4,5-Dicarb­oxy­naphthalene-1,8-dicarb­oxy­lic anhydride–1,10-phenanthroline (1/1)

Wu, X.-Y.; Xu, X.-J.; Wang, X.-C.

doi:10.1107/S1600536811002492

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o474

doi:10.1107/S1600536811002492

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4,5-Dicarboxynaphthalene-1,8-dicarboxylic anhydride–1,10-phenanthroline (1/1)

Xiang-Yang Wu,^a ^* Xiang-Jun Xu ^a and Xiang-Cheng Wang ^b

^aSchool of the Environment, Jiangsu University, Zhenjiang 212013, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China
^*Correspondence e-mail: xxj507@126.com

(Received 20 October 2010; accepted 18 January 2011; online 22 January 2011)

In the crystal structure of the title 1:1 adduct, C₁₂H₈N₂·C₁₄H₆O₇, the carboxyl groups are involved in intermolecular O—H⋯O hydrogen bonds, which link the molecules into centrosymmetric dimers. These dimers are further linked by intermolecular O—H⋯N hydrogen bonds. C—H⋯O interactions also occur between the 1,10-phenanthroline (phen) and 4,5-dicarboxynaphthalene-1,8-dicarboxylic anhydride (H₂NTC) molecules. In addition, the crystal structure exhibits π–π interactions of the phen⋯phen and H₂NTC⋯H₂NTC types with centroid–centroid distances of 3.579 (3) and 3.774 (3) Å, respectively.

Related literature

For background to the importance of 1,4,5,8-naphthalenetetracarboxylic acid and 1,10-phenanthroline, see: Chen et al. (2005 ); Che et al. (2006 ).

Experimental

Crystal data

C₁₂H₈N₂·C₁₄H₆O₇
M_r = 466.39
Triclinic, $[P \overline 1]$
a = 9.0189 (5) Å
b = 10.1588 (7) Å
c = 11.2140 (8) Å
α = 104.267 (6)°
β = 92.278 (5)°
γ = 101.256 (5)°
V = 972.42 (11) Å³
Z = 2
Cu Kα radiation
μ = 0.99 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.858, T_max = 1.000
6756 measured reflections
3416 independent reflections
2679 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.159
S = 0.99
3416 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1ⁱ	0.82	1.97	2.683 (2)	144
O4—H4⋯O1ⁱⁱ	0.82	1.69	2.4637 (18)	158
C2—H2⋯O5ⁱⁱⁱ	0.93	2.59	3.481 (3)	161
C8—H8⋯O3ⁱⁱ	0.93	2.57	3.312 (3)	137
C10—H10⋯O4^iv	0.93	2.42	3.258 (3)	150
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+2; (iii) -x, -y+1, -z+1; (iv) -x, -y, -z+2.

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) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002492/lx2183sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002492/lx2183Isup2.hkl

checkCIF report

Comment top

1,4,5,8-Naphthalenetetracarboxylic acid (H₄NTC) is of special interest since its high symmetry and large π-conjugated structure can allow to construct molecular assemblies with novel structure motifs and physical properties (Chen et al., 2005). The 1,10-phenanthroline (phen) has been widely used to build novel supramolecular architectures through aromatic π..π interactions (Che et al., 2006). We report herein on the crystal structure of the title compound (Fig. 1).

In the crystal packing (Fig. 2), the carboxyl groups are involved in intermolecular O–H···O hydrogen bonds, which link the molecules into centrosymmetric dimers. These dimers are further linked by an intermolecular O–H···N hydrogen bond. There are also C–H···O interactions between the phen and H₂NTC (Table 1). In addition, the crystal structure exhibit the π-π interactions between the phen···phen and H₂NTC···H₂NTC, respectively. The π-π interaction distance (Cg1-to-Cg2ⁱ) between the phen···phen is 3.579 (3) Å, and the π-π interaction distance (Cg3-to-Cg4ⁱⁱ) between the H₂NTC···H₂NTC is 3.774 (3) Å (Fig. 3). Cg1, Cg2, Cg3 and Cg4 are centroids of the N2-C2, N1-C7, C18-C20 and C13-C15 ring, respectively.

Related literature top

For background to the importance of 1,4,5,8-naphthalenetetracarboxylic acid and 1,10-phenanthroline, see: Chen et al. (2005); Che et al. (2006).

Experimental top

The reagents, purchased from standard commercial sources and without further purification, were 1,4,5,8-naphthalenetetracarboxylic acid and 1,10-phenanthroline. A mixture of H₄NTC (0.0304 g, 0.10 mmol), phen (0.018 g, 0.10 mmol) and water (10 mL) in a 25 mL Teflon-lined stainless steel autoclave was heated for 3 d at 433 K under autogenous pressure and cooled to room temperature. Yellow block crystals 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) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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 a small spheres of arbitrary radius.
	Fig. 2. A view of the hydrogen bond and C–H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x + 1, y, z; (ii) - x + 1, - y, - z + 2; (iii) - x, - y + 1, - z + 1; (iv) - x, - y, - z + 2; (v) x - 1, y, z.]
	Fig. 3. A view of π-π interactions (dotted lines) in the unit cell of the title compound. [Symmetry codes: (i) - x, - y, - z + 1; (ii) -x + 1, - y + 1, - z + 2.]

4,5-Dicarboxynaphthalene-1,8-dicarboxylic anhydride–1,10-phenanthroline (1/1) top

Crystal data top

C₁₂H₈N₂·C₁₄H₆O₇	Z = 2
M_r = 466.39	F(000) = 480
Triclinic, P1	D_x = 1.593 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.0189 (5) Å	Cell parameters from 3294 reflections
b = 10.1588 (7) Å	θ = 4.1–67.0°
c = 11.2140 (8) Å	µ = 0.99 mm⁻¹
α = 104.267 (6)°	T = 293 K
β = 92.278 (5)°	Block, yellow
γ = 101.256 (5)°	0.35 × 0.25 × 0.2 mm
V = 972.42 (11) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3416 independent reflections
Radiation source: fine-focus sealed tube	2679 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 67.1°, θ_min = 4.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→10
T_min = 0.858, T_max = 1.000	k = −12→12
6756 measured reflections	l = −13→13

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)] = 0.056	Hydrogen site location: difference Fourier map
wR(F²) = 0.159	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.1188P)²] where P = (F_o² + 2F_c²)/3
3416 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₂H₈N₂·C₁₄H₆O₇	γ = 101.256 (5)°
M_r = 466.39	V = 972.42 (11) Å³
Triclinic, P1	Z = 2
a = 9.0189 (5) Å	Cu Kα radiation
b = 10.1588 (7) Å	µ = 0.99 mm⁻¹
c = 11.2140 (8) Å	T = 293 K
α = 104.267 (6)°	0.35 × 0.25 × 0.2 mm
β = 92.278 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3416 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2679 reflections with I > 2σ(I)
T_min = 0.858, T_max = 1.000	R_int = 0.061
6756 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 0.99	Δρ_max = 0.49 e Å⁻³
3416 reflections	Δρ_min = −0.41 e Å⁻³
316 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.55753 (16)	0.06531 (14)	0.84023 (14)	0.0425 (4)
O2	0.79210 (15)	0.19823 (17)	0.87789 (16)	0.0469 (4)
H2A	0.8273	0.1546	0.8181	0.070*
O3	0.57213 (15)	0.23703 (14)	1.08928 (14)	0.0399 (4)
O4	0.33967 (16)	0.10420 (17)	1.07563 (16)	0.0471 (4)
H4	0.3822	0.0657	1.1189	0.071*
O5	0.04091 (17)	0.56071 (18)	0.81155 (17)	0.0538 (5)
O6	0.23485 (16)	0.57884 (15)	0.70001 (13)	0.0415 (4)
O7	0.4382 (2)	0.6322 (2)	0.60562 (17)	0.0583 (5)
N1	−0.00536 (18)	0.06070 (18)	0.76513 (16)	0.0364 (4)
N2	−0.0387 (2)	0.2209 (2)	0.60381 (17)	0.0437 (4)
C1	−0.0510 (3)	0.2947 (3)	0.5239 (2)	0.0510 (6)
H1	−0.1358	0.3342	0.5238	0.061*
C2	0.0537 (3)	0.3179 (2)	0.4397 (2)	0.0512 (6)
H2	0.0392	0.3718	0.3859	0.061*
C3	0.1778 (3)	0.2602 (3)	0.4375 (2)	0.0498 (6)
H3	0.2494	0.2740	0.3819	0.060*
C4	0.1968 (2)	0.1796 (2)	0.5201 (2)	0.0421 (5)
C5	0.3233 (3)	0.1145 (3)	0.5236 (3)	0.0587 (7)
H5	0.3993	0.1286	0.4717	0.070*
C6	0.3346 (3)	0.0337 (3)	0.6003 (3)	0.0567 (7)
H6	0.4176	−0.0082	0.5995	0.068*
C7	0.2219 (2)	0.0106 (2)	0.6831 (2)	0.0385 (5)
C8	0.2284 (2)	−0.0737 (2)	0.7640 (2)	0.0422 (5)
H8	0.3086	−0.1189	0.7647	0.051*
C9	0.1178 (2)	−0.0901 (2)	0.8420 (2)	0.0405 (5)
H9	0.1211	−0.1472	0.8949	0.049*
C10	0.0006 (2)	−0.0202 (2)	0.84104 (19)	0.0395 (5)
H10	−0.0749	−0.0301	0.8942	0.047*
C11	0.1000 (2)	0.0779 (2)	0.68408 (18)	0.0325 (4)
C12	0.0848 (2)	0.1632 (2)	0.60101 (18)	0.0348 (4)
C13	0.2358 (2)	0.44630 (19)	0.85406 (18)	0.0314 (4)
C14	0.1623 (2)	0.3913 (2)	0.9408 (2)	0.0375 (5)
H14	0.0672	0.4080	0.9601	0.045*
C15	0.2311 (2)	0.3098 (2)	1.00005 (19)	0.0361 (4)
H15	0.1822	0.2756	1.0611	0.043*
C16	0.3691 (2)	0.27875 (19)	0.97076 (17)	0.0303 (4)
C25	0.4381 (2)	0.20230 (19)	1.05024 (17)	0.0316 (4)
C26	0.6530 (2)	0.1802 (2)	0.85624 (19)	0.0350 (4)
C17	0.4462 (2)	0.32898 (18)	0.87661 (17)	0.0282 (4)
C18	0.5859 (2)	0.2975 (2)	0.83327 (18)	0.0330 (4)
C19	0.6576 (2)	0.3638 (2)	0.7515 (2)	0.0417 (5)
H19	0.7522	0.3482	0.7293	0.050*
C20	0.5921 (2)	0.4540 (2)	0.7011 (2)	0.0419 (5)
H20	0.6428	0.4974	0.6459	0.050*
C21	0.4528 (2)	0.4785 (2)	0.73298 (18)	0.0338 (4)
C22	0.3780 (2)	0.41784 (18)	0.82119 (17)	0.0289 (4)
C23	0.3816 (2)	0.5682 (2)	0.67520 (19)	0.0389 (5)
C24	0.1622 (2)	0.5316 (2)	0.79219 (19)	0.0371 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0442 (8)	0.0336 (8)	0.0555 (9)	0.0109 (6)	−0.0002 (7)	0.0212 (7)
O2	0.0352 (8)	0.0528 (9)	0.0640 (10)	0.0208 (7)	0.0146 (7)	0.0256 (8)
O3	0.0383 (8)	0.0401 (8)	0.0454 (8)	0.0087 (6)	−0.0018 (6)	0.0190 (6)
O4	0.0385 (8)	0.0480 (9)	0.0698 (10)	0.0107 (7)	0.0066 (7)	0.0417 (8)
O5	0.0447 (9)	0.0638 (11)	0.0712 (11)	0.0291 (8)	0.0095 (8)	0.0372 (9)
O6	0.0459 (8)	0.0451 (8)	0.0428 (8)	0.0162 (6)	0.0012 (6)	0.0240 (7)
O7	0.0721 (11)	0.0672 (11)	0.0600 (11)	0.0310 (9)	0.0226 (9)	0.0462 (9)
N1	0.0358 (9)	0.0413 (9)	0.0357 (9)	0.0130 (7)	0.0040 (7)	0.0128 (7)
N2	0.0476 (10)	0.0500 (11)	0.0421 (10)	0.0231 (8)	0.0037 (8)	0.0177 (8)
C1	0.0599 (14)	0.0536 (14)	0.0475 (13)	0.0245 (11)	−0.0022 (11)	0.0190 (11)
C2	0.0679 (15)	0.0445 (12)	0.0453 (12)	0.0111 (11)	−0.0047 (11)	0.0214 (10)
C3	0.0553 (14)	0.0497 (13)	0.0477 (13)	0.0050 (11)	0.0045 (10)	0.0240 (11)
C4	0.0403 (11)	0.0440 (12)	0.0455 (12)	0.0088 (9)	0.0037 (9)	0.0180 (10)
C5	0.0470 (13)	0.0779 (18)	0.0676 (16)	0.0252 (12)	0.0226 (12)	0.0373 (14)
C6	0.0441 (12)	0.0761 (17)	0.0690 (16)	0.0325 (12)	0.0222 (11)	0.0359 (14)
C7	0.0340 (10)	0.0409 (11)	0.0440 (11)	0.0122 (8)	0.0036 (8)	0.0140 (9)
C8	0.0400 (11)	0.0407 (11)	0.0508 (12)	0.0163 (9)	0.0001 (9)	0.0158 (10)
C9	0.0468 (11)	0.0366 (11)	0.0409 (11)	0.0098 (9)	0.0003 (9)	0.0150 (9)
C10	0.0431 (11)	0.0430 (11)	0.0377 (10)	0.0129 (9)	0.0061 (8)	0.0172 (9)
C11	0.0312 (9)	0.0335 (10)	0.0340 (10)	0.0093 (8)	0.0009 (7)	0.0096 (8)
C12	0.0369 (10)	0.0350 (10)	0.0338 (10)	0.0095 (8)	−0.0013 (8)	0.0104 (8)
C13	0.0324 (9)	0.0296 (9)	0.0365 (10)	0.0104 (7)	0.0018 (8)	0.0133 (8)
C14	0.0357 (10)	0.0390 (11)	0.0463 (11)	0.0155 (9)	0.0108 (9)	0.0199 (9)
C15	0.0380 (10)	0.0357 (10)	0.0425 (11)	0.0129 (8)	0.0117 (8)	0.0199 (9)
C16	0.0321 (9)	0.0280 (9)	0.0344 (10)	0.0089 (7)	0.0033 (8)	0.0129 (8)
C25	0.0346 (10)	0.0303 (9)	0.0345 (10)	0.0104 (8)	0.0055 (8)	0.0136 (8)
C26	0.0353 (10)	0.0377 (11)	0.0399 (10)	0.0141 (8)	0.0104 (8)	0.0187 (9)
C17	0.0281 (9)	0.0258 (8)	0.0342 (9)	0.0072 (7)	0.0029 (7)	0.0133 (7)
C18	0.0333 (10)	0.0310 (10)	0.0405 (10)	0.0095 (8)	0.0067 (8)	0.0173 (8)
C19	0.0371 (10)	0.0446 (12)	0.0554 (13)	0.0162 (9)	0.0179 (9)	0.0272 (10)
C20	0.0463 (12)	0.0412 (11)	0.0493 (12)	0.0142 (9)	0.0178 (9)	0.0264 (10)
C21	0.0403 (10)	0.0323 (10)	0.0337 (10)	0.0102 (8)	0.0063 (8)	0.0152 (8)
C22	0.0322 (9)	0.0264 (9)	0.0303 (9)	0.0071 (7)	0.0016 (7)	0.0110 (7)
C23	0.0474 (12)	0.0385 (11)	0.0378 (11)	0.0144 (9)	0.0071 (9)	0.0185 (9)
C24	0.0388 (10)	0.0352 (10)	0.0415 (11)	0.0111 (8)	0.0007 (8)	0.0152 (9)

Geometric parameters (Å, º) top

O1—C26	1.276 (2)	C7—C11	1.403 (3)
O2—C26	1.237 (2)	C8—C9	1.365 (3)
O2—H2A	0.8200	C8—H8	0.9300
O3—C25	1.222 (2)	C9—C10	1.384 (3)
O4—C25	1.295 (2)	C9—H9	0.9300
O4—H4	0.8200	C10—H10	0.9300
O5—C24	1.202 (3)	C11—C12	1.439 (3)
O6—C24	1.380 (3)	C13—C14	1.369 (3)
O6—C23	1.382 (3)	C13—C22	1.412 (3)
O7—C23	1.201 (3)	C13—C24	1.469 (3)
N1—C10	1.327 (3)	C14—C15	1.396 (3)
N1—C11	1.357 (3)	C14—H14	0.9300
N2—C1	1.317 (3)	C15—C16	1.376 (3)
N2—C12	1.354 (3)	C15—H15	0.9300
C1—C2	1.391 (4)	C16—C17	1.430 (3)
C1—H1	0.9300	C16—C25	1.507 (2)
C2—C3	1.359 (4)	C26—C18	1.508 (3)
C2—H2	0.9300	C17—C22	1.429 (2)
C3—C4	1.405 (3)	C17—C18	1.434 (3)
C3—H3	0.9300	C18—C19	1.376 (3)
C4—C12	1.398 (3)	C19—C20	1.396 (3)
C4—C5	1.429 (3)	C19—H19	0.9300
C5—C6	1.341 (3)	C20—C21	1.372 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.428 (3)	C21—C22	1.416 (3)
C6—H6	0.9300	C21—C23	1.466 (3)
C7—C8	1.399 (3)

C26—O2—H2A	109.5	C14—C13—C24	119.01 (17)
C25—O4—H4	109.5	C22—C13—C24	120.29 (17)
C24—O6—C23	123.76 (15)	C13—C14—C15	119.51 (18)
C10—N1—C11	122.47 (17)	C13—C14—H14	120.2
C1—N2—C12	116.5 (2)	C15—C14—H14	120.2
N2—C1—C2	124.6 (2)	C16—C15—C14	121.89 (18)
N2—C1—H1	117.7	C16—C15—H15	119.1
C2—C1—H1	117.7	C14—C15—H15	119.1
C3—C2—C1	118.6 (2)	C15—C16—C17	120.23 (16)
C3—C2—H2	120.7	C15—C16—C25	116.49 (16)
C1—C2—H2	120.7	C17—C16—C25	123.04 (16)
C2—C3—C4	119.4 (2)	O3—C25—O4	125.51 (17)
C2—C3—H3	120.3	O3—C25—C16	121.47 (16)
C4—C3—H3	120.3	O4—C25—C16	112.93 (16)
C12—C4—C3	117.3 (2)	O2—C26—O1	125.89 (18)
C12—C4—C5	119.7 (2)	O2—C26—C18	119.39 (17)
C3—C4—C5	123.1 (2)	O1—C26—C18	114.43 (16)
C6—C5—C4	121.4 (2)	C22—C17—C16	117.17 (16)
C6—C5—H5	119.3	C22—C17—C18	117.40 (17)
C4—C5—H5	119.3	C16—C17—C18	125.43 (16)
C5—C6—C7	121.4 (2)	C19—C18—C17	120.01 (17)
C5—C6—H6	119.3	C19—C18—C26	114.89 (17)
C7—C6—H6	119.3	C17—C18—C26	124.54 (16)
C8—C7—C11	118.72 (19)	C18—C19—C20	121.70 (18)
C8—C7—C6	123.41 (19)	C18—C19—H19	119.2
C11—C7—C6	117.86 (19)	C20—C19—H19	119.2
C9—C8—C7	120.47 (19)	C21—C20—C19	119.95 (19)
C9—C8—H8	119.8	C21—C20—H20	120.0
C7—C8—H8	119.8	C19—C20—H20	120.0
C8—C9—C10	118.9 (2)	C20—C21—C22	120.37 (18)
C8—C9—H9	120.6	C20—C21—C23	119.60 (18)
C10—C9—H9	120.6	C22—C21—C23	120.03 (17)
N1—C10—C9	120.8 (2)	C13—C22—C21	119.40 (16)
N1—C10—H10	119.6	C13—C22—C17	120.38 (17)
C9—C10—H10	119.6	C21—C22—C17	120.23 (17)
N1—C11—C7	118.59 (18)	O7—C23—O6	116.28 (18)
N1—C11—C12	120.00 (17)	O7—C23—C21	125.9 (2)
C7—C11—C12	121.40 (18)	O6—C23—C21	117.81 (17)
N2—C12—C4	123.60 (19)	O5—C24—O6	116.34 (17)
N2—C12—C11	118.22 (18)	O5—C24—C13	125.90 (19)
C4—C12—C11	118.17 (18)	O6—C24—C13	117.71 (17)
C14—C13—C22	120.67 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1ⁱ	0.82	1.97	2.683 (2)	144
O4—H4···O1ⁱⁱ	0.82	1.69	2.4637 (18)	158
C2—H2···O5ⁱⁱⁱ	0.93	2.59	3.481 (3)	161
C8—H8···O3ⁱⁱ	0.93	2.57	3.312 (3)	137
C10—H10···O4^iv	0.93	2.42	3.258 (3)	150

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+2; (iii) −x, −y+1, −z+1; (iv) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₂H₈N₂·C₁₄H₆O₇
M_r	466.39
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.0189 (5), 10.1588 (7), 11.2140 (8)
α, β, γ (°)	104.267 (6), 92.278 (5), 101.256 (5)
V (Å³)	972.42 (11)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.35 × 0.25 × 0.2

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.858, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6756, 3416, 2679
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.159, 0.99
No. of reflections	3416
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.41

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1ⁱ	0.82	1.97	2.683 (2)	144
O4—H4···O1ⁱⁱ	0.82	1.69	2.4637 (18)	158
C2—H2···O5ⁱⁱⁱ	0.93	2.59	3.481 (3)	161
C8—H8···O3ⁱⁱ	0.93	2.57	3.312 (3)	137
C10—H10···O4^iv	0.93	2.42	3.258 (3)	150

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+2; (iii) −x, −y+1, −z+1; (iv) −x, −y, −z+2.

Acknowledgements

The authors thank Jiangsu University for supporting this work.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Che, G.-B., Xu, Z.-L. & Liu, C.-B. (2006). Acta Cryst. E62, m1370–m1372. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chen, L.-F., Zhang, C., Song, L.-J. & Ju, Z.-F. (2005). Inorg. Chem. Commun. 8, 555–558. Web of Science 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 67| Part 2| February 2011| Page o474

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

4,5-Dicarb­­oxy­naphthalene-1,8-dicarb­­oxy­lic anhydride–1,10-phenanthroline (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,5-Dicarboxynaphthalene-1,8-dicarboxylic anhydride–1,10-phenanthroline (1/1)