4-[1-Acetyl-3-(4-methoxy­phen­yl)-2-pyrazolin-5-yl]phenol

Bai, X.; Chen, H.; Zhang, K.; Li, Y.; Yin, S.

doi:10.1107/S1600536809043785

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2873

https://doi.org/10.1107/S1600536809043785

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4-[1-Acetyl-3-(4-methoxyphenyl)-2-pyrazolin-5-yl]phenol

Xue Bai,^a Hua-feng Chen,^a Kuan Zhang,^a Ying Li ^a and Shu-fan Yin ^a ^*

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: chuandayouji217@163.com

(Received 10 October 2009; accepted 22 October 2009; online 28 October 2009)

In the title compound, C₁₈H₁₈N₂O₃, the dihedral angle formed by the benzene rings is 71.75 (4)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular O—H⋯O hydrogen bonds and π–π stacking interactions with centroid–centroid distances of 3.5511 (6) Å.

Related literature

For the biological activity of 2-pyrazoline derivatives, see: Grimm et al. (2009 ). For the synthesis and crystal structure of 2-pyrazoline derivatives, see: Chen et al. (2009 ); Li et al. (2008 ); Humaira et al. (2008 ); Shoman et al. (2009 ).

Experimental

Crystal data

C₁₈H₁₈N₂O₃
M_r = 310.34
Monoclinic, P 2₁ /n
a = 8.7037 (17) Å
b = 15.673 (3) Å
c = 11.096 (2) Å
β = 100.31 (3)°
V = 1489.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.28 × 0.25 × 0.23 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.974, T_max = 0.978
12107 measured reflections
3542 independent reflections
2857 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.107
S = 1.07
3542 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.84	1.87	2.7117 (13)	175
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809043785/rz2374sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043785/rz2374Isup2.hkl

checkCIF report

Comment top

The 2-pyrazoline ring system has attracted significant interest in organic and medicinal chemistry over the past several decades. Scaffolds containing the 2-pyrazoline (4,5-dihydropyrazole) heterocycle have demonstrated a wide range of biological activity, including anticancer activity through the inhibition of kinesin spindle protein, CB1 receptor antagonism for obesity, monoamine oxidase inhibition for depression, and a host of other antibacterial, antiviral, and anti-inflammatory activities (Grimm et al., 2009). Some crystal structure of pyrazoline derivatives have been recently reported (Chen et al., 2009; Li et al., 2008). The synthesis and characterization of pyrazoline derivatives was also reported (Humaira et al., 2008; Shoman et al., 2009).

In the molecule of the title compound (Fig. 1), the five-membered 2-pyrazoline ring assumes an envelope conformation, with atom C7 displaced by 0.2690 (11) Å from the mean plane of the N1/N2/C8/C9 atoms. The benzene rings form a dihedral angle of 108.25 (4)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular O—H···.O hydrogen bonds (Table 1) and by a π–π stacking interaction involving the C1–C6 aromatic rings, with a centroid-to-centroid distance of 3.5511 (6) Å.

Related literature top

For the biological activity of 2-pyrazoline derivatives, see: Grimm et al. (2009). For the synthesis and crystal structure of 2-pyrazoline derivatives, see: Chen et al. (2009); Li et al. (2008); Humaira et al. (2008); Shoman et al. (2009).

Experimental top

A mixture of 4'-methoxy-4-hydroxychalcone (0.64 g,2.5 mmol) and hydrazine hydrate (1 ml) in acetic acid (15 ml) was refluxed for 2 h. The reaction mixture was then cooled at room temperature, and poured into ice-cold water. The light yellow solid obtained was filtered, washed with water, dichloromethane, and dried. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone/dichloromethane (3:1 v/v) solution at room temperature.

Structure description top

For the biological activity of 2-pyrazoline derivatives, see: Grimm et al. (2009). For the synthesis and crystal structure of 2-pyrazoline derivatives, see: Chen et al. (2009); Li et al. (2008); Humaira et al. (2008); Shoman et al. (2009).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

4-[1-Acetyl-3-(4-methoxyphenyl)-2-pyrazolin-5-yl]phenol top

Crystal data top

C₁₈H₁₈N₂O₃	F(000) = 656
M_r = 310.34	D_x = 1.384 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4953 reflections
a = 8.7037 (17) Å	θ = 1.9–27.9°
b = 15.673 (3) Å	µ = 0.10 mm⁻¹
c = 11.096 (2) Å	T = 113 K
β = 100.31 (3)°	Block, colourless
V = 1489.2 (5) Å³	0.28 × 0.25 × 0.23 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3542 independent reflections
Radiation source: rotating anode	2857 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.035
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.3°
ω and φ scans	h = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −20→20
T_min = 0.974, T_max = 0.978	l = −10→14
12107 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0618P)² + 0.155P] where P = (F_o² + 2F_c²)/3
3542 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₈N₂O₃	V = 1489.2 (5) Å³
M_r = 310.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7037 (17) Å	µ = 0.10 mm⁻¹
b = 15.673 (3) Å	T = 113 K
c = 11.096 (2) Å	0.28 × 0.25 × 0.23 mm
β = 100.31 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3542 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2857 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.978	R_int = 0.035
12107 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.07	Δρ_max = 0.28 e Å⁻³
3542 reflections	Δρ_min = −0.22 e Å⁻³
211 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 > 2σ(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
O1	0.94883 (10)	0.38855 (6)	0.70894 (7)	0.0229 (2)
H1	1.0433	0.3749	0.7160	0.034*
O2	0.75176 (10)	0.66339 (5)	0.27990 (7)	0.0225 (2)
O3	−0.11026 (10)	0.27148 (5)	−0.04411 (8)	0.0231 (2)
N1	0.58975 (11)	0.55520 (6)	0.21083 (8)	0.0167 (2)
N2	0.43790 (11)	0.52531 (6)	0.17203 (8)	0.0171 (2)
C1	0.89186 (13)	0.40973 (7)	0.59032 (10)	0.0168 (2)
C2	0.75202 (13)	0.45422 (7)	0.56538 (10)	0.0182 (2)
H2	0.6974	0.4675	0.6298	0.022*
C3	0.69165 (13)	0.47942 (7)	0.44593 (10)	0.0168 (2)
H3	0.5958	0.5099	0.4295	0.020*
C4	0.77000 (13)	0.46058 (7)	0.35034 (9)	0.0151 (2)
C5	0.90875 (13)	0.41512 (7)	0.37684 (10)	0.0163 (2)
H5	0.9631	0.4015	0.3123	0.020*
C6	0.97009 (13)	0.38908 (7)	0.49508 (10)	0.0164 (2)
H6	1.0646	0.3574	0.5111	0.020*
C7	0.70776 (13)	0.48686 (7)	0.21887 (10)	0.0159 (2)
H7	0.7957	0.5053	0.1780	0.019*
C8	0.61163 (13)	0.41600 (7)	0.14272 (10)	0.0171 (2)
H8A	0.6386	0.4113	0.0600	0.021*
H8B	0.6277	0.3600	0.1843	0.021*
C9	0.44632 (13)	0.44749 (7)	0.13665 (9)	0.0160 (2)
C10	0.61741 (14)	0.63762 (7)	0.24368 (9)	0.0179 (2)
C11	0.47757 (15)	0.69509 (8)	0.23326 (11)	0.0233 (3)
H11A	0.5121	0.7537	0.2534	0.035*
H11B	0.4107	0.6759	0.2903	0.035*
H11C	0.4186	0.6931	0.1493	0.035*
C12	0.30403 (13)	0.39938 (7)	0.09013 (9)	0.0163 (2)
C13	0.31003 (14)	0.31987 (7)	0.03532 (10)	0.0183 (2)
H13	0.4088	0.2956	0.0306	0.022*
C14	0.17471 (14)	0.27499 (7)	−0.01279 (10)	0.0191 (2)
H14	0.1812	0.2213	−0.0512	0.023*
C15	0.03036 (13)	0.30954 (7)	−0.00400 (10)	0.0180 (2)
C16	0.02255 (14)	0.38880 (7)	0.05220 (10)	0.0205 (3)
H16	−0.0763	0.4123	0.0584	0.025*
C17	0.15651 (14)	0.43316 (8)	0.09871 (10)	0.0199 (2)
H17	0.1494	0.4869	0.1369	0.024*
C18	−0.11105 (16)	0.19636 (9)	−0.11600 (13)	0.0320 (3)
H18A	−0.0643	0.2087	−0.1881	0.048*
H18B	−0.2188	0.1769	−0.1424	0.048*
H18C	−0.0506	0.1516	−0.0671	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0209 (5)	0.0314 (5)	0.0155 (4)	0.0013 (4)	0.0014 (3)	0.0053 (3)
O2	0.0226 (5)	0.0219 (4)	0.0217 (4)	−0.0016 (3)	0.0006 (3)	0.0008 (3)
O3	0.0177 (4)	0.0242 (4)	0.0269 (4)	−0.0011 (3)	0.0027 (3)	−0.0048 (3)
N1	0.0146 (5)	0.0173 (5)	0.0179 (4)	0.0021 (4)	0.0021 (4)	0.0011 (3)
N2	0.0161 (5)	0.0191 (5)	0.0158 (4)	0.0003 (4)	0.0021 (4)	0.0015 (4)
C1	0.0174 (6)	0.0167 (5)	0.0158 (5)	−0.0046 (4)	0.0017 (4)	0.0015 (4)
C2	0.0174 (6)	0.0216 (6)	0.0165 (5)	−0.0023 (4)	0.0058 (4)	−0.0007 (4)
C3	0.0133 (5)	0.0182 (5)	0.0190 (5)	0.0000 (4)	0.0035 (4)	−0.0002 (4)
C4	0.0156 (5)	0.0144 (5)	0.0150 (5)	−0.0021 (4)	0.0022 (4)	0.0001 (4)
C5	0.0174 (6)	0.0155 (5)	0.0168 (5)	−0.0007 (4)	0.0054 (4)	−0.0013 (4)
C6	0.0141 (6)	0.0147 (5)	0.0201 (5)	−0.0002 (4)	0.0020 (4)	0.0008 (4)
C7	0.0154 (5)	0.0172 (5)	0.0155 (5)	0.0033 (4)	0.0040 (4)	0.0002 (4)
C8	0.0170 (6)	0.0193 (5)	0.0148 (5)	0.0024 (4)	0.0023 (4)	−0.0011 (4)
C9	0.0177 (6)	0.0187 (5)	0.0118 (5)	0.0037 (4)	0.0030 (4)	0.0018 (4)
C10	0.0229 (6)	0.0177 (5)	0.0134 (5)	0.0007 (5)	0.0037 (4)	0.0021 (4)
C11	0.0261 (6)	0.0176 (5)	0.0260 (6)	0.0033 (5)	0.0046 (5)	−0.0011 (5)
C12	0.0176 (6)	0.0186 (5)	0.0128 (5)	0.0017 (4)	0.0027 (4)	0.0022 (4)
C13	0.0174 (6)	0.0196 (5)	0.0184 (5)	0.0042 (4)	0.0043 (4)	0.0007 (4)
C14	0.0216 (6)	0.0171 (5)	0.0183 (5)	0.0021 (4)	0.0030 (4)	−0.0009 (4)
C15	0.0179 (6)	0.0212 (6)	0.0146 (5)	0.0003 (4)	0.0019 (4)	0.0029 (4)
C16	0.0177 (6)	0.0230 (6)	0.0212 (5)	0.0041 (5)	0.0047 (4)	−0.0009 (4)
C17	0.0210 (6)	0.0202 (5)	0.0188 (5)	0.0041 (5)	0.0040 (4)	−0.0017 (4)
C18	0.0253 (7)	0.0251 (6)	0.0435 (8)	−0.0009 (5)	0.0008 (6)	−0.0114 (6)

Geometric parameters (Å, º) top

O1—C1	1.3619 (13)	C8—C9	1.5112 (15)
O1—H1	0.8400	C8—H8A	0.9900
O2—C10	1.2345 (15)	C8—H8B	0.9900
O3—C15	1.3626 (14)	C9—C12	1.4628 (16)
O3—C18	1.4216 (15)	C10—C11	1.5018 (16)
N1—C10	1.3521 (15)	C11—H11A	0.9800
N1—N2	1.3957 (13)	C11—H11B	0.9800
N1—C7	1.4757 (14)	C11—H11C	0.9800
N2—C9	1.2873 (14)	C12—C13	1.3917 (15)
C1—C2	1.3870 (16)	C12—C17	1.4077 (16)
C1—C6	1.3939 (15)	C13—C14	1.3935 (16)
C2—C3	1.3927 (16)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.3875 (16)
C3—C4	1.3915 (15)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.3970 (16)
C4—C5	1.3876 (16)	C16—C17	1.3762 (17)
C4—C7	1.5193 (15)	C16—H16	0.9500
C5—C6	1.3865 (15)	C17—H17	0.9500
C5—H5	0.9500	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C7—C8	1.5474 (16)	C18—H18C	0.9800
C7—H7	1.0000

C1—O1—H1	109.5	N2—C9—C12	120.34 (10)
C15—O3—C18	117.37 (9)	N2—C9—C8	113.68 (10)
C10—N1—N2	121.13 (9)	C12—C9—C8	125.91 (10)
C10—N1—C7	126.07 (10)	O2—C10—N1	120.86 (10)
N2—N1—C7	112.67 (9)	O2—C10—C11	122.43 (10)
C9—N2—N1	108.04 (9)	N1—C10—C11	116.71 (10)
O1—C1—C2	118.04 (10)	C10—C11—H11A	109.5
O1—C1—C6	122.24 (10)	C10—C11—H11B	109.5
C2—C1—C6	119.72 (10)	H11A—C11—H11B	109.5
C1—C2—C3	120.04 (10)	C10—C11—H11C	109.5
C1—C2—H2	120.0	H11A—C11—H11C	109.5
C3—C2—H2	120.0	H11B—C11—H11C	109.5
C4—C3—C2	120.82 (10)	C13—C12—C17	118.18 (11)
C4—C3—H3	119.6	C13—C12—C9	121.34 (10)
C2—C3—H3	119.6	C17—C12—C9	120.47 (10)
C5—C4—C3	118.30 (10)	C12—C13—C14	121.61 (10)
C5—C4—C7	119.33 (9)	C12—C13—H13	119.2
C3—C4—C7	122.36 (10)	C14—C13—H13	119.2
C6—C5—C4	121.65 (10)	C15—C14—C13	119.34 (10)
C6—C5—H5	119.2	C15—C14—H14	120.3
C4—C5—H5	119.2	C13—C14—H14	120.3
C5—C6—C1	119.44 (10)	O3—C15—C14	125.30 (11)
C5—C6—H6	120.3	O3—C15—C16	114.99 (10)
C1—C6—H6	120.3	C14—C15—C16	119.69 (11)
N1—C7—C4	112.31 (9)	C17—C16—C15	120.73 (11)
N1—C7—C8	100.69 (9)	C17—C16—H16	119.6
C4—C7—C8	113.25 (9)	C15—C16—H16	119.6
N1—C7—H7	110.1	C16—C17—C12	120.42 (11)
C4—C7—H7	110.1	C16—C17—H17	119.8
C8—C7—H7	110.1	C12—C17—H17	119.8
C9—C8—C7	101.97 (9)	O3—C18—H18A	109.5
C9—C8—H8A	111.4	O3—C18—H18B	109.5
C7—C8—H8A	111.4	H18A—C18—H18B	109.5
C9—C8—H8B	111.4	O3—C18—H18C	109.5
C7—C8—H8B	111.4	H18A—C18—H18C	109.5
H8A—C8—H8B	109.2	H18B—C18—H18C	109.5

C10—N1—N2—C9	174.49 (9)	N1—N2—C9—C8	−2.58 (12)
C7—N1—N2—C9	−9.40 (11)	C7—C8—C9—N2	12.40 (12)
O1—C1—C2—C3	178.11 (10)	C7—C8—C9—C12	−170.70 (9)
C6—C1—C2—C3	−1.14 (16)	N2—N1—C10—O2	178.76 (9)
C1—C2—C3—C4	−0.03 (17)	C7—N1—C10—O2	3.20 (16)
C2—C3—C4—C5	0.80 (16)	N2—N1—C10—C11	−1.45 (14)
C2—C3—C4—C7	179.90 (10)	C7—N1—C10—C11	−177.02 (9)
C3—C4—C5—C6	−0.41 (16)	N2—C9—C12—C13	170.72 (10)
C7—C4—C5—C6	−179.55 (10)	C8—C9—C12—C13	−5.99 (16)
C4—C5—C6—C1	−0.73 (16)	N2—C9—C12—C17	−8.61 (15)
O1—C1—C6—C5	−177.70 (10)	C8—C9—C12—C17	174.68 (10)
C2—C1—C6—C5	1.51 (16)	C17—C12—C13—C14	1.49 (16)
C10—N1—C7—C4	71.36 (13)	C9—C12—C13—C14	−177.86 (10)
N2—N1—C7—C4	−104.52 (10)	C12—C13—C14—C15	−1.19 (16)
C10—N1—C7—C8	−167.87 (10)	C18—O3—C15—C14	−9.49 (16)
N2—N1—C7—C8	16.25 (10)	C18—O3—C15—C16	171.96 (10)
C5—C4—C7—N1	−162.58 (9)	C13—C14—C15—O3	−178.16 (10)
C3—C4—C7—N1	18.32 (15)	C13—C14—C15—C16	0.33 (16)
C5—C4—C7—C8	84.19 (12)	O3—C15—C16—C17	178.82 (10)
C3—C4—C7—C8	−94.91 (12)	C14—C15—C16—C17	0.18 (17)
N1—C7—C8—C9	−15.77 (10)	C15—C16—C17—C12	0.15 (17)
C4—C7—C8—C9	104.33 (10)	C13—C12—C17—C16	−0.96 (16)
N1—N2—C9—C12	−179.67 (8)	C9—C12—C17—C16	178.39 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.87	2.7117 (13)	175

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂O₃
M_r	310.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	8.7037 (17), 15.673 (3), 11.096 (2)
β (°)	100.31 (3)
V (Å³)	1489.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.28 × 0.25 × 0.23

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.974, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	12107, 3542, 2857
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.107, 1.07
No. of reflections	3542
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.22

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.87	2.7117 (13)	174.5

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

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