4-[2-(3,4-Dimethoxy­phenethyl­amino)prop­oxy]-2-methoxy­benzamide

Wu, D.-Q.; Zhang, H.-B.; Xi, B.-M.

doi:10.1107/S1600536808015134

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1155

doi:10.1107/S1600536808015134

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4-[2-(3,4-Dimethoxyphenethylamino)propoxy]-2-methoxybenzamide

Dian-Qing Wu,^a,^b Hui-Bin Zhang ^b and Bao-Min Xi ^a ^*

^aDepartment of Medicinal Chemistry, College of Pharmacy, Southern Medical University, Guangzhou 510515, People's Republic of China, and ^bCenter of Drug Discovery, China Pharmaceutical University, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: xibaomin@yahoo.com.cn

(Received 12 May 2008; accepted 19 May 2008; online 24 May 2008)

The title compound, C₂₁H₂₈N₂O₅, has two intramolecular N—H⋯O hydrogen bonds. Intermolecular N—H⋯O hydrogen bonds [graph-set motif R₂²(8)] give rise to a dimer. Weak N—H⋯N hydrogen bonds between neighboring dimers further extend the crystal structure, which exhibits an infinite chain motif.

Related literature

For related literature, see: Allen et al. (1987 ); Beduschi & Beduachi (1998 ); Bernstein et al.(1995 ); Boonnak et al. (2005 ); Gunderman et al. (1995 ); Hieble et al. (1995 ); Kasztreiner et al. (1989 ); Ng et al. (2005 ); Xi et al. (2005 ).

Experimental

Crystal data

C₂₁H₂₈N₂O₅
M_r = 388.45
Monoclinic, P 2₁ /c
a = 7.7564 (3) Å
b = 9.3509 (4) Å
c = 29.9987 (12) Å
β = 95.370 (3)°
V = 2166.24 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 (2) K
0.21 × 0.18 × 0.17 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: none
26019 measured reflections
3909 independent reflections
1966 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.183
S = 1.03
3909 reflections
260 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 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
N2—H2A⋯O5ⁱ	0.86	2.05	2.909 (3)	178
N2—H2B⋯O4	0.86	2.04	2.684 (3)	131
N2—H2B⋯N1ⁱⁱ	0.86	2.54	3.161 (3)	129
N1—H1⋯O1	0.903 (17)	2.41 (3)	2.798 (3)	106 (2)
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015134/zl2117sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015134/zl2117Isup2.hkl

checkCIF report

Comment top

α1-Adrenoreceptors (α1-AR) are members of the super family of seven transmembrane G protein coupled receptors (GPCR) (Gunderman et al., 1995) and regulate several important physiological processes (Hieble et al., 1995). In recent years, the search for new α1-adrenoreceptor antagonists has increased in parallel with the development of postsynaptically selective α-adrenoreceptor antagonists due to their importance in the treatment of hypertension (Kasztreiner et al., 1989) and for prostatic hypertrophy (Beduschi & Beduachi, 1998). In the course of our studies on phenoxylalkylamine-phenylethanamine derivatives as potential antagonists of α1-adrenoreceptors, we have synthesized a library of compounds (Xi et al. , 2005) that show good activity. The title compound is one such phenoxylalkylamine-phenylethanamine derivative with α1-adrenoreceptor antagonist properties.

In the title compound (Fig. 1), the C—C bond lengths show normal values (Allen et al., 1987), and the C—O and C=O bond lengths are comparable to those observed in simliar structures (Ng et al., 2005; Boonnak et al., 2005), while the C—N distances in the structure fall in the range of 1.308 (3)–1.469 (4) Å. The title molecular structure acts as hydrogen bonding donor and acceptor with two intramolecular N—H···O hydrogen bonds. The compound forms dimers with neighboring molecules through N—H···O hydrogen bonding with a R₂²(8) graph set motif (Bernstein et al., 1995), which are further self-assembled by N—H···N hydrogen bonds (table 1) to form an infinite chain (Fig. 2).

Related literature top

For related literature, see: Allen et al. (1987); Beduschi & Beduachi (1998); Bernstein et al.(1995); Boonnak et al. (2005); Gunderman et al. (1995); Hieble et al. (1995); Kasztreiner et al. (1989); Ng et al. (2005); Xi et al. (2005).

Experimental top

A mixture of 2-methoxy-4-(2-oxopropoxy)benzamide (0.4 g), 2-(3,4-dimethoxy- phenyl)ethanamine (0.4 ml), TsOH (3 drops), and methanol (20 ml) were heated to reflux of the solvent for 3 h. After cooling KBH₄ (0.2 g) was added to the mixture portion wise over a period of 1 h and the mixture was stirred at room temperature for another 2 h. The methanol was evaporated, and water (15 ml) was added to the residue. The aqueous solution was extracted with ethyl acetate and the extract was dried over MgSO₄, and evaporated. The residue was chromatographed on silica gel with petroleum ether and ethyl acetate (1:2 with triethylamine) as the eluent to obtain the colorless block crystals (0.3 g, 69.6%).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure showing the atomic-numbering scheme. Displacement ellipsoids drawn at the 30% probability level. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. The molecular packing showing the intermolecular hydrogen bonding interactions as broken lines.

4-[2-(3,4-Dimethoxyphenethylamino)propoxy]-2-methoxybenzamide top

Crystal data top

C₂₁H₂₈N₂O₅	F(000) = 832
M_r = 388.45	D_x = 1.191 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2279 reflections
a = 7.7564 (3) Å	θ = 2.3–28.0°
b = 9.3509 (4) Å	µ = 0.09 mm⁻¹
c = 29.9987 (12) Å	T = 296 K
β = 95.370 (3)°	Block, colorless
V = 2166.24 (15) Å³	0.21 × 0.18 × 0.17 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	1966 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.069
Graphite monochromator	θ_max = 25.2°, θ_min = 2.3°
ϕ and ω scans	h = −8→9
26019 measured reflections	k = −11→11
3909 independent reflections	l = −35→35

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0802P)² + 0.288P] where P = (F_o² + 2F_c²)/3
3909 reflections	(Δ/σ)_max < 0.001
260 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₂₈N₂O₅	V = 2166.24 (15) Å³
M_r = 388.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7564 (3) Å	µ = 0.09 mm⁻¹
b = 9.3509 (4) Å	T = 296 K
c = 29.9987 (12) Å	0.21 × 0.18 × 0.17 mm
β = 95.370 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	1966 reflections with I > 2σ(I)
26019 measured reflections	R_int = 0.069
3909 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	1 restraint
wR(F²) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.24 e Å⁻³
3909 reflections	Δρ_min = −0.22 e Å⁻³
260 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	1.0849 (4)	0.9275 (3)	0.68939 (10)	0.0707 (8)
C2	1.0775 (4)	0.8967 (3)	0.73403 (10)	0.0730 (9)
H2	1.0012	0.8264	0.7419	0.088*
C3	1.1788 (4)	0.9662 (3)	0.76742 (11)	0.0768 (9)
C4	1.2923 (4)	1.0728 (3)	0.75616 (13)	0.0802 (9)
C5	1.3002 (4)	1.1052 (4)	0.71190 (14)	0.0894 (10)
H5	1.3752	1.1762	0.7038	0.107*
C6	1.1968 (5)	1.0324 (4)	0.67897 (12)	0.0854 (10)
H6	1.2040	1.0558	0.6491	0.102*
C7	0.2048 (4)	0.3654 (3)	0.58051 (10)	0.0731 (9)
H7	0.1768	0.2941	0.6002	0.088*
C8	0.2697 (4)	0.4909 (4)	0.59783 (10)	0.0786 (9)
H8	0.2876	0.5034	0.6287	0.094*
C9	0.3086 (4)	0.5986 (3)	0.56951 (10)	0.0652 (8)
C10	0.2844 (3)	0.5786 (3)	0.52359 (9)	0.0637 (8)
H10	0.3093	0.6521	0.5043	0.076*
C11	0.2230 (3)	0.4489 (3)	0.50650 (9)	0.0571 (7)
C12	0.1785 (3)	0.3388 (3)	0.53488 (9)	0.0604 (7)
C13	1.0809 (9)	0.8210 (6)	0.82400 (14)	0.194 (3)
H13A	0.9600	0.8442	0.8191	0.292*
H13B	1.1095	0.7984	0.8550	0.292*
H13C	1.1054	0.7400	0.8059	0.292*
C14	0.4230 (4)	0.8365 (3)	0.56233 (10)	0.0785 (9)
H14A	0.3207	0.8859	0.5491	0.094*
H14B	0.4874	0.8014	0.5384	0.094*
C15	0.5335 (4)	0.9363 (3)	0.59209 (10)	0.0752 (9)
H15	0.4726	0.9616	0.6182	0.090*
C16	0.8086 (4)	0.9358 (3)	0.63960 (10)	0.0766 (9)
H16A	0.7475	0.9578	0.6655	0.092*
H16B	0.8422	1.0254	0.6266	0.092*
C17	0.9687 (4)	0.8500 (4)	0.65416 (10)	0.0833 (10)
H17A	1.0321	0.8313	0.6284	0.100*
H17B	0.9348	0.7588	0.6660	0.100*
C18	1.5228 (7)	1.2293 (6)	0.78212 (16)	0.171 (2)
H18A	1.5999	1.1812	0.7638	0.257*
H18B	1.5858	1.2594	0.8096	0.257*
H18C	1.4738	1.3113	0.7664	0.257*
C19	0.5701 (5)	1.0702 (3)	0.56651 (13)	0.1053 (12)
H19A	0.6320	1.1371	0.5863	0.158*
H19B	0.4628	1.1121	0.5544	0.158*
H19C	0.6388	1.0465	0.5425	0.158*
C20	0.2483 (4)	0.5301 (3)	0.43139 (9)	0.0771 (9)
H20A	0.1776	0.6133	0.4343	0.116*
H20B	0.2303	0.4945	0.4013	0.116*
H20C	0.3679	0.5551	0.4381	0.116*
C21	0.1018 (4)	0.1977 (3)	0.52065 (11)	0.0676 (8)
N1	0.6938 (3)	0.8582 (2)	0.60697 (8)	0.0666 (7)
H1	0.662 (4)	0.780 (2)	0.6217 (8)	0.080*
N2	0.0991 (3)	0.1560 (3)	0.47879 (8)	0.0817 (8)
H2A	0.0548	0.0747	0.4708	0.098*
H2B	0.1417	0.2102	0.4594	0.098*
O1	0.3744 (3)	0.7205 (2)	0.58938 (6)	0.0838 (7)
O2	1.1798 (4)	0.9383 (3)	0.81226 (8)	0.1191 (10)
O3	1.3892 (3)	1.1353 (3)	0.79165 (9)	0.1160 (9)
O4	0.2023 (3)	0.4228 (2)	0.46171 (6)	0.0753 (6)
O5	0.0413 (4)	0.1217 (2)	0.54918 (8)	0.1049 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.063 (2)	0.075 (2)	0.073 (2)	0.0073 (17)	0.0014 (16)	0.0039 (17)
C2	0.065 (2)	0.071 (2)	0.082 (2)	−0.0139 (16)	0.0032 (16)	−0.0044 (17)
C3	0.079 (2)	0.076 (2)	0.076 (2)	−0.0129 (19)	0.0067 (18)	−0.0039 (17)
C4	0.072 (2)	0.070 (2)	0.099 (3)	−0.0126 (18)	0.0079 (19)	−0.011 (2)
C5	0.073 (2)	0.077 (2)	0.120 (3)	−0.0097 (19)	0.019 (2)	0.015 (2)
C6	0.081 (2)	0.090 (3)	0.086 (2)	0.011 (2)	0.012 (2)	0.018 (2)
C7	0.082 (2)	0.070 (2)	0.069 (2)	−0.0096 (18)	0.0146 (16)	0.0086 (16)
C8	0.091 (2)	0.083 (2)	0.0625 (18)	−0.0174 (19)	0.0095 (17)	0.0007 (18)
C9	0.0610 (19)	0.0651 (19)	0.069 (2)	−0.0088 (15)	0.0022 (15)	−0.0018 (16)
C10	0.0598 (19)	0.0609 (18)	0.069 (2)	−0.0022 (15)	−0.0005 (14)	0.0091 (15)
C11	0.0533 (17)	0.0567 (17)	0.0608 (18)	0.0012 (14)	0.0018 (13)	0.0001 (14)
C12	0.0518 (17)	0.0616 (18)	0.0688 (19)	−0.0031 (14)	0.0103 (14)	0.0015 (15)
C13	0.327 (8)	0.172 (5)	0.088 (3)	−0.131 (6)	0.039 (4)	−0.003 (3)
C14	0.081 (2)	0.066 (2)	0.085 (2)	−0.0101 (17)	−0.0076 (17)	0.0068 (17)
C15	0.069 (2)	0.0654 (19)	0.088 (2)	−0.0055 (17)	−0.0093 (17)	0.0026 (17)
C16	0.074 (2)	0.075 (2)	0.079 (2)	−0.0001 (17)	−0.0057 (17)	−0.0088 (16)
C17	0.083 (2)	0.087 (2)	0.077 (2)	0.0133 (19)	−0.0053 (18)	−0.0072 (17)
C18	0.145 (4)	0.178 (5)	0.192 (5)	−0.105 (4)	0.023 (4)	−0.035 (4)
C19	0.101 (3)	0.071 (2)	0.137 (3)	−0.008 (2)	−0.022 (2)	0.009 (2)
C20	0.089 (2)	0.073 (2)	0.0697 (19)	0.0018 (18)	0.0097 (17)	0.0126 (16)
C21	0.067 (2)	0.0626 (19)	0.074 (2)	−0.0052 (16)	0.0160 (16)	0.0004 (17)
N1	0.0687 (17)	0.0610 (15)	0.0689 (15)	−0.0033 (13)	0.0005 (13)	−0.0027 (12)
N2	0.101 (2)	0.0681 (16)	0.0786 (18)	−0.0248 (15)	0.0219 (15)	−0.0060 (14)
O1	0.0948 (17)	0.0803 (15)	0.0759 (14)	−0.0244 (13)	0.0059 (12)	−0.0059 (12)
O2	0.157 (2)	0.126 (2)	0.0737 (16)	−0.0677 (19)	0.0075 (15)	−0.0092 (14)
O3	0.1067 (19)	0.113 (2)	0.128 (2)	−0.0478 (17)	0.0056 (16)	−0.0250 (16)
O4	0.0972 (16)	0.0654 (13)	0.0627 (13)	−0.0120 (11)	0.0038 (11)	0.0065 (10)
O5	0.147 (2)	0.0836 (16)	0.0905 (16)	−0.0453 (16)	0.0465 (15)	−0.0088 (13)

Geometric parameters (Å, º) top

C1—C6	1.365 (4)	C14—C15	1.503 (4)
C1—C2	1.376 (4)	C14—H14A	0.9700
C1—C17	1.509 (4)	C14—H14B	0.9700
C2—C3	1.377 (4)	C15—N1	1.475 (4)
C2—H2	0.9300	C15—C19	1.509 (4)
C3—O2	1.369 (4)	C15—H15	0.9800
C3—C4	1.393 (4)	C16—N1	1.454 (3)
C4—C5	1.369 (4)	C16—C17	1.508 (4)
C4—O3	1.375 (4)	C16—H16A	0.9700
C5—C6	1.391 (5)	C16—H16B	0.9700
C5—H5	0.9300	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C7—C8	1.361 (4)	C18—O3	1.408 (4)
C7—C12	1.387 (4)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.369 (4)	C18—H18C	0.9600
C8—H8	0.9300	C19—H19A	0.9600
C9—O1	1.363 (3)	C19—H19B	0.9600
C9—C10	1.385 (4)	C19—H19C	0.9600
C10—C11	1.383 (4)	C20—O4	1.422 (3)
C10—H10	0.9300	C20—H20A	0.9600
C11—O4	1.360 (3)	C20—H20B	0.9600
C11—C12	1.400 (4)	C20—H20C	0.9600
C12—C21	1.493 (4)	C21—O5	1.238 (3)
C13—O2	1.403 (5)	C21—N2	1.313 (3)
C13—H13A	0.9600	N1—H1	0.903 (17)
C13—H13B	0.9600	N2—H2A	0.8600
C13—H13C	0.9600	N2—H2B	0.8600
C14—O1	1.426 (3)

C6—C1—C2	117.3 (3)	N1—C15—C19	111.8 (3)
C6—C1—C17	122.4 (3)	C14—C15—C19	109.7 (3)
C2—C1—C17	120.3 (3)	N1—C15—H15	109.5
C1—C2—C3	122.4 (3)	C14—C15—H15	109.5
C1—C2—H2	118.8	C19—C15—H15	109.5
C3—C2—H2	118.8	N1—C16—C17	111.4 (2)
O2—C3—C2	125.1 (3)	N1—C16—H16A	109.3
O2—C3—C4	115.4 (3)	C17—C16—H16A	109.3
C2—C3—C4	119.5 (3)	N1—C16—H16B	109.3
C5—C4—O3	125.9 (3)	C17—C16—H16B	109.3
C5—C4—C3	118.7 (3)	H16A—C16—H16B	108.0
O3—C4—C3	115.4 (3)	C16—C17—C1	111.6 (3)
C4—C5—C6	120.4 (3)	C16—C17—H17A	109.3
C4—C5—H5	119.8	C1—C17—H17A	109.3
C6—C5—H5	119.8	C16—C17—H17B	109.3
C1—C6—C5	121.7 (3)	C1—C17—H17B	109.3
C1—C6—H6	119.1	H17A—C17—H17B	108.0
C5—C6—H6	119.1	O3—C18—H18A	109.5
C8—C7—C12	123.2 (3)	O3—C18—H18B	109.5
C8—C7—H7	118.4	H18A—C18—H18B	109.5
C12—C7—H7	118.4	O3—C18—H18C	109.5
C7—C8—C9	119.5 (3)	H18A—C18—H18C	109.5
C7—C8—H8	120.3	H18B—C18—H18C	109.5
C9—C8—H8	120.3	C15—C19—H19A	109.5
O1—C9—C8	116.0 (3)	C15—C19—H19B	109.5
O1—C9—C10	123.9 (3)	H19A—C19—H19B	109.5
C8—C9—C10	120.0 (3)	C15—C19—H19C	109.5
C11—C10—C9	119.8 (3)	H19A—C19—H19C	109.5
C11—C10—H10	120.1	H19B—C19—H19C	109.5
C9—C10—H10	120.1	O4—C20—H20A	109.5
O4—C11—C10	121.9 (2)	O4—C20—H20B	109.5
O4—C11—C12	117.1 (2)	H20A—C20—H20B	109.5
C10—C11—C12	121.0 (3)	O4—C20—H20C	109.5
C7—C12—C11	116.5 (3)	H20A—C20—H20C	109.5
C7—C12—C21	117.3 (3)	H20B—C20—H20C	109.5
C11—C12—C21	126.2 (3)	O5—C21—N2	121.2 (3)
O2—C13—H13A	109.5	O5—C21—C12	118.4 (3)
O2—C13—H13B	109.5	N2—C21—C12	120.4 (3)
H13A—C13—H13B	109.5	C16—N1—C15	113.7 (2)
O2—C13—H13C	109.5	C16—N1—H1	104.8 (18)
H13A—C13—H13C	109.5	C15—N1—H1	106.9 (19)
H13B—C13—H13C	109.5	C21—N2—H2A	120.0
O1—C14—C15	107.5 (2)	C21—N2—H2B	120.0
O1—C14—H14A	110.2	H2A—N2—H2B	120.0
C15—C14—H14A	110.2	C9—O1—C14	119.7 (2)
O1—C14—H14B	110.2	C3—O2—C13	116.3 (3)
C15—C14—H14B	110.2	C4—O3—C18	117.9 (3)
H14A—C14—H14B	108.5	C11—O4—C20	119.4 (2)
N1—C15—C14	106.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.86	2.05	2.909 (3)	178
N2—H2B···O4	0.86	2.04	2.684 (3)	131
N2—H2B···N1ⁱⁱ	0.86	2.54	3.161 (3)	129
N1—H1···O1	0.90 (2)	2.41 (3)	2.798 (3)	106 (2)

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₈N₂O₅
M_r	388.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.7564 (3), 9.3509 (4), 29.9987 (12)
β (°)	95.370 (3)
V (Å³)	2166.24 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.21 × 0.18 × 0.17

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26019, 3909, 1966
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.183, 1.03
No. of reflections	3909
No. of parameters	260
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.86	2.05	2.909 (3)	177.7
N2—H2B···O4	0.86	2.04	2.684 (3)	130.6
N2—H2B···N1ⁱⁱ	0.86	2.54	3.161 (3)	129.3
N1—H1···O1	0.903 (17)	2.41 (3)	2.798 (3)	106 (2)

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

Acknowledgements

The authors acknowledge the National Natural Science Foundation of China for funding (grant No. 30600776).

References

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