4,4,5,5-Tetra­methyl-2-(3,4,5-trimethoxy­phen­yl)imidazolidine-1-oxyl 3-oxide

Wang, H.-B.; Jing, L.-L.; Gao, P.; Sun, X.-L.

doi:10.1107/S1600536809029274

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2090

doi:10.1107/S1600536809029274

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4,4,5,5-Tetramethyl-2-(3,4,5-trimethoxyphenyl)imidazolidine-1-oxyl 3-oxide

Hai-Bo Wang,^a Lin-Lin Jing,^a Peng Gao ^a and Xiao-Li Sun ^a ^*

^aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China
^*Correspondence e-mail: lisydcn@yahoo.com.cn

(Received 26 June 2009; accepted 23 July 2009; online 8 August 2009)

In the title nitronyl nitroxide radical compound, C₁₆C₂₃N₂O₅, the imidazole and benzene rings are twisted with respect to each other, making a dihedral angle of 26.2 (4)°. The imidazole ring adopts a half-chair conformation. Weak C—H⋯π interactions are also found.

Related literature

For the preparation of the title compound see: Ullman et al. (1974 ). For related structures, see: Feher et al. (2008 ); Gao et al. (2009 ); Qin et al. (2009 ); Cirujeda et al. (1995 ); Matsushita et al. (1997 ). For the coordination properties of the title compound and its use in the formation of molecule-based magnetic materials, see: Takui et al. (2009 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₂₃N₂O₅
M_r = 323.36
Orthorhombic, P b c a
a = 20.623 (3) Å
b = 7.2168 (12) Å
c = 22.831 (4) Å
V = 3398.0 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.32 × 0.25 × 0.17 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: none
15858 measured reflections
3027 independent reflections
1519 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.119
S = 1.06
3027 reflections
216 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯Cg2ⁱ	0.96	2.80	3.644 (2)	147
Symmetry code: (i) -x, -y, -z+1. Cg2 is the centroid of the phenyl ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029274/dn2472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029274/dn2472Isup2.hkl

checkCIF report

Comment top

The title radical compound was obtained from the oxidation of 4,4,5,5- tetramethyl-2-(3,4,5-trimethoxybenzenyl)-imidazolidine-1,3-diol, which was prepared by the condensation of 3,4,5-trimethoxybenzaldehyde with 2,3-Dimethyl-2,3-bis(hydroxyl-amino)butane. The title compound was used for coordination with many metal cations, such as Mn²⁺, Cu²⁺, and Ni²⁺, in order to form some molecule-based magnetic materials (Takui et al., 2009).

The molecular structure of the title compound is shown in Fig 1. Examination of bond length within the five membered rings shows an average structure as observed with related compounds (Cirujeda et al., 1995; Feher et al., 2008; Gao et al., 2009; Matsushita et al., 1997; Qin et al., 2009).

The imidazole and the phenyl rings are twisted with respect to each other making a dihedral angle of 26.2 (4)°. The imidazole ring has an half-chair conformation with puckering parameters O(2)=. 0.0275 (2)Å and ϕ= 233.0 (5)°(Cremer & Pople, 1975). The crystal structure is stabilized by weak C—H···π (Table 1, Cg2 is the centroid of the phenyl ring) and van der Waals interactions.

Related literature top

For the preparation of the title compound see: Ullman et al. (1974). For related structures, see: Feher et al. (2008); Gao et al. (2009); Qin et al. (2009); Cirujeda et al. (1995); Matsushita et al. (1997). For coordination properties of the the title compound and its use in the formation of molecule-based magnetic materials, see: Takui et al. (2009). For puckering parameters, see: Cremer & Pople (1975). Cg2 is the centroid of the phenyl ring

Experimental top

The compound 4,4,5,5-tetramethyl-2-(3,4,5-trimethoxybenzenyl)-imidazolidine -1-oxyl-3-oxide was prepared according to the method reported by Ullman et al. (1974). 2,3-Dimethyl-2,3-bis(hydroxylamino) butane (1.48 g, 10.0 mmol) and 3,4,5-trimethoxybenzaldehyde (1.96 g, 10.0 mmol) were dissolved in a methanol-water mixture (2:1), which was stirred for 5 h at reflux temperature, then cooled to room temperature and filtered. The white powder was washed by methanol. This product was dried under vaccum, then, it was suspended in dichloromethane (50.0 ml) and the water solution (30.0 ml) of NaIO₄(1.7 g) was added and stirred at ice bath for 20 min. The reaction mixture was extracted by dichloromethane (30.0 ml) for twice and the organic layer was combined and dried over Na₂SO₄. Then the solvent was removed to give a dark blue residue which was purified by a flash column chromatography (eluent, ether and petroleum ether, the ratio of volume is 2 to 1) to yield the title compound (I) as a dark blue powder. Single crystals of compound (I) were obtained from the mixed solution of n-heptane and dichloromethane (the ratio of volume is 1 to 1).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound (I), showing the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.

4,4,5,5-Tetramethyl-2-(3,4,5-trimethoxyphenyl)imidazolidine-1-oxyl 3-oxide top

Crystal data top

C₁₆H₂₃N₂O₅	F(000) = 1384
M_r = 323.36	D_x = 1.264 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1322 reflections
a = 20.623 (3) Å	θ = 3.1–18.2°
b = 7.2168 (12) Å	µ = 0.09 mm⁻¹
c = 22.831 (4) Å	T = 296 K
V = 3398.0 (10) Å³	Block, blue
Z = 8	0.32 × 0.25 × 0.17 mm

Data collection top

Bruker SMART APEX2 diffractometer	1519 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 25.1°, θ_min = 1.8°
Detector resolution: 0 pixels mm^-1	h = −12→24
ϕ and ω scans	k = −8→8
15858 measured reflections	l = −27→26
3027 independent 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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3027 reflections	Δρ_max = 0.17 e Å⁻³
216 parameters	Δρ_min = −0.23 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: 0.0019 (5)

Crystal data top

C₁₆H₂₃N₂O₅	V = 3398.0 (10) Å³
M_r = 323.36	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 20.623 (3) Å	µ = 0.09 mm⁻¹
b = 7.2168 (12) Å	T = 296 K
c = 22.831 (4) Å	0.32 × 0.25 × 0.17 mm

Data collection top

Bruker SMART APEX2 diffractometer	1519 reflections with I > 2σ(I)
15858 measured reflections	R_int = 0.062
3027 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.06	Δρ_max = 0.17 e Å⁻³
3027 reflections	Δρ_min = −0.23 e Å⁻³
216 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	0.06793 (9)	0.2073 (3)	0.49665 (8)	0.0570 (5)
N2	0.15280 (9)	0.0432 (3)	0.47376 (8)	0.0576 (5)
O1	0.01712 (9)	0.2652 (3)	0.52296 (7)	0.0913 (6)
O2	0.20243 (8)	−0.0630 (3)	0.47707 (7)	0.0903 (6)
O3	0.07153 (8)	0.1394 (2)	0.72841 (6)	0.0717 (5)
O4	0.12645 (7)	−0.1894 (2)	0.74689 (6)	0.0720 (5)
O5	0.17240 (8)	−0.3947 (2)	0.65885 (7)	0.0743 (5)
C1	0.08745 (10)	0.2830 (3)	0.43780 (9)	0.0511 (6)
C2	0.13132 (10)	0.1227 (3)	0.41649 (9)	0.0548 (6)
C3	0.11082 (10)	0.0839 (3)	0.51744 (9)	0.0506 (6)
C4	0.11306 (10)	0.0103 (3)	0.57690 (9)	0.0505 (6)
C5	0.14140 (10)	−0.1615 (3)	0.58697 (10)	0.0533 (6)
H5	0.1574	−0.2313	0.5559	0.064*
C6	0.14551 (10)	−0.2276 (3)	0.64375 (10)	0.0550 (6)
C7	0.12210 (10)	−0.1231 (3)	0.69035 (10)	0.0542 (6)
C8	0.09320 (11)	0.0479 (3)	0.67984 (9)	0.0543 (6)
C9	0.08840 (10)	0.1132 (3)	0.62324 (9)	0.0539 (6)
H9	0.0686	0.2266	0.6161	0.065*
C10	0.03918 (13)	0.3130 (4)	0.71996 (10)	0.0823 (8)
H10A	0.0693	0.4022	0.7047	0.123*
H10B	0.0224	0.3562	0.7567	0.123*
H10C	0.0041	0.2971	0.6928	0.123*
C11	0.18747 (13)	−0.1598 (5)	0.77318 (11)	0.1017 (10)
H11A	0.2203	−0.2234	0.7511	0.153*
H11B	0.1868	−0.2064	0.8126	0.153*
H11C	0.1968	−0.0295	0.7737	0.153*
C12	0.19952 (13)	−0.5035 (4)	0.61337 (12)	0.0869 (8)
H12A	0.1663	−0.5354	0.5857	0.130*
H12B	0.2177	−0.6146	0.6296	0.130*
H12C	0.2329	−0.4343	0.5940	0.130*
C13	0.12386 (12)	0.4629 (3)	0.45043 (11)	0.0726 (7)
H13A	0.0965	0.5449	0.4724	0.109*
H13B	0.1358	0.5209	0.4141	0.109*
H13C	0.1622	0.4360	0.4727	0.109*
C14	0.02814 (11)	0.3224 (3)	0.40075 (10)	0.0722 (7)
H14A	0.0019	0.2129	0.3984	0.108*
H14B	0.0414	0.3586	0.3621	0.108*
H14C	0.0035	0.4207	0.4183	0.108*
C15	0.18983 (12)	0.1816 (4)	0.38065 (10)	0.0783 (8)
H15A	0.2168	0.2619	0.4037	0.117*
H15B	0.1756	0.2462	0.3462	0.117*
H15C	0.2141	0.0739	0.3694	0.117*
C16	0.09402 (13)	−0.0316 (3)	0.38572 (10)	0.0765 (8)
H16A	0.1214	−0.1385	0.3818	0.115*
H16B	0.0808	0.0099	0.3476	0.115*
H16C	0.0564	−0.0633	0.4084	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0488 (12)	0.0639 (13)	0.0583 (12)	0.0123 (10)	0.0125 (10)	0.0033 (10)
N2	0.0509 (11)	0.0636 (13)	0.0583 (13)	0.0127 (11)	0.0095 (10)	0.0047 (10)
O1	0.0890 (14)	0.1057 (15)	0.0792 (11)	0.0366 (11)	0.0233 (11)	0.0175 (10)
O2	0.0745 (12)	0.1091 (15)	0.0872 (12)	0.0401 (11)	0.0215 (10)	0.0192 (10)
O3	0.0827 (13)	0.0798 (12)	0.0526 (10)	0.0157 (10)	0.0074 (8)	−0.0006 (9)
O4	0.0655 (12)	0.0913 (13)	0.0591 (11)	−0.0002 (9)	−0.0019 (9)	0.0204 (9)
O5	0.0798 (12)	0.0648 (12)	0.0783 (11)	0.0196 (10)	0.0001 (10)	0.0135 (10)
C1	0.0527 (14)	0.0518 (15)	0.0487 (13)	0.0028 (12)	0.0001 (11)	0.0055 (11)
C2	0.0590 (15)	0.0580 (15)	0.0474 (13)	0.0022 (12)	0.0058 (11)	0.0036 (12)
C3	0.0454 (13)	0.0516 (14)	0.0548 (14)	0.0060 (12)	0.0035 (12)	0.0021 (11)
C4	0.0450 (13)	0.0560 (15)	0.0504 (14)	−0.0007 (12)	0.0011 (11)	0.0049 (12)
C5	0.0475 (14)	0.0561 (16)	0.0561 (15)	0.0046 (11)	0.0013 (11)	−0.0007 (12)
C6	0.0453 (14)	0.0575 (16)	0.0623 (16)	0.0001 (12)	−0.0007 (12)	0.0082 (13)
C7	0.0478 (14)	0.0651 (17)	0.0496 (14)	−0.0037 (13)	0.0000 (11)	0.0112 (13)
C8	0.0517 (14)	0.0636 (16)	0.0474 (15)	−0.0029 (13)	0.0051 (11)	−0.0016 (12)
C9	0.0533 (14)	0.0544 (14)	0.0539 (15)	0.0038 (12)	0.0032 (11)	0.0032 (12)
C10	0.096 (2)	0.081 (2)	0.0701 (16)	0.0165 (17)	0.0143 (15)	−0.0100 (15)
C11	0.089 (2)	0.144 (3)	0.0727 (17)	−0.012 (2)	−0.0241 (17)	0.0182 (18)
C12	0.087 (2)	0.0655 (18)	0.108 (2)	0.0200 (15)	0.0072 (18)	0.0042 (16)
C13	0.0812 (19)	0.0569 (16)	0.0797 (17)	−0.0028 (14)	0.0029 (14)	0.0004 (13)
C14	0.0669 (17)	0.0819 (19)	0.0679 (15)	0.0090 (14)	−0.0072 (13)	0.0070 (14)
C15	0.0740 (19)	0.087 (2)	0.0736 (16)	0.0027 (15)	0.0289 (14)	0.0119 (14)
C16	0.097 (2)	0.0662 (17)	0.0662 (16)	−0.0037 (15)	−0.0008 (15)	−0.0077 (13)

Geometric parameters (Å, º) top

N1—O1	1.278 (2)	C8—C9	1.379 (3)
N1—C3	1.342 (2)	C9—H9	0.9300
N1—C1	1.506 (3)	C10—H10A	0.9600
N2—O2	1.281 (2)	C10—H10B	0.9600
N2—C3	1.353 (2)	C10—H10C	0.9600
N2—C2	1.495 (3)	C11—H11A	0.9600
O3—C8	1.366 (2)	C11—H11B	0.9600
O3—C10	1.433 (3)	C11—H11C	0.9600
O4—C7	1.380 (2)	C12—H12A	0.9600
O4—C11	1.410 (3)	C12—H12B	0.9600
O5—C6	1.372 (3)	C12—H12C	0.9600
O5—C12	1.417 (3)	C13—H13A	0.9600
C1—C14	1.514 (3)	C13—H13B	0.9600
C1—C13	1.527 (3)	C13—H13C	0.9600
C1—C2	1.547 (3)	C14—H14A	0.9600
C2—C15	1.519 (3)	C14—H14B	0.9600
C2—C16	1.525 (3)	C14—H14C	0.9600
C3—C4	1.459 (3)	C15—H15A	0.9600
C4—C9	1.389 (3)	C15—H15B	0.9600
C4—C5	1.390 (3)	C15—H15C	0.9600
C5—C6	1.384 (3)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.391 (3)	C16—H16C	0.9600
C7—C8	1.391 (3)

O1—N1—C3	126.26 (18)	O3—C10—H10A	109.5
O1—N1—C1	121.31 (18)	O3—C10—H10B	109.5
C3—N1—C1	112.36 (17)	H10A—C10—H10B	109.5
O2—N2—C3	126.70 (19)	O3—C10—H10C	109.5
O2—N2—C2	121.20 (17)	H10A—C10—H10C	109.5
C3—N2—C2	111.83 (17)	H10B—C10—H10C	109.5
C8—O3—C10	117.76 (17)	O4—C11—H11A	109.5
C7—O4—C11	113.82 (18)	O4—C11—H11B	109.5
C6—O5—C12	117.56 (18)	H11A—C11—H11B	109.5
N1—C1—C14	110.53 (17)	O4—C11—H11C	109.5
N1—C1—C13	105.77 (17)	H11A—C11—H11C	109.5
C14—C1—C13	110.08 (19)	H11B—C11—H11C	109.5
N1—C1—C2	99.52 (16)	O5—C12—H12A	109.5
C14—C1—C2	115.92 (18)	O5—C12—H12B	109.5
C13—C1—C2	114.05 (18)	H12A—C12—H12B	109.5
N2—C2—C15	110.07 (18)	O5—C12—H12C	109.5
N2—C2—C16	105.78 (18)	H12A—C12—H12C	109.5
C15—C2—C16	110.91 (19)	H12B—C12—H12C	109.5
N2—C2—C1	100.67 (16)	C1—C13—H13A	109.5
C15—C2—C1	115.15 (19)	C1—C13—H13B	109.5
C16—C2—C1	113.33 (18)	H13A—C13—H13B	109.5
N1—C3—N2	107.77 (18)	C1—C13—H13C	109.5
N1—C3—C4	126.3 (2)	H13A—C13—H13C	109.5
N2—C3—C4	125.9 (2)	H13B—C13—H13C	109.5
C9—C4—C5	120.32 (19)	C1—C14—H14A	109.5
C9—C4—C3	120.2 (2)	C1—C14—H14B	109.5
C5—C4—C3	119.5 (2)	H14A—C14—H14B	109.5
C6—C5—C4	119.2 (2)	C1—C14—H14C	109.5
C6—C5—H5	120.4	H14A—C14—H14C	109.5
C4—C5—H5	120.4	H14B—C14—H14C	109.5
O5—C6—C5	124.3 (2)	C2—C15—H15A	109.5
O5—C6—C7	115.1 (2)	C2—C15—H15B	109.5
C5—C6—C7	120.6 (2)	H15A—C15—H15B	109.5
O4—C7—C6	120.4 (2)	C2—C15—H15C	109.5
O4—C7—C8	119.8 (2)	H15A—C15—H15C	109.5
C6—C7—C8	119.9 (2)	H15B—C15—H15C	109.5
O3—C8—C9	124.9 (2)	C2—C16—H16A	109.5
O3—C8—C7	115.40 (19)	C2—C16—H16B	109.5
C9—C8—C7	119.7 (2)	H16A—C16—H16B	109.5
C8—C9—C4	120.3 (2)	C2—C16—H16C	109.5
C8—C9—H9	119.8	H16A—C16—H16C	109.5
C4—C9—H9	119.8	H16B—C16—H16C	109.5

O1—N1—C1—C14	−36.5 (3)	C2—N2—C3—C4	172.4 (2)
C3—N1—C1—C14	146.39 (19)	N1—C3—C4—C9	−26.4 (3)
O1—N1—C1—C13	82.7 (2)	N2—C3—C4—C9	151.8 (2)
C3—N1—C1—C13	−94.5 (2)	N1—C3—C4—C5	155.1 (2)
O1—N1—C1—C2	−158.87 (19)	N2—C3—C4—C5	−26.7 (3)
C3—N1—C1—C2	24.0 (2)	C9—C4—C5—C6	−0.9 (3)
O2—N2—C2—C15	−40.2 (3)	C3—C4—C5—C6	177.65 (19)
C3—N2—C2—C15	145.36 (19)	C12—O5—C6—C5	2.1 (3)
O2—N2—C2—C16	79.7 (2)	C12—O5—C6—C7	−177.4 (2)
C3—N2—C2—C16	−94.8 (2)	C4—C5—C6—O5	−179.98 (19)
O2—N2—C2—C1	−162.2 (2)	C4—C5—C6—C7	−0.5 (3)
C3—N2—C2—C1	23.4 (2)	C11—O4—C7—C6	82.3 (3)
N1—C1—C2—N2	−25.95 (19)	C11—O4—C7—C8	−98.7 (3)
C14—C1—C2—N2	−144.43 (19)	O5—C6—C7—O4	−0.3 (3)
C13—C1—C2—N2	86.2 (2)	C5—C6—C7—O4	−179.84 (19)
N1—C1—C2—C15	−144.27 (19)	O5—C6—C7—C8	−179.30 (19)
C14—C1—C2—C15	97.3 (2)	C5—C6—C7—C8	1.2 (3)
C13—C1—C2—C15	−32.1 (3)	C10—O3—C8—C9	2.5 (3)
N1—C1—C2—C16	86.5 (2)	C10—O3—C8—C7	−177.7 (2)
C14—C1—C2—C16	−31.9 (3)	O4—C7—C8—O3	0.7 (3)
C13—C1—C2—C16	−161.33 (18)	C6—C7—C8—O3	179.72 (19)
O1—N1—C3—N2	172.6 (2)	O4—C7—C8—C9	−179.5 (2)
C1—N1—C3—N2	−10.4 (2)	C6—C7—C8—C9	−0.5 (3)
O1—N1—C3—C4	−8.9 (4)	O3—C8—C9—C4	178.9 (2)
C1—N1—C3—C4	168.07 (19)	C7—C8—C9—C4	−0.9 (3)
O2—N2—C3—N1	176.8 (2)	C5—C4—C9—C8	1.6 (3)
C2—N2—C3—N1	−9.1 (2)	C3—C4—C9—C8	−176.9 (2)
O2—N2—C3—C4	−1.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cg2ⁱ	0.96	2.80	3.644 (2)	147

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₃N₂O₅
M_r	323.36
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	20.623 (3), 7.2168 (12), 22.831 (4)
V (Å³)	3398.0 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.25 × 0.17

Data collection
Diffractometer	Bruker SMART APEX2 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15858, 3027, 1519
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.119, 1.06
No. of reflections	3027
No. of parameters	216
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cg2ⁱ	0.96	2.80	3.644 (2)	147

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 20802092) for financial support.

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