N-Benzyl-2-hydroxy­benzamide

Zhang, Q.-X.; Zhang, B.-S.

doi:10.1107/S1600536808010453

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o884

doi:10.1107/S1600536808010453

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N-Benzyl-2-hydroxybenzamide

Qiu-Xia Zhang ^a ^* and Bi-Song Zhang ^a

^aCollege of Materials Science and Chemical Engineering, Jinhua College of Profession and Technology, Jinhua, Zhejiang 321017, People's Republic of China
^*Correspondence e-mail: zbs_jy@163.com

(Received 17 March 2008; accepted 16 April 2008; online 23 April 2008)

In the title compound, C₁₄H₁₃NO₂, the mean planes through the benzyl and 2-hydoxybenzamide units make a dihedral angle of 68.81 (7)°. There is an intramolecular O—H⋯O hydrogen bond involving the carbonyl O atom and the 2-hydroxy substituent. In the crystal structure, N—H⋯O hydrogen bonds link symmetry-related molecules into one-dimensional chains extending along the a-axis direction. These chains are further connected via C—H⋯O hydrogen bonds, forming a sheet-like structure

Related literature

For related literature, see: Agwade (1982 ); Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Monoclinic, P 2₁ /n
a = 12.478 (3) Å
b = 8.3503 (17) Å
c = 12.664 (3) Å
β = 118.02 (3)°
V = 1164.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 290 (2) K
0.33 × 0.22 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.977, T_max = 0.983
11112 measured reflections
2665 independent reflections
1648 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.116
S = 1.03
2665 reflections
207 parameters
All H-atom parameters refined
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1ⁱ	0.882 (18)	2.083 (18)	2.9191 (18)	158.1 (18)
O1—HO1⋯O2	0.98 (3)	1.56 (3)	2.4886 (19)	157 (2)
C2—H2⋯O1ⁱ	0.956 (19)	2.58 (2)	3.507 (2)	162.5 (15)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010453/su2048sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010453/su2048Isup2.hkl

checkCIF report

Comment top

Over a quater of a century ago (Agwade, 1982) published a thesis on Potential Central Nervous System Active Agents, which included the synthesis of aromatic N-benzyl amides. One of the compounds synthesized was N-benzyl-2-hydroxy-benzamide, (I), whose crystal structure has not been descibed until now.

The molecular structure of compound I is illustrated in Fig. 1. The bond lengths and angles are close to normal values (Allen et al., 1987). There is an intramolecular O-H···O hydrogen bond in the molecule involving the carbonyl O-atom and the 2-hydroxyl substituent (Table 1). The best planes through the benzyl (atoms C8,C9-C14) and the 2-hydoxybenzamide (atoms C1-C6,C7,N1,O1,O2) moieties are inclined to one another by 68.81 (7)°.

In the crystal structure of I symmetry related molecules are connected via an N-H···O hydrogen bond to form chains running along the a direction. These chains are further connected connected via C-H···O hydrogen bonds (Table 1) to form a sheet-like structure (Fig 2).

Related literature top

For related literature, see: Agwade (1982); Allen et al. (1987).

Experimental top

Freshly prepared CuCO₃ (0.310 g 2.50 mmol), [C₆H₄(COOC₆H₄CONHCH₂ph)₂](0.350 g 0.601 mmol), 2-chloro-benzoic acid (0.160 g 1.022 mmol), and 15 ml CH₃OH/H₂O (1:2,v/v) were mixed and stirred for ca. 1.5 h. The resulting suspension was heated in a 23 ml Teflon-lined stainless steel autoclave at 373 K for 7 days. After the autoclave was cooled to room temperature, and colorless block-like crystals, suitable for X-ray analysis, were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the moleculecular structure of I, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. The crystal packing diagram for compound I, viewed down the b axis. Dashed lines indicate N-H···O hydrogen bonds.

N-Benzyl-2-hydroxybenzamide top

Crystal data top

C₁₄H₁₃NO₂	F(000) = 480
M_r = 227.25	D_x = 1.296 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6913 reflections
a = 12.478 (3) Å	θ = 3.0–27.5°
b = 8.3503 (17) Å	µ = 0.09 mm⁻¹
c = 12.664 (3) Å	T = 290 K
β = 118.02 (3)°	Block, colorless
V = 1164.9 (6) Å³	0.33 × 0.22 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2665 independent reflections
Radiation source: fine-focus sealed tube	1648 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −15→16
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
T_min = 0.977, T_max = 0.983	l = −16→16
11112 measured reflections

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)] = 0.043	All H-atom parameters refined
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0564P)² + 0.0491P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2665 reflections	Δρ_max = 0.17 e Å⁻³
207 parameters	Δρ_min = −0.14 e Å⁻³
0 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 (2)

Crystal data top

C₁₄H₁₃NO₂	V = 1164.9 (6) Å³
M_r = 227.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.478 (3) Å	µ = 0.09 mm⁻¹
b = 8.3503 (17) Å	T = 290 K
c = 12.664 (3) Å	0.33 × 0.22 × 0.20 mm
β = 118.02 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2665 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1648 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.983	R_int = 0.037
11112 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.116	All H-atom parameters refined
S = 1.03	Δρ_max = 0.17 e Å⁻³
2665 reflections	Δρ_min = −0.14 e Å⁻³
207 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.29704 (10)	0.74227 (17)	−0.23736 (9)	0.0731 (4)
O2	0.49480 (9)	0.60089 (14)	−0.16419 (9)	0.0600 (4)
N1	0.64585 (9)	0.63326 (15)	0.02206 (11)	0.0449 (4)
C1	0.45255 (11)	0.76116 (16)	−0.03318 (11)	0.0396 (4)
C2	0.48553 (14)	0.82179 (19)	0.07995 (14)	0.0493 (5)
C3	0.40715 (15)	0.9140 (2)	0.10230 (16)	0.0592 (6)
C4	0.29300 (15)	0.9477 (2)	0.01061 (17)	0.0604 (6)
C5	0.25762 (14)	0.8909 (2)	−0.10172 (16)	0.0576 (6)
C6	0.33637 (12)	0.79771 (18)	−0.12499 (13)	0.0478 (5)
C7	0.53270 (11)	0.66022 (17)	−0.06264 (12)	0.0412 (4)
C8	0.73259 (14)	0.5375 (2)	0.00128 (16)	0.0508 (5)
C9	0.80422 (12)	0.63678 (17)	−0.04347 (14)	0.0460 (5)
C10	0.92320 (15)	0.6768 (3)	0.03099 (19)	0.0722 (7)
C11	0.98716 (18)	0.7699 (3)	−0.0108 (2)	0.0875 (9)
C12	0.9333 (2)	0.8228 (3)	−0.1254 (2)	0.0785 (9)
C13	0.81540 (19)	0.7850 (3)	−0.20000 (19)	0.0721 (8)
C14	0.75139 (16)	0.6917 (2)	−0.15893 (16)	0.0596 (6)
HN1	0.6728 (14)	0.6819 (19)	0.0917 (16)	0.059 (5)*
H2	0.5651 (15)	0.7995 (18)	0.1431 (15)	0.060 (5)*
HO1	0.367 (2)	0.681 (3)	−0.230 (2)	0.106 (7)*
H3	0.4331 (15)	0.952 (2)	0.1817 (17)	0.078 (5)*
H4	0.2386 (15)	1.009 (2)	0.0252 (15)	0.071 (5)*
H5	0.1770 (17)	0.913 (2)	−0.1697 (16)	0.081 (5)*
H8A	0.6833 (14)	0.455 (2)	−0.0610 (14)	0.062 (5)*
H8B	0.7896 (14)	0.4913 (19)	0.0805 (15)	0.062 (5)*
H10	0.9607 (17)	0.633 (2)	0.1088 (19)	0.087 (6)*
H11	1.070 (2)	0.793 (3)	0.042 (2)	0.107 (7)*
H12	0.9743 (19)	0.887 (3)	−0.1597 (18)	0.099 (7)*
H13	0.7716 (18)	0.825 (3)	−0.283 (2)	0.098 (7)*
H14	0.6696 (16)	0.668 (2)	−0.2122 (15)	0.070 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0512 (6)	0.1059 (10)	0.0395 (6)	0.0150 (7)	0.0024 (5)	−0.0056 (6)
O2	0.0503 (6)	0.0798 (8)	0.0421 (6)	0.0005 (5)	0.0152 (5)	−0.0147 (5)
N1	0.0376 (6)	0.0549 (8)	0.0399 (7)	0.0001 (5)	0.0162 (5)	0.0025 (6)
C1	0.0369 (6)	0.0420 (8)	0.0378 (7)	−0.0052 (6)	0.0159 (5)	0.0030 (6)
C2	0.0465 (8)	0.0557 (10)	0.0433 (8)	−0.0040 (7)	0.0190 (7)	−0.0014 (7)
C3	0.0664 (10)	0.0594 (10)	0.0604 (11)	−0.0070 (8)	0.0370 (9)	−0.0106 (8)
C4	0.0586 (10)	0.0493 (10)	0.0853 (13)	0.0013 (8)	0.0438 (9)	0.0000 (9)
C5	0.0440 (8)	0.0553 (10)	0.0696 (11)	0.0052 (7)	0.0235 (8)	0.0109 (8)
C6	0.0408 (7)	0.0533 (9)	0.0436 (8)	−0.0018 (7)	0.0150 (6)	0.0048 (7)
C7	0.0379 (7)	0.0458 (8)	0.0374 (8)	−0.0052 (6)	0.0156 (5)	0.0021 (6)
C8	0.0454 (8)	0.0501 (9)	0.0583 (10)	0.0065 (7)	0.0256 (7)	0.0099 (8)
C9	0.0447 (7)	0.0410 (8)	0.0558 (9)	0.0018 (6)	0.0266 (6)	−0.0020 (7)
C10	0.0477 (9)	0.0840 (14)	0.0753 (13)	−0.0025 (9)	0.0209 (8)	0.0173 (11)
C11	0.0510 (11)	0.0993 (17)	0.1074 (18)	−0.0151 (11)	0.0333 (11)	0.0117 (13)
C12	0.0808 (13)	0.0764 (14)	0.1031 (17)	−0.0141 (11)	0.0639 (13)	−0.0013 (12)
C13	0.0835 (13)	0.0814 (14)	0.0652 (12)	−0.0113 (10)	0.0464 (10)	0.0005 (10)
C14	0.0579 (10)	0.0695 (11)	0.0538 (10)	−0.0107 (8)	0.0283 (8)	−0.0039 (8)

Geometric parameters (Å, º) top

O1—C6	1.3506 (18)	C10—C11	1.385 (3)
O2—C7	1.2456 (17)	C11—C12	1.355 (3)
O1—HO1	0.98 (3)	C12—C13	1.360 (4)
N1—C7	1.3311 (19)	C13—C14	1.381 (3)
N1—C8	1.466 (2)	C2—H2	0.956 (19)
N1—HN1	0.882 (18)	C3—H3	0.954 (19)
C1—C7	1.483 (2)	C4—H4	0.94 (2)
C1—C6	1.401 (2)	C5—H5	0.99 (2)
C1—C2	1.387 (2)	C8—H8A	1.010 (16)
C2—C3	1.375 (3)	C8—H8B	0.995 (17)
C3—C4	1.379 (3)	C10—H10	0.94 (2)
C4—C5	1.361 (3)	C11—H11	0.95 (3)
C5—C6	1.389 (3)	C12—H12	0.97 (3)
C8—C9	1.511 (3)	C13—H13	0.99 (2)
C9—C14	1.370 (2)	C14—H14	0.94 (2)
C9—C10	1.375 (3)

O1···O2	2.4886 (19)	C9···H4^iv	3.034 (17)
O1···N1ⁱ	2.9191 (18)	C14···H4^iv	2.989 (17)
O2···C14	3.260 (3)	HN1···C2	2.554 (19)
O2···O1	2.4886 (19)	HN1···H2	2.00 (3)
O1···H2ⁱ	2.58 (2)	HN1···O1ⁱⁱⁱ	2.083 (18)
O1···HN1ⁱ	2.083 (18)	H2···N1	2.597 (18)
O2···HO1	1.56 (3)	H2···HN1	2.00 (3)
O2···H8A	2.416 (18)	H2···O1ⁱⁱⁱ	2.58 (2)
O2···H14	2.59 (2)	HO1···O2	1.56 (3)
O2···H5ⁱⁱ	2.692 (19)	HO1···C7	2.16 (2)
N1···O1ⁱⁱⁱ	2.9191 (18)	HO1···H5ⁱⁱ	2.50 (3)
N1···H2	2.597 (18)	H4···C9^iv	3.034 (17)
C1···C3^iv	3.554 (2)	H4···C14^iv	2.989 (17)
C1···C8^v	3.549 (2)	H5···O2^vi	2.692 (19)
C3···C1^iv	3.554 (2)	H5···HO1^vi	2.50 (3)
C6···C8^v	3.507 (2)	H8A···O2	2.416 (18)
C7···C7^v	3.400 (2)	H8A···H14	2.56 (2)
C7···C14	3.483 (3)	H8A···H13^vii	2.54 (3)
C8···C1^v	3.549 (2)	H8A···C1^v	3.075 (18)
C8···C6^v	3.507 (2)	H8A···C2^v	3.060 (18)
C14···C7	3.483 (3)	H8B···H10	2.32 (3)
C14···O2	3.260 (3)	H8B···C6^v	3.073 (17)
C1···H8A^v	3.075 (18)	H10···H8B	2.32 (3)
C2···H8A^v	3.060 (18)	H13···H8A^viii	2.54 (3)
C2···HN1	2.554 (19)	H14···O2	2.59 (2)
C6···H8B^v	3.073 (17)	H14···C7	3.09 (2)
C7···H14	3.09 (2)	H14···H8A	2.56 (2)
C7···HO1	2.16 (2)

C6—O1—HO1	102.3 (13)	C9—C14—C13	121.17 (19)
C7—N1—C8	122.74 (13)	C1—C2—H2	118.7 (11)
C7—N1—HN1	119.3 (12)	C3—C2—H2	119.8 (11)
C8—N1—HN1	117.7 (13)	C2—C3—H3	118.8 (12)
C6—C1—C7	118.17 (12)	C4—C3—H3	121.6 (12)
C2—C1—C6	117.83 (15)	C3—C4—H4	120.2 (11)
C2—C1—C7	124.00 (14)	C5—C4—H4	119.2 (11)
C1—C2—C3	121.50 (16)	C4—C5—H5	122.9 (12)
C2—C3—C4	119.62 (17)	C6—C5—H5	116.9 (12)
C3—C4—C5	120.55 (19)	N1—C8—H8A	106.4 (11)
C4—C5—C6	120.15 (17)	N1—C8—H8B	105.6 (11)
C1—C6—C5	120.35 (14)	C9—C8—H8A	109.4 (10)
O1—C6—C1	121.46 (15)	C9—C8—H8B	108.8 (11)
O1—C6—C5	118.19 (15)	H8A—C8—H8B	114.1 (13)
O2—C7—C1	120.79 (13)	C9—C10—H10	117.9 (14)
O2—C7—N1	120.61 (14)	C11—C10—H10	121.6 (14)
N1—C7—C1	118.60 (12)	C10—C11—H11	118.5 (15)
N1—C8—C9	112.64 (13)	C12—C11—H11	121.0 (15)
C8—C9—C10	120.97 (16)	C11—C12—H12	123.9 (13)
C8—C9—C14	120.74 (16)	C13—C12—H12	116.2 (13)
C10—C9—C14	118.28 (18)	C12—C13—H13	122.5 (15)
C9—C10—C11	120.3 (2)	C14—C13—H13	117.6 (15)
C10—C11—C12	120.5 (2)	C9—C14—H14	120.7 (11)
C11—C12—C13	119.9 (2)	C13—C14—H14	118.2 (11)
C12—C13—C14	119.8 (2)

C8—N1—C7—O2	1.6 (2)	C2—C3—C4—C5	−0.2 (3)
C8—N1—C7—C1	−178.95 (14)	C3—C4—C5—C6	0.2 (3)
C7—N1—C8—C9	89.06 (18)	C4—C5—C6—O1	179.22 (16)
C6—C1—C2—C3	0.4 (2)	C4—C5—C6—C1	0.1 (2)
C7—C1—C2—C3	−179.59 (16)	N1—C8—C9—C10	104.4 (2)
C2—C1—C6—O1	−179.48 (15)	N1—C8—C9—C14	−74.4 (2)
C2—C1—C6—C5	−0.4 (2)	C8—C9—C10—C11	−179.0 (2)
C7—C1—C6—O1	0.5 (2)	C14—C9—C10—C11	−0.2 (3)
C7—C1—C6—C5	179.56 (15)	C8—C9—C14—C13	178.77 (18)
C2—C1—C7—O2	175.27 (15)	C10—C9—C14—C13	−0.1 (3)
C2—C1—C7—N1	−4.2 (2)	C9—C10—C11—C12	0.1 (4)
C6—C1—C7—O2	−4.7 (2)	C10—C11—C12—C13	0.3 (4)
C6—C1—C7—N1	175.80 (14)	C11—C12—C13—C14	−0.6 (4)
C1—C2—C3—C4	−0.1 (3)	C12—C13—C14—C9	0.5 (3)

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+1/2, y−1/2, −z−1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) −x+1, −y+2, −z; (v) −x+1, −y+1, −z; (vi) −x+1/2, y+1/2, −z−1/2; (vii) −x+3/2, y−1/2, −z−1/2; (viii) −x+3/2, y+1/2, −z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1ⁱⁱⁱ	0.882 (18)	2.083 (18)	2.9191 (18)	158.1 (18)
O1—HO1···O2	0.98 (3)	1.56 (3)	2.4886 (19)	157 (2)
C2—H2···O1ⁱⁱⁱ	0.956 (19)	2.58 (2)	3.507 (2)	162.5 (15)
C14—H14···O2	0.94 (2)	2.59 (2)	3.260 (3)	128.8 (14)

Symmetry code: (iii) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	290
a, b, c (Å)	12.478 (3), 8.3503 (17), 12.664 (3)
β (°)	118.02 (3)
V (Å³)	1164.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.977, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	11112, 2665, 1648
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.116, 1.03
No. of reflections	2665
No. of parameters	207
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.14

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), 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—HN1···O1ⁱ	0.882 (18)	2.083 (18)	2.9191 (18)	158.1 (18)
O1—HO1···O2	0.98 (3)	1.56 (3)	2.4886 (19)	157 (2)
C2—H2···O1ⁱ	0.956 (19)	2.58 (2)	3.507 (2)	162.5 (15)

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

Acknowledgements

The authors gratefully acknowledge the financial support of the Education Office of Zhejiang Province (grant No. 20051316).

References

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