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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 4| April 2014| Pages o419-o420

(4S,5R)-4-Benz­yl­oxy-5-[4-(cyclo­hexa­ne­carbon­yl)phen­yl]-1-(4-meth­­oxy­benz­yl)pyrrolidin-2-one

aThe Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, People's Republic of China
*Correspondence e-mail: zxiao@xmu.edu.cn

(Received 27 August 2013; accepted 18 February 2014; online 12 March 2014)

The title compound, C32H35NO4, is an unexpected product obtained in the SmI2-mediated radical cross-coupling of a lactam 2-pyridyl sulfone with an arone. The asymmetric unit contains two mol­ecules. In both mol­ecules, the core pyrrolidinone ring adopts an approximate envelope conformation (with the C atom bearling the benzyloxy substituent as the flap) and the cyclo­hexyl ring has a chair conformation. The relative orientation of the two substitutent groups at the 4- and 5-positions of the pyrrolidinone ring is anti in both mol­ecules, with O(benz­yloxy)—C—C—C(benzene) torsion angles of 150.8 (3) and 154.2 (2)°. In the crystal, C—H⋯O inter­actions involving carbonyl groups as acceptors lead to the formation of a tape motif propagating parallel to the a-axis direction.

Related literature

For backround to the synthesis, see: Shiue et al. (1997[Shiue, J.-S., Lin, M.-H. & Fang, J.-M. (1997). J. Org. Chem. 62, 4643-4649.]); Zheng et al. (2005[Zheng, X., Feng, C.-G. & Huang, P.-Q. (2005). Org. Lett. 7, 553-556.]); Hu et al. (2013[Hu, K.-Z., Ma, J., Qiu, S., Zheng, X. & Huang, P.-Q. (2013). J. Org. Chem. 78, 1790-1801.]).

[Scheme 1]

Experimental

Crystal data
  • C32H35NO4

  • Mr = 497.61

  • Monoclinic, P 21

  • a = 9.4964 (4) Å

  • b = 28.6497 (13) Å

  • c = 9.9511 (4) Å

  • β = 96.727 (4)°

  • V = 2688.8 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.2 × 0.12 × 0.09 mm

Data collection
  • Oxford Diffraction SuperNova diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.927, Tmax = 1.000

  • 11184 measured reflections

  • 7540 independent reflections

  • 6140 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.123

  • S = 1.03

  • 7540 reflections

  • 669 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C62—H62⋯O4i 0.93 2.47 3.260 (5) 143
C17—H17⋯O2ii 0.93 2.38 3.237 (4) 153
C49—H49⋯O6ii 0.93 2.33 3.190 (4) 154
Symmetry codes: (i) [-x-1, y-{\script{1\over 2}}, -z-1]; (ii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In the SmI2/HMPA-promoted phenyl-carbonyl coupling reaction, a special type of phenyl radicals were generated from benzaldehyde and acetophenones by Shiue et al. (1997). In addition, using SmI2 as the single electron reductant, acylaminoalkyl radicals were generated from 2-pyridyl sulfides or 2-pyridyl sulfones (Zheng et al., 2005; Hu et al., 2013). So, the SmI2-mediated phenyl-pyrrolidyl coupling of (4S)-1-(4-methoxybenzyl)-4-benzyloxy-5-(pyridin-2-ylsulfonyl)pyrrolidin-2-one with benzoylcyclohexane produced (4S,5R)-4-(benzyloxy)-5-(4-(cyclohexanecarbonyl)phenyl)-1-(4-methoxybenzyl)pyrrolidin-2-one reasonably. Here we report the structure of the title compound.

Related literature top

For backround to the synthesis, see: Shiue et al. (1997); Zheng et al. (2005); Hu et al. (2013).

Experimental top

To a solution of (4S)-1-(4-methoxybenzyl)-4-benzyloxy-5-(pyridin-2-ylsulfonyl)pyrrolidin-2-one (0.5 mmol) and benzoylcyclohexane (1.5 mmol) in dry THF (10 ml) was added a freshly prepared t-BuOH-containing SmI2 (0.1 M in THF, 20 ml, 2.0 mmol) at -60 °C. After being stirred for 2 h, the reaction was quenched with a saturated aqueous solution of NH4Cl (10 ml), and the resulting mixture was extracted with EtOAc (3 × 15 ml). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: EtOAc/Hex = 1: 10) to afford the title compound (white crystals, yield 35%). Single crystals of the tiltle compound were obtained by slow evaporation of a mixture of n-hexane/dichloromethane solution. The title compound was prepared from an optical pure starting material and no racemization was observed in this reaction.

IR (film): 3066, 3027, 2928, 1716, 1611, 1513, 1248, 1316, 1108 cm-1; 1H NMR (400 MHz, CDCl3) δ 1.3–2.0(m,10H), 2.59(dd, J = 3.1, 17.5 Hz,1H), 2.85(dd, J = 6.8, 17.5 Hz,1H), 3.24(m, 1H), 3.49 (d, J = 14.8 Hz, 1H), 3.78(s, 3H), 3.94 (ddd appare. dt, J = 2.4, 3.1, 6.8 Hz, 1H), 4.44 (d, J = 12.1 Hz, 1H), 4.47 (d, J = 12.1 Hz, 1H), 4.49 (d, J = 2.4 Hz, 1H), 5.14 (d, J = 14.8 Hz, 1H), 6.80 (d, J = 8.7 Hz, 2H), 7.02 (d, J = 8.7 Hz, 2H), 7.14–7.20 (m,4H), 7.24–7.31 (m,3H), 7.91–7.96 (m,2H). 13C NMR (100 MHz, CDCl3) δ 25.8 (2 C), 25.9 (2 C), 29.4, 37.2, 43.8, 45.7, 55.3, 67.2, 71.3, 79.2, 114.1, 126.9, 127.6, 128.0, 128.5, 129.2, 129.6, 136.4, 137.2, 142.9, 159.1, 172.9, 203.2. HRESIMS calcd for [C32H35NO4Na]+ (M + Na+): 520.2464; found: 520.2474.

Refinement top

The hydrogen atoms were positioned geometrically, with C—H = 0.93, 0.98, 0.97 and 0.96 Å for phenyl, methine, methylene and methyl H atoms, respectively, and were included in the refinement in the riding model approximation. The displacement parameters of methyl H atoms were set to 1.5 Ueq(C), while those of other H atoms were set to 1.2 Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were merged. The absolute configuration was assigned with reference to the starting materials in the synthetic procedure.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The packed unit cell.
(4S,5R)-4-Benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one top
Crystal data top
C32H35NO4Z = 4
Mr = 497.61F(000) = 1064
Monoclinic, P21Dx = 1.229 Mg m3
a = 9.4964 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 28.6497 (13) ŵ = 0.08 mm1
c = 9.9511 (4) ÅT = 100 K
β = 96.727 (4)°Columnar, colorless
V = 2688.8 (2) Å30.2 × 0.12 × 0.09 mm
Data collection top
Oxford Diffraction SuperNova
diffractometer
7540 independent reflections
Radiation source: fine-focus sealed tube6140 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 10.3415 pixels mm-1θmax = 25.0°, θmin = 3.5°
ω scansh = 119
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2006)
k = 3428
Tmin = 0.927, Tmax = 1.000l = 1111
11184 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.059P)2]
where P = (Fo2 + 2Fc2)/3
7540 reflections(Δ/σ)max < 0.001
669 parametersΔρmax = 0.21 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C32H35NO4V = 2688.8 (2) Å3
Mr = 497.61Z = 4
Monoclinic, P21Mo Kα radiation
a = 9.4964 (4) ŵ = 0.08 mm1
b = 28.6497 (13) ÅT = 100 K
c = 9.9511 (4) Å0.2 × 0.12 × 0.09 mm
β = 96.727 (4)°
Data collection top
Oxford Diffraction SuperNova
diffractometer
7540 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2006)
6140 reflections with I > 2σ(I)
Tmin = 0.927, Tmax = 1.000Rint = 0.037
11184 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0481 restraint
wR(F2) = 0.123H-atom parameters constrained
S = 1.03Δρmax = 0.21 e Å3
7540 reflectionsΔρmin = 0.18 e Å3
669 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 > 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
C10.2734 (5)0.20483 (14)0.1362 (4)0.0441 (10)
H1A0.32360.22010.07030.066*
H1B0.17490.21320.12120.066*
H1C0.28270.17160.12790.066*
C20.3430 (4)0.26598 (12)0.2923 (3)0.0269 (8)
C30.2965 (4)0.30055 (12)0.1985 (3)0.0283 (8)
H30.25140.29250.11360.034*
C40.3183 (3)0.34722 (12)0.2335 (3)0.0252 (8)
H40.28710.37010.17070.030*
C50.3848 (3)0.36064 (11)0.3586 (3)0.0205 (7)
C60.4272 (3)0.32517 (12)0.4524 (3)0.0263 (8)
H60.47100.33310.53780.032*
C70.4050 (4)0.27891 (12)0.4197 (3)0.0294 (9)
H70.43190.25600.48400.035*
C80.4129 (3)0.41149 (11)0.3902 (3)0.0219 (7)
H8A0.50000.42080.35550.026*
H8B0.33630.43000.34440.026*
C90.5492 (3)0.43143 (11)0.6091 (3)0.0251 (8)
C100.5213 (4)0.43434 (14)0.7556 (3)0.0338 (9)
H10A0.51560.46660.78410.041*
H10B0.59590.41880.81410.041*
C110.3807 (4)0.40977 (13)0.7596 (3)0.0283 (8)
H110.32620.42320.82780.034*
C120.3050 (3)0.41663 (12)0.6133 (3)0.0253 (8)
H120.25210.38820.58510.030*
C130.2059 (3)0.45772 (12)0.5976 (3)0.0249 (8)
C140.2547 (4)0.50246 (13)0.5807 (4)0.0435 (10)
H140.35120.50750.57880.052*
C150.1629 (4)0.53984 (13)0.5665 (5)0.0482 (11)
H150.19830.56970.55620.058*
C160.0183 (4)0.53332 (12)0.5676 (3)0.0309 (8)
C170.0315 (3)0.48885 (12)0.5870 (3)0.0237 (8)
H170.12780.48400.59060.028*
C180.0611 (3)0.45149 (12)0.6010 (3)0.0236 (8)
H180.02600.42170.61290.028*
C190.0767 (4)0.57499 (13)0.5449 (4)0.0369 (9)
C200.2344 (3)0.57033 (12)0.5405 (3)0.0309 (8)
H200.25380.54390.59800.037*
C210.3046 (4)0.61276 (17)0.5917 (5)0.0567 (12)
H21A0.27960.63990.54130.068*
H21B0.26930.61770.68610.068*
C220.4661 (4)0.60805 (15)0.5780 (4)0.0438 (10)
H22A0.49230.58350.63740.053*
H22B0.50760.63700.60500.053*
C230.5224 (4)0.59680 (15)0.4343 (4)0.0437 (10)
H23A0.50360.62270.37630.052*
H23B0.62430.59250.42770.052*
C240.4539 (4)0.55266 (19)0.3857 (4)0.0626 (14)
H24A0.49040.54650.29220.075*
H24B0.47740.52620.43980.075*
C250.2919 (4)0.55860 (17)0.3976 (4)0.0489 (11)
H25A0.24880.52990.37050.059*
H25B0.26820.58330.33760.059*
C260.2923 (4)0.33471 (14)0.8139 (4)0.0401 (10)
H26A0.21180.34090.74690.048*
H26B0.26640.34330.90210.048*
C270.3295 (4)0.28346 (14)0.8125 (3)0.0360 (9)
C280.4639 (4)0.26816 (15)0.8651 (4)0.0429 (10)
H280.53260.28950.89930.052*
C290.4947 (5)0.22074 (18)0.8663 (4)0.0578 (12)
H290.58440.21040.90100.069*
C300.3924 (5)0.18886 (17)0.8161 (4)0.0562 (12)
H300.41290.15710.81870.067*
C310.2612 (5)0.20401 (17)0.7627 (4)0.0524 (12)
H310.19290.18260.72740.063*
C320.2299 (5)0.25123 (15)0.7612 (4)0.0436 (10)
H320.14040.26130.72490.052*
C330.7901 (5)0.20396 (14)0.3344 (4)0.0498 (11)
H33A0.85140.21540.39710.075*
H33B0.69540.21500.36020.075*
H33C0.79060.17040.33520.075*
C340.8548 (4)0.26752 (13)0.1822 (3)0.0293 (8)
C350.8183 (4)0.30053 (13)0.2832 (3)0.0295 (8)
H350.78030.29120.36940.035*
C360.8395 (3)0.34752 (12)0.2539 (3)0.0263 (8)
H360.81280.36950.32090.032*
C370.8993 (3)0.36277 (12)0.1273 (3)0.0234 (8)
C380.9335 (3)0.32901 (13)0.0274 (3)0.0276 (8)
H380.97250.33830.05850.033*
C390.9106 (4)0.28211 (13)0.0537 (3)0.0326 (9)
H390.93250.26030.01470.039*
C400.9301 (3)0.41405 (12)0.1030 (3)0.0239 (8)
H40A1.02320.42110.12870.029*
H40B0.86130.43230.16050.029*
C411.0409 (3)0.44337 (11)0.1179 (3)0.0233 (8)
C420.9953 (3)0.45315 (12)0.2555 (3)0.0261 (8)
H42A0.98070.48630.26790.031*
H42B1.06550.44200.32690.031*
C430.8571 (3)0.42648 (11)0.2548 (3)0.0226 (7)
H430.79220.44100.31220.027*
C440.7968 (3)0.42612 (11)0.1026 (3)0.0196 (7)
H440.74860.39640.08080.023*
C450.6947 (3)0.46591 (11)0.0641 (3)0.0201 (7)
C460.7387 (3)0.50796 (12)0.0107 (3)0.0265 (8)
H460.83340.51200.00200.032*
C470.6428 (3)0.54333 (12)0.0232 (3)0.0280 (8)
H470.67380.57100.05900.034*
C480.5013 (3)0.53856 (11)0.0051 (3)0.0227 (7)
C490.4561 (3)0.49667 (11)0.0482 (3)0.0216 (7)
H490.36140.49270.06110.026*
C500.5530 (3)0.46101 (12)0.0819 (3)0.0217 (7)
H500.52200.43330.11710.026*
C510.4028 (4)0.57889 (12)0.0432 (3)0.0281 (8)
C520.2476 (3)0.57508 (12)0.0231 (3)0.0250 (8)
H520.21480.54340.04670.030*
C530.1572 (3)0.60977 (13)0.1126 (3)0.0324 (8)
H53A0.19130.64120.09240.039*
H53B0.16670.60340.20690.039*
C540.0015 (4)0.60658 (13)0.0902 (3)0.0352 (9)
H54A0.05280.62930.14700.042*
H54B0.03440.57580.11600.042*
C550.0171 (4)0.61560 (13)0.0564 (4)0.0340 (8)
H55A0.11600.61150.06940.041*
H55B0.00910.64760.07930.041*
C560.0735 (4)0.58269 (13)0.1495 (3)0.0340 (9)
H56A0.03810.55110.13530.041*
H56B0.06580.59110.24280.041*
C570.2290 (4)0.58421 (13)0.1250 (3)0.0307 (8)
H57A0.28150.56090.18120.037*
H57B0.26800.61460.15120.037*
C580.7806 (4)0.35197 (12)0.3265 (3)0.0276 (8)
H58A0.69960.35740.25950.033*
H58B0.75400.36010.41480.033*
C590.8233 (3)0.30182 (12)0.3248 (3)0.0255 (8)
C600.9602 (4)0.28759 (13)0.3737 (3)0.0298 (8)
H601.02740.30960.40670.036*
C610.9964 (4)0.24096 (13)0.3735 (3)0.0356 (9)
H611.08820.23190.40560.043*
C620.8979 (4)0.20761 (14)0.3260 (3)0.0384 (10)
H620.92280.17620.32750.046*
C630.7621 (4)0.22115 (14)0.2763 (4)0.0380 (9)
H630.69520.19890.24410.046*
C640.7261 (4)0.26768 (13)0.2747 (3)0.0325 (9)
H640.63500.27660.23950.039*
O10.3309 (3)0.21905 (8)0.2685 (2)0.0342 (6)
O20.6627 (2)0.43771 (8)0.5647 (2)0.0298 (6)
O30.4116 (2)0.36182 (9)0.7845 (2)0.0319 (6)
O40.0242 (3)0.61327 (10)0.5212 (3)0.0619 (9)
O50.8393 (3)0.22030 (9)0.2012 (2)0.0390 (6)
O61.1596 (2)0.44863 (8)0.0834 (2)0.0326 (6)
O70.8971 (2)0.38020 (8)0.2972 (2)0.0258 (5)
N10.4250 (2)0.42119 (10)0.5347 (2)0.0215 (6)
N20.9258 (3)0.42805 (10)0.0370 (2)0.0219 (6)
O80.4500 (3)0.61465 (9)0.0869 (3)0.0412 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.064 (3)0.031 (2)0.038 (2)0.011 (2)0.007 (2)0.0052 (17)
C20.0277 (19)0.023 (2)0.0313 (19)0.0009 (15)0.0109 (15)0.0013 (16)
C30.0307 (19)0.032 (2)0.0224 (17)0.0040 (16)0.0043 (14)0.0008 (16)
C40.0244 (18)0.028 (2)0.0238 (17)0.0021 (15)0.0049 (14)0.0022 (15)
C50.0199 (16)0.0258 (19)0.0166 (15)0.0004 (14)0.0062 (13)0.0025 (14)
C60.0282 (19)0.032 (2)0.0186 (16)0.0002 (16)0.0032 (14)0.0003 (15)
C70.033 (2)0.031 (2)0.0252 (18)0.0024 (17)0.0063 (15)0.0082 (16)
C80.0213 (17)0.030 (2)0.0144 (15)0.0006 (14)0.0032 (13)0.0007 (13)
C90.0220 (18)0.025 (2)0.0278 (17)0.0039 (15)0.0017 (15)0.0031 (15)
C100.0294 (19)0.048 (2)0.0234 (17)0.0061 (18)0.0014 (15)0.0053 (17)
C110.0260 (18)0.040 (2)0.0195 (17)0.0036 (16)0.0062 (14)0.0041 (15)
C120.0205 (17)0.032 (2)0.0245 (17)0.0038 (15)0.0076 (14)0.0041 (15)
C130.0233 (18)0.032 (2)0.0201 (16)0.0046 (15)0.0044 (13)0.0098 (15)
C140.021 (2)0.035 (2)0.077 (3)0.0073 (18)0.0156 (19)0.011 (2)
C150.033 (2)0.024 (2)0.091 (3)0.0079 (18)0.019 (2)0.009 (2)
C160.030 (2)0.027 (2)0.0366 (19)0.0041 (16)0.0077 (16)0.0095 (16)
C170.0194 (17)0.032 (2)0.0195 (16)0.0028 (16)0.0030 (13)0.0028 (15)
C180.0247 (18)0.031 (2)0.0160 (15)0.0066 (16)0.0035 (13)0.0018 (14)
C190.038 (2)0.025 (2)0.048 (2)0.0058 (18)0.0065 (18)0.0083 (18)
C200.0284 (19)0.025 (2)0.0386 (19)0.0005 (15)0.0017 (16)0.0051 (16)
C210.045 (2)0.055 (3)0.069 (3)0.002 (2)0.002 (2)0.035 (2)
C220.043 (2)0.044 (3)0.046 (2)0.004 (2)0.0114 (18)0.014 (2)
C230.037 (2)0.060 (3)0.034 (2)0.014 (2)0.0033 (17)0.0076 (19)
C240.047 (3)0.100 (4)0.038 (2)0.017 (3)0.005 (2)0.026 (2)
C250.044 (2)0.069 (3)0.033 (2)0.019 (2)0.0019 (18)0.009 (2)
C260.033 (2)0.053 (3)0.037 (2)0.0020 (19)0.0148 (17)0.0120 (19)
C270.038 (2)0.047 (2)0.0262 (18)0.002 (2)0.0161 (16)0.0091 (17)
C280.033 (2)0.045 (3)0.054 (2)0.0050 (19)0.0184 (19)0.008 (2)
C290.050 (3)0.070 (4)0.059 (3)0.013 (3)0.027 (2)0.007 (3)
C300.071 (3)0.049 (3)0.054 (3)0.006 (3)0.032 (2)0.006 (2)
C310.064 (3)0.055 (3)0.041 (2)0.015 (2)0.020 (2)0.006 (2)
C320.046 (3)0.054 (3)0.033 (2)0.000 (2)0.0133 (18)0.0033 (19)
C330.077 (3)0.036 (2)0.039 (2)0.006 (2)0.013 (2)0.0042 (19)
C340.032 (2)0.027 (2)0.0318 (19)0.0035 (16)0.0149 (16)0.0018 (16)
C350.033 (2)0.036 (2)0.0206 (17)0.0036 (17)0.0075 (15)0.0034 (16)
C360.0263 (18)0.036 (2)0.0178 (16)0.0048 (16)0.0067 (14)0.0059 (16)
C370.0210 (17)0.031 (2)0.0194 (16)0.0019 (15)0.0079 (14)0.0018 (14)
C380.0272 (19)0.037 (2)0.0189 (17)0.0048 (16)0.0053 (14)0.0001 (16)
C390.036 (2)0.037 (2)0.0251 (18)0.0073 (18)0.0050 (16)0.0050 (16)
C400.0237 (17)0.033 (2)0.0163 (15)0.0026 (15)0.0064 (13)0.0037 (14)
C410.0233 (19)0.0219 (18)0.0241 (17)0.0001 (15)0.0002 (15)0.0101 (14)
C420.0272 (18)0.030 (2)0.0213 (16)0.0034 (16)0.0011 (14)0.0006 (14)
C430.0299 (18)0.0212 (19)0.0173 (15)0.0028 (15)0.0051 (13)0.0012 (14)
C440.0189 (16)0.0198 (18)0.0212 (16)0.0012 (14)0.0072 (13)0.0018 (14)
C450.0196 (17)0.0259 (19)0.0151 (14)0.0031 (14)0.0038 (13)0.0055 (14)
C460.0193 (18)0.028 (2)0.0315 (18)0.0035 (15)0.0003 (14)0.0010 (15)
C470.0296 (19)0.027 (2)0.0275 (17)0.0059 (16)0.0042 (15)0.0019 (15)
C480.0239 (18)0.0206 (18)0.0234 (16)0.0007 (14)0.0024 (13)0.0003 (14)
C490.0207 (17)0.027 (2)0.0173 (15)0.0005 (15)0.0040 (13)0.0028 (14)
C500.0230 (18)0.0272 (19)0.0156 (15)0.0046 (15)0.0052 (13)0.0013 (14)
C510.034 (2)0.024 (2)0.0268 (18)0.0029 (17)0.0055 (15)0.0021 (15)
C520.0243 (18)0.0178 (18)0.0325 (18)0.0011 (15)0.0019 (15)0.0008 (15)
C530.0332 (19)0.032 (2)0.0314 (18)0.0024 (17)0.0019 (16)0.0038 (16)
C540.032 (2)0.027 (2)0.044 (2)0.0041 (17)0.0043 (17)0.0009 (18)
C550.0286 (19)0.024 (2)0.051 (2)0.0002 (16)0.0080 (16)0.0042 (17)
C560.032 (2)0.037 (2)0.0346 (19)0.0016 (17)0.0099 (16)0.0052 (16)
C570.0285 (19)0.036 (2)0.0274 (18)0.0003 (16)0.0006 (15)0.0007 (15)
C580.0299 (19)0.029 (2)0.0253 (17)0.0004 (16)0.0100 (15)0.0035 (15)
C590.0286 (18)0.030 (2)0.0195 (16)0.0001 (16)0.0108 (14)0.0044 (15)
C600.035 (2)0.028 (2)0.0286 (18)0.0009 (17)0.0104 (15)0.0003 (16)
C610.032 (2)0.040 (2)0.036 (2)0.0064 (18)0.0103 (16)0.0043 (17)
C620.050 (3)0.030 (2)0.037 (2)0.0064 (19)0.0125 (19)0.0038 (17)
C630.041 (2)0.034 (2)0.041 (2)0.0049 (19)0.0116 (18)0.0035 (18)
C640.030 (2)0.038 (2)0.0308 (19)0.0014 (18)0.0096 (16)0.0017 (17)
O10.0473 (16)0.0222 (14)0.0343 (13)0.0019 (11)0.0095 (11)0.0026 (11)
O20.0232 (13)0.0340 (15)0.0327 (13)0.0076 (11)0.0062 (10)0.0014 (11)
O30.0292 (13)0.0431 (17)0.0244 (12)0.0000 (12)0.0070 (10)0.0093 (11)
O40.0408 (17)0.0285 (17)0.117 (3)0.0060 (14)0.0120 (16)0.0074 (17)
O50.0519 (17)0.0327 (16)0.0340 (13)0.0044 (13)0.0111 (12)0.0021 (12)
O60.0226 (13)0.0391 (15)0.0368 (14)0.0047 (11)0.0069 (11)0.0110 (11)
O70.0250 (12)0.0279 (14)0.0254 (12)0.0007 (10)0.0067 (10)0.0067 (10)
N10.0167 (13)0.0323 (16)0.0162 (12)0.0066 (12)0.0052 (11)0.0039 (12)
N20.0184 (14)0.0318 (17)0.0163 (12)0.0017 (12)0.0049 (11)0.0012 (12)
O80.0370 (15)0.0243 (15)0.0645 (17)0.0000 (12)0.0147 (12)0.0103 (13)
Geometric parameters (Å, º) top
C1—O11.425 (4)C33—O51.432 (4)
C1—H1A0.9600C33—H33A0.9600
C1—H1B0.9600C33—H33B0.9600
C1—H1C0.9600C33—H33C0.9600
C2—O11.368 (4)C34—O51.372 (4)
C2—C71.385 (5)C34—C391.390 (5)
C2—C31.397 (5)C34—C351.394 (5)
C3—C41.391 (5)C35—C361.387 (5)
C3—H30.9300C35—H350.9300
C4—C51.383 (4)C36—C371.390 (4)
C4—H40.9300C36—H360.9300
C5—C61.406 (5)C37—C381.398 (5)
C5—C81.508 (5)C37—C401.512 (5)
C6—C71.375 (5)C38—C391.381 (5)
C6—H60.9300C38—H380.9300
C7—H70.9300C39—H390.9300
C8—N11.456 (4)C40—N21.455 (4)
C8—H8A0.9700C40—H40A0.9700
C8—H8B0.9700C40—H40B0.9700
C9—O21.226 (4)C41—O61.224 (4)
C9—N11.349 (4)C41—N21.352 (4)
C9—C101.514 (4)C41—C421.511 (4)
C10—C111.514 (5)C42—C431.518 (4)
C10—H10A0.9700C42—H42A0.9700
C10—H10B0.9700C42—H42B0.9700
C11—O31.420 (4)C43—O71.429 (4)
C11—C121.559 (4)C43—C441.556 (4)
C11—H110.9800C43—H430.9800
C12—N11.461 (4)C44—N21.455 (4)
C12—C131.504 (5)C44—C451.517 (4)
C12—H120.9800C44—H440.9800
C13—C141.380 (5)C45—C501.385 (4)
C13—C181.390 (5)C45—C461.400 (5)
C14—C151.377 (5)C46—C471.378 (5)
C14—H140.9300C46—H460.9300
C15—C161.388 (5)C47—C481.383 (4)
C15—H150.9300C47—H470.9300
C16—C171.380 (5)C48—C491.400 (5)
C16—C191.497 (5)C48—C511.507 (5)
C17—C181.382 (5)C49—C501.389 (5)
C17—H170.9300C49—H490.9300
C18—H180.9300C50—H500.9300
C19—O41.239 (5)C51—O81.219 (4)
C19—C201.499 (5)C51—C521.515 (5)
C20—C251.500 (5)C52—C571.526 (5)
C20—C211.504 (5)C52—C531.529 (4)
C20—H200.9800C52—H520.9800
C21—C221.529 (5)C53—C541.524 (5)
C21—H21A0.9700C53—H53A0.9700
C21—H21B0.9700C53—H53B0.9700
C22—C231.502 (5)C54—C551.513 (5)
C22—H22A0.9700C54—H54A0.9700
C22—H22B0.9700C54—H54B0.9700
C23—C241.526 (6)C55—C561.517 (5)
C23—H23A0.9700C55—H55A0.9700
C23—H23B0.9700C55—H55B0.9700
C24—C251.539 (6)C56—C571.525 (5)
C24—H24A0.9700C56—H56A0.9700
C24—H24B0.9700C56—H56B0.9700
C25—H25A0.9700C57—H57A0.9700
C25—H25B0.9700C57—H57B0.9700
C26—O31.432 (4)C58—O71.428 (4)
C26—C271.511 (6)C58—C591.494 (5)
C26—H26A0.9700C58—H58A0.9700
C26—H26B0.9700C58—H58B0.9700
C27—C321.376 (5)C59—C601.395 (5)
C27—C281.392 (5)C59—C641.396 (5)
C28—C291.389 (6)C60—C611.379 (5)
C28—H280.9300C60—H600.9300
C29—C301.383 (6)C61—C621.381 (5)
C29—H290.9300C61—H610.9300
C30—C311.367 (6)C62—C631.382 (5)
C30—H300.9300C62—H620.9300
C31—C321.385 (6)C63—C641.376 (5)
C31—H310.9300C63—H630.9300
C32—H320.9300C64—H640.9300
O1—C1—H1A109.5H33B—C33—H33C109.5
O1—C1—H1B109.5O5—C34—C39116.5 (3)
H1A—C1—H1B109.5O5—C34—C35123.8 (3)
O1—C1—H1C109.5C39—C34—C35119.7 (3)
H1A—C1—H1C109.5C36—C35—C34119.3 (3)
H1B—C1—H1C109.5C36—C35—H35120.4
O1—C2—C7116.1 (3)C34—C35—H35120.4
O1—C2—C3124.6 (3)C35—C36—C37122.0 (3)
C7—C2—C3119.3 (3)C35—C36—H36119.0
C4—C3—C2119.2 (3)C37—C36—H36119.0
C4—C3—H3120.4C36—C37—C38117.6 (3)
C2—C3—H3120.4C36—C37—C40120.1 (3)
C5—C4—C3122.1 (3)C38—C37—C40122.3 (3)
C5—C4—H4118.9C39—C38—C37121.3 (3)
C3—C4—H4118.9C39—C38—H38119.3
C4—C5—C6117.5 (3)C37—C38—H38119.3
C4—C5—C8120.5 (3)C38—C39—C34120.1 (3)
C6—C5—C8122.0 (3)C38—C39—H39120.0
C7—C6—C5121.0 (3)C34—C39—H39120.0
C7—C6—H6119.5N2—C40—C37113.2 (3)
C5—C6—H6119.5N2—C40—H40A108.9
C6—C7—C2120.7 (3)C37—C40—H40A108.9
C6—C7—H7119.6N2—C40—H40B108.9
C2—C7—H7119.6C37—C40—H40B108.9
N1—C8—C5112.4 (3)H40A—C40—H40B107.7
N1—C8—H8A109.1O6—C41—N2125.4 (3)
C5—C8—H8A109.1O6—C41—C42127.0 (3)
N1—C8—H8B109.1N2—C41—C42107.6 (3)
C5—C8—H8B109.1C41—C42—C43104.0 (2)
H8A—C8—H8B107.8C41—C42—H42A111.0
O2—C9—N1125.7 (3)C43—C42—H42A111.0
O2—C9—C10126.9 (3)C41—C42—H42B111.0
N1—C9—C10107.5 (3)C43—C42—H42B111.0
C9—C10—C11104.7 (3)H42A—C42—H42B109.0
C9—C10—H10A110.8O7—C43—C42105.4 (2)
C11—C10—H10A110.8O7—C43—C44109.6 (2)
C9—C10—H10B110.8C42—C43—C44103.1 (2)
C11—C10—H10B110.8O7—C43—H43112.7
H10A—C10—H10B108.9C42—C43—H43112.7
O3—C11—C10106.8 (3)C44—C43—H43112.7
O3—C11—C12110.4 (3)N2—C44—C45113.9 (3)
C10—C11—C12103.2 (3)N2—C44—C43101.7 (2)
O3—C11—H11112.0C45—C44—C43113.1 (2)
C10—C11—H11112.0N2—C44—H44109.3
C12—C11—H11112.0C45—C44—H44109.3
N1—C12—C13113.1 (3)C43—C44—H44109.3
N1—C12—C11102.0 (2)C50—C45—C46118.3 (3)
C13—C12—C11114.2 (3)C50—C45—C44119.6 (3)
N1—C12—H12109.1C46—C45—C44122.1 (3)
C13—C12—H12109.1C47—C46—C45120.5 (3)
C11—C12—H12109.1C47—C46—H46119.8
C14—C13—C18118.0 (3)C45—C46—H46119.8
C14—C13—C12121.7 (3)C46—C47—C48121.3 (3)
C18—C13—C12120.4 (3)C46—C47—H47119.3
C15—C14—C13121.2 (3)C48—C47—H47119.3
C15—C14—H14119.4C47—C48—C49118.7 (3)
C13—C14—H14119.4C47—C48—C51118.4 (3)
C14—C15—C16120.6 (4)C49—C48—C51122.9 (3)
C14—C15—H15119.7C50—C49—C48119.8 (3)
C16—C15—H15119.7C50—C49—H49120.1
C17—C16—C15118.7 (3)C48—C49—H49120.1
C17—C16—C19123.2 (3)C45—C50—C49121.4 (3)
C15—C16—C19118.1 (3)C45—C50—H50119.3
C16—C17—C18120.3 (3)C49—C50—H50119.3
C16—C17—H17119.9O8—C51—C48119.4 (3)
C18—C17—H17119.9O8—C51—C52120.8 (3)
C17—C18—C13121.2 (3)C48—C51—C52119.8 (3)
C17—C18—H18119.4C51—C52—C57109.9 (2)
C13—C18—H18119.4C51—C52—C53111.4 (3)
O4—C19—C16119.1 (3)C57—C52—C53109.3 (3)
O4—C19—C20119.7 (3)C51—C52—H52108.8
C16—C19—C20121.0 (3)C57—C52—H52108.8
C19—C20—C25107.4 (3)C53—C52—H52108.8
C19—C20—C21113.5 (3)C54—C53—C52111.3 (3)
C25—C20—C21112.1 (3)C54—C53—H53A109.4
C19—C20—H20107.9C52—C53—H53A109.4
C25—C20—H20107.9C54—C53—H53B109.4
C21—C20—H20107.9C52—C53—H53B109.4
C20—C21—C22112.2 (3)H53A—C53—H53B108.0
C20—C21—H21A109.2C55—C54—C53110.9 (3)
C22—C21—H21A109.2C55—C54—H54A109.5
C20—C21—H21B109.2C53—C54—H54A109.5
C22—C21—H21B109.2C55—C54—H54B109.5
H21A—C21—H21B107.9C53—C54—H54B109.5
C23—C22—C21110.2 (3)H54A—C54—H54B108.1
C23—C22—H22A109.6C54—C55—C56111.1 (3)
C21—C22—H22A109.6C54—C55—H55A109.4
C23—C22—H22B109.6C56—C55—H55A109.4
C21—C22—H22B109.6C54—C55—H55B109.4
H22A—C22—H22B108.1C56—C55—H55B109.4
C22—C23—C24111.2 (3)H55A—C55—H55B108.0
C22—C23—H23A109.4C55—C56—C57112.0 (3)
C24—C23—H23A109.4C55—C56—H56A109.2
C22—C23—H23B109.4C57—C56—H56A109.2
C24—C23—H23B109.4C55—C56—H56B109.2
H23A—C23—H23B108.0C57—C56—H56B109.2
C23—C24—C25110.1 (4)H56A—C56—H56B107.9
C23—C24—H24A109.6C56—C57—C52111.9 (3)
C25—C24—H24A109.6C56—C57—H57A109.2
C23—C24—H24B109.6C52—C57—H57A109.2
C25—C24—H24B109.6C56—C57—H57B109.2
H24A—C24—H24B108.2C52—C57—H57B109.2
C20—C25—C24110.3 (3)H57A—C57—H57B107.9
C20—C25—H25A109.6O7—C58—C59108.9 (3)
C24—C25—H25A109.6O7—C58—H58A109.9
C20—C25—H25B109.6C59—C58—H58A109.9
C24—C25—H25B109.6O7—C58—H58B109.9
H25A—C25—H25B108.1C59—C58—H58B109.9
O3—C26—C27109.5 (3)H58A—C58—H58B108.3
O3—C26—H26A109.8C60—C59—C64118.0 (3)
C27—C26—H26A109.8C60—C59—C58121.4 (3)
O3—C26—H26B109.8C64—C59—C58120.6 (3)
C27—C26—H26B109.8C61—C60—C59120.3 (3)
H26A—C26—H26B108.2C61—C60—H60119.8
C32—C27—C28119.2 (4)C59—C60—H60119.8
C32—C27—C26120.3 (3)C60—C61—C62120.8 (3)
C28—C27—C26120.5 (4)C60—C61—H61119.6
C29—C28—C27119.6 (4)C62—C61—H61119.6
C29—C28—H28120.2C61—C62—C63119.6 (4)
C27—C28—H28120.2C61—C62—H62120.2
C30—C29—C28120.3 (4)C63—C62—H62120.2
C30—C29—H29119.9C64—C63—C62119.8 (4)
C28—C29—H29119.9C64—C63—H63120.1
C31—C30—C29120.0 (5)C62—C63—H63120.1
C31—C30—H30120.0C63—C64—C59121.5 (3)
C29—C30—H30120.0C63—C64—H64119.3
C30—C31—C32119.9 (4)C59—C64—H64119.3
C30—C31—H31120.0C2—O1—C1117.1 (3)
C32—C31—H31120.0C11—O3—C26114.1 (3)
C27—C32—C31121.0 (4)C34—O5—C33117.9 (3)
C27—C32—H32119.5C58—O7—C43113.6 (2)
C31—C32—H32119.5C9—N1—C8123.1 (3)
O5—C33—H33A109.5C9—N1—C12114.3 (2)
O5—C33—H33B109.5C8—N1—C12122.3 (2)
H33A—C33—H33B109.5C41—N2—C44114.2 (2)
O5—C33—H33C109.5C41—N2—C40123.2 (3)
H33A—C33—H33C109.5C44—N2—C40122.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C62—H62···O4i0.932.473.260 (5)143
C17—H17···O2ii0.932.383.237 (4)153
C49—H49···O6ii0.932.333.190 (4)154
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C62—H62···O4i0.932.473.260 (5)142.7
C17—H17···O2ii0.932.383.237 (4)153.2
C49—H49···O6ii0.932.333.190 (4)154.1
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x1, y, z.
 

Acknowledgements

The authors acknowledge project sponsorship by SRF for ROCS, SEM.

References

First citationHu, K.-Z., Ma, J., Qiu, S., Zheng, X. & Huang, P.-Q. (2013). J. Org. Chem. 78, 1790–1801.  Web of Science CrossRef CAS PubMed Google Scholar
First citationOxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShiue, J.-S., Lin, M.-H. & Fang, J.-M. (1997). J. Org. Chem. 62, 4643–4649.  CrossRef CAS Web of Science Google Scholar
First citationZheng, X., Feng, C.-G. & Huang, P.-Q. (2005). Org. Lett. 7, 553–556.  Web of Science CrossRef PubMed CAS 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
Volume 70| Part 4| April 2014| Pages o419-o420
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds