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The molecule of the title compound, C11H9Cl2N3O, is nonplanar, with a dihedral angle of 80.04 (11)° between the benzene and triazole rings. The packing is stabilized by π–π inter­actions, with centroid–centroid distances of 3.724 and 3.590 Å for the triazole and benzene rings, respectively, and by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026207/at2305sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026207/at2305Isup2.hkl
Contains datablock I

CCDC reference: 654852

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.108
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.664 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G 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 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of our ongoing studies on triazole compounds, the title compound, (I), was obtained by the reaction of triazole and 1-(3,4-dichlorophenyl)-3-(dimethylamino)propan-1-one hydrochloride. We reports the crystal structure of (I) here.

All the bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The whole molecule is non-planar with a dihedral angle of 80.04 (11)° between the benzene ring (C1—C6) and triazole ring (N1—N3/C10/C11). The crystal packing is further stabilized by Van der Waals forces. The short distances Cg1···Cg1i (3.724 Å) and Cg2···Cg2ii (3.590 Å) [symmetry code: (i) 2 - x, 1 - y, 3 - z; (ii)1 - x, 1 - y, 2 - z], where Cg1 and Cg2 denote the centroids of triazole ring and benzene ring, respectively, indicate π-π interactions.

Related literature top

For related literature, see: Wan et al. (2005); Allen et al. (1987).

Experimental top

The title compound (I) was prepared according to the literature method of Wan et al. (2005). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of 5 d.

Refinement top

The H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C).

Structure description top

As part of our ongoing studies on triazole compounds, the title compound, (I), was obtained by the reaction of triazole and 1-(3,4-dichlorophenyl)-3-(dimethylamino)propan-1-one hydrochloride. We reports the crystal structure of (I) here.

All the bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The whole molecule is non-planar with a dihedral angle of 80.04 (11)° between the benzene ring (C1—C6) and triazole ring (N1—N3/C10/C11). The crystal packing is further stabilized by Van der Waals forces. The short distances Cg1···Cg1i (3.724 Å) and Cg2···Cg2ii (3.590 Å) [symmetry code: (i) 2 - x, 1 - y, 3 - z; (ii)1 - x, 1 - y, 2 - z], where Cg1 and Cg2 denote the centroids of triazole ring and benzene ring, respectively, indicate π-π interactions.

For related literature, see: Wan et al. (2005); Allen et al. (1987).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. Packing diagram of (I) viewed down the a axis.
1-(3,4-Dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one top
Crystal data top
C11H9Cl2N3OZ = 2
Mr = 270.11F(000) = 276
Triclinic, P1Dx = 1.573 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8296 (10) ÅCell parameters from 1835 reflections
b = 7.1403 (11) Åθ = 3.1–26.0°
c = 12.3933 (19) ŵ = 0.55 mm1
α = 80.830 (2)°T = 293 K
β = 78.724 (2)°Plate, colourless
γ = 75.612 (2)°0.27 × 0.27 × 0.07 mm
V = 570.19 (15) Å3
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2194 independent reflections
Radiation source: fine-focus sealed tube1955 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.009
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 1.7°
ω scansh = 84
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 88
Tmin = 0.865, Tmax = 0.962l = 1515
3183 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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 0.66 w = 1/[σ2(Fo2) + (0.1029P)2 + 0.463P]
where P = (Fo2 + 2Fc2)/3
2194 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C11H9Cl2N3Oγ = 75.612 (2)°
Mr = 270.11V = 570.19 (15) Å3
Triclinic, P1Z = 2
a = 6.8296 (10) ÅMo Kα radiation
b = 7.1403 (11) ŵ = 0.55 mm1
c = 12.3933 (19) ÅT = 293 K
α = 80.830 (2)°0.27 × 0.27 × 0.07 mm
β = 78.724 (2)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2194 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1955 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.962Rint = 0.009
3183 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 0.66Δρmax = 0.20 e Å3
2194 reflectionsΔρmin = 0.22 e Å3
154 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
Cl10.21802 (8)0.95267 (7)0.80256 (4)0.05716 (19)
Cl20.70100 (8)0.87272 (8)0.76018 (4)0.05845 (19)
C60.5728 (3)0.6771 (2)1.08034 (13)0.0355 (4)
O10.8822 (2)0.5501 (2)1.15061 (11)0.0532 (4)
N10.8075 (2)0.6065 (2)1.40105 (12)0.0443 (4)
C50.3598 (3)0.7133 (2)1.09772 (15)0.0406 (4)
H5A0.28920.68151.16770.049*
C10.6769 (3)0.7250 (2)0.97532 (14)0.0382 (4)
H1A0.81930.69960.96260.046*
C40.2519 (3)0.7961 (3)1.01167 (16)0.0437 (4)
H4A0.10980.81791.02370.052*
C70.6964 (3)0.5855 (2)1.17056 (14)0.0377 (4)
C80.5837 (3)0.5375 (3)1.28599 (14)0.0403 (4)
H8A0.50450.44331.28330.048*
H8B0.48850.65461.30960.048*
C30.3558 (3)0.8462 (2)0.90829 (15)0.0396 (4)
C20.5691 (3)0.8107 (2)0.88940 (14)0.0394 (4)
C90.7250 (3)0.4561 (3)1.37097 (15)0.0438 (4)
H9A0.64990.39701.43680.053*
H9B0.83710.35541.34110.053*
N20.6857 (3)0.7499 (3)1.45984 (14)0.0580 (5)
C120.9975 (3)0.6333 (4)1.37805 (17)0.0594 (6)
H12A1.10730.55211.33890.071*
N31.0108 (4)0.7888 (3)1.41752 (17)0.0744 (6)
C130.8161 (5)0.8543 (4)1.46695 (18)0.0689 (7)
H13A0.77680.96531.50340.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0636 (3)0.0552 (3)0.0515 (3)0.0020 (2)0.0247 (2)0.0020 (2)
Cl20.0628 (3)0.0730 (4)0.0343 (3)0.0149 (3)0.0007 (2)0.0001 (2)
C60.0395 (9)0.0339 (8)0.0350 (8)0.0110 (7)0.0055 (7)0.0059 (6)
O10.0388 (7)0.0748 (9)0.0416 (7)0.0087 (6)0.0049 (5)0.0029 (6)
N10.0470 (8)0.0567 (9)0.0315 (7)0.0195 (7)0.0074 (6)0.0019 (6)
C50.0390 (9)0.0425 (9)0.0395 (9)0.0127 (7)0.0030 (7)0.0014 (7)
C10.0382 (9)0.0403 (8)0.0374 (9)0.0108 (7)0.0046 (7)0.0076 (7)
C40.0384 (9)0.0426 (9)0.0501 (10)0.0096 (7)0.0084 (8)0.0033 (7)
C70.0395 (9)0.0397 (8)0.0352 (9)0.0104 (7)0.0056 (7)0.0069 (7)
C80.0402 (9)0.0454 (9)0.0368 (9)0.0138 (7)0.0048 (7)0.0040 (7)
C30.0465 (9)0.0323 (8)0.0418 (9)0.0062 (7)0.0140 (7)0.0057 (6)
C20.0488 (10)0.0364 (8)0.0339 (8)0.0128 (7)0.0036 (7)0.0062 (6)
C90.0467 (10)0.0476 (10)0.0368 (9)0.0132 (8)0.0067 (7)0.0001 (7)
N20.0692 (11)0.0622 (10)0.0461 (9)0.0237 (9)0.0020 (8)0.0116 (8)
C120.0520 (11)0.0837 (15)0.0460 (11)0.0293 (11)0.0127 (9)0.0109 (10)
N30.0877 (15)0.0959 (15)0.0591 (12)0.0577 (13)0.0323 (11)0.0180 (11)
C130.109 (2)0.0717 (14)0.0412 (11)0.0455 (14)0.0217 (12)0.0023 (10)
Geometric parameters (Å, º) top
Cl1—C31.7291 (17)C4—H4A0.9300
Cl2—C21.7262 (17)C7—C81.517 (2)
C6—C51.392 (2)C8—C91.517 (3)
C6—C11.391 (2)C8—H8A0.9700
C6—C71.501 (2)C8—H8B0.9700
O1—C71.214 (2)C3—C21.394 (3)
N1—C121.328 (3)C9—H9A0.9700
N1—N21.359 (2)C9—H9B0.9700
N1—C91.456 (2)N2—C131.319 (3)
C5—C41.385 (3)C12—N31.312 (3)
C5—H5A0.9300C12—H12A0.9300
C1—C21.387 (2)N3—C131.352 (4)
C1—H1A0.9300C13—H13A0.9300
C4—C31.377 (3)
C5—C6—C1119.26 (16)C9—C8—H8B108.9
C5—C6—C7122.57 (15)H8A—C8—H8B107.7
C1—C6—C7118.17 (15)C4—C3—C2120.29 (16)
C12—N1—N2109.21 (18)C4—C3—Cl1119.09 (14)
C12—N1—C9129.46 (19)C2—C3—Cl1120.62 (14)
N2—N1—C9121.32 (15)C1—C2—C3119.74 (16)
C6—C5—C4120.62 (16)C1—C2—Cl2119.54 (14)
C6—C5—H5A119.7C3—C2—Cl2120.72 (14)
C4—C5—H5A119.7N1—C9—C8111.80 (15)
C2—C1—C6120.24 (16)N1—C9—H9A109.3
C2—C1—H1A119.9C8—C9—H9A109.3
C6—C1—H1A119.9N1—C9—H9B109.3
C3—C4—C5119.83 (17)C8—C9—H9B109.3
C3—C4—H4A120.1H9A—C9—H9B107.9
C5—C4—H4A120.1C13—N2—N1102.01 (19)
O1—C7—C6120.27 (15)N1—C12—N3111.4 (2)
O1—C7—C8121.24 (15)N1—C12—H12A124.3
C6—C7—C8118.48 (14)N3—C12—H12A124.3
C7—C8—C9113.41 (15)C12—N3—C13102.06 (19)
C7—C8—H8A108.9N2—C13—N3115.3 (2)
C9—C8—H8A108.9N2—C13—H13A122.4
C7—C8—H8B108.9N3—C13—H13A122.4
C1—C6—C5—C40.0 (2)C4—C3—C2—C10.1 (2)
C7—C6—C5—C4179.28 (15)Cl1—C3—C2—C1179.96 (12)
C5—C6—C1—C21.0 (2)C4—C3—C2—Cl2179.98 (13)
C7—C6—C1—C2179.72 (14)Cl1—C3—C2—Cl20.1 (2)
C6—C5—C4—C31.0 (3)C12—N1—C9—C8110.1 (2)
C5—C6—C7—O1177.26 (16)N2—N1—C9—C868.8 (2)
C1—C6—C7—O12.0 (2)C7—C8—C9—N173.91 (19)
C5—C6—C7—C82.3 (2)C12—N1—N2—C130.3 (2)
C1—C6—C7—C8178.48 (14)C9—N1—N2—C13178.74 (16)
O1—C7—C8—C93.7 (2)N2—N1—C12—N30.5 (2)
C6—C7—C8—C9176.79 (14)C9—N1—C12—N3178.46 (17)
C5—C4—C3—C21.1 (3)N1—C12—N3—C130.4 (2)
C5—C4—C3—Cl1179.07 (13)N1—N2—C13—N30.1 (2)
C6—C1—C2—C30.9 (2)C12—N3—C13—N20.2 (3)
C6—C1—C2—Cl2178.97 (12)

Experimental details

Crystal data
Chemical formulaC11H9Cl2N3O
Mr270.11
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.8296 (10), 7.1403 (11), 12.3933 (19)
α, β, γ (°)80.830 (2), 78.724 (2), 75.612 (2)
V3)570.19 (15)
Z2
Radiation typeMo Kα
µ (mm1)0.55
Crystal size (mm)0.27 × 0.27 × 0.07
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.865, 0.962
No. of measured, independent and
observed [I > 2σ(I)] reflections
3183, 2194, 1955
Rint0.009
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.108, 0.66
No. of reflections2194
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.22

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

 

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