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 April 1; 65(Pt 4): o883.
Published online 2009 March 28. doi:  10.1107/S1600536809010435
PMCID: PMC2968868

(E)-N′-(5-Bromo-2-methoxy­benzyl­idene)-3-methoxy­benzohydrazide

Abstract

In the title compound, C16H15BrN2O3, there are two independent mol­ecules (A and B) in the asymmetric unit. The major difference between the two mol­ecules is the dihedral angle formed by the aromatic rings [72.6 (2) and 18.8 (2)° for A and B, respectively]. The benzohydrazide groups are not planar and the mol­ecules exist in trans configurations with respect to the methyl­idene units. The mol­ecular packing is stabilized by two inter­molecular N—H(...)O hydrogen bonds, forming chains parallel to the c axis. Only the A mol­ecules of the asymmetric unit are held together by π–π inter­actions [centroid–centroid distance = 3.714 (3) Å].

Related literature

For the biological activities of hydrazones, see: Zhong et al. (2007 [triangle]); Raj et al. (2007 [triangle]); Jimenez-Pulido et al. (2008 [triangle]). For related structures, see: Ban & Li (2008a [triangle],b [triangle]); Yehye et al. (2008 [triangle]); Fun et al. (2008a [triangle],b [triangle]);Yang et al. (2008 [triangle]); Ejsmont et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o883-scheme1.jpg

Experimental

Crystal data

  • C16H15BrN2O3
  • M r = 363.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o883-efi1.jpg
  • a = 29.063 (3) Å
  • b = 10.934 (2) Å
  • c = 9.913 (2) Å
  • β = 96.77 (3)°
  • V = 3128.1 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.64 mm−1
  • T = 298 K
  • 0.35 × 0.33 × 0.30 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.458, T max = 0.505 (expected range = 0.411–0.453)
  • 25535 measured reflections
  • 6785 independent reflections
  • 3586 reflections with I > 2σ(I)
  • R int = 0.076

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.163
  • S = 1.03
  • 6785 reflections
  • 407 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.65 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010435/bx2199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010435/bx2199Isup2.hkl

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

Acknowledgments

Financial support of this work was provided by the Research Foundation of Liaoning Province (grant No. 2008470).

supplementary crystallographic information

Comment

Hydrazones derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a great deal of hydrazones have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported two hydrazones (Ban & Li, 2008a,b). In this paper, we report herein the crytal structure of the title new compound, (I).

In the structure of the title compound, Fig. 1, there are two independent molecules. Each molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angles between the two substituted benzene rings are 72.6 (2) and 18.8 (2)°, respectively. The torsion angles of C7-N1-N2-C8 and C22-N3-N4-C23 are 12.2 (3) and 4.6 (3)°, respectively. The molecular packing is stabilized by two intermolecular N-H···O hydrogen bond to form chains parallel to the c axis, Fig 2. Only the A molecules of the asymmetric unit are held together by π - π interactions [Cg···Cgi(-x+1, -y,-z+1) = 3.714 (3) Å; Cg is the centroid of the C1–C6 ring].

Experimental

The compound was prepared by refluxing 5-bromo-2-methoxybenzaldehyde (1.0 mol, 215.0 mg) with 3-methoxybenzohydrazide (1.0 mol, 166.2 mg) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colourless solid product was filtered, and washed three times with methanol. Colourless block crystals of the title compound were obtained from a methanol solution by slow evaporation in air.

Refinement

H2 and H4A were located in a difference Fourier map and refined isotropically, with N–H distances restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions (C–H = 0.93 - 0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl C). A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The molecular structure of (I), showing 30% probability displacement ellipsoids for the non-hydrogen atoms. The independent molecules are labelled as A and B.
Fig. 2.
The packing diagram of (I), viewed along the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C16H15BrN2O3F(000) = 1472
Mr = 363.21Dx = 1.542 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2210 reflections
a = 29.063 (3) Åθ = 2.4–25.0°
b = 10.934 (2) ŵ = 2.64 mm1
c = 9.913 (2) ÅT = 298 K
β = 96.77 (3)°Block, colourless
V = 3128.1 (9) Å30.35 × 0.33 × 0.30 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer6785 independent reflections
Radiation source: fine-focus sealed tube3586 reflections with I > 2σ(I)
graphiteRint = 0.076
ω scansθmax = 27.0°, θmin = 0.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −36→36
Tmin = 0.458, Tmax = 0.504k = −13→13
25535 measured reflectionsl = −12→12

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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0638P)2] where P = (Fo2 + 2Fc2)/3
6785 reflections(Δ/σ)max = 0.002
407 parametersΔρmax = 0.65 e Å3
2 restraintsΔρmin = −0.38 e Å3

Special details

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)

xyzUiso*/Ueq
Br10.438449 (17)−0.08256 (5)0.10000 (5)0.0545 (2)
Br21.065761 (17)0.43703 (5)0.40596 (5)0.0581 (2)
O10.58800 (11)−0.0965 (3)0.5745 (3)0.0532 (9)
O20.65071 (10)0.2123 (3)0.0643 (3)0.0447 (8)
O30.82081 (12)0.3545 (4)0.1065 (4)0.0733 (12)
O40.91879 (10)0.3807 (3)−0.0700 (3)0.0421 (8)
O50.85418 (11)0.7479 (3)0.4006 (3)0.0490 (9)
O60.68171 (11)0.8009 (4)0.0299 (4)0.0617 (11)
N10.60720 (11)0.1219 (3)0.2680 (4)0.0322 (9)
N20.64423 (12)0.2014 (3)0.2890 (3)0.0311 (9)
N30.89398 (11)0.6183 (3)0.2154 (3)0.0294 (8)
N40.85570 (11)0.6914 (3)0.1825 (3)0.0279 (8)
C10.55693 (15)−0.0144 (4)0.3641 (5)0.0336 (11)
C20.55304 (16)−0.0983 (4)0.4708 (5)0.0380 (11)
C30.51509 (16)−0.1751 (4)0.4633 (5)0.0439 (12)
H30.5126−0.23160.53220.053*
C40.48093 (16)−0.1689 (4)0.3547 (5)0.0461 (13)
H40.4551−0.21940.35160.055*
C50.48517 (16)−0.0880 (4)0.2512 (5)0.0400 (12)
C60.52270 (15)−0.0118 (4)0.2540 (5)0.0371 (11)
H60.52520.04160.18230.045*
C70.59695 (15)0.0686 (4)0.3739 (5)0.0346 (11)
H70.61460.08190.45710.042*
C80.66335 (14)0.2452 (4)0.1807 (4)0.0295 (10)
C90.70434 (15)0.3267 (4)0.2147 (4)0.0341 (11)
C100.74124 (15)0.3062 (4)0.1390 (4)0.0386 (11)
H100.73860.24890.06920.046*
C110.78178 (17)0.3722 (4)0.1689 (5)0.0487 (13)
C120.7840 (2)0.4613 (5)0.2699 (5)0.0573 (16)
H120.81110.50630.29030.069*
C130.7479 (2)0.4832 (5)0.3381 (6)0.0625 (16)
H130.74980.54440.40370.075*
C140.70764 (19)0.4158 (4)0.3121 (5)0.0522 (14)
H140.68280.43100.36090.063*
C150.82060 (19)0.2521 (6)0.0171 (6)0.0752 (19)
H15A0.81370.17910.06470.113*
H15B0.85050.2443−0.01420.113*
H15C0.79750.2641−0.05920.113*
C160.94706 (14)0.4789 (4)0.1332 (4)0.0285 (10)
C170.95361 (15)0.3906 (4)0.0343 (4)0.0320 (10)
C180.99351 (16)0.3197 (4)0.0470 (5)0.0398 (12)
H180.99770.2614−0.01880.048*
C191.02690 (15)0.3349 (4)0.1562 (5)0.0413 (12)
H191.05380.28800.16360.050*
C201.02034 (15)0.4200 (4)0.2547 (5)0.0391 (12)
C210.98093 (15)0.4919 (4)0.2430 (4)0.0347 (11)
H210.97710.54970.30960.042*
C220.90613 (14)0.5574 (4)0.1158 (4)0.0289 (10)
H220.88870.56300.03100.035*
C230.83808 (15)0.7528 (4)0.2815 (5)0.0324 (10)
C240.79532 (15)0.8269 (4)0.2384 (4)0.0319 (10)
C250.76058 (14)0.7787 (4)0.1458 (4)0.0377 (11)
H250.76500.70460.10310.045*
C260.71882 (16)0.8424 (5)0.1170 (5)0.0455 (13)
C270.71308 (19)0.9548 (5)0.1785 (6)0.0530 (14)
H270.68570.99860.15920.064*
C280.74795 (19)0.9991 (5)0.2667 (6)0.0619 (16)
H280.74421.07470.30690.074*
C290.78892 (19)0.9369 (4)0.2998 (5)0.0528 (14)
H290.81190.96920.36290.063*
C300.68602 (19)0.6876 (6)−0.0361 (6)0.0719 (18)
H30A0.71320.6888−0.08260.108*
H30B0.65920.6741−0.10050.108*
H30C0.68870.62300.03000.108*
C310.92295 (18)0.2885 (5)−0.1714 (5)0.0604 (16)
H31A0.94970.3053−0.21670.091*
H31B0.89570.2891−0.23630.091*
H31C0.92630.2097−0.12860.091*
C320.58764 (19)−0.1863 (5)0.6795 (5)0.0688 (17)
H32A0.5599−0.17740.72260.103*
H32B0.6142−0.17500.74550.103*
H32C0.5885−0.26660.64070.103*
H20.6553 (18)0.222 (5)0.374 (2)0.080*
H4A0.8453 (17)0.713 (5)0.097 (2)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0435 (3)0.0704 (4)0.0482 (4)−0.0108 (3)0.0001 (3)−0.0070 (3)
Br20.0421 (3)0.0750 (4)0.0537 (4)0.0093 (3)−0.0090 (3)0.0077 (3)
O10.048 (2)0.063 (2)0.048 (2)−0.0067 (18)−0.0005 (17)0.0185 (19)
O20.0447 (19)0.061 (2)0.0287 (19)−0.0067 (17)0.0045 (15)0.0080 (17)
O30.054 (2)0.085 (3)0.087 (3)−0.033 (2)0.035 (2)−0.022 (3)
O40.0378 (19)0.048 (2)0.041 (2)−0.0007 (16)0.0059 (15)−0.0140 (16)
O50.049 (2)0.066 (2)0.0299 (19)0.0205 (18)−0.0017 (16)−0.0133 (17)
O60.036 (2)0.082 (3)0.064 (3)0.0124 (19)−0.0072 (18)−0.001 (2)
N10.0269 (19)0.036 (2)0.034 (2)−0.0021 (17)0.0063 (17)0.0014 (18)
N20.029 (2)0.035 (2)0.030 (2)−0.0038 (17)0.0073 (17)0.0003 (18)
N30.0254 (19)0.032 (2)0.031 (2)0.0009 (16)0.0030 (16)−0.0021 (17)
N40.0250 (19)0.032 (2)0.027 (2)0.0053 (16)0.0045 (16)0.0020 (17)
C10.036 (3)0.034 (3)0.034 (3)−0.002 (2)0.013 (2)−0.004 (2)
C20.036 (3)0.037 (3)0.042 (3)−0.002 (2)0.010 (2)0.001 (2)
C30.047 (3)0.037 (3)0.050 (3)−0.006 (2)0.014 (3)0.009 (2)
C40.040 (3)0.043 (3)0.057 (4)−0.009 (2)0.014 (3)−0.008 (3)
C50.039 (3)0.047 (3)0.035 (3)−0.006 (2)0.010 (2)−0.007 (2)
C60.039 (3)0.036 (3)0.037 (3)−0.004 (2)0.010 (2)0.002 (2)
C70.036 (3)0.035 (3)0.033 (3)0.000 (2)0.006 (2)0.000 (2)
C80.026 (2)0.033 (3)0.030 (3)0.0083 (19)0.007 (2)0.008 (2)
C90.035 (3)0.033 (3)0.036 (3)−0.001 (2)0.010 (2)0.001 (2)
C100.043 (3)0.036 (3)0.039 (3)−0.004 (2)0.011 (2)0.004 (2)
C110.050 (3)0.048 (3)0.052 (3)−0.014 (3)0.020 (3)0.002 (3)
C120.080 (4)0.042 (3)0.054 (4)−0.030 (3)0.025 (3)−0.010 (3)
C130.085 (4)0.048 (4)0.060 (4)−0.023 (3)0.029 (3)−0.019 (3)
C140.067 (4)0.040 (3)0.054 (4)−0.009 (3)0.028 (3)−0.007 (3)
C150.053 (4)0.095 (5)0.086 (5)−0.009 (3)0.040 (3)−0.022 (4)
C160.032 (2)0.029 (2)0.026 (2)0.0022 (19)0.0094 (19)0.0029 (19)
C170.032 (3)0.035 (3)0.031 (3)−0.006 (2)0.010 (2)−0.002 (2)
C180.044 (3)0.032 (3)0.046 (3)0.005 (2)0.017 (2)−0.002 (2)
C190.034 (3)0.040 (3)0.051 (3)0.009 (2)0.010 (2)0.013 (3)
C200.033 (3)0.039 (3)0.045 (3)−0.001 (2)0.001 (2)0.015 (2)
C210.037 (3)0.035 (3)0.033 (3)0.000 (2)0.008 (2)0.002 (2)
C220.027 (2)0.033 (3)0.027 (2)−0.0007 (19)0.0032 (19)0.000 (2)
C230.036 (3)0.029 (3)0.032 (3)−0.002 (2)0.002 (2)0.000 (2)
C240.039 (3)0.029 (3)0.028 (3)0.002 (2)0.006 (2)0.002 (2)
C250.042 (3)0.035 (3)0.036 (3)0.011 (2)0.008 (2)−0.002 (2)
C260.041 (3)0.053 (3)0.044 (3)0.011 (3)0.011 (2)0.010 (3)
C270.055 (3)0.041 (3)0.063 (4)0.026 (3)0.009 (3)0.005 (3)
C280.071 (4)0.034 (3)0.080 (4)0.019 (3)0.006 (3)−0.005 (3)
C290.066 (4)0.041 (3)0.051 (3)0.012 (3)0.002 (3)−0.009 (3)
C300.049 (3)0.096 (5)0.068 (4)0.003 (3)−0.004 (3)−0.017 (4)
C310.060 (3)0.072 (4)0.051 (3)−0.002 (3)0.015 (3)−0.031 (3)
C320.071 (4)0.080 (4)0.053 (4)0.005 (3)0.001 (3)0.030 (3)

Geometric parameters (Å, °)

Br1—C51.901 (5)C12—H120.9300
Br2—C201.886 (5)C13—C141.381 (7)
O1—C21.358 (5)C13—H130.9300
O1—C321.431 (6)C14—H140.9300
O2—C81.223 (5)C15—H15A0.9600
O3—C111.369 (5)C15—H15B0.9600
O3—C151.426 (6)C15—H15C0.9600
O4—C171.363 (5)C16—C211.386 (6)
O4—C311.438 (5)C16—C171.405 (6)
O5—C231.219 (5)C16—C221.460 (6)
O6—C261.376 (6)C17—C181.388 (6)
O6—C301.414 (6)C18—C191.376 (6)
N1—C71.267 (5)C18—H180.9300
N1—N21.380 (5)C19—C201.378 (6)
N2—C81.353 (5)C19—H190.9300
N2—H20.90 (3)C20—C211.383 (6)
N3—C221.275 (5)C21—H210.9300
N3—N41.377 (4)C22—H220.9300
N4—C231.339 (5)C23—C241.503 (6)
N4—H4A0.90 (3)C24—C291.371 (6)
C1—C61.388 (6)C24—C251.386 (6)
C1—C21.414 (6)C25—C261.399 (6)
C1—C71.470 (6)C25—H250.9300
C2—C31.382 (6)C26—C271.391 (7)
C3—C41.377 (6)C27—C281.348 (7)
C3—H30.9300C27—H270.9300
C4—C51.372 (6)C28—C291.377 (7)
C4—H40.9300C28—H280.9300
C5—C61.370 (6)C29—H290.9300
C6—H60.9300C30—H30A0.9600
C7—H70.9300C30—H30B0.9600
C8—C91.494 (6)C30—H30C0.9600
C9—C141.367 (6)C31—H31A0.9600
C9—C101.397 (6)C31—H31B0.9600
C10—C111.384 (6)C31—H31C0.9600
C10—H100.9300C32—H32A0.9600
C11—C121.393 (7)C32—H32B0.9600
C12—C131.336 (7)C32—H32C0.9600
C2—O1—C32118.2 (4)C21—C16—C17118.5 (4)
C11—O3—C15116.7 (4)C21—C16—C22121.7 (4)
C17—O4—C31118.0 (4)C17—C16—C22119.8 (4)
C26—O6—C30118.2 (4)O4—C17—C18124.2 (4)
C7—N1—N2114.8 (4)O4—C17—C16115.8 (4)
C8—N2—N1119.3 (4)C18—C17—C16120.1 (4)
C8—N2—H2122 (4)C19—C18—C17120.5 (4)
N1—N2—H2119 (4)C19—C18—H18119.7
C22—N3—N4114.2 (3)C17—C18—H18119.7
C23—N4—N3119.1 (3)C18—C19—C20119.7 (4)
C23—N4—H4A117 (3)C18—C19—H19120.2
N3—N4—H4A123 (3)C20—C19—H19120.2
C6—C1—C2119.2 (4)C19—C20—C21120.5 (4)
C6—C1—C7121.8 (4)C19—C20—Br2119.2 (3)
C2—C1—C7119.0 (4)C21—C20—Br2120.4 (4)
O1—C2—C3124.8 (4)C20—C21—C16120.8 (4)
O1—C2—C1116.0 (4)C20—C21—H21119.6
C3—C2—C1119.2 (5)C16—C21—H21119.6
C4—C3—C2120.6 (5)N3—C22—C16120.8 (4)
C4—C3—H3119.7N3—C22—H22119.6
C2—C3—H3119.7C16—C22—H22119.6
C5—C4—C3119.8 (4)O5—C23—N4123.5 (4)
C5—C4—H4120.1O5—C23—C24120.6 (4)
C3—C4—H4120.1N4—C23—C24115.9 (4)
C6—C5—C4121.2 (4)C29—C24—C25120.1 (4)
C6—C5—Br1119.4 (4)C29—C24—C23119.9 (4)
C4—C5—Br1119.4 (4)C25—C24—C23119.8 (4)
C5—C6—C1119.9 (4)C24—C25—C26119.5 (4)
C5—C6—H6120.0C24—C25—H25120.2
C1—C6—H6120.0C26—C25—H25120.2
N1—C7—C1119.4 (4)O6—C26—C27116.1 (4)
N1—C7—H7120.3O6—C26—C25124.1 (5)
C1—C7—H7120.3C27—C26—C25119.8 (5)
O2—C8—N2122.6 (4)C28—C27—C26118.8 (5)
O2—C8—C9122.1 (4)C28—C27—H27120.6
N2—C8—C9115.0 (4)C26—C27—H27120.6
C14—C9—C10119.9 (4)C27—C28—C29122.7 (5)
C14—C9—C8124.9 (4)C27—C28—H28118.7
C10—C9—C8115.2 (4)C29—C28—H28118.7
C11—C10—C9119.3 (4)C24—C29—C28119.1 (5)
C11—C10—H10120.4C24—C29—H29120.4
C9—C10—H10120.4C28—C29—H29120.4
O3—C11—C10124.0 (5)O6—C30—H30A109.5
O3—C11—C12117.0 (5)O6—C30—H30B109.5
C10—C11—C12119.0 (5)H30A—C30—H30B109.5
C13—C12—C11121.0 (5)O6—C30—H30C109.5
C13—C12—H12119.5H30A—C30—H30C109.5
C11—C12—H12119.5H30B—C30—H30C109.5
C12—C13—C14120.6 (5)O4—C31—H31A109.5
C12—C13—H13119.7O4—C31—H31B109.5
C14—C13—H13119.7H31A—C31—H31B109.5
C9—C14—C13120.0 (5)O4—C31—H31C109.5
C9—C14—H14120.0H31A—C31—H31C109.5
C13—C14—H14120.0H31B—C31—H31C109.5
O3—C15—H15A109.5O1—C32—H32A109.5
O3—C15—H15B109.5O1—C32—H32B109.5
H15A—C15—H15B109.5H32A—C32—H32B109.5
O3—C15—H15C109.5O1—C32—H32C109.5
H15A—C15—H15C109.5H32A—C32—H32C109.5
H15B—C15—H15C109.5H32B—C32—H32C109.5
C7—N1—N2—C8167.8 (4)C12—C13—C14—C9−0.8 (9)
C22—N3—N4—C23175.4 (4)C31—O4—C17—C181.9 (6)
C32—O1—C2—C34.8 (7)C31—O4—C17—C16−177.7 (4)
C32—O1—C2—C1−175.0 (4)C21—C16—C17—O4179.0 (4)
C6—C1—C2—O1179.4 (4)C22—C16—C17—O4−3.4 (6)
C7—C1—C2—O1−1.3 (6)C21—C16—C17—C18−0.6 (6)
C6—C1—C2—C3−0.4 (7)C22—C16—C17—C18177.0 (4)
C7—C1—C2—C3178.9 (4)O4—C17—C18—C19−179.5 (4)
O1—C2—C3—C4179.0 (4)C16—C17—C18—C190.1 (7)
C1—C2—C3—C4−1.2 (7)C17—C18—C19—C200.9 (7)
C2—C3—C4—C51.8 (7)C18—C19—C20—C21−1.4 (7)
C3—C4—C5—C6−0.7 (7)C18—C19—C20—Br2178.5 (3)
C3—C4—C5—Br1178.7 (4)C19—C20—C21—C160.8 (7)
C4—C5—C6—C1−1.0 (7)Br2—C20—C21—C16−179.1 (3)
Br1—C5—C6—C1179.7 (3)C17—C16—C21—C200.2 (6)
C2—C1—C6—C51.5 (7)C22—C16—C21—C20−177.3 (4)
C7—C1—C6—C5−177.8 (4)N4—N3—C22—C16177.8 (3)
N2—N1—C7—C1177.6 (4)C21—C16—C22—N3−18.1 (6)
C6—C1—C7—N1−18.0 (6)C17—C16—C22—N3164.4 (4)
C2—C1—C7—N1162.7 (4)N3—N4—C23—O50.1 (6)
N1—N2—C8—O2−3.9 (6)N3—N4—C23—C24−177.8 (3)
N1—N2—C8—C9−177.8 (3)O5—C23—C24—C2938.0 (6)
O2—C8—C9—C14143.8 (5)N4—C23—C24—C29−144.0 (4)
N2—C8—C9—C14−42.3 (6)O5—C23—C24—C25−136.1 (5)
O2—C8—C9—C10−36.7 (6)N4—C23—C24—C2541.9 (6)
N2—C8—C9—C10137.2 (4)C29—C24—C25—C26−0.9 (7)
C14—C9—C10—C113.5 (7)C23—C24—C25—C26173.2 (4)
C8—C9—C10—C11−176.1 (4)C30—O6—C26—C27179.4 (5)
C15—O3—C11—C10−7.5 (8)C30—O6—C26—C25−0.7 (7)
C15—O3—C11—C12171.5 (5)C24—C25—C26—O6−178.0 (4)
C9—C10—C11—O3176.1 (4)C24—C25—C26—C271.8 (7)
C9—C10—C11—C12−2.8 (7)O6—C26—C27—C28178.8 (5)
O3—C11—C12—C13−178.7 (5)C25—C26—C27—C28−1.0 (8)
C10—C11—C12—C130.3 (8)C26—C27—C28—C29−0.8 (9)
C11—C12—C13—C141.5 (9)C25—C24—C29—C28−0.9 (7)
C10—C9—C14—C13−1.7 (8)C23—C24—C29—C28−174.9 (5)
C8—C9—C14—C13177.8 (5)C27—C28—C29—C241.7 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.90 (3)2.03 (3)2.872 (5)155 (5)
N4—H4A···O5ii0.90 (3)2.04 (3)2.868 (5)153 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2199).

References

  • Ban, H.-Y. & Li, C.-M. (2008a). Acta Cryst. E64, o2177. [PMC free article] [PubMed]
  • Ban, H.-Y. & Li, C.-M. (2008b). Acta Cryst. E64, o2260. [PMC free article] [PubMed]
  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128. [PMC free article] [PubMed]
  • Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008a). Acta Cryst. E64, o1594–o1595. [PMC free article] [PubMed]
  • Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008b). Acta Cryst. E64, o1707. [PMC free article] [PubMed]
  • Jimenez-Pulido, S. B., Linares-Ordonez, F. M., Martinez-Martos, J. M., Moreno-Carretero, M. N., Quiros-Olozabal, M. & Ramirez-Exposito, M. J. (2008). J. Inorg. Biochem.102, 1677–1683. [PubMed]
  • Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem.42, 425–429. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186. [PMC free article] [PubMed]
  • Yehye, W. A., Rahman, N. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1824. [PMC free article] [PubMed]
  • Zhong, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett.17, 3774–3777. [PubMed]

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