Diethyl 6,13-dioxo-5,7,12,13b,13c,14-hexa­hydro-6H,13H-5a,6a,12a,13a-tetra­azabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-13b,13c-dicarboxyl­ate 1,2-dichloro­ethane solvate

Liu, H.-X.; Wang, Z.-G.

doi:10.1107/S1600536809041373

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2746-o2747

https://doi.org/10.1107/S1600536809041373

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Diethyl 6,13-dioxo-5,7,12,13b,13c,14-hexahydro-6H,13H-5a,6a,12a,13a-tetraazabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-13b,13c-dicarboxylate 1,2-dichloroethane solvate

Hong-Xia Liu ^a and Zhi-Guo Wang ^b ^*

^aSchool of Environmental Science and Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China, and ^bSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: chwangzg@hsit.edu.cn

(Received 4 October 2009; accepted 10 October 2009; online 17 October 2009)

In the title inclusion compound, C₂₆H₂₆N₄O₆·C₂H₄Cl₂, the solvent molecule occupies a cavity inside the clip-type molecule which is based on the glycoluril skeleton with two ethyl acetate substituents on the convex face of the glycoluril system. The dihedral angle between the aromatic rings of the host is 43.59 (4)° and the centroid–centroid distance is 6.741 (5) Å. The 1,2-dichloroetane molecule adopts a gauche conformation enabling it to participate in C—H⋯π interactions with the host. The packing motif in the title compound differs from that observed in the crystal structures of the host and in the benzene solvate. The host molecules are linked into tapes by π–π stacking interactions (centroid–centroid distance = 3.733 Å) and are further assembled into layers via C—H⋯O interactions. One of the ethyl groups is disorded over two positions with site-occupancy factors of 0.702 (14) and 0.298 (14).

Related literature

For the related structures, see: Chen et al. (2007 ); Hof et al.,(2002 ); Hu et al. (2007 ); Isaacs & Fettinger (1999 ); Wang et al. (2006 ).

Experimental

Crystal data

C₂₆H₂₆N₄O₆·C₂H₄Cl₂
M_r = 589.46
Triclinic, $[P \overline 1]$
a = 8.9468 (10) Å
b = 11.1544 (13) Å
c = 15.6260 (18) Å
α = 69.257 (2)°
β = 82.688 (2)°
γ = 76.892 (2)°
V = 1418.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 292 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
10171 measured reflections
4947 independent reflections
4056 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.188
S = 1.04
4947 reflections
383 parameters
28 restraints
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28B⋯Cg2	0.97	2.55	3.476 (3)	160
C5—H5⋯O5ⁱ	0.93	2.59	3.393 (4)	145
C7—H7B⋯O5ⁱ	0.97	2.50	3.359 (3)	148
C14—H14A⋯O2ⁱⁱ	0.96	2.57	3.514 (9)	168
C14′—H14F⋯O2ⁱⁱ	0.96	2.47	3.351 (6)	153
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z+1. Cg2 is the centroid of the C21–C26 ring.

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: https://doi.org/10.1107/S1600536809041373/gk2232sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041373/gk2232Isup2.hkl

checkCIF report

Comment top

Molecular clips based on the glycoluril skeleton, which have a well defined geometry due to the rigidity of the fused rings, have been prepared for a wide variety of supramolecular applications, including molecular recognition (Hu et al., 2007), molecular assemblies (Hof et al., 2002), crystal engineering (Wang et al., 2006; Chen et al., 2007),

The title host compound is a kind of molecular receptor, possessing a well defined U-shaped cavity formed by the glycoluril framework with two aromatic side walls. The crystal structures of monoclinic apohost obtained from dichloroethane solution (C2/c, Z' = 1/2; Wang et al., 2006) and monoclinic benzene solvate, C₂₆H₂₆N₄O₆.0.25C₆H₆, (P2₁/c, Z' = 2; Isaacs et al., 1999) have been already reported. Here, we report the structure of a new solvate (P-1, Z' = 1), C₂₆H₂₆N₄O₆.C₂H₄Cl₂, crystallized from 1,2-dichoroethane/methanol (3:1 vol.) solution.

In the triclinic pseudopolymorph, the asymmetric unit contains one host molecule and one solvent molecule of 1,2-dichloroethane (Fig.1). There is a C-H···π interaction betweeen the host and the guest. The distance between atom H28B and Cg2 (the centroid of the C21—C26 ring) is 2.67 Å (Table 1).

As solvent molecule occupies the cavity, the title compound exhibits different packing motif than the previously known two monoclinic forms. In Isaacs structure, the molecule was kined into three-dimensional network structure by π-π stacking, C—H···π and C—H···O hydrogen-bonds. In our previously reported structure of the apohost, the ethyl group occupied the cavity with C—H···π interactions and the molecules were linked into layers to the ab plane by four pairs of C—H···O hydrogen-bonds parallel .

The title molecules are linked into tapes by π-π stacking interactions. The benzene rings Cg1 (C1—C6) in the molecules at (x, y, z) and (1 - x, 1 - y, 1 - z) are strictly parallel, with an interplanar spacing of 3.589 Å, a ring centroid separation of 3.733 Å and a centroid offset of 1.027 Å. In addition, intermolecular C—H···O (Table 1) hydrogen-bonds link molecules into two-dimensional layer structure.

Related literature top

For the related structures, see: Chen et al. (2007); Hof et al.,(2002); Hu et al. (2007); Isaacs & Fettinger (1999); Wang et al. (2006). Cg2 is the centroid of the C21–C26 ring.

Experimental top

The host compound was synthesized as reported previously (Wang et al., 2006). Crystals of the title compound were obtained by slow evaporation at 293 K of 1,2-dichoroethane/methanol (vol. 3:1) solution .

Structure description top

For the related structures, see: Chen et al. (2007); Hof et al.,(2002); Hu et al. (2007); Isaacs & Fettinger (1999); Wang et al. (2006). Cg2 is the centroid of the C21–C26 ring.

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. The molecular structure of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound

Diethyl 6,13-dioxo-5,7,12,13b,13c,14-hexahydro-6H,13H-5a,6a,12a,13a- tetraazabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-13b,13c- dicarboxylate 1,2-dichloroethane solvate top

Crystal data top

C₂₆H₂₆N₄O₆·C₂H₄Cl₂	Z = 2
M_r = 589.46	F(000) = 616
Triclinic, P1	D_x = 1.380 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9468 (10) Å	Cell parameters from 5260 reflections
b = 11.1544 (13) Å	θ = 2.3–26.1°
c = 15.6260 (18) Å	µ = 0.28 mm⁻¹
α = 69.257 (2)°	T = 292 K
β = 82.688 (2)°	Block, colorless
γ = 76.892 (2)°	0.30 × 0.20 × 0.10 mm
V = 1418.5 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4056 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
φ and ω scans	h = −10→10
10171 measured reflections	k = −13→13
4947 independent reflections	l = −18→18

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1032P)² + 0.8923P] where P = (F_o² + 2F_c²)/3
4947 reflections	(Δ/σ)_max = 0.001
383 parameters	Δρ_max = 0.69 e Å⁻³
28 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₂₆H₂₆N₄O₆·C₂H₄Cl₂	γ = 76.892 (2)°
M_r = 589.46	V = 1418.5 (3) Å³
Triclinic, P1	Z = 2
a = 8.9468 (10) Å	Mo Kα radiation
b = 11.1544 (13) Å	µ = 0.28 mm⁻¹
c = 15.6260 (18) Å	T = 292 K
α = 69.257 (2)°	0.30 × 0.20 × 0.10 mm
β = 82.688 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4056 reflections with I > 2σ(I)
10171 measured reflections	R_int = 0.020
4947 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	28 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.04	Δρ_max = 0.69 e Å⁻³
4947 reflections	Δρ_min = −0.64 e Å⁻³
383 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	Occ. (<1)
C1	0.3563 (3)	0.4517 (3)	0.43467 (17)	0.0419 (6)
C2	0.4101 (3)	0.3329 (3)	0.5006 (2)	0.0527 (7)
H2	0.3424	0.2944	0.5472	0.063*
C3	0.5627 (4)	0.2702 (3)	0.4988 (2)	0.0585 (8)
H3	0.5962	0.1900	0.5434	0.070*
C4	0.6644 (3)	0.3268 (3)	0.4308 (2)	0.0558 (8)
H4	0.7670	0.2856	0.4294	0.067*
C5	0.6127 (3)	0.4452 (3)	0.3650 (2)	0.0489 (7)
H5	0.6816	0.4833	0.3191	0.059*
C6	0.4600 (3)	0.5090 (3)	0.36552 (18)	0.0418 (6)
C7	0.4116 (3)	0.6394 (3)	0.29185 (19)	0.0477 (7)
H7A	0.3833	0.7071	0.3197	0.057*
H7B	0.4982	0.6589	0.2487	0.057*
C8	0.1895 (3)	0.5177 (3)	0.44266 (18)	0.0453 (6)
H8A	0.1394	0.4605	0.4949	0.054*
H8B	0.1866	0.5974	0.4552	0.054*
C9	0.2946 (3)	0.6387 (2)	0.15541 (18)	0.0398 (6)
C10	0.0566 (3)	0.4531 (2)	0.34105 (17)	0.0372 (6)
C11	0.1265 (3)	0.6567 (2)	0.27998 (17)	0.0378 (6)
C12	0.0736 (3)	0.7930 (3)	0.2899 (2)	0.0508 (7)
C14	−0.0459 (15)	0.9472 (8)	0.4212 (6)	0.128 (4)	0.702 (14)
H14A	−0.0458	0.8751	0.4776	0.192*	0.702 (14)
H14B	−0.0985	1.0265	0.4314	0.192*	0.702 (14)
H14C	0.0581	0.9543	0.3994	0.192*	0.702 (14)
C13	−0.1260 (11)	0.9249 (6)	0.3514 (6)	0.095 (3)	0.702 (14)
H13A	−0.2332	0.9230	0.3705	0.114*	0.702 (14)
H13B	−0.1203	0.9933	0.2925	0.114*	0.702 (14)
C15	0.0392 (3)	0.6362 (2)	0.20652 (16)	0.0368 (5)
C16	−0.1181 (3)	0.7301 (3)	0.18476 (19)	0.0444 (6)
C17	−0.2468 (4)	0.9420 (3)	0.1062 (3)	0.0680 (9)
H17A	−0.3236	0.9100	0.0863	0.082*
H17B	−0.2870	0.9616	0.1614	0.082*
C18	−0.2110 (6)	1.0594 (4)	0.0345 (3)	0.0979 (15)
H18A	−0.1399	1.0935	0.0562	0.147*
H18B	−0.3036	1.1239	0.0187	0.147*
H18C	−0.1658	1.0379	−0.0187	0.147*
C19	−0.0402 (3)	0.4324 (3)	0.20547 (18)	0.0429 (6)
H19A	−0.1262	0.4892	0.1699	0.052*
H19B	−0.0778	0.3591	0.2512	0.052*
C20	0.1259 (3)	0.6119 (3)	0.05267 (17)	0.0428 (6)
H20A	0.1919	0.6513	0.0009	0.051*
H20B	0.0205	0.6467	0.0350	0.051*
C21	0.0802 (3)	0.3813 (3)	0.14224 (17)	0.0419 (6)
C22	0.1590 (3)	0.4658 (3)	0.07154 (17)	0.0406 (6)
C23	0.2683 (3)	0.4133 (3)	0.01628 (19)	0.0493 (7)
H23	0.3224	0.4681	−0.0301	0.059*
C24	0.2981 (4)	0.2818 (3)	0.0286 (2)	0.0550 (7)
H24	0.3710	0.2487	−0.0095	0.066*
C25	0.2200 (4)	0.1994 (3)	0.0975 (2)	0.0572 (8)
H25	0.2394	0.1106	0.1059	0.069*
C26	0.1127 (3)	0.2490 (3)	0.1541 (2)	0.0497 (7)
H26	0.0611	0.1927	0.2011	0.060*
C27	0.4248 (6)	0.1793 (8)	0.3161 (4)	0.130 (2)
H27A	0.3189	0.2096	0.3335	0.156*
H27B	0.4875	0.1658	0.3663	0.156*
C28	0.4742 (5)	0.2807 (4)	0.2334 (4)	0.0969 (16)
H28A	0.4497	0.3640	0.2436	0.116*
H28B	0.4169	0.2891	0.1822	0.116*
Cl1	0.4405 (2)	0.03136 (15)	0.29818 (12)	0.1337 (6)
Cl2	0.67477 (15)	0.24467 (12)	0.20429 (9)	0.0987 (4)
N1	0.2825 (2)	0.6424 (2)	0.24224 (15)	0.0421 (5)
N2	0.1009 (2)	0.5506 (2)	0.36207 (14)	0.0387 (5)
N3	0.1477 (2)	0.6518 (2)	0.12931 (13)	0.0373 (5)
N4	0.0168 (2)	0.5040 (2)	0.25176 (14)	0.0392 (5)
O1	0.4116 (2)	0.6274 (2)	0.10852 (13)	0.0527 (5)
O2	0.0510 (2)	0.34424 (19)	0.39298 (13)	0.0516 (5)
O3	0.1344 (3)	0.8818 (2)	0.2469 (2)	0.0853 (8)
O4	−0.0449 (3)	0.7988 (2)	0.3460 (2)	0.0856 (8)
O5	−0.2343 (3)	0.7010 (3)	0.2211 (2)	0.0865 (9)
O6	−0.1047 (2)	0.84312 (19)	0.12437 (15)	0.0582 (6)
C14'	−0.178 (2)	0.9307 (14)	0.4359 (10)	0.083 (6)	0.298 (14)
H14D	−0.2692	0.9053	0.4272	0.125*	0.298 (14)
H14E	−0.2036	1.0188	0.4364	0.125*	0.298 (14)
H14F	−0.1368	0.8732	0.4933	0.125*	0.298 (14)
C13'	−0.062 (3)	0.9224 (17)	0.3593 (19)	0.109 (9)	0.298 (14)
H13C	−0.0937	0.9929	0.3033	0.131*	0.298 (14)
H13D	0.0366	0.9318	0.3737	0.131*	0.298 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0371 (13)	0.0563 (16)	0.0361 (13)	−0.0142 (11)	−0.0003 (10)	−0.0176 (12)
C2	0.0476 (16)	0.0627 (18)	0.0445 (15)	−0.0184 (13)	−0.0048 (12)	−0.0086 (13)
C3	0.0564 (19)	0.0537 (17)	0.0596 (18)	−0.0080 (14)	−0.0156 (15)	−0.0096 (14)
C4	0.0385 (15)	0.0658 (19)	0.068 (2)	−0.0054 (13)	−0.0085 (14)	−0.0292 (16)
C5	0.0338 (14)	0.0666 (18)	0.0494 (16)	−0.0145 (12)	0.0019 (12)	−0.0218 (14)
C6	0.0354 (13)	0.0540 (15)	0.0411 (14)	−0.0148 (11)	−0.0013 (11)	−0.0187 (12)
C7	0.0353 (14)	0.0592 (17)	0.0485 (15)	−0.0192 (12)	−0.0022 (11)	−0.0118 (13)
C8	0.0372 (14)	0.0653 (17)	0.0349 (13)	−0.0139 (12)	0.0024 (11)	−0.0176 (12)
C9	0.0352 (13)	0.0367 (13)	0.0410 (14)	−0.0095 (10)	0.0016 (11)	−0.0049 (10)
C10	0.0270 (12)	0.0450 (14)	0.0365 (13)	−0.0094 (10)	0.0044 (10)	−0.0105 (11)
C11	0.0305 (12)	0.0421 (13)	0.0402 (13)	−0.0094 (10)	0.0005 (10)	−0.0123 (11)
C12	0.0506 (17)	0.0498 (16)	0.0552 (17)	−0.0114 (13)	−0.0061 (14)	−0.0194 (14)
C14	0.196 (11)	0.081 (5)	0.103 (6)	0.005 (6)	−0.015 (6)	−0.044 (4)
C13	0.089 (5)	0.063 (4)	0.115 (5)	0.019 (3)	0.020 (4)	−0.036 (3)
C15	0.0323 (12)	0.0401 (13)	0.0359 (13)	−0.0097 (10)	0.0002 (10)	−0.0094 (10)
C16	0.0347 (14)	0.0491 (15)	0.0466 (15)	−0.0094 (11)	−0.0008 (11)	−0.0125 (12)
C17	0.0547 (19)	0.0559 (19)	0.076 (2)	0.0096 (15)	−0.0052 (16)	−0.0134 (16)
C18	0.099 (3)	0.054 (2)	0.103 (3)	0.013 (2)	0.000 (3)	0.000 (2)
C19	0.0405 (14)	0.0486 (15)	0.0423 (14)	−0.0183 (11)	0.0012 (11)	−0.0136 (12)
C20	0.0441 (14)	0.0478 (15)	0.0330 (13)	−0.0109 (11)	−0.0008 (11)	−0.0085 (11)
C21	0.0398 (14)	0.0502 (15)	0.0383 (13)	−0.0132 (11)	−0.0062 (11)	−0.0140 (11)
C22	0.0378 (13)	0.0494 (15)	0.0353 (13)	−0.0096 (11)	−0.0032 (10)	−0.0140 (11)
C23	0.0454 (15)	0.0612 (18)	0.0432 (15)	−0.0137 (13)	0.0013 (12)	−0.0189 (13)
C24	0.0495 (17)	0.0634 (19)	0.0596 (18)	−0.0066 (14)	0.0005 (14)	−0.0337 (15)
C25	0.0621 (19)	0.0514 (17)	0.0642 (19)	−0.0075 (14)	−0.0086 (15)	−0.0272 (15)
C26	0.0543 (17)	0.0487 (16)	0.0494 (16)	−0.0181 (13)	−0.0049 (13)	−0.0146 (13)
C27	0.073 (3)	0.229 (8)	0.118 (4)	−0.017 (4)	0.000 (3)	−0.105 (5)
C28	0.089 (3)	0.066 (2)	0.145 (4)	0.007 (2)	−0.055 (3)	−0.044 (3)
Cl1	0.1401 (13)	0.1025 (10)	0.1312 (12)	−0.0443 (9)	−0.0254 (10)	0.0126 (8)
Cl2	0.1068 (9)	0.0891 (8)	0.1020 (8)	−0.0310 (6)	0.0009 (7)	−0.0292 (6)
N1	0.0317 (11)	0.0554 (13)	0.0394 (12)	−0.0153 (9)	0.0016 (9)	−0.0134 (10)
N2	0.0312 (11)	0.0488 (12)	0.0351 (11)	−0.0116 (9)	0.0020 (8)	−0.0119 (9)
N3	0.0331 (11)	0.0408 (11)	0.0344 (11)	−0.0087 (8)	0.0027 (8)	−0.0090 (9)
N4	0.0401 (11)	0.0413 (11)	0.0369 (11)	−0.0146 (9)	0.0001 (9)	−0.0107 (9)
O1	0.0362 (10)	0.0659 (13)	0.0494 (11)	−0.0124 (9)	0.0105 (9)	−0.0143 (9)
O2	0.0540 (12)	0.0500 (11)	0.0436 (11)	−0.0175 (9)	−0.0005 (9)	−0.0034 (9)
O3	0.106 (2)	0.0513 (14)	0.101 (2)	−0.0313 (14)	0.0131 (17)	−0.0258 (14)
O4	0.0864 (18)	0.0585 (14)	0.101 (2)	−0.0014 (13)	0.0328 (16)	−0.0346 (14)
O5	0.0343 (12)	0.0731 (16)	0.119 (2)	−0.0072 (10)	0.0087 (13)	0.0011 (15)
O6	0.0463 (11)	0.0451 (11)	0.0637 (13)	0.0029 (9)	0.0031 (9)	−0.0041 (10)
C14'	0.103 (11)	0.060 (7)	0.082 (9)	0.005 (7)	−0.001 (8)	−0.031 (6)
C13'	0.102 (12)	0.102 (11)	0.117 (12)	−0.003 (8)	0.006 (9)	−0.044 (8)

Geometric parameters (Å, º) top

C1—C2	1.385 (4)	C16—O6	1.300 (3)
C1—C6	1.401 (4)	C17—C18	1.460 (5)
C1—C8	1.518 (4)	C17—O6	1.465 (4)
C2—C3	1.388 (4)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.377 (5)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C5	1.377 (4)	C18—H18C	0.9600
C4—H4	0.9300	C19—N4	1.453 (3)
C5—C6	1.391 (4)	C19—C21	1.520 (4)
C5—H5	0.9300	C19—H19A	0.9700
C6—C7	1.511 (4)	C19—H19B	0.9700
C7—N1	1.459 (3)	C20—N3	1.466 (3)
C7—H7A	0.9700	C20—C22	1.515 (4)
C7—H7B	0.9700	C20—H20A	0.9700
C8—N2	1.464 (3)	C20—H20B	0.9700
C8—H8A	0.9700	C21—C26	1.387 (4)
C8—H8B	0.9700	C21—C22	1.403 (4)
C9—O1	1.208 (3)	C22—C23	1.389 (4)
C9—N1	1.362 (3)	C23—C24	1.376 (4)
C9—N3	1.386 (3)	C23—H23	0.9300
C10—O2	1.206 (3)	C24—C25	1.375 (5)
C10—N4	1.367 (3)	C24—H24	0.9300
C10—N2	1.389 (3)	C25—C26	1.378 (4)
C11—N2	1.439 (3)	C25—H25	0.9300
C11—N1	1.441 (3)	C26—H26	0.9300
C11—C12	1.543 (4)	C27—C28	1.480 (8)
C11—C15	1.573 (3)	C27—Cl1	1.742 (7)
C12—O3	1.186 (4)	C27—H27A	0.9700
C12—O4	1.292 (4)	C27—H27B	0.9700
C14—C13	1.496 (8)	C28—Cl2	1.784 (5)
C14—H14A	0.9600	C28—H28A	0.9700
C14—H14B	0.9600	C28—H28B	0.9700
C14—H14C	0.9600	O4—C13'	1.438 (9)
C13—O4	1.455 (5)	C14'—C13'	1.500 (9)
C13—H13A	0.9700	C14'—H14D	0.9600
C13—H13B	0.9700	C14'—H14E	0.9600
C15—N3	1.435 (3)	C14'—H14F	0.9600
C15—N4	1.440 (3)	C13'—H13C	0.9700
C15—C16	1.547 (4)	C13'—H13D	0.9700
C16—O5	1.175 (3)

C2—C1—C6	118.6 (3)	H18B—C18—H18C	109.5
C2—C1—C8	118.8 (2)	N4—C19—C21	113.5 (2)
C6—C1—C8	122.5 (2)	N4—C19—H19A	108.9
C1—C2—C3	121.4 (3)	C21—C19—H19A	108.9
C1—C2—H2	119.3	N4—C19—H19B	108.9
C3—C2—H2	119.3	C21—C19—H19B	108.9
C4—C3—C2	119.8 (3)	H19A—C19—H19B	107.7
C4—C3—H3	120.1	N3—C20—C22	115.3 (2)
C2—C3—H3	120.1	N3—C20—H20A	108.4
C3—C4—C5	119.3 (3)	C22—C20—H20A	108.4
C3—C4—H4	120.3	N3—C20—H20B	108.4
C5—C4—H4	120.3	C22—C20—H20B	108.4
C4—C5—C6	121.6 (3)	H20A—C20—H20B	107.5
C4—C5—H5	119.2	C26—C21—C22	119.2 (3)
C6—C5—H5	119.2	C26—C21—C19	119.6 (2)
C5—C6—C1	119.2 (3)	C22—C21—C19	121.3 (2)
C5—C6—C7	118.8 (2)	C23—C22—C21	118.6 (3)
C1—C6—C7	122.0 (2)	C23—C22—C20	119.3 (2)
N1—C7—C6	112.8 (2)	C21—C22—C20	122.1 (2)
N1—C7—H7A	109.0	C24—C23—C22	121.4 (3)
C6—C7—H7A	109.0	C24—C23—H23	119.3
N1—C7—H7B	109.0	C22—C23—H23	119.3
C6—C7—H7B	109.0	C25—C24—C23	119.9 (3)
H7A—C7—H7B	107.8	C25—C24—H24	120.0
N2—C8—C1	115.4 (2)	C23—C24—H24	120.0
N2—C8—H8A	108.4	C24—C25—C26	119.7 (3)
C1—C8—H8A	108.4	C24—C25—H25	120.1
N2—C8—H8B	108.4	C26—C25—H25	120.1
C1—C8—H8B	108.4	C25—C26—C21	121.2 (3)
H8A—C8—H8B	107.5	C25—C26—H26	119.4
O1—C9—N1	126.6 (2)	C21—C26—H26	119.4
O1—C9—N3	125.6 (2)	C28—C27—Cl1	112.0 (4)
N1—C9—N3	107.8 (2)	C28—C27—H27A	109.2
O2—C10—N4	126.3 (2)	Cl1—C27—H27A	109.2
O2—C10—N2	126.0 (2)	C28—C27—H27B	109.2
N4—C10—N2	107.6 (2)	Cl1—C27—H27B	109.2
N2—C11—N1	113.7 (2)	H27A—C27—H27B	107.9
N2—C11—C12	113.9 (2)	C27—C28—Cl2	112.9 (3)
N1—C11—C12	110.0 (2)	C27—C28—H28A	109.0
N2—C11—C15	103.24 (19)	Cl2—C28—H28A	109.0
N1—C11—C15	101.53 (19)	C27—C28—H28B	109.0
C12—C11—C15	113.7 (2)	Cl2—C28—H28B	109.0
O3—C12—O4	125.4 (3)	H28A—C28—H28B	107.8
O3—C12—C11	122.0 (3)	C9—N1—C11	113.3 (2)
O4—C12—C11	112.6 (2)	C9—N1—C7	124.3 (2)
O4—C13—C14	105.1 (6)	C11—N1—C7	122.2 (2)
O4—C13—H13A	110.7	C10—N2—C11	110.7 (2)
C14—C13—H13A	110.7	C10—N2—C8	120.4 (2)
O4—C13—H13B	110.7	C11—N2—C8	120.6 (2)
C14—C13—H13B	110.7	C9—N3—C15	111.0 (2)
H13A—C13—H13B	108.8	C9—N3—C20	120.1 (2)
N3—C15—N4	114.1 (2)	C15—N3—C20	120.6 (2)
N3—C15—C16	113.7 (2)	C10—N4—C15	113.5 (2)
N4—C15—C16	109.9 (2)	C10—N4—C19	123.9 (2)
N3—C15—C11	103.08 (18)	C15—N4—C19	122.6 (2)
N4—C15—C11	101.56 (19)	C12—O4—C13'	105.1 (7)
C16—C15—C11	113.7 (2)	C12—O4—C13	119.7 (5)
O5—C16—O6	125.1 (3)	C13'—O4—C13	23.8 (11)
O5—C16—C15	122.6 (3)	C16—O6—C17	115.7 (2)
O6—C16—C15	112.2 (2)	C13'—C14'—H14D	109.5
C18—C17—O6	107.9 (3)	C13'—C14'—H14E	109.5
C18—C17—H17A	110.1	H14D—C14'—H14E	109.5
O6—C17—H17A	110.1	C13'—C14'—H14F	109.5
C18—C17—H17B	110.1	H14D—C14'—H14F	109.5
O6—C17—H17B	110.1	H14E—C14'—H14F	109.5
H17A—C17—H17B	108.4	O4—C13'—C14'	110.2 (11)
C17—C18—H18A	109.5	O4—C13'—H13C	109.6
C17—C18—H18B	109.5	C14'—C13'—H13C	109.6
H18A—C18—H18B	109.5	O4—C13'—H13D	109.6
C17—C18—H18C	109.5	C14'—C13'—H13D	109.6
H18A—C18—H18C	109.5	H13C—C13'—H13D	108.1

C6—C1—C2—C3	−0.6 (4)	N2—C11—N1—C9	120.0 (2)
C8—C1—C2—C3	−177.7 (3)	C12—C11—N1—C9	−110.9 (2)
C1—C2—C3—C4	0.7 (5)	C15—C11—N1—C9	9.8 (3)
C2—C3—C4—C5	−0.4 (5)	N2—C11—N1—C7	−63.1 (3)
C3—C4—C5—C6	0.1 (5)	C12—C11—N1—C7	66.1 (3)
C4—C5—C6—C1	0.0 (4)	C15—C11—N1—C7	−173.2 (2)
C4—C5—C6—C7	179.3 (3)	C6—C7—N1—C9	−105.6 (3)
C2—C1—C6—C5	0.3 (4)	C6—C7—N1—C11	77.8 (3)
C8—C1—C6—C5	177.2 (2)	O2—C10—N2—C11	167.3 (2)
C2—C1—C6—C7	−179.0 (3)	N4—C10—N2—C11	−14.3 (3)
C8—C1—C6—C7	−2.0 (4)	O2—C10—N2—C8	18.7 (4)
C5—C6—C7—N1	125.7 (3)	N4—C10—N2—C8	−162.9 (2)
C1—C6—C7—N1	−55.0 (4)	N1—C11—N2—C10	−90.4 (2)
C2—C1—C8—N2	−125.1 (3)	C12—C11—N2—C10	142.5 (2)
C6—C1—C8—N2	57.9 (4)	C15—C11—N2—C10	18.7 (2)
N2—C11—C12—O3	150.2 (3)	N1—C11—N2—C8	58.1 (3)
N1—C11—C12—O3	21.2 (4)	C12—C11—N2—C8	−69.0 (3)
C15—C11—C12—O3	−91.9 (3)	C15—C11—N2—C8	167.2 (2)
N2—C11—C12—O4	−32.4 (3)	C1—C8—N2—C10	72.8 (3)
N1—C11—C12—O4	−161.4 (3)	C1—C8—N2—C11	−72.7 (3)
C15—C11—C12—O4	85.6 (3)	O1—C9—N3—C15	168.2 (2)
N2—C11—C15—N3	−134.01 (19)	N1—C9—N3—C15	−12.5 (3)
N1—C11—C15—N3	−16.0 (2)	O1—C9—N3—C20	19.6 (4)
C12—C11—C15—N3	102.1 (2)	N1—C9—N3—C20	−161.1 (2)
N2—C11—C15—N4	−15.6 (2)	N4—C15—N3—C9	−91.4 (2)
N1—C11—C15—N4	102.4 (2)	C16—C15—N3—C9	141.5 (2)
C12—C11—C15—N4	−139.5 (2)	C11—C15—N3—C9	17.9 (3)
N2—C11—C15—C16	102.4 (2)	N4—C15—N3—C20	57.1 (3)
N1—C11—C15—C16	−139.6 (2)	C16—C15—N3—C20	−70.1 (3)
C12—C11—C15—C16	−21.5 (3)	C11—C15—N3—C20	166.3 (2)
N3—C15—C16—O5	147.3 (3)	C22—C20—N3—C9	71.6 (3)
N4—C15—C16—O5	18.0 (4)	C22—C20—N3—C15	−74.0 (3)
C11—C15—C16—O5	−95.1 (3)	O2—C10—N4—C15	−178.7 (2)
N3—C15—C16—O6	−34.2 (3)	N2—C10—N4—C15	2.9 (3)
N4—C15—C16—O6	−163.5 (2)	O2—C10—N4—C19	0.3 (4)
C11—C15—C16—O6	83.4 (3)	N2—C10—N4—C19	−178.1 (2)
N4—C19—C21—C26	124.3 (3)	N3—C15—N4—C10	118.4 (2)
N4—C19—C21—C22	−56.0 (3)	C16—C15—N4—C10	−112.5 (2)
C26—C21—C22—C23	−0.7 (4)	C11—C15—N4—C10	8.3 (3)
C19—C21—C22—C23	179.7 (2)	N3—C15—N4—C19	−60.6 (3)
C26—C21—C22—C20	178.0 (2)	C16—C15—N4—C19	68.5 (3)
C19—C21—C22—C20	−1.6 (4)	C11—C15—N4—C19	−170.8 (2)
N3—C20—C22—C23	−122.5 (3)	C21—C19—N4—C10	−102.0 (3)
N3—C20—C22—C21	58.8 (3)	C21—C19—N4—C15	76.9 (3)
C21—C22—C23—C24	1.2 (4)	O3—C12—O4—C13'	−12.5 (15)
C20—C22—C23—C24	−177.6 (3)	C11—C12—O4—C13'	170.2 (14)
C22—C23—C24—C25	−0.7 (4)	O3—C12—O4—C13	8.0 (7)
C23—C24—C25—C26	−0.4 (5)	C11—C12—O4—C13	−169.3 (5)
C24—C25—C26—C21	0.8 (4)	C14—C13—O4—C12	−88.2 (9)
C22—C21—C26—C25	−0.3 (4)	C14—C13—O4—C13'	−32 (3)
C19—C21—C26—C25	179.3 (3)	O5—C16—O6—C17	4.0 (5)
Cl1—C27—C28—Cl2	−66.8 (4)	C15—C16—O6—C17	−174.5 (3)
O1—C9—N1—C11	−180.0 (2)	C18—C17—O6—C16	−177.6 (3)
N3—C9—N1—C11	0.7 (3)	C12—O4—C13'—C14'	−170.1 (18)
O1—C9—N1—C7	3.2 (4)	C13—O4—C13'—C14'	58.7 (18)
N3—C9—N1—C7	−176.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28B···Cg2	0.97	2.55	3.476 (3)	160
C5—H5···O5ⁱ	0.93	2.59	3.393 (4)	145
C7—H7B···O5ⁱ	0.97	2.50	3.359 (3)	148
C14—H14A···O2ⁱⁱ	0.96	2.57	3.514 (9)	168
C14′—H14F···O2ⁱⁱ	0.96	2.47	3.351 (6)	153

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆N₄O₆·C₂H₄Cl₂
M_r	589.46
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	8.9468 (10), 11.1544 (13), 15.6260 (18)
α, β, γ (°)	69.257 (2), 82.688 (2), 76.892 (2)
V (Å³)	1418.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10171, 4947, 4056
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.188, 1.04
No. of reflections	4947
No. of parameters	383
No. of restraints	28
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.64

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
C28—H28B···Cg2	0.97	2.55	3.476 (3)	160
C5—H5···O5ⁱ	0.93	2.59	3.393 (4)	145
C7—H7B···O5ⁱ	0.97	2.50	3.359 (3)	148
C14—H14A···O2ⁱⁱ	0.96	2.57	3.514 (9)	168
C14'—H14F···O2ⁱⁱ	0.96	2.47	3.351 (6)	153

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

Acknowledgements

This study was financially supported by Huangshi Institute of Technology (B20083002).

References

Bruker (2001). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Y. F., She, N. F., Meng, X. G., Yin, G. D., Wu, A. X. & Isaacs, L. (2007). Org. Lett. 9, 1899–1902. Web of Science CrossRef PubMed CAS Google Scholar
Hof, F., Craig, S. L., Nuckolls, C. & Rebek, J. Jr (2002). Angew. Chem. Int. Ed. 41, 1488–1508. Web of Science CrossRef CAS Google Scholar
Hu, S. L., She, N. F., Yin, G. D., Guo, H. Z., Wu, A. X. & Yang, C. L. (2007). Tetrahedron. Lett. 48, 1591–1594. Web of Science CSD CrossRef CAS Google Scholar
Isaacs, L. & Fettinger, J. C. (1999). Chem. Commun. 24, 2549–2550. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z. G., Zhou, B. H., Chen, Y. F., Yin, G. D., Li, Y. T., Wu, A. X. & Isaacs, L. (2006). J. Org. Chem. 71, 4502–4508. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 65| Part 11| November 2009| Pages o2746-o2747

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

Di­ethyl 6,13-dioxo-5,7,12,13b,13c,14-hexa­hydro-6H,13H-5a,6a,12a,13a-tetra­azabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-13b,13c-di­carboxyl­ate 1,2-di­chloro­ethane solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Diethyl 6,13-dioxo-5,7,12,13b,13c,14-hexahydro-6H,13H-5a,6a,12a,13a-tetraazabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-13b,13c-dicarboxylate 1,2-dichloroethane solvate