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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).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101000944/de1164sup1.cif
Contains datablocks General, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000944/de1164Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000944/de1164IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000944/de1164IIIsup4.hkl
Contains datablock III

CCDC references: 163938; 163939; 163940

Computing details top

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) top
Crystal data top
2C3H5N2+·C6Cl2O42F(000) = 352
Mr = 345.14Dx = 1.660 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.043 (3) ÅCell parameters from 25 reflections
b = 5.459 (3) Åθ = 10.9–12.5°
c = 15.740 (4) ŵ = 0.49 mm1
β = 92.73 (2)°T = 292 K
V = 690.3 (4) Å3Prismatic, brown
Z = 20.45 × 0.40 × 0.30 mm
Data collection top
Rigaku AFC5R
diffractometer
1299 reflections with I > 2.00σ(I)
Radiation source: Rigaku rotating anodeRint = 0.018
Graphite monochromatorθmax = 27.5°, θmin = 2.5°
ω–2θ scansh = 110
Absorption correction: ψ scans
(North et al., 1968)
k = 07
Tmin = 0.77, Tmax = 0.86l = 2020
2127 measured reflections3 standard reflections every 97 reflections
1591 independent reflections intensity decay: none
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.050Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00019|Fo|2]
wR(F2) = 0.076(Δ/σ)max = 0.01
S = 1.43Δρmax = 0.29 e Å3
1590 reflectionsΔρmin = 0.32 e Å3
121 parametersExtinction correction: Zachariasen (1967), equ(3) Acta Cryst.(1968) A24, p213.
0 restraintsExtinction coefficient: 3.23 (8)×10-5
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl0.77568 (5)0.41654 (7)0.51585 (2)0.03446 (11)
O10.53162 (13)0.3192 (2)0.37115 (6)0.0310 (3)
O20.69125 (14)0.0368 (2)0.64484 (7)0.0359 (3)
N10.29495 (16)0.3987 (3)0.24777 (8)0.0315 (4)
N20.20487 (16)0.6026 (3)0.25451 (8)0.0307 (3)
C10.52293 (17)0.1763 (3)0.43255 (9)0.0238 (3)
C20.62439 (18)0.1886 (3)0.50745 (9)0.0256 (4)
C30.60819 (17)0.0294 (3)0.57544 (9)0.0244 (3)
C40.0982 (2)0.6161 (3)0.18695 (10)0.0340 (4)
C50.1198 (2)0.4145 (3)0.13732 (10)0.0351 (4)
C60.2448 (2)0.2790 (3)0.17734 (10)0.0344 (4)
H10.366 (3)0.352 (5)0.2888 (14)0.082 (8)*
H20.230 (2)0.719 (4)0.2945 (12)0.047 (5)*
H30.022 (2)0.749 (4)0.1809 (11)0.044 (5)*
H40.063 (2)0.365 (3)0.0869 (11)0.044 (5)*
H50.297 (2)0.122 (4)0.1620 (11)0.046 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0318 (2)0.0331 (2)0.0377 (2)0.01018 (16)0.00681 (15)0.00358 (17)
O10.0309 (6)0.0330 (6)0.0287 (5)0.0044 (5)0.0033 (4)0.0066 (5)
O20.0430 (6)0.0332 (6)0.0301 (5)0.0086 (5)0.0138 (5)0.0034 (5)
N10.0308 (7)0.0326 (8)0.0306 (7)0.0010 (6)0.0044 (5)0.0032 (6)
N20.0328 (7)0.0303 (7)0.0287 (6)0.0014 (6)0.0020 (5)0.0037 (6)
C10.0228 (7)0.0233 (7)0.0252 (7)0.0022 (6)0.0002 (5)0.0005 (6)
C20.0234 (7)0.0250 (7)0.0281 (7)0.0047 (6)0.0019 (6)0.0014 (6)
C30.0239 (7)0.0245 (7)0.0244 (7)0.0013 (6)0.0032 (5)0.0031 (6)
C40.0301 (8)0.0371 (9)0.0343 (8)0.0042 (7)0.0031 (6)0.0031 (7)
C50.0332 (8)0.0431 (10)0.0283 (8)0.0058 (8)0.0050 (6)0.0036 (7)
C60.0372 (9)0.0326 (9)0.0335 (8)0.0006 (7)0.0014 (7)0.0038 (7)
Geometric parameters (Å, º) top
Cl—C21.7409 (18)C1—C21.403 (2)
O1—C11.247 (2)C1—C3i1.541 (2)
O2—C31.2537 (19)C2—C31.390 (2)
N1—N21.335 (2)C4—C51.366 (3)
N1—C61.333 (2)C4—H30.95 (2)
N1—H10.88 (3)C5—C61.376 (3)
N2—C41.336 (2)C5—H40.93 (2)
N2—H20.91 (2)C6—H50.99 (2)
O1···N12.689 (2)O2···N2iv2.638 (2)
O1···N2ii3.194 (2)O2···N1i2.916 (2)
O1···C6iii3.201 (3)
N2—N1—C6109.31 (16)O2—C3—C1i115.40 (15)
N2—N1—H1121.3 (19)O2—C3—C2125.80 (16)
C6—N1—H1129.0 (19)C1i—C3—C2118.80 (14)
N1—N2—C4108.25 (15)N2—C4—C5108.44 (17)
N1—N2—H2122.2 (14)N2—C4—H3120.5 (13)
C4—N2—H2128.7 (14)C5—C4—H3131.0 (13)
O1—C1—C2124.72 (16)C4—C5—C6106.34 (17)
O1—C1—C3i117.13 (14)C4—C5—H4130.4 (13)
C2—C1—C3i118.15 (15)C6—C5—H4123.3 (13)
Cl—C2—C1118.33 (13)N1—C6—C5107.65 (18)
Cl—C2—C3118.65 (13)N1—C6—H5120.8 (12)
C1—C2—C3123.02 (16)C5—C6—H5131.6 (12)
Cl—C2—C1—O10.8 (3)O2—C3—C1i—C2i177.59 (15)
Cl—C2—C1—C3i178.65 (12)O2—C3—C2—C1177.45 (17)
Cl—C2—C3—O21.8 (3)N1—N2—C4—C51.0 (2)
Cl—C2—C3—C1i178.64 (12)N1—C6—C5—C40.4 (2)
O1—C1—C2—C3178.38 (17)N2—N1—C6—C51.0 (2)
O1—C1—C3i—O2i1.9 (2)N2—C4—C5—C60.4 (2)
O1—C1—C3i—C2i178.43 (16)C4—N2—N1—C61.2 (2)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.88 (3)1.82 (3)2.689 (2)168 (3)
N1—H1···O2i0.88 (3)2.42 (3)2.916 (2)116 (2)
N2—H2···O2iv0.91 (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) top
Crystal data top
2C3H5N2+·C6Cl2O42F(000) = 352
Mr = 345.14Dx = 1.615 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.547 (2) ÅCell parameters from 25 reflections
b = 8.1565 (15) Åθ = 10.7–12.2°
c = 11.750 (4) ŵ = 0.48 mm1
β = 101.10 (3)°T = 298 K
V = 709.7 (3) Å3Prismatic, brown
Z = 20.50 × 0.30 × 0.20 mm
Data collection top
Rigaku AFC5R
diffractometer
1172 reflections with I > 2.00σ(I)
Radiation source: Rigaku rotating anodeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 1.8°
ω–2θ scansh = 19
Absorption correction: ψ scans
(North et al., 1968)
k = 010
Tmin = 0.85, Tmax = 0.91l = 1515
2141 measured reflections3 standard reflections every 97 reflections
1634 independent reflections intensity decay: none
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.051Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00011|Fo|2]
wR(F2) = 0.073(Δ/σ)max = 0.01
S = 1.35Δρmax = 0.32 e Å3
1634 reflectionsΔρmin = 0.36 e Å3
121 parametersExtinction correction: Zachariasen (1967), equ(3) Acta Cryst.(1968) A24, p213.
0 restraintsExtinction coefficient: 1.39 (5)×10-5
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl0.94157 (7)0.34025 (8)0.24999 (4)0.05631 (18)
O10.68582 (15)0.34976 (17)0.41228 (10)0.0411 (4)
O21.27089 (15)0.51528 (16)0.37886 (10)0.0360 (4)
N10.4538 (2)0.2328 (2)0.55218 (14)0.0401 (5)
N20.3374 (2)0.0908 (2)0.67238 (14)0.0416 (5)
C10.8326 (2)0.4192 (2)0.44819 (14)0.0287 (5)
C20.9745 (2)0.4311 (2)0.38626 (14)0.0323 (5)
C31.1390 (2)0.5050 (2)0.42959 (14)0.0277 (4)
C40.4605 (3)0.2013 (3)0.66271 (17)0.0431 (6)
C50.2497 (3)0.0493 (3)0.56364 (19)0.0457 (6)
C60.3223 (3)0.1378 (3)0.48878 (17)0.0439 (6)
H10.525 (3)0.299 (3)0.523 (2)0.085 (8)*
H20.535 (3)0.247 (3)0.7266 (17)0.056 (6)*
H30.309 (3)0.047 (3)0.745 (2)0.100 (9)*
H40.162 (3)0.030 (3)0.5561 (17)0.060 (7)*
H50.299 (2)0.136 (2)0.4066 (16)0.044 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0474 (3)0.0859 (5)0.0394 (3)0.0218 (3)0.0177 (2)0.0301 (3)
O10.0332 (7)0.0568 (9)0.0344 (7)0.0147 (6)0.0093 (5)0.0071 (7)
O20.0302 (6)0.0464 (8)0.0346 (7)0.0021 (6)0.0144 (5)0.0044 (6)
N10.0336 (9)0.0472 (11)0.0420 (9)0.0010 (8)0.0133 (7)0.0121 (8)
N20.0383 (9)0.0504 (11)0.0401 (9)0.0022 (8)0.0171 (7)0.0126 (9)
C10.0287 (9)0.0304 (10)0.0275 (9)0.0011 (8)0.0066 (7)0.0003 (8)
C20.0326 (9)0.0410 (11)0.0248 (8)0.0036 (8)0.0092 (7)0.0082 (8)
C30.0290 (9)0.0270 (9)0.0278 (9)0.0030 (7)0.0071 (7)0.0006 (7)
C40.0330 (10)0.0564 (15)0.0394 (11)0.0012 (10)0.0054 (9)0.0023 (10)
C50.0378 (11)0.0439 (13)0.0553 (14)0.0051 (10)0.0090 (10)0.0033 (11)
C60.0453 (11)0.0522 (14)0.0332 (11)0.0037 (10)0.0046 (9)0.0023 (10)
Geometric parameters (Å, º) top
Cl—C21.738 (2)N2—H30.99 (3)
O1—C11.243 (2)C1—C21.410 (3)
O2—C31.258 (2)C1—C3i1.540 (3)
N1—C41.315 (3)C2—C31.385 (3)
N1—C61.362 (3)C4—H20.92 (2)
N1—H10.88 (3)C5—C61.335 (3)
N2—C41.315 (3)C5—H40.92 (2)
N2—C51.364 (3)C6—H50.95 (2)
O1···N12.790 (2)O2···N1i2.924 (3)
O1···C4ii3.121 (3)O2···C4i3.174 (3)
O1···C5iii3.295 (3)O2···N1v3.206 (3)
O2···N2iv2.712 (2)
C4—N1—C6108.3 (2)O2—C3—C1i115.75 (17)
C4—N1—H1126.8 (19)O2—C3—C2126.14 (19)
C6—N1—H1124.8 (19)C1i—C3—C2118.11 (16)
C4—N2—C5108.3 (2)N1—C4—N2109.0 (2)
C4—N2—H3126.7 (18)N1—C4—H2128.6 (15)
C5—N2—H3125.0 (18)N2—C4—H2122.4 (15)
O1—C1—C2124.90 (19)N2—C5—C6107.2 (2)
O1—C1—C3i117.02 (16)N2—C5—H4118.5 (15)
C2—C1—C3i118.07 (17)C6—C5—H4134.3 (15)
Cl—C2—C1117.26 (16)N1—C6—C5107.2 (2)
Cl—C2—C3118.88 (15)N1—C6—H5122.4 (13)
C1—C2—C3123.81 (18)C5—C6—H5130.3 (14)
Cl—C2—C1—O10.5 (3)O2—C3—C1i—C2i178.38 (19)
Cl—C2—C1—C3i178.44 (14)O2—C3—C2—C1178.2 (2)
Cl—C2—C3—O20.8 (3)N1—C4—N2—C50.5 (3)
Cl—C2—C3—C1i178.40 (15)N1—C6—C5—N20.0 (3)
O1—C1—C2—C3178.0 (2)N2—C4—N1—C60.5 (3)
O1—C1—C3i—O2i2.6 (3)C4—N1—C6—C50.3 (3)
O1—C1—C3i—C2i178.14 (19)C4—N2—C5—C60.3 (3)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y+1/2, z1/2; (iii) x+1, y, z+1; (iv) x+1, y+1/2, z1/2; (v) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.88 (3)1.98 (3)2.790 (2)152 (3)
N1—H1···O2i0.88 (3)2.30 (3)2.924 (2)127 (2)
N2—H3···O2vi0.99 (3)1.72 (3)2.712 (2)175 (3)
Symmetry codes: (i) x+2, y+1, z+1; (vi) x1, y+1/2, z+1/2.
(III) top
Crystal data top
C3H5N2+·C6HCl2O4·C2H3NZ = 2
Mr = 318.12F(000) = 324
Triclinic, P1Dx = 1.573 Mg m3
a = 9.3895 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.628 (2) ÅCell parameters from 25 reflections
c = 8.214 (2) Åθ = 10.7–12.3°
α = 95.86 (2)°µ = 0.50 mm1
β = 99.82 (2)°T = 297 K
γ = 111.156 (16)°Prismatic, dark brown
V = 671.4 (3) Å30.50 × 0.30 × 0.25 mm
Data collection top
Rigaku AFC5R
diffractometer
2048 reflections with I > 2.00σ(I)
Radiation source: Rigaku rotating anodeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
ω–2θ scansh = 012
Absorption correction: ψ scans
(North et al., 1968)
k = 1211
Tmin = 0.84, Tmax = 0.88l = 1010
3283 measured reflections3 standard reflections every 97 reflections
3093 independent reflections intensity decay: none
Refinement top
Refinement on F20 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.052All H-atom parameters refined
wR(F2) = 0.063Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00006|Fo|2]
S = 1.37(Δ/σ)max = 0.01
3093 reflectionsΔρmax = 0.41 e Å3
217 parametersΔρmin = 0.45 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.09437 (6)0.23493 (5)0.21826 (6)0.04240 (15)
Cl20.02691 (6)0.39836 (5)0.16726 (7)0.04850 (16)
O10.27177 (14)0.04715 (14)0.03616 (16)0.0416 (4)
O20.14564 (14)0.15415 (13)0.44194 (16)0.0417 (4)
O30.18037 (15)0.11123 (14)0.40303 (16)0.0419 (4)
O40.25179 (16)0.31178 (15)0.05331 (17)0.0436 (4)
N10.4168 (2)0.1310 (2)0.1539 (2)0.0443 (5)
N20.6001 (2)0.1492 (2)0.3339 (2)0.0471 (6)
N30.5128 (3)0.3372 (3)0.3019 (3)0.0835 (8)
C10.1657 (2)0.05204 (19)0.0759 (2)0.0294 (5)
C20.0658 (2)0.06625 (18)0.2055 (2)0.0297 (5)
C30.0532 (2)0.05324 (19)0.3239 (2)0.0300 (5)
C40.0720 (2)0.10064 (19)0.3072 (2)0.0295 (5)
C50.0403 (2)0.22383 (18)0.1788 (2)0.0318 (5)
C60.1497 (2)0.20174 (19)0.0685 (2)0.0309 (5)
C70.5365 (3)0.0563 (3)0.2829 (3)0.0477 (7)
C80.4059 (3)0.2758 (3)0.1236 (3)0.0524 (7)
C90.5196 (3)0.2880 (3)0.2345 (3)0.0532 (7)
C100.6242 (3)0.3943 (2)0.3986 (3)0.0513 (7)
C110.7691 (4)0.4704 (4)0.5226 (4)0.0678 (9)
H10.316 (3)0.278 (3)0.109 (3)0.086 (8)*
H20.361 (3)0.077 (3)0.104 (3)0.089 (8)*
H30.571 (2)0.052 (2)0.332 (3)0.070 (7)*
H40.691 (3)0.121 (3)0.421 (3)0.087 (8)*
H50.546 (3)0.377 (3)0.252 (3)0.081 (8)*
H60.334 (3)0.347 (3)0.045 (3)0.083 (8)*
H70.804 (4)0.403 (4)0.559 (5)0.178 (13)*
H80.749 (3)0.500 (3)0.609 (4)0.105 (11)*
H90.826 (5)0.551 (4)0.480 (5)0.194 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0469 (3)0.0315 (3)0.0473 (3)0.0216 (2)0.0044 (2)0.0018 (2)
Cl20.0606 (4)0.0344 (3)0.0501 (3)0.0284 (3)0.0075 (3)0.0013 (2)
O10.0375 (8)0.0413 (8)0.0409 (8)0.0205 (7)0.0127 (6)0.0021 (6)
O20.0428 (8)0.0351 (7)0.0382 (8)0.0167 (7)0.0115 (6)0.0043 (6)
O30.0414 (8)0.0448 (8)0.0389 (8)0.0248 (7)0.0087 (6)0.0034 (6)
O40.0416 (8)0.0358 (8)0.0422 (9)0.0157 (7)0.0133 (7)0.0062 (6)
N10.0370 (10)0.0551 (11)0.0469 (11)0.0263 (9)0.0020 (8)0.0157 (9)
N20.0333 (10)0.0632 (12)0.0411 (11)0.0175 (10)0.0021 (8)0.0150 (10)
N30.0683 (15)0.0765 (15)0.0774 (16)0.0204 (13)0.0291 (12)0.0050 (13)
C10.0264 (9)0.0330 (10)0.0302 (10)0.0145 (8)0.0027 (8)0.0067 (8)
C20.0327 (10)0.0258 (9)0.0321 (11)0.0165 (8)0.0005 (8)0.0034 (8)
C30.0306 (10)0.0316 (10)0.0284 (10)0.0146 (9)0.0030 (8)0.0041 (8)
C40.0312 (10)0.0340 (10)0.0258 (10)0.0168 (8)0.0031 (8)0.0063 (8)
C50.0391 (11)0.0262 (9)0.0313 (11)0.0178 (9)0.0001 (9)0.0032 (8)
C60.0303 (10)0.0296 (10)0.0288 (10)0.0112 (8)0.0002 (8)0.0001 (8)
C70.0488 (13)0.0400 (12)0.0511 (14)0.0138 (11)0.0131 (11)0.0029 (11)
C80.0438 (14)0.0483 (14)0.0534 (15)0.0136 (11)0.0045 (11)0.0009 (12)
C90.0527 (14)0.0469 (14)0.0649 (16)0.0268 (12)0.0051 (12)0.0163 (12)
C100.0503 (14)0.0433 (13)0.0519 (14)0.0187 (11)0.0096 (11)0.0051 (11)
C110.0563 (17)0.072 (2)0.0525 (18)0.0142 (15)0.0165 (14)0.0012 (15)
Geometric parameters (Å, º) top
Cl1—C21.7350 (19)C1—C21.397 (3)
Cl2—C51.724 (2)C1—C61.498 (3)
O1—C11.253 (2)C2—C31.402 (3)
O2—C31.245 (2)C3—C41.549 (3)
O3—C41.218 (2)C4—C51.446 (3)
O4—C61.329 (2)C5—C61.342 (3)
O4—H10.86 (3)C7—H30.99 (2)
N1—C71.326 (3)C8—C91.328 (3)
N1—C81.354 (3)C8—H60.88 (3)
N1—H20.94 (3)C9—H50.99 (3)
N2—C71.307 (3)C10—C111.443 (4)
N2—C91.365 (3)C11—H70.88 (4)
N2—H40.95 (3)C11—H80.81 (3)
N3—C101.114 (3)C11—H90.91 (4)
O1···N12.703 (2)O2···C3iii3.239 (3)
O1···N33.193 (3)O3···N2ii2.974 (3)
O1···C4i3.263 (3)O3···C7ii3.168 (3)
O2···N2ii2.773 (2)O4···N32.827 (3)
O2···C4iii3.095 (3)N2···C1iv3.273 (3)
C6—O4—H1109.3 (19)C4—C5—C6120.76 (18)
C7—N1—C8108.0 (2)O4—C6—C1115.73 (17)
C7—N1—H2117.7 (17)O4—C6—C5122.08 (19)
C8—N1—H2134.3 (17)C1—C6—C5122.19 (19)
C7—N2—C9108.5 (2)N1—C7—N2108.7 (2)
C7—N2—H4124.4 (17)N1—C7—H3124.9 (15)
C9—N2—H4127.0 (17)N2—C7—H3126.3 (15)
O1—C1—C2126.34 (19)N1—C8—C9107.8 (2)
O1—C1—C6115.36 (18)N1—C8—H6124.3 (19)
C2—C1—C6118.29 (17)C9—C8—H6127.9 (19)
Cl1—C2—C1117.32 (15)N2—C9—C8107.0 (2)
Cl1—C2—C3119.69 (15)N2—C9—H5122.6 (15)
C1—C2—C3122.99 (18)C8—C9—H5130.3 (15)
O2—C3—C2125.99 (18)N3—C10—C11179.1 (3)
O2—C3—C4116.69 (17)C10—C11—H7110 (3)
C2—C3—C4117.33 (18)C10—C11—H8108 (3)
O3—C4—C3118.16 (18)C10—C11—H9106 (3)
O3—C4—C5123.64 (18)H7—C11—H899 (3)
C3—C4—C5118.19 (17)H7—C11—H9125 (4)
Cl2—C5—C4118.45 (15)H8—C11—H9110 (4)
Cl2—C5—C6120.77 (16)
Cl1—C2—C1—O12.3 (3)O3—C4—C5—C6174.7 (2)
Cl1—C2—C1—C6176.31 (17)O4—C6—C1—C2177.4 (2)
Cl1—C2—C3—O20.5 (3)O4—C6—C5—C4178.3 (2)
Cl1—C2—C3—C4179.34 (15)N1—C7—N2—C90.3 (3)
Cl2—C5—C4—O33.5 (3)N1—C8—C9—N20.3 (3)
Cl2—C5—C4—C3176.38 (16)N2—C7—N1—C80.1 (3)
Cl2—C5—C6—O40.1 (3)C1—C2—C3—C40.1 (3)
Cl2—C5—C6—C1179.41 (17)C1—C6—C5—C42.4 (4)
O1—C1—C2—C3178.2 (2)C2—C1—C6—C52.0 (3)
O1—C1—C6—O41.4 (3)C2—C3—C4—C54.2 (3)
O1—C1—C6—C5179.2 (2)C3—C2—C1—C63.1 (3)
O2—C3—C2—C1179.9 (2)C3—C4—C5—C65.4 (3)
O2—C3—C4—O34.3 (3)C7—N1—C8—C90.1 (3)
O2—C3—C4—C5175.7 (2)C7—N2—C9—C80.3 (3)
O3—C4—C3—C2175.9 (2)
Symmetry codes: (i) x, y, z; (ii) x1, y, z1; (iii) x, y, z1; (iv) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1···N30.86 (3)2.08 (3)2.827 (3)145 (3)
O4—H1···O10.86 (3)2.11 (3)2.613 (2)116 (2)
N1—H2···O10.94 (3)1.78 (3)2.703 (2)171 (3)
N2—H4···O2v0.95 (3)1.89 (3)2.773 (2)154 (2)
N2—H4···O3v0.95 (3)2.31 (3)2.974 (3)127 (2)
C11—H7···Cl2v0.88 (4)2.81 (5)3.507 (4)136 (4)
Symmetry code: (v) x+1, y, z+1.
 

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