(1-Oxo-2,6,7-trioxa-1-phosphabicyclo-[2.2.2]octan-4-yl)methyl 4-methyl-benzene-sulfonate.

In the title compound, C(12)H(15)O(7)PS, the P atom has a distorted tetra-hedral environment. The P-O-C-C torsion angles deviate significantly from zero [average = 12.0 (3)°], indicating that the bicyclic OP(OCH(2))(3)C cage is strained. In the crystal, weak C-H⋯O inter-actions consolidate the packing.

Related literature

For related structures, see: Miu et al. (1991 ▶); Sheng & He (2006 ▶); Guo & Zang (2007 ▶). For applications of caged bicyclic phosphates and p-toluene­sulfonates, see: Li et al. (2000 ▶); Yachi et al. (1989 ▶); Spungin et al. (1992 ▶).

Experimental

Crystal data

C12H15O7PS

M = 334.27

Monoclinic,

a = 5.8884 (17) Å

b = 19.440 (5) Å

c = 12.469 (4) Å

β = 100.614 (4)°

V = 1402.8 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.929, T max = 0.956

17318 measured reflections

3353 independent reflections

2808 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.03

3353 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku/MSC, 2005 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016674/cv5286sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016674/cv5286Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016674/cv5286Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H15O7PS	F(000) = 696
Mr = 334.27	Dx = 1.583 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.8884 (17) Å	Cell parameters from 4690 reflections
b = 19.440 (5) Å	θ = 1.0–27.9°
c = 12.469 (4) Å	µ = 0.38 mm−1
β = 100.614 (4)°	T = 113 K
V = 1402.8 (7) Å3	Prism, colorless
Z = 4	0.20 × 0.18 × 0.12 mm

Rigaku Saturn CCD area-detector diffractometer	3353 independent reflections
Radiation source: rotating anode	2808 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.042
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.0°
ω and φ scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −25→25
Tmin = 0.929, Tmax = 0.956	l = −16→16
17318 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.056P)2 + 0.0836P] where P = (Fo2 + 2Fc2)/3
3353 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.99063 (6)	0.451050 (18)	0.67038 (3)	0.01842 (11)
P1	0.39289 (8)	0.28254 (2)	0.29030 (3)	0.02821 (13)
O1	1.22894 (17)	0.45267 (5)	0.66257 (9)	0.0236 (2)
O2	0.84692 (19)	0.50895 (5)	0.63399 (9)	0.0278 (3)
O3	0.89302 (16)	0.38603 (5)	0.60079 (8)	0.0214 (2)
O4	0.20805 (18)	0.29396 (5)	0.36462 (8)	0.0237 (3)
O5	0.50318 (19)	0.35557 (6)	0.28262 (8)	0.0312 (3)
O6	0.5883 (2)	0.23944 (6)	0.36336 (10)	0.0380 (3)
O7	0.3039 (2)	0.25143 (8)	0.18528 (10)	0.0495 (4)
C1	0.9609 (2)	0.43084 (7)	0.80401 (11)	0.0181 (3)
C2	0.7696 (3)	0.45395 (8)	0.84399 (13)	0.0244 (3)
H2	0.6535	0.4805	0.7994	0.029*
C3	0.7513 (3)	0.43764 (8)	0.95002 (13)	0.0263 (3)
H3	0.6201	0.4530	0.9776	0.032*
C4	0.9193 (3)	0.39949 (8)	1.01712 (12)	0.0237 (3)
C5	1.1086 (3)	0.37578 (8)	0.97464 (13)	0.0261 (3)
H5	1.2237	0.3488	1.0191	0.031*
C6	1.1302 (3)	0.39112 (8)	0.86861 (12)	0.0229 (3)
H6	1.2591	0.3748	0.8401	0.028*
C7	0.8998 (3)	0.38445 (10)	1.13373 (13)	0.0340 (4)
H7A	0.7525	0.4022	1.1480	0.051*
H7B	1.0276	0.4067	1.1830	0.051*
H7C	0.9068	0.3346	1.1460	0.051*
C8	0.6458 (2)	0.37224 (9)	0.58979 (12)	0.0258 (4)
H8A	0.5611	0.4157	0.5953	0.031*
H8B	0.6176	0.3411	0.6488	0.031*
C9	0.5622 (2)	0.33904 (7)	0.47941 (11)	0.0170 (3)
C10	0.2981 (2)	0.33360 (8)	0.46400 (11)	0.0186 (3)
H10A	0.2546	0.3106	0.5281	0.022*
H10B	0.2294	0.3802	0.4580	0.022*
C11	0.6235 (3)	0.38303 (8)	0.38722 (12)	0.0224 (3)
H11A	0.5763	0.4313	0.3957	0.027*
H11B	0.7925	0.3821	0.3898	0.027*
C12	0.6632 (3)	0.26691 (8)	0.47338 (13)	0.0255 (3)
H12A	0.8340	0.2690	0.4908	0.031*
H12B	0.6096	0.2364	0.5273	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.0172 (2)	0.0208 (2)	0.01733 (19)	0.00029 (14)	0.00335 (14)	0.00003 (13)
P1	0.0281 (2)	0.0345 (3)	0.0219 (2)	0.00056 (18)	0.00434 (18)	−0.01078 (18)
O1	0.0179 (6)	0.0302 (6)	0.0238 (6)	−0.0038 (4)	0.0065 (4)	0.0001 (4)
O2	0.0312 (6)	0.0268 (6)	0.0249 (6)	0.0084 (5)	0.0036 (5)	0.0044 (5)
O3	0.0144 (5)	0.0287 (6)	0.0210 (5)	−0.0011 (4)	0.0032 (4)	−0.0062 (4)
O4	0.0219 (6)	0.0286 (6)	0.0199 (5)	−0.0056 (4)	0.0022 (4)	−0.0036 (4)
O5	0.0316 (6)	0.0469 (8)	0.0159 (5)	−0.0085 (5)	0.0063 (5)	0.0038 (5)
O6	0.0359 (7)	0.0306 (7)	0.0440 (7)	0.0096 (5)	−0.0019 (6)	−0.0168 (6)
O7	0.0439 (8)	0.0701 (10)	0.0329 (7)	−0.0012 (7)	0.0026 (6)	−0.0301 (7)
C1	0.0176 (7)	0.0202 (7)	0.0164 (7)	−0.0015 (6)	0.0029 (6)	−0.0019 (6)
C2	0.0186 (8)	0.0310 (9)	0.0234 (8)	0.0028 (6)	0.0032 (6)	−0.0026 (6)
C3	0.0214 (8)	0.0332 (9)	0.0267 (8)	−0.0017 (6)	0.0105 (7)	−0.0058 (7)
C4	0.0277 (8)	0.0230 (8)	0.0212 (8)	−0.0085 (6)	0.0064 (6)	−0.0037 (6)
C5	0.0294 (8)	0.0260 (8)	0.0225 (8)	0.0035 (7)	0.0040 (6)	0.0037 (6)
C6	0.0207 (7)	0.0259 (8)	0.0227 (8)	0.0041 (6)	0.0053 (6)	−0.0003 (6)
C7	0.0434 (11)	0.0379 (10)	0.0231 (8)	−0.0095 (8)	0.0128 (8)	−0.0014 (7)
C8	0.0160 (7)	0.0417 (10)	0.0204 (8)	−0.0065 (6)	0.0051 (6)	−0.0080 (7)
C9	0.0167 (7)	0.0192 (7)	0.0158 (7)	−0.0011 (5)	0.0044 (5)	0.0004 (5)
C10	0.0179 (7)	0.0240 (7)	0.0143 (7)	−0.0017 (6)	0.0036 (5)	−0.0009 (6)
C11	0.0227 (8)	0.0244 (8)	0.0212 (7)	−0.0049 (6)	0.0072 (6)	0.0018 (6)
C12	0.0226 (8)	0.0227 (8)	0.0297 (8)	0.0029 (6)	0.0006 (7)	0.0013 (6)

S1—O1	1.4248 (11)	C4—C7	1.508 (2)
S1—O2	1.4309 (11)	C5—C6	1.384 (2)
S1—O3	1.5803 (11)	C5—H5	0.9500
S1—C1	1.7518 (15)	C6—H6	0.9500
P1—O7	1.4499 (13)	C7—H7A	0.9800
P1—O4	1.5698 (11)	C7—H7B	0.9800
P1—O5	1.5714 (13)	C7—H7C	0.9800
P1—O6	1.5717 (13)	C8—C9	1.5177 (19)
O3—C8	1.4617 (17)	C8—H8A	0.9900
O4—C10	1.4724 (16)	C8—H8B	0.9900
O5—C11	1.4654 (18)	C9—C11	1.528 (2)
O6—C12	1.4623 (19)	C9—C12	1.530 (2)
C1—C2	1.387 (2)	C9—C10	1.5352 (19)
C1—C6	1.394 (2)	C10—H10A	0.9900
C2—C3	1.383 (2)	C10—H10B	0.9900
C2—H2	0.9500	C11—H11A	0.9900
C3—C4	1.387 (2)	C11—H11B	0.9900
C3—H3	0.9500	C12—H12A	0.9900
C4—C5	1.397 (2)	C12—H12B	0.9900
O1—S1—O2	119.56 (7)	C4—C7—H7B	109.5
O1—S1—O3	104.08 (6)	H7A—C7—H7B	109.5
O2—S1—O3	108.73 (7)	C4—C7—H7C	109.5
O1—S1—C1	110.02 (7)	H7A—C7—H7C	109.5
O2—S1—C1	108.73 (7)	H7B—C7—H7C	109.5
O3—S1—C1	104.64 (7)	O3—C8—C9	108.30 (11)
O7—P1—O4	114.69 (7)	O3—C8—H8A	110.0
O7—P1—O5	113.99 (8)	C9—C8—H8A	110.0
O4—P1—O5	104.33 (6)	O3—C8—H8B	110.0
O7—P1—O6	113.91 (8)	C9—C8—H8B	110.0
O4—P1—O6	104.27 (7)	H8A—C8—H8B	108.4
O5—P1—O6	104.49 (7)	C8—C9—C11	111.23 (12)
C8—O3—S1	116.97 (9)	C8—C9—C12	111.73 (12)
C10—O4—P1	112.92 (8)	C11—C9—C12	109.15 (12)
C11—O5—P1	114.35 (9)	C8—C9—C10	107.13 (11)
C12—O6—P1	114.27 (9)	C11—C9—C10	108.58 (12)
C2—C1—C6	120.88 (14)	C12—C9—C10	108.94 (12)
C2—C1—S1	119.94 (11)	O4—C10—C9	109.93 (11)
C6—C1—S1	119.18 (11)	O4—C10—H10A	109.7
C3—C2—C1	118.73 (14)	C9—C10—H10A	109.7
C3—C2—H2	120.6	O4—C10—H10B	109.7
C1—C2—H2	120.6	C9—C10—H10B	109.7
C2—C3—C4	121.78 (15)	H10A—C10—H10B	108.2
C2—C3—H3	119.1	O5—C11—C9	108.85 (12)
C4—C3—H3	119.1	O5—C11—H11A	109.9
C3—C4—C5	118.54 (14)	C9—C11—H11A	109.9
C3—C4—C7	120.85 (15)	O5—C11—H11B	109.9
C5—C4—C7	120.60 (15)	C9—C11—H11B	109.9
C6—C5—C4	120.75 (15)	H11A—C11—H11B	108.3
C6—C5—H5	119.6	O6—C12—C9	109.14 (12)
C4—C5—H5	119.6	O6—C12—H12A	109.9
C5—C6—C1	119.30 (14)	C9—C12—H12A	109.9
C5—C6—H6	120.4	O6—C12—H12B	109.9
C1—C6—H6	120.4	C9—C12—H12B	109.9
C4—C7—H7A	109.5	H12A—C12—H12B	108.3
O1—S1—O3—C8	−177.65 (10)	C2—C3—C4—C7	177.82 (15)
O2—S1—O3—C8	−49.18 (12)	C3—C4—C5—C6	1.2 (2)
C1—S1—O3—C8	66.86 (11)	C7—C4—C5—C6	−178.19 (15)
O7—P1—O4—C10	−172.57 (10)	C4—C5—C6—C1	0.1 (2)
O5—P1—O4—C10	−47.17 (10)	C2—C1—C6—C5	−1.2 (2)
O6—P1—O4—C10	62.18 (11)	S1—C1—C6—C5	179.22 (12)
O7—P1—O5—C11	−171.46 (10)	S1—O3—C8—C9	148.31 (10)
O4—P1—O5—C11	62.71 (11)	O3—C8—C9—C11	−54.43 (17)
O6—P1—O5—C11	−46.49 (11)	O3—C8—C9—C12	67.82 (16)
O7—P1—O6—C12	−174.29 (11)	O3—C8—C9—C10	−172.94 (12)
O4—P1—O6—C12	−48.55 (12)	P1—O4—C10—C9	−12.41 (14)
O5—P1—O6—C12	60.69 (12)	C8—C9—C10—O4	−172.94 (12)
O1—S1—C1—C2	152.36 (12)	C11—C9—C10—O4	66.84 (15)
O2—S1—C1—C2	19.67 (15)	C12—C9—C10—O4	−51.92 (15)
O3—S1—C1—C2	−96.37 (13)	P1—O5—C11—C9	−12.39 (15)
O1—S1—C1—C6	−28.07 (14)	C8—C9—C11—O5	−169.66 (12)
O2—S1—C1—C6	−160.76 (12)	C12—C9—C11—O5	66.61 (15)
O3—S1—C1—C6	83.21 (13)	C10—C9—C11—O5	−52.01 (15)
C6—C1—C2—C3	0.9 (2)	P1—O6—C12—C9	−11.31 (16)
S1—C1—C2—C3	−179.56 (12)	C8—C9—C12—O6	−176.46 (12)
C1—C2—C3—C4	0.6 (2)	C11—C9—C12—O6	−53.03 (16)
C2—C3—C4—C5	−1.6 (2)	C10—C9—C12—O6	65.37 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O5i	0.98	2.59	3.288 (2)	128
C8—H8A···O1ii	0.99	2.38	3.180 (2)	138
C10—H10A···O7iii	0.99	2.27	3.211 (2)	158
C10—H10B···O2iv	0.99	2.44	3.348 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O5i	0.98	2.59	3.288 (2)	128
C8—H8A⋯O1ii	0.99	2.38	3.180 (2)	138
C10—H10A⋯O7iii	0.99	2.27	3.211 (2)	158
C10—H10B⋯O2iv	0.99	2.44	3.348 (2)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .