Literature DB >> 21581035

3,4-Dimeth-oxy-N-(3-nitro-benzyl-idene)aniline.

Mehmet Akkurt, Ali Asghar Jarrahpour, Malihe Aye, Mustafa Gençaslan, Orhan Büyükgüngör.   

Abstract

The title compound, C(15)H(14)N(2)O(4), has two crystallographically independent mol-ecules in the asymmetric unit. In both mol-ecules, the nitro and the two meth-oxy substituents are coplanar with the benzene rings to which they are attached. The benzene rings are nearly coplanar, with dihedral angles between the two benzene rings of 10.39 (8) and 5.95 (8)° in the two mol-ecules. The two independent mol-ecules in the asymmetric unit are rotated with respect to each other such that the dihedral angles between equivalent benzene rings are 49.11 (8) and 63.93 (8)°. In the crystal structure, inter-molecular C-H⋯O hydrogen-bond contacts and a weak C-H⋯π inter-action are observed.

Entities:  

Year:  2008        PMID： 21581035      PMCID： PMC2959659          DOI： 10.1107/S1600536808034193

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background, see: Arora et al. (2002 ▶); Desai et al. (2001 ▶); El-masry et al. (2000 ▶); Jarrahpour & Khalili (2006 ▶); Jarrahpour et al. (2004 ▶); More et al. (2001 ▶); Phatak et al. (2000 ▶); Samadhiya & Halve (2001 ▶); Singh & Dash (1988 ▶); Tanaka & Shiraishi (2000 ▶). For related structures, see: Akkurt et al. (2005 ▶, 2008 ▶).

Experimental

Crystal data

C15H14N2O4 M = 286.28 Triclinic, a = 8.6345 (8) Å b = 8.6540 (8) Å c = 19.2304 (17) Å α = 96.629 (7)° β = 97.338 (7)° γ = 102.075 (7)° V = 1378.6 (2) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 296 K 0.78 × 0.36 × 0.07 mm

Data collection

Stoe IPDS II diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.925, T max = 0.993 21166 measured reflections 6330 independent reflections 3703 reflections with I > 2σ(I) R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.119 S = 0.98 6330 reflections 380 parameters H-atom parameters constrained Δρmax = 0.15 e Å−3 Δρmin = −0.13 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034193/ez2145sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034193/ez2145Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H14N2O4Z = 4
Mr = 286.28F(000) = 600
Triclinic, P1Dx = 1.379 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6345 (8) ÅCell parameters from 17758 reflections
b = 8.6540 (8) Åθ = 2.2–28.0°
c = 19.2304 (17) ŵ = 0.10 mm−1
α = 96.629 (7)°T = 296 K
β = 97.338 (7)°Plate, yellow
γ = 102.075 (7)°0.78 × 0.36 × 0.07 mm
V = 1378.6 (2) Å3
Stoe IPDS II diffractometer6330 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3703 reflections with I > 2σ(I)
plane graphiteRint = 0.065
Detector resolution: 6.67 pixels mm-1θmax = 27.6°, θmin = 2.2°
ω scansh = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −11→11
Tmin = 0.925, Tmax = 0.993l = −24→24
21166 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.119w = 1/[σ2(Fo2) + (0.0559P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
6330 reflectionsΔρmax = 0.15 e Å−3
380 parametersΔρmin = −0.13 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001Fc2λ3/sin(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0065 (13)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
O10.62826 (14)0.32088 (17)−0.08996 (7)0.0729 (5)
O20.49739 (15)0.47609 (18)−0.17819 (7)0.0779 (5)
O3−0.37252 (16)0.1054 (2)0.11097 (9)0.0897 (6)
O4−0.39393 (17)−0.0126 (2)0.20230 (8)0.0972 (6)
N10.14725 (16)0.23760 (17)0.02524 (8)0.0601 (5)
N2−0.31661 (18)0.04278 (19)0.15877 (9)0.0664 (6)
C10.24228 (19)0.3003 (2)−0.02440 (9)0.0560 (6)
C20.39725 (19)0.2781 (2)−0.02885 (9)0.0572 (6)
C30.47868 (19)0.3383 (2)−0.08055 (9)0.0568 (6)
C40.4075 (2)0.4223 (2)−0.12873 (9)0.0586 (6)
C50.2561 (2)0.4444 (2)−0.12409 (10)0.0667 (7)
C60.1746 (2)0.3826 (2)−0.07202 (10)0.0644 (6)
C70.7050 (2)0.2369 (3)−0.04221 (11)0.0732 (7)
C80.4271 (3)0.5528 (3)−0.23003 (13)0.0983 (10)
C90.2050 (2)0.1789 (2)0.07672 (10)0.0599 (6)
C100.10483 (19)0.1058 (2)0.12568 (9)0.0536 (6)
C11−0.05710 (19)0.10691 (19)0.11873 (9)0.0525 (5)
C12−0.14762 (19)0.03390 (19)0.16476 (9)0.0529 (5)
C13−0.0856 (2)−0.0437 (2)0.21671 (9)0.0604 (6)
C140.0736 (2)−0.0444 (2)0.22346 (10)0.0675 (7)
C150.1685 (2)0.0304 (2)0.17885 (10)0.0630 (6)
O50.06734 (14)0.60630 (14)0.26497 (6)0.0629 (4)
O6−0.07174 (16)0.73981 (14)0.35747 (7)0.0704 (5)
O7−0.4307 (2)−0.31605 (19)0.63291 (10)0.1093 (7)
O8−0.3373 (2)−0.29259 (17)0.53686 (9)0.0982 (7)
N3−0.19109 (17)0.23924 (16)0.45961 (7)0.0581 (5)
N4−0.38348 (19)−0.23626 (19)0.58865 (9)0.0690 (6)
C16−0.1260 (2)0.33841 (18)0.41193 (9)0.0528 (5)
C17−0.0490 (2)0.2699 (2)0.36272 (10)0.0694 (7)
C180.0180 (2)0.3553 (2)0.31274 (10)0.0655 (7)
C190.00864 (19)0.51125 (19)0.31179 (8)0.0516 (5)
C20−0.06863 (19)0.58383 (18)0.36230 (9)0.0505 (5)
C21−0.13542 (19)0.49789 (19)0.41131 (9)0.0526 (5)
C220.1519 (3)0.5404 (2)0.21425 (11)0.0764 (8)
C23−0.1356 (3)0.8214 (2)0.41150 (12)0.0798 (8)
C24−0.2518 (2)0.2938 (2)0.51111 (9)0.0558 (6)
C25−0.31981 (19)0.18957 (19)0.56009 (9)0.0526 (5)
C26−0.31842 (19)0.02855 (19)0.55182 (9)0.0538 (5)
C27−0.38451 (19)−0.0654 (2)0.59839 (9)0.0537 (5)
C28−0.4530 (2)−0.0053 (2)0.65350 (9)0.0631 (7)
C29−0.4539 (2)0.1540 (2)0.66146 (10)0.0702 (7)
C30−0.3882 (2)0.2513 (2)0.61519 (10)0.0633 (6)
H20.445100.222700.003100.0690*
H50.208200.50050−0.155700.0800*
H60.071800.39750−0.069400.0770*
H7A0.808900.23260−0.054000.1100*
H7B0.641500.13030−0.045600.1100*
H7C0.716500.290900.005300.1100*
H8A0.502100.58450−0.261400.1470*
H8B0.398600.64560−0.207600.1470*
H8C0.332700.48090−0.256600.1470*
H90.314200.181900.083900.0720*
H11−0.103400.156100.083600.0630*
H13−0.15050−0.094100.246300.0730*
H140.11830−0.095400.258200.0810*
H150.277100.030200.184500.0760*
H17−0.041500.164300.362800.0830*
H180.069300.306500.279800.0790*
H21−0.187200.546100.444300.0630*
H22A0.187300.618500.184600.1150*
H22B0.082200.447700.185600.1150*
H22C0.243200.510800.238500.1150*
H23A−0.131700.929100.402800.1200*
H23B−0.073400.822700.456700.1200*
H23C−0.244800.767600.411400.1200*
H24−0.253300.401600.518000.0670*
H26−0.27330−0.015500.515200.0650*
H28−0.49730−0.071000.684300.0760*
H29−0.499100.197300.698300.0840*
H30−0.390200.359000.621200.0760*
U11U22U33U12U13U23
O10.0571 (7)0.1085 (10)0.0671 (8)0.0268 (7)0.0286 (6)0.0354 (7)
O20.0699 (8)0.1108 (11)0.0679 (8)0.0238 (7)0.0317 (7)0.0455 (8)
O30.0671 (8)0.1186 (12)0.1004 (12)0.0323 (8)0.0288 (8)0.0475 (10)
O40.0799 (9)0.1330 (13)0.0907 (11)0.0167 (9)0.0519 (9)0.0366 (10)
N10.0573 (8)0.0702 (9)0.0606 (9)0.0152 (7)0.0256 (7)0.0221 (7)
N20.0637 (9)0.0753 (10)0.0642 (10)0.0117 (8)0.0301 (8)0.0121 (8)
C10.0561 (9)0.0598 (10)0.0555 (10)0.0099 (8)0.0216 (8)0.0144 (8)
C20.0560 (9)0.0682 (11)0.0539 (10)0.0155 (8)0.0205 (8)0.0195 (8)
C30.0518 (9)0.0680 (11)0.0534 (10)0.0112 (8)0.0188 (8)0.0132 (8)
C40.0571 (9)0.0697 (11)0.0524 (10)0.0097 (8)0.0209 (8)0.0179 (8)
C50.0624 (11)0.0797 (12)0.0653 (12)0.0183 (9)0.0176 (9)0.0284 (10)
C60.0529 (9)0.0805 (12)0.0681 (12)0.0178 (9)0.0230 (9)0.0253 (10)
C70.0606 (11)0.0953 (14)0.0749 (13)0.0283 (10)0.0218 (10)0.0271 (11)
C80.0993 (16)0.142 (2)0.0828 (16)0.0479 (15)0.0419 (13)0.0677 (16)
C90.0525 (9)0.0718 (11)0.0608 (11)0.0147 (8)0.0211 (8)0.0171 (9)
C100.0560 (9)0.0566 (10)0.0512 (10)0.0128 (7)0.0181 (8)0.0098 (7)
C110.0573 (9)0.0574 (10)0.0468 (9)0.0136 (7)0.0173 (7)0.0134 (7)
C120.0574 (9)0.0535 (9)0.0502 (9)0.0100 (7)0.0213 (8)0.0075 (7)
C130.0768 (12)0.0540 (10)0.0528 (10)0.0082 (8)0.0233 (9)0.0149 (8)
C140.0854 (13)0.0651 (11)0.0590 (11)0.0227 (9)0.0169 (10)0.0213 (9)
C150.0633 (10)0.0695 (11)0.0625 (11)0.0218 (9)0.0149 (9)0.0175 (9)
O50.0773 (8)0.0624 (7)0.0604 (7)0.0180 (6)0.0350 (6)0.0249 (6)
O60.1004 (9)0.0575 (7)0.0747 (8)0.0342 (7)0.0466 (7)0.0314 (6)
O70.1593 (15)0.0864 (10)0.1150 (13)0.0412 (10)0.0760 (12)0.0647 (10)
O80.1480 (14)0.0737 (9)0.0983 (12)0.0427 (9)0.0652 (11)0.0337 (8)
N30.0721 (9)0.0517 (8)0.0526 (8)0.0069 (7)0.0223 (7)0.0160 (6)
N40.0789 (10)0.0673 (10)0.0732 (11)0.0208 (8)0.0290 (9)0.0341 (8)
C160.0634 (10)0.0474 (9)0.0478 (9)0.0052 (7)0.0166 (8)0.0129 (7)
C170.1022 (14)0.0473 (10)0.0685 (12)0.0185 (9)0.0394 (11)0.0166 (8)
C180.0878 (13)0.0570 (10)0.0609 (11)0.0204 (9)0.0349 (10)0.0134 (8)
C190.0559 (9)0.0537 (9)0.0485 (9)0.0097 (7)0.0181 (8)0.0153 (7)
C200.0560 (9)0.0498 (9)0.0507 (9)0.0136 (7)0.0157 (7)0.0164 (7)
C210.0605 (9)0.0531 (9)0.0496 (9)0.0142 (7)0.0205 (8)0.0141 (7)
C220.0904 (13)0.0826 (13)0.0715 (13)0.0247 (11)0.0485 (11)0.0257 (10)
C230.1131 (16)0.0639 (11)0.0861 (14)0.0428 (11)0.0515 (13)0.0273 (10)
C240.0638 (10)0.0492 (9)0.0559 (10)0.0071 (7)0.0170 (8)0.0160 (8)
C250.0535 (9)0.0561 (10)0.0480 (9)0.0059 (7)0.0117 (7)0.0143 (7)
C260.0574 (9)0.0591 (10)0.0483 (9)0.0113 (8)0.0173 (8)0.0159 (8)
C270.0538 (9)0.0614 (10)0.0496 (9)0.0114 (7)0.0139 (7)0.0204 (8)
C280.0650 (10)0.0766 (13)0.0535 (11)0.0128 (9)0.0224 (9)0.0250 (9)
C290.0775 (12)0.0793 (13)0.0613 (12)0.0184 (10)0.0334 (10)0.0155 (10)
C300.0711 (11)0.0608 (11)0.0612 (11)0.0132 (9)0.0225 (9)0.0121 (9)
O1—C31.363 (2)C7—H7A0.9600
O1—C71.418 (3)C8—H8C0.9600
O2—C41.365 (2)C8—H8B0.9600
O2—C81.404 (3)C8—H8A0.9600
O3—N21.218 (2)C9—H90.9300
O4—N21.216 (2)C11—H110.9300
O5—C221.427 (3)C13—H130.9300
O5—C191.363 (2)C14—H140.9300
O6—C231.422 (3)C15—H150.9300
O6—C201.369 (2)C16—C171.373 (3)
O7—N41.214 (2)C16—C211.401 (2)
O8—N41.208 (2)C17—C181.390 (3)
N1—C11.419 (2)C18—C191.371 (2)
N1—C91.258 (2)C19—C201.408 (2)
N2—C121.468 (2)C20—C211.377 (2)
N3—C241.268 (2)C24—C251.470 (2)
N3—C161.416 (2)C25—C261.387 (2)
N4—C271.471 (2)C25—C301.385 (2)
C1—C21.403 (2)C26—C271.376 (2)
C1—C61.369 (2)C27—C281.380 (2)
C2—C31.378 (2)C28—C291.371 (2)
C3—C41.401 (2)C29—C301.387 (3)
C4—C51.373 (3)C17—H170.9300
C5—C61.389 (3)C18—H180.9300
C9—C101.467 (2)C21—H210.9300
C10—C151.391 (2)C22—H22A0.9600
C10—C111.390 (2)C22—H22B0.9600
C11—C121.376 (2)C22—H22C0.9600
C12—C131.380 (2)C23—H23A0.9600
C13—C141.366 (3)C23—H23B0.9600
C14—C151.383 (3)C23—H23C0.9600
C2—H20.9300C24—H240.9300
C5—H50.9300C26—H260.9300
C6—H60.9300C28—H280.9300
C7—H7B0.9600C29—H290.9300
C7—H7C0.9600C30—H300.9300
O1···O22.575 (2)C21···H23B2.7600
O1···C22i3.410 (3)C22···H182.5300
O2···O12.575 (2)C23···H26v2.8400
O2···C22i3.220 (3)C23···H212.5000
O3···C7ii3.373 (3)C24···H212.6600
O4···C29iii3.322 (2)C28···H14xii3.0600
O4···C28iii3.222 (2)C29···H23Cxiii3.0400
O4···C3iv3.337 (2)H2···H7B2.2800
O5···C14v3.206 (2)H2···O3x2.8500
O5···C30vi3.285 (2)H2···C72.4900
O5···O62.5677 (18)H2···H7C2.2900
O6···O52.5677 (18)H2···H92.0600
O7···C8vii3.268 (3)H2···C92.6400
O8···C23viii3.274 (3)H5···C82.5100
O1···H22Ai2.6000H5···H8B2.2600
O2···H22Ci2.6400H5···O5ix2.8800
O3···H8Bix2.7400H5···H8C2.3400
O3···H9ii2.9100H6···H7Aii2.4900
O3···H112.4100H7A···H6x2.4900
O3···H7Biv2.8000H7B···H22.2800
O3···H2ii2.8500H7B···C22.7200
O3···H7Cii2.8200H7B···O3iv2.8000
O4···H28iii2.5700H7C···H11x2.5700
O4···H132.4400H7C···O3x2.8200
O4···H29iii2.7600H7C···C22.7300
O5···H14v2.5500H7C···H22.2900
O5···H5ix2.8800H7C···C5i2.9900
O6···H13v2.8000H7C···C6i2.8700
O7···H282.4400H8A···O7xi2.3900
O7···H30viii2.8900H8A···H22Ci2.5100
O7···H8Avii2.3900H8B···C52.7200
O8···H23Cviii2.7100H8B···H52.2600
O8···H24viii2.8800H8B···O3ix2.7400
O8···H21viii2.7500H8C···C19ix3.0200
O8···H262.4400H8C···C52.7500
N2···C2iv3.403 (2)H8C···H52.3400
N2···C3iv3.389 (2)H8C···C20ix2.7700
N4···C24iii3.380 (2)H9···H152.4800
N1···H112.5700H9···O3x2.9100
N3···H23Bvi2.8000H9···C22.5400
N3···H23Aviii2.9500H9···H22.0600
N3···H262.5700H11···C7ii2.9900
C2···N2iv3.403 (2)H11···H7Cii2.5700
C2···C3i3.594 (2)H11···O32.4100
C3···C2i3.594 (2)H11···N12.5700
C3···O4iv3.337 (2)H13···O6viii2.8000
C3···N2iv3.389 (2)H13···O42.4400
C7···O3x3.373 (3)H14···O5viii2.5500
C8···O7xi3.268 (3)H14···C28xii3.0600
C13···C183.598 (2)H15···H92.4800
C14···O5viii3.206 (2)H17···C133.0900
C18···C133.598 (2)H17···H23Aviii2.2800
C19···C30vi3.504 (2)H18···C133.0800
C20···C24vi3.341 (2)H18···C222.5300
C20···C25vi3.552 (2)H18···H22B2.3000
C21···C24vi3.498 (2)H18···H22C2.3500
C22···O2i3.220 (3)H21···O8v2.7500
C22···O1i3.410 (3)H21···C232.5000
C23···O8v3.274 (3)H21···C242.6600
C24···C21vi3.498 (2)H21···H23B2.3600
C24···C27iii3.599 (2)H21···H23C2.2200
C24···N4iii3.380 (2)H21···H242.0500
C24···C20vi3.341 (2)H22A···O1i2.6000
C25···C20vi3.552 (2)H22B···C113.0100
C25···C26iii3.582 (2)H22B···C182.7500
C26···C25iii3.582 (2)H22B···H182.3000
C26···C26iii3.403 (2)H22C···C182.7700
C27···C24iii3.599 (2)H22C···H182.3500
C28···O4iii3.222 (2)H22C···O2i2.6400
C29···O4iii3.322 (2)H22C···C8i3.0300
C30···C19vi3.504 (2)H22C···H8Ai2.5100
C30···O5vi3.285 (2)H23A···N3v2.9500
C2···H7C2.7300H23A···C17v3.1000
C2···H7B2.7200H23A···H17v2.2800
C2···H92.5400H23B···C212.7600
C5···H7Ci2.9900H23B···H212.3600
C5···H8B2.7200H23B···N3vi2.8000
C5···H8C2.7500H23C···O8v2.7100
C6···H7Ci2.8700H23C···C212.6900
C7···H22.4900H23C···H212.2200
C7···H11x2.9900H23C···C29xiii3.0400
C8···H52.5100H24···O8v2.8800
C8···H22Ci3.0300H24···C212.5500
C9···H22.6400H24···H212.0500
C11···H22B3.0100H24···H302.4600
C13···H173.0900H26···O82.4400
C13···H183.0800H26···N32.5700
C17···H23Aviii3.1000H26···C23viii2.8400
C18···H22C2.7700H28···O72.4400
C18···H22B2.7500H28···O4iii2.5700
C19···H8Cix3.0200H29···O4iii2.7600
C20···H8Cix2.7700H30···O7v2.8900
C21···H242.5500H30···H242.4600
C21···H23C2.6900
C3—O1—C7117.12 (14)C14—C13—H13121.00
C4—O2—C8117.65 (16)C12—C13—H13121.00
C19—O5—C22117.37 (13)C13—C14—H14120.00
C20—O6—C23116.66 (14)C15—C14—H14120.00
C1—N1—C9121.85 (15)C14—C15—H15119.00
O3—N2—O4123.16 (17)C10—C15—H15119.00
O4—N2—C12118.00 (16)N3—C16—C17116.25 (14)
O3—N2—C12118.84 (16)N3—C16—C21125.11 (15)
C16—N3—C24121.57 (14)C17—C16—C21118.65 (15)
O7—N4—O8122.33 (17)C16—C17—C18121.30 (16)
O7—N4—C27118.52 (16)C17—C18—C19120.26 (16)
O8—N4—C27119.14 (16)O5—C19—C18125.71 (15)
N1—C1—C2124.00 (15)O5—C19—C20115.11 (14)
N1—C1—C6117.13 (15)C18—C19—C20119.18 (15)
C2—C1—C6118.83 (16)O6—C20—C19115.11 (14)
C1—C2—C3120.08 (16)O6—C20—C21124.80 (15)
O1—C3—C2124.52 (16)C19—C20—C21120.09 (15)
C2—C3—C4120.24 (16)C16—C21—C20120.52 (16)
O1—C3—C4115.23 (15)N3—C24—C25121.11 (15)
O2—C4—C3115.77 (15)C24—C25—C26121.08 (15)
C3—C4—C5119.56 (16)C24—C25—C30120.06 (15)
O2—C4—C5124.67 (16)C26—C25—C30118.85 (16)
C4—C5—C6119.80 (17)C25—C26—C27119.36 (16)
C1—C6—C5121.48 (16)N4—C27—C26118.80 (15)
N1—C9—C10121.83 (16)N4—C27—C28118.86 (15)
C11—C10—C15118.52 (16)C26—C27—C28122.34 (16)
C9—C10—C11120.57 (15)C27—C28—C29118.05 (16)
C9—C10—C15120.89 (16)C28—C29—C30120.76 (17)
C10—C11—C12118.74 (16)C25—C30—C29120.65 (16)
C11—C12—C13122.91 (16)C16—C17—H17119.00
N2—C12—C11117.96 (15)C18—C17—H17119.00
N2—C12—C13119.11 (15)C17—C18—H18120.00
C12—C13—C14118.19 (16)C19—C18—H18120.00
C13—C14—C15120.30 (17)C16—C21—H21120.00
C10—C15—C14121.31 (16)C20—C21—H21120.00
C3—C2—H2120.00O5—C22—H22A109.00
C1—C2—H2120.00O5—C22—H22B109.00
C4—C5—H5120.00O5—C22—H22C109.00
C6—C5—H5120.00H22A—C22—H22B110.00
C5—C6—H6119.00H22A—C22—H22C109.00
C1—C6—H6119.00H22B—C22—H22C109.00
O1—C7—H7C109.00O6—C23—H23A109.00
O1—C7—H7A109.00O6—C23—H23B109.00
O1—C7—H7B109.00O6—C23—H23C110.00
H7B—C7—H7C109.00H23A—C23—H23B109.00
H7A—C7—H7B109.00H23A—C23—H23C109.00
H7A—C7—H7C110.00H23B—C23—H23C109.00
O2—C8—H8A109.00N3—C24—H24119.00
O2—C8—H8C109.00C25—C24—H24119.00
H8A—C8—H8B109.00C25—C26—H26120.00
O2—C8—H8B110.00C27—C26—H26120.00
H8B—C8—H8C109.00C27—C28—H28121.00
H8A—C8—H8C109.00C29—C28—H28121.00
N1—C9—H9119.00C28—C29—H29120.00
C10—C9—H9119.00C30—C29—H29120.00
C10—C11—H11121.00C25—C30—H30120.00
C12—C11—H11121.00C29—C30—H30120.00
C7—O1—C3—C2−1.0 (3)N1—C9—C10—C15174.86 (17)
C7—O1—C3—C4179.84 (17)C11—C10—C15—C141.0 (3)
C8—O2—C4—C5−3.2 (3)C9—C10—C15—C14−177.38 (17)
C8—O2—C4—C3176.40 (17)C15—C10—C11—C120.2 (2)
C22—O5—C19—C18−2.8 (2)C9—C10—C11—C12178.56 (16)
C22—O5—C19—C20177.79 (16)C10—C11—C12—C13−1.5 (3)
C23—O6—C20—C216.2 (3)C10—C11—C12—N2177.18 (15)
C23—O6—C20—C19−174.41 (17)N2—C12—C13—C14−177.09 (16)
C1—N1—C9—C10−176.43 (16)C11—C12—C13—C141.5 (3)
C9—N1—C1—C6−170.48 (17)C12—C13—C14—C15−0.3 (3)
C9—N1—C1—C211.8 (3)C13—C14—C15—C10−0.9 (3)
O4—N2—C12—C133.4 (2)C17—C16—C21—C200.0 (3)
O3—N2—C12—C13−176.91 (17)C21—C16—C17—C18−0.4 (3)
O3—N2—C12—C114.4 (2)N3—C16—C21—C20−179.64 (16)
O4—N2—C12—C11−175.31 (17)N3—C16—C17—C18179.29 (16)
C24—N3—C16—C21−6.9 (3)C16—C17—C18—C190.2 (3)
C16—N3—C24—C25179.68 (16)C17—C18—C19—C200.4 (3)
C24—N3—C16—C17173.53 (17)C17—C18—C19—O5−178.99 (16)
O8—N4—C27—C28173.22 (18)C18—C19—C20—O6179.79 (15)
O7—N4—C27—C28−6.1 (3)O5—C19—C20—C21178.67 (15)
O7—N4—C27—C26174.45 (18)O5—C19—C20—O6−0.7 (2)
O8—N4—C27—C26−6.2 (3)C18—C19—C20—C21−0.8 (3)
N1—C1—C6—C5−178.02 (16)C19—C20—C21—C160.6 (3)
C6—C1—C2—C3−0.1 (3)O6—C20—C21—C16179.96 (15)
N1—C1—C2—C3177.54 (16)N3—C24—C25—C260.6 (3)
C2—C1—C6—C5−0.2 (3)N3—C24—C25—C30−178.79 (17)
C1—C2—C3—O1−178.89 (16)C24—C25—C26—C27−179.43 (16)
C1—C2—C3—C40.2 (3)C30—C25—C26—C27−0.1 (2)
C2—C3—C4—O2−179.55 (16)C26—C25—C30—C290.2 (3)
O1—C3—C4—O2−0.4 (2)C24—C25—C30—C29179.50 (16)
C2—C3—C4—C50.1 (3)C25—C26—C27—N4179.48 (16)
O1—C3—C4—C5179.23 (16)C25—C26—C27—C280.1 (3)
O2—C4—C5—C6179.20 (17)N4—C27—C28—C29−179.54 (16)
C3—C4—C5—C6−0.4 (3)C26—C27—C28—C29−0.1 (3)
C4—C5—C6—C10.5 (3)C27—C28—C29—C300.2 (3)
N1—C9—C10—C11−3.5 (3)C28—C29—C30—C25−0.2 (3)
D—H···AD—HH···AD···AD—H···A
C8—H8A···O7xi0.962.393.268 (3)152
C14—H14···O5viii0.932.553.206 (2)128
C22—H22A···O1i0.962.603.410 (3)143
C28—H28···O4iii0.932.573.222 (2)128
C18—H18···Cg10.932.893.654 (2)141
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C8—H8A⋯O7i0.962.393.268 (3)152
C14—H14⋯O5ii0.932.553.206 (2)128
C22—H22A⋯O1iii0.962.603.410 (3)143
C28—H28⋯O4iv0.932.573.222 (2)128
C18—H18⋯Cg10.932.893.654 (2)141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C10–C15 ring.

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Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Authors:  A A Jarrahpour; M Motamedifar; K Pakshir; N Hadi; M Zarei
Journal:  Molecules       Date:  2004-09-30       Impact factor: 4.411

3.  Synthesis of some new bis-Schiff bases of isatin and 5-fluoroisatin in a water suspension medium.

Authors:  A A Jarrahpour; D Khalili
Journal:  Molecules       Date:  2006-01-31       Impact factor: 4.411

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-09
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1.  4-Chloro-N-(3,4,5-trimethoxy-benzyl-idene)aniline.

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