4-(2-Fluoro-phen-yl)-2-meth-oxy-5,6,7,8,9,10-hexa-hydro-cyclo-octa-[b]pyridine-3-carbo-nitrile.

In the title compound, C19H19FN2O, the cyclo-octene ring adopts a twisted boat-chair conformation. The dihedral angle between the plane of the fluorophenyl substituent and that of the pyridine ring is 76.39 (8)°. The F and ortho-H atoms of the fluoro-benzene ring are disordered, with occupancy factors of 0.226 (5) and 0.774 (5). In the crystal, no significant inter-actions are observed between the mol-ecules beyond van der Waals contacts.

Related literature

For the biological activities of substituted pyridine derivatives, see: Bossert & Vater (1989 ▶); Bossert et al. (1981 ▶); Wang et al. (1989 ▶); Alajarin et al. (1995 ▶). For similar structures, see: Ramesh et al. (2009a ▶,b ▶).

Experimental

Crystal data

C19H19FN2O

M = 310.36

Monoclinic,

a = 9.5219 (3) Å

b = 13.8808 (4) Å

c = 12.1140 (3) Å

β = 97.829 (1)°

V = 1586.20 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.28 × 0.25 × 0.23 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.981

37690 measured reflections

3475 independent reflections

2812 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.155

S = 1.08

3475 reflections

220 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.61 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016365/zq2223sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016365/zq2223Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016365/zq2223Isup3.cml

CCDC reference: 1013943

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H19FN2O	F(000) = 656
Mr = 310.36	Dx = 1.300 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2000 reflections
a = 9.5219 (3) Å	θ = 2–27°
b = 13.8808 (4) Å	µ = 0.09 mm−1
c = 12.1140 (3) Å	T = 293 K
β = 97.829 (1)°	Block, colourless
V = 1586.20 (8) Å3	0.28 × 0.25 × 0.23 mm
Z = 4

Bruker Kappa APEXII diffractometer	3475 independent reflections
Radiation source: fine-focus sealed tube	2812 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 0 pixels mm-1	θmax = 27.0°, θmin = 2.2°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
Tmin = 0.977, Tmax = 0.981	l = −15→15
37690 measured reflections

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.7644P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3475 reflections	Δρmax = 0.65 e Å−3
220 parameters	Δρmin = −0.61 e Å−3
10 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: 0.010 (2)

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	Occ. (<1)
C1	0.48826 (19)	0.14942 (13)	0.47836 (14)	0.0386 (4)
C2	0.5667 (2)	0.18410 (14)	0.38693 (15)	0.0454 (4)
H2A	0.5635	0.1344	0.3303	0.054*
H2B	0.6653	0.1942	0.4170	0.054*
C3	0.5073 (2)	0.27694 (16)	0.33279 (17)	0.0537 (5)
H3A	0.5695	0.2983	0.2806	0.064*
H3B	0.4156	0.2631	0.2903	0.064*
C4	0.4896 (2)	0.35887 (16)	0.41229 (19)	0.0575 (5)
H4A	0.4163	0.3413	0.4569	0.069*
H4B	0.4566	0.4152	0.3689	0.069*
C5	0.6229 (3)	0.38643 (15)	0.49078 (18)	0.0566 (5)
H5A	0.7047	0.3636	0.4588	0.068*
H5B	0.6286	0.4562	0.4943	0.068*
C6	0.6324 (3)	0.34781 (16)	0.60938 (18)	0.0593 (6)
H6A	0.5458	0.3651	0.6384	0.071*
H6B	0.7098	0.3807	0.6546	0.071*
C7	0.6549 (2)	0.23933 (16)	0.62511 (16)	0.0496 (5)
H7A	0.7308	0.2200	0.5839	0.059*
H7B	0.6871	0.2274	0.7034	0.059*
C8	0.52873 (18)	0.17526 (13)	0.58972 (14)	0.0384 (4)
C9	0.45081 (18)	0.13641 (12)	0.66895 (14)	0.0370 (4)
C10	0.33770 (18)	0.07500 (12)	0.63392 (14)	0.0380 (4)
C11	0.30274 (19)	0.05759 (13)	0.51926 (14)	0.0396 (4)
C12	0.2597 (2)	0.02745 (14)	0.71119 (15)	0.0438 (4)
C13	0.1466 (3)	−0.01094 (17)	0.37142 (17)	0.0565 (5)
H13A	0.0670	−0.0539	0.3596	0.085*
H13B	0.2237	−0.0373	0.3376	0.085*
H13C	0.1203	0.0505	0.3385	0.085*
C14	0.48547 (16)	0.15856 (14)	0.79050 (14)	0.0421 (4)
C15	0.55536 (16)	0.09561 (12)	0.86460 (16)	0.0557 (5)
H15	0.5783	0.0356	0.8380	0.067*	0.226 (5)
F1B	0.3841 (3)	0.3087 (4)	0.7588 (5)	0.115 (4)	0.226 (5)
C16	0.5944 (2)	0.1143 (2)	0.97544 (19)	0.0741 (8)
H16	0.6419	0.0686	1.0227	0.089*
C17	0.5606 (3)	0.2033 (3)	1.0142 (2)	0.0807 (9)
H17	0.5861	0.2185	1.0891	0.097*
C18	0.4901 (3)	0.2696 (2)	0.9439 (2)	0.0737 (8)
H18	0.4672	0.3296	0.9708	0.088*
C19	0.4532 (2)	0.24716 (17)	0.83331 (18)	0.0571 (5)
H19	0.4054	0.2926	0.7859	0.069*	0.774 (5)
F1A	0.5857 (2)	0.00848 (12)	0.82521 (14)	0.0769 (8)	0.774 (5)
N1	0.37525 (17)	0.09332 (11)	0.44417 (12)	0.0417 (4)
N2	0.1995 (2)	−0.01308 (16)	0.77174 (16)	0.0628 (5)
O1	0.18988 (15)	0.00092 (11)	0.48868 (11)	0.0518 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0420 (9)	0.0375 (9)	0.0364 (9)	0.0037 (7)	0.0055 (7)	0.0002 (7)
C2	0.0526 (11)	0.0467 (10)	0.0383 (9)	−0.0006 (8)	0.0116 (8)	−0.0020 (8)
C3	0.0626 (12)	0.0571 (12)	0.0401 (10)	−0.0043 (10)	0.0021 (9)	0.0066 (9)
C4	0.0647 (13)	0.0491 (11)	0.0588 (13)	0.0085 (10)	0.0090 (10)	0.0078 (10)
C5	0.0719 (14)	0.0432 (10)	0.0570 (12)	−0.0088 (10)	0.0170 (10)	−0.0035 (9)
C6	0.0699 (14)	0.0607 (13)	0.0486 (11)	−0.0243 (11)	0.0127 (10)	−0.0139 (10)
C7	0.0431 (10)	0.0664 (13)	0.0378 (9)	−0.0106 (9)	0.0002 (7)	0.0045 (9)
C8	0.0380 (9)	0.0400 (9)	0.0366 (8)	0.0014 (7)	0.0025 (7)	0.0022 (7)
C9	0.0380 (9)	0.0381 (8)	0.0340 (8)	0.0039 (7)	0.0019 (6)	0.0003 (7)
C10	0.0405 (9)	0.0383 (9)	0.0349 (8)	0.0019 (7)	0.0043 (7)	0.0005 (7)
C11	0.0427 (9)	0.0374 (9)	0.0374 (9)	−0.0001 (7)	0.0010 (7)	−0.0009 (7)
C12	0.0447 (10)	0.0489 (10)	0.0377 (9)	−0.0029 (8)	0.0058 (7)	−0.0039 (8)
C13	0.0626 (13)	0.0613 (13)	0.0414 (10)	−0.0116 (10)	−0.0081 (9)	−0.0042 (9)
C14	0.0396 (9)	0.0516 (10)	0.0350 (9)	−0.0050 (8)	0.0046 (7)	−0.0034 (7)
C15	0.0576 (12)	0.0679 (14)	0.0404 (10)	0.0027 (10)	0.0024 (9)	0.0012 (9)
F1B	0.133 (8)	0.091 (6)	0.122 (7)	0.054 (5)	0.026 (6)	−0.025 (5)
C16	0.0668 (15)	0.113 (2)	0.0402 (11)	−0.0049 (15)	−0.0012 (10)	0.0109 (13)
C17	0.0796 (17)	0.123 (3)	0.0404 (12)	−0.0294 (17)	0.0112 (11)	−0.0250 (15)
C18	0.0838 (17)	0.0808 (17)	0.0614 (15)	−0.0219 (14)	0.0281 (13)	−0.0317 (14)
C19	0.0610 (13)	0.0617 (13)	0.0516 (11)	−0.0084 (10)	0.0183 (10)	−0.0141 (10)
F1A	0.1046 (16)	0.0693 (12)	0.0548 (11)	0.0386 (10)	0.0034 (9)	0.0068 (8)
N1	0.0484 (9)	0.0409 (8)	0.0350 (7)	−0.0002 (6)	0.0034 (6)	−0.0010 (6)
N2	0.0648 (12)	0.0756 (13)	0.0504 (10)	−0.0147 (10)	0.0164 (9)	0.0009 (9)
O1	0.0554 (8)	0.0587 (8)	0.0388 (7)	−0.0169 (6)	−0.0025 (6)	−0.0006 (6)

C1—N1	1.347 (2)	C9—C14	1.496 (2)
C1—C8	1.398 (2)	C10—C11	1.404 (2)
C1—C2	1.497 (2)	C10—C12	1.433 (3)
C2—C3	1.520 (3)	C11—N1	1.312 (2)
C2—H2A	0.9700	C11—O1	1.342 (2)
C2—H2B	0.9700	C12—N2	1.139 (3)
C3—C4	1.514 (3)	C13—O1	1.434 (2)
C3—H3A	0.9700	C13—H13A	0.9600
C3—H3B	0.9700	C13—H13B	0.9600
C4—C5	1.527 (3)	C13—H13C	0.9600
C4—H4A	0.9700	C14—C15	1.360 (3)
C4—H4B	0.9700	C14—C19	1.385 (3)
C5—C6	1.524 (3)	C15—F1A	1.3459 (10)
C5—H5A	0.9700	C15—C16	1.368 (3)
C5—H5B	0.9700	C15—H15	0.9300
C6—C7	1.529 (3)	F1B—C19	1.3477 (10)
C6—H6A	0.9700	C16—C17	1.375 (4)
C6—H6B	0.9700	C16—H16	0.9300
C7—C8	1.509 (3)	C17—C18	1.367 (4)
C7—H7A	0.9700	C17—H17	0.9300
C7—H7B	0.9700	C18—C19	1.374 (3)
C8—C9	1.399 (2)	C18—H18	0.9300
C9—C10	1.394 (2)	C19—H19	0.9300
N1—C1—C8	123.26 (16)	C9—C8—C7	120.56 (15)
N1—C1—C2	114.61 (15)	C10—C9—C8	119.14 (15)
C8—C1—C2	122.11 (16)	C10—C9—C14	118.89 (15)
C1—C2—C3	113.46 (16)	C8—C9—C14	121.97 (15)
C1—C2—H2A	108.9	C9—C10—C11	118.40 (16)
C3—C2—H2A	108.9	C9—C10—C12	122.05 (16)
C1—C2—H2B	108.9	C11—C10—C12	119.52 (16)
C3—C2—H2B	108.9	N1—C11—O1	120.49 (16)
H2A—C2—H2B	107.7	N1—C11—C10	122.98 (16)
C4—C3—C2	115.43 (16)	O1—C11—C10	116.53 (16)
C4—C3—H3A	108.4	N2—C12—C10	177.8 (2)
C2—C3—H3A	108.4	O1—C13—H13A	109.5
C4—C3—H3B	108.4	O1—C13—H13B	109.5
C2—C3—H3B	108.4	H13A—C13—H13B	109.5
H3A—C3—H3B	107.5	O1—C13—H13C	109.5
C3—C4—C5	115.42 (19)	H13A—C13—H13C	109.5
C3—C4—H4A	108.4	H13B—C13—H13C	109.5
C5—C4—H4A	108.4	C15—C14—C19	115.90 (18)
C3—C4—H4B	108.4	C15—C14—C9	122.68 (17)
C5—C4—H4B	108.4	C19—C14—C9	121.36 (18)
H4A—C4—H4B	107.5	F1A—C15—C14	116.92 (17)
C6—C5—C4	115.89 (18)	F1A—C15—C16	118.4 (2)
C6—C5—H5A	108.3	C14—C15—C16	124.7 (2)
C4—C5—H5A	108.3	C14—C15—H15	117.7
C6—C5—H5B	108.3	C16—C15—H15	117.7
C4—C5—H5B	108.3	C15—C16—C17	117.5 (3)
H5A—C5—H5B	107.4	C15—C16—H16	121.3
C5—C6—C7	116.94 (17)	C17—C16—H16	121.3
C5—C6—H6A	108.1	C18—C17—C16	120.7 (2)
C7—C6—H6A	108.1	C18—C17—H17	119.7
C5—C6—H6B	108.1	C16—C17—H17	119.7
C7—C6—H6B	108.1	C17—C18—C19	119.5 (3)
H6A—C6—H6B	107.3	C17—C18—H18	120.2
C8—C7—C6	116.88 (17)	C19—C18—H18	120.2
C8—C7—H7A	108.1	F1B—C19—C18	123.1 (4)
C6—C7—H7A	108.1	F1B—C19—C14	115.2 (4)
C8—C7—H7B	108.1	C18—C19—C14	121.8 (2)
C6—C7—H7B	108.1	C18—C19—H19	119.1
H7A—C7—H7B	107.3	C14—C19—H19	119.1
C1—C8—C9	117.45 (16)	C11—N1—C1	118.64 (15)
C1—C8—C7	121.95 (16)	C11—O1—C13	116.85 (15)
N1—C1—C2—C3	87.0 (2)	C10—C9—C14—C15	77.10 (18)
C8—C1—C2—C3	−91.8 (2)	C8—C9—C14—C15	−102.71 (18)
C1—C2—C3—C4	52.0 (2)	C10—C9—C14—C19	−105.84 (18)
C2—C3—C4—C5	54.9 (3)	C8—C9—C14—C19	74.3 (2)
C3—C4—C5—C6	−100.7 (2)	C19—C14—C15—F1A	178.92 (13)
C4—C5—C6—C7	69.8 (3)	C9—C14—C15—F1A	−3.88 (17)
C5—C6—C7—C8	−74.8 (3)	C19—C14—C15—C16	−0.02 (14)
N1—C1—C8—C9	3.2 (3)	C9—C14—C15—C16	177.18 (17)
C2—C1—C8—C9	−178.04 (16)	F1A—C15—C16—C17	−179.13 (17)
N1—C1—C8—C7	−179.21 (17)	C14—C15—C16—C17	−0.2 (2)
C2—C1—C8—C7	−0.4 (3)	C15—C16—C17—C18	0.4 (3)
C6—C7—C8—C1	80.7 (2)	C16—C17—C18—C19	−0.3 (3)
C6—C7—C8—C9	−101.8 (2)	C17—C18—C19—F1B	−179.75 (17)
C1—C8—C9—C10	−0.3 (2)	C17—C18—C19—C14	0.1 (3)
C7—C8—C9—C10	−177.92 (17)	C15—C14—C19—F1B	179.93 (8)
C1—C8—C9—C14	179.53 (16)	C9—C14—C19—F1B	2.7 (2)
C7—C8—C9—C14	1.9 (3)	C15—C14—C19—C18	0.08 (18)
C8—C9—C10—C11	−2.5 (3)	C9—C14—C19—C18	−177.16 (17)
C14—C9—C10—C11	177.63 (16)	O1—C11—N1—C1	−179.64 (16)
C8—C9—C10—C12	175.57 (17)	C10—C11—N1—C1	−0.1 (3)
C14—C9—C10—C12	−4.2 (3)	C8—C1—N1—C11	−3.0 (3)
C9—C10—C11—N1	2.9 (3)	C2—C1—N1—C11	178.14 (16)
C12—C10—C11—N1	−175.29 (17)	N1—C11—O1—C13	−5.3 (3)
C9—C10—C11—O1	−177.58 (16)	C10—C11—O1—C13	175.14 (17)
C12—C10—C11—O1	4.2 (3)