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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043741/at2137sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043741/at2137Isup2.hkl
Contains datablock I

CCDC reference: 607189

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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
C18H17ClN2O2Z = 2
Mr = 328.79F(000) = 344
Triclinic, P1Dx = 1.346 Mg m3
Hall symbol: -P 1Melting point: 436 K
a = 8.161 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.792 (3) ÅCell parameters from 1077 reflections
c = 11.228 (4) Åθ = 2.4–22.6°
α = 108.706 (5)°µ = 0.25 mm1
β = 104.242 (5)°T = 298 K
γ = 94.628 (5)°Columnar, yellow
V = 811.1 (5) Å30.45 × 0.28 × 0.15 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2840 independent reflections
Radiation source: fine-focus sealed tube1623 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.897, Tmax = 0.964k = 119
4304 measured reflectionsl = 813
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0554P)2 + 0.0567P]
where P = (Fo2 + 2Fc2)/3
2840 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
Cl10.47606 (11)0.31483 (8)0.53841 (8)0.0756 (3)
N10.2248 (3)0.6025 (2)0.0179 (2)0.0597 (7)
N20.0979 (3)1.2383 (2)0.3388 (2)0.0622 (7)
O10.2443 (3)0.45227 (18)0.00377 (18)0.0638 (6)
O20.3118 (4)0.4463 (2)0.1870 (2)0.1073 (10)
C10.2900 (4)0.3877 (3)0.1135 (3)0.0597 (8)
C20.3081 (4)0.2377 (3)0.1265 (3)0.0568 (8)
H20.28490.20200.06380.068*
C30.3556 (4)0.1507 (3)0.2226 (3)0.0544 (8)
H30.38030.19190.28160.065*
C40.3750 (3)0.0024 (3)0.2499 (3)0.0466 (7)
C50.4150 (3)0.0782 (3)0.3637 (2)0.0512 (7)
H50.43110.03050.42060.061*
C60.4310 (3)0.2230 (3)0.3930 (3)0.0499 (7)
C70.4089 (4)0.2952 (3)0.3105 (3)0.0601 (8)
H70.41880.39350.33150.072*
C80.3718 (4)0.2211 (3)0.1962 (3)0.0633 (8)
H80.35890.26890.13880.076*
C90.3537 (4)0.0766 (3)0.1666 (3)0.0580 (8)
H90.32700.02790.08980.070*
C100.1916 (4)0.6533 (3)0.1263 (3)0.0555 (8)
H100.18370.59270.17440.067*
C110.1652 (3)0.8034 (3)0.1780 (2)0.0478 (7)
C120.1688 (4)0.8991 (3)0.1108 (3)0.0545 (8)
H120.18670.86670.02840.065*
C130.1465 (4)1.0404 (3)0.1632 (3)0.0559 (8)
H130.14971.10180.11520.067*
C140.1190 (3)1.0959 (3)0.2866 (3)0.0486 (7)
C150.1155 (4)0.9988 (3)0.3538 (3)0.0575 (8)
H150.09811.03060.43640.069*
C160.1375 (4)0.8571 (3)0.2998 (3)0.0572 (8)
H160.13370.79490.34690.069*
C170.1051 (5)1.3400 (3)0.2704 (3)0.0812 (10)
H17A0.10631.43690.32800.122*
H17B0.00641.31230.19490.122*
H17C0.20751.33840.24270.122*
C180.0621 (4)1.2906 (3)0.4644 (3)0.0805 (10)
H18A0.04561.39050.48410.121*
H18B0.15701.28450.53170.121*
H18C0.04001.23130.46080.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0972 (7)0.0614 (5)0.0691 (5)0.0286 (4)0.0378 (5)0.0105 (4)
N10.0840 (19)0.0368 (13)0.0641 (16)0.0184 (12)0.0312 (14)0.0161 (11)
N20.0802 (19)0.0448 (14)0.0638 (15)0.0212 (13)0.0302 (14)0.0125 (12)
O10.0966 (17)0.0388 (11)0.0696 (13)0.0245 (10)0.0439 (12)0.0191 (9)
O20.217 (3)0.0509 (13)0.0936 (17)0.0471 (16)0.0925 (19)0.0368 (13)
C10.080 (2)0.0408 (16)0.0605 (19)0.0129 (15)0.0280 (17)0.0142 (14)
C20.077 (2)0.0414 (15)0.0604 (18)0.0129 (14)0.0293 (16)0.0211 (14)
C30.076 (2)0.0400 (15)0.0557 (17)0.0125 (14)0.0300 (16)0.0194 (13)
C40.0508 (18)0.0399 (15)0.0536 (16)0.0108 (13)0.0220 (14)0.0164 (12)
C50.058 (2)0.0456 (16)0.0550 (17)0.0103 (14)0.0223 (15)0.0194 (13)
C60.0514 (19)0.0406 (15)0.0562 (17)0.0121 (13)0.0185 (14)0.0119 (13)
C70.069 (2)0.0407 (16)0.076 (2)0.0169 (15)0.0268 (17)0.0214 (15)
C80.085 (2)0.0477 (17)0.075 (2)0.0189 (16)0.0379 (18)0.0323 (15)
C90.078 (2)0.0499 (17)0.0596 (18)0.0176 (15)0.0370 (17)0.0227 (14)
C100.069 (2)0.0455 (16)0.0564 (18)0.0113 (14)0.0245 (16)0.0189 (14)
C110.0564 (19)0.0414 (15)0.0464 (15)0.0074 (13)0.0191 (14)0.0135 (12)
C120.072 (2)0.0511 (17)0.0434 (15)0.0126 (15)0.0260 (15)0.0129 (13)
C130.079 (2)0.0436 (16)0.0512 (17)0.0141 (15)0.0235 (16)0.0198 (13)
C140.0469 (18)0.0436 (16)0.0519 (16)0.0080 (13)0.0147 (14)0.0119 (13)
C150.078 (2)0.0517 (17)0.0504 (16)0.0149 (15)0.0341 (16)0.0154 (14)
C160.076 (2)0.0487 (16)0.0562 (17)0.0143 (15)0.0298 (16)0.0222 (14)
C170.104 (3)0.0480 (18)0.094 (2)0.0186 (18)0.030 (2)0.0260 (18)
C180.090 (3)0.068 (2)0.083 (2)0.0301 (19)0.043 (2)0.0096 (17)
Geometric parameters (Å, º) top
Cl1—C61.737 (3)C8—H80.9300
N1—C101.263 (3)C9—H90.9300
N1—O11.441 (3)C10—C111.453 (3)
N2—C141.371 (3)C10—H100.9300
N2—C171.446 (3)C11—C121.381 (3)
N2—C181.450 (3)C11—C161.381 (3)
O1—C11.350 (3)C12—C131.366 (3)
O2—C11.184 (3)C12—H120.9300
C1—C21.452 (4)C13—C141.398 (3)
C2—C31.308 (3)C13—H130.9300
C2—H20.9300C14—C151.393 (4)
C3—C41.461 (3)C15—C161.371 (4)
C3—H30.9300C15—H150.9300
C4—C51.388 (3)C16—H160.9300
C4—C91.388 (4)C17—H17A0.9600
C5—C61.374 (3)C17—H17B0.9600
C5—H50.9300C17—H17C0.9600
C6—C71.368 (4)C18—H18A0.9600
C7—C81.376 (4)C18—H18B0.9600
C7—H70.9300C18—H18C0.9600
C8—C91.375 (3)
C10—N1—O1107.9 (2)N1—C10—H10119.0
C14—N2—C17122.0 (2)C11—C10—H10119.0
C14—N2—C18120.4 (2)C12—C11—C16117.0 (2)
C17—N2—C18117.6 (2)C12—C11—C10122.7 (2)
C1—O1—N1113.7 (2)C16—C11—C10120.3 (3)
O2—C1—O1124.3 (3)C13—C12—C11121.2 (3)
O2—C1—C2125.9 (3)C13—C12—H12119.4
O1—C1—C2109.8 (3)C11—C12—H12119.4
C3—C2—C1122.7 (3)C12—C13—C14122.2 (3)
C3—C2—H2118.7C12—C13—H13118.9
C1—C2—H2118.7C14—C13—H13118.9
C2—C3—C4128.7 (3)N2—C14—C15121.9 (2)
C2—C3—H3115.7N2—C14—C13121.8 (3)
C4—C3—H3115.7C15—C14—C13116.2 (2)
C5—C4—C9118.2 (2)C16—C15—C14120.9 (3)
C5—C4—C3119.2 (2)C16—C15—H15119.5
C9—C4—C3122.6 (2)C14—C15—H15119.5
C6—C5—C4120.5 (3)C15—C16—C11122.4 (3)
C6—C5—H5119.8C15—C16—H16118.8
C4—C5—H5119.8C11—C16—H16118.8
C7—C6—C5120.8 (3)N2—C17—H17A109.5
C7—C6—Cl1120.2 (2)N2—C17—H17B109.5
C5—C6—Cl1119.0 (2)H17A—C17—H17B109.5
C6—C7—C8119.4 (2)N2—C17—H17C109.5
C6—C7—H7120.3H17A—C17—H17C109.5
C8—C7—H7120.3H17B—C17—H17C109.5
C9—C8—C7120.2 (3)N2—C18—H18A109.5
C9—C8—H8119.9N2—C18—H18B109.5
C7—C8—H8119.9H18A—C18—H18B109.5
C8—C9—C4120.9 (3)N2—C18—H18C109.5
C8—C9—H9119.6H18A—C18—H18C109.5
C4—C9—H9119.6H18B—C18—H18C109.5
N1—C10—C11122.0 (3)
C10—N1—O1—C1176.4 (2)O1—N1—C10—C11179.6 (2)
N1—O1—C1—O20.4 (4)N1—C10—C11—C122.3 (4)
N1—O1—C1—C2179.5 (2)N1—C10—C11—C16176.8 (3)
O2—C1—C2—C31.6 (5)C16—C11—C12—C130.2 (4)
O1—C1—C2—C3178.3 (3)C10—C11—C12—C13178.8 (3)
C1—C2—C3—C4178.4 (3)C11—C12—C13—C140.0 (5)
C2—C3—C4—C5175.2 (3)C17—N2—C14—C15178.6 (3)
C2—C3—C4—C94.2 (5)C18—N2—C14—C153.2 (4)
C9—C4—C5—C60.7 (4)C17—N2—C14—C130.9 (4)
C3—C4—C5—C6178.8 (2)C18—N2—C14—C13177.3 (3)
C4—C5—C6—C70.4 (4)C12—C13—C14—N2179.6 (3)
C4—C5—C6—Cl1178.5 (2)C12—C13—C14—C150.0 (4)
C5—C6—C7—C80.6 (4)N2—C14—C15—C16179.8 (3)
Cl1—C6—C7—C8179.5 (2)C13—C14—C15—C160.2 (4)
C6—C7—C8—C91.3 (5)C14—C15—C16—C110.5 (5)
C7—C8—C9—C41.0 (5)C12—C11—C16—C150.5 (4)
C5—C4—C9—C80.0 (4)C10—C11—C16—C15178.6 (3)
C3—C4—C9—C8179.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O2i0.932.643.292 (3)128
C8—H8···N1i0.932.833.735 (4)164
Symmetry code: (i) x, y1, z.
 

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