2-[Di­chloro­(phenoxy)­methyl]­phenyl di­chloro­phospho­nate

The reaction of phosphorus pentachloride with phenyl salicyl­ate yielded a compound of chemical formula C₁₃H₉Cl₄O₃P, which was originally thought to contain a P-O-C heterocycle. The true molecular structure has now been established by the determination of its crystal structure. There are two molecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.024
• wR factor = 0.065
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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

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Computing details

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

2-[Dichloro(phenoxy)methyl]phenyl dichlorophosphonate

Crystal data

C13H9Cl4O3P	Dx = 1.642 Mg m^−3
Mr = 385.97	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7002 reflections
a = 13.9369 (14) Å	θ = 2.5–28.5°
b = 19.0631 (17) Å	µ = 0.87 mm^−1
c = 23.503 (2) Å	T = 110 K
V = 6244.2 (10) Å^3	Block, colourless
Z = 16	0.24 × 0.20 × 0.20 mm
F(000) = 3104

Data collection

Bruker X8 APEX CCD area-detector diffractometer	6382 independent reflections
Radiation source: fine-focus sealed tube	5384 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.816, Tmax = 0.838	k = −19→23
107431 measured reflections	l = −29→29

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0307P)^2 + 3.3409P] where P = (Fo^2 + 2Fc^2)/3
6382 reflections	(Δ/σ)max = 0.002
379 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.26 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
Cl1	0.75390 (3)	0.20300 (2)	0.565583 (19)	0.02871 (10)
Cl2	0.58374 (3)	0.11310 (2)	0.617510 (18)	0.02633 (10)
Cl3	0.76534 (3)	0.03643 (2)	0.753757 (15)	0.01909 (9)
Cl4	0.75539 (3)	0.18660 (2)	0.731937 (15)	0.02028 (9)
Cl5	0.31866 (3)	0.89005 (3)	0.879373 (19)	0.03366 (11)
Cl6	0.48112 (3)	0.78728 (2)	0.92338 (2)	0.03242 (11)
Cl7	0.48864 (3)	0.80321 (2)	0.764846 (15)	0.02099 (9)
Cl8	0.50452 (3)	0.95255 (2)	0.740510 (16)	0.02132 (9)
O1	0.77363 (7)	0.07959 (6)	0.63294 (4)	0.0180 (2)
O2	0.71173 (9)	0.06158 (7)	0.52993 (5)	0.0325 (3)
O3	0.89223 (7)	0.12658 (6)	0.79330 (4)	0.0183 (2)
O4	0.51036 (7)	0.91373 (6)	0.86173 (4)	0.0186 (2)
O5	0.45603 (9)	0.92689 (7)	0.96723 (5)	0.0320 (3)
O6	0.62750 (7)	0.85858 (6)	0.70261 (4)	0.0180 (2)
P1	0.71219 (3)	0.10495 (2)	0.580778 (16)	0.01765 (9)
P2	0.44854 (3)	0.88836 (2)	0.914111 (17)	0.01955 (10)
C1	0.83809 (10)	0.11411 (8)	0.74506 (6)	0.0164 (3)
C2	0.90601 (10)	0.10631 (7)	0.69486 (6)	0.0154 (3)
C3	0.87363 (10)	0.08939 (8)	0.63990 (6)	0.0160 (3)
C4	0.93528 (11)	0.08057 (8)	0.59430 (7)	0.0197 (3)
H4	0.9117	0.0682	0.5587	0.024*
C5	1.03367 (11)	0.09057 (9)	0.60279 (7)	0.0225 (3)
H5	1.0762	0.0853	0.5726	0.027*
C6	1.06761 (11)	0.10838 (8)	0.65624 (7)	0.0219 (3)
H6	1.1330	0.1154	0.6616	0.026*
C7	1.00495 (11)	0.11593 (8)	0.70205 (6)	0.0185 (3)
H7	1.0290	0.1275	0.7377	0.022*
C8	0.84674 (10)	0.13210 (8)	0.84728 (6)	0.0177 (3)
C9	0.81731 (12)	0.19689 (8)	0.86650 (7)	0.0228 (3)
H9	0.8230	0.2364	0.8435	0.027*
C10	0.77882 (13)	0.20220 (9)	0.92121 (7)	0.0275 (4)
H10	0.7580	0.2455	0.9347	0.033*
C11	0.77150 (12)	0.14327 (9)	0.95554 (7)	0.0268 (4)
H11	0.7456	0.1471	0.9919	0.032*
C12	0.80273 (12)	0.07860 (9)	0.93585 (7)	0.0250 (4)
H12	0.7982	0.0393	0.9591	0.030*
C13	0.84102 (11)	0.07248 (8)	0.88115 (6)	0.0205 (3)
H13	0.8623	0.0293	0.8677	0.025*
C14	0.57410 (10)	0.87376 (8)	0.75055 (6)	0.0162 (3)
C15	0.64161 (10)	0.88144 (7)	0.80095 (6)	0.0155 (3)
C16	0.60961 (11)	0.90072 (8)	0.85538 (6)	0.0172 (3)
C17	0.67109 (11)	0.90830 (8)	0.90112 (7)	0.0207 (3)
H17	0.6479	0.9229	0.9363	0.025*
C18	0.76860 (11)	0.89371 (8)	0.89372 (7)	0.0224 (3)
H18	0.8107	0.8976	0.9242	0.027*
C19	0.80236 (11)	0.87336 (8)	0.84074 (7)	0.0216 (3)
H19	0.8672	0.8632	0.8360	0.026*
C20	0.73989 (11)	0.86791 (8)	0.79425 (6)	0.0185 (3)
H20	0.7637	0.8552	0.7587	0.022*
C21	0.58138 (10)	0.85411 (8)	0.64894 (6)	0.0179 (3)
C22	0.57809 (12)	0.91356 (9)	0.61514 (7)	0.0234 (3)
H22	0.6018	0.9561	0.6285	0.028*
C23	0.53869 (13)	0.90861 (9)	0.56075 (7)	0.0286 (4)
H23	0.5357	0.9482	0.5377	0.034*
C24	0.50406 (12)	0.84523 (10)	0.54099 (7)	0.0291 (4)
H24	0.4774	0.8423	0.5048	0.035*
C25	0.50903 (12)	0.78612 (10)	0.57510 (7)	0.0279 (4)
H25	0.4859	0.7435	0.5616	0.033*
C26	0.54851 (11)	0.79006 (9)	0.62969 (7)	0.0217 (3)
H26	0.5525	0.7504	0.6526	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0242 (2)	0.0232 (2)	0.0388 (2)	−0.00243 (16)	−0.00111 (17)	0.01232 (17)
Cl2	0.01487 (18)	0.0293 (2)	0.0349 (2)	0.00031 (15)	0.00139 (16)	0.00667 (17)
Cl3	0.01958 (18)	0.01759 (19)	0.02010 (18)	−0.00493 (14)	0.00219 (14)	0.00236 (14)
Cl4	0.02165 (18)	0.01817 (19)	0.02101 (18)	0.00552 (14)	−0.00079 (14)	0.00014 (15)
Cl5	0.01495 (19)	0.0518 (3)	0.0342 (2)	0.00156 (18)	−0.00068 (16)	0.0062 (2)
Cl6	0.0309 (2)	0.0225 (2)	0.0439 (3)	−0.00089 (17)	0.00383 (19)	0.00955 (18)
Cl7	0.02040 (18)	0.0202 (2)	0.02237 (19)	−0.00621 (14)	0.00056 (14)	−0.00114 (15)
Cl8	0.02351 (19)	0.0182 (2)	0.02227 (19)	0.00817 (15)	−0.00286 (15)	−0.00061 (15)
O1	0.0150 (5)	0.0206 (6)	0.0185 (5)	−0.0010 (4)	−0.0005 (4)	0.0029 (4)
O2	0.0367 (7)	0.0380 (7)	0.0229 (6)	−0.0004 (6)	−0.0056 (5)	−0.0083 (5)
O3	0.0147 (5)	0.0241 (6)	0.0161 (5)	−0.0026 (4)	−0.0003 (4)	0.0025 (4)
O4	0.0155 (5)	0.0216 (6)	0.0187 (5)	0.0018 (4)	0.0003 (4)	0.0010 (4)
O5	0.0399 (7)	0.0362 (7)	0.0198 (6)	−0.0005 (6)	0.0026 (5)	−0.0020 (5)
O6	0.0155 (5)	0.0209 (6)	0.0175 (5)	0.0027 (4)	0.0010 (4)	0.0004 (4)
P1	0.01636 (19)	0.0193 (2)	0.01725 (19)	−0.00067 (15)	−0.00209 (15)	0.00073 (16)
P2	0.0168 (2)	0.0228 (2)	0.0190 (2)	0.00033 (16)	0.00096 (15)	0.00126 (16)
C1	0.0150 (7)	0.0144 (8)	0.0197 (7)	−0.0012 (6)	−0.0011 (6)	0.0032 (6)
C2	0.0163 (7)	0.0122 (7)	0.0178 (7)	0.0011 (6)	0.0016 (6)	0.0047 (6)
C3	0.0138 (7)	0.0141 (8)	0.0201 (7)	0.0012 (6)	−0.0011 (6)	0.0028 (6)
C4	0.0214 (8)	0.0197 (8)	0.0181 (7)	0.0027 (6)	−0.0005 (6)	0.0020 (6)
C5	0.0188 (8)	0.0267 (9)	0.0220 (8)	0.0046 (7)	0.0056 (6)	0.0046 (7)
C6	0.0130 (7)	0.0274 (9)	0.0254 (8)	0.0008 (6)	0.0011 (6)	0.0079 (7)
C7	0.0183 (8)	0.0191 (8)	0.0182 (7)	−0.0007 (6)	−0.0020 (6)	0.0048 (6)
C8	0.0142 (7)	0.0229 (8)	0.0159 (7)	−0.0044 (6)	−0.0022 (6)	0.0014 (6)
C9	0.0292 (9)	0.0193 (8)	0.0198 (8)	−0.0061 (7)	−0.0029 (7)	0.0026 (6)
C10	0.0341 (10)	0.0255 (9)	0.0228 (8)	−0.0017 (7)	0.0002 (7)	−0.0054 (7)
C11	0.0286 (9)	0.0361 (10)	0.0156 (7)	−0.0082 (7)	0.0002 (6)	−0.0010 (7)
C12	0.0277 (9)	0.0280 (9)	0.0192 (8)	−0.0084 (7)	−0.0034 (7)	0.0074 (7)
C13	0.0215 (8)	0.0186 (8)	0.0215 (8)	−0.0019 (6)	−0.0043 (6)	0.0019 (6)
C14	0.0143 (7)	0.0121 (7)	0.0220 (7)	0.0009 (6)	0.0009 (6)	0.0011 (6)
C15	0.0156 (7)	0.0101 (7)	0.0206 (7)	−0.0014 (6)	−0.0020 (6)	0.0019 (6)
C16	0.0140 (7)	0.0141 (8)	0.0234 (8)	−0.0014 (6)	0.0006 (6)	0.0017 (6)
C17	0.0207 (8)	0.0213 (8)	0.0200 (8)	−0.0028 (6)	−0.0003 (6)	0.0003 (6)
C18	0.0200 (8)	0.0225 (9)	0.0248 (8)	−0.0046 (6)	−0.0061 (6)	0.0045 (7)
C19	0.0139 (7)	0.0214 (8)	0.0294 (9)	−0.0011 (6)	−0.0008 (6)	0.0061 (7)
C20	0.0180 (7)	0.0158 (8)	0.0216 (7)	−0.0003 (6)	0.0017 (6)	0.0028 (6)
C21	0.0129 (7)	0.0227 (8)	0.0183 (7)	0.0036 (6)	0.0022 (6)	0.0009 (6)
C22	0.0245 (8)	0.0205 (8)	0.0251 (8)	0.0015 (7)	0.0048 (7)	0.0033 (7)
C23	0.0331 (10)	0.0305 (10)	0.0223 (8)	0.0095 (8)	0.0044 (7)	0.0088 (7)
C24	0.0294 (9)	0.0402 (11)	0.0178 (8)	0.0118 (8)	−0.0022 (7)	−0.0006 (7)
C25	0.0302 (9)	0.0277 (10)	0.0257 (9)	0.0043 (7)	−0.0003 (7)	−0.0066 (7)
C26	0.0258 (8)	0.0183 (8)	0.0211 (8)	0.0055 (6)	0.0020 (6)	0.0012 (6)

Geometric parameters (Å, º)

Cl1—P1	1.9897 (6)	C9—C10	1.397 (2)
Cl2—P1	1.9935 (6)	C9—H9	0.9300
Cl3—C1	1.8063 (15)	C10—C11	1.387 (2)
Cl4—C1	1.8257 (15)	C10—H10	0.9300
Cl5—P2	1.9860 (6)	C11—C12	1.387 (2)
Cl6—P2	1.9917 (6)	C11—H11	0.9300
Cl7—C14	1.8277 (15)	C12—C13	1.397 (2)
Cl8—C14	1.8033 (15)	C12—H12	0.9300
O1—C3	1.4156 (17)	C13—H13	0.9300
O1—P1	1.572 (1)	C14—C15	1.520 (2)
O2—P1	1.453 (1)	C15—C20	1.403 (2)
O3—C1	1.383 (2)	C15—C16	1.404 (2)
O3—C8	1.422 (2)	C16—C17	1.382 (2)
O4—C16	1.4132 (18)	C17—C18	1.398 (2)
O4—P2	1.5786 (11)	C17—H17	0.9300
O5—P2	1.4523 (12)	C18—C19	1.386 (2)
O6—C14	1.3810 (18)	C18—H18	0.9300
O6—C21	1.4182 (17)	C19—C20	1.401 (2)
C1—C2	1.520 (2)	C19—H19	0.9300
C2—C7	1.401 (2)	C20—H20	0.9300
C2—C3	1.406 (2)	C21—C26	1.380 (2)
C3—C4	1.384 (2)	C21—C22	1.385 (2)
C4—C5	1.399 (2)	C22—C23	1.394 (2)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.385 (2)	C23—C24	1.381 (3)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.394 (2)	C24—C25	1.384 (3)
C6—H6	0.9300	C24—H24	0.9300
C7—H7	0.9300	C25—C26	1.398 (2)
C8—C9	1.378 (2)	C25—H25	0.9300
C8—C13	1.390 (2)	C26—H26	0.9300
C3—O1—P1	125.87 (9)	C12—C11—H11	119.9
C1—O3—C8	120.08 (11)	C10—C11—H11	119.9
C16—O4—P2	124.25 (9)	C11—C12—C13	120.07 (15)
C14—O6—C21	119.60 (11)	C11—C12—H12	120.0
O2—P1—O1	117.96 (7)	C13—C12—H12	120.0
O2—P1—Cl1	112.84 (6)	C8—C13—C12	118.74 (15)
O1—P1—Cl1	105.65 (5)	C8—C13—H13	120.6
O2—P1—Cl2	113.36 (6)	C12—C13—H13	120.6
O1—P1—Cl2	100.11 (4)	O6—C14—C15	108.81 (12)
Cl1—P1—Cl2	105.48 (3)	O6—C14—Cl8	110.96 (10)
O5—P2—O4	118.45 (7)	C15—C14—Cl8	110.78 (10)
O5—P2—Cl5	114.25 (6)	O6—C14—Cl7	110.30 (10)
O4—P2—Cl5	99.89 (4)	C15—C14—Cl7	109.32 (10)
O5—P2—Cl6	112.27 (6)	Cl8—C14—Cl7	106.65 (7)
O4—P2—Cl6	104.91 (5)	C20—C15—C16	117.43 (13)
Cl5—P2—Cl6	105.57 (3)	C20—C15—C14	119.96 (13)
O3—C1—C2	108.28 (12)	C16—C15—C14	122.60 (13)
O3—C1—Cl3	110.76 (10)	C17—C16—C15	122.63 (14)
C2—C1—Cl3	110.94 (10)	C17—C16—O4	120.41 (13)
O3—C1—Cl4	110.66 (10)	C15—C16—O4	116.95 (13)
C2—C1—Cl4	109.64 (10)	C16—C17—C18	119.01 (15)
Cl3—C1—Cl4	106.57 (8)	C16—C17—H17	120.5
C7—C2—C3	117.18 (13)	C18—C17—H17	120.5
C7—C2—C1	120.43 (13)	C19—C18—C17	119.83 (15)
C3—C2—C1	122.40 (13)	C19—C18—H18	120.1
C4—C3—C2	122.70 (14)	C17—C18—H18	120.1
C4—C3—O1	120.38 (13)	C18—C19—C20	120.68 (15)
C2—C3—O1	116.90 (12)	C18—C19—H19	119.7
C3—C4—C5	118.78 (14)	C20—C19—H19	119.7
C3—C4—H4	120.6	C19—C20—C15	120.38 (14)
C5—C4—H4	120.6	C19—C20—H20	119.8
C6—C5—C4	119.86 (14)	C15—C20—H20	119.8
C6—C5—H5	120.1	C26—C21—C22	121.67 (14)
C4—C5—H5	120.1	C26—C21—O6	119.67 (13)
C5—C6—C7	120.81 (14)	C22—C21—O6	118.43 (14)
C5—C6—H6	119.6	C21—C22—C23	118.91 (16)
C7—C6—H6	119.6	C21—C22—H22	120.5
C6—C7—C2	120.65 (14)	C23—C22—H22	120.5
C6—C7—H7	119.7	C24—C23—C22	120.32 (16)
C2—C7—H7	119.7	C24—C23—H23	119.8
C9—C8—C13	121.89 (14)	C22—C23—H23	119.8
C9—C8—O3	119.44 (13)	C23—C24—C25	119.98 (16)
C13—C8—O3	118.43 (14)	C23—C24—H24	120.0
C8—C9—C10	118.75 (15)	C25—C24—H24	120.0
C8—C9—H9	120.6	C24—C25—C26	120.49 (17)
C10—C9—H9	120.6	C24—C25—H25	119.8
C11—C10—C9	120.34 (16)	C26—C25—H25	119.8
C11—C10—H10	119.8	C21—C26—C25	118.61 (15)
C9—C10—H10	119.8	C21—C26—H26	120.7
C12—C11—C10	120.20 (15)	C25—C26—H26	120.7