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

Qadri, T.; Anis, I.; Shah, M.R.; Ng, S.W.

doi:10.1107/S1600536811006374

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o738

doi:10.1107/S1600536811006374

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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 and Seik Weng Ng ^b ^*

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 7527, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 23 January 2011; accepted 19 February 2011; online 26 February 2011)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.051
wR(F²) = 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

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)
Symmetry code: (i) x-1, y, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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%).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₄₇H₅₄N₆O₂ at the 70% probability level with hydrogen atoms drawn as spheres of arbitrary radius.

2-(3-{[3-(1,2,3-benzotriazol-2-yl)-2-(prop-2-yn-1-yloxy)-5-(2,4,4- trimethylpentan-2-yl)phenyl]methyl}-2-(prop-2-yn-1-yloxy)-5-(2,4,4- trimethylpentan-2-yl)phenyl)-1,2,3-benzotriazole top

Crystal data top

C₄₇H₅₄N₆O₂	Z = 2
M_r = 734.96	F(000) = 788
Triclinic, P1	D_x = 1.160 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.4805 (4) Å	Cell parameters from 6715 reflections
b = 13.8247 (4) Å	θ = 2.5–29.3°
c = 14.6180 (6) Å	µ = 0.07 mm⁻¹
α = 104.808 (3)°	T = 100 K
β = 103.706 (3)°	Block, beige
γ = 100.642 (3)°	0.30 × 0.25 × 0.20 mm
V = 2103.58 (14) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	9290 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	6994 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −11→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −17→17
T_min = 0.822, T_max = 1.000	l = −18→18
17578 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0421P)² + 1.0461P] where P = (F_o² + 2F_c²)/3
9290 reflections	(Δ/σ)_max = 0.001
514 parameters	Δρ_max = 0.47 e Å⁻³
2 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₄₇H₅₄N₆O₂	γ = 100.642 (3)°
M_r = 734.96	V = 2103.58 (14) Å³
Triclinic, P1	Z = 2
a = 11.4805 (4) Å	Mo Kα radiation
b = 13.8247 (4) Å	µ = 0.07 mm⁻¹
c = 14.6180 (6) Å	T = 100 K
α = 104.808 (3)°	0.30 × 0.25 × 0.20 mm
β = 103.706 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	9290 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	6994 reflections with I > 2σ(I)
T_min = 0.822, T_max = 1.000	R_int = 0.031
17578 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	2 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.47 e Å⁻³
9290 reflections	Δρ_min = −0.30 e Å⁻³
514 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.62069 (10)	0.57849 (8)	0.68366 (8)	0.0181 (2)
O2	0.46427 (10)	0.92915 (9)	0.74295 (8)	0.0180 (2)
N1	0.75682 (14)	0.48200 (11)	0.55515 (11)	0.0253 (3)
N2	0.79630 (13)	0.58497 (10)	0.58114 (10)	0.0175 (3)
N3	0.91866 (13)	0.62735 (11)	0.61580 (10)	0.0210 (3)
N4	0.63903 (13)	1.12608 (10)	1.02490 (10)	0.0191 (3)
N5	0.62242 (12)	1.07152 (10)	0.93082 (9)	0.0170 (3)
N6	0.62881 (13)	1.12402 (11)	0.86637 (10)	0.0208 (3)
C1	0.86471 (17)	0.45397 (14)	0.57584 (13)	0.0243 (4)
C2	0.8856 (2)	0.35465 (16)	0.56490 (17)	0.0382 (5)
H2	0.8190	0.2935	0.5382	0.046*
C3	1.0059 (2)	0.35097 (17)	0.59449 (17)	0.0418 (6)
H3	1.0231	0.2854	0.5892	0.050*
C4	1.1068 (2)	0.44130 (18)	0.63295 (14)	0.0368 (5)
H4	1.1891	0.4345	0.6529	0.044*
C5	1.08845 (18)	0.53777 (16)	0.64196 (13)	0.0313 (4)
H5	1.1561	0.5981	0.6666	0.038*
C6	0.96427 (16)	0.54370 (14)	0.61302 (12)	0.0218 (4)
C7	0.71225 (15)	0.64916 (12)	0.57571 (11)	0.0164 (3)
C8	0.62335 (15)	0.64286 (12)	0.62555 (11)	0.0160 (3)
C9	0.54520 (14)	0.70952 (12)	0.62302 (11)	0.0159 (3)
C10	0.55881 (15)	0.77843 (12)	0.56992 (11)	0.0169 (3)
H10	0.5046	0.8226	0.5672	0.020*
C11	0.64859 (15)	0.78633 (12)	0.52001 (11)	0.0165 (3)
C12	0.72566 (15)	0.71951 (12)	0.52388 (11)	0.0175 (3)
H12	0.7876	0.7222	0.4909	0.021*
C13	0.52191 (16)	0.48396 (12)	0.63901 (12)	0.0214 (4)
H13A	0.5508	0.4290	0.5995	0.026*
H13B	0.4500	0.4956	0.5944	0.026*
C14	0.48590 (16)	0.45259 (13)	0.71871 (13)	0.0227 (4)
C15	0.45817 (19)	0.42907 (15)	0.78391 (15)	0.0319 (4)
C16	0.66093 (15)	0.86743 (13)	0.46638 (12)	0.0187 (3)
C17	0.53433 (16)	0.84807 (14)	0.38963 (12)	0.0229 (4)
H17A	0.5128	0.7787	0.3416	0.034*
H17B	0.5391	0.9001	0.3550	0.034*
H17C	0.4705	0.8531	0.4235	0.034*
C18	0.75675 (17)	0.85806 (14)	0.40902 (13)	0.0237 (4)
H18A	0.7281	0.7915	0.3558	0.036*
H18B	0.8367	0.8619	0.4543	0.036*
H18C	0.7665	0.9147	0.3803	0.036*
C19	0.68883 (15)	0.97889 (12)	0.53917 (12)	0.0193 (3)
H19A	0.6861	1.0258	0.4981	0.023*
H19B	0.6176	0.9802	0.5661	0.023*
C20	0.80758 (16)	1.03051 (13)	0.62902 (13)	0.0227 (4)
C21	0.8235 (2)	0.97002 (15)	0.70266 (14)	0.0368 (5)
H21A	0.8414	0.9048	0.6723	0.055*
H21B	0.7469	0.9552	0.7210	0.055*
H21C	0.8924	1.0112	0.7621	0.055*
C22	0.79155 (19)	1.13578 (14)	0.68323 (14)	0.0295 (4)
H22A	0.8666	1.1738	0.7387	0.044*
H22B	0.7200	1.1248	0.7084	0.044*
H22C	0.7779	1.1759	0.6371	0.044*
C23	0.92515 (19)	1.05220 (19)	0.59749 (16)	0.0462 (6)
H23A	0.9497	0.9877	0.5772	0.069*
H23B	0.9923	1.1028	0.6533	0.069*
H23C	0.9088	1.0800	0.5418	0.069*
C24	0.45816 (15)	0.71523 (12)	0.68700 (11)	0.0173 (3)
H24A	0.3871	0.7399	0.6573	0.021*
H24B	0.4254	0.6457	0.6914	0.021*
C25	0.53039 (14)	0.78978 (12)	0.78966 (11)	0.0163 (3)
C26	0.59913 (15)	0.75508 (12)	0.86006 (12)	0.0172 (3)
H26	0.5928	0.6829	0.8451	0.021*
C27	0.67730 (15)	0.82160 (12)	0.95195 (12)	0.0171 (3)
C28	0.68230 (15)	0.92638 (12)	0.97296 (12)	0.0171 (3)
H28	0.7345	0.9739	1.0348	0.020*
C29	0.61161 (15)	0.96223 (12)	0.90424 (12)	0.0165 (3)
C30	0.53422 (14)	0.89489 (12)	0.81258 (11)	0.0160 (3)
C31	0.75537 (15)	0.77823 (13)	1.02367 (12)	0.0191 (3)
C32	0.66482 (18)	0.70338 (15)	1.05332 (14)	0.0299 (4)
H32A	0.6130	0.7411	1.0849	0.045*
H32B	0.7122	0.6746	1.0999	0.045*
H32C	0.6118	0.6469	0.9940	0.045*
C33	0.83766 (17)	0.86281 (14)	1.11939 (13)	0.0266 (4)
H33A	0.7852	0.8932	1.1563	0.040*
H33B	0.8890	0.9169	1.1030	0.040*
H33C	0.8914	0.8325	1.1602	0.040*
C34	0.83234 (16)	0.71225 (13)	0.97307 (13)	0.0229 (4)
H34A	0.8710	0.6800	1.0214	0.027*
H34B	0.7716	0.6550	0.9169	0.027*
C35	0.93593 (17)	0.75639 (15)	0.93242 (13)	0.0274 (4)
C36	0.89336 (18)	0.81043 (16)	0.85695 (15)	0.0335 (5)
H36A	0.9604	0.8295	0.8289	0.050*
H36B	0.8719	0.8731	0.8896	0.050*
H36C	0.8203	0.7636	0.8038	0.050*
C37	0.9750 (2)	0.66217 (19)	0.87945 (17)	0.0488 (6)
H37A	1.0385	0.6850	0.8495	0.073*
H37B	0.9026	0.6127	0.8276	0.073*
H37C	1.0088	0.6288	0.9275	0.073*
C38	1.05044 (19)	0.8306 (2)	1.01414 (16)	0.0518 (7)
H38A	1.1175	0.8475	0.9854	0.078*
H38B	1.0775	0.7976	1.0644	0.078*
H38C	1.0297	0.8943	1.0449	0.078*
C39	0.36827 (15)	0.97167 (13)	0.77280 (12)	0.0194 (3)
H39A	0.3669	1.0357	0.7545	0.023*
H39B	0.3869	0.9901	0.8457	0.023*
C40	0.24673 (17)	0.89734 (14)	0.72536 (13)	0.0255 (4)
C41	0.14749 (19)	0.83803 (16)	0.68885 (17)	0.0388 (5)
C42	0.65798 (15)	1.22441 (13)	1.02168 (12)	0.0190 (3)
C43	0.68485 (16)	1.31885 (13)	1.09851 (13)	0.0252 (4)
H43	0.6879	1.3205	1.1644	0.030*
C44	0.70612 (17)	1.40743 (14)	1.07339 (14)	0.0297 (4)
H44	0.7256	1.4723	1.1235	0.036*
C45	0.70014 (18)	1.40630 (14)	0.97485 (15)	0.0314 (4)
H45	0.7158	1.4702	0.9612	0.038*
C46	0.67257 (18)	1.31596 (14)	0.89937 (14)	0.0287 (4)
H46	0.6677	1.3155	0.8335	0.034*
C47	0.65172 (15)	1.22327 (13)	0.92390 (12)	0.0206 (4)
H15	0.438 (2)	0.4082 (16)	0.8366 (12)	0.047 (6)*
H41	0.0684 (14)	0.7883 (15)	0.6599 (17)	0.060 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0199 (6)	0.0156 (5)	0.0173 (6)	0.0022 (5)	0.0042 (5)	0.0055 (4)
O2	0.0175 (6)	0.0234 (6)	0.0157 (5)	0.0079 (5)	0.0059 (4)	0.0077 (5)
N1	0.0278 (8)	0.0169 (7)	0.0367 (9)	0.0076 (6)	0.0168 (7)	0.0098 (6)
N2	0.0173 (7)	0.0162 (7)	0.0190 (7)	0.0043 (6)	0.0067 (5)	0.0045 (5)
N3	0.0170 (7)	0.0241 (7)	0.0194 (7)	0.0066 (6)	0.0041 (6)	0.0032 (6)
N4	0.0181 (7)	0.0212 (7)	0.0163 (7)	0.0043 (6)	0.0068 (6)	0.0020 (6)
N5	0.0179 (7)	0.0175 (7)	0.0151 (7)	0.0041 (6)	0.0052 (5)	0.0045 (5)
N6	0.0226 (8)	0.0192 (7)	0.0204 (7)	0.0046 (6)	0.0052 (6)	0.0076 (6)
C1	0.0298 (10)	0.0250 (9)	0.0294 (9)	0.0139 (8)	0.0182 (8)	0.0143 (8)
C2	0.0448 (13)	0.0301 (10)	0.0611 (14)	0.0200 (10)	0.0348 (11)	0.0254 (10)
C3	0.0586 (15)	0.0444 (13)	0.0558 (14)	0.0372 (12)	0.0393 (12)	0.0345 (11)
C4	0.0404 (12)	0.0596 (14)	0.0274 (10)	0.0361 (11)	0.0160 (9)	0.0205 (10)
C5	0.0271 (10)	0.0448 (12)	0.0214 (9)	0.0187 (9)	0.0047 (8)	0.0053 (8)
C6	0.0249 (9)	0.0289 (9)	0.0161 (8)	0.0137 (8)	0.0079 (7)	0.0082 (7)
C7	0.0148 (8)	0.0148 (7)	0.0169 (8)	0.0038 (6)	0.0029 (6)	0.0021 (6)
C8	0.0162 (8)	0.0162 (8)	0.0123 (7)	0.0017 (6)	0.0019 (6)	0.0032 (6)
C9	0.0125 (8)	0.0162 (8)	0.0143 (7)	0.0010 (6)	0.0017 (6)	0.0010 (6)
C10	0.0146 (8)	0.0178 (8)	0.0165 (8)	0.0045 (6)	0.0030 (6)	0.0034 (6)
C11	0.0156 (8)	0.0170 (8)	0.0144 (7)	0.0029 (6)	0.0027 (6)	0.0033 (6)
C12	0.0167 (8)	0.0186 (8)	0.0159 (8)	0.0037 (7)	0.0060 (6)	0.0029 (6)
C13	0.0230 (9)	0.0166 (8)	0.0213 (8)	0.0000 (7)	0.0069 (7)	0.0037 (7)
C14	0.0218 (9)	0.0188 (8)	0.0277 (9)	0.0055 (7)	0.0079 (7)	0.0069 (7)
C15	0.0341 (11)	0.0338 (11)	0.0361 (11)	0.0095 (9)	0.0170 (9)	0.0187 (9)
C16	0.0185 (8)	0.0212 (8)	0.0185 (8)	0.0066 (7)	0.0062 (6)	0.0081 (7)
C17	0.0230 (9)	0.0247 (9)	0.0211 (8)	0.0074 (7)	0.0043 (7)	0.0087 (7)
C18	0.0275 (10)	0.0266 (9)	0.0222 (9)	0.0096 (8)	0.0119 (7)	0.0106 (7)
C19	0.0201 (9)	0.0193 (8)	0.0217 (8)	0.0061 (7)	0.0082 (7)	0.0090 (7)
C20	0.0196 (9)	0.0252 (9)	0.0216 (9)	0.0035 (7)	0.0076 (7)	0.0047 (7)
C21	0.0439 (13)	0.0253 (10)	0.0276 (10)	0.0054 (9)	−0.0077 (9)	0.0050 (8)
C22	0.0342 (11)	0.0227 (9)	0.0264 (9)	0.0031 (8)	0.0053 (8)	0.0055 (8)
C23	0.0221 (11)	0.0617 (15)	0.0357 (11)	−0.0067 (10)	0.0102 (9)	−0.0058 (11)
C24	0.0142 (8)	0.0182 (8)	0.0183 (8)	0.0024 (6)	0.0051 (6)	0.0051 (6)
C25	0.0139 (8)	0.0190 (8)	0.0173 (8)	0.0033 (6)	0.0077 (6)	0.0056 (6)
C26	0.0167 (8)	0.0170 (8)	0.0193 (8)	0.0047 (7)	0.0079 (6)	0.0056 (6)
C27	0.0156 (8)	0.0212 (8)	0.0173 (8)	0.0054 (7)	0.0078 (6)	0.0077 (7)
C28	0.0158 (8)	0.0199 (8)	0.0153 (8)	0.0036 (7)	0.0062 (6)	0.0046 (6)
C29	0.0152 (8)	0.0160 (8)	0.0188 (8)	0.0036 (6)	0.0073 (6)	0.0045 (6)
C30	0.0136 (8)	0.0218 (8)	0.0158 (8)	0.0069 (7)	0.0065 (6)	0.0079 (6)
C31	0.0177 (8)	0.0218 (8)	0.0197 (8)	0.0066 (7)	0.0068 (7)	0.0078 (7)
C32	0.0269 (10)	0.0400 (11)	0.0321 (10)	0.0116 (9)	0.0109 (8)	0.0233 (9)
C33	0.0268 (10)	0.0315 (10)	0.0213 (9)	0.0142 (8)	0.0040 (7)	0.0061 (8)
C34	0.0238 (9)	0.0244 (9)	0.0207 (8)	0.0099 (7)	0.0044 (7)	0.0069 (7)
C35	0.0212 (9)	0.0398 (11)	0.0226 (9)	0.0124 (8)	0.0077 (7)	0.0077 (8)
C36	0.0260 (10)	0.0461 (12)	0.0358 (11)	0.0118 (9)	0.0164 (8)	0.0168 (9)
C37	0.0559 (15)	0.0667 (16)	0.0456 (13)	0.0417 (13)	0.0297 (12)	0.0225 (12)
C38	0.0215 (11)	0.0903 (19)	0.0316 (11)	0.0005 (12)	0.0081 (9)	0.0089 (12)
C39	0.0173 (8)	0.0222 (8)	0.0218 (8)	0.0093 (7)	0.0073 (7)	0.0075 (7)
C40	0.0214 (10)	0.0267 (9)	0.0279 (9)	0.0080 (8)	0.0074 (7)	0.0067 (8)
C41	0.0235 (11)	0.0349 (11)	0.0492 (13)	0.0047 (9)	0.0092 (9)	0.0021 (10)
C42	0.0139 (8)	0.0204 (8)	0.0214 (8)	0.0045 (7)	0.0055 (6)	0.0044 (7)
C43	0.0209 (9)	0.0248 (9)	0.0265 (9)	0.0055 (7)	0.0093 (7)	0.0005 (7)
C44	0.0264 (10)	0.0205 (9)	0.0355 (10)	0.0057 (8)	0.0079 (8)	−0.0010 (8)
C45	0.0337 (11)	0.0189 (9)	0.0400 (11)	0.0068 (8)	0.0069 (9)	0.0101 (8)
C46	0.0335 (11)	0.0245 (9)	0.0286 (10)	0.0076 (8)	0.0057 (8)	0.0123 (8)
C47	0.0174 (8)	0.0199 (8)	0.0232 (8)	0.0058 (7)	0.0036 (7)	0.0061 (7)

Geometric parameters (Å, º) top

O1—C8	1.3795 (19)	C22—H22A	0.9800
O1—C13	1.4442 (19)	C22—H22B	0.9800
O2—C30	1.3801 (19)	C22—H22C	0.9800
O2—C39	1.4446 (19)	C23—H23A	0.9800
N1—N2	1.3342 (19)	C23—H23B	0.9800
N1—C1	1.355 (2)	C23—H23C	0.9800
N2—N3	1.3343 (19)	C24—C25	1.519 (2)
N2—C7	1.429 (2)	C24—H24A	0.9900
N3—C6	1.350 (2)	C24—H24B	0.9900
N4—N5	1.3375 (18)	C25—C26	1.385 (2)
N4—C42	1.351 (2)	C25—C30	1.395 (2)
N5—N6	1.3350 (19)	C26—C27	1.396 (2)
N5—C29	1.434 (2)	C26—H26	0.9500
N6—C47	1.353 (2)	C27—C28	1.389 (2)
C1—C6	1.406 (3)	C27—C31	1.529 (2)
C1—C2	1.413 (3)	C28—C29	1.389 (2)
C2—C3	1.361 (3)	C28—H28	0.9500
C2—H2	0.9500	C29—C30	1.394 (2)
C3—C4	1.420 (3)	C31—C33	1.532 (2)
C3—H3	0.9500	C31—C32	1.544 (2)
C4—C5	1.367 (3)	C31—C34	1.556 (2)
C4—H4	0.9500	C32—H32A	0.9800
C5—C6	1.412 (2)	C32—H32B	0.9800
C5—H5	0.9500	C32—H32C	0.9800
C7—C12	1.386 (2)	C33—H33A	0.9800
C7—C8	1.390 (2)	C33—H33B	0.9800
C8—C9	1.401 (2)	C33—H33C	0.9800
C9—C10	1.384 (2)	C34—C35	1.547 (3)
C9—C24	1.521 (2)	C34—H34A	0.9900
C10—C11	1.401 (2)	C34—H34B	0.9900
C10—H10	0.9500	C35—C36	1.521 (3)
C11—C12	1.394 (2)	C35—C38	1.530 (3)
C11—C16	1.528 (2)	C35—C37	1.537 (3)
C12—H12	0.9500	C36—H36A	0.9800
C13—C14	1.462 (2)	C36—H36B	0.9800
C13—H13A	0.9900	C36—H36C	0.9800
C13—H13B	0.9900	C37—H37A	0.9800
C14—C15	1.175 (3)	C37—H37B	0.9800
C15—H15	0.951 (19)	C37—H37C	0.9800
C16—C18	1.538 (2)	C38—H38A	0.9800
C16—C17	1.540 (2)	C38—H38B	0.9800
C16—C19	1.558 (2)	C38—H38C	0.9800
C17—H17A	0.9800	C39—C40	1.460 (2)
C17—H17B	0.9800	C39—H39A	0.9900
C17—H17C	0.9800	C39—H39B	0.9900
C18—H18A	0.9800	C40—C41	1.183 (3)
C18—H18B	0.9800	C41—H41	0.956 (10)
C18—H18C	0.9800	C42—C47	1.410 (2)
C19—C20	1.551 (2)	C42—C43	1.414 (2)
C19—H19A	0.9900	C43—C44	1.362 (3)
C19—H19B	0.9900	C43—H43	0.9500
C20—C21	1.521 (3)	C44—C45	1.422 (3)
C20—C23	1.530 (3)	C44—H44	0.9500
C20—C22	1.536 (2)	C45—C46	1.364 (3)
C21—H21A	0.9800	C45—H45	0.9500
C21—H21B	0.9800	C46—C47	1.411 (2)
C21—H21C	0.9800	C46—H46	0.9500

C8—O1—C13	113.93 (12)	C20—C23—H23C	109.5
C30—O2—C39	114.29 (12)	H23A—C23—H23C	109.5
N2—N1—C1	102.29 (14)	H23B—C23—H23C	109.5
N3—N2—N1	117.53 (14)	C25—C24—C9	108.40 (13)
N3—N2—C7	120.33 (13)	C25—C24—H24A	110.0
N1—N2—C7	122.11 (13)	C9—C24—H24A	110.0
N2—N3—C6	102.41 (13)	C25—C24—H24B	110.0
N5—N4—C42	102.34 (13)	C9—C24—H24B	110.0
N6—N5—N4	117.52 (13)	H24A—C24—H24B	108.4
N6—N5—C29	122.02 (12)	C26—C25—C30	119.10 (14)
N4—N5—C29	120.13 (13)	C26—C25—C24	120.18 (14)
N5—N6—C47	102.38 (13)	C30—C25—C24	120.62 (15)
N1—C1—C6	108.80 (15)	C25—C26—C27	122.80 (15)
N1—C1—C2	130.06 (18)	C25—C26—H26	118.6
C6—C1—C2	121.14 (18)	C27—C26—H26	118.6
C3—C2—C1	116.6 (2)	C28—C27—C26	117.44 (15)
C3—C2—H2	121.7	C28—C27—C31	122.76 (14)
C1—C2—H2	121.7	C26—C27—C31	119.78 (14)
C2—C3—C4	122.51 (19)	C29—C28—C27	120.53 (15)
C2—C3—H3	118.7	C29—C28—H28	119.7
C4—C3—H3	118.7	C27—C28—H28	119.7
C5—C4—C3	121.61 (19)	C28—C29—C30	121.39 (15)
C5—C4—H4	119.2	C28—C29—N5	117.37 (14)
C3—C4—H4	119.2	C30—C29—N5	121.24 (15)
C4—C5—C6	116.91 (19)	O2—C30—C29	122.25 (14)
C4—C5—H5	121.5	O2—C30—C25	119.07 (14)
C6—C5—H5	121.5	C29—C30—C25	118.66 (15)
N3—C6—C1	108.96 (15)	C27—C31—C33	112.41 (14)
N3—C6—C5	129.86 (17)	C27—C31—C32	107.48 (14)
C1—C6—C5	121.17 (17)	C33—C31—C32	107.02 (14)
C12—C7—C8	121.83 (15)	C27—C31—C34	111.73 (13)
C12—C7—N2	118.48 (14)	C33—C31—C34	111.62 (14)
C8—C7—N2	119.63 (14)	C32—C31—C34	106.16 (14)
O1—C8—C7	119.86 (14)	C31—C32—H32A	109.5
O1—C8—C9	120.97 (14)	C31—C32—H32B	109.5
C7—C8—C9	118.90 (15)	H32A—C32—H32B	109.5
C10—C9—C8	118.53 (14)	C31—C32—H32C	109.5
C10—C9—C24	120.36 (14)	H32A—C32—H32C	109.5
C8—C9—C24	120.71 (14)	H32B—C32—H32C	109.5
C9—C10—C11	123.25 (15)	C31—C33—H33A	109.5
C9—C10—H10	118.4	C31—C33—H33B	109.5
C11—C10—H10	118.4	H33A—C33—H33B	109.5
C12—C11—C10	117.22 (15)	C31—C33—H33C	109.5
C12—C11—C16	122.74 (14)	H33A—C33—H33C	109.5
C10—C11—C16	120.02 (14)	H33B—C33—H33C	109.5
C7—C12—C11	120.26 (15)	C35—C34—C31	123.94 (15)
C7—C12—H12	119.9	C35—C34—H34A	106.3
C11—C12—H12	119.9	C31—C34—H34A	106.3
O1—C13—C14	107.94 (13)	C35—C34—H34B	106.3
O1—C13—H13A	110.1	C31—C34—H34B	106.3
C14—C13—H13A	110.1	H34A—C34—H34B	106.4
O1—C13—H13B	110.1	C36—C35—C38	108.52 (18)
C14—C13—H13B	110.1	C36—C35—C37	107.67 (16)
H13A—C13—H13B	108.4	C38—C35—C37	107.99 (18)
C15—C14—C13	178.8 (2)	C36—C35—C34	113.78 (15)
C14—C15—H15	177.3 (14)	C38—C35—C34	113.00 (15)
C11—C16—C18	112.27 (14)	C37—C35—C34	105.57 (17)
C11—C16—C17	107.74 (13)	C35—C36—H36A	109.5
C18—C16—C17	107.06 (14)	C35—C36—H36B	109.5
C11—C16—C19	111.17 (13)	H36A—C36—H36B	109.5
C18—C16—C19	111.89 (13)	C35—C36—H36C	109.5
C17—C16—C19	106.36 (13)	H36A—C36—H36C	109.5
C16—C17—H17A	109.5	H36B—C36—H36C	109.5
C16—C17—H17B	109.5	C35—C37—H37A	109.5
H17A—C17—H17B	109.5	C35—C37—H37B	109.5
C16—C17—H17C	109.5	H37A—C37—H37B	109.5
H17A—C17—H17C	109.5	C35—C37—H37C	109.5
H17B—C17—H17C	109.5	H37A—C37—H37C	109.5
C16—C18—H18A	109.5	H37B—C37—H37C	109.5
C16—C18—H18B	109.5	C35—C38—H38A	109.5
H18A—C18—H18B	109.5	C35—C38—H38B	109.5
C16—C18—H18C	109.5	H38A—C38—H38B	109.5
H18A—C18—H18C	109.5	C35—C38—H38C	109.5
H18B—C18—H18C	109.5	H38A—C38—H38C	109.5
C20—C19—C16	123.93 (14)	H38B—C38—H38C	109.5
C20—C19—H19A	106.3	O2—C39—C40	110.99 (13)
C16—C19—H19A	106.3	O2—C39—H39A	109.4
C20—C19—H19B	106.3	C40—C39—H39A	109.4
C16—C19—H19B	106.3	O2—C39—H39B	109.4
H19A—C19—H19B	106.4	C40—C39—H39B	109.4
C21—C20—C23	110.31 (18)	H39A—C39—H39B	108.0
C21—C20—C22	107.26 (15)	C41—C40—C39	178.5 (2)
C23—C20—C22	107.14 (16)	C40—C41—H41	178.0 (16)
C21—C20—C19	113.27 (15)	N4—C42—C47	108.93 (14)
C23—C20—C19	112.49 (15)	N4—C42—C43	130.09 (16)
C22—C20—C19	105.95 (15)	C47—C42—C43	120.94 (16)
C20—C21—H21A	109.5	C44—C43—C42	116.72 (17)
C20—C21—H21B	109.5	C44—C43—H43	121.6
H21A—C21—H21B	109.5	C42—C43—H43	121.6
C20—C21—H21C	109.5	C43—C44—C45	122.34 (16)
H21A—C21—H21C	109.5	C43—C44—H44	118.8
H21B—C21—H21C	109.5	C45—C44—H44	118.8
C20—C22—H22A	109.5	C46—C45—C44	121.85 (18)
C20—C22—H22B	109.5	C46—C45—H45	119.1
H22A—C22—H22B	109.5	C44—C45—H45	119.1
C20—C22—H22C	109.5	C45—C46—C47	116.80 (18)
H22A—C22—H22C	109.5	C45—C46—H46	121.6
H22B—C22—H22C	109.5	C47—C46—H46	121.6
C20—C23—H23A	109.5	N6—C47—C42	108.82 (15)
C20—C23—H23B	109.5	N6—C47—C46	129.79 (16)
H23A—C23—H23B	109.5	C42—C47—C46	121.34 (15)

C1—N1—N2—N3	0.61 (18)	C16—C19—C20—C23	67.1 (2)
C1—N1—N2—C7	−177.38 (14)	C16—C19—C20—C22	−176.18 (15)
N1—N2—N3—C6	−0.50 (18)	C10—C9—C24—C25	−88.59 (17)
C7—N2—N3—C6	177.52 (14)	C8—C9—C24—C25	84.04 (17)
C42—N4—N5—N6	0.14 (18)	C9—C24—C25—C26	−85.49 (18)
C42—N4—N5—C29	173.68 (14)	C9—C24—C25—C30	90.85 (17)
N4—N5—N6—C47	−0.13 (18)	C30—C25—C26—C27	−3.1 (2)
C29—N5—N6—C47	−173.53 (14)	C24—C25—C26—C27	173.28 (14)
N2—N1—C1—C6	−0.44 (18)	C25—C26—C27—C28	1.7 (2)
N2—N1—C1—C2	179.75 (19)	C25—C26—C27—C31	−176.83 (14)
N1—C1—C2—C3	−178.54 (19)	C26—C27—C28—C29	0.0 (2)
C6—C1—C2—C3	1.7 (3)	C31—C27—C28—C29	178.46 (14)
C1—C2—C3—C4	−1.1 (3)	C27—C28—C29—C30	−0.2 (2)
C2—C3—C4—C5	−0.4 (3)	C27—C28—C29—N5	−179.48 (14)
C3—C4—C5—C6	1.2 (3)	N6—N5—C29—C28	138.04 (15)
N2—N3—C6—C1	0.17 (17)	N4—N5—C29—C28	−35.2 (2)
N2—N3—C6—C5	−178.86 (17)	N6—N5—C29—C30	−41.3 (2)
N1—C1—C6—N3	0.2 (2)	N4—N5—C29—C30	145.51 (15)
C2—C1—C6—N3	−179.99 (16)	C39—O2—C30—C29	−65.62 (19)
N1—C1—C6—C5	179.31 (15)	C39—O2—C30—C25	116.27 (15)
C2—C1—C6—C5	−0.9 (3)	C28—C29—C30—O2	−179.32 (14)
C4—C5—C6—N3	178.34 (17)	N5—C29—C30—O2	0.0 (2)
C4—C5—C6—C1	−0.6 (3)	C28—C29—C30—C25	−1.2 (2)
N3—N2—C7—C12	55.3 (2)	N5—C29—C30—C25	178.07 (14)
N1—N2—C7—C12	−126.81 (16)	C26—C25—C30—O2	−179.05 (13)
N3—N2—C7—C8	−122.00 (16)	C24—C25—C30—O2	4.6 (2)
N1—N2—C7—C8	55.9 (2)	C26—C25—C30—C29	2.8 (2)
C13—O1—C8—C7	−104.28 (16)	C24—C25—C30—C29	−173.61 (14)
C13—O1—C8—C9	81.71 (17)	C28—C27—C31—C33	0.1 (2)
C12—C7—C8—O1	−174.05 (13)	C26—C27—C31—C33	178.55 (15)
N2—C7—C8—O1	3.1 (2)	C28—C27—C31—C32	117.60 (17)
C12—C7—C8—C9	0.1 (2)	C26—C27—C31—C32	−63.94 (19)
N2—C7—C8—C9	177.24 (13)	C28—C27—C31—C34	−126.31 (16)
O1—C8—C9—C10	174.77 (13)	C26—C27—C31—C34	52.1 (2)
C7—C8—C9—C10	0.7 (2)	C27—C31—C34—C35	63.8 (2)
O1—C8—C9—C24	2.0 (2)	C33—C31—C34—C35	−63.1 (2)
C7—C8—C9—C24	−172.06 (14)	C32—C31—C34—C35	−179.34 (16)
C8—C9—C10—C11	−1.3 (2)	C31—C34—C35—C36	−56.0 (2)
C24—C9—C10—C11	171.51 (14)	C31—C34—C35—C38	68.3 (2)
C9—C10—C11—C12	1.0 (2)	C31—C34—C35—C37	−173.84 (17)
C9—C10—C11—C16	−177.59 (14)	C30—O2—C39—C40	−102.14 (16)
C8—C7—C12—C11	−0.4 (2)	N5—N4—C42—C47	−0.09 (17)
N2—C7—C12—C11	−177.54 (14)	N5—N4—C42—C43	−177.86 (17)
C10—C11—C12—C7	−0.2 (2)	N4—C42—C43—C44	176.48 (17)
C16—C11—C12—C7	178.39 (14)	C47—C42—C43—C44	−1.1 (2)
C8—O1—C13—C14	−149.87 (14)	C42—C43—C44—C45	0.9 (3)
C12—C11—C16—C18	6.2 (2)	C43—C44—C45—C46	0.0 (3)
C10—C11—C16—C18	−175.24 (14)	C44—C45—C46—C47	−0.8 (3)
C12—C11—C16—C17	123.87 (16)	N5—N6—C47—C42	0.06 (17)
C10—C11—C16—C17	−57.60 (18)	N5—N6—C47—C46	177.52 (18)
C12—C11—C16—C19	−119.96 (16)	N4—C42—C47—N6	0.02 (19)
C10—C11—C16—C19	58.56 (19)	C43—C42—C47—N6	178.03 (15)
C11—C16—C19—C20	62.8 (2)	N4—C42—C47—C46	−177.70 (16)
C18—C16—C19—C20	−63.7 (2)	C43—C42—C47—C46	0.3 (3)
C17—C16—C19—C20	179.77 (15)	C45—C46—C47—N6	−176.57 (18)
C16—C19—C20—C21	−58.9 (2)	C45—C46—C47—C42	0.6 (3)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₄₇H₅₄N₆O₂
M_r	734.96
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	11.4805 (4), 13.8247 (4), 14.6180 (6)
α, β, γ (°)	104.808 (3), 103.706 (3), 100.642 (3)
V (Å³)	2103.58 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.822, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17578, 9290, 6994
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.127, 1.01
No. of reflections	9290
No. of parameters	514
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.30

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (i) x−1, y, z.

Acknowledgements

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

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Ali, Q., Anis, I., Raza Shah, M. & Ng, S. W. (2011). Acta Cryst. E67, o533. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 3| March 2011| Page o738

doi:10.1107/S1600536811006374

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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