PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o934.
Published online 2009 March 31. doi:  10.1107/S1600536809011416
PMCID: PMC2968797

2-[(4-Bromo­phen­yl)imino­meth­yl]-3,5-dimethoxy­phenol

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C15H14BrNO3, with very similar geometrical parameters. Each mol­ecule adopts the phenol–imine tautomeric form, with strong intra­molecular O—H(...)N hydrogen bonds. The two mol­ecules are non-planar, the dihedral angles between the two aromatic rings being are 24.6 (2) and 30.30 (13)°.

Related literature

For bond-length data, see: Petek et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o934-scheme1.jpg

Experimental

Crystal data

  • C15H14BrNO3
  • M r = 336.18
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o934-efi1.jpg
  • a = 8.2655 (5) Å
  • b = 9.7305 (6) Å
  • c = 18.3806 (11) Å
  • α = 97.177 (5)°
  • β = 92.796 (5)°
  • γ = 106.214 (5)°
  • V = 1402.94 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.94 mm−1
  • T = 296 K
  • 0.67 × 0.38 × 0.09 mm

Data collection

  • Stoe IPDS-2 diffractometer
  • Absorption correction: integration (X-RED; Stoe & Cie, 2002 [triangle]) T min = 0.421, T max = 0.839
  • 20096 measured reflections
  • 5514 independent reflections
  • 3901 reflections with I > 2σ(I)
  • R int = 0.080

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.112
  • S = 1.02
  • 5514 reflections
  • 369 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.61 e Å−3
  • Δρmin = −0.92 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); 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]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011416/bt2917sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011416/bt2917Isup2.hkl

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSI-2 diffractometer (purchased under grant No. F279 of the University Research Fund).

supplementary crystallographic information

Comment

The extensive application of Schiff bases in industry and in analytical determinations has attracted attention for decades. The overall behaviour of these compounds has been ascribed to a proton-transfer reaction between a phenol-imine and a keto-amine tautomer. It is claimed that phenol-imine tautomerism is dominant in salicylaldimine, while the keto-amine form is preferred in naphthaldimine Schiff bases, depending on the solvent polarities. Our X-ray investigation of the title compound has indicated that the phenol-imine tautomer is favoured over the keto-amine tautomer.

An ORTEP view of the molecule is shown in Fig. 1. There are two independent molecules in the asymmetric unit which have very similar geometrical parameters. Both molecules adopt the phenol-imine tautomeric form and have a strong intramolecular O—H···N hydrogen bond whose details are given in Table 1. The C7—N1 [1.296 (4) Å] and C22—N2 [1.296 (4) Å] bond distances are of double-bond character, whereas, the C2—O1 [1.344 (4) Å] and C17—O4 [1.342 (4) Å] distances are single bonds. These distances are similar to other values reported in the literature [1.2889 (15) and 1.2891 (14) Å for C=N and 1.3486 (16) and 1.3443 (15) Å for C—O, respectively; Petek et al. (2007)]. Both molecules are not planar; the dihedral angle between the aromatic rings are 24.6 (2) and 30.30 (13) °, respectively.

Experimental

2-(4-Bromophenylimino)methyl-3,5-dimethoxyphenol was prepared by reflux a mixture of a solution containing 2-hydroxy-4, 6-dimethoxybenzaldehyde (0.02 g 0.11 mmol) in 20 ml ethanol and a solution containing 4-bromoaniline (0.019 g 0.11 mmol) in 20 ml ethanol. The reaction mixture was stirred for 1 hunder reflux. Crystals of 2-(4-Bromophenylimino)methyl-3,5-dimethoxyphenol suitable for X-ray analysis were obtained from ethylalcohol by slow evaporation (yield % 69; m.p.380–382 K).

Refinement

All H atoms bonded to C were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.93 and 0.96 Å for Camoatic-H or CmethylH, respectively. The displacement parameters of the H atoms were constrained as Uiso(H) = 1.2Ueq(Caromatic) or 1.5Ueq(Cmethyl). The positions of the hydroxyl H atoms were obtained from an electron density difference map and were refined freely.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are at the 50% probability level Dashed lines indicate intramolecular hydrogen bond.
Fig. 2.
The crystal packing of the title compound. Dashed lines indicate intramolecular hydrogen bond.

Crystal data

C15H14BrNO3Z = 4
Mr = 336.18F(000) = 680
Triclinic, P1Dx = 1.592 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2655 (5) ÅCell parameters from 26370 reflections
b = 9.7305 (6) Åθ = 2.2–29.8°
c = 18.3806 (11) ŵ = 2.94 mm1
α = 97.177 (5)°T = 296 K
β = 92.796 (5)°Plate, yellow
γ = 106.214 (5)°0.67 × 0.38 × 0.09 mm
V = 1402.94 (15) Å3

Data collection

Stoe IPDS-2 diffractometer5514 independent reflections
Radiation source: fine-focus sealed tube3901 reflections with I > 2σ(I)
plane graphiteRint = 0.080
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.2°
rotation method scansh = −10→10
Absorption correction: integration (X-RED; Stoe & Cie, 2002)k = −12→12
Tmin = 0.421, Tmax = 0.839l = −22→22
20096 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0586P)2] where P = (Fo2 + 2Fc2)/3
5514 reflections(Δ/σ)max = 0.001
369 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = −0.92 e Å3

Special details

Experimental. 360 frames, detector distance = 100 mm
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)

xyzUiso*/Ueq
H10.862 (6)0.544 (5)0.509 (3)0.086 (15)*
H40.128 (6)0.946 (5)0.005 (3)0.079 (15)*
C10.6535 (4)0.6668 (4)0.50157 (19)0.0470 (8)
C20.7277 (5)0.6064 (4)0.4429 (2)0.0542 (9)
C30.6849 (5)0.6161 (5)0.3700 (2)0.0581 (10)
H30.73310.57350.33210.070*
C40.5703 (5)0.6897 (4)0.3547 (2)0.0555 (9)
C50.4951 (5)0.7517 (4)0.4110 (2)0.0581 (10)
H50.41810.80140.39990.070*
C60.5340 (5)0.7397 (4)0.4822 (2)0.0525 (9)
C70.6914 (4)0.6516 (4)0.5757 (2)0.0486 (8)
H70.63510.68850.61240.058*
C80.8394 (4)0.5718 (4)0.66721 (19)0.0460 (8)
C90.8251 (4)0.6672 (4)0.7279 (2)0.0506 (9)
H90.78700.74640.72100.061*
C100.8666 (5)0.6459 (4)0.7981 (2)0.0503 (9)
H100.85730.71030.83840.060*
C110.9221 (4)0.5282 (4)0.80813 (19)0.0480 (8)
C120.9410 (4)0.4343 (4)0.7486 (2)0.0499 (9)
H120.98090.35620.75580.060*
C130.9008 (5)0.4565 (4)0.6792 (2)0.0522 (9)
H130.91450.39360.63910.063*
C140.5657 (6)0.6265 (6)0.2249 (2)0.0751 (12)
H14A0.52510.65140.18000.113*
H14B0.51400.52570.22690.113*
H14C0.68630.64510.22640.113*
C150.3157 (6)0.8384 (6)0.5262 (3)0.0840 (16)
H15A0.28000.87510.57160.126*
H15B0.22740.75620.50210.126*
H15C0.33940.91230.49490.126*
C160.3436 (4)0.8322 (4)−0.00258 (19)0.0472 (8)
C170.2508 (5)0.8723 (4)−0.0580 (2)0.0493 (9)
C180.2770 (5)0.8456 (4)−0.1320 (2)0.0534 (9)
H180.21470.8736−0.16790.064*
C190.3969 (5)0.7772 (4)−0.1511 (2)0.0525 (9)
C200.4941 (5)0.7381 (4)−0.0976 (2)0.0567 (10)
H200.57610.6936−0.11140.068*
C210.4692 (5)0.7651 (4)−0.0252 (2)0.0506 (9)
C220.3103 (5)0.8518 (4)0.0720 (2)0.0495 (9)
H220.37420.82280.10690.059*
C230.1593 (5)0.9256 (4)0.16780 (19)0.0485 (8)
C240.2798 (5)0.9472 (4)0.2266 (2)0.0543 (9)
H240.39050.95080.21760.065*
C250.2378 (5)0.9636 (4)0.2982 (2)0.0539 (9)
H250.31970.97920.33720.065*
C260.0739 (5)0.9566 (4)0.31126 (19)0.0511 (9)
C27−0.0479 (5)0.9373 (4)0.2532 (2)0.0528 (9)
H27−0.15830.93470.26240.063*
C28−0.0043 (5)0.9220 (4)0.1826 (2)0.0523 (9)
H28−0.08600.90890.14380.063*
C290.3267 (6)0.7663 (5)−0.2796 (2)0.0694 (12)
H29A0.36240.7342−0.32600.104*
H29B0.33820.8680−0.27550.104*
H29C0.21060.7143−0.27660.104*
C300.6916 (6)0.6705 (6)0.0127 (3)0.0811 (15)
H30A0.74150.64830.05630.122*
H30B0.77530.7407−0.00830.122*
H30C0.64990.5841−0.02230.122*
Br10.97872 (6)0.49642 (5)0.90475 (2)0.06820 (16)
Br20.01410 (7)0.97819 (6)0.40896 (2)0.07682 (18)
N10.8025 (4)0.5876 (3)0.59359 (16)0.0525 (8)
N20.1932 (4)0.9090 (3)0.09355 (16)0.0516 (7)
O10.8425 (4)0.5365 (4)0.45644 (17)0.0749 (9)
O20.5240 (4)0.7113 (3)0.28614 (15)0.0706 (8)
O30.4661 (4)0.7956 (4)0.54100 (15)0.0725 (9)
O40.1272 (4)0.9326 (3)−0.04128 (16)0.0646 (8)
O50.4290 (4)0.7403 (3)−0.22137 (15)0.0656 (7)
O60.5547 (3)0.7280 (3)0.03109 (15)0.0675 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0424 (19)0.048 (2)0.053 (2)0.0165 (18)−0.0015 (15)0.0110 (16)
C20.052 (2)0.057 (2)0.059 (2)0.022 (2)0.0009 (17)0.0162 (18)
C30.057 (2)0.070 (3)0.054 (2)0.028 (2)0.0059 (17)0.0131 (19)
C40.052 (2)0.062 (2)0.052 (2)0.014 (2)−0.0013 (17)0.0146 (18)
C50.058 (2)0.063 (2)0.060 (2)0.029 (2)−0.0084 (18)0.0120 (19)
C60.051 (2)0.056 (2)0.055 (2)0.025 (2)−0.0042 (17)0.0076 (18)
C70.045 (2)0.051 (2)0.0513 (19)0.0163 (18)−0.0007 (15)0.0080 (16)
C80.0403 (19)0.049 (2)0.0529 (19)0.0173 (17)0.0007 (15)0.0138 (16)
C90.049 (2)0.050 (2)0.060 (2)0.0242 (19)0.0024 (16)0.0118 (17)
C100.051 (2)0.049 (2)0.056 (2)0.0240 (19)0.0046 (16)0.0070 (17)
C110.0424 (19)0.052 (2)0.0510 (19)0.0137 (18)0.0001 (15)0.0143 (17)
C120.048 (2)0.049 (2)0.060 (2)0.0255 (18)−0.0012 (16)0.0111 (17)
C130.051 (2)0.053 (2)0.058 (2)0.0256 (19)−0.0006 (17)0.0040 (17)
C140.080 (3)0.094 (3)0.050 (2)0.025 (3)−0.004 (2)0.010 (2)
C150.088 (3)0.111 (4)0.079 (3)0.070 (3)0.005 (3)0.016 (3)
C160.0422 (19)0.046 (2)0.056 (2)0.0186 (18)0.0043 (16)0.0053 (16)
C170.048 (2)0.050 (2)0.055 (2)0.0199 (19)0.0128 (16)0.0100 (17)
C180.051 (2)0.062 (2)0.055 (2)0.025 (2)0.0101 (17)0.0151 (18)
C190.051 (2)0.056 (2)0.053 (2)0.0180 (19)0.0119 (17)0.0084 (17)
C200.046 (2)0.063 (2)0.067 (2)0.026 (2)0.0131 (18)0.0062 (19)
C210.045 (2)0.051 (2)0.058 (2)0.0183 (19)0.0055 (16)0.0055 (17)
C220.049 (2)0.044 (2)0.057 (2)0.0160 (18)0.0039 (17)0.0079 (16)
C230.058 (2)0.0421 (19)0.0480 (19)0.0199 (19)0.0047 (16)0.0058 (15)
C240.048 (2)0.058 (2)0.059 (2)0.020 (2)0.0014 (17)0.0056 (18)
C250.059 (2)0.058 (2)0.048 (2)0.024 (2)−0.0044 (17)0.0058 (17)
C260.070 (3)0.045 (2)0.0426 (18)0.025 (2)0.0040 (17)0.0030 (15)
C270.052 (2)0.062 (2)0.051 (2)0.031 (2)0.0032 (16)0.0036 (17)
C280.052 (2)0.056 (2)0.056 (2)0.030 (2)−0.0013 (17)0.0026 (17)
C290.071 (3)0.092 (3)0.050 (2)0.032 (3)0.0124 (19)0.006 (2)
C300.073 (3)0.104 (4)0.084 (3)0.059 (3)−0.002 (2)0.002 (3)
Br10.0863 (3)0.0739 (3)0.0528 (2)0.0335 (3)−0.0004 (2)0.0194 (2)
Br20.0908 (4)0.0951 (4)0.0472 (2)0.0325 (3)0.0114 (2)0.0046 (2)
N10.0512 (18)0.0610 (19)0.0530 (17)0.0257 (16)0.0020 (14)0.0166 (15)
N20.0568 (19)0.0546 (18)0.0509 (17)0.0273 (17)0.0082 (14)0.0085 (14)
O10.081 (2)0.106 (2)0.0632 (18)0.066 (2)0.0106 (15)0.0200 (17)
O20.078 (2)0.091 (2)0.0512 (15)0.0359 (18)−0.0052 (13)0.0183 (15)
O30.0772 (19)0.103 (2)0.0572 (16)0.0624 (19)−0.0024 (14)0.0064 (15)
O40.0738 (19)0.088 (2)0.0530 (16)0.0548 (18)0.0112 (14)0.0130 (15)
O50.0667 (17)0.085 (2)0.0554 (16)0.0364 (17)0.0178 (13)0.0085 (14)
O60.0665 (18)0.088 (2)0.0644 (17)0.0503 (17)0.0023 (13)0.0079 (15)

Geometric parameters (Å, °)

C1—C21.412 (5)C16—C221.412 (5)
C1—C71.418 (5)C16—C211.425 (5)
C1—C61.424 (4)C17—O41.342 (4)
C2—O11.344 (4)C17—C181.392 (5)
C2—C31.390 (5)C18—C191.376 (5)
C3—C41.375 (5)C18—H180.9300
C3—H30.9300C19—O51.356 (4)
C4—O21.358 (4)C19—C201.394 (5)
C4—C51.392 (5)C20—C211.361 (5)
C5—C61.358 (5)C20—H200.9300
C5—H50.9300C21—O61.366 (4)
C6—O31.365 (4)C22—N21.299 (4)
C7—N11.296 (4)C22—H220.9300
C7—H70.9300C23—C281.384 (5)
C8—C131.390 (4)C23—C241.387 (5)
C8—C91.392 (5)C23—N21.405 (4)
C8—N11.409 (4)C24—C251.379 (5)
C9—C101.373 (5)C24—H240.9300
C9—H90.9300C25—C261.372 (5)
C10—C111.376 (5)C25—H250.9300
C10—H100.9300C26—C271.387 (5)
C11—C121.380 (5)C26—Br21.888 (3)
C11—Br11.899 (3)C27—C281.365 (5)
C12—C131.362 (5)C27—H270.9300
C12—H120.9300C28—H280.9300
C13—H130.9300C29—O51.422 (5)
C14—O21.426 (5)C29—H29A0.9600
C14—H14A0.9600C29—H29B0.9600
C14—H14B0.9600C29—H29C0.9600
C14—H14C0.9600C30—O61.432 (4)
C15—O31.441 (4)C30—H30A0.9600
C15—H15A0.9600C30—H30B0.9600
C15—H15B0.9600C30—H30C0.9600
C15—H15C0.9600O1—H10.97 (5)
C16—C171.403 (5)O4—H40.83 (5)
C2—C1—C7121.9 (3)O4—C17—C16120.5 (3)
C2—C1—C6116.4 (3)C18—C17—C16121.9 (3)
C7—C1—C6121.7 (3)C19—C18—C17118.8 (3)
O1—C2—C3118.0 (3)C19—C18—H18120.6
O1—C2—C1120.2 (3)C17—C18—H18120.6
C3—C2—C1121.8 (3)O5—C19—C18124.2 (3)
C4—C3—C2119.2 (4)O5—C19—C20114.7 (3)
C4—C3—H3120.4C18—C19—C20121.1 (3)
C2—C3—H3120.4C21—C20—C19120.1 (3)
O2—C4—C3124.5 (4)C21—C20—H20120.0
O2—C4—C5114.7 (3)C19—C20—H20120.0
C3—C4—C5120.8 (3)C20—C21—O6124.6 (3)
C6—C5—C4120.2 (3)C20—C21—C16121.1 (3)
C6—C5—H5119.9O6—C21—C16114.3 (3)
C4—C5—H5119.9N2—C22—C16122.1 (3)
C5—C6—O3124.5 (3)N2—C22—H22119.0
C5—C6—C1121.6 (3)C16—C22—H22119.0
O3—C6—C1113.9 (3)C28—C23—C24118.5 (3)
N1—C7—C1121.7 (3)C28—C23—N2117.5 (3)
N1—C7—H7119.1C24—C23—N2124.1 (3)
C1—C7—H7119.1C25—C24—C23121.0 (3)
C13—C8—C9118.4 (3)C25—C24—H24119.5
C13—C8—N1117.3 (3)C23—C24—H24119.5
C9—C8—N1124.2 (3)C26—C25—C24119.3 (3)
C10—C9—C8120.7 (3)C26—C25—H25120.3
C10—C9—H9119.6C24—C25—H25120.3
C8—C9—H9119.6C25—C26—C27120.6 (3)
C9—C10—C11119.4 (3)C25—C26—Br2119.9 (3)
C9—C10—H10120.3C27—C26—Br2119.6 (3)
C11—C10—H10120.3C28—C27—C26119.5 (3)
C10—C11—C12120.7 (3)C28—C27—H27120.3
C10—C11—Br1119.9 (3)C26—C27—H27120.3
C12—C11—Br1119.3 (2)C27—C28—C23121.2 (3)
C13—C12—C11119.6 (3)C27—C28—H28119.4
C13—C12—H12120.2C23—C28—H28119.4
C11—C12—H12120.2O5—C29—H29A109.5
C12—C13—C8121.0 (3)O5—C29—H29B109.5
C12—C13—H13119.5H29A—C29—H29B109.5
C8—C13—H13119.5O5—C29—H29C109.5
O2—C14—H14A109.5H29A—C29—H29C109.5
O2—C14—H14B109.5H29B—C29—H29C109.5
H14A—C14—H14B109.5O6—C30—H30A109.5
O2—C14—H14C109.5O6—C30—H30B109.5
H14A—C14—H14C109.5H30A—C30—H30B109.5
H14B—C14—H14C109.5O6—C30—H30C109.5
O3—C15—H15A109.5H30A—C30—H30C109.5
O3—C15—H15B109.5H30B—C30—H30C109.5
H15A—C15—H15B109.5C7—N1—C8121.7 (3)
O3—C15—H15C109.5C22—N2—C23121.5 (3)
H15A—C15—H15C109.5C2—O1—H1108 (3)
H15B—C15—H15C109.5C4—O2—C14117.9 (3)
C17—C16—C22121.9 (3)C6—O3—C15117.3 (3)
C17—C16—C21117.0 (3)C17—O4—H4108 (3)
C22—C16—C21121.1 (3)C19—O5—C29118.4 (3)
O4—C17—C18117.5 (3)C21—O6—C30117.0 (3)
C7—C1—C2—O1−2.5 (6)C17—C18—C19—C20−1.6 (6)
C6—C1—C2—O1179.6 (4)O5—C19—C20—C21−177.8 (4)
C7—C1—C2—C3177.2 (4)C18—C19—C20—C211.2 (6)
C6—C1—C2—C3−0.7 (6)C19—C20—C21—O6178.3 (4)
O1—C2—C3—C4−178.7 (4)C19—C20—C21—C160.5 (6)
C1—C2—C3—C41.6 (6)C17—C16—C21—C20−1.6 (6)
C2—C3—C4—O2177.2 (4)C22—C16—C21—C20175.9 (4)
C2—C3—C4—C5−1.2 (6)C17—C16—C21—O6−179.7 (3)
O2—C4—C5—C6−178.7 (4)C22—C16—C21—O6−2.2 (5)
C3—C4—C5—C6−0.2 (7)C17—C16—C22—N2−0.7 (6)
C4—C5—C6—O3−179.4 (4)C21—C16—C22—N2−178.0 (4)
C4—C5—C6—C11.2 (7)C28—C23—C24—C250.6 (6)
C2—C1—C6—C5−0.7 (6)N2—C23—C24—C25179.6 (3)
C7—C1—C6—C5−178.6 (4)C23—C24—C25—C260.7 (6)
C2—C1—C6—O3179.8 (4)C24—C25—C26—C27−1.7 (6)
C7—C1—C6—O31.9 (6)C24—C25—C26—Br2179.8 (3)
C2—C1—C7—N13.5 (6)C25—C26—C27—C281.4 (6)
C6—C1—C7—N1−178.7 (4)Br2—C26—C27—C28179.9 (3)
C13—C8—C9—C10−1.6 (6)C26—C27—C28—C230.0 (6)
N1—C8—C9—C10−178.8 (4)C24—C23—C28—C27−0.9 (6)
C8—C9—C10—C11−0.3 (6)N2—C23—C28—C27−180.0 (3)
C9—C10—C11—C121.9 (6)C1—C7—N1—C8−179.6 (4)
C9—C10—C11—Br1−179.6 (3)C13—C8—N1—C7153.9 (4)
C10—C11—C12—C13−1.4 (6)C9—C8—N1—C7−28.9 (6)
Br1—C11—C12—C13−179.9 (3)C16—C22—N2—C23178.9 (4)
C11—C12—C13—C8−0.6 (6)C28—C23—N2—C22−150.7 (4)
C9—C8—C13—C122.1 (6)C24—C23—N2—C2230.3 (6)
N1—C8—C13—C12179.4 (4)C3—C4—O2—C1414.8 (6)
C22—C16—C17—O40.7 (6)C5—C4—O2—C14−166.7 (4)
C21—C16—C17—O4178.2 (4)C5—C6—O3—C1515.8 (6)
C22—C16—C17—C18−176.3 (4)C1—C6—O3—C15−164.8 (4)
C21—C16—C17—C181.2 (6)C18—C19—O5—C29−3.6 (6)
O4—C17—C18—C19−176.7 (4)C20—C19—O5—C29175.3 (4)
C16—C17—C18—C190.4 (6)C20—C21—O6—C306.8 (6)
C17—C18—C19—O5177.2 (4)C16—C21—O6—C30−175.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.97 (5)1.69 (5)2.564 (4)149 (5)
O4—H4···N20.83 (5)1.80 (5)2.564 (4)150 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2917).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Petek, H., Albayrak, Ç., Ağar, E., Ískeleli, N. O. & Şenel, İ. (2007). Acta Cryst. E63, o810–o812.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stoe & Cie (2002). X-AREA and X-RED32 Stoe & Cie, Darmstadt, Germany.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography