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 June 1; 65(Pt 6): o1221–o1222.
Published online 2009 May 7. doi:  10.1107/S1600536809016225
PMCID: PMC2969738

1-[(Bromo­meth­yl)(phen­yl)meth­ylene]-2-(2,4-dinitro­phen­yl)hydrazine

Abstract

The title compound, C14H11BrN4O4, comprises two crystallographically independent mol­ecules (A and B) in the asymmetric unit. In mol­ecule B, intra­molecular bifurcated N—H(...)O and N—H(...)Br hydrogen bonds and in mol­ecule A, an intra­molecular N—H(...)O hydrogen bond generate S(6) ring motifs. The dihedral angle between the phenyl and benzene rings is 5.44 (6) in mol­ecule A and 7.63 (6)° in mol­ecule B. The ortho- and meta-nitro substituents make dihedral angles of 6.67 (15) and 2.26 (15)° to the attached benzene ring in mol­ecule A and 6.37 (17) and 5.81 (16)° in mol­ecule B. The Br atom in mol­ecule B is disordered over two positions with a refined site-occupancy ratio of 0.61 (3):0.39 (3). Inter­esting features of the crystal structure are the short Br(...)N [3.257 (3)–3.294 (4) Å], Br(...)O [3.279 (3)–3.307 (4) Å] and O(...)O [2.9319 (16)–2.9995 (16) Å] contacts, which are shorter than the sum of the van der Waals radii of these atoms. The crystal structure is further stabilized by inter­molecular C—H(...)O and π–π inter­actions [centroid–centroid distances = 3.6643 (8)–3.8514 (8) Å].

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For related structures and bioactivity, see; for example: Salhin et al. (2007 [triangle]); Tameem et al. (2006 [triangle], 2007 [triangle], 2008 [triangle]); Rollas & Küçükgüzel (2007 [triangle]); Shao et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1221-scheme1.jpg

Experimental

Crystal data

  • C14H11BrN4O4
  • M r = 379.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1221-efi1.jpg
  • a = 13.0803 (3) Å
  • b = 15.3626 (3) Å
  • c = 14.1512 (2) Å
  • β = 91.903 (1)°
  • V = 2842.08 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.92 mm−1
  • T = 100 K
  • 0.59 × 0.34 × 0.33 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.238, T max = 0.381
  • 45788 measured reflections
  • 11112 independent reflections
  • 8666 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.077
  • S = 1.01
  • 11112 reflections
  • 433 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.69 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016225/at2763sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016225/at2763Isup2.hkl

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

Acknowledgments

We thank the Malysian Government and Universiti Sains Malaysia for the Science Fund grant No. 1001/229/PKIMIA/811055.

supplementary crystallographic information

Comment

In view of the importance of hydrazone derivatives in chemical and biological applications (Rollas & Küçükgüzel, 2007; Shao et al., 2008), a series of hydrazone derivatives has been prepared in our laboratory, from which several X-ray structures have been reported (Salhin et al., 2007; Tameem et al., 2006, 2007 and 2008).

The title compound, C14H11BrN4O4, comprises two crystallographically independent molecules (A, B) in the asymmetric unit. In molecule B, intramolecular bifurcated N—H···O and N—H···Br hydrogen bonds and in molecule A, an intramolecular N—H···O hydrogen bond generate S(6) ring motifs. The dihedral angle between the phenyl rings in molecules A and B are 5.44 (6) and 7.63 (6)°, respectively. The ortho and meta nitro-substituents make the dihedral angles of 6.67 (15) and 2.26 (15)° in molecule A and 6.37917) and 5.81 (16)° to the benzene ring they are attached. The bromine group was disordered over two positins with a refined site-occupancy ratio of 0.61 (3)/0.39 (3) in molecule B. The crystal structure is further stabilized by intermolecular C—H···O and π-π [Cg1··· Cg1iii = 3.6643 (8) Å, (iii) 2 - x, -y, 1 - z; Cg1··· Cg4iv = 3.7308 (8) Å, (iv) 1 - x, -y, 1 - z; Cg1···Cg2iv = 3.7013 (8) Å; Cg2···Cg3iv = 3.7012 (8) Å; Cg3···Cg4v = 3.8514 (8) Å, (v) -x, -y, 2 - z: Cg1, Cg2, Cg3, Cg4 are the centroids of the C1A–C6A, C8A–C13A, C1B–C6B, and C8B–C13b rings].

The interesting features of the crystal structure are short Br1A···N4Avi [3.257 (3), (vi) 3/2-x,1/2+y,1/2-z], Br1C···N4Avi [3.294 (4) Å], Br1A···O3Aviii [3.279 (3), (viii) 3/2-x,-1/2+y,1/2-z], Br1C···O3Avii [3.307 (4) Å], O2A···O3Aiv [2.9319 (16) Å], and O1A···O4Bvii [2.9995(160 Å, (vii) 1/2-x,1/2+y,3/2-z] contacts which are shorter than the sum of the van der Waals radii of these atoms.

Experimental

2,4-Dinitrophenylhydrazine (0.5 g, 2.5 mmol) was dissolved in ethanol (10 ml), and H2SO4 solution (98%, 1 ml) was added slowly with stirring. The solution was heated on a water bath for several minutes until it cleared. An ethanol solution (5 ml) of α-bromoacetophenone (0.5 g, 2.5 mmol) was dropped slowly into the above solution with continuous stirring. The mixture was heated for another 5 minutes on water bath. On cooling to room temperature, an orange precipitate was formed. Recrystallization from ethanol solution produced the crystals of the title compound.

Refinement

The N-bound hydrogen atoms were located from the difference Fourier map and refined freely, see Table 1. The rest of the H atoms were positioned geometrically and refined as riding model with C—H = 0.93–0.97 and Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.
Fig. 2.
The crystal packing of the title compound, viewed down the c-axis showing intermolecular interactions. Intermolecular interactions are shown as dashed lines.

Crystal data

C14H11BrN4O4F(000) = 1520
Mr = 379.18Dx = 1.772 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9995 reflections
a = 13.0803 (3) Åθ = 2.2–33.8°
b = 15.3626 (3) ŵ = 2.92 mm1
c = 14.1512 (2) ÅT = 100 K
β = 91.903 (1)°Block, orange
V = 2842.08 (9) Å30.59 × 0.34 × 0.33 mm
Z = 8

Data collection

Bruker SMART APEXII CCD area-detector diffractometer11112 independent reflections
Radiation source: fine-focus sealed tube8666 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 33.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −19→20
Tmin = 0.238, Tmax = 0.381k = −23→20
45788 measured reflectionsl = −21→21

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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0364P)2 + 1.0321P] where P = (Fo2 + 2Fc2)/3
11112 reflections(Δ/σ)max = 0.007
433 parametersΔρmax = 0.69 e Å3
0 restraintsΔρmin = −0.34 e Å3

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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*/UeqOcc. (<1)
Br1C0.9686 (2)0.1986 (2)0.2704 (3)0.0201 (6)0.39 (3)
Br1A0.9789 (4)0.20086 (17)0.2662 (2)0.0351 (3)0.61 (3)
O1A0.73417 (8)0.13615 (7)0.39559 (8)0.0233 (2)
O2A0.57980 (8)0.08996 (7)0.41372 (8)0.0265 (2)
O3A0.49748 (9)−0.20591 (8)0.44038 (8)0.0278 (2)
O4A0.61595 (9)−0.30399 (7)0.45462 (8)0.0279 (2)
N1A0.98576 (9)0.00033 (8)0.38344 (8)0.0160 (2)
N2A0.88776 (9)0.02751 (8)0.39522 (8)0.0169 (2)
N3A0.67186 (9)0.07666 (8)0.40818 (8)0.0184 (2)
N4A0.58779 (10)−0.22801 (8)0.44372 (8)0.0214 (2)
C1A1.23883 (10)0.08672 (9)0.33786 (9)0.0182 (2)
H1AA1.22510.14600.33290.022*
C2A1.33726 (11)0.05613 (10)0.32338 (10)0.0207 (3)
H2AA1.38900.09510.30940.025*
C3A1.35843 (11)−0.03208 (10)0.32978 (10)0.0210 (3)
H3AA1.4242−0.05240.31990.025*
C4A1.28092 (11)−0.09024 (10)0.35096 (10)0.0204 (3)
H4AA1.2951−0.14950.35530.024*
C5A1.18284 (10)−0.06035 (9)0.36562 (9)0.0177 (2)
H5AA1.1314−0.09970.37940.021*
C6A1.16034 (10)0.02883 (8)0.35980 (9)0.0149 (2)
C7A1.05537 (10)0.05985 (8)0.37716 (9)0.0154 (2)
C8A0.81403 (10)−0.03332 (8)0.40698 (9)0.0155 (2)
C9A0.84032 (10)−0.12258 (9)0.41293 (9)0.0171 (2)
H9AA0.9084−0.13880.40810.021*
C10A0.76784 (11)−0.18574 (9)0.42569 (9)0.0188 (2)
H10A0.7866−0.24410.42940.023*
C11A0.66562 (11)−0.16139 (9)0.43304 (9)0.0179 (2)
C12A0.63592 (10)−0.07562 (9)0.42875 (9)0.0177 (2)
H12A0.5676−0.06050.43480.021*
C13A0.70905 (10)−0.01200 (9)0.41530 (9)0.0163 (2)
C14A1.03381 (11)0.15508 (9)0.38699 (9)0.0179 (2)
H14A0.98970.16450.43890.022*0.61 (3)
H14B1.09650.18600.39980.022*0.61 (3)
H14E1.09570.18540.40490.022*0.39 (3)
H14F0.98530.16410.43550.022*0.39 (3)
Br1B0.013792 (12)0.244826 (9)0.748873 (10)0.02245 (4)
O1B−0.22221 (8)0.18339 (7)0.85993 (8)0.0230 (2)
O2B−0.37193 (9)0.14659 (8)0.90464 (11)0.0387 (3)
O3B−0.46689 (8)−0.14664 (8)0.95307 (9)0.0301 (2)
O4B−0.35034 (9)−0.24598 (7)0.97032 (9)0.0286 (2)
N1B0.02449 (9)0.04055 (8)0.85746 (8)0.0164 (2)
N2B−0.07206 (9)0.07090 (8)0.86865 (8)0.0172 (2)
N3B−0.28334 (9)0.12826 (8)0.88791 (9)0.0201 (2)
N4B−0.37744 (9)−0.17037 (8)0.95376 (8)0.0200 (2)
C1B0.28568 (10)0.11582 (9)0.82555 (9)0.0181 (2)
H1BA0.27730.17590.82360.022*
C2B0.38267 (10)0.07996 (9)0.81648 (10)0.0202 (3)
H2BA0.43870.11630.80910.024*
C3B0.39609 (11)−0.00974 (10)0.81839 (10)0.0202 (3)
H3BA0.4609−0.03360.81240.024*
C4B0.31187 (11)−0.06353 (9)0.82929 (10)0.0211 (3)
H4BA0.3204−0.12360.83000.025*
C5B0.21560 (11)−0.02835 (9)0.83908 (10)0.0189 (3)
H5BA0.1599−0.06510.84670.023*
C6B0.20080 (10)0.06198 (8)0.83760 (9)0.0150 (2)
C7B0.09677 (10)0.09733 (8)0.85066 (9)0.0153 (2)
C8B−0.14694 (10)0.01355 (8)0.88991 (9)0.0151 (2)
C9B−0.12331 (10)−0.07567 (9)0.90438 (9)0.0169 (2)
H9BA−0.0560−0.09430.90000.020*
C10B−0.19764 (10)−0.13504 (9)0.92470 (9)0.0176 (2)
H10B−0.1811−0.19350.93290.021*
C11B−0.29861 (10)−0.10694 (9)0.93296 (9)0.0165 (2)
C12B−0.32537 (10)−0.02108 (9)0.92251 (9)0.0169 (2)
H12B−0.3926−0.00330.93010.020*
C13B−0.25005 (10)0.03894 (9)0.90035 (9)0.0158 (2)
C14B0.07976 (10)0.19299 (9)0.86268 (10)0.0183 (2)
H14C0.14490.22140.87570.022*
H14D0.03700.20260.91640.022*
H1NB−0.0909 (14)0.1209 (13)0.8571 (13)0.026 (5)*
H1NA0.8714 (15)0.0766 (14)0.3890 (14)0.033 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br1C0.0235 (14)0.0151 (5)0.0216 (5)0.0021 (5)−0.0005 (4)0.0042 (4)
Br1A0.0622 (9)0.0206 (5)0.0219 (3)0.0145 (5)−0.0070 (5)0.0008 (3)
O1A0.0180 (5)0.0153 (5)0.0366 (6)0.0002 (4)−0.0001 (4)0.0009 (4)
O2A0.0153 (5)0.0257 (6)0.0385 (6)0.0054 (4)0.0024 (4)0.0008 (5)
O3A0.0225 (5)0.0295 (6)0.0319 (6)−0.0083 (4)0.0058 (4)−0.0021 (5)
O4A0.0369 (6)0.0174 (5)0.0295 (5)−0.0069 (4)0.0016 (5)0.0009 (4)
N1A0.0132 (5)0.0166 (5)0.0183 (5)0.0016 (4)0.0011 (4)0.0005 (4)
N2A0.0151 (5)0.0134 (5)0.0223 (5)0.0013 (4)0.0014 (4)0.0004 (4)
N3A0.0170 (5)0.0175 (5)0.0206 (5)0.0021 (4)−0.0008 (4)−0.0011 (4)
N4A0.0263 (6)0.0212 (6)0.0169 (5)−0.0075 (5)0.0036 (4)−0.0019 (4)
C1A0.0192 (6)0.0157 (6)0.0196 (6)−0.0024 (5)0.0011 (5)0.0004 (5)
C2A0.0166 (6)0.0243 (7)0.0215 (6)−0.0056 (5)0.0022 (5)0.0000 (5)
C3A0.0157 (6)0.0265 (7)0.0210 (6)0.0021 (5)0.0016 (5)−0.0002 (5)
C4A0.0194 (6)0.0180 (6)0.0237 (6)0.0037 (5)0.0005 (5)0.0001 (5)
C5A0.0166 (6)0.0153 (6)0.0212 (6)−0.0008 (5)0.0009 (5)0.0007 (5)
C6A0.0148 (6)0.0148 (6)0.0150 (5)−0.0004 (4)−0.0006 (4)−0.0003 (4)
C7A0.0165 (6)0.0138 (6)0.0160 (5)0.0013 (4)−0.0002 (4)0.0002 (4)
C8A0.0153 (6)0.0158 (6)0.0155 (5)0.0000 (4)−0.0001 (4)−0.0003 (4)
C9A0.0174 (6)0.0165 (6)0.0176 (5)0.0024 (5)0.0024 (4)−0.0011 (4)
C10A0.0240 (6)0.0153 (6)0.0172 (6)−0.0004 (5)0.0013 (5)−0.0009 (4)
C11A0.0210 (6)0.0171 (6)0.0156 (5)−0.0044 (5)0.0020 (5)−0.0007 (4)
C12A0.0162 (6)0.0208 (6)0.0161 (5)−0.0016 (5)0.0002 (4)−0.0013 (5)
C13A0.0166 (6)0.0155 (6)0.0169 (5)0.0011 (5)0.0005 (4)−0.0004 (4)
C14A0.0190 (6)0.0161 (6)0.0186 (6)0.0011 (5)−0.0003 (5)−0.0003 (4)
Br1B0.02671 (7)0.01604 (7)0.02483 (7)0.00470 (5)0.00414 (5)0.00186 (5)
O1B0.0200 (5)0.0146 (5)0.0345 (6)0.0001 (4)0.0014 (4)0.0018 (4)
O2B0.0189 (5)0.0243 (6)0.0738 (9)0.0085 (5)0.0131 (6)0.0068 (6)
O3B0.0159 (5)0.0297 (6)0.0446 (7)−0.0018 (4)0.0024 (4)0.0081 (5)
O4B0.0277 (6)0.0174 (5)0.0410 (7)−0.0017 (4)0.0071 (5)0.0046 (4)
N1B0.0132 (5)0.0160 (5)0.0200 (5)0.0013 (4)0.0017 (4)−0.0007 (4)
N2B0.0137 (5)0.0134 (5)0.0245 (5)0.0016 (4)0.0025 (4)−0.0003 (4)
N3B0.0174 (5)0.0158 (5)0.0272 (6)0.0027 (4)0.0011 (4)−0.0003 (4)
N4B0.0190 (5)0.0214 (6)0.0197 (5)−0.0031 (4)0.0022 (4)0.0011 (4)
C1B0.0182 (6)0.0151 (6)0.0211 (6)−0.0017 (5)0.0024 (5)−0.0008 (5)
C2B0.0154 (6)0.0209 (7)0.0243 (6)−0.0029 (5)0.0030 (5)−0.0009 (5)
C3B0.0158 (6)0.0228 (7)0.0220 (6)0.0035 (5)0.0020 (5)0.0010 (5)
C4B0.0191 (6)0.0162 (6)0.0280 (7)0.0028 (5)0.0029 (5)0.0019 (5)
C5B0.0167 (6)0.0155 (6)0.0247 (6)−0.0011 (5)0.0029 (5)0.0009 (5)
C6B0.0149 (6)0.0148 (6)0.0152 (5)−0.0001 (4)0.0006 (4)−0.0011 (4)
C7B0.0160 (6)0.0135 (6)0.0163 (5)0.0003 (4)0.0009 (4)−0.0013 (4)
C8B0.0142 (6)0.0154 (6)0.0157 (5)0.0007 (4)0.0006 (4)−0.0015 (4)
C9B0.0152 (6)0.0153 (6)0.0202 (6)0.0024 (5)0.0009 (4)−0.0002 (4)
C10B0.0189 (6)0.0148 (6)0.0192 (6)0.0015 (5)0.0014 (5)0.0001 (4)
C11B0.0150 (6)0.0179 (6)0.0167 (5)−0.0015 (5)0.0006 (4)0.0014 (4)
C12B0.0141 (6)0.0189 (6)0.0179 (6)0.0008 (5)0.0012 (4)−0.0003 (4)
C13B0.0145 (6)0.0143 (6)0.0186 (6)0.0023 (4)0.0003 (4)−0.0005 (4)
C14B0.0179 (6)0.0150 (6)0.0221 (6)0.0003 (5)0.0014 (5)−0.0023 (5)

Geometric parameters (Å, °)

Br1C—C14A1.949 (4)C14A—H14F0.9601
Br1A—C14A1.962 (3)Br1B—C14B1.9699 (14)
O1A—N3A1.2413 (15)O1B—N3B1.2388 (16)
O2A—N3A1.2265 (15)O2B—N3B1.2232 (16)
O3A—N4A1.2286 (17)O3B—N4B1.2252 (16)
O4A—N4A1.2321 (17)O4B—N4B1.2347 (16)
N1A—C7A1.2955 (17)N1B—C7B1.2922 (17)
N1A—N2A1.3636 (16)N1B—N2B1.3604 (16)
N2A—C8A1.3572 (17)N2B—C8B1.3584 (17)
N2A—H1NA0.79 (2)N2B—H1NB0.82 (2)
N3A—C13A1.4487 (17)N3B—C13B1.4486 (17)
N4A—C11A1.4549 (18)N4B—C11B1.4559 (18)
C1A—C2A1.392 (2)C1B—C2B1.3928 (19)
C1A—C6A1.4010 (18)C1B—C6B1.3995 (18)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.386 (2)C2B—C3B1.389 (2)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.392 (2)C3B—C4B1.390 (2)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.3847 (19)C4B—C5B1.382 (2)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.4031 (19)C5B—C6B1.4011 (19)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.4816 (18)C6B—C7B1.4824 (18)
C7A—C14A1.4973 (18)C7B—C14B1.4969 (18)
C8A—C9A1.4155 (19)C8B—C13B1.4164 (18)
C8A—C13A1.4205 (19)C8B—C9B1.4185 (18)
C9A—C10A1.3727 (19)C9B—C10B1.3706 (19)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.396 (2)C10B—C11B1.3980 (19)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.375 (2)C11B—C12B1.3714 (19)
C12A—C13A1.3851 (19)C12B—C13B1.3928 (19)
C12A—H12A0.9300C12B—H12B0.9300
C14A—H14A0.9600C14B—H14C0.9700
C14A—H14B0.9600C14B—H14D0.9700
C14A—H14E0.9600
C7A—N1A—N2A117.26 (11)H14A—C14A—H14E104.4
C8A—N2A—N1A118.61 (11)C7A—C14A—H14F109.8
C8A—N2A—H1NA118.8 (15)Br1C—C14A—H14F106.0
N1A—N2A—H1NA122.1 (15)Br1A—C14A—H14F109.9
O2A—N3A—O1A122.50 (12)H14B—C14A—H14F112.0
O2A—N3A—C13A118.70 (12)H14E—C14A—H14F108.2
O1A—N3A—C13A118.80 (11)C7B—N1B—N2B117.50 (11)
O3A—N4A—O4A123.35 (13)C8B—N2B—N1B118.85 (11)
O3A—N4A—C11A118.47 (13)C8B—N2B—H1NB115.9 (13)
O4A—N4A—C11A118.17 (12)N1B—N2B—H1NB124.8 (14)
C2A—C1A—C6A120.43 (13)O2B—N3B—O1B122.01 (12)
C2A—C1A—H1AA119.8O2B—N3B—C13B118.52 (12)
C6A—C1A—H1AA119.8O1B—N3B—C13B119.46 (11)
C3A—C2A—C1A120.29 (13)O3B—N4B—O4B123.33 (13)
C3A—C2A—H2AA119.9O3B—N4B—C11B118.80 (12)
C1A—C2A—H2AA119.9O4B—N4B—C11B117.86 (12)
C2A—C3A—C4A119.77 (13)C2B—C1B—C6B120.41 (13)
C2A—C3A—H3AA120.1C2B—C1B—H1BA119.8
C4A—C3A—H3AA120.1C6B—C1B—H1BA119.8
C5A—C4A—C3A120.31 (13)C3B—C2B—C1B120.36 (13)
C5A—C4A—H4AA119.8C3B—C2B—H2BA119.8
C3A—C4A—H4AA119.8C1B—C2B—H2BA119.8
C4A—C5A—C6A120.56 (13)C2B—C3B—C4B119.46 (13)
C4A—C5A—H5AA119.7C2B—C3B—H3BA120.3
C6A—C5A—H5AA119.7C4B—C3B—H3BA120.3
C1A—C6A—C5A118.62 (12)C5B—C4B—C3B120.46 (13)
C1A—C6A—C7A121.50 (12)C5B—C4B—H4BA119.8
C5A—C6A—C7A119.87 (12)C3B—C4B—H4BA119.8
N1A—C7A—C6A116.21 (11)C4B—C5B—C6B120.79 (13)
N1A—C7A—C14A123.25 (12)C4B—C5B—H5BA119.6
C6A—C7A—C14A120.54 (12)C6B—C5B—H5BA119.6
N2A—C8A—C9A120.14 (12)C1B—C6B—C5B118.52 (12)
N2A—C8A—C13A122.97 (12)C1B—C6B—C7B122.27 (12)
C9A—C8A—C13A116.88 (12)C5B—C6B—C7B119.20 (12)
C10A—C9A—C8A121.67 (13)N1B—C7B—C6B116.03 (12)
C10A—C9A—H9AA119.2N1B—C7B—C14B122.85 (12)
C8A—C9A—H9AA119.2C6B—C7B—C14B120.95 (11)
C9A—C10A—C11A119.21 (13)N2B—C8B—C13B122.72 (12)
C9A—C10A—H10A120.4N2B—C8B—C9B120.22 (12)
C11A—C10A—H10A120.4C13B—C8B—C9B117.05 (12)
C12A—C11A—C10A121.58 (13)C10B—C9B—C8B121.37 (12)
C12A—C11A—N4A118.77 (13)C10B—C9B—H9BA119.3
C10A—C11A—N4A119.64 (13)C8B—C9B—H9BA119.3
C11A—C12A—C13A119.15 (13)C9B—C10B—C11B119.39 (12)
C11A—C12A—H12A120.4C9B—C10B—H10B120.3
C13A—C12A—H12A120.4C11B—C10B—H10B120.3
C12A—C13A—C8A121.50 (12)C12B—C11B—C10B121.76 (13)
C12A—C13A—N3A116.18 (12)C12B—C11B—N4B119.05 (12)
C8A—C13A—N3A122.30 (12)C10B—C11B—N4B119.18 (12)
C7A—C14A—Br1C109.55 (14)C11B—C12B—C13B118.76 (12)
C7A—C14A—Br1A109.50 (11)C11B—C12B—H12B120.6
C7A—C14A—H14A109.8C13B—C12B—H12B120.6
Br1C—C14A—H14A109.8C12B—C13B—C8B121.62 (12)
Br1A—C14A—H14A113.6C12B—C13B—N3B116.26 (12)
C7A—C14A—H14B109.8C8B—C13B—N3B122.11 (12)
Br1C—C14A—H14B109.7C7B—C14B—Br1B111.51 (9)
Br1A—C14A—H14B105.8C7B—C14B—H14C109.3
H14A—C14A—H14B108.2Br1B—C14B—H14C109.3
C7A—C14A—H14E109.8C7B—C14B—H14D109.3
Br1C—C14A—H14E113.5Br1B—C14B—H14D109.3
Br1A—C14A—H14E109.7H14C—C14B—H14D108.0
C7A—N1A—N2A—C8A−176.60 (12)C6A—C7A—C14A—Br1A98.2 (2)
C6A—C1A—C2A—C3A0.5 (2)C7B—N1B—N2B—C8B−170.40 (12)
C1A—C2A—C3A—C4A−0.1 (2)C6B—C1B—C2B—C3B0.6 (2)
C2A—C3A—C4A—C5A0.0 (2)C1B—C2B—C3B—C4B0.1 (2)
C3A—C4A—C5A—C6A−0.3 (2)C2B—C3B—C4B—C5B−0.6 (2)
C2A—C1A—C6A—C5A−0.80 (19)C3B—C4B—C5B—C6B0.4 (2)
C2A—C1A—C6A—C7A178.94 (12)C2B—C1B—C6B—C5B−0.80 (19)
C4A—C5A—C6A—C1A0.70 (19)C2B—C1B—C6B—C7B177.96 (12)
C4A—C5A—C6A—C7A−179.04 (12)C4B—C5B—C6B—C1B0.3 (2)
N2A—N1A—C7A—C6A−177.18 (11)C4B—C5B—C6B—C7B−178.51 (13)
N2A—N1A—C7A—C14A3.11 (18)N2B—N1B—C7B—C6B−179.43 (11)
C1A—C6A—C7A—N1A170.46 (12)N2B—N1B—C7B—C14B5.26 (19)
C5A—C6A—C7A—N1A−9.80 (18)C1B—C6B—C7B—N1B177.49 (12)
C1A—C6A—C7A—C14A−9.82 (18)C5B—C6B—C7B—N1B−3.76 (18)
C5A—C6A—C7A—C14A169.92 (12)C1B—C6B—C7B—C14B−7.11 (19)
N1A—N2A—C8A—C9A4.05 (18)C5B—C6B—C7B—C14B171.65 (12)
N1A—N2A—C8A—C13A−176.93 (12)N1B—N2B—C8B—C13B−178.28 (12)
N2A—C8A—C9A—C10A179.39 (12)N1B—N2B—C8B—C9B2.88 (18)
C13A—C8A—C9A—C10A0.31 (19)N2B—C8B—C9B—C10B−179.15 (12)
C8A—C9A—C10A—C11A0.0 (2)C13B—C8B—C9B—C10B1.94 (19)
C9A—C10A—C11A—C12A−0.7 (2)C8B—C9B—C10B—C11B−1.1 (2)
C9A—C10A—C11A—N4A178.16 (12)C9B—C10B—C11B—C12B−0.9 (2)
O3A—N4A—C11A—C12A6.17 (18)C9B—C10B—C11B—N4B179.49 (12)
O4A—N4A—C11A—C12A−174.63 (12)O3B—N4B—C11B—C12B6.41 (19)
O3A—N4A—C11A—C10A−172.69 (12)O4B—N4B—C11B—C12B−174.33 (13)
O4A—N4A—C11A—C10A6.51 (18)O3B—N4B—C11B—C10B−173.95 (13)
C10A—C11A—C12A—C13A1.1 (2)O4B—N4B—C11B—C10B5.31 (18)
N4A—C11A—C12A—C13A−177.78 (11)C10B—C11B—C12B—C13B1.9 (2)
C11A—C12A—C13A—C8A−0.76 (19)N4B—C11B—C12B—C13B−178.46 (12)
C11A—C12A—C13A—N3A177.91 (11)C11B—C12B—C13B—C8B−0.99 (19)
N2A—C8A—C13A—C12A−178.96 (12)C11B—C12B—C13B—N3B178.53 (12)
C9A—C8A—C13A—C12A0.09 (19)N2B—C8B—C13B—C12B−179.76 (12)
N2A—C8A—C13A—N3A2.5 (2)C9B—C8B—C13B—C12B−0.88 (19)
C9A—C8A—C13A—N3A−178.49 (11)N2B—C8B—C13B—N3B0.7 (2)
O2A—N3A—C13A—C12A−0.45 (18)C9B—C8B—C13B—N3B179.62 (12)
O1A—N3A—C13A—C12A−179.62 (12)O2B—N3B—C13B—C12B5.65 (19)
O2A—N3A—C13A—C8A178.20 (12)O1B—N3B—C13B—C12B−173.60 (12)
O1A—N3A—C13A—C8A−0.97 (19)O2B—N3B—C13B—C8B−174.83 (14)
N1A—C7A—C14A—Br1C−77.37 (17)O1B—N3B—C13B—C8B5.92 (19)
C6A—C7A—C14A—Br1C102.93 (15)N1B—C7B—C14B—Br1B−77.67 (14)
N1A—C7A—C14A—Br1A−82.1 (2)C6B—C7B—C14B—Br1B107.25 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2B—H1NB···Br1B0.82 (2)2.826 (19)3.3764 (12)126.2 (15)
N2B—H1NB···O1B0.82 (2)1.969 (19)2.6159 (16)135.1 (17)
N2A—H1NA···O1A0.79 (2)2.02 (2)2.6120 (16)131.8 (19)
C2B—H2BA···Br1Ai0.932.933.673 (3)138
C14B—H14C···O1Ai0.972.493.3352 (17)145
C14B—H14D···O3Aii0.972.523.3745 (18)147

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x+1/2, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2763).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Rollas, S. & Küçükgüzel, Ş. G. (2007). Molecules, 12, 1910–1939. [PubMed]
  • Salhin, A., Tameem, A. A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2880.
  • Shao, J., Lin, I., Yu, M., Cai, Z. & Lin, I. (2008). Talanta, 75, 551–555. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Tameem, A. A., Saad, B., Salhin, A. M., Jebas, S. R. & Fun, H.-K. (2008). Acta Cryst. E64, o679–o680. [PMC free article] [PubMed]
  • Tameem, A. A., Salhin, A., Saad, B., Rahman, I. A., Saleh, M. I., Ng, S.-L. & Fun, H.-K. (2006). Acta Cryst. E62, o5686–o5688.
  • Tameem, A. A., Salhin, A., Saad, B., Rahman, I. A., Saleh, M. I., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o57–o58.

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