(Z)-4-[3-(3-Oxoquinuclidin-2-ylidene-meth-yl)-1H-indol-1-ylmeth-yl]benzo-nitrile.

The title compound, C(24)H(21)N(3)O, was prepared by the reaction of (Z)-2-(1H-indol-3-ylmethyl-ene)-1-aza-bicyclo-[2.2.2]octan-3-one with α-bromo-p-toluonitrile, under phase-transfer catalytic (PTC) conditions using triethyl-benzyl-ammonium chloride and 50% w/v aqueous NaOH solution in dichloro-methane. The crystal structure indicates the presence of a double bond with Z geometry connecting the aza-bicyclic and indole groups.

Related literature

For related structures, see: Mason et al. (2003 ▶); Zarza et al. (1988 ▶). For related bond angles, see: Wilson (1992 ▶). For related literature, see: Sekhar et al. (2003 ▶); Sonar et al. (2007 ▶).

Experimental

Crystal data

C24H21N3O

M = 367.44

Triclinic,

a = 9.0627 (2) Å

b = 10.7959 (3) Å

c = 11.6969 (4) Å

α = 99.1571 (13)°

β = 106.0935 (14)°

γ = 113.7908 (14)°

V = 957.16 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 90.0 (2) K

0.44 × 0.40 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.966, T max = 0.980

20970 measured reflections

4385 independent reflections

2935 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.128

S = 1.04

4385 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELX97 and local procedures.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030006/om2261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030006/om2261Isup2.hkl

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

C24H21N3O	Z = 2
Mr = 367.44	F(000) = 388
Triclinic, P1	Dx = 1.275 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0627 (2) Å	Cell parameters from 4341 reflections
b = 10.7959 (3) Å	θ = 1.0–27.5°
c = 11.6969 (4) Å	µ = 0.08 mm−1
α = 99.1571 (13)°	T = 90 K
β = 106.0935 (14)°	Irregular block, colourless
γ = 113.7908 (14)°	0.44 × 0.40 × 0.25 mm
V = 957.16 (5) Å3

Nonius KappaCCD diffractometer	4385 independent reflections
Radiation source: fine-focus sealed tube	2935 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 18 pixels mm-1	θmax = 27.5°, θmin = 1.9°
ω scans at fixed χ = 55°	h = −11→11
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −14→13
Tmin = 0.966, Tmax = 0.980	l = 0→15
20970 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.0538P] where P = (Fo2 + 2Fc2)/3
4385 reflections	(Δ/σ)max = 0.004
253 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
N1	0.63840 (16)	0.43150 (13)	0.54539 (11)	0.0220 (3)
N2	0.29373 (16)	0.01430 (13)	0.25488 (12)	0.0241 (3)
N3	1.56395 (18)	0.85155 (14)	1.00029 (13)	0.0306 (3)
O1	0.00836 (14)	−0.22274 (12)	0.37598 (11)	0.0320 (3)
C2	0.53780 (19)	0.29481 (16)	0.46742 (15)	0.0243 (4)
H2	0.5404	0.2614	0.3882	0.029*
C3	0.43160 (19)	0.21170 (16)	0.51985 (14)	0.0228 (3)
C4	0.47183 (19)	0.30524 (16)	0.63990 (14)	0.0215 (3)
C5	0.4079 (2)	0.28731 (16)	0.73508 (15)	0.0251 (4)
H5	0.3221	0.1967	0.7294	0.030*
C6	0.4719 (2)	0.40387 (17)	0.83761 (15)	0.0287 (4)
H6	0.4307	0.3925	0.9036	0.034*
C7	0.5965 (2)	0.53862 (17)	0.84652 (16)	0.0296 (4)
H7	0.6366	0.6171	0.9177	0.036*
C8	0.6620 (2)	0.55952 (16)	0.75394 (15)	0.0258 (4)
H8	0.7465	0.6508	0.7598	0.031*
C9	0.59912 (19)	0.44119 (16)	0.65166 (14)	0.0221 (3)
C10	0.29595 (19)	0.06574 (15)	0.46778 (15)	0.0237 (4)
H10	0.2459	0.0273	0.5236	0.028*
C11	0.23045 (19)	−0.02341 (15)	0.35161 (14)	0.0225 (3)
C12	0.1480 (2)	0.00383 (16)	0.15034 (15)	0.0266 (4)
H12A	0.1881	0.0271	0.0822	0.032*
H12B	0.1124	0.0744	0.1797	0.032*
C13	−0.0109 (2)	−0.14677 (17)	0.09871 (16)	0.0301 (4)
H13A	−0.1140	−0.1411	0.1069	0.036*
H13B	−0.0382	−0.1885	0.0090	0.036*
C14	0.03321 (19)	−0.24051 (16)	0.17351 (15)	0.0259 (4)
H14	−0.0676	−0.3383	0.1441	0.031*
C15	0.1944 (2)	−0.24547 (17)	0.15857 (16)	0.0303 (4)
H15A	0.1687	−0.2881	0.0694	0.036*
H15B	0.2270	−0.3043	0.2066	0.036*
C16	0.3455 (2)	−0.09142 (16)	0.20803 (15)	0.0280 (4)
H16A	0.4442	−0.0848	0.2765	0.034*
H16B	0.3857	−0.0684	0.1399	0.034*
C17	0.0820 (2)	−0.16865 (16)	0.30955 (15)	0.0249 (4)
C18	0.76263 (19)	0.55154 (16)	0.52187 (14)	0.0235 (3)
H18A	0.7227	0.6243	0.5193	0.028*
H18B	0.7662	0.5186	0.4392	0.028*
C19	0.94360 (19)	0.61802 (15)	0.62085 (14)	0.0222 (3)
C20	1.04167 (19)	0.76546 (16)	0.67051 (15)	0.0264 (4)
H20	0.9969	0.8237	0.6379	0.032*
C21	1.2034 (2)	0.82836 (17)	0.76673 (15)	0.0284 (4)
H21	1.2684	0.9290	0.8012	0.034*
C22	1.26979 (19)	0.74218 (16)	0.81242 (14)	0.0238 (4)
C23	1.1756 (2)	0.59485 (16)	0.76076 (15)	0.0257 (4)
H23	1.2224	0.5365	0.7905	0.031*
C24	1.0130 (2)	0.53398 (16)	0.66567 (15)	0.0256 (4)
H24	0.9482	0.4334	0.6307	0.031*
C25	1.4347 (2)	0.80457 (16)	0.91607 (15)	0.0251 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0188 (6)	0.0228 (7)	0.0201 (7)	0.0072 (6)	0.0063 (5)	0.0052 (6)
N2	0.0228 (7)	0.0244 (7)	0.0227 (7)	0.0105 (6)	0.0066 (6)	0.0063 (6)
N3	0.0275 (8)	0.0302 (8)	0.0286 (8)	0.0114 (6)	0.0075 (7)	0.0067 (6)
O1	0.0327 (7)	0.0271 (6)	0.0347 (7)	0.0098 (5)	0.0162 (6)	0.0113 (5)
C2	0.0227 (8)	0.0239 (8)	0.0208 (8)	0.0099 (7)	0.0046 (7)	0.0026 (7)
C3	0.0214 (8)	0.0241 (8)	0.0208 (8)	0.0111 (7)	0.0055 (7)	0.0052 (7)
C4	0.0190 (8)	0.0230 (8)	0.0211 (8)	0.0108 (7)	0.0043 (6)	0.0068 (7)
C5	0.0222 (8)	0.0252 (9)	0.0251 (9)	0.0091 (7)	0.0081 (7)	0.0079 (7)
C6	0.0281 (9)	0.0324 (9)	0.0242 (9)	0.0123 (8)	0.0119 (7)	0.0069 (7)
C7	0.0298 (9)	0.0288 (9)	0.0255 (9)	0.0116 (8)	0.0106 (8)	0.0022 (7)
C8	0.0231 (8)	0.0230 (8)	0.0249 (9)	0.0081 (7)	0.0060 (7)	0.0046 (7)
C9	0.0199 (8)	0.0248 (8)	0.0199 (8)	0.0108 (7)	0.0051 (6)	0.0059 (7)
C10	0.0245 (8)	0.0229 (8)	0.0250 (9)	0.0117 (7)	0.0092 (7)	0.0091 (7)
C11	0.0214 (8)	0.0207 (8)	0.0243 (9)	0.0094 (7)	0.0075 (7)	0.0075 (7)
C12	0.0262 (9)	0.0262 (9)	0.0245 (9)	0.0114 (7)	0.0067 (7)	0.0082 (7)
C13	0.0244 (9)	0.0304 (9)	0.0287 (9)	0.0106 (7)	0.0041 (7)	0.0092 (7)
C14	0.0210 (8)	0.0187 (8)	0.0273 (9)	0.0043 (7)	0.0036 (7)	0.0044 (7)
C15	0.0324 (9)	0.0269 (9)	0.0300 (10)	0.0148 (8)	0.0100 (8)	0.0060 (7)
C16	0.0260 (9)	0.0296 (9)	0.0286 (9)	0.0139 (7)	0.0101 (7)	0.0074 (7)
C17	0.0229 (8)	0.0238 (8)	0.0300 (9)	0.0129 (7)	0.0090 (7)	0.0105 (7)
C18	0.0207 (8)	0.0240 (8)	0.0230 (8)	0.0081 (7)	0.0078 (7)	0.0082 (7)
C19	0.0215 (8)	0.0232 (8)	0.0210 (8)	0.0083 (7)	0.0104 (7)	0.0068 (7)
C20	0.0243 (8)	0.0239 (9)	0.0293 (9)	0.0108 (7)	0.0077 (7)	0.0101 (7)
C21	0.0243 (9)	0.0198 (8)	0.0318 (10)	0.0060 (7)	0.0068 (7)	0.0040 (7)
C22	0.0208 (8)	0.0272 (9)	0.0222 (8)	0.0104 (7)	0.0084 (7)	0.0068 (7)
C23	0.0247 (9)	0.0252 (9)	0.0285 (9)	0.0128 (7)	0.0091 (7)	0.0105 (7)
C24	0.0242 (8)	0.0223 (8)	0.0256 (9)	0.0084 (7)	0.0081 (7)	0.0049 (7)
C25	0.0251 (9)	0.0241 (9)	0.0270 (9)	0.0109 (7)	0.0115 (8)	0.0090 (7)

N1—C2	1.3659 (19)	C12—H12B	0.9900
N1—C9	1.3845 (19)	C13—C14	1.537 (2)
N1—C18	1.4597 (18)	C13—H13A	0.9900
N2—C11	1.4466 (19)	C13—H13B	0.9900
N2—C12	1.4804 (19)	C14—C17	1.507 (2)
N2—C16	1.4825 (19)	C14—C15	1.539 (2)
N3—C25	1.150 (2)	C14—H14	1.0000
O1—C17	1.2280 (18)	C15—C16	1.547 (2)
C2—C3	1.383 (2)	C15—H15A	0.9900
C2—H2	0.9500	C15—H15B	0.9900
C3—C10	1.443 (2)	C16—H16A	0.9900
C3—C4	1.446 (2)	C16—H16B	0.9900
C4—C5	1.396 (2)	C18—C19	1.510 (2)
C4—C9	1.409 (2)	C18—H18A	0.9900
C5—C6	1.380 (2)	C18—H18B	0.9900
C5—H5	0.9500	C19—C24	1.387 (2)
C6—C7	1.401 (2)	C19—C20	1.392 (2)
C6—H6	0.9500	C20—C21	1.384 (2)
C7—C8	1.379 (2)	C20—H20	0.9500
C7—H7	0.9500	C21—C22	1.395 (2)
C8—C9	1.391 (2)	C21—H21	0.9500
C8—H8	0.9500	C22—C23	1.392 (2)
C10—C11	1.342 (2)	C22—C25	1.442 (2)
C10—H10	0.9500	C23—C24	1.384 (2)
C11—C17	1.482 (2)	C23—H23	0.9500
C12—C13	1.549 (2)	C24—H24	0.9500
C12—H12A	0.9900
C2—N1—C9	108.68 (12)	H13A—C13—H13B	108.3
C2—N1—C18	127.10 (13)	C17—C14—C13	107.70 (13)
C9—N1—C18	124.18 (13)	C17—C14—C15	107.79 (13)
C11—N2—C12	108.02 (12)	C13—C14—C15	108.08 (13)
C11—N2—C16	108.35 (11)	C17—C14—H14	111.0
C12—N2—C16	108.05 (12)	C13—C14—H14	111.0
N1—C2—C3	110.60 (14)	C15—C14—H14	111.0
N1—C2—H2	124.7	C14—C15—C16	108.19 (12)
C3—C2—H2	124.7	C14—C15—H15A	110.1
C2—C3—C10	129.90 (14)	C16—C15—H15A	110.1
C2—C3—C4	105.74 (13)	C14—C15—H15B	110.1
C10—C3—C4	124.17 (13)	C16—C15—H15B	110.1
C5—C4—C9	119.08 (14)	H15A—C15—H15B	108.4
C5—C4—C3	133.84 (14)	N2—C16—C15	112.41 (12)
C9—C4—C3	107.03 (13)	N2—C16—H16A	109.1
C6—C5—C4	118.62 (15)	C15—C16—H16A	109.1
C6—C5—H5	120.7	N2—C16—H16B	109.1
C4—C5—H5	120.7	C15—C16—H16B	109.1
C5—C6—C7	121.38 (15)	H16A—C16—H16B	107.9
C5—C6—H6	119.3	O1—C17—C11	124.83 (15)
C7—C6—H6	119.3	O1—C17—C14	124.67 (14)
C8—C7—C6	121.27 (15)	C11—C17—C14	110.51 (13)
C8—C7—H7	119.4	N1—C18—C19	112.15 (12)
C6—C7—H7	119.4	N1—C18—H18A	109.2
C7—C8—C9	117.14 (15)	C19—C18—H18A	109.2
C7—C8—H8	121.4	N1—C18—H18B	109.2
C9—C8—H8	121.4	C19—C18—H18B	109.2
N1—C9—C8	129.54 (14)	H18A—C18—H18B	107.9
N1—C9—C4	107.93 (13)	C24—C19—C20	119.08 (14)
C8—C9—C4	122.50 (15)	C24—C19—C18	120.83 (14)
C11—C10—C3	129.13 (15)	C20—C19—C18	120.07 (13)
C11—C10—H10	115.4	C21—C20—C19	120.97 (14)
C3—C10—H10	115.4	C21—C20—H20	119.5
C10—C11—N2	123.45 (14)	C19—C20—H20	119.5
C10—C11—C17	122.77 (14)	C20—C21—C22	119.17 (15)
N2—C11—C17	113.76 (13)	C20—C21—H21	120.4
N2—C12—C13	111.92 (12)	C22—C21—H21	120.4
N2—C12—H12A	109.2	C23—C22—C21	120.39 (14)
C13—C12—H12A	109.2	C23—C22—C25	119.24 (14)
N2—C12—H12B	109.2	C21—C22—C25	120.35 (14)
C13—C12—H12B	109.2	C24—C23—C22	119.51 (14)
H12A—C12—H12B	107.9	C24—C23—H23	120.2
C14—C13—C12	108.64 (13)	C22—C23—H23	120.2
C14—C13—H13A	110.0	C23—C24—C19	120.82 (14)
C12—C13—H13A	110.0	C23—C24—H24	119.6
C14—C13—H13B	110.0	C19—C24—H24	119.6
C12—C13—H13B	110.0	N3—C25—C22	178.06 (17)
C9—N1—C2—C3	−0.32 (16)	C16—N2—C12—C13	59.45 (16)
C18—N1—C2—C3	−177.95 (13)	N2—C12—C13—C14	−0.11 (18)
N1—C2—C3—C10	174.58 (14)	C12—C13—C14—C17	56.92 (16)
N1—C2—C3—C4	−0.44 (16)	C12—C13—C14—C15	−59.29 (17)
C2—C3—C4—C5	178.37 (16)	C17—C14—C15—C16	−57.07 (16)
C10—C3—C4—C5	3.0 (3)	C13—C14—C15—C16	59.08 (16)
C2—C3—C4—C9	1.02 (16)	C11—N2—C16—C15	57.11 (16)
C10—C3—C4—C9	−174.37 (14)	C12—N2—C16—C15	−59.69 (16)
C9—C4—C5—C6	0.0 (2)	C14—C15—C16—N2	0.19 (18)
C3—C4—C5—C6	−177.08 (15)	C10—C11—C17—O1	−2.1 (2)
C4—C5—C6—C7	1.0 (2)	N2—C11—C17—O1	179.80 (13)
C5—C6—C7—C8	−1.0 (2)	C10—C11—C17—C14	177.55 (14)
C6—C7—C8—C9	0.0 (2)	N2—C11—C17—C14	−0.58 (17)
C2—N1—C9—C8	−176.79 (15)	C13—C14—C17—O1	121.88 (16)
C18—N1—C9—C8	0.9 (2)	C15—C14—C17—O1	−121.72 (16)
C2—N1—C9—C4	0.97 (16)	C13—C14—C17—C11	−57.74 (16)
C18—N1—C9—C4	178.69 (12)	C15—C14—C17—C11	58.66 (16)
C7—C8—C9—N1	178.54 (15)	C2—N1—C18—C19	−122.47 (16)
C7—C8—C9—C4	1.1 (2)	C9—N1—C18—C19	60.24 (18)
C5—C4—C9—N1	−179.04 (12)	N1—C18—C19—C24	42.68 (19)
C3—C4—C9—N1	−1.23 (16)	N1—C18—C19—C20	−135.82 (14)
C5—C4—C9—C8	−1.1 (2)	C24—C19—C20—C21	−2.6 (2)
C3—C4—C9—C8	176.73 (14)	C18—C19—C20—C21	175.96 (14)
C2—C3—C10—C11	−5.1 (3)	C19—C20—C21—C22	1.3 (2)
C4—C3—C10—C11	169.08 (15)	C20—C21—C22—C23	0.9 (2)
C3—C10—C11—N2	2.1 (2)	C20—C21—C22—C25	−177.41 (14)
C3—C10—C11—C17	−175.87 (14)	C21—C22—C23—C24	−1.7 (2)
C12—N2—C11—C10	−119.06 (15)	C25—C22—C23—C24	176.58 (14)
C16—N2—C11—C10	124.13 (15)	C22—C23—C24—C19	0.4 (2)
C12—N2—C11—C17	59.06 (15)	C20—C19—C24—C23	1.7 (2)
C16—N2—C11—C17	−57.76 (16)	C18—C19—C24—C23	−176.82 (14)
C11—N2—C12—C13	−57.57 (16)