10B—C11B—H11B	120.00
H8A2—C8A—H8A3	110.00	C12B—C11B—H11B	121.00
O2A—C8A—H8A1	109.00	C12B—C13B—H13B	120.00
H8A1—C8A—H8A2	109.00	C14B—C13B—H13B	120.00
C7A—O1A—C4A—N3A	−6.2 (3)	O8B—N6B—C14B—C9B	166.64 (18)
C7A—O1A—C4A—C5A	174.24 (18)	O8B—N6B—C14B—C13B	−12.3 (3)
C8A—O2A—C6A—N1A	177.91 (17)	O9B—N6B—C14B—C13B	168.64 (18)
C8A—O2A—C6A—C5A	−1.3 (3)	O9B—N6B—C14B—C9B	−12.4 (3)
C7B—O1B—C4B—C5B	−178.73 (18)	O1A—C4A—C5A—C6A	−178.55 (17)
C7B—O1B—C4B—N3B	1.1 (3)	N3A—C4A—C5A—C6A	2.0 (3)
C8B—O2B—C6B—N1B	174.40 (17)	C4A—C5A—C6A—N1A	−0.6 (3)
C8B—O2B—C6B—C5B	−6.3 (3)	C4A—C5A—C6A—O2A	178.61 (19)
C6A—N1A—C2A—N3A	1.5 (3)	O1B—C4B—C5B—C6B	−179.02 (18)
C2A—N1A—C6A—O2A	179.66 (16)	N3B—C4B—C5B—C6B	1.2 (3)
C2A—N1A—C6A—C5A	−1.0 (3)	C4B—C5B—C6B—N1B	0.0 (3)
C6A—N1A—C2A—N2A	−179.05 (17)	C4B—C5B—C6B—O2B	−179.27 (19)
C4A—N3A—C2A—N1A	−0.3 (3)	O3A—C9A—C10A—N4A	−1.2 (3)
C4A—N3A—C2A—N2A	−179.68 (18)	O3A—C9A—C14A—C13A	179.79 (19)
C2A—N3A—C4A—O1A	179.01 (17)	C10A—C9A—C14A—N6A	−176.52 (16)
C2A—N3A—C4A—C5A	−1.5 (3)	C10A—C9A—C14A—C13A	2.1 (3)
C6B—N1B—C2B—N2B	−179.02 (18)	O3A—C9A—C10A—C11A	−179.48 (19)
C6B—N1B—C2B—N3B	1.3 (3)	C14A—C9A—C10A—N4A	176.45 (16)
C2B—N1B—C6B—O2B	178.21 (17)	C14A—C9A—C10A—C11A	−1.9 (3)
C2B—N1B—C6B—C5B	−1.2 (3)	O3A—C9A—C14A—N6A	1.2 (3)
C2B—N3B—C4B—C5B	−1.1 (3)	N4A—C10A—C11A—C12A	−177.85 (17)
C4B—N3B—C2B—N1B	−0.2 (3)	C9A—C10A—C11A—C12A	0.5 (3)
C4B—N3B—C2B—N2B	−179.86 (18)	C10A—C11A—C12A—N5A	179.79 (18)
C2B—N3B—C4B—O1B	179.13 (18)	C10A—C11A—C12A—C13A	0.8 (3)
O5A—N4A—C10A—C11A	12.5 (3)	N5A—C12A—C13A—C14A	−179.54 (18)
O5A—N4A—C10A—C9A	−165.94 (18)	C11A—C12A—C13A—C14A	−0.6 (3)
O4A—N4A—C10A—C11A	−168.31 (18)	C12A—C13A—C14A—C9A	−1.0 (3)
O4A—N4A—C10A—C9A	13.2 (3)	C12A—C13A—C14A—N6A	177.66 (17)
O6A—N5A—C12A—C11A	−4.2 (3)	O3B—C9B—C10B—N4B	−6.2 (3)
O7A—N5A—C12A—C11A	176.75 (18)	O3B—C9B—C10B—C11B	174.15 (19)
O6A—N5A—C12A—C13A	174.82 (19)	C14B—C9B—C10B—N4B	175.18 (17)
O7A—N5A—C12A—C13A	−4.3 (3)	C14B—C9B—C10B—C11B	−4.5 (3)
O9A—N6A—C14A—C9A	−29.8 (3)	O3B—C9B—C14B—N6B	5.0 (3)
O8A—N6A—C14A—C13A	−28.0 (3)	O3B—C9B—C14B—C13B	−176.17 (19)
O9A—N6A—C14A—C13A	151.42 (19)	C10B—C9B—C14B—N6B	−176.42 (17)
O8A—N6A—C14A—C9A	150.80 (19)	C10B—C9B—C14B—C13B	2.5 (3)
O4B—N4B—C10B—C11B	143.1 (2)	N4B—C10B—C11B—C12B	−175.99 (18)
O4B—N4B—C10B—C9B	−36.6 (3)	C9B—C10B—C11B—C12B	3.7 (3)
O5B—N4B—C10B—C9B	146.74 (19)	C10B—C11B—C12B—N5B	177.97 (18)
O5B—N4B—C10B—C11B	−33.5 (3)	C10B—C11B—C12B—C13B	−0.5 (3)
O6B—N5B—C12B—C13B	178.48 (19)	N5B—C12B—C13B—C14B	−179.89 (18)
O7B—N5B—C12B—C11B	−179.90 (19)	C11B—C12B—C13B—C14B	−1.4 (3)
O6B—N5B—C12B—C11B	0.0 (3)	C12B—C13B—C14B—N6B	179.19 (17)
O7B—N5B—C12B—C13B	−1.4 (3)	C12B—C13B—C14B—C9B	0.3 (3)

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+2; (iii) x, y, z+1; (iv) −x+1, −y+2, −z+2; (v) −x+2, −y+1, −z+2; (vi) −x, −y+2, −z+2; (vii) x−1, y+1, z; (viii) −x+1, −y+1, −z+1; (ix) −x+2, −y+1, −z+1; (x) x+1, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A1···O5B	0.86	2.21	3.047 (3)	165
N1A—H1A···O3A	0.86	1.97	2.720 (2)	145
N1A—H1A···O4A	0.86	2.51	3.226 (2)	142
N1B—H1B···O3B	0.86	1.93	2.707 (2)	149
N2A—H2A2···O3A	0.86	2.03	2.771 (2)	143
N2A—H2A2···O9A	0.86	2.27	2.970 (2)	138
N2B—H2B1···O5A^x	0.86	2.24	3.017 (2)	151
N2B—H2B2···O3B	0.86	2.11	2.842 (2)	142
N2B—H2B2···O9B	0.86	2.40	3.134 (2)	144
C7A—H7A2···O6B	0.96	2.48	3.050 (3)	118
C5A—H5A···O7A^i	0.93	2.29	3.100 (2)	146
C5B—H5B···O7B^iii	0.93	2.31	3.142 (2)	148
C13B—H13B···O8B	0.93	2.32	2.643 (3)	100
C7B—H7B3···O4A^ii	0.96	2.47	3.346 (3)	152

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

(II) 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 2,4,6-trinitrophenolate dimethyl sulfoxide solvate

Crystal data

C12H14ClN4^+·C6H2N3O7^−·C2H6OS	Z = 2
Mr = 555.97	F(000) = 576
Triclinic, P1	Dx = 1.488 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3365 (3) Å	Cell parameters from 5230 reflections
b = 11.1245 (3) Å	θ = 4.7–32.5°
c = 13.1861 (6) Å	µ = 0.30 mm^−1
α = 83.779 (3)°	T = 200 K
β = 86.057 (3)°	Thin plate, yellow
γ = 65.784 (3)°	0.47 × 0.26 × 0.21 mm
V = 1241.24 (8) Å^3

Data collection

Oxford Diffraction Gemini diffractometer	7722 independent reflections
Radiation source: fine-focus sealed tube	3648 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.5081 pixels mm^-1	θmax = 32.5°, θmin = 4.7°
ϕ and ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −16→16
Tmin = 0.873, Tmax = 0.940	l = −18→18
17314 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0964P)^2] where P = (Fo^2 + 2Fc^2)/3
7722 reflections	(Δ/σ)max < 0.001
337 parameters	Δρmax = 1.09 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Special details

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 e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.49545 (10)	1.25570 (7)	1.03419 (6)	0.0741 (3)
N1	0.04367 (19)	0.65153 (14)	0.68692 (13)	0.0300 (5)
N2	0.1285 (2)	0.62637 (15)	0.51928 (14)	0.0354 (5)
N3	0.01798 (18)	0.83630 (14)	0.57234 (12)	0.0267 (5)
N4	−0.1031 (2)	1.04340 (15)	0.62414 (14)	0.0350 (5)
C2	0.0633 (2)	0.70600 (17)	0.59243 (16)	0.0280 (6)
C4	−0.0571 (2)	0.91427 (17)	0.64708 (15)	0.0263 (6)
C5	−0.0888 (2)	0.86338 (17)	0.74662 (15)	0.0274 (6)
C6	−0.0322 (2)	0.72887 (18)	0.76506 (16)	0.0288 (6)
C7	−0.0394 (3)	0.65738 (19)	0.86671 (17)	0.0367 (7)
C8	0.1217 (4)	0.5947 (3)	0.9150 (2)	0.0603 (10)
C9	−0.1858 (2)	0.95619 (17)	0.82243 (16)	0.0288 (6)
C10	−0.3450 (3)	0.9860 (2)	0.83238 (18)	0.0391 (7)
C11	−0.4400 (3)	1.0766 (2)	0.89940 (19)	0.0450 (8)
C12	−0.3751 (3)	1.1391 (2)	0.95326 (18)	0.0417 (7)
C13	−0.2182 (3)	1.1117 (2)	0.94463 (18)	0.0426 (8)
C14	−0.1241 (3)	1.0199 (2)	0.87874 (17)	0.0364 (7)
O1	0.1807 (2)	0.38568 (13)	0.63821 (13)	0.0454 (5)
O2	0.2569 (2)	0.37218 (15)	0.44071 (14)	0.0606 (7)
O3	0.33344 (18)	0.18669 (15)	0.37755 (13)	0.0432 (5)
O4	0.37476 (19)	−0.20571 (14)	0.56383 (15)	0.0497 (6)
O5	0.3080 (2)	−0.21088 (15)	0.72474 (16)	0.0564 (7)
O6	0.1320 (3)	0.17625 (18)	0.89968 (16)	0.0745 (8)
O7	0.0568 (4)	0.36318 (19)	0.81994 (19)	0.1141 (12)
N5	0.2881 (2)	0.25411 (16)	0.45062 (15)	0.0356 (6)
N6	0.3286 (2)	−0.15297 (17)	0.64315 (18)	0.0432 (7)
N7	0.1278 (2)	0.24445 (18)	0.82258 (16)	0.0455 (7)
C15	0.2111 (2)	0.26641 (18)	0.63843 (17)	0.0319 (6)
C16	0.2716 (2)	0.18969 (18)	0.54984 (17)	0.0310 (6)
C17	0.3082 (2)	0.05632 (18)	0.55230 (18)	0.0332 (6)
C18	0.2924 (2)	−0.01241 (18)	0.64287 (19)	0.0350 (7)
C19	0.2366 (2)	0.05040 (19)	0.73040 (18)	0.0354 (7)
C20	0.1952 (2)	0.18444 (18)	0.72822 (17)	0.0336 (6)
S1	0.37172 (8)	0.63702 (5)	0.26014 (5)	0.0498 (2)
O8	0.2139 (2)	0.70534 (14)	0.31069 (13)	0.0484 (5)
C21	0.4995 (4)	0.5393 (3)	0.3597 (2)	0.0635 (10)
C22	0.3608 (4)	0.5051 (3)	0.2014 (3)	0.0711 (11)
H1	0.08030	0.56490	0.69840	0.0360*
H2A	0.14190	0.65930	0.45740	0.0420*
H2B	0.15850	0.54040	0.53240	0.0420*
H4A	−0.08390	1.07380	0.56260	0.0420*
H4B	−0.15270	1.09870	0.67040	0.0420*
H7A	−0.07660	0.58760	0.85830	0.0440*
H7B	−0.11540	0.72020	0.91240	0.0440*
H8A	0.19370	0.52470	0.87420	0.0900*
H8B	0.11190	0.55680	0.98440	0.0900*
H8C	0.16290	0.66240	0.91750	0.0900*
H10	−0.38980	0.94420	0.79300	0.0470*
H11	−0.54860	1.09470	0.90760	0.0540*
H13	−0.17430	1.15500	0.98320	0.0510*
H14	−0.01510	1.00070	0.87230	0.0440*
H17	0.34430	0.01180	0.49200	0.0400*
H19	0.22660	0.00150	0.79220	0.0420*
H21A	0.50960	0.59740	0.40700	0.0950*
H21B	0.60320	0.48700	0.33030	0.0950*
H21C	0.45620	0.47980	0.39650	0.0950*
H22A	0.31540	0.45640	0.25000	0.1070*
H22B	0.46660	0.44520	0.18000	0.1070*
H22C	0.29450	0.54070	0.14160	0.1070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0862 (5)	0.0593 (4)	0.0643 (5)	−0.0131 (4)	0.0263 (4)	−0.0387 (4)
N1	0.0397 (9)	0.0192 (7)	0.0270 (10)	−0.0090 (7)	0.0051 (7)	−0.0015 (6)
N2	0.0502 (11)	0.0208 (7)	0.0285 (10)	−0.0087 (7)	0.0104 (8)	−0.0048 (7)
N3	0.0299 (8)	0.0224 (7)	0.0233 (9)	−0.0067 (6)	0.0040 (7)	−0.0031 (6)
N4	0.0496 (10)	0.0220 (7)	0.0266 (10)	−0.0091 (7)	0.0105 (8)	−0.0032 (7)
C2	0.0281 (10)	0.0228 (8)	0.0303 (11)	−0.0077 (7)	0.0029 (8)	−0.0035 (7)
C4	0.0300 (10)	0.0240 (8)	0.0241 (11)	−0.0102 (7)	0.0016 (8)	−0.0032 (7)
C5	0.0324 (10)	0.0249 (9)	0.0235 (11)	−0.0101 (8)	0.0015 (8)	−0.0046 (7)
C6	0.0330 (10)	0.0253 (9)	0.0265 (11)	−0.0107 (8)	0.0039 (8)	−0.0031 (7)
C7	0.0497 (13)	0.0284 (9)	0.0297 (12)	−0.0155 (9)	0.0090 (10)	−0.0015 (8)
C8	0.0822 (19)	0.0650 (16)	0.0357 (16)	−0.0341 (15)	−0.0157 (13)	0.0131 (13)
C9	0.0349 (11)	0.0243 (8)	0.0249 (11)	−0.0106 (8)	0.0038 (8)	−0.0017 (7)
C10	0.0374 (12)	0.0421 (11)	0.0371 (14)	−0.0129 (9)	0.0030 (10)	−0.0161 (10)
C11	0.0397 (13)	0.0511 (13)	0.0377 (15)	−0.0108 (10)	0.0100 (10)	−0.0149 (11)
C12	0.0544 (14)	0.0316 (10)	0.0298 (13)	−0.0081 (10)	0.0118 (10)	−0.0106 (9)
C13	0.0580 (15)	0.0374 (11)	0.0342 (14)	−0.0190 (11)	−0.0003 (11)	−0.0127 (10)
C14	0.0414 (12)	0.0386 (11)	0.0320 (13)	−0.0177 (9)	0.0016 (9)	−0.0101 (9)
O1	0.0713 (11)	0.0246 (7)	0.0401 (10)	−0.0197 (7)	0.0068 (8)	−0.0060 (6)
O2	0.0928 (14)	0.0307 (8)	0.0512 (12)	−0.0215 (9)	0.0281 (10)	−0.0079 (7)
O3	0.0490 (9)	0.0442 (8)	0.0407 (10)	−0.0218 (7)	0.0068 (7)	−0.0147 (7)
O4	0.0465 (10)	0.0315 (8)	0.0734 (14)	−0.0150 (7)	−0.0003 (9)	−0.0181 (8)
O5	0.0688 (12)	0.0322 (8)	0.0680 (14)	−0.0223 (8)	−0.0087 (10)	0.0084 (8)
O6	0.1165 (18)	0.0539 (11)	0.0464 (13)	−0.0319 (11)	0.0168 (12)	−0.0003 (9)
O7	0.211 (3)	0.0403 (11)	0.0693 (17)	−0.0356 (15)	0.0555 (19)	−0.0150 (10)
N5	0.0358 (9)	0.0314 (9)	0.0408 (12)	−0.0143 (7)	0.0063 (8)	−0.0102 (8)
N6	0.0368 (10)	0.0256 (8)	0.0675 (16)	−0.0117 (8)	−0.0077 (10)	−0.0056 (9)
N7	0.0626 (13)	0.0329 (9)	0.0430 (13)	−0.0222 (9)	0.0081 (10)	−0.0065 (9)
C15	0.0313 (10)	0.0242 (9)	0.0396 (13)	−0.0102 (8)	−0.0005 (9)	−0.0050 (8)
C16	0.0272 (10)	0.0266 (9)	0.0389 (13)	−0.0100 (8)	0.0005 (8)	−0.0060 (8)
C17	0.0235 (10)	0.0286 (9)	0.0461 (14)	−0.0078 (8)	0.0002 (9)	−0.0099 (9)
C18	0.0287 (10)	0.0213 (9)	0.0566 (16)	−0.0112 (8)	−0.0009 (9)	−0.0054 (9)
C19	0.0334 (11)	0.0282 (9)	0.0449 (14)	−0.0138 (8)	−0.0015 (9)	0.0012 (9)
C20	0.0343 (11)	0.0278 (9)	0.0376 (13)	−0.0114 (8)	0.0027 (9)	−0.0057 (8)
S1	0.0656 (4)	0.0337 (3)	0.0400 (4)	−0.0121 (3)	0.0110 (3)	−0.0026 (2)
O8	0.0625 (10)	0.0289 (7)	0.0378 (10)	−0.0029 (7)	0.0094 (8)	−0.0074 (6)
C21	0.0658 (18)	0.0564 (15)	0.066 (2)	−0.0222 (14)	−0.0113 (15)	−0.0009 (14)
C22	0.077 (2)	0.0597 (16)	0.059 (2)	−0.0026 (14)	−0.0029 (15)	−0.0355 (15)

Geometric parameters (Å, º)

Cl1—C12	1.739 (2)	C9—C14	1.376 (3)
S1—O8	1.4997 (19)	C9—C10	1.384 (4)
S1—C21	1.781 (3)	C10—C11	1.391 (3)
S1—C22	1.773 (3)	C11—C12	1.366 (4)
O1—C15	1.238 (2)	C12—C13	1.368 (4)
O2—N5	1.217 (2)	C13—C14	1.386 (3)
O3—N5	1.229 (2)	C7—H7A	0.9900
O4—N6	1.220 (3)	C7—H7B	0.9900
O5—N6	1.238 (3)	C8—H8C	0.9800
O6—N7	1.194 (3)	C8—H8B	0.9800
O7—N7	1.208 (3)	C8—H8A	0.9800
N1—C6	1.377 (3)	C10—H10	0.9500
N1—C2	1.360 (3)	C11—H11	0.9500
N2—C2	1.322 (3)	C13—H13	0.9500
N3—C2	1.334 (2)	C14—H14	0.9500
N3—C4	1.344 (2)	C15—C16	1.464 (3)
N4—C4	1.326 (2)	C15—C20	1.452 (3)
N1—H1	0.8800	C16—C17	1.376 (3)
N2—H2B	0.8800	C17—C18	1.380 (3)
N2—H2A	0.8800	C18—C19	1.373 (3)
N4—H4A	0.8800	C19—C20	1.376 (3)
N4—H4B	0.8800	C17—H17	0.9500
N5—C16	1.452 (3)	C19—H19	0.9500
N6—C18	1.458 (3)	C21—H21A	0.9800
N7—C20	1.455 (3)	C21—H21B	0.9800
C4—C5	1.433 (3)	C21—H21C	0.9800
C5—C6	1.367 (3)	C22—H22A	0.9800
C5—C9	1.489 (3)	C22—H22B	0.9800
C6—C7	1.495 (3)	C22—H22C	0.9800
C7—C8	1.526 (5)
Cl1···C22^i	3.496 (4)	C4···C17^v	3.542 (3)
Cl1···H22B^i	2.9000	C4···N6^ix	3.362 (3)
S1···C13^ii	3.573 (2)	C4···O5^ix	3.299 (3)
S1···C12^ii	3.557 (2)	C5···O3^v	3.157 (3)
S1···H4B^ii	3.0100	C6···O3^v	3.241 (3)
O1···O7	2.621 (3)	C7···O7	3.138 (3)
O1···N1	2.827 (2)	C8···O7	3.264 (4)
O1···C2	3.269 (2)	C11···C11^x	3.373 (4)
O1···N7	2.875 (3)	C12···S1^ii	3.557 (2)
O1···O2	2.656 (3)	C13···S1^ii	3.573 (2)
O1···C21^iii	3.417 (4)	C14···N4	3.338 (3)
O1···N2	2.827 (2)	C16···C2^v	3.464 (3)
O1···N5	2.917 (2)	C16···N3^v	3.366 (3)
O2···O1	2.656 (3)	C17···C4^v	3.542 (3)
O2···N2	2.862 (2)	C17···C17^iv	3.509 (3)
O2···O4^iv	3.167 (3)	C17···N3^v	3.268 (3)
O3···C4^v	3.255 (3)	C18···O3^iv	3.235 (3)
O3···C18^iv	3.235 (3)	C21···O1^iii	3.417 (4)
O3···N6^iv	3.017 (3)	C22···Cl1^xi	3.496 (4)
O3···C2^v	3.402 (3)	C2···H4A^ii	3.0800
O3···C6^v	3.241 (3)	C4···H4A^ii	2.9900
O3···O4^iv	2.977 (3)	C8···H1	2.9800
O3···C5^v	3.157 (3)	C9···H7B	2.6000
O4···O2^iv	3.167 (3)	C9···H4B	2.5000
O4···O3^iv	2.977 (3)	C10···H7B	2.9800
O4···N3^vi	3.164 (3)	C11···H11^x	3.0300
O4···C2^vi	3.417 (3)	C14···H4B	2.7900
O4···N5^iv	2.964 (3)	C15···H2B	3.0700
O5···C4^vi	3.299 (3)	C17···H17^iv	3.0400
O7···C7	3.138 (3)	C19···H14^vi	3.0900
O7···C8	3.264 (4)	H1···O1	2.0500
O7···O1	2.621 (3)	H1···H7A	2.4600
O8···N2	2.953 (3)	H1···C8	2.9800
O8···N4^ii	2.765 (2)	H1···H8A	2.5300
O1···H1	2.0500	H1···O7	2.6900
O1···H2B	2.0400	H1···H2B	2.2700
O2···H2B	2.1800	H2A···O8	2.0800
O2···H21C	2.6000	H2B···O1	2.0400
O2···H22A	2.6900	H2B···C15	3.0700
O3···H17	2.3000	H2B···H1	2.2700
O3···H10^v	2.7200	H2B···O2	2.1800
O4···H21C^iv	2.8100	H4A···C2^ii	3.0800
O4···H17	2.4100	H4A···O8^ii	2.9100
O5···H22B^iv	2.8200	H4A···N3^ii	2.1200
O5···H19	2.4200	H4A···C4^ii	2.9900
O6···H11^vii	2.7400	H4A···H4A^ii	2.4500
O6···H14^vi	2.8700	H4B···S1^ii	3.0100
O6···H7B^viii	2.8100	H4B···C9	2.5000
O6···H19	2.3600	H4B···C14	2.7900
O7···H7A	2.3800	H4B···O8^ii	2.0500
O7···H8A	2.7700	H7A···H1	2.4600
O7···H1	2.6900	H7A···H8B^viii	2.5700
O8···H2A	2.0800	H7A···O7	2.3800
O8···H4B^ii	2.0500	H7B···C10	2.9800
O8···H4A^ii	2.9100	H7B···O6^viii	2.8100
N1···O1	2.827 (2)	H7B···C9	2.6000
N2···O8	2.953 (3)	H8A···H1	2.5300
N2···O1	2.827 (2)	H8A···N1	2.8500
N2···O2	2.862 (2)	H8A···O7	2.7700
N3···N4^ii	2.996 (2)	H8B···H7A^viii	2.5700
N3···O4^ix	3.164 (3)	H8C···H13^xii	2.5700
N3···N6^ix	3.159 (3)	H10···O3^v	2.7200
N3···C16^v	3.366 (3)	H11···C11^x	3.0300
N3···C17^v	3.268 (3)	H11···O6^xiii	2.7400
N4···N3^ii	2.996 (2)	H13···H8C^xii	2.5700
N4···O8^ii	2.765 (2)	H14···H19^ix	2.4300
N4···C14	3.338 (3)	H14···O6^ix	2.8700
N5···C2^v	3.208 (3)	H14···C19^ix	3.0900
N5···O4^iv	2.964 (3)	H17···C17^iv	3.0400
N5···O1	2.917 (2)	H17···O4	2.4100
N6···C4^vi	3.362 (3)	H17···O3	2.3000
N6···O3^iv	3.017 (3)	H19···O5	2.4200
N6···N3^vi	3.159 (3)	H19···O6	2.3600
N7···O1	2.875 (3)	H19···H14^vi	2.4300
N1···H8A	2.8500	H21C···O2	2.6000
N3···H4A^ii	2.1200	H21C···H22A	2.5000
C2···O1	3.269 (2)	H21C···O4^iv	2.8100
C2···O4^ix	3.417 (3)	H22A···O2	2.6900
C2···N5^v	3.208 (3)	H22A···H21C	2.5000
C2···C16^v	3.464 (3)	H22B···Cl1^xi	2.9000
C2···O3^v	3.402 (3)	H22B···O5^iv	2.8200
C4···O3^v	3.255 (3)
C21—S1—C22	97.39 (16)	C8—C7—H7A	109.00
O8—S1—C21	105.84 (13)	C6—C7—H7A	109.00
O8—S1—C22	105.76 (15)	H7A—C7—H7B	108.00
C2—N1—C6	121.51 (15)	C7—C8—H8B	109.00
C2—N3—C4	117.92 (17)	H8B—C8—H8C	109.00
C6—N1—H1	119.00	C7—C8—H8A	110.00
C2—N1—H1	119.00	H8A—C8—H8B	109.00
C2—N2—H2A	120.00	H8A—C8—H8C	109.00
C2—N2—H2B	120.00	C7—C8—H8C	109.00
H2A—N2—H2B	120.00	C11—C10—H10	120.00
C4—N4—H4A	120.00	C9—C10—H10	120.00
H4A—N4—H4B	120.00	C12—C11—H11	120.00
C4—N4—H4B	120.00	C10—C11—H11	120.00
O2—N5—O3	121.25 (19)	C14—C13—H13	120.00
O2—N5—C16	120.36 (18)	C12—C13—H13	120.00
O3—N5—C16	118.39 (16)	C13—C14—H14	119.00
O4—N6—O5	124.15 (18)	C9—C14—H14	119.00
O5—N6—C18	117.1 (2)	O1—C15—C16	124.6 (2)
O4—N6—C18	118.7 (2)	O1—C15—C20	123.8 (2)
O6—N7—C20	120.10 (18)	C16—C15—C20	111.65 (16)
O7—N7—C20	119.0 (2)	C15—C16—C17	123.7 (2)
O6—N7—O7	120.6 (2)	N5—C16—C15	120.63 (16)
N1—C2—N2	118.34 (16)	N5—C16—C17	115.61 (19)
N2—C2—N3	119.92 (18)	C16—C17—C18	119.6 (2)
N1—C2—N3	121.75 (17)	N6—C18—C17	118.6 (2)
N3—C4—N4	116.45 (18)	N6—C18—C19	120.0 (2)
N4—C4—C5	120.62 (17)	C17—C18—C19	121.24 (18)
N3—C4—C5	122.93 (16)	C18—C19—C20	119.7 (2)
C4—C5—C6	116.83 (17)	C15—C20—C19	124.1 (2)
C6—C5—C9	123.21 (18)	N7—C20—C15	119.84 (17)
C4—C5—C9	119.91 (16)	N7—C20—C19	116.05 (19)
N1—C6—C5	118.88 (18)	C16—C17—H17	120.00
N1—C6—C7	116.49 (16)	C18—C17—H17	120.00
C5—C6—C7	124.56 (18)	C18—C19—H19	120.00
C6—C7—C8	110.9 (2)	C20—C19—H19	120.00
C10—C9—C14	118.6 (2)	S1—C21—H21A	109.00
C5—C9—C14	122.01 (19)	S1—C21—H21B	109.00
C5—C9—C10	119.26 (18)	S1—C21—H21C	110.00
C9—C10—C11	120.6 (2)	H21A—C21—H21B	109.00
C10—C11—C12	119.2 (3)	H21A—C21—H21C	110.00
Cl1—C12—C11	119.0 (2)	H21B—C21—H21C	109.00
C11—C12—C13	121.3 (2)	S1—C22—H22A	110.00
Cl1—C12—C13	119.70 (19)	S1—C22—H22B	109.00
C12—C13—C14	119.1 (2)	S1—C22—H22C	109.00
C9—C14—C13	121.2 (3)	H22A—C22—H22B	109.00
C8—C7—H7B	109.00	H22A—C22—H22C	109.00
C6—C7—H7B	109.00	H22B—C22—H22C	109.00
C6—N1—C2—N2	−175.86 (19)	C6—C5—C9—C10	−81.3 (3)
C6—N1—C2—N3	3.8 (3)	C6—C5—C9—C14	102.8 (2)
C2—N1—C6—C5	0.0 (3)	C5—C6—C7—C8	−105.3 (2)
C2—N1—C6—C7	−177.1 (2)	N1—C6—C7—C8	71.6 (3)
C4—N3—C2—N1	−4.0 (3)	C5—C9—C10—C11	−177.27 (19)
C4—N3—C2—N2	175.69 (19)	C14—C9—C10—C11	−1.2 (3)
C2—N3—C4—N4	−178.82 (19)	C5—C9—C14—C13	176.23 (19)
C2—N3—C4—C5	0.5 (3)	C10—C9—C14—C13	0.3 (3)
O2—N5—C16—C17	179.3 (2)	C9—C10—C11—C12	2.0 (3)
O3—N5—C16—C15	−177.14 (19)	C10—C11—C12—C13	−1.8 (3)
O2—N5—C16—C15	2.6 (3)	C10—C11—C12—Cl1	178.19 (18)
O3—N5—C16—C17	−0.4 (3)	C11—C12—C13—C14	0.9 (3)
O5—N6—C18—C19	−0.6 (3)	Cl1—C12—C13—C14	−179.10 (17)
O5—N6—C18—C17	−177.5 (2)	C12—C13—C14—C9	−0.1 (3)
O4—N6—C18—C17	1.5 (3)	O1—C15—C16—N5	−5.2 (3)
O4—N6—C18—C19	178.4 (2)	O1—C15—C16—C17	178.4 (2)
O6—N7—C20—C15	−170.8 (2)	C20—C15—C16—N5	176.53 (18)
O6—N7—C20—C19	10.9 (3)	C20—C15—C16—C17	0.1 (3)
O7—N7—C20—C15	15.2 (4)	O1—C15—C20—N7	5.4 (3)
O7—N7—C20—C19	−163.2 (3)	O1—C15—C20—C19	−176.4 (2)
N4—C4—C5—C9	5.2 (3)	C16—C15—C20—N7	−176.31 (18)
N3—C4—C5—C6	3.0 (3)	C16—C15—C20—C19	1.9 (3)
N3—C4—C5—C9	−174.16 (19)	N5—C16—C17—C18	−178.48 (19)
N4—C4—C5—C6	−177.6 (2)	C15—C16—C17—C18	−1.9 (3)
C9—C5—C6—N1	173.90 (19)	C16—C17—C18—N6	178.69 (19)
C9—C5—C6—C7	−9.3 (3)	C16—C17—C18—C19	1.8 (3)
C4—C5—C9—C10	95.7 (2)	N6—C18—C19—C20	−176.72 (19)
C4—C5—C6—C7	173.6 (2)	C17—C18—C19—C20	0.1 (3)
C4—C5—C6—N1	−3.2 (3)	C18—C19—C20—N7	176.19 (19)
C4—C5—C9—C14	−80.2 (3)	C18—C19—C20—C15	−2.1 (3)

Symmetry codes: (i) x−1, y+1, z+1; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1; (vi) x, y−1, z; (vii) x+1, y−1, z; (viii) −x, −y+1, −z+2; (ix) x, y+1, z; (x) −x−1, −y+2, −z+2; (xi) x+1, y−1, z−1; (xii) −x, −y+2, −z+2; (xiii) x−1, y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	2.05	2.827 (2)	147
N2—H2A···O8	0.88	2.08	2.953 (3)	169
N2—H2B···O1	0.88	2.04	2.827 (2)	148
N2—H2B···O2	0.88	2.18	2.862 (2)	134
N4—H4A···N3^ii	0.88	2.12	2.996 (2)	170
N4—H4B···O8^ii	0.88	2.05	2.765 (2)	137
C7—H7A···O7	0.99	2.38	3.138 (3)	133
C17—H17···O3	0.95	2.30	2.636 (3)	100

Symmetry code: (ii) −x, −y+2, −z+1.