3,22-Dioxa-11,14-di­aza­penta­cyclo­[12.8.0.02,11.05,10.015,20]docosa-5(10),6,8,15(20),16,18-hexa­ene-4,21-dione

Ren, X.; Feng, J.; Wang, J.; Liu, B.; Yang, B.

doi:10.1107/S1600536813024537

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1535

doi:10.1107/S1600536813024537

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3,22-Dioxa-11,14-diazapentacyclo[12.8.0.0^2,11.0^5,10.0^15,20]docosa-5(10),6,8,15(20),16,18-hexaene-4,21-dione

Xiaolin Ren,^a Jiao Feng,^a Jinglin Wang,^b Bin Liu ^a and Binsheng Yang ^a ^*

^aInstitute of Molecular Science, Chemical Biology and Molecular Engineering Laboratory of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China, and ^bDepartment of Chemistry, Changzhi University, Changzhi, Shanxi 046011, People's Republic of China
^*Correspondence e-mail: yangbs@sxu.edu.cn

(Received 31 August 2013; accepted 3 September 2013; online 12 September 2013)

In the title compound, C₁₈H₁₄N₂O₄, the piperazine ring adopts a chair conformation and the dihedral angle between the aromatic rings is 13.09 (9)°. In the crystal, molecules are linked along the c axis by C—H⋯π and N⋯π [H(N)–centroid distances = 2.8030 (2) and 3.376 (2) Å] interactions between neighbouring molecules.

Related literature

For applications of π–π interactions, see: Janiak (2000 ). For C—H⋯π interactions, see: Ciunik & Desiraju (2001 ) and for N⋯π interactions, see: Lindeman et al. (1998 ). For the synthesis of the 2,2′-(ethane-1,2-diylbis(azanediyl))dibenzoic acid precursor, see: Berger & Telford (2002 ).

Experimental

Crystal data

C₁₈H₁₄N₂O₄
M_r = 322.31
Triclinic, $[P \overline 1]$
a = 8.058 (1) Å
b = 8.2629 (11) Å
c = 12.0972 (14) Å
α = 74.956 (2)°
β = 73.868 (1)°
γ = 72.311 (1)°
V = 723.54 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.23 × 0.20 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.976, T_max = 0.986
3858 measured reflections
2533 independent reflections
1301 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.098
S = 1.01
2533 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1ⁱ	0.98	2.80	3.7337 (3)	159
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); 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) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813024537/ff2118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813024537/ff2118Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813024537/ff2118Isup3.cml

checkCIF report

Comment top

The C–H···π and π–π interactions are important noncovalent intermolecular forces in determining the crystal packing, molecular assemblies, and structures of large biological systems (Janiak, 2000). In the present work, the crystal of the title compound is generated by noncovalent interactions.

In the title molecule (Fig. 1), the piperazine ring adopts a chair conformation and the dihedral angle between two phenyl rings (C6—C11; C13—C18) is 13.09 (9)°.

As shown in Figure 2, the neighboring molecules of title compound are arranged in a mutual head-to-tail manner by C–H···Cg1ⁱ (Cg1 is the centroid of the C6—C11 benzene ring) interactions (black dotted lines) and N···Cg2ⁱⁱ (Cg2 is the centroid of the C13—C18 benzene ring) interactions (pink dotted lines)to form infinite one-dimensional chain structure along the c axis [symmetry code: (i) 1 - x, 1 - y,1 - z; (ii)1 - x, 1 - y, 2 - z].

The adjacent one-dimensional chains, by van der Waals contacts, stack in a side-by-side fashion along the c axis to form three-dimensional structure (Fig. 3).

Related literature top

For applications of π–π interactions, see: Janiak (2000). For C—H···π interactions, see: Ciunik & Desiraju (2001) and for N···π interactions, see: Lindeman et al. (1998). For the synthesis of the 2,2'-(ethane-1,2-diylbis(azanediyl))dibenzoic acid precursor, see: Berger & Telford (2002).

Experimental top

The precursor 2,2'-(ethane-1,2-diylbis(azanediyl))dibenzoic acid (EDA) was synthesized according to literature procedures (Berger et al., 2002). The title compound was prepared by stirring a methanolic solution of EDA (300 mg, 1.0 mmol) and triethylamine (1 ml) for 10 min at room temperature. Then, 10 ml of a methanol solution containing CuCl₂·2H₂O(170 mg, 1 mmol) was added to the mixture and refluxed for 2 h. The mixture was filtered and washed with methanol. The EDA-Cu compound is not achieved as predicted. However, orange single crystals of the title complex suitable for X-ray analysis were obtained after several days from the mother liquor by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. The one-dimensional chain structure of the title compound is formed by N···π interactions (pink dotted lines) and C–H···π interactions (black dotted lines) and extending along the c axis (all distances in Å).
	Fig. 3. Packing of the title compound viewed along the c axis

3,22-Dioxa-11,14-diazapentacyclo[12.8.0.0^2,11.0^5,10.0^15,20]docosa-5(10),6,8,15 (20),16,18-hexaene-4,21-dione top

Crystal data top

C₁₈H₁₄N₂O₄	Z = 2
M_r = 322.31	F(000) = 336
Triclinic, P1	D_x = 1.479 Mg m⁻³
a = 8.058 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2629 (11) Å	Cell parameters from 695 reflections
c = 12.0972 (14) Å	θ = 2.6–22.8°
α = 74.956 (2)°	µ = 0.11 mm⁻¹
β = 73.868 (1)°	T = 293 K
γ = 72.311 (1)°	Block, orange
V = 723.54 (16) Å³	0.23 × 0.20 × 0.13 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2533 independent reflections
Radiation source: fine-focus sealed tube	1301 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→9
T_min = 0.976, T_max = 0.986	k = −9→9
3858 measured reflections	l = −14→12

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0216P)²] where P = (F_o² + 2F_c²)/3
2533 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₁₄N₂O₄	γ = 72.311 (1)°
M_r = 322.31	V = 723.54 (16) Å³
Triclinic, P1	Z = 2
a = 8.058 (1) Å	Mo Kα radiation
b = 8.2629 (11) Å	µ = 0.11 mm⁻¹
c = 12.0972 (14) Å	T = 293 K
α = 74.956 (2)°	0.23 × 0.20 × 0.13 mm
β = 73.868 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2533 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1301 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.986	R_int = 0.025
3858 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
2533 reflections	Δρ_min = −0.19 e Å⁻³
217 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
N1	0.5762 (3)	0.3589 (3)	0.6287 (2)	0.0388 (6)
N2	0.4532 (3)	0.5027 (3)	0.8359 (2)	0.0397 (6)
O1	0.7212 (2)	0.5863 (2)	0.54220 (16)	0.0450 (5)
O2	0.8892 (2)	0.6033 (3)	0.36520 (18)	0.0583 (6)
O3	0.6612 (2)	0.6710 (2)	0.75579 (16)	0.0481 (5)
O4	0.6823 (3)	0.8514 (3)	0.85352 (18)	0.0624 (6)
C1	0.6664 (3)	0.4729 (3)	0.6484 (2)	0.0390 (7)
H1	0.7706	0.4040	0.6809	0.047*
C2	0.5451 (3)	0.5917 (3)	0.7294 (2)	0.0388 (7)
H2	0.4584	0.6804	0.6886	0.047*
C3	0.3676 (3)	0.3824 (3)	0.8175 (2)	0.0485 (8)
H3A	0.2659	0.4473	0.7830	0.058*
H3B	0.3242	0.3144	0.8926	0.058*
C4	0.4938 (4)	0.2636 (4)	0.7389 (2)	0.0494 (8)
H4A	0.5862	0.1867	0.7786	0.059*
H4B	0.4296	0.1932	0.7229	0.059*
C5	0.8153 (4)	0.5144 (4)	0.4472 (3)	0.0441 (8)
C6	0.8080 (4)	0.3362 (4)	0.4543 (3)	0.0415 (7)
C7	0.6848 (4)	0.2634 (3)	0.5421 (3)	0.0398 (7)
C8	0.6709 (4)	0.1016 (4)	0.5381 (3)	0.0527 (8)
H8	0.5882	0.0506	0.5955	0.063*
C9	0.7781 (4)	0.0164 (4)	0.4503 (3)	0.0610 (9)
H9	0.7666	−0.0916	0.4486	0.073*
C10	0.9023 (4)	0.0876 (4)	0.3648 (3)	0.0623 (10)
H10	0.9759	0.0275	0.3065	0.075*
C11	0.9168 (4)	0.2484 (4)	0.3660 (3)	0.0547 (9)
H11	0.9993	0.2985	0.3078	0.066*
C12	0.5914 (4)	0.7686 (4)	0.8402 (3)	0.0468 (8)
C13	0.4154 (4)	0.7550 (4)	0.9111 (2)	0.0420 (7)
C14	0.3523 (4)	0.6153 (4)	0.9128 (2)	0.0419 (7)
C15	0.1977 (4)	0.5903 (4)	0.9944 (3)	0.0554 (9)
H15	0.1545	0.4958	0.9991	0.066*
C16	0.1090 (4)	0.7063 (5)	1.0681 (3)	0.0658 (10)
H16	0.0060	0.6882	1.1226	0.079*
C17	0.1676 (4)	0.8473 (4)	1.0639 (3)	0.0652 (10)
H17	0.1038	0.9257	1.1130	0.078*
C18	0.3217 (4)	0.8707 (4)	0.9860 (3)	0.0561 (9)
H18	0.3643	0.9648	0.9830	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0462 (14)	0.0398 (14)	0.0361 (15)	−0.0196 (11)	−0.0053 (13)	−0.0104 (12)
N2	0.0460 (14)	0.0456 (15)	0.0318 (15)	−0.0205 (11)	−0.0029 (12)	−0.0100 (12)
O1	0.0564 (13)	0.0462 (12)	0.0346 (13)	−0.0208 (10)	−0.0007 (11)	−0.0122 (11)
O2	0.0621 (14)	0.0704 (16)	0.0456 (14)	−0.0305 (12)	0.0059 (12)	−0.0188 (12)
O3	0.0530 (12)	0.0557 (13)	0.0465 (13)	−0.0281 (10)	0.0007 (11)	−0.0234 (11)
O4	0.0723 (15)	0.0659 (15)	0.0631 (16)	−0.0366 (11)	−0.0022 (12)	−0.0268 (12)
C1	0.0440 (17)	0.0419 (18)	0.0337 (18)	−0.0148 (14)	−0.0061 (15)	−0.0090 (15)
C2	0.0437 (17)	0.0441 (18)	0.0350 (18)	−0.0152 (13)	−0.0070 (15)	−0.0148 (15)
C3	0.0548 (19)	0.058 (2)	0.039 (2)	−0.0284 (16)	−0.0044 (16)	−0.0099 (17)
C4	0.063 (2)	0.0487 (19)	0.044 (2)	−0.0257 (15)	−0.0117 (17)	−0.0083 (17)
C5	0.0393 (18)	0.058 (2)	0.037 (2)	−0.0149 (15)	−0.0047 (16)	−0.0143 (18)
C6	0.0414 (18)	0.0430 (18)	0.044 (2)	−0.0074 (14)	−0.0105 (16)	−0.0172 (16)
C7	0.0449 (18)	0.0387 (17)	0.0404 (19)	−0.0071 (14)	−0.0157 (16)	−0.0125 (16)
C8	0.066 (2)	0.0438 (19)	0.055 (2)	−0.0168 (15)	−0.0167 (18)	−0.0139 (18)
C9	0.077 (3)	0.045 (2)	0.068 (3)	−0.0081 (18)	−0.023 (2)	−0.022 (2)
C10	0.064 (2)	0.059 (2)	0.064 (3)	0.0005 (18)	−0.013 (2)	−0.032 (2)
C11	0.0494 (19)	0.062 (2)	0.053 (2)	−0.0088 (16)	−0.0069 (17)	−0.0213 (19)
C12	0.060 (2)	0.0441 (19)	0.041 (2)	−0.0139 (16)	−0.0116 (17)	−0.0147 (16)
C13	0.0457 (18)	0.0486 (19)	0.0317 (18)	−0.0102 (14)	−0.0056 (15)	−0.0125 (15)
C14	0.0414 (18)	0.052 (2)	0.0321 (18)	−0.0112 (15)	−0.0084 (15)	−0.0083 (16)
C15	0.049 (2)	0.075 (2)	0.047 (2)	−0.0219 (17)	−0.0087 (18)	−0.0140 (19)
C16	0.046 (2)	0.100 (3)	0.051 (2)	−0.0181 (19)	0.0043 (18)	−0.031 (2)
C17	0.060 (2)	0.083 (3)	0.052 (2)	−0.0044 (19)	−0.007 (2)	−0.033 (2)
C18	0.062 (2)	0.056 (2)	0.051 (2)	−0.0088 (17)	−0.0126 (19)	−0.0195 (18)

Geometric parameters (Å, º) top

N1—C7	1.410 (3)	C6—C7	1.385 (4)
N1—C1	1.450 (3)	C6—C11	1.390 (3)
N1—C4	1.456 (3)	C7—C8	1.389 (3)
N2—C14	1.401 (3)	C8—C9	1.371 (4)
N2—C2	1.435 (3)	C8—H8	0.9300
N2—C3	1.459 (3)	C9—C10	1.373 (4)
O1—C5	1.359 (3)	C9—H9	0.9300
O1—C1	1.426 (3)	C10—C11	1.373 (4)
O2—C5	1.199 (3)	C10—H10	0.9300
O3—C12	1.357 (3)	C11—H11	0.9300
O3—C2	1.433 (3)	C12—C13	1.460 (3)
O4—C12	1.208 (3)	C13—C14	1.389 (3)
C1—C2	1.504 (3)	C13—C18	1.391 (3)
C1—H1	0.9800	C14—C15	1.391 (3)
C2—H2	0.9800	C15—C16	1.378 (4)
C3—C4	1.497 (3)	C15—H15	0.9300
C3—H3A	0.9700	C16—C17	1.368 (4)
C3—H3B	0.9700	C16—H16	0.9300
C4—H4A	0.9700	C17—C18	1.367 (4)
C4—H4B	0.9700	C17—H17	0.9300
C5—C6	1.471 (4)	C18—H18	0.9300

C7—N1—C1	111.2 (2)	C11—C6—C5	118.5 (3)
C7—N1—C4	117.6 (2)	C6—C7—C8	118.1 (3)
C1—N1—C4	111.3 (2)	C6—C7—N1	118.6 (3)
C14—N2—C2	111.6 (2)	C8—C7—N1	123.2 (3)
C14—N2—C3	117.4 (2)	C9—C8—C7	120.5 (3)
C2—N2—C3	113.7 (2)	C9—C8—H8	119.7
C5—O1—C1	117.6 (2)	C7—C8—H8	119.7
C12—O3—C2	117.6 (2)	C8—C9—C10	121.1 (3)
O1—C1—N1	111.1 (2)	C8—C9—H9	119.4
O1—C1—C2	104.5 (2)	C10—C9—H9	119.4
N1—C1—C2	112.0 (2)	C11—C10—C9	119.4 (3)
O1—C1—H1	109.7	C11—C10—H10	120.3
N1—C1—H1	109.7	C9—C10—H10	120.3
C2—C1—H1	109.7	C10—C11—C6	119.9 (3)
O3—C2—N2	109.6 (2)	C10—C11—H11	120.0
O3—C2—C1	104.6 (2)	C6—C11—H11	120.0
N2—C2—C1	113.3 (2)	O4—C12—O3	117.8 (3)
O3—C2—H2	109.7	O4—C12—C13	126.2 (3)
N2—C2—H2	109.7	O3—C12—C13	116.0 (3)
C1—C2—H2	109.7	C14—C13—C18	120.6 (3)
N2—C3—C4	111.6 (2)	C14—C13—C12	119.4 (3)
N2—C3—H3A	109.3	C18—C13—C12	119.6 (3)
C4—C3—H3A	109.3	C13—C14—C15	118.3 (3)
N2—C3—H3B	109.3	C13—C14—N2	117.9 (3)
C4—C3—H3B	109.3	C15—C14—N2	123.7 (3)
H3A—C3—H3B	108.0	C16—C15—C14	119.6 (3)
N1—C4—C3	111.8 (2)	C16—C15—H15	120.2
N1—C4—H4A	109.3	C14—C15—H15	120.2
C3—C4—H4A	109.3	C17—C16—C15	122.1 (3)
N1—C4—H4B	109.3	C17—C16—H16	119.0
C3—C4—H4B	109.3	C15—C16—H16	119.0
H4A—C4—H4B	107.9	C18—C17—C16	118.7 (3)
O2—C5—O1	117.5 (3)	C18—C17—H17	120.6
O2—C5—C6	126.8 (3)	C16—C17—H17	120.6
O1—C5—C6	115.6 (3)	C17—C18—C13	120.6 (3)
C7—C6—C11	120.9 (3)	C17—C18—H18	119.7
C7—C6—C5	120.4 (3)	C13—C18—H18	119.7

C5—O1—C1—N1	−51.0 (3)	C4—N1—C7—C6	−159.6 (2)
C5—O1—C1—C2	−172.0 (2)	C1—N1—C7—C8	152.4 (3)
C7—N1—C1—O1	56.5 (3)	C4—N1—C7—C8	22.5 (4)
C4—N1—C1—O1	−170.4 (2)	C6—C7—C8—C9	0.8 (4)
C7—N1—C1—C2	172.9 (2)	N1—C7—C8—C9	178.7 (3)
C4—N1—C1—C2	−53.9 (3)	C7—C8—C9—C10	0.4 (5)
C12—O3—C2—N2	−49.7 (3)	C8—C9—C10—C11	−1.3 (5)
C12—O3—C2—C1	−171.4 (2)	C9—C10—C11—C6	0.9 (4)
C14—N2—C2—O3	59.1 (3)	C7—C6—C11—C10	0.3 (4)
C3—N2—C2—O3	−165.26 (19)	C5—C6—C11—C10	−174.5 (3)
C14—N2—C2—C1	175.4 (2)	C2—O3—C12—O4	−171.7 (2)
C3—N2—C2—C1	−48.9 (3)	C2—O3—C12—C13	11.6 (4)
O1—C1—C2—O3	−69.7 (2)	O4—C12—C13—C14	−158.6 (3)
N1—C1—C2—O3	169.9 (2)	O3—C12—C13—C14	17.8 (4)
O1—C1—C2—N2	170.9 (2)	O4—C12—C13—C18	14.2 (4)
N1—C1—C2—N2	50.6 (3)	O3—C12—C13—C18	−169.5 (3)
C14—N2—C3—C4	−176.7 (2)	C18—C13—C14—C15	−2.6 (4)
C2—N2—C3—C4	50.3 (3)	C12—C13—C14—C15	170.1 (2)
C7—N1—C4—C3	−174.0 (2)	C18—C13—C14—N2	−179.6 (2)
C1—N1—C4—C3	56.1 (3)	C12—C13—C14—N2	−6.9 (4)
N2—C3—C4—N1	−53.7 (3)	C2—N2—C14—C13	−31.8 (3)
C1—O1—C5—O2	−166.5 (2)	C3—N2—C14—C13	−165.6 (2)
C1—O1—C5—C6	16.3 (3)	C2—N2—C14—C15	151.4 (3)
O2—C5—C6—C7	−164.6 (3)	C3—N2—C14—C15	17.6 (4)
O1—C5—C6—C7	12.2 (4)	C13—C14—C15—C16	1.9 (4)
O2—C5—C6—C11	10.1 (4)	N2—C14—C15—C16	178.7 (3)
O1—C5—C6—C11	−173.0 (2)	C14—C15—C16—C17	0.3 (5)
C11—C6—C7—C8	−1.1 (4)	C15—C16—C17—C18	−1.8 (5)
C5—C6—C7—C8	173.5 (2)	C16—C17—C18—C13	1.1 (5)
C11—C6—C7—N1	−179.2 (2)	C14—C13—C18—C17	1.1 (4)
C5—C6—C7—N1	−4.5 (4)	C12—C13—C18—C17	−171.6 (3)
C1—N1—C7—C6	−29.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1ⁱ	0.98	2.80	3.7337 (3)	159

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1ⁱ	0.981	2.803	3.7337 (3)	158.7

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 21271122 and 20901048) and Shanxi Scholarship Council of China (2013–018).

References

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

3,22-Dioxa-11,14-di­aza­penta­cyclo­[12.8.0.02,11.05,10.015,20]docosa-5(10),6,8,15(20),16,18-hexa­ene-4,21-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,22-Dioxa-11,14-diazapentacyclo[12.8.0.0^2,11.0^5,10.0^15,20]docosa-5(10),6,8,15(20),16,18-hexaene-4,21-dione