Tetra­ethyl­ammonium 4-hy­droxy­benzoate monohydrate

Li, H.; Liu, P.; Yang, Y.

doi:10.1107/S1600536811024044

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1788

doi:10.1107/S1600536811024044

Open

access

Tetraethylammonium 4-hydroxybenzoate monohydrate

Heping Li,^a Pei Liu ^a and Yunxia Yang ^b ^*

^aHenan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bKey Laboratory of Polymer Materials of Gansu Province, Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, Gansu, People's Republic of China
^*Correspondence e-mail: yangyx80@nwnu.edu.cn

(Received 13 June 2011; accepted 20 June 2011; online 25 June 2011)

In the title compound, C₈H₂₀N⁺·C₇H₅O₃⁻·H₂O, the carboxylate group is slightly out of the plane of the parent benzene ring, the C—C—C—O torsion angles being 2.3 (2) and 2.0 (2)°. The carboxylate group and the hydroxy group form O—H⋯O hydrogen bonds, generating a head-to-tail chain along the b axis. Neighbouring hydrogen-bonded chains are linked by the water molecule, generating two independent O—H⋯O donor hydrogen bonds. The carboxylate group thus constructs a hydrogen-bonded host layer parallel to (10 $[\overline{1}]$ ). The tetraethylammonium cation is contained between these layers, forming a sandwich-like structure with an approximate interlayer distance of 10.03 Å.

Related literature

p-Hydroxybenzoic acid has been found to interact with varied cations, such as decyl(trimethyl)ammonium and hexamethonium, to form different crystal structures, see: Marsh & Spek (2001 ); Yang et al. (2010 ).

Experimental

Crystal data

C₈H₂₀N⁺·C₇H₅O₃⁻·H₂O
M_r = 285.38
Monoclinic, P 2₁ /n
a = 9.6082 (10) Å
b = 16.2610 (16) Å
c = 10.4478 (10) Å
β = 96.378 (1)°
V = 1622.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.66 × 0.37 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.947, T_max = 0.984
7411 measured reflections
3774 independent reflections
2730 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.181
S = 1.06
3774 reflections
182 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3ⁱ	0.86	1.74	2.5984 (16)	175
O1W—H1WA⋯O3ⁱⁱ	0.85	2.04	2.850 (2)	161
O1W—H1WB⋯O2ⁱⁱⁱ	0.85	1.94	2.781 (2)	169
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024044/fj2433sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024044/fj2433Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024044/fj2433Isup3.cml

checkCIF report

Comment top

p-Hydroxybenzoic acid has been found to interact with varied cations, such as decyl(trimethyl)ammonium and hexamethonium, to form different crystal structures (Marsh et al., 2001; Yang et al., 2010). In the asymmetric unit of the title compound, (C₂H₅)₄N⁺.C₇H₅O₃^-.H₂O, there exist one p-hydroxybenzoate anion, in which the carboxyl group distorts a small angle with respect to the phenyl ring which has a mean deviation from plane of 0.0041 Å (the related torsion angles are 2.3 (2)° and 2.0 (2)° respectively), one water molecule and one tetraethylammonium cation (Fig. 1). With the help of the water molecule, the hydrogen-bonded chains of p-hydroxybenzoate anions extending along the [010] direction are connected with various O—H···O interactions to generate the hydrogen-bonded host layers (Fig. 2), which are parallel to the (101) plane and can accommodate the guest species of tetraethylammonium cations to form the final packing structure (Fig. 3). Obviously, water molecule, as a compensate host molecule, plays an important role in generating the hydrogen-bonded layer structure.

For the related crystal structures of p-hydroxybenzoic acid and different cations, see: Marsh et al., (2001), Yang et al., (2010).

Related literature top

Experimental top

p-Hydroxybenzoic acid (0.25 mmol, 0.035 g) was dissolved in small amount of water-ethanol (50:100 v/v) mixture and a 25% aqueous solution of tetraethylammonium hydroxide was added to neutralize the acid. Colorless block crystals separated after several weeks.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot of the title compound at the 30% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded linking pattern of the host layer in the crystal structure of the title compound.
	Fig. 3. Packing diagram of the title compound; all hydrogen atoms bonded to carbon are omitted for clarity and the cations are represented with the open bonds.

Tetraethylammonium 4-hydroxybenzoate monohydrate top

Crystal data top

C₈H₂₀N⁺·C₇H₅O₃⁻·H₂O	F(000) = 624
M_r = 285.38	D_x = 1.168 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2665 reflections
a = 9.6082 (10) Å	θ = 3.1–27.5°
b = 16.2610 (16) Å	µ = 0.08 mm⁻¹
c = 10.4478 (10) Å	T = 296 K
β = 96.378 (1)°	Block, colorless
V = 1622.2 (3) Å³	0.66 × 0.37 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3774 independent reflections
Radiation source: fine-focus sealed tube	2730 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 27.7°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→12
T_min = 0.947, T_max = 0.984	k = −21→16
7411 measured reflections	l = −12→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.181	w = 1/[σ²(F_o²) + (0.0974P)² + 0.3052P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3774 reflections	Δρ_max = 0.35 e Å⁻³
182 parameters	Δρ_min = −0.19 e Å⁻³
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (3)

Crystal data top

C₈H₂₀N⁺·C₇H₅O₃⁻·H₂O	V = 1622.2 (3) Å³
M_r = 285.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6082 (10) Å	µ = 0.08 mm⁻¹
b = 16.2610 (16) Å	T = 296 K
c = 10.4478 (10) Å	0.66 × 0.37 × 0.20 mm
β = 96.378 (1)°

Data collection top

Bruker SMART APEX diffractometer	3774 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2730 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.984	R_int = 0.015
7411 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	4 restraints
wR(F²) = 0.181	H-atom parameters constrained
S = 1.06	Δρ_max = 0.35 e Å⁻³
3774 reflections	Δρ_min = −0.19 e Å⁻³
182 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	0.18857 (16)	0.99878 (8)	0.16322 (14)	0.0403 (3)
C2	0.14101 (18)	0.92648 (9)	0.10187 (15)	0.0455 (4)
H2A	0.0914	0.9286	0.0203	0.055*
C3	0.16740 (16)	0.85171 (9)	0.16210 (15)	0.0418 (4)
H3A	0.1363	0.8037	0.1197	0.050*
C4	0.23956 (15)	0.84650 (9)	0.28496 (14)	0.0378 (3)
C5	0.28608 (17)	0.91927 (9)	0.34473 (14)	0.0425 (4)
H5A	0.3344	0.9173	0.4269	0.051*
C6	0.26236 (17)	0.99454 (9)	0.28514 (15)	0.0432 (4)
H6A	0.2958	1.0424	0.3266	0.052*
C7	0.26794 (17)	0.76486 (9)	0.35068 (16)	0.0459 (4)
C8	0.3736 (2)	0.18451 (12)	0.6489 (2)	0.0616 (5)
H8A	0.4666	0.1638	0.6772	0.074*
H8B	0.3597	0.1803	0.5558	0.074*
C9	0.3679 (3)	0.27388 (14)	0.6854 (3)	0.0901 (8)
H9A	0.4380	0.3038	0.6459	0.135*
H9B	0.3850	0.2792	0.7773	0.135*
H9C	0.2770	0.2957	0.6562	0.135*
C10	0.2876 (3)	0.13132 (17)	0.8501 (2)	0.0807 (7)
H10A	0.2722	0.1871	0.8782	0.097*
H10B	0.2170	0.0967	0.8824	0.097*
C11	0.4301 (3)	0.1034 (3)	0.9102 (3)	0.1159 (11)
H11A	0.4337	0.1059	1.0023	0.174*
H11B	0.5008	0.1386	0.8820	0.174*
H11C	0.4462	0.0478	0.8844	0.174*
C12	0.1202 (2)	0.15932 (15)	0.6641 (2)	0.0728 (6)
H12A	0.1101	0.2136	0.7003	0.087*
H12B	0.0550	0.1231	0.7008	0.087*
C13	0.0797 (3)	0.1640 (2)	0.5198 (3)	0.1107 (11)
H13A	−0.0148	0.1837	0.5028	0.166*
H13B	0.0863	0.1103	0.4828	0.166*
H13C	0.1418	0.2009	0.4824	0.166*
C14	0.2893 (3)	0.04401 (13)	0.6544 (2)	0.0742 (6)
H14A	0.3847	0.0273	0.6828	0.089*
H14B	0.2791	0.0457	0.5611	0.089*
C15	0.1902 (4)	−0.02043 (18)	0.6972 (4)	0.1230 (13)
H15A	0.2104	−0.0727	0.6607	0.185*
H15B	0.0954	−0.0051	0.6684	0.185*
H15C	0.2019	−0.0243	0.7894	0.185*
O1	0.15893 (14)	1.07037 (7)	0.10032 (11)	0.0582 (4)
H1A	0.2006	1.1118	0.1392	0.087*
O2	0.33056 (16)	0.76395 (8)	0.46118 (13)	0.0680 (4)
O3	0.22788 (15)	0.70078 (7)	0.28835 (14)	0.0638 (4)
N1	0.26670 (15)	0.12929 (9)	0.70443 (14)	0.0503 (4)
O1W	0.5320 (2)	0.14390 (11)	0.3390 (2)	0.0996 (7)
H1WA	0.4672	0.1691	0.2931	0.149*
H1WB	0.5733	0.1776	0.3931	0.149*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0476 (8)	0.0300 (7)	0.0427 (8)	−0.0005 (6)	0.0027 (6)	0.0021 (6)
C2	0.0564 (9)	0.0385 (8)	0.0393 (8)	−0.0032 (7)	−0.0053 (7)	0.0000 (6)
C3	0.0492 (8)	0.0299 (7)	0.0451 (8)	−0.0055 (6)	0.0000 (6)	−0.0037 (6)
C4	0.0400 (7)	0.0301 (7)	0.0430 (8)	−0.0015 (5)	0.0034 (6)	0.0004 (6)
C5	0.0515 (9)	0.0348 (7)	0.0395 (8)	−0.0012 (6)	−0.0033 (6)	−0.0005 (6)
C6	0.0562 (9)	0.0284 (7)	0.0434 (8)	−0.0030 (6)	−0.0008 (7)	−0.0045 (6)
C7	0.0498 (9)	0.0318 (7)	0.0542 (9)	−0.0047 (6)	−0.0030 (7)	0.0046 (6)
C8	0.0608 (11)	0.0550 (10)	0.0710 (12)	−0.0007 (8)	0.0169 (9)	0.0034 (9)
C9	0.107 (2)	0.0529 (13)	0.109 (2)	−0.0090 (12)	0.0082 (15)	−0.0034 (12)
C10	0.0904 (16)	0.0989 (18)	0.0554 (12)	0.0158 (13)	0.0194 (11)	0.0025 (11)
C11	0.107 (2)	0.166 (3)	0.0718 (16)	0.019 (2)	−0.0044 (14)	0.0254 (19)
C12	0.0571 (11)	0.0777 (15)	0.0860 (15)	0.0130 (10)	0.0190 (10)	0.0032 (11)
C13	0.0775 (17)	0.160 (3)	0.0901 (19)	0.0169 (18)	−0.0113 (14)	0.0174 (19)
C14	0.0847 (15)	0.0489 (11)	0.0935 (16)	0.0037 (10)	0.0303 (12)	−0.0080 (10)
C15	0.129 (3)	0.0585 (15)	0.190 (4)	−0.0202 (16)	0.057 (3)	−0.0009 (18)
O1	0.0822 (9)	0.0318 (6)	0.0553 (7)	−0.0057 (5)	−0.0164 (6)	0.0071 (5)
O2	0.0993 (11)	0.0417 (7)	0.0567 (8)	−0.0127 (6)	−0.0194 (7)	0.0118 (6)
O3	0.0779 (9)	0.0287 (6)	0.0770 (9)	−0.0041 (5)	−0.0254 (7)	0.0012 (5)
N1	0.0538 (8)	0.0479 (8)	0.0519 (8)	0.0078 (6)	0.0181 (6)	−0.0004 (6)
O1W	0.0941 (12)	0.0703 (11)	0.1225 (15)	0.0175 (9)	−0.0410 (11)	−0.0246 (10)

Geometric parameters (Å, º) top

C1—O1	1.3515 (17)	C10—H10A	0.9700
C1—C6	1.389 (2)	C10—H10B	0.9700
C1—C2	1.392 (2)	C11—H11A	0.9600
C2—C3	1.379 (2)	C11—H11B	0.9600
C2—H2A	0.9300	C11—H11C	0.9600
C3—C4	1.392 (2)	C12—N1	1.505 (2)
C3—H3A	0.9300	C12—C13	1.516 (4)
C4—C5	1.389 (2)	C12—H12A	0.9700
C4—C7	1.505 (2)	C12—H12B	0.9700
C5—C6	1.381 (2)	C13—H13A	0.9600
C5—H5A	0.9300	C13—H13B	0.9600
C6—H6A	0.9300	C13—H13C	0.9600
C7—O2	1.241 (2)	C14—N1	1.506 (2)
C7—O3	1.2658 (19)	C14—C15	1.516 (4)
C8—C9	1.505 (3)	C14—H14A	0.9700
C8—N1	1.526 (2)	C14—H14B	0.9700
C8—H8A	0.9700	C15—H15A	0.9600
C8—H8B	0.9700	C15—H15B	0.9600
C9—H9A	0.9600	C15—H15C	0.9600
C9—H9B	0.9600	O1—H1A	0.8614
C9—H9C	0.9600	O1W—H1WA	0.8477
C10—C11	1.511 (4)	O1W—H1WB	0.8531
C10—N1	1.513 (3)

O1—C1—C6	123.17 (13)	C10—C11—H11A	109.5
O1—C1—C2	117.58 (13)	C10—C11—H11B	109.5
C6—C1—C2	119.25 (13)	H11A—C11—H11B	109.5
C3—C2—C1	120.01 (13)	C10—C11—H11C	109.5
C3—C2—H2A	120.0	H11A—C11—H11C	109.5
C1—C2—H2A	120.0	H11B—C11—H11C	109.5
C2—C3—C4	121.45 (13)	N1—C12—C13	115.08 (19)
C2—C3—H3A	119.3	N1—C12—H12A	108.5
C4—C3—H3A	119.3	C13—C12—H12A	108.5
C5—C4—C3	117.73 (13)	N1—C12—H12B	108.5
C5—C4—C7	120.89 (13)	C13—C12—H12B	108.5
C3—C4—C7	121.38 (13)	H12A—C12—H12B	107.5
C6—C5—C4	121.60 (13)	C12—C13—H13A	109.5
C6—C5—H5A	119.2	C12—C13—H13B	109.5
C4—C5—H5A	119.2	H13A—C13—H13B	109.5
C5—C6—C1	119.96 (13)	C12—C13—H13C	109.5
C5—C6—H6A	120.0	H13A—C13—H13C	109.5
C1—C6—H6A	120.0	H13B—C13—H13C	109.5
O2—C7—O3	123.84 (14)	N1—C14—C15	114.5 (2)
O2—C7—C4	118.63 (13)	N1—C14—H14A	108.6
O3—C7—C4	117.51 (14)	C15—C14—H14A	108.6
C9—C8—N1	115.27 (19)	N1—C14—H14B	108.6
C9—C8—H8A	108.5	C15—C14—H14B	108.6
N1—C8—H8A	108.5	H14A—C14—H14B	107.6
C9—C8—H8B	108.5	C14—C15—H15A	109.5
N1—C8—H8B	108.5	C14—C15—H15B	109.5
H8A—C8—H8B	107.5	H15A—C15—H15B	109.5
C8—C9—H9A	109.5	C14—C15—H15C	109.5
C8—C9—H9B	109.5	H15A—C15—H15C	109.5
H9A—C9—H9B	109.5	H15B—C15—H15C	109.5
C8—C9—H9C	109.5	C1—O1—H1A	112.5
H9A—C9—H9C	109.5	C12—N1—C14	111.59 (17)
H9B—C9—H9C	109.5	C12—N1—C10	106.87 (15)
C11—C10—N1	115.1 (2)	C14—N1—C10	111.14 (17)
C11—C10—H10A	108.5	C12—N1—C8	110.52 (15)
N1—C10—H10A	108.5	C14—N1—C8	106.31 (14)
C11—C10—H10B	108.5	C10—N1—C8	110.46 (17)
N1—C10—H10B	108.5	H1WA—O1W—H1WB	108.8
H10A—C10—H10B	107.5

O1—C1—C2—C3	−179.51 (15)	C3—C4—C7—O3	2.3 (2)
C6—C1—C2—C3	−0.1 (3)	C13—C12—N1—C14	−59.8 (3)
C1—C2—C3—C4	0.9 (3)	C13—C12—N1—C10	178.5 (2)
C2—C3—C4—C5	−0.8 (2)	C13—C12—N1—C8	58.3 (3)
C2—C3—C4—C7	179.84 (15)	C15—C14—N1—C12	−58.3 (3)
C3—C4—C5—C6	−0.1 (2)	C15—C14—N1—C10	60.9 (3)
C7—C4—C5—C6	179.22 (15)	C15—C14—N1—C8	−178.9 (2)
C4—C5—C6—C1	1.0 (3)	C11—C10—N1—C12	−179.8 (2)
O1—C1—C6—C5	178.56 (15)	C11—C10—N1—C14	58.2 (3)
C2—C1—C6—C5	−0.9 (2)	C11—C10—N1—C8	−59.5 (3)
C5—C4—C7—O2	2.0 (2)	C9—C8—N1—C12	57.8 (2)
C3—C4—C7—O2	−178.72 (16)	C9—C8—N1—C14	179.1 (2)
C5—C4—C7—O3	−176.97 (16)	C9—C8—N1—C10	−60.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱ	0.86	1.74	2.5984 (16)	175
O1W—H1WA···O3ⁱⁱ	0.85	2.04	2.850 (2)	161
O1W—H1WB···O2ⁱⁱⁱ	0.85	1.94	2.781 (2)	169

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

Experimental details

Crystal data
Chemical formula	C₈H₂₀N⁺·C₇H₅O₃⁻·H₂O
M_r	285.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.6082 (10), 16.2610 (16), 10.4478 (10)
β (°)	96.378 (1)
V (Å³)	1622.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.66 × 0.37 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	7411, 3774, 2730
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.181, 1.06
No. of reflections	3774
No. of parameters	182
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.19

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱ	0.86	1.74	2.5984 (16)	175
O1W—H1WA···O3ⁱⁱ	0.85	2.04	2.850 (2)	161
O1W—H1WB···O2ⁱⁱⁱ	0.85	1.94	2.781 (2)	169

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

Acknowledgements

We thank Northwest Normal University for supporting this study.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconson, USA. Google Scholar
Marsh, R. E. & Spek, A. L. (2001). Acta Cryst. B57, 800–805. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, Y. X., Li, K., Wang, Y. J. & Li, Q. (2010). Beijing Shifan Dax. Xue. Zir. Kex. (J. B. Norm. Univ.), 46, 160–165. CAS Google Scholar