4-[(2′-Cyano­biphenyl-4-yl)meth­yl]morpholin-4-ium perchlorate

Ou-Yang, H.-Y.

doi:10.1107/S1600536812012792

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1236

doi:10.1107/S1600536812012792

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4-[(2′-Cyanobiphenyl-4-yl)methyl]morpholin-4-ium perchlorate

Hua-Yong Ou-Yang ^a ^*

^aDepartment of Chemical Engineering, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
^*Correspondence e-mail: ouyanghuay@126.com

(Received 16 March 2012; accepted 23 March 2012; online 31 March 2012)

In the title salt, C₁₈H₁₉N₂O⁺·ClO₄⁻, the morpholinium ring adopts a chair conformation, while the two benzene rings make a dihedral angle of 62.65 (17)°. Intermolecular N—H⋯N hydrogen bonds and weak C—H⋯O interactions occur in the crystal structure.

Related literature

The title complound was investigated as part of a search for dielectric ferroelectric materials. For background to ferroelectric materials, see: Haertling (1999 ); Homes et al. (2001 ).

Experimental

Crystal data

C₁₈H₁₉N₂O⁺·ClO₄⁻
M_r = 378.80
Monoclinic, C 2/c
a = 22.997 (5) Å
b = 10.679 (2) Å
c = 14.899 (3) Å
β = 92.96 (3)°
V = 3654.2 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
18531 measured reflections
4191 independent reflections
2478 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.202
S = 1.04
4191 reflections
235 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.82	2.12	2.921 (4)	166
C2—H2B⋯O4ⁱⁱ	0.97	2.57	3.255 (5)	128
C5—H5B⋯O4ⁱⁱⁱ	0.97	2.59	3.515 (6)	161
C5—H5C⋯O4^iv	0.97	2.57	3.474 (7)	154
Symmetry codes: (i) $[x, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812012792/xu5487sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012792/xu5487Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012792/xu5487Isup3.cml

checkCIF report

Comment top

At present, much attention in ferroelectric material field is focused on developing ferroelectric pure organic or inorganic compounds (Haertling, 1999; Homes et al., 2001). In order to find more dielectric ferroelectric materials, we investigate the physical properties of the title compound. Here we report the synthesis and crystal structure of the title compound, 4-((2'-cyanobiphenyl-4-yl)methyl)morpholin-4-ium perchlorate (Fig. 1).

The bond distances and bond angles in the title compound agree very well with the corresponding distances and angles reported for a closely related compound. In this structure, the intermolecular N–H···N and C–H···O hydrogen bonds link the cations and anions to chains (Table 1). The dihedral angle between the benzene rings in the cation is 62.65 (17).

Related literature top

The title complound was investigated as part of a search for dielectric ferroelectric materials. For background to ferroelectric materials, see: Haertling (1999); Homes et al. (2001).

Experimental top

To a stirred solution of 4'-(morpholinomethyl)biphenyl-2-carbonitrile (5.56 g, 0.02 mol) in 30 mL of methanol, perchloric acid (2.87 g, 0.02 mol) was added at the room temperature. The precipitate was filtered and washed with a small amount of ethanol 95%. Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of a solution of the title compound in water at room temperature.

Structure description top

The title complound was investigated as part of a search for dielectric ferroelectric materials. For background to ferroelectric materials, see: Haertling (1999); Homes et al. (2001).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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.

4-[(2'-Cyanobiphenyl-4-yl)methyl]morpholin-4-ium perchlorate top

Crystal data top

C₁₈H₁₉N₂O⁺·ClO₄⁻	F(000) = 1584
M_r = 378.80	D_x = 1.377 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4191 reflections
a = 22.997 (5) Å	θ = 2.6–27.5°
b = 10.679 (2) Å	µ = 0.24 mm⁻¹
c = 14.899 (3) Å	T = 293 K
β = 92.96 (3)°	Prism, colorless
V = 3654.2 (13) Å³	0.20 × 0.20 × 0.20 mm
Z = 8

Data collection top

Rigaku Mercury2 diffractometer	2478 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.066
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
Detector resolution: 13.6612 pixels mm^-1	h = −29→29
CCD_Profile_fitting scans	k = −13→13
18531 measured reflections	l = −19→19
4191 independent 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0836P)² + 4.9367P] where P = (F_o² + 2F_c²)/3
4191 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.59 e Å⁻³
1 restraint	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₈H₁₉N₂O⁺·ClO₄⁻	V = 3654.2 (13) Å³
M_r = 378.80	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.997 (5) Å	µ = 0.24 mm⁻¹
b = 10.679 (2) Å	T = 293 K
c = 14.899 (3) Å	0.20 × 0.20 × 0.20 mm
β = 92.96 (3)°

Data collection top

Rigaku Mercury2 diffractometer	2478 reflections with I > 2σ(I)
18531 measured reflections	R_int = 0.066
4191 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	1 restraint
wR(F²) = 0.202	H-atom parameters constrained
S = 1.04	Δρ_max = 0.59 e Å⁻³
4191 reflections	Δρ_min = −0.34 e Å⁻³
235 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
Cl1	0.14467 (4)	0.33074 (8)	0.21821 (6)	0.0575 (3)
O2	0.15678 (19)	0.4547 (4)	0.2333 (4)	0.169 (2)
O3	0.08570 (14)	0.3054 (5)	0.2221 (3)	0.1361 (16)
O4	0.1785 (2)	0.2616 (5)	0.2795 (3)	0.165 (2)
O5	0.16055 (18)	0.3058 (5)	0.1321 (3)	0.1407 (16)
N1	0.18775 (11)	0.9619 (2)	0.12783 (16)	0.0469 (6)
H1	0.1571	0.9991	0.1172	0.070*
C11	0.09773 (15)	0.9566 (3)	0.2946 (2)	0.0544 (8)
H11A	0.0957	1.0410	0.2796	0.065*
C9	0.05497 (14)	0.7774 (3)	0.3637 (2)	0.0491 (8)
C12	0.01047 (14)	0.7227 (3)	0.4209 (2)	0.0484 (8)
C18	0.04350 (14)	0.8644 (3)	0.5429 (2)	0.0481 (8)
N2	0.07272 (13)	0.9427 (3)	0.57063 (19)	0.0621 (8)
C6	0.14489 (14)	0.8859 (3)	0.27003 (19)	0.0511 (8)
C17	0.00559 (13)	0.7666 (3)	0.5091 (2)	0.0456 (7)
O1	0.22810 (13)	0.9243 (3)	−0.04846 (17)	0.0813 (9)
C1	0.18162 (17)	0.8401 (3)	0.0800 (2)	0.0637 (10)
H1A	0.1465	0.7981	0.0974	0.076*
H1B	0.2146	0.7870	0.0966	0.076*
C16	−0.03494 (14)	0.7160 (3)	0.5651 (2)	0.0561 (8)
H16A	−0.0378	0.7466	0.6232	0.067*
C10	0.05393 (15)	0.9032 (3)	0.3408 (2)	0.0529 (8)
H10A	0.0229	0.9526	0.3571	0.063*
C7	0.14461 (17)	0.7581 (4)	0.2892 (2)	0.0691 (11)
H7A	0.1749	0.7079	0.2710	0.083*
C4	0.23714 (16)	1.0349 (4)	0.0925 (2)	0.0612 (9)
H4B	0.2737	0.9941	0.1100	0.073*
H4C	0.2378	1.1183	0.1183	0.073*
C8	0.10025 (18)	0.7053 (4)	0.3347 (3)	0.0687 (11)
H8A	0.1007	0.6197	0.3461	0.082*
C13	−0.02633 (18)	0.6260 (4)	0.3924 (3)	0.0658 (10)
H13A	−0.0239	0.5939	0.3347	0.079*
C5	0.19543 (15)	0.9467 (4)	0.2283 (2)	0.0598 (9)
H5B	0.2300	0.8969	0.2421	0.072*
H5C	0.2017	1.0286	0.2553	0.072*
C2	0.17854 (19)	0.8610 (4)	−0.0204 (3)	0.0775 (12)
H2B	0.1753	0.7808	−0.0508	0.093*
H2C	0.1440	0.9095	−0.0373	0.093*
C3	0.23077 (19)	1.0439 (4)	−0.0083 (3)	0.0776 (12)
H3B	0.1956	1.0901	−0.0254	0.093*
H3C	0.2636	1.0897	−0.0302	0.093*
C15	−0.07050 (16)	0.6209 (4)	0.5342 (3)	0.0669 (10)
H15A	−0.0974	0.5861	0.5714	0.080*
C14	−0.06639 (18)	0.5771 (4)	0.4484 (3)	0.0739 (11)
H14A	−0.0910	0.5132	0.4276	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0575 (5)	0.0613 (5)	0.0536 (5)	−0.0065 (4)	0.0016 (4)	0.0024 (4)
O2	0.138 (4)	0.073 (2)	0.288 (6)	0.009 (2)	−0.070 (4)	−0.045 (3)
O3	0.070 (2)	0.234 (5)	0.105 (3)	−0.045 (3)	0.0218 (18)	−0.030 (3)
O4	0.152 (4)	0.166 (4)	0.172 (4)	−0.017 (3)	−0.058 (3)	0.105 (4)
O5	0.131 (3)	0.204 (5)	0.093 (3)	−0.004 (3)	0.050 (2)	−0.013 (3)
N1	0.0430 (14)	0.0590 (16)	0.0390 (13)	0.0028 (12)	0.0041 (11)	0.0011 (12)
C11	0.065 (2)	0.057 (2)	0.0423 (17)	0.0102 (17)	0.0091 (15)	0.0034 (15)
C9	0.0586 (19)	0.0542 (19)	0.0345 (15)	0.0071 (16)	0.0033 (14)	0.0018 (14)
C12	0.0531 (18)	0.0508 (18)	0.0410 (17)	0.0039 (15)	0.0011 (14)	0.0037 (14)
C18	0.0490 (19)	0.058 (2)	0.0377 (16)	0.0062 (16)	0.0078 (14)	0.0009 (15)
N2	0.0631 (19)	0.070 (2)	0.0531 (17)	−0.0088 (16)	0.0029 (14)	−0.0086 (15)
C6	0.0535 (19)	0.070 (2)	0.0296 (15)	0.0066 (16)	0.0025 (13)	0.0023 (15)
C17	0.0445 (16)	0.0491 (18)	0.0435 (17)	0.0022 (14)	0.0039 (13)	0.0038 (14)
O1	0.088 (2)	0.102 (2)	0.0570 (16)	−0.0190 (17)	0.0321 (14)	−0.0119 (15)
C1	0.067 (2)	0.068 (2)	0.057 (2)	−0.0121 (19)	0.0167 (18)	−0.0106 (18)
C16	0.0545 (19)	0.061 (2)	0.054 (2)	0.0009 (17)	0.0109 (16)	0.0085 (17)
C10	0.059 (2)	0.059 (2)	0.0415 (17)	0.0151 (16)	0.0104 (15)	0.0036 (15)
C7	0.071 (2)	0.076 (3)	0.062 (2)	0.031 (2)	0.0225 (19)	0.018 (2)
C4	0.061 (2)	0.065 (2)	0.058 (2)	−0.0091 (18)	0.0111 (17)	−0.0017 (18)
C8	0.087 (3)	0.057 (2)	0.064 (2)	0.021 (2)	0.021 (2)	0.0148 (18)
C13	0.079 (3)	0.066 (2)	0.052 (2)	−0.010 (2)	−0.0044 (19)	−0.0075 (18)
C5	0.054 (2)	0.089 (3)	0.0355 (16)	−0.0001 (18)	−0.0010 (14)	0.0057 (17)
C2	0.082 (3)	0.101 (3)	0.051 (2)	−0.023 (2)	0.019 (2)	−0.020 (2)
C3	0.084 (3)	0.094 (3)	0.056 (2)	−0.013 (2)	0.019 (2)	0.012 (2)
C15	0.058 (2)	0.068 (2)	0.076 (3)	−0.0089 (19)	0.0103 (19)	0.015 (2)
C14	0.073 (3)	0.061 (2)	0.087 (3)	−0.018 (2)	−0.004 (2)	0.001 (2)

Geometric parameters (Å, º) top

Cl1—O2	1.369 (4)	C1—C2	1.511 (5)
Cl1—O5	1.377 (4)	C1—H1A	0.9700
Cl1—O4	1.383 (4)	C1—H1B	0.9700
Cl1—O3	1.387 (3)	C16—C15	1.369 (5)
N1—C1	1.486 (4)	C16—H16A	0.9300
N1—C4	1.495 (4)	C10—H10A	0.9300
N1—C5	1.507 (4)	C7—C8	1.374 (5)
N1—H1	0.8180	C7—H7A	0.9300
C11—C10	1.373 (5)	C4—C3	1.505 (5)
C11—C6	1.385 (4)	C4—H4B	0.9700
C11—H11A	0.9300	C4—H4C	0.9700
C9—C8	1.382 (5)	C8—H8A	0.9300
C9—C10	1.386 (5)	C13—C14	1.378 (5)
C9—C12	1.485 (4)	C13—H13A	0.9300
C12—C13	1.388 (5)	C5—H5B	0.9700
C12—C17	1.404 (4)	C5—H5C	0.9700
C18—N2	1.136 (4)	C2—H2B	0.9700
C18—C17	1.435 (5)	C2—H2C	0.9700
C6—C7	1.395 (5)	C3—H3B	0.9700
C6—C5	1.494 (5)	C3—H3C	0.9700
C17—C16	1.393 (4)	C15—C14	1.369 (5)
O1—C2	1.407 (5)	C15—H15A	0.9300
O1—C3	1.411 (5)	C14—H14A	0.9300

O2—Cl1—O5	106.2 (3)	C9—C10—H10A	119.3
O2—Cl1—O4	107.8 (3)	C8—C7—C6	120.9 (3)
O5—Cl1—O4	110.1 (3)	C8—C7—H7A	119.5
O2—Cl1—O3	111.9 (3)	C6—C7—H7A	119.5
O5—Cl1—O3	107.9 (3)	N1—C4—C3	110.4 (3)
O4—Cl1—O3	112.8 (3)	N1—C4—H4B	109.6
C1—N1—C4	110.0 (3)	C3—C4—H4B	109.6
C1—N1—C5	112.7 (3)	N1—C4—H4C	109.6
C4—N1—C5	110.7 (3)	C3—C4—H4C	109.6
C1—N1—H1	105.8	H4B—C4—H4C	108.1
C4—N1—H1	109.9	C7—C8—C9	121.1 (3)
C5—N1—H1	107.5	C7—C8—H8A	119.5
C10—C11—C6	120.7 (3)	C9—C8—H8A	119.5
C10—C11—H11A	119.6	C14—C13—C12	120.8 (4)
C6—C11—H11A	119.6	C14—C13—H13A	119.6
C8—C9—C10	117.8 (3)	C12—C13—H13A	119.6
C8—C9—C12	120.9 (3)	C6—C5—N1	114.0 (3)
C10—C9—C12	121.3 (3)	C6—C5—H5B	108.8
C13—C12—C17	117.3 (3)	N1—C5—H5B	108.8
C13—C12—C9	122.9 (3)	C6—C5—H5C	108.8
C17—C12—C9	119.8 (3)	N1—C5—H5C	108.8
N2—C18—C17	178.8 (4)	H5B—C5—H5C	107.7
C11—C6—C7	117.8 (3)	O1—C2—C1	111.5 (3)
C11—C6—C5	120.6 (3)	O1—C2—H2B	109.3
C7—C6—C5	121.5 (3)	C1—C2—H2B	109.3
C16—C17—C12	121.3 (3)	O1—C2—H2C	109.3
C16—C17—C18	119.0 (3)	C1—C2—H2C	109.3
C12—C17—C18	119.7 (3)	H2B—C2—H2C	108.0
C2—O1—C3	109.1 (3)	O1—C3—C4	111.4 (3)
N1—C1—C2	110.2 (3)	O1—C3—H3B	109.3
N1—C1—H1A	109.6	C4—C3—H3B	109.3
C2—C1—H1A	109.6	O1—C3—H3C	109.3
N1—C1—H1B	109.6	C4—C3—H3C	109.3
C2—C1—H1B	109.6	H3B—C3—H3C	108.0
H1A—C1—H1B	108.1	C14—C15—C16	120.0 (4)
C15—C16—C17	119.5 (3)	C14—C15—H15A	120.0
C15—C16—H16A	120.3	C16—C15—H15A	120.0
C17—C16—H16A	120.3	C15—C14—C13	121.1 (4)
C11—C10—C9	121.5 (3)	C15—C14—H14A	119.4
C11—C10—H10A	119.3	C13—C14—H14A	119.4

C8—C9—C12—C13	−62.6 (5)	C5—C6—C7—C8	174.2 (3)
C10—C9—C12—C13	120.2 (4)	C1—N1—C4—C3	51.9 (4)
C8—C9—C12—C17	115.6 (4)	C5—N1—C4—C3	177.1 (3)
C10—C9—C12—C17	−61.7 (4)	C6—C7—C8—C9	−0.8 (6)
C10—C11—C6—C7	3.6 (5)	C10—C9—C8—C7	3.8 (6)
C10—C11—C6—C5	−173.6 (3)	C12—C9—C8—C7	−173.6 (3)
C13—C12—C17—C16	−0.6 (5)	C17—C12—C13—C14	0.9 (5)
C9—C12—C17—C16	−178.9 (3)	C9—C12—C13—C14	179.0 (4)
C13—C12—C17—C18	178.5 (3)	C11—C6—C5—N1	−85.9 (4)
C9—C12—C17—C18	0.3 (4)	C7—C6—C5—N1	97.0 (4)
N2—C18—C17—C16	−35 (18)	C1—N1—C5—C6	−62.2 (4)
N2—C18—C17—C12	146 (18)	C4—N1—C5—C6	174.2 (3)
C4—N1—C1—C2	−51.8 (4)	C3—O1—C2—C1	−62.5 (5)
C5—N1—C1—C2	−175.8 (3)	N1—C1—C2—O1	58.0 (5)
C12—C17—C16—C15	0.5 (5)	C2—O1—C3—C4	62.4 (4)
C18—C17—C16—C15	−178.7 (3)	N1—C4—C3—O1	−57.6 (4)
C6—C11—C10—C9	−0.6 (5)	C17—C16—C15—C14	−0.6 (6)
C8—C9—C10—C11	−3.1 (5)	C16—C15—C14—C13	0.8 (6)
C12—C9—C10—C11	174.2 (3)	C12—C13—C14—C15	−1.0 (6)
C11—C6—C7—C8	−2.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.82	2.12	2.921 (4)	166
C2—H2B···O4ⁱⁱ	0.97	2.57	3.255 (5)	128
C5—H5B···O4ⁱⁱⁱ	0.97	2.59	3.515 (6)	161
C5—H5C···O4^iv	0.97	2.57	3.474 (7)	154

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₂O⁺·ClO₄⁻
M_r	378.80
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	22.997 (5), 10.679 (2), 14.899 (3)
β (°)	92.96 (3)
V (Å³)	3654.2 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury2
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18531, 4191, 2478
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.202, 1.04
No. of reflections	4191
No. of parameters	235
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.34

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.82	2.12	2.921 (4)	166.3
C2—H2B···O4ⁱⁱ	0.97	2.57	3.255 (5)	127.5
C5—H5B···O4ⁱⁱⁱ	0.97	2.59	3.515 (6)	160.7
C5—H5C···O4^iv	0.97	2.57	3.474 (7)	154.4

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

References

Haertling, G. H. (1999). J. Am. Ceram. Soc. A82, 797–810. CrossRef Google Scholar
Homes, C. C., Vogt, T., Shapiro, S. M., Wakimoto, S. & Ramirez, A. P. (2001). Science, A293, 673–676. Web of Science CrossRef 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

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1236

doi:10.1107/S1600536812012792

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