2-{2-[3-(3,5-Dimethoxy­phen­yl)-1,2,4-oxadiazol-5-yl]phen­oxy}-N-(2,6-di­methyl­phen­yl)acetamide

Li, H.-L.; Wang, H.-B.; Yin, J.; Kang, S.-S.; Zeng, H.-S.

doi:10.1107/S1600536807049501

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2-{2-[3-(3,5-Dimethoxyphenyl)-1,2,4-oxadiazol-5-yl]phenoxy}-N-(2,6-dimethylphenyl)acetamide

H.-L. Li, H.-B. Wang, J. Yin, S.-S. Kang and H.-S. Zeng

In the molecule of the title compound, C₂₆H₂₅N₃O₅, the dihedral angles between the oxadiazole ring and the adjacent benzene rings are 3.56 (12) and 5.72 (11)°. Intramolecular N—H

O and C—H

O hydrogen bonds result in the formation of four more five-membered planar rings, which are nearly coplanar with the adjacent rings.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049501/hk2336sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049501/hk2336Isup2.hkl Contains datablock I

CCDC reference: 667354

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.007 Å
R factor = 0.083
wR factor = 0.179
Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.668
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.67 e/A   
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C21    -   C22     ..       5.07 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.55
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7

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

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

Comment top

1,2,4-Oxadiazole derivatives possess biological properties such as intrinsic analgesic (Terashita et al., 2002) and antipicornaviral (Romero, 2001) effects. As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).

Rings A (C3—C8), B (N1/N2/O3/C9/C10), C (C11—C16) and D (C19—C24) are, of course, planar and the dihedral angles between them are A/B = 3.54 (3)°, A/C = 5.65 (2)°, B/C = 5.56 (3)° and C/D = 68.17 (2)°.

The intramolecular N—H···O and C—H···O hydrogen bonds (Table 1) cause to the formation of four five-membered planar rings E (N2/H6A/C6/C7/C9), F (N1/N2/O3/C9/C10), G (O4/N3/H3A/C17/C18) and H (N3/C19/C20/C26/H26A) (Fig. 1), in which they are also nearly co-planar with the adjacent rings, as can be deduced from the dihedral angles of A/E = 2.20 (3)°, B/E = 1.52 (2)°, B/F = 3.03 (3)°, C/F = 2.54 (2)° and D/H = 2.48 (3)°. Hydrogen bonds may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Romero (2001); Terashita et al. (2002). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, (I), potassium carbonate (15 mmol) and 5-(2-hydroxyphenyl)-3-(3,5-dimethoxyl)-phenyl-1,2,4-oxadiazole (10 mmol) were added, respectively, to the solution of 2-chloro-N-(2,6-dimethylphenyl)- acetamide (10 mmol) in acetone (100 ml). The resulting mixture was refluxed for 12 h. After cooling and filtering, the crude title compound was obtained and purified by recrystalization from ethyl acetate. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield; 3.62 g, 78.8%, m.p. 419–420 K).

Structure description top

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).

For related literature, see: Romero (2001); Terashita et al. (2002). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

2-{2-[3-(3,5-Dimethoxyphenyl)-1,2,4-oxadiazol-5-yl]phenoxy}- N-(2,6-dimethylphenyl)acetamide top

Crystal data top

C₂₆H₂₅N₃O₅	Z = 2
M_r = 459.49	F(000) = 484
Triclinic, P1	D_x = 1.334 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3200 (15) Å	Cell parameters from 25 reflections
b = 12.630 (3) Å	θ = 9–13°
c = 13.106 (3) Å	µ = 0.09 mm⁻¹
α = 95.37 (3)°	T = 294 K
β = 101.06 (3)°	Block, colorless
γ = 103.48 (3)°	0.30 × 0.10 × 0.10 mm
V = 1144.2 (5) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2028 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.047
Graphite monochromator	θ_max = 26.0°, θ_min = 1.6°
ω/2θ scans	h = −9→8
Absorption correction: ψ scan (North et al., 1968)	k = −15→15
T_min = 0.989, T_max = 0.991	l = 0→16
4846 measured reflections	3 standard reflections every 120 min
4473 independent reflections	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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.037P)² + 0.89P] where P = (F_o² + 2F_c²)/3
4473 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₆H₂₅N₃O₅	γ = 103.48 (3)°
M_r = 459.49	V = 1144.2 (5) Å³
Triclinic, P1	Z = 2
a = 7.3200 (15) Å	Mo Kα radiation
b = 12.630 (3) Å	µ = 0.09 mm⁻¹
c = 13.106 (3) Å	T = 294 K
α = 95.37 (3)°	0.30 × 0.10 × 0.10 mm
β = 101.06 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2028 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.047
T_min = 0.989, T_max = 0.991	3 standard reflections every 120 min
4846 measured reflections	intensity decay: none
4473 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.06	Δρ_max = 0.67 e Å⁻³
4473 reflections	Δρ_min = −0.37 e Å⁻³
289 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	0.3738 (5)	−0.2031 (3)	0.7085 (3)	0.0770 (11)
O2	0.6959 (4)	0.1635 (3)	0.8227 (2)	0.0674 (9)
O3	0.1682 (4)	0.1486 (2)	0.3487 (2)	0.0544 (8)
O4	0.0182 (4)	0.1649 (2)	0.1575 (2)	0.0618 (9)
O5	0.1340 (5)	0.4105 (3)	0.0536 (2)	0.073
N1	0.2816 (5)	0.1636 (3)	0.4531 (2)	0.0578 (11)
N2	0.1300 (5)	−0.0156 (3)	0.3976 (2)	0.0449 (9)
N3	0.2857 (5)	0.3462 (3)	0.1901 (3)	0.0601 (11)
H3A	0.2880	0.2884	0.2197	0.072*
C1	0.2473 (8)	−0.2889 (4)	0.6317 (5)	0.102 (2)
H1B	0.2419	−0.3582	0.6571	0.153*
H1C	0.2935	−0.2899	0.5680	0.153*
H1D	0.1208	−0.2766	0.6182	0.153*
C2	0.7412 (7)	0.2758 (4)	0.8085 (4)	0.0839 (18)
H2B	0.8343	0.3184	0.8688	0.126*
H2C	0.6266	0.3016	0.8001	0.126*
H2D	0.7935	0.2834	0.7470	0.126*
C3	0.5675 (6)	0.0903 (4)	0.7431 (3)	0.0533 (12)
C4	0.5289 (6)	−0.0181 (4)	0.7583 (3)	0.0601 (13)
H4A	0.5905	−0.0374	0.8200	0.072*
C5	0.4015 (6)	−0.0979 (4)	0.6841 (3)	0.0526 (12)
C6	0.3069 (6)	−0.0714 (4)	0.5914 (3)	0.0514 (11)
H6A	0.2181	−0.1256	0.5414	0.062*
C7	0.3476 (6)	0.0364 (4)	0.5754 (3)	0.0448 (10)
C8	0.4766 (6)	0.1189 (4)	0.6499 (3)	0.0493 (11)
H8A	0.5019	0.1918	0.6380	0.059*
C9	0.2518 (6)	0.0642 (3)	0.4753 (3)	0.0462 (11)
C10	0.0835 (6)	0.0413 (3)	0.3235 (3)	0.0436 (10)
C11	−0.0464 (5)	−0.0039 (3)	0.2205 (3)	0.0385 (10)
C12	−0.1374 (6)	−0.1151 (3)	0.2040 (3)	0.0543 (12)
H12A	−0.1090	−0.1578	0.2560	0.065*
C13	−0.2688 (7)	−0.1638 (4)	0.1123 (3)	0.0579 (13)
H13A	−0.3291	−0.2386	0.1018	0.070*
C14	−0.3091 (7)	−0.0993 (4)	0.0366 (3)	0.0615 (13)
H14A	−0.4016	−0.1307	−0.0246	0.074*
C15	−0.2177 (6)	0.0085 (3)	0.0487 (3)	0.0516 (12)
H15A	−0.2460	0.0502	−0.0042	0.062*
C16	−0.0824 (6)	0.0568 (3)	0.1396 (3)	0.0426 (10)
C17	−0.0099 (6)	0.2329 (3)	0.0789 (3)	0.0551 (12)
H17A	−0.1362	0.2469	0.0720	0.066*
H17B	−0.0031	0.1962	0.0118	0.066*
C18	0.1413 (7)	0.3383 (4)	0.1084 (3)	0.0623 (14)
C19	0.4371 (7)	0.4428 (3)	0.2324 (4)	0.0619 (14)
C20	0.4323 (9)	0.5036 (4)	0.3245 (4)	0.0835 (18)
C21	0.5882 (11)	0.5932 (4)	0.3679 (5)	0.107 (3)
H21A	0.5907	0.6348	0.4308	0.129*
C22	0.7353 (10)	0.6200 (4)	0.3197 (5)	0.103 (3)
H22A	0.8349	0.6820	0.3495	0.124*
C23	0.7467 (9)	0.5593 (5)	0.2266 (5)	0.096
H23A	0.8520	0.5785	0.1959	0.115*
C24	0.5918 (8)	0.4688 (4)	0.1826 (4)	0.0690 (15)
C25	0.5993 (8)	0.4040 (4)	0.0840 (5)	0.0942 (19)
H25A	0.7151	0.4367	0.0623	0.141*
H25B	0.4895	0.4034	0.0302	0.141*
H25C	0.5981	0.3299	0.0955	0.141*
C26	0.2561 (8)	0.4750 (5)	0.3734 (5)	0.097
H26A	0.1659	0.4099	0.3333	0.146*
H26B	0.1961	0.5349	0.3733	0.146*
H26C	0.2959	0.4622	0.4444	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.085 (3)	0.067 (2)	0.069 (2)	0.014 (2)	−0.0115 (19)	0.0325 (19)
O2	0.055 (2)	0.082 (2)	0.0471 (18)	0.0023 (18)	−0.0171 (16)	0.0205 (17)
O3	0.067 (2)	0.0465 (18)	0.0357 (15)	0.0081 (15)	−0.0181 (14)	0.0108 (13)
O4	0.072 (2)	0.0492 (18)	0.0425 (17)	−0.0050 (16)	−0.0215 (15)	0.0210 (14)
O5	0.073	0.073	0.073	0.019	0.016	0.011
N1	0.069 (3)	0.061 (2)	0.0306 (19)	0.013 (2)	−0.0184 (18)	0.0103 (17)
N2	0.042 (2)	0.054 (2)	0.0353 (18)	0.0088 (17)	−0.0011 (16)	0.0151 (16)
N3	0.061 (2)	0.043 (2)	0.059 (2)	−0.0001 (19)	−0.018 (2)	0.0212 (18)
C1	0.101 (5)	0.079 (4)	0.112 (5)	0.015 (4)	−0.014 (4)	0.042 (4)
C2	0.071 (4)	0.082 (4)	0.067 (3)	−0.017 (3)	−0.021 (3)	0.021 (3)
C3	0.043 (3)	0.068 (3)	0.044 (2)	0.015 (2)	−0.006 (2)	0.016 (2)
C4	0.054 (3)	0.081 (4)	0.042 (2)	0.021 (3)	−0.010 (2)	0.029 (2)
C5	0.049 (3)	0.068 (3)	0.046 (3)	0.022 (2)	0.006 (2)	0.028 (2)
C6	0.043 (3)	0.064 (3)	0.043 (2)	0.011 (2)	−0.004 (2)	0.020 (2)
C7	0.041 (2)	0.064 (3)	0.032 (2)	0.019 (2)	0.0002 (19)	0.015 (2)
C8	0.047 (3)	0.060 (3)	0.039 (2)	0.013 (2)	−0.001 (2)	0.019 (2)
C9	0.049 (3)	0.055 (3)	0.032 (2)	0.015 (2)	−0.005 (2)	0.016 (2)
C10	0.045 (3)	0.043 (2)	0.038 (2)	0.010 (2)	−0.0029 (19)	0.0126 (19)
C11	0.034 (2)	0.041 (2)	0.035 (2)	0.0071 (19)	−0.0035 (18)	0.0101 (17)
C12	0.060 (3)	0.054 (3)	0.043 (2)	0.011 (2)	−0.002 (2)	0.017 (2)
C13	0.070 (3)	0.047 (3)	0.043 (3)	−0.004 (2)	0.002 (2)	0.011 (2)
C14	0.061 (3)	0.065 (3)	0.041 (2)	−0.002 (3)	−0.012 (2)	0.010 (2)
C15	0.052 (3)	0.052 (3)	0.038 (2)	−0.001 (2)	−0.010 (2)	0.013 (2)
C16	0.045 (3)	0.038 (2)	0.036 (2)	0.002 (2)	−0.0033 (19)	0.0117 (18)
C17	0.050 (3)	0.050 (3)	0.057 (3)	0.004 (2)	−0.008 (2)	0.030 (2)
C18	0.062 (3)	0.054 (3)	0.062 (3)	0.006 (2)	−0.013 (2)	0.040 (2)
C19	0.062 (3)	0.036 (3)	0.066 (3)	−0.002 (2)	−0.023 (3)	0.017 (2)
C20	0.108 (5)	0.050 (3)	0.069 (4)	0.014 (3)	−0.030 (3)	0.010 (3)
C21	0.177 (7)	0.047 (3)	0.062 (4)	0.010 (4)	−0.036 (4)	0.007 (3)
C22	0.117 (6)	0.050 (4)	0.106 (5)	−0.009 (3)	−0.037 (4)	0.041 (4)
C23	0.096	0.096	0.096	0.025	0.021	0.014
C24	0.064 (3)	0.034 (3)	0.084 (4)	−0.007 (2)	−0.023 (3)	0.013 (3)
C25	0.080 (4)	0.075 (4)	0.120 (5)	0.008 (3)	0.011 (4)	0.024 (4)
C26	0.097	0.097	0.097	0.025	0.021	0.014

Geometric parameters (Å, º) top

O1—C5	1.374 (5)	C10—C11	1.471 (5)
O1—C1	1.419 (6)	C11—C12	1.384 (5)
O2—C3	1.365 (5)	C11—C16	1.386 (5)
O2—C2	1.418 (5)	C12—C13	1.374 (5)
O3—C10	1.332 (4)	C12—H12A	0.9300
O3—N1	1.428 (4)	C13—C14	1.374 (5)
O4—C16	1.366 (4)	C13—H13A	0.9300
O4—C17	1.417 (4)	C14—C15	1.350 (5)
O5—C18	1.217 (4)	C14—H14A	0.9300
N1—C9	1.294 (5)	C15—C16	1.379 (5)
N2—C10	1.302 (4)	C15—H15A	0.9300
N2—C9	1.374 (5)	C17—C18	1.484 (5)
N3—C18	1.331 (5)	C17—H17A	0.9700
N3—C19	1.425 (5)	C17—H17B	0.9700
N3—H3A	0.8600	C19—C20	1.379 (7)
C1—H1B	0.9600	C19—C24	1.402 (7)
C1—H1C	0.9600	C20—C21	1.391 (7)
C1—H1D	0.9600	C20—C26	1.533 (8)
C2—H2B	0.9600	C21—C22	1.343 (9)
C2—H2C	0.9600	C21—H21A	0.9300
C2—H2D	0.9600	C22—C23	1.406 (8)
C3—C4	1.374 (6)	C22—H22A	0.9300
C3—C8	1.395 (5)	C23—C24	1.395 (7)
C4—C5	1.364 (6)	C23—H23A	0.9300
C4—H4A	0.9300	C24—C25	1.481 (7)
C5—C6	1.389 (5)	C25—H25A	0.9600
C6—C7	1.370 (5)	C25—H25B	0.9600
C6—H6A	0.9300	C25—H25C	0.9600
C7—C8	1.388 (5)	C26—H26A	0.9600
C7—C9	1.478 (5)	C26—H26B	0.9600
C8—H8A	0.9300	C26—H26C	0.9600

C5—O1—C1	117.2 (3)	C14—C13—C12	118.5 (4)
C3—O2—C2	117.4 (3)	C14—C13—H13A	120.8
C10—O3—N1	106.5 (3)	C12—C13—H13A	120.8
C16—O4—C17	119.8 (3)	C15—C14—C13	121.6 (4)
C9—N1—O3	102.4 (3)	C15—C14—H14A	119.2
C10—N2—C9	102.3 (3)	C13—C14—H14A	119.2
C18—N3—C19	125.1 (3)	C14—C15—C16	119.9 (4)
C18—N3—H3A	117.4	C14—C15—H15A	120.0
C19—N3—H3A	117.4	C16—C15—H15A	120.0
O1—C1—H1B	109.5	O4—C16—C15	123.6 (3)
O1—C1—H1C	109.5	O4—C16—C11	116.2 (3)
H1B—C1—H1C	109.5	C15—C16—C11	120.1 (4)
O1—C1—H1D	109.5	O4—C17—C18	109.1 (3)
H1B—C1—H1D	109.5	O4—C17—H17A	109.9
H1C—C1—H1D	109.5	C18—C17—H17A	109.9
O2—C2—H2B	109.5	O4—C17—H17B	109.9
O2—C2—H2C	109.5	C18—C17—H17B	109.9
H2B—C2—H2C	109.5	H17A—C17—H17B	108.3
O2—C2—H2D	109.5	O5—C18—N3	123.2 (4)
H2B—C2—H2D	109.5	O5—C18—C17	118.9 (4)
H2C—C2—H2D	109.5	N3—C18—C17	117.8 (3)
O2—C3—C4	116.1 (4)	C20—C19—C24	122.2 (5)
O2—C3—C8	124.5 (4)	C20—C19—N3	118.8 (5)
C4—C3—C8	119.5 (4)	C24—C19—N3	118.8 (5)
C5—C4—C3	120.9 (4)	C19—C20—C21	117.7 (6)
C5—C4—H4A	119.6	C19—C20—C26	120.3 (5)
C3—C4—H4A	119.6	C21—C20—C26	121.9 (6)
C4—C5—O1	115.6 (4)	C22—C21—C20	120.5 (6)
C4—C5—C6	120.8 (4)	C22—C21—H21A	119.8
O1—C5—C6	123.6 (4)	C20—C21—H21A	119.8
C7—C6—C5	118.3 (4)	C21—C22—C23	123.5 (6)
C7—C6—H6A	120.8	C21—C22—H22A	118.3
C5—C6—H6A	120.8	C23—C22—H22A	118.3
C6—C7—C8	121.8 (4)	C24—C23—C22	116.6 (6)
C6—C7—C9	118.4 (4)	C24—C23—H23A	121.7
C8—C7—C9	119.8 (4)	C22—C23—H23A	121.7
C7—C8—C3	118.7 (4)	C23—C24—C19	119.5 (5)
C7—C8—H8A	120.6	C23—C24—C25	117.7 (6)
C3—C8—H8A	120.6	C19—C24—C25	122.8 (4)
N1—C9—N2	115.6 (3)	C24—C25—H25A	109.5
N1—C9—C7	122.8 (4)	C24—C25—H25B	109.5
N2—C9—C7	121.6 (4)	H25A—C25—H25B	109.5
N2—C10—O3	113.2 (3)	C24—C25—H25C	109.5
N2—C10—C11	125.5 (4)	H25A—C25—H25C	109.5
O3—C10—C11	121.3 (3)	H25B—C25—H25C	109.5
C12—C11—C16	118.4 (3)	C20—C26—H26A	109.5
C12—C11—C10	117.1 (3)	C20—C26—H26B	109.5
C16—C11—C10	124.6 (4)	H26A—C26—H26B	109.5
C13—C12—C11	121.3 (4)	C20—C26—H26C	109.5
C13—C12—H12A	119.3	H26A—C26—H26C	109.5
C11—C12—H12A	119.3	H26B—C26—H26C	109.5

C10—O3—N1—C9	0.8 (4)	C10—C11—C12—C13	176.6 (4)
C2—O2—C3—C4	178.9 (4)	C11—C12—C13—C14	−0.2 (7)
C2—O2—C3—C8	−1.0 (7)	C12—C13—C14—C15	2.6 (8)
O2—C3—C4—C5	179.4 (4)	C13—C14—C15—C16	−1.0 (8)
C8—C3—C4—C5	−0.7 (7)	C17—O4—C16—C15	−2.0 (6)
C3—C4—C5—O1	−179.6 (4)	C17—O4—C16—C11	180.0 (4)
C3—C4—C5—C6	−0.2 (7)	C14—C15—C16—O4	179.1 (4)
C1—O1—C5—C4	−177.9 (5)	C14—C15—C16—C11	−2.9 (7)
C1—O1—C5—C6	2.7 (7)	C12—C11—C16—O4	−176.7 (4)
C4—C5—C6—C7	1.3 (7)	C10—C11—C16—O4	3.0 (6)
O1—C5—C6—C7	−179.4 (4)	C12—C11—C16—C15	5.2 (6)
C5—C6—C7—C8	−1.3 (6)	C10—C11—C16—C15	−175.1 (4)
C5—C6—C7—C9	178.0 (4)	C16—O4—C17—C18	−168.9 (4)
C6—C7—C8—C3	0.4 (6)	C19—N3—C18—O5	8.0 (8)
C9—C7—C8—C3	−178.9 (4)	C19—N3—C18—C17	−176.6 (5)
O2—C3—C8—C7	−179.5 (4)	O4—C17—C18—O5	−175.4 (4)
C4—C3—C8—C7	0.6 (7)	O4—C17—C18—N3	9.0 (6)
O3—N1—C9—N2	−0.4 (5)	C18—N3—C19—C20	103.5 (6)
O3—N1—C9—C7	177.2 (4)	C18—N3—C19—C24	−80.6 (6)
C10—N2—C9—N1	−0.2 (5)	C24—C19—C20—C21	−0.1 (7)
C10—N2—C9—C7	−177.8 (4)	N3—C19—C20—C21	175.6 (4)
C6—C7—C9—N1	−179.8 (4)	C24—C19—C20—C26	177.4 (4)
C8—C7—C9—N1	−0.4 (6)	N3—C19—C20—C26	−6.9 (7)
C6—C7—C9—N2	−2.4 (6)	C19—C20—C21—C22	1.4 (8)
C8—C7—C9—N2	177.0 (4)	C26—C20—C21—C22	−176.0 (5)
C9—N2—C10—O3	0.8 (5)	C20—C21—C22—C23	−2.4 (9)
C9—N2—C10—C11	−180.0 (4)	C21—C22—C23—C24	1.9 (9)
N1—O3—C10—N2	−1.1 (5)	C22—C23—C24—C19	−0.4 (7)
N1—O3—C10—C11	179.7 (4)	C22—C23—C24—C25	179.5 (5)
N2—C10—C11—C12	5.0 (6)	C20—C19—C24—C23	−0.4 (7)
O3—C10—C11—C12	−175.9 (4)	N3—C19—C24—C23	−176.1 (4)
N2—C10—C11—C16	−174.7 (4)	C20—C19—C24—C25	179.7 (4)
O3—C10—C11—C16	4.4 (6)	N3—C19—C24—C25	4.0 (7)
C16—C11—C12—C13	−3.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.86	2.17	2.582 (5)	109
C6—H6A···N2	0.93	2.52	2.850 (5)	101
C12—H12A···N2	0.93	2.53	2.864 (5)	102
C26—H26A···N3	0.96	2.37	2.846 (7)	110

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅N₃O₅
M_r	459.49
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.3200 (15), 12.630 (3), 13.106 (3)
α, β, γ (°)	95.37 (3), 101.06 (3), 103.48 (3)
V (Å³)	1144.2 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.989, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	4846, 4473, 2028
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.179, 1.06
No. of reflections	4473
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.37

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.8600	2.1700	2.582 (5)	109.00
C6—H6A···N2	0.9300	2.5200	2.850 (5)	101.00
C12—H12A···N2	0.9300	2.5300	2.864 (5)	102.00
C26—H26A···N3	0.9600	2.3700	2.846 (7)	110.00

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