A triclinic polymorph of 4-cyano-pyridinium hydrogen chloranilate.

THE ASYMMETRIC UNIT OF THE TRICLINIC POLYMORPH OF THE TITLE COMPOUND (SYSTEMATIC NAME: 4-cyano-pyridinium 2,5-dichloro-4-hy-droxy-3,6-dioxocyclo-hexa-1,4-dien-1-olate), C(6)H(5)N(2) (+)·C(6)HCl(2)O(4) (-), consists of two crystallographically independent cation-anion units, in each of which the cation and the anion are linked by an N-H⋯O hydrogen bond. In the units, the dihedral angles between the cation and anion rings are 78.43 (11) and 80.71 (11)°. In the crystal, each unit independently forms a chain through N-H⋯O and O-H⋯N hydrogen bonds; one chain runs along the c axis while the other runs along [011]. Weak C-H⋯O, C-H⋯N and C-H⋯Cl inter-actions are observed between the chains.

Related literature

For the monoclinic polymorph, see: Tomura & Yamashita (2008 ▶); Gotoh et al. (2008 ▶). For hydrogen-bonding patterns in chloranilic acid–organic base (1/1) systems, see: Ishida & Kashino (2002 ▶). For 35Cl nuclear quadrupole resonance studies on proton transfer in chloranilic acid–organic base systems, see: Nihei et al. (2000 ▶).

Experimental

Crystal data

C6H5N2 +·C6HCl2O4 −

M = 313.10

Triclinic,

a = 9.3918 (7) Å

b = 10.6652 (7) Å

c = 13.9135 (8) Å

α = 111.8033 (18)°

β = 106.258 (3)°

γ = 90.416 (3)°

V = 1232.50 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.54 mm−1

T = 180 K

0.36 × 0.31 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.866, T max = 0.953

21354 measured reflections

7135 independent reflections

4934 reflections with I > 2σ(I)

R int = 0.108

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.164

S = 0.99

7135 reflections

377 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.89 e Å−3

Δρmin = −0.83 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037221/lh5521sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037221/lh5521Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037221/lh5521Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H5N2+·C6HCl2O4−	Z = 4
Mr = 313.10	F(000) = 632.00
Triclinic, P1	Dx = 1.687 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 9.3918 (7) Å	Cell parameters from 17217 reflections
b = 10.6652 (7) Å	θ = 3.1–30.1°
c = 13.9135 (8) Å	µ = 0.54 mm−1
α = 111.8033 (18)°	T = 180 K
β = 106.258 (3)°	Platelet, brown
γ = 90.416 (3)°	0.36 × 0.31 × 0.09 mm
V = 1232.50 (14) Å3

Rigaku R-AXIS RAPID II diffractometer	4934 reflections with I > 2σ(I)
ω scans	Rint = 0.108
Absorption correction: numerical (NUMABS; Higashi, 1999)	θmax = 30.0°
Tmin = 0.866, Tmax = 0.953	h = −13→13
21354 measured reflections	k = −14→14
7135 independent reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0762P)2] where P = (Fo2 + 2Fc2)/3
7135 reflections	(Δ/σ)max = 0.001
377 parameters	Δρmax = 0.89 e Å−3
0 restraints	Δρmin = −0.83 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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.

	x	y	z	Uiso*/Ueq
Cl1	0.29193 (7)	0.49544 (6)	−0.10659 (5)	0.04057 (16)
Cl2	0.68163 (7)	1.06889 (5)	0.18401 (5)	0.03666 (15)
Cl3	0.21149 (7)	0.59716 (6)	0.62343 (5)	0.03851 (16)
Cl4	−0.16421 (7)	0.85552 (7)	0.30375 (5)	0.04279 (17)
O1	0.51735 (19)	0.64141 (17)	−0.15370 (13)	0.0396 (4)
O2	0.32328 (17)	0.66708 (16)	0.12870 (12)	0.0346 (3)
O3	0.48242 (18)	0.91360 (17)	0.24401 (13)	0.0363 (4)
O4	0.67459 (19)	0.88479 (17)	−0.03878 (14)	0.0343 (4)
O5	−0.01092 (19)	0.79448 (17)	0.65480 (13)	0.0384 (4)
O6	0.19311 (18)	0.52007 (16)	0.38448 (13)	0.0364 (4)
O7	0.04975 (18)	0.65162 (17)	0.26162 (13)	0.0370 (4)
O8	−0.16121 (19)	0.90831 (17)	0.53085 (14)	0.0376 (4)
N1	0.4187 (2)	0.7224 (2)	0.33632 (16)	0.0344 (4)
N2	0.6554 (2)	0.7841 (2)	0.74522 (17)	0.0424 (5)
N3	0.0861 (2)	0.3707 (2)	0.16703 (16)	0.0341 (4)
N4	−0.1526 (2)	0.0443 (2)	−0.24595 (17)	0.0413 (5)
C1	0.4981 (2)	0.7009 (2)	−0.06484 (17)	0.0298 (4)
C2	0.3989 (2)	0.6506 (2)	−0.02287 (17)	0.0302 (4)
C3	0.3974 (2)	0.7129 (2)	0.08301 (17)	0.0296 (4)
C4	0.4895 (2)	0.8540 (2)	0.15269 (17)	0.0289 (4)
C5	0.5819 (2)	0.9100 (2)	0.10598 (17)	0.0296 (4)
C6	0.5880 (2)	0.8389 (2)	0.00544 (17)	0.0292 (4)
C7	0.0119 (2)	0.7548 (2)	0.56596 (17)	0.0301 (4)
C8	0.1100 (2)	0.6605 (2)	0.53026 (18)	0.0306 (4)
C9	0.1187 (2)	0.6129 (2)	0.42538 (17)	0.0292 (4)
C10	0.0303 (2)	0.6811 (2)	0.35009 (17)	0.0305 (4)
C11	−0.0679 (2)	0.7803 (2)	0.38836 (18)	0.0319 (4)
C12	−0.0762 (2)	0.8166 (2)	0.48929 (18)	0.0301 (4)
C13	0.3814 (3)	0.8248 (2)	0.41276 (19)	0.0354 (5)
H13	0.3173	0.8851	0.3923	0.042*
C14	0.4348 (3)	0.8434 (2)	0.52031 (19)	0.0338 (5)
H14	0.4081	0.9150	0.5750	0.041*
C15	0.5302 (3)	0.7526 (2)	0.54595 (18)	0.0321 (4)
C16	0.5662 (3)	0.6461 (2)	0.46590 (19)	0.0378 (5)
H16	0.6298	0.5841	0.4839	0.045*
C17	0.5075 (3)	0.6327 (2)	0.3596 (2)	0.0381 (5)
H17	0.5296	0.5603	0.3030	0.046*
C18	0.5972 (3)	0.7707 (2)	0.65759 (19)	0.0357 (5)
C19	0.1208 (3)	0.4009 (2)	0.09031 (19)	0.0359 (5)
H19	0.1878	0.4798	0.1103	0.043*
C20	0.0589 (3)	0.3172 (2)	−0.01748 (18)	0.0342 (5)
H20	0.0824	0.3372	−0.0728	0.041*
C21	−0.0390 (2)	0.2024 (2)	−0.04369 (17)	0.0303 (4)
C22	−0.0737 (3)	0.1742 (2)	0.03736 (19)	0.0355 (5)
H22	−0.1409	0.0965	0.0200	0.043*
C23	−0.0083 (3)	0.2619 (2)	0.14348 (19)	0.0363 (5)
H23	−0.0304	0.2448	0.2004	0.044*
C24	−0.1034 (3)	0.1137 (2)	−0.15641 (18)	0.0340 (5)
H1	0.384 (3)	0.713 (3)	0.263 (3)	0.063 (9)*
H3	0.121 (3)	0.432 (3)	0.236 (3)	0.056 (9)*
H4	0.665 (4)	0.833 (4)	−0.100 (3)	0.068 (11)*
H8	−0.140 (4)	0.918 (4)	0.603 (4)	0.097 (13)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0498 (4)	0.0352 (3)	0.0327 (3)	−0.0051 (3)	0.0117 (3)	0.0097 (2)
Cl2	0.0453 (3)	0.0310 (3)	0.0314 (3)	−0.0010 (2)	0.0092 (2)	0.0116 (2)
Cl3	0.0490 (3)	0.0387 (3)	0.0311 (3)	0.0160 (3)	0.0107 (3)	0.0180 (2)
Cl4	0.0500 (4)	0.0509 (4)	0.0361 (3)	0.0186 (3)	0.0126 (3)	0.0265 (3)
O1	0.0532 (10)	0.0367 (9)	0.0316 (8)	0.0031 (8)	0.0210 (8)	0.0102 (7)
O2	0.0398 (9)	0.0382 (8)	0.0290 (8)	0.0011 (7)	0.0142 (7)	0.0139 (7)
O3	0.0433 (9)	0.0379 (8)	0.0292 (8)	0.0064 (7)	0.0169 (7)	0.0104 (7)
O4	0.0431 (9)	0.0355 (8)	0.0282 (8)	0.0033 (7)	0.0172 (7)	0.0119 (7)
O5	0.0533 (10)	0.0417 (9)	0.0305 (8)	0.0177 (8)	0.0226 (8)	0.0181 (7)
O6	0.0396 (9)	0.0368 (8)	0.0322 (8)	0.0112 (7)	0.0112 (7)	0.0123 (7)
O7	0.0490 (10)	0.0388 (9)	0.0289 (8)	0.0111 (7)	0.0183 (7)	0.0145 (7)
O8	0.0428 (9)	0.0399 (9)	0.0348 (9)	0.0173 (7)	0.0156 (8)	0.0168 (8)
N1	0.0418 (11)	0.0349 (9)	0.0277 (9)	0.0021 (8)	0.0118 (8)	0.0127 (8)
N2	0.0492 (12)	0.0501 (12)	0.0346 (10)	0.0079 (10)	0.0168 (10)	0.0210 (10)
N3	0.0393 (10)	0.0356 (10)	0.0286 (9)	0.0110 (8)	0.0114 (9)	0.0127 (9)
N4	0.0495 (12)	0.0425 (11)	0.0331 (10)	0.0096 (9)	0.0152 (10)	0.0139 (9)
C1	0.0364 (11)	0.0292 (10)	0.0274 (10)	0.0085 (9)	0.0120 (9)	0.0132 (9)
C2	0.0349 (11)	0.0279 (10)	0.0267 (10)	0.0035 (9)	0.0089 (9)	0.0099 (9)
C3	0.0318 (11)	0.0303 (10)	0.0281 (10)	0.0046 (8)	0.0080 (9)	0.0135 (9)
C4	0.0317 (10)	0.0310 (10)	0.0277 (10)	0.0094 (9)	0.0111 (9)	0.0138 (9)
C5	0.0326 (11)	0.0284 (10)	0.0286 (10)	0.0042 (8)	0.0088 (9)	0.0123 (9)
C6	0.0316 (10)	0.0303 (10)	0.0288 (10)	0.0059 (8)	0.0093 (9)	0.0148 (9)
C7	0.0332 (11)	0.0297 (10)	0.0286 (10)	0.0038 (9)	0.0080 (9)	0.0138 (9)
C8	0.0345 (11)	0.0304 (10)	0.0289 (10)	0.0070 (9)	0.0073 (9)	0.0153 (9)
C9	0.0299 (10)	0.0291 (10)	0.0288 (10)	0.0049 (8)	0.0084 (9)	0.0118 (9)
C10	0.0331 (11)	0.0312 (10)	0.0278 (10)	0.0026 (9)	0.0081 (9)	0.0129 (9)
C11	0.0346 (11)	0.0355 (11)	0.0291 (10)	0.0064 (9)	0.0078 (9)	0.0177 (9)
C12	0.0315 (11)	0.0293 (10)	0.0315 (11)	0.0068 (9)	0.0113 (9)	0.0127 (9)
C13	0.0405 (12)	0.0333 (11)	0.0360 (12)	0.0060 (10)	0.0126 (10)	0.0166 (10)
C14	0.0408 (12)	0.0313 (10)	0.0313 (10)	0.0069 (9)	0.0149 (10)	0.0114 (9)
C15	0.0367 (11)	0.0345 (11)	0.0284 (10)	0.0023 (9)	0.0116 (9)	0.0147 (9)
C16	0.0463 (13)	0.0356 (11)	0.0362 (12)	0.0108 (10)	0.0175 (11)	0.0155 (10)
C17	0.0472 (13)	0.0363 (12)	0.0346 (11)	0.0093 (10)	0.0193 (11)	0.0128 (10)
C18	0.0407 (12)	0.0390 (12)	0.0338 (11)	0.0078 (10)	0.0166 (10)	0.0173 (10)
C19	0.0383 (12)	0.0352 (11)	0.0371 (12)	0.0039 (9)	0.0138 (10)	0.0158 (10)
C20	0.0409 (12)	0.0360 (11)	0.0313 (11)	0.0061 (10)	0.0159 (10)	0.0156 (10)
C21	0.0354 (11)	0.0322 (10)	0.0276 (10)	0.0093 (9)	0.0133 (9)	0.0136 (9)
C22	0.0435 (13)	0.0348 (11)	0.0346 (11)	0.0047 (10)	0.0162 (10)	0.0172 (10)
C23	0.0465 (13)	0.0400 (12)	0.0311 (11)	0.0113 (10)	0.0170 (10)	0.0194 (10)
C24	0.0373 (12)	0.0378 (11)	0.0317 (11)	0.0083 (10)	0.0140 (10)	0.0160 (10)

Cl1—C2	1.730 (2)	C4—C5	1.460 (3)
Cl2—C5	1.722 (2)	C5—C6	1.339 (3)
Cl3—C8	1.736 (2)	C7—C8	1.416 (3)
Cl4—C11	1.721 (2)	C7—C12	1.514 (3)
O1—C1	1.228 (3)	C8—C9	1.382 (3)
O2—C3	1.265 (2)	C9—C10	1.551 (3)
O3—C4	1.213 (2)	C10—C11	1.457 (3)
O4—C6	1.333 (2)	C11—C12	1.336 (3)
O4—H4	0.80 (4)	C13—C14	1.374 (3)
O5—C7	1.231 (2)	C13—H13	0.9500
O6—C9	1.267 (3)	C14—C15	1.399 (3)
O7—C10	1.219 (2)	C14—H14	0.9500
O8—C12	1.334 (3)	C15—C16	1.386 (3)
O8—H8	0.93 (4)	C15—C18	1.440 (3)
N1—C13	1.341 (3)	C16—C17	1.377 (3)
N1—C17	1.344 (3)	C16—H16	0.9500
N1—H1	0.95 (3)	C17—H17	0.9500
N2—C18	1.141 (3)	C19—C20	1.376 (3)
N3—C23	1.334 (3)	C19—H19	0.9500
N3—C19	1.341 (3)	C20—C21	1.393 (3)
N3—H3	0.90 (3)	C20—H20	0.9500
N4—C24	1.141 (3)	C21—C22	1.387 (3)
C1—C2	1.424 (3)	C21—C24	1.442 (3)
C1—C6	1.512 (3)	C22—C23	1.375 (3)
C2—C3	1.377 (3)	C22—H22	0.9500
C3—C4	1.543 (3)	C23—H23	0.9500
C6—O4—H4	111 (2)	C12—C11—C10	120.14 (19)
C12—O8—H8	105 (2)	C12—C11—Cl4	121.12 (18)
C13—N1—C17	122.6 (2)	C10—C11—Cl4	118.65 (16)
C13—N1—H1	120 (2)	O8—C12—C11	123.68 (19)
C17—N1—H1	118 (2)	O8—C12—C7	114.58 (18)
C23—N3—C19	122.6 (2)	C11—C12—C7	121.7 (2)
C23—N3—H3	119.4 (19)	N1—C13—C14	120.7 (2)
C19—N3—H3	118 (2)	N1—C13—H13	119.6
O1—C1—C2	125.5 (2)	C14—C13—H13	119.6
O1—C1—C6	116.86 (18)	C13—C14—C15	117.2 (2)
C2—C1—C6	117.66 (19)	C13—C14—H14	121.4
C3—C2—C1	122.6 (2)	C15—C14—H14	121.4
C3—C2—Cl1	120.10 (16)	C16—C15—C14	121.4 (2)
C1—C2—Cl1	116.92 (17)	C16—C15—C18	118.3 (2)
O2—C3—C2	126.0 (2)	C14—C15—C18	120.2 (2)
O2—C3—C4	115.97 (19)	C17—C16—C15	118.3 (2)
C2—C3—C4	117.96 (18)	C17—C16—H16	120.9
O3—C4—C5	122.7 (2)	C15—C16—H16	120.9
O3—C4—C3	118.70 (18)	N1—C17—C16	119.8 (2)
C5—C4—C3	118.59 (18)	N1—C17—H17	120.1
C6—C5—C4	120.3 (2)	C16—C17—H17	120.1
C6—C5—Cl2	121.68 (16)	N2—C18—C15	177.4 (3)
C4—C5—Cl2	117.99 (16)	N3—C19—C20	119.8 (2)
O4—C6—C5	122.1 (2)	N3—C19—H19	120.1
O4—C6—C1	115.73 (19)	C20—C19—H19	120.1
C5—C6—C1	122.17 (18)	C19—C20—C21	118.5 (2)
O5—C7—C8	127.07 (19)	C19—C20—H20	120.7
O5—C7—C12	114.44 (19)	C21—C20—H20	120.7
C8—C7—C12	118.49 (19)	C22—C21—C20	120.5 (2)
C9—C8—C7	122.90 (18)	C22—C21—C24	120.7 (2)
C9—C8—Cl3	120.81 (16)	C20—C21—C24	118.83 (19)
C7—C8—Cl3	116.14 (16)	C23—C22—C21	118.2 (2)
O6—C9—C8	126.72 (19)	C23—C22—H22	120.9
O6—C9—C10	116.38 (18)	C21—C22—H22	120.9
C8—C9—C10	116.90 (18)	N3—C23—C22	120.4 (2)
O7—C10—C11	122.69 (19)	N3—C23—H23	119.8
O7—C10—C9	117.86 (19)	C22—C23—H23	119.8
C11—C10—C9	119.41 (18)	N4—C24—C21	178.9 (3)
O1—C1—C2—C3	170.6 (2)	O6—C9—C10—O7	−7.3 (3)
C6—C1—C2—C3	−9.2 (3)	C8—C9—C10—O7	171.9 (2)
O1—C1—C2—Cl1	−2.5 (3)	O6—C9—C10—C11	174.71 (19)
C6—C1—C2—Cl1	177.63 (15)	C8—C9—C10—C11	−6.1 (3)
C1—C2—C3—O2	−172.6 (2)	O7—C10—C11—C12	−174.8 (2)
Cl1—C2—C3—O2	0.3 (3)	C9—C10—C11—C12	3.1 (3)
C1—C2—C3—C4	9.6 (3)	O7—C10—C11—Cl4	1.7 (3)
Cl1—C2—C3—C4	−177.44 (15)	C9—C10—C11—Cl4	179.63 (15)
O2—C3—C4—O3	−2.2 (3)	C10—C11—C12—O8	178.7 (2)
C2—C3—C4—O3	175.76 (19)	Cl4—C11—C12—O8	2.3 (3)
O2—C3—C4—C5	177.69 (18)	C10—C11—C12—C7	−1.4 (3)
C2—C3—C4—C5	−4.4 (3)	Cl4—C11—C12—C7	−177.88 (16)
O3—C4—C5—C6	178.8 (2)	O5—C7—C12—O8	2.3 (3)
C3—C4—C5—C6	−1.1 (3)	C8—C7—C12—O8	−177.45 (19)
O3—C4—C5—Cl2	−1.2 (3)	O5—C7—C12—C11	−177.6 (2)
C3—C4—C5—Cl2	178.92 (14)	C8—C7—C12—C11	2.7 (3)
C4—C5—C6—O4	−177.88 (19)	C17—N1—C13—C14	0.8 (3)
Cl2—C5—C6—O4	2.1 (3)	N1—C13—C14—C15	0.7 (3)
C4—C5—C6—C1	1.6 (3)	C13—C14—C15—C16	−1.6 (3)
Cl2—C5—C6—C1	−178.48 (15)	C13—C14—C15—C18	176.4 (2)
O1—C1—C6—O4	2.9 (3)	C14—C15—C16—C17	1.0 (3)
C2—C1—C6—O4	−177.21 (18)	C18—C15—C16—C17	−177.1 (2)
O1—C1—C6—C5	−176.6 (2)	C13—N1—C17—C16	−1.4 (3)
C2—C1—C6—C5	3.3 (3)	C15—C16—C17—N1	0.5 (3)
O5—C7—C8—C9	174.2 (2)	C23—N3—C19—C20	−0.5 (3)
C12—C7—C8—C9	−6.1 (3)	N3—C19—C20—C21	0.0 (3)
O5—C7—C8—Cl3	−1.5 (3)	C19—C20—C21—C22	0.5 (3)
C12—C7—C8—Cl3	178.26 (15)	C19—C20—C21—C24	−179.5 (2)
C7—C8—C9—O6	−173.2 (2)	C20—C21—C22—C23	−0.4 (3)
Cl3—C8—C9—O6	2.2 (3)	C24—C21—C22—C23	179.6 (2)
C7—C8—C9—C10	7.6 (3)	C19—N3—C23—C22	0.6 (3)
Cl3—C8—C9—C10	−176.91 (15)	C21—C22—C23—N3	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.95 (4)	1.67 (4)	2.602 (2)	170 (3)
N3—H3···O6	0.90 (4)	1.84 (4)	2.719 (3)	166 (3)
O4—H4···N2i	0.80 (4)	1.99 (4)	2.741 (3)	155 (4)
O8—H8···N4ii	0.93 (5)	2.07 (5)	2.875 (3)	144 (4)
C13—H13···N4iii	0.95	2.55	3.407 (3)	150
C14—H14···O3iv	0.95	2.42	3.209 (3)	141
C16—H16···Cl3v	0.95	2.71	3.431 (3)	133
C17—H17···O1vi	0.95	2.30	3.194 (3)	157
C19—H19···O2	0.95	2.25	3.192 (3)	170
C20—H20···Cl1	0.95	2.83	3.626 (3)	142
C23—H23···O5vii	0.95	2.14	3.040 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.95 (4)	1.67 (4)	2.602 (2)	170 (3)
N3—H3⋯O6	0.90 (4)	1.84 (4)	2.719 (3)	166 (3)
O4—H4⋯N2i	0.80 (4)	1.99 (4)	2.741 (3)	155 (4)
O8—H8⋯N4ii	0.93 (5)	2.07 (5)	2.875 (3)	144 (4)
C13—H13⋯N4iii	0.95	2.55	3.407 (3)	150
C14—H14⋯O3iv	0.95	2.42	3.209 (3)	141
C16—H16⋯Cl3v	0.95	2.71	3.431 (3)	133
C17—H17⋯O1vi	0.95	2.30	3.194 (3)	157
C19—H19⋯O2	0.95	2.25	3.192 (3)	170
C20—H20⋯Cl1	0.95	2.83	3.626 (3)	142
C23—H23⋯O5vii	0.95	2.14	3.040 (3)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .