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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 71| Part 11| November 2015| Pages o850-o851
https://doi.org/10.1107/S2056989015019179

Crystal structure of morpholin-4-ium cinnamate

Graham Smitha*

aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
*Correspondence e-mail: g.smith@qut.edu.au

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 10 October 2015; accepted 11 October 2015; online 17 October 2015)

In the anhydrous salt formed from the reaction of morpholine with cinnamic acid, C4H10NO+·C9H7O2−, the acid side chain in the trans-cinnamate anion is significantly rotated out of the benzene plane [C—C—C— C torsion angle = 158.54 (17)°]. In the crystal, one of the the aminium H atoms is involved in an asymmetric three-centre cation–anion N—H⋯(O,O′) R12(4) hydrogen-bonding inter­action with the two carboxyl­ate O-atom acceptors of the anion. The second aminium-H atom forms an inter-species N—H⋯Ocarboxyl­ate hydrogen bond. The result of the hydrogen bonding is the formation of a chain structure extending along [100]. Chains are linked by C—H⋯O inter­actions, forming a supra­molecular layer parallel to (01-1).

CCDC reference: 1430629

Similar articles

1. Related literature

For background on morpholine compounds and the structure of an aliphatic morpholine salt, see: Kelley et al. (2013[Kelley, S. P., Narita, A., Holbrey, J. D., Green, K. D., Reichert, W. M. & Rogers, R. D. (2013). Cryst. Growth Des. 13, 965-975.]). For the structures of analogous morpholinate salts of some aromatic acid analogues, see: Chumakov et al. (2006[Chumakov, Y. M., Simonov, Y. A., Grosav, M., Crisan, M., Bocelli, G., Yakovenco, A. A. & Lyubetsky, D. (2006). Central Eur. J. Chem. 4, 458-475.]); Ishida et al. (2001a[Ishida, H., Rahman, B. & Kashino, S. (2001a). Acta Cryst. C57, 1450-1453.],b[Ishida, H., Rahman, B. & Kashino, S. (2001b). Acta Cryst. E57, o627-o629.],c[Ishida, H., Rahman, B. & Kashino, S. (2001c). Acta Cryst. E57, o630-o632.]); Smith & Lynch (2015[Smith, G. & Lynch, D. E. (2015). Acta Cryst. E71, 1392-1396.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C4H10NO+·C9H7O2−

  • Mr = 235.27

  • Triclinic, [P \overline 1]

  • a = 5.7365 (7) Å

  • b = 9.7526 (10) Å

  • c = 11.7760 (11) Å

  • α = 103.270 (8)°

  • β = 93.468 (9)°

  • γ = 105.493 (10)°

  • V = 612.69 (12) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 200 K

  • 0.52 × 0.24 × 0.05 mm

2.2. Data collection

  • Oxford Diffraction Gemini-S CCD-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.965, Tmax = 0.990

  • 4253 measured reflections

  • 2393 independent reflections

  • 1860 reflections with I > 2σ(I)

  • Rint = 0.023

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.100

  • S = 1.01

  • 2393 reflections

  • 160 parameters

  • 2 restraints

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

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1B—H11B⋯O14Ai 0.94 (2) 1.77 (2) 2.7052 (17) 170 (2)
N1B—H12B⋯O13A 0.94 (2) 1.73 (2) 2.6643 (17) 172 (2)
N1B—H12B⋯O14A 0.94 (2) 2.57 (2) 3.1868 (17) 123 (1)
C4A—H4A⋯O4Bii 0.95 2.46 3.393 (2) 167
C6B—H62B⋯O13Aiii 0.99 2.37 3.234 (2) 145
Symmetry codes: (i) x+1, y, z; (ii) x-2, y-1, z-1; (iii) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information

CCDC reference: 1430629

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015019179/tk5397sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019179/tk5397Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015019179/tk5397Isup3.cml

checkCIF report


Comment top

Morpholine (tetrahydro-2H-1,4-oxazine) forms salts with organic acids, and the crystal structures of a limited number of these with either aliphatic acids, e.g. the acetate (Kelley et al., 2013) or aromatic acids, e.g. the 4-nitrobenzoate (Chumakov et al., 2006), have been reported. With the salts of the aromatic acids, particularly those with non-associative substituent groups, cation–anion N—H···Ocarboxyl hydrogen-bonding interactions generate either one-dimensional chains or discrete cyclic heterotetrameric structures. In the present work, the title morpholinium salt of cinnamic acid, C4H10NO+ C9H7O2- was prepared and its structure is reported herein.

The asymmetric unit of the title salt comprises a morpholinium cation (B and a cinnamate anion (A), (Fig. 1). In the trans- cinnamate anion, the acid side chain is significantly rotated out of the benzene plane [defining torsion angle C6A—C1A—C11A— C12A = 158.54 (17)°]. In the crystal, a primary asymmetric three-centre R21(4) N1B—H···(O,O')carboxyl hydrogen-bonding interaction is present [N···O = 2.6643 (17) and 3.1868 (17) Å] (Table 1). The hydrogen-bonding extension involves the second aminium H atom of the cation to the carboxyl O14Ai acceptor of the anion, resulting in a one-dimensional ribbon structure extending along a (Fig. 2). Present also in the structure are minor weak inter-unit C—H···O interactions. C4A—H···O4Bii; C6B—H··· O13Aiii. No π–π interactions are present in the structure.

These ribbon structures are similar to those found in the morpholinium salt of one of the five isomeric chloro-nitrobenzoic acids (2,4-) (Ishida et al., 2001a). In the other four isomers [(2,5-), (4,3-), (4,2-), (5,2-)] (Ishida, 2001a, 2001b, 2001c), the cyclic heterotetrameric structures are found. However, among a set of four morpholinium salts of phenoxyacetic acid analogues (Smith & Lynch, 2015), there are four one-dimensional polymers and one cyclic heterotetramer.

Related literature top

For background on morpholine compounds and the structure of an aliphatic morpholine salt, see: Kelley et al. (2013). For the structures of analogous morpholinate salts of some aromatic acid analogues, see: Chumakov et al. (2006); Ishida et al. (2001a,b,c); Smith & Lynch (2015).

Experimental top

The title compound was prepared by the dropwise addition of morpholine at room temperature to a solution of cinnamic acid (150 mg) in ethanol (10 ml). Room temperature evaporation of the solution gave an oil which was redissolved in ethanol, finally giving thin colourless plates of the title compound from which a specimen was cleaved for the X-ray analysis.

Refinement top

Hydrogen atoms were placed in calculated positions [C—Haromatic = 0.95 Å or C—Hmethylene = 0.99 Å] and were allowed to ride in the refinements, with Uiso(H) = 1.2Ueq(C). The aminium H atoms were located in a difference-Fourier analysis and were allowed to refine with distance restraints [d(N—H) = 0.92 (2) Å and Uiso(H) = 1.2Ueq(N)

Structure description top

Morpholine (tetrahydro-2H-1,4-oxazine) forms salts with organic acids, and the crystal structures of a limited number of these with either aliphatic acids, e.g. the acetate (Kelley et al., 2013) or aromatic acids, e.g. the 4-nitrobenzoate (Chumakov et al., 2006), have been reported. With the salts of the aromatic acids, particularly those with non-associative substituent groups, cation–anion N—H···Ocarboxyl hydrogen-bonding interactions generate either one-dimensional chains or discrete cyclic heterotetrameric structures. In the present work, the title morpholinium salt of cinnamic acid, C4H10NO+ C9H7O2- was prepared and its structure is reported herein.

The asymmetric unit of the title salt comprises a morpholinium cation (B and a cinnamate anion (A), (Fig. 1). In the trans- cinnamate anion, the acid side chain is significantly rotated out of the benzene plane [defining torsion angle C6A—C1A—C11A— C12A = 158.54 (17)°]. In the crystal, a primary asymmetric three-centre R21(4) N1B—H···(O,O')carboxyl hydrogen-bonding interaction is present [N···O = 2.6643 (17) and 3.1868 (17) Å] (Table 1). The hydrogen-bonding extension involves the second aminium H atom of the cation to the carboxyl O14Ai acceptor of the anion, resulting in a one-dimensional ribbon structure extending along a (Fig. 2). Present also in the structure are minor weak inter-unit C—H···O interactions. C4A—H···O4Bii; C6B—H··· O13Aiii. No π–π interactions are present in the structure.

These ribbon structures are similar to those found in the morpholinium salt of one of the five isomeric chloro-nitrobenzoic acids (2,4-) (Ishida et al., 2001a). In the other four isomers [(2,5-), (4,3-), (4,2-), (5,2-)] (Ishida, 2001a, 2001b, 2001c), the cyclic heterotetrameric structures are found. However, among a set of four morpholinium salts of phenoxyacetic acid analogues (Smith & Lynch, 2015), there are four one-dimensional polymers and one cyclic heterotetramer.

For background on morpholine compounds and the structure of an aliphatic morpholine salt, see: Kelley et al. (2013). For the structures of analogous morpholinate salts of some aromatic acid analogues, see: Chumakov et al. (2006); Ishida et al. (2001a,b,c); Smith & Lynch (2015).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The atom-numbering scheme and the molecular conformation of the morpholinium anion (B) and the cinnamate cation (A) in the title salt, with displacement ellipsoids drawn at the 40% probability level. The cation–anion hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. The one-dimensional hydrogen-bonded polymeric structure extending along a. For symmetry codes, see Table 1.
Morpholin-4-ium 3-phenylprop-2-enoate top
Crystal data top
C4H10NO+·C9H7O2−Z = 2
Mr = 235.27F(000) = 252
Triclinic, P1Dx = 1.281 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7365 (7) ÅCell parameters from 1133 reflections
b = 9.7526 (10) Åθ = 3.6–28.4°
c = 11.7760 (11) ŵ = 0.09 mm−1
α = 103.270 (8)°T = 200 K
β = 93.468 (9)°Plate, colourless
γ = 105.493 (10)°0.52 × 0.24 × 0.05 mm
V = 612.69 (12) Å3
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer		2393 independent reflections
Radiation source: Enhance (Mo) X-ray source1860 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 16.077 pixels mm-1θmax = 26.0°, θmin = 3.2°
ω scansh = −6→7
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)		k = −12→12
Tmin = 0.965, Tmax = 0.990l = −14→14
4253 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0429P)2 + 0.0676P]
where P = (Fo2 + 2Fc2)/3
2393 reflections(Δ/σ)max < 0.001
160 parametersΔρmax = 0.15 e Å−3
2 restraintsΔρmin = −0.15 e Å−3
Crystal data top
C4H10NO+·C9H7O2−γ = 105.493 (10)°
Mr = 235.27V = 612.69 (12) Å3
Triclinic, P1Z = 2
a = 5.7365 (7) ÅMo Kα radiation
b = 9.7526 (10) ŵ = 0.09 mm−1
c = 11.7760 (11) ÅT = 200 K
α = 103.270 (8)°0.52 × 0.24 × 0.05 mm
β = 93.468 (9)°
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer		2393 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)		1860 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.990Rint = 0.023
4253 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0432 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.15 e Å−3
2393 reflectionsΔρmin = −0.15 e Å−3
160 parameters
Special details top

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 esds 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 > 2sigma(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
O13A0.72059 (18)0.32720 (13)0.51574 (9)0.0370 (4)
O14A0.50422 (18)0.43517 (12)0.63746 (10)0.0323 (4)
C1A0.0669 (3)0.04440 (16)0.29775 (13)0.0256 (5)
C2A−0.1554 (3)0.00183 (17)0.34093 (15)0.0299 (5)
C3A−0.3583 (3)−0.09424 (18)0.26731 (16)0.0365 (6)
C4A−0.3450 (3)−0.14842 (18)0.14947 (16)0.0388 (6)
C5A−0.1258 (3)−0.10770 (18)0.10580 (15)0.0384 (6)
C6A0.0789 (3)−0.01381 (17)0.17959 (14)0.0321 (5)
C11A0.2852 (3)0.14762 (17)0.37395 (14)0.0262 (5)
C12A0.2907 (3)0.24300 (17)0.47379 (14)0.0276 (5)
C13A0.5213 (3)0.34254 (17)0.54714 (13)0.0258 (5)
O4B1.2058 (2)0.63511 (13)0.93100 (10)0.0398 (4)
N1B1.0764 (2)0.48489 (14)0.68969 (11)0.0253 (4)
C2B1.0246 (3)0.40701 (18)0.78354 (14)0.0310 (5)
C3B1.2089 (3)0.48633 (18)0.89057 (14)0.0354 (6)
C5B1.2676 (3)0.71057 (18)0.84191 (15)0.0355 (6)
C6B1.0875 (3)0.64183 (17)0.73241 (14)0.0298 (5)
H2A−0.167200.039300.421600.0360*
H3A−0.50810−0.123300.297900.0440*
H4A−0.48570−0.213200.098800.0470*
H5A−0.11570−0.144400.024800.0460*
H6A0.229900.011300.149200.0390*
H11A0.438200.145100.348300.0310*
H12A0.140000.248900.500700.0330*
H11B1.227 (3)0.4752 (17)0.6663 (13)0.0300*
H12B0.951 (3)0.4376 (17)0.6261 (12)0.0300*
H21B1.032300.304700.755500.0370*
H22B0.858300.403300.803700.0370*
H31B1.172100.435400.953900.0420*
H32B1.373700.484300.871200.0420*
H51B1.432500.708300.822900.0430*
H52B1.271300.814800.871600.0430*
H61B0.924300.650200.749500.0360*
H62B1.137700.694000.671000.0360*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O13A0.0181 (6)0.0508 (8)0.0320 (7)0.0093 (5)−0.0013 (5)−0.0075 (6)
O14A0.0217 (6)0.0368 (7)0.0304 (6)0.0073 (5)−0.0001 (5)−0.0048 (5)
C1A0.0255 (8)0.0211 (8)0.0289 (9)0.0061 (7)−0.0022 (7)0.0063 (7)
C2A0.0265 (8)0.0251 (9)0.0334 (9)0.0043 (7)−0.0008 (7)0.0035 (7)
C3A0.0259 (9)0.0273 (9)0.0516 (12)0.0036 (7)−0.0029 (8)0.0075 (8)
C4A0.0375 (10)0.0242 (9)0.0453 (11)0.0036 (8)−0.0174 (8)0.0026 (8)
C5A0.0522 (11)0.0299 (10)0.0279 (9)0.0099 (9)−0.0062 (8)0.0026 (8)
C6A0.0349 (9)0.0279 (9)0.0312 (9)0.0069 (8)0.0013 (7)0.0065 (7)
C11A0.0213 (8)0.0277 (9)0.0294 (9)0.0065 (7)0.0021 (6)0.0080 (7)
C12A0.0191 (8)0.0311 (9)0.0303 (9)0.0072 (7)0.0019 (6)0.0039 (7)
C13A0.0213 (8)0.0295 (9)0.0261 (9)0.0076 (7)0.0007 (6)0.0064 (7)
O4B0.0518 (8)0.0356 (7)0.0241 (6)0.0068 (6)−0.0002 (5)0.0001 (5)
N1B0.0185 (6)0.0305 (8)0.0222 (7)0.0066 (6)−0.0013 (5)−0.0007 (6)
C2B0.0287 (8)0.0269 (9)0.0361 (10)0.0057 (7)0.0024 (7)0.0085 (8)
C3B0.0402 (10)0.0363 (10)0.0286 (9)0.0101 (8)−0.0011 (7)0.0088 (8)
C5B0.0380 (10)0.0257 (9)0.0351 (10)0.0009 (8)0.0011 (8)0.0032 (8)
C6B0.0296 (9)0.0280 (9)0.0321 (9)0.0082 (7)0.0045 (7)0.0085 (7)
Geometric parameters (Å, º) top
O13A—C13A1.258 (2)C2A—H2A0.9500
O14A—C13A1.2553 (19)C3A—H3A0.9500
O4B—C3B1.425 (2)C4A—H4A0.9500
O4B—C5B1.424 (2)C5A—H5A0.9500
N1B—C2B1.480 (2)C6A—H6A0.9500
N1B—C6B1.480 (2)C11A—H11A0.9500
N1B—H11B0.944 (18)C12A—H12A0.9500
N1B—H12B0.943 (15)C2B—C3B1.503 (2)
C1A—C6A1.390 (2)C5B—C6B1.501 (2)
C1A—C2A1.396 (2)C2B—H21B0.9900
C1A—C11A1.471 (2)C2B—H22B0.9900
C2A—C3A1.381 (2)C3B—H31B0.9900
C3A—C4A1.382 (3)C3B—H32B0.9900
C4A—C5A1.382 (3)C5B—H51B0.9900
C5A—C6A1.382 (2)C5B—H52B0.9900
C11A—C12A1.314 (2)C6B—H61B0.9900
C12A—C13A1.493 (2)C6B—H62B0.9900
C3B—O4B—C5B109.75 (12)C1A—C6A—H6A120.00
C2B—N1B—C6B111.05 (12)C12A—C11A—H11A117.00
C6B—N1B—H11B110.9 (10)C1A—C11A—H11A117.00
C2B—N1B—H12B107.7 (10)C11A—C12A—H12A118.00
H11B—N1B—H12B109.8 (14)C13A—C12A—H12A118.00
C2B—N1B—H11B107.0 (10)N1B—C2B—C3B109.50 (14)
C6B—N1B—H12B110.3 (10)O4B—C3B—C2B110.91 (14)
C2A—C1A—C11A121.67 (14)O4B—C5B—C6B111.36 (14)
C6A—C1A—C11A120.00 (15)N1B—C6B—C5B109.46 (14)
C2A—C1A—C6A118.33 (15)N1B—C2B—H21B110.00
C1A—C2A—C3A120.55 (16)N1B—C2B—H22B110.00
C2A—C3A—C4A120.46 (17)C3B—C2B—H21B110.00
C3A—C4A—C5A119.55 (16)C3B—C2B—H22B110.00
C4A—C5A—C6A120.21 (16)H21B—C2B—H22B108.00
C1A—C6A—C5A120.88 (16)O4B—C3B—H31B109.00
C1A—C11A—C12A126.79 (16)O4B—C3B—H32B109.00
C11A—C12A—C13A123.45 (16)C2B—C3B—H31B109.00
O13A—C13A—O14A123.98 (15)C2B—C3B—H32B109.00
O13A—C13A—C12A118.14 (14)H31B—C3B—H32B108.00
O14A—C13A—C12A117.87 (15)O4B—C5B—H51B109.00
C1A—C2A—H2A120.00O4B—C5B—H52B109.00
C3A—C2A—H2A120.00C6B—C5B—H51B109.00
C4A—C3A—H3A120.00C6B—C5B—H52B109.00
C2A—C3A—H3A120.00H51B—C5B—H52B108.00
C3A—C4A—H4A120.00N1B—C6B—H61B110.00
C5A—C4A—H4A120.00N1B—C6B—H62B110.00
C6A—C5A—H5A120.00C5B—C6B—H61B110.00
C4A—C5A—H5A120.00C5B—C6B—H62B110.00
C5A—C6A—H6A120.00H61B—C6B—H62B108.00
C3B—O4B—C5B—C6B61.19 (17)C1A—C2A—C3A—C4A−0.7 (3)
C5B—O4B—C3B—C2B−61.29 (17)C2A—C3A—C4A—C5A1.0 (3)
C2B—N1B—C6B—C5B54.09 (17)C3A—C4A—C5A—C6A0.2 (3)
C6B—N1B—C2B—C3B−54.46 (17)C4A—C5A—C6A—C1A−1.8 (3)
C2A—C1A—C6A—C5A2.1 (2)C1A—C11A—C12A—C13A178.94 (15)
C6A—C1A—C11A—C12A158.54 (17)C11A—C12A—C13A—O13A−5.0 (2)
C11A—C1A—C6A—C5A−178.16 (16)C11A—C12A—C13A—O14A175.97 (16)
C2A—C1A—C11A—C12A−21.7 (3)N1B—C2B—C3B—O4B57.95 (17)
C6A—C1A—C2A—C3A−0.8 (2)O4B—C5B—C6B—N1B−57.43 (18)
C11A—C1A—C2A—C3A179.41 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1B—H11B···O14Ai0.94 (2)1.77 (2)2.7052 (17)170 (2)
N1B—H12B···O13A0.94 (2)1.73 (2)2.6643 (17)172 (2)
N1B—H12B···O14A0.94 (2)2.57 (2)3.1868 (17)123 (1)
C4A—H4A···O4Bii0.952.463.393 (2)167
C11A—H11A···O13A0.952.482.812 (2)101
C6B—H62B···O13Aiii0.992.373.234 (2)145
Symmetry codes: (i) x+1, y, z; (ii) x−2, y−1, z−1; (iii) −x+2, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1B—H11B···O14Ai0.944 (18)1.770 (18)2.7052 (17)170.2 (15)
N1B—H12B···O13A0.943 (15)1.728 (16)2.6643 (17)171.5 (15)
N1B—H12B···O14A0.943 (15)2.569 (18)3.1868 (17)123.4 (12)
C4A—H4A···O4Bii0.952.463.393 (2)167
C6B—H62B···O13Aiii0.992.373.234 (2)145
Symmetry codes: (i) x+1, y, z; (ii) x−2, y−1, z−1; (iii) −x+2, −y+1, −z+1.
 

Acknowledgements

GS acknowledges financial support from the Science and Engineering Faculty and the University Library, Queensland University of Technology.

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ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o850-o851
https://doi.org/10.1107/S2056989015019179
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