2,5-Bis[(3-hy­droxy­prop­yl)amino]-1,4-benzoquinone monohydrate

Wang, J.; Liu, W.; Guan, T.; Yin, F.; Sun, Y.

doi:10.1107/S1600536811021635

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1632

doi:10.1107/S1600536811021635

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2,5-Bis[(3-hydroxypropyl)amino]-1,4-benzoquinone monohydrate

Jian Wang,^a ^* Weiwei Liu,^a Tongwei Guan,^a Fujun Yin ^a and Yuxi Sun ^b

^aSchool of Chemical Engineering, Huaihai Institute of Technology, Lianyungang Jiangsu, People's Republic of China, and ^bQufu Normal University, Qufu Shandong, People's Republic of China
^*Correspondence e-mail: wjsxhwhp@yahoo.cn

(Received 29 April 2011; accepted 5 June 2011; online 11 June 2011)

The title compound, C₁₂H₁₈N₂O₄·H₂O, was obtained as a product of the reaction of hydroquinone with n-propanol amine. The compound crystallizes as a monohydrate, integrating water into its hydrogen-bonded network. Each diaminoquinone moiety forms two centrosymmetric 10-membered rings through C=O⋯H—N bonds. The resulting bands along [102] are interlinked through hydroxy groups and water molecules into three-dimensional network. The chemically equivalent bond lengths in the diaminoquinone moiety exhibit a perceptible discrepancy [e.g. C=O bond lengths differ by 0.016 (2) Å], apparently as a result of asymmetric hydrogen bonding: one O atom serves as an acceptor of one hydrogen bond, whereas the other is an acceptor of two.

Related literature

For the synthesis of the title compound see: Jian et al. (2009 ). For related literature on aminoquinones, see: Der (2010 ), Nisha et al. (2010 ).

Experimental

Crystal data

C₁₂H₁₈N₂O₄·H₂O
M_r = 272.30
Triclinic, $[P \overline 1]$
a = 4.9272 (8) Å
b = 11.673 (2) Å
c = 11.933 (2) Å
α = 82.104 (2)°
β = 87.994 (2)°
γ = 80.849 (2)°
V = 671.13 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.25 × 0.18 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.974, T_max = 0.989
5966 measured reflections
2895 independent reflections
1963 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.116
S = 1.03
2895 reflections
196 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O4ⁱ	0.85 (1)	1.98 (1)	2.818 (2)	168 (2)
O5—H5A⋯O3ⁱⁱ	0.85 (1)	1.90 (1)	2.736 (2)	169 (2)
O3—H3⋯O2ⁱⁱ	0.84 (2)	1.90 (2)	2.7398 (19)	173 (3)
N1—H1⋯O2ⁱⁱ	0.89 (1)	2.20 (1)	2.9865 (18)	146 (2)
N2—H2⋯O1ⁱⁱⁱ	0.89 (1)	2.17 (1)	2.9508 (17)	146 (2)
O4—H4⋯O5^iv	0.85 (2)	1.88 (2)	2.727 (2)	173 (2)
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y, -z+1; (iii) -x+3, -y, -z; (iv) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536811021635/ld2011sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021635/ld2011Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021635/ld2011Isup3.cml

checkCIF report

Comment top

Aminoquinones are used as medicines and herbicides and have interesting redox switching properties. They are formed in the reactions of different amines with quinones or hydroquinone. For example, 1,4-benzoquinone reacts with primary amines to give 2,5-diamino-1,4-benzoquinones. Recently, by reacting hydroquinone with n-propanol amine, 2,5-di[(3-hydroxypropyl)amino]-1,4-benzoquinone has been synthesized. The product was characterized with IR, UV and mass spectrometry, as well as NMR. This and related compounds are of considerable interest since they exhibit potent antitumor and antimalarial activities. However, the single-crystal structure of 2,5-di[(3-hydroxypropyl)amino]-1,4-benzoquinone has not been reported.

Related literature top

For the synthesis of the title compound see: Jian et al. (2009). For related literature [on what subject?], see: Der (2010), Nisha et al. (2010).

Experimental top

Methanol solution (10 ml) of n-propanol amine(2.3 mmol) was added to methanol solution (10 ml) of hydroquinone (0.05 g=0.46 mmol), and was stirred for 0.5 h at room temperature. Then the reaction was refluxed at 50°C for 4 h. A deep-red ropiness crude product was formed. The product was purified by recrystallization from methanol. Long red flat prisms were obtained from methanol solution after vaporizing at room temperature for two weeks.

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); 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 structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound.

2,5-Bis[(3-hydroxypropyl)amino]-1,4-benzoquinone monohydrate top

Crystal data top

C₁₂H₁₈N₂O₄·H₂O	Z = 2
M_r = 272.30	F(000) = 292
Triclinic, P1	D_x = 1.347 Mg m⁻³
Hall symbol: -P 1	Melting point = 437.1–438.3 K
a = 4.9272 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.673 (2) Å	Cell parameters from 1436 reflections
c = 11.933 (2) Å	θ = 2.6–26.1°
α = 82.104 (2)°	µ = 0.11 mm⁻¹
β = 87.994 (2)°	T = 296 K
γ = 80.849 (2)°	Strip, red
V = 671.13 (19) Å³	0.25 × 0.18 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	2895 independent reflections
Radiation source: fine-focus sealed tube	1963 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −6→6
T_min = 0.974, T_max = 0.989	k = −14→14
5966 measured reflections	l = −14→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0454P)² + 0.0971P] where P = (F_o² + 2F_c²)/3
2895 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.20 e Å⁻³
7 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₂H₁₈N₂O₄·H₂O	γ = 80.849 (2)°
M_r = 272.30	V = 671.13 (19) Å³
Triclinic, P1	Z = 2
a = 4.9272 (8) Å	Mo Kα radiation
b = 11.673 (2) Å	µ = 0.11 mm⁻¹
c = 11.933 (2) Å	T = 296 K
α = 82.104 (2)°	0.25 × 0.18 × 0.11 mm
β = 87.994 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2895 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	1963 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.989	R_int = 0.025
5966 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	7 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
2895 reflections	Δρ_min = −0.20 e Å⁻³
196 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
N1	0.6153 (3)	−0.11927 (12)	0.36773 (12)	0.0390 (4)
N2	1.3092 (3)	0.13162 (11)	0.10709 (11)	0.0351 (3)
O1	1.2722 (3)	−0.08231 (10)	0.07011 (10)	0.0453 (3)
O2	0.6703 (3)	0.09049 (10)	0.41065 (10)	0.0552 (4)
O3	0.5303 (4)	−0.32465 (13)	0.60246 (12)	0.0736 (5)
O4	1.0113 (3)	0.41209 (12)	−0.14943 (12)	0.0565 (4)
O5	0.5089 (3)	0.49169 (15)	0.21551 (15)	0.0768 (5)
C1	1.1245 (3)	−0.04600 (13)	0.14826 (13)	0.0314 (4)
C2	0.9446 (3)	−0.11051 (13)	0.21472 (13)	0.0340 (4)
H2A	0.9286	−0.1851	0.1994	0.041*
C3	0.7922 (3)	−0.06574 (13)	0.30165 (13)	0.0317 (4)
C4	0.8147 (3)	0.05513 (13)	0.32951 (13)	0.0351 (4)
C5	0.9895 (3)	0.12030 (13)	0.26347 (13)	0.0349 (4)
H5	1.0042	0.1949	0.2793	0.042*
C6	1.1415 (3)	0.07683 (12)	0.17496 (13)	0.0293 (3)
C7	0.5507 (4)	−0.23474 (14)	0.35927 (14)	0.0396 (4)
H7A	0.5450	−0.2441	0.2799	0.048*
H7B	0.3688	−0.2399	0.3915	0.048*
C8	0.7530 (4)	−0.33485 (14)	0.41825 (14)	0.0435 (4)
H8A	0.6915	−0.4084	0.4109	0.052*
H8B	0.9311	−0.3353	0.3809	0.052*
C9	0.7835 (5)	−0.32661 (18)	0.54126 (16)	0.0589 (6)
H9A	0.9135	−0.3930	0.5742	0.071*
H9B	0.8582	−0.2560	0.5486	0.071*
C10	1.3668 (4)	0.24973 (13)	0.10990 (14)	0.0380 (4)
H10A	1.5559	0.2458	0.1321	0.046*
H10B	1.2486	0.2859	0.1662	0.046*
C11	1.3213 (3)	0.32460 (13)	−0.00383 (13)	0.0339 (4)
H11A	1.3914	0.3974	−0.0017	0.041*
H11B	1.4254	0.2842	−0.0612	0.041*
C12	1.0238 (3)	0.35224 (14)	−0.03697 (14)	0.0382 (4)
H12A	0.9458	0.2806	−0.0334	0.046*
H12B	0.9203	0.4011	0.0142	0.046*
H5A	0.516 (5)	0.4429 (17)	0.2754 (14)	0.092 (8)*
H5B	0.662 (3)	0.516 (2)	0.205 (2)	0.099 (9)*
H2	1.405 (4)	0.0890 (14)	0.0584 (13)	0.059 (6)*
H1	0.535 (4)	−0.0797 (15)	0.4219 (13)	0.063 (6)*
H4	0.844 (4)	0.437 (2)	−0.167 (2)	0.087 (8)*
H3	0.456 (5)	−0.2541 (16)	0.601 (2)	0.097 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0467 (9)	0.0316 (7)	0.0382 (8)	−0.0087 (6)	0.0157 (7)	−0.0043 (6)
N2	0.0405 (8)	0.0283 (7)	0.0361 (8)	−0.0068 (6)	0.0112 (6)	−0.0038 (6)
O1	0.0546 (8)	0.0366 (6)	0.0459 (7)	−0.0097 (5)	0.0247 (6)	−0.0129 (5)
O2	0.0752 (9)	0.0391 (7)	0.0519 (8)	−0.0121 (6)	0.0359 (7)	−0.0138 (6)
O3	0.1126 (14)	0.0458 (9)	0.0477 (8)	0.0110 (8)	0.0317 (9)	0.0102 (7)
O4	0.0473 (9)	0.0658 (9)	0.0505 (8)	−0.0093 (7)	−0.0054 (7)	0.0146 (7)
O5	0.0648 (11)	0.0847 (12)	0.0740 (11)	−0.0315 (9)	−0.0232 (9)	0.0418 (9)
C1	0.0345 (9)	0.0279 (8)	0.0299 (8)	−0.0004 (6)	0.0051 (7)	−0.0045 (6)
C2	0.0404 (9)	0.0262 (8)	0.0353 (9)	−0.0063 (7)	0.0074 (7)	−0.0048 (7)
C3	0.0336 (9)	0.0291 (8)	0.0303 (8)	−0.0034 (6)	0.0051 (7)	0.0008 (6)
C4	0.0404 (9)	0.0306 (8)	0.0319 (8)	−0.0007 (7)	0.0103 (7)	−0.0039 (7)
C5	0.0425 (10)	0.0266 (8)	0.0357 (9)	−0.0067 (7)	0.0098 (7)	−0.0057 (7)
C6	0.0295 (8)	0.0271 (8)	0.0290 (8)	−0.0021 (6)	0.0018 (6)	0.0013 (6)
C7	0.0440 (10)	0.0397 (9)	0.0362 (9)	−0.0149 (7)	0.0051 (8)	−0.0001 (7)
C8	0.0511 (11)	0.0349 (9)	0.0438 (10)	−0.0062 (8)	0.0093 (9)	−0.0057 (8)
C9	0.0730 (15)	0.0495 (12)	0.0475 (12)	0.0083 (10)	−0.0057 (11)	−0.0018 (9)
C10	0.0418 (10)	0.0338 (9)	0.0391 (9)	−0.0123 (7)	0.0037 (8)	−0.0014 (7)
C11	0.0351 (9)	0.0292 (8)	0.0371 (9)	−0.0079 (7)	0.0068 (7)	−0.0026 (7)
C12	0.0388 (10)	0.0341 (9)	0.0415 (10)	−0.0073 (7)	0.0050 (8)	−0.0043 (7)

Geometric parameters (Å, º) top

N1—C3	1.3273 (19)	C4—C5	1.392 (2)
N1—C7	1.451 (2)	C5—C6	1.380 (2)
N1—H1	0.891 (9)	C5—H5	0.9300
N2—C6	1.3140 (19)	C7—C8	1.519 (2)
N2—C10	1.456 (2)	C7—H7A	0.9700
N2—H2	0.891 (9)	C7—H7B	0.9700
O1—C1	1.2419 (17)	C8—C9	1.499 (3)
O2—C4	1.2580 (18)	C8—H8A	0.9700
O3—C9	1.422 (2)	C8—H8B	0.9700
O3—H3	0.844 (16)	C9—H9A	0.9700
O4—C12	1.424 (2)	C9—H9B	0.9700
O4—H4	0.850 (16)	C10—C11	1.513 (2)
O5—H5A	0.849 (9)	C10—H10A	0.9700
O5—H5B	0.849 (9)	C10—H10B	0.9700
C1—C2	1.407 (2)	C11—C12	1.504 (2)
C1—C6	1.526 (2)	C11—H11A	0.9700
C2—C3	1.372 (2)	C11—H11B	0.9700
C2—H2A	0.9300	C12—H12A	0.9700
C3—C4	1.515 (2)	C12—H12B	0.9700

C3—N1—C7	125.40 (14)	H7A—C7—H7B	107.6
C3—N1—H1	115.3 (13)	C9—C8—C7	112.93 (15)
C7—N1—H1	119.3 (13)	C9—C8—H8A	109.0
C6—N2—C10	126.63 (14)	C7—C8—H8A	109.0
C6—N2—H2	115.3 (12)	C9—C8—H8B	109.0
C10—N2—H2	117.9 (12)	C7—C8—H8B	109.0
C9—O3—H3	108.2 (18)	H8A—C8—H8B	107.8
C12—O4—H4	109.4 (17)	O3—C9—C8	112.68 (18)
H5A—O5—H5B	109.4 (18)	O3—C9—H9A	109.1
O1—C1—C2	124.65 (14)	C8—C9—H9A	109.1
O1—C1—C6	117.67 (13)	O3—C9—H9B	109.1
C2—C1—C6	117.68 (13)	C8—C9—H9B	109.1
C3—C2—C1	121.45 (14)	H9A—C9—H9B	107.8
C3—C2—H2A	119.3	N2—C10—C11	111.84 (13)
C1—C2—H2A	119.3	N2—C10—H10A	109.2
N1—C3—C2	125.71 (15)	C11—C10—H10A	109.2
N1—C3—C4	113.62 (13)	N2—C10—H10B	109.2
C2—C3—C4	120.67 (13)	C11—C10—H10B	109.2
O2—C4—C5	124.28 (15)	H10A—C10—H10B	107.9
O2—C4—C3	117.34 (14)	C12—C11—C10	113.21 (13)
C5—C4—C3	118.38 (13)	C12—C11—H11A	108.9
C6—C5—C4	121.53 (14)	C10—C11—H11A	108.9
C6—C5—H5	119.2	C12—C11—H11B	108.9
C4—C5—H5	119.2	C10—C11—H11B	108.9
N2—C6—C5	126.20 (14)	H11A—C11—H11B	107.7
N2—C6—C1	113.53 (13)	O4—C12—C11	107.74 (13)
C5—C6—C1	120.27 (13)	O4—C12—H12A	110.2
N1—C7—C8	114.31 (14)	C11—C12—H12A	110.2
N1—C7—H7A	108.7	O4—C12—H12B	110.2
C8—C7—H7A	108.7	C11—C12—H12B	110.2
N1—C7—H7B	108.7	H12A—C12—H12B	108.5
C8—C7—H7B	108.7

O1—C1—C2—C3	178.39 (16)	C10—N2—C6—C1	179.18 (14)
C6—C1—C2—C3	−0.9 (2)	C4—C5—C6—N2	179.17 (16)
C7—N1—C3—C2	−0.3 (3)	C4—C5—C6—C1	−0.9 (2)
C7—N1—C3—C4	179.25 (15)	O1—C1—C6—N2	2.2 (2)
C1—C2—C3—N1	179.10 (16)	C2—C1—C6—N2	−178.43 (15)
C1—C2—C3—C4	−0.4 (2)	O1—C1—C6—C5	−177.71 (15)
N1—C3—C4—O2	0.8 (2)	C2—C1—C6—C5	1.7 (2)
C2—C3—C4—O2	−179.63 (16)	C3—N1—C7—C8	83.0 (2)
N1—C3—C4—C5	−178.40 (15)	N1—C7—C8—C9	56.7 (2)
C2—C3—C4—C5	1.2 (2)	C7—C8—C9—O3	58.3 (2)
O2—C4—C5—C6	−179.57 (16)	C6—N2—C10—C11	−126.19 (17)
C3—C4—C5—C6	−0.5 (2)	N2—C10—C11—C12	68.29 (17)
C10—N2—C6—C5	−0.9 (3)	C10—C11—C12—O4	−174.07 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O4ⁱ	0.85 (1)	1.98 (1)	2.818 (2)	168 (2)
O5—H5A···O3ⁱⁱ	0.85 (1)	1.90 (1)	2.736 (2)	169 (2)
O3—H3···O2ⁱⁱ	0.84 (2)	1.90 (2)	2.7398 (19)	173 (3)
N1—H1···O2ⁱⁱ	0.89 (1)	2.20 (1)	2.9865 (18)	146 (2)
N2—H2···O1ⁱⁱⁱ	0.89 (1)	2.17 (1)	2.9508 (17)	146 (2)
O4—H4···O5^iv	0.85 (2)	1.88 (2)	2.727 (2)	173 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₈N₂O₄·H₂O
M_r	272.30
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	4.9272 (8), 11.673 (2), 11.933 (2)
α, β, γ (°)	82.104 (2), 87.994 (2), 80.849 (2)
V (Å³)	671.13 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.18 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.974, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	5966, 2895, 1963
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.116, 1.03
No. of reflections	2895
No. of parameters	196
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), 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
O5—H5B···O4ⁱ	0.849 (9)	1.982 (10)	2.818 (2)	168 (2)
O5—H5A···O3ⁱⁱ	0.849 (9)	1.899 (10)	2.736 (2)	169 (2)
O3—H3···O2ⁱⁱ	0.844 (16)	1.900 (17)	2.7398 (19)	173 (3)
N1—H1···O2ⁱⁱ	0.891 (9)	2.204 (14)	2.9865 (18)	146.2 (17)
N2—H2···O1ⁱⁱⁱ	0.891 (9)	2.170 (13)	2.9508 (17)	146.0 (17)
O4—H4···O5^iv	0.850 (16)	1.881 (17)	2.727 (2)	173 (2)

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

Acknowledgements

We acknowledge the financial support of the foundation of Jiangsu Key Laboratory of Marine Biotechnology (2010HS07), the Jiangsu Marine Resources Development Research Institute (JSIMR10E02), the Major Program of the Natural Science Foundation of Jiangsu Education Committee (10 K J A170003), the Natural Science Foundation of Jiangsu Education Committee (08KJB150002), the Six Kinds of Professional Elite Foundation of Jiangsu Province (No. 07-A-024), the Science and Technology Critical Project Foundation of Lianyungang (CG0803–2), the Doctoral Scientific Research Project (KQ09006) and the partnership of Huaihai Institute of Technology.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS, Madison, Wisconsin, USA. Google Scholar
Der, P. C. (2010). Scholars Research Library. 2, 63–73 Google Scholar
Jian, W., Wei-wei, L., Wei-xing, M., Tong-wei, G., Xing-you, X., Lu-de, L. & Xu-ji, Y. (2009). J. Huaihai Institute of Technology (Natural Science Edition). 18, 34–37 Google Scholar
Nisha, M., Twinkle, K., Lakshmy, S. & Kalyanasundaram, M. (2010). Drug Dev. Res. 71, 188–196. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1632

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