2-[(E)-(4-Hydr­oxy-3-methoxy­benzyl­idene)amino]-N-(2-methyl­phen­yl)-4,5,6,7-tetra­hydro-1-benzothio­phene-3-carboxamide

The title compound, C₂₄H₂₄N₂O₃S, exhibits anti­fungal and anti­bacterial properties. The compound crystallizes with two mol­ecules in the asymmetric unit, with one mol­ecule exhibiting `orientational disorder' in the crystal structure with respect to the cyclo­hexene ring. The o-toluidine groups in both mol­ecules are noncoplanar with the respective cyclo­hexene-fused thio­phene ring. In both mol­ecules, there is an intra­molecular N—H...N hydrogen bond forming a pseudo-six-membered ring which locks the mol­ecular conformation and eliminates conformational flexibility. The crystal structure is stabilized by O—H...O hydrogen bonds; both mol­ecules in the asymmetric unit form independent chains, each such chain consisting of alternating `ordered' and `disordered' mol­ecules in the crystal lattice.

S1. Comment

The design of compounds possessing important pharmacological properties, such as antibacterial, anti-cancer, anti-inflammatory and antitoxic activities, is an important area of research. In this respect, Schiff bases (Pellis & West, 1968; Cohen et al.,1977; Csaszar & Morvay, 1983; Lakshmi et al., 1985) and their related thiophene derivatives (El-Maghraby et al., 1984; Dzhurayev et al., 1992; Gewald et al., 1966) have been synthesized and found to exhibit such biological activities. In this context, sulfur-containing Schiff bases are the most effective. In view of medicinal applications of such classes of compounds, single-crystal structure determinations on a series of biologically active thiophene-3-carboxamide derivatives have been performed (Vasu et al., 2003). In most of these structure determinations the molecular scaffold which remains invariant is the 2-[(E)-benzylideneamino]-N-phenyl-4,5,6,7-tetrahydro-1-benzothiophene- 3-carboxamide group. The molecular skeleton is divided into three parts, namely the cyclohexene fused thiophene group, the N-phenyl part and the benzylideneamino group. It was observed that the cyclohexene ring is ordered in all the above determined crystal structures. In one such structure determination, viz. 2-({(1E)-[4-(dimethylamino)phenyl]methylene}amino)-N-(4-methylphenyl)- 4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide (Vasu et al., 2003), the asymmetric unit contains two molecules·It is indeed noteworthy that in the title compound, although it crystallizes with two molecules (A and B) in asymmetric unit (Fig. 1), one molecule exhibits orientational disorder (molecule B) in the crystal lattice. The disorder could be well resolved, with the cyclohexene ring having two independent conformations, the major conformer (C25/C26B/C27A/C28/C29/C30 ring) having an occupancy of 0.54 (2). With this background, in order to compare with our previous studies the changes in molecular conformation and associated intermolecular interactions due to the presence of different substituents on the invariant group, the crystal structure analysis of the title compound has been carried out.

The thiophene ring is essentially planar with the maximum deviation of 0.005 (3) Å and -0.017 (3) Å for atom C9 and C31 in the two molecules. The six-membered cyclohexene ring adopts a half-chair conformation, with atoms C13 and C14 deviating from the C10/C11/C12/C15 plane by 0.228 (4) and -0.408 (5) Å, for A and the corresponding displacements for atoms C27A and C26B (of the major conformer in molecule B) from the C25/C28/C29/C30 plane are 0.23 (2) and -0.51 (2) Å respectively. The ring-puckering parameters (Cremer & Pople, 1975) generated by PLATON (Spek, 2003) for the cyclohexene ring are Q(2)= 0.324 (3) Å, phi(2) = 200.2 (6)° and theta = 49.8 (4)° in molecule A, with corresponding values of 0.39 (2) Å, 88.0 (12)° and 131.9 (12)° in molecule B (major conformer).

The bond angles C20—C21—C23 and C42—C47—C46 in molecule A and B are 116.9 (2)° and 117.06 (3)° which deviate significantly from the ideal bond angle value of 120°. This deviation is due to the electron-donating inductive effect of the methyl group and similar variations in bond angles has also been observed in 2-[(E)-(4-Chlorophenyl)methylene- amino]-N-(X-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene- 3-carboxamide, where X = 2 and 3 (Vasu et al., 2004a), and in 2-{[(E)-(4-methoxyphenyl)methylene]amino}- N-(3-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3- carboxamide and N-(4-methylphenyl)-2- {[(E)-(4-methylphenyl)methylene]amino}-4,5,6,7-tetrahydro- 1-benzothiophene-3-carboxamide respectively (Vasu et al.,2004(b)). Similarly the bond angles, C8—N1—C7 [121.9 (2)°] and C16—N2—C23 [123.9 (2)°] in molecule A around the azomethane N and amide N atoms are different, indicating the delocalization of the N-atom lone pair of electrons. The corresponding bond angles C41—N4—C42 and C31—N3—C32 in molecule B are 124.2 (2)° and 122.3 (2)° respectively. This is further demonstrated by the bond lengths in the carboxamide and imine moieties being significantly different. In molecule A, the C16—N2 and C8—N1 bond lengths are 1.342 (3) Å and 1.384 (3) Å. The corresponding values (C41···N4 and C31—N3) in molecule B are 1.343 (3) Å and 1.388 (3) Å respectively indicating that the electronic and steric environment around these are different (Table 1). Similarity in bond lengths have been observed in the literature in analogous systems (Vasu et al., 2003, 2004(a) and (b), Kumar et al., 2005).

The angles between the mean planes of the o-toluidine and thiophene rings are 58.6 (1)° and 64.4 (1)° in molecule A and B respectively, indicating sufficient deviation from coplanarity to minimize the steric repulsions between the methoxy group and the hydrogen atoms of the benzene ring (H17 and H18 in molecule A, H43 and H44 in molecule B)·This is further demonstrated by the torsion C17—C23—N2—C16 about the C23—N2 bond in A, and the C43—C42—N4—C41 about the C42—N4 bond in B being -107.6 (3)° and -102.7 (3)° respectively. The benzylideneamino group is essentially planar with the thiophene ring in both molecule A and B. The corresponding dihedral angles being 176.3 (1) Å and 172.1 (1) Å respectively. It is noteworthy, that in case of 2-{[(E)-(4-methoxyphenyl)methylene]amino}- N-(3-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3- carboxamide and N-(4-methylphenyl)-2- {[(E)-(4-methylphenyl)methylene]amino}-4,5,6,7-tetrahydro- 1-benzothiophene-3-carboxamide (Vasu et al., 2004b), the m-toluidine and p-toluidine rings are coplanar with the thiophene rings because of the stabilization imparted, due to electron delocalization and also the absence of steric interactions. The introduction of one methyl group on the N-phenyl ring in the ortho and meta positions, as in case of 2-[(E)-(4-Chlorophenyl)methyleneamino]-N-(2-methylphenyl) -4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide ((Vasu et al., 2004(a)), introduces loss of planarity due to steric interaction between the methyl group and the benzene H atoms bounded to the imine group. The dihedral angles between the mean planes of the m-toluidine and thiophene rings is 18.4 (1)° whereas that between the o-toluidine and thiophene rings is 12.9 (1)°. On addition of a F atom, as in case of 2-[(E)-Benzylideneamino]-N-(2-fluorophenyl)- 4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide (Vasu et al., 2005), the torsion angle is 151.8 (2)° between the o-fluorophenyl and thiophene rings indicating the importance role of sterics in dictating molecular conformation. This deviation from planarity is further increased when a substituent, a methoxy group, in the present compound, was introduced in the phenyl ring attached to imine group as reflected in the values of the dihedral angles observed in the present study.

The conformation of both the molecules in the asymmetric unit is stabilized by intramolecular N—H···N hydrogen bonds which lock the molecular conformation. The crystal structure in the title compound is stabilized by intermolecular O—H···O hydrogen bonds involving the phenolic hydrogen with the carbonyl ring forming C(12) chains (Bernstein et al., 1995) along the crystallographic c axis related by glide plane (Fig. 2, Table 2). >From the packing characteristics, it is interesting to note that the ordered molecule (A) forms molecular chains involving O—H···O hydrogen bonds (involving H1O and O6) with disordered molecules on either side. Similarly, in the parallel chain along [001] direction, the disordered molecule B forms chain with ordered molecules utilizing O—H···O hydrogen bonds (involving H4O and O3). In between parallel layers of molecules the crystal structure is held by van-der Waals forces (Vaas et al., 2003).

In conclusion, the role of different substitutions on the conformational preferences in a series of carboxamide derivatives is highlighted. The associated packing features is mainly through strong hydrogen bonds with cooperativity from van der Waals interactions.

Related literature

For related literature, see: Bernstein et al. (1995); Cohen et al. (1977); Cremer & Pople (1975); Csaszar & Morvay (1983); Dzhurayev et al. (1992); El-Maghraby, Haroun & Mohammed (1984); Gewald et al. (1966); Lakshmi et al. (1985); Pellis & West (1968); Spek (2003); Vasu, Nirmala, Chopra, Mohan & Saravanan (2005); Vasu, Nirmala, Choudhury, Mohan, Saravanan & Narasimhamurthy (2003).

S2. Experimental

The title compound was synthesized using Gewald reaction (Gewald et al., 1966). Ortho-cyanotoluidine (0.04 mol) was refluxed with ethyl methyl ketone in the presence of sulfur at 313–323 K for one hr. The product was then reacted with 4-hydroxy-5-methoxybenzaldehyde in an equi-molar ratio in the presence of ethanol which yielded the title compound (68%). This was purified by recrystallization from ethylacetate by slow evaporation, yielding orange needle-shaped crystals.

S3. Refinement

The hydrogen atoms of the phenolic oxygen, amide nitrogen and the carbon connected to imine nitrogen were located from difference Fourier map and refined isotropically. The N—H and O—H bond lengths are in the range of 0.81 (2)–0.82 (2) Å and 0.86 (4)–0.84 (4) Å respectively. The disordered C26 and C27 atoms of the cyclohexene ring in molecule B were split up and refined using the PART command in SHELXL97.The remaining hydrogen atoms were placed in calculated positions and allowed to ride on the carbon atoms with C—H = 0.93–0.97 Å and U_iso(H) = 1.2 or 1.5U_eq(C).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999) & CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

	Fig. 1. ORTEP view of the two molecules of (I) drawn with 50% ellipsoidal probability·The dotted lines depict intramolecular N—H···N hydrogen bonds.
	Fig. 2. Packing view of the molecules showing O—H···O hydrogen bonds along [001] direction. The molecules at * and # have the symmetry codes at (x - 1/2, - y + 1/2, z - 1/2) and (x + 1/2, - y + 1/2, z - 1/2.)

2-{[(E)-(4-hydroxy-3-methoxyphenyl)methylene]amino}- N-(2-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3- carboxamide

Crystal data

C24H24N2O3S	F(000) = 1776
Mr = 420.52	Dx = 1.308 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 966 reflections
a = 14.817 (8) Å	θ = 1.4–25.2°
b = 13.701 (8) Å	µ = 0.18 mm^−1
c = 22.224 (13) Å	T = 290 K
β = 108.807 (11)°	Needle, orange
V = 4271 (4) Å^3	0.18 × 0.09 × 0.08 mm
Z = 8

Data collection

Bruker SMART CCD area detector diffractometer	7512 independent reflections
Radiation source: fine-focus sealed tube	4900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ϕ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −15→17
Tmin = 0.937, Tmax = 0.986	k = −16→16
30379 measured reflections	l = −25→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0742P)^2 + 0.2254P] where P = (Fo^2 + 2Fc^2)/3
7512 reflections	(Δ/σ)max = 0.001
587 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.89918 (5)	0.92051 (5)	0.25384 (3)	0.0577 (2)
S2	0.37454 (5)	0.27951 (4)	0.25158 (3)	0.0527 (2)
N1	0.88085 (13)	0.72001 (13)	0.25172 (9)	0.0448 (5)
N2	0.82445 (17)	0.65000 (15)	0.34988 (11)	0.0548 (6)
N3	0.35969 (13)	0.07897 (13)	0.24744 (8)	0.0428 (5)
N4	0.32786 (17)	−0.00023 (14)	0.35192 (10)	0.0529 (6)
O1	0.87388 (14)	0.37120 (13)	0.06075 (9)	0.0638 (5)
O2	0.87414 (14)	0.36031 (12)	0.17809 (8)	0.0612 (5)
O3	0.86785 (16)	0.74034 (13)	0.43853 (8)	0.0780 (6)
O4	0.36778 (15)	−0.26720 (14)	0.05810 (10)	0.0712 (6)
O5	0.37704 (14)	−0.27993 (12)	0.17644 (8)	0.0651 (5)
O6	0.36139 (15)	0.09260 (12)	0.43903 (8)	0.0662 (5)
C1	0.88193 (17)	0.45654 (18)	0.09255 (11)	0.0477 (6)
C2	0.89026 (17)	0.54599 (18)	0.06620 (11)	0.0505 (6)
C3	0.89502 (17)	0.63052 (18)	0.10064 (11)	0.0493 (6)
C4	0.89104 (16)	0.62715 (17)	0.16243 (10)	0.0430 (6)
C5	0.88510 (16)	0.53654 (17)	0.18963 (11)	0.0452 (6)
C6	0.88059 (17)	0.45184 (17)	0.15587 (11)	0.0452 (6)
C7	0.89134 (17)	0.71715 (17)	0.19668 (11)	0.0454 (6)
C8	0.88401 (16)	0.80691 (16)	0.28410 (11)	0.0431 (6)
C9	0.87418 (16)	0.81588 (15)	0.34373 (10)	0.0408 (5)
C10	0.88040 (16)	0.91534 (16)	0.36490 (11)	0.0425 (6)
C11	0.89335 (17)	0.97829 (16)	0.32134 (12)	0.0505 (6)
C12	0.9026 (2)	1.08684 (18)	0.32882 (15)	0.0714 (8)
C13	0.9252 (3)	1.1127 (2)	0.39916 (19)	0.0998 (12)
C14	0.8682 (2)	1.0609 (2)	0.43056 (15)	0.0790 (9)
C15	0.87478 (19)	0.95116 (18)	0.42809 (12)	0.0550 (7)
C16	0.85648 (17)	0.73296 (17)	0.38167 (11)	0.0463 (6)
C17	0.8759 (2)	0.4886 (2)	0.38832 (15)	0.0761 (9)
C18	0.8637 (3)	0.4007 (2)	0.41417 (18)	0.0902 (11)
C19	0.7834 (3)	0.3857 (2)	0.43052 (14)	0.0755 (9)
C20	0.7176 (2)	0.4580 (2)	0.42221 (12)	0.0654 (8)
C21	0.72811 (19)	0.54821 (18)	0.39630 (11)	0.0531 (6)
C22	0.6539 (2)	0.6260 (2)	0.38577 (17)	0.0897 (10)
C23	0.80913 (19)	0.56149 (17)	0.37936 (11)	0.0500 (6)
C24	0.8663 (2)	0.35302 (19)	0.24010 (12)	0.0599 (7)
C25	0.3968 (2)	0.44117 (17)	0.33335 (14)	0.0669 (8)
C26A	0.4341 (7)	0.4628 (10)	0.4030 (9)	0.077 (3)	0.50
C26B	0.3885 (7)	0.4694 (9)	0.3980 (8)	0.066 (3)	0.50
C27A	0.4401 (6)	0.3982 (5)	0.4495 (3)	0.0621 (17)	0.50
C27B	0.3779 (6)	0.4115 (5)	0.4393 (4)	0.0667 (18)	0.50
C28	0.38793 (19)	0.29922 (17)	0.43483 (11)	0.0564 (7)
C29	0.37737 (16)	0.26764 (16)	0.36793 (11)	0.0425 (6)
C30	0.38295 (17)	0.33324 (16)	0.32344 (12)	0.0484 (6)
C31	0.36404 (16)	0.16471 (16)	0.28156 (11)	0.0414 (6)
C32	0.37255 (18)	0.07732 (18)	0.19336 (11)	0.0469 (6)
C33	0.37357 (16)	−0.01171 (17)	0.15861 (10)	0.0451 (6)
C34	0.37406 (18)	−0.00763 (19)	0.09607 (11)	0.0540 (7)
C35	0.37160 (18)	−0.09198 (19)	0.06169 (11)	0.0566 (7)
C36	0.37090 (18)	−0.18205 (19)	0.08895 (11)	0.0510 (6)
C37	0.37418 (17)	−0.18761 (17)	0.15321 (11)	0.0476 (6)
C38	0.37430 (16)	−0.10369 (17)	0.18654 (11)	0.0462 (6)
C39	0.3867 (2)	−0.2897 (2)	0.24195 (12)	0.0680 (8)
C40	0.36408 (15)	0.16948 (15)	0.34372 (10)	0.0394 (5)
C41	0.35211 (17)	0.08521 (16)	0.38252 (11)	0.0422 (6)
C42	0.31711 (19)	−0.08931 (16)	0.38188 (10)	0.0477 (6)
C43	0.3863 (2)	−0.16002 (18)	0.38932 (13)	0.0618 (7)
C44	0.3775 (2)	−0.2485 (2)	0.41544 (15)	0.0762 (9)
C45	0.2999 (3)	−0.2670 (2)	0.43451 (14)	0.0763 (9)
C46	0.2312 (2)	−0.1969 (2)	0.42731 (12)	0.0667 (8)
C47	0.23777 (19)	−0.10587 (18)	0.40070 (11)	0.0534 (7)
C48	0.1616 (2)	−0.0310 (2)	0.39172 (17)	0.0840 (10)
H2N	0.8328 (18)	0.6435 (18)	0.3154 (12)	0.059 (9)*
H4N	0.3361 (17)	−0.0037 (18)	0.3178 (12)	0.053 (8)*
H1O	0.871 (2)	0.387 (2)	0.0219 (16)	0.107 (13)*
H4O	0.367 (3)	−0.251 (3)	0.0205 (18)	0.133 (16)*
H2	0.8927	0.5492	0.0249	0.061*
H3	0.9009	0.6904	0.0825	0.059*
H5	0.8842	0.5335	0.2312	0.054*
H7	0.9007 (15)	0.7760 (17)	0.1762 (10)	0.052 (7)*
H12A	0.8436	1.1180	0.3039	0.086*
H12B	0.9533	1.1100	0.3137	0.086*
H13A	0.9919	1.0988	0.4211	0.120*
H13B	0.9157	1.1822	0.4027	0.120*
H14A	0.8021	1.0798	0.4112	0.095*
H14B	0.8878	1.0810	0.4747	0.095*
H15A	0.8193	0.9226	0.4354	0.066*
H15B	0.9309	0.9294	0.4619	0.066*
H17	0.9300	0.4991	0.3767	0.091*
H18	0.9095	0.3519	0.4205	0.108*
H19	0.7737	0.3260	0.4474	0.091*
H20	0.6639	0.4468	0.4342	0.078*
H22A	0.6790	0.6797	0.4140	0.135*
H22B	0.5988	0.6000	0.3940	0.135*
H22C	0.6362	0.6483	0.3426	0.135*
H24A	0.9238	0.3768	0.2708	0.090*
H24B	0.8567	0.2860	0.2491	0.090*
H24C	0.8132	0.3913	0.2422	0.090*
H25A	0.3489	0.4757	0.2999	0.080*	0.50
H25B	0.4591	0.4596	0.3316	0.080*	0.50
H25C	0.4419	0.4640	0.3132	0.080*	0.50
H25D	0.3366	0.4743	0.3136	0.080*	0.50
H26A	0.4150	0.5342	0.4094	0.080*	0.50
H26B	0.3217	0.4716	0.3948	0.080*	0.50
H26C	0.4317	0.5327	0.4094	0.093*	0.50
H26D	0.5003	0.4426	0.4196	0.093*	0.50
H27A	0.4401	0.4221	0.4906	0.075*	0.50
H27B	0.5057	0.3909	0.4506	0.075*	0.50
H27C	0.3113	0.4297	0.4220	0.080*	0.50
H27D	0.4011	0.4315	0.4835	0.080*	0.50
H28A	0.4237	0.2504	0.4647	0.068*	0.50
H28B	0.3254	0.3050	0.4397	0.068*	0.50
H28C	0.4499	0.2791	0.4630	0.068*	0.50
H28D	0.3396	0.2672	0.4487	0.068*	0.50
H32	0.3830 (17)	0.1390 (18)	0.1747 (11)	0.061 (7)*
H34	0.3761	0.0526	0.0773	0.065*
H35	0.3704	−0.0879	0.0197	0.068*
H38	0.3749	−0.1076	0.2284	0.055*
H39A	0.4432	−0.2562	0.2671	0.102*
H39B	0.3914	−0.3575	0.2532	0.102*
H39C	0.3320	−0.2618	0.2497	0.102*
H43	0.4390	−0.1475	0.3765	0.074*
H44	0.4241	−0.2961	0.4202	0.091*
H45	0.2939	−0.3270	0.4523	0.092*
H46	0.1790	−0.2103	0.4405	0.080*
H48A	0.1851	0.0216	0.4212	0.126*
H48B	0.1072	−0.0600	0.3992	0.126*
H48C	0.1435	−0.0063	0.3491	0.126*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0834 (5)	0.0418 (4)	0.0562 (4)	−0.0060 (3)	0.0339 (4)	0.0072 (3)
S2	0.0693 (5)	0.0413 (3)	0.0521 (4)	−0.0005 (3)	0.0257 (3)	0.0080 (3)
N1	0.0583 (13)	0.0396 (11)	0.0417 (12)	−0.0052 (9)	0.0232 (10)	−0.0015 (9)
N2	0.0852 (17)	0.0441 (12)	0.0436 (13)	−0.0118 (11)	0.0323 (12)	0.0012 (10)
N3	0.0531 (12)	0.0428 (11)	0.0341 (11)	−0.0004 (9)	0.0162 (9)	0.0002 (9)
N4	0.0839 (17)	0.0398 (12)	0.0397 (13)	−0.0094 (10)	0.0265 (12)	−0.0023 (10)
O1	0.0926 (15)	0.0566 (11)	0.0464 (12)	0.0059 (10)	0.0281 (11)	−0.0067 (9)
O2	0.0933 (14)	0.0464 (10)	0.0486 (11)	0.0049 (9)	0.0294 (10)	0.0033 (8)
O3	0.1359 (19)	0.0623 (12)	0.0399 (11)	−0.0178 (12)	0.0340 (11)	−0.0005 (9)
O4	0.1042 (17)	0.0631 (13)	0.0490 (12)	0.0173 (11)	0.0283 (11)	−0.0097 (10)
O5	0.0977 (15)	0.0495 (10)	0.0512 (11)	0.0118 (10)	0.0284 (10)	−0.0010 (9)
O6	0.1116 (16)	0.0537 (11)	0.0364 (10)	−0.0121 (10)	0.0281 (10)	−0.0036 (8)
C1	0.0481 (15)	0.0546 (15)	0.0401 (14)	0.0040 (11)	0.0137 (12)	−0.0050 (12)
C2	0.0562 (17)	0.0611 (16)	0.0364 (13)	−0.0005 (12)	0.0181 (12)	−0.0019 (12)
C3	0.0546 (16)	0.0540 (15)	0.0425 (14)	−0.0054 (12)	0.0199 (12)	0.0040 (12)
C4	0.0441 (15)	0.0496 (14)	0.0358 (13)	−0.0035 (11)	0.0138 (11)	−0.0005 (11)
C5	0.0521 (16)	0.0515 (14)	0.0331 (13)	0.0006 (11)	0.0156 (11)	0.0016 (11)
C6	0.0487 (15)	0.0498 (14)	0.0383 (14)	0.0026 (11)	0.0157 (11)	0.0015 (11)
C7	0.0513 (16)	0.0431 (14)	0.0425 (15)	−0.0067 (11)	0.0160 (12)	0.0053 (11)
C8	0.0506 (15)	0.0394 (13)	0.0414 (14)	−0.0029 (10)	0.0177 (11)	0.0051 (10)
C9	0.0452 (14)	0.0402 (13)	0.0373 (13)	−0.0032 (10)	0.0137 (11)	0.0003 (10)
C10	0.0389 (14)	0.0424 (13)	0.0446 (14)	−0.0026 (10)	0.0111 (11)	−0.0016 (11)
C11	0.0547 (16)	0.0401 (13)	0.0571 (16)	−0.0045 (11)	0.0187 (13)	−0.0015 (12)
C12	0.082 (2)	0.0395 (15)	0.096 (2)	−0.0055 (13)	0.0340 (18)	−0.0006 (15)
C13	0.128 (3)	0.0551 (19)	0.136 (3)	−0.0235 (19)	0.069 (3)	−0.039 (2)
C14	0.096 (2)	0.0623 (19)	0.074 (2)	0.0007 (17)	0.0209 (18)	−0.0195 (16)
C15	0.0559 (17)	0.0568 (16)	0.0501 (15)	−0.0015 (12)	0.0140 (13)	−0.0127 (12)
C16	0.0574 (16)	0.0446 (14)	0.0405 (14)	−0.0019 (11)	0.0206 (12)	0.0019 (11)
C17	0.087 (2)	0.0586 (18)	0.101 (2)	0.0050 (16)	0.0556 (19)	0.0126 (17)
C18	0.109 (3)	0.0508 (19)	0.124 (3)	0.0155 (17)	0.055 (2)	0.0181 (18)
C19	0.110 (3)	0.0449 (16)	0.073 (2)	−0.0146 (17)	0.0305 (19)	0.0109 (14)
C20	0.078 (2)	0.0648 (19)	0.0587 (17)	−0.0227 (16)	0.0300 (15)	0.0060 (14)
C21	0.0619 (18)	0.0540 (15)	0.0454 (15)	−0.0102 (13)	0.0200 (13)	0.0008 (12)
C22	0.080 (2)	0.082 (2)	0.121 (3)	0.0105 (18)	0.052 (2)	0.022 (2)
C23	0.0712 (18)	0.0417 (13)	0.0415 (14)	−0.0085 (12)	0.0243 (13)	0.0016 (11)
C24	0.0745 (19)	0.0559 (16)	0.0497 (16)	−0.0003 (13)	0.0205 (14)	0.0100 (12)
C25	0.078 (2)	0.0388 (14)	0.089 (2)	−0.0020 (13)	0.0340 (17)	−0.0002 (14)
C26A	0.074 (8)	0.048 (5)	0.112 (8)	−0.020 (6)	0.033 (9)	−0.026 (5)
C26B	0.063 (7)	0.045 (4)	0.089 (6)	−0.003 (6)	0.021 (7)	−0.024 (4)
C27A	0.069 (5)	0.051 (4)	0.066 (4)	−0.013 (4)	0.019 (4)	−0.019 (3)
C27B	0.072 (5)	0.055 (4)	0.073 (5)	−0.008 (4)	0.023 (5)	−0.017 (3)
C28	0.0707 (18)	0.0488 (14)	0.0509 (15)	−0.0103 (12)	0.0213 (13)	−0.0126 (12)
C29	0.0412 (14)	0.0389 (13)	0.0474 (14)	−0.0027 (10)	0.0141 (11)	−0.0035 (11)
C30	0.0500 (15)	0.0401 (13)	0.0580 (16)	−0.0013 (11)	0.0215 (13)	−0.0014 (12)
C31	0.0430 (14)	0.0380 (13)	0.0430 (14)	−0.0020 (10)	0.0137 (11)	0.0031 (10)
C32	0.0565 (16)	0.0449 (14)	0.0397 (14)	0.0021 (12)	0.0161 (12)	0.0054 (11)
C33	0.0477 (15)	0.0508 (14)	0.0367 (13)	0.0054 (11)	0.0133 (11)	−0.0011 (11)
C34	0.0675 (18)	0.0583 (16)	0.0411 (14)	0.0079 (13)	0.0242 (13)	0.0063 (12)
C35	0.0660 (18)	0.0708 (19)	0.0336 (14)	0.0141 (14)	0.0170 (12)	−0.0030 (13)
C36	0.0535 (16)	0.0583 (16)	0.0410 (15)	0.0132 (12)	0.0153 (12)	−0.0061 (12)
C37	0.0485 (15)	0.0521 (15)	0.0420 (14)	0.0089 (11)	0.0141 (12)	−0.0016 (12)
C38	0.0492 (15)	0.0568 (15)	0.0336 (13)	0.0078 (11)	0.0147 (11)	0.0004 (11)
C39	0.091 (2)	0.0581 (17)	0.0580 (18)	0.0024 (15)	0.0274 (16)	0.0057 (13)
C40	0.0416 (14)	0.0370 (12)	0.0393 (13)	0.0013 (10)	0.0128 (11)	−0.0019 (10)
C41	0.0501 (15)	0.0404 (13)	0.0367 (14)	−0.0012 (10)	0.0149 (11)	−0.0009 (10)
C42	0.0681 (18)	0.0373 (13)	0.0374 (13)	−0.0077 (12)	0.0166 (12)	−0.0011 (10)
C43	0.069 (2)	0.0498 (16)	0.0680 (18)	−0.0069 (14)	0.0235 (15)	−0.0037 (13)
C44	0.094 (3)	0.0446 (16)	0.081 (2)	0.0081 (16)	0.0167 (19)	0.0065 (15)
C45	0.118 (3)	0.0420 (16)	0.0635 (19)	−0.0134 (18)	0.0225 (19)	0.0081 (14)
C46	0.093 (2)	0.0612 (18)	0.0526 (17)	−0.0228 (16)	0.0321 (16)	−0.0012 (14)
C47	0.0640 (18)	0.0525 (15)	0.0448 (15)	−0.0084 (13)	0.0190 (13)	−0.0025 (12)
C48	0.078 (2)	0.078 (2)	0.107 (3)	0.0032 (17)	0.043 (2)	0.0049 (19)

Geometric parameters (Å, º)

C27A—C26B	1.511 (17)	C39—H39B	0.9600
C27A—C28	1.543 (7)	C39—H39C	0.9600
C27A—H27A	0.9700	C45—C44	1.370 (4)
C27A—H27B	0.9700	C45—H45	0.9300
C26B—C25	1.530 (15)	C44—H44	0.9300
C26B—H26A	0.9700	S1—C11	1.722 (3)
C26B—H26B	0.9700	S1—C8	1.738 (2)
C27B—C26A	1.508 (17)	O1—C1	1.352 (3)
C27B—C28	1.552 (8)	O1—H1O	0.89 (3)
C27B—H27C	0.9700	O2—C6	1.362 (3)
C27B—H27D	0.9700	O2—C24	1.422 (3)
C26A—C25	1.496 (17)	O3—C16	1.223 (3)
C26A—H26C	0.9700	C5—C6	1.371 (3)
C26A—H26D	0.9700	C5—C4	1.396 (3)
C25—C30	1.499 (3)	C5—H5	0.9300
C25—H25A	0.9700	N1—C7	1.283 (3)
C25—H25B	0.9700	N1—C8	1.384 (3)
C25—H25C	0.9700	C9—C8	1.384 (3)
C25—H25D	0.9700	C9—C10	1.435 (3)
C28—C29	1.508 (3)	C9—C16	1.489 (3)
C28—H28A	0.9700	N2—C16	1.342 (3)
C28—H28B	0.9700	N2—C23	1.431 (3)
C28—H28C	0.9700	N2—H2N	0.82 (2)
C28—H28D	0.9700	C1—C2	1.380 (3)
S2—C30	1.726 (3)	C1—C6	1.415 (3)
S2—C31	1.735 (2)	C4—C3	1.395 (3)
N3—C32	1.277 (3)	C4—C7	1.448 (3)
N3—C31	1.388 (3)	C10—C11	1.355 (3)
O6—C41	1.222 (3)	C10—C15	1.516 (3)
O4—C36	1.346 (3)	C23—C17	1.374 (4)
O4—H4O	0.86 (4)	C23—C21	1.381 (3)
O5—C37	1.362 (3)	C7—H7	0.97 (2)
O5—C39	1.422 (3)	C3—C2	1.378 (3)
N4—C41	1.344 (3)	C3—H3	0.9300
N4—C42	1.424 (3)	C2—H2	0.9300
N4—H4N	0.81 (2)	C20—C19	1.360 (4)
C40—C31	1.382 (3)	C20—C21	1.395 (3)
C40—C29	1.438 (3)	C20—H20	0.9300
C40—C41	1.486 (3)	C11—C12	1.497 (3)
C32—C33	1.446 (3)	C21—C22	1.493 (4)
C32—H32	0.97 (2)	C24—H24A	0.9600
C36—C35	1.377 (3)	C24—H24B	0.9600
C36—C37	1.416 (3)	C24—H24C	0.9600
C29—C30	1.360 (3)	C15—C14	1.510 (4)
C38—C37	1.366 (3)	C15—H15A	0.9700
C38—C33	1.403 (3)	C15—H15B	0.9700
C38—H38	0.9300	C19—C18	1.364 (4)
C42—C43	1.379 (3)	C19—H19	0.9300
C42—C47	1.387 (3)	C12—C13	1.533 (4)
C35—C34	1.379 (3)	C12—H12A	0.9700
C35—H35	0.9300	C12—H12B	0.9700
C47—C46	1.397 (3)	C22—H22A	0.9600
C47—C48	1.490 (4)	C22—H22B	0.9600
C33—C34	1.393 (3)	C22—H22C	0.9600
C34—H34	0.9300	C17—C18	1.372 (4)
C46—C45	1.368 (4)	C17—H17	0.9300
C46—H46	0.9300	C13—C14	1.442 (4)
C43—C44	1.369 (4)	C13—H13A	0.9700
C43—H43	0.9300	C13—H13B	0.9700
C48—H48A	0.9600	C14—H14A	0.9700
C48—H48B	0.9600	C14—H14B	0.9700
C48—H48C	0.9600	C18—H18	0.9300
C39—H39A	0.9600
C26B—C27A—C28	108.1 (7)	C47—C48—H48A	109.5
C26B—C27A—H27A	110.1	C47—C48—H48B	109.5
C28—C27A—H27A	110.1	H48A—C48—H48B	109.5
C26B—C27A—H27B	110.1	C47—C48—H48C	109.5
C28—C27A—H27B	110.1	H48A—C48—H48C	109.5
H27A—C27A—H27B	108.4	H48B—C48—H48C	109.5
C27A—C26B—C25	112.0 (7)	O5—C39—H39A	109.5
C27A—C26B—H26A	109.2	O5—C39—H39B	109.5
C25—C26B—H26A	109.2	H39A—C39—H39B	109.5
C27A—C26B—H26B	109.2	O5—C39—H39C	109.5
C25—C26B—H26B	109.2	H39A—C39—H39C	109.5
H26A—C26B—H26B	107.9	H39B—C39—H39C	109.5
C26A—C27B—C28	110.3 (7)	C46—C45—C44	119.9 (3)
C26A—C27B—H27C	109.6	C46—C45—H45	120.0
C28—C27B—H27C	109.6	C44—C45—H45	120.0
C26A—C27B—H27D	109.6	C43—C44—C45	119.9 (3)
C28—C27B—H27D	109.6	C43—C44—H44	120.0
H27C—C27B—H27D	108.1	C45—C44—H44	120.0
C25—C26A—C27B	112.2 (8)	C11—S1—C8	91.46 (11)
C25—C26A—H26C	109.2	C1—O1—H1O	105 (2)
C27B—C26A—H26C	109.2	C6—O2—C24	116.93 (18)
C25—C26A—H26D	109.2	C6—C5—C4	121.0 (2)
C27B—C26A—H26D	109.2	C6—C5—H5	119.5
H26C—C26A—H26D	107.9	C4—C5—H5	119.5
C26A—C25—C30	109.6 (6)	C7—N1—C8	121.89 (19)
C30—C25—C26B	109.9 (6)	C8—C9—C10	112.52 (19)
C26A—C25—H25A	129.2	C8—C9—C16	124.58 (19)
C30—C25—H25A	109.7	C10—C9—C16	122.9 (2)
C26B—C25—H25A	109.7	C16—N2—C23	123.9 (2)
C26A—C25—H25B	87.2	C16—N2—H2N	117.2 (18)
C30—C25—H25B	109.7	C23—N2—H2N	115.2 (17)
C26B—C25—H25B	109.7	O1—C1—C2	123.4 (2)
H25A—C25—H25B	108.2	O1—C1—C6	117.0 (2)
C26A—C25—H25C	109.5	C2—C1—C6	119.6 (2)
C30—C25—H25C	109.4	O2—C6—C5	125.3 (2)
C26B—C25—H25C	128.9	O2—C6—C1	115.3 (2)
H25A—C25—H25C	86.0	C5—C6—C1	119.4 (2)
C26A—C25—H25D	110.9	C3—C4—C5	118.9 (2)
C30—C25—H25D	109.4	C3—C4—C7	119.7 (2)
C26B—C25—H25D	88.1	C5—C4—C7	121.3 (2)
H25B—C25—H25D	127.4	C9—C8—N1	125.27 (19)
H25C—C25—H25D	108.0	C9—C8—S1	110.93 (16)
C29—C28—C27A	110.3 (3)	N1—C8—S1	123.79 (16)
C29—C28—C27B	111.5 (4)	C11—C10—C9	112.2 (2)
C29—C28—H28A	109.6	C11—C10—C15	121.3 (2)
C27A—C28—H28A	109.6	C9—C10—C15	126.5 (2)
C27B—C28—H28A	133.0	C17—C23—C21	120.9 (2)
C29—C28—H28B	109.6	C17—C23—N2	118.0 (2)
C27A—C28—H28B	109.6	C21—C23—N2	121.1 (2)
C27B—C28—H28B	78.3	N1—C7—C4	123.2 (2)
H28A—C28—H28B	108.1	N1—C7—H7	120.4 (13)
C29—C28—H28C	109.3	C4—C7—H7	116.5 (13)
C27A—C28—H28C	78.9	C2—C3—C4	120.6 (2)
C27B—C28—H28C	109.3	C2—C3—H3	119.7
H28B—C28—H28C	133.7	C4—C3—H3	119.7
C29—C28—H28D	109.3	O3—C16—N2	121.4 (2)
C27A—C28—H28D	134.5	O3—C16—C9	122.1 (2)
C27B—C28—H28D	109.4	N2—C16—C9	116.4 (2)
H28A—C28—H28D	76.6	C3—C2—C1	120.4 (2)
H28C—C28—H28D	108.0	C3—C2—H2	119.8
C30—S2—C31	91.17 (11)	C1—C2—H2	119.8
C32—N3—C31	122.33 (19)	C19—C20—C21	122.2 (3)
C36—O4—H4O	106 (2)	C19—C20—H20	118.9
C37—O5—C39	117.11 (19)	C21—C20—H20	118.9
C41—N4—C42	124.2 (2)	C10—C11—C12	125.5 (2)
C41—N4—H4N	115.5 (17)	C10—C11—S1	112.83 (17)
C42—N4—H4N	117.5 (17)	C12—C11—S1	121.62 (19)
C31—C40—C29	111.99 (19)	C23—C21—C20	116.7 (2)
C31—C40—C41	125.58 (19)	C23—C21—C22	121.7 (2)
C29—C40—C41	122.4 (2)	C20—C21—C22	121.6 (3)
C40—C31—N3	124.82 (19)	O2—C24—H24A	109.5
C40—C31—S2	111.69 (16)	O2—C24—H24B	109.5
N3—C31—S2	123.45 (17)	H24A—C24—H24B	109.5
O6—C41—N4	121.0 (2)	O2—C24—H24C	109.5
O6—C41—C40	122.5 (2)	H24A—C24—H24C	109.5
N4—C41—C40	116.5 (2)	H24B—C24—H24C	109.5
N3—C32—C33	123.3 (2)	C14—C15—C10	112.3 (2)
N3—C32—H32	118.4 (14)	C14—C15—H15A	109.1
C33—C32—H32	118.4 (14)	C10—C15—H15A	109.1
O4—C36—C35	123.8 (2)	C14—C15—H15B	109.1
O4—C36—C37	116.9 (2)	C10—C15—H15B	109.1
C35—C36—C37	119.3 (2)	H15A—C15—H15B	107.9
C30—C29—C40	112.3 (2)	C20—C19—C18	120.1 (3)
C30—C29—C28	121.1 (2)	C20—C19—H19	119.9
C40—C29—C28	126.6 (2)	C18—C19—H19	119.9
C37—C38—C33	121.1 (2)	C11—C12—C13	108.9 (2)
C37—C38—H38	119.4	C11—C12—H12A	109.9
C33—C38—H38	119.4	C13—C12—H12A	109.9
C43—C42—C47	121.2 (2)	C11—C12—H12B	109.9
C43—C42—N4	117.9 (2)	C13—C12—H12B	109.9
C47—C42—N4	120.9 (2)	H12A—C12—H12B	108.3
O5—C37—C38	125.6 (2)	C21—C22—H22A	109.5
O5—C37—C36	114.8 (2)	C21—C22—H22B	109.5
C38—C37—C36	119.7 (2)	H22A—C22—H22B	109.5
C36—C35—C34	120.7 (2)	C21—C22—H22C	109.5
C36—C35—H35	119.7	H22A—C22—H22C	109.5
C34—C35—H35	119.7	H22B—C22—H22C	109.5
C29—C30—C25	125.6 (2)	C18—C17—C23	120.9 (3)
C29—C30—S2	112.79 (17)	C18—C17—H17	119.6
C25—C30—S2	121.56 (19)	C23—C17—H17	119.6
C42—C47—C46	117.0 (2)	C14—C13—C12	114.2 (3)
C42—C47—C48	121.8 (2)	C14—C13—H13A	108.7
C46—C47—C48	121.3 (3)	C12—C13—H13A	108.7
C34—C33—C38	118.4 (2)	C14—C13—H13B	108.7
C34—C33—C32	120.2 (2)	C12—C13—H13B	108.7
C38—C33—C32	121.4 (2)	H13A—C13—H13B	107.6
C35—C34—C33	120.8 (2)	C13—C14—C15	114.6 (3)
C35—C34—H34	119.6	C13—C14—H14A	108.6
C33—C34—H34	119.6	C15—C14—H14A	108.6
C45—C46—C47	121.7 (3)	C13—C14—H14B	108.6
C45—C46—H46	119.1	C15—C14—H14B	108.6
C47—C46—H46	119.1	H14A—C14—H14B	107.6
C44—C43—C42	120.2 (3)	C19—C18—C17	119.2 (3)
C44—C43—H43	119.9	C19—C18—H18	120.4
C42—C43—H43	119.9	C17—C18—H18	120.4
C28—C27A—C26B—C25	−66.5 (10)	C47—C42—C43—C44	0.2 (4)
C28—C27B—C26A—C25	63.8 (11)	N4—C42—C43—C44	−177.3 (2)
C27B—C26A—C25—C30	−48.3 (10)	C47—C46—C45—C44	0.3 (4)
C27B—C26A—C25—C26B	46.8 (18)	C42—C43—C44—C45	−0.3 (4)
C27A—C26B—C25—C26A	−51.2 (19)	C46—C45—C44—C43	0.0 (4)
C27A—C26B—C25—C30	42.7 (9)	C24—O2—C6—C5	3.5 (3)
C26B—C27A—C28—C29	53.1 (8)	C24—O2—C6—C1	−176.0 (2)
C26B—C27A—C28—C27B	−45.6 (8)	C4—C5—C6—O2	−179.6 (2)
C26A—C27B—C28—C29	−44.5 (9)	C4—C5—C6—C1	−0.1 (3)
C26A—C27B—C28—C27A	50.1 (8)	O1—C1—C6—O2	1.8 (3)
C29—C40—C31—N3	174.9 (2)	C2—C1—C6—O2	−178.7 (2)
C41—C40—C31—N3	−5.0 (4)	O1—C1—C6—C5	−177.7 (2)
C29—C40—C31—S2	−2.9 (2)	C2—C1—C6—C5	1.8 (3)
C41—C40—C31—S2	177.24 (17)	C6—C5—C4—C3	−1.8 (3)
C32—N3—C31—C40	−170.5 (2)	C6—C5—C4—C7	177.1 (2)
C32—N3—C31—S2	7.0 (3)	C10—C9—C8—N1	−179.8 (2)
C30—S2—C31—C40	1.88 (18)	C16—C9—C8—N1	−1.3 (4)
C30—S2—C31—N3	−175.9 (2)	C10—C9—C8—S1	−0.9 (3)
C42—N4—C41—O6	−4.3 (4)	C16—C9—C8—S1	177.62 (18)
C42—N4—C41—C40	177.3 (2)	C7—N1—C8—C9	−179.5 (2)
C31—C40—C41—O6	173.1 (2)	C7—N1—C8—S1	1.8 (3)
C29—C40—C41—O6	−6.8 (4)	C11—S1—C8—C9	0.59 (19)
C31—C40—C41—N4	−8.5 (3)	C11—S1—C8—N1	179.5 (2)
C29—C40—C41—N4	171.6 (2)	C8—C9—C10—C11	0.8 (3)
C31—N3—C32—C33	176.5 (2)	C16—C9—C10—C11	−177.7 (2)
C31—C40—C29—C30	2.6 (3)	C8—C9—C10—C15	−178.5 (2)
C41—C40—C29—C30	−177.5 (2)	C16—C9—C10—C15	2.9 (4)
C31—C40—C29—C28	−175.6 (2)	C16—N2—C23—C17	−102.8 (3)
C41—C40—C29—C28	4.3 (4)	C16—N2—C23—C21	79.5 (3)
C27A—C28—C29—C30	−20.9 (4)	C8—N1—C7—C4	178.2 (2)
C27B—C28—C29—C30	15.0 (4)	C3—C4—C7—N1	174.8 (2)
C27A—C28—C29—C40	157.1 (4)	C5—C4—C7—N1	−4.1 (4)
C27B—C28—C29—C40	−166.9 (4)	C5—C4—C3—C2	2.0 (3)
C41—N4—C42—C43	−107.6 (3)	C7—C4—C3—C2	−176.9 (2)
C41—N4—C42—C47	74.9 (3)	C23—N2—C16—O3	−5.8 (4)
C39—O5—C37—C38	−3.9 (4)	C23—N2—C16—C9	176.2 (2)
C39—O5—C37—C36	176.0 (2)	C8—C9—C16—O3	164.4 (2)
C33—C38—C37—O5	178.3 (2)	C10—C9—C16—O3	−17.2 (4)
C33—C38—C37—C36	−1.6 (4)	C8—C9—C16—N2	−17.6 (3)
O4—C36—C37—O5	2.3 (3)	C10—C9—C16—N2	160.8 (2)
C35—C36—C37—O5	−177.5 (2)	C4—C3—C2—C1	−0.3 (4)
O4—C36—C37—C38	−177.8 (2)	O1—C1—C2—C3	177.9 (2)
C35—C36—C37—C38	2.4 (4)	C6—C1—C2—C3	−1.6 (4)
O4—C36—C35—C34	179.4 (2)	C9—C10—C11—C12	180.0 (2)
C37—C36—C35—C34	−0.8 (4)	C15—C10—C11—C12	−0.6 (4)
C40—C29—C30—C25	180.0 (2)	C9—C10—C11—S1	−0.3 (3)
C28—C29—C30—C25	−1.7 (4)	C15—C10—C11—S1	179.04 (18)
C40—C29—C30—S2	−1.2 (3)	C8—S1—C11—C10	−0.13 (19)
C28—C29—C30—S2	177.15 (18)	C8—S1—C11—C12	179.5 (2)
C26A—C25—C30—C29	17.9 (5)	C17—C23—C21—C20	−0.3 (4)
C26B—C25—C30—C29	−8.7 (5)	N2—C23—C21—C20	177.3 (2)
C26A—C25—C30—S2	−160.9 (4)	C17—C23—C21—C22	−178.9 (3)
C26B—C25—C30—S2	172.6 (4)	N2—C23—C21—C22	−1.3 (4)
C31—S2—C30—C29	−0.38 (19)	C19—C20—C21—C23	−0.2 (4)
C31—S2—C30—C25	178.5 (2)	C19—C20—C21—C22	178.4 (3)
C43—C42—C47—C46	0.0 (3)	C11—C10—C15—C14	9.9 (3)
N4—C42—C47—C46	177.5 (2)	C9—C10—C15—C14	−170.9 (2)
C43—C42—C47—C48	−178.7 (3)	C21—C20—C19—C18	0.9 (5)
N4—C42—C47—C48	−1.3 (4)	C10—C11—C12—C13	16.9 (4)
C37—C38—C33—C34	−0.8 (3)	S1—C11—C12—C13	−162.8 (2)
C37—C38—C33—C32	179.3 (2)	C21—C23—C17—C18	0.1 (5)
N3—C32—C33—C34	170.7 (2)	N2—C23—C17—C18	−177.6 (3)
N3—C32—C33—C38	−9.5 (4)	C11—C12—C13—C14	−44.6 (4)
C36—C35—C34—C33	−1.6 (4)	C12—C13—C14—C15	57.7 (4)
C38—C33—C34—C35	2.5 (4)	C10—C15—C14—C13	−38.0 (4)
C32—C33—C34—C35	−177.7 (2)	C20—C19—C18—C17	−1.2 (5)
C42—C47—C46—C45	−0.3 (4)	C23—C17—C18—C19	0.7 (5)
C48—C47—C46—C45	178.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···N3	0.81 (3)	2.05 (3)	2.738 (3)	143 (2)
N2—H2N···N1	0.82 (3)	2.06 (3)	2.748 (4)	141 (2)
O4—H4O···O3^i	0.86 (4)	1.83 (4)	2.683 (3)	171 (4)
O1—H1O···O6^ii	0.88 (4)	1.82 (4)	2.697 (3)	174 (3)
C35—H35···Cg1^iii	0.93	2.89	3.670 (3)	143

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1, −y, −z.