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In the crystal structure of the title compound, C13H19ClO8, extensive inter­molecular hydrogen bonding leads to a three-dimensional network, but the Cl substituent is not involved in these inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024706/sg2041sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024706/sg2041Isup2.hkl
Contains datablock I

CCDC reference: 618324

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.033
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



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 28.50 From the CIF: _reflns_number_total 3896 Count of symmetry unique reflns 2235 Completeness (_total/calc) 174.32% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1661 Fraction of Friedel pairs measured 0.743 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS.

2,3,5,-Tri-O-acetyl-1-(2-chloroethyl)-β-D-ribofuranose top
Crystal data top
C13H19ClO8F(000) = 712
Mr = 338.74Dx = 1.465 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2300 reflections
a = 7.3407 (5) Åθ = 3–29°
b = 13.5532 (14) ŵ = 0.29 mm1
c = 15.4384 (9) ÅT = 173 K
V = 1536.0 (2) Å3Block, colourless
Z = 40.28 × 0.26 × 0.22 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
2801 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.075
φ and ω scansθmax = 28.5°, θmin = 3.0°
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
h = 99
Tmin = 0.93, Tmax = 0.94k = 1818
46023 measured reflectionsl = 2020
3896 independent reflections
Refinement top
Refinement on FHydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029 w = [1-(Fo-Fc)2/36σ2(F)]2/[2.46To(x)- 0.945T1(x) + 1.98T2(x)-0.132T3(x) + 0.288T4(x)],
where Ti are the Chebychev polynomials and x = Fc/Fmax (Prince, 1982; Watkin, 1994)
wR(F2) = 0.033(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.20 e Å3
2801 reflectionsΔρmin = 0.18 e Å3
200 parametersAbsolute structure: Flack (1983), with 1663 Friedel-pairs
0 restraintsAbsolute structure parameter: 0.01 (6)
Primary atom site location: structure-invariant direct methods
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.17803 (9)0.77456 (5)0.70851 (3)0.0462
C10.0403 (2)0.66542 (13)0.97976 (10)0.0218
C20.1299 (2)0.56750 (12)0.99970 (10)0.0214
C30.0022 (2)0.49744 (12)0.95621 (10)0.0190
C40.1855 (2)0.54351 (12)0.97671 (10)0.0203
C50.3353 (2)0.52188 (13)0.91281 (11)0.0254
C60.0506 (3)0.79044 (13)0.87353 (12)0.0250
C70.1898 (3)0.83112 (14)0.81275 (11)0.0284
C80.3415 (3)0.63447 (13)0.79545 (12)0.0271
C90.2838 (3)0.64797 (17)0.70370 (13)0.0392
C100.1312 (2)0.33920 (13)0.95749 (10)0.0221
C110.1098 (3)0.23765 (13)0.99245 (13)0.0278
C120.2618 (3)0.50901 (14)1.13072 (11)0.0263
C130.2348 (3)0.50509 (18)1.22664 (12)0.0394
O10.09964 (18)0.69256 (9)0.89716 (8)0.0253
O20.15018 (16)0.64701 (9)0.98146 (8)0.0236
O30.28216 (16)0.54702 (9)0.82603 (8)0.0249
O40.4309 (2)0.69079 (12)0.83609 (10)0.0433
O50.00059 (17)0.39937 (8)0.99004 (8)0.0217
O60.24413 (18)0.36722 (10)0.90784 (9)0.0292
O70.12075 (17)0.55489 (10)1.09188 (8)0.0254
O80.3907 (2)0.47818 (12)1.09234 (9)0.0400
H110.06960.71701.01950.0220*
H210.25460.55860.98260.0223*
H310.02800.49060.89690.0203*
H410.23320.51531.02830.0211*
H510.43990.56100.92760.0273*
H520.36690.45310.91540.0273*
H610.04140.83010.92410.0262*
H620.06510.78950.84480.0262*
H710.16730.90070.80670.0298*
H720.30790.82110.83780.0298*
H910.16370.62130.69610.0483*
H920.28290.71700.68980.0483*
H930.36730.61420.66610.0483*
H1110.01980.20290.95920.0346*
H1120.07180.24091.05190.0346*
H1130.22410.20350.98870.0346*
H1310.11880.53441.23990.0420*
H1320.33030.54231.25360.0420*
H1330.23730.43821.24700.0420*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0582 (3)0.0568 (3)0.0236 (2)0.0061 (3)0.0007 (2)0.0029 (2)
C10.0245 (8)0.0220 (8)0.0190 (7)0.0015 (7)0.0001 (6)0.0002 (6)
C20.0208 (8)0.0247 (8)0.0187 (7)0.0017 (7)0.0017 (6)0.0027 (6)
C30.0226 (8)0.0183 (8)0.0160 (7)0.0027 (6)0.0019 (6)0.0030 (6)
C40.0216 (8)0.0203 (8)0.0190 (7)0.0009 (6)0.0034 (7)0.0024 (6)
C50.0230 (8)0.0275 (9)0.0257 (8)0.0036 (7)0.0007 (7)0.0049 (7)
C60.0284 (9)0.0196 (9)0.0271 (8)0.0003 (7)0.0014 (7)0.0019 (7)
C70.0332 (10)0.0258 (9)0.0263 (8)0.0046 (8)0.0047 (8)0.0043 (7)
C80.0274 (9)0.0257 (8)0.0281 (8)0.0017 (7)0.0107 (8)0.0006 (7)
C90.0468 (13)0.0418 (12)0.0289 (9)0.0053 (9)0.0040 (9)0.0082 (9)
C100.0246 (8)0.0227 (8)0.0190 (7)0.0027 (7)0.0038 (7)0.0015 (6)
C110.0295 (9)0.0223 (8)0.0317 (9)0.0044 (7)0.0002 (7)0.0032 (7)
C120.0321 (9)0.0210 (8)0.0257 (8)0.0053 (7)0.0086 (7)0.0022 (7)
C130.0486 (12)0.0459 (12)0.0237 (9)0.0094 (10)0.0109 (8)0.0042 (8)
O10.0335 (7)0.0199 (6)0.0226 (6)0.0014 (5)0.0056 (5)0.0032 (5)
O20.0225 (6)0.0198 (6)0.0284 (6)0.0036 (5)0.0016 (5)0.0023 (5)
O30.0280 (6)0.0262 (6)0.0205 (6)0.0012 (5)0.0023 (5)0.0010 (5)
O40.0523 (9)0.0409 (9)0.0367 (8)0.0211 (7)0.0091 (7)0.0027 (7)
O50.0258 (6)0.0183 (5)0.0209 (6)0.0030 (5)0.0037 (5)0.0027 (4)
O60.0300 (7)0.0267 (6)0.0309 (7)0.0054 (5)0.0079 (6)0.0018 (5)
O70.0274 (6)0.0321 (7)0.0166 (5)0.0012 (5)0.0014 (5)0.0010 (5)
O80.0378 (8)0.0497 (9)0.0325 (7)0.0160 (7)0.0052 (6)0.0058 (7)
Geometric parameters (Å, º) top
Cl1—C71.7847 (19)C7—H720.959
C1—C21.513 (2)C8—C91.490 (3)
C1—O11.397 (2)C8—O31.348 (2)
C1—O21.421 (2)C8—O41.186 (2)
C1—H110.955C9—H910.960
C2—C31.515 (2)C9—H920.960
C2—O71.435 (2)C9—H930.960
C2—H210.960C10—C111.487 (2)
C3—C41.516 (2)C10—O51.355 (2)
C3—O51.428 (2)C10—O61.191 (2)
C3—H310.946C11—H1110.960
C4—C51.506 (2)C11—H1120.960
C4—O21.428 (2)C11—H1130.960
C4—H410.950C12—C131.495 (3)
C5—O31.436 (2)C12—O71.348 (2)
C5—H520.961C12—O81.192 (2)
C6—C71.493 (3)C13—H1320.958
C6—O11.422 (2)C13—H1330.960
C6—H620.958
C2—C1—O1106.34 (13)C6—C7—H72108.3
C2—C1—O2105.66 (14)Cl1—C7—H72110.3
O1—C1—O2111.71 (13)C9—C8—O3110.43 (17)
C2—C1—H11114.5C9—C8—O4125.54 (18)
O1—C1—H11108.9O3—C8—O4124.01 (18)
O2—C1—H11109.8C8—C9—H91109.4
C1—C2—C3100.45 (14)C8—C9—H92109.5
C1—C2—O7106.62 (13)H91—C9—H92109.5
C3—C2—O7109.57 (13)C8—C9—H93109.5
C1—C2—H21117.9H91—C9—H93109.5
C3—C2—H21114.2H92—C9—H93109.5
O7—C2—H21107.6C11—C10—O5110.36 (14)
C2—C3—C4102.56 (13)C11—C10—O6127.02 (16)
C2—C3—O5114.33 (13)O5—C10—O6122.62 (16)
C4—C3—O5108.65 (13)C10—C11—H111109.4
C2—C3—H31109.9C10—C11—H112109.6
C4—C3—H31116.8H111—C11—H112109.5
O5—C3—H31105.0C10—C11—H113109.4
C3—C4—C5115.53 (14)H111—C11—H113109.5
C3—C4—O2104.72 (13)H112—C11—H113109.5
C5—C4—O2110.94 (13)C13—C12—O7110.78 (18)
C3—C4—H41109.7C13—C12—O8125.82 (18)
C5—C4—H41101.6O7—C12—O8123.38 (16)
O2—C4—H41114.8C12—C13—H132108.3
C4—C5—O3111.48 (14)C12—C13—H133110.9
C4—C5—H52109.7H132—C13—H133109.9
O3—C5—H52109.5C6—O1—C1113.63 (13)
C7—C6—O1109.42 (15)C4—O2—C1110.50 (12)
C7—C6—H62108.7C5—O3—C8116.57 (14)
O1—C6—H62109.3C3—O5—C10115.77 (13)
C6—C7—Cl1112.03 (13)C2—O7—C12117.38 (14)
Intermolecular C—H···O interactions (Å, °) in (I) top
H···OC···OH—C···O
C1—H11···O4i2.563.453 (2)157
C9—H92···O6ii2.553.447 (3)156
C11—H113···O5iii2.483.428 (2)168
C7—H72···O4iv2.613.391 (3)139
C6—H61···O2v2.713.249 (2)117
Symmetry codes: (i) -1/2+x, 3/2-y, 2-z; (ii) -x, 1/2+y, 3/2-z; (iii) -1/2+x, 1/2-y, 2-z; (iv) x-1, y, z; (v) -1/2+x, 3/2-y, 2-z.
 

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