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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages o521-o522

Crystal structure of 11-[4-(hex­yl­oxy)phen­yl]-1,2,4-triazolo[4,3-a][1,10]phenanthroline

aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: detert@uni-mainz.de

Edited by M. Nieger, University of Helsinki, Finland (Received 11 May 2015; accepted 23 June 2015; online 27 June 2015)

The title compound, C25H24N4O, was prepared from 2-chloro­phenanthroline and hexyl­oxyphenyl­tetra­zole. The main difference between the two independent mol­ecules (A and B) in the asymmetric unit is the orientation of the all-anti-configured hex­yloxy chain: in A the C—O—C—C torsion angle is 175.9 (2)° whereas it is −88.3 (3)° in B. The benzene substitution in the bay of the triazolophenanthroline results in a helical distorsion of the heterocyclic core, the dihedral angles between the mean planes formed by quinoline and benzotriazole ring systems are 13.73 (9) for mol­ecule A and 14.87 (8)° for B. The dihedral angles between the triazole ring and the attached benzene ring are 45.87 (15) in A and 53.93 (14)° in B. The angular annulation of four rings and the benzene substituent results in a helical distortion of the aromatic framework. The crystal is formed from layers composed of centrosymmetric pairs of A2, B2 mol­ecules with inter­digitating alkyl chains.

1. Related literature

For structures of 1,2,4-triazolo annulated diazines, see: Preis et al. (2011a[Preis, J., Schollmeyer, D. & Detert, H. (2011a). Acta Cryst. E67, o987.],b[Preis, J., Schollmeyer, D. & Detert, H. (2011b). Acta Cryst. E67, o2551.]); for a triazolo­thia­zole, see: Schollmeyer & Detert (2014[Schollmeyer, D. & Detert, H. (2014). Acta Cryst. E70, o247.]); for threefold triazoloannulated triazines, see: Cristiano et al. (2008[Cristiano, R., Gallardo, H., Bortoluzzi, A. J., Bechtold, I. H., Campos, C. E. M. & Longo, R. L. (2008). Chem. Commun. pp. 5134.]); Herget et al. (2013[Herget, K., Schollmeyer, D. & Detert, H. (2013). Acta Cryst. E69, o365-o366.]); Glang et al. (2014[Glang, S., Rieth, T., Borchmann, D., Fortunati, I., Signorini, R. & Detert, H. (2014). Eur. J. Org. Chem. pp. 3116-3126.]); Rieth et al. (2014[Rieth, T., Marszalek, T., Pisula, W. & Detert, H. (2014). Chem. Eur. J. 20, 5000-5006.]). For structures of aza­helicenes, see: Caronna et al. (2012[Caronna, T., Castiglione, F., Famulari, A., Fontana, F., Malpezzi, L., Mele, A., Mendola, D. & Sora, I. N. (2012). Molecules, 17, 463-479.]); Upadhyay et al. (2014[Upadhyay, G. M., Talele, H. R., Sahoo, S. & Bedekar, A. V. (2014). Tetrahedron Lett. 55, 5394-5399.]). Synthesis: for chloro­phenanthroline as starting material, see: Lewis & O'Donoghue (1980[Lewis, J. & O'Donoghue, T. D. (1980). J. Chem. Soc. Dalton Trans. pp. 736-742.]); for 1,2,4-triazoloannulation via tetra­zoles, see: Huisgen et al. (1960[Huisgen, R., Sauer, J. & Seidel, M. (1960). Chem. Ber. 93, 2885-2891.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C25H24N4O

  • Mr = 396.48

  • Monoclinic, P 21 /c

  • a = 9.746 (3) Å

  • b = 36.787 (5) Å

  • c = 12.174 (3) Å

  • β = 106.412 (12)°

  • V = 4186.6 (17) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.62 mm−1

  • T = 193 K

  • 0.34 × 0.23 × 0.23 mm

2.2. Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • 8415 measured reflections

  • 7934 independent reflections

  • 5140 reflections with I > 2σ(I)

  • Rint = 0.051

  • 3 standard reflections every 60 min intensity decay: 5%

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.170

  • S = 1.02

  • 7934 reflections

  • 543 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.31 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971[Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2014.

Supporting information


Chemical context top

The title compound, C25H24N4O, was prepared as part of a larger study on triazolo-annulated azines, see Glang et al. (2014), Rieth et al. (2014), Preis et al. (2011a). This triazolophenanthroline was prepared according to Huisgen (Huisgen et al. 1960) via nucleophilic substitution, cyclo­elimination/ring closure from 2-chloro­phenanthroline (Lewis & O'Donoghue, 1980) and hexyl­oxyphenyl tetra­zole. This is an efficient method for the preparation of triazolo-annulated azines.

Structural commentary top

The monoclinic unit cell is composed of two different molecules A, B of the title compound.The main difference between A and B is the orientation of the all-anti configured hexyl­oxy chain: in A the torsion angle C21A—O24A—C25A—C26A is 175.9 (2)° wheras C21B—O24B—C25B—C26B is -88.3 (3)°. The phenyl substitution in the bay of the triazolophenanthroline results in a helical distorsion of the heterocyclic core, the dihedral angles between the mean planes formed by quinoline and benzotriazole are 13.73 (9) ° for molecule A and 14.87 (8) ° for B. The dihedral angles between the triazole ring and the attached phenyl ring are 45.87 (15) ° (A) and 53.93 (14) ° (B).

Supra­molecular features top

The crystal is formed from layers composed of centrosymmetric pairs of A2, B2 and the alkyl chains are inter­digitating.

Synthesis and crystallization top

The title compound was prepared by refluxing a solution of 5-(4-hexyl­oxyphenyl)­tetra­zole (150 mg, 0.61 mmol) and 2-chloro-[1,10]phenanthroline ( 131 mg, 0.61 mmol), prepared according to Lewis & O'Donoghue (Lewis & O'Donoghue, 1980) in xylenes / pyridine (7mL, 5/1) for 8 d. The solvents were evaporated and the residue purified via chromatography on silica gel using ethyl acetate / toluene (2/1) with 1% tri­ethyl­amine as an eluent. Yield: 128 mg (53%) of a brownish solid with m. p.= 419 K. Single crystals were obtained by slow evaporation of a saturated solution in chloro­form/ethanol (5/1).

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1. Hydrogen atoms attached to carbons were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.98–0.99 Å (sp3 C-atom). All H atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq of the parent atom).

Related literature top

For structures of 1,2,4-triazolo annulated diazines, see: Preis et al. (2011a,b); for a triazolothiazole, see: Schollmeyer & Detert (2014); for threefold triazoloannulated triazines, see: Cristiano et al. (2008); Herget et al. (2013); Glang et al. (2014); Rieth et al. (2014). For structures of azahelicenes, see: Caronna et al. (2012); Upadhyay et al. (2014). Synthesis: for chlorophenanthroline as starting material, see: Lewis & O'Donoghue (1980); for 1,2,4-triazoloannulation via tetrazoles, see: Huisgen et al. (1960).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of the packing diagram. Molecule B coloured in red. View along the c axis.
11-[4-(Hexyloxy)phenyl]-1,2,4-triazolo[4,3-a][1,10]phenanthroline top
Crystal data top
C25H24N4OF(000) = 1680
Mr = 396.48Dx = 1.258 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 9.746 (3) ÅCell parameters from 25 reflections
b = 36.787 (5) Åθ = 25–38°
c = 12.174 (3) ŵ = 0.62 mm1
β = 106.412 (12)°T = 193 K
V = 4186.6 (17) Å3Block, colourless
Z = 80.34 × 0.23 × 0.23 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.051
Radiation source: rotating anodeθmax = 70.2°, θmin = 2.4°
Graphite monochromatorh = 110
ω/2θ scansk = 044
8415 measured reflectionsl = 1414
7934 independent reflections3 standard reflections every 60 min
5140 reflections with I > 2σ(I) intensity decay: 5%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.170 w = 1/[σ2(Fo2) + (0.0793P)2 + 0.8479P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
7934 reflectionsΔρmax = 0.41 e Å3
543 parametersΔρmin = 0.30 e Å3
Crystal data top
C25H24N4OV = 4186.6 (17) Å3
Mr = 396.48Z = 8
Monoclinic, P21/cCu Kα radiation
a = 9.746 (3) ŵ = 0.62 mm1
b = 36.787 (5) ÅT = 193 K
c = 12.174 (3) Å0.34 × 0.23 × 0.23 mm
β = 106.412 (12)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.051
8415 measured reflections3 standard reflections every 60 min
7934 independent reflections intensity decay: 5%
5140 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.170H-atom parameters constrained
S = 1.02Δρmax = 0.41 e Å3
7934 reflectionsΔρmin = 0.30 e Å3
543 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.3086 (2)0.08512 (6)0.6267 (2)0.0381 (5)
C2A0.2720 (3)0.11722 (8)0.6648 (2)0.0331 (6)
C3A0.3790 (3)0.14428 (8)0.7072 (2)0.0334 (6)
N4A0.5224 (2)0.14042 (6)0.70355 (18)0.0358 (5)
C5A0.5963 (3)0.11790 (8)0.6480 (2)0.0391 (7)
N6A0.7342 (3)0.12405 (8)0.6896 (2)0.0551 (7)
N7A0.7563 (3)0.15103 (9)0.7702 (2)0.0612 (8)
C8A0.6297 (3)0.16150 (9)0.7758 (2)0.0462 (7)
C9A0.5964 (3)0.19102 (9)0.8380 (3)0.0528 (8)
H9A0.67020.20540.88600.063*
C10A0.4585 (3)0.19833 (9)0.8279 (3)0.0461 (7)
H10A0.43400.21940.86360.055*
C11A0.3481 (3)0.17474 (8)0.7640 (2)0.0392 (6)
C12A0.2039 (3)0.18070 (8)0.7658 (2)0.0431 (7)
H12A0.18150.20210.80080.052*
C13A0.0992 (3)0.15688 (8)0.7195 (2)0.0416 (7)
H13A0.00390.16190.72050.050*
C14A0.1303 (3)0.12420 (8)0.6692 (2)0.0359 (6)
C15A0.0257 (3)0.09793 (8)0.6239 (2)0.0417 (7)
H15A0.07060.10200.62360.050*
C16A0.0623 (3)0.06658 (8)0.5803 (3)0.0441 (7)
H16A0.00790.04880.54740.053*
C17A0.2064 (3)0.06120 (8)0.5851 (3)0.0449 (7)
H17A0.23200.03890.55670.054*
C18A0.5455 (3)0.09471 (8)0.5466 (2)0.0354 (6)
C19A0.6156 (3)0.06239 (8)0.5409 (3)0.0447 (7)
H19A0.69050.05470.60520.054*
C20A0.5791 (3)0.04110 (9)0.4442 (3)0.0485 (8)
H20A0.62840.01890.44250.058*
C21A0.4708 (3)0.05184 (8)0.3494 (2)0.0402 (7)
C22A0.4013 (3)0.08460 (7)0.3532 (2)0.0373 (6)
H22A0.32760.09240.28830.045*
C23A0.4382 (3)0.10573 (8)0.4497 (2)0.0366 (6)
H23A0.39030.12820.45080.044*
O24A0.4242 (2)0.03266 (6)0.24946 (18)0.0507 (6)
C25A0.4945 (3)0.00070 (8)0.2399 (3)0.0474 (7)
H25A0.49200.01720.30360.057*
H25B0.59570.00390.24330.057*
C26A0.4169 (3)0.01768 (8)0.1266 (3)0.0483 (7)
H26A0.41760.00060.06400.058*
H26B0.31600.02220.12440.058*
C27A0.4855 (4)0.05310 (9)0.1076 (3)0.0560 (9)
H27A0.58560.04810.10810.067*
H27B0.48850.06950.17270.067*
C28A0.4121 (4)0.07244 (10)0.0013 (3)0.0618 (9)
H28A0.40750.05600.06670.074*
H28B0.31270.07800.00140.074*
C29A0.4867 (5)0.10793 (12)0.0186 (4)0.0866 (13)
H29A0.58420.10210.02260.104*
H29B0.49630.12370.04920.104*
C30A0.4130 (6)0.12808 (13)0.1203 (4)0.1080 (18)
H30A0.31910.13580.11430.162*
H30B0.46950.14950.12750.162*
H30C0.40040.11260.18780.162*
N1B0.9406 (2)0.24530 (6)0.63224 (18)0.0328 (5)
C2B0.8565 (2)0.22341 (7)0.5515 (2)0.0274 (5)
C3B0.9214 (2)0.20124 (7)0.4832 (2)0.0286 (5)
N4B1.0647 (2)0.20604 (6)0.48078 (17)0.0278 (4)
C5B1.1665 (3)0.23334 (7)0.5133 (2)0.0309 (5)
N6B1.2883 (2)0.22181 (6)0.4984 (2)0.0377 (5)
N7B1.2699 (2)0.18737 (6)0.4529 (2)0.0379 (5)
C8B1.1352 (3)0.17842 (7)0.4402 (2)0.0314 (6)
C9B1.0598 (3)0.14781 (7)0.3835 (2)0.0359 (6)
H9B1.10790.12920.35490.043*
C10B0.9179 (3)0.14563 (7)0.3709 (2)0.0367 (6)
H10B0.86440.12620.32790.044*
C11B0.8468 (3)0.17217 (7)0.4214 (2)0.0321 (6)
C12B0.6978 (3)0.16838 (8)0.4115 (2)0.0395 (6)
H12B0.64550.14890.36800.047*
C13B0.6296 (3)0.19222 (8)0.4634 (2)0.0393 (6)
H13B0.52910.19040.45090.047*
C14B0.7071 (3)0.21971 (7)0.5358 (2)0.0329 (6)
C15B0.6446 (3)0.24288 (8)0.5998 (2)0.0413 (7)
H15B0.54440.24210.58990.050*
C16B0.7283 (3)0.26637 (8)0.6758 (3)0.0443 (7)
H16B0.68710.28280.71760.053*
C17B0.8769 (3)0.26598 (8)0.6916 (2)0.0389 (6)
H17B0.93480.28150.74840.047*
C18B1.1488 (2)0.27117 (7)0.5436 (2)0.0296 (5)
C19B1.2452 (3)0.28641 (8)0.6394 (2)0.0377 (6)
H19B1.31930.27190.68660.045*
C20B1.2332 (3)0.32247 (8)0.6658 (2)0.0429 (7)
H20B1.29880.33270.73170.052*
C21B1.1261 (3)0.34398 (7)0.5969 (2)0.0387 (6)
C22B1.0320 (3)0.32928 (7)0.4996 (2)0.0355 (6)
H22B0.95980.34400.45090.043*
C23B1.0443 (3)0.29311 (7)0.4743 (2)0.0326 (6)
H23B0.97960.28300.40780.039*
O24B1.1212 (3)0.37890 (6)0.63403 (19)0.0546 (6)
C25B1.0265 (4)0.40429 (8)0.5614 (3)0.0552 (9)
H25C0.99610.42260.60920.066*
H25D0.94000.39130.51600.066*
C26B1.0954 (4)0.42309 (10)0.4818 (3)0.0566 (9)
H26C1.12320.40480.43250.068*
H26D1.18360.43540.52720.068*
C27B0.9968 (4)0.45097 (9)0.4066 (3)0.0592 (9)
H27C0.92210.43800.34750.071*
H27D0.94830.46490.45430.071*
C28B1.0725 (4)0.47745 (9)0.3474 (3)0.0576 (9)
H28C1.14410.49130.40640.069*
H28D1.12440.46350.30210.069*
C29B0.9715 (4)0.50394 (10)0.2689 (3)0.0656 (10)
H29C0.90170.49020.20830.079*
H29D0.91770.51750.31350.079*
C30B1.0493 (5)0.53075 (11)0.2134 (4)0.0859 (14)
H30D1.12580.54250.27260.129*
H30E0.98180.54920.17190.129*
H30F1.09050.51790.15980.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0341 (12)0.0421 (13)0.0419 (13)0.0052 (10)0.0169 (10)0.0024 (11)
C2A0.0292 (13)0.0469 (16)0.0260 (13)0.0084 (12)0.0122 (10)0.0083 (11)
C3A0.0258 (13)0.0474 (16)0.0296 (13)0.0075 (12)0.0118 (10)0.0063 (12)
N4A0.0250 (11)0.0503 (14)0.0337 (12)0.0038 (10)0.0108 (9)0.0028 (10)
C5A0.0223 (12)0.0589 (18)0.0376 (15)0.0078 (12)0.0107 (11)0.0016 (13)
N6A0.0259 (12)0.088 (2)0.0518 (16)0.0034 (13)0.0112 (11)0.0151 (15)
N7A0.0275 (13)0.098 (2)0.0566 (17)0.0048 (14)0.0095 (12)0.0279 (16)
C8A0.0278 (14)0.070 (2)0.0402 (16)0.0036 (14)0.0089 (12)0.0121 (15)
C9A0.0435 (17)0.068 (2)0.0461 (18)0.0057 (16)0.0114 (14)0.0166 (16)
C10A0.0460 (17)0.0547 (19)0.0404 (16)0.0033 (14)0.0168 (14)0.0081 (14)
C11A0.0380 (15)0.0485 (17)0.0343 (14)0.0060 (13)0.0158 (12)0.0021 (13)
C12A0.0448 (17)0.0503 (17)0.0397 (16)0.0137 (14)0.0209 (13)0.0005 (14)
C13A0.0325 (15)0.0553 (18)0.0421 (16)0.0124 (13)0.0190 (12)0.0073 (14)
C14A0.0269 (13)0.0495 (16)0.0338 (14)0.0080 (12)0.0128 (11)0.0091 (12)
C15A0.0276 (14)0.0588 (19)0.0433 (16)0.0025 (13)0.0173 (12)0.0101 (14)
C16A0.0358 (15)0.0516 (18)0.0467 (17)0.0044 (13)0.0146 (13)0.0066 (14)
C17A0.0440 (17)0.0439 (17)0.0520 (18)0.0036 (14)0.0219 (14)0.0020 (14)
C18A0.0235 (12)0.0498 (16)0.0361 (14)0.0059 (12)0.0138 (11)0.0008 (12)
C19A0.0336 (15)0.0588 (19)0.0404 (16)0.0165 (14)0.0085 (12)0.0025 (14)
C20A0.0431 (17)0.0523 (19)0.0485 (18)0.0200 (14)0.0102 (14)0.0013 (15)
C21A0.0360 (15)0.0443 (16)0.0407 (16)0.0049 (12)0.0116 (12)0.0026 (13)
C22A0.0299 (14)0.0400 (15)0.0398 (15)0.0063 (12)0.0062 (11)0.0050 (12)
C23A0.0281 (13)0.0406 (15)0.0445 (16)0.0052 (11)0.0159 (12)0.0000 (13)
O24A0.0531 (13)0.0459 (12)0.0474 (12)0.0149 (10)0.0050 (10)0.0077 (10)
C25A0.0543 (18)0.0430 (17)0.0474 (17)0.0090 (14)0.0185 (14)0.0008 (14)
C26A0.0490 (18)0.0460 (18)0.0493 (18)0.0030 (14)0.0129 (14)0.0024 (14)
C27A0.070 (2)0.0520 (19)0.0453 (18)0.0074 (17)0.0156 (17)0.0043 (15)
C28A0.070 (2)0.056 (2)0.062 (2)0.0069 (18)0.0226 (19)0.0114 (17)
C29A0.108 (4)0.076 (3)0.067 (3)0.002 (3)0.009 (3)0.016 (2)
C30A0.133 (5)0.098 (4)0.087 (3)0.013 (3)0.023 (3)0.036 (3)
N1B0.0279 (11)0.0406 (13)0.0321 (11)0.0008 (9)0.0120 (9)0.0025 (10)
C2B0.0236 (12)0.0303 (13)0.0306 (13)0.0004 (10)0.0115 (10)0.0026 (10)
C3B0.0223 (12)0.0351 (13)0.0304 (13)0.0001 (10)0.0105 (10)0.0028 (11)
N4B0.0196 (10)0.0335 (11)0.0320 (11)0.0004 (8)0.0100 (8)0.0002 (9)
C5B0.0210 (12)0.0381 (14)0.0344 (13)0.0014 (11)0.0092 (10)0.0014 (11)
N6B0.0230 (11)0.0446 (13)0.0475 (14)0.0012 (10)0.0134 (10)0.0035 (11)
N7B0.0278 (11)0.0421 (13)0.0454 (14)0.0047 (10)0.0129 (10)0.0038 (11)
C8B0.0287 (13)0.0369 (14)0.0306 (13)0.0067 (11)0.0115 (10)0.0003 (11)
C9B0.0374 (14)0.0340 (14)0.0388 (15)0.0041 (12)0.0149 (12)0.0025 (12)
C10B0.0392 (15)0.0345 (14)0.0369 (14)0.0034 (12)0.0117 (12)0.0055 (12)
C11B0.0312 (13)0.0334 (14)0.0337 (14)0.0021 (11)0.0123 (11)0.0000 (11)
C12B0.0310 (14)0.0456 (16)0.0431 (16)0.0102 (12)0.0122 (12)0.0054 (13)
C13B0.0226 (13)0.0521 (17)0.0451 (16)0.0067 (12)0.0125 (11)0.0030 (13)
C14B0.0233 (12)0.0404 (15)0.0369 (14)0.0017 (11)0.0114 (11)0.0004 (12)
C15B0.0271 (14)0.0523 (18)0.0492 (17)0.0027 (12)0.0186 (12)0.0001 (14)
C16B0.0399 (16)0.0515 (18)0.0476 (17)0.0040 (14)0.0222 (14)0.0098 (14)
C17B0.0383 (15)0.0428 (16)0.0388 (15)0.0030 (13)0.0160 (12)0.0065 (13)
C18B0.0213 (12)0.0371 (14)0.0330 (13)0.0035 (10)0.0119 (10)0.0004 (11)
C19B0.0280 (13)0.0440 (16)0.0391 (15)0.0037 (12)0.0062 (11)0.0018 (12)
C20B0.0370 (15)0.0488 (17)0.0374 (15)0.0100 (13)0.0015 (12)0.0055 (13)
C21B0.0451 (16)0.0339 (14)0.0394 (15)0.0044 (12)0.0156 (13)0.0037 (12)
C22B0.0325 (14)0.0369 (15)0.0357 (14)0.0039 (11)0.0074 (11)0.0022 (12)
C23B0.0270 (13)0.0426 (15)0.0282 (13)0.0042 (11)0.0078 (10)0.0036 (11)
O24B0.0715 (15)0.0361 (11)0.0516 (13)0.0002 (11)0.0098 (11)0.0075 (10)
C25B0.069 (2)0.0391 (17)0.062 (2)0.0068 (16)0.0263 (18)0.0044 (15)
C26B0.056 (2)0.059 (2)0.056 (2)0.0071 (16)0.0175 (16)0.0039 (16)
C27B0.055 (2)0.058 (2)0.064 (2)0.0063 (17)0.0142 (17)0.0074 (18)
C28B0.070 (2)0.057 (2)0.0460 (18)0.0054 (18)0.0161 (17)0.0057 (16)
C29B0.073 (2)0.063 (2)0.058 (2)0.0058 (19)0.0131 (18)0.0108 (18)
C30B0.120 (4)0.073 (3)0.070 (3)0.012 (3)0.037 (3)0.006 (2)
Geometric parameters (Å, º) top
N1A—C17A1.318 (4)N1B—C17B1.319 (3)
N1A—C2A1.353 (3)N1B—C2B1.353 (3)
C2A—C14A1.421 (3)C2B—C14B1.421 (3)
C2A—C3A1.428 (4)C2B—C3B1.433 (3)
C3A—C11A1.394 (4)C3B—C11B1.389 (3)
C3A—N4A1.418 (3)C3B—N4B1.417 (3)
N4A—C5A1.392 (3)N4B—C5B1.388 (3)
N4A—C8A1.396 (3)N4B—C8B1.393 (3)
C5A—N6A1.315 (3)C5B—N6B1.321 (3)
C5A—C18A1.467 (4)C5B—C18B1.462 (4)
N6A—N7A1.369 (4)N6B—N7B1.374 (3)
N7A—C8A1.312 (4)N7B—C8B1.319 (3)
C8A—C9A1.413 (4)C8B—C9B1.413 (4)
C9A—C10A1.342 (4)C9B—C10B1.350 (4)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.429 (4)C10B—C11B1.433 (4)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.428 (4)C11B—C12B1.430 (3)
C12A—C13A1.343 (4)C12B—C13B1.359 (4)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.420 (4)C13B—C14B1.412 (4)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.400 (4)C14B—C15B1.404 (4)
C15A—C16A1.358 (4)C15B—C16B1.357 (4)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.403 (4)C16B—C17B1.406 (4)
C16A—H16A0.9500C16B—H16B0.9500
C17A—H17A0.9500C17B—H17B0.9500
C18A—C19A1.383 (4)C18B—C23B1.384 (3)
C18A—C23A1.397 (4)C18B—C19B1.392 (4)
C19A—C20A1.374 (4)C19B—C20B1.378 (4)
C19A—H19A0.9500C19B—H19B0.9500
C20A—C21A1.383 (4)C20B—C21B1.388 (4)
C20A—H20A0.9500C20B—H20B0.9500
C21A—O24A1.369 (3)C21B—O24B1.367 (3)
C21A—C22A1.389 (4)C21B—C22B1.387 (4)
C22A—C23A1.370 (4)C22B—C23B1.379 (4)
C22A—H22A0.9500C22B—H22B0.9500
C23A—H23A0.9500C23B—H23B0.9500
O24A—C25A1.426 (3)O24B—C25B1.430 (4)
C25A—C26A1.508 (4)C25B—C26B1.495 (5)
C25A—H25A0.9900C25B—H25C0.9900
C25A—H25B0.9900C25B—H25D0.9900
C26A—C27A1.512 (4)C26B—C27B1.523 (5)
C26A—H26A0.9900C26B—H26C0.9900
C26A—H26B0.9900C26B—H26D0.9900
C27A—C28A1.497 (4)C27B—C28B1.520 (5)
C27A—H27A0.9900C27B—H27C0.9900
C27A—H27B0.9900C27B—H27D0.9900
C28A—C29A1.537 (5)C28B—C29B1.517 (5)
C28A—H28A0.9900C28B—H28C0.9900
C28A—H28B0.9900C28B—H28D0.9900
C29A—C30A1.448 (5)C29B—C30B1.514 (5)
C29A—H29A0.9900C29B—H29C0.9900
C29A—H29B0.9900C29B—H29D0.9900
C30A—H30A0.9800C30B—H30D0.9800
C30A—H30B0.9800C30B—H30E0.9800
C30A—H30C0.9800C30B—H30F0.9800
C17A—N1A—C2A118.1 (2)C17B—N1B—C2B117.3 (2)
N1A—C2A—C14A121.6 (3)N1B—C2B—C14B122.8 (2)
N1A—C2A—C3A119.8 (2)N1B—C2B—C3B119.0 (2)
C14A—C2A—C3A118.6 (2)C14B—C2B—C3B118.1 (2)
C11A—C3A—N4A116.7 (2)C11B—C3B—N4B117.0 (2)
C11A—C3A—C2A120.1 (2)C11B—C3B—C2B120.2 (2)
N4A—C3A—C2A123.0 (2)N4B—C3B—C2B122.7 (2)
C5A—N4A—C8A103.8 (2)C5B—N4B—C8B104.2 (2)
C5A—N4A—C3A136.4 (2)C5B—N4B—C3B135.5 (2)
C8A—N4A—C3A119.6 (2)C8B—N4B—C3B120.3 (2)
N6A—C5A—N4A108.9 (3)N6B—C5B—N4B109.0 (2)
N6A—C5A—C18A119.3 (2)N6B—C5B—C18B121.0 (2)
N4A—C5A—C18A131.1 (2)N4B—C5B—C18B129.4 (2)
C5A—N6A—N7A109.7 (2)C5B—N6B—N7B109.3 (2)
C8A—N7A—N6A106.9 (2)C8B—N7B—N6B106.8 (2)
N7A—C8A—N4A110.6 (3)N7B—C8B—N4B110.5 (2)
N7A—C8A—C9A128.0 (3)N7B—C8B—C9B128.2 (2)
N4A—C8A—C9A121.3 (3)N4B—C8B—C9B120.9 (2)
C10A—C9A—C8A118.8 (3)C10B—C9B—C8B118.5 (2)
C10A—C9A—H9A120.6C10B—C9B—H9B120.7
C8A—C9A—H9A120.6C8B—C9B—H9B120.7
C9A—C10A—C11A120.6 (3)C9B—C10B—C11B121.0 (3)
C9A—C10A—H10A119.7C9B—C10B—H10B119.5
C11A—C10A—H10A119.7C11B—C10B—H10B119.5
C3A—C11A—C12A118.9 (3)C3B—C11B—C12B119.0 (2)
C3A—C11A—C10A121.6 (3)C3B—C11B—C10B120.9 (2)
C12A—C11A—C10A119.4 (3)C12B—C11B—C10B120.0 (2)
C13A—C12A—C11A121.9 (3)C13B—C12B—C11B121.1 (3)
C13A—C12A—H12A119.1C13B—C12B—H12B119.5
C11A—C12A—H12A119.1C11B—C12B—H12B119.5
C12A—C13A—C14A120.3 (2)C12B—C13B—C14B120.5 (2)
C12A—C13A—H13A119.9C12B—C13B—H13B119.8
C14A—C13A—H13A119.9C14B—C13B—H13B119.8
C15A—C14A—C13A122.3 (2)C15B—C14B—C13B122.8 (2)
C15A—C14A—C2A117.9 (3)C15B—C14B—C2B117.1 (2)
C13A—C14A—C2A119.8 (3)C13B—C14B—C2B120.0 (2)
C16A—C15A—C14A119.9 (3)C16B—C15B—C14B119.6 (2)
C16A—C15A—H15A120.1C16B—C15B—H15B120.2
C14A—C15A—H15A120.1C14B—C15B—H15B120.2
C15A—C16A—C17A118.2 (3)C15B—C16B—C17B119.0 (3)
C15A—C16A—H16A120.9C15B—C16B—H16B120.5
C17A—C16A—H16A120.9C17B—C16B—H16B120.5
N1A—C17A—C16A124.1 (3)N1B—C17B—C16B123.8 (3)
N1A—C17A—H17A117.9N1B—C17B—H17B118.1
C16A—C17A—H17A117.9C16B—C17B—H17B118.1
C19A—C18A—C23A118.0 (3)C23B—C18B—C19B118.8 (2)
C19A—C18A—C5A119.2 (2)C23B—C18B—C5B121.3 (2)
C23A—C18A—C5A122.4 (3)C19B—C18B—C5B119.7 (2)
C20A—C19A—C18A121.4 (3)C20B—C19B—C18B120.1 (3)
C20A—C19A—H19A119.3C20B—C19B—H19B119.9
C18A—C19A—H19A119.3C18B—C19B—H19B119.9
C19A—C20A—C21A120.2 (3)C19B—C20B—C21B120.4 (3)
C19A—C20A—H20A119.9C19B—C20B—H20B119.8
C21A—C20A—H20A119.9C21B—C20B—H20B119.8
O24A—C21A—C20A125.3 (3)O24B—C21B—C22B124.9 (3)
O24A—C21A—C22A115.7 (2)O24B—C21B—C20B115.2 (2)
C20A—C21A—C22A119.0 (3)C22B—C21B—C20B119.8 (3)
C23A—C22A—C21A120.5 (3)C23B—C22B—C21B119.3 (2)
C23A—C22A—H22A119.7C23B—C22B—H22B120.4
C21A—C22A—H22A119.7C21B—C22B—H22B120.4
C22A—C23A—C18A120.8 (3)C22B—C23B—C18B121.5 (2)
C22A—C23A—H23A119.6C22B—C23B—H23B119.3
C18A—C23A—H23A119.6C18B—C23B—H23B119.3
C21A—O24A—C25A118.0 (2)C21B—O24B—C25B119.1 (2)
O24A—C25A—C26A107.6 (2)O24B—C25B—C26B111.9 (3)
O24A—C25A—H25A110.2O24B—C25B—H25C109.2
C26A—C25A—H25A110.2C26B—C25B—H25C109.2
O24A—C25A—H25B110.2O24B—C25B—H25D109.2
C26A—C25A—H25B110.2C26B—C25B—H25D109.2
H25A—C25A—H25B108.5H25C—C25B—H25D107.9
C25A—C26A—C27A111.6 (3)C25B—C26B—C27B112.2 (3)
C25A—C26A—H26A109.3C25B—C26B—H26C109.2
C27A—C26A—H26A109.3C27B—C26B—H26C109.2
C25A—C26A—H26B109.3C25B—C26B—H26D109.2
C27A—C26A—H26B109.3C27B—C26B—H26D109.2
H26A—C26A—H26B108.0H26C—C26B—H26D107.9
C28A—C27A—C26A115.1 (3)C28B—C27B—C26B114.1 (3)
C28A—C27A—H27A108.5C28B—C27B—H27C108.7
C26A—C27A—H27A108.5C26B—C27B—H27C108.7
C28A—C27A—H27B108.5C28B—C27B—H27D108.7
C26A—C27A—H27B108.5C26B—C27B—H27D108.7
H27A—C27A—H27B107.5H27C—C27B—H27D107.6
C27A—C28A—C29A113.5 (3)C29B—C28B—C27B113.3 (3)
C27A—C28A—H28A108.9C29B—C28B—H28C108.9
C29A—C28A—H28A108.9C27B—C28B—H28C108.9
C27A—C28A—H28B108.9C29B—C28B—H28D108.9
C29A—C28A—H28B108.9C27B—C28B—H28D108.9
H28A—C28A—H28B107.7H28C—C28B—H28D107.7
C30A—C29A—C28A114.4 (4)C30B—C29B—C28B112.5 (3)
C30A—C29A—H29A108.7C30B—C29B—H29C109.1
C28A—C29A—H29A108.7C28B—C29B—H29C109.1
C30A—C29A—H29B108.7C30B—C29B—H29D109.1
C28A—C29A—H29B108.7C28B—C29B—H29D109.1
H29A—C29A—H29B107.6H29C—C29B—H29D107.8
C29A—C30A—H30A109.5C29B—C30B—H30D109.5
C29A—C30A—H30B109.5C29B—C30B—H30E109.5
H30A—C30A—H30B109.5H30D—C30B—H30E109.5
C29A—C30A—H30C109.5C29B—C30B—H30F109.5
H30A—C30A—H30C109.5H30D—C30B—H30F109.5
H30B—C30A—H30C109.5H30E—C30B—H30F109.5
C17A—N1A—C2A—C14A5.1 (4)C17B—N1B—C2B—C14B5.5 (4)
C17A—N1A—C2A—C3A178.1 (2)C17B—N1B—C2B—C3B178.4 (2)
N1A—C2A—C3A—C11A169.2 (2)N1B—C2B—C3B—C11B163.5 (2)
C14A—C2A—C3A—C11A7.7 (4)C14B—C2B—C3B—C11B12.8 (4)
N1A—C2A—C3A—N4A5.0 (4)N1B—C2B—C3B—N4B12.3 (4)
C14A—C2A—C3A—N4A178.1 (2)C14B—C2B—C3B—N4B171.5 (2)
C11A—C3A—N4A—C5A171.1 (3)C11B—C3B—N4B—C5B167.9 (3)
C2A—C3A—N4A—C5A14.5 (5)C2B—C3B—N4B—C5B16.2 (4)
C11A—C3A—N4A—C8A14.2 (4)C11B—C3B—N4B—C8B13.9 (3)
C2A—C3A—N4A—C8A160.2 (3)C2B—C3B—N4B—C8B162.0 (2)
C8A—N4A—C5A—N6A3.3 (3)C8B—N4B—C5B—N6B3.0 (3)
C3A—N4A—C5A—N6A171.9 (3)C3B—N4B—C5B—N6B175.4 (3)
C8A—N4A—C5A—C18A166.3 (3)C8B—N4B—C5B—C18B168.3 (3)
C3A—N4A—C5A—C18A18.4 (6)C3B—N4B—C5B—C18B13.3 (5)
N4A—C5A—N6A—N7A1.7 (4)N4B—C5B—N6B—N7B1.8 (3)
C18A—C5A—N6A—N7A169.4 (3)C18B—C5B—N6B—N7B170.3 (2)
C5A—N6A—N7A—C8A0.9 (4)C5B—N6B—N7B—C8B0.2 (3)
N6A—N7A—C8A—N4A3.1 (4)N6B—N7B—C8B—N4B2.2 (3)
N6A—N7A—C8A—C9A173.1 (3)N6B—N7B—C8B—C9B171.2 (3)
C5A—N4A—C8A—N7A3.9 (4)C5B—N4B—C8B—N7B3.2 (3)
C3A—N4A—C8A—N7A172.3 (3)C3B—N4B—C8B—N7B175.5 (2)
C5A—N4A—C8A—C9A172.5 (3)C5B—N4B—C8B—C9B170.7 (2)
C3A—N4A—C8A—C9A11.3 (4)C3B—N4B—C8B—C9B10.6 (4)
N7A—C8A—C9A—C10A176.7 (4)N7B—C8B—C9B—C10B173.7 (3)
N4A—C8A—C9A—C10A1.0 (5)N4B—C8B—C9B—C10B0.9 (4)
C8A—C9A—C10A—C11A5.7 (5)C8B—C9B—C10B—C11B4.9 (4)
N4A—C3A—C11A—C12A177.3 (2)N4B—C3B—C11B—C12B173.6 (2)
C2A—C3A—C11A—C12A8.1 (4)C2B—C3B—C11B—C12B10.4 (4)
N4A—C3A—C11A—C10A7.8 (4)N4B—C3B—C11B—C10B8.2 (4)
C2A—C3A—C11A—C10A166.8 (3)C2B—C3B—C11B—C10B167.8 (2)
C9A—C10A—C11A—C3A2.2 (5)C9B—C10B—C11B—C3B1.1 (4)
C9A—C10A—C11A—C12A172.6 (3)C9B—C10B—C11B—C12B177.1 (3)
C3A—C11A—C12A—C13A3.5 (4)C3B—C11B—C12B—C13B1.4 (4)
C10A—C11A—C12A—C13A171.5 (3)C10B—C11B—C12B—C13B176.8 (3)
C11A—C12A—C13A—C14A1.5 (4)C11B—C12B—C13B—C14B5.0 (4)
C12A—C13A—C14A—C15A177.5 (3)C12B—C13B—C14B—C15B173.9 (3)
C12A—C13A—C14A—C2A1.9 (4)C12B—C13B—C14B—C2B2.3 (4)
N1A—C2A—C14A—C15A5.2 (4)N1B—C2B—C14B—C15B6.8 (4)
C3A—C2A—C14A—C15A177.9 (2)C3B—C2B—C14B—C15B177.1 (2)
N1A—C2A—C14A—C13A174.2 (2)N1B—C2B—C14B—C13B169.7 (2)
C3A—C2A—C14A—C13A2.7 (4)C3B—C2B—C14B—C13B6.4 (4)
C13A—C14A—C15A—C16A177.7 (3)C13B—C14B—C15B—C16B173.8 (3)
C2A—C14A—C15A—C16A1.7 (4)C2B—C14B—C15B—C16B2.6 (4)
C14A—C15A—C16A—C17A1.7 (4)C14B—C15B—C16B—C17B2.3 (4)
C2A—N1A—C17A—C16A1.5 (4)C2B—N1B—C17B—C16B0.1 (4)
C15A—C16A—C17A—N1A1.9 (5)C15B—C16B—C17B—N1B3.8 (5)
N6A—C5A—C18A—C19A45.1 (4)N6B—C5B—C18B—C23B120.5 (3)
N4A—C5A—C18A—C19A146.1 (3)N4B—C5B—C18B—C23B49.9 (4)
N6A—C5A—C18A—C23A127.9 (3)N6B—C5B—C18B—C19B54.7 (4)
N4A—C5A—C18A—C23A40.8 (5)N4B—C5B—C18B—C19B135.0 (3)
C23A—C18A—C19A—C20A1.6 (4)C23B—C18B—C19B—C20B1.9 (4)
C5A—C18A—C19A—C20A175.0 (3)C5B—C18B—C19B—C20B177.1 (2)
C18A—C19A—C20A—C21A0.4 (5)C18B—C19B—C20B—C21B0.5 (4)
C19A—C20A—C21A—O24A179.0 (3)C19B—C20B—C21B—O24B177.5 (3)
C19A—C20A—C21A—C22A0.8 (5)C19B—C20B—C21B—C22B1.2 (4)
O24A—C21A—C22A—C23A179.1 (2)O24B—C21B—C22B—C23B177.0 (3)
C20A—C21A—C22A—C23A0.8 (4)C20B—C21B—C22B—C23B1.6 (4)
C21A—C22A—C23A—C18A0.5 (4)C21B—C22B—C23B—C18B0.2 (4)
C19A—C18A—C23A—C22A1.7 (4)C19B—C18B—C23B—C22B1.5 (4)
C5A—C18A—C23A—C22A174.8 (2)C5B—C18B—C23B—C22B176.6 (2)
C20A—C21A—O24A—C25A1.8 (4)C22B—C21B—O24B—C25B9.2 (4)
C22A—C21A—O24A—C25A178.3 (3)C20B—C21B—O24B—C25B172.1 (3)
C21A—O24A—C25A—C26A175.9 (2)C21B—O24B—C25B—C26B88.3 (3)
O24A—C25A—C26A—C27A179.0 (3)O24B—C25B—C26B—C27B178.3 (3)
C25A—C26A—C27A—C28A178.0 (3)C25B—C26B—C27B—C28B164.8 (3)
C26A—C27A—C28A—C29A178.9 (3)C26B—C27B—C28B—C29B177.5 (3)
C27A—C28A—C29A—C30A176.8 (4)C27B—C28B—C29B—C30B178.4 (3)

Experimental details

Crystal data
Chemical formulaC25H24N4O
Mr396.48
Crystal system, space groupMonoclinic, P21/c
Temperature (K)193
a, b, c (Å)9.746 (3), 36.787 (5), 12.174 (3)
β (°) 106.412 (12)
V3)4186.6 (17)
Z8
Radiation typeCu Kα
µ (mm1)0.62
Crystal size (mm)0.34 × 0.23 × 0.23
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8415, 7934, 5140
Rint0.051
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.170, 1.02
No. of reflections7934
No. of parameters543
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.30

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971), SIR97 (Altomare et al., 1999), SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009).

 

References

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Volume 71| Part 7| July 2015| Pages o521-o522
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