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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Pages o1463-o1464

2,4,6-Tris(2,4-di­methyl­phen­yl)-1,3,5-triazine

aSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, People's Republic of China, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 10 April 2012; accepted 14 April 2012; online 21 April 2012)

Two virtually superimposable mol­ecules comprise the asymmetric unit of the title compound, C27H27N3. The range of dihedral angles between the central 1,3,5-triazine ring and the attached benzene rings is 20.88 (14)–31.36 (14)°, and the shape of each mol­ecule is of a flattened bowl. The crystal packing features weak C—H⋯π bonds and ππ inter­actions between triazine and benzene rings [centroid–centroid separations = 3.7696 (17) and 3.7800 (18) Å] that result in the formation of supra­molecular layers in the ac plane. The crystal studied was a non-merohedral twin with a minor twin component of 20.7 (3)%.

Related literature

For the synthesis, see: Orban et al. (1988[Orban, I., Holer, M. & Kaufmann, A. (1988). US Patent No. 5726310.]). For the crystal structure of s-triphenyl­triazine, see: Damiani et al. (1965[Damiani, A., Giglio, E. & Ripamonti, A. (1965). Acta Cryst. 19, 161-168.]). For homologues, see: Bosch & Barnes (2002[Bosch, E. & Barnes, C. L. (2002). Inorg. Chem. 41, 2543-2547.]); Thalladi et al. (1999[Thalladi, V. R., Muthuraman, M., Nangia, A. & Desiraju, G. R. (1999). Acta Cryst. C55, 698-700.]); Volkis et al. (2003[Volkis, V., Nelkenbau, E., Lisovskii, A., Hasson, G., Semiat, R., Kapon, M., Botoshansky, M., Eishen, Y. & Eisen, M. S. (2003). J. Am. Chem. Soc. 125, 2179-2194.]). For the separation of twinned diffraction indices, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C27H27N3

  • Mr = 393.52

  • Triclinic, [P \overline 1]

  • a = 7.4663 (4) Å

  • b = 15.0789 (13) Å

  • c = 19.7266 (12) Å

  • α = 109.016 (7)°

  • β = 90.949 (5)°

  • γ = 93.717 (6)°

  • V = 2093.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.30 × 0.15 × 0.05 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.978, Tmax = 0.996

  • 14777 measured reflections

  • 9605 independent reflections

  • 5518 reflections with I > 2σ(I)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.085

  • wR(F2) = 0.222

  • S = 1.04

  • 9597 reflections

  • 554 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1–Cg4 are the centroids of the C39–C44, C31–C36, C12–C17 and C4–C9 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11BCg1i 0.98 2.97 3.777 (4) 140
C18—H18BCg2ii 0.98 2.91 3.688 (4) 137
C38—H38CCg3iii 0.98 2.84 3.756 (4) 155
C45—H45BCg4iv 0.98 2.77 3.596 (4) 142
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+1, -z+2; (iii) -x+1, -y+1, -z+2; (iv) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]), Qmol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

s-Triphenyltriazine forms a number of adducts with metal salts; its crystal structure was reported some time ago (Damiani et al., 1965). The crystal structures of substituted derivatives have also been reported, e.g. the p-tolyl (Thalladi et al., 1999; Volkis et al., 2003). The structure of tris(mesityl)-1,3,5-triazine is known as its silver adduct (Bosch & Barnes, 2002). Herein, the crystal and molecular structure of 2,4,6-tris(2,4-dimethylphenyl)-1,3,5-triazine (I) is described.

Two independent molecules comprise the crystallographic asymmetric unit of (I), Fig. 1. The molecules are virtually superimposable as seen from the overlay diagram, Fig. 2. With respect to the central 1,3,5-triazine ring with the N1—N3 atoms, the dihedral angles with the attached benzene rings C4—C9, C12—C17 and C20—C25 are 29.75 (15), 26.26 (15) and 21.22 (15)°, respectively. The comparable dihedral angles for the N4—N6 triazine and the C31—C36, C39—C44 and C47—C52 rings are 25.23 (15), 31.36 (14) and 20.88 (14)°, respectively. Within each molecule, one of the 2,4-dimethylphenyl residues is orientated in the opposite direction to the other two so that the molecules do not have molecular 3-fold symmetry. Overall, the shape of each molecule is of a flattened bowl.

The crystal packing is dominated by C—H···π, Table 1, and ππ interactions. The former occur between the independent molecules with each forming two donor and two acceptor interactions. The ππ interactions occur between like molecules with the shortest contacts occurring between triazine and benzene rings [inter-centroid (N1-triazine)···(C20–C25)i distance = 3.7800 (18) Å, angle of inclination = 21.22 (15)° for symmetry operation i: 1 - x, 1 - y, 2 - z, and inter-centroid (N4-triazine)···(C47–C52)ii distance = 3.7696 (17) Å, angle of inclination = 20.88 (14)° for symmetry operation i: -x, 1 - y, 2 - z]. The result is the formation of supramolecular layers in the ac plane that stack along the b axis with no specific interactions between them, Fig. 3.

Related literature top

For the synthesis, see: Orban et al. (1988). For the crystal structure of s-triphenyltriazine, see: Damiani et al. (1965). For homologues, see: Bosch & Barnes (2002); Thalladi et al. (1999); Volkis et al. (2003). For the separation of twinned diffraction indices, see: Spek (2009).

Experimental top

The compound was synthesized by the Friedel-Crafts arylation of cyanuric chloride with excess m-xylene in the presence of aluminium trichloride (Orban et al., 1988).

Aluminium chloride (8.7 g, 0.066 mol) was added to cyanuric chloride (4.0 g, 0.022 mol) in chlorobenzene (20 ml). The suspension was stirred by spinning a stirrer at about 250 rpm. It was then heated at 358 K for 20 min. m-Xylene (3.0 ml, 0.0242 mol) was added over 30 min; the reaction was exothermic. A second 3 ml portion was added over the next 30 min. The small amount of hydrogen chloride gas that was released was neutralized by 5% sodium hydroxide. A further 3 ml was added over 30 min while keeping the mixture heated at 373 K. The dark-brown reaction mixture was additionally stirred at 378 K for another 20 min.

The warm reaction mixture was added to water (30 ml). The mixture was stirred at 333 K for 10 min. The organic phase was separated and treated with 5% hydrochloric acid. This procedure was repeated.

The solvent was removed and the dark-brown residue was dried at 373 K. It was then transferred it into a 100 ml distillation flask. Toluene (50 ml) was added and the mixture heated at 348 K. To this was added ethanol (15 ml). The solution was set aside for the crystallization of the compound to give 5.4 g of a light-yellow product. The pure compound was obtained as colourless plates after recrystallization from a toluene and ethanol (5:1) mixture in a yield of 3.5 g.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C—H = 0.95 to 0.98 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation. The crystal is a non-merohedral twin with a twin component of 20.7 (3)%; the twin components were identified by the TwinRotMat routine in PLATON (Spek, 2009).

Owing to poor agreement several reflections, i.e. (4 2 4), (3 5 16), (4 4 6), (4 1 0), (4 3 8), (3 5 16), (4 4 0) and (4 2 2), were omitted from the final refinement.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001), Qmol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structures of the two independent molecules comprising the asymmetric unit of (I) showing displacement ellipsoids at the 70% probability level.
[Figure 2] Fig. 2. An overlay diagram of two independent molecules in (I). The N1-containing molecule is illustrated in red and the N4-molecule in blue. Molecules have been aligned so that the N1,N2,N3 and N5,N6,N4 planes are overlapped.
[Figure 3] Fig. 3. A view in projection down the c axis of the unit-cell contents for (I). The C—H···π and ππ interactions are shown as purple and orange dashed lines, respectively.
2,4,6-Tris(2,4-dimethylphenyl)-1,3,5-triazine top
Crystal data top
C27H27N3Z = 4
Mr = 393.52F(000) = 840
Triclinic, P1Dx = 1.248 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4663 (4) ÅCell parameters from 2806 reflections
b = 15.0789 (13) Åθ = 2.7–27.5°
c = 19.7266 (12) ŵ = 0.07 mm1
α = 109.016 (7)°T = 100 K
β = 90.949 (5)°Plate, colourless
γ = 93.717 (6)°0.30 × 0.15 × 0.05 mm
V = 2093.6 (2) Å3
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
9605 independent reflections
Radiation source: SuperNova (Mo) X-ray Source5518 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.058
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 2.7°
ω scanh = 97
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 1619
Tmin = 0.978, Tmax = 0.996l = 2525
14777 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)] = 0.085Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0673P)2 + 1.4043P]
where P = (Fo2 + 2Fc2)/3
9597 reflections(Δ/σ)max = 0.001
554 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C27H27N3γ = 93.717 (6)°
Mr = 393.52V = 2093.6 (2) Å3
Triclinic, P1Z = 4
a = 7.4663 (4) ÅMo Kα radiation
b = 15.0789 (13) ŵ = 0.07 mm1
c = 19.7266 (12) ÅT = 100 K
α = 109.016 (7)°0.30 × 0.15 × 0.05 mm
β = 90.949 (5)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
9605 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
5518 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.996Rint = 0.058
14777 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0850 restraints
wR(F2) = 0.222H-atom parameters constrained
S = 1.04Δρmax = 0.36 e Å3
9597 reflectionsΔρmin = 0.39 e Å3
554 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2281 (4)0.3830 (2)0.89667 (14)0.0177 (6)
N20.2497 (4)0.2425 (2)0.92575 (14)0.0178 (6)
N30.2594 (4)0.3902 (2)1.01875 (14)0.0169 (6)
N40.2354 (3)0.6128 (2)0.57186 (14)0.0164 (6)
N50.2624 (4)0.6141 (2)0.45247 (14)0.0171 (6)
N60.2400 (4)0.7575 (2)0.54849 (14)0.0183 (6)
C10.2352 (4)0.2892 (2)0.87866 (17)0.0164 (7)
C20.2602 (4)0.2959 (2)0.99515 (17)0.0169 (7)
C30.2415 (4)0.4304 (2)0.96749 (17)0.0160 (7)
C40.2182 (4)0.2313 (2)0.80171 (18)0.0180 (7)
C50.2769 (4)0.2636 (2)0.74558 (18)0.0197 (7)
C60.2461 (4)0.2028 (3)0.67513 (18)0.0205 (8)
H60.28470.22380.63690.025*
C70.1615 (5)0.1129 (3)0.65849 (18)0.0213 (8)
C80.1094 (4)0.0810 (2)0.71473 (18)0.0199 (7)
H80.05440.01930.70480.024*
C90.1381 (4)0.1396 (2)0.78498 (18)0.0195 (7)
H90.10260.11710.82280.023*
C100.3764 (5)0.3579 (3)0.75557 (18)0.0235 (8)
H10A0.45850.37460.79780.035*
H10B0.28990.40600.76240.035*
H10C0.44510.35430.71300.035*
C110.1230 (5)0.0521 (3)0.58162 (18)0.0277 (9)
H11A0.21090.06960.55100.042*
H11B0.00180.06120.56640.042*
H11C0.13100.01410.57740.042*
C120.2612 (4)0.2466 (2)1.04930 (17)0.0172 (7)
C130.1863 (5)0.1538 (2)1.02738 (18)0.0203 (8)
H130.15090.12340.97830.024*
C140.1624 (5)0.1049 (3)1.07584 (18)0.0219 (8)
H140.11000.04211.05970.026*
C150.2147 (4)0.1475 (2)1.14763 (18)0.0185 (7)
C160.2977 (4)0.2383 (2)1.16825 (18)0.0202 (8)
H160.33870.26681.21690.024*
C170.3236 (4)0.2895 (2)1.12107 (17)0.0181 (7)
C180.1833 (5)0.0972 (3)1.20146 (19)0.0264 (8)
H18A0.12050.03541.17760.040*
H18B0.11010.13441.23970.040*
H18C0.29890.08921.22210.040*
C190.4222 (5)0.3859 (2)1.15022 (18)0.0229 (8)
H19A0.49350.39031.19350.034*
H19B0.33500.43401.16210.034*
H19C0.50180.39581.11390.034*
C200.2397 (4)0.5344 (2)0.99277 (17)0.0159 (7)
C210.3143 (4)0.5832 (2)1.06164 (17)0.0177 (7)
H210.35770.54841.09010.021*
C220.3266 (4)0.6807 (2)1.08958 (18)0.0193 (7)
H220.37760.71181.13650.023*
C230.2634 (4)0.7331 (2)1.04829 (18)0.0185 (7)
C240.1862 (4)0.6847 (2)0.98088 (18)0.0200 (7)
H240.14130.72000.95320.024*
C250.1710 (4)0.5862 (2)0.95141 (17)0.0184 (7)
C260.2836 (5)0.8396 (3)1.0768 (2)0.0288 (9)
H26A0.25110.86451.03850.043*
H26B0.40850.86061.09330.043*
H26C0.20430.86251.11690.043*
C270.0759 (5)0.5441 (3)0.87846 (18)0.0223 (8)
H27A0.00370.59100.86880.033*
H27B0.00250.48910.87770.033*
H27C0.16500.52490.84150.033*
C280.2320 (4)0.7064 (2)0.59323 (17)0.0171 (7)
C290.2525 (4)0.5694 (2)0.50159 (17)0.0156 (7)
C300.2538 (4)0.7078 (2)0.47921 (17)0.0160 (7)
C310.2327 (4)0.7581 (2)0.67135 (17)0.0170 (7)
C320.1785 (4)0.7160 (2)0.72288 (18)0.0188 (7)
C330.2087 (4)0.7689 (3)0.79568 (18)0.0209 (8)
H330.17460.74080.83070.025*
C340.2864 (4)0.8609 (3)0.81899 (18)0.0202 (8)
C350.3299 (5)0.9030 (2)0.76749 (18)0.0212 (8)
H350.37840.96650.78190.025*
C360.3023 (4)0.8519 (2)0.69500 (18)0.0204 (8)
H360.33160.88160.66050.024*
C370.0851 (5)0.6187 (2)0.70535 (18)0.0230 (8)
H37A0.01800.61470.74670.034*
H37B0.17480.57190.69420.034*
H37C0.00210.60640.66380.034*
C380.3233 (5)0.9130 (3)0.89758 (18)0.0273 (9)
H38A0.21760.90480.92430.041*
H38B0.35000.98000.90490.041*
H38C0.42640.88810.91470.041*
C390.2682 (4)0.7613 (2)0.42778 (17)0.0155 (7)
C400.3514 (4)0.8527 (2)0.45439 (18)0.0184 (7)
H400.38590.87840.50390.022*
C410.3844 (4)0.9064 (2)0.40997 (18)0.0193 (7)
H410.44300.96770.42900.023*
C420.3317 (4)0.8704 (2)0.33773 (18)0.0191 (7)
C430.2414 (4)0.7819 (2)0.31238 (18)0.0195 (7)
H430.19980.75840.26360.023*
C440.2091 (4)0.7257 (2)0.35570 (18)0.0175 (7)
C450.3768 (5)0.9246 (2)0.28692 (19)0.0218 (8)
H45A0.27260.91970.25470.033*
H45B0.47890.89820.25860.033*
H45C0.40790.99080.31460.033*
C460.1078 (5)0.6305 (2)0.32061 (18)0.0242 (8)
H46A0.02050.61850.35370.036*
H46B0.19290.58130.30890.036*
H46C0.04470.63020.27660.036*
C470.2593 (4)0.4660 (2)0.47766 (17)0.0167 (7)
C480.3293 (4)0.4124 (3)0.41262 (18)0.0198 (8)
C490.3207 (4)0.3143 (3)0.39598 (18)0.0203 (8)
H490.36740.27780.35190.024*
C500.2477 (4)0.2679 (2)0.44048 (19)0.0200 (7)
C510.1841 (4)0.3229 (2)0.50602 (18)0.0203 (8)
H510.13630.29350.53830.024*
C520.1902 (4)0.4195 (2)0.52416 (17)0.0173 (7)
H520.14690.45550.56900.021*
C530.4187 (5)0.4523 (3)0.35912 (18)0.0219 (8)
H53A0.49510.40610.32870.033*
H53B0.49240.51010.38500.033*
H53C0.32640.46660.32910.033*
C540.2342 (5)0.1619 (2)0.4188 (2)0.0269 (8)
H54A0.24630.14310.46160.040*
H54B0.33030.13690.38630.040*
H54C0.11740.13690.39440.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0190 (15)0.0186 (16)0.0168 (15)0.0022 (11)0.0005 (11)0.0072 (12)
N20.0189 (15)0.0212 (16)0.0149 (15)0.0009 (11)0.0018 (11)0.0088 (13)
N30.0200 (15)0.0170 (15)0.0151 (15)0.0002 (11)0.0005 (11)0.0075 (12)
N40.0181 (15)0.0171 (15)0.0148 (15)0.0004 (11)0.0002 (11)0.0065 (12)
N50.0203 (15)0.0178 (15)0.0159 (15)0.0018 (11)0.0017 (11)0.0091 (12)
N60.0215 (15)0.0194 (16)0.0151 (15)0.0016 (12)0.0004 (11)0.0078 (12)
C10.0154 (17)0.0183 (18)0.0160 (17)0.0022 (13)0.0027 (12)0.0061 (14)
C20.0159 (17)0.0190 (18)0.0158 (17)0.0002 (13)0.0007 (12)0.0059 (14)
C30.0151 (17)0.0221 (19)0.0129 (17)0.0009 (13)0.0002 (12)0.0088 (14)
C40.0179 (17)0.0206 (19)0.0168 (17)0.0042 (13)0.0003 (12)0.0073 (15)
C50.0195 (18)0.0221 (19)0.0200 (18)0.0018 (14)0.0001 (13)0.0101 (15)
C60.0195 (18)0.028 (2)0.0162 (18)0.0071 (14)0.0010 (13)0.0100 (16)
C70.0214 (19)0.027 (2)0.0150 (18)0.0065 (14)0.0000 (13)0.0048 (15)
C80.0174 (18)0.0193 (19)0.0227 (19)0.0026 (13)0.0002 (13)0.0062 (15)
C90.0203 (18)0.0215 (19)0.0196 (18)0.0010 (14)0.0008 (13)0.0108 (15)
C100.028 (2)0.027 (2)0.0194 (19)0.0045 (15)0.0058 (14)0.0115 (16)
C110.025 (2)0.033 (2)0.022 (2)0.0002 (16)0.0011 (14)0.0046 (17)
C120.0183 (17)0.0188 (18)0.0178 (18)0.0052 (13)0.0022 (12)0.0098 (15)
C130.0250 (19)0.0174 (19)0.0178 (18)0.0001 (14)0.0005 (14)0.0050 (15)
C140.027 (2)0.0180 (19)0.024 (2)0.0019 (14)0.0023 (14)0.0117 (16)
C150.0186 (18)0.0202 (19)0.0214 (19)0.0046 (13)0.0037 (13)0.0124 (15)
C160.0230 (19)0.022 (2)0.0161 (18)0.0034 (14)0.0002 (13)0.0071 (15)
C170.0179 (17)0.0230 (19)0.0156 (17)0.0019 (13)0.0019 (12)0.0093 (15)
C180.031 (2)0.029 (2)0.025 (2)0.0021 (16)0.0009 (15)0.0173 (17)
C190.029 (2)0.026 (2)0.0151 (18)0.0032 (15)0.0022 (14)0.0086 (16)
C200.0164 (17)0.0178 (18)0.0158 (17)0.0020 (13)0.0018 (12)0.0085 (14)
C210.0177 (17)0.0222 (19)0.0159 (17)0.0002 (13)0.0010 (12)0.0104 (15)
C220.0220 (18)0.0214 (19)0.0141 (17)0.0015 (14)0.0001 (13)0.0053 (15)
C230.0172 (17)0.0188 (18)0.0214 (19)0.0019 (13)0.0044 (13)0.0090 (15)
C240.0242 (19)0.022 (2)0.0166 (18)0.0059 (14)0.0041 (13)0.0098 (15)
C250.0191 (18)0.0208 (19)0.0175 (18)0.0030 (13)0.0026 (13)0.0088 (15)
C260.041 (2)0.020 (2)0.026 (2)0.0015 (16)0.0005 (16)0.0093 (17)
C270.0255 (19)0.025 (2)0.0186 (18)0.0052 (15)0.0018 (14)0.0091 (16)
C280.0168 (17)0.0217 (19)0.0164 (17)0.0005 (13)0.0011 (12)0.0114 (15)
C290.0163 (17)0.0191 (18)0.0134 (17)0.0006 (13)0.0007 (12)0.0087 (14)
C300.0173 (17)0.0181 (18)0.0140 (17)0.0005 (13)0.0007 (12)0.0076 (14)
C310.0192 (17)0.0186 (18)0.0145 (17)0.0020 (13)0.0002 (12)0.0074 (14)
C320.0185 (18)0.0213 (19)0.0194 (18)0.0014 (14)0.0018 (13)0.0107 (15)
C330.0227 (19)0.025 (2)0.0186 (18)0.0003 (14)0.0018 (13)0.0119 (16)
C340.0203 (18)0.024 (2)0.0162 (18)0.0029 (14)0.0016 (13)0.0062 (15)
C350.0260 (19)0.0165 (18)0.0218 (19)0.0002 (14)0.0017 (14)0.0077 (15)
C360.0244 (19)0.023 (2)0.0164 (18)0.0019 (14)0.0041 (13)0.0095 (15)
C370.0251 (19)0.023 (2)0.0220 (19)0.0058 (15)0.0020 (14)0.0099 (16)
C380.032 (2)0.031 (2)0.0171 (19)0.0004 (16)0.0031 (15)0.0059 (17)
C390.0180 (17)0.0158 (17)0.0152 (17)0.0017 (13)0.0035 (12)0.0082 (14)
C400.0199 (18)0.0210 (19)0.0159 (17)0.0017 (14)0.0016 (13)0.0081 (15)
C410.0218 (18)0.0171 (18)0.0205 (18)0.0005 (13)0.0020 (13)0.0087 (15)
C420.0193 (18)0.0208 (19)0.0223 (19)0.0045 (13)0.0060 (13)0.0131 (16)
C430.0181 (17)0.027 (2)0.0188 (18)0.0031 (14)0.0032 (13)0.0139 (16)
C440.0180 (17)0.0181 (18)0.0185 (18)0.0002 (13)0.0035 (13)0.0087 (15)
C450.0266 (19)0.0191 (19)0.025 (2)0.0012 (14)0.0038 (14)0.0139 (16)
C460.029 (2)0.023 (2)0.0215 (19)0.0018 (15)0.0043 (14)0.0097 (16)
C470.0156 (17)0.0231 (19)0.0147 (17)0.0012 (13)0.0005 (12)0.0108 (15)
C480.0187 (18)0.0224 (19)0.0206 (19)0.0007 (14)0.0021 (13)0.0105 (15)
C490.0213 (18)0.0219 (19)0.0188 (18)0.0044 (14)0.0003 (13)0.0076 (15)
C500.0208 (18)0.0185 (18)0.0229 (19)0.0013 (14)0.0022 (13)0.0103 (16)
C510.0234 (19)0.0200 (19)0.0227 (19)0.0000 (14)0.0022 (14)0.0144 (16)
C520.0187 (18)0.0202 (18)0.0150 (17)0.0001 (13)0.0007 (13)0.0086 (15)
C530.0214 (19)0.026 (2)0.0218 (19)0.0024 (14)0.0015 (14)0.0117 (16)
C540.038 (2)0.018 (2)0.026 (2)0.0004 (16)0.0031 (16)0.0110 (17)
Geometric parameters (Å, º) top
N1—C31.345 (4)C26—H26A0.9800
N1—C11.346 (4)C26—H26B0.9800
N2—C21.341 (4)C26—H26C0.9800
N2—C11.343 (4)C27—H27A0.9800
N3—C21.344 (4)C27—H27B0.9800
N3—C31.347 (4)C27—H27C0.9800
N4—C281.338 (4)C28—C311.483 (5)
N4—C291.338 (4)C29—C471.478 (5)
N5—C301.344 (4)C30—C391.489 (4)
N5—C291.350 (4)C31—C361.398 (5)
N6—C301.337 (4)C31—C321.415 (4)
N6—C281.347 (4)C32—C331.403 (5)
C1—C41.483 (5)C32—C371.512 (4)
C2—C121.487 (5)C33—C341.394 (5)
C3—C201.484 (5)C33—H330.9500
C4—C91.403 (5)C34—C351.395 (5)
C4—C51.412 (5)C34—C381.504 (5)
C5—C61.399 (5)C35—C361.390 (5)
C5—C101.513 (5)C35—H350.9500
C6—C71.391 (5)C36—H360.9500
C6—H60.9500C37—H37A0.9800
C7—C81.397 (5)C37—H37B0.9800
C7—C111.506 (5)C37—H37C0.9800
C8—C91.383 (5)C38—H38A0.9800
C8—H80.9500C38—H38B0.9800
C9—H90.9500C38—H38C0.9800
C10—H10A0.9800C39—C441.399 (4)
C10—H10B0.9800C39—C401.403 (4)
C10—H10C0.9800C40—C411.388 (5)
C11—H11A0.9800C40—H400.9500
C11—H11B0.9800C41—C421.389 (5)
C11—H11C0.9800C41—H410.9500
C12—C131.398 (4)C42—C431.388 (5)
C12—C171.408 (4)C42—C451.514 (4)
C13—C141.392 (5)C43—C441.399 (4)
C13—H130.9500C43—H430.9500
C14—C151.388 (5)C44—C461.519 (4)
C14—H140.9500C45—H45A0.9800
C15—C161.393 (5)C45—H45B0.9800
C15—C181.506 (5)C45—H45C0.9800
C16—C171.398 (5)C46—H46A0.9800
C16—H160.9500C46—H46B0.9800
C17—C191.513 (5)C46—H46C0.9800
C18—H18A0.9800C47—C481.405 (5)
C18—H18B0.9800C47—C521.409 (4)
C18—H18C0.9800C48—C491.403 (5)
C19—H19A0.9800C48—C531.519 (5)
C19—H19B0.9800C49—C501.387 (5)
C19—H19C0.9800C49—H490.9500
C20—C211.402 (4)C50—C511.399 (5)
C20—C251.411 (5)C50—C541.510 (5)
C21—C221.389 (5)C51—C521.379 (5)
C21—H210.9500C51—H510.9500
C22—C231.401 (5)C52—H520.9500
C22—H220.9500C53—H53A0.9800
C23—C241.386 (5)C53—H53B0.9800
C23—C261.515 (5)C53—H53C0.9800
C24—C251.404 (5)C54—H54A0.9800
C24—H240.9500C54—H54B0.9800
C25—C271.514 (4)C54—H54C0.9800
C3—N1—C1115.2 (3)C25—C27—H27C109.5
C2—N2—C1115.5 (3)H27A—C27—H27C109.5
C2—N3—C3115.6 (3)H27B—C27—H27C109.5
C28—N4—C29116.5 (3)N4—C28—N6124.0 (3)
C30—N5—C29114.8 (3)N4—C28—C31118.2 (3)
C30—N6—C28115.1 (3)N6—C28—C31117.6 (3)
N2—C1—N1124.8 (3)N4—C29—N5124.0 (3)
N2—C1—C4116.5 (3)N4—C29—C47116.9 (3)
N1—C1—C4118.7 (3)N5—C29—C47119.1 (3)
N2—C2—N3124.4 (3)N6—C30—N5125.5 (3)
N2—C2—C12117.3 (3)N6—C30—C39117.2 (3)
N3—C2—C12118.1 (3)N5—C30—C39117.3 (3)
N1—C3—N3124.5 (3)C36—C31—C32118.8 (3)
N1—C3—C20119.3 (3)C36—C31—C28117.5 (3)
N3—C3—C20116.2 (3)C32—C31—C28123.6 (3)
C9—C4—C5119.2 (3)C33—C32—C31117.9 (3)
C9—C4—C1117.0 (3)C33—C32—C37117.3 (3)
C5—C4—C1123.7 (3)C31—C32—C37124.7 (3)
C6—C5—C4117.8 (3)C34—C33—C32123.0 (3)
C6—C5—C10117.1 (3)C34—C33—H33118.5
C4—C5—C10125.1 (3)C32—C33—H33118.5
C7—C6—C5123.0 (3)C33—C34—C35118.2 (3)
C7—C6—H6118.5C33—C34—C38120.8 (3)
C5—C6—H6118.5C35—C34—C38121.0 (3)
C6—C7—C8118.5 (3)C36—C35—C34119.9 (3)
C6—C7—C11120.8 (3)C36—C35—H35120.0
C8—C7—C11120.7 (3)C34—C35—H35120.0
C9—C8—C7119.9 (3)C35—C36—C31122.0 (3)
C9—C8—H8120.1C35—C36—H36119.0
C7—C8—H8120.1C31—C36—H36119.0
C8—C9—C4121.6 (3)C32—C37—H37A109.5
C8—C9—H9119.2C32—C37—H37B109.5
C4—C9—H9119.2H37A—C37—H37B109.5
C5—C10—H10A109.5C32—C37—H37C109.5
C5—C10—H10B109.5H37A—C37—H37C109.5
H10A—C10—H10B109.5H37B—C37—H37C109.5
C5—C10—H10C109.5C34—C38—H38A109.5
H10A—C10—H10C109.5C34—C38—H38B109.5
H10B—C10—H10C109.5H38A—C38—H38B109.5
C7—C11—H11A109.5C34—C38—H38C109.5
C7—C11—H11B109.5H38A—C38—H38C109.5
H11A—C11—H11B109.5H38B—C38—H38C109.5
C7—C11—H11C109.5C44—C39—C40118.9 (3)
H11A—C11—H11C109.5C44—C39—C30124.6 (3)
H11B—C11—H11C109.5C40—C39—C30116.5 (3)
C13—C12—C17119.1 (3)C41—C40—C39121.5 (3)
C13—C12—C2116.9 (3)C41—C40—H40119.3
C17—C12—C2123.9 (3)C39—C40—H40119.3
C14—C13—C12121.4 (3)C40—C41—C42120.0 (3)
C14—C13—H13119.3C40—C41—H41120.0
C12—C13—H13119.3C42—C41—H41120.0
C15—C14—C13120.3 (3)C43—C42—C41118.4 (3)
C15—C14—H14119.9C43—C42—C45120.4 (3)
C13—C14—H14119.8C41—C42—C45121.2 (3)
C14—C15—C16117.8 (3)C42—C43—C44122.7 (3)
C14—C15—C18121.1 (3)C42—C43—H43118.6
C16—C15—C18121.1 (3)C44—C43—H43118.6
C15—C16—C17123.4 (3)C39—C44—C43118.4 (3)
C15—C16—H16118.3C39—C44—C46124.8 (3)
C17—C16—H16118.3C43—C44—C46116.8 (3)
C16—C17—C12117.8 (3)C42—C45—H45A109.5
C16—C17—C19117.6 (3)C42—C45—H45B109.5
C12—C17—C19124.6 (3)H45A—C45—H45B109.5
C15—C18—H18A109.5C42—C45—H45C109.5
C15—C18—H18B109.5H45A—C45—H45C109.5
H18A—C18—H18B109.5H45B—C45—H45C109.5
C15—C18—H18C109.5C44—C46—H46A109.5
H18A—C18—H18C109.5C44—C46—H46B109.5
H18B—C18—H18C109.5H46A—C46—H46B109.5
C17—C19—H19A109.5C44—C46—H46C109.5
C17—C19—H19B109.5H46A—C46—H46C109.5
H19A—C19—H19B109.5H46B—C46—H46C109.5
C17—C19—H19C109.5C48—C47—C52118.8 (3)
H19A—C19—H19C109.5C48—C47—C29124.5 (3)
H19B—C19—H19C109.5C52—C47—C29116.7 (3)
C21—C20—C25118.8 (3)C49—C48—C47118.0 (3)
C21—C20—C3117.1 (3)C49—C48—C53116.8 (3)
C25—C20—C3124.0 (3)C47—C48—C53125.1 (3)
C22—C21—C20122.1 (3)C50—C49—C48123.4 (3)
C22—C21—H21119.0C50—C49—H49118.3
C20—C21—H21119.0C48—C49—H49118.3
C21—C22—C23119.7 (3)C49—C50—C51117.6 (3)
C21—C22—H22120.2C49—C50—C54121.5 (3)
C23—C22—H22120.2C51—C50—C54121.0 (3)
C24—C23—C22118.2 (3)C52—C51—C50120.6 (3)
C24—C23—C26121.6 (3)C52—C51—H51119.7
C22—C23—C26120.2 (3)C50—C51—H51119.7
C23—C24—C25123.4 (3)C51—C52—C47121.5 (3)
C23—C24—H24118.3C51—C52—H52119.2
C25—C24—H24118.3C47—C52—H52119.2
C24—C25—C20117.8 (3)C48—C53—H53A109.5
C24—C25—C27116.9 (3)C48—C53—H53B109.5
C20—C25—C27125.3 (3)H53A—C53—H53B109.5
C23—C26—H26A109.5C48—C53—H53C109.5
C23—C26—H26B109.5H53A—C53—H53C109.5
H26A—C26—H26B109.5H53B—C53—H53C109.5
C23—C26—H26C109.5C50—C54—H54A109.5
H26A—C26—H26C109.5C50—C54—H54B109.5
H26B—C26—H26C109.5H54A—C54—H54B109.5
C25—C27—H27A109.5C50—C54—H54C109.5
C25—C27—H27B109.5H54A—C54—H54C109.5
H27A—C27—H27B109.5H54B—C54—H54C109.5
C2—N2—C1—N11.1 (5)C29—N4—C28—N61.7 (5)
C2—N2—C1—C4178.3 (3)C29—N4—C28—C31173.6 (3)
C3—N1—C1—N21.7 (5)C30—N6—C28—N40.6 (5)
C3—N1—C1—C4178.9 (3)C30—N6—C28—C31174.8 (3)
C1—N2—C2—N30.9 (5)C28—N4—C29—N51.4 (5)
C1—N2—C2—C12175.1 (3)C28—N4—C29—C47179.1 (3)
C3—N3—C2—N21.9 (5)C30—N5—C29—N40.0 (4)
C3—N3—C2—C12174.0 (3)C30—N5—C29—C47179.5 (3)
C1—N1—C3—N30.5 (5)C28—N6—C30—N51.0 (5)
C1—N1—C3—C20178.5 (3)C28—N6—C30—C39178.4 (3)
C2—N3—C3—N11.1 (5)C29—N5—C30—N61.2 (5)
C2—N3—C3—C20179.8 (3)C29—N5—C30—C39178.6 (3)
N2—C1—C4—C928.5 (4)N4—C28—C31—C36154.1 (3)
N1—C1—C4—C9148.9 (3)N6—C28—C31—C3621.6 (5)
N2—C1—C4—C5151.8 (3)N4—C28—C31—C3221.5 (5)
N1—C1—C4—C530.8 (5)N6—C28—C31—C32162.8 (3)
C9—C4—C5—C62.2 (5)C36—C31—C32—C334.2 (5)
C1—C4—C5—C6177.5 (3)C28—C31—C32—C33171.3 (3)
C9—C4—C5—C10175.7 (3)C36—C31—C32—C37174.0 (3)
C1—C4—C5—C104.6 (5)C28—C31—C32—C3710.5 (5)
C4—C5—C6—C70.2 (5)C31—C32—C33—C341.1 (5)
C10—C5—C6—C7177.9 (3)C37—C32—C33—C34177.2 (3)
C5—C6—C7—C81.8 (5)C32—C33—C34—C352.4 (5)
C5—C6—C7—C11176.8 (3)C32—C33—C34—C38177.3 (3)
C6—C7—C8—C91.7 (5)C33—C34—C35—C362.6 (5)
C11—C7—C8—C9176.8 (3)C38—C34—C35—C36177.0 (3)
C7—C8—C9—C40.3 (5)C34—C35—C36—C310.5 (5)
C5—C4—C9—C82.3 (5)C32—C31—C36—C354.0 (5)
C1—C4—C9—C8177.5 (3)C28—C31—C36—C35171.8 (3)
N2—C2—C12—C1323.1 (4)N6—C30—C39—C44151.5 (3)
N3—C2—C12—C13153.1 (3)N5—C30—C39—C4430.9 (5)
N2—C2—C12—C17160.4 (3)N6—C30—C39—C4030.1 (4)
N3—C2—C12—C1723.3 (5)N5—C30—C39—C40147.5 (3)
C17—C12—C13—C143.9 (5)C44—C39—C40—C413.4 (5)
C2—C12—C13—C14172.8 (3)C30—C39—C40—C41175.1 (3)
C12—C13—C14—C150.7 (5)C39—C40—C41—C421.2 (5)
C13—C14—C15—C162.6 (5)C40—C41—C42—C432.1 (5)
C13—C14—C15—C18177.5 (3)C40—C41—C42—C45175.9 (3)
C14—C15—C16—C172.8 (5)C41—C42—C43—C443.2 (5)
C18—C15—C16—C17177.4 (3)C45—C42—C43—C44174.8 (3)
C15—C16—C17—C120.4 (5)C40—C39—C44—C432.3 (5)
C15—C16—C17—C19177.7 (3)C30—C39—C44—C43176.1 (3)
C13—C12—C17—C163.6 (5)C40—C39—C44—C46176.4 (3)
C2—C12—C17—C16172.7 (3)C30—C39—C44—C465.2 (5)
C13—C12—C17—C19174.3 (3)C42—C43—C44—C391.0 (5)
C2—C12—C17—C199.3 (5)C42—C43—C44—C46179.8 (3)
N1—C3—C20—C21158.5 (3)N4—C29—C47—C48159.9 (3)
N3—C3—C20—C2120.7 (4)N5—C29—C47—C4820.6 (5)
N1—C3—C20—C2520.3 (5)N4—C29—C47—C5220.1 (4)
N3—C3—C20—C25160.5 (3)N5—C29—C47—C52159.5 (3)
C25—C20—C21—C221.6 (5)C52—C47—C48—C492.3 (5)
C3—C20—C21—C22177.2 (3)C29—C47—C48—C49177.7 (3)
C20—C21—C22—C230.1 (5)C52—C47—C48—C53176.0 (3)
C21—C22—C23—C241.5 (5)C29—C47—C48—C533.9 (5)
C21—C22—C23—C26177.2 (3)C47—C48—C49—C500.3 (5)
C22—C23—C24—C251.2 (5)C53—C48—C49—C50178.2 (3)
C26—C23—C24—C25177.5 (3)C48—C49—C50—C511.7 (5)
C23—C24—C25—C200.6 (5)C48—C49—C50—C54177.3 (3)
C23—C24—C25—C27177.4 (3)C49—C50—C51—C521.7 (5)
C21—C20—C25—C241.9 (5)C54—C50—C51—C52177.3 (3)
C3—C20—C25—C24176.9 (3)C50—C51—C52—C470.3 (5)
C21—C20—C25—C27175.8 (3)C48—C47—C52—C512.4 (5)
C3—C20—C25—C275.4 (5)C29—C47—C52—C51177.7 (3)
Hydrogen-bond geometry (Å, º) top
Cg1–Cg4 are the centroids of the C39–C44, C31–C36, C12–C17 and C4–C9 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11B···Cg1i0.982.973.777 (4)140
C18—H18B···Cg2ii0.982.913.688 (4)137
C38—H38C···Cg3iii0.982.843.756 (4)155
C45—H45B···Cg4iv0.982.773.596 (4)142
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z+2; (iii) x+1, y+1, z+2; (iv) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC27H27N3
Mr393.52
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.4663 (4), 15.0789 (13), 19.7266 (12)
α, β, γ (°)109.016 (7), 90.949 (5), 93.717 (6)
V3)2093.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.15 × 0.05
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.978, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
14777, 9605, 5518
Rint0.058
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.085, 0.222, 1.04
No. of reflections9597
No. of parameters554
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.39

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), Qmol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1–Cg4 are the centroids of the C39–C44, C31–C36, C12–C17 and C4–C9 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11B···Cg1i0.982.973.777 (4)140
C18—H18B···Cg2ii0.982.913.688 (4)137
C38—H38C···Cg3iii0.982.843.756 (4)155
C45—H45B···Cg4iv0.982.773.596 (4)142
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z+2; (iii) x+1, y+1, z+2; (iv) x+1, y+1, z+1.
 

Footnotes

Additional correspondence author, e-mail: cesyyy@mail.sysu.edu.cn.

Acknowledgements

We thank the Opening Laboratory Fund of Sun Yat-sen University. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

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Volume 68| Part 5| May 2012| Pages o1463-o1464
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