Download citation
Download citation
link to html
The crystal structure of 2-chloro-1-(2,4,5-trichloro­phen­yl)vinyl dimethyl phosphate (also known as Tetra­chlorvinphos, Stirofos, and Gardona®), C10H9Cl4O4P, contains two mol­ecules per asymmetric unit. In one of the mol­ecules, three O atoms of the phosphate group are disordered. Increased precision is presented compared to a previously reported structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033368/ci2124sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033368/ci2124Isup2.hkl
Contains datablock I

CCDC reference: 620746

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.043
  • wR factor = 0.116
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT772_ALERT_2_A Suspect O-H Bond in CIF: O3AA -H9AF .. 1.31 Ang.
Author Response: This is an artifact of the disorder of the oxygen atoms bonded to the methyl groups.
PLAT772_ALERT_2_A Suspect O-H Bond in CIF:      O4AA   -H10F    ..       1.34 Ang.
Author Response: This is an artifact of the disorder of the oxygen atoms bonded to the methyl groups.
PLAT772_ALERT_2_A Suspect O-H Bond in CIF:      O3AB   -H9AC    ..       1.30 Ang.
Author Response: This is an artifact of the disorder of the oxygen atoms bonded to the methyl groups.
PLAT772_ALERT_2_A Suspect O-H Bond in CIF:      O4AB   -H10C    ..       1.33 Ang.
Author Response: This is an artifact of the disorder of the oxygen atoms bonded to the methyl groups.

Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.17 Sigma PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9A PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O3AB PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl4A .. O3B .. 3.10 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl4B .. O1AB .. 3.15 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 15 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.14 Ratio
4 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990b); software used to prepare material for publication: SHELXTL/PC and SHELXL97.

2-Chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphate top
Crystal data top
C10H9Cl4O4PZ = 4
Mr = 365.96F(000) = 736
Triclinic, P1Dx = 1.678 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9371 (5) ÅCell parameters from 100 reflections
b = 14.0202 (11) Åθ = 10.0–21.0°
c = 15.1206 (12) ŵ = 0.93 mm1
α = 98.986 (5)°T = 295 K
β = 93.986 (6)°Block cut from larger crystal, colorless
γ = 90.256 (6)°0.58 × 0.53 × 0.32 mm
V = 1448.88 (19) Å3
Data collection top
Bruker P4
diffractometer
4239 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 25.0°, θmin = 2.7°
θ/2θ scansh = 18
Absorption correction: integration
(XSHELL; Bruker, 1999)
k = 1616
Tmin = 0.58, Tmax = 0.74l = 1717
6417 measured reflections3 standard reflections every 100 reflections
5061 independent reflections intensity decay: 3.9%
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0427P)2 + 1.5005P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
5061 reflectionsΔρmax = 0.41 e Å3
372 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0019 (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*/UeqOcc. (<1)
Cl1A0.29804 (17)0.43391 (8)0.58936 (7)0.0658 (3)
Cl2A0.94006 (12)0.38073 (8)0.75885 (6)0.0581 (3)
Cl4A0.81913 (16)0.38972 (8)1.10467 (6)0.0624 (3)
Cl5A0.36620 (15)0.37047 (8)1.05535 (6)0.0590 (3)
P1A0.45201 (13)0.18323 (6)0.66059 (6)0.0404 (2)
O2A0.5450 (3)0.28809 (15)0.66127 (14)0.0380 (5)
O1AA0.2748 (9)0.1849 (4)0.7044 (4)0.0729 (18)0.594 (5)
O3AA0.6102 (8)0.1259 (3)0.7034 (3)0.0674 (16)0.594 (5)
O4AA0.4488 (6)0.1424 (3)0.5590 (3)0.0494 (12)0.594 (5)
O1AB0.3990 (12)0.1642 (5)0.7485 (5)0.059 (2)0.406 (5)
O3AB0.6109 (8)0.1164 (4)0.6152 (4)0.0445 (17)0.406 (5)
O4AB0.2807 (8)0.1728 (5)0.5904 (4)0.0547 (19)0.406 (5)
C1A0.5790 (4)0.3705 (2)0.8168 (2)0.0341 (6)
C2A0.7781 (4)0.3770 (2)0.8408 (2)0.0390 (7)
C3A0.8504 (5)0.3837 (2)0.9286 (2)0.0440 (8)
H3A0.98300.38880.94290.053*
C4A0.7253 (5)0.3826 (2)0.9951 (2)0.0424 (8)
C5A0.5270 (5)0.3749 (2)0.9736 (2)0.0401 (7)
C6A0.4566 (4)0.3686 (2)0.8849 (2)0.0380 (7)
H6A0.32400.36300.87080.046*
C7A0.4988 (4)0.3676 (2)0.7234 (2)0.0340 (7)
C8A0.3956 (5)0.4380 (2)0.6977 (2)0.0421 (8)
H8A0.37440.49220.73960.050*
C9A0.7961 (7)0.1091 (4)0.6671 (4)0.0843 (15)
H9AA0.87230.07030.70280.126*0.594 (5)
H9AB0.86130.16980.66780.126*0.594 (5)
H9AC0.77840.07600.60650.126*0.594 (5)
H9AD0.87970.06640.63210.126*0.406 (5)
H9AE0.85610.17190.68230.126*0.406 (5)
H9AF0.77300.08410.72110.126*0.406 (5)
C10A0.2982 (7)0.1670 (4)0.4959 (3)0.0745 (13)
H10A0.31800.13320.43700.112*0.594 (5)
H10B0.30180.23530.49530.112*0.594 (5)
H10C0.17480.14870.51360.112*0.594 (5)
H10D0.17240.16070.46480.112*0.406 (5)
H10E0.36130.22440.48460.112*0.406 (5)
H10F0.37360.11170.47520.112*0.406 (5)
Cl1B0.73932 (18)0.06666 (8)0.40238 (7)0.0682 (3)
Cl2B1.33037 (13)0.12445 (9)0.22898 (7)0.0665 (3)
Cl4B1.09331 (16)0.14379 (8)0.11064 (6)0.0618 (3)
Cl5B0.65548 (15)0.12346 (8)0.06428 (6)0.0617 (3)
P1B0.89232 (12)0.31276 (6)0.33664 (5)0.0382 (2)
O1B0.6932 (4)0.3157 (2)0.30124 (19)0.0610 (7)
O2B0.9755 (3)0.20603 (15)0.33087 (14)0.0387 (5)
O3B1.0321 (4)0.36908 (19)0.28766 (17)0.0576 (7)
O4B0.9426 (4)0.35324 (18)0.43774 (15)0.0507 (6)
C1B0.9493 (4)0.1286 (2)0.1737 (2)0.0358 (7)
C2B1.1401 (5)0.1302 (2)0.1499 (2)0.0413 (7)
C3B1.1807 (5)0.1336 (3)0.0624 (2)0.0463 (8)
H3B1.30850.13620.04790.056*
C4B1.0328 (5)0.1334 (2)0.0037 (2)0.0417 (7)
C5B0.8435 (5)0.1274 (2)0.0183 (2)0.0420 (7)
C6B0.8028 (5)0.1263 (2)0.1059 (2)0.0408 (7)
H6B0.67470.12390.12000.049*
C7B0.9009 (4)0.1293 (2)0.2679 (2)0.0363 (7)
C8B0.7993 (5)0.0610 (2)0.2937 (2)0.0449 (8)
H8B0.75840.00780.25170.054*
C9B1.2368 (7)0.3814 (4)0.3135 (4)0.0767 (13)
H9BA1.30170.40130.26520.115*
H9BB1.28860.32130.32640.115*
H9BC1.25560.42970.36590.115*
C10B0.8165 (8)0.3361 (4)0.5047 (3)0.0763 (13)
H10G0.81120.39320.54870.114*
H10H0.86440.28360.53330.114*
H10I0.68930.32000.47710.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0794 (7)0.0671 (6)0.0483 (5)0.0158 (5)0.0170 (5)0.0100 (5)
Cl2A0.0326 (4)0.0965 (7)0.0423 (5)0.0097 (4)0.0074 (3)0.0000 (5)
Cl4A0.0731 (7)0.0785 (7)0.0325 (4)0.0108 (5)0.0069 (4)0.0034 (4)
Cl5A0.0639 (6)0.0716 (6)0.0432 (5)0.0062 (5)0.0207 (4)0.0069 (4)
P1A0.0451 (5)0.0398 (5)0.0349 (4)0.0045 (4)0.0037 (4)0.0011 (3)
O2A0.0405 (12)0.0382 (12)0.0338 (11)0.0025 (9)0.0057 (9)0.0004 (9)
O1AA0.072 (4)0.067 (3)0.076 (4)0.023 (3)0.035 (3)0.012 (3)
O3AA0.094 (4)0.054 (3)0.055 (3)0.010 (3)0.008 (3)0.017 (2)
O4AA0.051 (3)0.055 (3)0.037 (2)0.0006 (19)0.0046 (18)0.0035 (18)
O1AB0.071 (5)0.059 (4)0.047 (4)0.015 (4)0.016 (4)0.006 (3)
O3AB0.040 (3)0.049 (3)0.041 (3)0.010 (3)0.003 (2)0.003 (3)
O4AB0.035 (3)0.061 (4)0.061 (4)0.006 (3)0.006 (3)0.007 (3)
C1A0.0308 (15)0.0344 (16)0.0356 (16)0.0019 (12)0.0005 (12)0.0022 (12)
C2A0.0318 (16)0.0462 (18)0.0367 (17)0.0018 (13)0.0044 (13)0.0011 (14)
C3A0.0360 (17)0.052 (2)0.0403 (18)0.0001 (15)0.0031 (14)0.0016 (15)
C4A0.050 (2)0.0436 (18)0.0310 (16)0.0071 (15)0.0015 (14)0.0007 (14)
C5A0.0466 (19)0.0389 (17)0.0350 (16)0.0024 (14)0.0105 (14)0.0031 (13)
C6A0.0308 (16)0.0431 (17)0.0394 (17)0.0024 (13)0.0047 (13)0.0030 (14)
C7A0.0292 (15)0.0375 (16)0.0337 (15)0.0051 (12)0.0051 (12)0.0005 (13)
C8A0.0402 (18)0.0465 (19)0.0367 (17)0.0000 (15)0.0031 (14)0.0005 (14)
C9A0.071 (3)0.081 (3)0.097 (4)0.027 (3)0.015 (3)0.013 (3)
C10A0.076 (3)0.086 (3)0.053 (2)0.006 (2)0.024 (2)0.002 (2)
Cl1B0.0947 (8)0.0611 (6)0.0518 (6)0.0150 (5)0.0307 (5)0.0073 (5)
Cl2B0.0315 (4)0.1125 (9)0.0526 (5)0.0088 (5)0.0013 (4)0.0054 (5)
Cl4B0.0745 (7)0.0731 (6)0.0398 (5)0.0091 (5)0.0196 (4)0.0080 (4)
Cl5B0.0550 (6)0.0819 (7)0.0446 (5)0.0092 (5)0.0088 (4)0.0038 (5)
P1B0.0375 (4)0.0412 (5)0.0341 (4)0.0007 (3)0.0023 (3)0.0029 (3)
O1B0.0453 (14)0.0642 (17)0.0662 (17)0.0114 (12)0.0157 (13)0.0037 (13)
O2B0.0364 (12)0.0408 (12)0.0373 (12)0.0004 (9)0.0033 (9)0.0037 (9)
O3B0.0686 (17)0.0577 (15)0.0491 (15)0.0129 (13)0.0016 (13)0.0188 (12)
O4B0.0506 (14)0.0614 (15)0.0357 (12)0.0015 (12)0.0009 (11)0.0047 (11)
C1B0.0360 (16)0.0326 (16)0.0383 (17)0.0004 (13)0.0054 (13)0.0031 (13)
C2B0.0311 (16)0.0494 (19)0.0418 (17)0.0004 (14)0.0026 (13)0.0024 (15)
C3B0.0350 (17)0.055 (2)0.049 (2)0.0002 (15)0.0131 (15)0.0045 (16)
C4B0.0490 (19)0.0378 (17)0.0385 (17)0.0027 (14)0.0107 (15)0.0034 (14)
C5B0.0416 (18)0.0429 (18)0.0393 (18)0.0063 (14)0.0009 (14)0.0014 (14)
C6B0.0314 (16)0.0457 (18)0.0440 (18)0.0024 (14)0.0040 (14)0.0023 (14)
C7B0.0309 (15)0.0368 (16)0.0401 (17)0.0033 (13)0.0035 (13)0.0027 (13)
C8B0.048 (2)0.0444 (19)0.0413 (18)0.0040 (15)0.0126 (15)0.0006 (15)
C9B0.062 (3)0.080 (3)0.091 (3)0.023 (2)0.010 (2)0.021 (3)
C10B0.091 (3)0.091 (3)0.046 (2)0.003 (3)0.023 (2)0.001 (2)
Geometric parameters (Å, º) top
Cl1A—C8A1.720 (3)C9A—H9AC0.96
Cl2A—C2A1.736 (3)C9A—H9AD0.96
Cl4A—C4A1.726 (3)C9A—H9AE0.96
Cl5A—C5A1.730 (3)C9A—H9AF0.96
P1A—O1AA1.436 (5)C10A—H10A0.96
P1A—O1AB1.467 (7)C10A—H10B0.96
P1A—O4AB1.528 (6)C10A—H10C0.96
P1A—O3AA1.530 (5)C10A—H10D0.96
P1A—O4AA1.553 (4)C10A—H10E0.96
P1A—O3AB1.574 (5)C10A—H10F0.96
P1A—O2A1.601 (2)Cl1B—C8B1.714 (3)
P1A—H3A5.83Cl2B—C2B1.730 (3)
P1A—H6A3.89Cl4B—C4B1.726 (3)
O2A—C7A1.395 (4)Cl5B—C5B1.736 (3)
O1AA—O1AB1.120 (9)P1B—O1B1.449 (3)
O1AA—O4AB1.710 (9)P1B—O3B1.545 (3)
O3AA—O3AB1.321 (7)P1B—O4B1.560 (2)
O3AA—C9A1.443 (7)P1B—O2B1.598 (2)
O3AA—O1AB1.712 (9)P1B—H3B5.65
O3AA—H9AF1.3053P1B—H6B4.07
O4AA—O4AB1.336 (7)O2B—C7B1.392 (4)
O4AA—C10A1.444 (6)O3B—C9B1.448 (5)
O4AA—O3AB1.445 (7)O4B—C10B1.430 (5)
O4AA—H10F1.3399C1B—C6B1.389 (4)
O3AB—C9A1.471 (7)C1B—C2B1.397 (4)
O3AB—H9AC1.3012C1B—C7B1.484 (4)
O4AB—C10A1.431 (8)C2B—C3B1.379 (5)
O4AB—H10C1.3263C3B—C4B1.382 (5)
C1A—C6A1.383 (4)C3B—H3B0.93
C1A—C2A1.402 (4)C4B—C5B1.382 (5)
C1A—C7A1.476 (4)C5B—C6B1.376 (5)
C2A—C3A1.375 (5)C6B—H6B0.93
C3A—C4A1.375 (5)C7B—C8B1.310 (5)
C3A—H3A0.93C8B—H8B0.93
C4A—C5A1.391 (5)C9B—H9BA0.96
C5A—C6A1.385 (4)C9B—H9BB0.96
C6A—H6A0.93C9B—H9BC0.96
C7A—C8A1.314 (5)C10B—H10G0.96
C8A—H8A0.93C10B—H10H0.96
C9A—H9AA0.96C10B—H10I0.96
C9A—H9AB0.96
O1AA—P1A—O1AB45.4 (3)O3AA—C9A—H9AC109.5
O1AA—P1A—O4AB70.4 (4)O3AB—C9A—H9AC60.5
O1AB—P1A—O4AB112.8 (4)H9AA—C9A—H9AC109.5
O1AA—P1A—O3AA113.0 (4)H9AB—C9A—H9AC109.5
O1AB—P1A—O3AA69.6 (4)O3AA—C9A—H9AD148.7
O4AB—P1A—O3AA142.7 (3)O3AB—C9A—H9AD109.7
O1AA—P1A—O4AA118.8 (3)H9AA—C9A—H9AD67.6
O1AB—P1A—O4AA145.0 (3)H9AB—C9A—H9AD100.4
O4AB—P1A—O4AA51.4 (3)H9AC—C9A—H9AD49.3
O3AA—P1A—O4AA104.0 (2)O3AA—C9A—H9AE101.6
O1AA—P1A—O3AB144.8 (3)O3AB—C9A—H9AE109.6
O1AB—P1A—O3AB116.3 (4)H9AA—C9A—H9AE103.5
O4AB—P1A—O3AB104.3 (3)H9AC—C9A—H9AE122.6
O3AA—P1A—O3AB50.3 (3)H9AD—C9A—H9AE109.5
O4AA—P1A—O3AB55.0 (3)O3AA—C9A—H9AF62.0
O1AA—P1A—O2A113.8 (2)O3AB—C9A—H9AF109.2
O1AB—P1A—O2A114.6 (3)H9AA—C9A—H9AF47.5
O4AB—P1A—O2A106.4 (3)H9AB—C9A—H9AF122.4
O3AA—P1A—O2A105.4 (2)H9AC—C9A—H9AF127.5
O4AA—P1A—O2A100.38 (18)H9AD—C9A—H9AF109.5
O3AB—P1A—O2A101.2 (2)H9AE—C9A—H9AF109.5
C7A—O2A—P1A121.93 (19)O4AB—C10A—O4AA55.4 (3)
O1AB—O1AA—P1A68.8 (5)O4AB—C10A—H10A153.7
O1AB—O1AA—O4AB122.3 (6)O4AA—C10A—H10A109.5
P1A—O1AA—O4AB57.3 (3)O4AB—C10A—H10B96.5
O3AB—O3AA—C9A64.1 (4)O4AA—C10A—H10B109.5
O3AB—O3AA—P1A66.6 (3)H10A—C10A—H10B109.5
C9A—O3AA—P1A122.7 (4)O4AB—C10A—H10C63.9
O3AB—O3AA—O1AB116.2 (5)O4AA—C10A—H10C109.5
C9A—O3AA—O1AB171.2 (5)H10A—C10A—H10C109.5
P1A—O3AA—O1AB53.5 (3)H10B—C10A—H10C109.5
O3AB—O3AA—H9AF99.5O4AB—C10A—H10D109.8
P1A—O3AA—H9AF163.2O4AA—C10A—H10D154.6
O1AB—O3AA—H9AF142.8H10A—C10A—H10D74.7
O4AB—O4AA—C10A61.8 (4)H10B—C10A—H10D91.6
O4AB—O4AA—O3AB123.5 (5)H10C—C10A—H10D48.1
C10A—O4AA—O3AB174.7 (5)O4AB—C10A—H10E109.4
O4AB—O4AA—P1A63.4 (3)O4AA—C10A—H10E95.5
C10A—O4AA—P1A121.5 (3)H10A—C10A—H10E92.4
O3AB—O4AA—P1A63.2 (3)H10C—C10A—H10E137.8
O4AB—O4AA—H10F94.7H10D—C10A—H10E109.5
O3AB—O4AA—H10F135.9O4AB—C10A—H10F109.2
P1A—O4AA—H10F157.9O4AA—C10A—H10F64.1
O1AA—O1AB—P1A65.8 (5)H10A—C10A—H10F47.5
O1AA—O1AB—O3AA120.2 (6)H10B—C10A—H10F137.7
P1A—O1AB—O3AA56.9 (3)H10C—C10A—H10F111.9
O3AA—O3AB—O4AA122.8 (5)H10D—C10A—H10F109.5
O3AA—O3AB—C9A62.0 (4)H10E—C10A—H10F109.5
O4AA—O3AB—C9A167.3 (6)O1B—P1B—O3B112.87 (17)
O3AA—O3AB—P1A63.1 (3)O1B—P1B—O4B118.41 (15)
O4AA—O3AB—P1A61.7 (3)O3B—P1B—O4B103.36 (14)
C9A—O3AB—P1A117.9 (4)O1B—P1B—O2B113.74 (14)
O3AA—O3AB—H9AC98.2O3B—P1B—O2B105.98 (14)
O4AA—O3AB—H9AC138.9O4B—P1B—O2B100.97 (13)
P1A—O3AB—H9AC157.7C7B—O2B—P1B122.36 (19)
O4AA—O4AB—C10A62.8 (4)C9B—O3B—P1B123.6 (3)
O4AA—O4AB—P1A65.3 (3)C10B—O4B—P1B120.9 (3)
C10A—O4AB—P1A124.2 (5)C6B—C1B—C2B117.8 (3)
O4AA—O4AB—O1AA114.7 (5)C6B—C1B—C7B120.1 (3)
C10A—O4AB—O1AA175.8 (5)C2B—C1B—C7B122.1 (3)
P1A—O4AB—O1AA52.3 (3)C3B—C2B—C1B120.8 (3)
O4AA—O4AB—H10C96.3C3B—C2B—Cl2B118.6 (3)
P1A—O4AB—H10C161.4C1B—C2B—Cl2B120.6 (3)
O1AA—O4AB—H10C143.5C2B—C3B—C4B120.4 (3)
C6A—C1A—C2A117.4 (3)C2B—C3B—H3B119.8
C6A—C1A—C7A120.1 (3)C4B—C3B—H3B119.8
C2A—C1A—C7A122.5 (3)C3B—C4B—C5B119.3 (3)
C3A—C2A—C1A121.9 (3)C3B—C4B—Cl4B118.1 (3)
C3A—C2A—Cl2A118.3 (3)C5B—C4B—Cl4B122.6 (3)
C1A—C2A—Cl2A119.8 (2)C6B—C5B—C4B120.2 (3)
C4A—C3A—C2A119.5 (3)C6B—C5B—Cl5B119.6 (3)
C4A—C3A—H3A120.2C4B—C5B—Cl5B120.1 (3)
C2A—C3A—H3A120.2C5B—C6B—C1B121.3 (3)
C3A—C4A—C5A120.2 (3)C5B—C6B—H6B119.3
C3A—C4A—Cl4A118.8 (3)C1B—C6B—H6B119.3
C5A—C4A—Cl4A121.0 (3)C8B—C7B—O2B119.8 (3)
C6A—C5A—C4A119.5 (3)C8B—C7B—C1B123.5 (3)
C6A—C5A—Cl5A119.1 (3)O2B—C7B—C1B116.6 (3)
C4A—C5A—Cl5A121.3 (3)C7B—C8B—Cl1B122.0 (3)
C1A—C6A—C5A121.5 (3)C7B—C8B—H8B119.0
C1A—C6A—H6A119.2Cl1B—C8B—H8B119.0
C5A—C6A—H6A119.2O3B—C9B—H9BA109.5
C8A—C7A—O2A120.5 (3)O3B—C9B—H9BB109.5
C8A—C7A—C1A122.4 (3)H9BA—C9B—H9BB109.5
O2A—C7A—C1A117.0 (3)O3B—C9B—H9BC109.5
C7A—C8A—Cl1A122.6 (3)H9BA—C9B—H9BC109.5
C7A—C8A—H8A118.7H9BB—C9B—H9BC109.5
Cl1A—C8A—H8A118.7O4B—C10B—H10G109.5
O3AA—C9A—O3AB53.9 (3)O4B—C10B—H10H109.5
O3AA—C9A—H9AA109.5H10G—C10B—H10H109.5
O3AB—C9A—H9AA145.2O4B—C10B—H10I109.5
O3AA—C9A—H9AB109.5H10G—C10B—H10I109.5
O3AB—C9A—H9AB105.1H10H—C10B—H10I109.5
H9AA—C9A—H9AB109.5
O1AA—P1A—O2A—C7A21.1 (4)O4AA—P1A—O3AB—C9A165.6 (6)
O1AB—P1A—O2A—C7A28.9 (5)O2A—P1A—O3AB—C9A70.7 (5)
O4AB—P1A—O2A—C7A96.4 (3)O3AB—O4AA—O4AB—C10A179.5 (5)
O3AA—P1A—O2A—C7A103.2 (3)P1A—O4AA—O4AB—C10A158.8 (4)
O4AA—P1A—O2A—C7A149.0 (3)C10A—O4AA—O4AB—P1A158.8 (4)
O3AB—P1A—O2A—C7A154.9 (3)O3AB—O4AA—O4AB—P1A20.7 (5)
O4AB—P1A—O1AA—O1AB158.4 (6)C10A—O4AA—O4AB—O1AA176.3 (6)
O3AA—P1A—O1AA—O1AB18.3 (5)O3AB—O4AA—O4AB—O1AA3.2 (7)
O4AA—P1A—O1AA—O1AB140.5 (5)P1A—O4AA—O4AB—O1AA17.5 (3)
O3AB—P1A—O1AA—O1AB71.3 (7)O1AA—P1A—O4AB—O4AA159.8 (4)
O2A—P1A—O1AA—O1AB101.7 (5)O1AB—P1A—O4AB—O4AA143.3 (4)
O1AB—P1A—O1AA—O4AB158.4 (6)O3AA—P1A—O4AB—O4AA57.4 (6)
O3AA—P1A—O1AA—O4AB140.1 (3)O3AB—P1A—O4AB—O4AA16.2 (4)
O4AA—P1A—O1AA—O4AB17.9 (4)O2A—P1A—O4AB—O4AA90.3 (3)
O3AB—P1A—O1AA—O4AB87.1 (6)O1AA—P1A—O4AB—C10A177.3 (7)
O2A—P1A—O1AA—O4AB99.9 (3)O1AB—P1A—O4AB—C10A166.2 (6)
O1AA—P1A—O3AA—O3AB143.3 (4)O3AA—P1A—O4AB—C10A80.3 (8)
O1AB—P1A—O3AA—O3AB157.1 (5)O4AA—P1A—O4AB—C10A22.9 (4)
O4AB—P1A—O3AA—O3AB55.9 (6)O3AB—P1A—O4AB—C10A39.1 (6)
O4AA—P1A—O3AA—O3AB13.2 (4)O2A—P1A—O4AB—C10A67.4 (6)
O2A—P1A—O3AA—O3AB91.9 (3)O1AB—P1A—O4AB—O1AA16.5 (4)
O1AA—P1A—O3AA—C9A175.8 (4)O3AA—P1A—O4AB—O1AA102.4 (5)
O1AB—P1A—O3AA—C9A170.4 (6)O4AA—P1A—O4AB—O1AA159.8 (4)
O4AB—P1A—O3AA—C9A88.4 (7)O3AB—P1A—O4AB—O1AA143.6 (3)
O4AA—P1A—O3AA—C9A45.7 (5)O2A—P1A—O4AB—O1AA109.9 (3)
O3AB—P1A—O3AA—C9A32.5 (4)O1AB—O1AA—O4AB—O4AA3.8 (9)
O2A—P1A—O3AA—C9A59.4 (5)P1A—O1AA—O4AB—O4AA20.2 (4)
O1AA—P1A—O3AA—O1AB13.8 (4)O1AB—O1AA—O4AB—P1A24.0 (6)
O4AB—P1A—O3AA—O1AB101.2 (6)C6A—C1A—C2A—C3A1.6 (5)
O4AA—P1A—O3AA—O1AB143.9 (3)C7A—C1A—C2A—C3A177.3 (3)
O3AB—P1A—O3AA—O1AB157.1 (5)C6A—C1A—C2A—Cl2A179.5 (2)
O2A—P1A—O3AA—O1AB111.0 (3)C7A—C1A—C2A—Cl2A0.6 (4)
O1AA—P1A—O4AA—O4AB21.8 (5)C1A—C2A—C3A—C4A0.9 (5)
O1AB—P1A—O4AA—O4AB73.9 (8)Cl2A—C2A—C3A—C4A178.9 (3)
O3AA—P1A—O4AA—O4AB148.3 (4)C2A—C3A—C4A—C5A0.0 (5)
O3AB—P1A—O4AA—O4AB160.7 (5)C2A—C3A—C4A—Cl4A179.3 (3)
O2A—P1A—O4AA—O4AB102.8 (4)C3A—C4A—C5A—C6A0.3 (5)
O1AA—P1A—O4AA—C10A43.8 (5)Cl4A—C4A—C5A—C6A179.5 (3)
O1AB—P1A—O4AA—C10A95.9 (8)C3A—C4A—C5A—Cl5A178.4 (3)
O4AB—P1A—O4AA—C10A22.0 (4)Cl4A—C4A—C5A—Cl5A0.8 (4)
O3AA—P1A—O4AA—C10A170.3 (4)C2A—C1A—C6A—C5A1.3 (5)
O3AB—P1A—O4AA—C10A177.3 (5)C7A—C1A—C6A—C5A177.6 (3)
O2A—P1A—O4AA—C10A80.8 (4)C4A—C5A—C6A—C1A0.4 (5)
O1AA—P1A—O4AA—O3AB138.9 (4)Cl5A—C5A—C6A—C1A179.1 (2)
O1AB—P1A—O4AA—O3AB86.7 (7)P1A—O2A—C7A—C8A110.1 (3)
O4AB—P1A—O4AA—O3AB160.7 (5)P1A—O2A—C7A—C1A72.9 (3)
O3AA—P1A—O4AA—O3AB12.4 (4)C6A—C1A—C7A—C8A65.9 (4)
O2A—P1A—O4AA—O3AB96.5 (3)C2A—C1A—C7A—C8A112.9 (4)
O4AB—O1AA—O1AB—P1A21.5 (5)C6A—C1A—C7A—O2A117.1 (3)
P1A—O1AA—O1AB—O3AA17.4 (5)C2A—C1A—C7A—O2A64.1 (4)
O4AB—O1AA—O1AB—O3AA4.1 (10)O2A—C7A—C8A—Cl1A4.4 (4)
O4AB—P1A—O1AB—O1AA22.1 (6)C1A—C7A—C8A—Cl1A178.7 (2)
O3AA—P1A—O1AB—O1AA162.0 (5)P1A—O3AA—C9A—O3AB33.2 (4)
O4AA—P1A—O1AB—O1AA76.7 (8)O4AA—O3AB—C9A—O3AA115 (2)
O3AB—P1A—O1AB—O1AA142.5 (4)P1A—O3AB—C9A—O3AA30.4 (4)
O2A—P1A—O1AB—O1AA99.9 (4)P1A—O4AB—C10A—O4AA23.4 (4)
O1AA—P1A—O1AB—O3AA162.0 (5)P1A—O4AA—C10A—O4AB22.3 (4)
O4AB—P1A—O1AB—O3AA139.9 (4)O1B—P1B—O2B—C7B25.0 (3)
O4AA—P1A—O1AB—O3AA85.4 (6)O3B—P1B—O2B—C7B99.6 (2)
O3AB—P1A—O1AB—O3AA19.5 (4)O4B—P1B—O2B—C7B152.9 (2)
O2A—P1A—O1AB—O3AA98.1 (3)O1B—P1B—O3B—C9B176.6 (3)
O3AB—O3AA—O1AB—O1AA4.4 (9)O4B—P1B—O3B—C9B47.4 (4)
P1A—O3AA—O1AB—O1AA19.0 (5)O2B—P1B—O3B—C9B58.3 (3)
O3AB—O3AA—O1AB—P1A23.5 (5)O1B—P1B—O4B—C10B40.0 (4)
C9A—O3AA—O3AB—O4AA166.3 (6)O3B—P1B—O4B—C10B165.6 (3)
P1A—O3AA—O3AB—O4AA16.4 (5)O2B—P1B—O4B—C10B84.9 (3)
O1AB—O3AA—O3AB—O4AA3.9 (8)C6B—C1B—C2B—C3B2.8 (5)
P1A—O3AA—O3AB—C9A149.9 (4)C7B—C1B—C2B—C3B177.2 (3)
O1AB—O3AA—O3AB—C9A170.3 (5)C6B—C1B—C2B—Cl2B175.4 (2)
C9A—O3AA—O3AB—P1A149.9 (4)C7B—C1B—C2B—Cl2B4.6 (4)
O1AB—O3AA—O3AB—P1A20.4 (4)C1B—C2B—C3B—C4B1.5 (5)
O4AB—O4AA—O3AB—O3AA4.1 (9)Cl2B—C2B—C3B—C4B176.8 (3)
P1A—O4AA—O3AB—O3AA16.7 (5)C2B—C3B—C4B—C5B1.5 (5)
O4AB—O4AA—O3AB—C9A112 (2)C2B—C3B—C4B—Cl4B176.9 (3)
P1A—O4AA—O3AB—C9A92 (2)C3B—C4B—C5B—C6B3.1 (5)
O4AB—O4AA—O3AB—P1A20.7 (5)Cl4B—C4B—C5B—C6B175.3 (3)
O1AA—P1A—O3AB—O3AA72.8 (7)C3B—C4B—C5B—Cl5B178.1 (3)
O1AB—P1A—O3AB—O3AA24.0 (5)Cl4B—C4B—C5B—Cl5B3.5 (4)
O4AB—P1A—O3AB—O3AA148.9 (4)C4B—C5B—C6B—C1B1.7 (5)
O4AA—P1A—O3AB—O3AA164.3 (5)Cl5B—C5B—C6B—C1B179.5 (3)
O2A—P1A—O3AB—O3AA100.8 (3)C2B—C1B—C6B—C5B1.2 (5)
O1AA—P1A—O3AB—O4AA91.6 (6)C7B—C1B—C6B—C5B178.8 (3)
O1AB—P1A—O3AB—O4AA140.3 (4)P1B—O2B—C7B—C8B108.7 (3)
O4AB—P1A—O3AB—O4AA15.5 (4)P1B—O2B—C7B—C1B73.5 (3)
O3AA—P1A—O3AB—O4AA164.3 (5)C6B—C1B—C7B—C8B59.2 (4)
O2A—P1A—O3AB—O4AA94.9 (3)C2B—C1B—C7B—C8B120.8 (4)
O1AA—P1A—O3AB—C9A102.9 (7)C6B—C1B—C7B—O2B123.1 (3)
O1AB—P1A—O3AB—C9A54.1 (6)C2B—C1B—C7B—O2B56.9 (4)
O4AB—P1A—O3AB—C9A179.0 (5)O2B—C7B—C8B—Cl1B4.7 (5)
O3AA—P1A—O3AB—C9A30.1 (4)C1B—C7B—C8B—Cl1B177.7 (2)
Selected Geometric Parameters (Å,°) top
Bond Molecule ADistanceBond Molecule BDistance
Cl1A—C8A1.720 (3)Cl1B—C8B1.714 (3)
Cl2A—C2A1.736 (3)Cl2B—C2B1.730 (3)
Cl4A—C4A1.726 (3)Cl4B—C4B1.726 (3)
Cl5A—C5A1.730 (3)Cl5B—C5B1.736 (3)
P1A—O1AA1.436 (5)P1B—O1B1.449 (3)
P1A—O1AB1.467 (7)
P1A—O2A1.601 (2)P1B—O2B1.598 (2)
P1A—O3AA1.530 (5)P1B—O3B1.545 (3)
P1A—O3AB1.574 (5)
P1A—O4AA1.553 (4)P1B—O4B1.560 (2)
P1A—O4AB1.528 (6)
O2A—C7A1.395 (4)O2B—C7B1.392 (4)
P1A···H3A5.83P1B···H3B5.65
P1A···H6A3.89P1B···H6B4.07
P1A···ring center4.38P1B···ring center4.35
Atoms in Molecule AAngleAtoms in Molecule BAngle
O1AA—P1A—O2A113.8 (2)O1B P1B O2B113.74 (14)
O1AB—P1A—O2A114.6 (3)
O1AA—P1A—O3AA113.0 (4)O1B P1B O3B112.87 (17)
O1AB—P1A—O3AB116.3 (4)
O1AA—P1A—O4AA118.8 (3)O1B P1B O4B118.41 (15)
O1AB—P1A—O4AB112.8 (4)
O2A—P1A—O3AA105.4 (2)O2B P1B O3B105.98 (14)
O2A—P1A—O3AB101.2 (2)
O2A—P1A—O4AA100.38 (18)O2B P1B O4B100.97 (13)
O2A—P1A—O4AB106.4 (3)
O3AA—P1A—O4AA104.0 (2)O3B P1B O4B103.36 (14)
O3AB—P1A—O4AB104.3 (3)
O1AA-P1A-O2A-C7A21.1 (4)O1B-P1B-O2B-C7B25.0 (3)
O1AB-P1A-O2A-C7A-28.9 (5)
O3AA-P1A-O2A-C7A-103.2 (3)O3B-P1B-O2B-C7B-99.6 (2)
O3AB-P1A-O2A-C7A-154.9 (3)
O4AA-P1A-O2A-C7A149.0 (3)O4B-P1B-O2B-C7B152.9 (2)
O4AB-P1A-O2A-C7A96.4 (3)
P1A-O2A-C7A-C1A72.9 (3)P1B-O2B-C7B-C1B73.5 (3)
C2A-C1A-C7A-O2A64.1 (4)C2B-C1B-C7B-O2B56.9 (4)
C2A-C1A-C7A-C8A-112.9 (4)C2B-C1B-C7B-C8B-120.8 (4)
C1A-C7A-C8A-Cl1A-178.7 (2)C1B-C7B-C8B-Cl1B-177.7 (3)
Close Chlorine···Oxygen and H···Cl Interactions (Å, °). top
InteractionDistance
O1AA···Cl4Bi3.274 (6)
O1AB···Cl4Bi3.151 (7)
O3AA···Cl5Bii 3.510 (5)
O3AB···Cl1B3.367 (6)
O4AA···Cl1B3.270 (4)
O4AB···Cl1Biii3.378 (7)
O1B···Cl4Aiv3.463 (3)
O3B···Cl4Aiv3.100 (3)
D—H···AD—HH···AD···AD—H···A
C3A—H3A···Cl5Av0.933.093.959 (4)157
C6A—H6A···Cl2Avi0.933.093.957 (3)156
C3B—H3B···Cl5Bv0.933.033.916 (4)160
C6B—H6B···Cl2Bvi0.932.993.882 (3)160
Symmetry codes: (i) x - 1, y, 1 + z; (ii) x, y, 1 + z; (iii) 1 - x, -y, 1 - z; (iv) x, y, z - 1; (v) 1 + x, y, z; (vi) x - 1, y, z
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds