N-(2-Bromo-phen-yl)-1,3-selenazolo[5,4-b]pyridin-2-amine.

The mol-ecular structure of the title mol-ecule, C12H8BrN3Se, is built up from fused selenazolo and pyridine rings, linked to a 2-bromo-aniline group. In the crystal, pairs of mol-ecules are linked by N-H⋯N hydrogen bonds into dimers, forming eight-membered ring motifs.

Related literature

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

Experimental

Crystal data

C12H8BrN3Se

M = 353.08

Monoclinic,

a = 12.5312 (5) Å

b = 7.4562 (3) Å

c = 13.8913 (5) Å

β = 112.331 (4)°

V = 1200.60 (8) Å3

Z = 4

Cu Kα radiation

μ = 7.96 mm−1

T = 295 K

0.30 × 0.30 × 0.10 mm

Data collection

Agilent Xcalibur (Sapphire3, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) ▶ T min = 0.199, T max = 0.299

4420 measured reflections

1921 independent reflections

1779 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.132

S = 1.11

1921 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −1.88 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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813023969/fj2639sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023969/fj2639Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023969/fj2639Isup3.cml

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

C12H8BrN3Se	F(000) = 680
Mr = 353.08	Dx = 1.953 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 12.5312 (5) Å	Cell parameters from 1921 reflections
b = 7.4562 (3) Å	θ = 63.3–4.1°
c = 13.8913 (5) Å	µ = 7.96 mm−1
β = 112.331 (4)°	T = 295 K
V = 1200.60 (8) Å3	Prism, colorless
Z = 4	0.30 × 0.30 × 0.10 mm

Agilent Xcalibur (Sapphire3, Gemini ultra) diffractometer	1921 independent reflections
Radiation source: fine-focus sealed tube	1779 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.0288 pixels mm-1	θmax = 62.8°, θmin = 4.1°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −8→8
Tmin = 0.199, Tmax = 0.299	l = −16→14
4420 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
1921 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −1.88 e Å−3

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Se1	0.54412 (4)	0.09933 (7)	0.29605 (3)	0.0347 (2)
Br1	0.25269 (5)	−0.30042 (7)	0.03920 (4)	0.0499 (2)
C1	0.8930 (4)	0.1246 (6)	0.3969 (4)	0.0391 (10)
H1	0.9579	0.1449	0.4594	0.047*
N1	0.7879 (3)	0.1260 (5)	0.4012 (3)	0.0390 (9)
C6	0.5142 (3)	0.0633 (5)	0.1513 (3)	0.0244 (8)
N2	0.6067 (3)	0.0572 (5)	0.1289 (2)	0.0283 (7)
C5	0.7000 (4)	0.1010 (5)	0.3106 (3)	0.0294 (9)
C10	0.1263 (4)	−0.0412 (8)	0.1036 (3)	0.0467 (13)
H10	0.0714	−0.1346	0.0929	0.056*
N3	0.4086 (3)	0.0347 (5)	0.0812 (2)	0.0307 (8)
H3	0.4002	0.0097	0.0038	0.11 (3)*
C4	0.7091 (3)	0.0741 (5)	0.2149 (3)	0.0255 (8)
C9	0.2266 (4)	−0.0716 (6)	0.0859 (3)	0.0320 (9)
C3	0.8190 (4)	0.0674 (6)	0.2134 (3)	0.0354 (10)
H3A	0.8303	0.0447	0.1507	0.042*
C7	0.3078 (3)	0.0625 (6)	0.1015 (3)	0.0264 (8)
C8	0.2863 (4)	0.2307 (6)	0.1358 (3)	0.0359 (10)
H8	0.3407	0.3248	0.1466	0.043*
C2	0.9120 (4)	0.0950 (6)	0.3064 (4)	0.0409 (11)
H2	0.9885	0.0937	0.3079	0.049*
C11	0.1872 (4)	0.2608 (8)	0.1538 (4)	0.0471 (12)
H11	0.1743	0.3748	0.1779	0.056*
C12	0.1068 (4)	0.1272 (9)	0.1372 (4)	0.0534 (15)
H12	0.0379	0.1496	0.1486	0.064*

	U11	U22	U33	U12	U13	U23
Se1	0.0303 (3)	0.0541 (4)	0.0266 (3)	−0.00181 (18)	0.0184 (2)	−0.00480 (18)
Br1	0.0459 (4)	0.0368 (4)	0.0550 (4)	−0.0067 (2)	0.0055 (3)	0.0005 (2)
C1	0.028 (2)	0.044 (2)	0.034 (2)	0.000 (2)	−0.0008 (18)	−0.0034 (19)
N1	0.038 (2)	0.045 (2)	0.0263 (18)	−0.0011 (17)	0.0045 (16)	−0.0022 (16)
C6	0.0217 (19)	0.0271 (19)	0.0281 (19)	−0.0004 (15)	0.0135 (16)	−0.0024 (15)
N2	0.0222 (17)	0.0396 (18)	0.0269 (17)	−0.0023 (14)	0.0137 (14)	−0.0037 (14)
C5	0.034 (2)	0.028 (2)	0.028 (2)	0.0000 (16)	0.0148 (18)	−0.0021 (15)
C10	0.022 (2)	0.075 (4)	0.041 (3)	−0.009 (2)	0.010 (2)	0.016 (2)
N3	0.0199 (17)	0.047 (2)	0.0287 (17)	−0.0016 (15)	0.0134 (14)	−0.0077 (15)
C4	0.022 (2)	0.0283 (19)	0.0254 (19)	−0.0012 (15)	0.0082 (16)	−0.0003 (15)
C9	0.024 (2)	0.044 (2)	0.027 (2)	−0.0020 (18)	0.0082 (17)	0.0063 (17)
C3	0.024 (2)	0.048 (3)	0.039 (2)	0.0023 (18)	0.0179 (18)	0.0001 (19)
C7	0.0174 (18)	0.042 (2)	0.0230 (18)	−0.0001 (16)	0.0111 (15)	−0.0002 (16)
C8	0.031 (2)	0.042 (2)	0.039 (2)	0.0025 (19)	0.0177 (19)	−0.0041 (19)
C2	0.023 (2)	0.049 (3)	0.046 (3)	−0.0020 (18)	0.008 (2)	0.001 (2)
C11	0.038 (3)	0.067 (3)	0.040 (3)	0.015 (2)	0.018 (2)	−0.007 (2)
C12	0.028 (3)	0.098 (4)	0.041 (3)	0.010 (3)	0.021 (2)	0.005 (3)

Se1—C5	1.886 (4)	N3—C7	1.410 (5)
Se1—C6	1.920 (4)	N3—H3	1.0555
Br1—C9	1.897 (5)	C4—C3	1.387 (6)
C1—N1	1.340 (7)	C9—C7	1.384 (6)
C1—C2	1.384 (7)	C3—C2	1.387 (6)
C1—H1	0.9500	C3—H3A	0.9500
N1—C5	1.334 (6)	C7—C8	1.404 (6)
C6—N2	1.309 (5)	C8—C11	1.375 (6)
C6—N3	1.328 (5)	C8—H8	0.9500
N2—C4	1.388 (5)	C2—H2	0.9500
C5—C4	1.390 (6)	C11—C12	1.372 (8)
C10—C9	1.388 (7)	C11—H11	0.9500
C10—C12	1.393 (8)	C12—H12	0.9500
C10—H10	0.9500
C5—Se1—C6	83.98 (17)	C7—C9—C10	121.1 (4)
N1—C1—C2	123.6 (4)	C7—C9—Br1	119.4 (3)
N1—C1—H1	118.2	C10—C9—Br1	119.5 (4)
C2—C1—H1	118.2	C4—C3—C2	117.9 (4)
C5—N1—C1	115.4 (4)	C4—C3—H3A	121.0
N2—C6—N3	123.0 (3)	C2—C3—H3A	121.0
N2—C6—Se1	114.5 (3)	C9—C7—C8	118.3 (4)
N3—C6—Se1	122.3 (3)	C9—C7—N3	121.6 (4)
C6—N2—C4	113.9 (3)	C8—C7—N3	120.1 (4)
N1—C5—C4	125.7 (4)	C11—C8—C7	120.7 (5)
N1—C5—Se1	123.5 (3)	C11—C8—H8	119.6
C4—C5—Se1	110.7 (3)	C7—C8—H8	119.6
C9—C10—C12	119.5 (5)	C1—C2—C3	119.7 (4)
C9—C10—H10	120.3	C1—C2—H2	120.1
C12—C10—H10	120.3	C3—C2—H2	120.1
C6—N3—C7	123.2 (3)	C12—C11—C8	120.5 (5)
C6—N3—H3	117.4	C12—C11—H11	119.8
C7—N3—H3	118.6	C8—C11—H11	119.8
C3—C4—N2	125.6 (4)	C11—C12—C10	120.0 (4)
C3—C4—C5	117.5 (4)	C11—C12—H12	120.0
N2—C4—C5	116.8 (4)	C10—C12—H12	120.0
C2—C1—N1—C5	−1.6 (7)	C12—C10—C9—C7	0.3 (7)
C5—Se1—C6—N2	−0.2 (3)	C12—C10—C9—Br1	−179.6 (4)
C5—Se1—C6—N3	175.3 (4)	N2—C4—C3—C2	177.1 (4)
N3—C6—N2—C4	−174.2 (4)	C5—C4—C3—C2	−2.5 (6)
Se1—C6—N2—C4	1.3 (4)	C10—C9—C7—C8	0.0 (6)
C1—N1—C5—C4	0.1 (6)	Br1—C9—C7—C8	179.8 (3)
C1—N1—C5—Se1	−179.5 (3)	C10—C9—C7—N3	−178.3 (4)
C6—Se1—C5—N1	178.7 (4)	Br1—C9—C7—N3	1.5 (5)
C6—Se1—C5—C4	−0.9 (3)	C6—N3—C7—C9	−125.4 (4)
N2—C6—N3—C7	−172.0 (4)	C6—N3—C7—C8	56.4 (6)
Se1—C6—N3—C7	12.8 (6)	C9—C7—C8—C11	0.3 (6)
C6—N2—C4—C3	178.2 (4)	N3—C7—C8—C11	178.7 (4)
C6—N2—C4—C5	−2.1 (5)	N1—C1—C2—C3	0.9 (8)
N1—C5—C4—C3	2.0 (6)	C4—C3—C2—C1	1.2 (7)
Se1—C5—C4—C3	−178.4 (3)	C7—C8—C11—C12	−0.9 (7)
N1—C5—C4—N2	−177.7 (4)	C8—C11—C12—C10	1.1 (8)
Se1—C5—C4—N2	1.9 (4)	C9—C10—C12—C11	−0.8 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2i	1.06	1.88	2.933 (4)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2i	1.06	1.88	2.933 (4)	174

Symmetry code: (i) .