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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 12| December 2013| Pages o1773-o1774
doi:10.1107/S1600536813030274

(E)-2-[2-(4-Carb­­oxy­phen­yl)ethen­yl]-8-hy­droxy­quinolin-1-ium chloride ethanol monosolvate

Mathias M. Schulze,a Wilhelm Seichtera and Edwin Webera*

aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
*Correspondence e-mail: edwin.weber@chemie-tu.freiberg.de

(Received 29 October 2013; accepted 5 November 2013; online 13 November 2013)

In the title compound, C18H14NO3+·Cl−·CH3CH2OH, the dihedral angle formed by the mean planes of the quinolinium and benzene rings is 3.4 (1)°, while the carb­oxy substituent is tilted at an angle of 4.8 (1)° with respect to the benzene ring. There is a short N—H⋯O contact in the cation. In the crystal, due to the planar mol­ecular geometry, two-dimensional aggregates are formed parallel to (221) via C—H⋯O, C—H⋯Cl, O—H⋯Cl and N—H⋯Cl hydrogen bonds. Inter­layer association is accomplished by O—Hethanol⋯Cl and O—H⋯Oethanol hydrogen bonds and π–π stacking inter­actions [centroid–centroid distances vary from 3.6477 (12) to 3.8381 (11) Å]. A supra­molecular three-dimensional architecture results from a stacked arrangement of layers comprising the ionic and hydrogen-bonded components.

CCDC reference: 970296

Related literature

For metal-organic framework construction, see: MacGillivray (2010[MacGillivray, L. R. (2010). Editor. Metal-Organic Frameworks. Hoboken: Wiley.]); Noro & Kitagawa (2010[Noro, S. & Kitagawa, S. (2010). The Supramolecular Chemistry of Organic-Inorganic Hybrid Materials, edited by K. Rurack & R. Martínez-Máñez, pp. 235-269. Hoboken: Wiley.]). For complexation of quinolin-8-ol and its derivatives, see: Albrecht et al. (2008[Albrecht, M., Fiege, M. & Osetska, O. (2008). Coord. Chem. Rev. 252, 812-824.]); Weber & Vögtle (1975[Weber, E. & Vögtle, F. (1975). Tetrahedron Lett. pp. 2415-2418.]). For coordination behavior of carb­oxy­lic groups, see: Kitagawa et al. (2004[Kitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334-2375.]); Böhle et al. (2011[Böhle, T., Eissmann, F., Weber, E. & Mertens, F. O. R. L. (2011). Acta Cryst. C67, m5-m8.]). For the preparative method used for the synthesis of the title compound, see: Yuan et al. (2012[Yuan, G.-Z., Rong, L.-L., Huo, Y.-P., Nie, X.-L. & Fang, X.-M. (2012). Inorg. Chem. Commun. 23, 90-94.]). For related structures of quinolinol derivatives, see: Tan (2007[Tan, T. (2007). J. Mol. Struct. 840, 6-13.]); Zinczuk et al. (2008[Zinczuk, J., Piro, O. E., Castellano, E. E. & Baran, E. J. (2008). J. Mol. Struct. 892, 216-219.]). For non-classical hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. Oxford University Press.]). For π–π stacking inter­actions, see: James (2004[James, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093-1099. Boca Raton: CRC Press.]).

[Scheme 1]

Experimental

Crystal data

  • C18H14NO3+·Cl−·C2H6O

  • Mr = 373.82

  • Triclinic, [P \overline 1]

  • a = 9.6841 (2) Å

  • b = 9.7030 (2) Å

  • c = 10.8456 (3) Å

  • α = 67.516 (1)°

  • β = 74.957 (1)°

  • γ = 86.249 (1)°

  • V = 908.72 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 173 K

  • 0.28 × 0.19 × 0.05 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.937, Tmax = 0.988

  • 19296 measured reflections

  • 3596 independent reflections

  • 2790 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.147

  • S = 1.10

  • 3596 reflections

  • 243 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O1 0.91 (2) 2.27 (2) 2.678 (2) 107 (2)
O1—H1⋯Cl1i 0.82 2.26 3.0780 (16) 173
N1—H1A⋯Cl1ii 0.91 (2) 2.38 (2) 3.2087 (18) 151 (2)
O1G—H1G⋯Cl1 0.82 2.26 3.076 (3) 179
O2—H2A⋯O1Giii 0.82 1.85 2.634 (3) 159
C4—H4⋯O3iv 0.93 2.46 3.295 (3) 150
C10—H10⋯Cl1ii 0.93 2.69 3.446 (2) 138
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x, y, z+1; (iii) x+1, y+1, z; (iv) x-1, y-1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 970296

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813030274/su2663sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813030274/su2663Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813030274/su2663Isup3.cml

checkCIF report


Comment top

Bifunctional organic ligands have proven very efficient building units in the construction of metal-organic frameworks (MOFs) (MacGillivray, 2010). In particular, one may expect new MOF-architectures from ligands comprising two different coordination sites (Noro et al., 2010). Due to the well known complexation properties of quinolin-8-ol (Albrecht et al., 2008; Weber & Vögtle, 1975) and taking into account the commonly noted coordination behaviour of carboxylic acid groups to various metal ions (Kitagawa et al., 2004; Böhle et al., 2011), corresponding ligands featuring both these structural elements are rated high in this connection. Preparation of a respective hetero bifunctional ligand led to the formation of the title compound. This was isolated as crystals which were found to be a hydrochloride salt containing included ethanol.

In the structure of the title compound (Fig. 1), the principal molecule has an E configuration with reference to the ethenyl bond, C10═C11. The overall geometry of this molecule shows approximate planarity with the largest atomic distance from the mean plane of the quinolinium moiety (N1/C1-C9) being -0.018 (1) Å for C8 and 0.011 (2) Å for C9, whereas the phenyl ring (C12-C17 ) is perfectly planar. The dihedral angle between the mean planes of these aromatic building blocks is 3.4 (1) °, while the carboxy substituent (C18/O2/O3) is inclined at an angle of 4.8 (4) ° referring to the phenyl ring. The bond distances within the quinolinium moiety are within expected values (Tan, 2007; Zinczuk et al., 2008).

The chloride ion, Cl1, can be considered as a nodal point within the coordination pattern of the molecules as it is connected with the hydroxy hydrogen [O1—H1···Cl1 2.26 Å, 173 °], the quinolinium hydrogen [N1—H1 A···Cl1 2.38 (2) Å, 151 (2) °] and more weakly (Desiraju & Steiner, 1999) to an ethenyl hydrogen [C10—H10···Cl1 2.69 Å, 138 °] of two different cations. Details are given in Fig. 2 and Table 1. In addition, one molecule of solvent (EtOH) is coordinated by its hydroxy hydrogen to the anion [O1G—H1G···Cl1 2.26 Å, 179 °; see Table 1 and Fig. 2].

In the crystal, there is a layered arrangement of molecules, which apart from the ionic interactions is stabilized by conventional N-H···O and O-H···O hydrogen bonds (Fig. 2 and Table 1). Moreover, in the stacking direction of the molecular layers the mean distance of 3.50 Å between consecutive molecules and the overlap of their aromatic units suggest the presence of π–π interactions (James, 2004). These include Cg1···Cg1i = 3.7477 (12) Å, normal distance = 3.3605 (8) Å, slippage = 1.659 Å; Cg1···Cg2i = 3.8381 (11) Å; Cg1···Cg3ii = 3.6477 (12) Å; Cg2···Cg3ii = 3.7241 (12) Å [Cg1, Cg2 and Cg3 are the centroids of rings C5-C8/N1/C9, C1-C5/C9 and C12-C17, respectively; symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+1, -y+1, -z+2].

Related literature top

For metal-organic framework construction, see: MacGillivray (2010); Noro & Kitagawa (2010). For complexation of quinolin-8-ol and its derivatives, see: Albrecht et al. (2008); Weber & Vögtle (1975). For coordination behavior of carboxylic groups, see: Kitagawa et al. (2004); Böhle et al. (2011). For the preparative method used for the synthesis of the title compound, see: Yuan et al. (2012). For related structures of quinolinol derivatives, see: Tan (2007); Zinczuk et al. (2008). For non-classical hydrogen bonds, see: Desiraju & Steiner (1999). For π–π stacking interactions, see: James (2004).

Experimental top

The title compound was synthesized via Knoevenagel type condensation (Yuan et al., 2012) using 8-hydroxyquinaldine (320 mg, 2.0 mmol) and 4-formylbenzoic acid (1.20 g, 8.0 mmol) in acetic anhydride (100 ml). The mixture was stirred for 30 h under reflux. After removal of the solvent, the residue was dissolved in 100 ml of pyridine/water (v/v = 4:1) and heated at 373 K for 1 h. Evaporation of the solvent under vacuum and purification of the crude product by recrystallization from ethanol and treatment with hydrochloric acid (37%) yielded 370 mg (63%) of the title compound as brown crystals. The E configuration of the compound was confirmed by 1H NMR analysis (ethenylene protons); M. p. = 514 K.; MS (ESI) m/z: found 292.0 [M+H]+; calc. for C18H18NO3 291.09. Spectroscopic data, including IR and 1H and 13C NMR, for the title compound are available in the archived CIF.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The NH hydrogen was located in a difference Fourier map and freely refined. All other H atoms were positioned geometrically and constrained to ride on their respective parent atoms: O—H = 0.82 Å, C—H = 0.93, 0.96 and 0.97 Å for aryl/ethenyl, methylene and methyl H atoms, respectively, with Uiso(H) = 1.5Ueq(C-methyl and O), and = 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines (see Table 1 for details).
[Figure 2] Fig. 2. A partial view of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines within the layer motif (see Table 1 for details).
(E)-2-[2-(4-Carboxyphenyl)ethenyl]-8-hydroxyquinolin-1-ium chloride ethanol monosolvate top
Crystal data top
C18H14NO3+·Cl−·C2H6OZ = 2
Mr = 373.82F(000) = 392
Triclinic, P1Dx = 1.366 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6841 (2) ÅCell parameters from 6622 reflections
b = 9.7030 (2) Åθ = 2.3–28.5°
c = 10.8456 (3) ŵ = 0.24 mm−1
α = 67.516 (1)°T = 173 K
β = 74.957 (1)°Plate, colourless
γ = 86.249 (1)°0.28 × 0.19 × 0.05 mm
V = 908.72 (4) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3596 independent reflections
Radiation source: fine-focus sealed tube2790 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
phi and ω scansθmax = 26.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −11→11
Tmin = 0.937, Tmax = 0.988k = −12→12
19296 measured reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0792P)2 + 0.2177P]
where P = (Fo2 + 2Fc2)/3
3596 reflections(Δ/σ)max = 0.001
243 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C18H14NO3+·Cl−·C2H6Oγ = 86.249 (1)°
Mr = 373.82V = 908.72 (4) Å3
Triclinic, P1Z = 2
a = 9.6841 (2) ÅMo Kα radiation
b = 9.7030 (2) ŵ = 0.24 mm−1
c = 10.8456 (3) ÅT = 173 K
α = 67.516 (1)°0.28 × 0.19 × 0.05 mm
β = 74.957 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3596 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		2790 reflections with I > 2σ(I)
Tmin = 0.937, Tmax = 0.988Rint = 0.022
19296 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.43 e Å−3
3596 reflectionsΔρmin = −0.32 e Å−3
243 parameters
Special details top

Experimental. Spectroscopic data for the title compound:

IR (KBr, cm-1) 3354, 2810, 2537, 1673, 1284, 1194, 882, 747, 541. 1H NMR (500 MHz, DMSO-d6) 7.07 (d, 3JHH = 7.3 Hz, 1 H), 7.30 (d, 3JHH = 8.0 Hz, 1 H), 7.36 (t, 3JHH = 7.8 Hz, 1 H), 7.52 (d, 3JHH = 16.2 Hz, 1 H), 7.80–7.68 (m, 3H), 7.98 (d, 3JHH = 8.0 Hz, 2 H), 8.13–8.07 (m, 1H), 8.21 (d, 3JHH = 8.5 Hz, 1 H), 9.39 (br s, 1 H). 13C NMR (126 MHz, DMSO-d6) 110.9, 117.4, 120.9, 126.9, 127.1, 127.7, 129.2, 129.8, 130.1, 130.4, 133.1, 136.4, 140.6, 152.8, 152.9, 167.0.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.43522 (18)−0.02294 (17)1.40451 (15)0.0570 (4)
H10.4203−0.09531.47780.085*
O21.15248 (18)1.03920 (17)0.62269 (16)0.0589 (4)
H2A1.21701.09780.60950.088*
O31.1812 (2)0.9480 (2)0.83527 (18)0.0734 (5)
N10.49743 (17)0.17149 (17)1.14211 (16)0.0368 (4)
H1A0.534 (2)0.175 (2)1.210 (2)0.040 (5)*
C10.3645 (2)−0.0445 (2)1.3210 (2)0.0424 (5)
C20.2652 (2)−0.1571 (2)1.3597 (2)0.0483 (5)
H20.2427−0.22671.45000.058*
C30.1975 (2)−0.1685 (2)1.2652 (2)0.0507 (5)
H30.1303−0.24601.29420.061*
C40.2263 (2)−0.0699 (2)1.1318 (2)0.0467 (5)
H40.1795−0.07971.07060.056*
C50.3287 (2)0.0480 (2)1.0878 (2)0.0397 (4)
C60.3686 (2)0.1561 (2)0.9524 (2)0.0443 (5)
H60.32510.15230.88660.053*
C70.4694 (2)0.2659 (2)0.9156 (2)0.0436 (5)
H70.49350.33650.82580.052*
C80.5372 (2)0.2725 (2)1.0140 (2)0.0376 (4)
C90.39677 (19)0.0587 (2)1.1840 (2)0.0369 (4)
C100.6483 (2)0.3809 (2)0.9871 (2)0.0393 (4)
H100.68770.37111.05960.047*
C110.6986 (2)0.4928 (2)0.8682 (2)0.0431 (5)
H110.65990.50160.79560.052*
C120.8098 (2)0.6041 (2)0.8404 (2)0.0391 (4)
C130.8669 (2)0.6107 (2)0.9430 (2)0.0425 (5)
H130.83550.54191.03300.051*
C140.9701 (2)0.7191 (2)0.9123 (2)0.0461 (5)
H141.00760.72240.98190.055*
C151.0182 (2)0.8230 (2)0.7788 (2)0.0399 (4)
C160.9616 (2)0.8162 (2)0.6766 (2)0.0477 (5)
H160.99340.88470.58650.057*
C170.8583 (2)0.7086 (2)0.7072 (2)0.0495 (5)
H170.82050.70610.63750.059*
C181.1257 (2)0.9416 (2)0.7505 (2)0.0455 (5)
Cl10.59814 (7)0.30785 (6)0.33293 (5)0.0594 (2)
O1G0.3141 (2)0.2791 (2)0.5512 (3)0.1029 (8)
H1G0.38940.28740.49230.154*
C1G0.2941 (4)0.4036 (4)0.5760 (4)0.1012 (11)
H1G20.30730.48790.48860.121*
H1G30.36700.41340.61920.121*
C2G0.1559 (4)0.4111 (5)0.6627 (5)0.1184 (14)
H1G10.08470.42590.61200.178*
H2G10.15670.49280.69170.178*
H3G10.13400.31950.74220.178*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0750 (11)0.0517 (9)0.0382 (8)−0.0226 (8)−0.0202 (8)−0.0028 (6)
O20.0669 (10)0.0514 (9)0.0479 (9)−0.0268 (7)−0.0149 (8)−0.0029 (7)
O30.0867 (13)0.0795 (12)0.0550 (10)−0.0318 (10)−0.0257 (9)−0.0160 (9)
N10.0391 (9)0.0365 (8)0.0340 (9)−0.0044 (6)−0.0107 (7)−0.0107 (7)
C10.0451 (11)0.0391 (10)0.0423 (11)−0.0050 (8)−0.0097 (9)−0.0147 (9)
C20.0514 (12)0.0394 (10)0.0458 (12)−0.0106 (9)−0.0069 (10)−0.0089 (9)
C30.0465 (12)0.0426 (11)0.0620 (14)−0.0123 (9)−0.0104 (10)−0.0186 (10)
C40.0429 (11)0.0488 (11)0.0552 (13)−0.0033 (9)−0.0171 (10)−0.0232 (10)
C50.0368 (10)0.0375 (10)0.0440 (11)0.0018 (8)−0.0094 (9)−0.0152 (8)
C60.0444 (11)0.0506 (11)0.0417 (11)0.0014 (9)−0.0176 (9)−0.0173 (9)
C70.0462 (11)0.0449 (11)0.0349 (10)−0.0007 (9)−0.0119 (9)−0.0083 (8)
C80.0372 (10)0.0351 (9)0.0370 (10)0.0009 (8)−0.0068 (8)−0.0115 (8)
C90.0348 (10)0.0327 (9)0.0425 (11)−0.0020 (7)−0.0072 (8)−0.0145 (8)
C100.0403 (10)0.0372 (9)0.0369 (10)−0.0044 (8)−0.0094 (8)−0.0096 (8)
C110.0483 (11)0.0388 (10)0.0396 (11)−0.0030 (8)−0.0125 (9)−0.0103 (8)
C120.0425 (11)0.0331 (9)0.0370 (10)0.0004 (8)−0.0096 (8)−0.0085 (8)
C130.0463 (11)0.0387 (10)0.0331 (10)−0.0005 (8)−0.0095 (9)−0.0034 (8)
C140.0488 (12)0.0470 (11)0.0377 (11)−0.0033 (9)−0.0132 (9)−0.0086 (9)
C150.0387 (10)0.0348 (10)0.0401 (11)−0.0019 (8)−0.0077 (8)−0.0086 (8)
C160.0594 (13)0.0412 (10)0.0331 (10)−0.0135 (9)−0.0080 (9)−0.0039 (8)
C170.0622 (13)0.0466 (11)0.0363 (11)−0.0144 (10)−0.0146 (10)−0.0079 (9)
C180.0451 (11)0.0444 (11)0.0439 (12)−0.0060 (9)−0.0093 (9)−0.0133 (9)
Cl10.0853 (5)0.0497 (3)0.0408 (3)−0.0215 (3)−0.0166 (3)−0.0102 (2)
O1G0.0707 (13)0.0620 (12)0.160 (2)−0.0253 (10)0.0134 (13)−0.0484 (14)
C2G0.083 (2)0.107 (3)0.166 (4)−0.020 (2)−0.002 (2)−0.069 (3)
C1G0.125 (3)0.080 (2)0.099 (3)−0.030 (2)−0.002 (2)−0.0457 (19)
Geometric parameters (Å, º) top
O1—C11.349 (2)C10—C111.324 (3)
O1—H10.8200C10—H100.9300
O2—C181.314 (2)C11—C121.467 (3)
O2—H2A0.8200C11—H110.9300
O3—C181.201 (3)C12—C171.387 (3)
N1—C81.330 (2)C12—C131.389 (3)
N1—C91.372 (2)C13—C141.383 (3)
N1—H1A0.91 (2)C13—H130.9300
C1—C21.368 (3)C14—C151.387 (3)
C1—C91.404 (3)C14—H140.9300
C2—C31.391 (3)C15—C161.381 (3)
C2—H20.9300C15—C181.491 (3)
C3—C41.362 (3)C16—C171.378 (3)
C3—H30.9300C16—H160.9300
C4—C51.416 (3)C17—H170.9300
C4—H40.9300O1G—C1G1.327 (4)
C5—C91.408 (3)O1G—H1G0.8200
C5—C61.410 (3)C2G—C1G1.438 (5)
C6—C71.363 (3)C2G—H1G10.9600
C6—H60.9300C2G—H2G10.9600
C7—C81.413 (3)C2G—H3G10.9600
C7—H70.9300C1G—H1G20.9700
C8—C101.449 (3)C1G—H1G30.9700
C1—O1—H1109.5C10—C11—H11117.0
C18—O2—H2A109.5C12—C11—H11117.0
C8—N1—C9124.01 (17)C17—C12—C13118.51 (18)
C8—N1—H1A121.1 (13)C17—C12—C11119.03 (18)
C9—N1—H1A114.8 (13)C13—C12—C11122.45 (18)
O1—C1—C2125.27 (19)C14—C13—C12120.38 (18)
O1—C1—C9116.19 (16)C14—C13—H13119.8
C2—C1—C9118.54 (18)C12—C13—H13119.8
C1—C2—C3120.6 (2)C13—C14—C15120.72 (19)
C1—C2—H2119.7C13—C14—H14119.6
C3—C2—H2119.7C15—C14—H14119.6
C4—C3—C2122.17 (18)C16—C15—C14118.88 (18)
C4—C3—H3118.9C16—C15—C18121.90 (18)
C2—C3—H3118.9C14—C15—C18119.19 (18)
C3—C4—C5118.84 (19)C17—C16—C15120.46 (18)
C3—C4—H4120.6C17—C16—H16119.8
C5—C4—H4120.6C15—C16—H16119.8
C9—C5—C6117.21 (17)C16—C17—C12121.04 (19)
C9—C5—C4118.65 (18)C16—C17—H17119.5
C6—C5—C4124.13 (18)C12—C17—H17119.5
C7—C6—C5121.48 (18)O3—C18—O2123.57 (19)
C7—C6—H6119.3O3—C18—C15123.85 (19)
C5—C6—H6119.3O2—C18—C15112.58 (17)
C6—C7—C8119.97 (18)C1G—O1G—H1G109.5
C6—C7—H7120.0C1G—C2G—H1G1109.5
C8—C7—H7120.0C1G—C2G—H2G1109.5
N1—C8—C7118.15 (17)H1G1—C2G—H2G1109.5
N1—C8—C10116.55 (17)C1G—C2G—H3G1109.5
C7—C8—C10125.30 (18)H1G1—C2G—H3G1109.5
N1—C9—C1119.67 (17)H2G1—C2G—H3G1109.5
N1—C9—C5119.15 (17)O1G—C1G—C2G114.6 (3)
C1—C9—C5121.18 (17)O1G—C1G—H1G2108.6
C11—C10—C8125.54 (19)C2G—C1G—H1G2108.6
C11—C10—H10117.2O1G—C1G—H1G3108.6
C8—C10—H10117.2C2G—C1G—H1G3108.6
C10—C11—C12125.94 (19)H1G2—C1G—H1G3107.6
O1—C1—C2—C3179.5 (2)C6—C5—C9—C1−179.57 (18)
C9—C1—C2—C3−0.1 (3)C4—C5—C9—C1−0.1 (3)
C1—C2—C3—C40.0 (3)N1—C8—C10—C11−177.52 (19)
C2—C3—C4—C50.1 (3)C7—C8—C10—C112.8 (3)
C3—C4—C5—C9−0.1 (3)C8—C10—C11—C12179.21 (18)
C3—C4—C5—C6179.41 (19)C10—C11—C12—C17175.4 (2)
C9—C5—C6—C70.4 (3)C10—C11—C12—C13−5.7 (3)
C4—C5—C6—C7−179.11 (19)C17—C12—C13—C14−0.2 (3)
C5—C6—C7—C80.5 (3)C11—C12—C13—C14−179.04 (18)
C9—N1—C8—C71.6 (3)C12—C13—C14—C150.0 (3)
C9—N1—C8—C10−178.12 (16)C13—C14—C15—C16−0.2 (3)
C6—C7—C8—N1−1.4 (3)C13—C14—C15—C18177.77 (18)
C6—C7—C8—C10178.26 (18)C14—C15—C16—C170.4 (3)
C8—N1—C9—C1178.55 (17)C18—C15—C16—C17−177.4 (2)
C8—N1—C9—C5−0.8 (3)C15—C16—C17—C12−0.6 (3)
O1—C1—C9—N11.2 (3)C13—C12—C17—C160.5 (3)
C2—C1—C9—N1−179.14 (18)C11—C12—C17—C16179.4 (2)
O1—C1—C9—C5−179.47 (17)C16—C15—C18—O3−177.2 (2)
C2—C1—C9—C50.2 (3)C14—C15—C18—O35.0 (3)
C6—C5—C9—N1−0.3 (3)C16—C15—C18—O23.2 (3)
C4—C5—C9—N1179.25 (16)C14—C15—C18—O2−174.63 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.91 (2)2.27 (2)2.678 (2)107 (2)
O1—H1···Cl1i0.822.263.0780 (16)173
N1—H1A···Cl1ii0.91 (2)2.38 (2)3.2087 (18)151 (2)
O1G—H1G···Cl10.822.263.076 (3)179
O2—H2A···O1Giii0.821.852.634 (3)159
C4—H4···O3iv0.932.463.295 (3)150
C10—H10···Cl1ii0.932.693.446 (2)138
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y, z+1; (iii) x+1, y+1, z; (iv) x−1, y−1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.91 (2)2.27 (2)2.678 (2)107 (2)
O1—H1···Cl1i0.822.263.0780 (16)173
N1—H1A···Cl1ii0.91 (2)2.38 (2)3.2087 (18)151 (2)
O1G—H1G···Cl10.822.263.076 (3)179
O2—H2A···O1Giii0.821.852.634 (3)159
C4—H4···O3iv0.932.463.295 (3)150
C10—H10···Cl1ii0.932.693.446 (2)138
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y, z+1; (iii) x+1, y+1, z; (iv) x−1, y−1, z.
 

Acknowledgements

The authors thank the German Research Foundation within the priority programme Porous Metal-Organic Frameworks (SPP 1362, MOFs).

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ISSN: 2056-9890
Volume 69| Part 12| December 2013| Pages o1773-o1774
doi:10.1107/S1600536813030274
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