2,2'-(Diselane-1,2-di-yl)dinicotinamide N,N'-dimethyl-formamide disolvate.

The asymmetric unit of the title compound, C(12)H(10)N(4)O(2)Se(2)·2C(3)H(7)NO, contains two solvent mol-ecules and two half mol-ecules of the dinicotinamide, each of which sits on a center of symmetry passing through the middle of the Se-Se bond. In each mol-ecule, the two pyridyl groups and diseleno group are approximately coplanar (r.m.s. deviations from planarity for all non-H atoms = 0.011 and 0.008 Å in the two mol-ecules). Inter-molecular N-H⋯O hydrogen bonds stablilize the crystal packing.

Related literature

For the potential applications of organoselenium compounds in organic synthesis, as precursors for semiconducting materials and in ligand chemistry and biochemistry, see: Mugesh et al. (2001 ▶). For related diselenide compounds, see: Bhasin & Singh (2002 ▶); Kienitz et al. (1996 ▶).

Experimental

Crystal data

C12H10N4O2Se2·2C3H7NO

M = 546.34

Triclinic,

a = 7.6101 (17) Å

b = 12.318 (3) Å

c = 13.420 (3) Å

α = 114.175 (2)°

β = 91.017 (3)°

γ = 95.833 (3)°

V = 1139.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 3.28 mm−1

T = 298 K

0.30 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.439, T max = 0.560

3937 measured reflections

3937 independent reflections

3359 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.03

3937 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.73 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015047/fl2299sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015047/fl2299Isup2.hkl

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

C12H10N4O2Se2·2C3H7NO	Z = 2
Mr = 546.34	F(000) = 548
Triclinic, P1	Dx = 1.593 Mg m−3
a = 7.6101 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.318 (3) Å	Cell parameters from 2815 reflections
c = 13.420 (3) Å	θ = 3.1–27.5°
α = 114.175 (2)°	µ = 3.28 mm−1
β = 91.017 (3)°	T = 298 K
γ = 95.833 (3)°	Block, yellow
V = 1139.3 (4) Å3	0.30 × 0.20 × 0.20 mm

Siemens SMART CCD diffractometer	3937 independent reflections
Radiation source: fine-focus sealed tube	3359 reflections with I > 2σ(I)
graphite	Rint = 0.0000
phi and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.439, Tmax = 0.560	k = −14→13
3937 measured reflections	l = 0→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.7097P] where P = (Fo2 + 2Fc2)/3
3937 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.73 e Å−3

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
Se1	0.44747 (5)	0.90079 (3)	0.43528 (3)	0.04343 (13)
Se2	−0.00660 (5)	0.90803 (3)	0.92023 (2)	0.04228 (13)
N1	0.1532 (5)	0.5410 (3)	0.7795 (2)	0.0635 (10)
H1A	0.1427	0.5036	0.7093	0.076*
H1B	0.2126	0.5139	0.8176	0.076*
N2	0.0893 (4)	0.8848 (2)	1.1107 (2)	0.0425 (7)
N3	0.2600 (5)	0.5278 (3)	0.3920 (3)	0.0592 (9)
H3A	0.2117	0.4794	0.3289	0.071*
H3B	0.2580	0.5066	0.4457	0.071*
N4	0.5588 (4)	0.9107 (3)	0.6373 (2)	0.0486 (7)
N5	0.3752 (5)	0.2618 (4)	0.9343 (3)	0.0708 (10)
N6	0.0494 (5)	0.2208 (3)	0.4807 (2)	0.0551 (8)
O1	−0.0074 (4)	0.6808 (2)	0.77632 (19)	0.0673 (9)
O2	0.3436 (5)	0.6689 (2)	0.3326 (2)	0.0745 (9)
O3	0.3116 (6)	0.4039 (4)	0.8778 (3)	0.1119 (15)
O4	0.1655 (4)	0.4149 (2)	0.5403 (2)	0.0636 (8)
C1	0.0787 (5)	0.6393 (3)	0.8283 (3)	0.0453 (8)
C2	0.0992 (4)	0.7021 (3)	0.9497 (2)	0.0385 (7)
C3	0.1484 (5)	0.6470 (3)	1.0157 (3)	0.0444 (8)
H3	0.1689	0.5671	0.9840	0.053*
C4	0.1672 (5)	0.7094 (3)	1.1279 (3)	0.0501 (9)
H4	0.1983	0.6727	1.1728	0.060*
C5	0.1388 (5)	0.8271 (3)	1.1708 (3)	0.0481 (9)
H5	0.1547	0.8700	1.2463	0.058*
C6	0.0676 (4)	0.8226 (3)	1.0022 (2)	0.0359 (7)
C7	0.3379 (5)	0.6354 (3)	0.4068 (3)	0.0485 (9)
C8	0.4199 (5)	0.7156 (3)	0.5172 (3)	0.0415 (8)
C9	0.4458 (6)	0.6768 (3)	0.5990 (3)	0.0555 (10)
H9	0.4074	0.5980	0.5869	0.067*
C10	0.5283 (6)	0.7548 (4)	0.6982 (3)	0.0649 (12)
H10	0.5460	0.7299	0.7539	0.078*
C11	0.5836 (6)	0.8695 (4)	0.7131 (3)	0.0597 (11)
H11	0.6417	0.9216	0.7797	0.072*
C12	0.4806 (4)	0.8354 (3)	0.5408 (3)	0.0382 (7)
C13	0.4094 (8)	0.1434 (5)	0.9066 (7)	0.132 (3)
H13A	0.3984	0.0998	0.8285	0.198*
H13B	0.3259	0.1059	0.9390	0.198*
H13C	0.5273	0.1436	0.9334	0.198*
C14	0.3803 (8)	0.3421 (6)	1.0492 (5)	0.1017 (18)
H14A	0.3586	0.4203	1.0564	0.153*
H14B	0.4947	0.3471	1.0833	0.153*
H14C	0.2910	0.3120	1.0842	0.153*
C15	0.3437 (7)	0.3039 (5)	0.8611 (4)	0.0867 (15)
H15	0.3463	0.2508	0.7882	0.104*
C16	−0.0269 (7)	0.1122 (4)	0.3893 (4)	0.0864 (16)
H16A	−0.0493	0.1295	0.3270	0.130*
H16B	−0.1361	0.0820	0.4089	0.130*
H16C	0.0541	0.0530	0.3715	0.130*
C17	0.0853 (7)	0.2161 (4)	0.5860 (4)	0.0791 (14)
H17A	0.1766	0.2791	0.6280	0.119*
H17B	0.1233	0.1400	0.5741	0.119*
H17C	−0.0205	0.2260	0.6252	0.119*
C18	0.0939 (6)	0.3203 (4)	0.4690 (3)	0.0571 (10)
H18	0.0690	0.3193	0.4005	0.069*

	U11	U22	U33	U12	U13	U23
Se1	0.0546 (2)	0.0391 (2)	0.0405 (2)	−0.00010 (15)	−0.00515 (15)	0.02201 (17)
Se2	0.0608 (2)	0.0352 (2)	0.02975 (19)	0.00734 (15)	−0.00560 (15)	0.01226 (15)
N1	0.103 (3)	0.051 (2)	0.0322 (15)	0.0285 (19)	−0.0013 (16)	0.0088 (14)
N2	0.0567 (18)	0.0399 (16)	0.0296 (14)	0.0083 (13)	−0.0010 (12)	0.0127 (12)
N3	0.084 (2)	0.0411 (18)	0.0469 (17)	−0.0106 (16)	−0.0191 (16)	0.0181 (15)
N4	0.062 (2)	0.0385 (16)	0.0464 (17)	−0.0001 (14)	−0.0092 (14)	0.0207 (14)
N5	0.062 (2)	0.079 (3)	0.081 (3)	0.0151 (19)	0.0075 (19)	0.041 (2)
N6	0.074 (2)	0.0438 (18)	0.0476 (18)	0.0091 (15)	0.0171 (16)	0.0181 (15)
O1	0.113 (2)	0.0510 (16)	0.0310 (12)	0.0239 (16)	−0.0190 (14)	0.0072 (12)
O2	0.125 (3)	0.0538 (17)	0.0457 (15)	−0.0128 (17)	−0.0233 (16)	0.0281 (14)
O3	0.153 (4)	0.094 (3)	0.108 (3)	0.067 (3)	0.014 (3)	0.049 (2)
O4	0.097 (2)	0.0467 (16)	0.0417 (14)	−0.0024 (14)	0.0025 (14)	0.0150 (13)
C1	0.067 (2)	0.0349 (18)	0.0308 (16)	0.0060 (16)	−0.0036 (16)	0.0105 (14)
C2	0.0447 (19)	0.0359 (18)	0.0297 (16)	0.0021 (14)	−0.0026 (13)	0.0090 (14)
C3	0.057 (2)	0.0401 (19)	0.0380 (18)	0.0119 (16)	0.0013 (15)	0.0168 (15)
C4	0.067 (2)	0.053 (2)	0.0384 (18)	0.0134 (18)	0.0000 (17)	0.0252 (17)
C5	0.065 (2)	0.050 (2)	0.0280 (16)	0.0102 (17)	0.0010 (15)	0.0142 (16)
C6	0.0424 (18)	0.0341 (17)	0.0315 (16)	0.0016 (13)	−0.0021 (13)	0.0148 (14)
C7	0.060 (2)	0.041 (2)	0.0445 (19)	0.0041 (16)	−0.0108 (16)	0.0180 (16)
C8	0.048 (2)	0.0393 (18)	0.0399 (18)	0.0020 (15)	−0.0030 (15)	0.0198 (15)
C9	0.080 (3)	0.040 (2)	0.051 (2)	−0.0009 (18)	−0.0083 (19)	0.0255 (18)
C10	0.101 (3)	0.052 (2)	0.046 (2)	−0.004 (2)	−0.019 (2)	0.0288 (19)
C11	0.081 (3)	0.052 (2)	0.044 (2)	−0.001 (2)	−0.0196 (19)	0.0210 (19)
C12	0.0416 (18)	0.0377 (18)	0.0389 (17)	0.0032 (14)	−0.0027 (14)	0.0200 (15)
C13	0.086 (4)	0.098 (5)	0.256 (9)	0.029 (3)	0.059 (5)	0.112 (6)
C14	0.077 (4)	0.134 (5)	0.101 (4)	−0.006 (3)	0.000 (3)	0.061 (4)
C15	0.088 (4)	0.097 (4)	0.076 (3)	0.030 (3)	0.008 (3)	0.033 (3)
C16	0.102 (4)	0.050 (3)	0.081 (3)	−0.009 (2)	0.031 (3)	0.004 (2)
C17	0.089 (4)	0.091 (4)	0.086 (3)	0.016 (3)	0.012 (3)	0.064 (3)
C18	0.080 (3)	0.055 (2)	0.0370 (19)	0.007 (2)	0.0086 (18)	0.0202 (19)

Se1—C12	1.918 (3)	C3—C4	1.379 (5)
Se1—Se1i	2.3889 (8)	C3—H3	0.9300
Se2—C6	1.919 (3)	C4—C5	1.365 (5)
Se2—Se2ii	2.3877 (7)	C4—H4	0.9300
N1—C1	1.312 (4)	C5—H5	0.9300
N1—H1A	0.8600	C7—C8	1.484 (5)
N1—H1B	0.8600	C8—C9	1.383 (5)
N2—C6	1.336 (4)	C8—C12	1.403 (5)
N2—C5	1.346 (4)	C9—C10	1.375 (5)
N3—C7	1.330 (5)	C9—H9	0.9300
N3—H3A	0.8600	C10—C11	1.363 (5)
N3—H3B	0.8600	C10—H10	0.9300
N4—C11	1.328 (5)	C11—H11	0.9300
N4—C12	1.330 (4)	C13—H13A	0.9600
N5—C15	1.313 (6)	C13—H13B	0.9600
N5—C13	1.403 (6)	C13—H13C	0.9600
N5—C14	1.449 (7)	C14—H14A	0.9600
N6—C18	1.311 (5)	C14—H14B	0.9600
N6—C16	1.451 (5)	C14—H14C	0.9600
N6—C17	1.460 (5)	C15—H15	0.9300
O1—C1	1.233 (4)	C16—H16A	0.9600
O2—C7	1.224 (4)	C16—H16B	0.9600
O3—C15	1.210 (6)	C16—H16C	0.9600
O4—C18	1.229 (5)	C17—H17A	0.9600
C1—C2	1.487 (4)	C17—H17B	0.9600
C2—C3	1.385 (4)	C17—H17C	0.9600
C2—C6	1.406 (4)	C18—H18	0.9300
C12—Se1—Se1i	92.21 (10)	C10—C9—H9	120.1
C6—Se2—Se2ii	92.67 (9)	C8—C9—H9	120.1
C1—N1—H1A	120.0	C11—C10—C9	118.6 (3)
C1—N1—H1B	120.0	C11—C10—H10	120.7
H1A—N1—H1B	120.0	C9—C10—H10	120.7
C6—N2—C5	117.6 (3)	N4—C11—C10	123.3 (4)
C7—N3—H3A	120.0	N4—C11—H11	118.3
C7—N3—H3B	120.0	C10—C11—H11	118.3
H3A—N3—H3B	120.0	N4—C12—C8	122.6 (3)
C11—N4—C12	118.4 (3)	N4—C12—Se1	116.3 (2)
C15—N5—C13	123.2 (5)	C8—C12—Se1	121.1 (2)
C15—N5—C14	118.6 (5)	N5—C13—H13A	109.5
C13—N5—C14	118.2 (5)	N5—C13—H13B	109.5
C18—N6—C16	121.4 (4)	H13A—C13—H13B	109.5
C18—N6—C17	119.9 (4)	N5—C13—H13C	109.5
C16—N6—C17	118.6 (4)	H13A—C13—H13C	109.5
O1—C1—N1	121.8 (3)	H13B—C13—H13C	109.5
O1—C1—C2	119.4 (3)	N5—C14—H14A	109.5
N1—C1—C2	118.8 (3)	N5—C14—H14B	109.5
C3—C2—C6	117.2 (3)	H14A—C14—H14B	109.5
C3—C2—C1	122.8 (3)	N5—C14—H14C	109.5
C6—C2—C1	120.0 (3)	H14A—C14—H14C	109.5
C4—C3—C2	120.6 (3)	H14B—C14—H14C	109.5
C4—C3—H3	119.7	O3—C15—N5	127.4 (5)
C2—C3—H3	119.7	O3—C15—H15	116.3
C5—C4—C3	117.8 (3)	N5—C15—H15	116.3
C5—C4—H4	121.1	N6—C16—H16A	109.5
C3—C4—H4	121.1	N6—C16—H16B	109.5
N2—C5—C4	124.0 (3)	H16A—C16—H16B	109.5
N2—C5—H5	118.0	N6—C16—H16C	109.5
C4—C5—H5	118.0	H16A—C16—H16C	109.5
N2—C6—C2	122.7 (3)	H16B—C16—H16C	109.5
N2—C6—Se2	116.1 (2)	N6—C17—H17A	109.5
C2—C6—Se2	121.2 (2)	N6—C17—H17B	109.5
O2—C7—N3	122.0 (3)	H17A—C17—H17B	109.5
O2—C7—C8	120.0 (3)	N6—C17—H17C	109.5
N3—C7—C8	118.0 (3)	H17A—C17—H17C	109.5
C9—C8—C12	117.2 (3)	H17B—C17—H17C	109.5
C9—C8—C7	123.0 (3)	O4—C18—N6	125.9 (4)
C12—C8—C7	119.8 (3)	O4—C18—H18	117.0
C10—C9—C8	119.9 (3)	N6—C18—H18	117.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.86	2.09	2.946 (4)	170
N1—H1B···O3	0.86	2.03	2.869 (5)	163
N3—H3B···O4	0.86	2.10	2.919 (4)	158
N3—H3A···O1iii	0.86	2.31	3.081 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4	0.86	2.09	2.946 (4)	170
N1—H1B⋯O3	0.86	2.03	2.869 (5)	163
N3—H3B⋯O4	0.86	2.10	2.919 (4)	158
N3—H3A⋯O1i	0.86	2.31	3.081 (4)	150

Symmetry code: (i) .