Morpholin-4-ium 4-meth­oxy­benzoate 4-meth­oxy­benzoic acid monohydrate

Feng, L.-P.; Zhao, L.

doi:10.1107/S1600536811023361

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1759

doi:10.1107/S1600536811023361

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Morpholin-4-ium 4-methoxybenzoate 4-methoxybenzoic acid monohydrate

Li-Ping Feng ^a and Liang Zhao ^a ^*

^aDepartment of Chemical & Environmental Engineering, Anyang Institute of Technology, Anyang 455000, People's Republic of China
^*Correspondence e-mail: ayitzhao@yahoo.com.cn

(Received 12 June 2011; accepted 15 June 2011; online 22 June 2011)

In the crystal structure of the title compound, C₄H₁₀NO⁺·C₈H₇O₃⁻·C₈H₈O₃·H₂O, cations, anions and neutral molecules are linked by intermolecular N—H⋯O and O—H⋯O hydrogen bonds into chains running parallel to the c axis. The –CO₂ groups make dihedral angles of 4.6 (3) and 5.7 (4)° with the attached ring in the 4-methoxybenzoic acid molecule and the 4-methoxybenzoate anion, respectively.

Related literature

For related studies on co-crystals of amino derivatives, see: Fu et al. (2010 ); Aminabhavi et al. (1986 ).

Experimental

Crystal data

C₄H₁₀NO⁺·C₈H₇O₃⁻·C₈H₈O₃·H₂O
M_r = 409.43
Monoclinic, P 2₁ /c
a = 21.874 (4) Å
b = 11.753 (2) Å
c = 8.3618 (17) Å
β = 100.63 (3)°
V = 2112.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.30 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.910, T_max = 1.000
21489 measured reflections
4842 independent reflections
2453 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.162
S = 1.03
4842 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5ⁱ	0.90	1.75	2.628 (3)	164
N1—H1B⋯O2	0.90	1.96	2.837 (3)	163
O1—H1⋯O1Wⁱ	0.82	1.76	2.579 (2)	173
O1W—H1WA⋯O4	0.82	1.91	2.714 (2)	167
O1W—H1WB⋯O4ⁱⁱ	0.82	1.91	2.712 (3)	164
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811023361/rz2614sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023361/rz2614Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811023361/rz2614Isup3.cml

checkCIF report

Comment top

The amino derivatives have found wide range of applications in material science, such as magnetic, fluorescent and dielectric behaviors, and there has been an increasing interest in the preparation of amino co-crystal compounds (Aminabhavi et al., 1986; Fu, et al. 2010). We report here the crystal structure of the title compound, morpholin-4-ium 4-methoxybenzoate 4-methoxybenzoic acid monohydrate.

The asymmetric unit of the title commpound is composed of one 4-methoxybenzoate anion, one morpholin-4-ium cation, one 4-methoxybenzoic acid molecule and one water molecule (Fig. 1). The morpholine ring is in a chair conformation. All geometric parameters are in the normal ranges. In the crystal structure, the H atoms bound to N and O atoms are involved in intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) linking ions and neutral molecules into one-dimensional chains parallel to the c-axis (Fig. 2).

Related literature top

For related studies on co-crystals of amino derivatives, see: Fu et al. (2010); Aminabhavi et al. (1986).

Experimental top

A mixture of morpholine (0.4 mmol) 4-methoxybenzoic acid (0.8 mmol) was dissolved in distilled water (10 ml). Colourless crystals suitable for X-ray analysis were obtained after 3 days on slow evaporation of the solvent.

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. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound showing a one-dimensional chain (dashed line). Hydrogen atoms not involved in hydrogen bonding (dashed lines) are omitted for clarity.

Morpholin-4-ium 4-methoxybenzoate 4-methoxybenzoic acid monohydrate top

Crystal data top

C₄H₁₀NO⁺·C₈H₇O₃⁻·C₈H₈O₃·H₂O	F(000) = 872
M_r = 409.43	D_x = 1.287 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4842 reflections
a = 21.874 (4) Å	θ = 3.0–27.5°
b = 11.753 (2) Å	µ = 0.10 mm⁻¹
c = 8.3618 (17) Å	T = 298 K
β = 100.63 (3)°	Needle, colourless
V = 2112.9 (7) Å³	0.30 × 0.05 × 0.05 mm
Z = 4

Data collection top

Rigaku Mercury2 diffractometer	4842 independent reflections
Radiation source: fine-focus sealed tube	2453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD profile fitting scans	h = −28→27
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
T_min = 0.910, T_max = 1.000	l = −10→10
21489 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.058P)² + 0.3115P] where P = (F_o² + 2F_c²)/3
4842 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₄H₁₀NO⁺·C₈H₇O₃⁻·C₈H₈O₃·H₂O	V = 2112.9 (7) Å³
M_r = 409.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.874 (4) Å	µ = 0.10 mm⁻¹
b = 11.753 (2) Å	T = 298 K
c = 8.3618 (17) Å	0.30 × 0.05 × 0.05 mm
β = 100.63 (3)°

Data collection top

Rigaku Mercury2 diffractometer	4842 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2453 reflections with I > 2σ(I)
T_min = 0.910, T_max = 1.000	R_int = 0.077
21489 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.03	Δρ_max = 0.16 e Å⁻³
4842 reflections	Δρ_min = −0.23 e Å⁻³
264 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
O4	0.30003 (8)	0.67567 (15)	0.28036 (19)	0.0575 (5)
C10	0.40047 (10)	0.61009 (19)	0.2544 (3)	0.0400 (5)
O6	0.56764 (7)	0.62620 (15)	0.0900 (2)	0.0653 (5)
C12	0.46359 (11)	0.6996 (2)	0.0826 (3)	0.0517 (6)
H12A	0.4682	0.7552	0.0067	0.062*
C14	0.50318 (12)	0.5405 (2)	0.2459 (3)	0.0556 (7)
H14A	0.5350	0.4887	0.2807	0.067*
C13	0.51084 (11)	0.6245 (2)	0.1353 (3)	0.0452 (6)
O5	0.34193 (10)	0.53418 (18)	0.4368 (3)	0.0845 (7)
C15	0.44880 (12)	0.5339 (2)	0.3038 (3)	0.0497 (6)
H15A	0.4441	0.4771	0.3780	0.060*
C11	0.40899 (11)	0.6921 (2)	0.1430 (3)	0.0486 (6)
H11A	0.3772	0.7438	0.1075	0.058*
C9	0.34312 (12)	0.6061 (2)	0.3279 (3)	0.0493 (6)
C16	0.57873 (13)	0.7102 (3)	−0.0241 (4)	0.0756 (9)
H16A	0.6193	0.6990	−0.0499	0.113*
H16B	0.5765	0.7846	0.0221	0.113*
H16C	0.5479	0.7038	−0.1215	0.113*
O1W	0.23075 (8)	0.74295 (15)	0.5012 (2)	0.0634 (5)
H1WA	0.2490	0.7132	0.4346	0.095*
H1WB	0.2567	0.7703	0.5746	0.095*
N1	0.26721 (9)	0.00361 (15)	0.1437 (2)	0.0462 (5)
H1A	0.2883	−0.0209	0.0674	0.055*
H1B	0.2299	−0.0308	0.1336	0.055*
O1	0.11518 (8)	−0.23024 (16)	0.0259 (2)	0.0703 (6)
H1	0.1514	−0.2296	0.0125	0.105*
O7	0.26402 (9)	0.14332 (16)	0.4181 (2)	0.0696 (6)
C1	0.10461 (12)	−0.1389 (2)	0.1073 (3)	0.0526 (6)
C2	0.04022 (11)	−0.1286 (2)	0.1359 (3)	0.0469 (6)
O2	0.14422 (8)	−0.06853 (17)	0.1541 (3)	0.0785 (6)
C5	−0.08025 (12)	−0.0989 (2)	0.1886 (3)	0.0550 (7)
O3	−0.14078 (8)	−0.09074 (17)	0.2062 (3)	0.0777 (6)
C7	0.02520 (12)	−0.0385 (2)	0.2269 (3)	0.0587 (7)
H7A	0.0560	0.0130	0.2708	0.070*
C4	−0.06580 (12)	−0.1890 (2)	0.0972 (4)	0.0661 (8)
H4A	−0.0968	−0.2402	0.0528	0.079*
C6	−0.03452 (12)	−0.0231 (2)	0.2543 (3)	0.0594 (7)
H6A	−0.0438	0.0378	0.3167	0.071*
C3	−0.00622 (11)	−0.2043 (2)	0.0707 (3)	0.0571 (7)
H3A	0.0029	−0.2657	0.0089	0.069*
C19	0.30232 (12)	−0.0252 (2)	0.3071 (3)	0.0533 (7)
H19A	0.3443	0.0047	0.3197	0.064*
H19B	0.3050	−0.1072	0.3196	0.064*
C18	0.25775 (15)	0.1276 (2)	0.1291 (3)	0.0706 (8)
H18A	0.2314	0.1452	0.0255	0.085*
H18B	0.2975	0.1652	0.1328	0.085*
C20	0.27063 (14)	0.0242 (2)	0.4338 (3)	0.0671 (8)
H20A	0.2298	−0.0101	0.4253	0.081*
H20B	0.2944	0.0063	0.5405	0.081*
C8	−0.15903 (14)	0.0060 (3)	0.2886 (4)	0.0879 (10)
H8A	−0.2034	0.0060	0.2798	0.132*
H8B	−0.1463	0.0740	0.2404	0.132*
H8C	−0.1396	0.0030	0.4013	0.132*
C17	0.22811 (15)	0.1700 (2)	0.2644 (4)	0.0769 (9)
H17A	0.2230	0.2518	0.2550	0.092*
H17B	0.1872	0.1362	0.2555	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0538 (11)	0.0730 (12)	0.0469 (10)	0.0087 (10)	0.0126 (8)	0.0003 (9)
C10	0.0456 (14)	0.0418 (13)	0.0326 (12)	−0.0019 (11)	0.0079 (11)	−0.0025 (10)
O6	0.0477 (11)	0.0712 (13)	0.0804 (13)	0.0108 (9)	0.0210 (10)	0.0273 (10)
C12	0.0467 (15)	0.0578 (16)	0.0495 (14)	0.0032 (12)	0.0063 (12)	0.0211 (12)
C14	0.0563 (16)	0.0518 (16)	0.0604 (16)	0.0163 (13)	0.0155 (14)	0.0141 (13)
C13	0.0406 (14)	0.0485 (15)	0.0465 (14)	0.0004 (11)	0.0082 (11)	0.0052 (12)
O5	0.0960 (16)	0.0856 (15)	0.0870 (15)	0.0203 (12)	0.0561 (13)	0.0340 (12)
C15	0.0636 (17)	0.0413 (14)	0.0459 (14)	0.0051 (12)	0.0146 (13)	0.0096 (11)
C11	0.0451 (15)	0.0513 (15)	0.0478 (14)	0.0083 (11)	0.0042 (12)	0.0115 (12)
C9	0.0592 (17)	0.0516 (16)	0.0387 (14)	−0.0028 (13)	0.0132 (13)	−0.0047 (12)
C16	0.0621 (19)	0.076 (2)	0.095 (2)	0.0011 (15)	0.0328 (17)	0.0317 (18)
O1W	0.0488 (10)	0.0806 (14)	0.0636 (12)	−0.0085 (9)	0.0179 (9)	−0.0138 (10)
N1	0.0494 (12)	0.0429 (11)	0.0500 (12)	−0.0063 (9)	0.0189 (10)	−0.0085 (9)
O1	0.0494 (11)	0.0678 (13)	0.0960 (15)	−0.0007 (9)	0.0197 (10)	−0.0159 (11)
O7	0.0921 (15)	0.0609 (13)	0.0555 (12)	0.0106 (10)	0.0132 (10)	−0.0171 (10)
C1	0.0443 (15)	0.0538 (17)	0.0588 (16)	0.0016 (13)	0.0075 (13)	0.0077 (13)
C2	0.0421 (14)	0.0471 (15)	0.0507 (14)	−0.0015 (11)	0.0061 (12)	0.0062 (12)
O2	0.0450 (11)	0.0735 (14)	0.1168 (17)	−0.0146 (10)	0.0145 (11)	−0.0202 (12)
C5	0.0444 (15)	0.0568 (17)	0.0662 (17)	−0.0019 (13)	0.0165 (13)	0.0060 (14)
O3	0.0516 (12)	0.0812 (14)	0.1071 (16)	−0.0047 (10)	0.0327 (11)	−0.0130 (12)
C7	0.0471 (16)	0.0622 (17)	0.0655 (17)	−0.0077 (13)	0.0070 (14)	−0.0077 (14)
C4	0.0475 (16)	0.0589 (18)	0.092 (2)	−0.0117 (13)	0.0143 (15)	−0.0122 (16)
C6	0.0594 (18)	0.0560 (17)	0.0636 (17)	−0.0009 (13)	0.0137 (14)	−0.0081 (13)
C3	0.0474 (16)	0.0486 (15)	0.0761 (19)	−0.0017 (12)	0.0137 (14)	−0.0067 (13)
C19	0.0523 (15)	0.0430 (14)	0.0625 (17)	0.0021 (12)	0.0051 (13)	−0.0009 (12)
C18	0.110 (2)	0.0468 (17)	0.0551 (17)	0.0088 (16)	0.0145 (17)	0.0071 (13)
C20	0.091 (2)	0.065 (2)	0.0461 (15)	0.0022 (16)	0.0145 (15)	0.0004 (14)
C8	0.069 (2)	0.108 (3)	0.095 (2)	0.0141 (19)	0.0372 (19)	−0.009 (2)
C17	0.097 (2)	0.0520 (17)	0.079 (2)	0.0267 (16)	0.0081 (18)	−0.0102 (15)

Geometric parameters (Å, º) top

O4—C9	1.256 (3)	C1—O2	1.209 (3)
C10—C11	1.377 (3)	C1—C2	1.476 (3)
C10—C15	1.389 (3)	C2—C7	1.379 (3)
C10—C9	1.496 (3)	C2—C3	1.384 (3)
O6—C13	1.364 (3)	C5—O3	1.362 (3)
O6—C16	1.425 (3)	C5—C6	1.376 (3)
C12—C13	1.369 (3)	C5—C4	1.377 (4)
C12—C11	1.383 (3)	O3—C8	1.424 (3)
C12—H12A	0.9300	C7—C6	1.379 (3)
C14—C15	1.367 (3)	C7—H7A	0.9300
C14—C13	1.384 (3)	C4—C3	1.374 (3)
C14—H14A	0.9300	C4—H4A	0.9300
O5—C9	1.246 (3)	C6—H6A	0.9300
C15—H15A	0.9300	C3—H3A	0.9300
C11—H11A	0.9300	C19—C20	1.487 (3)
C16—H16A	0.9600	C19—H19A	0.9700
C16—H16B	0.9600	C19—H19B	0.9700
C16—H16C	0.9600	C18—C17	1.490 (4)
O1W—H1WA	0.8204	C18—H18A	0.9700
O1W—H1WB	0.8203	C18—H18B	0.9700
N1—C18	1.474 (3)	C20—H20A	0.9700
N1—C19	1.478 (3)	C20—H20B	0.9700
N1—H1A	0.9004	C8—H8A	0.9600
N1—H1B	0.9004	C8—H8B	0.9600
O1—C1	1.315 (3)	C8—H8C	0.9600
O1—H1	0.8206	C17—H17A	0.9700
O7—C20	1.411 (3)	C17—H17B	0.9700
O7—C17	1.412 (3)

C11—C10—C15	117.5 (2)	C6—C5—C4	119.7 (2)
C11—C10—C9	121.9 (2)	C5—O3—C8	118.2 (2)
C15—C10—C9	120.5 (2)	C2—C7—C6	121.5 (2)
C13—O6—C16	118.19 (19)	C2—C7—H7A	119.3
C13—C12—C11	119.6 (2)	C6—C7—H7A	119.3
C13—C12—H12A	120.2	C3—C4—C5	120.8 (2)
C11—C12—H12A	120.2	C3—C4—H4A	119.6
C15—C14—C13	119.9 (2)	C5—C4—H4A	119.6
C15—C14—H14A	120.1	C5—C6—C7	119.3 (2)
C13—C14—H14A	120.1	C5—C6—H6A	120.3
O6—C13—C12	125.0 (2)	C7—C6—H6A	120.3
O6—C13—C14	115.1 (2)	C4—C3—C2	120.1 (2)
C12—C13—C14	119.8 (2)	C4—C3—H3A	120.0
C14—C15—C10	121.5 (2)	C2—C3—H3A	120.0
C14—C15—H15A	119.2	N1—C19—C20	109.8 (2)
C10—C15—H15A	119.2	N1—C19—H19A	109.7
C10—C11—C12	121.7 (2)	C20—C19—H19A	109.7
C10—C11—H11A	119.1	N1—C19—H19B	109.7
C12—C11—H11A	119.1	C20—C19—H19B	109.7
O5—C9—O4	123.9 (2)	H19A—C19—H19B	108.2
O5—C9—C10	117.0 (2)	N1—C18—C17	110.0 (2)
O4—C9—C10	119.1 (2)	N1—C18—H18A	109.7
O6—C16—H16A	109.5	C17—C18—H18A	109.7
O6—C16—H16B	109.5	N1—C18—H18B	109.7
H16A—C16—H16B	109.5	C17—C18—H18B	109.7
O6—C16—H16C	109.5	H18A—C18—H18B	108.2
H16A—C16—H16C	109.5	O7—C20—C19	112.0 (2)
H16B—C16—H16C	109.5	O7—C20—H20A	109.2
H1WA—O1W—H1WB	108.6	C19—C20—H20A	109.2
C18—N1—C19	110.12 (19)	O7—C20—H20B	109.2
C18—N1—H1A	109.9	C19—C20—H20B	109.2
C19—N1—H1A	109.6	H20A—C20—H20B	107.9
C18—N1—H1B	109.0	O3—C8—H8A	109.5
C19—N1—H1B	106.9	O3—C8—H8B	109.5
H1A—N1—H1B	111.3	H8A—C8—H8B	109.5
C1—O1—H1	109.2	O3—C8—H8C	109.5
C20—O7—C17	109.6 (2)	H8A—C8—H8C	109.5
O2—C1—O1	122.8 (2)	H8B—C8—H8C	109.5
O2—C1—C2	122.7 (3)	O7—C17—C18	111.7 (2)
O1—C1—C2	114.5 (2)	O7—C17—H17A	109.3
C7—C2—C3	118.6 (2)	C18—C17—H17A	109.3
C7—C2—C1	118.9 (2)	O7—C17—H17B	109.3
C3—C2—C1	122.4 (2)	C18—C17—H17B	109.3
O3—C5—C6	124.1 (2)	H17A—C17—H17B	107.9
O3—C5—C4	116.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.90	1.75	2.628 (3)	164
N1—H1B···O2	0.90	1.96	2.837 (3)	163
O1—H1···O1Wⁱ	0.82	1.76	2.579 (2)	173
O1W—H1WA···O4	0.82	1.91	2.714 (2)	167
O1W—H1WB···O4ⁱⁱ	0.82	1.91	2.712 (3)	164

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₄H₁₀NO⁺·C₈H₇O₃⁻·C₈H₈O₃·H₂O
M_r	409.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	21.874 (4), 11.753 (2), 8.3618 (17)
β (°)	100.63 (3)
V (Å³)	2112.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.05 × 0.05

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.910, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21489, 4842, 2453
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.162, 1.03
No. of reflections	4842
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.23

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···O5ⁱ	0.90	1.75	2.628 (3)	164
N1—H1B···O2	0.90	1.96	2.837 (3)	163
O1—H1···O1Wⁱ	0.82	1.76	2.579 (2)	173
O1W—H1WA···O4	0.82	1.91	2.714 (2)	167
O1W—H1WB···O4ⁱⁱ	0.82	1.91	2.712 (3)	164

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z+1/2.

Acknowledgements

This work was supported by the start-up fund of Anyang Institute of Technology.

References

Aminabhavi, T. M., Biradar, N. S. & Patil, S. B. (1986). Inorg. Chim. Acta, 125, 125–128. CrossRef CAS Web of Science Google Scholar
Fu, D.-W., Dai, J., Ge, J.-Z., Ye, H.-Y. & Qu, Z.-R. (2010). Inorg. Chem. Commun. 13, 282-285. Web of Science CSD CrossRef 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