(5-Ethenyl-1-aza-bicyclo-[2.2.2]octan-2-yl)(6-meth-oxy-3-quinol-yl)methanol methanol solvate.

In the title methanol solvate, C(20)H(24)N(2)O(2)·CH(4)O, an L-shaped conformation is found as the two substituents at the central hydr-oxy group are almost orthogonal to each other [the C-C-C angle at the central sp(3)-C atom is 110.12 (13)°]. The most notable feature of the crystal packing is the formation of supra-molecular chains along the b direction mediated by O-H⋯N hydrogen bonds occurring between the hydr-oxy and quinoline N atoms; the methanol mol-ecules are linked to these chains via O-H⋯N(amine) hydrogen bonds. C-H⋯O inter-actions also occur.

Related literature

For background to pre-catalyst mol­ecules for the Michael addition of acetone to trans-β-nitro­styrene, see: Mandal & Zhao (2008 ▶).

Experimental

Crystal data

C20H24N2O2·CH4O

M = 356.45

Orthorhombic,

a = 9.5374 (13) Å

b = 12.9842 (17) Å

c = 15.871 (2) Å

V = 1965.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 98 K

0.12 × 0.10 × 0.04 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.788, T max = 1.000

14410 measured reflections

2561 independent reflections

2501 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.08

2561 reflections

243 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); 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: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045073/hb5191sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045073/hb5191Isup2.hkl

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

C20H24N2O2·CH4O	F(000) = 768
Mr = 356.45	Dx = 1.205 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7299 reflections
a = 9.5374 (13) Å	θ = 2.0–40.2°
b = 12.9842 (17) Å	µ = 0.08 mm−1
c = 15.871 (2) Å	T = 98 K
V = 1965.4 (4) Å3	Platelet, colourless
Z = 4	0.12 × 0.10 × 0.04 mm

Rigaku AFC12K/SATURN724 diffractometer	2561 independent reflections
Radiation source: fine-focus sealed tube	2501 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.788, Tmax = 1.000	k = −16→16
14410 measured reflections	l = −18→20

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.067P)2 + 0.3164P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2561 reflections	Δρmax = 0.35 e Å−3
243 parameters	Δρmin = −0.27 e Å−3
2 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1	−0.09211 (13)	0.48893 (9)	0.86000 (8)	0.0208 (3)
H1O	−0.0859	0.5528	0.8526	0.031*
O2	0.56486 (13)	0.36533 (10)	0.77309 (8)	0.0235 (3)
O3	0.32503 (17)	0.60866 (12)	0.92437 (9)	0.0349 (4)
H3O	0.2607	0.5712	0.9435	0.052*
N1	0.12984 (17)	0.48168 (12)	1.00313 (9)	0.0245 (3)
N2	0.05966 (17)	0.19494 (12)	0.67553 (10)	0.0228 (3)
C1	0.08927 (18)	0.39987 (13)	0.94193 (10)	0.0191 (3)
H1	0.1754	0.3580	0.9312	0.023*
C2	−0.0200 (2)	0.32607 (14)	0.98034 (12)	0.0250 (4)
H2A	−0.1135	0.3393	0.9556	0.030*
H2B	0.0061	0.2537	0.9684	0.030*
C3	−0.0236 (2)	0.34482 (17)	1.07595 (13)	0.0299 (4)
H3	−0.0827	0.2913	1.1041	0.036*
C4	0.1270 (2)	0.33999 (17)	1.10976 (13)	0.0324 (5)
H4A	0.1711	0.2738	1.0936	0.039*
H4B	0.1266	0.3449	1.1720	0.039*
C5	0.2101 (2)	0.43074 (17)	1.07174 (13)	0.0304 (4)
H5A	0.2310	0.4816	1.1165	0.036*
H5B	0.3004	0.4051	1.0491	0.036*
C6	0.0053 (2)	0.53057 (16)	1.04185 (12)	0.0327 (5)
H6A	−0.0539	0.5607	0.9970	0.039*
H6B	0.0362	0.5872	1.0792	0.039*
C7	−0.0833 (2)	0.45269 (18)	1.09371 (12)	0.0329 (5)
H7	−0.0694	0.4681	1.1549	0.039*
C8	−0.2379 (3)	0.4605 (2)	1.07452 (16)	0.0498 (7)
H8	−0.2650	0.4626	1.0170	0.060*
C9	−0.3375 (3)	0.4646 (2)	1.13121 (18)	0.0534 (7)
H9A	−0.3145	0.4626	1.1894	0.064*
H9B	−0.4327	0.4695	1.1141	0.064*
C10	0.04468 (16)	0.44563 (13)	0.85620 (11)	0.0175 (3)
H10	0.1126	0.5010	0.8402	0.021*
C11	0.04985 (18)	0.36143 (13)	0.78993 (10)	0.0182 (3)
C12	−0.07008 (19)	0.31535 (14)	0.76062 (12)	0.0227 (4)
H12	−0.1593	0.3392	0.7787	0.027*
C13	−0.06039 (19)	0.23226 (15)	0.70350 (12)	0.0249 (4)
H13	−0.1449	0.2015	0.6842	0.030*
C14	0.18062 (18)	0.24173 (13)	0.70160 (10)	0.0196 (3)
C15	0.18147 (17)	0.32619 (13)	0.75884 (10)	0.0172 (3)
C16	0.31191 (18)	0.37064 (13)	0.78240 (10)	0.0180 (3)
H16	0.3137	0.4283	0.8193	0.022*
C17	0.43522 (18)	0.33065 (13)	0.75211 (11)	0.0191 (3)
C18	0.43402 (19)	0.24588 (14)	0.69502 (11)	0.0213 (3)
H18	0.5199	0.2187	0.6743	0.026*
C19	0.31040 (19)	0.20397 (14)	0.67016 (11)	0.0216 (3)
H19	0.3106	0.1485	0.6311	0.026*
C20	0.57014 (19)	0.44156 (15)	0.83814 (14)	0.0288 (4)
H20A	0.5219	0.5040	0.8191	0.043*
H20B	0.6682	0.4579	0.8510	0.043*
H20C	0.5240	0.4150	0.8888	0.043*
C21	0.3789 (4)	0.6699 (3)	0.98995 (18)	0.0793 (13)
H21A	0.3187	0.7303	0.9979	0.119*
H21B	0.4740	0.6925	0.9755	0.119*
H21C	0.3816	0.6296	1.0421	0.119*

	U11	U22	U33	U12	U13	U23
O1	0.0171 (6)	0.0161 (5)	0.0292 (6)	0.0017 (5)	0.0012 (5)	−0.0008 (5)
O2	0.0157 (5)	0.0233 (6)	0.0314 (6)	−0.0006 (5)	0.0013 (5)	−0.0028 (5)
O3	0.0421 (9)	0.0361 (8)	0.0265 (6)	−0.0121 (7)	0.0075 (6)	−0.0059 (6)
N1	0.0303 (8)	0.0229 (7)	0.0203 (6)	−0.0048 (6)	−0.0025 (6)	−0.0006 (6)
N2	0.0230 (7)	0.0193 (7)	0.0262 (7)	−0.0012 (6)	−0.0012 (6)	−0.0032 (6)
C1	0.0206 (8)	0.0166 (7)	0.0202 (7)	−0.0011 (6)	0.0009 (6)	0.0007 (6)
C2	0.0281 (9)	0.0209 (8)	0.0259 (8)	−0.0048 (7)	0.0028 (7)	0.0031 (7)
C3	0.0292 (9)	0.0362 (11)	0.0242 (8)	−0.0031 (8)	0.0029 (8)	0.0098 (8)
C4	0.0322 (10)	0.0360 (11)	0.0291 (9)	0.0001 (9)	−0.0013 (8)	0.0110 (8)
C5	0.0320 (10)	0.0346 (10)	0.0244 (8)	−0.0049 (8)	−0.0060 (8)	0.0027 (8)
C6	0.0487 (12)	0.0262 (10)	0.0234 (8)	0.0091 (9)	−0.0014 (9)	−0.0047 (8)
C7	0.0318 (10)	0.0468 (12)	0.0201 (8)	0.0083 (10)	0.0039 (8)	−0.0020 (8)
C8	0.0360 (12)	0.080 (2)	0.0335 (11)	0.0157 (13)	−0.0006 (10)	−0.0086 (13)
C9	0.0388 (12)	0.0715 (19)	0.0500 (14)	0.0109 (13)	0.0095 (11)	0.0000 (14)
C10	0.0151 (7)	0.0161 (7)	0.0212 (7)	0.0002 (6)	0.0008 (6)	−0.0003 (6)
C11	0.0189 (7)	0.0155 (7)	0.0201 (7)	−0.0002 (6)	0.0010 (6)	0.0012 (6)
C12	0.0178 (7)	0.0216 (8)	0.0288 (8)	0.0019 (7)	0.0005 (7)	−0.0039 (7)
C13	0.0208 (8)	0.0230 (8)	0.0311 (9)	−0.0020 (7)	−0.0030 (7)	−0.0047 (7)
C14	0.0218 (8)	0.0175 (8)	0.0195 (7)	0.0009 (7)	0.0005 (6)	−0.0014 (6)
C15	0.0181 (7)	0.0151 (7)	0.0184 (7)	0.0002 (6)	0.0003 (6)	0.0009 (6)
C16	0.0190 (7)	0.0163 (7)	0.0186 (7)	−0.0009 (6)	0.0003 (6)	0.0007 (6)
C17	0.0186 (7)	0.0180 (8)	0.0207 (7)	−0.0003 (6)	0.0004 (6)	0.0033 (6)
C18	0.0210 (7)	0.0211 (8)	0.0217 (8)	0.0039 (7)	0.0046 (7)	0.0008 (7)
C19	0.0252 (8)	0.0183 (8)	0.0212 (7)	0.0025 (7)	0.0019 (7)	−0.0023 (6)
C20	0.0171 (7)	0.0270 (9)	0.0422 (10)	−0.0017 (7)	−0.0009 (8)	−0.0092 (8)
C21	0.106 (3)	0.092 (3)	0.0397 (14)	−0.069 (2)	0.0241 (16)	−0.0203 (15)

O1—C10	1.4218 (19)	C7—C8	1.509 (3)
O1—H1O	0.8400	C7—H7	1.0000
O2—C17	1.357 (2)	C8—C9	1.309 (4)
O2—C20	1.431 (2)	C8—H8	0.9500
O3—C21	1.407 (3)	C9—H9A	0.9500
O3—H3O	0.8401	C9—H9B	0.9500
N1—C6	1.480 (3)	C10—C11	1.518 (2)
N1—C5	1.487 (2)	C10—H10	1.0000
N1—C1	1.490 (2)	C11—C12	1.372 (2)
N2—C13	1.320 (2)	C11—C15	1.424 (2)
N2—C14	1.368 (2)	C12—C13	1.412 (2)
C1—C2	1.541 (2)	C12—H12	0.9500
C1—C10	1.544 (2)	C13—H13	0.9500
C1—H1	1.0000	C14—C19	1.422 (2)
C2—C3	1.537 (3)	C14—C15	1.424 (2)
C2—H2A	0.9900	C15—C16	1.421 (2)
C2—H2B	0.9900	C16—C17	1.373 (2)
C3—C4	1.534 (3)	C16—H16	0.9500
C3—C7	1.538 (3)	C17—C18	1.426 (2)
C3—H3	1.0000	C18—C19	1.357 (3)
C4—C5	1.543 (3)	C18—H18	0.9500
C4—H4A	0.9900	C19—H19	0.9500
C4—H4B	0.9900	C20—H20A	0.9800
C5—H5A	0.9900	C20—H20B	0.9800
C5—H5B	0.9900	C20—H20C	0.9800
C6—C7	1.553 (3)	C21—H21A	0.9800
C6—H6A	0.9900	C21—H21B	0.9800
C6—H6B	0.9900	C21—H21C	0.9800
C10—O1—H1O	108.6	C9—C8—H8	117.5
C17—O2—C20	116.01 (13)	C7—C8—H8	117.5
C21—O3—H3O	109.2	C8—C9—H9A	120.0
C6—N1—C5	107.46 (15)	C8—C9—H9B	120.0
C6—N1—C1	111.58 (15)	H9A—C9—H9B	120.0
C5—N1—C1	107.09 (15)	O1—C10—C11	110.12 (13)
C13—N2—C14	117.82 (15)	O1—C10—C1	111.56 (13)
N1—C1—C2	111.16 (14)	C11—C10—C1	108.93 (14)
N1—C1—C10	111.80 (14)	O1—C10—H10	108.7
C2—C1—C10	113.66 (14)	C11—C10—H10	108.7
N1—C1—H1	106.6	C1—C10—H10	108.7
C2—C1—H1	106.6	C12—C11—C15	118.50 (15)
C10—C1—H1	106.6	C12—C11—C10	121.46 (15)
C3—C2—C1	107.88 (15)	C15—C11—C10	120.01 (14)
C3—C2—H2A	110.1	C11—C12—C13	119.75 (16)
C1—C2—H2A	110.1	C11—C12—H12	120.1
C3—C2—H2B	110.1	C13—C12—H12	120.1
C1—C2—H2B	110.1	N2—C13—C12	123.58 (17)
H2A—C2—H2B	108.4	N2—C13—H13	118.2
C4—C3—C2	108.53 (17)	C12—C13—H13	118.2
C4—C3—C7	108.63 (18)	N2—C14—C19	118.35 (15)
C2—C3—C7	109.48 (16)	N2—C14—C15	122.68 (15)
C4—C3—H3	110.1	C19—C14—C15	118.98 (15)
C2—C3—H3	110.1	C16—C15—C14	119.04 (15)
C7—C3—H3	110.1	C16—C15—C11	123.35 (15)
C3—C4—C5	108.25 (16)	C14—C15—C11	117.60 (15)
C3—C4—H4A	110.0	C17—C16—C15	120.28 (15)
C5—C4—H4A	110.0	C17—C16—H16	119.9
C3—C4—H4B	110.0	C15—C16—H16	119.9
C5—C4—H4B	110.0	O2—C17—C16	124.69 (16)
H4A—C4—H4B	108.4	O2—C17—C18	114.79 (15)
N1—C5—C4	111.18 (16)	C16—C17—C18	120.52 (16)
N1—C5—H5A	109.4	C19—C18—C17	120.08 (16)
C4—C5—H5A	109.4	C19—C18—H18	120.0
N1—C5—H5B	109.4	C17—C18—H18	120.0
C4—C5—H5B	109.4	C18—C19—C14	121.07 (16)
H5A—C5—H5B	108.0	C18—C19—H19	119.5
N1—C6—C7	112.16 (16)	C14—C19—H19	119.5
N1—C6—H6A	109.2	O2—C20—H20A	109.5
C7—C6—H6A	109.2	O2—C20—H20B	109.5
N1—C6—H6B	109.2	H20A—C20—H20B	109.5
C7—C6—H6B	109.2	O2—C20—H20C	109.5
H6A—C6—H6B	107.9	H20A—C20—H20C	109.5
C8—C7—C3	112.7 (2)	H20B—C20—H20C	109.5
C8—C7—C6	112.37 (19)	O3—C21—H21A	109.5
C3—C7—C6	107.13 (15)	O3—C21—H21B	109.5
C8—C7—H7	108.2	H21A—C21—H21B	109.5
C3—C7—H7	108.2	O3—C21—H21C	109.5
C6—C7—H7	108.2	H21A—C21—H21C	109.5
C9—C8—C7	124.9 (2)	H21B—C21—H21C	109.5
C6—N1—C1—C2	−48.65 (19)	C1—C10—C11—C12	103.71 (18)
C5—N1—C1—C2	68.68 (19)	O1—C10—C11—C15	163.18 (14)
C6—N1—C1—C10	79.54 (17)	C1—C10—C11—C15	−74.18 (19)
C5—N1—C1—C10	−163.12 (14)	C15—C11—C12—C13	2.5 (3)
N1—C1—C2—C3	−14.0 (2)	C10—C11—C12—C13	−175.43 (16)
C10—C1—C2—C3	−141.20 (16)	C14—N2—C13—C12	−2.0 (3)
C1—C2—C3—C4	−51.1 (2)	C11—C12—C13—N2	−0.1 (3)
C1—C2—C3—C7	67.3 (2)	C13—N2—C14—C19	−178.37 (17)
C2—C3—C4—C5	65.3 (2)	C13—N2—C14—C15	1.8 (3)
C7—C3—C4—C5	−53.6 (2)	N2—C14—C15—C16	−179.73 (16)
C6—N1—C5—C4	66.4 (2)	C19—C14—C15—C16	0.4 (2)
C1—N1—C5—C4	−53.6 (2)	N2—C14—C15—C11	0.6 (2)
C3—C4—C5—N1	−10.8 (2)	C19—C14—C15—C11	−179.29 (15)
C5—N1—C6—C7	−54.7 (2)	C12—C11—C15—C16	177.65 (17)
C1—N1—C6—C7	62.44 (19)	C10—C11—C15—C16	−4.4 (2)
C4—C3—C7—C8	−171.49 (17)	C12—C11—C15—C14	−2.7 (2)
C2—C3—C7—C8	70.1 (2)	C10—C11—C15—C14	175.28 (15)
C4—C3—C7—C6	64.42 (19)	C14—C15—C16—C17	−1.8 (2)
C2—C3—C7—C6	−53.9 (2)	C11—C15—C16—C17	177.88 (16)
N1—C6—C7—C8	−133.14 (19)	C20—O2—C17—C16	6.9 (2)
N1—C6—C7—C3	−8.8 (2)	C20—O2—C17—C18	−172.46 (15)
C3—C7—C8—C9	106.1 (3)	C15—C16—C17—O2	−177.66 (16)
C6—C7—C8—C9	−132.7 (3)	C15—C16—C17—C18	1.6 (2)
N1—C1—C10—O1	−76.08 (17)	O2—C17—C18—C19	179.34 (16)
C2—C1—C10—O1	50.77 (19)	C16—C17—C18—C19	0.0 (3)
N1—C1—C10—C11	162.15 (14)	C17—C18—C19—C14	−1.4 (3)
C2—C1—C10—C11	−71.00 (17)	N2—C14—C19—C18	−178.68 (17)
O1—C10—C11—C12	−18.9 (2)	C15—C14—C19—C18	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N1	0.84	1.95	2.783 (2)	171
O1—H1o···N2i	0.84	1.92	2.751 (2)	173
C20—H20b···O1ii	0.98	2.33	3.298 (2)	171
C18—H18···O3iii	0.95	2.58	3.471 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯N1	0.84	1.95	2.783 (2)	171
O1—H1o⋯N2i	0.84	1.92	2.751 (2)	173
C20—H20b⋯O1ii	0.98	2.33	3.298 (2)	171
C18—H18⋯O3iii	0.95	2.58	3.471 (2)	155

Symmetry codes: (i) ; (ii) ; (iii) .