(2S*,3R*,4S*,5R*)-3-(S*-1-Benzyl­oxy­ethyl)-4-methyl-4-nitro-5-phenyl­proline methyl ester

Linden, A.; Ayerbe, M.; Arrieta, A.; Zubia, A.; Vivanco, S.; Erquicia, E.; Aldaba, E.; Cossío, F.P.; Lecea, B.

doi:10.1107/S1600536801018104

(2S,3R,4S,5R)-3-(S*-1-Benzyloxyethyl)-4-methyl-4-nitro-5-phenylproline methyl ester

A. Linden, M. Ayerbe, A. Arrieta, A. Zubia, S. Vivanco, E. Erquicia, E. Aldaba, F. P. Cossío and B. Lecea

At 173 K, the five-membered ring of the title compound, C₂₂H₂₆N₂O₅, has an envelope conformation. The amine group is involved in both intramolecular and intermolecular hydrogen bonds, the latter linking the molecules into centrosymmetric dimers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018104/cf6119sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018104/cf6119Isup2.hkl Contains datablock I

CCDC reference: 176043

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Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.049
wR factor = 0.142
Data-to-parameter ratio = 17.5

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No syntax errors found

ADDSYM reports no extra symmetry

Comment top

The title compound, (3c), is one of three diastereoisomeric products, (3a-c), obtained from the [3 + 2]-cycloaddition of the chiral nitroalkene (1) with the silver azomethine ylide derived from imine (2) (Ayerbe et al., 1998). Diastereoisomer (3a) could not be isolated; its absolute configuration was assumed by analogy with the compounds obtained in our previous work (Ayerbe et al., 1998). Compound (3 b) did not give crystals that were suitable for X-ray diffraction. Its relative configuration was determined by NOE experiments. The minor diastereoisomer (3c) was successfully crystallized from ethanol and fully characterized.

The puckering parameters (Cremer & Pople, 1975) for the five-membered ring are: q₂ = 0.463 (2) Å and ϕ₂ = 321.4 (2)°. The latter parameter is close to a value (324°) that is appropriate for an envelope conformation. The envelope flap is formed by C5, which lies 0.699 (3) Å from the plane defined by atoms N1, C2, C3 and C4. This puckering causes significant contraction of the N1—C5—C4 angle (Table 1).

The amine group of the molecule forms long, weak bifurcated hydrogen bonds with the carbonyl O atom of the ester substituent (Table 2). One interaction is intramolecular and completes a closed five-membered loop with a graph set motif of S(5) (Bernstein et al., 1995). The second is an intermolecular interaction with a neighbouring molecule, which is related to the original molecule by a centre of inversion. The intermolecular interactions thus link the molecules into hydrogen-bonded dimers which have a graph set motif of R²₂(10).

Experimental top

The title compound was prepared according to the procedure of Ayerbe et al. (1998). The reaction gave a mixture of three diastereoismers, (3a–c), in the proportions 59:29:12, which were separated by flash chromatography (ethyl acetate/hexane, 1:10). Suitable crystals were obtained by evaporation of an ethanol solution (m.p. 454–455 K). Spectroscopic analysis: IR (KBr, ν cm^-1): 3328, 1722, 1535, 1381; ¹H NMR (CDCl₃, δ, p.p.m.): 7.31–7.14 (m, 10H), 4.96 (s_b, 1H), 4.59 (d, 1H, J = 11.5 Hz), 4.33 (d, 1H, J = 11.5 Hz), 3.81 (s, 3H), 3.71 (m, 3H), 2.52 (s, 1H), 1.30 (d, 3H, J = 5.3 Hz), 1.26 (s, 3H); ¹³C NMR (CDCl₃, δ, p.p.m.): 174.8, 137.6, 135.7, 128.6, 128.3, 128.2, 127.6, 127.5, 127.1, 112.3, 94.6, 73.7, 70.6, 70.1, 58.3, 57.0, 52.7, 17.0, 13.7; analysis, calculated for C₂₂H₂₆N₂O₅: C 66.30, H 6.59, N 7.03%; found: C 65.99, H 6.56, N 7.08%.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2001).

Figures top

	Fig. 1. View of the molecule of (3c) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
	Fig. 2. The molecular packing of (3c) viewed along the b axis. H atoms bonded to C atoms have been omitted for clarity. Red lines indicate the hydrogen bonding interactions.

(2S*, 3R*, 4S*, 5R*)-3-(S*-1-benzyloxyethyl)-4-methyl-4-nitro-5- phenylproline methyl ester top

Crystal data top

C₂₂H₂₆N₂O₅	F(000) = 848
M_r = 398.45	D_x = 1.283 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 454 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.245 (2) Å	Cell parameters from 25 reflections
b = 8.4082 (17) Å	θ = 17.0–19.5°
c = 26.6330 (15) Å	µ = 0.09 mm⁻¹
β = 94.802 (11)°	T = 173 K
V = 2063.1 (6) Å³	Prism, colourless
Z = 4	0.50 × 0.32 × 0.22 mm

Data collection top

Rigaku AFC-5R diffractometer	R_int = 0.020
Radiation source: Rigaku rotating anode generator	θ_max = 27.5°, θ_min = 2.5°
Graphite monochromator	h = 0→12
ω scans	k = 0→10
5348 measured reflections	l = −34→34
4719 independent reflections	3 standard reflections every 150 reflections
2920 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0528P)² + 0.4415P] where P = (F_o² + 2F_c²)/3
4719 reflections	(Δ/σ)_max = 0.001
269 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₂₆N₂O₅	V = 2063.1 (6) Å³
M_r = 398.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.245 (2) Å	µ = 0.09 mm⁻¹
b = 8.4082 (17) Å	T = 173 K
c = 26.6330 (15) Å	0.50 × 0.32 × 0.22 mm
β = 94.802 (11)°

Data collection top

Rigaku AFC-5R diffractometer	R_int = 0.020
5348 measured reflections	3 standard reflections every 150 reflections
4719 independent reflections	intensity decay: none
2920 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.27 e Å⁻³
4719 reflections	Δρ_min = −0.19 e Å⁻³
269 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.4580 (0.0094) x - 2.4899 (0.0095) y + 22.4909 (0.0142) z = 3.6175 (0.0115)

* 0.0073 (0.0011) C2 * -0.0069 (0.0011) C3 * 0.0047 (0.0007) C4 * -0.0050 (0.0008) N1 - 0.6987 (0.0027) C5

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
O1	0.61730 (17)	0.9198 (2)	0.07951 (7)	0.0597 (5)
O2	0.7218 (2)	1.0383 (2)	0.14481 (7)	0.0721 (5)
O6	0.80889 (18)	0.4743 (2)	0.00001 (5)	0.0576 (5)
O7	0.65473 (18)	0.3568 (2)	0.04833 (5)	0.0572 (4)
O10	0.59975 (15)	0.68719 (16)	0.18720 (4)	0.0383 (3)
N1	0.95987 (18)	0.6213 (2)	0.08183 (6)	0.0397 (4)
H1	1.008 (2)	0.591 (3)	0.0549 (9)	0.053 (7)*
N2	0.7077 (2)	0.9252 (2)	0.11587 (7)	0.0472 (5)
C2	0.8363 (2)	0.5196 (2)	0.09011 (7)	0.0378 (5)
H2	0.8698	0.4299	0.1129	0.045*
C3	0.7304 (2)	0.6274 (2)	0.11770 (7)	0.0345 (4)
H3	0.6410	0.6444	0.0945	0.041*
C4	0.8129 (2)	0.7876 (2)	0.12326 (7)	0.0368 (4)
C5	0.9054 (2)	0.7839 (2)	0.07735 (7)	0.0357 (4)
H5	0.8390	0.7926	0.0458	0.043*
C6	0.7655 (2)	0.4513 (2)	0.04074 (7)	0.0393 (5)
C8	0.5836 (3)	0.2781 (3)	0.00460 (9)	0.0622 (7)
H81	0.5491	0.3579	−0.0204	0.093*
H82	0.5011	0.2162	0.0147	0.093*
H83	0.6527	0.2069	−0.0101	0.093*
C9	0.6837 (2)	0.5613 (2)	0.16744 (7)	0.0418 (5)
H9	0.7717	0.5408	0.1910	0.050*
C11	0.5888 (3)	0.6765 (3)	0.24016 (7)	0.0466 (5)
H111	0.6864	0.6868	0.2582	0.056*
H112	0.5487	0.5714	0.2485	0.056*
C12	0.4914 (2)	0.8065 (2)	0.25670 (7)	0.0372 (4)
C13	0.4452 (3)	0.9301 (3)	0.22514 (8)	0.0530 (6)
H13	0.4788	0.9370	0.1925	0.064*
C14	0.3502 (3)	1.0442 (3)	0.24071 (9)	0.0617 (7)
H14	0.3189	1.1284	0.2186	0.074*
C15	0.3009 (3)	1.0360 (3)	0.28824 (9)	0.0529 (6)
H15	0.2344	1.1129	0.2986	0.063*
C16	0.3491 (2)	0.9151 (3)	0.32042 (8)	0.0456 (5)
H16	0.3176	0.9101	0.3534	0.055*
C17	0.4431 (2)	0.8014 (2)	0.30466 (7)	0.0390 (5)
H17	0.4753	0.7183	0.3270	0.047*
C18	0.5942 (3)	0.4103 (3)	0.16107 (9)	0.0620 (7)
H181	0.5632	0.3776	0.1938	0.093*
H182	0.6529	0.3258	0.1476	0.093*
H183	0.5086	0.4301	0.1376	0.093*
C19	0.9070 (2)	0.8094 (3)	0.17272 (7)	0.0505 (6)
H191	0.9637	0.9075	0.1712	0.076*
H192	0.9729	0.7185	0.1780	0.076*
H193	0.8447	0.8160	0.2007	0.076*
C20	1.0205 (2)	0.9107 (3)	0.07653 (7)	0.0389 (5)
C21	1.1639 (2)	0.8830 (3)	0.09425 (8)	0.0527 (6)
H21	1.1927	0.7816	0.1073	0.063*
C22	1.2667 (3)	1.0073 (4)	0.09275 (9)	0.0648 (8)
H22	1.3649	0.9891	0.1048	0.078*
C23	1.2256 (3)	1.1538 (4)	0.07398 (9)	0.0617 (7)
H23	1.2957	1.2361	0.0730	0.074*
C24	1.0837 (3)	1.1827 (3)	0.05655 (9)	0.0564 (6)
H24	1.0554	1.2848	0.0440	0.068*
C25	0.9824 (2)	1.0613 (3)	0.05753 (8)	0.0453 (5)
H25	0.8848	1.0809	0.0450	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0434 (9)	0.0550 (10)	0.0800 (12)	0.0131 (8)	0.0009 (8)	0.0142 (9)
O2	0.1003 (14)	0.0404 (9)	0.0794 (12)	0.0098 (9)	0.0309 (11)	−0.0150 (9)
O6	0.0690 (11)	0.0699 (11)	0.0353 (8)	−0.0160 (9)	0.0124 (7)	−0.0108 (7)
O7	0.0670 (10)	0.0668 (11)	0.0397 (8)	−0.0202 (9)	0.0149 (7)	−0.0151 (8)
O10	0.0506 (8)	0.0380 (8)	0.0277 (6)	0.0101 (6)	0.0112 (6)	0.0010 (6)
N1	0.0416 (9)	0.0425 (10)	0.0359 (9)	0.0082 (8)	0.0091 (7)	−0.0085 (8)
N2	0.0476 (11)	0.0389 (10)	0.0577 (12)	0.0060 (9)	0.0201 (9)	−0.0013 (9)
C2	0.0453 (12)	0.0386 (11)	0.0301 (10)	0.0079 (9)	0.0061 (8)	−0.0043 (8)
C3	0.0423 (11)	0.0327 (10)	0.0289 (9)	0.0062 (9)	0.0062 (8)	−0.0031 (8)
C4	0.0388 (10)	0.0378 (11)	0.0345 (10)	0.0060 (9)	0.0077 (8)	−0.0065 (8)
C5	0.0337 (10)	0.0422 (11)	0.0314 (9)	0.0046 (9)	0.0035 (8)	−0.0049 (8)
C6	0.0461 (11)	0.0378 (11)	0.0349 (10)	0.0063 (9)	0.0084 (9)	−0.0064 (8)
C8	0.0658 (16)	0.0678 (17)	0.0539 (14)	−0.0180 (14)	0.0102 (12)	−0.0206 (13)
C9	0.0551 (12)	0.0379 (11)	0.0337 (10)	0.0132 (10)	0.0112 (9)	−0.0006 (8)
C11	0.0606 (13)	0.0521 (13)	0.0283 (10)	0.0170 (11)	0.0103 (9)	0.0044 (9)
C12	0.0408 (11)	0.0388 (11)	0.0325 (9)	0.0050 (9)	0.0060 (8)	−0.0007 (8)
C13	0.0650 (15)	0.0590 (14)	0.0369 (11)	0.0220 (12)	0.0158 (10)	0.0091 (10)
C14	0.0743 (17)	0.0571 (15)	0.0544 (14)	0.0285 (13)	0.0087 (12)	0.0093 (12)
C15	0.0532 (13)	0.0499 (14)	0.0564 (14)	0.0149 (11)	0.0098 (11)	−0.0116 (11)
C16	0.0480 (12)	0.0511 (13)	0.0394 (11)	0.0000 (11)	0.0142 (9)	−0.0089 (10)
C17	0.0450 (11)	0.0402 (11)	0.0323 (9)	−0.0001 (9)	0.0062 (8)	−0.0018 (9)
C18	0.097 (2)	0.0396 (13)	0.0540 (14)	−0.0008 (13)	0.0354 (14)	−0.0007 (11)
C19	0.0539 (13)	0.0635 (15)	0.0344 (10)	0.0000 (12)	0.0067 (9)	−0.0123 (10)
C20	0.0368 (10)	0.0506 (13)	0.0303 (9)	−0.0016 (9)	0.0082 (8)	−0.0114 (9)
C21	0.0392 (12)	0.0730 (16)	0.0462 (12)	0.0030 (12)	0.0061 (9)	−0.0090 (12)
C22	0.0342 (12)	0.109 (2)	0.0514 (14)	−0.0076 (14)	0.0067 (10)	−0.0191 (15)
C23	0.0632 (16)	0.0756 (19)	0.0500 (14)	−0.0236 (14)	0.0257 (12)	−0.0221 (13)
C24	0.0644 (16)	0.0588 (15)	0.0490 (13)	−0.0124 (13)	0.0236 (11)	−0.0137 (11)
C25	0.0472 (12)	0.0476 (13)	0.0423 (11)	−0.0032 (10)	0.0108 (9)	−0.0063 (10)

Geometric parameters (Å, º) top

O1—N2	1.226 (2)	C12—C13	1.382 (3)
O2—N2	1.225 (2)	C12—C17	1.388 (3)
O6—C6	1.203 (2)	C13—C14	1.387 (3)
O7—C6	1.325 (3)	C13—H13	0.950
O7—C8	1.449 (3)	C14—C15	1.382 (3)
O10—C11	1.425 (2)	C14—H14	0.950
O10—C9	1.438 (2)	C15—C16	1.379 (3)
N1—C5	1.458 (3)	C15—H15	0.950
N1—C2	1.459 (3)	C16—C17	1.381 (3)
N1—H1	0.91 (2)	C16—H16	0.950
N2—C4	1.513 (3)	C17—H17	0.950
C2—C6	1.531 (3)	C18—H181	0.980
C2—C3	1.563 (2)	C18—H182	0.980
C2—H2	1.000	C18—H183	0.980
C3—C9	1.531 (3)	C19—H191	0.980
C3—C4	1.549 (3)	C19—H192	0.980
C3—H3	1.000	C19—H193	0.980
C4—C19	1.527 (3)	C20—C21	1.389 (3)
C4—C5	1.550 (2)	C20—C25	1.398 (3)
C5—C20	1.508 (3)	C21—C22	1.415 (4)
C5—H5	1.000	C21—H21	0.950
C8—H81	0.980	C22—C23	1.371 (4)
C8—H82	0.980	C22—H22	0.950
C8—H83	0.980	C23—C24	1.376 (4)
C9—C18	1.518 (3)	C23—H23	0.950
C9—H9	1.000	C24—C25	1.387 (3)
C11—C12	1.506 (3)	C24—H24	0.950
C11—H111	0.990	C25—H25	0.950
C11—H112	0.990

C6—O7—C8	117.12 (17)	C12—C11—H112	109.7
C11—O10—C9	113.63 (14)	H111—C11—H112	108.2
C5—N1—C2	107.02 (15)	C13—C12—C17	118.41 (18)
C5—N1—H1	112.6 (15)	C13—C12—C11	122.03 (17)
C2—N1—H1	113.2 (15)	C17—C12—C11	119.55 (18)
O2—N2—O1	123.8 (2)	C12—C13—C14	120.6 (2)
O2—N2—C4	118.6 (2)	C12—C13—H13	119.7
O1—N2—C4	117.55 (17)	C14—C13—H13	119.7
N1—C2—C6	111.97 (16)	C15—C14—C13	120.3 (2)
N1—C2—C3	105.08 (16)	C15—C14—H14	119.9
C6—C2—C3	112.47 (16)	C13—C14—H14	119.9
N1—C2—H2	109.1	C16—C15—C14	119.5 (2)
C6—C2—H2	109.1	C16—C15—H15	120.3
C3—C2—H2	109.1	C14—C15—H15	120.3
C9—C3—C4	113.88 (15)	C15—C16—C17	119.98 (19)
C9—C3—C2	115.41 (16)	C15—C16—H16	120.0
C2—C3—C4	103.10 (15)	C17—C16—H16	120.0
C9—C3—H3	108.0	C16—C17—C12	121.2 (2)
C4—C3—H3	108.0	C16—C17—H17	119.4
C2—C3—H3	108.0	C12—C17—H17	119.4
N2—C4—C19	109.53 (17)	C9—C18—H181	109.5
N2—C4—C3	110.24 (15)	C9—C18—H182	109.5
C19—C4—C3	115.27 (17)	H181—C18—H182	109.5
N2—C4—C5	107.69 (16)	C9—C18—H183	109.5
C19—C4—C5	111.75 (16)	H181—C18—H183	109.5
C3—C4—C5	101.94 (14)	H182—C18—H183	109.5
N1—C5—C20	115.12 (16)	C4—C19—H191	109.5
N1—C5—C4	99.45 (16)	C4—C19—H192	109.5
C20—C5—C4	115.71 (16)	H191—C19—H192	109.5
N1—C5—H5	108.7	C4—C19—H193	109.5
C20—C5—H5	108.7	H191—C19—H193	109.5
C4—C5—H5	108.7	H192—C19—H193	109.5
O6—C6—O7	123.68 (19)	C21—C20—C25	118.7 (2)
O6—C6—C2	124.3 (2)	C21—C20—C5	122.1 (2)
O7—C6—C2	111.97 (16)	C25—C20—C5	119.26 (18)
O7—C8—H81	109.5	C20—C21—C22	119.4 (2)
O7—C8—H82	109.5	C20—C21—H21	120.3
H81—C8—H82	109.5	C22—C21—H21	120.3
O7—C8—H83	109.5	C23—C22—C21	120.5 (2)
H81—C8—H83	109.5	C23—C22—H22	119.8
H82—C8—H83	109.5	C21—C22—H22	119.8
O10—C9—C18	110.50 (18)	C22—C23—C24	120.6 (2)
O10—C9—C3	104.44 (15)	C22—C23—H23	119.7
C18—C9—C3	113.42 (17)	C24—C23—H23	119.7
O10—C9—H9	109.4	C23—C24—C25	119.3 (3)
C18—C9—H9	109.4	C23—C24—H24	120.3
C3—C9—H9	109.4	C25—C24—H24	120.3
O10—C11—C12	109.70 (16)	C24—C25—C20	121.5 (2)
O10—C11—H111	109.7	C24—C25—H25	119.2
C12—C11—H111	109.7	C20—C25—H25	119.2
O10—C11—H112	109.7

C5—N1—C2—C6	93.37 (18)	C3—C2—C6—O7	−62.9 (2)
C5—N1—C2—C3	−29.00 (19)	C11—O10—C9—C18	78.8 (2)
N1—C2—C3—C9	−126.00 (18)	C11—O10—C9—C3	−158.85 (17)
C6—C2—C3—C9	111.9 (2)	C4—C3—C9—O10	55.7 (2)
N1—C2—C3—C4	−1.20 (18)	C2—C3—C9—O10	174.69 (16)
C6—C2—C3—C4	−123.25 (17)	C4—C3—C9—C18	176.07 (18)
O2—N2—C4—C19	8.5 (3)	C2—C3—C9—C18	−64.9 (2)
O1—N2—C4—C19	−174.99 (18)	C9—O10—C11—C12	−176.35 (17)
O2—N2—C4—C3	136.31 (19)	O10—C11—C12—C13	−10.6 (3)
O1—N2—C4—C3	−47.1 (2)	O10—C11—C12—C17	167.90 (18)
O2—N2—C4—C5	−113.3 (2)	C17—C12—C13—C14	−1.4 (4)
O1—N2—C4—C5	63.3 (2)	C11—C12—C13—C14	177.1 (2)
C9—C3—C4—N2	−91.70 (19)	C12—C13—C14—C15	0.3 (4)
C2—C3—C4—N2	142.51 (15)	C13—C14—C15—C16	1.2 (4)
C9—C3—C4—C19	32.9 (2)	C14—C15—C16—C17	−1.5 (4)
C2—C3—C4—C19	−92.87 (18)	C15—C16—C17—C12	0.3 (3)
C9—C3—C4—C5	154.16 (16)	C13—C12—C17—C16	1.2 (3)
C2—C3—C4—C5	28.37 (18)	C11—C12—C17—C16	−177.42 (19)
C2—N1—C5—C20	171.08 (15)	N1—C5—C20—C21	−19.4 (3)
C2—N1—C5—C4	46.76 (17)	C4—C5—C20—C21	95.9 (2)
N2—C4—C5—N1	−161.45 (15)	N1—C5—C20—C25	160.85 (17)
C19—C4—C5—N1	78.2 (2)	C4—C5—C20—C25	−83.9 (2)
C3—C4—C5—N1	−45.43 (17)	C25—C20—C21—C22	0.2 (3)
N2—C4—C5—C20	74.6 (2)	C5—C20—C21—C22	−179.60 (18)
C19—C4—C5—C20	−45.7 (2)	C20—C21—C22—C23	0.0 (3)
C3—C4—C5—C20	−169.34 (16)	C21—C22—C23—C24	0.3 (4)
C8—O7—C6—O6	0.1 (3)	C22—C23—C24—C25	−0.8 (3)
C8—O7—C6—C2	−176.78 (19)	C23—C24—C25—C20	1.0 (3)
N1—C2—C6—O6	2.2 (3)	C21—C20—C25—C24	−0.7 (3)
C3—C2—C6—O6	120.2 (2)	C5—C20—C25—C24	179.12 (18)
N1—C2—C6—O7	179.00 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.91 (2)	2.46 (2)	2.778 (2)	101.1 (16)
N1—H1···O6ⁱ	0.91 (2)	2.39 (2)	3.278 (2)	164 (2)

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆N₂O₅
M_r	398.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.245 (2), 8.4082 (17), 26.6330 (15)
β (°)	94.802 (11)
V (Å³)	2063.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.32 × 0.22

Data collection
Diffractometer	Rigaku AFC-5R diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5348, 4719, 2920
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.142, 1.06
No. of reflections	4719
No. of parameters	269
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.19

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 and PLATON (Spek, 2001).

Selected geometric parameters (Å, º) top

N1—C5	1.458 (3)	C2—C3	1.563 (2)
N1—C2	1.459 (3)	C3—C4	1.549 (3)
N2—C4	1.513 (3)	C4—C5	1.550 (2)

C5—N1—C2	107.02 (15)	C3—C4—C5	101.94 (14)
N1—C2—C3	105.08 (16)	N1—C5—C4	99.45 (16)
C2—C3—C4	103.10 (15)

C5—N1—C2—C3	−29.00 (19)	C2—N1—C5—C4	46.76 (17)
N1—C2—C3—C4	−1.20 (18)	C3—C4—C5—N1	−45.43 (17)
C2—C3—C4—C5	28.37 (18)