4-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)benzonitrile.

In the title compound, C(13)H(7)ClN(4), the imidazopyridazine ring system is essentially planar [maximum deviation 0.015 (1) Å]. It is inclined to the benzene ring of the benzonitrile group by 11.31 (2)°. In the crystal, molecules are linked via C-H⋯Cl and C-H⋯N interactions.

Related literature

For related structures, see Kia et al. (2009 ▶); Khan et al. (2010 ▶); Xue (2010 ▶); Zhao et al. (2009 ▶).

Experimental

Crystal data

C13H7ClN4

M = 254.68

Tetragonal,

a = 13.5513 (12) Å

c = 24.566 (3) Å

V = 4511.3 (7) Å3

Z = 16

Mo Kα radiation

μ = 0.32 mm−1

T = 150 K

0.25 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.659, T max = 0.746

140841 measured reflections

18107 independent reflections

11833 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.141

S = 1.08

18107 reflections

191 parameters

7 restraints

All H-atom parameters refined

Δρmax = 0.85 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811037901/ng5227sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037901/ng5227Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037901/ng5227Isup3.cml

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

C13H7ClN4	Dx = 1.500 Mg m−3
Mr = 254.68	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 500 reflections
a = 13.5513 (12) Å	θ = 1.7–62.3°
c = 24.566 (3) Å	µ = 0.32 mm−1
V = 4511.3 (7) Å3	T = 150 K
Z = 16	Block, colourless
F(000) = 2080	0.25 × 0.15 × 0.10 mm
none

Bruker SMART APEXII CCD diffractometer	18107 independent reflections
Radiation source: fine-focus sealed tube	11833 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 62.3°, θmin = 1.7°
Absorption correction: multi-scan (SAINT; Bruker, 2008)	h = −33→32
Tmin = 0.659, Tmax = 0.746	k = −33→31
140841 measured reflections	l = −58→60

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0756P)2] where P = (Fo2 + 2Fc2)/3
18107 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.85 e Å−3
7 restraints	Δρmin = −0.34 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.Reflections -1 11 4, -2 4 0, -5 7 10, 4 4 0, 2 4 2, 1 8 13, -4 8 6, 1 3 16, -2 4 22, -1 10 1, -1 6 1, 0 0 24, -4 6 10, 4 5 11, -2 5 7 were omitted due to bad agreement statistics.

	x	y	z	Uiso*/Ueq
C1	0.39217 (3)	0.36640 (3)	0.159032 (17)	0.01678 (5)
C2	0.37908 (3)	0.45664 (3)	0.187490 (19)	0.01942 (6)
C3	0.36436 (3)	0.45225 (3)	0.242477 (19)	0.01919 (6)
C4	0.36372 (3)	0.35883 (3)	0.267513 (16)	0.01652 (5)
C5	0.35942 (3)	0.23262 (3)	0.319699 (16)	0.01807 (5)
C6	0.37353 (3)	0.19353 (3)	0.267716 (15)	0.01514 (5)
C7	0.37986 (3)	0.09040 (3)	0.251063 (15)	0.01514 (5)
C8	0.38792 (3)	0.01863 (3)	0.292379 (18)	0.01890 (6)
C9	0.38734 (4)	−0.08101 (3)	0.27984 (2)	0.02124 (7)
C10	0.38037 (3)	−0.11125 (3)	0.22543 (2)	0.01965 (6)
C11	0.37593 (3)	−0.04085 (3)	0.183904 (18)	0.01980 (6)
C12	0.37476 (3)	0.05927 (3)	0.196657 (16)	0.01772 (5)
C13	0.37580 (4)	−0.21460 (3)	0.21251 (2)	0.02413 (8)
N1	0.37014 (5)	−0.29780 (4)	0.20267 (3)	0.03142 (10)
N2	0.39085 (2)	0.27773 (2)	0.179828 (13)	0.01557 (4)
N3	0.37627 (2)	0.27594 (2)	0.234420 (13)	0.01445 (4)
N4	0.35305 (3)	0.33273 (3)	0.319431 (15)	0.01907 (5)
Cl1	0.413952 (9)	0.370824 (9)	0.089725 (5)	0.02143 (3)
H2	0.3846 (8)	0.5243 (4)	0.1643 (3)	0.031 (2)*
H3	0.3542 (7)	0.5204 (4)	0.2647 (4)	0.030 (2)*
H5	0.3569 (8)	0.1898 (7)	0.3569 (2)	0.034 (3)*
H8	0.3999 (8)	0.0435 (7)	0.33372 (15)	0.031 (2)*
H9	0.3914 (7)	−0.1341 (6)	0.3127 (3)	0.029 (2)*
H11	0.3662 (8)	−0.0628 (9)	0.14188 (16)	0.042 (3)*
H12	0.3662 (7)	0.1155 (5)	0.1657 (3)	0.030 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.01593 (12)	0.01674 (12)	0.01767 (13)	0.00052 (9)	−0.00065 (9)	0.00152 (9)
C2	0.02065 (14)	0.01551 (12)	0.02209 (15)	0.00112 (10)	−0.00169 (11)	0.00123 (10)
C3	0.02072 (14)	0.01484 (12)	0.02199 (15)	0.00197 (10)	−0.00191 (11)	−0.00164 (10)
C4	0.01706 (12)	0.01544 (11)	0.01706 (12)	0.00196 (9)	−0.00169 (9)	−0.00230 (9)
C5	0.02051 (14)	0.01867 (13)	0.01504 (11)	0.00221 (10)	−0.00118 (10)	−0.00095 (9)
C6	0.01548 (11)	0.01474 (11)	0.01520 (11)	0.00104 (8)	−0.00108 (8)	−0.00048 (8)
C7	0.01486 (11)	0.01468 (11)	0.01587 (11)	0.00048 (8)	−0.00133 (8)	−0.00043 (8)
C8	0.02312 (15)	0.01589 (12)	0.01768 (13)	0.00058 (10)	−0.00269 (11)	0.00081 (10)
C9	0.02647 (18)	0.01571 (13)	0.02155 (15)	0.00072 (11)	−0.00397 (13)	0.00104 (11)
C10	0.02066 (14)	0.01475 (12)	0.02353 (16)	0.00046 (10)	−0.00355 (12)	−0.00161 (11)
C11	0.02297 (16)	0.01711 (13)	0.01932 (14)	−0.00005 (11)	−0.00236 (11)	−0.00292 (10)
C12	0.02068 (14)	0.01622 (12)	0.01625 (12)	−0.00001 (10)	−0.00164 (10)	−0.00097 (9)
C13	0.02702 (19)	0.01604 (14)	0.0293 (2)	0.00087 (12)	−0.00495 (16)	−0.00242 (13)
N1	0.0399 (3)	0.01696 (15)	0.0374 (3)	0.00031 (15)	−0.0067 (2)	−0.00451 (15)
N2	0.01569 (10)	0.01588 (10)	0.01514 (9)	0.00048 (7)	−0.00012 (7)	0.00018 (7)
N3	0.01422 (9)	0.01436 (9)	0.01476 (9)	0.00097 (7)	−0.00081 (7)	−0.00084 (7)
N4	0.02264 (13)	0.01842 (12)	0.01614 (11)	0.00297 (9)	−0.00162 (9)	−0.00302 (9)
Cl1	0.02372 (5)	0.02314 (5)	0.01744 (4)	0.00047 (3)	0.00083 (3)	0.00373 (3)

C1—N2	1.3058 (5)	C7—C12	1.4033 (5)
C1—C2	1.4197 (6)	C7—C8	1.4100 (6)
C1—Cl1	1.7291 (5)	C8—C9	1.3849 (6)
C2—C3	1.3668 (7)	C8—H8	1.0824 (10)
C2—H2	1.0819 (10)	C9—C10	1.4014 (7)
C3—C4	1.4074 (6)	C9—H9	1.0824 (10)
C3—H3	1.0816 (10)	C10—C11	1.3980 (7)
C4—N4	1.3315 (6)	C10—C13	1.4374 (6)
C4—N3	1.3970 (5)	C11—C12	1.3925 (6)
C5—N4	1.3593 (6)	C11—H11	1.0825 (10)
C5—C6	1.3957 (5)	C12—H12	1.0823 (10)
C5—H5	1.0827 (10)	C13—N1	1.1557 (7)
C6—N3	1.3847 (5)	N2—N3	1.3558 (5)
C6—C7	1.4588 (5)
N2—C1—C2	126.74 (4)	C9—C8—C7	120.80 (4)
N2—C1—Cl1	114.80 (3)	C9—C8—H8	120.9 (6)
C2—C1—Cl1	118.45 (3)	C7—C8—H8	118.2 (6)
C3—C2—C1	117.87 (4)	C8—C9—C10	119.84 (4)
C3—C2—H2	124.6 (5)	C8—C9—H9	118.8 (6)
C1—C2—H2	117.5 (5)	C10—C9—H9	121.4 (6)
C2—C3—C4	118.16 (4)	C11—C10—C9	119.96 (4)
C2—C3—H3	118.7 (5)	C11—C10—C13	120.14 (4)
C4—C3—H3	123.2 (5)	C9—C10—C13	119.89 (4)
N4—C4—N3	110.92 (3)	C12—C11—C10	120.08 (4)
N4—C4—C3	131.17 (4)	C12—C11—H11	118.7 (7)
N3—C4—C3	117.91 (4)	C10—C11—H11	120.9 (7)
N4—C5—C6	112.52 (4)	C11—C12—C7	120.44 (4)
N4—C5—H5	122.4 (6)	C11—C12—H12	121.9 (5)
C6—C5—H5	125.0 (6)	C7—C12—H12	117.6 (5)
N3—C6—C5	103.77 (3)	N1—C13—C10	178.50 (7)
N3—C6—C7	127.26 (3)	C1—N2—N3	113.92 (3)
C5—C6—C7	128.92 (4)	N2—N3—C6	127.06 (3)
C12—C7—C8	118.82 (4)	N2—N3—C4	125.38 (3)
C12—C7—C6	123.52 (3)	C6—N3—C4	107.54 (3)
C8—C7—C6	117.62 (3)	C4—N4—C5	105.24 (3)
N2—C1—C2—C3	0.66 (7)	C8—C7—C12—C11	1.11 (6)
Cl1—C1—C2—C3	−178.41 (3)	C6—C7—C12—C11	−176.50 (4)
C1—C2—C3—C4	0.41 (6)	C11—C10—C13—N1	−112 (3)
C2—C3—C4—N4	178.65 (4)	C9—C10—C13—N1	67 (3)
C2—C3—C4—N3	−1.24 (6)	C2—C1—N2—N3	−0.74 (6)
N4—C5—C6—N3	0.34 (5)	Cl1—C1—N2—N3	178.35 (3)
N4—C5—C6—C7	−177.28 (4)	C1—N2—N3—C6	−178.44 (4)
N3—C6—C7—C12	−10.13 (6)	C1—N2—N3—C4	−0.23 (5)
C5—C6—C7—C12	166.96 (4)	C5—C6—N3—N2	178.38 (3)
N3—C6—C7—C8	172.24 (4)	C7—C6—N3—N2	−3.94 (6)
C5—C6—C7—C8	−10.67 (6)	C5—C6—N3—C4	−0.09 (4)
C12—C7—C8—C9	−2.26 (6)	C7—C6—N3—C4	177.58 (4)
C6—C7—C8—C9	175.48 (4)	N4—C4—N3—N2	−178.70 (4)
C7—C8—C9—C10	1.11 (7)	C3—C4—N3—N2	1.21 (6)
C8—C9—C10—C11	1.22 (7)	N4—C4—N3—C6	−0.19 (4)
C8—C9—C10—C13	−177.53 (5)	C3—C4—N3—C6	179.72 (4)
C9—C10—C11—C12	−2.37 (7)	N3—C4—N4—C5	0.39 (5)
C13—C10—C11—C12	176.38 (4)	C3—C4—N4—C5	−179.51 (4)
C10—C11—C12—C7	1.19 (7)	C6—C5—N4—C4	−0.46 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1i	1.08 (1)	2.60 (1)	3.3502 (7)	126.(1)
C3—H3···Cl1ii	1.08 (1)	2.70 (1)	3.7389 (6)	161.(1)
C5—H5···N4iii	1.08 (1)	2.31 (1)	3.3341 (7)	157.(1)
C8—H8···N4iii	1.08 (1)	2.52 (1)	3.6049 (8)	177.(1)
C12—H12···N2	1.08 (1)	2.25 (1)	2.9975 (6)	125.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1i	1.08 (1)	2.60 (1)	3.3502 (7)	126 (1)
C3—H3⋯Cl1ii	1.08 (1)	2.70 (1)	3.7389 (6)	161 (1)
C5—H5⋯N4iii	1.08 (1)	2.31 (1)	3.3341 (7)	157 (1)
C8—H8⋯N4iii	1.08 (1)	2.52 (1)	3.6049 (8)	177 (1)
C12—H12⋯N2	1.08 (1)	2.25 (1)	2.9975 (6)	125 (1)

Symmetry codes: (i) ; (ii) ; (iii) .