4-(2-{2-[2-(2-Nitro-1H-imidazol-1-yl)ethoxy]eth­oxy}eth­oxy)benzaldehyde

Li, S.-X.; Zhang, D.-H.; Fun, H.-K.; Hemamalini, M.

doi:10.1107/S1600536811014322

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1206

doi:10.1107/S1600536811014322

Open

access

4-(2-{2-[2-(2-Nitro-1H-imidazol-1-yl)ethoxy]ethoxy}ethoxy)benzaldehyde

Shu-Xian Li,^a ‡ Da-Hai Zhang,^a Hoong-Kun Fun ^b ^*§ and Madhukar Hemamalini ^b

^aDepartment of Chemistry, Handan College, Handan, Hebei Province 056005, People's Republic of China, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 11 April 2011; accepted 16 April 2011; online 22 April 2011)

In the molecule of the title compound, C₁₆H₁₉N₃O₆, the imidazole ring is essentially planar [maximum deviation = 0.002 (2) Å] and forms a dihedral angle of 5.08 (14)° with the nitro group. In the crystal structure, adjacent molecules are connected via intermolecular C—H⋯O hydrogen bonds into columns parallel to the a axis.

Related literature

For details and applications of nitroimidazole, see: Abdel-Jalil et al. (2006 ); Kennedy et al. (2006 ); Nagasawa et al. (2006 ); Nunn et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₉N₃O₆
M_r = 349.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.4403 (3) Å
b = 11.4686 (8) Å
c = 31.2763 (19) Å
V = 1592.72 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
1.00 × 0.10 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.895, T_max = 0.990
11825 measured reflections
2763 independent reflections
2243 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.094
S = 1.03
2763 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O4ⁱ	0.97	2.56	3.335 (3)	137
C10—H10A⋯O4ⁱⁱ	0.97	2.57	3.461 (3)	152
Symmetry codes: (i) $[x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014322/rz2583sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014322/rz2583Isup2.hkl

checkCIF report

Comment top

Nitroimidazole is an important building block in the design and synthesis of hypoxia makers (Abdel-Jalil et al. 2006; Kennedy et al. 2006, Nagasawa et al., 2006). In a normal cell, the nitroimidazole moiety undergoes reduction to become a potentially reactive species and can be reoxidized in the presence of normal oxygen levels. However in hypoxic tissues, the low oxygen concentration is not able to effectively reoxidize the molecule and this results in more reactive intermediates that bind with the components of hypoxic tissues (Nunn et al., 1995). In an attempt to develop new hypoxic cell radiosensitizers, we present herein the crystal structure of 4-(2-(2-(2-(2-nitro-1H-imidazol-1-yl) ethoxy)-ethoxy)ethoxy)benzaldehyde (I).

In (I), (Fig. 1), the imidazole group is essentially planar, with a maximum deviation of 0.002 (2) Å for atom N2. The nitro group is twisted from the mean plane of imidazole ring with torsion angles O5—N3—C15—N1 = -3.7 (3)° and O6—N3—C15—N1 = 176.7 (2)°. The conformation of the 1-(2-(2-ethoxy)ethoxy)ethyl)propane group is (-)-syn-clinal with respect to the imidazole ring, which is reflected by the torsion angle N1—C12—C11—O3 = -105.5 (2)°. The dihedral angle between the imidazole (N1–N2/C13–C15) ring and the benzene (C1–C6) ring is 38.60 (13)°. Bond distances and angles have normal values (Allen et al., 1987).

The crystal packing (Fig. 2) shows that the molecules are linked by weak intermolecular C9—H9B···O4 and C10—H10A···O4 (Table 1) hydrogen interactions into columns parallel to the a axis.

Related literature top

For details and applications of nitroimidazole, see: Abdel-Jalil et al. (2006); Kennedy et al. (2006); Nagasawa et al. (2006); Nunn et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of the 4-(2-(2-(2-(2-nitro-1H-imidazol-1-yl)ethoxy) ethoxy)ethyl-4-methylbenzenesulfonate (0.600 g, 1.5 mmol) and potassium carbonate (0.569 g, 4.1 mmol) in DMF (20 mL) was added a solution of 4-hydroxybenzaldehyde (0.166 g, 1.4 mmol) in DMF (10 ml) under argon atmosphere. The mixture was stirred at 120°C for 20 h. After concentration on the rotary evaporator under reduced pressure, ethyl acetate (80 ml) was then added to the reaction residue. The content was then washed with water (20 ml × 3), dried (Na₂SO₄) and the organic layer was evaporated to dryness and subjected to chromatography on silica with EtOAc–hexane (3:1 v/v) to afford the desired compound (I) (0.435 g, yield 89%). Analysis Calcd for C₁₆H₁₉N₃O₆: C 55.01, H 5.48, N 12.03%; found: C 55.31, H 4.91, N 12.43%. ¹H NMR (500 MHz, CDCl₃) δ: 3.66 (m, 4H), 3.86 (m, 4H), 4.22 (t, J = 4.5 Hz, 2H), 4.64 (t, J = 4.5 Hz, 2H), 7.04 (d, J = 9.0, 2H), 7.10 (s, 1H), 7.23 (s, 1H), 7.87 (d, J = 9.0 Hz, 2H), 9.91 (s, 1H). Single crystals of X-ray diffraction quality were prepared by the slow diffusion of hexane into a dichloromethane solution of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. H atoms non involved in hydrogen bonds are omitted.

4-(2-{2-[2-(2-Nitro-1H-imidazol-1-yl)ethoxy]ethoxy}ethoxy)benzaldehyde top

Crystal data top

C₁₆H₁₉N₃O₆	F(000) = 736
M_r = 349.34	D_x = 1.457 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3196 reflections
a = 4.4403 (3) Å	θ = 2.6–27.4°
b = 11.4686 (8) Å	µ = 0.11 mm⁻¹
c = 31.2763 (19) Å	T = 100 K
V = 1592.72 (18) Å³	Needle, colourless
Z = 4	1.00 × 0.10 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2763 independent reflections
Radiation source: fine-focus sealed tube	2243 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 30.2°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→5
T_min = 0.895, T_max = 0.990	k = −12→16
11825 measured reflections	l = −37→43

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0349P)² + 0.4321P] where P = (F_o² + 2F_c²)/3
2763 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₉N₃O₆	V = 1592.72 (18) Å³
M_r = 349.34	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.4403 (3) Å	µ = 0.11 mm⁻¹
b = 11.4686 (8) Å	T = 100 K
c = 31.2763 (19) Å	1.00 × 0.10 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2763 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2243 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.990	R_int = 0.045
11825 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
2763 reflections	Δρ_min = −0.22 e Å⁻³
226 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.9164 (4)	0.80126 (13)	0.06764 (4)	0.0200 (4)
O2	1.0360 (4)	0.59396 (12)	0.11489 (4)	0.0195 (3)
O3	0.9292 (4)	0.36579 (13)	0.15473 (4)	0.0219 (4)
O4	0.0201 (4)	1.14948 (13)	−0.02814 (5)	0.0258 (4)
O5	0.3451 (4)	0.06021 (15)	0.17441 (5)	0.0295 (4)
O6	0.5051 (5)	−0.10825 (14)	0.19678 (5)	0.0339 (5)
N1	0.7409 (5)	0.17301 (15)	0.22943 (5)	0.0195 (4)
N2	0.8668 (5)	−0.00344 (17)	0.25495 (6)	0.0243 (5)
N3	0.5073 (5)	−0.00129 (17)	0.19754 (5)	0.0243 (4)
C1	0.6176 (6)	0.87874 (18)	0.01331 (7)	0.0193 (5)
H1A	0.6778	0.8169	−0.0039	0.023*
C2	0.4203 (6)	0.96061 (18)	−0.00235 (7)	0.0193 (5)
H2A	0.3471	0.9536	−0.0301	0.023*
C3	0.3288 (5)	1.05450 (19)	0.02312 (7)	0.0190 (5)
C4	0.4436 (6)	1.06324 (19)	0.06456 (7)	0.0210 (5)
H4A	0.3840	1.1252	0.0818	0.025*
C5	0.6446 (6)	0.98164 (19)	0.08066 (7)	0.0201 (5)
H5A	0.7222	0.9893	0.1081	0.024*
C6	0.7279 (5)	0.88797 (18)	0.05488 (7)	0.0178 (5)
C7	1.0208 (6)	0.80108 (18)	0.11112 (6)	0.0202 (5)
H7A	0.8515	0.7973	0.1307	0.024*
H7B	1.1339	0.8716	0.1171	0.024*
C8	1.2175 (6)	0.69626 (19)	0.11638 (7)	0.0207 (5)
H8A	1.3665	0.6940	0.0937	0.025*
H8B	1.3226	0.7002	0.1435	0.025*
C9	1.2191 (6)	0.4924 (2)	0.11083 (7)	0.0214 (5)
H9A	1.3631	0.4893	0.1341	0.026*
H9B	1.3299	0.4952	0.0841	0.026*
C10	1.0220 (6)	0.38626 (18)	0.11178 (6)	0.0202 (5)
H10A	0.8471	0.3982	0.0937	0.024*
H10B	1.1322	0.3193	0.1011	0.024*
C11	0.7292 (6)	0.27044 (19)	0.15794 (7)	0.0224 (5)
H11A	0.8336	0.1984	0.1514	0.027*
H11B	0.5644	0.2797	0.1378	0.027*
C12	0.6082 (7)	0.26698 (19)	0.20368 (7)	0.0243 (6)
H12A	0.6493	0.3411	0.2174	0.029*
H12B	0.3914	0.2568	0.2028	0.029*
C13	0.9408 (6)	0.1895 (2)	0.26212 (7)	0.0242 (5)
H13A	1.0129	0.2605	0.2721	0.029*
C14	1.0146 (7)	0.0807 (2)	0.27736 (7)	0.0264 (5)
H14A	1.1469	0.0666	0.2998	0.032*
C15	0.7066 (6)	0.05487 (19)	0.22695 (6)	0.0204 (5)
C16	0.1127 (6)	1.14220 (19)	0.00810 (7)	0.0213 (5)
H16A	0.0418	1.1961	0.0279	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0253 (9)	0.0186 (7)	0.0161 (7)	0.0025 (8)	0.0000 (7)	−0.0003 (6)
O2	0.0184 (8)	0.0159 (7)	0.0243 (7)	−0.0011 (7)	0.0010 (8)	0.0014 (6)
O3	0.0291 (10)	0.0198 (7)	0.0168 (7)	−0.0051 (8)	−0.0008 (7)	−0.0001 (6)
O4	0.0266 (10)	0.0266 (8)	0.0242 (8)	0.0009 (8)	−0.0027 (8)	0.0016 (6)
O5	0.0294 (10)	0.0345 (9)	0.0245 (8)	−0.0009 (9)	−0.0035 (8)	0.0016 (7)
O6	0.0496 (13)	0.0188 (8)	0.0333 (9)	−0.0068 (9)	0.0004 (11)	−0.0028 (7)
N1	0.0239 (11)	0.0163 (9)	0.0184 (9)	0.0011 (8)	0.0026 (9)	0.0005 (7)
N2	0.0337 (12)	0.0194 (9)	0.0200 (9)	0.0019 (10)	0.0030 (9)	0.0025 (7)
N3	0.0303 (12)	0.0233 (9)	0.0193 (8)	−0.0045 (10)	0.0044 (10)	0.0002 (8)
C1	0.0225 (12)	0.0159 (10)	0.0195 (10)	−0.0018 (10)	0.0037 (10)	−0.0024 (8)
C2	0.0185 (12)	0.0220 (10)	0.0174 (9)	−0.0025 (10)	0.0001 (9)	0.0003 (8)
C3	0.0175 (11)	0.0182 (10)	0.0214 (10)	−0.0024 (10)	0.0023 (10)	0.0005 (8)
C4	0.0235 (12)	0.0179 (10)	0.0216 (10)	0.0008 (11)	0.0004 (10)	−0.0033 (8)
C5	0.0243 (13)	0.0197 (10)	0.0165 (9)	−0.0024 (10)	−0.0008 (10)	−0.0018 (8)
C6	0.0182 (11)	0.0148 (10)	0.0205 (10)	−0.0016 (10)	0.0034 (10)	0.0027 (8)
C7	0.0245 (13)	0.0191 (10)	0.0170 (9)	−0.0026 (11)	0.0000 (11)	0.0004 (8)
C8	0.0198 (12)	0.0200 (10)	0.0222 (10)	−0.0042 (10)	−0.0006 (11)	0.0005 (9)
C9	0.0224 (12)	0.0190 (10)	0.0227 (10)	0.0035 (11)	−0.0003 (11)	−0.0009 (9)
C10	0.0251 (13)	0.0157 (10)	0.0199 (10)	0.0021 (10)	−0.0012 (11)	−0.0002 (8)
C11	0.0300 (14)	0.0151 (10)	0.0220 (11)	−0.0005 (10)	−0.0028 (12)	0.0028 (9)
C12	0.0314 (15)	0.0157 (10)	0.0258 (11)	0.0037 (11)	0.0012 (11)	0.0029 (9)
C13	0.0268 (13)	0.0272 (11)	0.0185 (10)	−0.0019 (12)	0.0027 (11)	−0.0034 (9)
C14	0.0333 (14)	0.0273 (11)	0.0185 (10)	0.0009 (12)	0.0006 (12)	0.0000 (9)
C15	0.0270 (13)	0.0169 (10)	0.0174 (10)	−0.0017 (10)	0.0027 (10)	−0.0010 (8)
C16	0.0193 (12)	0.0172 (10)	0.0274 (11)	−0.0024 (10)	0.0010 (11)	0.0005 (9)

Geometric parameters (Å, º) top

O1—C6	1.360 (3)	C4—H4A	0.9300
O1—C7	1.437 (2)	C5—C6	1.393 (3)
O2—C8	1.424 (3)	C5—H5A	0.9300
O2—C9	1.426 (3)	C7—C8	1.495 (3)
O3—C11	1.412 (3)	C7—H7A	0.9700
O3—C10	1.425 (2)	C7—H7B	0.9700
O4—C16	1.209 (3)	C8—H8A	0.9700
O5—N3	1.241 (3)	C8—H8B	0.9700
O6—N3	1.227 (2)	C9—C10	1.500 (3)
N1—C15	1.366 (3)	C9—H9A	0.9700
N1—C13	1.367 (3)	C9—H9B	0.9700
N1—C12	1.469 (3)	C10—H10A	0.9700
N2—C15	1.312 (3)	C10—H10B	0.9700
N2—C14	1.361 (3)	C11—C12	1.529 (3)
N3—C15	1.429 (3)	C11—H11A	0.9700
C1—C2	1.374 (3)	C11—H11B	0.9700
C1—C6	1.393 (3)	C12—H12A	0.9700
C1—H1A	0.9300	C12—H12B	0.9700
C2—C3	1.400 (3)	C13—C14	1.375 (3)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.396 (3)	C14—H14A	0.9300
C3—C16	1.467 (3)	C16—H16A	0.9300
C4—C5	1.388 (3)

C6—O1—C7	118.52 (17)	C7—C8—H8B	109.8
C8—O2—C9	110.66 (17)	H8A—C8—H8B	108.3
C11—O3—C10	112.10 (16)	O2—C9—C10	109.2 (2)
C15—N1—C13	104.60 (19)	O2—C9—H9A	109.8
C15—N1—C12	130.7 (2)	C10—C9—H9A	109.8
C13—N1—C12	124.70 (19)	O2—C9—H9B	109.8
C15—N2—C14	104.12 (19)	C10—C9—H9B	109.8
O6—N3—O5	123.5 (2)	H9A—C9—H9B	108.3
O6—N3—C15	117.9 (2)	O3—C10—C9	108.74 (17)
O5—N3—C15	118.57 (18)	O3—C10—H10A	109.9
C2—C1—C6	120.3 (2)	C9—C10—H10A	109.9
C2—C1—H1A	119.8	O3—C10—H10B	109.9
C6—C1—H1A	119.8	C9—C10—H10B	109.9
C1—C2—C3	120.5 (2)	H10A—C10—H10B	108.3
C1—C2—H2A	119.7	O3—C11—C12	107.91 (18)
C3—C2—H2A	119.7	O3—C11—H11A	110.1
C4—C3—C2	118.5 (2)	C12—C11—H11A	110.1
C4—C3—C16	119.1 (2)	O3—C11—H11B	110.1
C2—C3—C16	122.4 (2)	C12—C11—H11B	110.1
C5—C4—C3	121.5 (2)	H11A—C11—H11B	108.4
C5—C4—H4A	119.2	N1—C12—C11	113.03 (19)
C3—C4—H4A	119.2	N1—C12—H12A	109.0
C4—C5—C6	118.7 (2)	C11—C12—H12A	109.0
C4—C5—H5A	120.6	N1—C12—H12B	109.0
C6—C5—H5A	120.6	C11—C12—H12B	109.0
O1—C6—C5	123.9 (2)	H12A—C12—H12B	107.8
O1—C6—C1	115.77 (19)	N1—C13—C14	106.8 (2)
C5—C6—C1	120.3 (2)	N1—C13—H13A	126.6
O1—C7—C8	107.08 (17)	C14—C13—H13A	126.6
O1—C7—H7A	110.3	N2—C14—C13	110.5 (2)
C8—C7—H7A	110.3	N2—C14—H14A	124.8
O1—C7—H7B	110.3	C13—C14—H14A	124.8
C8—C7—H7B	110.3	N2—C15—N1	114.0 (2)
H7A—C7—H7B	108.6	N2—C15—N3	122.39 (19)
O2—C8—C7	109.2 (2)	N1—C15—N3	123.6 (2)
O2—C8—H8A	109.8	O4—C16—C3	124.7 (2)
C7—C8—H8A	109.8	O4—C16—H16A	117.6
O2—C8—H8B	109.9	C3—C16—H16A	117.6

C6—C1—C2—C3	0.3 (3)	C15—N1—C12—C11	−69.6 (3)
C1—C2—C3—C4	0.3 (3)	C13—N1—C12—C11	108.9 (2)
C1—C2—C3—C16	−178.4 (2)	O3—C11—C12—N1	−105.5 (2)
C2—C3—C4—C5	0.1 (3)	C15—N1—C13—C14	0.0 (3)
C16—C3—C4—C5	178.9 (2)	C12—N1—C13—C14	−178.9 (2)
C3—C4—C5—C6	−1.2 (3)	C15—N2—C14—C13	−0.3 (3)
C7—O1—C6—C5	4.4 (3)	N1—C13—C14—N2	0.2 (3)
C7—O1—C6—C1	−175.6 (2)	C14—N2—C15—N1	0.3 (3)
C4—C5—C6—O1	−178.2 (2)	C14—N2—C15—N3	−177.8 (2)
C4—C5—C6—C1	1.9 (3)	C13—N1—C15—N2	−0.1 (3)
C2—C1—C6—O1	178.6 (2)	C12—N1—C15—N2	178.6 (2)
C2—C1—C6—C5	−1.4 (3)	C13—N1—C15—N3	177.9 (2)
C6—O1—C7—C8	179.05 (18)	C12—N1—C15—N3	−3.3 (4)
C9—O2—C8—C7	167.89 (17)	O6—N3—C15—N2	−5.4 (3)
O1—C7—C8—O2	−70.0 (2)	O5—N3—C15—N2	174.2 (2)
C8—O2—C9—C10	176.92 (17)	O6—N3—C15—N1	176.7 (2)
C11—O3—C10—C9	176.86 (19)	O5—N3—C15—N1	−3.7 (3)
O2—C9—C10—O3	−75.8 (2)	C4—C3—C16—O4	172.9 (2)
C10—O3—C11—C12	−171.84 (19)	C2—C3—C16—O4	−8.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O4ⁱ	0.97	2.56	3.335 (3)	137
C10—H10A···O4ⁱⁱ	0.97	2.57	3.461 (3)	152

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉N₃O₆
M_r	349.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	4.4403 (3), 11.4686 (8), 31.2763 (19)
V (Å³)	1592.72 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	1.00 × 0.10 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.895, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	11825, 2763, 2243
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.094, 1.03
No. of reflections	2763
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
C9—H9B···O4ⁱ	0.9700	2.5600	3.335 (3)	137.40
C10—H10A···O4ⁱⁱ	0.9700	2.5700	3.461 (3)	152.40

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

Footnotes

‡Additional correspondence author, e-mail: 13722380143@163.com.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

SXL and DHZ gratefully acknowledge the financial assistance of Handan College. The authors thank the Malaysian Government and Universiti Sains Malaysia for Scientific Advancement Grant Allocation (SAGA) grant No. 304/PFIZIK/653003/A118. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

Abdel-Jalil, R. J. M., Übele, M., Ehrlichmann, W., Voelter, W. & Machulla, H. J. (2006). J. Radioanal. Nucl. Chem. 267, 557–560. Web of Science CrossRef CAS Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kennedy, D. C., Wu, A., Patrick, B. O. & James, B. R. (2006). J. Inorg. Biochem. 100, 1974–1982. Web of Science CSD CrossRef PubMed CAS Google Scholar
Nagasawa, H., Uto, Y., Kirk, K. L. & Hori, H. (2006). Biol. Pharm. Bull. 29, 2335–2342. Web of Science CrossRef PubMed CAS Google Scholar
Nunn, A., Linder, K. & Strauss, W. H. (1995). J. Nucl. Med. pp. 264–280. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar