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Acta Cryst. (2007). E63, o2948    [ doi:10.1107/S1600536807024348 ]

2-Bromo-N'-[(E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate

B. Narayana, K. Sunil, H. S. Yathirajan, B. K. Sarojini and M. Bolte

Abstract top

The crystal packing of the title compound, C15H12BrFN2O2·H2O, is stabilized by N-H...O and O-H...O hydrogen bonds. There are two molecules in the asymmetric unit, differing in the dihedral angle between the two aromatic rings, which are 62.3 (2) and 49.9 (2)°.

Comment top

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives were reported to possess antimicrobial, anti-inflammatory and central nervous system activities. Moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor, and as herbicides. A new Schiff base, (I), C15H12BrFN2O2.H2O is synthesized and its crystal structure is reported.

The two molecules in the asymmetric unit differ in the dihedral angle between the two aromatic rings, which are 62.3 (2)° and 49.9 (2)°. The crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds.

Related literature top

For related structures, see: 2'-[1-(4-fluorophenyl)ethyl]isonicotino-KN-hydrazide-cyanoborane (Bruno et al., 1998); 1-(2-bromo-5-methoxyphenyl)-8-chloro-6-(2-fluorophenyl)-4H-1,2,4-triazolo[4,3-a] [1,4]benzodiazepine (Harrison et al., 2005); 2-bromo-5-methoxy-N'-[(E)-(2-nitrophenyl)methylene]benzohydrazide (Yathirajan, Sarojini et al., 2007); N'-[(1E)-(4-fluorophenyl)methylene]-6-methoxy-2-naphthohydrazide (Yathirajan, Narayana, et al., 2007). For related literature, see: Varma et al. (1986); Misra et al. (1981); Agarwal et al. (1983); Singh et al. (1988); Hodnett et al. (1970).

Experimental top

A mixture of 2-bromo-5-methoxybenzohydrazide (0.735 g, 0.003 mol) and 4-fluorobenzaldehyde (0.372 g, 0.003 mol) in 15 ml of absolute alcohol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h (see scheme). On cooling, the solid separated was filtered off and recrystallized from ethyl acetate (m.p.: 440–442 K). Analysis for C15H12BrFN2O2.H2O: Found (calculated): C 48.71 (48.80), H 3.76 (3.82), N 7.51 (7.59) %.

Refinement top

H atoms were found in a difference map, but they were refined using a riding model with C—H = 0.95 Å, N—H = 0.88 Å, O—H = 0.84Å and Uiso(H) = 1.2Ueq(C,N,O) or C—H = 0.98Å and Uiso(H) = 1.5Ueq(Cmethyl).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The structure of the two independent molecules in the asymmetric unit of the title compound, with the atom numbering. Displacement ellipsoids are at the 50% probability level.
2-Bromo-N'-[(1E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate top
Crystal data top
C15H12BrFN2O2.H2OF(000) = 1488
Mr = 369.19Dx = 1.625 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 11319 reflections
a = 30.1171 (18) Åθ = 3.6–25.1°
b = 8.0187 (7) ŵ = 2.75 mm−1
c = 13.4661 (8) ÅT = 173 K
β = 111.902 (4)°Block, colourless
V = 3017.3 (4) Å30.37 × 0.35 × 0.33 mm
Z = 8
Data collection top
STOE IPDS II two-circle-
diffractometer		5477 independent reflections
Radiation source: fine-focus sealed tube4843 reflections with I > 2σ(I)
graphiteRint = 0.059
ω scansθmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)		h = −36→35
Tmin = 0.379, Tmax = 0.394k = −9→9
16531 measured reflectionsl = −16→16
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.080 w = 1/[σ2(Fo2) + (0.163P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.202(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.56 e Å−3
5477 reflectionsΔρmin = −0.76 e Å−3
400 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0062 (8)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2642 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.018 (17)
Crystal data top
C15H12BrFN2O2.H2OV = 3017.3 (4) Å3
Mr = 369.19Z = 8
Monoclinic, CcMo Kα radiation
a = 30.1171 (18) ŵ = 2.75 mm−1
b = 8.0187 (7) ÅT = 173 K
c = 13.4661 (8) Å0.37 × 0.35 × 0.33 mm
β = 111.902 (4)°
Data collection top
STOE IPDS II two-circle-
diffractometer		5477 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)		4843 reflections with I > 2σ(I)
Tmin = 0.379, Tmax = 0.394Rint = 0.059
16531 measured reflectionsθmax = 25.6°
Refinement top
R[F2 > 2σ(F2)] = 0.080H-atom parameters constrained
wR(F2) = 0.202Δρmax = 0.56 e Å−3
S = 1.02Δρmin = −0.76 e Å−3
5477 reflectionsAbsolute structure: Flack (1983), 2642 Friedel pairs
400 parametersFlack parameter: 0.018 (17)
2 restraints
Special details top

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) top
xyzUiso*/Ueq
Br10.52393 (3)0.24296 (11)0.77882 (6)0.0677 (3)
F10.82483 (19)0.6614 (8)0.6074 (5)0.0838 (15)
O10.5622 (2)0.5636 (7)0.6968 (4)0.0603 (12)
O20.3807 (2)0.4246 (8)0.3428 (5)0.0697 (14)
N10.5647 (3)0.4797 (9)0.5375 (5)0.0578 (14)
H10.54990.43120.47520.069*
N20.6106 (2)0.5460 (8)0.5654 (5)0.0548 (13)
C10.5439 (3)0.4937 (9)0.6110 (6)0.0557 (15)
C20.6317 (3)0.5090 (10)0.5039 (7)0.0594 (17)
H20.61530.44750.44040.071*
C110.4947 (3)0.4167 (8)0.5755 (6)0.0540 (15)
C120.4806 (3)0.3189 (9)0.6429 (5)0.0555 (15)
C130.4333 (3)0.2595 (9)0.6109 (7)0.0584 (17)
H130.42370.19140.65710.070*
C140.4013 (3)0.3030 (12)0.5107 (7)0.0623 (19)
H140.36890.26800.48930.075*
C150.4150 (3)0.3964 (10)0.4402 (7)0.0605 (17)
C160.4613 (3)0.4553 (9)0.4731 (6)0.0568 (16)
H160.47070.52220.42610.068*
C170.3953 (3)0.5087 (12)0.2651 (7)0.070 (2)
H17A0.40900.61760.29330.105*
H17B0.36740.52430.19860.105*
H17C0.41930.44120.25060.105*
C210.6819 (3)0.5605 (10)0.5292 (6)0.0554 (15)
C220.7068 (3)0.4959 (10)0.4660 (7)0.0625 (17)
H220.69010.42970.40490.075*
C230.7554 (3)0.5292 (11)0.4933 (7)0.0629 (18)
H230.77250.48470.45280.076*
C240.7774 (3)0.6282 (11)0.5806 (7)0.0648 (19)
C250.7545 (3)0.6977 (11)0.6432 (7)0.0661 (18)
H250.77120.76840.70190.079*
C260.7071 (3)0.6607 (9)0.6175 (6)0.0583 (16)
H260.69100.70390.66050.070*
Br1A0.15181 (3)0.26881 (10)0.25235 (4)0.0646 (3)
C1A0.1256 (3)0.4374 (10)0.0114 (6)0.0569 (16)
F1A−0.1718 (2)0.6188 (9)−0.1250 (5)0.0903 (17)
O1A0.1093 (2)0.3990 (7)−0.0840 (4)0.0620 (12)
O2A0.2918 (2)0.3916 (8)0.0344 (5)0.0682 (14)
N1A0.0998 (2)0.5084 (9)0.0612 (5)0.0583 (14)
H1A0.11350.54700.12680.070*
N2A0.0509 (3)0.5199 (8)0.0075 (5)0.0576 (15)
C2A0.0269 (3)0.5737 (10)0.0615 (6)0.0597 (16)
H2A0.04300.60680.13390.072*
C11A0.1769 (3)0.3985 (8)0.0781 (6)0.0543 (15)
C12A0.1936 (3)0.3191 (9)0.1777 (6)0.0551 (15)
C13A0.2403 (3)0.2667 (10)0.2268 (7)0.0604 (17)
H13A0.25040.21180.29410.072*
C14A0.2724 (3)0.2947 (10)0.1770 (8)0.0645 (18)
H14A0.30480.26010.21080.077*
C15A0.2577 (3)0.3727 (10)0.0784 (6)0.0606 (16)
C16A0.2104 (3)0.4230 (10)0.0277 (6)0.0565 (16)
H16A0.20040.4739−0.04090.068*
C17A0.2772 (3)0.4652 (12)−0.0697 (7)0.071 (2)
H17D0.25070.4004−0.12000.107*
H17E0.30420.4654−0.09360.107*
H17F0.26660.5800−0.06670.107*
C21A−0.0256 (3)0.5847 (10)0.0117 (7)0.0625 (18)
C22A−0.0509 (3)0.6564 (10)0.0689 (8)0.0665 (18)
H22A−0.03430.69580.13970.080*
C23A−0.1008 (3)0.6706 (12)0.0220 (9)0.073 (2)
H23A−0.11850.72230.05900.088*
C24A−0.1232 (3)0.6070 (13)−0.0792 (8)0.077 (2)
C25A−0.0994 (3)0.5372 (13)−0.1390 (8)0.073 (2)
H25A−0.11630.5000−0.21010.088*
C26A−0.0501 (3)0.5231 (9)−0.0922 (7)0.0611 (17)
H26A−0.03280.4717−0.13020.073*
O1W0.5235 (2)0.2938 (8)0.3394 (5)0.0634 (12)
H1W10.53490.33600.29690.076*
H1W20.54880.23720.36190.076*
O1WA0.1404 (2)0.7000 (7)0.2531 (4)0.0585 (12)
H1W30.11780.76860.23670.070*
H1W40.13110.67030.30200.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0677 (5)0.0716 (5)0.0613 (5)−0.0041 (4)0.0213 (4)0.0093 (3)
F10.055 (3)0.098 (4)0.102 (4)−0.007 (2)0.033 (3)0.007 (3)
O10.059 (3)0.067 (3)0.060 (3)−0.003 (2)0.027 (2)−0.004 (2)
O20.056 (3)0.081 (4)0.068 (3)−0.003 (3)0.019 (3)0.005 (3)
N10.057 (4)0.059 (3)0.055 (3)−0.004 (3)0.018 (3)−0.004 (3)
N20.051 (3)0.057 (3)0.055 (3)0.001 (2)0.019 (3)0.001 (2)
C10.057 (4)0.053 (3)0.057 (4)0.000 (3)0.020 (3)−0.003 (3)
C20.058 (4)0.055 (4)0.060 (4)0.001 (3)0.017 (3)0.001 (3)
C110.049 (4)0.048 (3)0.068 (4)0.002 (3)0.025 (3)−0.003 (3)
C120.056 (4)0.060 (4)0.045 (3)0.007 (3)0.013 (3)0.002 (3)
C130.063 (4)0.055 (4)0.065 (4)−0.003 (3)0.032 (4)−0.003 (3)
C140.050 (4)0.066 (5)0.076 (5)−0.002 (3)0.029 (4)−0.006 (3)
C150.062 (4)0.054 (4)0.066 (4)0.000 (3)0.025 (4)−0.004 (3)
C160.065 (4)0.051 (3)0.061 (4)−0.004 (3)0.032 (3)0.001 (3)
C170.062 (5)0.079 (5)0.061 (4)−0.004 (4)0.015 (4)0.003 (4)
C210.054 (4)0.057 (4)0.058 (4)0.003 (3)0.024 (3)0.010 (3)
C220.071 (5)0.055 (4)0.062 (4)−0.002 (3)0.025 (4)0.004 (3)
C230.062 (4)0.067 (4)0.071 (4)0.007 (3)0.038 (4)0.007 (3)
C240.058 (4)0.070 (5)0.070 (4)0.003 (3)0.029 (4)0.017 (4)
C250.066 (5)0.064 (4)0.063 (4)−0.006 (4)0.018 (4)0.006 (3)
C260.058 (4)0.056 (4)0.067 (4)0.005 (3)0.030 (3)0.007 (3)
Br1A0.0716 (5)0.0638 (4)0.0619 (5)0.0006 (4)0.0291 (4)0.0058 (4)
C1A0.058 (4)0.052 (4)0.060 (4)−0.001 (3)0.021 (3)0.001 (3)
F1A0.059 (3)0.117 (5)0.097 (4)0.014 (3)0.031 (3)0.027 (3)
O1A0.055 (3)0.076 (3)0.053 (2)0.003 (2)0.019 (2)−0.004 (2)
O2A0.055 (3)0.073 (3)0.077 (4)0.001 (3)0.026 (3)−0.001 (3)
N1A0.055 (3)0.061 (3)0.056 (3)0.001 (3)0.018 (3)−0.005 (2)
N2A0.056 (4)0.057 (3)0.058 (3)0.000 (3)0.018 (3)−0.001 (3)
C2A0.059 (4)0.053 (4)0.063 (4)0.003 (3)0.018 (3)0.002 (3)
C11A0.054 (4)0.048 (3)0.061 (4)−0.001 (3)0.022 (3)−0.002 (3)
C12A0.058 (4)0.056 (3)0.058 (4)−0.004 (3)0.029 (3)0.000 (3)
C13A0.062 (5)0.060 (4)0.054 (4)0.007 (3)0.017 (3)0.000 (3)
C14A0.059 (4)0.056 (4)0.074 (5)0.004 (3)0.019 (4)−0.006 (3)
C15A0.057 (4)0.058 (4)0.068 (4)−0.002 (3)0.025 (3)−0.010 (3)
C16A0.058 (4)0.054 (4)0.054 (3)−0.001 (3)0.017 (3)−0.004 (3)
C17A0.069 (5)0.075 (5)0.074 (5)0.000 (4)0.031 (4)0.000 (4)
C21A0.059 (4)0.055 (4)0.074 (5)0.002 (3)0.026 (4)0.003 (3)
C22A0.065 (5)0.061 (4)0.079 (5)−0.001 (3)0.033 (4)−0.001 (3)
C23A0.071 (5)0.055 (4)0.106 (7)0.007 (3)0.046 (5)0.009 (4)
C24A0.059 (5)0.087 (6)0.085 (6)0.003 (4)0.026 (4)0.021 (5)
C25A0.062 (5)0.087 (6)0.072 (5)−0.009 (4)0.027 (4)0.004 (4)
C26A0.061 (4)0.057 (4)0.069 (4)0.005 (3)0.029 (4)0.012 (3)
O1W0.062 (3)0.067 (3)0.062 (3)0.002 (2)0.023 (3)−0.003 (2)
O1WA0.060 (3)0.060 (3)0.057 (3)0.006 (2)0.023 (2)0.004 (2)
Geometric parameters (Å, °) top
Br1—C121.908 (7)C1A—N1A1.331 (11)
F1—C241.363 (10)C1A—C11A1.501 (11)
O1—C11.216 (9)F1A—C24A1.363 (11)
O2—C151.352 (11)O2A—C15A1.371 (10)
O2—C171.444 (11)O2A—C17A1.431 (11)
N1—C11.358 (10)N1A—N2A1.378 (10)
N1—N21.396 (10)N1A—H1A0.8800
N1—H10.8800N2A—C2A1.276 (11)
N2—C21.254 (11)C2A—C21A1.474 (12)
C1—C111.510 (10)C2A—H2A0.9500
C2—C211.480 (12)C11A—C12A1.398 (10)
C2—H20.9500C11A—C16A1.425 (11)
C11—C121.381 (11)C12A—C13A1.380 (12)
C11—C161.405 (11)C13A—C14A1.385 (14)
C12—C131.408 (12)C13A—H13A0.9500
C13—C141.379 (13)C14A—C15A1.382 (13)
C13—H130.9500C14A—H14A0.9500
C14—C151.386 (12)C15A—C16A1.390 (12)
C14—H140.9500C16A—H16A0.9500
C15—C161.380 (11)C17A—H17D0.9800
C16—H160.9500C17A—H17E0.9800
C17—H17A0.9800C17A—H17F0.9800
C17—H17B0.9800C21A—C22A1.393 (12)
C17—H17C0.9800C21A—C26A1.405 (12)
C21—C261.401 (12)C22A—C23A1.400 (13)
C21—C221.423 (12)C22A—H22A0.9500
C22—C231.396 (13)C23A—C24A1.373 (16)
C22—H220.9500C23A—H23A0.9500
C23—C241.368 (13)C24A—C25A1.382 (15)
C23—H230.9500C25A—C26A1.384 (13)
C24—C251.389 (13)C25A—H25A0.9500
C25—C261.370 (12)C26A—H26A0.9500
C25—H250.9500O1W—H1W10.8401
C26—H260.9500O1W—H1W20.8424
Br1A—C12A1.923 (7)O1WA—H1W30.8399
C1A—O1A1.231 (10)O1WA—H1W40.8400
C15—O2—C17116.9 (6)O1A—C1A—C11A119.5 (7)
C1—N1—N2116.9 (6)N1A—C1A—C11A116.8 (7)
C1—N1—H1121.6C15A—O2A—C17A117.5 (7)
N2—N1—H1121.6C1A—N1A—N2A118.3 (7)
C2—N2—N1115.4 (7)C1A—N1A—H1A120.8
O1—C1—N1124.3 (7)N2A—N1A—H1A120.8
O1—C1—C11122.1 (7)C2A—N2A—N1A116.4 (7)
N1—C1—C11113.6 (6)N2A—C2A—C21A120.1 (7)
N2—C2—C21120.6 (8)N2A—C2A—H2A120.0
N2—C2—H2119.7C21A—C2A—H2A120.0
C21—C2—H2119.7C12A—C11A—C16A117.0 (7)
C12—C11—C16119.2 (7)C12A—C11A—C1A126.2 (7)
C12—C11—C1122.1 (7)C16A—C11A—C1A116.1 (6)
C16—C11—C1118.6 (6)C13A—C12A—C11A122.4 (7)
C11—C12—C13121.0 (7)C13A—C12A—Br1A115.8 (6)
C11—C12—Br1122.9 (6)C11A—C12A—Br1A121.7 (6)
C13—C12—Br1116.0 (6)C12A—C13A—C14A119.4 (8)
C14—C13—C12118.2 (7)C12A—C13A—H13A120.3
C14—C13—H13120.9C14A—C13A—H13A120.3
C12—C13—H13120.9C15A—C14A—C13A120.4 (8)
C13—C14—C15121.9 (7)C15A—C14A—H14A119.8
C13—C14—H14119.0C13A—C14A—H14A119.8
C15—C14—H14119.0O2A—C15A—C14A116.1 (8)
O2—C15—C16124.6 (7)O2A—C15A—C16A123.4 (7)
O2—C15—C14116.2 (7)C14A—C15A—C16A120.4 (8)
C16—C15—C14119.2 (7)C15A—C16A—C11A120.3 (7)
C15—C16—C11120.4 (7)C15A—C16A—H16A119.9
C15—C16—H16119.8C11A—C16A—H16A119.9
C11—C16—H16119.8O2A—C17A—H17D109.5
O2—C17—H17A109.5O2A—C17A—H17E109.5
O2—C17—H17B109.5H17D—C17A—H17E109.5
H17A—C17—H17B109.5O2A—C17A—H17F109.5
O2—C17—H17C109.5H17D—C17A—H17F109.5
H17A—C17—H17C109.5H17E—C17A—H17F109.5
H17B—C17—H17C109.5C22A—C21A—C26A120.3 (8)
C26—C21—C22118.6 (7)C22A—C21A—C2A119.2 (8)
C26—C21—C2122.6 (7)C26A—C21A—C2A120.5 (7)
C22—C21—C2118.7 (8)C21A—C22A—C23A120.0 (9)
C23—C22—C21120.4 (8)C21A—C22A—H22A120.0
C23—C22—H22119.8C23A—C22A—H22A120.0
C21—C22—H22119.8C24A—C23A—C22A117.8 (9)
C24—C23—C22117.5 (8)C24A—C23A—H23A121.1
C24—C23—H23121.3C22A—C23A—H23A121.1
C22—C23—H23121.3F1A—C24A—C23A118.1 (9)
F1—C24—C23117.7 (8)F1A—C24A—C25A117.9 (9)
F1—C24—C25117.9 (8)C23A—C24A—C25A123.9 (9)
C23—C24—C25124.3 (8)C24A—C25A—C26A118.1 (9)
C26—C25—C24117.7 (8)C24A—C25A—H25A121.0
C26—C25—H25121.1C26A—C25A—H25A121.0
C24—C25—H25121.1C25A—C26A—C21A119.9 (8)
C25—C26—C21121.5 (7)C25A—C26A—H26A120.0
C25—C26—H26119.3C21A—C26A—H26A120.0
C21—C26—H26119.3H1W1—O1W—H1W285.1
O1A—C1A—N1A123.6 (8)H1W3—O1WA—H1W485.2
C1—N1—N2—C2169.4 (7)O1A—C1A—N1A—N2A8.9 (12)
N2—N1—C1—O12.2 (11)C11A—C1A—N1A—N2A−169.1 (6)
N2—N1—C1—C11−179.1 (6)C1A—N1A—N2A—C2A173.4 (7)
N1—N2—C2—C21−175.2 (6)N1A—N2A—C2A—C21A−177.9 (7)
O1—C1—C11—C12−45.4 (10)O1A—C1A—C11A—C12A−130.6 (8)
N1—C1—C11—C12135.9 (7)N1A—C1A—C11A—C12A47.4 (11)
O1—C1—C11—C16130.4 (8)O1A—C1A—C11A—C16A39.6 (10)
N1—C1—C11—C16−48.4 (9)N1A—C1A—C11A—C16A−142.4 (7)
C16—C11—C12—C13−0.8 (10)C16A—C11A—C12A—C13A0.3 (11)
C1—C11—C12—C13174.9 (7)C1A—C11A—C12A—C13A170.5 (7)
C16—C11—C12—Br1174.6 (5)C16A—C11A—C12A—Br1A−177.3 (5)
C1—C11—C12—Br1−9.7 (10)C1A—C11A—C12A—Br1A−7.1 (10)
C11—C12—C13—C14−0.6 (11)C11A—C12A—C13A—C14A0.8 (12)
Br1—C12—C13—C14−176.3 (6)Br1A—C12A—C13A—C14A178.5 (6)
C12—C13—C14—C152.8 (12)C12A—C13A—C14A—C15A−0.8 (12)
C17—O2—C15—C166.1 (12)C17A—O2A—C15A—C14A177.3 (7)
C17—O2—C15—C14−174.6 (8)C17A—O2A—C15A—C16A−0.8 (11)
C13—C14—C15—O2177.2 (7)C13A—C14A—C15A—O2A−178.6 (7)
C13—C14—C15—C16−3.5 (13)C13A—C14A—C15A—C16A−0.4 (12)
O2—C15—C16—C11−178.8 (7)O2A—C15A—C16A—C11A179.6 (7)
C14—C15—C16—C111.9 (12)C14A—C15A—C16A—C11A1.6 (11)
C12—C11—C16—C150.2 (11)C12A—C11A—C16A—C15A−1.6 (10)
C1—C11—C16—C15−175.7 (7)C1A—C11A—C16A—C15A−172.7 (7)
N2—C2—C21—C26−4.3 (12)N2A—C2A—C21A—C22A−174.8 (8)
N2—C2—C21—C22171.0 (7)N2A—C2A—C21A—C26A5.4 (12)
C26—C21—C22—C231.4 (11)C26A—C21A—C22A—C23A−1.4 (12)
C2—C21—C22—C23−174.1 (7)C2A—C21A—C22A—C23A178.8 (8)
C21—C22—C23—C24−1.5 (12)C21A—C22A—C23A—C24A2.0 (13)
C22—C23—C24—F1−179.8 (7)C22A—C23A—C24A—F1A179.4 (8)
C22—C23—C24—C25−0.2 (13)C22A—C23A—C24A—C25A−3.1 (14)
F1—C24—C25—C26−178.5 (7)F1A—C24A—C25A—C26A−179.1 (8)
C23—C24—C25—C261.9 (13)C23A—C24A—C25A—C26A3.3 (15)
C24—C25—C26—C21−1.9 (12)C24A—C25A—C26A—C21A−2.4 (13)
C22—C21—C26—C250.4 (11)C22A—C21A—C26A—C25A1.6 (12)
C2—C21—C26—C25175.7 (7)C2A—C21A—C26A—C25A−178.6 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1W0.882.032.901 (9)172
N1A—H1A···O1WA0.882.012.860 (9)163
O1W—H1W1···O1i0.841.992.832 (8)180
O1W—H1W2···O1Aii0.842.012.856 (8)180
O1WA—H1W3···O1iii0.842.062.897 (8)180
O1WA—H1W4···O1Aiv0.841.962.802 (7)180
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) x, −y+1, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1W0.882.032.901 (9)172
N1A—H1A···O1WA0.882.012.860 (9)163
O1W—H1W1···O1i0.841.992.832 (8)180
O1W—H1W2···O1Aii0.842.012.856 (8)180
O1WA—H1W3···O1iii0.842.062.897 (8)180
O1WA—H1W4···O1Aiv0.841.962.802 (7)180
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) x, −y+1, z+1/2.
Acknowledgements top

KS thanks the Department of Chemistry, Mangalore University for research facilities.

references
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