Methyl 2,3,6-tri-O-benzoyl-α-D-xylo-hexo­pyran­osid-4-ulose

In the title compound, C₂₈H₂₄O₉, the pyran­ose ring adopts a distorted chair conformation due to the presence of a ketone function at position 4 of the ring. The torsion angle of the exocyclic hydroxy­methyl group is shown to be gauche–trans with respect to atoms O-1 and C-4, respectively.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.065
• wR factor = 0.035
• Data-to-parameter ratio = 10.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           29.97
         From the CIF: _reflns_number_total               4024
         Count of symmetry unique reflns         3998
         Completeness (_total/calc)            100.65%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured        26
         Fraction of Friedel pairs measured     0.007
         Are heavy atom types Z>Si present           no
          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.

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: TEXSAN (Molecular Structure Corporation, 1992-1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C28H24O9	Dx = 1.368 Mg m^−3
Mr = 504.49	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 8.848 (5) Å	θ = 10.3–11.7°
b = 12.843 (2) Å	µ = 0.10 mm^−1
c = 21.551 (4) Å	T = 293 K
V = 2449 (1) Å^3	Orthorhombic prism, colourless
Z = 4	0.35 × 0.34 × 0.31 mm
F(000) = 1056.00

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0
Radiation source: X-ray tube	θmax = 30.0°, θmin = 2.3°
Graphite monochromator	h = 0→12
ω scans	k = 0→18
4024 measured reflections	l = 0→30
4024 independent reflections	2 standard reflections every 120 reflections
3389 reflections with I > 0.1σ(I)	intensity decay: 0.3%

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.035	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo) + 0.00002|Fo|^2]
S = 1.93	(Δ/σ)max = 0.005
3389 reflections	Δρmax = 0.20 e Å^−3
334 parameters	Δρmin = −0.23 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.4496 (1)	0.49685 (9)	0.13212 (6)	0.0568 (4)
O2	−0.1343 (1)	0.48864 (9)	0.10785 (6)	0.0488 (4)
O3	−0.0656 (1)	0.64558 (8)	0.20019 (6)	0.0494 (3)
O4	−0.2838 (2)	0.7755 (1)	0.23007 (7)	0.0724 (4)
O5	−0.4521 (1)	0.66981 (9)	0.09769 (5)	0.0512 (4)
O6	−0.6755 (1)	0.81359 (9)	0.12662 (6)	0.0524 (4)
O7	−0.0745 (2)	0.5317 (1)	0.01026 (6)	0.0747 (5)
O8	−0.0165 (2)	0.4860 (1)	0.23842 (6)	0.0629 (4)
O9	−0.7115 (1)	0.9794 (1)	0.15394 (8)	0.0768 (5)
C1	−0.3830 (2)	0.5706 (1)	0.09368 (8)	0.0495 (5)
C2	−0.2191 (2)	0.5840 (1)	0.11454 (8)	0.0461 (5)
C3	−0.2152 (2)	0.6151 (1)	0.18183 (8)	0.0432 (5)
C4	−0.3165 (2)	0.7085 (1)	0.19342 (8)	0.0469 (5)
C5	−0.4674 (2)	0.7104 (1)	0.15867 (8)	0.0460 (5)
C6	−0.5250 (2)	0.8193 (1)	0.15356 (9)	0.0525 (6)
C7	−0.5982 (2)	0.4666 (2)	0.1119 (1)	0.0896 (8)
C8	−0.0623 (2)	0.4733 (1)	0.05351 (9)	0.0491 (5)
C9	0.0304 (2)	0.3776 (1)	0.05481 (8)	0.0449 (5)
C10	0.0839 (2)	0.3387 (2)	−0.00112 (9)	0.0616 (6)
C11	0.1687 (3)	0.2488 (2)	−0.0021 (1)	0.0760 (7)
C12	0.2011 (2)	0.1980 (2)	0.0521 (1)	0.0739 (7)
C13	0.1504 (2)	0.2368 (2)	0.1078 (1)	0.0646 (7)
C14	0.0637 (2)	0.3269 (1)	0.10923 (9)	0.0523 (6)
C15	0.0170 (2)	0.5752 (1)	0.23206 (8)	0.0470 (5)
C16	0.1548 (2)	0.6254 (1)	0.25858 (8)	0.0428 (5)
C17	0.2705 (2)	0.5611 (1)	0.27991 (9)	0.0549 (6)
C18	0.3945 (2)	0.6048 (2)	0.3089 (1)	0.0638 (6)
C19	0.4023 (2)	0.7108 (2)	0.3175 (1)	0.0648 (7)
C20	0.2890 (2)	0.7746 (2)	0.2964 (1)	0.0632 (6)
C21	0.1641 (2)	0.7318 (1)	0.26594 (9)	0.0506 (5)
C22	−0.7559 (2)	0.9020 (1)	0.12914 (9)	0.0502 (6)
C23	−0.9052 (2)	0.8916 (1)	0.09783 (8)	0.0430 (5)
C24	−0.9439 (2)	0.8075 (1)	0.06223 (9)	0.0489 (5)
C25	−1.0818 (2)	0.8050 (2)	0.03198 (9)	0.0571 (6)
C26	−1.1815 (2)	0.8864 (2)	0.03872 (9)	0.0629 (7)
C27	−1.1441 (2)	0.9696 (2)	0.0744 (1)	0.0727 (7)
C28	−1.0052 (2)	0.9734 (2)	0.1043 (1)	0.0616 (6)
H1	−0.3855	0.5469	0.0519	0.059*
H2	−0.1728	0.6370	0.0904	0.055*
H3	−0.2478	0.5583	0.2067	0.052*
H4	−0.5390	0.6697	0.1808	0.055*
H5	−0.5296	0.8504	0.1935	0.063*
H6	−0.4603	0.8591	0.1276	0.063*
H7	−0.6393	0.4175	0.1403	0.108*
H8	−0.6616	0.5262	0.1102	0.108*
H9	−0.5919	0.4360	0.0718	0.108*
H10	0.0619	0.3741	−0.0388	0.074*
H11	0.2048	0.2220	−0.0405	0.091*
H12	0.2588	0.1356	0.0512	0.089*
H13	0.1747	0.2020	0.1454	0.077*
H14	0.0276	0.3533	0.1476	0.063*
H15	0.2642	0.4878	0.2746	0.066*
H16	0.4747	0.5615	0.3228	0.077*
H17	0.4868	0.7401	0.3383	0.078*
H18	0.2955	0.8477	0.3024	0.076*
H19	0.0864	0.7757	0.2505	0.061*
H20	−0.8758	0.7507	0.0583	0.059*
H21	−1.1076	0.7471	0.0066	0.069*
H22	−1.2767	0.8844	0.0184	0.076*
H23	−1.2134	1.0256	0.0790	0.087*
H24	−0.9791	1.0319	0.1291	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0372 (7)	0.0523 (8)	0.0808 (9)	−0.0048 (7)	−0.0150 (7)	0.0058 (7)
O2	0.0424 (7)	0.0472 (7)	0.0569 (7)	0.0071 (7)	0.0055 (6)	0.0060 (6)
O3	0.0311 (6)	0.0454 (7)	0.0718 (8)	−0.0012 (6)	−0.0156 (6)	0.0065 (6)
O4	0.0555 (8)	0.0697 (9)	0.092 (1)	0.0123 (8)	−0.0243 (8)	−0.0279 (8)
O5	0.0472 (7)	0.0524 (7)	0.0540 (7)	0.0111 (7)	−0.0134 (7)	0.0015 (6)
O6	0.0361 (7)	0.0478 (7)	0.0734 (8)	0.0065 (7)	−0.0108 (7)	−0.0019 (7)
O7	0.091 (1)	0.0698 (9)	0.0630 (9)	0.015 (1)	0.0143 (9)	0.0161 (8)
O8	0.0602 (8)	0.0451 (7)	0.0834 (9)	−0.0046 (7)	−0.0259 (8)	0.0088 (7)
O9	0.0432 (8)	0.0537 (8)	0.134 (1)	0.0059 (8)	−0.0235 (9)	−0.0240 (9)
C1	0.046 (1)	0.047 (1)	0.056 (1)	0.008 (1)	−0.013 (1)	−0.003 (1)
C2	0.038 (1)	0.042 (1)	0.058 (1)	0.0028 (9)	0.000 (1)	0.0045 (9)
C3	0.0313 (9)	0.044 (1)	0.054 (1)	−0.0022 (9)	−0.0075 (9)	0.0041 (9)
C4	0.038 (1)	0.047 (1)	0.055 (1)	0.002 (1)	−0.005 (1)	0.000 (1)
C5	0.0337 (9)	0.050 (1)	0.054 (1)	0.0028 (9)	−0.0066 (9)	0.0018 (9)
C6	0.0323 (9)	0.051 (1)	0.075 (1)	0.003 (1)	−0.007 (1)	−0.002 (1)
C7	0.049 (1)	0.082 (2)	0.138 (2)	−0.015 (1)	−0.032 (1)	−0.008 (2)
C8	0.042 (1)	0.052 (1)	0.053 (1)	−0.008 (1)	0.001 (1)	−0.001 (1)
C9	0.0302 (9)	0.045 (1)	0.060 (1)	−0.0084 (9)	0.0037 (9)	−0.002 (1)
C10	0.047 (1)	0.071 (1)	0.067 (1)	−0.003 (1)	0.007 (1)	−0.002 (1)
C11	0.062 (1)	0.080 (1)	0.085 (1)	0.011 (1)	0.021 (1)	−0.012 (1)
C12	0.050 (1)	0.068 (1)	0.104 (2)	0.016 (1)	0.013 (1)	−0.006 (1)
C13	0.050 (1)	0.061 (1)	0.083 (1)	0.004 (1)	−0.001 (1)	0.006 (1)
C14	0.039 (1)	0.052 (1)	0.065 (1)	−0.003 (1)	0.004 (1)	−0.004 (1)
C15	0.041 (1)	0.048 (1)	0.052 (1)	0.007 (1)	−0.008 (1)	0.001 (1)
C16	0.0324 (9)	0.048 (1)	0.048 (1)	0.0013 (9)	−0.0030 (9)	−0.0012 (9)
C17	0.044 (1)	0.055 (1)	0.065 (1)	0.005 (1)	−0.010 (1)	0.007 (1)
C18	0.040 (1)	0.077 (1)	0.074 (1)	0.003 (1)	−0.012 (1)	0.011 (1)
C19	0.043 (1)	0.088 (2)	0.063 (1)	−0.015 (1)	−0.011 (1)	−0.002 (1)
C20	0.056 (1)	0.061 (1)	0.073 (1)	−0.006 (1)	−0.005 (1)	−0.014 (1)
C21	0.038 (1)	0.053 (1)	0.062 (1)	0.004 (1)	−0.003 (1)	−0.005 (1)
C22	0.037 (1)	0.045 (1)	0.069 (1)	0.0050 (9)	0.000 (1)	−0.002 (1)
C23	0.0307 (9)	0.046 (1)	0.052 (1)	0.0027 (9)	0.0009 (9)	0.0010 (9)
C24	0.040 (1)	0.048 (1)	0.059 (1)	0.000 (1)	0.004 (1)	0.005 (1)
C25	0.056 (1)	0.064 (1)	0.051 (1)	−0.016 (1)	−0.001 (1)	0.006 (1)
C26	0.040 (1)	0.088 (2)	0.060 (1)	0.001 (1)	−0.003 (1)	0.003 (1)
C27	0.053 (1)	0.083 (2)	0.083 (1)	0.025 (1)	−0.011 (1)	−0.009 (1)
C28	0.047 (1)	0.064 (1)	0.074 (1)	0.011 (1)	−0.010 (1)	−0.012 (1)

Geometric parameters (Å, º)

O1—C1	1.390 (2)	C10—H10	0.95
O1—C7	1.439 (2)	C11—C12	1.369 (3)
O2—C2	1.444 (2)	C11—H11	0.95
O2—C8	1.348 (2)	C12—C13	1.376 (3)
O3—C3	1.436 (2)	C12—H12	0.95
O3—C15	1.350 (2)	C13—C14	1.388 (3)
O4—C4	1.204 (2)	C13—H13	0.95
O5—C1	1.415 (2)	C14—H14	0.95
O5—C5	1.421 (2)	C15—C16	1.493 (2)
O6—C6	1.455 (2)	C16—C17	1.393 (2)
O6—C22	1.340 (2)	C16—C21	1.378 (2)
O7—C8	1.202 (2)	C17—C18	1.381 (3)
O8—C15	1.191 (2)	C17—H15	0.95
O9—C22	1.195 (2)	C18—C19	1.376 (3)
C1—C2	1.528 (3)	C18—H16	0.95
C1—H1	0.95	C19—C20	1.372 (3)
C2—C3	1.504 (2)	C19—H17	0.95
C2—H2	0.95	C20—C21	1.398 (3)
C3—C4	1.519 (2)	C20—H18	0.95
C3—H3	0.95	C21—H19	0.95
C4—C5	1.531 (2)	C22—C23	1.490 (2)
C5—C6	1.492 (2)	C23—C24	1.368 (2)
C5—H4	0.95	C23—C28	1.380 (2)
C6—H5	0.95	C24—C25	1.384 (3)
C6—H6	0.95	C24—H20	0.95
C7—H7	0.95	C25—C26	1.376 (3)
C7—H8	0.95	C25—H21	0.95
C7—H9	0.95	C26—C27	1.358 (3)
C8—C9	1.478 (2)	C26—H22	0.95
C9—C10	1.388 (2)	C27—C28	1.388 (3)
C9—C14	1.373 (2)	C27—H23	0.95
C10—C11	1.378 (3)	C28—H24	0.95
C1—O1—C7	113.0 (2)	C10—C11—H11	120.0
C2—O2—C8	117.2 (1)	C12—C11—H11	120.0
C3—O3—C15	117.1 (1)	C11—C12—C13	120.2 (2)
C1—O5—C5	115.4 (1)	C11—C12—H12	119.9
C6—O6—C22	115.3 (1)	C13—C12—H12	119.9
O1—C1—O5	113.2 (1)	C12—C13—C14	120.1 (2)
O1—C1—C2	107.7 (1)	C12—C13—H13	119.9
O1—C1—H1	109.7	C14—C13—H13	119.9
O5—C1—C2	106.9 (1)	C9—C14—C13	119.7 (2)
O5—C1—H1	109.7	C9—C14—H14	120.2
C2—C1—H1	109.7	C13—C14—H14	120.2
O2—C2—C1	111.6 (1)	O3—C15—O8	124.6 (2)
O2—C2—C3	108.0 (1)	O3—C15—C16	110.3 (1)
O2—C2—H2	109.2	O8—C15—C16	125.0 (2)
C1—C2—C3	109.6 (1)	C15—C16—C17	118.1 (2)
C1—C2—H2	109.2	C15—C16—C21	121.4 (2)
C3—C2—H2	109.2	C17—C16—C21	120.3 (2)
O3—C3—C2	111.0 (1)	C16—C17—C18	119.5 (2)
O3—C3—C4	106.5 (1)	C16—C17—H15	120.2
O3—C3—H3	109.5	C18—C17—H15	120.2
C2—C3—C4	110.7 (1)	C17—C18—C19	120.2 (2)
C2—C3—H3	109.5	C17—C18—H16	119.9
C4—C3—H3	109.5	C19—C18—H16	119.9
O4—C4—C3	122.1 (2)	C18—C19—C20	120.6 (2)
O4—C4—C5	121.3 (2)	C18—C19—H17	119.7
C3—C4—C5	116.6 (2)	C20—C19—H17	119.7
O5—C5—C4	111.3 (1)	C19—C20—C21	119.9 (2)
O5—C5—C6	108.0 (1)	C19—C20—H18	120.0
O5—C5—H4	109.0	C21—C20—H18	120.0
C4—C5—C6	110.4 (1)	C16—C21—C20	119.4 (2)
C4—C5—H4	109.0	C16—C21—H19	120.3
C6—C5—H4	109.0	C20—C21—H19	120.3
O6—C6—C5	107.2 (1)	O6—C22—O9	123.2 (2)
O6—C6—H5	110.0	O6—C22—C23	112.1 (2)
O6—C6—H6	110.0	O9—C22—C23	124.6 (2)
C5—C6—H5	110.0	C22—C23—C24	123.1 (2)
C5—C6—H6	110.0	C22—C23—C28	117.1 (2)
H5—C6—H6	109.5	C24—C23—C28	119.8 (2)
O1—C7—H7	109.5	C23—C24—C25	120.2 (2)
O1—C7—H8	109.5	C23—C24—H20	119.9
O1—C7—H9	109.5	C25—C24—H20	119.9
H7—C7—H8	109.5	C24—C25—C26	119.8 (2)
H7—C7—H9	109.5	C24—C25—H21	120.1
H8—C7—H9	109.5	C26—C25—H21	120.1
O2—C8—O7	122.7 (2)	C25—C26—C27	120.1 (2)
O2—C8—C9	111.6 (2)	C25—C26—H22	120.0
O7—C8—C9	125.7 (2)	C27—C26—H22	120.0
C8—C9—C10	118.2 (2)	C26—C27—C28	120.4 (2)
C8—C9—C14	122.0 (2)	C26—C27—H23	119.8
C10—C9—C14	119.9 (2)	C28—C27—H23	119.8
C9—C10—C11	120.0 (2)	C23—C28—C27	119.6 (2)
C9—C10—H10	120.0	C23—C28—H24	120.2
C11—C10—H10	120.0	C27—C28—H24	120.2
C10—C11—C12	120.1 (2)
O1—C1—O5—C5	52.1 (2)	C2—O2—C8—C9	175.1 (1)
O1—C1—C2—O2	62.4 (2)	C2—C1—O1—C7	−171.9 (2)
O1—C1—C2—C3	−57.2 (2)	C2—C1—O5—C5	−66.3 (2)
O2—C2—C1—O5	−175.7 (1)	C2—C3—O3—C15	−101.3 (2)
O2—C2—C3—O3	68.1 (2)	C2—C3—C4—C5	39.5 (2)
O2—C2—C3—C4	−173.8 (1)	C3—O3—C15—C16	−168.5 (1)
O2—C8—C9—C10	165.9 (2)	C3—C2—O2—C8	−148.9 (1)
O2—C8—C9—C14	−13.9 (2)	C3—C4—C5—C6	−157.4 (2)
O3—C3—C2—C1	−170.1 (1)	C4—C3—O3—C15	138.1 (1)
O3—C3—C4—O4	−23.0 (2)	C5—C6—O6—C22	168.1 (2)
O3—C3—C4—C5	160.3 (1)	C6—O6—C22—C23	177.0 (1)
O3—C15—C16—C17	−164.9 (2)	C8—C9—C10—C11	−179.0 (2)
O3—C15—C16—C21	19.6 (2)	C8—C9—C14—C13	179.5 (2)
O4—C4—C3—C2	−143.8 (2)	C9—C10—C11—C12	−0.4 (3)
O4—C4—C5—O5	145.8 (2)	C9—C14—C13—C12	−0.8 (3)
O4—C4—C5—C6	25.9 (2)	C10—C9—C14—C13	−0.2 (3)
O5—C1—O1—C7	70.2 (2)	C10—C11—C12—C13	−0.6 (4)
O5—C1—C2—C3	64.8 (2)	C11—C10—C9—C14	0.8 (3)
O5—C5—C4—C3	−37.5 (2)	C11—C12—C13—C14	1.2 (3)
O5—C5—C6—O6	64.5 (2)	C15—C16—C17—C18	−175.2 (2)
O6—C6—C5—C4	−173.6 (1)	C15—C16—C21—C20	173.9 (2)
O6—C22—C23—C24	−10.0 (2)	C16—C17—C18—C19	1.1 (3)
O6—C22—C23—C28	172.0 (2)	C16—C21—C20—C19	1.3 (3)
O7—C8—O2—C2	−4.9 (3)	C17—C16—C21—C20	−1.6 (3)
O7—C8—C9—C10	−14.2 (3)	C17—C18—C19—C20	−1.5 (3)
O7—C8—C9—C14	166.1 (2)	C18—C17—C16—C21	0.4 (3)
O8—C15—O3—C3	11.0 (3)	C18—C19—C20—C21	0.2 (3)
O8—C15—C16—C17	15.7 (3)	C22—C23—C24—C25	−176.9 (2)
O8—C15—C16—C21	−159.9 (2)	C22—C23—C28—C27	177.8 (2)
O9—C22—O6—C6	−3.1 (3)	C23—C24—C25—C26	−1.2 (3)
O9—C22—C23—C24	170.2 (2)	C23—C28—C27—C26	−0.4 (3)
O9—C22—C23—C28	−7.8 (3)	C24—C23—C28—C27	−0.2 (3)
C1—O5—C5—C4	52.1 (2)	C24—C25—C26—C27	0.7 (3)
C1—O5—C5—C6	173.5 (1)	C25—C24—C23—C28	1.0 (3)
C1—C2—O2—C8	90.6 (2)	C25—C26—C27—C28	0.1 (3)
C1—C2—C3—C4	−52.1 (2)