1,10-Phenanthroline-dithio-oxamide (2/1).

The asymmetric unit of the title compound, C(12)H(8)N(2)·0.5C(2)H(4)N(2)S(2), contains one 1,10-phenanthroline mol-ecule and a half-mol-ecule of dithio-oxamide, which lies across a crystallographic inversion center. The 1,10-phenanthroline unit is not strictly planar, with dihedral angles between the central benzene ring and the pyridine rings of 1.42 (10) and 1.40 (10)°. In the crystal structure, two 1,10-phenanthroline mol-ecules are linked together by one dithio-oxamide via inter-molecular N-H⋯N hydrogen bonds.

Related literature

For background to the chemistry of 1,10-phenanthroline, see: Goswami et al. (2005 ▶); Han et al. (2009 ▶); Ishida et al. (2010 ▶). For a related structure, see: Fun et al. (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C12H8N2·0.5C2H4N2S2

M = 240.30

Monoclinic,

a = 10.5481 (3) Å

b = 10.0544 (3) Å

c = 13.9960 (4) Å

β = 130.145 (2)°

V = 1134.65 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.28 × 0.26 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.931, T max = 0.974

22512 measured reflections

3374 independent reflections

2307 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.160

S = 1.07

3374 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.24 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016405/lh5039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016405/lh5039Isup2.hkl

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

C12H8N2·0.5C2H4N2S2	F(000) = 500
Mr = 240.30	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5115 reflections
a = 10.5481 (3) Å	θ = 2.5–30.1°
b = 10.0544 (3) Å	µ = 0.26 mm−1
c = 13.9960 (4) Å	T = 100 K
β = 130.145 (2)°	Block, orange
V = 1134.65 (6) Å3	0.28 × 0.26 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3374 independent reflections
Radiation source: fine-focus sealed tube	2307 reflections with I > 2σ(I)
graphite	Rint = 0.074
φ and ω scans	θmax = 30.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.931, Tmax = 0.974	k = −14→13
22512 measured reflections	l = −19→19

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0764P)2 + 0.8154P] where P = (Fo2 + 2Fc2)/3
3374 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 1.24 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1	0.3548 (2)	0.2611 (2)	0.34019 (17)	0.0185 (4)
N2	0.5551 (2)	0.4592 (2)	0.36522 (18)	0.0217 (4)
N3	0.8022 (2)	0.9404 (2)	0.36819 (19)	0.0201 (4)
C1	0.2582 (3)	0.1675 (2)	0.3304 (2)	0.0217 (5)
H1A	0.1591	0.1482	0.2512	0.026*
C2	0.2959 (3)	0.0962 (2)	0.4317 (2)	0.0234 (5)
H2A	0.2241	0.0313	0.4198	0.028*
C3	0.4421 (3)	0.1243 (3)	0.5494 (2)	0.0247 (5)
H3A	0.4698	0.0791	0.6186	0.030*
C4	0.5493 (3)	0.2219 (2)	0.5643 (2)	0.0193 (5)
C5	0.7051 (3)	0.2534 (3)	0.6845 (2)	0.0240 (5)
H5A	0.7382	0.2072	0.7549	0.029*
C6	0.8035 (3)	0.3489 (3)	0.6961 (2)	0.0236 (5)
H6A	0.9044	0.3670	0.7746	0.028*
C7	0.7561 (3)	0.4235 (2)	0.5902 (2)	0.0193 (5)
C8	0.8544 (3)	0.5272 (3)	0.6009 (2)	0.0248 (5)
H8A	0.9528	0.5508	0.6790	0.030*
C9	0.8045 (3)	0.5928 (3)	0.4964 (3)	0.0277 (6)
H9A	0.8688	0.6604	0.5015	0.033*
C10	0.6528 (3)	0.5553 (3)	0.3803 (2)	0.0267 (5)
H10A	0.6190	0.6011	0.3095	0.032*
C11	0.6054 (3)	0.3938 (2)	0.4689 (2)	0.0182 (5)
C12	0.4998 (3)	0.2896 (2)	0.4565 (2)	0.0170 (4)
C13	0.9644 (3)	0.9392 (2)	0.4567 (2)	0.0196 (5)
S1	1.08871 (7)	0.81821 (6)	0.47638 (6)	0.02354 (18)
H3C	0.752 (4)	0.884 (3)	0.314 (3)	0.030 (8)*
H3B	0.754 (4)	1.004 (3)	0.366 (3)	0.032 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0163 (8)	0.0198 (10)	0.0163 (9)	−0.0001 (7)	0.0091 (7)	−0.0012 (7)
N2	0.0213 (9)	0.0205 (10)	0.0208 (9)	−0.0015 (8)	0.0125 (8)	0.0007 (8)
N3	0.0170 (9)	0.0203 (11)	0.0173 (9)	−0.0006 (8)	0.0085 (8)	−0.0037 (8)
C1	0.0182 (9)	0.0207 (12)	0.0216 (11)	−0.0002 (9)	0.0108 (9)	−0.0009 (9)
C2	0.0224 (10)	0.0200 (12)	0.0290 (12)	−0.0002 (9)	0.0171 (10)	0.0038 (10)
C3	0.0234 (11)	0.0260 (13)	0.0237 (12)	0.0047 (9)	0.0148 (10)	0.0081 (10)
C4	0.0183 (9)	0.0211 (12)	0.0172 (10)	0.0025 (8)	0.0108 (8)	0.0014 (9)
C5	0.0203 (10)	0.0314 (14)	0.0149 (10)	0.0062 (9)	0.0090 (9)	0.0033 (10)
C6	0.0184 (10)	0.0304 (14)	0.0152 (10)	0.0028 (9)	0.0078 (9)	−0.0042 (9)
C7	0.0154 (9)	0.0196 (12)	0.0200 (11)	0.0023 (8)	0.0101 (8)	−0.0039 (9)
C8	0.0147 (9)	0.0235 (13)	0.0285 (12)	−0.0012 (8)	0.0104 (9)	−0.0049 (10)
C9	0.0230 (11)	0.0205 (13)	0.0401 (15)	−0.0037 (9)	0.0206 (11)	−0.0027 (11)
C10	0.0255 (11)	0.0250 (13)	0.0280 (12)	−0.0015 (10)	0.0166 (10)	0.0028 (10)
C11	0.0165 (9)	0.0186 (12)	0.0177 (10)	0.0012 (8)	0.0103 (8)	−0.0010 (9)
C12	0.0172 (9)	0.0160 (11)	0.0164 (10)	0.0021 (8)	0.0102 (8)	−0.0007 (8)
C13	0.0205 (10)	0.0239 (13)	0.0157 (10)	−0.0008 (9)	0.0122 (9)	0.0015 (9)
S1	0.0235 (3)	0.0213 (3)	0.0248 (3)	0.0033 (2)	0.0151 (2)	−0.0009 (2)

N1—C1	1.328 (3)	C5—C6	1.344 (4)
N1—C12	1.364 (3)	C5—H5A	0.9300
N2—C10	1.326 (3)	C6—C7	1.433 (3)
N2—C11	1.352 (3)	C6—H6A	0.9300
N3—C13	1.315 (3)	C7—C8	1.408 (3)
N3—H3C	0.81 (3)	C7—C11	1.420 (3)
N3—H3B	0.81 (3)	C8—C9	1.364 (4)
C1—C2	1.398 (3)	C8—H8A	0.9300
C1—H1A	0.9300	C9—C10	1.411 (3)
C2—C3	1.377 (3)	C9—H9A	0.9300
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.407 (3)	C11—C12	1.456 (3)
C3—H3A	0.9300	C13—C13i	1.535 (5)
C4—C12	1.412 (3)	C13—S1	1.676 (2)
C4—C5	1.438 (3)
C1—N1—C12	117.8 (2)	C7—C6—H6A	119.3
C10—N2—C11	117.2 (2)	C8—C7—C11	117.5 (2)
C13—N3—H3C	123 (2)	C8—C7—C6	122.4 (2)
C13—N3—H3B	117 (2)	C11—C7—C6	120.1 (2)
H3C—N3—H3B	120 (3)	C9—C8—C7	119.7 (2)
N1—C1—C2	124.2 (2)	C9—C8—H8A	120.1
N1—C1—H1A	117.9	C7—C8—H8A	120.1
C2—C1—H1A	117.9	C8—C9—C10	118.2 (2)
C3—C2—C1	118.3 (2)	C8—C9—H9A	120.9
C3—C2—H2A	120.8	C10—C9—H9A	120.9
C1—C2—H2A	120.8	N2—C10—C9	124.5 (2)
C2—C3—C4	119.6 (2)	N2—C10—H10A	117.8
C2—C3—H3A	120.2	C9—C10—H10A	117.8
C4—C3—H3A	120.2	N2—C11—C7	122.9 (2)
C3—C4—C12	118.0 (2)	N2—C11—C12	118.79 (19)
C3—C4—C5	122.0 (2)	C7—C11—C12	118.3 (2)
C12—C4—C5	120.0 (2)	N1—C12—C4	122.1 (2)
C6—C5—C4	120.7 (2)	N1—C12—C11	118.4 (2)
C6—C5—H5A	119.7	C4—C12—C11	119.46 (19)
C4—C5—H5A	119.7	N3—C13—C13i	114.4 (3)
C5—C6—C7	121.4 (2)	N3—C13—S1	124.50 (19)
C5—C6—H6A	119.3	C13i—C13—S1	121.1 (2)
C12—N1—C1—C2	−0.2 (3)	C10—N2—C11—C12	178.7 (2)
N1—C1—C2—C3	0.2 (4)	C8—C7—C11—N2	0.9 (3)
C1—C2—C3—C4	−0.7 (4)	C6—C7—C11—N2	−179.0 (2)
C2—C3—C4—C12	1.3 (4)	C8—C7—C11—C12	−178.2 (2)
C2—C3—C4—C5	−178.6 (2)	C6—C7—C11—C12	1.9 (3)
C3—C4—C5—C6	−178.7 (2)	C1—N1—C12—C4	0.8 (3)
C12—C4—C5—C6	1.4 (4)	C1—N1—C12—C11	−178.8 (2)
C4—C5—C6—C7	0.8 (4)	C3—C4—C12—N1	−1.3 (3)
C5—C6—C7—C8	177.7 (2)	C5—C4—C12—N1	178.6 (2)
C5—C6—C7—C11	−2.4 (3)	C3—C4—C12—C11	178.2 (2)
C11—C7—C8—C9	−1.3 (3)	C5—C4—C12—C11	−1.8 (3)
C6—C7—C8—C9	178.6 (2)	N2—C11—C12—N1	0.7 (3)
C7—C8—C9—C10	1.2 (4)	C7—C11—C12—N1	179.81 (19)
C11—N2—C10—C9	0.3 (4)	N2—C11—C12—C4	−178.9 (2)
C8—C9—C10—N2	−0.7 (4)	C7—C11—C12—C4	0.2 (3)
C10—N2—C11—C7	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3C···N1ii	0.81 (3)	2.08 (3)	2.876 (3)	167 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3C⋯N1i	0.81 (3)	2.08 (3)	2.876 (3)	167 (4)

Symmetry code: (i) .