(Isopropyl xanthato-κ2S,S′)bis­(1,10-phenanthroline-κ2N,N′)sodium(I)

Li, F.

doi:10.1107/S1600536807061910

metal-organic compounds

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Volume 64| Part 1| January 2008| Page m27

https://doi.org/10.1107/S1600536807061910

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(Isopropyl xanthato-κ²S,S′)bis(1,10-phenanthroline-κ²N,N′)sodium(I)

Feng Li ^a ^*

^aDepartment of Chemistry, Luliang Higher College, Shanxi 033000, People's Republic of China
^*Correspondence e-mail: lifeng1982@163.com

(Received 19 November 2007; accepted 21 November 2007; online 6 December 2007)

The title compound, [Na(C₄H₇OS₂)(C₁₂H₈N₂)₂], is monomeric, with the Na atom chelated by the S atoms of an i-propylxanthate ligand and the N atoms of two 1,10-phenanthroline (phen) ligands. The Na atom is six-coordinate in a distorted trigonal antiprism. A number of π–π stacking interactions involving the phen rings help to consolidate the crystal packing (centroid–centroid distances lie in the range 3.338–3.443 Å).

Related literature

For the structures of related complexes, see: Arnold (1995 ). For a comparison of π–π stacking interactions, see: Janiak (2000 ).

Experimental

Crystal data

[Na(C₄H₇OS₂)(C₁₂H₈N₂)₂]
M_r = 518.61
Monoclinic, P 2₁ /c
a = 16.529 (4) Å
b = 12.153 (3) Å
c = 13.002 (3) Å
β = 102.557 (4)°
V = 2549.5 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 (2) K
0.23 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.944, T_max = 0.960
13248 measured reflections
4495 independent reflections
2440 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.127
S = 1.00
4495 reflections
327 parameters
102 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Na1—N3	2.470 (3)
Na1—N4	2.492 (3)
Na1—N2	2.501 (3)
Na1—N1	2.523 (3)
Na1—S1	2.9188 (15)
Na1—S2	3.1265 (16)

N3—Na1—N4	66.79 (9)
N3—Na1—N2	94.11 (10)
N4—Na1—N2	88.26 (9)
N3—Na1—N1	92.54 (9)
N4—Na1—N1	146.48 (10)
N2—Na1—N1	66.31 (9)
N3—Na1—S1	107.62 (7)
N4—Na1—S1	124.66 (7)
N2—Na1—S1	145.46 (8)
N1—Na1—S1	85.78 (7)
N3—Na1—S2	134.91 (8)
N4—Na1—S2	85.99 (7)
N2—Na1—S2	121.38 (8)
N1—Na1—S2	125.37 (7)
S1—Na1—S2	58.81 (4)

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807061910/sq2005sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061910/sq2005Isup2.hkl

checkCIF report

Comment top

So far only a handful of sodium chalcogenolates have been investigated in the solid state (Arnold et al., 1995). As a continuation of our interest in sulfur-containing ligands, in this paper we report the synthesis and structural characterization of the title compound, (I).

The title compound, (I), is monomeric, with the Na atom chelated by the S atoms of an i-propylxanthate ligand and the nitrogen atoms of two 1,10-phenanthroline ligands (Fig. 1). The metal is six-coordinate in a coordination polyhedron that can be described as a distorted trigonal antiprism. The plane defined by S1, N1 and N3 is essentially parallel to that defined by S2, N2 and N4 (the two planes are inclined by 7.1°) and Na is displaced by 1.35 and 1.24 Å away from these planes, respectively.

A number of π-π stacking interactions involving the phen rings help to consolidate the crystal packing (Fig. 2). The Cg···Cg (Cg = ring centroid) distances lie in the range 3.338–3.443 Å, which is normal for such interactions (Janiak, 2000) and lead to the formation of an infinite one-dimensional chain network structure along the a axis.

Related literature top

For the structures of related complexes, see: Arnold (1995). For a comparison of π-π stacking interactions, see: Janiak (2000).

Experimental top

To an acetonitrile solution of NaI (1.0 mmol) was added another acetonitrile solution of sodium i-propylxanthate (1.0 mmol) and phenanthroline (2.0 mmol). The resulting solution was stirred for 3.0 h at room temperature and a yellow-red solid was obtained by filtration. The product was recrystallized in acetone to give yellow-red crystals. Yield 82%. m.p.:436 K. Anal. Calcd. (%) for C₂₈H₂₃NaON₄S₂ (Mr = 518.61): C, 64.84; H, 4.47; N, 10.80. Found (%): C, 64.52; H, 4.23; N, 10.67.

Structure description top

For the structures of related complexes, see: Arnold (1995). For a comparison of π-π stacking interactions, see: Janiak (2000).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Crystal packing of (I) showing π-π stacking interactions (dashed lines) along the a axis.

(Isopropyl xanthato-κ²S,S')bis(1,10-phenanthroline-κ²N,N')sodium(I) top

Crystal data top

[Na(C₄H₇OS₂)(C₁₂H₈N₂)₂]	F(000) = 1080
M_r = 518.61	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.529 (4) Å	Cell parameters from 2319 reflections
b = 12.153 (3) Å	θ = 2.3–21.4°
c = 13.002 (3) Å	µ = 0.26 mm⁻¹
β = 102.557 (4)°	T = 298 K
V = 2549.5 (11) Å³	Block, yellow
Z = 4	0.23 × 0.22 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4495 independent reflections
Radiation source: fine-focus sealed tube	2440 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
phi and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→19
T_min = 0.944, T_max = 0.960	k = −13→14
13248 measured reflections	l = −15→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0469P)² + 0.6823P] where P = (F_o² + 2F_c²)/3
4495 reflections	(Δ/σ)_max < 0.001
327 parameters	Δρ_max = 0.23 e Å⁻³
102 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Na(C₄H₇OS₂)(C₁₂H₈N₂)₂]	V = 2549.5 (11) Å³
M_r = 518.61	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.529 (4) Å	µ = 0.26 mm⁻¹
b = 12.153 (3) Å	T = 298 K
c = 13.002 (3) Å	0.23 × 0.22 × 0.16 mm
β = 102.557 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4495 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2440 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.960	R_int = 0.043
13248 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	102 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
4495 reflections	Δρ_min = −0.22 e Å⁻³
327 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Na1	0.24442 (7)	0.42828 (10)	0.49678 (9)	0.0561 (4)
S1	0.23574 (6)	0.23226 (7)	0.36513 (6)	0.0594 (3)
S2	0.26704 (6)	0.19302 (7)	0.59616 (6)	0.0652 (3)
N1	0.11912 (15)	0.4938 (2)	0.3635 (2)	0.0542 (7)
N2	0.16281 (16)	0.5731 (2)	0.5659 (2)	0.0571 (7)
N3	0.33660 (16)	0.5616 (2)	0.4359 (2)	0.0543 (7)
N4	0.36660 (15)	0.4814 (2)	0.6368 (2)	0.0522 (7)
O1	0.25533 (14)	0.04248 (16)	0.44589 (16)	0.0656 (7)
C1	0.0964 (2)	0.4556 (3)	0.2670 (3)	0.0641 (10)
H1	0.1330	0.4096	0.2423	0.077*
C2	0.0208 (2)	0.4798 (3)	0.1992 (3)	0.0664 (10)
H2	0.0079	0.4511	0.1313	0.080*
C3	−0.0334 (2)	0.5456 (3)	0.2341 (3)	0.0631 (10)
H3	−0.0845	0.5617	0.1905	0.076*
C4	−0.01268 (19)	0.5897 (2)	0.3358 (3)	0.0534 (8)
C5	0.06533 (18)	0.5611 (2)	0.3984 (2)	0.0481 (8)
C6	0.08858 (19)	0.6039 (2)	0.5051 (2)	0.0483 (8)
C7	0.0332 (2)	0.6737 (2)	0.5417 (3)	0.0569 (9)
C8	0.0581 (3)	0.7141 (3)	0.6447 (3)	0.0719 (11)
H8	0.0236	0.7611	0.6720	0.086*
C9	0.1327 (3)	0.6846 (3)	0.7041 (3)	0.0757 (11)
H9	0.1504	0.7116	0.7722	0.091*
C10	0.1822 (2)	0.6135 (3)	0.6620 (3)	0.0680 (10)
H10	0.2327	0.5928	0.7045	0.082*
C11	−0.0666 (2)	0.6609 (3)	0.3771 (3)	0.0670 (10)
H11	−0.1178	0.6797	0.3352	0.080*
C12	−0.0449 (2)	0.7008 (3)	0.4744 (3)	0.0708 (11)
H12	−0.0811	0.7472	0.4992	0.085*
C13	0.3242 (2)	0.6017 (3)	0.3396 (3)	0.0688 (10)
H13	0.2752	0.5827	0.2930	0.083*
C14	0.3786 (3)	0.6699 (3)	0.3027 (3)	0.0802 (12)
H14	0.3661	0.6958	0.2338	0.096*
C15	0.4505 (3)	0.6979 (3)	0.3695 (3)	0.0717 (11)
H15	0.4884	0.7428	0.3464	0.086*
C16	0.4675 (2)	0.6591 (2)	0.4731 (3)	0.0541 (8)
C17	0.40810 (18)	0.5912 (2)	0.5034 (2)	0.0455 (8)
C18	0.42288 (18)	0.5493 (2)	0.6098 (2)	0.0440 (7)
C19	0.49649 (19)	0.5806 (2)	0.6811 (3)	0.0514 (8)
C20	0.5093 (2)	0.5388 (3)	0.7836 (3)	0.0644 (10)
H20	0.5570	0.5575	0.8330	0.077*
C21	0.4525 (2)	0.4713 (3)	0.8106 (3)	0.0667 (10)
H21	0.4601	0.4436	0.8787	0.080*
C22	0.3821 (2)	0.4440 (3)	0.7342 (3)	0.0647 (9)
H22	0.3438	0.3965	0.7532	0.078*
C23	0.5415 (2)	0.6870 (3)	0.5485 (3)	0.0651 (10)
H23	0.5808	0.7320	0.5282	0.078*
C24	0.5552 (2)	0.6498 (3)	0.6469 (3)	0.0641 (10)
H24	0.6038	0.6693	0.6942	0.077*
C25	0.25295 (16)	0.1505 (2)	0.4714 (2)	0.0446 (7)
C26	0.2626 (2)	−0.0430 (3)	0.5236 (2)	0.0622 (10)
H26	0.2900	−0.0141	0.5928	0.075*
C27	0.1785 (3)	−0.0821 (4)	0.5268 (3)	0.1047 (14)
H27A	0.1458	−0.0214	0.5420	0.157*
H27B	0.1822	−0.1370	0.5808	0.157*
H27C	0.1529	−0.1134	0.4599	0.157*
C28	0.3157 (3)	−0.1305 (3)	0.4899 (3)	0.1062 (15)
H28A	0.2909	−0.1542	0.4196	0.159*
H28B	0.3202	−0.1920	0.5371	0.159*
H28C	0.3699	−0.1012	0.4913	0.159*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0451 (7)	0.0543 (7)	0.0660 (8)	−0.0008 (6)	0.0060 (6)	−0.0073 (6)
S1	0.0697 (6)	0.0538 (5)	0.0522 (5)	−0.0038 (4)	0.0078 (4)	0.0015 (4)
S2	0.0852 (7)	0.0600 (5)	0.0466 (5)	0.0113 (5)	0.0062 (4)	−0.0070 (4)
N1	0.0462 (17)	0.0547 (16)	0.0613 (18)	0.0053 (14)	0.0110 (14)	−0.0046 (14)
N2	0.0554 (18)	0.0576 (16)	0.0582 (18)	0.0005 (14)	0.0122 (14)	−0.0064 (14)
N3	0.0547 (18)	0.0561 (16)	0.0509 (17)	0.0019 (13)	0.0088 (14)	0.0003 (14)
N4	0.0458 (16)	0.0530 (15)	0.0581 (17)	−0.0046 (13)	0.0123 (13)	0.0032 (14)
O1	0.1042 (19)	0.0457 (13)	0.0483 (13)	0.0012 (12)	0.0195 (12)	−0.0033 (11)
C1	0.058 (2)	0.067 (2)	0.066 (2)	0.0055 (18)	0.0102 (19)	−0.0034 (19)
C2	0.067 (3)	0.067 (2)	0.061 (2)	−0.002 (2)	0.005 (2)	0.0041 (19)
C3	0.057 (2)	0.060 (2)	0.068 (2)	0.0004 (19)	0.0049 (19)	0.0182 (19)
C4	0.047 (2)	0.0450 (18)	0.069 (2)	0.0067 (16)	0.0158 (17)	0.0201 (17)
C5	0.0429 (19)	0.0396 (17)	0.063 (2)	−0.0008 (15)	0.0148 (16)	0.0059 (16)
C6	0.050 (2)	0.0354 (16)	0.062 (2)	−0.0004 (15)	0.0191 (17)	0.0068 (15)
C7	0.068 (2)	0.0387 (18)	0.071 (2)	0.0048 (17)	0.030 (2)	0.0101 (17)
C8	0.101 (3)	0.047 (2)	0.081 (3)	0.012 (2)	0.048 (2)	0.005 (2)
C9	0.102 (3)	0.064 (2)	0.067 (2)	−0.001 (2)	0.031 (2)	−0.009 (2)
C10	0.069 (3)	0.073 (2)	0.063 (2)	0.003 (2)	0.017 (2)	−0.007 (2)
C11	0.057 (2)	0.058 (2)	0.088 (3)	0.0176 (18)	0.021 (2)	0.027 (2)
C12	0.075 (3)	0.052 (2)	0.094 (3)	0.0234 (19)	0.037 (2)	0.018 (2)
C13	0.073 (3)	0.072 (2)	0.058 (2)	0.009 (2)	0.009 (2)	−0.001 (2)
C14	0.115 (4)	0.069 (3)	0.059 (2)	0.019 (3)	0.027 (3)	0.014 (2)
C15	0.096 (3)	0.048 (2)	0.084 (3)	0.004 (2)	0.049 (2)	0.005 (2)
C16	0.059 (2)	0.0376 (17)	0.072 (2)	0.0038 (16)	0.0283 (19)	−0.0034 (17)
C17	0.0429 (19)	0.0378 (16)	0.058 (2)	0.0023 (14)	0.0158 (16)	−0.0065 (15)
C18	0.0393 (18)	0.0377 (16)	0.056 (2)	0.0007 (14)	0.0126 (15)	−0.0033 (15)
C19	0.045 (2)	0.0425 (17)	0.065 (2)	0.0022 (15)	0.0076 (17)	−0.0132 (16)
C20	0.063 (2)	0.060 (2)	0.064 (2)	0.0070 (19)	0.0011 (19)	−0.0125 (19)
C21	0.080 (3)	0.068 (2)	0.050 (2)	0.008 (2)	0.011 (2)	0.0039 (18)
C22	0.069 (3)	0.060 (2)	0.068 (2)	−0.0030 (19)	0.020 (2)	0.0069 (19)
C23	0.058 (2)	0.0467 (19)	0.097 (3)	−0.0148 (17)	0.031 (2)	−0.011 (2)
C24	0.047 (2)	0.058 (2)	0.087 (3)	−0.0102 (18)	0.0121 (19)	−0.019 (2)
C25	0.0343 (17)	0.0451 (17)	0.0536 (18)	0.0008 (13)	0.0076 (14)	−0.0052 (15)
C26	0.083 (3)	0.050 (2)	0.051 (2)	0.0037 (18)	0.0111 (19)	0.0061 (16)
C27	0.110 (4)	0.111 (3)	0.095 (3)	−0.022 (3)	0.027 (3)	0.028 (3)
C28	0.138 (4)	0.079 (3)	0.101 (3)	0.039 (3)	0.023 (3)	0.001 (2)

Geometric parameters (Å, º) top

Na1—N3	2.470 (3)	C10—H10	0.9300
Na1—N4	2.492 (3)	C11—C12	1.329 (5)
Na1—N2	2.501 (3)	C11—H11	0.9300
Na1—N1	2.523 (3)	C12—H12	0.9300
Na1—S1	2.9188 (15)	C13—C14	1.383 (5)
Na1—S2	3.1265 (16)	C13—H13	0.9300
S1—C25	1.675 (3)	C14—C15	1.354 (5)
S2—C25	1.670 (3)	C14—H14	0.9300
N1—C1	1.314 (4)	C15—C16	1.397 (5)
N1—C5	1.357 (4)	C15—H15	0.9300
N2—C10	1.315 (4)	C16—C17	1.403 (4)
N2—C6	1.360 (4)	C16—C23	1.432 (4)
N3—C13	1.317 (4)	C17—C18	1.444 (4)
N3—C17	1.359 (3)	C18—C19	1.412 (4)
N4—C22	1.316 (4)	C19—C20	1.399 (4)
N4—C18	1.346 (4)	C19—C24	1.425 (4)
O1—C25	1.357 (3)	C20—C21	1.349 (4)
O1—C26	1.435 (3)	C20—H20	0.9300
C1—C2	1.395 (4)	C21—C22	1.396 (4)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.351 (4)	C22—H22	0.9300
C2—H2	0.9300	C23—C24	1.329 (4)
C3—C4	1.398 (4)	C23—H23	0.9300
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.411 (4)	C26—C27	1.478 (5)
C4—C11	1.429 (4)	C26—C28	1.504 (5)
C5—C6	1.452 (4)	C26—H26	0.9800
C6—C7	1.405 (4)	C27—H27A	0.9600
C7—C8	1.402 (5)	C27—H27B	0.9600
C7—C12	1.431 (4)	C27—H27C	0.9600
C8—C9	1.354 (5)	C28—H28A	0.9600
C8—H8	0.9300	C28—H28B	0.9600
C9—C10	1.382 (5)	C28—H28C	0.9600
C9—H9	0.9300

N3—Na1—N4	66.79 (9)	C4—C11—H11	119.4
N3—Na1—N2	94.11 (10)	C11—C12—C7	121.3 (3)
N4—Na1—N2	88.26 (9)	C11—C12—H12	119.3
N3—Na1—N1	92.54 (9)	C7—C12—H12	119.3
N4—Na1—N1	146.48 (10)	N3—C13—C14	125.0 (4)
N2—Na1—N1	66.31 (9)	N3—C13—H13	117.5
N3—Na1—S1	107.62 (7)	C14—C13—H13	117.5
N4—Na1—S1	124.66 (7)	C15—C14—C13	118.3 (4)
N2—Na1—S1	145.46 (8)	C15—C14—H14	120.9
N1—Na1—S1	85.78 (7)	C13—C14—H14	120.9
N3—Na1—S2	134.91 (8)	C14—C15—C16	119.9 (4)
N4—Na1—S2	85.99 (7)	C14—C15—H15	120.0
N2—Na1—S2	121.38 (8)	C16—C15—H15	120.0
N1—Na1—S2	125.37 (7)	C15—C16—C17	117.5 (3)
S1—Na1—S2	58.81 (4)	C15—C16—C23	123.0 (3)
C25—S1—Na1	91.28 (11)	C17—C16—C23	119.5 (3)
C25—S2—Na1	84.41 (11)	N3—C17—C16	122.5 (3)
C1—N1—C5	117.4 (3)	N3—C17—C18	117.9 (3)
C1—N1—Na1	124.5 (2)	C16—C17—C18	119.6 (3)
C5—N1—Na1	117.4 (2)	N4—C18—C19	122.7 (3)
C10—N2—C6	116.9 (3)	N4—C18—C17	118.9 (3)
C10—N2—Na1	124.4 (2)	C19—C18—C17	118.4 (3)
C6—N2—Na1	118.3 (2)	C20—C19—C18	117.2 (3)
C13—N3—C17	116.8 (3)	C20—C19—C24	122.6 (3)
C13—N3—Na1	124.6 (2)	C18—C19—C24	120.1 (3)
C17—N3—Na1	118.5 (2)	C21—C20—C19	120.0 (3)
C22—N4—C18	117.5 (3)	C21—C20—H20	120.0
C22—N4—Na1	124.8 (2)	C19—C20—H20	120.0
C18—N4—Na1	117.7 (2)	C20—C21—C22	118.5 (3)
C25—O1—C26	122.0 (2)	C20—C21—H21	120.7
N1—C1—C2	124.0 (3)	C22—C21—H21	120.7
N1—C1—H1	118.0	N4—C22—C21	124.1 (3)
C2—C1—H1	118.0	N4—C22—H22	117.9
C3—C2—C1	118.7 (3)	C21—C22—H22	117.9
C3—C2—H2	120.6	C24—C23—C16	121.3 (3)
C1—C2—H2	120.6	C24—C23—H23	119.3
C2—C3—C4	120.1 (3)	C16—C23—H23	119.3
C2—C3—H3	120.0	C23—C24—C19	121.1 (3)
C4—C3—H3	120.0	C23—C24—H24	119.5
C3—C4—C5	117.2 (3)	C19—C24—H24	119.5
C3—C4—C11	122.9 (3)	O1—C25—S2	122.1 (2)
C5—C4—C11	119.9 (3)	O1—C25—S1	112.4 (2)
N1—C5—C4	122.6 (3)	S2—C25—S1	125.50 (18)
N1—C5—C6	118.6 (3)	O1—C26—C27	108.5 (3)
C4—C5—C6	118.8 (3)	O1—C26—C28	105.7 (3)
N2—C6—C7	122.8 (3)	C27—C26—C28	113.1 (3)
N2—C6—C5	118.4 (3)	O1—C26—H26	109.8
C7—C6—C5	118.9 (3)	C27—C26—H26	109.8
C8—C7—C6	117.2 (3)	C28—C26—H26	109.8
C8—C7—C12	122.9 (3)	C26—C27—H27A	109.5
C6—C7—C12	119.9 (3)	C26—C27—H27B	109.5
C9—C8—C7	119.6 (4)	H27A—C27—H27B	109.5
C9—C8—H8	120.2	C26—C27—H27C	109.5
C7—C8—H8	120.2	H27A—C27—H27C	109.5
C8—C9—C10	118.9 (4)	H27B—C27—H27C	109.5
C8—C9—H9	120.5	C26—C28—H28A	109.5
C10—C9—H9	120.5	C26—C28—H28B	109.5
N2—C10—C9	124.5 (4)	H28A—C28—H28B	109.5
N2—C10—H10	117.7	C26—C28—H28C	109.5
C9—C10—H10	117.7	H28A—C28—H28C	109.5
C12—C11—C4	121.1 (3)	H28B—C28—H28C	109.5
C12—C11—H11	119.4

Experimental details

Crystal data
Chemical formula	[Na(C₄H₇OS₂)(C₁₂H₈N₂)₂]
M_r	518.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.529 (4), 12.153 (3), 13.002 (3)
β (°)	102.557 (4)
V (Å³)	2549.5 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.23 × 0.22 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.944, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	13248, 4495, 2440
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.127, 1.00
No. of reflections	4495
No. of parameters	327
No. of restraints	102
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.22

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected geometric parameters (Å, º) top

Na1—N3	2.470 (3)	Na1—N1	2.523 (3)
Na1—N4	2.492 (3)	Na1—S1	2.9188 (15)
Na1—N2	2.501 (3)	Na1—S2	3.1265 (16)

N3—Na1—N4	66.79 (9)	N2—Na1—S1	145.46 (8)
N3—Na1—N2	94.11 (10)	N1—Na1—S1	85.78 (7)
N4—Na1—N2	88.26 (9)	N3—Na1—S2	134.91 (8)
N3—Na1—N1	92.54 (9)	N4—Na1—S2	85.99 (7)
N4—Na1—N1	146.48 (10)	N2—Na1—S2	121.38 (8)
N2—Na1—N1	66.31 (9)	N1—Na1—S2	125.37 (7)
N3—Na1—S1	107.62 (7)	S1—Na1—S2	58.81 (4)
N4—Na1—S1	124.66 (7)

References

Arnold, J. (1995). Prog. Inorg. Chem. 43, 353–358. CrossRef CAS Web of Science Google Scholar
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885–3896. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997a). SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar