4-(But-3-yn-yloxy)-6-(4-iodo-1H-pyrazol-1-yl)pyrimidine.

In the title compound, C(11)H(9)IN(4)O, the dihedral angle between the pyrazole and pyrimidine rings is 6.30 (16)°. In the crystal, weak C-H⋯O inter-actions link the mol-ecules.

Related literature

For pharmacological background, see: Ma et al. (2009 ▶); Shiga et al. (2003 ▶).

Experimental

Crystal data

C11H9IN4O

M = 340.12

Monoclinic,

a = 19.511 (4) Å

b = 4.2670 (9) Å

c = 15.129 (3) Å

β = 109.18 (3)°

V = 1189.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.68 mm−1

T = 173 K

0.16 × 0.15 × 0.14 mm

Data collection

Rigaku MM007HF + CCD (Saturn724+) diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.674, T max = 0.705

8082 measured reflections

2713 independent reflections

2577 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.069

S = 1.11

2713 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.68 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044031/hb5171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044031/hb5171Isup2.hkl

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

C11H9IN4O	F(000) = 656
Mr = 340.12	Dx = 1.899 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3485 reflections
a = 19.511 (4) Å	θ = 2.2–27.5°
b = 4.2670 (9) Å	µ = 2.68 mm−1
c = 15.129 (3) Å	T = 173 K
β = 109.18 (3)°	Block, colourless
V = 1189.6 (4) Å3	0.16 × 0.15 × 0.14 mm
Z = 4

Rigaku MM007HF + CCD (Saturn724+) diffractometer	2713 independent reflections
Radiation source: Rotating Anode	2577 reflections with I > 2σ(I)
Confocal	Rint = 0.038
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 2.2°
ω scans at fixed χ = 45°	h = −17→25
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −3→5
Tmin = 0.674, Tmax = 0.705	l = −19→19
8082 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0244P)2 + 1.6155P] where P = (Fo2 + 2Fc2)/3
2713 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.68 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
I1	0.073003 (10)	0.85153 (4)	0.354299 (12)	0.02946 (8)
O1	0.28021 (11)	−0.1265 (5)	0.89982 (14)	0.0257 (4)
N1	0.12131 (13)	0.5308 (7)	0.63643 (17)	0.0292 (5)
N2	0.17939 (12)	0.4249 (6)	0.61341 (15)	0.0217 (5)
N3	0.29051 (13)	0.1759 (6)	0.65001 (17)	0.0281 (5)
N4	0.34178 (13)	−0.1049 (6)	0.79327 (17)	0.0258 (5)
C1	0.11287 (15)	0.6716 (6)	0.48870 (19)	0.0236 (6)
C2	0.08146 (17)	0.6802 (7)	0.5602 (2)	0.0304 (7)
H2	0.0368	0.7814	0.5544	0.037*
C3	0.17555 (14)	0.5053 (7)	0.52485 (18)	0.0232 (5)
H3	0.2097	0.4556	0.4944	0.028*
C4	0.23353 (14)	0.2441 (7)	0.67752 (18)	0.0202 (5)
C5	0.34119 (16)	0.0049 (8)	0.7106 (2)	0.0323 (7)
H5	0.3823	−0.0458	0.6929	0.039*
C6	0.28450 (14)	−0.0285 (7)	0.81731 (18)	0.0218 (5)
C7	0.22707 (15)	0.1515 (6)	0.7616 (2)	0.0213 (5)
H7	0.1866	0.2062	0.7801	0.026*
C8	0.33899 (15)	−0.3164 (7)	0.9591 (2)	0.0254 (6)
H8A	0.3574	−0.4565	0.9198	0.030*
H8B	0.3209	−0.4486	1.0004	0.030*
C9	0.40039 (15)	−0.1086 (7)	1.0183 (2)	0.0266 (6)
H9A	0.4196	0.0174	0.9768	0.032*
H9B	0.3813	0.0378	1.0554	0.032*
C10	0.45916 (15)	−0.2943 (7)	1.0816 (2)	0.0255 (6)
C11	0.50610 (16)	−0.4493 (8)	1.1313 (2)	0.0322 (6)
H11	0.5439	−0.5741	1.1714	0.039*

	U11	U22	U33	U12	U13	U23
I1	0.03776 (13)	0.02646 (12)	0.01837 (11)	0.00202 (7)	0.00135 (8)	0.00445 (7)
O1	0.0241 (10)	0.0348 (11)	0.0192 (9)	0.0074 (8)	0.0083 (8)	0.0097 (8)
N1	0.0288 (12)	0.0389 (14)	0.0208 (12)	0.0103 (11)	0.0094 (9)	0.0032 (11)
N2	0.0217 (11)	0.0264 (11)	0.0155 (10)	0.0027 (9)	0.0039 (8)	0.0010 (9)
N3	0.0245 (12)	0.0402 (15)	0.0200 (12)	0.0071 (10)	0.0079 (10)	0.0063 (10)
N4	0.0227 (11)	0.0348 (13)	0.0193 (11)	0.0067 (9)	0.0061 (9)	0.0024 (10)
C1	0.0281 (14)	0.0230 (14)	0.0167 (13)	0.0016 (10)	0.0035 (11)	0.0009 (10)
C2	0.0287 (15)	0.0376 (17)	0.0235 (15)	0.0106 (12)	0.0063 (12)	0.0030 (12)
C3	0.0251 (13)	0.0276 (14)	0.0149 (12)	0.0001 (11)	0.0039 (10)	0.0035 (10)
C4	0.0204 (12)	0.0207 (12)	0.0167 (12)	−0.0006 (10)	0.0025 (9)	−0.0013 (10)
C5	0.0265 (14)	0.048 (2)	0.0252 (14)	0.0129 (13)	0.0124 (11)	0.0054 (13)
C6	0.0225 (12)	0.0248 (13)	0.0160 (12)	−0.0009 (10)	0.0037 (10)	0.0009 (10)
C7	0.0199 (12)	0.0253 (14)	0.0186 (13)	0.0031 (9)	0.0064 (10)	0.0015 (10)
C8	0.0262 (14)	0.0263 (14)	0.0208 (13)	0.0046 (11)	0.0041 (11)	0.0091 (11)
C9	0.0270 (14)	0.0268 (14)	0.0232 (14)	0.0032 (11)	0.0042 (11)	0.0041 (11)
C10	0.0251 (14)	0.0294 (14)	0.0221 (13)	−0.0019 (11)	0.0076 (11)	0.0010 (11)
C11	0.0270 (15)	0.0389 (17)	0.0289 (15)	0.0044 (13)	0.0066 (12)	0.0056 (14)

I1—C1	2.071 (3)	C3—H3	0.9500
O1—C6	1.345 (3)	C4—C7	1.376 (4)
O1—C8	1.449 (3)	C5—H5	0.9500
N1—C2	1.324 (4)	C6—C7	1.391 (4)
N1—N2	1.367 (3)	C7—H7	0.9500
N2—C3	1.361 (3)	C8—C9	1.523 (4)
N2—C4	1.406 (3)	C8—H8A	0.9900
N3—C5	1.325 (4)	C8—H8B	0.9900
N3—C4	1.341 (3)	C9—C10	1.462 (4)
N4—C6	1.325 (3)	C9—H9A	0.9900
N4—C5	1.332 (4)	C9—H9B	0.9900
C1—C3	1.363 (4)	C10—C11	1.178 (4)
C1—C2	1.408 (4)	C11—H11	0.9500
C2—H2	0.9500
C6—O1—C8	118.1 (2)	N4—C5—H5	115.9
C2—N1—N2	103.7 (2)	N4—C6—O1	119.6 (2)
C3—N2—N1	112.7 (2)	N4—C6—C7	123.6 (2)
C3—N2—C4	127.1 (2)	O1—C6—C7	116.8 (2)
N1—N2—C4	120.2 (2)	C4—C7—C6	114.7 (2)
C5—N3—C4	114.3 (2)	C4—C7—H7	122.6
C6—N4—C5	115.0 (2)	C6—C7—H7	122.6
C3—C1—C2	105.4 (2)	O1—C8—C9	110.4 (2)
C3—C1—I1	125.8 (2)	O1—C8—H8A	109.6
C2—C1—I1	128.8 (2)	C9—C8—H8A	109.6
N1—C2—C1	112.2 (3)	O1—C8—H8B	109.6
N1—C2—H2	123.9	C9—C8—H8B	109.6
C1—C2—H2	123.9	H8A—C8—H8B	108.1
N2—C3—C1	106.2 (2)	C10—C9—C8	111.5 (2)
N2—C3—H3	126.9	C10—C9—H9A	109.3
C1—C3—H3	126.9	C8—C9—H9A	109.3
N3—C4—C7	124.2 (2)	C10—C9—H9B	109.3
N3—C4—N2	114.6 (2)	C8—C9—H9B	109.3
C7—C4—N2	121.2 (2)	H9A—C9—H9B	108.0
N3—C5—N4	128.2 (3)	C11—C10—C9	178.6 (4)
N3—C5—H5	115.9	C10—C11—H11	180.0
C2—N1—N2—C3	−0.3 (3)	N1—N2—C4—C7	4.6 (4)
C2—N1—N2—C4	−178.2 (3)	C4—N3—C5—N4	0.3 (5)
N2—N1—C2—C1	0.1 (4)	C6—N4—C5—N3	−0.8 (5)
C3—C1—C2—N1	0.1 (4)	C5—N4—C6—O1	−179.6 (3)
I1—C1—C2—N1	177.7 (2)	C5—N4—C6—C7	0.3 (4)
N1—N2—C3—C1	0.4 (3)	C8—O1—C6—N4	−0.6 (4)
C4—N2—C3—C1	178.1 (3)	C8—O1—C6—C7	179.6 (2)
C2—C1—C3—N2	−0.3 (3)	N3—C4—C7—C6	−1.3 (4)
I1—C1—C3—N2	−177.96 (19)	N2—C4—C7—C6	179.4 (2)
C5—N3—C4—C7	0.8 (4)	N4—C6—C7—C4	0.7 (4)
C5—N3—C4—N2	−179.8 (3)	O1—C6—C7—C4	−179.5 (2)
C3—N2—C4—N3	7.6 (4)	C6—O1—C8—C9	84.8 (3)
N1—N2—C4—N3	−174.8 (3)	O1—C8—C9—C10	177.7 (2)
C3—N2—C4—C7	−173.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.95	2.40	3.249 (4)	148
C11—H11···N4ii	0.95	2.52	3.392 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.95	2.40	3.249 (4)	148
C11—H11⋯N4ii	0.95	2.52	3.392 (4)	153

Symmetry codes: (i) ; (ii) .