2-(4-Meth­oxy­phen­yl)-1-pentyl-4,5-di­phenyl-1H-imidazole

Simpson, J.; Mohamed, S.K.; Marzouk, A.A.; Talybov, A.H.; Abdelhamid, A.A.

doi:10.1107/S1600536812049100

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Pages o5-o6

https://doi.org/10.1107/S1600536812049100

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2-(4-Methoxyphenyl)-1-pentyl-4,5-diphenyl-1H-imidazole

Jim Simpson,^a Shaaban K. Mohamed,^b,^c ^* Adel A. Marzouk,^d Avtandil H. Talybov ^e and Antar A. Abdelhamid ^f

^aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand, ^bChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt, ^cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, ^eManedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan, and ^fChemistry Department, Faculty of Science, Sohag University, Sohag 82524, Egypt
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 27 November 2012; accepted 29 November 2012; online 5 December 2012)

The title compound, C₂₇H₂₈N₂O, is a lophine (2,4,5-triphenyl-1H-imidazole) derivative with an n-pentyl chain on the amine N atom and a 4-methoxy substituent on the benzene ring. The two phenyl and methoxybenzene rings are inclined to the imidazole ring at angles of 25.32 (7), 76.79 (5) and 35.42 (7)°, respectively, while the methoxy substituent lies close to the plane of its benzene ring, with a maximum deviation of 0.126 (3) Å for the methoxy C atom. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R₂²(22) loops. These dimers are stacked along the a-axis direction.

Related literature

For the non-linear optical and chemiluminescence properties of lophine and its derivatives, see: Santos et al. (2001 ); Radziszewski (1877 ); Maeda & Hayashi (1969 , 1970 ). For the bioactivity of imidazoles, see: Antolini et al. (1999 ); Eyers et al. (1998 ); Laszlo et al. (1999 ); Newman et al. (2000 ); Veisi et al. (2012 ); Wang et al. (2002 ). For related structures, see, for example: Yanover & Kaftory (2009a ,b ); Kison & Opatz (2009 ); Zhao et al. (2012 ). For representative bond lengths, see: Allen et al. (1987 ) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₇H₂₈N₂O
M_r = 396.51
Triclinic, $[P \overline 1]$
a = 9.7214 (19) Å
b = 10.739 (1) Å
c = 11.7367 (10) Å
α = 114.069 (4)°
β = 99.021 (6)°
γ = 95.425 (6)°
V = 1087.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 93 K
0.47 × 0.18 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2011 ) T_min = 0.619, T_max = 0.746
15574 measured reflections
4968 independent reflections
3542 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.132
S = 1.06
4968 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O119ⁱ	0.95	2.61	3.4393 (19)	146
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 and SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ) and TITAN2000 (Hunter & Simpson, 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812049100/bt6874sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049100/bt6874Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812049100/bt6874Isup3.cml

checkCIF report

Comment top

The chemilumescence properties of lophine, (2,4,5-triphenyl-1H-imidazole), and its derivatives have been known since the late 19t h century (Radziszewski, 1877) and their non-linear optical (Santos et al., 2001) and related optical properties (Maeda & Hayashi, 1969, 1970) have been extensively investigated. In addition, substituted imidazoles exhibit a wide range of biological activities for example as glucagon receptors (Laszlo et al., 1999), CB1 cannabinoid receptor antagonists (Eyers et al., 1998) and modulators of P-glycoprotein (P-gp)-mediated multi drug resistance (MDR) (Newman et al., 2000). They can also act as both antibacterial (Antolini et al., 1999) and antitumor agents (Wang et al., 2002) or as pesticides (Veisi et al., 2012). As part of our work on the synthesis of imidazole derivatives, we have prepared 2-(4-methoxyphenyl)-1-pentyl-4,5-diphenyl-1H-imidazole and report its preparation and structure here.

In the title compound, the lophine (2,4,5-triphenyl-1H-imidazole) skeleton (Yanover & Kaftory, 2009a) is embellished with a nicely ordered C22—C26 n-pentyl substituent on the amine N atom of the imidazole ring and a p-methoxy substituent on the C17—C21 benzene ring. The n-pentyl chain is almost orthogonal to the imidazole with a meanplane through C22···C26 (r.m.s. deviation = 0.047 /%A) that subtends a dihedral angle of 78.91 (7) ° to the plane of the imidazole ring. The two C4···C9 and C10···C15 phenyl rings are inclined to the imidazole ring at angles of 25.32 (7)°, 76.79 (5)° respectively while the methoxy substituted C17···C21 ring makes and angle of 35.42 (7)°. The methoxy substituent lies close to the plane of the C17···C21 benzene ring with a maximum deviation of only 0.126 (3) Å for the C119 atom. Bond distances in the structure are normal (Allen et al., 1987) and are comparable to those reported for related structures (Yanover & Kaftory, 2009a,b; Kison & Opatz, 2009; Zhao et al., 2012). In the crystal structure the only significant intermolecular contacts are C15—H15···O119 hydrogen bonds which form inversion dimers with R₂²(22) ring motifs (Bernstein et al., 1995). These dimers are further stacked along the a axis (Fig. 2), with alternating molecules arranged in a head to tail fashion (Fig. 3).

Related literature top

For the non-linear optical and chemiluminescence properties of lophine and its derivatives, see: Santos et al. (2001); Radziszewski (1877); Maeda & Hayashi (1969, 1970). For the bioactivity of imidazoles, see: Antolini et al. (1999); Eyers et al. (1998); Laszlo et al. (1999); Newman et al. (2000); Veisi et al. (2012); Wang et al. (2002). For related structures, see, for example: Yanover & Kaftory (2009a,b); Kison & Opatz (2009); Zhao et al. (2012). For representative bond lengths, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A 50-ml. volumetric flask equipped with a magnetic stirring bar was charged with 25 ml. of dimethyl sulfoxide and 2.4 g (40 mmol) potassium hydroxide. The mixture was stirred at room temperature for 5 minutes, then 3.26 g (10 mmol) 2-(4-methoxyphenyl)-4,5-diphenyl-1H-imidazole was added with stirring for a further 45 minutes. To this reaction mixture, 3.02 g. (20 mmol) pentyl bromide was added. After stirring for an additional 45 minutes the mixture was diluted with 20 ml water then extracted with diethyl ether (3x 20 ml). The combined ether layers were dried over calcium chloride and evaporated under slightly reduced pressure. The excess pentyl bromide was removed by distillation at approximately 15 mm, and the residue was crystallized from ethanol yielding 3.35 g (84%) of 2-(4-methoxyphenyl)-1-pentyl-4,5-diphenyl-1H-imidazole, m.p. 382–384 K.

Structure description top

For the non-linear optical and chemiluminescence properties of lophine and its derivatives, see: Santos et al. (2001); Radziszewski (1877); Maeda & Hayashi (1969, 1970). For the bioactivity of imidazoles, see: Antolini et al. (1999); Eyers et al. (1998); Laszlo et al. (1999); Newman et al. (2000); Veisi et al. (2012); Wang et al. (2002). For related structures, see, for example: Yanover & Kaftory (2009a,b); Kison & Opatz (2009); Zhao et al. (2012). For representative bond lengths, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 and SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The structure of I with ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal packing of I viewed along b showing centrosymmetric dimer formation. Hydrogen bonds are drawn as dashed lines.
	Fig. 3. Crystal packing of I showing stacks formed along a. Hydrogen bonds are drawn as dashed lines.

2-(4-Methoxyphenyl)-1-pentyl-4,5-diphenyl-1H-imidazole top

Crystal data top

C₂₇H₂₈N₂O	Z = 2
M_r = 396.51	F(000) = 424
Triclinic, P1	D_x = 1.211 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7214 (19) Å	Cell parameters from 3238 reflections
b = 10.739 (1) Å	θ = 2.6–26.1°
c = 11.7367 (10) Å	µ = 0.07 mm⁻¹
α = 114.069 (4)°	T = 93 K
β = 99.021 (6)°	Rectangular plate, colourless
γ = 95.425 (6)°	0.47 × 0.18 × 0.08 mm
V = 1087.7 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4968 independent reflections
Radiation source: fine-focus sealed tube	3542 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 27.6°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −12→12
T_min = 0.619, T_max = 0.746	k = −13→14
15574 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0663P)² + 0.0245P] where P = (F_o² + 2F_c²)/3
4968 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₇H₂₈N₂O	γ = 95.425 (6)°
M_r = 396.51	V = 1087.7 (3) Å³
Triclinic, P1	Z = 2
a = 9.7214 (19) Å	Mo Kα radiation
b = 10.739 (1) Å	µ = 0.07 mm⁻¹
c = 11.7367 (10) Å	T = 93 K
α = 114.069 (4)°	0.47 × 0.18 × 0.08 mm
β = 99.021 (6)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4968 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2011)	3542 reflections with I > 2σ(I)
T_min = 0.619, T_max = 0.746	R_int = 0.043
15574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.06	Δρ_max = 0.21 e Å⁻³
4968 reflections	Δρ_min = −0.25 e Å⁻³
273 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.65447 (14)	1.04609 (14)	0.93573 (12)	0.0209 (3)
C2	0.63626 (14)	0.90460 (14)	0.87092 (12)	0.0208 (3)
N2	0.73101 (12)	0.86376 (11)	0.94408 (10)	0.0214 (3)
C3	0.80178 (14)	0.98139 (14)	1.04912 (13)	0.0206 (3)
N1	0.75725 (12)	1.09265 (12)	1.04654 (10)	0.0218 (3)
C4	0.58701 (15)	1.14575 (14)	0.89992 (12)	0.0213 (3)
C5	0.65877 (16)	1.28159 (15)	0.94687 (13)	0.0252 (3)
H5	0.7490	1.3086	1.0031	0.030*
C6	0.60042 (16)	1.37763 (15)	0.91278 (14)	0.0276 (3)
H6	0.6507	1.4696	0.9454	0.033*
C7	0.46848 (16)	1.33933 (16)	0.83088 (14)	0.0290 (4)
H7	0.4288	1.4045	0.8064	0.035*
C8	0.39535 (17)	1.20596 (16)	0.78529 (14)	0.0283 (4)
H8	0.3045	1.1798	0.7302	0.034*
C9	0.45371 (15)	1.11015 (15)	0.81940 (13)	0.0244 (3)
H9	0.4022	1.0188	0.7875	0.029*
C10	0.54830 (15)	0.80462 (14)	0.74497 (13)	0.0210 (3)
C11	0.42624 (16)	0.71869 (15)	0.73438 (14)	0.0279 (4)
H11	0.3970	0.7226	0.8091	0.033*
C12	0.34667 (17)	0.62676 (16)	0.61431 (15)	0.0334 (4)
H12	0.2637	0.5677	0.6077	0.040*
C13	0.38700 (17)	0.62053 (16)	0.50497 (14)	0.0310 (4)
H13	0.3321	0.5577	0.4233	0.037*
C14	0.50733 (17)	0.70598 (16)	0.51489 (14)	0.0329 (4)
H14	0.5353	0.7026	0.4398	0.040*
C15	0.58783 (16)	0.79690 (15)	0.63386 (13)	0.0280 (4)
H15	0.6713	0.8548	0.6396	0.034*
C16	0.90797 (15)	0.98543 (14)	1.15551 (13)	0.0216 (3)
C17	1.00822 (15)	0.89913 (15)	1.14112 (13)	0.0240 (3)
H17	1.0102	0.8329	1.0579	0.029*
C18	1.10545 (15)	0.90705 (15)	1.24484 (13)	0.0249 (3)
H18	1.1723	0.8462	1.2326	0.030*
C19	1.10445 (15)	1.00433 (15)	1.36650 (13)	0.0243 (3)
O119	1.19783 (10)	1.02238 (11)	1.47489 (9)	0.0288 (3)
C119	1.28969 (17)	0.92355 (17)	1.46185 (15)	0.0351 (4)
H11A	1.2332	0.8303	1.4256	0.053*
H11B	1.3471	0.9442	1.5459	0.053*
H11C	1.3518	0.9283	1.4050	0.053*
C20	1.00777 (15)	1.09470 (15)	1.38280 (13)	0.0255 (3)
H20	1.0087	1.1633	1.4658	0.031*
C21	0.91080 (15)	1.08526 (15)	1.27931 (13)	0.0242 (3)
H21	0.8450	1.1471	1.2918	0.029*
C22	0.75400 (15)	0.72148 (14)	0.90983 (13)	0.0228 (3)
H22A	0.6625	0.6574	0.8669	0.027*
H22B	0.7908	0.7114	0.9886	0.027*
C23	0.85838 (15)	0.68150 (14)	0.82145 (13)	0.0241 (3)
H23A	0.8103	0.6648	0.7344	0.029*
H23B	0.9379	0.7599	0.8518	0.029*
C24	0.91712 (16)	0.55285 (15)	0.81503 (14)	0.0260 (3)
H24A	0.9624	0.5680	0.9024	0.031*
H24B	0.8381	0.4734	0.7814	0.031*
C25	1.02476 (16)	0.51780 (16)	0.73060 (14)	0.0311 (4)
H25A	0.9762	0.4906	0.6411	0.037*
H25B	1.0966	0.6017	0.7571	0.037*
C26	1.09912 (18)	0.40151 (16)	0.73654 (16)	0.0359 (4)
H26A	1.1529	0.4301	0.8237	0.054*
H26B	1.1637	0.3809	0.6775	0.054*
H26C	1.0286	0.3185	0.7122	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0207 (7)	0.0229 (7)	0.0170 (7)	0.0013 (6)	0.0033 (6)	0.0072 (6)
C2	0.0205 (7)	0.0251 (7)	0.0170 (7)	0.0031 (6)	0.0037 (5)	0.0097 (6)
N2	0.0241 (6)	0.0216 (6)	0.0168 (6)	0.0025 (5)	0.0030 (5)	0.0075 (5)
C3	0.0221 (7)	0.0216 (7)	0.0172 (7)	0.0025 (6)	0.0059 (6)	0.0071 (6)
N1	0.0229 (6)	0.0238 (6)	0.0180 (6)	0.0035 (5)	0.0047 (5)	0.0081 (5)
C4	0.0243 (7)	0.0244 (7)	0.0154 (7)	0.0067 (6)	0.0074 (6)	0.0070 (6)
C5	0.0268 (8)	0.0255 (8)	0.0196 (7)	0.0052 (6)	0.0032 (6)	0.0066 (6)
C6	0.0352 (9)	0.0212 (7)	0.0255 (8)	0.0044 (6)	0.0090 (7)	0.0083 (6)
C7	0.0373 (9)	0.0294 (8)	0.0235 (8)	0.0136 (7)	0.0083 (7)	0.0124 (7)
C8	0.0292 (8)	0.0331 (8)	0.0209 (7)	0.0088 (7)	0.0034 (6)	0.0098 (7)
C9	0.0259 (8)	0.0235 (8)	0.0211 (7)	0.0045 (6)	0.0054 (6)	0.0067 (6)
C10	0.0229 (7)	0.0201 (7)	0.0182 (7)	0.0053 (6)	0.0031 (6)	0.0067 (6)
C11	0.0296 (8)	0.0271 (8)	0.0222 (7)	0.0021 (6)	0.0084 (6)	0.0056 (6)
C12	0.0265 (8)	0.0299 (8)	0.0327 (9)	−0.0018 (7)	0.0048 (7)	0.0047 (7)
C13	0.0321 (9)	0.0293 (8)	0.0208 (7)	0.0055 (7)	−0.0042 (6)	0.0038 (6)
C14	0.0405 (9)	0.0363 (9)	0.0184 (7)	0.0037 (7)	0.0042 (7)	0.0096 (7)
C15	0.0292 (8)	0.0305 (8)	0.0223 (7)	−0.0008 (6)	0.0031 (6)	0.0116 (7)
C16	0.0223 (7)	0.0227 (7)	0.0187 (7)	0.0009 (6)	0.0033 (6)	0.0089 (6)
C17	0.0254 (8)	0.0257 (8)	0.0177 (7)	0.0023 (6)	0.0049 (6)	0.0065 (6)
C18	0.0225 (8)	0.0286 (8)	0.0238 (7)	0.0046 (6)	0.0053 (6)	0.0114 (6)
C19	0.0217 (7)	0.0316 (8)	0.0189 (7)	−0.0009 (6)	0.0008 (6)	0.0128 (6)
O119	0.0271 (6)	0.0383 (6)	0.0204 (5)	0.0066 (5)	0.0007 (4)	0.0135 (5)
C119	0.0310 (9)	0.0456 (10)	0.0290 (8)	0.0105 (8)	−0.0007 (7)	0.0180 (8)
C20	0.0277 (8)	0.0267 (8)	0.0185 (7)	0.0024 (6)	0.0055 (6)	0.0064 (6)
C21	0.0243 (8)	0.0255 (7)	0.0210 (7)	0.0040 (6)	0.0048 (6)	0.0084 (6)
C22	0.0249 (7)	0.0206 (7)	0.0214 (7)	0.0022 (6)	0.0013 (6)	0.0092 (6)
C23	0.0268 (8)	0.0234 (7)	0.0188 (7)	0.0033 (6)	0.0026 (6)	0.0068 (6)
C24	0.0276 (8)	0.0263 (8)	0.0227 (7)	0.0054 (6)	0.0037 (6)	0.0095 (6)
C25	0.0320 (9)	0.0300 (8)	0.0292 (8)	0.0073 (7)	0.0080 (7)	0.0097 (7)
C26	0.0339 (9)	0.0317 (9)	0.0369 (9)	0.0088 (7)	0.0076 (7)	0.0091 (7)

Geometric parameters (Å, º) top

C1—C2	1.3721 (19)	C16—C17	1.390 (2)
C1—N1	1.3811 (17)	C16—C21	1.4045 (19)
C1—C4	1.4716 (19)	C17—C18	1.3864 (19)
C2—N2	1.3833 (17)	C17—H17	0.9500
C2—C10	1.4848 (18)	C18—C19	1.386 (2)
N2—C3	1.3742 (17)	C18—H18	0.9500
N2—C22	1.4622 (17)	C19—O119	1.3724 (16)
C3—N1	1.3188 (17)	C19—C20	1.393 (2)
C3—C16	1.4730 (19)	O119—C119	1.4272 (18)
C4—C9	1.3950 (19)	C119—H11A	0.9800
C4—C5	1.396 (2)	C119—H11B	0.9800
C5—C6	1.386 (2)	C119—H11C	0.9800
C5—H5	0.9500	C20—C21	1.3772 (19)
C6—C7	1.389 (2)	C20—H20	0.9500
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.381 (2)	C22—C23	1.529 (2)
C7—H7	0.9500	C22—H22A	0.9900
C8—C9	1.384 (2)	C22—H22B	0.9900
C8—H8	0.9500	C23—C24	1.5225 (19)
C9—H9	0.9500	C23—H23A	0.9900
C10—C15	1.389 (2)	C23—H23B	0.9900
C10—C11	1.389 (2)	C24—C25	1.521 (2)
C11—C12	1.392 (2)	C24—H24A	0.9900
C11—H11	0.9500	C24—H24B	0.9900
C12—C13	1.378 (2)	C25—C26	1.521 (2)
C12—H12	0.9500	C25—H25A	0.9900
C13—C14	1.375 (2)	C25—H25B	0.9900
C13—H13	0.9500	C26—H26A	0.9800
C14—C15	1.384 (2)	C26—H26B	0.9800
C14—H14	0.9500	C26—H26C	0.9800
C15—H15	0.9500

C2—C1—N1	110.31 (12)	C18—C17—C16	121.84 (13)
C2—C1—C4	129.52 (12)	C18—C17—H17	119.1
N1—C1—C4	120.10 (12)	C16—C17—H17	119.1
C1—C2—N2	105.42 (11)	C19—C18—C17	119.52 (14)
C1—C2—C10	132.42 (13)	C19—C18—H18	120.2
N2—C2—C10	121.98 (12)	C17—C18—H18	120.2
C3—N2—C2	107.27 (11)	O119—C19—C18	124.04 (13)
C3—N2—C22	127.52 (12)	O119—C19—C20	116.28 (12)
C2—N2—C22	125.14 (11)	C18—C19—C20	119.63 (13)
N1—C3—N2	111.01 (12)	C19—O119—C119	117.07 (11)
N1—C3—C16	123.28 (12)	O119—C119—H11A	109.5
N2—C3—C16	125.62 (12)	O119—C119—H11B	109.5
C3—N1—C1	105.98 (11)	H11A—C119—H11B	109.5
C9—C4—C5	118.02 (13)	O119—C119—H11C	109.5
C9—C4—C1	122.72 (13)	H11A—C119—H11C	109.5
C5—C4—C1	119.25 (13)	H11B—C119—H11C	109.5
C6—C5—C4	121.02 (13)	C21—C20—C19	120.41 (13)
C6—C5—H5	119.5	C21—C20—H20	119.8
C4—C5—H5	119.5	C19—C20—H20	119.8
C5—C6—C7	119.98 (14)	C20—C21—C16	120.87 (14)
C5—C6—H6	120.0	C20—C21—H21	119.6
C7—C6—H6	120.0	C16—C21—H21	119.6
C8—C7—C6	119.63 (14)	N2—C22—C23	112.03 (12)
C8—C7—H7	120.2	N2—C22—H22A	109.2
C6—C7—H7	120.2	C23—C22—H22A	109.2
C7—C8—C9	120.34 (14)	N2—C22—H22B	109.2
C7—C8—H8	119.8	C23—C22—H22B	109.2
C9—C8—H8	119.8	H22A—C22—H22B	107.9
C8—C9—C4	121.00 (14)	C24—C23—C22	113.10 (12)
C8—C9—H9	119.5	C24—C23—H23A	109.0
C4—C9—H9	119.5	C22—C23—H23A	109.0
C15—C10—C11	118.59 (13)	C24—C23—H23B	109.0
C15—C10—C2	119.43 (13)	C22—C23—H23B	109.0
C11—C10—C2	121.97 (13)	H23A—C23—H23B	107.8
C10—C11—C12	120.06 (14)	C25—C24—C23	112.34 (12)
C10—C11—H11	120.0	C25—C24—H24A	109.1
C12—C11—H11	120.0	C23—C24—H24A	109.1
C13—C12—C11	120.69 (15)	C25—C24—H24B	109.1
C13—C12—H12	119.7	C23—C24—H24B	109.1
C11—C12—H12	119.7	H24A—C24—H24B	107.9
C14—C13—C12	119.50 (14)	C26—C25—C24	113.26 (14)
C14—C13—H13	120.2	C26—C25—H25A	108.9
C12—C13—H13	120.2	C24—C25—H25A	108.9
C13—C14—C15	120.24 (15)	C26—C25—H25B	108.9
C13—C14—H14	119.9	C24—C25—H25B	108.9
C15—C14—H14	119.9	H25A—C25—H25B	107.7
C14—C15—C10	120.91 (15)	C25—C26—H26A	109.5
C14—C15—H15	119.5	C25—C26—H26B	109.5
C10—C15—H15	119.5	H26A—C26—H26B	109.5
C17—C16—C21	117.68 (13)	C25—C26—H26C	109.5
C17—C16—C3	124.27 (12)	H26A—C26—H26C	109.5
C21—C16—C3	118.03 (13)	H26B—C26—H26C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O119ⁱ	0.95	2.61	3.4393 (19)	146

Symmetry code: (i) −x+2, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₈N₂O
M_r	396.51
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	9.7214 (19), 10.739 (1), 11.7367 (10)
α, β, γ (°)	114.069 (4), 99.021 (6), 95.425 (6)
V (Å³)	1087.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.47 × 0.18 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2011)
T_min, T_max	0.619, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	15574, 4968, 3542
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.132, 1.06
No. of reflections	4968
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

Computer programs: APEX2 (Bruker, 2011), APEX2 and SAINT (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999), SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O119ⁱ	0.95	2.61	3.4393 (19)	145.6

Symmetry code: (i) −x+2, −y+2, −z+2.

Acknowledgements

We thank the University of Otago for purchase of the diffractometer.

References

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