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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2355.
Published online 2010 August 18. doi:  10.1107/S1600536810032782
PMCID: PMC3008132

4-Chloro-N-[(E)-(3,4-dimeth­oxy­phen­yl)methyl­idene]aniline

Abstract

The asymmetric unit of the title compound, C15H14ClNO2, contains two mol­ecules with significantly different conformations: the dihedral angles between the 4-chloro­aniline and 3,4-dimeth­oxy­phenyl (excluding C atoms) moieties are 19.68 (7) and 45.54 (4)°. In the crystal, the mol­ecules are linked by C—H(...)O hydrogen bonds and weak C—H(...)π inter­actions.

Related literature

For related structures, see: Dehno Khalaji et al. (2009 [triangle]); Shang & Tan (2007 [triangle]).

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Object name is e-66-o2355-scheme1.jpg

Experimental

Crystal data

  • C15H14ClNO2
  • M r = 275.72
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2355-efi1.jpg
  • a = 12.4227 (4) Å
  • b = 7.3638 (2) Å
  • c = 30.4583 (13) Å
  • β = 96.080 (2)°
  • V = 2770.60 (17) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 296 K
  • 0.35 × 0.22 × 0.20 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.932, T max = 0.950
  • 20975 measured reflections
  • 5007 independent reflections
  • 3456 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.120
  • S = 1.05
  • 5007 reflections
  • 347 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032782/hb5610sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032782/hb5610Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The crystal structures of (II) i.e, 4-chloro-N-(3,4,5-trimethoxybenzylidene)aniline (Dehno Khalaji et al., 2009) and (III) i.e, 4-[(4-chlorophenyl)iminomethyl]-2-methoxyphenol (Shang & Tan, 2007) have been published which are related to the title compound (I, Fig. 1)

The title compound consists of two molecules in the crystallographic asymmetric unit which differ from each other geometrically. In one molecule, the 4-chloroanilinic group A (C1—C6/N1/CL1) and group B (C7—C13/O1/O2) of 3,4-dimethoxyphenyl are planar with r.m.s. deviation of 0.0081 and 0.0146 Å, respectively. The dihedral angle between A/B is 45.54 (4)°. The C-atoms C14 and C15 of 3,4-dimethoxyphenyl are at a distance of -0.0058 (35) and 0.1132 (34) Å, respectively from the parent group B. In the second molecule, the 4-chloroanilinic group C (C16—C21/N2/CL2) and group D (C22—C28/O3/O4) of 3,4-dimethoxyphenyl are planar with r.m.s. deviation of 0.0094 and 0.0063 Å, respectively. The dihedral angle between C/D is 19.68 (7)°. The C-atoms C29 and C30 of 3,4-dimethoxyphenyl are at a distance of -0.2256 (33) and -0.2205 (31) Å, respectively from the parent group D. This shows that both molecules differ at large from each other. The molecules are stabilized through C—H···O type of H-bonding and π···π interactions (Table 1).

Experimental

Equimolar quantities of 4-chloroaniline and 3,4-dimethoxybenzaldehyde were refluxed in methanol for 30 min. The solution was kept at room temperature which afforded orange light yellow prisms of (I) after 48 h.

Refinement

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for other H-atoms.

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.

Crystal data

C15H14ClNO2F(000) = 1152
Mr = 275.72Dx = 1.322 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3456 reflections
a = 12.4227 (4) Åθ = 1.7–25.3°
b = 7.3638 (2) ŵ = 0.27 mm1
c = 30.4583 (13) ÅT = 296 K
β = 96.080 (2)°Prism, light yellow
V = 2770.60 (17) Å30.35 × 0.22 × 0.20 mm
Z = 8

Data collection

Bruker Kappa APEXII CCD diffractometer5007 independent reflections
Radiation source: fine-focus sealed tube3456 reflections with I > 2σ(I)
graphiteRint = 0.026
Detector resolution: 8.10 pixels mm-1θmax = 25.3°, θmin = 1.7°
ω scansh = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −8→8
Tmin = 0.932, Tmax = 0.950l = −36→29
20975 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0465P)2 + 1.0036P] where P = (Fo2 + 2Fc2)/3
5007 reflections(Δ/σ)max < 0.001
347 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.30 e Å3

Special details

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 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)

xyzUiso*/Ueq
Cl1−0.47381 (6)0.59742 (12)0.19551 (3)0.1029 (3)
O10.34541 (11)0.7300 (2)0.00839 (5)0.0666 (6)
O20.15540 (11)0.7756 (2)−0.03006 (4)0.0622 (5)
N1−0.10335 (14)0.6680 (2)0.09001 (5)0.0531 (6)
C1−0.18906 (15)0.6522 (3)0.11683 (6)0.0480 (6)
C2−0.27949 (16)0.5526 (3)0.10049 (7)0.0534 (7)
C3−0.36655 (17)0.5352 (3)0.12478 (7)0.0582 (8)
C4−0.36430 (18)0.6199 (3)0.16498 (8)0.0597 (8)
C5−0.27691 (19)0.7213 (3)0.18141 (7)0.0641 (8)
C6−0.18948 (17)0.7378 (3)0.15726 (7)0.0572 (8)
C7−0.00599 (17)0.6629 (3)0.10774 (7)0.0547 (7)
C80.08663 (16)0.6815 (3)0.08263 (7)0.0505 (7)
C90.07247 (15)0.7174 (3)0.03730 (6)0.0481 (7)
C100.15987 (16)0.7355 (3)0.01380 (6)0.0477 (6)
C110.26563 (16)0.7137 (3)0.03515 (7)0.0505 (7)
C120.27930 (17)0.6779 (3)0.07967 (7)0.0595 (8)
C130.19067 (17)0.6630 (3)0.10334 (7)0.0606 (8)
C140.45431 (17)0.7121 (4)0.02793 (9)0.0797 (10)
C150.05181 (18)0.8106 (4)−0.05280 (7)0.0704 (9)
Cl2−0.28854 (6)0.13333 (12)0.26687 (2)0.0916 (3)
O30.34354 (11)0.2151 (2)0.04035 (5)0.0685 (6)
O40.53216 (11)0.1383 (2)0.07674 (5)0.0614 (5)
N20.08863 (14)0.1523 (2)0.16357 (6)0.0538 (6)
C160.00252 (16)0.1438 (3)0.19048 (6)0.0474 (7)
C17−0.09141 (16)0.2363 (3)0.17535 (7)0.0526 (7)
C18−0.18002 (17)0.2347 (3)0.19879 (7)0.0575 (7)
C19−0.17623 (17)0.1391 (3)0.23760 (7)0.0535 (7)
C20−0.08492 (18)0.0463 (3)0.25324 (7)0.0614 (8)
C210.00371 (17)0.0481 (3)0.22977 (7)0.0572 (7)
C220.18473 (17)0.1189 (3)0.17922 (7)0.0597 (8)
C230.27594 (16)0.1226 (3)0.15321 (7)0.0547 (7)
C240.26207 (16)0.1687 (3)0.10854 (7)0.0511 (7)
C250.34811 (16)0.1725 (3)0.08394 (7)0.0502 (7)
C260.45269 (15)0.1286 (3)0.10403 (7)0.0515 (7)
C270.46640 (17)0.0814 (3)0.14774 (8)0.0654 (8)
C280.37878 (18)0.0795 (4)0.17212 (8)0.0700 (9)
C290.23950 (17)0.2317 (3)0.01634 (7)0.0672 (8)
C300.63635 (16)0.0663 (3)0.09192 (8)0.0675 (9)
H2−0.281360.497220.072970.0640*
H3−0.426380.466510.113970.0699*
H5−0.276410.778640.208630.0769*
H6−0.130160.807290.168280.0686*
H70.006530.646370.138130.0656*
H90.002910.729050.022960.0577*
H120.348700.663620.094000.0714*
H130.201120.640220.133530.0727*
H14A0.467540.797540.051690.1193*
H14B0.502940.735650.006110.1193*
H14C0.465810.591020.039140.1193*
H15A0.009310.70152−0.054030.1056*
H15B0.059860.85091−0.082250.1056*
H15C0.016160.90321−0.037500.1056*
H17−0.094470.300330.148930.0631*
H18−0.242290.298170.188400.0690*
H20−0.08271−0.017790.279630.0737*
H210.06554−0.015930.240410.0687*
H220.197760.090420.209060.0716*
H240.193280.197230.095260.0614*
H270.534810.050600.161040.0785*
H280.389220.048690.201870.0840*
H29A0.198690.122890.019820.1007*
H29B0.247290.24997−0.014370.1007*
H29C0.202240.333500.027360.1007*
H30A0.666410.133000.117410.1012*
H30B0.683300.076890.068960.1012*
H30C0.62931−0.059230.099600.1012*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0819 (5)0.1266 (7)0.1086 (6)0.0040 (4)0.0499 (4)0.0131 (5)
O10.0419 (8)0.0932 (12)0.0652 (10)−0.0014 (8)0.0074 (7)0.0011 (9)
O20.0502 (8)0.0884 (11)0.0482 (8)0.0024 (8)0.0058 (7)0.0031 (8)
N10.0510 (10)0.0576 (10)0.0509 (10)−0.0004 (8)0.0067 (8)0.0022 (8)
C10.0490 (11)0.0469 (11)0.0480 (11)0.0033 (9)0.0048 (9)0.0062 (9)
C20.0576 (13)0.0507 (12)0.0512 (12)0.0006 (10)0.0028 (10)0.0015 (10)
C30.0496 (12)0.0575 (13)0.0664 (14)−0.0020 (10)0.0005 (10)0.0109 (11)
C40.0568 (13)0.0607 (14)0.0640 (14)0.0086 (11)0.0179 (11)0.0117 (11)
C50.0749 (16)0.0635 (14)0.0554 (13)0.0048 (12)0.0139 (12)−0.0054 (11)
C60.0574 (13)0.0566 (13)0.0572 (13)−0.0035 (10)0.0045 (10)−0.0052 (10)
C70.0574 (13)0.0604 (13)0.0464 (11)0.0015 (10)0.0059 (10)0.0051 (10)
C80.0492 (12)0.0535 (12)0.0487 (11)0.0007 (9)0.0043 (9)0.0026 (9)
C90.0419 (11)0.0496 (12)0.0518 (12)0.0011 (9)0.0001 (9)−0.0002 (9)
C100.0482 (11)0.0469 (11)0.0472 (11)0.0005 (9)0.0015 (9)−0.0022 (9)
C110.0450 (11)0.0514 (12)0.0548 (12)−0.0009 (9)0.0043 (9)−0.0033 (10)
C120.0438 (11)0.0724 (15)0.0601 (14)0.0015 (10)−0.0049 (10)−0.0011 (11)
C130.0588 (13)0.0740 (15)0.0478 (12)0.0017 (11)0.0000 (10)0.0064 (11)
C140.0445 (13)0.113 (2)0.0814 (17)−0.0016 (13)0.0054 (12)−0.0137 (16)
C150.0656 (15)0.0966 (18)0.0477 (12)0.0126 (13)0.0000 (11)−0.0030 (12)
Cl20.0734 (4)0.1239 (6)0.0828 (5)0.0051 (4)0.0329 (3)−0.0075 (4)
O30.0441 (8)0.1016 (12)0.0596 (9)0.0077 (8)0.0045 (7)0.0180 (9)
O40.0406 (8)0.0748 (10)0.0686 (10)0.0043 (7)0.0045 (7)0.0094 (8)
N20.0529 (10)0.0587 (11)0.0503 (10)0.0024 (8)0.0072 (8)0.0034 (8)
C160.0516 (12)0.0447 (11)0.0452 (11)0.0001 (9)0.0023 (9)−0.0007 (9)
C170.0593 (13)0.0538 (12)0.0432 (11)0.0071 (10)−0.0019 (9)0.0047 (9)
C180.0528 (12)0.0617 (13)0.0562 (13)0.0120 (10)−0.0030 (10)−0.0051 (11)
C190.0538 (12)0.0565 (12)0.0509 (12)0.0000 (10)0.0094 (10)−0.0085 (10)
C200.0689 (15)0.0616 (14)0.0543 (13)0.0024 (11)0.0092 (11)0.0119 (11)
C210.0549 (12)0.0573 (13)0.0586 (13)0.0091 (10)0.0021 (10)0.0126 (11)
C220.0588 (14)0.0723 (15)0.0474 (12)0.0005 (11)0.0035 (10)0.0030 (11)
C230.0500 (12)0.0606 (13)0.0531 (12)0.0010 (10)0.0031 (10)0.0013 (10)
C240.0425 (11)0.0537 (12)0.0564 (12)0.0045 (9)0.0016 (9)0.0031 (10)
C250.0471 (11)0.0496 (12)0.0531 (12)0.0015 (9)0.0011 (9)0.0050 (10)
C260.0423 (11)0.0512 (12)0.0600 (13)0.0006 (9)0.0005 (9)0.0018 (10)
C270.0440 (12)0.0853 (17)0.0642 (14)0.0044 (11)−0.0073 (10)0.0105 (12)
C280.0580 (14)0.0963 (18)0.0538 (13)0.0041 (12)−0.0028 (11)0.0113 (13)
C290.0576 (13)0.0810 (16)0.0606 (14)0.0047 (12)−0.0046 (11)0.0085 (12)
C300.0416 (12)0.0733 (15)0.0867 (17)0.0067 (10)0.0029 (11)0.0070 (13)

Geometric parameters (Å, °)

Cl1—C41.735 (2)C13—H130.9300
Cl2—C191.734 (2)C14—H14A0.9600
O1—C111.354 (2)C14—H14B0.9600
O1—C141.425 (3)C14—H14C0.9600
O2—C151.419 (3)C15—H15A0.9600
O2—C101.364 (2)C15—H15B0.9600
O3—C251.360 (3)C15—H15C0.9600
O3—C291.421 (3)C16—C171.387 (3)
O4—C301.430 (3)C16—C211.388 (3)
O4—C261.358 (2)C17—C181.374 (3)
N1—C71.272 (3)C18—C191.372 (3)
N1—C11.414 (2)C19—C201.366 (3)
N2—C221.262 (3)C20—C211.375 (3)
N2—C161.416 (3)C22—C231.450 (3)
C1—C61.384 (3)C23—C241.395 (3)
C1—C21.389 (3)C23—C281.382 (3)
C2—C31.380 (3)C24—C251.369 (3)
C3—C41.372 (3)C25—C261.414 (3)
C4—C51.368 (3)C26—C271.369 (3)
C5—C61.380 (3)C27—C281.381 (3)
C7—C81.454 (3)C17—H170.9300
C8—C91.398 (3)C18—H180.9300
C8—C131.384 (3)C20—H200.9300
C9—C101.369 (3)C21—H210.9300
C10—C111.412 (3)C22—H220.9300
C11—C121.374 (3)C24—H240.9300
C12—C131.383 (3)C27—H270.9300
C2—H20.9300C28—H280.9300
C3—H30.9300C29—H29A0.9600
C5—H50.9300C29—H29B0.9600
C6—H60.9300C29—H29C0.9600
C7—H70.9300C30—H30A0.9600
C9—H90.9300C30—H30B0.9600
C12—H120.9300C30—H30C0.9600
C11—O1—C14117.62 (17)H15A—C15—H15B109.00
C10—O2—C15117.28 (15)O2—C15—H15A109.00
C25—O3—C29117.64 (16)O2—C15—H15B109.00
C26—O4—C30118.33 (17)N2—C16—C17116.51 (17)
C1—N1—C7119.52 (17)N2—C16—C21125.58 (19)
C16—N2—C22121.01 (18)C17—C16—C21117.89 (19)
N1—C1—C6123.42 (18)C16—C17—C18121.0 (2)
N1—C1—C2117.81 (17)C17—C18—C19119.7 (2)
C2—C1—C6118.70 (18)Cl2—C19—C18119.96 (17)
C1—C2—C3120.48 (19)Cl2—C19—C20119.48 (17)
C2—C3—C4119.6 (2)C18—C19—C20120.6 (2)
C3—C4—C5121.0 (2)C19—C20—C21119.7 (2)
Cl1—C4—C3119.47 (17)C16—C21—C20121.2 (2)
Cl1—C4—C5119.53 (18)N2—C22—C23123.6 (2)
C4—C5—C6119.5 (2)C22—C23—C24120.96 (18)
C1—C6—C5120.8 (2)C22—C23—C28120.6 (2)
N1—C7—C8122.94 (19)C24—C23—C28118.41 (19)
C7—C8—C9120.89 (18)C23—C24—C25121.05 (19)
C7—C8—C13120.26 (19)O3—C25—C24125.80 (19)
C9—C8—C13118.85 (19)O3—C25—C26114.64 (17)
C8—C9—C10120.72 (18)C24—C25—C26119.57 (19)
O2—C10—C11114.53 (17)O4—C26—C25114.67 (18)
O2—C10—C9125.53 (18)O4—C26—C27125.80 (18)
C9—C10—C11119.93 (17)C25—C26—C27119.54 (19)
O1—C11—C10114.68 (18)C26—C27—C28120.1 (2)
O1—C11—C12126.11 (19)C23—C28—C27121.3 (2)
C10—C11—C12119.21 (19)C16—C17—H17119.00
C11—C12—C13120.5 (2)C18—C17—H17119.00
C8—C13—C12120.8 (2)C17—C18—H18120.00
C1—C2—H2120.00C19—C18—H18120.00
C3—C2—H2120.00C19—C20—H20120.00
C2—C3—H3120.00C21—C20—H20120.00
C4—C3—H3120.00C16—C21—H21119.00
C4—C5—H5120.00C20—C21—H21119.00
C6—C5—H5120.00N2—C22—H22118.00
C1—C6—H6120.00C23—C22—H22118.00
C5—C6—H6120.00C23—C24—H24119.00
C8—C7—H7119.00C25—C24—H24119.00
N1—C7—H7119.00C26—C27—H27120.00
C8—C9—H9120.00C28—C27—H27120.00
C10—C9—H9120.00C23—C28—H28119.00
C11—C12—H12120.00C27—C28—H28119.00
C13—C12—H12120.00O3—C29—H29A109.00
C12—C13—H13120.00O3—C29—H29B109.00
C8—C13—H13120.00O3—C29—H29C109.00
O1—C14—H14B109.00H29A—C29—H29B109.00
H14A—C14—H14C109.00H29A—C29—H29C109.00
O1—C14—H14C109.00H29B—C29—H29C109.00
H14A—C14—H14B109.00O4—C30—H30A109.00
O1—C14—H14A109.00O4—C30—H30B109.00
H14B—C14—H14C109.00O4—C30—H30C109.00
O2—C15—H15C109.00H30A—C30—H30B109.00
H15A—C15—H15C109.00H30A—C30—H30C109.00
H15B—C15—H15C109.00H30B—C30—H30C110.00
C14—O1—C11—C10179.1 (2)O2—C10—C11—O1−2.1 (3)
C14—O1—C11—C12−1.3 (3)O2—C10—C11—C12178.25 (19)
C15—O2—C10—C93.4 (3)C9—C10—C11—O1178.4 (2)
C15—O2—C10—C11−176.1 (2)C9—C10—C11—C12−1.3 (3)
C29—O3—C25—C26169.99 (18)O1—C11—C12—C13−179.5 (2)
C29—O3—C25—C24−9.7 (3)C10—C11—C12—C130.1 (3)
C30—O4—C26—C25−169.27 (18)C11—C12—C13—C80.8 (3)
C30—O4—C26—C2710.8 (3)N2—C16—C17—C18179.24 (19)
C1—N1—C7—C8−178.84 (19)C21—C16—C17—C180.7 (3)
C7—N1—C1—C641.7 (3)N2—C16—C21—C20−179.1 (2)
C7—N1—C1—C2−141.6 (2)C17—C16—C21—C20−0.6 (3)
C22—N2—C16—C21−21.7 (3)C16—C17—C18—C19−0.5 (3)
C16—N2—C22—C23179.0 (2)C17—C18—C19—Cl2−178.91 (17)
C22—N2—C16—C17159.9 (2)C17—C18—C19—C200.3 (3)
N1—C1—C6—C5178.2 (2)Cl2—C19—C20—C21178.95 (17)
C6—C1—C2—C3−1.9 (3)C18—C19—C20—C21−0.3 (3)
N1—C1—C2—C3−178.78 (19)C19—C20—C21—C160.5 (3)
C2—C1—C6—C51.5 (3)N2—C22—C23—C241.6 (3)
C1—C2—C3—C41.2 (3)N2—C22—C23—C28−178.1 (2)
C2—C3—C4—Cl1−179.88 (17)C22—C23—C24—C25179.9 (2)
C2—C3—C4—C5−0.1 (3)C28—C23—C24—C25−0.4 (3)
Cl1—C4—C5—C6179.46 (17)C22—C23—C28—C27179.6 (2)
C3—C4—C5—C6−0.3 (3)C24—C23—C28—C270.0 (4)
C4—C5—C6—C1−0.4 (3)C23—C24—C25—O3179.9 (2)
N1—C7—C8—C93.9 (3)C23—C24—C25—C260.2 (3)
N1—C7—C8—C13−175.8 (2)O3—C25—C26—O40.8 (3)
C7—C8—C9—C10179.8 (2)O3—C25—C26—C27−179.21 (19)
C9—C8—C13—C12−0.6 (3)C24—C25—C26—O4−179.42 (19)
C13—C8—C9—C10−0.5 (3)C24—C25—C26—C270.5 (3)
C7—C8—C13—C12179.1 (2)O4—C26—C27—C28179.0 (2)
C8—C9—C10—C111.5 (3)C25—C26—C27—C28−1.0 (3)
C8—C9—C10—O2−178.0 (2)C26—C27—C28—C230.7 (4)

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C8–C13 and C16–C21 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C14—H14B···O3i0.962.523.468 (3)170
C6—H6···Cg3ii0.932.853.602 (2)139
C18—H18···Cg10.932.893.588 (2)133
C21—H21···Cg3iii0.932.883.549 (2)130
C29—H29C···Cg20.962.883.782 (2)157
C30—H30C···Cg1iv0.962.763.613 (2)148

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5610).

References

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