Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026207/at2305sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026207/at2305Isup2.hkl |
CCDC reference: 654852
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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).
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).
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).
Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme. | |
Fig. 2. Packing diagram of (I) viewed down the a axis. |
C11H9Cl2N3O | Z = 2 |
Mr = 270.11 | F(000) = 276 |
Triclinic, P1 | Dx = 1.573 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8296 (10) Å | Cell parameters from 1835 reflections |
b = 7.1403 (11) Å | θ = 3.1–26.0° |
c = 12.3933 (19) Å | µ = 0.55 mm−1 |
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 |
Siemens SMART 1000 CCD area-detector diffractometer | 2194 independent reflections |
Radiation source: fine-focus sealed tube | 1955 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.009 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −8→4 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −8→8 |
Tmin = 0.865, Tmax = 0.962 | l = −15→15 |
3183 measured reflections |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C11H9Cl2N3O | γ = 75.612 (2)° |
Mr = 270.11 | V = 570.19 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.8296 (10) Å | Mo Kα radiation |
b = 7.1403 (11) Å | µ = 0.55 mm−1 |
c = 12.3933 (19) Å | T = 293 K |
α = 80.830 (2)° | 0.27 × 0.27 × 0.07 mm |
β = 78.724 (2)° |
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 = 0.962 | Rint = 0.009 |
3183 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 0.66 | Δρmax = 0.20 e Å−3 |
2194 reflections | Δρmin = −0.22 e Å−3 |
154 parameters |
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 | ||
Cl1 | 0.21802 (8) | 0.95267 (7) | 0.80256 (4) | 0.05716 (19) | |
Cl2 | 0.70100 (8) | 0.87272 (8) | 0.76018 (4) | 0.05845 (19) | |
C6 | 0.5728 (3) | 0.6771 (2) | 1.08034 (13) | 0.0355 (4) | |
O1 | 0.8822 (2) | 0.5501 (2) | 1.15061 (11) | 0.0532 (4) | |
N1 | 0.8075 (2) | 0.6065 (2) | 1.40105 (12) | 0.0443 (4) | |
C5 | 0.3598 (3) | 0.7133 (2) | 1.09772 (15) | 0.0406 (4) | |
H5A | 0.2892 | 0.6815 | 1.1677 | 0.049* | |
C1 | 0.6769 (3) | 0.7250 (2) | 0.97532 (14) | 0.0382 (4) | |
H1A | 0.8193 | 0.6996 | 0.9626 | 0.046* | |
C4 | 0.2519 (3) | 0.7961 (3) | 1.01167 (16) | 0.0437 (4) | |
H4A | 0.1098 | 0.8179 | 1.0237 | 0.052* | |
C7 | 0.6964 (3) | 0.5855 (2) | 1.17056 (14) | 0.0377 (4) | |
C8 | 0.5837 (3) | 0.5375 (3) | 1.28599 (14) | 0.0403 (4) | |
H8A | 0.5045 | 0.4433 | 1.2833 | 0.048* | |
H8B | 0.4885 | 0.6546 | 1.3096 | 0.048* | |
C3 | 0.3558 (3) | 0.8462 (2) | 0.90829 (15) | 0.0396 (4) | |
C2 | 0.5691 (3) | 0.8107 (2) | 0.88940 (14) | 0.0394 (4) | |
C9 | 0.7250 (3) | 0.4561 (3) | 1.37097 (15) | 0.0438 (4) | |
H9A | 0.6499 | 0.3970 | 1.4368 | 0.053* | |
H9B | 0.8371 | 0.3554 | 1.3411 | 0.053* | |
N2 | 0.6857 (3) | 0.7499 (3) | 1.45984 (14) | 0.0580 (5) | |
C12 | 0.9975 (3) | 0.6333 (4) | 1.37805 (17) | 0.0594 (6) | |
H12A | 1.1073 | 0.5521 | 1.3389 | 0.071* | |
N3 | 1.0108 (4) | 0.7888 (3) | 1.41752 (17) | 0.0744 (6) | |
C13 | 0.8161 (5) | 0.8543 (4) | 1.46695 (18) | 0.0689 (7) | |
H13A | 0.7768 | 0.9653 | 1.5034 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0636 (3) | 0.0552 (3) | 0.0515 (3) | −0.0020 (2) | −0.0247 (2) | −0.0020 (2) |
Cl2 | 0.0628 (3) | 0.0730 (4) | 0.0343 (3) | −0.0149 (3) | −0.0007 (2) | −0.0001 (2) |
C6 | 0.0395 (9) | 0.0339 (8) | 0.0350 (8) | −0.0110 (7) | −0.0055 (7) | −0.0059 (6) |
O1 | 0.0388 (7) | 0.0748 (9) | 0.0416 (7) | −0.0087 (6) | −0.0049 (5) | −0.0029 (6) |
N1 | 0.0470 (8) | 0.0567 (9) | 0.0315 (7) | −0.0195 (7) | −0.0074 (6) | 0.0019 (6) |
C5 | 0.0390 (9) | 0.0425 (9) | 0.0395 (9) | −0.0127 (7) | −0.0030 (7) | −0.0014 (7) |
C1 | 0.0382 (9) | 0.0403 (8) | 0.0374 (9) | −0.0108 (7) | −0.0046 (7) | −0.0076 (7) |
C4 | 0.0384 (9) | 0.0426 (9) | 0.0501 (10) | −0.0096 (7) | −0.0084 (8) | −0.0033 (7) |
C7 | 0.0395 (9) | 0.0397 (8) | 0.0352 (9) | −0.0104 (7) | −0.0056 (7) | −0.0069 (7) |
C8 | 0.0402 (9) | 0.0454 (9) | 0.0368 (9) | −0.0138 (7) | −0.0048 (7) | −0.0040 (7) |
C3 | 0.0465 (9) | 0.0323 (8) | 0.0418 (9) | −0.0062 (7) | −0.0140 (7) | −0.0057 (6) |
C2 | 0.0488 (10) | 0.0364 (8) | 0.0339 (8) | −0.0128 (7) | −0.0036 (7) | −0.0062 (6) |
C9 | 0.0467 (10) | 0.0476 (10) | 0.0368 (9) | −0.0132 (8) | −0.0067 (7) | −0.0001 (7) |
N2 | 0.0692 (11) | 0.0622 (10) | 0.0461 (9) | −0.0237 (9) | −0.0020 (8) | −0.0116 (8) |
C12 | 0.0520 (11) | 0.0837 (15) | 0.0460 (11) | −0.0293 (11) | −0.0127 (9) | 0.0109 (10) |
N3 | 0.0877 (15) | 0.0959 (15) | 0.0591 (12) | −0.0577 (13) | −0.0323 (11) | 0.0180 (11) |
C13 | 0.109 (2) | 0.0717 (14) | 0.0412 (11) | −0.0455 (14) | −0.0217 (12) | 0.0023 (10) |
Cl1—C3 | 1.7291 (17) | C4—H4A | 0.9300 |
Cl2—C2 | 1.7262 (17) | C7—C8 | 1.517 (2) |
C6—C5 | 1.392 (2) | C8—C9 | 1.517 (3) |
C6—C1 | 1.391 (2) | C8—H8A | 0.9700 |
C6—C7 | 1.501 (2) | C8—H8B | 0.9700 |
O1—C7 | 1.214 (2) | C3—C2 | 1.394 (3) |
N1—C12 | 1.328 (3) | C9—H9A | 0.9700 |
N1—N2 | 1.359 (2) | C9—H9B | 0.9700 |
N1—C9 | 1.456 (2) | N2—C13 | 1.319 (3) |
C5—C4 | 1.385 (3) | C12—N3 | 1.312 (3) |
C5—H5A | 0.9300 | C12—H12A | 0.9300 |
C1—C2 | 1.387 (2) | N3—C13 | 1.352 (4) |
C1—H1A | 0.9300 | C13—H13A | 0.9300 |
C4—C3 | 1.377 (3) | ||
C5—C6—C1 | 119.26 (16) | C9—C8—H8B | 108.9 |
C5—C6—C7 | 122.57 (15) | H8A—C8—H8B | 107.7 |
C1—C6—C7 | 118.17 (15) | C4—C3—C2 | 120.29 (16) |
C12—N1—N2 | 109.21 (18) | C4—C3—Cl1 | 119.09 (14) |
C12—N1—C9 | 129.46 (19) | C2—C3—Cl1 | 120.62 (14) |
N2—N1—C9 | 121.32 (15) | C1—C2—C3 | 119.74 (16) |
C6—C5—C4 | 120.62 (16) | C1—C2—Cl2 | 119.54 (14) |
C6—C5—H5A | 119.7 | C3—C2—Cl2 | 120.72 (14) |
C4—C5—H5A | 119.7 | N1—C9—C8 | 111.80 (15) |
C2—C1—C6 | 120.24 (16) | N1—C9—H9A | 109.3 |
C2—C1—H1A | 119.9 | C8—C9—H9A | 109.3 |
C6—C1—H1A | 119.9 | N1—C9—H9B | 109.3 |
C3—C4—C5 | 119.83 (17) | C8—C9—H9B | 109.3 |
C3—C4—H4A | 120.1 | H9A—C9—H9B | 107.9 |
C5—C4—H4A | 120.1 | C13—N2—N1 | 102.01 (19) |
O1—C7—C6 | 120.27 (15) | N1—C12—N3 | 111.4 (2) |
O1—C7—C8 | 121.24 (15) | N1—C12—H12A | 124.3 |
C6—C7—C8 | 118.48 (14) | N3—C12—H12A | 124.3 |
C7—C8—C9 | 113.41 (15) | C12—N3—C13 | 102.06 (19) |
C7—C8—H8A | 108.9 | N2—C13—N3 | 115.3 (2) |
C9—C8—H8A | 108.9 | N2—C13—H13A | 122.4 |
C7—C8—H8B | 108.9 | N3—C13—H13A | 122.4 |
C1—C6—C5—C4 | 0.0 (2) | C4—C3—C2—C1 | −0.1 (2) |
C7—C6—C5—C4 | −179.28 (15) | Cl1—C3—C2—C1 | −179.96 (12) |
C5—C6—C1—C2 | 1.0 (2) | C4—C3—C2—Cl2 | 179.98 (13) |
C7—C6—C1—C2 | −179.72 (14) | Cl1—C3—C2—Cl2 | 0.1 (2) |
C6—C5—C4—C3 | −1.0 (3) | C12—N1—C9—C8 | −110.1 (2) |
C5—C6—C7—O1 | 177.26 (16) | N2—N1—C9—C8 | 68.8 (2) |
C1—C6—C7—O1 | −2.0 (2) | C7—C8—C9—N1 | 73.91 (19) |
C5—C6—C7—C8 | −2.3 (2) | C12—N1—N2—C13 | 0.3 (2) |
C1—C6—C7—C8 | 178.48 (14) | C9—N1—N2—C13 | −178.74 (16) |
O1—C7—C8—C9 | 3.7 (2) | N2—N1—C12—N3 | −0.5 (2) |
C6—C7—C8—C9 | −176.79 (14) | C9—N1—C12—N3 | 178.46 (17) |
C5—C4—C3—C2 | 1.1 (3) | N1—C12—N3—C13 | 0.4 (2) |
C5—C4—C3—Cl1 | −179.07 (13) | N1—N2—C13—N3 | −0.1 (2) |
C6—C1—C2—C3 | −0.9 (2) | C12—N3—C13—N2 | −0.2 (3) |
C6—C1—C2—Cl2 | 178.97 (12) |
Experimental details
Crystal data | |
Chemical formula | C11H9Cl2N3O |
Mr | 270.11 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 570.19 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.27 × 0.27 × 0.07 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.865, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3183, 2194, 1955 |
Rint | 0.009 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.108, 0.66 |
No. of reflections | 2194 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
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.