10,11,12,13-Tetrahydro-4,5,9,14-tetra­azadibenz[a,c]anthracene–benzene-1,4-dicarboxylic acid (2/1)

Liu, C.-B.; Wang, J.; Li, X.-Y.; Che, G.-B.; Liu, Y.

doi:10.1107/S1600536808027785

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1877

doi:10.1107/S1600536808027785

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10,11,12,13-Tetrahydro-4,5,9,14-tetraazadibenz[a,c]anthracene–benzene-1,4-dicarboxylic acid (2/1)

Chun-Bo Liu,^a Jian Wang,^a Xiu-Ying Li,^a Guang-Bo Che ^a ^* and Yang Liu ^a

^aDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
^*Correspondence e-mail: guangbochejl@yahoo.com

(Received 29 August 2008; accepted 29 August 2008; online 6 September 2008)

In the title adduct, 2C₁₈H₁₄N₄·C₈H₆O₄, the centrosymmetric 1,4-benzenedicarboxylic acid molecule makes two O—H⋯·N hydrogen bonds to adjacent 10,11,12,13-tetrahydro-4,5,9,14-tetraazadibenzo[a,c]anthracene (TTBT) molecules. Aromatic π–π stacking interactions occur between TTBT rings [centroid–centroid distance = 3.570 (3) Å], leading to a two-dimensional supramolecular structure in the crystal.

Related literature

For related literature, see: Che et al. (2006 , 2008 ); Stephenson & Hardie (2006 ); Xu et al. (2008 ); Yao et al. (2008 ).

Experimental

Crystal data

2C₁₈H₁₄N₄·C₈H₆O₄
M_r = 738.80
Triclinic, $[P \overline 1]$
a = 7.266 (4) Å
b = 9.917 (5) Å
c = 13.564 (9) Å
α = 101.469 (9)°
β = 97.429 (9)°
γ = 109.697 (6)°
V = 881.2 (9) Å³
Z = 1
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 (2) K
0.32 × 0.21 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.978, T_max = 0.992
7636 measured reflections
3444 independent reflections
1394 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.180
S = 0.93
3444 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2	0.82	2.02	2.694 (4)	139

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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 global, I. DOI: 10.1107/S1600536808027785/hb2788sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027785/hb2788Isup2.hkl

checkCIF report

Comment top

Current crystal engineering on the basis of the supramolecular architectures assembled from various noncovalent interactions, such as hydrogen bonds and π-π stacking interactions have been extensively studied owing to their novel topologies and potential applications as functional materials (Stephenson & Hardie, 2006; Yao et al.,2008). 1,10-Phenanthroline (phen) and its derivatives have been widely used to build novel supramolecular architectures (Xu, Li et al., 2008; Che, Liu et al., 2008). As a continuation of our studies in this area, we have prepared the title compound, (I), using the phen derivative 10,11,12,13-tetrahydro-4,5,9,14-tetraazadibenz[a,c]anthracene (TTBA).

The asymmetric unit of (I) consists of one TTBA molecule and half of a centrosymmetric 1,4-benzenedicarboxylic acid molecule (Fig. 1). The two components of (I) interact by way of O—H···N hydrogen bonds (Table 1). Furthermore, there are π-π aromatic stacking interactions involving TTBA ligands of adjacent units [centroid-centroid distance = 3.570 (3)Å], forming an intriguing two-dimensional supramolecular motif (Fig. 2).

Related literature top

For related literature, see: Che et al. (2006, 2008); Stephenson & Hardie (2006); Xu et al. (2008); Yao et al. (2008).

Experimental top

The TTBA was synthesized according to the literature method (Che, Li et al., 2006). TTBA (1.0 mmol) and 1,4-benzenedicarboxylic acid (0.5 mmol) were dissolved in aqueous solution and the mixture was sealed in a Teflon-lined autoclave and heated to 433 K for 4 d. Upon cooling and opening the bomb, colorless blocks of (I) were obtained.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. View of the molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for the H atoms). [Symmetry code: (i) 1 - x, -y, 3 - z.]
	Fig. 2. Packing diagram of the two-dimensional supramolecular structure of (I) formed via π–π interactions and hydrogen bonds. H atoms have been omitted.

10,11,12,13-Tetrahydro-4,5,9,14-tetraazadibenz[a,c]anthracene– benzene-1,4-dicarboxylic acid (2/1) top

Crystal data top

2C₁₈H₁₄N₄·C₈H₆O₄	Z = 1
M_r = 738.80	F(000) = 386
Triclinic, P1	D_x = 1.392 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.266 (4) Å	Cell parameters from 2386 reflections
b = 9.917 (5) Å	θ = 2.3–26.0°
c = 13.564 (9) Å	µ = 0.09 mm⁻¹
α = 101.469 (9)°	T = 292 K
β = 97.429 (9)°	Block, colorless
γ = 109.697 (6)°	0.32 × 0.21 × 0.08 mm
V = 881.2 (9) Å³

Data collection top

Bruker SMART CCD diffractometer	3444 independent reflections
Radiation source: fine-focus sealed tube	1394 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 26.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
T_min = 0.978, T_max = 0.992	k = −12→12
7636 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0762P)²] where P = (F_o² + 2F_c²)/3
3444 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

2C₁₈H₁₄N₄·C₈H₆O₄	γ = 109.697 (6)°
M_r = 738.80	V = 881.2 (9) Å³
Triclinic, P1	Z = 1
a = 7.266 (4) Å	Mo Kα radiation
b = 9.917 (5) Å	µ = 0.09 mm⁻¹
c = 13.564 (9) Å	T = 292 K
α = 101.469 (9)°	0.32 × 0.21 × 0.08 mm
β = 97.429 (9)°

Data collection top

Bruker SMART CCD diffractometer	3444 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1394 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.992	R_int = 0.047
7636 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 0.93	Δρ_max = 0.34 e Å⁻³
3444 reflections	Δρ_min = −0.18 e Å⁻³
253 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	0.7589 (5)	0.5815 (4)	1.2595 (3)	0.0603 (10)
H1	0.7594	0.6000	1.3295	0.072*
C2	0.7631 (5)	0.6947 (4)	1.2121 (3)	0.0593 (9)
H2	0.7692	0.7861	1.2495	0.071*
C3	0.7581 (4)	0.6668 (4)	1.1082 (3)	0.0534 (9)
H3	0.7589	0.7394	1.0739	0.064*
C4	0.7517 (4)	0.5297 (3)	1.0542 (2)	0.0411 (8)
C5	0.7492 (4)	0.4942 (3)	0.9448 (2)	0.0418 (8)
C6	0.7476 (4)	0.5624 (4)	0.7934 (3)	0.0473 (8)
C7	0.7508 (5)	0.6785 (4)	0.7365 (2)	0.0607 (10)
H7A	0.8810	0.7585	0.7590	0.073*
H7B	0.6518	0.7193	0.7543	0.073*
C8	0.7086 (6)	0.6201 (4)	0.6202 (3)	0.0773 (12)
H8A	0.5654	0.5694	0.5943	0.093*
H8B	0.7534	0.7030	0.5898	0.093*
C9	0.8103 (6)	0.5164 (4)	0.5882 (3)	0.0779 (12)
H9A	0.9537	0.5678	0.6125	0.093*
H9B	0.7826	0.4845	0.5137	0.093*
C10	0.7414 (6)	0.3822 (4)	0.6306 (2)	0.0669 (10)
H10A	0.6063	0.3186	0.5940	0.080*
H10B	0.8271	0.3265	0.6187	0.080*
C11	0.7453 (4)	0.4230 (4)	0.7430 (2)	0.0485 (8)
C12	0.7473 (4)	0.3561 (3)	0.8947 (2)	0.0433 (8)
C13	0.7493 (4)	0.2468 (3)	0.9524 (2)	0.0439 (8)
C14	0.7547 (4)	0.1100 (4)	0.9065 (3)	0.0535 (9)
H14	0.7545	0.0847	0.8367	0.064*
C15	0.7602 (5)	0.0130 (4)	0.9645 (3)	0.0578 (9)
H15	0.7664	−0.0782	0.9355	0.069*
C16	0.7563 (5)	0.0539 (4)	1.0681 (3)	0.0622 (10)
H16	0.7582	−0.0131	1.1071	0.075*
C17	0.7489 (4)	0.2799 (3)	1.0574 (2)	0.0431 (8)
C18	0.7504 (4)	0.4245 (3)	1.1102 (2)	0.0429 (8)
C19	0.7010 (6)	0.0878 (4)	1.3406 (3)	0.0611 (10)
C20	0.5949 (5)	0.0433 (3)	1.4226 (2)	0.0527 (9)
C21	0.4077 (6)	0.0460 (4)	1.4252 (3)	0.0597 (10)
H21	0.3439	0.0761	1.3747	0.072*
C22	0.6860 (5)	−0.0042 (4)	1.4971 (3)	0.0611 (10)
H22	0.8116	−0.0082	1.4950	0.073*
N1	0.7543 (4)	0.4499 (3)	1.2122 (2)	0.0533 (7)
N2	0.7502 (4)	0.1824 (3)	1.1147 (2)	0.0513 (7)
N3	0.7496 (4)	0.5981 (3)	0.89318 (19)	0.0472 (7)
N4	0.7442 (4)	0.3203 (3)	0.79299 (19)	0.0491 (7)
O1	0.8422 (4)	0.0570 (3)	1.3217 (2)	0.0853 (9)
O2	0.6271 (4)	0.1674 (3)	1.29255 (18)	0.0766 (8)
H2A	0.6112	0.1355	1.2302	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.067 (2)	0.068 (3)	0.049 (2)	0.028 (2)	0.0207 (18)	0.014 (2)
C2	0.070 (2)	0.053 (2)	0.057 (3)	0.0253 (19)	0.0208 (19)	0.0101 (19)
C3	0.054 (2)	0.053 (2)	0.058 (2)	0.0230 (18)	0.0178 (18)	0.0190 (19)
C4	0.0385 (18)	0.0422 (19)	0.043 (2)	0.0169 (15)	0.0081 (15)	0.0082 (16)
C5	0.0338 (18)	0.046 (2)	0.045 (2)	0.0133 (15)	0.0059 (15)	0.0148 (17)
C6	0.0439 (19)	0.050 (2)	0.049 (2)	0.0188 (17)	0.0066 (16)	0.0151 (18)
C7	0.069 (2)	0.065 (2)	0.051 (2)	0.0243 (19)	0.0119 (19)	0.0243 (19)
C8	0.106 (3)	0.082 (3)	0.053 (3)	0.043 (3)	0.015 (2)	0.026 (2)
C9	0.100 (3)	0.093 (3)	0.057 (2)	0.047 (3)	0.025 (2)	0.029 (2)
C10	0.084 (3)	0.070 (3)	0.043 (2)	0.027 (2)	0.0104 (19)	0.0135 (19)
C11	0.049 (2)	0.052 (2)	0.041 (2)	0.0161 (17)	0.0074 (16)	0.0106 (18)
C12	0.0388 (18)	0.047 (2)	0.042 (2)	0.0156 (15)	0.0067 (15)	0.0103 (17)
C13	0.0391 (18)	0.044 (2)	0.048 (2)	0.0137 (15)	0.0108 (15)	0.0134 (17)
C14	0.058 (2)	0.050 (2)	0.052 (2)	0.0230 (18)	0.0093 (17)	0.0091 (19)
C15	0.070 (2)	0.043 (2)	0.064 (2)	0.0256 (19)	0.0160 (19)	0.0128 (19)
C16	0.072 (2)	0.049 (2)	0.067 (3)	0.0211 (19)	0.015 (2)	0.023 (2)
C17	0.0412 (18)	0.0398 (19)	0.049 (2)	0.0132 (15)	0.0120 (15)	0.0146 (17)
C18	0.0401 (18)	0.048 (2)	0.043 (2)	0.0173 (16)	0.0116 (15)	0.0135 (17)
C19	0.079 (3)	0.053 (2)	0.057 (2)	0.025 (2)	0.024 (2)	0.0211 (19)
C20	0.067 (2)	0.043 (2)	0.050 (2)	0.0207 (18)	0.0185 (18)	0.0124 (17)
C21	0.074 (3)	0.059 (2)	0.054 (2)	0.030 (2)	0.0161 (19)	0.0227 (19)
C22	0.069 (2)	0.060 (2)	0.066 (2)	0.0287 (19)	0.023 (2)	0.025 (2)
N1	0.0634 (18)	0.0523 (19)	0.0464 (18)	0.0224 (15)	0.0166 (14)	0.0131 (15)
N2	0.0600 (18)	0.0427 (17)	0.0547 (18)	0.0202 (14)	0.0139 (14)	0.0171 (15)
N3	0.0502 (16)	0.0494 (17)	0.0433 (17)	0.0193 (13)	0.0087 (13)	0.0143 (14)
N4	0.0541 (17)	0.0485 (17)	0.0435 (18)	0.0194 (14)	0.0095 (13)	0.0098 (14)
O1	0.099 (2)	0.097 (2)	0.101 (2)	0.0578 (18)	0.0578 (18)	0.0550 (17)
O2	0.101 (2)	0.0836 (19)	0.0687 (17)	0.0465 (16)	0.0330 (15)	0.0399 (15)

Geometric parameters (Å, º) top

C1—N1	1.323 (4)	C10—H10B	0.9700
C1—C2	1.393 (4)	C11—N4	1.329 (4)
C1—H1	0.9300	C12—N4	1.349 (4)
C2—C3	1.375 (4)	C12—C13	1.461 (4)
C2—H2	0.9300	C13—C14	1.392 (4)
C3—C4	1.393 (4)	C13—C17	1.397 (4)
C3—H3	0.9300	C14—C15	1.366 (4)
C4—C18	1.405 (4)	C14—H14	0.9300
C4—C5	1.452 (4)	C15—C16	1.389 (4)
C5—N3	1.355 (3)	C15—H15	0.9300
C5—C12	1.398 (4)	C16—N2	1.322 (4)
C6—N3	1.327 (4)	C16—H16	0.9300
C6—C11	1.408 (4)	C17—N2	1.357 (4)
C6—C7	1.504 (4)	C17—C18	1.466 (4)
C7—C8	1.520 (4)	C18—N1	1.351 (4)
C7—H7A	0.9700	C19—O1	1.208 (4)
C7—H7B	0.9700	C19—O2	1.317 (4)
C8—C9	1.486 (5)	C19—C20	1.488 (5)
C8—H8A	0.9700	C20—C21	1.375 (4)
C8—H8B	0.9700	C20—C22	1.381 (4)
C9—C10	1.511 (4)	C21—C22ⁱ	1.384 (4)
C9—H9A	0.9700	C21—H21	0.9300
C9—H9B	0.9700	C22—C21ⁱ	1.384 (4)
C10—C11	1.491 (4)	C22—H22	0.9300
C10—H10A	0.9700	O2—H2A	0.8200

N1—C1—C2	124.8 (3)	N4—C11—C6	121.7 (3)
N1—C1—H1	117.6	N4—C11—C10	116.5 (3)
C2—C1—H1	117.6	C6—C11—C10	121.8 (3)
C3—C2—C1	117.8 (3)	N4—C12—C5	121.5 (3)
C3—C2—H2	121.1	N4—C12—C13	118.5 (3)
C1—C2—H2	121.1	C5—C12—C13	120.1 (3)
C2—C3—C4	119.9 (3)	C14—C13—C17	118.3 (3)
C2—C3—H3	120.1	C14—C13—C12	122.0 (3)
C4—C3—H3	120.1	C17—C13—C12	119.7 (3)
C3—C4—C18	117.4 (3)	C15—C14—C13	119.6 (3)
C3—C4—C5	122.5 (3)	C15—C14—H14	120.2
C18—C4—C5	120.1 (3)	C13—C14—H14	120.2
N3—C5—C12	121.2 (3)	C14—C15—C16	118.3 (3)
N3—C5—C4	118.5 (3)	C14—C15—H15	120.8
C12—C5—C4	120.3 (3)	C16—C15—H15	120.8
N3—C6—C11	121.7 (3)	N2—C16—C15	124.0 (3)
N3—C6—C7	116.9 (3)	N2—C16—H16	118.0
C11—C6—C7	121.4 (3)	C15—C16—H16	118.0
C6—C7—C8	113.5 (3)	N2—C17—C13	122.2 (3)
C6—C7—H7A	108.9	N2—C17—C18	117.4 (3)
C8—C7—H7A	108.9	C13—C17—C18	120.4 (3)
C6—C7—H7B	108.9	N1—C18—C4	123.4 (3)
C8—C7—H7B	108.9	N1—C18—C17	117.1 (3)
H7A—C7—H7B	107.7	C4—C18—C17	119.4 (3)
C9—C8—C7	112.1 (3)	O1—C19—O2	123.7 (4)
C9—C8—H8A	109.2	O1—C19—C20	123.6 (4)
C7—C8—H8A	109.2	O2—C19—C20	112.6 (4)
C9—C8—H8B	109.2	C21—C20—C22	119.2 (3)
C7—C8—H8B	109.2	C21—C20—C19	121.8 (3)
H8A—C8—H8B	107.9	C22—C20—C19	119.0 (4)
C8—C9—C10	111.6 (3)	C20—C21—C22ⁱ	120.1 (3)
C8—C9—H9A	109.3	C20—C21—H21	119.9
C10—C9—H9A	109.3	C22ⁱ—C21—H21	119.9
C8—C9—H9B	109.3	C20—C22—C21ⁱ	120.6 (3)
C10—C9—H9B	109.3	C20—C22—H22	119.7
H9A—C9—H9B	108.0	C21ⁱ—C22—H22	119.7
C11—C10—C9	112.4 (3)	C1—N1—C18	116.7 (3)
C11—C10—H10A	109.1	C16—N2—C17	117.6 (3)
C9—C10—H10A	109.1	C6—N3—C5	117.0 (3)
C11—C10—H10B	109.1	C11—N4—C12	116.9 (3)
C9—C10—H10B	109.1	C19—O2—H2A	109.5
H10A—C10—H10B	107.9

Symmetry code: (i) −x+1, −y, −z+3.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82	2.02	2.694 (4)	139

Experimental details

Crystal data
Chemical formula	2C₁₈H₁₄N₄·C₈H₆O₄
M_r	738.80
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	7.266 (4), 9.917 (5), 13.564 (9)
α, β, γ (°)	101.469 (9), 97.429 (9), 109.697 (6)
V (Å³)	881.2 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.21 × 0.08

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.978, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	7636, 3444, 1394
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.180, 0.93
No. of reflections	3444
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
O2—H2A···N2	0.82	2.02	2.694 (4)	139

Acknowledgements

The authors thank the Doctoral Foundation of Jilin Normal University (Nos. 2006006 and 2007009), the Subject and Base Construction Foundation of Jilin Normal University (No. 2006041) and the Masters' Innovation Foundation of Jilin Normal University (No. 2006064).

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Che, G.-B., Li, W.-L., Kong, Z.-G., Su, Z.-S., Chu, B., Li, B., Zhang, Z.-Q., Hu, Z.-Z. & Chi, H.-J. (2006). Synth. Commun. 36, 2519–2524. Web of Science CrossRef CAS Google Scholar
Che, G.-B., Liu, C.-B., Liu, B., Wang, Q.-W. & Xu, Z.-L. (2008). CrystEngComm, 10, 184–191. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 64| Part 10| October 2008| Page o1877

doi:10.1107/S1600536808027785

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

10,11,12,13-Tetra­hydro-4,5,9,14-tetra­azadibenz[a,c]anthracene–benzene-1,4-di­carboxylic acid (2/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

10,11,12,13-Tetrahydro-4,5,9,14-tetraazadibenz[a,c]anthracene–benzene-1,4-dicarboxylic acid (2/1)