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In this study, we report on the X-ray diffraction analysis of the pentapeptide, Boc-Tyr-D-Ala-Gly-(NMe-Phe)-(Met-O-Me), C35H49N5O9S·1.125H2O. This is a protected intermediate in the solution phase synthesis of metkephamid (LY127,623), Tyr-D-Ala-Gly-NMe-Phe-Met-NH2. The peptide crystallizes in the monoclinic space group C2 with two peptide mol­ecules and three solvent (water) mol­ecules in the asymmetric unit. The peptide has an extended conformation similar to other Met-enkephalins.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020475/om6072sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020475/om6072Isup2.hkl
Contains datablock I

CCDC reference: 180529

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.043
  • wR factor = 0.112
  • Data-to-parameter ratio = 10.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
SHFSU_01 Alert C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.056 Additional refinement cycles may be required. THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5883 PLAT_302 Alert C Anion/Solvent Disorder ....................... 12.00 Perc. PLAT_601 Alert C Structure Contains Solvent Accessible VOIDS of 52.00 A   3 PLAT_731 Alert C Bond Calc 0.88(4), Rep 0.874(18) .... 2.22 s.u-Ratio O2S -H2SB 1.555 1.555 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 65.10 From the CIF: _reflns_number_total 10567 Count of symmetry unique reflns 7221 Completeness (_total/calc) 146.34% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3346 Fraction of Friedel pairs measured 0.463 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
5 Alert Level C = Please check

Comment top

Theoretically, linear peptides can have many different backbone conformations. Early X-ray studies (1983–1987) on enkephalin and its analogues showed only two different backbone conformations: extended and single β-bend. No other conformations were observed until a double β-bend was reported in 1989 (for a review, see Deschamps et al., 1996). Despite the small number of conformations observed in the solid state, most enkephalin analogues can adopt many conformations in solution. To constrain the peptide conformation a number of modifications have been investigated, including the substitution, deletion or addition of natural or artificial amino acids and the formation of highly constrained peptide ring systems. In this study, we report on the X-ray diffraction analysis of the pentapeptide, Boc-Tyr-D-Ala-Gly-NMe-Phe-Met-OMe, a protected intermediate in the solution phase synthesis of metkephamid (LY127,623). Metkephamide (Tyr-D-Ala-Gly-NMe-Phe-Met-NH2) is an analog of methionine-enkephalin that retains high affinity for the delta receptor, and has systemic analgesic activity (Frederickson et al., 1981).

The title compound, (I), crystallizes with two peptide molecules and three water molecules in the asymmetric unit (Fig. 1). Additional disordered water molecules are probably present in the crystal, as evidenced by the diffuse residual electron density and voids large enough to accommodate a water molecule were detected by PLATON (Spek, 2001). The two independent peptides molecules have an extended conformation, although even the main-chain atoms cannot be fully superimposed (Fig 2). The extended conformation observed in this study is similar to that of other Met-enkephalins (Doi et al., 1984; Griffin et al., 1986; Doi et al., 1987).

The peptide molecules form an extensive hydrogen bonded network (Table 1). Pairs of adjacent peptide molecules are linked across the chains by six hydrogen bonds (Fig. 3). These pairs are then linked to adjacent pairs by two hydrogen bonds forming extended ribbons. This pattern of cross-chain hydrogen bonds is typical of enkaphalins with an extended conformation (Karle et al., 1983; Griffin et al., 1986; Doi et al., 1987). Two of the solvent (i.e. water) molecules form hydrogen bonds between adjacent ribbons, the third water molecule (O3S) interacts only with other solvent molecules.

In this study, the X-ray diffraction data was collected using a Bruker SMART 6000 detector and a copper rotating anode. Prior to this, we collected X-ray diffraction data at the Cornell High Energy Synchrotron Source (CHESS). The structure determined from the synchrotron data is identical to that reported here. However, the synchrotron determined structure suffered from an incomplete dataset (due to the experimental set up) and unusually large sigmas for the measured intensities. Because of these problems the structure-solution for the synchrotron data was more difficult and the structure did not refine as well.

Experimental top

The peptide, Boc-Tyr-D-Ala-Gly-NMe-Phe-Met-OMe, was supplied by Research Triangle Institute and was prepared using standard methods of peptide synthesis. Crystals were grown by vapor diffusion of petroleum ether into acetone.

Refinement top

The displacement parameters of the terminal methyl group on the disordered methionine side chain were constrained using the ISOR instruction in SHELXTL (Sheldrick, 1997b). Difference peaks for the H atoms on two of the water molecules were located. The positions of these H atoms were refined with the O—H and H···H distances constrained to reasonable values. [Please explain the additional parts of the molecular formula, i.e.. H2O.0.125O]

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXS97.

Figures top
[Figure 1] Fig. 1. The structure of Boc-Tyr-D-Ala-Gly-NMe-Phe-Met-OMe showing the relationship of the two independent peptide molecules and the associated water molecules. Displacement ellipsoids are shown at the 30% probability level.
[Figure 2] Fig. 2. The conformation of Boc-Tyr-D-Ala-Gly-NMe-Phe-Met-OMe. The two independent peptide molecules are superimposed (alignment was based on the positions of the main-chain N and O atoms). Although the two independent molecules have similar conformations even the main-chain atoms cannot be superimposed. Additional differences are present in the orientations of the side chains.
[Figure 3] Fig. 3. Across-chain hydrogen bonding in Boc-Tyr-D-Ala-Gly-NMe-Phe-Met-OMe. The six hydrogen bonds between the pair of peptide molecules in the asymmetric unit are and the two hydrogen bonds connecting adjacent pairs are shown as dashed lines. Solvent molecules and side chains not involved in hydrogen bonding have been omitted for clarity.
boc-Metkephamid-OMe top
Crystal data top
C35H49N5O9S·H2O·0.125OF(000) = 3144
Mr = 735.87Dx = 1.220 Mg m3
Monoclinic, C2Cu Kα radiation, λ = 1.54178 Å
a = 38.354 (1) ÅCell parameters from 928 reflections
b = 11.000 (1) Åθ = 5.5–124.6°
c = 22.689 (1) ŵ = 1.21 mm1
β = 123.15 (1)°T = 153 K
V = 8014.4 (8) Å3Prism, colorless
Z = 80.52 × 0.50 × 0.46 mm
Data collection top
Bruker SMART 6000 CCD
diffractometer
10567 independent reflections
Radiation source: rotating anode8802 reflections with I > 2σ(I)
Gobel optics monochromatorRint = 0.033
ω scansθmax = 65.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 4244
Tmin = 0.559, Tmax = 0.573k = 1212
17149 measured reflectionsl = 2625
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0576P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112(Δ/σ)max = 0.056
S = 1.01Δρmax = 0.22 e Å3
10567 reflectionsΔρmin = 0.23 e Å3
966 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
11 restraintsExtinction coefficient: 0.000290 (16)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.00 (2)
Crystal data top
C35H49N5O9S·H2O·0.125OV = 8014.4 (8) Å3
Mr = 735.87Z = 8
Monoclinic, C2Cu Kα radiation
a = 38.354 (1) ŵ = 1.21 mm1
b = 11.000 (1) ÅT = 153 K
c = 22.689 (1) Å0.52 × 0.50 × 0.46 mm
β = 123.15 (1)°
Data collection top
Bruker SMART 6000 CCD
diffractometer
10567 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
8802 reflections with I > 2σ(I)
Tmin = 0.559, Tmax = 0.573Rint = 0.033
17149 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112Δρmax = 0.22 e Å3
S = 1.01Δρmin = 0.23 e Å3
10567 reflectionsAbsolute structure: Flack (1983)
966 parametersAbsolute structure parameter: 0.00 (2)
11 restraints
Special details top

Experimental. Final cell refinement and decay correction applied after integration as part of merge process in SAINT v6.02 A.

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)
C10.20958 (8)0.1808 (3)0.67153 (17)0.0599 (8)
C20.17653 (10)0.2765 (3)0.63626 (18)0.0697 (9)
H2A0.15510.26070.64490.105*
H2B0.18860.35490.65480.105*
H2C0.16480.27510.58650.105*
C30.24368 (10)0.2013 (4)0.6584 (2)0.0997 (12)
H3A0.23170.20740.60870.150*
H3B0.25820.27530.68100.150*
H3C0.26280.13440.67720.150*
C40.22749 (10)0.1709 (3)0.74995 (17)0.0797 (12)
H4A0.20530.15940.75710.119*
H4B0.24620.10290.76910.119*
H4C0.24230.24410.77310.119*
C50.16102 (7)0.0091 (2)0.63663 (12)0.0429 (6)
O00.14031 (5)0.05678 (18)0.65617 (10)0.0570 (5)
O0.19344 (5)0.06060 (17)0.63914 (10)0.0520 (5)
N10.15405 (5)0.10180 (19)0.60842 (10)0.0427 (5)
H1A0.16920.12570.59330.051*
C1A0.12238 (6)0.1850 (2)0.60159 (12)0.0397 (6)
H1AA0.10550.14370.61590.048*
C1B0.14382 (7)0.2956 (3)0.64876 (14)0.0517 (7)
H1BA0.16090.26770.69710.062*
H1BB0.16240.33030.63670.062*
C1G0.11589 (7)0.3949 (3)0.64524 (13)0.0459 (6)
C1D10.10570 (7)0.4047 (3)0.69560 (14)0.0502 (7)
H1DA0.11400.34350.72900.060*
C1E10.08386 (8)0.5020 (3)0.69700 (14)0.0538 (7)
H1EA0.07760.50610.73110.065*
C1Z0.07112 (7)0.5943 (3)0.64781 (14)0.0518 (7)
O1Z0.05121 (6)0.6921 (2)0.65272 (11)0.0656 (5)
H1ZA0.05230.74900.63040.098*
C1E20.07910 (8)0.5834 (3)0.59531 (15)0.0553 (7)
H1EB0.06920.64200.56010.066*
C1D20.10167 (8)0.4864 (3)0.59507 (14)0.0521 (7)
H1DB0.10750.48210.56040.062*
C1'0.09493 (6)0.2200 (2)0.52390 (12)0.0366 (5)
O10.11108 (5)0.26260 (18)0.49390 (9)0.0466 (4)
N20.05439 (5)0.19929 (19)0.49064 (9)0.0369 (5)
H2D0.04430.16940.51320.044*
C2A0.02686 (7)0.2271 (2)0.41571 (12)0.0408 (6)
H2AA0.04190.21240.39270.049*
C2B0.01257 (9)0.3586 (3)0.40377 (17)0.0650 (9)
H2BA0.03640.41120.42380.097*
H2BB0.00240.37370.42580.097*
H2BC0.00530.37390.35420.097*
C2'0.01032 (6)0.1425 (2)0.38413 (11)0.0375 (5)
O20.02728 (5)0.11913 (17)0.41595 (8)0.0462 (4)
N30.02403 (6)0.0995 (2)0.32083 (10)0.0485 (6)
H3D0.01070.11530.30120.058*
C3A0.06148 (8)0.0259 (3)0.28388 (13)0.0576 (8)
H3AA0.08140.05630.29400.069*
H3AB0.05470.05720.30080.069*
C3'0.08088 (7)0.0273 (2)0.20562 (12)0.0418 (6)
O30.06220 (5)0.07265 (18)0.18080 (8)0.0488 (5)
N40.11845 (5)0.0263 (2)0.16651 (10)0.0421 (5)
C4N0.14027 (8)0.0751 (3)0.19829 (14)0.0566 (7)
H4NA0.12270.13280.23430.085*
H4NB0.16550.11450.16270.085*
H4NC0.14690.00980.21870.085*
C4A0.13759 (7)0.0420 (3)0.09079 (12)0.0426 (6)
H4AA0.11990.00080.07820.051*
C4B0.14080 (8)0.1754 (3)0.06996 (14)0.0498 (7)
H4BA0.15690.21900.08450.060*
H4BB0.15550.18130.01910.060*
C4G0.09864 (8)0.2339 (3)0.10298 (15)0.0532 (7)
C4D10.07727 (8)0.2767 (3)0.17159 (15)0.0559 (7)
H4DA0.08990.27320.19680.067*
C4E10.03787 (9)0.3242 (3)0.20317 (19)0.0721 (10)
H4EA0.02390.35040.24970.087*
C4Z0.01912 (10)0.3331 (4)0.1665 (2)0.0838 (12)
H4ZA0.00730.36680.18760.101*
C4E20.03971 (10)0.2917 (4)0.0982 (2)0.0873 (11)
H4EB0.02700.29760.07320.105*
C4D20.07948 (10)0.2410 (4)0.06578 (18)0.0727 (9)
H4DB0.09300.21230.01980.087*
C4'0.18029 (7)0.0191 (3)0.05022 (14)0.0490 (7)
O40.21055 (6)0.0231 (2)0.04811 (14)0.0864 (8)
N50.18228 (6)0.1214 (2)0.01828 (11)0.0468 (5)
H5A0.16010.14760.02160.056*
C5A0.22011 (7)0.1912 (3)0.02197 (14)0.0478 (6)
H5AA0.23490.18800.00220.057*
C5B0.20982 (8)0.3234 (3)0.02593 (15)0.0528 (7)
H5BA0.23470.36720.06060.063*
H5BB0.18960.32860.03890.063*
C5G0.19136 (19)0.3783 (7)0.0496 (3)0.0625 (19)0.607 (2)
H5GA0.17680.31490.08450.075*0.607 (2)
H5GB0.21400.40720.05330.075*0.607 (2)
S50.15525 (4)0.50422 (12)0.06840 (7)0.0620 (4)0.607 (2)
C5D0.1079 (2)0.4096 (9)0.0885 (6)0.119 (4)0.607 (2)
H5DA0.08490.46270.10120.178*0.607 (2)
H5DB0.11470.36370.04750.178*0.607 (2)
H5DC0.10030.35500.12670.178*0.607 (2)
C5G'0.1902 (3)0.4046 (13)0.0377 (7)0.078 (4)0.393 (2)
H5GC0.21050.41500.05020.094*0.393 (2)
H5GD0.18650.48370.02300.094*0.393 (2)
S5'0.14488 (9)0.3684 (3)0.11194 (14)0.1068 (11)0.393 (2)
C5D'0.1132 (4)0.4301 (13)0.0774 (6)0.071 (3)0.393 (2)
H5DD0.08410.42390.11340.106*0.393 (2)
H5DE0.12030.51380.06430.106*0.393 (2)
H5DF0.11910.38390.03700.106*0.393 (2)
C5'0.24805 (7)0.1370 (3)0.09479 (13)0.0447 (6)
O50.23548 (6)0.0820 (2)0.12542 (10)0.0634 (6)
O5'0.28756 (5)0.1579 (2)0.12085 (10)0.0607 (6)
C60.31732 (9)0.1037 (4)0.18819 (16)0.0685 (10)
H6A0.34500.12530.20180.103*
H6B0.31430.01680.18460.103*
H6C0.31240.13280.22290.103*
C110.21310 (8)0.3037 (3)0.15058 (16)0.0593 (8)
C120.23658 (11)0.3041 (4)0.22965 (18)0.0845 (12)
H12A0.21720.29900.24390.127*
H12B0.25510.23570.24800.127*
H12C0.25240.37790.24750.127*
C130.18066 (11)0.3998 (3)0.1175 (2)0.0825 (12)
H13A0.16230.39250.13370.124*
H13B0.19370.47830.13010.124*
H13C0.16500.39070.06720.124*
C140.24257 (10)0.3125 (4)0.1256 (2)0.0881 (12)
H14A0.26300.24920.14710.132*
H14B0.22710.30380.07530.132*
H14C0.25620.39020.13860.132*
C150.16552 (7)0.1358 (3)0.13432 (13)0.0458 (7)
O11"0.19436 (6)0.18327 (19)0.12436 (11)0.0593 (5)
O15"0.14846 (6)0.1896 (2)0.15847 (12)0.0658 (6)
N110.15887 (7)0.0206 (2)0.11335 (13)0.0573 (6)
H11A0.17320.00790.09780.069*
C11A0.12971 (7)0.0613 (3)0.11431 (14)0.0471 (6)
H11B0.11200.01640.12550.056*
C11B0.15384 (8)0.1604 (3)0.16950 (15)0.0558 (8)
H11C0.16890.12270.21570.067*
H11D0.17430.19460.16170.067*
C11G0.12814 (8)0.2621 (3)0.17019 (14)0.0526 (7)
C11D0.11808 (9)0.3615 (3)0.12645 (16)0.0603 (8)
H11E0.12710.36320.09590.072*
C11E0.09502 (9)0.4590 (3)0.12637 (17)0.0677 (9)
H11F0.08890.52450.09630.081*
C11Z0.08132 (9)0.4578 (4)0.17132 (19)0.0753 (10)
O11Z0.06014 (8)0.5521 (3)0.17546 (16)0.1056 (9)
H11G0.06260.61200.15650.158*
C11Y0.09007 (10)0.3578 (4)0.21446 (19)0.0783 (10)
H11H0.08030.35560.24400.094*
C11X0.11306 (9)0.2614 (3)0.21410 (16)0.0663 (9)
H11I0.11860.19510.24340.080*
C11'0.10328 (7)0.1163 (3)0.04072 (12)0.0445 (6)
O110.12059 (5)0.16162 (19)0.01381 (10)0.0547 (5)
N120.06212 (6)0.1100 (3)0.00834 (11)0.0610 (7)
H12D0.05130.07920.02960.073*
C12A0.03522 (8)0.1561 (4)0.06392 (14)0.0752 (11)
H12E0.05140.15800.08550.090*
C12B0.01902 (12)0.2821 (5)0.0671 (2)0.1023 (15)
H12F0.04200.33690.04080.153*
H12G0.00240.28140.04730.153*
H12H0.00230.30840.11520.153*
C12'0.00076 (8)0.0665 (4)0.10518 (15)0.0777 (12)
O120.02313 (6)0.0338 (4)0.08436 (12)0.1115 (13)
N130.00695 (7)0.0305 (3)0.16498 (12)0.0633 (7)
H13D0.01120.04870.17470.076*
C13A0.04303 (9)0.0385 (4)0.21522 (15)0.0667 (9)
H13E0.06110.04900.19810.080*
H13F0.03450.11830.22080.080*
C13'0.06648 (7)0.0257 (3)0.28538 (13)0.0462 (6)
O130.04815 (5)0.0965 (2)0.30163 (9)0.0540 (5)
N140.10714 (6)0.0022 (2)0.32794 (10)0.0425 (5)
C14N0.12804 (8)0.0871 (3)0.30748 (14)0.0539 (7)
H14D0.12820.05430.26840.081*
H14E0.11350.16340.29420.081*
H14F0.15620.09940.34650.081*
C14A0.12988 (7)0.0438 (2)0.40005 (12)0.0412 (6)
H14G0.10990.08800.40610.049*
C14B0.14791 (7)0.0593 (3)0.45453 (13)0.0467 (6)
H14H0.16930.10150.45220.056*
H14I0.16070.02520.50140.056*
C14G0.11449 (7)0.1486 (2)0.44152 (13)0.0452 (6)
C14D0.11486 (9)0.2675 (3)0.42242 (18)0.0658 (8)
H14J0.13680.29430.41920.079*
C14E0.08331 (11)0.3480 (3)0.4079 (2)0.0782 (10)
H14K0.08420.42770.39520.094*
C14Z0.05080 (9)0.3103 (3)0.41233 (17)0.0645 (8)
H14L0.02920.36340.40140.077*
C14Y0.05049 (9)0.1939 (3)0.43294 (16)0.0597 (8)
H14M0.02880.16850.43720.072*
C14X0.08194 (8)0.1132 (3)0.44764 (14)0.0536 (7)
H14N0.08120.03440.46180.064*
C14'0.16399 (7)0.1343 (2)0.41393 (12)0.0411 (6)
O140.18350 (5)0.12637 (19)0.38582 (10)0.0574 (5)
N150.17164 (6)0.2185 (2)0.46196 (11)0.0459 (5)
H15A0.15640.21870.47910.055*
C15A0.20394 (7)0.3092 (2)0.48691 (13)0.0439 (6)
H15B0.22600.27640.48210.053*
C15B0.18708 (8)0.4262 (3)0.44207 (14)0.0520 (7)
H15C0.16750.40340.39330.062*
H15D0.17190.47260.45740.062*
C15G0.22023 (8)0.5072 (3)0.44589 (16)0.0603 (8)
H15E0.23560.46070.43100.072*
H15F0.23960.53080.49450.072*
S150.20030 (2)0.64239 (7)0.39285 (4)0.0635 (2)
C15D0.17037 (19)0.5858 (5)0.3073 (2)0.139 (2)
H15G0.15810.65220.27470.208*
H15H0.14870.53470.30280.208*
H15I0.18780.53940.29740.208*
C15'0.22198 (7)0.3297 (2)0.56408 (13)0.0431 (6)
O150.21183 (5)0.2769 (2)0.59850 (10)0.0594 (5)
O15'0.25061 (5)0.41852 (18)0.58982 (9)0.0523 (5)
C160.26957 (8)0.4467 (3)0.66293 (14)0.0561 (7)
H16A0.28950.51080.67610.084*
H16B0.28340.37580.69080.084*
H16C0.24850.47250.67080.084*
O1S0.05487 (6)0.8813 (2)0.57992 (12)0.0665 (6)
H1SA0.0421 (9)0.947 (4)0.5748 (19)0.093*
H1SB0.0802 (10)0.896 (4)0.5936 (19)0.093*
O2S0.06536 (8)0.2403 (3)0.11361 (19)0.1077 (10)
H2SA0.0911 (5)0.221 (4)0.126 (2)0.151*
H2SB0.0487 (9)0.182 (3)0.086 (2)0.151*
O3S0.0078 (4)0.1467 (10)0.0000 (8)0.104 (4)*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0497 (12)0.0451 (16)0.0807 (18)0.0104 (13)0.0328 (12)0.0204 (13)
C20.0739 (18)0.0463 (18)0.076 (2)0.0018 (16)0.0326 (15)0.0068 (14)
C30.0848 (18)0.071 (2)0.167 (3)0.0409 (18)0.0841 (19)0.052 (2)
C40.0688 (18)0.063 (2)0.065 (2)0.0059 (18)0.0102 (15)0.0215 (16)
C50.0362 (10)0.0476 (15)0.0404 (12)0.0053 (11)0.0180 (8)0.0067 (10)
O00.0548 (8)0.0592 (12)0.0664 (10)0.0063 (9)0.0392 (7)0.0179 (8)
O0.0466 (8)0.0464 (11)0.0681 (10)0.0116 (8)0.0347 (7)0.0176 (8)
N10.0376 (8)0.0437 (12)0.0496 (10)0.0066 (9)0.0256 (7)0.0091 (8)
C1A0.0343 (9)0.0418 (14)0.0414 (12)0.0015 (10)0.0196 (8)0.0005 (9)
C1B0.0343 (10)0.0677 (19)0.0426 (13)0.0010 (12)0.0144 (9)0.0086 (12)
C1G0.0350 (10)0.0520 (16)0.0448 (12)0.0059 (11)0.0181 (9)0.0151 (11)
C1D10.0448 (11)0.0553 (17)0.0452 (13)0.0051 (12)0.0213 (10)0.0062 (11)
C1E10.0500 (11)0.0608 (18)0.0564 (14)0.0075 (13)0.0327 (10)0.0105 (12)
C1Z0.0420 (11)0.0509 (16)0.0602 (15)0.0062 (12)0.0264 (10)0.0157 (12)
O1Z0.0664 (9)0.0559 (12)0.0872 (12)0.0055 (10)0.0502 (9)0.0106 (9)
C1E20.0594 (13)0.0518 (16)0.0556 (15)0.0009 (13)0.0321 (11)0.0056 (12)
C1D20.0559 (12)0.0513 (16)0.0526 (13)0.0047 (13)0.0321 (10)0.0114 (11)
C1'0.0333 (9)0.0315 (12)0.0420 (11)0.0001 (10)0.0187 (8)0.0042 (9)
O10.0353 (7)0.0606 (11)0.0455 (8)0.0046 (8)0.0231 (6)0.0047 (7)
N20.0331 (8)0.0415 (11)0.0344 (9)0.0035 (8)0.0174 (7)0.0007 (8)
C2A0.0318 (10)0.0470 (15)0.0366 (12)0.0025 (10)0.0141 (8)0.0033 (10)
C2B0.0523 (15)0.0497 (18)0.0628 (18)0.0027 (14)0.0121 (13)0.0091 (14)
C2'0.0325 (9)0.0419 (13)0.0349 (11)0.0003 (10)0.0164 (8)0.0010 (9)
O20.0436 (7)0.0587 (11)0.0423 (8)0.0123 (8)0.0273 (6)0.0100 (7)
N30.0430 (8)0.0669 (15)0.0392 (10)0.0179 (10)0.0247 (7)0.0105 (9)
C3A0.0526 (12)0.079 (2)0.0433 (13)0.0257 (14)0.0276 (10)0.0108 (12)
C3'0.0384 (10)0.0471 (15)0.0396 (11)0.0024 (11)0.0211 (8)0.0034 (10)
O30.0391 (7)0.0670 (12)0.0404 (8)0.0127 (8)0.0218 (6)0.0029 (7)
N40.0357 (8)0.0506 (13)0.0411 (10)0.0071 (9)0.0217 (7)0.0037 (8)
C4N0.0556 (12)0.0654 (19)0.0572 (14)0.0201 (13)0.0363 (10)0.0117 (12)
C4A0.0339 (9)0.0533 (16)0.0382 (12)0.0036 (11)0.0180 (8)0.0017 (10)
C4B0.0432 (11)0.0580 (17)0.0396 (13)0.0042 (13)0.0173 (9)0.0043 (11)
C4G0.0494 (12)0.0526 (17)0.0612 (15)0.0067 (12)0.0326 (11)0.0112 (12)
C4D10.0526 (13)0.0512 (17)0.0637 (16)0.0039 (13)0.0317 (11)0.0037 (12)
C4E10.0525 (14)0.076 (2)0.081 (2)0.0077 (16)0.0320 (14)0.0068 (16)
C4Z0.0561 (15)0.082 (3)0.109 (3)0.0117 (18)0.0427 (16)0.005 (2)
C4E20.0755 (15)0.103 (3)0.115 (2)0.003 (2)0.0722 (15)0.016 (2)
C4D20.0715 (16)0.087 (3)0.0684 (18)0.0020 (17)0.0439 (13)0.0069 (16)
C4'0.0375 (10)0.0564 (17)0.0468 (13)0.0052 (12)0.0190 (9)0.0000 (11)
O40.0406 (9)0.0968 (17)0.1152 (16)0.0068 (11)0.0384 (10)0.0476 (13)
N50.0334 (8)0.0548 (14)0.0493 (11)0.0028 (10)0.0207 (7)0.0070 (9)
C5A0.0369 (10)0.0542 (16)0.0498 (13)0.0043 (12)0.0221 (9)0.0010 (11)
C5B0.0465 (12)0.0480 (16)0.0565 (15)0.0032 (13)0.0234 (10)0.0024 (12)
C5G0.065 (3)0.063 (4)0.065 (3)0.025 (3)0.039 (2)0.024 (2)
S50.0606 (6)0.0480 (7)0.0737 (7)0.0073 (6)0.0345 (5)0.0152 (5)
C5D0.046 (3)0.125 (7)0.158 (6)0.013 (4)0.038 (4)0.078 (5)
C5G'0.078 (5)0.073 (8)0.111 (7)0.008 (5)0.068 (5)0.014 (6)
S5'0.1018 (18)0.114 (2)0.0623 (15)0.0175 (17)0.0175 (12)0.0227 (14)
C5D'0.067 (4)0.063 (5)0.073 (4)0.004 (4)0.033 (3)0.018 (4)
C5'0.0405 (10)0.0408 (14)0.0488 (13)0.0007 (11)0.0219 (9)0.0038 (11)
O50.0499 (9)0.0799 (15)0.0561 (10)0.0055 (10)0.0263 (8)0.0118 (10)
O5'0.0335 (7)0.0762 (15)0.0610 (11)0.0016 (9)0.0185 (7)0.0080 (10)
C60.0458 (13)0.081 (2)0.0614 (18)0.0051 (16)0.0180 (12)0.0042 (16)
C110.0490 (13)0.0473 (17)0.0641 (17)0.0096 (14)0.0198 (12)0.0007 (13)
C120.0755 (19)0.073 (2)0.068 (2)0.0311 (19)0.0158 (16)0.0032 (18)
C130.0744 (19)0.059 (2)0.091 (2)0.0010 (19)0.0304 (17)0.0123 (18)
C140.0788 (18)0.082 (3)0.112 (3)0.029 (2)0.0580 (17)0.006 (2)
C150.0368 (11)0.0464 (15)0.0462 (13)0.0036 (11)0.0175 (9)0.0030 (10)
O11"0.0555 (9)0.0504 (12)0.0783 (11)0.0111 (9)0.0405 (8)0.0085 (9)
O15"0.0611 (9)0.0633 (13)0.0837 (12)0.0094 (10)0.0464 (9)0.0193 (10)
N110.0538 (10)0.0498 (14)0.0825 (13)0.0127 (11)0.0465 (9)0.0174 (10)
C11A0.0375 (10)0.0481 (16)0.0528 (13)0.0051 (11)0.0229 (9)0.0049 (11)
C11B0.0443 (12)0.0615 (19)0.0473 (14)0.0048 (13)0.0158 (10)0.0076 (12)
C11G0.0444 (12)0.0595 (18)0.0491 (14)0.0002 (13)0.0225 (10)0.0016 (12)
C11D0.0629 (14)0.065 (2)0.0602 (16)0.0065 (15)0.0380 (12)0.0010 (13)
C11E0.0648 (14)0.069 (2)0.0765 (18)0.0105 (16)0.0435 (13)0.0003 (15)
C11Z0.0582 (14)0.080 (2)0.092 (2)0.0024 (17)0.0444 (14)0.0161 (18)
O11Z0.0949 (12)0.102 (2)0.153 (2)0.0208 (15)0.0891 (13)0.0091 (16)
C11Y0.0799 (16)0.094 (3)0.0863 (19)0.0083 (19)0.0616 (14)0.0134 (17)
C11X0.0670 (15)0.074 (2)0.0597 (17)0.0124 (16)0.0357 (13)0.0021 (14)
C11'0.0415 (10)0.0485 (16)0.0442 (12)0.0053 (11)0.0240 (9)0.0019 (10)
O110.0467 (8)0.0674 (13)0.0580 (10)0.0051 (9)0.0337 (7)0.0091 (8)
N120.0372 (9)0.108 (2)0.0385 (11)0.0071 (12)0.0212 (8)0.0045 (11)
C12A0.0474 (12)0.144 (4)0.0367 (14)0.0155 (18)0.0250 (10)0.0124 (16)
C12B0.083 (2)0.151 (4)0.060 (2)0.044 (3)0.0307 (16)0.032 (2)
C12'0.0366 (11)0.157 (4)0.0412 (14)0.0136 (18)0.0222 (10)0.0093 (17)
O120.0549 (10)0.237 (4)0.0574 (12)0.0148 (17)0.0399 (9)0.0069 (16)
N130.0428 (9)0.109 (2)0.0407 (11)0.0111 (13)0.0248 (8)0.0140 (12)
C13A0.0538 (13)0.092 (2)0.0517 (15)0.0052 (16)0.0268 (11)0.0191 (15)
C13'0.0425 (10)0.0571 (17)0.0433 (12)0.0070 (12)0.0262 (9)0.0032 (11)
O130.0408 (7)0.0745 (14)0.0451 (9)0.0034 (9)0.0224 (6)0.0067 (8)
N140.0412 (8)0.0475 (13)0.0427 (10)0.0018 (9)0.0254 (7)0.0006 (8)
C14N0.0532 (12)0.0547 (17)0.0584 (15)0.0005 (13)0.0334 (11)0.0098 (12)
C14A0.0430 (10)0.0413 (14)0.0407 (12)0.0020 (11)0.0238 (9)0.0015 (10)
C14B0.0413 (10)0.0494 (16)0.0469 (13)0.0015 (12)0.0224 (9)0.0060 (11)
C14G0.0455 (11)0.0435 (15)0.0457 (13)0.0023 (11)0.0244 (9)0.0070 (10)
C14D0.0701 (14)0.0474 (18)0.097 (2)0.0023 (14)0.0565 (14)0.0001 (14)
C14E0.0955 (19)0.0431 (18)0.114 (2)0.0129 (17)0.0689 (17)0.0102 (16)
C14Z0.0637 (14)0.0531 (18)0.0814 (18)0.0157 (15)0.0427 (13)0.0020 (14)
C14Y0.0564 (13)0.0614 (19)0.0716 (16)0.0046 (14)0.0417 (12)0.0035 (13)
C14X0.0581 (13)0.0508 (17)0.0591 (15)0.0022 (13)0.0367 (11)0.0029 (12)
C14'0.0349 (9)0.0452 (14)0.0418 (12)0.0001 (11)0.0201 (8)0.0014 (10)
O140.0564 (8)0.0612 (12)0.0707 (10)0.0118 (9)0.0451 (7)0.0164 (9)
N150.0473 (9)0.0459 (13)0.0530 (11)0.0085 (10)0.0328 (8)0.0032 (9)
C15A0.0408 (10)0.0451 (15)0.0467 (13)0.0059 (11)0.0246 (9)0.0045 (10)
C15B0.0427 (11)0.0565 (17)0.0531 (14)0.0012 (13)0.0239 (10)0.0033 (12)
C15G0.0521 (13)0.064 (2)0.0593 (16)0.0097 (14)0.0270 (11)0.0063 (14)
S150.0647 (4)0.0525 (4)0.0719 (4)0.0033 (4)0.0365 (3)0.0092 (3)
C15D0.220 (6)0.080 (3)0.070 (3)0.023 (4)0.049 (3)0.016 (2)
C15'0.0361 (10)0.0425 (14)0.0504 (13)0.0001 (11)0.0233 (9)0.0013 (10)
O150.0495 (8)0.0762 (14)0.0557 (10)0.0175 (10)0.0309 (7)0.0015 (9)
O15'0.0577 (9)0.0495 (11)0.0489 (9)0.0131 (9)0.0287 (7)0.0058 (8)
C160.0556 (13)0.0618 (19)0.0480 (14)0.0112 (14)0.0265 (11)0.0100 (12)
O1S0.0653 (10)0.0568 (13)0.0840 (12)0.0022 (10)0.0449 (9)0.0121 (10)
O2S0.0823 (13)0.0830 (19)0.172 (2)0.0008 (15)0.0784 (15)0.0180 (17)
Geometric parameters (Å, º) top
C1—O1.474 (3)C6—H6C0.9600
C1—C21.499 (4)C11—O11"1.469 (4)
C1—C31.508 (5)C11—C131.486 (5)
C1—C41.521 (5)C11—C121.504 (5)
C2—H2A0.9600C11—C141.520 (5)
C2—H2B0.9600C12—H12A0.9600
C2—H2C0.9600C12—H12B0.9600
C3—H3A0.9600C12—H12C0.9600
C3—H3B0.9600C13—H13A0.9600
C3—H3C0.9600C13—H13B0.9600
C4—H4A0.9600C13—H13C0.9600
C4—H4B0.9600C14—H14A0.9600
C4—H4C0.9600C14—H14B0.9600
C5—O01.220 (3)C14—H14C0.9600
C5—N11.335 (3)C15—O15"1.213 (4)
C5—O1.339 (3)C15—N111.329 (4)
N1—C1A1.460 (3)C15—O11"1.349 (3)
N1—H1A0.8600N11—C11A1.446 (4)
C1A—C1'1.528 (3)N11—H11A0.8600
C1A—C1B1.529 (4)C11A—C11'1.527 (4)
C1A—H1AA0.9800C11A—C11B1.531 (4)
C1B—C1G1.501 (4)C11A—H11B0.9800
C1B—H1BA0.9700C11B—C11G1.497 (4)
C1B—H1BB0.9700C11B—H11C0.9700
C1G—C1D21.389 (4)C11B—H11D0.9700
C1G—C1D11.399 (4)C11G—C11D1.382 (4)
C1D1—C1E11.371 (4)C11G—C11X1.399 (5)
C1D1—H1DA0.9300C11D—C11E1.390 (5)
C1E1—C1Z1.385 (4)C11D—H11E0.9300
C1E1—H1EA0.9300C11E—C11Z1.379 (5)
C1Z—O1Z1.358 (3)C11E—H11F0.9300
C1Z—C1E21.388 (4)C11Z—O11Z1.352 (4)
O1Z—H1ZA0.8200C11Z—C11Y1.387 (6)
C1E2—C1D21.376 (4)O11Z—H11G0.8200
C1E2—H1EB0.9300C11Y—C11X1.382 (5)
C1D2—H1DB0.9300C11Y—H11H0.9300
C1'—O11.236 (3)C11X—H11I0.9300
C1'—N21.325 (3)C11'—O111.227 (3)
N2—C2A1.461 (3)C11'—N121.330 (3)
N2—H2D0.8600N12—C12A1.469 (4)
C2A—C2'1.515 (3)N12—H12D0.8600
C2A—C2B1.517 (4)C12A—C12B1.505 (7)
C2A—H2AA0.9800C12A—C12'1.529 (5)
C2B—H2BA0.9600C12A—H12E0.9800
C2B—H2BB0.9600C12B—H12F0.9600
C2B—H2BC0.9600C12B—H12G0.9600
C2'—O21.235 (3)C12B—H12H0.9600
C2'—N31.318 (3)C12'—O121.238 (4)
N3—C3A1.451 (3)C12'—N131.305 (4)
N3—H3D0.8600N13—C13A1.437 (4)
C3A—C3'1.504 (4)N13—H13D0.8600
C3A—H3AA0.9700C13A—C13'1.509 (4)
C3A—H3AB0.9700C13A—H13E0.9700
C3'—O31.233 (3)C13A—H13F0.9700
C3'—N41.346 (3)C13'—O131.233 (3)
N4—C4A1.463 (3)C13'—N141.346 (3)
N4—C4N1.472 (3)N14—C14A1.461 (3)
C4N—H4NA0.9600N14—C14N1.462 (4)
C4N—H4NB0.9600C14N—H14D0.9600
C4N—H4NC0.9600C14N—H14E0.9600
C4A—C4B1.526 (4)C14N—H14F0.9600
C4A—C4'1.527 (3)C14A—C14'1.533 (3)
C4A—H4AA0.9800C14A—C14B1.536 (4)
C4B—C4G1.505 (4)C14A—H14G0.9800
C4B—H4BA0.9700C14B—C14G1.510 (4)
C4B—H4BB0.9700C14B—H14H0.9700
C4G—C4D11.386 (4)C14B—H14I0.9700
C4G—C4D21.392 (5)C14G—C14D1.381 (4)
C4D1—C4E11.373 (4)C14G—C14X1.385 (4)
C4D1—H4DA0.9300C14D—C14E1.386 (5)
C4E1—C4Z1.368 (6)C14D—H14J0.9300
C4E1—H4EA0.9300C14E—C14Z1.368 (5)
C4Z—C4E21.377 (5)C14E—H14K0.9300
C4Z—H4ZA0.9300C14Z—C14Y1.365 (5)
C4E2—C4D21.397 (5)C14Z—H14L0.9300
C4E2—H4EB0.9300C14Y—C14X1.383 (4)
C4D2—H4DB0.9300C14Y—H14M0.9300
C4'—O41.226 (3)C14X—H14N0.9300
C4'—N51.319 (4)C14'—O141.223 (3)
N5—C5A1.442 (3)C14'—N151.335 (3)
N5—H5A0.8600N15—C15A1.444 (3)
C5A—C5'1.516 (4)N15—H15A0.8600
C5A—C5B1.522 (4)C15A—C15'1.507 (4)
C5A—H5AA0.9800C15A—C15B1.546 (4)
C5B—C5G'1.503 (13)C15A—H15B0.9800
C5B—C5G1.574 (8)C15B—C15G1.516 (4)
C5B—H5BA0.9700C15B—H15C0.9700
C5B—H5BB0.9700C15B—H15D0.9700
C5G—S51.837 (7)C15G—S151.799 (3)
C5G—H5GA0.9700C15G—H15E0.9700
C5G—H5GB0.9700C15G—H15F0.9700
S5—C5D1.920 (9)S15—C15D1.742 (5)
C5D—H5DA0.9600C15D—H15G0.9600
C5D—H5DB0.9600C15D—H15H0.9600
C5D—H5DC0.9600C15D—H15I0.9600
C5G'—S5'1.678 (12)C15'—O151.196 (3)
C5G'—H5GC0.9700C15'—O15'1.342 (3)
C5G'—H5GD0.9700O15'—C161.434 (3)
S5'—C5D'1.896 (15)C16—H16A0.9600
C5D'—H5DD0.9600C16—H16B0.9600
C5D'—H5DE0.9600C16—H16C0.9600
C5D'—H5DF0.9600O1S—H1SA0.85 (4)
C5'—O51.203 (3)O1S—H1SB0.86 (3)
C5'—O5'1.311 (3)O2S—H2SA0.893 (17)
O5'—C61.444 (4)O2S—H2SB0.874 (18)
C6—H6A0.9600O3S—O3Si0.60 (3)
C6—H6B0.9600
O—C1—C2111.2 (2)C5'—O5'—C6117.0 (2)
O—C1—C3102.1 (3)O5'—C6—H6A109.5
C2—C1—C3111.1 (3)O5'—C6—H6B109.5
O—C1—C4108.5 (3)H6A—C6—H6B109.5
C2—C1—C4112.6 (3)O5'—C6—H6C109.5
C3—C1—C4110.8 (3)H6A—C6—H6C109.5
C1—C2—H2A109.5H6B—C6—H6C109.5
C1—C2—H2B109.5O11"—C11—C13110.4 (2)
H2A—C2—H2B109.5O11"—C11—C12109.1 (3)
C1—C2—H2C109.5C13—C11—C12113.0 (3)
H2A—C2—H2C109.5O11"—C11—C14101.9 (3)
H2B—C2—H2C109.5C13—C11—C14110.7 (3)
C1—C3—H3A109.5C12—C11—C14111.3 (3)
C1—C3—H3B109.5C11—C12—H12A109.5
H3A—C3—H3B109.5C11—C12—H12B109.5
C1—C3—H3C109.5H12A—C12—H12B109.5
H3A—C3—H3C109.5C11—C12—H12C109.5
H3B—C3—H3C109.5H12A—C12—H12C109.5
C1—C4—H4A109.5H12B—C12—H12C109.5
C1—C4—H4B109.5C11—C13—H13A109.5
H4A—C4—H4B109.5C11—C13—H13B109.5
C1—C4—H4C109.5H13A—C13—H13B109.5
H4A—C4—H4C109.5C11—C13—H13C109.5
H4B—C4—H4C109.5H13A—C13—H13C109.5
O0—C5—N1124.6 (2)H13B—C13—H13C109.5
O0—C5—O125.2 (2)C11—C14—H14A109.5
N1—C5—O110.2 (2)C11—C14—H14B109.5
C5—O—C1121.9 (2)H14A—C14—H14B109.5
C5—N1—C1A124.1 (2)C11—C14—H14C109.5
C5—N1—H1A118.0H14A—C14—H14C109.5
C1A—N1—H1A118.0H14B—C14—H14C109.5
N1—C1A—C1'106.8 (2)O15"—C15—N11125.6 (3)
N1—C1A—C1B109.07 (18)O15"—C15—O11"125.5 (3)
C1'—C1A—C1B112.0 (2)N11—C15—O11"108.9 (2)
N1—C1A—H1AA109.6C15—O11"—C11123.1 (2)
C1'—C1A—H1AA109.6C15—N11—C11A126.0 (3)
C1B—C1A—H1AA109.6C15—N11—H11A117.0
C1G—C1B—C1A116.52 (19)C11A—N11—H11A117.0
C1G—C1B—H1BA108.2N11—C11A—C11'106.7 (2)
C1A—C1B—H1BA108.2N11—C11A—C11B109.2 (2)
C1G—C1B—H1BB108.2C11'—C11A—C11B110.8 (2)
C1A—C1B—H1BB108.2N11—C11A—H11B110.0
H1BA—C1B—H1BB107.3C11'—C11A—H11B110.0
C1D2—C1G—C1D1117.0 (3)C11B—C11A—H11B110.0
C1D2—C1G—C1B121.4 (3)C11G—C11B—C11A115.7 (2)
C1D1—C1G—C1B121.5 (3)C11G—C11B—H11C108.4
C1E1—C1D1—C1G121.7 (3)C11A—C11B—H11C108.4
C1E1—C1D1—H1DA119.1C11G—C11B—H11D108.4
C1G—C1D1—H1DA119.1C11A—C11B—H11D108.4
C1D1—C1E1—C1Z120.3 (3)H11C—C11B—H11D107.4
C1D1—C1E1—H1EA119.8C11D—C11G—C11X117.0 (3)
C1Z—C1E1—H1EA119.8C11D—C11G—C11B120.7 (3)
O1Z—C1Z—C1E1118.8 (3)C11X—C11G—C11B122.3 (3)
O1Z—C1Z—C1E2122.4 (3)C11G—C11D—C11E122.6 (3)
C1E1—C1Z—C1E2118.8 (3)C11G—C11D—H11E118.7
C1Z—O1Z—H1ZA109.5C11E—C11D—H11E118.7
C1D2—C1E2—C1Z120.3 (3)C11Z—C11E—C11D119.4 (3)
C1D2—C1E2—H1EB119.8C11Z—C11E—H11F120.3
C1Z—C1E2—H1EB119.8C11D—C11E—H11F120.3
C1E2—C1D2—C1G121.7 (3)O11Z—C11Z—C11E122.0 (4)
C1E2—C1D2—H1DB119.2O11Z—C11Z—C11Y118.8 (4)
C1G—C1D2—H1DB119.2C11E—C11Z—C11Y119.1 (3)
O1—C1'—N2122.5 (2)C11Z—O11Z—H11G109.5
O1—C1'—C1A119.62 (19)C11X—C11Y—C11Z120.9 (3)
N2—C1'—C1A117.9 (2)C11X—C11Y—H11H119.5
C1'—N2—C2A120.2 (2)C11Z—C11Y—H11H119.6
C1'—N2—H2D119.9C11Y—C11X—C11G120.9 (3)
C2A—N2—H2D119.9C11Y—C11X—H11I119.6
N2—C2A—C2'108.4 (2)C11G—C11X—H11I119.6
N2—C2A—C2B111.6 (2)O11—C11'—N12123.2 (2)
C2'—C2A—C2B110.2 (2)O11—C11'—C11A119.3 (2)
N2—C2A—H2AA108.8N12—C11'—C11A117.5 (2)
C2'—C2A—H2AA108.8C11'—N12—C12A119.7 (2)
C2B—C2A—H2AA108.8C11'—N12—H12D120.1
C2A—C2B—H2BA109.5C12A—N12—H12D120.1
C2A—C2B—H2BB109.5N12—C12A—C12B113.0 (3)
H2BA—C2B—H2BB109.5N12—C12A—C12'108.0 (3)
C2A—C2B—H2BC109.5C12B—C12A—C12'110.7 (3)
H2BA—C2B—H2BC109.5N12—C12A—H12E108.3
H2BB—C2B—H2BC109.5C12B—C12A—H12E108.3
O2—C2'—N3122.6 (2)C12'—C12A—H12E108.3
O2—C2'—C2A120.8 (2)C12A—C12B—H12F109.5
N3—C2'—C2A116.6 (2)C12A—C12B—H12G109.5
C2'—N3—C3A120.6 (2)H12F—C12B—H12G109.5
C2'—N3—H3D119.7C12A—C12B—H12H109.5
C3A—N3—H3D119.7H12F—C12B—H12H109.5
N3—C3A—C3'111.8 (2)H12G—C12B—H12H109.5
N3—C3A—H3AA109.3O12—C12'—N13122.6 (3)
C3'—C3A—H3AA109.3O12—C12'—C12A122.4 (3)
N3—C3A—H3AB109.3N13—C12'—C12A115.0 (3)
C3'—C3A—H3AB109.3C12'—N13—C13A122.3 (3)
H3AA—C3A—H3AB107.9C12'—N13—H13D118.9
O3—C3'—N4123.8 (2)C13A—N13—H13D118.9
O3—C3'—C3A120.5 (2)N13—C13A—C13'110.5 (3)
N4—C3'—C3A115.7 (2)N13—C13A—H13E109.6
C3'—N4—C4A119.6 (2)C13'—C13A—H13E109.6
C3'—N4—C4N121.8 (2)N13—C13A—H13F109.6
C4A—N4—C4N118.52 (19)C13'—C13A—H13F109.6
N4—C4N—H4NA109.5H13E—C13A—H13F108.1
N4—C4N—H4NB109.5O13—C13'—N14123.8 (2)
H4NA—C4N—H4NB109.5O13—C13'—C13A120.2 (2)
N4—C4N—H4NC109.5N14—C13'—C13A116.0 (2)
H4NA—C4N—H4NC109.5C13'—N14—C14A118.2 (2)
H4NB—C4N—H4NC109.5C13'—N14—C14N122.6 (2)
N4—C4A—C4B112.4 (2)C14A—N14—C14N118.81 (19)
N4—C4A—C4'109.9 (2)N14—C14N—H14D109.5
C4B—C4A—C4'111.0 (2)N14—C14N—H14E109.5
N4—C4A—H4AA107.8H14D—C14N—H14E109.5
C4B—C4A—H4AA107.8N14—C14N—H14F109.5
C4'—C4A—H4AA107.8H14D—C14N—H14F109.5
C4G—C4B—C4A112.0 (2)H14E—C14N—H14F109.5
C4G—C4B—H4BA109.2N14—C14A—C14'112.0 (2)
C4A—C4B—H4BA109.2N14—C14A—C14B112.1 (2)
C4G—C4B—H4BB109.2C14'—C14A—C14B110.87 (18)
C4A—C4B—H4BB109.2N14—C14A—H14G107.2
H4BA—C4B—H4BB107.9C14'—C14A—H14G107.2
C4D1—C4G—C4D2118.6 (3)C14B—C14A—H14G107.2
C4D1—C4G—C4B121.2 (3)C14G—C14B—C14A111.26 (19)
C4D2—C4G—C4B120.1 (3)C14G—C14B—H14H109.4
C4E1—C4D1—C4G121.4 (3)C14A—C14B—H14H109.4
C4E1—C4D1—H4DA119.3C14G—C14B—H14I109.4
C4G—C4D1—H4DA119.3C14A—C14B—H14I109.4
C4Z—C4E1—C4D1120.3 (3)H14H—C14B—H14I108.0
C4Z—C4E1—H4EA119.9C14D—C14G—C14X117.5 (3)
C4D1—C4E1—H4EA119.9C14D—C14G—C14B121.6 (3)
C4E1—C4Z—C4E2119.5 (3)C14X—C14G—C14B120.9 (3)
C4E1—C4Z—H4ZA120.2C14G—C14D—C14E121.5 (3)
C4E2—C4Z—H4ZA120.2C14G—C14D—H14J119.3
C4Z—C4E2—C4D2120.9 (3)C14E—C14D—H14J119.3
C4Z—C4E2—H4EB119.6C14Z—C14E—C14D120.1 (3)
C4D2—C4E2—H4EB119.6C14Z—C14E—H14K119.9
C4G—C4D2—C4E2119.3 (3)C14D—C14E—H14K119.9
C4G—C4D2—H4DB120.3C14Y—C14Z—C14E119.2 (3)
C4E2—C4D2—H4DB120.3C14Y—C14Z—H14L120.4
O4—C4'—N5122.2 (2)C14E—C14Z—H14L120.4
O4—C4'—C4A122.5 (3)C14Z—C14Y—C14X121.0 (3)
N5—C4'—C4A115.3 (2)C14Z—C14Y—H14M119.5
C4'—N5—C5A122.6 (2)C14X—C14Y—H14M119.5
C4'—N5—H5A118.7C14Y—C14X—C14G120.7 (3)
C5A—N5—H5A118.7C14Y—C14X—H14N119.6
N5—C5A—C5'110.3 (2)C14G—C14X—H14N119.6
N5—C5A—C5B110.0 (2)O14—C14'—N15123.4 (2)
C5'—C5A—C5B111.3 (2)O14—C14'—C14A122.9 (2)
N5—C5A—H5AA108.4N15—C14'—C14A113.6 (2)
C5'—C5A—H5AA108.4C14'—N15—C15A123.9 (2)
C5B—C5A—H5AA108.4C14'—N15—H15A118.0
C5G'—C5B—C5A121.3 (6)C15A—N15—H15A118.0
C5G'—C5B—C5G15.3 (7)N15—C15A—C15'108.0 (2)
C5A—C5B—C5G106.2 (3)N15—C15A—C15B110.92 (19)
C5G'—C5B—H5BA103.7C15'—C15A—C15B113.7 (2)
C5A—C5B—H5BA110.5N15—C15A—H15B108.0
C5G—C5B—H5BA110.5C15'—C15A—H15B108.0
C5G'—C5B—H5BB101.2C15B—C15A—H15B108.0
C5A—C5B—H5BB110.5C15G—C15B—C15A114.6 (2)
C5G—C5B—H5BB110.5C15G—C15B—H15C108.6
H5BA—C5B—H5BB108.7C15A—C15B—H15C108.6
C5B—C5G—S5112.0 (5)C15G—C15B—H15D108.6
C5B—C5G—H5GA109.2C15A—C15B—H15D108.6
S5—C5G—H5GA109.2H15C—C15B—H15D107.6
C5B—C5G—H5GB109.2C15B—C15G—S15114.28 (19)
S5—C5G—H5GB109.2C15B—C15G—H15E108.7
H5GA—C5G—H5GB107.9S15—C15G—H15E108.7
C5G—S5—C5D98.1 (4)C15B—C15G—H15F108.7
S5—C5D—H5DA109.5S15—C15G—H15F108.7
S5—C5D—H5DB109.5H15E—C15G—H15F107.6
H5DA—C5D—H5DB109.5C15D—S15—C15G103.3 (2)
S5—C5D—H5DC109.5S15—C15D—H15G109.5
H5DA—C5D—H5DC109.5S15—C15D—H15H109.5
H5DB—C5D—H5DC109.5H15G—C15D—H15H109.5
C5B—C5G'—S5'121.5 (8)S15—C15D—H15I109.5
C5B—C5G'—H5GC106.9H15G—C15D—H15I109.5
S5'—C5G'—H5GC107.0H15H—C15D—H15I109.5
C5B—C5G'—H5GD107.0O15—C15'—O15'123.4 (2)
S5'—C5G'—H5GD107.0O15—C15'—C15A125.4 (2)
H5GC—C5G'—H5GD106.7O15'—C15'—C15A111.1 (2)
C5G'—S5'—C5D'92.7 (7)C15'—O15'—C16116.0 (2)
S5'—C5D'—H5DD109.5O15'—C16—H16A109.5
S5'—C5D'—H5DE109.5O15'—C16—H16B109.5
H5DD—C5D'—H5DE109.5H16A—C16—H16B109.5
S5'—C5D'—H5DF109.5O15'—C16—H16C109.5
H5DD—C5D'—H5DF109.5H16A—C16—H16C109.5
H5DE—C5D'—H5DF109.5H16B—C16—H16C109.5
O5—C5'—O5'123.9 (2)H1SA—O1S—H1SB110 (3)
O5—C5'—C5A124.0 (2)H2SA—O2S—H2SB108 (3)
O5'—C5'—C5A112.1 (2)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O150.862.293.036 (3)145
O1Z—H1ZA···O1S0.821.892.708 (3)179
N2—H2D···O2ii0.862.112.960 (3)169
N3—H3D···O130.862.263.029 (3)149
N5—H5A···O110.862.072.865 (3)153
N11—H11A···O50.862.263.017 (3)146
O11Z—H11G···O2Siii0.821.932.745 (5)175
N12—H12D···O12i0.862.102.956 (4)171
N13—H13D···O30.862.052.902 (3)169
N15—H15A···O10.862.002.828 (3)161
O1S—H1SA···O2iv0.85 (4)2.02 (4)2.842 (3)164 (3)
O1S—H1SB···O0iii0.86 (3)2.00 (3)2.827 (3)160 (4)
O2S—H2SA···O15"0.89 (2)1.93 (2)2.821 (3)175 (4)
O2S—H2SB···O3Si0.87 (2)1.76 (3)2.521 (14)144 (4)
O2S—H2SB···O3S0.87 (2)2.01 (3)2.768 (14)144 (3)
Symmetry codes: (i) x, y, z; (ii) x, y, z+1; (iii) x, y+1, z; (iv) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC35H49N5O9S·H2O·0.125O
Mr735.87
Crystal system, space groupMonoclinic, C2
Temperature (K)153
a, b, c (Å)38.354 (1), 11.000 (1), 22.689 (1)
β (°) 123.15 (1)
V3)8014.4 (8)
Z8
Radiation typeCu Kα
µ (mm1)1.21
Crystal size (mm)0.52 × 0.50 × 0.46
Data collection
DiffractometerBruker SMART 6000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.559, 0.573
No. of measured, independent and
observed [I > 2σ(I)] reflections
17149, 10567, 8802
Rint0.033
(sin θ/λ)max1)0.588
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.112, 1.01
No. of reflections10567
No. of parameters966
No. of restraints11
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.23
Absolute structureFlack (1983)
Absolute structure parameter0.00 (2)

Computer programs: SMART (Bruker, 1999), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXS97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O150.862.293.036 (3)145.1
O1Z—H1ZA···O1S0.821.892.708 (3)179.3
N2—H2D···O2i0.862.112.960 (3)169.0
N3—H3D···O130.862.263.029 (3)148.8
N5—H5A···O110.862.072.865 (3)152.5
N11—H11A···O50.862.263.017 (3)146.4
O11Z—H11G···O2Sii0.821.932.745 (5)175.2
N12—H12D···O12iii0.862.102.956 (4)170.5
N13—H13D···O30.862.052.902 (3)168.9
N15—H15A···O10.862.002.828 (3)160.5
O1S—H1SA···O2iv0.85 (4)2.02 (4)2.842 (3)164 (3)
O1S—H1SB···O0ii0.86 (3)2.00 (3)2.827 (3)160 (4)
O2S—H2SA···O15"0.89 (2)1.93 (2)2.821 (3)175 (4)
O2S—H2SB···O3Siii0.87 (2)1.76 (3)2.521 (14)144 (4)
O2S—H2SB···O3S0.87 (2)2.01 (3)2.768 (14)144 (3)
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z; (iii) x, y, z; (iv) x, y+1, z+1.
 

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