[1-Meth-oxy-3-(pyridin-2-yl)indolizin-2-yl](pyridin-2-yl)methanone.

Methyl-ation of [1-hy-droxy-3-(pyridin-2-yl)indolizin-2-yl](pyridin-2-yl)methanone was performed via metalation with potassium tert-butano-late in toluene and a subsequent metathesis reaction with methyl iodide yielded the yellow title compound, C(20)H(15)N(3)O(2). The substituents at the indolizine unit are twisted [the indolizine ring system makes dihedral angles of 34.67 (7) and 77.49 (5)°, respectively, with the pyridyl and pyridinoyl rings] with single bonds between the central unit and the attached pyridine ring [1.459 (3) Å] and the pyridinoyl group [1.483 (3) Å]. There are no classical hydrogen bonds in the crystal structure.

Related literature

Indolizines are used as dyes (Weidner et al., 1989 ▶), pharmaceuticals (Singh & Mmatli, 2011 ▶), and spectroscopic sensitizers (Gilchrist, 2001 ▶; Katrizky et al., 1999 ▶; Sarkunam & Nallu, 2005 ▶; Vemula et al., 2011 ▶; Weeler, 1985a ▶,b ▶). Indolizines are rather scarce in nature whereas the reduced form of these heteroaromatic bicyclic compounds, the indolizidines, are quite common, see: Michael (2007 ▶) and references therein. Well defined substitution patterns are required (Sarkunam & Nallu, 2005 ▶; Swinbourne et al., 1978 ▶; Uchida & Matsumoto, 1976 ▶) and therefore, different transition-metal mediated and metal-free strategies for the synthesis of substituted indolizines have been developed (Jacobs et al., 2011 ▶; Swinbourne et al., 1978 ▶; Kel’in et al., 2001 ▶; Kim et al., 2010 ▶; Liu et al., 2007 ▶; Morra et al., 2006 ▶; Seregin & Gevorgyan, 2006 ▶; Yan & Liu, 2007 ▶). Pyridinium N-methyl­ides react with acetyl­enes or with ethyl­enes in the presence of an oxidant to make indolizines (Miki et al., 1984 ▶; Padwa et al., 1993; ▶ Wei et al., 1993 ▶). For cyclization of 1,1-diacetyl-2-(2-pyrid­yl)ethyl­ene in acetic acid anhydride or in dimethyl­sulfoxide-yielding indolizines, see: Pohjala (1974 ▶, 1977 ▶).

Experimental

Crystal data

C20H15N3O2

M = 329.35

Monoclinic,

a = 25.822 (2) Å

b = 11.4406 (9) Å

c = 11.3602 (7) Å

β = 107.070 (4)°

V = 3208.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 183 K

0.05 × 0.05 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

10598 measured reflections

3667 independent reflections

2207 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.132

S = 1.03

3667 reflections

275 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski, Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203396X/gg2090sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203396X/gg2090Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203396X/gg2090Isup3.cml

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

C20H15N3O2	F(000) = 1376
Mr = 329.35	Dx = 1.364 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 10598 reflections
a = 25.822 (2) Å	θ = 1.7–27.5°
b = 11.4406 (9) Å	µ = 0.09 mm−1
c = 11.3602 (7) Å	T = 183 K
β = 107.070 (4)°	Prism, brown
V = 3208.2 (4) Å3	0.05 × 0.05 × 0.05 mm
Z = 8

Nonius KappaCCD diffractometer	2207 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.070
Graphite monochromator	θmax = 27.5°, θmin = 1.7°
phi– + ω–scan	h = −29→33
10598 measured reflections	k = −14→14
3667 independent reflections	l = −14→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0651P)2] where P = (Fo2 + 2Fc2)/3
3667 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
O1	0.04698 (6)	0.09288 (12)	0.06993 (13)	0.0364 (4)
O2	0.12184 (6)	0.12783 (12)	0.35467 (12)	0.0383 (4)
N1	0.15233 (6)	0.26387 (13)	0.01130 (13)	0.0259 (4)
N2	0.22178 (7)	0.32179 (13)	0.33083 (14)	0.0285 (4)
N3	0.08352 (7)	0.41960 (14)	0.28790 (15)	0.0348 (4)
C1	0.18167 (9)	0.29453 (18)	−0.06859 (18)	0.0315 (5)
H1	0.2132 (10)	0.3465 (18)	−0.0350 (19)	0.042 (6)*
C2	0.16708 (9)	0.25249 (19)	−0.18445 (19)	0.0365 (5)
H2	0.1893 (9)	0.2805 (18)	−0.238 (2)	0.042 (6)*
C3	0.12207 (10)	0.17639 (19)	−0.22799 (19)	0.0381 (5)
H3	0.1124 (9)	0.1416 (18)	−0.313 (2)	0.039 (6)*
C4	0.09303 (9)	0.14572 (17)	−0.15113 (17)	0.0328 (5)
H4	0.0638 (9)	0.0923 (18)	−0.1749 (18)	0.032 (6)*
C5	0.10777 (8)	0.18737 (16)	−0.02876 (17)	0.0272 (4)
C6	0.08989 (8)	0.16467 (15)	0.07313 (17)	0.0276 (4)
C7	0.12235 (8)	0.22698 (15)	0.17367 (16)	0.0254 (4)
C8	0.16079 (8)	0.28941 (15)	0.13492 (16)	0.0248 (4)
C9	0.20472 (8)	0.35985 (16)	0.21281 (16)	0.0265 (4)
C10	0.22672 (9)	0.45894 (18)	0.17435 (19)	0.0323 (5)
H10	0.2123 (9)	0.4926 (19)	0.095 (2)	0.041 (6)*
C11	0.26848 (9)	0.51716 (19)	0.2576 (2)	0.0388 (5)
H11	0.2828 (9)	0.5875 (19)	0.2335 (19)	0.045 (6)*
C12	0.28677 (9)	0.47791 (19)	0.3779 (2)	0.0383 (5)
H12	0.3157 (10)	0.513 (2)	0.442 (2)	0.060 (7)*
C13	0.26168 (8)	0.38150 (18)	0.40973 (18)	0.0328 (5)
H13	0.2725 (8)	0.3486 (16)	0.4960 (19)	0.033 (5)*
C14	0.11818 (8)	0.22114 (17)	0.30094 (17)	0.0270 (4)
C15	0.10492 (8)	0.32971 (16)	0.36106 (16)	0.0271 (4)
C16	0.11300 (9)	0.3300 (2)	0.48702 (19)	0.0372 (5)
H16	0.1298 (9)	0.2654 (18)	0.5342 (18)	0.031 (5)*
C17	0.09646 (10)	0.4251 (2)	0.5409 (2)	0.0424 (6)
H17	0.1002 (10)	0.425 (2)	0.629 (2)	0.053 (7)*
C18	0.07292 (9)	0.5171 (2)	0.4673 (2)	0.0404 (6)
H18	0.0603 (9)	0.5834 (19)	0.500 (2)	0.045 (6)*
C19	0.06806 (10)	0.5113 (2)	0.3431 (2)	0.0423 (6)
H19	0.0544 (10)	0.576 (2)	0.290 (2)	0.056 (7)*
C20	−0.00098 (11)	0.1550 (2)	0.0648 (3)	0.0683 (8)
H20C	−0.0300	0.0995	0.0643	0.102*
H20B	−0.0117	0.2023	−0.0104	0.102*
H20A	0.0055	0.2061	0.1369	0.102*

	U11	U22	U33	U12	U13	U23
O1	0.0330 (9)	0.0298 (8)	0.0470 (9)	−0.0081 (6)	0.0125 (7)	−0.0046 (6)
O2	0.0521 (10)	0.0285 (8)	0.0367 (8)	−0.0005 (7)	0.0169 (7)	0.0041 (6)
N1	0.0272 (9)	0.0271 (9)	0.0239 (8)	0.0024 (7)	0.0082 (7)	0.0018 (7)
N2	0.0298 (10)	0.0293 (8)	0.0260 (8)	−0.0013 (7)	0.0074 (7)	−0.0022 (7)
N3	0.0443 (11)	0.0292 (9)	0.0332 (9)	0.0047 (8)	0.0151 (8)	0.0022 (8)
C1	0.0309 (12)	0.0356 (12)	0.0302 (11)	0.0044 (10)	0.0123 (9)	0.0043 (9)
C2	0.0423 (13)	0.0419 (13)	0.0286 (11)	0.0085 (10)	0.0154 (10)	0.0058 (10)
C3	0.0507 (15)	0.0377 (12)	0.0248 (11)	0.0066 (11)	0.0091 (10)	−0.0013 (9)
C4	0.0414 (14)	0.0261 (11)	0.0272 (11)	0.0018 (10)	0.0042 (9)	−0.0014 (9)
C5	0.0292 (11)	0.0221 (9)	0.0290 (10)	0.0023 (8)	0.0067 (8)	−0.0016 (8)
C6	0.0280 (11)	0.0221 (10)	0.0326 (10)	0.0002 (8)	0.0087 (8)	−0.0015 (8)
C7	0.0273 (11)	0.0215 (9)	0.0272 (10)	0.0026 (8)	0.0079 (8)	0.0003 (8)
C8	0.0279 (11)	0.0203 (9)	0.0255 (9)	0.0010 (8)	0.0068 (8)	−0.0004 (8)
C9	0.0289 (11)	0.0256 (10)	0.0266 (10)	0.0021 (8)	0.0105 (8)	−0.0015 (8)
C10	0.0352 (12)	0.0305 (11)	0.0325 (11)	−0.0017 (9)	0.0119 (9)	0.0029 (9)
C11	0.0369 (13)	0.0300 (11)	0.0514 (14)	−0.0090 (10)	0.0159 (10)	−0.0018 (10)
C12	0.0356 (13)	0.0374 (12)	0.0399 (12)	−0.0067 (10)	0.0080 (10)	−0.0084 (10)
C13	0.0347 (13)	0.0337 (11)	0.0289 (11)	−0.0004 (9)	0.0076 (9)	−0.0032 (9)
C14	0.0263 (11)	0.0260 (10)	0.0282 (10)	−0.0023 (8)	0.0070 (8)	0.0019 (8)
C15	0.0280 (11)	0.0258 (10)	0.0297 (10)	−0.0048 (8)	0.0119 (8)	−0.0003 (8)
C16	0.0452 (14)	0.0382 (12)	0.0295 (11)	−0.0028 (11)	0.0129 (10)	0.0017 (10)
C17	0.0554 (16)	0.0420 (13)	0.0342 (12)	−0.0089 (11)	0.0199 (11)	−0.0096 (11)
C18	0.0443 (14)	0.0343 (12)	0.0492 (14)	−0.0100 (11)	0.0241 (11)	−0.0168 (11)
C19	0.0497 (15)	0.0322 (12)	0.0485 (14)	0.0073 (11)	0.0202 (11)	0.0026 (11)
C20	0.0404 (16)	0.0635 (18)	0.109 (2)	−0.0123 (14)	0.0349 (15)	−0.0344 (16)

O1—C6	1.371 (2)	C8—C9	1.459 (3)
O1—C20	1.414 (3)	C9—C10	1.395 (3)
O2—C14	1.220 (2)	C10—C11	1.379 (3)
N1—C1	1.387 (2)	C10—H10	0.95 (2)
N1—C8	1.387 (2)	C11—C12	1.383 (3)
N1—C5	1.411 (2)	C11—H11	0.96 (2)
N2—C13	1.338 (2)	C12—C13	1.380 (3)
N2—C9	1.354 (2)	C12—H12	0.97 (2)
N3—C15	1.336 (2)	C13—H13	1.01 (2)
N3—C19	1.341 (3)	C14—C15	1.505 (3)
C1—C2	1.347 (3)	C15—C16	1.384 (3)
C1—H1	0.99 (2)	C16—C17	1.376 (3)
C2—C3	1.420 (3)	C16—H16	0.94 (2)
C2—H2	1.00 (2)	C17—C18	1.371 (3)
C3—C4	1.353 (3)	C17—H17	0.98 (2)
C3—H3	1.01 (2)	C18—C19	1.382 (3)
C4—C5	1.412 (3)	C18—H18	0.94 (2)
C4—H4	0.95 (2)	C19—H19	0.96 (3)
C5—C6	1.391 (3)	C20—H20C	0.9800
C6—C7	1.398 (3)	C20—H20B	0.9800
C7—C8	1.395 (3)	C20—H20A	0.9800
C7—C14	1.483 (3)
C6—O1—C20	113.04 (16)	C9—C10—H10	122.9 (13)
C1—N1—C8	130.92 (17)	C10—C11—C12	119.5 (2)
C1—N1—C5	119.75 (16)	C10—C11—H11	119.9 (13)
C8—N1—C5	109.17 (15)	C12—C11—H11	120.4 (13)
C13—N2—C9	117.51 (17)	C13—C12—C11	117.9 (2)
C15—N3—C19	115.91 (17)	C13—C12—H12	116.9 (14)
C2—C1—N1	119.9 (2)	C11—C12—H12	125.2 (14)
C2—C1—H1	123.6 (12)	N2—C13—C12	124.12 (19)
N1—C1—H1	116.4 (12)	N2—C13—H13	113.5 (11)
C1—C2—C3	121.7 (2)	C12—C13—H13	122.3 (11)
C1—C2—H2	115.6 (12)	O2—C14—C7	120.69 (17)
C3—C2—H2	122.7 (12)	O2—C14—C15	119.34 (17)
C4—C3—C2	119.1 (2)	C7—C14—C15	119.79 (16)
C4—C3—H3	119.4 (12)	N3—C15—C16	123.41 (18)
C2—C3—H3	121.5 (12)	N3—C15—C14	117.44 (16)
C3—C4—C5	120.5 (2)	C16—C15—C14	119.08 (18)
C3—C4—H4	122.0 (12)	C17—C16—C15	119.3 (2)
C5—C4—H4	117.4 (12)	C17—C16—H16	121.3 (12)
C6—C5—N1	106.62 (15)	C15—C16—H16	119.4 (12)
C6—C5—C4	134.18 (19)	C18—C17—C16	118.4 (2)
N1—C5—C4	119.05 (18)	C18—C17—H17	120.9 (14)
O1—C6—C5	123.57 (16)	C16—C17—H17	120.6 (14)
O1—C6—C7	127.84 (17)	C17—C18—C19	118.5 (2)
C5—C6—C7	108.59 (17)	C17—C18—H18	121.3 (13)
C8—C7—C6	108.36 (16)	C19—C18—H18	120.2 (13)
C8—C7—C14	126.37 (16)	N3—C19—C18	124.4 (2)
C6—C7—C14	125.17 (17)	N3—C19—H19	115.0 (14)
N1—C8—C7	107.24 (15)	C18—C19—H19	120.6 (14)
N1—C8—C9	126.40 (17)	O1—C20—H20C	109.5
C7—C8—C9	126.14 (16)	O1—C20—H20B	109.5
N2—C9—C10	121.83 (17)	H20C—C20—H20B	109.5
N2—C9—C8	113.07 (16)	O1—C20—H20A	109.5
C10—C9—C8	125.07 (17)	H20C—C20—H20A	109.5
C11—C10—C9	119.08 (19)	H20B—C20—H20A	109.5
C11—C10—H10	117.7 (13)