PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o265.
Published online 2007 December 12. doi:  10.1107/S1600536807065853
PMCID: PMC2915321

Dipropyl 4,8-dioxo-1H,5H-2,6-dioxa-3a,4a,7a,8a-tetra­azacyclo­penta­[def]fluorene-8b,8c-dicarboxyl­ate

Abstract

The title compound, C16H22N4O8, is a glycoluril derivative with two propoxycarbonyl substituents on the convex face of the glycoluril system. The dihedral angle between the five-membered rings in the glycoluril unit is 72.70 (2)°. The oxadiazinane six-membered ring displays a normal chair conformation. One of the propyl groups is disordered over two positions with site occupancies of 0.557 (7) and 0.443 (7). Inter­molecular C—H(...)O hydrogen bonds are effective in the stabilization of the crystal structure.

Related literature

For related structures, see: Branda et al. (1995 [triangle]); Elemans et al. (1999 [triangle]); Gao & Sun (2007 [triangle]); Isaacs & Witt (2002 [triangle]); Isaacs et al. (1999 [triangle]); Li et al. (2007 [triangle]); Rebek (1999 [triangle]); Rowan et al. (1999 [triangle]); She & Xi (2007 [triangle]); Witt et al. (2000 [triangle]); Wu et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o265-scheme1.jpg

Experimental

Crystal data

  • C16H22N4O8
  • M r = 398.38
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o265-efi1.jpg
  • a = 8.6399 (4) Å
  • b = 13.401 (7) Å
  • c = 16.0445 (8) Å
  • V = 1857.7 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 294 (2) K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: none
  • 17272 measured reflections
  • 2315 independent reflections
  • 1967 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.123
  • S = 1.07
  • 2315 reflections
  • 263 parameters
  • 4 restraints
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL (Bruker, 2001 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065853/is2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065853/is2262Isup2.hkl

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

Acknowledgments

The authors thank Dr She Neng-Fang and Meng Xiang-Gao for the data collection.

supplementary crystallographic information

Comment

Glycolurils are a topic of numerous reports; these compounds are of use in supramolecular chemistry as building blocks for molecular clips (Rowan et al., 1999; Isaacs & Witt, 2002) and molecular capsules (Rebek, 1999). The derivatives of glycoluril have been employed in many applications, including polymer cross-linking, explosives and combinational chemistry (Witt et al., 2000). The widespread interest in glycolurils has led to a variety of crystal structures reported for a number of its derivatives. Here we report the structure of the title glycoluril derivative, (I) (Fig. 1), which is an important intermediate for the preparation glycoluril receptors (Wu et al., 2002) and in which the bond lengths and angles present no unusual features and are similar to those found in other similar compounds (Gao & Sun, 2007; She & Xi, 2007; Li et al., 2007).

The oxadiazinane six-membered ring displays a normal chair conformation. The weak intermolecular C—H···O hydrogen bonds cause the formation of a three-dimensional network structure (Fig. 2).

Experimental

The title compound was synthesized according to the procedure reported (Isaacs et al., 1999). Crystals appropriate for X-ray data collection were obtained by slow evaporation of a dichloromethane solution at 283 K.

Refinement

All H atoms were positioned geometrically, with C—H = 0.97 and 0.96 Å for methylene and methyl groups, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). One of the propyl groups is disordered over two positions and the final occupancies refined to 0.557 (7) and 0.443 (7). C15—C16 and C15'-C16' bond lengths were restrained to be 1.54 (1) Å, and C14—C15 and C14'-C15' to be 1.45 (1) Å. Same displacement parameters were used for atoms C15 and C15', and for atoms C16 and C16'. In the absence of significant anomalous scattering effects, Friedel pairs have been merged.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level.
Fig. 2.
A packing diagram of the title compound. C—H···O hydrogen bonds are shown as dashed lines. H atoms not involved in the hydrogen-bonds have been omitted for clarity.

Crystal data

C16H22N4O8F000 = 840
Mr = 398.38Dx = 1.424 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3466 reflections
a = 8.6399 (4) Åθ = 2.5–21.5º
b = 13.401 (7) ŵ = 0.12 mm1
c = 16.0445 (8) ÅT = 294 (2) K
V = 1857.7 (10) Å3Block, colorless
Z = 40.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer1967 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Monochromator: graphiteθmax = 27.0º
T = 294(2) Kθmin = 2.5º
[var phi] and ω scansh = −11→9
Absorption correction: nonek = −16→17
17272 measured reflectionsl = −19→20
2315 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.123  w = 1/[σ2(Fo2) + (0.0681P)2 + 0.2494P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
2315 reflectionsΔρmax = 0.26 e Å3
263 parametersΔρmin = −0.18 e Å3
4 restraintsExtinction correction: none
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)
C10.4167 (4)0.2297 (2)0.2432 (2)0.0501 (8)
H1A0.36800.29060.22390.060*
H1B0.36510.17390.21650.060*
C20.4676 (4)0.1327 (2)0.3595 (2)0.0539 (9)
H2A0.41690.07600.33380.065*
H2B0.45320.12780.41930.065*
C30.6597 (3)0.31946 (18)0.22249 (17)0.0357 (6)
C40.7391 (4)0.1724 (2)0.3941 (2)0.0484 (8)
C50.9211 (4)0.3717 (2)0.2653 (3)0.0605 (10)
H5A1.02360.35990.24270.073*
H5B0.88840.43800.24870.073*
C60.9781 (5)0.2689 (3)0.3785 (3)0.0685 (11)
H6A0.98510.26620.43880.082*
H6B1.08040.25640.35590.082*
C70.6721 (3)0.14966 (18)0.25409 (16)0.0325 (6)
C80.6681 (3)0.05026 (18)0.20526 (17)0.0356 (6)
C90.5560 (5)−0.0444 (2)0.0969 (2)0.0569 (9)
H9A0.5447−0.10000.13520.068*
H9B0.6490−0.05490.06420.068*
C100.4189 (6)−0.0385 (3)0.0411 (3)0.0821 (13)
H10A0.3995−0.10450.01870.098*
H10B0.3299−0.02020.07460.098*
C110.4299 (8)0.0317 (5)−0.0287 (4)0.116 (2)
H11A0.42630.0988−0.00800.174*
H11B0.34480.0209−0.06620.174*
H11C0.52560.0212−0.05780.174*
C120.8373 (3)0.19597 (19)0.26092 (18)0.0350 (6)
C130.9645 (4)0.1474 (2)0.2084 (2)0.0426 (7)
C141.0282 (6)0.1060 (3)0.0683 (3)0.0803 (14)
H14A1.07580.04550.08930.096*0.557 (7)
H14B1.10910.15410.05660.096*0.557 (7)
H14C1.01860.03390.06640.096*0.443 (7)
H14D1.13370.12220.08380.096*0.443 (7)
C150.9389 (12)0.0845 (6)−0.0080 (5)0.094 (3)0.557 (7)
H15A0.86910.02940.00330.113*0.557 (7)
H15B1.01010.0630−0.05110.113*0.557 (7)
C160.844 (2)0.1729 (11)−0.0413 (12)0.130 (5)0.557 (7)
H16A0.75470.1828−0.00650.194*0.557 (7)
H16B0.81090.1589−0.09730.194*0.557 (7)
H16C0.90640.2320−0.04100.194*0.557 (7)
C15'0.9949 (14)0.1470 (8)−0.0134 (5)0.094 (3)0.443 (7)
H15C1.07050.1237−0.05370.113*0.443 (7)
H15D0.99840.2193−0.01170.113*0.443 (7)
C16'0.833 (2)0.1113 (16)−0.0377 (16)0.130 (5)0.443 (7)
H16D0.82190.0418−0.02450.194*0.443 (7)
H16E0.81730.1209−0.09640.194*0.443 (7)
H16F0.75660.1490−0.00740.194*0.443 (7)
N10.5792 (3)0.23013 (15)0.21957 (15)0.0347 (5)
N20.6315 (3)0.13036 (17)0.34032 (15)0.0426 (6)
N30.8136 (3)0.29806 (16)0.23239 (16)0.0390 (6)
N40.8717 (3)0.1929 (2)0.34926 (16)0.0471 (6)
O10.3994 (3)0.22198 (15)0.33015 (16)0.0533 (6)
O20.9261 (3)0.36549 (18)0.35326 (18)0.0682 (7)
O30.6044 (3)0.40152 (14)0.21303 (15)0.0511 (6)
O40.7212 (4)0.1841 (2)0.46809 (15)0.0726 (8)
O50.7493 (3)−0.01743 (15)0.22604 (17)0.0561 (6)
O60.5676 (3)0.05015 (13)0.14370 (13)0.0442 (5)
O71.0852 (3)0.11865 (18)0.23472 (19)0.0643 (7)
O80.9201 (3)0.14622 (19)0.12965 (14)0.0631 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0357 (17)0.0445 (16)0.070 (2)0.0030 (13)−0.0040 (16)−0.0090 (14)
C20.058 (2)0.0406 (15)0.063 (2)−0.0100 (15)0.0269 (18)−0.0051 (14)
C30.0426 (17)0.0291 (12)0.0355 (14)0.0015 (11)0.0017 (13)0.0004 (10)
C40.066 (2)0.0432 (16)0.0356 (17)0.0154 (15)−0.0011 (16)0.0018 (12)
C50.046 (2)0.0427 (16)0.093 (3)−0.0112 (14)0.003 (2)−0.0124 (17)
C60.054 (2)0.075 (2)0.076 (3)0.0048 (19)−0.026 (2)−0.023 (2)
C70.0319 (15)0.0294 (12)0.0362 (14)0.0018 (10)0.0036 (12)−0.0029 (10)
C80.0348 (15)0.0306 (12)0.0413 (16)0.0015 (11)0.0051 (13)−0.0027 (11)
C90.076 (3)0.0388 (15)0.056 (2)−0.0057 (17)0.0001 (19)−0.0154 (14)
C100.076 (3)0.081 (3)0.089 (3)−0.009 (2)−0.007 (3)−0.036 (2)
C110.133 (5)0.117 (4)0.099 (4)0.021 (4)−0.035 (4)−0.004 (3)
C120.0306 (15)0.0321 (12)0.0421 (15)0.0002 (11)−0.0016 (12)−0.0021 (11)
C130.0306 (16)0.0367 (13)0.060 (2)0.0026 (12)0.0053 (14)−0.0013 (13)
C140.085 (3)0.081 (3)0.075 (3)0.026 (2)0.043 (3)−0.002 (2)
C150.126 (7)0.078 (5)0.079 (5)−0.022 (4)0.064 (5)−0.015 (4)
C160.151 (8)0.170 (15)0.068 (4)0.011 (13)0.023 (5)−0.002 (12)
C15'0.126 (7)0.078 (5)0.079 (5)−0.022 (4)0.064 (5)−0.015 (4)
C16'0.151 (8)0.170 (15)0.068 (4)0.011 (13)0.023 (5)−0.002 (12)
N10.0300 (12)0.0312 (10)0.0429 (13)0.0033 (9)−0.0012 (11)−0.0021 (9)
N20.0523 (16)0.0358 (11)0.0397 (13)−0.0004 (11)0.0086 (12)0.0027 (10)
N30.0336 (13)0.0293 (10)0.0542 (14)−0.0028 (9)0.0012 (11)−0.0011 (10)
N40.0431 (15)0.0521 (14)0.0461 (15)0.0096 (12)−0.0126 (13)−0.0050 (12)
O10.0414 (13)0.0464 (11)0.0721 (16)−0.0010 (10)0.0205 (11)−0.0158 (10)
O20.0538 (16)0.0610 (14)0.0899 (19)−0.0064 (12)−0.0132 (15)−0.0325 (13)
O30.0548 (15)0.0308 (9)0.0676 (14)0.0080 (9)−0.0019 (12)0.0057 (9)
O40.098 (2)0.0832 (17)0.0361 (13)0.0226 (17)−0.0014 (14)0.0007 (12)
O50.0535 (13)0.0359 (10)0.0788 (16)0.0124 (10)−0.0078 (13)−0.0107 (10)
O60.0537 (13)0.0353 (9)0.0435 (11)−0.0003 (9)−0.0031 (11)−0.0082 (8)
O70.0360 (14)0.0604 (14)0.0966 (19)0.0096 (11)−0.0057 (14)−0.0154 (13)
O80.0587 (16)0.0793 (16)0.0515 (14)0.0268 (13)0.0173 (13)−0.0024 (12)

Geometric parameters (Å, °)

C1—O11.407 (4)C9—H9B0.9700
C1—N11.454 (4)C10—C111.467 (7)
C1—H1A0.9700C10—H10A0.9700
C1—H1B0.9700C10—H10B0.9700
C2—O11.414 (4)C11—H11A0.9600
C2—N21.449 (4)C11—H11B0.9600
C2—H2A0.9700C11—H11C0.9600
C2—H2B0.9700C12—N41.449 (4)
C3—O31.209 (3)C12—N31.457 (3)
C3—N31.369 (4)C12—C131.530 (4)
C3—N11.385 (3)C13—O71.189 (4)
C4—O41.207 (4)C13—O81.321 (4)
C4—N41.381 (5)C14—C15'1.450 (8)
C4—N21.388 (4)C14—O81.460 (4)
C5—O21.414 (5)C14—C151.475 (8)
C5—N31.455 (4)C14—H14A0.9700
C5—H5A0.9700C14—H14B0.9700
C5—H5B0.9700C14—H14C0.9700
C6—O21.429 (5)C14—H14D0.9700
C6—N41.450 (4)C15—C161.538 (9)
C6—H6A0.9700C15—H15A0.9700
C6—H6B0.9700C15—H15B0.9700
C7—N21.451 (4)C16—H16A0.9600
C7—N11.454 (3)C16—H16B0.9600
C7—C81.546 (3)C16—H16C0.9600
C7—C121.561 (4)C15'—C16'1.532 (10)
C8—O51.194 (3)C15'—H15C0.9700
C8—O61.315 (3)C15'—H15D0.9700
C9—O61.477 (3)C16'—H16D0.9600
C9—C101.486 (6)C16'—H16E0.9600
C9—H9A0.9700C16'—H16F0.9600
O1—C1—N1111.2 (3)N3—C12—C13109.1 (2)
O1—C1—H1A109.4N4—C12—C7104.2 (2)
N1—C1—H1A109.4N3—C12—C7102.9 (2)
O1—C1—H1B109.4C13—C12—C7116.7 (2)
N1—C1—H1B109.4O7—C13—O8126.1 (3)
H1A—C1—H1B108.0O7—C13—C12124.9 (3)
O1—C2—N2110.8 (3)O8—C13—C12108.9 (3)
O1—C2—H2A109.5C15'—C14—O8110.1 (5)
N2—C2—H2A109.5O8—C14—C15107.3 (5)
O1—C2—H2B109.5C15'—C14—H14A135.6
N2—C2—H2B109.5O8—C14—H14A110.3
H2A—C2—H2B108.1C15—C14—H14A110.3
O3—C3—N3126.1 (3)C15'—C14—H14B73.5
O3—C3—N1125.7 (3)O8—C14—H14B110.3
N3—C3—N1108.1 (2)C15—C14—H14B110.3
O4—C4—N4126.4 (4)H14A—C14—H14B108.5
O4—C4—N2125.3 (4)C15'—C14—H14C109.4
N4—C4—N2108.2 (3)O8—C14—H14C109.5
O2—C5—N3110.0 (3)C15'—C14—H14D109.4
O2—C5—H5A109.7O8—C14—H14D110.2
N3—C5—H5A109.7H14C—C14—H14D108.1
O2—C5—H5B109.7C14—C15—C16114.7 (9)
N3—C5—H5B109.7C16—C15—H14C148.2
H5A—C5—H5B108.2C14—C15—H15A108.6
O2—C6—N4110.2 (3)C16—C15—H15A108.6
O2—C6—H6A109.6H14C—C15—H15A78.3
N4—C6—H6A109.6C14—C15—H15B108.6
O2—C6—H6B109.6C16—C15—H15B108.6
N4—C6—H6B109.6H14C—C15—H15B98.0
H6A—C6—H6B108.1H15A—C15—H15B107.6
N2—C7—N1111.2 (2)C14—C15'—C16'107.1 (12)
N2—C7—C8108.9 (2)C14—C15'—H15C110.3
N1—C7—C8115.7 (2)C16'—C15'—H15C110.3
N2—C7—C12103.0 (2)C14—C15'—H15D110.3
N1—C7—C12103.7 (2)C16'—C15'—H15D110.3
C8—C7—C12113.5 (2)H15C—C15'—H15D108.6
O5—C8—O6126.6 (2)C15'—C16'—H16D109.5
O5—C8—C7120.0 (3)C15'—C16'—H16E109.5
O6—C8—C7113.3 (2)H16D—C16'—H16E109.5
O6—C9—C10108.3 (3)C15'—C16'—H16F109.5
O6—C9—H9A110.0H16D—C16'—H16F109.5
C10—C9—H9A110.0H16E—C16'—H16F109.5
O6—C9—H9B110.0C3—N1—C1118.7 (2)
C10—C9—H9B110.0C3—N1—C7110.5 (2)
H9A—C9—H9B108.4C1—N1—C7115.5 (2)
C11—C10—C9116.3 (4)C4—N2—C2120.9 (3)
C11—C10—H10A108.2C4—N2—C7111.0 (2)
C9—C10—H10A108.2C2—N2—C7115.8 (3)
C11—C10—H10B108.2C3—N3—C5121.3 (2)
C9—C10—H10B108.2C3—N3—C12111.7 (2)
H10A—C10—H10B107.4C5—N3—C12115.7 (2)
C10—C11—H11A109.5C4—N4—C12110.2 (3)
C10—C11—H11B109.5C4—N4—C6119.8 (3)
H11A—C11—H11B109.5C12—N4—C6115.3 (3)
C10—C11—H11C109.5C1—O1—C2110.4 (2)
H11A—C11—H11C109.5C5—O2—C6110.2 (3)
H11B—C11—H11C109.5C8—O6—C9115.3 (2)
N4—C12—N3111.3 (2)C13—O8—C14117.6 (3)
N4—C12—C13112.3 (2)
N2—C7—C8—O5−59.0 (4)O1—C2—N2—C7−51.7 (3)
N1—C7—C8—O5174.8 (3)N1—C7—N2—C4−101.6 (3)
C12—C7—C8—O555.1 (4)C8—C7—N2—C4129.7 (2)
N2—C7—C8—O6119.5 (3)C12—C7—N2—C48.9 (3)
N1—C7—C8—O6−6.6 (3)N1—C7—N2—C241.1 (3)
C12—C7—C8—O6−126.4 (3)C8—C7—N2—C2−87.6 (3)
O6—C9—C10—C1169.0 (5)C12—C7—N2—C2151.7 (2)
N2—C7—C12—N42.4 (2)O3—C3—N3—C525.0 (5)
N1—C7—C12—N4118.5 (2)N1—C3—N3—C5−158.9 (3)
C8—C7—C12—N4−115.2 (2)O3—C3—N3—C12167.0 (3)
N2—C7—C12—N3−113.8 (2)N1—C3—N3—C12−17.0 (3)
N1—C7—C12—N32.3 (3)O2—C5—N3—C388.6 (3)
C8—C7—C12—N3128.6 (2)O2—C5—N3—C12−52.0 (4)
N2—C7—C12—C13126.8 (2)N4—C12—N3—C3−102.3 (3)
N1—C7—C12—C13−117.1 (2)C13—C12—N3—C3133.3 (3)
C8—C7—C12—C139.2 (3)C7—C12—N3—C38.7 (3)
N4—C12—C13—O7−6.8 (4)N4—C12—N3—C542.0 (4)
N3—C12—C13—O7117.0 (3)C13—C12—N3—C5−82.4 (3)
C7—C12—C13—O7−127.0 (3)C7—C12—N3—C5153.0 (3)
N4—C12—C13—O8175.3 (2)O4—C4—N4—C12−164.3 (3)
N3—C12—C13—O8−60.8 (3)N2—C4—N4—C1219.2 (3)
C7—C12—C13—O855.1 (3)O4—C4—N4—C6−27.0 (5)
C15'—C14—C15—C16−47.2 (12)N2—C4—N4—C6156.5 (3)
O8—C14—C15—C1653.5 (10)N3—C12—N4—C497.1 (3)
O8—C14—C15'—C16'−63.6 (12)C13—C12—N4—C4−140.3 (2)
C15—C14—C15'—C16'29.3 (12)C7—C12—N4—C4−13.1 (3)
O3—C3—N1—C1−28.7 (4)N3—C12—N4—C6−42.3 (4)
N3—C3—N1—C1155.2 (3)C13—C12—N4—C680.3 (3)
O3—C3—N1—C7−165.5 (3)C7—C12—N4—C6−152.5 (3)
N3—C3—N1—C718.4 (3)O2—C6—N4—C4−82.6 (4)
O1—C1—N1—C3−83.7 (3)O2—C6—N4—C1252.7 (4)
O1—C1—N1—C751.1 (3)N1—C1—O1—C2−60.0 (3)
N2—C7—N1—C397.6 (3)N2—C2—O1—C160.1 (4)
C8—C7—N1—C3−137.4 (2)N3—C5—O2—C660.9 (4)
C12—C7—N1—C3−12.4 (3)N4—C6—O2—C5−61.5 (4)
N2—C7—N1—C1−40.6 (3)O5—C8—O6—C90.3 (4)
C8—C7—N1—C184.4 (3)C7—C8—O6—C9−178.1 (3)
C12—C7—N1—C1−150.7 (2)C10—C9—O6—C8169.5 (3)
O4—C4—N2—C225.2 (5)O7—C13—O8—C140.0 (5)
N4—C4—N2—C2−158.2 (3)C12—C13—O8—C14177.8 (3)
O4—C4—N2—C7165.8 (3)C15'—C14—O8—C13−155.8 (6)
N4—C4—N2—C7−17.6 (3)C15—C14—O8—C13163.3 (4)
O1—C2—N2—C487.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14A···O2i0.972.583.482 (5)155
C9—H9B···O4ii0.972.583.388 (4)141
C5—H5B···O7iii0.972.453.310 (4)148
C9—H9A···O1iv0.972.503.364 (4)149
C2—H2A···O3iv0.972.463.368 (4)155
C1—H1B···O7v0.972.553.231 (4)128

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+3/2, −y, z−1/2; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2262).

References

  • Branda, N., Grotzfeld, R. M., Valdes, C. & Rebek, J. (1995). J. Am. Chem. Soc.117, 85–88.
  • Bruker (2001). SMART (Version 5.628), SAINT (Version 6.45) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Elemans, J. A. A. W., Claase, M. B., Aarts, P. P. M., Rowan, A. E., Schenning, A. P. H. J. & Nolte, R. J. M. (1999). J. Org. Chem.64, 7009–7016.
  • Gao, M. & Sun, J.-J. (2007). Acta Cryst. E63, o3480.
  • Isaacs, L. & Witt, D. (2002). Angew. Chem. Int. Ed.41, 1905–1907. [PubMed]
  • Isaacs, L., Witt, D. & Fettinger, J. C. (1999). Chem. Commun. pp. 2549–2550.
  • Li, Y.-T., Li, J. & Wen, L.-L. (2007). Acta Cryst. E63, o287–o288.
  • Rebek, J. Jr (1999). Acc. Chem. Res.32, 278–286.
  • Rowan, A. E., Elemans, J. A. A. W. & Nolte, R. J. M. (1999). Acc. Chem. Res.32, 995–1006.
  • She, N.-F. & Xi, H.-L. (2007). Acta Cryst. E63, o3495.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Witt, D., Lagona, J., Damkaci, F., Fettinger, J. C. & Isaacs, L. (2000). Org. Lett.2, 755–758. [PubMed]
  • Wu, A., Chakraborty, A., Witt, D., Lagona, J., Damkaci, F., Ofori, M. A., Chiles, J. K., Fettinger, J. C. & Isaacs, L. (2002). J. Org. Chem.67, 5817–5830. [PubMed]

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