1-{2-Benz­yloxy-2-[4-(morpholin-4-yl)phen­yl]eth­yl}-1H-benzimidazole

Özel Güven, Ö.; Çapanlar, S.; Adler, P.D.F.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536812051306

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 1| January 2013| Pages o147-o148

https://doi.org/10.1107/S1600536812051306

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1-{2-Benzyloxy-2-[4-(morpholin-4-yl)phenyl]ethyl}-1H-benzimidazole

Özden Özel Güven,^a Seval Çapanlar,^a Philip D. F. Adler,^b Simon J. Coles ^b and Tuncer Hökelek ^c ^*

^aDepartment of Chemistry, Bülent Ecevit University, 67100 Zonguldak, Turkey, ^bDepartment of Chemistry, Southampton University, SO17 1BJ Southampton, England, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 30 November 2012; accepted 19 December 2012; online 22 December 2012)

In the title compound, C₂₆H₂₇N₃O₂, the morpholine ring adopts a chair conformation. The benzene and phenyl rings are inclined to the benzimidazole mean plane by 7.28 (6) and 61.45 (4)°, respectively. In the crystal, pairs of weak C—H⋯O hydrogen bonds link the molecules into inversion dimers. These dimers are further connected via weak C—H⋯N hydrogen bonds. A weak C—H⋯π interaction is also observed.

Related literature

For general background to the biological activity of benzimidazole derivatives, see: Özel Güven et al. (2007a ,b ). For related structures, see: Caira et al. (2004 ); Freer et al. (1986 ); Özel Güven et al. (2008a ,b ,c ); Peeters et al. (1979a ,b , 1996 ). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₆H₂₇N₃O₂
M_r = 413.51
Triclinic, $[P \overline 1]$
a = 9.4719 (3) Å
b = 10.5057 (3) Å
c = 11.8110 (4) Å
α = 96.824 (3)°
β = 108.953 (4)°
γ = 98.312 (3)°
V = 1082.51 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.32 × 0.25 × 0.22 mm

Data collection

Rigaku Saturn724+ diffractometer
13756 measured reflections
4972 independent reflections
3736 reflections with I > 2σ(I)
R_int = 0.043
3 standard reflections every 2 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.135
S = 1.06
4972 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2ⁱ	0.93	2.58	3.478 (2)	163
C6—H6⋯N3ⁱⁱ	0.93	2.56	3.439 (2)	159
C2—H2A⋯Cgⁱⁱⁱ	0.97	2.66	3.451 (2)	139
Symmetry codes: (i) -x, -y, -z; (ii) x, y, z+1; (iii) -x, -y+1, -z+1.

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812051306/cv5371sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812051306/cv5371Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812051306/cv5371Isup3.cml

checkCIF report

Comment top

The azole compounds possessing an imidazole or triazole ring (such as econazole, miconazole, ketoconazole, fluconazole and itraconazole) have been known as antifungal agents and used in clinics. Similar structures possessing benzimidazole ring in place of imidazole ring of miconazole and econazole have been reported to show antibacterial activity higher than antifungal activity (Özel Güven et al., 2007a,b). The crystal structures of econazole (Freer et al., 1986), miconazole (Peeters et al., 1979a), ketoconazole (Peeters et al., 1979b), fluconazole (Caira et al., 2004) and itraconazole (Peeters et al., 1996) have been reported, previously. Crystal structures of similar ether compounds having benzimidazole ring have been reported (Özel Güven et al., 2008a,b,c). Herewith we report the crystal structure of the title compound (I), which is a new benzimidazole derivative.

In (I) (Fig. 1), the bond lengths and angles are within normal ranges. The benzimidazole [A (N1/N2/C3–C9)] ring system is approximately planar with a maximum deviation of -0.010 (2) Å for atom C2 and its mean plane is oriented with respect to the benzene [B (C11–C16)] and phenyl [C (C17–C22)] rings at dihedral angles of A/B = 7.28 (6) and A/C = 61.45 (4) °. The dihedral angle between benzene and phenyl rings is B/C = 54.96 (5)°. Atom C10 is -0.008 (2) Å away from the plane of the benzene ring and atoms C1 and N3 are 0.056 (2) and 0.076 (2) Å away from the plane of the phenyl ring. The morpholine ring D (C23–C26/O2/N3) is not planar, but adopting a chair conformation with puckering parameters (Cremer & Pople, 1975) Q_T = 1.060 (5)Å, φ = 34.3 (2)° and θ = 57.3 (1)°.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric R₂²(28) dimers (Bernstein et al., 1995). These dimers are further connected via weak intermolecular C—H···N hydrogen bonds (Table 1), linking the molecules into centrosymmetric R₄⁴(16) dimers, to form a 2-D network (Fig. 2). A weak C—H···π interaction (Table 1) is also observed.

Related literature top

For general background to the biological activity of benzimidazole derivatives, see: Özel Güven et al. (2007a,b). For related structures, see: Caira et al. (2004); Freer et al. (1986); Özel Güven et al. (2008a,b,c); Peeters et al. (1979a,b, 1996). For hydrogen-bonding motifs, see: Bernstein et al. (1995). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound, (I), was synthesized by the reaction of 2-(1H-benzimidazol-1-yl)-1-(4-morpholinophenyl)ethanol with aryl halide using sodium hydrate. NaH (0.025 g, 0.618 mmol) was added to a solution of alcohol (0.2 g, 0.618 mmol) in DMF (4 ml) in small fractions. After stirring the mixture a few minutes, benzyl bromide (0.073 ml, 0.618 mmol) was added dropwise. Then, the reaction mixture was stirred additional 3 h at room temperature. The reaction was stopped by adding a small amount of methyl alcohol. After evaporation of the solvent, dichloromethane was added to the reaction mixture and extracted with water. The organic phase was separated and dried with anhydrous magnesium sulfate, then evaporated to dryness. The residue was purified by column chromatography using chloroform and crystallized from DMSO:H₂O (1:1) to obtain colorless crystals suitable for X-ray analysis (yield; 0.089 g, 35%).

Structure description top

For general background to the biological activity of benzimidazole derivatives, see: Özel Güven et al. (2007a,b). For related structures, see: Caira et al. (2004); Freer et al. (1986); Özel Güven et al. (2008a,b,c); Peeters et al. (1979a,b, 1996). For hydrogen-bonding motifs, see: Bernstein et al. (1995). For ring puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram. C–H···O and C–H···N hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

1-{2-Benzyloxy-2-[4-(morpholin-4-yl)phenyl]ethyl}-1H-benzimidazole top

Crystal data top

C₂₆H₂₇N₃O₂	Z = 2
M_r = 413.51	F(000) = 440
Triclinic, P1	D_x = 1.269 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4719 (3) Å	Cell parameters from 11428 reflections
b = 10.5057 (3) Å	θ = 3.0–27.6°
c = 11.8110 (4) Å	µ = 0.08 mm⁻¹
α = 96.824 (3)°	T = 100 K
β = 108.953 (4)°	Prism, colourless
γ = 98.312 (3)°	0.32 × 0.25 × 0.22 mm
V = 1082.51 (7) Å³

Data collection top

Rigaku Saturn724+ diffractometer	R_int = 0.043
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 3.1°
Graphite monochromator	h = −12→12
profile data from ω–scans	k = −13→13
13756 measured reflections	l = −15→15
4972 independent reflections	3 standard reflections every 2 min
3736 reflections with I > 2σ(I)	intensity decay: 1%

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) = 0.135	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0577P)² + 0.355P] where P = (F_o² + 2F_c²)/3
4972 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₆H₂₇N₃O₂	γ = 98.312 (3)°
M_r = 413.51	V = 1082.51 (7) Å³
Triclinic, P1	Z = 2
a = 9.4719 (3) Å	Mo Kα radiation
b = 10.5057 (3) Å	µ = 0.08 mm⁻¹
c = 11.8110 (4) Å	T = 100 K
α = 96.824 (3)°	0.32 × 0.25 × 0.22 mm
β = 108.953 (4)°

Data collection top

Rigaku Saturn724+ diffractometer	R_int = 0.043
13756 measured reflections	3 standard reflections every 2 min
4972 independent reflections	intensity decay: 1%
3736 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	Δρ_max = 0.63 e Å⁻³
4972 reflections	Δρ_min = −0.24 e Å⁻³
280 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.28084 (13)	0.57424 (10)	0.27381 (10)	0.0245 (3)
O2	−0.08746 (15)	−0.09871 (11)	−0.38295 (11)	0.0336 (3)
N1	0.18512 (16)	0.52783 (12)	0.47120 (12)	0.0239 (3)
N2	0.28757 (19)	0.70971 (13)	0.61301 (13)	0.0312 (3)
N3	0.03315 (15)	0.10262 (12)	−0.17348 (11)	0.0203 (3)
C1	0.24066 (19)	0.44368 (15)	0.28999 (14)	0.0240 (3)
H1	0.3308	0.4185	0.3444	0.029*
C2	0.12280 (19)	0.44506 (15)	0.35127 (14)	0.0243 (3)
H2A	0.0368	0.4768	0.3008	0.029*
H2B	0.0864	0.3566	0.3593	0.029*
C3	0.2357 (2)	0.65983 (15)	0.49714 (15)	0.0296 (4)
H3	0.2334	0.7103	0.4372	0.036*
C4	0.20304 (18)	0.48813 (15)	0.58148 (13)	0.0211 (3)
C5	0.16909 (19)	0.36691 (15)	0.61283 (14)	0.0240 (3)
H5	0.1268	0.2914	0.5544	0.029*
C6	0.2014 (2)	0.36446 (16)	0.73509 (15)	0.0288 (4)
H6	0.1793	0.2854	0.7596	0.035*
C7	0.2668 (2)	0.47816 (17)	0.82337 (15)	0.0303 (4)
H7	0.2874	0.4726	0.9050	0.036*
C8	0.3011 (2)	0.59754 (16)	0.79188 (15)	0.0298 (4)
H8	0.3452	0.6724	0.8509	0.036*
C9	0.26797 (19)	0.60318 (15)	0.66909 (15)	0.0244 (3)
C10	0.4207 (2)	0.59640 (17)	0.25038 (18)	0.0319 (4)
H10A	0.4128	0.5376	0.1778	0.038*
H10B	0.5034	0.5810	0.3182	0.038*
C11	0.45016 (18)	0.73490 (16)	0.23337 (15)	0.0253 (3)
C12	0.5176 (2)	0.83670 (17)	0.33221 (16)	0.0313 (4)
H12	0.5461	0.8184	0.4108	0.038*
C13	0.5426 (2)	0.96468 (17)	0.31489 (16)	0.0317 (4)
H13	0.5868	1.0319	0.3817	0.038*
C14	0.5024 (2)	0.99292 (17)	0.19901 (16)	0.0293 (4)
H14	0.5206	1.0789	0.1874	0.035*
C15	0.4350 (2)	0.89280 (18)	0.10032 (16)	0.0320 (4)
H15	0.4065	0.9114	0.0219	0.038*
C16	0.4096 (2)	0.76504 (17)	0.11782 (16)	0.0303 (4)
H16	0.3645	0.6982	0.0507	0.036*
C17	0.18236 (19)	0.34981 (15)	0.17011 (14)	0.0224 (3)
C18	0.0535 (2)	0.36116 (17)	0.07608 (16)	0.0307 (4)
H18	−0.0005	0.4254	0.0888	0.037*
C19	0.0033 (2)	0.27977 (17)	−0.03558 (15)	0.0296 (4)
H19	−0.0826	0.2910	−0.0968	0.036*
C20	0.07978 (18)	0.18079 (14)	−0.05807 (13)	0.0199 (3)
C21	0.2087 (2)	0.16989 (17)	0.03657 (16)	0.0326 (4)
H21	0.2625	0.1051	0.0250	0.039*
C22	0.2586 (2)	0.25367 (17)	0.14774 (15)	0.0320 (4)
H22	0.3459	0.2444	0.2087	0.038*
C23	−0.1301 (2)	0.06684 (18)	−0.24194 (16)	0.0332 (4)
H23A	−0.1756	0.1436	−0.2386	0.040*
H23B	−0.1772	0.0031	−0.2055	0.040*
C24	−0.1588 (2)	0.0102 (2)	−0.37283 (17)	0.0406 (5)
H24A	−0.2675	−0.0169	−0.4157	0.049*
H24B	−0.1206	0.0772	−0.4112	0.049*
C25	0.0716 (2)	−0.05690 (18)	−0.32175 (16)	0.0332 (4)
H25A	0.1098	0.0112	−0.3590	0.040*
H25B	0.1220	−0.1297	−0.3305	0.040*
C26	0.1096 (2)	−0.00560 (17)	−0.18839 (15)	0.0296 (4)
H26A	0.0774	−0.0750	−0.1495	0.036*
H26B	0.2187	0.0238	−0.1497	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0256 (6)	0.0211 (6)	0.0273 (6)	0.0030 (5)	0.0113 (5)	0.0010 (5)
O2	0.0349 (7)	0.0277 (6)	0.0291 (7)	0.0044 (5)	0.0054 (5)	−0.0115 (5)
N1	0.0350 (8)	0.0173 (6)	0.0204 (7)	0.0025 (5)	0.0133 (6)	−0.0004 (5)
N2	0.0486 (10)	0.0190 (7)	0.0279 (8)	0.0018 (6)	0.0198 (7)	−0.0012 (6)
N3	0.0219 (7)	0.0198 (6)	0.0177 (6)	0.0028 (5)	0.0071 (5)	−0.0013 (5)
C1	0.0287 (9)	0.0198 (8)	0.0213 (8)	0.0024 (6)	0.0085 (6)	−0.0009 (6)
C2	0.0298 (9)	0.0210 (8)	0.0210 (8)	0.0004 (6)	0.0110 (7)	−0.0011 (6)
C3	0.0475 (11)	0.0171 (8)	0.0273 (9)	0.0044 (7)	0.0188 (8)	0.0010 (6)
C4	0.0234 (8)	0.0207 (7)	0.0199 (7)	0.0027 (6)	0.0108 (6)	−0.0006 (6)
C5	0.0273 (9)	0.0186 (7)	0.0249 (8)	−0.0005 (6)	0.0116 (7)	−0.0013 (6)
C6	0.0368 (10)	0.0241 (8)	0.0286 (9)	0.0022 (7)	0.0164 (7)	0.0058 (7)
C7	0.0373 (10)	0.0336 (9)	0.0202 (8)	0.0032 (8)	0.0127 (7)	0.0023 (7)
C8	0.0371 (10)	0.0252 (8)	0.0238 (8)	−0.0011 (7)	0.0129 (7)	−0.0056 (7)
C9	0.0285 (9)	0.0186 (8)	0.0263 (8)	0.0003 (6)	0.0136 (7)	−0.0019 (6)
C10	0.0268 (9)	0.0280 (9)	0.0419 (10)	0.0021 (7)	0.0153 (8)	0.0044 (7)
C11	0.0181 (8)	0.0262 (8)	0.0312 (9)	0.0023 (6)	0.0099 (6)	0.0019 (7)
C12	0.0299 (9)	0.0330 (9)	0.0247 (9)	0.0044 (7)	0.0030 (7)	0.0025 (7)
C13	0.0273 (9)	0.0262 (9)	0.0334 (9)	0.0015 (7)	0.0044 (7)	−0.0040 (7)
C14	0.0246 (9)	0.0249 (8)	0.0403 (10)	0.0046 (7)	0.0134 (7)	0.0067 (7)
C15	0.0344 (10)	0.0351 (10)	0.0295 (9)	0.0070 (8)	0.0145 (8)	0.0070 (7)
C16	0.0308 (10)	0.0303 (9)	0.0277 (9)	−0.0011 (7)	0.0135 (7)	−0.0041 (7)
C17	0.0260 (8)	0.0205 (7)	0.0200 (8)	−0.0010 (6)	0.0109 (6)	−0.0007 (6)
C18	0.0289 (9)	0.0310 (9)	0.0301 (9)	0.0102 (7)	0.0097 (7)	−0.0063 (7)
C19	0.0247 (9)	0.0345 (9)	0.0258 (9)	0.0096 (7)	0.0054 (7)	−0.0044 (7)
C20	0.0229 (8)	0.0178 (7)	0.0186 (7)	0.0002 (6)	0.0093 (6)	0.0004 (6)
C21	0.0371 (10)	0.0304 (9)	0.0267 (9)	0.0168 (8)	0.0050 (7)	−0.0036 (7)
C22	0.0345 (10)	0.0326 (9)	0.0221 (8)	0.0122 (8)	0.0010 (7)	−0.0023 (7)
C23	0.0263 (9)	0.0376 (10)	0.0288 (9)	0.0067 (8)	0.0055 (7)	−0.0090 (7)
C24	0.0395 (11)	0.0433 (11)	0.0270 (9)	0.0153 (9)	−0.0011 (8)	−0.0123 (8)
C25	0.0326 (10)	0.0333 (9)	0.0296 (9)	0.0076 (8)	0.0102 (7)	−0.0097 (7)
C26	0.0302 (9)	0.0279 (9)	0.0265 (9)	0.0099 (7)	0.0061 (7)	−0.0057 (7)

Geometric parameters (Å, º) top

O1—C1	1.4218 (19)	C11—C12	1.391 (2)
O1—C10	1.432 (2)	C12—H12	0.9300
O2—C24	1.423 (2)	C13—C12	1.382 (2)
O2—C25	1.418 (2)	C13—H13	0.9300
N1—C2	1.4584 (19)	C14—C13	1.377 (3)
N1—C3	1.363 (2)	C14—C15	1.380 (2)
N1—C4	1.380 (2)	C14—H14	0.9300
N2—C3	1.307 (2)	C15—H15	0.9300
N2—C9	1.386 (2)	C16—C11	1.381 (2)
N3—C20	1.4020 (18)	C16—C15	1.381 (2)
N3—C23	1.461 (2)	C16—H16	0.9300
N3—C26	1.4562 (19)	C17—C18	1.389 (2)
C1—C2	1.516 (2)	C17—C22	1.372 (2)
C1—C17	1.512 (2)	C18—H18	0.9300
C1—H1	0.9800	C19—C18	1.380 (2)
C2—H2A	0.9700	C19—H19	0.9300
C2—H2B	0.9700	C20—C19	1.398 (2)
C3—H3	0.9300	C20—C21	1.392 (2)
C5—C4	1.390 (2)	C21—H21	0.9300
C5—C6	1.380 (2)	C22—C21	1.387 (2)
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.510 (2)
C7—C6	1.403 (2)	C23—H23A	0.9700
C7—H7	0.9300	C23—H23B	0.9700
C8—C7	1.374 (2)	C24—H24A	0.9700
C8—C9	1.391 (2)	C24—H24B	0.9700
C8—H8	0.9300	C25—H25A	0.9700
C9—C4	1.409 (2)	C25—H25B	0.9700
C10—H10A	0.9700	C26—C25	1.508 (2)
C10—H10B	0.9700	C26—H26A	0.9700
C11—C10	1.491 (2)	C26—H26B	0.9700

C1—O1—C10	112.15 (12)	C12—C13—H13	119.9
C25—O2—C24	108.49 (13)	C14—C13—C12	120.23 (16)
C3—N1—C2	127.13 (14)	C14—C13—H13	119.9
C3—N1—C4	106.11 (13)	C13—C14—C15	119.58 (16)
C4—N1—C2	126.76 (13)	C13—C14—H14	120.2
C3—N2—C9	104.06 (13)	C15—C14—H14	120.2
C20—N3—C23	117.52 (12)	C14—C15—C16	120.10 (16)
C20—N3—C26	118.08 (13)	C14—C15—H15	119.9
C26—N3—C23	111.50 (13)	C16—C15—H15	119.9
O1—C1—C2	106.14 (12)	C11—C16—H16	119.5
O1—C1—C17	111.26 (12)	C15—C16—C11	121.07 (16)
O1—C1—H1	108.9	C15—C16—H16	119.5
C2—C1—H1	108.9	C18—C17—C1	121.39 (14)
C17—C1—C2	112.51 (13)	C22—C17—C1	121.31 (15)
C17—C1—H1	108.9	C22—C17—C18	117.24 (14)
N1—C2—C1	111.66 (13)	C17—C18—H18	119.1
N1—C2—H2A	109.3	C19—C18—C17	121.85 (15)
N1—C2—H2B	109.3	C19—C18—H18	119.1
C1—C2—H2A	109.3	C18—C19—C20	120.98 (16)
C1—C2—H2B	109.3	C18—C19—H19	119.5
H2A—C2—H2B	107.9	C20—C19—H19	119.5
N1—C3—H3	122.7	C19—C20—N3	120.82 (14)
N2—C3—N1	114.56 (15)	C21—C20—N3	122.19 (14)
N2—C3—H3	122.7	C21—C20—C19	116.86 (14)
N1—C4—C5	132.71 (14)	C20—C21—H21	119.3
N1—C4—C9	104.98 (13)	C22—C21—C20	121.35 (15)
C5—C4—C9	122.31 (14)	C22—C21—H21	119.3
C4—C5—H5	121.7	C17—C22—C21	121.70 (16)
C6—C5—C4	116.56 (14)	C17—C22—H22	119.1
C6—C5—H5	121.7	C21—C22—H22	119.1
C5—C6—C7	121.73 (16)	N3—C23—C24	110.50 (14)
C5—C6—H6	119.1	N3—C23—H23A	109.5
C7—C6—H6	119.1	N3—C23—H23B	109.5
C6—C7—H7	119.3	C24—C23—H23A	109.5
C8—C7—C6	121.44 (15)	C24—C23—H23B	109.5
C8—C7—H7	119.3	H23A—C23—H23B	108.1
C7—C8—C9	118.07 (15)	O2—C24—C23	112.00 (15)
C7—C8—H8	121.0	O2—C24—H24A	109.2
C9—C8—H8	121.0	O2—C24—H24B	109.2
N2—C9—C4	110.28 (14)	C23—C24—H24A	109.2
N2—C9—C8	129.83 (15)	C23—C24—H24B	109.2
C8—C9—C4	119.89 (15)	H24A—C24—H24B	107.9
O1—C10—C11	107.45 (13)	O2—C25—C26	111.75 (14)
O1—C10—H10A	110.2	O2—C25—H25A	109.3
O1—C10—H10B	110.2	O2—C25—H25B	109.3
C11—C10—H10A	110.2	C26—C25—H25A	109.3
C11—C10—H10B	110.2	C26—C25—H25B	109.3
H10A—C10—H10B	108.5	H25A—C25—H25B	107.9
C12—C11—C10	121.43 (16)	N3—C26—C25	110.05 (14)
C16—C11—C10	120.25 (15)	N3—C26—H26A	109.6
C16—C11—C12	118.32 (16)	N3—C26—H26B	109.6
C11—C12—H12	119.7	C25—C26—H26A	109.6
C13—C12—C11	120.70 (16)	C25—C26—H26B	109.7
C13—C12—H12	119.7	H26A—C26—H26B	108.2

C10—O1—C1—C2	162.84 (13)	C4—C5—C6—C7	−0.7 (3)
C10—O1—C1—C17	−74.46 (17)	C8—C7—C6—C5	0.3 (3)
C1—O1—C10—C11	179.24 (13)	C9—C8—C7—C6	0.5 (3)
C25—O2—C24—C23	−59.9 (2)	C7—C8—C9—N2	178.51 (17)
C24—O2—C25—C26	60.96 (19)	C7—C8—C9—C4	−0.8 (3)
C3—N1—C2—C1	64.8 (2)	N2—C9—C4—N1	0.47 (18)
C4—N1—C2—C1	−116.02 (17)	N2—C9—C4—C5	−179.06 (15)
C2—N1—C3—N2	−179.33 (16)	C8—C9—C4—N1	179.93 (15)
C4—N1—C3—N2	1.4 (2)	C8—C9—C4—C5	0.4 (2)
C2—N1—C4—C5	−0.9 (3)	C12—C11—C10—O1	82.65 (19)
C2—N1—C4—C9	179.66 (15)	C16—C11—C10—O1	−96.93 (18)
C3—N1—C4—C5	178.42 (18)	C10—C11—C12—C13	−179.33 (16)
C3—N1—C4—C9	−1.04 (17)	C16—C11—C12—C13	0.3 (3)
C9—N2—C3—N1	−1.0 (2)	C14—C13—C12—C11	−0.7 (3)
C3—N2—C9—C4	0.32 (19)	C15—C14—C13—C12	0.9 (3)
C3—N2—C9—C8	−179.07 (18)	C13—C14—C15—C16	−0.7 (3)
C23—N3—C20—C19	−36.8 (2)	C15—C16—C11—C10	179.54 (16)
C23—N3—C20—C21	147.48 (17)	C15—C16—C11—C12	0.0 (3)
C26—N3—C20—C19	−175.07 (15)	C11—C16—C15—C14	0.3 (3)
C26—N3—C20—C21	9.2 (2)	C1—C17—C18—C19	176.97 (16)
C20—N3—C23—C24	167.07 (14)	C22—C17—C18—C19	−0.1 (3)
C26—N3—C23—C24	−52.07 (19)	C1—C17—C22—C21	−177.82 (17)
C20—N3—C26—C25	−166.46 (14)	C18—C17—C22—C21	−0.8 (3)
C23—N3—C26—C25	52.92 (19)	C20—C19—C18—C17	0.9 (3)
O1—C1—C2—N1	−62.84 (16)	N3—C20—C19—C18	−176.71 (16)
C17—C1—C2—N1	175.25 (13)	C21—C20—C19—C18	−0.8 (3)
O1—C1—C17—C18	−60.9 (2)	N3—C20—C21—C22	175.82 (16)
O1—C1—C17—C22	116.07 (17)	C19—C20—C21—C22	−0.1 (3)
C2—C1—C17—C18	58.1 (2)	C17—C22—C21—C20	0.8 (3)
C2—C1—C17—C22	−124.97 (17)	N3—C23—C24—O2	56.1 (2)
C6—C5—C4—N1	−179.01 (17)	N3—C26—C25—O2	−58.1 (2)
C6—C5—C4—C9	0.4 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C4–C9 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.93	2.58	3.478 (2)	163
C6—H6···N3ⁱⁱ	0.93	2.56	3.439 (2)	159
C2—H2A···Cgⁱⁱⁱ	0.97	2.66	3.451 (2)	139

Symmetry codes: (i) −x, −y, −z; (ii) x, y, z+1; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₇N₃O₂
M_r	413.51
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.4719 (3), 10.5057 (3), 11.8110 (4)
α, β, γ (°)	96.824 (3), 108.953 (4), 98.312 (3)
V (Å³)	1082.51 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.25 × 0.22

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13756, 4972, 3736
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.135, 1.06
No. of reflections	4972
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.24

Computer programs: CrystalClear-SM Expert (Rigaku, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C4–C9 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.93	2.58	3.478 (2)	163
C6—H6···N3ⁱⁱ	0.93	2.56	3.439 (2)	159
C2—H2A···Cgⁱⁱⁱ	0.97	2.66	3.451 (2)	139

Symmetry codes: (i) −x, −y, −z; (ii) x, y, z+1; (iii) −x, −y+1, −z+1.

Acknowledgements

The authors are grateful to Zonguldak Karaelmas University Research Fund (project No. 2010-13-02-06).

References

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