Diethyl 4-acetyl-5-(2-nitro­phen­yl)pyrrolidine-2,2-dicarboxyl­ate

He, L.

doi:10.1107/S1600536810045691

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3205

https://doi.org/10.1107/S1600536810045691

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Diethyl 4-acetyl-5-(2-nitrophenyl)pyrrolidine-2,2-dicarboxylate

Long He ^a ^*

^aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: helongcwnu@yahoo.com.cn

(Received 30 October 2010; accepted 7 November 2010; online 17 November 2010)

The title compound, C₁₈H₂₂N₂O₇, was synthesized by the 1,3-dipolar cycloaddition reaction of but-3-en-2-one, diethyl 2-aminomalonate and 2-nitrobenzaldehyde. In the molecule, the pyrrolidine ring possesses an envelope conformation. Intermolecular N—H⋯O and C—H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For the biological activity of pyrrolidine derivatives, see: Coldham & Hufton (2005 ); Grigg (1995 ); Kravchenko et al. (2005 ); Nair & Suja (2007 ); Pandey et al. (2006 ); Sardina & Rapoport (1996 ); Witherup et al. (1995 ). For a related structure, see: He (2009 ).

Experimental

Crystal data

C₁₈H₂₂N₂O₇
M_r = 378.38
Monoclinic, P 2₁
a = 10.687 (5) Å
b = 7.760 (5) Å
c = 12.030 (5) Å
β = 97.455 (5)°
V = 989.2 (9) Å³
Z = 2
Cu Kα radiation
μ = 0.83 mm⁻¹
T = 291 K
0.38 × 0.36 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.743, T_max = 0.789
19238 measured reflections
2105 independent reflections
1915 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.166
S = 1.04
2105 reflections
249 parameters
42 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H10⋯O2ⁱ	0.92 (5)	2.51 (6)	3.244 (9)	138 (5)
C18—H18A⋯O4ⁱⁱ	0.96	2.53	3.460 (15)	162 (6)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+2]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045691/xu5078sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045691/xu5078Isup2.hkl

checkCIF report

Comment top

Substituted pyrrolidine compound is an important class of heterocyclic compounds with wide spread applications to the synthesis of biologically active compounds and natural products (Coldham et al., 2005; Grigg, 1995; Kravchenko et al., 2005; Nair et al., 2007; Pandey et al., 2006; Sardina et al., 1996; Witherup et al. 1995). Its crystal structure is reported here.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The pyrrolidine ring possesses an envelope conformation. The crystal packing is stabilized by N—H···0 and C—H···0 hydrogen bonding (Table 1).

Related literature top

For the biological activity of pyrrolidine derivatives, see: Coldham & Hufton (2005); Grigg (1995); Kravchenko et al. (2005); Nair & Suja (2007); Pandey et al. (2006); Sardina & Rapoport (1996); Witherup et al. (1995). For a related structure, see: He (2009).

Experimental top

2-Nitrobenzaldehyde (0.018 g, 0.12 mmol) and diethyl 2-aminomalonate (0.017 g, 0.1 mmol) were added to a solution of methyl but-3-en-2-one (0.014 g, 0.2 mmol) in dichloromethane (2 ml). To the stirred mixture, phosphenous acid (5 mg, 0.01 mmol) was added. After the mixture had been stirred at 293 K for 48 h, the reaction was quenched with a saturated solution of sodium bicarbonate (5 ml). The mixture was extracted with ethyl acetate, evaporated and separated by flash chromatograghy. A colourless powder was obtained. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution.

Structure description top

For the biological activity of pyrrolidine derivatives, see: Coldham & Hufton (2005); Grigg (1995); Kravchenko et al. (2005); Nair & Suja (2007); Pandey et al. (2006); Sardina & Rapoport (1996); Witherup et al. (1995). For a related structure, see: He (2009).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

Diethyl 4-acetyl-5-(2-nitrophenyl)pyrrolidine-2,2-dicarboxylate top

Crystal data top

C₁₈H₂₂N₂O₇	F(000) = 400
M_r = 378.38	D_x = 1.270 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 11509 reflections
a = 10.687 (5) Å	θ = 4.2–72.3°
b = 7.760 (5) Å	µ = 0.83 mm⁻¹
c = 12.030 (5) Å	T = 291 K
β = 97.455 (5)°	Block, colorless
V = 989.2 (9) Å³	0.38 × 0.36 × 0.30 mm
Z = 2

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2105 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1915 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
ω scans	θ_max = 72.6°, θ_min = 4.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −13→13
T_min = 0.743, T_max = 0.789	k = −8→9
19238 measured reflections	l = −14→14

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)] = 0.081	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.025P)² + 1.3702P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2105 reflections	Δρ_max = 0.33 e Å⁻³
249 parameters	Δρ_min = −0.42 e Å⁻³
42 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: 0.017 (3)

Crystal data top

C₁₈H₂₂N₂O₇	V = 989.2 (9) Å³
M_r = 378.38	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 10.687 (5) Å	µ = 0.83 mm⁻¹
b = 7.760 (5) Å	T = 291 K
c = 12.030 (5) Å	0.38 × 0.36 × 0.30 mm
β = 97.455 (5)°

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2105 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1915 reflections with I > 2σ(I)
T_min = 0.743, T_max = 0.789	R_int = 0.023
19238 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	42 restraints
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.33 e Å⁻³
2105 reflections	Δρ_min = −0.42 e Å⁻³
249 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
O3	0.0038 (5)	0.2421 (8)	0.5230 (4)	0.0881 (16)
N2	0.2698 (5)	0.3189 (8)	0.6658 (4)	0.0681 (15)
O5	0.1828 (5)	0.4223 (10)	0.8609 (6)	0.117 (2)
C3	0.2453 (6)	0.4941 (9)	0.4653 (6)	0.0641 (16)
H3	0.1941	0.5184	0.5202	0.077*
O1	0.4209 (6)	0.0223 (8)	0.4138 (5)	0.0957 (18)
C2	0.3126 (5)	0.3415 (9)	0.4718 (5)	0.0566 (14)
O6	0.4399 (5)	0.1838 (10)	0.8411 (4)	0.108 (2)
O4	0.0249 (5)	0.2457 (11)	0.8118 (5)	0.112 (2)
O2	0.5571 (5)	0.1618 (10)	0.3371 (5)	0.120 (2)
C8	0.1956 (6)	0.0846 (9)	0.5533 (5)	0.0631 (16)
H8	0.2247	−0.0192	0.5180	0.076*
N1	0.4602 (6)	0.1556 (10)	0.3797 (5)	0.0784 (17)
C7	0.3030 (5)	0.2205 (9)	0.5697 (4)	0.0589 (15)
H7	0.3841	0.1624	0.5905	0.071*
C1	0.3875 (5)	0.3157 (10)	0.3870 (5)	0.0605 (15)
C16	0.1311 (7)	0.2862 (12)	0.8096 (6)	0.079 (2)
C4	0.2514 (6)	0.6116 (10)	0.3802 (6)	0.0776 (19)
H4	0.2028	0.7113	0.3771	0.093*
C12	0.0663 (7)	0.1228 (11)	0.3583 (5)	0.085 (2)
H12A	−0.0097	0.1760	0.3228	0.128*
H12B	0.0620	0.0007	0.3455	0.128*
H12C	0.1375	0.1694	0.3274	0.128*
C11	0.0803 (6)	0.1578 (9)	0.4820 (5)	0.0649 (16)
O7	0.2881 (6)	0.0324 (11)	0.9076 (6)	0.130 (2)
C10	0.2269 (6)	0.1943 (11)	0.7453 (5)	0.0721 (19)
C6	0.3975 (6)	0.4353 (11)	0.3036 (6)	0.0732 (19)
H6	0.4511	0.4149	0.2500	0.088*
C13	0.3357 (7)	0.1387 (14)	0.8371 (6)	0.092 (2)
C9	0.1723 (8)	0.0442 (10)	0.6740 (5)	0.080 (2)
H9A	0.0826	0.0330	0.6782	0.096*
H9B	0.2137	−0.0625	0.6995	0.096*
C5	0.3294 (7)	0.5809 (11)	0.3001 (6)	0.084 (2)
H5	0.3350	0.6611	0.2435	0.101*
C17	0.1066 (10)	0.5318 (17)	0.9259 (8)	0.128 (3)
H17A	0.0174	0.5231	0.8985	0.154*
H17B	0.1325	0.6515	0.9246	0.154*
C14	0.3850 (10)	−0.0385 (18)	1.0007 (8)	0.137 (3)
H14A	0.3874	−0.1634	0.9994	0.165*
H14B	0.4687	0.0064	0.9954	0.165*
C15	0.3341 (11)	0.0277 (19)	1.1036 (8)	0.153 (3)
H15A	0.3856	−0.0141	1.1694	0.229*
H15B	0.2490	−0.0121	1.1036	0.229*
H15C	0.3352	0.1514	1.1034	0.229*
C18	0.1366 (11)	0.455 (2)	1.0415 (9)	0.158 (3)
H18A	0.0896	0.5141	1.0925	0.237*
H18B	0.2253	0.4664	1.0663	0.237*
H18C	0.1141	0.3350	1.0391	0.237*
H10	0.342 (4)	0.377 (8)	0.693 (5)	0.07 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.066 (2)	0.101 (4)	0.099 (4)	−0.003 (3)	0.016 (3)	−0.005 (3)
N2	0.073 (3)	0.076 (4)	0.056 (3)	−0.017 (3)	0.011 (2)	−0.010 (3)
O5	0.081 (3)	0.119 (5)	0.154 (4)	−0.015 (4)	0.020 (3)	−0.040 (5)
C3	0.059 (3)	0.062 (4)	0.073 (4)	−0.001 (3)	0.015 (3)	−0.002 (3)
O1	0.105 (4)	0.091 (4)	0.092 (4)	0.024 (4)	0.015 (3)	0.000 (4)
C2	0.048 (3)	0.065 (4)	0.057 (3)	−0.007 (3)	0.004 (2)	−0.003 (3)
O6	0.075 (3)	0.172 (7)	0.075 (3)	0.018 (4)	0.004 (2)	−0.009 (4)
O4	0.080 (3)	0.162 (7)	0.097 (4)	−0.018 (4)	0.025 (3)	0.000 (4)
O2	0.090 (3)	0.153 (6)	0.126 (4)	0.051 (4)	0.051 (3)	0.031 (5)
C8	0.072 (4)	0.058 (4)	0.059 (3)	−0.007 (3)	0.003 (3)	0.000 (3)
N1	0.076 (4)	0.093 (5)	0.067 (3)	0.020 (4)	0.011 (3)	−0.001 (4)
C7	0.058 (3)	0.066 (4)	0.051 (3)	−0.007 (3)	0.003 (2)	0.000 (3)
C1	0.053 (3)	0.070 (4)	0.058 (3)	0.005 (3)	0.007 (2)	0.000 (3)
C16	0.068 (4)	0.106 (7)	0.067 (4)	0.001 (5)	0.018 (3)	0.010 (4)
C4	0.076 (4)	0.066 (5)	0.091 (5)	0.002 (4)	0.014 (4)	0.005 (4)
C12	0.090 (5)	0.086 (6)	0.073 (4)	−0.010 (5)	−0.018 (3)	−0.001 (4)
C11	0.062 (3)	0.062 (4)	0.070 (4)	−0.014 (3)	0.006 (3)	−0.002 (3)
O7	0.124 (3)	0.135 (4)	0.131 (3)	−0.003 (3)	0.011 (2)	0.020 (3)
C10	0.071 (4)	0.092 (5)	0.053 (3)	−0.014 (4)	0.005 (3)	0.002 (4)
C6	0.072 (4)	0.084 (5)	0.065 (4)	0.002 (4)	0.019 (3)	0.001 (4)
C13	0.070 (4)	0.127 (7)	0.078 (4)	0.001 (4)	0.010 (3)	−0.023 (3)
C9	0.104 (5)	0.076 (5)	0.060 (4)	−0.021 (4)	0.008 (4)	0.006 (4)
C5	0.090 (5)	0.077 (5)	0.086 (5)	−0.005 (5)	0.018 (4)	0.015 (5)
C17	0.126 (4)	0.131 (4)	0.132 (3)	0.013 (3)	0.031 (3)	−0.018 (3)
C14	0.139 (4)	0.140 (4)	0.130 (3)	0.006 (3)	0.007 (2)	0.017 (3)
C15	0.165 (4)	0.155 (5)	0.134 (3)	0.009 (3)	0.004 (3)	−0.002 (3)
C18	0.168 (5)	0.165 (5)	0.142 (3)	0.009 (3)	0.026 (3)	−0.001 (3)

Geometric parameters (Å, º) top

O3—C11	1.202 (8)	C12—C11	1.501 (9)
N2—C7	1.467 (8)	C12—H12A	0.9600
N2—C10	1.474 (9)	C12—H12B	0.9600
N2—H10	0.92 (5)	C12—H12C	0.9600
O5—C16	1.308 (10)	O7—C13	1.330 (11)
O5—C17	1.470 (11)	O7—C14	1.525 (11)
C3—C4	1.378 (9)	C10—C9	1.518 (10)
C3—C2	1.383 (9)	C10—C13	1.557 (10)
C3—H3	0.9300	C6—C5	1.342 (11)
O1—N1	1.208 (9)	C6—H6	0.9300
C2—C1	1.390 (8)	C9—H9A	0.9700
C2—C7	1.521 (8)	C9—H9B	0.9700
O6—C13	1.162 (9)	C5—H5	0.9300
O4—C16	1.181 (8)	C17—C18	1.509 (9)
O2—N1	1.214 (7)	C17—H17A	0.9700
C8—C11	1.517 (8)	C17—H17B	0.9700
C8—C9	1.537 (8)	C14—C15	1.506 (9)
C8—C7	1.552 (8)	C14—H14A	0.9700
C8—H8	0.9800	C14—H14B	0.9700
N1—C1	1.474 (9)	C15—H15A	0.9600
C7—H7	0.9800	C15—H15B	0.9600
C1—C6	1.382 (9)	C15—H15C	0.9600
C16—C10	1.536 (10)	C18—H18A	0.9600
C4—C5	1.375 (9)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600

C7—N2—C10	107.3 (6)	N2—C10—C16	107.8 (6)
C7—N2—H10	105 (4)	C9—C10—C16	114.1 (6)
C10—N2—H10	114 (4)	N2—C10—C13	112.0 (6)
C16—O5—C17	119.2 (7)	C9—C10—C13	112.7 (7)
C4—C3—C2	122.3 (6)	C16—C10—C13	104.9 (5)
C4—C3—H3	118.9	C5—C6—C1	119.7 (6)
C2—C3—H3	118.9	C5—C6—H6	120.1
C3—C2—C1	115.3 (6)	C1—C6—H6	120.1
C3—C2—C7	119.1 (5)	O6—C13—O7	127.1 (9)
C1—C2—C7	125.6 (6)	O6—C13—C10	124.7 (9)
C11—C8—C9	113.0 (5)	O7—C13—C10	108.2 (7)
C11—C8—C7	110.5 (5)	C10—C9—C8	106.3 (6)
C9—C8—C7	103.1 (5)	C10—C9—H9A	110.5
C11—C8—H8	110.0	C8—C9—H9A	110.5
C9—C8—H8	110.0	C10—C9—H9B	110.5
C7—C8—H8	110.0	C8—C9—H9B	110.5
O1—N1—O2	122.1 (8)	H9A—C9—H9B	108.7
O1—N1—C1	119.4 (6)	C6—C5—C4	120.0 (7)
O2—N1—C1	118.5 (8)	C6—C5—H5	120.0
N2—C7—C2	109.7 (6)	C4—C5—H5	120.0
N2—C7—C8	101.8 (5)	O5—C17—C18	101.2 (9)
C2—C7—C8	116.4 (4)	O5—C17—H17A	111.5
N2—C7—H7	109.6	C18—C17—H17A	111.5
C2—C7—H7	109.6	O5—C17—H17B	111.5
C8—C7—H7	109.6	C18—C17—H17B	111.5
C6—C1—C2	122.8 (7)	H17A—C17—H17B	109.3
C6—C1—N1	115.6 (6)	C15—C14—O7	101.4 (8)
C2—C1—N1	121.6 (6)	C15—C14—H14A	111.5
O4—C16—O5	123.5 (8)	O7—C14—H14A	111.5
O4—C16—C10	126.3 (8)	C15—C14—H14B	111.5
O5—C16—C10	110.1 (6)	O7—C14—H14B	111.5
C5—C4—C3	119.8 (7)	H14A—C14—H14B	109.3
C5—C4—H4	120.1	C14—C15—H15A	109.5
C3—C4—H4	120.1	C14—C15—H15B	109.5
C11—C12—H12A	109.5	H15A—C15—H15B	109.5
C11—C12—H12B	109.5	C14—C15—H15C	109.5
H12A—C12—H12B	109.5	H15A—C15—H15C	109.5
C11—C12—H12C	109.5	H15B—C15—H15C	109.5
H12A—C12—H12C	109.5	C17—C18—H18A	109.5
H12B—C12—H12C	109.5	C17—C18—H18B	109.5
O3—C11—C12	121.3 (7)	H18A—C18—H18B	109.5
O3—C11—C8	121.1 (6)	C17—C18—H18C	109.5
C12—C11—C8	117.6 (6)	H18A—C18—H18C	109.5
C13—O7—C14	114.4 (7)	H18B—C18—H18C	109.5
N2—C10—C9	105.4 (5)

C4—C3—C2—C1	0.5 (9)	C7—N2—C10—C16	−150.7 (5)
C4—C3—C2—C7	178.7 (6)	C7—N2—C10—C13	94.5 (7)
C10—N2—C7—C2	164.3 (5)	O4—C16—C10—N2	120.5 (8)
C10—N2—C7—C8	40.5 (6)	O5—C16—C10—N2	−57.8 (8)
C3—C2—C7—N2	−25.6 (7)	O4—C16—C10—C9	3.7 (11)
C1—C2—C7—N2	152.3 (6)	O5—C16—C10—C9	−174.5 (7)
C3—C2—C7—C8	89.2 (7)	O4—C16—C10—C13	−120.0 (9)
C1—C2—C7—C8	−92.9 (7)	O5—C16—C10—C13	61.8 (9)
C11—C8—C7—N2	84.9 (6)	C2—C1—C6—C5	−2.4 (10)
C9—C8—C7—N2	−36.2 (6)	N1—C1—C6—C5	176.5 (7)
C11—C8—C7—C2	−34.3 (8)	C14—O7—C13—O6	−1.7 (14)
C9—C8—C7—C2	−155.3 (6)	C14—O7—C13—C10	178.0 (8)
C3—C2—C1—C6	1.7 (9)	N2—C10—C13—O6	−2.8 (12)
C7—C2—C1—C6	−176.3 (6)	C9—C10—C13—O6	115.9 (10)
C3—C2—C1—N1	−177.2 (6)	C16—C10—C13—O6	−119.5 (10)
C7—C2—C1—N1	4.8 (9)	N2—C10—C13—O7	177.5 (7)
O1—N1—C1—C6	−148.9 (7)	C9—C10—C13—O7	−63.8 (8)
O2—N1—C1—C6	29.6 (9)	C16—C10—C13—O7	60.8 (9)
O1—N1—C1—C2	30.0 (10)	N2—C10—C9—C8	4.1 (8)
O2—N1—C1—C2	−151.4 (6)	C16—C10—C9—C8	122.2 (6)
C17—O5—C16—O4	0.4 (13)	C13—C10—C9—C8	−118.4 (6)
C17—O5—C16—C10	178.7 (7)	C11—C8—C9—C10	−99.6 (7)
C2—C3—C4—C5	−2.0 (11)	C7—C8—C9—C10	19.7 (7)
C9—C8—C11—O3	30.1 (9)	C1—C6—C5—C4	0.8 (11)
C7—C8—C11—O3	−84.8 (8)	C3—C4—C5—C6	1.3 (11)
C9—C8—C11—C12	−150.7 (6)	C16—O5—C17—C18	93.1 (11)
C7—C8—C11—C12	94.4 (7)	C13—O7—C14—C15	119.5 (10)
C7—N2—C10—C9	−28.4 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H10···O2ⁱ	0.92 (5)	2.51 (6)	3.244 (9)	138 (5)
C18—H18A···O4ⁱⁱ	0.96	2.53	3.460 (15)	162 (6)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₂O₇
M_r	378.38
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	10.687 (5), 7.760 (5), 12.030 (5)
β (°)	97.455 (5)
V (Å³)	989.2 (9)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.38 × 0.36 × 0.30

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.743, 0.789
No. of measured, independent and observed [I > 2σ(I)] reflections	19238, 2105, 1915
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.166, 1.04
No. of reflections	2105
No. of parameters	249
No. of restraints	42
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.42

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H10···O2ⁱ	0.92 (5)	2.51 (6)	3.244 (9)	138 (5)
C18—H18A···O4ⁱⁱ	0.96	2.53	3.460 (15)	162 (6)

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

Acknowledgements

The diffraction measurements were made at the Centre for Testing and Analysis, Chengdu Branch, Chinese Academy of Sciences. I acknowledge financial support from China West Normal University.

References

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