1,3-Bis(2-quinolylcarbon­yl)-1H,3H-2,1,3-benzothia­diazole 2-oxide

Jing, L.-H.

doi:10.1107/S1600536809033182

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2227

doi:10.1107/S1600536809033182

Open

access

1,3-Bis(2-quinolylcarbonyl)-1H,3H-2,1,3-benzothiadiazole 2-oxide

Lin-Hai Jing ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: jlhjhr@yahoo.com.cn

(Received 18 August 2009; accepted 20 August 2009; online 22 August 2009)

In the title compound, C₂₆H₁₆N₄O₃S, the thiadiazole ring adopts an envelope conformation, with the S atom occupying the flap position. The dihedral angle between the two quinoline ring systems is 55.32 (8)°. In the crystal, the molecules are linked into chains along [010] by C—H⋯O hydrogen bonds. The chains are connected via π–π interactions involving one of the pyridine rings [centroid–centroid distance = 3.5558 (18) Å].

Related literature

For benzothiadiazole derivatives as potential antidepressants, see: Pullar et al. (2000 ).

Experimental

Crystal data

C₂₆H₁₆N₄O₃S
M_r = 464.49
Triclinic, $[P \overline 1]$
a = 8.0914 (5) Å
b = 10.2920 (6) Å
c = 12.8843 (7) Å
α = 93.232 (2)°
β = 93.791 (2)°
γ = 101.746 (2)°
V = 1045.51 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 153 K
0.26 × 0.18 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: none
10347 measured reflections
4764 independent reflections
3074 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.189
S = 1.01
4764 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.51	3.262 (4)	136
Symmetry code: (i) x, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033182/ci2890sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033182/ci2890Isup2.hkl

checkCIF report

Comment top

Some of the benzothiadiazole derivatives are important and potential antidepressants (Pullar et al., 2000). Here, we report the crystal structure of the title compound (Fig.1).

Bond lengths and angles are normal. The N3- and N4-quinoline ring systems are planar, with maximum deviations of 0.022 (3) Å and 0.018 (3) Å, respectively, for atoms C16 and N4. The five-membered ring (N1/N2/C1/C6/S1) adopts an envelope conformation.

The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1) which link the molecules to form a chain along the b axis.

Related literature top

For benzothiadiazole derivatives as potential antidepressants, see: Pullar et al. (2000).

Experimental top

Quinoline-2-carboxylic acid (2 mmol) and an excess of thionyl chloride (6 mmol) were reacted at 333 K for 6 h. The solution was distilled under reduced pressure and a bright yellow solid was obtained. O-Phenylenediamine (1 mmol) in tetrahydrofuran (20 ml) was added to the bright yellow solid and reacted at 333 K for 6 h. Another excess of thionyl chloride (6 mmol) was added to the reaction system and the reaction was continued under reflux for 6 h.The reaction system was then cooled to ambient temperature and filtered to remove the tetrahydrofuran and unreacted thionyl chloride. The precipitate was dissolved in dimethylformamide and allowed to stand for one month at ambient temperature, after which time white single crystals of the title compound suitable for X-ray diffraction were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

1,3-Bis(2-quinolylcarbonyl)-1H,3H-2,1,3-benzothiadiazole 2-oxide top

Crystal data top

C₂₆H₁₆N₄O₃S	Z = 2
M_r = 464.49	F(000) = 480
Triclinic, P1	D_x = 1.475 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0914 (5) Å	Cell parameters from 6929 reflections
b = 10.2920 (6) Å	θ = 3.1–27.5°
c = 12.8843 (7) Å	µ = 0.20 mm⁻¹
α = 93.232 (2)°	T = 153 K
β = 93.791 (2)°	Block, white
γ = 101.746 (2)°	0.26 × 0.18 × 0.12 mm
V = 1045.51 (11) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3074 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.059
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −10→10
10347 measured reflections	k = −13→13
4764 independent reflections	l = −16→16

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1P)² + 0.398P] where P = (F_o² + 2F_c²)/3
4764 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₂₆H₁₆N₄O₃S	γ = 101.746 (2)°
M_r = 464.49	V = 1045.51 (11) Å³
Triclinic, P1	Z = 2
a = 8.0914 (5) Å	Mo Kα radiation
b = 10.2920 (6) Å	µ = 0.20 mm⁻¹
c = 12.8843 (7) Å	T = 153 K
α = 93.232 (2)°	0.26 × 0.18 × 0.12 mm
β = 93.791 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3074 reflections with I > 2σ(I)
10347 measured reflections	R_int = 0.059
4764 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
4764 reflections	Δρ_min = −0.66 e Å⁻³
307 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
S1	0.69178 (9)	0.31618 (7)	0.73387 (5)	0.0259 (2)
N1	0.6436 (3)	0.1832 (2)	0.81493 (19)	0.0270 (5)
N2	0.7768 (3)	0.2062 (2)	0.6523 (2)	0.0307 (6)
N3	0.4869 (3)	0.3845 (2)	0.86504 (18)	0.0247 (5)
N4	0.7299 (3)	0.4345 (2)	0.56732 (19)	0.0298 (6)
O1	0.8377 (2)	0.40615 (19)	0.78560 (15)	0.0294 (5)
O2	0.4360 (3)	0.0432 (2)	0.89052 (18)	0.0361 (5)
O3	0.8451 (3)	0.1354 (2)	0.49310 (17)	0.0419 (6)
C1	0.7478 (4)	0.0898 (3)	0.8014 (2)	0.0286 (6)
C2	0.7825 (4)	−0.0001 (3)	0.8718 (2)	0.0323 (7)
H2	0.7318	−0.0064	0.9362	0.039*
C3	0.8936 (4)	−0.0807 (3)	0.8452 (3)	0.0358 (7)
H3	0.9189	−0.1434	0.8919	0.043*
C4	0.9685 (4)	−0.0710 (3)	0.7510 (3)	0.0349 (7)
H4	1.0437	−0.1274	0.7342	0.042*
C5	0.9345 (4)	0.0204 (3)	0.6810 (2)	0.0340 (7)
H5	0.9867	0.0278	0.6171	0.041*
C6	0.8234 (4)	0.0996 (3)	0.7071 (2)	0.0292 (6)
C7	0.4910 (3)	0.1526 (3)	0.8607 (2)	0.0250 (6)
C8	0.3985 (3)	0.2634 (3)	0.8743 (2)	0.0254 (6)
C9	0.2277 (3)	0.2344 (3)	0.8967 (2)	0.0273 (6)
H9	0.1702	0.1455	0.9033	0.033*
C10	0.1467 (4)	0.3382 (3)	0.9088 (2)	0.0285 (6)
H10	0.0309	0.3219	0.9232	0.034*
C11	0.1604 (4)	0.5824 (3)	0.9083 (2)	0.0298 (6)
H11	0.0446	0.5719	0.9218	0.036*
C12	0.2545 (4)	0.7056 (3)	0.8968 (2)	0.0342 (7)
H12	0.2034	0.7807	0.9033	0.041*
C13	0.4257 (4)	0.7242 (3)	0.8756 (2)	0.0327 (7)
H13	0.4882	0.8111	0.8671	0.039*
C14	0.5021 (4)	0.6186 (3)	0.8672 (2)	0.0299 (6)
H14	0.6184	0.6318	0.8543	0.036*
C15	0.4078 (3)	0.4884 (3)	0.8777 (2)	0.0253 (6)
C16	0.2359 (4)	0.4696 (3)	0.8999 (2)	0.0267 (6)
C17	0.8056 (4)	0.2214 (3)	0.5479 (2)	0.0321 (7)
C18	0.7883 (4)	0.3522 (3)	0.5066 (2)	0.0291 (6)
C19	0.8409 (4)	0.3778 (3)	0.4052 (2)	0.0369 (7)
H19	0.8819	0.3140	0.3636	0.044*
C20	0.8294 (4)	0.5000 (4)	0.3707 (2)	0.0392 (8)
H20	0.8667	0.5233	0.3045	0.047*
C21	0.7451 (4)	0.7167 (3)	0.4011 (3)	0.0414 (8)
H21	0.7778	0.7432	0.3347	0.050*
C22	0.6821 (4)	0.8002 (3)	0.4645 (3)	0.0442 (9)
H22	0.6720	0.8850	0.4425	0.053*
C23	0.6310 (4)	0.7630 (3)	0.5634 (3)	0.0423 (8)
H23	0.5855	0.8223	0.6070	0.051*
C24	0.6469 (4)	0.6424 (3)	0.5963 (2)	0.0355 (7)
H24	0.6134	0.6179	0.6629	0.043*
C25	0.7126 (4)	0.5542 (3)	0.5320 (2)	0.0299 (6)
C26	0.7633 (4)	0.5896 (3)	0.4320 (2)	0.0344 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0268 (4)	0.0243 (4)	0.0281 (4)	0.0063 (3)	0.0061 (3)	0.0076 (3)
N1	0.0305 (13)	0.0221 (11)	0.0321 (12)	0.0105 (10)	0.0093 (10)	0.0068 (10)
N2	0.0303 (13)	0.0303 (13)	0.0349 (13)	0.0104 (11)	0.0086 (10)	0.0097 (11)
N3	0.0255 (12)	0.0234 (11)	0.0259 (11)	0.0055 (9)	0.0035 (9)	0.0060 (10)
N4	0.0307 (13)	0.0310 (13)	0.0278 (12)	0.0042 (11)	0.0046 (10)	0.0080 (11)
O1	0.0271 (10)	0.0271 (10)	0.0329 (11)	0.0024 (8)	0.0023 (8)	0.0043 (9)
O2	0.0350 (12)	0.0281 (11)	0.0502 (13)	0.0108 (9)	0.0157 (10)	0.0154 (10)
O3	0.0513 (15)	0.0421 (13)	0.0348 (12)	0.0150 (12)	0.0085 (10)	−0.0010 (11)
C1	0.0259 (14)	0.0245 (13)	0.0377 (16)	0.0083 (12)	0.0047 (12)	0.0066 (12)
C2	0.0326 (16)	0.0296 (15)	0.0371 (16)	0.0085 (13)	0.0073 (13)	0.0090 (13)
C3	0.0306 (16)	0.0295 (15)	0.0498 (19)	0.0100 (13)	0.0035 (14)	0.0105 (14)
C4	0.0290 (15)	0.0278 (15)	0.0503 (19)	0.0118 (13)	0.0043 (14)	0.0016 (14)
C5	0.0297 (16)	0.0356 (16)	0.0382 (16)	0.0093 (13)	0.0062 (13)	0.0026 (14)
C6	0.0277 (15)	0.0275 (14)	0.0345 (15)	0.0091 (12)	0.0053 (12)	0.0063 (13)
C7	0.0281 (14)	0.0216 (13)	0.0271 (13)	0.0076 (11)	0.0053 (11)	0.0045 (11)
C8	0.0264 (14)	0.0266 (14)	0.0242 (13)	0.0059 (11)	0.0031 (11)	0.0072 (12)
C9	0.0271 (14)	0.0262 (14)	0.0294 (14)	0.0051 (11)	0.0046 (11)	0.0075 (12)
C10	0.0251 (14)	0.0319 (15)	0.0294 (14)	0.0055 (12)	0.0057 (11)	0.0086 (12)
C11	0.0307 (15)	0.0294 (14)	0.0306 (14)	0.0102 (12)	0.0013 (12)	0.0006 (13)
C12	0.0387 (17)	0.0276 (15)	0.0387 (17)	0.0135 (13)	0.0001 (13)	0.0023 (13)
C13	0.0360 (16)	0.0255 (14)	0.0374 (16)	0.0078 (12)	0.0000 (13)	0.0071 (13)
C14	0.0299 (15)	0.0306 (15)	0.0286 (14)	0.0035 (12)	0.0014 (11)	0.0083 (13)
C15	0.0283 (14)	0.0266 (13)	0.0224 (13)	0.0075 (11)	0.0028 (11)	0.0065 (11)
C16	0.0287 (14)	0.0289 (14)	0.0238 (13)	0.0086 (12)	0.0026 (11)	0.0046 (12)
C17	0.0327 (16)	0.0346 (16)	0.0301 (15)	0.0079 (13)	0.0076 (12)	0.0031 (13)
C18	0.0268 (14)	0.0332 (15)	0.0250 (14)	0.0007 (12)	0.0018 (11)	0.0040 (13)
C19	0.0360 (17)	0.0472 (19)	0.0272 (15)	0.0071 (15)	0.0033 (13)	0.0041 (15)
C20	0.0341 (17)	0.055 (2)	0.0279 (15)	0.0038 (15)	0.0054 (13)	0.0157 (16)
C21	0.0404 (18)	0.0418 (18)	0.0382 (17)	−0.0024 (15)	−0.0037 (14)	0.0174 (16)
C22	0.0432 (19)	0.0295 (16)	0.055 (2)	−0.0025 (14)	−0.0107 (16)	0.0165 (17)
C23	0.0421 (19)	0.0340 (17)	0.051 (2)	0.0087 (15)	−0.0011 (15)	0.0038 (16)
C24	0.0359 (17)	0.0356 (16)	0.0342 (16)	0.0041 (14)	0.0030 (13)	0.0074 (14)
C25	0.0263 (14)	0.0319 (15)	0.0288 (14)	−0.0008 (12)	−0.0001 (11)	0.0075 (13)
C26	0.0283 (15)	0.0415 (17)	0.0300 (15)	−0.0020 (13)	−0.0010 (12)	0.0123 (14)

Geometric parameters (Å, º) top

S1—O1	1.441 (2)	C10—H10	0.95
S1—N1	1.764 (2)	C11—C12	1.361 (4)
S1—N2	1.771 (3)	C11—C16	1.420 (4)
N1—C7	1.390 (3)	C11—H11	0.95
N1—C1	1.413 (3)	C12—C13	1.407 (4)
N2—C17	1.393 (4)	C12—H12	0.95
N2—C6	1.437 (3)	C13—C14	1.359 (4)
N3—C8	1.321 (3)	C13—H13	0.95
N3—C15	1.361 (3)	C14—C15	1.419 (4)
N4—C18	1.300 (4)	C14—H14	0.95
N4—C25	1.368 (3)	C15—C16	1.416 (4)
O2—C7	1.217 (3)	C17—C18	1.504 (4)
O3—C17	1.208 (4)	C18—C19	1.422 (4)
C1—C2	1.388 (4)	C19—C20	1.376 (5)
C1—C6	1.396 (4)	C19—H19	0.95
C2—C3	1.388 (4)	C20—C26	1.391 (5)
C2—H2	0.95	C20—H20	0.95
C3—C4	1.391 (5)	C21—C22	1.349 (5)
C3—H3	0.95	C21—C26	1.422 (4)
C4—C5	1.393 (4)	C21—H21	0.95
C4—H4	0.95	C22—C23	1.415 (5)
C5—C6	1.376 (4)	C22—H22	0.95
C5—H5	0.95	C23—C24	1.362 (4)
C7—C8	1.495 (4)	C23—H23	0.95
C8—C9	1.406 (4)	C24—C25	1.400 (4)
C9—C10	1.369 (4)	C24—H24	0.95
C9—H9	0.95	C25—C26	1.422 (4)
C10—C16	1.412 (4)

O1—S1—N1	105.89 (12)	C11—C12—H12	119.3
O1—S1—N2	104.62 (12)	C13—C12—H12	119.3
N1—S1—N2	86.41 (10)	C14—C13—C12	120.4 (3)
C7—N1—C1	122.2 (2)	C14—C13—H13	119.8
C7—N1—S1	122.68 (17)	C12—C13—H13	119.8
C1—N1—S1	112.25 (17)	C13—C14—C15	119.8 (3)
C17—N2—C6	122.0 (3)	C13—C14—H14	120.1
C17—N2—S1	125.42 (19)	C15—C14—H14	120.1
C6—N2—S1	112.54 (19)	N3—C15—C16	121.9 (2)
C8—N3—C15	118.0 (2)	N3—C15—C14	118.2 (2)
C18—N4—C25	118.8 (2)	C16—C15—C14	119.9 (2)
C2—C1—C6	121.0 (3)	C10—C16—C15	117.9 (2)
C2—C1—N1	126.8 (3)	C10—C16—C11	123.4 (3)
C6—C1—N1	112.2 (2)	C15—C16—C11	118.7 (3)
C3—C2—C1	118.0 (3)	O3—C17—N2	122.2 (3)
C3—C2—H2	121.0	O3—C17—C18	121.2 (3)
C1—C2—H2	121.0	N2—C17—C18	116.6 (3)
C2—C3—C4	120.9 (3)	N4—C18—C19	125.0 (3)
C2—C3—H3	119.5	N4—C18—C17	117.4 (2)
C4—C3—H3	119.5	C19—C18—C17	117.6 (3)
C3—C4—C5	120.9 (3)	C20—C19—C18	116.5 (3)
C3—C4—H4	119.6	C20—C19—H19	121.8
C5—C4—H4	119.6	C18—C19—H19	121.8
C6—C5—C4	118.2 (3)	C19—C20—C26	120.4 (3)
C6—C5—H5	120.9	C19—C20—H20	119.8
C4—C5—H5	120.9	C26—C20—H20	119.8
C5—C6—C1	121.1 (2)	C22—C21—C26	121.0 (3)
C5—C6—N2	128.8 (3)	C22—C21—H21	119.5
C1—C6—N2	110.0 (2)	C26—C21—H21	119.5
O2—C7—N1	122.7 (2)	C21—C22—C23	120.8 (3)
O2—C7—C8	121.1 (2)	C21—C22—H22	119.6
N1—C7—C8	116.2 (2)	C23—C22—H22	119.6
N3—C8—C9	124.4 (2)	C24—C23—C22	120.1 (3)
N3—C8—C7	116.1 (2)	C24—C23—H23	120.0
C9—C8—C7	119.5 (2)	C22—C23—H23	120.0
C10—C9—C8	118.0 (2)	C23—C24—C25	120.2 (3)
C10—C9—H9	121.0	C23—C24—H24	119.9
C8—C9—H9	121.0	C25—C24—H24	119.9
C9—C10—C16	119.8 (2)	N4—C25—C24	119.1 (2)
C9—C10—H10	120.1	N4—C25—C26	120.4 (3)
C16—C10—H10	120.1	C24—C25—C26	120.4 (3)
C12—C11—C16	119.8 (3)	C20—C26—C21	123.6 (3)
C12—C11—H11	120.1	C20—C26—C25	118.9 (3)
C16—C11—H11	120.1	C21—C26—C25	117.5 (3)
C11—C12—C13	121.4 (3)

O1—S1—N1—C7	118.1 (2)	C12—C13—C14—C15	1.3 (5)
N2—S1—N1—C7	−137.7 (3)	C8—N3—C15—C16	−0.1 (4)
O1—S1—N1—C1	−80.7 (2)	C8—N3—C15—C14	−179.6 (3)
N2—S1—N1—C1	23.5 (2)	C13—C14—C15—N3	177.7 (3)
O1—S1—N2—C17	−93.9 (3)	C13—C14—C15—C16	−1.9 (4)
N1—S1—N2—C17	160.6 (3)	C9—C10—C16—C15	0.5 (4)
O1—S1—N2—C6	83.0 (2)	C9—C10—C16—C11	178.1 (3)
N1—S1—N2—C6	−22.5 (2)	N3—C15—C16—C10	0.0 (4)
C7—N1—C1—C2	−40.6 (5)	C14—C15—C16—C10	179.5 (3)
S1—N1—C1—C2	158.0 (3)	N3—C15—C16—C11	−177.7 (3)
C7—N1—C1—C6	142.0 (3)	C14—C15—C16—C11	1.8 (4)
S1—N1—C1—C6	−19.3 (3)	C12—C11—C16—C10	−178.8 (3)
C6—C1—C2—C3	−0.5 (5)	C12—C11—C16—C15	−1.2 (4)
N1—C1—C2—C3	−177.7 (3)	C6—N2—C17—O3	12.3 (5)
C1—C2—C3—C4	0.3 (5)	S1—N2—C17—O3	−171.1 (2)
C2—C3—C4—C5	0.3 (5)	C6—N2—C17—C18	−166.5 (3)
C3—C4—C5—C6	−0.8 (5)	S1—N2—C17—C18	10.1 (4)
C4—C5—C6—C1	0.6 (5)	C25—N4—C18—C19	1.7 (5)
C4—C5—C6—N2	175.4 (3)	C25—N4—C18—C17	−180.0 (3)
C2—C1—C6—C5	0.1 (5)	O3—C17—C18—N4	173.6 (3)
N1—C1—C6—C5	177.6 (3)	N2—C17—C18—N4	−7.6 (4)
C2—C1—C6—N2	−175.6 (3)	O3—C17—C18—C19	−7.8 (5)
N1—C1—C6—N2	1.9 (4)	N2—C17—C18—C19	171.0 (3)
C17—N2—C6—C5	18.0 (5)	N4—C18—C19—C20	0.6 (5)
S1—N2—C6—C5	−159.0 (3)	C17—C18—C19—C20	−177.8 (3)
C17—N2—C6—C1	−166.8 (3)	C18—C19—C20—C26	−2.2 (5)
S1—N2—C6—C1	16.2 (3)	C26—C21—C22—C23	−0.6 (5)
C1—N1—C7—O2	−1.1 (5)	C21—C22—C23—C24	0.8 (5)
S1—N1—C7—O2	158.3 (2)	C22—C23—C24—C25	−0.5 (5)
C1—N1—C7—C8	177.2 (3)	C18—N4—C25—C24	178.9 (3)
S1—N1—C7—C8	−23.4 (4)	C18—N4—C25—C26	−2.2 (4)
C15—N3—C8—C9	−0.2 (4)	C23—C24—C25—N4	179.0 (3)
C15—N3—C8—C7	−179.5 (2)	C23—C24—C25—C26	0.0 (5)
O2—C7—C8—N3	162.9 (3)	C19—C20—C26—C21	−179.1 (3)
N1—C7—C8—N3	−15.4 (4)	C19—C20—C26—C25	1.7 (5)
O2—C7—C8—C9	−16.4 (4)	C22—C21—C26—C20	−179.1 (3)
N1—C7—C8—C9	165.2 (3)	C22—C21—C26—C25	0.1 (5)
N3—C8—C9—C10	0.7 (4)	N4—C25—C26—C20	0.5 (5)
C7—C8—C9—C10	179.9 (3)	C24—C25—C26—C20	179.5 (3)
C8—C9—C10—C16	−0.8 (4)	N4—C25—C26—C21	−178.7 (3)
C16—C11—C12—C13	0.7 (5)	C24—C25—C26—C21	0.2 (4)
C11—C12—C13—C14	−0.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.51	3.262 (4)	136

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₆N₄O₃S
M_r	464.49
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	8.0914 (5), 10.2920 (6), 12.8843 (7)
α, β, γ (°)	93.232 (2), 93.791 (2), 101.746 (2)
V (Å³)	1045.51 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.26 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10347, 4764, 3074
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.189, 1.01
No. of reflections	4764
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.66

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.51	3.262 (4)	136

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

Acknowledgements

The authors thank the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

References

Pullar, I. A., Carney, S. L., Colvin, E. M., Lucaites, V. L., Nelson, D. L. & Wedley, S. (2000). Eur. J. Pharmacol. 407, 39–46. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar