A triclinic modification of 5,5'-dinitro-2,2'-dithio-dipyridine.

The asymmetric unit of the title compound, C(10)H(6)N(4)O(4)S(2), contains two independent but similar mol-ecules. The structure is a triclinic polymorph of the monoclinic structure reported previously [Brito, Mundaca, Cárdenas, López-Rodríguez & Vargas (2007 ▶). Acta Cryst. E63, o3351-o3352]. The most obvious difference between the two polymorphs is the C-S-S-C torsion angle [-80.13 (16), -79.8 (2) and 0° for the two mol-ecules of the triclinic polymorph and the monoclinic polymorph, respectively]. The crystal structure of the title compound has two intra-molecular C-H⋯S inter-actions with average H⋯S distances of 2.69 Å, whereas this kind of inter-action is not evident in the monoclinic polymorph.

Related literature

For related literature, see: Allen et al. (1987 ▶); Bernstein et al. (1995 ▶); Brito et al. (2007 ▶); Glidewell et al. (2000 ▶); Shefter (1970 ▶).

Experimental

Crystal data

C10H6N4O4S2

M = 310.31

Triclinic,

a = 7.7832 (12) Å

b = 11.8515 (11) Å

c = 14.513 (2) Å

α = 82.353 (4)°

β = 82.095 (5)°

γ = 72.460 (9)°

V = 1258.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 298 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.937, T max = 0.948

11205 measured reflections

4931 independent reflections

4101 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.209

S = 1.16

4931 reflections

362 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062630/bt2643sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062630/bt2643Isup2.hkl

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

C10H6N4O4S2	Z = 4
Mr = 310.31	F000 = 632
Triclinic, P1	Dx = 1.638 Mg m−3
Hall symbol: -P 1	Melting point: 420 K
a = 7.7832 (12) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.8515 (11) Å	Cell parameters from 11236 reflections
c = 14.513 (2) Å	θ = 1.4–26.5º
α = 82.353 (4)º	µ = 0.44 mm−1
β = 82.095 (5)º	T = 298 (2) K
γ = 72.460 (9)º	Prismatic, light yellow
V = 1258.4 (3) Å3	0.20 × 0.10 × 0.10 mm

Nonius KappaCCD area-detector diffractometer	4101 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
Monochromator: graphite	θmax = 26.5º
φ scans, and ω scans with κ offsets	θmin = 1.4º
Absorption correction: multi-scan(SORTAV; Blessing, 1995)	h = −9→9
Tmin = 0.937, Tmax = 0.948	k = −12→14
11205 measured reflections	l = −18→18
4931 independent reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0368P)2 + 1.5007P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.088	(Δ/σ)max = 0.007
wR(F2) = 0.209	Δρmax = 0.33 e Å−3
S = 1.16	Δρmin = −0.28 e Å−3
4931 reflections	Extinction correction: none
362 parameters

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.

	x	y	z	Uiso*/Ueq
S1	−0.28532 (14)	0.36598 (9)	0.47963 (7)	0.0648 (3)
S2	−0.33244 (12)	0.21846 (9)	0.55311 (8)	0.0597 (3)
S3	0.2159 (2)	0.37139 (15)	0.72593 (9)	0.1008 (5)
S4	0.17109 (18)	0.22078 (14)	0.79400 (11)	0.0932 (5)
O1	−0.1425 (5)	0.7608 (3)	0.7099 (3)	0.0932 (11)
O2	−0.2430 (7)	0.6621 (3)	0.8270 (3)	0.1114 (15)
O3	0.5190 (4)	−0.0383 (3)	0.6160 (3)	0.1013 (14)
O4	0.4123 (4)	−0.1761 (3)	0.6849 (3)	0.0830 (10)
O5	0.3423 (6)	0.7628 (3)	0.9636 (3)	0.1124 (14)
O6	0.2541 (7)	0.6562 (3)	1.0807 (3)	0.1078 (13)
O7	1.0125 (5)	−0.0429 (5)	0.8735 (4)	0.143 (2)
O8	0.8920 (5)	−0.1686 (3)	0.9535 (3)	0.0985 (12)
N1	−0.2025 (5)	0.6797 (3)	0.7443 (3)	0.0695 (10)
N2	−0.2166 (5)	0.5481 (3)	0.5290 (3)	0.0675 (9)
N3	0.0258 (4)	0.1755 (2)	0.5594 (2)	0.0485 (7)
N4	0.3948 (4)	−0.0788 (3)	0.6427 (2)	0.0562 (8)
N5	0.2906 (5)	0.6772 (3)	0.9981 (3)	0.0765 (11)
N6	0.2519 (6)	0.5608 (4)	0.7817 (3)	0.0945 (15)
N7	0.5273 (5)	0.1785 (3)	0.8105 (3)	0.0725 (10)
N8	0.8822 (6)	−0.0777 (4)	0.9035 (3)	0.0798 (11)
C1	−0.2263 (5)	0.5991 (3)	0.6821 (3)	0.0536 (9)
C2	−0.2820 (6)	0.5018 (3)	0.7196 (3)	0.0607 (10)
H2	−0.3062	0.4877	0.784	0.073*
C3	−0.3013 (5)	0.4261 (3)	0.6612 (3)	0.0570 (9)
H3	−0.3366	0.3586	0.6846	0.078 (6)*
C4	−0.2670 (4)	0.4527 (3)	0.5671 (3)	0.0521 (9)
C5	−0.1959 (5)	0.6208 (3)	0.5874 (3)	0.0632 (11)
H5	−0.1598	0.6876	0.5627	0.078 (6)*
C6	−0.1129 (4)	0.1300 (3)	0.5804 (2)	0.0448 (7)
C7	−0.0971 (5)	0.0159 (3)	0.6229 (3)	0.0503 (8)
H7	−0.1982	−0.0121	0.6366	0.078 (6)*
C8	0.0692 (5)	−0.0546 (3)	0.6443 (3)	0.0483 (8)
H8	0.0851	−0.1316	0.6728	0.058*
C9	0.2126 (4)	−0.0072 (3)	0.6222 (2)	0.0425 (7)
C10	0.1881 (5)	0.1059 (3)	0.5803 (3)	0.0505 (8)
H10	0.2877	0.1353	0.5658	0.061*
C11	0.2288 (6)	0.4547 (4)	0.8158 (3)	0.0728 (13)
C12	0.2218 (6)	0.4174 (4)	0.9095 (3)	0.0706 (12)
H12	0.2054	0.3436	0.9313	0.078 (6)*
C13	0.2395 (6)	0.4909 (4)	0.9697 (3)	0.0691 (11)
H13	0.2342	0.4685	1.0337	0.083*
C14	0.2653 (6)	0.5984 (4)	0.9348 (3)	0.0680 (11)
C15	0.2697 (7)	0.6302 (5)	0.8413 (4)	0.0888 (16)
H15	0.286	0.7038	0.8184	0.107*
C16	0.3897 (6)	0.1317 (4)	0.8230 (3)	0.0690 (11)
C17	0.4031 (6)	0.0156 (4)	0.8614 (4)	0.0771 (13)
H17	0.3032	−0.0136	0.8688	0.078 (6)*
C18	0.5647 (6)	−0.0536 (4)	0.8877 (3)	0.0708 (11)
H18	0.5788	−0.1315	0.9137	0.085*
C19	0.7070 (5)	−0.0059 (3)	0.8749 (3)	0.0586 (9)
C20	0.6845 (6)	0.1087 (4)	0.8371 (3)	0.0686 (11)
H20	0.7831	0.1392	0.8298	0.082*

	U11	U22	U33	U12	U13	U23
S1	0.0590 (6)	0.0586 (6)	0.0625 (6)	0.0052 (5)	−0.0153 (5)	0.0013 (5)
S2	0.0394 (5)	0.0547 (6)	0.0817 (7)	−0.0040 (4)	−0.0121 (4)	−0.0117 (5)
S3	0.0942 (10)	0.1143 (11)	0.0657 (8)	0.0208 (8)	−0.0239 (7)	−0.0129 (7)
S4	0.0649 (8)	0.1047 (10)	0.1078 (11)	−0.0014 (7)	−0.0275 (7)	−0.0382 (8)
O1	0.090 (2)	0.0562 (18)	0.140 (3)	−0.0325 (17)	−0.023 (2)	0.0072 (19)
O2	0.192 (5)	0.070 (2)	0.087 (3)	−0.056 (3)	−0.024 (3)	−0.0074 (19)
O3	0.0428 (16)	0.090 (2)	0.167 (4)	−0.0267 (16)	−0.0314 (19)	0.040 (2)
O4	0.0621 (18)	0.0593 (18)	0.115 (3)	−0.0056 (14)	−0.0246 (17)	0.0246 (18)
O5	0.114 (3)	0.083 (2)	0.153 (4)	−0.057 (2)	−0.017 (3)	0.014 (2)
O6	0.157 (4)	0.080 (2)	0.092 (3)	−0.044 (3)	−0.017 (3)	−0.001 (2)
O7	0.064 (2)	0.148 (4)	0.205 (5)	−0.039 (3)	−0.031 (3)	0.056 (4)
O8	0.097 (3)	0.074 (2)	0.113 (3)	−0.0104 (19)	−0.024 (2)	0.013 (2)
N1	0.069 (2)	0.0378 (17)	0.103 (3)	−0.0172 (15)	−0.021 (2)	0.0058 (18)
N2	0.060 (2)	0.057 (2)	0.071 (2)	−0.0063 (16)	−0.0025 (17)	0.0161 (17)
N3	0.0421 (15)	0.0390 (14)	0.0646 (18)	−0.0129 (12)	−0.0090 (13)	0.0010 (13)
N4	0.0443 (17)	0.0510 (18)	0.072 (2)	−0.0121 (14)	−0.0162 (14)	0.0044 (15)
N5	0.071 (2)	0.057 (2)	0.097 (3)	−0.0150 (18)	−0.014 (2)	0.005 (2)
N6	0.095 (3)	0.092 (3)	0.064 (2)	0.003 (2)	−0.002 (2)	0.027 (2)
N7	0.072 (2)	0.065 (2)	0.076 (2)	−0.0121 (18)	−0.0121 (19)	−0.0057 (18)
N8	0.073 (3)	0.070 (2)	0.091 (3)	−0.016 (2)	−0.009 (2)	0.003 (2)
C1	0.0452 (19)	0.0357 (17)	0.075 (3)	−0.0060 (14)	−0.0102 (17)	0.0040 (16)
C2	0.074 (3)	0.0427 (19)	0.063 (2)	−0.0202 (18)	0.0015 (19)	0.0056 (17)
C3	0.067 (2)	0.0396 (18)	0.063 (2)	−0.0177 (17)	−0.0033 (18)	0.0037 (16)
C4	0.0350 (17)	0.0418 (18)	0.068 (2)	0.0017 (14)	−0.0067 (15)	0.0060 (16)
C5	0.054 (2)	0.045 (2)	0.084 (3)	−0.0157 (17)	−0.007 (2)	0.019 (2)
C6	0.0363 (16)	0.0450 (18)	0.0523 (19)	−0.0070 (13)	−0.0070 (14)	−0.0104 (14)
C7	0.0410 (18)	0.0476 (19)	0.065 (2)	−0.0199 (15)	−0.0026 (15)	−0.0033 (16)
C8	0.0481 (19)	0.0377 (17)	0.059 (2)	−0.0153 (14)	−0.0053 (15)	0.0011 (15)
C9	0.0374 (16)	0.0399 (16)	0.0516 (18)	−0.0112 (13)	−0.0096 (14)	−0.0039 (14)
C10	0.0406 (18)	0.0445 (18)	0.070 (2)	−0.0198 (15)	−0.0090 (16)	0.0027 (16)
C11	0.057 (2)	0.077 (3)	0.061 (2)	0.011 (2)	−0.0061 (19)	0.003 (2)
C12	0.082 (3)	0.061 (3)	0.060 (3)	−0.015 (2)	−0.001 (2)	0.005 (2)
C13	0.073 (3)	0.061 (2)	0.063 (3)	−0.013 (2)	−0.003 (2)	0.009 (2)
C14	0.055 (2)	0.061 (2)	0.075 (3)	−0.0069 (19)	−0.003 (2)	0.011 (2)
C15	0.091 (4)	0.072 (3)	0.081 (3)	−0.005 (3)	0.001 (3)	0.021 (3)
C16	0.063 (3)	0.075 (3)	0.068 (3)	−0.009 (2)	−0.006 (2)	−0.029 (2)
C17	0.061 (3)	0.083 (3)	0.096 (3)	−0.030 (2)	−0.001 (2)	−0.029 (3)
C18	0.072 (3)	0.059 (2)	0.084 (3)	−0.023 (2)	−0.002 (2)	−0.014 (2)
C19	0.057 (2)	0.059 (2)	0.059 (2)	−0.0137 (18)	−0.0014 (18)	−0.0117 (18)
C20	0.062 (3)	0.061 (2)	0.082 (3)	−0.018 (2)	−0.004 (2)	−0.005 (2)

S1—C4	1.781 (4)	C1—C2	1.372 (5)
S1—S2	2.0275 (15)	C2—C3	1.367 (6)
S2—C6	1.781 (3)	C2—H2	0.93
S3—C11	1.768 (5)	C3—C4	1.368 (5)
S3—S4	2.023 (2)	C3—H3	0.93
S4—C16	1.784 (5)	C5—H5	0.93
O1—N1	1.213 (4)	C6—C7	1.387 (5)
O2—N1	1.205 (5)	C7—C8	1.363 (5)
O3—N4	1.200 (4)	C7—H7	0.93
O4—N4	1.211 (4)	C8—C9	1.376 (4)
O5—N5	1.223 (5)	C8—H8	0.93
O6—N5	1.204 (5)	C9—C10	1.366 (4)
O7—N8	1.213 (5)	C10—H10	0.93
O8—N8	1.204 (5)	C11—C12	1.371 (6)
N1—C1	1.464 (6)	C12—C13	1.360 (6)
N2—C4	1.334 (5)	C12—H12	0.93
N2—C5	1.342 (6)	C13—C14	1.369 (6)
N3—C6	1.329 (4)	C13—H13	0.93
N3—C10	1.333 (4)	C14—C15	1.358 (7)
N4—C9	1.464 (4)	C15—H15	0.93
N5—C14	1.463 (6)	C16—C17	1.393 (6)
N6—C15	1.317 (8)	C17—C18	1.351 (6)
N6—C11	1.343 (6)	C17—H17	0.93
N7—C20	1.329 (6)	C18—C19	1.369 (6)
N7—C16	1.329 (6)	C18—H18	0.93
N8—C19	1.455 (6)	C19—C20	1.365 (5)
C1—C5	1.365 (6)	C20—H20	0.93
C4—S1—S2	104.06 (13)	C6—C7—H7	120.6
C6—S2—S1	103.36 (12)	C7—C8—C9	117.4 (3)
C11—S3—S4	104.51 (17)	C7—C8—H8	121.3
C16—S4—S3	104.02 (18)	C9—C8—H8	121.3
O2—N1—O1	123.3 (4)	C10—C9—C8	120.9 (3)
O2—N1—C1	118.6 (3)	C10—C9—N4	119.0 (3)
O1—N1—C1	118.2 (4)	C8—C9—N4	120.0 (3)
C4—N2—C5	117.4 (3)	N3—C10—C9	122.0 (3)
C6—N3—C10	117.2 (3)	N3—C10—H10	119
O3—N4—O4	123.5 (3)	C9—C10—H10	119
O3—N4—C9	118.3 (3)	N6—C11—C12	122.5 (5)
O4—N4—C9	118.1 (3)	N6—C11—S3	111.9 (4)
O6—N5—O5	123.8 (5)	C12—C11—S3	125.6 (4)
O6—N5—C14	118.2 (4)	C13—C12—C11	118.5 (4)
O5—N5—C14	117.9 (4)	C13—C12—H12	120.8
C15—N6—C11	118.0 (4)	C11—C12—H12	120.8
C20—N7—C16	116.7 (4)	C12—C13—C14	119.0 (4)
O8—N8—O7	123.4 (5)	C12—C13—H13	120.5
O8—N8—C19	119.3 (4)	C14—C13—H13	120.5
O7—N8—C19	117.3 (4)	C15—C14—C13	119.5 (5)
C5—C1—C2	119.9 (4)	C15—C14—N5	120.6 (5)
C5—C1—N1	120.7 (3)	C13—C14—N5	119.9 (4)
C2—C1—N1	119.4 (4)	N6—C15—C14	122.5 (5)
C3—C2—C1	119.1 (4)	N6—C15—H15	118.7
C3—C2—H2	120.5	C14—C15—H15	118.7
C1—C2—H2	120.5	N7—C16—C17	123.7 (4)
C2—C3—C4	117.8 (3)	N7—C16—S4	119.9 (4)
C2—C3—H3	121.1	C17—C16—S4	116.5 (4)
C4—C3—H3	121.1	C18—C17—C16	118.5 (4)
N2—C4—C3	124.1 (4)	C18—C17—H17	120.8
N2—C4—S1	111.2 (3)	C16—C17—H17	120.8
C3—C4—S1	124.7 (3)	C17—C18—C19	118.2 (4)
N2—C5—C1	121.7 (3)	C17—C18—H18	120.9
N2—C5—H5	119.2	C19—C18—H18	120.9
C1—C5—H5	119.2	C20—C19—C18	120.4 (4)
N3—C6—C7	123.6 (3)	C20—C19—N8	120.0 (4)
N3—C6—S2	119.2 (3)	C18—C19—N8	119.5 (4)
C7—C6—S2	117.3 (2)	N7—C20—C19	122.6 (4)
C8—C7—C6	118.8 (3)	N7—C20—H20	118.7
C8—C7—H7	120.6	C19—C20—H20	118.7
C4—S1—S2—C6	−80.13 (16)	N4—C9—C10—N3	179.7 (3)
C11—S3—S4—C16	−79.8 (2)	C15—N6—C11—C12	0.5 (7)
O2—N1—C1—C5	174.8 (4)	C15—N6—C11—S3	−177.8 (4)
O1—N1—C1—C5	−5.3 (5)	S4—S3—C11—N6	−177.7 (3)
O2—N1—C1—C2	−4.4 (6)	S4—S3—C11—C12	4.1 (4)
O1—N1—C1—C2	175.5 (4)	N6—C11—C12—C13	−0.2 (7)
C5—C1—C2—C3	1.8 (6)	S3—C11—C12—C13	177.9 (4)
N1—C1—C2—C3	−179.0 (4)	C11—C12—C13—C14	−0.6 (7)
C1—C2—C3—C4	−1.2 (6)	C12—C13—C14—C15	1.1 (7)
C5—N2—C4—C3	1.1 (5)	C12—C13—C14—N5	−178.0 (4)
C5—N2—C4—S1	−179.4 (3)	O6—N5—C14—C15	167.0 (5)
C2—C3—C4—N2	−0.2 (6)	O5—N5—C14—C15	−10.7 (7)
C2—C3—C4—S1	−179.7 (3)	O6—N5—C14—C13	−13.9 (6)
S2—S1—C4—N2	173.4 (2)	O5—N5—C14—C13	168.3 (4)
S2—S1—C4—C3	−7.1 (3)	C11—N6—C15—C14	−0.1 (8)
C4—N2—C5—C1	−0.5 (6)	C13—C14—C15—N6	−0.7 (8)
C2—C1—C5—N2	−0.9 (6)	N5—C14—C15—N6	178.4 (5)
N1—C1—C5—N2	179.9 (3)	C20—N7—C16—C17	−0.3 (7)
C10—N3—C6—C7	0.6 (5)	C20—N7—C16—S4	177.3 (3)
C10—N3—C6—S2	−179.4 (3)	S3—S4—C16—N7	9.5 (4)
S1—S2—C6—N3	6.6 (3)	S3—S4—C16—C17	−172.8 (3)
S1—S2—C6—C7	−173.5 (3)	N7—C16—C17—C18	0.1 (7)
N3—C6—C7—C8	−0.4 (6)	S4—C16—C17—C18	−177.6 (4)
S2—C6—C7—C8	179.6 (3)	C16—C17—C18—C19	−0.1 (7)
C6—C7—C8—C9	0.1 (5)	C17—C18—C19—C20	0.4 (7)
C7—C8—C9—C10	−0.1 (5)	C17—C18—C19—N8	179.2 (4)
C7—C8—C9—N4	−179.5 (3)	O8—N8—C19—C20	164.9 (4)
O3—N4—C9—C10	−5.0 (6)	O7—N8—C19—C20	−16.6 (7)
O4—N4—C9—C10	175.6 (4)	O8—N8—C19—C18	−14.0 (7)
O3—N4—C9—C8	174.3 (4)	O7—N8—C19—C18	164.5 (5)
O4—N4—C9—C8	−5.0 (5)	C16—N7—C20—C19	0.5 (7)
C6—N3—C10—C9	−0.6 (5)	C18—C19—C20—N7	−0.6 (7)
C8—C9—C10—N3	0.4 (6)	N8—C19—C20—N7	−179.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···S2	0.93	2.68	3.173 (4)	114
C8—H8···O1i	0.93	2.44	3.098 (5)	127
C12—H12···S4	0.93	2.70	3.189 (5)	113
C18—H18···O5i	0.93	2.50	3.171 (6)	129

Table 1

Selected torsion angles (°)

C4—S1—S2—C6	−80.13 (16)
C11—S3—S4—C16	−79.8 (2)
S2—S1—C4—N2	173.4 (2)
S2—S1—C4—C3	−7.1 (3)
S1—S2—C6—N3	6.6 (3)
S1—S2—C6—C7	−173.5 (3)
S4—S3—C11—N6	−177.7 (3)
S4—S3—C11—C12	4.1 (4)
S3—S4—C16—N7	9.5 (4)
S3—S4—C16—C17	−172.8 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯S2	0.93	2.68	3.173 (4)	114
C8—H8⋯O1i	0.93	2.44	3.098 (5)	127
C12—H12⋯S4	0.93	2.70	3.189 (5)	113
C18—H18⋯O5i	0.93	2.50	3.171 (6)	129

Symmetry code: (i) .