3-(1-Naphth­yl)-N-phenyl­oxirane-2-carboxamide

Chen, L.-M.; Kang, T.-R.

doi:10.1107/S1600536809048752

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3137

doi:10.1107/S1600536809048752

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3-(1-Naphthyl)-N-phenyloxirane-2-carboxamide

Lian-Mei Chen ^a and Tai-Ran Kang ^a ^*

^aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: kangtairan@yahoo.com.cn

(Received 16 November 2009; accepted 16 November 2009; online 21 November 2009)

In the title compound, C₁₉H₁₅NO₂, the molecule adopts a syn configuration with the naphthalene and N-phenylformamide units located on the same side of the epoxy ring. The epoxy ring makes dihedral angles of 58.73 (9) and 65.18 (9)°, respectively, with the naphthalene ring system and the benzene ring. Intermolecular N—H⋯O and C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For background to the use of epoxide-containing compounds as building blocks in the synthesis of biologically active compounds, see: Porter & Skidmore (2000 ); Shing et al. (2006 ); Watanabe et al. (1998 ). For related structures, see: He (2009 ); He & Chen (2009 ); He et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₅NO₂
M_r = 289.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.62890 (10) Å
b = 10.03500 (10) Å
c = 23.2033 (3) Å
V = 1543.51 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.65 mm⁻¹
T = 290 K
0.40 × 0.36 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.782, T_max = 0.829
13761 measured reflections
1783 independent reflections
1641 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.093
S = 1.08
1783 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.08 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H4⋯O2ⁱ	0.84 (2)	2.17 (2)	2.954 (1)	155.7 (18)
C5—H5⋯O1ⁱⁱ	0.93	2.58	3.431 (2)	153 (1)
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048752/xu2678sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048752/xu2678Isup2.hkl

checkCIF report

Comment top

α,β-Epoxides are very important building blocks for the synthesis of complex molecules, in particular, of biologically active compounds (Porter & Skidmore, 2000; Shing et al., 2006; Watanabe et al., 1998). Various effective systems have been developed over the years for the preparation of α,β-epoxides. The most common approach to access these molecules is the epoxidation of α,β-unsaturatd carbonyl compound. As a part of our interest in the synthsis of epoxides ring systems, we synthesis the title compound by using Darzens reaction. We report herein the crystal structure of the title compound.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. In the molecular, the 1-naphthyl ring with the phenyl ring adopts a cis configuration about the epoxides ring. The dihedral angle between the phenyl ring and the 1-naphthyl ring is 77.79 (4)°, O1/C8/C9 epoxide ring makes dihedral angles of 58.73 (9)° and 65.18 (9)° with the 1-naphthyl ring and phenyl ring, respectively. These values are very similar to those observed in related structures (He, 2009; He & Chen, 2009; He et al., 2009). The crystal packing is stabilized by N—H···0 and C—H···0 hydrogen bonding (Table 1).

Related literature top

For background to the use of epoxide-containing compounds as building blocks in the synthesis of biologically active compounds, see: Porter & Skidmore (2000); Shing et al. (2006); Watanabe et al. (1998). For related structures, see: He (2009); He & Chen (2009); He et al. (2009).

Experimental top

2-Chloro-N-phenylacetamide (0.085 g, 0.5 mmol) and potassium hydroxide (0.056 g, 1.0 mmol) were dissolved in chloroform (4 ml). To the solution was added 1-naphthaldehyde (0.094 g, 0.6 mmol) at 298 K, the solution was stirred for 6 h and removal of solvent under reduced pressure, the residue was purified through column chromatography. Colourless single crystals of (I) were obtained by recrystallization from an ethyl acetate solution.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

3-(1-Naphthyl)-N-phenyloxirane-2-carboxamide top

Crystal data top

C₁₉H₁₅NO₂	F(000) = 608
M_r = 289.32	D_x = 1.245 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9381 reflections
a = 6.6289 (1) Å	θ = 3.8–72.1°
b = 10.0350 (1) Å	µ = 0.65 mm⁻¹
c = 23.2033 (3) Å	T = 290 K
V = 1543.51 (3) Å³	Block, colorless
Z = 4	0.40 × 0.36 × 0.30 mm

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	1783 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1641 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 15.9149 pixels mm^-1	θ_max = 72.3°, θ_min = 3.8°
ω scans	h = −6→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
T_min = 0.782, T_max = 0.829	l = −26→28
13761 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0641P)² + 0.0314P] where P = (F_o² + 2F_c²)/3
1783 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.08 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₉H₁₅NO₂	V = 1543.51 (3) Å³
M_r = 289.32	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 6.6289 (1) Å	µ = 0.65 mm⁻¹
b = 10.0350 (1) Å	T = 290 K
c = 23.2033 (3) Å	0.40 × 0.36 × 0.30 mm

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	1783 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1641 reflections with I > 2σ(I)
T_min = 0.782, T_max = 0.829	R_int = 0.031
13761 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.08 e Å⁻³
1783 reflections	Δρ_min = −0.13 e Å⁻³
203 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
O1	1.20270 (19)	0.10810 (12)	0.82723 (5)	0.0681 (3)
O2	1.0096 (2)	0.38001 (11)	0.74225 (7)	0.0738 (4)
N1	0.8951 (2)	0.16688 (13)	0.74912 (6)	0.0534 (3)
H4	0.926 (3)	0.092 (2)	0.7622 (8)	0.065 (5)*
C1	0.3564 (3)	0.1625 (3)	0.65510 (8)	0.0820 (6)
H1	0.2376	0.1592	0.6339	0.098*
C2	0.4104 (3)	0.0578 (2)	0.68938 (9)	0.0750 (5)
H2	0.3275	−0.0168	0.6917	0.090*
C3	0.5874 (3)	0.06219 (17)	0.72067 (8)	0.0619 (4)
H3	0.6224	−0.0090	0.7443	0.074*
C4	0.7135 (2)	0.17226 (15)	0.71700 (6)	0.0521 (3)
C5	0.6590 (3)	0.27941 (19)	0.68282 (8)	0.0659 (4)
H5	0.7411	0.3543	0.6804	0.079*
C6	0.4786 (3)	0.2728 (2)	0.65216 (9)	0.0806 (6)
H6	0.4402	0.3445	0.6292	0.097*
C7	1.0258 (2)	0.26612 (14)	0.75961 (7)	0.0523 (3)
C8	1.2046 (2)	0.23071 (15)	0.79612 (7)	0.0558 (4)
H8	1.3359	0.2573	0.7805	0.067*
C9	1.1896 (2)	0.23005 (17)	0.85940 (8)	0.0597 (4)
H9	1.3135	0.2555	0.8797	0.072*
C10	0.9999 (3)	0.25565 (18)	0.89182 (7)	0.0588 (4)
C11	0.8539 (3)	0.1600 (2)	0.89662 (8)	0.0738 (5)
H11	0.8689	0.0791	0.8776	0.089*
C12	0.6808 (3)	0.1835 (3)	0.93030 (9)	0.0855 (7)
H12	0.5819	0.1181	0.9330	0.103*
C13	0.6567 (3)	0.2994 (3)	0.95855 (9)	0.0854 (7)
H13	0.5414	0.3127	0.9807	0.103*
C14	0.8028 (3)	0.4013 (2)	0.95534 (7)	0.0718 (5)
C15	0.9780 (3)	0.38002 (19)	0.92061 (7)	0.0587 (4)
C16	1.1212 (3)	0.4825 (2)	0.91701 (8)	0.0690 (4)
H16	1.2345	0.4710	0.8939	0.083*
C17	1.0979 (4)	0.5988 (3)	0.94673 (10)	0.0880 (6)
H17	1.1938	0.6659	0.9432	0.106*
C18	0.9322 (5)	0.6176 (3)	0.98222 (11)	0.1012 (8)
H18	0.9205	0.6956	1.0036	0.121*
C19	0.7874 (4)	0.5231 (3)	0.98595 (9)	0.0927 (7)
H19	0.6752	0.5383	1.0091	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0674 (7)	0.0523 (6)	0.0846 (7)	0.0119 (6)	−0.0146 (6)	−0.0057 (5)
O2	0.0694 (7)	0.0412 (6)	0.1109 (10)	−0.0041 (6)	−0.0195 (7)	0.0016 (6)
N1	0.0506 (7)	0.0396 (6)	0.0700 (7)	−0.0001 (5)	−0.0054 (6)	−0.0003 (6)
C1	0.0604 (10)	0.1084 (17)	0.0771 (11)	0.0011 (11)	−0.0134 (9)	−0.0229 (12)
C2	0.0523 (9)	0.0768 (12)	0.0960 (13)	−0.0071 (9)	0.0031 (9)	−0.0250 (11)
C3	0.0518 (8)	0.0524 (8)	0.0814 (10)	−0.0007 (7)	0.0049 (7)	−0.0099 (8)
C4	0.0486 (8)	0.0488 (7)	0.0590 (8)	0.0025 (7)	0.0020 (6)	−0.0085 (6)
C5	0.0660 (10)	0.0609 (9)	0.0707 (9)	−0.0014 (8)	−0.0075 (8)	0.0042 (8)
C6	0.0768 (12)	0.0928 (14)	0.0722 (11)	0.0095 (12)	−0.0161 (10)	0.0058 (10)
C7	0.0491 (8)	0.0411 (7)	0.0666 (8)	0.0019 (6)	−0.0003 (7)	−0.0092 (6)
C8	0.0455 (7)	0.0464 (7)	0.0754 (9)	0.0041 (7)	−0.0016 (7)	−0.0099 (7)
C9	0.0476 (8)	0.0591 (8)	0.0725 (9)	0.0031 (7)	−0.0106 (7)	−0.0094 (7)
C10	0.0505 (8)	0.0687 (9)	0.0571 (8)	0.0000 (8)	−0.0086 (7)	0.0031 (7)
C11	0.0653 (10)	0.0803 (12)	0.0757 (10)	−0.0129 (10)	−0.0124 (9)	0.0083 (10)
C12	0.0612 (11)	0.1093 (17)	0.0859 (13)	−0.0194 (13)	−0.0057 (10)	0.0263 (13)
C13	0.0564 (11)	0.131 (2)	0.0693 (10)	0.0054 (12)	0.0082 (9)	0.0238 (12)
C14	0.0595 (10)	0.1020 (14)	0.0539 (8)	0.0149 (11)	0.0018 (7)	0.0095 (9)
C15	0.0531 (8)	0.0723 (10)	0.0505 (7)	0.0054 (8)	−0.0034 (6)	0.0030 (7)
C16	0.0660 (10)	0.0751 (11)	0.0658 (9)	−0.0003 (9)	−0.0002 (8)	−0.0080 (9)
C17	0.0988 (16)	0.0799 (13)	0.0853 (12)	−0.0038 (13)	−0.0017 (12)	−0.0181 (11)
C18	0.120 (2)	0.1003 (17)	0.0831 (13)	0.0244 (18)	0.0033 (14)	−0.0278 (13)
C19	0.0897 (15)	0.1226 (19)	0.0658 (10)	0.0355 (16)	0.0118 (11)	−0.0050 (12)

Geometric parameters (Å, º) top

O1—C8	1.4266 (19)	C9—C10	1.488 (2)
O1—C9	1.436 (2)	C9—H9	0.9800
O2—C7	1.217 (2)	C10—C11	1.367 (3)
N1—C7	1.342 (2)	C10—C15	1.423 (2)
N1—C4	1.417 (2)	C11—C12	1.408 (3)
N1—H4	0.84 (2)	C11—H11	0.9300
C1—C2	1.365 (3)	C12—C13	1.345 (4)
C1—C6	1.373 (3)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.410 (3)
C2—C3	1.381 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—C19	1.417 (4)
C3—C4	1.388 (2)	C14—C15	1.429 (2)
C3—H3	0.9300	C15—C16	1.402 (3)
C4—C5	1.384 (2)	C16—C17	1.364 (3)
C5—C6	1.393 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.386 (4)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.499 (2)	C18—C19	1.352 (4)
C8—C9	1.472 (2)	C18—H18	0.9300
C8—H8	0.9800	C19—H19	0.9300

C8—O1—C9	61.87 (10)	O1—C9—H9	114.9
C7—N1—C4	127.99 (14)	C8—C9—H9	114.9
C7—N1—H4	116.1 (15)	C10—C9—H9	114.9
C4—N1—H4	115.8 (15)	C11—C10—C15	120.32 (16)
C2—C1—C6	119.65 (18)	C11—C10—C9	121.23 (17)
C2—C1—H1	120.2	C15—C10—C9	118.36 (15)
C6—C1—H1	120.2	C10—C11—C12	120.3 (2)
C1—C2—C3	120.29 (19)	C10—C11—H11	119.8
C1—C2—H2	119.9	C12—C11—H11	119.8
C3—C2—H2	119.9	C13—C12—C11	120.8 (2)
C2—C3—C4	120.33 (18)	C13—C12—H12	119.6
C2—C3—H3	119.8	C11—C12—H12	119.6
C4—C3—H3	119.8	C12—C13—C14	121.31 (19)
C5—C4—C3	119.75 (15)	C12—C13—H13	119.3
C5—C4—N1	123.56 (15)	C14—C13—H13	119.3
C3—C4—N1	116.68 (14)	C13—C14—C19	123.3 (2)
C4—C5—C6	118.67 (18)	C13—C14—C15	118.65 (19)
C4—C5—H5	120.7	C19—C14—C15	118.0 (2)
C6—C5—H5	120.7	C16—C15—C10	123.11 (16)
C1—C6—C5	121.3 (2)	C16—C15—C14	118.30 (18)
C1—C6—H6	119.4	C10—C15—C14	118.59 (17)
C5—C6—H6	119.4	C17—C16—C15	121.4 (2)
O2—C7—N1	125.45 (15)	C17—C16—H16	119.3
O2—C7—C8	118.66 (14)	C15—C16—H16	119.3
N1—C7—C8	115.89 (13)	C16—C17—C18	120.5 (2)
O1—C8—C9	59.38 (10)	C16—C17—H17	119.8
O1—C8—C7	118.91 (13)	C18—C17—H17	119.8
C9—C8—C7	120.76 (13)	C19—C18—C17	120.4 (2)
O1—C8—H8	115.4	C19—C18—H18	119.8
C9—C8—H8	115.4	C17—C18—H18	119.8
C7—C8—H8	115.4	C18—C19—C14	121.4 (2)
O1—C9—C8	58.75 (10)	C18—C19—H19	119.3
O1—C9—C10	117.46 (15)	C14—C19—H19	119.3
C8—C9—C10	124.10 (14)

C6—C1—C2—C3	−0.4 (3)	O1—C9—C10—C15	−175.59 (13)
C1—C2—C3—C4	−0.8 (3)	C8—C9—C10—C15	−106.34 (18)
C2—C3—C4—C5	1.5 (2)	C15—C10—C11—C12	−0.3 (3)
C2—C3—C4—N1	−178.11 (15)	C9—C10—C11—C12	176.26 (16)
C7—N1—C4—C5	11.2 (2)	C10—C11—C12—C13	−0.5 (3)
C7—N1—C4—C3	−169.22 (16)	C11—C12—C13—C14	0.2 (3)
C3—C4—C5—C6	−0.9 (3)	C12—C13—C14—C19	−177.7 (2)
N1—C4—C5—C6	178.69 (16)	C12—C13—C14—C15	0.8 (3)
C2—C1—C6—C5	1.0 (3)	C11—C10—C15—C16	−179.42 (17)
C4—C5—C6—C1	−0.4 (3)	C9—C10—C15—C16	4.0 (2)
C4—N1—C7—O2	−0.7 (3)	C11—C10—C15—C14	1.2 (2)
C4—N1—C7—C8	179.01 (13)	C9—C10—C15—C14	−175.40 (14)
C9—O1—C8—C7	−110.62 (15)	C13—C14—C15—C16	179.15 (17)
O2—C7—C8—O1	165.96 (15)	C19—C14—C15—C16	−2.3 (2)
N1—C7—C8—O1	−13.7 (2)	C13—C14—C15—C10	−1.5 (2)
O2—C7—C8—C9	96.3 (2)	C19—C14—C15—C10	177.07 (16)
N1—C7—C8—C9	−83.36 (18)	C10—C15—C16—C17	−177.89 (18)
C8—O1—C9—C10	115.07 (16)	C14—C15—C16—C17	1.5 (3)
C7—C8—C9—O1	107.55 (15)	C15—C16—C17—C18	1.1 (4)
O1—C8—C9—C10	−103.91 (18)	C16—C17—C18—C19	−2.7 (4)
C7—C8—C9—C10	3.6 (2)	C17—C18—C19—C14	1.8 (4)
O1—C9—C10—C11	7.8 (2)	C13—C14—C19—C18	179.2 (2)
C8—C9—C10—C11	77.1 (2)	C15—C14—C19—C18	0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O2ⁱ	0.84 (2)	2.17 (2)	2.954 (1)	155.7 (18)
C5—H5···O1ⁱⁱ	0.93	2.58	3.431 (2)	153 (1)

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅NO₂
M_r	289.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	290
a, b, c (Å)	6.6289 (1), 10.0350 (1), 23.2033 (3)
V (Å³)	1543.51 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.40 × 0.36 × 0.30

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.782, 0.829
No. of measured, independent and observed [I > 2σ(I)] reflections	13761, 1783, 1641
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.093, 1.08
No. of reflections	1783
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.08, −0.13

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O2ⁱ	0.84 (2)	2.17 (2)	2.954 (1)	155.7 (18)
C5—H5···O1ⁱⁱ	0.93	2.58	3.431 (2)	152.5 (3)

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

Acknowledgements

The diffraction data were collected at the Centre for Testing and Analysis, Sichuan University. We are grateful for financial support from China West Normal University (No 412374).

References

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