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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 10| October 2008| Pages o1895-o1896

N,N′-Bis(5-bromo-2-hy­droxy­benzyl­­idene)-2,2-di­methylpropane-1,3-di­amine

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
*Correspondence e-mail: hkfun@usm.my

(Received 2 September 2008; accepted 3 September 2008; online 6 September 2008)

The crystal structure of the title Schiff base compound, C19H20Br2N2O2, contains two crystallographically independent mol­ecules (A and B) in the asymmetric unit, with similar conformations. Intra­molecular O—H⋯N (× 4) and C—H⋯N (× 5) hydrogen bonds form six- and five-membered rings, producing S(6) and S(5) ring motifs, respectively. One of the N atoms in mol­ecule A acts as a trifurcated acceptor, the rest of the N atoms being bifurcated acceptors. The dihedral angles between the benzene rings in mol­ecules A and B are 47.83 (17) and 61.11 (17)°, respectively. The mol­ecular conformation is stabilized by intra­molecular O—H⋯N and C—H⋯N hydrogen bonds. The short distances between the centroids of the benzene rings [3.7799 (19)–3.890 (2) Å] indicate the existence of ππ inter­actions. In addition, the crystal structure is further stabilized by an inter­molecular C—H⋯O hydrogen bond, C—H⋯π inter­actions, and short inter­molecular Br⋯Br and Br⋯O contacts [3.4786 (5) and 3.149 (3) Å, respectively].

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For information on Schiff base ligands and complexes and their applications, see, for example: Fun, Kargar & Kia (2008[Fun, H.-K., Kargar, H. & Kia, R. (2008). Acta Cryst. E64, o1308.]); Fun, Kia & Kargar (2008[Fun, H.-K., Kia, R. & Kargar, H. (2008). Acta Cryst. E64, o1335.]); Fun, Mirkhani et al. (2008a[Fun, H.-K., Mirkhani, V., Kia, R. & Vartooni, A. R. (2008a). Acta Cryst. E64, o1374-o1375.],b[Fun, H.-K., Mirkhani, V., Kia, R. & Vartooni, A. R. (2008b). Acta Cryst. E64, o1471.]); Calligaris & Randaccio (1987[Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, edited by G. Wilkinson, pp. 715-738. London: Pergamon.]); Casellato & Vigato (1977[Casellato, U. & Vigato, P. A. (1977). Coord. Chem. Rev. 23, 31-50.]); Pal et al. (2005[Pal, S., Barik, A. K., Gupta, S., Hazra, A., Kar, S. K., Peng, S.-M., Lee, G.-H., Butcher, R. J., El Fallah, M. S. & Ribas, J. (2005). Inorg. Chem. 44, 3880-3889.]); Reglinski et al. 2004[Reglinski, J., Taylor, M. K. & Kennedy, A. R. (2004). Acta Cryst. C60, o169-o172.]; Hou et al. (2001[Hou, B., Friedman, N., Ruhman, S., Sheves, M. & Ottolenghi, M. (2001). J. Phys. Chem. B, 105, 7042-7048.]); Ren et al. (2002[Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410-419.]).

[Scheme 1]

Experimental

Crystal data
  • C19H20Br2N2O2

  • Mr = 468.19

  • Monoclinic, C 2/c

  • a = 31.7684 (10) Å

  • b = 6.2436 (2) Å

  • c = 38.7287 (11) Å

  • β = 99.870 (2)°

  • V = 7568.1 (4) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 4.30 mm−1

  • T = 100.0 (1) K

  • 0.52 × 0.10 × 0.06 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.213, Tmax = 0.782

  • 47391 measured reflections

  • 11172 independent reflections

  • 6920 reflections with I > 2σ(I)

  • Rint = 0.080

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.110

  • S = 1.01

  • 11172 reflections

  • 463 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.57 e Å−3

  • Δρmin = −0.46 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1B—H1OB⋯N1B 0.85 1.81 2.580 (4) 151
O2A—H2OA⋯N2A 0.85 (4) 1.79 (4) 2.578 (4) 154 (4)
O1A—H1OA⋯N1A 0.79 (5) 1.85 (5) 2.572 (4) 153 (4)
O2B—H2OB⋯N2B 0.73 (5) 1.94 (5) 2.586 (4) 149 (5)
C8A—H8AA⋯N2A 0.99 2.58 2.960 (4) 103
C8B—H8BA⋯N2B 0.99 2.60 2.966 (4) 102
C16B—H16B⋯O2Bi 0.95 2.58 3.290 (5) 131
C19A—H19B⋯N1A 0.98 2.58 2.918 (4) 100
C19A—H19C⋯N2A 0.98 2.58 2.933 (5) 101
C19B—H19F⋯N1B 0.98 2.60 2.926 (5) 100
C7B—H7BACg1ii 0.95 2.96 3.571 (4) 123
C18B—H18DCg2iii 0.98 2.77 3.652 (4) 151
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y-1, z; (iii) [x, -y-1, z-{\script{1\over 2}}]. Cg1 and Cg2 are the centroids of the C1A–C6A and C12A–C17A benzene rings, respectively.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

The condensation of primary amines with carbonyl compounds yields Schiff base (Casellato & Vigato, 1977) that are still now regarded as one of the most potential group of chelators for facile preparations of metallo-organic hybrid materials. In the past two decades, the synthesis, structure and properties of Schiff base complexes have stimulated much interest for their noteworthy contributions in single molecule-based magnetism, materials science, catalysis of many reactions like carbonylation, hydroformylation, reduction, oxidation, epoxidation and hydrolysis, etc. (Pal et al., 2005; Reglinski et al., 2004; Hou et al., 2001; Ren et al., 2002). Only a relatively small number of free Schiff base ligands have been characterized by X-ray crystallography (Calligaris & Randaccio, 1987). As an extension of our work (Fun, Kargar & Kia, 2008; Fun, Kia & Kargar, 2008; Fun, Mirkhani et al., 2008a,b) on the structural characterization of Schiff base compounds, the title compound (I), is reported here.

The crystal structure of the title compound (I) (Fig. I), contains two crystallographically independent molecules (A and B) in the asymmetric unit, with similar conformations. The bond lengths and angles are within normal ranges (Allen et al., 1987). Intramolecular O—H···N (x 4) and C—H···N (x 5) hydrogen bonds form six- and five-membered rings, producing S(6) and S(5) ring motifs, respectively (Bernstein et al. 1995) (Table 1). One of the nitrogen atoms in the molecule A acts as a trifurcated acceptor, but the rest of the nitrogen atoms are bifurcated acceptors. The dihedral angles between the benzene rings in molecule A and B is 47.83 (17)° and 61.11 (17)°. The molecular conformation is stabilized by intramolecular O—H···N and C—H···N hydrogen bonds. The short distances between the centroids of the benzene rings [Cg2–Cg2 = 3.7799 (19) Å and Cg3–Cg3 = 3.890 (2) Å] indicate the existence of ππ interactions. The Cg2 and Cg3 are the centroids of the C12A–C17A and C12B–C17B benzene rings. The interesting features of the crystal structure are short intermolecular Br···Br [symmetry code: 1/2 + x, -1/2 - y + 1/2 + z] and Br···O [symmetry code: -x, 1 + y, 1/2 - z] interactions, with distances of 3.4786 (5) and 3.149 (3) Å, respectively, which are significantly shorter than the sum of the van der Waals radii of the relevent atoms.

In addition, the crystal structure is further stabilized by intermolecular C—H···O hydrogen bond and C—H···π interactions.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For information on Schiff base ligands and complexes and their applications, see, for example: Fun, Kargar & Kia (2008); Fun, Kia & Kargar (2008); Fun, Mirkhani et al. (2008a,b); Calligaris & Randaccio (1987); Casellato & Vigato (1977); Pal et al. (2005); Reglinski et al. 2004; Hou et al. (2001); Ren et al. (2002).

Experimental top

The synthetic method has been described earlier (Reglinski et al., 2004). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution at room temperature.

Refinement top

H atoms bound to the O1A, O2A, and O2B were located in a difference Fourier map and refined freely. H atom bound to O1B was located from a difference Fourier map and constrained to refine with the parent atom after distance restraint of 0.84 (1) Å. The rest of the H atoms were positioned geometrically (C—H = 0.95–0.99 Å) and refined using a riding model.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability ellipsoids for non-H atoms. Intramolecular interactions are shown as dashed lines.
[Figure 2] Fig. 2. The crystal packing of (I), showing stacking of molecules down the b-axis. Intramolecular and intermolecular interactions are shown as dashed lines.
N,N'-Bis(5-bromo-2-hydroxybenzylidene)-2,2-dimethylpropane- 1,3-diamine top
Crystal data top
C19H20Br2N2O2F(000) = 3744
Mr = 468.19Dx = 1.644 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5640 reflections
a = 31.7684 (10) Åθ = 3.0–27.0°
b = 6.2436 (2) ŵ = 4.30 mm1
c = 38.7287 (11) ÅT = 100 K
β = 99.870 (2)°Needle, yellow
V = 7568.1 (4) Å30.52 × 0.10 × 0.06 mm
Z = 16
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
11172 independent reflections
Radiation source: fine-focus sealed tube6920 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
ϕ and ω scansθmax = 30.2°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 3644
Tmin = 0.213, Tmax = 0.783k = 88
47391 measured reflectionsl = 5454
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0443P)2 + 4.1476P]
where P = (Fo2 + 2Fc2)/3
11172 reflections(Δ/σ)max = 0.001
463 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.46 e Å3
Crystal data top
C19H20Br2N2O2V = 7568.1 (4) Å3
Mr = 468.19Z = 16
Monoclinic, C2/cMo Kα radiation
a = 31.7684 (10) ŵ = 4.30 mm1
b = 6.2436 (2) ÅT = 100 K
c = 38.7287 (11) Å0.52 × 0.10 × 0.06 mm
β = 99.870 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
11172 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
6920 reflections with I > 2σ(I)
Tmin = 0.213, Tmax = 0.783Rint = 0.080
47391 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.57 e Å3
11172 reflectionsΔρmin = 0.46 e Å3
463 parameters
Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br1A0.048763 (12)0.47249 (7)0.124135 (9)0.02437 (10)
Br2A0.330044 (11)0.00679 (6)0.479516 (9)0.02179 (9)
O1A0.06595 (9)0.8408 (5)0.26946 (7)0.0269 (6)
O2A0.18364 (8)0.6081 (4)0.43058 (7)0.0214 (6)
N1A0.09915 (9)0.4834 (5)0.29342 (7)0.0207 (7)
N2A0.14171 (9)0.2889 (5)0.39950 (7)0.0185 (6)
C1A0.06195 (11)0.7509 (6)0.23744 (9)0.0197 (8)
C2A0.04274 (11)0.8701 (6)0.20872 (10)0.0231 (8)
H2AA0.03211.00930.21210.028*
C3A0.03900 (11)0.7879 (6)0.17532 (9)0.0206 (8)
H3AA0.02610.87090.15580.025*
C4A0.05410 (11)0.5838 (6)0.17031 (9)0.0202 (8)
C5A0.07244 (11)0.4615 (6)0.19833 (9)0.0191 (8)
H5AA0.08250.32150.19460.023*
C6A0.07639 (11)0.5435 (6)0.23258 (9)0.0182 (8)
C7A0.09411 (11)0.4094 (6)0.26223 (9)0.0197 (8)
H7AA0.10200.26570.25840.024*
C8A0.11469 (11)0.3431 (6)0.32298 (9)0.0200 (8)
H8AA0.14260.39590.33530.024*
H8AB0.11890.19690.31430.024*
C9A0.08291 (11)0.3352 (6)0.34871 (9)0.0178 (7)
C10A0.10260 (11)0.1953 (6)0.37987 (9)0.0191 (8)
H10A0.08160.17650.39580.023*
H10B0.10910.05200.37120.023*
C11A0.17384 (11)0.1677 (6)0.40944 (8)0.0182 (8)
H11A0.17240.02070.40300.022*
C12A0.21289 (11)0.2529 (6)0.43068 (8)0.0168 (7)
C13A0.24770 (11)0.1167 (6)0.44173 (8)0.0174 (7)
H13A0.24670.02790.43400.021*
C14A0.28333 (10)0.1924 (6)0.46376 (9)0.0166 (7)
C15A0.28534 (11)0.4037 (6)0.47528 (8)0.0187 (8)
H15A0.30970.45400.49090.022*
C16A0.25179 (11)0.5388 (6)0.46392 (9)0.0191 (8)
H16A0.25340.68360.47150.023*
C17A0.21539 (11)0.4681 (6)0.44144 (9)0.0170 (7)
C18A0.04145 (11)0.2283 (7)0.33119 (10)0.0235 (8)
H18A0.02110.22540.34760.035*
H18B0.04750.08140.32450.035*
H18C0.02910.30940.31020.035*
C19A0.07370 (12)0.5588 (6)0.36131 (9)0.0222 (8)
H19A0.05320.54910.37750.033*
H19B0.06170.64760.34120.033*
H19C0.10030.62350.37340.033*
Br1B0.203156 (14)0.21813 (7)0.339930 (10)0.03229 (11)
Br2B0.107371 (12)0.17661 (7)0.040046 (10)0.02582 (10)
O1B0.18949 (9)0.3706 (4)0.21548 (7)0.0311 (7)
H1OB0.17330.30890.19880.047*
O2B0.04871 (9)0.3734 (5)0.04206 (7)0.0234 (6)
N1B0.15040 (9)0.0685 (5)0.17729 (7)0.0210 (7)
N2B0.09435 (9)0.0503 (5)0.06810 (7)0.0203 (7)
C1B0.19306 (11)0.2322 (6)0.24240 (10)0.0230 (8)
C2B0.21359 (12)0.2995 (7)0.27530 (10)0.0274 (9)
H2BA0.22550.43920.27810.033*
C3B0.21669 (12)0.1653 (7)0.30373 (10)0.0260 (9)
H3BA0.23060.21260.32610.031*
C4B0.19961 (12)0.0384 (7)0.29977 (9)0.0241 (9)
C5B0.17993 (11)0.1126 (6)0.26741 (9)0.0205 (8)
H5BA0.16870.25390.26500.025*
C6B0.17662 (11)0.0223 (6)0.23812 (9)0.0195 (8)
C7B0.15596 (11)0.0552 (6)0.20381 (9)0.0185 (8)
H7BA0.14660.19970.20120.022*
C8B0.13053 (11)0.0151 (6)0.14318 (9)0.0220 (8)
H8BA0.10220.05220.13600.026*
H8BB0.12630.17160.14490.026*
C9B0.15859 (11)0.0308 (6)0.11529 (9)0.0202 (8)
C10B0.13537 (11)0.0555 (7)0.08002 (9)0.0218 (8)
H10C0.15390.03550.06210.026*
H10D0.13050.21110.08220.026*
C11B0.06085 (11)0.0637 (6)0.06348 (9)0.0193 (8)
H11B0.06320.21350.06760.023*
C12B0.01870 (11)0.0298 (6)0.05198 (8)0.0175 (7)
C13B0.01786 (11)0.0943 (6)0.05134 (9)0.0203 (8)
H13B0.01540.23900.05900.024*
C14B0.05760 (11)0.0080 (6)0.03961 (9)0.0188 (8)
C15B0.06189 (11)0.2017 (6)0.02785 (9)0.0213 (8)
H15B0.08940.25900.01930.026*
C16B0.02609 (11)0.3268 (6)0.02854 (9)0.0212 (8)
H16B0.02900.47050.02040.025*
C17B0.01438 (11)0.2447 (6)0.04102 (9)0.0192 (8)
C18B0.20099 (11)0.0906 (7)0.12457 (10)0.0249 (9)
H18D0.21900.05980.10700.037*
H18E0.19530.24480.12500.037*
H18F0.21580.04470.14770.037*
C19B0.16738 (12)0.2702 (6)0.11289 (10)0.0239 (8)
H19D0.14020.34740.10690.036*
H19E0.18490.29550.09480.036*
H19F0.18270.32150.13550.036*
H2OA0.1637 (13)0.531 (7)0.4195 (10)0.027 (12)*
H1OA0.0731 (13)0.745 (8)0.2823 (11)0.031 (14)*
H2OB0.0676 (14)0.317 (8)0.0506 (12)0.043 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.02596 (19)0.0293 (2)0.01827 (17)0.00233 (18)0.00511 (14)0.00038 (16)
Br2A0.01765 (17)0.0224 (2)0.02391 (17)0.00251 (16)0.00050 (13)0.00215 (16)
O1A0.0358 (16)0.0207 (16)0.0234 (14)0.0043 (14)0.0028 (12)0.0006 (13)
O2A0.0205 (13)0.0148 (14)0.0271 (13)0.0027 (12)0.0014 (11)0.0022 (12)
N1A0.0187 (15)0.0206 (17)0.0223 (14)0.0010 (14)0.0022 (12)0.0022 (14)
N2A0.0204 (15)0.0166 (17)0.0176 (14)0.0015 (14)0.0008 (12)0.0022 (13)
C1A0.0174 (17)0.019 (2)0.0241 (18)0.0018 (16)0.0064 (14)0.0020 (16)
C2A0.0231 (19)0.017 (2)0.030 (2)0.0026 (17)0.0064 (16)0.0017 (17)
C3A0.0163 (17)0.021 (2)0.0241 (18)0.0019 (16)0.0028 (14)0.0081 (16)
C4A0.0179 (17)0.026 (2)0.0179 (16)0.0035 (17)0.0051 (14)0.0008 (16)
C5A0.0158 (16)0.017 (2)0.0247 (18)0.0005 (15)0.0050 (14)0.0001 (16)
C6A0.0155 (17)0.0166 (19)0.0224 (17)0.0002 (15)0.0033 (13)0.0023 (15)
C7A0.0177 (18)0.019 (2)0.0235 (18)0.0010 (16)0.0055 (14)0.0019 (16)
C8A0.0171 (17)0.022 (2)0.0195 (17)0.0012 (16)0.0009 (14)0.0003 (16)
C9A0.0184 (17)0.0150 (19)0.0192 (16)0.0017 (16)0.0008 (13)0.0016 (15)
C10A0.0166 (17)0.018 (2)0.0226 (17)0.0039 (16)0.0030 (14)0.0010 (16)
C11A0.0228 (18)0.0174 (19)0.0153 (16)0.0026 (16)0.0057 (14)0.0023 (15)
C12A0.0161 (17)0.0189 (19)0.0156 (15)0.0010 (15)0.0038 (13)0.0017 (15)
C13A0.0210 (18)0.0150 (18)0.0168 (16)0.0014 (16)0.0046 (13)0.0014 (15)
C14A0.0156 (16)0.0180 (19)0.0165 (15)0.0023 (15)0.0035 (13)0.0048 (15)
C15A0.0163 (17)0.024 (2)0.0154 (16)0.0002 (16)0.0011 (13)0.0013 (15)
C16A0.0221 (18)0.0167 (19)0.0189 (16)0.0033 (16)0.0044 (14)0.0019 (15)
C17A0.0180 (17)0.0147 (19)0.0189 (16)0.0001 (15)0.0053 (13)0.0003 (15)
C18A0.0173 (18)0.024 (2)0.0273 (19)0.0035 (17)0.0007 (15)0.0016 (17)
C19A0.0231 (19)0.020 (2)0.0219 (17)0.0019 (17)0.0021 (14)0.0003 (16)
Br1B0.0397 (2)0.0322 (3)0.02182 (19)0.0007 (2)0.00362 (16)0.00159 (18)
Br2B0.01964 (18)0.0264 (2)0.0304 (2)0.00490 (17)0.00142 (15)0.00229 (17)
O1B0.0361 (16)0.0214 (15)0.0344 (15)0.0074 (13)0.0022 (13)0.0013 (13)
O2B0.0202 (14)0.0190 (16)0.0299 (14)0.0024 (13)0.0015 (12)0.0058 (12)
N1B0.0205 (16)0.0222 (18)0.0203 (15)0.0028 (14)0.0035 (12)0.0007 (14)
N2B0.0181 (15)0.0252 (18)0.0178 (14)0.0016 (14)0.0035 (11)0.0028 (13)
C1B0.0184 (18)0.021 (2)0.0294 (19)0.0007 (17)0.0048 (15)0.0011 (17)
C2B0.022 (2)0.020 (2)0.038 (2)0.0057 (18)0.0029 (17)0.0074 (19)
C3B0.0218 (19)0.025 (2)0.029 (2)0.0002 (18)0.0016 (15)0.0111 (18)
C4B0.0221 (19)0.027 (2)0.0227 (17)0.0073 (17)0.0024 (15)0.0021 (17)
C5B0.0186 (18)0.0170 (19)0.0257 (18)0.0010 (16)0.0036 (14)0.0027 (16)
C6B0.0169 (17)0.019 (2)0.0221 (17)0.0030 (16)0.0030 (13)0.0014 (16)
C7B0.0150 (17)0.0178 (19)0.0234 (17)0.0018 (15)0.0052 (14)0.0034 (16)
C8B0.0181 (17)0.023 (2)0.0243 (17)0.0025 (17)0.0023 (14)0.0014 (17)
C9B0.0155 (17)0.022 (2)0.0234 (17)0.0019 (16)0.0030 (14)0.0031 (16)
C10B0.0210 (18)0.024 (2)0.0204 (17)0.0026 (17)0.0037 (14)0.0003 (16)
C11B0.0200 (18)0.019 (2)0.0194 (17)0.0048 (16)0.0037 (14)0.0011 (15)
C12B0.0171 (17)0.020 (2)0.0149 (15)0.0001 (16)0.0004 (13)0.0013 (15)
C13B0.0222 (19)0.018 (2)0.0203 (17)0.0013 (16)0.0020 (14)0.0023 (16)
C14B0.0170 (17)0.020 (2)0.0187 (16)0.0024 (16)0.0025 (13)0.0053 (16)
C15B0.0184 (18)0.024 (2)0.0207 (17)0.0037 (17)0.0004 (14)0.0014 (16)
C16B0.026 (2)0.017 (2)0.0205 (17)0.0018 (17)0.0038 (15)0.0012 (16)
C17B0.0231 (19)0.019 (2)0.0162 (16)0.0003 (16)0.0048 (14)0.0010 (15)
C18B0.0200 (19)0.028 (2)0.0261 (19)0.0019 (18)0.0016 (15)0.0024 (18)
C19B0.0210 (19)0.024 (2)0.0267 (19)0.0024 (17)0.0050 (15)0.0042 (17)
Geometric parameters (Å, º) top
Br1A—C4A1.899 (3)Br1B—C4B1.906 (4)
Br2A—C14A1.899 (3)Br2B—C14B1.902 (4)
O1A—C1A1.347 (4)O1B—C1B1.344 (5)
O1A—H1OA0.79 (4)O1B—H1OB0.8464
O2A—C17A1.347 (4)O2B—C17B1.350 (4)
O2A—H2OA0.85 (4)O2B—H2OB0.73 (4)
N1A—C7A1.278 (4)N1B—C7B1.273 (4)
N1A—C8A1.459 (4)N1B—C8B1.460 (4)
N2A—C11A1.276 (4)N2B—C11B1.267 (5)
N2A—C10A1.462 (4)N2B—C10B1.463 (5)
C1A—C2A1.390 (5)C1B—C2B1.393 (5)
C1A—C6A1.397 (5)C1B—C6B1.410 (5)
C2A—C3A1.378 (5)C2B—C3B1.374 (6)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.387 (5)C3B—C4B1.381 (6)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.372 (5)C4B—C5B1.381 (5)
C5A—C6A1.407 (5)C5B—C6B1.402 (5)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.454 (5)C6B—C7B1.460 (5)
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C9A1.536 (5)C8B—C9B1.540 (5)
C8A—H8AA0.9900C8B—H8BA0.9900
C8A—H8AB0.9900C8B—H8BB0.9900
C9A—C19A1.524 (5)C9B—C19B1.527 (5)
C9A—C18A1.528 (5)C9B—C18B1.533 (5)
C9A—C10A1.534 (5)C9B—C10B1.534 (5)
C10A—H10A0.9900C10B—H10C0.9900
C10A—H10B0.9900C10B—H10D0.9900
C11A—C12A1.466 (5)C11B—C12B1.458 (5)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.403 (5)C12B—C13B1.393 (5)
C12A—C17A1.405 (5)C12B—C17B1.407 (5)
C13A—C14A1.379 (5)C13B—C14B1.376 (5)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.391 (5)C14B—C15B1.385 (5)
C15A—C16A1.371 (5)C15B—C16B1.376 (5)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.395 (5)C16B—C17B1.391 (5)
C16A—H16A0.9500C16B—H16B0.9500
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
C19A—H19A0.9800C19B—H19D0.9800
C19A—H19B0.9800C19B—H19E0.9800
C19A—H19C0.9800C19B—H19F0.9800
C1A—O1A—H1OA104 (3)C1B—O1B—H1OB105.1
C17A—O2A—H2OA104 (3)C17B—O2B—H2OB109 (4)
C7A—N1A—C8A119.7 (3)C7B—N1B—C8B119.5 (3)
C11A—N2A—C10A119.0 (3)C11B—N2B—C10B118.2 (3)
O1A—C1A—C2A118.2 (3)O1B—C1B—C2B118.7 (4)
O1A—C1A—C6A121.9 (3)O1B—C1B—C6B121.7 (3)
C2A—C1A—C6A119.9 (3)C2B—C1B—C6B119.6 (4)
C3A—C2A—C1A120.5 (4)C3B—C2B—C1B120.5 (4)
C3A—C2A—H2AA119.7C3B—C2B—H2BA119.7
C1A—C2A—H2AA119.7C1B—C2B—H2BA119.8
C2A—C3A—C4A119.8 (3)C2B—C3B—C4B120.0 (3)
C2A—C3A—H3AA120.1C2B—C3B—H3BA120.0
C4A—C3A—H3AA120.1C4B—C3B—H3BA120.0
C5A—C4A—C3A120.7 (3)C3B—C4B—C5B121.2 (4)
C5A—C4A—Br1A119.9 (3)C3B—C4B—Br1B119.0 (3)
C3A—C4A—Br1A119.4 (3)C5B—C4B—Br1B119.8 (3)
C4A—C5A—C6A120.0 (3)C4B—C5B—C6B119.5 (4)
C4A—C5A—H5AA120.0C4B—C5B—H5BA120.2
C6A—C5A—H5AA120.0C6B—C5B—H5BA120.2
C1A—C6A—C5A119.1 (3)C5B—C6B—C1B119.2 (3)
C1A—C6A—C7A121.3 (3)C5B—C6B—C7B119.8 (3)
C5A—C6A—C7A119.7 (3)C1B—C6B—C7B121.0 (3)
N1A—C7A—C6A120.5 (4)N1B—C7B—C6B120.8 (3)
N1A—C7A—H7AA119.8N1B—C7B—H7BA119.6
C6A—C7A—H7AA119.8C6B—C7B—H7BA119.6
N1A—C8A—C9A110.9 (3)N1B—C8B—C9B110.8 (3)
N1A—C8A—H8AA109.5N1B—C8B—H8BA109.5
C9A—C8A—H8AA109.5C9B—C8B—H8BA109.5
N1A—C8A—H8AB109.5N1B—C8B—H8BB109.5
C9A—C8A—H8AB109.5C9B—C8B—H8BB109.5
H8AA—C8A—H8AB108.0H8BA—C8B—H8BB108.1
C19A—C9A—C18A110.1 (3)C19B—C9B—C18B109.6 (3)
C19A—C9A—C10A110.2 (3)C19B—C9B—C10B110.8 (3)
C18A—C9A—C10A107.8 (3)C18B—C9B—C10B107.7 (3)
C19A—C9A—C8A111.2 (3)C19B—C9B—C8B111.0 (3)
C18A—C9A—C8A109.8 (3)C18B—C9B—C8B109.5 (3)
C10A—C9A—C8A107.7 (3)C10B—C9B—C8B108.1 (3)
N2A—C10A—C9A112.1 (3)N2B—C10B—C9B112.9 (3)
N2A—C10A—H10A109.2N2B—C10B—H10C109.0
C9A—C10A—H10A109.2C9B—C10B—H10C109.0
N2A—C10A—H10B109.2N2B—C10B—H10D109.0
C9A—C10A—H10B109.2C9B—C10B—H10D109.0
H10A—C10A—H10B107.9H10C—C10B—H10D107.8
N2A—C11A—C12A120.7 (3)N2B—C11B—C12B121.6 (4)
N2A—C11A—H11A119.7N2B—C11B—H11B119.2
C12A—C11A—H11A119.7C12B—C11B—H11B119.2
C13A—C12A—C17A119.2 (3)C13B—C12B—C17B119.1 (3)
C13A—C12A—C11A119.9 (3)C13B—C12B—C11B120.1 (3)
C17A—C12A—C11A120.9 (3)C17B—C12B—C11B120.7 (3)
C14A—C13A—C12A120.1 (3)C14B—C13B—C12B120.2 (4)
C14A—C13A—H13A119.9C14B—C13B—H13B119.9
C12A—C13A—H13A119.9C12B—C13B—H13B119.9
C13A—C14A—C15A120.8 (3)C13B—C14B—C15B120.8 (3)
C13A—C14A—Br2A120.2 (3)C13B—C14B—Br2B119.8 (3)
C15A—C14A—Br2A119.0 (2)C15B—C14B—Br2B119.4 (3)
C16A—C15A—C14A119.3 (3)C16B—C15B—C14B119.7 (3)
C16A—C15A—H15A120.3C16B—C15B—H15B120.1
C14A—C15A—H15A120.3C14B—C15B—H15B120.1
C15A—C16A—C17A121.4 (3)C15B—C16B—C17B120.6 (4)
C15A—C16A—H16A119.3C15B—C16B—H16B119.7
C17A—C16A—H16A119.3C17B—C16B—H16B119.7
O2A—C17A—C16A119.1 (3)O2B—C17B—C16B119.0 (3)
O2A—C17A—C12A121.8 (3)O2B—C17B—C12B121.5 (3)
C16A—C17A—C12A119.1 (3)C16B—C17B—C12B119.5 (3)
C9A—C18A—H18A109.5C9B—C18B—H18D109.5
C9A—C18A—H18B109.5C9B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C9A—C18A—H18C109.5C9B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C9A—C19A—H19A109.5C9B—C19B—H19D109.5
C9A—C19A—H19B109.5C9B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C9A—C19A—H19C109.5C9B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
O1A—C1A—C2A—C3A178.1 (3)O1B—C1B—C2B—C3B177.9 (3)
C6A—C1A—C2A—C3A2.1 (5)C6B—C1B—C2B—C3B2.1 (6)
C1A—C2A—C3A—C4A0.7 (6)C1B—C2B—C3B—C4B0.4 (6)
C2A—C3A—C4A—C5A0.6 (5)C2B—C3B—C4B—C5B1.2 (6)
C2A—C3A—C4A—Br1A180.0 (3)C2B—C3B—C4B—Br1B178.4 (3)
C3A—C4A—C5A—C6A0.5 (5)C3B—C4B—C5B—C6B1.0 (6)
Br1A—C4A—C5A—C6A179.9 (3)Br1B—C4B—C5B—C6B178.6 (3)
O1A—C1A—C6A—C5A178.0 (3)C4B—C5B—C6B—C1B0.7 (5)
C2A—C1A—C6A—C5A2.1 (5)C4B—C5B—C6B—C7B179.8 (3)
O1A—C1A—C6A—C7A3.9 (5)O1B—C1B—C6B—C5B177.7 (3)
C2A—C1A—C6A—C7A176.0 (3)C2B—C1B—C6B—C5B2.2 (5)
C4A—C5A—C6A—C1A0.9 (5)O1B—C1B—C6B—C7B1.7 (5)
C4A—C5A—C6A—C7A177.2 (3)C2B—C1B—C6B—C7B178.3 (3)
C8A—N1A—C7A—C6A176.5 (3)C8B—N1B—C7B—C6B178.6 (3)
C1A—C6A—C7A—N1A4.1 (5)C5B—C6B—C7B—N1B175.9 (3)
C5A—C6A—C7A—N1A177.8 (3)C1B—C6B—C7B—N1B3.6 (5)
C7A—N1A—C8A—C9A122.4 (4)C7B—N1B—C8B—C9B126.7 (4)
N1A—C8A—C9A—C19A56.1 (4)N1B—C8B—C9B—C19B56.8 (4)
N1A—C8A—C9A—C18A66.0 (4)N1B—C8B—C9B—C18B64.4 (4)
N1A—C8A—C9A—C10A176.9 (3)N1B—C8B—C9B—C10B178.5 (3)
C11A—N2A—C10A—C9A136.7 (3)C11B—N2B—C10B—C9B119.8 (4)
C19A—C9A—C10A—N2A57.3 (4)C19B—C9B—C10B—N2B59.5 (4)
C18A—C9A—C10A—N2A177.5 (3)C18B—C9B—C10B—N2B179.4 (3)
C8A—C9A—C10A—N2A64.2 (4)C8B—C9B—C10B—N2B62.3 (4)
C10A—N2A—C11A—C12A176.9 (3)C10B—N2B—C11B—C12B179.4 (3)
N2A—C11A—C12A—C13A179.2 (3)N2B—C11B—C12B—C13B172.0 (3)
N2A—C11A—C12A—C17A1.9 (5)N2B—C11B—C12B—C17B8.8 (5)
C17A—C12A—C13A—C14A2.0 (5)C17B—C12B—C13B—C14B1.0 (5)
C11A—C12A—C13A—C14A175.4 (3)C11B—C12B—C13B—C14B178.2 (3)
C12A—C13A—C14A—C15A0.1 (5)C12B—C13B—C14B—C15B0.9 (5)
C12A—C13A—C14A—Br2A178.7 (3)C12B—C13B—C14B—Br2B178.3 (3)
C13A—C14A—C15A—C16A1.4 (5)C13B—C14B—C15B—C16B1.3 (5)
Br2A—C14A—C15A—C16A179.8 (3)Br2B—C14B—C15B—C16B177.9 (3)
C14A—C15A—C16A—C17A0.9 (5)C14B—C15B—C16B—C17B0.2 (5)
C15A—C16A—C17A—O2A178.9 (3)C15B—C16B—C17B—O2B178.5 (3)
C15A—C16A—C17A—C12A1.0 (5)C15B—C16B—C17B—C12B2.0 (5)
C13A—C12A—C17A—O2A177.5 (3)C13B—C12B—C17B—O2B178.1 (3)
C11A—C12A—C17A—O2A5.2 (5)C11B—C12B—C17B—O2B2.7 (5)
C13A—C12A—C17A—C16A2.4 (5)C13B—C12B—C17B—C16B2.4 (5)
C11A—C12A—C17A—C16A174.9 (3)C11B—C12B—C17B—C16B176.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1OB···N1B0.851.812.580 (4)151
O2A—H2OA···N2A0.85 (4)1.79 (4)2.578 (4)154 (4)
O1A—H1OA···N1A0.79 (5)1.85 (5)2.572 (4)153 (4)
O2B—H2OB···N2B0.73 (5)1.94 (5)2.586 (4)149 (5)
C8A—H8AA···N2A0.992.582.960 (4)103
C8B—H8BA···N2B0.992.602.966 (4)102
C16B—H16B···O2Bi0.952.583.290 (5)131
C19A—H19B···N1A0.982.582.918 (4)100
C19A—H19C···N2A0.982.582.933 (5)101
C19B—H19F···N1B0.982.602.926 (5)100
C7B—H7BA···Cg1ii0.952.963.571 (4)123
C18B—H18D···Cg2iii0.982.773.652 (4)151
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x, y1, z1/2.

Experimental details

Crystal data
Chemical formulaC19H20Br2N2O2
Mr468.19
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)31.7684 (10), 6.2436 (2), 38.7287 (11)
β (°) 99.870 (2)
V3)7568.1 (4)
Z16
Radiation typeMo Kα
µ (mm1)4.30
Crystal size (mm)0.52 × 0.10 × 0.06
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.213, 0.783
No. of measured, independent and
observed [I > 2σ(I)] reflections
47391, 11172, 6920
Rint0.080
(sin θ/λ)max1)0.708
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.110, 1.01
No. of reflections11172
No. of parameters463
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.57, 0.46

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1OB···N1B0.85001.81002.580 (4)151.00
O2A—H2OA···N2A0.85 (4)1.79 (4)2.578 (4)154 (4)
O1A—H1OA···N1A0.79 (5)1.85 (5)2.572 (4)153 (4)
O2B—H2OB···N2B0.73 (5)1.94 (5)2.586 (4)149 (5)
C8A—H8AA···N2A0.99002.58002.960 (4)103.00
C8B—H8BA···N2B0.99002.60002.966 (4)102.00
C16B—H16B···O2Bi0.95002.58003.290 (5)131.00
C19A—H19B···N1A0.98002.58002.918 (4)100.00
C19A—H19C···N2A0.98002.58002.933 (5)101.00
C19B—H19F···N1B0.98002.60002.926 (5)100.00
C7B—H7BA···Cg1ii0.95002.96003.571 (4)123.00
C18B—H18D···Cg2iii0.98002.77003.652 (4)151.00
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x, y1, z1/2.
 

Footnotes

Additional correspondence author, tel: +98-352-7220011 ext. 157, fax: 98-352-7228110, e-mail: hkargar@pnu.ac.ir.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund (grant No. 305/PFIZIK/613312). RK thanks Universiti Sains Malaysia for an award of a post-doctoral research fellowship. HK thanks PNU for financial support.

References

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Volume 64| Part 10| October 2008| Pages o1895-o1896
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