6-Benzyl-6,7-dihydro-5H-pyrrolo-[3,4-b]pyridine-5,7-dione.

In the title compound, C(14)H(10)N(2)O(2), the dihedral angle between the heterocyclic ring system and the phenyl ring is 45.8 (5)°. Weak inter-molecular C-H⋯N hydrogen bonding is present in the crystal structure.

Related literature

The title compound is a key inter­mediate in the synthesis of the quinolone anti­biotic moxifloxacin [systematic name: 1-cyclo­propyl-7-[(1S,6S)-2,8-diaza­bicyclo­[4.3.0]non-8-yl]-6-fluoro-8-meth­oxy-4-oxo-quinoline-3-carb­oxy­lic acid], see: Petersen et al. (1993 ▶). For a related structure, see: Garduño-Beltrán et al. (2009 ▶).

Experimental

Crystal data

C14H10N2O2

M = 238.24

Monoclinic,

a = 11.8548 (6) Å

b = 12.3969 (8) Å

c = 8.1676 (4) Å

β = 107.45 (3)°

V = 1145.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.981, T max = 0.991

2087 measured reflections

2087 independent reflections

1100 reflections with I > 2σ(I)

R int = 0.045

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.174

S = 1.00

2087 reflections

163 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811041006/xu5342sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041006/xu5342Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041006/xu5342Isup3.cml

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

C14H10N2O2	F(000) = 496
Mr = 238.24	Dx = 1.382 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.8548 (6) Å	θ = 10–13°
b = 12.3969 (8) Å	µ = 0.10 mm−1
c = 8.1676 (4) Å	T = 293 K
β = 107.45 (3)°	Block, colorless
V = 1145.1 (2) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1100 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 25.4°, θmin = 1.8°
ω/2θ scans	h = −14→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
Tmin = 0.981, Tmax = 0.991	l = 0→9
2087 measured reflections	3 standard reflections every 200 reflections
2087 independent reflections	intensity decay: 1%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.082P)2] where P = (Fo2 + 2Fc2)/3
2087 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.17 e Å−3
12 restraints	Δρmin = −0.13 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	0.2267 (2)	0.6223 (2)	0.0923 (3)	0.0602 (7)
O1	0.20765 (18)	0.43903 (17)	0.1329 (3)	0.0753 (7)
C1	0.4977 (3)	0.7166 (3)	0.2368 (5)	0.0896 (11)
H1A	0.4640	0.7810	0.1871	0.108*
N2	−0.0141 (2)	0.74370 (19)	0.2194 (3)	0.0711 (7)
O2	0.19962 (18)	0.80705 (17)	0.0885 (3)	0.0782 (7)
C2	0.6005 (3)	0.7199 (3)	0.3733 (5)	0.0957 (12)
H2B	0.6327	0.7861	0.4170	0.115*
C3	0.6539 (3)	0.6287 (3)	0.4429 (4)	0.0763 (9)
H3A	0.7242	0.6307	0.5324	0.092*
C4	0.6038 (3)	0.5337 (3)	0.3807 (5)	0.0980 (13)
H4A	0.6398	0.4698	0.4289	0.118*
C5	0.5005 (3)	0.5297 (3)	0.2473 (5)	0.0919 (12)
H5A	0.4681	0.4630	0.2066	0.110*
C6	0.4446 (2)	0.6219 (2)	0.1734 (3)	0.0577 (8)
C7	0.3308 (3)	0.6186 (3)	0.0307 (4)	0.0758 (10)
H7A	0.3282	0.6793	−0.0454	0.091*
H7B	0.3282	0.5530	−0.0351	0.091*
C8	0.1751 (2)	0.5306 (2)	0.1379 (3)	0.0570 (8)
C9	0.0735 (2)	0.5705 (2)	0.1955 (3)	0.0505 (6)
C10	−0.0010 (2)	0.5161 (2)	0.2533 (3)	0.0493 (7)
H10A	0.0040	0.4415	0.2653	0.059*
C11	−0.0833 (3)	0.5716 (2)	0.2939 (4)	0.0655 (8)
H11A	−0.1372	0.5342	0.3353	0.079*
C12	−0.0940 (3)	0.6819 (2)	0.2785 (3)	0.0633 (8)
H12A	−0.1550	0.7164	0.3075	0.076*
C13	0.0710 (2)	0.6813 (2)	0.1768 (3)	0.0504 (6)
C14	0.1696 (3)	0.7163 (2)	0.1142 (3)	0.0581 (8)

	U11	U22	U33	U12	U13	U23
N1	0.0490 (14)	0.0711 (16)	0.0568 (14)	0.0019 (13)	0.0100 (11)	0.0026 (13)
O1	0.0755 (15)	0.0661 (14)	0.0803 (15)	0.0207 (12)	0.0173 (12)	−0.0042 (11)
C1	0.063 (2)	0.075 (2)	0.118 (3)	−0.0018 (18)	0.007 (2)	0.021 (2)
N2	0.0711 (18)	0.0628 (14)	0.0755 (17)	0.0089 (11)	0.0162 (13)	−0.0014 (12)
O2	0.0702 (15)	0.0627 (13)	0.0928 (16)	−0.0110 (11)	0.0108 (12)	0.0161 (11)
C2	0.067 (2)	0.084 (3)	0.120 (3)	−0.014 (2)	0.003 (2)	−0.005 (2)
C3	0.0509 (18)	0.101 (3)	0.076 (2)	−0.001 (2)	0.0185 (16)	0.001 (2)
C4	0.068 (2)	0.079 (3)	0.129 (3)	0.009 (2)	0.003 (2)	0.014 (2)
C5	0.073 (3)	0.072 (2)	0.113 (3)	−0.0044 (19)	0.000 (2)	−0.010 (2)
C6	0.0490 (16)	0.071 (2)	0.0572 (16)	0.0014 (16)	0.0227 (14)	0.0005 (16)
C7	0.0562 (19)	0.114 (3)	0.0586 (18)	−0.0033 (18)	0.0195 (16)	0.0010 (18)
C8	0.0532 (18)	0.0573 (19)	0.0503 (17)	0.0024 (15)	−0.0002 (13)	−0.0016 (13)
C9	0.0483 (15)	0.0511 (12)	0.0446 (15)	0.0002 (12)	0.0027 (12)	−0.0005 (12)
C10	0.0542 (17)	0.0359 (12)	0.0503 (15)	0.0001 (10)	0.0040 (12)	0.0023 (11)
C11	0.0599 (18)	0.0689 (14)	0.0665 (19)	0.0027 (14)	0.0171 (15)	0.0000 (16)
C12	0.0601 (19)	0.0673 (15)	0.0618 (18)	0.0126 (14)	0.0171 (14)	−0.0092 (16)
C13	0.0525 (15)	0.0481 (12)	0.0442 (14)	−0.0032 (12)	0.0049 (12)	0.0002 (12)
C14	0.0516 (18)	0.060 (2)	0.0516 (17)	−0.0023 (15)	−0.0014 (13)	0.0026 (14)

N1—C14	1.385 (4)	C4—H4A	0.9300
N1—C8	1.394 (3)	C5—C6	1.367 (4)
N1—C7	1.467 (4)	C5—H5A	0.9300
O1—C8	1.203 (3)	C6—C7	1.496 (4)
C1—C6	1.359 (4)	C7—H7A	0.9700
C1—C2	1.384 (5)	C7—H7B	0.9700
C1—H1A	0.9300	C8—C9	1.503 (4)
N2—C13	1.395 (3)	C9—C10	1.306 (3)
N2—C12	1.411 (4)	C9—C13	1.382 (4)
O2—C14	1.217 (3)	C10—C11	1.315 (4)
C2—C3	1.336 (4)	C10—H10A	0.9300
C2—H2B	0.9300	C11—C12	1.376 (4)
C3—C4	1.347 (4)	C11—H11A	0.9300
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.374 (4)	C13—C14	1.474 (4)
C14—N1—C8	112.4 (2)	N1—C7—H7B	109.0
C14—N1—C7	124.4 (3)	C6—C7—H7B	109.0
C8—N1—C7	123.2 (3)	H7A—C7—H7B	107.8
C6—C1—C2	121.9 (3)	O1—C8—N1	126.2 (3)
C6—C1—H1A	119.1	O1—C8—C9	128.0 (3)
C2—C1—H1A	119.1	N1—C8—C9	105.8 (2)
C13—N2—C12	113.2 (2)	C10—C9—C13	124.0 (3)
C3—C2—C1	120.5 (3)	C10—C9—C8	129.5 (3)
C3—C2—H2B	119.7	C13—C9—C8	106.5 (3)
C1—C2—H2B	119.7	C9—C10—C11	117.1 (3)
C2—C3—C4	118.7 (3)	C9—C10—H10A	121.5
C2—C3—H3A	120.7	C11—C10—H10A	121.5
C4—C3—H3A	120.7	C10—C11—C12	123.4 (3)
C3—C4—C5	121.2 (3)	C10—C11—H11A	118.3
C3—C4—H4A	119.4	C12—C11—H11A	118.3
C5—C4—H4A	119.4	C11—C12—N2	121.3 (3)
C6—C5—C4	121.2 (3)	C11—C12—H12A	119.4
C6—C5—H5A	119.4	N2—C12—H12A	119.4
C4—C5—H5A	119.4	C9—C13—N2	121.1 (3)
C1—C6—C5	116.5 (3)	C9—C13—C14	109.8 (3)
C1—C6—C7	121.8 (3)	N2—C13—C14	129.1 (2)
C5—C6—C7	121.7 (3)	O2—C14—N1	125.2 (3)
N1—C7—C6	112.7 (2)	O2—C14—C13	129.4 (3)
N1—C7—H7A	109.0	N1—C14—C13	105.4 (2)
C6—C7—H7A	109.0
C6—C1—C2—C3	2.8 (6)	C13—C9—C10—C11	0.7 (4)
C1—C2—C3—C4	−1.9 (6)	C8—C9—C10—C11	−179.4 (2)
C2—C3—C4—C5	0.6 (6)	C9—C10—C11—C12	−0.1 (4)
C3—C4—C5—C6	−0.3 (6)	C10—C11—C12—N2	−1.1 (4)
C2—C1—C6—C5	−2.4 (5)	C13—N2—C12—C11	1.4 (4)
C2—C1—C6—C7	177.4 (3)	C10—C9—C13—N2	−0.2 (4)
C4—C5—C6—C1	1.1 (5)	C8—C9—C13—N2	179.9 (2)
C4—C5—C6—C7	−178.7 (3)	C10—C9—C13—C14	178.1 (2)
C14—N1—C7—C6	91.4 (3)	C8—C9—C13—C14	−1.8 (3)
C8—N1—C7—C6	−87.6 (3)	C12—N2—C13—C9	−0.8 (4)
C1—C6—C7—N1	−88.5 (4)	C12—N2—C13—C14	−178.8 (2)
C5—C6—C7—N1	91.3 (4)	C8—N1—C14—O2	177.7 (3)
C14—N1—C8—O1	−179.2 (3)	C7—N1—C14—O2	−1.4 (4)
C7—N1—C8—O1	−0.1 (4)	C8—N1—C14—C13	−1.1 (3)
C14—N1—C8—C9	0.0 (3)	C7—N1—C14—C13	179.8 (2)
C7—N1—C8—C9	179.2 (2)	C9—C13—C14—O2	−176.9 (3)
O1—C8—C9—C10	0.5 (5)	N2—C13—C14—O2	1.2 (5)
N1—C8—C9—C10	−178.7 (3)	C9—C13—C14—N1	1.8 (3)
O1—C8—C9—C13	−179.6 (3)	N2—C13—C14—N1	179.9 (2)
N1—C8—C9—C13	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···N2i	0.93	2.46	3.386 (3)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯N2i	0.93	2.46	3.386 (3)	177

Symmetry code: (i) .