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Acta Cryst. (2008). E64, o2265    [ doi:10.1107/S1600536808035071 ]

2-Bromo-4-chloro-6-[(2,6-diisopropylphenyl)iminomethyl]phenol

K. K. Raja, I. M. Bilal, S. Thambidurai, G. Rajagopal and A. SubbiahPandi

Abstract top

There are two molecules in the asymmetric unit of the title compound, C19H21BrClNO, with dihedral angles between the aromatic rings of 70.0 (2) and 81.9 (3)°. The crystal structure is stabilized by intermolecular C-H...[pi] and C-Br...[pi] interactions. In additional, the stacked molecules exhibit intramolecular O-H...N hydrogen bonds.

Comment top

Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Pu, 2008). As a part of our ongoing investigation in this field we have determined the crystal structure of the title compound, (I).

Fig.1 shows the asymmetric unit consisting of two molecules of (I) viz. unit A and unit B. The two crystallographically independent molecules have the same geometrical parameters within the precision of the experiments. The bond lengths and angles in (I) are comparable to the corresponding values in the related structure, 2-Bezyliminomethyl-6-bromo-4-chloro-phenol (Pu, 2008). Like other Schiff base compounds containing salicylidene (Figuet et al., 2001; Kennedy & Reglinski, 2001; Thamotharan et al., 2003) the hydroxyl groups form intramolecular hydrogen bonds with the N atoms, thereby completing six-membered rings (Fig. 2). The molecular packing is stabilized by intermolecular C—H···π and C—Br···π interactions, with a C28—H28A···Cg1i separation of 2.96 Å and a C16—Br1···Cg2i separation of 3.532 (5) Å (Fig. 2 and Table 1; Cg1 and Cg2 are the centroids of the C14-C19 and C33-C38 benzene rings, respectively, symmetry code as in Fig. 2). In addition, the molecular packing is further stabilized by two intramolecular O—H···N hydrogen bonds (Table 1).

Related literature top

For the synthesis, see: Chang et al. (1998). For Schiff base compounds in coordination chemistry, see: Pu (2008). For Schiff base compounds containing salicylidene, see: Figuet et al. (2001); Kennedy & Reglinski (2001); Thamotharan et al. (2003). For related structures, see: Lin et al. (2005); Chen & Ye (2008). Cg1 is the centroid of the C14–C19 benzene ring.

Experimental top

The title compound was synthesized by refluxing an ethanol solution (20 ml) of 5-bromo-3-chloro-2-hydroxybenzaldehyde (1.72 g, 10 mmol) and 2,6-diisopropylaniline (1.72 g, 10 mmol), at 80°C for 2 h. Upon cooling to 0°C, a yellow solid crystalline product was obtained. The precipitate was filtered off and washed with cold ethanol. Single crystal of good diffraction quality was obtained by the recrystallization of compound with ethanol solution by slow evaporation method.

Refinement top

All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C—H distances fixed in the range (0.82–0.97)Å with Uiso(H)= 1.5Ueq(methyl H) and 1.2Ueq(for other H atoms).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004) and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, (1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. C—H···π, C—Br···π and O—H···N interactions (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry code: (i) -x+1, -y+1, -z+1.]
2-Bromo-4-chloro-6-[(2,6-diisopropylphenyl)iminomethyl]phenol top
Crystal data top
C19H21BrClNOF(000) = 1616
Mr = 394.73Dx = 1.355 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9432 reflections
a = 11.356 (2) Åθ = 1.6–28.1°
b = 15.045 (3) ŵ = 2.27 mm−1
c = 22.660 (5) ÅT = 293 K
β = 91.36 (3)°Block, colourless
V = 3870.4 (13) Å30.26 × 0.15 × 0.15 mm
Z = 8
Data collection top
Bruker APEXII CCD area-detector
diffractometer		6820 independent reflections
Radiation source: fine-focus sealed tube4111 reflections with I > 2σ(I)
graphiteRint = 0.045
Detector resolution: 10.0 pixels mm-1θmax = 25.0°, θmin = 1.6°
ω and φ scansh = −13→13
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −17→17
Tmin = 0.672, Tmax = 0.712l = −26→26
36408 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0678P)2 + 2.2687P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
6820 reflectionsΔρmax = 0.45 e Å−3
424 parametersΔρmin = −0.60 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0011 (2)
Crystal data top
C19H21BrClNOV = 3870.4 (13) Å3
Mr = 394.73Z = 8
Monoclinic, P21/nMo Kα radiation
a = 11.356 (2) ŵ = 2.27 mm−1
b = 15.045 (3) ÅT = 293 K
c = 22.660 (5) Å0.26 × 0.15 × 0.15 mm
β = 91.36 (3)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		6820 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4111 reflections with I > 2σ(I)
Tmin = 0.672, Tmax = 0.712Rint = 0.045
36408 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.146Δρmax = 0.45 e Å−3
S = 1.04Δρmin = −0.60 e Å−3
6820 reflectionsAbsolute structure: ?
424 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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 and torsion 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 > 2sigma(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
Br10.40344 (6)0.77524 (4)0.52632 (2)0.0958 (2)
Br20.84887 (5)−0.02832 (4)0.51695 (3)0.0954 (2)
Cl1−0.06647 (12)0.75082 (9)0.58127 (6)0.0945 (5)
Cl20.39884 (10)0.00891 (9)0.60014 (6)0.0805 (4)
O10.4129 (2)0.60711 (19)0.59597 (13)0.0682 (8)
H1A0.41470.56090.61520.102*
O20.8822 (2)0.14048 (19)0.58425 (13)0.0672 (8)
H2A0.89050.18750.60220.101*
N10.3289 (3)0.4748 (2)0.65542 (13)0.0535 (8)
N20.8189 (3)0.2768 (2)0.64732 (14)0.0564 (8)
C10.3129 (4)0.2336 (3)0.68334 (19)0.0645 (11)
H10.28330.18200.66600.077*
C20.3718 (4)0.2290 (3)0.7371 (2)0.0744 (13)
H20.37990.17450.75610.089*
C30.4184 (4)0.3039 (3)0.76285 (19)0.0748 (13)
H30.46000.29910.79860.090*
C40.4050 (4)0.3865 (3)0.73692 (17)0.0624 (11)
C50.3417 (3)0.3900 (3)0.68311 (16)0.0499 (9)
C60.2973 (3)0.3146 (3)0.65476 (16)0.0512 (9)
C70.2381 (4)0.3171 (3)0.59384 (19)0.0658 (11)
H70.23280.37970.58210.079*
C80.3125 (5)0.2709 (5)0.5489 (2)0.118 (2)
H8A0.31850.20890.55850.178*
H8B0.38970.29690.54930.178*
H8C0.27660.27760.51040.178*
C90.1148 (5)0.2808 (6)0.5929 (3)0.145 (3)
H9A0.11710.21790.59970.218*
H9B0.07790.29250.55510.218*
H9C0.07050.30900.62320.218*
C100.4545 (5)0.4695 (3)0.7655 (2)0.0890 (16)
H100.44940.51730.73630.107*
C110.3828 (7)0.4963 (6)0.8163 (4)0.205 (5)
H11A0.30290.50620.80320.307*
H11B0.41420.55000.83330.307*
H11C0.38470.45000.84550.307*
C120.5830 (6)0.4609 (5)0.7853 (3)0.136 (3)
H12A0.61640.51900.79060.204*
H12B0.62560.42930.75590.204*
H12C0.58790.42890.82200.204*
C130.2279 (4)0.5113 (3)0.65150 (15)0.0518 (10)
H130.16420.48360.66880.062*
C140.2094 (3)0.5947 (2)0.62079 (15)0.0494 (9)
C150.3027 (4)0.6388 (2)0.59373 (16)0.0522 (10)
C160.2787 (4)0.7172 (3)0.56345 (17)0.0627 (11)
C170.1650 (5)0.7516 (3)0.55948 (18)0.0703 (13)
H170.15000.80440.53930.084*
C180.0757 (4)0.7064 (3)0.58573 (19)0.0657 (12)
C190.0958 (4)0.6301 (3)0.61582 (17)0.0579 (10)
H190.03360.60100.63340.070*
C200.8777 (5)0.5253 (3)0.7251 (2)0.0784 (14)
H200.88850.58040.74300.094*
C210.9117 (4)0.4493 (4)0.7540 (2)0.0772 (14)
H210.94760.45400.79120.093*
C220.8946 (4)0.3656 (3)0.72966 (18)0.0672 (12)
C230.8386 (3)0.3623 (3)0.67371 (17)0.0538 (10)
C240.8085 (3)0.4385 (3)0.64220 (17)0.0542 (10)
C250.8273 (4)0.5199 (3)0.66907 (18)0.0664 (12)
H250.80570.57170.64920.080*
C260.7578 (4)0.4342 (3)0.57945 (18)0.0682 (12)
H260.76220.37200.56680.082*
C270.6302 (5)0.4608 (5)0.5760 (3)0.135 (3)
H27A0.58760.42910.60550.202*
H27B0.59800.44670.53760.202*
H27C0.62350.52350.58280.202*
C280.8313 (7)0.4877 (5)0.5378 (2)0.123 (2)
H28A0.81030.47230.49780.185*
H28B0.91320.47500.54510.185*
H28C0.81720.54990.54390.185*
C290.9318 (5)0.2826 (4)0.7619 (2)0.0933 (17)
H290.92850.23360.73340.112*
C300.8473 (7)0.2609 (6)0.8100 (4)0.168 (4)
H30A0.84820.30800.83860.253*
H30B0.87070.20630.82880.253*
H30C0.76930.25460.79330.253*
C311.0574 (6)0.2868 (5)0.7873 (3)0.129 (2)
H31A1.06120.32930.81880.193*
H31B1.11010.30430.75690.193*
H31C1.08000.22930.80210.193*
C320.7163 (4)0.2424 (3)0.64959 (16)0.0545 (10)
H320.65810.27260.66960.065*
C330.6875 (3)0.1580 (3)0.62199 (15)0.0487 (9)
C340.7715 (3)0.1114 (3)0.58969 (17)0.0523 (10)
C350.7374 (4)0.0327 (3)0.56155 (18)0.0582 (10)
C360.6244 (4)0.0016 (3)0.56471 (18)0.0599 (11)
H360.6026−0.05080.54560.072*
C370.5435 (4)0.0485 (3)0.59632 (17)0.0577 (11)
C380.5731 (3)0.1258 (3)0.62503 (16)0.0535 (10)
H380.51710.15640.64640.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1269 (5)0.0750 (4)0.0857 (4)−0.0169 (3)0.0053 (3)0.0256 (3)
Br20.0774 (4)0.0823 (4)0.1261 (5)0.0228 (3)−0.0081 (3)−0.0355 (3)
Cl10.0945 (9)0.0948 (10)0.0926 (9)0.0458 (8)−0.0318 (7)−0.0111 (7)
Cl20.0632 (7)0.0844 (8)0.0938 (9)−0.0237 (6)−0.0056 (6)0.0003 (7)
O10.0665 (18)0.0584 (18)0.080 (2)0.0030 (14)0.0035 (15)0.0180 (15)
O20.0524 (17)0.0645 (19)0.084 (2)−0.0023 (14)−0.0048 (14)−0.0114 (15)
N10.058 (2)0.049 (2)0.0534 (19)0.0039 (16)−0.0065 (15)0.0063 (15)
N20.059 (2)0.055 (2)0.055 (2)−0.0039 (16)−0.0047 (16)−0.0025 (16)
C10.071 (3)0.052 (3)0.071 (3)0.000 (2)0.011 (2)0.009 (2)
C20.092 (3)0.065 (3)0.067 (3)0.017 (3)0.011 (3)0.025 (3)
C30.093 (3)0.079 (4)0.053 (3)0.015 (3)−0.008 (2)0.018 (3)
C40.073 (3)0.065 (3)0.048 (2)0.008 (2)−0.007 (2)0.007 (2)
C50.050 (2)0.048 (2)0.051 (2)0.0043 (18)0.0009 (17)0.0100 (19)
C60.050 (2)0.054 (2)0.050 (2)0.0012 (18)0.0025 (17)0.006 (2)
C70.070 (3)0.058 (3)0.069 (3)0.002 (2)−0.009 (2)−0.004 (2)
C80.102 (4)0.190 (7)0.064 (3)0.030 (4)0.000 (3)−0.010 (4)
C90.068 (4)0.263 (10)0.104 (5)−0.039 (5)−0.011 (3)−0.006 (5)
C100.109 (4)0.084 (4)0.072 (3)0.007 (3)−0.039 (3)−0.003 (3)
C110.127 (6)0.229 (10)0.262 (11)−0.018 (6)0.058 (7)−0.171 (9)
C120.104 (5)0.158 (7)0.146 (6)−0.026 (4)0.000 (4)−0.046 (5)
C130.062 (3)0.053 (2)0.041 (2)0.000 (2)0.0007 (18)0.0027 (18)
C140.065 (2)0.045 (2)0.038 (2)0.0080 (19)−0.0076 (18)−0.0048 (17)
C150.072 (3)0.043 (2)0.041 (2)0.003 (2)−0.0069 (19)−0.0025 (18)
C160.094 (3)0.050 (3)0.044 (2)−0.001 (2)−0.007 (2)0.001 (2)
C170.109 (4)0.049 (3)0.052 (3)0.018 (3)−0.023 (3)0.000 (2)
C180.083 (3)0.059 (3)0.054 (3)0.023 (2)−0.022 (2)−0.007 (2)
C190.062 (2)0.062 (3)0.049 (2)0.012 (2)−0.0101 (19)−0.008 (2)
C200.097 (4)0.075 (3)0.063 (3)−0.025 (3)0.005 (3)−0.022 (3)
C210.094 (3)0.087 (4)0.050 (3)−0.013 (3)−0.009 (2)−0.013 (3)
C220.077 (3)0.072 (3)0.052 (3)−0.008 (2)−0.004 (2)−0.007 (2)
C230.053 (2)0.057 (3)0.052 (2)−0.0062 (19)0.0045 (19)−0.011 (2)
C240.057 (2)0.056 (3)0.049 (2)−0.0057 (19)0.0018 (18)−0.009 (2)
C250.080 (3)0.059 (3)0.060 (3)−0.007 (2)0.007 (2)−0.007 (2)
C260.086 (3)0.060 (3)0.058 (3)0.002 (2)−0.014 (2)−0.009 (2)
C270.100 (5)0.185 (8)0.117 (5)0.036 (5)−0.044 (4)−0.016 (5)
C280.183 (6)0.135 (5)0.051 (3)−0.051 (5)−0.004 (3)0.000 (3)
C290.125 (5)0.091 (4)0.062 (3)−0.005 (3)−0.023 (3)0.004 (3)
C300.131 (6)0.188 (8)0.186 (8)−0.012 (6)0.008 (6)0.109 (7)
C310.123 (5)0.164 (7)0.099 (5)0.027 (5)−0.016 (4)0.031 (4)
C320.057 (3)0.061 (3)0.045 (2)0.002 (2)−0.0028 (18)0.0005 (19)
C330.053 (2)0.052 (2)0.040 (2)−0.0047 (18)−0.0110 (17)0.0057 (18)
C340.050 (2)0.051 (2)0.055 (2)0.0019 (19)−0.0112 (18)0.007 (2)
C350.062 (3)0.048 (2)0.064 (3)0.011 (2)−0.015 (2)0.001 (2)
C360.070 (3)0.046 (2)0.063 (3)0.002 (2)−0.017 (2)0.007 (2)
C370.059 (2)0.062 (3)0.051 (2)−0.011 (2)−0.011 (2)0.013 (2)
C380.056 (2)0.057 (3)0.047 (2)−0.0009 (19)−0.0038 (18)0.0064 (19)
Geometric parameters (Å, °) top
Br1—C161.880 (5)C15—C161.388 (5)
Br2—C351.878 (4)C16—C171.392 (6)
Cl1—C181.748 (5)C17—C181.369 (6)
Cl2—C371.751 (4)C17—H170.9300
O1—C151.339 (5)C18—C191.351 (6)
O1—H1A0.8200C19—H190.9300
O2—C341.339 (4)C20—C211.368 (7)
O2—H2A0.8200C20—C251.382 (6)
N1—C131.273 (5)C20—H200.9300
N1—C51.427 (5)C21—C221.387 (6)
N2—C321.276 (5)C21—H210.9300
N2—C231.434 (5)C22—C231.406 (5)
C1—C21.377 (6)C22—C291.503 (7)
C1—C61.389 (5)C23—C241.390 (5)
C1—H10.9300C24—C251.381 (6)
C2—C31.370 (7)C24—C261.523 (5)
C2—H20.9300C25—H250.9300
C3—C41.380 (6)C26—C271.504 (7)
C3—H30.9300C26—C281.507 (7)
C4—C51.402 (5)C26—H260.9800
C4—C101.510 (6)C27—H27A0.9600
C5—C61.393 (5)C27—H27B0.9600
C6—C71.521 (5)C27—H27C0.9600
C7—C91.503 (7)C28—H28A0.9600
C7—C81.507 (7)C28—H28B0.9600
C7—H70.9800C28—H28C0.9600
C8—H8A0.9600C29—C301.505 (8)
C8—H8B0.9600C29—C311.527 (8)
C8—H8C0.9600C29—H290.9800
C9—H9A0.9600C30—H30A0.9600
C9—H9B0.9600C30—H30B0.9600
C9—H9C0.9600C30—H30C0.9600
C10—C111.482 (8)C31—H31A0.9600
C10—C121.522 (8)C31—H31B0.9600
C10—H100.9800C31—H31C0.9600
C11—H11A0.9600C32—C331.450 (5)
C11—H11B0.9600C32—H320.9300
C11—H11C0.9600C33—C381.390 (5)
C12—H12A0.9600C33—C341.404 (5)
C12—H12B0.9600C34—C351.395 (5)
C12—H12C0.9600C35—C361.371 (6)
C13—C141.448 (5)C36—C371.373 (6)
C13—H130.9300C36—H360.9300
C14—C191.398 (5)C37—C381.370 (5)
C14—C151.403 (5)C38—H380.9300
C15—O1—H1A109.5C18—C19—H19119.7
C34—O2—H2A109.5C14—C19—H19119.7
C13—N1—C5119.9 (3)C21—C20—C25119.7 (4)
C32—N2—C23118.7 (3)C21—C20—H20120.1
C2—C1—C6120.7 (4)C25—C20—H20120.1
C2—C1—H1119.7C20—C21—C22122.2 (4)
C6—C1—H1119.7C20—C21—H21118.9
C3—C2—C1120.7 (4)C22—C21—H21118.9
C3—C2—H2119.7C21—C22—C23116.5 (4)
C1—C2—H2119.7C21—C22—C29121.8 (4)
C2—C3—C4121.4 (4)C23—C22—C29121.6 (4)
C2—C3—H3119.3C24—C23—C22122.3 (4)
C4—C3—H3119.3C24—C23—N2119.5 (3)
C3—C4—C5117.0 (4)C22—C23—N2118.1 (4)
C3—C4—C10121.7 (4)C25—C24—C23118.1 (4)
C5—C4—C10121.3 (4)C25—C24—C26120.0 (4)
C6—C5—C4122.8 (4)C23—C24—C26121.8 (4)
C6—C5—N1119.6 (3)C24—C25—C20120.9 (4)
C4—C5—N1117.5 (4)C24—C25—H25119.6
C1—C6—C5117.3 (4)C20—C25—H25119.6
C1—C6—C7119.6 (4)C27—C26—C28111.9 (5)
C5—C6—C7123.0 (4)C27—C26—C24112.3 (4)
C9—C7—C8111.1 (5)C28—C26—C24111.1 (4)
C9—C7—C6113.3 (4)C27—C26—H26107.1
C8—C7—C6111.0 (4)C28—C26—H26107.1
C9—C7—H7107.0C24—C26—H26107.1
C8—C7—H7107.0C26—C27—H27A109.5
C6—C7—H7107.0C26—C27—H27B109.5
C7—C8—H8A109.5H27A—C27—H27B109.5
C7—C8—H8B109.5C26—C27—H27C109.5
H8A—C8—H8B109.5H27A—C27—H27C109.5
C7—C8—H8C109.5H27B—C27—H27C109.5
H8A—C8—H8C109.5C26—C28—H28A109.5
H8B—C8—H8C109.5C26—C28—H28B109.5
C7—C9—H9A109.5H28A—C28—H28B109.5
C7—C9—H9B109.5C26—C28—H28C109.5
H9A—C9—H9B109.5H28A—C28—H28C109.5
C7—C9—H9C109.5H28B—C28—H28C109.5
H9A—C9—H9C109.5C22—C29—C30110.8 (5)
H9B—C9—H9C109.5C22—C29—C31113.4 (5)
C11—C10—C4110.7 (5)C30—C29—C31110.0 (5)
C11—C10—C12109.6 (5)C22—C29—H29107.4
C4—C10—C12113.6 (5)C30—C29—H29107.4
C11—C10—H10107.6C31—C29—H29107.4
C4—C10—H10107.6C29—C30—H30A109.5
C12—C10—H10107.6C29—C30—H30B109.5
C10—C11—H11A109.5H30A—C30—H30B109.5
C10—C11—H11B109.5C29—C30—H30C109.5
H11A—C11—H11B109.5H30A—C30—H30C109.5
C10—C11—H11C109.5H30B—C30—H30C109.5
H11A—C11—H11C109.5C29—C31—H31A109.5
H11B—C11—H11C109.5C29—C31—H31B109.5
C10—C12—H12A109.5H31A—C31—H31B109.5
C10—C12—H12B109.5C29—C31—H31C109.5
H12A—C12—H12B109.5H31A—C31—H31C109.5
C10—C12—H12C109.5H31B—C31—H31C109.5
H12A—C12—H12C109.5N2—C32—C33122.3 (4)
H12B—C12—H12C109.5N2—C32—H32118.8
N1—C13—C14121.9 (4)C33—C32—H32118.8
N1—C13—H13119.1C38—C33—C34120.0 (4)
C14—C13—H13119.1C38—C33—C32119.1 (4)
C19—C14—C15119.3 (4)C34—C33—C32120.8 (3)
C19—C14—C13119.5 (4)O2—C34—C35119.1 (4)
C15—C14—C13121.2 (3)O2—C34—C33122.4 (3)
O1—C15—C16119.5 (4)C35—C34—C33118.5 (4)
O1—C15—C14122.0 (3)C36—C35—C34121.1 (4)
C16—C15—C14118.5 (4)C36—C35—Br2120.3 (3)
C15—C16—C17121.2 (4)C34—C35—Br2118.5 (3)
C15—C16—Br1118.4 (3)C35—C36—C37119.4 (4)
C17—C16—Br1120.4 (3)C35—C36—H36120.3
C18—C17—C16118.8 (4)C37—C36—H36120.3
C18—C17—H17120.6C38—C37—C36121.6 (4)
C16—C17—H17120.6C38—C37—Cl2119.0 (3)
C19—C18—C17121.6 (4)C36—C37—Cl2119.4 (3)
C19—C18—Cl1119.9 (4)C37—C38—C33119.4 (4)
C17—C18—Cl1118.5 (3)C37—C38—H38120.3
C18—C19—C14120.6 (4)C33—C38—H38120.3
C6—C1—C2—C3−1.5 (7)C25—C20—C21—C22−1.8 (8)
C1—C2—C3—C42.1 (7)C20—C21—C22—C23−0.9 (7)
C2—C3—C4—C5−0.1 (7)C20—C21—C22—C29−179.7 (5)
C2—C3—C4—C10179.0 (5)C21—C22—C23—C244.1 (6)
C3—C4—C5—C6−2.6 (6)C29—C22—C23—C24−177.0 (4)
C10—C4—C5—C6178.4 (4)C21—C22—C23—N2−179.7 (4)
C3—C4—C5—N1−179.0 (4)C29—C22—C23—N2−0.9 (6)
C10—C4—C5—N12.0 (6)C32—N2—C23—C24−82.8 (5)
C13—N1—C5—C671.3 (5)C32—N2—C23—C22100.9 (4)
C13—N1—C5—C4−112.2 (4)C22—C23—C24—C25−4.6 (6)
C2—C1—C6—C5−1.0 (6)N2—C23—C24—C25179.3 (3)
C2—C1—C6—C7176.6 (4)C22—C23—C24—C26174.5 (4)
C4—C5—C6—C13.1 (6)N2—C23—C24—C26−1.7 (6)
N1—C5—C6—C1179.4 (3)C23—C24—C25—C201.8 (6)
C4—C5—C6—C7−174.4 (4)C26—C24—C25—C20−177.3 (4)
N1—C5—C6—C72.0 (6)C21—C20—C25—C241.3 (7)
C1—C6—C7—C960.1 (6)C25—C24—C26—C27−70.8 (6)
C5—C6—C7—C9−122.5 (5)C23—C24—C26—C27110.2 (5)
C1—C6—C7—C8−65.7 (6)C25—C24—C26—C2855.4 (6)
C5—C6—C7—C8111.7 (5)C23—C24—C26—C28−123.7 (5)
C3—C4—C10—C11−74.4 (7)C21—C22—C29—C3075.9 (7)
C5—C4—C10—C11104.6 (6)C23—C22—C29—C30−102.9 (6)
C3—C4—C10—C1249.4 (7)C21—C22—C29—C31−48.4 (7)
C5—C4—C10—C12−131.6 (5)C23—C22—C29—C31132.9 (5)
C5—N1—C13—C14−176.3 (3)C23—N2—C32—C33177.4 (3)
N1—C13—C14—C19177.5 (4)N2—C32—C33—C38−178.4 (4)
N1—C13—C14—C150.3 (5)N2—C32—C33—C34−2.0 (6)
C19—C14—C15—O1−178.6 (3)C38—C33—C34—O2178.5 (3)
C13—C14—C15—O1−1.4 (5)C32—C33—C34—O22.2 (5)
C19—C14—C15—C160.8 (5)C38—C33—C34—C35−0.5 (5)
C13—C14—C15—C16178.1 (3)C32—C33—C34—C35−176.8 (3)
O1—C15—C16—C17179.2 (4)O2—C34—C35—C36−178.4 (4)
C14—C15—C16—C17−0.3 (6)C33—C34—C35—C360.6 (6)
O1—C15—C16—Br10.3 (5)O2—C34—C35—Br2−0.3 (5)
C14—C15—C16—Br1−179.2 (3)C33—C34—C35—Br2178.7 (3)
C15—C16—C17—C18−0.5 (6)C34—C35—C36—C37−0.3 (6)
Br1—C16—C17—C18178.3 (3)Br2—C35—C36—C37−178.3 (3)
C16—C17—C18—C190.8 (6)C35—C36—C37—C38−0.2 (6)
C16—C17—C18—Cl1179.3 (3)C35—C36—C37—Cl2179.8 (3)
C17—C18—C19—C14−0.3 (6)C36—C37—C38—C330.3 (6)
Cl1—C18—C19—C14−178.7 (3)Cl2—C37—C38—C33−179.6 (3)
C15—C14—C19—C18−0.5 (6)C34—C33—C38—C370.0 (5)
C13—C14—C19—C18−177.8 (3)C32—C33—C38—C37176.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.872.598 (4)147
O2—H2A···N20.821.882.610 (4)147
C28—H28A···Cg1i0.962.963.773 (6)144
C16—Br1···Cg4i1.8803.534.75 (2)120
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.872.598 (4)147
O2—H2A···N20.821.882.610 (4)147
C28—H28A···Cg1i0.962.963.773 (6)144
C16—Br1···Cg4i1.8803.534.75 (2)120
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

The authors are grateful to Mr J. Jothi Kumar, Principal of Presidency College (Autonomous), Chennai, for providing the necessary facilities. Dr Babu Varghese, SAIF, IIT, Madras, India, is thanked for collecting the X-ray intensity data.

references
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