2-(1-Benzyl-1H-indol-3-yl­methyl­ene)-1-aza­bi­cyclo­[2.2.2]­octan-3-one

The title compound, C₂₃H₂₂N₂O, was obtained in a condensation reaction of 1-benzyl-1H-indole-3-carbox­aldehyde with 1-aza-bi­cyclo­[2.2.2]­octan-3-one. The crystal structure indicates the presence of a double bond, connecting an aza­bicyclic ring system to an indole-3-carbox­aldehyde.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.057
• wR factor = 0.121
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C23 H22 N2 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in Siemens SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97 and local procedures.

2-(1-Benzyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2]octan-3-one

Crystal data

C23H22N2O	Z = 2
Mr = 342.43	F(000) = 364
Triclinic, P1	Dx = 1.280 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.245 (2) Å	Cell parameters from 26987 reflections
b = 10.015 (3) Å	θ = 1.0–27.5°
c = 11.245 (3) Å	µ = 0.08 mm^−1
α = 112.38 (2)°	T = 173 K
β = 92.78 (2)°	Irregular plate, pale yellow
γ = 109.51 (2)°	0.44 × 0.38 × 0.04 mm
V = 888.8 (4) Å^3

Data collection

Nonius KappaCCD diffractometer	2342 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
Detector resolution: 18 pixels mm^-1	h = −10→10
ω scans at fixed χ = 55°	k = −11→11
6198 measured reflections	l = −13→13
3118 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0457P)^2 + 0.2487P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3118 reflections	Δρmax = 0.15 e Å^−3
236 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (3)

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 (Ų)

	x	y	z	Uiso*/Ueq
O	0.34682 (17)	−0.55464 (17)	−0.11645 (14)	0.0435 (4)
N1	0.35684 (19)	0.02696 (19)	0.41524 (16)	0.0315 (4)
C2	0.3181 (2)	−0.1281 (2)	0.3371 (2)	0.0301 (5)
H2	0.2515	−0.2116	0.3540	0.036*
C3	0.3893 (2)	−0.1458 (2)	0.23060 (19)	0.0284 (5)
C4	0.4786 (2)	0.0103 (2)	0.2443 (2)	0.0302 (5)
C5	0.5734 (2)	0.0709 (3)	0.1686 (2)	0.0368 (5)
H5	0.5948	0.0037	0.0917	0.044*
C6	0.6348 (2)	0.2309 (3)	0.2090 (2)	0.0427 (6)
H6	0.6978	0.2734	0.1580	0.051*
C7	0.6067 (2)	0.3313 (3)	0.3225 (2)	0.0435 (6)
H7	0.6506	0.4406	0.3470	0.052*
C8	0.5169 (2)	0.2757 (2)	0.4000 (2)	0.0375 (6)
H8	0.4987	0.3443	0.4780	0.045*
C9	0.4535 (2)	0.1140 (2)	0.3590 (2)	0.0313 (5)
C10	0.3727 (2)	−0.2875 (2)	0.1199 (2)	0.0315 (5)
H10	0.4272	−0.2730	0.0535	0.038*
C11	0.2918 (2)	−0.4367 (2)	0.09660 (19)	0.0306 (5)
N12	0.21001 (19)	−0.48497 (19)	0.18864 (16)	0.0322 (4)
C13	0.2871 (3)	−0.5760 (2)	0.2253 (2)	0.0368 (5)
H13A	0.2361	−0.6084	0.2906	0.044*
H13B	0.3985	−0.5089	0.2666	0.044*
C14	0.2776 (3)	−0.7221 (3)	0.1047 (2)	0.0404 (6)
H14A	0.3841	−0.7213	0.0972	0.048*
H14B	0.2153	−0.8176	0.1147	0.048*
C15	0.2001 (2)	−0.7220 (2)	−0.0193 (2)	0.0369 (5)
H15	0.1985	−0.8114	−0.1003	0.044*
C16	0.0331 (3)	−0.7291 (3)	−0.0051 (2)	0.0431 (6)
H16A	−0.0303	−0.8288	−0.0019	0.052*
H16B	−0.0181	−0.7229	−0.0811	0.052*
C17	0.0454 (3)	−0.5898 (2)	0.1233 (2)	0.0402 (6)
H17A	−0.0099	−0.5293	0.1032	0.048*
H17B	−0.0073	−0.6301	0.1841	0.048*
C18	0.2886 (2)	−0.5678 (2)	−0.0233 (2)	0.0335 (5)
C19	0.2832 (3)	0.0897 (2)	0.5234 (2)	0.0353 (5)
H19A	0.3653	0.1766	0.5982	0.042*
H19B	0.2301	0.0072	0.5524	0.042*
C20	0.1650 (2)	0.1487 (2)	0.48625 (19)	0.0283 (5)
C21	0.1308 (2)	0.2620 (2)	0.5840 (2)	0.0331 (5)
H21	0.1815	0.3013	0.6728	0.040*
C22	0.0229 (3)	0.3182 (2)	0.5530 (2)	0.0385 (6)
H22	−0.0004	0.3954	0.6207	0.046*
C23	−0.0505 (2)	0.2628 (2)	0.4249 (2)	0.0392 (6)
H23	−0.1233	0.3025	0.4037	0.047*
C24	−0.0176 (2)	0.1489 (2)	0.3270 (2)	0.0364 (6)
H24	−0.0691	0.1092	0.2385	0.044*
C25	0.0896 (2)	0.0928 (2)	0.3574 (2)	0.0323 (5)
H25	0.1120	0.0151	0.2894	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O	0.0441 (9)	0.0507 (10)	0.0325 (9)	0.0171 (8)	0.0066 (8)	0.0153 (8)
N1	0.0323 (10)	0.0300 (10)	0.0351 (10)	0.0135 (8)	0.0061 (8)	0.0155 (8)
C2	0.0291 (11)	0.0291 (12)	0.0366 (13)	0.0123 (9)	0.0047 (10)	0.0176 (10)
C3	0.0232 (11)	0.0320 (12)	0.0328 (12)	0.0111 (9)	0.0033 (9)	0.0164 (10)
C4	0.0220 (11)	0.0358 (12)	0.0352 (13)	0.0095 (9)	−0.0002 (9)	0.0194 (11)
C5	0.0243 (11)	0.0475 (14)	0.0433 (14)	0.0113 (10)	0.0028 (10)	0.0266 (12)
C6	0.0243 (12)	0.0496 (15)	0.0591 (16)	0.0043 (11)	−0.0006 (11)	0.0374 (14)
C7	0.0285 (12)	0.0356 (13)	0.0635 (17)	0.0041 (10)	−0.0055 (12)	0.0267 (13)
C8	0.0305 (12)	0.0320 (12)	0.0467 (14)	0.0093 (10)	−0.0018 (10)	0.0167 (11)
C9	0.0251 (11)	0.0322 (12)	0.0379 (13)	0.0078 (9)	0.0009 (9)	0.0196 (11)
C10	0.0269 (11)	0.0393 (13)	0.0342 (12)	0.0155 (10)	0.0059 (9)	0.0191 (11)
C11	0.0286 (11)	0.0345 (12)	0.0301 (12)	0.0131 (10)	0.0050 (9)	0.0144 (10)
N12	0.0315 (10)	0.0306 (10)	0.0344 (10)	0.0112 (8)	0.0068 (8)	0.0142 (8)
C13	0.0369 (13)	0.0389 (13)	0.0338 (13)	0.0125 (10)	0.0030 (10)	0.0167 (11)
C14	0.0452 (14)	0.0389 (13)	0.0424 (14)	0.0204 (11)	0.0091 (11)	0.0187 (11)
C15	0.0399 (13)	0.0302 (12)	0.0344 (13)	0.0144 (10)	0.0028 (10)	0.0069 (10)
C16	0.0356 (13)	0.0361 (13)	0.0470 (15)	0.0083 (10)	−0.0023 (11)	0.0127 (11)
C17	0.0326 (12)	0.0390 (13)	0.0512 (15)	0.0138 (10)	0.0108 (11)	0.0209 (12)
C18	0.0286 (12)	0.0415 (13)	0.0318 (13)	0.0159 (10)	0.0007 (10)	0.0153 (11)
C19	0.0432 (13)	0.0343 (12)	0.0306 (12)	0.0159 (10)	0.0058 (10)	0.0153 (10)
C20	0.0300 (11)	0.0230 (11)	0.0304 (12)	0.0068 (9)	0.0050 (9)	0.0130 (10)
C21	0.0342 (12)	0.0280 (11)	0.0304 (12)	0.0053 (10)	0.0055 (10)	0.0113 (10)
C22	0.0374 (13)	0.0311 (12)	0.0447 (15)	0.0139 (10)	0.0134 (11)	0.0123 (11)
C23	0.0320 (12)	0.0373 (13)	0.0514 (15)	0.0134 (10)	0.0060 (11)	0.0220 (12)
C24	0.0329 (12)	0.0373 (13)	0.0359 (13)	0.0083 (10)	0.0014 (10)	0.0175 (11)
C25	0.0342 (12)	0.0295 (11)	0.0297 (12)	0.0097 (10)	0.0055 (10)	0.0111 (10)

Geometric parameters (Å, º)

O—C18	1.232 (2)	C13—H13B	0.9900
N1—C2	1.368 (3)	C14—C15	1.538 (3)
N1—C9	1.383 (3)	C14—H14A	0.9900
N1—C19	1.456 (3)	C14—H14B	0.9900
C2—C3	1.376 (3)	C15—C18	1.506 (3)
C2—H2	0.9500	C15—C16	1.541 (3)
C3—C10	1.442 (3)	C15—H15	1.0000
C3—C4	1.447 (3)	C16—C17	1.545 (3)
C4—C9	1.401 (3)	C16—H16A	0.9900
C4—C5	1.404 (3)	C16—H16B	0.9900
C5—C6	1.381 (3)	C17—H17A	0.9900
C5—H5	0.9500	C17—H17B	0.9900
C6—C7	1.392 (3)	C19—C20	1.514 (3)
C6—H6	0.9500	C19—H19A	0.9900
C7—C8	1.374 (3)	C19—H19B	0.9900
C7—H7	0.9500	C20—C21	1.385 (3)
C8—C9	1.396 (3)	C20—C25	1.387 (3)
C8—H8	0.9500	C21—C22	1.387 (3)
C10—C11	1.340 (3)	C21—H21	0.9500
C10—H10	0.9500	C22—C23	1.374 (3)
C11—N12	1.446 (2)	C22—H22	0.9500
C11—C18	1.471 (3)	C23—C24	1.383 (3)
N12—C17	1.481 (3)	C23—H23	0.9500
N12—C13	1.483 (3)	C24—C25	1.378 (3)
C13—C14	1.543 (3)	C24—H24	0.9500
C13—H13A	0.9900	C25—H25	0.9500
C2—N1—C9	108.68 (17)	H14A—C14—H14B	108.3
C2—N1—C19	125.50 (17)	C18—C15—C14	108.17 (17)
C9—N1—C19	124.65 (17)	C18—C15—C16	106.77 (17)
N1—C2—C3	110.27 (18)	C14—C15—C16	107.92 (18)
N1—C2—H2	124.9	C18—C15—H15	111.3
C3—C2—H2	124.9	C14—C15—H15	111.3
C2—C3—C10	128.90 (19)	C16—C15—H15	111.3
C2—C3—C4	106.13 (18)	C15—C16—C17	108.09 (18)
C10—C3—C4	124.81 (18)	C15—C16—H16A	110.1
C9—C4—C5	118.95 (19)	C17—C16—H16A	110.1
C9—C4—C3	106.86 (17)	C15—C16—H16B	110.1
C5—C4—C3	134.2 (2)	C17—C16—H16B	110.1
C6—C5—C4	118.2 (2)	H16A—C16—H16B	108.4
C6—C5—H5	120.9	N12—C17—C16	112.40 (17)
C4—C5—H5	120.9	N12—C17—H17A	109.1
C5—C6—C7	121.7 (2)	C16—C17—H17A	109.1
C5—C6—H6	119.2	N12—C17—H17B	109.1
C7—C6—H6	119.2	C16—C17—H17B	109.1
C8—C7—C6	121.5 (2)	H17A—C17—H17B	107.9
C8—C7—H7	119.3	O—C18—C11	125.0 (2)
C6—C7—H7	119.3	O—C18—C15	124.0 (2)
C7—C8—C9	117.1 (2)	C11—C18—C15	111.01 (18)
C7—C8—H8	121.5	N1—C19—C20	112.62 (16)
C9—C8—H8	121.5	N1—C19—H19A	109.1
N1—C9—C8	129.3 (2)	C20—C19—H19A	109.1
N1—C9—C4	108.05 (17)	N1—C19—H19B	109.1
C8—C9—C4	122.6 (2)	C20—C19—H19B	109.1
C11—C10—C3	129.6 (2)	H19A—C19—H19B	107.8
C11—C10—H10	115.2	C21—C20—C25	118.87 (19)
C3—C10—H10	115.2	C21—C20—C19	119.04 (18)
C10—C11—N12	124.16 (19)	C25—C20—C19	122.09 (18)
C10—C11—C18	122.05 (19)	C20—C21—C22	120.34 (19)
N12—C11—C18	113.64 (18)	C20—C21—H21	119.8
C11—N12—C17	109.50 (16)	C22—C21—H21	119.8
C11—N12—C13	107.01 (16)	C23—C22—C21	120.4 (2)
C17—N12—C13	107.97 (16)	C23—C22—H22	119.8
N12—C13—C14	111.59 (17)	C21—C22—H22	119.8
N12—C13—H13A	109.3	C22—C23—C24	119.5 (2)
C14—C13—H13A	109.3	C22—C23—H23	120.2
N12—C13—H13B	109.3	C24—C23—H23	120.2
C14—C13—H13B	109.3	C25—C24—C23	120.3 (2)
H13A—C13—H13B	108.0	C25—C24—H24	119.9
C15—C14—C13	109.00 (17)	C23—C24—H24	119.9
C15—C14—H14A	109.9	C24—C25—C20	120.60 (19)
C13—C14—H14A	109.9	C24—C25—H25	119.7
C15—C14—H14B	109.9	C20—C25—H25	119.7
C13—C14—H14B	109.9
C9—N1—C2—C3	0.9 (2)	C11—N12—C13—C14	−60.7 (2)
C19—N1—C2—C3	168.89 (17)	C17—N12—C13—C14	57.1 (2)
N1—C2—C3—C10	−175.44 (18)	N12—C13—C14—C15	4.0 (2)
N1—C2—C3—C4	0.0 (2)	C13—C14—C15—C18	53.7 (2)
C2—C3—C4—C9	−0.9 (2)	C13—C14—C15—C16	−61.5 (2)
C10—C3—C4—C9	174.82 (18)	C18—C15—C16—C17	−59.7 (2)
C2—C3—C4—C5	−178.8 (2)	C14—C15—C16—C17	56.4 (2)
C10—C3—C4—C5	−3.2 (3)	C11—N12—C17—C16	53.7 (2)
C9—C4—C5—C6	−1.6 (3)	C13—N12—C17—C16	−62.4 (2)
C3—C4—C5—C6	176.1 (2)	C15—C16—C17—N12	4.5 (2)
C4—C5—C6—C7	1.0 (3)	C10—C11—C18—O	−6.2 (3)
C5—C6—C7—C8	0.2 (3)	N12—C11—C18—O	178.02 (18)
C6—C7—C8—C9	−0.7 (3)	C10—C11—C18—C15	175.39 (18)
C2—N1—C9—C8	177.0 (2)	N12—C11—C18—C15	−0.4 (2)
C19—N1—C9—C8	8.9 (3)	C14—C15—C18—O	124.6 (2)
C2—N1—C9—C4	−1.4 (2)	C16—C15—C18—O	−119.5 (2)
C19—N1—C9—C4	−169.55 (17)	C14—C15—C18—C11	−57.0 (2)
C7—C8—C9—N1	−178.21 (18)	C16—C15—C18—C11	58.9 (2)
C7—C8—C9—C4	0.0 (3)	C2—N1—C19—C20	−101.0 (2)
C5—C4—C9—N1	179.74 (16)	C9—N1—C19—C20	65.2 (2)
C3—C4—C9—N1	1.4 (2)	N1—C19—C20—C21	−155.31 (17)
C5—C4—C9—C8	1.2 (3)	N1—C19—C20—C25	24.8 (3)
C3—C4—C9—C8	−177.16 (18)	C25—C20—C21—C22	−0.1 (3)
C2—C3—C10—C11	−4.4 (3)	C19—C20—C21—C22	−179.94 (18)
C4—C3—C10—C11	−179.0 (2)	C20—C21—C22—C23	−0.4 (3)
C3—C10—C11—N12	−4.6 (3)	C21—C22—C23—C24	0.8 (3)
C3—C10—C11—C18	−179.90 (18)	C22—C23—C24—C25	−0.9 (3)
C10—C11—N12—C17	127.2 (2)	C23—C24—C25—C20	0.4 (3)
C18—C11—N12—C17	−57.1 (2)	C21—C20—C25—C24	0.0 (3)
C10—C11—N12—C13	−116.0 (2)	C19—C20—C25—C24	179.90 (19)
C18—C11—N12—C13	59.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N12	0.95	2.54	3.077 (3)	116
C10—H10···O	0.95	2.55	2.894 (3)	101
C21—H21···O^i	0.95	2.37	3.301 (3)	167

Symmetry code: (i) x, y+1, z+1.