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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 12| December 2015| Pages o1063-o1064
https://doi.org/10.1107/S2056989015023853

Crystal structure of (1Z,2E)-cinnamaldehyde oxime

Bernhard Bugenhagen,a Nuha Al Soom,b Yosef Al Jasemc and Thies Thiemannb*

aInstitute of Inorganic Chemistry, University of Hamburg, Hamburg, Germany, bDepartment of Chemistry, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates, and cDepartment of Chemical Engineering, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates
*Correspondence e-mail: thies@uaeu.ac.ae

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 December 2015; accepted 11 December 2015; online 16 December 2015)

The title compound, C9H9NO, crystallized with two independent mol­ecules (A and B) in the asymmetric unit. The conformation of the two mol­ecules differs slightly with the phenyl ring in mol­ecule A, forming a dihedral angle of 15.38 (12)° with the oxime group (O—N=C), compared to the corresponding angle of 26.29 (11)° in mol­ecule B. In the crystal, the A and B mol­ecules are linked head-to-head by O—H⋯N hydrogen bonds, forming –A–B–A–B– zigzag chains along [010]. Within the chains and between neighbouring chains there are C—H⋯π inter­actions present, forming a three-dimensional structure.

CCDC reference: 1441984

Similar articles

1. Related literature

For the other methods of preparation of the title compound, see: Mirjafari et al. (2011[Mirjafari, A., Mobarrez, N., O'Brien, R. A., Davis, J. H. Jr & Noei, J. (2011). C. R. Chim. 14, 1065-1070.]); Kitahara et al. (2008[Kitahara, K., Toma, T., Shimokawa, J. & Fukuyama, T. (2008). Org. Lett. 10, 2259-2261.]). For the uses of a such compound, see: Narsaiah & Nagaiah (2004[Narsaiah, A. V. & Nagaiah, K. (2004). Adv. Synth. Catal. 346, 1271-1274.]); Jasem et al. (2014[Jasem, Y. A., Barkhad, M., Khazali, M. A., Butt, H. P., El-Khwass, N. A., Alazani, M., Hindawi, B., & Thiemann, T. (2014). J. Chem. Res. (S), 38, 80-84.]); Garton et al. (2010[Garton, N., Bailey, N., Bamford, M., Demont, E., Farre-Gutierrez, I., Hutley, G., Bravi, G. & Pickering, P. (2010). Bioorg. Med. Chem. Lett. 20, 1049-1054.]); Patil et al. (2012[Patil, U. B., Kumthekar, K. R. & Nagarkar, J. M. (2012). Tetrahedron Lett. 53, 3706-3709.]); Kaur et al. (2006[Kaur, J., Singh, B. & Singal, K. K. (2006). Chem. Heterocycl. Compd. 42, 818-822.]); Boruah & Konwar (2012[Boruah, M. & Konwar, D. (2012). Synth. Commun. 42, 3261-3268.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C9H9NO

  • Mr = 147.17

  • Orthorhombic, P b c a

  • a = 10.231 (5) Å

  • b = 7.584 (3) Å

  • c = 41.816 (18) Å

  • V = 3245 (2) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.2 × 0.2 × 0.1 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.666, Tmax = 0.746

  • 34431 measured reflections

  • 3944 independent reflections

  • 3724 reflections with I > 2σ(I)

  • Rint = 0.022

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.113

  • S = 1.10

  • 3944 reflections

  • 207 parameters

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

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C1A–C6A and C1B–C6B, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1A—H1A⋯N1Bi 0.91 (2) 1.85 (2) 2.755 (2) 174 (2)
O1B—H1B⋯N1Aii 0.92 (2) 1.95 (2) 2.853 (2) 170 (2)
C2A—H2A⋯Cg1iii 0.95 2.70 3.563 (2) 151
C5B—H5B⋯Cg2iv 0.95 2.80 3.508 (2) 132
C9B—H9B⋯Cg2v 0.95 2.82 3.717 (2) 159
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]; (iv) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). 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: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information

CCDC reference: 1441984

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023853/su5260sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023853/su5260Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015023853/su5260Isup3.cml

checkCIF report


Structural commentary top

Many uses of cinnamaldehyde oxime have been reported, such as the conversion to cinnamo­nitrile (Narsaiah & Nagaiah 2004; Jasem et al. 2014), conversion to cinnamide (Garton et al. 2010), and as a starting material for N-heterocycles: tetra­zole (Patil et al. 2012), isoxazoline (Kaur et al. 2006), and izoxazoline (Boruah & Konwar 2012).

The title compound, crystallized with two independent molecules A and B in the asymmetric unit (Fig. 1). The aromatic ring in molecule A (C1A—C6A) forms a dihedral angle of 15.38 (12)° with the oxime group (C9A/N1A/O1A), compared to a corresponding angle of 26.29 (11)° in molecule B. This conformational difference between molecules A and B is due to bond rotation, not only about bonds (C1—C7) and (C8—C9) but also of that of (C7—C8), where in molecule A the torsion angle C1—C7—C8—C9 is -174.32 (11)° while in molecule B the corresponding angle is -179.24 (11) °. The bond lengths, C7—C8, of molecules A and B are similar.

In the crystal, the A molecules align opposite B molecules, and they are linked via O—H···N hydrogen bonds forming -A—B—A—B- zigzag chains propagating along the b axis (Table 1 and Fig. 2). Adjacent molecules of the same type are tilted against each other, with the aromatic rings (C1—C6) being inclined to one another by 77.64 (2) and 59.04 (2)° for molecules A and B, respectively. In addition, adjacent molecules of the same type exhibit weak C—H..π (C2A—H2A···Cg1 and C5B—H5B···Cg2) contacts along the b axis direction (Table 1 and Fig. 2). Along the c axis, inversion related dimers stack with an offset of 11.47 (2) Å and connected via a weak C—H..π (C9B—H9B···Cg2) contact (Fig. 3 and Table 1).

Synthesis and crystallization top

To a solution of cinnamaldehyde (1.32 g, 10 mmol) in ethanol (20 ml) was added drop wise a solution of hydroxyl­amine hydro­chloride (2.74 g, 39.7 mmol) in water (7.5 ml), and the resulting mixture was stirred at 60 oC for 3 h. Thereafter, about half of the solvent was removed in vacuo, and the remaining reaction mixture was poured into water (50 ml) and extracted with CHCl3 (3 × 20 ml). The combined organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was subjected to column chromatography (eluant: CH2Cl2) to yield the title compound as colourless needles (yield: 956 mg, 65%; m.p. 348 – 349 K). IR (νmax, KBr, cm-1) 3356, 1630, 1444, 1291, 987, 976, 955, 747, 691; 1H NMR (400 MHz, CDCl3, δH) 6.84 (1H, d, 3J = 5.6 Hz), 7.28 – 7.55 (6H, m), 7.94 (1H, t, 3J = 4.8 Hz); δC (100.5 MHz, CDCl3) 121.5 (CH), 127.0 (2C, CH), 128.8 (2C, CH), 129.0 (CH), 135.7 (Cquat), 139.2 (CH), 152.0 (CH). Crystals for X-ray analysis were grown from a solution in CH2Cl2/hexane (1:1, v/v) by slow evaporation of the solvents.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The OH H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were fixed geometrically (C—H = 0.95 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).

Related literature top

For the other methods of preparation of the title compound, see: Mirjafari et al. (2011); Kitahara et al. (2008). For the uses of a such compound, see: Narsaiah & Nagaiah (2004); Jasem et al. (2014); Garton et al. (2010); Patil et al. (2012); Kaur et al. (2006); Boruah & Konwar (2012).

Structure description top

Many uses of cinnamaldehyde oxime have been reported, such as the conversion to cinnamo­nitrile (Narsaiah & Nagaiah 2004; Jasem et al. 2014), conversion to cinnamide (Garton et al. 2010), and as a starting material for N-heterocycles: tetra­zole (Patil et al. 2012), isoxazoline (Kaur et al. 2006), and izoxazoline (Boruah & Konwar 2012).

The title compound, crystallized with two independent molecules A and B in the asymmetric unit (Fig. 1). The aromatic ring in molecule A (C1A—C6A) forms a dihedral angle of 15.38 (12)° with the oxime group (C9A/N1A/O1A), compared to a corresponding angle of 26.29 (11)° in molecule B. This conformational difference between molecules A and B is due to bond rotation, not only about bonds (C1—C7) and (C8—C9) but also of that of (C7—C8), where in molecule A the torsion angle C1—C7—C8—C9 is -174.32 (11)° while in molecule B the corresponding angle is -179.24 (11) °. The bond lengths, C7—C8, of molecules A and B are similar.

In the crystal, the A molecules align opposite B molecules, and they are linked via O—H···N hydrogen bonds forming -A—B—A—B- zigzag chains propagating along the b axis (Table 1 and Fig. 2). Adjacent molecules of the same type are tilted against each other, with the aromatic rings (C1—C6) being inclined to one another by 77.64 (2) and 59.04 (2)° for molecules A and B, respectively. In addition, adjacent molecules of the same type exhibit weak C—H..π (C2A—H2A···Cg1 and C5B—H5B···Cg2) contacts along the b axis direction (Table 1 and Fig. 2). Along the c axis, inversion related dimers stack with an offset of 11.47 (2) Å and connected via a weak C—H..π (C9B—H9B···Cg2) contact (Fig. 3 and Table 1).

For the other methods of preparation of the title compound, see: Mirjafari et al. (2011); Kitahara et al. (2008). For the uses of a such compound, see: Narsaiah & Nagaiah (2004); Jasem et al. (2014); Garton et al. (2010); Patil et al. (2012); Kaur et al. (2006); Boruah & Konwar (2012).

Synthesis and crystallization top

To a solution of cinnamaldehyde (1.32 g, 10 mmol) in ethanol (20 ml) was added drop wise a solution of hydroxyl­amine hydro­chloride (2.74 g, 39.7 mmol) in water (7.5 ml), and the resulting mixture was stirred at 60 oC for 3 h. Thereafter, about half of the solvent was removed in vacuo, and the remaining reaction mixture was poured into water (50 ml) and extracted with CHCl3 (3 × 20 ml). The combined organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was subjected to column chromatography (eluant: CH2Cl2) to yield the title compound as colourless needles (yield: 956 mg, 65%; m.p. 348 – 349 K). IR (νmax, KBr, cm-1) 3356, 1630, 1444, 1291, 987, 976, 955, 747, 691; 1H NMR (400 MHz, CDCl3, δH) 6.84 (1H, d, 3J = 5.6 Hz), 7.28 – 7.55 (6H, m), 7.94 (1H, t, 3J = 4.8 Hz); δC (100.5 MHz, CDCl3) 121.5 (CH), 127.0 (2C, CH), 128.8 (2C, CH), 129.0 (CH), 135.7 (Cquat), 139.2 (CH), 152.0 (CH). Crystals for X-ray analysis were grown from a solution in CH2Cl2/hexane (1:1, v/v) by slow evaporation of the solvents.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The OH H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were fixed geometrically (C—H = 0.95 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the two independent molecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial view along the a axis of the crystal packing of the title compound. The O—H···N hydrogen bonds, and the C—H···π contacts between adjacent molecules are shown as dashed lines (see Table 1).
[Figure 3] Fig. 3. A view along the b axis of three stacked molecular motifs made of A (blue) and B (green) interconnected molecules forming chains along the b axis. The hydrogen bonds and C—H···π interactions are shown as dashed lines (see Table 1).
(1Z,2E)-3-phenylprop-2-enal oxime top
Crystal data top
C9H9NODx = 1.205 Mg m−3
Mr = 147.17Melting point: 348 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 10.231 (5) ÅCell parameters from 9623 reflections
b = 7.584 (3) Åθ = 2.2–28.4°
c = 41.816 (18) ŵ = 0.08 mm−1
V = 3245 (2) Å3T = 100 K
Z = 16Block, colourless
F(000) = 12480.2 × 0.2 × 0.1 mm
Data collection top
Bruker APEXII CCD
diffractometer		3724 reflections with I > 2σ(I)
φ and ω scansRint = 0.022
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		θmax = 28.6°, θmin = 1.0°
Tmin = 0.666, Tmax = 0.746h = −13→13
34431 measured reflectionsk = −10→10
3944 independent reflectionsl = −55→53
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0445P)2 + 2.1543P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
3944 reflectionsΔρmax = 0.45 e Å−3
207 parametersΔρmin = −0.19 e Å−3
Crystal data top
C9H9NOV = 3245 (2) Å3
Mr = 147.17Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 10.231 (5) ŵ = 0.08 mm−1
b = 7.584 (3) ÅT = 100 K
c = 41.816 (18) Å0.2 × 0.2 × 0.1 mm
Data collection top
Bruker APEXII CCD
diffractometer		3944 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		3724 reflections with I > 2σ(I)
Tmin = 0.666, Tmax = 0.746Rint = 0.022
34431 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.45 e Å−3
3944 reflectionsΔρmin = −0.19 e Å−3
207 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1B0.27939 (9)0.14918 (13)0.83349 (2)0.0214 (2)
O1A0.57897 (9)0.36622 (12)0.60376 (2)0.0210 (2)
N1A0.65418 (10)0.21056 (14)0.60658 (2)0.0172 (2)
N1B0.37727 (11)0.02042 (14)0.83755 (2)0.0189 (2)
C9A0.66426 (11)0.12592 (16)0.57973 (3)0.0162 (2)
H9A0.70960.01670.58040.019*
C7A0.65649 (11)0.10018 (15)0.52143 (3)0.0146 (2)
H7A0.71350.00240.52420.017*
C1A0.62383 (11)0.14952 (15)0.48805 (3)0.0137 (2)
C6A0.52038 (11)0.26618 (15)0.48030 (3)0.0152 (2)
H6A0.46650.31240.49680.018*
C2B0.50012 (12)−0.04774 (16)0.69394 (3)0.0171 (2)
H2B0.5770−0.11140.69930.021*
C5A0.49730 (12)0.31367 (16)0.44838 (3)0.0182 (2)
H5A0.42780.39200.44340.022*
C7B0.44406 (12)−0.04211 (15)0.75192 (3)0.0167 (2)
H7B0.5154−0.12020.75520.020*
C2A0.70079 (12)0.08011 (17)0.46297 (3)0.0189 (2)
H2A0.7689−0.00080.46780.023*
C8A0.61346 (11)0.18013 (15)0.54843 (3)0.0152 (2)
H8A0.55020.27160.54710.018*
C1B0.41218 (11)0.00325 (15)0.71837 (3)0.0153 (2)
C3B0.47534 (13)−0.00548 (17)0.66187 (3)0.0202 (3)
H3B0.5352−0.04080.64570.024*
C5B0.27317 (13)0.13917 (17)0.67760 (3)0.0224 (3)
H5B0.19630.20230.67200.027*
C6B0.29760 (12)0.09644 (16)0.70966 (3)0.0188 (2)
H6B0.23680.13030.72570.023*
C4B0.36242 (14)0.08882 (17)0.65358 (3)0.0228 (3)
H4B0.34610.11860.63190.027*
C8B0.38138 (12)0.01692 (16)0.77854 (3)0.0170 (2)
H8B0.30880.09420.77630.020*
C9B0.42381 (13)−0.03653 (16)0.81057 (3)0.0191 (2)
H9B0.4921−0.12120.81170.023*
C4A0.57625 (13)0.24623 (18)0.42372 (3)0.0220 (3)
H4A0.56070.27990.40220.026*
C3A0.67797 (14)0.12902 (18)0.43106 (3)0.0235 (3)
H3A0.73140.08280.41450.028*
H1B0.248 (2)0.163 (2)0.8539 (4)0.039 (5)*
H1A0.588 (2)0.415 (3)0.6235 (5)0.048 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1B0.0216 (4)0.0283 (5)0.0144 (4)0.0041 (4)0.0037 (3)0.0011 (3)
O1A0.0301 (5)0.0197 (4)0.0131 (4)0.0029 (4)−0.0024 (3)−0.0010 (3)
N1A0.0181 (5)0.0191 (5)0.0144 (5)−0.0022 (4)−0.0008 (4)0.0040 (4)
N1B0.0237 (5)0.0183 (5)0.0146 (5)−0.0013 (4)−0.0001 (4)0.0023 (4)
C9A0.0169 (5)0.0174 (5)0.0141 (5)−0.0026 (4)−0.0012 (4)0.0033 (4)
C7A0.0143 (5)0.0136 (5)0.0159 (5)−0.0011 (4)−0.0030 (4)0.0012 (4)
C1A0.0158 (5)0.0118 (5)0.0134 (5)−0.0026 (4)−0.0024 (4)−0.0012 (4)
C6A0.0148 (5)0.0147 (5)0.0160 (5)−0.0010 (4)−0.0008 (4)−0.0011 (4)
C2B0.0167 (5)0.0167 (5)0.0178 (5)−0.0018 (4)0.0025 (4)−0.0009 (4)
C5A0.0179 (5)0.0171 (5)0.0195 (6)−0.0008 (4)−0.0054 (4)0.0022 (4)
C7B0.0196 (5)0.0142 (5)0.0164 (5)0.0014 (4)0.0010 (4)0.0006 (4)
C2A0.0206 (6)0.0189 (6)0.0172 (6)0.0051 (5)−0.0019 (4)−0.0028 (4)
C8A0.0164 (5)0.0151 (5)0.0141 (5)−0.0020 (4)−0.0023 (4)0.0015 (4)
C1B0.0189 (5)0.0125 (5)0.0144 (5)−0.0018 (4)0.0019 (4)−0.0005 (4)
C3B0.0254 (6)0.0203 (6)0.0149 (5)−0.0065 (5)0.0053 (5)−0.0020 (4)
C5B0.0265 (7)0.0189 (6)0.0218 (6)0.0021 (5)−0.0048 (5)0.0013 (5)
C6B0.0211 (6)0.0179 (6)0.0175 (6)0.0020 (5)0.0019 (4)−0.0010 (4)
C4B0.0324 (7)0.0207 (6)0.0152 (5)−0.0065 (5)−0.0032 (5)0.0023 (5)
C8B0.0206 (5)0.0157 (5)0.0146 (5)−0.0005 (4)0.0015 (4)0.0009 (4)
C9B0.0239 (6)0.0171 (6)0.0162 (5)0.0001 (5)0.0007 (4)0.0022 (4)
C4A0.0290 (6)0.0236 (6)0.0133 (5)−0.0014 (5)−0.0052 (5)0.0011 (5)
C3A0.0299 (7)0.0270 (7)0.0137 (5)0.0033 (5)0.0015 (5)−0.0048 (5)
Geometric parameters (Å, º) top
C1A—C2A1.4133 (17)C6A—H6A0.9500
C1A—C6A1.4171 (16)C6B—H6B0.9500
C1B—C6B1.4166 (17)C7A—C8A1.3548 (17)
C2A—C3A1.4043 (18)C7A—C1A1.4834 (16)
C2A—H2A0.9500C7A—H7A0.9500
C2B—C3B1.4020 (17)C7B—C8B1.3606 (17)
C2B—C1B1.4152 (16)C7B—C1B1.4806 (17)
C2B—H2B0.9500C7B—H7B0.9500
C3A—H3A0.9500C8A—H8A0.9500
C3B—C4B1.402 (2)C8B—C9B1.4649 (17)
C3B—H3B0.9500C8B—H8B0.9500
C4A—C3A1.4027 (19)C9A—C8A1.4671 (16)
C4A—H4A0.9500C9A—H9A0.9500
C4B—H4B0.9500C9B—H9B0.9500
C5A—C4A1.4063 (19)N1A—C9A1.2977 (16)
C5A—H5A0.9500N1B—C9B1.2985 (16)
C5B—C4B1.4100 (19)O1A—H1A0.91 (2)
C5B—C6B1.4017 (18)O1A—N1A1.4141 (14)
C5B—H5B0.9500O1B—H1B0.917 (19)
C6A—C5A1.4026 (17)O1B—N1B1.4090 (14)
C1A—C2A—H2A119.5C5B—C4B—H4B120.1
C1A—C6A—H6A119.9C5B—C6B—H6B119.7
C1A—C7A—H7A116.6C5B—C6B—C1B120.60 (11)
C1B—C6B—H6B119.7C6A—C5A—C4A120.52 (11)
C1B—C7B—H7B116.7C6A—C5A—H5A119.7
C1B—C2B—H2B119.6C6A—C1A—C7A122.75 (10)
C2A—C3A—H3A120.0C6B—C5B—C4B120.20 (12)
C2A—C1A—C6A118.62 (11)C6B—C5B—H5B119.9
C2A—C1A—C7A118.62 (11)C6B—C1B—C7B122.82 (10)
C2B—C3B—C4B120.13 (11)C7A—C8A—H8A119.9
C2B—C3B—H3B119.9C7A—C8A—C9A120.18 (11)
C2B—C1B—C6B118.47 (11)C7B—C8B—C9B121.15 (12)
C2B—C1B—C7B118.71 (11)C7B—C8B—H8B119.4
C3A—C4A—H4A120.1C8A—C7A—C1A126.72 (11)
C3A—C4A—C5A119.75 (11)C8A—C7A—H7A116.6
C3A—C2A—H2A119.5C8A—C9A—H9A116.4
C3A—C2A—C1A120.94 (11)C8B—C9B—H9B116.8
C3B—C4B—H4B120.1C8B—C7B—C1B126.51 (11)
C3B—C4B—C5B119.72 (12)C8B—C7B—H7B116.7
C3B—C2B—C1B120.87 (12)C9A—C8A—H8A119.9
C3B—C2B—H2B119.6C9A—N1A—O1A112.58 (9)
C4A—C3A—H3A120.0C9B—C8B—H8B119.4
C4A—C3A—C2A119.91 (11)C9B—N1B—O1B112.73 (10)
C4A—C5A—H5A119.7N1A—C9A—C8A127.25 (11)
C4B—C5B—H5B119.9N1A—C9A—H9A116.4
C4B—C3B—H3B119.9N1A—O1A—H1A102.2 (13)
C5A—C4A—H4A120.1N1B—C9B—H9B116.8
C5A—C6A—H6A119.9N1B—C9B—C8B126.41 (12)
C5A—C6A—C1A120.24 (11)N1B—O1B—H1B102.2 (12)
C1A—C2A—C3A—C4A−1.0 (2)C6A—C1A—C2A—C3A1.73 (18)
C1A—C6A—C5A—C4A0.04 (18)C6B—C5B—C4B—C3B0.50 (19)
C1A—C7A—C8A—C9A−174.32 (11)C7A—C1A—C2A—C3A−177.00 (11)
C1B—C7B—C8B—C9B−179.24 (11)C7A—C1A—C6A—C5A177.43 (11)
C1B—C2B—C3B—C4B0.13 (18)C7B—C8B—C9B—N1B175.07 (12)
C2A—C1A—C6A—C5A−1.24 (17)C7B—C1B—C6B—C5B178.75 (12)
C2B—C3B—C4B—C5B−0.73 (19)C8A—C7A—C1A—C2A165.01 (12)
C2B—C1B—C6B—C5B−0.92 (18)C8A—C7A—C1A—C6A−13.66 (18)
C3B—C2B—C1B—C6B0.69 (18)C8B—C7B—C1B—C6B−9.56 (19)
C3B—C2B—C1B—C7B−179.00 (11)C8B—C7B—C1B—C2B170.11 (12)
C4B—C5B—C6B—C1B0.34 (19)N1A—C9A—C8A—C7A164.78 (12)
C5A—C4A—C3A—C2A−0.2 (2)O1A—N1A—C9A—C8A3.45 (17)
C6A—C5A—C4A—C3A0.71 (19)O1B—N1B—C9B—C8B−1.80 (18)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of rings C1A–C6A and C1B–C6B, respectively.
D—H···AD—HH···AD···AD—H···A
O1A—H1A···N1Bi0.91 (2)1.85 (2)2.755 (2)174 (2)
O1B—H1B···N1Aii0.92 (2)1.95 (2)2.853 (2)170 (2)
C2A—H2A···Cg1iii0.952.703.563 (2)151
C5B—H5B···Cg2iv0.952.803.508 (2)132
C9B—H9B···Cg2v0.952.823.717 (2)159
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1/2, y, −z+3/2; (iii) −x+3/2, y−1/2, z; (iv) −x+1/2, y−1/2, z; (v) −x+1, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of rings C1A–C6A and C1B–C6B, respectively.
D—H···AD—HH···AD···AD—H···A
O1A—H1A···N1Bi0.91 (2)1.85 (2)2.755 (2)174 (2)
O1B—H1B···N1Aii0.92 (2)1.95 (2)2.853 (2)170 (2)
C2A—H2A···Cg1iii0.952.703.563 (2)151
C5B—H5B···Cg2iv0.952.803.508 (2)132
C9B—H9B···Cg2v0.952.823.717 (2)159
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1/2, y, −z+3/2; (iii) −x+3/2, y−1/2, z; (iv) −x+1/2, y−1/2, z; (v) −x+1, y−1/2, −z+3/2.
 

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ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o1063-o1064
https://doi.org/10.1107/S2056989015023853
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