1,2,3,6,7,8-Hexahydro-cinnolino[5,4,3-cde]cinnoline.

The title compound, C(12)H(12)N(4), was synthesized by the reaction of hydrazine hydrate and 9-methyl-3,4,6,7-tetra-hydro-2H-xanthene-1,8(5H,9H)-dione in ethanol. In the crystal, the mol-ecule lies across an inversion centre. The pyridazine rings are coplanar and the C(6) rings adopt envelope conformations.

Related literature

For the biological properties of cinnoline and its derivatives, see: Abdelrazek et al. (2006 ▶); Gomtsyan et al. (2005 ▶); Inoue et al. (1993 ▶); Lewgowd & Stanczak (2007 ▶); Lewgowd et al. (2005 ▶); Singh et al. (2003 ▶); Stefanska et al. (2003 ▶); Tutsumi et al. (1992 ▶).

Experimental

Crystal data

C12H12N4

M = 212.26

Monoclinic,

a = 9.698 (5) Å

b = 5.875 (3) Å

c = 10.023 (5) Å

β = 117.314 (6)°

V = 507.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.55 × 0.41 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.953, T max = 0.992

2508 measured reflections

890 independent reflections

575 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.123

S = 1.01

890 reflections

97 parameters

All H-atom parameters refined

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808044036/ci2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808044036/ci2750Isup2.hkl

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

C12H12N4	F(000) = 224
Mr = 212.26	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Melting point = 543–544 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.698 (5) Å	Cell parameters from 734 reflections
b = 5.875 (3) Å	θ = 2.4–26.3°
c = 10.023 (5) Å	µ = 0.09 mm−1
β = 117.314 (6)°	T = 298 K
V = 507.4 (4) Å3	Plate, colourless
Z = 2	0.55 × 0.41 × 0.09 mm

Bruker SMART CCD area-detector diffractometer	890 independent reflections
Radiation source: fine-focus sealed tube	575 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 4.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.953, Tmax = 0.992	k = −6→6
2508 measured reflections	l = −11→11

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	All H-atom parameters refined
S = 1.01	w = 1/[σ2(Fo2) + (0.0655P)2 + 0.0552P] where P = (Fo2 + 2Fc2)/3
890 reflections	(Δ/σ)max = 0.001
97 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.15 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	0.7159 (2)	−0.2597 (3)	0.65617 (19)	0.0547 (6)
N2	0.5861 (2)	−0.3398 (3)	0.66438 (18)	0.0555 (6)
C1	0.7050 (2)	−0.0820 (4)	0.5729 (2)	0.0466 (6)
C2	0.56377 (19)	0.0384 (3)	0.49395 (18)	0.0390 (5)
C3	0.5474 (2)	0.2352 (3)	0.4062 (2)	0.0450 (5)
C4	0.6864 (3)	0.3211 (5)	0.3949 (3)	0.0581 (7)
C5	0.8354 (3)	0.2567 (4)	0.5326 (3)	0.0647 (7)
C6	0.8445 (3)	0.0004 (4)	0.5597 (3)	0.0621 (7)
H1	0.682 (2)	0.250 (4)	0.305 (3)	0.065 (6)*
H2	0.678 (2)	0.487 (4)	0.382 (2)	0.076 (7)*
H3	0.930 (3)	0.308 (4)	0.522 (3)	0.086 (8)*
H4	0.839 (3)	0.340 (4)	0.623 (3)	0.079 (7)*
H5	0.846 (2)	−0.086 (4)	0.470 (2)	0.072 (7)*
H6	0.936 (3)	−0.039 (4)	0.649 (3)	0.081 (7)*

	U11	U22	U33	U12	U13	U23
N1	0.0567 (12)	0.0508 (12)	0.0500 (10)	0.0164 (9)	0.0187 (9)	0.0061 (8)
N2	0.0652 (12)	0.0458 (11)	0.0474 (11)	0.0115 (9)	0.0189 (9)	0.0086 (8)
C1	0.0501 (12)	0.0467 (12)	0.0395 (10)	0.0102 (10)	0.0175 (9)	−0.0019 (10)
C2	0.0445 (11)	0.0386 (11)	0.0306 (9)	0.0072 (8)	0.0146 (8)	−0.0029 (8)
C3	0.0574 (13)	0.0386 (12)	0.0351 (10)	0.0051 (10)	0.0178 (9)	−0.0010 (9)
C4	0.0737 (17)	0.0505 (15)	0.0555 (14)	−0.0061 (12)	0.0344 (13)	−0.0027 (12)
C5	0.0595 (15)	0.0680 (17)	0.0681 (16)	−0.0087 (13)	0.0306 (13)	−0.0101 (13)
C6	0.0484 (14)	0.0707 (18)	0.0650 (16)	0.0111 (11)	0.0242 (13)	−0.0033 (12)

N1—C1	1.310 (3)	C4—C5	1.518 (3)
N1—N2	1.381 (2)	C4—H1	0.98 (2)
N2—C3i	1.309 (3)	C4—H2	0.98 (2)
C1—C2	1.417 (3)	C5—C6	1.526 (3)
C1—C6	1.499 (3)	C5—H3	1.01 (2)
C2—C2i	1.373 (3)	C5—H4	1.01 (2)
C2—C3	1.417 (3)	C6—H5	1.04 (2)
C3—N2i	1.309 (3)	C6—H6	0.95 (2)
C3—C4	1.492 (3)
C1—N1—N2	120.01 (17)	C5—C4—H2	111.0 (13)
C3i—N2—N1	120.67 (18)	H1—C4—H2	109.4 (18)
N1—C1—C2	121.89 (19)	C4—C5—C6	111.2 (2)
N1—C1—C6	120.07 (18)	C4—C5—H3	111.1 (13)
C2—C1—C6	118.0 (2)	C6—C5—H3	109.2 (14)
C2i—C2—C3	118.3 (2)	C4—C5—H4	108.6 (14)
C2i—C2—C1	117.8 (2)	C6—C5—H4	110.1 (13)
C3—C2—C1	123.94 (17)	H3—C5—H4	106.5 (19)
N2i—C3—C2	121.33 (19)	C1—C6—C5	110.70 (19)
N2i—C3—C4	120.3 (2)	C1—C6—H5	107.1 (12)
C2—C3—C4	118.39 (18)	C5—C6—H5	110.5 (12)
C3—C4—C5	111.3 (2)	C1—C6—H6	109.2 (14)
C3—C4—H1	105.8 (12)	C5—C6—H6	111.1 (15)
C5—C4—H1	110.6 (12)	H5—C6—H6	108.2 (19)
C3—C4—H2	108.6 (13)