2,2′-(Diselane-1,2-di­yl)dinicotinamide N,N′-dimethyl­formamide disolvate

Feng, A.; Xu, Y.; Wei, X.

doi:10.1107/S1600536810015047

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1216

https://doi.org/10.1107/S1600536810015047

Open

access

2,2′-(Diselane-1,2-diyl)dinicotinamide N,N′-dimethylformamide disolvate

Aixia Feng,^a Ying Xu ^a and Xuehong Wei ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shanxi University, Shanxi Province, People's Republic of China
^*Correspondence e-mail: xhwei@sxu.edu.cn

(Received 23 March 2010; accepted 24 April 2010; online 30 April 2010)

The asymmetric unit of the title compound, C₁₂H₁₀N₄O₂Se₂·2C₃H₇NO, contains two solvent molecules and two half molecules of the dinicotinamide, each of which sits on a center of symmetry passing through the middle of the Se—Se bond. In each molecule, 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 molecules). Intermolecular 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_r = 546.34
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.03
3937 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.73 e Å⁻³

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) -x, -y+1, -z+1.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015047/fl2299Isup2.hkl

checkCIF report

Comment top

Organoselenium compounds have attracted much atention because of their potential applications in organic synthesis, precursors for semiconducting materials, ligand chemistry and biochemistry (Mugesh et al., 2001). During the past decade, many organoselenium compounds have been synthesized and well characterized. In contrast to alkyl, aryl, and mixed alkylaryl senium compounds, the pyridyl selenium compounds are still rare.

The unit cell contains two nicotinamide molecules and four of the solvent molecules. The asymmetric unit contains two solvent molecules and two half molecues of the nicotinamide each of which sits on a center of symmetry passing through the middle of the Se—Se bond (Fig. 1). In (I),the two independent nicotinamides (molecule A containing Se1 and molecule B containing Se2) have comparable conformations. In each nicotinamide, the two pyridyl groups and the diseleno group are approximately coplanar (r.m.s. deviations from planarity for all non-H atoms are 0.011 and 0.008Å for molecules A and B, respectively while the two CONH₂ groups are rotated out of this plane by 11.0 (5)° and 18.6 (5)° for molecules A and B, respectively. Fig. 2 shows the sheets of molecules formed by intermolecular N-H···O hydrogen-bond interactions between the nicotinamides and neighbouring solvents with distances between 2.869 (5) and 3.081 (4) Å (Table 1).

The structure of (I) is similar to that of other diselenide compounds (Kienitz, et al. 1996; Bhasin and Singh 2002).The two neighbouring pyridyl groups can be brought into register by rotation about the Se—Se bond. The commonly observed approximate coplanarity of the rings and the Se—Se bonds (C—C—Se—Se or N—C—Se—Se torsion angles ca. 0°) in these molecules has been explained in terms of a minimization of Se···Se lone pair repulsion.

Related literature top

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 top

To a vigorously stirred solution of selenium powder (1.19 g, 15 mmol) and absolute ethanol (30 ml), sodium borohydride (0.40 g, 10.6 mmol) was added at 0 °C. The mixture was warmed to room temperature and stirred for 2 h. 2-Chloro-nicotinamide (1.56 g, 10 mmol) was added and stirred for 7 days. O₂ was passed through the solution slowly for 2 h after the reaction mixture was acidfied by glacial acetic. The solvents were removed in vacuo and the residue was extracted with hot dimethyl sulphoxide (DMSO) and filtered. The filtrate was poured into water( 200 ml, cooled to 0 °C). The precipitate was separated by filtration and recrystallized from DMSO-CH₃OH(1:2) to give the product as yellow crystals, yield: 1.56 g, 78%; m.p. 124-125 °C. ¹H-NMR ( 300 MHz, DCCl₃) δ (ppm): 7.27 (d, 2H), 7.81 (s, 2H), 8.14 (d, 2H), 8.32 (s, 2H), 8.48 (s, 2H), 8.65 (s, 2H);⁷⁷Se-NMR (57 MHz, DMSO-d₆ ) δ(ppm): 524.77.

Structure description top

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).

Computing details top

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

Figures top

Fig. 1. Structure showing 50 % probability.

2,2'-(Diselane-1,2-diyl)dinicotinamide N,N'-dimethylformamide disolvate top

Crystal data top

C₁₂H₁₀N₄O₂Se₂·2C₃H₇NO	Z = 2
M_r = 546.34	F(000) = 548
Triclinic, P1	D_x = 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

Data collection top

Siemens SMART CCD diffractometer	3937 independent reflections
Radiation source: fine-focus sealed tube	3359 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.439, T_max = 0.560	k = −14→13
3937 measured reflections	l = 0→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0416P)² + 0.7097P] where P = (F_o² + 2F_c²)/3
3937 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₁₂H₁₀N₄O₂Se₂·2C₃H₇NO	γ = 95.833 (3)°
M_r = 546.34	V = 1139.3 (4) Å³
Triclinic, P1	Z = 2
a = 7.6101 (17) Å	Mo Kα radiation
b = 12.318 (3) Å	µ = 3.28 mm⁻¹
c = 13.420 (3) Å	T = 298 K
α = 114.175 (2)°	0.30 × 0.20 × 0.20 mm
β = 91.017 (3)°

Data collection top

Siemens SMART CCD diffractometer	3937 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3359 reflections with I > 2σ(I)
T_min = 0.439, T_max = 0.560	R_int = 0.000
3937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
3937 reflections	Δρ_min = −0.73 e Å⁻³
275 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₄O₂Se₂·2C₃H₇NO
M_r	546.34
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.6101 (17), 12.318 (3), 13.420 (3)
α, β, γ (°)	114.175 (2), 91.017 (3), 95.833 (3)
V (Å³)	1139.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.28
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Siemens SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.439, 0.560
No. of measured, independent and observed [I > 2σ(I)] reflections	3937, 3937, 3359
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.03
No. of reflections	3937
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.73

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.86	2.09	2.946 (4)	170.0
N1—H1B···O3	0.86	2.03	2.869 (5)	163.2
N3—H3B···O4	0.86	2.10	2.919 (4)	157.9
N3—H3A···O1ⁱ	0.86	2.31	3.081 (4)	149.8

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

We thank the SNSF (Nos. 2008011021 and 2008012013-2) and the Homecoming Foundation of Shanxi Province for support.

References

Bhasin, K. K. & Singh, J. (2002). J. Organomet. Chem. 658, 71–76. Web of Science CSD CrossRef CAS Google Scholar
Kienitz, C. O., Tho1ne, C., and Jones. P. G. (1996). Inorg. Chem. 35, 3990–3997. Google Scholar
Mugesh, G., Mont, W.-W. & Sies, H. (2001). Chem. Rev. 101, 2125–2179. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar