Ethyl 1-(2,6-difluoro-benz-yl)-1H-1,2,3-triazole-4-carboxyl-ate.

In the title compound, C(12)H(11)F(2)N(3)O(2), the dihedral angle between the triazole and phenyl rings is 73.74 (9)°. In the crystal, mol-ecules are linked into chains along [010] via weak C-H⋯O and C-H⋯N hydrogen bonds.

Related literature

The title compound is an inter­mediate in the synthesis of rufinamide, a new anti-epilepsy drug (Herranz, 2008 ▶). For synthetic procedures, see: Abu-Orabi et al. (1989 ▶); Wang & Xie (2004 ▶). For a related structure, see: Xiao et al. (2008 ▶).

Experimental

Crystal data

C12H11F2N3O2

M = 267.24

Monoclinic,

a = 9.4540 (19) Å

b = 10.963 (2) Å

c = 12.167 (2) Å

β = 93.21 (3)°

V = 1259.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.965, T max = 0.977

3270 measured reflections

2316 independent reflections

1629 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.163

S = 1.03

2316 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050014/pv2364sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050014/pv2364Isup2.hkl

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

C12H11F2N3O2	F(000) = 552
Mr = 267.24	Dx = 1.410 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.4540 (19) Å	θ = 9–13°
b = 10.963 (2) Å	µ = 0.12 mm−1
c = 12.167 (2) Å	T = 293 K
β = 93.21 (3)°	Block, colorless
V = 1259.1 (4) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1629 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 25.4°, θmin = 2.2°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −3→13
Tmin = 0.965, Tmax = 0.977	l = −14→14
3270 measured reflections	3 standard reflections every 200 reflections
2316 independent reflections	intensity decay: 1%

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0873P)2 + 0.337P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2316 reflections	Δρmax = 0.32 e Å−3
174 parameters	Δρmin = −0.22 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: 0.029 (5)

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
F1	0.94152 (18)	0.27880 (14)	0.02828 (16)	0.0890 (6)
F2	0.78127 (17)	0.61613 (15)	0.22000 (14)	0.0829 (6)
O1	0.4165 (2)	0.20776 (17)	0.46337 (16)	0.0744 (6)
O2	0.3594 (2)	0.39959 (17)	0.41799 (17)	0.0776 (6)
N1	0.62925 (19)	0.35347 (16)	0.16945 (17)	0.0537 (5)
N2	0.6558 (3)	0.2343 (2)	0.1898 (2)	0.0751 (7)
N3	0.5829 (2)	0.20178 (19)	0.2728 (2)	0.0709 (7)
C1	0.9678 (3)	0.3771 (2)	0.0933 (2)	0.0618 (7)
C2	1.1060 (3)	0.4031 (3)	0.1262 (3)	0.0733 (8)
H2	1.1796	0.3538	0.1049	0.088*
C3	1.1325 (3)	0.5034 (3)	0.1910 (3)	0.0751 (8)
H3	1.2252	0.5220	0.2146	0.090*
C4	1.0243 (3)	0.5767 (3)	0.2217 (2)	0.0687 (7)
H4	1.0426	0.6459	0.2644	0.082*
C5	0.8887 (3)	0.5456 (2)	0.1878 (2)	0.0583 (6)
C6	0.8534 (2)	0.4459 (2)	0.12140 (19)	0.0522 (6)
C7	0.7032 (3)	0.4176 (2)	0.0843 (2)	0.0593 (7)
H7B	0.6538	0.4930	0.0658	0.071*
H7A	0.7023	0.3676	0.0185	0.071*
C8	0.5379 (2)	0.3966 (2)	0.2397 (2)	0.0524 (6)
H8	0.5015	0.4753	0.2428	0.063*
C9	0.5093 (2)	0.3001 (2)	0.3059 (2)	0.0538 (6)
C10	0.4248 (3)	0.2941 (2)	0.4032 (2)	0.0577 (6)
C11	0.2781 (4)	0.4100 (3)	0.5169 (3)	0.1053 (13)
H11A	0.2056	0.3473	0.5162	0.126*
H11B	0.3404	0.3988	0.5822	0.126*
C12	0.2137 (4)	0.5286 (3)	0.5186 (3)	0.0955 (11)
H12A	0.1482	0.5373	0.4559	0.143*
H12C	0.2857	0.5901	0.5163	0.143*
H12B	0.1641	0.5376	0.5849	0.143*

	U11	U22	U33	U12	U13	U23
F1	0.0929 (12)	0.0560 (10)	0.1202 (14)	−0.0053 (8)	0.0250 (10)	−0.0258 (9)
F2	0.0797 (11)	0.0754 (11)	0.0936 (12)	0.0159 (9)	0.0056 (9)	−0.0255 (9)
O1	0.0857 (13)	0.0520 (11)	0.0853 (13)	−0.0042 (9)	0.0038 (10)	0.0175 (10)
O2	0.0897 (14)	0.0537 (11)	0.0929 (14)	0.0125 (10)	0.0351 (11)	0.0150 (10)
N1	0.0500 (11)	0.0360 (10)	0.0751 (13)	−0.0006 (8)	0.0039 (9)	−0.0005 (9)
N2	0.0744 (15)	0.0421 (12)	0.1107 (18)	0.0101 (11)	0.0221 (14)	0.0037 (12)
N3	0.0678 (14)	0.0404 (12)	0.1064 (18)	0.0058 (10)	0.0220 (13)	0.0086 (12)
C1	0.0709 (17)	0.0402 (12)	0.0759 (16)	−0.0045 (12)	0.0198 (13)	−0.0027 (11)
C2	0.0581 (16)	0.0583 (17)	0.105 (2)	0.0027 (13)	0.0198 (15)	0.0076 (15)
C3	0.0602 (16)	0.0719 (19)	0.093 (2)	−0.0104 (15)	0.0015 (15)	0.0048 (16)
C4	0.0718 (17)	0.0629 (16)	0.0706 (17)	−0.0111 (14)	−0.0030 (13)	−0.0067 (13)
C5	0.0621 (15)	0.0524 (14)	0.0607 (14)	0.0023 (12)	0.0061 (12)	−0.0008 (11)
C6	0.0562 (13)	0.0444 (12)	0.0563 (13)	−0.0040 (11)	0.0066 (10)	0.0055 (10)
C7	0.0614 (15)	0.0506 (14)	0.0658 (15)	−0.0042 (11)	0.0018 (12)	−0.0001 (12)
C8	0.0439 (12)	0.0359 (12)	0.0769 (16)	0.0018 (9)	−0.0008 (11)	−0.0022 (11)
C9	0.0460 (12)	0.0375 (12)	0.0775 (16)	−0.0028 (10)	−0.0004 (11)	0.0011 (11)
C10	0.0534 (13)	0.0434 (13)	0.0759 (16)	−0.0046 (11)	−0.0003 (12)	0.0039 (12)
C11	0.141 (3)	0.077 (2)	0.103 (3)	0.020 (2)	0.058 (2)	0.0216 (19)
C12	0.105 (2)	0.095 (3)	0.088 (2)	0.018 (2)	0.0283 (18)	0.0080 (19)

F1—C1	1.352 (3)	C4—C5	1.368 (4)
F2—C5	1.352 (3)	C4—H4	0.9300
O1—C10	1.202 (3)	C5—C6	1.390 (3)
O2—C10	1.329 (3)	C6—C7	1.498 (3)
O2—C11	1.468 (4)	C7—H7B	0.9700
N1—C8	1.335 (3)	C7—H7A	0.9700
N1—N2	1.351 (3)	C8—C9	1.366 (3)
N1—C7	1.462 (3)	C8—H8	0.9300
N2—N3	1.304 (3)	C9—C10	1.466 (4)
N3—C9	1.356 (3)	C11—C12	1.437 (4)
C1—C2	1.374 (4)	C11—H11A	0.9700
C1—C6	1.377 (3)	C11—H11B	0.9700
C2—C3	1.368 (4)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C3—C4	1.369 (4)	C12—H12B	0.9600
C3—H3	0.9300
C10—O2—C11	116.6 (2)	C6—C7—H7B	109.3
C8—N1—N2	110.2 (2)	N1—C7—H7A	109.3
C8—N1—C7	129.4 (2)	C6—C7—H7A	109.3
N2—N1—C7	120.2 (2)	H7B—C7—H7A	108.0
N3—N2—N1	107.8 (2)	N1—C8—C9	105.03 (19)
N2—N3—C9	108.3 (2)	N1—C8—H8	127.5
F1—C1—C2	118.4 (2)	C9—C8—H8	127.5
F1—C1—C6	117.4 (2)	N3—C9—C8	108.6 (2)
C2—C1—C6	124.2 (2)	N3—C9—C10	121.0 (2)
C3—C2—C1	118.3 (3)	C8—C9—C10	130.2 (2)
C3—C2—H2	120.8	O1—C10—O2	123.7 (2)
C1—C2—H2	120.8	O1—C10—C9	125.8 (2)
C2—C3—C4	120.9 (3)	O2—C10—C9	110.4 (2)
C2—C3—H3	119.5	C12—C11—O2	108.9 (3)
C4—C3—H3	119.5	C12—C11—H11A	109.9
C5—C4—C3	118.2 (3)	O2—C11—H11A	109.9
C5—C4—H4	120.9	C12—C11—H11B	109.9
C3—C4—H4	120.9	O2—C11—H11B	109.9
F2—C5—C4	118.5 (2)	H11A—C11—H11B	108.3
F2—C5—C6	117.3 (2)	C11—C12—H12A	109.5
C4—C5—C6	124.2 (2)	C11—C12—H12C	109.5
C1—C6—C5	114.1 (2)	H12A—C12—H12C	109.5
C1—C6—C7	123.8 (2)	C11—C12—H12B	109.5
C5—C6—C7	122.0 (2)	H12A—C12—H12B	109.5
N1—C7—C6	111.7 (2)	H12C—C12—H12B	109.5
N1—C7—H7B	109.3
C8—N1—N2—N3	−0.5 (3)	C8—N1—C7—C6	100.9 (3)
C7—N1—N2—N3	176.4 (2)	N2—N1—C7—C6	−75.2 (3)
N1—N2—N3—C9	0.0 (3)	C1—C6—C7—N1	99.0 (3)
F1—C1—C2—C3	179.3 (3)	C5—C6—C7—N1	−81.2 (3)
C6—C1—C2—C3	0.1 (4)	N2—N1—C8—C9	0.7 (3)
C1—C2—C3—C4	−0.6 (4)	C7—N1—C8—C9	−175.8 (2)
C2—C3—C4—C5	1.4 (4)	N2—N3—C9—C8	0.4 (3)
C3—C4—C5—F2	178.5 (3)	N2—N3—C9—C10	−175.6 (2)
C3—C4—C5—C6	−1.9 (4)	N1—C8—C9—N3	−0.7 (3)
F1—C1—C6—C5	−179.7 (2)	N1—C8—C9—C10	174.9 (2)
C2—C1—C6—C5	−0.5 (4)	C11—O2—C10—O1	2.7 (4)
F1—C1—C6—C7	0.1 (4)	C11—O2—C10—C9	−176.0 (3)
C2—C1—C6—C7	179.4 (2)	N3—C9—C10—O1	3.0 (4)
F2—C5—C6—C1	−179.0 (2)	C8—C9—C10—O1	−172.1 (3)
C4—C5—C6—C1	1.4 (4)	N3—C9—C10—O2	−178.3 (2)
F2—C5—C6—C7	1.2 (3)	C8—C9—C10—O2	6.6 (4)
C4—C5—C6—C7	−178.4 (2)	C10—O2—C11—C12	−179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···F1	0.97	2.46	2.833 (3)	103.
C7—H7B···O1i	0.97	2.47	3.415 (3)	166.
C8—H8···N3i	0.93	2.61	3.536 (3)	172.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O1i	0.97	2.47	3.415 (3)	166
C8—H8⋯N3i	0.93	2.61	3.536 (3)	172

Symmetry code: (i) .