2-Phenyl-imidazo[1,2-a]pyridine-3-carbaldehyde.

In the title compound, C(14)H(10)N(2)O, the dihedral angle between the imidazo[1,2-a]pyridine and phenyl rings is 28.61 (4)° The mol-ecules are connected into broad chains parallel to the a axis by weak C-H⋯O and C-H⋯N hydrogen bonds. The linking of the ribbons is provided by π-π stacking inter-actions between neighbouring pyridine rings, with a centroid-centroid distance of 3.7187 (7) Å.

Related literature

For general background, see Anaflous et al. (2008 ▶) and references therein. For related literature, see: Meth-Cohn & Stanforth (1991 ▶).

Experimental

Crystal data

C14H10N2O

M = 222.2

Orthorhombic,

a = 13.0640 (3) Å

b = 7.4162 (2) Å

c = 21.6698 (6) Å

V = 2099.48 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.57 × 0.40 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector

Absorption correction: none

25795 measured reflections

2196 independent reflections

1305 reflections with I > 3σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.04

2196 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2000 (Petříček et al., 2000 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2000.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011306/bg2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011306/bg2180Isup2.hkl

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

C14H10N2O	F000 = 928
Mr = 222.2	Dx = 1.406 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8746 reflections
a = 13.0640 (3) Å	θ = 2.7–26.5º
b = 7.4162 (2) Å	µ = 0.09 mm−1
c = 21.6698 (6) Å	T = 120 K
V = 2099.48 (9) Å3	Prism, colourless
Z = 8	0.57 × 0.40 × 0.24 mm

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector	2196 independent reflections
Radiation source: X-ray tube	1305 reflections with I > 3σ(I)
Monochromator: graphite	Rint = 0.049
Detector resolution: 8.3438 pixels mm-1	θmax = 26.6º
T = 120 K	θmin = 3.1º
Rotation method data acquisition using ω scans	h = −16→16
Absorption correction: none	k = −9→9
25795 measured reflections	l = −27→27

Refinement on F2	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
wR(F2) = 0.077	(Δ/σ)max = 0.007
S = 1.04	Δρmax = 0.15 e Å−3
2196 reflections	Δρmin = −0.16 e Å−3
154 parameters	Extinction correction: none
36 constraints

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.All the H atoms were discernible in difference Fourier maps and could be refined to reasonable geometry. According to standard procedures for organic compounds the H atoms bonded to C atoms were constrained to ideal positions. The isotropic atomic displacement parameters of hydrogen atoms were evaluated as 1.2*Ueq of the parent atom.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
N1	0.38579 (8)	0.13099 (13)	0.06669 (5)	0.0227 (3)
N2	0.22707 (8)	0.09004 (13)	0.02784 (5)	0.0204 (3)
O1	0.03531 (7)	0.19646 (11)	0.08623 (4)	0.0297 (3)
C1	0.31590 (10)	0.18666 (16)	0.10870 (6)	0.0208 (4)
C2	0.33161 (10)	0.07295 (16)	0.01765 (6)	0.0207 (4)
C3	0.21543 (10)	0.16659 (16)	0.08658 (6)	0.0204 (4)
C4	0.36597 (11)	−0.00163 (16)	−0.03801 (6)	0.0235 (4)
C5	0.29491 (10)	−0.05736 (17)	−0.08037 (7)	0.0243 (4)
C6	0.18958 (10)	−0.03859 (17)	−0.06861 (6)	0.0247 (4)
C7	0.15617 (10)	0.03543 (16)	−0.01503 (6)	0.0236 (4)
C8	0.35054 (10)	0.25310 (16)	0.16940 (6)	0.0214 (4)
C9	0.29235 (10)	0.23521 (17)	0.22302 (7)	0.0238 (4)
C10	0.32855 (11)	0.30105 (17)	0.27874 (7)	0.0274 (5)
C11	0.42372 (11)	0.38290 (17)	0.28223 (6)	0.0283 (5)
C12	0.48307 (11)	0.39863 (17)	0.22959 (6)	0.0282 (4)
C13	0.44708 (10)	0.33402 (16)	0.17344 (6)	0.0242 (4)
C14	0.11885 (10)	0.22273 (16)	0.11073 (7)	0.0245 (4)
H4	0.437543	−0.014444	−0.047038	0.0282*
H5	0.318903	−0.109503	−0.118246	0.0292*
H6	0.139117	−0.077351	−0.097954	0.0296*
H7	0.084111	0.048834	−0.007645	0.0283*
H9	0.226757	0.177012	0.221555	0.0286*
H10	0.287357	0.289867	0.315233	0.0329*
H11	0.448433	0.4285	0.320918	0.0339*
H12	0.549259	0.454408	0.232038	0.0339*
H13	0.489068	0.345338	0.137292	0.0291*
H14	0.108688	0.287015	0.148695	0.0294*

	U11	U22	U33	U12	U13	U23
N1	0.0207 (6)	0.0225 (5)	0.0249 (6)	0.0004 (5)	0.0004 (5)	0.0017 (5)
N2	0.0196 (6)	0.0177 (5)	0.0239 (6)	−0.0005 (5)	−0.0001 (5)	0.0031 (5)
O1	0.0200 (6)	0.0315 (5)	0.0376 (6)	0.0000 (4)	−0.0002 (5)	0.0024 (5)
C1	0.0221 (7)	0.0149 (7)	0.0255 (8)	0.0007 (6)	0.0019 (6)	0.0052 (6)
C2	0.0192 (7)	0.0170 (6)	0.0259 (8)	−0.0002 (6)	0.0015 (6)	0.0051 (6)
C3	0.0211 (7)	0.0179 (6)	0.0223 (7)	−0.0008 (6)	0.0022 (6)	0.0026 (6)
C4	0.0219 (8)	0.0224 (7)	0.0263 (8)	−0.0005 (6)	0.0024 (6)	0.0027 (6)
C5	0.0281 (8)	0.0201 (7)	0.0248 (8)	−0.0015 (6)	0.0020 (6)	0.0031 (6)
C6	0.0245 (8)	0.0220 (7)	0.0275 (8)	−0.0044 (6)	−0.0037 (6)	0.0023 (6)
C7	0.0194 (8)	0.0225 (7)	0.0289 (8)	−0.0025 (6)	−0.0031 (6)	0.0043 (6)
C8	0.0228 (8)	0.0155 (6)	0.0260 (8)	0.0027 (6)	−0.0010 (6)	0.0032 (5)
C9	0.0216 (8)	0.0212 (7)	0.0288 (8)	−0.0003 (6)	−0.0001 (7)	0.0034 (6)
C10	0.0313 (8)	0.0267 (7)	0.0242 (8)	0.0049 (7)	0.0017 (7)	0.0034 (6)
C11	0.0330 (8)	0.0255 (7)	0.0263 (8)	0.0053 (7)	−0.0057 (7)	−0.0006 (6)
C12	0.0266 (8)	0.0242 (7)	0.0339 (8)	−0.0021 (6)	−0.0043 (7)	0.0013 (7)
C13	0.0243 (8)	0.0222 (7)	0.0263 (8)	0.0009 (6)	0.0007 (6)	0.0032 (6)
C14	0.0262 (8)	0.0201 (7)	0.0271 (8)	0.0008 (7)	0.0032 (7)	0.0041 (6)

N1—C1	1.3537 (16)	C6—H6	0.9600
N1—C2	1.3475 (16)	C7—H7	0.9600
N2—C2	1.3893 (16)	C8—C9	1.3949 (19)
N2—C3	1.4020 (17)	C8—C13	1.3994 (18)
N2—C7	1.3731 (17)	C9—C10	1.386 (2)
O1—C14	1.2293 (16)	C9—H9	0.9600
C1—C3	1.4052 (18)	C10—C11	1.3857 (19)
C1—C8	1.4758 (18)	C10—H10	0.9600
C2—C4	1.4008 (18)	C11—C12	1.3840 (19)
C3—C14	1.4279 (18)	C11—H11	0.9600
C4—C5	1.3693 (19)	C12—C13	1.3897 (19)
C4—H4	0.9600	C12—H12	0.9600
C5—C6	1.4063 (18)	C13—H13	0.9600
C5—H5	0.9600	C14—H14	0.9600
C6—C7	1.3564 (19)
C1—N1—C2	105.87 (10)	N2—C7—H7	121.20
C2—N2—C3	106.74 (10)	C6—C7—H7	120.02
C2—N2—C7	121.92 (11)	C1—C8—C9	122.93 (12)
C3—N2—C7	131.34 (11)	C1—C8—C13	118.38 (12)
N1—C1—C3	111.62 (11)	C9—C8—C13	118.67 (12)
N1—C1—C8	119.62 (11)	C8—C9—C10	120.43 (12)
C3—C1—C8	128.74 (12)	C8—C9—H9	120.11
N1—C2—N2	111.21 (11)	C10—C9—H9	119.46
N1—C2—C4	129.56 (12)	C9—C10—C11	120.53 (13)
N2—C2—C4	119.21 (11)	C9—C10—H10	119.74
N2—C3—C1	104.54 (11)	C11—C10—H10	119.73
N2—C3—C14	123.14 (12)	C10—C11—C12	119.65 (13)
C1—C3—C14	132.02 (12)	C10—C11—H11	120.24
C2—C4—C5	118.63 (12)	C12—C11—H11	120.11
C2—C4—H4	121.78	C11—C12—C13	120.19 (12)
C5—C4—H4	119.59	C11—C12—H12	119.70
C4—C5—C6	120.80 (13)	C13—C12—H12	120.11
C4—C5—H5	118.26	C8—C13—C12	120.50 (12)
C6—C5—H5	120.94	C8—C13—H13	120.09
C5—C6—C7	120.66 (12)	C12—C13—H13	119.40
C5—C6—H6	121.49	O1—C14—C3	125.44 (13)
C7—C6—H6	117.85	O1—C14—H14	109.03
N2—C7—C6	118.78 (12)	C3—C14—H14	125.53

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N1i	0.96	2.50	3.4386 (18)	165
C6—H6···O1ii	0.96	2.46	3.1856 (16)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N1i	0.96	2.50	3.4386 (18)	165
C6—H6⋯O1ii	0.96	2.46	3.1856 (16)	133

Symmetry codes: (i) ; (ii) .