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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028448/is6120sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028448/is6120Isup2.hkl
Contains datablock I

CCDC reference: 287607

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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 ππ 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).

Refinement top

All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å and with Uiso(H) = 1.2Ueq(C).

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
[Figure 1] Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] 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
C16H10Cl2N6OF(000) = 1520
Mr = 373.20Dx = 1.518 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 21.950 (3) ÅCell parameters from 2583 reflections
b = 9.9632 (15) Åθ = 2.3–24.0°
c = 15.538 (2) ŵ = 0.42 mm1
β = 106.028 (2)°T = 293 K
V = 3266.0 (8) Å3Column, colorless
Z = 80.40 × 0.23 × 0.12 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3199 independent reflections
Radiation source: fine-focus sealed tube2500 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 1.9°
ω scansh = 2722
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1112
Tmin = 0.851, Tmax = 0.952l = 1819
8949 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0519P)2 + 3.9871P]
where P = (Fo2 + 2Fc2)/3
3199 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C16H10Cl2N6OV = 3266.0 (8) Å3
Mr = 373.20Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.950 (3) ŵ = 0.42 mm1
b = 9.9632 (15) ÅT = 293 K
c = 15.538 (2) Å0.40 × 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)
Tmin = 0.851, Tmax = 0.952Rint = 0.023
8949 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.03Δρmax = 0.42 e Å3
3199 reflectionsΔρmin = 0.36 e Å3
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
xyzUiso*/Ueq
Cl10.33292 (6)1.12155 (9)0.06212 (8)0.1071 (4)
Cl20.41646 (5)0.62594 (10)0.15957 (5)0.0851 (3)
O10.33974 (11)0.44636 (19)0.01778 (13)0.0697 (6)
N10.33146 (9)0.37073 (19)0.15203 (13)0.0437 (5)
N20.27958 (10)0.3143 (2)0.20955 (15)0.0549 (6)
N30.29213 (11)0.1899 (2)0.22229 (15)0.0580 (6)
N40.43557 (10)0.6012 (2)0.11022 (14)0.0522 (5)
N50.37503 (9)0.58826 (19)0.16354 (13)0.0417 (5)
N60.42355 (11)0.7076 (2)0.24165 (16)0.0619 (6)
C10.30189 (12)0.7756 (3)0.06665 (17)0.0490 (6)
H1A0.27950.74630.12340.059*
C20.29920 (14)0.9090 (3)0.0458 (2)0.0577 (7)
H2B0.27450.96860.08700.069*
C30.33350 (15)0.9524 (3)0.0369 (2)0.0620 (8)
C40.36904 (15)0.8649 (3)0.09930 (19)0.0644 (8)
H4B0.39220.89640.15510.077*
C50.37023 (13)0.7298 (3)0.07887 (17)0.0538 (7)
C60.33690 (11)0.6825 (2)0.00607 (16)0.0443 (6)
C70.33672 (12)0.5395 (2)0.03232 (17)0.0458 (6)
C80.32881 (11)0.5123 (2)0.13298 (16)0.0426 (5)
H8A0.28670.54470.16610.051*
C90.37935 (11)0.2787 (2)0.12804 (16)0.0435 (6)
C100.44156 (12)0.2832 (3)0.07300 (19)0.0545 (7)
H10A0.45870.35990.04140.065*
C110.47549 (14)0.1673 (3)0.0688 (2)0.0654 (8)
H11A0.51700.16530.03270.079*
C120.45038 (16)0.0513 (3)0.1167 (2)0.0688 (8)
H12A0.47600.02400.11260.083*
C130.38949 (15)0.0463 (3)0.16895 (19)0.0599 (7)
H13A0.37260.03120.19980.072*
C140.35348 (12)0.1635 (2)0.17407 (16)0.0472 (6)
C150.46185 (13)0.6725 (3)0.16102 (19)0.0536 (6)
H15A0.50430.69740.14260.064*
C160.36978 (13)0.6528 (3)0.24046 (17)0.0535 (7)
H16A0.33270.65810.28710.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1652 (11)0.0523 (5)0.1232 (8)0.0194 (6)0.0723 (8)0.0329 (5)
Cl20.0982 (7)0.0934 (7)0.0518 (4)0.0064 (5)0.0007 (4)0.0107 (4)
O10.1069 (17)0.0473 (11)0.0589 (12)0.0018 (11)0.0294 (12)0.0071 (9)
N10.0414 (11)0.0394 (11)0.0454 (11)0.0032 (8)0.0037 (9)0.0055 (9)
N20.0473 (12)0.0503 (13)0.0589 (14)0.0074 (10)0.0009 (10)0.0073 (11)
N30.0624 (15)0.0444 (13)0.0594 (14)0.0104 (11)0.0038 (11)0.0100 (11)
N40.0451 (12)0.0580 (14)0.0507 (12)0.0076 (10)0.0084 (10)0.0001 (10)
N50.0439 (11)0.0394 (11)0.0401 (11)0.0003 (8)0.0084 (9)0.0020 (8)
N60.0626 (15)0.0653 (16)0.0623 (15)0.0015 (12)0.0249 (12)0.0126 (12)
C10.0562 (15)0.0477 (15)0.0457 (14)0.0002 (12)0.0184 (12)0.0016 (11)
C20.0726 (18)0.0446 (15)0.0649 (18)0.0023 (13)0.0339 (15)0.0022 (13)
C30.084 (2)0.0453 (16)0.0699 (19)0.0127 (14)0.0427 (17)0.0137 (14)
C40.080 (2)0.071 (2)0.0485 (16)0.0255 (16)0.0277 (15)0.0211 (15)
C50.0584 (16)0.0615 (17)0.0443 (14)0.0114 (13)0.0186 (12)0.0027 (12)
C60.0485 (14)0.0464 (14)0.0418 (13)0.0056 (11)0.0190 (11)0.0022 (11)
C70.0472 (14)0.0427 (14)0.0475 (14)0.0021 (11)0.0130 (11)0.0013 (11)
C80.0419 (13)0.0382 (13)0.0456 (13)0.0006 (10)0.0085 (10)0.0023 (10)
C90.0506 (14)0.0375 (13)0.0420 (13)0.0010 (10)0.0125 (11)0.0020 (10)
C100.0482 (15)0.0480 (15)0.0604 (16)0.0026 (12)0.0036 (12)0.0056 (12)
C110.0539 (16)0.0592 (18)0.079 (2)0.0084 (14)0.0111 (15)0.0166 (16)
C120.078 (2)0.0495 (17)0.083 (2)0.0196 (15)0.0289 (18)0.0130 (15)
C130.084 (2)0.0391 (14)0.0596 (17)0.0002 (14)0.0257 (16)0.0006 (12)
C140.0569 (15)0.0412 (13)0.0423 (13)0.0050 (11)0.0118 (12)0.0004 (10)
C150.0496 (15)0.0519 (15)0.0611 (16)0.0043 (12)0.0185 (13)0.0022 (13)
C160.0542 (16)0.0575 (16)0.0468 (14)0.0065 (13)0.0106 (12)0.0066 (12)
Geometric parameters (Å, º) top
Cl1—C31.731 (3)C3—C41.375 (4)
Cl2—C51.723 (3)C4—C51.385 (4)
O1—C71.201 (3)C4—H4B0.9300
N1—N21.360 (3)C5—C61.402 (3)
N1—C91.367 (3)C6—C71.482 (3)
N1—C81.445 (3)C7—C81.549 (3)
N2—N31.296 (3)C8—H8A0.9800
N3—C141.374 (3)C9—C141.388 (3)
N4—C151.308 (3)C9—C101.398 (3)
N4—N51.364 (3)C10—C111.366 (4)
N5—C161.334 (3)C10—H10A0.9300
N5—C81.447 (3)C11—C121.402 (4)
N6—C161.305 (3)C11—H11A0.9300
N6—C151.348 (4)C12—C131.360 (4)
C1—C21.373 (4)C12—H12A0.9300
C1—C61.392 (3)C13—C141.400 (4)
C1—H1A0.9300C13—H13A0.9300
C2—C31.368 (4)C15—H15A0.9300
C2—H2B0.9300C16—H16A0.9300
N2—N1—C9110.06 (19)N1—C8—N5111.83 (19)
N2—N1—C8117.67 (19)N1—C8—C7112.21 (19)
C9—N1—C8132.07 (19)N5—C8—C7110.26 (18)
N3—N2—N1108.7 (2)N1—C8—H8A107.4
N2—N3—C14108.5 (2)N5—C8—H8A107.4
C15—N4—N5101.7 (2)C7—C8—H8A107.4
C16—N5—N4109.1 (2)N1—C9—C14103.9 (2)
C16—N5—C8130.6 (2)N1—C9—C10133.9 (2)
N4—N5—C8120.26 (19)C14—C9—C10122.2 (2)
C16—N6—C15102.3 (2)C11—C10—C9115.5 (3)
C2—C1—C6122.5 (3)C11—C10—H10A122.3
C2—C1—H1A118.8C9—C10—H10A122.3
C6—C1—H1A118.8C10—C11—C12122.8 (3)
C3—C2—C1118.7 (3)C10—C11—H11A118.6
C3—C2—H2B120.7C12—C11—H11A118.6
C1—C2—H2B120.7C13—C12—C11121.6 (3)
C2—C3—C4121.3 (3)C13—C12—H12A119.2
C2—C3—Cl1118.9 (3)C11—C12—H12A119.2
C4—C3—Cl1119.8 (2)C12—C13—C14116.7 (3)
C3—C4—C5119.9 (3)C12—C13—H13A121.6
C3—C4—H4B120.1C14—C13—H13A121.6
C5—C4—H4B120.1N3—C14—C9108.8 (2)
C4—C5—C6120.3 (3)N3—C14—C13130.1 (2)
C4—C5—Cl2117.5 (2)C9—C14—C13121.1 (2)
C6—C5—Cl2122.2 (2)N4—C15—N6115.8 (2)
C1—C6—C5117.4 (2)N4—C15—H15A122.1
C1—C6—C7119.7 (2)N6—C15—H15A122.1
C5—C6—C7122.9 (2)N6—C16—N5111.1 (2)
O1—C7—C6124.7 (2)N6—C16—H16A124.5
O1—C7—C8119.3 (2)N5—C16—H16A124.5
C6—C7—C8115.9 (2)
C9—N1—N2—N30.8 (3)C16—N5—C8—C7140.9 (3)
C8—N1—N2—N3176.3 (2)N4—N5—C8—C739.7 (3)
N1—N2—N3—C141.1 (3)O1—C7—C8—N14.9 (3)
C15—N4—N5—C160.6 (3)C6—C7—C8—N1177.9 (2)
C15—N4—N5—C8178.9 (2)O1—C7—C8—N5130.3 (2)
C6—C1—C2—C31.7 (4)C6—C7—C8—N552.5 (3)
C1—C2—C3—C41.4 (4)N2—N1—C9—C140.1 (3)
C1—C2—C3—Cl1177.4 (2)C8—N1—C9—C14174.8 (2)
C2—C3—C4—C50.3 (4)N2—N1—C9—C10179.1 (3)
Cl1—C3—C4—C5179.2 (2)C8—N1—C9—C104.4 (5)
C3—C4—C5—C62.0 (4)N1—C9—C10—C11178.0 (3)
C3—C4—C5—Cl2179.3 (2)C14—C9—C10—C111.1 (4)
C2—C1—C6—C50.1 (4)C9—C10—C11—C120.5 (4)
C2—C1—C6—C7178.8 (2)C10—C11—C12—C131.7 (5)
C4—C5—C6—C11.7 (4)C11—C12—C13—C141.3 (4)
Cl2—C5—C6—C1178.90 (19)N2—N3—C14—C91.0 (3)
C4—C5—C6—C7179.5 (2)N2—N3—C14—C13177.1 (3)
Cl2—C5—C6—C72.3 (4)N1—C9—C14—N30.5 (3)
C1—C6—C7—O1146.0 (3)C10—C9—C14—N3179.8 (2)
C5—C6—C7—O132.8 (4)N1—C9—C14—C13177.8 (2)
C1—C6—C7—C831.0 (3)C10—C9—C14—C131.5 (4)
C5—C6—C7—C8150.3 (2)C12—C13—C14—N3178.2 (3)
N2—N1—C8—N5116.3 (2)C12—C13—C14—C90.3 (4)
C9—N1—C8—N558.0 (3)N5—N4—C15—N60.7 (3)
N2—N1—C8—C7119.2 (2)C16—N6—C15—N40.5 (3)
C9—N1—C8—C766.5 (3)C15—N6—C16—N50.1 (3)
C16—N5—C8—N193.5 (3)N4—N5—C16—N60.3 (3)
N4—N5—C8—N185.8 (2)C8—N5—C16—N6179.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···N3i0.932.543.465 (3)172
C8—H8A···N3i0.982.543.455 (3)156
Symmetry code: (i) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC16H10Cl2N6O
Mr373.20
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)21.950 (3), 9.9632 (15), 15.538 (2)
β (°) 106.028 (2)
V3)3266.0 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.40 × 0.23 × 0.12
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.851, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections
8949, 3199, 2500
Rint0.023
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.130, 1.03
No. of reflections3199
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—C31.731 (3)N1—C81.445 (3)
Cl2—C51.723 (3)N5—C81.447 (3)
O1—C71.201 (3)C7—C81.549 (3)
N1—C8—N5111.83 (19)N5—C8—C7110.26 (18)
N1—C8—C7112.21 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···N3i0.932.543.465 (3)172
C8—H8A···N3i0.982.543.455 (3)156
Symmetry code: (i) x+1/2, y+1/2, z1/2.
 

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