10-Methoxy-benzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile.

In the title compound, C(16)H(10)N(4)O, both the meth-oxy and nitrile substituents lie in the plane defined by the benzo[g]imidazo[1,2-a]-1,8-naphthyridine ring system, resulting in a nearly planar geometry for the entire mol-ecule (r.m.s. deviation of the non-H atoms from the mean plane is 0.044 Å). In the solid-state, the mol-ecules form a three-dimensional polymer through inter-molecular C-H⋯N and C-H⋯O hydrogen bonds. In addition, the packing mode results in stabilizing π-π stacking inter-actions between the asymmetric units.

Related literature

For the synthesis of the title compound and a series of similar products, see: Volovnenko et al. (2009 ▶). For related compounds and their anti­bacterial or photophysical properties, see: Kondo et al. (1990 ▶); Gokhale & Seshadri (1987 ▶); Rajagopal & Seshadri (1991 ▶); Vijila et al. (2000 ▶). For the solid-state structures of other imidazonaphthyridine derivatives, see: Fun et al. (1996 ▶); Sivakumar et al. (1996a ▶,b ▶); Muthamizhchelvan et al. (2005a ▶,b ▶). For general metrical features within organic compounds, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H10N4O

M = 274.28

Monoclinic,

a = 7.710 (2) Å

b = 11.970 (2) Å

c = 13.340 (3) Å

β = 93.55 (3)°

V = 1228.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 180 K

0.40 × 0.40 × 0.35 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.95, T max = 0.97

45253 measured reflections

3532 independent reflections

2507 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.164

S = 1.08

3532 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker (2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809037544/fj2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037544/fj2229Isup2.hkl

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

C16H10N4O	F(000) = 568
Mr = 274.28	Dx = 1.483 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9999 reflections
a = 7.710 (2) Å	θ = 2.7–34.9°
b = 11.970 (2) Å	µ = 0.10 mm−1
c = 13.340 (3) Å	T = 180 K
β = 93.55 (3)°	Block, brown
V = 1228.8 (5) Å3	0.40 × 0.40 × 0.35 mm
Z = 4

Bruker APEXII diffractometer	3532 independent reflections
Radiation source: sealed tube	2507 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ scans	θmax = 29.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.95, Tmax = 0.97	k = −16→16
45253 measured reflections	l = −18→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0616P)2 + 1.0259P] where P = (Fo2 + 2Fc2)/3
3532 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.33 e Å−3
0 constraints

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
C1	0.1160 (2)	0.16186 (14)	0.60289 (12)	0.0239 (3)
C2	0.0449 (2)	0.22693 (14)	0.51977 (13)	0.0257 (3)
C3	0.0661 (2)	0.19331 (15)	0.42439 (13)	0.0264 (4)
H3	0.0201	0.2358	0.3708	0.032*
C4	0.1593 (2)	0.09249 (14)	0.40567 (12)	0.0239 (3)
C5	0.1800 (2)	0.05231 (15)	0.31021 (13)	0.0271 (4)
H5	0.1352	0.0921	0.2546	0.033*
C6	0.2686 (2)	−0.04838 (15)	0.29677 (12)	0.0262 (4)
C7	0.2865 (3)	−0.09560 (17)	0.20044 (13)	0.0339 (4)
H7	0.2407	−0.0588	0.1433	0.041*
C8	0.3705 (3)	−0.19467 (18)	0.19165 (15)	0.0378 (5)
H8	0.3800	−0.2260	0.1284	0.045*
C9	0.4435 (3)	−0.25045 (16)	0.27749 (15)	0.0344 (4)
H9	0.5029	−0.3173	0.2698	0.041*
C10	0.4285 (2)	−0.20791 (14)	0.37173 (13)	0.0268 (4)
C11	0.3374 (2)	−0.10535 (14)	0.38426 (12)	0.0232 (3)
C12	0.2307 (2)	0.02653 (14)	0.48692 (12)	0.0222 (3)
C13	0.2521 (2)	0.01703 (15)	0.67504 (13)	0.0282 (4)
H13	0.3126	−0.0494	0.6869	0.034*
C14	0.1924 (3)	0.08839 (16)	0.74444 (14)	0.0329 (4)
H14	0.2065	0.0773	0.8135	0.039*
C15	−0.0484 (2)	0.32689 (16)	0.54198 (14)	0.0307 (4)
C16	0.5661 (3)	−0.36456 (17)	0.45063 (18)	0.0399 (5)
H16A	0.4794	−0.4139	0.4207	0.060*
H16B	0.6029	−0.3913	0.5164	0.060*
H16C	0.6639	−0.3621	0.4095	0.060*
N1	0.1082 (2)	0.17940 (14)	0.69986 (11)	0.0311 (3)
N2	0.31704 (18)	−0.06777 (12)	0.47856 (10)	0.0231 (3)
N3	0.20387 (18)	0.06431 (12)	0.58360 (10)	0.0233 (3)
N4	−0.1221 (3)	0.40663 (16)	0.55947 (15)	0.0451 (5)
O1	0.49489 (18)	−0.25543 (11)	0.45838 (10)	0.0338 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0238 (8)	0.0251 (8)	0.0228 (8)	−0.0042 (6)	0.0013 (6)	0.0000 (6)
C2	0.0248 (8)	0.0261 (8)	0.0263 (8)	−0.0034 (6)	0.0010 (6)	0.0034 (6)
C3	0.0277 (8)	0.0265 (8)	0.0248 (8)	−0.0023 (6)	−0.0009 (6)	0.0060 (6)
C4	0.0253 (8)	0.0247 (8)	0.0215 (7)	−0.0043 (6)	0.0006 (6)	0.0037 (6)
C5	0.0313 (9)	0.0297 (8)	0.0201 (7)	−0.0062 (7)	−0.0001 (6)	0.0037 (6)
C6	0.0294 (8)	0.0281 (8)	0.0211 (8)	−0.0089 (7)	0.0025 (6)	−0.0002 (6)
C7	0.0440 (11)	0.0377 (10)	0.0205 (8)	−0.0124 (8)	0.0049 (7)	−0.0007 (7)
C8	0.0487 (12)	0.0401 (11)	0.0257 (9)	−0.0111 (9)	0.0107 (8)	−0.0086 (8)
C9	0.0401 (10)	0.0298 (9)	0.0344 (10)	−0.0070 (8)	0.0113 (8)	−0.0078 (7)
C10	0.0292 (8)	0.0236 (8)	0.0282 (8)	−0.0061 (6)	0.0051 (7)	−0.0006 (6)
C11	0.0249 (8)	0.0237 (8)	0.0213 (7)	−0.0074 (6)	0.0031 (6)	−0.0008 (6)
C12	0.0224 (7)	0.0242 (7)	0.0200 (7)	−0.0060 (6)	0.0011 (6)	0.0013 (6)
C13	0.0329 (9)	0.0296 (8)	0.0218 (8)	−0.0015 (7)	−0.0018 (6)	0.0046 (6)
C14	0.0385 (10)	0.0368 (10)	0.0234 (8)	−0.0033 (8)	0.0014 (7)	0.0012 (7)
C15	0.0314 (9)	0.0321 (9)	0.0285 (9)	−0.0003 (7)	0.0019 (7)	0.0026 (7)
C16	0.0434 (11)	0.0258 (9)	0.0509 (13)	0.0023 (8)	0.0056 (9)	−0.0012 (8)
N1	0.0360 (8)	0.0337 (8)	0.0239 (7)	−0.0032 (6)	0.0048 (6)	−0.0023 (6)
N2	0.0261 (7)	0.0234 (7)	0.0199 (6)	−0.0041 (5)	0.0016 (5)	0.0002 (5)
N3	0.0260 (7)	0.0237 (7)	0.0199 (6)	−0.0025 (5)	0.0000 (5)	0.0009 (5)
N4	0.0515 (11)	0.0399 (10)	0.0444 (10)	0.0086 (9)	0.0066 (8)	−0.0008 (8)
O1	0.0423 (8)	0.0264 (6)	0.0330 (7)	0.0034 (6)	0.0050 (6)	0.0004 (5)

C1—N1	1.315 (2)	C9—C10	1.368 (3)
C1—N3	1.382 (2)	C9—H9	0.9300
C1—C2	1.436 (2)	C10—O1	1.360 (2)
C2—C3	1.354 (2)	C10—C11	1.429 (2)
C2—C15	1.436 (3)	C11—N2	1.354 (2)
C3—C4	1.434 (2)	C12—N2	1.319 (2)
C3—H3	0.9300	C12—N3	1.394 (2)
C4—C5	1.380 (2)	C13—C14	1.361 (3)
C4—C12	1.424 (2)	C13—N3	1.375 (2)
C5—C6	1.402 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—N1	1.384 (3)
C6—C7	1.418 (2)	C14—H14	0.9300
C6—C11	1.425 (2)	C15—N4	1.142 (3)
C7—C8	1.360 (3)	C16—O1	1.423 (2)
C7—H7	0.9300	C16—H16A	0.9600
C8—C9	1.412 (3)	C16—H16B	0.9600
C8—H8	0.9300	C16—H16C	0.9600
N1—C1—N3	111.76 (15)	O1—C10—C11	114.95 (15)
N1—C1—C2	129.36 (16)	C9—C10—C11	119.84 (17)
N3—C1—C2	118.86 (15)	N2—C11—C6	122.89 (16)
C3—C2—C1	120.12 (16)	N2—C11—C10	118.69 (15)
C3—C2—C15	122.18 (16)	C6—C11—C10	118.41 (15)
C1—C2—C15	117.70 (16)	N2—C12—N3	117.42 (14)
C2—C3—C4	120.31 (16)	N2—C12—C4	125.71 (15)
C2—C3—H3	119.8	N3—C12—C4	116.86 (15)
C4—C3—H3	119.8	C14—C13—N3	105.12 (16)
C5—C4—C12	116.60 (16)	C14—C13—H13	127.4
C5—C4—C3	122.82 (15)	N3—C13—H13	127.4
C12—C4—C3	120.55 (15)	C13—C14—N1	111.80 (16)
C4—C5—C6	120.19 (16)	C13—C14—H14	124.1
C4—C5—H5	119.9	N1—C14—H14	124.1
C6—C5—H5	119.9	N4—C15—C2	179.7 (2)
C5—C6—C7	122.25 (17)	O1—C16—H16A	109.5
C5—C6—C11	117.77 (15)	O1—C16—H16B	109.5
C7—C6—C11	119.95 (17)	H16A—C16—H16B	109.5
C8—C7—C6	119.94 (18)	O1—C16—H16C	109.5
C8—C7—H7	120.0	H16A—C16—H16C	109.5
C6—C7—H7	120.0	H16B—C16—H16C	109.5
C7—C8—C9	120.70 (18)	C1—N1—C14	104.37 (15)
C7—C8—H8	119.6	C12—N2—C11	116.81 (14)
C9—C8—H8	119.6	C13—N3—C1	106.94 (14)
C10—C9—C8	121.13 (19)	C13—N3—C12	129.77 (15)
C10—C9—H9	119.4	C1—N3—C12	123.28 (14)
C8—C9—H9	119.4	C10—O1—C16	116.67 (15)
O1—C10—C9	125.21 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.93	2.50	3.366 (3)	156
C3—H3···N1ii	0.93	2.62	3.394 (2)	141

Cgi	Cgj	Centroid distance	Interplanar spacing i	αii	γiii
Cg1	Cg2iv	3.487 (2)	3.322	2.68	15.42
Cg2	Cg1iv	3.487 (2)	3.361	2.68	17.68
Cg3	Cg3iv	3.710 (2)	3.382	0.00	24.27
Cg1	Cg4v	3.689 (2)	3.336	5.01	25.28
Cg4	Cg1v	3.689 (2)	3.397	5.01	22.98

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.50	3.366 (3)	156
C3—H3⋯N1ii	0.93	2.62	3.394 (2)	141

Symmetry codes: (i) ; (ii) .

Table 2

π–π stacking interactions (Å, °)

Cgi	Cgj	Centroid distance	Interplanar spacing i	αii	γiii
Cg1	Cg2iv	3.487 (2)	3.322	2.68	15.42
Cg2	Cg1iv	3.487 (2)	3.361	2.68	17.68
Cg3	Cg3iv	3.710 (2)	3.382	0.00	24.27
Cg1	Cg4v	3.689 (2)	3.336	5.01	25.28
Cg4	Cg1v	3.689 (2)	3.397	5.01	22.98

Notes: (i) perpendicular distance between the centroid of the first ring and the plane of the second ring; (ii) dihedral angle between the plane of the first ring and the plane of the second ring; (iii) angle between the centroid of the first ring and the normal to the plane of the second ring; (iv) symmetry code: ; (v) symmetry code: . Cg1 is the centroid of atoms N1/C1/N2/C13/C14, Cg2 is the centroid of atoms N3/C12/C4–C6/C11, Cg3 is the centroid of atoms N2/C1–C4/C12 and Cg4 is the centroid of atoms C6–C11.