N-[(E)-3,4-Dimeth-oxy-benzyl-idene]-2,3-dimethyl-aniline.

In the title compound, C(17)H(19)NO(2), the aromatic rings are oriented at a dihedral angle of 59.27 (12)°. In the crystal, inversion dimers linked by pairs of weak C-H⋯O inter-actions generate R(2) (2)(12) loops.

Related literature

For related structures, see: Sarfraz et al. (2010 ▶); Tahir et al. (2010 ▶); Tariq et al. (2010 ▶).

Experimental

Crystal data

C17H19NO2

M = 269.33

Triclinic,

a = 7.0144 (4) Å

b = 7.4488 (4) Å

c = 15.6202 (8) Å

α = 81.987 (2)°

β = 81.009 (3)°

γ = 73.527 (2)°

V = 769.12 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.34 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.972, T max = 0.983

8993 measured reflections

3688 independent reflections

2028 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.211

S = 1.08

3688 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032892/hb6358sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032892/hb6358Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032892/hb6358Isup3.cml

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

C17H19NO2	Z = 2
Mr = 269.33	F(000) = 288
Triclinic, P1	Dx = 1.163 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0144 (4) Å	Cell parameters from 2028 reflections
b = 7.4488 (4) Å	θ = 2.7–28.4°
c = 15.6202 (8) Å	µ = 0.08 mm−1
α = 81.987 (2)°	T = 296 K
β = 81.009 (3)°	Prism, colorless
γ = 73.527 (2)°	0.34 × 0.25 × 0.22 mm
V = 769.12 (7) Å3

Bruker Kappa APEXII CCD diffractometer	3688 independent reflections
Radiation source: fine-focus sealed tube	2028 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 7.50 pixels mm-1	θmax = 28.4°, θmin = 2.7°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.972, Tmax = 0.983	l = −20→20
8993 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0973P)2 + 0.0736P] where P = (Fo2 + 2Fc2)/3
3688 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.4243 (2)	1.3278 (2)	0.06049 (11)	0.1032 (6)
O2	0.0678 (3)	1.5334 (3)	0.09093 (12)	0.1237 (7)
N1	0.4479 (2)	0.7156 (3)	0.26807 (10)	0.0781 (6)
C1	0.4907 (3)	0.5385 (3)	0.31797 (12)	0.0724 (7)
C2	0.6399 (3)	0.4985 (2)	0.37272 (11)	0.0653 (6)
C3	0.6892 (3)	0.3227 (3)	0.42177 (13)	0.0801 (7)
C4	0.5942 (5)	0.1908 (3)	0.41376 (19)	0.1067 (10)
C5	0.4515 (5)	0.2251 (4)	0.3599 (2)	0.1191 (11)
C6	0.3959 (4)	0.4001 (4)	0.31104 (18)	0.1058 (10)
C7	0.7449 (3)	0.6439 (3)	0.38007 (15)	0.0814 (7)
C8	0.8467 (4)	0.2768 (3)	0.48259 (17)	0.1107 (10)
C9	0.2673 (3)	0.8109 (4)	0.26475 (13)	0.0873 (8)
C10	0.2098 (3)	0.9939 (4)	0.21549 (13)	0.0872 (8)
C11	0.3509 (3)	1.0665 (3)	0.15843 (12)	0.0804 (7)
C12	0.2991 (3)	1.2443 (3)	0.11668 (13)	0.0845 (7)
C13	0.1014 (3)	1.3574 (4)	0.13272 (14)	0.0982 (9)
C14	−0.0383 (3)	1.2866 (5)	0.18777 (16)	0.1098 (12)
C15	0.0153 (3)	1.1059 (5)	0.22878 (16)	0.1091 (12)
C16	0.6230 (3)	1.2208 (3)	0.03706 (18)	0.1017 (9)
C17	−0.1297 (4)	1.6586 (5)	0.1040 (2)	0.1511 (14)
H4	0.62832	0.07416	0.44610	0.1282*
H5	0.38993	0.13205	0.35542	0.1429*
H6	0.29718	0.42404	0.27438	0.1267*
H7A	0.71156	0.74586	0.33535	0.1221*
H7B	0.88706	0.58857	0.37339	0.1221*
H7C	0.70333	0.69060	0.43618	0.1221*
H8A	0.84583	0.15970	0.51705	0.1659*
H8B	0.81876	0.37504	0.52020	0.1659*
H8C	0.97589	0.26637	0.44934	0.1659*
H9	0.16648	0.76071	0.29555	0.1047*
H11	0.48208	0.99265	0.14874	0.0964*
H14	−0.16955	1.36030	0.19753	0.1317*
H15	−0.08069	1.05903	0.26580	0.1308*
H16A	0.69124	1.18297	0.08799	0.1523*
H16B	0.69194	1.29576	−0.00456	0.1523*
H16C	0.62060	1.11121	0.01184	0.1523*
H17A	−0.22229	1.60982	0.08122	0.2265*
H17B	−0.12956	1.78039	0.07430	0.2265*
H17C	−0.16937	1.66912	0.16514	0.2265*

	U11	U22	U33	U12	U13	U23
O1	0.0793 (9)	0.1041 (11)	0.0950 (11)	0.0173 (8)	−0.0053 (8)	0.0011 (8)
O2	0.0955 (11)	0.1343 (14)	0.0975 (12)	0.0434 (10)	−0.0131 (9)	−0.0186 (10)
N1	0.0689 (10)	0.1016 (12)	0.0657 (10)	−0.0269 (9)	−0.0016 (7)	−0.0135 (8)
C1	0.0726 (11)	0.0870 (13)	0.0648 (10)	−0.0362 (10)	0.0107 (9)	−0.0220 (9)
C2	0.0683 (10)	0.0677 (11)	0.0609 (10)	−0.0251 (8)	0.0103 (8)	−0.0157 (8)
C3	0.0919 (13)	0.0699 (12)	0.0725 (12)	−0.0256 (10)	0.0236 (10)	−0.0164 (9)
C4	0.133 (2)	0.0838 (15)	0.1044 (19)	−0.0482 (15)	0.0309 (16)	−0.0238 (13)
C5	0.144 (2)	0.1027 (19)	0.133 (2)	−0.0808 (18)	0.034 (2)	−0.0442 (18)
C6	0.1058 (17)	0.139 (2)	0.0977 (17)	−0.0668 (16)	0.0115 (13)	−0.0523 (16)
C7	0.0819 (12)	0.0803 (12)	0.0893 (14)	−0.0328 (10)	−0.0139 (10)	−0.0060 (10)
C8	0.124 (2)	0.0967 (16)	0.0917 (17)	−0.0090 (15)	−0.0065 (15)	0.0061 (13)
C9	0.0686 (12)	0.1318 (18)	0.0640 (12)	−0.0304 (12)	−0.0026 (9)	−0.0174 (12)
C10	0.0633 (11)	0.1337 (19)	0.0587 (11)	−0.0106 (11)	−0.0090 (9)	−0.0217 (12)
C11	0.0590 (10)	0.1120 (16)	0.0585 (10)	0.0010 (10)	−0.0108 (8)	−0.0156 (10)
C12	0.0670 (11)	0.1122 (16)	0.0570 (11)	0.0084 (11)	−0.0100 (9)	−0.0159 (10)
C13	0.0765 (13)	0.130 (2)	0.0626 (12)	0.0260 (13)	−0.0180 (10)	−0.0259 (12)
C14	0.0621 (12)	0.167 (3)	0.0755 (14)	0.0215 (14)	−0.0105 (11)	−0.0365 (15)
C15	0.0625 (12)	0.178 (3)	0.0730 (14)	−0.0054 (15)	−0.0046 (10)	−0.0264 (16)
C16	0.0696 (12)	0.0984 (16)	0.122 (2)	−0.0017 (11)	−0.0060 (12)	−0.0103 (14)
C17	0.114 (2)	0.163 (3)	0.118 (2)	0.0679 (19)	−0.0177 (17)	−0.035 (2)

O1—C12	1.358 (3)	C14—C15	1.383 (5)
O1—C16	1.416 (3)	C4—H4	0.9300
O2—C13	1.355 (3)	C5—H5	0.9300
O2—C17	1.436 (4)	C6—H6	0.9300
N1—C1	1.414 (3)	C7—H7A	0.9600
N1—C9	1.270 (3)	C7—H7B	0.9600
C1—C2	1.396 (3)	C7—H7C	0.9600
C1—C6	1.400 (4)	C8—H8A	0.9600
C2—C3	1.403 (3)	C8—H8B	0.9600
C2—C7	1.497 (3)	C8—H8C	0.9600
C3—C4	1.363 (4)	C9—H9	0.9300
C3—C8	1.504 (4)	C11—H11	0.9300
C4—C5	1.354 (5)	C14—H14	0.9300
C5—C6	1.400 (4)	C15—H15	0.9300
C9—C10	1.451 (4)	C16—H16A	0.9600
C10—C11	1.400 (3)	C16—H16B	0.9600
C10—C15	1.384 (4)	C16—H16C	0.9600
C11—C12	1.368 (3)	C17—H17A	0.9600
C12—C13	1.408 (3)	C17—H17B	0.9600
C13—C14	1.372 (3)	C17—H17C	0.9600
C12—O1—C16	118.63 (17)	C5—C6—H6	120.00
C13—O2—C17	118.4 (2)	C2—C7—H7A	109.00
C1—N1—C9	119.83 (19)	C2—C7—H7B	109.00
N1—C1—C2	118.28 (18)	C2—C7—H7C	109.00
N1—C1—C6	122.3 (2)	H7A—C7—H7B	109.00
C2—C1—C6	119.3 (2)	H7A—C7—H7C	109.00
C1—C2—C3	119.81 (18)	H7B—C7—H7C	109.00
C1—C2—C7	120.07 (16)	C3—C8—H8A	109.00
C3—C2—C7	120.11 (18)	C3—C8—H8B	109.00
C2—C3—C4	119.6 (2)	C3—C8—H8C	109.00
C2—C3—C8	121.02 (19)	H8A—C8—H8B	109.00
C4—C3—C8	119.4 (2)	H8A—C8—H8C	109.00
C3—C4—C5	121.7 (2)	H8B—C8—H8C	109.00
C4—C5—C6	120.3 (3)	N1—C9—H9	118.00
C1—C6—C5	119.3 (3)	C10—C9—H9	118.00
N1—C9—C10	123.5 (2)	C10—C11—H11	119.00
C9—C10—C11	121.3 (2)	C12—C11—H11	119.00
C9—C10—C15	120.1 (2)	C13—C14—H14	120.00
C11—C10—C15	118.5 (2)	C15—C14—H14	120.00
C10—C11—C12	121.1 (2)	C10—C15—H15	120.00
O1—C12—C11	125.7 (2)	C14—C15—H15	120.00
O1—C12—C13	114.90 (19)	O1—C16—H16A	109.00
C11—C12—C13	119.4 (2)	O1—C16—H16B	109.00
O2—C13—C12	114.7 (2)	O1—C16—H16C	109.00
O2—C13—C14	125.5 (3)	H16A—C16—H16B	109.00
C12—C13—C14	119.8 (3)	H16A—C16—H16C	109.00
C13—C14—C15	120.2 (3)	H16B—C16—H16C	109.00
C10—C15—C14	120.9 (2)	O2—C17—H17A	109.00
C3—C4—H4	119.00	O2—C17—H17B	109.00
C5—C4—H4	119.00	O2—C17—H17C	109.00
C4—C5—H5	120.00	H17A—C17—H17B	109.00
C6—C5—H5	120.00	H17A—C17—H17C	109.00
C1—C6—H6	120.00	H17B—C17—H17C	110.00
C16—O1—C12—C11	4.7 (3)	C8—C3—C4—C5	−180.0 (3)
C16—O1—C12—C13	−176.7 (2)	C3—C4—C5—C6	−0.6 (5)
C17—O2—C13—C12	−179.7 (2)	C4—C5—C6—C1	0.5 (4)
C17—O2—C13—C14	−0.3 (4)	N1—C9—C10—C11	8.8 (4)
C9—N1—C1—C2	−133.8 (2)	N1—C9—C10—C15	−166.8 (2)
C9—N1—C1—C6	49.3 (3)	C9—C10—C11—C12	−175.4 (2)
C1—N1—C9—C10	179.8 (2)	C15—C10—C11—C12	0.2 (3)
N1—C1—C2—C3	−178.66 (18)	C9—C10—C15—C14	174.7 (2)
N1—C1—C2—C7	2.3 (3)	C11—C10—C15—C14	−1.0 (4)
C6—C1—C2—C3	−1.7 (3)	C10—C11—C12—O1	179.8 (2)
C6—C1—C2—C7	179.2 (2)	C10—C11—C12—C13	1.2 (3)
N1—C1—C6—C5	177.5 (2)	O1—C12—C13—O2	−1.3 (3)
C2—C1—C6—C5	0.6 (4)	O1—C12—C13—C14	179.3 (2)
C1—C2—C3—C4	1.7 (3)	C11—C12—C13—O2	177.4 (2)
C1—C2—C3—C8	−178.9 (2)	C11—C12—C13—C14	−2.0 (3)
C7—C2—C3—C4	−179.3 (2)	O2—C13—C14—C15	−178.1 (2)
C7—C2—C3—C8	0.2 (3)	C12—C13—C14—C15	1.2 (4)
C2—C3—C4—C5	−0.5 (4)	C13—C14—C15—C10	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O2i	0.96	2.51	3.454 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O2i	0.96	2.51	3.454 (3)	167

Symmetry code: (i) .