PMCID: PMC2961540(Z)-2-(2-Chloro-3,3,3-trifluoro&#x000prop-1-en&#x000yl)-6-methoxy&#x000phenyl acetate,a ,a and
a,*Correspondence e-mail:
The crystal structure of the title compound, C12H10ClF3O3, was determined in order to establish the configuration of the C=double bond. The compound was found to be the Z isomer. The crystal structure is dominated by ClO halogen bonds [ClO = 3.111 (3) Å], as well as C—HO and C—HF hydrogen-bonding inter&#x000actions, that connect neighboring mol&#x000ecules into a three-dimensional supra&#x000molecular network.For related literature, see: Dmowski (1985); Fujita & Hiyama (1986); Nenajdenko et al.(2005); Politzer et al. (2007).
Crystal data
C12H10ClF3O3
r = 294.65Triclinic,
a = 8.6168 (19) Å
b = 8.6850 (19) Å
c = 9.723 (2) Åα = 77.323 (3)°β = 70.869 (3)°γ = 84.010 (3)°
V = 670.3 (3) Å3
Z = 2Mo Kα radiation&#x003 = 0.32 mm−1
T = 293 (2) K0.16 × 0.10 × 0.09 mm
Data collection
Bruker APEX CCD area-detector diffractometerAbsorption correction: multi-scan (SADABS; Sheldrick, 1996) T
min = 0.943, T
max = 0.9683677 measured reflections2551 independent reflections1967 reflections with I > 2σ(I)
int = 0.009
Refinement
2 > 2σ(F
2)] = 0.052
2) = 0.146
S = 1.032551 reflections174 parametersH-atom parameters constrainedΔρmax = 0.31 e Å−3
Δρmin = &#x e Å−3
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.Hydrogen-bond geometry (Å, °)Crystal structure: contains datablocks global, I. DOI:
(16K, cif)Structure factors: contains datablocks I. DOI:
(125K, hkl)Additional supplementary materials: ; ;
This work was supported by Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, People’s Republic of China.
Experimental
The title compound was synthesized by a modified literature procedure
(Fujita & Hiyama, 1986). Zinc
powder (3.25 g, 50 mmol) and acetic anhydride (3.06 g, 30 mmol) were added
into a solution of 2-hydroxy-3-methoxybenzaldehyde (1.52 g,10 mmol) in DMF (20 ml, dried by 4Å molecular sieve) under an argon atmosphere at room
temperature.
Then 1,1,1-trichloro-2,2,2-trifluoroethane (5.63 g, 30 mmol)
was added dropwise
to the mixture over ten minutes with fierce stirring.
The reaction was monitored by
thin layer chromatography. After completion, the reaction mixture was treated
with saturated aqueous ammonium chloride solution (150 ml), and extracted with
diethyl ether (3 × 50 ml). The organic phase was dried with magnesium
sulfate, concentrated, and purification by silica gel column chromatography
using petroleum ether as the eluent (Rf = 0.15). The
purified product was recrystallized from petroleum ether to obtain colorless
platelike crystals (1.47 g, 50%).
Refinement
H atoms were placed geometrically and refined with fixed individual displacement
parameters [Uiso(H) = 1.2Ueq(C,N)] (1.5 for methyl H
atoms), using a riding model with C—H distances of 0.93 Å for Csp2
and 0.96 Å for methyl H atoms.Figures The structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.Perspective view of the packing structure of the title compound along the c axis. For the sake of clarity, H atoms not involved in the motifs shown have been omitted. Symmetry equivalent atoms marked i are created by the operator x, y+ 1, z).Crystal data C12H10ClF3O3Z = 2Mr = 294.65F000 = 300Triclinic, P1Dx = 1.460 Mg m−3Hall symbol:
-P 1Mo Kα radiation &#x003 = 0.71073 Åa = 8.6168 (19) ÅCell parameters from 1359 reflectionsb = 8.6850 (19) Åθ = 2.3&#x&#x000c = 9.723 (2) ŵ = 0.32 mm−1α = 77.323 (3)&#x000T = 293 (2) Kβ = 70.869 (3)&#x000Sheet, colorlessγ = 84.010 (3)&#x0000.16 × 0.10 × 0.09 mmV = 670.3 (3)
Å3Data collection Bruker APEX CCD area-detector
diffractometer2551 independent reflectionsRadiation source: fine-focus sealed tube1967 reflections with I > 2σ(I)Monochromator: graphiteRint = 0.009T = 293(2) Kθmax = 26.0&#x000 and ω scansθmin = 2.3&#x000Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −10→10Tmin = 0.943, Tmax = 0.968k = −10→43677 measured reflectionsl = −11→11Refinement Refinement on F2Secondary atom site location: difference Fourier mapLeast-squares matrix: fullHydrogen site location: inferred from neighbouring sitesR[F2 > 2σ(F2)] = 0.052H-atom parameters constrainedwR(F2) = 0.146 
w = 1/[σ2(Fo2) + (0.0746P)2 + 0.2352P] where P = (Fo2 + 2Fc2)/3S = 1.03(Δ/σ)max = 0.0262551 reflectionsΔρmax = 0.31 e Å−3174 parametersΔρmin = &#x e Å−3Primary atom site location: structure-invariant direct methodsExtinction correction: noneSpecial details 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
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) xyzUiso*/UeqCl0.29665 (10)0.96976 (8)0.19741 (8)0.0749 (3)F10.3028 (3)0.8620 (2)0.5096 (2)0.0953 (6)F20.5445 (3)0.9077 (3)0.3604 (3)0.1170 (8)F30.4779 (3)0.6737 (3)0.4667 (2)0.1112 (8)O10.24346 (19)0.36598 (19)0.26609 (17)0.0504 (4)O2&#x3 (2)0.4383 (3)0.3538 (2)0.0725 (6)O30.1566 (2)0.2860 (2)0.0539 (2)0.0692 (5)C10.4235 (4)0.8063 (4)0.4042 (4)0.0719 (8)C20.3680 (3)0.7914 (3)0.2776 (3)0.0538 (6)C30.3712 (3)0.6540 (3)0.2383 (3)0.0508 (6)H30.40710.56720.29660.061*C40.3255 (3)0.6202 (3)0.1150 (3)0.0481 (5)C50.3518 (3)0.7237 (3)&#x9 (3)0.0602 (7)H50.39720.8211&#x80.072*C60.3106 (4)0.6812 (4)&#x6 (3)0.0674 (7)H60.32870.7509&#x40.081*C70.2429 (3)0.5379 (4)&#x9 (3)0.0630 (7)H70.21370.5126&#x00.076*C80.2185 (3)0.4316 (3)0.0209 (3)0.0539 (6)C90.2602 (3)0.4751 (3)0.1335 (2)0.0467 (5)C100.0917 (3)0.3562 (3)0.3710 (3)0.0519 (6)C110.0957 (4)0.2335 (4)0.5034 (3)0.0744 (8)H11A0.01050.25710.58930.112*H11B0.20060.23230.51840.112*H11C0.07880.13200.48780.112*C120.1195 (4)0.2342 (4)&#x0 (4)0.0830 (9)H12A0.04360.3086&#x90.124*H12B0.07130.1326&#x80.124*H12C0.21880.2266&#x60.124*Atomic displacement parameters (Å2) U11U22U33U12U13U23Cl0.1011 (6)0.0514 (4)0.0688 (5)0.0024 (4)&#x6 (4)&#x3 (3)F10.1230 (16)0.1053 (15)0.0688 (11)0.0132 (12)&#x2 (11)&#x9 (11)F20.1136 (16)0.1319 (19)0.1389 (19)&#x6 (14)&#x5 (14)&#x5 (16)F30.173 (2)0.0917 (14)0.1183 (16)0.0367 (14)&#x0 (16)&#x4 (12)O10.0533 (9)0.0474 (9)0.0512 (9)0.0015 (7)&#x5 (8)&#x4 (7)O20.0595 (11)0.0929 (15)0.0630 (12)0.0129 (10)&#x6 (9)&#x1 (10)O30.0895 (14)0.0579 (11)0.0799 (13)&#x1 (10)&#x0 (11)&#x3 (10)C10.085 (2)0.0677 (18)0.080 (2)0.0004 (16)&#x9 (17)&#x1 (16)C20.0559 (14)0.0541 (14)0.0538 (14)&#x4 (11)&#x5 (11)&#x6 (11)C30.0541 (13)0.0516 (13)0.0490 (13)&#x3 (11)&#x4 (11)&#x1 (11)C40.0474 (12)0.0524 (13)0.0452 (13)&#x1 (10)&#x1 (10)&#x0 (10)C50.0684 (16)0.0609 (16)0.0483 (14)&#x5 (13)&#x2 (12)&#x0 (12)C60.0817 (19)0.0748 (19)0.0430 (14)&#x6 (15)&#x1 (13)&#x4 (13)C70.0689 (17)0.0790 (19)0.0505 (15)0.0093 (14)&#x0 (13)&#x9 (13)C80.0564 (14)0.0557 (15)0.0586 (15)0.0065 (11)&#x9 (12)&#x7 (12)C90.0474 (12)0.0484 (13)0.0452 (12)0.0042 (10)&#x7 (10)&#x2 (10)C100.0590 (15)0.0514 (13)0.0510 (14)&#x0 (12)&#x4 (11)&#x1 (11)C110.0800 (19)0.0706 (19)0.0617 (17)&#x9 (15)&#x9 (15)&#x5 (14)C120.091 (2)0.084 (2)0.098 (2)0.0006 (18)&#x7 (19)&#x9 (19)Geometric parameters (Å, °) Cl—C21.724 (3)C5—C61.368 (4)F1—C11.334 (4)C5—H50.9300F2—C11.335 (4)C6—C71.378 (4)F3—C11.297 (4)C6—H60.9300O1—C101.367 (3)C7—C81.386 (4)O1—C91.397 (3)C7—H70.9300O2—C101.188 (3)C8—C91.392 (3)O3—C81.356 (3)C10—C111.488 (4)O3—C121.427 (3)C11—H11A0.9600C1—C21.493 (4)C11—H11B0.9600C2—C31.325 (3)C11—H11C0.9600C3—C41.472 (3)C12—H12A0.9600C3—H30.9300C12—H12B0.9600C4—C91.385 (3)C12—H12C0.9600C4—C51.397 (3)C10—O1—C9117.36 (18)C6—C7—H7120.1C8—O3—C12117.3 (2)C8—C7—H7120.1F3—C1—F1107.4 (3)O3—C8—C7125.8 (2)F3—C1—F2106.7 (3)O3—C8—C9115.7 (2)F1—C1—F2106.0 (2)C7—C8—C9118.5 (2)F3—C1—C2113.2 (2)C4—C9—C8121.9 (2)F1—C1—C2111.7 (3)C4—C9—O1119.1 (2)F2—C1—C2111.4 (3)C8—C9—O1118.9 (2)C3—C2—C1122.2 (2)O2—C10—O1122.5 (2)C3—C2—Cl126.0 (2)O2—C10—C11127.4 (3)C1—C2—Cl111.8 (2)O1—C10—C11110.1 (2)C2—C3—C4128.8 (2)C10—C11—H11A109.5C2—C3—H3115.6C10—C11—H11B109.5C4—C3—H3115.6H11A—C11—H11B109.5C9—C4—C5118.3 (2)C10—C11—H11C109.5C9—C4—C3118.2 (2)H11A—C11—H11C109.5C5—C4—C3123.4 (2)H11B—C11—H11C109.5C6—C5—C4119.8 (3)O3—C12—H12A109.5C6—C5—H5120.1O3—C12—H12B109.5C4—C5—H5120.1H12A—C12—H12B109.5C5—C6—C7121.7 (3)O3—C12—H12C109.5C5—C6—H6119.2H12A—C12—H12C109.5C7—C6—H6119.2H12B—C12—H12C109.5C6—C7—C8119.7 (2)Hydrogen-bond geometry (Å, °) D—H···AD—HH···AD···AD—H···AC6—H6···F1i0.932.643.508 (3)156C7—H7···O2ii0.932.603.430 (3)149Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z.Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ).Bruker (1998). SMART Bruker AXS Inc., Madison, Wisconsin, USA.Bruker (2003). SAINT-Plus Bruker AXS, Inc., Madison, Wisconsin, USA.Dmowski, W. (1985). J. Fluorine Chem.29, 273&#x.Fujita, M. & Hiyama, T. (1986). Tetrahedron Lett.27, 3655&#x.Nenajdenko, V. G., Varseev, G. N., Shastin, A. V. & Balenkova, E. S. (2005). J. Fluorine Chem.126, 907&#x.Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model.13, 305&#x.
[]Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.Sheldrick, G. M. (2008). Acta Cryst. A64, 112&#x.
[]Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography&PMCID: PMC29615802-(2-Hydroxy&#x000benzyl&#x000ideneamino)benzonitrile,a ,a,* and
aCorrespondence e-mail:
This article has been
other articles in PMC.The mol&#x000ecule of the title compound, C14H10N2O, displays a trans configuration with respect to the C=N double bond. The mol&#x000ecu the two aromatic rings make a dihedral angle of 9.3 (3)°. Such a planar conformation is induced by the strong intra&#x000molecular O—HN hydrogen bond between the imine and hydroxyl groups.For the structures of similar Schiff base compounds, see: Cheng et al. (). For related literature, see: Chen et al. (2008); Elmah et al. (1999); May et al. (2004); Weber et al. (2007); Xu et al. (2008). For bond-length data, see: Allen et al. (1987).
Crystal data
r = 222.24Monoclinic,
a = 4.7667 (10) Å
b = 16.190 (3) Å
c = 7.6714 (15) Åβ = 93.30 (3)°
V = 591.0 (2) Å3
Z = 2Mo Kα radiation&#x003 = 0.08 mm−1
T = 293 (2) K0.20 × 0.05 × 0.05 mm
Data collection
Rigaku Mercury2 diffractometerAbsorption correction: multi-scan (CrystalClear; Rigaku, 2005) T
min = 0.981, T
max = 1.00 (expected range = 0.977&#x)5470 measured reflections1201 independent reflections633 reflections with I > 2σ(I)
int = 0.105
Refinement
2 > 2σ(F
2)] = 0.061
2) = 0.136
S = 1.031201 reflections155 parameters1 restraintH-atom parameters constrainedΔρmax = 0.14 e Å−3
Δρmin = &#x e Å−3
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.Hydrogen-bond geometry (Å, °)Crystal structure: contains datablocks I, global. DOI:
(15K, cif)Structure factors: contains datablocks I. DOI:
(59K, hkl)Additional supplementary materials: ; ;
HJX acknowledges a Start-up Grant from Southeast University.
Experimental
All chemicals were obtained from commercial sources and used without further
purification except for salicylaldehyde which is distiled under reduced
pressure before use. 3-aminobenzonitrile (1.18 g, 10 mmol) and salicylaldehyde
(1.22 g, 10 mmol) were dissolved in ethanol (20 ml). The mixture was heated to
reflux for 4 h, then cooled to room temperature overnight and large amounts of
a yellow precipitate were formed. Yellow crystal was obtained by
recrystallization from ethyl alcohol(yield: 85%). 1H-NMR(CDCl3, 300 MHz):
δ6.98 (t, 1 H), 7.08 (d, 1 H), 7.37(t, 2 H), 7.45 (t, 2 H), 7.69 (m, 2H),
8.72 (s, 1 H). Esi-MS: calcd for C14H9N2O – H m/z 221.24,
found 221.34. For the X-ray diffraction analysis, suitable single crystals of
compound (I) were obtained after one week by slow evaporation from an ethyl
alcohol solution.
Refinement
All H atoms attached to C atoms and O atom were fixed geometrically and treated
as riding with C—H = 0.93 Å and O—H = 0.82Å with Uiso(H) =
1.2Ueq(C) or Uiso(H) = 1.5Ueq(O).In the absence of significant anomalous scattering, the absolute structure
could not be reliably determined and then the Friedel pairs were merged and
any references to the Flack parameter were removed.Figures A view of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as smal spheres of arbitrary radii. Intramolecular H bond is shown as dashed line.Crystal data C14H10N2OF000 = 232Mr = 222.24Dx = 1.249 Mg m−3Monoclinic, P21Mo Kα radiation &#x003 = 0.71073 ÅHall symbol:
P 2ybCell parameters from 4123 reflectionsa = 4.7667 (10) Åθ = 3.7&#x&#x000b = 16.190 (3) ŵ = 0.08 mm−1c = 7.6714 (15) ÅT = 293 (2) Kβ = 93.30 (3)&#x000Block, colorlessV = 591.0 (2)
Å30.20 × 0.05 × 0.05 mmZ = 2Data collection Rigaku Mercury2
diffractometer1201 independent reflectionsRadiation source: fine-focus sealed tube633 reflections with I > 2σ(I)Monochromator: graphiteRint = 0.105Detector resolution: 13.6612 pixels mm-1θmax = 26.0&#x000T = 293(2) Kθmin = 3.7&#x000ω scansh = −5→5Absorption correction: multi-scan(CrystalC Rigaku, 2005)k = −19→19Tmin = 0.981, Tmax = 1.00l = −9→95470 measured reflectionsRefinement Refinement on F2Secondary atom site location: difference Fourier mapLeast-squares matrix: fullHydrogen site location: inferred from neighbouring sitesR[F2 > 2σ(F2)] = 0.061H-atom parameters constrainedwR(F2) = 0.136 
w = 1/[σ2(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3S = 1.03(Δ/σ)max < 0.0011201 reflectionsΔρmax = 0.15 e Å−3155 parametersΔρmin = &#x e Å−31 restraintExtinction correction: nonePrimary atom site location: structure-invariant direct methodsSpecial details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.
The cell esds are taken
into account individually in the estimation of esds in distances, angles
correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.
An approximate (isotropic)
treatment of cell esds is used for estimating esds 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) xyzUiso*/UeqC1&#x0 (10)0.5064 (3)0.8304 (7)0.0474 (15)C2&#x2 (11)0.5462 (4)0.6745 (9)0.0580 (16)C3&#x9 (13)0.6076 (4)0.6777 (10)0.076 (2)H3&#x40.63430.57470.091*C4&#x8 (14)0.6293 (4)0.8306 (12)0.0747 (19)H4&#x30.67120.83030.090*C5&#x0 (12)0.5906 (4)0.9860 (10)0.073 (2)H5&#x00.60471.08870.087*C6&#x6 (11)0.5303 (4)0.9858 (8)0.0639 (16)H6&#x20.50521.09040.077*C70.2044 (10)0.4416 (3)0.8361 (7)0.0480 (14)H70.25920.41790.94310.058*C80.5180 (10)0.3518 (3)0.7054 (6)0.0431 (14)C90.6040 (10)0.3216 (3)0.5473 (7)0.0526 (15)C100.7977 (11)0.2575 (4)0.5400 (8)0.0657 (17)H100.84840.23750.43260.079*C110.9127 (13)0.2241 (4)0.6912 (9)0.0685 (18)H111.04170.18120.68770.082*C120.8365 (11)0.2546 (4)0.8477 (9)0.0623 (17)H120.91820.23240.95030.075*C130.6393 (11)0.3180 (3)0.8582 (7)0.0565 (15)H130.58990.33730.96640.068*C140.4758 (15)0.3547 (5)0.3888 (9)0.093 (2)N10.3182 (9)0.4157 (2)0.6972 (5)0.0459 (11)N20.3736 (15)0.3796 (5)0.2608 (8)0.147 (3)O10.0028 (9)0.5256 (3)0.5203 (5)0.0815 (14)H10.11740.48810.53480.122*Atomic displacement parameters (Å2) U11U22U33U12U13U23C10.040 (3)0.047 (4)0.055 (4)&#x (3)0.005 (3)&#x (3)C20.052 (3)0.044 (4)0.079 (5)0.005 (3)0.013 (3)0.011 (3)C30.067 (5)0.068 (5)0.094 (6)0.010 (4)0.014 (4)0.020 (4)C40.063 (4)0.043 (4)0.119 (6)0.012 (4)0.013 (4)&#x (4)C50.051 (4)0.079 (5)0.089 (5)0.002 (3)0.014 (4)&#x (4)C60.054 (4)0.075 (5)0.062 (4)&#x (4)&#x (3)&#x (3)C70.043 (3)0.053 (4)0.047 (4)0.002 (3)&#x (2)&#x (3)C80.046 (3)0.042 (4)0.042 (3)&#x (3)0.004 (2)&#x (2)C90.050 (3)0.060 (4)0.048 (4)0.004 (3)0.001 (3)0.003 (3)C100.065 (4)0.068 (5)0.065 (4)0.009 (3)0.005 (3)&#x (3)C110.060 (4)0.072 (5)0.073 (5)0.007 (4)0.004 (3)&#x (4)C120.056 (4)0.052 (4)0.080 (5)0.010 (3)0.006 (3)0.017 (3)C130.059 (4)0.061 (4)0.050 (4)0.006 (3)0.010 (3)0.007 (3)C140.093 (5)0.135 (7)0.052 (4)0.042 (5)0.005 (4)&#x (4)N10.049 (3)0.041 (3)0.048 (3)&#x (2)0.0079 (19)0.000 (2)N20.162 (7)0.225 (9)0.053 (4)0.106 (6)&#x (4)0.010 (5)O10.085 (3)0.092 (4)0.069 (3)0.028 (2)0.020 (2)0.030 (2)Geometric parameters (Å, °) C1—C61.405 (7)C8—C131.389 (7)C1—C21.406 (7)C8—C91.391 (6)C1—C71.450 (6)C8—N11.406 (6)C2—O11.345 (7)C9—C101.393 (7)C2—C31.385 (8)C9—C141.433 (9)C3—C41.363 (9)C10—C111.365 (8)C3—H30.9300C10—H100.9300C4—C51.381 (9)C11—C121.366 (8)C4—H40.9300C11—H110.9300C5—C61.387 (8)C12—C131.397 (7)C5—H50.9300C12—H120.9300C6—H60.9300C13—H130.9300C7—N11.293 (5)C14—N21.144 (7)C7—H70.9300O1—H10.8200C6—C1—C2118.3 (5)C13—C8—C9117.9 (5)C6—C1—C7119.1 (5)C13—C8—N1125.2 (5)C2—C1—C7122.6 (5)C9—C8—N1116.9 (4)O1—C2—C3118.5 (6)C8—C9—C10121.8 (5)O1—C2—C1121.7 (5)C8—C9—C14118.4 (5)C3—C2—C1119.8 (6)C10—C9—C14119.7 (5)C4—C3—C2120.5 (6)C11—C10—C9119.7 (6)C4—C3—H3119.8C11—C10—H10120.2C2—C3—H3119.8C9—C10—H10120.2C3—C4—C5121.6 (6)C10—C11—C12119.3 (6)C3—C4—H4119.2C10—C11—H11120.3C5—C4—H4119.2C12—C11—H11120.3C4—C5—C6118.6 (6)C11—C12—C13122.0 (6)C4—C5—H5120.7C11—C12—H12119.0C6—C5—H5120.7C13—C12—H12119.0C5—C6—C1121.2 (6)C8—C13—C12119.3 (5)C5—C6—H6119.4C8—C13—H13120.3C1—C6—H6119.4C12—C13—H13120.3N1—C7—C1122.1 (4)N2—C14—C9178.6 (8)N1—C7—H7118.9C7—N1—C8121.1 (4)C1—C7—H7118.9C2—O1—H1109.5Hydrogen-bond geometry (Å, °) D—H···AD—HH···AD···AD—H···AO1—H1···N10.821.922.651 (6)147Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ).Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc.130, 2170&#x.
[]Cheng, K., You, Z.-L., Li, Y.-G. & Zhu, H.-L. (2005). Acta Cryst. E61, o1137&#x0.Cheng, K., Zhu, H.-L., Li, Z.-B. & Yan, Z. (2006). Acta Cryst. E62, o2417&#x0.Elmah, A., Kabak, M. & Elerman, Y. (1999). J. Mol. Struct.484, 229&#x.Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.May, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc.126, 4145&#x.
[]Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.Sheldrick, G. M. (2008). Acta Cryst. A64, 112&#x.
[]Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem.633, 1159&#x.Xu, H.-J., Gong, X.-X. & Wang, H. (2008). Acta Cryst. E64, o638. []
[]Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography
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