N-p-Tolyl-1,3-selenazolo[5,4-b]pyridin-2-amine.

In the title compound, C13H11N3Se, the dihedral angle between the mean plane of the fused seleno-azolo-pyridine ring system and the p-toluidine ring is 14.260 (5)°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, forming zigzag chains extending along the b-axis direction.

Related literature

For the bioactivity of organoselenium, see: Garud et al. (2007 ▶); Ling et al. (2010 ▶); Plamen et al. (2010 ▶). For crystallographic studies on selenazolo derivatives, see: Plamen et al. (2004 ▶).

Experimental

Crystal data

C13H11N3Se

M = 288.21

Orthorhombic,

a = 13.138 (2) Å

b = 10.0323 (19) Å

c = 17.838 (3) Å

V = 2351.2 (7) Å3

Z = 8

Cu Kα radiation

μ = 4.15 mm−1

T = 153 K

0.30 × 0.30 × 0.20 mm

Data collection

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.369, T max = 0.491

5248 measured reflections

1863 independent reflections

1423 reflections with I > 2σI)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.094

wR(F 2) = 0.314

S = 1.28

1863 reflections

155 parameters

H-atom parameters constrained

Δρmax = 1.47 e Å−3

Δρmin = −2.49 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813023659/zs2275sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023659/zs2275Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023659/zs2275Isup3.cml

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

C13H11N3Se	F(000) = 1152
Mr = 288.21	Dx = 1.628 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7867 reflections
a = 13.138 (2) Å	θ = 1.3–61.9°
b = 10.0323 (19) Å	µ = 4.15 mm−1
c = 17.838 (3) Å	T = 153 K
V = 2351.2 (7) Å3	Prism, yellow
Z = 8	0.30 × 0.30 × 0.20 mm

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer	1863 independent reflections
Radiation source: fine-focus sealed tube	1423 reflections with I > 2s˘I)
Graphite monochromator	Rint = 0.064
Detector resolution: 16.0288 pixels mm-1	θmax = 63.6°, θmin = 6.0°
ω scans	h = −15→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.369, Tmax = 0.491	l = −13→20
5248 measured reflections

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)] = 0.094	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.314	H-atom parameters constrained
S = 1.28	w = 1/[σ2(Fo2) + (0.0796P)2 + 53.5115P] where P = (Fo2 + 2Fc2)/3
1863 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 1.47 e Å−3
0 restraints	Δρmin = −2.49 e Å−3

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.

	x	y	z	Uiso*/Ueq
C2	0.1440 (11)	0.5123 (17)	0.1134 (9)	0.058 (4)
H2	0.1245	0.5846	0.0821	0.069*
C3	0.2452 (11)	0.4817 (14)	0.1192 (8)	0.049 (3)
H3	0.2937	0.5321	0.0917	0.058*
C4	0.2779 (10)	0.3779 (13)	0.1647 (7)	0.042 (3)
H4	0.3483	0.3586	0.1694	0.050*
C6	0.1034 (9)	0.3460 (16)	0.1916 (7)	0.045 (3)
C5	0.2051 (9)	0.3016 (13)	0.2038 (7)	0.035 (3)
C8	0.1441 (10)	0.1537 (15)	0.2778 (7)	0.041 (3)
C11	0.2188 (10)	−0.0164 (13)	0.3649 (7)	0.038 (3)
C16	0.3195 (10)	0.0139 (14)	0.3591 (8)	0.045 (3)
H16	0.3399	0.0836	0.3263	0.054*
C15	0.3925 (11)	−0.0535 (18)	0.3993 (8)	0.059 (4)
H15	0.4618	−0.0279	0.3942	0.071*
C14	0.3684 (12)	−0.1555 (19)	0.4460 (8)	0.058 (4)
C13	0.2672 (13)	−0.189 (2)	0.4510 (8)	0.064 (5)
H13	0.2482	−0.2601	0.4834	0.077*
C12	0.1923 (12)	−0.1245 (16)	0.4116 (7)	0.052 (4)
H12	0.1234	−0.1523	0.4156	0.063*
C17	0.4499 (16)	−0.2322 (19)	0.4884 (9)	0.074 (5)
H17A	0.4471	−0.3265	0.4742	0.110*
H17B	0.4380	−0.2236	0.5425	0.110*
H17C	0.5170	−0.1960	0.4760	0.110*
N1	0.0717 (9)	0.4456 (15)	0.1496 (7)	0.058 (4)
N9	0.2255 (8)	0.1982 (14)	0.2518 (6)	0.049 (3)
N10	0.1388 (8)	0.0493 (14)	0.3276 (7)	0.054 (3)
H10	0.0772	0.0197	0.3375	0.065*
Se7	0.01740 (10)	0.22670 (19)	0.24564 (9)	0.0504 (7)

	U11	U22	U33	U12	U13	U23
C2	0.048 (8)	0.060 (10)	0.066 (10)	0.007 (8)	−0.001 (7)	−0.012 (8)
C3	0.053 (8)	0.028 (7)	0.065 (9)	0.000 (6)	0.001 (7)	0.010 (7)
C4	0.038 (7)	0.035 (8)	0.052 (8)	0.001 (6)	0.000 (6)	0.015 (6)
C6	0.028 (6)	0.066 (10)	0.041 (7)	−0.006 (7)	−0.001 (5)	−0.006 (7)
C5	0.031 (6)	0.032 (7)	0.043 (7)	−0.006 (5)	0.001 (5)	−0.007 (6)
C8	0.036 (7)	0.048 (8)	0.040 (7)	0.016 (6)	0.002 (6)	−0.005 (6)
C11	0.051 (8)	0.032 (7)	0.031 (6)	0.006 (6)	0.005 (5)	−0.003 (6)
C16	0.040 (7)	0.042 (8)	0.052 (8)	0.004 (6)	0.005 (6)	0.017 (7)
C15	0.039 (7)	0.082 (13)	0.056 (9)	0.003 (8)	0.004 (7)	0.004 (9)
C14	0.060 (9)	0.078 (12)	0.036 (7)	0.013 (8)	0.001 (6)	0.007 (8)
C13	0.067 (11)	0.084 (14)	0.041 (8)	−0.006 (9)	0.005 (7)	0.017 (9)
C12	0.055 (9)	0.059 (10)	0.043 (7)	−0.005 (8)	0.004 (7)	−0.006 (7)
C17	0.094 (14)	0.066 (12)	0.061 (10)	0.011 (10)	−0.010 (9)	0.007 (9)
N1	0.036 (6)	0.089 (11)	0.048 (7)	0.018 (7)	−0.007 (5)	0.000 (7)
N9	0.024 (6)	0.082 (10)	0.042 (6)	0.005 (5)	0.002 (4)	0.012 (6)
N10	0.025 (5)	0.082 (10)	0.054 (7)	−0.001 (6)	0.001 (5)	−0.009 (7)
Se7	0.0237 (9)	0.0734 (13)	0.0542 (10)	−0.0005 (7)	−0.0003 (6)	−0.0021 (8)

C2—N1	1.33 (2)	C11—N10	1.408 (17)
C2—C3	1.37 (2)	C11—C12	1.41 (2)
C2—H2	0.9500	C16—C15	1.38 (2)
C3—C4	1.388 (18)	C16—H16	0.9500
C3—H3	0.9500	C15—C14	1.36 (2)
C4—C5	1.410 (17)	C15—H15	0.9500
C4—H4	0.9500	C14—C13	1.37 (2)
C6—N1	1.316 (19)	C14—C17	1.52 (2)
C6—C5	1.425 (18)	C13—C12	1.37 (2)
C6—Se7	1.907 (14)	C13—H13	0.9500
C5—N9	1.371 (17)	C12—H12	0.9500
C8—N9	1.248 (17)	C17—H17A	0.9800
C8—N10	1.375 (18)	C17—H17B	0.9800
C8—Se7	1.907 (12)	C17—H17C	0.9800
C11—C16	1.362 (19)	N10—H10	0.8800
N1—C2—C3	123.0 (16)	C14—C15—C16	121.9 (14)
N1—C2—H2	118.5	C14—C15—H15	119.1
C3—C2—H2	118.5	C16—C15—H15	119.1
C2—C3—C4	120.8 (14)	C15—C14—C13	116.8 (15)
C2—C3—H3	119.6	C15—C14—C17	121.6 (15)
C4—C3—H3	119.6	C13—C14—C17	121.6 (16)
C3—C4—C5	119.2 (12)	C12—C13—C14	123.0 (16)
C3—C4—H4	120.4	C12—C13—H13	118.5
C5—C4—H4	120.4	C14—C13—H13	118.5
N1—C6—C5	128.4 (12)	C13—C12—C11	119.3 (14)
N1—C6—Se7	125.2 (10)	C13—C12—H12	120.4
C5—C6—Se7	106.4 (10)	C11—C12—H12	120.4
N9—C5—C4	126.0 (11)	C14—C17—H17A	109.5
N9—C5—C6	121.0 (11)	C14—C17—H17B	109.5
C4—C5—C6	113.0 (12)	H17A—C17—H17B	109.5
N9—C8—N10	123.7 (12)	C14—C17—H17C	109.5
N9—C8—Se7	119.9 (11)	H17A—C17—H17C	109.5
N10—C8—Se7	116.3 (9)	H17B—C17—H17C	109.5
C16—C11—N10	125.7 (12)	C6—N1—C2	115.7 (12)
C16—C11—C12	117.2 (13)	C8—N9—C5	109.6 (11)
N10—C11—C12	117.1 (12)	C8—N10—C11	128.7 (11)
C11—C16—C15	121.8 (13)	C8—N10—H10	115.7
C11—C16—H16	119.1	C11—N10—H10	115.7
C15—C16—H16	119.1	C8—Se7—C6	82.9 (6)
N1—C2—C3—C4	−1 (2)	N10—C11—C12—C13	−177.9 (13)
C2—C3—C4—C5	2 (2)	C5—C6—N1—C2	1 (2)
C3—C4—C5—N9	−178.7 (13)	Se7—C6—N1—C2	−176.5 (11)
C3—C4—C5—C6	−1.3 (18)	C3—C2—N1—C6	−1 (2)
N1—C6—C5—N9	177.7 (14)	N10—C8—N9—C5	179.9 (12)
Se7—C6—C5—N9	−4.7 (15)	Se7—C8—N9—C5	2.3 (17)
N1—C6—C5—C4	0 (2)	C4—C5—N9—C8	179.0 (13)
Se7—C6—C5—C4	177.8 (9)	C6—C5—N9—C8	1.8 (18)
N10—C11—C16—C15	178.2 (14)	N9—C8—N10—C11	8 (2)
C12—C11—C16—C15	−3 (2)	Se7—C8—N10—C11	−174.5 (11)
C11—C16—C15—C14	1 (2)	C16—C11—N10—C8	1 (2)
C16—C15—C14—C13	0 (2)	C12—C11—N10—C8	−177.8 (13)
C16—C15—C14—C17	178.1 (15)	N9—C8—Se7—C6	−4.1 (12)
C15—C14—C13—C12	0 (3)	N10—C8—Se7—C6	178.1 (11)
C17—C14—C13—C12	−177.8 (15)	N1—C6—Se7—C8	−178.1 (13)
C14—C13—C12—C11	−2 (3)	C5—C6—Se7—C8	4.2 (9)
C16—C11—C12—C13	3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···N1i	0.88	2.11	2.983 (16)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯N1i	0.88	2.11	2.983 (16)	175

Symmetry code: (i) .