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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 3| March 2013| Pages o412-o413

Powder X-ray investigation of 4,4′-diiso­cyano-3,3′-di­methyl­biphen­yl

aDepartment of Chemistry, Atomic Energy Commission of Syria (AECS), PO Box 6091, Damascus, Syrian Arab Republic
*Correspondence e-mail: cscientific@aec.org.sy

(Received 30 January 2013; accepted 13 February 2013; online 20 February 2013)

The title compound, C16H12N2, was investigated in a powder diffraction study and its structure refined utilizing the Rietveld Method. The mol­ecule has approximate C2 symmetry. The dihedral angle between the rings is 25.6 (7)°. The crystal packing is consolidated by weak C—H⋯C N hydrogen-bond-like contacts, which lead to the formation of a three-dimensional network. Further stabilization of the crystal structure is achived by weak non-covalent ππ inter­actions between aromatic rings, with a centroid–centroid distance of 3.839 (8) Å.

Related literature

For disocyano ligands and their coordination complexes, see: Harvey (2001[Harvey, P. D. (2001). Coord. Chem. Rev. 219, 17-52.]); Sakata et al. (2003[Sakata, K., Urabe, K., Hashimoto, M., Yanagi, T., Tsuge, A. & Angelici, R. J. (2003). Synth. React. Inorg. Met. Org. Chem. 33, 11-22.]); Espinet et al. (2000[Espinet, P., Soulantica, K., Charmant, J. P. H. & Orpen, A. G. (2000). Chem. Commun. pp. 915-916.]); Moigno et al. (2002[Moigno, D., Callegas-Gaspar, B., Gil-Rubio, J., Brandt, C. D., Werner, H. & Kiefer, W. (2002). Inorg. Chim. Acta, 334, 355-364.]). For the preparation of the bidentate ligand CNCH2C(CH3)2CH2NC and its organometallic polymeric structures, see: Al-Ktaifani et al. (2008[Al-Ktaifani, M., Rukiah, M. & Shaaban, A. (2008). Pol. J. Chem. 82, 547-557.]); Rukiah & Al-Ktaifani (2008[Rukiah, M. & Al-Ktaifani, M. (2008). Acta Cryst. C64, m170-m172.], 2009[Rukiah, M. & Al-Ktaifani, M. (2009). Acta Cryst. C65, m135-m138.]); Al-Ktaifani & Rukiah (2010[Al-Ktaifani, M. & Rukiah, M. (2010). Acta Cryst. E66, m1555-m1556.]). For chelate complexing, see: Chemin et al. (1996[Chemin, N., D`hardemare, A., Bouquillon, S., Fagret, D. & Vidal, M. (1996). Appl. Radiat. Isot. 47, 479-487.]). For the structure of isocyanide, see: Lentz & Preugschat (1993[Lentz, D. & Preugschat, D. (1993). Acta Cryst. C49, 52-54.]). For practical applications of oganometallic complexes with diisocyanide ligands, see: Fortin et al. (2000[Fortin, D., Drouin, M. & Harvey, P. D. (2000). Inorg. Chem. 39, 2758-2769.]). For standard bond-lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O. & Watson, D. G. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background and details of methods applied in powder diffraction, see: Boultif & Louër (2004[Boultif, A. & Louër, D. (2004). J. Appl. Cryst. 37, 724-731.]); Rodriguez-Carvajal (2001[Rodriguez-Carvajal, J. (2001). FULLPROF. CEA/Saclay, France.]); Roisnel & Rodriguez-Carvajal (2001[Roisnel, T. & Rodriguez-Carvajal, J. (2001). Mater. Sci. Forum, 378-381, 118-123.]); Le Bail et al. (1988[Le Bail, A., Duroy, H. & Fourquet, J. L. (1988). Mater. Res. Bull. 23, 447-452.]); Toby (2001[Toby, B. H. (2001). J. Appl. Cryst. 34, 210-213.]); Thompson et al. (1987[Thompson, P., Cox, D. E. & Hastings, J. B. (1987). J. Appl. Cryst. 20, 79-83.]); Finger et al. (1994[Finger, L. W., Cox, D. E. & Jephcoat, A. P. (1994). J. Appl. Cryst. 27, 892-900.]); Stephens (1999[Stephens, P. W. (1999). J. Appl. Cryst. 32, 281-289.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12N2

  • Mr = 232.28

  • Monoclinic, P 21 /c

  • a = 11.9045 (4) Å

  • b = 14.6235 (4) Å

  • c = 7.61672 (15) Å

  • β = 105.483 (2)°

  • V = 1277.84 (7) Å3

  • Z = 4

  • Cu Kα1 radiation

  • λ = 1.5406 Å

  • μ = 0.56 mm−1

  • T = 298 K

  • flat sheet, 8 × 8 mm

Data collection
  • STOE Transmission STADI P diffractometer

  • Specimen mounting: powder loaded between two Mylar foils

  • Data collection mode: transmission

  • Scan method: step

  • Absorption correction: for a cylinder mounted on the φ axis (GSAS; Larson & Von Dreele, 2004[Larson, A. C. & Von Dreele, R. B. (2004). GSAS. Report LAUR 86-748. LosAlamos National Laboratory, New Mexico, USA.])Tmin = 0.685, Tmax = 0.767

  • 2θmin = 4.999°, 2θmax = 89.979°, 2θstep = 0.02°

Refinement
  • Rp = 0.016

  • Rwp = 0.021

  • Rexp = 0.016

  • R(F2) = 0.026

  • χ2 = 1.742

  • 4250 data points

  • 120 parameters

  • H-atom parameters not refined

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯C14i 0.991 2.900 3.69 (2) 137.36
C7—H7⋯C14ii 0.986 2.815 3.737 (17) 155.86
C16—H16b⋯C1iii 0.989 2.809 3.73 (2) 154.52
Symmetry codes: (i) -x, -y, -z; (ii) x+1, y, z+1; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: WinXPOW (Stoe & Cie, 1999[Stoe & Cie (1999). WinXPOW. Stoe & Cie, Darmstadt, Germany.]); cell refinement: GSAS (Larson & Von Dreele, 2004[Larson, A. C. & Von Dreele, R. B. (2004). GSAS. Report LAUR 86-748. LosAlamos National Laboratory, New Mexico, USA.]); data reduction: WinXPOW; program(s) used to solve structure: FOX (Favre-Nicolin & Černý, 2002[Favre-Nicolin, V. & Černý, R. (2002). J. Appl. Cryst. 35, 734-743.]); program(s) used to refine structure: GSAS; molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Over the past decade a new rich area of organometallic chemistry has been developed in which diisocyanides have been used as potential bridging ligands in the synthesis of bi- and tri- and tetra nuclear complexes and organometallic polymers (Harvey, 2001; Sakata et al., 2003; Espinet et al., 2000; Moigno et al., 2002). These new materials have been reported to have practical potential applications in different fields, such as semi- and photoconductivity and photovoltaic cells (Fortin et al., 2000). Very recently, in a series of publications we have utilized the bidentate ligand 2,2-dimethylpropane-1,3-diyl diisocyanide in the syntheses of the organometallic polymers [Ag(C7H10N2)(X)]n (X = Cl-, Br-, I- or NO3-) (Al-Ktaifani et al., 2008; Al-Ktaifani & Rukiah, 2010; Rukiah & Al-Ktaifani, 2008; Rukiah &Al-Ktaifani, 2009), which have been completely characterized by X-ray powder diffraction studies, IR spectroscopy and micro-analysis. A major point of interest in the previously reported polymers {Ag(I)[CNCH2C(CH3)2CH2NC]X}n (X = Cl-, I- , Br- or NO3-) is their similar polymeric structures regardless of the counterpart anions. Also noteworthy is the bidentate ligand exhibits a very strong tendency to form polymeric complexes rather than dimeric or trimeric complexes suggesting the 2,2-dimethylpropane-1,3-diyl diisocyanide to be a potential bidentate bridging ligand in the syntheses of organometallic polymers of different transition metals. In similar manner, the bidentate bridging ligand 4,4`-diisocyano-3,3`-dimethyl-biphenyl was prepared in order to be utilized in the synthesis of new organometallic complexes. The syntheses of new organometallic complexes of this bidentate bridging ligand and their solid state characterizations are currently under investigations.

In this article, the solid state characterization of the bidentate bridging ligand 4,4`-diisocyano-3,3`-dimethyl-biphenyl (I) is presented. In contrast to the extensively structurally characterized diisocyanide complexes, reports of the molecular structures of free diisocyanides are rare. This was an incentive to described the molecular structure of the uncomplexed diisocyanide 4,4'-diisocyano-3,3'-dimethylbiphenyl, C16H12N2, by powder X-ray diffraction study.

Compound (I) has a tendency to crystalize in the form of very fine beige powder. Since no single-crystal of sufficient thickness and quality could be obtained, a structure determination by powder X-ray diffraction data was attempted. A view of the molecular structure is shown in Fig. 1. Compound (I) crystallizes with one molecule in the asymmetric unit, having a approximate C2 symmetry. In the crystal structure of (I), weak non classical intermolecular hydrogen-bond-like contacts C—H···C (Table 1) between the carbon centre of CH3 or aromatic ring and the carbon center of cyanide group were observed . These contacts link the molecules to form a three-dimensional network and may be effective in the stabilization of the crystal structure (Fig. 2). The crystal packing of (I) is also further stabilized by noncovalent weak ππ aromatic interactions between phenyl rings of adjacent molecule [minimum centroid—centroid distances between two adjacent (but crystallographically different) Cg1···Cg1(x, 1/2 - y, -1/2 - z) = 3.839 (8) Å and Cg1···Cg1(x, 1/2 - y, 1/2 + z) = 3.838 (8) Å, where Cg1 is the centroid of the phenyl C2—C7 ring]. It is notworthy that a contact between two adjecent methyl groups is most likely repulsive and possibly even destabilizing C16···C16(-x, -y, -z-1) = 3.68 (2)Å. All bond distances (Allen et al., 1987) and angles in compound (I) are in their normal ranges.

Related literature top

For disocyano ligands and their coordination complexes, see: Harvey (2001); Sakata et al. (2003); Espinet et al. (2000); Moigno et al. (2002). For the preparation of the bidentate ligand CNCH2C(CH3)2CH2NC and its organometallic polymeric structures, see: Al-Ktaifani et al. (2008); Rukiah & Al-Ktaifani (2008, 2009); Al-Ktaifani & Rukiah (2010). For chelate complexing, see: Chemin et al. (1996). For the structure of isocyanide, see: Lentz & Preugschat (1993). For practical applications of oganometallic complexes with diisocyanide ligands, see: Fortin et al. (2000). For standard bond-lengths, see: Allen et al. (1987). For background and details of methods applied in powder diffraction, see: Boultif & Louër (2004); Rodriguez-Carvajal (2001); Roisnel & Rodriguez-Carvajal (2001); Le Bail et al. (1988); Toby (2001); Thompson et al. (1987); Finger et al. (1994); Stephens (1999).

Experimental top

All reactions and manipulations were carried out in air with reagent grade solvent. 4,4'-diamino-3,3'-dimethylbiphenyl (o-tolidine) was a commercial sample and was used as received. IR spectra were operated on FTIR Thermo Nicolet 6700. Powder X-ray diffraction was performed by Stoe Transmission diffractometre (Stadi P). A round bottom flask was charged with o-tolidine (10 g, 47 mmol), KOH (50%, 50 ml), CH2Cl2 (75 ml) and benzyltriethylammonium chloride (5.3 mmol, 1.2 g). To the mixture was added dropwise CHCl3 (10 ml). The resultant mixture was left to reflux spontaneously and stirred over night. The solution was filtered and diluted with 200 ml of H2O and the product extracted with CH2Cl2. The organic layer was separated, washed with 100 ml of H2O. The organic layer was dried over anhydrous Na2SO4, solvent removed, washed with Et2O to give beige powder. The product was purified by re-crystallization from CH2Cl2 to give light brown powder (3 g, yield 25%, m.p. 389 K). Spectroscopic analysis: IR (KBr, ν, cm-1): 2124.4 (NC); 1H NMR (400 MHz, CDCl3, 298 K) δ 7.39–7.47 (m, aromatic, 6H), 2.52 (s, CH3, 6H).13C{1H} NMR (100 MHz, CDCl3, 298 K) δ 166.91 (s, N C), 140.55 (s, aromatic), 135.59 (s, aromatic), 129.19 (s, aromatic), 127.05 (s, aromatic), 126.15 (s, aromatic), 125.43 (s, aromatic), 18.78 (s, CH3).

Refinement top

No geometric soft restraints were applied during the Rietveld refinement. The methyl and aromatic H atoms were positioned in their idealized geometries. The coordinates of these H atoms were not refined. We used constant isotropic displacement parameters (0.05 Å2) for the aromatic H atoms and (0.1 Å2) for methyl H atoms.The final refinement cycles were performed using anisotropic atomic displacement parameters for the carbon of cyano group. The final Rietveld plot of the X-ray diffraction pattern is given in Fig. 3.

Computing details top

Data collection: WinXPOW (Stoe & Cie, 1999); cell refinement: GSAS (Larson & Von Dreele, 2004); data reduction: WinXPOW (Stoe & Cie, 1999); program(s) used to solve structure: FOX (Favre-Nicolin & Černý, 2002); program(s) used to refine structure: GSAS (Larson & Von Dreele, 2004); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. View of the crystal packing of compound (I).
[Figure 3] Fig. 3. Final Rietveld plot of compound (I). Observed data points are indicated by dots, the best-fit profile (upper trace) and the difference pattern (lower trace) are solid lines. The vertical bars indicate the positions of Bragg peaks.
4,4'-Diisocyano-3,3'-dimethylbiphenyl top
Crystal data top
C16H12N2F(000) = 488
Mr = 232.28Dx = 1.207 Mg m3
Monoclinic, P21/cCu Kα1 radiation, λ = 1.5406 Å
Hall symbol: -P 2ybcµ = 0.56 mm1
a = 11.9045 (4) ÅT = 298 K
b = 14.6235 (4) ÅParticle morphology: Fine powder
c = 7.61672 (15) Ålight_brown
β = 105.483 (2)°flat sheet, 8 × 8 mm
V = 1277.84 (7) Å3Specimen preparation: Prepared at 298 K and 101.3 kPa
Z = 4
Data collection top
STOE Transmission STADI P
diffractometer
Scan method: step
Radiation source: sealed X-ray tubeAbsorption correction: for a cylinder mounted on the ϕ axis
GSAS Absorption/surface roughness correction: function number 4 Flat plate transmission absorption correction Terms = 0.17220 0.0000 Correction is not refined.
Curved Ge(111) monochromatorTmin = 0.685, Tmax = 0.767
Specimen mounting: powder loaded between two Mylar foils2θmin = 4.999°, 2θmax = 89.979°, 2θstep = 0.02°
Data collection mode: transmission
Refinement top
Least-squares matrix: fullExcluded region(s): none
Rp = 0.016Profile function: CW Profile function number 4 with 21 terms Pseudovoigt profile coefficients as parameterized in (Thompson et al.,1987.Asymmetry correction of Finger et al.(Finger et al.,1994). Microstrain broadening by Stephens(Stephens, 1999). #1(GU) = 0.000 #2(GV) = 0.000 #3(GW) = 10.785 #4(GP) = 0.000 #5(LX) = 2.472 #6(ptec) = 0.00 #7(trns) = 0.00 #8(shft) = 0.0000 #9(sfec) = 0.00 #10(S/L) = 0.0225 #11(H/L) = 0.0225 #12(eta) = 0.4987 #13(S400 ) = 9.0E-02 #14(S040 ) = 1.1E-02 #15(S004 ) = 2.8E+00 #16(S220 ) = 1.9E-02 #17(S202 ) = -1.5E-02 #18(S022 ) = 3.5E-02 #19(S301 ) = -2.0E-01 #20(S103 ) = 1.1E+00 #21(S121 ) = -6.1E-02 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0
Rwp = 0.021120 parameters
Rexp = 0.0160 restraints
R(F2) = 0.02609H-atom parameters not refined
χ2 = 1.742(Δ/σ)max = 0.02
4250 data pointsBackground function: GSAS Background function number 1 with 20 terms. Shifted Chebyshev function of 1st kind 1: 3509.16 2: -3547.18 3: 1729.31 4: -271.390 5: -158.493 6: 133.640 7: -41.5743 8: -87.6309 9: 73.0201 10: 78.1201 11: -126.319 12: 73.5124 13: 5.65073 14: -38.9623 15: 13.5948 16: 6.87496 17: -4.39687 18: 0.392461 19: 8.77696 20: -6.87661
Crystal data top
C16H12N2V = 1277.84 (7) Å3
Mr = 232.28Z = 4
Monoclinic, P21/cCu Kα1 radiation, λ = 1.5406 Å
a = 11.9045 (4) ŵ = 0.56 mm1
b = 14.6235 (4) ÅT = 298 K
c = 7.61672 (15) Åflat sheet, 8 × 8 mm
β = 105.483 (2)°
Data collection top
STOE Transmission STADI P
diffractometer
Absorption correction: for a cylinder mounted on the ϕ axis
GSAS Absorption/surface roughness correction: function number 4 Flat plate transmission absorption correction Terms = 0.17220 0.0000 Correction is not refined.
Specimen mounting: powder loaded between two Mylar foilsTmin = 0.685, Tmax = 0.767
Data collection mode: transmission2θmin = 4.999°, 2θmax = 89.979°, 2θstep = 0.02°
Scan method: step
Refinement top
Rp = 0.0164250 data points
Rwp = 0.021120 parameters
Rexp = 0.0160 restraints
R(F2) = 0.02609H-atom parameters not refined
χ2 = 1.742
Special details top

Experimental. The sample was ground lightly in a mortar, loaded between two Mylar foils and fixed in the sample holder with a mask of 8.0 mm internal diameter.

Refinement. For pattern indexing, the extraction of the peak positions was carried out with the programWinPLOTR (Roisnel & Rodriguez-Carvajal, 2001). Pattern indexing was performed with the program DicVol4.0 (Boultif & Louër, 2004). The first 20 lines of powder pattern were completely indexed on the basis of monoclinic system. The absolute error on each observed line was fixed at 0.02° (2θ). The figures of merit are sufficiently high to support the obtained indexing results [M(20) = 22.5, F(20) = 41.1(0.0087, 56)]. The whole powder diffraction pattern from 5 to 90° (2θ) was subsequently refined with cell and resolution constraints (Le Bail et al., 1988) with a space group without systematic extinctions in monoclinic system, P2/m, using the "profile matching" option of the program FullProf (Rodriguez-Carvajal, 2001). The best estimated space group in the monoclinic system was P21/c which determined with the help of the program Check Group interfaced by WinPLOTR (Roisnel & Rodriguez, 2001). The number of molecules per unit cell was estimated to be equal to Z = 4, it can be concluded that the number of molecules in the asymmetric unit is Z' = 1 for the space group P21/c.

The structure was solved ab initio by direct space method (Monte Carlo simulated annealing with parallel tempering algorithm) using the program FOX (Favre-Nicolin & Černý, 2002). The model found by this program was introduced in the program GSAS (Larson & Von Dreele, 2004) implemented in EXPGUI (Toby, 2001) for Rietveld refinements. The background was refined using a shifted Chebyshev polynomial with 20 coefficients. During the Rietveld refinements, the effect of the asymmetry of peaks was corrected using a pseudo-Voigt description of the peak shape (Thompson et al., 1987) which allows for angle-dependent asymmetry with axial divergence (Finger et al., 1994). The two asymmetry parameters of this function S/L and D/L were both fixed at 0.0225 during the Rietveld refinement. Intensities were corrected from absorption effects with a µ.d value of 0.1722.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7040 (15)0.3220 (13)0.546 (3)0.13957
C20.5080 (12)0.2651 (12)0.326 (2)0.049 (7)*
C30.4211 (14)0.3265 (8)0.237 (2)0.031 (5)*
C40.3141 (13)0.2954 (10)0.1285 (17)0.033 (5)*
C50.2881 (12)0.2038 (10)0.120 (2)0.027 (5)*
C60.3738 (13)0.1398 (8)0.209 (2)0.035 (6)*
C70.4835 (12)0.1710 (10)0.3129 (17)0.044 (6)*
C80.1712 (13)0.1714 (10)0.0015 (19)0.022 (5)*
C90.1588 (12)0.0804 (10)0.075 (2)0.034 (5)*
C100.0455 (16)0.0559 (9)0.181 (2)0.039 (6)*
C110.0471 (12)0.1147 (11)0.213 (2)0.049 (6)*
C120.0348 (12)0.2013 (10)0.1276 (19)0.039 (6)*
C130.0750 (14)0.2270 (7)0.030 (2)0.043 (6)*
C140.2511 (14)0.0608 (10)0.386 (2)0.11783
C150.4492 (9)0.4276 (9)0.2552 (18)0.086 (6)*
C160.0322 (13)0.0402 (9)0.2630 (19)0.060 (5)*
N10.6187 (12)0.2921 (10)0.449 (2)0.065 (7)*
N20.1575 (11)0.0800 (9)0.3173 (19)0.046 (6)*
H40.257190.34310.066710.05*
H60.353130.074030.195770.05*
H70.539980.124580.376350.05*
H90.22640.042730.059120.05*
H120.103720.238950.15330.05*
H130.080750.290470.025420.05*
H15a0.4380.452360.133970.1*
H15b0.394510.455590.31310.1*
H15c0.527580.436610.326690.1*
H16a0.048740.041780.381380.1*
H16b0.084450.084710.183260.1*
H16c0.047780.061160.27770.1*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.13 (2)0.21 (2)0.07 (2)0.001 (18)0.004 (15)0.048 (17)
C140.081 (18)0.127 (18)0.11 (2)0.014 (14)0.033 (19)0.063 (15)
Geometric parameters (Å, º) top
C1—N11.171 (19)C5—C81.518 (13)
N1—C21.451 (17)C8—C91.446 (14)
C2—C31.402 (18)C9—C101.421 (18)
C3—C41.397 (17)C9—H90.956
C3—C151.513 (14)C10—C111.367 (16)
C15—H15a0.967C10—C161.528 (19)
C15—H15b0.969C16—H16a0.973
C15—H15c0.956C16—H16b0.989
C4—C51.372 (13)C16—H16c0.978
C4—H40.998C11—C121.414 (14)
C5—C61.416 (14)C11—N21.435 (15)
C6—C71.410 (14)C12—C131.373 (14)
C6—H60.992C12—H120.964
C7—C21.404 (14)C13—H131.014
C7—H70.987C14—N21.133 (15)
C3—C2—C7118.7 (14)C9—C10—C16116.3 (18)
C3—C2—N1124.3 (17)C11—C10—C16121.0 (18)
C7—C2—N1116.7 (19)C10—C11—C12120.1 (15)
C2—C3—C4121.1 (12)C10—C11—N2116.9 (18)
C2—C3—C15117.7 (16)C12—C11—N2122.6 (18)
C4—C3—C15121.2 (16)C11—C12—C13117.5 (14)
C3—C4—C5120.3 (14)C11—C12—H12116.1
C3—C4—H4116.6C13—C12—H12126.1
C5—C4—H4123.0C8—C13—C12124.2 (15)
C4—C5—C6119.9 (15)C8—C13—H13120.6
C4—C5—C8119.5 (16)C12—C13—H13115.1
C6—C5—C8120.5 (13)C3—C15—H15a107.9
C5—C6—C7119.7 (14)C3—C15—H15b107.2
C5—C6—H6117.7C3—C15—H15c110.2
C7—C6—H6122.5H15a—C15—H15b109.7
C2—C7—C6120.1 (13)H15a—C15—H15c110.9
C2—C7—H7122.5H15b—C15—H15c110.8
C6—C7—H7117.4C10—C16—H16a112.1
C5—C8—C9120.4 (13)C10—C16—H16b112.0
C5—C8—C13120.6 (15)C10—C16—H16c109.1
C9—C8—C13119.0 (16)H16a—C16—H16b107.6
C8—C9—C10116.1 (14)H16a—C16—H16c108.6
C8—C9—H9119.2H16b—C16—H16c107.3
C10—C9—H9124.6C1—N1—C2174 (3)
C9—C10—C11122.7 (14)C11—N2—C14171 (2)
N1—C2—C3—C4176.4 (14)C6—C5—C8—C13156.0 (15)
N1—C2—C3—C156 (2)C5—C6—C7—C21 (2)
C7—C2—C3—C44 (2)C5—C8—C9—C10178.8 (13)
C7—C2—C3—C15179.3 (13)C13—C8—C9—C101 (2)
N1—C2—C7—C6174.5 (13)C5—C8—C13—C12176.6 (14)
C3—C2—C7—C61 (2)C9—C8—C13—C122 (2)
C2—C3—C4—C56 (2)C8—C9—C10—C111 (2)
C15—C3—C4—C5177.1 (13)C8—C9—C10—C16179.7 (13)
C3—C4—C5—C65 (2)C9—C10—C11—N2178.0 (14)
C3—C4—C5—C8179.9 (13)C9—C10—C11—C125 (2)
C4—C5—C6—C73 (2)C16—C10—C11—N24 (2)
C8—C5—C6—C7177.6 (13)C16—C10—C11—C12176.4 (13)
C4—C5—C8—C9152.6 (14)N2—C11—C12—C13179.5 (14)
C4—C5—C8—C1329 (2)C10—C11—C12—C137 (2)
C6—C5—C8—C922 (2)C11—C12—C13—C85 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···C14i0.9912.9003.69 (2)137.36
C7—H7···C14ii0.9862.8153.737 (17)155.86
C16—H16b···C1iii0.9892.8093.73 (2)154.52
C16—H16a···C16iv0.9732.8833.68 (2)139.57
Symmetry codes: (i) x, y, z; (ii) x+1, y, z+1; (iii) x+1, y1/2, z+1/2; (iv) x, y, z1.

Experimental details

Crystal data
Chemical formulaC16H12N2
Mr232.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.9045 (4), 14.6235 (4), 7.61672 (15)
β (°) 105.483 (2)
V3)1277.84 (7)
Z4
Radiation typeCu Kα1, λ = 1.5406 Å
µ (mm1)0.56
Specimen shape, size (mm)Flat sheet, 8 × 8
Data collection
DiffractometerSTOE Transmission STADI P
diffractometer
Specimen mountingPowder loaded between two Mylar foils
Data collection modeTransmission
Scan methodStep
Absorption correctionFor a cylinder mounted on the ϕ axis
GSAS Absorption/surface roughness correction: function number 4 Flat plate transmission absorption correction Terms = 0.17220 0.0000 Correction is not refined.
Tmin, Tmax0.685, 0.767
2θ values (°)2θmin = 4.999 2θmax = 89.979 2θstep = 0.02
Refinement
R factors and goodness of fitRp = 0.016, Rwp = 0.021, Rexp = 0.016, R(F2) = 0.02609, χ2 = 1.742
No. of data points4250
No. of parameters120
H-atom treatmentH-atom parameters not refined

Computer programs: WinXPOW (Stoe & Cie, 1999), GSAS (Larson & Von Dreele, 2004), FOX (Favre-Nicolin & Černý, 2002), ORTEP-3 (Farrugia, 2012), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···C14i0.9912.9003.69 (2)137.36
C7—H7···C14ii0.9862.8153.737 (17)155.86
C16—H16b···C1iii0.9892.8093.73 (2)154.52
Symmetry codes: (i) x, y, z; (ii) x+1, y, z+1; (iii) x+1, y1/2, z+1/2.
 

Acknowledgements

The authors thank Professors I. Othman, Director General, and. T. Yassine, Head of Chemistry Department, for their support and encouragement.

References

First citationAl-Ktaifani, M. & Rukiah, M. (2010). Acta Cryst. E66, m1555–m1556.  Web of Science CrossRef IUCr Journals
First citationAl-Ktaifani, M., Rukiah, M. & Shaaban, A. (2008). Pol. J. Chem. 82, 547–557.  CAS
First citationAllen, F. H., Kennard, O. & Watson, D. G. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationBoultif, A. & Louër, D. (2004). J. Appl. Cryst. 37, 724–731.  Web of Science CrossRef CAS IUCr Journals
First citationChemin, N., D`hardemare, A., Bouquillon, S., Fagret, D. & Vidal, M. (1996). Appl. Radiat. Isot. 47, 479–487.
First citationEspinet, P., Soulantica, K., Charmant, J. P. H. & Orpen, A. G. (2000). Chem. Commun. pp. 915–916.  Web of Science CSD CrossRef
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationFavre-Nicolin, V. & Černý, R. (2002). J. Appl. Cryst. 35, 734–743.  Web of Science CrossRef CAS IUCr Journals
First citationFinger, L. W., Cox, D. E. & Jephcoat, A. P. (1994). J. Appl. Cryst. 27, 892–900.  CrossRef CAS Web of Science IUCr Journals
First citationFortin, D., Drouin, M. & Harvey, P. D. (2000). Inorg. Chem. 39, 2758–2769.  Web of Science CSD CrossRef PubMed CAS
First citationHarvey, P. D. (2001). Coord. Chem. Rev. 219, 17–52.  Web of Science CrossRef
First citationLarson, A. C. & Von Dreele, R. B. (2004). GSAS. Report LAUR 86-748. LosAlamos National Laboratory, New Mexico, USA.
First citationLe Bail, A., Duroy, H. & Fourquet, J. L. (1988). Mater. Res. Bull. 23, 447–452.  CrossRef CAS Web of Science
First citationLentz, D. & Preugschat, D. (1993). Acta Cryst. C49, 52–54.  CSD CrossRef CAS Web of Science IUCr Journals
First citationMoigno, D., Callegas-Gaspar, B., Gil-Rubio, J., Brandt, C. D., Werner, H. & Kiefer, W. (2002). Inorg. Chim. Acta, 334, 355–364.  Web of Science CSD CrossRef CAS
First citationRodriguez-Carvajal, J. (2001). FULLPROF. CEA/Saclay, France.
First citationRoisnel, T. & Rodriguez-Carvajal, J. (2001). Mater. Sci. Forum, 378–381, 118–123.  CrossRef CAS
First citationRukiah, M. & Al-Ktaifani, M. (2008). Acta Cryst. C64, m170–m172.  Web of Science CSD CrossRef IUCr Journals
First citationRukiah, M. & Al-Ktaifani, M. (2009). Acta Cryst. C65, m135–m138.  Web of Science CSD CrossRef CAS IUCr Journals
First citationSakata, K., Urabe, K., Hashimoto, M., Yanagi, T., Tsuge, A. & Angelici, R. J. (2003). Synth. React. Inorg. Met. Org. Chem. 33, 11–22.  Web of Science CrossRef CAS
First citationStephens, P. W. (1999). J. Appl. Cryst. 32, 281–289.  Web of Science CrossRef CAS IUCr Journals
First citationStoe & Cie (1999). WinXPOW. Stoe & Cie, Darmstadt, Germany.
First citationThompson, P., Cox, D. E. & Hastings, J. B. (1987). J. Appl. Cryst. 20, 79–83.  CrossRef CAS Web of Science IUCr Journals
First citationToby, B. H. (2001). J. Appl. Cryst. 34, 210–213.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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 69| Part 3| March 2013| Pages o412-o413
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds