N-[4-Acetyl-5-(3-methoxy-phen-yl)-4,5-dihydro-1,3,4-thia-diazol-2-yl]acetamide.

The title compound, C(13)H(15)N(3)O(3)S, crystallizes with two mol-ecules in the asymmetric unit. The thia-diazole rings in both the mol-ecules adopt an envelope conformation. The crystal packing is stabilized by inter-molecular N-H⋯O and C-H⋯O inter-actions.

Related literature

For biological activities of thia­diazole derivatives, see: Balasubramanian et al. (2004 ▶); Li et al. (2001 ▶); Radwan et al. (2007 ▶); Supuran et al. (2001 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C13H15N3O3S

M = 293.34

Monoclinic,

a = 11.3790 (4) Å

b = 10.5993 (3) Å

c = 11.9596 (2) Å

β = 108.225 (2)°

V = 1370.08 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.930, T max = 0.962

16660 measured reflections

7595 independent reflections

5635 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.03

7595 reflections

367 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), with 3584 Friedel pairs

Flack parameter: 0.07 (7)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032108/bt2802sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032108/bt2802Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H15N3O3S	F(000) = 616
Mr = 293.34	Dx = 1.422 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5353 reflections
a = 11.3790 (4) Å	θ = 1.8–29.6°
b = 10.5993 (3) Å	µ = 0.25 mm−1
c = 11.9596 (2) Å	T = 293 K
β = 108.225 (2)°	Prism, colourless
V = 1370.08 (7) Å3	0.30 × 0.20 × 0.16 mm
Z = 4

Bruker Kappa-APEXII CCD diffractometer	7595 independent reflections
Radiation source: fine-focus sealed tube	5635 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω and φ scans	θmax = 29.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −15→15
Tmin = 0.930, Tmax = 0.962	k = −14→14
16660 measured reflections	l = −14→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.2666P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
7595 reflections	Δρmax = 0.33 e Å−3
367 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), with 3584 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (7)

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.

	x	y	z	Uiso*/Ueq
C1	0.5869 (2)	0.7772 (2)	0.4618 (2)	0.0397 (5)
C2	0.6405 (3)	0.8511 (3)	0.3955 (3)	0.0498 (8)
H2	0.6027	0.8595	0.3148	0.060*
C3	0.7499 (3)	0.9119 (3)	0.4499 (2)	0.0538 (7)
H3	0.7862	0.9615	0.4055	0.065*
C4	0.8069 (2)	0.9005 (3)	0.5697 (2)	0.0442 (6)
H4	0.8808	0.9428	0.6055	0.053*
C5	0.7547 (2)	0.8268 (2)	0.6360 (2)	0.0309 (5)
C6	0.64253 (18)	0.7665 (2)	0.5812 (2)	0.0350 (5)
H6	0.6051	0.7186	0.6258	0.042*
C7	0.8123 (2)	0.8112 (3)	0.7677 (2)	0.0324 (6)
H7	0.7546	0.8419	0.8076	0.039*
C8	0.9343 (2)	1.0017 (3)	0.8382 (2)	0.0363 (6)
C9	1.0571 (2)	1.0645 (3)	0.8708 (3)	0.0441 (7)
H9A	1.0464	1.1541	0.8742	0.066*
H9B	1.0969	1.0455	0.8129	0.066*
H9C	1.1074	1.0346	0.9464	0.066*
C10	1.0096 (2)	0.6892 (3)	0.8300 (2)	0.0315 (6)
C11	1.0879 (3)	0.4753 (3)	0.8707 (2)	0.0390 (6)
C12	1.1970 (3)	0.3942 (3)	0.8773 (3)	0.0569 (8)
H12A	1.1920	0.3658	0.7997	0.085*
H12B	1.1975	0.3226	0.9267	0.085*
H12C	1.2716	0.4420	0.9098	0.085*
C13	0.4198 (2)	0.6425 (3)	0.4616 (3)	0.0548 (7)
H13A	0.3971	0.6925	0.5186	0.082*
H13B	0.4748	0.5763	0.5011	0.082*
H13C	0.3468	0.6062	0.4074	0.082*
C14	0.8900 (2)	0.2827 (3)	0.5333 (2)	0.0431 (6)
C15	0.8399 (3)	0.3437 (3)	0.6089 (3)	0.0499 (8)
H15	0.8734	0.3319	0.6897	0.060*
C16	0.7400 (3)	0.4223 (3)	0.5648 (2)	0.0524 (7)
H16	0.7053	0.4623	0.6162	0.063*
C17	0.6906 (2)	0.4425 (2)	0.4454 (2)	0.0420 (6)
H17	0.6236	0.4967	0.4164	0.050*
C18	0.7410 (2)	0.3820 (3)	0.3691 (2)	0.0313 (5)
C19	0.84171 (19)	0.3018 (2)	0.4136 (2)	0.0365 (5)
H19	0.8764	0.2611	0.3626	0.044*
C20	0.6864 (2)	0.3966 (3)	0.2384 (2)	0.0316 (5)
H20	0.7459	0.3662	0.2005	0.038*
C21	0.5698 (2)	0.2018 (3)	0.1704 (2)	0.0352 (6)
C22	0.4489 (2)	0.1337 (3)	0.1313 (3)	0.0457 (7)
H22A	0.4280	0.1056	0.1990	0.069*
H22B	0.4554	0.0621	0.0844	0.069*
H22C	0.3857	0.1895	0.0855	0.069*
C23	0.4851 (2)	0.5119 (3)	0.1630 (2)	0.0307 (5)
C24	0.4060 (2)	0.7251 (3)	0.1174 (2)	0.0371 (6)
C25	0.2952 (2)	0.8055 (3)	0.1067 (3)	0.0520 (8)
H25A	0.2616	0.8347	0.0271	0.078*
H25B	0.3190	0.8766	0.1587	0.078*
H25C	0.2340	0.7569	0.1275	0.078*
C26	1.0400 (3)	0.1360 (3)	0.5113 (3)	0.0692 (9)
H26A	1.0753	0.1935	0.4686	0.104*
H26B	0.9772	0.0863	0.4568	0.104*
H26C	1.1035	0.0814	0.5586	0.104*
N1	0.92957 (17)	0.8777 (2)	0.81336 (18)	0.0319 (5)
N2	1.03611 (17)	0.8057 (2)	0.8278 (2)	0.0339 (5)
N3	1.10017 (18)	0.5994 (2)	0.8432 (2)	0.0383 (5)
H3A	1.1689	0.6224	0.8336	0.046*
N4	0.57049 (17)	0.3249 (2)	0.1927 (2)	0.0332 (5)
N5	0.46128 (17)	0.3956 (2)	0.16790 (19)	0.0330 (5)
N6	0.39184 (18)	0.6002 (2)	0.1401 (2)	0.0357 (5)
H6A	0.3199	0.5754	0.1399	0.043*
O1	0.47967 (16)	0.7197 (2)	0.39944 (16)	0.0550 (5)
O2	0.83930 (16)	1.0588 (2)	0.8297 (2)	0.0525 (5)
O3	0.99404 (17)	0.4378 (2)	0.88764 (19)	0.0514 (5)
O4	0.98715 (18)	0.2046 (2)	0.58456 (19)	0.0676 (6)
O5	0.66898 (16)	0.1464 (2)	0.18601 (19)	0.0513 (5)
O6	0.50089 (16)	0.7653 (2)	0.10697 (18)	0.0487 (5)
S1	0.85560 (5)	0.64828 (6)	0.81229 (6)	0.03785 (17)
S2	0.63984 (5)	0.55696 (6)	0.18841 (6)	0.03857 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0346 (10)	0.0384 (13)	0.0415 (13)	0.0002 (9)	0.0053 (10)	−0.0048 (10)
C2	0.0547 (16)	0.054 (2)	0.0347 (15)	−0.0045 (14)	0.0053 (13)	0.0004 (13)
C3	0.0597 (15)	0.0617 (19)	0.0407 (15)	−0.0191 (14)	0.0166 (12)	0.0057 (13)
C4	0.0404 (12)	0.0500 (15)	0.0426 (14)	−0.0140 (11)	0.0136 (11)	−0.0016 (12)
C5	0.0285 (10)	0.0297 (14)	0.0349 (13)	0.0004 (9)	0.0102 (10)	−0.0034 (11)
C6	0.0299 (9)	0.0337 (12)	0.0405 (12)	−0.0024 (8)	0.0099 (9)	−0.0001 (10)
C7	0.0236 (10)	0.0341 (14)	0.0378 (14)	−0.0022 (10)	0.0071 (10)	−0.0053 (12)
C8	0.0347 (12)	0.0371 (16)	0.0382 (15)	0.0007 (11)	0.0129 (11)	−0.0028 (12)
C9	0.0377 (12)	0.0392 (16)	0.0552 (18)	−0.0079 (13)	0.0142 (12)	−0.0115 (15)
C10	0.0253 (10)	0.0370 (16)	0.0324 (13)	−0.0024 (10)	0.0093 (9)	−0.0015 (11)
C11	0.0412 (13)	0.0371 (16)	0.0370 (15)	−0.0039 (12)	0.0096 (11)	−0.0004 (12)
C12	0.0521 (16)	0.0326 (16)	0.086 (2)	0.0014 (14)	0.0209 (16)	0.0069 (17)
C13	0.0384 (12)	0.0568 (17)	0.0667 (18)	−0.0103 (12)	0.0129 (12)	−0.0108 (15)
C14	0.0331 (10)	0.0456 (15)	0.0455 (14)	−0.0001 (10)	0.0048 (10)	0.0045 (11)
C15	0.0554 (16)	0.055 (2)	0.0351 (16)	−0.0062 (14)	0.0080 (13)	−0.0022 (13)
C16	0.0600 (15)	0.0552 (18)	0.0441 (15)	0.0019 (13)	0.0192 (13)	−0.0117 (13)
C17	0.0406 (11)	0.0386 (13)	0.0458 (14)	0.0050 (10)	0.0119 (11)	−0.0053 (11)
C18	0.0251 (10)	0.0291 (14)	0.0374 (14)	−0.0036 (9)	0.0066 (10)	−0.0007 (11)
C19	0.0301 (9)	0.0380 (12)	0.0417 (13)	0.0036 (9)	0.0118 (9)	0.0018 (11)
C20	0.0237 (10)	0.0339 (14)	0.0383 (14)	−0.0015 (10)	0.0112 (10)	−0.0012 (12)
C21	0.0325 (12)	0.0351 (15)	0.0398 (15)	−0.0032 (11)	0.0141 (10)	−0.0071 (12)
C22	0.0401 (13)	0.0432 (18)	0.0551 (18)	−0.0099 (13)	0.0167 (12)	−0.0118 (15)
C23	0.0268 (10)	0.0343 (15)	0.0289 (13)	−0.0005 (10)	0.0056 (9)	0.0035 (10)
C24	0.0371 (13)	0.0330 (15)	0.0358 (14)	−0.0013 (11)	0.0036 (11)	0.0008 (12)
C25	0.0428 (14)	0.0347 (16)	0.074 (2)	0.0065 (12)	0.0111 (14)	0.0046 (16)
C26	0.0557 (16)	0.066 (2)	0.088 (2)	0.0258 (16)	0.0253 (16)	0.0328 (19)
N1	0.0219 (9)	0.0343 (13)	0.0381 (12)	−0.0010 (8)	0.0074 (8)	−0.0054 (10)
N2	0.0238 (9)	0.0348 (13)	0.0425 (13)	0.0014 (9)	0.0096 (9)	−0.0019 (10)
N3	0.0308 (10)	0.0327 (13)	0.0541 (14)	−0.0009 (8)	0.0171 (9)	0.0045 (10)
N4	0.0234 (9)	0.0334 (13)	0.0407 (13)	−0.0005 (9)	0.0069 (8)	−0.0048 (10)
N5	0.0257 (9)	0.0332 (13)	0.0388 (12)	0.0007 (9)	0.0083 (8)	−0.0038 (10)
N6	0.0272 (9)	0.0322 (13)	0.0461 (12)	−0.0002 (8)	0.0089 (8)	0.0034 (10)
O1	0.0433 (9)	0.0665 (13)	0.0459 (10)	−0.0145 (9)	0.0006 (8)	−0.0070 (10)
O2	0.0383 (9)	0.0388 (12)	0.0845 (15)	0.0039 (10)	0.0252 (10)	−0.0079 (12)
O3	0.0465 (11)	0.0472 (14)	0.0617 (13)	−0.0102 (10)	0.0187 (10)	0.0077 (11)
O4	0.0572 (11)	0.0840 (16)	0.0567 (12)	0.0303 (11)	0.0110 (10)	0.0231 (12)
O5	0.0363 (9)	0.0405 (12)	0.0795 (14)	0.0048 (10)	0.0216 (9)	−0.0079 (12)
O6	0.0431 (10)	0.0430 (13)	0.0617 (13)	−0.0049 (9)	0.0187 (9)	0.0097 (11)
S1	0.0281 (3)	0.0403 (4)	0.0434 (4)	−0.0051 (3)	0.0087 (2)	0.0057 (3)
S2	0.0264 (3)	0.0371 (4)	0.0505 (4)	−0.0023 (3)	0.0096 (3)	0.0090 (3)

C1—O1	1.359 (3)	C14—C19	1.377 (3)
C1—C6	1.374 (3)	C15—C16	1.374 (4)
C1—C2	1.384 (4)	C15—H15	0.9300
C2—C3	1.372 (4)	C16—C17	1.378 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.380 (4)	C17—C18	1.378 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.374 (3)	C18—C19	1.392 (3)
C4—H4	0.9300	C18—C20	1.499 (3)
C5—C6	1.394 (3)	C19—H19	0.9300
C5—C7	1.514 (4)	C20—N4	1.471 (3)
C6—H6	0.9300	C20—S2	1.824 (3)
C7—N1	1.456 (3)	C20—H20	0.9800
C7—S1	1.829 (3)	C21—O5	1.234 (3)
C7—H7	0.9800	C21—N4	1.332 (4)
C8—O2	1.215 (3)	C21—C22	1.493 (3)
C8—N1	1.345 (4)	C22—H22A	0.9600
C8—C9	1.486 (4)	C22—H22B	0.9600
C9—H9A	0.9600	C22—H22C	0.9600
C9—H9B	0.9600	C23—N5	1.267 (4)
C9—H9C	0.9600	C23—N6	1.377 (3)
C10—N2	1.274 (3)	C23—S2	1.757 (2)
C10—N3	1.375 (3)	C24—N6	1.370 (4)
C10—S1	1.753 (2)	C24—C25	1.493 (4)
C11—O3	1.215 (3)	C25—H25A	0.9600
C11—N3	1.373 (4)	C25—H25B	0.9600
C11—C12	1.492 (4)	C25—H25C	0.9600
C12—H12A	0.9600	C26—O4	1.410 (4)
C12—H12B	0.9600	C26—H26A	0.9600
C12—H12C	0.9600	C26—H26B	0.9600
C13—O1	1.416 (3)	C26—H26C	0.9600
C13—H13A	0.9600	N1—N2	1.397 (3)
C13—H13B	0.9600	N3—H3A	0.8600
C13—H13C	0.9600	N4—N5	1.401 (3)
C14—O4	1.364 (3)	N6—H6A	0.8600
C14—C15	1.373 (4)
O1—C1—C6	125.1 (2)	C16—C17—C18	119.6 (2)
O1—C1—C2	114.9 (2)	C16—C17—H17	120.2
C6—C1—C2	120.0 (2)	C18—C17—H17	120.2
C3—C2—C1	119.4 (3)	C17—C18—C19	119.6 (2)
C3—C2—H2	120.3	C17—C18—C20	121.3 (2)
C1—C2—H2	120.3	C19—C18—C20	119.0 (2)
C2—C3—C4	120.9 (3)	C14—C19—C18	120.0 (2)
C2—C3—H3	119.6	C14—C19—H19	120.0
C4—C3—H3	119.6	C18—C19—H19	120.0
C5—C4—C3	120.1 (2)	N4—C20—C18	111.4 (2)
C5—C4—H4	120.0	N4—C20—S2	103.01 (16)
C3—C4—H4	120.0	C18—C20—S2	114.9 (2)
C4—C5—C6	119.2 (2)	N4—C20—H20	109.1
C4—C5—C7	122.5 (2)	C18—C20—H20	109.1
C6—C5—C7	118.3 (2)	S2—C20—H20	109.1
C1—C6—C5	120.5 (2)	O5—C21—N4	119.2 (2)
C1—C6—H6	119.8	O5—C21—C22	121.8 (3)
C5—C6—H6	119.8	N4—C21—C22	118.9 (2)
N1—C7—C5	112.6 (2)	C21—C22—H22A	109.5
N1—C7—S1	102.46 (16)	C21—C22—H22B	109.5
C5—C7—S1	113.33 (19)	H22A—C22—H22B	109.5
N1—C7—H7	109.4	C21—C22—H22C	109.5
C5—C7—H7	109.4	H22A—C22—H22C	109.5
S1—C7—H7	109.4	H22B—C22—H22C	109.5
O2—C8—N1	119.7 (3)	N5—C23—N6	120.6 (2)
O2—C8—C9	122.5 (3)	N5—C23—S2	118.25 (19)
N1—C8—C9	117.7 (2)	N6—C23—S2	121.2 (2)
C8—C9—H9A	109.5	O6—C24—N6	121.8 (3)
C8—C9—H9B	109.5	O6—C24—C25	123.3 (3)
H9A—C9—H9B	109.5	N6—C24—C25	114.9 (2)
C8—C9—H9C	109.5	C24—C25—H25A	109.5
H9A—C9—H9C	109.5	C24—C25—H25B	109.5
H9B—C9—H9C	109.5	H25A—C25—H25B	109.5
N2—C10—N3	120.0 (2)	C24—C25—H25C	109.5
N2—C10—S1	118.12 (19)	H25A—C25—H25C	109.5
N3—C10—S1	121.8 (2)	H25B—C25—H25C	109.5
O3—C11—N3	120.9 (3)	O4—C26—H26A	109.5
O3—C11—C12	124.3 (3)	O4—C26—H26B	109.5
N3—C11—C12	114.8 (3)	H26A—C26—H26B	109.5
C11—C12—H12A	109.5	O4—C26—H26C	109.5
C11—C12—H12B	109.5	H26A—C26—H26C	109.5
H12A—C12—H12B	109.5	H26B—C26—H26C	109.5
C11—C12—H12C	109.5	C8—N1—N2	122.2 (2)
H12A—C12—H12C	109.5	C8—N1—C7	121.6 (2)
H12B—C12—H12C	109.5	N2—N1—C7	116.1 (2)
O1—C13—H13A	109.5	C10—N2—N1	109.3 (2)
O1—C13—H13B	109.5	C11—N3—C10	124.2 (2)
H13A—C13—H13B	109.5	C11—N3—H3A	117.9
O1—C13—H13C	109.5	C10—N3—H3A	117.9
H13A—C13—H13C	109.5	C21—N4—N5	122.2 (2)
H13B—C13—H13C	109.5	C21—N4—C20	122.0 (2)
O4—C14—C15	115.8 (2)	N5—N4—C20	115.8 (2)
O4—C14—C19	124.1 (2)	C23—N5—N4	110.0 (2)
C15—C14—C19	120.2 (2)	C24—N6—C23	124.4 (2)
C14—C15—C16	119.7 (3)	C24—N6—H6A	117.8
C14—C15—H15	120.1	C23—N6—H6A	117.8
C16—C15—H15	120.1	C1—O1—C13	117.9 (2)
C15—C16—C17	120.9 (3)	C14—O4—C26	118.5 (2)
C15—C16—H16	119.6	C10—S1—C7	88.3 (1)
C17—C16—H16	119.6	C23—S2—C20	88.6 (1)
O1—C1—C2—C3	−179.1 (3)	N3—C10—N2—N1	179.8 (2)
C6—C1—C2—C3	0.8 (4)	S1—C10—N2—N1	1.3 (3)
C1—C2—C3—C4	−0.1 (5)	C8—N1—N2—C10	162.3 (3)
C2—C3—C4—C5	0.5 (5)	C7—N1—N2—C10	−18.8 (3)
C3—C4—C5—C6	−1.4 (4)	O3—C11—N3—C10	−1.5 (4)
C3—C4—C5—C7	−179.6 (3)	C12—C11—N3—C10	178.4 (3)
O1—C1—C6—C5	178.2 (2)	N2—C10—N3—C11	166.0 (3)
C2—C1—C6—C5	−1.8 (4)	S1—C10—N3—C11	−15.5 (4)
C4—C5—C6—C1	2.1 (4)	O5—C21—N4—N5	174.7 (2)
C7—C5—C6—C1	−179.6 (2)	C22—C21—N4—N5	−7.5 (4)
C4—C5—C7—N1	−2.5 (4)	O5—C21—N4—C20	−1.6 (4)
C6—C5—C7—N1	179.3 (2)	C22—C21—N4—C20	176.2 (2)
C4—C5—C7—S1	−118.2 (2)	C18—C20—N4—C21	−81.9 (3)
C6—C5—C7—S1	63.5 (3)	S2—C20—N4—C21	154.4 (2)
O4—C14—C15—C16	−178.6 (3)	C18—C20—N4—N5	101.6 (3)
C19—C14—C15—C16	1.1 (4)	S2—C20—N4—N5	−22.2 (3)
C14—C15—C16—C17	−1.1 (5)	N6—C23—N5—N4	−179.8 (2)
C15—C16—C17—C18	0.8 (4)	S2—C23—N5—N4	−0.8 (3)
C16—C17—C18—C19	−0.4 (4)	C21—N4—N5—C23	−160.5 (3)
C16—C17—C18—C20	177.1 (3)	C20—N4—N5—C23	16.0 (3)
O4—C14—C19—C18	179.0 (2)	O6—C24—N6—C23	5.9 (4)
C15—C14—C19—C18	−0.7 (4)	C25—C24—N6—C23	−174.3 (2)
C17—C18—C19—C14	0.4 (4)	N5—C23—N6—C24	−170.8 (3)
C20—C18—C19—C14	−177.2 (2)	S2—C23—N6—C24	10.3 (4)
C17—C18—C20—N4	−74.4 (3)	C6—C1—O1—C13	0.0 (4)
C19—C18—C20—N4	103.1 (2)	C2—C1—O1—C13	180.0 (2)
C17—C18—C20—S2	42.2 (3)	C15—C14—O4—C26	177.9 (3)
C19—C18—C20—S2	−140.2 (2)	C19—C14—O4—C26	−1.8 (4)
O2—C8—N1—N2	−176.4 (2)	N2—C10—S1—C7	11.6 (2)
C9—C8—N1—N2	6.0 (4)	N3—C10—S1—C7	−166.9 (2)
O2—C8—N1—C7	4.7 (4)	N1—C7—S1—C10	−18.96 (18)
C9—C8—N1—C7	−172.9 (2)	C5—C7—S1—C10	102.70 (18)
C5—C7—N1—C8	82.3 (3)	N5—C23—S2—C20	−10.6 (2)
S1—C7—N1—C8	−155.5 (2)	N6—C23—S2—C20	168.4 (2)
C5—C7—N1—N2	−96.6 (3)	N4—C20—S2—C23	16.77 (18)
S1—C7—N1—N2	25.5 (3)	C18—C20—S2—C23	−104.62 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5i	0.86	1.95	2.801 (3)	171
N6—H6A···O2ii	0.86	1.96	2.799 (3)	164
C25—H25C···O2ii	0.96	2.37	3.238 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O5i	0.86	1.95	2.801 (3)	171
N6—H6A⋯O2ii	0.86	1.96	2.799 (3)	164
C25—H25C⋯O2ii	0.96	2.37	3.238 (4)	150

Symmetry codes: (i) ; (ii) .