2-((E)-{(S)-(6-Meth-oxy-quinolin-4-yl)[(2S)-8-vinyl-quinuclidin-2-yl]methyl-imino}-meth-yl)phenol.

The title compound, C(27)H(29)N(3)O(2), adopts an E configuration with respect to the C=N bond. The molecular structure is stabilized by inter-molecular O-H⋯N inter-actions between a hy-droxy H atom and the N atom on the quinoline ring.

Related literature

For literature on the preparation of Schiff base compounds, see: Jennings & Lovely (1991 ▶); Yoon & Jacobsen (2005 ▶). For the uses of Schiff base compounds, see: Yin et al. (2004 ▶). For the crystal structures of Schiff base compounds, see: Zhu (2011 ▶); Xie et al. (2010 ▶). For reference bond values, see: Jones (1986 ▶); Hooft et al. (2008 ▶). For information on the absolute structure of the title compound, see: Brunner et al. (1995 ▶); He et al. (2006 ▶).

Experimental

Crystal data

C27H29N3O2

M = 427.53

Orthorhombic,

a = 8.9285 (15) Å

b = 11.6759 (19) Å

c = 21.939 (4) Å

V = 2287.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.35 × 0.29 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.973, T max = 0.987

11474 measured reflections

2339 independent reflections

2098 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.05

2339 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.10 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021507/jh2284sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021507/jh2284Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021507/jh2284Isup3.cml

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

C27H29N3O2	Dx = 1.242 Mg m−3
Mr = 427.53	Melting point: 438(1) K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 8.9285 (15) Å	Cell parameters from 4474 reflections
b = 11.6759 (19) Å	θ = 2.5–27.8°
c = 21.939 (4) Å	µ = 0.08 mm−1
V = 2287.1 (7) Å3	T = 296 K
Z = 4	Block, yellow
F(000) = 912	0.35 × 0.29 × 0.17 mm

Bruker APEXII CCD diffractometer	2339 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→10
Tmin = 0.973, Tmax = 0.987	k = −13→12
11474 measured reflections	l = −26→23

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.044P)2 + 0.2035P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2339 reflections	Δρmax = 0.10 e Å−3
292 parameters	Δρmin = −0.10 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (11)

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.

	x	y	z	Uiso*/Ueq
N1	0.41218 (19)	0.89212 (15)	0.85006 (7)	0.0446 (4)
N2	0.2454 (2)	1.09111 (16)	0.66032 (9)	0.0596 (5)
N3	0.7031 (2)	0.98276 (17)	0.88131 (7)	0.0534 (5)
O1	0.2162 (2)	0.92618 (13)	0.93612 (7)	0.0639 (4)
H1	0.2749	0.9431	0.9088	0.096*
O2	0.6132 (2)	0.73226 (15)	0.59318 (7)	0.0676 (5)
C1	0.2036 (2)	0.81020 (19)	0.93959 (8)	0.0478 (5)
C2	0.1042 (3)	0.7639 (2)	0.98102 (10)	0.0648 (7)
H2	0.0469	0.8116	1.0057	0.078*
C3	0.0903 (3)	0.6468 (2)	0.98559 (11)	0.0714 (7)
H3	0.0236	0.6159	1.0137	0.086*
C4	0.1735 (3)	0.5744 (2)	0.94915 (11)	0.0706 (7)
H4	0.1627	0.4954	0.9524	0.085*
C5	0.2728 (3)	0.62049 (19)	0.90787 (11)	0.0578 (6)
H5	0.3295	0.5720	0.8834	0.069*
C6	0.2897 (2)	0.73866 (18)	0.90213 (8)	0.0443 (5)
C7	0.3947 (2)	0.78523 (18)	0.85793 (9)	0.0446 (5)
H7	0.4513	0.7348	0.8345	0.054*
C8	0.5154 (2)	0.93012 (18)	0.80204 (8)	0.0425 (5)
H8	0.5719	0.8644	0.7865	0.051*
C9	0.4216 (2)	0.98194 (16)	0.75096 (8)	0.0413 (4)
C10	0.3234 (2)	1.06841 (19)	0.76429 (10)	0.0518 (5)
H10	0.3131	1.0932	0.8043	0.062*
C11	0.2389 (3)	1.1196 (2)	0.71834 (12)	0.0573 (6)
H11	0.1733	1.1779	0.7294	0.069*
C12	0.3404 (2)	1.00365 (19)	0.64556 (10)	0.0494 (5)
C13	0.3487 (3)	0.9714 (2)	0.58382 (10)	0.0596 (6)
H13	0.2916	1.0107	0.5552	0.071*
C14	0.4382 (3)	0.8840 (2)	0.56510 (9)	0.0601 (6)
H14	0.4423	0.8643	0.5241	0.072*
C15	0.5242 (2)	0.82375 (19)	0.60786 (9)	0.0495 (5)
C16	0.5222 (2)	0.85392 (18)	0.66807 (9)	0.0458 (5)
H16	0.5816	0.8140	0.6957	0.055*
C17	0.4310 (2)	0.94490 (17)	0.68904 (8)	0.0410 (4)
C18	0.6243 (2)	1.02128 (19)	0.82638 (8)	0.0465 (5)
H18	0.5647	1.0885	0.8377	0.056*
C19	0.7364 (3)	1.0596 (2)	0.77607 (10)	0.0639 (7)
H19A	0.7236	1.0129	0.7399	0.077*
H19B	0.7184	1.1390	0.7652	0.077*
C20	0.8952 (3)	1.0458 (2)	0.80107 (11)	0.0639 (6)
H20	0.9683	1.0689	0.7701	0.077*
C21	0.9177 (3)	0.9201 (2)	0.81741 (14)	0.0804 (8)
H21A	1.0195	0.9076	0.8313	0.096*
H21B	0.9003	0.8724	0.7819	0.096*
C22	0.8070 (3)	0.8886 (2)	0.86801 (12)	0.0674 (7)
H22A	0.7502	0.8216	0.8558	0.081*
H22B	0.8621	0.8693	0.9047	0.081*
C23	0.7916 (3)	1.0797 (2)	0.90419 (10)	0.0636 (6)
H23A	0.8376	1.0582	0.9426	0.076*
H23B	0.7251	1.1438	0.9119	0.076*
C24	0.9161 (3)	1.1181 (2)	0.85889 (11)	0.0603 (6)
H24	1.0135	1.0987	0.8768	0.072*
C25	0.9125 (3)	1.2447 (2)	0.84784 (13)	0.0727 (7)
H25	0.8233	1.2750	0.8330	0.087*
C26	1.0210 (4)	1.3160 (3)	0.85690 (14)	0.0932 (9)
H26A	1.1125	1.2899	0.8717	0.112*
H26B	1.0077	1.3935	0.8486	0.112*
C27	0.6104 (4)	0.6886 (3)	0.53269 (10)	0.0893 (9)
H27A	0.6449	0.7465	0.5050	0.134*
H27B	0.5099	0.6670	0.5222	0.134*
H27C	0.6746	0.6228	0.5300	0.134*

	U11	U22	U33	U12	U13	U23
N1	0.0486 (9)	0.0457 (10)	0.0395 (9)	−0.0028 (8)	0.0046 (7)	0.0016 (7)
N2	0.0560 (11)	0.0516 (11)	0.0712 (13)	0.0021 (10)	−0.0051 (10)	0.0136 (10)
N3	0.0598 (11)	0.0577 (11)	0.0426 (9)	−0.0051 (10)	−0.0053 (8)	−0.0014 (8)
O1	0.0809 (11)	0.0513 (9)	0.0596 (9)	0.0002 (9)	0.0226 (9)	−0.0035 (8)
O2	0.0864 (11)	0.0694 (11)	0.0469 (8)	0.0073 (10)	0.0076 (8)	−0.0099 (8)
C1	0.0538 (12)	0.0507 (13)	0.0390 (10)	−0.0019 (10)	0.0019 (10)	0.0014 (9)
C2	0.0707 (15)	0.0719 (17)	0.0517 (13)	−0.0034 (14)	0.0177 (12)	0.0014 (12)
C3	0.0781 (17)	0.0786 (18)	0.0574 (14)	−0.0175 (15)	0.0167 (13)	0.0138 (13)
C4	0.0897 (18)	0.0547 (15)	0.0674 (15)	−0.0137 (15)	0.0075 (14)	0.0125 (13)
C5	0.0679 (14)	0.0463 (13)	0.0591 (13)	−0.0017 (12)	0.0074 (12)	0.0038 (11)
C6	0.0482 (11)	0.0473 (12)	0.0375 (9)	−0.0018 (9)	−0.0014 (9)	0.0036 (9)
C7	0.0479 (11)	0.0454 (12)	0.0405 (10)	0.0012 (10)	0.0033 (9)	−0.0003 (9)
C8	0.0442 (10)	0.0453 (11)	0.0379 (9)	−0.0011 (9)	0.0046 (8)	0.0007 (9)
C9	0.0408 (10)	0.0394 (10)	0.0438 (10)	−0.0071 (9)	0.0025 (8)	0.0045 (9)
C10	0.0516 (12)	0.0479 (12)	0.0559 (12)	0.0017 (11)	0.0078 (10)	0.0002 (10)
C11	0.0530 (12)	0.0456 (12)	0.0734 (16)	0.0042 (11)	0.0064 (11)	0.0093 (11)
C12	0.0488 (11)	0.0470 (12)	0.0523 (12)	−0.0088 (10)	−0.0035 (10)	0.0095 (10)
C13	0.0674 (14)	0.0602 (14)	0.0510 (12)	−0.0078 (13)	−0.0152 (11)	0.0141 (11)
C14	0.0752 (15)	0.0676 (16)	0.0375 (11)	−0.0139 (14)	−0.0051 (11)	0.0019 (11)
C15	0.0566 (12)	0.0479 (12)	0.0441 (11)	−0.0086 (11)	0.0055 (10)	−0.0015 (9)
C16	0.0497 (11)	0.0465 (12)	0.0413 (10)	−0.0045 (10)	−0.0020 (9)	0.0030 (9)
C17	0.0401 (10)	0.0406 (11)	0.0422 (9)	−0.0085 (8)	−0.0010 (8)	0.0040 (9)
C18	0.0502 (11)	0.0476 (12)	0.0415 (10)	−0.0052 (10)	0.0022 (9)	−0.0005 (9)
C19	0.0603 (13)	0.0809 (17)	0.0504 (12)	−0.0277 (14)	0.0008 (11)	0.0005 (13)
C20	0.0519 (12)	0.0726 (17)	0.0672 (14)	−0.0130 (12)	0.0106 (11)	−0.0142 (13)
C21	0.0683 (15)	0.0689 (18)	0.104 (2)	−0.0005 (14)	0.0052 (16)	−0.0314 (16)
C22	0.0717 (15)	0.0593 (15)	0.0713 (15)	0.0022 (13)	−0.0193 (13)	−0.0007 (12)
C23	0.0668 (14)	0.0665 (15)	0.0574 (13)	−0.0067 (13)	−0.0074 (12)	−0.0147 (12)
C24	0.0481 (12)	0.0574 (14)	0.0755 (15)	−0.0019 (11)	−0.0123 (11)	−0.0088 (12)
C25	0.0646 (15)	0.0635 (16)	0.0900 (19)	0.0015 (14)	−0.0104 (14)	−0.0072 (14)
C26	0.091 (2)	0.0693 (19)	0.119 (2)	−0.0187 (18)	−0.003 (2)	−0.0112 (18)
C27	0.133 (3)	0.084 (2)	0.0506 (13)	0.006 (2)	0.0223 (16)	−0.0132 (14)

N1—C7	1.269 (3)	C13—C14	1.359 (3)
N1—C8	1.468 (2)	C13—H13	0.9300
N2—C11	1.317 (3)	C14—C15	1.402 (3)
N2—C12	1.367 (3)	C14—H14	0.9300
N3—C18	1.466 (3)	C15—C16	1.367 (3)
N3—C22	1.468 (3)	C16—C17	1.415 (3)
N3—C23	1.468 (3)	C16—H16	0.9300
O1—C1	1.361 (3)	C18—C19	1.556 (3)
O1—H1	0.8200	C18—H18	0.9800
O2—C15	1.369 (3)	C19—C20	1.529 (3)
O2—C27	1.422 (3)	C19—H19A	0.9700
C1—C2	1.380 (3)	C19—H19B	0.9700
C1—C6	1.401 (3)	C20—C21	1.525 (4)
C2—C3	1.377 (4)	C20—C24	1.535 (3)
C2—H2	0.9300	C20—H20	0.9800
C3—C4	1.381 (4)	C21—C22	1.531 (4)
C3—H3	0.9300	C21—H21A	0.9700
C4—C5	1.377 (3)	C21—H21B	0.9700
C4—H4	0.9300	C22—H22A	0.9700
C5—C6	1.394 (3)	C22—H22B	0.9700
C5—H5	0.9300	C23—C24	1.558 (3)
C6—C7	1.455 (3)	C23—H23A	0.9700
C7—H7	0.9300	C23—H23B	0.9700
C8—C9	1.524 (3)	C24—C25	1.498 (4)
C8—C18	1.537 (3)	C24—H24	0.9800
C8—H8	0.9800	C25—C26	1.293 (4)
C9—C10	1.369 (3)	C25—H25	0.9300
C9—C17	1.428 (3)	C26—H26A	0.9300
C10—C11	1.394 (3)	C26—H26B	0.9300
C10—H10	0.9300	C27—H27A	0.9600
C11—H11	0.9300	C27—H27B	0.9600
C12—C13	1.408 (3)	C27—H27C	0.9600
C12—C17	1.426 (3)
C7—N1—C8	118.14 (18)	C16—C17—C12	118.01 (18)
C11—N2—C12	116.44 (19)	C16—C17—C9	124.77 (17)
C18—N3—C22	111.69 (17)	C12—C17—C9	117.22 (18)
C18—N3—C23	107.62 (18)	N3—C18—C8	112.13 (17)
C22—N3—C23	107.80 (17)	N3—C18—C19	111.27 (17)
C1—O1—H1	109.5	C8—C18—C19	111.09 (16)
C15—O2—C27	119.3 (2)	N3—C18—H18	107.4
O1—C1—C2	118.6 (2)	C8—C18—H18	107.4
O1—C1—C6	121.00 (18)	C19—C18—H18	107.4
C2—C1—C6	120.4 (2)	C20—C19—C18	108.15 (19)
C3—C2—C1	119.6 (2)	C20—C19—H19A	110.1
C3—C2—H2	120.2	C18—C19—H19A	110.1
C1—C2—H2	120.2	C20—C19—H19B	110.1
C2—C3—C4	121.1 (2)	C18—C19—H19B	110.1
C2—C3—H3	119.4	H19A—C19—H19B	108.4
C4—C3—H3	119.4	C21—C20—C19	107.9 (2)
C5—C4—C3	119.2 (2)	C21—C20—C24	108.6 (2)
C5—C4—H4	120.4	C19—C20—C24	110.6 (2)
C3—C4—H4	120.4	C21—C20—H20	109.9
C4—C5—C6	121.1 (2)	C19—C20—H20	109.9
C4—C5—H5	119.5	C24—C20—H20	109.9
C6—C5—H5	119.5	C20—C21—C22	108.5 (2)
C5—C6—C1	118.5 (2)	C20—C21—H21A	110.0
C5—C6—C7	120.0 (2)	C22—C21—H21A	110.0
C1—C6—C7	121.46 (19)	C20—C21—H21B	110.0
N1—C7—C6	122.49 (19)	C22—C21—H21B	110.0
N1—C7—H7	118.8	H21A—C21—H21B	108.4
C6—C7—H7	118.8	N3—C22—C21	111.8 (2)
N1—C8—C9	107.63 (15)	N3—C22—H22A	109.2
N1—C8—C18	110.92 (15)	C21—C22—H22A	109.2
C9—C8—C18	109.15 (16)	N3—C22—H22B	109.2
N1—C8—H8	109.7	C21—C22—H22B	109.2
C9—C8—H8	109.7	H22A—C22—H22B	107.9
C18—C8—H8	109.7	N3—C23—C24	112.82 (18)
C10—C9—C17	117.65 (18)	N3—C23—H23A	109.0
C10—C9—C8	119.18 (18)	C24—C23—H23A	109.0
C17—C9—C8	123.17 (17)	N3—C23—H23B	109.0
C9—C10—C11	120.6 (2)	C24—C23—H23B	109.0
C9—C10—H10	119.7	H23A—C23—H23B	107.8
C11—C10—H10	119.7	C25—C24—C20	114.0 (2)
N2—C11—C10	124.5 (2)	C25—C24—C23	111.8 (2)
N2—C11—H11	117.7	C20—C24—C23	106.36 (18)
C10—C11—H11	117.7	C25—C24—H24	108.2
N2—C12—C13	117.4 (2)	C20—C24—H24	108.2
N2—C12—C17	123.57 (19)	C23—C24—H24	108.2
C13—C12—C17	119.0 (2)	C26—C25—C24	126.5 (3)
C14—C13—C12	121.5 (2)	C26—C25—H25	116.8
C14—C13—H13	119.2	C24—C25—H25	116.8
C12—C13—H13	119.2	C25—C26—H26A	120.0
C13—C14—C15	119.8 (2)	C25—C26—H26B	120.0
C13—C14—H14	120.1	H26A—C26—H26B	120.0
C15—C14—H14	120.1	O2—C27—H27A	109.5
C16—C15—O2	115.9 (2)	O2—C27—H27B	109.5
C16—C15—C14	120.6 (2)	H27A—C27—H27B	109.5
O2—C15—C14	123.51 (18)	O2—C27—H27C	109.5
C15—C16—C17	121.0 (2)	H27A—C27—H27C	109.5
C15—C16—H16	119.5	H27B—C27—H27C	109.5
C17—C16—H16	119.5
O1—C1—C2—C3	−179.6 (2)	C15—C16—C17—C9	179.84 (19)
C6—C1—C2—C3	0.2 (4)	N2—C12—C17—C16	178.52 (19)
C1—C2—C3—C4	−0.4 (4)	C13—C12—C17—C16	−1.9 (3)
C2—C3—C4—C5	0.5 (4)	N2—C12—C17—C9	−0.9 (3)
C3—C4—C5—C6	−0.4 (4)	C13—C12—C17—C9	178.69 (19)
C4—C5—C6—C1	0.2 (3)	C10—C9—C17—C16	−177.42 (18)
C4—C5—C6—C7	−179.6 (2)	C8—C9—C17—C16	2.7 (3)
O1—C1—C6—C5	179.7 (2)	C10—C9—C17—C12	1.9 (3)
C2—C1—C6—C5	−0.2 (3)	C8—C9—C17—C12	−177.90 (17)
O1—C1—C6—C7	−0.5 (3)	C22—N3—C18—C8	67.6 (2)
C2—C1—C6—C7	179.7 (2)	C23—N3—C18—C8	−174.22 (17)
C8—N1—C7—C6	−176.87 (16)	C22—N3—C18—C19	−57.5 (2)
C5—C6—C7—N1	178.6 (2)	C23—N3—C18—C19	60.7 (2)
C1—C6—C7—N1	−1.3 (3)	N1—C8—C18—N3	53.4 (2)
C7—N1—C8—C9	109.5 (2)	C9—C8—C18—N3	171.84 (16)
C7—N1—C8—C18	−131.2 (2)	N1—C8—C18—C19	178.63 (18)
N1—C8—C9—C10	54.8 (2)	C9—C8—C18—C19	−63.0 (2)
C18—C8—C9—C10	−65.7 (2)	N3—C18—C19—C20	−0.7 (3)
N1—C8—C9—C17	−125.40 (19)	C8—C18—C19—C20	−126.4 (2)
C18—C8—C9—C17	114.15 (19)	C18—C19—C20—C21	59.8 (3)
C17—C9—C10—C11	−1.5 (3)	C18—C19—C20—C24	−58.9 (3)
C8—C9—C10—C11	178.35 (19)	C19—C20—C21—C22	−62.9 (3)
C12—N2—C11—C10	1.3 (3)	C24—C20—C21—C22	57.0 (3)
C9—C10—C11—N2	−0.2 (3)	C18—N3—C22—C21	54.8 (3)
C11—N2—C12—C13	179.7 (2)	C23—N3—C22—C21	−63.2 (2)
C11—N2—C12—C17	−0.7 (3)	C20—C21—C22—N3	5.9 (3)
N2—C12—C13—C14	−178.8 (2)	C18—N3—C23—C24	−63.8 (2)
C17—C12—C13—C14	1.6 (3)	C22—N3—C23—C24	56.8 (3)
C12—C13—C14—C15	0.3 (3)	C21—C20—C24—C25	174.1 (2)
C27—O2—C15—C16	174.0 (2)	C19—C20—C24—C25	−67.7 (3)
C27—O2—C15—C14	−5.4 (3)	C21—C20—C24—C23	−62.3 (3)
C13—C14—C15—C16	−1.8 (3)	C19—C20—C24—C23	56.0 (3)
C13—C14—C15—O2	177.6 (2)	N3—C23—C24—C25	129.9 (2)
O2—C15—C16—C17	−178.10 (18)	N3—C23—C24—C20	4.9 (3)
C14—C15—C16—C17	1.4 (3)	C20—C24—C25—C26	−116.8 (3)
C15—C16—C17—C12	0.5 (3)	C23—C24—C25—C26	122.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.605 (2)	148.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.605 (2)	148