Download citation
Download citation
link to html
In the title compound, C18H22Cl3NO11, a novel derivative of L-idopyran­osiduronic acid, the six-membered ring adopts a chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810010895/bt5207sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810010895/bt5207Isup2.hkl
Contains datablock I

CCDC reference: 774363

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Comment top

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.

Related literature top

For background to L-iduronic acids, see: Capila & Linhardt (2002); Jobron & Jacquinet (1998); Lee et al. (2004). For the synthesis of iduronic acid derivatives, see: Yu et al. (2004); Sanjoy et al. (2001); Lubineau et al. (2000); Lohman et al. (2003).

Experimental top

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.

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, displacement ellipsoids are at the 50% level.
[Figure 2] Fig. 2. A packing diagram of the title compound.
Methyl 2,3-di-O-acetyl-4-O-levulinoyl-1-O-(2,2,2-trichloro- 2-iminoethyl)-L-idopyranosiduronate top
Crystal data top
C18H22Cl3NO11Dx = 1.514 Mg m3
Mr = 534.72Cu Kα radiation, λ = 1.54186 Å
Orthorhombic, P212121Cell parameters from 1098 reflections
a = 9.0498 (10) Åθ = 2.2–27.5°
b = 9.7560 (11) ŵ = 4.07 mm1
c = 26.570 (3) ÅT = 173 K
V = 2345.8 (4) Å3Block, colorless
Z = 40.41 × 0.30 × 0.28 mm
F(000) = 1104
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
4259 independent reflections
Radiation source: rotating anode3893 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scans at fixed χ = 45°θmax = 68.2°, θmin = 3.3°
Absorption correction: numerical
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.286, Tmax = 0.395k = 1111
16340 measured reflectionsl = 3231
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-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 reflectionsΔρmax = 0.45 e Å3
302 parametersΔρmin = 0.48 e Å3
0 restraintsAbsolute structure: Flack (1983), 1804 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.023 (18)
Crystal data top
C18H22Cl3NO11V = 2345.8 (4) Å3
Mr = 534.72Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 9.0498 (10) ŵ = 4.07 mm1
b = 9.7560 (11) ÅT = 173 K
c = 26.570 (3) Å0.41 × 0.30 × 0.28 mm
Data collection top
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 = 0.395Rint = 0.047
16340 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.100Δρmax = 0.45 e Å3
S = 1.09Δρmin = 0.48 e Å3
4259 reflectionsAbsolute structure: Flack (1983), 1804 Friedel pairs
302 parametersAbsolute structure parameter: 0.023 (18)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.43622 (11)0.42769 (10)0.00915 (3)0.0470 (2)
Cl20.44529 (14)0.72085 (10)0.00601 (4)0.0578 (3)
Cl30.62102 (10)0.56765 (16)0.06361 (4)0.0664 (3)
O10.2587 (2)0.4459 (2)0.17647 (7)0.0275 (5)
O20.3250 (2)0.4443 (2)0.09152 (8)0.0329 (5)
O30.0181 (2)0.2548 (2)0.14357 (8)0.0332 (5)
O40.0977 (3)0.3313 (3)0.07477 (9)0.0527 (7)
O50.3933 (2)0.1578 (2)0.10987 (8)0.0320 (5)
O60.2917 (3)0.0176 (3)0.06774 (10)0.0488 (7)
O70.1922 (2)0.1967 (2)0.22751 (8)0.0285 (5)
O80.2316 (3)0.0295 (2)0.23558 (11)0.0493 (7)
O90.1750 (4)0.1508 (4)0.35252 (12)0.0780 (11)
O100.3492 (3)0.4899 (3)0.27135 (9)0.0462 (7)
O110.4850 (3)0.2966 (3)0.26989 (8)0.0402 (6)
N10.2424 (3)0.6658 (3)0.08223 (11)0.0411 (7)
H1A0.27610.73510.06300.049*
C10.2099 (3)0.4196 (4)0.12743 (10)0.0284 (7)
H1C0.12570.48270.11980.034*
C20.1588 (3)0.2725 (3)0.11851 (12)0.0280 (7)
H2A0.14700.25580.08160.034*
C30.2619 (3)0.1663 (3)0.14075 (11)0.0269 (7)
H3A0.21170.07510.14190.032*
C40.3162 (4)0.2048 (3)0.19295 (11)0.0260 (7)
H4A0.39710.14160.20380.031*
C50.3679 (4)0.3526 (3)0.19531 (11)0.0271 (7)
H5A0.46090.36280.17540.033*
C60.3286 (4)0.5705 (4)0.06991 (11)0.0315 (7)
C70.4526 (4)0.5722 (4)0.03110 (11)0.0352 (7)
C80.1037 (4)0.2905 (4)0.11727 (13)0.0366 (8)
C90.2403 (4)0.2721 (4)0.14798 (15)0.0458 (10)
H9A0.32710.29310.12730.069*
H9B0.23730.33410.17700.069*
H9C0.24610.17710.15980.069*
C100.3914 (4)0.0610 (4)0.07321 (11)0.0343 (7)
C110.5308 (4)0.0652 (4)0.04323 (13)0.0471 (9)
H11A0.50750.05430.00740.071*
H11B0.59620.00920.05400.071*
H11C0.58020.15350.04850.071*
C120.1578 (4)0.0694 (4)0.24437 (11)0.0323 (7)
C130.0114 (4)0.0687 (4)0.27120 (12)0.0350 (7)
H13A0.01080.00840.29540.042*
H13B0.06740.05110.24620.042*
C140.0258 (4)0.1992 (4)0.29934 (12)0.0349 (8)
H14A0.02910.27620.27510.042*
H14B0.12540.18980.31430.042*
C150.0820 (4)0.2329 (4)0.34006 (13)0.0434 (9)
C160.0726 (6)0.3724 (4)0.36322 (14)0.0572 (12)
H16A0.15190.38320.38810.086*
H16B0.02330.38320.37990.086*
H16C0.08320.44220.33690.086*
C170.3974 (4)0.3918 (3)0.24983 (12)0.0308 (7)
C180.5206 (4)0.3098 (4)0.32281 (13)0.0481 (10)
H18A0.58600.23460.33290.072*
H18B0.42950.30620.34270.072*
H18C0.57050.39750.32860.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0627 (6)0.0425 (5)0.0358 (4)0.0035 (5)0.0135 (4)0.0068 (4)
Cl20.0917 (8)0.0412 (5)0.0405 (5)0.0004 (5)0.0219 (5)0.0099 (4)
Cl30.0339 (5)0.1146 (10)0.0507 (5)0.0158 (6)0.0041 (4)0.0145 (7)
O10.0301 (11)0.0272 (12)0.0252 (10)0.0002 (10)0.0028 (9)0.0002 (9)
O20.0336 (12)0.0322 (13)0.0330 (11)0.0029 (11)0.0122 (10)0.0045 (10)
O30.0228 (12)0.0440 (14)0.0328 (11)0.0007 (11)0.0049 (10)0.0025 (10)
O40.0407 (15)0.079 (2)0.0381 (15)0.0149 (15)0.0022 (12)0.0001 (14)
O50.0287 (12)0.0353 (13)0.0321 (11)0.0007 (10)0.0113 (10)0.0070 (10)
O60.0489 (16)0.0484 (16)0.0492 (15)0.0084 (14)0.0079 (13)0.0188 (13)
O70.0303 (12)0.0276 (12)0.0276 (11)0.0022 (10)0.0105 (10)0.0035 (9)
O80.0546 (17)0.0269 (14)0.0664 (18)0.0040 (13)0.0261 (15)0.0048 (12)
O90.079 (2)0.089 (3)0.067 (2)0.029 (2)0.0329 (19)0.0091 (19)
O100.0583 (17)0.0445 (16)0.0359 (13)0.0033 (14)0.0002 (13)0.0117 (12)
O110.0410 (14)0.0437 (14)0.0358 (12)0.0008 (12)0.0087 (11)0.0005 (11)
N10.052 (2)0.0306 (16)0.0402 (16)0.0008 (16)0.0072 (15)0.0049 (13)
C10.0252 (15)0.0342 (17)0.0259 (14)0.0011 (15)0.0053 (12)0.0028 (15)
C20.0214 (15)0.0346 (18)0.0281 (16)0.0045 (15)0.0052 (13)0.0032 (14)
C30.0249 (16)0.0300 (17)0.0258 (15)0.0021 (14)0.0094 (13)0.0001 (13)
C40.0266 (16)0.0278 (17)0.0236 (15)0.0022 (14)0.0063 (13)0.0010 (13)
C50.0237 (16)0.0273 (16)0.0304 (16)0.0014 (14)0.0025 (14)0.0014 (13)
C60.0374 (17)0.0334 (18)0.0237 (15)0.0014 (17)0.0004 (13)0.0029 (15)
C70.0366 (18)0.0417 (19)0.0273 (15)0.0030 (18)0.0002 (14)0.0004 (15)
C80.0291 (18)0.043 (2)0.0373 (19)0.0020 (17)0.0018 (15)0.0103 (16)
C90.0248 (19)0.055 (2)0.058 (2)0.0024 (18)0.0058 (17)0.006 (2)
C100.0381 (18)0.0355 (18)0.0295 (16)0.0043 (18)0.0005 (14)0.0050 (15)
C110.050 (2)0.050 (2)0.0415 (19)0.002 (2)0.0182 (17)0.0085 (19)
C120.0360 (18)0.0289 (17)0.0319 (16)0.0055 (17)0.0062 (14)0.0035 (15)
C130.0318 (17)0.0350 (18)0.0383 (17)0.0042 (17)0.0068 (14)0.0049 (16)
C140.0305 (18)0.0380 (19)0.0363 (17)0.0014 (16)0.0072 (15)0.0054 (15)
C150.048 (2)0.055 (2)0.0276 (17)0.002 (2)0.0040 (17)0.0029 (17)
C160.075 (3)0.058 (3)0.039 (2)0.008 (2)0.007 (2)0.0088 (18)
C170.0275 (16)0.0347 (19)0.0301 (16)0.0089 (15)0.0022 (14)0.0008 (14)
C180.047 (2)0.065 (3)0.0320 (18)0.011 (2)0.0091 (17)0.0113 (18)
Geometric parameters (Å, º) top
Cl1—C71.776 (4)C4—C51.517 (4)
Cl2—C71.754 (4)C4—H4A1.0000
Cl3—C71.753 (3)C5—C171.522 (4)
O1—C11.399 (3)C5—H5A1.0000
O1—C51.433 (4)C6—C71.524 (4)
O2—C61.359 (4)C8—C91.492 (5)
O2—C11.433 (3)C9—H9A0.9800
O3—C81.351 (4)C9—H9B0.9800
O3—C21.447 (3)C9—H9C0.9800
O4—C81.199 (4)C10—C111.492 (4)
O5—C101.357 (4)C11—H11A0.9800
O5—C31.447 (3)C11—H11B0.9800
O6—C101.194 (4)C11—H11C0.9800
O7—C121.356 (4)C12—C131.504 (4)
O7—C41.452 (3)C13—C141.515 (5)
O8—C121.197 (4)C13—H13A0.9900
O9—C151.208 (5)C13—H13B0.9900
O10—C171.197 (4)C14—C151.493 (5)
O11—C171.333 (4)C14—H14A0.9900
O11—C181.448 (4)C14—H14B0.9900
N1—C61.256 (4)C15—C161.496 (5)
N1—H1A0.9001C16—H16A0.9800
C1—C21.527 (4)C16—H16B0.9800
C1—H1C1.0000C16—H16C0.9800
C2—C31.514 (4)C18—H18A0.9800
C2—H2A1.0000C18—H18B0.9800
C3—C41.518 (4)C18—H18C0.9800
C3—H3A1.0000
C1—O1—C5115.3 (2)C8—C9—H9A109.5
C6—O2—C1116.8 (2)C8—C9—H9B109.5
C8—O3—C2116.7 (2)H9A—C9—H9B109.5
C10—O5—C3115.9 (2)C8—C9—H9C109.5
C12—O7—C4115.9 (2)H9A—C9—H9C109.5
C17—O11—C18117.3 (3)H9B—C9—H9C109.5
C6—N1—H1A101.4O6—C10—O5123.0 (3)
O1—C1—O2111.1 (2)O6—C10—C11126.3 (3)
O1—C1—C2114.3 (3)O5—C10—C11110.7 (3)
O2—C1—C2105.9 (2)C10—C11—H11A109.5
O1—C1—H1C108.4C10—C11—H11B109.5
O2—C1—H1C108.4H11A—C11—H11B109.5
C2—C1—H1C108.4C10—C11—H11C109.5
O3—C2—C3106.3 (2)H11A—C11—H11C109.5
O3—C2—C1107.9 (2)H11B—C11—H11C109.5
C3—C2—C1113.3 (3)O8—C12—O7123.1 (3)
O3—C2—H2A109.7O8—C12—C13125.5 (3)
C3—C2—H2A109.7O7—C12—C13111.3 (3)
C1—C2—H2A109.7C12—C13—C14115.2 (3)
O5—C3—C2108.9 (2)C12—C13—H13A108.5
O5—C3—C4105.4 (2)C14—C13—H13A108.5
C2—C3—C4112.8 (3)C12—C13—H13B108.5
O5—C3—H3A109.9C14—C13—H13B108.5
C2—C3—H3A109.9H13A—C13—H13B107.5
C4—C3—H3A109.9C15—C14—C13113.4 (3)
O7—C4—C5105.3 (2)C15—C14—H14A108.9
O7—C4—C3108.3 (2)C13—C14—H14A108.9
C5—C4—C3111.9 (3)C15—C14—H14B108.9
O7—C4—H4A110.4C13—C14—H14B108.9
C5—C4—H4A110.4H14A—C14—H14B107.7
C3—C4—H4A110.4O9—C15—C14120.5 (4)
O1—C5—C4112.1 (3)O9—C15—C16122.0 (4)
O1—C5—C17107.1 (3)C14—C15—C16117.5 (4)
C4—C5—C17109.4 (3)C15—C16—H16A109.5
O1—C5—H5A109.4C15—C16—H16B109.5
C4—C5—H5A109.4H16A—C16—H16B109.5
C17—C5—H5A109.4C15—C16—H16C109.5
N1—C6—O2123.1 (3)H16A—C16—H16C109.5
N1—C6—C7128.7 (3)H16B—C16—H16C109.5
O2—C6—C7108.2 (3)O10—C17—O11125.6 (3)
C6—C7—Cl3107.9 (2)O10—C17—C5126.3 (3)
C6—C7—Cl2111.2 (3)O11—C17—C5108.1 (3)
Cl3—C7—Cl2109.31 (19)O11—C18—H18A109.5
C6—C7—Cl1109.7 (2)O11—C18—H18B109.5
Cl3—C7—Cl1110.4 (2)H18A—C18—H18B109.5
Cl2—C7—Cl1108.34 (16)O11—C18—H18C109.5
O4—C8—O3122.4 (3)H18A—C18—H18C109.5
O4—C8—C9126.3 (4)H18B—C18—H18C109.5
O3—C8—C9111.2 (3)
C5—O1—C1—O268.1 (3)C3—C4—C5—C17171.0 (3)
C5—O1—C1—C251.8 (3)C1—O2—C6—N14.3 (5)
C6—O2—C1—O194.0 (3)C1—O2—C6—C7176.8 (2)
C6—O2—C1—C2141.3 (3)N1—C6—C7—Cl3108.7 (4)
C8—O3—C2—C3151.7 (3)O2—C6—C7—Cl370.2 (3)
C8—O3—C2—C186.4 (3)N1—C6—C7—Cl211.1 (5)
O1—C1—C2—O372.9 (3)O2—C6—C7—Cl2170.0 (2)
O2—C1—C2—O3164.5 (2)N1—C6—C7—Cl1131.0 (3)
O1—C1—C2—C344.6 (3)O2—C6—C7—Cl150.2 (3)
O2—C1—C2—C378.1 (3)C2—O3—C8—O42.0 (5)
C10—O5—C3—C293.1 (3)C2—O3—C8—C9177.9 (3)
C10—O5—C3—C4145.6 (3)C3—O5—C10—O63.6 (5)
O3—C2—C3—O5167.4 (2)C3—O5—C10—C11178.4 (3)
C1—C2—C3—O574.3 (3)C4—O7—C12—O86.8 (5)
O3—C2—C3—C475.9 (3)C4—O7—C12—C13168.6 (3)
C1—C2—C3—C442.4 (3)O8—C12—C13—C14152.1 (4)
C12—O7—C4—C5159.4 (3)O7—C12—C13—C1432.6 (4)
C12—O7—C4—C380.8 (3)C12—C13—C14—C1561.0 (4)
O5—C3—C4—O7172.2 (2)C13—C14—C15—O99.9 (5)
C2—C3—C4—O769.0 (3)C13—C14—C15—C16168.3 (3)
O5—C3—C4—C572.1 (3)C18—O11—C17—O102.6 (5)
C2—C3—C4—C546.6 (3)C18—O11—C17—C5176.6 (3)
C1—O1—C5—C455.9 (3)O1—C5—C17—O106.6 (4)
C1—O1—C5—C17175.8 (2)C4—C5—C17—O10128.3 (4)
O7—C4—C5—O165.1 (3)O1—C5—C17—O11172.7 (2)
C3—C4—C5—O152.4 (3)C4—C5—C17—O1150.9 (3)
O7—C4—C5—C1753.6 (3)

Experimental details

Crystal data
Chemical formulaC18H22Cl3NO11
Mr534.72
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)9.0498 (10), 9.7560 (11), 26.570 (3)
V3)2345.8 (4)
Z4
Radiation typeCu Kα
µ (mm1)4.07
Crystal size (mm)0.41 × 0.30 × 0.28
Data collection
DiffractometerRigaku R-AXIS RAPID IP area-detector
diffractometer
Absorption correctionNumerical
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.286, 0.395
No. of measured, independent and
observed [I > 2σ(I)] reflections
16340, 4259, 3893
Rint0.047
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.100, 1.09
No. of reflections4259
No. of parameters302
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.48
Absolute structureFlack (1983), 1804 Friedel pairs
Absolute structure parameter0.023 (18)

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds