Di-μ-glutarato-κ4O1:O5-bis­[aqua­(1,10-phenanthroline-κ2N,N′)copper(II)]

Zhou, Y.-H.

doi:10.1107/S1600536811007938

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m411

doi:10.1107/S1600536811007938

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Di-μ-glutarato-κ⁴O¹:O⁵-bis[aqua(1,10-phenanthroline-κ²N,N′)copper(II)]

Yong-Hong Zhou ^a ^*

^aSchool of Chemistry and Material Science, Huaibei Normal University, Huaibei 235000, People's Republic of China
^*Correspondence e-mail: zhou21921@sina.com

(Received 20 February 2011; accepted 2 March 2011; online 9 March 2011)

In the centrosymmetric dinuclear title complex, [Cu₂(C₅H₆O₄)₂(C₁₂H₁₈N₂)₂(H₂O)₂], the Cu^II atom displays a distorted square-pyramidal coordination environment with the basal plane occupied by two phenanthroline N atoms and two O atoms from different glutarate dianions while a water molecule is located at the apical position. Of the two water H atoms, one is engaged in an intramolecular hydrogen bond with a free oxygen of the dianion whereas the second is engaged in an intermolecular hydrogen bond, building a corrugated layer parallel to (100). These layers are further connected through π–π stacking interactions involving symmetry-related phenanthroline rings [centroid–centroid distance = 3.5599 (17) and 3.5617 (18) Å], building a three dimensionnal network. C—H⋯π interactions involving the phenanthroline ring system are also observed.

Related literature

For coordination modes of the glutarate anion, see: Ghosh et al. (2007 ); Kim et al. (2005 ); Rather & Zaworotko (2003 ); Zheng et al. (2004 ); Vaidhyanathan et al. (2004 ); Girginova et al. (2007 ).

Experimental

Crystal data

[Cu₂(C₅H₆O₄)₂(C₁₂H₁₈N₂)₂(H₂O)₂]
M_r = 783.72
Monoclinic, P 2₁ /c
a = 10.2767 (11) Å
b = 10.5935 (14) Å
c = 15.5998 (16) Å
β = 107.114 (1)°
V = 1623.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.38 mm⁻¹
T = 298 K
0.26 × 0.25 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.716, T_max = 0.742
7937 measured reflections
2867 independent reflections
2275 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.083
S = 1.07
2867 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C6–C10 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4	0.89	1.81	2.659 (3)	158
O5—H52⋯O2ⁱ	0.88	1.89	2.762 (3)	169
C2—H2A⋯Cg1ⁱ	0.97	2.88	3.754 (3)	151
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536811007938/dn2661sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007938/dn2661Isup2.hkl

checkCIF report

Comment top

For many yeras, there is a growing interest in developing organic-inorganic hybrid materials owing to their intriguing structures, new topologies, and potential applications(Ghosh et al., 2007; Kim et al.,2005). Carboxylic acids have been proved to be versatile functional moieties in generating interesting hybrid materials by interacting with metal ions. The abilities of its anion to metal ions in diverse and unique linking modes can be regarded as a major factor in making the carboxylate function a versatile structure directing moiety.

Metal glutarates are one class of dicarboxylate system which exhibit interesting structural features. Previous investigations have demonstrated that glutaric acid presents interesting behaviors due to its conformational flexibility and coordination diversity (Rather et al., 2003; Zheng et al., 2004; Vaidhyanathan et al., 2004; Girginova et al., 2007). We report here the crystal structure of the title compound.

The title complex, [Cu(C₁₂H₁₈N₂)(C₅H₆O₄)(H₂O)]₂, is a dinuclear compound organized around inversion center. The Cu^II displays a distorted square pyramidal coordination environment (Fig. 1). The basal plane is occupied by two nitrogen atoms of the phenanthroline [Cu—N(1) = 2.014 (2)Å and Cu—N(2) = 2.022 (2) Å] and two O atoms from different glutarate dianions[Cu—O(1) = 1.954 (2)Å and Cu—O(3) = 1.947 (2) Å], whereas one water molecule is located at the apical position at a significantly longer distance[Cu—O(5) = 2.380 (2) Å]. The glutarate dianions act as a bidentate ligand bridging the two Cu^II ions which are separated by 8.476 Å.

There is an intramolecular hydrogen bond involving one H of the water and the O4 oxygen of one dianion within the dinuclear complex. The second H atom of the water is engaged in hydrogen bond interaction with the O2 oxygen atom of symmetry related dinuclear complex building then a corrugated layer parallel to the (1 0 0) plane (Fig. 2, Table 1). The layers are interconnected through π-π stacking involving the symmetry related N1,C6,C7,C8,C9,C10 (A) and N2,C11,C12,C13,C14,C15 (B) phenanthroline rings (Fig. 2, Table 2) building a three dimensional network. The packing is further stabilized by weak C—H···π interaction involving the symmetry related ring A (Table 1).

Related literature top

For coordination modes of the glutarate anion, see: Ghosh et al. (2007); Kim et al. (2005); Rather et al. (2003); Zheng et al. (2004); Vaidhyanathan et al. (2004); Girginova et al. (2007). Scheme - waters should coordinate through O atoms

Experimental top

The title complex was prepared by the addition of the stoichiometric amount of CuCl₂ (0.134 g, 1 mmol) to an ethanol solution of glutaric acid (0.264 g, 2 mmol) and 1,10-phenanthroline monohydrate(0.396 g, 2 mmol), the pH was adjusted to ~6 with 0.2 mol.L^-1 KOH solution. The resulting solution was stirred for 30 min at room temperature and then filtered. Blue single crystals were isolated from the solution at room temperature over two weeks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom labeling scheme. Displacement thermal paremeters are represented at the 30% probability level. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for the sake of clarity. [Symmetry code: (i) -x + 1, -y + 1, -z + 1]
	Fig. 2. Partial packing view showing the formation of layer through O—H···O hydrogen bonds which are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for the sake of clarity.

Di-µ-glutarato-κ⁴O¹:O⁵-bis[aqua(1,10-phenanthroline-κ²N,N')copper(II)] top

Crystal data top

[Cu₂(C₅H₆O₄)₂(C₁₂H₁₈N₂)₂(H₂O)₂]	F(000) = 804
M_r = 783.72	D_x = 1.604 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3334 reflections
a = 10.2767 (11) Å	θ = 2.4–27.3°
b = 10.5935 (14) Å	µ = 1.38 mm⁻¹
c = 15.5998 (16) Å	T = 298 K
β = 107.114 (1)°	Block, blue
V = 1623.1 (3) Å³	0.26 × 0.25 × 0.23 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2867 independent reflections
Radiation source: fine-focus sealed tube	2275 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→12
T_min = 0.716, T_max = 0.742	k = −12→10
7937 measured reflections	l = −18→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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0346P)² + 1.103P] where P = (F_o² + 2F_c²)/3
2867 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Cu₂(C₅H₆O₄)₂(C₁₂H₁₈N₂)₂(H₂O)₂]	V = 1623.1 (3) Å³
M_r = 783.72	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2767 (11) Å	µ = 1.38 mm⁻¹
b = 10.5935 (14) Å	T = 298 K
c = 15.5998 (16) Å	0.26 × 0.25 × 0.23 mm
β = 107.114 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2867 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2275 reflections with I > 2σ(I)
T_min = 0.716, T_max = 0.742	R_int = 0.028
7937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.07	Δρ_max = 0.31 e Å⁻³
2867 reflections	Δρ_min = −0.28 e Å⁻³
226 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
Cu1	0.34382 (3)	0.54797 (3)	0.21857 (2)	0.03292 (13)
N1	0.2087 (2)	0.4429 (2)	0.12652 (14)	0.0299 (5)
N2	0.3977 (2)	0.6012 (2)	0.10928 (14)	0.0318 (5)
O1	0.5068 (2)	0.61750 (19)	0.30440 (12)	0.0416 (5)
O2	0.5850 (2)	0.43066 (19)	0.28151 (13)	0.0432 (5)
O3	0.2798 (2)	0.4813 (2)	0.31524 (13)	0.0467 (5)
O4	0.1462 (3)	0.6404 (2)	0.32731 (17)	0.0689 (7)
O5	0.2215 (2)	0.74242 (19)	0.19357 (13)	0.0441 (5)
H51	0.1900	0.7287	0.2401	0.066*
H52	0.2746	0.8093	0.2014	0.066*
C1	0.5979 (3)	0.5330 (3)	0.32214 (17)	0.0318 (6)
C2	0.7228 (3)	0.5601 (3)	0.39982 (18)	0.0397 (7)
H2A	0.7284	0.6499	0.4125	0.048*
H2B	0.8038	0.5354	0.3841	0.048*
C3	0.7158 (3)	0.4873 (3)	0.48313 (18)	0.0380 (7)
H3A	0.6265	0.4993	0.4910	0.046*
H3B	0.7266	0.3980	0.4735	0.046*
C4	0.1767 (3)	0.4723 (3)	0.43155 (18)	0.0401 (7)
H4A	0.1805	0.3816	0.4242	0.048*
H4B	0.0869	0.4938	0.4356	0.048*
C5	0.2012 (3)	0.5385 (3)	0.35137 (18)	0.0387 (7)
C6	0.1142 (3)	0.3640 (3)	0.13755 (19)	0.0370 (7)
H6	0.1091	0.3496	0.1953	0.044*
C7	0.0230 (3)	0.3025 (3)	0.0664 (2)	0.0417 (7)
H7	−0.0423	0.2487	0.0768	0.050*
C8	0.0291 (3)	0.3208 (3)	−0.0187 (2)	0.0401 (7)
H8	−0.0321	0.2800	−0.0667	0.048*
C9	0.1287 (3)	0.4017 (3)	−0.03337 (18)	0.0339 (6)
C10	0.2164 (3)	0.4611 (2)	0.04186 (17)	0.0292 (6)
C11	0.3172 (3)	0.5485 (2)	0.03226 (17)	0.0294 (6)
C12	0.3286 (3)	0.5760 (3)	−0.05311 (18)	0.0368 (7)
C13	0.4278 (3)	0.6647 (3)	−0.0576 (2)	0.0445 (8)
H13	0.4398	0.6864	−0.1126	0.053*
C14	0.5061 (3)	0.7183 (3)	0.0194 (2)	0.0472 (8)
H14	0.5717	0.7776	0.0171	0.057*
C15	0.4890 (3)	0.6853 (3)	0.1024 (2)	0.0397 (7)
H15	0.5435	0.7237	0.1542	0.048*
C16	0.1444 (3)	0.4307 (3)	−0.11997 (19)	0.0429 (8)
H16	0.0881	0.3915	−0.1707	0.051*
C17	0.2384 (3)	0.5131 (3)	−0.12896 (19)	0.0453 (8)
H17	0.2455	0.5299	−0.1859	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0360 (2)	0.0377 (2)	0.02556 (18)	0.00182 (16)	0.00982 (14)	−0.00183 (15)
N1	0.0338 (12)	0.0290 (12)	0.0281 (11)	0.0019 (10)	0.0112 (10)	0.0016 (9)
N2	0.0340 (13)	0.0280 (12)	0.0336 (12)	0.0029 (10)	0.0105 (10)	0.0010 (10)
O1	0.0444 (12)	0.0396 (12)	0.0349 (11)	0.0059 (10)	0.0024 (9)	−0.0066 (9)
O2	0.0467 (13)	0.0412 (12)	0.0381 (11)	0.0073 (10)	0.0072 (9)	−0.0055 (9)
O3	0.0591 (14)	0.0546 (14)	0.0325 (11)	0.0083 (11)	0.0230 (10)	0.0053 (10)
O4	0.095 (2)	0.0595 (16)	0.0710 (16)	0.0257 (15)	0.0535 (15)	0.0232 (14)
O5	0.0495 (12)	0.0443 (12)	0.0379 (11)	−0.0074 (10)	0.0120 (9)	−0.0047 (9)
C1	0.0351 (15)	0.0379 (17)	0.0232 (13)	−0.0013 (13)	0.0097 (11)	0.0041 (12)
C2	0.0365 (16)	0.0490 (18)	0.0310 (14)	−0.0073 (14)	0.0057 (12)	0.0045 (13)
C3	0.0428 (17)	0.0383 (17)	0.0316 (15)	−0.0051 (13)	0.0090 (13)	0.0043 (13)
C4	0.0410 (17)	0.0481 (19)	0.0319 (15)	−0.0069 (14)	0.0117 (13)	−0.0004 (13)
C5	0.0417 (17)	0.0492 (19)	0.0253 (14)	−0.0065 (15)	0.0100 (12)	−0.0020 (14)
C6	0.0390 (16)	0.0338 (16)	0.0417 (16)	0.0031 (13)	0.0174 (13)	0.0044 (13)
C7	0.0359 (16)	0.0317 (16)	0.0580 (19)	−0.0016 (13)	0.0147 (14)	−0.0013 (14)
C8	0.0325 (16)	0.0339 (16)	0.0475 (18)	0.0027 (13)	0.0019 (13)	−0.0101 (14)
C9	0.0342 (15)	0.0326 (15)	0.0313 (14)	0.0095 (12)	0.0041 (12)	−0.0017 (12)
C10	0.0319 (14)	0.0280 (14)	0.0274 (13)	0.0071 (12)	0.0084 (11)	0.0002 (11)
C11	0.0320 (14)	0.0287 (14)	0.0287 (14)	0.0089 (12)	0.0105 (11)	0.0026 (11)
C12	0.0443 (17)	0.0357 (16)	0.0342 (15)	0.0159 (13)	0.0177 (13)	0.0100 (12)
C13	0.0488 (19)	0.0447 (19)	0.0476 (18)	0.0138 (15)	0.0260 (15)	0.0163 (15)
C14	0.0453 (18)	0.0354 (17)	0.070 (2)	0.0027 (14)	0.0307 (17)	0.0137 (16)
C15	0.0370 (16)	0.0318 (16)	0.0503 (18)	0.0004 (13)	0.0131 (14)	−0.0021 (14)
C16	0.0475 (18)	0.0480 (19)	0.0289 (15)	0.0103 (15)	0.0046 (13)	−0.0058 (13)
C17	0.058 (2)	0.055 (2)	0.0246 (15)	0.0181 (17)	0.0136 (14)	0.0054 (14)

Geometric parameters (Å, º) top

Cu1—O3	1.947 (2)	C4—C3ⁱ	1.520 (4)
Cu1—O1	1.9545 (19)	C4—H4A	0.9700
Cu1—N1	2.014 (2)	C4—H4B	0.9700
Cu1—N2	2.022 (2)	C6—C7	1.387 (4)
Cu1—O5	2.385 (2)	C6—H6	0.9300
N1—C6	1.329 (3)	C7—C8	1.362 (4)
N1—C10	1.360 (3)	C7—H7	0.9300
N2—C15	1.320 (4)	C8—C9	1.404 (4)
N2—C11	1.362 (3)	C8—H8	0.9300
O1—C1	1.266 (3)	C9—C10	1.401 (4)
O2—C1	1.243 (3)	C9—C16	1.440 (4)
O3—C5	1.267 (3)	C10—C11	1.429 (4)
O4—C5	1.225 (4)	C11—C12	1.402 (4)
O5—H51	0.8897	C12—C13	1.403 (4)
O5—H52	0.8804	C12—C17	1.435 (4)
C1—C2	1.511 (4)	C13—C14	1.359 (4)
C2—C3	1.531 (4)	C13—H13	0.9300
C2—H2A	0.9700	C14—C15	1.401 (4)
C2—H2B	0.9700	C14—H14	0.9300
C3—C4ⁱ	1.520 (4)	C15—H15	0.9300
C3—H3A	0.9700	C16—C17	1.340 (5)
C3—H3B	0.9700	C16—H16	0.9300
C4—C5	1.518 (4)	C17—H17	0.9300

O3—Cu1—O1	91.32 (9)	H4A—C4—H4B	108.2
O3—Cu1—N1	91.85 (9)	O4—C5—O3	125.6 (3)
O1—Cu1—N1	165.65 (9)	O4—C5—C4	119.0 (3)
O3—Cu1—N2	173.39 (9)	O3—C5—C4	115.3 (3)
O1—Cu1—N2	94.62 (9)	N1—C6—C7	122.6 (3)
N1—Cu1—N2	81.69 (9)	N1—C6—H6	118.7
O3—Cu1—O5	99.10 (8)	C7—C6—H6	118.7
O1—Cu1—O5	95.20 (7)	C8—C7—C6	120.0 (3)
N1—Cu1—O5	98.12 (8)	C8—C7—H7	120.0
N2—Cu1—O5	83.28 (8)	C6—C7—H7	120.0
C6—N1—C10	117.9 (2)	C7—C8—C9	119.4 (3)
C6—N1—Cu1	129.16 (18)	C7—C8—H8	120.3
C10—N1—Cu1	112.87 (17)	C9—C8—H8	120.3
C15—N2—C11	117.8 (2)	C10—C9—C8	117.3 (3)
C15—N2—Cu1	129.3 (2)	C10—C9—C16	117.9 (3)
C11—N2—Cu1	112.56 (17)	C8—C9—C16	124.8 (3)
C1—O1—Cu1	108.23 (17)	N1—C10—C9	122.8 (2)
C5—O3—Cu1	125.2 (2)	N1—C10—C11	116.4 (2)
Cu1—O5—H51	91.5	C9—C10—C11	120.7 (2)
Cu1—O5—H52	113.4	N2—C11—C12	123.6 (3)
H51—O5—H52	112.2	N2—C11—C10	116.3 (2)
O2—C1—O1	123.0 (2)	C12—C11—C10	120.0 (2)
O2—C1—C2	120.8 (3)	C11—C12—C13	116.9 (3)
O1—C1—C2	116.1 (3)	C11—C12—C17	118.2 (3)
C1—C2—C3	110.1 (2)	C13—C12—C17	124.9 (3)
C1—C2—H2A	109.6	C14—C13—C12	119.0 (3)
C3—C2—H2A	109.6	C14—C13—H13	120.5
C1—C2—H2B	109.6	C12—C13—H13	120.5
C3—C2—H2B	109.6	C13—C14—C15	120.7 (3)
H2A—C2—H2B	108.1	C13—C14—H14	119.6
C4ⁱ—C3—C2	113.5 (2)	C15—C14—H14	119.6
C4ⁱ—C3—H3A	108.9	N2—C15—C14	121.9 (3)
C2—C3—H3A	108.9	N2—C15—H15	119.1
C4ⁱ—C3—H3B	108.9	C14—C15—H15	119.1
C2—C3—H3B	108.9	C17—C16—C9	121.4 (3)
H3A—C3—H3B	107.7	C17—C16—H16	119.3
C5—C4—C3ⁱ	109.7 (2)	C9—C16—H16	119.3
C5—C4—H4A	109.7	C16—C17—C12	121.8 (3)
C3ⁱ—C4—H4A	109.7	C16—C17—H17	119.1
C5—C4—H4B	109.7	C12—C17—H17	119.1
C3ⁱ—C4—H4B	109.7

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C6–C10 ring

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4	0.89	1.81	2.659 (3)	158
O5—H52···O2ⁱⁱ	0.88	1.89	2.762 (3)	169
C2—H2A···Cg1ⁱⁱ	0.97	2.88	3.754 (3)	151

Symmetry code: (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₅H₆O₄)₂(C₁₂H₁₈N₂)₂(H₂O)₂]
M_r	783.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.2767 (11), 10.5935 (14), 15.5998 (16)
β (°)	107.114 (1)
V (Å³)	1623.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.38
Crystal size (mm)	0.26 × 0.25 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.716, 0.742
No. of measured, independent and observed [I > 2σ(I)] reflections	7937, 2867, 2275
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.083, 1.07
No. of reflections	2867
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C6–C10 ring

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4	0.89	1.81	2.659 (3)	157.9
O5—H52···O2ⁱ	0.88	1.89	2.762 (3)	169.1
C2—H2A···Cg1ⁱ	0.97	2.88	3.754 (3)	151

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Table 2 π-π stacking interactions (Å) top

Cg1 is the centroid of the N1,C6–C10 ring. Cg2 is the centroid of the N2,C11–C15 ring

CgI	CgJ	centroid-to-centroid	interplanar vector	Slippage
Cg1	Cg1ⁱⁱ	3.5599 (17)	3.342	1.226
Cg2	Cg2ⁱⁱⁱ	3.5617 (18)	3.374	1.142

Symmetry codes: (ii)-x,1-y,1-z; (iii) 1-x, 1-y, -z

Slippage = vertical displacement between ring centroids.

Acknowledgements

The project was supported by the Natural Science Foundation of Anhui Provincial Education Commission (No. KJw2008B65ZC) and the Open Foundation of Anhui Key Laboratory of Energetic Materials (No. KLEM2009004).

References

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Volume 67| Part 4| April 2011| Page m411

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