Three 2-amino­purine derivatives

The structure of 2-amino-6-chloro­purine, C₅H₄ClN₅, (I), comprises a flat mol­ecule, with all possible strong hydrogen-bond donors and acceptors involved in the hydrogen-bonding network. The structures of 2-amino-6-(4-chloro­phenylsulfanyl)­purine hemihydrate, C₁₁H₈ClN₅S·0.5H₂O, (II), and 2-amino-6-(4-methylphenylsulfanyl)purine 0.33-hydrate, C₁₂H₁₁N₅S·0.33H₂O, (III), have two and three unique mol­ecules, respectively, and one water mol­ecule in their asymmetric units. Both (II) and (III) exhibit elaborate hydrogen-bonding networks that involve the S (for both) and Cl [for (II)] atoms in addition to the expected strong hydrogen-bonding sites. Both structures also have offset-stacking formations of the phenyl and purine rings.

S1. Comment

Purine bases play an important role in the chemistry of life. Two purine bases, adenine and guanine, are found as major components of DNA and RNA. In these systems, attachment to the deoxyribose or ribose groups occurs via N9. Similarly, of the 549 reported structures (Cambridge Structural Database, April 2002 release; Allen, 2002) containing a purine group, the vast majority also contain N9 substituents other than an H atom, with only 92 purine structures exhibiting an N9—H group. There are 34 2-aminopurine structures, of which only two have N9—H; these are N-(2-amino-6-purinyl)pyridinium chloride dihydrate (Jaskolski et al., 1987) and potassium 2-amino-6-sulfinatopurine monohydrate (Horn & Tiekink, 1995). The hydrogen-bonding patterns in both are dominated by the counter-ions. We report here the crystal structures of three 2-aminopurine derivatives containing N9—H, namely 2-amino-6-chloropurine, (I), 2-amino-6-(4-chlorophenylthio)purine hemihydrate, (II), and 2-amino-6-(4-methylphenylthio)purine 0.33-hydrate, (III). Compounds (II) and (III) were both derived by the nucleophilic addition of a thiophenol derivative to (I).

Compound (I) is a flat molecule [r.m.s. deviation 0.010 (2) Å] with three strong hydrogen-bond donor atoms and three strong hydrogen-bond acceptor atoms (neglecting the N atom in NH₂), plus the Cl atom that can be considered as a weak acceptor (Fig. 1). This equality in numbers of strong hydrogen-bonding agents is reflected in the hydrogen-bonding network with all possible strong hydrogen-bonding sites occupied (Table 1). N9—H associates with N7 and creates a flat hydrogen-bond chain with molecules of alternating directions inclined to the (001) plane (Fig. 2). The associations between atoms N2, N31 and N4 form a convoluted hydrogen-bonded ribbon network similar to 2-aminopyrimidine and subsequent derivatives (Lynch et al., 2002). Thus, each molecule associates with two molecules via pairwise interactions and with two others through single interactions. The Cl atom resides in a position that is approximated by H8(1 + y, x, −z) [3.121 (3) Å], but the distance is too far to be listed as a formal C—H···Cl close contact.

The asymmetric unit of (II) consists of two unique 2-amino-6-(4-chlorophenylthio)purine molecules with one water molecule (Fig. 3). This combination gives eight strong hydrogen-bond donors and seven strong acceptors per asymmetric unit (neglecting the N atoms of the NH₂ groups), plus two S atoms and two Cl atoms, both considered to act as weak hydrogen-bonding acceptors. All of these sites are involved in the hydrogen-bonding array, except for two acceptors, N1B and Cl6A (Table 2), although the Cl atom is approached by H8B(−1 + x,1 + y, z) [2.733 (3) Å]. Molecules A and B and the water molecule form a hydrogen-bonded ring [graph-set notation R³₃(10); Bernstein et al., 1995] through N9A—H···N3B, N9B—H···O1W and O1W—H···N3A hydrogen bonds. The 2-amino group of molecule A associates with N7A through one H atom and with both N1A and S6A through the H atom. The 2-amino group of molecule B is involved in a similar arrangement, with one H associating with N7B and the other associating with both Cl6B and S6B. The remaining water H atom also associates with S6B. The resulting network is very complex and difficult to represent in a single-view packing diagram (Fig. 4). The phenyl rings are significantly inclined to the purine rings with respective dihedral angles for molecules A and B of 72.21 (6) and 79.57 (8)°. Such angles allow the phenyl rings of molecule A to form alternating slipped-stacks with the purine rings of like molecules [interlayer distances ca 3.40 (4) Å and angle 2.26 (2)°]. For molecule B, the slipped-stacks are only formed by symmetry-related phenyl rings of alternating directions [interlayer distance 3.483 (3) Å], which are coplanar by symmetry.

The asymmetric unit of (III) consists of three unique 2-amino-6-(4-methylphenylthio)purine molecules and one water molecule (Fig. 5). This combination gives eight strong hydrogen-bond donors, seven strong acceptors (neglecting the N atoms of the NH₂ groups) and three S atoms. Molecules A and B associate via a single hydrogen bond (N9A—H···N7B) and also via a N21A—H···N3A dimer to form a linked tetramer that is `capped' at both ends by an association from N9B—H to the water molecule. This water molecule, O1W, through one H atom, then associates to N7C. Molecule C, through N9C—H and N3C, forms a dimer with N3B and N21B—H. The full list of hydrogen bonds in (III) is given in Table 3 although additional noteworthy interactions are the two three-centre associations, one from N21C to N1A and N21A (note the use in this structure of a NH₂ group as an hydrogen-bond acceptor) and the other from the water molecule to atoms N7A and S6A. There are no close contacts with one H atom of N21C. Again, the hydrogen-bonding network is very extensive and difficult to represent in a single-view packing diagram (Fig. 6). The dihedral angles between the phenyl ring and the purine for molecules A, B and C are 73.08 (7), 63.21 (8) and 80.80 (8)°, respectively, and again allow for slipped-stacks. A triplet of phenyl-A, purine-C and purine-B has the respective interlayer distances and angles of 3.2 (2) Å and 12.34 (4)°, and 3.4 (1) Å and 15.92 (4)°, whereas a tetramer of purine-A, phenyl-C, phenyl-C and purine-A has similar values of 3.62 (4) Å and 15.46 (4)°, and 3.679 (3) Å and 0.02 (4)°. The only ring system not to partake in stacking arrangements is phenyl-B.

S2. Experimental

All compounds were obtained from Key Organics Ltd and crystals were grown from ethanol solution.

S3. Refinement

All H atoms were included in the refinement, at calculated positions, as riding models, with C—H set to 0.95 (Ar—H) and 0.98 Å (CH₃), and N—H set to 0.88 Å, except for the water H atoms, which were located in difference syntheses and for which both positional and displacement parameters were refined. For (I), the number of Friedel pairs is 548. A high R_int value of 0.111 for (III) results from the weak high-angle data.

Computing details

For all compounds, data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular configuration and atom-numbering scheme for (I), showing ellipsoids at the 50% probability level.
	Fig. 2. Packing diagram for (I), viewed down the a axis, showing both single and pair-wise hydrogen-bonding associations (dotted lines) to and from each molecule.
	Fig. 3. The molecular configuration and atom-numbering scheme for (II), showing ellipsoids at the 50% probability level.
	Fig. 4. Packing diagram for (II), viewed down the b axis, showing the stacking arrangements and a portion of the complex hydrogen-bonding network.
	Fig. 5. The molecular configuration and atom-numbering scheme for (III), showing ellipsoids at the 50% probability level.
	Fig. 6. Packing diagram of (III), showing the stacking arrangements and the major hydrogen-bonding associations.

(I) 2-amino-6-chloropurine

Crystal data

C5H4ClN5	Dx = 1.663 Mg m^−3
Mr = 169.58	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 8615 reflections
a = 7.0855 (10) Å	θ = 2.9–27.5°
c = 26.990 (5) Å	µ = 0.49 mm^−1
V = 1355.0 (4) Å^3	T = 150 K
Z = 8	Rectangular prism, colourless
F(000) = 688	0.15 × 0.08 × 0.07 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer	1535 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1151 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −5→9
Tmin = 0.910, Tmax = 0.964	l = −24→34
4943 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0335P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1535 reflections	Δρmax = 0.26 e Å^−3
100 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Absolute structure: Flack (1983), 548 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (10)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4911 (3)	0.6115 (3)	0.09891 (7)	0.0187 (5)
C2	0.3717 (3)	0.4593 (4)	0.09459 (8)	0.0181 (6)
N21	0.2115 (3)	0.4681 (3)	0.12083 (7)	0.0261 (6)
H21	0.1297	0.3748	0.1194	0.033*
H22	0.1881	0.5672	0.1395	0.033*
N3	0.4012 (3)	0.3036 (3)	0.06637 (7)	0.0180 (5)
C4	0.5651 (3)	0.3104 (4)	0.04214 (8)	0.0159 (6)
C5	0.6988 (4)	0.4549 (3)	0.04394 (8)	0.0155 (6)
C6	0.6494 (3)	0.6054 (4)	0.07369 (8)	0.0157 (6)
Cl6	0.79634 (9)	0.79992 (9)	0.07836 (2)	0.02353 (18)
N7	0.8518 (3)	0.4129 (3)	0.01381 (7)	0.0195 (5)
C8	0.8073 (3)	0.2481 (3)	−0.00486 (9)	0.0216 (6)
H8	0.8869	0.1817	−0.0272	0.027*
N9	0.6365 (3)	0.1797 (3)	0.01049 (6)	0.0182 (5)
H9	0.5835	0.0725	0.0016	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0191 (12)	0.0158 (12)	0.0211 (11)	0.0017 (10)	−0.0005 (9)	0.0008 (10)
C2	0.0174 (14)	0.0160 (14)	0.0209 (13)	0.0018 (12)	0.0041 (12)	0.0038 (12)
N21	0.0235 (12)	0.0151 (11)	0.0398 (13)	−0.0027 (11)	0.0119 (13)	−0.0061 (11)
N3	0.0186 (12)	0.0149 (11)	0.0205 (10)	0.0010 (10)	0.0022 (9)	−0.0026 (10)
C4	0.0180 (14)	0.0135 (14)	0.0161 (12)	−0.0005 (13)	−0.0027 (11)	−0.0022 (12)
C5	0.0165 (13)	0.0163 (13)	0.0139 (12)	0.0017 (13)	−0.0013 (13)	0.0016 (11)
C6	0.0162 (14)	0.0147 (14)	0.0162 (12)	−0.0011 (11)	−0.0027 (11)	0.0034 (11)
Cl6	0.0237 (4)	0.0184 (4)	0.0285 (3)	−0.0060 (3)	0.0020 (3)	−0.0042 (3)
N7	0.0194 (12)	0.0205 (12)	0.0187 (12)	−0.0003 (9)	0.0018 (10)	0.0003 (10)
C8	0.0217 (14)	0.0234 (15)	0.0197 (13)	0.0019 (12)	0.0039 (13)	−0.0011 (11)
N9	0.0206 (12)	0.0141 (11)	0.0200 (12)	−0.0031 (10)	0.0042 (10)	−0.0044 (10)

Geometric parameters (Å, º)

N1—C6	1.313 (3)	C4—C5	1.396 (3)
N1—C2	1.375 (3)	C5—C6	1.380 (3)
C2—N21	1.339 (3)	C5—N7	1.388 (3)
C2—N3	1.357 (3)	C6—Cl6	1.732 (3)
N21—H21	0.88	N7—C8	1.310 (3)
N21—H22	0.88	C8—N9	1.368 (3)
N3—C4	1.334 (3)	C8—H8	0.95
C4—N9	1.358 (3)	N9—H9	0.88
C6—N1—C2	117.1 (2)	C6—C5—C4	114.5 (2)
N21—C2—N3	117.7 (2)	N7—C5—C4	110.6 (2)
N21—C2—N1	116.1 (2)	N1—C6—C5	122.9 (2)
N3—C2—N1	126.2 (2)	N1—C6—Cl6	116.75 (18)
C2—N21—H21	120.0	C5—C6—Cl6	120.31 (19)
C2—N21—H22	120.0	C8—N7—C5	103.2 (2)
H21—N21—H22	120.0	N7—C8—N9	114.3 (2)
C4—N3—C2	112.3 (2)	N7—C8—H8	122.8
N3—C4—N9	127.4 (2)	N9—C8—H8	122.8
N3—C4—C5	126.9 (2)	C4—N9—C8	106.17 (19)
N9—C4—C5	105.7 (2)	C4—N9—H9	126.9
C6—C5—N7	134.8 (2)	C8—N9—H9	126.9
C6—N1—C2—N21	179.7 (2)	C2—N1—C6—Cl6	178.67 (16)
C6—N1—C2—N3	−0.5 (4)	N7—C5—C6—N1	179.5 (2)
N21—C2—N3—C4	−179.8 (2)	C4—C5—C6—N1	1.0 (3)
N1—C2—N3—C4	0.4 (3)	N7—C5—C6—Cl6	0.6 (4)
C2—N3—C4—N9	−179.1 (2)	C4—C5—C6—Cl6	−177.89 (18)
C2—N3—C4—C5	0.5 (3)	C6—C5—N7—C8	−178.5 (3)
N3—C4—C5—C6	−1.2 (4)	C4—C5—N7—C8	0.0 (3)
N9—C4—C5—C6	178.52 (19)	C5—N7—C8—N9	0.4 (3)
N3—C4—C5—N7	180.0 (2)	N3—C4—N9—C8	−179.8 (2)
N9—C4—C5—N7	−0.3 (3)	C5—C4—N9—C8	0.5 (3)
C2—N1—C6—C5	−0.3 (3)	N7—C8—N9—C4	−0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···N1^i	0.88	2.22	3.019 (3)	150
N21—H22···N3^ii	0.88	2.15	3.027 (3)	174
N9—H9···N7^iii	0.88	2.02	2.888 (3)	168

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/4; (ii) −x+1/2, y+1/2, −z+1/4; (iii) y, x−1, −z.

(II) 2-amino-6-(4-chlorophenylthio)purine hemihydrate

Crystal data

C11H8ClN5S·0.5H2O	F(000) = 2352
Mr = 286.74	Dx = 1.556 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.353 (3) Å	Cell parameters from 11629 reflections
b = 7.743 (2) Å	θ = 2.9–27.5°
c = 47.60 (1) Å	µ = 0.48 mm^−1
β = 95.85 (3)°	T = 120 K
V = 4896 (2) Å^3	Plate, colourless
Z = 16	0.20 × 0.16 × 0.05 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer	3842 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	3045 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 9.091 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
ϕ and ω scans	h = −15→15
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −9→9
Tmin = 0.737, Tmax = 0.982	l = −56→56
10871 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.058P)^2] where P = (Fo^2 + 2Fc^2)/3
3842 reflections	(Δ/σ)max < 0.001
342 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.57 e Å^−3

Special details

Geometry. Mean plane data ex SHELXL97 for molecule (II) #############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

− 7.2128 (0.0109) x + 6.3182 (0.0051) y + 12.3729 (0.0406) z = 4.8904 (0.0125)

* −0.0080 (0.0014) N1A * 0.0158 (0.0015) C2A * −0.0057 (0.0014) N3A * −0.0107 (0.0015) C4A * 0.0169 (0.0016) C5A * −0.0082 (0.0015) C6A

Rms deviation of fitted atoms = 0.0117

7.3492 (0.0116) x + 6.1911 (0.0057) y − 14.0546 (0.0466) z = 1.6649 (0.0105)

Angle to previous plane (with approximate e.s.d.) = 72.21 (0.06)

* 0.0028 (0.0017) C61A * 0.0027 (0.0018) C62A * −0.0058 (0.0018) C63A * 0.0034 (0.0017) C64A * 0.0022 (0.0017) C65A * −0.0053 (0.0017) C66A

Rms deviation of fitted atoms = 0.0040

6.5943 (0.0111) x + 0.3491 (0.0077) y − 43.5118 (0.0287) z = 0.5136 (0.0079)

Angle to previous plane (with approximate e.s.d.) = 58.89 (0.09)

* 0.0105 (0.0015) N1B * −0.0237 (0.0016) C2B * 0.0089 (0.0015) N3B * 0.0170 (0.0016) C4B * −0.0273 (0.0017) C5B * 0.0147 (0.0016) C6B

Rms deviation of fitted atoms = 0.0183

5.9714 (0.0120) x + 6.8892 (0.0049) y + 2.1861 (0.0471) z = 1.5122 (0.0037)

Angle to previous plane (with approximate e.s.d.) = 79.57 (0.08)

* 0.0026 (0.0016) C61B * 0.0017 (0.0017) C62B * −0.0034 (0.0017) C63B * 0.0008 (0.0017) C64B * 0.0036 (0.0017) C65B * −0.0053 (0.0017) C66B

Rms deviation of fitted atoms = 0.0032

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.11719 (14)	0.3707 (2)	0.27365 (4)	0.0144 (5)
C2A	0.07470 (18)	0.2850 (3)	0.29454 (5)	0.0146 (5)
N21A	−0.01316 (14)	0.2067 (2)	0.28637 (4)	0.0193 (5)
H21A	−0.0445	0.1484	0.2987	0.024*
H22A	−0.0394	0.2138	0.2687	0.024*
N3A	0.11255 (14)	0.2713 (2)	0.32189 (4)	0.0143 (5)
C4A	0.19913 (17)	0.3582 (3)	0.32754 (5)	0.0138 (5)
C5A	0.24720 (18)	0.4550 (3)	0.30837 (5)	0.0137 (5)
C6A	0.20279 (18)	0.4547 (3)	0.28061 (5)	0.0147 (5)
N7A	0.33602 (14)	0.5279 (2)	0.32141 (4)	0.0177 (5)
C8A	0.33918 (18)	0.4728 (3)	0.34752 (5)	0.0175 (6)
H8A	0.3924	0.5002	0.3616	0.022*
N9A	0.25868 (14)	0.3718 (2)	0.35263 (4)	0.0157 (5)
H9A	0.2475	0.3249	0.3689	0.020*
S6A	0.26779 (5)	0.56315 (9)	0.255617 (13)	0.0240 (2)
C61A	0.18479 (19)	0.5587 (3)	0.22408 (5)	0.0191 (6)
C62A	0.0977 (2)	0.6560 (4)	0.22137 (6)	0.0258 (7)
H62A	0.0777	0.7166	0.2372	0.032*
C63A	0.0391 (2)	0.6656 (4)	0.19560 (6)	0.0269 (7)
H63A	−0.0214	0.7311	0.1936	0.034*
C64A	0.0710 (2)	0.5776 (3)	0.17283 (5)	0.0222 (6)
Cl6A	0.00034 (5)	0.59529 (9)	0.139897 (15)	0.0340 (2)
C65A	0.1571 (2)	0.4801 (3)	0.17500 (5)	0.0246 (6)
H65A	0.1772	0.4206	0.1590	0.031*
C66A	0.2140 (2)	0.4701 (3)	0.20089 (5)	0.0225 (6)
H66A	0.2735	0.4021	0.2028	0.028*
N1B	0.52614 (15)	0.1031 (2)	0.06852 (4)	0.0155 (5)
C2B	0.59473 (19)	0.2186 (3)	0.08063 (5)	0.0159 (6)
N21B	0.56467 (16)	0.3853 (2)	0.07955 (4)	0.0220 (5)
H21B	0.6049	0.4665	0.0871	0.027*
H22B	0.5049	0.4127	0.0713	0.027*
N3B	0.68703 (15)	0.1850 (2)	0.09360 (4)	0.0160 (5)
C4B	0.70584 (18)	0.0145 (3)	0.09489 (5)	0.0165 (6)
C5B	0.64082 (19)	−0.1162 (3)	0.08501 (5)	0.0170 (6)
C6B	0.54950 (18)	−0.0639 (3)	0.07062 (5)	0.0155 (6)
N7B	0.68496 (16)	−0.2783 (2)	0.09055 (5)	0.0224 (5)
C8B	0.7737 (2)	−0.2395 (3)	0.10299 (6)	0.0285 (7)
H8B	0.8222	−0.3247	0.1092	0.036*
N9B	0.79129 (16)	−0.0658 (2)	0.10637 (5)	0.0230 (5)
H9B	0.8464	−0.0164	0.1143	0.029*
S6B	0.46857 (5)	−0.22657 (8)	0.055773 (15)	0.02315 (19)
C61B	0.37448 (18)	−0.1154 (3)	0.03378 (5)	0.0183 (6)
C62B	0.38038 (19)	−0.1115 (3)	0.00479 (6)	0.0225 (6)
H62B	0.4376	−0.1582	−0.0028	0.028*
C63B	0.3026 (2)	−0.0392 (3)	−0.01301 (6)	0.0234 (6)
H63B	0.3059	−0.0366	−0.0329	0.029*
C64B	0.22071 (18)	0.0288 (3)	−0.00147 (5)	0.0205 (6)
Cl6B	0.12372 (5)	0.12240 (8)	−0.023529 (15)	0.0320 (2)
C65B	0.21377 (19)	0.0261 (3)	0.02730 (5)	0.0214 (6)
H65B	0.1568	0.0742	0.0349	0.027*
C66B	0.29051 (19)	−0.0473 (3)	0.04489 (5)	0.0205 (6)
H66B	0.2861	−0.0514	0.0647	0.026*
O1W	0.44835 (14)	0.6389 (3)	0.12886 (5)	0.0242 (5)
H1W	0.461 (2)	0.725 (4)	0.1192 (7)	0.051 (11)*
H2W	0.433 (3)	0.685 (4)	0.1441 (8)	0.063 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0128 (11)	0.0174 (11)	0.0126 (11)	−0.0008 (9)	−0.0002 (9)	0.0013 (9)
C2A	0.0135 (13)	0.0176 (13)	0.0126 (13)	0.0017 (11)	0.0005 (11)	−0.0018 (10)
N21A	0.0184 (12)	0.0303 (12)	0.0085 (11)	−0.0108 (10)	−0.0019 (9)	0.0007 (9)
N3A	0.0152 (11)	0.0182 (11)	0.0090 (11)	−0.0006 (9)	−0.0013 (9)	0.0030 (8)
C4A	0.0132 (13)	0.0163 (13)	0.0111 (13)	0.0023 (11)	−0.0022 (11)	−0.0014 (10)
C5A	0.0143 (13)	0.0154 (13)	0.0108 (13)	−0.0017 (10)	−0.0021 (11)	0.0011 (10)
C6A	0.0164 (14)	0.0161 (13)	0.0113 (13)	−0.0001 (11)	−0.0006 (11)	0.0012 (10)
N7A	0.0170 (12)	0.0237 (12)	0.0113 (11)	−0.0057 (10)	−0.0043 (9)	−0.0004 (9)
C8A	0.0163 (14)	0.0207 (14)	0.0144 (14)	−0.0005 (11)	−0.0039 (11)	−0.0012 (10)
N9A	0.0189 (12)	0.0191 (11)	0.0079 (11)	−0.0042 (9)	−0.0041 (9)	0.0036 (8)
S6A	0.0218 (4)	0.0387 (4)	0.0101 (3)	−0.0132 (3)	−0.0048 (3)	0.0070 (3)
C61A	0.0194 (15)	0.0258 (14)	0.0107 (14)	−0.0115 (12)	−0.0047 (11)	0.0051 (10)
C62A	0.0243 (16)	0.0357 (16)	0.0167 (15)	−0.0072 (13)	−0.0014 (12)	−0.0010 (12)
C63A	0.0183 (15)	0.0351 (16)	0.0263 (17)	−0.0014 (13)	−0.0022 (13)	0.0075 (13)
C64A	0.0241 (16)	0.0285 (15)	0.0123 (14)	−0.0105 (13)	−0.0068 (12)	0.0075 (11)
Cl6A	0.0325 (4)	0.0505 (5)	0.0162 (4)	−0.0095 (3)	−0.0114 (3)	0.0109 (3)
C65A	0.0298 (16)	0.0299 (15)	0.0134 (14)	−0.0035 (13)	−0.0018 (12)	0.0008 (11)
C66A	0.0236 (15)	0.0274 (15)	0.0155 (14)	−0.0040 (12)	−0.0039 (12)	0.0055 (11)
N1B	0.0181 (12)	0.0135 (11)	0.0139 (12)	0.0035 (9)	−0.0036 (9)	−0.0011 (8)
C2B	0.0229 (15)	0.0161 (13)	0.0081 (13)	−0.0017 (11)	−0.0016 (11)	−0.0017 (10)
N21B	0.0249 (13)	0.0151 (11)	0.0233 (13)	0.0017 (10)	−0.0108 (10)	−0.0025 (9)
N3B	0.0198 (12)	0.0152 (11)	0.0119 (11)	0.0031 (9)	−0.0041 (9)	−0.0002 (8)
C4B	0.0201 (15)	0.0199 (14)	0.0084 (13)	0.0017 (12)	−0.0037 (11)	−0.0015 (10)
C5B	0.0226 (15)	0.0169 (13)	0.0107 (13)	0.0023 (12)	−0.0024 (11)	−0.0022 (10)
C6B	0.0179 (14)	0.0197 (14)	0.0086 (13)	−0.0008 (11)	−0.0006 (11)	−0.0017 (10)
N7B	0.0252 (13)	0.0167 (11)	0.0228 (13)	0.0058 (10)	−0.0089 (10)	−0.0011 (9)
C8B	0.0289 (17)	0.0214 (15)	0.0313 (17)	0.0068 (13)	−0.0159 (14)	−0.0044 (12)
N9B	0.0211 (12)	0.0207 (12)	0.0244 (13)	0.0021 (10)	−0.0109 (10)	−0.0051 (9)
S6B	0.0237 (4)	0.0150 (3)	0.0280 (4)	−0.0002 (3)	−0.0110 (3)	−0.0002 (3)
C61B	0.0195 (14)	0.0144 (13)	0.0192 (14)	−0.0030 (11)	−0.0060 (12)	−0.0006 (10)
C62B	0.0215 (15)	0.0221 (14)	0.0240 (16)	−0.0009 (12)	0.0024 (13)	−0.0051 (11)
C63B	0.0323 (17)	0.0242 (15)	0.0126 (14)	−0.0052 (13)	−0.0029 (12)	−0.0009 (11)
C64B	0.0210 (15)	0.0152 (14)	0.0231 (15)	−0.0018 (12)	−0.0085 (12)	0.0010 (11)
Cl6B	0.0354 (4)	0.0274 (4)	0.0283 (4)	0.0020 (3)	−0.0201 (3)	0.0012 (3)
C65B	0.0196 (15)	0.0237 (14)	0.0203 (15)	0.0037 (12)	−0.0006 (12)	−0.0018 (11)
C66B	0.0271 (16)	0.0187 (14)	0.0149 (14)	0.0004 (12)	−0.0010 (12)	0.0002 (10)
O1W	0.0244 (11)	0.0330 (12)	0.0147 (11)	0.0008 (9)	−0.0011 (9)	−0.0041 (10)

Geometric parameters (Å, º)

N1A—C6A	1.328 (3)	N1B—C2B	1.365 (3)
N1A—C2A	1.366 (3)	C2B—N3B	1.346 (3)
C2A—N21A	1.342 (3)	C2B—N21B	1.351 (3)
C2A—N3A	1.352 (3)	N21B—H21B	0.88
N21A—H21A	0.88	N21B—H22B	0.88
N21A—H22A	0.88	N3B—C4B	1.345 (3)
N3A—C4A	1.341 (3)	C4B—N9B	1.364 (3)
C4A—N9A	1.370 (3)	C4B—C5B	1.384 (3)
C4A—C5A	1.388 (3)	C5B—C6B	1.396 (3)
C5A—C6A	1.392 (3)	C5B—N7B	1.400 (3)
C5A—N7A	1.400 (3)	C6B—S6B	1.760 (2)
C6A—S6A	1.756 (2)	N7B—C8B	1.304 (3)
N7A—C8A	1.311 (3)	C8B—N9B	1.372 (3)
C8A—N9A	1.371 (3)	C8B—H8B	0.95
C8A—H8A	0.95	N9B—H9B	0.88
N9A—H9A	0.88	S6B—C61B	1.774 (3)
S6A—C61A	1.773 (3)	C61B—C62B	1.390 (4)
C61A—C62A	1.381 (4)	C61B—C66B	1.391 (3)
C61A—C66A	1.389 (4)	C62B—C63B	1.390 (3)
C62A—C63A	1.388 (4)	C62B—H62B	0.95
C62A—H62A	0.95	C63B—C64B	1.377 (3)
C63A—C64A	1.384 (4)	C63B—H63B	0.95
C63A—H63A	0.95	C64B—C65B	1.382 (3)
C64A—C65A	1.370 (4)	C64B—Cl6B	1.740 (3)
C64A—Cl6A	1.751 (3)	C65B—C66B	1.378 (3)
C65A—C66A	1.383 (3)	C65B—H65B	0.95
C65A—H65A	0.95	C66B—H66B	0.95
C66A—H66A	0.95	O1W—H1W	0.84 (4)
N1B—C6B	1.332 (3)	O1W—H2W	0.85 (4)
C6A—N1A—C2A	117.8 (2)	N3B—C2B—N21B	117.2 (2)
N21A—C2A—N3A	118.3 (2)	N3B—C2B—N1B	127.6 (2)
N21A—C2A—N1A	115.1 (2)	N21B—C2B—N1B	115.2 (2)
N3A—C2A—N1A	126.7 (2)	C2B—N21B—H21B	120.0
C2A—N21A—H21A	120.0	C2B—N21B—H22B	120.0
C2A—N21A—H22A	120.0	H21B—N21B—H22B	120.0
H21A—N21A—H22A	120.0	C4B—N3B—C2B	111.64 (19)
C4A—N3A—C2A	112.6 (2)	N3B—C4B—N9B	127.7 (2)
N3A—C4A—N9A	128.7 (2)	N3B—C4B—C5B	126.5 (2)
N3A—C4A—C5A	125.9 (2)	N9B—C4B—C5B	105.9 (2)
N9A—C4A—C5A	105.4 (2)	C4B—C5B—C6B	116.2 (2)
C4A—C5A—C6A	116.3 (2)	C4B—C5B—N7B	110.7 (2)
C4A—C5A—N7A	110.7 (2)	C6B—C5B—N7B	133.0 (2)
C6A—C5A—N7A	132.9 (2)	N1B—C6B—C5B	120.3 (2)
N1A—C6A—C5A	120.7 (2)	N1B—C6B—S6B	122.37 (18)
N1A—C6A—S6A	122.53 (18)	C5B—C6B—S6B	117.32 (18)
C5A—C6A—S6A	116.75 (18)	C8B—N7B—C5B	103.0 (2)
C8A—N7A—C5A	103.48 (19)	N7B—C8B—N9B	114.6 (2)
N7A—C8A—N9A	113.8 (2)	N7B—C8B—H8B	122.7
N7A—C8A—H8A	123.1	N9B—C8B—H8B	122.7
N9A—C8A—H8A	123.1	C4B—N9B—C8B	105.9 (2)
C4A—N9A—C8A	106.56 (19)	C4B—N9B—H9B	127.1
C4A—N9A—H9A	126.7	C8B—N9B—H9B	127.1
C8A—N9A—H9A	126.7	C6B—S6B—C61B	104.99 (11)
C6A—S6A—C61A	104.76 (11)	C62B—C61B—C66B	119.9 (2)
C62A—C61A—C66A	119.8 (2)	C62B—C61B—S6B	119.21 (19)
C62A—C61A—S6A	121.1 (2)	C66B—C61B—S6B	120.6 (2)
C66A—C61A—S6A	118.7 (2)	C63B—C62B—C61B	120.0 (2)
C61A—C62A—C63A	120.4 (3)	C63B—C62B—H62B	120.0
C61A—C62A—H62A	119.8	C61B—C62B—H62B	120.0
C63A—C62A—H62A	119.8	C64B—C63B—C62B	119.0 (2)
C64A—C63A—C62A	118.4 (3)	C64B—C63B—H63B	120.5
C64A—C63A—H63A	120.8	C62B—C63B—H63B	120.5
C62A—C63A—H63A	120.8	C63B—C64B—C65B	121.7 (2)
C65A—C64A—C63A	122.4 (2)	C63B—C64B—Cl6B	119.4 (2)
C65A—C64A—Cl6A	118.8 (2)	C65B—C64B—Cl6B	118.9 (2)
C63A—C64A—Cl6A	118.8 (2)	C66B—C65B—C64B	119.2 (2)
C64A—C65A—C66A	118.6 (3)	C66B—C65B—H65B	120.4
C64A—C65A—H65A	120.7	C64B—C65B—H65B	120.4
C66A—C65A—H65A	120.7	C65B—C66B—C61B	120.3 (2)
C65A—C66A—C61A	120.5 (3)	C65B—C66B—H66B	119.9
C65A—C66A—H66A	119.7	C61B—C66B—H66B	119.9
C61A—C66A—H66A	119.7	H1W—O1W—H2W	102 (3)
C6B—N1B—C2B	117.6 (2)
C6A—N1A—C2A—N21A	178.16 (19)	C6B—N1B—C2B—N3B	3.4 (4)
C6A—N1A—C2A—N3A	−2.4 (3)	C6B—N1B—C2B—N21B	−175.8 (2)
N21A—C2A—N3A—C4A	−178.5 (2)	N21B—C2B—N3B—C4B	176.1 (2)
N1A—C2A—N3A—C4A	2.1 (3)	N1B—C2B—N3B—C4B	−3.1 (3)
C2A—N3A—C4A—N9A	−179.3 (2)	C2B—N3B—C4B—N9B	179.7 (2)
C2A—N3A—C4A—C5A	0.7 (3)	C2B—N3B—C4B—C5B	−1.2 (3)
N3A—C4A—C5A—C6A	−2.8 (3)	N3B—C4B—C5B—C6B	4.6 (4)
N9A—C4A—C5A—C6A	177.2 (2)	N9B—C4B—C5B—C6B	−176.1 (2)
N3A—C4A—C5A—N7A	−179.8 (2)	N3B—C4B—C5B—N7B	−178.6 (2)
N9A—C4A—C5A—N7A	0.1 (3)	N9B—C4B—C5B—N7B	0.7 (3)
C2A—N1A—C6A—C5A	−0.1 (3)	C2B—N1B—C6B—C5B	0.6 (3)
C2A—N1A—C6A—S6A	177.53 (17)	C2B—N1B—C6B—S6B	−179.50 (17)
C4A—C5A—C6A—N1A	2.4 (3)	C4B—C5B—C6B—N1B	−4.1 (3)
N7A—C5A—C6A—N1A	178.6 (2)	N7B—C5B—C6B—N1B	−180.0 (2)
C4A—C5A—C6A—S6A	−175.34 (17)	C4B—C5B—C6B—S6B	175.96 (18)
N7A—C5A—C6A—S6A	0.9 (4)	N7B—C5B—C6B—S6B	0.1 (4)
C4A—C5A—N7A—C8A	0.5 (3)	C4B—C5B—N7B—C8B	−0.8 (3)
C6A—C5A—N7A—C8A	−175.9 (3)	C6B—C5B—N7B—C8B	175.2 (3)
C5A—N7A—C8A—N9A	−0.9 (3)	C5B—N7B—C8B—N9B	0.6 (3)
N3A—C4A—N9A—C8A	179.3 (2)	N3B—C4B—N9B—C8B	179.0 (2)
C5A—C4A—N9A—C8A	−0.7 (2)	C5B—C4B—N9B—C8B	−0.3 (3)
N7A—C8A—N9A—C4A	1.0 (3)	N7B—C8B—N9B—C4B	−0.3 (3)
N1A—C6A—S6A—C61A	8.8 (2)	N1B—C6B—S6B—C61B	11.2 (2)
C5A—C6A—S6A—C61A	−173.52 (19)	C5B—C6B—S6B—C61B	−168.85 (19)
C6A—S6A—C61A—C62A	70.4 (2)	C6B—S6B—C61B—C62B	101.1 (2)
C6A—S6A—C61A—C66A	−116.5 (2)	C6B—S6B—C61B—C66B	−85.2 (2)
C66A—C61A—C62A—C63A	0.0 (4)	C66B—C61B—C62B—C63B	0.2 (4)
S6A—C61A—C62A—C63A	173.1 (2)	S6B—C61B—C62B—C63B	173.98 (18)
C61A—C62A—C63A—C64A	−0.8 (4)	C61B—C62B—C63B—C64B	0.4 (4)
C62A—C63A—C64A—C65A	0.9 (4)	C62B—C63B—C64B—C65B	−0.3 (4)
C62A—C63A—C64A—Cl6A	−177.61 (19)	C62B—C63B—C64B—Cl6B	179.09 (18)
C63A—C64A—C65A—C66A	−0.2 (4)	C63B—C64B—C65B—C66B	−0.3 (4)
Cl6A—C64A—C65A—C66A	178.36 (19)	Cl6B—C64B—C65B—C66B	−179.76 (18)
C64A—C65A—C66A—C61A	−0.7 (4)	C64B—C65B—C66B—C61B	0.9 (4)
C62A—C61A—C66A—C65A	0.8 (4)	C62B—C61B—C66B—C65B	−0.8 (4)
S6A—C61A—C66A—C65A	−172.45 (19)	S6B—C61B—C66B—C65B	−174.56 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N7A^i	0.88	2.22	3.072 (3)	163
N21A—H22A···N1A^ii	0.88	2.49	3.300 (3)	154
N21A—H22A···S6A^i	0.88	2.84	3.326 (2)	117
N9A—H9A···N3B^iii	0.88	2.19	2.965 (3)	146
N21B—H21B···N7B^iv	0.88	2.25	3.077 (3)	158
N21B—H22B···Cl6B^v	0.88	2.72	3.475 (2)	145
N21B—H22B···S6B^iv	0.88	2.92	3.415 (2)	118
N9B—H9B···O1W^vi	0.88	1.89	2.757 (3)	166
O1W—H1W···S6B^iv	0.84 (4)	3.05 (4)	3.668 (2)	132 (3)
O1W—H2W···N3A^vii	0.85 (4)	1.91 (4)	2.756 (3)	174 (3)

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

(III) 2-amino-6-(4-methylphenylthio)purine 1/3hydrate

Crystal data

C12H11N5S·0.333H2O	Z = 6
Mr = 263.32	F(000) = 824
Triclinic, P1	Dx = 1.389 Mg m^−3
a = 10.8074 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6355 (3) Å	Cell parameters from 40289 reflections
c = 15.3922 (3) Å	θ = 2.9–27.5°
α = 85.468 (2)°	µ = 0.25 mm^−1
β = 83.265 (1)°	T = 150 K
γ = 79.7992 (9)°	Plate, colourless
V = 1888.46 (7) Å^3	0.12 × 0.12 × 0.01 mm

Data collection

Bruker–Nonius KappaCCD area detector diffractometer	8568 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	4357 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.111
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ϕ and ω scans	h = −14→14
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −15→15
Tmin = 0.931, Tmax = 0.998	l = −19→19
36016 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0537P)^2] where P = (Fo^2 + 2Fc^2)/3
8568 reflections	(Δ/σ)max < 0.001
507 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Geometry. Mean plane data ex SHELXL97 for molecule (III) ##############################################

10.4927 (0.0026) x + 4.6335 (0.0105) y + 2.9885 (0.0160) z = 6.7844 (0.0093)

* 0.0052 (0.0017) N1A * −0.0075 (0.0018) C2A * 0.0048 (0.0017) N3A * −0.0014 (0.0018) C4A * −0.0004 (0.0018) C5A * −0.0007 (0.0018) C6A

Rms deviation of fitted atoms = 0.0043

− 5.4722 (0.0101) x + 7.4941 (0.0096) y + 6.3778 (0.0145) z = 6.0185 (0.0099)

Angle to previous plane (with approximate e.s.d.) = 73.08 (0.07)

* 0.0062 (0.0018) C61A * −0.0105 (0.0018) C62A * 0.0045 (0.0019) C63A * 0.0061 (0.0020) C64A * −0.0107 (0.0019) C65A * 0.0044 (0.0019) C66A

Rms deviation of fitted atoms = 0.0075

6.0317 (0.0082) x − 6.9901 (0.0085) y − 6.1715 (0.0143) z = 0.8298 (0.0063)

Angle to previous plane (with approximate e.s.d.) = 3.58 (0.17)

* −0.0083 (0.0016) N1B * 0.0115 (0.0017) C2B * 0.0013 (0.0016) N3B * −0.0164 (0.0017) C4B * 0.0180 (0.0017) C5B * −0.0061 (0.0017) C6B

Rms deviation of fitted atoms = 0.0118

7.2341 (0.0091) x + 4.8210 (0.0120) y − 8.8851 (0.0140) z = 1.7212 (0.0017)

Angle to previous plane (with approximate e.s.d.) = 63.21 (0.08)

* 0.0129 (0.0019) C61B * 0.0009 (0.0019) C62B * −0.0136 (0.0020) C63B * 0.0124 (0.0020) C64B * 0.0014 (0.0021) C65B * −0.0140 (0.0020) C66B

Rms deviation of fitted atoms = 0.0109

− 3.3624 (0.0097) x + 8.8480 (0.0067) y + 7.2945 (0.0131) z = 4.4083 (0.0057)

Angle to previous plane (with approximate e.s.d.) = 74.01 (0.08)

* −0.0312 (0.0016) N1C * 0.0498 (0.0016) C2C * −0.0161 (0.0016) N3C * −0.0317 (0.0016) C4C * 0.0449 (0.0017) C5C * −0.0157 (0.0017) C6C

Rms deviation of fitted atoms = 0.0341

9.4416 (0.0076) x + 7.3141 (0.0126) y + 3.0886 (0.0192) z = 3.3833 (0.0088)

Angle to previous plane (with approximate e.s.d.) = 80.80 (0.08)

* −0.0007 (0.0021) C61C * −0.0085 (0.0024) C62C * 0.0135 (0.0025) C63C * −0.0092 (0.0022) C64C * 0.0001 (0.0023) C65C * 0.0048 (0.0023) C66C

Rms deviation of fitted atoms = 0.0078

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.3642 (2)	0.30213 (19)	0.52465 (12)	0.0301 (5)
C2A	0.4158 (3)	0.1868 (2)	0.51806 (16)	0.0309 (7)
N21A	0.4572 (2)	0.1529 (2)	0.43641 (13)	0.0461 (7)
H21A	0.4942	0.0802	0.4285	0.058*
H22A	0.4472	0.2034	0.3911	0.058*
N3A	0.4344 (2)	0.10474 (18)	0.58421 (12)	0.0297 (5)
C4A	0.3377 (2)	0.2620 (2)	0.67783 (15)	0.0270 (6)
C5A	0.3924 (2)	0.1484 (2)	0.66205 (15)	0.0268 (6)
C6A	0.3248 (2)	0.3389 (2)	0.60420 (15)	0.0278 (6)
N7A	0.3079 (2)	0.2750 (2)	0.76790 (13)	0.0341 (6)
C8A	0.3435 (3)	0.1697 (2)	0.80220 (16)	0.0351 (7)
H8A	0.3343	0.1507	0.8635	0.044*
N9A	0.3949 (2)	0.08953 (19)	0.74260 (12)	0.0317 (6)
H9A	0.4239	0.0149	0.7536	0.040*
S6A	0.25434 (8)	0.48439 (7)	0.62075 (4)	0.0422 (2)
C61A	0.2540 (3)	0.5521 (2)	0.51377 (16)	0.0309 (7)
C62A	0.1672 (3)	0.5339 (2)	0.45815 (18)	0.0372 (7)
H62A	0.1135	0.4778	0.4746	0.046*
C63A	0.1601 (3)	0.5983 (3)	0.37874 (18)	0.0429 (8)
H63A	0.0996	0.5871	0.3415	0.054*
C64A	0.2397 (3)	0.6788 (3)	0.35270 (18)	0.0437 (8)
C65A	0.3269 (3)	0.6929 (3)	0.40822 (18)	0.0435 (8)
H65A	0.3836	0.7462	0.3908	0.054*
C66A	0.3332 (3)	0.6317 (2)	0.48803 (17)	0.0381 (7)
H66A	0.3926	0.6443	0.5256	0.048*
C67A	0.2325 (4)	0.7479 (3)	0.26553 (19)	0.0715 (12)
H67A	0.3154	0.7347	0.2311	0.089*
H68A	0.2076	0.8314	0.2754	0.089*
H69A	0.1698	0.7226	0.2336	0.089*
N1B	0.4174 (2)	0.23536 (19)	0.00824 (13)	0.0304 (5)
C2B	0.4887 (2)	0.3190 (2)	−0.02002 (16)	0.0283 (6)
N21B	0.4712 (2)	0.3682 (2)	−0.10040 (13)	0.0369 (6)
H21B	0.5148	0.4225	−0.1229	0.046*
H22B	0.4161	0.3462	−0.1306	0.046*
N3B	0.57405 (19)	0.35560 (19)	0.02360 (12)	0.0284 (5)
C4B	0.5849 (2)	0.2979 (2)	0.10239 (15)	0.0285 (6)
C5B	0.5216 (3)	0.2087 (2)	0.13611 (15)	0.0294 (6)
C6B	0.4335 (2)	0.1803 (2)	0.08603 (16)	0.0297 (6)
N7B	0.5603 (2)	0.16558 (19)	0.21780 (13)	0.0332 (6)
C8B	0.6418 (3)	0.2321 (2)	0.23028 (16)	0.0355 (7)
H8B	0.6838	0.2245	0.2818	0.044*
N9B	0.6616 (2)	0.31325 (19)	0.16328 (12)	0.0305 (5)
H9B	0.7131	0.3646	0.1601	0.038*
S6B	0.34445 (8)	0.07289 (7)	0.12837 (4)	0.0439 (2)
C61B	0.2487 (3)	0.0670 (3)	0.04367 (17)	0.0353 (7)
C62B	0.2625 (3)	−0.0346 (2)	0.00110 (17)	0.0373 (7)
H62B	0.3244	−0.0996	0.0161	0.047*
C63B	0.1858 (3)	−0.0423 (3)	−0.06389 (18)	0.0410 (8)
H63B	0.1946	−0.1135	−0.0922	0.051*
C64B	0.0972 (3)	0.0517 (3)	−0.08792 (18)	0.0429 (8)
C65B	0.0832 (3)	0.1529 (3)	−0.0431 (2)	0.0471 (8)
H65B	0.0217	0.2182	−0.0582	0.059*
C66B	0.1569 (3)	0.1607 (3)	0.02277 (18)	0.0446 (8)
H66B	0.1446	0.2300	0.0537	0.056*
C67B	0.0196 (3)	0.0451 (3)	−0.1620 (2)	0.0620 (10)
H67B	0.0525	0.0885	−0.2142	0.077*
H68B	−0.0686	0.0795	−0.1451	0.077*
H69B	0.0246	−0.0368	−0.1747	0.077*
N1C	0.2602 (2)	0.34012 (19)	0.30746 (12)	0.0284 (5)
C2C	0.3496 (2)	0.4063 (2)	0.27944 (15)	0.0264 (6)
N21C	0.43612 (19)	0.40878 (18)	0.33629 (12)	0.0297 (5)
H21C	0.4976	0.4494	0.3218	0.037*
H22C	0.4306	0.3698	0.3876	0.037*
N3C	0.36326 (19)	0.46780 (18)	0.20215 (12)	0.0262 (5)
C5C	0.1614 (2)	0.4151 (2)	0.18142 (15)	0.0274 (6)
C4C	0.2662 (2)	0.4675 (2)	0.15567 (15)	0.0263 (6)
C6C	0.1647 (2)	0.3452 (2)	0.25935 (16)	0.0287 (6)
N7C	0.0755 (2)	0.4395 (2)	0.11866 (13)	0.0332 (6)
C8C	0.1322 (3)	0.5028 (2)	0.05819 (16)	0.0334 (7)
H8C	0.0961	0.5328	0.0059	0.042*
N9C	0.2469 (2)	0.52242 (19)	0.07558 (12)	0.0311 (5)
H9C	0.2981	0.5624	0.0421	0.039*
S6C	0.04176 (7)	0.26601 (7)	0.29177 (5)	0.0411 (2)
C61C	0.0948 (2)	0.1781 (2)	0.38371 (16)	0.0308 (7)
C62C	0.1771 (3)	0.0754 (3)	0.37279 (19)	0.0527 (9)
H62C	0.2107	0.0533	0.3155	0.066*
C63C	0.2113 (3)	0.0040 (3)	0.4445 (2)	0.0592 (10)
H63C	0.2712	−0.0655	0.4361	0.074*
C64C	0.1609 (3)	0.0305 (3)	0.52823 (17)	0.0373 (7)
C65C	0.0791 (3)	0.1331 (3)	0.53829 (18)	0.0503 (9)
H65C	0.0444	0.1543	0.5956	0.063*
C66C	0.0454 (3)	0.2074 (3)	0.46688 (17)	0.0488 (9)
H66C	−0.0118	0.2786	0.4755	0.061*
C67C	0.1958 (3)	−0.0524 (3)	0.60574 (19)	0.0558 (9)
H67C	0.2844	−0.0900	0.5952	0.070*
H68C	0.1414	−0.1123	0.6135	0.070*
H69C	0.1842	−0.0086	0.6588	0.070*
O1W	0.8062 (2)	0.4882 (2)	0.15590 (13)	0.0392 (5)
H1W	0.781 (3)	0.553 (3)	0.180 (2)	0.071 (13)*
H2W	0.887 (4)	0.474 (3)	0.149 (2)	0.079 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0435 (14)	0.0225 (14)	0.0236 (11)	−0.0053 (11)	−0.0034 (10)	0.0011 (10)
C2A	0.0438 (18)	0.0223 (17)	0.0262 (14)	−0.0073 (13)	−0.0020 (12)	0.0029 (12)
N21A	0.086 (2)	0.0225 (14)	0.0237 (12)	0.0000 (13)	0.0018 (12)	0.0019 (10)
N3A	0.0431 (14)	0.0227 (13)	0.0226 (11)	−0.0076 (11)	0.0000 (10)	0.0017 (10)
C4A	0.0353 (16)	0.0219 (16)	0.0239 (14)	−0.0084 (13)	0.0006 (11)	−0.0003 (12)
C5A	0.0346 (16)	0.0245 (16)	0.0218 (13)	−0.0085 (13)	−0.0038 (11)	0.0041 (12)
C6A	0.0353 (16)	0.0230 (16)	0.0257 (14)	−0.0076 (13)	−0.0025 (11)	0.0009 (12)
N7A	0.0473 (15)	0.0296 (15)	0.0247 (12)	−0.0088 (12)	0.0003 (10)	0.0008 (11)
C8A	0.0481 (19)	0.0345 (19)	0.0225 (14)	−0.0101 (15)	0.0011 (12)	0.0003 (13)
N9A	0.0510 (15)	0.0213 (13)	0.0225 (11)	−0.0068 (11)	−0.0043 (10)	0.0027 (10)
S6A	0.0659 (6)	0.0264 (4)	0.0287 (4)	0.0017 (4)	0.0025 (3)	−0.0001 (3)
C61A	0.0371 (17)	0.0199 (16)	0.0327 (15)	0.0023 (13)	−0.0031 (13)	−0.0008 (12)
C62A	0.0351 (17)	0.0298 (18)	0.0446 (17)	−0.0005 (14)	0.0008 (13)	−0.0080 (14)
C63A	0.0455 (19)	0.040 (2)	0.0401 (17)	0.0119 (16)	−0.0132 (14)	−0.0122 (15)
C64A	0.065 (2)	0.0263 (18)	0.0324 (16)	0.0109 (17)	−0.0040 (15)	0.0017 (14)
C65A	0.054 (2)	0.0304 (19)	0.0443 (18)	−0.0075 (15)	−0.0010 (15)	0.0063 (15)
C66A	0.0437 (19)	0.0303 (18)	0.0394 (16)	−0.0030 (15)	−0.0099 (14)	0.0033 (14)
C67A	0.107 (3)	0.049 (2)	0.0431 (19)	0.021 (2)	−0.0062 (19)	0.0089 (17)
N1B	0.0396 (14)	0.0244 (14)	0.0274 (12)	−0.0097 (11)	−0.0010 (10)	0.0026 (10)
C2B	0.0323 (16)	0.0240 (16)	0.0269 (14)	−0.0027 (13)	−0.0020 (12)	0.0030 (12)
N21B	0.0465 (15)	0.0390 (15)	0.0298 (12)	−0.0201 (12)	−0.0111 (11)	0.0088 (11)
N3B	0.0341 (13)	0.0271 (13)	0.0233 (11)	−0.0061 (11)	−0.0025 (10)	0.0038 (10)
C4B	0.0364 (16)	0.0230 (16)	0.0238 (14)	0.0007 (13)	−0.0017 (12)	−0.0026 (12)
C5B	0.0416 (17)	0.0219 (16)	0.0216 (13)	−0.0020 (13)	0.0029 (12)	0.0011 (12)
C6B	0.0385 (17)	0.0228 (16)	0.0257 (14)	−0.0044 (13)	0.0032 (12)	0.0002 (12)
N7B	0.0503 (16)	0.0256 (14)	0.0221 (12)	−0.0045 (12)	−0.0032 (10)	0.0036 (10)
C8B	0.0499 (19)	0.0283 (18)	0.0242 (14)	0.0016 (15)	−0.0038 (13)	0.0053 (13)
N9B	0.0386 (14)	0.0271 (14)	0.0251 (11)	−0.0062 (11)	−0.0030 (10)	0.0033 (10)
S6B	0.0622 (6)	0.0410 (5)	0.0315 (4)	−0.0236 (4)	−0.0011 (3)	0.0074 (3)
C61B	0.0367 (17)	0.0308 (18)	0.0377 (16)	−0.0122 (14)	0.0062 (13)	0.0019 (14)
C62B	0.0404 (18)	0.0295 (18)	0.0387 (16)	−0.0038 (14)	0.0051 (13)	−0.0007 (14)
C63B	0.0453 (19)	0.038 (2)	0.0396 (17)	−0.0125 (16)	0.0064 (14)	−0.0080 (14)
C64B	0.0399 (19)	0.048 (2)	0.0394 (17)	−0.0126 (16)	0.0054 (14)	0.0049 (15)
C65B	0.0410 (19)	0.038 (2)	0.056 (2)	0.0024 (16)	0.0024 (15)	0.0023 (16)
C66B	0.053 (2)	0.0325 (19)	0.0460 (18)	−0.0101 (16)	0.0108 (15)	−0.0060 (15)
C67B	0.056 (2)	0.078 (3)	0.051 (2)	−0.016 (2)	−0.0030 (17)	0.0049 (19)
N1C	0.0351 (14)	0.0254 (13)	0.0247 (11)	−0.0066 (11)	−0.0028 (10)	0.0022 (10)
C2C	0.0309 (16)	0.0192 (15)	0.0270 (14)	−0.0003 (13)	−0.0022 (12)	0.0008 (12)
N21C	0.0326 (13)	0.0303 (14)	0.0265 (11)	−0.0077 (11)	−0.0075 (10)	0.0079 (10)
N3C	0.0312 (13)	0.0232 (13)	0.0228 (11)	−0.0020 (10)	−0.0036 (10)	0.0029 (10)
C5C	0.0342 (16)	0.0275 (16)	0.0197 (13)	−0.0030 (13)	−0.0033 (11)	−0.0012 (12)
C4C	0.0327 (16)	0.0232 (16)	0.0209 (13)	−0.0017 (13)	−0.0001 (12)	0.0001 (11)
C6C	0.0375 (17)	0.0226 (16)	0.0258 (14)	−0.0076 (13)	0.0011 (12)	−0.0019 (12)
N7C	0.0390 (14)	0.0375 (15)	0.0241 (11)	−0.0112 (12)	−0.0053 (10)	0.0057 (11)
C8C	0.0387 (18)	0.0364 (18)	0.0261 (14)	−0.0074 (14)	−0.0090 (13)	0.0018 (13)
N9C	0.0356 (14)	0.0353 (15)	0.0222 (11)	−0.0093 (11)	−0.0037 (10)	0.0070 (10)
S6C	0.0444 (5)	0.0433 (5)	0.0381 (4)	−0.0179 (4)	−0.0102 (3)	0.0137 (4)
C61C	0.0340 (16)	0.0266 (17)	0.0329 (15)	−0.0116 (13)	−0.0028 (12)	0.0055 (12)
C62C	0.072 (2)	0.043 (2)	0.0335 (17)	0.0039 (18)	0.0099 (16)	0.0017 (15)
C63C	0.074 (3)	0.039 (2)	0.051 (2)	0.0117 (18)	0.0066 (18)	0.0092 (17)
C64C	0.0374 (17)	0.0355 (19)	0.0402 (17)	−0.0116 (15)	−0.0080 (13)	0.0096 (14)
C65C	0.063 (2)	0.057 (2)	0.0252 (15)	0.0006 (19)	0.0022 (14)	0.0005 (15)
C66C	0.060 (2)	0.041 (2)	0.0366 (17)	0.0110 (17)	−0.0014 (15)	−0.0030 (15)
C67C	0.063 (2)	0.055 (2)	0.0517 (19)	−0.0209 (18)	−0.0159 (17)	0.0226 (17)
O1W	0.0384 (14)	0.0433 (15)	0.0370 (12)	−0.0081 (11)	−0.0034 (10)	−0.0074 (11)

Geometric parameters (Å, º)

N1A—C6A	1.326 (3)	C61B—C62B	1.374 (4)
N1A—C2A	1.366 (3)	C61B—C66B	1.383 (4)
C2A—N3A	1.347 (3)	C62B—C63B	1.389 (4)
C2A—N21A	1.349 (3)	C62B—H62B	0.95
N21A—H21A	0.88	C63B—C64B	1.378 (4)
N21A—H22A	0.88	C63B—H63B	0.95
N3A—C5A	1.337 (3)	C64B—C65B	1.388 (4)
C4A—C5A	1.377 (3)	C64B—C67B	1.506 (4)
C4A—C6A	1.392 (3)	C65B—C66B	1.378 (4)
C4A—N7A	1.400 (3)	C65B—H65B	0.95
C5A—N9A	1.369 (3)	C66B—H66B	0.95
C6A—S6A	1.754 (3)	C67B—H67B	0.98
N7A—C8A	1.306 (3)	C67B—H68B	0.98
C8A—N9A	1.361 (3)	C67B—H69B	0.98
C8A—H8A	0.95	N1C—C6C	1.330 (3)
N9A—H9A	0.88	N1C—C2C	1.351 (3)
S6A—C61A	1.769 (3)	C2C—N3C	1.345 (3)
C61A—C66A	1.375 (4)	C2C—N21C	1.359 (3)
C61A—C62A	1.394 (4)	N21C—H21C	0.88
C62A—C63A	1.385 (4)	N21C—H22C	0.88
C62A—H62A	0.95	N3C—C4C	1.338 (3)
C63A—C64A	1.387 (4)	C5C—C4C	1.383 (4)
C63A—H63A	0.95	C5C—C6C	1.395 (3)
C64A—C65A	1.382 (4)	C5C—N7C	1.396 (3)
C64A—C67A	1.512 (4)	C4C—N9C	1.364 (3)
C65A—C66A	1.373 (4)	C6C—S6C	1.752 (3)
C65A—H65A	0.95	N7C—C8C	1.304 (3)
C66A—H66A	0.95	C8C—N9C	1.359 (3)
C67A—H67A	0.98	C8C—H8C	0.95
C67A—H68A	0.98	N9C—H9C	0.88
C67A—H69A	0.98	S6C—C61C	1.770 (3)
N1B—C6B	1.328 (3)	C61C—C62C	1.366 (4)
N1B—C2B	1.360 (3)	C61C—C66C	1.373 (3)
C2B—N21B	1.341 (3)	C62C—C63C	1.374 (4)
C2B—N3B	1.346 (3)	C62C—H62C	0.95
N21B—H21B	0.88	C63C—C64C	1.375 (4)
N21B—H22B	0.88	C63C—H63C	0.95
N3B—C4B	1.346 (3)	C64C—C65C	1.362 (4)
C4B—N9B	1.363 (3)	C64C—C67C	1.513 (4)
C4B—C5B	1.378 (4)	C65C—C66C	1.386 (4)
C5B—C6B	1.391 (4)	C65C—H65C	0.95
C5B—N7B	1.399 (3)	C66C—H66C	0.95
C6B—S6B	1.750 (3)	C67C—H67C	0.98
N7B—C8B	1.310 (3)	C67C—H68C	0.98
C8B—N9B	1.366 (3)	C67C—H69C	0.98
C8B—H8B	0.95	O1W—H1W	0.85 (4)
N9B—H9B	0.88	O1W—H2W	0.86 (4)
S6B—C61B	1.770 (3)
C6A—N1A—C2A	117.6 (2)	C62B—C61B—C66B	119.8 (3)
N3A—C2A—N21A	116.7 (2)	C62B—C61B—S6B	119.0 (2)
N3A—C2A—N1A	127.2 (2)	C66B—C61B—S6B	121.1 (2)
N21A—C2A—N1A	116.1 (2)	C61B—C62B—C63B	120.0 (3)
C2A—N21A—H21A	120.0	C61B—C62B—H62B	120.0
C2A—N21A—H22A	120.0	C63B—C62B—H62B	120.0
H21A—N21A—H22A	120.0	C64B—C63B—C62B	120.9 (3)
C5A—N3A—C2A	111.6 (2)	C64B—C63B—H63B	119.5
C5A—C4A—C6A	115.9 (2)	C62B—C63B—H63B	119.5
C5A—C4A—N7A	110.6 (2)	C63B—C64B—C65B	118.2 (3)
C6A—C4A—N7A	133.5 (2)	C63B—C64B—C67B	120.7 (3)
N3A—C5A—N9A	127.1 (2)	C65B—C64B—C67B	121.1 (3)
N3A—C5A—C4A	127.1 (2)	C66B—C65B—C64B	121.3 (3)
N9A—C5A—C4A	105.7 (2)	C66B—C65B—H65B	119.3
N1A—C6A—C4A	120.6 (2)	C64B—C65B—H65B	119.3
N1A—C6A—S6A	121.77 (19)	C65B—C66B—C61B	119.7 (3)
C4A—C6A—S6A	117.64 (19)	C65B—C66B—H66B	120.2
C8A—N7A—C4A	103.2 (2)	C61B—C66B—H66B	120.2
N7A—C8A—N9A	114.3 (2)	C64B—C67B—H67B	109.5
N7A—C8A—H8A	122.9	C64B—C67B—H68B	109.5
N9A—C8A—H8A	122.9	H67B—C67B—H68B	109.5
C8A—N9A—C5A	106.2 (2)	C64B—C67B—H69B	109.5
C8A—N9A—H9A	126.9	H67B—C67B—H69B	109.5
C5A—N9A—H9A	126.9	H68B—C67B—H69B	109.5
C6A—S6A—C61A	104.04 (12)	C6C—N1C—C2C	117.9 (2)
C66A—C61A—C62A	119.5 (3)	N3C—C2C—N1C	127.6 (2)
C66A—C61A—S6A	119.2 (2)	N3C—C2C—N21C	117.1 (2)
C62A—C61A—S6A	121.0 (2)	N1C—C2C—N21C	115.3 (2)
C63A—C62A—C61A	119.5 (3)	C2C—N21C—H21C	120.0
C63A—C62A—H62A	120.3	C2C—N21C—H22C	120.0
C61A—C62A—H62A	120.3	H21C—N21C—H22C	120.0
C62A—C63A—C64A	121.1 (3)	C4C—N3C—C2C	111.3 (2)
C62A—C63A—H63A	119.4	C4C—C5C—C6C	116.1 (2)
C64A—C63A—H63A	119.4	C4C—C5C—N7C	110.6 (2)
C65A—C64A—C63A	118.1 (3)	C6C—C5C—N7C	133.2 (3)
C65A—C64A—C67A	121.0 (3)	N3C—C4C—N9C	127.6 (2)
C63A—C64A—C67A	120.9 (3)	N3C—C4C—C5C	126.5 (2)
C66A—C65A—C64A	121.5 (3)	N9C—C4C—C5C	105.8 (2)
C66A—C65A—H65A	119.3	N1C—C6C—C5C	119.7 (2)
C64A—C65A—H65A	119.3	N1C—C6C—S6C	121.4 (2)
C65A—C66A—C61A	120.3 (3)	C5C—C6C—S6C	118.9 (2)
C65A—C66A—H66A	119.9	C8C—N7C—C5C	102.8 (2)
C61A—C66A—H66A	119.9	N7C—C8C—N9C	114.9 (2)
C64A—C67A—H67A	109.5	N7C—C8C—H8C	122.5
C64A—C67A—H68A	109.5	N9C—C8C—H8C	122.5
H67A—C67A—H68A	109.5	C8C—N9C—C4C	105.8 (2)
C64A—C67A—H69A	109.5	C8C—N9C—H9C	127.1
H67A—C67A—H69A	109.5	C4C—N9C—H9C	127.1
H68A—C67A—H69A	109.5	C6C—S6C—C61C	103.13 (12)
C6B—N1B—C2B	118.2 (2)	C62C—C61C—C66C	119.1 (3)
N21B—C2B—N3B	117.8 (2)	C62C—C61C—S6C	120.5 (2)
N21B—C2B—N1B	115.2 (2)	C66C—C61C—S6C	120.1 (2)
N3B—C2B—N1B	126.9 (2)	C61C—C62C—C63C	120.1 (3)
C2B—N21B—H21B	120.0	C61C—C62C—H62C	120.0
C2B—N21B—H22B	120.0	C63C—C62C—H62C	120.0
H21B—N21B—H22B	120.0	C62C—C63C—C64C	121.7 (3)
C4B—N3B—C2B	112.1 (2)	C62C—C63C—H63C	119.1
N3B—C4B—N9B	127.5 (3)	C64C—C63C—H63C	119.1
N3B—C4B—C5B	125.9 (2)	C65C—C64C—C63C	117.6 (3)
N9B—C4B—C5B	106.5 (2)	C65C—C64C—C67C	121.8 (3)
C4B—C5B—C6B	116.8 (2)	C63C—C64C—C67C	120.6 (3)
C4B—C5B—N7B	110.4 (2)	C64C—C65C—C66C	121.5 (3)
C6B—C5B—N7B	132.8 (3)	C64C—C65C—H65C	119.3
N1B—C6B—C5B	119.9 (2)	C66C—C65C—H65C	119.3
N1B—C6B—S6B	121.4 (2)	C61C—C66C—C65C	119.9 (3)
C5B—C6B—S6B	118.67 (19)	C61C—C66C—H66C	120.0
C8B—N7B—C5B	102.9 (2)	C65C—C66C—H66C	120.0
N7B—C8B—N9B	114.7 (2)	C64C—C67C—H67C	109.5
N7B—C8B—H8B	122.7	C64C—C67C—H68C	109.5
N9B—C8B—H8B	122.7	H67C—C67C—H68C	109.5
C4B—N9B—C8B	105.5 (2)	C64C—C67C—H69C	109.5
C4B—N9B—H9B	127.3	H67C—C67C—H69C	109.5
C8B—N9B—H9B	127.3	H68C—C67C—H69C	109.5
C6B—S6B—C61B	102.41 (13)	H1W—O1W—H2W	110 (3)
C6A—N1A—C2A—N3A	−1.6 (4)	C5B—N7B—C8B—N9B	−1.2 (3)
C6A—N1A—C2A—N21A	−178.8 (2)	N3B—C4B—N9B—C8B	−178.0 (2)
N21A—C2A—N3A—C5A	178.6 (2)	C5B—C4B—N9B—C8B	0.5 (3)
N1A—C2A—N3A—C5A	1.5 (4)	N7B—C8B—N9B—C4B	0.5 (3)
C2A—N3A—C5A—N9A	179.2 (3)	N1B—C6B—S6B—C61B	1.0 (2)
C2A—N3A—C5A—C4A	−0.8 (4)	C5B—C6B—S6B—C61B	−179.8 (2)
C6A—C4A—C5A—N3A	0.2 (4)	C6B—S6B—C61B—C62B	116.4 (2)
N7A—C4A—C5A—N3A	−179.0 (2)	C6B—S6B—C61B—C66B	−66.6 (2)
C6A—C4A—C5A—N9A	−179.8 (2)	C66B—C61B—C62B—C63B	1.2 (4)
N7A—C4A—C5A—N9A	1.0 (3)	S6B—C61B—C62B—C63B	178.2 (2)
C2A—N1A—C6A—C4A	0.9 (4)	C61B—C62B—C63B—C64B	1.4 (4)
C2A—N1A—C6A—S6A	−178.8 (2)	C62B—C63B—C64B—C65B	−2.4 (4)
C5A—C4A—C6A—N1A	−0.2 (4)	C62B—C63B—C64B—C67B	176.4 (3)
N7A—C4A—C6A—N1A	178.8 (3)	C63B—C64B—C65B—C66B	1.0 (4)
C5A—C4A—C6A—S6A	179.48 (19)	C67B—C64B—C65B—C66B	−177.9 (3)
N7A—C4A—C6A—S6A	−1.5 (4)	C64B—C65B—C66B—C61B	1.5 (5)
C5A—C4A—N7A—C8A	−1.0 (3)	C62B—C61B—C66B—C65B	−2.6 (4)
C6A—C4A—N7A—C8A	−180.0 (3)	S6B—C61B—C66B—C65B	−179.5 (2)
C4A—N7A—C8A—N9A	0.6 (3)	C6C—N1C—C2C—N3C	−8.8 (4)
N7A—C8A—N9A—C5A	0.0 (3)	C6C—N1C—C2C—N21C	172.2 (2)
N3A—C5A—N9A—C8A	179.4 (2)	N1C—C2C—N3C—C4C	6.9 (3)
C4A—C5A—N9A—C8A	−0.6 (3)	N21C—C2C—N3C—C4C	−174.2 (2)
N1A—C6A—S6A—C61A	0.2 (2)	C2C—N3C—C4C—N9C	178.5 (2)
C4A—C6A—S6A—C61A	−179.5 (2)	C2C—N3C—C4C—C5C	1.7 (4)
C6A—S6A—C61A—C66A	−109.7 (2)	C6C—C5C—C4C—N3C	−7.5 (4)
C6A—S6A—C61A—C62A	76.0 (2)	N7C—C5C—C4C—N3C	175.9 (2)
C66A—C61A—C62A—C63A	−1.6 (4)	C6C—C5C—C4C—N9C	175.1 (2)
S6A—C61A—C62A—C63A	172.8 (2)	N7C—C5C—C4C—N9C	−1.4 (3)
C61A—C62A—C63A—C64A	1.4 (4)	C2C—N1C—C6C—C5C	1.8 (3)
C62A—C63A—C64A—C65A	0.1 (4)	C2C—N1C—C6C—S6C	−178.12 (17)
C62A—C63A—C64A—C67A	179.4 (2)	C4C—C5C—C6C—N1C	5.4 (4)
C63A—C64A—C65A—C66A	−1.6 (4)	N7C—C5C—C6C—N1C	−179.0 (2)
C67A—C64A—C65A—C66A	179.2 (3)	C4C—C5C—C6C—S6C	−174.70 (18)
C64A—C65A—C66A—C61A	1.5 (4)	N7C—C5C—C6C—S6C	0.9 (4)
C62A—C61A—C66A—C65A	0.1 (4)	C4C—C5C—N7C—C8C	1.1 (3)
S6A—C61A—C66A—C65A	−174.3 (2)	C6C—C5C—N7C—C8C	−174.7 (3)
C6B—N1B—C2B—N21B	177.7 (2)	C5C—N7C—C8C—N9C	−0.3 (3)
C6B—N1B—C2B—N3B	−1.7 (4)	N7C—C8C—N9C—C4C	−0.6 (3)
N21B—C2B—N3B—C4B	−178.6 (2)	N3C—C4C—N9C—C8C	−176.1 (2)
N1B—C2B—N3B—C4B	0.7 (4)	C5C—C4C—N9C—C8C	1.2 (3)
C2B—N3B—C4B—N9B	−179.7 (2)	N1C—C6C—S6C—C61C	−7.4 (2)
C2B—N3B—C4B—C5B	2.2 (4)	C5C—C6C—S6C—C61C	172.8 (2)
N3B—C4B—C5B—C6B	−3.8 (4)	C6C—S6C—C61C—C62C	−82.5 (3)
N9B—C4B—C5B—C6B	177.7 (2)	C6C—S6C—C61C—C66C	103.0 (3)
N3B—C4B—C5B—N7B	177.2 (2)	C66C—C61C—C62C—C63C	−1.2 (5)
N9B—C4B—C5B—N7B	−1.2 (3)	S6C—C61C—C62C—C63C	−175.7 (3)
C2B—N1B—C6B—C5B	−0.1 (4)	C61C—C62C—C63C—C64C	2.6 (5)
C2B—N1B—C6B—S6B	179.11 (18)	C62C—C63C—C64C—C65C	−2.6 (5)
C4B—C5B—C6B—N1B	2.6 (4)	C62C—C63C—C64C—C67C	177.2 (3)
N7B—C5B—C6B—N1B	−178.8 (2)	C63C—C64C—C65C—C66C	1.3 (5)
C4B—C5B—C6B—S6B	−176.65 (19)	C67C—C64C—C65C—C66C	−178.6 (3)
N7B—C5B—C6B—S6B	2.0 (4)	C62C—C61C—C66C—C65C	−0.1 (5)
C4B—C5B—N7B—C8B	1.5 (3)	S6C—C61C—C66C—C65C	174.5 (2)
C6B—C5B—N7B—C8B	−177.2 (3)	C64C—C65C—C66C—C61C	0.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N3A^i	0.88	2.17	3.046 (3)	173
N21A—H22A···N21C	0.88	2.46	3.226 (3)	146
N9A—H9A···N7B^i	0.88	2.09	2.948 (3)	164
N21B—H21B···N3C^ii	0.88	2.20	3.062 (3)	168
N21B—H22B···N7A^iii	0.88	2.34	3.204 (3)	168
N9B—H9B···O1W	0.88	1.89	2.765 (3)	173
N21C—H22C···N1A	0.88	2.27	3.130 (3)	164
N21C—H22C···N21A	0.88	2.55	3.226 (3)	134
N9C—H9C···N3B^ii	0.88	1.96	2.833 (3)	174
O1W—H1W···N7A^iv	0.85 (4)	2.23 (4)	3.075 (3)	171 (3)
O1W—H1W···S6A^iv	0.85 (4)	3.05 (3)	3.452 (2)	112 (3)
O1W—H2W···N7C^v	0.86 (4)	2.01 (4)	2.863 (3)	174 (3)

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