(3-Pyrid­yl)methanaminium 4-nitro­phenolate 4-nitro­phenol solvate

Zhang, Y.; Han, M.T.

doi:10.1107/S1600536810021902

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1649

doi:10.1107/S1600536810021902

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(3-Pyridyl)methanaminium 4-nitrophenolate 4-nitrophenol solvate

Yuan Zhang ^a ^* and Meng Ting Han ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical, Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: zhangshelley86@hotmail.com

(Received 23 May 2010; accepted 8 June 2010; online 16 June 2010)

In the crystal structure of the title compound, C₆H₉N₂⁺·C₆H₄NO₃⁻·C₆H₅NO₃, ions and molecules are connected via intermolecular N—H⋯O, N—H⋯N, O—H⋯O and C—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For background to the development of ferroelectric pure organic or inorganic compounds, see: Haertling et al. (1999 ); Homes et al. (2001 ). For our recent reports on the synthesis of a variety of compounds which have potential piezoelectric and ferroelectric properties, see: Fu et al. (2009 ); Hang et al. (2009 ).

Experimental

Crystal data

C₆H₉N₂⁺·C₆H₄NO₃⁻·C₆H₅NO₃
M_r = 386.36
Triclinic, $[P \overline 1]$
a = 6.3666 (13) Å
b = 7.4451 (15) Å
c = 21.262 (4) Å
α = 92.41 (3)°
β = 95.56 (3)°
γ = 113.99 (3)°
V = 912.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.825, T_max = 1.000
9547 measured reflections
4182 independent reflections
2896 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.140
S = 1.05
4182 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.89	2.09	2.952 (2)	162
N1—H1B⋯O3ⁱⁱ	0.89	1.87	2.753 (2)	169
N1—H1C⋯N2ⁱⁱⁱ	0.89	2.16	2.866 (2)	136
O4—H4A⋯O3	0.96	1.58	2.5385 (19)	173
C1—H1D⋯O5^iv	0.93	2.52	3.229 (3)	133
C2—H2A⋯O6^v	0.93	2.58	3.327 (3)	138
C8—H10A⋯O4ⁱⁱⁱ	0.93	2.54	3.462 (3)	169
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y+1, z; (iii) x-1, y, z; (iv) -x+2, -y+1, -z+1; (v) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: 10.1107/S1600536810021902/jh2162sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021902/jh2162Isup2.hkl

checkCIF report

Comment top

At present, much attention in ferroelectric material field is focused on developing ferroelectric pure organic or inorganic compounds (Haertling et al. 1999; Homes et al. 2001). Recently we have reported the synthesis of a variety of compounds (Fu et al., 2009; Hang et al., 2009), which have potential piezoelectric and ferroelectric properties. In order to find more dielectric ferroelectric materials, we investigate the physical properties of the title compound(Fig. 1). The dielectric constant of the title compound as a function of temperature indicates that the permittivity is basically temperature-independent (dielectric constant equaling to 2.8 to 4.6), suggesting that this compound should be not a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Similarly, below the melting point (399 K) of the compound, the dielectric constant as a function of temperature also goes smoothly, and there is no dielectric anomaly observed (dielectric constant equaling to 2.8 to 4.6).Herein, we report the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. There are one 4-nitrophenolate anion, an substituted ammonium cation and a neutral 4-nitrophenol molecule in the asymmetric unit. Molecules of the title compound have normal geometric parameters. The bond lengths and angles are within their normal ranges. All pyridine rings are, of course, planar. As can be seen from the packing diagram (Fig. 2), molecules are connected via intermolecular C—H···O and O—H···N hydrogen bonds to form a three dimensional network. Dipole–dipole and van der Waals interactions are effective in the molecular packing.

Related literature top

For background to the development of ferroelectric pure organic or inorganic compounds, see: Haertling et al. (1999); Homes et al. (2001). For our recent reports on the synthesis of a variety of compounds which have potential piezoelectric and ferroelectric properties, see: Fu et al. (2009); Hang et al. (2009).

Experimental top

4-nitrophenol (2.085 g, 0.015 mol) was added slowly to a solution of pyridin-3-ylmethanamine (1.62 g, 0.015 mol) in methanol.After several days, the title compound was formed and recrystallized from solution to afford colourless prismatic crystals suitable for X-ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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. Perspective structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis showing the hydrogen bondings network. Some of the H atoms have been ommitted for clarity.

(3-Pyridyl)methanaminium 4-nitrophenolate 4-nitrophenol solvate top

Crystal data top

C₆H₉N₂⁺·C₆H₄NO₃⁻·C₆H₅nO₃	Z = 2
M_r = 386.36	F(000) = 404
Triclinic, P1	D_x = 1.406 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3666 (13) Å	Cell parameters from 4182 reflections
b = 7.4451 (15) Å	θ = 2.6–27.5°
c = 21.262 (4) Å	µ = 0.11 mm⁻¹
α = 92.41 (3)°	T = 293 K
β = 95.56 (3)°	Prism, colorless
γ = 113.99 (3)°	0.20 × 0.20 × 0.20 mm
V = 912.8 (3) Å³

Data collection top

Rigaku Mercury2 diffractometer	4182 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD_Profile_fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
T_min = 0.825, T_max = 1.000	l = −27→27
9547 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0576P)² + 0.2125P] where P = (F_o² + 2F_c²)/3
4182 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₆H₉N₂⁺·C₆H₄NO₃⁻·C₆H₅nO₃	γ = 113.99 (3)°
M_r = 386.36	V = 912.8 (3) Å³
Triclinic, P1	Z = 2
a = 6.3666 (13) Å	Mo Kα radiation
b = 7.4451 (15) Å	µ = 0.11 mm⁻¹
c = 21.262 (4) Å	T = 293 K
α = 92.41 (3)°	0.20 × 0.20 × 0.20 mm
β = 95.56 (3)°

Data collection top

Rigaku Mercury2 diffractometer	4182 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2896 reflections with I > 2σ(I)
T_min = 0.825, T_max = 1.000	R_int = 0.034
9547 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
4182 reflections	Δρ_min = −0.25 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
O3	0.3538 (2)	0.0490 (2)	0.19323 (6)	0.0471 (3)
O4	0.7520 (2)	0.0641 (2)	0.23068 (6)	0.0490 (4)
H4A	0.6012	0.0634	0.2194	0.074*
C10	0.2665 (3)	0.2431 (3)	0.01944 (8)	0.0389 (4)
N3	0.2243 (3)	0.2980 (2)	−0.04283 (8)	0.0481 (4)
C7	0.3307 (3)	0.1152 (3)	0.13814 (8)	0.0369 (4)
O2	0.3528 (3)	0.2970 (2)	−0.08282 (7)	0.0609 (4)
O1	0.0584 (3)	0.3409 (3)	−0.05577 (7)	0.0687 (5)
C9	0.1125 (3)	0.2297 (3)	0.06264 (9)	0.0442 (5)
H9A	−0.0114	0.2633	0.0522	0.053*
C8	0.1442 (3)	0.1664 (3)	0.12100 (9)	0.0438 (4)
H10A	0.0403	0.1572	0.1499	0.053*
C13	0.8177 (3)	0.1128 (3)	0.29326 (8)	0.0388 (4)
C12	0.4868 (3)	0.1361 (3)	0.09345 (9)	0.0445 (5)
H12A	0.6144	0.1074	0.1040	0.053*
C11	0.4552 (3)	0.1978 (3)	0.03479 (9)	0.0445 (5)
H11A	0.5589	0.2091	0.0057	0.053*
C18	0.6884 (3)	0.1667 (3)	0.33310 (9)	0.0488 (5)
H18A	0.5513	0.1731	0.3165	0.059*
C16	0.9669 (4)	0.2016 (3)	0.42097 (9)	0.0523 (5)
C14	1.0262 (3)	0.1105 (3)	0.31834 (9)	0.0476 (5)
H14A	1.1167	0.0798	0.2917	0.057*
C15	1.0994 (4)	0.1534 (3)	0.38222 (10)	0.0530 (5)
H15A	1.2379	0.1497	0.3991	0.064*
C17	0.7627 (4)	0.2106 (3)	0.39719 (10)	0.0570 (6)
H17A	0.6761	0.2459	0.4240	0.068*
O5	1.2363 (4)	0.2523 (5)	0.50752 (9)	0.1289 (10)
O6	0.9263 (4)	0.2807 (4)	0.52407 (9)	0.1112 (8)
N4	1.0492 (5)	0.2488 (4)	0.48875 (10)	0.0792 (7)
N1	−0.0537 (3)	0.7260 (2)	0.20070 (7)	0.0414 (4)
H1A	−0.1686	0.7006	0.1696	0.062*
H1B	0.0690	0.8325	0.1935	0.062*
H1C	−0.0989	0.7476	0.2375	0.062*
N2	0.5902 (3)	0.6209 (3)	0.28249 (8)	0.0502 (4)
C1	0.5678 (4)	0.6498 (3)	0.34345 (9)	0.0485 (5)
H1D	0.6919	0.6693	0.3739	0.058*
C4	0.2013 (3)	0.5896 (3)	0.25514 (9)	0.0398 (4)
C5	0.4074 (3)	0.5913 (3)	0.24015 (9)	0.0466 (5)
H5A	0.4205	0.5703	0.1975	0.056*
C3	0.1849 (3)	0.6229 (3)	0.31859 (9)	0.0469 (5)
H3A	0.0499	0.6254	0.3309	0.056*
C6	0.0087 (4)	0.5549 (3)	0.20322 (10)	0.0491 (5)
H6A	0.0559	0.5305	0.1628	0.059*
H6C	−0.1262	0.4384	0.2101	0.059*
C2	0.3695 (3)	0.6522 (3)	0.36331 (9)	0.0490 (5)
H2A	0.3605	0.6733	0.4062	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0441 (8)	0.0624 (9)	0.0358 (7)	0.0228 (7)	0.0022 (6)	0.0128 (6)
O4	0.0430 (8)	0.0695 (9)	0.0332 (7)	0.0231 (7)	−0.0002 (6)	0.0017 (6)
C10	0.0433 (10)	0.0396 (10)	0.0295 (9)	0.0146 (8)	−0.0031 (7)	0.0008 (7)
N3	0.0561 (11)	0.0485 (10)	0.0345 (9)	0.0185 (8)	−0.0034 (8)	0.0026 (7)
C7	0.0358 (9)	0.0402 (10)	0.0305 (9)	0.0128 (8)	−0.0018 (7)	0.0015 (7)
O2	0.0672 (10)	0.0792 (11)	0.0352 (8)	0.0280 (8)	0.0083 (7)	0.0124 (7)
O1	0.0807 (12)	0.0936 (12)	0.0480 (9)	0.0546 (10)	−0.0054 (8)	0.0147 (8)
C9	0.0437 (11)	0.0536 (11)	0.0404 (10)	0.0265 (9)	−0.0004 (8)	0.0038 (9)
C8	0.0433 (11)	0.0561 (12)	0.0370 (10)	0.0249 (9)	0.0074 (8)	0.0044 (9)
C13	0.0389 (10)	0.0422 (10)	0.0324 (9)	0.0143 (8)	0.0020 (7)	0.0050 (8)
C12	0.0398 (10)	0.0605 (12)	0.0386 (10)	0.0267 (9)	0.0014 (8)	0.0068 (9)
C11	0.0412 (10)	0.0563 (12)	0.0360 (10)	0.0198 (9)	0.0059 (8)	0.0037 (8)
C18	0.0410 (11)	0.0651 (13)	0.0432 (11)	0.0253 (10)	0.0035 (8)	0.0031 (9)
C16	0.0573 (13)	0.0654 (13)	0.0322 (10)	0.0250 (11)	−0.0012 (9)	0.0009 (9)
C14	0.0441 (11)	0.0602 (12)	0.0420 (11)	0.0264 (10)	0.0024 (8)	−0.0029 (9)
C15	0.0458 (12)	0.0689 (14)	0.0451 (12)	0.0283 (11)	−0.0090 (9)	−0.0022 (10)
C17	0.0527 (13)	0.0778 (15)	0.0436 (12)	0.0291 (12)	0.0128 (9)	−0.0005 (11)
O5	0.1125 (19)	0.228 (3)	0.0508 (12)	0.088 (2)	−0.0332 (12)	−0.0189 (14)
O6	0.1272 (19)	0.172 (2)	0.0420 (10)	0.0706 (18)	0.0152 (11)	−0.0083 (12)
N4	0.0898 (17)	0.1082 (18)	0.0373 (11)	0.0416 (14)	−0.0021 (11)	−0.0018 (11)
N1	0.0396 (9)	0.0564 (10)	0.0309 (8)	0.0226 (8)	0.0024 (6)	0.0071 (7)
N2	0.0444 (10)	0.0676 (11)	0.0412 (9)	0.0260 (9)	0.0038 (7)	0.0050 (8)
C1	0.0471 (11)	0.0589 (12)	0.0383 (11)	0.0217 (10)	−0.0015 (8)	0.0085 (9)
C4	0.0421 (10)	0.0377 (10)	0.0379 (10)	0.0159 (8)	−0.0004 (8)	0.0047 (8)
C5	0.0499 (12)	0.0566 (12)	0.0343 (10)	0.0232 (10)	0.0043 (8)	0.0016 (9)
C3	0.0431 (11)	0.0576 (12)	0.0430 (11)	0.0232 (10)	0.0075 (8)	0.0076 (9)
C6	0.0529 (12)	0.0454 (11)	0.0462 (12)	0.0212 (10)	−0.0091 (9)	−0.0012 (9)
C2	0.0507 (12)	0.0643 (13)	0.0329 (10)	0.0235 (10)	0.0088 (8)	0.0081 (9)

Geometric parameters (Å, º) top

O3—C7	1.308 (2)	C14—C15	1.373 (3)
O4—C13	1.344 (2)	C14—H14A	0.9300
O4—H4A	0.9646	C15—H15A	0.9300
C10—C9	1.385 (3)	C17—H17A	0.9300
C10—C11	1.387 (3)	O5—N4	1.209 (3)
C10—N3	1.435 (2)	O6—N4	1.218 (3)
N3—O1	1.232 (2)	N1—C6	1.482 (2)
N3—O2	1.238 (2)	N1—H1A	0.8900
C7—C8	1.409 (3)	N1—H1B	0.8900
C7—C12	1.409 (3)	N1—H1C	0.8900
C9—C8	1.371 (3)	N2—C1	1.336 (3)
C9—H9A	0.9300	N2—C5	1.336 (3)
C8—H10A	0.9300	C1—C2	1.376 (3)
C13—C14	1.389 (3)	C1—H1D	0.9300
C13—C18	1.389 (3)	C4—C5	1.375 (3)
C12—C11	1.372 (3)	C4—C3	1.383 (3)
C12—H12A	0.9300	C4—C6	1.498 (3)
C11—H11A	0.9300	C5—H5A	0.9300
C18—C17	1.378 (3)	C3—C2	1.375 (3)
C18—H18A	0.9300	C3—H3A	0.9300
C16—C15	1.370 (3)	C6—H6A	0.9700
C16—C17	1.377 (3)	C6—H6C	0.9700
C16—N4	1.462 (3)	C2—H2A	0.9300

C13—O4—H4A	110.0	C14—C15—H15A	120.3
C9—C10—C11	121.06 (17)	C16—C17—C18	119.14 (19)
C9—C10—N3	119.04 (17)	C16—C17—H17A	120.4
C11—C10—N3	119.86 (18)	C18—C17—H17A	120.4
O1—N3—O2	121.47 (17)	O5—N4—O6	122.7 (2)
O1—N3—C10	119.44 (17)	O5—N4—C16	118.4 (2)
O2—N3—C10	119.07 (17)	O6—N4—C16	119.0 (2)
O3—C7—C8	120.54 (17)	C6—N1—H1A	109.5
O3—C7—C12	122.14 (16)	C6—N1—H1B	109.5
C8—C7—C12	117.31 (16)	H1A—N1—H1B	109.5
C8—C9—C10	119.43 (17)	C6—N1—H1C	109.5
C8—C9—H9A	120.3	H1A—N1—H1C	109.5
C10—C9—H9A	120.3	H1B—N1—H1C	109.5
C9—C8—C7	121.42 (18)	C1—N2—C5	116.81 (18)
C9—C8—H10A	119.3	N2—C1—C2	123.07 (19)
C7—C8—H10A	119.3	N2—C1—H1D	118.5
O4—C13—C14	117.63 (17)	C2—C1—H1D	118.5
O4—C13—C18	123.06 (17)	C5—C4—C3	117.13 (18)
C14—C13—C18	119.31 (17)	C5—C4—C6	119.56 (18)
C11—C12—C7	121.54 (17)	C3—C4—C6	123.31 (18)
C11—C12—H12A	119.2	N2—C5—C4	124.60 (18)
C7—C12—H12A	119.2	N2—C5—H5A	117.7
C12—C11—C10	119.20 (18)	C4—C5—H5A	117.7
C12—C11—H11A	120.4	C2—C3—C4	119.60 (19)
C10—C11—H11A	120.4	C2—C3—H3A	120.2
C17—C18—C13	120.22 (19)	C4—C3—H3A	120.2
C17—C18—H18A	119.9	N1—C6—C4	111.67 (16)
C13—C18—H18A	119.9	N1—C6—H6A	109.3
C15—C16—C17	121.48 (19)	C4—C6—H6A	109.3
C15—C16—N4	118.6 (2)	N1—C6—H6C	109.3
C17—C16—N4	119.9 (2)	C4—C6—H6C	109.3
C15—C14—C13	120.36 (19)	H6A—C6—H6C	107.9
C15—C14—H14A	119.8	C3—C2—C1	118.79 (19)
C13—C14—H14A	119.8	C3—C2—H2A	120.6
C16—C15—C14	119.43 (19)	C1—C2—H2A	120.6
C16—C15—H15A	120.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.89	2.09	2.952 (2)	162
N1—H1B···O3ⁱⁱ	0.89	1.87	2.753 (2)	169
N1—H1C···N2ⁱⁱⁱ	0.89	2.16	2.866 (2)	136
O4—H4A···O3	0.96	1.58	2.5385 (19)	173
C1—H1D···O5^iv	0.93	2.52	3.229 (3)	133
C2—H2A···O6^v	0.93	2.58	3.327 (3)	138
C8—H10A···O4ⁱⁱⁱ	0.93	2.54	3.462 (3)	169

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

Experimental details

Crystal data
Chemical formula	C₆H₉N₂⁺·C₆H₄NO₃⁻·C₆H₅nO₃
M_r	386.36
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.3666 (13), 7.4451 (15), 21.262 (4)
α, β, γ (°)	92.41 (3), 95.56 (3), 113.99 (3)
V (Å³)	912.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.825, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9547, 4182, 2896
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.140, 1.05
No. of reflections	4182
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25

Computer programs: CrystalClear (Rigaku, 2005), 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
N1—H1A···O2ⁱ	0.89	2.09	2.952 (2)	161.9
N1—H1B···O3ⁱⁱ	0.89	1.87	2.753 (2)	168.9
N1—H1C···N2ⁱⁱⁱ	0.89	2.16	2.866 (2)	136.3
O4—H4A···O3	0.96	1.58	2.5385 (19)	173.3
C1—H1D···O5^iv	0.93	2.52	3.229 (3)	133.4
C2—H2A···O6^v	0.93	2.58	3.327 (3)	138.0
C8—H10A···O4ⁱⁱⁱ	0.93	2.54	3.462 (3)	168.8

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

Acknowledgements

The authors are grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

Fu, D. W., Ge, J. Z., Dai, J., Ye, H. Y. & Qu, Z. R. (2009). Inorg. Chem. Commun. 12, 994–997. Web of Science CSD CrossRef CAS Google Scholar
Haertling, G. H. (1999). J. Am. Ceram. Soc. 82, 797–810. CrossRef CAS Google Scholar
Hang, T., Fu, D. W., Ye, Q. & Xiong, R. G. (2009). Cryst. Growth Des. 5, 2026–2029. Web of Science CSD CrossRef Google Scholar
Homes, C. C., Vogt, T., Shapiro, S. M., Wakimoto, S. & Ramirez, A. P. (2001). Science, 293, 673–676. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar