(E)-N-(2,4-Dimeth-oxy-benzyl-idene)-4-ethoxyaniline.

In the title compound, C(17)H(19)NO(3), the mol-ecule has an E configuration with respect to the C=N bond and the dihedral angle between the aromatic rings is 56.07 (5)°. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds occur. The dimers are linked by weak C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For related structures and background references, see: Khalaji et al. (2010a ▶,b ▶).

Experimental

Crystal data

C17H19NO3

M = 285.3

Monoclinic,

a = 8.4536 (1) Å

b = 9.6531 (2) Å

c = 18.0561 (3) Å

β = 90.9091 (10)°

V = 1473.25 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 120 K

0.50 × 0.12 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶), T min = 0.714, T max = 1.000

18522 measured reflections

2543 independent reflections

2259 reflections with I > 3σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.098

S = 1.98

2543 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2007 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041759/hb5685sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041759/hb5685Isup2.hkl

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

C17H19NO3	F(000) = 608
Mr = 285.3	Dx = 1.286 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 13339 reflections
a = 8.4536 (1) Å	θ = 4.6–66.4°
b = 9.6531 (2) Å	µ = 0.71 mm−1
c = 18.0561 (3) Å	T = 120 K
β = 90.9091 (10)°	Prism, colourless
V = 1473.25 (4) Å3	0.50 × 0.12 × 0.11 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with Atlas (Gemini ultra Cu) detector	2543 independent reflections
Radiation source: X-ray tube	2259 reflections with I > 3σ(I)
mirror	Rint = 0.024
Detector resolution: 10.3784 pixels mm-1	θmax = 66.6°, θmin = 4.9°
Rotation method data acquisition using ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009),	k = −11→11
Tmin = 0.714, Tmax = 1.000	l = −21→21
18522 measured reflections

Refinement on F2	76 constraints
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.098	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
S = 1.98	(Δ/σ)max = 0.013
2543 reflections	Δρmax = 0.17 e Å−3
190 parameters	Δρmin = −0.13 e Å−3
0 restraints

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.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
O1	0.84529 (8)	0.12294 (8)	0.81770 (4)	0.0248 (2)
O2	0.78640 (8)	0.15086 (8)	1.07814 (4)	0.0271 (2)
O3	0.16362 (8)	0.12599 (7)	0.48157 (4)	0.0244 (2)
N1	0.38690 (10)	0.18316 (9)	0.77253 (5)	0.0231 (3)
C1	0.59085 (11)	0.15330 (10)	0.86553 (6)	0.0206 (3)
C2	0.75506 (12)	0.13694 (10)	0.87911 (6)	0.0204 (3)
C3	0.81587 (11)	0.13725 (10)	0.95058 (6)	0.0220 (3)
C4	0.71412 (12)	0.15436 (10)	1.00995 (6)	0.0214 (3)
C5	0.55251 (12)	0.17397 (10)	0.99830 (6)	0.0229 (3)
C6	0.49391 (12)	0.17310 (10)	0.92638 (6)	0.0222 (3)
C7	0.52727 (11)	0.14440 (10)	0.79015 (6)	0.0207 (3)
C8	1.01066 (11)	0.09643 (12)	0.82857 (6)	0.0281 (3)
C9	0.68947 (13)	0.17194 (12)	1.14125 (6)	0.0284 (3)
C10	0.33285 (11)	0.16001 (11)	0.69888 (5)	0.0212 (3)
C11	0.23872 (11)	0.26224 (11)	0.66542 (6)	0.0243 (3)
C12	0.18457 (11)	0.24746 (11)	0.59337 (6)	0.0240 (3)
C13	0.22075 (11)	0.12870 (10)	0.55293 (5)	0.0210 (3)
C14	0.30901 (11)	0.02359 (11)	0.58635 (6)	0.0233 (3)
C15	0.36467 (11)	0.03995 (11)	0.65886 (6)	0.0229 (3)
C16	0.19378 (12)	0.00331 (11)	0.43883 (6)	0.0259 (3)
C17	0.13061 (13)	0.02869 (12)	0.36162 (6)	0.0309 (3)
H3	0.927413	0.125758	0.959322	0.0265*
H5	0.483291	0.187796	1.039282	0.0275*
H6	0.382532	0.186607	0.91805	0.0267*
H7	0.593525	0.107913	0.752123	0.0248*
H8a	1.059899	0.085896	0.781357	0.0337*
H8b	1.05849	0.172598	0.854758	0.0337*
H8c	1.024488	0.013012	0.856891	0.0337*
H9a	0.754648	0.173238	1.185267	0.0341*
H9b	0.634743	0.258688	1.136412	0.0341*
H9c	0.61388	0.098051	1.144473	0.0341*
H11	0.211463	0.343686	0.692928	0.0292*
H12	0.121631	0.319295	0.570909	0.0288*
H14	0.331465	−0.059847	0.559561	0.028*
H15	0.425927	−0.032629	0.681647	0.0274*
H16a	0.139336	−0.07389	0.4602	0.0311*
H16b	0.305721	−0.012837	0.437197	0.0311*
H17a	0.142647	−0.053732	0.332495	0.0371*
H17b	0.020596	0.052809	0.363673	0.0371*
H17c	0.188299	0.103188	0.339434	0.0371*

	U11	U22	U33	U12	U13	U23
O1	0.0173 (4)	0.0359 (4)	0.0213 (4)	0.0025 (3)	0.0015 (3)	−0.0005 (3)
O2	0.0258 (4)	0.0364 (5)	0.0190 (4)	0.0060 (3)	−0.0017 (3)	−0.0013 (3)
O3	0.0267 (4)	0.0261 (4)	0.0204 (4)	0.0031 (3)	−0.0028 (3)	−0.0019 (3)
N1	0.0203 (4)	0.0268 (5)	0.0222 (4)	0.0007 (3)	−0.0013 (3)	0.0002 (3)
C1	0.0193 (5)	0.0176 (5)	0.0248 (5)	−0.0007 (4)	−0.0006 (4)	0.0012 (4)
C2	0.0203 (5)	0.0180 (5)	0.0230 (5)	−0.0002 (4)	0.0021 (4)	0.0004 (4)
C3	0.0183 (5)	0.0225 (5)	0.0252 (6)	0.0013 (4)	−0.0018 (4)	−0.0005 (4)
C4	0.0249 (5)	0.0184 (5)	0.0208 (5)	0.0009 (4)	−0.0026 (4)	0.0001 (4)
C5	0.0233 (5)	0.0230 (5)	0.0226 (5)	0.0016 (4)	0.0038 (4)	0.0002 (4)
C6	0.0172 (5)	0.0224 (5)	0.0271 (5)	0.0009 (4)	−0.0003 (4)	0.0007 (4)
C7	0.0192 (5)	0.0200 (5)	0.0228 (5)	−0.0010 (4)	0.0025 (4)	0.0008 (4)
C8	0.0168 (5)	0.0392 (6)	0.0284 (5)	0.0011 (4)	0.0020 (4)	0.0011 (5)
C9	0.0338 (6)	0.0323 (6)	0.0193 (5)	0.0019 (5)	0.0022 (4)	−0.0003 (4)
C10	0.0155 (5)	0.0261 (5)	0.0222 (5)	−0.0015 (4)	0.0013 (4)	0.0005 (4)
C11	0.0212 (5)	0.0266 (6)	0.0252 (5)	0.0030 (4)	0.0009 (4)	−0.0028 (4)
C12	0.0207 (5)	0.0251 (6)	0.0262 (5)	0.0039 (4)	−0.0008 (4)	0.0010 (4)
C13	0.0174 (5)	0.0250 (5)	0.0206 (5)	−0.0023 (4)	0.0010 (4)	0.0012 (4)
C14	0.0222 (5)	0.0214 (5)	0.0264 (5)	−0.0006 (4)	−0.0002 (4)	−0.0022 (4)
C15	0.0194 (5)	0.0225 (5)	0.0266 (5)	0.0001 (4)	−0.0016 (4)	0.0031 (4)
C16	0.0257 (5)	0.0266 (6)	0.0256 (5)	0.0014 (4)	0.0001 (4)	−0.0040 (4)
C17	0.0347 (6)	0.0332 (6)	0.0248 (5)	0.0006 (5)	−0.0008 (4)	−0.0039 (4)

O1—C2	1.3626 (12)	C8—H8c	0.96
O1—C8	1.4317 (11)	C9—H9a	0.96
O2—C4	1.3662 (12)	C9—H9b	0.96
O2—C9	1.4286 (13)	C9—H9c	0.96
O3—C13	1.3690 (12)	C10—C11	1.3988 (14)
O3—C16	1.4385 (13)	C10—C15	1.3942 (14)
N1—C7	1.2795 (13)	C11—C12	1.3797 (14)
N1—C10	1.4171 (13)	C11—H11	0.96
C1—C2	1.4147 (14)	C12—C13	1.3957 (14)
C1—C6	1.3943 (14)	C12—H12	0.96
C1—C7	1.4578 (14)	C13—C14	1.3915 (14)
C2—C3	1.3814 (14)	C14—C15	1.3932 (14)
C3—C4	1.3948 (14)	C14—H14	0.96
C3—H3	0.96	C15—H15	0.96
C4—C5	1.3919 (14)	C16—C17	1.5051 (15)
C5—C6	1.3824 (14)	C16—H16a	0.96
C5—H5	0.96	C16—H16b	0.96
C6—H6	0.96	C17—H17a	0.96
C7—H7	0.96	C17—H17b	0.96
C8—H8a	0.96	C17—H17c	0.96
C8—H8b	0.96
C2—O1—C8	117.65 (7)	H9a—C9—H9b	109.4721
C4—O2—C9	117.48 (8)	H9a—C9—H9c	109.4713
C13—O3—C16	117.24 (8)	H9b—C9—H9c	109.4713
C7—N1—C10	118.11 (8)	N1—C10—C11	117.83 (9)
C2—C1—C6	117.78 (9)	N1—C10—C15	123.74 (9)
C2—C1—C7	120.11 (9)	C11—C10—C15	118.41 (9)
C6—C1—C7	122.08 (9)	C10—C11—C12	120.81 (10)
O1—C2—C1	115.49 (8)	C10—C11—H11	119.5938
O1—C2—C3	123.75 (9)	C12—C11—H11	119.5935
C1—C2—C3	120.75 (9)	C11—C12—C13	120.40 (9)
C2—C3—C4	119.55 (9)	C11—C12—H12	119.798
C2—C3—H3	120.2241	C13—C12—H12	119.7978
C4—C3—H3	120.2224	O3—C13—C12	115.53 (9)
O2—C4—C3	114.66 (9)	O3—C13—C14	124.96 (9)
O2—C4—C5	124.29 (9)	C12—C13—C14	119.50 (9)
C3—C4—C5	121.05 (9)	C13—C14—C15	119.71 (9)
C4—C5—C6	118.51 (9)	C13—C14—H14	120.1429
C4—C5—H5	120.7434	C15—C14—H14	120.1429
C6—C5—H5	120.7439	C10—C15—C14	121.08 (9)
C1—C6—C5	122.32 (9)	C10—C15—H15	119.46
C1—C6—H6	118.8378	C14—C15—H15	119.4596
C5—C6—H6	118.8386	O3—C16—C17	107.44 (8)
N1—C7—C1	122.80 (9)	O3—C16—H16a	109.4712
N1—C7—H7	118.601	O3—C16—H16b	109.4719
C1—C7—H7	118.601	C17—C16—H16a	109.471
O1—C8—H8a	109.4708	C17—C16—H16b	109.4701
O1—C8—H8b	109.4712	H16a—C16—H16b	111.434
O1—C8—H8c	109.4709	C16—C17—H17a	109.4709
H8a—C8—H8b	109.4718	C16—C17—H17b	109.4708
H8a—C8—H8c	109.4713	C16—C17—H17c	109.4707
H8b—C8—H8c	109.4713	H17a—C17—H17b	109.4715
O2—C9—H9a	109.4707	H17a—C17—H17c	109.4719
O2—C9—H9b	109.4712	H17b—C17—H17c	109.4715
O2—C9—H9c	109.4708
C8—O1—C2—C1	−175.74 (9)	O1—C2—C3—C4	179.02 (9)
C8—O1—C2—C3	4.99 (14)	C1—C2—C3—C4	−0.22 (15)
C9—O2—C4—C3	178.16 (9)	C2—C3—C4—O2	179.02 (9)
C9—O2—C4—C5	−1.49 (14)	C2—C3—C4—C5	−1.32 (15)
C16—O3—C13—C12	−177.94 (8)	O2—C4—C5—C6	−178.96 (9)
C16—O3—C13—C14	1.80 (13)	C3—C4—C5—C6	1.42 (14)
C13—O3—C16—C17	−176.02 (8)	C4—C5—C6—C1	0.03 (16)
C10—N1—C7—C1	−175.18 (9)	N1—C10—C11—C12	178.79 (9)
C7—N1—C10—C11	−141.76 (10)	C15—C10—C11—C12	−2.88 (14)
C7—N1—C10—C15	40.01 (14)	N1—C10—C15—C14	−179.59 (9)
C6—C1—C2—O1	−177.72 (9)	C11—C10—C15—C14	2.20 (14)
C6—C1—C2—C3	1.57 (14)	C10—C11—C12—C13	1.09 (15)
C7—C1—C2—O1	4.41 (13)	C11—C12—C13—O3	−178.79 (9)
C7—C1—C2—C3	−176.30 (9)	C11—C12—C13—C14	1.45 (14)
C2—C1—C6—C5	−1.49 (15)	O3—C13—C14—C15	178.14 (9)
C7—C1—C6—C5	176.34 (9)	C12—C13—C14—C15	−2.12 (14)
C2—C1—C7—N1	−166.67 (10)	C13—C14—C15—C10	0.29 (15)
C6—C1—C7—N1	15.55 (15)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8c···O2i	0.96	2.52	3.3745 (13)	148
C5—H5···Cg2ii	0.96	2.88	3.7529 (11)	152
C14—H14···Cg1iii	0.96	2.76	3.6019 (11)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8c⋯O2i	0.96	2.52	3.3745 (13)	148
C5—H5⋯Cg2ii	0.96	2.88	3.7529 (11)	152
C14—H14⋯Cg1iii	0.96	2.76	3.6019 (11)	147

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