Crystal structure of (1Z,2E)-cinnamaldehyde oxime.

The title compound, C9H9NO, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The conformation of the two mol-ecules differs slightly with the phenyl ring in mol-ecule A, forming a dihedral angle of 15.38 (12)° with the oxime group (O-N=C), compared to the corresponding angle of 26.29 (11)° in mol-ecule B. In the crystal, the A and B mol-ecules are linked head-to-head by O-H⋯N hydrogen bonds, forming -A-B-A-B- zigzag chains along [010]. Within the chains and between neighbouring chains there are C-H⋯π inter-actions present, forming a three-dimensional structure.

Related literature

For the other methods of preparation of the title compound, see: Mirjafari et al. (2011 ▸); Kitahara et al. (2008 ▸). For the uses of a such compound, see: Narsaiah & Nagaiah (2004 ▸); Jasem et al. (2014 ▸); Garton et al. (2010 ▸); Patil et al. (2012 ▸); Kaur et al. (2006 ▸); Boruah & Konwar (2012 ▸).

Experimental

Crystal data

C9H9NO

M = 147.17

Orthorhombic,

a = 10.231 (5) Å

b = 7.584 (3) Å

c = 41.816 (18) Å

V = 3245 (2) Å3

Z = 16

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.2 × 0.2 × 0.1 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.666, T max = 0.746

34431 measured reflections

3944 independent reflections

3724 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.10

3944 reflections

207 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015023853/su5260sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023853/su5260Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015023853/su5260Isup3.cml

Click here for additional data file.

A B . DOI: 10.1107/S2056989015023853/su5260fig1.tif

A view of the mol­ecular structure of the two independent mol­ecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015023853/su5260fig2.tif

A partial view along the a axis of the crystal packing of the title compound. The O—H⋯N hydrogen bonds, and the C—H⋯π contacts between adjacent mol­ecules are shown as dashed lines (see Table 1).

Click here for additional data file.

b b . DOI: 10.1107/S2056989015023853/su5260fig3.tif

A view along the b axis of three stacked mol­ecular motifs made of A (blue) and B (green) inter­connected mol­ecules forming chains along the b axis. The hydrogen bonds and C—H⋯π inter­actions are shown as dashed lines (see Table 1).

CCDC reference: 1441984

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H9NO	Dx = 1.205 Mg m−3
Mr = 147.17	Melting point: 348 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 10.231 (5) Å	Cell parameters from 9623 reflections
b = 7.584 (3) Å	θ = 2.2–28.4°
c = 41.816 (18) Å	µ = 0.08 mm−1
V = 3245 (2) Å3	T = 100 K
Z = 16	Block, colourless
F(000) = 1248	0.2 × 0.2 × 0.1 mm

Bruker APEXII CCD diffractometer	3724 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.022
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 28.6°, θmin = 1.0°
Tmin = 0.666, Tmax = 0.746	h = −13→13
34431 measured reflections	k = −10→10
3944 independent reflections	l = −55→53

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0445P)2 + 2.1543P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3944 reflections	Δρmax = 0.45 e Å−3
207 parameters	Δρmin = −0.19 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.

	x	y	z	Uiso*/Ueq
O1B	0.27939 (9)	0.14918 (13)	0.83349 (2)	0.0214 (2)
O1A	0.57897 (9)	0.36622 (12)	0.60376 (2)	0.0210 (2)
N1A	0.65418 (10)	0.21056 (14)	0.60658 (2)	0.0172 (2)
N1B	0.37727 (11)	0.02042 (14)	0.83755 (2)	0.0189 (2)
C9A	0.66426 (11)	0.12592 (16)	0.57973 (3)	0.0162 (2)
H9A	0.7096	0.0167	0.5804	0.019*
C7A	0.65649 (11)	0.10018 (15)	0.52143 (3)	0.0146 (2)
H7A	0.7135	0.0024	0.5242	0.017*
C1A	0.62383 (11)	0.14952 (15)	0.48805 (3)	0.0137 (2)
C6A	0.52038 (11)	0.26618 (15)	0.48030 (3)	0.0152 (2)
H6A	0.4665	0.3124	0.4968	0.018*
C2B	0.50012 (12)	−0.04774 (16)	0.69394 (3)	0.0171 (2)
H2B	0.5770	−0.1114	0.6993	0.021*
C5A	0.49730 (12)	0.31367 (16)	0.44838 (3)	0.0182 (2)
H5A	0.4278	0.3920	0.4434	0.022*
C7B	0.44406 (12)	−0.04211 (15)	0.75192 (3)	0.0167 (2)
H7B	0.5154	−0.1202	0.7552	0.020*
C2A	0.70079 (12)	0.08011 (17)	0.46297 (3)	0.0189 (2)
H2A	0.7689	−0.0008	0.4678	0.023*
C8A	0.61346 (11)	0.18013 (15)	0.54843 (3)	0.0152 (2)
H8A	0.5502	0.2716	0.5471	0.018*
C1B	0.41218 (11)	0.00325 (15)	0.71837 (3)	0.0153 (2)
C3B	0.47534 (13)	−0.00548 (17)	0.66187 (3)	0.0202 (3)
H3B	0.5352	−0.0408	0.6457	0.024*
C5B	0.27317 (13)	0.13917 (17)	0.67760 (3)	0.0224 (3)
H5B	0.1963	0.2023	0.6720	0.027*
C6B	0.29760 (12)	0.09644 (16)	0.70966 (3)	0.0188 (2)
H6B	0.2368	0.1303	0.7257	0.023*
C4B	0.36242 (14)	0.08882 (17)	0.65358 (3)	0.0228 (3)
H4B	0.3461	0.1186	0.6319	0.027*
C8B	0.38138 (12)	0.01692 (16)	0.77854 (3)	0.0170 (2)
H8B	0.3088	0.0942	0.7763	0.020*
C9B	0.42381 (13)	−0.03653 (16)	0.81057 (3)	0.0191 (2)
H9B	0.4921	−0.1212	0.8117	0.023*
C4A	0.57625 (13)	0.24623 (18)	0.42372 (3)	0.0220 (3)
H4A	0.5607	0.2799	0.4022	0.026*
C3A	0.67797 (14)	0.12902 (18)	0.43106 (3)	0.0235 (3)
H3A	0.7314	0.0828	0.4145	0.028*
H1B	0.248 (2)	0.163 (2)	0.8539 (4)	0.039 (5)*
H1A	0.588 (2)	0.415 (3)	0.6235 (5)	0.048 (6)*

	U11	U22	U33	U12	U13	U23
O1B	0.0216 (4)	0.0283 (5)	0.0144 (4)	0.0041 (4)	0.0037 (3)	0.0011 (3)
O1A	0.0301 (5)	0.0197 (4)	0.0131 (4)	0.0029 (4)	−0.0024 (3)	−0.0010 (3)
N1A	0.0181 (5)	0.0191 (5)	0.0144 (5)	−0.0022 (4)	−0.0008 (4)	0.0040 (4)
N1B	0.0237 (5)	0.0183 (5)	0.0146 (5)	−0.0013 (4)	−0.0001 (4)	0.0023 (4)
C9A	0.0169 (5)	0.0174 (5)	0.0141 (5)	−0.0026 (4)	−0.0012 (4)	0.0033 (4)
C7A	0.0143 (5)	0.0136 (5)	0.0159 (5)	−0.0011 (4)	−0.0030 (4)	0.0012 (4)
C1A	0.0158 (5)	0.0118 (5)	0.0134 (5)	−0.0026 (4)	−0.0024 (4)	−0.0012 (4)
C6A	0.0148 (5)	0.0147 (5)	0.0160 (5)	−0.0010 (4)	−0.0008 (4)	−0.0011 (4)
C2B	0.0167 (5)	0.0167 (5)	0.0178 (5)	−0.0018 (4)	0.0025 (4)	−0.0009 (4)
C5A	0.0179 (5)	0.0171 (5)	0.0195 (6)	−0.0008 (4)	−0.0054 (4)	0.0022 (4)
C7B	0.0196 (5)	0.0142 (5)	0.0164 (5)	0.0014 (4)	0.0010 (4)	0.0006 (4)
C2A	0.0206 (6)	0.0189 (6)	0.0172 (6)	0.0051 (5)	−0.0019 (4)	−0.0028 (4)
C8A	0.0164 (5)	0.0151 (5)	0.0141 (5)	−0.0020 (4)	−0.0023 (4)	0.0015 (4)
C1B	0.0189 (5)	0.0125 (5)	0.0144 (5)	−0.0018 (4)	0.0019 (4)	−0.0005 (4)
C3B	0.0254 (6)	0.0203 (6)	0.0149 (5)	−0.0065 (5)	0.0053 (5)	−0.0020 (4)
C5B	0.0265 (7)	0.0189 (6)	0.0218 (6)	0.0021 (5)	−0.0048 (5)	0.0013 (5)
C6B	0.0211 (6)	0.0179 (6)	0.0175 (6)	0.0020 (5)	0.0019 (4)	−0.0010 (4)
C4B	0.0324 (7)	0.0207 (6)	0.0152 (5)	−0.0065 (5)	−0.0032 (5)	0.0023 (5)
C8B	0.0206 (5)	0.0157 (5)	0.0146 (5)	−0.0005 (4)	0.0015 (4)	0.0009 (4)
C9B	0.0239 (6)	0.0171 (6)	0.0162 (5)	0.0001 (5)	0.0007 (4)	0.0022 (4)
C4A	0.0290 (6)	0.0236 (6)	0.0133 (5)	−0.0014 (5)	−0.0052 (5)	0.0011 (5)
C3A	0.0299 (7)	0.0270 (7)	0.0137 (5)	0.0033 (5)	0.0015 (5)	−0.0048 (5)

C1A—C2A	1.4133 (17)	C6A—H6A	0.9500
C1A—C6A	1.4171 (16)	C6B—H6B	0.9500
C1B—C6B	1.4166 (17)	C7A—C8A	1.3548 (17)
C2A—C3A	1.4043 (18)	C7A—C1A	1.4834 (16)
C2A—H2A	0.9500	C7A—H7A	0.9500
C2B—C3B	1.4020 (17)	C7B—C8B	1.3606 (17)
C2B—C1B	1.4152 (16)	C7B—C1B	1.4806 (17)
C2B—H2B	0.9500	C7B—H7B	0.9500
C3A—H3A	0.9500	C8A—H8A	0.9500
C3B—C4B	1.402 (2)	C8B—C9B	1.4649 (17)
C3B—H3B	0.9500	C8B—H8B	0.9500
C4A—C3A	1.4027 (19)	C9A—C8A	1.4671 (16)
C4A—H4A	0.9500	C9A—H9A	0.9500
C4B—H4B	0.9500	C9B—H9B	0.9500
C5A—C4A	1.4063 (19)	N1A—C9A	1.2977 (16)
C5A—H5A	0.9500	N1B—C9B	1.2985 (16)
C5B—C4B	1.4100 (19)	O1A—H1A	0.91 (2)
C5B—C6B	1.4017 (18)	O1A—N1A	1.4141 (14)
C5B—H5B	0.9500	O1B—H1B	0.917 (19)
C6A—C5A	1.4026 (17)	O1B—N1B	1.4090 (14)
C1A—C2A—H2A	119.5	C5B—C4B—H4B	120.1
C1A—C6A—H6A	119.9	C5B—C6B—H6B	119.7
C1A—C7A—H7A	116.6	C5B—C6B—C1B	120.60 (11)
C1B—C6B—H6B	119.7	C6A—C5A—C4A	120.52 (11)
C1B—C7B—H7B	116.7	C6A—C5A—H5A	119.7
C1B—C2B—H2B	119.6	C6A—C1A—C7A	122.75 (10)
C2A—C3A—H3A	120.0	C6B—C5B—C4B	120.20 (12)
C2A—C1A—C6A	118.62 (11)	C6B—C5B—H5B	119.9
C2A—C1A—C7A	118.62 (11)	C6B—C1B—C7B	122.82 (10)
C2B—C3B—C4B	120.13 (11)	C7A—C8A—H8A	119.9
C2B—C3B—H3B	119.9	C7A—C8A—C9A	120.18 (11)
C2B—C1B—C6B	118.47 (11)	C7B—C8B—C9B	121.15 (12)
C2B—C1B—C7B	118.71 (11)	C7B—C8B—H8B	119.4
C3A—C4A—H4A	120.1	C8A—C7A—C1A	126.72 (11)
C3A—C4A—C5A	119.75 (11)	C8A—C7A—H7A	116.6
C3A—C2A—H2A	119.5	C8A—C9A—H9A	116.4
C3A—C2A—C1A	120.94 (11)	C8B—C9B—H9B	116.8
C3B—C4B—H4B	120.1	C8B—C7B—C1B	126.51 (11)
C3B—C4B—C5B	119.72 (12)	C8B—C7B—H7B	116.7
C3B—C2B—C1B	120.87 (12)	C9A—C8A—H8A	119.9
C3B—C2B—H2B	119.6	C9A—N1A—O1A	112.58 (9)
C4A—C3A—H3A	120.0	C9B—C8B—H8B	119.4
C4A—C3A—C2A	119.91 (11)	C9B—N1B—O1B	112.73 (10)
C4A—C5A—H5A	119.7	N1A—C9A—C8A	127.25 (11)
C4B—C5B—H5B	119.9	N1A—C9A—H9A	116.4
C4B—C3B—H3B	119.9	N1A—O1A—H1A	102.2 (13)
C5A—C4A—H4A	120.1	N1B—C9B—H9B	116.8
C5A—C6A—H6A	119.9	N1B—C9B—C8B	126.41 (12)
C5A—C6A—C1A	120.24 (11)	N1B—O1B—H1B	102.2 (12)
C1A—C2A—C3A—C4A	−1.0 (2)	C6A—C1A—C2A—C3A	1.73 (18)
C1A—C6A—C5A—C4A	0.04 (18)	C6B—C5B—C4B—C3B	0.50 (19)
C1A—C7A—C8A—C9A	−174.32 (11)	C7A—C1A—C2A—C3A	−177.00 (11)
C1B—C7B—C8B—C9B	−179.24 (11)	C7A—C1A—C6A—C5A	177.43 (11)
C1B—C2B—C3B—C4B	0.13 (18)	C7B—C8B—C9B—N1B	175.07 (12)
C2A—C1A—C6A—C5A	−1.24 (17)	C7B—C1B—C6B—C5B	178.75 (12)
C2B—C3B—C4B—C5B	−0.73 (19)	C8A—C7A—C1A—C2A	165.01 (12)
C2B—C1B—C6B—C5B	−0.92 (18)	C8A—C7A—C1A—C6A	−13.66 (18)
C3B—C2B—C1B—C6B	0.69 (18)	C8B—C7B—C1B—C6B	−9.56 (19)
C3B—C2B—C1B—C7B	−179.00 (11)	C8B—C7B—C1B—C2B	170.11 (12)
C4B—C5B—C6B—C1B	0.34 (19)	N1A—C9A—C8A—C7A	164.78 (12)
C5A—C4A—C3A—C2A	−0.2 (2)	O1A—N1A—C9A—C8A	3.45 (17)
C6A—C5A—C4A—C3A	0.71 (19)	O1B—N1B—C9B—C8B	−1.80 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N1Bi	0.91 (2)	1.85 (2)	2.755 (2)	174 (2)
O1B—H1B···N1Aii	0.92 (2)	1.95 (2)	2.853 (2)	170 (2)
C2A—H2A···Cg1iii	0.95	2.70	3.563 (2)	151
C5B—H5B···Cg2iv	0.95	2.80	3.508 (2)	132
C9B—H9B···Cg2v	0.95	2.82	3.717 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C1A–C6A and C1B–C6B, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯N1B i	0.91 (2)	1.85 (2)	2.755 (2)	174 (2)
O1B—H1B⋯N1A ii	0.92 (2)	1.95 (2)	2.853 (2)	170 (2)
C2A—H2A⋯Cg1iii	0.95	2.70	3.563 (2)	151
C5B—H5B⋯Cg2iv	0.95	2.80	3.508 (2)	132
C9B—H9B⋯Cg2v	0.95	2.82	3.717 (2)	159

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