2-(1H-Benzotriazol-1-yl)-1-(2,4-dichloro­phen­yl)-2-(1H-1,2,4-triazol-1-­yl)ethanone

Wan, J.; Li, C.-L.; Li, X.-M.; Zhang, S.-S.; Ouyang, P.-K.

doi:10.1107/S1600536805028448

2-(1H-Benzotriazol-1-yl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

J. Wan, C.-L. Li, X.-M. Li, S.-S. Zhang and P.-K. Ouyang

In the title compound, C₁₆H₁₀Cl₂N₆O, molecules are linked into ribbons along the b axis by C—H

N intermolecular hydrogen bonds. The packing is further stabilized by a π–π interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028448/is6120sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028448/is6120Isup2.hkl Contains datablock I

CCDC reference: 287607

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.053
wR factor = 0.130
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Triazole derivatives exhibit growth-inhibiting activites against some microorganisms (Xu et al., 2002). In order to search for new triazole compounds with higher bioactivity, the title compound, (I), including triazole and benzotriazole, was synthesized.

The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987) and comparable to those reported in the related compound 2-(1H-1,2,3-benzotriazol-1-yl)-1-(4-methylphenyl)-2- (1H-1,2,4-triazol-1-yl)ethanone (Wan et al., 2005). The benzotriazole group is essentially planar, with a dihedral angle of 1.9 (1)° between the benzene and triazole rings. The mean plane of the benzotriazole group makes dihedral angles of 74.3 (1) and 33.9 (1)° with the other triazole (N4/N5/C16/N6/C15) ring and the benzene (C1–C6) ring, respectively. The dihedral angle between the planes of the latter two aromatic rings is 69.9 (1)°. In the crystal structure, molecules are linked into ribbons by intermolecular C—H···N hydrogen bonds (Fig. 2 and Table 2). The packing is further stabilized by a π–π interaction between the benzene (C1–C6) rings, the distance between the centroids [Cg···Cg(1/2 − x, 3/2 − y, −z)] being 3.883 (2) Å.

Experimental top

The title compound was prepared according to the method of Wan et al. (2005).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view down the c axis. Hydrogen bonds are indicated by dashed lines.

2-(1H-Benzotriazol-1-yl))-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1- yl)ethanone top

Crystal data top

C₁₆H₁₀Cl₂N₆O	F(000) = 1520
M_r = 373.20	D_x = 1.518 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.950 (3) Å	Cell parameters from 2583 reflections
b = 9.9632 (15) Å	θ = 2.3–24.0°
c = 15.538 (2) Å	µ = 0.42 mm⁻¹
β = 106.028 (2)°	T = 293 K
V = 3266.0 (8) Å³	Column, colorless
Z = 8	0.40 × 0.23 × 0.12 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3199 independent reflections
Radiation source: fine-focus sealed tube	2500 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 1.9°
ω scans	h = −27→22
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→12
T_min = 0.851, T_max = 0.952	l = −18→19
8949 measured reflections

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0519P)² + 3.9871P] where P = (F_o² + 2F_c²)/3
3199 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₆H₁₀Cl₂N₆O	V = 3266.0 (8) Å³
M_r = 373.20	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.950 (3) Å	µ = 0.42 mm⁻¹
b = 9.9632 (15) Å	T = 293 K
c = 15.538 (2) Å	0.40 × 0.23 × 0.12 mm
β = 106.028 (2)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3199 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2500 reflections with I > 2σ(I)
T_min = 0.851, T_max = 0.952	R_int = 0.023
8949 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
3199 reflections	Δρ_min = −0.36 e Å⁻³
226 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
Cl1	0.33292 (6)	1.12155 (9)	0.06212 (8)	0.1071 (4)
Cl2	0.41646 (5)	0.62594 (10)	0.15957 (5)	0.0851 (3)
O1	0.33974 (11)	0.44636 (19)	0.01778 (13)	0.0697 (6)
N1	0.33146 (9)	0.37073 (19)	−0.15203 (13)	0.0437 (5)
N2	0.27958 (10)	0.3143 (2)	−0.20955 (15)	0.0549 (6)
N3	0.29213 (11)	0.1899 (2)	−0.22229 (15)	0.0580 (6)
N4	0.43557 (10)	0.6012 (2)	−0.11022 (14)	0.0522 (5)
N5	0.37503 (9)	0.58826 (19)	−0.16354 (13)	0.0417 (5)
N6	0.42355 (11)	0.7076 (2)	−0.24165 (16)	0.0619 (6)
C1	0.30189 (12)	0.7756 (3)	−0.06665 (17)	0.0490 (6)
H1A	0.2795	0.7463	−0.1234	0.059*
C2	0.29920 (14)	0.9090 (3)	−0.0458 (2)	0.0577 (7)
H2B	0.2745	0.9686	−0.0870	0.069*
C3	0.33350 (15)	0.9524 (3)	0.0369 (2)	0.0620 (8)
C4	0.36904 (15)	0.8649 (3)	0.09930 (19)	0.0644 (8)
H4B	0.3922	0.8964	0.1551	0.077*
C5	0.37023 (13)	0.7298 (3)	0.07887 (17)	0.0538 (7)
C6	0.33690 (11)	0.6825 (2)	−0.00607 (16)	0.0443 (6)
C7	0.33672 (12)	0.5395 (2)	−0.03232 (17)	0.0458 (6)
C8	0.32881 (11)	0.5123 (2)	−0.13298 (16)	0.0426 (5)
H8A	0.2867	0.5447	−0.1661	0.051*
C9	0.37935 (11)	0.2787 (2)	−0.12804 (16)	0.0435 (6)
C10	0.44156 (12)	0.2832 (3)	−0.07300 (19)	0.0545 (7)
H10A	0.4587	0.3599	−0.0414	0.065*
C11	0.47549 (14)	0.1673 (3)	−0.0688 (2)	0.0654 (8)
H11A	0.5170	0.1653	−0.0327	0.079*
C12	0.45038 (16)	0.0513 (3)	−0.1167 (2)	0.0688 (8)
H12A	0.4760	−0.0240	−0.1126	0.083*
C13	0.38949 (15)	0.0463 (3)	−0.16895 (19)	0.0599 (7)
H13A	0.3726	−0.0312	−0.1998	0.072*
C14	0.35348 (12)	0.1635 (2)	−0.17407 (16)	0.0472 (6)
C15	0.46185 (13)	0.6725 (3)	−0.16102 (19)	0.0536 (6)
H15A	0.5043	0.6974	−0.1426	0.064*
C16	0.36978 (13)	0.6528 (3)	−0.24046 (17)	0.0535 (7)
H16A	0.3327	0.6581	−0.2871	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1652 (11)	0.0523 (5)	0.1232 (8)	−0.0194 (6)	0.0723 (8)	−0.0329 (5)
Cl2	0.0982 (7)	0.0934 (7)	0.0518 (4)	−0.0064 (5)	0.0007 (4)	0.0107 (4)
O1	0.1069 (17)	0.0473 (11)	0.0589 (12)	−0.0018 (11)	0.0294 (12)	0.0071 (9)
N1	0.0414 (11)	0.0394 (11)	0.0454 (11)	−0.0032 (8)	0.0037 (9)	−0.0055 (9)
N2	0.0473 (12)	0.0503 (13)	0.0589 (14)	−0.0074 (10)	0.0009 (10)	−0.0073 (11)
N3	0.0624 (15)	0.0444 (13)	0.0594 (14)	−0.0104 (11)	0.0038 (11)	−0.0100 (11)
N4	0.0451 (12)	0.0580 (14)	0.0507 (12)	−0.0076 (10)	0.0084 (10)	0.0001 (10)
N5	0.0439 (11)	0.0394 (11)	0.0401 (11)	0.0003 (8)	0.0084 (9)	−0.0020 (8)
N6	0.0626 (15)	0.0653 (16)	0.0623 (15)	0.0015 (12)	0.0249 (12)	0.0126 (12)
C1	0.0562 (15)	0.0477 (15)	0.0457 (14)	−0.0002 (12)	0.0184 (12)	−0.0016 (11)
C2	0.0726 (18)	0.0446 (15)	0.0649 (18)	0.0023 (13)	0.0339 (15)	0.0022 (13)
C3	0.084 (2)	0.0453 (16)	0.0699 (19)	−0.0127 (14)	0.0427 (17)	−0.0137 (14)
C4	0.080 (2)	0.071 (2)	0.0485 (16)	−0.0255 (16)	0.0277 (15)	−0.0211 (15)
C5	0.0584 (16)	0.0615 (17)	0.0443 (14)	−0.0114 (13)	0.0186 (12)	−0.0027 (12)
C6	0.0485 (14)	0.0464 (14)	0.0418 (13)	−0.0056 (11)	0.0190 (11)	−0.0022 (11)
C7	0.0472 (14)	0.0427 (14)	0.0475 (14)	−0.0021 (11)	0.0130 (11)	0.0013 (11)
C8	0.0419 (13)	0.0382 (13)	0.0456 (13)	−0.0006 (10)	0.0085 (10)	−0.0023 (10)
C9	0.0506 (14)	0.0375 (13)	0.0420 (13)	−0.0010 (10)	0.0125 (11)	0.0020 (10)
C10	0.0482 (15)	0.0480 (15)	0.0604 (16)	−0.0026 (12)	0.0036 (12)	0.0056 (12)
C11	0.0539 (16)	0.0592 (18)	0.079 (2)	0.0084 (14)	0.0111 (15)	0.0166 (16)
C12	0.078 (2)	0.0495 (17)	0.083 (2)	0.0196 (15)	0.0289 (18)	0.0130 (15)
C13	0.084 (2)	0.0391 (14)	0.0596 (17)	0.0002 (14)	0.0257 (16)	−0.0006 (12)
C14	0.0569 (15)	0.0412 (13)	0.0423 (13)	−0.0050 (11)	0.0118 (12)	−0.0004 (10)
C15	0.0496 (15)	0.0519 (15)	0.0611 (16)	−0.0043 (12)	0.0185 (13)	−0.0022 (13)
C16	0.0542 (16)	0.0575 (16)	0.0468 (14)	0.0065 (13)	0.0106 (12)	0.0066 (12)

Geometric parameters (Å, º) top

Cl1—C3	1.731 (3)	C3—C4	1.375 (4)
Cl2—C5	1.723 (3)	C4—C5	1.385 (4)
O1—C7	1.201 (3)	C4—H4B	0.9300
N1—N2	1.360 (3)	C5—C6	1.402 (3)
N1—C9	1.367 (3)	C6—C7	1.482 (3)
N1—C8	1.445 (3)	C7—C8	1.549 (3)
N2—N3	1.296 (3)	C8—H8A	0.9800
N3—C14	1.374 (3)	C9—C14	1.388 (3)
N4—C15	1.308 (3)	C9—C10	1.398 (3)
N4—N5	1.364 (3)	C10—C11	1.366 (4)
N5—C16	1.334 (3)	C10—H10A	0.9300
N5—C8	1.447 (3)	C11—C12	1.402 (4)
N6—C16	1.305 (3)	C11—H11A	0.9300
N6—C15	1.348 (4)	C12—C13	1.360 (4)
C1—C2	1.373 (4)	C12—H12A	0.9300
C1—C6	1.392 (3)	C13—C14	1.400 (4)
C1—H1A	0.9300	C13—H13A	0.9300
C2—C3	1.368 (4)	C15—H15A	0.9300
C2—H2B	0.9300	C16—H16A	0.9300

N2—N1—C9	110.06 (19)	N1—C8—N5	111.83 (19)
N2—N1—C8	117.67 (19)	N1—C8—C7	112.21 (19)
C9—N1—C8	132.07 (19)	N5—C8—C7	110.26 (18)
N3—N2—N1	108.7 (2)	N1—C8—H8A	107.4
N2—N3—C14	108.5 (2)	N5—C8—H8A	107.4
C15—N4—N5	101.7 (2)	C7—C8—H8A	107.4
C16—N5—N4	109.1 (2)	N1—C9—C14	103.9 (2)
C16—N5—C8	130.6 (2)	N1—C9—C10	133.9 (2)
N4—N5—C8	120.26 (19)	C14—C9—C10	122.2 (2)
C16—N6—C15	102.3 (2)	C11—C10—C9	115.5 (3)
C2—C1—C6	122.5 (3)	C11—C10—H10A	122.3
C2—C1—H1A	118.8	C9—C10—H10A	122.3
C6—C1—H1A	118.8	C10—C11—C12	122.8 (3)
C3—C2—C1	118.7 (3)	C10—C11—H11A	118.6
C3—C2—H2B	120.7	C12—C11—H11A	118.6
C1—C2—H2B	120.7	C13—C12—C11	121.6 (3)
C2—C3—C4	121.3 (3)	C13—C12—H12A	119.2
C2—C3—Cl1	118.9 (3)	C11—C12—H12A	119.2
C4—C3—Cl1	119.8 (2)	C12—C13—C14	116.7 (3)
C3—C4—C5	119.9 (3)	C12—C13—H13A	121.6
C3—C4—H4B	120.1	C14—C13—H13A	121.6
C5—C4—H4B	120.1	N3—C14—C9	108.8 (2)
C4—C5—C6	120.3 (3)	N3—C14—C13	130.1 (2)
C4—C5—Cl2	117.5 (2)	C9—C14—C13	121.1 (2)
C6—C5—Cl2	122.2 (2)	N4—C15—N6	115.8 (2)
C1—C6—C5	117.4 (2)	N4—C15—H15A	122.1
C1—C6—C7	119.7 (2)	N6—C15—H15A	122.1
C5—C6—C7	122.9 (2)	N6—C16—N5	111.1 (2)
O1—C7—C6	124.7 (2)	N6—C16—H16A	124.5
O1—C7—C8	119.3 (2)	N5—C16—H16A	124.5
C6—C7—C8	115.9 (2)

C9—N1—N2—N3	0.8 (3)	C16—N5—C8—C7	−140.9 (3)
C8—N1—N2—N3	176.3 (2)	N4—N5—C8—C7	39.7 (3)
N1—N2—N3—C14	−1.1 (3)	O1—C7—C8—N1	−4.9 (3)
C15—N4—N5—C16	−0.6 (3)	C6—C7—C8—N1	177.9 (2)
C15—N4—N5—C8	178.9 (2)	O1—C7—C8—N5	−130.3 (2)
C6—C1—C2—C3	1.7 (4)	C6—C7—C8—N5	52.5 (3)
C1—C2—C3—C4	−1.4 (4)	N2—N1—C9—C14	−0.1 (3)
C1—C2—C3—Cl1	177.4 (2)	C8—N1—C9—C14	−174.8 (2)
C2—C3—C4—C5	−0.3 (4)	N2—N1—C9—C10	179.1 (3)
Cl1—C3—C4—C5	−179.2 (2)	C8—N1—C9—C10	4.4 (5)
C3—C4—C5—C6	2.0 (4)	N1—C9—C10—C11	−178.0 (3)
C3—C4—C5—Cl2	179.3 (2)	C14—C9—C10—C11	1.1 (4)
C2—C1—C6—C5	−0.1 (4)	C9—C10—C11—C12	0.5 (4)
C2—C1—C6—C7	178.8 (2)	C10—C11—C12—C13	−1.7 (5)
C4—C5—C6—C1	−1.7 (4)	C11—C12—C13—C14	1.3 (4)
Cl2—C5—C6—C1	−178.90 (19)	N2—N3—C14—C9	1.0 (3)
C4—C5—C6—C7	179.5 (2)	N2—N3—C14—C13	−177.1 (3)
Cl2—C5—C6—C7	2.3 (4)	N1—C9—C14—N3	−0.5 (3)
C1—C6—C7—O1	−146.0 (3)	C10—C9—C14—N3	−179.8 (2)
C5—C6—C7—O1	32.8 (4)	N1—C9—C14—C13	177.8 (2)
C1—C6—C7—C8	31.0 (3)	C10—C9—C14—C13	−1.5 (4)
C5—C6—C7—C8	−150.3 (2)	C12—C13—C14—N3	178.2 (3)
N2—N1—C8—N5	−116.3 (2)	C12—C13—C14—C9	0.3 (4)
C9—N1—C8—N5	58.0 (3)	N5—N4—C15—N6	0.7 (3)
N2—N1—C8—C7	119.2 (2)	C16—N6—C15—N4	−0.5 (3)
C9—N1—C8—C7	−66.5 (3)	C15—N6—C16—N5	0.1 (3)
C16—N5—C8—N1	93.5 (3)	N4—N5—C16—N6	0.3 (3)
N4—N5—C8—N1	−85.8 (2)	C8—N5—C16—N6	−179.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N3ⁱ	0.93	2.54	3.465 (3)	172
C8—H8A···N3ⁱ	0.98	2.54	3.455 (3)	156

Symmetry code: (i) −x+1/2, y+1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀Cl₂N₆O
M_r	373.20
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.950 (3), 9.9632 (15), 15.538 (2)
β (°)	106.028 (2)
V (Å³)	3266.0 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.40 × 0.23 × 0.12

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.851, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	8949, 3199, 2500
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.130, 1.03
No. of reflections	3199
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.36

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Cl1—C3	1.731 (3)	N1—C8	1.445 (3)
Cl2—C5	1.723 (3)	N5—C8	1.447 (3)
O1—C7	1.201 (3)	C7—C8	1.549 (3)

N1—C8—N5	111.83 (19)	N5—C8—C7	110.26 (18)
N1—C8—C7	112.21 (19)