4,4′-Bipyridine–3,3′-disulfanediyl­bis­(1H-1,2,4-triazole-5-amine) (1/1)

Yang, W.; Qiu, Q.-M.; Jin, Q.-H.; Zhang, C.-L.

doi:10.1107/S1600536812042742

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3194

doi:10.1107/S1600536812042742

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4,4′-Bipyridine–3,3′-disulfanediylbis(1H-1,2,4-triazole-5-amine) (1/1)

Wei Yang,^a Qi-Ming Qiu,^a Qiong-Hua Jin ^a ^* and Cun-Lin Zhang ^b

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, and ^bKey Laboratory of Terahertz Optoelectronics, Ministry of Education, Department of Physics, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: jinqh204@163.com

(Received 15 August 2012; accepted 12 October 2012; online 20 October 2012)

In the title 1:1 adduct, C₁₀H₈N₂·C₄H₆N₈S₂·, the components are connected through N—H⋯N hydrogen bonds, leading to a two-dimensional structure. The C—S—S—C torsion angle is −83.6 (1)°. The dihedral angle between pyridine rings is 1.86 (15)°.

Related literature

For structures containing 1H-1,2,4-triazole-5-amine-3-thiolate, see: Aldoshin et al. (2003 ); Hao et al. (2010 ); Rakova et al. (2003 ). For related structures, see: Brito et al. (2007 ); Deng et al. (2005 ).

Experimental

Crystal data

C₁₀H₈N₂·C₄H₆N₈S₂
M_r = 386.47
Triclinic, $[P \overline 1]$
a = 9.324 (1) Å
b = 9.4540 (11) Å
c = 11.3840 (13) Å
α = 109.560 (2)°
β = 104.089 (1)°
γ = 105.627 (1)°
V = 846.86 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 298 K
0.35 × 0.30 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.891, T_max = 0.933
4439 measured reflections
2952 independent reflections
2121 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.106
S = 1.04
2952 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1ⁱ	0.86	2.22	2.850 (3)	131
N4—H4A⋯N5ⁱ	0.86	2.29	3.058 (3)	149
N4—H4B⋯N10ⁱⁱ	0.86	2.18	2.977 (3)	154
N6—H6⋯N9ⁱⁱⁱ	0.86	2.04	2.867 (3)	162
N8—H8A⋯N3^iv	0.86	2.33	3.137 (3)	156
N8—H8B⋯N7^v	0.86	2.22	3.068 (3)	167
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y, -z; (iv) x, y-1, z; (v) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042742/qm2081sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042742/qm2081Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042742/qm2081Isup3.cml

checkCIF report

Comment top

The design and synthesis of novel inorganic-organic hybrid coordination complexes have attracted the attention of many chemists in recent years. So far, there are very few literature reports of structures containing 1H-1,2,4-triazole-5-amine-3-thiolate (Rakova et al.2003; Hao et al., 2010; Aldoshin et al., 2003). We are interested in synthesizing new transition metal complexes containing 5-AMT. The title co-crystal was unexpectedly obtained in the course of synthesizing 5-AMT-Ni(II) complexes.

The molecular structure of the co-crystal is shown in Fig.1. The title compound is triclinic in the P-1 space group. C₄H₆N₈S₂.C₁₀H₈N₂ contains two 5-AMT units linked by an S—S disulfide bridge. The C—S—S—C torsion angle is 83.6 (1)°. This value is close to that of 81.9 (1)° determined for 5,5'-Dithiobis(1-phenyl-1H-tetrazole) (Brito et al., 2007). The 4,4'-bipyridine molecule is connected to a C₄H₆N₈S₂ molecule through N—H···N hydrogen bonds, which are similar to those in the co-crystal of C₁₀H₈N₂.2C₂H₃N₃S₂ (Deng et al., 2005). Further N—H···N hydrogen bonds between C₄H₆N₈S₂ molecules leads to a two-dimensional network (Fig.2 and Fig.3). There are face-to-face πi-πi stacking interactions between the 4,4'-bipyridine and triazole rings, the centroid-centroid distance is 3.630 Å.

Related literature top

For structures containing 1H-1,2,4-triazole-5-amine-3-thiolate, see: Aldoshin et al. (2003); Hao et al. (2010); Rakova et al. (2003). For related structures, see: Brito et al. (2007); Deng et al. (2005).

Experimental top

The title co-crystal has been prepared by adding 5-AMT(1.8 mmol), sodium hydroxide(1.2 mmol) and 4,4'-bipyridine(1.0 mmol) into a stirred mixture of CH₃OH (7 mL) and H₂O (5 mL) containing Ni(NO₃)₂.6H₂O (1.0 mmol). The mixture was refluxed for 5 h and then allowed to cool to ambient temperature. The filtrate was evaporated slowly at room temperature for 3 days to yield yellow crystalline products.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular entities of the title compound, showing the atom-numbering scheme with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Intermolecular N—H···N hydrogen bonds.
	Fig. 3. Intermolecular N—H···N hydrogen bonds.

4,4'-Bipyridine–3,3'-disulfanediylbis(1H-1,2,4-triazole-5-amine) (1/1) top

Crystal data top

C₁₀H₈N₂·C₄H₆N₈S₂	Z = 2
M_r = 386.47	F(000) = 400
Triclinic, P1	D_x = 1.516 Mg m⁻³
a = 9.324 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4540 (11) Å	Cell parameters from 1617 reflections
c = 11.3840 (13) Å	θ = 2.4–26.4°
α = 109.560 (2)°	µ = 0.34 mm⁻¹
β = 104.089 (1)°	T = 298 K
γ = 105.627 (1)°	Block, yellow
V = 846.86 (17) Å³	0.35 × 0.30 × 0.21 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2952 independent reflections
Radiation source: fine-focus sealed tube	2121 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
phi and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→11
T_min = 0.891, T_max = 0.933	k = −6→11
4439 measured reflections	l = −13→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0426P)² + 0.3426P] where P = (F_o² + 2F_c²)/3
2952 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₀H₈N₂·C₄H₆N₈S₂	γ = 105.627 (1)°
M_r = 386.47	V = 846.86 (17) Å³
Triclinic, P1	Z = 2
a = 9.324 (1) Å	Mo Kα radiation
b = 9.4540 (11) Å	µ = 0.34 mm⁻¹
c = 11.3840 (13) Å	T = 298 K
α = 109.560 (2)°	0.35 × 0.30 × 0.21 mm
β = 104.089 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2952 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2121 reflections with I > 2σ(I)
T_min = 0.891, T_max = 0.933	R_int = 0.019
4439 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	Δρ_max = 0.26 e Å⁻³
2952 reflections	Δρ_min = −0.26 e Å⁻³
235 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
N1	0.6415 (3)	0.6418 (2)	0.1281 (2)	0.0365 (5)
N2	0.4984 (3)	0.6630 (3)	0.1020 (2)	0.0367 (5)
H2	0.4095	0.5917	0.0394	0.044*
N3	0.6698 (3)	0.8909 (2)	0.2725 (2)	0.0368 (5)
N4	0.3976 (3)	0.8634 (3)	0.1817 (2)	0.0499 (7)
H4A	0.3040	0.8023	0.1210	0.060*
H4B	0.4143	0.9587	0.2385	0.060*
N5	0.8542 (3)	0.3413 (3)	0.1018 (2)	0.0411 (6)
N6	0.8400 (3)	0.2361 (3)	0.1625 (2)	0.0398 (6)
H6	0.7998	0.1318	0.1206	0.048*
N7	0.9544 (2)	0.4807 (2)	0.3285 (2)	0.0346 (5)
N8	0.9016 (3)	0.2543 (3)	0.3827 (2)	0.0505 (7)
H8A	0.8650	0.1503	0.3539	0.061*
H8B	0.9406	0.3155	0.4674	0.061*
N9	0.2801 (3)	0.0985 (3)	0.0248 (2)	0.0488 (6)
N10	0.5992 (3)	0.8714 (3)	0.5836 (2)	0.0518 (7)
S1	0.94031 (9)	0.82733 (9)	0.31441 (8)	0.0479 (2)
S2	0.98658 (9)	0.65858 (9)	0.17888 (8)	0.0474 (2)
C1	0.5172 (3)	0.8101 (3)	0.1876 (3)	0.0342 (6)
C2	0.7366 (3)	0.7806 (3)	0.2306 (3)	0.0345 (6)
C3	0.8980 (3)	0.3206 (3)	0.2961 (3)	0.0349 (6)
C4	0.9235 (3)	0.4833 (3)	0.2058 (3)	0.0338 (6)
C5	0.4333 (4)	0.1698 (4)	0.1025 (3)	0.0540 (8)
H5	0.4996	0.1149	0.0828	0.065*
C6	0.5013 (3)	0.3195 (3)	0.2107 (3)	0.0478 (8)
H6A	0.6104	0.3626	0.2611	0.057*
C7	0.4085 (3)	0.4057 (3)	0.2443 (3)	0.0328 (6)
C8	0.2490 (4)	0.3329 (3)	0.1624 (3)	0.0526 (8)
H8	0.1800	0.3855	0.1789	0.063*
C9	0.1915 (4)	0.1821 (4)	0.0559 (3)	0.0565 (9)
H9	0.0832	0.1364	0.0027	0.068*
C10	0.6900 (4)	0.7885 (3)	0.5540 (3)	0.0473 (7)
H10	0.7973	0.8336	0.6097	0.057*
C11	0.6350 (3)	0.6395 (3)	0.4456 (3)	0.0391 (7)
H11	0.7049	0.5881	0.4293	0.047*
C12	0.4754 (3)	0.5667 (3)	0.3612 (3)	0.0326 (6)
C13	0.3814 (4)	0.6530 (3)	0.3920 (3)	0.0490 (8)
H13	0.2735	0.6108	0.3388	0.059*
C14	0.4475 (4)	0.8020 (4)	0.5018 (3)	0.0565 (9)
H14	0.3808	0.8573	0.5195	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0370 (13)	0.0262 (12)	0.0393 (13)	0.0107 (10)	0.0112 (11)	0.0092 (10)
N2	0.0333 (13)	0.0298 (12)	0.0337 (12)	0.0087 (10)	0.0081 (10)	0.0041 (10)
N3	0.0449 (14)	0.0256 (11)	0.0312 (12)	0.0104 (10)	0.0089 (11)	0.0083 (10)
N4	0.0478 (15)	0.0401 (14)	0.0402 (14)	0.0223 (12)	0.0023 (12)	−0.0016 (11)
N5	0.0422 (14)	0.0398 (14)	0.0339 (13)	0.0141 (11)	0.0088 (11)	0.0123 (11)
N6	0.0417 (14)	0.0273 (12)	0.0344 (13)	0.0096 (10)	0.0073 (11)	0.0026 (10)
N7	0.0365 (13)	0.0254 (11)	0.0327 (12)	0.0096 (10)	0.0070 (10)	0.0078 (10)
N8	0.0713 (18)	0.0257 (12)	0.0387 (14)	0.0086 (12)	0.0105 (13)	0.0103 (11)
N9	0.0640 (18)	0.0304 (13)	0.0403 (14)	0.0096 (13)	0.0162 (13)	0.0104 (11)
N10	0.0624 (18)	0.0364 (14)	0.0462 (15)	0.0167 (13)	0.0216 (14)	0.0067 (12)
S1	0.0404 (4)	0.0315 (4)	0.0540 (5)	0.0084 (3)	0.0038 (4)	0.0120 (3)
S2	0.0447 (5)	0.0507 (5)	0.0620 (5)	0.0224 (4)	0.0264 (4)	0.0334 (4)
C1	0.0440 (17)	0.0257 (14)	0.0290 (14)	0.0112 (12)	0.0123 (13)	0.0099 (12)
C2	0.0381 (16)	0.0252 (14)	0.0362 (15)	0.0086 (12)	0.0109 (13)	0.0133 (12)
C3	0.0321 (15)	0.0282 (14)	0.0351 (15)	0.0093 (12)	0.0081 (12)	0.0078 (12)
C4	0.0274 (14)	0.0332 (15)	0.0368 (15)	0.0130 (12)	0.0082 (12)	0.0121 (13)
C5	0.056 (2)	0.0391 (17)	0.060 (2)	0.0200 (16)	0.0279 (18)	0.0077 (15)
C6	0.0368 (17)	0.0380 (16)	0.0511 (18)	0.0121 (13)	0.0125 (14)	0.0036 (14)
C7	0.0347 (15)	0.0286 (14)	0.0354 (15)	0.0093 (12)	0.0134 (12)	0.0158 (12)
C8	0.0428 (18)	0.0387 (17)	0.057 (2)	0.0166 (14)	0.0068 (15)	0.0065 (15)
C9	0.0483 (19)	0.0402 (18)	0.055 (2)	0.0074 (15)	0.0001 (16)	0.0121 (16)
C10	0.0466 (18)	0.0402 (17)	0.0425 (17)	0.0099 (14)	0.0116 (15)	0.0120 (14)
C11	0.0386 (16)	0.0334 (15)	0.0423 (16)	0.0137 (13)	0.0150 (13)	0.0129 (13)
C12	0.0360 (15)	0.0265 (13)	0.0347 (14)	0.0105 (12)	0.0133 (12)	0.0135 (12)
C13	0.0392 (17)	0.0426 (17)	0.0503 (18)	0.0173 (14)	0.0116 (14)	0.0052 (14)
C14	0.062 (2)	0.0481 (19)	0.057 (2)	0.0318 (17)	0.0263 (18)	0.0082 (16)

Geometric parameters (Å, º) top

N1—C2	1.309 (3)	N10—C10	1.328 (4)
N1—N2	1.378 (3)	S1—C2	1.760 (3)
N2—C1	1.339 (3)	S1—S2	2.0392 (11)
N2—H2	0.8600	S2—C4	1.757 (3)
N3—C1	1.339 (3)	C5—C6	1.375 (4)
N3—C2	1.366 (3)	C5—H5	0.9300
N4—C1	1.338 (3)	C6—C7	1.376 (4)
N4—H4A	0.8600	C6—H6A	0.9300
N4—H4B	0.8600	C7—C8	1.378 (4)
N5—C4	1.310 (3)	C7—C12	1.485 (3)
N5—N6	1.385 (3)	C8—C9	1.380 (4)
N6—C3	1.341 (3)	C8—H8	0.9300
N6—H6	0.8600	C9—H9	0.9300
N7—C3	1.343 (3)	C10—C11	1.382 (4)
N7—C4	1.366 (3)	C10—H10	0.9300
N8—C3	1.333 (3)	C11—C12	1.386 (4)
N8—H8A	0.8600	C11—H11	0.9300
N8—H8B	0.8600	C12—C13	1.378 (4)
N9—C9	1.319 (4)	C13—C14	1.380 (4)
N9—C5	1.321 (4)	C13—H13	0.9300
N10—C14	1.322 (4)	C14—H14	0.9300

C2—N1—N2	101.2 (2)	N7—C4—S2	125.08 (19)
C1—N2—N1	110.6 (2)	N9—C5—C6	124.5 (3)
C1—N2—H2	124.7	N9—C5—H5	117.8
N1—N2—H2	124.7	C6—C5—H5	117.8
C1—N3—C2	101.9 (2)	C5—C6—C7	120.1 (3)
C1—N4—H4A	120.0	C5—C6—H6A	119.9
C1—N4—H4B	120.0	C7—C6—H6A	119.9
H4A—N4—H4B	120.0	C6—C7—C8	115.7 (2)
C4—N5—N6	101.7 (2)	C6—C7—C12	122.3 (2)
C3—N6—N5	110.1 (2)	C8—C7—C12	122.0 (2)
C3—N6—H6	125.0	C7—C8—C9	120.1 (3)
N5—N6—H6	125.0	C7—C8—H8	120.0
C3—N7—C4	102.4 (2)	C9—C8—H8	120.0
C3—N8—H8A	120.0	N9—C9—C8	124.3 (3)
C3—N8—H8B	120.0	N9—C9—H9	117.9
H8A—N8—H8B	120.0	C8—C9—H9	117.9
C9—N9—C5	115.4 (2)	N10—C10—C11	124.1 (3)
C14—N10—C10	115.7 (2)	N10—C10—H10	118.0
C2—S1—S2	102.20 (9)	C11—C10—H10	118.0
C4—S2—S1	104.74 (9)	C10—C11—C12	119.9 (2)
N4—C1—N2	122.7 (2)	C10—C11—H11	120.1
N4—C1—N3	127.5 (2)	C12—C11—H11	120.1
N2—C1—N3	109.8 (2)	C13—C12—C11	115.9 (2)
N1—C2—N3	116.6 (2)	C13—C12—C7	121.6 (2)
N1—C2—S1	123.3 (2)	C11—C12—C7	122.4 (2)
N3—C2—S1	120.13 (19)	C12—C13—C14	120.1 (3)
N8—C3—N6	124.6 (2)	C12—C13—H13	120.0
N8—C3—N7	125.6 (2)	C14—C13—H13	120.0
N6—C3—N7	109.8 (2)	N10—C14—C13	124.3 (3)
N5—C4—N7	116.1 (2)	N10—C14—H14	117.8
N5—C4—S2	118.5 (2)	C13—C14—H14	117.8

C2—N1—N2—C1	0.6 (3)	S1—S2—C4—N7	−44.3 (2)
C4—N5—N6—C3	1.1 (3)	C9—N9—C5—C6	0.8 (5)
C2—S1—S2—C4	−83.57 (13)	N9—C5—C6—C7	0.1 (5)
N1—N2—C1—N4	178.1 (2)	C5—C6—C7—C8	−1.0 (4)
N1—N2—C1—N3	−0.1 (3)	C5—C6—C7—C12	179.1 (3)
C2—N3—C1—N4	−178.5 (3)	C6—C7—C8—C9	1.0 (4)
C2—N3—C1—N2	−0.4 (3)	C12—C7—C8—C9	−179.1 (3)
N2—N1—C2—N3	−0.9 (3)	C5—N9—C9—C8	−0.8 (5)
N2—N1—C2—S1	178.47 (19)	C7—C8—C9—N9	0.0 (5)
C1—N3—C2—N1	0.8 (3)	C14—N10—C10—C11	0.3 (5)
C1—N3—C2—S1	−178.55 (19)	N10—C10—C11—C12	−1.0 (5)
S2—S1—C2—N1	17.6 (2)	C10—C11—C12—C13	1.0 (4)
S2—S1—C2—N3	−163.10 (19)	C10—C11—C12—C7	−179.1 (3)
N5—N6—C3—N8	−179.9 (3)	C6—C7—C12—C13	178.7 (3)
N5—N6—C3—N7	−1.2 (3)	C8—C7—C12—C13	−1.3 (4)
C4—N7—C3—N8	179.5 (3)	C6—C7—C12—C11	−1.3 (4)
C4—N7—C3—N6	0.8 (3)	C8—C7—C12—C11	178.8 (3)
N6—N5—C4—N7	−0.6 (3)	C11—C12—C13—C14	−0.4 (4)
N6—N5—C4—S2	173.25 (17)	C7—C12—C13—C14	179.7 (3)
C3—N7—C4—N5	−0.1 (3)	C10—N10—C14—C13	0.4 (5)
C3—N7—C4—S2	−173.50 (19)	C12—C13—C14—N10	−0.3 (5)
S1—S2—C4—N5	142.40 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1ⁱ	0.86	2.22	2.850 (3)	131
N4—H4A···N5ⁱ	0.86	2.29	3.058 (3)	149
N4—H4B···N10ⁱⁱ	0.86	2.18	2.977 (3)	154
N6—H6···N9ⁱⁱⁱ	0.86	2.04	2.867 (3)	162
N8—H8A···N3^iv	0.86	2.33	3.137 (3)	156
N8—H8B···N7^v	0.86	2.22	3.068 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂·C₄H₆N₈S₂
M_r	386.47
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.324 (1), 9.4540 (11), 11.3840 (13)
α, β, γ (°)	109.560 (2), 104.089 (1), 105.627 (1)
V (Å³)	846.86 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.35 × 0.30 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.891, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	4439, 2952, 2121
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.106, 1.04
No. of reflections	2952
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1ⁱ	0.86	2.22	2.850 (3)	130.5
N4—H4A···N5ⁱ	0.86	2.29	3.058 (3)	148.7
N4—H4B···N10ⁱⁱ	0.86	2.18	2.977 (3)	154.0
N6—H6···N9ⁱⁱⁱ	0.86	2.04	2.867 (3)	162.1
N8—H8A···N3^iv	0.86	2.33	3.137 (3)	156.0
N8—H8B···N7^v	0.86	2.22	3.068 (3)	166.8

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No.21171119), the National High Technology Research and Development Program 863 of China (2012 A A063201), the Beijing Personnel Bureau, the National Keystone Basic Research Program (973 Program) under grant Nos. 2007CB310408 and 2006CB302901), the Committee of Education of the Beijing Foundation of China (grant No. KM201210028020).

References

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