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

Wang, Y.-G.; Huang, G.-B.; Zhu, B.-C.

doi:10.1107/S160053680901263X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1015-o1016

doi:10.1107/S160053680901263X

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

Yu-Guang Wang,^a ^* Guo-Bo Huang ^b and Bing-Chun Zhu ^c,^d

^aCollege of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, ^bSchool of Pharmaceutial and Chemical Engineering, Taizhou University, Taizhou 317000, People's Republic of China, ^cZhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^dZhejiang Research Institute of Chemical Industry, Hangzhou 310023, People's Republic of China
^*Correspondence e-mail: yuguangw@zjut.edu.cn

(Received 23 January 2009; accepted 3 April 2009; online 10 April 2009)

In the molecule of the title compound, C₁₈H₁₆F₂N₄O₂, the 1,2,4-triazole ring forms dihedral angles of 3.6 (2) and 14.9 (6)° with the 4-difluoromethoxy-substituted benzene ring and the 2,3-dimethyl-substituted benzene ring, respectively. The OCHF₂ 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 intermolecular N—H⋯N hydrogen bond. In the crystal, short C—H⋯O interactions lead to chains of molecules.

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_r = 358.35
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.123
S = 1.06
3115 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) x-1, y, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

1,2,4-Triazoles and their derivatives have long been known to exhibit diverse biological and pharmacological activities, such as antitubercular, anticancer (Vlasova et al., 1971; Kalluraya et al., 1996), anticonvulsant (Almasirad et al., 2004; Kanazawa et al., 1988; Chai et al., 2003; Hashimoto et al., 1990), anti-inflammatory (Labanauskas et al. ,2004), herbicidal, and analgesic properties (Tozkoparan et al., 2007; Amir & Shikha, 2004). Also, antifungal activity of aromatic ethers possessing a 1H-1,2,4-triazole ring has been reported (Wahbi et al., 1995). Herein, we report the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound (Fig. 1) the bond lengths and angles are generally within normal ranges. The planar 1,2,4-triazole ring is oriented at dihedral angles of 3.6 (2)° and 14.9 (6)° with respect to the 4-difluoromethoxy-substituted benzene ring and 2,3-dimethyl-substituted benzene ring, respectively. The CHF₂ group is twisted away from the plane of the benzene ring, as shown by the C1—O1—C2—C3 torsion angle [145.8 (2)°].

Related literature top

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 related syntheses, see: Drutkowski et al. (2002); Frohberg et al. (2002).

Experimental top

The general procedure to synthesize the title compound: 2-amine-N-(2,3-dimethyl-phenyl)-2-[(4-difluoromethoxy- phenyl)hydrazono]acetamide (10 mmol), 1.5 mL of a 37%-solution of formaldehyde (20 mmol) and 0.1 g p-toluene sulfonic acid were refluxed in approximately 50 mL ethanol. The reaction was complete after 10 h. The mixture was cooled to room temperature and the solvent was evaporated. The solid product was collected and recrystallized from 2-propanol (Drutkowski et al., 2002; Frohberg et al., 2002).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the title compound showing the atom numbering scheme and the ellipsoids at the 50% probability level.

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

Crystal data top

C₁₈H₁₆F₂N₄O₂	V = 839.28 (19) Å³
M_r = 358.35	Z = 2
Triclinic, P1	F(000) = 372
a = 7.5543 (10) Å	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	3115 independent reflections
Radiation source: fine-focus sealed tube	2366 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
T_min = 0.948, T_max = 0.990	k = −9→9
6446 measured reflections	l = −17→17

Refinement top

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(F_o²) + (0.0593P)² + 0.1647P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3115 reflections	Δρ_max = 0.23 e Å⁻³
238 parameters	Δρ_min = −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)

Crystal data top

C₁₈H₁₆F₂N₄O₂	γ = 101.523 (1)°
M_r = 358.35	V = 839.28 (19) Å³
Triclinic, P1	Z = 2
a = 7.5543 (10) Å	Mo Kα radiation
b = 7.8132 (10) Å	µ = 0.11 mm⁻¹
c = 14.8190 (19) Å	T = 296 K
α = 95.974 (2)°	0.49 × 0.31 × 0.10 mm
β = 98.593 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3115 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2366 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.990	R_int = 0.017
6446 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
3115 reflections	Δρ_min = −0.21 e Å⁻³
238 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆F₂N₄O₂
M_r	358.35
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5543 (10), 7.8132 (10), 14.8190 (19)
α, β, γ (°)	95.974 (2), 98.593 (1), 101.523 (1)
V (Å³)	839.28 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.49 × 0.31 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.948, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	6446, 3115, 2366
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.123, 1.06
No. of reflections	3115
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4D···N3	0.86	2.27	2.717 (2)	112.9
C6—H6···O2ⁱ	0.93	2.43	3.344 (2)	168.8
C8—H8···O2ⁱ	0.93	2.26	3.159 (2)	162.2

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors are grateful for the financial support of the Education Office Foundation of Zhejiang Province (project No. Y200803795).

References

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Volume 65| Part 5| May 2009| Pages o1015-o1016

doi:10.1107/S160053680901263X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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