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

Yang, S.-P.; Han, L.-J.; Wang, D.-Q.; Xia, H.-T.

doi:10.1107/S1600536806037366

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

S.-P. Yang, L.-J. Han, D.-Q. Wang and H.-T. Xia

In the title compound, C₁₈H₁₇N₃O₄, the molecule has a trans configuration; the dihedral angle between the benzene rings is 34.4 (1)°. The molecules are linked into centrosymmetric dimers with edge-fused [R₂¹(6)][R₂²(10)][R₂¹(6)] rings by C—H

O hydrogen bonds, and these dimers are linked by C—H

O weak interactions into a ribbon along [101]. Adjacent ribbons are linked into a three-dimensional network structure by π–π stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037366/ez2031sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037366/ez2031Isup2.hkl Contains datablock I

CCDC reference: 616610

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
R factor = 0.061
wR factor = 0.237
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         39 Perc.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit     -P21/c
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18B   ..  O4      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O2      ..       2.67 Ang.

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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-nitrophenyl)propenoyl]oxime top

Crystal data top

C₁₈H₁₇N₃O₄	F(000) = 712
M_r = 339.35	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 453 K
Hall symbol: -P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.031 (12) Å	Cell parameters from 875 reflections
b = 7.332 (5) Å	θ = 2.3–20.4°
c = 12.714 (9) Å	µ = 0.10 mm⁻¹
β = 99.338 (11)°	T = 298 K
V = 1659 (2) Å³	Needle, red
Z = 4	0.46 × 0.43 × 0.25 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2921 independent reflections
Radiation source: fine-focus sealed tube	1142 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
T_min = 0.956, T_max = 0.976	k = −8→8
8286 measured reflections	l = −15→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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.237	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + 0.7102P] where P = (F_o² + 2F_c²)/3
2921 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

Experimental. IR (KBr disk): 1748, 1638, 1600 cm^-1.

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
N1	0.8959 (2)	0.2646 (6)	1.0208 (4)	0.0634 (13)
N2	0.4335 (2)	0.3501 (6)	0.6726 (4)	0.0650 (13)
N3	0.1317 (2)	0.3825 (6)	0.3351 (4)	0.0667 (13)
O1	0.51241 (16)	0.3451 (5)	0.7166 (3)	0.0593 (10)
O2	0.47342 (19)	0.3797 (6)	0.8728 (3)	0.0859 (14)
O3	0.88809 (19)	0.1982 (6)	0.9322 (3)	0.0855 (14)
O4	0.9568 (2)	0.2841 (6)	1.0761 (4)	0.0999 (16)
C1	0.5233 (3)	0.3587 (7)	0.8238 (4)	0.0514 (13)
C2	0.6026 (2)	0.3480 (6)	0.8705 (4)	0.0517 (13)
H2	0.6384	0.3197	0.8280	0.062*
C3	0.6232 (2)	0.3785 (6)	0.9724 (4)	0.0509 (13)
H3	0.5841	0.4064	1.0093	0.061*
C4	0.6974 (2)	0.3756 (6)	1.0371 (4)	0.0448 (12)
C5	0.7604 (2)	0.3198 (6)	0.9979 (4)	0.0457 (12)
H5	0.7568	0.2803	0.9278	0.055*
C6	0.8292 (2)	0.3230 (6)	1.0640 (4)	0.0475 (13)
C7	0.8373 (3)	0.3757 (7)	1.1684 (4)	0.0574 (14)
H7	0.8842	0.3750	1.2114	0.069*
C8	0.7741 (3)	0.4299 (7)	1.2084 (4)	0.0580 (14)
H8	0.7779	0.4656	1.2793	0.070*
C9	0.7051 (3)	0.4310 (6)	1.1428 (4)	0.0522 (13)
H9	0.6628	0.4696	1.1700	0.063*
C10	0.4249 (3)	0.3583 (6)	0.5736 (4)	0.0487 (13)
H10	0.4665	0.3624	0.5391	0.058*
C11	0.3496 (2)	0.3612 (6)	0.5119 (4)	0.0451 (12)
C12	0.2869 (3)	0.3234 (6)	0.5574 (4)	0.0509 (13)
H12	0.2934	0.2931	0.6294	0.061*
C13	0.2155 (3)	0.3286 (7)	0.5012 (4)	0.0535 (14)
H13	0.1748	0.3017	0.5348	0.064*
C14	0.2038 (2)	0.3746 (6)	0.3924 (4)	0.0485 (13)
C15	0.2664 (3)	0.4122 (6)	0.3462 (4)	0.0520 (13)
H15	0.2603	0.4439	0.2745	0.062*
C16	0.3372 (2)	0.4034 (6)	0.4043 (4)	0.0487 (13)
H16	0.3782	0.4266	0.3704	0.058*
C17	0.0674 (3)	0.3227 (8)	0.3814 (5)	0.0817 (19)
H17A	0.0685	0.1923	0.3884	0.123*
H17B	0.0219	0.3588	0.3360	0.123*
H17C	0.0692	0.3773	0.4504	0.123*
C18	0.1184 (3)	0.4159 (9)	0.2234 (5)	0.092 (2)
H18A	0.1514	0.5105	0.2068	0.137*
H18B	0.0671	0.4535	0.2018	0.137*
H18C	0.1275	0.3064	0.1861	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.040 (3)	0.081 (4)	0.066 (3)	0.000 (2)	0.002 (2)	0.000 (3)
N2	0.036 (2)	0.103 (4)	0.052 (3)	−0.002 (2)	−0.008 (2)	−0.002 (3)
N3	0.038 (2)	0.094 (4)	0.064 (3)	−0.001 (2)	−0.004 (2)	0.005 (3)
O1	0.0358 (18)	0.094 (3)	0.045 (2)	0.0018 (17)	−0.0023 (15)	−0.001 (2)
O2	0.041 (2)	0.159 (4)	0.056 (3)	−0.003 (2)	0.0017 (19)	−0.010 (2)
O3	0.058 (2)	0.135 (4)	0.062 (3)	0.012 (2)	0.007 (2)	−0.010 (3)
O4	0.038 (2)	0.153 (4)	0.103 (4)	0.004 (2)	−0.008 (2)	−0.033 (3)
C1	0.040 (3)	0.066 (4)	0.046 (3)	−0.006 (3)	−0.001 (3)	0.001 (3)
C2	0.036 (3)	0.065 (4)	0.052 (3)	0.002 (2)	0.001 (2)	−0.001 (3)
C3	0.039 (3)	0.055 (3)	0.057 (4)	0.004 (2)	0.004 (3)	−0.001 (3)
C4	0.039 (3)	0.050 (3)	0.043 (3)	0.003 (2)	−0.002 (2)	0.003 (2)
C5	0.041 (3)	0.048 (3)	0.045 (3)	−0.003 (2)	−0.002 (2)	−0.001 (2)
C6	0.040 (3)	0.052 (3)	0.050 (3)	0.004 (2)	0.003 (2)	0.001 (3)
C7	0.053 (3)	0.061 (4)	0.050 (4)	0.004 (3)	−0.017 (3)	−0.002 (3)
C8	0.062 (4)	0.061 (4)	0.047 (3)	0.005 (3)	−0.003 (3)	−0.006 (3)
C9	0.048 (3)	0.056 (3)	0.051 (3)	0.006 (3)	0.004 (2)	0.002 (3)
C10	0.044 (3)	0.060 (3)	0.042 (3)	−0.001 (2)	0.004 (2)	−0.001 (3)
C11	0.041 (3)	0.048 (3)	0.044 (3)	−0.004 (2)	0.001 (2)	−0.004 (2)
C12	0.051 (3)	0.059 (3)	0.041 (3)	−0.003 (3)	0.004 (2)	0.002 (2)
C13	0.044 (3)	0.068 (4)	0.050 (3)	−0.001 (3)	0.010 (2)	0.006 (3)
C14	0.036 (3)	0.049 (3)	0.059 (4)	0.001 (2)	0.002 (2)	−0.006 (3)
C15	0.048 (3)	0.063 (4)	0.043 (3)	−0.001 (3)	0.003 (2)	−0.005 (3)
C16	0.041 (3)	0.062 (4)	0.044 (3)	−0.003 (2)	0.009 (2)	−0.005 (3)
C17	0.039 (3)	0.100 (5)	0.105 (5)	−0.009 (3)	0.010 (3)	−0.015 (4)
C18	0.057 (4)	0.135 (6)	0.072 (5)	0.003 (4)	−0.018 (3)	−0.007 (4)

Geometric parameters (Å, º) top

N1—O4	1.212 (5)	C8—C9	1.381 (6)
N1—O3	1.215 (5)	C8—H8	0.9300
N1—C6	1.465 (6)	C9—H9	0.9300
N2—C10	1.245 (6)	C10—C11	1.454 (6)
N2—O1	1.442 (5)	C10—H10	0.9300
N3—C14	1.384 (6)	C11—C12	1.380 (6)
N3—C18	1.423 (6)	C11—C16	1.385 (6)
N3—C17	1.451 (6)	C12—C13	1.367 (6)
O1—C1	1.349 (6)	C12—H12	0.9300
O2—C1	1.185 (5)	C13—C14	1.406 (6)
C1—C2	1.458 (6)	C13—H13	0.9300
C2—C3	1.308 (6)	C14—C15	1.381 (6)
C2—H2	0.9300	C15—C16	1.369 (6)
C3—C4	1.453 (6)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.376 (6)	C17—H17A	0.9600
C4—C9	1.389 (6)	C17—H17B	0.9600
C5—C6	1.381 (6)	C17—H17C	0.9600
C5—H5	0.9300	C18—H18A	0.9600
C6—C7	1.367 (6)	C18—H18B	0.9600
C7—C8	1.380 (6)	C18—H18C	0.9600
C7—H7	0.9300

O4—N1—O3	122.9 (5)	C4—C9—H9	119.3
O4—N1—C6	118.0 (5)	N2—C10—C11	120.0 (5)
O3—N1—C6	119.1 (4)	N2—C10—H10	120.0
C10—N2—O1	110.3 (4)	C11—C10—H10	120.0
C14—N3—C18	121.7 (4)	C12—C11—C16	116.6 (4)
C14—N3—C17	121.2 (5)	C12—C11—C10	121.8 (5)
C18—N3—C17	116.1 (4)	C16—C11—C10	121.5 (4)
C1—O1—N2	111.3 (3)	C13—C12—C11	122.7 (5)
O2—C1—O1	122.8 (4)	C13—C12—H12	118.7
O2—C1—C2	124.8 (5)	C11—C12—H12	118.7
O1—C1—C2	112.4 (5)	C12—C13—C14	120.0 (4)
C3—C2—C1	119.7 (5)	C12—C13—H13	120.0
C3—C2—H2	120.1	C14—C13—H13	120.0
C1—C2—H2	120.1	C15—C14—N3	122.0 (5)
C2—C3—C4	130.2 (5)	C15—C14—C13	117.6 (4)
C2—C3—H3	114.9	N3—C14—C13	120.4 (5)
C4—C3—H3	114.9	C16—C15—C14	121.1 (5)
C5—C4—C9	118.6 (4)	C16—C15—H15	119.5
C5—C4—C3	122.6 (5)	C14—C15—H15	119.5
C9—C4—C3	118.8 (4)	C15—C16—C11	122.0 (4)
C4—C5—C6	119.3 (5)	C15—C16—H16	119.0
C4—C5—H5	120.4	C11—C16—H16	119.0
C6—C5—H5	120.4	N3—C17—H17A	109.5
C7—C6—C5	122.6 (5)	N3—C17—H17B	109.5
C7—C6—N1	118.8 (5)	H17A—C17—H17B	109.5
C5—C6—N1	118.6 (5)	N3—C17—H17C	109.5
C6—C7—C8	118.4 (5)	H17A—C17—H17C	109.5
C6—C7—H7	120.8	H17B—C17—H17C	109.5
C8—C7—H7	120.8	N3—C18—H18A	109.5
C7—C8—C9	119.8 (5)	N3—C18—H18B	109.5
C7—C8—H8	120.1	H18A—C18—H18B	109.5
C9—C8—H8	120.1	N3—C18—H18C	109.5
C8—C9—C4	121.4 (5)	H18A—C18—H18C	109.5
C8—C9—H9	119.3	H18B—C18—H18C	109.5

C10—N2—O1—C1	172.5 (4)	C5—C4—C9—C8	−0.3 (7)
N2—O1—C1—O2	−2.9 (7)	C3—C4—C9—C8	179.5 (4)
N2—O1—C1—C2	178.2 (4)	O1—N2—C10—C11	178.9 (4)
O2—C1—C2—C3	−6.2 (8)	N2—C10—C11—C12	−11.6 (7)
O1—C1—C2—C3	172.7 (4)	N2—C10—C11—C16	168.0 (5)
C1—C2—C3—C4	179.7 (5)	C16—C11—C12—C13	−0.8 (7)
C2—C3—C4—C5	−6.5 (8)	C10—C11—C12—C13	178.8 (4)
C2—C3—C4—C9	173.7 (5)	C11—C12—C13—C14	−0.2 (8)
C9—C4—C5—C6	−0.9 (7)	C18—N3—C14—C15	5.0 (8)
C3—C4—C5—C6	179.2 (4)	C17—N3—C14—C15	172.9 (5)
C4—C5—C6—C7	1.6 (7)	C18—N3—C14—C13	−175.5 (5)
C4—C5—C6—N1	−179.5 (4)	C17—N3—C14—C13	−7.6 (7)
O4—N1—C6—C7	−7.9 (7)	C12—C13—C14—C15	0.4 (7)
O3—N1—C6—C7	171.7 (5)	C12—C13—C14—N3	−179.2 (4)
O4—N1—C6—C5	173.1 (5)	N3—C14—C15—C16	−180.0 (5)
O3—N1—C6—C5	−7.3 (7)	C13—C14—C15—C16	0.5 (7)
C5—C6—C7—C8	−0.8 (7)	C14—C15—C16—C11	−1.6 (7)
N1—C6—C7—C8	−179.8 (4)	C12—C11—C16—C15	1.7 (7)
C6—C7—C8—C9	−0.5 (7)	C10—C11—C16—C15	−177.9 (4)
C7—C8—C9—C4	1.1 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O4ⁱ	0.96	2.65	3.340 (7)	129
C3—H3···O2ⁱⁱ	0.93	2.51	3.341 (7)	149
C9—H9···O2ⁱⁱ	0.93	2.67	3.481 (6)	146

Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, −y+1, −z+2.

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

Supporting information

Key indicators

checkCIF/PLATON results

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