Methyl 2-[2-(6-chloro­pyrimidin-4-yl­oxy)phen­yl]-3,3-dimethoxy­propanoate

Sheng, C.; Xu, Q.-B.; Liu, Y.-Y.; Zhu, H.-J.

doi:10.1107/S1600536809030736

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2117

doi:10.1107/S1600536809030736

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Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate

Chao Sheng,^a Qing-Bing Xu,^a Yuan-Yuan Liu ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 30 July 2009; accepted 3 August 2009; online 8 August 2009)

In the title compound, C₁₆H₁₇ClN₂O₅, the dihedral angle between the aromatic rings is 77.36 (4)°. An intramolecular C—H⋯O interaction results in the formation of a planar [r.m.s. deviation = 0.103 (2) Å] five-membered ring, which is oriented at a dihedral angle of 4.84 (4)° with respect to the adjacent benzene ring. In the crystal structure, weak intermolecular C—H⋯π interactions are found.

Related literature

For a related structure, see: Bowden & Brown (1996 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₇ClN₂O₅
M_r = 352.77
Triclinic, $[P \overline 1]$
a = 9.5030 (19) Å
b = 10.051 (2) Å
c = 11.162 (2) Å
α = 101.24 (3)°
β = 108.47 (3)°
γ = 113.42 (3)°
V = 862.6 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 294 K
0.20 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.952, T_max = 0.988
3346 measured reflections
3140 independent reflections
1427 reflections with I > 2σ(I)
R_int = 0.035
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.173
S = 1.07
3140 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O5	0.98	2.25	2.777 (6)	113
C1—H1B⋯Cg2ⁱ	0.96	2.97	3.696 (5)	134
C16—H16A⋯Cg1ⁱ	0.93	2.85	3.661 (4)	146
Symmetry code: (i) -x+1, -y+1, -z. Cg1 and Cg2 are centroids of the C7–C12 and N1/N2/C13–C16 rings, respectively.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030736/hk2749sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030736/hk2749Isup2.hkl

checkCIF report

Comment top

The title compound can be used as an intermediate in the preparation of azoxystrobin, which is an important fungicide (Bowden & Brown, 1996). We report herein the crystal structure of the title compound, which is of interest to us in the field.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C7-C12) and B (N1/N2/C13-C16) are, of course, planar and the dihedral angle between them is A/B = 77.36 (4)°. Intramolecular C-H···O interaction (Table 1) results in the formation of a planar five-membered ring C (O5/C6-C8/H6A), which is oriented with respect to the adjacent ring A at a dihedral angle of A/C = 4.84 (4)°.

In the crystal structure, weak C—H···π interactions (Table 1) are found.

Related literature top

For a related structure, see: Bowden & Brown (1996). For bond-length data, see: Allen et al. (1987). Cg1 and Cg2 are centroids of the C7–C12 and N1/N2/C13–C16 rings, respectively.

Experimental top

The title compound was prepared acording to a literature method (Bowden & Brown, 1996). Crystals suitable for X-ray analysis were obtained by dissolving the title compound in methanol and evaporating the solvent slowly at room temperature for 8 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bond is shown as dashed line.

Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate top

Crystal data top

C₁₆H₁₇ClN₂O₅	Z = 2
M_r = 352.77	F(000) = 368
Triclinic, P1	D_x = 1.358 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5030 (19) Å	Cell parameters from 25 reflections
b = 10.051 (2) Å	θ = 9–12°
c = 11.162 (2) Å	µ = 0.25 mm⁻¹
α = 101.24 (3)°	T = 294 K
β = 108.47 (3)°	Needle, colorless
γ = 113.42 (3)°	0.20 × 0.20 × 0.05 mm
V = 862.6 (5) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1427 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.3°, θ_min = 2.1°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −12→11
T_min = 0.952, T_max = 0.988	l = −13→12
3346 measured reflections	3 standard reflections every 120 min
3140 independent reflections	intensity decay: 1%

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)] = 0.078	H-atom parameters constrained
wR(F²) = 0.173	w = 1/[σ²(F_o²) + (0.060P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3140 reflections	Δρ_max = 0.43 e Å⁻³
211 parameters	Δρ_min = −0.45 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₆H₁₇ClN₂O₅	γ = 113.42 (3)°
M_r = 352.77	V = 862.6 (5) Å³
Triclinic, P1	Z = 2
a = 9.5030 (19) Å	Mo Kα radiation
b = 10.051 (2) Å	µ = 0.25 mm⁻¹
c = 11.162 (2) Å	T = 294 K
α = 101.24 (3)°	0.20 × 0.20 × 0.05 mm
β = 108.47 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1427 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.035
T_min = 0.952, T_max = 0.988	3 standard reflections every 120 min
3346 measured reflections	intensity decay: 1%
3140 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	211 parameters
wR(F²) = 0.173	H-atom parameters constrained
S = 1.07	Δρ_max = 0.43 e Å⁻³
3140 reflections	Δρ_min = −0.45 e Å⁻³

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
Cl	0.16863 (16)	0.54848 (17)	0.23573 (15)	0.0918 (5)
O1	−0.7131 (4)	0.4178 (4)	−0.3468 (3)	0.0806 (10)
O2	−0.6406 (5)	0.2829 (5)	−0.4869 (4)	0.1119 (14)
O3	−0.5192 (5)	0.0798 (5)	−0.3027 (4)	0.1150 (14)
O4	−0.7857 (7)	−0.0410 (6)	−0.4408 (5)	0.1371 (18)
O5	−0.4458 (3)	0.3794 (3)	−0.0203 (3)	0.0658 (9)
N1	−0.3799 (5)	0.1982 (4)	0.0434 (4)	0.0631 (11)
N2	−0.0880 (5)	0.2702 (5)	0.1614 (4)	0.0727 (11)
C1	−0.8435 (9)	0.4438 (9)	−0.4217 (6)	0.131 (3)
H1B	−0.8231	0.5446	−0.3730	0.196*
H1C	−0.9517	0.3648	−0.4345	0.196*
H1D	−0.8443	0.4398	−0.5086	0.196*
C2	−0.6907 (10)	0.2967 (8)	−0.6060 (6)	0.140 (3)
H2B	−0.6124	0.2972	−0.6432	0.210*
H2C	−0.6938	0.3925	−0.5950	0.210*
H2D	−0.8026	0.2105	−0.6664	0.210*
C3	−0.7194 (7)	0.2788 (5)	−0.4025 (5)	0.0710 (14)
H3A	−0.8400	0.2004	−0.4578	0.085*
C4	−0.5126 (8)	−0.0639 (7)	−0.3384 (6)	0.1142 (16)
H4A	−0.3983	−0.0432	−0.2896	0.171*
H4B	−0.5469	−0.1044	−0.4343	0.171*
H4C	−0.5883	−0.1389	−0.3148	0.171*
C5	−0.6598 (11)	0.0736 (9)	−0.3573 (8)	0.1142 (16)
C6	−0.6513 (6)	0.2253 (6)	−0.2981 (5)	0.0688 (13)
H6A	−0.5298	0.3025	−0.2460	0.083*
C7	−0.7250 (6)	0.2132 (5)	−0.1948 (5)	0.0517 (11)
C8	−0.6183 (5)	0.2823 (4)	−0.0593 (5)	0.0464 (10)
C9	−0.6753 (6)	0.2753 (5)	0.0390 (5)	0.0609 (13)
H9A	−0.5986	0.3259	0.1305	0.073*
C10	−0.8481 (7)	0.1921 (6)	0.0000 (6)	0.0699 (14)
H10A	−0.8884	0.1850	0.0656	0.084*
C11	−0.9602 (6)	0.1202 (6)	−0.1340 (7)	0.0793 (16)
H11A	−1.0770	0.0644	−0.1607	0.095*
C12	−0.8968 (6)	0.1316 (5)	−0.2302 (5)	0.0691 (14)
H12A	−0.9732	0.0823	−0.3218	0.083*
C13	−0.3283 (6)	0.3428 (5)	0.0417 (4)	0.0536 (11)
C14	−0.2533 (6)	0.1731 (5)	0.1042 (5)	0.0720 (14)
H14A	−0.2858	0.0737	0.1068	0.086*
C15	−0.0453 (6)	0.4133 (5)	0.1578 (4)	0.0586 (12)
C16	−0.1620 (5)	0.4550 (5)	0.0963 (4)	0.0575 (12)
H16A	−0.1295	0.5538	0.0923	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0588 (8)	0.0939 (11)	0.1023 (11)	0.0264 (7)	0.0267 (8)	0.0357 (8)
O1	0.104 (3)	0.067 (2)	0.066 (2)	0.047 (2)	0.023 (2)	0.0268 (18)
O2	0.161 (4)	0.177 (4)	0.075 (3)	0.115 (3)	0.076 (3)	0.085 (3)
O3	0.118 (3)	0.119 (3)	0.127 (3)	0.084 (3)	0.050 (3)	0.033 (3)
O4	0.137 (4)	0.122 (3)	0.136 (4)	0.083 (3)	0.037 (3)	0.013 (3)
O5	0.0501 (19)	0.0528 (18)	0.097 (2)	0.0245 (16)	0.0248 (17)	0.0461 (18)
N1	0.065 (2)	0.042 (2)	0.092 (3)	0.0293 (19)	0.037 (2)	0.035 (2)
N2	0.064 (3)	0.073 (3)	0.099 (3)	0.039 (2)	0.039 (2)	0.050 (3)
C1	0.169 (7)	0.195 (7)	0.096 (5)	0.143 (6)	0.064 (5)	0.062 (5)
C2	0.239 (9)	0.150 (6)	0.093 (5)	0.133 (6)	0.082 (6)	0.067 (5)
C3	0.100 (4)	0.053 (3)	0.064 (3)	0.036 (3)	0.039 (3)	0.028 (3)
C4	0.127 (4)	0.126 (4)	0.125 (4)	0.092 (3)	0.056 (3)	0.047 (3)
C5	0.127 (4)	0.126 (4)	0.125 (4)	0.092 (3)	0.056 (3)	0.047 (3)
C6	0.084 (3)	0.078 (3)	0.058 (3)	0.046 (3)	0.034 (3)	0.032 (2)
C7	0.059 (3)	0.044 (2)	0.060 (3)	0.029 (2)	0.027 (3)	0.027 (2)
C8	0.051 (3)	0.038 (2)	0.057 (3)	0.027 (2)	0.020 (3)	0.025 (2)
C9	0.090 (4)	0.045 (3)	0.053 (3)	0.037 (3)	0.030 (3)	0.024 (2)
C10	0.085 (4)	0.061 (3)	0.104 (5)	0.044 (3)	0.063 (4)	0.053 (3)
C11	0.048 (3)	0.063 (3)	0.120 (5)	0.021 (3)	0.032 (4)	0.044 (4)
C12	0.068 (4)	0.054 (3)	0.065 (3)	0.023 (3)	0.019 (3)	0.014 (3)
C13	0.062 (3)	0.048 (3)	0.062 (3)	0.032 (2)	0.031 (2)	0.025 (2)
C14	0.068 (3)	0.053 (3)	0.113 (4)	0.039 (3)	0.041 (3)	0.044 (3)
C15	0.062 (3)	0.059 (3)	0.060 (3)	0.025 (3)	0.036 (3)	0.027 (2)
C16	0.053 (3)	0.048 (3)	0.068 (3)	0.021 (2)	0.027 (3)	0.026 (2)

Geometric parameters (Å, º) top

Cl—C15	1.720 (5)	C3—H3A	0.9800
O1—C1	1.410 (6)	C4—H4A	0.9600
O1—C3	1.383 (5)	C4—H4B	0.9600
O2—C2	1.318 (6)	C4—H4C	0.9600
O2—C3	1.373 (5)	C5—C6	1.498 (8)
O3—C4	1.453 (6)	C6—C7	1.528 (6)
O3—C5	1.250 (7)	C6—H6A	0.9800
O4—C5	1.186 (8)	C7—C8	1.363 (5)
O5—C8	1.393 (4)	C7—C12	1.376 (6)
O5—C13	1.341 (5)	C8—C9	1.370 (6)
N1—C13	1.343 (5)	C9—C10	1.378 (6)
N1—C14	1.327 (5)	C9—H9A	0.9300
N2—C14	1.316 (5)	C10—C11	1.361 (7)
N2—C15	1.343 (5)	C10—H10A	0.9300
C1—H1B	0.9600	C11—C12	1.390 (7)
C1—H1C	0.9600	C11—H11A	0.9300
C1—H1D	0.9600	C12—H12A	0.9300
C2—H2B	0.9600	C13—C16	1.359 (5)
C2—H2C	0.9600	C14—H14A	0.9300
C2—H2D	0.9600	C15—C16	1.370 (5)
C3—C6	1.452 (6)	C16—H16A	0.9300

C3—O1—C1	117.8 (4)	C5—C6—C7	108.8 (4)
C2—O2—C3	126.5 (5)	C3—C6—H6A	106.1
C5—O3—C4	117.8 (5)	C5—C6—H6A	106.1
C13—O5—C8	121.1 (3)	C7—C6—H6A	106.1
C14—N1—C13	114.1 (4)	C8—C7—C12	116.5 (4)
C14—N2—C15	114.3 (4)	C8—C7—C6	119.9 (4)
O1—C1—H1B	109.5	C12—C7—C6	123.6 (4)
O1—C1—H1C	109.5	C7—C8—C9	123.0 (4)
H1B—C1—H1C	109.5	C7—C8—O5	117.6 (4)
O1—C1—H1D	109.5	C9—C8—O5	118.9 (4)
H1B—C1—H1D	109.5	C8—C9—C10	118.9 (4)
H1C—C1—H1D	109.5	C8—C9—H9A	120.5
O2—C2—H2B	109.5	C10—C9—H9A	120.5
O2—C2—H2C	109.5	C11—C10—C9	120.4 (5)
H2B—C2—H2C	109.5	C11—C10—H10A	119.8
O2—C2—H2D	109.5	C9—C10—H10A	119.8
H2B—C2—H2D	109.5	C10—C11—C12	118.7 (5)
H2C—C2—H2D	109.5	C10—C11—H11A	120.6
O2—C3—O1	114.2 (4)	C12—C11—H11A	120.6
O2—C3—C6	109.9 (4)	C7—C12—C11	122.4 (5)
O1—C3—C6	111.5 (4)	C7—C12—H12A	118.8
O2—C3—H3A	107.0	C11—C12—H12A	118.8
O1—C3—H3A	107.0	O5—C13—N1	119.0 (4)
C6—C3—H3A	107.0	O5—C13—C16	117.2 (4)
O3—C4—H4A	109.5	N1—C13—C16	123.9 (4)
O3—C4—H4B	109.5	N2—C14—N1	128.5 (4)
H4A—C4—H4B	109.5	N2—C14—H14A	115.7
O3—C4—H4C	109.5	N1—C14—H14A	115.7
H4A—C4—H4C	109.5	N2—C15—C16	123.5 (4)
H4B—C4—H4C	109.5	N2—C15—Cl	116.9 (4)
O4—C5—O3	123.8 (7)	C16—C15—Cl	119.6 (4)
O4—C5—C6	124.5 (7)	C13—C16—C15	115.6 (4)
O3—C5—C6	111.6 (7)	C13—C16—H16A	122.2
C3—C6—C5	112.0 (5)	C15—C16—H16A	122.2
C3—C6—C7	117.1 (4)

C2—O2—C3—O1	−67.6 (7)	C13—O5—C8—C7	−114.9 (4)
C2—O2—C3—C6	166.3 (6)	C13—O5—C8—C9	72.8 (5)
C1—O1—C3—O2	87.6 (6)	C7—C8—C9—C10	1.4 (6)
C1—O1—C3—C6	−147.2 (5)	O5—C8—C9—C10	173.3 (3)
C4—O3—C5—O4	−3.6 (11)	C8—C9—C10—C11	−1.0 (6)
C4—O3—C5—C6	173.0 (5)	C9—C10—C11—C12	0.4 (7)
O2—C3—C6—C5	−53.2 (6)	C8—C7—C12—C11	0.5 (6)
O1—C3—C6—C5	179.1 (5)	C6—C7—C12—C11	178.8 (4)
O2—C3—C6—C7	−179.9 (4)	C10—C11—C12—C7	−0.1 (7)
O1—C3—C6—C7	52.5 (6)	C8—O5—C13—N1	12.4 (6)
O4—C5—C6—C3	−54.2 (10)	C8—O5—C13—C16	−169.3 (4)
O3—C5—C6—C3	129.3 (6)	C14—N1—C13—O5	178.4 (4)
O4—C5—C6—C7	76.8 (8)	C14—N1—C13—C16	0.2 (6)
O3—C5—C6—C7	−99.7 (6)	C15—N2—C14—N1	0.9 (8)
C3—C6—C7—C8	−128.5 (4)	C13—N1—C14—N2	0.0 (8)
C5—C6—C7—C8	103.3 (5)	C14—N2—C15—C16	−2.0 (7)
C3—C6—C7—C12	53.2 (6)	C14—N2—C15—Cl	177.9 (4)
C5—C6—C7—C12	−75.0 (6)	O5—C13—C16—C15	−179.4 (4)
C12—C7—C8—C9	−1.1 (6)	N1—C13—C16—C15	−1.2 (7)
C6—C7—C8—C9	−179.5 (4)	N2—C15—C16—C13	2.2 (7)
C12—C7—C8—O5	−173.1 (3)	Cl—C15—C16—C13	−177.7 (3)
C6—C7—C8—O5	8.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O5	0.98	2.25	2.777 (6)	113
C1—H1B···Cg2ⁱ	0.96	2.97	3.696 (5)	134
C16—H16A···Cg1ⁱ	0.93	2.85	3.661 (4)	146

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇ClN₂O₅
M_r	352.77
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	9.5030 (19), 10.051 (2), 11.162 (2)
α, β, γ (°)	101.24 (3), 108.47 (3), 113.42 (3)
V (Å³)	862.6 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.20 × 0.20 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.952, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	3346, 3140, 1427
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.173, 1.07
No. of reflections	3140
No. of parameters	211
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.45

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O5	0.98	2.25	2.777 (6)	113
C1—H1B···Cg2ⁱ	0.96	2.97	3.696 (5)	134
C16—H16A···Cg1ⁱ	0.93	2.85	3.661 (4)	146

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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