Tris(1,10-phenanthroline)sodium 2,4,6-trimercapto-1,3,5-triazin-1-ide

The title compound, [Na(C₁₂H₈N₂)₃](C₃H₂N₃S₃), contains an Na⁺ centre which is ionicly bonded to three 1,10-phenanthroline (phen) ligands and one tri­thio­cyanurate(1−) (ttcH₂) anion. In the crystal structure, the anions are linked via hydrogen bonds to form linear chains. The S and H atoms of the ttcH₂ anion participate in intermolecular N—H...S hydrogen bonding, with N...S distances of 3.298 (2) and 3.336 (2) Å. The phen ligands are almost parallel, with dihedral angles of 3.92 (5), 11.75 (5) and 15.45 (5)°; moreover, they are nearly perpendicular to the ttcH₂ chains, with angles of 81.94 (7), 85.86 (7) and 85.96 (7)°.

S1. Comment

Trithiocyanuric acid (2,4,6-trimercaptotriazine, ttcH₃) and its trisodium salt are very important compounds because they are used for the precipitation of many heavy metals from waste water (Henke et al., 2000; Matlock et al., 2001, 2002). Moreover, the resulting precipitates can be subsequently converted, by increasing the pH of the solution, to useful sulfides and non-toxic cyanuric acid (Bailey et al., 2001). Trithiocyanuric acid also shows antitoxoplasmal activity and it is more effective than 5-fluorouracil and emimicin (Iltzsch & Tankersley, 1994). An important factor in the synthesis of compounds with ttcH₃ is the pH value (Krepps et al., 2001; Cecconi et al., 2003; Mahon et al., 2003). Moreover, up to six atoms of ttcH₃ can be used for coordination to metal centres. Thus miscellaneous types of compounds can be synthesized, which can be mononuclear as well as polynuclear, with the trithiocyanurato anion acting as a bridge. Some structures of complexes of the trithiocyanurate anion with group I and II metals have been published recently, e.g. Li^I (Clegg et al., 1998; Armstrong et al., 2000), Na^I and K^I (Cecconi et al., 2003; Mahon et al., 2003), and Ca^II, Sr^II, Ba^II and Mg^II (Henke & Atwood, 1998; Henke et al., 2001). The title compound,, (I), was prepared as a byproduct during our efforts to synthesize a Mg^II complex with ttcH₃ and 1,10-phenanthroline (phen). \sch

Compound (I) consists of [Na(phen)₃]⁺ and [ttcH₂]⁻ moieties. The Na^I ion is six-coordinated by the N atoms of three phen ligands. The Na—N distances vary from 2.430 (2) to 2.656 (3) Å and compare well with the average length of 2.54 Å for Na—N distances in related compounds in the Cambridge Structural Database (version 5.24.1; Allen, 2002). All the phen ligands are nearly coplanar (the average and maximum deviations of contributing atoms from the least-squares planes are 0.04 and 0.08 Å, respectively) and they are almost parallel. The angles between phen A (atoms N1,···,C14) and phen B (atoms N15,···,C28), phen A and phen C (atoms N29,···,C42), and phen B and phen C are 11.75 (5), 3.92 (5) and 15.45 (5)°, respectively. The average intermolecular distance between phen ligands (A—B, A—C, B—C) in the [Na(phen)₃] units is 3.5 Å [symmetry codes: x + 1/2,1/2 − y,1/2 + z for A—B; x − 1/2,1/2 − y,1/2 + z for A—C].

The six-membered ring of the [ttcH₂]⁻ anion is also almost planar; the average and maximum deviations of contributing atoms from the least-squares planes are 0.04 and 0.06 Å, respectively. The Cremer-Pople puckering parameters (Cremer & Pople, 1975) for the ring are Q = 0.102 (2) Å, θ = 93.0(1.3)° and ϕ₂ = −27.4(1.3)°. Atoms S1 and S2 are significantly shifted from the mean plane through the ring, with displacements of 0.2170 (7) and −0.2280 (7) Å, respectively. The [ttcH₂]⁻ group is almost perpendicular to the phen planes, with angles between ttcH₂ and phen ligands A, B and C of 85.96 (7), 81.94 (7) and 85.86 (7)°, respectively.

In the crystal lattice of (I), the ttcH₂ molecular units are linked into one-dimensional chains by relatively strong intermolecular N—H···S hydrogen bonds.

S2. Experimental

A solution of 1,10-phenanthroline monohydrate (phen·H₂O; 0.4 g, 2 mmol) in ethanol (30 ml) was added to an ethanolic solution (50 ml) of anhydrous magnesium(II) perchlorate (0.22 g, 1 mmol) with stirring at room temperature. The trisodium salt of trithiocyanuric acid nonahydrate (ttcNa₃·9H₂O; 0.4 g, 1 mmol) was dissolved in water (5 ml) and added dropwise to this stirred solution. The solution turned light-yellow in colour and was left for crystallization at ambient temperature. Initially, light-yellow crystals of (I) were obtained after 2 d. These were filtered off, washed with a small amount of ethanol and dried in air. The composition of this compound was proved by X-ray analysis. From the filtrate, a light-yellow precipitate was obtained after 2 d, and the composition of this compound was characterized by elemental analysis (EA1108 CHNS Analyzer, Fisons Instruments, Beverly, Massachusetts, USA) as [Mg(phen)₃](ttcH). The Mg content was determined by chelatometric titration (found: C 63.1, H 3.4, N 16.8, S 12.8, Mg 3.4%; calculated: C 63.3, H 3.4, N 17.0, S 13.0, Mg 3.3%).

S3. Refinement

All H atoms were localized in a differential map of electron density and refined freely.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The molecular structure of (I) (ORTEPIII; Johnson & Burnett, 1996) showing the atom-numbering scheme. Displacement ellipsoids at drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of (I), showing the formation of a chain of [ttcH2]^− and [Na(phen)3]^+ moieties [symmetry codes: (i) 1 − x, −y, 1 − z; (ii) −x, −y, 1 − z; (iii) x + 1/2, 1/2 − y, 1/2 + z; (iv) x − 1/2, 1/2 − y, 1/2 + z].

Tris(1,10-phenanthroline)sodium 2,4,6-trimercapto-1,3,5-triazin-1-ide

Crystal data

[Na(C12H8N2)3](C3H2N3S3)	F(000) = 1528
Mr = 739.86	Dx = 1.434 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5117 reflections
a = 11.1273 (9) Å	θ = 2.5–26.4°
b = 23.8687 (15) Å	µ = 0.28 mm^−1
c = 12.9417 (7) Å	T = 293 K
β = 94.584 (6)°	Prism, yellow
V = 3426.2 (4) Å^3	0.6 × 0.5 × 0.4 mm
Z = 4

Data collection

Kuma KM-4 with CCD area detector diffractometer	5060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Enhance (Oxford Diffraction) monochromator	θmax = 25.0°, θmin = 3.6°
Detector resolution: 16.3 pixels mm^-1	h = −8→13
rotation method, ω scans	k = −28→28
14962 measured reflections	l = −15→15
5915 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	All H-atom parameters refined
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 3.8P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
5915 reflections	Δρmax = 0.25 e Å^−3
574 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (4)

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
S1	0.04604 (7)	0.03936 (3)	0.20068 (5)	0.0493 (2)
S2	0.50057 (6)	−0.00250 (3)	0.33277 (5)	0.04571 (19)
S3	0.16741 (7)	0.00943 (4)	0.59633 (5)	0.0580 (2)
Na	0.60691 (11)	0.23038 (4)	0.16665 (8)	0.0499 (3)
N1	0.6137 (2)	0.30852 (9)	0.28737 (16)	0.0431 (5)
C2	0.6154 (3)	0.36202 (12)	0.2604 (2)	0.0522 (7)
C3	0.6130 (3)	0.40646 (12)	0.3296 (2)	0.0515 (7)
C4	0.6086 (3)	0.39520 (11)	0.4315 (2)	0.0491 (7)
C5	0.6085 (2)	0.33937 (11)	0.4647 (2)	0.0412 (6)
C6	0.6099 (2)	0.29703 (10)	0.38971 (18)	0.0358 (5)
C7	0.6065 (2)	0.23900 (10)	0.42107 (18)	0.0360 (5)
N8	0.6051 (2)	0.19858 (9)	0.34766 (17)	0.0439 (5)
C9	0.5991 (3)	0.14594 (12)	0.3792 (2)	0.0525 (7)
C10	0.5947 (3)	0.12978 (13)	0.4818 (2)	0.0565 (8)
C11	0.5985 (3)	0.17010 (12)	0.5560 (2)	0.0538 (7)
C12	0.6040 (2)	0.22658 (11)	0.52709 (19)	0.0427 (6)
C13	0.6053 (3)	0.27086 (13)	0.6010 (2)	0.0542 (7)
C14	0.6067 (3)	0.32448 (13)	0.5714 (2)	0.0541 (7)
N15	0.7390 (2)	0.26272 (10)	0.02512 (18)	0.0517 (6)
C16	0.7491 (3)	0.31478 (13)	−0.0077 (3)	0.0625 (8)
C17	0.7804 (3)	0.32943 (15)	−0.1054 (3)	0.0652 (9)
C18	0.8013 (3)	0.28801 (15)	−0.1738 (3)	0.0588 (8)
C19	0.7913 (2)	0.23223 (12)	−0.1432 (2)	0.0461 (6)
C20	0.7619 (2)	0.22130 (11)	−0.04182 (19)	0.0403 (6)
C21	0.7576 (2)	0.16390 (11)	−0.00682 (19)	0.0392 (6)
N22	0.7348 (2)	0.15386 (9)	0.09291 (17)	0.0492 (6)
C23	0.7375 (3)	0.10111 (13)	0.1236 (3)	0.0568 (8)
C24	0.7600 (3)	0.05586 (13)	0.0609 (3)	0.0587 (8)
C25	0.7791 (3)	0.06537 (13)	−0.0396 (3)	0.0571 (8)
C26	0.7790 (2)	0.12058 (12)	−0.0764 (2)	0.0457 (6)
C27	0.8038 (3)	0.13373 (16)	−0.1800 (2)	0.0596 (8)
C28	0.8114 (3)	0.18678 (16)	−0.2117 (2)	0.0604 (8)
N29	0.4351 (2)	0.16575 (10)	0.09219 (18)	0.0518 (6)
C30	0.4273 (3)	0.11227 (13)	0.1174 (3)	0.0599 (8)
C31	0.4212 (3)	0.06853 (14)	0.0472 (3)	0.0641 (9)
C32	0.4242 (3)	0.08067 (13)	−0.0547 (3)	0.0604 (8)
C33	0.4268 (2)	0.13634 (12)	−0.0870 (2)	0.0481 (6)
C34	0.4324 (2)	0.17825 (11)	−0.0104 (2)	0.0420 (6)
C35	0.4326 (2)	0.23641 (11)	−0.0405 (2)	0.0440 (6)
N36	0.4405 (2)	0.27609 (10)	0.0341 (2)	0.0558 (6)
C37	0.4345 (3)	0.32924 (14)	0.0038 (3)	0.0670 (9)
C38	0.4229 (3)	0.34606 (16)	−0.0987 (3)	0.0718 (10)
C39	0.4178 (3)	0.30656 (16)	−0.1739 (3)	0.0669 (9)
C40	0.4225 (3)	0.24953 (13)	−0.1472 (2)	0.0515 (7)
C41	0.4163 (3)	0.20588 (17)	−0.2215 (3)	0.0645 (9)
C42	0.4211 (3)	0.15191 (16)	−0.1934 (3)	0.0626 (8)
C43	0.1561 (2)	0.02471 (10)	0.29068 (19)	0.0372 (5)
N44	0.27230 (18)	0.01851 (9)	0.27136 (15)	0.0375 (5)
C45	0.3548 (2)	0.01003 (10)	0.34987 (18)	0.0352 (5)
N46	0.32209 (19)	0.01210 (9)	0.45126 (16)	0.0375 (5)
C47	0.2059 (2)	0.01347 (10)	0.47500 (18)	0.0378 (5)
N48	0.1252 (2)	0.01806 (10)	0.39225 (16)	0.0429 (5)
H2	0.617 (3)	0.3690 (15)	0.188 (3)	0.076 (10)*
H3	0.610 (3)	0.4425 (14)	0.303 (2)	0.062 (9)*
H4	0.607 (3)	0.4252 (13)	0.485 (2)	0.061 (9)*
H9	0.594 (3)	0.1188 (14)	0.324 (3)	0.066 (9)*
H10	0.592 (3)	0.0902 (14)	0.499 (3)	0.067 (9)*
H11	0.595 (3)	0.1600 (13)	0.631 (3)	0.065 (9)*
H13	0.605 (3)	0.2602 (14)	0.673 (3)	0.074 (10)*
H14	0.610 (3)	0.3550 (14)	0.619 (3)	0.064 (9)*
H16	0.729 (3)	0.3449 (15)	0.041 (3)	0.075 (10)*
H17	0.791 (4)	0.3682 (17)	−0.127 (3)	0.093 (12)*
H18	0.819 (3)	0.2971 (15)	−0.242 (3)	0.082 (11)*
H23	0.726 (3)	0.0961 (14)	0.195 (3)	0.069 (10)*
H24	0.766 (3)	0.0192 (15)	0.093 (3)	0.067 (10)*
H25	0.797 (3)	0.0347 (17)	−0.085 (3)	0.087 (12)*
H27	0.812 (3)	0.1029 (16)	−0.223 (3)	0.082 (11)*
H28	0.826 (3)	0.1957 (16)	−0.279 (3)	0.084 (11)*
H30	0.427 (3)	0.1037 (15)	0.193 (3)	0.078 (11)*
H31	0.417 (3)	0.0312 (16)	0.074 (3)	0.073 (10)*
H32	0.420 (3)	0.0524 (14)	−0.105 (3)	0.067 (10)*
H37	0.437 (3)	0.3575 (16)	0.065 (3)	0.082 (11)*
H38	0.415 (3)	0.3860 (16)	−0.114 (3)	0.083 (11)*
H39	0.409 (3)	0.3154 (15)	−0.250 (3)	0.075 (10)*
H41	0.412 (4)	0.2170 (17)	−0.291 (3)	0.095 (13)*
H42	0.416 (3)	0.1208 (14)	−0.246 (3)	0.066 (9)*
H46	0.376 (3)	0.0091 (12)	0.502 (2)	0.046 (8)*
H48	0.045 (3)	0.0165 (13)	0.403 (2)	0.059 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0489 (4)	0.0574 (4)	0.0407 (4)	0.0005 (3)	−0.0012 (3)	0.0101 (3)
S2	0.0397 (4)	0.0616 (4)	0.0372 (3)	0.0030 (3)	0.0113 (3)	−0.0022 (3)
S3	0.0445 (4)	0.0992 (6)	0.0316 (3)	0.0014 (4)	0.0111 (3)	−0.0006 (4)
Na	0.0762 (8)	0.0392 (6)	0.0360 (5)	0.0006 (5)	0.0146 (5)	−0.0035 (4)
N1	0.0578 (14)	0.0370 (11)	0.0359 (11)	0.0002 (10)	0.0117 (10)	−0.0012 (9)
C2	0.071 (2)	0.0421 (15)	0.0459 (16)	0.0018 (13)	0.0173 (14)	0.0040 (12)
C3	0.0618 (19)	0.0355 (14)	0.0581 (18)	0.0010 (13)	0.0111 (14)	0.0008 (13)
C4	0.0560 (17)	0.0389 (14)	0.0536 (17)	−0.0032 (12)	0.0116 (13)	−0.0116 (13)
C5	0.0408 (14)	0.0411 (14)	0.0424 (14)	−0.0031 (11)	0.0082 (11)	−0.0073 (11)
C6	0.0362 (13)	0.0371 (13)	0.0347 (12)	−0.0001 (10)	0.0067 (10)	−0.0029 (10)
C7	0.0370 (13)	0.0374 (13)	0.0343 (12)	0.0005 (10)	0.0065 (10)	−0.0025 (10)
N8	0.0554 (14)	0.0361 (11)	0.0413 (12)	0.0013 (10)	0.0105 (10)	−0.0032 (9)
C9	0.072 (2)	0.0379 (14)	0.0483 (16)	0.0001 (13)	0.0106 (14)	−0.0023 (12)
C10	0.074 (2)	0.0412 (16)	0.0553 (18)	0.0020 (14)	0.0103 (15)	0.0085 (13)
C11	0.069 (2)	0.0499 (16)	0.0425 (16)	−0.0008 (14)	0.0038 (14)	0.0101 (13)
C12	0.0471 (15)	0.0466 (14)	0.0345 (13)	0.0003 (11)	0.0037 (11)	0.0003 (11)
C13	0.072 (2)	0.0583 (18)	0.0323 (14)	−0.0044 (15)	0.0047 (13)	−0.0032 (13)
C14	0.070 (2)	0.0537 (17)	0.0393 (15)	−0.0063 (14)	0.0073 (13)	−0.0141 (13)
N15	0.0684 (16)	0.0431 (13)	0.0454 (13)	0.0016 (11)	0.0159 (11)	−0.0048 (10)
C16	0.082 (2)	0.0459 (17)	0.0618 (19)	0.0037 (15)	0.0225 (17)	0.0002 (15)
C17	0.074 (2)	0.0553 (19)	0.068 (2)	0.0000 (16)	0.0152 (17)	0.0143 (16)
C18	0.0573 (19)	0.071 (2)	0.0488 (17)	−0.0022 (15)	0.0107 (14)	0.0136 (16)
C19	0.0386 (14)	0.0617 (17)	0.0384 (14)	0.0022 (12)	0.0051 (11)	−0.0011 (12)
C20	0.0368 (13)	0.0479 (14)	0.0364 (13)	0.0020 (11)	0.0032 (10)	−0.0029 (11)
C21	0.0334 (13)	0.0450 (14)	0.0393 (13)	0.0028 (10)	0.0039 (10)	−0.0065 (11)
N22	0.0643 (15)	0.0426 (12)	0.0416 (12)	0.0035 (11)	0.0101 (11)	−0.0025 (10)
C23	0.068 (2)	0.0492 (17)	0.0538 (18)	0.0038 (14)	0.0067 (15)	0.0042 (14)
C24	0.0596 (19)	0.0401 (16)	0.076 (2)	0.0063 (13)	0.0025 (16)	−0.0022 (15)
C25	0.0524 (18)	0.0480 (17)	0.071 (2)	0.0061 (13)	0.0067 (15)	−0.0166 (15)
C26	0.0368 (14)	0.0516 (16)	0.0489 (15)	0.0021 (11)	0.0050 (12)	−0.0136 (12)
C27	0.062 (2)	0.072 (2)	0.0460 (16)	0.0059 (16)	0.0126 (14)	−0.0209 (16)
C28	0.061 (2)	0.082 (2)	0.0399 (16)	0.0054 (16)	0.0145 (14)	−0.0063 (16)
N29	0.0632 (16)	0.0483 (13)	0.0441 (13)	−0.0033 (11)	0.0053 (11)	0.0037 (10)
C30	0.067 (2)	0.0528 (18)	0.059 (2)	−0.0025 (15)	0.0038 (16)	0.0096 (15)
C31	0.064 (2)	0.0465 (18)	0.081 (2)	−0.0014 (15)	0.0007 (17)	0.0051 (17)
C32	0.0539 (19)	0.0493 (17)	0.078 (2)	0.0026 (14)	0.0048 (16)	−0.0120 (17)
C33	0.0379 (14)	0.0564 (16)	0.0505 (16)	−0.0002 (12)	0.0064 (12)	−0.0072 (13)
C34	0.0347 (13)	0.0480 (15)	0.0438 (14)	−0.0008 (11)	0.0062 (11)	−0.0002 (12)
C35	0.0370 (14)	0.0509 (15)	0.0447 (14)	0.0017 (11)	0.0061 (11)	0.0032 (12)
N36	0.0670 (17)	0.0459 (13)	0.0552 (15)	0.0007 (11)	0.0081 (12)	0.0014 (11)
C37	0.075 (2)	0.0484 (18)	0.077 (2)	0.0031 (16)	0.0063 (18)	0.0050 (17)
C38	0.068 (2)	0.055 (2)	0.093 (3)	0.0032 (17)	0.0048 (19)	0.025 (2)
C39	0.064 (2)	0.075 (2)	0.061 (2)	0.0039 (17)	0.0028 (16)	0.0233 (18)
C40	0.0428 (15)	0.0637 (18)	0.0479 (16)	−0.0022 (13)	0.0031 (12)	0.0098 (14)
C41	0.066 (2)	0.088 (3)	0.0397 (16)	−0.0064 (18)	0.0050 (14)	0.0017 (16)
C42	0.062 (2)	0.078 (2)	0.0493 (17)	−0.0057 (17)	0.0104 (15)	−0.0132 (17)
C43	0.0445 (14)	0.0316 (12)	0.0356 (12)	−0.0045 (10)	0.0049 (10)	0.0031 (10)
N44	0.0384 (12)	0.0434 (11)	0.0312 (10)	−0.0031 (9)	0.0065 (9)	0.0010 (9)
C45	0.0413 (13)	0.0325 (12)	0.0330 (12)	−0.0033 (10)	0.0100 (10)	−0.0008 (9)
N46	0.0353 (12)	0.0464 (12)	0.0313 (11)	0.0007 (9)	0.0049 (9)	−0.0006 (9)
C47	0.0393 (14)	0.0406 (13)	0.0342 (13)	0.0024 (10)	0.0075 (10)	0.0003 (10)
N48	0.0357 (12)	0.0596 (14)	0.0340 (11)	−0.0002 (10)	0.0067 (9)	0.0057 (10)

Geometric parameters (Å, º)

S1—C43	1.658 (3)	C21—C26	1.404 (3)
S2—C45	1.682 (2)	N22—C23	1.320 (4)
S3—C47	1.663 (2)	C23—C24	1.386 (4)
Na—N1	2.430 (2)	C23—H23	0.96 (3)
Na—N8	2.464 (2)	C24—C25	1.353 (5)
Na—N15	2.558 (3)	C24—H24	0.97 (3)
Na—N22	2.548 (2)	C25—C26	1.401 (4)
Na—N29	2.582 (3)	C25—H25	0.97 (4)
Na—N36	2.656 (3)	C26—C27	1.426 (4)
N1—C2	1.324 (3)	C27—C28	1.336 (5)
N1—C6	1.357 (3)	C27—H27	0.93 (4)
C2—C3	1.390 (4)	C28—H28	0.93 (4)
C2—H2	0.96 (4)	N29—C30	1.322 (4)
C3—C4	1.351 (4)	N29—C34	1.359 (3)
C3—H3	0.93 (3)	C30—C31	1.382 (5)
C4—C5	1.400 (4)	C30—H30	1.00 (4)
C4—H4	1.00 (3)	C31—C32	1.354 (5)
C5—C6	1.402 (3)	C31—H31	0.96 (4)
C5—C14	1.428 (4)	C32—C33	1.394 (4)
C6—C7	1.445 (3)	C32—H32	0.93 (3)
C7—N8	1.353 (3)	C33—C34	1.406 (4)
C7—C12	1.406 (3)	C33—C42	1.423 (4)
N8—C9	1.325 (3)	C34—C35	1.442 (4)
C9—C10	1.387 (4)	C35—N36	1.350 (4)
C9—H9	0.97 (3)	C35—C40	1.412 (4)
C10—C11	1.358 (4)	N36—C37	1.328 (4)
C10—H10	0.97 (3)	C37—C38	1.382 (5)
C11—C12	1.402 (4)	C37—H37	1.03 (4)
C11—H11	1.00 (3)	C38—C39	1.352 (5)
C12—C13	1.425 (4)	C38—H38	0.98 (4)
C13—C14	1.336 (4)	C39—C40	1.404 (5)
C13—H13	0.97 (4)	C39—H39	1.00 (4)
C14—H14	0.95 (3)	C40—C41	1.415 (5)
N15—C16	1.321 (4)	C41—C42	1.338 (5)
N15—C20	1.352 (3)	C41—H41	0.94 (4)
C16—C17	1.383 (5)	C42—H42	1.00 (3)
C16—H16	1.00 (4)	C43—N44	1.345 (3)
C17—C18	1.360 (5)	C43—N48	1.394 (3)
C17—H17	0.98 (4)	N44—C45	1.329 (3)
C18—C19	1.396 (4)	C45—N46	1.390 (3)
C18—H18	0.94 (4)	N46—C47	1.353 (3)
C19—C20	1.402 (4)	N46—H46	0.85 (3)
C19—C28	1.430 (4)	C47—N48	1.346 (3)
C20—C21	1.445 (4)	N48—H48	0.91 (3)
C21—N22	1.356 (3)
N1—Na—N8	68.13 (7)	C23—N22—Na	124.8 (2)
N1—Na—N22	143.27 (9)	C21—N22—Na	112.46 (16)
N8—Na—N22	100.51 (8)	N22—C23—C24	124.6 (3)
N1—Na—N15	103.81 (8)	N22—C23—H23	114 (2)
N8—Na—N15	145.34 (10)	C24—C23—H23	121 (2)
N22—Na—N15	65.03 (8)	C25—C24—C23	118.8 (3)
N1—Na—N29	133.04 (9)	C25—C24—H24	123 (2)
N8—Na—N29	96.25 (8)	C23—C24—H24	118 (2)
N22—Na—N29	81.43 (8)	C24—C25—C26	119.2 (3)
N15—Na—N29	111.33 (8)	C24—C25—H25	121 (2)
N1—Na—N36	94.83 (8)	C26—C25—H25	120 (2)
N8—Na—N36	133.03 (9)	C25—C26—C21	118.1 (3)
N22—Na—N36	115.73 (8)	C25—C26—C27	122.1 (3)
N15—Na—N36	79.90 (8)	C21—C26—C27	119.8 (3)
N29—Na—N36	63.08 (8)	C28—C27—C26	121.3 (3)
C2—N1—C6	117.0 (2)	C28—C27—H27	123 (2)
C2—N1—Na	124.83 (18)	C26—C27—H27	115 (2)
C6—N1—Na	118.08 (16)	C27—C28—C19	120.8 (3)
N1—C2—C3	124.4 (3)	C27—C28—H28	122 (2)
N1—C2—H2	115 (2)	C19—C28—H28	117 (2)
C3—C2—H2	120 (2)	C30—N29—C34	117.2 (3)
C4—C3—C2	118.8 (3)	C30—N29—Na	123.1 (2)
C4—C3—H3	123 (2)	C34—N29—Na	101.03 (17)
C2—C3—H3	118 (2)	N29—C30—C31	124.6 (3)
C3—C4—C5	119.3 (3)	N29—C30—H30	116 (2)
C3—C4—H4	122.7 (18)	C31—C30—H30	119 (2)
C5—C4—H4	118.0 (18)	C32—C31—C30	118.4 (3)
C4—C5—C6	118.3 (2)	C32—C31—H31	124 (2)
C4—C5—C14	122.3 (2)	C30—C31—H31	118 (2)
C6—C5—C14	119.5 (2)	C31—C32—C33	119.9 (3)
N1—C6—C5	122.2 (2)	C31—C32—H32	121 (2)
N1—C6—C7	118.1 (2)	C33—C32—H32	119 (2)
C5—C6—C7	119.7 (2)	C32—C33—C34	117.9 (3)
N8—C7—C12	122.3 (2)	C32—C33—C42	122.6 (3)
N8—C7—C6	119.0 (2)	C34—C33—C42	119.5 (3)
C12—C7—C6	118.6 (2)	N29—C34—C33	121.9 (3)
C9—N8—C7	117.2 (2)	N29—C34—C35	118.4 (2)
C9—N8—Na	126.16 (18)	C33—C34—C35	119.7 (2)
C7—N8—Na	116.57 (16)	N36—C35—C40	122.7 (3)
N8—C9—C10	124.4 (3)	N36—C35—C34	118.9 (2)
N8—C9—H9	114.1 (19)	C40—C35—C34	118.4 (3)
C10—C9—H9	121.4 (19)	C37—N36—C35	117.4 (3)
C11—C10—C9	118.6 (3)	C37—N36—Na	126.8 (2)
C11—C10—H10	122 (2)	C35—N36—Na	100.13 (17)
C9—C10—H10	120 (2)	N36—C37—C38	124.0 (4)
C10—C11—C12	119.5 (3)	N36—C37—H37	114 (2)
C10—C11—H11	120.8 (19)	C38—C37—H37	122 (2)
C12—C11—H11	119.7 (19)	C39—C38—C37	118.9 (3)
C11—C12—C7	117.9 (2)	C39—C38—H38	123 (2)
C11—C12—C13	122.2 (3)	C37—C38—H38	118 (2)
C7—C12—C13	119.9 (2)	C38—C39—C40	120.0 (3)
C14—C13—C12	121.2 (3)	C38—C39—H39	124 (2)
C14—C13—H13	122 (2)	C40—C39—H39	116 (2)
C12—C13—H13	117 (2)	C39—C40—C35	117.0 (3)
C13—C14—C5	121.1 (3)	C39—C40—C41	123.2 (3)
C13—C14—H14	123.3 (19)	C35—C40—C41	119.8 (3)
C5—C14—H14	116 (2)	C42—C41—C40	121.7 (3)
C16—N15—C20	117.2 (3)	C42—C41—H41	122 (3)
C16—N15—Na	125.6 (2)	C40—C41—H41	116 (3)
C20—N15—Na	112.75 (17)	C41—C42—C33	120.8 (3)
N15—C16—C17	124.5 (3)	C41—C42—H42	122.0 (19)
N15—C16—H16	116 (2)	C33—C42—H42	117.2 (19)
C17—C16—H16	119 (2)	N44—C43—N48	118.4 (2)
C18—C17—C16	118.7 (3)	N44—C43—S1	124.02 (18)
C18—C17—H17	118 (2)	N48—C43—S1	117.55 (19)
C16—C17—H17	123 (2)	C45—N44—C43	119.3 (2)
C17—C18—C19	119.2 (3)	N44—C45—N46	120.0 (2)
C17—C18—H18	120 (2)	N44—C45—S2	122.74 (18)
C19—C18—H18	121 (2)	N46—C45—S2	117.28 (19)
C18—C19—C20	118.2 (3)	C47—N46—C45	122.8 (2)
C18—C19—C28	121.9 (3)	C47—N46—H46	117 (2)
C20—C19—C28	119.9 (3)	C45—N46—H46	120 (2)
N15—C20—C19	122.3 (2)	N48—C47—N46	114.2 (2)
N15—C20—C21	118.7 (2)	N48—C47—S3	123.39 (19)
C19—C20—C21	119.1 (2)	N46—C47—S3	122.39 (19)
N22—C21—C26	122.3 (2)	C47—N48—C43	124.1 (2)
N22—C21—C20	118.6 (2)	C47—N48—H48	118 (2)
C26—C21—C20	119.1 (2)	C43—N48—H48	118 (2)
C23—N22—C21	117.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N46—H46···S2^i	0.85 (3)	2.46 (3)	3.298 (2)	170 (3)
N48—H48···S3^ii	0.91 (3)	2.44 (3)	3.336 (2)	165 (3)

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