(1S,3R,4R)-1,3,4,6-Tetra-O-acetyl-2-O-methyl­sulfonyl-α-D-mannopyran­oside

In the title compound, C₁₅H₂₂O₁₂S, the pyran­ose ring adopts a chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.091
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       5.83 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.46
           From the CIF: _reflns_number_total               4249
           Count of symmetry unique reflns         2455
           Completeness (_total/calc)            173.08%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1794
           Fraction of Friedel pairs measured     0.731
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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.

1,3,4,6-Tetra-O-acetyl-2-O-methylsulfonyl-α-D-mannopyranoside

Crystal data

C15H22O12S	F(000) = 896
Mr = 426.39	Dx = 1.358 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3654 reflections
a = 8.947 (2) Å	θ = 2.5–21.8°
b = 10.373 (3) Å	µ = 0.21 mm^−1
c = 22.477 (6) Å	T = 294 K
V = 2086.2 (9) Å^3	Block, colourless
Z = 4	0.28 × 0.24 × 0.18 mm

Data collection

Bruker SMART 1000 CCD diffractometer	4249 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 0 pixels mm^-1	θmax = 26.5°, θmin = 2.2°
ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.943, Tmax = 0.963	l = −28→15
11993 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0468P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.002
4249 reflections	Δρmax = 0.16 e Å^−3
257 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1794 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (8)

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
S1	0.84935 (8)	0.45716 (6)	0.91768 (3)	0.04702 (17)
O1	0.71709 (17)	0.78722 (16)	0.80713 (7)	0.0435 (4)
O2	0.72107 (19)	0.90122 (15)	0.89705 (7)	0.0461 (4)
O3	0.4734 (2)	0.9203 (2)	0.88474 (10)	0.0781 (6)
O4	0.83988 (18)	0.57287 (13)	0.87186 (6)	0.0435 (4)
O5	0.9438 (2)	0.4919 (2)	0.96576 (8)	0.0751 (6)
O6	0.8811 (2)	0.34776 (16)	0.88176 (8)	0.0629 (5)
O7	1.1372 (2)	0.77966 (17)	0.97279 (7)	0.0587 (5)
O8	1.12276 (17)	0.68656 (15)	0.88241 (6)	0.0433 (4)
O9	1.11484 (18)	0.84634 (15)	0.78029 (7)	0.0469 (4)
O10	1.2171 (2)	0.6673 (2)	0.74032 (10)	0.0768 (6)
O11	0.8404 (2)	0.74352 (15)	0.69022 (7)	0.0515 (4)
O12	0.7144 (3)	0.8078 (2)	0.60997 (10)	0.0968 (8)
C1	0.8522 (3)	0.7059 (2)	0.89314 (10)	0.0400 (5)
H1	0.8536	0.7083	0.9367	0.048*
C2	0.9939 (2)	0.7642 (2)	0.86810 (10)	0.0377 (5)
H2	1.0074	0.8504	0.8851	0.045*
C3	0.9861 (3)	0.7755 (2)	0.80070 (10)	0.0394 (6)
H3	0.9832	0.6898	0.7824	0.047*
C4	0.8465 (3)	0.8531 (2)	0.78379 (10)	0.0427 (6)
H4	0.8530	0.9387	0.8020	0.051*
C5	0.7156 (3)	0.7763 (2)	0.86929 (10)	0.0425 (6)
H5	0.6248	0.7311	0.8819	0.051*
C6	0.5908 (3)	0.9683 (3)	0.89826 (11)	0.0519 (7)
C7	0.6169 (4)	1.1047 (3)	0.91711 (14)	0.0741 (9)
H7A	0.5231	1.1495	0.9189	0.111*
H7B	0.6812	1.1465	0.8889	0.111*
H7C	0.6631	1.1058	0.9556	0.111*
C8	0.6659 (3)	0.4459 (3)	0.94438 (12)	0.0641 (8)
H8A	0.6390	0.5251	0.9637	0.096*
H8B	0.6592	0.3761	0.9723	0.096*
H8C	0.5991	0.4304	0.9117	0.096*
C9	1.1848 (3)	0.7042 (2)	0.93672 (11)	0.0440 (6)
C10	1.3173 (3)	0.6181 (3)	0.94429 (12)	0.0627 (8)
H10A	1.2866	0.5298	0.9406	0.094*
H10B	1.3603	0.6318	0.9829	0.094*
H10C	1.3901	0.6375	0.9142	0.094*
C11	1.2258 (3)	0.7795 (3)	0.75201 (11)	0.0541 (7)
C12	1.3528 (3)	0.8679 (3)	0.73854 (12)	0.0726 (9)
H12A	1.4123	0.8319	0.7071	0.109*
H12B	1.4132	0.8785	0.7735	0.109*
H12C	1.3145	0.9502	0.7263	0.109*
C13	0.8222 (3)	0.8685 (2)	0.71792 (10)	0.0496 (6)
H13A	0.7225	0.9014	0.7103	0.060*
H13B	0.8941	0.9290	0.7017	0.060*
C14	0.7875 (3)	0.7289 (3)	0.63557 (12)	0.0579 (7)
C15	0.8368 (4)	0.6022 (3)	0.61067 (13)	0.0820 (10)
H15A	0.9335	0.6117	0.5928	0.123*
H15B	0.7664	0.5740	0.5812	0.123*
H15C	0.8420	0.5397	0.6421	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0550 (4)	0.0399 (3)	0.0462 (3)	0.0053 (3)	0.0041 (3)	0.0033 (3)
O1	0.0389 (9)	0.0504 (10)	0.0413 (10)	−0.0004 (8)	−0.0013 (7)	0.0022 (8)
O2	0.0448 (10)	0.0419 (9)	0.0515 (10)	0.0031 (8)	0.0054 (8)	−0.0030 (8)
O3	0.0552 (14)	0.0768 (14)	0.1023 (17)	0.0152 (12)	−0.0032 (12)	−0.0166 (13)
O4	0.0561 (10)	0.0346 (8)	0.0397 (8)	−0.0032 (8)	0.0004 (8)	−0.0016 (7)
O5	0.0879 (16)	0.0732 (14)	0.0641 (12)	0.0016 (12)	−0.0275 (11)	0.0151 (11)
O6	0.0755 (13)	0.0420 (10)	0.0712 (13)	0.0164 (10)	0.0188 (10)	−0.0015 (9)
O7	0.0599 (12)	0.0652 (11)	0.0510 (10)	0.0070 (11)	−0.0079 (9)	−0.0219 (9)
O8	0.0406 (10)	0.0490 (9)	0.0404 (9)	0.0050 (8)	−0.0036 (7)	−0.0073 (7)
O9	0.0440 (10)	0.0474 (10)	0.0494 (10)	−0.0095 (8)	0.0075 (8)	0.0010 (8)
O10	0.0736 (15)	0.0680 (15)	0.0889 (16)	0.0110 (12)	0.0245 (11)	−0.0075 (12)
O11	0.0661 (12)	0.0511 (10)	0.0375 (9)	0.0058 (9)	−0.0068 (9)	0.0006 (7)
O12	0.142 (2)	0.0695 (14)	0.0786 (15)	−0.0034 (15)	−0.0599 (15)	0.0128 (12)
C1	0.0452 (14)	0.0371 (12)	0.0376 (12)	0.0018 (12)	0.0016 (11)	−0.0032 (10)
C2	0.0384 (13)	0.0365 (13)	0.0382 (13)	0.0028 (11)	−0.0008 (10)	−0.0025 (11)
C3	0.0395 (13)	0.0396 (13)	0.0390 (13)	−0.0037 (11)	0.0009 (10)	0.0002 (11)
C4	0.0513 (15)	0.0387 (12)	0.0382 (13)	−0.0075 (13)	0.0023 (12)	0.0012 (10)
C5	0.0422 (14)	0.0411 (14)	0.0441 (15)	−0.0010 (12)	0.0046 (11)	−0.0027 (12)
C6	0.0501 (17)	0.0533 (16)	0.0522 (16)	0.0103 (15)	0.0131 (12)	0.0058 (13)
C7	0.088 (2)	0.0459 (16)	0.089 (2)	0.0109 (16)	0.0267 (19)	0.0017 (16)
C8	0.073 (2)	0.0531 (16)	0.0656 (17)	−0.0032 (16)	0.0282 (15)	−0.0049 (14)
C9	0.0383 (14)	0.0514 (15)	0.0422 (14)	−0.0044 (12)	−0.0024 (11)	−0.0051 (12)
C10	0.0518 (18)	0.0699 (19)	0.0664 (18)	0.0080 (15)	−0.0095 (14)	−0.0046 (15)
C11	0.0449 (16)	0.073 (2)	0.0450 (16)	−0.0003 (16)	0.0042 (12)	0.0044 (15)
C12	0.0455 (17)	0.110 (3)	0.0622 (17)	−0.0141 (18)	0.0084 (15)	0.0046 (17)
C13	0.0601 (17)	0.0441 (14)	0.0448 (14)	0.0042 (13)	−0.0017 (12)	0.0035 (12)
C14	0.0709 (19)	0.0574 (18)	0.0453 (17)	−0.0200 (16)	−0.0099 (14)	0.0048 (14)
C15	0.118 (3)	0.073 (2)	0.0545 (17)	−0.014 (2)	−0.0002 (19)	−0.0129 (16)

Geometric parameters (Å, º)

S1—O5	1.418 (2)	C3—H3	0.9800
S1—O6	1.4213 (18)	C4—C13	1.505 (3)
S1—O4	1.5838 (16)	C4—H4	0.9800
S1—C8	1.751 (3)	C5—H5	0.9800
O1—C5	1.402 (3)	C6—C7	1.496 (4)
O1—C4	1.443 (3)	C7—H7A	0.9600
O2—C6	1.358 (3)	C7—H7B	0.9600
O2—C5	1.439 (3)	C7—H7C	0.9600
O3—C6	1.201 (3)	C8—H8A	0.9600
O4—C1	1.465 (3)	C8—H8B	0.9600
O7—C9	1.205 (3)	C8—H8C	0.9600
O8—C9	1.353 (3)	C9—C10	1.494 (3)
O8—C2	1.443 (3)	C10—H10A	0.9600
O9—C11	1.367 (3)	C10—H10B	0.9600
O9—C3	1.441 (3)	C10—H10C	0.9600
O10—C11	1.196 (3)	C11—C12	1.491 (4)
O11—C14	1.325 (3)	C12—H12A	0.9600
O11—C13	1.447 (3)	C12—H12B	0.9600
O12—C14	1.196 (3)	C12—H12C	0.9600
C1—C2	1.513 (3)	C13—H13A	0.9700
C1—C5	1.521 (3)	C13—H13B	0.9700
C1—H1	0.9800	C14—C15	1.494 (4)
C2—C3	1.521 (3)	C15—H15A	0.9600
C2—H2	0.9800	C15—H15B	0.9600
C3—C4	1.533 (3)	C15—H15C	0.9600
O5—S1—O6	121.09 (12)	C6—C7—H7A	109.5
O5—S1—O4	109.58 (11)	C6—C7—H7B	109.5
O6—S1—O4	104.27 (9)	H7A—C7—H7B	109.5
O5—S1—C8	108.32 (13)	C6—C7—H7C	109.5
O6—S1—C8	109.17 (13)	H7A—C7—H7C	109.5
O4—S1—C8	102.90 (12)	H7B—C7—H7C	109.5
C5—O1—C4	114.08 (17)	S1—C8—H8A	109.5
C6—O2—C5	116.2 (2)	S1—C8—H8B	109.5
C1—O4—S1	119.85 (13)	H8A—C8—H8B	109.5
C9—O8—C2	116.96 (17)	S1—C8—H8C	109.5
C11—O9—C3	118.0 (2)	H8A—C8—H8C	109.5
C14—O11—C13	117.5 (2)	H8B—C8—H8C	109.5
O4—C1—C2	108.53 (18)	O7—C9—O8	123.4 (2)
O4—C1—C5	106.08 (19)	O7—C9—C10	126.3 (2)
C2—C1—C5	110.50 (18)	O8—C9—C10	110.3 (2)
O4—C1—H1	110.5	C9—C10—H10A	109.5
C2—C1—H1	110.5	C9—C10—H10B	109.5
C5—C1—H1	110.5	H10A—C10—H10B	109.5
O8—C2—C1	111.35 (18)	C9—C10—H10C	109.5
O8—C2—C3	107.55 (18)	H10A—C10—H10C	109.5
C1—C2—C3	111.29 (19)	H10B—C10—H10C	109.5
O8—C2—H2	108.9	O10—C11—O9	123.3 (3)
C1—C2—H2	108.9	O10—C11—C12	127.1 (3)
C3—C2—H2	108.9	O9—C11—C12	109.6 (3)
O9—C3—C2	108.66 (19)	C11—C12—H12A	109.5
O9—C3—C4	107.73 (18)	C11—C12—H12B	109.5
C2—C3—C4	108.94 (18)	H12A—C12—H12B	109.5
O9—C3—H3	110.5	C11—C12—H12C	109.5
C2—C3—H3	110.5	H12A—C12—H12C	109.5
C4—C3—H3	110.5	H12B—C12—H12C	109.5
O1—C4—C13	106.97 (19)	O11—C13—C4	108.16 (19)
O1—C4—C3	108.37 (17)	O11—C13—H13A	110.1
C13—C4—C3	114.67 (19)	C4—C13—H13A	110.1
O1—C4—H4	108.9	O11—C13—H13B	110.1
C13—C4—H4	108.9	C4—C13—H13B	110.1
C3—C4—H4	108.9	H13A—C13—H13B	108.4
O1—C5—O2	111.07 (19)	O12—C14—O11	124.3 (3)
O1—C5—C1	112.49 (18)	O12—C14—C15	125.7 (3)
O2—C5—C1	104.61 (18)	O11—C14—C15	110.0 (3)
O1—C5—H5	109.5	C14—C15—H15A	109.5
O2—C5—H5	109.5	C14—C15—H15B	109.5
C1—C5—H5	109.5	H15A—C15—H15B	109.5
O3—C6—O2	122.2 (2)	C14—C15—H15C	109.5
O3—C6—C7	126.9 (3)	H15A—C15—H15C	109.5
O2—C6—C7	110.9 (3)	H15B—C15—H15C	109.5
O5—S1—O4—C1	−31.2 (2)	O9—C3—C4—C13	64.0 (2)
O6—S1—O4—C1	−162.15 (18)	C2—C3—C4—C13	−178.3 (2)
C8—S1—O4—C1	83.91 (19)	C4—O1—C5—O2	58.7 (2)
S1—O4—C1—C2	114.54 (17)	C4—O1—C5—C1	−58.1 (2)
S1—O4—C1—C5	−126.71 (16)	C6—O2—C5—O1	78.2 (2)
C9—O8—C2—C1	−82.9 (2)	C6—O2—C5—C1	−160.23 (19)
C9—O8—C2—C3	154.95 (19)	O4—C1—C5—O1	−66.4 (2)
O4—C1—C2—O8	−54.8 (2)	C2—C1—C5—O1	51.0 (2)
C5—C1—C2—O8	−170.76 (18)	O4—C1—C5—O2	172.89 (16)
O4—C1—C2—C3	65.2 (2)	C2—C1—C5—O2	−69.7 (2)
C5—C1—C2—C3	−50.8 (2)	C5—O2—C6—O3	10.1 (3)
C11—O9—C3—C2	106.7 (2)	C5—O2—C6—C7	−168.9 (2)
C11—O9—C3—C4	−135.4 (2)	C2—O8—C9—O7	0.4 (3)
O8—C2—C3—O9	−65.1 (2)	C2—O8—C9—C10	−179.4 (2)
C1—C2—C3—O9	172.66 (17)	C3—O9—C11—O10	4.6 (4)
O8—C2—C3—C4	177.75 (17)	C3—O9—C11—C12	−175.9 (2)
C1—C2—C3—C4	55.5 (2)	C14—O11—C13—C4	163.3 (2)
C5—O1—C4—C13	−174.13 (19)	O1—C4—C13—O11	−72.8 (2)
C5—O1—C4—C3	61.7 (2)	C3—C4—C13—O11	47.3 (3)
O9—C3—C4—O1	−176.55 (17)	C13—O11—C14—O12	−7.1 (4)
C2—C3—C4—O1	−58.8 (2)	C13—O11—C14—C15	171.1 (2)