(E,E)-4-(Dimethyl­amino)­benzaldehyde O-[3-(3-chloro­phen­yl)propeno­yl]oxime

Yang, S.-P.; Han, L.-J.; Wang, D.-Q.; Ding, T.-Z.

doi:10.1107/S1600536806043741

(E,E)-4-(Dimethylamino)benzaldehyde O-[3-(3-chlorophenyl)propenoyl]oxime

S.-P. Yang, L.-J. Han, D.-Q. Wang and T.-Z. Ding

In the title compound, C₁₈H₁₇ClN₂O₂, the molecule has a trans configuration (E,E), and the dihedral angle between the benzene rings is 4.3 (2)°. One C—H

O and one C—H

N hydrogen bond form an R₁²(5) motif.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043741/at2137sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043741/at2137Isup2.hkl Contains datablock I

CCDC reference: 607189

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.050
wR factor = 0.131
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  O2      ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  N1      ..       2.83 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E,E)-4-(Dimethylamino)benzaldehyde O-[3-(3-chlorophenyl)propenoyl]oxime top

Crystal data top

C₁₈H₁₇ClN₂O₂	Z = 2
M_r = 328.79	F(000) = 344
Triclinic, P1	D_x = 1.346 Mg m⁻³
Hall symbol: -P 1	Melting point: 436 K
a = 8.161 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.792 (3) Å	Cell parameters from 1077 reflections
c = 11.228 (4) Å	θ = 2.4–22.6°
α = 108.706 (5)°	µ = 0.25 mm⁻¹
β = 104.242 (5)°	T = 298 K
γ = 94.628 (5)°	Columnar, yellow
V = 811.1 (5) Å³	0.45 × 0.28 × 0.15 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2840 independent reflections
Radiation source: fine-focus sealed tube	1623 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.897, T_max = 0.964	k = −11→9
4304 measured reflections	l = −8→13

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0554P)² + 0.0567P] where P = (F_o² + 2F_c²)/3
2840 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.47606 (11)	−0.31483 (8)	−0.53841 (8)	0.0756 (3)
N1	0.2248 (3)	0.6025 (2)	0.0179 (2)	0.0597 (7)
N2	0.0979 (3)	1.2383 (2)	0.3388 (2)	0.0622 (7)
O1	0.2443 (3)	0.45227 (18)	−0.00377 (18)	0.0638 (6)
O2	0.3118 (4)	0.4463 (2)	−0.1870 (2)	0.1073 (10)
C1	0.2900 (4)	0.3877 (3)	−0.1135 (3)	0.0597 (8)
C2	0.3081 (4)	0.2377 (3)	−0.1265 (3)	0.0568 (8)
H2	0.2849	0.2020	−0.0638	0.068*
C3	0.3556 (4)	0.1507 (3)	−0.2226 (3)	0.0544 (8)
H3	0.3803	0.1919	−0.2816	0.065*
C4	0.3750 (3)	−0.0024 (3)	−0.2499 (3)	0.0466 (7)
C5	0.4150 (3)	−0.0782 (3)	−0.3637 (2)	0.0512 (7)
H5	0.4311	−0.0305	−0.4206	0.061*
C6	0.4310 (3)	−0.2230 (3)	−0.3930 (3)	0.0499 (7)
C7	0.4089 (4)	−0.2952 (3)	−0.3105 (3)	0.0601 (8)
H7	0.4188	−0.3935	−0.3315	0.072*
C8	0.3718 (4)	−0.2211 (3)	−0.1962 (3)	0.0633 (8)
H8	0.3589	−0.2689	−0.1388	0.076*
C9	0.3537 (4)	−0.0766 (3)	−0.1666 (3)	0.0580 (8)
H9	0.3270	−0.0279	−0.0898	0.070*
C10	0.1916 (4)	0.6533 (3)	0.1263 (3)	0.0555 (8)
H10	0.1837	0.5927	0.1744	0.067*
C11	0.1652 (3)	0.8034 (3)	0.1780 (2)	0.0478 (7)
C12	0.1688 (4)	0.8991 (3)	0.1108 (3)	0.0545 (8)
H12	0.1867	0.8667	0.0284	0.065*
C13	0.1465 (4)	1.0404 (3)	0.1632 (3)	0.0559 (8)
H13	0.1497	1.1018	0.1152	0.067*
C14	0.1190 (3)	1.0959 (3)	0.2866 (3)	0.0486 (7)
C15	0.1155 (4)	0.9988 (3)	0.3538 (3)	0.0575 (8)
H15	0.0981	1.0306	0.4364	0.069*
C16	0.1375 (4)	0.8571 (3)	0.2998 (3)	0.0572 (8)
H16	0.1337	0.7949	0.3469	0.069*
C17	0.1051 (5)	1.3400 (3)	0.2704 (3)	0.0812 (10)
H17A	0.1063	1.4369	0.3280	0.122*
H17B	0.0064	1.3123	0.1949	0.122*
H17C	0.2075	1.3384	0.2427	0.122*
C18	0.0621 (4)	1.2906 (3)	0.4644 (3)	0.0805 (10)
H18A	0.0456	1.3905	0.4841	0.121*
H18B	0.1570	1.2845	0.5317	0.121*
H18C	−0.0400	1.2313	0.4608	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0972 (7)	0.0614 (5)	0.0691 (5)	0.0286 (4)	0.0378 (5)	0.0105 (4)
N1	0.0840 (19)	0.0368 (13)	0.0641 (16)	0.0184 (12)	0.0312 (14)	0.0161 (11)
N2	0.0802 (19)	0.0448 (14)	0.0638 (15)	0.0212 (13)	0.0302 (14)	0.0125 (12)
O1	0.0966 (17)	0.0388 (11)	0.0696 (13)	0.0245 (10)	0.0439 (12)	0.0191 (9)
O2	0.217 (3)	0.0509 (13)	0.0936 (17)	0.0471 (16)	0.0925 (19)	0.0368 (13)
C1	0.080 (2)	0.0408 (16)	0.0605 (19)	0.0129 (15)	0.0280 (17)	0.0142 (14)
C2	0.077 (2)	0.0414 (15)	0.0604 (18)	0.0129 (14)	0.0293 (16)	0.0211 (14)
C3	0.076 (2)	0.0400 (15)	0.0557 (17)	0.0125 (14)	0.0300 (16)	0.0194 (13)
C4	0.0508 (18)	0.0399 (15)	0.0536 (16)	0.0108 (13)	0.0220 (14)	0.0164 (12)
C5	0.058 (2)	0.0456 (16)	0.0550 (17)	0.0103 (14)	0.0223 (15)	0.0194 (13)
C6	0.0514 (19)	0.0406 (15)	0.0562 (17)	0.0121 (13)	0.0185 (14)	0.0119 (13)
C7	0.069 (2)	0.0407 (16)	0.076 (2)	0.0169 (15)	0.0268 (17)	0.0214 (15)
C8	0.085 (2)	0.0477 (17)	0.075 (2)	0.0189 (16)	0.0379 (18)	0.0323 (15)
C9	0.078 (2)	0.0499 (17)	0.0596 (18)	0.0176 (15)	0.0370 (17)	0.0227 (14)
C10	0.069 (2)	0.0455 (16)	0.0564 (18)	0.0113 (14)	0.0245 (16)	0.0189 (14)
C11	0.0564 (19)	0.0414 (15)	0.0464 (15)	0.0074 (13)	0.0191 (14)	0.0135 (12)
C12	0.072 (2)	0.0511 (17)	0.0434 (15)	0.0126 (15)	0.0260 (15)	0.0129 (13)
C13	0.079 (2)	0.0436 (16)	0.0512 (17)	0.0141 (15)	0.0235 (16)	0.0198 (13)
C14	0.0469 (18)	0.0436 (16)	0.0519 (16)	0.0080 (13)	0.0147 (14)	0.0119 (13)
C15	0.078 (2)	0.0517 (17)	0.0504 (16)	0.0149 (15)	0.0341 (16)	0.0154 (14)
C16	0.076 (2)	0.0487 (16)	0.0562 (17)	0.0143 (15)	0.0298 (16)	0.0222 (14)
C17	0.104 (3)	0.0480 (18)	0.094 (2)	0.0186 (18)	0.030 (2)	0.0260 (18)
C18	0.090 (3)	0.068 (2)	0.083 (2)	0.0301 (19)	0.043 (2)	0.0096 (17)

Geometric parameters (Å, º) top

Cl1—C6	1.737 (3)	C8—H8	0.9300
N1—C10	1.263 (3)	C9—H9	0.9300
N1—O1	1.441 (3)	C10—C11	1.453 (3)
N2—C14	1.371 (3)	C10—H10	0.9300
N2—C17	1.446 (3)	C11—C12	1.381 (3)
N2—C18	1.450 (3)	C11—C16	1.381 (3)
O1—C1	1.350 (3)	C12—C13	1.366 (3)
O2—C1	1.184 (3)	C12—H12	0.9300
C1—C2	1.452 (4)	C13—C14	1.398 (3)
C2—C3	1.308 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.393 (4)
C3—C4	1.461 (3)	C15—C16	1.371 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.388 (3)	C16—H16	0.9300
C4—C9	1.388 (4)	C17—H17A	0.9600
C5—C6	1.374 (3)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.368 (4)	C18—H18A	0.9600
C7—C8	1.376 (4)	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600
C8—C9	1.375 (3)

C10—N1—O1	107.9 (2)	N1—C10—H10	119.0
C14—N2—C17	122.0 (2)	C11—C10—H10	119.0
C14—N2—C18	120.4 (2)	C12—C11—C16	117.0 (2)
C17—N2—C18	117.6 (2)	C12—C11—C10	122.7 (2)
C1—O1—N1	113.7 (2)	C16—C11—C10	120.3 (3)
O2—C1—O1	124.3 (3)	C13—C12—C11	121.2 (3)
O2—C1—C2	125.9 (3)	C13—C12—H12	119.4
O1—C1—C2	109.8 (3)	C11—C12—H12	119.4
C3—C2—C1	122.7 (3)	C12—C13—C14	122.2 (3)
C3—C2—H2	118.7	C12—C13—H13	118.9
C1—C2—H2	118.7	C14—C13—H13	118.9
C2—C3—C4	128.7 (3)	N2—C14—C15	121.9 (2)
C2—C3—H3	115.7	N2—C14—C13	121.8 (3)
C4—C3—H3	115.7	C15—C14—C13	116.2 (2)
C5—C4—C9	118.2 (2)	C16—C15—C14	120.9 (3)
C5—C4—C3	119.2 (2)	C16—C15—H15	119.5
C9—C4—C3	122.6 (2)	C14—C15—H15	119.5
C6—C5—C4	120.5 (3)	C15—C16—C11	122.4 (3)
C6—C5—H5	119.8	C15—C16—H16	118.8
C4—C5—H5	119.8	C11—C16—H16	118.8
C7—C6—C5	120.8 (3)	N2—C17—H17A	109.5
C7—C6—Cl1	120.2 (2)	N2—C17—H17B	109.5
C5—C6—Cl1	119.0 (2)	H17A—C17—H17B	109.5
C6—C7—C8	119.4 (2)	N2—C17—H17C	109.5
C6—C7—H7	120.3	H17A—C17—H17C	109.5
C8—C7—H7	120.3	H17B—C17—H17C	109.5
C9—C8—C7	120.2 (3)	N2—C18—H18A	109.5
C9—C8—H8	119.9	N2—C18—H18B	109.5
C7—C8—H8	119.9	H18A—C18—H18B	109.5
C8—C9—C4	120.9 (3)	N2—C18—H18C	109.5
C8—C9—H9	119.6	H18A—C18—H18C	109.5
C4—C9—H9	119.6	H18B—C18—H18C	109.5
N1—C10—C11	122.0 (3)

C10—N1—O1—C1	−176.4 (2)	O1—N1—C10—C11	179.6 (2)
N1—O1—C1—O2	−0.4 (4)	N1—C10—C11—C12	2.3 (4)
N1—O1—C1—C2	179.5 (2)	N1—C10—C11—C16	−176.8 (3)
O2—C1—C2—C3	1.6 (5)	C16—C11—C12—C13	0.2 (4)
O1—C1—C2—C3	−178.3 (3)	C10—C11—C12—C13	−178.8 (3)
C1—C2—C3—C4	−178.4 (3)	C11—C12—C13—C14	0.0 (5)
C2—C3—C4—C5	175.2 (3)	C17—N2—C14—C15	178.6 (3)
C2—C3—C4—C9	−4.2 (5)	C18—N2—C14—C15	−3.2 (4)
C9—C4—C5—C6	0.7 (4)	C17—N2—C14—C13	−0.9 (4)
C3—C4—C5—C6	−178.8 (2)	C18—N2—C14—C13	177.3 (3)
C4—C5—C6—C7	−0.4 (4)	C12—C13—C14—N2	179.6 (3)
C4—C5—C6—Cl1	178.5 (2)	C12—C13—C14—C15	0.0 (4)
C5—C6—C7—C8	−0.6 (4)	N2—C14—C15—C16	−179.8 (3)
Cl1—C6—C7—C8	−179.5 (2)	C13—C14—C15—C16	−0.2 (4)
C6—C7—C8—C9	1.3 (5)	C14—C15—C16—C11	0.5 (5)
C7—C8—C9—C4	−1.0 (5)	C12—C11—C16—C15	−0.5 (4)
C5—C4—C9—C8	0.0 (4)	C10—C11—C16—C15	178.6 (3)
C3—C4—C9—C8	179.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2ⁱ	0.93	2.64	3.292 (3)	128
C8—H8···N1ⁱ	0.93	2.83	3.735 (4)	164

Symmetry code: (i) x, y−1, z.

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(E,E)-4-(Dimethyl­amino)­benzaldehyde O-[3-(3-chloro­phen­yl)propeno­yl]oxime

Supporting information

Key indicators

checkCIF/PLATON results

(E,E)-4-(Dimethylamino)benzaldehyde O-[3-(3-chlorophenyl)propenoyl]oxime