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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 3| March 2011| Pages o657-o658

2-[1-(3-{2-[(2-Hy­dr­oxy­benzyl­­idene)amino]­phen­­oxy}prop­yl)-1H-1,3-benzo­diazol-2-yl]phenol

aFaculty of Chemistry, Bu-Ali Sina University, Hamedan 65174, Iran, bDepartment of Chemistry, Alzahra University, Vanak, Tehran, Iran, cDepartment of Chemistry, Payam Noor University, Hamedan, Iran, and dDepartment of Chemistry, Islamic Azad University, Buinzahra Branch, Buinzahra, Qazvin, Iran
*Correspondence e-mail: haskey1@yahoo.com

(Received 30 January 2011; accepted 12 February 2011; online 19 February 2011)

In the title compound, C29H25N3O3, the imine double bond has an E configuration. The dihedral angle between the hy­droxy­phenyl and benzene rings in the imine moiety is 26.95 (9)°, and the dihedral angle between the hy­droxy­phenyl and benzimidazole rings in the other moiety is 14.83 (9)°. These angles are probably limited to small values as a consequence of two strong intra­molecular O—H⋯N hydrogen bonds formed between the hy­droxy groups and the imine and imidazole N atoms. The aliphatic chain linking the two ring systems has a gauche conformation, as reflected in C—C—C—O torsion angle of 70.9 (2)°.

Related literature

For related structures, see: Keypour et al. (2009[Keypour, H., Azadbakht, R., Salehzadeh, S., Rudbari, H. A. & Adams, H. (2009). Tetrahedron Lett. 50, 169-171.]). For background information on diimine complexes, see: Mahmoudi et al. (2009[Mahmoudi, A., Dehghanpour, S., Khalaj, M. & Pakravan, S. (2009). Acta Cryst. E65, m889.]).

[Scheme 1]

Experimental

Crystal data
  • C29H25N3O3

  • Mr = 463.52

  • Monoclinic, P 21 /c

  • a = 9.1097 (6) Å

  • b = 18.1946 (11) Å

  • c = 13.7769 (5) Å

  • β = 93.405 (4)°

  • V = 2279.5 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 150 K

  • 0.25 × 0.12 × 0.10 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.866, Tmax = 0.993

  • 16359 measured reflections

  • 5135 independent reflections

  • 3083 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.137

  • S = 1.06

  • 5135 reflections

  • 318 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1O⋯N2 0.84 1.81 2.564 (2) 148
O3—H2O⋯N3 0.84 1.80 2.548 (2) 148

Data collection: COLLECT (Nonius, 2002[Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In our ongoing studies on the synthesis, structural and spectroscopic characterization of the products derived from N1-(3-(2-aminophenoxy)propyl)-benzene-1,2-diamine with aldehydes (Keypour et al., 2009; Mahmoudi et al., 2009) we report herein the crystal structure of the title compound, prepared by the reaction of N1-(3-(2-aminophenoxy)propyl)-benzene-1,2-diamine with salicyl aldehyde.

The molecular structure of the title compound is shown in Fig. 1. The molecule adopts the E configuration with respect to the imine CN bond. Two hydroxyl groups are located close to N atoms, and form strong intramolecular hydrogen bonds (Table 1).

Related literature top

For related structures, see: Keypour et al. (2009). For background information on diimine complexes, see: Mahmoudi et al. (2009).

Experimental top

N1-(3-(2-aminophenoxy)propyl)benzene-1,2-diamine (0.064 g, 0.25 mmol) in methanol (20 ml) was added dropwise with stirring to a solution of salicylaldehyde (0.061 g, 0.5 mmol) in methanol (30 ml). The mixture was refluxed for 12 h. Then, the solution volume was reduced to 10 ml by evaporation, and a precipitate was formed. This was filtered off, washed with ether, and dried in vacuo. Vapour diffusion of diethyl ether into a methanolic solution of the product afforded yellow crystals in 60% yield.

Refinement top

All C-bonded H atoms positions were calculated and refined with a riding model and Uiso(H) parameters set to 1.2 times Ueq(carrier C atom). Hydroxyl H atoms also ride on their O atoms, with O—H bond lengths fixed to 0.84 Å and Uiso(H) = 1.5 Ueq(carrier O atom).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the structure of the title complex, with displacement ellipsoids drawn at the 50% probability level.
2-[1-(3-{2-[(2-Hydroxybenzylidene)amino]phenoxy}propyl)-1H- 1,3-benzodiazol-2-yl]phenol top
Crystal data top
C29H25N3O3F(000) = 976
Mr = 463.52Dx = 1.351 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 16359 reflections
a = 9.1097 (6) Åθ = 2.7–27.5°
b = 18.1946 (11) ŵ = 0.09 mm1
c = 13.7769 (5) ÅT = 150 K
β = 93.405 (4)°Needle, yellow
V = 2279.5 (2) Å30.25 × 0.12 × 0.10 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
5135 independent reflections
Radiation source: fine-focus sealed tube3083 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 2.7°
ϕ scans and ω scans with κ offsetsh = 1111
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 2223
Tmin = 0.866, Tmax = 0.993l = 1717
16359 measured reflections
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0536P)2 + 0.4485P]
where P = (Fo2 + 2Fc2)/3
5135 reflections(Δ/σ)max = 0.001
318 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.20 e Å3
0 constraints
Crystal data top
C29H25N3O3V = 2279.5 (2) Å3
Mr = 463.52Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.1097 (6) ŵ = 0.09 mm1
b = 18.1946 (11) ÅT = 150 K
c = 13.7769 (5) Å0.25 × 0.12 × 0.10 mm
β = 93.405 (4)°
Data collection top
Nonius KappaCCD
diffractometer
5135 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
3083 reflections with I > 2σ(I)
Tmin = 0.866, Tmax = 0.993Rint = 0.054
16359 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0551 restraint
wR(F2) = 0.137H-atom parameters constrained
S = 1.06Δρmax = 0.23 e Å3
5135 reflectionsΔρmin = 0.20 e Å3
318 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.98262 (18)0.22668 (8)0.88875 (9)0.0465 (4)
H1O0.92120.19220.88640.070*
O20.80830 (16)0.02045 (7)0.35975 (9)0.0369 (4)
O30.69646 (17)0.13681 (8)0.49252 (9)0.0418 (4)
H2O0.72120.11560.44180.063*
N10.82575 (18)0.08636 (9)0.66217 (11)0.0352 (4)
N20.80517 (19)0.13040 (9)0.81279 (11)0.0378 (4)
N30.70199 (18)0.10938 (9)0.31140 (11)0.0323 (4)
C10.8674 (2)0.13987 (11)0.72906 (13)0.0348 (5)
C20.7258 (2)0.04118 (11)0.70695 (14)0.0355 (5)
C30.6454 (2)0.01894 (12)0.67220 (16)0.0424 (5)
H3A0.65270.03690.60790.051*
C40.5538 (2)0.05139 (12)0.73642 (17)0.0461 (6)
H4A0.49610.09260.71550.055*
C50.5439 (2)0.02520 (12)0.83139 (17)0.0462 (6)
H5A0.48050.04920.87360.055*
C60.6241 (2)0.03446 (12)0.86451 (16)0.0428 (5)
H6A0.61730.05200.92900.051*
C70.7156 (2)0.06849 (11)0.80071 (14)0.0371 (5)
C80.9683 (2)0.20146 (11)0.71522 (14)0.0342 (5)
C91.0249 (2)0.24102 (12)0.79778 (14)0.0358 (5)
C101.1272 (2)0.29677 (12)0.78825 (15)0.0406 (5)
H10A1.16820.32110.84450.049*
C111.1694 (2)0.31703 (12)0.69784 (16)0.0433 (5)
H11A1.24020.35490.69200.052*
C121.1092 (2)0.28247 (12)0.61553 (15)0.0411 (5)
H12A1.13530.29790.55300.049*
C131.0116 (2)0.22574 (11)0.62434 (14)0.0375 (5)
H13A0.97200.20210.56710.045*
C140.8752 (2)0.07122 (11)0.56509 (13)0.0354 (5)
H14A0.87710.01740.55450.042*
H14B0.97650.09000.56070.042*
C150.7747 (2)0.10687 (12)0.48571 (13)0.0372 (5)
H15A0.67490.08560.48770.045*
H15B0.76750.16020.49910.045*
C160.8287 (2)0.09626 (11)0.38527 (14)0.0375 (5)
H16A0.77250.12800.33800.045*
H16B0.93410.10950.38470.045*
C170.8190 (2)0.00152 (11)0.26392 (13)0.0319 (5)
C180.8766 (2)0.04669 (12)0.19473 (14)0.0382 (5)
H18A0.91540.09360.21270.046*
C190.8774 (2)0.02298 (12)0.09868 (15)0.0420 (5)
H19A0.91560.05420.05100.050*
C200.8233 (2)0.04524 (12)0.07220 (14)0.0408 (5)
H20A0.82490.06110.00660.049*
C210.7667 (2)0.09051 (12)0.14125 (14)0.0367 (5)
H21A0.73110.13790.12300.044*
C220.7614 (2)0.06751 (11)0.23715 (13)0.0320 (5)
C230.5987 (2)0.15625 (11)0.29380 (14)0.0344 (5)
H23A0.56040.16340.22880.041*
C240.5396 (2)0.19841 (11)0.37172 (14)0.0339 (5)
C250.4292 (2)0.25061 (12)0.35230 (16)0.0403 (5)
H25A0.39300.25840.28700.048*
C260.3717 (2)0.29106 (12)0.42569 (17)0.0458 (6)
H26A0.29650.32630.41140.055*
C270.4258 (2)0.27940 (12)0.52143 (16)0.0444 (6)
H27A0.38750.30730.57250.053*
C280.5338 (2)0.22813 (12)0.54275 (15)0.0407 (5)
H28A0.56870.22060.60830.049*
C290.5923 (2)0.18717 (11)0.46906 (14)0.0340 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0556 (11)0.0529 (11)0.0310 (8)0.0016 (8)0.0015 (7)0.0072 (7)
O20.0491 (9)0.0346 (8)0.0271 (7)0.0053 (7)0.0029 (6)0.0018 (6)
O30.0502 (10)0.0431 (9)0.0320 (8)0.0091 (7)0.0014 (6)0.0014 (6)
N10.0373 (10)0.0394 (10)0.0289 (9)0.0047 (8)0.0017 (7)0.0045 (7)
N20.0435 (11)0.0402 (11)0.0298 (9)0.0039 (9)0.0032 (7)0.0015 (7)
N30.0351 (10)0.0305 (10)0.0314 (9)0.0023 (8)0.0033 (7)0.0000 (7)
C10.0339 (12)0.0397 (13)0.0307 (11)0.0079 (9)0.0001 (8)0.0026 (9)
C20.0312 (12)0.0353 (12)0.0401 (12)0.0057 (9)0.0023 (9)0.0017 (9)
C30.0427 (13)0.0416 (14)0.0423 (13)0.0072 (11)0.0021 (10)0.0059 (10)
C40.0393 (14)0.0382 (13)0.0604 (15)0.0013 (11)0.0010 (11)0.0007 (11)
C50.0420 (14)0.0399 (14)0.0577 (15)0.0057 (11)0.0120 (11)0.0111 (11)
C60.0461 (14)0.0430 (14)0.0398 (12)0.0082 (11)0.0076 (10)0.0045 (10)
C70.0366 (12)0.0392 (13)0.0354 (12)0.0060 (10)0.0017 (9)0.0001 (9)
C80.0298 (11)0.0366 (12)0.0358 (11)0.0035 (9)0.0005 (8)0.0022 (9)
C90.0358 (12)0.0432 (13)0.0283 (11)0.0114 (10)0.0000 (8)0.0022 (9)
C100.0368 (13)0.0430 (13)0.0410 (13)0.0051 (11)0.0046 (9)0.0104 (10)
C110.0356 (13)0.0408 (13)0.0533 (14)0.0008 (10)0.0021 (10)0.0037 (10)
C120.0413 (13)0.0444 (14)0.0380 (12)0.0029 (11)0.0062 (9)0.0009 (10)
C130.0387 (13)0.0415 (13)0.0321 (11)0.0024 (10)0.0001 (9)0.0048 (9)
C140.0390 (12)0.0399 (12)0.0275 (11)0.0067 (10)0.0041 (8)0.0067 (9)
C150.0392 (12)0.0392 (13)0.0327 (11)0.0039 (10)0.0007 (9)0.0045 (9)
C160.0437 (13)0.0349 (12)0.0335 (11)0.0050 (10)0.0003 (9)0.0007 (9)
C170.0323 (11)0.0390 (12)0.0244 (10)0.0016 (9)0.0011 (8)0.0013 (8)
C180.0417 (13)0.0408 (13)0.0325 (12)0.0043 (10)0.0051 (9)0.0012 (9)
C190.0448 (14)0.0487 (14)0.0334 (12)0.0011 (11)0.0102 (9)0.0040 (10)
C200.0458 (14)0.0488 (14)0.0286 (11)0.0046 (11)0.0080 (9)0.0028 (9)
C210.0398 (13)0.0366 (13)0.0336 (11)0.0047 (10)0.0024 (9)0.0041 (9)
C220.0308 (11)0.0342 (12)0.0310 (11)0.0050 (9)0.0027 (8)0.0025 (8)
C230.0376 (12)0.0333 (12)0.0322 (11)0.0058 (10)0.0019 (9)0.0013 (9)
C240.0346 (12)0.0297 (11)0.0377 (12)0.0050 (9)0.0040 (9)0.0009 (9)
C250.0384 (13)0.0353 (12)0.0471 (13)0.0004 (10)0.0025 (10)0.0056 (10)
C260.0382 (14)0.0345 (13)0.0649 (16)0.0034 (10)0.0058 (11)0.0011 (11)
C270.0413 (14)0.0381 (13)0.0549 (14)0.0044 (11)0.0116 (10)0.0133 (10)
C280.0406 (13)0.0407 (13)0.0414 (12)0.0051 (11)0.0061 (9)0.0085 (10)
C290.0330 (12)0.0295 (12)0.0397 (12)0.0026 (9)0.0043 (9)0.0005 (9)
Geometric parameters (Å, º) top
O1—C91.358 (2)C12—H12A0.9500
O1—H1O0.8400C13—H13A0.9500
O2—C171.373 (2)C14—C151.528 (3)
O2—C161.433 (2)C14—H14A0.9900
O3—C291.344 (2)C14—H14B0.9900
O3—H2O0.8400C15—C161.508 (3)
N1—C11.378 (2)C15—H15A0.9900
N1—C21.397 (3)C15—H15B0.9900
N1—C141.462 (2)C16—H16A0.9900
N2—C11.326 (2)C16—H16B0.9900
N2—C71.395 (3)C17—C181.385 (3)
N3—C231.282 (2)C17—C221.402 (3)
N3—C221.409 (2)C18—C191.392 (3)
C1—C81.469 (3)C18—H18A0.9500
C2—C31.386 (3)C19—C201.377 (3)
C2—C71.392 (3)C19—H19A0.9500
C3—C41.384 (3)C20—C211.381 (3)
C3—H3A0.9500C20—H20A0.9500
C4—C51.400 (3)C21—C221.390 (3)
C4—H4A0.9500C21—H21A0.9500
C5—C61.371 (3)C23—C241.449 (3)
C5—H5A0.9500C23—H23A0.9500
C6—C71.392 (3)C24—C251.397 (3)
C6—H6A0.9500C24—C291.412 (3)
C8—C131.406 (3)C25—C261.379 (3)
C8—C91.417 (3)C25—H25A0.9500
C9—C101.388 (3)C26—C271.397 (3)
C10—C111.376 (3)C26—H26A0.9500
C10—H10A0.9500C27—C281.374 (3)
C11—C121.381 (3)C27—H27A0.9500
C11—H11A0.9500C28—C291.391 (3)
C12—C131.372 (3)C28—H28A0.9500
C9—O1—H1O109.5H14A—C14—H14B107.9
C17—O2—C16117.50 (14)C16—C15—C14112.85 (17)
C29—O3—H2O109.5C16—C15—H15A109.0
C1—N1—C2106.32 (16)C14—C15—H15A109.0
C1—N1—C14131.09 (17)C16—C15—H15B109.0
C2—N1—C14122.48 (16)C14—C15—H15B109.0
C1—N2—C7106.17 (16)H15A—C15—H15B107.8
C23—N3—C22122.11 (16)O2—C16—C15107.68 (16)
N2—C1—N1112.02 (18)O2—C16—H16A110.2
N2—C1—C8121.00 (17)C15—C16—H16A110.2
N1—C1—C8126.98 (18)O2—C16—H16B110.2
C3—C2—C7122.6 (2)C15—C16—H16B110.2
C3—C2—N1131.05 (19)H16A—C16—H16B108.5
C7—C2—N1106.32 (18)O2—C17—C18124.33 (18)
C4—C3—C2116.2 (2)O2—C17—C22115.51 (17)
C4—C3—H3A121.9C18—C17—C22120.12 (17)
C2—C3—H3A121.9C17—C18—C19119.6 (2)
C3—C4—C5121.8 (2)C17—C18—H18A120.2
C3—C4—H4A119.1C19—C18—H18A120.2
C5—C4—H4A119.1C20—C19—C18120.6 (2)
C6—C5—C4121.2 (2)C20—C19—H19A119.7
C6—C5—H5A119.4C18—C19—H19A119.7
C4—C5—H5A119.4C19—C20—C21119.83 (19)
C5—C6—C7118.0 (2)C19—C20—H20A120.1
C5—C6—H6A121.0C21—C20—H20A120.1
C7—C6—H6A121.0C20—C21—C22120.7 (2)
C6—C7—C2120.2 (2)C20—C21—H21A119.6
C6—C7—N2130.68 (19)C22—C21—H21A119.6
C2—C7—N2109.13 (17)C21—C22—C17119.08 (18)
C13—C8—C9116.56 (19)C21—C22—N3124.35 (18)
C13—C8—C1124.48 (18)C17—C22—N3116.57 (16)
C9—C8—C1118.95 (18)N3—C23—C24120.85 (18)
O1—C9—C10117.15 (18)N3—C23—H23A119.6
O1—C9—C8122.22 (19)C24—C23—H23A119.6
C10—C9—C8120.63 (18)C25—C24—C29118.71 (18)
C11—C10—C9120.45 (19)C25—C24—C23120.85 (18)
C11—C10—H10A119.8C29—C24—C23120.43 (18)
C9—C10—H10A119.8C26—C25—C24121.5 (2)
C10—C11—C12120.2 (2)C26—C25—H25A119.2
C10—C11—H11A119.9C24—C25—H25A119.2
C12—C11—H11A119.9C25—C26—C27118.9 (2)
C13—C12—C11119.8 (2)C25—C26—H26A120.6
C13—C12—H12A120.1C27—C26—H26A120.6
C11—C12—H12A120.1C28—C27—C26120.9 (2)
C12—C13—C8122.18 (18)C28—C27—H27A119.6
C12—C13—H13A118.9C26—C27—H27A119.6
C8—C13—H13A118.9C27—C28—C29120.5 (2)
N1—C14—C15111.78 (16)C27—C28—H28A119.7
N1—C14—H14A109.3C29—C28—H28A119.7
C15—C14—H14A109.3O3—C29—C28119.03 (18)
N1—C14—H14B109.3O3—C29—C24121.48 (18)
C15—C14—H14B109.3C28—C29—C24119.48 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N20.841.812.564 (2)148
O3—H2O···N30.841.802.548 (2)148

Experimental details

Crystal data
Chemical formulaC29H25N3O3
Mr463.52
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)9.1097 (6), 18.1946 (11), 13.7769 (5)
β (°) 93.405 (4)
V3)2279.5 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.12 × 0.10
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.866, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
16359, 5135, 3083
Rint0.054
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.137, 1.06
No. of reflections5135
No. of parameters318
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.20

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N20.841.812.564 (2)148
O3—H2O···N30.841.802.548 (2)148
 

Acknowledgements

We are grateful to Bu-Ali Sina and Alzahra Universities for financial support.

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationKeypour, H., Azadbakht, R., Salehzadeh, S., Rudbari, H. A. & Adams, H. (2009). Tetrahedron Lett. 50, 169–171.  Web of Science CSD CrossRef CAS Google Scholar
First citationMahmoudi, A., Dehghanpour, S., Khalaj, M. & Pakravan, S. (2009). Acta Cryst. E65, m889.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 3| March 2011| Pages o657-o658
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds