5-Amino-3-(4-pyrid-yl)isoxazole.

In the title compound, C(8)H(7)N(3)O, there are two independent mol-ecules in the asymmetric unit, in which the angles between the pyridine ring and the isoxazole ring are 35.8 (6) and 10.6 (2)°. The crystal packing is stabilized by N-H⋯N hydrogen bonds, which result in the mol-ecules forming a two-dimensional supra-molecular layer.

Related literature

The title compound was prepared according to a known procedure (Schmidt et al., 1966 ▶). For hydrogen-bond motif definitions, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H7N3O

M = 161.17

Monoclinic,

a = 14.6411 (13) Å

b = 10.9272 (10) Å

c = 10.0060 (9) Å

β = 106.9870 (10)°

V = 1531.0 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 187 (2) K

0.42 × 0.18 × 0.10 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.990

8396 measured reflections

3018 independent reflections

2509 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.02

3018 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706309X/bv2079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706309X/bv2079Isup2.hkl

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

C8H7N3O	F000 = 672
Mr = 161.17	Dx = 1.398 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2830 reflections
a = 14.6411 (13) Å	θ = 2.4–25.9º
b = 10.9272 (10) Å	µ = 0.10 mm−1
c = 10.0060 (9) Å	T = 187 (2) K
β = 106.9870 (10)º	Block, colourless
V = 1531.0 (2) Å3	0.42 × 0.18 × 0.10 mm
Z = 8

Bruker APEX CCD area-detector diffractometer	3018 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 187(2) K	θmax = 26.0º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −18→14
Tmin = 0.960, Tmax = 0.990	k = −10→13
8396 measured reflections	l = −12→12

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.07P)2 + 0.2315P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.23 e Å−3
3018 reflections	Δρmin = −0.23 e Å−3
218 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (10)
Secondary atom site location: difference Fourier map

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
O1	0.46333 (7)	0.85688 (9)	0.20940 (11)	0.0346 (3)
O2	0.00420 (8)	0.88480 (9)	0.77638 (11)	0.0336 (3)
N1	0.79693 (9)	0.83254 (13)	−0.07659 (13)	0.0383 (3)
N2	0.52225 (9)	0.80823 (11)	0.13072 (13)	0.0337 (3)
N3	0.44141 (10)	1.03237 (12)	0.31848 (14)	0.0388 (3)
H3A	0.3946	0.9950	0.3407	0.047*
H3B	0.4558	1.1086	0.3447	0.047*
N4	0.28672 (10)	0.90935 (13)	0.40458 (14)	0.0398 (3)
N5	0.06798 (9)	0.93321 (11)	0.70626 (14)	0.0359 (3)
N6	−0.06051 (10)	0.70441 (11)	0.81376 (14)	0.0377 (3)
H6A	−0.0927	0.7458	0.8606	0.045*
H6B	−0.0675	0.6246	0.8048	0.045*
C1	0.72429 (11)	0.75481 (15)	−0.08875 (15)	0.0358 (4)
H1	0.7222	0.6830	−0.1430	0.043*
C2	0.65244 (11)	0.77244 (14)	−0.02749 (15)	0.0346 (4)
H2	0.6026	0.7141	−0.0398	0.042*
C3	0.65383 (10)	0.87660 (13)	0.05244 (14)	0.0271 (3)
C4	0.72841 (11)	0.95824 (14)	0.06540 (16)	0.0368 (4)
H4	0.7322	1.0310	0.1188	0.044*
C5	0.79718 (12)	0.93253 (15)	−0.00027 (18)	0.0419 (4)
H5	0.8477	0.9896	0.0096	0.050*
C6	0.58040 (10)	0.89855 (13)	0.12468 (13)	0.0270 (3)
C7	0.49043 (11)	0.97363 (13)	0.24510 (14)	0.0289 (3)
C8	0.56482 (10)	1.00383 (13)	0.19470 (14)	0.0292 (3)
H8	0.5984	1.0793	0.2049	0.035*
C9	0.29569 (12)	0.80896 (15)	0.48351 (17)	0.0399 (4)
H9	0.3461	0.7540	0.4845	0.048*
C10	0.23625 (11)	0.77991 (14)	0.56385 (16)	0.0351 (4)
H10	0.2452	0.7065	0.6170	0.042*
C11	0.16304 (10)	0.86076 (13)	0.56504 (14)	0.0286 (3)
C12	0.15291 (11)	0.96543 (14)	0.48390 (15)	0.0331 (4)
H12	0.1038	1.0227	0.4820	0.040*
C13	0.21520 (12)	0.98536 (15)	0.40568 (16)	0.0379 (4)
H13	0.2068	1.0570	0.3496	0.045*
C14	0.09696 (10)	0.83758 (13)	0.65003 (14)	0.0272 (3)
C15	0.05754 (11)	0.72799 (13)	0.67909 (15)	0.0310 (3)
H15	0.0689	0.6476	0.6514	0.037*
C16	−0.00128 (10)	0.76260 (13)	0.75652 (14)	0.0274 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0346 (6)	0.0288 (6)	0.0488 (6)	−0.0019 (4)	0.0251 (5)	−0.0016 (5)
O2	0.0403 (6)	0.0237 (5)	0.0474 (6)	−0.0025 (4)	0.0294 (5)	−0.0020 (4)
N1	0.0352 (7)	0.0459 (8)	0.0394 (7)	0.0043 (6)	0.0198 (6)	0.0003 (6)
N2	0.0330 (7)	0.0304 (7)	0.0443 (7)	0.0000 (5)	0.0216 (6)	−0.0034 (5)
N3	0.0443 (8)	0.0306 (7)	0.0545 (8)	−0.0018 (6)	0.0347 (7)	−0.0025 (6)
N4	0.0369 (8)	0.0452 (8)	0.0452 (7)	−0.0045 (6)	0.0242 (6)	−0.0018 (6)
N5	0.0415 (8)	0.0270 (7)	0.0502 (8)	−0.0038 (6)	0.0303 (6)	0.0000 (6)
N6	0.0488 (8)	0.0247 (7)	0.0527 (8)	−0.0031 (6)	0.0353 (7)	−0.0018 (6)
C1	0.0382 (9)	0.0391 (9)	0.0328 (8)	0.0022 (7)	0.0146 (7)	−0.0053 (7)
C2	0.0331 (8)	0.0370 (9)	0.0361 (8)	−0.0039 (7)	0.0138 (7)	−0.0038 (7)
C3	0.0270 (7)	0.0287 (8)	0.0268 (7)	0.0030 (6)	0.0098 (6)	0.0026 (6)
C4	0.0364 (9)	0.0340 (9)	0.0458 (9)	−0.0031 (7)	0.0209 (7)	−0.0060 (7)
C5	0.0382 (9)	0.0418 (9)	0.0538 (10)	−0.0065 (7)	0.0263 (8)	−0.0063 (8)
C6	0.0251 (7)	0.0283 (7)	0.0284 (7)	0.0005 (6)	0.0088 (6)	0.0043 (6)
C7	0.0321 (8)	0.0258 (8)	0.0313 (7)	0.0020 (6)	0.0129 (6)	0.0030 (6)
C8	0.0308 (8)	0.0269 (7)	0.0343 (7)	−0.0030 (6)	0.0164 (6)	−0.0006 (6)
C9	0.0351 (9)	0.0421 (10)	0.0491 (9)	0.0051 (7)	0.0225 (7)	0.0015 (8)
C10	0.0353 (8)	0.0328 (8)	0.0417 (8)	0.0037 (7)	0.0181 (7)	0.0040 (7)
C11	0.0270 (7)	0.0300 (8)	0.0312 (7)	−0.0035 (6)	0.0124 (6)	−0.0026 (6)
C12	0.0336 (8)	0.0314 (8)	0.0398 (8)	0.0011 (6)	0.0193 (7)	0.0023 (7)
C13	0.0431 (9)	0.0347 (9)	0.0423 (9)	−0.0030 (7)	0.0225 (7)	0.0038 (7)
C14	0.0266 (7)	0.0268 (7)	0.0301 (7)	0.0015 (6)	0.0113 (6)	0.0017 (6)
C15	0.0387 (8)	0.0223 (7)	0.0386 (8)	0.0016 (6)	0.0214 (7)	0.0006 (6)
C16	0.0309 (7)	0.0227 (7)	0.0322 (7)	0.0010 (6)	0.0150 (6)	0.0016 (6)

O1—C7	1.3527 (17)	C3—C4	1.386 (2)
O1—N2	1.4295 (14)	C3—C6	1.4798 (18)
O2—C16	1.3490 (17)	C4—C5	1.382 (2)
O2—N5	1.4237 (14)	C4—H4	0.9500
N1—C5	1.332 (2)	C5—H5	0.9500
N1—C1	1.339 (2)	C6—C8	1.3999 (19)
N2—C6	1.3164 (18)	C7—C8	1.3677 (19)
N3—C7	1.3319 (18)	C8—H8	0.9500
N3—H3A	0.8800	C9—C10	1.383 (2)
N3—H3B	0.8800	C9—H9	0.9500
N4—C9	1.336 (2)	C10—C11	1.392 (2)
N4—C13	1.339 (2)	C10—H10	0.9500
N5—C14	1.3145 (17)	C11—C12	1.385 (2)
N6—C16	1.3322 (18)	C11—C14	1.4847 (18)
N6—H6A	0.8800	C12—C13	1.3816 (19)
N6—H6B	0.8800	C12—H12	0.9500
C1—C2	1.377 (2)	C13—H13	0.9500
C1—H1	0.9500	C14—C15	1.3963 (19)
C2—C3	1.388 (2)	C15—C16	1.3692 (19)
C2—H2	0.9500	C15—H15	0.9500
C7—O1—N2	108.58 (10)	N3—C7—O1	115.87 (13)
C16—O2—N5	108.34 (10)	N3—C7—C8	134.62 (14)
C5—N1—C1	116.20 (13)	O1—C7—C8	109.51 (12)
C6—N2—O1	104.42 (11)	C7—C8—C6	104.48 (12)
C7—N3—H3A	120.0	C7—C8—H8	127.8
C7—N3—H3B	120.0	C6—C8—H8	127.8
H3A—N3—H3B	120.0	N4—C9—C10	124.22 (15)
C9—N4—C13	116.52 (13)	N4—C9—H9	117.9
C14—N5—O2	104.82 (10)	C10—C9—H9	117.9
C16—N6—H6A	120.0	C9—C10—C11	118.44 (14)
C16—N6—H6B	120.0	C9—C10—H10	120.8
H6A—N6—H6B	120.0	C11—C10—H10	120.8
N1—C1—C2	124.11 (14)	C12—C11—C10	118.03 (13)
N1—C1—H1	117.9	C12—C11—C14	120.03 (13)
C2—C1—H1	117.9	C10—C11—C14	121.94 (13)
C1—C2—C3	119.13 (14)	C13—C12—C11	119.13 (14)
C1—C2—H2	120.4	C13—C12—H12	120.4
C3—C2—H2	120.4	C11—C12—H12	120.4
C4—C3—C2	117.40 (13)	N4—C13—C12	123.65 (15)
C4—C3—C6	120.98 (13)	N4—C13—H13	118.2
C2—C3—C6	121.60 (13)	C12—C13—H13	118.2
C5—C4—C3	119.20 (14)	N5—C14—C15	112.83 (12)
C5—C4—H4	120.4	N5—C14—C11	117.08 (12)
C3—C4—H4	120.4	C15—C14—C11	130.08 (12)
N1—C5—C4	123.96 (15)	C16—C15—C14	104.33 (12)
N1—C5—H5	118.0	C16—C15—H15	127.8
C4—C5—H5	118.0	C14—C15—H15	127.8
N2—C6—C8	113.02 (12)	N6—C16—O2	115.30 (12)
N2—C6—C3	118.22 (13)	N6—C16—C15	135.03 (14)
C8—C6—C3	128.72 (13)	O2—C16—C15	109.67 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N4	0.88	2.09	2.970 (2)	177
N3—H3B···N2i	0.88	2.20	3.077 (2)	169
N6—H6A···N1ii	0.88	2.12	2.976 (2)	164
N6—H6B···N5iii	0.88	2.09	2.970 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N4	0.88	2.09	2.970 (2)	177
N3—H3B⋯N2i	0.88	2.20	3.077 (2)	169
N6—H6A⋯N1ii	0.88	2.12	2.976 (2)	164
N6—H6B⋯N5iii	0.88	2.09	2.970 (2)	174

Symmetry codes: (i) ; (ii) ; (iii) .