2-tert-Butyl-4-chloro-5-[4-(2-fluoro-eth-oxy)benz-yloxy]pyridazin-3(2H)-one.

In the title compound, C(17)H(20)ClFN(2)O(3), the dihedral angle between the pyridazine and benzene rings is 41.37 (10)°. In the crystal, there are no significant intermolecular interactions present. The terminal -CH(2)F group is disordered over two sets of sites with an occupancy ratio of 0.737 (2):0.263 (2).

Related literature

For details of the synthesis, see: Mou et al. (2010 ▶, 2012 ▶). For possible applications of the title compound as a myocardial perfusion imaging agent for positron emission tomography (when labelled with 18F), see: Mou et al. (2011 ▶); Mou et al. (2012 ▶).

Experimental

Crystal data

C17H20ClFN2O3

M = 354.80

Triclinic,

a = 8.7170 (14) Å

b = 9.5850 (16) Å

c = 11.8524 (19) Å

α = 110.475 (2)°

β = 107.185 (2)°

γ = 96.424 (3)°

V = 860.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 150 K

0.47 × 0.38 × 0.35 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.892, T max = 0.918

4337 measured reflections

3090 independent reflections

2788 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.05

3090 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812020491/aa2046sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020491/aa2046Isup4.hkl

Supplementary material file. DOI: 10.1107/S1600536812020491/aa2046Isup3.cml

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

C17H20ClFN2O3	Z = 2
Mr = 354.80	F(000) = 372
Triclinic, P1	Dx = 1.370 Mg m−3
Hall symbol: -P 1	Melting point: 396 K
a = 8.7170 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5850 (16) Å	Cell parameters from 2518 reflections
c = 11.8524 (19) Å	θ = 2.3–27.5°
α = 110.475 (2)°	µ = 0.25 mm−1
β = 107.185 (2)°	T = 150 K
γ = 96.424 (3)°	Column, colourless, colourless
V = 860.3 (2) Å3	0.47 × 0.38 × 0.35 mm

Bruker APEXII CCD area-detector diffractometer	3090 independent reflections
Radiation source: fine-focus sealed tube	2788 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
phi and ω scans	θmax = 25.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→10
Tmin = 0.892, Tmax = 0.918	k = −11→10
4337 measured reflections	l = −14→13

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.4066P] where P = (Fo2 + 2Fc2)/3
3090 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
C1	0.7610 (4)	1.6895 (3)	0.6672 (3)	0.0356 (7)	0.737 (2)
H1A	0.7483	1.7463	0.7502	0.043*	0.737 (2)
H1B	0.8756	1.7279	0.6751	0.043*	0.737 (2)
F1	0.6489 (2)	1.71415 (19)	0.56807 (19)	0.0563 (5)	0.737 (2)
C1A	0.6652 (12)	1.6621 (10)	0.6292 (9)	0.0356 (7)	0.263 (2)
H1A1	0.5919	1.6389	0.5400	0.043*	0.263 (2)
H1A2	0.6036	1.6957	0.6880	0.043*	0.263 (2)
F1A	0.8073 (7)	1.7730 (6)	0.6664 (5)	0.0563 (5)	0.263 (2)
C2	0.7295 (3)	1.5215 (2)	0.63796 (19)	0.0357 (5)
H2A	0.7927	1.5042	0.7142	0.043*
H2B	0.6104	1.4780	0.6141	0.043*
C3	0.7804 (2)	1.29834 (18)	0.49589 (16)	0.0253 (4)
C4	0.8406 (2)	1.2381 (2)	0.39752 (17)	0.0301 (4)
H4	0.8787	1.3019	0.3607	0.036*
C5	0.8452 (2)	1.08544 (19)	0.35314 (16)	0.0278 (4)
H5	0.8883	1.0456	0.2867	0.033*
C6	0.7879 (2)	0.98912 (18)	0.40407 (15)	0.0224 (4)
C7	0.7268 (2)	1.05060 (19)	0.50116 (16)	0.0267 (4)
H7	0.6861	0.9860	0.5363	0.032*
C8	0.7234 (2)	1.2049 (2)	0.54876 (17)	0.0276 (4)
H8	0.6827	1.2454	0.6165	0.033*
C9	0.7940 (2)	0.82347 (19)	0.35594 (16)	0.0271 (4)
H9A	0.9074	0.8134	0.3944	0.032*
H9B	0.7176	0.7643	0.3796	0.032*
C10	0.74817 (19)	0.62230 (17)	0.15061 (16)	0.0205 (3)
C11	0.69499 (19)	0.56701 (17)	0.01958 (15)	0.0196 (3)
C12	0.69623 (19)	0.41371 (18)	−0.05951 (15)	0.0205 (3)
C13	0.8067 (2)	0.52043 (18)	0.20730 (16)	0.0244 (4)
H13	0.8450	0.5560	0.2986	0.029*
C14	0.7659 (2)	0.16475 (18)	−0.05844 (16)	0.0224 (4)
C15	0.8931 (2)	0.1704 (2)	−0.12319 (19)	0.0319 (4)
H15A	0.8604	0.2209	−0.1825	0.048*
H15B	0.8984	0.0657	−0.1714	0.048*
H15C	1.0020	0.2281	−0.0571	0.048*
C16	0.5943 (2)	0.06939 (19)	−0.15633 (18)	0.0324 (4)
H16A	0.5141	0.0780	−0.1127	0.049*
H16B	0.5978	−0.0383	−0.1945	0.049*
H16C	0.5612	0.1075	−0.2244	0.049*
C17	0.8217 (2)	0.09524 (19)	0.03935 (18)	0.0308 (4)
H17A	0.9307	0.1564	0.1034	0.046*
H17B	0.8286	−0.0101	−0.0049	0.046*
H17C	0.7419	0.0946	0.0827	0.046*
Cl1	0.62207 (5)	0.67867 (4)	−0.06075 (4)	0.02475 (13)
N1	0.75585 (16)	0.32789 (14)	0.01074 (12)	0.0199 (3)
N2	0.81035 (17)	0.38114 (15)	0.14042 (13)	0.0241 (3)
O1	0.78194 (18)	1.45135 (14)	0.53292 (12)	0.0356 (3)
O2	0.74477 (15)	0.76678 (12)	0.21681 (10)	0.0246 (3)
O3	0.64984 (16)	0.36158 (13)	−0.17774 (11)	0.0292 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0526 (19)	0.0305 (15)	0.0392 (17)	0.0225 (17)	0.0274 (16)	0.0189 (13)
F1	0.0628 (11)	0.0390 (9)	0.0698 (12)	0.0205 (8)	0.0142 (9)	0.0304 (9)
C1A	0.0526 (19)	0.0305 (15)	0.0392 (17)	0.0225 (17)	0.0274 (16)	0.0189 (13)
F1A	0.0628 (11)	0.0390 (9)	0.0698 (12)	0.0205 (8)	0.0142 (9)	0.0304 (9)
C2	0.0596 (13)	0.0248 (9)	0.0333 (10)	0.0188 (9)	0.0280 (10)	0.0119 (8)
C3	0.0340 (10)	0.0181 (8)	0.0221 (8)	0.0079 (7)	0.0098 (7)	0.0057 (7)
C4	0.0469 (11)	0.0229 (9)	0.0271 (9)	0.0100 (8)	0.0203 (8)	0.0114 (7)
C5	0.0380 (10)	0.0247 (9)	0.0220 (9)	0.0098 (7)	0.0151 (8)	0.0068 (7)
C6	0.0266 (9)	0.0197 (8)	0.0159 (8)	0.0058 (7)	0.0038 (7)	0.0048 (6)
C7	0.0355 (10)	0.0225 (8)	0.0239 (9)	0.0055 (7)	0.0131 (7)	0.0097 (7)
C8	0.0378 (10)	0.0253 (9)	0.0225 (9)	0.0104 (7)	0.0160 (8)	0.0075 (7)
C9	0.0376 (10)	0.0228 (9)	0.0176 (8)	0.0094 (7)	0.0076 (7)	0.0059 (7)
C10	0.0196 (8)	0.0163 (7)	0.0229 (8)	0.0034 (6)	0.0071 (7)	0.0057 (7)
C11	0.0197 (8)	0.0184 (8)	0.0220 (8)	0.0052 (6)	0.0076 (6)	0.0095 (7)
C12	0.0212 (8)	0.0206 (8)	0.0207 (8)	0.0056 (6)	0.0095 (7)	0.0077 (7)
C13	0.0294 (9)	0.0203 (8)	0.0178 (8)	0.0068 (7)	0.0044 (7)	0.0042 (7)
C14	0.0243 (8)	0.0166 (8)	0.0237 (9)	0.0072 (6)	0.0085 (7)	0.0046 (7)
C15	0.0329 (10)	0.0327 (10)	0.0375 (10)	0.0167 (8)	0.0188 (8)	0.0147 (8)
C16	0.0280 (10)	0.0188 (8)	0.0366 (10)	0.0057 (7)	0.0058 (8)	0.0003 (8)
C17	0.0422 (11)	0.0195 (8)	0.0308 (10)	0.0119 (8)	0.0126 (8)	0.0094 (7)
Cl1	0.0323 (2)	0.0221 (2)	0.0243 (2)	0.01014 (16)	0.01102 (17)	0.01263 (17)
N1	0.0233 (7)	0.0167 (7)	0.0173 (7)	0.0053 (5)	0.0062 (6)	0.0048 (5)
N2	0.0277 (8)	0.0217 (7)	0.0188 (7)	0.0063 (6)	0.0046 (6)	0.0065 (6)
O1	0.0646 (9)	0.0198 (6)	0.0329 (7)	0.0160 (6)	0.0302 (7)	0.0104 (5)
O2	0.0353 (7)	0.0166 (6)	0.0177 (6)	0.0091 (5)	0.0069 (5)	0.0035 (5)
O3	0.0432 (7)	0.0261 (6)	0.0187 (6)	0.0131 (5)	0.0117 (5)	0.0075 (5)

C1—F1	1.400 (4)	C9—H9B	0.9900
C1—C2	1.497 (3)	C10—O2	1.3405 (19)
C1—H1A	0.9900	C10—C11	1.361 (2)
C1—H1B	0.9900	C10—C13	1.426 (2)
C1A—F1A	1.383 (11)	C11—C12	1.444 (2)
C1A—C2	1.541 (9)	C11—Cl1	1.7215 (16)
C1A—H1A1	0.9900	C12—O3	1.2276 (19)
C1A—H1A2	0.9900	C12—N1	1.400 (2)
C2—O1	1.425 (2)	C13—N2	1.302 (2)
C2—H2A	0.9900	C13—H13	0.9500
C2—H2B	0.9900	C14—N1	1.5169 (19)
C3—O1	1.373 (2)	C14—C17	1.518 (2)
C3—C8	1.385 (2)	C14—C15	1.529 (2)
C3—C4	1.388 (2)	C14—C16	1.531 (2)
C4—C5	1.381 (2)	C15—H15A	0.9800
C4—H4	0.9500	C15—H15B	0.9800
C5—C6	1.390 (2)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.383 (2)	C16—H16B	0.9800
C6—C9	1.501 (2)	C16—H16C	0.9800
C7—C8	1.393 (2)	C17—H17A	0.9800
C7—H7	0.9500	C17—H17B	0.9800
C8—H8	0.9500	C17—H17C	0.9800
C9—O2	1.450 (2)	N1—N2	1.3469 (18)
C9—H9A	0.9900
F1—C1—C2	109.6 (2)	H9A—C9—H9B	108.6
F1—C1—H1A	109.8	O2—C10—C11	118.74 (14)
C2—C1—H1A	109.8	O2—C10—C13	124.85 (14)
F1—C1—H1B	109.8	C11—C10—C13	116.40 (14)
C2—C1—H1B	109.8	C10—C11—C12	122.61 (14)
H1A—C1—H1B	108.2	C10—C11—Cl1	121.01 (12)
F1A—C1A—C2	103.9 (6)	C12—C11—Cl1	116.38 (12)
F1A—C1A—H1A1	111.0	O3—C12—N1	122.25 (14)
C2—C1A—H1A1	111.0	O3—C12—C11	123.81 (15)
F1A—C1A—H1A2	111.0	N1—C12—C11	113.94 (14)
C2—C1A—H1A2	111.0	N2—C13—C10	123.44 (15)
H1A1—C1A—H1A2	109.0	N2—C13—H13	118.3
O1—C2—C1	106.72 (17)	C10—C13—H13	118.3
O1—C2—C1A	110.7 (4)	N1—C14—C17	109.19 (13)
O1—C2—H2A	110.4	N1—C14—C15	108.07 (13)
C1—C2—H2A	110.4	C17—C14—C15	109.53 (14)
C1A—C2—H2A	130.3	N1—C14—C16	109.30 (13)
O1—C2—H2B	110.4	C17—C14—C16	108.73 (14)
C1—C2—H2B	110.4	C15—C14—C16	111.99 (15)
C1A—C2—H2B	81.7	C14—C15—H15A	109.5
H2A—C2—H2B	108.6	C14—C15—H15B	109.5
O1—C3—C8	124.76 (15)	H15A—C15—H15B	109.5
O1—C3—C4	115.27 (15)	C14—C15—H15C	109.5
C8—C3—C4	119.97 (15)	H15A—C15—H15C	109.5
C5—C4—C3	120.07 (16)	H15B—C15—H15C	109.5
C5—C4—H4	120.0	C14—C16—H16A	109.5
C3—C4—H4	120.0	C14—C16—H16B	109.5
C4—C5—C6	121.06 (16)	H16A—C16—H16B	109.5
C4—C5—H5	119.5	C14—C16—H16C	109.5
C6—C5—H5	119.5	H16A—C16—H16C	109.5
C7—C6—C5	118.15 (15)	H16B—C16—H16C	109.5
C7—C6—C9	121.02 (15)	C14—C17—H17A	109.5
C5—C6—C9	120.83 (15)	C14—C17—H17B	109.5
C6—C7—C8	121.73 (16)	H17A—C17—H17B	109.5
C6—C7—H7	119.1	C14—C17—H17C	109.5
C8—C7—H7	119.1	H17A—C17—H17C	109.5
C3—C8—C7	119.02 (16)	H17B—C17—H17C	109.5
C3—C8—H8	120.5	N2—N1—C12	124.27 (13)
C7—C8—H8	120.5	N2—N1—C14	115.40 (12)
O2—C9—C6	107.02 (13)	C12—N1—C14	120.33 (13)
O2—C9—H9A	110.3	C13—N2—N1	119.34 (14)
C6—C9—H9A	110.3	C3—O1—C2	117.83 (13)
O2—C9—H9B	110.3	C10—O2—C9	118.79 (12)
C6—C9—H9B	110.3