2-[(2,6-Dichloro­benz­yl)amino]-N-(4-methyl­thia­zol-2-yl)acetamide

Luo, J.; Zhao, G.-L.; Shao, H.; Wang, Y.-L.; Qu, B.-H.

doi:10.1107/S1600536810003089

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o518

doi:10.1107/S1600536810003089

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2-[(2,6-Dichlorobenzyl)amino]-N-(4-methylthiazol-2-yl)acetamide

Jie Luo,^a Gui-Long Zhao,^b Hua Shao,^b Yu-Li Wang ^a and Bao-Han Qu ^a ^*

^aCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, People's Republic of China, and ^bTianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
^*Correspondence e-mail: qubaohan2009@yahoo.cn

(Received 27 December 2009; accepted 25 January 2010; online 3 February 2010)

In the title compound, C₁₃H₁₃Cl₂N₃OS, the thiazole and benzene rings are roughly parallel to one another in two layers [dihedral angle = 5.08 (2)°] because the N—C—C—N—C chain that links the two rings is folded [N—C—C—N torsion angle = 12.0 (2)°] rather than fully extended. An intramolecular N—H⋯N interaction occurs. In the crystal, weak intermolecular N—H⋯N and C—H⋯O interactions are present and π–π interactions are indicated by the short distances [3.507 (3)–3.665 (2) Å] between the centroids of the thiazole and benzene rings.

Related literature

For details of the biological activity of Dipeptidyl peptidase IV (DPP-IV) inhibitors, see: Cheon et al. (2005 ); Kondo et al. (2007 ); Sakashita et al. (2006 ); Zhan et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₃Cl₂N₃OS
M_r = 330.22
Monoclinic, C 2/c
a = 14.008 (4) Å
b = 18.133 (5) Å
c = 11.390 (3) Å
β = 97.341 (3)°
V = 2869.4 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 113 K
0.22 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.880, T_max = 0.911
11103 measured reflections
3371 independent reflections
3150 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.131
S = 1.20
3371 reflections
191 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1ⁱ	0.89 (2)	2.32 (2)	3.130 (2)	150.9 (17)
C7—H7B⋯O1ⁱⁱ	0.99	2.53	3.3233 (19)	137
N2—H2⋯N3	0.84 (2)	2.26 (2)	2.6742 (19)	111 (2)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536810003089/fl2286sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003089/fl2286Isup2.hkl

checkCIF report

Comment top

Dipeptidyl peptidase IV (DPP-IV) inhibitors are a new class of antidiabetic agents (Cheon et al., 2005; Kondo et al., 2007; Sakashita et al., 2006) and the title compound was prepared as a novel DPP-IV inhibitor (Zhan et al., 2009). We reported the crystal structure here.

In title compound, all bond lengths in the molecular are normal (Allen et al., 1987). Atoms C4—C6/N2/N3/O1 lie in thiazole (C1—C3/N1/S1) plane with maximun least squares plane deviation for C4 0.065 (2) Å. Thiazole ring (C1—C3/N1/S1) and benzene ring (C8—C13) are essentially parallel to one another (dihedral angle of 5.08 (2) °) because the N—C—C—N—C chain that links the two rings is folded ((N—C—C—N torsion angle of 12.0 (2) °) rather than fully extended. π—π interactions are indicated by the short distance (Cg1···Cg1 distance of 3.665 (2) Å, symmetry code: 1-x,y,1/2-z; Cg1···Cg2 distance of 3.766 (3) Å, symmetry code: 1/2-x,1/2-y,-z; Cg1···Cg2 distance of 3.507 (3) Å, symmetry code: 1-x,y,-1/2-z) between the centroids of the thiazole rings C1—C3/N1/S1 (Cg1) and benzene rings C8—C13 (Cg2) (Table 1). There are intramolecular interaction and weaker N—H···N, C—H···O intermolecular interactions, which stabilized the structure (Table 1).

Related literature top

For details of the biological activity of Dipeptidyl peptidase IV (DPP-IV) inhibitors, see: Cheon et al. (2005); Kondo et al. (2007); Sakashita et al. (2006); Zhan et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

A round-bottomed flask was charged with [(2,6-dichlorophenyl)methyl]amine (1.76 g, 10 mmol), 2-[(2-chloroacetyl)amino]-4-methylthiazole (1.91 g, 10 mmol), triethylamine (1.21 g, 12 mmol) and THF (20 ml), and the resulting mixture was stirred at room temperature over night. The reaction mixture was concentrated on a rotary evaporator and diluted with 100 ml of dichloromethane, and the organic solution thus obtained was washed with saturated brine, dried over sodium sulfate and evaporated on a rotary evaporator to afford a solid residue, which was triturated with a mixed solvent consisting of 5 ml of dichloromethane and 10 ml of ethyl acetate and filtered. The crystals were collected and dried to yield the title compound as colorless crystals 2.51 g (Yield 76.1%). Crystals suitable for single-crystal X-ray diffraction were obtained via slow evaporation at room temperature of a solution of the pure title compound in dichloromethane.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 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 structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram of the molecule of the title compound, view down b axis. Hydrogen bonds are shown as dashed lines.

2-[(2,6-Dichlorobenzyl)amino]-N-(4-methylthiazol-2-yl)acetamide top

Crystal data top

C₁₃H₁₃Cl₂N₃OS	F(000) = 1360
M_r = 330.22	D_x = 1.529 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 5153 reflections
a = 14.008 (4) Å	θ = 1.8–27.9°
b = 18.133 (5) Å	µ = 0.60 mm⁻¹
c = 11.390 (3) Å	T = 113 K
β = 97.341 (3)°	Prism, colorless
V = 2869.4 (14) Å³	0.22 × 0.18 × 0.16 mm
Z = 8

Data collection top

Rigaku Saturn diffractometer	3371 independent reflections
Radiation source: rotating anode	3150 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.036
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 1.9°
ω and ϕ scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −23→18
T_min = 0.880, T_max = 0.911	l = −13→14
11103 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0837P)² + 0.6909P] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max < 0.001
3371 reflections	Δρ_max = 0.65 e Å⁻³
191 parameters	Δρ_min = −0.83 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.086 (3)

Crystal data top

C₁₃H₁₃Cl₂N₃OS	V = 2869.4 (14) Å³
M_r = 330.22	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 14.008 (4) Å	µ = 0.60 mm⁻¹
b = 18.133 (5) Å	T = 113 K
c = 11.390 (3) Å	0.22 × 0.18 × 0.16 mm
β = 97.341 (3)°

Data collection top

Rigaku Saturn diffractometer	3371 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3150 reflections with I > 2σ(I)
T_min = 0.880, T_max = 0.911	R_int = 0.036
11103 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	Δρ_max = 0.65 e Å⁻³
3371 reflections	Δρ_min = −0.83 e Å⁻³
191 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
Cl1	0.59889 (3)	0.30694 (2)	0.64087 (4)	0.03507 (18)
Cl2	0.60026 (3)	0.00844 (2)	0.65202 (3)	0.03000 (17)
S1	0.60179 (3)	0.37651 (2)	0.15270 (3)	0.02879 (17)
O1	0.59946 (9)	0.22476 (8)	0.16770 (10)	0.0371 (3)
N2	0.65223 (10)	0.28348 (8)	0.33975 (11)	0.0262 (3)
N1	0.66017 (10)	0.41118 (7)	0.37000 (11)	0.0260 (3)
N3	0.66669 (9)	0.15932 (7)	0.46748 (11)	0.0244 (3)
C1	0.64101 (10)	0.35505 (9)	0.29875 (12)	0.0242 (3)
C2	0.64316 (12)	0.47666 (9)	0.30816 (14)	0.0284 (3)
C3	0.61282 (13)	0.46827 (10)	0.19104 (15)	0.0325 (4)
H3A	0.5994	0.5080	0.1370	0.039*
C4	0.65614 (15)	0.54732 (10)	0.37486 (15)	0.0368 (4)
H4A	0.6702	0.5869	0.3211	0.055*
H4B	0.7097	0.5425	0.4387	0.055*
H4C	0.5971	0.5590	0.4087	0.055*
C5	0.63006 (11)	0.22221 (9)	0.27318 (13)	0.0282 (4)
C6	0.64796 (12)	0.15012 (9)	0.33971 (13)	0.0290 (4)
H6A	0.5911	0.1178	0.3207	0.035*
H6B	0.7037	0.1250	0.3119	0.035*
C7	0.57765 (11)	0.15610 (8)	0.52297 (13)	0.0239 (3)
H7A	0.5421	0.1103	0.4986	0.029*
H7B	0.5360	0.1986	0.4964	0.029*
C8	0.60135 (10)	0.15779 (8)	0.65549 (12)	0.0216 (3)
C9	0.61402 (11)	0.22376 (8)	0.71857 (13)	0.0251 (3)
C10	0.63758 (11)	0.22652 (10)	0.84107 (14)	0.0299 (4)
H10	0.6454	0.2726	0.8809	0.036*
C11	0.64947 (12)	0.16110 (10)	0.90375 (14)	0.0299 (4)
H11	0.6655	0.1622	0.9873	0.036*
C12	0.63813 (11)	0.09389 (9)	0.84525 (14)	0.0275 (3)
H12	0.6462	0.0488	0.8880	0.033*
C13	0.61481 (10)	0.09381 (8)	0.72306 (13)	0.0232 (3)
H2	0.6752 (16)	0.2782 (14)	0.411 (2)	0.049 (6)*
H3	0.7065 (14)	0.1245 (11)	0.5004 (18)	0.030 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0473 (3)	0.0242 (2)	0.0324 (3)	−0.00894 (14)	−0.0001 (2)	0.00170 (13)
Cl2	0.0396 (3)	0.0237 (3)	0.0275 (3)	−0.00282 (13)	0.00714 (17)	0.00110 (12)
S1	0.0322 (3)	0.0420 (3)	0.0119 (2)	−0.00337 (14)	0.00174 (16)	0.00325 (13)
O1	0.0493 (8)	0.0486 (8)	0.0121 (5)	−0.0193 (5)	−0.0016 (5)	−0.0025 (5)
N2	0.0355 (7)	0.0315 (7)	0.0105 (6)	−0.0120 (5)	−0.0011 (5)	0.0016 (5)
N1	0.0302 (7)	0.0323 (7)	0.0157 (6)	−0.0046 (5)	0.0031 (5)	0.0022 (5)
N3	0.0305 (7)	0.0278 (7)	0.0147 (6)	−0.0082 (5)	0.0028 (5)	−0.0007 (4)
C1	0.0244 (7)	0.0353 (8)	0.0131 (7)	−0.0071 (6)	0.0029 (5)	0.0024 (5)
C2	0.0309 (8)	0.0345 (8)	0.0211 (8)	0.0034 (6)	0.0079 (6)	0.0043 (6)
C3	0.0397 (9)	0.0384 (9)	0.0200 (8)	0.0065 (7)	0.0066 (6)	0.0064 (6)
C4	0.0546 (11)	0.0321 (8)	0.0253 (8)	0.0080 (7)	0.0110 (7)	0.0037 (6)
C5	0.0331 (8)	0.0380 (8)	0.0134 (7)	−0.0158 (6)	0.0027 (6)	−0.0025 (6)
C6	0.0411 (9)	0.0298 (8)	0.0161 (8)	−0.0137 (6)	0.0033 (6)	−0.0048 (6)
C7	0.0282 (7)	0.0285 (8)	0.0146 (7)	−0.0088 (5)	0.0007 (5)	0.0015 (5)
C8	0.0222 (7)	0.0265 (8)	0.0160 (7)	−0.0061 (5)	0.0016 (5)	0.0002 (5)
C9	0.0271 (7)	0.0277 (7)	0.0201 (7)	−0.0056 (5)	0.0008 (6)	0.0005 (5)
C10	0.0297 (8)	0.0367 (8)	0.0226 (8)	−0.0045 (6)	0.0007 (6)	−0.0084 (6)
C11	0.0273 (8)	0.0471 (10)	0.0147 (7)	−0.0007 (6)	0.0007 (6)	−0.0007 (6)
C12	0.0262 (7)	0.0378 (9)	0.0190 (7)	0.0009 (6)	0.0042 (6)	0.0064 (6)
C13	0.0236 (7)	0.0272 (7)	0.0192 (7)	−0.0035 (5)	0.0044 (5)	0.0009 (5)

Geometric parameters (Å, º) top

Cl1—C9	1.7480 (16)	C4—H4B	0.9800
Cl2—C13	1.7465 (16)	C4—H4C	0.9800
S1—C3	1.7222 (19)	C5—C6	1.516 (2)
S1—C1	1.7282 (15)	C6—H6A	0.9900
O1—C5	1.2238 (19)	C6—H6B	0.9900
N2—C5	1.359 (2)	C7—C8	1.5038 (19)
N2—C1	1.381 (2)	C7—H7A	0.9900
N2—H2	0.84 (2)	C7—H7B	0.9900
N1—C1	1.308 (2)	C8—C13	1.392 (2)
N1—C2	1.385 (2)	C8—C9	1.395 (2)
N3—C6	1.4550 (19)	C9—C10	1.393 (2)
N3—C7	1.470 (2)	C10—C11	1.384 (3)
N3—H3	0.89 (2)	C10—H10	0.9500
C2—C3	1.356 (2)	C11—C12	1.388 (2)
C2—C4	1.489 (3)	C11—H11	0.9500
C3—H3A	0.9500	C12—C13	1.388 (2)
C4—H4A	0.9800	C12—H12	0.9500

C3—S1—C1	88.07 (8)	C5—C6—H6A	108.9
C5—N2—C1	124.86 (13)	N3—C6—H6B	108.9
C5—N2—H2	118.5 (17)	C5—C6—H6B	108.9
C1—N2—H2	116.6 (17)	H6A—C6—H6B	107.7
C1—N1—C2	110.07 (13)	N3—C7—C8	109.89 (11)
C6—N3—C7	111.78 (12)	N3—C7—H7A	109.7
C6—N3—H3	111.3 (13)	C8—C7—H7A	109.7
C7—N3—H3	108.1 (13)	N3—C7—H7B	109.7
N1—C1—N2	121.05 (13)	C8—C7—H7B	109.7
N1—C1—S1	115.90 (12)	H7A—C7—H7B	108.2
N2—C1—S1	123.05 (11)	C13—C8—C9	115.51 (13)
C3—C2—N1	114.58 (15)	C13—C8—C7	122.35 (13)
C3—C2—C4	126.94 (15)	C9—C8—C7	122.11 (13)
N1—C2—C4	118.44 (14)	C10—C9—C8	123.02 (14)
C2—C3—S1	111.37 (12)	C10—C9—Cl1	118.29 (12)
C2—C3—H3A	124.3	C8—C9—Cl1	118.69 (11)
S1—C3—H3A	124.3	C11—C10—C9	118.91 (15)
C2—C4—H4A	109.5	C11—C10—H10	120.5
C2—C4—H4B	109.5	C9—C10—H10	120.5
H4A—C4—H4B	109.5	C10—C11—C12	120.41 (15)
C2—C4—H4C	109.5	C10—C11—H11	119.8
H4A—C4—H4C	109.5	C12—C11—H11	119.8
H4B—C4—H4C	109.5	C11—C12—C13	118.67 (14)
O1—C5—N2	122.92 (15)	C11—C12—H12	120.7
O1—C5—C6	122.55 (14)	C13—C12—H12	120.7
N2—C5—C6	114.51 (13)	C12—C13—C8	123.46 (14)
N3—C6—C5	113.47 (13)	C12—C13—Cl2	117.64 (12)
N3—C6—H6A	108.9	C8—C13—Cl2	118.89 (11)

C2—N1—C1—N2	−179.90 (14)	N3—C7—C8—C13	−91.91 (15)
C2—N1—C1—S1	0.25 (17)	N3—C7—C8—C9	86.22 (17)
C5—N2—C1—N1	176.97 (15)	C13—C8—C9—C10	−0.6 (2)
C5—N2—C1—S1	−3.2 (2)	C7—C8—C9—C10	−178.88 (14)
C3—S1—C1—N1	0.33 (13)	C13—C8—C9—Cl1	179.82 (11)
C3—S1—C1—N2	−179.52 (14)	C7—C8—C9—Cl1	1.57 (19)
C1—N1—C2—C3	−0.9 (2)	C8—C9—C10—C11	0.3 (2)
C1—N1—C2—C4	177.06 (14)	Cl1—C9—C10—C11	179.80 (12)
N1—C2—C3—S1	1.16 (19)	C9—C10—C11—C12	0.1 (2)
C4—C2—C3—S1	−176.61 (15)	C10—C11—C12—C13	0.1 (2)
C1—S1—C3—C2	−0.81 (13)	C11—C12—C13—C8	−0.5 (2)
C1—N2—C5—O1	1.8 (3)	C11—C12—C13—Cl2	−179.61 (12)
C1—N2—C5—C6	−179.27 (14)	C9—C8—C13—C12	0.8 (2)
C7—N3—C6—C5	90.42 (15)	C7—C8—C13—C12	179.01 (14)
O1—C5—C6—N3	−169.05 (15)	C9—C8—C13—Cl2	179.86 (11)
N2—C5—C6—N3	12.0 (2)	C7—C8—C13—Cl2	−1.90 (19)
C6—N3—C7—C8	174.04 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1ⁱ	0.89 (2)	2.32 (2)	3.130 (2)	150.9 (17)
C7—H7B···O1ⁱⁱ	0.99	2.53	3.3233 (19)	137
N2—H2···N3	0.84 (2)	2.26 (2)	2.6742 (19)	111 (2)
Cg1···Cg1ⁱⁱ			3.665 (2)
Cg1···Cg2ⁱⁱⁱ			3.766 (3)
Cg2···Cg2^iv			3.507 (3)

Symmetry codes: (i) −x+3/2, −y+1/2, −z+1; (ii) −x+1, y, −z+1/2; (iii) −x+1/2, −y+1/2, −z; (iv) −x+1, y, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃Cl₂N₃OS
M_r	330.22
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	14.008 (4), 18.133 (5), 11.390 (3)
β (°)	97.341 (3)
V (Å³)	2869.4 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.880, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	11103, 3371, 3150
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.131, 1.20
No. of reflections	3371
No. of parameters	191
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.83

Computer programs: CrystalClear (Rigaku, 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
N3—H3···N1ⁱ	0.89 (2)	2.32 (2)	3.130 (2)	150.9 (17)
C7—H7B···O1ⁱⁱ	0.99	2.53	3.3233 (19)	136.7
N2—H2···N3	0.84 (2)	2.26 (2)	2.6742 (19)	111 (2)

Symmetry codes: (i) −x+3/2, −y+1/2, −z+1; (ii) −x+1, y, −z+1/2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Cheon, H. G., Kim, S.-S., Kim, K.-R., Rhee, S. D., Yang, S.-D., Ahn, J. H., Park, S.-D., Lee, J. M., Jung, W. H., Lee, H. S. & Kim, H. Y. (2005). Biochem. Pharmacol. 70, 22–29. Web of Science CrossRef PubMed CAS Google Scholar
Kondo, T., Sugimoto, I., Nekado, T., Ochi, K., Ohtani, T., Tajima, Y., Yamamoto, S., Kawabata, K., Nakai, H. & Toda, M. (2007). Bioorg. Med. Chem. 15, 2715–2735. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sakashita, H., Akahoshi, F., Kitajima, H., Tsutsumiuchi, R. & Hayashi, Y. (2006). Bioorg. Med. Chem. 14, 3662–3671. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhan, F. X., Wang, Y. L., Zhao, G. L., Xu, W. R., Li, Y. L., Zou, M. X., Tang, L. D. & Wang, J. W. (2009). Chin. J. Org. Chem. 29, 1236–1242 CAS Google Scholar

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Volume 66| Part 3| March 2010| Page o518

doi:10.1107/S1600536810003089

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