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

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ISSN: 2056-9890

(E)-N-[2-(3,5-Di-tert-butyl-2-hy­droxy­benzyl­­idene­amino)cyclo­hexyl]-4-methyl­benzene­sulfonamide

aCollege of Chemistry and Chemical Engineering, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China
*Correspondence e-mail: wujc@lzu.edu.cn

(Received 20 December 2008; accepted 24 December 2008; online 8 January 2009)

In the crystal structure of the title compound, C28H40N2O3S, there are two mol­ecules per asymmetric unit; in each of these mol­ecules, the cyclo­hexyl rings adopt chair conformations. The dihedral angles between the benzene rings are 16.89 (9) and 34.11 (9)°. Each mol­ecule contains an intra­molecular O—H⋯N hydrogen bond, and inter­molecular N—H⋯O hydrogen bonds are also present. In both mol­ecules, the methyl groups of one tert-butyl group are disordered over two positions; the site-occupancy factors in both cases are ca 0.6 and 0.4.

Related literature

For the polymerization of cyclic esters, see: Endo et al. (1987[Endo, M., Aida, T. & Inoue, S. (1987). Macromolecules, 20, 2982-2988.]); Wu et al. (2006[Wu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602-626.]). For synthetic details, see: Balsells et al. (1998[Balsells, J., Mejorado, L., Phillips, M., Ortega, F., Aguirre, G., Somanathan, R. & Walsh, P. J. (1998). Tetrahedron Asymmetry, 9, 4135-4142.]).

[Scheme 1]

Experimental

Crystal data
  • C28H40N2O3S

  • Mr = 484.68

  • Monoclinic, P 21

  • a = 10.3873 (10) Å

  • b = 25.773 (2) Å

  • c = 10.4127 (10) Å

  • β = 97.269 (2)°

  • V = 2765.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.15 mm−1

  • T = 298 (2) K

  • 0.35 × 0.30 × 0.21 mm

Data collection
  • Bruker SMART 1K CCD diffractometer

  • Absorption correction: multi-scan (MULscanABS in SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.]) Tmin = 0.950, Tmax = 0.970

  • 15079 measured reflections

  • 9696 independent reflections

  • 7043 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.119

  • S = 0.97

  • 9696 reflections

  • 689 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.25 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4173 Friedel pairs

  • Flack parameter: −0.04 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.82 1.89 2.621 (3) 149
O4—H4A⋯N3 0.82 1.88 2.619 (3) 149
N2—H2B⋯O5i 0.86 2.36 2.987 (3) 130
N4—H4B⋯O2ii 0.86 2.30 2.950 (3) 133
Symmetry codes: (i) x, y, z-1; (ii) x, y, z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]) and local programs.

Supporting information


Comment top

Recently, significant advances have been made in the polymerization of cyclic esters, such as poly-ε-caprolactone (Endo et al., 1987), polylactide (Wu et al., 2006) A particularly convenient method for the synthesis of polylactides is the ring-opening polymerization (ROP) of lactides. Due to the advantages of well-controlled molecular weight and low polydispersity (PDI), many metal complexes have been used. In the present study, we report a structure which is a potential ligand for the investigation of ROP of lactides.

As shown in Fig. 1, the asymmetric unit contains two molecules. In each of these molecules the cyclohexyl rings adopt chair conformations. The dihedral angles between the benzene rings are 16.89 (9)° and 34.11 (9)°. The bond lengths and angles are within normal ranges. Each molecule contains an intramolecular O—H···N hydrogen bond and intermolecular N—H···O hydrogen bonds are also present (Table 1 and Fig. 2). A short contact O2···.C43, with a distance of 3.011 (4) Å, involves the interaction of S=O and C=N.

Related literature top

For the polymerization of cyclic esters, see: Endo et al. (1987); Wu et al. (2006). For synthetic details, see: Balsells et al. (1998).

Experimental top

The title compound was prepared as described in the literature (Balsells et al., 1998). A fine crystal was obtained from an acetonitrile solution.

Refinement top

H atoms were placed in caculated positions and refined using a riding model, with d(N—H) = 0.86 Å and Uiso(H) = 1.2Ueq(N), d(O—H) = 0.82 Å and Uiso(H) = 1.2Ueq(O), d(C—H) = 0.93 Å and Uiso(H) = 1.2Ueq(C) for Csp2, d(C—H) = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene groups, and d(C—H) = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl groups.

PLATON (Spek, 2003) suggests four A level alerts and two B level alerts which result from the disorder of tert-butyl groups. In both molecules the methyl groups of one tert-butyl group are disordered over two positions. The site occupancy factors for C8, C9, C10 and attached H atoms are 0.62 (2) and 0.38 (2); for C36, C37, C38 and attached H atoms the values are 0.621 (13) and 0.379 (13).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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), PLATON (Spek, 2003) and local programs.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. The minor positions of the disordered tert-butyl groups are not shown.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the c axis, showing hydrogen bonds (dashed lines). H atoms have been omitted. The minor positions of the disordered tert-butyl groups are not shown.
(E)-N-[2-(3,5-Di-tert-butyl-2- hydroxybenzylideneamino)cyclohexyl]-4-methylbenzenesulfonamide top
Crystal data top
C28H40N2O3SF(000) = 1048
Mr = 484.68Dx = 1.164 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 973 reflections
a = 10.3873 (10) Åθ = 2.5–24.9°
b = 25.773 (2) ŵ = 0.15 mm1
c = 10.4127 (10) ÅT = 298 K
β = 97.269 (2)°Block, yellow
V = 2765.2 (4) Å30.35 × 0.30 × 0.21 mm
Z = 4
Data collection top
Bruker SMART 1K CCD
diffractometer
9696 independent reflections
Radiation source: fine-focus sealed tube7043 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ϕ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(MULscanABS in SADABS; Sheldrick, 2002)
h = 129
Tmin = 0.950, Tmax = 0.970k = 3123
15079 measured reflectionsl = 1212
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.0663P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.119(Δ/σ)max = 0.046
S = 0.97Δρmax = 0.26 e Å3
9696 reflectionsΔρmin = 0.25 e Å3
689 parametersExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0038 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 4173 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.04 (6)
Crystal data top
C28H40N2O3SV = 2765.2 (4) Å3
Mr = 484.68Z = 4
Monoclinic, P21Mo Kα radiation
a = 10.3873 (10) ŵ = 0.15 mm1
b = 25.773 (2) ÅT = 298 K
c = 10.4127 (10) Å0.35 × 0.30 × 0.21 mm
β = 97.269 (2)°
Data collection top
Bruker SMART 1K CCD
diffractometer
9696 independent reflections
Absorption correction: multi-scan
(MULscanABS in SADABS; Sheldrick, 2002)
7043 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.970Rint = 0.034
15079 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.119Δρmax = 0.26 e Å3
S = 0.97Δρmin = 0.25 e Å3
9696 reflectionsAbsolute structure: Flack (1983), 4173 Friedel pairs
689 parametersAbsolute structure parameter: 0.04 (6)
1 restraint
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)
S10.14819 (7)0.14435 (3)0.18423 (8)0.0499 (2)
S20.58237 (7)0.15336 (3)0.83633 (8)0.0513 (2)
O10.29301 (19)0.30301 (9)0.1795 (2)0.0526 (6)
H10.25690.29970.10520.079*
O20.2506 (2)0.10829 (8)0.2013 (2)0.0631 (6)
O30.0211 (2)0.13451 (8)0.2487 (2)0.0621 (6)
O40.42726 (19)0.00727 (9)0.4676 (2)0.0532 (6)
H4A0.46380.00440.54180.080*
O50.4811 (2)0.18955 (8)0.8563 (2)0.0625 (6)
O60.7097 (2)0.16206 (10)0.9016 (2)0.0661 (7)
N10.2698 (2)0.29414 (10)0.0732 (2)0.0432 (6)
N20.1968 (2)0.20004 (9)0.2292 (2)0.0460 (6)
H2B0.27160.20310.25540.055*
N30.4524 (2)0.00504 (9)0.7192 (2)0.0432 (6)
N40.5323 (2)0.09751 (10)0.8777 (3)0.0478 (6)
H4B0.45660.09490.90230.057*
C10.4230 (3)0.30549 (11)0.1781 (3)0.0395 (7)
C60.5057 (3)0.31103 (11)0.2961 (3)0.0410 (7)
C110.4510 (3)0.31494 (12)0.4264 (3)0.0461 (8)
C140.3715 (4)0.26723 (13)0.4496 (3)0.0611 (9)
H14A0.34090.26990.53250.092*
H14B0.42460.23680.44780.092*
H14C0.29880.26480.38310.092*
C120.3668 (4)0.36364 (15)0.4286 (4)0.0722 (11)
H12A0.32830.36450.50770.108*
H12B0.29960.36300.35630.108*
H12C0.41960.39390.42330.108*
C130.5605 (4)0.31917 (16)0.5397 (3)0.0707 (11)
H13A0.52380.32170.61960.106*
H13B0.61150.34960.52890.106*
H13C0.61470.28890.54160.106*
C50.6368 (3)0.31371 (12)0.2871 (3)0.0463 (7)
H5B0.69220.31800.36380.056*
C40.6939 (3)0.31053 (13)0.1725 (3)0.0475 (7)
C70.8414 (3)0.31449 (16)0.1737 (4)0.0644 (10)
C80.8870 (9)0.3671 (5)0.2409 (16)0.113 (4)0.62 (2)
H8A0.86710.36710.32850.169*0.62 (2)
H8B0.84290.39540.19430.169*0.62 (2)
H8C0.97900.37090.24100.169*0.62 (2)
C90.8846 (12)0.3123 (8)0.0409 (11)0.117 (7)0.62 (2)
H9A0.85140.28130.00260.176*0.62 (2)
H9B0.97770.31210.04890.176*0.62 (2)
H9C0.85210.34210.00820.176*0.62 (2)
C100.9056 (11)0.2708 (5)0.2644 (12)0.081 (3)0.62 (2)
H10A0.88150.23750.22770.121*0.62 (2)
H10B0.87630.27370.34800.121*0.62 (2)
H10C0.99830.27450.27330.121*0.62 (2)
C9'0.8752 (17)0.3694 (8)0.128 (5)0.161 (17)0.38 (2)
H9'A0.86780.39390.19620.242*0.38 (2)
H9'B0.81620.37880.05310.242*0.38 (2)
H9'C0.96240.36960.10680.242*0.38 (2)
C11'0.8800 (17)0.2763 (16)0.065 (4)0.155 (14)0.38 (2)
H11A0.93170.24840.10550.232*0.38 (2)
H11B0.92890.29490.00810.232*0.38 (2)
H11C0.80280.26240.01720.232*0.38 (2)
C10'0.927 (2)0.302 (2)0.293 (4)0.21 (2)0.38 (2)
H10D0.90710.26830.32300.310*0.38 (2)
H10E0.91460.32740.35880.310*0.38 (2)
H10F1.01600.30320.27670.310*0.38 (2)
C30.6092 (3)0.30536 (13)0.0596 (3)0.0474 (7)
H3C0.64230.30390.01920.057*
C20.4751 (3)0.30228 (11)0.0611 (3)0.0405 (7)
C150.3927 (3)0.29867 (12)0.0627 (3)0.0436 (7)
H15A0.43210.29970.13810.052*
C160.1941 (3)0.29483 (12)0.2025 (3)0.0424 (7)
H16A0.25380.29680.26810.051*
C170.1084 (3)0.34361 (13)0.2118 (3)0.0585 (9)
H17A0.06050.34460.13770.070*
H17B0.16380.37400.20760.070*
C180.0129 (4)0.34630 (15)0.3347 (4)0.0665 (10)
H18A0.05980.35060.40880.080*
H18B0.04370.37610.33070.080*
C190.0682 (3)0.29699 (15)0.3505 (3)0.0596 (10)
H19A0.12000.29400.27970.072*
H19B0.12660.29850.43080.072*
C200.0193 (3)0.25048 (13)0.3517 (3)0.0521 (8)
H20A0.06970.25340.42370.063*
H20B0.03330.21930.36440.063*
C210.1116 (3)0.24572 (12)0.2249 (3)0.0418 (7)
H21A0.06000.24160.15300.050*
C220.1358 (3)0.14887 (13)0.0177 (3)0.0453 (7)
C230.0238 (3)0.13469 (14)0.0282 (4)0.0661 (10)
H23A0.04810.12460.02870.079*
C240.0178 (4)0.13548 (16)0.1614 (4)0.0728 (11)
H24A0.05780.12470.19250.087*
C250.1218 (3)0.15193 (14)0.2483 (3)0.0601 (9)
C280.1151 (4)0.15085 (19)0.3919 (4)0.0866 (13)
H28A0.11290.11550.42060.130*
H28B0.03820.16850.41030.130*
H28C0.19010.16790.43630.130*
C260.2312 (3)0.16790 (13)0.1981 (4)0.0584 (9)
H26A0.30140.18020.25420.070*
C270.2404 (3)0.16632 (13)0.0671 (3)0.0547 (9)
H27A0.31630.17690.03590.066*
C290.2970 (3)0.00411 (11)0.4683 (3)0.0388 (6)
C340.2129 (3)0.00827 (11)0.3516 (3)0.0399 (7)
C390.2657 (3)0.01707 (13)0.2213 (3)0.0474 (8)
C420.3567 (4)0.02754 (16)0.1953 (4)0.0709 (11)
H42A0.42430.03070.26670.106*
H42B0.30830.05930.18530.106*
H42C0.39440.02050.11750.106*
C400.3388 (4)0.06865 (15)0.2242 (4)0.0707 (11)
H40A0.41120.06770.29140.106*
H40B0.36970.07420.14220.106*
H40C0.28150.09640.24080.106*
C410.1576 (4)0.01910 (18)0.1074 (3)0.0726 (11)
H41A0.11170.01330.10110.109*
H41B0.09850.04670.12070.109*
H41C0.19450.02520.02880.109*
C330.0807 (3)0.00399 (11)0.3594 (3)0.0415 (7)
H33A0.02430.00610.28270.050*
C320.0265 (3)0.00322 (12)0.4744 (3)0.0437 (7)
C350.1219 (3)0.00781 (13)0.4743 (3)0.0495 (8)
C360.1717 (6)0.0548 (3)0.3839 (10)0.079 (3)0.621 (13)
H36A0.14210.05070.30080.119*0.621 (13)
H36B0.13840.08670.42250.119*0.621 (13)
H36C0.26480.05560.37350.119*0.621 (13)
C370.1884 (10)0.0400 (3)0.4122 (12)0.083 (4)0.621 (13)
H37A0.17030.04280.32430.125*0.621 (13)
H37B0.28040.03710.41330.125*0.621 (13)
H37C0.15670.07030.45960.125*0.621 (13)
C380.1624 (7)0.0177 (5)0.6022 (7)0.102 (5)0.621 (13)
H38A0.11330.04610.64280.154*0.621 (13)
H38B0.14740.01280.65500.154*0.621 (13)
H38C0.25310.02610.59240.154*0.621 (13)
C36'0.1500 (12)0.0580 (6)0.529 (3)0.132 (11)0.379 (13)
H36D0.08790.08310.50770.199*0.379 (13)
H36E0.14500.05500.62150.199*0.379 (13)
H36F0.23570.06890.49420.199*0.379 (13)
C37'0.1975 (16)0.0086 (14)0.358 (2)0.166 (16)0.379 (13)
H37D0.19140.01670.29120.249*0.379 (13)
H37E0.28650.01230.37230.249*0.379 (13)
H37F0.16560.04140.33130.249*0.379 (13)
C38'0.1498 (12)0.0362 (8)0.5812 (18)0.116 (7)0.379 (13)
H38D0.09520.06580.57320.174*0.379 (13)
H38E0.23920.04660.56620.174*0.379 (13)
H38F0.13130.02200.66670.174*0.379 (13)
C310.1115 (3)0.00599 (12)0.5857 (3)0.0447 (7)
H31A0.07880.01060.66400.054*
C300.2460 (3)0.00212 (11)0.5860 (3)0.0395 (7)
C430.3298 (3)0.00341 (12)0.7095 (3)0.0417 (7)
H43A0.29100.00300.78520.050*
C440.5268 (3)0.00251 (12)0.8483 (3)0.0460 (7)
H44A0.46600.00120.91290.055*
C450.6056 (4)0.04741 (14)0.8565 (3)0.0651 (10)
H45A0.54660.07670.84840.078*
H45B0.65610.04870.78430.078*
C460.6968 (4)0.05254 (17)0.9822 (4)0.0845 (13)
H46A0.74920.08360.97950.101*
H46B0.64680.05561.05440.101*
C470.7842 (4)0.00538 (18)1.0010 (4)0.0784 (12)
H47A0.83840.00370.93180.094*
H47B0.84050.00831.08250.094*
C480.7029 (3)0.04415 (14)1.0013 (3)0.0602 (9)
H48A0.65140.04291.07260.072*
H48B0.76020.07401.01400.072*
C490.6135 (3)0.05031 (12)0.8744 (3)0.0441 (7)
H49A0.66700.05390.80380.053*
C500.5933 (3)0.15180 (12)0.6684 (3)0.0465 (7)
C510.4966 (3)0.12880 (13)0.5829 (3)0.0562 (9)
H51A0.42700.11240.61420.067*
C520.5036 (3)0.13026 (12)0.4533 (3)0.0572 (9)
H52A0.43910.11420.39710.069*
C530.6054 (3)0.15531 (13)0.4025 (3)0.0571 (9)
C560.6095 (4)0.15820 (17)0.2584 (4)0.0808 (12)
H56A0.56000.13010.21660.121*
H56B0.69790.15570.24100.121*
H56C0.57330.19060.22600.121*
C540.7014 (4)0.17739 (15)0.4897 (4)0.0667 (10)
H54A0.77060.19410.45870.080*
C550.6973 (3)0.17529 (14)0.6205 (4)0.0619 (9)
H55B0.76430.18960.67720.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0363 (4)0.0466 (5)0.0653 (5)0.0005 (4)0.0010 (3)0.0134 (4)
S20.0368 (4)0.0521 (5)0.0641 (5)0.0009 (4)0.0024 (4)0.0160 (4)
O10.0394 (12)0.0753 (16)0.0429 (13)0.0017 (11)0.0049 (10)0.0054 (11)
O20.0485 (13)0.0521 (14)0.0887 (18)0.0055 (11)0.0090 (13)0.0206 (12)
O30.0440 (12)0.0625 (16)0.0764 (16)0.0099 (11)0.0051 (11)0.0178 (12)
O40.0415 (12)0.0774 (17)0.0407 (12)0.0045 (11)0.0058 (10)0.0053 (11)
O50.0462 (13)0.0517 (14)0.0903 (18)0.0060 (10)0.0108 (12)0.0237 (12)
O60.0416 (13)0.0784 (18)0.0746 (17)0.0114 (12)0.0065 (12)0.0147 (13)
N10.0471 (15)0.0451 (15)0.0368 (14)0.0050 (12)0.0031 (12)0.0030 (11)
N20.0363 (14)0.0494 (15)0.0532 (16)0.0010 (11)0.0095 (12)0.0073 (12)
N30.0499 (15)0.0450 (15)0.0332 (13)0.0024 (12)0.0011 (11)0.0015 (11)
N40.0357 (14)0.0532 (16)0.0558 (17)0.0023 (12)0.0112 (12)0.0057 (12)
C10.0435 (17)0.0359 (16)0.0394 (17)0.0038 (13)0.0065 (13)0.0016 (13)
C60.0452 (17)0.0394 (16)0.0384 (17)0.0022 (13)0.0055 (14)0.0043 (13)
C110.058 (2)0.0478 (18)0.0331 (17)0.0068 (15)0.0099 (15)0.0057 (14)
C140.079 (2)0.056 (2)0.052 (2)0.0010 (18)0.0240 (19)0.0016 (16)
C120.096 (3)0.063 (2)0.061 (2)0.026 (2)0.022 (2)0.0090 (17)
C130.080 (3)0.092 (3)0.039 (2)0.002 (2)0.0022 (19)0.0076 (18)
C50.0507 (19)0.0474 (18)0.0388 (17)0.0019 (14)0.0019 (14)0.0020 (13)
C40.0438 (17)0.0572 (19)0.0418 (18)0.0043 (14)0.0066 (14)0.0051 (14)
C70.0435 (19)0.096 (3)0.052 (2)0.0048 (19)0.0003 (16)0.012 (2)
C80.062 (5)0.120 (8)0.153 (11)0.037 (5)0.003 (6)0.022 (8)
C90.068 (6)0.22 (2)0.065 (6)0.019 (9)0.025 (4)0.020 (8)
C100.038 (5)0.122 (8)0.085 (6)0.016 (5)0.017 (4)0.031 (6)
C9'0.075 (11)0.108 (14)0.30 (5)0.029 (9)0.031 (17)0.07 (2)
C11'0.030 (7)0.22 (3)0.22 (3)0.024 (12)0.043 (12)0.11 (2)
C10'0.063 (11)0.33 (5)0.22 (3)0.03 (2)0.012 (15)0.18 (4)
C30.0489 (18)0.061 (2)0.0339 (16)0.0021 (15)0.0126 (14)0.0005 (14)
C20.0453 (17)0.0381 (16)0.0380 (17)0.0025 (13)0.0042 (13)0.0006 (13)
C150.0537 (19)0.0456 (18)0.0317 (17)0.0005 (15)0.0067 (14)0.0061 (13)
C160.0458 (18)0.0502 (18)0.0312 (17)0.0010 (14)0.0050 (14)0.0022 (13)
C170.072 (2)0.050 (2)0.051 (2)0.0014 (17)0.0022 (18)0.0002 (16)
C180.070 (2)0.066 (2)0.061 (2)0.0103 (19)0.0034 (19)0.0070 (18)
C190.048 (2)0.074 (2)0.054 (2)0.0076 (18)0.0077 (17)0.0013 (18)
C200.0451 (17)0.063 (2)0.0460 (18)0.0020 (16)0.0036 (15)0.0072 (15)
C210.0334 (15)0.0510 (18)0.0409 (17)0.0027 (13)0.0040 (13)0.0086 (13)
C220.0360 (15)0.0349 (16)0.065 (2)0.0026 (14)0.0046 (14)0.0021 (15)
C230.0415 (18)0.076 (3)0.081 (3)0.0112 (17)0.0072 (18)0.013 (2)
C240.052 (2)0.083 (3)0.087 (3)0.0130 (19)0.026 (2)0.007 (2)
C250.069 (2)0.0467 (19)0.066 (2)0.0021 (19)0.0150 (18)0.0020 (17)
C280.101 (3)0.086 (3)0.076 (3)0.016 (3)0.024 (2)0.007 (2)
C260.058 (2)0.052 (2)0.063 (2)0.0067 (16)0.0020 (18)0.0050 (16)
C270.0438 (18)0.055 (2)0.065 (2)0.0095 (15)0.0066 (17)0.0055 (16)
C290.0415 (16)0.0391 (16)0.0360 (16)0.0002 (13)0.0059 (13)0.0005 (12)
C340.0482 (17)0.0420 (17)0.0300 (15)0.0048 (13)0.0065 (13)0.0004 (12)
C390.0511 (18)0.056 (2)0.0359 (17)0.0052 (16)0.0091 (14)0.0007 (14)
C420.083 (3)0.080 (3)0.054 (2)0.006 (2)0.025 (2)0.0034 (19)
C400.088 (3)0.072 (3)0.053 (2)0.023 (2)0.014 (2)0.0115 (17)
C410.078 (2)0.105 (3)0.0347 (19)0.015 (2)0.0072 (18)0.0123 (19)
C330.0435 (16)0.0413 (17)0.0391 (17)0.0018 (13)0.0030 (13)0.0016 (13)
C320.0462 (17)0.0445 (17)0.0418 (18)0.0028 (14)0.0112 (15)0.0055 (14)
C350.0392 (16)0.054 (2)0.057 (2)0.0060 (15)0.0119 (15)0.0111 (16)
C360.055 (4)0.067 (5)0.118 (7)0.011 (3)0.018 (4)0.007 (4)
C370.048 (5)0.068 (5)0.136 (11)0.017 (4)0.019 (6)0.011 (4)
C380.048 (4)0.204 (16)0.061 (5)0.005 (6)0.026 (3)0.030 (6)
C36'0.044 (7)0.093 (11)0.26 (3)0.002 (7)0.035 (11)0.033 (14)
C37'0.036 (7)0.36 (5)0.098 (15)0.034 (18)0.021 (9)0.09 (2)
C38'0.054 (7)0.138 (16)0.160 (16)0.027 (8)0.029 (8)0.044 (12)
C310.0484 (18)0.0528 (19)0.0343 (17)0.0032 (15)0.0109 (14)0.0045 (13)
C300.0429 (16)0.0403 (16)0.0347 (15)0.0025 (13)0.0029 (13)0.0035 (12)
C430.0470 (18)0.0421 (17)0.0375 (18)0.0000 (14)0.0106 (14)0.0014 (13)
C440.0504 (18)0.0566 (19)0.0301 (15)0.0046 (15)0.0019 (13)0.0008 (13)
C450.079 (2)0.061 (2)0.051 (2)0.0168 (19)0.0068 (19)0.0011 (16)
C460.096 (3)0.089 (3)0.063 (3)0.034 (3)0.015 (2)0.012 (2)
C470.060 (2)0.112 (4)0.059 (2)0.032 (2)0.0091 (19)0.006 (2)
C480.0456 (18)0.082 (3)0.050 (2)0.0018 (18)0.0049 (16)0.0044 (17)
C490.0389 (15)0.0540 (19)0.0393 (17)0.0085 (14)0.0048 (13)0.0025 (14)
C500.0380 (15)0.0366 (16)0.064 (2)0.0059 (15)0.0043 (15)0.0039 (15)
C510.0469 (18)0.052 (2)0.066 (2)0.0078 (15)0.0040 (17)0.0070 (16)
C520.060 (2)0.051 (2)0.056 (2)0.0075 (16)0.0080 (18)0.0048 (16)
C530.063 (2)0.0436 (19)0.066 (2)0.0089 (17)0.0131 (18)0.0031 (17)
C560.088 (3)0.079 (3)0.078 (3)0.005 (2)0.020 (2)0.006 (2)
C540.054 (2)0.065 (2)0.084 (3)0.0067 (18)0.023 (2)0.003 (2)
C550.0429 (19)0.062 (2)0.081 (3)0.0047 (16)0.0079 (18)0.0157 (19)
Geometric parameters (Å, º) top
S1—O31.426 (2)C24—C251.385 (5)
S1—O21.441 (2)C24—H24A0.9300
S1—N21.610 (3)C25—C261.373 (5)
S1—C221.759 (3)C25—C281.505 (5)
S2—O61.426 (2)C28—H28A0.9600
S2—O51.441 (2)C28—H28B0.9600
S2—N41.608 (3)C28—H28C0.9600
S2—C501.767 (3)C26—C271.380 (5)
O1—C11.354 (3)C26—H26A0.9300
O1—H10.8200C27—H27A0.9300
O4—C291.357 (3)C29—C301.404 (4)
O4—H4A0.8200C29—C341.408 (4)
N1—C151.274 (4)C34—C331.390 (4)
N1—C161.471 (4)C34—C391.543 (4)
N2—C211.477 (4)C39—C411.528 (4)
N2—H2B0.8600C39—C401.529 (5)
N3—C431.265 (4)C39—C421.534 (5)
N3—C441.464 (4)C42—H42A0.9600
N4—C491.483 (4)C42—H42B0.9600
N4—H4B0.8600C42—H42C0.9600
C1—C21.396 (4)C40—H40A0.9600
C1—C61.415 (4)C40—H40B0.9600
C6—C51.379 (4)C40—H40C0.9600
C6—C111.538 (4)C41—H41A0.9600
C11—C141.518 (4)C41—H41B0.9600
C11—C121.532 (4)C41—H41C0.9600
C11—C131.535 (4)C33—C321.399 (4)
C14—H14A0.9600C33—H33A0.9300
C14—H14B0.9600C32—C311.366 (4)
C14—H14C0.9600C32—C351.546 (4)
C12—H12A0.9600C35—C37'1.424 (17)
C12—H12B0.9600C35—C36'1.458 (15)
C12—H12C0.9600C35—C381.469 (7)
C13—H13A0.9600C35—C371.517 (10)
C13—H13B0.9600C35—C361.580 (8)
C13—H13C0.9600C35—C38'1.641 (14)
C5—C41.400 (4)C36—H36A0.9600
C5—H5B0.9300C36—H36B0.9600
C4—C31.382 (4)C36—H36C0.9600
C4—C71.535 (4)C37—H37A0.9600
C7—C10'1.47 (3)C37—H37B0.9600
C7—C91.508 (12)C37—H37C0.9600
C7—C9'1.548 (19)C38—H38A0.9600
C7—C101.563 (13)C38—H38B0.9600
C7—C81.570 (12)C38—H38C0.9600
C7—C11'1.59 (2)C36'—H36D0.9600
C8—H8A0.9600C36'—H36E0.9600
C8—H8B0.9600C36'—H36F0.9600
C8—H8C0.9600C37'—H37D0.9600
C9—H9A0.9600C37'—H37E0.9600
C9—H9B0.9600C37'—H37F0.9600
C9—H9C0.9600C38'—H38D0.9600
C10—H10A0.9600C38'—H38E0.9600
C10—H10B0.9600C38'—H38F0.9600
C10—H10C0.9600C31—C301.401 (4)
C9'—H9'A0.9600C31—H31A0.9300
C9'—H9'B0.9600C30—C431.460 (4)
C9'—H9'C0.9600C43—H43A0.9300
C11'—H11A0.9600C44—C491.530 (4)
C11'—H11B0.9600C44—C451.521 (4)
C11'—H11C0.9600C44—H44A0.9800
C10'—H10D0.9600C45—C461.522 (5)
C10'—H10E0.9600C45—H45A0.9700
C10'—H10F0.9600C45—H45B0.9700
C3—C21.397 (4)C46—C471.515 (6)
C3—H3C0.9300C46—H46A0.9700
C2—C151.458 (4)C46—H46B0.9700
C15—H15A0.9300C47—C481.531 (5)
C16—C211.530 (4)C47—H47A0.9700
C16—C171.537 (4)C47—H47B0.9700
C16—H16A0.9800C48—C491.524 (4)
C17—C181.518 (4)C48—H48A0.9700
C17—H17A0.9700C48—H48B0.9700
C17—H17B0.9700C49—H49A0.9800
C18—C191.522 (5)C50—C511.388 (4)
C18—H18A0.9700C50—C551.385 (5)
C18—H18B0.9700C51—C521.362 (5)
C19—C201.505 (5)C51—H51A0.9300
C19—H19A0.9700C52—C531.398 (5)
C19—H19B0.9700C52—H52A0.9300
C20—C211.536 (4)C53—C541.384 (5)
C20—H20A0.9700C53—C561.508 (5)
C20—H20B0.9700C56—H56A0.9600
C21—H21A0.9800C56—H56B0.9600
C22—C231.363 (4)C56—H56C0.9600
C22—C271.385 (4)C54—C551.369 (5)
C23—C241.396 (5)C54—H54A0.9300
C23—H23A0.9300C55—H55B0.9300
O3—S1—O2118.76 (13)H28A—C28—H28B109.5
O3—S1—N2109.09 (14)C25—C28—H28C109.5
O2—S1—N2106.00 (13)H28A—C28—H28C109.5
O3—S1—C22107.31 (14)H28B—C28—H28C109.5
O2—S1—C22108.15 (14)C25—C26—C27122.1 (3)
N2—S1—C22106.99 (14)C25—C26—H26A118.9
O6—S2—O5118.66 (14)C27—C26—H26A118.9
O6—S2—N4108.97 (15)C26—C27—C22119.5 (3)
O5—S2—N4105.89 (14)C26—C27—H27A120.2
O6—S2—C50107.67 (14)C22—C27—H27A120.2
O5—S2—C50107.28 (14)O4—C29—C30119.9 (2)
N4—S2—C50107.95 (14)O4—C29—C34120.1 (2)
C1—O1—H1109.5C30—C29—C34120.1 (3)
C29—O4—H4A109.5C33—C34—C29116.9 (3)
C15—N1—C16119.4 (3)C33—C34—C39121.8 (3)
C21—N2—S1119.41 (19)C29—C34—C39121.3 (3)
C21—N2—H2B120.3C41—C39—C40107.5 (3)
S1—N2—H2B120.3C41—C39—C42107.3 (3)
C43—N3—C44118.7 (3)C40—C39—C42109.8 (3)
C49—N4—S2121.58 (19)C41—C39—C34112.3 (2)
C49—N4—H4B119.2C40—C39—C34110.0 (3)
S2—N4—H4B119.2C42—C39—C34109.9 (3)
O1—C1—C2120.2 (3)C39—C42—H42A109.5
O1—C1—C6119.5 (2)C39—C42—H42B109.5
C2—C1—C6120.3 (3)H42A—C42—H42B109.5
C5—C6—C1116.2 (3)C39—C42—H42C109.5
C5—C6—C11122.3 (3)H42A—C42—H42C109.5
C1—C6—C11121.4 (3)H42B—C42—H42C109.5
C14—C11—C12109.8 (3)C39—C40—H40A109.5
C14—C11—C13107.5 (3)C39—C40—H40B109.5
C12—C11—C13107.4 (3)H40A—C40—H40B109.5
C14—C11—C6110.9 (2)C39—C40—H40C109.5
C12—C11—C6110.0 (3)H40A—C40—H40C109.5
C13—C11—C6111.2 (3)H40B—C40—H40C109.5
C11—C14—H14A109.5C39—C41—H41A109.5
C11—C14—H14B109.5C39—C41—H41B109.5
H14A—C14—H14B109.5H41A—C41—H41B109.5
C11—C14—H14C109.5C39—C41—H41C109.5
H14A—C14—H14C109.5H41A—C41—H41C109.5
H14B—C14—H14C109.5H41B—C41—H41C109.5
C11—C12—H12A109.5C34—C33—C32124.6 (3)
C11—C12—H12B109.5C34—C33—H33A117.7
H12A—C12—H12B109.5C32—C33—H33A117.7
C11—C12—H12C109.5C31—C32—C33116.5 (3)
H12A—C12—H12C109.5C31—C32—C35122.3 (3)
H12B—C12—H12C109.5C33—C32—C35121.2 (3)
C11—C13—H13A109.5C37'—C35—C36'118.8 (14)
C11—C13—H13B109.5C37'—C35—C38129.3 (9)
H13A—C13—H13B109.5C36'—C35—C3852.9 (9)
C11—C13—H13C109.5C36'—C35—C37141.6 (7)
H13A—C13—H13C109.5C38—C35—C37111.1 (7)
H13B—C13—H13C109.5C37'—C35—C32114.9 (8)
C6—C5—C4125.7 (3)C36'—C35—C32108.5 (5)
C6—C5—H5B117.1C38—C35—C32114.4 (4)
C4—C5—H5B117.1C37—C35—C32109.8 (5)
C3—C4—C5116.0 (3)C37'—C35—C3667.5 (15)
C3—C4—C7122.7 (3)C36'—C35—C3659.1 (10)
C5—C4—C7121.3 (3)C38—C35—C36107.3 (6)
C10'—C7—C9123.4 (15)C37—C35—C36105.7 (5)
C10'—C7—C4119.3 (10)C32—C35—C36108.1 (3)
C9—C7—C4113.7 (6)C37'—C35—C38'104.3 (15)
C10'—C7—C9'108.6 (14)C36'—C35—C38'106.6 (12)
C9—C7—C9'69.4 (14)C38—C35—C38'53.7 (8)
C4—C7—C9'108.8 (7)C37—C35—C38'67.5 (8)
C9—C7—C10111.9 (8)C32—C35—C38'102.0 (6)
C4—C7—C10107.8 (5)C36—C35—C38'149.5 (6)
C9'—C7—C10138.5 (11)C35—C36—H36A109.5
C10'—C7—C872 (2)C35—C36—H36B109.5
C9—C7—C8109.5 (7)C35—C36—H36C109.5
C4—C7—C8107.8 (5)C35—C37—H37A109.5
C10—C7—C8105.7 (7)C35—C37—H37B109.5
C10'—C7—C11'107 (2)C35—C37—H37C109.5
C4—C7—C11'107.1 (7)C35—C38—H38A109.5
C9'—C7—C11'105.2 (14)C35—C38—H38B109.5
C10—C7—C11'81.7 (18)C35—C38—H38C109.5
C8—C7—C11'139.7 (10)C35—C36'—H36D109.5
C7—C8—H8A109.5C35—C36'—H36E109.5
C7—C8—H8B109.5H36D—C36'—H36E109.5
C7—C8—H8C109.5C35—C36'—H36F109.5
C7—C9—H9A109.5H36D—C36'—H36F109.5
C7—C9—H9B109.4H36E—C36'—H36F109.5
C7—C9—H9C109.5C35—C37'—H37D109.5
C7—C10—H10A109.5C35—C37'—H37E109.5
C7—C10—H10B109.5H37D—C37'—H37E109.5
C7—C10—H10C109.5C35—C37'—H37F109.5
C7—C9'—H9'A109.4H37D—C37'—H37F109.5
C7—C9'—H9'B109.5H37E—C37'—H37F109.5
H9'A—C9'—H9'B109.5C35—C38'—H38D109.5
C7—C9'—H9'C109.5C35—C38'—H38E109.5
H9'A—C9'—H9'C109.5H38D—C38'—H38E109.5
H9'B—C9'—H9'C109.5C35—C38'—H38F109.5
C7—C11'—H11A109.5H38D—C38'—H38F109.5
C7—C11'—H11B109.4H38E—C38'—H38F109.5
H11A—C11'—H11B109.5C32—C31—C30122.4 (3)
C7—C11'—H11C109.4C32—C31—H31A118.8
H11A—C11'—H11C109.5C30—C31—H31A118.8
H11B—C11'—H11C109.5C31—C30—C29119.5 (3)
C7—C10'—H10D109.4C31—C30—C43118.9 (3)
C7—C10'—H10E109.5C29—C30—C43121.5 (3)
H10D—C10'—H10E109.5N3—C43—C30123.6 (3)
C7—C10'—H10F109.5N3—C43—H43A118.2
H10D—C10'—H10F109.5C30—C43—H43A118.2
H10E—C10'—H10F109.5N3—C44—C49111.0 (2)
C4—C3—C2121.6 (3)N3—C44—C45107.8 (2)
C4—C3—H3C119.2C49—C44—C45111.7 (3)
C2—C3—H3C119.2N3—C44—H44A108.7
C3—C2—C1120.2 (3)C49—C44—H44A108.7
C3—C2—C15117.9 (3)C45—C44—H44A108.7
C1—C2—C15121.8 (3)C46—C45—C44113.2 (3)
N1—C15—C2123.5 (3)C46—C45—H45A108.9
N1—C15—H15A118.3C44—C45—H45A108.9
C2—C15—H15A118.3C46—C45—H45B108.9
N1—C16—C21110.7 (2)C44—C45—H45B108.9
N1—C16—C17107.8 (2)H45A—C45—H45B107.8
C21—C16—C17111.0 (2)C45—C46—C47109.8 (3)
N1—C16—H16A109.1C45—C46—H46A109.7
C21—C16—H16A109.1C47—C46—H46A109.7
C17—C16—H16A109.1C45—C46—H46B109.7
C18—C17—C16113.7 (3)C47—C46—H46B109.7
C18—C17—H17A108.8H46A—C46—H46B108.2
C16—C17—H17A108.8C46—C47—C48110.4 (3)
C18—C17—H17B108.8C46—C47—H47A109.6
C16—C17—H17B108.8C48—C47—H47A109.6
H17A—C17—H17B107.7C46—C47—H47B109.6
C17—C18—C19110.3 (3)C48—C47—H47B109.6
C17—C18—H18A109.6H47A—C47—H47B108.1
C19—C18—H18A109.6C49—C48—C47111.2 (3)
C17—C18—H18B109.6C49—C48—H48A109.4
C19—C18—H18B109.6C47—C48—H48A109.4
H18A—C18—H18B108.1C49—C48—H48B109.4
C20—C19—C18109.9 (3)C47—C48—H48B109.4
C20—C19—H19A109.7H48A—C48—H48B108.0
C18—C19—H19A109.7N4—C49—C48110.6 (2)
C20—C19—H19B109.7N4—C49—C44109.9 (2)
C18—C19—H19B109.7C48—C49—C44110.6 (3)
H19A—C19—H19B108.2N4—C49—H49A108.6
C19—C20—C21111.6 (3)C48—C49—H49A108.6
C19—C20—H20A109.3C44—C49—H49A108.6
C21—C20—H20A109.3C51—C50—C55119.4 (3)
C19—C20—H20B109.3C51—C50—S2120.8 (2)
C21—C20—H20B109.3C55—C50—S2119.8 (3)
H20A—C20—H20B108.0C52—C51—C50119.9 (3)
N2—C21—C16109.8 (2)C52—C51—H51A120.1
N2—C21—C20110.4 (2)C50—C51—H51A120.1
C16—C21—C20110.0 (2)C51—C52—C53121.7 (3)
N2—C21—H21A108.9C51—C52—H52A119.1
C16—C21—H21A108.9C53—C52—H52A119.1
C20—C21—H21A108.9C54—C53—C52117.3 (3)
C23—C22—C27120.0 (3)C54—C53—C56121.6 (3)
C23—C22—S1120.0 (2)C52—C53—C56121.1 (3)
C27—C22—S1120.0 (2)C53—C56—H56A109.5
C22—C23—C24119.4 (3)C53—C56—H56B109.5
C22—C23—H23A120.3H56A—C56—H56B109.5
C24—C23—H23A120.3C53—C56—H56C109.5
C25—C24—C23121.7 (3)H56A—C56—H56C109.5
C25—C24—H24A119.2H56B—C56—H56C109.5
C23—C24—H24A119.2C55—C54—C53121.7 (3)
C26—C25—C24117.2 (3)C55—C54—H54A119.1
C26—C25—C28121.8 (3)C53—C54—H54A119.1
C24—C25—C28120.9 (3)C54—C55—C50120.0 (3)
C25—C28—H28A109.5C54—C55—H55B120.0
C25—C28—H28B109.5C50—C55—H55B120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.892.621 (3)149
O4—H4A···N30.821.882.619 (3)149
N2—H2B···O5i0.862.362.987 (3)130
N4—H4B···O2ii0.862.302.950 (3)133
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC28H40N2O3S
Mr484.68
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)10.3873 (10), 25.773 (2), 10.4127 (10)
β (°) 97.269 (2)
V3)2765.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.15
Crystal size (mm)0.35 × 0.30 × 0.21
Data collection
DiffractometerBruker SMART 1K CCD
diffractometer
Absorption correctionMulti-scan
(MULscanABS in SADABS; Sheldrick, 2002)
Tmin, Tmax0.950, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
15079, 9696, 7043
Rint0.034
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.119, 0.97
No. of reflections9696
No. of parameters689
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.25
Absolute structureFlack (1983), 4173 Friedel pairs
Absolute structure parameter0.04 (6)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2003) and local programs.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.892.621 (3)148.9
O4—H4A···N30.821.882.619 (3)149.0
N2—H2B···O5i0.862.362.987 (3)130.1
N4—H4B···O2ii0.862.302.950 (3)132.9
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1.
 

Acknowledgements

We are grateful for the financial support of the National Science Foundation of China (grant No. 20601011) and the Science Foundation of Gansu Province of China (grant No. 0803RJZA103).

References

First citationBalsells, J., Mejorado, L., Phillips, M., Ortega, F., Aguirre, G., Somanathan, R. & Walsh, P. J. (1998). Tetrahedron Asymmetry, 9, 4135–4142.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationEndo, M., Aida, T. & Inoue, S. (1987). Macromolecules, 20, 2982–2988.  CrossRef CAS Web of Science Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602–626.  Web of Science CrossRef CAS Google Scholar

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