Bis(acetophenone oxime) O,O'-methyl-ene ether.

In the mol-ecule of the title compound, C(17)H(18)N(2)O(2), the dihedral angle between the aromatic rings is 74.26 (3)°. The oxime units are oriented at dihedral angles of 7.66 (3) and 33.06 (3)° with respect to the adjacent rings, and they have E configurations about the C=N bonds.

Related literature

For general background on oximes and their varied applications, see: Jones et al. (1961 ▶); Schrauzer & Kohnle (1964 ▶); Hashemi et al. (2006 ▶); Ghiasvand et al. (2004 ▶, 2005 ▶); Kakanejadifard et al. (2007 ▶); Otsuka Pharmaceutical Co Ltd (1981 ▶); Chertanova et al. (1994 ▶).

Experimental

Crystal data

C17H18N2O2

M = 282.33

Monoclinic,

a = 9.875 (2) Å

b = 8.8409 (18) Å

c = 17.290 (4) Å

β = 101.13 (3)°

V = 1481.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 (2) K

0.14 × 0.04 × 0.04 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.988, T max = 0.997

9665 measured reflections

2612 independent reflections

1724 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.097

S = 0.96

2612 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803897X/hk2580sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803897X/hk2580Isup2.hkl

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

C17H18N2O2	F000 = 600
Mr = 282.33	Dx = 1.266 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2756 reflections
a = 9.875 (2) Å	θ = 2.4–27.5º
b = 8.8409 (18) Å	µ = 0.08 mm−1
c = 17.290 (4) Å	T = 113 (2) K
β = 101.13 (3)º	Prism, colorless
V = 1481.1 (6) Å3	0.14 × 0.04 × 0.04 mm
Z = 4

Rigaku Saturn diffractometer	2612 independent reflections
Radiation source: rotating anode	1724 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.105
T = 113(2) K	θmax = 25.0º
ω scans	θmin = 2.2º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	h = −11→11
Tmin = 0.988, Tmax = 0.997	k = −9→10
9665 measured reflections	l = −20→16

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.0345P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097	(Δ/σ)max = 0.001
S = 0.96	Δρmax = 0.23 e Å−3
2612 reflections	Δρmin = −0.19 e Å−3
193 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (2)
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	0.36208 (10)	0.65077 (13)	0.02442 (6)	0.0284 (3)
O2	0.14145 (11)	0.61984 (13)	0.05282 (6)	0.0284 (4)
N1	0.39081 (13)	0.79925 (17)	0.05526 (7)	0.0270 (4)
N2	0.15155 (13)	0.46386 (16)	0.07470 (8)	0.0257 (4)
C1	0.55638 (16)	0.9740 (2)	0.11238 (8)	0.0247 (4)
C2	0.45724 (17)	1.0888 (2)	0.10304 (9)	0.0274 (5)
H2	0.3675	1.0676	0.0774	0.033*
C3	0.48996 (17)	1.2324 (2)	0.13110 (9)	0.0315 (5)
H3	0.4223	1.3070	0.1246	0.038*
C4	0.62333 (18)	1.2665 (2)	0.16904 (9)	0.0357 (5)
H4	0.6457	1.3636	0.1879	0.043*
C5	0.72255 (18)	1.1545 (2)	0.17853 (10)	0.0360 (5)
H5	0.8121	1.1765	0.2041	0.043*
C6	0.69013 (17)	1.0102 (2)	0.15045 (9)	0.0328 (5)
H6	0.7583	0.9362	0.1570	0.039*
C7	0.52021 (16)	0.8199 (2)	0.08160 (9)	0.0251 (4)
C8	0.62975 (17)	0.7028 (2)	0.08213 (10)	0.0362 (5)
H8A	0.5891	0.6128	0.0565	0.054*
H8B	0.6721	0.6797	0.1356	0.054*
H8C	0.6983	0.7408	0.0546	0.054*
C9	0.21947 (16)	0.6427 (2)	−0.00642 (9)	0.0283 (5)
H9A	0.2020	0.5603	−0.0441	0.034*
H9B	0.1899	0.7358	−0.0343	0.034*
C10	0.09103 (15)	0.4381 (2)	0.13271 (9)	0.0231 (4)
C11	0.02188 (17)	0.5564 (2)	0.17390 (10)	0.0329 (5)
H11A	0.0883	0.6006	0.2157	0.049*
H11B	−0.0509	0.5107	0.1954	0.049*
H11C	−0.0159	0.6337	0.1369	0.049*
C12	0.09387 (15)	0.2791 (2)	0.15882 (9)	0.0241 (4)
C13	0.09137 (16)	0.1598 (2)	0.10568 (9)	0.0278 (5)
H13	0.0876	0.1804	0.0526	0.033*
C14	0.09444 (16)	0.0116 (2)	0.13108 (10)	0.0324 (5)
H14	0.0931	−0.0670	0.0952	0.039*
C15	0.09958 (16)	−0.0200 (2)	0.20996 (10)	0.0327 (5)
H15	0.1010	−0.1199	0.2269	0.039*
C16	0.10255 (16)	0.0964 (2)	0.26369 (10)	0.0303 (5)
H16	0.1065	0.0751	0.3167	0.036*
C17	0.09954 (15)	0.2444 (2)	0.23818 (9)	0.0265 (5)
H17	0.1013	0.3224	0.2744	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0275 (7)	0.0271 (9)	0.0310 (7)	0.0022 (6)	0.0069 (5)	−0.0017 (5)
O2	0.0292 (7)	0.0262 (9)	0.0310 (7)	0.0010 (6)	0.0085 (5)	0.0017 (5)
N1	0.0287 (8)	0.0268 (10)	0.0262 (8)	0.0008 (7)	0.0071 (6)	0.0000 (6)
N2	0.0248 (8)	0.0211 (10)	0.0305 (8)	−0.0004 (7)	0.0031 (6)	0.0003 (7)
C1	0.0231 (9)	0.0314 (13)	0.0209 (9)	0.0014 (9)	0.0073 (7)	0.0047 (8)
C2	0.0244 (9)	0.0333 (13)	0.0246 (9)	−0.0004 (9)	0.0050 (7)	−0.0009 (8)
C3	0.0325 (10)	0.0335 (14)	0.0296 (10)	0.0025 (9)	0.0085 (8)	0.0005 (8)
C4	0.0412 (12)	0.0374 (14)	0.0286 (10)	−0.0098 (10)	0.0073 (8)	0.0012 (9)
C5	0.0265 (10)	0.0471 (16)	0.0328 (11)	−0.0084 (10)	0.0018 (8)	0.0047 (9)
C6	0.0252 (10)	0.0420 (15)	0.0317 (10)	0.0013 (9)	0.0070 (7)	0.0069 (9)
C7	0.0250 (9)	0.0308 (12)	0.0205 (9)	0.0053 (8)	0.0068 (7)	0.0052 (8)
C8	0.0293 (10)	0.0370 (14)	0.0416 (11)	0.0072 (9)	0.0051 (8)	0.0005 (9)
C9	0.0278 (10)	0.0332 (13)	0.0236 (10)	−0.0026 (8)	0.0044 (8)	0.0017 (8)
C10	0.0173 (9)	0.0276 (12)	0.0237 (9)	−0.0008 (8)	0.0024 (7)	−0.0040 (8)
C11	0.0334 (10)	0.0299 (13)	0.0369 (10)	0.0031 (9)	0.0100 (8)	−0.0027 (8)
C12	0.0167 (9)	0.0258 (12)	0.0294 (10)	−0.0002 (8)	0.0038 (7)	−0.0014 (8)
C13	0.0255 (10)	0.0300 (14)	0.0288 (10)	−0.0012 (9)	0.0075 (7)	−0.0028 (8)
C14	0.0301 (10)	0.0265 (13)	0.0411 (11)	0.0014 (9)	0.0082 (8)	−0.0058 (9)
C15	0.0252 (10)	0.0278 (13)	0.0440 (11)	0.0011 (9)	0.0037 (8)	0.0050 (9)
C16	0.0254 (10)	0.0332 (14)	0.0310 (10)	−0.0004 (9)	0.0023 (8)	0.0044 (9)
C17	0.0203 (9)	0.0278 (13)	0.0309 (10)	−0.0008 (8)	0.0041 (7)	−0.0059 (8)

O1—C9	1.4081 (17)	C8—H8B	0.9600
O1—N1	1.4246 (17)	C8—H8C	0.9600
O2—C9	1.4100 (19)	C9—H9A	0.9700
O2—N2	1.4283 (17)	C9—H9B	0.9700
N1—C7	1.2842 (19)	C10—C12	1.476 (2)
N2—C10	1.283 (2)	C10—C11	1.502 (2)
C1—C6	1.394 (2)	C11—H11A	0.9600
C1—C2	1.397 (2)	C11—H11B	0.9600
C1—C7	1.481 (2)	C11—H11C	0.9600
C2—C3	1.375 (2)	C12—C13	1.396 (2)
C2—H2	0.9300	C12—C17	1.397 (2)
C3—C4	1.386 (2)	C13—C14	1.381 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.380 (2)	C14—C15	1.383 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.381 (2)	C15—C16	1.383 (2)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.379 (2)
C7—C8	1.496 (2)	C16—H16	0.9300
C8—H8A	0.9600	C17—H17	0.9300
C9—O1—N1	107.51 (12)	O1—C9—H9A	109.1
C9—O2—N2	108.10 (12)	O2—C9—H9A	109.1
C7—N1—O1	112.12 (13)	O1—C9—H9B	109.1
C10—N2—O2	111.03 (14)	O2—C9—H9B	109.1
C6—C1—C2	117.83 (17)	H9A—C9—H9B	107.9
C6—C1—C7	121.41 (15)	N2—C10—C12	115.07 (16)
C2—C1—C7	120.75 (14)	N2—C10—C11	124.78 (17)
C3—C2—C1	121.18 (15)	C12—C10—C11	120.15 (16)
C3—C2—H2	119.4	C10—C11—H11A	109.5
C1—C2—H2	119.4	C10—C11—H11B	109.5
C2—C3—C4	120.31 (17)	H11A—C11—H11B	109.5
C2—C3—H3	119.8	C10—C11—H11C	109.5
C4—C3—H3	119.8	H11A—C11—H11C	109.5
C5—C4—C3	119.23 (18)	H11B—C11—H11C	109.5
C5—C4—H4	120.4	C13—C12—C17	118.25 (17)
C3—C4—H4	120.4	C13—C12—C10	121.45 (16)
C4—C5—C6	120.65 (16)	C17—C12—C10	120.30 (15)
C4—C5—H5	119.7	C14—C13—C12	120.74 (16)
C6—C5—H5	119.7	C14—C13—H13	119.6
C5—C6—C1	120.80 (17)	C12—C13—H13	119.6
C5—C6—H6	119.6	C13—C14—C15	119.97 (17)
C1—C6—H6	119.6	C13—C14—H14	120.0
N1—C7—C1	114.38 (15)	C15—C14—H14	120.0
N1—C7—C8	124.93 (16)	C16—C15—C14	120.26 (18)
C1—C7—C8	120.69 (14)	C16—C15—H15	119.9
C7—C8—H8A	109.5	C14—C15—H15	119.9
C7—C8—H8B	109.5	C17—C16—C15	119.67 (17)
H8A—C8—H8B	109.5	C17—C16—H16	120.2
C7—C8—H8C	109.5	C15—C16—H16	120.2
H8A—C8—H8C	109.5	C16—C17—C12	121.11 (16)
H8B—C8—H8C	109.5	C16—C17—H17	119.4
O1—C9—O2	112.27 (12)	C12—C17—H17	119.4
C9—O1—N1—C7	−176.97 (13)	N1—O1—C9—O2	−79.77 (15)
C9—O2—N2—C10	175.14 (11)	N2—O2—C9—O1	−78.02 (14)
C6—C1—C2—C3	−0.6 (2)	O2—N2—C10—C12	179.02 (10)
C7—C1—C2—C3	−179.71 (15)	O2—N2—C10—C11	−1.56 (19)
C1—C2—C3—C4	0.4 (3)	N2—C10—C12—C13	−32.7 (2)
C2—C3—C4—C5	−0.2 (3)	C11—C10—C12—C13	147.83 (15)
C3—C4—C5—C6	0.2 (3)	N2—C10—C12—C17	147.12 (15)
C4—C5—C6—C1	−0.4 (3)	C11—C10—C12—C17	−32.3 (2)
C2—C1—C6—C5	0.6 (2)	C17—C12—C13—C14	0.0 (2)
C7—C1—C6—C5	179.70 (16)	C10—C12—C13—C14	179.83 (14)
O1—N1—C7—C1	178.38 (12)	C12—C13—C14—C15	0.2 (2)
O1—N1—C7—C8	−1.2 (2)	C13—C14—C15—C16	−0.4 (2)
C6—C1—C7—N1	173.26 (15)	C14—C15—C16—C17	0.4 (2)
C2—C1—C7—N1	−7.7 (2)	C15—C16—C17—C12	−0.2 (2)
C6—C1—C7—C8	−7.1 (2)	C13—C12—C17—C16	0.0 (2)
C2—C1—C7—C8	171.95 (15)	C10—C12—C17—C16	−179.87 (14)