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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1100.
Published online 2009 April 25. doi:  10.1107/S1600536809014548
PMCID: PMC2977778

Diethyl 1,4-dioxo-1,2,2a,3,4,10b-hexahydro-5H,10H-2,3,4a,10a-tetraaza­benzo[g]cyclopenta[cd]azulene-2a,10b-dicarboxylate

Abstract

In the title compound, C18H20N4O6, the dihedral angle between the two fused five-membered rings in the glycoluril unit is 64.42 (2)°. The crystal structure features inter­molecular N—H(...)O and C—H(...)O interactions. An intramolecular C—H(...)O contact is also present.

Related literature

For the preparation of the title compound, see: Wu et al. (2002a [triangle]). For crystal engineering studies of glycoluril and its derivatives, see: Chen et al. (2007 [triangle]); Wang et al. (2006 [triangle]); Johnson et al. (2002 [triangle]); Wu et al. (2002b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1100-scheme1.jpg

Experimental

Crystal data

  • C18H20N4O6
  • M r = 388.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1100-efi1.jpg
  • a = 8.1394 (5) Å
  • b = 9.4425 (5) Å
  • c = 13.3576 (8) Å
  • α = 93.1550 (10)°
  • β = 96.0560 (10)°
  • γ = 112.3970 (10)°
  • V = 938.80 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 294 K
  • 0.20 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 [triangle]) T min = 0.976, T max = 0.989
  • 7700 measured reflections
  • 3624 independent reflections
  • 3028 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.144
  • S = 1.05
  • 3624 reflections
  • 261 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.20 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, 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 I, global. DOI: 10.1107/S1600536809014548/nc2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014548/nc2142Isup2.hkl

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

Acknowledgments

The author gratefully acknowledges support from Central China Normal University.

supplementary crystallographic information

Comment

Glycoluril and its derivatives have been widely studied in supramolecular chemistry (Johnson et al., 2002; Wu et al., 2002b). As a continuation of our recent studies in this area (Wang et al., 2006; Chen et al., 2007), we herein report the crystal structure of the title compound (Fig. 1). The dihedral angle between the two fused five-membered rings in the glycoluril unit is 64.42 (2) °. In the crystal structure the molecules are connected via weak intermolecular N—H···O hydrogen bonding (Table 1).

Experimental

The title compound was synthesized according to a literature procedure (Wu et al.; 2002a). Crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a dichloromethane-methanol (1:2) solution of the title compound at room temperature.

Refinement

All H atoms were positioned with idealized geometry with C—H = 0.93–0.97 Å (methyl H atoms allowed to rotate but not to tip) and were refined isotropic (Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) (methyl C)) using a riding model.

Figures

Fig. 1.
A view of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C18H20N4O6Z = 2
Mr = 388.38F(000) = 408
Triclinic, P1Dx = 1.374 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1394 (5) ÅCell parameters from 3262 reflections
b = 9.4425 (5) Åθ = 2.4–27.5°
c = 13.3576 (8) ŵ = 0.11 mm1
α = 93.155 (1)°T = 294 K
β = 96.056 (1)°Block, colorless
γ = 112.397 (1)°0.20 × 0.20 × 0.10 mm
V = 938.80 (9) Å3

Data collection

Bruker SMART 4K CCD area-detector diffractometer3624 independent reflections
Radiation source: fine-focus sealed tube3028 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] and ω scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)h = −10→8
Tmin = 0.976, Tmax = 0.989k = −11→11
7700 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0741P)2 + 0.3055P] where P = (Fo2 + 2Fc2)/3
3624 reflections(Δ/σ)max = 0.005
261 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.20 e Å3

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*/Ueq
C10.7535 (3)0.3332 (2)0.06082 (12)0.0350 (4)
C20.6905 (3)0.1940 (2)0.00001 (15)0.0442 (5)
H20.57140.1512−0.02980.053*
C30.8025 (3)0.1180 (2)−0.01692 (16)0.0516 (5)
H30.75890.0250−0.05790.062*
C40.9787 (3)0.1811 (2)0.02733 (16)0.0515 (5)
H41.05520.13180.01520.062*
C51.0421 (3)0.3177 (2)0.08982 (15)0.0437 (5)
H51.16070.35810.12070.052*
C60.9321 (2)0.3955 (2)0.10733 (12)0.0352 (4)
C70.6302 (3)0.4178 (2)0.07030 (12)0.0375 (4)
H7A0.67810.51300.03910.045*
H7B0.51410.35560.03210.045*
C81.0095 (2)0.5470 (2)0.17322 (13)0.0359 (4)
H8A1.13230.56660.20060.043*
H8B1.01230.62870.13160.043*
C90.4886 (3)0.3441 (2)0.22434 (14)0.0392 (4)
C100.9584 (3)0.5307 (2)0.35329 (13)0.0395 (4)
C110.7426 (2)0.5735 (2)0.24235 (12)0.0330 (4)
C120.7751 (3)0.7358 (2)0.20982 (13)0.0372 (4)
C130.9500 (4)1.0015 (3)0.2570 (2)0.0691 (7)
H13A1.04811.03060.21680.083*
H13B0.84941.01520.21950.083*
C141.0045 (7)1.0966 (3)0.3520 (3)0.1181 (14)
H14A0.90411.07290.38910.177*
H14B1.04691.20310.33980.177*
H14C1.09881.07740.39060.177*
C150.6771 (3)0.5423 (2)0.34897 (13)0.0379 (4)
C160.6154 (3)0.6578 (2)0.40178 (14)0.0412 (4)
C170.4679 (4)0.8288 (3)0.3831 (2)0.0741 (8)
H17A0.56090.90120.43350.089*
H17B0.36390.77560.41600.089*
C180.4201 (6)0.9114 (4)0.3022 (3)0.1120 (13)
H18A0.52520.96870.27270.168*
H18B0.37180.98080.33000.168*
H18C0.33210.83860.25110.168*
N10.6035 (2)0.45511 (17)0.17377 (10)0.0356 (4)
N20.9101 (2)0.55255 (17)0.25637 (10)0.0345 (4)
N30.5268 (3)0.3968 (2)0.32473 (13)0.0491 (4)
H3A0.456 (3)0.355 (3)0.3683 (19)0.059*
N40.8307 (3)0.5358 (2)0.40898 (13)0.0532 (5)
H4A0.835 (3)0.525 (3)0.472 (2)0.064*
O10.37312 (19)0.22369 (16)0.18597 (12)0.0528 (4)
O21.0959 (2)0.51339 (19)0.38374 (10)0.0531 (4)
O30.7018 (2)0.75960 (17)0.13482 (10)0.0552 (4)
O40.8984 (2)0.84003 (15)0.27670 (11)0.0526 (4)
O50.6376 (3)0.68292 (19)0.49151 (11)0.0644 (5)
O60.5323 (2)0.71765 (18)0.33836 (11)0.0556 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0430 (10)0.0384 (9)0.0271 (8)0.0191 (8)0.0058 (7)0.0050 (7)
C20.0461 (11)0.0437 (10)0.0410 (10)0.0161 (9)0.0054 (8)0.0024 (8)
C30.0708 (15)0.0391 (11)0.0507 (12)0.0266 (11)0.0138 (11)0.0024 (9)
C40.0657 (15)0.0492 (12)0.0557 (12)0.0368 (11)0.0181 (11)0.0113 (10)
C50.0426 (11)0.0528 (11)0.0450 (10)0.0261 (10)0.0106 (9)0.0166 (9)
C60.0391 (10)0.0427 (10)0.0286 (8)0.0197 (8)0.0072 (7)0.0108 (7)
C70.0406 (10)0.0476 (10)0.0266 (8)0.0221 (9)−0.0021 (7)−0.0009 (7)
C80.0340 (10)0.0443 (10)0.0305 (9)0.0155 (8)0.0059 (7)0.0078 (7)
C90.0373 (10)0.0384 (10)0.0451 (10)0.0186 (9)0.0059 (8)0.0022 (8)
C100.0412 (11)0.0464 (10)0.0293 (9)0.0160 (9)0.0003 (8)0.0062 (8)
C110.0354 (10)0.0382 (9)0.0262 (8)0.0151 (8)0.0042 (7)0.0044 (7)
C120.0419 (10)0.0411 (10)0.0312 (9)0.0186 (9)0.0061 (8)0.0055 (7)
C130.0793 (18)0.0386 (12)0.0763 (17)0.0093 (12)0.0038 (14)0.0123 (11)
C140.170 (4)0.0489 (16)0.107 (3)0.019 (2)0.001 (3)−0.0135 (16)
C150.0405 (10)0.0436 (10)0.0296 (9)0.0160 (9)0.0055 (7)0.0056 (7)
C160.0412 (11)0.0415 (10)0.0350 (10)0.0092 (9)0.0087 (8)−0.0008 (8)
C170.0743 (18)0.0650 (16)0.096 (2)0.0388 (15)0.0268 (15)−0.0014 (14)
C180.123 (3)0.088 (2)0.143 (3)0.070 (2)−0.014 (3)0.001 (2)
N10.0346 (8)0.0415 (8)0.0296 (7)0.0153 (7)0.0002 (6)0.0005 (6)
N20.0339 (8)0.0433 (8)0.0263 (7)0.0155 (7)0.0013 (6)0.0051 (6)
N30.0571 (11)0.0412 (9)0.0423 (9)0.0088 (8)0.0185 (8)0.0041 (7)
N40.0579 (12)0.0867 (14)0.0265 (8)0.0393 (11)0.0068 (8)0.0152 (8)
O10.0427 (8)0.0437 (8)0.0624 (9)0.0079 (7)0.0054 (7)−0.0045 (7)
O20.0493 (9)0.0791 (11)0.0373 (7)0.0323 (8)0.0003 (6)0.0148 (7)
O30.0773 (11)0.0517 (9)0.0407 (8)0.0328 (8)−0.0054 (7)0.0069 (6)
O40.0588 (9)0.0372 (7)0.0505 (8)0.0091 (7)−0.0048 (7)0.0069 (6)
O50.0891 (13)0.0677 (10)0.0367 (8)0.0307 (9)0.0136 (8)−0.0042 (7)
O60.0633 (10)0.0630 (9)0.0520 (9)0.0378 (8)0.0095 (7)0.0002 (7)

Geometric parameters (Å, °)

C1—C21.390 (3)C11—C121.548 (2)
C1—C61.401 (3)C11—C151.577 (2)
C1—C71.513 (2)C12—O31.188 (2)
C2—C31.386 (3)C12—O41.317 (2)
C2—H20.9300C13—C141.437 (4)
C3—C41.375 (3)C13—O41.466 (3)
C3—H30.9300C13—H13A0.9700
C4—C51.382 (3)C13—H13B0.9700
C4—H40.9300C14—H14A0.9600
C5—C61.387 (3)C14—H14B0.9600
C5—H50.9300C14—H14C0.9600
C6—C81.508 (3)C15—N41.437 (2)
C7—N11.466 (2)C15—N31.441 (3)
C7—H7A0.9700C15—C161.531 (3)
C7—H7B0.9700C16—O51.190 (2)
C8—N21.451 (2)C16—O61.311 (2)
C8—H8A0.9700C17—O61.466 (3)
C8—H8B0.9700C17—C181.471 (4)
C9—O11.208 (2)C17—H17A0.9700
C9—N31.365 (3)C17—H17B0.9700
C9—N11.376 (2)C18—H18A0.9600
C10—O21.223 (2)C18—H18B0.9600
C10—N41.354 (3)C18—H18C0.9600
C10—N21.363 (2)N3—H3A0.87 (3)
C11—N11.440 (2)N4—H4A0.85 (3)
C11—N21.445 (2)
C2—C1—C6119.23 (17)C14—C13—H13A109.9
C2—C1—C7119.00 (17)O4—C13—H13A109.9
C6—C1—C7121.69 (16)C14—C13—H13B109.9
C3—C2—C1121.0 (2)O4—C13—H13B109.9
C3—C2—H2119.5H13A—C13—H13B108.3
C1—C2—H2119.5C13—C14—H14A109.5
C4—C3—C2119.5 (2)C13—C14—H14B109.5
C4—C3—H3120.3H14A—C14—H14B109.5
C2—C3—H3120.3C13—C14—H14C109.5
C3—C4—C5120.1 (2)H14A—C14—H14C109.5
C3—C4—H4120.0H14B—C14—H14C109.5
C5—C4—H4120.0N4—C15—N3114.94 (17)
C4—C5—C6121.16 (19)N4—C15—C16110.13 (16)
C4—C5—H5119.4N3—C15—C16109.09 (16)
C6—C5—H5119.4N4—C15—C11102.62 (15)
C5—C6—C1118.94 (18)N3—C15—C11101.34 (14)
C5—C6—C8119.12 (17)C16—C15—C11118.67 (15)
C1—C6—C8121.91 (16)O5—C16—O6125.5 (2)
N1—C7—C1115.68 (14)O5—C16—C15121.54 (18)
N1—C7—H7A108.4O6—C16—C15112.92 (15)
C1—C7—H7A108.4O6—C17—C18108.6 (3)
N1—C7—H7B108.4O6—C17—H17A110.0
C1—C7—H7B108.4C18—C17—H17A110.0
H7A—C7—H7B107.4O6—C17—H17B110.0
N2—C8—C6113.76 (15)C18—C17—H17B110.0
N2—C8—H8A108.8H17A—C17—H17B108.3
C6—C8—H8A108.8C17—C18—H18A109.5
N2—C8—H8B108.8C17—C18—H18B109.5
C6—C8—H8B108.8H18A—C18—H18B109.5
H8A—C8—H8B107.7C17—C18—H18C109.5
O1—C9—N3126.68 (18)H18A—C18—H18C109.5
O1—C9—N1125.85 (18)H18B—C18—H18C109.5
N3—C9—N1107.45 (16)C9—N1—C11111.93 (14)
O2—C10—N4126.78 (16)C9—N1—C7120.52 (15)
O2—C10—N2125.11 (18)C11—N1—C7121.64 (15)
N4—C10—N2108.09 (16)C10—N2—C11113.25 (15)
N1—C11—N2113.91 (14)C10—N2—C8124.21 (15)
N1—C11—C12111.49 (13)C11—N2—C8122.46 (13)
N2—C11—C12109.92 (14)C9—N3—C15114.32 (16)
N1—C11—C15103.63 (14)C9—N3—H3A122.6 (16)
N2—C11—C15101.80 (13)C15—N3—H3A122.3 (16)
C12—C11—C15115.76 (14)C10—N4—C15113.12 (15)
O3—C12—O4126.43 (17)C10—N4—H4A123.5 (17)
O3—C12—C11124.36 (17)C15—N4—H4A123.0 (17)
O4—C12—C11109.19 (14)C12—O4—C13116.92 (16)
C14—C13—O4108.9 (2)C16—O6—C17116.28 (18)
C6—C1—C2—C3−1.4 (3)O1—C9—N1—C7−17.8 (3)
C7—C1—C2—C3175.22 (17)N3—C9—N1—C7163.56 (16)
C1—C2—C3—C40.2 (3)N2—C11—N1—C997.72 (17)
C2—C3—C4—C51.3 (3)C12—C11—N1—C9−137.17 (15)
C3—C4—C5—C6−1.5 (3)C15—C11—N1—C9−12.01 (18)
C4—C5—C6—C10.3 (3)N2—C11—N1—C7−55.3 (2)
C4—C5—C6—C8−177.86 (17)C12—C11—N1—C769.8 (2)
C2—C1—C6—C51.2 (2)C15—C11—N1—C7−165.00 (14)
C7—C1—C6—C5−175.36 (16)C1—C7—N1—C9−78.3 (2)
C2—C1—C6—C8179.26 (16)C1—C7—N1—C1172.4 (2)
C7—C1—C6—C82.7 (2)O2—C10—N2—C11−178.59 (18)
C2—C1—C7—N1124.69 (18)N4—C10—N2—C11−0.2 (2)
C6—C1—C7—N1−58.8 (2)O2—C10—N2—C84.8 (3)
C5—C6—C8—N2−126.25 (17)N4—C10—N2—C8−176.82 (17)
C1—C6—C8—N255.7 (2)N1—C11—N2—C10−116.92 (17)
N1—C11—C12—O3−3.8 (3)C12—C11—N2—C10117.15 (16)
N2—C11—C12—O3123.5 (2)C15—C11—N2—C10−6.07 (19)
C15—C11—C12—O3−121.9 (2)N1—C11—N2—C859.8 (2)
N1—C11—C12—O4177.71 (15)C12—C11—N2—C8−66.1 (2)
N2—C11—C12—O4−55.00 (19)C15—C11—N2—C8170.64 (15)
C15—C11—C12—O459.6 (2)C6—C8—N2—C1099.2 (2)
N1—C11—C15—N4127.94 (15)C6—C8—N2—C11−77.2 (2)
N2—C11—C15—N49.48 (18)O1—C9—N3—C15177.73 (18)
C12—C11—C15—N4−109.69 (17)N1—C9—N3—C15−3.7 (2)
N1—C11—C15—N38.88 (17)N4—C15—N3—C9−113.33 (19)
N2—C11—C15—N3−109.58 (15)C16—C15—N3—C9122.44 (18)
C12—C11—C15—N3131.26 (16)C11—C15—N3—C9−3.5 (2)
N1—C11—C15—C16−110.44 (17)O2—C10—N4—C15−174.2 (2)
N2—C11—C15—C16131.09 (17)N2—C10—N4—C157.4 (2)
C12—C11—C15—C1611.9 (2)N3—C15—N4—C1098.4 (2)
N4—C15—C16—O5−29.5 (3)C16—C15—N4—C10−137.96 (18)
N3—C15—C16—O597.5 (2)C11—C15—N4—C10−10.7 (2)
C11—C15—C16—O5−147.25 (19)O3—C12—O4—C130.2 (3)
N4—C15—C16—O6153.07 (17)C11—C12—O4—C13178.62 (19)
N3—C15—C16—O6−79.91 (19)C14—C13—O4—C12150.2 (3)
C11—C15—C16—O635.3 (2)O5—C16—O6—C172.3 (3)
O1—C9—N1—C11−171.16 (18)C15—C16—O6—C17179.63 (19)
N3—C9—N1—C1110.2 (2)C18—C17—O6—C16166.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7A···O30.972.523.107 (2)119
C17—H17B···O2i0.972.583.343 (3)136
C7—H7B···O3ii0.972.593.478 (2)153
N4—H4A···O2iii0.85 (3)2.05 (3)2.871 (2)165 (2)
N3—H3A···O5iv0.87 (3)2.09 (3)2.917 (2)159 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2142).

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