N-{2-[4-(2-Hy­droxy­eth­yl)piperazin-1-yl]eth­yl}phthalimide

Shao, Y.; An, D.; Zhou, M.; Liu, L.; Sun, X.-Q.

doi:10.1107/S160053681105327X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o173

doi:10.1107/S160053681105327X

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N-{2-[4-(2-Hydroxyethyl)piperazin-1-yl]ethyl}phthalimide

Ying Shao,^a ^* Dong An,^a Mi Zhou,^a Li Liu ^b and Xiao-Qiang Sun ^a

^aKey Laboratory of Fine Petrohemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China, and ^bAnalytical Center, Changzhou University, Changzhou 213164, People's Republic of China
^*Correspondence e-mail: yingshao@cczu.edu.cn

(Received 10 December 2011; accepted 10 December 2011; online 21 December 2011)

In the title compound, C₁₆H₂₁N₃O₃, the piperazine ring adopts a chair conformation, with its N—C bonds in pseudo-equatorial orientations. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, generating C(5) chains propagating in [101]. Weak aromatic π–π stacking interactions also occur [centroid–centroid separation = 3.899 (1) Å].

Related literature

For general background to piperazine derivatives, see: Tian et al. (2011 ). For the preparation, see: Ghosh et al. (2010 ).

Experimental

Crystal data

C₁₆H₂₁N₃O₃
M_r = 303.36
Monoclinic, P 2₁ /n
a = 5.8109 (6) Å
b = 37.012 (4) Å
c = 7.3537 (8) Å
β = 95.634 (2)°
V = 1573.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.25 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.978, T_max = 0.982
8562 measured reflections
2775 independent reflections
2537 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.161
S = 1.00
2775 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N3ⁱ	0.82	2.00	2.811 (3)	171
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 I, global. DOI: 10.1107/S160053681105327X/hb6564sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105327X/hb6564Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681105327X/hb6564Isup3.cdx

Supporting information file. DOI: 10.1107/S160053681105327X/hb6564Isup4.cml

checkCIF report

Comment top

Piperazine derivatives in pharmaceutical and chemical industries have a wide range of applications (Tian, et al., 2011). The title compound, which is an intermediate for our designed drug, was synthesized from 2-(2-bromoethyl)phthalimide and 2-(piperazin-1-yl)ethanol in the presence of K₂CO₃ as acid-acceptor (Ghosh, et al., 2010). In the molecule of the title compound (Fig. 1), the phthalimide fragment is planar, with r.m.s. deviation of 0.02 Å. The six-membered piperazine ring adopts the chair conformation. In the crystal, the crystal packing is stabilized by O—H···N hydrogen bonding interactions and π–π interactions involving the benzene ring (Fig. 2). For the O—H···N the hydrogen bonding interactions, the relevant distances and angles are: O3···H3A= 0.821 Å, H3A···N3 =1.997 Å, O3···N3^[i]= 2.811 (3) Å, and O3—H3A···N3^[i]= 171.3°. And for the π ···π interactions, the relevant distances are: Cg···Cg^[ii] = 3.899 (1)Å [symmetry code: (i) x - 1/2, 1/2 - y, -1/2 + z; (ii) 2 - x, -y, 2 - z; Cg is the centroid of the C1–C2–C3–C4–C5–C6 ring].

Related literature top

For general background to piperazine derivatives, see: Tian et al. (2011). For the preparation, see: Ghosh et al. (2010).

Experimental top

A suspension of 2-(2-bromoethyl)phthalimide (0.63 g, 2.5 mmol), 2-(piperazin-1-yl)ethanol (0.36 g, 2.8 mmol) and K₂CO₃ (0.90 g, 6.5 mmol) in 15 ml acetonitrile was stirred at room temperature for 0.5 h, and then heated to reflux for 10 h. After cooling and filtration, the filter residue was washed with CH₃CN. And the filtrate and washing were combined prior to removing the solvent under vacuum. A white powder (0.55 g, 1.8 mmol) was obtained after recrystallization from ethyl acetate/ petroleum ether. Colourless blocks were obtained by slow evaporation of a CH₃OH solution.

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. View of the title compound, showing 50% probability ellipsoids.
	Fig. 2. Perspective view of the title compound along c direction. Labels of atoms have been omitted for clarity.

(I) top

Crystal data top

C₁₆H₂₁N₃O₃	F(000) = 648
M_r = 303.36	D_x = 1.280 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5733 reflections
a = 5.8109 (6) Å	θ = 2.8–29.9°
b = 37.012 (4) Å	µ = 0.09 mm⁻¹
c = 7.3537 (8) Å	T = 296 K
β = 95.634 (2)°	Block, colorless
V = 1573.9 (3) Å³	0.25 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2775 independent reflections
Radiation source: fine-focus sealed tube	2537 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→6
T_min = 0.978, T_max = 0.982	k = −44→43
8562 measured reflections	l = −8→6

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)] = 0.057	H-atom parameters constrained
wR(F²) = 0.161	w = 1/[σ²(F_o²) + (0.081P)² + 1.190P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2775 reflections	Δρ_max = 0.53 e Å⁻³
201 parameters	Δρ_min = −0.38 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: 0.024 (4)

Crystal data top

C₁₆H₂₁N₃O₃	V = 1573.9 (3) Å³
M_r = 303.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8109 (6) Å	µ = 0.09 mm⁻¹
b = 37.012 (4) Å	T = 296 K
c = 7.3537 (8) Å	0.25 × 0.22 × 0.20 mm
β = 95.634 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2775 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2537 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.982	R_int = 0.025
8562 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.00	Δρ_max = 0.53 e Å⁻³
2775 reflections	Δρ_min = −0.38 e Å⁻³
201 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
C1	0.8296 (4)	0.04878 (5)	0.9736 (3)	0.0374 (5)
C2	0.7865 (4)	0.02500 (6)	1.1105 (3)	0.0471 (6)
H2	0.6530	0.0110	1.1024	0.057*
C3	0.9495 (5)	0.02280 (7)	1.2607 (3)	0.0522 (6)
H3	0.9260	0.0067	1.3543	0.063*
C4	1.1458 (5)	0.04391 (7)	1.2744 (3)	0.0538 (6)
H4	1.2518	0.0419	1.3773	0.065*
C5	1.1882 (4)	0.06811 (7)	1.1375 (3)	0.0496 (6)
H5	1.3199	0.0825	1.1466	0.060*
C6	1.0265 (4)	0.06991 (6)	0.9870 (3)	0.0389 (5)
C7	1.0250 (4)	0.09147 (6)	0.8160 (3)	0.0429 (5)
C8	0.6974 (4)	0.05594 (6)	0.7936 (3)	0.0414 (5)
C9	0.7626 (5)	0.09520 (6)	0.5245 (3)	0.0473 (6)
H9A	0.6659	0.0776	0.4558	0.057*
H9B	0.9024	0.0982	0.4640	0.057*
C10	0.6356 (4)	0.13096 (6)	0.5228 (3)	0.0398 (5)
H10A	0.5043	0.1288	0.5940	0.048*
H10B	0.7380	0.1494	0.5789	0.048*
C11	0.7464 (4)	0.15193 (6)	0.2321 (3)	0.0412 (5)
H11A	0.8526	0.1318	0.2290	0.049*
H11B	0.8300	0.1721	0.2916	0.049*
C12	0.6585 (4)	0.16244 (6)	0.0396 (3)	0.0432 (5)
H12A	0.7881	0.1687	−0.0280	0.052*
H12B	0.5785	0.1421	−0.0210	0.052*
C13	0.3083 (4)	0.18340 (7)	0.1460 (3)	0.0472 (6)
H13A	0.2223	0.1635	0.0865	0.057*
H13B	0.2044	0.2038	0.1501	0.057*
C14	0.3970 (4)	0.17252 (6)	0.3390 (3)	0.0439 (5)
H14A	0.4768	0.1928	0.4006	0.053*
H14B	0.2676	0.1661	0.4064	0.053*
C15	0.4241 (5)	0.20357 (6)	−0.1491 (3)	0.0519 (6)
H15A	0.3210	0.1850	−0.2032	0.062*
H15B	0.5576	0.2045	−0.2184	0.062*
C16	0.3036 (6)	0.23880 (8)	−0.1657 (4)	0.0696 (8)
H16A	0.1483	0.2367	−0.1290	0.083*
H16B	0.3870	0.2568	−0.0892	0.083*
N1	0.8237 (3)	0.08156 (5)	0.7086 (2)	0.0419 (5)
N2	0.5552 (3)	0.14180 (5)	0.3366 (2)	0.0360 (4)
N3	0.5012 (3)	0.19317 (5)	0.0404 (2)	0.0403 (5)
O1	0.5199 (3)	0.04208 (5)	0.7274 (2)	0.0618 (5)
O2	1.1636 (3)	0.11320 (5)	0.7720 (3)	0.0648 (6)
O3	0.2965 (5)	0.24873 (7)	−0.3547 (3)	0.0921 (8)
H3A	0.2018	0.2650	−0.3766	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0419 (11)	0.0314 (10)	0.0381 (11)	0.0005 (8)	−0.0002 (9)	0.0024 (8)
C2	0.0529 (14)	0.0431 (12)	0.0443 (12)	−0.0071 (10)	−0.0002 (10)	0.0086 (10)
C3	0.0676 (16)	0.0493 (13)	0.0383 (12)	0.0031 (12)	−0.0014 (11)	0.0086 (10)
C4	0.0582 (15)	0.0584 (15)	0.0416 (13)	0.0088 (12)	−0.0115 (11)	0.0004 (11)
C5	0.0417 (12)	0.0526 (14)	0.0524 (14)	−0.0020 (10)	−0.0059 (10)	−0.0047 (11)
C6	0.0398 (11)	0.0342 (10)	0.0420 (12)	0.0016 (8)	0.0011 (9)	0.0001 (9)
C7	0.0434 (12)	0.0382 (11)	0.0473 (12)	−0.0015 (9)	0.0054 (10)	0.0020 (9)
C8	0.0452 (12)	0.0343 (11)	0.0432 (12)	−0.0016 (9)	−0.0034 (9)	0.0041 (9)
C9	0.0655 (15)	0.0407 (12)	0.0354 (11)	0.0044 (10)	0.0033 (10)	0.0052 (9)
C10	0.0457 (12)	0.0431 (12)	0.0310 (10)	0.0030 (9)	0.0059 (9)	0.0049 (8)
C11	0.0380 (11)	0.0497 (12)	0.0364 (11)	0.0053 (9)	0.0067 (9)	0.0062 (9)
C12	0.0481 (12)	0.0487 (13)	0.0335 (11)	0.0026 (10)	0.0076 (9)	0.0035 (9)
C13	0.0440 (12)	0.0513 (13)	0.0448 (13)	0.0093 (10)	−0.0025 (10)	0.0073 (10)
C14	0.0417 (12)	0.0531 (13)	0.0375 (12)	0.0081 (10)	0.0067 (9)	0.0072 (10)
C15	0.0728 (17)	0.0457 (13)	0.0350 (12)	0.0036 (12)	−0.0063 (11)	0.0025 (10)
C16	0.098 (2)	0.0624 (17)	0.0448 (14)	0.0265 (16)	−0.0084 (14)	0.0069 (12)
N1	0.0491 (11)	0.0367 (9)	0.0391 (10)	−0.0018 (8)	0.0011 (8)	0.0075 (8)
N2	0.0373 (9)	0.0403 (9)	0.0307 (9)	0.0014 (7)	0.0046 (7)	0.0047 (7)
N3	0.0502 (11)	0.0404 (10)	0.0291 (9)	−0.0017 (8)	−0.0018 (7)	0.0031 (7)
O1	0.0588 (11)	0.0610 (11)	0.0604 (11)	−0.0196 (9)	−0.0195 (9)	0.0150 (9)
O2	0.0597 (11)	0.0635 (11)	0.0720 (13)	−0.0211 (9)	0.0098 (9)	0.0157 (9)
O3	0.136 (2)	0.0818 (15)	0.0558 (12)	0.0490 (15)	−0.0048 (13)	0.0216 (11)

Geometric parameters (Å, º) top

C1—C2	1.379 (3)	C11—N2	1.460 (3)
C1—C6	1.381 (3)	C11—C12	1.508 (3)
C1—C8	1.487 (3)	C11—H11A	0.9700
C2—C3	1.385 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—N3	1.460 (3)
C3—C4	1.378 (4)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.387 (4)	C13—N3	1.470 (3)
C4—H4	0.9300	C13—C14	1.516 (3)
C5—C6	1.381 (3)	C13—H13A	0.9700
C5—H5	0.9300	C13—H13B	0.9700
C6—C7	1.489 (3)	C14—N2	1.463 (3)
C7—O2	1.204 (3)	C14—H14A	0.9700
C7—N1	1.395 (3)	C14—H14B	0.9700
C8—O1	1.210 (3)	C15—N3	1.472 (3)
C8—N1	1.385 (3)	C15—C16	1.479 (4)
C9—N1	1.456 (3)	C15—H15A	0.9700
C9—C10	1.515 (3)	C15—H15B	0.9700
C9—H9A	0.9700	C16—O3	1.435 (3)
C9—H9B	0.9700	C16—H16A	0.9700
C10—N2	1.459 (3)	C16—H16B	0.9700
C10—H10A	0.9700	O3—H3A	0.8200
C10—H10B	0.9700

C2—C1—C6	121.2 (2)	H11A—C11—H11B	108.1
C2—C1—C8	130.4 (2)	N3—C12—C11	110.60 (17)
C6—C1—C8	108.36 (18)	N3—C12—H12A	109.5
C1—C2—C3	117.4 (2)	C11—C12—H12A	109.5
C1—C2—H2	121.3	N3—C12—H12B	109.5
C3—C2—H2	121.3	C11—C12—H12B	109.5
C4—C3—C2	121.5 (2)	H12A—C12—H12B	108.1
C4—C3—H3	119.3	N3—C13—C14	110.70 (18)
C2—C3—H3	119.3	N3—C13—H13A	109.5
C3—C4—C5	121.1 (2)	C14—C13—H13A	109.5
C3—C4—H4	119.4	N3—C13—H13B	109.5
C5—C4—H4	119.4	C14—C13—H13B	109.5
C6—C5—C4	117.2 (2)	H13A—C13—H13B	108.1
C6—C5—H5	121.4	N2—C14—C13	110.55 (18)
C4—C5—H5	121.4	N2—C14—H14A	109.5
C5—C6—C1	121.6 (2)	C13—C14—H14A	109.5
C5—C6—C7	130.5 (2)	N2—C14—H14B	109.5
C1—C6—C7	107.87 (18)	C13—C14—H14B	109.5
O2—C7—N1	124.7 (2)	H14A—C14—H14B	108.1
O2—C7—C6	129.5 (2)	N3—C15—C16	114.0 (2)
N1—C7—C6	105.80 (18)	N3—C15—H15A	108.8
O1—C8—N1	125.2 (2)	C16—C15—H15A	108.8
O1—C8—C1	128.9 (2)	N3—C15—H15B	108.8
N1—C8—C1	105.84 (17)	C16—C15—H15B	108.8
N1—C9—C10	112.62 (18)	H15A—C15—H15B	107.7
N1—C9—H9A	109.1	O3—C16—C15	105.9 (2)
C10—C9—H9A	109.1	O3—C16—H16A	110.6
N1—C9—H9B	109.1	C15—C16—H16A	110.6
C10—C9—H9B	109.1	O3—C16—H16B	110.6
H9A—C9—H9B	107.8	C15—C16—H16B	110.6
N2—C10—C9	111.02 (17)	H16A—C16—H16B	108.7
N2—C10—H10A	109.4	C8—N1—C7	112.13 (18)
C9—C10—H10A	109.4	C8—N1—C9	124.43 (19)
N2—C10—H10B	109.4	C7—N1—C9	123.34 (19)
C9—C10—H10B	109.4	C11—N2—C10	111.95 (16)
H10A—C10—H10B	108.0	C11—N2—C14	108.56 (17)
N2—C11—C12	110.79 (18)	C10—N2—C14	110.22 (16)
N2—C11—H11A	109.5	C12—N3—C13	108.70 (17)
C12—C11—H11A	109.5	C12—N3—C15	109.44 (17)
N2—C11—H11B	109.5	C13—N3—C15	112.78 (18)
C12—C11—H11B	109.5	C16—O3—H3A	109.5

C6—C1—C2—C3	−0.8 (3)	O1—C8—N1—C7	−177.6 (2)
C8—C1—C2—C3	176.4 (2)	C1—C8—N1—C7	0.3 (2)
C1—C2—C3—C4	1.0 (4)	O1—C8—N1—C9	−1.1 (4)
C2—C3—C4—C5	−0.3 (4)	C1—C8—N1—C9	176.87 (19)
C3—C4—C5—C6	−0.4 (4)	O2—C7—N1—C8	179.9 (2)
C4—C5—C6—C1	0.5 (3)	C6—C7—N1—C8	−0.1 (2)
C4—C5—C6—C7	−177.1 (2)	O2—C7—N1—C9	3.2 (4)
C2—C1—C6—C5	0.1 (3)	C6—C7—N1—C9	−176.69 (19)
C8—C1—C6—C5	−177.7 (2)	C10—C9—N1—C8	97.9 (3)
C2—C1—C6—C7	178.2 (2)	C10—C9—N1—C7	−85.9 (3)
C8—C1—C6—C7	0.4 (2)	C12—C11—N2—C10	179.14 (17)
C5—C6—C7—O2	−2.3 (4)	C12—C11—N2—C14	−59.0 (2)
C1—C6—C7—O2	179.9 (2)	C9—C10—N2—C11	−69.7 (2)
C5—C6—C7—N1	177.6 (2)	C9—C10—N2—C14	169.38 (19)
C1—C6—C7—N1	−0.2 (2)	C13—C14—N2—C11	58.3 (2)
C2—C1—C8—O1	−0.1 (4)	C13—C14—N2—C10	−178.72 (18)
C6—C1—C8—O1	177.4 (2)	C11—C12—N3—C13	−58.2 (2)
C2—C1—C8—N1	−178.0 (2)	C11—C12—N3—C15	178.21 (19)
C6—C1—C8—N1	−0.4 (2)	C14—C13—N3—C12	57.8 (2)
N1—C9—C10—N2	−173.76 (18)	C14—C13—N3—C15	179.35 (18)
N2—C11—C12—N3	60.1 (2)	C16—C15—N3—C12	−168.0 (2)
N3—C13—C14—N2	−58.9 (3)	C16—C15—N3—C13	70.9 (3)
N3—C15—C16—O3	165.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N3ⁱ	0.82	2.00	2.811 (3)	171

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₁N₃O₃
M_r	303.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.8109 (6), 37.012 (4), 7.3537 (8)
β (°)	95.634 (2)
V (Å³)	1573.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.978, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	8562, 2775, 2537
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.161, 1.00
No. of reflections	2775
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.38

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), 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
O3—H3A···N3ⁱ	0.82	2.00	2.811 (3)	171

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

Acknowledgements

We gratefully acknowledge the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and Changzhou University (ZMF10020010) for financial support.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ghosh, B., Antonio, T., Zhen, J., Kharkar, P., Reith, M. E. A. & Dutta, A. K. (2010). J. Med. Chem. 53, 1023–1037. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tian, Z., Wei, X., Liang, J., Liu, R. & Zhang, Y. (2011). Yingyong Huagong, 40, 1648–1652. CAS Google Scholar