Bis(2,4,6-tri­chloro­phenyl) 2-ethyl­malonate

2-Ethyl-1,3-propane­dioic (malonic) acid forms a diester, bis(2,4,6-tri­chloro­phenyl) ester, with 2,4,6-tri­chloro­phenol to give the non-planar title compound, C₁₇H₁₀Cl₆O₄.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.103
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.94
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing ..          ?

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               3352
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3589
           Completeness (_total/calc)             93.40%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2A   ..  Cl2A     =       3.44 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C17 H10 Cl6 O4

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               3352
           From the CIF: _diffrn_reflns_limit_ max hkl    7.    9.   20.
           From the CIF: _diffrn_reflns_limit_ min hkl   -1.  -10.  -20.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl    9.   10.   20.
           Calculated minimum hkl   -9.  -10.  -20.

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SDP (Frenz & Enraf-Nonius, 1985); cell refinement: SDP; data reduction: WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.

syn-Bis(2,4,6-trichlorophenyl) 2-ethylmalonate

Crystal data

C17H10Cl6O4	Z = 2
Mr = 490.95	F(000) = 492
Triclinic, P1	Dx = 1.597 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.648 (3) Å	Cell parameters from 25 reflections
b = 8.532 (2) Å	θ = 10.0–12.0°
c = 16.947 (6) Å	µ = 0.86 mm^−1
α = 91.41 (2)°	T = 293 K
β = 92.98 (2)°	Plate, colourless
γ = 112.26 (2)°	0.20 × 0.15 × 0.15 mm
V = 1020.8 (6) Å^3

Data collection

Enraf-Nonius CAD-4 diffractometer	2430 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	Rint = 0.008
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
non–profiled ω/2θ scans	h = −1→7
Absorption correction: ψ scan (North et al., 1968)	k = −10→9
Tmin = 0.839, Tmax = 0.879	l = −20→20
3834 measured reflections	3 standard reflections every 60 min
3352 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0572P)^2 + 0.6749P] where P = (Fo^2 + 2Fc^2)/3
3352 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

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
C1	−0.3001 (4)	−0.1455 (3)	0.68878 (13)	0.0433 (6)
O1	−0.1924 (3)	−0.1357 (2)	0.62568 (10)	0.0498 (5)
O11	−0.3881 (3)	−0.0589 (3)	0.69682 (11)	0.0620 (5)
C2	−0.2853 (4)	−0.2813 (3)	0.74065 (13)	0.0475 (6)
H2	−0.1514	−0.2650	0.7479	0.057*
C21	−0.3933 (6)	−0.4569 (4)	0.70219 (17)	0.0713 (9)
H211	−0.5279	−0.4806	0.7009	0.086*
H212	−0.3587	−0.4585	0.6480	0.086*
C22	−0.3544 (7)	−0.5947 (4)	0.7452 (2)	0.0960 (13)
H221	−0.4241	−0.7024	0.7182	0.144*
H222	−0.3930	−0.5968	0.7983	0.144*
H223	−0.2215	−0.5724	0.7465	0.144*
C3	−0.3538 (4)	−0.2595 (3)	0.82098 (14)	0.0467 (6)
O3	−0.2059 (2)	−0.1560 (2)	0.86799 (9)	0.0492 (4)
O31	−0.5111 (3)	−0.3227 (3)	0.84130 (12)	0.0703 (6)
C1A	−0.1914 (4)	−0.0218 (3)	0.56882 (14)	0.0431 (6)
C2A	−0.2997 (4)	−0.0785 (3)	0.49804 (14)	0.0444 (6)
Cl2A	−0.45119 (12)	−0.28895 (9)	0.48649 (4)	0.0655 (2)
C3A	−0.2877 (4)	0.0281 (3)	0.43697 (14)	0.0476 (6)
H3A	−0.3621	−0.0109	0.3900	0.057*
C4A	−0.1628 (4)	0.1936 (3)	0.44752 (14)	0.0479 (6)
Cl4A	−0.14205 (13)	0.32926 (9)	0.37086 (4)	0.0683 (2)
C5A	−0.0519 (4)	0.2559 (3)	0.51702 (15)	0.0499 (7)
H5A	0.0319	0.3684	0.5228	0.060*
C6A	−0.0686 (4)	0.1466 (3)	0.57794 (14)	0.0462 (6)
Cl6A	0.06730 (12)	0.21929 (10)	0.66528 (4)	0.0666 (2)
C1B	−0.2368 (4)	−0.1216 (3)	0.94561 (14)	0.0448 (6)
C2B	−0.2435 (4)	0.0334 (3)	0.96610 (15)	0.0475 (6)
Cl2B	−0.23501 (12)	0.17321 (10)	0.89333 (4)	0.0678 (2)
C3B	−0.2534 (4)	0.0783 (4)	1.04424 (15)	0.0527 (7)
H3B	−0.2576	0.1829	1.0581	0.063*
C4B	−0.2569 (4)	−0.0354 (4)	1.10089 (15)	0.0532 (7)
Cl4B	−0.26373 (13)	0.02300 (13)	1.19905 (4)	0.0779 (3)
C5B	−0.2527 (4)	−0.1914 (4)	1.08224 (15)	0.0538 (7)
H5B	−0.2570	−0.2668	1.1215	0.065*
C6B	−0.2420 (4)	−0.2338 (3)	1.00388 (15)	0.0504 (7)
Cl6B	−0.22947 (13)	−0.42623 (10)	0.97877 (5)	0.0726 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0540 (16)	0.0462 (14)	0.0298 (12)	0.0196 (13)	0.0007 (11)	−0.0009 (10)
O1	0.0737 (13)	0.0492 (10)	0.0395 (9)	0.0360 (9)	0.0140 (9)	0.0137 (8)
O11	0.0808 (15)	0.0785 (14)	0.0455 (11)	0.0494 (13)	0.0153 (10)	0.0138 (9)
C2	0.0642 (18)	0.0459 (14)	0.0333 (12)	0.0221 (13)	0.0015 (12)	0.0039 (10)
C21	0.107 (3)	0.0478 (16)	0.0486 (16)	0.0187 (17)	−0.0002 (17)	0.0023 (13)
C22	0.160 (4)	0.0482 (18)	0.079 (2)	0.037 (2)	0.012 (2)	0.0161 (17)
C3	0.0523 (18)	0.0493 (15)	0.0376 (13)	0.0180 (13)	0.0022 (12)	0.0091 (11)
O3	0.0502 (11)	0.0570 (11)	0.0348 (9)	0.0137 (9)	0.0073 (8)	−0.0015 (8)
O31	0.0546 (14)	0.0921 (16)	0.0504 (11)	0.0127 (12)	0.0010 (10)	0.0033 (11)
C1A	0.0587 (17)	0.0428 (13)	0.0371 (12)	0.0285 (12)	0.0113 (11)	0.0084 (10)
C2A	0.0562 (16)	0.0381 (13)	0.0420 (13)	0.0211 (12)	0.0062 (12)	0.0010 (10)
Cl2A	0.0787 (5)	0.0437 (4)	0.0644 (4)	0.0129 (3)	0.0012 (4)	0.0008 (3)
C3A	0.0637 (18)	0.0501 (15)	0.0353 (13)	0.0294 (13)	−0.0009 (12)	−0.0007 (11)
C4A	0.0713 (19)	0.0438 (14)	0.0383 (13)	0.0323 (14)	0.0062 (12)	0.0072 (11)
Cl4A	0.1080 (7)	0.0558 (4)	0.0471 (4)	0.0373 (4)	0.0035 (4)	0.0171 (3)
C5A	0.0664 (18)	0.0373 (13)	0.0486 (15)	0.0223 (13)	0.0035 (13)	0.0049 (11)
C6A	0.0616 (17)	0.0462 (14)	0.0368 (13)	0.0276 (13)	0.0016 (12)	0.0004 (11)
Cl6A	0.0870 (6)	0.0615 (4)	0.0466 (4)	0.0256 (4)	−0.0152 (4)	−0.0017 (3)
C1B	0.0423 (15)	0.0569 (15)	0.0329 (12)	0.0162 (12)	0.0038 (10)	0.0000 (11)
C2B	0.0466 (16)	0.0559 (16)	0.0415 (14)	0.0213 (13)	0.0002 (11)	0.0057 (12)
Cl2B	0.0865 (6)	0.0651 (5)	0.0568 (4)	0.0348 (4)	−0.0030 (4)	0.0137 (3)
C3B	0.0494 (17)	0.0626 (17)	0.0486 (15)	0.0249 (14)	0.0012 (12)	−0.0079 (13)
C4B	0.0466 (16)	0.0769 (19)	0.0343 (13)	0.0213 (14)	0.0043 (11)	−0.0018 (13)
Cl4B	0.0824 (6)	0.1130 (7)	0.0388 (4)	0.0378 (5)	0.0084 (4)	−0.0102 (4)
C5B	0.0576 (18)	0.0674 (18)	0.0390 (14)	0.0258 (15)	0.0055 (12)	0.0103 (12)
C6B	0.0544 (17)	0.0537 (15)	0.0450 (14)	0.0219 (13)	0.0070 (12)	0.0050 (12)
Cl6B	0.1014 (7)	0.0584 (4)	0.0660 (5)	0.0391 (4)	0.0079 (4)	0.0063 (4)

Geometric parameters (Å, º)

C1—O11	1.183 (3)	C2A—Cl2A	1.728 (3)
C1—O1	1.369 (3)	C3A—C4A	1.374 (4)
C1—C2	1.506 (4)	C3A—H3A	0.9300
O1—C1A	1.384 (3)	C4A—C5A	1.383 (4)
C2—C3	1.516 (4)	C4A—Cl4A	1.735 (2)
C2—C21	1.520 (4)	C5A—C6A	1.386 (3)
C2—H2	0.9800	C5A—H5A	0.9300
C21—C22	1.512 (5)	C6A—Cl6A	1.721 (3)
C21—H211	0.9700	C1B—C2B	1.380 (4)
C21—H212	0.9700	C1B—C6B	1.384 (4)
C22—H221	0.9600	C2B—C3B	1.383 (4)
C22—H222	0.9600	C2B—Cl2B	1.723 (3)
C22—H223	0.9600	C3B—C4B	1.375 (4)
C3—O31	1.190 (3)	C3B—H3B	0.9300
C3—O3	1.345 (3)	C4B—C5B	1.373 (4)
O3—C1B	1.392 (3)	C4B—Cl4B	1.734 (3)
C1A—C6A	1.386 (4)	C5B—C6B	1.382 (4)
C1A—C2A	1.387 (4)	C5B—H5B	0.9300
C2A—C3A	1.378 (3)	C6B—Cl6B	1.725 (3)
O11—C1—O1	122.6 (2)	C1A—C2A—Cl2A	118.71 (19)
O11—C1—C2	129.1 (2)	C4A—C3A—C2A	118.1 (2)
O1—C1—C2	108.4 (2)	C4A—C3A—H3A	121.0
C1—O1—C1A	117.8 (2)	C2A—C3A—H3A	121.0
C1—C2—C3	108.8 (2)	C3A—C4A—C5A	122.3 (2)
C1—C2—C21	111.2 (2)	C3A—C4A—Cl4A	118.9 (2)
C3—C2—C21	112.4 (2)	C5A—C4A—Cl4A	118.7 (2)
C1—C2—H2	108.1	C4A—C5A—C6A	118.4 (2)
C3—C2—H2	108.1	C4A—C5A—H5A	120.8
C21—C2—H2	108.1	C6A—C5A—H5A	120.8
C22—C21—C2	112.8 (3)	C1A—C6A—C5A	120.7 (2)
C22—C21—H211	109.0	C1A—C6A—Cl6A	119.48 (19)
C2—C21—H211	109.0	C5A—C6A—Cl6A	119.8 (2)
C22—C21—H212	109.0	C2B—C1B—C6B	119.5 (2)
C2—C21—H212	109.0	C2B—C1B—O3	119.4 (2)
H211—C21—H212	107.8	C6B—C1B—O3	120.8 (2)
C21—C22—H221	109.5	C1B—C2B—C3B	120.7 (2)
C21—C22—H222	109.5	C1B—C2B—Cl2B	119.26 (19)
H221—C22—H222	109.5	C3B—C2B—Cl2B	120.0 (2)
C21—C22—H223	109.5	C4B—C3B—C2B	118.5 (3)
H221—C22—H223	109.5	C4B—C3B—H3B	120.8
H222—C22—H223	109.5	C2B—C3B—H3B	120.8
O31—C3—O3	124.1 (2)	C5B—C4B—C3B	122.2 (2)
O31—C3—C2	127.1 (3)	C5B—C4B—Cl4B	119.4 (2)
O3—C3—C2	108.9 (2)	C3B—C4B—Cl4B	118.4 (2)
C3—O3—C1B	118.4 (2)	C4B—C5B—C6B	118.5 (3)
O1—C1A—C6A	120.8 (2)	C4B—C5B—H5B	120.7
O1—C1A—C2A	120.1 (2)	C6B—C5B—H5B	120.7
C6A—C1A—C2A	118.8 (2)	C5B—C6B—C1B	120.6 (3)
C3A—C2A—C1A	121.6 (2)	C5B—C6B—Cl6B	119.7 (2)
C3A—C2A—Cl2A	119.6 (2)	C1B—C6B—Cl6B	119.7 (2)
C2A—C1A—O1—C1	−101.4 (3)	C1—C2—C3—O3	−90.0 (3)
C1A—O1—C1—C2	177.8 (2)	C2—C3—O3—C1B	−178.6 (2)
O1—C1—C2—C3	163.6 (2)	C3—O3—C1B—C2B	−104.3 (3)