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In the title compound, C12H11Cl2N3O2, also referred to as aza­conazole, the five-membered 1,3-dioxolane ring assumes an envelope conformation. In the crystal packing, the mol­ecules are linked into an extended three-dimensional network by weak C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021386/rz2037sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021386/rz2037Isup2.hkl
Contains datablock I

CCDC reference: 614879

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.057
  • wR factor = 0.102
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.

1-{1-[2-(2,4-Dichlorophenyl)-1,3-dioxolan-2-yl]ethan-2-yl}-1H-1,2,4-triazole top
Crystal data top
C12H11Cl2N3O2Dx = 1.514 Mg m3
Mr = 300.14Melting point: 384.5-386.5 K K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 11.121 (2) Åθ = 4.6–9.0°
b = 7.2420 (14) ŵ = 0.49 mm1
c = 32.691 (7) ÅT = 298 K
V = 2632.9 (9) Å3Block, colourless
Z = 80.40 × 0.20 × 0.10 mm
F(000) = 1232
Data collection top
Enraf–Nonius CAD-4
diffractometer
1580 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 26.0°, θmin = 1.3°
ω/2θ scansh = 013
Absorption correction: ψ scan
(North et al., 1968)
k = 08
Tmin = 0.827, Tmax = 0.952l = 4040
5108 measured reflections3 standard reflections every 97 reflections
2584 independent reflections intensity decay: 8.4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.03P)2 + 0.55P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2584 reflectionsΔρmax = 0.24 e Å3
173 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0032 (4)
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
C10.1052 (4)0.8950 (5)0.77714 (10)0.0520 (9)
H10.07580.87150.80320.062*
C20.2334 (3)0.9306 (4)0.72863 (9)0.0400 (7)
H20.30570.93370.71440.048*
C30.1113 (3)1.0680 (4)0.67632 (8)0.0341 (6)
H3A0.18951.11190.66750.041*
H3B0.05791.17380.67740.041*
C40.0646 (2)0.9360 (4)0.64494 (8)0.0299 (6)
C50.0557 (3)0.6863 (4)0.64103 (10)0.0432 (7)
H5A0.08640.68240.61330.052*
H5B0.10670.61120.65840.052*
C60.0696 (3)0.6221 (4)0.64257 (10)0.0462 (8)
H6A0.08200.54290.66610.055*
H6B0.08930.55290.61810.055*
C70.0684 (3)1.0219 (4)0.60212 (8)0.0288 (6)
C80.1612 (3)0.9788 (4)0.57614 (8)0.0418 (7)
H80.21970.89650.58510.050*
C90.1717 (4)1.0523 (5)0.53726 (10)0.0570 (10)
H90.23531.01840.52040.068*
C100.0877 (4)1.1745 (4)0.52422 (10)0.0546 (10)
C110.0072 (3)1.2269 (5)0.54860 (10)0.0512 (9)
H110.06411.31120.53930.061*
C120.0157 (3)1.1498 (4)0.58775 (9)0.0371 (7)
Cl10.09895 (13)1.26951 (16)0.47526 (3)0.0924 (5)
Cl20.13660 (8)1.22504 (13)0.61728 (3)0.0609 (3)
N10.0439 (2)0.9657 (3)0.74647 (8)0.0436 (6)
N20.1230 (2)0.9945 (3)0.71681 (6)0.0297 (5)
N30.2117 (3)0.8647 (4)0.76479 (8)0.0506 (7)
O10.05002 (17)0.8721 (3)0.65571 (6)0.0346 (5)
O20.14193 (18)0.7812 (3)0.64547 (6)0.0365 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.069 (3)0.053 (2)0.0346 (17)0.0028 (19)0.0025 (16)0.0045 (15)
C20.0288 (17)0.0476 (19)0.0434 (18)0.0032 (13)0.0049 (13)0.0082 (14)
C30.0405 (16)0.0250 (13)0.0369 (15)0.0063 (12)0.0012 (13)0.0008 (12)
C40.0267 (14)0.0300 (14)0.0330 (15)0.0010 (11)0.0005 (11)0.0011 (11)
C50.0503 (19)0.0330 (17)0.0464 (18)0.0094 (15)0.0008 (15)0.0001 (13)
C60.052 (2)0.0292 (16)0.058 (2)0.0044 (15)0.0076 (16)0.0116 (15)
C70.0348 (15)0.0206 (12)0.0310 (14)0.0026 (11)0.0009 (11)0.0034 (11)
C80.0536 (19)0.0368 (16)0.0351 (16)0.0001 (15)0.0069 (14)0.0023 (12)
C90.078 (3)0.046 (2)0.0477 (19)0.0112 (19)0.0168 (19)0.0020 (17)
C100.086 (3)0.0395 (18)0.0388 (18)0.0262 (19)0.0092 (19)0.0065 (14)
C110.074 (2)0.0306 (16)0.0491 (19)0.0084 (17)0.0236 (19)0.0053 (15)
C120.0459 (17)0.0238 (14)0.0416 (16)0.0004 (13)0.0148 (13)0.0046 (13)
Cl10.1670 (13)0.0715 (7)0.0387 (5)0.0415 (8)0.0124 (6)0.0181 (5)
Cl20.0542 (5)0.0565 (5)0.0720 (6)0.0227 (4)0.0013 (5)0.0010 (5)
N10.0442 (15)0.0430 (14)0.0438 (14)0.0021 (12)0.0105 (12)0.0026 (12)
N20.0304 (13)0.0260 (11)0.0327 (12)0.0005 (9)0.0007 (10)0.0027 (10)
N30.0622 (19)0.0446 (16)0.0450 (16)0.0079 (14)0.0065 (14)0.0049 (13)
O10.0297 (10)0.0284 (10)0.0456 (11)0.0030 (8)0.0034 (10)0.0006 (9)
O20.0312 (10)0.0282 (10)0.0500 (12)0.0052 (9)0.0004 (9)0.0030 (9)
Geometric parameters (Å, º) top
C1—N31.271 (4)C5—H5B0.9700
C1—N11.316 (4)C6—O21.408 (4)
C1—H10.9300C6—H6A0.9700
C2—N31.297 (4)C6—H6B0.9700
C2—N21.368 (4)C7—C81.373 (4)
C2—H20.9300C7—C121.398 (4)
C3—N21.433 (3)C8—C91.383 (4)
C3—C41.495 (4)C8—H80.9300
C3—H3A0.9700C9—C101.356 (5)
C3—H3B0.9700C9—H90.9300
C4—O11.401 (3)C10—C111.376 (5)
C4—O21.413 (3)C10—Cl11.747 (3)
C4—C71.532 (4)C11—C121.400 (4)
C5—O11.430 (3)C11—H110.9300
C5—C61.470 (5)C12—Cl21.743 (3)
C5—H5A0.9700N1—N21.325 (3)
N3—C1—N1107.9 (3)C5—C6—H6B110.4
N3—C1—H1126.0H6A—C6—H6B108.6
N1—C1—H1126.0C8—C7—C12116.5 (3)
N3—C2—N2102.4 (3)C8—C7—C4119.6 (2)
N3—C2—H2128.8C12—C7—C4123.9 (3)
N2—C2—H2128.8C7—C8—C9123.0 (3)
N2—C3—C4115.3 (2)C7—C8—H8118.5
N2—C3—H3A108.4C9—C8—H8118.5
C4—C3—H3A108.4C10—C9—C8118.8 (3)
N2—C3—H3B108.4C10—C9—H9120.6
C4—C3—H3B108.4C8—C9—H9120.6
H3A—C3—H3B107.5C9—C10—C11121.8 (3)
O1—C4—O2106.7 (2)C9—C10—Cl1119.7 (3)
O1—C4—C3110.8 (2)C11—C10—Cl1118.5 (3)
O2—C4—C3106.7 (2)C10—C11—C12118.1 (3)
O1—C4—C7112.9 (2)C10—C11—H11120.9
O2—C4—C7108.5 (2)C12—C11—H11120.9
C3—C4—C7111.0 (2)C7—C12—C11121.8 (3)
O1—C5—C6104.2 (2)C7—C12—Cl2122.5 (2)
O1—C5—H5A110.9C11—C12—Cl2115.7 (2)
C6—C5—H5A110.9C1—N1—N2106.0 (3)
O1—C5—H5B110.9N1—N2—C2109.6 (2)
C6—C5—H5B110.9N1—N2—C3132.4 (2)
H5A—C5—H5B108.9C2—N2—C3117.9 (2)
O2—C6—C5106.5 (3)C1—N3—C2113.5 (3)
O2—C6—H6A110.4C4—O1—C5105.5 (2)
C5—C6—H6A110.4C6—O2—C4107.5 (2)
O2—C6—H6B110.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O20.932.312.689 (3)104
C3—H3A···O2i0.972.353.306 (4)168
Symmetry code: (i) x+1/2, y+1/2, z.
 

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