1-[4-(Difluoromethoxy)phenyl]-N-(2,3-dimethylphenyl)-1H-1,2,4-triazole-3-carboxamide.

In the mol-ecule of the title compound, C(18)H(16)F(2)N(4)O(2), the 1,2,4-triazole ring forms dihedral angles of 3.6 (2) and 14.9 (6)° with the 4-difluoro-meth-oxy-substituted benzene ring and the 2,3-dimethyl-substituted benzene ring, respectively. The OCHF(2) group is twisted away from the plane of the benzene ring, as shown by the C-O-C-C torsion angle of 145.8 (2)°. The conformation is stabilized by an inter-molecular N-H⋯N hydrogen bond. In the crystal, short C-H⋯O inter-actions lead to chains of mol-ecules.

Related literature

For general background regarding the biological and pharmacological activities of 1,2,4-triazoles and their derivatives, see: Wahbi et al. (1995 ▶); Chai et al. (2003 ▶); Hashimoto et al. (1990 ▶); Kalluraya et al. (1996 ▶); Almasirad et al. (2004 ▶); Amir & Shikha (2004 ▶); Kanazawa et al. (1988 ▶); Vlasova et al. (1971 ▶); Labanauskas et al. (2004 ▶); Tozkoparan et al. (2007 ▶). For a related synthesis, see: Drutkowski et al. (2002 ▶); Frohberg et al. (2002 ▶).

Experimental

Crystal data

C18H16F2N4O2

M = 358.35

Triclinic,

a = 7.5543 (10) Å

b = 7.8132 (10) Å

c = 14.8190 (19) Å

α = 95.974 (2)°

β = 98.593 (1)°

γ = 101.523 (1)°

V = 839.28 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.49 × 0.31 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.948, T max = 0.990

6446 measured reflections

3115 independent reflections

2366 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.123

S = 1.06

3115 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks wyg, I. DOI: 10.1107/S160053680901263X/ez2162sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901263X/ez2162Isup2.hkl

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

C18H16F2N4O2	V = 839.28 (19) Å3
Mr = 358.35	Z = 2
Triclinic, P1	F(000) = 372
a = 7.5543 (10) Å	Dx = 1.418 Mg m−3
b = 7.8132 (10) Å	Mo Kα radiation, λ = 0.71073 Å
c = 14.8190 (19) Å	µ = 0.11 mm−1
α = 95.974 (2)°	T = 296 K
β = 98.593 (1)°	Block, white
γ = 101.523 (1)°	0.49 × 0.31 × 0.10 mm

Bruker APEXII CCD diffractometer	3115 independent reflections
Radiation source: fine-focus sealed tube	2366 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.948, Tmax = 0.990	k = −9→9
6446 measured reflections	l = −17→17

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.1647P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3115 reflections	Δρmax = 0.23 e Å−3
238 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (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
F1	−0.9182 (2)	0.3392 (2)	0.14577 (12)	0.1146 (6)
F2	−0.8560 (2)	0.1332 (2)	0.05859 (11)	0.1113 (6)
O1	−0.6301 (2)	0.3298 (2)	0.13688 (9)	0.0742 (4)
O2	0.41124 (16)	0.80678 (19)	0.54210 (9)	0.0634 (4)
N1	−0.15235 (18)	0.67315 (18)	0.45595 (9)	0.0458 (4)
N2	0.03287 (19)	0.69741 (19)	0.46115 (10)	0.0472 (4)
N3	−0.0355 (2)	0.8275 (2)	0.59091 (11)	0.0663 (5)
N4	0.32482 (19)	0.9655 (2)	0.66010 (10)	0.0513 (4)
H4D	0.2285	0.9901	0.6779	0.062*
C1	−0.7981 (3)	0.2345 (3)	0.13967 (17)	0.0766 (7)
H1	−0.7944	0.1632	0.1903	0.092*
C2	−0.5184 (3)	0.4106 (2)	0.21999 (13)	0.0541 (5)
C3	−0.3332 (3)	0.4212 (3)	0.22448 (13)	0.0611 (5)
H3	−0.2899	0.3708	0.1749	0.073*
C4	−0.2118 (3)	0.5063 (3)	0.30237 (13)	0.0556 (5)
H4	−0.0866	0.5130	0.3057	0.067*
C5	−0.2770 (2)	0.5815 (2)	0.37546 (11)	0.0444 (4)
C6	−0.4633 (2)	0.5707 (2)	0.37090 (13)	0.0539 (5)
H6	−0.5069	0.6212	0.4203	0.065*
C7	−0.5839 (3)	0.4846 (3)	0.29260 (13)	0.0577 (5)
H7	−0.7093	0.4768	0.2891	0.069*
C8	−0.1882 (3)	0.7512 (3)	0.53408 (14)	0.0649 (6)
H8	−0.3053	0.7513	0.5464	0.078*
C9	0.0950 (2)	0.7909 (2)	0.54299 (11)	0.0460 (4)
C10	0.2942 (2)	0.8537 (2)	0.58047 (11)	0.0448 (4)
C11	0.4936 (2)	1.0475 (2)	0.71818 (12)	0.0464 (4)
C12	0.6569 (2)	1.0709 (2)	0.68418 (13)	0.0538 (5)
H12	0.6575	1.0310	0.6229	0.065*
C13	0.8177 (3)	1.1539 (3)	0.74204 (14)	0.0599 (5)
H13	0.9280	1.1682	0.7200	0.072*
C14	0.8166 (3)	1.2157 (3)	0.83215 (14)	0.0629 (5)
H14	0.9266	1.2713	0.8704	0.076*
C15	0.6546 (3)	1.1965 (3)	0.86695 (13)	0.0572 (5)
C16	0.4892 (2)	1.1100 (2)	0.80967 (12)	0.0506 (4)
C17	0.6597 (3)	1.2699 (3)	0.96572 (15)	0.0823 (7)
H17A	0.7840	1.3231	0.9941	0.124*
H17B	0.6118	1.1762	0.9984	0.124*
H17C	0.5864	1.3570	0.9675	0.124*
C18	0.3094 (3)	1.0884 (3)	0.84471 (14)	0.0703 (6)
H18A	0.2420	1.1706	0.8208	0.105*
H18B	0.3330	1.1105	0.9108	0.105*
H18C	0.2389	0.9703	0.8248	0.105*

	U11	U22	U33	U12	U13	U23
F1	0.0681 (9)	0.1287 (13)	0.1263 (13)	0.0247 (9)	−0.0216 (9)	−0.0270 (10)
F2	0.1052 (12)	0.1003 (11)	0.0926 (11)	−0.0021 (9)	−0.0311 (9)	−0.0318 (8)
O1	0.0631 (9)	0.0896 (11)	0.0523 (8)	0.0000 (8)	−0.0083 (7)	−0.0111 (7)
O2	0.0403 (7)	0.0849 (10)	0.0585 (8)	0.0131 (7)	0.0075 (6)	−0.0162 (7)
N1	0.0359 (8)	0.0537 (8)	0.0444 (8)	0.0091 (6)	0.0045 (6)	−0.0034 (6)
N2	0.0356 (8)	0.0569 (9)	0.0460 (8)	0.0084 (6)	0.0055 (6)	−0.0017 (7)
N3	0.0412 (9)	0.0964 (13)	0.0542 (10)	0.0167 (8)	0.0046 (7)	−0.0201 (9)
N4	0.0378 (8)	0.0640 (10)	0.0482 (9)	0.0110 (7)	0.0053 (6)	−0.0065 (7)
C1	0.0699 (15)	0.0672 (14)	0.0725 (15)	0.0012 (12)	−0.0212 (11)	−0.0079 (11)
C2	0.0521 (11)	0.0548 (11)	0.0466 (10)	0.0044 (8)	−0.0037 (8)	−0.0005 (8)
C3	0.0570 (12)	0.0698 (13)	0.0502 (11)	0.0090 (10)	0.0090 (9)	−0.0105 (9)
C4	0.0431 (10)	0.0625 (11)	0.0562 (11)	0.0076 (8)	0.0075 (8)	−0.0050 (9)
C5	0.0410 (9)	0.0456 (9)	0.0425 (9)	0.0072 (7)	0.0015 (7)	0.0009 (7)
C6	0.0436 (10)	0.0648 (12)	0.0495 (11)	0.0138 (9)	0.0027 (8)	−0.0050 (9)
C7	0.0410 (10)	0.0693 (12)	0.0582 (12)	0.0123 (9)	−0.0005 (8)	−0.0001 (9)
C8	0.0379 (10)	0.0943 (15)	0.0557 (11)	0.0151 (10)	0.0055 (8)	−0.0180 (10)
C9	0.0397 (9)	0.0541 (10)	0.0428 (9)	0.0117 (8)	0.0056 (7)	−0.0004 (8)
C10	0.0396 (9)	0.0511 (10)	0.0421 (9)	0.0100 (7)	0.0054 (7)	0.0012 (7)
C11	0.0413 (9)	0.0497 (10)	0.0451 (10)	0.0091 (7)	0.0030 (7)	0.0013 (8)
C12	0.0469 (10)	0.0614 (11)	0.0496 (10)	0.0084 (8)	0.0078 (8)	−0.0010 (8)
C13	0.0433 (10)	0.0661 (12)	0.0638 (12)	0.0047 (9)	0.0059 (9)	−0.0008 (10)
C14	0.0485 (11)	0.0651 (12)	0.0638 (13)	0.0056 (9)	−0.0084 (9)	−0.0033 (10)
C15	0.0601 (12)	0.0597 (11)	0.0472 (10)	0.0145 (9)	−0.0024 (9)	0.0008 (9)
C16	0.0514 (10)	0.0557 (11)	0.0436 (10)	0.0150 (8)	0.0037 (8)	0.0018 (8)
C17	0.0873 (17)	0.0976 (18)	0.0509 (12)	0.0169 (14)	−0.0047 (11)	−0.0101 (11)
C18	0.0616 (13)	0.0961 (16)	0.0510 (12)	0.0169 (11)	0.0128 (10)	−0.0033 (11)

F1—C1	1.345 (3)	C6—C7	1.381 (2)
F2—C1	1.330 (3)	C6—H6	0.9300
O1—C1	1.346 (3)	C7—H7	0.9300
O1—C2	1.394 (2)	C8—H8	0.9300
O2—C10	1.215 (2)	C9—C10	1.487 (2)
N1—C8	1.341 (2)	C11—C12	1.387 (2)
N1—N2	1.3632 (19)	C11—C16	1.400 (2)
N1—C5	1.428 (2)	C12—C13	1.374 (3)
N2—C9	1.316 (2)	C12—H12	0.9300
N3—C8	1.314 (2)	C13—C14	1.374 (3)
N3—C9	1.355 (2)	C13—H13	0.9300
N4—C10	1.353 (2)	C14—C15	1.385 (3)
N4—C11	1.417 (2)	C14—H14	0.9300
N4—H4D	0.8600	C15—C16	1.402 (3)
C1—H1	0.9800	C15—C17	1.507 (3)
C2—C7	1.372 (3)	C16—C18	1.510 (3)
C2—C3	1.376 (3)	C17—H17A	0.9600
C3—C4	1.377 (3)	C17—H17B	0.9600
C3—H3	0.9300	C17—H17C	0.9600
C4—C5	1.380 (2)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.384 (2)	C18—H18C	0.9600
C1—O1—C2	118.10 (17)	N2—C9—N3	115.33 (15)
C8—N1—N2	109.18 (14)	N2—C9—C10	122.68 (15)
C8—N1—C5	129.19 (15)	N3—C9—C10	121.99 (15)
N2—N1—C5	121.60 (13)	O2—C10—N4	125.87 (16)
C9—N2—N1	102.16 (13)	O2—C10—C9	122.19 (15)
C8—N3—C9	102.47 (15)	N4—C10—C9	111.94 (14)
C10—N4—C11	129.00 (15)	C12—C11—C16	121.23 (16)
C10—N4—H4D	115.5	C12—C11—N4	120.80 (16)
C11—N4—H4D	115.5	C16—C11—N4	117.93 (15)
F2—C1—F1	105.50 (18)	C13—C12—C11	119.26 (17)
F2—C1—O1	106.7 (2)	C13—C12—H12	120.4
F1—C1—O1	110.9 (2)	C11—C12—H12	120.4
F2—C1—H1	111.2	C14—C13—C12	120.48 (18)
F1—C1—H1	111.2	C14—C13—H13	119.8
O1—C1—H1	111.2	C12—C13—H13	119.8
C7—C2—C3	120.57 (17)	C13—C14—C15	121.14 (18)
C7—C2—O1	123.26 (18)	C13—C14—H14	119.4
C3—C2—O1	116.09 (17)	C15—C14—H14	119.4
C2—C3—C4	120.04 (18)	C14—C15—C16	119.45 (18)
C2—C3—H3	120.0	C14—C15—C17	119.27 (19)
C4—C3—H3	120.0	C16—C15—C17	121.28 (19)
C3—C4—C5	119.59 (18)	C11—C16—C15	118.43 (17)
C3—C4—H4	120.2	C11—C16—C18	120.51 (16)
C5—C4—H4	120.2	C15—C16—C18	121.04 (17)
C4—C5—C6	120.32 (16)	C15—C17—H17A	109.5
C4—C5—N1	120.17 (15)	C15—C17—H17B	109.5
C6—C5—N1	119.50 (15)	H17A—C17—H17B	109.5
C7—C6—C5	119.65 (17)	C15—C17—H17C	109.5
C7—C6—H6	120.2	H17A—C17—H17C	109.5
C5—C6—H6	120.2	H17B—C17—H17C	109.5
C2—C7—C6	119.82 (18)	C16—C18—H18A	109.5
C2—C7—H7	120.1	C16—C18—H18B	109.5
C6—C7—H7	120.1	H18A—C18—H18B	109.5
N3—C8—N1	110.85 (16)	C16—C18—H18C	109.5
N3—C8—H8	124.6	H18A—C18—H18C	109.5
N1—C8—H8	124.6	H18B—C18—H18C	109.5
C8—N1—N2—C9	−0.5 (2)	C8—N3—C9—N2	−0.1 (2)
C5—N1—N2—C9	177.77 (15)	C8—N3—C9—C10	179.36 (18)
C2—O1—C1—F2	−162.99 (17)	C11—N4—C10—O2	−2.5 (3)
C2—O1—C1—F1	82.6 (2)	C11—N4—C10—C9	177.38 (16)
C1—O1—C2—C7	−37.5 (3)	N2—C9—C10—O2	−8.1 (3)
C1—O1—C2—C3	145.8 (2)	N3—C9—C10—O2	172.46 (18)
C7—C2—C3—C4	0.1 (3)	N2—C9—C10—N4	172.08 (16)
O1—C2—C3—C4	176.96 (18)	N3—C9—C10—N4	−7.4 (2)
C2—C3—C4—C5	−0.4 (3)	C10—N4—C11—C12	22.9 (3)
C3—C4—C5—C6	0.4 (3)	C10—N4—C11—C16	−159.57 (17)
C3—C4—C5—N1	−178.75 (17)	C16—C11—C12—C13	1.4 (3)
C8—N1—C5—C4	−178.5 (2)	N4—C11—C12—C13	178.84 (17)
N2—N1—C5—C4	3.6 (2)	C11—C12—C13—C14	−1.1 (3)
C8—N1—C5—C6	2.4 (3)	C12—C13—C14—C15	−0.1 (3)
N2—N1—C5—C6	−175.54 (16)	C13—C14—C15—C16	1.1 (3)
C4—C5—C6—C7	−0.2 (3)	C13—C14—C15—C17	−178.7 (2)
N1—C5—C6—C7	178.98 (16)	C12—C11—C16—C15	−0.4 (3)
C3—C2—C7—C6	0.1 (3)	N4—C11—C16—C15	−177.95 (16)
O1—C2—C7—C6	−176.50 (17)	C12—C11—C16—C18	178.06 (18)
C5—C6—C7—C2	−0.1 (3)	N4—C11—C16—C18	0.5 (3)
C9—N3—C8—N1	−0.2 (2)	C14—C15—C16—C11	−0.8 (3)
N2—N1—C8—N3	0.5 (2)	C17—C15—C16—C11	178.95 (19)
C5—N1—C8—N3	−177.64 (17)	C14—C15—C16—C18	−179.26 (19)
N1—N2—C9—N3	0.4 (2)	C17—C15—C16—C18	0.5 (3)
N1—N2—C9—C10	−179.09 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4D···N3	0.86	2.27	2.717 (2)	113
C6—H6···O2i	0.93	2.43	3.344 (2)	169
C8—H8···O2i	0.93	2.26	3.159 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4D⋯N3	0.86	2.27	2.717 (2)	113
C6—H6⋯O2i	0.93	2.43	3.344 (2)	169
C8—H8⋯O2i	0.93	2.26	3.159 (2)	162

Symmetry code: (i) .