N-(2-Chloro-pyrimidin-4-yl)-N,2-di-methyl-2H-indazol-6-amine.

In the title compound, C(13)H(12)ClN(5), which is a derivative of the anti-tumor agent pazopanib {systematic name: 5-[[4-[(2,3-di-methyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl]amino]-2-methylbenzolsulfonamide}, the indazole and pyrim-idine fragments form a dihedral angle of 62.63 (5)°. In the crystal, pairs of mol-ecules related by twofold rotational symmetry are linked into dimers through π-π inter-actions between the indazole ring systems [centroid-centroid distance = 3.720 (2) Å]. Weak inter-molecular C-H⋯N hydrogen bonds further assemble these dimers into columns propagated in [001].

Related literature

For background to the pharmacokinetics and clinical studies of the anti­tumor agent pazopanib, see: Limvorasak & Posadas (2009 ▶); Sloan & Scheinfeld 2008 ▶; Sonpavde et al. (2007 ▶). For the synthesis of pazopanib, see: Sorbera et al. (2006 ▶).

Experimental

Crystal data

C13H12ClN5

M = 273.73

Monoclinic,

a = 21.432 (4) Å

b = 9.836 (2) Å

c = 12.542 (3) Å

β = 90.25 (3)°

V = 2644.1 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.946, T max = 0.967

10576 measured reflections

2323 independent reflections

1982 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.01

2323 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536810042753/cv2775sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042753/cv2775Isup2.hkl

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

C13H12ClN5	F(000) = 1136
Mr = 273.73	Dx = 1.375 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.432 (4) Å	Cell parameters from 4286 reflections
b = 9.836 (2) Å	θ = 1.9–27.9°
c = 12.542 (3) Å	µ = 0.28 mm−1
β = 90.25 (3)°	T = 113 K
V = 2644.1 (9) Å3	Block, white
Z = 8	0.20 × 0.18 × 0.12 mm

Rigaku Saturn CCD area-detector diffractometer	2323 independent reflections
Radiation source: rotating anode	1982 reflections with I > 2σ(I)
confocal	Rint = 0.043
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 1.9°
ω and φ scans	h = −25→25
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −11→11
Tmin = 0.946, Tmax = 0.967	l = −14→14
10576 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2323 reflections	Δρmax = 0.21 e Å−3
175 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0191 (14)

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
Cl1	0.227613 (19)	0.06867 (4)	0.79285 (3)	0.0308 (2)
N1	0.13815 (6)	0.18363 (13)	0.68576 (10)	0.0268 (4)
N2	0.18239 (6)	0.30697 (12)	0.83256 (10)	0.0206 (3)
N3	0.14793 (6)	0.52060 (13)	0.88097 (10)	0.0206 (3)
N4	−0.06548 (6)	0.69175 (13)	0.92048 (10)	0.0223 (3)
N5	−0.08472 (6)	0.82333 (13)	0.91397 (10)	0.0218 (3)
C1	0.17633 (7)	0.20335 (15)	0.76669 (12)	0.0211 (4)
C2	0.10043 (8)	0.29266 (17)	0.66821 (13)	0.0284 (4)
H2	0.0720	0.2880	0.6101	0.034*
C3	0.10066 (8)	0.40761 (16)	0.72803 (12)	0.0235 (4)
H3	0.0736	0.4815	0.7124	0.028*
C4	0.14298 (7)	0.41252 (15)	0.81461 (12)	0.0189 (4)
C5	0.19380 (7)	0.52028 (18)	0.96815 (13)	0.0295 (4)
H5A	0.1776	0.4671	1.0280	0.044*
H5B	0.2016	0.6139	0.9915	0.044*
H5C	0.2329	0.4797	0.9432	0.044*
C6	0.10170 (7)	0.62570 (16)	0.88222 (11)	0.0194 (4)
C7	0.12160 (7)	0.76193 (16)	0.86613 (13)	0.0252 (4)
H7	0.1644	0.7801	0.8529	0.030*
C8	0.07992 (7)	0.86753 (17)	0.86940 (13)	0.0267 (4)
H8	0.0935	0.9585	0.8592	0.032*
C9	0.01641 (7)	0.83811 (15)	0.88831 (12)	0.0209 (4)
C10	−0.00297 (7)	0.70070 (15)	0.90426 (11)	0.0188 (4)
C11	0.04067 (7)	0.59365 (15)	0.90219 (12)	0.0195 (4)
H11	0.0282	0.5023	0.9142	0.023*
C12	−0.03903 (7)	0.91238 (17)	0.89500 (12)	0.0246 (4)
H12	−0.0434	1.0080	0.8875	0.030*
C13	−0.15098 (7)	0.85326 (18)	0.92276 (13)	0.0286 (4)
H13A	−0.1573	0.9519	0.9201	0.043*
H13B	−0.1667	0.8179	0.9906	0.043*
H13C	−0.1735	0.8102	0.8636	0.043*

	U11	U22	U33	U12	U13	U23
Cl1	0.0287 (3)	0.0271 (3)	0.0365 (3)	0.00976 (17)	−0.00266 (19)	−0.00407 (17)
N1	0.0329 (8)	0.0226 (8)	0.0250 (8)	0.0042 (6)	−0.0049 (6)	−0.0020 (6)
N2	0.0177 (7)	0.0222 (8)	0.0220 (7)	0.0014 (6)	0.0025 (5)	0.0001 (6)
N3	0.0176 (7)	0.0228 (7)	0.0214 (7)	0.0028 (6)	−0.0009 (5)	−0.0045 (6)
N4	0.0207 (7)	0.0194 (8)	0.0267 (8)	0.0035 (6)	0.0006 (6)	0.0018 (5)
N5	0.0223 (7)	0.0204 (7)	0.0226 (7)	0.0049 (6)	−0.0011 (5)	0.0004 (6)
C1	0.0205 (8)	0.0200 (9)	0.0228 (9)	0.0009 (7)	0.0050 (7)	0.0024 (7)
C2	0.0344 (9)	0.0284 (10)	0.0225 (9)	0.0018 (8)	−0.0080 (7)	0.0005 (7)
C3	0.0274 (9)	0.0220 (9)	0.0210 (8)	0.0041 (7)	−0.0025 (7)	0.0036 (7)
C4	0.0181 (8)	0.0203 (9)	0.0184 (8)	−0.0010 (6)	0.0052 (6)	0.0028 (6)
C5	0.0229 (9)	0.0349 (10)	0.0307 (10)	0.0057 (8)	−0.0078 (7)	−0.0107 (8)
C6	0.0206 (8)	0.0214 (9)	0.0163 (8)	0.0019 (7)	−0.0011 (6)	−0.0024 (6)
C7	0.0212 (8)	0.0254 (9)	0.0290 (9)	−0.0040 (7)	0.0022 (7)	−0.0015 (7)
C8	0.0278 (9)	0.0194 (9)	0.0328 (10)	−0.0036 (7)	0.0007 (7)	0.0011 (7)
C9	0.0239 (8)	0.0188 (8)	0.0200 (8)	−0.0002 (7)	−0.0013 (6)	0.0001 (6)
C10	0.0201 (8)	0.0199 (8)	0.0164 (8)	−0.0004 (6)	−0.0025 (6)	−0.0002 (6)
C11	0.0225 (8)	0.0176 (8)	0.0185 (8)	−0.0005 (6)	−0.0001 (6)	−0.0003 (6)
C12	0.0303 (10)	0.0180 (8)	0.0255 (9)	0.0009 (7)	−0.0013 (7)	0.0003 (7)
C13	0.0223 (9)	0.0308 (10)	0.0328 (10)	0.0082 (7)	0.0023 (7)	0.0053 (7)

Cl1—C1	1.7515 (16)	C5—H5B	0.9800
N1—C1	1.315 (2)	C5—H5C	0.9800
N1—C2	1.360 (2)	C6—C11	1.370 (2)
N2—C1	1.3182 (19)	C6—C7	1.421 (2)
N2—C4	1.3564 (19)	C7—C8	1.371 (2)
N3—C4	1.3540 (19)	C7—H7	0.9500
N3—C6	1.4321 (19)	C8—C9	1.413 (2)
N3—C5	1.467 (2)	C8—H8	0.9500
N4—C10	1.3586 (19)	C9—C12	1.398 (2)
N4—N5	1.3607 (17)	C9—C10	1.428 (2)
N5—C12	1.336 (2)	C10—C11	1.409 (2)
N5—C13	1.4551 (19)	C11—H11	0.9500
C2—C3	1.357 (2)	C12—H12	0.9500
C2—H2	0.9500	C13—H13A	0.9800
C3—C4	1.413 (2)	C13—H13B	0.9800
C3—H3	0.9500	C13—H13C	0.9800
C5—H5A	0.9800
Cg1···Cg2i	3.720 (2)
C1—N1—C2	112.08 (13)	C11—C6—C7	122.04 (14)
C1—N2—C4	115.36 (12)	C11—C6—N3	119.81 (14)
C4—N3—C6	121.42 (12)	C7—C6—N3	118.11 (13)
C4—N3—C5	120.45 (13)	C8—C7—C6	120.96 (15)
C6—N3—C5	117.04 (12)	C8—C7—H7	119.5
C10—N4—N5	103.19 (12)	C6—C7—H7	119.5
C12—N5—N4	114.34 (13)	C7—C8—C9	118.58 (15)
C12—N5—C13	126.67 (14)	C7—C8—H8	120.7
N4—N5—C13	118.92 (13)	C9—C8—H8	120.7
N1—C1—N2	131.07 (14)	C12—C9—C8	136.31 (15)
N1—C1—Cl1	114.88 (12)	C12—C9—C10	103.78 (14)
N2—C1—Cl1	114.05 (11)	C8—C9—C10	119.90 (14)
C3—C2—N1	124.52 (14)	N4—C10—C11	127.55 (14)
C3—C2—H2	117.7	N4—C10—C9	111.71 (13)
N1—C2—H2	117.7	C11—C10—C9	120.74 (14)
C2—C3—C4	117.01 (15)	C6—C11—C10	117.78 (14)
C2—C3—H3	121.5	C6—C11—H11	121.1
C4—C3—H3	121.5	C10—C11—H11	121.1
N3—C4—N2	116.87 (13)	N5—C12—C9	106.98 (14)
N3—C4—C3	123.20 (14)	N5—C12—H12	126.5
N2—C4—C3	119.91 (14)	C9—C12—H12	126.5
N3—C5—H5A	109.5	N5—C13—H13A	109.5
N3—C5—H5B	109.5	N5—C13—H13B	109.5
H5A—C5—H5B	109.5	H13A—C13—H13B	109.5
N3—C5—H5C	109.5	N5—C13—H13C	109.5
H5A—C5—H5C	109.5	H13A—C13—H13C	109.5
H5B—C5—H5C	109.5	H13B—C13—H13C	109.5
C10—N4—N5—C12	0.03 (17)	C11—C6—C7—C8	−0.4 (2)
C10—N4—N5—C13	177.21 (12)	N3—C6—C7—C8	−178.15 (13)
C2—N1—C1—N2	1.9 (2)	C6—C7—C8—C9	−0.5 (2)
C2—N1—C1—Cl1	−178.80 (12)	C7—C8—C9—C12	−178.16 (16)
C4—N2—C1—N1	−0.3 (2)	C7—C8—C9—C10	0.4 (2)
C4—N2—C1—Cl1	−179.62 (10)	N5—N4—C10—C11	−179.72 (13)
C1—N1—C2—C3	−1.4 (2)	N5—N4—C10—C9	0.32 (16)
N1—C2—C3—C4	−0.4 (3)	C12—C9—C10—N4	−0.53 (17)
C6—N3—C4—N2	−168.27 (13)	C8—C9—C10—N4	−179.54 (12)
C5—N3—C4—N2	−0.5 (2)	C12—C9—C10—C11	179.50 (13)
C6—N3—C4—C3	13.5 (2)	C8—C9—C10—C11	0.5 (2)
C5—N3—C4—C3	−178.74 (15)	C7—C6—C11—C10	1.3 (2)
C1—N2—C4—N3	179.92 (13)	N3—C6—C11—C10	179.02 (12)
C1—N2—C4—C3	−1.8 (2)	N4—C10—C11—C6	178.69 (14)
C2—C3—C4—N3	−179.73 (15)	C9—C10—C11—C6	−1.3 (2)
C2—C3—C4—N2	2.1 (2)	N4—N5—C12—C9	−0.37 (18)
C4—N3—C6—C11	57.33 (19)	C13—N5—C12—C9	−177.29 (13)
C5—N3—C6—C11	−110.80 (17)	C8—C9—C12—N5	179.28 (16)
C4—N3—C6—C7	−124.86 (16)	C10—C9—C12—N5	0.52 (16)
C5—N3—C6—C7	67.01 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···N2ii	0.98	2.56	3.517 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯N2i	0.98	2.56	3.517 (2)	166

Symmetry code: (i) .