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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 7| July 2013| Page o1022
https://doi.org/10.1107/S1600536813014670

2-Methyl-1,1-di­phenyl-2-[(4S)-4-phenyl-4,5-di­hydro-1,3-oxazol-2-yl]propan-1-ol

Wen-Xiao Jia,a Yu-Lai Hu,a* Dang-Feng Huang,a Teng Niua and Yan-Jun Maa

aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu Province 730070, People's Republic of China
*Correspondence e-mail: huylai@163.com

(Received 22 March 2013; accepted 28 May 2013; online 8 June 2013)

In the title compound, C25H25NO2, the phenyl ring on the 1,3-oxazole ring is disordered over two positions with occupancies of 0.600 (4) and 0.400 (4). The inter­planar angle between these two disordered rings is 77.8 (2)°. There is an intra­molecular O—H⋯N hydrogen bond of moderate strength. In the crystal, C—H⋯π inter­actions interconnect neighbouring molecules. The absolute structure has been derived from the known absolute structure of the reagents.

Related literature

For the synthesis and applications of oxazolines, see: Ghosh et al. (1998[Ghosh, A. K., Mathivanan, P. & Cappiello, J. (1998). Tetrahedron Asymmetry, 9, 1-45.]); Johnson & Evans (2000[Johnson, J. S. & Evans, D. A. (2000). Acc. Chem. Res. 33, 325-335.]). For the categorization of hydrogen bonds, see: Gilli & Gilli (2009[Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond. Outline of a Comprehensive Hydrogen Bond Theory, p. 61. International Union of Crystallography. Oxford Science Publications. New York, Oxford: Oxford University Press Inc.]).

[Scheme 1]

Experimental

Crystal data

  • C25H25NO2

  • Mr = 371.46

  • Orthorhombic, P 21 21 21

  • a = 9.5405 (2) Å

  • b = 10.9430 (9) Å

  • c = 19.2901 (6) Å

  • V = 2013.92 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.34 × 0.07 × 0.06 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.849, Tmax = 0.977

  • 5590 measured reflections

  • 2428 independent reflections

  • 2103 reflections with I > 2σ(I)

  • Rint = 0.040
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.102

  • S = 1.08

  • 2428 reflections

  • 305 parameters

  • 338 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C8–C13, C14–C19 and C20–C25 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯N6 0.86 (3) 1.89 (3) 2.712 (3) 159 (3)
C1—H1⋯Cg2i 0.98 2.80 3.771 (3) 173
C2—H2A⋯Cg2ii 0.97 2.86 3.589 (3) 132
C24B—H24B⋯Cg3iii 0.93 2.87 3.776 (6) 166
C24B—H24B⋯Cg4iii 0.93 2.97 3.785 (9) 147
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x-1, y, z; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813014670/fb2285sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813014670/fb2285Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813014670/fb2285Isup3.cml

checkCIF report


Comment top

Over the last decade, C2-symmetric chiral oxazoline metal complexes have been recognized as an effective class of chiral catalyst in a variety of transition metal catalyzed asymmetric reactions. Thus, the design and synthesis of new chiral oxazoline ligands has inspired many scientists to work with great efforts (Ghosh et al., 1998, Johnson & Evans, 2000).

The title compound (Fig. 1) is a new oxazoline ligand, (S)-2-methyl-1,1-diphenyl-2-(4-phenyl-4,5-dihydrooxazol-2-yl propan-1-ol), which has been designed as a potential ligand for asymmetric catalysis. It combines diphenyl methyl units and chiral oxazoline ring together with dimethyl methyl malonate.

Fig. 2 shows the packing of the molecules in the title structure.

Peculiarity of the title crystal structure is presence of a disorder which affects one of the phenyl rings which is split into two positions: C20//C21a//C22a//C23a//C24a//C25a and C20//C21b//C22b//C23b//C24b//C25b, the respective occupations of which are 0.600 (4) and 0.400 (4). The interplanar angle of both disordered rings equals to 77.8 (2)°.

There is an intramolecular hydrogen bond O2—H2···N6 of moderate strength in the structure (Tab. 1). (For categorization of the hydrogen bonds, see Gilli & Gilli, 2009.) There are present C—H···π-electron ring interactions in the structure (Tab. 1), too.

Related literature top

For the synthesis and applications of oxazolines, see: Ghosh et al. (1998); Johnson & Evans (2000). For the categorization of hydrogen bonds, see: Gilli & Gilli (2009).

Experimental top

Mono(oxazoline) (0.5 g, 2 mmol) dissolved in 10 ml of tetrahydrofuran was placed into a two-neck 50 ml round-bottom flask that had been previously dried and that was equipped with a magnetic stirrer and a nitrogen inlet. The solution was cooled to 273 K and phenylmagnesium bromide (1.4 g, 8 mmol) which had been dissolved in 2 ml of tetrahydrofuran was added dropwise under nitrogen atmosphere to the solution of monoxazoline in tetrahydrofuran. The reaction mixture was stirred for 2 h at the same temperature. Then thin layer chromatography showed that the raw material had disappeared and indicated completion of the reaction. In the following step, 15 ml of saturated NH4Cl was added into the reaction solution at 273 K. The product was extracted by ethyl acetate (3×10 ml). The combined ethyl acetate extracts were dried over Na2SO4. The residue obtained after the evaporation of the solvent was purified by silica gel column chromatography with petroleum ether. The crude product was dissolved in 1 ml petroleum ether and the crystals were recrystallized after 4 hours in 55% yield as white or colourless needles typically 2-3 mm long and 0.5 mm wide. Melting point: 380-381 K (determined by a X-4 digital display microscopic melting-point apparatus).

Refinement top

The H atoms which have not been involved in the disordered phenyl rings were discernible in the difference electron density maps. The H atoms which were attached to the carbons were situated into the idealized positions and constrained using the following constraints: Caryl—Haryl = 0.93; Cmethyl—Hmethyl = 0.96; Cmethylene—Hmethylene = 0.97; Cmethine—Hmethine = 0.98 Å. UisoHaryl = 1.2UeqCaryl; UisoHmethyl = 1.5UeqCmethyl; UisoHmethylene = 1.2UeqCmethylene; UisoHmethine = 1.2UeqCmethine. The positional parameters of the hydroxyl hydrogen were freely refined while UisoHhydroxyl = 1.5UeqOhydroxyl. The occupational parameters of the disoredered phenyl rings were constrained in such a way that the their sum equalled to 1. The displacement parameters of the corresponding disordered atoms C21a, C21b ··· C25a, C25b were restrained by the command ISOR 0.01 0.02 and SIMU_* (SHELXL97, Sheldrick, 2008). In absence of significant resonant scatterers 1284 Friedel pairs have been merged by application of the command MERG 3 [SHELXL97 (Sheldrick, 2008)].

Structure description top

Over the last decade, C2-symmetric chiral oxazoline metal complexes have been recognized as an effective class of chiral catalyst in a variety of transition metal catalyzed asymmetric reactions. Thus, the design and synthesis of new chiral oxazoline ligands has inspired many scientists to work with great efforts (Ghosh et al., 1998, Johnson & Evans, 2000).

The title compound (Fig. 1) is a new oxazoline ligand, (S)-2-methyl-1,1-diphenyl-2-(4-phenyl-4,5-dihydrooxazol-2-yl propan-1-ol), which has been designed as a potential ligand for asymmetric catalysis. It combines diphenyl methyl units and chiral oxazoline ring together with dimethyl methyl malonate.

Fig. 2 shows the packing of the molecules in the title structure.

Peculiarity of the title crystal structure is presence of a disorder which affects one of the phenyl rings which is split into two positions: C20//C21a//C22a//C23a//C24a//C25a and C20//C21b//C22b//C23b//C24b//C25b, the respective occupations of which are 0.600 (4) and 0.400 (4). The interplanar angle of both disordered rings equals to 77.8 (2)°.

There is an intramolecular hydrogen bond O2—H2···N6 of moderate strength in the structure (Tab. 1). (For categorization of the hydrogen bonds, see Gilli & Gilli, 2009.) There are present C—H···π-electron ring interactions in the structure (Tab. 1), too.

For the synthesis and applications of oxazolines, see: Ghosh et al. (1998); Johnson & Evans (2000). For the categorization of hydrogen bonds, see: Gilli & Gilli (2009).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The title molecule with the atomic labelling scheme. The displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title molecules viewed approximately along the a axis.
2-Methyl-1,1-diphenyl-2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-1-ol top
Crystal data top
C25H25NO2Dx = 1.225 Mg m−3
Mr = 371.46Melting point = 380–381 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2137 reflections
a = 9.5405 (2) Åθ = 3.0–28.6°
b = 10.9430 (9) ŵ = 0.08 mm−1
c = 19.2901 (6) ÅT = 293 K
V = 2013.92 (18) Å3Block, colourless
Z = 40.34 × 0.07 × 0.06 mm
F(000) = 792
Data collection top
Bruker APEXII CCD
diffractometer		2428 independent reflections
Radiation source: fine-focus sealed tube2103 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 26.8°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −12→4
Tmin = 0.849, Tmax = 0.977k = −10→13
5590 measured reflectionsl = −24→21
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0298P)2 + 0.5879P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2428 reflectionsΔρmax = 0.21 e Å−3
305 parametersΔρmin = −0.17 e Å−3
338 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
114 constraintsExtinction coefficient: 0.0119 (14)
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H25NO2V = 2013.92 (18) Å3
Mr = 371.46Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.5405 (2) ŵ = 0.08 mm−1
b = 10.9430 (9) ÅT = 293 K
c = 19.2901 (6) Å0.34 × 0.07 × 0.06 mm
Data collection top
Bruker APEXII CCD
diffractometer		2428 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		2103 reflections with I > 2σ(I)
Tmin = 0.849, Tmax = 0.977Rint = 0.040
5590 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045338 restraints
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.21 e Å−3
2428 reflectionsΔρmin = −0.17 e Å−3
305 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
xyzUiso*/UeqOcc. (<1)
O10.28330 (17)0.33991 (18)0.16867 (10)0.0264 (5)
O20.68088 (19)0.51237 (16)0.19226 (9)0.0183 (4)
H20.596 (3)0.533 (3)0.1828 (15)0.027*
C140.6840 (3)0.3818 (2)0.09158 (12)0.0183 (5)
C30.4060 (3)0.4020 (2)0.17253 (12)0.0176 (5)
C150.8082 (3)0.4282 (3)0.06375 (13)0.0256 (6)
H150.87700.45790.09350.031*
N60.4060 (2)0.5148 (2)0.15641 (10)0.0196 (5)
C130.8502 (3)0.2144 (2)0.17551 (13)0.0214 (6)
H130.80970.18240.13560.026*
C80.7957 (2)0.3207 (2)0.20445 (12)0.0171 (5)
C111.0271 (3)0.2014 (3)0.26401 (14)0.0266 (6)
H111.10420.16230.28350.032*
C120.9640 (3)0.1553 (3)0.20530 (13)0.0239 (6)
H120.99800.08380.18540.029*
C100.9738 (3)0.3071 (3)0.29357 (14)0.0269 (6)
H101.01510.33890.33340.032*
C190.5830 (3)0.3393 (3)0.04617 (13)0.0231 (6)
H190.49870.30900.06320.028*
C160.8312 (3)0.4309 (3)−0.00695 (14)0.0343 (7)
H160.91480.4621−0.02430.041*
C50.6704 (2)0.3861 (2)0.17153 (12)0.0158 (5)
C170.7302 (3)0.3874 (3)−0.05183 (14)0.0335 (7)
H170.74540.3890−0.09940.040*
C90.8593 (3)0.3661 (2)0.26428 (13)0.0213 (6)
H90.82450.43670.28480.026*
C70.5206 (3)0.3499 (3)0.28064 (12)0.0237 (6)
H7A0.53680.43440.29150.036*
H7B0.59020.30040.30300.036*
H7C0.42910.32650.29660.036*
C20.1796 (3)0.4270 (3)0.14409 (15)0.0298 (7)
H2A0.10330.43480.17700.036*
H2B0.14180.40180.09970.036*
C40.5295 (3)0.3314 (2)0.20112 (12)0.0169 (5)
C180.6074 (3)0.3418 (3)−0.02570 (13)0.0304 (7)
H180.53940.3120−0.05580.037*
C10.2605 (3)0.5484 (3)0.13726 (13)0.0205 (6)
H10.22420.60610.17180.025*
C200.2515 (3)0.6070 (3)0.06651 (14)0.0282 (7)
C60.5148 (3)0.1927 (2)0.18810 (13)0.0213 (6)
H6A0.42510.16540.20460.032*
H6B0.58770.15000.21230.032*
H6C0.52230.17660.13930.032*
C21A0.2705 (6)0.5271 (5)0.0051 (2)0.0364 (14)0.600 (4)
H21A0.28750.44400.01070.044*0.600 (4)
C22A0.2626 (6)0.5774 (5)−0.0610 (2)0.0391 (14)0.600 (4)
H22A0.27520.5273−0.09940.047*0.600 (4)
C23A0.2373 (7)0.6970 (6)−0.0704 (3)0.0343 (15)0.600 (4)
H23A0.23310.7297−0.11490.041*0.600 (4)
C24A0.2175 (9)0.7703 (5)−0.0134 (3)0.0521 (19)0.600 (4)
H24A0.19970.8532−0.01920.062*0.600 (4)
C25A0.2240 (7)0.7205 (5)0.0536 (3)0.0458 (16)0.600 (4)
H25A0.20770.77220.09100.055*0.600 (4)
C21B0.3699 (8)0.6581 (8)0.0362 (4)0.036 (2)0.400 (4)
H21B0.45750.64880.05670.044*0.400 (4)
C22B0.3554 (9)0.7233 (8)−0.0252 (4)0.042 (2)0.400 (4)
H22B0.43520.7480−0.04900.050*0.400 (4)
C23B0.2253 (11)0.7519 (10)−0.0514 (5)0.039 (3)0.400 (4)
H23B0.21670.7919−0.09370.046*0.400 (4)
C24B0.1101 (9)0.7207 (8)−0.0144 (4)0.036 (2)0.400 (4)
H24B0.02230.7444−0.03040.043*0.400 (4)
C25B0.1192 (8)0.6542 (7)0.0469 (4)0.0310 (18)0.400 (4)
H25B0.04040.64120.07430.037*0.400 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0155 (8)0.0262 (10)0.0375 (11)−0.0019 (9)−0.0028 (8)0.0104 (9)
O20.0163 (8)0.0146 (8)0.0239 (9)−0.0003 (8)−0.0017 (8)−0.0015 (7)
C140.0205 (12)0.0155 (12)0.0190 (12)0.0054 (12)−0.0007 (11)0.0015 (10)
C30.0157 (11)0.0219 (13)0.0152 (11)−0.0014 (12)0.0009 (10)0.0008 (10)
C150.0225 (12)0.0324 (15)0.0219 (13)0.0034 (14)−0.0003 (11)0.0053 (12)
N60.0182 (10)0.0192 (11)0.0215 (11)0.0021 (10)−0.0019 (9)0.0015 (9)
C130.0220 (12)0.0245 (14)0.0176 (12)0.0033 (12)0.0024 (11)0.0019 (11)
C80.0173 (11)0.0181 (12)0.0158 (11)−0.0014 (11)0.0004 (10)0.0024 (10)
C110.0166 (11)0.0316 (16)0.0315 (14)−0.0022 (14)−0.0026 (12)0.0128 (13)
C120.0235 (12)0.0234 (13)0.0249 (13)0.0060 (13)0.0031 (11)0.0046 (12)
C100.0247 (12)0.0291 (15)0.0270 (13)−0.0044 (14)−0.0074 (12)0.0032 (12)
C190.0263 (13)0.0235 (14)0.0197 (12)0.0000 (13)−0.0006 (11)−0.0004 (11)
C160.0277 (14)0.0450 (19)0.0302 (15)0.0087 (16)0.0110 (13)0.0124 (14)
C50.0165 (11)0.0128 (11)0.0179 (11)−0.0007 (11)−0.0013 (10)−0.0006 (10)
C170.0447 (17)0.0420 (18)0.0138 (13)0.0139 (16)0.0081 (13)0.0005 (12)
C90.0212 (12)0.0198 (13)0.0228 (13)−0.0023 (11)−0.0019 (11)−0.0003 (11)
C70.0245 (12)0.0286 (15)0.0181 (12)0.0015 (14)0.0019 (11)0.0044 (11)
C20.0168 (12)0.0322 (16)0.0403 (16)0.0020 (14)−0.0066 (12)0.0118 (14)
C40.0170 (11)0.0153 (12)0.0184 (12)−0.0004 (12)0.0000 (10)0.0009 (11)
C180.0395 (15)0.0332 (16)0.0187 (13)0.0070 (16)−0.0034 (12)−0.0055 (12)
C10.0164 (11)0.0239 (14)0.0212 (13)0.0029 (12)0.0030 (10)0.0025 (11)
C200.0180 (12)0.0408 (18)0.0257 (14)0.0023 (14)−0.0024 (11)0.0094 (13)
C60.0211 (12)0.0183 (13)0.0244 (13)−0.0014 (12)−0.0031 (11)0.0011 (11)
C21A0.055 (3)0.032 (3)0.022 (2)0.016 (3)−0.005 (2)−0.005 (2)
C22A0.053 (3)0.043 (3)0.021 (2)0.010 (3)−0.002 (2)−0.003 (2)
C23A0.040 (3)0.046 (4)0.017 (3)−0.003 (3)−0.006 (2)0.005 (3)
C24A0.098 (5)0.024 (3)0.035 (3)−0.004 (4)−0.008 (4)0.009 (3)
C25A0.085 (4)0.029 (3)0.023 (2)−0.002 (3)−0.005 (3)−0.002 (2)
C21B0.034 (4)0.045 (4)0.029 (4)−0.004 (4)0.001 (3)0.011 (4)
C22B0.049 (4)0.048 (5)0.029 (4)−0.013 (4)−0.001 (4)0.016 (4)
C23B0.062 (5)0.041 (6)0.013 (4)0.004 (5)0.007 (4)0.007 (4)
C24B0.039 (4)0.037 (4)0.033 (4)0.010 (4)−0.006 (3)0.017 (3)
C25B0.031 (3)0.036 (4)0.027 (3)−0.003 (4)−0.006 (3)0.001 (3)
Geometric parameters (Å, º) top
O1—C31.355 (3)C7—H7C0.9600
O1—C21.453 (3)C2—C11.542 (4)
O2—C51.442 (3)C2—H2A0.9700
O2—H20.86 (3)C2—H2B0.9700
C14—C191.383 (4)C4—C61.545 (3)
C14—C151.396 (4)C18—H180.9300
C14—C51.548 (3)C1—C201.510 (4)
C3—N61.274 (3)C1—H10.9800
C3—C41.513 (3)C20—C25A1.293 (6)
C15—C161.382 (4)C20—C21B1.390 (8)
C15—H150.9300C20—C25B1.415 (7)
N6—C11.483 (3)C20—C21A1.483 (5)
C13—C121.388 (4)C6—H6A0.9600
C13—C81.391 (4)C6—H6B0.9600
C13—H130.9300C6—H6C0.9600
C8—C91.395 (3)C21A—C22A1.391 (6)
C8—C51.531 (3)C21A—H21A0.9300
C11—C121.379 (4)C22A—C23A1.343 (8)
C11—C101.387 (4)C22A—H22A0.9300
C11—H110.9300C23A—C24A1.375 (8)
C12—H120.9300C23A—H23A0.9300
C10—C91.389 (4)C24A—C25A1.403 (7)
C10—H100.9300C24A—H24A0.9300
C19—C181.406 (4)C25A—H25A0.9300
C19—H190.9300C21B—C22B1.389 (9)
C16—C171.380 (4)C21B—H21B0.9300
C16—H160.9300C22B—C23B1.377 (12)
C5—C41.578 (3)C22B—H22B0.9300
C17—C181.370 (4)C23B—C24B1.355 (11)
C17—H170.9300C23B—H23B0.9300
C9—H90.9300C24B—C25B1.391 (9)
C7—C41.549 (3)C24B—H24B0.9300
C7—H7A0.9600C25B—H25B0.9300
C7—H7B0.9600
C3—O1—C2106.09 (19)C6—C4—C7106.5 (2)
C5—O2—H298 (2)C3—C4—C5109.78 (19)
C19—C14—C15118.0 (2)C6—C4—C5113.0 (2)
C19—C14—C5125.6 (2)C7—C4—C5110.8 (2)
C15—C14—C5116.3 (2)C17—C18—C19120.8 (3)
N6—C3—O1118.2 (2)C17—C18—H18119.6
N6—C3—C4125.7 (2)C19—C18—H18119.6
O1—C3—C4115.9 (2)N6—C1—C20112.5 (2)
C16—C15—C14121.5 (3)N6—C1—C2103.5 (2)
C16—C15—H15119.3C20—C1—C2114.5 (2)
C14—C15—H15119.3N6—C1—H1108.7
C3—N6—C1107.5 (2)C20—C1—H1108.7
C12—C13—C8121.0 (2)C2—C1—H1108.7
C12—C13—H13119.5C25A—C20—C21B72.4 (5)
C8—C13—H13119.5C25A—C20—C25B54.4 (4)
C13—C8—C9117.8 (2)C21B—C20—C25B117.8 (4)
C13—C8—C5121.1 (2)C25A—C20—C21A115.9 (4)
C9—C8—C5121.1 (2)C21B—C20—C21A78.6 (4)
C12—C11—C10118.9 (2)C25B—C20—C21A96.3 (4)
C12—C11—H11120.6C25A—C20—C1126.4 (3)
C10—C11—H11120.6C21B—C20—C1120.3 (4)
C11—C12—C13120.8 (3)C25B—C20—C1116.6 (4)
C11—C12—H12119.6C21A—C20—C1117.7 (3)
C13—C12—H12119.6C4—C6—H6A109.5
C11—C10—C9120.6 (3)C4—C6—H6B109.5
C11—C10—H10119.7H6A—C6—H6B109.5
C9—C10—H10119.7C4—C6—H6C109.5
C14—C19—C18120.2 (3)H6A—C6—H6C109.5
C14—C19—H19119.9H6B—C6—H6C109.5
C18—C19—H19119.9C22A—C21A—C20119.5 (4)
C17—C16—C15120.0 (3)C22A—C21A—H21A120.2
C17—C16—H16120.0C20—C21A—H21A120.2
C15—C16—H16120.0C23A—C22A—C21A121.3 (5)
O2—C5—C8106.15 (19)C23A—C22A—H22A119.4
O2—C5—C14107.39 (19)C21A—C22A—H22A119.4
C8—C5—C14109.5 (2)C22A—C23A—C24A119.0 (5)
O2—C5—C4108.78 (19)C22A—C23A—H23A120.5
C8—C5—C4109.78 (18)C24A—C23A—H23A120.5
C14—C5—C4114.86 (19)C23A—C24A—C25A120.3 (5)
C18—C17—C16119.5 (2)C23A—C24A—H24A119.9
C18—C17—H17120.3C25A—C24A—H24A119.9
C16—C17—H17120.3C20—C25A—C24A124.0 (5)
C10—C9—C8120.9 (2)C20—C25A—H25A118.0
C10—C9—H9119.5C24A—C25A—H25A118.0
C8—C9—H9119.5C22B—C21B—C20118.9 (6)
C4—C7—H7A109.5C22B—C21B—H21B120.5
C4—C7—H7B109.5C20—C21B—H21B120.5
H7A—C7—H7B109.5C23B—C22B—C21B121.4 (7)
C4—C7—H7C109.5C23B—C22B—H22B119.3
H7A—C7—H7C109.5C21B—C22B—H22B119.3
H7B—C7—H7C109.5C24B—C23B—C22B118.7 (8)
O1—C2—C1104.63 (19)C24B—C23B—H23B120.7
O1—C2—H2A110.8C22B—C23B—H23B120.7
C1—C2—H2A110.8C23B—C24B—C25B122.0 (8)
O1—C2—H2B110.8C23B—C24B—H24B119.0
C1—C2—H2B110.8C25B—C24B—H24B119.0
H2A—C2—H2B108.9C24B—C25B—C20118.3 (6)
C3—C4—C6111.8 (2)C24B—C25B—H25B120.9
C3—C4—C7104.6 (2)C20—C25B—H25B120.9
C2—O1—C3—N61.0 (3)C14—C5—C4—C665.4 (3)
C2—O1—C3—C4176.6 (2)O2—C5—C4—C7−54.8 (3)
C19—C14—C15—C16−0.6 (4)C8—C5—C4—C761.0 (3)
C5—C14—C15—C16−179.0 (3)C14—C5—C4—C7−175.2 (2)
O1—C3—N6—C10.6 (3)C16—C17—C18—C190.3 (5)
C4—C3—N6—C1−174.6 (2)C14—C19—C18—C17−0.8 (4)
C12—C13—C8—C90.1 (4)C3—N6—C1—C20−125.9 (2)
C12—C13—C8—C5179.9 (2)C3—N6—C1—C2−1.8 (3)
C10—C11—C12—C130.9 (4)O1—C2—C1—N62.3 (3)
C8—C13—C12—C11−0.8 (4)O1—C2—C1—C20125.2 (2)
C12—C11—C10—C9−0.4 (4)N6—C1—C20—C25A−109.5 (5)
C15—C14—C19—C180.9 (4)C2—C1—C20—C25A132.7 (5)
C5—C14—C19—C18179.2 (3)N6—C1—C20—C21B−19.8 (5)
C14—C15—C16—C170.1 (5)C2—C1—C20—C21B−137.6 (5)
C13—C8—C5—O2−154.6 (2)N6—C1—C20—C25B−173.3 (4)
C9—C8—C5—O225.2 (3)C2—C1—C20—C25B68.9 (5)
C13—C8—C5—C14−38.9 (3)N6—C1—C20—C21A72.9 (4)
C9—C8—C5—C14140.8 (2)C2—C1—C20—C21A−44.9 (4)
C13—C8—C5—C488.0 (3)C25A—C20—C21A—C22A2.0 (7)
C9—C8—C5—C4−92.2 (3)C21B—C20—C21A—C22A−61.8 (6)
C19—C14—C5—O2−118.7 (3)C25B—C20—C21A—C22A55.3 (6)
C15—C14—C5—O259.6 (3)C1—C20—C21A—C22A179.9 (4)
C19—C14—C5—C8126.5 (3)C20—C21A—C22A—C23A−0.4 (9)
C15—C14—C5—C8−55.2 (3)C21A—C22A—C23A—C24A−0.6 (10)
C19—C14—C5—C42.4 (4)C22A—C23A—C24A—C25A0.1 (12)
C15—C14—C5—C4−179.3 (2)C21B—C20—C25A—C24A64.7 (8)
C15—C16—C17—C180.1 (5)C25B—C20—C25A—C24A−81.3 (8)
C11—C10—C9—C8−0.3 (4)C21A—C20—C25A—C24A−2.6 (9)
C13—C8—C9—C100.4 (4)C1—C20—C25A—C24A179.8 (6)
C5—C8—C9—C10−179.4 (2)C23A—C24A—C25A—C201.7 (12)
C3—O1—C2—C1−2.1 (3)C25A—C20—C21B—C22B−50.5 (7)
N6—C3—C4—C6−157.5 (2)C25B—C20—C21B—C22B−19.6 (10)
O1—C3—C4—C627.3 (3)C21A—C20—C21B—C22B71.6 (7)
N6—C3—C4—C787.7 (3)C1—C20—C21B—C22B−172.8 (6)
O1—C3—C4—C7−87.5 (3)C20—C21B—C22B—C23B8.8 (14)
N6—C3—C4—C5−31.2 (3)C21B—C22B—C23B—C24B3.3 (16)
O1—C3—C4—C5153.5 (2)C22B—C23B—C24B—C25B−4.1 (16)
O2—C5—C4—C360.2 (2)C23B—C24B—C25B—C20−7.0 (13)
C8—C5—C4—C3176.0 (2)C25A—C20—C25B—C24B55.8 (7)
C14—C5—C4—C3−60.2 (3)C21B—C20—C25B—C24B18.8 (9)
O2—C5—C4—C6−174.25 (19)C21A—C20—C25B—C24B−61.7 (7)
C8—C5—C4—C6−58.5 (2)C1—C20—C25B—C24B173.0 (6)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C14–C19, C8–C13, C14–C19 and C20–C25 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O2—H2···N60.86 (3)1.89 (3)2.712 (3)159 (3)
C1—H1···Cg2i0.982.803.771 (3)173
C2—H2A···Cg2ii0.972.863.589 (3)132
C21A—H21A···Cg10.932.813.058 (4)97
C24B—H24B···Cg3iii0.932.873.776 (6)166
C24B—H24B···Cg4iii0.932.973.785 (9)147
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formulaC25H25NO2
Mr371.46
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)9.5405 (2), 10.9430 (9), 19.2901 (6)
V (Å3)2013.92 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.34 × 0.07 × 0.06
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.849, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections		5590, 2428, 2103
Rint0.040
(sin θ/λ)max (Å−1)0.633
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.102, 1.08
No. of reflections2428
No. of parameters305
No. of restraints338
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.21, −0.17

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2010), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C14–C19, C8–C13, C14–C19 and C20–C25 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O2—H2···N60.86 (3)1.89 (3)2.712 (3)159 (3)
C1—H1···Cg2i0.98002.803.771 (3)173
C2—H2A···Cg2ii0.97002.863.589 (3)132
C21A—H21A···Cg10.93002.813.058 (4)97
C24B—H24B···Cg3iii0.93002.873.776 (6)166
C24B—H24B···Cg4iii0.93002.973.785 (9)147
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z.
 

Acknowledgements

This work was supported by the Key Laboratory of Polymer Materials of Gansu Province (Northwest Normal University).

References

First citationBrandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationGhosh, A. K., Mathivanan, P. & Cappiello, J. (1998). Tetrahedron Asymmetry, 9, 1–45.  Web of Science CrossRef CAS Google Scholar
 First citationGilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond. Outline of a Comprehensive Hydrogen Bond Theory, p. 61. International Union of Crystallography. Oxford Science Publications. New York, Oxford: Oxford University Press Inc.  Google Scholar
 First citationJohnson, J. S. & Evans, D. A. (2000). Acc. Chem. Res. 33, 325–335.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 69| Part 7| July 2013| Page o1022
https://doi.org/10.1107/S1600536813014670
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