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The human tachykinin NK-2 (hNK-2) receptor is considered a promising target for relevant pathologies at the respiratory, gastrointestinal and genitourinary level. With the aim of reducing the complexity of existing peptide antagonists, two series of hNK-2 receptor antagonists were designed, with the support of modelling, and synthesized. The X-ray structure determination of two compounds, each belonging to one of the two series, allowed the experimental validation of the initial rationale. In addition, it has been found that the two series share a β-turn structure, a key feature for binding the hNK-2 receptor.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106018167/gp5007sup1.cif
Contains datablocks 1, 2, publication_text

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106018167/gp50071sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106018167/gp50072sup3.hkl
Contains datablock 2

CCDC references: 289379; 289380

Computing details top

For both compounds, data collection: SMART, Siemens (1995); cell refinement: SMART, Siemens (1995); data reduction: SAINT, Siemens (1995); program(s) used to solve structure: Sir97 (Altomare, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farruggia, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
(1) top
Crystal data top
C45H67N9O11SDx = 1.285 Mg m3
Mr = 942.14Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 3800 reflections
a = 11.359 (3) Åθ = 3.1–56.5°
b = 18.383 (4) ŵ = 1.15 mm1
c = 23.325 (7) ÅT = 298 K
V = 4871 (2) Å3Prism, colourless
Z = 40.6 × 0.4 × 0.3 mm
F(000) = 2016
Data collection top
Three circles SMART CCD
diffractometer
5411 independent reflections
Radiation source: Siemens rotating anode4612 reflections with I > 2σ(I)
Goebel mirrors monochromatorRint = 0.037
intensity from ω scansθmax = 56.5°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements)
SADABS (Sheldrick, 1996)
h = 127
Tmin = 0.564, Tmax = 0.705k = 1912
8834 measured reflectionsl = 2525
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0854P)2 + 0.3813P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5411 reflectionsΔρmax = 0.54 e Å3
597 parametersΔρmin = 0.35 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (3)
Crystal data top
C45H67N9O11SV = 4871 (2) Å3
Mr = 942.14Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 11.359 (3) ŵ = 1.15 mm1
b = 18.383 (4) ÅT = 298 K
c = 23.325 (7) Å0.6 × 0.4 × 0.3 mm
Data collection top
Three circles SMART CCD
diffractometer
5411 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS (Sheldrick, 1996)
4612 reflections with I > 2σ(I)
Tmin = 0.564, Tmax = 0.705Rint = 0.037
8834 measured reflectionsθmax = 56.5°
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.138Δρmax = 0.54 e Å3
S = 1.03Δρmin = 0.35 e Å3
5411 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
597 parametersAbsolute structure parameter: 0.03 (3)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.69273 (13)0.10513 (7)0.27153 (5)0.0339 (4)
O10.7809 (3)0.01736 (15)0.00995 (12)0.0204 (8)
O21.0981 (3)0.01100 (15)0.01490 (13)0.0230 (8)
O31.0793 (3)0.22205 (17)0.06180 (13)0.0247 (8)
O40.7482 (3)0.11762 (16)0.10775 (13)0.0259 (8)
O50.3563 (3)0.09819 (17)0.02467 (13)0.0257 (8)
O60.7170 (4)0.18159 (19)0.27598 (14)0.0469 (11)
O70.6489 (3)0.0668 (2)0.31994 (15)0.0412 (10)
O80.7018 (4)0.0859 (2)0.22300 (16)0.0590 (12)
O90.6356 (4)0.40678 (19)0.11140 (13)0.0441 (11)
O100.7970 (4)0.2084 (2)0.27295 (17)0.0634 (13)
O110.7823 (4)0.2393 (2)0.38700 (15)0.0567 (12)
N10.8322 (3)0.06926 (19)0.05323 (15)0.0194 (9)
H1N0.81310.09370.08320.033 (2)*
N21.0138 (3)0.02870 (18)0.06694 (14)0.0180 (9)
H2N0.95920.02090.09170.033 (2)*
N30.9391 (3)0.1553 (2)0.01689 (15)0.0192 (9)
H3N0.91430.11240.00840.033 (2)*
N40.6836 (3)0.18180 (19)0.03169 (14)0.0160 (9)
H4N0.62830.18610.00670.033 (2)*
N50.5405 (3)0.06757 (19)0.00241 (14)0.0187 (9)
H5N0.58680.06240.03130.033 (2)*
N60.4796 (4)0.0619 (2)0.11437 (14)0.0209 (9)
N70.5901 (4)0.0961 (2)0.22131 (14)0.0233 (10)
N80.8117 (4)0.0636 (3)0.25356 (17)0.0387 (12)
N90.8127 (4)0.3092 (2)0.07344 (15)0.0254 (10)
H9N0.76380.33550.09240.033 (2)*
C10.5904 (4)0.0655 (2)0.05525 (16)0.0181 (11)
H10.52540.07230.08240.033 (2)*
C20.6447 (4)0.0086 (2)0.06741 (18)0.0171 (11)
H2A0.66120.01280.10810.033 (2)*
H2B0.58930.04650.05710.033 (2)*
C30.7590 (4)0.0187 (2)0.03334 (19)0.0197 (11)
C40.9437 (4)0.0839 (2)0.02532 (19)0.0196 (11)
H40.92760.09790.01440.033 (2)*
C51.0233 (4)0.0185 (2)0.02445 (19)0.0172 (11)
C61.0875 (4)0.0928 (2)0.07569 (17)0.0170 (11)
H61.16300.08460.05640.033 (2)*
C71.0332 (4)0.1617 (3)0.05122 (18)0.0188 (11)
C80.8776 (4)0.2173 (2)0.00652 (18)0.0208 (11)
H80.93220.25850.00800.033 (2)*
C90.7743 (4)0.2376 (2)0.03233 (19)0.0212 (11)
H9A0.74090.28340.01960.033 (2)*
H9B0.80260.24420.07120.033 (2)*
C100.6792 (4)0.1247 (2)0.06652 (18)0.0172 (11)
C110.4242 (4)0.0773 (2)0.01201 (19)0.0162 (11)
C120.3845 (4)0.0604 (3)0.07233 (18)0.0197 (11)
H12A0.32490.09530.08360.033 (2)*
H12B0.34850.01250.07280.033 (2)*
C130.5080 (5)0.1366 (2)0.13063 (19)0.0242 (12)
H13A0.44140.15790.15050.033 (2)*
H13B0.52250.16510.09630.033 (2)*
C140.6156 (5)0.1397 (3)0.16910 (19)0.0286 (13)
H14A0.68350.11990.14920.033 (2)*
H14B0.63270.18960.17950.033 (2)*
C150.5602 (5)0.0204 (3)0.20661 (19)0.0282 (13)
H15A0.54240.00660.24130.033 (2)*
H15B0.62660.00260.18790.033 (2)*
C160.4518 (5)0.0194 (3)0.16605 (19)0.0280 (13)
H16A0.43290.03030.15550.033 (2)*
H16B0.38420.04030.18540.033 (2)*
C171.0053 (4)0.1488 (2)0.05539 (19)0.0212 (12)
H17A1.01740.13680.09540.033 (2)*
H17B1.08210.15600.03810.033 (2)*
C180.9377 (4)0.2180 (2)0.05173 (19)0.0195 (11)
C190.8621 (5)0.2450 (3)0.0918 (2)0.0266 (13)
H190.84610.22300.12680.033 (2)*
C200.8552 (4)0.3239 (2)0.01947 (19)0.0223 (12)
C210.8315 (4)0.3827 (2)0.01675 (19)0.0232 (12)
H210.77960.41950.00610.033 (2)*
C220.8878 (5)0.3838 (3)0.0685 (2)0.0314 (14)
H220.87260.42190.09370.033 (2)*
C230.9689 (5)0.3289 (3)0.0850 (2)0.0293 (13)
H231.00720.33210.12010.033 (2)*
C240.9912 (5)0.2706 (3)0.0490 (2)0.0252 (12)
H241.04300.23400.05990.033 (2)*
C250.9331 (4)0.2676 (2)0.00514 (19)0.0202 (11)
C261.1113 (5)0.1032 (3)0.14008 (18)0.0269 (13)
H26A1.03750.09910.16070.033 (2)*
H26B1.14160.15190.14630.033 (2)*
C271.1984 (5)0.0484 (3)0.16453 (17)0.0241 (12)
C281.1668 (5)0.0224 (3)0.17850 (18)0.0254 (12)
H281.08930.03740.17370.033 (2)*
C291.2487 (6)0.0705 (3)0.1993 (2)0.0356 (14)
H291.22630.11810.20700.033 (2)*
C301.3615 (6)0.0498 (3)0.2089 (2)0.0369 (14)
H301.41530.08220.22480.033 (2)*
C311.3952 (5)0.0199 (3)0.1948 (2)0.0400 (15)
H311.47310.03420.19980.033 (2)*
C321.3130 (5)0.0695 (3)0.17294 (19)0.0341 (14)
H321.33610.11670.16410.033 (2)*
C330.8379 (4)0.1997 (3)0.06795 (18)0.0249 (12)
H33A0.79080.23970.08250.033 (2)*
H33B0.78880.15650.06740.033 (2)*
C340.9402 (4)0.1873 (3)0.10712 (19)0.0214 (11)
C350.9838 (5)0.1176 (3)0.11616 (19)0.0269 (13)
H350.94550.07770.10020.033 (2)*
C361.0860 (5)0.1074 (3)0.1495 (2)0.0342 (14)
H361.11740.06110.15440.033 (2)*
C371.1384 (5)0.1664 (3)0.1746 (2)0.0332 (14)
H371.20430.15940.19760.033 (2)*
C381.0956 (5)0.2360 (3)0.1665 (2)0.0331 (14)
H381.13310.27570.18320.033 (2)*
C390.9952 (5)0.2459 (3)0.13289 (19)0.0277 (13)
H390.96490.29240.12780.033 (2)*
C400.5752 (8)0.3331 (3)0.1919 (2)0.071 (2)
H40A0.58930.28990.16990.033 (2)*
H40B0.51300.32420.21890.033 (2)*
H40C0.64560.34630.21220.033 (2)*
C410.5397 (6)0.3947 (3)0.1522 (2)0.0559 (18)
H41A0.46810.38200.13180.033 (2)*
H41B0.52520.43860.17410.033 (2)*
C421.0066 (6)0.1863 (3)0.2715 (2)0.0539 (18)
H42A1.07880.20120.25350.081*
H42B1.01160.19490.31200.081*
H42C0.99380.13550.26460.081*
C430.9092 (7)0.2280 (4)0.2477 (3)0.079 (2)
H43A0.90570.22000.20670.094*
H43B0.92350.27940.25410.094*
C440.8697 (6)0.1249 (3)0.4124 (2)0.0529 (18)
H44A0.87270.08800.44140.079*
H44B0.84270.10390.37700.079*
H44C0.94690.14500.40690.079*
C450.7878 (5)0.1832 (3)0.4304 (2)0.0425 (15)
H45A0.81440.20410.46630.051*
H45B0.71000.16290.43640.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0458 (9)0.0353 (8)0.0206 (6)0.0071 (7)0.0042 (7)0.0016 (6)
O10.0331 (19)0.0078 (16)0.0203 (16)0.0018 (15)0.0011 (16)0.0077 (14)
O20.0346 (19)0.0086 (17)0.0258 (17)0.0018 (16)0.0019 (18)0.0026 (14)
O30.0261 (19)0.0113 (18)0.0366 (19)0.0059 (16)0.0062 (17)0.0021 (15)
O40.039 (2)0.0162 (18)0.0224 (17)0.0020 (17)0.0063 (18)0.0029 (14)
O50.0253 (18)0.029 (2)0.0233 (16)0.0086 (17)0.0041 (17)0.0000 (16)
O60.073 (3)0.031 (2)0.037 (2)0.005 (2)0.017 (2)0.0189 (17)
O70.045 (2)0.041 (2)0.037 (2)0.006 (2)0.001 (2)0.0061 (18)
O80.082 (3)0.047 (3)0.048 (2)0.002 (3)0.001 (3)0.011 (2)
O90.072 (3)0.035 (2)0.0252 (17)0.026 (2)0.010 (2)0.0097 (17)
O100.070 (3)0.070 (3)0.049 (2)0.006 (3)0.000 (3)0.012 (2)
O110.073 (3)0.055 (3)0.043 (2)0.012 (2)0.000 (2)0.004 (2)
N10.030 (2)0.009 (2)0.0192 (19)0.005 (2)0.0007 (19)0.0023 (17)
N20.025 (2)0.009 (2)0.0192 (19)0.0053 (19)0.0015 (19)0.0006 (17)
N30.025 (2)0.009 (2)0.024 (2)0.0028 (19)0.002 (2)0.0009 (17)
N40.017 (2)0.016 (2)0.0156 (18)0.0012 (19)0.0032 (18)0.0019 (16)
N50.027 (2)0.018 (2)0.0118 (19)0.000 (2)0.0099 (18)0.0016 (17)
N60.034 (2)0.015 (2)0.0135 (19)0.005 (2)0.004 (2)0.0012 (17)
N70.039 (2)0.020 (2)0.0113 (18)0.010 (2)0.0099 (19)0.0092 (17)
N80.031 (3)0.050 (3)0.036 (2)0.006 (3)0.013 (2)0.005 (2)
N90.036 (3)0.015 (2)0.026 (2)0.004 (2)0.001 (2)0.0024 (18)
C10.029 (3)0.020 (3)0.005 (2)0.002 (2)0.005 (2)0.001 (2)
C20.024 (3)0.008 (2)0.020 (2)0.003 (2)0.002 (2)0.0027 (19)
C30.030 (3)0.006 (3)0.023 (3)0.003 (3)0.012 (2)0.005 (2)
C40.027 (3)0.008 (3)0.024 (2)0.006 (2)0.005 (2)0.000 (2)
C50.030 (3)0.003 (2)0.019 (2)0.006 (2)0.002 (3)0.001 (2)
C60.023 (3)0.010 (3)0.018 (2)0.008 (2)0.006 (2)0.003 (2)
C70.019 (3)0.021 (3)0.016 (2)0.002 (3)0.001 (2)0.014 (2)
C80.030 (3)0.012 (2)0.021 (2)0.001 (2)0.003 (2)0.000 (2)
C90.024 (3)0.012 (3)0.027 (3)0.007 (2)0.008 (2)0.007 (2)
C100.022 (3)0.017 (3)0.013 (2)0.003 (2)0.005 (2)0.002 (2)
C110.026 (3)0.005 (2)0.018 (2)0.002 (2)0.009 (3)0.004 (2)
C120.023 (3)0.014 (3)0.022 (2)0.001 (2)0.004 (2)0.003 (2)
C130.040 (3)0.012 (3)0.020 (2)0.002 (3)0.001 (3)0.006 (2)
C140.043 (3)0.022 (3)0.021 (2)0.000 (3)0.007 (3)0.003 (2)
C150.040 (3)0.027 (3)0.017 (2)0.004 (3)0.004 (3)0.007 (2)
C160.039 (3)0.020 (3)0.025 (3)0.004 (3)0.003 (3)0.005 (2)
C170.034 (3)0.009 (3)0.021 (2)0.001 (2)0.007 (3)0.003 (2)
C180.026 (3)0.005 (2)0.028 (3)0.001 (2)0.001 (3)0.009 (2)
C190.045 (3)0.011 (3)0.024 (3)0.001 (3)0.008 (3)0.007 (2)
C200.030 (3)0.011 (3)0.026 (3)0.001 (2)0.001 (2)0.003 (2)
C210.024 (3)0.016 (3)0.030 (3)0.008 (2)0.007 (3)0.004 (2)
C220.039 (3)0.018 (3)0.037 (3)0.015 (3)0.020 (3)0.013 (2)
C230.039 (3)0.026 (3)0.024 (3)0.011 (3)0.001 (3)0.000 (2)
C240.032 (3)0.013 (3)0.031 (3)0.005 (3)0.002 (3)0.004 (2)
C250.029 (3)0.006 (3)0.026 (3)0.004 (2)0.005 (3)0.001 (2)
C260.040 (3)0.023 (3)0.018 (2)0.012 (3)0.002 (2)0.003 (2)
C270.035 (3)0.029 (3)0.009 (2)0.000 (3)0.001 (3)0.003 (2)
C280.034 (3)0.026 (3)0.017 (2)0.005 (3)0.001 (2)0.005 (2)
C290.062 (4)0.022 (3)0.023 (3)0.003 (3)0.004 (3)0.007 (2)
C300.047 (4)0.041 (4)0.023 (3)0.005 (3)0.003 (3)0.008 (3)
C310.029 (3)0.066 (5)0.024 (3)0.006 (3)0.007 (3)0.005 (3)
C320.045 (4)0.037 (3)0.021 (3)0.019 (3)0.000 (3)0.012 (2)
C330.032 (3)0.020 (3)0.023 (2)0.004 (2)0.013 (3)0.001 (2)
C340.021 (3)0.020 (3)0.023 (2)0.001 (2)0.003 (2)0.006 (2)
C350.040 (3)0.018 (3)0.023 (2)0.003 (3)0.008 (3)0.006 (2)
C360.045 (4)0.028 (3)0.030 (3)0.014 (3)0.004 (3)0.002 (3)
C370.031 (3)0.047 (4)0.021 (3)0.012 (3)0.009 (3)0.011 (3)
C380.044 (4)0.030 (3)0.026 (3)0.008 (3)0.009 (3)0.001 (2)
C390.042 (3)0.015 (3)0.026 (3)0.007 (3)0.004 (3)0.000 (2)
C400.134 (7)0.045 (4)0.035 (3)0.004 (5)0.002 (4)0.000 (3)
C410.077 (5)0.046 (4)0.045 (3)0.016 (4)0.017 (4)0.008 (3)
C420.064 (5)0.054 (4)0.043 (3)0.023 (4)0.012 (4)0.010 (3)
C430.085 (6)0.056 (5)0.095 (5)0.001 (5)0.017 (5)0.050 (4)
C440.083 (5)0.029 (3)0.047 (3)0.003 (4)0.009 (4)0.001 (3)
C450.038 (4)0.035 (3)0.054 (4)0.004 (3)0.016 (3)0.003 (3)
Geometric parameters (Å, º) top
S1—O71.421 (4)C6—C71.520 (6)
S1—O61.436 (4)C6—C261.538 (6)
S1—N81.608 (5)C8—C91.529 (6)
S1—N71.661 (4)C8—C331.537 (6)
O1—C31.233 (5)C11—C121.510 (6)
O2—C51.258 (5)C13—C141.517 (7)
O3—C71.251 (5)C15—C161.552 (7)
O4—C101.247 (5)C17—C181.489 (6)
O5—C111.214 (5)C18—C191.362 (7)
O9—C411.462 (7)C18—C251.419 (6)
O10—C431.449 (8)C20—C211.399 (6)
O11—C451.446 (6)C20—C251.402 (6)
N1—C31.331 (6)C21—C221.366 (7)
N1—C41.449 (6)C22—C231.420 (7)
N2—C51.321 (5)C23—C241.386 (7)
N2—C61.460 (5)C24—C251.425 (7)
N3—C71.341 (6)C26—C271.524 (7)
N3—C81.444 (6)C27—C321.372 (7)
N4—C101.328 (5)C27—C281.389 (7)
N4—C91.455 (6)C28—C291.372 (7)
N5—C111.352 (6)C29—C301.355 (8)
N5—C11.460 (5)C30—C311.379 (8)
N6—C121.459 (6)C31—C321.400 (8)
N6—C131.462 (6)C33—C341.496 (6)
N6—C161.470 (6)C34—C391.382 (7)
N7—C151.472 (6)C34—C351.390 (6)
N7—C141.486 (6)C35—C361.411 (7)
N9—C201.375 (6)C36—C371.368 (7)
N9—C191.375 (6)C37—C381.383 (7)
C1—C101.507 (6)C38—C391.396 (7)
C1—C21.522 (6)C40—C411.517 (8)
C2—C31.533 (6)C42—C431.455 (9)
C4—C51.505 (6)C44—C451.480 (8)
C4—C171.551 (6)
O7—S1—O6119.7 (2)O5—C11—N5123.1 (4)
O7—S1—N8105.4 (2)O5—C11—C12122.2 (4)
O6—S1—N8108.8 (3)N5—C11—C12114.7 (4)
O7—S1—N7105.4 (2)N6—C12—C11113.7 (4)
O6—S1—N7106.5 (2)N6—C13—C14111.5 (4)
N8—S1—N7111.0 (2)N7—C14—C13107.9 (4)
C3—N1—C4121.3 (4)N7—C15—C16109.7 (4)
C5—N2—C6126.0 (4)N6—C16—C15108.9 (4)
C7—N3—C8122.8 (4)C18—C17—C4113.5 (4)
C10—N4—C9125.3 (4)C19—C18—C25105.6 (4)
C11—N5—C1122.4 (4)C19—C18—C17126.6 (4)
C12—N6—C13110.8 (3)C25—C18—C17127.7 (4)
C12—N6—C16112.5 (4)C18—C19—N9110.8 (4)
C13—N6—C16109.5 (3)N9—C20—C21129.6 (4)
C15—N7—C14111.3 (3)N9—C20—C25107.1 (4)
C15—N7—S1114.9 (3)C21—C20—C25123.3 (4)
C14—N7—S1112.8 (3)C22—C21—C20117.1 (5)
C20—N9—C19108.1 (4)C21—C22—C23122.2 (4)
N5—C1—C10113.7 (4)C24—C23—C22120.3 (5)
N5—C1—C2110.6 (4)C23—C24—C25118.8 (5)
C10—C1—C2110.0 (4)C20—C25—C18108.3 (4)
C1—C2—C3110.8 (4)C20—C25—C24118.4 (4)
O1—C3—N1122.3 (4)C18—C25—C24133.3 (4)
O1—C3—C2122.0 (4)C27—C26—C6113.4 (4)
N1—C3—C2115.7 (4)C32—C27—C28118.4 (5)
N1—C4—C5112.5 (4)C32—C27—C26118.9 (5)
N1—C4—C17109.5 (4)C28—C27—C26122.7 (5)
C5—C4—C17110.5 (4)C29—C28—C27120.8 (5)
O2—C5—N2122.1 (4)C30—C29—C28121.3 (5)
O2—C5—C4120.2 (4)C29—C30—C31118.9 (6)
N2—C5—C4117.7 (4)C30—C31—C32120.5 (5)
N2—C6—C7112.8 (4)C27—C32—C31120.1 (5)
N2—C6—C26109.7 (4)C34—C33—C8111.9 (4)
C7—C6—C26109.5 (4)C39—C34—C35119.4 (5)
O3—C7—N3122.0 (4)C39—C34—C33119.9 (4)
O3—C7—C6119.6 (4)C35—C34—C33120.6 (4)
N3—C7—C6118.3 (4)C34—C35—C36120.0 (5)
N3—C8—C9109.9 (4)C37—C36—C35119.2 (5)
N3—C8—C33109.2 (4)C36—C37—C38121.5 (5)
C9—C8—C33112.3 (4)C37—C38—C39119.0 (5)
N4—C9—C8111.4 (3)C34—C39—C38120.9 (5)
O4—C10—N4122.1 (4)O9—C41—C40108.3 (5)
O4—C10—C1118.6 (4)O10—C43—C42112.6 (5)
N4—C10—C1119.3 (4)O11—C45—C44110.2 (5)
(2) top
Crystal data top
C37H48N4O4SF(000) = 1384
Mr = 644.85Dx = 1.218 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 14.0346 (8) ÅCell parameters from 4501 reflections
b = 9.8834 (7) Åθ = 1.7–57.1°
c = 25.617 (2) ŵ = 1.16 mm1
β = 98.152 (3)°T = 298 K
V = 3517.4 (4) Å3Parallelepipedon, pale yellow
Z = 40.4 × 0.4 × 0.3 mm
Data collection top
Three circles SMART CCD
diffractometer
7090 independent reflections
Radiation source: Siemens rotating anode5160 reflections with I > 2σ(I)
Goebel mirrors monochromatorRint = 0.043
intensity from ω scansθmax = 57.1°, θmin = 1.7°
Absorption correction: empirical (using intensity measurements)
SADABS (Sheldrick, 1996)
h = 1515
Tmin = 0.665, Tmax = 0.705k = 1010
13267 measured reflectionsl = 2426
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.187 w = 1/[σ2(Fo2) + (0.1097P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
7090 reflectionsΔρmax = 0.27 e Å3
831 parametersΔρmin = 0.18 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (3)
Crystal data top
C37H48N4O4SV = 3517.4 (4) Å3
Mr = 644.85Z = 4
Monoclinic, P21Cu Kα radiation
a = 14.0346 (8) ŵ = 1.16 mm1
b = 9.8834 (7) ÅT = 298 K
c = 25.617 (2) Å0.4 × 0.4 × 0.3 mm
β = 98.152 (3)°
Data collection top
Three circles SMART CCD
diffractometer
7090 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS (Sheldrick, 1996)
5160 reflections with I > 2σ(I)
Tmin = 0.665, Tmax = 0.705Rint = 0.043
13267 measured reflectionsθmax = 57.1°
Refinement top
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.187Δρmax = 0.27 e Å3
S = 1.07Δρmin = 0.18 e Å3
7090 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
831 parametersAbsolute structure parameter: 0.07 (3)
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*/Ueq
C1A0.7889 (7)0.3336 (11)0.8004 (5)0.134 (4)
H1A10.73700.32300.77200.202*
H1A20.79010.42510.81300.202*
H1A30.84880.31330.78810.202*
C2A0.7743 (6)0.2370 (10)0.8452 (5)0.080 (3)
C3A0.7571 (7)0.2879 (11)0.8942 (6)0.108 (4)
H3A0.75340.38090.89900.129*
C4A0.7457 (7)0.2017 (13)0.9355 (5)0.101 (3)
H4A0.73590.23670.96810.121*
C5A0.7489 (5)0.0597 (11)0.9279 (4)0.072 (2)
C6A0.7445 (5)0.0438 (11)0.9662 (4)0.078 (3)
H6A0.73700.02791.00120.093*
C7A0.7524 (4)0.1664 (10)0.9455 (3)0.064 (2)
S1A0.76483 (14)0.1622 (2)0.87898 (9)0.0730 (6)
C8A0.7624 (5)0.0130 (8)0.8781 (4)0.059 (2)
C9A0.7760 (5)0.1006 (10)0.8373 (4)0.078 (3)
H9A0.78630.06630.80470.093*
C10A0.7568 (5)0.3013 (10)0.9708 (4)0.064 (2)
O1A0.7431 (4)0.4048 (6)0.9432 (2)0.0804 (17)
N1A0.7820 (4)0.3076 (8)1.0240 (3)0.0691 (19)
H1A0.77840.23531.04230.083*
C11A0.8153 (5)0.4337 (10)1.0515 (3)0.067 (2)
C12A0.9058 (5)0.4832 (11)1.0315 (4)0.108 (4)
H12A0.90690.45300.99550.129*
H12B0.90850.58121.03220.129*
C13A0.9847 (7)0.428 (2)1.0654 (6)0.190 (7)
H13A1.03780.49181.06920.228*
H13B1.00600.34551.05020.228*
C14A0.9580 (7)0.3997 (15)1.1158 (5)0.136 (5)
H14A0.98630.46581.14140.163*
H14B0.98060.31051.12760.163*
C15A0.8482 (5)0.4060 (12)1.1103 (3)0.098 (3)
H15A0.82760.47811.13180.118*
H15B0.82210.32101.12080.118*
C16A0.7346 (5)0.5372 (10)1.0470 (3)0.063 (2)
O2A0.7587 (3)0.6579 (7)1.0535 (2)0.0844 (17)
N2A0.6433 (3)0.4991 (6)1.0433 (2)0.0508 (15)
H2A0.62870.41581.03640.061*
C17A0.5677 (5)0.5937 (8)1.0504 (3)0.060 (2)
H17A0.59920.67581.06570.073*
C18A0.5044 (5)0.5416 (8)1.0896 (3)0.065 (2)
H18A0.45180.60501.09020.078*
H18B0.47650.45631.07640.078*
C19A0.5515 (7)0.5198 (9)1.1457 (4)0.079 (3)
C20A0.5035 (8)0.4454 (10)1.1798 (5)0.100 (3)
H20A0.44460.40561.16750.120*
C21A0.5429 (12)0.4305 (13)1.2313 (5)0.133 (5)
H21A0.50770.38881.25490.160*
C22A0.6375 (12)0.4785 (13)1.2491 (4)0.129 (5)
H22A0.66690.46051.28320.155*
C23A0.6832 (8)0.5490 (13)1.2164 (4)0.117 (4)
H23A0.74400.58351.22850.141*
C24A0.6421 (6)0.5734 (11)1.1635 (3)0.090 (3)
H24A0.67490.62411.14110.108*
C25A0.5064 (5)0.6357 (9)0.9986 (3)0.060 (2)
O3A0.4629 (4)0.7439 (6)0.9959 (2)0.0787 (16)
N3A0.4981 (5)0.5489 (8)0.9601 (3)0.097 (3)
H3A10.53120.47550.96410.117*
C26A0.4330 (6)0.5713 (11)0.9090 (3)0.099 (3)
H26A0.37790.51150.90770.119*
H26B0.40930.66360.90820.119*
C27A0.4795 (5)0.5479 (8)0.8616 (3)0.068 (2)
H27A0.53600.60690.86360.082*
C28A0.4097 (6)0.5861 (10)0.8123 (3)0.087 (3)
H28A0.35150.53260.81120.104*
H28B0.39220.68060.81450.104*
C29A0.4526 (6)0.5630 (10)0.7621 (3)0.082 (2)
H29A0.40660.58950.73200.098*
H29B0.50980.61830.76250.098*
N4A0.4773 (5)0.4221 (7)0.7576 (3)0.0770 (19)
C30A0.5473 (7)0.3796 (10)0.8038 (4)0.105 (3)
H30A0.60700.42880.80350.126*
H30B0.56110.28400.80060.126*
C31A0.5115 (6)0.4038 (9)0.8549 (4)0.084 (3)
H31A0.56220.38180.88350.101*
H31B0.45780.34360.85750.101*
C32A0.5114 (6)0.3895 (12)0.7092 (3)0.107 (3)
H32A0.54470.30330.71350.128*
H32B0.55830.45730.70260.128*
C33A0.4348 (6)0.3807 (10)0.6604 (3)0.083 (3)
H33A0.40850.47170.65300.099*
C34A0.3537 (7)0.2899 (11)0.6685 (3)0.103 (3)
H34A0.31860.33010.69460.124*
H34B0.37980.20430.68250.124*
C35A0.2849 (7)0.2630 (12)0.6193 (4)0.118 (4)
H35A0.23710.19770.62690.141*
H35B0.25170.34620.60780.141*
O4A0.3336 (4)0.2121 (6)0.5777 (2)0.0906 (18)
C36A0.4007 (7)0.3072 (11)0.5664 (4)0.110 (3)
H36A0.36780.39130.55610.132*
H36B0.43070.27550.53680.132*
C37A0.4775 (7)0.3335 (12)0.6123 (3)0.107 (3)
H37A0.52120.40210.60260.128*
H37B0.51410.25130.62090.128*
C1B0.3317 (7)0.5761 (11)0.2939 (4)0.120 (3)
H1B10.39920.56790.29180.180*
H1B20.31720.66790.30220.180*
H1B30.29540.55140.26070.180*
C2B0.3053 (6)0.4828 (10)0.3367 (4)0.078 (3)
C3B0.2874 (6)0.5345 (10)0.3840 (5)0.089 (3)
H3B0.28910.62780.38880.107*
C4B0.2670 (5)0.4532 (10)0.4244 (4)0.073 (2)
H4B0.25570.49150.45610.087*
C5B0.2632 (4)0.3138 (9)0.4179 (3)0.056 (2)
C6B0.2482 (5)0.2080 (9)0.4547 (3)0.063 (2)
H6B0.23490.22470.48860.075*
C7B0.2553 (4)0.0821 (9)0.4349 (3)0.0556 (19)
S1B0.27749 (13)0.0857 (2)0.36997 (8)0.0678 (6)
C8B0.2818 (4)0.2621 (8)0.3706 (4)0.061 (2)
C9B0.3025 (5)0.3444 (9)0.3289 (3)0.066 (2)
H9B0.31400.30690.29710.079*
C10B0.2528 (5)0.0495 (10)0.4612 (3)0.059 (2)
O1B0.2340 (4)0.1525 (6)0.4353 (2)0.0719 (16)
N1B0.2783 (3)0.0502 (7)0.5142 (2)0.0557 (16)
H1B0.28170.02520.53120.067*
C11B0.3005 (4)0.1776 (8)0.5436 (3)0.057 (2)
C12B0.3903 (5)0.2458 (9)0.5268 (3)0.073 (2)
H12C0.38470.34350.52810.088*
H12D0.39850.21910.49130.088*
C13B0.4707 (7)0.1992 (19)0.5645 (5)0.183 (7)
H13C0.50650.13110.54810.220*
H13D0.51370.27440.57480.220*
C14B0.4370 (7)0.1424 (17)0.6109 (4)0.161 (6)
H14C0.46150.05110.61700.193*
H14D0.46000.19660.64170.193*
C15B0.3288 (5)0.1405 (9)0.6022 (3)0.078 (3)
H15C0.30470.05150.60950.094*
H15D0.30320.20610.62480.094*
C16B0.2141 (5)0.2728 (9)0.5372 (3)0.056 (2)
O2B0.2249 (3)0.3953 (6)0.5377 (2)0.0714 (15)
N2B0.1265 (4)0.2151 (6)0.5345 (2)0.0555 (16)
H2B0.12370.12820.53360.067*
C17B0.0362 (4)0.2890 (7)0.5328 (3)0.056 (2)
H17B0.01330.22250.53820.067*
C18B0.0370 (5)0.3956 (9)0.5763 (3)0.074 (2)
H18C0.02610.43730.57330.089*
H18D0.08290.46570.57070.089*
C19B0.0625 (5)0.3404 (9)0.6311 (4)0.071 (2)
C20B0.1516 (6)0.3583 (10)0.6599 (4)0.095 (3)
H20B0.19870.40340.64450.114*
C21B0.1732 (8)0.3123 (15)0.7100 (5)0.125 (4)
H21B0.23500.32490.72790.151*
C22B0.1075 (12)0.2493 (14)0.7341 (4)0.120 (4)
H22B0.12330.21810.76850.144*
C23B0.0150 (12)0.2308 (11)0.7073 (6)0.127 (4)
H23B0.03240.18870.72340.153*
C24B0.0038 (7)0.2765 (10)0.6564 (5)0.096 (3)
H24B0.06530.26310.63820.115*
C25B0.0030 (5)0.3574 (8)0.4800 (3)0.065 (2)
O3B0.0674 (4)0.4311 (6)0.4752 (2)0.0928 (18)
N3B0.0488 (4)0.3275 (7)0.4392 (3)0.0744 (18)
H3B10.09560.27070.44340.089*
C26B0.0208 (7)0.3896 (10)0.3872 (4)0.096 (3)
H26C0.04660.48080.38800.115*
H26D0.04880.39670.38070.115*
C27B0.0528 (8)0.3175 (10)0.3434 (4)0.112 (3)
H27B0.12330.31540.34760.134*
C28B0.013 (2)0.3929 (15)0.2919 (5)0.364 (19)
H28C0.03550.48570.29370.437*
H28D0.05700.39430.28790.437*
C29B0.0452 (16)0.3232 (14)0.2453 (5)0.255 (11)
H29C0.11490.32000.24990.305*
H29D0.02360.37450.21360.305*
N4B0.0094 (5)0.1952 (9)0.2399 (3)0.090 (2)
C30B0.0447 (9)0.1232 (12)0.2853 (5)0.132 (4)
H30C0.02310.03010.28110.158*
H30D0.11450.12280.28920.158*
C31B0.0139 (8)0.1793 (12)0.3344 (4)0.113 (3)
H31C0.03760.12210.36420.136*
H31D0.05580.18140.33100.136*
C32B0.0271 (8)0.1388 (12)0.1898 (4)0.123 (4)
H32C0.04120.04320.19480.148*
H32D0.08430.18140.18000.148*
C33B0.0497 (8)0.1528 (10)0.1461 (4)0.102 (3)
H33B0.06520.24940.14260.123*
C34B0.0251 (11)0.1050 (14)0.0934 (5)0.155 (5)
H34C0.04450.10060.09660.186*
H34D0.04580.17530.06790.186*
C35B0.0577 (11)0.0065 (19)0.0735 (5)0.237 (11)
H35C0.06500.00410.03550.285*
H35D0.00770.07370.08270.285*
O4B0.1428 (4)0.0624 (8)0.0854 (2)0.108 (2)
C36B0.1675 (9)0.0193 (18)0.1335 (5)0.201 (9)
H36C0.15130.09410.15770.241*
H36D0.23710.01320.12820.241*
C37B0.1401 (10)0.0802 (15)0.1579 (5)0.167 (6)
H37C0.19230.14530.15320.201*
H37D0.12980.05580.19500.201*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.134 (8)0.110 (8)0.146 (11)0.020 (8)0.024 (7)0.032 (9)
C2A0.066 (5)0.056 (6)0.110 (9)0.007 (4)0.018 (5)0.002 (7)
C3A0.095 (7)0.084 (9)0.137 (11)0.011 (6)0.013 (7)0.042 (9)
C4A0.095 (7)0.110 (10)0.095 (9)0.004 (6)0.005 (6)0.040 (8)
C5A0.060 (5)0.086 (7)0.072 (7)0.003 (5)0.017 (4)0.041 (7)
C6A0.063 (5)0.111 (8)0.056 (6)0.021 (5)0.001 (4)0.028 (7)
C7A0.052 (4)0.080 (6)0.054 (6)0.003 (4)0.008 (3)0.026 (6)
S1A0.0840 (13)0.0769 (14)0.0555 (15)0.0005 (12)0.0005 (11)0.0134 (13)
C8A0.042 (4)0.066 (6)0.066 (7)0.009 (4)0.002 (4)0.010 (5)
C9A0.072 (5)0.090 (8)0.069 (7)0.000 (5)0.003 (5)0.021 (6)
C10A0.040 (4)0.086 (7)0.064 (7)0.012 (4)0.000 (4)0.012 (6)
O1A0.104 (4)0.070 (4)0.059 (4)0.006 (3)0.015 (3)0.015 (3)
N1A0.052 (3)0.110 (6)0.043 (5)0.008 (4)0.001 (3)0.017 (4)
C11A0.048 (5)0.109 (7)0.040 (5)0.002 (5)0.010 (4)0.000 (5)
C12A0.038 (4)0.190 (11)0.093 (8)0.022 (6)0.003 (5)0.027 (7)
C13A0.059 (7)0.34 (2)0.163 (13)0.001 (10)0.005 (8)0.092 (15)
C14A0.080 (7)0.207 (13)0.105 (9)0.003 (8)0.039 (6)0.029 (9)
C15A0.073 (5)0.170 (10)0.050 (6)0.036 (6)0.001 (4)0.001 (6)
C16A0.044 (4)0.105 (7)0.036 (5)0.023 (5)0.002 (3)0.008 (5)
O2A0.068 (3)0.099 (5)0.082 (4)0.033 (3)0.003 (3)0.001 (4)
N2A0.043 (3)0.063 (4)0.044 (4)0.007 (3)0.002 (3)0.002 (3)
C17A0.057 (4)0.066 (5)0.054 (5)0.005 (4)0.005 (4)0.003 (5)
C18A0.058 (4)0.081 (6)0.055 (6)0.005 (4)0.007 (4)0.003 (4)
C19A0.080 (6)0.098 (7)0.058 (7)0.022 (5)0.008 (5)0.002 (5)
C20A0.142 (8)0.085 (7)0.085 (9)0.010 (6)0.054 (8)0.007 (7)
C21A0.229 (15)0.124 (10)0.055 (9)0.056 (11)0.048 (9)0.040 (8)
C22A0.224 (15)0.118 (11)0.039 (8)0.086 (11)0.010 (9)0.013 (7)
C23A0.149 (9)0.150 (11)0.047 (7)0.059 (8)0.004 (7)0.007 (7)
C24A0.102 (7)0.127 (8)0.040 (6)0.028 (6)0.008 (5)0.014 (6)
C25A0.062 (4)0.066 (6)0.049 (6)0.004 (4)0.003 (4)0.006 (5)
O3A0.090 (4)0.070 (4)0.068 (4)0.014 (3)0.018 (3)0.001 (3)
N3A0.125 (6)0.100 (6)0.055 (5)0.052 (5)0.031 (4)0.024 (5)
C26A0.099 (6)0.122 (8)0.063 (7)0.036 (6)0.029 (5)0.004 (6)
C27A0.077 (5)0.086 (6)0.039 (5)0.022 (4)0.004 (4)0.004 (5)
C28A0.101 (6)0.099 (6)0.054 (6)0.032 (5)0.010 (5)0.005 (6)
C29A0.079 (5)0.107 (7)0.057 (6)0.018 (5)0.002 (4)0.002 (6)
N4A0.087 (4)0.089 (5)0.051 (5)0.026 (4)0.003 (4)0.010 (4)
C30A0.117 (7)0.124 (9)0.064 (7)0.055 (6)0.023 (6)0.017 (6)
C31A0.094 (6)0.079 (6)0.072 (7)0.021 (5)0.013 (5)0.005 (5)
C32A0.092 (6)0.162 (10)0.059 (7)0.022 (6)0.014 (5)0.024 (7)
C33A0.075 (5)0.105 (7)0.066 (7)0.003 (5)0.002 (5)0.020 (5)
C34A0.126 (8)0.121 (8)0.062 (7)0.024 (7)0.013 (6)0.020 (6)
C35A0.114 (8)0.150 (10)0.095 (9)0.045 (7)0.035 (7)0.039 (8)
O4A0.104 (4)0.110 (5)0.057 (4)0.033 (4)0.009 (3)0.012 (4)
C36A0.122 (8)0.133 (9)0.073 (7)0.042 (7)0.010 (6)0.041 (7)
C37A0.108 (7)0.158 (9)0.057 (7)0.021 (7)0.017 (6)0.041 (7)
C1B0.140 (8)0.097 (7)0.122 (9)0.030 (7)0.011 (7)0.017 (8)
C2B0.071 (5)0.087 (8)0.069 (7)0.018 (5)0.009 (5)0.013 (6)
C3B0.089 (6)0.065 (7)0.103 (9)0.014 (5)0.025 (6)0.002 (7)
C4B0.071 (5)0.076 (7)0.067 (7)0.008 (5)0.006 (5)0.026 (6)
C5B0.044 (4)0.069 (6)0.051 (6)0.007 (4)0.005 (4)0.022 (5)
C6B0.056 (4)0.088 (7)0.043 (5)0.007 (4)0.005 (4)0.014 (5)
C7B0.045 (4)0.072 (6)0.047 (5)0.006 (4)0.006 (3)0.019 (5)
S1B0.0732 (12)0.0742 (14)0.0542 (14)0.0010 (11)0.0025 (10)0.0137 (13)
C8B0.037 (4)0.081 (6)0.062 (6)0.007 (4)0.005 (4)0.016 (5)
C9B0.063 (5)0.079 (7)0.053 (6)0.012 (4)0.004 (4)0.011 (5)
C10B0.043 (4)0.081 (7)0.050 (6)0.002 (4)0.003 (4)0.005 (6)
O1B0.081 (3)0.082 (4)0.048 (4)0.009 (3)0.008 (3)0.012 (3)
N1B0.049 (3)0.068 (4)0.048 (4)0.003 (3)0.003 (3)0.009 (4)
C11B0.042 (4)0.078 (5)0.048 (5)0.014 (4)0.003 (3)0.006 (5)
C12B0.051 (4)0.088 (6)0.077 (6)0.003 (4)0.001 (4)0.010 (5)
C13B0.075 (7)0.35 (2)0.114 (10)0.044 (10)0.005 (7)0.081 (13)
C14B0.088 (7)0.30 (2)0.085 (9)0.007 (9)0.025 (7)0.022 (10)
C15B0.085 (6)0.096 (7)0.047 (6)0.012 (5)0.016 (4)0.013 (5)
C16B0.052 (5)0.070 (6)0.041 (5)0.010 (4)0.006 (4)0.022 (4)
O2B0.074 (3)0.067 (4)0.071 (4)0.017 (3)0.004 (3)0.016 (3)
N2B0.056 (4)0.056 (4)0.052 (4)0.003 (3)0.001 (3)0.011 (3)
C17B0.047 (4)0.065 (5)0.053 (5)0.015 (4)0.006 (4)0.005 (4)
C18B0.074 (5)0.079 (6)0.068 (6)0.016 (4)0.005 (5)0.006 (6)
C19B0.050 (4)0.092 (6)0.071 (7)0.004 (5)0.014 (5)0.037 (6)
C20B0.083 (6)0.124 (8)0.074 (8)0.013 (6)0.001 (5)0.022 (6)
C21B0.126 (9)0.201 (13)0.048 (8)0.017 (10)0.009 (7)0.017 (9)
C22B0.184 (12)0.140 (11)0.032 (7)0.041 (9)0.000 (9)0.013 (7)
C23B0.211 (15)0.098 (9)0.084 (10)0.004 (9)0.061 (10)0.011 (8)
C24B0.093 (7)0.110 (8)0.080 (8)0.002 (6)0.003 (6)0.032 (7)
C25B0.053 (4)0.063 (5)0.074 (7)0.016 (4)0.010 (5)0.006 (5)
O3B0.083 (4)0.099 (4)0.093 (5)0.042 (4)0.001 (3)0.007 (4)
N3B0.072 (4)0.091 (5)0.054 (5)0.026 (4)0.011 (4)0.008 (4)
C26B0.124 (7)0.089 (7)0.064 (7)0.022 (6)0.021 (5)0.008 (6)
C27B0.163 (9)0.077 (7)0.082 (8)0.001 (7)0.022 (7)0.003 (7)
C28B0.88 (5)0.140 (13)0.042 (8)0.26 (2)0.027 (16)0.005 (8)
C29B0.56 (3)0.109 (11)0.077 (10)0.094 (17)0.016 (14)0.026 (10)
N4B0.115 (6)0.091 (6)0.060 (6)0.005 (5)0.005 (5)0.002 (5)
C30B0.197 (12)0.114 (9)0.089 (9)0.032 (8)0.034 (9)0.014 (8)
C31B0.157 (9)0.110 (9)0.065 (8)0.029 (7)0.009 (7)0.014 (7)
C32B0.130 (9)0.160 (11)0.085 (9)0.011 (8)0.034 (8)0.013 (8)
C33B0.142 (9)0.097 (7)0.068 (8)0.032 (7)0.016 (7)0.023 (6)
C34B0.208 (13)0.151 (12)0.126 (11)0.066 (10)0.095 (10)0.041 (10)
C35B0.258 (16)0.33 (2)0.164 (13)0.228 (17)0.164 (13)0.183 (15)
O4B0.095 (4)0.162 (6)0.068 (4)0.046 (4)0.014 (3)0.046 (5)
C36B0.158 (11)0.31 (2)0.157 (13)0.158 (13)0.104 (10)0.159 (14)
C37B0.187 (12)0.202 (14)0.130 (11)0.106 (12)0.083 (10)0.110 (11)
Geometric parameters (Å, º) top
C1A—C2A1.529 (13)C1B—C2B1.518 (12)
C2A—C9A1.365 (12)C2B—C3B1.369 (12)
C2A—C3A1.404 (14)C2B—C9B1.382 (11)
C3A—C4A1.386 (15)C3B—C4B1.374 (12)
C4A—C5A1.418 (14)C4B—C5B1.387 (12)
C5A—C8A1.396 (10)C5B—C8B1.376 (10)
C5A—C6A1.425 (13)C5B—C6B1.442 (11)
C6A—C7A1.334 (12)C6B—C7B1.353 (10)
C7A—C10A1.479 (12)C7B—C10B1.467 (12)
C7A—S1A1.737 (8)C7B—S1B1.735 (7)
S1A—C8A1.732 (8)S1B—C8B1.745 (8)
C8A—C9A1.391 (11)C8B—C9B1.404 (10)
C10A—O1A1.242 (10)C10B—O1B1.222 (9)
C10A—N1A1.361 (10)C10B—N1B1.356 (9)
N1A—C11A1.474 (11)N1B—C11B1.477 (9)
C11A—C12A1.516 (10)C11B—C16B1.524 (10)
C11A—C16A1.518 (11)C11B—C15B1.542 (10)
C11A—C15A1.537 (10)C11B—C12B1.542 (9)
C12A—C13A1.416 (14)C12B—C13B1.451 (12)
C13A—C14A1.422 (14)C13B—C14B1.455 (14)
C14A—C15A1.530 (11)C14B—C15B1.503 (12)
C16A—O2A1.244 (9)C16B—O2B1.220 (8)
C16A—N2A1.326 (8)C16B—N2B1.348 (8)
N2A—C17A1.445 (8)N2B—C17B1.459 (8)
C17A—C18A1.522 (9)C17B—C25B1.524 (10)
C17A—C25A1.532 (10)C17B—C18B1.533 (10)
C18A—C19A1.511 (11)C18B—C19B1.501 (11)
C19A—C20A1.385 (12)C19B—C24B1.364 (12)
C19A—C24A1.394 (12)C19B—C20B1.370 (10)
C20A—C21A1.365 (14)C20B—C21B1.355 (13)
C21A—C22A1.422 (17)C21B—C22B1.335 (15)
C22A—C23A1.323 (15)C22B—C23B1.391 (16)
C23A—C24A1.416 (12)C23B—C24B1.369 (14)
C25A—O3A1.229 (8)C25B—O3B1.220 (8)
C25A—N3A1.300 (10)C25B—N3B1.336 (9)
N3A—C26A1.504 (9)N3B—C26B1.469 (10)
C26A—C27A1.475 (10)C26B—C27B1.453 (12)
C27A—C31A1.511 (11)C27B—C31B1.477 (13)
C27A—C28A1.531 (10)C27B—C28B1.549 (15)
C28A—C29A1.512 (10)C28B—C29B1.503 (19)
C29A—N4A1.444 (11)C29B—N4B1.361 (13)
N4A—C32A1.428 (9)N4B—C30B1.393 (12)
N4A—C30A1.487 (10)N4B—C32B1.453 (12)
C30A—C31A1.487 (11)C30B—C31B1.495 (13)
C32A—C33A1.531 (10)C32B—C33B1.446 (13)
C33A—C34A1.487 (12)C33B—C34B1.515 (13)
C33A—C37A1.518 (11)C33B—C37B1.525 (14)
C34A—C35A1.499 (12)C34B—C35B1.272 (15)
C35A—O4A1.436 (10)C35B—O4B1.389 (11)
O4A—C36A1.390 (10)O4B—C36B1.393 (11)
C36A—C37A1.500 (11)C36B—C37B1.198 (14)
C9A—C2A—C3A119.8 (10)C3B—C2B—C9B119.5 (9)
C9A—C2A—C1A119.8 (11)C3B—C2B—C1B120.4 (10)
C3A—C2A—C1A120.4 (10)C9B—C2B—C1B120.1 (10)
C4A—C3A—C2A121.0 (10)C2B—C3B—C4B122.1 (9)
C3A—C4A—C5A119.6 (11)C3B—C4B—C5B120.0 (9)
C8A—C5A—C4A117.7 (10)C8B—C5B—C4B117.7 (9)
C8A—C5A—C6A114.6 (9)C8B—C5B—C6B111.7 (8)
C4A—C5A—C6A127.6 (10)C4B—C5B—C6B130.4 (9)
C7A—C6A—C5A111.4 (9)C7B—C6B—C5B113.4 (7)
C6A—C7A—C10A130.1 (8)C6B—C7B—C10B129.5 (7)
C6A—C7A—S1A113.2 (8)C6B—C7B—S1B111.9 (7)
C10A—C7A—S1A116.6 (7)C10B—C7B—S1B118.5 (6)
C8A—S1A—C7A91.9 (5)C7B—S1B—C8B91.3 (4)
C9A—C8A—C5A122.2 (8)C5B—C8B—C9B122.7 (8)
C9A—C8A—S1A128.9 (7)C5B—C8B—S1B111.6 (7)
C5A—C8A—S1A108.9 (7)C9B—C8B—S1B125.6 (7)
C2A—C9A—C8A119.7 (9)C2B—C9B—C8B117.9 (9)
O1A—C10A—N1A121.9 (9)O1B—C10B—N1B123.0 (8)
O1A—C10A—C7A120.0 (8)O1B—C10B—C7B120.5 (8)
N1A—C10A—C7A118.0 (8)N1B—C10B—C7B116.4 (8)
C10A—N1A—C11A122.5 (7)C10B—N1B—C11B121.4 (7)
N1A—C11A—C12A109.6 (7)N1B—C11B—C16B111.4 (5)
N1A—C11A—C16A110.6 (6)N1B—C11B—C15B107.4 (6)
C12A—C11A—C16A114.1 (8)C16B—C11B—C15B110.0 (6)
N1A—C11A—C15A110.4 (8)N1B—C11B—C12B110.6 (6)
C12A—C11A—C15A103.8 (6)C16B—C11B—C12B111.7 (6)
C16A—C11A—C15A108.1 (7)C15B—C11B—C12B105.5 (6)
C13A—C12A—C11A106.8 (9)C13B—C12B—C11B105.4 (7)
C12A—C13A—C14A110.4 (9)C12B—C13B—C14B110.7 (8)
C13A—C14A—C15A107.5 (8)C13B—C14B—C15B108.8 (8)
C14A—C15A—C11A104.8 (7)C14B—C15B—C11B104.9 (7)
O2A—C16A—N2A121.5 (8)O2B—C16B—N2B122.0 (7)
O2A—C16A—C11A116.8 (7)O2B—C16B—C11B121.1 (7)
N2A—C16A—C11A121.1 (8)N2B—C16B—C11B116.8 (7)
C16A—N2A—C17A121.8 (7)C16B—N2B—C17B125.0 (6)
N2A—C17A—C18A111.9 (6)N2B—C17B—C25B113.8 (6)
N2A—C17A—C25A113.5 (6)N2B—C17B—C18B113.9 (5)
C18A—C17A—C25A110.7 (5)C25B—C17B—C18B108.0 (6)
C19A—C18A—C17A117.4 (6)C19B—C18B—C17B113.9 (7)
C20A—C19A—C24A119.9 (9)C24B—C19B—C20B115.8 (9)
C20A—C19A—C18A119.3 (9)C24B—C19B—C18B121.7 (7)
C24A—C19A—C18A120.8 (8)C20B—C19B—C18B122.3 (9)
C21A—C20A—C19A120.0 (11)C21B—C20B—C19B122.1 (10)
C20A—C21A—C22A120.3 (12)C22B—C21B—C20B121.2 (11)
C23A—C22A—C21A119.2 (11)C21B—C22B—C23B119.4 (11)
C22A—C23A—C24A121.8 (12)C24B—C23B—C22B117.9 (11)
C19A—C24A—C23A118.5 (9)C19B—C24B—C23B123.6 (10)
O3A—C25A—N3A122.8 (7)O3B—C25B—N3B121.7 (8)
O3A—C25A—C17A119.8 (8)O3B—C25B—C17B119.7 (8)
N3A—C25A—C17A117.2 (7)N3B—C25B—C17B118.4 (6)
C25A—N3A—C26A122.8 (7)C25B—N3B—C26B121.4 (7)
C27A—C26A—N3A114.1 (6)C27B—C26B—N3B115.1 (7)
C26A—C27A—C31A114.5 (8)C26B—C27B—C31B115.2 (10)
C26A—C27A—C28A109.5 (6)C26B—C27B—C28B107.8 (9)
C31A—C27A—C28A107.7 (7)C31B—C27B—C28B103.4 (11)
C29A—C28A—C27A112.3 (7)C29B—C28B—C27B109.9 (11)
N4A—C29A—C28A110.0 (7)N4B—C29B—C28B111.0 (15)
C32A—N4A—C29A113.6 (8)C29B—N4B—C30B107.9 (10)
C32A—N4A—C30A111.2 (6)C29B—N4B—C32B109.9 (10)
C29A—N4A—C30A110.4 (7)C30B—N4B—C32B117.2 (9)
N4A—C30A—C31A112.8 (7)N4B—C30B—C31B113.8 (10)
C30A—C31A—C27A113.2 (8)C27B—C31B—C30B109.2 (10)
N4A—C32A—C33A116.0 (7)C33B—C32B—N4B116.4 (9)
C34A—C33A—C37A109.0 (8)C32B—C33B—C34B114.8 (11)
C34A—C33A—C32A112.6 (8)C32B—C33B—C37B110.6 (10)
C37A—C33A—C32A111.6 (7)C34B—C33B—C37B109.3 (9)
C33A—C34A—C35A113.9 (8)C35B—C34B—C33B120.9 (11)
O4A—C35A—C34A111.6 (8)C34B—C35B—O4B121.9 (12)
C36A—O4A—C35A109.0 (7)C35B—O4B—C36B113.7 (8)
O4A—C36A—C37A112.7 (9)C37B—C36B—O4B127.6 (11)
C36A—C37A—C33A111.6 (8)C36B—C37B—C33B119.8 (10)

Experimental details

(1)(2)
Crystal data
Chemical formulaC45H67N9O11SC37H48N4O4S
Mr942.14644.85
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21
Temperature (K)298298
a, b, c (Å)11.359 (3), 18.383 (4), 23.325 (7)14.0346 (8), 9.8834 (7), 25.617 (2)
α, β, γ (°)90, 90, 9090, 98.152 (3), 90
V3)4871 (2)3517.4 (4)
Z44
Radiation typeCu KαCu Kα
µ (mm1)1.151.16
Crystal size (mm)0.6 × 0.4 × 0.30.4 × 0.4 × 0.3
Data collection
DiffractometerThree circles SMART CCD
diffractometer
Three circles SMART CCD
diffractometer
Absorption correctionEmpirical (using intensity measurements)
SADABS (Sheldrick, 1996)
Empirical (using intensity measurements)
SADABS (Sheldrick, 1996)
Tmin, Tmax0.564, 0.7050.665, 0.705
No. of measured, independent and
observed [I > 2σ(I)] reflections
8834, 5411, 4612 13267, 7090, 5160
Rint0.0370.043
θmax (°)56.557.1
(sin θ/λ)max1)0.5410.544
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.138, 1.03 0.075, 0.187, 1.07
No. of reflections54117090
No. of parameters597831
No. of restraints01
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.350.27, 0.18
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.03 (3)0.07 (3)

Computer programs: SMART, Siemens (1995), SAINT, Siemens (1995), Sir97 (Altomare, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farruggia, 1997), PARST97 (Nardelli, 1997).

 

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