2-Chloro-1,3-dioxa-2σ³λ³-phosphaphen­anthren-4-one

The mol­ecule of the title compound, C₁₁H₆ClO₃P, is essentially planar, except for the P and Cl atoms. Bond lengths at phospho­rus are P—O = 1.6141 (8) and 1.6143 (9), and P—Cl = 2.0958 (4) Å. The mol­ecules are linked to form double ribbons parallel to the b axis by one C—H...O and one C—H...Cl interaction.

Key indicators

• Single-crystal X-ray study
• T = 143 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.088
• Data-to-parameter ratio = 21.1

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry

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S1. Comment

The title compound, (I), was obtained as a synthetic intermediate en route to phosphorus-substituted calix[4]arenes (Kunze, 2002; Kunze et al., 2002).

The structure of (I) is shown in Fig. 1. Bond lengths and angles may be considered normal (Table 1). All non-H atoms, except P and Cl, are coplanar (r.m.s. deviation 0.031 Å); these atoms lie 0.451 (1) and 2.511 (1) Å, respectively, on the same side of the plane.

The molecular packing involves three contacts. Two `weak' hydrogen bonds, one C—H···O and one C—H···Cl (Table 2), link the molecules in double ribbons parallel to the y axis (Fig. 2). A further Cl···Cl contact of 3.6114 (6) Å (operator −x − 1, −y, −z), not shown in Fig. 2, links adjacent ribbons in the z direction.

The structure of an isomeric material was presented in the preceding paper (Jones et al., 2002).

S2. Experimental

The title compound was prepared by the reaction of 2-hydroxynaphthalene-1-carboxylic acid with phosphorus trichloride in toluene and recrystallized from dichloromethane/diethyl ether (2:1 v/v) (Kunze, 2002). The bulk material had a greenish hue, although individual crystals are essentially colourless.

S3. Refinement

H atoms were included using a riding model with fixed C—H bond lengths of 0.95 Å; U_iso(H) values were fixed at 1.2 times the U_eq value of the parent atom.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecule of the title compound in the crystal. Ellipsoids represent 30% probability levels. H-atom radii are arbitrary.
	Fig. 2. Packing diagram of the title compound, with the view direction approximately perpendicular to the xy plane. Secondary interactions are indicated by dashed bonds.

2-Chloro-1,3-dioxa-2σ³λ³-phosphaphenanthren-4-one

Crystal data

C11H6ClO3P	Z = 2
Mr = 252.58	F(000) = 256
Triclinic, P1	Dx = 1.661 Mg m^−3
a = 7.1026 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3633 (8) Å	Cell parameters from 6669 reflections
c = 10.1786 (10) Å	θ = 2–30°
α = 103.794 (3)°	µ = 0.52 mm^−1
β = 102.520 (3)°	T = 143 K
γ = 113.390 (3)°	Tablet, colourless
V = 504.96 (8) Å^3	0.40 × 0.36 × 0.14 mm

Data collection

Bruker SMART diffractometer	3053 independent reflections
Radiation source: fine-focus sealed tube	2780 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.192 pixels mm^-1	θmax = 30.5°, θmin = 2.2°
ω and ϕ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −11→11
Tmin = 0.812, Tmax = 0.930	l = −14→14
8958 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0587P)^2 + 0.0767P] where P = (Fo^2 + 2Fc^2)/3
3053 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.24 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.

Non-bonded contact:

3.6114 (0.0006) Cl - Cl_$3

Operators for generating equivalent atoms: $3 − x − 1, −y, −z

#==============================================

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.1478 (0.0009) x + 0.5239 (0.0013) y − 1.3333 (0.0015) z = 1.0532 (0.0007)

* 0.0426 (0.0007) O1 * −0.0511 (0.0007) O2 * 0.0720 (0.0007) O3 * −0.0360 (0.0008) C1 * −0.0001 (0.0008) C2 * 0.0242 (0.0008) C3 * −0.0011 (0.0008) C4 * −0.0033 (0.0008) C5 * 0.0177 (0.0009) C6 * 0.0136 (0.0009) C7 * −0.0184 (0.0009) C8 * −0.0297 (0.0008) C9 * −0.0174 (0.0008) C10 * −0.0128 (0.0008) C11 − 0.4510 (0.0006) P −2.5107 (0.0006) Cl

Rms deviation of fitted atoms = 0.0313

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
P	0.09194 (5)	0.36207 (4)	0.11449 (3)	0.02635 (9)
Cl	−0.23379 (4)	0.20244 (4)	0.09468 (3)	0.02911 (9)
O1	0.19258 (13)	0.23130 (11)	0.15694 (8)	0.02653 (16)
O2	0.17718 (13)	0.52211 (10)	0.27047 (8)	0.02512 (16)
O3	0.23857 (13)	0.62941 (10)	0.50341 (8)	0.02476 (16)
C1	0.22604 (14)	0.33182 (12)	0.40971 (10)	0.01767 (17)
C2	0.21614 (15)	0.20579 (14)	0.28765 (11)	0.02056 (18)
C3	0.23386 (16)	0.04449 (14)	0.28774 (12)	0.0246 (2)
H3	0.2278	−0.0373	0.2023	0.030*
C4	0.25985 (16)	0.00605 (13)	0.41144 (12)	0.0238 (2)
H4	0.2681	−0.1047	0.4109	0.029*
C5	0.30829 (16)	0.08902 (15)	0.66903 (12)	0.0246 (2)
H5	0.3165	−0.0222	0.6668	0.029*
C6	0.32908 (17)	0.20879 (16)	0.79624 (12)	0.0269 (2)
H6	0.3528	0.1816	0.8819	0.032*
C7	0.31490 (17)	0.37259 (16)	0.79827 (12)	0.0255 (2)
H7	0.3301	0.4559	0.8865	0.031*
C8	0.27946 (16)	0.41474 (13)	0.67545 (11)	0.02108 (18)
H8	0.2686	0.5254	0.6798	0.025*
C9	0.25900 (14)	0.29458 (12)	0.54234 (10)	0.01767 (17)
C10	0.27478 (14)	0.12923 (13)	0.54088 (11)	0.02017 (18)
C11	0.21432 (14)	0.50224 (13)	0.40524 (10)	0.01884 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P	0.03240 (15)	0.02898 (15)	0.01982 (14)	0.01540 (12)	0.00969 (11)	0.01030 (10)
Cl	0.02612 (14)	0.02920 (14)	0.02641 (14)	0.01334 (11)	0.00333 (10)	0.00577 (10)
O1	0.0305 (4)	0.0326 (4)	0.0200 (3)	0.0186 (3)	0.0102 (3)	0.0077 (3)
O2	0.0314 (4)	0.0216 (3)	0.0217 (3)	0.0118 (3)	0.0076 (3)	0.0096 (3)
O3	0.0334 (4)	0.0190 (3)	0.0250 (3)	0.0152 (3)	0.0108 (3)	0.0075 (3)
C1	0.0164 (4)	0.0159 (4)	0.0202 (4)	0.0079 (3)	0.0061 (3)	0.0054 (3)
C2	0.0187 (4)	0.0211 (4)	0.0199 (4)	0.0097 (3)	0.0060 (3)	0.0043 (3)
C3	0.0224 (4)	0.0205 (4)	0.0264 (5)	0.0117 (4)	0.0053 (4)	0.0011 (3)
C4	0.0202 (4)	0.0165 (4)	0.0319 (5)	0.0097 (3)	0.0058 (4)	0.0052 (4)
C5	0.0211 (4)	0.0236 (4)	0.0336 (5)	0.0118 (4)	0.0094 (4)	0.0159 (4)
C6	0.0250 (4)	0.0328 (5)	0.0290 (5)	0.0150 (4)	0.0102 (4)	0.0183 (4)
C7	0.0268 (5)	0.0291 (5)	0.0233 (5)	0.0143 (4)	0.0104 (4)	0.0107 (4)
C8	0.0225 (4)	0.0203 (4)	0.0222 (4)	0.0112 (3)	0.0087 (3)	0.0078 (3)
C9	0.0151 (3)	0.0163 (4)	0.0213 (4)	0.0075 (3)	0.0061 (3)	0.0064 (3)
C10	0.0156 (4)	0.0170 (4)	0.0279 (5)	0.0079 (3)	0.0067 (3)	0.0085 (3)
C11	0.0166 (4)	0.0180 (4)	0.0213 (4)	0.0076 (3)	0.0062 (3)	0.0075 (3)

Geometric parameters (Å, º)

P—O2	1.6141 (8)	C4—C10	1.4190 (14)
P—O1	1.6143 (9)	C4—H4	0.9500
P—Cl	2.0958 (4)	C5—C6	1.372 (2)
O1—C2	1.3823 (12)	C5—C10	1.4176 (14)
O2—C11	1.4020 (12)	C5—H5	0.9500
O3—C11	1.1968 (12)	C6—C7	1.409 (2)
C1—C2	1.3923 (13)	C6—H6	0.9500
C1—C9	1.4476 (13)	C7—C8	1.3765 (14)
C1—C11	1.4710 (13)	C7—H7	0.9500
C2—C3	1.4040 (14)	C8—C9	1.4199 (13)
C3—C4	1.365 (2)	C8—H8	0.9500
C3—H3	0.9500	C9—C10	1.4279 (13)
O2—P—O1	100.81 (4)	C10—C5—H5	119.6
O2—P—Cl	99.62 (3)	C5—C6—C7	119.23 (10)
O1—P—Cl	99.76 (3)	C5—C6—H6	120.4
C2—O1—P	122.78 (6)	C7—C6—H6	120.4
C11—O2—P	127.24 (7)	C8—C7—C6	121.53 (10)
C2—C1—C9	117.98 (9)	C8—C7—H7	119.2
C2—C1—C11	120.75 (9)	C6—C7—H7	119.2
C9—C1—C11	121.20 (8)	C7—C8—C9	120.67 (9)
O1—C2—C1	122.69 (9)	C7—C8—H8	119.7
O1—C2—C3	114.41 (9)	C9—C8—H8	119.7
C1—C2—C3	122.89 (9)	C8—C9—C10	117.64 (9)
C4—C3—C2	119.51 (9)	C8—C9—C1	123.70 (8)
C4—C3—H3	120.2	C10—C9—C1	118.65 (9)
C2—C3—H3	120.2	C5—C10—C4	119.86 (9)
C3—C4—C10	120.93 (9)	C5—C10—C9	120.12 (9)
C3—C4—H4	119.5	C4—C10—C9	120.01 (9)
C10—C4—H4	119.5	O3—C11—O2	115.51 (9)
C6—C5—C10	120.80 (9)	O3—C11—C1	128.06 (9)
C6—C5—H5	119.6	O2—C11—C1	116.39 (8)
O2—P—O1—C2	33.25 (9)	C2—C1—C9—C8	177.81 (8)
Cl—P—O1—C2	−68.60 (8)	C11—C1—C9—C8	0.83 (13)
O1—P—O2—C11	−30.88 (9)	C2—C1—C9—C10	−1.38 (13)
Cl—P—O2—C11	71.09 (8)	C11—C1—C9—C10	−178.37 (8)
P—O1—C2—C1	−21.95 (13)	C6—C5—C10—C4	178.23 (9)
P—O1—C2—C3	159.32 (7)	C6—C5—C10—C9	−0.92 (14)
C9—C1—C2—O1	−177.77 (8)	C3—C4—C10—C5	−178.12 (9)
C11—C1—C2—O1	−0.77 (14)	C3—C4—C10—C9	1.03 (14)
C9—C1—C2—C3	0.84 (14)	C8—C9—C10—C5	0.40 (13)
C11—C1—C2—C3	177.84 (8)	C1—C9—C10—C5	179.64 (8)
O1—C2—C3—C4	179.38 (9)	C8—C9—C10—C4	−178.75 (8)
C1—C2—C3—C4	0.7 (2)	C1—C9—C10—C4	0.49 (13)
C2—C3—C4—C10	−1.6 (2)	P—O2—C11—O3	−166.86 (7)
C10—C5—C6—C7	0.5 (2)	P—O2—C11—C1	15.11 (12)
C5—C6—C7—C8	0.4 (2)	C2—C1—C11—O3	−173.29 (9)
C6—C7—C8—C9	−0.9 (2)	C9—C1—C11—O3	3.6 (2)
C7—C8—C9—C10	0.48 (14)	C2—C1—C11—O2	4.45 (13)
C7—C8—C9—C1	−178.72 (9)	C9—C1—C11—O2	−178.65 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3^i	0.95	2.57	3.4512 (13)	155
C8—H8···Cl^ii	0.95	2.95	3.6622 (10)	133
C8—H8···O3	0.95	2.18	2.8402 (13)	126

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