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

In the title compound, C(18)H(20)N(4)O(6), the dihedral angle between the two fused five-membered rings in the glycoluril unit is 64.42 (2)°. The crystal structure features inter-molecular 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 ▶). For crystal engineering studies of glycoluril and its derivatives, see: Chen et al. (2007 ▶); Wang et al. (2006 ▶); Johnson et al. (2002 ▶); Wu et al. (2002b ▶).

Experimental

Crystal data

C18H20N4O6

M = 388.38

Triclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

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

C18H20N4O6	Z = 2
Mr = 388.38	F(000) = 408
Triclinic, P1	Dx = 1.374 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1394 (5) Å	Cell parameters from 3262 reflections
b = 9.4425 (5) Å	θ = 2.4–27.5°
c = 13.3576 (8) Å	µ = 0.11 mm−1
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

Bruker SMART 4K CCD area-detector diffractometer	3624 independent reflections
Radiation source: fine-focus sealed tube	3028 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −10→8
Tmin = 0.976, Tmax = 0.989	k = −11→11
7700 measured reflections	l = −16→16

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

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.

	x	y	z	Uiso*/Ueq
C1	0.7535 (3)	0.3332 (2)	0.06082 (12)	0.0350 (4)
C2	0.6905 (3)	0.1940 (2)	0.00001 (15)	0.0442 (5)
H2	0.5714	0.1512	−0.0298	0.053*
C3	0.8025 (3)	0.1180 (2)	−0.01692 (16)	0.0516 (5)
H3	0.7589	0.0250	−0.0579	0.062*
C4	0.9787 (3)	0.1811 (2)	0.02733 (16)	0.0515 (5)
H4	1.0552	0.1318	0.0152	0.062*
C5	1.0421 (3)	0.3177 (2)	0.08982 (15)	0.0437 (5)
H5	1.1607	0.3581	0.1207	0.052*
C6	0.9321 (2)	0.3955 (2)	0.10733 (12)	0.0352 (4)
C7	0.6302 (3)	0.4178 (2)	0.07030 (12)	0.0375 (4)
H7A	0.6781	0.5130	0.0391	0.045*
H7B	0.5141	0.3556	0.0321	0.045*
C8	1.0095 (2)	0.5470 (2)	0.17322 (13)	0.0359 (4)
H8A	1.1323	0.5666	0.2006	0.043*
H8B	1.0123	0.6287	0.1316	0.043*
C9	0.4886 (3)	0.3441 (2)	0.22434 (14)	0.0392 (4)
C10	0.9584 (3)	0.5307 (2)	0.35329 (13)	0.0395 (4)
C11	0.7426 (2)	0.5735 (2)	0.24235 (12)	0.0330 (4)
C12	0.7751 (3)	0.7358 (2)	0.20982 (13)	0.0372 (4)
C13	0.9500 (4)	1.0015 (3)	0.2570 (2)	0.0691 (7)
H13A	1.0481	1.0306	0.2168	0.083*
H13B	0.8494	1.0152	0.2195	0.083*
C14	1.0045 (7)	1.0966 (3)	0.3520 (3)	0.1181 (14)
H14A	0.9041	1.0729	0.3891	0.177*
H14B	1.0469	1.2031	0.3398	0.177*
H14C	1.0988	1.0774	0.3906	0.177*
C15	0.6771 (3)	0.5423 (2)	0.34897 (13)	0.0379 (4)
C16	0.6154 (3)	0.6578 (2)	0.40178 (14)	0.0412 (4)
C17	0.4679 (4)	0.8288 (3)	0.3831 (2)	0.0741 (8)
H17A	0.5609	0.9012	0.4335	0.089*
H17B	0.3639	0.7756	0.4160	0.089*
C18	0.4201 (6)	0.9114 (4)	0.3022 (3)	0.1120 (13)
H18A	0.5252	0.9687	0.2727	0.168*
H18B	0.3718	0.9808	0.3300	0.168*
H18C	0.3321	0.8386	0.2511	0.168*
N1	0.6035 (2)	0.45511 (17)	0.17377 (10)	0.0356 (4)
N2	0.9101 (2)	0.55255 (17)	0.25637 (10)	0.0345 (4)
N3	0.5268 (3)	0.3968 (2)	0.32473 (13)	0.0491 (4)
H3A	0.456 (3)	0.355 (3)	0.3683 (19)	0.059*
N4	0.8307 (3)	0.5358 (2)	0.40898 (13)	0.0532 (5)
H4A	0.835 (3)	0.525 (3)	0.472 (2)	0.064*
O1	0.37312 (19)	0.22369 (16)	0.18597 (12)	0.0528 (4)
O2	1.0959 (2)	0.51339 (19)	0.38374 (10)	0.0531 (4)
O3	0.7018 (2)	0.75960 (17)	0.13482 (10)	0.0552 (4)
O4	0.8984 (2)	0.84003 (15)	0.27670 (11)	0.0526 (4)
O5	0.6376 (3)	0.68292 (19)	0.49151 (11)	0.0644 (5)
O6	0.5323 (2)	0.71765 (18)	0.33836 (11)	0.0556 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0430 (10)	0.0384 (9)	0.0271 (8)	0.0191 (8)	0.0058 (7)	0.0050 (7)
C2	0.0461 (11)	0.0437 (10)	0.0410 (10)	0.0161 (9)	0.0054 (8)	0.0024 (8)
C3	0.0708 (15)	0.0391 (11)	0.0507 (12)	0.0266 (11)	0.0138 (11)	0.0024 (9)
C4	0.0657 (15)	0.0492 (12)	0.0557 (12)	0.0368 (11)	0.0181 (11)	0.0113 (10)
C5	0.0426 (11)	0.0528 (11)	0.0450 (10)	0.0261 (10)	0.0106 (9)	0.0166 (9)
C6	0.0391 (10)	0.0427 (10)	0.0286 (8)	0.0197 (8)	0.0072 (7)	0.0108 (7)
C7	0.0406 (10)	0.0476 (10)	0.0266 (8)	0.0221 (9)	−0.0021 (7)	−0.0009 (7)
C8	0.0340 (10)	0.0443 (10)	0.0305 (9)	0.0155 (8)	0.0059 (7)	0.0078 (7)
C9	0.0373 (10)	0.0384 (10)	0.0451 (10)	0.0186 (9)	0.0059 (8)	0.0022 (8)
C10	0.0412 (11)	0.0464 (10)	0.0293 (9)	0.0160 (9)	0.0003 (8)	0.0062 (8)
C11	0.0354 (10)	0.0382 (9)	0.0262 (8)	0.0151 (8)	0.0042 (7)	0.0044 (7)
C12	0.0419 (10)	0.0411 (10)	0.0312 (9)	0.0186 (9)	0.0061 (8)	0.0055 (7)
C13	0.0793 (18)	0.0386 (12)	0.0763 (17)	0.0093 (12)	0.0038 (14)	0.0123 (11)
C14	0.170 (4)	0.0489 (16)	0.107 (3)	0.019 (2)	0.001 (3)	−0.0135 (16)
C15	0.0405 (10)	0.0436 (10)	0.0296 (9)	0.0160 (9)	0.0055 (7)	0.0056 (7)
C16	0.0412 (11)	0.0415 (10)	0.0350 (10)	0.0092 (9)	0.0087 (8)	−0.0008 (8)
C17	0.0743 (18)	0.0650 (16)	0.096 (2)	0.0388 (15)	0.0268 (15)	−0.0014 (14)
C18	0.123 (3)	0.088 (2)	0.143 (3)	0.070 (2)	−0.014 (3)	0.001 (2)
N1	0.0346 (8)	0.0415 (8)	0.0296 (7)	0.0153 (7)	0.0002 (6)	0.0005 (6)
N2	0.0339 (8)	0.0433 (8)	0.0263 (7)	0.0155 (7)	0.0013 (6)	0.0051 (6)
N3	0.0571 (11)	0.0412 (9)	0.0423 (9)	0.0088 (8)	0.0185 (8)	0.0041 (7)
N4	0.0579 (12)	0.0867 (14)	0.0265 (8)	0.0393 (11)	0.0068 (8)	0.0152 (8)
O1	0.0427 (8)	0.0437 (8)	0.0624 (9)	0.0079 (7)	0.0054 (7)	−0.0045 (7)
O2	0.0493 (9)	0.0791 (11)	0.0373 (7)	0.0323 (8)	0.0003 (6)	0.0148 (7)
O3	0.0773 (11)	0.0517 (9)	0.0407 (8)	0.0328 (8)	−0.0054 (7)	0.0069 (6)
O4	0.0588 (9)	0.0372 (7)	0.0505 (8)	0.0091 (7)	−0.0048 (7)	0.0069 (6)
O5	0.0891 (13)	0.0677 (10)	0.0367 (8)	0.0307 (9)	0.0136 (8)	−0.0042 (7)
O6	0.0633 (10)	0.0630 (9)	0.0520 (9)	0.0378 (8)	0.0095 (7)	0.0002 (7)

C1—C2	1.390 (3)	C11—C12	1.548 (2)
C1—C6	1.401 (3)	C11—C15	1.577 (2)
C1—C7	1.513 (2)	C12—O3	1.188 (2)
C2—C3	1.386 (3)	C12—O4	1.317 (2)
C2—H2	0.9300	C13—C14	1.437 (4)
C3—C4	1.375 (3)	C13—O4	1.466 (3)
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.382 (3)	C13—H13B	0.9700
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.387 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—C8	1.508 (3)	C15—N4	1.437 (2)
C7—N1	1.466 (2)	C15—N3	1.441 (3)
C7—H7A	0.9700	C15—C16	1.531 (3)
C7—H7B	0.9700	C16—O5	1.190 (2)
C8—N2	1.451 (2)	C16—O6	1.311 (2)
C8—H8A	0.9700	C17—O6	1.466 (3)
C8—H8B	0.9700	C17—C18	1.471 (4)
C9—O1	1.208 (2)	C17—H17A	0.9700
C9—N3	1.365 (3)	C17—H17B	0.9700
C9—N1	1.376 (2)	C18—H18A	0.9600
C10—O2	1.223 (2)	C18—H18B	0.9600
C10—N4	1.354 (3)	C18—H18C	0.9600
C10—N2	1.363 (2)	N3—H3A	0.87 (3)
C11—N1	1.440 (2)	N4—H4A	0.85 (3)
C11—N2	1.445 (2)
C2—C1—C6	119.23 (17)	C14—C13—H13A	109.9
C2—C1—C7	119.00 (17)	O4—C13—H13A	109.9
C6—C1—C7	121.69 (16)	C14—C13—H13B	109.9
C3—C2—C1	121.0 (2)	O4—C13—H13B	109.9
C3—C2—H2	119.5	H13A—C13—H13B	108.3
C1—C2—H2	119.5	C13—C14—H14A	109.5
C4—C3—C2	119.5 (2)	C13—C14—H14B	109.5
C4—C3—H3	120.3	H14A—C14—H14B	109.5
C2—C3—H3	120.3	C13—C14—H14C	109.5
C3—C4—C5	120.1 (2)	H14A—C14—H14C	109.5
C3—C4—H4	120.0	H14B—C14—H14C	109.5
C5—C4—H4	120.0	N4—C15—N3	114.94 (17)
C4—C5—C6	121.16 (19)	N4—C15—C16	110.13 (16)
C4—C5—H5	119.4	N3—C15—C16	109.09 (16)
C6—C5—H5	119.4	N4—C15—C11	102.62 (15)
C5—C6—C1	118.94 (18)	N3—C15—C11	101.34 (14)
C5—C6—C8	119.12 (17)	C16—C15—C11	118.67 (15)
C1—C6—C8	121.91 (16)	O5—C16—O6	125.5 (2)
N1—C7—C1	115.68 (14)	O5—C16—C15	121.54 (18)
N1—C7—H7A	108.4	O6—C16—C15	112.92 (15)
C1—C7—H7A	108.4	O6—C17—C18	108.6 (3)
N1—C7—H7B	108.4	O6—C17—H17A	110.0
C1—C7—H7B	108.4	C18—C17—H17A	110.0
H7A—C7—H7B	107.4	O6—C17—H17B	110.0
N2—C8—C6	113.76 (15)	C18—C17—H17B	110.0
N2—C8—H8A	108.8	H17A—C17—H17B	108.3
C6—C8—H8A	108.8	C17—C18—H18A	109.5
N2—C8—H8B	108.8	C17—C18—H18B	109.5
C6—C8—H8B	108.8	H18A—C18—H18B	109.5
H8A—C8—H8B	107.7	C17—C18—H18C	109.5
O1—C9—N3	126.68 (18)	H18A—C18—H18C	109.5
O1—C9—N1	125.85 (18)	H18B—C18—H18C	109.5
N3—C9—N1	107.45 (16)	C9—N1—C11	111.93 (14)
O2—C10—N4	126.78 (16)	C9—N1—C7	120.52 (15)
O2—C10—N2	125.11 (18)	C11—N1—C7	121.64 (15)
N4—C10—N2	108.09 (16)	C10—N2—C11	113.25 (15)
N1—C11—N2	113.91 (14)	C10—N2—C8	124.21 (15)
N1—C11—C12	111.49 (13)	C11—N2—C8	122.46 (13)
N2—C11—C12	109.92 (14)	C9—N3—C15	114.32 (16)
N1—C11—C15	103.63 (14)	C9—N3—H3A	122.6 (16)
N2—C11—C15	101.80 (13)	C15—N3—H3A	122.3 (16)
C12—C11—C15	115.76 (14)	C10—N4—C15	113.12 (15)
O3—C12—O4	126.43 (17)	C10—N4—H4A	123.5 (17)
O3—C12—C11	124.36 (17)	C15—N4—H4A	123.0 (17)
O4—C12—C11	109.19 (14)	C12—O4—C13	116.92 (16)
C14—C13—O4	108.9 (2)	C16—O6—C17	116.28 (18)
C6—C1—C2—C3	−1.4 (3)	O1—C9—N1—C7	−17.8 (3)
C7—C1—C2—C3	175.22 (17)	N3—C9—N1—C7	163.56 (16)
C1—C2—C3—C4	0.2 (3)	N2—C11—N1—C9	97.72 (17)
C2—C3—C4—C5	1.3 (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—C1	0.3 (3)	N2—C11—N1—C7	−55.3 (2)
C4—C5—C6—C8	−177.86 (17)	C12—C11—N1—C7	69.8 (2)
C2—C1—C6—C5	1.2 (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—C8	179.26 (16)	C1—C7—N1—C11	72.4 (2)
C7—C1—C6—C8	2.7 (2)	O2—C10—N2—C11	−178.59 (18)
C2—C1—C7—N1	124.69 (18)	N4—C10—N2—C11	−0.2 (2)
C6—C1—C7—N1	−58.8 (2)	O2—C10—N2—C8	4.8 (3)
C5—C6—C8—N2	−126.25 (17)	N4—C10—N2—C8	−176.82 (17)
C1—C6—C8—N2	55.7 (2)	N1—C11—N2—C10	−116.92 (17)
N1—C11—C12—O3	−3.8 (3)	C12—C11—N2—C10	117.15 (16)
N2—C11—C12—O3	123.5 (2)	C15—C11—N2—C10	−6.07 (19)
C15—C11—C12—O3	−121.9 (2)	N1—C11—N2—C8	59.8 (2)
N1—C11—C12—O4	177.71 (15)	C12—C11—N2—C8	−66.1 (2)
N2—C11—C12—O4	−55.00 (19)	C15—C11—N2—C8	170.64 (15)
C15—C11—C12—O4	59.6 (2)	C6—C8—N2—C10	99.2 (2)
N1—C11—C15—N4	127.94 (15)	C6—C8—N2—C11	−77.2 (2)
N2—C11—C15—N4	9.48 (18)	O1—C9—N3—C15	177.73 (18)
C12—C11—C15—N4	−109.69 (17)	N1—C9—N3—C15	−3.7 (2)
N1—C11—C15—N3	8.88 (17)	N4—C15—N3—C9	−113.33 (19)
N2—C11—C15—N3	−109.58 (15)	C16—C15—N3—C9	122.44 (18)
C12—C11—C15—N3	131.26 (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—C16	131.09 (17)	N2—C10—N4—C15	7.4 (2)
C12—C11—C15—C16	11.9 (2)	N3—C15—N4—C10	98.4 (2)
N4—C15—C16—O5	−29.5 (3)	C16—C15—N4—C10	−137.96 (18)
N3—C15—C16—O5	97.5 (2)	C11—C15—N4—C10	−10.7 (2)
C11—C15—C16—O5	−147.25 (19)	O3—C12—O4—C13	0.2 (3)
N4—C15—C16—O6	153.07 (17)	C11—C12—O4—C13	178.62 (19)
N3—C15—C16—O6	−79.91 (19)	C14—C13—O4—C12	150.2 (3)
C11—C15—C16—O6	35.3 (2)	O5—C16—O6—C17	2.3 (3)
O1—C9—N1—C11	−171.16 (18)	C15—C16—O6—C17	179.63 (19)
N3—C9—N1—C11	10.2 (2)	C18—C17—O6—C16	166.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O3	0.97	2.52	3.107 (2)	119
C17—H17B···O2i	0.97	2.58	3.343 (3)	136
C7—H7B···O3ii	0.97	2.59	3.478 (2)	153
N4—H4A···O2iii	0.85 (3)	2.05 (3)	2.871 (2)	165 (2)
N3—H3A···O5iv	0.87 (3)	2.09 (3)	2.917 (2)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O3	0.97	2.52	3.107 (2)	119
C17—H17B⋯O2i	0.97	2.58	3.343 (3)	136
C7—H7B⋯O3ii	0.97	2.59	3.478 (2)	153
N4—H4A⋯O2iii	0.85 (3)	2.05 (3)	2.871 (2)	165 (2)
N3—H3A⋯O5iv	0.87 (3)	2.09 (3)	2.917 (2)	159 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .