Dimethyl (2Z)-2-[4-((1Z)-1-{2-[(2Z,5Z)-5-(2-meth-oxy-2-oxo-ethyl-idene)-4-oxo-3-phenyl-1,3-thia-zolidin-2-yl-idene]hydra-zin-1-yl-idene}eth-yl)anilino]but-2-ene-dio-ate.

The mol-ecule of the title compound, C26H24N4O7S, adopts a trans conformation about the central N-N bond, presumably to minimize steric between the substituents on these two atoms. An intra-molecular N-H⋯O hydrogen bond occurs. The phenyl ring is disordered over two sets of sites, with an occupancy ratio of 0.624 (8):0.376 (8). The azolidine ring is essentially planar [maximum deviation = 0.008 (5) Å] and makes a dihedral angle of 4.3 (2)° with the benzene ring and dihedral angles of 74.1 (3) and 69.1 (5)°, respectively, with the mean planes of the major and minor components of the disordered phenyl ring. The packing in the crystal is aided by the formation of several weak C-H⋯O and C-H⋯N inter-actions.

Related literature

For the biological activity of thia­zolidinene-containing compounds, see: Chaudhari et al. (1975 ▶); Chaudhary et al. (1976 ▶); Babaoglu et al. (2003 ▶); Dwivedi et al. (1972 ▶); Parmar et al. (1972 ▶); Bondock et al. (2007 ▶); Vicini et al. (2008 ▶); Gududuru et al. (2004 ▶); Ottanà et al. (2005 ▶); Agrawal et al. (2000 ▶); Diurno et al. (1999 ▶); Omar et al. (2010 ▶); Vigorita et al. (2003 ▶); Rawal et al. (2005 ▶); Suzuki et al. (1999 ▶).

Experimental

Crystal data

C26H24N4O7S

M = 536.56

Monoclinic,

a = 15.7027 (6) Å

b = 4.8543 (2) Å

c = 33.5974 (13) Å

β = 92.539 (3)°

V = 2558.47 (17) Å3

Z = 4

Cu Kα radiation

μ = 1.59 mm−1

T = 100 K

0.16 × 0.03 × 0.03 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.83, T max = 0.95

11600 measured reflections

3655 independent reflections

2351 reflections with I > 2σ(I)

R int = 0.106

θmax = 59.1°

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.156

S = 1.03

3655 reflections

339 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032042/sj5373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032042/sj5373Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813032042/sj5373Isup3.cml

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

C26H24N4O7S	F(000) = 1120
Mr = 536.56	Dx = 1.393 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 9855 reflections
a = 15.7027 (6) Å	θ = 3.1–61.2°
b = 4.8543 (2) Å	µ = 1.59 mm−1
c = 33.5974 (13) Å	T = 100 K
β = 92.539 (3)°	Column, yellow
V = 2558.47 (17) Å3	0.16 × 0.03 × 0.03 mm
Z = 4

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3655 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2351 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.106
Detector resolution: 10.4167 pixels mm-1	θmax = 59.1°, θmin = 2.6°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −5→5
Tmin = 0.83, Tmax = 0.95	l = −37→31
11600 measured reflections

Refinement on F2	6 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070	H-atom parameters constrained
wR(F2) = 0.156	W = 1/[Σ2(Fo2) + (0.0309P)2 + 6.4905P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3655 reflections	Δρmax = 0.30 e Å−3
339 parameters	Δρmin = −0.28 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
S1	0.82910 (8)	0.9838 (3)	0.07318 (4)	0.0352 (4)
O1	0.7365 (2)	1.5472 (9)	−0.02761 (10)	0.0509 (14)
O2	0.7018 (2)	1.2215 (9)	0.01654 (11)	0.0503 (14)
O3	1.0163 (2)	1.4497 (8)	0.04611 (11)	0.0500 (14)
O4	0.4439 (2)	−0.0248 (8)	0.10592 (10)	0.0485 (14)
O5	0.5638 (2)	−0.2773 (7)	0.10342 (10)	0.0383 (12)
O6	0.4864 (2)	−0.5316 (7)	0.24001 (10)	0.0420 (12)
O7	0.3549 (2)	−0.6713 (8)	0.22011 (10)	0.0474 (14)
N1	0.9907 (2)	1.0985 (9)	0.08935 (12)	0.0346 (14)
N2	0.9367 (3)	0.7543 (9)	0.12948 (12)	0.0370 (16)
N3	0.8626 (3)	0.5940 (8)	0.13394 (13)	0.0353 (14)
N4	0.5687 (2)	−0.2105 (8)	0.18830 (12)	0.0331 (14)
C1	0.6494 (4)	1.5545 (15)	−0.04284 (18)	0.066 (3)
C2	0.7544 (3)	1.3729 (12)	0.00233 (15)	0.0383 (17)
C3	0.8436 (3)	1.3888 (11)	0.01578 (15)	0.0372 (17)
C4	0.8772 (3)	1.2395 (11)	0.04549 (15)	0.0338 (17)
C5	0.9686 (3)	1.2793 (12)	0.05910 (15)	0.0382 (17)
C6	0.9255 (3)	0.9273 (11)	0.10114 (15)	0.0366 (17)
C7B	1.0773 (3)	1.0893 (13)	0.1080 (2)	0.0320 (17)	0.624 (8)
C8B	1.1061 (4)	1.2977 (13)	0.1336 (2)	0.044 (3)	0.624 (8)
C9B	1.1888 (4)	1.2897 (13)	0.1501 (2)	0.046 (3)	0.624 (8)
C10B	1.2426 (3)	1.0733 (14)	0.1411 (2)	0.045 (2)	0.624 (8)
C11B	1.2137 (4)	0.8649 (12)	0.1155 (2)	0.051 (3)	0.624 (8)
C12B	1.1311 (4)	0.8729 (12)	0.0990 (2)	0.045 (3)	0.624 (8)
C13	0.8620 (3)	0.4521 (10)	0.16606 (14)	0.0300 (17)
C14	0.9306 (3)	0.4598 (11)	0.19870 (15)	0.0426 (17)
C15	0.7858 (3)	0.2779 (10)	0.17131 (13)	0.0287 (17)
C16	0.7861 (3)	0.0648 (10)	0.19881 (14)	0.0312 (17)
C17	0.7147 (3)	−0.0942 (10)	0.20385 (14)	0.0327 (17)
C18	0.6403 (3)	−0.0423 (10)	0.18172 (14)	0.0300 (17)
C19	0.6384 (3)	0.1794 (10)	0.15518 (14)	0.0336 (17)
C20	0.7097 (3)	0.3316 (10)	0.14958 (14)	0.0317 (17)
C21	0.4985 (3)	−0.2571 (10)	0.16418 (14)	0.0324 (17)
C22	0.4970 (3)	−0.1693 (11)	0.12144 (15)	0.0354 (17)
C23	0.5758 (4)	−0.1888 (14)	0.06307 (15)	0.055 (2)
C24	0.4309 (3)	−0.4101 (10)	0.17585 (15)	0.0345 (17)
C25	0.4288 (3)	−0.5354 (11)	0.21454 (16)	0.0364 (17)
C26	0.3515 (4)	−0.8178 (14)	0.25707 (17)	0.058 (2)
C12A	1.0914 (6)	1.165 (3)	0.1430 (3)	0.045 (3)	0.376 (8)
C9A	1.2206 (5)	0.972 (3)	0.0964 (3)	0.046 (3)	0.376 (8)
C7A	1.0723 (5)	1.075 (2)	0.1044 (3)	0.0320 (17)	0.376 (8)
C8A	1.1370 (6)	0.978 (3)	0.0811 (3)	0.044 (3)	0.376 (8)
C10A	1.2397 (5)	1.063 (3)	0.1350 (3)	0.045 (2)	0.376 (8)
C11A	1.1750 (7)	1.159 (3)	0.1583 (3)	0.051 (3)	0.376 (8)
H1B	0.64500	1.67420	−0.06630	0.0980*
H1A	0.63100	1.36790	−0.05030	0.0980*
H11B	1.25050	0.71690	0.10940	0.0610*	0.624 (8)
H1C	0.61300	1.62650	−0.02230	0.0980*
H3	0.87960	1.51280	0.00250	0.0450*
H4	0.56980	−0.29720	0.21130	0.0400*
H8B	1.06940	1.44570	0.13970	0.0530*	0.624 (8)
H9B	1.20860	1.43210	0.16760	0.0550*	0.624 (8)
H10B	1.29910	1.06780	0.15240	0.0540*	0.624 (8)
H19	0.58670	0.22460	0.14090	0.0400*
H20	0.70770	0.47660	0.13060	0.0380*
H23A	0.52380	−0.22530	0.04670	0.0830*
H23B	0.62350	−0.29000	0.05220	0.0830*
H23C	0.58810	0.00910	0.06280	0.0830*
H24	0.38350	−0.43460	0.15770	0.0410*
H26A	0.39650	−0.95760	0.25860	0.0870*
H26B	0.29580	−0.90740	0.25860	0.0870*
H26C	0.35980	−0.68840	0.27930	0.0870*
H12B	1.11130	0.73040	0.08150	0.0540*	0.624 (8)
H14A	0.94080	0.27310	0.20900	0.0640*
H14B	0.91260	0.57890	0.22030	0.0640*
H14C	0.98330	0.53230	0.18810	0.0640*
H16	0.83660	0.02780	0.21450	0.0370*
H17	0.71670	−0.24050	0.22270	0.0390*
H8A	1.12400	0.91620	0.05470	0.0530*	0.376 (8)
H9A	1.26480	0.90630	0.08050	0.0550*	0.376 (8)
H10A	1.29680	1.05890	0.14550	0.0540*	0.376 (8)
H11A	1.18800	1.22130	0.18470	0.0610*	0.376 (8)
H12A	1.04720	1.23120	0.15890	0.0540*	0.376 (8)

	U11	U22	U33	U12	U13	U23
S1	0.0316 (7)	0.0325 (7)	0.0414 (7)	−0.0036 (6)	−0.0005 (6)	0.0001 (6)
O1	0.045 (2)	0.059 (3)	0.048 (2)	0.007 (2)	−0.0057 (18)	0.011 (2)
O2	0.032 (2)	0.067 (3)	0.052 (2)	−0.008 (2)	0.0031 (18)	0.006 (2)
O3	0.042 (2)	0.058 (3)	0.050 (2)	−0.015 (2)	0.0031 (18)	0.009 (2)
O4	0.037 (2)	0.054 (3)	0.054 (2)	0.010 (2)	−0.0040 (18)	0.014 (2)
O5	0.032 (2)	0.042 (2)	0.041 (2)	0.0025 (18)	0.0033 (16)	−0.0009 (17)
O6	0.040 (2)	0.041 (2)	0.044 (2)	−0.0105 (19)	−0.0094 (18)	0.0036 (18)
O7	0.034 (2)	0.056 (3)	0.052 (2)	−0.0129 (19)	−0.0018 (18)	0.014 (2)
N1	0.025 (2)	0.039 (3)	0.040 (2)	−0.006 (2)	0.0037 (19)	0.000 (2)
N2	0.030 (2)	0.034 (3)	0.047 (3)	−0.001 (2)	0.003 (2)	−0.002 (2)
N3	0.029 (2)	0.028 (2)	0.049 (3)	−0.002 (2)	0.003 (2)	−0.001 (2)
N4	0.034 (3)	0.028 (2)	0.037 (2)	−0.004 (2)	−0.002 (2)	0.0022 (19)
C1	0.053 (4)	0.083 (5)	0.060 (4)	0.020 (4)	−0.011 (3)	0.008 (4)
C2	0.042 (3)	0.041 (3)	0.032 (3)	0.003 (3)	0.004 (3)	−0.004 (3)
C3	0.035 (3)	0.039 (3)	0.038 (3)	−0.006 (3)	0.006 (3)	0.004 (3)
C4	0.025 (3)	0.036 (3)	0.041 (3)	−0.006 (2)	0.007 (2)	−0.004 (3)
C5	0.037 (3)	0.043 (3)	0.035 (3)	−0.005 (3)	0.005 (2)	0.000 (3)
C6	0.037 (3)	0.035 (3)	0.038 (3)	−0.002 (3)	0.004 (2)	−0.002 (3)
C7B	0.021 (3)	0.033 (3)	0.042 (3)	−0.004 (2)	0.002 (2)	−0.005 (3)
C8B	0.037 (5)	0.047 (5)	0.048 (5)	0.005 (4)	0.002 (4)	−0.009 (5)
C9B	0.037 (5)	0.056 (6)	0.045 (5)	0.007 (5)	−0.003 (4)	−0.018 (5)
C10B	0.024 (3)	0.051 (4)	0.059 (4)	0.002 (3)	−0.008 (3)	−0.007 (3)
C11B	0.028 (5)	0.063 (7)	0.062 (6)	0.008 (5)	−0.002 (4)	−0.026 (5)
C12B	0.023 (5)	0.054 (6)	0.058 (6)	−0.001 (4)	−0.004 (4)	−0.015 (5)
C13	0.026 (3)	0.022 (3)	0.042 (3)	0.006 (2)	0.001 (2)	−0.002 (2)
C14	0.034 (3)	0.037 (3)	0.056 (3)	−0.001 (3)	−0.008 (3)	0.010 (3)
C15	0.027 (3)	0.025 (3)	0.034 (3)	−0.001 (2)	0.000 (2)	−0.005 (2)
C16	0.028 (3)	0.025 (3)	0.040 (3)	0.001 (2)	−0.004 (2)	−0.002 (2)
C17	0.040 (3)	0.024 (3)	0.034 (3)	0.002 (2)	−0.001 (2)	0.000 (2)
C18	0.028 (3)	0.024 (3)	0.038 (3)	−0.006 (2)	0.002 (2)	−0.006 (2)
C19	0.032 (3)	0.023 (3)	0.045 (3)	0.004 (2)	−0.007 (2)	0.000 (2)
C20	0.028 (3)	0.025 (3)	0.042 (3)	0.000 (2)	0.000 (2)	−0.004 (2)
C21	0.029 (3)	0.028 (3)	0.040 (3)	0.007 (2)	−0.002 (2)	−0.001 (2)
C22	0.029 (3)	0.031 (3)	0.046 (3)	0.000 (3)	−0.001 (3)	0.001 (3)
C23	0.049 (4)	0.075 (5)	0.042 (3)	0.009 (3)	0.009 (3)	0.006 (3)
C24	0.029 (3)	0.032 (3)	0.042 (3)	0.004 (2)	−0.004 (2)	0.002 (2)
C25	0.027 (3)	0.030 (3)	0.052 (3)	−0.002 (3)	−0.002 (3)	−0.002 (3)
C26	0.038 (4)	0.071 (4)	0.064 (4)	−0.019 (3)	0.000 (3)	0.021 (4)
C12A	0.023 (5)	0.054 (6)	0.058 (6)	−0.001 (4)	−0.004 (4)	−0.015 (5)
C9A	0.037 (5)	0.056 (6)	0.045 (5)	0.007 (5)	−0.003 (4)	−0.018 (5)
C7A	0.021 (3)	0.033 (3)	0.042 (3)	−0.004 (2)	0.002 (2)	−0.005 (3)
C8A	0.037 (5)	0.047 (5)	0.048 (5)	0.005 (4)	0.002 (4)	−0.009 (5)
C10A	0.024 (3)	0.051 (4)	0.059 (4)	0.002 (3)	−0.008 (3)	−0.007 (3)
C11A	0.028 (5)	0.063 (7)	0.062 (6)	0.008 (5)	−0.002 (4)	−0.026 (5)

S1—C4	1.743 (5)	C13—C14	1.503 (7)
S1—C6	1.767 (5)	C15—C20	1.397 (7)
O1—C1	1.439 (7)	C15—C16	1.387 (7)
O1—C2	1.335 (7)	C16—C17	1.378 (7)
O2—C2	1.219 (6)	C17—C18	1.380 (7)
O3—C5	1.210 (6)	C18—C19	1.397 (7)
O4—C22	1.192 (6)	C19—C20	1.361 (7)
O5—C22	1.341 (6)	C21—C22	1.497 (7)
O5—C23	1.442 (6)	C21—C24	1.367 (7)
O6—C25	1.217 (6)	C24—C25	1.437 (7)
O7—C25	1.355 (6)	C1—H1A	0.9800
O7—C26	1.434 (7)	C1—H1B	0.9800
N1—C5	1.376 (7)	C1—H1C	0.9800
N1—C6	1.390 (6)	C3—H3	0.9500
N1—C7B	1.473 (6)	C8A—H8A	0.9500
N1—C7A	1.361 (9)	C8B—H8B	0.9500
N2—N3	1.413 (6)	C9A—H9A	0.9500
N2—C6	1.276 (7)	C9B—H9B	0.9500
N3—C13	1.281 (6)	C10A—H10A	0.9500
N4—C18	1.415 (6)	C10B—H10B	0.9500
N4—C21	1.358 (6)	C11A—H11A	0.9500
N4—H4	0.8800	C11B—H11B	0.9500
C2—C3	1.455 (7)	C12A—H12A	0.9500
C3—C4	1.324 (7)	C12B—H12B	0.9500
C4—C5	1.499 (7)	C14—H14A	0.9800
C7A—C12A	1.389 (15)	C14—H14B	0.9800
C7A—C8A	1.392 (14)	C14—H14C	0.9800
C7B—C8B	1.390 (9)	C16—H16	0.9500
C7B—C12B	1.390 (8)	C17—H17	0.9500
C8A—C9A	1.389 (13)	C19—H19	0.9500
C8B—C9B	1.390 (9)	C20—H20	0.9500
C9A—C10A	1.390 (15)	C23—H23B	0.9800
C9B—C10B	1.390 (9)	C23—H23C	0.9800
C10A—C11A	1.390 (15)	C23—H23A	0.9800
C10B—C11B	1.391 (9)	C24—H24	0.9500
C11A—C12A	1.389 (14)	C26—H26B	0.9800
C11B—C12B	1.388 (9)	C26—H26C	0.9800
C13—C15	1.482 (7)	C26—H26A	0.9800
C4—S1—C6	90.8 (2)	O4—C22—O5	125.4 (5)
C1—O1—C2	116.7 (4)	C21—C24—C25	122.6 (4)
C22—O5—C23	116.4 (4)	O6—C25—O7	121.6 (5)
C25—O7—C26	115.2 (4)	O6—C25—C24	125.7 (5)
C5—N1—C6	115.3 (4)	O7—C25—C24	112.7 (4)
C5—N1—C7B	122.1 (4)	O1—C1—H1A	109.00
C5—N1—C7A	122.0 (5)	O1—C1—H1B	109.00
C6—N1—C7B	122.6 (4)	O1—C1—H1C	109.00
C6—N1—C7A	122.5 (5)	H1A—C1—H1B	109.00
N3—N2—C6	110.8 (4)	H1A—C1—H1C	110.00
N2—N3—C13	115.0 (4)	H1B—C1—H1C	109.00
C18—N4—C21	129.2 (4)	C2—C3—H3	118.00
C21—N4—H4	115.00	C4—C3—H3	118.00
C18—N4—H4	115.00	C7A—C8A—H8A	120.00
O1—C2—C3	111.6 (4)	C9A—C8A—H8A	120.00
O2—C2—C3	124.8 (5)	C9B—C8B—H8B	120.00
O1—C2—O2	123.6 (4)	C7B—C8B—H8B	120.00
C2—C3—C4	123.5 (5)	C10A—C9A—H9A	120.00
S1—C4—C5	111.1 (4)	C8A—C9A—H9A	120.00
S1—C4—C3	128.6 (4)	C8B—C9B—H9B	120.00
C3—C4—C5	120.2 (5)	C10B—C9B—H9B	120.00
N1—C5—C4	110.5 (4)	C11A—C10A—H10A	120.00
O3—C5—C4	125.3 (5)	C9A—C10A—H10A	120.00
O3—C5—N1	124.2 (4)	C11B—C10B—H10B	120.00
S1—C6—N1	112.3 (4)	C9B—C10B—H10B	120.00
S1—C6—N2	125.8 (4)	C10A—C11A—H11A	120.00
N1—C6—N2	121.8 (4)	C12A—C11A—H11A	120.00
N1—C7A—C8A	121.2 (8)	C10B—C11B—H11B	120.00
C8A—C7A—C12A	119.9 (8)	C12B—C11B—H11B	120.00
N1—C7A—C12A	118.8 (8)	C7A—C12A—H12A	120.00
N1—C7B—C12B	119.3 (5)	C11A—C12A—H12A	120.00
C8B—C7B—C12B	120.0 (5)	C11B—C12B—H12B	120.00
N1—C7B—C8B	120.7 (5)	C7B—C12B—H12B	120.00
C7A—C8A—C9A	120.0 (10)	C13—C14—H14A	110.00
C7B—C8B—C9B	119.9 (6)	C13—C14—H14C	109.00
C8A—C9A—C10A	120.0 (9)	H14A—C14—H14B	109.00
C8B—C9B—C10B	120.0 (6)	C13—C14—H14B	110.00
C9A—C10A—C11A	119.9 (8)	H14B—C14—H14C	109.00
C9B—C10B—C11B	120.0 (5)	H14A—C14—H14C	109.00
C10A—C11A—C12A	120.1 (10)	C15—C16—H16	119.00
C10B—C11B—C12B	120.0 (5)	C17—C16—H16	119.00
C7A—C12A—C11A	120.0 (9)	C18—C17—H17	120.00
C7B—C12B—C11B	120.0 (6)	C16—C17—H17	120.00
N3—C13—C15	116.3 (4)	C18—C19—H19	120.00
C14—C13—C15	118.9 (4)	C20—C19—H19	120.00
N3—C13—C14	124.7 (4)	C15—C20—H20	119.00
C13—C15—C20	120.5 (4)	C19—C20—H20	119.00
C13—C15—C16	121.7 (4)	O5—C23—H23B	110.00
C16—C15—C20	117.7 (4)	O5—C23—H23C	110.00
C15—C16—C17	121.4 (4)	H23A—C23—H23C	109.00
C16—C17—C18	120.4 (4)	H23B—C23—H23C	110.00
C17—C18—C19	118.6 (4)	H23A—C23—H23B	109.00
N4—C18—C17	118.0 (4)	O5—C23—H23A	109.00
N4—C18—C19	123.3 (4)	C25—C24—H24	119.00
C18—C19—C20	120.8 (4)	C21—C24—H24	119.00
C15—C20—C19	121.1 (4)	O7—C26—H26C	109.00
N4—C21—C24	122.7 (4)	O7—C26—H26B	109.00
N4—C21—C22	120.2 (4)	H26B—C26—H26C	109.00
C22—C21—C24	116.8 (4)	H26A—C26—H26B	109.00
O5—C22—C21	110.0 (4)	H26A—C26—H26C	109.00
O4—C22—C21	124.6 (4)	O7—C26—H26A	110.00
C6—S1—C4—C3	178.8 (5)	S1—C4—C5—O3	−177.2 (5)
C6—S1—C4—C5	−0.7 (4)	C3—C4—C5—N1	−178.3 (5)
C4—S1—C6—N1	0.0 (4)	C3—C4—C5—O3	3.2 (8)
C4—S1—C6—N2	179.2 (5)	S1—C4—C5—N1	1.3 (5)
C1—O1—C2—C3	−178.6 (5)	N1—C7B—C12B—C11B	178.3 (5)
C1—O1—C2—O2	1.0 (8)	N1—C7B—C8B—C9B	−178.3 (6)
C23—O5—C22—C21	−174.0 (4)	C8B—C7B—C12B—C11B	−0.1 (10)
C23—O5—C22—O4	6.1 (7)	C12B—C7B—C8B—C9B	0.2 (10)
C26—O7—C25—C24	175.6 (5)	C7B—C8B—C9B—C10B	−0.2 (10)
C26—O7—C25—O6	−2.6 (7)	C8B—C9B—C10B—C11B	0.1 (10)
C5—N1—C6—N2	−178.4 (5)	C9B—C10B—C11B—C12B	−0.1 (10)
C7B—N1—C5—C4	179.1 (5)	C10B—C11B—C12B—C7B	0.1 (10)
C5—N1—C7B—C12B	−105.5 (7)	N3—C13—C15—C16	163.1 (5)
C6—N1—C5—O3	177.2 (5)	C14—C13—C15—C16	−19.2 (7)
C7B—N1—C5—O3	−2.4 (8)	C14—C13—C15—C20	158.1 (4)
C6—N1—C5—C4	−1.4 (6)	N3—C13—C15—C20	−19.5 (7)
C5—N1—C6—S1	0.8 (6)	C13—C15—C16—C17	179.2 (4)
C5—N1—C7B—C8B	72.9 (7)	C20—C15—C16—C17	1.8 (7)
C6—N1—C7B—C8B	−106.6 (7)	C16—C15—C20—C19	−0.1 (7)
C7B—N1—C6—N2	1.2 (8)	C13—C15—C20—C19	−177.6 (4)
C7B—N1—C6—S1	−179.6 (4)	C15—C16—C17—C18	−0.7 (7)
C6—N1—C7B—C12B	74.9 (7)	C16—C17—C18—C19	−2.0 (7)
N3—N2—C6—N1	−176.3 (4)	C16—C17—C18—N4	−179.5 (4)
N3—N2—C6—S1	4.6 (6)	C17—C18—C19—C20	3.7 (7)
C6—N2—N3—C13	−167.4 (5)	N4—C18—C19—C20	−179.0 (4)
N2—N3—C13—C15	−179.0 (4)	C18—C19—C20—C15	−2.6 (7)
N2—N3—C13—C14	3.5 (7)	C24—C21—C22—O4	61.8 (7)
C18—N4—C21—C24	−175.0 (5)	N4—C21—C22—O5	54.8 (6)
C21—N4—C18—C19	23.3 (8)	C22—C21—C24—C25	172.4 (5)
C18—N4—C21—C22	12.5 (7)	N4—C21—C22—O4	−125.3 (5)
C21—N4—C18—C17	−159.3 (5)	N4—C21—C24—C25	−0.3 (8)
O2—C2—C3—C4	−0.5 (9)	C24—C21—C22—O5	−118.2 (5)
O1—C2—C3—C4	179.1 (5)	C21—C24—C25—O7	178.4 (5)
C2—C3—C4—C5	−176.5 (5)	C21—C24—C25—O6	−3.5 (8)
C2—C3—C4—S1	4.0 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O6	0.88	2.01	2.705 (5)	135
C1—H1B···O4i	0.98	2.54	3.402 (8)	147
C3—H3···O3ii	0.95	2.37	3.191 (6)	145
C8B—H8B···N2iii	0.95	2.58	3.461 (8)	155
C12B—H12B···O3iv	0.95	2.31	3.216 (7)	159
C14—H14A···O6v	0.98	2.50	3.375 (6)	148
C14—H14C···N2	0.98	2.33	2.735 (7)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O6	0.88	2.01	2.705 (5)	135
C1—H1B⋯O4i	0.98	2.54	3.402 (8)	147
C3—H3⋯O3ii	0.95	2.37	3.191 (6)	145
C8B—H8B⋯N2iii	0.95	2.58	3.461 (8)	155
C12B—H12B⋯O3iv	0.95	2.31	3.216 (7)	159
C14—H14A⋯O6v	0.98	2.50	3.375 (6)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .