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

Qin, J.

doi:10.1107/S1600536809014548

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1100

doi:10.1107/S1600536809014548

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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

Jing Qin ^a ^*

^aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: qj0312@mails.ccnu.edu.cn

(Received 15 April 2009; accepted 19 April 2009; online 25 April 2009)

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 ). 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_r = 388.38
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.144
S = 1.05
3624 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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⋯O5^iv	0.87 (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.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014548/nc2142sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

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

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 top

Crystal data top

C₁₈H₂₀N₄O₆	Z = 2
M_r = 388.38	F(000) = 408
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0741P)² + 0.3055P] where P = (F_o² + 2F_c²)/3
3624 reflections	(Δ/σ)_max = 0.005
261 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₂₀N₄O₆	γ = 112.397 (1)°
M_r = 388.38	V = 938.80 (9) Å³
Triclinic, P1	Z = 2
a = 8.1394 (5) Å	Mo Kα radiation
b = 9.4425 (5) Å	µ = 0.11 mm⁻¹
c = 13.3576 (8) Å	T = 294 K
α = 93.155 (1)°	0.20 × 0.20 × 0.10 mm
β = 96.056 (1)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3624 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3028 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.989	R_int = 0.020
7700 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.28 e Å⁻³
3624 reflections	Δρ_min = −0.20 e Å⁻³
261 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O5^iv	0.87 (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.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₄O₆
M_r	388.38
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.1394 (5), 9.4425 (5), 13.3576 (8)
α, β, γ (°)	93.155 (1), 96.056 (1), 112.397 (1)
V (Å³)	938.80 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.976, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	7700, 3624, 3028
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.144, 1.05
No. of reflections	3624
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O3	0.97	2.52	3.107 (2)	118.6
C17—H17B···O2ⁱ	0.97	2.58	3.343 (3)	135.9
C7—H7B···O3ⁱⁱ	0.97	2.59	3.478 (2)	152.8
N4—H4A···O2ⁱⁱⁱ	0.85 (3)	2.05 (3)	2.871 (2)	165 (2)
N3—H3A···O5^iv	0.87 (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.

Acknowledgements

The author gratefully acknowledges support from Central China Normal University.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Y., She, N., Meng, X., Yin, G., Wu, A. & Isaacs, L. (2007). Org. Lett. 9, 1899–1902. Web of Science CrossRef PubMed CAS Google Scholar
Johnson, D. W., Palmer, L. C., Hof, F., Iovine, P. M. & Rebek, J. Jr (2002). Chem. Commun. pp. 2228–2229. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z., Zhou, B., Chen, Y., Yin, G., Li, Y., Wu, A. & Isaacs, L. (2006). J. Org. Chem. 71, 4502–4508. Web of Science CSD CrossRef PubMed CAS Google Scholar
Wu, A., Chakraborty, A., Witt, D., Lagona, J., Damkaci, F., Ofori, M. A., Chiles, J. K., Fettinger, J. C. & Isaacs, L. (2002a). J. Org. Chem. 67, 5817–5830. Web of Science CSD CrossRef PubMed CAS Google Scholar
Wu, A., Fettinger, J. C. & Isaacs, L. (2002b). Tetrahedron, 58, 9769–9777. Web of Science CSD CrossRef CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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