

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810010895/bt5207sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810010895/bt5207Isup2.hkl |
CCDC reference: 774363
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.100
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 5 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O4 .. 3.09 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl3 .. O9 .. 3.01 Ang. PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
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 68.21 From the CIF: _reflns_number_total 4259 Count of symmetry unique reflns 2455 Completeness (_total/calc) 173.48% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1804 Fraction of Friedel pairs measured 0.735 Are heavy atom types Z>Si present yes PLAT791_ALERT_4_G The Model has Chirality at C1 (Verify) .... S PLAT791_ALERT_4_G The Model has Chirality at C2 (Verify) .... R PLAT791_ALERT_4_G The Model has Chirality at C3 (Verify) .... S PLAT791_ALERT_4_G The Model has Chirality at C4 (Verify) .... R PLAT791_ALERT_4_G The Model has Chirality at C5 (Verify) .... 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 0 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 1 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared in 76.8% yield by treatment with trichloroaceonitrile and DBU at 0 °C. The reaction was stirred for 30 min then allowed to warm to room temperature. Solvent was evaporated and the residue purified by Flash silica gel column chromatography (silica quenched with 1% NEt3) afford the title compound as syrupy.
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95—1.00 Å and Uiso(H) = 1.2—1.5Ueq(C).
Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of the title compound, displacement ellipsoids are at the 50% level. |
![]() | Fig. 2. A packing diagram of the title compound. |
C18H22Cl3NO11 | Dx = 1.514 Mg m−3 |
Mr = 534.72 | Cu Kα radiation, λ = 1.54186 Å |
Orthorhombic, P212121 | Cell parameters from 1098 reflections |
a = 9.0498 (10) Å | θ = 2.2–27.5° |
b = 9.7560 (11) Å | µ = 4.07 mm−1 |
c = 26.570 (3) Å | T = 173 K |
V = 2345.8 (4) Å3 | Block, colorless |
Z = 4 | 0.41 × 0.30 × 0.28 mm |
F(000) = 1104 |
Rigaku R-AXIS RAPID IP area-detector diffractometer | 4259 independent reflections |
Radiation source: rotating anode | 3893 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans at fixed χ = 45° | θmax = 68.2°, θmin = 3.3° |
Absorption correction: numerical (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.286, Tmax = 0.395 | k = −11→11 |
16340 measured reflections | l = −32→31 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0268P)2 + 1.8534P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
4259 reflections | Δρmax = 0.45 e Å−3 |
302 parameters | Δρmin = −0.48 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1804 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.023 (18) |
C18H22Cl3NO11 | V = 2345.8 (4) Å3 |
Mr = 534.72 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 9.0498 (10) Å | µ = 4.07 mm−1 |
b = 9.7560 (11) Å | T = 173 K |
c = 26.570 (3) Å | 0.41 × 0.30 × 0.28 mm |
Rigaku R-AXIS RAPID IP area-detector diffractometer | 4259 independent reflections |
Absorption correction: numerical (ABSCOR; Higashi, 1995) | 3893 reflections with I > 2σ(I) |
Tmin = 0.286, Tmax = 0.395 | Rint = 0.047 |
16340 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.100 | Δρmax = 0.45 e Å−3 |
S = 1.09 | Δρmin = −0.48 e Å−3 |
4259 reflections | Absolute structure: Flack (1983), 1804 Friedel pairs |
302 parameters | Absolute structure parameter: 0.023 (18) |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
Cl1 | 0.43622 (11) | 0.42769 (10) | −0.00915 (3) | 0.0470 (2) | |
Cl2 | 0.44529 (14) | 0.72085 (10) | −0.00601 (4) | 0.0578 (3) | |
Cl3 | 0.62102 (10) | 0.56765 (16) | 0.06361 (4) | 0.0664 (3) | |
O1 | 0.2587 (2) | 0.4459 (2) | 0.17647 (7) | 0.0275 (5) | |
O2 | 0.3250 (2) | 0.4443 (2) | 0.09152 (8) | 0.0329 (5) | |
O3 | 0.0181 (2) | 0.2548 (2) | 0.14357 (8) | 0.0332 (5) | |
O4 | −0.0977 (3) | 0.3313 (3) | 0.07477 (9) | 0.0527 (7) | |
O5 | 0.3933 (2) | 0.1578 (2) | 0.10987 (8) | 0.0320 (5) | |
O6 | 0.2917 (3) | −0.0176 (3) | 0.06774 (10) | 0.0488 (7) | |
O7 | 0.1922 (2) | 0.1967 (2) | 0.22751 (8) | 0.0285 (5) | |
O8 | 0.2316 (3) | −0.0295 (2) | 0.23558 (11) | 0.0493 (7) | |
O9 | 0.1750 (4) | 0.1508 (4) | 0.35252 (12) | 0.0780 (11) | |
O10 | 0.3492 (3) | 0.4899 (3) | 0.27135 (9) | 0.0462 (7) | |
O11 | 0.4850 (3) | 0.2966 (3) | 0.26989 (8) | 0.0402 (6) | |
N1 | 0.2424 (3) | 0.6658 (3) | 0.08223 (11) | 0.0411 (7) | |
H1A | 0.2761 | 0.7351 | 0.0630 | 0.049* | |
C1 | 0.2099 (3) | 0.4196 (4) | 0.12743 (10) | 0.0284 (7) | |
H1C | 0.1257 | 0.4827 | 0.1198 | 0.034* | |
C2 | 0.1588 (3) | 0.2725 (3) | 0.11851 (12) | 0.0280 (7) | |
H2A | 0.1470 | 0.2558 | 0.0816 | 0.034* | |
C3 | 0.2619 (3) | 0.1663 (3) | 0.14075 (11) | 0.0269 (7) | |
H3A | 0.2117 | 0.0751 | 0.1419 | 0.032* | |
C4 | 0.3162 (4) | 0.2048 (3) | 0.19295 (11) | 0.0260 (7) | |
H4A | 0.3971 | 0.1416 | 0.2038 | 0.031* | |
C5 | 0.3679 (4) | 0.3526 (3) | 0.19531 (11) | 0.0271 (7) | |
H5A | 0.4609 | 0.3628 | 0.1754 | 0.033* | |
C6 | 0.3286 (4) | 0.5705 (4) | 0.06991 (11) | 0.0315 (7) | |
C7 | 0.4526 (4) | 0.5722 (4) | 0.03110 (11) | 0.0352 (7) | |
C8 | −0.1037 (4) | 0.2905 (4) | 0.11727 (13) | 0.0366 (8) | |
C9 | −0.2403 (4) | 0.2721 (4) | 0.14798 (15) | 0.0458 (10) | |
H9A | −0.3271 | 0.2931 | 0.1273 | 0.069* | |
H9B | −0.2373 | 0.3341 | 0.1770 | 0.069* | |
H9C | −0.2461 | 0.1771 | 0.1598 | 0.069* | |
C10 | 0.3914 (4) | 0.0610 (4) | 0.07321 (11) | 0.0343 (7) | |
C11 | 0.5308 (4) | 0.0652 (4) | 0.04323 (13) | 0.0471 (9) | |
H11A | 0.5075 | 0.0543 | 0.0074 | 0.071* | |
H11B | 0.5962 | −0.0092 | 0.0540 | 0.071* | |
H11C | 0.5802 | 0.1535 | 0.0485 | 0.071* | |
C12 | 0.1578 (4) | 0.0694 (4) | 0.24437 (11) | 0.0323 (7) | |
C13 | 0.0114 (4) | 0.0687 (4) | 0.27120 (12) | 0.0350 (7) | |
H13A | 0.0108 | −0.0084 | 0.2954 | 0.042* | |
H13B | −0.0674 | 0.0511 | 0.2462 | 0.042* | |
C14 | −0.0258 (4) | 0.1992 (4) | 0.29934 (12) | 0.0349 (8) | |
H14A | −0.0291 | 0.2762 | 0.2751 | 0.042* | |
H14B | −0.1254 | 0.1898 | 0.3143 | 0.042* | |
C15 | 0.0820 (4) | 0.2329 (4) | 0.34006 (13) | 0.0434 (9) | |
C16 | 0.0726 (6) | 0.3724 (4) | 0.36322 (14) | 0.0572 (12) | |
H16A | 0.1519 | 0.3832 | 0.3881 | 0.086* | |
H16B | −0.0233 | 0.3832 | 0.3799 | 0.086* | |
H16C | 0.0832 | 0.4422 | 0.3369 | 0.086* | |
C17 | 0.3974 (4) | 0.3918 (3) | 0.24983 (12) | 0.0308 (7) | |
C18 | 0.5206 (4) | 0.3098 (4) | 0.32281 (13) | 0.0481 (10) | |
H18A | 0.5860 | 0.2346 | 0.3329 | 0.072* | |
H18B | 0.4295 | 0.3062 | 0.3427 | 0.072* | |
H18C | 0.5705 | 0.3975 | 0.3286 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0627 (6) | 0.0425 (5) | 0.0358 (4) | −0.0035 (5) | 0.0135 (4) | −0.0068 (4) |
Cl2 | 0.0917 (8) | 0.0412 (5) | 0.0405 (5) | −0.0004 (5) | 0.0219 (5) | 0.0099 (4) |
Cl3 | 0.0339 (5) | 0.1146 (10) | 0.0507 (5) | −0.0158 (6) | −0.0041 (4) | 0.0145 (7) |
O1 | 0.0301 (11) | 0.0272 (12) | 0.0252 (10) | 0.0002 (10) | 0.0028 (9) | −0.0002 (9) |
O2 | 0.0336 (12) | 0.0322 (13) | 0.0330 (11) | 0.0029 (11) | 0.0122 (10) | 0.0045 (10) |
O3 | 0.0228 (12) | 0.0440 (14) | 0.0328 (11) | −0.0007 (11) | 0.0049 (10) | −0.0025 (10) |
O4 | 0.0407 (15) | 0.079 (2) | 0.0381 (15) | 0.0149 (15) | −0.0022 (12) | −0.0001 (14) |
O5 | 0.0287 (12) | 0.0353 (13) | 0.0321 (11) | −0.0007 (10) | 0.0113 (10) | −0.0070 (10) |
O6 | 0.0489 (16) | 0.0484 (16) | 0.0492 (15) | −0.0084 (14) | 0.0079 (13) | −0.0188 (13) |
O7 | 0.0303 (12) | 0.0276 (12) | 0.0276 (11) | −0.0022 (10) | 0.0105 (10) | 0.0035 (9) |
O8 | 0.0546 (17) | 0.0269 (14) | 0.0664 (18) | 0.0040 (13) | 0.0261 (15) | 0.0048 (12) |
O9 | 0.079 (2) | 0.089 (3) | 0.067 (2) | 0.029 (2) | −0.0329 (19) | −0.0091 (19) |
O10 | 0.0583 (17) | 0.0445 (16) | 0.0359 (13) | 0.0033 (14) | −0.0002 (13) | −0.0117 (12) |
O11 | 0.0410 (14) | 0.0437 (14) | 0.0358 (12) | 0.0008 (12) | −0.0087 (11) | 0.0005 (11) |
N1 | 0.052 (2) | 0.0306 (16) | 0.0402 (16) | 0.0008 (16) | 0.0072 (15) | 0.0049 (13) |
C1 | 0.0252 (15) | 0.0342 (17) | 0.0259 (14) | −0.0011 (15) | 0.0053 (12) | 0.0028 (15) |
C2 | 0.0214 (15) | 0.0346 (18) | 0.0281 (16) | −0.0045 (15) | 0.0052 (13) | −0.0032 (14) |
C3 | 0.0249 (16) | 0.0300 (17) | 0.0258 (15) | −0.0021 (14) | 0.0094 (13) | −0.0001 (13) |
C4 | 0.0266 (16) | 0.0278 (17) | 0.0236 (15) | −0.0022 (14) | 0.0063 (13) | −0.0010 (13) |
C5 | 0.0237 (16) | 0.0273 (16) | 0.0304 (16) | −0.0014 (14) | 0.0025 (14) | 0.0014 (13) |
C6 | 0.0374 (17) | 0.0334 (18) | 0.0237 (15) | 0.0014 (17) | −0.0004 (13) | 0.0029 (15) |
C7 | 0.0366 (18) | 0.0417 (19) | 0.0273 (15) | −0.0030 (18) | −0.0002 (14) | 0.0004 (15) |
C8 | 0.0291 (18) | 0.043 (2) | 0.0373 (19) | −0.0020 (17) | 0.0018 (15) | −0.0103 (16) |
C9 | 0.0248 (19) | 0.055 (2) | 0.058 (2) | −0.0024 (18) | 0.0058 (17) | −0.006 (2) |
C10 | 0.0381 (18) | 0.0355 (18) | 0.0295 (16) | 0.0043 (18) | 0.0005 (14) | −0.0050 (15) |
C11 | 0.050 (2) | 0.050 (2) | 0.0415 (19) | 0.002 (2) | 0.0182 (17) | −0.0085 (19) |
C12 | 0.0360 (18) | 0.0289 (17) | 0.0319 (16) | −0.0055 (17) | 0.0062 (14) | 0.0035 (15) |
C13 | 0.0318 (17) | 0.0350 (18) | 0.0383 (17) | −0.0042 (17) | 0.0068 (14) | 0.0049 (16) |
C14 | 0.0305 (18) | 0.0380 (19) | 0.0363 (17) | 0.0014 (16) | 0.0072 (15) | 0.0054 (15) |
C15 | 0.048 (2) | 0.055 (2) | 0.0276 (17) | 0.002 (2) | 0.0040 (17) | 0.0029 (17) |
C16 | 0.075 (3) | 0.058 (3) | 0.039 (2) | −0.008 (2) | 0.007 (2) | −0.0088 (18) |
C17 | 0.0275 (16) | 0.0347 (19) | 0.0301 (16) | −0.0089 (15) | 0.0022 (14) | −0.0008 (14) |
C18 | 0.047 (2) | 0.065 (3) | 0.0320 (18) | −0.011 (2) | −0.0091 (17) | 0.0113 (18) |
Cl1—C7 | 1.776 (4) | C4—C5 | 1.517 (4) |
Cl2—C7 | 1.754 (4) | C4—H4A | 1.0000 |
Cl3—C7 | 1.753 (3) | C5—C17 | 1.522 (4) |
O1—C1 | 1.399 (3) | C5—H5A | 1.0000 |
O1—C5 | 1.433 (4) | C6—C7 | 1.524 (4) |
O2—C6 | 1.359 (4) | C8—C9 | 1.492 (5) |
O2—C1 | 1.433 (3) | C9—H9A | 0.9800 |
O3—C8 | 1.351 (4) | C9—H9B | 0.9800 |
O3—C2 | 1.447 (3) | C9—H9C | 0.9800 |
O4—C8 | 1.199 (4) | C10—C11 | 1.492 (4) |
O5—C10 | 1.357 (4) | C11—H11A | 0.9800 |
O5—C3 | 1.447 (3) | C11—H11B | 0.9800 |
O6—C10 | 1.194 (4) | C11—H11C | 0.9800 |
O7—C12 | 1.356 (4) | C12—C13 | 1.504 (4) |
O7—C4 | 1.452 (3) | C13—C14 | 1.515 (5) |
O8—C12 | 1.197 (4) | C13—H13A | 0.9900 |
O9—C15 | 1.208 (5) | C13—H13B | 0.9900 |
O10—C17 | 1.197 (4) | C14—C15 | 1.493 (5) |
O11—C17 | 1.333 (4) | C14—H14A | 0.9900 |
O11—C18 | 1.448 (4) | C14—H14B | 0.9900 |
N1—C6 | 1.256 (4) | C15—C16 | 1.496 (5) |
N1—H1A | 0.9001 | C16—H16A | 0.9800 |
C1—C2 | 1.527 (4) | C16—H16B | 0.9800 |
C1—H1C | 1.0000 | C16—H16C | 0.9800 |
C2—C3 | 1.514 (4) | C18—H18A | 0.9800 |
C2—H2A | 1.0000 | C18—H18B | 0.9800 |
C3—C4 | 1.518 (4) | C18—H18C | 0.9800 |
C3—H3A | 1.0000 | ||
C1—O1—C5 | 115.3 (2) | C8—C9—H9A | 109.5 |
C6—O2—C1 | 116.8 (2) | C8—C9—H9B | 109.5 |
C8—O3—C2 | 116.7 (2) | H9A—C9—H9B | 109.5 |
C10—O5—C3 | 115.9 (2) | C8—C9—H9C | 109.5 |
C12—O7—C4 | 115.9 (2) | H9A—C9—H9C | 109.5 |
C17—O11—C18 | 117.3 (3) | H9B—C9—H9C | 109.5 |
C6—N1—H1A | 101.4 | O6—C10—O5 | 123.0 (3) |
O1—C1—O2 | 111.1 (2) | O6—C10—C11 | 126.3 (3) |
O1—C1—C2 | 114.3 (3) | O5—C10—C11 | 110.7 (3) |
O2—C1—C2 | 105.9 (2) | C10—C11—H11A | 109.5 |
O1—C1—H1C | 108.4 | C10—C11—H11B | 109.5 |
O2—C1—H1C | 108.4 | H11A—C11—H11B | 109.5 |
C2—C1—H1C | 108.4 | C10—C11—H11C | 109.5 |
O3—C2—C3 | 106.3 (2) | H11A—C11—H11C | 109.5 |
O3—C2—C1 | 107.9 (2) | H11B—C11—H11C | 109.5 |
C3—C2—C1 | 113.3 (3) | O8—C12—O7 | 123.1 (3) |
O3—C2—H2A | 109.7 | O8—C12—C13 | 125.5 (3) |
C3—C2—H2A | 109.7 | O7—C12—C13 | 111.3 (3) |
C1—C2—H2A | 109.7 | C12—C13—C14 | 115.2 (3) |
O5—C3—C2 | 108.9 (2) | C12—C13—H13A | 108.5 |
O5—C3—C4 | 105.4 (2) | C14—C13—H13A | 108.5 |
C2—C3—C4 | 112.8 (3) | C12—C13—H13B | 108.5 |
O5—C3—H3A | 109.9 | C14—C13—H13B | 108.5 |
C2—C3—H3A | 109.9 | H13A—C13—H13B | 107.5 |
C4—C3—H3A | 109.9 | C15—C14—C13 | 113.4 (3) |
O7—C4—C5 | 105.3 (2) | C15—C14—H14A | 108.9 |
O7—C4—C3 | 108.3 (2) | C13—C14—H14A | 108.9 |
C5—C4—C3 | 111.9 (3) | C15—C14—H14B | 108.9 |
O7—C4—H4A | 110.4 | C13—C14—H14B | 108.9 |
C5—C4—H4A | 110.4 | H14A—C14—H14B | 107.7 |
C3—C4—H4A | 110.4 | O9—C15—C14 | 120.5 (4) |
O1—C5—C4 | 112.1 (3) | O9—C15—C16 | 122.0 (4) |
O1—C5—C17 | 107.1 (3) | C14—C15—C16 | 117.5 (4) |
C4—C5—C17 | 109.4 (3) | C15—C16—H16A | 109.5 |
O1—C5—H5A | 109.4 | C15—C16—H16B | 109.5 |
C4—C5—H5A | 109.4 | H16A—C16—H16B | 109.5 |
C17—C5—H5A | 109.4 | C15—C16—H16C | 109.5 |
N1—C6—O2 | 123.1 (3) | H16A—C16—H16C | 109.5 |
N1—C6—C7 | 128.7 (3) | H16B—C16—H16C | 109.5 |
O2—C6—C7 | 108.2 (3) | O10—C17—O11 | 125.6 (3) |
C6—C7—Cl3 | 107.9 (2) | O10—C17—C5 | 126.3 (3) |
C6—C7—Cl2 | 111.2 (3) | O11—C17—C5 | 108.1 (3) |
Cl3—C7—Cl2 | 109.31 (19) | O11—C18—H18A | 109.5 |
C6—C7—Cl1 | 109.7 (2) | O11—C18—H18B | 109.5 |
Cl3—C7—Cl1 | 110.4 (2) | H18A—C18—H18B | 109.5 |
Cl2—C7—Cl1 | 108.34 (16) | O11—C18—H18C | 109.5 |
O4—C8—O3 | 122.4 (3) | H18A—C18—H18C | 109.5 |
O4—C8—C9 | 126.3 (4) | H18B—C18—H18C | 109.5 |
O3—C8—C9 | 111.2 (3) | ||
C5—O1—C1—O2 | −68.1 (3) | C3—C4—C5—C17 | 171.0 (3) |
C5—O1—C1—C2 | 51.8 (3) | C1—O2—C6—N1 | 4.3 (5) |
C6—O2—C1—O1 | −94.0 (3) | C1—O2—C6—C7 | −176.8 (2) |
C6—O2—C1—C2 | 141.3 (3) | N1—C6—C7—Cl3 | 108.7 (4) |
C8—O3—C2—C3 | −151.7 (3) | O2—C6—C7—Cl3 | −70.2 (3) |
C8—O3—C2—C1 | 86.4 (3) | N1—C6—C7—Cl2 | −11.1 (5) |
O1—C1—C2—O3 | 72.9 (3) | O2—C6—C7—Cl2 | 170.0 (2) |
O2—C1—C2—O3 | −164.5 (2) | N1—C6—C7—Cl1 | −131.0 (3) |
O1—C1—C2—C3 | −44.6 (3) | O2—C6—C7—Cl1 | 50.2 (3) |
O2—C1—C2—C3 | 78.1 (3) | C2—O3—C8—O4 | 2.0 (5) |
C10—O5—C3—C2 | −93.1 (3) | C2—O3—C8—C9 | −177.9 (3) |
C10—O5—C3—C4 | 145.6 (3) | C3—O5—C10—O6 | −3.6 (5) |
O3—C2—C3—O5 | 167.4 (2) | C3—O5—C10—C11 | 178.4 (3) |
C1—C2—C3—O5 | −74.3 (3) | C4—O7—C12—O8 | 6.8 (5) |
O3—C2—C3—C4 | −75.9 (3) | C4—O7—C12—C13 | −168.6 (3) |
C1—C2—C3—C4 | 42.4 (3) | O8—C12—C13—C14 | 152.1 (4) |
C12—O7—C4—C5 | −159.4 (3) | O7—C12—C13—C14 | −32.6 (4) |
C12—O7—C4—C3 | 80.8 (3) | C12—C13—C14—C15 | −61.0 (4) |
O5—C3—C4—O7 | −172.2 (2) | C13—C14—C15—O9 | −9.9 (5) |
C2—C3—C4—O7 | 69.0 (3) | C13—C14—C15—C16 | 168.3 (3) |
O5—C3—C4—C5 | 72.1 (3) | C18—O11—C17—O10 | 2.6 (5) |
C2—C3—C4—C5 | −46.6 (3) | C18—O11—C17—C5 | −176.6 (3) |
C1—O1—C5—C4 | −55.9 (3) | O1—C5—C17—O10 | −6.6 (4) |
C1—O1—C5—C17 | −175.8 (2) | C4—C5—C17—O10 | −128.3 (4) |
O7—C4—C5—O1 | −65.1 (3) | O1—C5—C17—O11 | 172.7 (2) |
C3—C4—C5—O1 | 52.4 (3) | C4—C5—C17—O11 | 50.9 (3) |
O7—C4—C5—C17 | 53.6 (3) |
Experimental details
Crystal data | |
Chemical formula | C18H22Cl3NO11 |
Mr | 534.72 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 9.0498 (10), 9.7560 (11), 26.570 (3) |
V (Å3) | 2345.8 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 4.07 |
Crystal size (mm) | 0.41 × 0.30 × 0.28 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP area-detector diffractometer |
Absorption correction | Numerical (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.286, 0.395 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16340, 4259, 3893 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.100, 1.09 |
No. of reflections | 4259 |
No. of parameters | 302 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.48 |
Absolute structure | Flack (1983), 1804 Friedel pairs |
Absolute structure parameter | 0.023 (18) |
Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).
L-iduronic acids are key components of numerous biologically potent oligosaccharides and glycopeptides (Capila & Linhardt, 2002). For example, heparin, heparan sulfate (Jobron & Jacquinet, 1998), dermatan sulfate (Lee et al., 2004). This series of glycosaminoglycans plays an important role in a diverse set of biological processes which all contain L-idopyranosiduronic acids. To study the structure-activity relationship of such polymers, there is a need for chemically pure oligosaccharide sequences which can be prepared by organic syntheses.
Since iduronic acid itself is not commercially available, syntheses of iduronic acid derivatives (Yu et al., 2004) from a variety of starting materials, including idose, glucose, glycals,and glucuronic acid have been developed (Lubineau et al., 2000 & Lohman et al., 2003). Herein, we have explored a novel and efficient route toward the synthesis of L-idopyranosiduronate trichloroacetimidate which will be used as a key building block to synthesize dermatan sulfate.