N-(2-Chloro-pyrimidin-4-yl)-2-methyl-2H-indazol-6-amine methanol monosolvate.

In the title compound, C(12)H(10)ClN(5)·CH(3)OH, the indazole ring system and the pyrimidine ring make a dihedral angle of 23.86 (4)°. In the crystal, the components are linked by N-H⋯O and O-H⋯N hydrogen bonds into chains propagated in [010]. Inter-molecular π-π inter-actions [centroid-centroid distances = 3.6404 (9), 3.6725 (9) and 3.4566 (9) Å] between the rings of neighbouring chains also stabilize the crystal packing.

Related literature

The title compound was obtained in a continuation of our studies of derivatives of the anti­tumor agent pazopanib (systematic name 5-[[4-[(2,3-dimethyl-2H-indazol-6-yl)methyl­amino]-2-pyrimidin­yl]amino]-2-methyl­benzolsulfonamide), during which we determined the crystal structure of the related compound N-(2-chloro­pyrimidin-4-yl)-N,2-dimethyl-2H-indazol-6-amine, see: Qi et al. (2010 ▶).

Experimental

Crystal data

C12H10ClN5·CH4O

M = 291.74

Monoclinic,

a = 6.9327 (8) Å

b = 17.613 (2) Å

c = 11.4883 (16) Å

β = 106.690 (8)°

V = 1343.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 113 K

0.34 × 0.28 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.909, T max = 0.966

13795 measured reflections

3193 independent reflections

2982 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 1.11

3193 reflections

191 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.22 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 I, global. DOI: 10.1107/S1600536811017831/cv5083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017831/cv5083Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811017831/cv5083Isup3.cml

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

C12H10ClN5·CH4O	F(000) = 608
Mr = 291.74	Dx = 1.442 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4513 reflections
a = 6.9327 (8) Å	θ = 1.9–27.9°
b = 17.613 (2) Å	µ = 0.29 mm−1
c = 11.4883 (16) Å	T = 113 K
β = 106.690 (8)°	Prism, colorless
V = 1343.7 (3) Å3	0.34 × 0.28 × 0.12 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3193 independent reflections
Radiation source: rotating anode	2982 reflections with I > 2σ(I)
multilayer	Rint = 0.057
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.2°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −23→23
Tmin = 0.909, Tmax = 0.966	l = −15→14
13795 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.3525P] where P = (Fo2 + 2Fc2)/3
3193 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.22 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
Cl1	−0.00948 (5)	0.910378 (17)	−0.00877 (3)	0.02682 (12)
N1	−0.00275 (16)	0.77456 (6)	−0.09446 (10)	0.0196 (2)
N2	0.16759 (15)	0.79520 (6)	0.11655 (9)	0.0171 (2)
N3	0.34415 (16)	0.69626 (6)	0.23692 (9)	0.0169 (2)
N4	0.65827 (16)	0.92220 (6)	0.46761 (9)	0.0182 (2)
N5	0.75805 (16)	0.92466 (6)	0.58823 (9)	0.0182 (2)
C1	0.05934 (19)	0.81451 (7)	0.00587 (11)	0.0183 (2)
C2	0.05172 (19)	0.70044 (7)	−0.07866 (11)	0.0196 (3)
H2	0.0110	0.6673	−0.1466	0.023*
C3	0.16207 (18)	0.67115 (7)	0.02996 (11)	0.0181 (2)
H3	0.1953	0.6187	0.0388	0.022*
C4	0.22490 (17)	0.72195 (7)	0.12872 (11)	0.0158 (2)
C5	0.45085 (18)	0.73798 (7)	0.33979 (11)	0.0163 (2)
C6	0.52216 (18)	0.69442 (7)	0.44890 (11)	0.0180 (2)
H6	0.4942	0.6416	0.4469	0.022*
C7	0.62928 (18)	0.72683 (7)	0.55577 (11)	0.0184 (2)
H7	0.6750	0.6973	0.6276	0.022*
C8	0.67065 (18)	0.80541 (7)	0.55709 (11)	0.0163 (2)
C9	0.60301 (17)	0.84828 (7)	0.44820 (11)	0.0158 (2)
C10	0.49085 (18)	0.81456 (7)	0.33800 (11)	0.0166 (2)
H10	0.4448	0.8435	0.2655	0.020*
C11	0.76954 (18)	0.85771 (7)	0.64502 (11)	0.0185 (2)
H11	0.8326	0.8478	0.7286	0.022*
C12	0.8408 (2)	0.99639 (7)	0.64371 (12)	0.0229 (3)
H12A	0.8857	0.9907	0.7323	0.034*
H12B	0.7370	1.0358	0.6215	0.034*
H12C	0.9554	1.0109	0.6147	0.034*
H3A	0.369 (2)	0.6491 (11)	0.2405 (15)	0.026 (4)*
C13	0.3829 (3)	0.48388 (8)	0.32210 (13)	0.0322 (3)
H13A	0.5208	0.4662	0.3597	0.048*
H13B	0.2942	0.4400	0.2953	0.048*
H13C	0.3367	0.5132	0.3814	0.048*
O1	0.37868 (17)	0.53015 (5)	0.22112 (9)	0.0274 (2)
H1	0.372 (3)	0.5011 (11)	0.1665 (19)	0.039 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0307 (2)	0.01501 (17)	0.02887 (19)	0.00241 (11)	−0.00087 (14)	0.00305 (11)
N1	0.0193 (5)	0.0211 (5)	0.0176 (5)	0.0000 (4)	0.0040 (4)	0.0018 (4)
N2	0.0163 (5)	0.0168 (5)	0.0171 (5)	0.0008 (4)	0.0029 (4)	0.0008 (4)
N3	0.0198 (5)	0.0133 (5)	0.0163 (5)	0.0013 (4)	0.0032 (4)	0.0005 (4)
N4	0.0197 (5)	0.0192 (5)	0.0134 (5)	0.0006 (4)	0.0008 (4)	0.0003 (4)
N5	0.0189 (5)	0.0195 (5)	0.0136 (5)	0.0005 (4)	0.0007 (4)	−0.0001 (4)
C1	0.0171 (6)	0.0160 (5)	0.0212 (6)	0.0000 (4)	0.0048 (5)	0.0021 (4)
C2	0.0195 (6)	0.0213 (6)	0.0178 (6)	−0.0015 (5)	0.0051 (5)	−0.0022 (4)
C3	0.0189 (6)	0.0170 (5)	0.0189 (6)	−0.0001 (4)	0.0059 (5)	−0.0009 (4)
C4	0.0142 (5)	0.0174 (5)	0.0169 (6)	−0.0011 (4)	0.0063 (5)	0.0009 (4)
C5	0.0156 (5)	0.0182 (6)	0.0155 (6)	0.0013 (4)	0.0050 (4)	0.0006 (4)
C6	0.0190 (6)	0.0161 (5)	0.0191 (6)	0.0005 (4)	0.0058 (5)	0.0033 (4)
C7	0.0191 (6)	0.0195 (6)	0.0167 (6)	0.0029 (4)	0.0052 (5)	0.0057 (4)
C8	0.0152 (5)	0.0200 (6)	0.0140 (5)	0.0022 (4)	0.0044 (4)	0.0028 (4)
C9	0.0146 (5)	0.0172 (5)	0.0156 (6)	0.0021 (4)	0.0042 (4)	0.0021 (4)
C10	0.0173 (6)	0.0181 (5)	0.0140 (6)	0.0015 (4)	0.0038 (4)	0.0021 (4)
C11	0.0182 (6)	0.0217 (6)	0.0149 (5)	0.0019 (4)	0.0035 (4)	0.0020 (4)
C12	0.0260 (7)	0.0199 (6)	0.0191 (6)	−0.0017 (5)	0.0004 (5)	−0.0024 (4)
C13	0.0489 (9)	0.0241 (7)	0.0239 (7)	0.0045 (6)	0.0109 (6)	0.0023 (5)
O1	0.0438 (6)	0.0168 (5)	0.0215 (5)	0.0015 (4)	0.0095 (4)	−0.0006 (4)

Cl1—C1	1.7495 (13)	C6—C7	1.3641 (18)
N1—C1	1.3130 (16)	C6—H6	0.9500
N1—C2	1.3566 (16)	C7—C8	1.4125 (17)
N2—C1	1.3219 (16)	C7—H7	0.9500
N2—C4	1.3454 (15)	C8—C11	1.3933 (17)
N3—C4	1.3576 (15)	C8—C9	1.4205 (16)
N3—C5	1.4077 (15)	C9—C10	1.4124 (17)
N3—H3A	0.846 (19)	C10—H10	0.9500
N4—C9	1.3574 (16)	C11—H11	0.9500
N4—N5	1.3601 (14)	C12—H12A	0.9800
N5—C11	1.3389 (16)	C12—H12B	0.9800
N5—C12	1.4565 (16)	C12—H12C	0.9800
C2—C3	1.3638 (17)	C13—O1	1.4111 (17)
C2—H2	0.9500	C13—H13A	0.9800
C3—C4	1.4120 (16)	C13—H13B	0.9800
C3—H3	0.9500	C13—H13C	0.9800
C5—C10	1.3783 (16)	O1—H1	0.80 (2)
C5—C6	1.4312 (16)
Cg1···Cg2i	3.6404 (9)	Cg2···Cg3iii	3.4566 (9)
Cg2···Cg3ii	3.6725 (9)
C1—N1—C2	112.94 (11)	C6—C7—H7	120.8
C1—N2—C4	114.57 (10)	C8—C7—H7	120.8
C4—N3—C5	129.02 (10)	C11—C8—C7	135.37 (11)
C4—N3—H3A	115.7 (11)	C11—C8—C9	104.85 (10)
C5—N3—H3A	114.9 (11)	C7—C8—C9	119.78 (11)
C9—N4—N5	103.58 (9)	N4—C9—C10	127.40 (11)
C11—N5—N4	114.21 (10)	N4—C9—C8	111.04 (10)
C11—N5—C12	126.14 (11)	C10—C9—C8	121.56 (11)
N4—N5—C12	119.65 (10)	C5—C10—C9	117.36 (11)
N1—C1—N2	131.22 (11)	C5—C10—H10	121.3
N1—C1—Cl1	114.91 (9)	C9—C10—H10	121.3
N2—C1—Cl1	113.87 (9)	N5—C11—C8	106.32 (11)
N1—C2—C3	123.22 (11)	N5—C11—H11	126.8
N1—C2—H2	118.4	C8—C11—H11	126.8
C3—C2—H2	118.4	N5—C12—H12A	109.5
C2—C3—C4	117.26 (11)	N5—C12—H12B	109.5
C2—C3—H3	121.4	H12A—C12—H12B	109.5
C4—C3—H3	121.4	N5—C12—H12C	109.5
N2—C4—N3	119.92 (11)	H12A—C12—H12C	109.5
N2—C4—C3	120.69 (11)	H12B—C12—H12C	109.5
N3—C4—C3	119.39 (11)	O1—C13—H13A	109.5
C10—C5—N3	123.90 (11)	O1—C13—H13B	109.5
C10—C5—C6	121.15 (11)	H13A—C13—H13B	109.5
N3—C5—C6	114.93 (10)	O1—C13—H13C	109.5
C7—C6—C5	121.72 (11)	H13A—C13—H13C	109.5
C7—C6—H6	119.1	H13B—C13—H13C	109.5
C5—C6—H6	119.1	C13—O1—H1	104.9 (14)
C6—C7—C8	118.43 (11)
C9—N4—N5—C11	0.26 (13)	C5—C6—C7—C8	−0.37 (18)
C9—N4—N5—C12	−179.77 (11)	C6—C7—C8—C11	179.08 (13)
C2—N1—C1—N2	1.7 (2)	C6—C7—C8—C9	−0.80 (17)
C2—N1—C1—Cl1	−179.22 (9)	N5—N4—C9—C10	178.57 (11)
C4—N2—C1—N1	0.2 (2)	N5—N4—C9—C8	−0.47 (13)
C4—N2—C1—Cl1	−178.82 (8)	C11—C8—C9—N4	0.50 (14)
C1—N1—C2—C3	−0.94 (18)	C7—C8—C9—N4	−179.58 (10)
N1—C2—C3—C4	−1.52 (18)	C11—C8—C9—C10	−178.60 (11)
C1—N2—C4—N3	177.11 (10)	C7—C8—C9—C10	1.31 (18)
C1—N2—C4—C3	−2.98 (16)	N3—C5—C10—C9	−178.85 (11)
C5—N3—C4—N2	−11.79 (18)	C6—C5—C10—C9	−0.61 (17)
C5—N3—C4—C3	168.30 (11)	N4—C9—C10—C5	−179.53 (11)
C2—C3—C4—N2	3.61 (17)	C8—C9—C10—C5	−0.58 (17)
C2—C3—C4—N3	−176.48 (11)	N4—N5—C11—C8	0.04 (14)
C4—N3—C5—C10	−16.33 (19)	C12—N5—C11—C8	−179.92 (12)
C4—N3—C5—C6	165.33 (11)	C7—C8—C11—N5	179.79 (13)
C10—C5—C6—C7	1.12 (18)	C9—C8—C11—N5	−0.32 (13)
N3—C5—C6—C7	179.51 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4iv	0.80 (2)	2.04 (2)	2.8394 (15)	176 (2)
N3—H3A···O1	0.846 (19)	2.110 (19)	2.9452 (14)	168.8 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N4i	0.80 (2)	2.04 (2)	2.8394 (15)	176 (2)
N3—H3A⋯O1	0.846 (19)	2.110 (19)	2.9452 (14)	168.8 (16)

Symmetry code: (i) .