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

Mizuhata, Y.; Tokitoh, N.

doi:10.1107/S1600536808001657

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o493

doi:10.1107/S1600536808001657

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

Yoshiyuki Mizuhata ^a and Norihiro Tokitoh ^a ^*

^aInstitute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
^*Correspondence e-mail: tokitoh@boc.kuicr.kyoto-u.ac.jp

(Received 4 January 2008; accepted 16 January 2008; online 23 January 2008)

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 ); Gerlach & Arnold (1997 ); Miyata et al. (1999 ); Mizuhata et al. (2005 ); Murakami et al. (1996 ); Shimizu et al. (1991 ).

Experimental

Crystal data

C₃₃H₃₀N₂
M_r = 454.59
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.096
S = 1.02
4289 reflections
407 parameters
Only H-atom coordinates refined
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H15⋯C24ⁱ	1.03 (2)	2.74 (2)	3.708 (2)	157.0 (15)
C19—H17⋯C2ⁱⁱ	1.02 (2)	2.70 (2)	3.568 (2)	142.7 (15)
C23—H25⋯C5ⁱⁱⁱ	0.986 (19)	2.82 (2)	3.591 (2)	135.2 (14)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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).

Computing details top

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

Figures top

	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].

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

Crystal data top

C₃₃H₃₀N₂	F(000) = 968
M_r = 454.59	D_x = 1.233 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 411 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71069 Å
a = 10.2810 (2) Å	θ = 3.4–25.0°
b = 11.2727 (3) Å	µ = 0.07 mm⁻¹
c = 21.6598 (5) Å	T = 103 K
β = 102.5953 (16)°	Prism, red
V = 2449.84 (10) Å³	0.20 × 0.20 × 0.05 mm
Z = 4

Data collection top

Rigaku Mercury CCD diffractometer	2994 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
ω scans	θ_max = 25.0°, θ_min = 3.4°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −12→12
T_min = 0.986, T_max = 0.996	k = −13→10
15962 measured reflections	l = −24→25
4289 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	Only H-atom coordinates refined
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0373P)² + 0.5999P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4289 reflections	Δρ_max = 0.25 e Å⁻³
407 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (6)

Crystal data top

C₃₃H₃₀N₂	V = 2449.84 (10) Å³
M_r = 454.59	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.2810 (2) Å	µ = 0.07 mm⁻¹
b = 11.2727 (3) Å	T = 103 K
c = 21.6598 (5) Å	0.20 × 0.20 × 0.05 mm
β = 102.5953 (16)°

Data collection top

Rigaku Mercury CCD diffractometer	4289 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2994 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.996	R_int = 0.048
15962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.096	Only H-atom coordinates refined
S = 1.02	Δρ_max = 0.25 e Å⁻³
4289 reflections	Δρ_min = −0.19 e Å⁻³
407 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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*
C9	0.0248 (2)	0.19139 (18)	0.32799 (10)	0.0284 (5)
H9	0.123 (2)	0.1829 (18)	0.3322 (9)	0.043*
H10	0.012 (2)	0.2472 (19)	0.3629 (10)	0.043*
H11	−0.009 (2)	0.2346 (19)	0.2868 (10)	0.043*
N2	0.26870 (14)	0.06119 (13)	0.16733 (7)	0.0210 (3)
C10	0.12774 (17)	0.06370 (15)	0.15398 (8)	0.0202 (4)
C11	0.08304 (17)	0.01780 (15)	0.21100 (8)	0.0195 (4)
C12	0.24414 (18)	−0.03646 (16)	0.32202 (8)	0.0219 (4)
H12	0.1716 (18)	−0.0559 (16)	0.3459 (8)	0.026*
C13	0.37190 (18)	−0.02512 (16)	0.35192 (8)	0.0228 (4)
C14	0.47680 (18)	−0.00966 (16)	0.31602 (9)	0.0246 (4)
H13	0.572 (2)	−0.0065 (16)	0.3402 (9)	0.030*
C15	0.45125 (17)	0.00537 (15)	0.25265 (9)	0.0218 (4)
C16	0.20669 (17)	−0.04503 (16)	0.25098 (8)	0.0200 (4)
C17	0.31158 (17)	0.00802 (15)	0.22083 (8)	0.0202 (4)
C18	0.4151 (2)	−0.03166 (19)	0.42276 (9)	0.0298 (5)
H14	0.335 (2)	−0.0437 (19)	0.4425 (10)	0.045*
H15	0.464 (2)	0.0443 (19)	0.4412 (10)	0.045*
H16	0.479 (2)	−0.102 (2)	0.4354 (9)	0.045*
C19	0.55426 (19)	0.0312 (2)	0.21488 (10)	0.0278 (5)
H17	0.647 (2)	0.0295 (18)	0.2433 (10)	0.042*
H18	0.537 (2)	0.110 (2)	0.1915 (9)	0.042*
H19	0.549 (2)	−0.0275 (19)	0.1806 (10)	0.042*
C20	0.1947 (2)	−0.17994 (16)	0.23507 (9)	0.0235 (4)
H20	0.1700 (19)	−0.1935 (17)	0.1864 (10)	0.035*
H21	0.127 (2)	−0.2187 (17)	0.2562 (9)	0.035*
H22	0.284 (2)	−0.2210 (18)	0.2533 (9)	0.035*
C21	0.25981 (19)	0.18750 (17)	0.05033 (9)	0.0261 (5)
H23	0.3320 (19)	0.1725 (17)	0.0886 (9)	0.031*
C22	0.2922 (2)	0.24009 (18)	−0.00252 (9)	0.0287 (5)
H24	0.387 (2)	0.2675 (17)	−0.0003 (9)	0.034*
C23	0.1956 (2)	0.26124 (17)	−0.05731 (9)	0.0273 (5)
H25	0.2183 (19)	0.2987 (17)	−0.0947 (9)	0.033*
C24	0.0637 (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*
C29	0.06016 (17)	0.10611 (16)	0.09684 (8)	0.0201 (4)
C30	0.12739 (18)	0.15654 (15)	0.04819 (8)	0.0205 (4)
C31	0.03035 (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) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0207 (8)	0.0246 (9)	0.0202 (8)	0.0006 (7)	0.0055 (7)	0.0002 (7)
C1	0.0153 (9)	0.0266 (10)	0.0188 (10)	0.0045 (8)	0.0039 (8)	0.0037 (8)
C2	0.0159 (9)	0.0228 (10)	0.0225 (10)	0.0027 (8)	0.0027 (8)	0.0005 (8)
C3	0.0194 (10)	0.0238 (10)	0.0282 (11)	0.0026 (8)	0.0066 (8)	0.0034 (9)
C4	0.0187 (10)	0.0302 (11)	0.0259 (10)	0.0051 (8)	0.0084 (8)	0.0035 (9)
C5	0.0191 (10)	0.0311 (11)	0.0222 (10)	0.0041 (8)	0.0048 (8)	−0.0026 (9)
C6	0.0144 (9)	0.0250 (10)	0.0249 (10)	0.0027 (7)	0.0040 (8)	−0.0009 (8)
C7	0.0235 (11)	0.0276 (11)	0.0269 (11)	−0.0028 (9)	0.0030 (9)	−0.0026 (9)
C8	0.0338 (13)	0.0398 (13)	0.0313 (12)	0.0034 (10)	0.0136 (10)	0.0056 (10)
C9	0.0270 (11)	0.0265 (11)	0.0329 (12)	−0.0024 (9)	0.0090 (10)	−0.0051 (9)
N2	0.0184 (8)	0.0226 (8)	0.0222 (8)	0.0006 (7)	0.0046 (7)	0.0005 (7)
C10	0.0198 (9)	0.0196 (9)	0.0221 (10)	0.0010 (8)	0.0065 (8)	−0.0003 (8)
C11	0.0197 (10)	0.0197 (9)	0.0188 (9)	−0.0005 (7)	0.0035 (8)	−0.0025 (8)
C12	0.0231 (10)	0.0227 (10)	0.0203 (10)	0.0029 (8)	0.0054 (8)	0.0010 (8)
C13	0.0239 (10)	0.0219 (10)	0.0213 (10)	0.0021 (8)	0.0018 (8)	0.0010 (8)
C14	0.0197 (10)	0.0243 (10)	0.0275 (11)	−0.0006 (8)	0.0003 (9)	0.0008 (8)
C15	0.0190 (9)	0.0192 (10)	0.0268 (10)	−0.0002 (8)	0.0040 (8)	0.0004 (8)
C16	0.0175 (9)	0.0230 (10)	0.0192 (9)	0.0004 (7)	0.0035 (8)	−0.0003 (8)
C17	0.0221 (10)	0.0194 (10)	0.0194 (10)	0.0012 (8)	0.0054 (8)	−0.0018 (8)
C18	0.0319 (12)	0.0327 (12)	0.0228 (11)	−0.0038 (10)	0.0015 (9)	0.0022 (9)
C19	0.0201 (11)	0.0323 (12)	0.0312 (11)	−0.0001 (9)	0.0060 (9)	0.0026 (10)
C20	0.0224 (10)	0.0206 (10)	0.0271 (11)	0.0018 (8)	0.0041 (9)	0.0022 (8)
C21	0.0252 (11)	0.0282 (11)	0.0249 (11)	0.0024 (8)	0.0059 (9)	0.0046 (9)
C22	0.0279 (11)	0.0289 (11)	0.0312 (11)	0.0008 (9)	0.0107 (9)	0.0048 (9)
C23	0.0360 (12)	0.0247 (11)	0.0233 (11)	−0.0021 (9)	0.0114 (9)	0.0022 (8)
C24	0.0327 (11)	0.0220 (10)	0.0215 (10)	0.0007 (9)	0.0046 (9)	−0.0004 (8)
C25	0.0307 (11)	0.0239 (10)	0.0199 (10)	0.0013 (9)	0.0006 (9)	0.0008 (8)
C26	0.0238 (11)	0.0269 (11)	0.0294 (11)	−0.0023 (9)	−0.0031 (9)	0.0020 (9)
C27	0.0231 (11)	0.0282 (11)	0.0319 (12)	−0.0042 (9)	0.0042 (9)	0.0049 (9)
C28	0.0249 (11)	0.0248 (10)	0.0245 (10)	−0.0002 (8)	0.0039 (9)	0.0027 (8)
C29	0.0216 (10)	0.0184 (9)	0.0206 (10)	0.0007 (8)	0.0055 (8)	−0.0017 (8)
C30	0.0242 (10)	0.0175 (9)	0.0211 (10)	0.0019 (8)	0.0076 (8)	−0.0008 (8)
C31	0.0271 (10)	0.0167 (10)	0.0191 (10)	0.0021 (8)	0.0053 (8)	−0.0016 (7)
C32	0.0253 (10)	0.0175 (9)	0.0211 (10)	0.0025 (8)	0.0041 (8)	−0.0027 (8)
C33	0.0220 (10)	0.0179 (9)	0.0205 (9)	0.0028 (8)	0.0022 (8)	0.0002 (8)

Geometric parameters (Å, º) top

N1—C11	1.270 (2)	C15—C19	1.501 (3)
N1—C1	1.429 (2)	C16—C17	1.501 (2)
C1—C2	1.399 (2)	C16—C20	1.558 (3)
C1—C6	1.401 (2)	C18—H14	1.02 (2)
C2—C3	1.397 (2)	C18—H15	1.03 (2)
C2—C7	1.507 (3)	C18—H16	1.02 (2)
C3—C4	1.386 (3)	C19—H17	1.02 (2)
C3—H1	1.000 (19)	C19—H18	1.02 (2)
C4—C5	1.393 (3)	C19—H19	0.99 (2)
C4—C8	1.508 (3)	C20—H20	1.04 (2)
C5—C6	1.391 (3)	C20—H21	1.01 (2)
C5—H2	1.033 (19)	C20—H22	1.03 (2)
C6—C9	1.504 (3)	C21—C22	1.392 (3)
C7—H3	1.00 (2)	C21—C30	1.396 (2)
C7—H4	1.02 (2)	C21—H23	1.00 (2)
C7—H5	1.00 (2)	C22—C23	1.392 (3)
C8—H6	1.02 (2)	C22—H24	1.01 (2)
C8—H7	0.93 (2)	C23—C24	1.389 (3)
C8—H8	0.97 (2)	C23—H25	0.986 (19)
C9—H9	1.00 (2)	C24—C31	1.387 (3)
C9—H10	1.02 (2)	C24—H26	1.00 (2)
C9—H11	1.01 (2)	C25—C32	1.385 (3)
N2—C17	1.294 (2)	C25—C26	1.387 (3)
N2—C10	1.415 (2)	C25—H27	0.970 (19)
C10—C29	1.367 (2)	C26—C27	1.384 (3)
C10—C11	1.501 (2)	C26—H28	0.99 (2)
C11—C16	1.545 (2)	C27—C28	1.396 (3)
C12—C13	1.338 (3)	C27—H29	0.969 (19)
C12—C16	1.506 (2)	C28—C33	1.396 (2)
C12—H12	1.020 (18)	C28—H30	1.010 (18)
C13—C14	1.471 (3)	C29—C33	1.484 (2)
C13—C18	1.503 (3)	C29—C30	1.493 (2)
C14—C15	1.351 (2)	C30—C31	1.407 (2)
C14—H13	1.01 (2)	C31—C32	1.463 (2)
C15—C17	1.451 (2)	C32—C33	1.415 (2)

C11—N1—C1	121.90 (15)	C11—C16—C20	107.90 (14)
C2—C1—C6	121.03 (16)	N2—C17—C15	122.92 (16)
C2—C1—N1	119.90 (16)	N2—C17—C16	115.94 (15)
C6—C1—N1	118.61 (16)	C15—C17—C16	121.02 (15)
C3—C2—C1	118.44 (17)	C13—C18—H14	110.5 (12)
C3—C2—C7	120.75 (17)	C13—C18—H15	111.5 (11)
C1—C2—C7	120.76 (16)	H14—C18—H15	108.6 (16)
C4—C3—C2	121.85 (18)	C13—C18—H16	109.9 (11)
C4—C3—H1	120.0 (10)	H14—C18—H16	108.2 (17)
C2—C3—H1	118.1 (10)	H15—C18—H16	108.1 (17)
C3—C4—C5	118.19 (17)	C15—C19—H17	110.4 (11)
C3—C4—C8	121.55 (19)	C15—C19—H18	111.8 (11)
C5—C4—C8	120.25 (18)	H17—C19—H18	111.0 (16)
C6—C5—C4	122.15 (17)	C15—C19—H19	110.7 (12)
C6—C5—H2	118.7 (10)	H17—C19—H19	109.3 (17)
C4—C5—H2	119.2 (10)	H18—C19—H19	103.5 (16)
C5—C6—C1	118.23 (17)	C16—C20—H20	111.0 (11)
C5—C6—C9	120.84 (17)	C16—C20—H21	110.5 (11)
C1—C6—C9	120.92 (16)	H20—C20—H21	110.9 (16)
C2—C7—H3	113.6 (12)	C16—C20—H22	109.5 (11)
C2—C7—H4	109.7 (11)	H20—C20—H22	108.9 (15)
H3—C7—H4	107.3 (16)	H21—C20—H22	106.0 (15)
C2—C7—H5	113.4 (12)	C22—C21—C30	119.02 (18)
H3—C7—H5	105.1 (16)	C22—C21—H23	119.2 (11)
H4—C7—H5	107.4 (16)	C30—C21—H23	121.8 (11)
C4—C8—H6	111.4 (12)	C23—C22—C21	121.32 (19)
C4—C8—H7	110.8 (14)	C23—C22—H24	119.2 (11)
H6—C8—H7	106.9 (18)	C21—C22—H24	119.3 (11)
C4—C8—H8	111.7 (13)	C24—C23—C22	120.05 (18)
H6—C8—H8	106.2 (18)	C24—C23—H25	118.5 (11)
H7—C8—H8	109.6 (19)	C22—C23—H25	121.4 (11)
C6—C9—H9	112.9 (12)	C31—C24—C23	119.00 (18)
C6—C9—H10	112.0 (11)	C31—C24—H26	122.0 (11)
H9—C9—H10	106.7 (17)	C23—C24—H26	119.0 (11)
C6—C9—H11	112.4 (12)	C32—C25—C26	119.13 (18)
H9—C9—H11	105.9 (16)	C32—C25—H27	120.0 (11)
H10—C9—H11	106.4 (17)	C26—C25—H27	120.8 (11)
C17—N2—C10	109.04 (14)	C27—C26—C25	120.13 (18)
C29—C10—N2	119.21 (15)	C27—C26—H28	118.6 (11)
C29—C10—C11	132.80 (16)	C25—C26—H28	121.2 (11)
N2—C10—C11	107.98 (14)	C26—C27—C28	121.43 (19)
N1—C11—C10	124.19 (16)	C26—C27—H29	121.3 (12)
N1—C11—C16	130.86 (15)	C28—C27—H29	117.3 (12)
C10—C11—C16	104.90 (14)	C33—C28—C27	119.15 (18)
C13—C12—C16	120.40 (16)	C33—C28—H30	119.2 (11)
C13—C12—H12	121.6 (10)	C27—C28—H30	121.7 (11)
C16—C12—H12	116.9 (10)	C10—C29—C33	131.08 (16)
C12—C13—C14	120.73 (17)	C10—C29—C30	123.37 (16)
C12—C13—C18	122.00 (17)	C33—C29—C30	105.36 (14)
C14—C13—C18	117.24 (17)	C21—C30—C31	119.19 (16)
C15—C14—C13	123.33 (17)	C21—C30—C29	132.06 (16)
C15—C14—H13	118.5 (10)	C31—C30—C29	108.67 (15)
C13—C14—H13	118.1 (10)	C24—C31—C30	121.41 (17)
C14—C15—C17	115.99 (16)	C24—C31—C32	129.88 (17)
C14—C15—C19	125.04 (17)	C30—C31—C32	108.65 (15)
C17—C15—C19	118.67 (16)	C25—C32—C33	121.41 (17)
C17—C16—C12	111.78 (15)	C25—C32—C31	129.88 (17)
C17—C16—C11	98.91 (13)	C33—C32—C31	108.71 (15)
C12—C16—C11	122.63 (14)	C28—C33—C32	118.73 (16)
C17—C16—C20	108.81 (14)	C28—C33—C29	132.74 (16)
C12—C16—C20	106.20 (14)	C32—C33—C29	108.50 (15)

C11—N1—C1—C2	−98.5 (2)	C19—C15—C17—C16	164.92 (17)
C11—N1—C1—C6	89.2 (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—N2	97.96 (18)
C6—C1—C2—C7	173.55 (17)	C12—C16—C17—C15	31.1 (2)
N1—C1—C2—C7	1.4 (2)	C11—C16—C17—C15	161.68 (15)
C1—C2—C3—C4	1.4 (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—C5	0.6 (3)	C21—C22—C23—C24	0.4 (3)
C2—C3—C4—C8	179.11 (18)	C22—C23—C24—C31	0.2 (3)
C3—C4—C5—C6	−0.3 (3)	C32—C25—C26—C27	1.1 (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—C9	179.43 (18)	N2—C10—C29—C33	170.95 (17)
C2—C1—C6—C5	4.0 (3)	C11—C10—C29—C33	−10.7 (3)
N1—C1—C6—C5	176.18 (15)	N2—C10—C29—C30	−3.3 (3)
C2—C1—C6—C9	−177.41 (17)	C11—C10—C29—C30	175.04 (17)
N1—C1—C6—C9	−5.2 (2)	C22—C21—C30—C31	0.1 (3)
C17—N2—C10—C29	−174.03 (16)	C22—C21—C30—C29	−176.18 (18)
C17—N2—C10—C11	7.24 (19)	C10—C29—C30—C21	−10.0 (3)
C1—N1—C11—C10	−175.21 (16)	C33—C29—C30—C21	174.43 (19)
C1—N1—C11—C16	1.9 (3)	C10—C29—C30—C31	173.40 (17)
C29—C10—C11—N1	−16.7 (3)	C33—C29—C30—C31	−2.11 (19)
N2—C10—C11—N1	161.79 (16)	C23—C24—C31—C30	−0.7 (3)
C29—C10—C11—C16	165.60 (19)	C23—C24—C31—C32	176.07 (18)
N2—C10—C11—C16	−15.91 (18)	C21—C30—C31—C24	0.6 (3)
C16—C12—C13—C14	5.7 (3)	C29—C30—C31—C24	177.65 (16)
C16—C12—C13—C18	−172.16 (16)	C21—C30—C31—C32	−176.83 (16)
C12—C13—C14—C15	6.5 (3)	C29—C30—C31—C32	0.2 (2)
C18—C13—C14—C15	−175.49 (18)	C26—C25—C32—C33	0.4 (3)
C13—C14—C15—C17	1.2 (3)	C26—C25—C32—C31	−179.99 (18)
C13—C14—C15—C19	174.80 (18)	C24—C31—C32—C25	5.1 (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—C20	95.6 (2)	C30—C31—C32—C33	1.9 (2)
N1—C11—C16—C17	−160.50 (19)	C27—C28—C33—C32	1.6 (3)
C10—C11—C16—C17	16.99 (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—C12	140.10 (16)	C31—C32—C33—C28	178.55 (16)
N1—C11—C16—C20	86.3 (2)	C25—C32—C33—C29	176.49 (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—C28	6.1 (3)
C10—N2—C17—C16	5.2 (2)	C30—C29—C33—C28	−178.83 (19)
C14—C15—C17—N2	154.85 (17)	C10—C29—C33—C32	−171.78 (19)
C19—C15—C17—N2	−19.2 (3)	C30—C29—C33—C32	3.26 (19)
C14—C15—C17—C16	−21.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H15···C24ⁱ	1.03 (2)	2.74 (2)	3.708 (2)	157.0 (15)
C19—H17···C2ⁱⁱ	1.02 (2)	2.70 (2)	3.568 (2)	142.7 (15)
C23—H25···C5ⁱⁱⁱ	0.986 (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.

Experimental details

Crystal data
Chemical formula	C₃₃H₃₀N₂
M_r	454.59
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	103
a, b, c (Å)	10.2810 (2), 11.2727 (3), 21.6598 (5)
β (°)	102.5953 (16)
V (Å³)	2449.84 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.20 × 0.05

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.986, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	15962, 4289, 2994
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.096, 1.02
No. of reflections	4289
No. of parameters	407
H-atom treatment	Only H-atom coordinates refined
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19

Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), yadokari-XG (Wakita, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H15···C24ⁱ	1.03 (2)	2.74 (2)	3.708 (2)	157.0 (15)
C19—H17···C2ⁱⁱ	1.02 (2)	2.70 (2)	3.568 (2)	142.7 (15)
C23—H25···C5ⁱⁱⁱ	0.986 (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.

Acknowledgements

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.

References

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

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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