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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o493.
Published online 2008 January 23. doi:  10.1107/S1600536808001657
PMCID: PMC2960190

(E)-N-[2-(9-Fluorenyl­idene)-3a,5,7-tri­methyl-3,3a-dihydro-2H-indol-3-yl­idene]-2,4,6-trimethyl­aniline

Abstract

The title compound, C33H30N2, has an E configuration at the imine double bond. The angle between the least-squares planes of the imine C=N—C group and the benzene ring of the 2,4,6-trimethylphenyl substituent is 85.38 (11)°. The crystal structure is sustained mainly by inter­molecular π–π inter­actions (3.510 Å) between the two fluorene rings and some C—H(...)π inter­actions.

Related literature

For related literature, see: Döpp et al. (1985 [triangle]); Gerlach & Arnold (1997 [triangle]); Miyata et al. (1999 [triangle]); Mizuhata et al. (2005 [triangle]); Murakami et al. (1996 [triangle]); Shimizu et al. (1991 [triangle]).

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Object name is e-64-0o493-scheme1.jpg

Experimental

Crystal data

  • C33H30N2
  • M r = 454.59
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o493-efi3.jpg
  • a = 10.2810 (2) Å
  • b = 11.2727 (3) Å
  • c = 21.6598 (5) Å
  • β = 102.5953 (16)°
  • V = 2449.84 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 103 (2) K
  • 0.20 × 0.20 × 0.05 mm

Data collection

  • Rigaku Mercury diffractometer
  • Absorption correction: multi-scan (REQAB; Jacobson, 1998 [triangle]) T min = 0.986, T max = 0.996
  • 15962 measured reflections
  • 4289 independent reflections
  • 2994 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.096
  • S = 1.02
  • 4289 reflections
  • 407 parameters
  • Only H-atom coordinates refined
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2004 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: yadokari-XG (Wakita, 2005 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001657/om2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001657/om2207Isup2.hkl

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

Acknowledgments

This work was partially supported by Grants-in-Aid for Creative Scientific Research (No. 17GS0207), the 21st Century COE Program B14 (Kyoto University Alliance for Chemistry), and the Global COE Program B09 (International Center for Integrated Research and Advanced Education in Materials Science) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

supplementary crystallographic information

Comment

The structural analysis of 3aH-indole, one isomer of indole, has not been achieved due to its instability. On the other hand, the structures of some compounds based on the 3aH-indole skeleton, that is, 3,3a-dihydro-2H-indole derivertives (Döpp et al., 1985; Miyata et al., 1999; Shimizu et al., 1991) and 3,3a-dihydro-2H-indol-2,3-diylidene derivertives (Gerlach et al., 1997; Murakami et al., 1996), have been reported. During our course of studies on the reactivity of a stable stannene (tin–carbon double-bond compound) (Mizuhata et al., 2005), the crystal structure of a new example of 3,3a-dihydro-2H-indol-2,3-diylidene derivertives has been revealed.

The title compound was obtained in 29% yield by the reaction of a stannene, Tbt(Mes)Sn?(9-fluorenylidene) (Tbt = 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl; Mes = mesityl), with mesityl isocyanyde. The molecular structure of the title compound is shown in Fig. 1. It was found that the mesityl group is located with cis configuration to 3,3a-dihydro-2H-indole core with respect to the imine framework. The bond lengths in the 3,3a-dihydro-2H-indole core (C10—C17 and N2) are quite similar to those for the related compounds reported previously. However, the C10—C11 bond length [1.501 (3) Å] is longer than those of other 3,3a-dihydro-2H-indol-2,3-diylidene derivertives [1.456 (6) Å (Gerlach et al.); 1.456 (2) Å (Murakami et al.)] and shorter than those of the 3,3a-dihydro-2H-indole derivertives [1.553 (3) Å (Döpp et al.); 1.566 (3) Å (Miyata et al.); 1.565 (5) Å (Shimizu et al.)]. The distance between the least squares planes of the center rings of the fluorenylidene groups C29—C30—C31—C32—C33 and C29i—C30i—C31i—C32i—C33i (symmetry code: (i) = -x, -y, -z) is 3.510 Å (Fig. 2). The shortest intermolecular contacts were found to be H15—C24iii [2.74 (2) Å], H17—C2ii [2.70 (2) Å], and H25iii—C5ii [2.82 (2) Å] (symmetry codes: (ii) 1 + x, +y, +z; (iii) 1/2 + x, 1/2 - y, 1/2 + z).

Experimental

In a glovebox filled with argon, mesityl isocyanide (7.5 mg, 0.052 mmol) was added to a diethylether (2 ml) solution of Tbt(Mes)Sn?(9-fluorenylidene) [prepared from Tbt(Mes)(9-fluorenyl)SnF (39.3 mg, 0.0403 mmol) and tert-butyllithium (0.95 M in hexane, 0.043 ml, 0.041 mmol)] at room temperature. The reaction mixture was stirred for 15 h at room temperature. After removal of the solvent, the residue was separated by gel permeation liquid chromatography (eluted with CHCl3) to afford the title compound (5.2 mg, 0.0117 mmol, 29%) and MesN?C?(9-fluorenylidene) (3.7 mg, 0.0124 mmol, 31%). Single crystals of the title compound suitable for X-ray crystallographic analysis were obtained as red crystals by slow recrystallization of its benzene solution at room temperature. Physical data: m.p. 411 K (decomposition); 1H NMR (300 MHz, CDCl3, 298 K): δ 1.21 (s, 3H), 1.67 (s, 3H), 1.91 (s, 3H), 2.23 (s, 3H), 2.28 (s, 3H), 2.34 (s, 3H), 5.22 (s, 1H), 6.25 (s, 1H), 6.88 (s, 1H), 6.96 (s, 1H), 7.13–7.19 (m, 1H), 7.29–7.36 (m, 3H), 7.68–7.70 (m, 2H), 9.06–9.08 (m, 1H), 9.47 (d, 3J = 8.0 Hz, 1H).

Refinement

All H atoms were refined with U tied to the bonded C atom: 1.2(Uiso) for C—H and 1.5(Uiso) for CH3 groups while all the other atoms were refined anisotropically.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
The molecular packing of the title compound. Dashed lines indicate the C–H···π intramolecular contacts [Symmetry codes: (i) -x, -y, -z; (ii) 1 + x, +y, +z; (iii) 1/2 + x, 1/2 - y, 1/2 + z].

Crystal data

C33H30N2F000 = 968
Mr = 454.59Dx = 1.233 Mg m3
Monoclinic, P21/nMelting point: 411 K
Hall symbol: -P 2ynMo Kα radiation λ = 0.71069 Å
a = 10.2810 (2) Åθ = 3.4–25.0º
b = 11.2727 (3) ŵ = 0.07 mm1
c = 21.6598 (5) ÅT = 103 (2) K
β = 102.5953 (16)ºPrism, red
V = 2449.84 (10) Å30.20 × 0.20 × 0.05 mm
Z = 4

Data collection

Rigaku Mercury CCD diffractometer2994 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
T = 103(2) Kθmax = 25.0º
ω scansθmin = 3.4º
Absorption correction: multi-scan(REQAB; Jacobson, 1998)h = −12→12
Tmin = 0.986, Tmax = 0.996k = −13→10
15962 measured reflectionsl = −24→25
4289 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullOnly H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.040  w = 1/[σ2(Fo2) + (0.0373P)2 + 0.5999P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.25 e Å3
4289 reflectionsΔρmin = −0.19 e Å3
407 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0043 (6)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
N1−0.03226 (14)0.03480 (13)0.22158 (7)0.0217 (4)
C1−0.06655 (17)−0.00324 (16)0.27895 (8)0.0202 (4)
C2−0.13560 (17)−0.10987 (16)0.28032 (8)0.0206 (4)
C3−0.17530 (18)−0.14060 (17)0.33593 (9)0.0236 (4)
H1−0.2217 (19)−0.2182 (17)0.3372 (8)0.028*
C4−0.15066 (18)−0.06749 (17)0.38866 (9)0.0244 (4)
C5−0.08538 (18)0.03968 (17)0.38498 (9)0.0241 (4)
H2−0.0656 (18)0.0949 (17)0.4239 (9)0.029*
C6−0.04435 (17)0.07451 (16)0.33063 (8)0.0215 (4)
C7−0.1717 (2)−0.18698 (18)0.22225 (9)0.0264 (4)
H3−0.217 (2)−0.1430 (18)0.1834 (10)0.040*
H4−0.235 (2)−0.2524 (19)0.2296 (9)0.040*
H5−0.093 (2)−0.2258 (18)0.2107 (9)0.040*
C8−0.1956 (2)−0.1004 (2)0.44821 (10)0.0340 (5)
H6−0.263 (2)−0.168 (2)0.4403 (10)0.051*
H7−0.236 (2)−0.037 (2)0.4631 (10)0.051*
H8−0.122 (2)−0.128 (2)0.4809 (10)0.051*
C90.0248 (2)0.19139 (18)0.32799 (10)0.0284 (5)
H90.123 (2)0.1829 (18)0.3322 (9)0.043*
H100.012 (2)0.2472 (19)0.3629 (10)0.043*
H11−0.009 (2)0.2346 (19)0.2868 (10)0.043*
N20.26870 (14)0.06119 (13)0.16733 (7)0.0210 (3)
C100.12774 (17)0.06370 (15)0.15398 (8)0.0202 (4)
C110.08304 (17)0.01780 (15)0.21100 (8)0.0195 (4)
C120.24414 (18)−0.03646 (16)0.32202 (8)0.0219 (4)
H120.1716 (18)−0.0559 (16)0.3459 (8)0.026*
C130.37190 (18)−0.02512 (16)0.35192 (8)0.0228 (4)
C140.47680 (18)−0.00966 (16)0.31602 (9)0.0246 (4)
H130.572 (2)−0.0065 (16)0.3402 (9)0.030*
C150.45125 (17)0.00537 (15)0.25265 (9)0.0218 (4)
C160.20669 (17)−0.04503 (16)0.25098 (8)0.0200 (4)
C170.31158 (17)0.00802 (15)0.22083 (8)0.0202 (4)
C180.4151 (2)−0.03166 (19)0.42276 (9)0.0298 (5)
H140.335 (2)−0.0437 (19)0.4425 (10)0.045*
H150.464 (2)0.0443 (19)0.4412 (10)0.045*
H160.479 (2)−0.102 (2)0.4354 (9)0.045*
C190.55426 (19)0.0312 (2)0.21488 (10)0.0278 (5)
H170.647 (2)0.0295 (18)0.2433 (10)0.042*
H180.537 (2)0.110 (2)0.1915 (9)0.042*
H190.549 (2)−0.0275 (19)0.1806 (10)0.042*
C200.1947 (2)−0.17994 (16)0.23507 (9)0.0235 (4)
H200.1700 (19)−0.1935 (17)0.1864 (10)0.035*
H210.127 (2)−0.2187 (17)0.2562 (9)0.035*
H220.284 (2)−0.2210 (18)0.2533 (9)0.035*
C210.25981 (19)0.18750 (17)0.05033 (9)0.0261 (5)
H230.3320 (19)0.1725 (17)0.0886 (9)0.031*
C220.2922 (2)0.24009 (18)−0.00252 (9)0.0287 (5)
H240.387 (2)0.2675 (17)−0.0003 (9)0.034*
C230.1956 (2)0.26124 (17)−0.05731 (9)0.0273 (5)
H250.2183 (19)0.2987 (17)−0.0947 (9)0.033*
C240.0637 (2)0.23048 (16)−0.05992 (9)0.0256 (4)
H26−0.005 (2)0.2484 (16)−0.0991 (9)0.031*
C25−0.22427 (19)0.14758 (17)−0.03726 (9)0.0256 (4)
H27−0.2330 (18)0.1752 (17)−0.0804 (9)0.031*
C26−0.3349 (2)0.11042 (17)−0.01557 (9)0.0281 (5)
H28−0.425 (2)0.1090 (17)−0.0438 (9)0.034*
C27−0.3212 (2)0.07354 (17)0.04646 (9)0.0280 (5)
H29−0.398 (2)0.0512 (17)0.0631 (9)0.034*
C28−0.19683 (18)0.07043 (16)0.08820 (9)0.0250 (4)
H30−0.1866 (18)0.0447 (16)0.1337 (9)0.030*
C290.06016 (17)0.10611 (16)0.09684 (8)0.0201 (4)
C300.12739 (18)0.15654 (15)0.04819 (8)0.0205 (4)
C310.03035 (18)0.17914 (15)−0.00726 (8)0.0209 (4)
C32−0.10020 (18)0.14522 (15)0.00361 (8)0.0214 (4)
C33−0.08408 (18)0.10508 (15)0.06673 (8)0.0205 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0207 (8)0.0246 (9)0.0202 (8)0.0006 (7)0.0055 (7)0.0002 (7)
C10.0153 (9)0.0266 (10)0.0188 (10)0.0045 (8)0.0039 (8)0.0037 (8)
C20.0159 (9)0.0228 (10)0.0225 (10)0.0027 (8)0.0027 (8)0.0005 (8)
C30.0194 (10)0.0238 (10)0.0282 (11)0.0026 (8)0.0066 (8)0.0034 (9)
C40.0187 (10)0.0302 (11)0.0259 (10)0.0051 (8)0.0084 (8)0.0035 (9)
C50.0191 (10)0.0311 (11)0.0222 (10)0.0041 (8)0.0048 (8)−0.0026 (9)
C60.0144 (9)0.0250 (10)0.0249 (10)0.0027 (7)0.0040 (8)−0.0009 (8)
C70.0235 (11)0.0276 (11)0.0269 (11)−0.0028 (9)0.0030 (9)−0.0026 (9)
C80.0338 (13)0.0398 (13)0.0313 (12)0.0034 (10)0.0136 (10)0.0056 (10)
C90.0270 (11)0.0265 (11)0.0329 (12)−0.0024 (9)0.0090 (10)−0.0051 (9)
N20.0184 (8)0.0226 (8)0.0222 (8)0.0006 (7)0.0046 (7)0.0005 (7)
C100.0198 (9)0.0196 (9)0.0221 (10)0.0010 (8)0.0065 (8)−0.0003 (8)
C110.0197 (10)0.0197 (9)0.0188 (9)−0.0005 (7)0.0035 (8)−0.0025 (8)
C120.0231 (10)0.0227 (10)0.0203 (10)0.0029 (8)0.0054 (8)0.0010 (8)
C130.0239 (10)0.0219 (10)0.0213 (10)0.0021 (8)0.0018 (8)0.0010 (8)
C140.0197 (10)0.0243 (10)0.0275 (11)−0.0006 (8)0.0003 (9)0.0008 (8)
C150.0190 (9)0.0192 (10)0.0268 (10)−0.0002 (8)0.0040 (8)0.0004 (8)
C160.0175 (9)0.0230 (10)0.0192 (9)0.0004 (7)0.0035 (8)−0.0003 (8)
C170.0221 (10)0.0194 (10)0.0194 (10)0.0012 (8)0.0054 (8)−0.0018 (8)
C180.0319 (12)0.0327 (12)0.0228 (11)−0.0038 (10)0.0015 (9)0.0022 (9)
C190.0201 (11)0.0323 (12)0.0312 (11)−0.0001 (9)0.0060 (9)0.0026 (10)
C200.0224 (10)0.0206 (10)0.0271 (11)0.0018 (8)0.0041 (9)0.0022 (8)
C210.0252 (11)0.0282 (11)0.0249 (11)0.0024 (8)0.0059 (9)0.0046 (9)
C220.0279 (11)0.0289 (11)0.0312 (11)0.0008 (9)0.0107 (9)0.0048 (9)
C230.0360 (12)0.0247 (11)0.0233 (11)−0.0021 (9)0.0114 (9)0.0022 (8)
C240.0327 (11)0.0220 (10)0.0215 (10)0.0007 (9)0.0046 (9)−0.0004 (8)
C250.0307 (11)0.0239 (10)0.0199 (10)0.0013 (9)0.0006 (9)0.0008 (8)
C260.0238 (11)0.0269 (11)0.0294 (11)−0.0023 (9)−0.0031 (9)0.0020 (9)
C270.0231 (11)0.0282 (11)0.0319 (12)−0.0042 (9)0.0042 (9)0.0049 (9)
C280.0249 (11)0.0248 (10)0.0245 (10)−0.0002 (8)0.0039 (9)0.0027 (8)
C290.0216 (10)0.0184 (9)0.0206 (10)0.0007 (8)0.0055 (8)−0.0017 (8)
C300.0242 (10)0.0175 (9)0.0211 (10)0.0019 (8)0.0076 (8)−0.0008 (8)
C310.0271 (10)0.0167 (10)0.0191 (10)0.0021 (8)0.0053 (8)−0.0016 (7)
C320.0253 (10)0.0175 (9)0.0211 (10)0.0025 (8)0.0041 (8)−0.0027 (8)
C330.0220 (10)0.0179 (9)0.0205 (9)0.0028 (8)0.0022 (8)0.0002 (8)

Geometric parameters (Å, °)

N1—C111.270 (2)C15—C191.501 (3)
N1—C11.429 (2)C16—C171.501 (2)
C1—C21.399 (2)C16—C201.558 (3)
C1—C61.401 (2)C18—H141.02 (2)
C2—C31.397 (2)C18—H151.03 (2)
C2—C71.507 (3)C18—H161.02 (2)
C3—C41.386 (3)C19—H171.02 (2)
C3—H11.000 (19)C19—H181.02 (2)
C4—C51.393 (3)C19—H190.99 (2)
C4—C81.508 (3)C20—H201.04 (2)
C5—C61.391 (3)C20—H211.01 (2)
C5—H21.033 (19)C20—H221.03 (2)
C6—C91.504 (3)C21—C221.392 (3)
C7—H31.00 (2)C21—C301.396 (2)
C7—H41.02 (2)C21—H231.00 (2)
C7—H51.00 (2)C22—C231.392 (3)
C8—H61.02 (2)C22—H241.01 (2)
C8—H70.93 (2)C23—C241.389 (3)
C8—H80.97 (2)C23—H250.986 (19)
C9—H91.00 (2)C24—C311.387 (3)
C9—H101.02 (2)C24—H261.00 (2)
C9—H111.01 (2)C25—C321.385 (3)
N2—C171.294 (2)C25—C261.387 (3)
N2—C101.415 (2)C25—H270.970 (19)
C10—C291.367 (2)C26—C271.384 (3)
C10—C111.501 (2)C26—H280.99 (2)
C11—C161.545 (2)C27—C281.396 (3)
C12—C131.338 (3)C27—H290.969 (19)
C12—C161.506 (2)C28—C331.396 (2)
C12—H121.020 (18)C28—H301.010 (18)
C13—C141.471 (3)C29—C331.484 (2)
C13—C181.503 (3)C29—C301.493 (2)
C14—C151.351 (2)C30—C311.407 (2)
C14—H131.01 (2)C31—C321.463 (2)
C15—C171.451 (2)C32—C331.415 (2)
C11—N1—C1121.90 (15)C11—C16—C20107.90 (14)
C2—C1—C6121.03 (16)N2—C17—C15122.92 (16)
C2—C1—N1119.90 (16)N2—C17—C16115.94 (15)
C6—C1—N1118.61 (16)C15—C17—C16121.02 (15)
C3—C2—C1118.44 (17)C13—C18—H14110.5 (12)
C3—C2—C7120.75 (17)C13—C18—H15111.5 (11)
C1—C2—C7120.76 (16)H14—C18—H15108.6 (16)
C4—C3—C2121.85 (18)C13—C18—H16109.9 (11)
C4—C3—H1120.0 (10)H14—C18—H16108.2 (17)
C2—C3—H1118.1 (10)H15—C18—H16108.1 (17)
C3—C4—C5118.19 (17)C15—C19—H17110.4 (11)
C3—C4—C8121.55 (19)C15—C19—H18111.8 (11)
C5—C4—C8120.25 (18)H17—C19—H18111.0 (16)
C6—C5—C4122.15 (17)C15—C19—H19110.7 (12)
C6—C5—H2118.7 (10)H17—C19—H19109.3 (17)
C4—C5—H2119.2 (10)H18—C19—H19103.5 (16)
C5—C6—C1118.23 (17)C16—C20—H20111.0 (11)
C5—C6—C9120.84 (17)C16—C20—H21110.5 (11)
C1—C6—C9120.92 (16)H20—C20—H21110.9 (16)
C2—C7—H3113.6 (12)C16—C20—H22109.5 (11)
C2—C7—H4109.7 (11)H20—C20—H22108.9 (15)
H3—C7—H4107.3 (16)H21—C20—H22106.0 (15)
C2—C7—H5113.4 (12)C22—C21—C30119.02 (18)
H3—C7—H5105.1 (16)C22—C21—H23119.2 (11)
H4—C7—H5107.4 (16)C30—C21—H23121.8 (11)
C4—C8—H6111.4 (12)C23—C22—C21121.32 (19)
C4—C8—H7110.8 (14)C23—C22—H24119.2 (11)
H6—C8—H7106.9 (18)C21—C22—H24119.3 (11)
C4—C8—H8111.7 (13)C24—C23—C22120.05 (18)
H6—C8—H8106.2 (18)C24—C23—H25118.5 (11)
H7—C8—H8109.6 (19)C22—C23—H25121.4 (11)
C6—C9—H9112.9 (12)C31—C24—C23119.00 (18)
C6—C9—H10112.0 (11)C31—C24—H26122.0 (11)
H9—C9—H10106.7 (17)C23—C24—H26119.0 (11)
C6—C9—H11112.4 (12)C32—C25—C26119.13 (18)
H9—C9—H11105.9 (16)C32—C25—H27120.0 (11)
H10—C9—H11106.4 (17)C26—C25—H27120.8 (11)
C17—N2—C10109.04 (14)C27—C26—C25120.13 (18)
C29—C10—N2119.21 (15)C27—C26—H28118.6 (11)
C29—C10—C11132.80 (16)C25—C26—H28121.2 (11)
N2—C10—C11107.98 (14)C26—C27—C28121.43 (19)
N1—C11—C10124.19 (16)C26—C27—H29121.3 (12)
N1—C11—C16130.86 (15)C28—C27—H29117.3 (12)
C10—C11—C16104.90 (14)C33—C28—C27119.15 (18)
C13—C12—C16120.40 (16)C33—C28—H30119.2 (11)
C13—C12—H12121.6 (10)C27—C28—H30121.7 (11)
C16—C12—H12116.9 (10)C10—C29—C33131.08 (16)
C12—C13—C14120.73 (17)C10—C29—C30123.37 (16)
C12—C13—C18122.00 (17)C33—C29—C30105.36 (14)
C14—C13—C18117.24 (17)C21—C30—C31119.19 (16)
C15—C14—C13123.33 (17)C21—C30—C29132.06 (16)
C15—C14—H13118.5 (10)C31—C30—C29108.67 (15)
C13—C14—H13118.1 (10)C24—C31—C30121.41 (17)
C14—C15—C17115.99 (16)C24—C31—C32129.88 (17)
C14—C15—C19125.04 (17)C30—C31—C32108.65 (15)
C17—C15—C19118.67 (16)C25—C32—C33121.41 (17)
C17—C16—C12111.78 (15)C25—C32—C31129.88 (17)
C17—C16—C1198.91 (13)C33—C32—C31108.71 (15)
C12—C16—C11122.63 (14)C28—C33—C32118.73 (16)
C17—C16—C20108.81 (14)C28—C33—C29132.74 (16)
C12—C16—C20106.20 (14)C32—C33—C29108.50 (15)
C11—N1—C1—C2−98.5 (2)C19—C15—C17—C16164.92 (17)
C11—N1—C1—C689.2 (2)C12—C16—C17—N2−145.07 (16)
C6—C1—C2—C3−3.7 (3)C11—C16—C17—N2−14.51 (19)
N1—C1—C2—C3−175.83 (15)C20—C16—C17—N297.96 (18)
C6—C1—C2—C7173.55 (17)C12—C16—C17—C1531.1 (2)
N1—C1—C2—C71.4 (2)C11—C16—C17—C15161.68 (15)
C1—C2—C3—C41.4 (3)C20—C16—C17—C15−85.9 (2)
C7—C2—C3—C4−175.85 (17)C30—C21—C22—C23−0.6 (3)
C2—C3—C4—C50.6 (3)C21—C22—C23—C240.4 (3)
C2—C3—C4—C8179.11 (18)C22—C23—C24—C310.2 (3)
C3—C4—C5—C6−0.3 (3)C32—C25—C26—C271.1 (3)
C8—C4—C5—C6−178.86 (18)C25—C26—C27—C28−1.3 (3)
C4—C5—C6—C1−1.9 (3)C26—C27—C28—C33−0.1 (3)
C4—C5—C6—C9179.43 (18)N2—C10—C29—C33170.95 (17)
C2—C1—C6—C54.0 (3)C11—C10—C29—C33−10.7 (3)
N1—C1—C6—C5176.18 (15)N2—C10—C29—C30−3.3 (3)
C2—C1—C6—C9−177.41 (17)C11—C10—C29—C30175.04 (17)
N1—C1—C6—C9−5.2 (2)C22—C21—C30—C310.1 (3)
C17—N2—C10—C29−174.03 (16)C22—C21—C30—C29−176.18 (18)
C17—N2—C10—C117.24 (19)C10—C29—C30—C21−10.0 (3)
C1—N1—C11—C10−175.21 (16)C33—C29—C30—C21174.43 (19)
C1—N1—C11—C161.9 (3)C10—C29—C30—C31173.40 (17)
C29—C10—C11—N1−16.7 (3)C33—C29—C30—C31−2.11 (19)
N2—C10—C11—N1161.79 (16)C23—C24—C31—C30−0.7 (3)
C29—C10—C11—C16165.60 (19)C23—C24—C31—C32176.07 (18)
N2—C10—C11—C16−15.91 (18)C21—C30—C31—C240.6 (3)
C16—C12—C13—C145.7 (3)C29—C30—C31—C24177.65 (16)
C16—C12—C13—C18−172.16 (16)C21—C30—C31—C32−176.83 (16)
C12—C13—C14—C156.5 (3)C29—C30—C31—C320.2 (2)
C18—C13—C14—C15−175.49 (18)C26—C25—C32—C330.4 (3)
C13—C14—C15—C171.2 (3)C26—C25—C32—C31−179.99 (18)
C13—C14—C15—C19174.80 (18)C24—C31—C32—C255.1 (3)
C13—C12—C16—C17−22.9 (2)C30—C31—C32—C25−177.79 (19)
C13—C12—C16—C11−139.88 (18)C24—C31—C32—C33−175.26 (18)
C13—C12—C16—C2095.6 (2)C30—C31—C32—C331.9 (2)
N1—C11—C16—C17−160.50 (19)C27—C28—C33—C321.6 (3)
C10—C11—C16—C1716.99 (17)C27—C28—C33—C29−176.13 (18)
N1—C11—C16—C12−37.4 (3)C25—C32—C33—C28−1.8 (3)
C10—C11—C16—C12140.10 (16)C31—C32—C33—C28178.55 (16)
N1—C11—C16—C2086.3 (2)C25—C32—C33—C29176.49 (17)
C10—C11—C16—C20−96.19 (16)C31—C32—C33—C29−3.20 (19)
C10—N2—C17—C15−170.90 (16)C10—C29—C33—C286.1 (3)
C10—N2—C17—C165.2 (2)C30—C29—C33—C28−178.83 (19)
C14—C15—C17—N2154.85 (17)C10—C29—C33—C32−171.78 (19)
C19—C15—C17—N2−19.2 (3)C30—C29—C33—C323.26 (19)
C14—C15—C17—C16−21.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C18—H15···C24i1.03 (2)2.74 (2)3.708 (2)157.0 (15)
C19—H17···C2ii1.02 (2)2.70 (2)3.568 (2)142.7 (15)
C23—H25···C5iii0.986 (19)2.82 (2)3.591 (2)135.2 (14)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2207).

References

  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  • Döpp, D., Krüger, C., Makedakis, G. & Nour-el-Din, A. M. (1985). Chem. Ber.118, 510–525.
  • Gerlach, C. P. & Arnold, J. (1997). J. Chem. Soc. Dalton Trans. pp. 4795–4805.
  • Jacobson, R. (1998). REQAB. Version 1.1. Molecular Structure Corporation, The Woodlands, Texas, USA.
  • Miyata, O., Kimura, Y. & Naito, T. (1999). Chem. Commun. pp. 2429–2430.
  • Mizuhata, Y., Takeda, N., Sasamori, T. & Tokitoh, N. (2005). Chem. Commun. pp. 5876–5878. [PubMed]
  • Murakami, M., Ito, H. & Ito, Y. (1996). Chem. Lett.25, 7–8.
  • Rigaku (2004). CrystalClear Version 1.3.5 SP2. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shimizu, H., Hamada, K., Ozawa, M., Kataoka, T., Hori, M., Kobayashi, K. & Tada, Y. (1991). Tetrahedron Lett.32, 4359–4362.
  • Wakita, K. (2005). yadokari-XG URL: http://www.hat.hi-ho.ne.jp/k-wakita/yadokari/index.html.

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