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

Wang, H.-B.; Yin, J.; Xing, Z.-T.

doi:10.1107/S1600536807036136

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

H.-B. Wang, J. Yin and Z.-T. Xing

In the title compound, C₂₅H₂₃N₃O₅S, a bifurcated intramolecular N—H

O,N hydrogen bond helps to establish the molecular conformation. The dihedral angles between the oxadiazole ring and its adjacent benzene rings are 24.50 (19) and 12.20 (18)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036136/hb2487sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036136/hb2487Isup2.hkl Contains datablock I

CCDC reference: 662406

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.075
wR factor = 0.178
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.61 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C9      ..       5.36 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C17     ..       5.36 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C25
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H11A   ..  H25A    ..       2.14 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
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        146

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   3 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
   1 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 N1/O1/C9/N2/C8 ring and its adjacent bezene rings are 24.50 (19) and 12.20 (18)° for the C2 and C10 rings, respectively.

An intramolecular, bifurcated N—H···(N,O) hydrogen bond (Table 1) helps to establish the molecular conformation of (I). Some short C—H···O and C—H···N contacts are also present.

Related literature top

For related literature, 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-methylsulfonyl)-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. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Structure description top

The dihedral angles between the N1/O1/C9/N2/C8 ring and its adjacent bezene rings are 24.50 (19) and 12.20 (18)° for the C2 and C10 rings, respectively.

An intramolecular, bifurcated N—H···(N,O) hydrogen bond (Table 1) helps to establish the molecular conformation of (I). Some short C—H···O and C—H···N contacts are also present.

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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; 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: PLATON (Spek, 2003).

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.

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

Crystal data top

C₂₅H₂₃N₃O₅S	F(000) = 2000
M_r = 477.52	D_x = 1.340 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 28.848 (6) Å	θ = 9–12°
b = 13.648 (3) Å	µ = 0.18 mm⁻¹
c = 13.562 (3) Å	T = 293 K
β = 117.58 (3)°	Block, colourless
V = 4733 (2) Å³	0.20 × 0.10 × 0.10 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	3927 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 = −35→31
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
T_min = 0.979, T_max = 0.983	l = 0→16
4737 measured reflections	3 standard reflections every 200 reflections
4643 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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.06P)² + P] where P = (F_o² + 2F_c²)/3
4643 reflections	(Δ/σ)_max < 0.001
283 parameters	Δρ_max = 0.34 e Å⁻³
146 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₅H₂₃N₃O₅S	V = 4733 (2) Å³
M_r = 477.52	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.848 (6) Å	µ = 0.18 mm⁻¹
b = 13.648 (3) Å	T = 293 K
c = 13.562 (3) Å	0.20 × 0.10 × 0.10 mm
β = 117.58 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3927 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.047
T_min = 0.979, T_max = 0.983	3 standard reflections every 200 reflections
4737 measured reflections	intensity decay: none
4643 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	146 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 0.97	Δρ_max = 0.34 e Å⁻³
4643 reflections	Δρ_min = −0.39 e Å⁻³
283 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
S	0.14194 (6)	0.18555 (9)	0.81078 (14)	0.0925 (5)
O1	0.16502 (17)	0.1933 (3)	0.9251 (4)	0.126
O2	0.11504 (16)	0.1004 (3)	0.7585 (4)	0.125
O3	−0.06215 (11)	0.6306 (2)	0.5510 (2)	0.060
O4	0.06199 (10)	0.8113 (2)	0.6481 (3)	0.0673 (9)
O5	0.19856 (11)	0.8304 (2)	0.7637 (3)	0.0934 (13)
N1	−0.04744 (14)	0.5304 (3)	0.5690 (3)	0.0643 (11)
N2	0.02244 (12)	0.6304 (2)	0.6536 (3)	0.0453 (9)
N3	0.14383 (11)	0.7053 (2)	0.7465 (3)	0.0481 (9)
H3A	0.1118	0.6884	0.7242	0.058*
C1	0.1908 (2)	0.2025 (4)	0.7674 (5)	0.108
H1C	0.2148	0.1485	0.7927	0.163*
H1D	0.2094	0.2624	0.7983	0.163*
H1E	0.1747	0.2059	0.6877	0.163*
C2	0.10088 (18)	0.2876 (3)	0.7563 (4)	0.0582 (12)
C3	0.04852 (19)	0.2760 (3)	0.6783 (4)	0.0619 (13)
H3B	0.0351	0.2137	0.6536	0.074*
C4	0.01671 (17)	0.3567 (3)	0.6378 (4)	0.0615 (12)
H4A	−0.0183	0.3489	0.5867	0.074*
C5	0.03657 (15)	0.4475 (3)	0.6726 (3)	0.0446 (10)
C6	0.08838 (15)	0.4603 (3)	0.7502 (3)	0.0514 (11)
H6A	0.1015	0.5231	0.7731	0.062*
C7	0.12050 (17)	0.3807 (3)	0.7934 (4)	0.0640 (13)
H7A	0.1551	0.3891	0.8469	0.077*
C8	0.00352 (17)	0.5356 (3)	0.6299 (3)	0.0468 (10)
C9	−0.01894 (15)	0.6851 (3)	0.6063 (3)	0.0463 (10)
C10	−0.02598 (14)	0.7885 (3)	0.5990 (3)	0.0460 (10)
C11	−0.07551 (15)	0.8299 (3)	0.5674 (4)	0.0607 (12)
H11A	−0.1043	0.7892	0.5476	0.073*
C12	−0.08211 (19)	0.9311 (4)	0.5653 (4)	0.0719 (14)
H12A	−0.1153	0.9575	0.5423	0.086*
C13	−0.04122 (19)	0.9897 (3)	0.5960 (4)	0.0657 (13)
H13A	−0.0456	1.0569	0.5992	0.079*
C14	0.00762 (17)	0.9529 (3)	0.6232 (3)	0.0576 (12)
H14A	0.0354	0.9958	0.6411	0.069*
C15	0.01587 (15)	0.8543 (3)	0.6243 (3)	0.0459 (10)
C16	0.10881 (14)	0.8666 (3)	0.6885 (4)	0.0538 (11)
H16A	0.1104	0.9126	0.7446	0.065*
H16B	0.1095	0.9037	0.6281	0.065*
C17	0.15441 (16)	0.7993 (3)	0.7373 (4)	0.0529 (12)
C18	0.18426 (14)	0.6307 (3)	0.7926 (3)	0.0416 (9)
C19	0.20946 (14)	0.6160 (3)	0.9060 (3)	0.0478 (10)
C20	0.24727 (16)	0.5436 (3)	0.9441 (4)	0.0659 (13)
H20A	0.2655	0.5334	1.0205	0.079*
C21	0.25960 (16)	0.4870 (3)	0.8786 (4)	0.0641 (13)
H21A	0.2854	0.4392	0.9087	0.077*
C22	0.23276 (17)	0.5023 (3)	0.7657 (4)	0.0633 (12)
H22A	0.2398	0.4620	0.7189	0.076*
C23	0.19522 (15)	0.5760 (3)	0.7186 (4)	0.0502 (11)
C24	0.16793 (17)	0.5935 (4)	0.5952 (4)	0.0819 (16)
H24A	0.1800	0.5468	0.5593	0.123*
H24B	0.1754	0.6586	0.5799	0.123*
H24C	0.1309	0.5862	0.5676	0.123*
C25	0.19565 (17)	0.6755 (3)	0.9839 (4)	0.0660 (13)
H25A	0.1686	0.7216	0.9413	0.099*
H25B	0.2261	0.7102	1.0363	0.099*
H25C	0.1836	0.6323	1.0231	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.1070 (12)	0.0509 (8)	0.0930 (12)	0.0056 (8)	0.0237 (10)	−0.0028 (8)
O1	0.126	0.126	0.126	0.000	0.059	0.000
O2	0.125	0.125	0.125	0.000	0.058	0.000
O3	0.060	0.060	0.060	0.000	0.028	0.000
O4	0.0303 (15)	0.0592 (18)	0.104 (3)	0.0045 (14)	0.0243 (17)	0.0019 (18)
O5	0.0352 (18)	0.081 (2)	0.139 (3)	−0.0110 (16)	0.019 (2)	0.033 (2)
N1	0.045 (2)	0.066 (3)	0.079 (3)	−0.0122 (19)	0.026 (2)	−0.003 (2)
N2	0.0366 (19)	0.051 (2)	0.047 (2)	0.0039 (17)	0.0183 (17)	0.0049 (17)
N3	0.0237 (17)	0.054 (2)	0.063 (2)	0.0083 (15)	0.0174 (17)	0.0154 (18)
C1	0.108	0.108	0.108	0.000	0.050	0.000
C2	0.071 (3)	0.044 (2)	0.060 (3)	−0.011 (2)	0.031 (3)	−0.008 (2)
C3	0.082 (3)	0.039 (2)	0.064 (3)	−0.017 (2)	0.033 (3)	−0.010 (2)
C4	0.064 (3)	0.064 (3)	0.048 (3)	−0.016 (2)	0.019 (2)	−0.006 (2)
C5	0.045 (2)	0.054 (2)	0.039 (3)	−0.013 (2)	0.023 (2)	0.001 (2)
C6	0.049 (2)	0.049 (2)	0.054 (3)	−0.006 (2)	0.022 (2)	−0.007 (2)
C7	0.062 (3)	0.049 (2)	0.068 (3)	−0.005 (2)	0.019 (2)	0.002 (2)
C8	0.052 (3)	0.053 (3)	0.044 (3)	−0.005 (2)	0.029 (2)	0.001 (2)
C9	0.036 (2)	0.061 (3)	0.047 (3)	−0.011 (2)	0.024 (2)	−0.003 (2)
C10	0.041 (2)	0.063 (3)	0.032 (2)	0.0101 (19)	0.015 (2)	0.009 (2)
C11	0.039 (2)	0.072 (3)	0.067 (3)	0.013 (2)	0.021 (2)	0.009 (3)
C12	0.066 (3)	0.077 (3)	0.070 (4)	0.026 (2)	0.030 (3)	0.010 (3)
C13	0.065 (3)	0.056 (3)	0.069 (3)	0.022 (2)	0.025 (3)	0.020 (2)
C14	0.064 (3)	0.059 (3)	0.051 (3)	0.017 (2)	0.028 (2)	0.013 (2)
C15	0.044 (2)	0.054 (2)	0.034 (2)	0.0106 (19)	0.013 (2)	0.003 (2)
C16	0.043 (3)	0.056 (3)	0.054 (3)	−0.010 (2)	0.016 (2)	0.009 (2)
C17	0.043 (3)	0.042 (2)	0.056 (3)	−0.009 (2)	0.007 (2)	0.014 (2)
C18	0.032 (2)	0.043 (2)	0.046 (3)	−0.0009 (17)	0.0154 (19)	0.003 (2)
C19	0.039 (2)	0.057 (2)	0.044 (3)	0.0027 (19)	0.017 (2)	0.008 (2)
C20	0.049 (3)	0.074 (3)	0.065 (3)	0.008 (2)	0.018 (2)	0.014 (3)
C21	0.045 (3)	0.061 (3)	0.077 (3)	0.010 (2)	0.020 (3)	0.009 (3)
C22	0.062 (3)	0.060 (3)	0.075 (3)	0.001 (2)	0.038 (3)	−0.007 (3)
C23	0.044 (2)	0.062 (3)	0.049 (3)	−0.009 (2)	0.026 (2)	0.001 (2)
C24	0.065 (3)	0.108 (4)	0.060 (4)	0.013 (3)	0.018 (3)	−0.010 (3)
C25	0.073 (3)	0.070 (3)	0.069 (3)	0.000 (3)	0.045 (3)	0.002 (3)

Geometric parameters (Å, º) top

S—O1	1.379 (5)	C10—C11	1.407 (5)
S—O2	1.395 (4)	C10—C15	1.413 (5)
S—C2	1.754 (4)	C11—C12	1.392 (6)
S—C1	1.777 (5)	C11—H11A	0.9300
O3—C9	1.343 (4)	C12—C13	1.322 (6)
O3—N1	1.420 (4)	C12—H12A	0.9300
O4—C15	1.349 (4)	C13—C14	1.375 (5)
O4—C16	1.417 (4)	C13—H13A	0.9300
O5—C17	1.228 (4)	C14—C15	1.366 (5)
N1—C8	1.313 (5)	C14—H14A	0.9300
N2—C9	1.298 (4)	C16—C17	1.486 (5)
N2—C8	1.383 (5)	C16—H16A	0.9700
N3—C17	1.337 (4)	C16—H16B	0.9700
N3—C18	1.453 (4)	C18—C19	1.378 (5)
N3—H3A	0.8600	C18—C23	1.399 (5)
C1—H1C	0.9600	C19—C20	1.382 (5)
C1—H1D	0.9600	C19—C25	1.524 (5)
C1—H1E	0.9600	C20—C21	1.343 (6)
C2—C7	1.388 (5)	C20—H20A	0.9300
C2—C3	1.395 (6)	C21—C22	1.375 (6)
C3—C4	1.374 (6)	C21—H21A	0.9300
C3—H3B	0.9300	C22—C23	1.398 (5)
C4—C5	1.356 (5)	C22—H22A	0.9300
C4—H4A	0.9300	C23—C24	1.502 (6)
C5—C6	1.384 (5)	C24—H24A	0.9600
C5—C8	1.476 (5)	C24—H24B	0.9600
C6—C7	1.371 (5)	C24—H24C	0.9600
C6—H6A	0.9300	C25—H25A	0.9600
C7—H7A	0.9300	C25—H25B	0.9600
C9—C10	1.422 (5)	C25—H25C	0.9600

O1—S—O2	120.0 (3)	C13—C12—H12A	120.0
O1—S—C2	107.0 (2)	C11—C12—H12A	120.0
O2—S—C2	109.8 (2)	C12—C13—C14	121.2 (4)
O1—S—C1	108.6 (3)	C12—C13—H13A	119.4
O2—S—C1	106.3 (3)	C14—C13—H13A	119.4
C2—S—C1	104.0 (2)	C15—C14—C13	120.9 (4)
C9—O3—N1	108.2 (3)	C15—C14—H14A	119.5
C15—O4—C16	121.3 (3)	C13—C14—H14A	119.5
C8—N1—O3	102.4 (3)	O4—C15—C14	125.3 (4)
C9—N2—C8	104.5 (3)	O4—C15—C10	114.8 (3)
C17—N3—C18	122.6 (3)	C14—C15—C10	119.9 (4)
C17—N3—H3A	118.7	O4—C16—C17	109.4 (3)
C18—N3—H3A	118.7	O4—C16—H16A	109.8
S—C1—H1C	109.5	C17—C16—H16A	109.8
S—C1—H1D	109.5	O4—C16—H16B	109.8
H1C—C1—H1D	109.5	C17—C16—H16B	109.8
S—C1—H1E	109.5	H16A—C16—H16B	108.3
H1C—C1—H1E	109.5	O5—C17—N3	123.7 (4)
H1D—C1—H1E	109.5	O5—C17—C16	120.1 (3)
C7—C2—C3	119.7 (4)	N3—C17—C16	116.2 (3)
C7—C2—S	119.5 (3)	C19—C18—C23	123.0 (4)
C3—C2—S	120.8 (3)	C19—C18—N3	119.1 (4)
C4—C3—C2	120.1 (4)	C23—C18—N3	117.9 (4)
C4—C3—H3B	120.0	C18—C19—C20	116.0 (4)
C2—C3—H3B	120.0	C18—C19—C25	121.6 (4)
C5—C4—C3	119.8 (4)	C20—C19—C25	122.4 (4)
C5—C4—H4A	120.1	C21—C20—C19	124.7 (5)
C3—C4—H4A	120.1	C21—C20—H20A	117.7
C4—C5—C6	120.9 (4)	C19—C20—H20A	117.7
C4—C5—C8	121.1 (4)	C20—C21—C22	117.7 (4)
C6—C5—C8	118.0 (4)	C20—C21—H21A	121.2
C7—C6—C5	120.2 (4)	C22—C21—H21A	121.2
C7—C6—H6A	119.9	C21—C22—C23	122.3 (4)
C5—C6—H6A	119.9	C21—C22—H22A	118.8
C6—C7—C2	119.3 (4)	C23—C22—H22A	118.8
C6—C7—H7A	120.3	C22—C23—C18	116.2 (4)
C2—C7—H7A	120.3	C22—C23—C24	121.2 (4)
N1—C8—N2	113.8 (4)	C18—C23—C24	122.6 (4)
N1—C8—C5	122.3 (4)	C23—C24—H24A	109.5
N2—C8—C5	123.8 (4)	C23—C24—H24B	109.5
N2—C9—O3	111.1 (3)	H24A—C24—H24B	109.5
N2—C9—C10	132.4 (4)	C23—C24—H24C	109.5
O3—C9—C10	116.4 (4)	H24A—C24—H24C	109.5
C11—C10—C15	116.8 (4)	H24B—C24—H24C	109.5
C11—C10—C9	120.8 (4)	C19—C25—H25A	109.5
C15—C10—C9	122.3 (3)	C19—C25—H25B	109.5
C12—C11—C10	121.0 (4)	H25A—C25—H25B	109.5
C12—C11—H11A	119.5	C19—C25—H25C	109.5
C10—C11—H11A	119.5	H25A—C25—H25C	109.5
C13—C12—C11	119.9 (4)	H25B—C25—H25C	109.5

C9—O3—N1—C8	−2.3 (4)	C9—C10—C11—C12	176.9 (4)
O1—S—C2—C7	50.9 (4)	C10—C11—C12—C13	−1.7 (7)
O2—S—C2—C7	−177.3 (4)	C11—C12—C13—C14	4.4 (8)
C1—S—C2—C7	−63.9 (4)	C12—C13—C14—C15	−3.1 (7)
O1—S—C2—C3	−127.6 (4)	C16—O4—C15—C14	8.1 (6)
O2—S—C2—C3	4.2 (5)	C16—O4—C15—C10	−172.0 (4)
C1—S—C2—C3	117.6 (4)	C13—C14—C15—O4	178.8 (4)
C7—C2—C3—C4	0.5 (7)	C13—C14—C15—C10	−1.0 (6)
S—C2—C3—C4	179.0 (4)	C11—C10—C15—O4	−176.4 (4)
C2—C3—C4—C5	1.1 (7)	C9—C10—C15—O4	4.5 (6)
C3—C4—C5—C6	−1.2 (7)	C11—C10—C15—C14	3.5 (6)
C3—C4—C5—C8	179.4 (4)	C9—C10—C15—C14	−175.6 (4)
C4—C5—C6—C7	−0.2 (6)	C15—O4—C16—C17	163.9 (4)
C8—C5—C6—C7	179.2 (4)	C18—N3—C17—O5	2.2 (7)
C5—C6—C7—C2	1.7 (7)	C18—N3—C17—C16	−180.0 (4)
C3—C2—C7—C6	−1.8 (7)	O4—C16—C17—O5	170.2 (4)
S—C2—C7—C6	179.6 (4)	O4—C16—C17—N3	−7.7 (5)
O3—N1—C8—N2	0.9 (4)	C17—N3—C18—C19	86.6 (5)
O3—N1—C8—C5	178.2 (3)	C17—N3—C18—C23	−94.3 (5)
C9—N2—C8—N1	0.9 (5)	C23—C18—C19—C20	0.6 (6)
C9—N2—C8—C5	−176.4 (4)	N3—C18—C19—C20	179.7 (3)
C4—C5—C8—N1	9.5 (6)	C23—C18—C19—C25	−178.6 (4)
C6—C5—C8—N1	−169.9 (4)	N3—C18—C19—C25	0.4 (5)
C4—C5—C8—N2	−173.5 (4)	C18—C19—C20—C21	−1.6 (6)
C6—C5—C8—N2	7.1 (6)	C25—C19—C20—C21	177.7 (4)
C8—N2—C9—O3	−2.4 (4)	C19—C20—C21—C22	0.1 (7)
C8—N2—C9—C10	−179.3 (4)	C20—C21—C22—C23	2.5 (7)
N1—O3—C9—N2	3.1 (4)	C21—C22—C23—C18	−3.3 (6)
N1—O3—C9—C10	−179.5 (3)	C21—C22—C23—C24	177.7 (4)
N2—C9—C10—C11	−163.6 (4)	C19—C18—C23—C22	1.7 (6)
O3—C9—C10—C11	19.6 (6)	N3—C18—C23—C22	−177.4 (3)
N2—C9—C10—C15	15.4 (7)	C19—C18—C23—C24	−179.3 (4)
O3—C9—C10—C15	−161.4 (4)	N3—C18—C23—C24	1.6 (6)
C15—C10—C11—C12	−2.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.86	2.14	2.556 (5)	109
N3—H3A···N2	0.86	2.43	3.288 (5)	176
C3—H3B···O2	0.93	2.59	2.946 (7)	103
C6—H6A···N2	0.93	2.56	2.901 (5)	102
C14—H14A···O2ⁱ	0.93	2.54	3.429 (7)	160
C16—H16A···O2ⁱ	0.97	2.57	3.310 (6)	133
C25—H25A···N3	0.96	2.41	2.883 (6)	110

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃N₃O₅S
M_r	477.52
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	28.848 (6), 13.648 (3), 13.562 (3)
β (°)	117.58 (3)
V (Å³)	4733 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.979, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	4737, 4643, 3927
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.178, 0.97
No. of reflections	4643
No. of parameters	283
No. of restraints	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.39

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.86	2.14	2.556 (5)	109
N3—H3A···N2	0.86	2.43	3.288 (5)	176
C3—H3B···O2	0.93	2.59	2.946 (7)	103
C6—H6A···N2	0.93	2.56	2.901 (5)	102
C14—H14A···O2ⁱ	0.93	2.54	3.429 (7)	160
C16—H16A···O2ⁱ	0.97	2.57	3.310 (6)	133
C25—H25A···N3	0.96	2.41	2.883 (6)	110

Symmetry code: (i) x, y+1, z.

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