Bis[3-(2H-benzotriazol-2-yl)-2-(prop-2-yn­yloxy)-5-(2,4,4-trimethyl­pentan-2-yl)phen­yl]methane

Tahir Qadri; Itrat Anis; M R Shah; Seik Weng Ng

doi:10.1107/S1600536811006374

. 2011 Feb 26;67(Pt 3):o738. doi: 10.1107/S1600536811006374

Bis[3-(2H-benzotriazol-2-yl)-2-(prop-2-ynyloxy)-5-(2,4,4-trimethylpentan-2-yl)phenyl]methane

Tahir Qadri ^a, Itrat Anis ^a, M R Shah ^a, Seik Weng Ng ^b,^*

PMCID: PMC3051933 PMID: 21522477

Abstract

In the title compound, C₄₇H₅₄N₆O₂, the C—C—C bond angle between the rings is 108.40 (13)°. One aryl ring aligned at 38.5 (1)° with respect to the N-heterocyclic substituent and the other at 56.0 (1)° with respect to its substituent. In the crystal, adjacent molecules are linked by C—H⋯N hydrogen bonds, forming a chain extending along the a axis.

Related literature

For a similar compound, see: Ali et al. (2011 ▶).

Experimental

Crystal data

C₄₇H₅₄N₆O₂
M _r = 734.96
Triclinic,
a = 11.4805 (4) Å
b = 13.8247 (4) Å
c = 14.6180 (6) Å
α = 104.808 (3)°
β = 103.706 (3)°
γ = 100.642 (3)°
V = 2103.58 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.822, T _max = 1.000
17578 measured reflections
9290 independent reflections
6994 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.127
S = 1.01
9290 reflections
514 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006374/zs2092sup1.cif

e-67-0o738-sup1.cif^{(33.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006374/zs2092Isup2.hkl

e-67-0o738-Isup2.hkl^{(454.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C41—H41⋯N3ⁱ	0.96 (1)	2.38 (1)	3.283 (3)	158 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Some background on di(aryl)methane compounds having oxyacetate substituents was presented in an earlier report (Ali et al., 2011). The title compound also has an N-heterocyclic substituent in the rings (Scheme I).

Experimental

6,6'-Methylenebis(2-(2H-benzo[d][1,2,3]triazol-2-yl)-4-(2,4,4-\ trimethylpentan-2-yl)phenol) (0.01 g) and potassium carbonate (0.05 g) were dissolved in acetone (20 ml) at 323 K. Propargyl bromide (0.04 ml) was added and the reaction was stirred for 20 h. The progress of the reaction was monitored by thin layer chromatography (hexane: dichloromethane 60:40). The reaction was quenched by adding 1 M hydrochloric acid (10 ml). The aqueous phase was extracted with dichloromethane, the solvent evaporated and the crude product was recrystallized from dichloromethane (yield 80%).