10-Methoxy­benzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile

Tarasov, A.V.; Volovnenko, T.A.; Lugan, N.; Volovenko, Y.M.

doi:10.1107/S1600536809037544

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2524-o2525

doi:10.1107/S1600536809037544

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10-Methoxybenzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile

Andrii V. Tarasov,^a ^* Tatyana A. Volovnenko,^a Noël Lugan ^b and Yulian M. Volovenko ^a

^aDepartment of Chemistry, National Taras Shevchenko University, 64 Volodymyrska St, Kyiv 01601, Ukraine, and ^bLaboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, 31077 Toulouse CEDEX 4, France
^*Correspondence e-mail: antaran@gala.net

(Received 17 June 2009; accepted 16 September 2009; online 26 September 2009)

In the title compound, C₁₆H₁₀N₄O, both the methoxy 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 molecule (r.m.s. deviation of the non-H atoms from the mean plane is 0.044 Å). In the solid-state, the molecules form a three-dimensional polymer through intermolecular C—H⋯N and C—H⋯O hydrogen bonds. In addition, the packing mode results in stabilizing π–π stacking interactions 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_r = 274.28
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.164
S = 1.08
3532 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
π–π stacking interactions (Å, °)

Cg_i	Cg_j	Centroid distance	Interplanar spacing ⁱ	αⁱⁱ	γⁱⁱⁱ
Cg1	Cg2^iv	3.487 (2)	3.322	2.68	15.42
Cg2	Cg1^iv	3.487 (2)	3.361	2.68	17.68
Cg3	Cg3^iv	3.710 (2)	3.382	0.00	24.27
Cg1	Cg4^v	3.689 (2)	3.336	5.01	25.28
Cg4	Cg1^v	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: -x, -y, 1-z; (v) symmetry code: 1 - x, -y,1 - z. 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.

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 ).

Supporting information

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

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

checkCIF report

Comment top

New heterocyclic nitrogen-containing systems are always of great interest to synthetic as well as pharmaceutical organic chemists. We have recently reported an efficient and versatile route to benzo[g]imidazo[1,2-a]-1,8-naphthyridines upon thermal reaction of 2-chloroquinoline-3-carbaldehydes with 1-substitued hetarylacetonitriles (Volovnenko et al., 2009). Here we report the crystal structure of the one of synthesized compound, namely, 10-methoxybenzo[g]imidazo[1,2-a]-1,8-naphthyridine-4-carbonitrile. It has been reported that products with similar structures possess not only antibacterial activity (Kondo et al., 1990) but also interesting photophysical properties (Gokhale & Seshadri, 1987; Rajagopal & Seshadri, 1991; Vijila et al., 2000).

Fig. 1 shows a perspective view of the asymetric unit of the title compound, including the labelling scheme. Selected bond distances and angles are given in Table 1. The benzo[g]imidazo[1,2-a]-1,8-naphthyridine core is almost planar (RMS deviation of C1>C14 and N1>N3 from mean plane is 0.035 Å). In addition, both methoxy and carbonitrile substituents attached to C(2) and C(11), respectively, are oriented in such a way that they both lay in heterocyle plane granting a nearly planar geometry to the entire molecule (RMS deviation of the all non-hydrogen atoms from mean plane is 0.044 Å). Bond distances and angles in the title compound are normal (Allen et al., 1987) and compare well with other imidazonaphtyridines derivatives (Fun et al., 1996; Sivakumar et al..1996a,b; Muthamizhchelvan et al., 2005a,b).

The crystal structure is stabilized by C—H···N and C—H···O intermolecular hydrogen bonds (Table 1) forming a three dimensional polymeric structure (Figure 2). In addition, the asymmetric units are seen to be stacked along the (100) axis with relatively short interplanar distances (Table 3) possibly allowing additional stabilization through π–π stacking interactions (Figure 3).

Related literature top

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 top

The title compound was synthesized by the reaction of 2-chloro-8-methoxyquinoline-3-carbaldehyde (2 mmol) with (1-benzyl-1H-imidazol-2-yl)acetonitrile (2 mmol) in dimethylformamide (3 ml). After refluxing for 1 h, the reaction mixture was left to stand overnight. The resulting crude solid was filtered, washed twice with acetone (10 ml) and dried. Yield: 96%. Crystals suitable for X-ray analysis were obtained by slow crystallization from hot dimethylformamide.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: sAINT (Bruker (2007); data reduction: SAINT (Bruker (2007); 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).

Figures top

	Fig. 1. A perspective view of the title compound, with 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram for the title compound, evidencing C—H···N et C—H···O hydrogen bonds (blue dotted lines).
	Fig. 3. A packing diagram for the title compound, evidencing π-π stacking interactions (red dotted lines).

10-Methoxybenzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile top

Crystal data top

C₁₆H₁₀N₄O	F(000) = 568
M_r = 274.28	D_x = 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

Data collection top

Bruker APEXII diffractometer	3532 independent reflections
Radiation source: sealed tube	2507 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ scans	θ_max = 29.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
T_min = 0.95, T_max = 0.97	k = −16→16
45253 measured reflections	l = −18→18

Refinement top

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(F_o²) + (0.0616P)² + 1.0259P] where P = (F_o² + 2F_c²)/3
3532 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³
0 constraints

Crystal data top

C₁₆H₁₀N₄O	V = 1228.8 (5) Å³
M_r = 274.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.710 (2) Å	µ = 0.10 mm⁻¹
b = 11.970 (2) Å	T = 180 K
c = 13.340 (3) Å	0.40 × 0.40 × 0.35 mm
β = 93.55 (3)°

Data collection top

Bruker APEXII diffractometer	3532 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2507 reflections with I > 2σ(I)
T_min = 0.95, T_max = 0.97	R_int = 0.050
45253 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.08	Δρ_max = 0.33 e Å⁻³
3532 reflections	Δρ_min = −0.34 e Å⁻³
191 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y−1/2, z−1/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀N₄O
M_r	274.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	180
a, b, c (Å)	7.710 (2), 11.970 (2), 13.340 (3)
β (°)	93.55 (3)
V (Å³)	1228.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.40 × 0.35

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.95, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	45253, 3532, 2507
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.700

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.164, 1.08
No. of reflections	3532
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.34

Computer programs: APEX2 (Bruker, 2007), sAINT (Bruker (2007), SAINT (Bruker (2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1999) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.9300	2.5000	3.366 (3)	156.00
C3—H3···N1ⁱⁱ	0.9300	2.6200	3.394 (2)	141.00

Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, −y+1/2, z−1/2.

π–π stacking interactions (Å, °) top

Cg_i	Cg_j	Centroid distance	Interplanar spacing ⁱ	αⁱⁱ	γⁱⁱⁱ
Cg1	Cg2^iv	3.487 (2)	3.322	2.68	15.42
Cg2	Cg1^iv	3.487 (2)	3.361	2.68	17.68
Cg3	Cg3^iv	3.710 (2)	3.382	0.00	24.27
Cg1	Cg4^v	3.689 (2)	3.336	5.01	25.28
Cg4	Cg1^v	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: -x, -y, 1-z; (v) symmetry code: 1 - x, -y,1 - z. 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.

Acknowledgements

This research was performed within the framework of the GDRI `Franco–Ukrainian association of Molecular Chemistry'.

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