rac-4-{(E)-[1-Cyano-1-cyclo­hexyl-2-(1H-indol-3-yl)eth­yl]imino­meth­yl}benzonitrile

Letessier, J.; Schollmeyer, D.; Detert, H.; Opatz, T.

doi:10.1107/S1600536811049841

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3435

https://doi.org/10.1107/S1600536811049841

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rac-4-{(E)-[1-Cyano-1-cyclohexyl-2-(1H-indol-3-yl)ethyl]iminomethyl}benzonitrile

Julien Letessier,^a Dieter Schollmeyer,^a Heiner Detert ^a and Till Opatz ^a ^*

^aUniversity Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
^*Correspondence e-mail: opatz@uni-mainz.de

(Received 14 November 2011; accepted 21 November 2011; online 25 November 2011)

A phosphine-catalysed addition of gramine to an alkylideneaminonitrile gives the title compound, C₂₅H₂₄N₄, in good yield. In the crystal, pairs of molecules are connected via N—H⋯N hydrogen bonds into inversion dimers. The molecules are characterized by a planar indole moiety [maximum deviation = 0.012 (1) Å], a chair conformation of the cyclohexane ring and an antiperiplanar conformation of the H atom on the cyclohexane and the adjacent cyano group.

Related literature

For related structures, see: Son et al. (2008 ); Tacheva et al. (2010 ); Bergner et al. (2009 ); Patel et al. (2011 )). For background to this work see: Dassonneville et al. (2011 ); Nissen & Detert (2011 ). For the synthesis, see: Somei et al. (1980 ). For synthetic applications of deprotonated aminonitriles, see: Opatz (2009 ); Meyer et al. (2005 ); in polysubstituted pyrroles, see: Bergner & Opatz (2007 ); in tetrahydroisoquinolines, see: Werner et al. (2007 ); Ferenc & Opatz (2008 ); Romek & Opatz (2010 ).

Experimental

Crystal data

C₂₅H₂₄N₄
M_r = 380.48
Triclinic, $[P \overline 1]$
a = 9.0755 (6) Å
b = 10.4546 (8) Å
c = 11.8246 (8) Å
α = 92.958 (6)°
β = 105.995 (5)°
γ = 99.505 (6)°
V = 1058.09 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 193 K
0.34 × 0.17 × 0.13 mm

Data collection

Stoe IPDS 2T diffractometer
11005 measured reflections
5089 independent reflections
3183 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 0.99
5089 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N13ⁱ	0.88	2.17	2.9801 (18)	152
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049841/nc2256sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049841/nc2256Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049841/nc2256Isup3.cml

checkCIF report

Comment top

The title compound was prepared as an intermediate in a new access to β-carbolines. A tributylphosphine catalyzed addition of gramine on alkylideneaminonitrile (Somei et al. (1980)) leads to the title compound (Fig. 1). The indole moiety is essentially planar (max. deviation at N1 0.012 (1) Å) and the cyclohexane ring adopts a chair conformation (Fig. 1). The hydrogen on C14 of the cyclohexane and the adjacent cyano group C12—N13 are in an anti-periplanar conformation (C12—C11—C14—H14: 178 °). Pairs of molecules form centrosymmetrical dimers (Fig. 2) connected via N1—H1···N13 hydrogen bridges (N1···N13 2.980 (2) Å) (Tab. 1).

Related literature top

For related structures, see: Son et al. (2008); Tacheva et al. (2010); Bergner et al. (2009); Patel et al. (2011)). For background to this work see: Dassonneville et al. (2011); Nissen & Detert (2011). For the synthesis, see: Somei et al. (1980). For synthetic applications, see: Opatz (2009); Meyer et al. (2005); in polysubstituted pyrroles, see: Bergner & Opatz (2007); in tetrahydroisoquinolines, see: Werner et al. (2007); Ferenc & Opatz (2008); Romek & Opatz (2010).

Experimental top

4-[(E)-{[Cyano(cyclohexyl)methyl]imino}methyl]benzonitrile (90 mg, 1.0 equiv., 0.36 mmol) and gramine (66 mg, 1.05 equiv., 0.38 mmol) were dissolved in CH₃CN (3 ml) in an argon-filled microwave reaction tube and P(Bu)₃ (36 µL, 0.40 equiv., 0.14 mmol) was added. The tube was sealed and irradiated (300 W) at 413 K for one hour (air cooling). The reaction mixture was diluted in CH₂Cl₂ (20 ml) and washed three times with sat aq. NaHCO₃ (20 ml) and brine (10 ml). The organic layer was dried over MgSO₄, filtered and the solvent was evaporated in vacuo. Purification by silica gel chromatography (petroleum ether / ethyl acetate / triethyl amine = 8 / 2 / 1) and recrystallization from petroleum ether / chloroform afforded the title compound as a pale yellow solid (104 mg, 76%).

Structure description top

For related structures, see: Son et al. (2008); Tacheva et al. (2010); Bergner et al. (2009); Patel et al. (2011)). For background to this work see: Dassonneville et al. (2011); Nissen & Detert (2011). For the synthesis, see: Somei et al. (1980). For synthetic applications, see: Opatz (2009); Meyer et al. (2005); in polysubstituted pyrroles, see: Bergner & Opatz (2007); in tetrahydroisoquinolines, see: Werner et al. (2007); Ferenc & Opatz (2008); Romek & Opatz (2010).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. View of the centrosymmetric dimers with hydrogen bonding shown as dashed lines.

rac-4-{(E)-[1-Cyano-1-cyclohexyl-2-(1H-indol- 3-yl)ethyl]iminomethyl}benzonitrile top

Crystal data top

C₂₅H₂₄N₄	Z = 2
M_r = 380.48	F(000) = 404
Triclinic, P1	D_x = 1.194 Mg m⁻³
Hall symbol: -P 1	Melting point = 438–439 K
a = 9.0755 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4546 (8) Å	Cell parameters from 7492 reflections
c = 11.8246 (8) Å	θ = 3.4–29.7°
α = 92.958 (6)°	µ = 0.07 mm⁻¹
β = 105.995 (5)°	T = 193 K
γ = 99.505 (6)°	Block, colourless
V = 1058.09 (13) Å³	0.34 × 0.17 × 0.13 mm

Data collection top

Stoe IPDS 2T diffractometer	3183 reflections with I > 2σ(I)
Radiation source: sealed Tube	R_int = 0.035
Graphite monochromator	θ_max = 28.0°, θ_min = 3.4°
Detector resolution: 6.67 pixels mm^-1	h = −11→11
rotation method scans	k = −13→13
11005 measured reflections	l = −15→15
5089 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.052P)²] where P = (F_o² + 2F_c²)/3
5089 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₅H₂₄N₄	γ = 99.505 (6)°
M_r = 380.48	V = 1058.09 (13) Å³
Triclinic, P1	Z = 2
a = 9.0755 (6) Å	Mo Kα radiation
b = 10.4546 (8) Å	µ = 0.07 mm⁻¹
c = 11.8246 (8) Å	T = 193 K
α = 92.958 (6)°	0.34 × 0.17 × 0.13 mm
β = 105.995 (5)°

Data collection top

Stoe IPDS 2T diffractometer	3183 reflections with I > 2σ(I)
11005 measured reflections	R_int = 0.035
5089 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 0.99	Δρ_max = 0.17 e Å⁻³
5089 reflections	Δρ_min = −0.23 e Å⁻³
262 parameters

Special details top

Experimental. IR (neat, ATR): ν (cm^-1) = 3411 (br), 2927 (s), 2853 (m), 2227 (m), 1921 (w), 1643 (m), 1452 (s), 1095 (w), 1069 (w), 1009 (w), 892 (w), 834 (s), 771 (w),738 (vs).

¹H-NMR (400 MHz, CDCl₃): δ = 8.05 (s, 1H, H1), 7.95 (s, 1H, H21), 7.65 (d, ³J_HH = 8.4 Hz, 2H, H23), 7.62 (d, ³J_HH = 8.4 Hz, 2H, H24), 7.44 (d, ³J_HH = 8.0 Hz, 1H, H6), 7.24 (m, 1H, H3), 7.09 (d, ⁴J_HH = 2. 4 Hz, 1H, H9), 7.04 (t, ³J_HH = 8.0 Hz, 1H, H5), 6.87 (t, ³J_HH = 7.5 Hz, 1H, H4), 3.49 (d, ²J_HH = 14.3 Hz, 1H, H10), 3.35 (d, ²J_HH = 14.3 Hz, 1H, 10-CH₂), 2.26–1.66 (m, 6H, cyclohexane), 1.46–1.13 (m, 5H, cyclohexane).

FD—MS: m/z (%) = 380.6 (100) [C₂₅H₂₄N₄] ⁺, 381.6 (29).

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	0.58172 (14)	0.16501 (12)	0.34742 (10)	0.0446 (3)
H1	0.6422	0.1093	0.3401	0.053*
C2	0.51776 (15)	0.23949 (13)	0.26196 (11)	0.0388 (3)
C3	0.52832 (18)	0.24696 (15)	0.14670 (12)	0.0486 (4)
H3	0.5864	0.1944	0.1151	0.058*
C4	0.45124 (19)	0.33346 (17)	0.08059 (12)	0.0545 (4)
H4	0.4560	0.3403	0.0018	0.065*
C5	0.36656 (18)	0.41101 (16)	0.12666 (13)	0.0523 (4)
H5	0.3155	0.4703	0.0791	0.063*
C6	0.35547 (16)	0.40333 (14)	0.24005 (12)	0.0434 (3)
H6	0.2973	0.4567	0.2706	0.052*
C7	0.43120 (15)	0.31584 (13)	0.30950 (11)	0.0356 (3)
C8	0.44490 (15)	0.28356 (12)	0.42828 (11)	0.0359 (3)
C9	0.53641 (16)	0.19104 (14)	0.44635 (12)	0.0419 (3)
H9	0.5647	0.1505	0.5172	0.050*
C10	0.37533 (15)	0.34143 (13)	0.51440 (11)	0.0391 (3)
H10A	0.3701	0.4330	0.4990	0.047*
H10B	0.4461	0.3428	0.5950	0.047*
C11	0.20943 (15)	0.26983 (12)	0.51160 (10)	0.0339 (3)
C12	0.22302 (15)	0.14187 (13)	0.55972 (11)	0.0369 (3)
N13	0.23057 (15)	0.04430 (12)	0.59751 (10)	0.0487 (3)
C14	0.13740 (15)	0.35027 (12)	0.58881 (10)	0.0346 (3)
H14	0.1336	0.4365	0.5564	0.042*
C15	−0.03045 (16)	0.28806 (14)	0.58034 (12)	0.0417 (3)
H15A	−0.0947	0.2791	0.4968	0.050*
H15B	−0.0323	0.1996	0.6067	0.050*
C16	−0.10125 (17)	0.36810 (15)	0.65522 (12)	0.0450 (3)
H16A	−0.1117	0.4526	0.6227	0.054*
H16B	−0.2069	0.3213	0.6516	0.054*
C17	−0.00124 (18)	0.39252 (14)	0.78303 (12)	0.0453 (3)
H17A	0.0015	0.3086	0.8180	0.054*
H17B	−0.0472	0.4484	0.8288	0.054*
C18	0.16384 (18)	0.45897 (15)	0.79033 (12)	0.0488 (4)
H18A	0.1614	0.5456	0.7606	0.059*
H18B	0.2283	0.4723	0.8740	0.059*
C19	0.23735 (17)	0.37809 (15)	0.71819 (11)	0.0446 (3)
H19A	0.2488	0.2946	0.7525	0.054*
H19B	0.3427	0.4255	0.7219	0.054*
N20	0.11173 (12)	0.25599 (10)	0.38904 (8)	0.0344 (2)
C21	0.06207 (15)	0.14545 (12)	0.33013 (10)	0.0365 (3)
H21	0.0836	0.0694	0.3671	0.044*
C22	−0.02917 (15)	0.13329 (13)	0.20417 (10)	0.0379 (3)
C23	−0.1016 (2)	0.01174 (15)	0.14411 (12)	0.0529 (4)
H23	−0.0948	−0.0640	0.1849	0.064*
C24	−0.1835 (2)	−0.00046 (17)	0.02578 (13)	0.0644 (5)
H24	−0.2321	−0.0841	−0.0149	0.077*
C25	−0.19417 (19)	0.10979 (17)	−0.03294 (12)	0.0561 (4)
C26	−0.12354 (17)	0.23217 (15)	0.02625 (12)	0.0478 (4)
H26	−0.1322	0.3079	−0.0144	0.057*
C27	−0.04120 (16)	0.24334 (13)	0.14366 (11)	0.0408 (3)
H27	0.0080	0.3270	0.1839	0.049*
C28	−0.2738 (3)	0.1007 (2)	−0.15794 (14)	0.0846 (7)
N29	−0.3312 (3)	0.0976 (2)	−0.25669 (14)	0.1323 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0387 (6)	0.0444 (7)	0.0524 (7)	0.0127 (5)	0.0132 (5)	0.0054 (5)
C2	0.0332 (7)	0.0404 (7)	0.0404 (7)	0.0009 (6)	0.0106 (5)	0.0017 (5)
C3	0.0439 (8)	0.0552 (9)	0.0458 (8)	−0.0023 (7)	0.0198 (6)	−0.0052 (6)
C4	0.0534 (9)	0.0698 (10)	0.0360 (7)	−0.0051 (8)	0.0149 (7)	0.0084 (7)
C5	0.0506 (9)	0.0617 (10)	0.0430 (7)	0.0064 (7)	0.0105 (7)	0.0189 (7)
C6	0.0403 (8)	0.0460 (8)	0.0446 (7)	0.0080 (6)	0.0123 (6)	0.0110 (6)
C7	0.0317 (7)	0.0382 (7)	0.0351 (6)	0.0016 (5)	0.0093 (5)	0.0049 (5)
C8	0.0332 (7)	0.0375 (7)	0.0352 (6)	0.0018 (5)	0.0091 (5)	0.0061 (5)
C9	0.0376 (7)	0.0443 (7)	0.0405 (7)	0.0043 (6)	0.0070 (6)	0.0087 (6)
C10	0.0378 (7)	0.0411 (7)	0.0349 (6)	−0.0009 (6)	0.0101 (5)	0.0015 (5)
C11	0.0352 (7)	0.0348 (6)	0.0295 (6)	0.0031 (5)	0.0069 (5)	0.0062 (5)
C12	0.0367 (7)	0.0414 (7)	0.0330 (6)	0.0072 (6)	0.0104 (5)	0.0056 (5)
N13	0.0535 (8)	0.0471 (7)	0.0502 (7)	0.0153 (6)	0.0177 (6)	0.0151 (6)
C14	0.0398 (7)	0.0337 (6)	0.0296 (6)	0.0046 (5)	0.0096 (5)	0.0061 (5)
C15	0.0402 (8)	0.0442 (7)	0.0401 (7)	0.0051 (6)	0.0127 (6)	0.0011 (6)
C16	0.0441 (8)	0.0479 (8)	0.0452 (7)	0.0085 (6)	0.0166 (6)	0.0047 (6)
C17	0.0606 (9)	0.0398 (7)	0.0425 (7)	0.0093 (7)	0.0255 (7)	0.0083 (6)
C18	0.0546 (9)	0.0541 (9)	0.0351 (7)	0.0038 (7)	0.0138 (6)	−0.0031 (6)
C19	0.0441 (8)	0.0545 (9)	0.0317 (6)	0.0059 (6)	0.0077 (6)	0.0012 (6)
N20	0.0360 (6)	0.0362 (6)	0.0297 (5)	0.0032 (4)	0.0090 (4)	0.0045 (4)
C21	0.0408 (7)	0.0348 (7)	0.0329 (6)	0.0039 (5)	0.0108 (5)	0.0047 (5)
C22	0.0393 (7)	0.0415 (7)	0.0314 (6)	0.0015 (6)	0.0116 (5)	0.0030 (5)
C23	0.0691 (10)	0.0420 (8)	0.0371 (7)	−0.0076 (7)	0.0086 (7)	0.0026 (6)
C24	0.0783 (12)	0.0567 (10)	0.0387 (8)	−0.0230 (9)	0.0068 (7)	−0.0012 (7)
C25	0.0538 (9)	0.0691 (10)	0.0324 (7)	−0.0151 (8)	0.0062 (6)	0.0066 (7)
C26	0.0488 (8)	0.0545 (9)	0.0369 (7)	0.0019 (7)	0.0103 (6)	0.0126 (6)
C27	0.0438 (8)	0.0410 (7)	0.0354 (6)	0.0025 (6)	0.0115 (6)	0.0029 (5)
C28	0.0929 (15)	0.0869 (14)	0.0417 (9)	−0.0396 (12)	−0.0022 (9)	0.0141 (8)
N29	0.163 (2)	0.1240 (16)	0.0438 (8)	−0.0756 (15)	−0.0218 (10)	0.0248 (9)

Geometric parameters (Å, º) top

N1—C2	1.3681 (17)	C15—H15A	0.9900
N1—C9	1.3715 (18)	C15—H15B	0.9900
N1—H1	0.8800	C16—C17	1.517 (2)
C2—C3	1.3976 (18)	C16—H16A	0.9900
C2—C7	1.4051 (19)	C16—H16B	0.9900
C3—C4	1.378 (2)	C17—C18	1.521 (2)
C3—H3	0.9500	C17—H17A	0.9900
C4—C5	1.391 (2)	C17—H17B	0.9900
C4—H4	0.9500	C18—C19	1.521 (2)
C5—C6	1.3773 (19)	C18—H18A	0.9900
C5—H5	0.9500	C18—H18B	0.9900
C6—C7	1.3992 (19)	C19—H19A	0.9900
C6—H6	0.9500	C19—H19B	0.9900
C7—C8	1.4382 (16)	N20—C21	1.2633 (16)
C8—C9	1.364 (2)	C21—C22	1.4786 (17)
C8—C10	1.4895 (19)	C21—H21	0.9500
C9—H9	0.9500	C22—C23	1.3875 (19)
C10—C11	1.5576 (17)	C22—C27	1.3897 (18)
C10—H10A	0.9900	C23—C24	1.380 (2)
C10—H10B	0.9900	C23—H23	0.9500
C11—N20	1.4612 (15)	C24—C25	1.379 (2)
C11—C12	1.4910 (17)	C24—H24	0.9500
C11—C14	1.5489 (18)	C25—C26	1.388 (2)
C12—N13	1.1394 (16)	C25—C28	1.446 (2)
C14—C15	1.5282 (18)	C26—C27	1.3719 (18)
C14—C19	1.5330 (17)	C26—H26	0.9500
C14—H14	1.0000	C27—H27	0.9500
C15—C16	1.520 (2)	C28—N29	1.136 (2)

C2—N1—C9	109.06 (12)	C14—C15—H15B	109.2
C2—N1—H1	125.5	H15A—C15—H15B	107.9
C9—N1—H1	125.5	C17—C16—C15	111.34 (12)
N1—C2—C3	130.63 (14)	C17—C16—H16A	109.4
N1—C2—C7	107.47 (11)	C15—C16—H16A	109.4
C3—C2—C7	121.90 (13)	C17—C16—H16B	109.4
C4—C3—C2	117.47 (15)	C15—C16—H16B	109.4
C4—C3—H3	121.3	H16A—C16—H16B	108.0
C2—C3—H3	121.3	C16—C17—C18	110.28 (11)
C3—C4—C5	121.45 (13)	C16—C17—H17A	109.6
C3—C4—H4	119.3	C18—C17—H17A	109.6
C5—C4—H4	119.3	C16—C17—H17B	109.6
C6—C5—C4	121.14 (14)	C18—C17—H17B	109.6
C6—C5—H5	119.4	H17A—C17—H17B	108.1
C4—C5—H5	119.4	C19—C18—C17	111.34 (12)
C5—C6—C7	119.02 (15)	C19—C18—H18A	109.4
C5—C6—H6	120.5	C17—C18—H18A	109.4
C7—C6—H6	120.5	C19—C18—H18B	109.4
C6—C7—C2	119.01 (12)	C17—C18—H18B	109.4
C6—C7—C8	133.73 (13)	H18A—C18—H18B	108.0
C2—C7—C8	107.25 (11)	C18—C19—C14	111.10 (12)
C9—C8—C7	106.01 (12)	C18—C19—H19A	109.4
C9—C8—C10	127.18 (11)	C14—C19—H19A	109.4
C7—C8—C10	126.80 (12)	C18—C19—H19B	109.4
C8—C9—N1	110.21 (12)	C14—C19—H19B	109.4
C8—C9—H9	124.9	H19A—C19—H19B	108.0
N1—C9—H9	124.9	C21—N20—C11	121.14 (11)
C8—C10—C11	115.35 (10)	N20—C21—C22	120.67 (12)
C8—C10—H10A	108.4	N20—C21—H21	119.7
C11—C10—H10A	108.4	C22—C21—H21	119.7
C8—C10—H10B	108.4	C23—C22—C27	119.03 (12)
C11—C10—H10B	108.4	C23—C22—C21	120.53 (12)
H10A—C10—H10B	107.5	C27—C22—C21	120.42 (12)
N20—C11—C12	112.70 (10)	C24—C23—C22	120.77 (14)
N20—C11—C14	108.71 (10)	C24—C23—H23	119.6
C12—C11—C14	108.63 (9)	C22—C23—H23	119.6
N20—C11—C10	107.39 (9)	C25—C24—C23	119.43 (14)
C12—C11—C10	108.49 (11)	C25—C24—H24	120.3
C14—C11—C10	110.94 (10)	C23—C24—H24	120.3
N13—C12—C11	178.41 (14)	C24—C25—C26	120.46 (13)
C15—C14—C19	110.85 (10)	C24—C25—C28	121.09 (15)
C15—C14—C11	112.32 (10)	C26—C25—C28	118.41 (15)
C19—C14—C11	112.82 (11)	C27—C26—C25	119.74 (13)
C15—C14—H14	106.8	C27—C26—H26	120.1
C19—C14—H14	106.8	C25—C26—H26	120.1
C11—C14—H14	106.8	C26—C27—C22	120.56 (13)
C16—C15—C14	112.13 (11)	C26—C27—H27	119.7
C16—C15—H15A	109.2	C22—C27—H27	119.7
C14—C15—H15A	109.2	N29—C28—C25	176.98 (19)
C16—C15—H15B	109.2

C9—N1—C2—C3	−179.37 (14)	C10—C11—C14—C15	175.47 (10)
C9—N1—C2—C7	0.76 (14)	N20—C11—C14—C19	−176.23 (10)
N1—C2—C3—C4	−179.33 (13)	C12—C11—C14—C19	60.80 (13)
C7—C2—C3—C4	0.5 (2)	C10—C11—C14—C19	−58.36 (13)
C2—C3—C4—C5	0.3 (2)	C19—C14—C15—C16	53.39 (15)
C3—C4—C5—C6	−0.6 (2)	C11—C14—C15—C16	−179.38 (10)
C4—C5—C6—C7	0.1 (2)	C14—C15—C16—C17	−55.08 (15)
C5—C6—C7—C2	0.72 (19)	C15—C16—C17—C18	56.49 (16)
C5—C6—C7—C8	179.62 (13)	C16—C17—C18—C19	−57.64 (16)
N1—C2—C7—C6	178.85 (11)	C17—C18—C19—C14	56.67 (15)
C3—C2—C7—C6	−1.03 (19)	C15—C14—C19—C18	−53.95 (15)
N1—C2—C7—C8	−0.32 (14)	C11—C14—C19—C18	179.09 (11)
C3—C2—C7—C8	179.79 (12)	C12—C11—N20—C21	−7.59 (17)
C6—C7—C8—C9	−179.23 (14)	C14—C11—N20—C21	−128.07 (12)
C2—C7—C8—C9	−0.23 (14)	C10—C11—N20—C21	111.83 (13)
C6—C7—C8—C10	−0.2 (2)	C11—N20—C21—C22	−176.49 (11)
C2—C7—C8—C10	178.80 (12)	N20—C21—C22—C23	−171.10 (14)
C7—C8—C9—N1	0.71 (14)	N20—C21—C22—C27	10.1 (2)
C10—C8—C9—N1	−178.32 (12)	C27—C22—C23—C24	0.6 (2)
C2—N1—C9—C8	−0.93 (15)	C21—C22—C23—C24	−178.30 (15)
C9—C8—C10—C11	−90.70 (16)	C22—C23—C24—C25	−0.5 (3)
C7—C8—C10—C11	90.47 (15)	C23—C24—C25—C26	−0.1 (3)
C8—C10—C11—N20	−51.87 (14)	C23—C24—C25—C28	177.63 (18)
C8—C10—C11—C12	70.21 (13)	C24—C25—C26—C27	0.7 (3)
C8—C10—C11—C14	−170.53 (10)	C28—C25—C26—C27	−177.12 (16)
N20—C11—C12—N13	−93 (5)	C25—C26—C27—C22	−0.6 (2)
C14—C11—C12—N13	27 (5)	C23—C22—C27—C26	0.0 (2)
C10—C11—C12—N13	148 (5)	C21—C22—C27—C26	178.88 (13)
N20—C11—C14—C15	57.61 (12)	C24—C25—C28—N29	−137 (6)
C12—C11—C14—C15	−65.36 (13)	C26—C25—C28—N29	41 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N13ⁱ	0.88	2.17	2.9801 (18)	152

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₄N₄
M_r	380.48
Crystal system, space group	Triclinic, P1
Temperature (K)	193
a, b, c (Å)	9.0755 (6), 10.4546 (8), 11.8246 (8)
α, β, γ (°)	92.958 (6), 105.995 (5), 99.505 (6)
V (Å³)	1058.09 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.34 × 0.17 × 0.13

Data collection
Diffractometer	Stoe IPDS 2T
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11005, 5089, 3183
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 0.99
No. of reflections	5089
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

Computer programs: X-AREA (Stoe & Cie, 2001), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N13ⁱ	0.88	2.17	2.9801 (18)	152

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The authors are grateful to Heinz Kolshorn for the NMR spectroscopy and helpful discussions.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Son, Y.-A., Matsumoto, S., Han, E.-M., Wang, S. & Kim, S.-H. (2008). Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 492, 46–52. Web of Science CrossRef CAS Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

rac-4-{(E)-[1-Cyano-1-cyclo­hexyl-2-(1H-indol-3-yl)eth­yl]imino­meth­yl}benzo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-4-{(E)-[1-Cyano-1-cyclohexyl-2-(1H-indol-3-yl)ethyl]iminomethyl}benzonitrile