organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

8-Bromo-3-(4-ethyl­phen­yl)-1-phenyl-3,3a,4,9b-tetra­hydro-1H-chromeno[4,3-c]isoxazole-3a-carbo­nitrile

aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601204, India, bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram District, Chennai 603 203, Tamil Nadu, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

(Received 18 August 2013; accepted 26 August 2013; online 12 September 2013)

In the title compound, C25H21BrN2O2, the fused isoxazolidine ring adopts an envelope conformation with the N atom at the flap and the mean plane of the ring makes dihedral angles of 54.37 (12) and 87.32 (13)°, respectively, with the adjacent phenyl and benzene rings. The tetra­hydro­pyran ring has a half-chair conformation. In the crystal, mol­ecules are linked into a double-column structure along the b-axis direction through weak C—H⋯O and C—H⋯π inter­actions.

Related literature

For the biological activity of cyano­acrylates, see: Zhang et al. (2009[Zhang, D., Zhang, X. & Guo, L. (2009). Acta Cryst. E65, o90.]); Obniska et al. (2005[Obniska, J., Jurczyk, S., Zejc, A., Kaminski, K., Tatarczynska, E. & Stachowicz, K. (2005). Pharmacol. Rep. 57, 170-175.]). For related structures, see: Ye et al. (2009[Ye, Y., Shen, W.-L. & Wei, X.-W. (2009). Acta Cryst. E65, o2636.]); Suresh et al. (2012[Suresh, G., Sabari, V., Srinivasan, J., Mannickam, B. & Aravindhan, S. (2012). Acta Cryst. E68, o570.]); Kanchanadevi et al. (2013[Kanchanadevi, J., Anbalagan, G., Selvakumar, R., Bakthadoss, M., Gunasekaran, B. & Manivannan, V. (2013). Acta Cryst. E69, o1354.]).

[Scheme 1]

Experimental

Crystal data
  • C25H21BrN2O2

  • Mr = 461.35

  • Triclinic, [P \overline 1]

  • a = 9.8813 (3) Å

  • b = 9.9921 (3) Å

  • c = 11.1587 (3) Å

  • α = 94.125 (2)°

  • β = 92.196 (2)°

  • γ = 101.500 (2)°

  • V = 1075.27 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.94 mm−1

  • T = 295 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.620, Tmax = 0.748

  • 27480 measured reflections

  • 6895 independent reflections

  • 4405 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.123

  • S = 1.02

  • 6895 reflections

  • 274 parameters

  • H-atom parameters constrained

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.81 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg4 and Cg5 are the centroids of the C1–C4/C8/C9, C10–C15 and C17–C22 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11⋯O1i 0.93 2.57 3.475 (2) 165
C3—H3⋯Cg5ii 0.93 2.78 3.491 (3) 134
C5—H5BCg3i 0.97 2.86 3.730 (4) 149
C22—H22⋯Cg4iii 0.93 2.95 3.628 (3) 131
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Cyanoacrylates and its derivatives have been widely used as agrochemicals (Zhang et al., 2009) and an important intermediate in drugs synthesis (Obniska et al., 2005).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Ye et al., 2009; Suresh et al., 2012; Kanchanadevi et al., 2013). The crystal packing is controlled by weak intermolecular C—H···O and C—H···π (C3—H3···Cg5ii, C5—H5B···Cg3i and C22—H22···Cg4iii; symmetry codes as in Table 1; Cg3, Cg4 and Cg5 are the centroids of the rings defined by the atoms C1–C4/C8/C9, C10–C15 and C17–C22, respectively) interactions.

Related literature top

For the biological activity of cyanoacrylates, see: Zhang et al. (2009); Obniska et al. (2005). For related structures, see: Ye et al. (2009); Suresh et al. (2012); Kanchanadevi et al. (2013).

Experimental top

A mixture of (E)-2-[(4-bromo-2-formylphenoxy)methyl]-3-(4-ethylphenyl)acrylonitrile (2 mmol, 0.75 g) and N-phenylhydroxylamine (3 mmol, 0.33 g) in ethanol (10 ml) was refluxed for 6 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3 × 15 ml). The combined organic layer was washed with brine (3 × 15 ml) and dried over anhydrous Na2SO4, solvent was removed under reduced pressure. The crude mass was purified by column chromatography on silica gel (Acme 100–200 mesh), using ethyl acetate–hexane (1:9) to afford the pure compound as a colourless solid in 82% yield and melting point 171–173 °C.

Refinement top

H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined using riding model with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. A packing diagram of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.
8-Bromo-3-(4-ethylphenyl)-1-phenyl-3,3a,4,9b-tetrahydro-1H- chromeno[4,3-c]isoxazole-3a-carbonitrile top
Crystal data top
C25H21BrN2O2Z = 2
Mr = 461.35F(000) = 472
Triclinic, P1Dx = 1.425 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8813 (3) ÅCell parameters from 4405 reflections
b = 9.9921 (3) Åθ = 2.1–31.1°
c = 11.1587 (3) ŵ = 1.94 mm1
α = 94.125 (2)°T = 295 K
β = 92.196 (2)°Block, colourless
γ = 101.500 (2)°0.25 × 0.20 × 0.15 mm
V = 1075.27 (5) Å3
Data collection top
Bruker APEXII CCD
diffractometer
6895 independent reflections
Radiation source: fine-focus sealed tube4405 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 0 pixels mm-1θmax = 31.1°, θmin = 2.1°
ω and ϕ scansh = 1314
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.620, Tmax = 0.748l = 1615
27480 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0578P)2 + 0.3505P]
where P = (Fo2 + 2Fc2)/3
6895 reflections(Δ/σ)max = 0.001
274 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.81 e Å3
Crystal data top
C25H21BrN2O2γ = 101.500 (2)°
Mr = 461.35V = 1075.27 (5) Å3
Triclinic, P1Z = 2
a = 9.8813 (3) ÅMo Kα radiation
b = 9.9921 (3) ŵ = 1.94 mm1
c = 11.1587 (3) ÅT = 295 K
α = 94.125 (2)°0.25 × 0.20 × 0.15 mm
β = 92.196 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
6895 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4405 reflections with I > 2σ(I)
Tmin = 0.620, Tmax = 0.748Rint = 0.031
27480 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.02Δρmax = 0.54 e Å3
6895 reflectionsΔρmin = 0.81 e Å3
274 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.04591 (3)0.59905 (3)0.29647 (2)0.06392 (11)
O10.42095 (16)0.48260 (14)0.69339 (13)0.0480 (4)
O20.32836 (18)0.04730 (14)0.52461 (12)0.0479 (4)
N10.33533 (18)0.17431 (16)0.46483 (14)0.0387 (4)
C60.3363 (2)0.23582 (19)0.66704 (16)0.0366 (4)
C80.2571 (2)0.39431 (18)0.52539 (16)0.0350 (4)
N20.1838 (2)0.2514 (2)0.85005 (17)0.0566 (5)
C70.2565 (2)0.24777 (18)0.54874 (15)0.0337 (4)
H70.16110.19650.54980.040*
C160.3846 (2)0.0964 (2)0.64292 (17)0.0417 (4)
H160.48570.11460.64250.050*
C100.2740 (2)0.13817 (19)0.34525 (16)0.0366 (4)
C120.2584 (2)0.2032 (2)0.14426 (18)0.0490 (5)
H120.28160.26740.08830.059*
C170.3385 (2)0.0105 (2)0.72803 (18)0.0422 (4)
C90.1687 (2)0.4248 (2)0.43612 (17)0.0390 (4)
H90.11430.35440.38610.047*
C50.4613 (2)0.3539 (2)0.68345 (19)0.0449 (5)
H5A0.51570.34450.75540.054*
H5B0.51880.34990.61530.054*
C220.4339 (3)0.0410 (2)0.81004 (19)0.0512 (5)
H220.52630.00270.81000.061*
C250.2495 (2)0.2419 (2)0.77047 (17)0.0408 (4)
C40.3342 (2)0.50191 (19)0.60093 (17)0.0391 (4)
C150.1848 (2)0.0155 (2)0.31184 (19)0.0480 (5)
H150.15810.04730.36840.058*
C130.1712 (3)0.0798 (3)0.1099 (2)0.0544 (6)
H130.13680.05990.03050.065*
C110.3113 (2)0.2318 (2)0.26118 (17)0.0419 (4)
H110.37230.31420.28360.050*
C140.1354 (3)0.0133 (2)0.1927 (2)0.0570 (6)
H140.07720.09700.16910.068*
C30.3218 (2)0.6360 (2)0.5880 (2)0.0484 (5)
H30.37170.70650.64060.058*
C210.3925 (3)0.1363 (3)0.8921 (2)0.0663 (7)
H210.45750.15470.94770.080*
C20.2369 (3)0.6649 (2)0.4985 (2)0.0509 (5)
H20.22970.75500.48930.061*
C180.2022 (3)0.0779 (2)0.7290 (2)0.0526 (5)
H180.13690.05880.67410.063*
C10.1616 (2)0.5591 (2)0.42159 (18)0.0435 (5)
C190.1623 (3)0.1735 (3)0.8109 (3)0.0635 (7)
H190.07010.21790.81050.076*
C200.2571 (4)0.2044 (3)0.8934 (3)0.0696 (8)
C230.2127 (6)0.3092 (5)0.9833 (4)0.1272 (18)
H23A0.21320.25991.06150.153*
H23B0.11770.35400.96150.153*
C240.2878 (8)0.4092 (5)0.9959 (6)0.176 (3)
H24A0.27470.47040.92410.265*
H24B0.25730.45961.06330.265*
H24C0.38410.36781.00910.265*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0752 (2)0.07064 (18)0.05709 (16)0.03362 (14)0.00511 (12)0.02685 (12)
O10.0583 (9)0.0377 (7)0.0422 (8)0.0007 (6)0.0080 (7)0.0010 (6)
O20.0789 (11)0.0361 (7)0.0330 (7)0.0220 (7)0.0028 (7)0.0050 (5)
N10.0537 (10)0.0346 (8)0.0295 (7)0.0124 (7)0.0001 (7)0.0047 (6)
C60.0455 (11)0.0356 (9)0.0288 (8)0.0079 (8)0.0005 (7)0.0055 (7)
C80.0429 (10)0.0304 (8)0.0320 (8)0.0066 (7)0.0053 (7)0.0049 (7)
N20.0735 (14)0.0594 (12)0.0382 (9)0.0142 (10)0.0083 (9)0.0069 (8)
C70.0412 (10)0.0300 (8)0.0291 (8)0.0052 (7)0.0001 (7)0.0039 (6)
C160.0513 (12)0.0412 (10)0.0350 (9)0.0146 (9)0.0007 (8)0.0062 (8)
C100.0436 (10)0.0357 (9)0.0308 (8)0.0095 (8)0.0011 (8)0.0014 (7)
C120.0593 (13)0.0541 (12)0.0352 (10)0.0124 (10)0.0019 (9)0.0112 (9)
C170.0581 (13)0.0356 (9)0.0366 (9)0.0177 (9)0.0012 (9)0.0050 (7)
C90.0456 (11)0.0371 (9)0.0358 (9)0.0106 (8)0.0040 (8)0.0054 (7)
C50.0453 (11)0.0463 (11)0.0409 (10)0.0058 (9)0.0069 (9)0.0043 (8)
C220.0624 (14)0.0549 (12)0.0409 (11)0.0214 (11)0.0019 (10)0.0099 (9)
C250.0541 (12)0.0369 (9)0.0306 (9)0.0073 (9)0.0022 (8)0.0062 (7)
C40.0460 (11)0.0349 (9)0.0349 (9)0.0039 (8)0.0063 (8)0.0034 (7)
C150.0581 (13)0.0408 (11)0.0420 (11)0.0018 (9)0.0013 (10)0.0070 (8)
C130.0632 (15)0.0609 (14)0.0367 (10)0.0113 (12)0.0076 (10)0.0032 (10)
C110.0499 (12)0.0375 (10)0.0362 (9)0.0035 (8)0.0011 (8)0.0049 (8)
C140.0661 (15)0.0468 (12)0.0502 (12)0.0016 (11)0.0082 (11)0.0059 (10)
C30.0578 (13)0.0316 (9)0.0534 (12)0.0043 (9)0.0090 (10)0.0021 (8)
C210.090 (2)0.0736 (17)0.0475 (13)0.0376 (15)0.0040 (13)0.0240 (12)
C20.0689 (15)0.0333 (10)0.0554 (12)0.0172 (10)0.0163 (11)0.0099 (9)
C180.0597 (14)0.0463 (12)0.0552 (13)0.0176 (10)0.0010 (11)0.0091 (10)
C10.0510 (12)0.0446 (11)0.0412 (10)0.0192 (9)0.0118 (9)0.0144 (8)
C190.0729 (17)0.0464 (12)0.0751 (17)0.0147 (12)0.0211 (14)0.0150 (12)
C200.101 (2)0.0574 (14)0.0624 (15)0.0338 (15)0.0275 (15)0.0264 (12)
C230.182 (5)0.104 (3)0.122 (3)0.057 (3)0.067 (3)0.080 (3)
C240.283 (8)0.101 (3)0.174 (5)0.071 (4)0.070 (5)0.086 (4)
Geometric parameters (Å, º) top
Br1—C11.886 (2)C5—H5B0.9700
O1—C41.365 (3)C22—C211.382 (3)
O1—C51.418 (3)C22—H220.9300
O2—C161.426 (2)C4—C31.386 (3)
O2—N11.467 (2)C15—C141.388 (3)
N1—C101.435 (2)C15—H150.9300
N1—C71.485 (2)C13—C141.365 (4)
C6—C251.469 (3)C13—H130.9300
C6—C51.524 (3)C11—H110.9300
C6—C71.536 (2)C14—H140.9300
C6—C161.569 (3)C3—C21.363 (3)
C8—C91.389 (3)C3—H30.9300
C8—C41.393 (3)C21—C201.376 (4)
C8—C71.505 (2)C21—H210.9300
N2—C251.130 (3)C2—C11.384 (3)
C7—H70.9800C2—H20.9300
C16—C171.495 (3)C18—C191.381 (3)
C16—H160.9800C18—H180.9300
C10—C151.377 (3)C19—C201.382 (4)
C10—C111.381 (3)C19—H190.9300
C12—C131.375 (3)C20—C231.516 (4)
C12—C111.376 (3)C23—C241.371 (6)
C12—H120.9300C23—H23A0.9700
C17—C181.381 (3)C23—H23B0.9700
C17—C221.382 (3)C24—H24A0.9600
C9—C11.379 (3)C24—H24B0.9600
C9—H90.9300C24—H24C0.9600
C5—H5A0.9700
C4—O1—C5114.15 (15)O1—C4—C3116.29 (18)
C16—O2—N1102.54 (13)O1—C4—C8122.97 (17)
C10—N1—O2107.73 (14)C3—C4—C8120.7 (2)
C10—N1—C7115.95 (15)C10—C15—C14119.2 (2)
O2—N1—C799.71 (13)C10—C15—H15120.4
C25—C6—C5109.23 (16)C14—C15—H15120.4
C25—C6—C7111.41 (16)C14—C13—C12119.8 (2)
C5—C6—C7108.42 (15)C14—C13—H13120.1
C25—C6—C16114.63 (16)C12—C13—H13120.1
C5—C6—C16110.13 (17)C12—C11—C10120.00 (19)
C7—C6—C16102.74 (14)C12—C11—H11120.0
C9—C8—C4118.41 (17)C10—C11—H11120.0
C9—C8—C7120.38 (17)C13—C14—C15120.8 (2)
C4—C8—C7120.82 (17)C13—C14—H14119.6
N1—C7—C8115.44 (15)C15—C14—H14119.6
N1—C7—C698.84 (14)C2—C3—C4120.4 (2)
C8—C7—C6112.34 (15)C2—C3—H3119.8
N1—C7—H7109.9C4—C3—H3119.8
C8—C7—H7109.9C20—C21—C22121.5 (2)
C6—C7—H7109.9C20—C21—H21119.3
O2—C16—C17109.47 (17)C22—C21—H21119.3
O2—C16—C6104.02 (15)C3—C2—C1119.47 (19)
C17—C16—C6116.39 (16)C3—C2—H2120.3
O2—C16—H16108.9C1—C2—H2120.3
C17—C16—H16108.9C17—C18—C19120.5 (2)
C6—C16—H16108.9C17—C18—H18119.7
C15—C10—C11120.04 (18)C19—C18—H18119.7
C15—C10—N1123.18 (17)C9—C1—C2120.9 (2)
C11—C10—N1116.75 (17)C9—C1—Br1119.56 (16)
C13—C12—C11120.2 (2)C2—C1—Br1119.56 (15)
C13—C12—H12119.9C18—C19—C20121.1 (3)
C11—C12—H12119.9C18—C19—H19119.5
C18—C17—C22118.8 (2)C20—C19—H19119.5
C18—C17—C16121.91 (19)C21—C20—C19118.0 (2)
C22—C17—C16119.3 (2)C21—C20—C23121.1 (3)
C1—C9—C8120.11 (19)C19—C20—C23120.9 (3)
C1—C9—H9119.9C24—C23—C20118.3 (4)
C8—C9—H9119.9C24—C23—H23A107.7
O1—C5—C6111.55 (17)C20—C23—H23A107.7
O1—C5—H5A109.3C24—C23—H23B107.7
C6—C5—H5A109.3C20—C23—H23B107.7
O1—C5—H5B109.3H23A—C23—H23B107.1
C6—C5—H5B109.3C23—C24—H24A109.5
H5A—C5—H5B108.0C23—C24—H24B109.5
C17—C22—C21120.2 (2)H24A—C24—H24B109.5
C17—C22—H22119.9C23—C24—H24C109.5
C21—C22—H22119.9H24A—C24—H24C109.5
N2—C25—C6177.6 (2)H24B—C24—H24C109.5
C16—O2—N1—C10176.95 (16)C7—C6—C5—O162.4 (2)
C16—O2—N1—C755.56 (17)C16—C6—C5—O1174.11 (15)
C10—N1—C7—C872.5 (2)C18—C17—C22—C210.7 (3)
O2—N1—C7—C8172.22 (15)C16—C17—C22—C21177.9 (2)
C10—N1—C7—C6167.50 (15)C5—O1—C4—C3162.91 (18)
O2—N1—C7—C652.22 (15)C5—O1—C4—C819.5 (3)
C9—C8—C7—N180.4 (2)C9—C8—C4—O1178.12 (18)
C4—C8—C7—N1106.9 (2)C7—C8—C4—O15.2 (3)
C9—C8—C7—C6167.34 (17)C9—C8—C4—C30.7 (3)
C4—C8—C7—C65.4 (3)C7—C8—C4—C3172.24 (18)
C25—C6—C7—N1154.08 (15)C11—C10—C15—C141.0 (3)
C5—C6—C7—N185.69 (17)N1—C10—C15—C14177.1 (2)
C16—C6—C7—N130.87 (17)C11—C12—C13—C141.2 (4)
C25—C6—C7—C883.6 (2)C13—C12—C11—C101.8 (3)
C5—C6—C7—C836.6 (2)C15—C10—C11—C120.7 (3)
C16—C6—C7—C8153.14 (16)N1—C10—C11—C12178.96 (19)
N1—O2—C16—C17158.99 (16)C12—C13—C14—C150.6 (4)
N1—O2—C16—C633.95 (19)C10—C15—C14—C131.7 (4)
C25—C6—C16—O2119.69 (18)O1—C4—C3—C2179.65 (19)
C5—C6—C16—O2116.68 (17)C8—C4—C3—C22.0 (3)
C7—C6—C16—O21.34 (19)C17—C22—C21—C201.0 (4)
C25—C6—C16—C170.8 (3)C4—C3—C2—C10.9 (3)
C5—C6—C16—C17122.83 (19)C22—C17—C18—C190.3 (3)
C7—C6—C16—C17121.83 (18)C16—C17—C18—C19178.3 (2)
O2—N1—C10—C1520.2 (3)C8—C9—C1—C23.0 (3)
C7—N1—C10—C1590.5 (2)C8—C9—C1—Br1177.82 (14)
O2—N1—C10—C11158.00 (17)C3—C2—C1—C91.6 (3)
C7—N1—C10—C1191.4 (2)C3—C2—C1—Br1179.19 (17)
O2—C16—C17—C1847.1 (3)C17—C18—C19—C200.1 (4)
C6—C16—C17—C1870.4 (3)C22—C21—C20—C190.9 (4)
O2—C16—C17—C22134.4 (2)C22—C21—C20—C23179.7 (3)
C6—C16—C17—C22108.1 (2)C18—C19—C20—C210.4 (4)
C4—C8—C9—C11.8 (3)C18—C19—C20—C23179.8 (3)
C7—C8—C9—C1174.74 (17)C21—C20—C23—C2449.4 (7)
C4—O1—C5—C654.0 (2)C19—C20—C23—C24131.2 (5)
C25—C6—C5—O159.2 (2)
Hydrogen-bond geometry (Å, º) top
Cg3, Cg4 and Cg5 are the centroids of the C1–C4/C8/C9, C10–C15 and C17–C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.932.573.475 (2)165
C3—H3···Cg5ii0.932.783.491 (3)134
C5—H5B···Cg3i0.972.863.730 (4)149
C22—H22···Cg4iii0.932.953.628 (3)131
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z; (iii) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
Cg3, Cg4 and Cg5 are the centroids of the C1–C4/C8/C9, C10–C15 and C17–C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.932.573.475 (2)165
C3—H3···Cg5ii0.932.783.491 (3)134
C5—H5B···Cg3i0.972.863.730 (4)149
C22—H22···Cg4iii0.932.953.628 (3)131
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z; (iii) x+1, y, z+1.
 

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