4/6-O-(p-Tolyl­sulfon­yl)-myo-inositol

The title compound, C₁₃H₁₈O₈S, packs in hydrogen-bonded layers in the crystal structure; the aromatic ring subtends an angle of 80.09 (14)° to the plane describing the inositol chair.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.134
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.42 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.41 Ratio

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 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
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: Collect (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and maXus(Mackay et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Xtal3.7 (Hall et al., 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

4/6-O-(para-toluenesulfonyl)-myo-inositol

Crystal data

C13H18O8S	F(000) = 704
Mr = 334.33	Dx = 1.518 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5796 reflections
a = 21.3935 (4) Å	θ = 1.0–27.5°
b = 6.7060 (1) Å	µ = 0.26 mm^−1
c = 10.1986 (2) Å	T = 173 K
β = 90.938 (1)°	Plate, colourless
V = 1462.94 (5) Å^3	0.25 × 0.25 × 0.03 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2548 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Horizonally mounted graphite crystal monochromator	θmax = 27.1°, θmin = 3.2°
Detector resolution: 9 pixels mm^-1	h = −26→25
φ scans and ω scans with κ offsets	k = −8→0
5632 measured reflections	l = −12→12
3186 independent 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 1.7383P] where P = (Fo^2 + 2Fc^2)/3
3186 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

Experimental. ¹H NMR (500 MHz, MeOD₄, δ, p.p.m.: 2.54 (s, 3H, Me), 3.41 (t, J = 9.5 Hz, 1H, H-6), 3.45 (dd, J = 2.5 Hz, J = 9.8 Hz, 1H, H-1), 3.65 (dd, J = 2.5 Hz, J = 9.8 Hz, 1H, H-3), 3.75 (t, J = 9.5 Hz, 1H, H-5), 4.05 (m, 1H, H-2), 4.90 (t, J = 9.5 Hz, 1H, H-4), 7.48 (d, J = 8.0 Hz, 2H, H Aromatic), 7.97 (d, J = 8.0 Hz, 2H, H Aromatic). ¹³C NMR (125 MHz, MeOD₄, δ: 20.5 (Me), 70.2, 71.9, 73.0, 73.2, 73.4, 85.8, 128.2, 129.4, 135.7, 144.6. ESI-MS: [M+Na]⁺= 357.05, [2M+Na]⁺= 691.1. analysis, calculated for C₁₃H₁₈O₈S: C, 46.70; H, 5.43. Found: C, 46.52; H, 5.49.

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
O1	0.00913 (8)	0.1276 (3)	0.30257 (15)	0.0205 (4)
H1A	−0.0112	0.0969	0.3694	0.031*
O2	0.07130 (8)	−0.1321 (2)	0.48563 (15)	0.0189 (4)
H2A	0.0680	−0.2564	0.4778	0.028*
O3	0.20049 (8)	−0.2098 (2)	0.44637 (15)	0.0193 (4)
H3A	0.2151	−0.2675	0.3806	0.029*
O4	0.24699 (8)	0.1599 (2)	0.54351 (15)	0.0195 (4)
O5	0.16053 (8)	0.4582 (2)	0.58708 (14)	0.0188 (4)
H5A	0.1681	0.5727	0.5579	0.028*
O6	0.06185 (9)	0.4918 (2)	0.40360 (18)	0.0279 (4)
H6A	0.0361	0.4785	0.3411	0.042*
O7	0.24461 (9)	−0.0683 (3)	0.73193 (16)	0.0276 (4)
O8	0.32403 (9)	0.1964 (3)	0.71277 (18)	0.0337 (5)
S1	0.28572 (3)	0.04706 (9)	0.65187 (5)	0.02009 (18)
C1	0.07374 (11)	0.1461 (3)	0.3372 (2)	0.0163 (5)
H1	0.0959	0.1958	0.2580	0.020*
C2	0.10290 (11)	−0.0530 (3)	0.3748 (2)	0.0160 (5)
H2	0.0981	−0.1476	0.2995	0.019*
C3	0.17250 (11)	−0.0261 (3)	0.4069 (2)	0.0155 (5)
H3	0.1941	0.0255	0.3276	0.019*
C4	0.18056 (10)	0.1226 (3)	0.5182 (2)	0.0143 (5)
H4	0.1605	0.0703	0.5992	0.017*
C5	0.15248 (11)	0.3238 (3)	0.4813 (2)	0.0146 (5)
H5	0.1749	0.3773	0.4035	0.017*
C6	0.08319 (11)	0.3004 (3)	0.4452 (2)	0.0164 (5)
H6	0.0597	0.2585	0.5245	0.020*
C7	0.33386 (12)	−0.1120 (4)	0.5610 (2)	0.0222 (5)
C8	0.33476 (15)	−0.3118 (4)	0.5829 (3)	0.0415 (8)
H8	0.3082	−0.3697	0.6461	0.050*
C9	0.37508 (17)	−0.4300 (5)	0.5115 (4)	0.0507 (9)
H9	0.3761	−0.5694	0.5280	0.061*
C10	0.41344 (13)	−0.3531 (5)	0.4183 (3)	0.0334 (7)
C11	0.4099 (2)	−0.1526 (6)	0.3961 (4)	0.0628 (12)
H11	0.4355	−0.0952	0.3309	0.075*
C12	0.3702 (2)	−0.0304 (5)	0.4653 (4)	0.0615 (12)
H12	0.3682	0.1083	0.4469	0.074*
C13	0.45649 (15)	−0.4832 (6)	0.3397 (3)	0.0491 (9)
H13A	0.4981	−0.4225	0.3378	0.059*
H13B	0.4399	−0.4963	0.2500	0.059*
H13C	0.4594	−0.6154	0.3804	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0215 (9)	0.0213 (9)	0.0186 (8)	−0.0005 (7)	−0.0042 (6)	−0.0025 (7)
O2	0.0224 (9)	0.0118 (8)	0.0227 (8)	−0.0018 (7)	0.0061 (7)	−0.0005 (6)
O3	0.0259 (9)	0.0129 (8)	0.0191 (8)	0.0050 (7)	0.0038 (6)	−0.0009 (6)
O4	0.0177 (9)	0.0207 (9)	0.0200 (8)	−0.0028 (7)	−0.0012 (6)	0.0052 (7)
O5	0.0292 (10)	0.0131 (8)	0.0140 (8)	−0.0038 (7)	−0.0010 (6)	−0.0025 (6)
O6	0.0370 (11)	0.0119 (8)	0.0343 (10)	0.0042 (8)	−0.0194 (8)	−0.0011 (7)
O7	0.0308 (10)	0.0349 (11)	0.0174 (8)	0.0078 (8)	0.0071 (7)	0.0095 (7)
O8	0.0327 (11)	0.0367 (11)	0.0311 (10)	0.0000 (9)	−0.0105 (8)	−0.0103 (9)
S1	0.0213 (3)	0.0241 (3)	0.0149 (3)	0.0025 (2)	−0.0013 (2)	0.0009 (2)
C1	0.0193 (12)	0.0140 (11)	0.0156 (11)	−0.0014 (9)	−0.0011 (8)	−0.0012 (8)
C2	0.0225 (12)	0.0117 (11)	0.0137 (10)	−0.0010 (9)	0.0015 (9)	−0.0021 (8)
C3	0.0186 (12)	0.0131 (11)	0.0149 (10)	0.0012 (9)	0.0033 (8)	0.0001 (8)
C4	0.0165 (11)	0.0142 (11)	0.0120 (10)	−0.0020 (9)	0.0007 (8)	0.0013 (8)
C5	0.0224 (12)	0.0115 (11)	0.0098 (10)	−0.0016 (9)	0.0001 (8)	0.0002 (8)
C6	0.0237 (13)	0.0096 (10)	0.0160 (11)	0.0019 (9)	−0.0014 (9)	−0.0007 (8)
C7	0.0200 (13)	0.0272 (13)	0.0194 (12)	0.0026 (10)	0.0006 (9)	0.0015 (10)
C8	0.0401 (18)	0.0268 (15)	0.058 (2)	0.0045 (13)	0.0240 (15)	0.0088 (14)
C9	0.051 (2)	0.0252 (16)	0.077 (3)	0.0079 (15)	0.0297 (18)	0.0011 (16)
C10	0.0251 (15)	0.0425 (17)	0.0326 (15)	0.0069 (13)	−0.0009 (11)	−0.0105 (13)
C11	0.072 (3)	0.054 (2)	0.064 (2)	0.005 (2)	0.048 (2)	0.0041 (19)
C12	0.080 (3)	0.0323 (18)	0.074 (3)	0.0048 (18)	0.051 (2)	0.0095 (17)
C13	0.0321 (17)	0.066 (2)	0.0499 (19)	0.0138 (16)	0.0035 (14)	−0.0221 (17)

Geometric parameters (Å, º)

O1—C1	1.426 (3)	C3—H3	1.0000
O1—H1A	0.8400	C4—C5	1.522 (3)
O2—C2	1.429 (3)	C4—H4	1.0000
O2—H2A	0.8400	C5—C6	1.529 (3)
O3—C3	1.425 (3)	C5—H5	1.0000
O3—H3A	0.8400	C6—H6	1.0000
O4—C4	1.462 (3)	C7—C8	1.359 (4)
O4—S1	1.5653 (16)	C7—C12	1.372 (4)
O5—C5	1.415 (3)	C8—C9	1.386 (4)
O5—H5A	0.8400	C8—H8	0.9500
O6—C6	1.424 (3)	C9—C10	1.367 (4)
O6—H6A	0.8400	C9—H9	0.9500
O7—S1	1.4358 (18)	C10—C11	1.365 (5)
O8—S1	1.430 (2)	C10—C13	1.509 (4)
S1—C7	1.757 (3)	C11—C12	1.382 (5)
C1—C2	1.520 (3)	C11—H11	0.9500
C1—C6	1.523 (3)	C12—H12	0.9500
C1—H1	1.0000	C13—H13A	0.9800
C2—C3	1.530 (3)	C13—H13B	0.9800
C2—H2	1.0000	C13—H13C	0.9800
C3—C4	1.519 (3)
C1—O1—H1A	109.5	O5—C5—C4	109.47 (17)
C2—O2—H2A	109.5	O5—C5—C6	110.75 (18)
C3—O3—H3A	109.5	C4—C5—C6	110.23 (18)
C4—O4—S1	122.93 (13)	O5—C5—H5	108.8
C5—O5—H5A	109.5	C4—C5—H5	108.8
C6—O6—H6A	109.5	C6—C5—H5	108.8
O8—S1—O7	118.84 (12)	O6—C6—C1	111.04 (18)
O8—S1—O4	105.13 (11)	O6—C6—C5	106.50 (18)
O7—S1—O4	109.87 (10)	C1—C6—C5	111.12 (18)
O8—S1—C7	108.52 (12)	O6—C6—H6	109.4
O7—S1—C7	110.04 (12)	C1—C6—H6	109.4
O4—S1—C7	103.24 (10)	C5—C6—H6	109.4
O1—C1—C2	112.22 (18)	C8—C7—C12	120.2 (3)
O1—C1—C6	110.78 (18)	C8—C7—S1	121.3 (2)
C2—C1—C6	111.43 (18)	C12—C7—S1	118.5 (2)
O1—C1—H1	107.4	C7—C8—C9	119.0 (3)
C2—C1—H1	107.4	C7—C8—H8	120.5
C6—C1—H1	107.4	C9—C8—H8	120.5
O2—C2—C1	109.17 (18)	C10—C9—C8	122.3 (3)
O2—C2—C3	110.22 (17)	C10—C9—H9	118.8
C1—C2—C3	110.15 (18)	C8—C9—H9	118.8
O2—C2—H2	109.1	C11—C10—C9	117.0 (3)
C1—C2—H2	109.1	C11—C10—C13	121.0 (3)
C3—C2—H2	109.1	C9—C10—C13	122.0 (3)
O3—C3—C4	108.30 (17)	C10—C11—C12	122.1 (3)
O3—C3—C2	111.19 (18)	C10—C11—H11	118.9
C4—C3—C2	109.61 (18)	C12—C11—H11	118.9
O3—C3—H3	109.2	C7—C12—C11	119.2 (3)
C4—C3—H3	109.2	C7—C12—H12	120.4
C2—C3—H3	109.2	C11—C12—H12	120.4
O4—C4—C3	110.03 (18)	C10—C13—H13A	109.5
O4—C4—C5	105.70 (17)	C10—C13—H13B	109.5
C3—C4—C5	110.93 (17)	H13A—C13—H13B	109.5
O4—C4—H4	110.0	C10—C13—H13C	109.5
C3—C4—H4	110.0	H13A—C13—H13C	109.5
C5—C4—H4	110.0	H13B—C13—H13C	109.5
C4—O4—S1—O8	−138.13 (17)	O1—C1—C6—C5	−179.04 (17)
C4—O4—S1—O7	−9.2 (2)	C2—C1—C6—C5	55.3 (2)
C4—O4—S1—C7	108.19 (18)	O5—C5—C6—O6	62.6 (2)
O1—C1—C2—O2	−60.6 (2)	C4—C5—C6—O6	−176.14 (17)
C6—C1—C2—O2	64.3 (2)	O5—C5—C6—C1	−176.38 (17)
O1—C1—C2—C3	178.29 (17)	C4—C5—C6—C1	−55.1 (2)
C6—C1—C2—C3	−56.8 (2)	O8—S1—C7—C8	123.6 (3)
O2—C2—C3—O3	57.7 (2)	O7—S1—C7—C8	−8.0 (3)
C1—C2—C3—O3	178.21 (17)	O4—S1—C7—C8	−125.2 (3)
O2—C2—C3—C4	−62.0 (2)	O8—S1—C7—C12	−57.3 (3)
C1—C2—C3—C4	58.5 (2)	O7—S1—C7—C12	171.1 (3)
S1—O4—C4—C3	−95.59 (19)	O4—S1—C7—C12	53.9 (3)
S1—O4—C4—C5	144.58 (15)	C12—C7—C8—C9	3.1 (5)
O3—C3—C4—O4	62.5 (2)	S1—C7—C8—C9	−177.9 (3)
C2—C3—C4—O4	−176.05 (16)	C7—C8—C9—C10	−1.0 (6)
O3—C3—C4—C5	179.08 (17)	C8—C9—C10—C11	−1.0 (6)
C2—C3—C4—C5	−59.4 (2)	C8—C9—C10—C13	−179.1 (3)
O4—C4—C5—O5	−61.0 (2)	C9—C10—C11—C12	0.9 (6)
C3—C4—C5—O5	179.75 (18)	C13—C10—C11—C12	179.1 (4)
O4—C4—C5—C6	176.92 (16)	C8—C7—C12—C11	−3.1 (6)
C3—C4—C5—C6	57.7 (2)	S1—C7—C12—C11	177.8 (3)
O1—C1—C6—O6	−60.7 (2)	C10—C11—C12—C7	1.1 (7)
C2—C1—C6—O6	173.63 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2^i	0.84	1.99	2.784 (2)	158
O2—H2A···O6^ii	0.84	1.85	2.664 (2)	161
O3—H3A···O7^iii	0.84	1.98	2.821 (2)	173
O5—H5A···O3^iv	0.84	1.98	2.790 (2)	161
O6—H6A···O1^v	0.84	2.01	2.730 (2)	143
O6—H6A···O1	0.84	2.45	2.874 (2)	112

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