2-{(2-Chloro­phen­yl)[(2,4-dichloro­phen­oxy)acet­oxy]meth­yl}-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one

In the title compound, C₂₀H₂₀Cl₃O₆P, all bond lengths and angles are normal. The P atom is in a distorted tetra­hedral configuration. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.051
• wR factor = 0.140
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18

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

   1 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
   1 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

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 1997); software used to prepare material for publication: SHELXTL.

2-{(2-Chlorophenyl)[(2,4-dichlorophenoxy)acetoxy]methyl]-5,5-dimethyl- 1,3,2-dioxaphosphinan-2-one

Crystal data

C20H20Cl3O6P	Z = 2
Mr = 493.68	F(000) = 508
Triclinic, P1	Dx = 1.428 Mg m^−3
a = 8.8627 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4972 (9) Å	Cell parameters from 5907 reflections
c = 13.3624 (11) Å	θ = 2.4–27.5°
α = 79.834 (1)°	µ = 0.50 mm^−1
β = 83.707 (1)°	T = 298 K
γ = 69.936 (1)°	Block, colourless
V = 1147.75 (16) Å^3	0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 27.0°, θmin = 2.1°
φ and ω scans	h = −11→11
12883 measured reflections	k = −13→13
4976 independent reflections	l = −17→17

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0677P)^2 + 0.5055P] where P = (Fo^2 + 2Fc^2)/3
4976 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.60 e Å^−3
0 restraints	Δρmin = −0.52 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	0.8210 (3)	−0.0529 (2)	1.25617 (18)	0.0518 (5)
C2	0.8484 (3)	−0.0036 (2)	1.14479 (18)	0.0563 (5)
H2A	0.9618	−0.0409	1.1253	0.068*
H2B	0.7893	−0.0371	1.1046	0.068*
C3	0.6420 (3)	0.0048 (2)	1.28438 (18)	0.0506 (5)
H3A	0.5837	−0.0325	1.2466	0.061*
H3B	0.6230	−0.0240	1.3563	0.061*
C4	0.9197 (3)	−0.0111 (3)	1.3218 (2)	0.0691 (7)
H4A	1.0310	−0.0430	1.2989	0.104*
H4B	0.9077	−0.0509	1.3914	0.104*
H4C	0.8830	0.0870	1.3168	0.104*
C5	0.8668 (3)	−0.2095 (3)	1.2705 (3)	0.0793 (8)
H5A	0.8040	−0.2344	1.2280	0.119*
H5B	0.8460	−0.2429	1.3405	0.119*
H5C	0.9790	−0.2493	1.2521	0.119*
C6	0.4877 (3)	0.2354 (2)	1.06897 (16)	0.0457 (4)
H6	0.4931	0.1411	1.0669	0.055*
C7	0.3164 (2)	0.3218 (2)	1.09126 (16)	0.0473 (5)
C8	0.2686 (3)	0.4636 (2)	1.06727 (18)	0.0547 (5)
H8	0.3428	0.5047	1.0360	0.066*
C9	0.1137 (3)	0.5445 (3)	1.0888 (2)	0.0666 (7)
H9	0.0840	0.6394	1.0720	0.080*
C10	0.0021 (3)	0.4851 (3)	1.1355 (2)	0.0732 (7)
H10	−0.1023	0.5400	1.1508	0.088*
C11	0.0450 (3)	0.3458 (3)	1.1593 (2)	0.0736 (7)
H11	−0.0299	0.3053	1.1904	0.088*
C12	0.2007 (3)	0.2657 (3)	1.1367 (2)	0.0601 (6)
C13	0.5199 (3)	0.2580 (2)	0.88784 (17)	0.0502 (5)
C14	0.6136 (3)	0.3116 (3)	0.80044 (18)	0.0613 (6)
H14A	0.5643	0.4103	0.7844	0.074*
H14B	0.7224	0.2926	0.8198	0.074*
C15	0.5067 (3)	0.3149 (2)	0.64174 (16)	0.0528 (5)
C16	0.5239 (3)	0.2476 (3)	0.55833 (17)	0.0584 (6)
C17	0.4205 (3)	0.3008 (3)	0.48011 (19)	0.0716 (7)
H17	0.4332	0.2547	0.4248	0.086*
C18	0.2998 (4)	0.4218 (4)	0.4850 (2)	0.0776 (8)
C19	0.2792 (4)	0.4913 (3)	0.5658 (3)	0.0777 (8)
H19	0.1962	0.5743	0.5676	0.093*
C20	0.3831 (3)	0.4373 (3)	0.6455 (2)	0.0660 (6)
H20	0.3690	0.4837	0.7009	0.079*
Cl1	0.25117 (9)	0.08788 (8)	1.16662 (9)	0.1031 (3)
Cl2	0.67788 (10)	0.09347 (10)	0.55291 (6)	0.0907 (3)
Cl3	0.17039 (14)	0.48871 (15)	0.38576 (8)	0.1334 (5)
O1	0.79677 (18)	0.14560 (16)	1.12283 (12)	0.0549 (4)
O2	0.58046 (17)	0.15395 (15)	1.26288 (11)	0.0502 (3)
O3	0.6200 (2)	0.37318 (17)	1.17054 (14)	0.0618 (4)
O4	0.55463 (18)	0.28946 (16)	0.97376 (11)	0.0508 (4)
O5	0.4318 (2)	0.1953 (2)	0.88502 (15)	0.0749 (5)
O6	0.6185 (2)	0.25048 (19)	0.71329 (12)	0.0670 (5)
P1	0.62569 (6)	0.23552 (5)	1.16119 (4)	0.04461 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0429 (11)	0.0503 (12)	0.0590 (12)	−0.0130 (9)	−0.0010 (9)	−0.0057 (9)
C2	0.0486 (12)	0.0574 (13)	0.0591 (13)	−0.0113 (10)	0.0043 (10)	−0.0158 (10)
C3	0.0452 (11)	0.0499 (11)	0.0563 (12)	−0.0179 (9)	−0.0004 (9)	−0.0041 (9)
C4	0.0516 (13)	0.093 (2)	0.0637 (15)	−0.0254 (13)	−0.0090 (11)	−0.0078 (13)
C5	0.0650 (16)	0.0514 (14)	0.107 (2)	−0.0073 (12)	0.0000 (15)	−0.0017 (14)
C6	0.0499 (11)	0.0453 (10)	0.0483 (11)	−0.0229 (9)	−0.0031 (9)	−0.0091 (8)
C7	0.0461 (11)	0.0522 (11)	0.0486 (11)	−0.0208 (9)	−0.0084 (9)	−0.0078 (9)
C8	0.0553 (12)	0.0527 (12)	0.0612 (13)	−0.0216 (10)	−0.0078 (10)	−0.0109 (10)
C9	0.0633 (15)	0.0575 (14)	0.0784 (17)	−0.0107 (11)	−0.0192 (13)	−0.0183 (12)
C10	0.0471 (13)	0.087 (2)	0.0840 (18)	−0.0108 (13)	−0.0089 (12)	−0.0295 (15)
C11	0.0478 (13)	0.092 (2)	0.0841 (19)	−0.0303 (14)	−0.0022 (12)	−0.0084 (15)
C12	0.0506 (12)	0.0605 (14)	0.0732 (15)	−0.0258 (11)	−0.0079 (11)	−0.0024 (11)
C13	0.0456 (11)	0.0532 (12)	0.0531 (12)	−0.0112 (9)	−0.0078 (9)	−0.0187 (9)
C14	0.0614 (14)	0.0801 (17)	0.0485 (12)	−0.0248 (12)	−0.0020 (10)	−0.0226 (11)
C15	0.0534 (12)	0.0618 (13)	0.0444 (11)	−0.0216 (10)	−0.0009 (9)	−0.0067 (9)
C16	0.0549 (13)	0.0767 (16)	0.0439 (11)	−0.0221 (11)	0.0032 (9)	−0.0128 (10)
C17	0.0703 (17)	0.104 (2)	0.0436 (12)	−0.0332 (16)	−0.0029 (11)	−0.0101 (13)
C18	0.0716 (17)	0.100 (2)	0.0573 (15)	−0.0339 (16)	−0.0163 (13)	0.0178 (15)
C19	0.0648 (16)	0.0639 (16)	0.093 (2)	−0.0157 (13)	−0.0101 (15)	0.0103 (15)
C20	0.0680 (15)	0.0606 (14)	0.0698 (16)	−0.0214 (12)	−0.0004 (12)	−0.0119 (12)
Cl1	0.0676 (4)	0.0678 (4)	0.1725 (9)	−0.0387 (4)	−0.0034 (5)	0.0176 (5)
Cl2	0.0755 (5)	0.1106 (6)	0.0765 (5)	−0.0016 (4)	−0.0033 (4)	−0.0494 (4)
Cl3	0.1087 (8)	0.1787 (12)	0.0902 (6)	−0.0345 (7)	−0.0480 (6)	0.0385 (7)
O1	0.0444 (8)	0.0587 (9)	0.0581 (9)	−0.0179 (7)	0.0049 (7)	−0.0025 (7)
O2	0.0452 (8)	0.0507 (8)	0.0499 (8)	−0.0102 (6)	0.0032 (6)	−0.0104 (6)
O3	0.0675 (10)	0.0511 (9)	0.0750 (11)	−0.0247 (8)	−0.0180 (8)	−0.0118 (8)
O4	0.0569 (9)	0.0614 (9)	0.0447 (8)	−0.0302 (7)	−0.0016 (6)	−0.0142 (6)
O5	0.0844 (13)	0.0937 (14)	0.0697 (11)	−0.0503 (11)	−0.0090 (9)	−0.0264 (10)
O6	0.0678 (11)	0.0780 (12)	0.0492 (9)	−0.0070 (9)	−0.0103 (8)	−0.0245 (8)
P1	0.0431 (3)	0.0446 (3)	0.0492 (3)	−0.0170 (2)	−0.0041 (2)	−0.0089 (2)

Geometric parameters (Å, º)

C1—C2	1.509 (3)	C10—C11	1.366 (4)
C1—C4	1.515 (3)	C10—H10	0.9300
C1—C3	1.522 (3)	C11—C12	1.380 (4)
C1—C5	1.534 (3)	C11—H11	0.9300
C2—O1	1.457 (3)	C12—Cl1	1.746 (3)
C2—H2A	0.9700	C13—O5	1.189 (3)
C2—H2B	0.9700	C13—O4	1.343 (2)
C3—O2	1.456 (3)	C13—C14	1.499 (3)
C3—H3A	0.9700	C14—O6	1.415 (3)
C3—H3B	0.9700	C14—H14A	0.9700
C4—H4A	0.9600	C14—H14B	0.9700
C4—H4B	0.9600	C15—O6	1.369 (3)
C4—H4C	0.9600	C15—C20	1.378 (4)
C5—H5A	0.9600	C15—C16	1.390 (3)
C5—H5B	0.9600	C16—C17	1.377 (4)
C5—H5C	0.9600	C16—Cl2	1.729 (3)
C6—O4	1.450 (2)	C17—C18	1.358 (4)
C6—C7	1.506 (3)	C17—H17	0.9300
C6—P1	1.829 (2)	C18—C19	1.370 (5)
C6—H6	0.9800	C18—Cl3	1.738 (3)
C7—C12	1.385 (3)	C19—C20	1.395 (4)
C7—C8	1.388 (3)	C19—H19	0.9300
C8—C9	1.374 (3)	C20—H20	0.9300
C8—H8	0.9300	O1—P1	1.5719 (16)
C9—C10	1.380 (4)	O2—P1	1.5639 (16)
C9—H9	0.9300	O3—P1	1.4555 (16)
C2—C1—C4	111.3 (2)	C11—C10—H10	120.0
C2—C1—C3	108.25 (18)	C9—C10—H10	120.0
C4—C1—C3	111.4 (2)	C10—C11—C12	119.3 (3)
C2—C1—C5	108.0 (2)	C10—C11—H11	120.4
C4—C1—C5	110.5 (2)	C12—C11—H11	120.4
C3—C1—C5	107.25 (19)	C11—C12—C7	122.2 (2)
O1—C2—C1	111.71 (18)	C11—C12—Cl1	118.2 (2)
O1—C2—H2A	109.3	C7—C12—Cl1	119.56 (19)
C1—C2—H2A	109.3	O5—C13—O4	124.1 (2)
O1—C2—H2B	109.3	O5—C13—C14	127.5 (2)
C1—C2—H2B	109.3	O4—C13—C14	108.39 (18)
H2A—C2—H2B	107.9	O6—C14—C13	111.2 (2)
O2—C3—C1	112.28 (17)	O6—C14—H14A	109.4
O2—C3—H3A	109.1	C13—C14—H14A	109.4
C1—C3—H3A	109.1	O6—C14—H14B	109.4
O2—C3—H3B	109.1	C13—C14—H14B	109.4
C1—C3—H3B	109.1	H14A—C14—H14B	108.0
H3A—C3—H3B	107.9	O6—C15—C20	126.2 (2)
C1—C4—H4A	109.5	O6—C15—C16	115.0 (2)
C1—C4—H4B	109.5	C20—C15—C16	118.8 (2)
H4A—C4—H4B	109.5	C17—C16—C15	121.4 (3)
C1—C4—H4C	109.5	C17—C16—Cl2	119.3 (2)
H4A—C4—H4C	109.5	C15—C16—Cl2	119.30 (19)
H4B—C4—H4C	109.5	C18—C17—C16	119.0 (3)
C1—C5—H5A	109.5	C18—C17—H17	120.5
C1—C5—H5B	109.5	C16—C17—H17	120.5
H5A—C5—H5B	109.5	C17—C18—C19	121.4 (3)
C1—C5—H5C	109.5	C17—C18—Cl3	118.7 (3)
H5A—C5—H5C	109.5	C19—C18—Cl3	119.9 (3)
H5B—C5—H5C	109.5	C18—C19—C20	119.8 (3)
O4—C6—C7	112.02 (17)	C18—C19—H19	120.1
O4—C6—P1	102.43 (12)	C20—C19—H19	120.1
C7—C6—P1	113.01 (14)	C15—C20—C19	119.7 (3)
O4—C6—H6	109.7	C15—C20—H20	120.2
C7—C6—H6	109.7	C19—C20—H20	120.2
P1—C6—H6	109.7	C2—O1—P1	120.84 (13)
C12—C7—C8	117.0 (2)	C3—O2—P1	122.31 (13)
C12—C7—C6	122.6 (2)	C13—O4—C6	117.24 (16)
C8—C7—C6	120.38 (19)	C15—O6—C14	119.55 (19)
C9—C8—C7	121.3 (2)	O3—P1—O2	113.75 (10)
C9—C8—H8	119.3	O3—P1—O1	112.20 (10)
C7—C8—H8	119.3	O2—P1—O1	106.84 (8)
C8—C9—C10	120.0 (3)	O3—P1—C6	112.63 (10)
C8—C9—H9	120.0	O2—P1—C6	105.53 (9)
C10—C9—H9	120.0	O1—P1—C6	105.26 (9)
C11—C10—C9	120.1 (2)
C4—C1—C2—O1	−62.7 (2)	C16—C17—C18—C19	0.1 (4)
C3—C1—C2—O1	60.0 (2)	C16—C17—C18—Cl3	179.7 (2)
C5—C1—C2—O1	175.83 (19)	C17—C18—C19—C20	−0.4 (5)
C2—C1—C3—O2	−57.3 (2)	Cl3—C18—C19—C20	179.9 (2)
C4—C1—C3—O2	65.4 (2)	O6—C15—C20—C19	179.3 (2)
C5—C1—C3—O2	−173.6 (2)	C16—C15—C20—C19	−0.5 (4)
O4—C6—C7—C12	143.0 (2)	C18—C19—C20—C15	0.6 (4)
P1—C6—C7—C12	−101.9 (2)	C1—C2—O1—P1	−49.7 (2)
O4—C6—C7—C8	−37.6 (3)	C1—C3—O2—P1	44.4 (2)
P1—C6—C7—C8	77.5 (2)	O5—C13—O4—C6	4.0 (3)
C12—C7—C8—C9	0.7 (3)	C14—C13—O4—C6	−174.38 (18)
C6—C7—C8—C9	−178.7 (2)	C7—C6—O4—C13	−82.1 (2)
C7—C8—C9—C10	0.2 (4)	P1—C6—O4—C13	156.53 (15)
C8—C9—C10—C11	−0.7 (4)	C20—C15—O6—C14	−0.9 (4)
C9—C10—C11—C12	0.4 (4)	C16—C15—O6—C14	178.9 (2)
C10—C11—C12—C7	0.6 (4)	C13—C14—O6—C15	94.0 (3)
C10—C11—C12—Cl1	−179.2 (2)	C3—O2—P1—O3	−152.57 (15)
C8—C7—C12—C11	−1.1 (4)	C3—O2—P1—O1	−28.21 (17)
C6—C7—C12—C11	178.3 (2)	C3—O2—P1—C6	83.47 (17)
C8—C7—C12—Cl1	178.69 (18)	C2—O1—P1—O3	155.95 (16)
C6—C7—C12—Cl1	−1.9 (3)	C2—O1—P1—O2	30.65 (18)
O5—C13—C14—O6	−14.7 (4)	C2—O1—P1—C6	−81.22 (17)
O4—C13—C14—O6	163.60 (19)	O4—C6—P1—O3	65.36 (15)
O6—C15—C16—C17	−179.7 (2)	C7—C6—P1—O3	−55.35 (18)
C20—C15—C16—C17	0.1 (4)	O4—C6—P1—O2	−169.98 (12)
O6—C15—C16—Cl2	0.5 (3)	C7—C6—P1—O2	69.31 (16)
C20—C15—C16—Cl2	−179.68 (19)	O4—C6—P1—O1	−57.18 (14)
C15—C16—C17—C18	0.1 (4)	C7—C6—P1—O1	−177.90 (14)
Cl2—C16—C17—C18	179.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl1	0.98	2.57	3.068 (2)	111
C17—H17···O2^i	0.93	2.60	3.463 (3)	155
C20—H20···O3^ii	0.93	2.50	3.417 (3)	167
C14—H14A···O3^ii	0.97	2.43	3.311 (3)	150
C8—H8···O4^ii	0.93	2.60	3.402 (3)	145
C5—H5A···O5^iii	0.96	2.59	3.488 (4)	156

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y, −z+2.