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

Gao, Y.-J.; Ma, J.; Zheng, X.

doi:10.1107/S1600536814003638

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages o419-o420

doi:10.1107/S1600536814003638

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

Yan-Jiao Gao,^a Jie Ma ^a and Xiao Zheng ^a ^*

^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.

CCDC reference: 987472

Related literature

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

Experimental

Crystal data

C₃₂H₃₅NO₄
M_r = 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 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.927, T_max = 1.000
11184 measured reflections
7540 independent reflections
6140 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 987472

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814003638/fy2104sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003638/fy2104Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814003638/fy2104Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536814003638/fy2104Isup4.cml

checkCIF report

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.

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

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids.
	Fig. 2. The packed unit cell.

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

Crystal data top

C₃₂H₃₅NO₄	Z = 4
M_r = 497.61	F(000) = 1064
Monoclinic, P2₁	D_x = 1.229 Mg m⁻³
a = 9.4964 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 28.6497 (13) Å	µ = 0.08 mm⁻¹
c = 9.9511 (4) Å	T = 100 K
β = 96.727 (4)°	Columnar, colorless
V = 2688.8 (2) Å³	0.2 × 0.12 × 0.09 mm

Data collection top

Oxford Diffraction SuperNova diffractometer	7540 independent reflections
Radiation source: fine-focus sealed tube	6140 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 10.3415 pixels mm^-1	θ_max = 25.0°, θ_min = 3.5°
ω scans	h = −11→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −34→28
T_min = 0.927, T_max = 1.000	l = −11→11
11184 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.059P)²] where P = (F_o² + 2F_c²)/3
7540 reflections	(Δ/σ)_max < 0.001
669 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₃₂H₃₅NO₄	V = 2688.8 (2) Å³
M_r = 497.61	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 9.4964 (4) Å	µ = 0.08 mm⁻¹
b = 28.6497 (13) Å	T = 100 K
c = 9.9511 (4) Å	0.2 × 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)
T_min = 0.927, T_max = 1.000	R_int = 0.037
11184 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.123	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
7540 reflections	Δρ_min = −0.18 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.2734 (5)	0.20483 (14)	0.1362 (4)	0.0441 (10)
H1A	0.3236	0.2201	0.0703	0.066*
H1B	0.1749	0.2132	0.1212	0.066*
H1C	0.2827	0.1716	0.1279	0.066*
C2	0.3430 (4)	0.26598 (12)	0.2923 (3)	0.0269 (8)
C3	0.2965 (4)	0.30055 (12)	0.1985 (3)	0.0283 (8)
H3	0.2514	0.2925	0.1136	0.034*
C4	0.3183 (3)	0.34722 (12)	0.2335 (3)	0.0252 (8)
H4	0.2871	0.3701	0.1707	0.030*
C5	0.3848 (3)	0.36064 (11)	0.3586 (3)	0.0205 (7)
C6	0.4272 (3)	0.32517 (12)	0.4524 (3)	0.0263 (8)
H6	0.4710	0.3331	0.5378	0.032*
C7	0.4050 (4)	0.27891 (12)	0.4197 (3)	0.0294 (9)
H7	0.4319	0.2560	0.4840	0.035*
C8	0.4129 (3)	0.41149 (11)	0.3902 (3)	0.0219 (7)
H8A	0.5000	0.4208	0.3555	0.026*
H8B	0.3363	0.4300	0.3444	0.026*
C9	0.5492 (3)	0.43143 (11)	0.6091 (3)	0.0251 (8)
C10	0.5213 (4)	0.43434 (14)	0.7556 (3)	0.0338 (9)
H10A	0.5156	0.4666	0.7841	0.041*
H10B	0.5959	0.4188	0.8141	0.041*
C11	0.3807 (4)	0.40977 (13)	0.7596 (3)	0.0283 (8)
H11	0.3262	0.4232	0.8278	0.034*
C12	0.3050 (3)	0.41663 (12)	0.6133 (3)	0.0253 (8)
H12	0.2521	0.3882	0.5851	0.030*
C13	0.2059 (3)	0.45772 (12)	0.5976 (3)	0.0249 (8)
C14	0.2547 (4)	0.50246 (13)	0.5807 (4)	0.0435 (10)
H14	0.3512	0.5075	0.5788	0.052*
C15	0.1629 (4)	0.53984 (13)	0.5665 (5)	0.0482 (11)
H15	0.1983	0.5697	0.5562	0.058*
C16	0.0183 (4)	0.53332 (12)	0.5676 (3)	0.0309 (8)
C17	−0.0315 (3)	0.48885 (12)	0.5870 (3)	0.0237 (8)
H17	−0.1278	0.4840	0.5906	0.028*
C18	0.0611 (3)	0.45149 (12)	0.6010 (3)	0.0236 (8)
H18	0.0260	0.4217	0.6129	0.028*
C19	−0.0767 (4)	0.57499 (13)	0.5449 (4)	0.0369 (9)
C20	−0.2344 (3)	0.57033 (12)	0.5405 (3)	0.0309 (8)
H20	−0.2538	0.5439	0.5980	0.037*
C21	−0.3046 (4)	0.61276 (17)	0.5917 (5)	0.0567 (12)
H21A	−0.2796	0.6399	0.5413	0.068*
H21B	−0.2693	0.6177	0.6861	0.068*
C22	−0.4661 (4)	0.60805 (15)	0.5780 (4)	0.0438 (10)
H22A	−0.4923	0.5835	0.6374	0.053*
H22B	−0.5076	0.6370	0.6050	0.053*
C23	−0.5224 (4)	0.59680 (15)	0.4343 (4)	0.0437 (10)
H23A	−0.5036	0.6227	0.3763	0.052*
H23B	−0.6243	0.5925	0.4277	0.052*
C24	−0.4539 (4)	0.55266 (19)	0.3857 (4)	0.0626 (14)
H24A	−0.4904	0.5465	0.2922	0.075*
H24B	−0.4774	0.5262	0.4398	0.075*
C25	−0.2919 (4)	0.55860 (17)	0.3976 (4)	0.0489 (11)
H25A	−0.2488	0.5299	0.3705	0.059*
H25B	−0.2682	0.5833	0.3376	0.059*
C26	0.2923 (4)	0.33471 (14)	0.8139 (4)	0.0401 (10)
H26A	0.2118	0.3409	0.7469	0.048*
H26B	0.2664	0.3433	0.9021	0.048*
C27	0.3295 (4)	0.28346 (14)	0.8125 (3)	0.0360 (9)
C28	0.4639 (4)	0.26816 (15)	0.8651 (4)	0.0429 (10)
H28	0.5326	0.2895	0.8993	0.052*
C29	0.4947 (5)	0.22074 (18)	0.8663 (4)	0.0578 (12)
H29	0.5844	0.2104	0.9010	0.069*
C30	0.3924 (5)	0.18886 (17)	0.8161 (4)	0.0562 (12)
H30	0.4129	0.1571	0.8187	0.067*
C31	0.2612 (5)	0.20401 (17)	0.7627 (4)	0.0524 (12)
H31	0.1929	0.1826	0.7274	0.063*
C32	0.2299 (5)	0.25123 (15)	0.7612 (4)	0.0436 (10)
H32	0.1404	0.2613	0.7249	0.052*
C33	0.7901 (5)	0.20396 (14)	−0.3344 (4)	0.0498 (11)
H33A	0.8514	0.2154	−0.3971	0.075*
H33B	0.6954	0.2150	−0.3602	0.075*
H33C	0.7906	0.1704	−0.3352	0.075*
C34	0.8548 (4)	0.26752 (13)	−0.1822 (3)	0.0293 (8)
C35	0.8183 (4)	0.30053 (13)	−0.2832 (3)	0.0295 (8)
H35	0.7803	0.2912	−0.3694	0.035*
C36	0.8395 (3)	0.34752 (12)	−0.2539 (3)	0.0263 (8)
H36	0.8128	0.3695	−0.3209	0.032*
C37	0.8993 (3)	0.36277 (12)	−0.1273 (3)	0.0234 (8)
C38	0.9335 (3)	0.32901 (13)	−0.0274 (3)	0.0276 (8)
H38	0.9725	0.3383	0.0585	0.033*
C39	0.9106 (4)	0.28211 (13)	−0.0537 (3)	0.0326 (9)
H39	0.9325	0.2603	0.0147	0.039*
C40	0.9301 (3)	0.41405 (12)	−0.1030 (3)	0.0239 (8)
H40A	1.0232	0.4211	−0.1287	0.029*
H40B	0.8613	0.4323	−0.1605	0.029*
C41	1.0409 (3)	0.44337 (11)	0.1179 (3)	0.0233 (8)
C42	0.9953 (3)	0.45315 (12)	0.2555 (3)	0.0261 (8)
H42A	0.9807	0.4863	0.2679	0.031*
H42B	1.0655	0.4420	0.3269	0.031*
C43	0.8571 (3)	0.42648 (11)	0.2548 (3)	0.0226 (7)
H43	0.7922	0.4410	0.3122	0.027*
C44	0.7968 (3)	0.42612 (11)	0.1026 (3)	0.0196 (7)
H44	0.7486	0.3964	0.0808	0.023*
C45	0.6947 (3)	0.46591 (11)	0.0641 (3)	0.0201 (7)
C46	0.7387 (3)	0.50796 (12)	0.0107 (3)	0.0265 (8)
H46	0.8334	0.5120	−0.0020	0.032*
C47	0.6428 (3)	0.54333 (12)	−0.0232 (3)	0.0280 (8)
H47	0.6738	0.5710	−0.0590	0.034*
C48	0.5013 (3)	0.53856 (11)	−0.0051 (3)	0.0227 (7)
C49	0.4561 (3)	0.49667 (11)	0.0482 (3)	0.0216 (7)
H49	0.3614	0.4927	0.0611	0.026*
C50	0.5530 (3)	0.46101 (12)	0.0819 (3)	0.0217 (7)
H50	0.5220	0.4333	0.1171	0.026*
C51	0.4028 (4)	0.57889 (12)	−0.0432 (3)	0.0281 (8)
C52	0.2476 (3)	0.57508 (12)	−0.0231 (3)	0.0250 (8)
H52	0.2148	0.5434	−0.0467	0.030*
C53	0.1572 (3)	0.60977 (13)	−0.1126 (3)	0.0324 (8)
H53A	0.1913	0.6412	−0.0924	0.039*
H53B	0.1667	0.6034	−0.2069	0.039*
C54	0.0015 (4)	0.60658 (13)	−0.0902 (3)	0.0352 (9)
H54A	−0.0528	0.6293	−0.1470	0.042*
H54B	−0.0344	0.5758	−0.1160	0.042*
C55	−0.0171 (4)	0.61560 (13)	0.0564 (4)	0.0340 (8)
H55A	−0.1160	0.6115	0.0694	0.041*
H55B	0.0091	0.6476	0.0793	0.041*
C56	0.0735 (4)	0.58269 (13)	0.1495 (3)	0.0340 (9)
H56A	0.0381	0.5511	0.1353	0.041*
H56B	0.0658	0.5911	0.2428	0.041*
C57	0.2290 (4)	0.58421 (13)	0.1250 (3)	0.0307 (8)
H57A	0.2815	0.5609	0.1812	0.037*
H57B	0.2680	0.6146	0.1512	0.037*
C58	0.7806 (4)	0.35197 (12)	0.3265 (3)	0.0276 (8)
H58A	0.6996	0.3574	0.2595	0.033*
H58B	0.7540	0.3601	0.4148	0.033*
C59	0.8233 (3)	0.30182 (12)	0.3248 (3)	0.0255 (8)
C60	0.9602 (4)	0.28759 (13)	0.3737 (3)	0.0298 (8)
H60	1.0274	0.3096	0.4067	0.036*
C61	0.9964 (4)	0.24096 (13)	0.3735 (3)	0.0356 (9)
H61	1.0882	0.2319	0.4056	0.043*
C62	0.8979 (4)	0.20761 (14)	0.3260 (3)	0.0384 (10)
H62	0.9228	0.1762	0.3275	0.046*
C63	0.7621 (4)	0.22115 (14)	0.2763 (4)	0.0380 (9)
H63	0.6952	0.1989	0.2441	0.046*
C64	0.7261 (4)	0.26768 (13)	0.2747 (3)	0.0325 (9)
H64	0.6350	0.2766	0.2395	0.039*
O1	0.3309 (3)	0.21905 (8)	0.2685 (2)	0.0342 (6)
O2	0.6627 (2)	0.43771 (8)	0.5647 (2)	0.0298 (6)
O3	0.4116 (2)	0.36182 (9)	0.7845 (2)	0.0319 (6)
O4	−0.0242 (3)	0.61327 (10)	0.5212 (3)	0.0619 (9)
O5	0.8393 (3)	0.22030 (9)	−0.2012 (2)	0.0390 (6)
O6	1.1596 (2)	0.44863 (8)	0.0834 (2)	0.0326 (6)
O7	0.8971 (2)	0.38020 (8)	0.2972 (2)	0.0258 (5)
N1	0.4250 (2)	0.42119 (10)	0.5347 (2)	0.0215 (6)
N2	0.9258 (3)	0.42805 (10)	0.0370 (2)	0.0219 (6)
O8	0.4500 (3)	0.61465 (9)	−0.0869 (3)	0.0412 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.064 (3)	0.031 (2)	0.038 (2)	−0.011 (2)	0.007 (2)	−0.0052 (17)
C2	0.0277 (19)	0.023 (2)	0.0313 (19)	−0.0009 (15)	0.0109 (15)	0.0013 (16)
C3	0.0307 (19)	0.032 (2)	0.0224 (17)	−0.0040 (16)	0.0043 (14)	−0.0008 (16)
C4	0.0244 (18)	0.028 (2)	0.0238 (17)	−0.0021 (15)	0.0049 (14)	0.0022 (15)
C5	0.0199 (16)	0.0258 (19)	0.0166 (15)	0.0004 (14)	0.0062 (13)	−0.0025 (14)
C6	0.0282 (19)	0.032 (2)	0.0186 (16)	0.0002 (16)	0.0032 (14)	0.0003 (15)
C7	0.033 (2)	0.031 (2)	0.0252 (18)	0.0024 (17)	0.0063 (15)	0.0082 (16)
C8	0.0213 (17)	0.030 (2)	0.0144 (15)	−0.0006 (14)	0.0032 (13)	−0.0007 (13)
C9	0.0220 (18)	0.025 (2)	0.0278 (17)	−0.0039 (15)	0.0017 (15)	−0.0031 (15)
C10	0.0294 (19)	0.048 (2)	0.0234 (17)	−0.0061 (18)	0.0014 (15)	−0.0053 (17)
C11	0.0260 (18)	0.040 (2)	0.0195 (17)	−0.0036 (16)	0.0062 (14)	−0.0041 (15)
C12	0.0205 (17)	0.032 (2)	0.0245 (17)	−0.0038 (15)	0.0076 (14)	−0.0041 (15)
C13	0.0233 (18)	0.032 (2)	0.0201 (16)	−0.0046 (15)	0.0044 (13)	−0.0098 (15)
C14	0.021 (2)	0.035 (2)	0.077 (3)	−0.0073 (18)	0.0156 (19)	−0.011 (2)
C15	0.033 (2)	0.024 (2)	0.091 (3)	−0.0079 (18)	0.019 (2)	−0.009 (2)
C16	0.030 (2)	0.027 (2)	0.0366 (19)	−0.0041 (16)	0.0077 (16)	−0.0095 (16)
C17	0.0194 (17)	0.032 (2)	0.0195 (16)	−0.0028 (16)	0.0030 (13)	−0.0028 (15)
C18	0.0247 (18)	0.031 (2)	0.0160 (15)	−0.0066 (16)	0.0035 (13)	0.0018 (14)
C19	0.038 (2)	0.025 (2)	0.048 (2)	−0.0058 (18)	0.0065 (18)	−0.0083 (18)
C20	0.0284 (19)	0.025 (2)	0.0386 (19)	0.0005 (15)	0.0017 (16)	−0.0051 (16)
C21	0.045 (2)	0.055 (3)	0.069 (3)	0.002 (2)	0.002 (2)	−0.035 (2)
C22	0.043 (2)	0.044 (3)	0.046 (2)	0.004 (2)	0.0114 (18)	−0.014 (2)
C23	0.037 (2)	0.060 (3)	0.034 (2)	0.014 (2)	0.0033 (17)	0.0076 (19)
C24	0.047 (3)	0.100 (4)	0.038 (2)	0.017 (3)	−0.005 (2)	−0.026 (2)
C25	0.044 (2)	0.069 (3)	0.033 (2)	0.019 (2)	0.0019 (18)	−0.009 (2)
C26	0.033 (2)	0.053 (3)	0.037 (2)	−0.0020 (19)	0.0148 (17)	0.0120 (19)
C27	0.038 (2)	0.047 (2)	0.0262 (18)	0.002 (2)	0.0161 (16)	0.0091 (17)
C28	0.033 (2)	0.045 (3)	0.054 (2)	0.0050 (19)	0.0184 (19)	0.008 (2)
C29	0.050 (3)	0.070 (4)	0.059 (3)	0.013 (3)	0.027 (2)	0.007 (3)
C30	0.071 (3)	0.049 (3)	0.054 (3)	0.006 (3)	0.032 (2)	−0.006 (2)
C31	0.064 (3)	0.055 (3)	0.041 (2)	−0.015 (2)	0.020 (2)	−0.006 (2)
C32	0.046 (3)	0.054 (3)	0.033 (2)	0.000 (2)	0.0133 (18)	0.0033 (19)
C33	0.077 (3)	0.036 (2)	0.039 (2)	−0.006 (2)	0.013 (2)	−0.0042 (19)
C34	0.032 (2)	0.027 (2)	0.0318 (19)	0.0035 (16)	0.0149 (16)	−0.0018 (16)
C35	0.033 (2)	0.036 (2)	0.0206 (17)	−0.0036 (17)	0.0075 (15)	−0.0034 (16)
C36	0.0263 (18)	0.036 (2)	0.0178 (16)	0.0048 (16)	0.0067 (14)	0.0059 (16)
C37	0.0210 (17)	0.031 (2)	0.0194 (16)	0.0019 (15)	0.0079 (14)	0.0018 (14)
C38	0.0272 (19)	0.037 (2)	0.0189 (17)	0.0048 (16)	0.0053 (14)	−0.0001 (16)
C39	0.036 (2)	0.037 (2)	0.0251 (18)	0.0073 (18)	0.0050 (16)	0.0050 (16)
C40	0.0237 (17)	0.033 (2)	0.0163 (15)	0.0026 (15)	0.0064 (13)	0.0037 (14)
C41	0.0233 (19)	0.0219 (18)	0.0241 (17)	−0.0001 (15)	−0.0002 (15)	0.0101 (14)
C42	0.0272 (18)	0.030 (2)	0.0213 (16)	−0.0034 (16)	0.0011 (14)	0.0006 (14)
C43	0.0299 (18)	0.0212 (19)	0.0173 (15)	0.0028 (15)	0.0051 (13)	0.0012 (14)
C44	0.0189 (16)	0.0198 (18)	0.0212 (16)	−0.0012 (14)	0.0072 (13)	0.0018 (14)
C45	0.0196 (17)	0.0259 (19)	0.0151 (14)	−0.0031 (14)	0.0038 (13)	−0.0055 (14)
C46	0.0193 (18)	0.028 (2)	0.0315 (18)	−0.0035 (15)	0.0003 (14)	0.0010 (15)
C47	0.0296 (19)	0.027 (2)	0.0275 (17)	−0.0059 (16)	0.0042 (15)	0.0019 (15)
C48	0.0239 (18)	0.0206 (18)	0.0234 (16)	−0.0007 (14)	0.0024 (13)	−0.0003 (14)
C49	0.0207 (17)	0.027 (2)	0.0173 (15)	−0.0005 (15)	0.0040 (13)	−0.0028 (14)
C50	0.0230 (18)	0.0272 (19)	0.0156 (15)	−0.0046 (15)	0.0052 (13)	−0.0013 (14)
C51	0.034 (2)	0.024 (2)	0.0268 (18)	−0.0029 (17)	0.0055 (15)	−0.0021 (15)
C52	0.0243 (18)	0.0178 (18)	0.0325 (18)	0.0011 (15)	0.0019 (15)	0.0008 (15)
C53	0.0332 (19)	0.032 (2)	0.0314 (18)	0.0024 (17)	0.0019 (16)	0.0038 (16)
C54	0.032 (2)	0.027 (2)	0.044 (2)	0.0041 (17)	−0.0043 (17)	−0.0009 (18)
C55	0.0286 (19)	0.024 (2)	0.051 (2)	−0.0002 (16)	0.0080 (16)	−0.0042 (17)
C56	0.032 (2)	0.037 (2)	0.0346 (19)	0.0016 (17)	0.0099 (16)	−0.0052 (16)
C57	0.0285 (19)	0.036 (2)	0.0274 (18)	0.0003 (16)	0.0006 (15)	0.0007 (15)
C58	0.0299 (19)	0.029 (2)	0.0253 (17)	0.0004 (16)	0.0100 (15)	0.0035 (15)
C59	0.0286 (18)	0.030 (2)	0.0195 (16)	0.0001 (16)	0.0108 (14)	0.0044 (15)
C60	0.035 (2)	0.028 (2)	0.0286 (18)	0.0009 (17)	0.0104 (15)	−0.0003 (16)
C61	0.032 (2)	0.040 (2)	0.036 (2)	0.0064 (18)	0.0103 (16)	0.0043 (17)
C62	0.050 (3)	0.030 (2)	0.037 (2)	0.0064 (19)	0.0125 (19)	−0.0038 (17)
C63	0.041 (2)	0.034 (2)	0.041 (2)	−0.0049 (19)	0.0116 (18)	−0.0035 (18)
C64	0.030 (2)	0.038 (2)	0.0308 (19)	−0.0014 (18)	0.0096 (16)	−0.0017 (17)
O1	0.0473 (16)	0.0222 (14)	0.0343 (13)	−0.0019 (11)	0.0095 (11)	−0.0026 (11)
O2	0.0232 (13)	0.0340 (15)	0.0327 (13)	−0.0076 (11)	0.0062 (10)	0.0014 (11)
O3	0.0292 (13)	0.0431 (17)	0.0244 (12)	0.0000 (12)	0.0070 (10)	0.0093 (11)
O4	0.0408 (17)	0.0285 (17)	0.117 (3)	−0.0060 (14)	0.0120 (16)	−0.0074 (17)
O5	0.0519 (17)	0.0327 (16)	0.0340 (13)	0.0044 (13)	0.0111 (12)	−0.0021 (12)
O6	0.0226 (13)	0.0391 (15)	0.0368 (14)	−0.0047 (11)	0.0069 (11)	0.0110 (11)
O7	0.0250 (12)	0.0279 (14)	0.0254 (12)	−0.0007 (10)	0.0067 (10)	0.0067 (10)
N1	0.0167 (13)	0.0323 (16)	0.0162 (12)	−0.0066 (12)	0.0052 (11)	−0.0039 (12)
N2	0.0184 (14)	0.0318 (17)	0.0163 (12)	−0.0017 (12)	0.0049 (11)	0.0012 (12)
O8	0.0370 (15)	0.0243 (15)	0.0645 (17)	0.0000 (12)	0.0147 (12)	0.0103 (13)

Geometric parameters (Å, º) top

C1—O1	1.425 (4)	C33—O5	1.432 (4)
C1—H1A	0.9600	C33—H33A	0.9600
C1—H1B	0.9600	C33—H33B	0.9600
C1—H1C	0.9600	C33—H33C	0.9600
C2—O1	1.368 (4)	C34—O5	1.372 (4)
C2—C7	1.385 (5)	C34—C39	1.390 (5)
C2—C3	1.397 (5)	C34—C35	1.394 (5)
C3—C4	1.391 (5)	C35—C36	1.387 (5)
C3—H3	0.9300	C35—H35	0.9300
C4—C5	1.383 (4)	C36—C37	1.390 (4)
C4—H4	0.9300	C36—H36	0.9300
C5—C6	1.406 (5)	C37—C38	1.398 (5)
C5—C8	1.508 (5)	C37—C40	1.512 (5)
C6—C7	1.375 (5)	C38—C39	1.381 (5)
C6—H6	0.9300	C38—H38	0.9300
C7—H7	0.9300	C39—H39	0.9300
C8—N1	1.456 (4)	C40—N2	1.455 (4)
C8—H8A	0.9700	C40—H40A	0.9700
C8—H8B	0.9700	C40—H40B	0.9700
C9—O2	1.226 (4)	C41—O6	1.224 (4)
C9—N1	1.349 (4)	C41—N2	1.352 (4)
C9—C10	1.514 (4)	C41—C42	1.511 (4)
C10—C11	1.514 (5)	C42—C43	1.518 (4)
C10—H10A	0.9700	C42—H42A	0.9700
C10—H10B	0.9700	C42—H42B	0.9700
C11—O3	1.420 (4)	C43—O7	1.429 (4)
C11—C12	1.559 (4)	C43—C44	1.556 (4)
C11—H11	0.9800	C43—H43	0.9800
C12—N1	1.461 (4)	C44—N2	1.455 (4)
C12—C13	1.504 (5)	C44—C45	1.517 (4)
C12—H12	0.9800	C44—H44	0.9800
C13—C14	1.380 (5)	C45—C50	1.385 (4)
C13—C18	1.390 (5)	C45—C46	1.400 (5)
C14—C15	1.377 (5)	C46—C47	1.378 (5)
C14—H14	0.9300	C46—H46	0.9300
C15—C16	1.388 (5)	C47—C48	1.383 (4)
C15—H15	0.9300	C47—H47	0.9300
C16—C17	1.380 (5)	C48—C49	1.400 (5)
C16—C19	1.497 (5)	C48—C51	1.507 (5)
C17—C18	1.382 (5)	C49—C50	1.389 (5)
C17—H17	0.9300	C49—H49	0.9300
C18—H18	0.9300	C50—H50	0.9300
C19—O4	1.239 (5)	C51—O8	1.219 (4)
C19—C20	1.499 (5)	C51—C52	1.515 (5)
C20—C25	1.500 (5)	C52—C57	1.526 (5)
C20—C21	1.504 (5)	C52—C53	1.529 (4)
C20—H20	0.9800	C52—H52	0.9800
C21—C22	1.529 (5)	C53—C54	1.524 (5)
C21—H21A	0.9700	C53—H53A	0.9700
C21—H21B	0.9700	C53—H53B	0.9700
C22—C23	1.502 (5)	C54—C55	1.513 (5)
C22—H22A	0.9700	C54—H54A	0.9700
C22—H22B	0.9700	C54—H54B	0.9700
C23—C24	1.526 (6)	C55—C56	1.517 (5)
C23—H23A	0.9700	C55—H55A	0.9700
C23—H23B	0.9700	C55—H55B	0.9700
C24—C25	1.539 (6)	C56—C57	1.525 (5)
C24—H24A	0.9700	C56—H56A	0.9700
C24—H24B	0.9700	C56—H56B	0.9700
C25—H25A	0.9700	C57—H57A	0.9700
C25—H25B	0.9700	C57—H57B	0.9700
C26—O3	1.432 (4)	C58—O7	1.428 (4)
C26—C27	1.511 (6)	C58—C59	1.494 (5)
C26—H26A	0.9700	C58—H58A	0.9700
C26—H26B	0.9700	C58—H58B	0.9700
C27—C32	1.376 (5)	C59—C60	1.395 (5)
C27—C28	1.392 (5)	C59—C64	1.396 (5)
C28—C29	1.389 (6)	C60—C61	1.379 (5)
C28—H28	0.9300	C60—H60	0.9300
C29—C30	1.383 (6)	C61—C62	1.381 (5)
C29—H29	0.9300	C61—H61	0.9300
C30—C31	1.367 (6)	C62—C63	1.382 (5)
C30—H30	0.9300	C62—H62	0.9300
C31—C32	1.385 (6)	C63—C64	1.376 (5)
C31—H31	0.9300	C63—H63	0.9300
C32—H32	0.9300	C64—H64	0.9300

O1—C1—H1A	109.5	H33B—C33—H33C	109.5
O1—C1—H1B	109.5	O5—C34—C39	116.5 (3)
H1A—C1—H1B	109.5	O5—C34—C35	123.8 (3)
O1—C1—H1C	109.5	C39—C34—C35	119.7 (3)
H1A—C1—H1C	109.5	C36—C35—C34	119.3 (3)
H1B—C1—H1C	109.5	C36—C35—H35	120.4
O1—C2—C7	116.1 (3)	C34—C35—H35	120.4
O1—C2—C3	124.6 (3)	C35—C36—C37	122.0 (3)
C7—C2—C3	119.3 (3)	C35—C36—H36	119.0
C4—C3—C2	119.2 (3)	C37—C36—H36	119.0
C4—C3—H3	120.4	C36—C37—C38	117.6 (3)
C2—C3—H3	120.4	C36—C37—C40	120.1 (3)
C5—C4—C3	122.1 (3)	C38—C37—C40	122.3 (3)
C5—C4—H4	118.9	C39—C38—C37	121.3 (3)
C3—C4—H4	118.9	C39—C38—H38	119.3
C4—C5—C6	117.5 (3)	C37—C38—H38	119.3
C4—C5—C8	120.5 (3)	C38—C39—C34	120.1 (3)
C6—C5—C8	122.0 (3)	C38—C39—H39	120.0
C7—C6—C5	121.0 (3)	C34—C39—H39	120.0
C7—C6—H6	119.5	N2—C40—C37	113.2 (3)
C5—C6—H6	119.5	N2—C40—H40A	108.9
C6—C7—C2	120.7 (3)	C37—C40—H40A	108.9
C6—C7—H7	119.6	N2—C40—H40B	108.9
C2—C7—H7	119.6	C37—C40—H40B	108.9
N1—C8—C5	112.4 (3)	H40A—C40—H40B	107.7
N1—C8—H8A	109.1	O6—C41—N2	125.4 (3)
C5—C8—H8A	109.1	O6—C41—C42	127.0 (3)
N1—C8—H8B	109.1	N2—C41—C42	107.6 (3)
C5—C8—H8B	109.1	C41—C42—C43	104.0 (2)
H8A—C8—H8B	107.8	C41—C42—H42A	111.0
O2—C9—N1	125.7 (3)	C43—C42—H42A	111.0
O2—C9—C10	126.9 (3)	C41—C42—H42B	111.0
N1—C9—C10	107.5 (3)	C43—C42—H42B	111.0
C9—C10—C11	104.7 (3)	H42A—C42—H42B	109.0
C9—C10—H10A	110.8	O7—C43—C42	105.4 (2)
C11—C10—H10A	110.8	O7—C43—C44	109.6 (2)
C9—C10—H10B	110.8	C42—C43—C44	103.1 (2)
C11—C10—H10B	110.8	O7—C43—H43	112.7
H10A—C10—H10B	108.9	C42—C43—H43	112.7
O3—C11—C10	106.8 (3)	C44—C43—H43	112.7
O3—C11—C12	110.4 (3)	N2—C44—C45	113.9 (3)
C10—C11—C12	103.2 (3)	N2—C44—C43	101.7 (2)
O3—C11—H11	112.0	C45—C44—C43	113.1 (2)
C10—C11—H11	112.0	N2—C44—H44	109.3
C12—C11—H11	112.0	C45—C44—H44	109.3
N1—C12—C13	113.1 (3)	C43—C44—H44	109.3
N1—C12—C11	102.0 (2)	C50—C45—C46	118.3 (3)
C13—C12—C11	114.2 (3)	C50—C45—C44	119.6 (3)
N1—C12—H12	109.1	C46—C45—C44	122.1 (3)
C13—C12—H12	109.1	C47—C46—C45	120.5 (3)
C11—C12—H12	109.1	C47—C46—H46	119.8
C14—C13—C18	118.0 (3)	C45—C46—H46	119.8
C14—C13—C12	121.7 (3)	C46—C47—C48	121.3 (3)
C18—C13—C12	120.4 (3)	C46—C47—H47	119.3
C15—C14—C13	121.2 (3)	C48—C47—H47	119.3
C15—C14—H14	119.4	C47—C48—C49	118.7 (3)
C13—C14—H14	119.4	C47—C48—C51	118.4 (3)
C14—C15—C16	120.6 (4)	C49—C48—C51	122.9 (3)
C14—C15—H15	119.7	C50—C49—C48	119.8 (3)
C16—C15—H15	119.7	C50—C49—H49	120.1
C17—C16—C15	118.7 (3)	C48—C49—H49	120.1
C17—C16—C19	123.2 (3)	C45—C50—C49	121.4 (3)
C15—C16—C19	118.1 (3)	C45—C50—H50	119.3
C16—C17—C18	120.3 (3)	C49—C50—H50	119.3
C16—C17—H17	119.9	O8—C51—C48	119.4 (3)
C18—C17—H17	119.9	O8—C51—C52	120.8 (3)
C17—C18—C13	121.2 (3)	C48—C51—C52	119.8 (3)
C17—C18—H18	119.4	C51—C52—C57	109.9 (2)
C13—C18—H18	119.4	C51—C52—C53	111.4 (3)
O4—C19—C16	119.1 (3)	C57—C52—C53	109.3 (3)
O4—C19—C20	119.7 (3)	C51—C52—H52	108.8
C16—C19—C20	121.0 (3)	C57—C52—H52	108.8
C19—C20—C25	107.4 (3)	C53—C52—H52	108.8
C19—C20—C21	113.5 (3)	C54—C53—C52	111.3 (3)
C25—C20—C21	112.1 (3)	C54—C53—H53A	109.4
C19—C20—H20	107.9	C52—C53—H53A	109.4
C25—C20—H20	107.9	C54—C53—H53B	109.4
C21—C20—H20	107.9	C52—C53—H53B	109.4
C20—C21—C22	112.2 (3)	H53A—C53—H53B	108.0
C20—C21—H21A	109.2	C55—C54—C53	110.9 (3)
C22—C21—H21A	109.2	C55—C54—H54A	109.5
C20—C21—H21B	109.2	C53—C54—H54A	109.5
C22—C21—H21B	109.2	C55—C54—H54B	109.5
H21A—C21—H21B	107.9	C53—C54—H54B	109.5
C23—C22—C21	110.2 (3)	H54A—C54—H54B	108.1
C23—C22—H22A	109.6	C54—C55—C56	111.1 (3)
C21—C22—H22A	109.6	C54—C55—H55A	109.4
C23—C22—H22B	109.6	C56—C55—H55A	109.4
C21—C22—H22B	109.6	C54—C55—H55B	109.4
H22A—C22—H22B	108.1	C56—C55—H55B	109.4
C22—C23—C24	111.2 (3)	H55A—C55—H55B	108.0
C22—C23—H23A	109.4	C55—C56—C57	112.0 (3)
C24—C23—H23A	109.4	C55—C56—H56A	109.2
C22—C23—H23B	109.4	C57—C56—H56A	109.2
C24—C23—H23B	109.4	C55—C56—H56B	109.2
H23A—C23—H23B	108.0	C57—C56—H56B	109.2
C23—C24—C25	110.1 (4)	H56A—C56—H56B	107.9
C23—C24—H24A	109.6	C56—C57—C52	111.9 (3)
C25—C24—H24A	109.6	C56—C57—H57A	109.2
C23—C24—H24B	109.6	C52—C57—H57A	109.2
C25—C24—H24B	109.6	C56—C57—H57B	109.2
H24A—C24—H24B	108.2	C52—C57—H57B	109.2
C20—C25—C24	110.3 (3)	H57A—C57—H57B	107.9
C20—C25—H25A	109.6	O7—C58—C59	108.9 (3)
C24—C25—H25A	109.6	O7—C58—H58A	109.9
C20—C25—H25B	109.6	C59—C58—H58A	109.9
C24—C25—H25B	109.6	O7—C58—H58B	109.9
H25A—C25—H25B	108.1	C59—C58—H58B	109.9
O3—C26—C27	109.5 (3)	H58A—C58—H58B	108.3
O3—C26—H26A	109.8	C60—C59—C64	118.0 (3)
C27—C26—H26A	109.8	C60—C59—C58	121.4 (3)
O3—C26—H26B	109.8	C64—C59—C58	120.6 (3)
C27—C26—H26B	109.8	C61—C60—C59	120.3 (3)
H26A—C26—H26B	108.2	C61—C60—H60	119.8
C32—C27—C28	119.2 (4)	C59—C60—H60	119.8
C32—C27—C26	120.3 (3)	C60—C61—C62	120.8 (3)
C28—C27—C26	120.5 (4)	C60—C61—H61	119.6
C29—C28—C27	119.6 (4)	C62—C61—H61	119.6
C29—C28—H28	120.2	C61—C62—C63	119.6 (4)
C27—C28—H28	120.2	C61—C62—H62	120.2
C30—C29—C28	120.3 (4)	C63—C62—H62	120.2
C30—C29—H29	119.9	C64—C63—C62	119.8 (4)
C28—C29—H29	119.9	C64—C63—H63	120.1
C31—C30—C29	120.0 (5)	C62—C63—H63	120.1
C31—C30—H30	120.0	C63—C64—C59	121.5 (3)
C29—C30—H30	120.0	C63—C64—H64	119.3
C30—C31—C32	119.9 (4)	C59—C64—H64	119.3
C30—C31—H31	120.0	C2—O1—C1	117.1 (3)
C32—C31—H31	120.0	C11—O3—C26	114.1 (3)
C27—C32—C31	121.0 (4)	C34—O5—C33	117.9 (3)
C27—C32—H32	119.5	C58—O7—C43	113.6 (2)
C31—C32—H32	119.5	C9—N1—C8	123.1 (3)
O5—C33—H33A	109.5	C9—N1—C12	114.3 (2)
O5—C33—H33B	109.5	C8—N1—C12	122.3 (2)
H33A—C33—H33B	109.5	C41—N2—C44	114.2 (2)
O5—C33—H33C	109.5	C41—N2—C40	123.2 (3)
H33A—C33—H33C	109.5	C44—N2—C40	122.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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−1/2, −z+1; (ii) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C62—H62···O4ⁱ	0.93	2.47	3.260 (5)	142.7
C17—H17···O2ⁱⁱ	0.93	2.38	3.237 (4)	153.2
C49—H49···O6ⁱⁱ	0.93	2.33	3.190 (4)	154.1

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x−1, y, z.

Acknowledgements

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

References

Hu, 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
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shiue, J.-S., Lin, M.-H. & Fang, J.-M. (1997). J. Org. Chem. 62, 4643–4649. CrossRef CAS Web of Science Google Scholar
Zheng, X., Feng, C.-G. & Huang, P.-Q. (2005). Org. Lett. 7, 553–556. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 70| Part 4| April 2014| Pages o419-o420

doi:10.1107/S1600536814003638

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

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

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organic compounds

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