(Z)-2-(2,4-Di­methoxy­benzyl­idene)-1-aza­bi­cyclo­[2.2.2]­octan-3-ol

The title compound, C₁₆H₂₁NO₃, crystallizes in the monoclinic space group P2₁/c. The 2,4-di­methoxy­phenyl ring is twisted by -39.8 (2)° with respect to the plane of the double bond connected to the aza­bicyclic ring system. In addition to intermolecular hydrogen bonding, mol­ecules are held together in the solid state by van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.130
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

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Alert level C
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   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
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   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 and local procedures.

(Z)-2-(2,4-Dimethoxybenzylidene)-1-aza-bicyclo[2.2.2]octan-3-ol

Crystal data

C16H21NO3	F(000) = 592
Mr = 275.34	Dx = 1.353 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.2061 (1) Å	Cell parameters from 3205 reflections
b = 14.0232 (3) Å	θ = 1.0–27.5°
c = 15.8208 (4) Å	µ = 0.09 mm^−1
β = 101.0515 (10)°	T = 90 K
V = 1351.34 (5) Å^3	Semi-regular block, colourless
Z = 4	0.25 × 0.18 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer	2241 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 27.4°, θmin = 2.0°
Detector resolution: 18 pixels mm^-1	h = −8→8
ω scans at fixed χ = 55°	k = −17→18
5998 measured reflections	l = −20→20
3074 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.49	w = 1/[σ^2(Fo^2) + (0.0764P)^2 + 0.0831P] where P = (Fo^2 + 2Fc^2)/3
3074 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−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
O1	0.63491 (18)	−0.02856 (8)	0.60524 (7)	0.0237 (3)
C1	0.4384 (2)	0.11000 (11)	0.77345 (9)	0.0176 (3)
H1	0.4635	0.1692	0.8029	0.021*
O2	0.08977 (17)	−0.09628 (7)	0.77046 (6)	0.0202 (3)
C2	0.5641 (2)	0.08700 (11)	0.71187 (9)	0.0187 (3)
H2	0.6740	0.1296	0.7004	0.022*
O3	−0.18318 (17)	0.18090 (8)	0.92668 (6)	0.0204 (3)
H3	−0.3000	0.1615	0.9403	0.031*
C3	0.5265 (2)	0.00169 (11)	0.66799 (9)	0.0182 (4)
C4	0.3666 (2)	−0.06179 (11)	0.68585 (9)	0.0180 (3)
H4	0.3412	−0.1205	0.6557	0.022*
C5	0.2462 (2)	−0.03807 (10)	0.74790 (9)	0.0160 (3)
C6	0.2782 (2)	0.04946 (11)	0.79320 (9)	0.0163 (3)
C7	0.7915 (3)	0.03504 (12)	0.58064 (11)	0.0247 (4)
H7A	0.7187	0.0949	0.5597	0.037*
H7B	0.8553	0.0058	0.5348	0.037*
H7C	0.9080	0.0481	0.6305	0.037*
C8	0.0472 (3)	−0.18439 (11)	0.72497 (10)	0.0240 (4)
H8A	0.0000	−0.1715	0.6633	0.036*
H8B	−0.0688	−0.2191	0.7462	0.036*
H8C	0.1813	−0.2230	0.7342	0.036*
C9	0.1347 (2)	0.07283 (10)	0.85423 (9)	0.0162 (3)
H9	−0.0134	0.0527	0.8370	0.019*
C10	0.1788 (2)	0.11776 (10)	0.92986 (9)	0.0151 (3)
N11	0.3950 (2)	0.15197 (9)	0.97025 (7)	0.0159 (3)
C12	0.4468 (2)	0.11290 (11)	1.05954 (9)	0.0195 (4)
H12A	0.5978	0.1318	1.0869	0.023*
H12B	0.4412	0.0424	1.0570	0.023*
C13	0.2845 (3)	0.14911 (11)	1.11512 (9)	0.0197 (4)
H13A	0.2238	0.0946	1.1427	0.024*
H13B	0.3612	0.1919	1.1610	0.024*
C14	0.0991 (2)	0.20316 (11)	1.05691 (9)	0.0172 (3)
H14	−0.0158	0.2224	1.0901	0.021*
C15	−0.0001 (2)	0.13813 (11)	0.98171 (9)	0.0162 (3)
H15	−0.0474	0.0768	1.0048	0.019*
C16	0.1958 (2)	0.29139 (11)	1.02062 (9)	0.0192 (4)
H16A	0.2528	0.3366	1.0677	0.023*
H16B	0.0812	0.3241	0.9785	0.023*
C17	0.3837 (2)	0.25772 (11)	0.97644 (9)	0.0190 (3)
H17A	0.3623	0.2853	0.9178	0.023*
H17B	0.5251	0.2818	1.0094	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0274 (7)	0.0222 (6)	0.0252 (6)	−0.0003 (5)	0.0147 (5)	−0.0020 (5)
C1	0.0182 (8)	0.0181 (8)	0.0157 (7)	0.0015 (6)	0.0013 (6)	−0.0009 (6)
O2	0.0224 (6)	0.0185 (6)	0.0217 (6)	−0.0052 (5)	0.0091 (5)	−0.0051 (4)
C2	0.0177 (8)	0.0201 (8)	0.0184 (7)	−0.0023 (7)	0.0041 (6)	0.0012 (6)
O3	0.0129 (5)	0.0273 (6)	0.0209 (5)	0.0013 (5)	0.0032 (4)	0.0026 (5)
C3	0.0197 (8)	0.0205 (8)	0.0154 (7)	0.0049 (7)	0.0061 (6)	0.0021 (6)
C4	0.0220 (8)	0.0159 (8)	0.0162 (7)	0.0016 (7)	0.0041 (6)	−0.0018 (6)
C5	0.0156 (8)	0.0176 (8)	0.0146 (7)	0.0006 (6)	0.0024 (6)	0.0012 (6)
C6	0.0146 (8)	0.0186 (8)	0.0149 (7)	0.0020 (6)	0.0011 (6)	−0.0003 (6)
C7	0.0248 (9)	0.0241 (9)	0.0290 (9)	0.0022 (7)	0.0147 (7)	0.0047 (7)
C8	0.0307 (9)	0.0203 (9)	0.0224 (8)	−0.0066 (7)	0.0083 (7)	−0.0051 (7)
C9	0.0143 (8)	0.0159 (8)	0.0184 (7)	−0.0011 (6)	0.0036 (6)	0.0001 (6)
C10	0.0151 (8)	0.0131 (7)	0.0173 (7)	0.0002 (6)	0.0033 (6)	0.0012 (6)
N11	0.0150 (7)	0.0167 (7)	0.0156 (6)	−0.0002 (5)	0.0020 (5)	−0.0001 (5)
C12	0.0179 (8)	0.0238 (8)	0.0164 (7)	0.0029 (7)	0.0025 (6)	0.0012 (6)
C13	0.0205 (8)	0.0235 (8)	0.0153 (7)	0.0003 (7)	0.0035 (6)	0.0000 (6)
C14	0.0161 (8)	0.0190 (8)	0.0171 (7)	0.0019 (7)	0.0052 (6)	−0.0019 (6)
C15	0.0136 (8)	0.0188 (8)	0.0167 (7)	0.0014 (6)	0.0039 (6)	−0.0001 (6)
C16	0.0184 (8)	0.0180 (8)	0.0213 (8)	0.0005 (7)	0.0037 (6)	−0.0029 (6)
C17	0.0181 (8)	0.0158 (8)	0.0238 (8)	−0.0029 (6)	0.0055 (6)	−0.0030 (6)

Geometric parameters (Å, º)

O1—C3	1.3691 (17)	C9—C10	1.333 (2)
O1—C7	1.4270 (18)	C9—H9	0.9500
C1—C6	1.387 (2)	C10—N11	1.4523 (19)
C1—C2	1.398 (2)	C10—C15	1.529 (2)
C1—H1	0.9500	N11—C17	1.4888 (19)
O2—C5	1.3673 (17)	N11—C12	1.4916 (18)
O2—C8	1.4287 (18)	C12—C13	1.544 (2)
C2—C3	1.380 (2)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
O3—C15	1.4245 (17)	C13—C14	1.530 (2)
O3—H3	0.8400	C13—H13A	0.9900
C3—C4	1.401 (2)	C13—H13B	0.9900
C4—C5	1.383 (2)	C14—C15	1.531 (2)
C4—H4	0.9500	C14—C16	1.534 (2)
C5—C6	1.416 (2)	C14—H14	1.0000
C6—C9	1.471 (2)	C15—H15	1.0000
C7—H7A	0.9800	C16—C17	1.544 (2)
C7—H7B	0.9800	C16—H16A	0.9900
C7—H7C	0.9800	C16—H16B	0.9900
C8—H8A	0.9800	C17—H17A	0.9900
C8—H8B	0.9800	C17—H17B	0.9900
C8—H8C	0.9800
C3—O1—C7	117.34 (12)	C10—N11—C17	107.88 (12)
C6—C1—C2	122.38 (14)	C10—N11—C12	107.98 (11)
C6—C1—H1	118.8	C17—N11—C12	107.93 (11)
C2—C1—H1	118.8	N11—C12—C13	111.88 (12)
C5—O2—C8	117.17 (11)	N11—C12—H12A	109.2
C3—C2—C1	119.17 (14)	C13—C12—H12A	109.2
C3—C2—H2	120.4	N11—C12—H12B	109.2
C1—C2—H2	120.4	C13—C12—H12B	109.2
C15—O3—H3	109.5	H12A—C12—H12B	107.9
O1—C3—C2	125.03 (13)	C14—C13—C12	108.52 (12)
O1—C3—C4	114.51 (13)	C14—C13—H13A	110.0
C2—C3—C4	120.46 (13)	C12—C13—H13A	110.0
C5—C4—C3	119.34 (14)	C14—C13—H13B	110.0
C5—C4—H4	120.3	C12—C13—H13B	110.0
C3—C4—H4	120.3	H13A—C13—H13B	108.4
O2—C5—C4	123.29 (13)	C13—C14—C15	108.46 (12)
O2—C5—C6	115.03 (12)	C13—C14—C16	108.76 (12)
C4—C5—C6	121.68 (13)	C15—C14—C16	108.51 (12)
C1—C6—C5	116.96 (13)	C13—C14—H14	110.4
C1—C6—C9	124.17 (14)	C15—C14—H14	110.4
C5—C6—C9	118.79 (13)	C16—C14—H14	110.4
O1—C7—H7A	109.5	O3—C15—C10	109.09 (11)
O1—C7—H7B	109.5	O3—C15—C14	112.26 (12)
H7A—C7—H7B	109.5	C10—C15—C14	107.63 (12)
O1—C7—H7C	109.5	O3—C15—H15	109.3
H7A—C7—H7C	109.5	C10—C15—H15	109.3
H7B—C7—H7C	109.5	C14—C15—H15	109.3
O2—C8—H8A	109.5	C14—C16—C17	107.86 (12)
O2—C8—H8B	109.5	C14—C16—H16A	110.1
H8A—C8—H8B	109.5	C17—C16—H16A	110.1
O2—C8—H8C	109.5	C14—C16—H16B	110.1
H8A—C8—H8C	109.5	C17—C16—H16B	110.1
H8B—C8—H8C	109.5	H16A—C16—H16B	108.4
C10—C9—C6	130.41 (14)	N11—C17—C16	112.54 (12)
C10—C9—H9	114.8	N11—C17—H17A	109.1
C6—C9—H9	114.8	C16—C17—H17A	109.1
C9—C10—N11	124.37 (13)	N11—C17—H17B	109.1
C9—C10—C15	121.62 (13)	C16—C17—H17B	109.1
N11—C10—C15	114.01 (12)	H17A—C17—H17B	107.8
C6—C1—C2—C3	0.9 (2)	C15—C10—N11—C17	−63.02 (15)
C7—O1—C3—C2	−3.1 (2)	C9—C10—N11—C12	−126.95 (15)
C7—O1—C3—C4	176.69 (13)	C15—C10—N11—C12	53.39 (15)
C1—C2—C3—O1	178.77 (13)	C10—N11—C12—C13	−62.76 (15)
C1—C2—C3—C4	−1.0 (2)	C17—N11—C12—C13	53.62 (16)
O1—C3—C4—C5	−179.65 (13)	N11—C12—C13—C14	8.10 (18)
C2—C3—C4—C5	0.1 (2)	C12—C13—C14—C15	53.92 (16)
C8—O2—C5—C4	−1.8 (2)	C12—C13—C14—C16	−63.91 (15)
C8—O2—C5—C6	178.39 (13)	C9—C10—C15—O3	−49.41 (19)
C3—C4—C5—O2	−178.89 (14)	N11—C10—C15—O3	130.26 (12)
C3—C4—C5—C6	0.9 (2)	C9—C10—C15—C14	−171.46 (13)
C2—C1—C6—C5	0.0 (2)	N11—C10—C15—C14	8.21 (16)
C2—C1—C6—C9	−176.76 (14)	C13—C14—C15—O3	176.60 (11)
O2—C5—C6—C1	178.85 (12)	C16—C14—C15—O3	−65.42 (15)
C4—C5—C6—C1	−0.9 (2)	C13—C14—C15—C10	−63.35 (15)
O2—C5—C6—C9	−4.2 (2)	C16—C14—C15—C10	54.64 (15)
C4—C5—C6—C9	176.04 (13)	C13—C14—C16—C17	54.46 (15)
C1—C6—C9—C10	−39.8 (2)	C15—C14—C16—C17	−63.34 (15)
C5—C6—C9—C10	143.48 (16)	C10—N11—C17—C16	52.79 (15)
C6—C9—C10—N11	−2.1 (3)	C12—N11—C17—C16	−63.65 (15)
C6—C9—C10—C15	177.50 (14)	C14—C16—C17—N11	8.38 (17)
C9—C10—N11—C17	116.64 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N11^i	0.84	2.04	2.8610 (16)	165

Symmetry code: (i) x−1, y, z.