1-Ethyl-4-hydr-oxy-9-aza-tricyclo-[7.4.1.0]tetra-deca-2,4,6-trien-8-one.

In the mol-ecule of the title compound, C(15)H(19)NO(2), the six-membered dihydro-pyridinone ring assumes a screw-boat conformation. In the crystal structure, mol-ecules are linked via O-H⋯O hydrogen bonding between hydr-oxy and carbonyl groups, forming supra-molecular chains along the a axis.

Related literature

For the synthesis and bioactivity of novel bis-(−)-nor-meptazinols, see Xie et al. (2008 ▶).

Experimental

Crystal data

C15H19NO2

M = 245.31

Orthorhombic,

a = 8.298 (1) Å

b = 9.9817 (12) Å

c = 14.7324 (18) Å

V = 1220.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.37 × 0.23 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

6713 measured reflections

1397 independent reflections

1280 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.091

S = 1.06

1397 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903918X/xu2615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903918X/xu2615Isup2.hkl

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

C15H19NO2	F(000) = 528
Mr = 245.31	Dx = 1.335 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2536 reflections
a = 8.298 (1) Å	θ = 2.5–26.4°
b = 9.9817 (12) Å	µ = 0.09 mm−1
c = 14.7324 (18) Å	T = 293 K
V = 1220.3 (3) Å3	Prismatic, colourless
Z = 4	0.37 × 0.23 × 0.22 mm

Bruker SMART APEX CCD area-detector diffractometer	1280 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
graphite	θmax = 26.0°, θmin = 2.5°
φ and ω scans	h = −10→10
6713 measured reflections	k = −12→12
1397 independent reflections	l = −11→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0557P)2] where P = (Fo2 + 2Fc2)/3
1397 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.20 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
N1	1.0502 (2)	0.76044 (17)	0.90237 (11)	0.0315 (4)
O1	1.16080 (18)	0.96697 (17)	0.91934 (11)	0.0429 (4)
O2	0.4251 (2)	1.11984 (16)	0.94981 (13)	0.0507 (5)
H2	0.3557	1.0686	0.9307	0.076*
C1	1.0402 (2)	0.8931 (2)	0.91820 (13)	0.0301 (5)
C2	0.8763 (2)	0.9473 (2)	0.93043 (13)	0.0285 (5)
C3	0.8531 (3)	1.0689 (2)	0.97449 (13)	0.0328 (5)
H3	0.9410	1.1126	1.0001	0.039*
C4	0.7027 (3)	1.1258 (2)	0.98083 (14)	0.0357 (5)
H4	0.6883	1.2061	1.0118	0.043*
C5	0.5729 (3)	1.0620 (2)	0.94053 (15)	0.0336 (5)
C6	0.5946 (3)	0.9430 (2)	0.89339 (14)	0.0310 (5)
H6	0.5072	0.9031	0.8646	0.037*
C7	0.7454 (2)	0.8827 (2)	0.88863 (12)	0.0262 (4)
C8	0.7732 (2)	0.7468 (2)	0.84288 (13)	0.0279 (4)
C9	0.9025 (3)	0.67983 (19)	0.90089 (14)	0.0312 (5)
H9A	0.8627	0.6687	0.9623	0.037*
H9B	0.9263	0.5917	0.8766	0.037*
C10	1.1831 (3)	0.7095 (2)	0.84858 (15)	0.0416 (6)
H10A	1.2152	0.6222	0.8711	0.050*
H10B	1.2747	0.7694	0.8537	0.050*
C11	1.1318 (3)	0.6983 (2)	0.74892 (15)	0.0431 (6)
H11A	1.2261	0.7101	0.7108	0.052*
H11B	1.0905	0.6087	0.7382	0.052*
C12	1.0037 (3)	0.7998 (2)	0.72030 (14)	0.0386 (6)
H12A	1.0121	0.8133	0.6553	0.046*
H12B	1.0277	0.8847	0.7494	0.046*
C13	0.8296 (3)	0.7620 (2)	0.74266 (13)	0.0336 (5)
H13A	0.8074	0.6777	0.7124	0.040*
H13B	0.7609	0.8288	0.7146	0.040*
C14	0.6173 (3)	0.6630 (2)	0.84401 (15)	0.0351 (5)
H14A	0.5664	0.6741	0.9028	0.042*
H14B	0.5444	0.6993	0.7988	0.042*
C15	0.6367 (3)	0.5130 (2)	0.82599 (18)	0.0477 (6)
H15A	0.6932	0.5000	0.7698	0.072*
H15B	0.5323	0.4719	0.8223	0.072*
H15C	0.6968	0.4729	0.8746	0.072*

	U11	U22	U33	U12	U13	U23
N1	0.0219 (9)	0.0378 (9)	0.0348 (9)	0.0014 (8)	−0.0012 (7)	−0.0003 (8)
O1	0.0258 (8)	0.0495 (9)	0.0534 (9)	−0.0093 (7)	−0.0018 (7)	−0.0064 (8)
O2	0.0298 (9)	0.0380 (9)	0.0842 (13)	0.0030 (8)	0.0012 (9)	−0.0190 (9)
C1	0.0256 (11)	0.0373 (11)	0.0273 (10)	−0.0054 (9)	−0.0036 (9)	−0.0018 (9)
C2	0.0254 (11)	0.0343 (11)	0.0259 (9)	−0.0029 (9)	−0.0007 (8)	0.0007 (8)
C3	0.0286 (11)	0.0367 (11)	0.0330 (10)	−0.0075 (10)	−0.0013 (9)	−0.0048 (9)
C4	0.0375 (13)	0.0308 (11)	0.0387 (11)	−0.0019 (10)	0.0035 (10)	−0.0071 (9)
C5	0.0287 (11)	0.0301 (10)	0.0421 (12)	−0.0003 (10)	0.0040 (9)	−0.0020 (9)
C6	0.0243 (11)	0.0315 (10)	0.0371 (11)	−0.0044 (9)	−0.0026 (9)	−0.0034 (9)
C7	0.0247 (11)	0.0311 (10)	0.0229 (9)	−0.0037 (9)	0.0012 (8)	0.0012 (8)
C8	0.0239 (11)	0.0322 (10)	0.0276 (9)	−0.0013 (9)	−0.0003 (8)	−0.0035 (8)
C9	0.0294 (11)	0.0303 (10)	0.0338 (11)	−0.0018 (9)	−0.0003 (9)	−0.0007 (9)
C10	0.0241 (12)	0.0475 (13)	0.0532 (14)	0.0042 (10)	0.0015 (10)	−0.0066 (11)
C11	0.0361 (14)	0.0462 (12)	0.0470 (13)	0.0007 (11)	0.0124 (11)	−0.0097 (11)
C12	0.0425 (14)	0.0433 (12)	0.0302 (10)	−0.0039 (12)	0.0068 (10)	−0.0011 (9)
C13	0.0328 (12)	0.0406 (11)	0.0274 (10)	−0.0005 (10)	−0.0011 (9)	−0.0042 (9)
C14	0.0271 (12)	0.0391 (11)	0.0390 (11)	−0.0039 (10)	0.0015 (10)	−0.0078 (9)
C15	0.0402 (15)	0.0392 (12)	0.0637 (15)	−0.0090 (11)	0.0056 (12)	−0.0131 (11)

N1—C1	1.347 (3)	C9—H9A	0.9700
N1—C10	1.451 (3)	C9—H9B	0.9700
N1—C9	1.466 (3)	C10—C11	1.533 (3)
O1—C1	1.243 (2)	C10—H10A	0.9700
O2—C5	1.362 (3)	C10—H10B	0.9700
O2—H2	0.8200	C11—C12	1.528 (3)
C1—C2	1.475 (3)	C11—H11A	0.9700
C2—C3	1.390 (3)	C11—H11B	0.9700
C2—C7	1.406 (3)	C12—C13	1.529 (3)
C3—C4	1.375 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.385 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.387 (3)	C14—C15	1.529 (3)
C6—C7	1.391 (3)	C14—H14A	0.9700
C6—H6	0.9300	C14—H14B	0.9700
C7—C8	1.532 (3)	C15—H15A	0.9600
C8—C9	1.526 (3)	C15—H15B	0.9600
C8—C14	1.541 (3)	C15—H15C	0.9600
C8—C13	1.556 (3)
C1—N1—C10	119.04 (19)	N1—C10—C11	109.72 (18)
C1—N1—C9	119.42 (17)	N1—C10—H10A	109.7
C10—N1—C9	115.80 (16)	C11—C10—H10A	109.7
C5—O2—H2	109.5	N1—C10—H10B	109.7
O1—C1—N1	122.43 (19)	C11—C10—H10B	109.7
O1—C1—C2	121.54 (18)	H10A—C10—H10B	108.2
N1—C1—C2	115.98 (18)	C12—C11—C10	114.14 (17)
C3—C2—C7	119.91 (19)	C12—C11—H11A	108.7
C3—C2—C1	120.34 (18)	C10—C11—H11A	108.7
C7—C2—C1	119.38 (17)	C12—C11—H11B	108.7
C4—C3—C2	121.2 (2)	C10—C11—H11B	108.7
C4—C3—H3	119.4	H11A—C11—H11B	107.6
C2—C3—H3	119.4	C11—C12—C13	115.73 (18)
C3—C4—C5	119.17 (18)	C11—C12—H12A	108.3
C3—C4—H4	120.4	C13—C12—H12A	108.3
C5—C4—H4	120.4	C11—C12—H12B	108.3
O2—C5—C4	117.53 (18)	C13—C12—H12B	108.3
O2—C5—C6	122.03 (19)	H12A—C12—H12B	107.4
C4—C5—C6	120.4 (2)	C12—C13—C8	120.83 (17)
C5—C6—C7	120.88 (19)	C12—C13—H13A	107.1
C5—C6—H6	119.6	C8—C13—H13A	107.1
C7—C6—H6	119.6	C12—C13—H13B	107.1
C6—C7—C2	118.32 (17)	C8—C13—H13B	107.1
C6—C7—C8	122.77 (18)	H13A—C13—H13B	106.8
C2—C7—C8	118.88 (18)	C15—C14—C8	116.17 (18)
C9—C8—C7	104.31 (15)	C15—C14—H14A	108.2
C9—C8—C14	110.29 (16)	C8—C14—H14A	108.2
C7—C8—C14	110.45 (16)	C15—C14—H14B	108.2
C9—C8—C13	111.28 (17)	C8—C14—H14B	108.2
C7—C8—C13	112.08 (17)	H14A—C14—H14B	107.4
C14—C8—C13	108.41 (16)	C14—C15—H15A	109.5
N1—C9—C8	110.83 (15)	C14—C15—H15B	109.5
N1—C9—H9A	109.5	H15A—C15—H15B	109.5
C8—C9—H9A	109.5	C14—C15—H15C	109.5
N1—C9—H9B	109.5	H15A—C15—H15C	109.5
C8—C9—H9B	109.5	H15B—C15—H15C	109.5
H9A—C9—H9B	108.1
C10—N1—C1—O1	−27.0 (3)	C2—C7—C8—C9	33.5 (2)
C9—N1—C1—O1	−179.22 (17)	C6—C7—C8—C14	−25.7 (2)
C10—N1—C1—C2	150.53 (17)	C2—C7—C8—C14	152.04 (18)
C9—N1—C1—C2	−1.7 (3)	C6—C7—C8—C13	95.3 (2)
O1—C1—C2—C3	−23.0 (3)	C2—C7—C8—C13	−87.0 (2)
N1—C1—C2—C3	159.45 (18)	C1—N1—C9—C8	47.4 (2)
O1—C1—C2—C7	150.1 (2)	C10—N1—C9—C8	−105.69 (19)
N1—C1—C2—C7	−27.5 (3)	C7—C8—C9—N1	−59.9 (2)
C7—C2—C3—C4	2.2 (3)	C14—C8—C9—N1	−178.47 (15)
C1—C2—C3—C4	175.27 (19)	C13—C8—C9—N1	61.2 (2)
C2—C3—C4—C5	−1.6 (3)	C1—N1—C10—C11	−94.0 (2)
C3—C4—C5—O2	178.7 (2)	C9—N1—C10—C11	59.2 (2)
C3—C4—C5—C6	−0.8 (3)	N1—C10—C11—C12	29.3 (3)
O2—C5—C6—C7	−176.9 (2)	C10—C11—C12—C13	−82.8 (2)
C4—C5—C6—C7	2.6 (3)	C11—C12—C13—C8	63.9 (3)
C5—C6—C7—C2	−1.9 (3)	C9—C8—C13—C12	−39.0 (3)
C5—C6—C7—C8	175.79 (18)	C7—C8—C13—C12	77.3 (2)
C3—C2—C7—C6	−0.5 (3)	C14—C8—C13—C12	−160.48 (18)
C1—C2—C7—C6	−173.55 (19)	C9—C8—C14—C15	−48.4 (3)
C3—C2—C7—C8	−178.25 (17)	C7—C8—C14—C15	−163.21 (19)
C1—C2—C7—C8	8.6 (3)	C13—C8—C14—C15	73.6 (2)
C6—C7—C8—C9	−144.15 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.92	2.710 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.92	2.710 (2)	162

Symmetry code: (i) .