Methyl 5′-acetyl-2′-amino-6′-methyl-2-oxospiro­[indoline-3,4′-4H-pyran]-3′-carboxyl­ate

Shishkina, S.V.; Shishkin, O.V.; Redkin, R.G.; Shemchuk, L.A.; Chernykh, V.P.

doi:10.1107/S1600536807027547

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Methyl 5′-acetyl-2′-amino-6′-methyl-2-oxospiro[indoline-3,4′-4H-pyran]-3′-carboxylate

S. V. Shishkina, O. V. Shishkin, R. G. Redkin, L. A. Shemchuk and V. P. Chernykh

In the title compound, C₁₈H₁₈N₂O₅, the two spiro-fused cyclic fragments are planar. The planar system is stabilized by an intramolecular N—H

O hydrogen bond. In the crystal packing, molecules are connected by intermolecular N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027547/kp2112sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027547/kp2112Isup2.hkl Contains datablock I

CCDC reference: 654939

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.047
wR factor = 0.149
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.66 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C14    -   C15     ..       7.22 su

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.51 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C17
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          R

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Spiro-cyclic derivatives of 2-oxindole are interesting objects for searching of new physiologically active substances (Cingolant et al., 1989, Urbahns et al., 2000). However, such compounds containing the 2-amino-4H-pyrane fragment have not been investigated. In this paper we report the molecular and crystal structure of the spiro[indolin-3,4-(5-acetyl-2-amino-3-carbethoxy-6- methyl-4H-pyran)]-2-one (Fig. 1) which can be considered as a potential melatonin analogue with a rigid etanamide side chain. Dihydroindolone fragment is planar within 0.01 Å and spiro-joined to the dihydropyrane ring; esterified carboxyl group and the C18, N2, and C16 atoms are co-planar within 0.03 Å and are turned with respect to the bicyclic fragment for 116.2 (2) ° (the C1—C6—C7—C9 torsion angle). The formation of hydrogen bond promotes the elongation of the C11—C12 and C13—O3 bonds (Table 1) in comparison with their mean values (Bürgi & Dunitz, 1994) 1.320 Å and 1.210 Å, respectively and the shortening of the C11—N2 and C12—C13 bonds (the mean value are 1.336 Å and 1.455 Å, respectively). The repulsion between substituents at the C9—C10 double bond (the shortened intramolecular contacts H17c···C10 2.81 Å, H17c···C18 2.76 Å, H18b···C16 2.63 Å, H18c···C17 2.64 Å [the sum of van der Waals radii is 2.87 Å (Zefirov & Zorky, 1995)], C18···C17 3.19 Å (3.42 Å) leads to an increase of the C9—C10—C18 bond angle up to 128.6 (2) °. The formation of the N2—H2Na···O3 intramolecular hydrogen bond (Table 2) supports the coplanarity of the carboxyl group and dihydropyrane ring. In the crystal molecules of (I) are connected by the intermolecular hydrogen bonds N1—H1N···O1' and N2—H2Nb···O1' (Table 2, Fig. 2).

Related literature top

For related literature, see: Cingolant et al. (1989); Urbahns et al. (2000); Zefirov & Zorky (1995).

For related literature, see: Bürgi & Dunitz (1994).

Experimental top

A solution of isatin (0.01 mol), triethanolamine (1.3 ml, 0.01 mol) and pentane-2,4-dione (1.01 ml, 0.01 mol) in absolute ethanol (10.0 ml) were gradually added to the cyano-acetic acid ethyl ester (1.1 ml, 0.01 mol). The resulting reaction mixture was refluxed for 2 h. The mixture was allowed to form the precipitate. The resulting precipitate was filtered, washed with hexane, and recrystallized from the ethanol and DMF mixture (1:1) and dried. Yield 0.22 g (65%), m.p. 508 K. ¹H NMR (DMSO-d₆) δ p.p.m.: 065 t (3H, OCH₂CH₃), 1.80 s (3H, CH₃), 2.05 s (3H, COCH₃), 3.65 q (2H, OCH₂CH₃), 6.65 d (1H), 6.80 t (1H), 6.98 d (1H), 7.05 t (1H), 7.72 s (1H, NH₂, D₂O) exchangeable), 10.25 s (1H, NH, D₂O exchangeable.). Analysis, required for C₁₈H₁₈N₂O₅: C 63.15; H 5.30; N 8.18%; found: C63.15; H 5.30; N 8.18%.

Structure description top

For related literature, see: Cingolant et al. (1989); Urbahns et al. (2000); Zefirov & Zorky (1995).

For related literature, see: Bürgi & Dunitz (1994).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (or SHELXTL-Plus?)(Sheldrick, 1998); program(s) used to refine structure: SHELXTL (or SHELXTL-Plus?); molecular graphics: XP (Siemens, 1998); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of the title compound with atomic membering. All atoms are shown with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing is stabilized by N—H···O hydrogen bonds.

Methyl 5'-acetyl-2'-amino-6'-methyl-2-oxospiro[indoline-3,4'-4H-pyran]-3'-carboxylate top

Crystal data top

C₁₈H₁₈N₂O₅	F(000) = 1440
M_r = 342.34	D_x = 1.305 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.5506 (9) Å	Cell parameters from 6306 reflections
b = 10.6729 (4) Å	θ = 3–35°
c = 15.8285 (7) Å	µ = 0.10 mm⁻¹
β = 122.818 (3)°	T = 293 K
V = 3485.5 (2) Å³	Plate, colourless
Z = 8	0.30 × 0.10 × 0.05 mm

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	2240 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.031
Graphite monochromator	θ_max = 25.0°, θ_min = 2.9°
Detector resolution: 16.1827 pixels mm^-1	h = −29→29
ω scans	k = −12→12
10420 measured reflections	l = −18→17
3018 independent reflections

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: difference Fourier map
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0851P)² + 1.3474P] where P = (F_o² + 2F_c²)/3
3018 reflections	(Δ/σ)_max < 0.001
241 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₁₈N₂O₅	V = 3485.5 (2) Å³
M_r = 342.34	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.5506 (9) Å	µ = 0.10 mm⁻¹
b = 10.6729 (4) Å	T = 293 K
c = 15.8285 (7) Å	0.30 × 0.10 × 0.05 mm
β = 122.818 (3)°

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	2240 reflections with I > 2σ(I)
10420 measured reflections	R_int = 0.031
3018 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.32 e Å⁻³
3018 reflections	Δρ_min = −0.21 e Å⁻³
241 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
O1	0.08678 (6)	0.67104 (13)	0.34768 (10)	0.0526 (4)
O2	0.28466 (6)	0.64340 (14)	0.44108 (11)	0.0602 (4)
O3	0.19920 (8)	0.99077 (15)	0.32023 (13)	0.0770 (5)
O4	0.10457 (7)	0.89331 (14)	0.22049 (12)	0.0695 (5)
O5	0.09930 (8)	0.40131 (17)	0.26489 (14)	0.0787 (5)
N1	0.03680 (7)	0.65486 (15)	0.17652 (12)	0.0483 (4)
H1N	−0.0044 (13)	0.663 (2)	0.1598 (19)	0.070 (7)*
N2	0.29878 (9)	0.8478 (2)	0.45134 (15)	0.0626 (5)
H2NB	0.3365 (13)	0.830 (2)	0.511 (2)	0.067 (7)*
H2NA	0.2827 (13)	0.926 (3)	0.430 (2)	0.084 (9)*
C1	0.05499 (9)	0.64990 (16)	0.10680 (14)	0.0457 (4)
C2	0.01655 (10)	0.64695 (19)	0.00309 (15)	0.0584 (6)
H2	−0.0284	0.6499	−0.0306	0.070*
C3	0.04697 (12)	0.6395 (2)	−0.04904 (16)	0.0641 (6)
H3	0.0221	0.6381	−0.1189	0.077*
C4	0.11360 (12)	0.6342 (2)	0.00091 (16)	0.0610 (6)
H4	0.1330	0.6278	−0.0356	0.073*
C5	0.15193 (10)	0.63820 (18)	0.10521 (15)	0.0510 (5)
H5	0.1969	0.6347	0.1389	0.061*
C6	0.12235 (8)	0.64741 (16)	0.15742 (13)	0.0431 (4)
C7	0.15141 (8)	0.65374 (16)	0.27042 (13)	0.0388 (4)
C8	0.08823 (8)	0.66018 (17)	0.27184 (14)	0.0431 (4)
C9	0.18856 (8)	0.53477 (17)	0.32161 (13)	0.0433 (4)
C10	0.24992 (9)	0.53452 (19)	0.39961 (15)	0.0525 (5)
C11	0.25668 (9)	0.75611 (19)	0.40164 (14)	0.0487 (5)
C12	0.19375 (8)	0.76803 (18)	0.32151 (13)	0.0450 (4)
C13	0.16859 (10)	0.89299 (19)	0.28959 (15)	0.0545 (5)
C14	0.07229 (14)	1.0115 (3)	0.1836 (2)	0.0975 (10)
H14B	0.0863	1.0522	0.1437	0.117*
H14A	0.0824	1.0660	0.2393	0.117*
C15	−0.00001 (19)	0.9856 (4)	0.1196 (4)	0.1426 (16)
H15C	−0.0092	0.9300	0.0657	0.214*
H15B	−0.0230	1.0630	0.0923	0.214*
H15A	−0.0135	0.9476	0.1603	0.214*
C16	0.15250 (9)	0.41441 (18)	0.27901 (14)	0.0492 (5)
C17	0.17974 (14)	0.3148 (2)	0.2462 (2)	0.0835 (8)
H17C	0.2221	0.3394	0.2628	0.125*
H17B	0.1518	0.3032	0.1748	0.125*
H17A	0.1828	0.2377	0.2798	0.125*
C18	0.29125 (12)	0.4255 (3)	0.45825 (19)	0.0831 (8)
H18C	0.3242	0.4135	0.4438	0.125*
H18B	0.2649	0.3516	0.4399	0.125*
H18A	0.3113	0.4414	0.5288	0.125*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0338 (7)	0.0759 (9)	0.0445 (8)	−0.0015 (6)	0.0188 (6)	−0.0062 (6)
O2	0.0326 (7)	0.0714 (10)	0.0538 (9)	0.0016 (6)	0.0085 (6)	−0.0094 (7)
O3	0.0651 (10)	0.0576 (10)	0.0789 (11)	−0.0174 (8)	0.0198 (9)	−0.0042 (8)
O4	0.0492 (9)	0.0526 (9)	0.0694 (10)	0.0000 (6)	0.0078 (8)	0.0017 (7)
O5	0.0548 (10)	0.0833 (12)	0.0920 (13)	−0.0154 (8)	0.0359 (9)	−0.0148 (9)
N1	0.0248 (8)	0.0650 (10)	0.0432 (9)	−0.0036 (6)	0.0108 (7)	−0.0015 (7)
N2	0.0408 (10)	0.0775 (14)	0.0499 (11)	−0.0170 (9)	0.0117 (9)	−0.0105 (9)
C1	0.0374 (9)	0.0490 (10)	0.0394 (10)	−0.0074 (7)	0.0134 (8)	−0.0021 (8)
C2	0.0434 (11)	0.0633 (13)	0.0440 (11)	−0.0091 (9)	0.0076 (9)	−0.0012 (9)
C3	0.0713 (15)	0.0683 (14)	0.0374 (11)	−0.0151 (10)	0.0195 (11)	−0.0039 (9)
C4	0.0712 (15)	0.0679 (14)	0.0466 (12)	−0.0111 (10)	0.0336 (11)	−0.0055 (9)
C5	0.0486 (11)	0.0551 (12)	0.0480 (11)	−0.0079 (8)	0.0252 (10)	−0.0044 (8)
C6	0.0375 (9)	0.0460 (10)	0.0387 (10)	−0.0069 (7)	0.0161 (8)	−0.0045 (7)
C7	0.0289 (8)	0.0465 (10)	0.0363 (9)	−0.0033 (7)	0.0145 (7)	−0.0028 (7)
C8	0.0319 (9)	0.0502 (10)	0.0416 (10)	−0.0021 (7)	0.0163 (8)	−0.0034 (7)
C9	0.0382 (9)	0.0521 (11)	0.0393 (9)	0.0024 (7)	0.0209 (8)	−0.0015 (8)
C10	0.0417 (10)	0.0595 (12)	0.0466 (11)	0.0061 (8)	0.0176 (9)	−0.0054 (9)
C11	0.0361 (9)	0.0635 (13)	0.0435 (10)	−0.0077 (8)	0.0197 (8)	−0.0082 (9)
C12	0.0336 (9)	0.0581 (11)	0.0391 (9)	−0.0063 (8)	0.0170 (8)	−0.0054 (8)
C13	0.0484 (11)	0.0555 (12)	0.0477 (11)	−0.0098 (9)	0.0183 (9)	−0.0058 (9)
C14	0.0754 (17)	0.0617 (15)	0.098 (2)	0.0061 (13)	0.0102 (15)	0.0115 (14)
C15	0.090 (2)	0.113 (3)	0.158 (4)	0.031 (2)	0.024 (2)	0.027 (2)
C16	0.0481 (11)	0.0542 (11)	0.0415 (10)	−0.0006 (8)	0.0218 (9)	0.0040 (8)
C17	0.0882 (18)	0.0638 (15)	0.104 (2)	−0.0079 (13)	0.0556 (17)	−0.0230 (14)
C18	0.0654 (15)	0.0803 (17)	0.0650 (15)	0.0258 (13)	0.0102 (12)	−0.0028 (12)

Geometric parameters (Å, º) top

O1—C8	1.226 (2)	C6—C7	1.526 (2)
O2—C11	1.358 (2)	C7—C9	1.516 (2)
O2—C10	1.379 (2)	C7—C12	1.520 (2)
O3—C13	1.222 (2)	C7—C8	1.565 (2)
O4—C13	1.343 (2)	C9—C10	1.333 (3)
O4—C14	1.435 (3)	C9—C16	1.497 (3)
O5—C16	1.208 (2)	C10—C18	1.491 (3)
N1—C8	1.345 (2)	C11—C12	1.374 (3)
N1—C1	1.398 (3)	C12—C13	1.441 (3)
N1—H1N	0.90 (3)	C14—C15	1.518 (5)
N2—C11	1.328 (2)	C14—H14B	0.9700
N2—H2NB	0.91 (3)	C14—H14A	0.9700
N2—H2NA	0.90 (3)	C15—H15C	0.9600
C1—C2	1.381 (3)	C15—H15B	0.9600
C1—C6	1.393 (3)	C15—H15A	0.9600
C2—C3	1.383 (3)	C16—C17	1.491 (3)
C2—H2	0.9300	C17—H17C	0.9600
C3—C4	1.379 (3)	C17—H17B	0.9600
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.389 (3)	C18—H18C	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.368 (3)	C18—H18A	0.9600
C5—H5	0.9300

C11—O2—C10	119.97 (14)	C9—C10—C18	128.6 (2)
C13—O4—C14	118.56 (17)	O2—C10—C18	108.93 (17)
C8—N1—C1	112.32 (15)	N2—C11—O2	110.06 (17)
C8—N1—H1N	123.3 (16)	N2—C11—C12	127.1 (2)
C1—N1—H1N	124.1 (16)	O2—C11—C12	122.82 (16)
C11—N2—H2NB	119.2 (15)	C11—C12—C13	117.59 (17)
C11—N2—H2NA	114.4 (18)	C11—C12—C7	121.29 (17)
H2NB—N2—H2NA	125 (2)	C13—C12—C7	121.10 (15)
C2—C1—C6	121.10 (19)	O3—C13—O4	121.16 (19)
C2—C1—N1	129.37 (18)	O3—C13—C12	126.63 (18)
C6—C1—N1	109.52 (16)	O4—C13—C12	112.20 (16)
C1—C2—C3	117.93 (19)	O4—C14—C15	107.5 (2)
C1—C2—H2	121.0	O4—C14—H14B	110.2
C3—C2—H2	121.0	C15—C14—H14B	110.2
C4—C3—C2	121.10 (19)	O4—C14—H14A	110.2
C4—C3—H3	119.5	C15—C14—H14A	110.2
C2—C3—H3	119.5	H14B—C14—H14A	108.5
C3—C4—C5	120.6 (2)	C14—C15—H15C	109.5
C3—C4—H4	119.7	C14—C15—H15B	109.5
C5—C4—H4	119.7	H15C—C15—H15B	109.5
C6—C5—C4	118.74 (19)	C14—C15—H15A	109.5
C6—C5—H5	120.6	H15C—C15—H15A	109.5
C4—C5—H5	120.6	H15B—C15—H15A	109.5
C5—C6—C1	120.49 (17)	O5—C16—C17	119.8 (2)
C5—C6—C7	130.34 (16)	O5—C16—C9	119.91 (18)
C1—C6—C7	109.16 (15)	C17—C16—C9	120.08 (18)
C9—C7—C12	110.36 (14)	C16—C17—H17C	109.5
C9—C7—C6	110.66 (14)	C16—C17—H17B	109.5
C12—C7—C6	114.17 (14)	H17C—C17—H17B	109.5
C9—C7—C8	110.05 (14)	C16—C17—H17A	109.5
C12—C7—C8	110.76 (14)	H17C—C17—H17A	109.5
C6—C7—C8	100.45 (13)	H17B—C17—H17A	109.5
O1—C8—N1	126.49 (17)	C10—C18—H18C	109.5
O1—C8—C7	124.99 (16)	C10—C18—H18B	109.5
N1—C8—C7	108.50 (16)	H18C—C18—H18B	109.5
C10—C9—C16	120.72 (17)	C10—C18—H18A	109.5
C10—C9—C7	123.15 (16)	H18C—C18—H18A	109.5
C16—C9—C7	116.12 (14)	H18B—C18—H18A	109.5
C9—C10—O2	122.41 (17)

C8—N1—C1—C2	−178.18 (19)	C6—C7—C9—C16	−52.80 (19)
C8—N1—C1—C6	2.1 (2)	C8—C7—C9—C16	57.31 (19)
C6—C1—C2—C3	1.0 (3)	C16—C9—C10—O2	−179.83 (16)
N1—C1—C2—C3	−178.70 (19)	C7—C9—C10—O2	0.7 (3)
C1—C2—C3—C4	0.5 (3)	C16—C9—C10—C18	−2.4 (3)
C2—C3—C4—C5	−1.0 (3)	C7—C9—C10—C18	178.2 (2)
C3—C4—C5—C6	0.1 (3)	C11—O2—C10—C9	−0.8 (3)
C4—C5—C6—C1	1.4 (3)	C11—O2—C10—C18	−178.72 (19)
C4—C5—C6—C7	−179.93 (18)	C10—O2—C11—N2	−178.78 (17)
C2—C1—C6—C5	−2.0 (3)	C10—O2—C11—C12	1.0 (3)
N1—C1—C6—C5	177.77 (16)	N2—C11—C12—C13	−3.3 (3)
C2—C1—C6—C7	179.12 (16)	O2—C11—C12—C13	177.05 (17)
N1—C1—C6—C7	−1.15 (19)	N2—C11—C12—C7	178.69 (18)
C5—C6—C7—C9	−62.6 (2)	O2—C11—C12—C7	−1.0 (3)
C1—C6—C7—C9	116.19 (16)	C9—C7—C12—C11	0.8 (2)
C5—C6—C7—C12	62.6 (2)	C6—C7—C12—C11	−124.59 (19)
C1—C6—C7—C12	−118.60 (16)	C8—C7—C12—C11	122.91 (18)
C5—C6—C7—C8	−178.84 (18)	C9—C7—C12—C13	−177.20 (16)
C1—C6—C7—C8	−0.05 (18)	C6—C7—C12—C13	57.4 (2)
C1—N1—C8—O1	176.39 (18)	C8—C7—C12—C13	−55.1 (2)
C1—N1—C8—C7	−2.1 (2)	C14—O4—C13—O3	−0.6 (3)
C9—C7—C8—O1	66.1 (2)	C14—O4—C13—C12	178.2 (2)
C12—C7—C8—O1	−56.2 (2)	C11—C12—C13—O3	7.4 (3)
C6—C7—C8—O1	−177.25 (17)	C7—C12—C13—O3	−174.5 (2)
C9—C7—C8—N1	−115.41 (16)	C11—C12—C13—O4	−171.36 (18)
C12—C7—C8—N1	122.29 (16)	C7—C12—C13—O4	6.7 (3)
C6—C7—C8—N1	1.28 (18)	C13—O4—C14—C15	−171.6 (3)
C12—C7—C9—C10	−0.7 (2)	C10—C9—C16—O5	130.3 (2)
C6—C7—C9—C10	126.69 (19)	C7—C9—C16—O5	−50.2 (2)
C8—C7—C9—C10	−123.20 (19)	C10—C9—C16—C17	−54.7 (3)
C12—C7—C9—C16	179.85 (15)	C7—C9—C16—C17	124.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.90 (3)	1.96 (3)	2.850 (2)	168 (2)
N2—H2NA···O3	0.90 (3)	1.96 (3)	2.667 (3)	134 (2)
N2—H2NB···O1ⁱⁱ	0.91 (3)	2.00 (3)	2.892 (2)	166 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂O₅
M_r	342.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	24.5506 (9), 10.6729 (4), 15.8285 (7)
β (°)	122.818 (3)
V (Å³)	3485.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur3
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10420, 3018, 2240
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.149, 1.09
No. of reflections	3018
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXTL (or SHELXTL-Plus?)(Sheldrick, 1998), SHELXTL (or SHELXTL-Plus?), XP (Siemens, 1998), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.90 (3)	1.96 (3)	2.850 (2)	168 (2)
N2—H2NA···O3	0.90 (3)	1.96 (3)	2.667 (3)	134 (2)
N2—H2NB···O1ⁱⁱ	0.91 (3)	2.00 (3)	2.892 (2)	166 (2)

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

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