PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2725.
Published online 2009 October 13. doi:  10.1107/S1600536809040975
PMCID: PMC2971110

Glucosyl anthranilate

Abstract

In the crystal structure of the title compound, C21H25NO11, the hexopyranosyl ring adopts a chair conformation and the five substituents are in equatorial positions. An intra­molecular hydrogen bond between the amino group and a neighbouring carbonyl group is found. Two carbonyl groups are disordered and were refined using a split model.

Related literature

The title compound was first obtained by Robert & Tabone (1953 [triangle]). For the glycosyl­ation reaction of N-hydroxy­phthalimide, see: Cao et al. (1995 [triangle]); Saulius et al. (2005 [triangle]). For the Hofmann rearrangement, see: Aspinall (1941 [triangle]); Yu et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2725-scheme1.jpg

Experimental

Crystal data

  • C21H25NO11
  • M r = 467.42
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2725-efi1.jpg
  • a = 5.8220 (12) Å
  • b = 9.1210 (18) Å
  • c = 11.131 (2) Å
  • α = 98.94 (3)°
  • β = 94.53 (3)°
  • γ = 90.22 (3)°
  • V = 582.0 (2) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: none
  • 2321 measured reflections
  • 2096 independent reflections
  • 1783 reflections with I > 2σ(I)
  • R int = 0.020
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.100
  • S = 1.04
  • 2096 reflections
  • 320 parameters
  • 5 restraints
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040975/nc2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040975/nc2157Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We are grateful to the National Natural Science Foundation of China (No. 30701041)

supplementary crystallographic information

Comment

The title compound was obtained as a by-product of the glycosylation reaction of N-hydroxyphthalimide during the synthesis of O-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)- N-oxyphthalimide (Cao et al., 1995; Saulius et al., 2005). Hofmann rearrangement is considered to be the reaction mechanism for its formation (Aspinall,1941;Yu et al.,2001).

The hexopyranosyl ring adopts a chair configuration and all substitutents are in equatorial positions (Fig. 1). Between the amino H atoms and the neighboured carbonyl oxygen atom intramolecular N-H···O hydrogen bonding is found (Table 1).

Experimental

A mixture of N-hydroxyphthalimide(1.5 g, 9.2 mmol), tetrabutylammonium hydrogen sulfate (TBAHS 0.34 g, 1 mmol) and Na2CO3 (1M, 20 mL) was stirred at room temperature. After one hour a chloroform solution of 2,3,4,6- tetra-O-acetyl-α-D- glucopyranosyl bromide (3.7 g, 9.0 mmol) was added and the mixture was stirred over night. The organic phase was separated, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Afterwards the product was purified by column chromatography on silica gel(ethylacetate: petroleum ether v/v 1:2). Removal of the solvent leads to the title compound. Yield: 0.34 g (8%). Single crystals suitable for X-ray analysis were obtained by recrystallization from EtOAc. m.p. 403–405 K.

Refinement

The H atoms were positioned with idealized geometry (methyl H atoms allowed to rotate but not to tip) and were refined using a riding model. One of the three methyl groups is disordered in two orientations and was refined as disordered group. Two carbonyl groups are disordered and were refined using a split model. Because the absolute structure cannot be determined Friedel opposites were merged in the refinement.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. The bonds to the disordered atoms are shown with dashed lines. H atoms are omitted for clarity.

Crystal data

C21H25NO11Z = 1
Mr = 467.42F(000) = 246
Triclinic, P1Dx = 1.334 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8220 (12) ÅCell parameters from 25 reflections
b = 9.1210 (18) Åθ = 9–12°
c = 11.131 (2) ŵ = 0.11 mm1
α = 98.94 (3)°T = 293 K
β = 94.53 (3)°Block, colourless
γ = 90.22 (3)°0.30 × 0.20 × 0.10 mm
V = 582.0 (2) Å3

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.020
Radiation source: fine-focus sealed tubeθmax = 25.3°, θmin = 1.9°
graphiteh = 0→6
ω/2θ scansk = −10→10
2321 measured reflectionsl = −13→13
2096 independent reflections3 standard reflections every 200 reflections
1783 reflections with I > 2σ(I) intensity decay: 1%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.100w = 1/[σ2(Fo2) + (0.0551P)2 + 0.0615P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2096 reflectionsΔρmin = −0.13 e Å3
320 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
5 restraintsExtinction coefficient: 0.052 (8)
Primary atom site location: structure-invariant direct methods

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 (Å2)

xyzUiso*/UeqOcc. (<1)
O10.4723 (4)0.2186 (3)0.0201 (2)0.0473 (6)
O20.4296 (4)0.0007 (3)−0.1971 (2)0.0552 (6)
O30.6518 (6)−0.1311 (4)−0.3260 (4)0.1014 (13)
O40.6863 (4)0.4159 (3)−0.2092 (2)0.0478 (6)
O51.0705 (5)0.4424 (4)−0.1993 (3)0.0797 (9)
O60.8323 (4)0.6042 (3)0.0311 (2)0.0539 (6)
O70.6443 (18)0.8007 (11)−0.0182 (10)0.089 (3)0.50
O7'0.697 (2)0.7638 (13)−0.0826 (9)0.102 (4)0.50
O80.4552 (5)0.5912 (3)0.1864 (2)0.0642 (7)
O90.715 (3)0.587 (3)0.337 (2)0.172 (11)0.50
O9'0.650 (4)0.562 (2)0.3641 (18)0.138 (8)0.50
O100.3348 (4)0.2984 (3)0.2025 (2)0.0538 (6)
O11−0.0099 (4)0.2080 (3)0.1202 (2)0.0613 (7)
N1−0.2584 (6)0.0580 (5)0.2582 (4)0.0830 (11)
H1A−0.37430.00710.27340.100*
H1B−0.25090.08170.18680.100*
C10.3810 (6)0.3425 (4)0.0908 (3)0.0468 (8)
H1C0.24060.37580.04930.056*
C20.5594 (6)0.4647 (4)0.1187 (3)0.0498 (8)
H2A0.69350.43310.16650.060*
C30.6312 (5)0.5090 (4)0.0013 (3)0.0447 (8)
H3A0.50610.5628−0.03600.054*
C40.6931 (5)0.3744 (4)−0.0887 (3)0.0442 (8)
H4A0.84740.3406−0.06530.053*
C50.5175 (6)0.2470 (4)−0.0987 (3)0.0423 (7)
H5A0.37400.2725−0.14230.051*
C60.6126 (6)0.1085 (4)−0.1660 (3)0.0498 (8)
H6A0.67670.1297−0.23950.060*
H6B0.73440.0707−0.11520.060*
C70.4769 (8)−0.1189 (5)−0.2748 (4)0.0656 (11)
C80.2885 (9)−0.2322 (5)−0.2932 (5)0.0827 (14)
H8A0.2755−0.2799−0.37670.124*
H8B0.1459−0.1852−0.27390.124*
H8C0.3223−0.3049−0.24070.124*
C90.8873 (6)0.4456 (4)−0.2551 (3)0.0527 (9)
C100.8433 (8)0.4856 (5)−0.3784 (4)0.0667 (11)
H10A0.79420.5867−0.37180.100*
H10B0.72510.4214−0.42360.100*
H10C0.98220.4748−0.41990.100*
C110.8326 (8)0.7376 (4)−0.0001 (4)0.0644 (10)
C121.0535 (8)0.8176 (5)0.0358 (5)0.0797 (13)
H12A1.02860.92260.04440.120*0.50
H12B1.15870.7897−0.02560.120*0.50
H12C1.11720.79280.11220.120*0.50
H12D1.17440.74750.04290.120*0.50
H12E1.04430.88040.11290.120*0.50
H12F1.08580.8773−0.02490.120*0.50
C130.5261 (15)0.6275 (7)0.3044 (5)0.104 (2)
C140.3672 (15)0.7450 (8)0.3642 (6)0.140 (3)
H14A0.42080.77420.44830.210*
H14B0.21350.70480.35890.210*
H14C0.36750.82990.32290.210*
C150.1294 (6)0.2281 (4)0.2076 (3)0.0463 (8)
C160.1078 (6)0.1823 (4)0.3258 (3)0.0509 (8)
C170.2779 (7)0.2219 (5)0.4221 (3)0.0662 (11)
H17A0.40590.27710.40930.079*
C180.2601 (8)0.1814 (6)0.5343 (4)0.0797 (13)
H18A0.37560.20770.59670.096*
C190.0679 (8)0.1007 (6)0.5540 (4)0.0797 (13)
H19A0.05420.07270.63000.096*
C20−0.0983 (8)0.0629 (5)0.4637 (4)0.0734 (12)
H20A−0.22590.00930.47920.088*
C21−0.0876 (6)0.1010 (5)0.3469 (4)0.0598 (10)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0441 (13)0.0510 (13)0.0484 (14)−0.0033 (10)0.0031 (10)0.0132 (11)
O20.0537 (14)0.0508 (14)0.0595 (15)−0.0097 (11)0.0062 (11)0.0030 (12)
O30.103 (3)0.079 (2)0.117 (3)−0.0201 (19)0.056 (2)−0.026 (2)
O40.0410 (12)0.0614 (14)0.0442 (13)−0.0013 (10)0.0038 (10)0.0185 (10)
O50.0482 (16)0.115 (3)0.085 (2)0.0004 (16)0.0113 (14)0.0408 (19)
O60.0488 (13)0.0473 (13)0.0660 (15)−0.0081 (10)−0.0006 (11)0.0135 (11)
O70.097 (6)0.059 (5)0.111 (8)−0.001 (4)−0.026 (6)0.027 (6)
O7'0.137 (9)0.074 (7)0.097 (7)−0.030 (6)−0.043 (7)0.048 (6)
O80.0817 (19)0.0653 (17)0.0434 (14)−0.0074 (14)0.0076 (13)0.0007 (12)
O90.195 (14)0.25 (2)0.054 (10)−0.041 (14)−0.044 (11)−0.003 (10)
O9'0.24 (2)0.120 (9)0.045 (7)0.027 (12)−0.037 (9)0.012 (6)
O100.0464 (13)0.0762 (17)0.0416 (13)−0.0096 (12)0.0003 (10)0.0195 (12)
O110.0465 (13)0.0835 (18)0.0562 (15)−0.0085 (12)−0.0038 (12)0.0225 (13)
N10.056 (2)0.113 (3)0.084 (3)−0.024 (2)0.0081 (19)0.029 (2)
C10.0431 (18)0.057 (2)0.0412 (18)−0.0010 (16)0.0010 (14)0.0115 (16)
C20.053 (2)0.055 (2)0.0421 (17)−0.0015 (16)−0.0016 (15)0.0115 (16)
C30.0415 (18)0.0468 (19)0.0463 (19)−0.0008 (15)−0.0011 (14)0.0115 (15)
C40.0395 (17)0.051 (2)0.0440 (18)−0.0010 (15)−0.0026 (14)0.0153 (15)
C50.0365 (16)0.0510 (19)0.0408 (17)−0.0019 (14)0.0005 (13)0.0127 (14)
C60.0476 (19)0.052 (2)0.0501 (19)−0.0045 (16)0.0055 (15)0.0068 (16)
C70.083 (3)0.055 (2)0.057 (2)−0.010 (2)0.007 (2)0.0042 (19)
C80.099 (4)0.064 (3)0.080 (3)−0.028 (3)0.008 (3)−0.005 (2)
C90.050 (2)0.052 (2)0.059 (2)−0.0008 (16)0.0101 (18)0.0132 (17)
C100.074 (3)0.074 (3)0.056 (2)−0.011 (2)0.014 (2)0.019 (2)
C110.076 (3)0.050 (2)0.069 (3)−0.007 (2)0.001 (2)0.0158 (19)
C120.081 (3)0.059 (3)0.099 (4)−0.020 (2)0.016 (3)0.007 (2)
C130.152 (6)0.099 (4)0.052 (3)−0.029 (4)−0.004 (4)−0.006 (3)
C140.209 (8)0.121 (5)0.081 (4)−0.021 (5)0.050 (5)−0.032 (4)
C150.0416 (18)0.049 (2)0.0492 (19)0.0038 (15)0.0062 (15)0.0104 (15)
C160.047 (2)0.059 (2)0.050 (2)0.0088 (16)0.0126 (16)0.0149 (17)
C170.061 (2)0.093 (3)0.048 (2)−0.001 (2)0.0040 (18)0.021 (2)
C180.069 (3)0.121 (4)0.053 (2)0.005 (3)0.006 (2)0.028 (2)
C190.080 (3)0.112 (4)0.060 (3)0.023 (3)0.026 (2)0.041 (2)
C200.067 (3)0.086 (3)0.078 (3)0.004 (2)0.031 (2)0.034 (2)
C210.045 (2)0.070 (2)0.069 (2)0.0069 (18)0.0152 (18)0.021 (2)

Geometric parameters (Å, °)

O1—C11.405 (4)C6—H6A0.9700
O1—C51.430 (4)C6—H6B0.9700
O2—C71.326 (5)C7—C81.485 (6)
O2—C61.432 (4)C8—H8A0.9600
O3—C71.203 (5)C8—H8B0.9600
O4—C91.356 (4)C8—H8C0.9600
O4—C41.447 (4)C9—C101.478 (5)
O5—C91.194 (4)C10—H10A0.9600
O6—C111.316 (4)C10—H10B0.9600
O6—C31.441 (4)C10—H10C0.9600
O7—C111.257 (10)C11—C121.472 (6)
O7'—C111.217 (9)C12—H12A0.9600
O8—C131.335 (6)C12—H12B0.9600
O8—C21.440 (5)C12—H12C0.9600
O9—C131.204 (17)C12—H12D0.9600
O9'—C131.169 (14)C12—H12E0.9600
O10—C151.364 (4)C12—H12F0.9600
O10—C11.409 (4)C13—C141.526 (11)
O11—C151.206 (4)C14—H14A0.9600
N1—C211.357 (5)C14—H14B0.9600
N1—H1A0.8600C14—H14C0.9600
N1—H1B0.8600C15—C161.456 (5)
C1—C21.500 (5)C16—C171.404 (5)
C1—H1C0.9800C16—C211.410 (5)
C2—C31.515 (5)C17—C181.368 (6)
C2—H2A0.9800C17—H17A0.9300
C3—C41.522 (5)C18—C191.388 (7)
C3—H3A0.9800C18—H18A0.9300
C4—C51.530 (4)C19—C201.342 (7)
C4—H4A0.9800C19—H19A0.9300
C5—C61.497 (5)C20—C211.403 (6)
C5—H5A0.9800C20—H20A0.9300
C1—O1—C5112.2 (2)H10B—C10—H10C109.5
C7—O2—C6115.5 (3)O7'—C11—O739.0 (6)
C9—O4—C4118.9 (3)O7'—C11—O6119.0 (6)
C11—O6—C3120.2 (3)O7—C11—O6119.4 (6)
C13—O8—C2117.4 (4)O7'—C11—C12124.0 (7)
C15—O10—C1117.7 (3)O7—C11—C12123.8 (6)
C21—N1—H1A120.0O6—C11—C12112.6 (4)
C21—N1—H1B120.0C11—C12—H12A109.5
H1A—N1—H1B120.0C11—C12—H12B109.5
O1—C1—O10106.7 (3)H12A—C12—H12B109.5
O1—C1—C2109.6 (3)C11—C12—H12C109.5
O10—C1—C2107.4 (3)H12A—C12—H12C109.5
O1—C1—H1C111.0H12B—C12—H12C109.5
O10—C1—H1C111.0C11—C12—H12D109.5
C2—C1—H1C111.0H12A—C12—H12D141.1
O8—C2—C1107.6 (3)H12B—C12—H12D56.3
O8—C2—C3108.0 (3)H12C—C12—H12D56.3
C1—C2—C3110.1 (3)C11—C12—H12E109.5
O8—C2—H2A110.3H12A—C12—H12E56.3
C1—C2—H2A110.3H12B—C12—H12E141.1
C3—C2—H2A110.3H12C—C12—H12E56.3
O6—C3—C2107.8 (3)H12D—C12—H12E109.5
O6—C3—C4108.3 (3)C11—C12—H12F109.5
C2—C3—C4111.6 (3)H12A—C12—H12F56.3
O6—C3—H3A109.7H12B—C12—H12F56.3
C2—C3—H3A109.7H12C—C12—H12F141.1
C4—C3—H3A109.7H12D—C12—H12F109.5
O4—C4—C3108.6 (3)H12E—C12—H12F109.5
O4—C4—C5105.5 (2)O9'—C13—O928 (2)
C3—C4—C5112.4 (3)O9'—C13—O8128.1 (11)
O4—C4—H4A110.1O9—C13—O8117.2 (13)
C3—C4—H4A110.1O9'—C13—C14120.6 (12)
C5—C4—H4A110.1O9—C13—C14131.9 (12)
O1—C5—C6107.8 (3)O8—C13—C14109.1 (7)
O1—C5—C4110.3 (2)C13—C14—H14A109.5
C6—C5—C4109.7 (3)C13—C14—H14B109.5
O1—C5—H5A109.7H14A—C14—H14B109.5
C6—C5—H5A109.7C13—C14—H14C109.5
C4—C5—H5A109.7H14A—C14—H14C109.5
O2—C6—C5108.5 (3)H14B—C14—H14C109.5
O2—C6—H6A110.0O11—C15—O10120.9 (3)
C5—C6—H6A110.0O11—C15—C16126.9 (3)
O2—C6—H6B110.0O10—C15—C16112.2 (3)
C5—C6—H6B110.0C17—C16—C21118.7 (3)
H6A—C6—H6B108.4C17—C16—C15120.6 (3)
O3—C7—O2123.0 (4)C21—C16—C15120.7 (3)
O3—C7—C8124.4 (4)C18—C17—C16121.6 (4)
O2—C7—C8112.5 (4)C18—C17—H17A119.2
C7—C8—H8A109.5C16—C17—H17A119.2
C7—C8—H8B109.5C17—C18—C19119.3 (4)
H8A—C8—H8B109.5C17—C18—H18A120.4
C7—C8—H8C109.5C19—C18—H18A120.4
H8A—C8—H8C109.5C20—C19—C18120.2 (4)
H8B—C8—H8C109.5C20—C19—H19A119.9
O5—C9—O4122.9 (3)C18—C19—H19A119.9
O5—C9—C10126.6 (4)C19—C20—C21122.7 (4)
O4—C9—C10110.5 (3)C19—C20—H20A118.6
C9—C10—H10A109.5C21—C20—H20A118.6
C9—C10—H10B109.5N1—C21—C20120.4 (4)
H10A—C10—H10B109.5N1—C21—C16122.1 (4)
C9—C10—H10C109.5C20—C21—C16117.5 (4)
H10A—C10—H10C109.5
C5—O1—C1—O10177.4 (2)O1—C5—C6—O272.2 (3)
C5—O1—C1—C2−66.6 (3)C4—C5—C6—O2−167.7 (3)
C15—O10—C1—O1−84.7 (3)C6—O2—C7—O3−7.3 (6)
C15—O10—C1—C2157.9 (3)C6—O2—C7—C8174.2 (4)
C13—O8—C2—C1109.3 (4)C4—O4—C9—O5−1.8 (5)
C13—O8—C2—C3−131.8 (4)C4—O4—C9—C10−180.0 (3)
O1—C1—C2—O8177.5 (3)C3—O6—C11—O7'−21.7 (9)
O10—C1—C2—O8−67.0 (3)C3—O6—C11—O723.3 (8)
O1—C1—C2—C360.0 (3)C3—O6—C11—C12−179.0 (3)
O10—C1—C2—C3175.5 (3)C2—O8—C13—O9'−7.0 (19)
C11—O6—C3—C2−124.0 (3)C2—O8—C13—O923.4 (19)
C11—O6—C3—C4115.1 (4)C2—O8—C13—C14−170.0 (4)
O8—C2—C3—O673.9 (3)C1—O10—C15—O11−1.9 (5)
C1—C2—C3—O6−168.8 (3)C1—O10—C15—C16177.2 (3)
O8—C2—C3—C4−167.2 (3)O11—C15—C16—C17−175.7 (4)
C1—C2—C3—C4−49.9 (4)O10—C15—C16—C175.2 (5)
C9—O4—C4—C3101.4 (3)O11—C15—C16—C212.4 (6)
C9—O4—C4—C5−137.9 (3)O10—C15—C16—C21−176.7 (3)
O6—C3—C4—O4−79.8 (3)C21—C16—C17—C181.2 (6)
C2—C3—C4—O4161.6 (2)C15—C16—C17—C18179.3 (4)
O6—C3—C4—C5163.8 (2)C16—C17—C18—C19−0.8 (7)
C2—C3—C4—C545.2 (3)C17—C18—C19—C200.0 (8)
C1—O1—C5—C6−179.8 (3)C18—C19—C20—C210.3 (8)
C1—O1—C5—C460.5 (3)C19—C20—C21—N1178.9 (4)
O4—C4—C5—O1−167.3 (2)C19—C20—C21—C160.1 (7)
C3—C4—C5—O1−49.1 (3)C17—C16—C21—N1−179.6 (4)
O4—C4—C5—C674.1 (3)C15—C16—C21—N12.2 (6)
C3—C4—C5—C6−167.7 (3)C17—C16—C21—C20−0.8 (5)
C7—O2—C6—C5169.0 (3)C15—C16—C21—C20−178.9 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O110.862.062.704 (5)131

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2157).

References

  • Aspinall, S. R. (1941). J Am Chem Soc 63, 2843–2843.
  • Cao, S. D., Tropper, T. D. & Roy, R. (1995). Tetrahedron, 51, 6679–6686.
  • Enraf–Nonius (1994). CAD-4 EXPRESS Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Robert, D. & Tabone, J. (1953). C. R. Acad. Sci.236, 206–208.
  • Saulius, G., Sabine, C., Olivier, R., Richard, L. M., Edith, D., Claude, L. & Pascal, D. (2005). Bioconjug. Chem 16, 1149–1159. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yu, C. Z., Jiang, Y. Y., Liu, B. & Hu, L. Q. (2001). Tetrahedron Lett 42, 1449–1452.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography