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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2710
https://doi.org/10.1107/S1600536811037901

4-(6-Chloro­imidazo[1,2-b]pyridazin-3-yl)benzo­nitrile

Yiliang Zhaoa* and Clarissa K. L. Nga

aFaculty of Pharmacy, Science Road, The University of Sydney, Sydney, Australia
*Correspondence e-mail: yiliang.zhao@sydney.edu.au

(Received 8 September 2011; accepted 16 September 2011; online 30 September 2011)

In the title compound, C13H7ClN4, 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[Kia, R., Fun, H.-K. & Kargar, H. (2009). Acta Cryst. E65, o660-o661.]); Khan et al. (2010[Khan, F. N., Manivel, P., Prabakaran, K., Hathwar, V. R. & Akkurt, M. (2010). Acta Cryst. E66, o1081.]); Xue (2010[Xue, M. W. (2010). Acta Cryst. E66, o2006.]); Zhao et al. (2009[Zhao, M. M., Li, Y. H., Wu, D. H. & Wan, Q. (2009). Acta Cryst. E65, o1261.]).

[Scheme 1]

Experimental

Crystal data

  • C13H7ClN4

  • Mr = 254.68

  • Tetragonal, I 41 /a

  • 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[Bruker (2008). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.659, Tmax = 0.746

  • 140841 measured reflections

  • 18107 independent reflections

  • 11833 reflections with I > 2σ(I)

  • Rint = 0.032
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 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

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) x, y+1, z; (ii) [-y+{\script{3\over 4}}, x+{\script{1\over 4}}, z+{\script{1\over 4}}]; (iii) [-y+{\script{3\over 4}}, x-{\script{1\over 4}}, -z+{\script{3\over 4}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811037901/ng5227sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037901/ng5227Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037901/ng5227Isup3.cml

checkCIF report


Comment top

The title compound, C13 H7 Cl1 N4, was newly synthesized, crystallized and analysed at high resolution sin theta/lambda 1.1. The bond lengths are as expected. The crystal packing reveals that in one unit cell, every four molecules stack in parallel position by a number of non-classical hydrogen bonds. Hydrogen atoms are fixed at 1.083 A as determined from neutron diffraction, and the temperature factors were refined isotropically.

Related literature top

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

Experimental top

To a thick wall borosilicate glass vial were added 6-Chloro-3-iodo-imidazo[1,2-b]pyridazine (0.05 g, 1.0 equiv.), 4-cyanophenylboronic acid (0.032 g, 1.2 equiv.), Pd(PPh3)4 (0.02 g, 10 mol%), K2CO3 (0.037 g, 1.5 equiv.), and EtOH/H2O (4 : 1, 5 ml). The vial was sealed with a silicon septum and the reaction mixture was pre-stirred for 1 min. The reaction mixture was subjected to microwave irradiation at 90 °C for 14 min at the maximum power of 300 W with sufficient stirring. The reaction mixture was cooled to room temperature and solvent was removed under reduced pressure. The crude product was purified by flash column chromatography, eluting with ethyl acetate/hexane (1 : 1) to give the titled compound as a bright yellow solid (0.038 g, 83 %).

Structure description top

The title compound, C13 H7 Cl1 N4, was newly synthesized, crystallized and analysed at high resolution sin theta/lambda 1.1. The bond lengths are as expected. The crystal packing reveals that in one unit cell, every four molecules stack in parallel position by a number of non-classical hydrogen bonds. Hydrogen atoms are fixed at 1.083 A as determined from neutron diffraction, and the temperature factors were refined isotropically.

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

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. , The ORTEP view of the title compound with 50% probability displacement elipsoids for non-H atoms.
4-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)benzonitrile top
Crystal data top
C13H7ClN4Dx = 1.500 Mg m−3
Mr = 254.68Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 500 reflections
a = 13.5513 (12) Åθ = 1.7–62.3°
c = 24.566 (3) ŵ = 0.32 mm−1
V = 4511.3 (7) Å3T = 150 K
Z = 16Block, colourless
F(000) = 20800.25 × 0.15 × 0.10 mm
none
Data collection top
Bruker SMART APEXII CCD
diffractometer		18107 independent reflections
Radiation source: fine-focus sealed tube11833 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 62.3°, θmin = 1.7°
Absorption correction: multi-scan
(SAINT; Bruker, 2008)		h = −33→32
Tmin = 0.659, Tmax = 0.746k = −33→31
140841 measured reflectionsl = −58→60
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141All 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 parametersΔρmax = 0.85 e Å−3
7 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C13H7ClN4Z = 16
Mr = 254.68Mo Kα radiation
Tetragonal, I41/aµ = 0.32 mm−1
a = 13.5513 (12) ÅT = 150 K
c = 24.566 (3) Å0.25 × 0.15 × 0.10 mm
V = 4511.3 (7) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		18107 independent reflections
Absorption correction: multi-scan
(SAINT; Bruker, 2008)		11833 reflections with I > 2σ(I)
Tmin = 0.659, Tmax = 0.746Rint = 0.032
140841 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0437 restraints
wR(F2) = 0.141All H-atom parameters refined
S = 1.08Δρmax = 0.85 e Å−3
18107 reflectionsΔρmin = −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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.39217 (3)0.36640 (3)0.159032 (17)0.01678 (5)
C20.37908 (3)0.45664 (3)0.187490 (19)0.01942 (6)
C30.36436 (3)0.45225 (3)0.242477 (19)0.01919 (6)
C40.36372 (3)0.35883 (3)0.267513 (16)0.01652 (5)
C50.35942 (3)0.23262 (3)0.319699 (16)0.01807 (5)
C60.37353 (3)0.19353 (3)0.267716 (15)0.01514 (5)
C70.37986 (3)0.09040 (3)0.251063 (15)0.01514 (5)
C80.38792 (3)0.01863 (3)0.292379 (18)0.01890 (6)
C90.38734 (4)−0.08101 (3)0.27984 (2)0.02124 (7)
C100.38037 (3)−0.11125 (3)0.22543 (2)0.01965 (6)
C110.37593 (3)−0.04085 (3)0.183904 (18)0.01980 (6)
C120.37476 (3)0.05927 (3)0.196657 (16)0.01772 (5)
C130.37580 (4)−0.21460 (3)0.21251 (2)0.02413 (8)
N10.37014 (5)−0.29780 (4)0.20267 (3)0.03142 (10)
N20.39085 (2)0.27773 (2)0.179828 (13)0.01557 (4)
N30.37627 (2)0.27594 (2)0.234420 (13)0.01445 (4)
N40.35305 (3)0.33273 (3)0.319431 (15)0.01907 (5)
Cl10.413952 (9)0.370824 (9)0.089725 (5)0.02143 (3)
H20.3846 (8)0.5243 (4)0.1643 (3)0.031 (2)*
H30.3542 (7)0.5204 (4)0.2647 (4)0.030 (2)*
H50.3569 (8)0.1898 (7)0.3569 (2)0.034 (3)*
H80.3999 (8)0.0435 (7)0.33372 (15)0.031 (2)*
H90.3914 (7)−0.1341 (6)0.3127 (3)0.029 (2)*
H110.3662 (8)−0.0628 (9)0.14188 (16)0.042 (3)*
H120.3662 (7)0.1155 (5)0.1657 (3)0.030 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.01593 (12)0.01674 (12)0.01767 (13)0.00052 (9)−0.00065 (9)0.00152 (9)
C20.02065 (14)0.01551 (12)0.02209 (15)0.00112 (10)−0.00169 (11)0.00123 (10)
C30.02072 (14)0.01484 (12)0.02199 (15)0.00197 (10)−0.00191 (11)−0.00164 (10)
C40.01706 (12)0.01544 (11)0.01706 (12)0.00196 (9)−0.00169 (9)−0.00230 (9)
C50.02051 (14)0.01867 (13)0.01504 (11)0.00221 (10)−0.00118 (10)−0.00095 (9)
C60.01548 (11)0.01474 (11)0.01520 (11)0.00104 (8)−0.00108 (8)−0.00048 (8)
C70.01486 (11)0.01468 (11)0.01587 (11)0.00048 (8)−0.00133 (8)−0.00043 (8)
C80.02312 (15)0.01589 (12)0.01768 (13)0.00058 (10)−0.00269 (11)0.00081 (10)
C90.02647 (18)0.01571 (13)0.02155 (15)0.00072 (11)−0.00397 (13)0.00104 (11)
C100.02066 (14)0.01475 (12)0.02353 (16)0.00046 (10)−0.00355 (12)−0.00161 (11)
C110.02297 (16)0.01711 (13)0.01932 (14)−0.00005 (11)−0.00236 (11)−0.00292 (10)
C120.02068 (14)0.01622 (12)0.01625 (12)−0.00001 (10)−0.00164 (10)−0.00097 (9)
C130.02702 (19)0.01604 (14)0.0293 (2)0.00087 (12)−0.00495 (16)−0.00242 (13)
N10.0399 (3)0.01696 (15)0.0374 (3)0.00031 (15)−0.0067 (2)−0.00451 (15)
N20.01569 (10)0.01588 (10)0.01514 (9)0.00048 (7)−0.00012 (7)0.00018 (7)
N30.01422 (9)0.01436 (9)0.01476 (9)0.00097 (7)−0.00081 (7)−0.00084 (7)
N40.02264 (13)0.01842 (12)0.01614 (11)0.00297 (9)−0.00162 (9)−0.00302 (9)
Cl10.02372 (5)0.02314 (5)0.01744 (4)0.00047 (3)0.00083 (3)0.00373 (3)
Geometric parameters (Å, º) top
C1—N21.3058 (5)C7—C121.4033 (5)
C1—C21.4197 (6)C7—C81.4100 (6)
C1—Cl11.7291 (5)C8—C91.3849 (6)
C2—C31.3668 (7)C8—H81.0824 (10)
C2—H21.0819 (10)C9—C101.4014 (7)
C3—C41.4074 (6)C9—H91.0824 (10)
C3—H31.0816 (10)C10—C111.3980 (7)
C4—N41.3315 (6)C10—C131.4374 (6)
C4—N31.3970 (5)C11—C121.3925 (6)
C5—N41.3593 (6)C11—H111.0825 (10)
C5—C61.3957 (5)C12—H121.0823 (10)
C5—H51.0827 (10)C13—N11.1557 (7)
C6—N31.3847 (5)N2—N31.3558 (5)
C6—C71.4588 (5)
N2—C1—C2126.74 (4)C9—C8—C7120.80 (4)
N2—C1—Cl1114.80 (3)C9—C8—H8120.9 (6)
C2—C1—Cl1118.45 (3)C7—C8—H8118.2 (6)
C3—C2—C1117.87 (4)C8—C9—C10119.84 (4)
C3—C2—H2124.6 (5)C8—C9—H9118.8 (6)
C1—C2—H2117.5 (5)C10—C9—H9121.4 (6)
C2—C3—C4118.16 (4)C11—C10—C9119.96 (4)
C2—C3—H3118.7 (5)C11—C10—C13120.14 (4)
C4—C3—H3123.2 (5)C9—C10—C13119.89 (4)
N4—C4—N3110.92 (3)C12—C11—C10120.08 (4)
N4—C4—C3131.17 (4)C12—C11—H11118.7 (7)
N3—C4—C3117.91 (4)C10—C11—H11120.9 (7)
N4—C5—C6112.52 (4)C11—C12—C7120.44 (4)
N4—C5—H5122.4 (6)C11—C12—H12121.9 (5)
C6—C5—H5125.0 (6)C7—C12—H12117.6 (5)
N3—C6—C5103.77 (3)N1—C13—C10178.50 (7)
N3—C6—C7127.26 (3)C1—N2—N3113.92 (3)
C5—C6—C7128.92 (4)N2—N3—C6127.06 (3)
C12—C7—C8118.82 (4)N2—N3—C4125.38 (3)
C12—C7—C6123.52 (3)C6—N3—C4107.54 (3)
C8—C7—C6117.62 (3)C4—N4—C5105.24 (3)
N2—C1—C2—C30.66 (7)C8—C7—C12—C111.11 (6)
Cl1—C1—C2—C3−178.41 (3)C6—C7—C12—C11−176.50 (4)
C1—C2—C3—C40.41 (6)C11—C10—C13—N1−112 (3)
C2—C3—C4—N4178.65 (4)C9—C10—C13—N167 (3)
C2—C3—C4—N3−1.24 (6)C2—C1—N2—N3−0.74 (6)
N4—C5—C6—N30.34 (5)Cl1—C1—N2—N3178.35 (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—C12166.96 (4)C5—C6—N3—N2178.38 (3)
N3—C6—C7—C8172.24 (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—C4177.58 (4)
C6—C7—C8—C9175.48 (4)N4—C4—N3—N2−178.70 (4)
C7—C8—C9—C101.11 (7)C3—C4—N3—N21.21 (6)
C8—C9—C10—C111.22 (7)N4—C4—N3—C6−0.19 (4)
C8—C9—C10—C13−177.53 (5)C3—C4—N3—C6179.72 (4)
C9—C10—C11—C12−2.37 (7)N3—C4—N4—C50.39 (5)
C13—C10—C11—C12176.38 (4)C3—C4—N4—C5−179.51 (4)
C10—C11—C12—C71.19 (7)C6—C5—N4—C4−0.46 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N1i1.08 (1)2.60 (1)3.3502 (7)126 (1)
C3—H3···Cl1ii1.08 (1)2.70 (1)3.7389 (6)161 (1)
C5—H5···N4iii1.08 (1)2.31 (1)3.3341 (7)157 (1)
C8—H8···N4iii1.08 (1)2.52 (1)3.6049 (8)177 (1)
C12—H12···N21.08 (1)2.25 (1)2.9975 (6)125 (1)
Symmetry codes: (i) x, y+1, z; (ii) −y+3/4, x+1/4, z+1/4; (iii) −y+3/4, x−1/4, −z+3/4.

Experimental details

Crystal data
Chemical formulaC13H7ClN4
Mr254.68
Crystal system, space groupTetragonal, I41/a
Temperature (K)150
a, c (Å)13.5513 (12), 24.566 (3)
V (Å3)4511.3 (7)
Z16
Radiation typeMo Kα
µ (mm−1)0.32
Crystal size (mm)0.25 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SAINT; Bruker, 2008)
Tmin, Tmax0.659, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		140841, 18107, 11833
Rint0.032
(sin θ/λ)max (Å−1)1.246
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.141, 1.08
No. of reflections18107
No. of parameters191
No. of restraints7
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.85, −0.34

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1999), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N1i1.082 (6)2.597 (6)3.3502 (7)126.1 (5)
C3—H3···Cl1ii1.081 (7)2.701 (8)3.7389 (6)160.8 (7)
C5—H5···N4iii1.082 (6)2.312 (7)3.3341 (7)156.8 (8)
C8—H8···N4iii1.082 (5)2.523 (5)3.6049 (8)176.7 (8)
C12—H12···N21.082 (7)2.246 (7)2.9975 (6)124.8 (5)
Symmetry codes: (i) x, y+1, z; (ii) −y+3/4, x+1/4, z+1/4; (iii) −y+3/4, x−1/4, −z+3/4.
 

Acknowledgements

The authors would like to thank Professor Dai Hibbs from the Faculty of Pharmacy, the University of Sydney, for his kind and generous support of this research project.

References

First citationBruker (2008). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationKhan, F. N., Manivel, P., Prabakaran, K., Hathwar, V. R. & Akkurt, M. (2010). Acta Cryst. E66, o1081.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationKia, R., Fun, H.-K. & Kargar, H. (2009). Acta Cryst. E65, o660–o661.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXue, M. W. (2010). Acta Cryst. E66, o2006.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationZhao, M. M., Li, Y. H., Wu, D. H. & Wan, Q. (2009). Acta Cryst. E65, o1261.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2710
https://doi.org/10.1107/S1600536811037901
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