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In the title compound, C16H19Cl2N3O2, the dihedral angle between the two rings is 86.26 (2)°. The crystal packing is stabilized mainly by van der Waals inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044989/wk2032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044989/wk2032Isup2.hkl
Contains datablock I

CCDC reference: 630494

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.075
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O3 .. 3.15 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.36 From the CIF: _reflns_number_total 3673 Count of symmetry unique reflns 2110 Completeness (_total/calc) 174.08% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1563 Fraction of Friedel pairs measured 0.741 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butyl chloroacetate top
Crystal data top
C16H19Cl2N3O3F(000) = 776
Mr = 372.24Dx = 1.374 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3079 reflections
a = 10.1456 (15) Åθ = 2.3–23.0°
b = 10.7610 (17) ŵ = 0.38 mm1
c = 16.481 (3) ÅT = 294 K
V = 1799.3 (5) Å3Block, colourless
Z = 40.24 × 0.20 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3673 independent reflections
Radiation source: fine-focus sealed tube2765 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1112
Tmin = 0.914, Tmax = 0.963k = 1313
10202 measured reflectionsl = 209
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0286P)2 + 0.1498P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3673 reflectionsΔρmax = 0.17 e Å3
221 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.28 (6)
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
Cl10.34319 (6)0.77486 (6)0.84194 (4)0.05254 (19)
Cl20.93370 (7)1.33197 (6)0.51291 (4)0.0573 (2)
O10.77112 (14)0.95650 (14)0.63312 (9)0.0355 (4)
O20.97938 (14)1.07624 (14)0.55306 (9)0.0377 (4)
O31.19004 (17)1.0934 (2)0.59502 (13)0.0710 (6)
N10.96115 (17)0.97803 (17)0.71195 (11)0.0332 (4)
C80.9432 (2)1.0930 (2)0.73998 (14)0.0444 (6)
H80.88001.14810.72060.053*
C91.0964 (3)1.0119 (2)0.80335 (16)0.0512 (7)
H91.16481.00150.84030.061*
C10.6763 (2)0.9087 (2)0.68504 (13)0.0312 (5)
C20.7002 (2)0.8228 (2)0.74538 (13)0.0362 (6)
H20.78500.79270.75380.043*
C30.5968 (2)0.7817 (2)0.79332 (14)0.0389 (6)
H30.61200.72480.83470.047*
C40.4722 (2)0.8256 (2)0.77941 (14)0.0363 (6)
C50.4472 (2)0.9104 (2)0.71893 (14)0.0406 (6)
H50.36190.93930.71030.049*
C60.5492 (2)0.9521 (2)0.67143 (13)0.0376 (6)
H60.53331.00920.63020.045*
C70.9023 (2)0.9151 (2)0.64178 (13)0.0316 (5)
H70.90230.82520.65140.038*
N21.0617 (2)0.92339 (19)0.75238 (12)0.0477 (5)
N31.0272 (2)1.11821 (19)0.79882 (13)0.0509 (6)
C100.9788 (2)0.9426 (2)0.56531 (13)0.0346 (5)
H101.07020.91680.57470.041*
C110.9325 (2)0.8801 (2)0.48588 (14)0.0427 (6)
C120.9114 (3)0.7416 (3)0.50216 (17)0.0691 (8)
H12A0.89470.69940.45190.104*
H12B0.83730.73090.53770.104*
H12C0.98880.70740.52710.104*
C130.8066 (3)0.9381 (3)0.45178 (17)0.0692 (9)
H13A0.78700.90170.40000.104*
H13B0.81881.02600.44560.104*
H13C0.73480.92290.48840.104*
C141.0427 (3)0.8963 (3)0.42295 (16)0.0667 (8)
H14A1.06010.98320.41530.100*
H14B1.01570.86020.37230.100*
H14C1.12110.85570.44180.100*
C151.0899 (3)1.1391 (2)0.57084 (15)0.0440 (6)
C161.0789 (3)1.2760 (2)0.55924 (17)0.0581 (7)
H16A1.15341.30310.52680.070*
H16B1.08701.31530.61200.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0357 (3)0.0624 (4)0.0595 (4)0.0052 (3)0.0082 (3)0.0107 (4)
Cl20.0671 (5)0.0502 (4)0.0545 (4)0.0016 (3)0.0023 (4)0.0041 (3)
O10.0272 (8)0.0431 (10)0.0362 (9)0.0009 (7)0.0002 (7)0.0094 (7)
O20.0347 (9)0.0358 (9)0.0426 (9)0.0039 (7)0.0023 (7)0.0047 (8)
O30.0396 (11)0.0720 (14)0.1016 (16)0.0136 (11)0.0158 (11)0.0202 (13)
N10.0333 (10)0.0342 (11)0.0322 (10)0.0011 (9)0.0048 (9)0.0013 (9)
C80.0447 (14)0.0392 (15)0.0492 (15)0.0056 (13)0.0060 (14)0.0039 (12)
C90.0560 (16)0.0463 (17)0.0512 (16)0.0026 (14)0.0190 (14)0.0014 (13)
C10.0296 (12)0.0334 (13)0.0306 (12)0.0029 (10)0.0008 (10)0.0028 (10)
C20.0276 (12)0.0439 (14)0.0370 (13)0.0025 (10)0.0024 (10)0.0031 (12)
C30.0369 (13)0.0464 (14)0.0333 (13)0.0009 (12)0.0007 (11)0.0081 (12)
C40.0305 (12)0.0406 (14)0.0378 (13)0.0044 (11)0.0030 (11)0.0005 (12)
C50.0289 (12)0.0448 (15)0.0480 (15)0.0036 (12)0.0023 (12)0.0023 (12)
C60.0352 (13)0.0415 (14)0.0359 (13)0.0036 (11)0.0017 (11)0.0072 (11)
C70.0302 (12)0.0297 (12)0.0348 (13)0.0003 (10)0.0013 (11)0.0003 (10)
N20.0507 (12)0.0429 (12)0.0495 (12)0.0057 (11)0.0180 (12)0.0008 (10)
N30.0580 (13)0.0445 (14)0.0503 (13)0.0006 (11)0.0132 (12)0.0046 (11)
C100.0309 (12)0.0342 (14)0.0385 (13)0.0001 (10)0.0010 (11)0.0034 (11)
C110.0502 (14)0.0426 (14)0.0352 (13)0.0000 (12)0.0013 (13)0.0011 (11)
C120.109 (2)0.0501 (17)0.0485 (15)0.0088 (17)0.0094 (17)0.0094 (13)
C130.0662 (19)0.095 (2)0.0464 (17)0.0110 (18)0.0179 (15)0.0121 (17)
C140.074 (2)0.080 (2)0.0461 (16)0.0062 (17)0.0198 (17)0.0022 (15)
C150.0413 (15)0.0502 (17)0.0405 (15)0.0151 (13)0.0030 (13)0.0083 (12)
C160.0618 (17)0.0529 (17)0.0595 (16)0.0159 (15)0.0127 (15)0.0001 (14)
Geometric parameters (Å, º) top
Cl1—C41.753 (2)C5—C61.373 (3)
Cl2—C161.765 (3)C5—H50.9300
O1—C11.386 (2)C6—H60.9300
O1—C71.411 (2)C7—C101.509 (3)
O2—C151.342 (3)C7—H70.9800
O2—C101.452 (3)C10—C111.545 (3)
O3—C151.197 (3)C10—H100.9800
N1—C81.333 (3)C11—C131.529 (3)
N1—N21.353 (2)C11—C121.530 (4)
N1—C71.467 (3)C11—C141.535 (3)
C8—N31.319 (3)C12—H12A0.9600
C8—H80.9300C12—H12B0.9600
C9—N21.318 (3)C12—H12C0.9600
C9—N31.344 (3)C13—H13A0.9600
C9—H90.9300C13—H13B0.9600
C1—C21.379 (3)C13—H13C0.9600
C1—C61.390 (3)C14—H14A0.9600
C2—C31.386 (3)C14—H14B0.9600
C2—H20.9300C14—H14C0.9600
C3—C41.369 (3)C15—C161.491 (3)
C3—H30.9300C16—H16A0.9700
C4—C51.375 (3)C16—H16B0.9700
C1—O1—C7118.36 (16)O2—C10—C11108.35 (17)
C15—O2—C10118.16 (18)C7—C10—C11117.75 (18)
C8—N1—N2109.59 (19)O2—C10—H10107.4
C8—N1—C7130.26 (19)C7—C10—H10107.4
N2—N1—C7119.63 (18)C11—C10—H10107.4
N3—C8—N1111.0 (2)C13—C11—C12110.2 (2)
N3—C8—H8124.5C13—C11—C14108.3 (2)
N1—C8—H8124.5C12—C11—C14109.4 (2)
N2—C9—N3116.1 (2)C13—C11—C10112.8 (2)
N2—C9—H9121.9C12—C11—C10108.57 (19)
N3—C9—H9121.9C14—C11—C10107.6 (2)
C2—C1—O1124.89 (19)C11—C12—H12A109.5
C2—C1—C6120.3 (2)C11—C12—H12B109.5
O1—C1—C6114.83 (19)H12A—C12—H12B109.5
C1—C2—C3119.5 (2)C11—C12—H12C109.5
C1—C2—H2120.3H12A—C12—H12C109.5
C3—C2—H2120.3H12B—C12—H12C109.5
C4—C3—C2119.6 (2)C11—C13—H13A109.5
C4—C3—H3120.2C11—C13—H13B109.5
C2—C3—H3120.2H13A—C13—H13B109.5
C3—C4—C5121.4 (2)C11—C13—H13C109.5
C3—C4—Cl1118.95 (17)H13A—C13—H13C109.5
C5—C4—Cl1119.68 (17)H13B—C13—H13C109.5
C6—C5—C4119.4 (2)C11—C14—H14A109.5
C6—C5—H5120.3C11—C14—H14B109.5
C4—C5—H5120.3H14A—C14—H14B109.5
C5—C6—C1119.9 (2)C11—C14—H14C109.5
C5—C6—H6120.1H14A—C14—H14C109.5
C1—C6—H6120.1H14B—C14—H14C109.5
O1—C7—N1108.53 (17)O3—C15—O2125.1 (2)
O1—C7—C10109.79 (17)O3—C15—C16120.8 (2)
N1—C7—C10111.00 (17)O2—C15—C16114.1 (2)
O1—C7—H7109.2C15—C16—Cl2117.07 (19)
N1—C7—H7109.2C15—C16—H16A108.0
C10—C7—H7109.2Cl2—C16—H16A108.0
C9—N2—N1101.6 (2)C15—C16—H16B108.0
C8—N3—C9101.7 (2)Cl2—C16—H16B108.0
O2—C10—C7108.22 (17)H16A—C16—H16B107.3
N2—N1—C8—N30.7 (3)C8—N1—N2—C90.5 (3)
C7—N1—C8—N3172.24 (19)C7—N1—N2—C9173.10 (19)
C7—O1—C1—C20.0 (3)N1—C8—N3—C90.5 (3)
C7—O1—C1—C6178.63 (19)N2—C9—N3—C80.2 (3)
O1—C1—C2—C3179.8 (2)C15—O2—C10—C7103.7 (2)
C6—C1—C2—C31.2 (3)C15—O2—C10—C11127.6 (2)
C1—C2—C3—C40.9 (3)O1—C7—C10—O261.3 (2)
C2—C3—C4—C50.4 (4)N1—C7—C10—O258.7 (2)
C2—C3—C4—Cl1178.76 (18)O1—C7—C10—C1161.9 (2)
C3—C4—C5—C60.0 (4)N1—C7—C10—C11178.14 (18)
Cl1—C4—C5—C6178.41 (18)O2—C10—C11—C1349.0 (3)
C4—C5—C6—C10.3 (3)C7—C10—C11—C1374.1 (3)
C2—C1—C6—C50.9 (3)O2—C10—C11—C12171.4 (2)
O1—C1—C6—C5179.58 (19)C7—C10—C11—C1248.3 (3)
C1—O1—C7—N177.3 (2)O2—C10—C11—C1470.3 (2)
C1—O1—C7—C10161.26 (17)C7—C10—C11—C14166.5 (2)
C8—N1—C7—O135.1 (3)C10—O2—C15—O31.3 (4)
N2—N1—C7—O1154.09 (18)C10—O2—C15—C16177.8 (2)
C8—N1—C7—C1085.6 (3)O3—C15—C16—Cl2173.2 (2)
N2—N1—C7—C1085.2 (2)O2—C15—C16—Cl27.7 (3)
N3—C9—N2—N10.2 (3)
 

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