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

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

doi:10.1107/S1600536807052270

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

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

In the title compound, C₂₆H₂₆N₄O₃, a bifurcated intramolecular N—H

(O,N) hydrogen bond helps to establish the molecular conformation. The dihedral angles between the oxadiazole ring and the adjacent benzene rings are 14.10 (19) and 17.90 (18)° for the central benzene ring and the (dimethylamino)phenyl ring, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052270/hb2606sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052270/hb2606Isup2.hkl Contains datablock I

CCDC reference: 674660

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.077
wR factor = 0.178
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H2B    ..  H4B     ..       1.84 Ang.

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

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   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 out studies in this area, we report here the synthesis and crystal structure of the title compound, (I), (Fig. 1).

The dihedral angles between the N2/O1/C10/N3/C9 ring and its adjacent bezene rings are 14.10 (19) and 17.90 (18)° for the C11 and C3 rings, respectively.

An intramolecular, bifurcated N—H···(N,O) hydrogen bond (Table 1) helps to establish the molecular conformation of (I).

Related literature top

For background, see: Romero (2001); Terashita et al. (2002).

Experimental top

2-Chloro-N-(2,6-dimethylphenyl)acetamide (10 mmol) was dissolved in acetone (100 ml) and potassium carbonate (15 mmol) was added. Then, 5-(2-hydroxyphenyl)-3-(4-N,N-dimethyl)-phenyl- 1,2,4-oxadiazole (10 mmol) was added to the reaction. 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. Colourless blocks of (I) were obtained by slow evaporation of an ethanol solution.

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: SHELXS97 (Sheldrick, 1997).

Figures top

Fig. 1. A view of the molecular structure of (I) showing 30% displacement ellipsoids (arbitrary spheres for the H atoms). Dashed lines indicate the hydrogen bonds.

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

Crystal data top

C₂₆H₂₆N₄O₃	Z = 2
M_r = 442.51	F(000) = 468
Triclinic, P1	D_x = 1.300 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9900 (18) Å	Cell parameters from 25 reflections
b = 9.0330 (18) Å	θ = 9–13°
c = 15.445 (3) Å	µ = 0.09 mm⁻¹
α = 83.01 (3)°	T = 293 K
β = 79.76 (3)°	Block, colorless
γ = 66.54 (3)°	0.30 × 0.20 × 0.10 mm
V = 1130.4 (4) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2692 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 26.0°, θ_min = 1.3°
ω/2θ scans	h = −10→11
Absorption correction: ψ scan (North et al., 1968)	k = −10→11
T_min = 0.974, T_max = 0.991	l = 0→19
4419 measured reflections	3 standard reflections every 200 reflections
4419 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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.018P)² + 2P] where P = (F_o² + 2F_c²)/3
4419 reflections	(Δ/σ)_max < 0.001
293 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₆H₂₆N₄O₃	γ = 66.54 (3)°
M_r = 442.51	V = 1130.4 (4) Å³
Triclinic, P1	Z = 2
a = 8.9900 (18) Å	Mo Kα radiation
b = 9.0330 (18) Å	µ = 0.09 mm⁻¹
c = 15.445 (3) Å	T = 293 K
α = 83.01 (3)°	0.30 × 0.20 × 0.10 mm
β = 79.76 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2692 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.974, T_max = 0.991	3 standard reflections every 200 reflections
4419 measured reflections	intensity decay: none
4419 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.03	Δρ_max = 0.50 e Å⁻³
4419 reflections	Δρ_min = −0.43 e Å⁻³
293 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	1.1192 (3)	0.2794 (3)	0.45197 (18)	0.067
O2	1.3415 (3)	0.4254 (4)	0.2256 (2)	0.0914 (11)
O3	1.2793 (3)	0.6748 (3)	0.03292 (18)	0.0696 (8)
N1	0.3072 (4)	0.8914 (5)	0.3050 (3)	0.0988 (14)
N2	0.9452 (4)	0.3580 (5)	0.4585 (2)	0.0774 (11)
N3	1.0722 (4)	0.4657 (4)	0.3431 (2)	0.0581 (8)
N4	1.1088 (3)	0.6202 (4)	0.1492 (2)	0.0552 (8)
H4A	1.1046	0.5840	0.2033	0.066*
C1	0.1610 (5)	0.8702 (7)	0.3466 (4)	0.115 (2)
H1A	0.1627	0.7702	0.3303	0.172*
H1B	0.0673	0.9582	0.3280	0.172*
H1C	0.1549	0.8678	0.4094	0.172*
C2	0.2944 (6)	1.0093 (6)	0.2336 (3)	0.0933 (16)
H2B	0.3948	1.0267	0.2196	0.140*
H2C	0.2057	1.1090	0.2500	0.140*
H2D	0.2740	0.9719	0.1831	0.140*
C3	0.4591 (5)	0.7886 (5)	0.3270 (3)	0.0651 (10)
C4	0.5996 (5)	0.8191 (5)	0.2957 (3)	0.0720 (12)
H4B	0.5927	0.9107	0.2592	0.086*
C5	0.7495 (5)	0.7138 (5)	0.3185 (3)	0.0643 (10)
H5A	0.8421	0.7366	0.2973	0.077*
C6	0.7651 (4)	0.5774 (5)	0.3714 (2)	0.0558 (9)
C7	0.6260 (5)	0.5489 (5)	0.4033 (3)	0.0683 (11)
H7A	0.6337	0.4577	0.4403	0.082*
C8	0.4748 (5)	0.6523 (5)	0.3816 (3)	0.0707 (11)
H8A	0.3826	0.6297	0.4042	0.085*
C9	0.9276 (5)	0.4658 (5)	0.3923 (2)	0.0566 (9)
C10	1.1844 (5)	0.3506 (5)	0.3835 (2)	0.0577 (9)
C11	1.3619 (5)	0.2919 (5)	0.3645 (3)	0.0637 (10)
C12	1.4409 (5)	0.3316 (5)	0.2846 (3)	0.0679 (11)
C13	1.6095 (5)	0.2761 (6)	0.2669 (3)	0.0818 (14)
H13A	1.6604	0.3045	0.2134	0.098*
C14	1.7009 (5)	0.1783 (6)	0.3296 (3)	0.0862 (14)
H14A	1.8146	0.1402	0.3183	0.103*
C15	1.6277 (5)	0.1367 (6)	0.4075 (3)	0.0837 (14)
H15A	1.6918	0.0700	0.4489	0.100*
C16	1.4578 (5)	0.1921 (5)	0.4267 (3)	0.0696 (11)
H16A	1.4087	0.1628	0.4806	0.084*
C17	1.4010 (4)	0.5052 (5)	0.1516 (3)	0.0656 (11)
H17A	1.4829	0.4271	0.1122	0.079*
H17B	1.4504	0.5719	0.1701	0.079*
C18	1.2550 (4)	0.6091 (5)	0.1056 (2)	0.0556 (9)
C19	0.9582 (4)	0.6882 (4)	0.1122 (2)	0.0496 (8)
C20	0.8857 (4)	0.5827 (4)	0.1007 (2)	0.0550 (9)
C21	0.7401 (5)	0.6480 (5)	0.0645 (3)	0.0667 (11)
H21A	0.6889	0.5809	0.0555	0.080*
C22	0.6711 (5)	0.8103 (6)	0.0420 (3)	0.0760 (13)
H22A	0.5747	0.8516	0.0171	0.091*
C23	0.7425 (5)	0.9115 (5)	0.0558 (3)	0.0724 (12)
H23A	0.6928	1.0213	0.0407	0.087*
C24	0.8885 (4)	0.8547 (4)	0.0920 (2)	0.0554 (9)
C25	0.9578 (5)	0.9673 (5)	0.1131 (3)	0.0716 (11)
H25A	0.8938	1.0752	0.0929	0.107*
H25B	1.0688	0.9365	0.0844	0.107*
H25C	0.9557	0.9632	0.1756	0.107*
C26	0.9577 (5)	0.4057 (5)	0.1276 (3)	0.0721 (12)
H26A	1.0581	0.3811	0.1503	0.108*
H26B	0.9792	0.3434	0.0774	0.108*
H26C	0.8817	0.3794	0.1723	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.067	0.067	0.067	−0.026	−0.009	−0.004
O2	0.0446 (15)	0.131 (3)	0.080 (2)	−0.0251 (17)	−0.0207 (14)	0.0476 (19)
O3	0.0594 (16)	0.0797 (19)	0.0633 (17)	−0.0231 (14)	−0.0103 (13)	0.0086 (15)
N1	0.056 (2)	0.115 (3)	0.109 (3)	−0.018 (2)	−0.028 (2)	0.025 (3)
N2	0.051 (2)	0.096 (3)	0.072 (2)	−0.0196 (19)	−0.0139 (17)	0.017 (2)
N3	0.0488 (17)	0.065 (2)	0.0557 (19)	−0.0150 (15)	−0.0166 (14)	0.0045 (15)
N4	0.0425 (16)	0.066 (2)	0.0545 (18)	−0.0178 (14)	−0.0153 (13)	0.0073 (15)
C1	0.048 (3)	0.151 (5)	0.133 (5)	−0.028 (3)	−0.027 (3)	0.021 (4)
C2	0.078 (3)	0.088 (4)	0.112 (4)	−0.024 (3)	−0.042 (3)	0.020 (3)
C3	0.051 (2)	0.074 (3)	0.066 (3)	−0.015 (2)	−0.0146 (19)	−0.008 (2)
C4	0.056 (2)	0.069 (3)	0.080 (3)	−0.013 (2)	−0.014 (2)	0.002 (2)
C5	0.053 (2)	0.069 (3)	0.067 (3)	−0.021 (2)	−0.0071 (19)	−0.002 (2)
C6	0.049 (2)	0.062 (2)	0.052 (2)	−0.0168 (18)	−0.0066 (16)	−0.0055 (18)
C7	0.061 (2)	0.076 (3)	0.068 (3)	−0.026 (2)	−0.015 (2)	0.006 (2)
C8	0.055 (2)	0.081 (3)	0.078 (3)	−0.026 (2)	−0.020 (2)	0.003 (2)
C9	0.054 (2)	0.064 (2)	0.049 (2)	−0.0192 (18)	−0.0127 (17)	0.0008 (18)
C10	0.058 (2)	0.067 (2)	0.047 (2)	−0.0236 (19)	−0.0141 (17)	0.0106 (18)
C11	0.052 (2)	0.066 (3)	0.062 (2)	−0.0055 (19)	−0.0252 (19)	−0.0010 (19)
C12	0.047 (2)	0.079 (3)	0.069 (3)	−0.013 (2)	−0.0200 (19)	0.008 (2)
C13	0.046 (2)	0.102 (4)	0.084 (3)	−0.011 (2)	−0.021 (2)	0.001 (3)
C14	0.053 (3)	0.093 (4)	0.096 (4)	−0.008 (2)	−0.026 (2)	0.007 (3)
C15	0.066 (3)	0.079 (3)	0.091 (4)	−0.002 (2)	−0.042 (3)	0.004 (3)
C16	0.067 (3)	0.069 (3)	0.065 (3)	−0.014 (2)	−0.026 (2)	0.007 (2)
C17	0.046 (2)	0.080 (3)	0.062 (2)	−0.018 (2)	−0.0085 (18)	0.007 (2)
C18	0.047 (2)	0.066 (2)	0.053 (2)	−0.0202 (18)	−0.0104 (17)	−0.0003 (18)
C19	0.0403 (18)	0.057 (2)	0.050 (2)	−0.0147 (16)	−0.0126 (15)	0.0002 (16)
C20	0.056 (2)	0.055 (2)	0.057 (2)	−0.0242 (18)	−0.0067 (17)	−0.0036 (17)
C21	0.060 (2)	0.084 (3)	0.070 (3)	−0.040 (2)	−0.015 (2)	−0.005 (2)
C22	0.053 (2)	0.091 (3)	0.081 (3)	−0.021 (2)	−0.030 (2)	0.010 (3)
C23	0.060 (2)	0.065 (3)	0.084 (3)	−0.010 (2)	−0.029 (2)	0.004 (2)
C24	0.054 (2)	0.053 (2)	0.056 (2)	−0.0153 (17)	−0.0133 (17)	−0.0032 (17)
C25	0.085 (3)	0.062 (3)	0.073 (3)	−0.029 (2)	−0.025 (2)	−0.002 (2)
C26	0.080 (3)	0.061 (3)	0.078 (3)	−0.032 (2)	−0.009 (2)	0.001 (2)

Geometric parameters (Å, º) top

O1—C10	1.338 (4)	C10—C11	1.453 (5)
O1—N2	1.427 (4)	C11—C12	1.392 (5)
O2—C12	1.358 (4)	C11—C16	1.395 (5)
O2—C17	1.415 (4)	C12—C13	1.380 (5)
O3—C18	1.230 (4)	C13—C14	1.376 (6)
N1—C3	1.387 (5)	C13—H13A	0.9300
N1—C2	1.423 (6)	C14—C15	1.352 (6)
N1—C1	1.431 (6)	C14—H14A	0.9300
N2—C9	1.308 (5)	C15—C16	1.391 (6)
N3—C10	1.312 (4)	C15—H15A	0.9300
N3—C9	1.384 (5)	C16—H16A	0.9300
N4—C18	1.338 (4)	C17—C18	1.516 (5)
N4—C19	1.437 (4)	C17—H17A	0.9700
N4—H4A	0.8600	C17—H17B	0.9700
C1—H1A	0.9600	C19—C20	1.393 (5)
C1—H1B	0.9600	C19—C24	1.399 (5)
C1—H1C	0.9600	C20—C21	1.392 (5)
C2—H2B	0.9600	C20—C26	1.503 (5)
C2—H2C	0.9600	C21—C22	1.372 (6)
C2—H2D	0.9600	C21—H21A	0.9300
C3—C8	1.378 (6)	C22—C23	1.362 (6)
C3—C4	1.390 (5)	C22—H22A	0.9300
C4—C5	1.383 (5)	C23—C24	1.398 (5)
C4—H4B	0.9300	C23—H23A	0.9300
C5—C6	1.365 (5)	C24—C25	1.478 (5)
C5—H5A	0.9300	C25—H25A	0.9600
C6—C7	1.371 (5)	C25—H25B	0.9600
C6—C9	1.473 (5)	C25—H25C	0.9600
C7—C8	1.381 (5)	C26—H26A	0.9600
C7—H7A	0.9300	C26—H26B	0.9600
C8—H8A	0.9300	C26—H26C	0.9600

C10—O1—N2	107.7 (3)	C14—C13—C12	118.9 (5)
C12—O2—C17	121.2 (3)	C14—C13—H13A	120.5
C3—N1—C2	120.6 (4)	C12—C13—H13A	120.5
C3—N1—C1	121.0 (4)	C15—C14—C13	120.8 (4)
C2—N1—C1	118.0 (4)	C15—C14—H14A	119.6
C9—N2—O1	102.0 (3)	C13—C14—H14A	119.6
C10—N3—C9	102.8 (3)	C14—C15—C16	121.1 (4)
C18—N4—C19	124.7 (3)	C14—C15—H15A	119.5
C18—N4—H4A	117.6	C16—C15—H15A	119.5
C19—N4—H4A	117.6	C15—C16—C11	119.4 (4)
N1—C1—H1A	109.5	C15—C16—H16A	120.3
N1—C1—H1B	109.5	C11—C16—H16A	120.3
H1A—C1—H1B	109.5	O2—C17—C18	106.7 (3)
N1—C1—H1C	109.5	O2—C17—H17A	110.4
H1A—C1—H1C	109.5	C18—C17—H17A	110.4
H1B—C1—H1C	109.5	O2—C17—H17B	110.4
N1—C2—H2B	109.5	C18—C17—H17B	110.4
N1—C2—H2C	109.5	H17A—C17—H17B	108.6
H2B—C2—H2C	109.5	O3—C18—N4	125.8 (3)
N1—C2—H2D	109.5	O3—C18—C17	118.6 (3)
H2B—C2—H2D	109.5	N4—C18—C17	115.5 (3)
H2C—C2—H2D	109.5	C20—C19—C24	123.0 (3)
C8—C3—N1	120.5 (4)	C20—C19—N4	117.2 (3)
C8—C3—C4	117.8 (4)	C24—C19—N4	119.7 (3)
N1—C3—C4	121.7 (4)	C21—C20—C19	117.4 (3)
C5—C4—C3	120.3 (4)	C21—C20—C26	120.4 (4)
C5—C4—H4B	119.8	C19—C20—C26	122.2 (3)
C3—C4—H4B	119.8	C22—C21—C20	120.8 (4)
C6—C5—C4	121.7 (4)	C22—C21—H21A	119.6
C6—C5—H5A	119.2	C20—C21—H21A	119.6
C4—C5—H5A	119.2	C23—C22—C21	120.7 (4)
C5—C6—C7	117.9 (4)	C23—C22—H22A	119.7
C5—C6—C9	120.1 (4)	C21—C22—H22A	119.7
C7—C6—C9	122.0 (4)	C22—C23—C24	121.7 (4)
C6—C7—C8	121.6 (4)	C22—C23—H23A	119.1
C6—C7—H7A	119.2	C24—C23—H23A	119.1
C8—C7—H7A	119.2	C23—C24—C19	116.3 (4)
C3—C8—C7	120.7 (4)	C23—C24—C25	121.1 (4)
C3—C8—H8A	119.6	C19—C24—C25	122.4 (3)
C7—C8—H8A	119.6	C24—C25—H25A	109.5
N2—C9—N3	115.2 (3)	C24—C25—H25B	109.5
N2—C9—C6	122.1 (3)	H25A—C25—H25B	109.5
N3—C9—C6	122.7 (3)	C24—C25—H25C	109.5
N3—C10—O1	112.2 (3)	H25A—C25—H25C	109.5
N3—C10—C11	130.0 (3)	H25B—C25—H25C	109.5
O1—C10—C11	117.7 (3)	C20—C26—H26A	109.5
C12—C11—C16	118.3 (4)	C20—C26—H26B	109.5
C12—C11—C10	121.7 (3)	H26A—C26—H26B	109.5
C16—C11—C10	120.0 (4)	C20—C26—H26C	109.5
O2—C12—C13	122.8 (4)	H26A—C26—H26C	109.5
O2—C12—C11	115.7 (3)	H26B—C26—H26C	109.5
C13—C12—C11	121.5 (4)

C10—O1—N2—C9	0.6 (4)	C16—C11—C12—O2	178.2 (4)
C2—N1—C3—C8	−165.1 (5)	C10—C11—C12—O2	−1.2 (6)
C1—N1—C3—C8	7.8 (7)	C16—C11—C12—C13	−0.8 (7)
C2—N1—C3—C4	15.3 (7)	C10—C11—C12—C13	179.8 (4)
C1—N1—C3—C4	−171.8 (5)	O2—C12—C13—C14	−178.3 (5)
C8—C3—C4—C5	0.7 (6)	C11—C12—C13—C14	0.6 (7)
N1—C3—C4—C5	−179.7 (4)	C12—C13—C14—C15	0.0 (8)
C3—C4—C5—C6	0.5 (7)	C13—C14—C15—C16	−0.3 (8)
C4—C5—C6—C7	−1.4 (6)	C14—C15—C16—C11	0.1 (7)
C4—C5—C6—C9	178.3 (4)	C12—C11—C16—C15	0.4 (6)
C5—C6—C7—C8	1.2 (6)	C10—C11—C16—C15	179.9 (4)
C9—C6—C7—C8	−178.5 (4)	C12—O2—C17—C18	−175.1 (4)
N1—C3—C8—C7	179.5 (4)	C19—N4—C18—O3	11.1 (6)
C4—C3—C8—C7	−0.9 (6)	C19—N4—C18—C17	−168.8 (3)
C6—C7—C8—C3	−0.1 (7)	O2—C17—C18—O3	−171.0 (4)
O1—N2—C9—N3	0.1 (5)	O2—C17—C18—N4	8.9 (5)
O1—N2—C9—C6	179.3 (3)	C18—N4—C19—C20	112.1 (4)
C10—N3—C9—N2	−0.8 (5)	C18—N4—C19—C24	−69.8 (5)
C10—N3—C9—C6	−180.0 (4)	C24—C19—C20—C21	2.2 (5)
C5—C6—C9—N2	162.5 (4)	N4—C19—C20—C21	−179.8 (3)
C7—C6—C9—N2	−17.8 (6)	C24—C19—C20—C26	−176.4 (4)
C5—C6—C9—N3	−18.4 (6)	N4—C19—C20—C26	1.6 (5)
C7—C6—C9—N3	161.3 (4)	C19—C20—C21—C22	−0.5 (6)
C9—N3—C10—O1	1.2 (4)	C26—C20—C21—C22	178.2 (4)
C9—N3—C10—C11	−179.2 (4)	C20—C21—C22—C23	−1.0 (7)
N2—O1—C10—N3	−1.2 (4)	C21—C22—C23—C24	0.8 (7)
N2—O1—C10—C11	179.1 (3)	C22—C23—C24—C19	0.8 (6)
N3—C10—C11—C12	−14.3 (7)	C22—C23—C24—C25	−175.1 (4)
O1—C10—C11—C12	165.3 (4)	C20—C19—C24—C23	−2.4 (5)
N3—C10—C11—C16	166.3 (4)	N4—C19—C24—C23	179.7 (3)
O1—C10—C11—C16	−14.1 (6)	C20—C19—C24—C25	173.5 (4)
C17—O2—C12—C13	−16.0 (7)	N4—C19—C24—C25	−4.4 (5)
C17—O2—C12—C11	165.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2	0.86	2.10	2.513 (4)	109
N4—H4A···N3	0.86	2.32	3.170 (4)	171

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆N₄O₃
M_r	442.51
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.9900 (18), 9.0330 (18), 15.445 (3)
α, β, γ (°)	83.01 (3), 79.76 (3), 66.54 (3)
V (Å³)	1130.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.974, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	4419, 4419, 2692
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.179, 1.03
No. of reflections	4419
No. of parameters	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.43

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