A second monoclinic polymorph of (E)-phen-yl(pyridin-2-yl)methanone oxime.

The title compound, C(12)H(10)N(2)O, a second monoclinic poly-morph of (E)-phen-yl(pyridin-2-yl)methanone oxime crystallizes in the space group P2(1)/n (Z = 4). The previously reported polymorph [Taga et al. (1990 ▶). Acta Cryst. C46, 2241-2243] occurs in the space group C2/c (Z = 8). In the crystal, pairs of bifurcated O-H⋯(N,O) hydrogen bonds link the mol-ecules into inversion dimers. The dimers are linked by C-H⋯π inter-actions, forming a linear arrangement. The dihedral angle between the pyridine and phenyl rings is 67.70 (8)°.

Related literature

For properties of oximes, see: Custot et al. (1996 ▶); Turner & Ciufolini (2011 ▶); Abele et al. (2003 ▶). For the use of complexes of pyridyl oximes with a variety of transition metals in supra­molecular and materials chemistry, see: Shokrollahi et al. (2008 ▶); Martinez et al. (2008 ▶). For the previously reported polymorph, see: Taga et al. (1990 ▶).

Experimental

Crystal data

C12H10N2O

M = 198.22

Monoclinic,

a = 5.6732 (4) Å

b = 23.257 (2) Å

c = 7.4516 (5) Å

β = 97.743 (7)°

V = 974.21 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 130 K

0.55 × 0.31 × 0.06 mm

Data collection

Agilent Xcalibur (Atlas, Gemini) diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2011) ▶, based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.976, T max = 0.995

4256 measured reflections

1918 independent reflections

1559 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.04

1918 reflections

139 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813002377/zj2100sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002377/zj2100Isup2.hkl

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

C12H10N2O	F(000) = 416
Mr = 198.22	Dx = 1.351 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.6732 (4) Å	Cell parameters from 1437 reflections
b = 23.257 (2) Å	θ = 3.5–26.0°
c = 7.4516 (5) Å	µ = 0.09 mm−1
β = 97.743 (7)°	T = 130 K
V = 974.21 (13) Å3	Lamina, pale pink
Z = 4	0.55 × 0.31 × 0.06 mm

Agilent Xcalibur (Atlas, Gemini) diffractometer	1918 independent reflections
Graphite monochromator	1559 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.023
ω scans	θmax = 26.1°, θmin = 3.5°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)]	h = −7→6
Tmin = 0.976, Tmax = 0.995	k = −28→25
4256 measured reflections	l = −9→6

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.3722P] where P = (Fo2 + 2Fc2)/3
1918 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.22 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	−0.01894 (19)	0.05043 (5)	0.85027 (15)	0.0286 (3)
N1	0.6746 (2)	0.13409 (6)	1.14331 (18)	0.0290 (3)
N2	0.1685 (2)	0.04881 (5)	0.99337 (16)	0.0233 (3)
C1	0.2991 (2)	0.13583 (6)	0.84972 (19)	0.0198 (3)
C2	0.1085 (3)	0.17379 (7)	0.8370 (2)	0.0243 (4)
H2	−0.0075	0.1701	0.917	0.029*
C3	0.0870 (3)	0.21697 (7)	0.7082 (2)	0.0261 (4)
H3	−0.0419	0.2433	0.7016	0.031*
C4	0.2528 (3)	0.22192 (7)	0.5889 (2)	0.0263 (4)
H4	0.2369	0.2513	0.4996	0.032*
C5	0.4416 (3)	0.18395 (7)	0.6003 (2)	0.0279 (4)
H5	0.5546	0.1871	0.5176	0.034*
C6	0.4672 (3)	0.14138 (7)	0.7312 (2)	0.0249 (4)
H6	0.5994	0.116	0.74	0.03*
C7	0.3204 (2)	0.08948 (6)	0.98862 (19)	0.0201 (3)
C8	0.5261 (3)	0.08876 (7)	1.13697 (19)	0.0219 (3)
C9	0.5601 (3)	0.04407 (7)	1.2600 (2)	0.0308 (4)
H9	0.4548	0.0121	1.2517	0.037*
C10	0.7525 (3)	0.04717 (8)	1.3962 (2)	0.0382 (5)
H10	0.7786	0.0173	1.4835	0.046*
C11	0.9048 (3)	0.09311 (8)	1.4052 (2)	0.0346 (4)
H11	1.0369	0.0958	1.4978	0.042*
C12	0.8605 (3)	0.13487 (8)	1.2768 (2)	0.0335 (4)
H12	0.9671	0.1665	1.2816	0.04*
H1D	−0.097 (3)	0.0196 (8)	0.878 (3)	0.05*

	U11	U22	U33	U12	U13	U23
O1	0.0289 (6)	0.0258 (6)	0.0284 (6)	−0.0061 (5)	−0.0054 (5)	0.0065 (5)
N1	0.0306 (7)	0.0282 (8)	0.0266 (7)	−0.0043 (6)	−0.0018 (6)	−0.0015 (6)
N2	0.0250 (7)	0.0224 (7)	0.0215 (6)	0.0002 (5)	−0.0007 (5)	0.0012 (5)
C1	0.0225 (7)	0.0183 (8)	0.0179 (7)	−0.0019 (6)	0.0000 (6)	−0.0007 (6)
C2	0.0257 (8)	0.0235 (8)	0.0250 (8)	0.0008 (6)	0.0081 (6)	0.0014 (6)
C3	0.0271 (8)	0.0197 (8)	0.0312 (9)	0.0029 (6)	0.0033 (6)	0.0017 (7)
C4	0.0302 (8)	0.0242 (8)	0.0236 (8)	−0.0054 (7)	0.0004 (6)	0.0055 (6)
C5	0.0256 (8)	0.0350 (10)	0.0242 (8)	−0.0023 (7)	0.0069 (6)	0.0041 (7)
C6	0.0201 (7)	0.0286 (9)	0.0259 (8)	0.0023 (7)	0.0027 (6)	0.0020 (7)
C7	0.0233 (7)	0.0184 (7)	0.0193 (7)	0.0030 (6)	0.0050 (6)	−0.0007 (6)
C8	0.0243 (8)	0.0227 (8)	0.0192 (7)	0.0038 (6)	0.0049 (6)	−0.0009 (6)
C9	0.0350 (9)	0.0263 (9)	0.0316 (9)	0.0033 (7)	0.0062 (7)	0.0077 (7)
C10	0.0451 (10)	0.0414 (11)	0.0279 (9)	0.0161 (9)	0.0049 (8)	0.0138 (8)
C11	0.0298 (9)	0.0475 (11)	0.0246 (8)	0.0082 (8)	−0.0029 (7)	−0.0042 (8)
C12	0.0301 (9)	0.0377 (10)	0.0308 (9)	−0.0060 (8)	−0.0026 (7)	−0.0063 (8)

O1—N2	1.4015 (15)	C4—H4	0.95
O1—H1D	0.882 (15)	C5—C6	1.384 (2)
N1—C8	1.346 (2)	C5—H5	0.95
N1—C12	1.349 (2)	C6—H6	0.95
N2—C7	1.2832 (19)	C7—C8	1.495 (2)
C1—C2	1.389 (2)	C8—C9	1.382 (2)
C1—C6	1.391 (2)	C9—C10	1.388 (2)
C1—C7	1.488 (2)	C9—H9	0.95
C2—C3	1.383 (2)	C10—C11	1.370 (3)
C2—H2	0.95	C10—H10	0.95
C3—C4	1.382 (2)	C11—C12	1.363 (3)
C3—H3	0.95	C11—H11	0.95
C4—C5	1.382 (2)	C12—H12	0.95
N2—O1—H1D	98.8 (13)	C1—C6—H6	120.1
C8—N1—C12	117.37 (14)	N2—C7—C1	124.14 (13)
C7—N2—O1	113.76 (12)	N2—C7—C8	115.55 (13)
C2—C1—C6	119.46 (14)	C1—C7—C8	120.29 (13)
C2—C1—C7	119.83 (13)	N1—C8—C9	122.33 (14)
C6—C1—C7	120.71 (13)	N1—C8—C7	116.07 (13)
C3—C2—C1	120.25 (14)	C9—C8—C7	121.60 (14)
C3—C2—H2	119.9	C8—C9—C10	118.12 (16)
C1—C2—H2	119.9	C8—C9—H9	120.9
C4—C3—C2	120.15 (14)	C10—C9—H9	120.9
C4—C3—H3	119.9	C11—C10—C9	120.34 (16)
C2—C3—H3	119.9	C11—C10—H10	119.8
C5—C4—C3	119.75 (15)	C9—C10—H10	119.8
C5—C4—H4	120.1	C12—C11—C10	117.75 (15)
C3—C4—H4	120.1	C12—C11—H11	121.1
C4—C5—C6	120.48 (15)	C10—C11—H11	121.1
C4—C5—H5	119.8	N1—C12—C11	124.08 (16)
C6—C5—H5	119.8	N1—C12—H12	118
C5—C6—C1	119.89 (14)	C11—C12—H12	118
C5—C6—H6	120.1
C6—C1—C2—C3	−0.4 (2)	C6—C1—C7—C8	64.41 (19)
C7—C1—C2—C3	−179.93 (13)	C12—N1—C8—C9	−0.5 (2)
C1—C2—C3—C4	1.3 (2)	C12—N1—C8—C7	179.37 (14)
C2—C3—C4—C5	−0.7 (2)	N2—C7—C8—N1	−174.03 (13)
C3—C4—C5—C6	−0.6 (2)	C1—C7—C8—N1	4.9 (2)
C4—C5—C6—C1	1.5 (2)	N2—C7—C8—C9	5.8 (2)
C2—C1—C6—C5	−0.9 (2)	C1—C7—C8—C9	−175.19 (14)
C7—C1—C6—C5	178.56 (14)	N1—C8—C9—C10	1.2 (2)
O1—N2—C7—C1	2.2 (2)	C7—C8—C9—C10	−178.63 (15)
O1—N2—C7—C8	−178.89 (12)	C8—C9—C10—C11	−0.9 (3)
C2—C1—C7—N2	62.8 (2)	C9—C10—C11—C12	−0.1 (3)
C6—C1—C7—N2	−116.71 (17)	C8—N1—C12—C11	−0.6 (3)
C2—C1—C7—C8	−116.09 (16)	C10—C11—C12—N1	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···N2i	0.88 (2)	1.93 (2)	2.7696 (17)	159 (2)
O1—H1D···O1i	0.88 (2)	2.61 (2)	3.225 (2)	127 (2)
C11—H11···Cgii	0.95	2.78	3.5453 (18)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯N2i	0.88 (2)	1.93 (2)	2.7696 (17)	159 (2)
O1—H1D⋯O1i	0.88 (2)	2.61 (2)	3.225 (2)	127 (2)
C11—H11⋯Cg ii	0.95	2.78	3.5453 (18)	139

Symmetry codes: (i) ; (ii) .