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In the title compound, C21H21Cl2N3O3, the dihedral angle between the benzene rings is 81.1 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031028/bv6032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031028/bv6032Isup2.hkl
Contains datablock I

CCDC reference: 289666

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.042
  • wR factor = 0.118
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

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

(E,E,E)-2-(2-{[3-(2,6-Dichlorophenyl)-1-methyl-trans-2- propenylidene]aminooxymethyl}phenyl)-2-methoxyimino-N-methylacetamide top
Crystal data top
C21H21Cl2N3O3F(000) = 904
Mr = 434.31Dx = 1.379 Mg m3
Monoclinic, P21/cMelting point: 404 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.2864 (14) ÅCell parameters from 4514 reflections
b = 14.469 (2) Åθ = 2.7–26.3°
c = 17.703 (3) ŵ = 0.34 mm1
β = 99.681 (3)°T = 294 K
V = 2092.3 (6) Å3Prism, colourless
Z = 40.16 × 0.12 × 0.04 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4309 independent reflections
Radiation source: fine-focus sealed tube3090 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 810
Tmin = 0.940, Tmax = 0.987k = 1818
11730 measured reflectionsl = 1422
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.879P]
where P = (Fo2 + 2Fc2)/3
4309 reflections(Δ/σ)max = 0.001
269 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.37 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
Cl11.38842 (8)0.37991 (5)0.05146 (4)0.0712 (2)
Cl20.74307 (8)0.35734 (6)0.07856 (3)0.0739 (2)
O10.74132 (17)0.32583 (9)0.26500 (7)0.0449 (3)
O20.68292 (18)0.41480 (13)0.47994 (9)0.0618 (4)
O31.05890 (19)0.48821 (13)0.32940 (10)0.0701 (5)
N10.7506 (2)0.35608 (11)0.19011 (9)0.0428 (4)
N20.8384 (2)0.40239 (13)0.46230 (10)0.0480 (4)
N31.1187 (2)0.37263 (16)0.41428 (13)0.0615 (6)
H31.081 (3)0.3432 (18)0.4456 (16)0.065 (8)*
C11.0169 (3)0.2789 (2)0.21909 (14)0.0758 (8)
H1A0.99330.27570.27030.114*
H1B1.12010.30920.21970.114*
H1C1.02190.21750.19910.114*
C20.8864 (2)0.33153 (13)0.17012 (11)0.0414 (4)
C30.9040 (3)0.36044 (14)0.09338 (11)0.0443 (5)
H3A0.81820.39320.06490.053*
C41.0342 (3)0.34331 (14)0.06122 (11)0.0445 (5)
H41.11640.30880.09060.053*
C51.0662 (2)0.37150 (13)0.01457 (11)0.0415 (4)
C61.2274 (3)0.38861 (15)0.02563 (12)0.0477 (5)
C71.2670 (3)0.41332 (16)0.09542 (14)0.0575 (6)
H71.37560.42390.10010.069*
C81.1458 (3)0.42216 (16)0.15774 (13)0.0582 (6)
H81.17190.43860.20500.070*
C90.9859 (3)0.40677 (16)0.15056 (12)0.0554 (6)
H90.90320.41370.19270.067*
C100.9480 (3)0.38103 (14)0.08070 (12)0.0472 (5)
C110.5970 (2)0.36369 (13)0.28717 (12)0.0426 (5)
H11A0.57810.33340.33380.051*
H11B0.50420.35040.24750.051*
C120.6064 (2)0.46627 (13)0.30049 (10)0.0355 (4)
C130.7296 (2)0.50431 (13)0.35461 (10)0.0354 (4)
C140.7353 (3)0.59863 (14)0.36618 (11)0.0444 (5)
H140.81900.62420.40160.053*
C150.6179 (3)0.65526 (14)0.32558 (12)0.0486 (5)
H150.62190.71870.33420.058*
C160.4953 (3)0.61839 (15)0.27271 (12)0.0492 (5)
H160.41550.65660.24570.059*
C170.4905 (2)0.52443 (14)0.25967 (11)0.0436 (5)
H170.40840.49970.22290.052*
C180.8554 (2)0.44515 (13)0.40118 (10)0.0387 (4)
C190.6732 (3)0.3681 (2)0.55059 (14)0.0767 (8)
H19A0.67460.30250.54260.115*
H19B0.57350.38510.56780.115*
H19C0.76500.38540.58860.115*
C201.0211 (2)0.43733 (16)0.37813 (12)0.0474 (5)
C211.2856 (3)0.3594 (2)0.40305 (19)0.0868 (9)
H21A1.28640.33310.35330.130*
H21B1.34040.31840.44170.130*
H21C1.34100.41790.40660.130*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0533 (4)0.0961 (5)0.0634 (4)0.0003 (3)0.0072 (3)0.0153 (3)
Cl20.0539 (4)0.1191 (6)0.0468 (3)0.0006 (3)0.0036 (3)0.0024 (3)
O10.0541 (8)0.0460 (8)0.0384 (7)0.0059 (6)0.0188 (6)0.0030 (6)
O20.0448 (8)0.0964 (13)0.0481 (9)0.0046 (8)0.0188 (7)0.0238 (8)
O30.0485 (9)0.0954 (13)0.0708 (11)0.0000 (9)0.0229 (8)0.0328 (10)
N10.0488 (10)0.0471 (9)0.0335 (8)0.0038 (8)0.0104 (7)0.0008 (7)
N20.0378 (9)0.0647 (11)0.0421 (9)0.0025 (8)0.0087 (7)0.0119 (8)
N30.0398 (10)0.0847 (15)0.0620 (13)0.0105 (10)0.0143 (9)0.0220 (12)
C10.0791 (17)0.104 (2)0.0498 (13)0.0467 (16)0.0271 (13)0.0247 (14)
C20.0492 (11)0.0394 (10)0.0368 (10)0.0061 (9)0.0105 (9)0.0010 (8)
C30.0513 (12)0.0454 (11)0.0369 (10)0.0107 (9)0.0095 (9)0.0013 (9)
C40.0522 (12)0.0445 (11)0.0377 (10)0.0071 (9)0.0100 (9)0.0038 (9)
C50.0514 (12)0.0387 (10)0.0363 (10)0.0063 (9)0.0131 (9)0.0005 (8)
C60.0541 (13)0.0464 (12)0.0443 (11)0.0042 (10)0.0129 (10)0.0030 (9)
C70.0649 (15)0.0571 (14)0.0557 (14)0.0025 (11)0.0258 (12)0.0048 (11)
C80.0867 (18)0.0534 (13)0.0402 (12)0.0017 (12)0.0270 (12)0.0036 (10)
C90.0757 (16)0.0555 (13)0.0355 (11)0.0079 (12)0.0106 (11)0.0010 (10)
C100.0550 (13)0.0483 (12)0.0397 (11)0.0063 (10)0.0116 (9)0.0021 (9)
C110.0411 (11)0.0457 (11)0.0435 (11)0.0044 (9)0.0146 (9)0.0037 (9)
C120.0329 (9)0.0436 (10)0.0324 (9)0.0027 (8)0.0122 (7)0.0002 (8)
C130.0333 (9)0.0445 (11)0.0305 (9)0.0028 (8)0.0111 (7)0.0034 (8)
C140.0481 (11)0.0481 (12)0.0371 (10)0.0093 (9)0.0075 (9)0.0011 (9)
C150.0597 (13)0.0390 (11)0.0494 (12)0.0014 (10)0.0161 (10)0.0008 (9)
C160.0489 (12)0.0532 (13)0.0455 (12)0.0087 (10)0.0077 (10)0.0087 (10)
C170.0379 (10)0.0546 (12)0.0374 (10)0.0019 (9)0.0040 (8)0.0011 (9)
C180.0361 (10)0.0465 (11)0.0337 (9)0.0043 (8)0.0065 (8)0.0039 (8)
C190.0707 (17)0.114 (2)0.0498 (14)0.0126 (15)0.0235 (13)0.0267 (15)
C200.0358 (10)0.0653 (14)0.0412 (11)0.0027 (10)0.0066 (9)0.0081 (10)
C210.0443 (14)0.124 (3)0.094 (2)0.0202 (15)0.0161 (14)0.0232 (19)
Geometric parameters (Å, º) top
Cl1—C61.745 (2)C8—C91.370 (3)
Cl2—C101.739 (2)C8—H80.9300
O1—N11.410 (2)C9—C101.377 (3)
O1—C111.429 (2)C9—H90.9300
O2—N21.388 (2)C11—C121.503 (3)
O2—C191.436 (3)C11—H11A0.9700
O3—C201.215 (3)C11—H11B0.9700
N1—C21.286 (2)C12—C171.385 (3)
N2—C181.275 (2)C12—C131.391 (3)
N3—C201.329 (3)C13—C141.380 (3)
N3—C211.443 (3)C13—C181.487 (3)
N3—H30.80 (3)C14—C151.378 (3)
C1—C21.478 (3)C14—H140.9300
C1—H1A0.9600C15—C161.368 (3)
C1—H1B0.9600C15—H150.9300
C1—H1C0.9600C16—C171.378 (3)
C2—C31.452 (3)C16—H160.9300
C3—C41.325 (3)C17—H170.9300
C3—H3A0.9300C18—C201.501 (3)
C4—C51.468 (3)C19—H19A0.9600
C4—H40.9300C19—H19B0.9600
C5—C101.401 (3)C19—H19C0.9600
C5—C61.404 (3)C21—H21A0.9600
C6—C71.378 (3)C21—H21B0.9600
C7—C81.368 (3)C21—H21C0.9600
C7—H70.9300
N1—O1—C11108.64 (14)O1—C11—H11A108.9
N2—O2—C19108.99 (17)C12—C11—H11A108.9
C2—N1—O1111.20 (15)O1—C11—H11B108.9
C18—N2—O2111.56 (16)C12—C11—H11B108.9
C20—N3—C21123.1 (2)H11A—C11—H11B107.7
C20—N3—H3115.5 (19)C17—C12—C13118.88 (18)
C21—N3—H3121.2 (19)C17—C12—C11120.35 (17)
C2—C1—H1A109.5C13—C12—C11120.76 (17)
C2—C1—H1B109.5C14—C13—C12119.79 (18)
H1A—C1—H1B109.5C14—C13—C18118.93 (17)
C2—C1—H1C109.5C12—C13—C18121.28 (17)
H1A—C1—H1C109.5C15—C14—C13120.46 (19)
H1B—C1—H1C109.5C15—C14—H14119.8
N1—C2—C3114.10 (17)C13—C14—H14119.8
N1—C2—C1124.66 (18)C16—C15—C14120.2 (2)
C3—C2—C1121.24 (18)C16—C15—H15119.9
C4—C3—C2124.42 (19)C14—C15—H15119.9
C4—C3—H3A117.8C15—C16—C17119.7 (2)
C2—C3—H3A117.8C15—C16—H16120.1
C3—C4—C5128.73 (19)C17—C16—H16120.1
C3—C4—H4115.6C16—C17—C12120.94 (19)
C5—C4—H4115.6C16—C17—H17119.5
C10—C5—C6114.45 (18)C12—C17—H17119.5
C10—C5—C4125.62 (19)N2—C18—C13125.67 (17)
C6—C5—C4119.90 (18)N2—C18—C20115.51 (17)
C7—C6—C5123.1 (2)C13—C18—C20118.75 (16)
C7—C6—Cl1116.99 (18)O2—C19—H19A109.5
C5—C6—Cl1119.88 (16)O2—C19—H19B109.5
C8—C7—C6119.6 (2)H19A—C19—H19B109.5
C8—C7—H7120.2O2—C19—H19C109.5
C6—C7—H7120.2H19A—C19—H19C109.5
C7—C8—C9120.0 (2)H19B—C19—H19C109.5
C7—C8—H8120.0O3—C20—N3124.1 (2)
C9—C8—H8120.0O3—C20—C18120.29 (19)
C8—C9—C10119.8 (2)N3—C20—C18115.64 (18)
C8—C9—H9120.1N3—C21—H21A109.5
C10—C9—H9120.1N3—C21—H21B109.5
C9—C10—C5123.0 (2)H21A—C21—H21B109.5
C9—C10—Cl2116.33 (18)N3—C21—H21C109.5
C5—C10—Cl2120.69 (16)H21A—C21—H21C109.5
O1—C11—C12113.47 (15)H21B—C21—H21C109.5
C11—O1—N1—C2173.60 (16)O1—C11—C12—C1358.3 (2)
C19—O2—N2—C18177.9 (2)C17—C12—C13—C140.6 (3)
O1—N1—C2—C3179.94 (15)C11—C12—C13—C14179.67 (17)
O1—N1—C2—C10.3 (3)C17—C12—C13—C18178.84 (17)
N1—C2—C3—C4179.5 (2)C11—C12—C13—C180.2 (3)
C1—C2—C3—C40.3 (3)C12—C13—C14—C151.3 (3)
C2—C3—C4—C5178.1 (2)C18—C13—C14—C15178.12 (18)
C3—C4—C5—C1033.4 (3)C13—C14—C15—C160.7 (3)
C3—C4—C5—C6148.6 (2)C14—C15—C16—C170.6 (3)
C10—C5—C6—C70.4 (3)C15—C16—C17—C121.3 (3)
C4—C5—C6—C7178.6 (2)C13—C12—C17—C160.7 (3)
C10—C5—C6—Cl1179.78 (15)C11—C12—C17—C16178.33 (18)
C4—C5—C6—Cl12.1 (3)O2—N2—C18—C132.1 (3)
C5—C6—C7—C80.1 (3)O2—N2—C18—C20178.88 (17)
Cl1—C6—C7—C8179.33 (18)C14—C13—C18—N296.3 (2)
C6—C7—C8—C90.2 (4)C12—C13—C18—N283.2 (3)
C7—C8—C9—C101.0 (3)C14—C13—C18—C2080.4 (2)
C8—C9—C10—C51.5 (3)C12—C13—C18—C20100.2 (2)
C8—C9—C10—Cl2176.81 (18)C21—N3—C20—O34.1 (4)
C6—C5—C10—C91.2 (3)C21—N3—C20—C18175.8 (2)
C4—C5—C10—C9179.2 (2)N2—C18—C20—O3166.7 (2)
C6—C5—C10—Cl2177.06 (15)C13—C18—C20—O310.3 (3)
C4—C5—C10—Cl21.0 (3)N2—C18—C20—N313.2 (3)
N1—O1—C11—C1270.10 (19)C13—C18—C20—N3169.74 (19)
O1—C11—C12—C17122.63 (19)
 

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