1:2 Complexes of chloranilic acid with pyrazole and imidazole, and the aceto­nitrile solvate of a 1:1 complex with imidazole

2,5-Di­chloro-3,6-di­hydroxy-1,4-benzo­quinone (chloranilic acid) forms X—H...Y (X, Y = N or O) and C—H...Cl hydrogen bonds with pyrazole and imidazole to afford bis­(pyrazolium) di­chloro­anilate and bis­(imidazolium) di­chloro­anilate, (I) and (II), both 2C₃H₅N₂⁺·C₆Cl₂O₄²⁻, and imidazolium chloro­anilate aceto­nitrile solvate, C₃H₅N₂⁺·­C₆HCl₂O₄⁻·C₂H₃N, (III). Their crystal structures demonstrate three novel supramolecular architectures based on supramolecular synthons to build a ladder, (I), a two-dimensional network, (II), and a flat ribbon, (III).

Computing details

For all compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN for Windows; software used to prepare material for publication: TEXSAN for Windows.

(I)

Crystal data

2C3H5N2^+·C6Cl2O4^2^−	F(000) = 352
Mr = 345.14	Dx = 1.660 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.043 (3) Å	Cell parameters from 25 reflections
b = 5.459 (3) Å	θ = 10.9–12.5°
c = 15.740 (4) Å	µ = 0.49 mm^−1
β = 92.73 (2)°	T = 292 K
V = 690.3 (4) Å^3	Prismatic, brown
Z = 2	0.45 × 0.40 × 0.30 mm

Data collection

Rigaku AFC5R diffractometer	1299 reflections with I > 2.00σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.018
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
ω–2θ scans	h = −1→10
Absorption correction: ψ scans (North et al., 1968)	k = 0→7
Tmin = 0.77, Tmax = 0.86	l = −20→20
2127 measured reflections	3 standard reflections every 97 reflections
1591 independent reflections	intensity decay: none

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.050	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo) + 0.00019|Fo|^2]
wR(F^2) = 0.076	(Δ/σ)max = 0.01
S = 1.43	Δρmax = 0.29 e Å^−3
1590 reflections	Δρmin = −0.32 e Å^−3
121 parameters	Extinction correction: Zachariasen (1967), equ(3) Acta Cryst.(1968) A24, p213.
0 restraints	Extinction coefficient: 3.23 (8)×10^-5

Special details

Experimental. The scan width was (1.52 + 0.30tanθ)° with an ω scan speed of 6° per minute (up to 3 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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

	x	y	z	Uiso*/Ueq
Cl	0.77568 (5)	0.41654 (7)	0.51585 (2)	0.03446 (11)
O1	0.53162 (13)	0.3192 (2)	0.37115 (6)	0.0310 (3)
O2	0.69125 (14)	0.0368 (2)	0.64484 (7)	0.0359 (3)
N1	0.29495 (16)	0.3987 (3)	0.24777 (8)	0.0315 (4)
N2	0.20487 (16)	0.6026 (3)	0.25451 (8)	0.0307 (3)
C1	0.52293 (17)	0.1763 (3)	0.43255 (9)	0.0238 (3)
C2	0.62439 (18)	0.1886 (3)	0.50745 (9)	0.0256 (4)
C3	0.60819 (17)	0.0294 (3)	0.57544 (9)	0.0244 (3)
C4	0.0982 (2)	0.6161 (3)	0.18695 (10)	0.0340 (4)
C5	0.1198 (2)	0.4145 (3)	0.13732 (10)	0.0351 (4)
C6	0.2448 (2)	0.2790 (3)	0.17734 (10)	0.0344 (4)
H1	0.366 (3)	0.352 (5)	0.2888 (14)	0.082 (8)*
H2	0.230 (2)	0.719 (4)	0.2945 (12)	0.047 (5)*
H3	0.022 (2)	0.749 (4)	0.1809 (11)	0.044 (5)*
H4	0.063 (2)	0.365 (3)	0.0869 (11)	0.044 (5)*
H5	0.297 (2)	0.122 (4)	0.1620 (11)	0.046 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0318 (2)	0.0331 (2)	0.0377 (2)	−0.01018 (16)	−0.00681 (15)	0.00358 (17)
O1	0.0309 (6)	0.0330 (6)	0.0287 (5)	−0.0044 (5)	−0.0033 (4)	0.0066 (5)
O2	0.0430 (6)	0.0332 (6)	0.0301 (5)	−0.0086 (5)	−0.0138 (5)	0.0034 (5)
N1	0.0308 (7)	0.0326 (8)	0.0306 (7)	0.0010 (6)	−0.0044 (5)	0.0032 (6)
N2	0.0328 (7)	0.0303 (7)	0.0287 (6)	−0.0014 (6)	−0.0020 (5)	−0.0037 (6)
C1	0.0228 (7)	0.0233 (7)	0.0252 (7)	0.0022 (6)	0.0002 (5)	−0.0005 (6)
C2	0.0234 (7)	0.0250 (7)	0.0281 (7)	−0.0047 (6)	−0.0019 (6)	−0.0014 (6)
C3	0.0239 (7)	0.0245 (7)	0.0244 (7)	0.0013 (6)	−0.0032 (5)	−0.0031 (6)
C4	0.0301 (8)	0.0371 (9)	0.0343 (8)	0.0042 (7)	−0.0031 (6)	0.0031 (7)
C5	0.0332 (8)	0.0431 (10)	0.0283 (8)	−0.0058 (8)	−0.0050 (6)	−0.0036 (7)
C6	0.0372 (9)	0.0326 (9)	0.0335 (8)	−0.0006 (7)	0.0014 (7)	−0.0038 (7)

Geometric parameters (Å, º)

Cl—C2	1.7409 (18)	C1—C2	1.403 (2)
O1—C1	1.247 (2)	C1—C3^i	1.541 (2)
O2—C3	1.2537 (19)	C2—C3	1.390 (2)
N1—N2	1.335 (2)	C4—C5	1.366 (3)
N1—C6	1.333 (2)	C4—H3	0.95 (2)
N1—H1	0.88 (3)	C5—C6	1.376 (3)
N2—C4	1.336 (2)	C5—H4	0.93 (2)
N2—H2	0.91 (2)	C6—H5	0.99 (2)
O1···N1	2.689 (2)	O2···N2^iv	2.638 (2)
O1···N2^ii	3.194 (2)	O2···N1^i	2.916 (2)
O1···C6^iii	3.201 (3)
N2—N1—C6	109.31 (16)	O2—C3—C1^i	115.40 (15)
N2—N1—H1	121.3 (19)	O2—C3—C2	125.80 (16)
C6—N1—H1	129.0 (19)	C1^i—C3—C2	118.80 (14)
N1—N2—C4	108.25 (15)	N2—C4—C5	108.44 (17)
N1—N2—H2	122.2 (14)	N2—C4—H3	120.5 (13)
C4—N2—H2	128.7 (14)	C5—C4—H3	131.0 (13)
O1—C1—C2	124.72 (16)	C4—C5—C6	106.34 (17)
O1—C1—C3^i	117.13 (14)	C4—C5—H4	130.4 (13)
C2—C1—C3^i	118.15 (15)	C6—C5—H4	123.3 (13)
Cl—C2—C1	118.33 (13)	N1—C6—C5	107.65 (18)
Cl—C2—C3	118.65 (13)	N1—C6—H5	120.8 (12)
C1—C2—C3	123.02 (16)	C5—C6—H5	131.6 (12)
Cl—C2—C1—O1	−0.8 (3)	O2—C3—C1^i—C2^i	177.59 (15)
Cl—C2—C1—C3^i	178.65 (12)	O2—C3—C2—C1	−177.45 (17)
Cl—C2—C3—O2	1.8 (3)	N1—N2—C4—C5	1.0 (2)
Cl—C2—C3—C1^i	−178.64 (12)	N1—C6—C5—C4	−0.4 (2)
O1—C1—C2—C3	178.38 (17)	N2—N1—C6—C5	1.0 (2)
O1—C1—C3^i—O2^i	1.9 (2)	N2—C4—C5—C6	−0.4 (2)
O1—C1—C3^i—C2^i	−178.43 (16)	C4—N2—N1—C6	−1.2 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88 (3)	1.82 (3)	2.689 (2)	168 (3)
N1—H1···O2^i	0.88 (3)	2.42 (3)	2.916 (2)	116 (2)
N2—H2···O2^iv	0.91 (2)	1.74 (2)	2.638 (2)	167 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1.

(II)

Crystal data

2C3H5N2^+·C6Cl2O4^2^−	F(000) = 352
Mr = 345.14	Dx = 1.615 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.547 (2) Å	Cell parameters from 25 reflections
b = 8.1565 (15) Å	θ = 10.7–12.2°
c = 11.750 (4) Å	µ = 0.48 mm^−1
β = 101.10 (3)°	T = 298 K
V = 709.7 (3) Å^3	Prismatic, brown
Z = 2	0.50 × 0.30 × 0.20 mm

Data collection

Rigaku AFC5R diffractometer	1172 reflections with I > 2.00σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.023
Graphite monochromator	θmax = 27.5°, θmin = 1.8°
ω–2θ scans	h = −1→9
Absorption correction: ψ scans (North et al., 1968)	k = 0→10
Tmin = 0.85, Tmax = 0.91	l = −15→15
2141 measured reflections	3 standard reflections every 97 reflections
1634 independent reflections	intensity decay: none

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.051	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo) + 0.00011|Fo|^2]
wR(F^2) = 0.073	(Δ/σ)max = 0.01
S = 1.35	Δρmax = 0.32 e Å^−3
1634 reflections	Δρmin = −0.36 e Å^−3
121 parameters	Extinction correction: Zachariasen (1967), equ(3) Acta Cryst.(1968) A24, p213.
0 restraints	Extinction coefficient: 1.39 (5)×10^-5

Special details

Experimental. The scan width was (1.47 + 0.30tanθ)° with an ω scan speed of 6° per minute (up to 3 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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

	x	y	z	Uiso*/Ueq
Cl	0.94157 (7)	0.34025 (8)	0.24999 (4)	0.05631 (18)
O1	0.68582 (15)	0.34976 (17)	0.41228 (10)	0.0411 (4)
O2	1.27089 (15)	0.51528 (16)	0.37886 (10)	0.0360 (4)
N1	0.4538 (2)	0.2328 (2)	0.55218 (14)	0.0401 (5)
N2	0.3374 (2)	0.0908 (2)	0.67238 (14)	0.0416 (5)
C1	0.8326 (2)	0.4192 (2)	0.44819 (14)	0.0287 (5)
C2	0.9745 (2)	0.4311 (2)	0.38626 (14)	0.0323 (5)
C3	1.1390 (2)	0.5050 (2)	0.42959 (14)	0.0277 (4)
C4	0.4605 (3)	0.2013 (3)	0.66271 (17)	0.0431 (6)
C5	0.2497 (3)	0.0493 (3)	0.56364 (19)	0.0457 (6)
C6	0.3223 (3)	0.1378 (3)	0.48878 (17)	0.0439 (6)
H1	0.525 (3)	0.299 (3)	0.523 (2)	0.085 (8)*
H2	0.535 (3)	0.247 (3)	0.7266 (17)	0.056 (6)*
H3	0.309 (3)	0.047 (3)	0.745 (2)	0.100 (9)*
H4	0.162 (3)	−0.030 (3)	0.5561 (17)	0.060 (7)*
H5	0.299 (2)	0.136 (2)	0.4066 (16)	0.044 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0474 (3)	0.0859 (5)	0.0394 (3)	−0.0218 (3)	0.0177 (2)	−0.0301 (3)
O1	0.0332 (7)	0.0568 (9)	0.0344 (7)	−0.0147 (6)	0.0093 (5)	−0.0071 (7)
O2	0.0302 (6)	0.0464 (8)	0.0346 (7)	−0.0021 (6)	0.0144 (5)	−0.0044 (6)
N1	0.0336 (9)	0.0472 (11)	0.0420 (9)	−0.0010 (8)	0.0133 (7)	0.0121 (8)
N2	0.0383 (9)	0.0504 (11)	0.0401 (9)	0.0022 (8)	0.0171 (7)	0.0126 (9)
C1	0.0287 (9)	0.0304 (10)	0.0275 (9)	−0.0011 (8)	0.0066 (7)	−0.0003 (8)
C2	0.0326 (9)	0.0410 (11)	0.0248 (8)	−0.0036 (8)	0.0092 (7)	−0.0082 (8)
C3	0.0290 (9)	0.0270 (9)	0.0278 (9)	0.0030 (7)	0.0071 (7)	0.0006 (7)
C4	0.0330 (10)	0.0564 (15)	0.0394 (11)	0.0012 (10)	0.0054 (9)	0.0023 (10)
C5	0.0378 (11)	0.0439 (13)	0.0553 (14)	−0.0051 (10)	0.0090 (10)	0.0033 (11)
C6	0.0453 (11)	0.0522 (14)	0.0332 (11)	0.0037 (10)	0.0046 (9)	0.0023 (10)

Geometric parameters (Å, º)

Cl—C2	1.738 (2)	N2—H3	0.99 (3)
O1—C1	1.243 (2)	C1—C2	1.410 (3)
O2—C3	1.258 (2)	C1—C3^i	1.540 (3)
N1—C4	1.315 (3)	C2—C3	1.385 (3)
N1—C6	1.362 (3)	C4—H2	0.92 (2)
N1—H1	0.88 (3)	C5—C6	1.335 (3)
N2—C4	1.315 (3)	C5—H4	0.92 (2)
N2—C5	1.364 (3)	C6—H5	0.95 (2)
O1···N1	2.790 (2)	O2···N1^i	2.924 (3)
O1···C4^ii	3.121 (3)	O2···C4^i	3.174 (3)
O1···C5^iii	3.295 (3)	O2···N1^v	3.206 (3)
O2···N2^iv	2.712 (2)
C4—N1—C6	108.3 (2)	O2—C3—C1^i	115.75 (17)
C4—N1—H1	126.8 (19)	O2—C3—C2	126.14 (19)
C6—N1—H1	124.8 (19)	C1^i—C3—C2	118.11 (16)
C4—N2—C5	108.3 (2)	N1—C4—N2	109.0 (2)
C4—N2—H3	126.7 (18)	N1—C4—H2	128.6 (15)
C5—N2—H3	125.0 (18)	N2—C4—H2	122.4 (15)
O1—C1—C2	124.90 (19)	N2—C5—C6	107.2 (2)
O1—C1—C3^i	117.02 (16)	N2—C5—H4	118.5 (15)
C2—C1—C3^i	118.07 (17)	C6—C5—H4	134.3 (15)
Cl—C2—C1	117.26 (16)	N1—C6—C5	107.2 (2)
Cl—C2—C3	118.88 (15)	N1—C6—H5	122.4 (13)
C1—C2—C3	123.81 (18)	C5—C6—H5	130.3 (14)
Cl—C2—C1—O1	−0.5 (3)	O2—C3—C1^i—C2^i	−178.38 (19)
Cl—C2—C1—C3^i	178.44 (14)	O2—C3—C2—C1	178.2 (2)
Cl—C2—C3—O2	0.8 (3)	N1—C4—N2—C5	0.5 (3)
Cl—C2—C3—C1^i	−178.40 (15)	N1—C6—C5—N2	−0.0 (3)
O1—C1—C2—C3	−178.0 (2)	N2—C4—N1—C6	−0.5 (3)
O1—C1—C3^i—O2^i	−2.6 (3)	C4—N1—C6—C5	0.3 (3)
O1—C1—C3^i—C2^i	178.14 (19)	C4—N2—C5—C6	−0.3 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88 (3)	1.98 (3)	2.790 (2)	152 (3)
N1—H1···O2^i	0.88 (3)	2.30 (3)	2.924 (2)	127 (2)
N2—H3···O2^vi	0.99 (3)	1.72 (3)	2.712 (2)	175 (3)

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

(III)

Crystal data

C3H5N2^+·C6HCl2O4^−·C2H3N	Z = 2
Mr = 318.12	F(000) = 324
Triclinic, P1	Dx = 1.573 Mg m^−3
a = 9.3895 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.628 (2) Å	Cell parameters from 25 reflections
c = 8.214 (2) Å	θ = 10.7–12.3°
α = 95.86 (2)°	µ = 0.50 mm^−1
β = 99.82 (2)°	T = 297 K
γ = 111.156 (16)°	Prismatic, dark brown
V = 671.4 (3) Å^3	0.50 × 0.30 × 0.25 mm

Data collection

Rigaku AFC5R diffractometer	2048 reflections with I > 2.00σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.023
Graphite monochromator	θmax = 27.5°, θmin = 2.3°
ω–2θ scans	h = 0→12
Absorption correction: ψ scans (North et al., 1968)	k = −12→11
Tmin = 0.84, Tmax = 0.88	l = −10→10
3283 measured reflections	3 standard reflections every 97 reflections
3093 independent reflections	intensity decay: none

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.052	All H-atom parameters refined
wR(F^2) = 0.063	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo) + 0.00006|Fo|^2]
S = 1.37	(Δ/σ)max = 0.01
3093 reflections	Δρmax = 0.41 e Å^−3
217 parameters	Δρmin = −0.45 e Å^−3

Special details

Experimental. The scan width was (1.52 + 0.30tanθ)° with an ω scan speed of 6° per minute (up to 3 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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

	x	y	z	Uiso*/Ueq
Cl1	0.09437 (6)	−0.23493 (5)	−0.21826 (6)	0.04240 (15)
Cl2	0.02691 (6)	0.39836 (5)	−0.16726 (7)	0.04850 (16)
O1	0.27177 (14)	0.04715 (14)	0.03616 (16)	0.0416 (4)
O2	−0.14564 (14)	−0.15415 (13)	−0.44194 (16)	0.0417 (4)
O3	−0.18037 (15)	0.11123 (14)	−0.40303 (16)	0.0419 (4)
O4	0.25179 (16)	0.31178 (15)	0.05331 (17)	0.0436 (4)
N1	0.4168 (2)	−0.1310 (2)	0.1539 (2)	0.0443 (5)
N2	0.6001 (2)	−0.1492 (2)	0.3339 (2)	0.0471 (6)
N3	0.5128 (3)	0.3372 (3)	0.3019 (3)	0.0835 (8)
C1	0.1657 (2)	0.05204 (19)	−0.0759 (2)	0.0294 (5)
C2	0.0658 (2)	−0.06625 (18)	−0.2055 (2)	0.0297 (5)
C3	−0.0532 (2)	−0.05324 (19)	−0.3239 (2)	0.0300 (5)
C4	−0.0720 (2)	0.10064 (19)	−0.3072 (2)	0.0295 (5)
C5	0.0403 (2)	0.22383 (18)	−0.1788 (2)	0.0318 (5)
C6	0.1497 (2)	0.20174 (19)	−0.0685 (2)	0.0309 (5)
C7	0.5365 (3)	−0.0563 (3)	0.2829 (3)	0.0477 (7)
C8	0.4059 (3)	−0.2758 (3)	0.1236 (3)	0.0524 (7)
C9	0.5196 (3)	−0.2880 (3)	0.2345 (3)	0.0532 (7)
C10	0.6242 (3)	0.3943 (2)	0.3986 (3)	0.0513 (7)
C11	0.7691 (4)	0.4704 (4)	0.5226 (4)	0.0678 (9)
H1	0.316 (3)	0.278 (3)	0.109 (3)	0.086 (8)*
H2	0.361 (3)	−0.077 (3)	0.104 (3)	0.089 (8)*
H3	0.571 (2)	0.052 (2)	0.332 (3)	0.070 (7)*
H4	0.691 (3)	−0.121 (3)	0.421 (3)	0.087 (8)*
H5	0.546 (3)	−0.377 (3)	0.252 (3)	0.081 (8)*
H6	0.334 (3)	−0.347 (3)	0.045 (3)	0.083 (8)*
H7	0.804 (4)	0.403 (4)	0.559 (5)	0.178 (13)*
H8	0.749 (3)	0.500 (3)	0.609 (4)	0.105 (11)*
H9	0.826 (5)	0.551 (4)	0.480 (5)	0.194 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0469 (3)	0.0315 (3)	0.0473 (3)	0.0216 (2)	−0.0044 (2)	0.0018 (2)
Cl2	0.0606 (4)	0.0344 (3)	0.0501 (3)	0.0284 (3)	−0.0075 (3)	0.0013 (2)
O1	0.0375 (8)	0.0413 (8)	0.0409 (8)	0.0205 (7)	−0.0127 (6)	0.0021 (6)
O2	0.0428 (8)	0.0351 (7)	0.0382 (8)	0.0167 (7)	−0.0115 (6)	−0.0043 (6)
O3	0.0414 (8)	0.0448 (8)	0.0389 (8)	0.0248 (7)	−0.0087 (6)	0.0034 (6)
O4	0.0416 (8)	0.0358 (8)	0.0422 (9)	0.0157 (7)	−0.0133 (7)	−0.0062 (6)
N1	0.0370 (10)	0.0551 (11)	0.0469 (11)	0.0263 (9)	0.0020 (8)	0.0157 (9)
N2	0.0333 (10)	0.0632 (12)	0.0411 (11)	0.0175 (10)	−0.0021 (8)	0.0150 (10)
N3	0.0683 (15)	0.0765 (15)	0.0774 (16)	0.0204 (13)	−0.0291 (12)	−0.0050 (13)
C1	0.0264 (9)	0.0330 (10)	0.0302 (10)	0.0145 (8)	0.0027 (8)	0.0067 (8)
C2	0.0327 (10)	0.0258 (9)	0.0321 (11)	0.0165 (8)	0.0005 (8)	0.0034 (8)
C3	0.0306 (10)	0.0316 (10)	0.0284 (10)	0.0146 (9)	0.0030 (8)	0.0041 (8)
C4	0.0312 (10)	0.0340 (10)	0.0258 (10)	0.0168 (8)	0.0031 (8)	0.0063 (8)
C5	0.0391 (11)	0.0262 (9)	0.0313 (11)	0.0178 (9)	0.0001 (9)	0.0032 (8)
C6	0.0303 (10)	0.0296 (10)	0.0288 (10)	0.0112 (8)	0.0002 (8)	−0.0001 (8)
C7	0.0488 (13)	0.0400 (12)	0.0511 (14)	0.0138 (11)	0.0131 (11)	0.0029 (11)
C8	0.0438 (14)	0.0483 (14)	0.0534 (15)	0.0136 (11)	−0.0045 (11)	−0.0009 (12)
C9	0.0527 (14)	0.0469 (14)	0.0649 (16)	0.0268 (12)	0.0051 (12)	0.0163 (12)
C10	0.0503 (14)	0.0433 (13)	0.0519 (14)	0.0187 (11)	−0.0096 (11)	0.0051 (11)
C11	0.0563 (17)	0.072 (2)	0.0525 (18)	0.0142 (15)	−0.0165 (14)	0.0012 (15)

Geometric parameters (Å, º)

Cl1—C2	1.7350 (19)	C1—C2	1.397 (3)
Cl2—C5	1.724 (2)	C1—C6	1.498 (3)
O1—C1	1.253 (2)	C2—C3	1.402 (3)
O2—C3	1.245 (2)	C3—C4	1.549 (3)
O3—C4	1.218 (2)	C4—C5	1.446 (3)
O4—C6	1.329 (2)	C5—C6	1.342 (3)
O4—H1	0.86 (3)	C7—H3	0.99 (2)
N1—C7	1.326 (3)	C8—C9	1.328 (3)
N1—C8	1.354 (3)	C8—H6	0.88 (3)
N1—H2	0.94 (3)	C9—H5	0.99 (3)
N2—C7	1.307 (3)	C10—C11	1.443 (4)
N2—C9	1.365 (3)	C11—H7	0.88 (4)
N2—H4	0.95 (3)	C11—H8	0.81 (3)
N3—C10	1.114 (3)	C11—H9	0.91 (4)
O1···N1	2.703 (2)	O2···C3^iii	3.239 (3)
O1···N3	3.193 (3)	O3···N2^ii	2.974 (3)
O1···C4^i	3.263 (3)	O3···C7^ii	3.168 (3)
O2···N2^ii	2.773 (2)	O4···N3	2.827 (3)
O2···C4^iii	3.095 (3)	N2···C1^iv	3.273 (3)
C6—O4—H1	109.3 (19)	C4—C5—C6	120.76 (18)
C7—N1—C8	108.0 (2)	O4—C6—C1	115.73 (17)
C7—N1—H2	117.7 (17)	O4—C6—C5	122.08 (19)
C8—N1—H2	134.3 (17)	C1—C6—C5	122.19 (19)
C7—N2—C9	108.5 (2)	N1—C7—N2	108.7 (2)
C7—N2—H4	124.4 (17)	N1—C7—H3	124.9 (15)
C9—N2—H4	127.0 (17)	N2—C7—H3	126.3 (15)
O1—C1—C2	126.34 (19)	N1—C8—C9	107.8 (2)
O1—C1—C6	115.36 (18)	N1—C8—H6	124.3 (19)
C2—C1—C6	118.29 (17)	C9—C8—H6	127.9 (19)
Cl1—C2—C1	117.32 (15)	N2—C9—C8	107.0 (2)
Cl1—C2—C3	119.69 (15)	N2—C9—H5	122.6 (15)
C1—C2—C3	122.99 (18)	C8—C9—H5	130.3 (15)
O2—C3—C2	125.99 (18)	N3—C10—C11	179.1 (3)
O2—C3—C4	116.69 (17)	C10—C11—H7	110 (3)
C2—C3—C4	117.33 (18)	C10—C11—H8	108 (3)
O3—C4—C3	118.16 (18)	C10—C11—H9	106 (3)
O3—C4—C5	123.64 (18)	H7—C11—H8	99 (3)
C3—C4—C5	118.19 (17)	H7—C11—H9	125 (4)
Cl2—C5—C4	118.45 (15)	H8—C11—H9	110 (4)
Cl2—C5—C6	120.77 (16)
Cl1—C2—C1—O1	−2.3 (3)	O3—C4—C5—C6	174.7 (2)
Cl1—C2—C1—C6	176.31 (17)	O4—C6—C1—C2	−177.4 (2)
Cl1—C2—C3—O2	0.5 (3)	O4—C6—C5—C4	−178.3 (2)
Cl1—C2—C3—C4	−179.34 (15)	N1—C7—N2—C9	0.3 (3)
Cl2—C5—C4—O3	−3.5 (3)	N1—C8—C9—N2	0.3 (3)
Cl2—C5—C4—C3	176.38 (16)	N2—C7—N1—C8	−0.1 (3)
Cl2—C5—C6—O4	−0.1 (3)	C1—C2—C3—C4	0.1 (3)
Cl2—C5—C6—C1	−179.41 (17)	C1—C6—C5—C4	2.4 (4)
O1—C1—C2—C3	178.2 (2)	C2—C1—C6—C5	2.0 (3)
O1—C1—C6—O4	1.4 (3)	C2—C3—C4—C5	4.2 (3)
O1—C1—C6—C5	−179.2 (2)	C3—C2—C1—C6	−3.1 (3)
O2—C3—C2—C1	179.9 (2)	C3—C4—C5—C6	−5.4 (3)
O2—C3—C4—O3	4.3 (3)	C7—N1—C8—C9	−0.1 (3)
O2—C3—C4—C5	−175.7 (2)	C7—N2—C9—C8	−0.3 (3)
O3—C4—C3—C2	−175.9 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···N3	0.86 (3)	2.08 (3)	2.827 (3)	145 (3)
O4—H1···O1	0.86 (3)	2.11 (3)	2.613 (2)	116 (2)
N1—H2···O1	0.94 (3)	1.78 (3)	2.703 (2)	171 (3)
N2—H4···O2^v	0.95 (3)	1.89 (3)	2.773 (2)	154 (2)
N2—H4···O3^v	0.95 (3)	2.31 (3)	2.974 (3)	127 (2)
C11—H7···Cl2^v	0.88 (4)	2.81 (5)	3.507 (4)	136 (4)

Symmetry code: (v) x+1, y, z+1.