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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 70| Part 2| February 2014| Page o190
doi:10.1107/S1600536814001263

(E)-3-(9-Ethyl-9H-carbazol-3-yl)-1-(2-meth­­oxy­phen­yl)prop-2-en-1-one

Hongshan Lai,a Judith C. Galluccib and Chenglong Lia*

aDivision of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA, and bDepartment of Chemistry and Biochemistry, 100 West 18th Avenue, The Ohio State University, Columbus, OH 43210, USA
*Correspondence e-mail: li.728@osu.edu

(Received 3 January 2014; accepted 17 January 2014; online 22 January 2014)

In the title mol­ecule, C24H21NO2, the dihedral angle between the carbazole ring system [with a maximum deviation of 0.052 (2) Å] and the benzene ring is 38.6 (1)°. In the crystal, weak bifurcated (C—H)2⋯O hydrogen bonds link the mol­ecules into chains along [100].

CCDC reference: 982124

Related literature

For biological applications of the title compound, see: Caulfield et al. (2002[Caulfield, T., Cherrier, M.-P., Combeau, C. & Mailliet, P. (2002). Eur. Pat. Appl. 1253141.]). For the synthesis, see: Mazimba et al. (2011[Mazimba, O., Masesane, I. B. & Majinda, R. R. (2011). Tetrahedron Lett. 52, 6716-6718.]). For a related structure, see: Cao et al. (2005[Cao, D.-X., Li, G.-Z., Xue, G., Yu, W.-T. & Liu, Z.-Q. (2005). Acta Cryst. E61, o977-o979.]).

[Scheme 1]

Experimental

Crystal data

  • C24H21NO2

  • Mr = 355.42

  • Orthorhombic, P b c a

  • a = 15.9332 (7) Å

  • b = 7.8915 (3) Å

  • c = 30.4062 (14) Å

  • V = 3823.2 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 150 K

  • 0.35 × 0.27 × 0.02 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.746, Tmax = 0.998

  • 31757 measured reflections

  • 3352 independent reflections

  • 1845 reflections with I > 2σ(I)

  • Rint = 0.070
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.102

  • S = 1.00

  • 3352 reflections

  • 246 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O1i 0.95 2.48 3.387 (3) 160
C13—H13A⋯O1i 0.99 2.47 3.379 (3) 153
Symmetry code: (i) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: COLLECT (Bruker, 2008[Bruker (2008). COLLECT. Bruker AXS, Delft, The Netherlands.]); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: HKL DENZO (Otwinowski & Minor 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

CCDC reference: 982124

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814001263/lh5681sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001263/lh5681Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001263/lh5681Isup3.cml

checkCIF report


Comment top

The title compound (I) exhibits potential tubulin polymerization-inhibiting activity in drug discovery (Caulfield et al., 2002). It was obtained by reacting 1-(2-methoxyphenyl)ethanone and 9-ethyl-9H-carbazole-3-carbaldehyde through a modified procedure from Mazimba et al. (2011). The molecular structure of (I) is shown in Fig. 1. The fused ring system and the benzene ring are linked via an α,β-unsaturated carbonyl group so that the molecule has the potential to contain an extended π-conjugation system. However, there is distortion from a planar conformation, which is reflected in the dihedral angle between the carbazole ring system (with a maximum deviation of 0.052 (2)Å for C10) and the benzene ring which is 38.6 (1)°. The α, β-unsaturated carbonyl group is close to planar with a torsion angle of -4.2 (3)° for C15—C16—C17—O1 and forms a dihedral angle of 7.9 (1)° with the carbazole group, indicating some π conjugation between these two groups. A similar structure has been reported where the methoxy group on the benzene ring is substituted by a hydroxyl group (Cao et al., 2005). In this hydroxyl derivative the molecule is more planar, with a dihedral angle of 11.58 (12)° between the planes of the carbazole ring system and benzene ring. Also in the hydroxyl derivative, the hydroxyl group is involved in an intramolecular hydrogen bond with the oxygen atom of the ketone group. In molecule (I), the methoxy group is on the opposite side of the molecule from the ketone group as a result of an approximate 180° rotation about the C17—C18 bond, possibly to avoid steric interactions between atoms O1 and O2. In the crystal, weak bifurcated (C—H)2···O hydrogen bonds link molecules into chains along [100] (Fig. 2).

Related literature top

For biological applications of the title compound, see: Caulfield et al. (2002). For the synthesis, see: Mazimba et al. (2011). For a related structure, see: Cao et al. (2005).

Experimental top

All chemicals used were purchased from commercial sources and used without further purification. To a solution of 1-(2-methoxyphenyl)ethanone (1.5 g, 10 mmol) and 9-ethyl-9H-carbazole-3-carbaldehyde (2.23 g, 10 mmol) in MeOH (20 ml) was added 50% KOH (4 ml) aqueous solution dropwise with continuous stirring at room temperature. The reaction mixture was then refluxed for 4 h. The reaction suspension was poured onto cold H2O and the mixture was neutralized with 2 M HCl until the solution was acidic. A yellow solid was precipitated out, collected and washed with H2O. This solid was characterized by NMR to be the title compound. Crystals were grown from MeOH/H2O (50:1 v/v) solution by slow evaporation.

Refinement top

For each methyl group, the hydrogen atoms were added in calculated positions using a riding-model with C—H = 0.98 Å and U(H) = 1.5Ueq(C). The torsion angle, which defines the orientation of the methyl group about the C—C or O—C bond, was refined. The rest of the hydrogen atoms were included in calculated positions using a riding-model approximation with C—H = 0.95 to 0.99 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

The title compound (I) exhibits potential tubulin polymerization-inhibiting activity in drug discovery (Caulfield et al., 2002). It was obtained by reacting 1-(2-methoxyphenyl)ethanone and 9-ethyl-9H-carbazole-3-carbaldehyde through a modified procedure from Mazimba et al. (2011). The molecular structure of (I) is shown in Fig. 1. The fused ring system and the benzene ring are linked via an α,β-unsaturated carbonyl group so that the molecule has the potential to contain an extended π-conjugation system. However, there is distortion from a planar conformation, which is reflected in the dihedral angle between the carbazole ring system (with a maximum deviation of 0.052 (2)Å for C10) and the benzene ring which is 38.6 (1)°. The α, β-unsaturated carbonyl group is close to planar with a torsion angle of -4.2 (3)° for C15—C16—C17—O1 and forms a dihedral angle of 7.9 (1)° with the carbazole group, indicating some π conjugation between these two groups. A similar structure has been reported where the methoxy group on the benzene ring is substituted by a hydroxyl group (Cao et al., 2005). In this hydroxyl derivative the molecule is more planar, with a dihedral angle of 11.58 (12)° between the planes of the carbazole ring system and benzene ring. Also in the hydroxyl derivative, the hydroxyl group is involved in an intramolecular hydrogen bond with the oxygen atom of the ketone group. In molecule (I), the methoxy group is on the opposite side of the molecule from the ketone group as a result of an approximate 180° rotation about the C17—C18 bond, possibly to avoid steric interactions between atoms O1 and O2. In the crystal, weak bifurcated (C—H)2···O hydrogen bonds link molecules into chains along [100] (Fig. 2).

For biological applications of the title compound, see: Caulfield et al. (2002). For the synthesis, see: Mazimba et al. (2011). For a related structure, see: Cao et al. (2005).

Computing details top

Data collection: COLLECT (Bruker, 2008); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. Crystal packing of (I) showing weak C—H···O hydrogen bonds as dashed lines. Only H atoms involved in these hydrogen bonds are shown.
(E)-3-(9-Ethyl-9H-carbazol-3-yl)-1-(2-methoxyphenyl)prop-2-en-1-one top
Crystal data top
C24H21NO2F(000) = 1504
Mr = 355.42Dx = 1.235 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3814 reflections
a = 15.9332 (7) Åθ = 1.0–25.0°
b = 7.8915 (3) ŵ = 0.08 mm−1
c = 30.4062 (14) ÅT = 150 K
V = 3823.2 (3) Å3Rectangular plate, pale yellow
Z = 80.35 × 0.27 × 0.02 mm
Data collection top
Nonius KappaCCD
diffractometer		3352 independent reflections
Radiation source: Enraf Nonius FR5901845 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromatorRint = 0.070
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 1.3°
φ and ω scansh = −18→18
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)		k = −9→9
Tmin = 0.746, Tmax = 0.998l = −36→35
31757 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0412P)2 + 0.295P]
where P = (Fo2 + 2Fc2)/3
3352 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.14 e Å−3
0 constraints
Crystal data top
C24H21NO2V = 3823.2 (3) Å3
Mr = 355.42Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 15.9332 (7) ŵ = 0.08 mm−1
b = 7.8915 (3) ÅT = 150 K
c = 30.4062 (14) Å0.35 × 0.27 × 0.02 mm
Data collection top
Nonius KappaCCD
diffractometer		3352 independent reflections
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)		1845 reflections with I > 2σ(I)
Tmin = 0.746, Tmax = 0.998Rint = 0.070
31757 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.00Δρmax = 0.16 e Å−3
3352 reflectionsΔρmin = −0.14 e Å−3
246 parameters
Special details top

Experimental. All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler.

The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 3.0, which means that 90% of the data was measured at least 3.0 times. Phi and omega scans with a frame width of 0.9 degree were used. Data integration was done with DENZO, and scaling and merging of the data was done with SCALEPACK.

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. For each methyl group, the hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the C—C or O—C bond, was refined. The rest of the hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2 * Ueq(bonded atom).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.58107 (13)0.4180 (3)0.16865 (7)0.0365 (5)
C20.55972 (13)0.4813 (3)0.12727 (7)0.0425 (6)
H20.51370.43630.11120.051*
C30.60792 (14)0.6114 (3)0.11058 (7)0.0477 (6)
H30.59430.65740.08260.057*
C40.67642 (14)0.6775 (3)0.13385 (7)0.0492 (6)
H40.70890.76630.12140.059*
C50.69696 (13)0.6144 (3)0.17475 (7)0.0451 (6)
H50.74330.65940.19060.054*
C60.64896 (12)0.4840 (3)0.19261 (7)0.0345 (5)
C70.65009 (12)0.3956 (3)0.23405 (7)0.0339 (5)
C80.70128 (12)0.4038 (3)0.27101 (7)0.0362 (5)
H80.74750.47970.27140.043*
C90.68545 (12)0.3019 (3)0.30752 (7)0.0355 (5)
C100.61672 (12)0.1890 (3)0.30591 (7)0.0404 (6)
H100.60510.12030.33080.048*
C110.56615 (13)0.1754 (3)0.26952 (7)0.0410 (6)
H110.52070.09760.2690.049*
C120.58310 (12)0.2786 (3)0.23322 (7)0.0350 (5)
C130.47419 (13)0.1832 (3)0.17763 (7)0.0499 (7)
H13A0.43310.25240.1610.06*
H13B0.44470.13340.20320.06*
C140.50550 (18)0.0424 (3)0.14849 (9)0.0828 (9)
H14A0.53650.09070.12360.124*
H14B0.4577−0.02320.13750.124*
H14C0.5427−0.0320.16540.124*
C150.74185 (12)0.3152 (3)0.34485 (7)0.0372 (5)
H150.78670.39330.34130.045*
C160.74025 (12)0.2341 (3)0.38357 (7)0.0379 (5)
H160.6960.15730.390.045*
C170.80689 (13)0.2638 (3)0.41605 (7)0.0369 (5)
C180.80572 (12)0.1765 (3)0.45984 (7)0.0337 (5)
C190.88251 (13)0.1376 (3)0.47869 (7)0.0426 (6)
H190.93260.16630.46340.051*
C200.88829 (15)0.0581 (3)0.51919 (8)0.0493 (6)
H200.94160.03240.53150.059*
C210.81594 (16)0.0168 (3)0.54127 (7)0.0507 (6)
H210.8193−0.03870.56890.061*
C220.73854 (15)0.0549 (3)0.52376 (7)0.0468 (6)
H220.68890.02570.53930.056*
C230.73321 (13)0.1361 (3)0.48332 (7)0.0371 (5)
C240.58291 (13)0.1302 (3)0.48541 (8)0.0627 (7)
H24A0.58240.00610.48640.094*
H24B0.53480.17040.46820.094*
H24C0.57940.17530.51540.094*
N0.54168 (10)0.2928 (2)0.19338 (6)0.0396 (5)
O10.86753 (9)0.35552 (18)0.40737 (5)0.0474 (4)
O20.65910 (8)0.18701 (19)0.46524 (5)0.0484 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0346 (12)0.0392 (13)0.0359 (13)0.0007 (11)0.0055 (11)0.0002 (12)
C20.0404 (14)0.0500 (15)0.0371 (14)0.0000 (12)0.0011 (11)−0.0038 (12)
C30.0535 (15)0.0543 (16)0.0352 (14)0.0037 (14)0.0009 (12)0.0049 (13)
C40.0544 (15)0.0485 (16)0.0447 (15)−0.0076 (13)0.0043 (13)0.0064 (13)
C50.0425 (14)0.0499 (15)0.0430 (15)−0.0075 (12)−0.0024 (12)0.0011 (13)
C60.0329 (12)0.0359 (13)0.0346 (13)0.0000 (11)0.0021 (11)−0.0020 (11)
C70.0335 (12)0.0341 (13)0.0340 (13)0.0005 (11)0.0010 (11)−0.0009 (11)
C80.0314 (12)0.0358 (13)0.0413 (14)−0.0022 (11)0.0022 (11)−0.0006 (12)
C90.0332 (12)0.0354 (13)0.0379 (14)0.0015 (11)0.0005 (10)−0.0002 (11)
C100.0380 (13)0.0439 (14)0.0393 (14)−0.0003 (12)0.0020 (11)0.0048 (12)
C110.0344 (12)0.0417 (14)0.0467 (15)−0.0083 (11)0.0011 (11)0.0041 (12)
C120.0316 (12)0.0381 (13)0.0353 (13)0.0015 (11)0.0017 (10)−0.0004 (11)
C130.0438 (14)0.0623 (17)0.0436 (15)−0.0172 (13)−0.0059 (11)0.0042 (13)
C140.098 (2)0.063 (2)0.087 (2)−0.0234 (17)0.0054 (18)−0.0195 (17)
C150.0338 (12)0.0378 (13)0.0399 (14)−0.0011 (11)0.0003 (11)0.0002 (11)
C160.0325 (12)0.0418 (14)0.0392 (13)−0.0034 (11)0.0015 (11)−0.0002 (12)
C170.0333 (12)0.0384 (13)0.0391 (14)0.0014 (12)0.0042 (11)−0.0034 (11)
C180.0319 (12)0.0344 (13)0.0348 (13)−0.0029 (11)0.0014 (10)−0.0041 (10)
C190.0391 (13)0.0468 (15)0.0419 (15)−0.0024 (12)−0.0010 (11)−0.0014 (12)
C200.0488 (15)0.0516 (16)0.0477 (16)0.0036 (13)−0.0094 (13)−0.0023 (13)
C210.0688 (18)0.0469 (16)0.0364 (14)−0.0024 (15)−0.0019 (14)−0.0003 (12)
C220.0507 (16)0.0477 (15)0.0420 (15)−0.0090 (13)0.0101 (12)−0.0023 (12)
C230.0375 (14)0.0372 (13)0.0366 (14)0.0001 (11)−0.0004 (11)−0.0032 (11)
C240.0386 (14)0.0740 (18)0.0756 (18)−0.0062 (14)0.0152 (13)−0.0085 (15)
N0.0344 (10)0.0462 (12)0.0383 (11)−0.0048 (10)−0.0032 (9)0.0036 (10)
O10.0388 (9)0.0559 (10)0.0476 (10)−0.0099 (8)0.0025 (7)0.0022 (8)
O20.0336 (9)0.0624 (11)0.0493 (10)−0.0022 (8)0.0064 (7)0.0010 (8)
Geometric parameters (Å, º) top
C1—N1.391 (2)C13—H13B0.99
C1—C21.396 (3)C14—H14A0.98
C1—C61.404 (3)C14—H14B0.98
C2—C31.379 (3)C14—H14C0.98
C2—H20.95C15—C161.340 (3)
C3—C41.402 (3)C15—H150.95
C3—H30.95C16—C171.469 (3)
C4—C51.379 (3)C16—H160.95
C4—H40.95C17—O11.236 (2)
C5—C61.393 (3)C17—C181.499 (3)
C5—H50.95C18—C191.386 (3)
C6—C71.440 (3)C18—C231.395 (3)
C7—C81.390 (3)C19—C201.385 (3)
C7—C121.411 (3)C19—H190.95
C8—C91.394 (3)C20—C211.373 (3)
C8—H80.95C20—H200.95
C9—C101.412 (3)C21—C221.377 (3)
C9—C151.452 (3)C21—H210.95
C10—C111.373 (3)C22—C231.389 (3)
C10—H100.95C22—H220.95
C11—C121.398 (3)C23—O21.363 (2)
C11—H110.95C24—O21.432 (2)
C12—N1.384 (2)C24—H24A0.98
C13—N1.461 (2)C24—H24B0.98
C13—C141.506 (3)C24—H24C0.98
C13—H13A0.99
N—C1—C2129.15 (19)C13—C14—H14B109.5
N—C1—C6109.29 (18)H14A—C14—H14B109.5
C2—C1—C6121.5 (2)C13—C14—H14C109.5
C3—C2—C1117.5 (2)H14A—C14—H14C109.5
C3—C2—H2121.2H14B—C14—H14C109.5
C1—C2—H2121.2C16—C15—C9129.8 (2)
C2—C3—C4121.7 (2)C16—C15—H15115.1
C2—C3—H3119.2C9—C15—H15115.1
C4—C3—H3119.2C15—C16—C17120.0 (2)
C5—C4—C3120.4 (2)C15—C16—H16120
C5—C4—H4119.8C17—C16—H16120
C3—C4—H4119.8O1—C17—C16121.00 (19)
C4—C5—C6119.2 (2)O1—C17—C18117.93 (18)
C4—C5—H5120.4C16—C17—C18121.00 (19)
C6—C5—H5120.4C19—C18—C23118.0 (2)
C5—C6—C1119.7 (2)C19—C18—C17117.27 (19)
C5—C6—C7133.8 (2)C23—C18—C17124.75 (19)
C1—C6—C7106.50 (18)C20—C19—C18121.8 (2)
C8—C7—C12119.25 (18)C20—C19—H19119.1
C8—C7—C6133.78 (19)C18—C19—H19119.1
C12—C7—C6106.96 (17)C21—C20—C19119.1 (2)
C7—C8—C9120.71 (19)C21—C20—H20120.5
C7—C8—H8119.6C19—C20—H20120.5
C9—C8—H8119.6C20—C21—C22120.7 (2)
C8—C9—C10118.47 (19)C20—C21—H21119.6
C8—C9—C15117.97 (18)C22—C21—H21119.6
C10—C9—C15123.55 (19)C21—C22—C23119.9 (2)
C11—C10—C9122.2 (2)C21—C22—H22120.1
C11—C10—H10118.9C23—C22—H22120.1
C9—C10—H10118.9O2—C23—C22123.10 (19)
C10—C11—C12118.51 (19)O2—C23—C18116.32 (18)
C10—C11—H11120.7C22—C23—C18120.5 (2)
C12—C11—H11120.7O2—C24—H24A109.5
N—C12—C11130.25 (19)O2—C24—H24B109.5
N—C12—C7108.86 (17)H24A—C24—H24B109.5
C11—C12—C7120.86 (19)O2—C24—H24C109.5
N—C13—C14112.70 (19)H24A—C24—H24C109.5
N—C13—H13A109.1H24B—C24—H24C109.5
C14—C13—H13A109.1C12—N—C1108.39 (16)
N—C13—H13B109.1C12—N—C13126.16 (18)
C14—C13—H13B109.1C1—N—C13125.12 (18)
H13A—C13—H13B107.8C23—O2—C24117.99 (17)
C13—C14—H14A109.5
N—C1—C2—C3177.6 (2)C9—C15—C16—C17177.50 (19)
C6—C1—C2—C30.1 (3)C15—C16—C17—O1−4.2 (3)
C1—C2—C3—C40.6 (3)C15—C16—C17—C18179.06 (18)
C2—C3—C4—C5−0.7 (3)O1—C17—C18—C19−29.0 (3)
C3—C4—C5—C60.1 (3)C16—C17—C18—C19147.86 (19)
C4—C5—C6—C10.5 (3)O1—C17—C18—C23149.2 (2)
C4—C5—C6—C7−176.7 (2)C16—C17—C18—C23−33.9 (3)
N—C1—C6—C5−178.57 (18)C23—C18—C19—C201.2 (3)
C2—C1—C6—C5−0.6 (3)C17—C18—C19—C20179.58 (19)
N—C1—C6—C7−0.6 (2)C18—C19—C20—C21−0.1 (3)
C2—C1—C6—C7177.29 (18)C19—C20—C21—C22−0.6 (3)
C5—C6—C7—C8−2.6 (4)C20—C21—C22—C230.0 (3)
C1—C6—C7—C8179.9 (2)C21—C22—C23—O2−175.86 (19)
C5—C6—C7—C12178.0 (2)C21—C22—C23—C181.3 (3)
C1—C6—C7—C120.5 (2)C19—C18—C23—O2175.48 (18)
C12—C7—C8—C9−2.0 (3)C17—C18—C23—O2−2.7 (3)
C6—C7—C8—C9178.7 (2)C19—C18—C23—C22−1.8 (3)
C7—C8—C9—C100.6 (3)C17—C18—C23—C22179.97 (19)
C7—C8—C9—C15179.30 (18)C11—C12—N—C1177.8 (2)
C8—C9—C10—C110.9 (3)C7—C12—N—C1−0.2 (2)
C15—C9—C10—C11−177.79 (19)C11—C12—N—C13−8.5 (3)
C9—C10—C11—C12−0.8 (3)C7—C12—N—C13173.47 (18)
C10—C11—C12—N−178.5 (2)C2—C1—N—C12−177.2 (2)
C10—C11—C12—C7−0.7 (3)C6—C1—N—C120.5 (2)
C8—C7—C12—N−179.69 (17)C2—C1—N—C139.1 (3)
C6—C7—C12—N−0.2 (2)C6—C1—N—C13−173.23 (18)
C8—C7—C12—C112.1 (3)C14—C13—N—C12−95.3 (2)
C6—C7—C12—C11−178.43 (18)C14—C13—N—C177.3 (3)
C8—C9—C15—C16179.2 (2)C22—C23—O2—C24−10.3 (3)
C10—C9—C15—C16−2.1 (3)C18—C23—O2—C24172.48 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.483.387 (3)160
C13—H13A···O1i0.992.473.379 (3)153
Symmetry code: (i) x−1/2, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.483.387 (3)159.8
C13—H13A···O1i0.992.473.379 (3)153.1
Symmetry code: (i) x−1/2, y, −z+1/2.
 

Acknowledgements

We thank Dr Sihui Long for providing help with the crystallization.

References

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ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o190
doi:10.1107/S1600536814001263
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