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

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ISSN: 2056-9890

N,N′-Bis(di­phenyl­meth­yl)benzene-1,4-di­amine

aDepartment of Chemistry, College of Science, University of Babylon, Iraq, bDepartment of Chemical Engineering and Chemical Technology, Imperial College London, London SW7 2AZ, England, cUK National Crystallography Service, Chemistry, Faculty of Natural and Environmental Sciences, University of Southampton, Southampton, SO17 1BJ, England, dDiamond Light Source, Harwell Science and Innovation Campus, Didcot, Oxfordshire OX11 0DE, England, and eSchool of Research, Enterprise and Innovation, Manchester Metropolitan University, Chester Street, Manchester M1 5GD, England
*Correspondence e-mail: aeedchemistry@yahoo.co.uk

(Received 4 November 2013; accepted 10 December 2013; online 14 December 2013)

The complete mol­ecule of the title compound, C32H28N2, is generated by crystallographic inversion symmetry. The dihedral angles between the central aromatic ring and the pendant adjacent rings are 61.37 (16) and 74.20 (14)°. The N—H group does not participate in hydrogen bonds and there are no aromatic ππ stacking inter­actions in the crystal.

Related literature

The reduction of the Schiff-base was as described in Higuchi et al. (2003[Higuchi, M., Tsuruta, M., Chiba, H., Shiki, S. & Yamamoto, K. (2003). J. Am. Chem. Soc. 125, 9988-9997.]) and Higuchi et al. (2000[Higuchi, M., Shiki, S. & Yamamoto, K. (2000). Org. Lett. 2, 3079-3082.]). For the use of dendrimers in the formation of new types of organic-metallic hybrid materials, see: Kim et al. (2005[Kim, Y.-G., Garcia-Martines, J. C. & Crooks, R. M. (2005). Langmuir, 21, 5485-5491.]); for drug generation, see: Basavaraj et al. (2009[Basavaraj, B. V., Furtado, F., Bharath, S., Deveswaran, R., Sindhu, A. & Madhavan, V. (2009). J. Pharm. Res, 2, 970-974.]). For related structures, see: Ge & Ng (2006[Ge, W.-Z. & Ng, S. W. (2006). Acta Cryst. E62, o3784-o3785.]); Yang et al. (2007[Yang, S.-P., Li-Jun, H., Da-Qi, W. & Tie-Zhu, D. (2007). Acta Cryst. E63, o244-o246.]); Xia et al. (2007[Xia, H.-T., Liu, Y.-F., Yang, S.-P. & Wang, D.-Q. (2007). Acta Cryst. E63, o40-o41.]). Data were collected and processed according to Coles & Gale (2012[Coles, S. J. & Gale, P. A. (2012). Chem. Sci. 3, 683-689.]).

[Scheme 1]

Experimental

Crystal data
  • C32H28N2

  • Mr = 440.56

  • Monoclinic, P 21 /n

  • a = 14.784 (2) Å

  • b = 5.5853 (8) Å

  • c = 14.896 (2) Å

  • β = 107.914 (8)°

  • V = 1170.4 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.1 × 0.09 × 0.02 mm

Data collection
  • Rigaku AFC12 (Right) diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Americas Corporation, The Woodlands, Texas, USA.]) Tmin = 0.345, Tmax = 1.000

  • 10305 measured reflections

  • 2664 independent reflections

  • 1254 reflections with I > 2σ(I)

  • Rint = 0.125

Refinement
  • R[F2 > 2σ(F2)] = 0.077

  • wR(F2) = 0.208

  • S = 0.97

  • 2664 reflections

  • 155 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.29 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Americas Corporation, The Woodlands, Texas, USA.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXD (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

Bis-amine compounds are essential building blocks to produce branched or dendritic polymers. Dendrimers are an interesting class of materials which are based on bis-aromatic imine and amine precursors. These polymeric materials have attracted increasing attention due to their functional coordination groups, which can trap many metal ions or metal clusters within the voids in the dendrimers. This can lead to the formation of new types of organic-metallic hybrid nanomaterials (Kim et al., 2005). Furthermore, the polyvalent nature of dendrimers is a key factor in generating a new class of drugs with much improved and acceptable pharmacokinetic profiles (Basavaraj et al., 2009). This paper reports on a new addition to the bis-amine compounds and its chemical and physical features.

The compound, with a molar mass of 440.56 g mol-1, crystallizes in a monoclinic crystal structure with a space group notation of P21/n and had a calculated density of 1.250 g cm-3. The asymmetric unit consists of half the molecule, the molecule is completed by inversion symmetry. Infrared spectra indicates typical absorbance bands of the functional phenyl group and amine –C=N group at 1570 and 1620 cm-1, respectively. The positive ES mass spectrum of the bis-amine showed a parent ion peak at m/z = 441.2362 (M+H)+, corresponding to C32H28N2, for which the required value = 440.2252.

Related literature top

The reduction of the Schiff-base was as described in Higuchi et al. (2003) and Higuchi et al. (2000). For the use of dendrimers in the formation of new types of organic-metallic hybrid materials, see: Kim et al. (2005); for drug generation, see: Basavaraj et al. (2009). For related structures, see: Ge & Ng (2006); Yang et al. (2007); Xia et al. (2007). Data were collected and processed according to Coles & Gale (2012).

Experimental top

The bis-amine {N1,N4-dibenzhydrylbenzene-1,4-diamine} was prepared in a two-step procedure as follows: (i) A Schiff-base {N1,N4-bis-(diphenylmethylene)benzene-1,4-diamine} was synthesized by adopting a conventional procedure (Higuchi et al., 2000) as follows: A mixture of benzophenone (1.69 g, 9.25 mmol), p-phenylenediamine (0.500 g, 4.62 mmol), and 1,4-diaza-bicyclo-[2.2.2]octane (DABCO) (3.11 g, 27.7 mmol) in chlorobenzene (40 ml) was stirred at room temperature for 10 min. Titanium (IV) tetrachloride (1.32 g, 6.93 mmol) dissolved in chlorobenzene (10 ml) was added dropwise using a pressure-equalized dropping funnel. The reaction mixture was heated in an oil bath at 125 °C for 24 h. The precipitate was removed by filtration, and then the filtrate was concentrated. The Schiff-base product (yield: 1.83 g, 91%) was isolated by silica gel uniplate chromatography with an eluent mixture of hexane:ethylacetate; 9:1, Rf = 0.25. (ii)The reduction of the Schiff-base was achieved using conventional procedures (Higuchi et al., 2000; 2003) as follows: NaBH4 (0.06 g, 1.74 mmol) was added cautiously and in small portions to a mixture of the Schiff-base {N1,N4-bis-(diphenylmethyene)benzene-1,4-diamine} (0.500 g, 0.437 mmol), and SnCl2 (0.17 g, 0.87 mmol) dissolved in a mixture of dichloromethane/acetonitrile (1:1) (200 ml). The reaction mixture was stirred at room temperature for 10 min under an Argon atmosphere. The crude mixture was washed with an aqueous solution of 1% triethylamine (4x100), and the organic layer was dried over Na2SO4. The secondary bis-amine was purified from the crude product by uniplate silica gel chromatography with eluent (hexane: acetonitrile: chloroform; 8: 2: 1), Rf = 0.5. Yield: 0.98 g, 54.14%. Colourless plates were obtained from slow evaporation of a methanol solution of the bis-amine in air.

Refinement top

Data were collected and processed according to Coles & Gale (2012). Hydrogen atoms were placed in geometrically calculated positions and included as part of a riding model with Uiso values set at 1.2 times Ueq of the parent atom.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell refinement: CrystalClear-SM Expert (Rigaku, 2012); data reduction: CrystalClear-SM Expert (Rigaku, 2012); program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. The structure of the title compound displacement ellipsoids drawn at the 50% probability level. Symmetry code: (i) 1 - x, 1 - y, -z.
N,N'-Bis(diphenylmethyl)benzene-1,4-diamine top
Crystal data top
C32H28N2F(000) = 468
Mr = 440.56Dx = 1.250 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
a = 14.784 (2) ÅCell parameters from 5636 reflections
b = 5.5853 (8) Åθ = 3.4–27.5°
c = 14.896 (2) ŵ = 0.07 mm1
β = 107.914 (8)°T = 100 K
V = 1170.4 (3) Å3Plate, colourless
Z = 20.1 × 0.09 × 0.02 mm
Data collection top
Rigaku AFC12 (Right)
diffractometer
2664 independent reflections
Radiation source: Rotating Anode1254 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.125
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 3.4°
profile data from ω–scansh = 1918
Absorption correction: multi-scan
(CrystalClear-SM Expert; Rigaku, 2012)
k = 76
Tmin = 0.345, Tmax = 1.000l = 1619
10305 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.077H-atom parameters constrained
wR(F2) = 0.208 w = 1/[σ2(Fo2) + (0.0886P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
2664 reflectionsΔρmax = 0.33 e Å3
155 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: dualExtinction coefficient: 0.026 (5)
Crystal data top
C32H28N2V = 1170.4 (3) Å3
Mr = 440.56Z = 2
Monoclinic, P21/nMo Kα radiation
a = 14.784 (2) ŵ = 0.07 mm1
b = 5.5853 (8) ÅT = 100 K
c = 14.896 (2) Å0.1 × 0.09 × 0.02 mm
β = 107.914 (8)°
Data collection top
Rigaku AFC12 (Right)
diffractometer
2664 independent reflections
Absorption correction: multi-scan
(CrystalClear-SM Expert; Rigaku, 2012)
1254 reflections with I > 2σ(I)
Tmin = 0.345, Tmax = 1.000Rint = 0.125
10305 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0770 restraints
wR(F2) = 0.208H-atom parameters constrained
S = 0.97Δρmax = 0.33 e Å3
2664 reflectionsΔρmin = 0.29 e Å3
155 parameters
Special details top

Experimental. FT—IR data were recorded on a Nicolet ATR FT—IR, while NMR data were collected on a Bruker 400 MHz s pectrometer in CD2Cl2– d2 solutions. The assignment of the chemical shifts for the NMR data were made following numbering shown in structure B. Schiff-base {N1,N4-bis(diphenylmethylene)benzene-1,4-diamine}

IR (ATR cm-1) 1620 (C=N), 1597 and 1570 (phenyl). NMR data (p.p.m.), δH (400 MHz, CD2Cl2): 6.47 (4H, m; C3, 3`, 11, 11`-H), 7.06 (2H, d, J = 7.33 Hz; C15, 15`-H), 7.73 (2H, d, J = 7.33 Hz; C16, 16`-H), 7.27–7.40 (20H, m; aromatic-H); δC (100.63 MHz, CD2Cl2): 121.53–136.75, (aromatic carbon); 140.12 (C6, 6`,8, 8`); 147.37 (C14, 14`); 168.24 (C7, 7`); DEPT 13 C NMR exhibited no signals between 140–170 p.p.m.. The positive ES mass spectrum of the bis-amine showed the parent ion peak at m/z = 441.2362 (M+H)+ (95%) corresponding to C32H28N2; required value = 440.2252. Peaks detected at m/z =247.16 (100%) and 167.09 (98%), correspond to [M-(ph)2CH2)]+ and [M-(ph)2CH2+H2N2ph)]+, respectively.

bis-amine {N1,N4-dibenzhydrylbenzene-1,4-diamine IR (ATR cm-1): 3392 (N—H), 2932; 2873 (C—H) aliphatic, 1599 and 1510 (phenyl). NMR data (p.p.m.), δH (400 MHz, CD2Cl2): 3.95 (2H, S, Na, a`-H), 5.36 (2H, S; C7, 7`-H), 6.37 (4H, d, J=7.33 Hz; C15, 15`, 16, 16`-H), 7.21–7.36 (20H, m, Ar—H); δC (100.63 MHz, CD2Cl2): 49.10 (C7, 7`); 115.21 (C15, 15`, 16, 16`); 127.25–129.04 (aromatic carbon); 140 (C6, 6`, 8, 8`); 144.07 (C14, 14`), DEPT 13 C NMR exhibited no signals between 140–145 p.p.m.. The positive ES mass spectrum of the bis-amine showed the parent ion peak at m/z = 441.2362 (M+H)+ (95%) corresponding to C32H28N2; required value = 440.2252. Peaks detected at m/z =247.16 (100%) and 167.09 (98%), correspond to [M-(ph)2CH2)]+ and [M-(ph)2CH2+H2N2ph)]+, respectively.

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) top
xyzUiso*/Ueq
N10.44891 (16)0.4954 (4)0.1672 (2)0.0366 (7)
H10.41440.61100.17650.044*
C20.47809 (19)0.3103 (5)0.2375 (2)0.0294 (8)
H20.46350.15590.20500.035*
C30.58440 (19)0.3135 (5)0.2909 (2)0.0273 (7)
C40.6426 (2)0.5024 (5)0.2829 (2)0.0295 (8)
H40.61690.63160.24400.035*
C50.7386 (2)0.4993 (5)0.3323 (2)0.0314 (8)
H50.77680.62700.32650.038*
C60.7785 (2)0.3094 (5)0.3901 (2)0.0326 (8)
H60.84310.30800.42310.039*
C70.7208 (2)0.1209 (5)0.3983 (2)0.0329 (8)
H70.74680.00810.43710.039*
C80.6248 (2)0.1228 (5)0.3492 (2)0.0325 (8)
H80.58680.00510.35540.039*
C90.41899 (19)0.3290 (5)0.3050 (2)0.0303 (8)
C100.4294 (2)0.5250 (5)0.3644 (3)0.0392 (9)
H100.47230.64510.36260.047*
C110.3771 (2)0.5438 (6)0.4259 (3)0.0433 (9)
H110.38450.67670.46510.052*
C120.3137 (2)0.3662 (6)0.4296 (3)0.0416 (9)
H120.27820.37850.47120.050*
C130.3032 (2)0.1706 (6)0.3712 (3)0.0421 (10)
H130.26140.04870.37420.051*
C140.3545 (2)0.1546 (5)0.3081 (3)0.0386 (9)
H140.34540.02450.26730.046*
C150.47494 (18)0.4941 (5)0.0834 (2)0.0283 (8)
C160.5290 (2)0.3109 (5)0.0627 (2)0.0315 (8)
H160.54890.18340.10420.038*
C170.44676 (19)0.6813 (5)0.0199 (2)0.0294 (8)
H170.41070.80490.03320.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0298 (14)0.0449 (16)0.039 (2)0.0124 (13)0.0167 (14)0.0079 (14)
C20.0222 (15)0.0330 (16)0.032 (2)0.0024 (13)0.0070 (14)0.0015 (14)
C30.0212 (14)0.0322 (16)0.030 (2)0.0007 (13)0.0109 (14)0.0032 (14)
C40.0244 (15)0.0290 (15)0.035 (2)0.0028 (13)0.0094 (14)0.0020 (14)
C50.0255 (15)0.0340 (17)0.035 (2)0.0023 (14)0.0094 (15)0.0016 (15)
C60.0218 (15)0.0415 (18)0.034 (2)0.0026 (14)0.0076 (15)0.0063 (15)
C70.0279 (16)0.0329 (17)0.039 (2)0.0084 (14)0.0125 (16)0.0026 (15)
C80.0257 (16)0.0318 (17)0.042 (2)0.0006 (13)0.0137 (16)0.0046 (15)
C90.0210 (14)0.0349 (17)0.035 (2)0.0010 (14)0.0089 (14)0.0025 (15)
C100.0319 (17)0.0354 (18)0.053 (3)0.0069 (15)0.0177 (18)0.0066 (17)
C110.0378 (19)0.047 (2)0.048 (3)0.0018 (17)0.0177 (18)0.0068 (18)
C120.0345 (18)0.050 (2)0.048 (3)0.0093 (17)0.0248 (18)0.0082 (18)
C130.0324 (18)0.049 (2)0.053 (3)0.0051 (16)0.0253 (18)0.0042 (18)
C140.0308 (17)0.0357 (17)0.053 (3)0.0058 (15)0.0187 (17)0.0035 (16)
C150.0156 (13)0.0345 (16)0.032 (2)0.0022 (13)0.0039 (14)0.0001 (15)
C160.0219 (14)0.0351 (17)0.037 (2)0.0020 (13)0.0086 (14)0.0049 (15)
C170.0182 (14)0.0350 (17)0.036 (2)0.0025 (13)0.0106 (14)0.0022 (15)
Geometric parameters (Å, º) top
N1—H10.8600C9—C101.386 (4)
N1—C21.440 (4)C9—C141.373 (4)
N1—C151.415 (4)C10—H100.9300
C2—H20.9800C10—C111.372 (4)
C2—C31.528 (4)C11—H110.9300
C2—C91.525 (4)C11—C121.378 (4)
C3—C41.389 (4)C12—H120.9300
C3—C81.388 (4)C12—C131.375 (5)
C4—H40.9300C13—H130.9300
C4—C51.384 (4)C13—C141.380 (4)
C5—H50.9300C14—H140.9300
C5—C61.379 (4)C15—C161.391 (4)
C6—H60.9300C15—C171.385 (4)
C6—C71.384 (4)C16—H160.9300
C7—H70.9300C16—C17i1.384 (4)
C7—C81.382 (4)C17—C16i1.384 (4)
C8—H80.9300C17—H170.9300
C2—N1—H1118.8C10—C9—C2120.1 (2)
C15—N1—H1118.8C14—C9—C2121.2 (3)
C15—N1—C2122.4 (2)C14—C9—C10118.7 (3)
N1—C2—H2107.6C9—C10—H10119.6
N1—C2—C3113.6 (2)C11—C10—C9120.8 (3)
N1—C2—C9109.0 (2)C11—C10—H10119.6
C3—C2—H2107.6C10—C11—H11120.0
C9—C2—H2107.6C10—C11—C12120.1 (3)
C9—C2—C3111.2 (3)C12—C11—H11120.0
C4—C3—C2121.9 (3)C11—C12—H12120.3
C8—C3—C2119.5 (2)C13—C12—C11119.5 (3)
C8—C3—C4118.6 (3)C13—C12—H12120.3
C3—C4—H4119.8C12—C13—H13119.9
C5—C4—C3120.4 (3)C12—C13—C14120.3 (3)
C5—C4—H4119.8C14—C13—H13119.9
C4—C5—H5119.6C9—C14—C13120.6 (3)
C6—C5—C4120.9 (3)C9—C14—H14119.7
C6—C5—H5119.6C13—C14—H14119.7
C5—C6—H6120.6C16—C15—N1122.1 (3)
C5—C6—C7118.9 (3)C17—C15—N1119.5 (3)
C7—C6—H6120.6C17—C15—C16118.5 (3)
C6—C7—H7119.7C15—C16—H16120.1
C8—C7—C6120.6 (3)C17i—C16—C15119.9 (3)
C8—C7—H7119.7C17i—C16—H16120.1
C3—C8—H8119.7C15—C17—H17119.2
C7—C8—C3120.7 (3)C16i—C17—C15121.7 (3)
C7—C8—H8119.7C16i—C17—H17119.2
N1—C2—C3—C410.4 (4)C4—C5—C6—C70.2 (5)
N1—C2—C3—C8169.4 (3)C5—C6—C7—C80.1 (4)
N1—C2—C9—C1067.2 (4)C6—C7—C8—C30.0 (5)
N1—C2—C9—C14112.5 (3)C8—C3—C4—C50.1 (4)
N1—C15—C16—C17i179.5 (3)C9—C2—C3—C4113.0 (3)
N1—C15—C17—C16i179.5 (3)C9—C2—C3—C867.2 (3)
C2—N1—C15—C161.3 (4)C9—C10—C11—C120.4 (5)
C2—N1—C15—C17178.1 (3)C10—C9—C14—C131.9 (5)
C2—C3—C4—C5180.0 (3)C10—C11—C12—C130.0 (5)
C2—C3—C8—C7179.9 (3)C11—C12—C13—C141.3 (5)
C2—C9—C10—C11179.7 (3)C12—C13—C14—C92.3 (5)
C2—C9—C14—C13178.4 (3)C14—C9—C10—C110.6 (5)
C3—C2—C9—C1058.8 (4)C15—N1—C2—C369.6 (3)
C3—C2—C9—C14121.5 (3)C15—N1—C2—C9165.8 (2)
C3—C4—C5—C60.2 (5)C16—C15—C17—C16i0.1 (5)
C4—C3—C8—C70.1 (4)C17—C15—C16—C17i0.1 (4)
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC32H28N2
Mr440.56
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)14.784 (2), 5.5853 (8), 14.896 (2)
β (°) 107.914 (8)
V3)1170.4 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.1 × 0.09 × 0.02
Data collection
DiffractometerRigaku AFC12 (Right)
diffractometer
Absorption correctionMulti-scan
(CrystalClear-SM Expert; Rigaku, 2012)
Tmin, Tmax0.345, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
10305, 2664, 1254
Rint0.125
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.077, 0.208, 0.97
No. of reflections2664
No. of parameters155
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.29

Computer programs: CrystalClear-SM Expert (Rigaku, 2012), SHELXD (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

 

Acknowledgements

The authors would like to thank the `Iraqi Ministry for Higher Education' for providing six months funding for Mr Aeed S. Al-Fahdawi's PhD scholarship.

References

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