PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1275.
Published online 2008 June 19. doi:  10.1107/S1600536808017911
PMCID: PMC2961851

(E)-N′-(5-Bromo-2-methoxy­benzyl­idene)-4-chloro­benzohydrazide

Abstract

The title Schiff base compound, C15H12BrClN2O2, crystallizes with two independent mol­ecules in the asymmetric unit. The mol­ecules adopt an E configuration with respect to the C=N double bond. The dihedral angles between the benzene rings are 24.4 (2) and 9.4 (2)° in the two mol­ecules. The crystal structure is stabilized by inter­molecular N—H(...)O hydrogen bonds, forming chains running along the b axis.

Related literature

For general background, see: Ali et al. (2005 [triangle]); Arıcı et al. (2005 [triangle]); Hebbachi & Benali-Cherif (2005 [triangle]); Kurtoglu & Ispir (2007 [triangle]); Qi et al. (2007 [triangle]); Sallam (2007 [triangle]); Salmon et al. (2005 [triangle]); Sarı et al. (2006 [triangle]); Tuncel & Sari (2007 [triangle]). For related structures, see: Lin (2007 [triangle]); Tang (2007 [triangle], 2008 [triangle]); Yang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1275-scheme1.jpg

Experimental

Crystal data

  • C15H12BrClN2O2
  • M r = 367.63
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1275-efi1.jpg
  • a = 7.636 (3) Å
  • b = 9.837 (4) Å
  • c = 20.524 (8) Å
  • α = 82.045 (5)°
  • β = 83.660 (6)°
  • γ = 87.573 (5)°
  • V = 1516.9 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.89 mm−1
  • T = 298 (2) K
  • 0.20 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.596, T max = 0.624
  • 8876 measured reflections
  • 6405 independent reflections
  • 3536 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.141
  • S = 1.02
  • 6405 reflections
  • 387 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.64 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017911/sj2515sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017911/sj2515Isup2.hkl

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

Acknowledgments

The author acknowledges Huaihua University for a research grant.

supplementary crystallographic information

Comment

Schiff bases are very important ligands as they can readily form stable complexes with most metal ions (Tuncel & Sari, 2007; Sallam, 2007; Salmon et al., 2005; Ali et al., 2005; Arıcı et al., 2005; Hebbachi & Benali-Cherif, 2005; Sarı et al., 2006). Furthermore, Schiff bases and their metal complexes have excellent biological properties (Kurtoglu & Ispir, 2007; Qi et al., 2007). The author has proeviously reported the crystal structure of the Schiff base compound, isonicotinic acid [1-(3,5-dibromo-2-hydroxyphenyl)methylidene]hydrazide methanol solvate, which shows antibacterial activity (Lin, 2007). As a continuation of work on such compounds, I report herein the crystal structure of the new Schiff base compound, (I), Figure 1.

The two unique molecules of (I) adopt trans configurations about the C═N double bonds. The bond lengths and bond angles are within normal ranges and comparable to those observed in other similar Schiff bases (Tang, 2007, 2008; Yang et al., 2008). The C8–N1 and C23–N3 bond lengths are respectively 1.268 (4) and 1.281 (5) Å, indicating they are double bonds while the C9–N2 and C24–N4 distances are 1.352 (5) and 1.349 (5) Å respectively, indicating some degree of conjugation in the molecules. The dihedral angle between the C1—C6 and C10—C15 benzene rings is 24.4 (2) ° with a 9.4 (2) ° angle between the C16—C21 and C25—C30 rings. The crystal structure is stabilized by intermolecular N–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Figure 2).

Experimental

5-Bromo-2-methoxybenzaldehyde (21.5 mg, 0.1 mmol) and 4-chlorobenzohydrazide (17.0 mg, 0.1 mmol) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature for 5 min to give a colorless solution. Colorless needle-like crystals of (I) were obtained from this solution on standing.

Refinement

Atoms H2 attached to N2 and H4A attached to N4 were located in a difference Fourier map and refined isotropically, with N–H distances restrained to be 0.90 (1) Å. Other H atoms were placed in the calculated positions and constrained to ride on their parent atoms, with C–H distances in the range 0.93–0.96 Å, and with Uiso(H) values set to 1.2Ueq(C) and 1.5Ueq(methyl C). Crystals of (I) were small and very weakly diffracting reducing the amount of data collected.

Figures

Fig. 1.
The asymmetric unit of (I) with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
Molecular packing of (I) with hydrogen bonds drawn as dashed lines.

Crystal data

C15H12BrClN2O2Z = 4
Mr = 367.63F000 = 736
Triclinic, P1Dx = 1.610 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.636 (3) ÅCell parameters from 2115 reflections
b = 9.837 (4) Åθ = 2.4–24.5º
c = 20.524 (8) ŵ = 2.89 mm1
α = 82.045 (5)ºT = 298 (2) K
β = 83.660 (6)ºCut from a needle, colorless
γ = 87.573 (5)º0.20 × 0.20 × 0.18 mm
V = 1516.9 (10) Å3

Data collection

Bruker SMART APEX CCD area-detector diffractometer6405 independent reflections
Radiation source: fine-focus sealed tube3536 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 298(2) Kθmax = 27.0º
ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −9→8
Tmin = 0.596, Tmax = 0.624k = −12→12
8876 measured reflectionsl = −22→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141  w = 1/[σ2(Fo2) + (0.0616P)2 + 0.0769P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
6405 reflectionsΔρmax = 0.53 e Å3
387 parametersΔρmin = −0.64 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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*/Ueq
Br1−0.26007 (7)0.58987 (6)0.37080 (3)0.0799 (2)
Br20.70280 (8)−0.20259 (6)0.50498 (3)0.0802 (2)
Cl11.33371 (15)0.53500 (15)0.06070 (7)0.0791 (4)
Cl20.17724 (17)0.08183 (14)1.11711 (6)0.0720 (4)
O10.0684 (3)0.0824 (3)0.26908 (15)0.0538 (8)
O20.5295 (4)0.6554 (3)0.20845 (15)0.0540 (8)
O30.7291 (4)0.3334 (3)0.61136 (16)0.0647 (9)
O40.3751 (4)−0.1646 (3)0.83186 (14)0.0564 (8)
N10.3455 (4)0.4277 (3)0.24230 (16)0.0396 (8)
N20.5140 (4)0.4259 (3)0.21166 (16)0.0381 (8)
N30.5078 (4)0.0226 (3)0.73272 (16)0.0391 (8)
N40.4450 (4)0.0552 (3)0.79436 (15)0.0366 (7)
C10.0856 (5)0.3112 (4)0.28578 (18)0.0393 (9)
C2−0.0160 (5)0.1942 (4)0.29267 (19)0.0428 (10)
C3−0.1897 (5)0.1970 (5)0.3207 (2)0.0530 (11)
H3−0.25770.11980.32350.064*
C4−0.2615 (6)0.3127 (5)0.3442 (2)0.0562 (12)
H4−0.37730.31390.36370.067*
C5−0.1607 (6)0.4277 (4)0.3388 (2)0.0491 (11)
C60.0089 (5)0.4277 (4)0.3099 (2)0.0450 (10)
H60.07420.50660.30630.054*
C7−0.0205 (6)−0.0445 (4)0.2809 (3)0.0658 (14)
H7A−0.0422−0.07260.32770.099*
H7B0.0514−0.11320.26090.099*
H7C−0.1306−0.03310.26200.099*
C80.2686 (5)0.3138 (4)0.25389 (18)0.0386 (9)
H80.32610.23380.24260.046*
C90.5984 (5)0.5460 (4)0.19608 (19)0.0387 (9)
C100.7809 (5)0.5382 (4)0.16255 (19)0.0380 (9)
C110.8303 (6)0.4472 (4)0.1180 (2)0.0543 (12)
H110.74960.38550.10940.065*
C121.0006 (6)0.4474 (4)0.0860 (2)0.0619 (13)
H121.03310.38810.05490.074*
C131.1199 (5)0.5355 (4)0.1006 (2)0.0503 (11)
C141.0735 (6)0.6255 (4)0.1447 (2)0.0519 (11)
H141.15600.68480.15420.062*
C150.9042 (5)0.6280 (4)0.1750 (2)0.0470 (10)
H150.87180.69090.20440.056*
C160.6500 (5)0.1030 (4)0.62592 (19)0.0388 (9)
C170.7266 (5)0.2153 (4)0.5841 (2)0.0480 (10)
C180.7957 (6)0.1997 (5)0.5206 (2)0.0634 (13)
H180.84700.27380.49310.076*
C190.7896 (6)0.0768 (5)0.4976 (2)0.0650 (13)
H190.83630.06730.45460.078*
C200.7141 (5)−0.0335 (5)0.5381 (2)0.0530 (11)
C210.6451 (5)−0.0205 (4)0.6024 (2)0.0455 (10)
H210.5954−0.09570.62950.055*
C220.7650 (8)0.4582 (5)0.5692 (3)0.0902 (19)
H22A0.88280.45390.54770.135*
H22B0.75350.53320.59490.135*
H22C0.68290.47210.53650.135*
C230.5758 (5)0.1230 (4)0.69281 (19)0.0390 (9)
H230.57790.20910.70650.047*
C240.3841 (5)−0.0456 (4)0.8418 (2)0.0394 (9)
C250.3300 (5)−0.0040 (4)0.90879 (19)0.0356 (9)
C260.2364 (5)−0.0993 (4)0.9552 (2)0.0505 (11)
H260.2062−0.18200.94290.061*
C270.1892 (6)−0.0726 (5)1.0180 (2)0.0565 (12)
H270.1274−0.13691.04850.068*
C280.2331 (5)0.0499 (4)1.0362 (2)0.0463 (10)
C290.3231 (5)0.1459 (4)0.9917 (2)0.0514 (11)
H290.35190.22871.00440.062*
C300.3706 (5)0.1186 (4)0.9278 (2)0.0455 (10)
H300.43070.18380.89730.055*
H20.563 (5)0.345 (2)0.203 (2)0.080*
H4A0.440 (6)0.1421 (19)0.803 (2)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0826 (4)0.0853 (4)0.0695 (4)0.0282 (3)0.0066 (3)−0.0234 (3)
Br20.1092 (5)0.0691 (4)0.0665 (4)0.0134 (3)−0.0071 (3)−0.0312 (3)
Cl10.0522 (7)0.1017 (10)0.0773 (10)−0.0086 (7)0.0133 (6)−0.0042 (8)
Cl20.0843 (9)0.0966 (10)0.0361 (7)0.0092 (7)−0.0019 (6)−0.0191 (6)
O10.0520 (17)0.0475 (17)0.063 (2)−0.0136 (14)0.0019 (14)−0.0123 (15)
O20.0693 (19)0.0282 (15)0.062 (2)−0.0032 (14)0.0134 (15)−0.0118 (14)
O30.089 (2)0.0479 (19)0.053 (2)−0.0178 (16)−0.0013 (16)0.0053 (16)
O40.089 (2)0.0272 (15)0.0509 (19)−0.0125 (14)0.0168 (15)−0.0122 (13)
N10.0406 (19)0.0320 (18)0.045 (2)−0.0011 (14)0.0018 (15)−0.0057 (15)
N20.0409 (19)0.0267 (17)0.045 (2)−0.0022 (14)0.0031 (15)−0.0049 (15)
N30.0456 (19)0.0354 (17)0.0360 (19)−0.0010 (15)0.0004 (15)−0.0079 (15)
N40.0527 (19)0.0285 (16)0.0277 (18)−0.0052 (15)0.0038 (14)−0.0055 (15)
C10.044 (2)0.046 (2)0.026 (2)−0.0040 (19)0.0002 (17)−0.0007 (18)
C20.050 (2)0.049 (3)0.030 (2)−0.004 (2)−0.0038 (18)−0.0053 (19)
C30.047 (3)0.063 (3)0.046 (3)−0.014 (2)0.003 (2)−0.001 (2)
C40.043 (2)0.086 (4)0.037 (3)−0.001 (2)0.0058 (19)−0.005 (2)
C50.052 (3)0.060 (3)0.034 (2)0.010 (2)−0.0023 (19)−0.008 (2)
C60.049 (2)0.047 (2)0.038 (2)−0.0004 (19)−0.0029 (19)−0.005 (2)
C70.067 (3)0.048 (3)0.085 (4)−0.017 (2)−0.015 (3)−0.009 (3)
C80.048 (2)0.033 (2)0.035 (2)0.0020 (18)−0.0023 (18)−0.0068 (18)
C90.053 (2)0.030 (2)0.033 (2)−0.0063 (18)0.0004 (18)−0.0085 (17)
C100.049 (2)0.0258 (19)0.037 (2)−0.0038 (17)−0.0020 (18)0.0001 (17)
C110.058 (3)0.039 (2)0.066 (3)−0.015 (2)0.011 (2)−0.016 (2)
C120.070 (3)0.046 (3)0.068 (3)−0.009 (2)0.018 (2)−0.020 (2)
C130.050 (3)0.047 (3)0.049 (3)−0.005 (2)0.004 (2)0.007 (2)
C140.056 (3)0.053 (3)0.046 (3)−0.020 (2)−0.008 (2)0.002 (2)
C150.061 (3)0.041 (2)0.040 (3)−0.010 (2)−0.002 (2)−0.0085 (19)
C160.041 (2)0.043 (2)0.031 (2)−0.0017 (18)−0.0017 (17)−0.0009 (19)
C170.054 (3)0.043 (2)0.046 (3)−0.001 (2)−0.004 (2)−0.002 (2)
C180.072 (3)0.062 (3)0.047 (3)−0.002 (2)0.010 (2)0.011 (3)
C190.077 (3)0.074 (4)0.037 (3)0.007 (3)0.010 (2)−0.002 (3)
C200.055 (3)0.058 (3)0.046 (3)0.007 (2)−0.004 (2)−0.014 (2)
C210.049 (2)0.045 (2)0.042 (3)0.0040 (19)−0.0046 (19)−0.005 (2)
C220.129 (5)0.054 (3)0.085 (4)−0.028 (3)−0.029 (4)0.023 (3)
C230.045 (2)0.034 (2)0.039 (2)−0.0010 (18)−0.0025 (18)−0.0088 (19)
C240.042 (2)0.029 (2)0.047 (3)−0.0009 (17)−0.0016 (18)−0.0052 (19)
C250.039 (2)0.034 (2)0.034 (2)0.0023 (16)−0.0053 (17)−0.0058 (18)
C260.064 (3)0.036 (2)0.050 (3)−0.010 (2)0.006 (2)−0.006 (2)
C270.070 (3)0.050 (3)0.045 (3)−0.001 (2)0.007 (2)0.003 (2)
C280.053 (2)0.055 (3)0.030 (2)0.009 (2)−0.0051 (19)−0.007 (2)
C290.064 (3)0.043 (2)0.050 (3)−0.001 (2)−0.006 (2)−0.019 (2)
C300.064 (3)0.035 (2)0.036 (2)−0.0056 (19)0.0026 (19)−0.0056 (18)

Geometric parameters (Å, °)

Br1—C51.905 (4)C10—C151.386 (5)
Br2—C201.891 (5)C11—C121.390 (6)
Cl1—C131.744 (4)C11—H110.9300
Cl2—C281.736 (4)C12—C131.367 (6)
O1—C21.371 (5)C12—H120.9300
O1—C71.424 (5)C13—C141.362 (6)
O2—C91.224 (4)C14—C151.372 (6)
O3—C171.359 (5)C14—H140.9300
O3—C221.419 (5)C15—H150.9300
O4—C241.222 (4)C16—C211.372 (5)
N1—C81.268 (4)C16—C171.407 (5)
N1—N21.369 (4)C16—C231.462 (5)
N2—C91.352 (5)C17—C181.379 (6)
N2—H20.894 (10)C18—C191.361 (7)
N3—C231.281 (5)C18—H180.9300
N3—N41.378 (4)C19—C201.378 (6)
N4—C241.349 (5)C19—H190.9300
N4—H4A0.893 (10)C20—C211.385 (6)
C1—C61.393 (5)C21—H210.9300
C1—C21.397 (5)C22—H22A0.9600
C1—C81.475 (5)C22—H22B0.9600
C2—C31.387 (5)C22—H22C0.9600
C3—C41.367 (6)C23—H230.9300
C3—H30.9300C24—C251.498 (5)
C4—C51.380 (6)C25—C301.376 (5)
C4—H40.9300C25—C261.399 (5)
C5—C61.363 (5)C26—C271.356 (6)
C6—H60.9300C26—H260.9300
C7—H7A0.9600C27—C281.375 (6)
C7—H7B0.9600C27—H270.9300
C7—H7C0.9600C28—C291.370 (6)
C8—H80.9300C29—C301.382 (6)
C9—C101.488 (5)C29—H290.9300
C10—C111.378 (6)C30—H300.9300
C2—O1—C7118.0 (3)C13—C14—H14120.3
C17—O3—C22119.0 (4)C15—C14—H14120.3
C8—N1—N2116.5 (3)C14—C15—C10121.0 (4)
C9—N2—N1118.4 (3)C14—C15—H15119.5
C9—N2—H2123 (3)C10—C15—H15119.5
N1—N2—H2118 (3)C21—C16—C17119.1 (4)
C23—N3—N4114.4 (3)C21—C16—C23122.3 (4)
C24—N4—N3119.1 (3)C17—C16—C23118.6 (4)
C24—N4—H4A120 (3)O3—C17—C18124.6 (4)
N3—N4—H4A121 (3)O3—C17—C16115.6 (4)
C6—C1—C2118.0 (4)C18—C17—C16119.8 (4)
C6—C1—C8120.1 (3)C19—C18—C17120.7 (4)
C2—C1—C8122.0 (4)C19—C18—H18119.7
O1—C2—C3124.6 (4)C17—C18—H18119.7
O1—C2—C1115.0 (3)C18—C19—C20119.9 (5)
C3—C2—C1120.4 (4)C18—C19—H19120.1
C4—C3—C2120.4 (4)C20—C19—H19120.1
C4—C3—H3119.8C19—C20—C21120.5 (4)
C2—C3—H3119.8C19—C20—Br2119.4 (4)
C3—C4—C5119.5 (4)C21—C20—Br2120.1 (3)
C3—C4—H4120.3C16—C21—C20120.1 (4)
C5—C4—H4120.3C16—C21—H21119.9
C6—C5—C4120.9 (4)C20—C21—H21119.9
C6—C5—Br1119.3 (3)O3—C22—H22A109.5
C4—C5—Br1119.8 (3)O3—C22—H22B109.5
C5—C6—C1120.9 (4)H22A—C22—H22B109.5
C5—C6—H6119.6O3—C22—H22C109.5
C1—C6—H6119.6H22A—C22—H22C109.5
O1—C7—H7A109.5H22B—C22—H22C109.5
O1—C7—H7B109.5N3—C23—C16120.4 (4)
H7A—C7—H7B109.5N3—C23—H23119.8
O1—C7—H7C109.5C16—C23—H23119.8
H7A—C7—H7C109.5O4—C24—N4122.8 (4)
H7B—C7—H7C109.5O4—C24—C25121.2 (3)
N1—C8—C1118.4 (3)N4—C24—C25116.0 (3)
N1—C8—H8120.8C30—C25—C26118.5 (4)
C1—C8—H8120.8C30—C25—C24124.5 (3)
O2—C9—N2122.3 (4)C26—C25—C24117.0 (3)
O2—C9—C10121.5 (3)C27—C26—C25120.9 (4)
N2—C9—C10116.2 (3)C27—C26—H26119.6
C11—C10—C15118.8 (4)C25—C26—H26119.6
C11—C10—C9122.3 (3)C26—C27—C28119.7 (4)
C15—C10—C9118.9 (4)C26—C27—H27120.1
C10—C11—C12120.2 (4)C28—C27—H27120.1
C10—C11—H11119.9C29—C28—C27120.9 (4)
C12—C11—H11119.9C29—C28—Cl2119.6 (4)
C13—C12—C11119.5 (4)C27—C28—Cl2119.6 (3)
C13—C12—H12120.3C28—C29—C30119.3 (4)
C11—C12—H12120.3C28—C29—H29120.4
C14—C13—C12121.1 (4)C30—C29—H29120.4
C14—C13—Cl1119.4 (3)C25—C30—C29120.8 (4)
C12—C13—Cl1119.4 (4)C25—C30—H30119.6
C13—C14—C15119.5 (4)C29—C30—H30119.6

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O4i0.894 (10)2.026 (16)2.900 (4)165 (4)
N4—H4A···O2ii0.893 (10)1.994 (18)2.854 (4)161 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2515).

References

  • Ali, H. M., Kamalul Aripin, N. F. & Ng, S. W. (2005). Acta Cryst. E61, m433–m434.
  • Arıcı, C., Yüzer, D., Atakol, O., Fuess, H. & Svoboda, I. (2005). Acta Cryst. E61, m919–m921.
  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hebbachi, R. & Benali-Cherif, N. (2005). Acta Cryst. E61, m1188–m1190.
  • Kurtoglu, M. & Ispir, E. (2007). Asian J. Chem.19, 1239–1245.
  • Lin, H.-W. (2007). Chin. J. Struct. Chem.26, 773–776.
  • Qi, G.-F., Yang, Z.-Y. & Wang, B.-D. (2007). Transition Met. Chem.32, 233–239.
  • Sallam, S. A. (2007). J. Coord. Chem.60, 951–971.
  • Salmon, L., Thuéry, P. & Ephritikhine, M. (2005). Acta Cryst. E61, m2607–m2609.
  • Sarı, M., Atakol, O., Svoboda, I. & Fuess, H. (2006). Acta Cryst. E62, m563–m565.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tang, C.-B. (2007). Acta Cryst. E63, o4545.
  • Tang, C.-B. (2008). Acta Cryst. E64, o767. [PMC free article] [PubMed]
  • Tuncel, M. & Sari, H. (2007). Transition Met. Chem.32, 803–810.
  • Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186. [PMC free article] [PubMed]

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