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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1489–o1490.
Published online 2010 May 29. doi:  10.1107/S1600536810019434
PMCID: PMC2979436

(E)-N′-[(E)-2-Methyl­pent-2-enyl­idene]isonicotinohydrazide

Abstract

The asymmetric unit of the title Schiff base compound, C12H15N3O, contains two crystallographically independent mol­ecules, with both existing in an E configuration with respect to the C=N double bonds. In the crystal structure, inter­molecular N—H(...)N and C—H(...)O hydrogen bonds link the mol­ecules into a three-dimensional network.

Related literature

For the applications of isoniazid derivatives, see: Janin (2007 [triangle]); Maccari et al. (2005 [triangle]); Slayden & Barry (2000 [triangle]). For the bio­logical activity of Schiff bases, see: Kahwa et al. (1986 [triangle]). For related structures, see: Naveenkumar et al. (2009 [triangle]); Naveenkumar, Sadikun, Ibrahim, Quah & Fun (2010 [triangle]); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2010 [triangle]); Shi (2005 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]). For the synthesis, see: Lourenco et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1489-scheme1.jpg

Experimental

Crystal data

  • C12H15N3O
  • M r = 217.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1489-efi1.jpg
  • a = 19.809 (4) Å
  • b = 8.3459 (15) Å
  • c = 16.021 (3) Å
  • β = 119.825 (3)°
  • V = 2297.7 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.54 × 0.20 × 0.10 mm

Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.957, T max = 0.992
  • 12644 measured reflections
  • 3396 independent reflections
  • 2883 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.073
  • wR(F 2) = 0.225
  • S = 1.03
  • 3396 reflections
  • 301 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.15 e Å−3
  • Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019434/is2553sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019434/is2553Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This research was supported by Universiti Sains Malaysia (USM) under the Fundamental Research Grant Scheme (203/PFARMASI/671157). HKF and WSL thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). HSN and WSL are also grateful for the award of USM fellowships.

supplementary crystallographic information

Comment

In the search of new compounds, isoniazid derivatives have been found to possess potential tuberculostatic activity (Janin, 2007; Maccari et al., 2005; Slayden et al., 2000). Schiff bases have attracted much attention because of their biological activity (Kahwa et al., 1986). As a part of a current work of synthesis of (E)-N'-substituted isonicotinohydrazide derivatives, in this paper we present the crystal structure of the title compound.

The title Schiff base compound (Fig. 1), consists of two crystallographically independent molecules (molecule A & B). In the molecules, both pyridine rings (C1A/C2A/N1A/C3A–C5A & C1B/C2B/N1B/C3B–C5B) are approximately planar with maximum deviations of 0.006 (5) Å at atom C4A and 0.007 (6) Å at atom C3B. The molecules exist in an E configuration with respect to the C7A═N3A and C7B═N3B double bonds. Bond lengths (Allen et al., 1987) and the angles of the title compound are within the normal range and are closely related to comparable structures (Naveenkumar et al., 2009; Naveenkumar, Sadikun, Ibrahim, Quah & Fun, 2010; Naveenkumar, Sadikun, Ibrahim, Yeap & Fun, 2010; Shi, 2005).

In the crystal packing (Fig. 2), intermolecular N2B—H1NB···N1A, N2A—H1NA···N1B, C7B—H7BA···O1A and C12A—H12B···O1B hydrogen bonds (Table 1) link the molecules into a three-dimensional network.

Experimental

The isoniazid derivative was prepared following the procedure by Lourenco et al. (2008). The titled compound was prepared by reaction between the 2-methyl-2-pentenal (1.0 eq) with isoniazid (1.0 eq) in ethanol/water. After stirring for 1-3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue, purified by washing with cold ethanol and ethyl ether, afforded the pure derivative. The colourless single crystal suitable for X-ray analysis was obtained by recrystalization with methanol.

Refinement

H1NA and H1NB were located from a difference Fourier map and were refined freely [N–H = 0.83 (6) or 0.94 (6) Å]. The remaining H atoms were positioned geometrically (C–H = 0.93–0.97 Å) and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to all the methyl groups. In the final difference Fourier map, the highest peak is 1.08 Å from atom H11E and the deepest hole is 0.59 Å from atom C9B. In the absence of significant anomalous dispersion, 2998 Friedel pairs were merged before the final refinement.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound, viewed along the b axis. Intermolecular interactions are shown as dashed lines. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C12H15N3OF(000) = 928
Mr = 217.27Dx = 1.256 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3734 reflections
a = 19.809 (4) Åθ = 2.7–30.1°
b = 8.3459 (15) ŵ = 0.08 mm1
c = 16.021 (3) ÅT = 100 K
β = 119.825 (3)°Plate, colourless
V = 2297.7 (7) Å30.54 × 0.20 × 0.10 mm
Z = 8

Data collection

Bruker APEXII DUO CCD area-detector diffractometer3396 independent reflections
Radiation source: fine-focus sealed tube2883 reflections with I > 2σ(I)
graphiteRint = 0.044
[var phi] and ω scansθmax = 30.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −28→27
Tmin = 0.957, Tmax = 0.992k = −11→11
12644 measured reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.158P)2 + 2.1081P] where P = (Fo2 + 2Fc2)/3
3396 reflections(Δ/σ)max = 0.001
301 parametersΔρmax = 1.15 e Å3
2 restraintsΔρmin = −0.47 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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.
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)

xyzUiso*/Ueq
O1A0.45226 (16)0.4174 (4)0.2514 (2)0.0279 (6)
N1A0.50282 (19)0.5795 (5)−0.0143 (2)0.0270 (7)
N2A0.33160 (18)0.4903 (4)0.1323 (2)0.0222 (6)
N3A0.29513 (18)0.4476 (4)0.1835 (2)0.0222 (6)
C1A0.3923 (2)0.5171 (5)0.0042 (2)0.0228 (7)
H1AA0.33910.4982−0.02470.027*
C2A0.4267 (2)0.5523 (5)−0.0517 (3)0.0245 (7)
H2AA0.39500.5570−0.11820.029*
C3A0.5470 (2)0.5727 (6)0.0815 (3)0.0332 (9)
H3AA0.60000.59260.10870.040*
C4A0.5184 (2)0.5376 (6)0.1427 (3)0.0307 (8)
H4AA0.55160.53220.20890.037*
C5A0.4391 (2)0.5108 (5)0.1032 (3)0.0233 (7)
C6A0.4089 (2)0.4684 (5)0.1703 (2)0.0219 (7)
C7A0.2215 (2)0.4758 (4)0.1376 (3)0.0224 (6)
H7AA0.19940.51970.07620.027*
C8A0.1715 (2)0.4418 (5)0.1777 (3)0.0256 (7)
C9A0.0963 (3)0.4814 (6)0.1240 (3)0.0356 (9)
H9AA0.08120.52470.06380.043*
C10A0.0337 (3)0.4641 (7)0.1499 (4)0.0429 (11)
H10A0.05680.42990.21640.052*
H10B−0.00260.38180.10990.052*
C11A−0.0096 (3)0.6178 (7)0.1369 (4)0.0448 (12)
H11A−0.05080.60050.15100.067*
H11B−0.03110.65390.07170.067*
H11C0.02540.69750.17980.067*
C12A0.2060 (2)0.3646 (6)0.2752 (3)0.0301 (8)
H12A0.17340.27740.27270.045*
H12B0.20960.44220.32140.045*
H12C0.25700.32480.29360.045*
O1B0.20324 (15)0.6331 (3)0.4358 (2)0.0268 (6)
N1B0.2523 (2)1.2198 (4)0.5118 (3)0.0330 (8)
N2B0.08523 (17)0.7236 (4)0.4095 (2)0.0236 (6)
N3B0.04966 (18)0.5750 (4)0.3851 (2)0.0241 (6)
C1B0.14199 (19)1.0456 (5)0.4260 (2)0.0219 (7)
H1BA0.08861.03490.38520.026*
C2B0.1756 (2)1.1958 (5)0.4529 (3)0.0256 (7)
H2BA0.14341.28510.42910.031*
C3B0.2969 (3)1.0896 (6)0.5452 (4)0.0464 (13)
H3BA0.34991.10390.58690.056*
C4B0.2692 (2)0.9350 (5)0.5217 (4)0.0392 (11)
H4BA0.30300.84830.54590.047*
C5B0.1895 (2)0.9105 (4)0.4610 (3)0.0241 (7)
C6B0.1606 (2)0.7417 (4)0.4338 (2)0.0230 (7)
C7B−0.0233 (2)0.5835 (5)0.3572 (3)0.0286 (8)
H7BA−0.04630.68340.35020.034*
C8B−0.0706 (2)0.4398 (5)0.3366 (4)0.0354 (10)
C9B−0.1419 (3)0.4525 (7)0.3267 (5)0.0529 (15)
H9BA−0.15800.55590.32970.063*
C10B−0.1989 (3)0.3214 (7)0.3113 (5)0.0497 (13)
H10C−0.18760.22900.28360.060*
H10D−0.19260.28960.37300.060*
C11B−0.2777 (4)0.3700 (8)0.2492 (8)0.072 (2)
H11D−0.31230.28790.24760.108*
H11E−0.28610.38700.18550.108*
H11F−0.28760.46770.27290.108*
C12B−0.0352 (3)0.2825 (5)0.3361 (4)0.0387 (10)
H12D−0.07440.20080.31320.058*
H12E0.00500.25680.40020.058*
H12F−0.01320.28860.29460.058*
H1NB0.059 (3)0.808 (7)0.421 (4)0.023 (11)*
H1NA0.306 (3)0.543 (7)0.082 (4)0.028 (13)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0188 (12)0.0390 (16)0.0207 (12)0.0013 (11)0.0059 (10)0.0045 (11)
N1A0.0189 (14)0.0374 (18)0.0235 (15)−0.0008 (12)0.0098 (12)0.0006 (13)
N2A0.0157 (13)0.0295 (15)0.0201 (14)0.0012 (11)0.0079 (11)0.0049 (12)
N3A0.0198 (14)0.0243 (14)0.0219 (13)−0.0011 (11)0.0099 (11)0.0020 (11)
C1A0.0157 (14)0.0303 (17)0.0187 (15)−0.0021 (12)0.0056 (12)−0.0013 (13)
C2A0.0175 (15)0.0339 (19)0.0173 (14)0.0015 (13)0.0051 (12)0.0014 (13)
C3A0.0150 (15)0.055 (3)0.0224 (17)−0.0095 (16)0.0041 (13)0.0000 (17)
C4A0.0162 (16)0.048 (2)0.0202 (16)−0.0066 (15)0.0030 (13)0.0004 (15)
C5A0.0122 (14)0.0301 (17)0.0211 (15)−0.0009 (12)0.0034 (12)0.0021 (13)
C6A0.0161 (14)0.0251 (16)0.0195 (15)−0.0022 (12)0.0051 (12)−0.0028 (12)
C7A0.0184 (15)0.0255 (16)0.0196 (14)0.0002 (12)0.0067 (12)0.0020 (13)
C8A0.0186 (16)0.0363 (19)0.0204 (16)0.0034 (14)0.0087 (13)0.0004 (14)
C9A0.0235 (19)0.052 (3)0.0292 (19)0.0060 (18)0.0117 (16)0.0065 (19)
C10A0.030 (2)0.050 (3)0.052 (3)0.006 (2)0.024 (2)0.008 (2)
C11A0.038 (3)0.050 (3)0.052 (3)0.009 (2)0.026 (2)0.005 (2)
C12A0.0236 (17)0.040 (2)0.0255 (17)0.0012 (15)0.0113 (14)0.0032 (16)
O1B0.0165 (11)0.0251 (12)0.0306 (13)0.0023 (9)0.0056 (10)−0.0032 (11)
N1B0.0257 (16)0.0244 (15)0.0346 (17)−0.0034 (13)0.0042 (14)−0.0038 (14)
N2B0.0130 (12)0.0264 (15)0.0249 (14)−0.0001 (11)0.0046 (11)−0.0037 (12)
N3B0.0202 (14)0.0238 (14)0.0230 (14)−0.0024 (11)0.0066 (12)−0.0003 (11)
C1B0.0153 (14)0.0267 (17)0.0189 (14)0.0028 (12)0.0049 (12)0.0007 (12)
C2B0.0231 (16)0.0265 (17)0.0236 (15)0.0000 (13)0.0088 (13)−0.0017 (13)
C3B0.0202 (18)0.031 (2)0.055 (3)−0.0013 (16)−0.0055 (18)−0.008 (2)
C4B0.0148 (16)0.0258 (18)0.050 (3)0.0010 (13)−0.0046 (16)−0.0063 (17)
C5B0.0164 (14)0.0235 (16)0.0236 (16)0.0006 (12)0.0034 (13)−0.0033 (13)
C6B0.0181 (15)0.0240 (16)0.0200 (14)−0.0001 (12)0.0043 (12)−0.0018 (12)
C7B0.0191 (15)0.0243 (17)0.0342 (19)−0.0018 (13)0.0071 (14)−0.0075 (15)
C8B0.0235 (18)0.0281 (19)0.050 (3)−0.0089 (15)0.0144 (18)−0.0160 (18)
C9B0.032 (2)0.040 (3)0.081 (4)−0.010 (2)0.023 (3)−0.021 (3)
C10B0.041 (3)0.041 (3)0.064 (3)−0.006 (2)0.023 (3)−0.006 (2)
C11B0.055 (4)0.044 (3)0.137 (8)−0.010 (3)0.063 (5)−0.020 (4)
C12B0.036 (2)0.0262 (19)0.063 (3)−0.0065 (16)0.032 (2)−0.0093 (19)

Geometric parameters (Å, °)

O1A—C6A1.223 (5)O1B—C6B1.228 (5)
N1A—C2A1.337 (5)N1B—C3B1.333 (6)
N1A—C3A1.338 (5)N1B—C2B1.346 (5)
N2A—C6A1.350 (4)N2B—C6B1.350 (4)
N2A—N3A1.382 (4)N2B—N3B1.383 (4)
N2A—H1NA0.83 (6)N2B—H1NB0.94 (6)
N3A—C7A1.287 (5)N3B—C7B1.284 (5)
C1A—C5A1.384 (5)C1B—C2B1.384 (5)
C1A—C2A1.399 (5)C1B—C5B1.395 (5)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.385 (6)C3B—C4B1.379 (6)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.389 (5)C4B—C5B1.397 (5)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.510 (5)C5B—C6B1.502 (5)
C7A—C8A1.451 (5)C7B—C8B1.456 (6)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—C9A1.340 (5)C8B—C9B1.344 (7)
C8A—C12A1.503 (5)C8B—C12B1.490 (6)
C9A—C10A1.496 (6)C9B—C10B1.502 (8)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.499 (8)C10B—C11B1.431 (10)
C10A—H10A0.9700C10B—H10C0.9700
C10A—H10B0.9700C10B—H10D0.9700
C11A—H11A0.9600C11B—H11D0.9600
C11A—H11B0.9600C11B—H11E0.9600
C11A—H11C0.9600C11B—H11F0.9600
C12A—H12A0.9600C12B—H12D0.9600
C12A—H12B0.9600C12B—H12E0.9600
C12A—H12C0.9600C12B—H12F0.9600
C2A—N1A—C3A117.0 (3)C3B—N1B—C2B116.8 (4)
C6A—N2A—N3A120.5 (3)C6B—N2B—N3B121.1 (3)
C6A—N2A—H1NA121 (4)C6B—N2B—H1NB119 (3)
N3A—N2A—H1NA117 (4)N3B—N2B—H1NB119 (3)
C7A—N3A—N2A113.0 (3)C7B—N3B—N2B112.1 (3)
C5A—C1A—C2A118.6 (3)C2B—C1B—C5B118.9 (3)
C5A—C1A—H1AA120.7C2B—C1B—H1BA120.6
C2A—C1A—H1AA120.7C5B—C1B—H1BA120.6
N1A—C2A—C1A123.3 (3)N1B—C2B—C1B123.6 (4)
N1A—C2A—H2AA118.3N1B—C2B—H2BA118.2
C1A—C2A—H2AA118.3C1B—C2B—H2BA118.2
N1A—C3A—C4A123.9 (4)N1B—C3B—C4B124.0 (4)
N1A—C3A—H3AA118.1N1B—C3B—H3BA118.0
C4A—C3A—H3AA118.1C4B—C3B—H3BA118.0
C3A—C4A—C5A118.6 (4)C3B—C4B—C5B119.0 (4)
C3A—C4A—H4AA120.7C3B—C4B—H4BA120.5
C5A—C4A—H4AA120.7C5B—C4B—H4BA120.5
C1A—C5A—C4A118.5 (3)C1B—C5B—C4B117.7 (3)
C1A—C5A—C6A123.3 (3)C1B—C5B—C6B123.9 (3)
C4A—C5A—C6A118.1 (3)C4B—C5B—C6B118.4 (3)
O1A—C6A—N2A124.5 (3)O1B—C6B—N2B125.0 (3)
O1A—C6A—C5A121.4 (3)O1B—C6B—C5B121.7 (3)
N2A—C6A—C5A114.2 (3)N2B—C6B—C5B113.3 (3)
N3A—C7A—C8A122.7 (3)N3B—C7B—C8B121.3 (4)
N3A—C7A—H7AA118.7N3B—C7B—H7BA119.4
C8A—C7A—H7AA118.7C8B—C7B—H7BA119.4
C9A—C8A—C7A117.0 (4)C9B—C8B—C7B118.8 (4)
C9A—C8A—C12A123.9 (4)C9B—C8B—C12B122.6 (4)
C7A—C8A—C12A119.1 (3)C7B—C8B—C12B118.4 (4)
C8A—C9A—C10A127.5 (4)C8B—C9B—C10B128.5 (5)
C8A—C9A—H9AA116.3C8B—C9B—H9BA115.8
C10A—C9A—H9AA116.3C10B—C9B—H9BA115.8
C9A—C10A—C11A112.0 (5)C11B—C10B—C9B112.3 (6)
C9A—C10A—H10A109.2C11B—C10B—H10C109.1
C11A—C10A—H10A109.2C9B—C10B—H10C109.1
C9A—C10A—H10B109.2C11B—C10B—H10D109.1
C11A—C10A—H10B109.2C9B—C10B—H10D109.1
H10A—C10A—H10B107.9H10C—C10B—H10D107.9
C10A—C11A—H11A109.5C10B—C11B—H11D109.5
C10A—C11A—H11B109.5C10B—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
C10A—C11A—H11C109.5C10B—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
C8A—C12A—H12A109.5C8B—C12B—H12D109.5
C8A—C12A—H12B109.5C8B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C8A—C12A—H12C109.5C8B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
C6A—N2A—N3A—C7A−179.9 (3)C6B—N2B—N3B—C7B−175.0 (4)
C3A—N1A—C2A—C1A−0.3 (6)C3B—N1B—C2B—C1B−0.3 (7)
C5A—C1A—C2A—N1A0.4 (6)C5B—C1B—C2B—N1B−0.2 (6)
C2A—N1A—C3A—C4A0.7 (7)C2B—N1B—C3B—C4B1.1 (9)
N1A—C3A—C4A—C5A−1.3 (8)N1B—C3B—C4B—C5B−1.5 (10)
C2A—C1A—C5A—C4A−0.9 (6)C2B—C1B—C5B—C4B−0.2 (6)
C2A—C1A—C5A—C6A−177.8 (3)C2B—C1B—C5B—C6B−177.4 (4)
C3A—C4A—C5A—C1A1.3 (7)C3B—C4B—C5B—C1B0.9 (8)
C3A—C4A—C5A—C6A178.4 (4)C3B—C4B—C5B—C6B178.3 (5)
N3A—N2A—C6A—O1A−3.1 (6)N3B—N2B—C6B—O1B0.6 (6)
N3A—N2A—C6A—C5A176.2 (3)N3B—N2B—C6B—C5B−178.2 (3)
C1A—C5A—C6A—O1A157.8 (4)C1B—C5B—C6B—O1B153.4 (4)
C4A—C5A—C6A—O1A−19.2 (6)C4B—C5B—C6B—O1B−23.8 (6)
C1A—C5A—C6A—N2A−21.5 (5)C1B—C5B—C6B—N2B−27.8 (5)
C4A—C5A—C6A—N2A161.5 (4)C4B—C5B—C6B—N2B155.0 (4)
N2A—N3A—C7A—C8A−179.5 (4)N2B—N3B—C7B—C8B−174.3 (4)
N3A—C7A—C8A—C9A177.8 (4)N3B—C7B—C8B—C9B166.8 (6)
N3A—C7A—C8A—C12A−2.5 (6)N3B—C7B—C8B—C12B−7.8 (7)
C7A—C8A—C9A—C10A−177.9 (5)C7B—C8B—C9B—C10B−176.0 (6)
C12A—C8A—C9A—C10A2.4 (8)C12B—C8B—C9B—C10B−1.7 (11)
C8A—C9A—C10A—C11A127.7 (6)C8B—C9B—C10B—C11B−144.2 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2B—H1NB···N1Ai0.95 (6)2.08 (6)2.973 (5)156 (5)
N2A—H1NA···N1Bii0.83 (6)2.26 (6)3.005 (5)148 (5)
C7B—H7BA···O1Aiii0.932.513.171 (5)129
C12A—H12B···O1B0.962.483.433 (5)173

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) x, −y+2, z−1/2; (iii) x−1/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2553).

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