Literature DB >> 21578928

Guanidinium quinoline-2-carboxyl-ate.

Graham Smith1, Urs D Wermuth.   

Abstract

In the structure of the guanidinium salt of quinaldic acid, CH(6)N(3) (+)·C(10)H(6)NO(2) (-), the asymmetric unit contains two independent cations and anions having similar inter-species hydrogen-bonding environments, which include cyclic R(2) (2)(8), R(2) (1)(6) and R(1) (2)(5) associations. These and additional weak aromatic ring π-π inter-actions [minimum ring-centroid separation = 3.662 (2) Å] give a two-dimensional layered structure.

Entities:  

Year:  2009        PMID： 21578928      PMCID： PMC2972072          DOI： 10.1107/S1600536809049733

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For guanidinium salts of aromatic acids, see: Parthasarathi et al. (1982 ▶); Schürmann et al. (1998 ▶); Najafpour et al. (2007 ▶); Pereira Silva et al. (2007 ▶). For quinaldic acid structures, see: Dobrzyńska & Jerzykiewicz (2004 ▶); Smith et al. (2004 ▶, 2007 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

CH6N3 +·C10H6NO2 − M = 232.25 Monoclinic, a = 7.4318 (3) Å b = 42.2105 (18) Å c = 7.3035 (4) Å β = 94.045 (4)° V = 2285.40 (18) Å3 Z = 8 Mo Kα radiation μ = 0.10 mm−1 T = 297 K 0.35 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.740, T max = 0.870 10626 measured reflections 3981 independent reflections 2931 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.069 wR(F 2) = 0.162 S = 1.04 3981 reflections 355 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.15 e Å−3 Δρmin = −0.18 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049733/wn2367sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049733/wn2367Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
CH6N3+·C10H6NO2−F(000) = 976
Mr = 232.25Dx = 1.350 Mg m−3
Monoclinic, P21/cMelting point = 543–544 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.4318 (3) ÅCell parameters from 4234 reflections
b = 42.2105 (18) Åθ = 2.9–28.8°
c = 7.3035 (4) ŵ = 0.10 mm−1
β = 94.045 (4)°T = 297 K
V = 2285.40 (18) Å3Prism, colourless
Z = 80.35 × 0.20 × 0.18 mm
Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer3981 independent reflections
Radiation source: Enhance (Mo) X-ray source2931 reflections with I > 2σ(I)
graphiteRint = 0.035
ω scansθmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.740, Tmax = 0.870k = −50→49
10626 measured reflectionsl = −8→8
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0614P)2 + 2.2259P] where P = (Fo2 + 2Fc2)/3
3981 reflections(Δ/σ)max = 0.003
355 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
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 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.
xyzUiso*/Ueq
O21A0.8508 (4)0.09058 (6)0.2611 (3)0.0621 (10)
O22A0.5996 (3)0.07308 (6)0.1162 (4)0.0645 (10)
N1A0.9927 (3)0.03079 (6)0.2631 (3)0.0344 (8)
C2A0.8222 (4)0.03520 (7)0.2056 (4)0.0347 (9)
C3A0.7048 (4)0.01015 (8)0.1538 (4)0.0432 (11)
C4A0.7670 (5)−0.02006 (8)0.1610 (4)0.0470 (11)
C5A1.0237 (5)−0.05662 (8)0.2320 (5)0.0526 (14)
C6A1.1980 (6)−0.06067 (9)0.2937 (5)0.0607 (14)
C7A1.3053 (5)−0.03505 (10)0.3470 (5)0.0573 (14)
C8A1.2375 (4)−0.00486 (8)0.3367 (4)0.0463 (11)
C9A1.0562 (4)0.00047 (7)0.2721 (4)0.0350 (10)
C10A0.9469 (4)−0.02599 (7)0.2209 (4)0.0386 (10)
C21A0.7531 (5)0.06891 (8)0.1948 (4)0.0434 (11)
O21B0.2113 (4)0.16103 (6)0.7760 (4)0.0595 (9)
O22B0.4256 (3)0.17922 (6)0.6099 (3)0.0547 (9)
N1B0.0628 (3)0.22063 (6)0.7787 (3)0.0337 (8)
C2B0.2260 (4)0.21671 (7)0.7234 (4)0.0331 (9)
C3B0.3404 (4)0.24202 (7)0.6830 (4)0.0383 (10)
C4B0.2823 (4)0.27223 (7)0.7016 (4)0.0399 (10)
C5B0.0359 (5)0.30838 (8)0.7780 (4)0.0467 (11)
C6B−0.1343 (5)0.31222 (9)0.8310 (5)0.0521 (12)
C7B−0.2392 (5)0.28594 (9)0.8685 (5)0.0500 (11)
C8B−0.1739 (4)0.25609 (8)0.8528 (4)0.0417 (11)
C9B0.0024 (4)0.25108 (7)0.7961 (4)0.0326 (9)
C10B0.1082 (4)0.27776 (7)0.7584 (4)0.0360 (10)
C21B0.2913 (4)0.18309 (8)0.7021 (4)0.0389 (10)
N1C0.1537 (5)0.11364 (9)0.4833 (5)0.0598 (12)
N2C0.2735 (5)0.08075 (8)0.2766 (5)0.0671 (14)
N3C0.4496 (5)0.11943 (9)0.4200 (5)0.0622 (12)
C1C0.2924 (5)0.10473 (8)0.3933 (5)0.0506 (11)
N1D0.6118 (5)0.13337 (8)−0.0734 (5)0.0553 (11)
N2D0.9196 (5)0.13416 (8)−0.0311 (5)0.0500 (11)
N3D0.7754 (5)0.17077 (7)−0.2190 (4)0.0554 (11)
C1D0.7690 (5)0.14616 (7)−0.1083 (4)0.0415 (11)
H3A0.585200.014300.114900.0520*
H4A0.69050−0.036800.126200.0560*
H5A0.95370−0.074100.196600.0630*
H6A1.24640−0.081000.300400.0730*
H7A1.42460−0.038300.390200.0680*
H8A1.311100.012200.372400.0560*
H3B0.454600.238000.643900.0460*
H4B0.357100.289100.677100.0480*
H5B0.105300.326100.754500.0560*
H6B−0.181200.332500.842300.0630*
H7B−0.355500.288900.904700.0600*
H8B−0.245300.238800.879400.0500*
H11C0.165 (4)0.1267 (8)0.567 (5)0.070 (10)*
H12C0.046 (6)0.1036 (9)0.454 (5)0.066 (12)*
H21C0.376 (6)0.0750 (10)0.217 (6)0.079 (13)*
H22C0.173 (6)0.0684 (11)0.272 (6)0.084 (14)*
H31C0.448 (6)0.1394 (11)0.475 (6)0.089 (15)*
H32C0.540 (6)0.1136 (11)0.367 (6)0.081 (15)*
H11D0.611 (5)0.1156 (10)−0.014 (5)0.068 (13)*
H12D0.514 (6)0.1421 (11)−0.114 (7)0.091 (17)*
H21D1.022 (5)0.1409 (8)−0.055 (5)0.064 (10)*
H22D0.908 (6)0.1206 (11)0.060 (6)0.083 (15)*
H31D0.882 (5)0.1819 (9)−0.227 (5)0.060 (11)*
H32D0.670 (6)0.1793 (10)−0.273 (6)0.074 (13)*
U11U22U33U12U13U23
O21A0.087 (2)0.0395 (15)0.0588 (15)0.0029 (13)−0.0028 (14)0.0009 (11)
O22A0.0422 (15)0.0608 (17)0.092 (2)0.0122 (12)0.0149 (14)0.0230 (14)
N1A0.0365 (15)0.0328 (14)0.0346 (13)−0.0010 (11)0.0068 (11)0.0000 (10)
C2A0.0352 (17)0.0373 (17)0.0327 (15)−0.0018 (13)0.0111 (13)0.0042 (12)
C3A0.0356 (18)0.051 (2)0.0428 (18)−0.0015 (15)0.0006 (14)0.0001 (15)
C4A0.053 (2)0.043 (2)0.0449 (19)−0.0100 (16)0.0020 (16)−0.0061 (15)
C5A0.076 (3)0.038 (2)0.0444 (19)0.0035 (18)0.0089 (18)−0.0019 (15)
C6A0.085 (3)0.048 (2)0.050 (2)0.021 (2)0.011 (2)0.0060 (17)
C7A0.055 (2)0.070 (3)0.047 (2)0.021 (2)0.0044 (17)0.0106 (18)
C8A0.044 (2)0.053 (2)0.0422 (18)0.0029 (16)0.0050 (15)0.0034 (15)
C9A0.0405 (18)0.0378 (18)0.0275 (15)0.0017 (14)0.0073 (13)0.0031 (12)
C10A0.052 (2)0.0339 (18)0.0306 (15)−0.0008 (14)0.0090 (14)−0.0004 (12)
C21A0.046 (2)0.044 (2)0.0421 (18)0.0062 (16)0.0173 (15)0.0097 (15)
O21B0.0687 (17)0.0414 (14)0.0712 (16)0.0055 (13)0.0246 (13)0.0069 (12)
O22B0.0368 (13)0.0508 (15)0.0783 (17)0.0036 (11)0.0159 (12)−0.0133 (12)
N1B0.0309 (14)0.0378 (15)0.0322 (13)0.0010 (11)0.0002 (10)−0.0030 (10)
C2B0.0286 (16)0.0401 (17)0.0304 (15)0.0018 (13)−0.0002 (12)−0.0051 (12)
C3B0.0292 (16)0.048 (2)0.0376 (16)−0.0003 (14)0.0027 (13)−0.0049 (14)
C4B0.0376 (18)0.0414 (19)0.0407 (17)−0.0082 (14)0.0023 (14)−0.0013 (13)
C5B0.055 (2)0.0376 (19)0.0469 (19)0.0029 (16)0.0004 (16)0.0021 (14)
C6B0.059 (2)0.044 (2)0.053 (2)0.0182 (18)0.0010 (17)−0.0025 (16)
C7B0.043 (2)0.061 (2)0.0462 (19)0.0124 (17)0.0039 (15)−0.0062 (16)
C8B0.0366 (18)0.048 (2)0.0406 (18)0.0015 (15)0.0027 (14)−0.0039 (14)
C9B0.0301 (16)0.0402 (18)0.0268 (14)0.0026 (13)−0.0032 (12)−0.0033 (12)
C10B0.0382 (17)0.0405 (18)0.0286 (15)0.0010 (14)−0.0028 (12)−0.0013 (12)
C21B0.0332 (17)0.0404 (19)0.0425 (17)0.0017 (14)−0.0007 (14)−0.0025 (14)
N1C0.060 (2)0.054 (2)0.068 (2)−0.0068 (18)0.0225 (18)−0.0130 (17)
N2C0.055 (2)0.052 (2)0.098 (3)−0.0159 (17)0.032 (2)−0.0300 (18)
N3C0.055 (2)0.050 (2)0.084 (2)−0.0109 (17)0.0209 (18)−0.0184 (17)
C1C0.056 (2)0.0367 (19)0.061 (2)−0.0033 (17)0.0166 (18)0.0032 (16)
N1D0.050 (2)0.0452 (19)0.071 (2)−0.0032 (16)0.0071 (16)0.0158 (16)
N2D0.047 (2)0.0478 (19)0.0550 (19)−0.0004 (16)0.0023 (15)0.0055 (15)
N3D0.047 (2)0.0462 (19)0.072 (2)−0.0081 (16)−0.0022 (16)0.0205 (15)
C1D0.046 (2)0.0344 (18)0.0445 (18)−0.0033 (15)0.0051 (15)−0.0031 (14)
O21A—C21A1.245 (4)C4A—C10A1.400 (5)
O22A—C21A1.253 (4)C5A—C6A1.352 (6)
O21B—C21B1.248 (4)C5A—C10A1.413 (5)
O22B—C21B1.253 (4)C6A—C7A1.383 (6)
N1A—C2A1.320 (4)C7A—C8A1.371 (5)
N1A—C9A1.364 (4)C8A—C9A1.414 (4)
N1B—C2B1.316 (4)C9A—C10A1.416 (4)
N1B—C9B1.370 (4)C3A—H3A0.9300
N1C—C1C1.316 (5)C4A—H4A0.9300
N2C—C1C1.324 (5)C5A—H5A0.9300
N3C—C1C1.325 (5)C6A—H6A0.9300
N1C—H11C0.82 (4)C7A—H7A0.9300
N1C—H12C0.92 (4)C8A—H8A0.9300
N2C—H21C0.94 (4)C2B—C21B1.511 (4)
N2C—H22C0.91 (4)C2B—C3B1.410 (4)
N3C—H32C0.84 (4)C3B—C4B1.356 (4)
N3C—H31C0.93 (5)C4B—C10B1.406 (4)
N1D—C1D1.328 (5)C5B—C10B1.411 (5)
N2D—C1D1.318 (5)C5B—C6B1.358 (5)
N3D—C1D1.319 (4)C6B—C7B1.394 (5)
N1D—H11D0.87 (4)C7B—C8B1.358 (5)
N1D—H12D0.85 (5)C8B—C9B1.418 (4)
N2D—H21D0.84 (4)C9B—C10B1.412 (4)
N2D—H22D0.89 (4)C3B—H3B0.9300
N3D—H31D0.93 (4)C4B—H4B0.9300
N3D—H32D0.93 (4)C5B—H5B0.9300
C2A—C21A1.513 (5)C6B—H6B0.9300
C2A—C3A1.406 (4)C7B—H7B0.9300
C3A—C4A1.356 (5)C8B—H8B0.9300
O21A···N1A2.735 (4)C10B···C2Bv3.455 (4)
O21A···N1Ci2.852 (5)C10B···C3Bv3.541 (4)
O21A···N2Ci3.163 (5)C21B···C5Bxi3.535 (4)
O21A···N2D2.890 (4)C1D···H6Ax3.0900
O21A···C1Ci3.408 (5)C2A···H22Ci2.97 (5)
O21B···N1C2.937 (5)C2B···H31Dii2.99 (4)
O21B···N2Dii2.899 (5)C3A···H3Axiii2.9900
O21B···N1B2.748 (4)C4B···H7Bi3.0600
O21B···N3Dii3.268 (5)C9A···H22Ci3.00 (5)
O22A···N3C3.216 (5)C9B···H31Dii3.06 (4)
O22A···N1D2.902 (4)C21A···H21C2.83 (4)
O22A···N2C2.784 (4)C21A···H32C2.82 (5)
O22B···N1Diii3.250 (4)C21A···H11D2.66 (4)
O22B···N3C2.891 (4)C21A···H22D2.69 (5)
O22B···N3Diii2.826 (4)C21B···H11C2.72 (3)
O21A···H12Ci2.03 (4)C21B···H31C2.79 (5)
O21A···H11D2.80 (4)C21B···H32Diii2.81 (4)
O21A···H22Ci2.57 (4)C21B···H12Diii2.69 (5)
O21A···H32C2.67 (5)H3A···O22A2.4800
O21A···H22D2.01 (5)H3A···C3Axiii2.9900
O21B···H21Dii2.11 (4)H3A···H3Axiii2.3600
O21B···H31Dii2.60 (4)H3B···H7Biv2.5800
O21B···H11C2.12 (4)H3B···O22B2.5000
O21B···H12Diii2.47 (5)H4A···H5A2.5400
O22A···H3A2.4800H4B···H5B2.5300
O22A···H32C2.57 (5)H5A···H4A2.5400
O22A···H11D2.04 (4)H5B···H4B2.5300
O22A···H21C1.87 (4)H5B···N2Dxii2.9400
O22B···H12Diii2.60 (5)H6A···C1Dx3.0900
O22B···H7Biv2.6500H7B···H3Bxii2.5800
O22B···H31C1.96 (5)H7B···C4Bvi3.0600
O22B···H32Diii1.95 (4)H7B···O22Bxii2.6500
O22B···H3B2.5000H11C···C21B2.72 (3)
N1A···O21A2.735 (4)H11C···O21B2.12 (4)
N1A···N2Ci2.964 (4)H11C···H31C2.32 (5)
N1B···O21B2.748 (4)H11D···H22D2.25 (6)
N1B···N3Dii3.000 (4)H11D···C21A2.66 (4)
N1B···C4Bv3.403 (4)H11D···O21A2.80 (4)
N1C···O21B2.937 (5)H11D···O22A2.04 (4)
N1C···O21Avi2.852 (5)H12C···H22C2.25 (6)
N1D···O22A2.902 (4)H12C···O21Avi2.03 (4)
N1D···O22Bvii3.250 (4)H12D···O21Bvii2.47 (5)
N2C···N1Avi2.964 (4)H12D···C21Bvii2.69 (5)
N2C···O21Avi3.163 (5)H12D···H32D2.31 (6)
N2C···O22A2.784 (4)H12D···O22Bvii2.60 (5)
N2D···C5Biv3.384 (5)H21C···C21A2.83 (4)
N2D···O21Bviii2.899 (5)H21C···H32C2.27 (6)
N2D···O21A2.890 (4)H21C···O22A1.87 (4)
N3C···O22B2.891 (4)H21D···O21Bviii2.11 (4)
N3C···O22A3.216 (5)H21D···H31D2.34 (5)
N3D···O22Bvii2.826 (4)H22C···C2Avi2.97 (5)
N3D···O21Bviii3.268 (5)H22C···C9Avi3.00 (5)
N3D···N1Bviii3.000 (4)H22C···H12C2.25 (6)
N1A···H22Ci2.08 (5)H22C···N1Avi2.08 (5)
N1B···H31Dii2.12 (4)H22C···O21Avi2.57 (4)
N2D···H5Biv2.9400H22D···O21A2.01 (5)
C1C···O21Avi3.408 (5)H22D···C21A2.69 (5)
C2A···C7Aix3.466 (5)H22D···H11D2.25 (6)
C2A···C5Ax3.586 (5)H31C···C21B2.79 (5)
C2B···C10Bxi3.455 (4)H31C···H11C2.32 (5)
C2B···C4Bv3.519 (4)H31C···O22B1.96 (5)
C3B···C4Bxi3.563 (4)H31D···H21D2.34 (5)
C3B···C10Bxi3.541 (4)H31D···O21Bviii2.60 (4)
C4B···C2Bxi3.519 (4)H31D···N1Bviii2.12 (4)
C4B···C3Bv3.563 (4)H31D···C9Bviii3.06 (4)
C4B···N1Bxi3.403 (4)H31D···C2Bviii2.99 (4)
C5A···C2Ax3.586 (5)H32C···C21A2.82 (5)
C5B···C21Bv3.535 (4)H32C···H21C2.27 (6)
C5B···N2Dxii3.384 (5)H32C···O22A2.57 (5)
C7A···C2Aix3.466 (5)H32C···O21A2.67 (5)
C8B···C9Bv3.419 (4)H32D···O22Bvii1.95 (4)
C9A···C9Aix3.489 (4)H32D···C21Bvii2.81 (4)
C9B···C8Bxi3.419 (4)H32D···H12D2.31 (6)
C2A—N1A—C9A118.0 (3)C6A—C5A—H5A120.00
C2B—N1B—C9B117.5 (3)C7A—C6A—H6A120.00
C1C—N1C—H11C121 (2)C5A—C6A—H6A119.00
C1C—N1C—H12C117 (3)C8A—C7A—H7A120.00
H11C—N1C—H12C122 (3)C6A—C7A—H7A120.00
C1C—N2C—H21C116 (3)C7A—C8A—H8A120.00
C1C—N2C—H22C121 (3)C9A—C8A—H8A120.00
H21C—N2C—H22C122 (4)N1B—C2B—C21B117.4 (3)
C1C—N3C—H31C117 (3)C3B—C2B—C21B119.2 (3)
C1C—N3C—H32C122 (3)N1B—C2B—C3B123.5 (3)
H31C—N3C—H32C120 (4)C2B—C3B—C4B119.4 (3)
C1D—N1D—H11D119 (2)C3B—C4B—C10B119.5 (3)
C1D—N1D—H12D120 (3)C6B—C5B—C10B120.5 (3)
H11D—N1D—H12D121 (4)C5B—C6B—C7B120.4 (3)
C1D—N2D—H22D116 (3)C6B—C7B—C8B120.9 (3)
H21D—N2D—H22D121 (4)C7B—C8B—C9B120.4 (3)
C1D—N2D—H21D122 (2)C8B—C9B—C10B118.5 (3)
C1D—N3D—H31D120 (2)N1B—C9B—C8B118.9 (3)
C1D—N3D—H32D120 (3)N1B—C9B—C10B122.7 (3)
H31D—N3D—H32D119 (4)C4B—C10B—C9B117.5 (3)
N1A—C2A—C21A117.7 (3)C5B—C10B—C9B119.3 (3)
N1A—C2A—C3A122.9 (3)C4B—C10B—C5B123.2 (3)
C3A—C2A—C21A119.4 (3)O21B—C21B—C2B119.3 (3)
C2A—C3A—C4A119.6 (3)O21B—C21B—O22B123.8 (3)
C3A—C4A—C10A119.7 (3)O22B—C21B—C2B116.8 (3)
C6A—C5A—C10A120.6 (3)C2B—C3B—H3B120.00
C5A—C6A—C7A121.0 (4)C4B—C3B—H3B120.00
C6A—C7A—C8A120.6 (3)C10B—C4B—H4B120.00
C7A—C8A—C9A120.3 (3)C3B—C4B—H4B120.00
N1A—C9A—C10A122.5 (3)C6B—C5B—H5B120.00
N1A—C9A—C8A118.9 (3)C10B—C5B—H5B120.00
C8A—C9A—C10A118.6 (3)C7B—C6B—H6B120.00
C5A—C10A—C9A119.0 (3)C5B—C6B—H6B120.00
C4A—C10A—C9A117.3 (3)C8B—C7B—H7B120.00
C4A—C10A—C5A123.7 (3)C6B—C7B—H7B120.00
O21A—C21A—C2A119.0 (3)C9B—C8B—H8B120.00
O21A—C21A—O22A124.2 (3)C7B—C8B—H8B120.00
O22A—C21A—C2A116.8 (3)N2C—C1C—N3C120.3 (4)
C2A—C3A—H3A120.00N1C—C1C—N2C119.3 (4)
C4A—C3A—H3A120.00N1C—C1C—N3C120.4 (3)
C3A—C4A—H4A120.00N2D—C1D—N3D119.9 (3)
C10A—C4A—H4A120.00N1D—C1D—N2D119.6 (3)
C10A—C5A—H5A120.00N1D—C1D—N3D120.5 (3)
C9A—N1A—C2A—C3A0.0 (4)N1A—C9A—C10A—C5A179.2 (3)
C9A—N1A—C2A—C21A−179.6 (2)C8A—C9A—C10A—C4A178.7 (3)
C2A—N1A—C9A—C8A−178.8 (3)C8A—C9A—C10A—C5A−1.5 (4)
C2A—N1A—C9A—C10A0.6 (4)N1A—C9A—C10A—C4A−0.6 (4)
C2B—N1B—C9B—C8B179.1 (3)N1B—C2B—C3B—C4B0.2 (5)
C2B—N1B—C9B—C10B−0.4 (4)C21B—C2B—C3B—C4B179.9 (3)
C9B—N1B—C2B—C3B0.4 (4)N1B—C2B—C21B—O21B−16.7 (4)
C9B—N1B—C2B—C21B−179.3 (2)N1B—C2B—C21B—O22B163.6 (3)
C3A—C2A—C21A—O21A171.5 (3)C3B—C2B—C21B—O21B163.6 (3)
N1A—C2A—C21A—O21A−8.9 (4)C3B—C2B—C21B—O22B−16.1 (4)
N1A—C2A—C21A—O22A170.3 (3)C2B—C3B—C4B—C10B−0.9 (4)
N1A—C2A—C3A—C4A−0.5 (5)C3B—C4B—C10B—C5B−178.8 (3)
C21A—C2A—C3A—C4A179.1 (3)C3B—C4B—C10B—C9B0.9 (4)
C3A—C2A—C21A—O22A−9.4 (4)C10B—C5B—C6B—C7B0.6 (5)
C2A—C3A—C4A—C10A0.4 (4)C6B—C5B—C10B—C4B179.1 (3)
C3A—C4A—C10A—C9A0.1 (4)C6B—C5B—C10B—C9B−0.6 (5)
C3A—C4A—C10A—C5A−179.7 (3)C5B—C6B—C7B—C8B−0.1 (5)
C6A—C5A—C10A—C4A−179.0 (3)C6B—C7B—C8B—C9B−0.6 (5)
C6A—C5A—C10A—C9A1.2 (5)C7B—C8B—C9B—N1B−178.9 (3)
C10A—C5A—C6A—C7A−0.1 (6)C7B—C8B—C9B—C10B0.6 (4)
C5A—C6A—C7A—C8A−0.6 (6)N1B—C9B—C10B—C4B−0.2 (4)
C6A—C7A—C8A—C9A0.3 (5)N1B—C9B—C10B—C5B179.5 (3)
C7A—C8A—C9A—N1A−179.9 (3)C8B—C9B—C10B—C4B−179.7 (3)
C7A—C8A—C9A—C10A0.8 (4)C8B—C9B—C10B—C5B0.0 (4)
D—H···AD—HH···AD···AD—H···A
N1C—H11C···O21B0.82 (4)2.12 (4)2.937 (5)176 (3)
N1C—H12C···O21Avi0.92 (4)2.03 (4)2.852 (5)149 (3)
N1D—H11D···O22A0.87 (4)2.04 (4)2.902 (4)177 (4)
N1D—H12D···O21Bvii0.85 (5)2.47 (5)3.312 (5)173 (4)
N2C—H21C···O22A0.94 (4)1.87 (4)2.784 (4)166 (4)
N2C—H22C···O21Avi0.91 (4)2.57 (4)3.163 (5)124 (4)
N2C—H22C···N1Avi0.91 (4)2.08 (5)2.964 (4)165 (4)
N2D—H21D···O21Bviii0.84 (4)2.11 (4)2.899 (5)155 (3)
N2D—H22D···O21A0.89 (4)2.01 (5)2.890 (4)173 (4)
N3C—H31C···O22B0.93 (5)1.96 (5)2.891 (4)173 (4)
N3C—H32C···O22A0.84 (4)2.57 (5)3.216 (5)135 (4)
N3D—H31D···O21Bviii0.93 (4)2.60 (4)3.268 (5)130 (3)
N3D—H31D···N1Bviii0.93 (4)2.12 (4)3.000 (4)159 (3)
N3D—H32D···O22Bvii0.93 (4)1.95 (4)2.826 (4)157 (4)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1C—H11C⋯O21B 0.82 (4)2.12 (4)2.937 (5)176 (3)
N1C—H12C⋯O21A i 0.92 (4)2.03 (4)2.852 (5)149 (3)
N1D—H11D⋯O22A 0.87 (4)2.04 (4)2.902 (4)177 (4)
N1D—H12D⋯O21B ii 0.85 (5)2.47 (5)3.312 (5)173 (4)
N2C—H21C⋯O22A 0.94 (4)1.87 (4)2.784 (4)166 (4)
N2C—H22C⋯O21A i 0.91 (4)2.57 (4)3.163 (5)124 (4)
N2C—H22C⋯N1A i 0.91 (4)2.08 (5)2.964 (4)165 (4)
N2D—H21D⋯O21B iii 0.84 (4)2.11 (4)2.899 (5)155 (3)
N2D—H22D⋯O21A 0.89 (4)2.01 (5)2.890 (4)173 (4)
N3C—H31C⋯O22B 0.93 (5)1.96 (5)2.891 (4)173 (4)
N3C—H32C⋯O22A 0.84 (4)2.57 (5)3.216 (5)135 (4)
N3D—H31D⋯O21B iii 0.93 (4)2.60 (4)3.268 (5)130 (3)
N3D—H31D⋯N1B iii 0.93 (4)2.12 (4)3.000 (4)159 (3)
N3D—H32D⋯O22B ii 0.93 (4)1.95 (4)2.826 (4)157 (4)

Symmetry codes: (i) ; (ii) ; (iii) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  One-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with 8-hydroxyquinoline, 8-aminoquinoline and quinoline-2-carboxylic acid (quinaldic acid).

Authors:  Graham Smith; Urs D Wermuth; Jonathan M White
Journal:  Acta Crystallogr C       Date:  2008-02-23       Impact factor: 1.172

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  3 in total

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