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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Benzyl 2-benzyl-4-[(3aS,7aR)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-isoindol-2-yl]-4-oxo­butano­ate

aCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Hebei Research Center of Pharmaceutical and Chemical Engineering, State Key Laboratory Breeding Base–Hebei Province Key Laboratory of Molecular Chemistry for Drugs, Shijiazhuang 050018, People's Republic of China, bCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China, and cZhongqi Pharmacy (Shijiazhang), Shijiazhuang Pharmaceutical Group Co., Ltd (CSPC) , Shijiazhuang 050051, People's Republic of China
*Correspondence e-mail: zhenhuashang@yahoo.com.cn

(Received 22 August 2012; accepted 31 August 2012; online 5 September 2012)

In the title compound, C26H31NO3, the octa­hydro-1H-isoindole ring is not planar and the two rings are twisted with a C—C—C—C torsion angle of 73.6 (4)°. The six-membered ring has a chair conformation while the five-membered ring has an envelope conformation on the C-atom in position 7a. The H atoms in the 3a- and 7a-psitions are cis and the H—C—C—H torsion angle is 42.36°.

Related literature

The title compound is an inter­mediate of mitiglinide, which was obtained when 2-benzyl-4-[(3aS,7aR)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-isoindol-2-yl]-4-oxobutanoic acid was reacted with 1-(chloro­meth­yl)benzene in ethyl acetate with potassium iodide as catalyst. For the use of mitiglinide, a potassium channel antagonist, in the treatment of type 2 diabetes, see: Reimann et al. (2001[Reimann, F., Prokes, P. & Ashcroft, F. M. (2001). Br. J. Pharmacol. 132, 1542-1548.]).

[Scheme 1]

Experimental

Crystal data
  • C26H31NO3

  • Mr = 405.52

  • Triclinic, P 1

  • a = 5.8542 (12) Å

  • b = 9.0365 (18) Å

  • c = 11.352 (2) Å

  • α = 108.59 (3)°

  • β = 93.94 (3)°

  • γ = 101.23 (3)°

  • V = 552.7 (2) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 294 K

  • 0.16 × 0.14 × 0.10 mm

Data collection
  • Rigaku Saturn70 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.988, Tmax = 0.992

  • 5536 measured reflections

  • 2588 independent reflections

  • 1424 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.106

  • S = 0.89

  • 2588 reflections

  • 271 parameters

  • 3 restraints

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Mitiglinide, a potassium channel antagonist produced by Kissei Pharmaceutical Co., Ltd, was used for the treatment of type 2 diabetes mellitus (Reimann et al., 2001). The title compound, as the key intermediate, was obtained When 2-benzyl-4-((3aS,7aR)-hexahydro -1H-isoindol-2(3H)-yl)-4-oxobutanoic acid was reacted with 1-(chloromethyl)benzene in ethyl acetate with potassium iodide as the catalyst. The octahydro-1H-isoindole ring is not on a plane and the two rings are twisted (C5—C6—C7—C8 = 73.6 (4)°, C3—C2—C1 = 112.5 (3)°, C4—C5—C6 = 111.2 (3)°). The 8-aza bicyclo[4.3.0]nonane ring is almost chair conformation (N1—C1—C2 = 102.8 (2)°, N1—C8—C7 = 105.1 (2)°), The C2 and C7 H atoms are cis form with the H2—C2—C7—H7 torsion angle 42.36°.

Related literature top

The title compound is the key intermediate of mitiglinide, which was obtained when 2-benzyl-4-[(3aS,7aR)-2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl]-4-oxobutanoic acid was reacted with 1-(chloromethyl)benzene in ethyl acetate with potassium iodide as the catalyst. For the use of mitiglinide, a potassium channel antagonist, in the treatment of type 2 diabetes, see: Reimann et al. (2001).

Experimental top

To a solution of 2-benzyl-4-((3aS,7aR)-hexahydro-1H-isoindol-2(3H)-yl) -4-oxobutanoic acid (13.8 g), KI (0.8 g) and potassium carbonate (6.6 g) in ethyl acetate (50 ml), 1-(chloromethyl)benzene (3.7 g) was added droply. After addition, the mixture was heated and reflux for 21 h. The reaction mixture was poured into 60 ml ice-water. The organic layer was seperated and distilled. When the ethyl acetate was recovered, the residue was added 120 ml petroleum ether. The product was obtained through filtration and recystalled. 50 mg of the title compound was dissolved in 50 ml ethanol and the solution was kept at room temperature for 10 d for natural evaporation. Colorless single crystals of the title compound obtained was suitable for X-ray analysis.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), 0.98 Å (tertiary methyl CH group) or 0.97 Å (secondary CH2 group), with Uiso(H)=1.2Ueq(C). The merging of the Friedel pairs are 3840–2588 = 1252.

Structure description top

Mitiglinide, a potassium channel antagonist produced by Kissei Pharmaceutical Co., Ltd, was used for the treatment of type 2 diabetes mellitus (Reimann et al., 2001). The title compound, as the key intermediate, was obtained When 2-benzyl-4-((3aS,7aR)-hexahydro -1H-isoindol-2(3H)-yl)-4-oxobutanoic acid was reacted with 1-(chloromethyl)benzene in ethyl acetate with potassium iodide as the catalyst. The octahydro-1H-isoindole ring is not on a plane and the two rings are twisted (C5—C6—C7—C8 = 73.6 (4)°, C3—C2—C1 = 112.5 (3)°, C4—C5—C6 = 111.2 (3)°). The 8-aza bicyclo[4.3.0]nonane ring is almost chair conformation (N1—C1—C2 = 102.8 (2)°, N1—C8—C7 = 105.1 (2)°), The C2 and C7 H atoms are cis form with the H2—C2—C7—H7 torsion angle 42.36°.

The title compound is the key intermediate of mitiglinide, which was obtained when 2-benzyl-4-[(3aS,7aR)-2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl]-4-oxobutanoic acid was reacted with 1-(chloromethyl)benzene in ethyl acetate with potassium iodide as the catalyst. For the use of mitiglinide, a potassium channel antagonist, in the treatment of type 2 diabetes, see: Reimann et al. (2001).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, drawn with 30% probability ellipsoids.
Benzyl 2-benzyl-4-[(3aS,7aR)-2,3,3a,4,5,6,7,7a- octahydro-1H-isoindol-2-yl]-4-oxobutanoate top
Crystal data top
C26H31NO3Z = 1
Mr = 405.52F(000) = 218
Triclinic, P1Dx = 1.218 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8542 (12) ÅCell parameters from 1681 reflections
b = 9.0365 (18) Åθ = 1.9–27.9°
c = 11.352 (2) ŵ = 0.08 mm1
α = 108.59 (3)°T = 294 K
β = 93.94 (3)°Plate, colorless
γ = 101.23 (3)°0.16 × 0.14 × 0.10 mm
V = 552.7 (2) Å3
Data collection top
Rigaku Saturn70 CCD
diffractometer
2588 independent reflections
Radiation source: rotating anode1424 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.049
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.9°
ω scansh = 77
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1110
Tmin = 0.988, Tmax = 0.992l = 1414
5536 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.0499P)2]
where P = (Fo2 + 2Fc2)/3
2588 reflections(Δ/σ)max = 0.002
271 parametersΔρmax = 0.18 e Å3
3 restraintsΔρmin = 0.20 e Å3
Crystal data top
C26H31NO3γ = 101.23 (3)°
Mr = 405.52V = 552.7 (2) Å3
Triclinic, P1Z = 1
a = 5.8542 (12) ÅMo Kα radiation
b = 9.0365 (18) ŵ = 0.08 mm1
c = 11.352 (2) ÅT = 294 K
α = 108.59 (3)°0.16 × 0.14 × 0.10 mm
β = 93.94 (3)°
Data collection top
Rigaku Saturn70 CCD
diffractometer
2588 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1424 reflections with I > 2σ(I)
Tmin = 0.988, Tmax = 0.992Rint = 0.049
5536 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0433 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 0.89Δρmax = 0.18 e Å3
2588 reflectionsΔρmin = 0.20 e Å3
271 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*/Ueq
O10.1006 (3)0.2391 (3)0.4493 (2)0.0461 (6)
O20.2379 (5)0.2088 (3)0.7354 (3)0.0781 (9)
O30.0275 (4)0.3929 (3)0.7968 (2)0.0530 (6)
N10.1082 (4)0.0726 (3)0.3389 (2)0.0414 (7)
C10.3247 (5)0.0184 (4)0.3070 (3)0.0460 (8)
H1A0.35380.05620.34850.055*
H1B0.45990.10830.33000.055*
C20.2709 (5)0.0637 (4)0.1651 (3)0.0388 (7)
H20.36330.14490.13780.047*
C30.3173 (6)0.0541 (4)0.0949 (3)0.0500 (9)
H3A0.25290.14580.13480.060*
H3B0.48580.09210.10030.060*
C40.2112 (7)0.0190 (5)0.0407 (4)0.0660 (11)
H4A0.27960.10820.08210.079*
H4B0.24580.06020.08190.079*
C50.0515 (7)0.0771 (5)0.0518 (4)0.0683 (12)
H5A0.11790.12320.13980.082*
H5B0.11990.01310.01310.082*
C60.1126 (6)0.2014 (4)0.0109 (3)0.0551 (10)
H6A0.06740.29840.03690.066*
H6B0.28160.22740.01020.066*
C70.0077 (5)0.1453 (4)0.1451 (3)0.0422 (8)
H70.00690.23930.17190.051*
C80.0910 (5)0.0199 (4)0.2404 (3)0.0452 (8)
H8A0.14990.04900.20140.054*
H8B0.21790.07130.27480.054*
C90.0902 (5)0.2018 (4)0.4337 (3)0.0352 (7)
C100.3132 (5)0.3000 (4)0.5201 (3)0.0392 (7)
H10A0.40840.36100.47720.047*
H10B0.40180.22820.53890.047*
C110.2690 (5)0.4157 (4)0.6433 (3)0.0383 (7)
H110.15020.47080.62430.046*
C120.4942 (6)0.5424 (4)0.7134 (3)0.0505 (9)
H12A0.46760.59930.79760.061*
H12B0.62030.48880.72050.061*
C130.5688 (5)0.6615 (4)0.6478 (3)0.0400 (7)
C140.4546 (6)0.7839 (4)0.6598 (3)0.0517 (9)
H140.32650.78780.70400.062*
C150.5261 (7)0.9007 (4)0.6076 (3)0.0639 (11)
H150.44690.98260.61710.077*
C160.7108 (7)0.8964 (5)0.5428 (4)0.0687 (11)
H160.76000.97560.50820.082*
C170.8251 (7)0.7751 (6)0.5284 (4)0.0755 (13)
H170.95160.77150.48310.091*
C180.7548 (6)0.6577 (5)0.5804 (4)0.0589 (10)
H180.83390.57560.56970.071*
C190.1781 (6)0.3255 (4)0.7267 (3)0.0439 (8)
C200.0779 (7)0.3150 (5)0.8789 (3)0.0586 (10)
H20A0.06770.20350.84950.070*
H20B0.24320.31720.87490.070*
C210.0366 (6)0.3918 (4)1.0121 (3)0.0465 (8)
C220.2699 (6)0.4696 (5)1.0456 (4)0.0586 (10)
H220.36250.47870.98380.070*
C230.3670 (8)0.5339 (5)1.1696 (4)0.0681 (11)
H230.52520.58621.19090.082*
C240.2340 (9)0.5220 (5)1.2627 (4)0.0724 (12)
H240.30050.56671.34670.087*
C250.0015 (9)0.4432 (5)1.2297 (4)0.0730 (13)
H250.08980.43151.29150.088*
C260.0973 (7)0.3812 (4)1.1053 (4)0.0564 (9)
H260.25650.33161.08400.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0369 (12)0.0497 (13)0.0454 (14)0.0100 (10)0.0056 (10)0.0075 (11)
O20.122 (2)0.0620 (17)0.083 (2)0.0488 (17)0.0506 (18)0.0457 (16)
O30.0657 (15)0.0563 (15)0.0471 (15)0.0236 (12)0.0191 (12)0.0233 (12)
N10.0273 (13)0.0517 (16)0.0349 (15)0.0075 (12)0.0012 (11)0.0028 (13)
C10.0328 (17)0.056 (2)0.044 (2)0.0137 (14)0.0036 (15)0.0085 (16)
C20.0368 (16)0.0396 (18)0.0369 (18)0.0121 (13)0.0034 (13)0.0070 (14)
C30.0440 (18)0.055 (2)0.055 (2)0.0111 (16)0.0147 (16)0.0213 (18)
C40.088 (3)0.079 (3)0.042 (2)0.028 (2)0.017 (2)0.028 (2)
C50.084 (3)0.079 (3)0.035 (2)0.025 (2)0.0119 (19)0.010 (2)
C60.057 (2)0.048 (2)0.042 (2)0.0109 (17)0.0080 (17)0.0052 (17)
C70.0438 (18)0.0321 (17)0.042 (2)0.0040 (14)0.0001 (15)0.0054 (15)
C80.0309 (16)0.052 (2)0.0377 (19)0.0009 (14)0.0017 (14)0.0019 (15)
C90.0310 (15)0.0403 (17)0.0323 (17)0.0027 (13)0.0034 (12)0.0130 (14)
C100.0348 (16)0.0454 (18)0.0341 (18)0.0055 (13)0.0028 (13)0.0116 (15)
C110.0441 (17)0.0372 (17)0.0297 (17)0.0082 (14)0.0007 (14)0.0082 (14)
C120.062 (2)0.0398 (19)0.042 (2)0.0000 (16)0.0092 (16)0.0134 (16)
C130.0426 (18)0.0352 (17)0.0335 (17)0.0024 (13)0.0067 (14)0.0063 (13)
C140.067 (2)0.046 (2)0.042 (2)0.0200 (18)0.0127 (17)0.0092 (16)
C150.087 (3)0.041 (2)0.062 (3)0.018 (2)0.007 (2)0.015 (2)
C160.079 (3)0.055 (2)0.068 (3)0.003 (2)0.002 (2)0.028 (2)
C170.048 (2)0.097 (4)0.082 (3)0.005 (2)0.017 (2)0.038 (3)
C180.049 (2)0.059 (2)0.070 (3)0.0163 (18)0.0054 (19)0.022 (2)
C190.0541 (19)0.0417 (19)0.0372 (19)0.0149 (16)0.0051 (15)0.0132 (15)
C200.059 (2)0.072 (3)0.052 (2)0.0118 (19)0.0156 (19)0.030 (2)
C210.058 (2)0.044 (2)0.047 (2)0.0195 (17)0.0160 (17)0.0224 (17)
C220.061 (2)0.065 (2)0.053 (2)0.018 (2)0.0123 (19)0.021 (2)
C230.074 (3)0.062 (3)0.067 (3)0.017 (2)0.005 (2)0.021 (2)
C240.114 (4)0.057 (3)0.047 (3)0.030 (3)0.000 (3)0.015 (2)
C250.115 (4)0.059 (3)0.057 (3)0.026 (3)0.038 (3)0.028 (2)
C260.069 (2)0.053 (2)0.055 (2)0.0170 (18)0.023 (2)0.0240 (19)
Geometric parameters (Å, º) top
O1—C91.236 (3)C10—H10B0.9700
O2—C191.204 (4)C11—C191.495 (5)
O3—C191.334 (4)C11—C121.539 (4)
O3—C201.440 (4)C11—H110.9800
N1—C91.340 (4)C12—C131.509 (5)
N1—C81.468 (4)C12—H12A0.9700
N1—C11.473 (4)C12—H12B0.9700
C1—C21.524 (4)C13—C181.373 (5)
C1—H1A0.9700C13—C141.376 (4)
C1—H1B0.9700C14—C151.379 (5)
C2—C31.516 (4)C14—H140.9300
C2—C71.541 (4)C15—C161.348 (5)
C2—H20.9800C15—H150.9300
C3—C41.501 (5)C16—C171.364 (6)
C3—H3A0.9700C16—H160.9300
C3—H3B0.9700C17—C181.381 (6)
C4—C51.507 (6)C17—H170.9300
C4—H4A0.9700C18—H180.9300
C4—H4B0.9700C20—C211.493 (5)
C5—C61.512 (5)C20—H20A0.9700
C5—H5A0.9700C20—H20B0.9700
C5—H5B0.9700C21—C221.374 (5)
C6—C71.515 (5)C21—C261.375 (4)
C6—H6A0.9700C22—C231.372 (5)
C6—H6B0.9700C22—H220.9300
C7—C81.532 (4)C23—C241.374 (6)
C7—H70.9800C23—H230.9300
C8—H8A0.9700C24—C251.372 (7)
C8—H8B0.9700C24—H240.9300
C9—C101.507 (4)C25—C261.379 (6)
C10—C111.529 (4)C25—H250.9300
C10—H10A0.9700C26—H260.9300
C19—O3—C20117.8 (3)C11—C10—H10B108.9
C9—N1—C8121.5 (2)H10A—C10—H10B107.7
C9—N1—C1127.0 (2)C19—C11—C10110.2 (3)
C8—N1—C1110.9 (2)C19—C11—C12109.0 (3)
N1—C1—C2102.8 (2)C10—C11—C12111.7 (3)
N1—C1—H1A111.2C19—C11—H11108.6
C2—C1—H1A111.2C10—C11—H11108.6
N1—C1—H1B111.2C12—C11—H11108.6
C2—C1—H1B111.2C13—C12—C11112.4 (3)
H1A—C1—H1B109.1C13—C12—H12A109.1
C3—C2—C1112.5 (3)C11—C12—H12A109.1
C3—C2—C7111.5 (3)C13—C12—H12B109.1
C1—C2—C7102.8 (3)C11—C12—H12B109.1
C3—C2—H2109.9H12A—C12—H12B107.9
C1—C2—H2109.9C18—C13—C14117.9 (3)
C7—C2—H2109.9C18—C13—C12122.6 (3)
C4—C3—C2112.4 (3)C14—C13—C12119.5 (3)
C4—C3—H3A109.1C13—C14—C15121.3 (3)
C2—C3—H3A109.1C13—C14—H14119.3
C4—C3—H3B109.1C15—C14—H14119.3
C2—C3—H3B109.1C16—C15—C14120.1 (3)
H3A—C3—H3B107.8C16—C15—H15119.9
C3—C4—C5110.2 (3)C14—C15—H15119.9
C3—C4—H4A109.6C15—C16—C17119.7 (4)
C5—C4—H4A109.6C15—C16—H16120.2
C3—C4—H4B109.6C17—C16—H16120.2
C5—C4—H4B109.6C16—C17—C18120.6 (4)
H4A—C4—H4B108.1C16—C17—H17119.7
C4—C5—C6111.2 (3)C18—C17—H17119.7
C4—C5—H5A109.4C13—C18—C17120.4 (3)
C6—C5—H5A109.4C13—C18—H18119.8
C4—C5—H5B109.4C17—C18—H18119.8
C6—C5—H5B109.4O2—C19—O3122.4 (3)
H5A—C5—H5B108.0O2—C19—C11125.2 (3)
C5—C6—C7112.8 (3)O3—C19—C11112.3 (3)
C5—C6—H6A109.0O3—C20—C21112.9 (3)
C7—C6—H6A109.0O3—C20—H20A109.0
C5—C6—H6B109.0C21—C20—H20A109.0
C7—C6—H6B109.0O3—C20—H20B109.0
H6A—C6—H6B107.8C21—C20—H20B109.0
C6—C7—C8115.5 (3)H20A—C20—H20B107.8
C6—C7—C2114.9 (3)C22—C21—C26118.7 (3)
C8—C7—C2102.4 (2)C22—C21—C20123.1 (3)
C6—C7—H7107.8C26—C21—C20118.2 (3)
C8—C7—H7107.8C23—C22—C21120.5 (4)
C2—C7—H7107.8C23—C22—H22119.8
N1—C8—C7105.1 (2)C21—C22—H22119.8
N1—C8—H8A110.7C22—C23—C24120.9 (4)
C7—C8—H8A110.7C22—C23—H23119.5
N1—C8—H8B110.7C24—C23—H23119.5
C7—C8—H8B110.7C25—C24—C23118.9 (4)
H8A—C8—H8B108.8C25—C24—H24120.6
O1—C9—N1121.5 (3)C23—C24—H24120.6
O1—C9—C10121.5 (3)C24—C25—C26120.2 (4)
N1—C9—C10117.0 (2)C24—C25—H25119.9
C9—C10—C11113.3 (2)C26—C25—H25119.9
C9—C10—H10A108.9C21—C26—C25120.8 (4)
C11—C10—H10A108.9C21—C26—H26119.6
C9—C10—H10B108.9C25—C26—H26119.6
C9—N1—C1—C2149.7 (3)C10—C11—C12—C1370.1 (3)
C8—N1—C1—C221.3 (3)C11—C12—C13—C18104.7 (4)
N1—C1—C2—C383.2 (3)C11—C12—C13—C1478.3 (4)
N1—C1—C2—C736.9 (3)C18—C13—C14—C151.0 (5)
C1—C2—C3—C4166.1 (3)C12—C13—C14—C15176.1 (3)
C7—C2—C3—C451.2 (4)C13—C14—C15—C160.3 (5)
C2—C3—C4—C559.6 (4)C14—C15—C16—C170.5 (6)
C3—C4—C5—C659.5 (4)C15—C16—C17—C180.6 (6)
C4—C5—C6—C752.5 (4)C14—C13—C18—C170.9 (5)
C5—C6—C7—C873.6 (4)C12—C13—C18—C17176.1 (4)
C5—C6—C7—C245.4 (4)C16—C17—C18—C130.2 (6)
C3—C2—C7—C644.2 (4)C20—O3—C19—O24.4 (5)
C1—C2—C7—C6165.0 (3)C20—O3—C19—C11178.4 (3)
C3—C2—C7—C881.8 (3)C10—C11—C19—O236.0 (4)
C1—C2—C7—C838.9 (3)C12—C11—C19—O286.9 (4)
C9—N1—C8—C7174.7 (3)C10—C11—C19—O3146.9 (3)
C1—N1—C8—C73.2 (3)C12—C11—C19—O390.2 (3)
C6—C7—C8—N1151.8 (3)C19—O3—C20—C21100.6 (4)
C2—C7—C8—N126.1 (3)O3—C20—C21—C2229.7 (5)
C8—N1—C9—O17.4 (4)O3—C20—C21—C26151.6 (3)
C1—N1—C9—O1177.6 (3)C26—C21—C22—C230.6 (5)
C8—N1—C9—C10172.3 (3)C20—C21—C22—C23178.1 (3)
C1—N1—C9—C102.2 (4)C21—C22—C23—C240.0 (6)
O1—C9—C10—C1115.8 (4)C22—C23—C24—C250.6 (6)
N1—C9—C10—C11164.5 (3)C23—C24—C25—C261.8 (6)
C9—C10—C11—C1973.2 (3)C22—C21—C26—C251.9 (5)
C9—C10—C11—C12165.5 (2)C20—C21—C26—C25176.9 (4)
C19—C11—C12—C13167.8 (3)C24—C25—C26—C212.5 (6)

Experimental details

Crystal data
Chemical formulaC26H31NO3
Mr405.52
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)5.8542 (12), 9.0365 (18), 11.352 (2)
α, β, γ (°)108.59 (3), 93.94 (3), 101.23 (3)
V3)552.7 (2)
Z1
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.16 × 0.14 × 0.10
Data collection
DiffractometerRigaku Saturn70 CCD
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.988, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
5536, 2588, 1424
Rint0.049
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.106, 0.89
No. of reflections2588
No. of parameters271
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.20

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the Natural Science Foundation of Hebei Province (H2012208045), the Scientific and Technological Major Special Project (Major Creation of New Drugs, No. 2011ZX09202–101-22) and the Program for Innovative Research Team of Hebei University of Science and Technology. The authors thank Dr Haibin Song of Nankai University for the data collection and stucture determination.

References

First citationReimann, F., Prokes, P. & Ashcroft, F. M. (2001). Br. J. Pharmacol. 132, 1542–1548.  Web of Science CrossRef PubMed CAS Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds