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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 2C
3H
5N
2+·C
6Cl
2O
42−, and imidazolium chloroanilate acetonitrile solvate, C
3H
5N
2+·C
6HCl
2O
4−·C
2H
3N, (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
CCDC references: 163938; 163939; 163940
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.
Crystal data top
2C3H5N2+·C6Cl2O42− | 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) Å3 | Prismatic, brown |
Z = 2 | 0.45 × 0.40 × 0.30 mm |
Data collection top
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 top
Refinement on F2 | 0 constraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.050 | Weighting 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 = 1.43 | 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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Cl—C2 | 1.7409 (18) | C1—C2 | 1.403 (2) |
O1—C1 | 1.247 (2) | C1—C3i | 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···N2iv | 2.638 (2) |
O1···N2ii | 3.194 (2) | O2···N1i | 2.916 (2) |
O1···C6iii | 3.201 (3) | | |
| | | |
N2—N1—C6 | 109.31 (16) | O2—C3—C1i | 115.40 (15) |
N2—N1—H1 | 121.3 (19) | O2—C3—C2 | 125.80 (16) |
C6—N1—H1 | 129.0 (19) | C1i—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—C3i | 117.13 (14) | C4—C5—H4 | 130.4 (13) |
C2—C1—C3i | 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—C1i—C2i | 177.59 (15) |
Cl—C2—C1—C3i | 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—C1i | −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—C3i—O2i | 1.9 (2) | N2—C4—C5—C6 | −0.4 (2) |
O1—C1—C3i—C2i | −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) top
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···O2i | 0.88 (3) | 2.42 (3) | 2.916 (2) | 116 (2) |
N2—H2···O2iv | 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. |
Crystal data top
2C3H5N2+·C6Cl2O42− | 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) Å3 | Prismatic, brown |
Z = 2 | 0.50 × 0.30 × 0.20 mm |
Data collection top
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 top
Refinement on F2 | 0 constraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.051 | Weighting 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 = 1.35 | 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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C3i | 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···N1i | 2.924 (3) |
O1···C4ii | 3.121 (3) | O2···C4i | 3.174 (3) |
O1···C5iii | 3.295 (3) | O2···N1v | 3.206 (3) |
O2···N2iv | 2.712 (2) | | |
| | | |
C4—N1—C6 | 108.3 (2) | O2—C3—C1i | 115.75 (17) |
C4—N1—H1 | 126.8 (19) | O2—C3—C2 | 126.14 (19) |
C6—N1—H1 | 124.8 (19) | C1i—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—C3i | 117.02 (16) | N2—C5—H4 | 118.5 (15) |
C2—C1—C3i | 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—C1i—C2i | −178.38 (19) |
Cl—C2—C1—C3i | 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—C1i | −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—C3i—O2i | −2.6 (3) | C4—N1—C6—C5 | 0.3 (3) |
O1—C1—C3i—C2i | 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) top
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···O2i | 0.88 (3) | 2.30 (3) | 2.924 (2) | 127 (2) |
N2—H3···O2vi | 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. |
Crystal data top
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) Å3 | 0.50 × 0.30 × 0.25 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.052 | All H-atom parameters refined |
wR(F2) = 0.063 | Weighting scheme based on measured s.u.'s w = 1/[σ2(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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···C3iii | 3.239 (3) |
O1···N3 | 3.193 (3) | O3···N2ii | 2.974 (3) |
O1···C4i | 3.263 (3) | O3···C7ii | 3.168 (3) |
O2···N2ii | 2.773 (2) | O4···N3 | 2.827 (3) |
O2···C4iii | 3.095 (3) | N2···C1iv | 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) top
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···O2v | 0.95 (3) | 1.89 (3) | 2.773 (2) | 154 (2) |
N2—H4···O3v | 0.95 (3) | 2.31 (3) | 2.974 (3) | 127 (2) |
C11—H7···Cl2v | 0.88 (4) | 2.81 (5) | 3.507 (4) | 136 (4) |
Symmetry code: (v) x+1, y, z+1. |
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