1-(4-Chloro­phen­oxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butyl chloro­acetate

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.

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

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Computing details

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

Crystal data

C16H19Cl2N3O3	F(000) = 776
Mr = 372.24	Dx = 1.374 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3079 reflections
a = 10.1456 (15) Å	θ = 2.3–23.0°
b = 10.7610 (17) Å	µ = 0.38 mm^−1
c = 16.481 (3) Å	T = 294 K
V = 1799.3 (5) Å^3	Block, colourless
Z = 4	0.24 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3673 independent reflections
Radiation source: fine-focus sealed tube	2765 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.914, Tmax = 0.963	k = −13→13
10202 measured reflections	l = −20→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.0286P)^2 + 0.1498P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3673 reflections	Δρmax = 0.17 e Å^−3
221 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.28 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.34319 (6)	0.77486 (6)	0.84194 (4)	0.05254 (19)
Cl2	0.93370 (7)	1.33197 (6)	0.51291 (4)	0.0573 (2)
O1	0.77112 (14)	0.95650 (14)	0.63312 (9)	0.0355 (4)
O2	0.97938 (14)	1.07624 (14)	0.55306 (9)	0.0377 (4)
O3	1.19004 (17)	1.0934 (2)	0.59502 (13)	0.0710 (6)
N1	0.96115 (17)	0.97803 (17)	0.71195 (11)	0.0332 (4)
C8	0.9432 (2)	1.0930 (2)	0.73998 (14)	0.0444 (6)
H8	0.8800	1.1481	0.7206	0.053*
C9	1.0964 (3)	1.0119 (2)	0.80335 (16)	0.0512 (7)
H9	1.1648	1.0015	0.8403	0.061*
C1	0.6763 (2)	0.9087 (2)	0.68504 (13)	0.0312 (5)
C2	0.7002 (2)	0.8228 (2)	0.74538 (13)	0.0362 (6)
H2	0.7850	0.7927	0.7538	0.043*
C3	0.5968 (2)	0.7817 (2)	0.79332 (14)	0.0389 (6)
H3	0.6120	0.7248	0.8347	0.047*
C4	0.4722 (2)	0.8256 (2)	0.77941 (14)	0.0363 (6)
C5	0.4472 (2)	0.9104 (2)	0.71893 (14)	0.0406 (6)
H5	0.3619	0.9393	0.7103	0.049*
C6	0.5492 (2)	0.9521 (2)	0.67143 (13)	0.0376 (6)
H6	0.5333	1.0092	0.6302	0.045*
C7	0.9023 (2)	0.9151 (2)	0.64178 (13)	0.0316 (5)
H7	0.9023	0.8252	0.6514	0.038*
N2	1.0617 (2)	0.92339 (19)	0.75238 (12)	0.0477 (5)
N3	1.0272 (2)	1.11821 (19)	0.79882 (13)	0.0509 (6)
C10	0.9788 (2)	0.9426 (2)	0.56531 (13)	0.0346 (5)
H10	1.0702	0.9168	0.5747	0.041*
C11	0.9325 (2)	0.8801 (2)	0.48588 (14)	0.0427 (6)
C12	0.9114 (3)	0.7416 (3)	0.50216 (17)	0.0691 (8)
H12A	0.8947	0.6994	0.4519	0.104*
H12B	0.8373	0.7309	0.5377	0.104*
H12C	0.9888	0.7074	0.5271	0.104*
C13	0.8066 (3)	0.9381 (3)	0.45178 (17)	0.0692 (9)
H13A	0.7870	0.9017	0.4000	0.104*
H13B	0.8188	1.0260	0.4456	0.104*
H13C	0.7348	0.9229	0.4884	0.104*
C14	1.0427 (3)	0.8963 (3)	0.42295 (16)	0.0667 (8)
H14A	1.0601	0.9832	0.4153	0.100*
H14B	1.0157	0.8602	0.3723	0.100*
H14C	1.1211	0.8557	0.4418	0.100*
C15	1.0899 (3)	1.1391 (2)	0.57084 (15)	0.0440 (6)
C16	1.0789 (3)	1.2760 (2)	0.55924 (17)	0.0581 (7)
H16A	1.1534	1.3031	0.5268	0.070*
H16B	1.0870	1.3153	0.6120	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0357 (3)	0.0624 (4)	0.0595 (4)	−0.0052 (3)	0.0082 (3)	0.0107 (4)
Cl2	0.0671 (5)	0.0502 (4)	0.0545 (4)	0.0016 (3)	0.0023 (4)	0.0041 (3)
O1	0.0272 (8)	0.0431 (10)	0.0362 (9)	0.0009 (7)	0.0002 (7)	0.0094 (7)
O2	0.0347 (9)	0.0358 (9)	0.0426 (9)	−0.0039 (7)	−0.0023 (7)	0.0047 (8)
O3	0.0396 (11)	0.0720 (14)	0.1016 (16)	−0.0136 (11)	−0.0158 (11)	0.0202 (13)
N1	0.0333 (10)	0.0342 (11)	0.0322 (10)	0.0011 (9)	−0.0048 (9)	0.0013 (9)
C8	0.0447 (14)	0.0392 (15)	0.0492 (15)	0.0056 (13)	−0.0060 (14)	−0.0039 (12)
C9	0.0560 (16)	0.0463 (17)	0.0512 (16)	−0.0026 (14)	−0.0190 (14)	0.0014 (13)
C1	0.0296 (12)	0.0334 (13)	0.0306 (12)	−0.0029 (10)	−0.0008 (10)	−0.0028 (10)
C2	0.0276 (12)	0.0439 (14)	0.0370 (13)	0.0025 (10)	−0.0024 (10)	0.0031 (12)
C3	0.0369 (13)	0.0464 (14)	0.0333 (13)	−0.0009 (12)	−0.0007 (11)	0.0081 (12)
C4	0.0305 (12)	0.0406 (14)	0.0378 (13)	−0.0044 (11)	0.0030 (11)	−0.0005 (12)
C5	0.0289 (12)	0.0448 (15)	0.0480 (15)	0.0036 (12)	−0.0023 (12)	−0.0023 (12)
C6	0.0352 (13)	0.0415 (14)	0.0359 (13)	0.0036 (11)	−0.0017 (11)	0.0072 (11)
C7	0.0302 (12)	0.0297 (12)	0.0348 (13)	0.0003 (10)	−0.0013 (11)	−0.0003 (10)
N2	0.0507 (12)	0.0429 (12)	0.0495 (12)	0.0057 (11)	−0.0180 (12)	0.0008 (10)
N3	0.0580 (13)	0.0445 (14)	0.0503 (13)	−0.0006 (11)	−0.0132 (12)	−0.0046 (11)
C10	0.0309 (12)	0.0342 (14)	0.0385 (13)	0.0001 (10)	0.0010 (11)	0.0034 (11)
C11	0.0502 (14)	0.0426 (14)	0.0352 (13)	0.0000 (12)	0.0013 (13)	−0.0011 (11)
C12	0.109 (2)	0.0501 (17)	0.0485 (15)	−0.0088 (17)	0.0094 (17)	−0.0094 (13)
C13	0.0662 (19)	0.095 (2)	0.0464 (17)	0.0110 (18)	−0.0179 (15)	−0.0121 (17)
C14	0.074 (2)	0.080 (2)	0.0461 (16)	0.0062 (17)	0.0198 (17)	0.0022 (15)
C15	0.0413 (15)	0.0502 (17)	0.0405 (15)	−0.0151 (13)	0.0030 (13)	0.0083 (12)
C16	0.0618 (17)	0.0529 (17)	0.0595 (16)	−0.0159 (15)	−0.0127 (15)	0.0001 (14)

Geometric parameters (Å, º)

Cl1—C4	1.753 (2)	C5—C6	1.373 (3)
Cl2—C16	1.765 (3)	C5—H5	0.9300
O1—C1	1.386 (2)	C6—H6	0.9300
O1—C7	1.411 (2)	C7—C10	1.509 (3)
O2—C15	1.342 (3)	C7—H7	0.9800
O2—C10	1.452 (3)	C10—C11	1.545 (3)
O3—C15	1.197 (3)	C10—H10	0.9800
N1—C8	1.333 (3)	C11—C13	1.529 (3)
N1—N2	1.353 (2)	C11—C12	1.530 (4)
N1—C7	1.467 (3)	C11—C14	1.535 (3)
C8—N3	1.319 (3)	C12—H12A	0.9600
C8—H8	0.9300	C12—H12B	0.9600
C9—N2	1.318 (3)	C12—H12C	0.9600
C9—N3	1.344 (3)	C13—H13A	0.9600
C9—H9	0.9300	C13—H13B	0.9600
C1—C2	1.379 (3)	C13—H13C	0.9600
C1—C6	1.390 (3)	C14—H14A	0.9600
C2—C3	1.386 (3)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.369 (3)	C15—C16	1.491 (3)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.375 (3)	C16—H16B	0.9700
C1—O1—C7	118.36 (16)	O2—C10—C11	108.35 (17)
C15—O2—C10	118.16 (18)	C7—C10—C11	117.75 (18)
C8—N1—N2	109.59 (19)	O2—C10—H10	107.4
C8—N1—C7	130.26 (19)	C7—C10—H10	107.4
N2—N1—C7	119.63 (18)	C11—C10—H10	107.4
N3—C8—N1	111.0 (2)	C13—C11—C12	110.2 (2)
N3—C8—H8	124.5	C13—C11—C14	108.3 (2)
N1—C8—H8	124.5	C12—C11—C14	109.4 (2)
N2—C9—N3	116.1 (2)	C13—C11—C10	112.8 (2)
N2—C9—H9	121.9	C12—C11—C10	108.57 (19)
N3—C9—H9	121.9	C14—C11—C10	107.6 (2)
C2—C1—O1	124.89 (19)	C11—C12—H12A	109.5
C2—C1—C6	120.3 (2)	C11—C12—H12B	109.5
O1—C1—C6	114.83 (19)	H12A—C12—H12B	109.5
C1—C2—C3	119.5 (2)	C11—C12—H12C	109.5
C1—C2—H2	120.3	H12A—C12—H12C	109.5
C3—C2—H2	120.3	H12B—C12—H12C	109.5
C4—C3—C2	119.6 (2)	C11—C13—H13A	109.5
C4—C3—H3	120.2	C11—C13—H13B	109.5
C2—C3—H3	120.2	H13A—C13—H13B	109.5
C3—C4—C5	121.4 (2)	C11—C13—H13C	109.5
C3—C4—Cl1	118.95 (17)	H13A—C13—H13C	109.5
C5—C4—Cl1	119.68 (17)	H13B—C13—H13C	109.5
C6—C5—C4	119.4 (2)	C11—C14—H14A	109.5
C6—C5—H5	120.3	C11—C14—H14B	109.5
C4—C5—H5	120.3	H14A—C14—H14B	109.5
C5—C6—C1	119.9 (2)	C11—C14—H14C	109.5
C5—C6—H6	120.1	H14A—C14—H14C	109.5
C1—C6—H6	120.1	H14B—C14—H14C	109.5
O1—C7—N1	108.53 (17)	O3—C15—O2	125.1 (2)
O1—C7—C10	109.79 (17)	O3—C15—C16	120.8 (2)
N1—C7—C10	111.00 (17)	O2—C15—C16	114.1 (2)
O1—C7—H7	109.2	C15—C16—Cl2	117.07 (19)
N1—C7—H7	109.2	C15—C16—H16A	108.0
C10—C7—H7	109.2	Cl2—C16—H16A	108.0
C9—N2—N1	101.6 (2)	C15—C16—H16B	108.0
C8—N3—C9	101.7 (2)	Cl2—C16—H16B	108.0
O2—C10—C7	108.22 (17)	H16A—C16—H16B	107.3
N2—N1—C8—N3	−0.7 (3)	C8—N1—N2—C9	0.5 (3)
C7—N1—C8—N3	−172.24 (19)	C7—N1—N2—C9	173.10 (19)
C7—O1—C1—C2	0.0 (3)	N1—C8—N3—C9	0.5 (3)
C7—O1—C1—C6	−178.63 (19)	N2—C9—N3—C8	−0.2 (3)
O1—C1—C2—C3	−179.8 (2)	C15—O2—C10—C7	103.7 (2)
C6—C1—C2—C3	−1.2 (3)	C15—O2—C10—C11	−127.6 (2)
C1—C2—C3—C4	0.9 (3)	O1—C7—C10—O2	61.3 (2)
C2—C3—C4—C5	−0.4 (4)	N1—C7—C10—O2	−58.7 (2)
C2—C3—C4—Cl1	−178.76 (18)	O1—C7—C10—C11	−61.9 (2)
C3—C4—C5—C6	0.0 (4)	N1—C7—C10—C11	178.14 (18)
Cl1—C4—C5—C6	178.41 (18)	O2—C10—C11—C13	−49.0 (3)
C4—C5—C6—C1	−0.3 (3)	C7—C10—C11—C13	74.1 (3)
C2—C1—C6—C5	0.9 (3)	O2—C10—C11—C12	−171.4 (2)
O1—C1—C6—C5	179.58 (19)	C7—C10—C11—C12	−48.3 (3)
C1—O1—C7—N1	−77.3 (2)	O2—C10—C11—C14	70.3 (2)
C1—O1—C7—C10	161.26 (17)	C7—C10—C11—C14	−166.5 (2)
C8—N1—C7—O1	−35.1 (3)	C10—O2—C15—O3	1.3 (4)
N2—N1—C7—O1	154.09 (18)	C10—O2—C15—C16	−177.8 (2)
C8—N1—C7—C10	85.6 (3)	O3—C15—C16—Cl2	173.2 (2)
N2—N1—C7—C10	−85.2 (2)	O2—C15—C16—Cl2	−7.7 (3)
N3—C9—N2—N1	−0.2 (3)