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The title compound, C13H17NO7S2, was designed as a precursor of human leukocyte elastase inhibitors. The title compound belongs to a series of monocyclic C-methylthiol­ated β-lactam sulfones with different substituents at the ring N atom and the C atom opposite. The compound crystallizes with two independent molecules in the asymmetric unit differing mainly in the orientation of the phenyl ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022705/ac6025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022705/ac6025Isup2.hkl
Contains datablock I

CCDC reference: 202992

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.115
  • Data-to-parameter ratio = 11.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 67.21 From the CIF: _reflns_number_total 4996 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5981 Completeness (_total/calc) 83.53% Alert A: < 85% complete (theta max?)
Author response: It is extremely difficult to get complete, or nearly complete, coverage of triclinic crystals when using our CCD detector with CuKa radiation. The advantage of using the CCD with CuKa is that the fraction of observed reflectiuons reletive to the total number of reflections is usually high (i.e. 4587 observed / 4996 total ~ 92%).

Yellow Alert Alert Level C:
PLAT_601 Alert C Structure Contains Solvent Accessible VOIDS of 34.00 A   3
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

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

3-Methoxy-1-(4-methoxyphenyl)-4,4-bis(methylsulfoxy)azetidin-2-one top
Crystal data top
C13H17NO7S2Z = 4
Mr = 363.40F(000) = 760
Triclinic, P1Dx = 1.444 Mg m3
a = 8.0552 (1) ÅCu Kα radiation, λ = 1.54178 Å
b = 11.6680 (1) ÅCell parameters from 7139 reflections
c = 18.3257 (2) Åθ = 2.5–67.1°
α = 95.079 (1)°µ = 3.21 mm1
β = 102.171 (1)°T = 193 K
γ = 93.226 (1)°Prism, colorless
V = 1672.10 (3) Å30.26 × 0.11 × 0.10 mm
Data collection top
Bruker SMART 6000 CCD
diffractometer
4996 independent reflections
Radiation source: rotating anode4587 reflections with I > 2σ(I)
Gobel optics monochromatorRint = 0.033
ω scansθmax = 67.2°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 98
Tmin = 0.452, Tmax = 0.729k = 1312
8699 measured reflectionsl = 2121
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)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.2601P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
4996 reflectionsΔρmax = 0.25 e Å3
422 parametersΔρmin = 0.34 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0136 (7)
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
N10.9487 (2)0.99549 (14)0.32328 (9)0.0420 (4)
C1'0.8802 (2)1.05737 (17)0.37963 (11)0.0432 (4)
C2'0.8689 (3)1.1751 (2)0.37845 (13)0.0574 (5)
H2'A0.90951.21330.34260.069*
C3'0.7977 (4)1.2355 (2)0.43028 (15)0.0638 (6)
H3'A0.79161.31480.42980.077*
C4'0.7345 (3)1.1787 (2)0.48344 (12)0.0516 (5)
O4'0.6590 (2)1.24615 (16)0.52927 (10)0.0680 (5)
C4'A0.5934 (4)1.1937 (3)0.58554 (17)0.0773 (8)
H4'A0.54371.25060.61360.116*
H4'B0.68411.16210.61870.116*
H4'C0.50821.13310.56230.116*
C5'0.7498 (3)1.0620 (2)0.48579 (12)0.0545 (5)
H5'A0.71021.02380.52200.065*
C6'0.8243 (3)1.00150 (19)0.43413 (12)0.0508 (5)
H6'A0.83660.92300.43630.061*
C21.1046 (2)1.00608 (17)0.30416 (12)0.0450 (4)
O21.2372 (2)1.05647 (15)0.33641 (10)0.0633 (4)
C31.0379 (3)0.93327 (18)0.22897 (12)0.0443 (4)
H31.012 (3)0.981 (2)0.1876 (14)0.053*
O31.12763 (19)0.84222 (14)0.21118 (9)0.0568 (4)
C3A1.1268 (5)0.8213 (3)0.13296 (17)0.0885 (10)
H3AA1.19160.75660.12490.133*
H3AB1.17660.88840.11650.133*
H3AC1.01160.80490.10500.133*
C40.8703 (2)0.91198 (16)0.26045 (10)0.0399 (4)
S10.68230 (6)0.95737 (5)0.19885 (3)0.05078 (17)
O1A0.7331 (2)1.06814 (16)0.17915 (11)0.0707 (5)
O1B0.6292 (2)0.86569 (18)0.14054 (10)0.0775 (5)
C1C0.5244 (3)0.9766 (3)0.25076 (17)0.0724 (7)
H1CA0.42431.00050.21910.109*
H1CB0.56551.03450.29220.109*
H1CC0.49700.90510.26940.109*
S20.83851 (6)0.76776 (4)0.29175 (3)0.04722 (17)
O2A0.6774 (2)0.76282 (15)0.31278 (11)0.0667 (5)
O2B0.9887 (2)0.75806 (14)0.34767 (10)0.0640 (4)
C2C0.8284 (3)0.6638 (2)0.21549 (16)0.0658 (6)
H2CA0.81200.58820.23090.099*
H2CB0.93280.67010.19820.099*
H2CC0.73490.67630.17560.099*
N110.4266 (2)0.37977 (15)0.21815 (9)0.0439 (4)
C11'0.3658 (2)0.40650 (17)0.28522 (11)0.0436 (4)
C12'0.3898 (3)0.3309 (2)0.33909 (13)0.0584 (6)
H12A0.44580.26470.33150.070*
C13'0.3317 (4)0.3519 (2)0.40448 (14)0.0644 (6)
H13A0.35020.30090.44110.077*
C14'0.2463 (3)0.4488 (2)0.41511 (13)0.0560 (5)
O14'0.1820 (3)0.47746 (18)0.47628 (10)0.0798 (6)
C14A0.2169 (5)0.4099 (3)0.53760 (16)0.0908 (10)
H14A0.16200.43930.57620.136*
H14B0.33770.41340.55710.136*
H14C0.17480.33130.52100.136*
C15'0.2202 (3)0.5241 (2)0.36033 (14)0.0620 (6)
H15A0.16050.58880.36700.074*
C16'0.2815 (3)0.5046 (2)0.29606 (13)0.0560 (5)
H16A0.26630.55690.26020.067*
C120.5869 (3)0.35633 (18)0.20864 (12)0.0460 (5)
O120.7248 (2)0.37519 (16)0.24941 (9)0.0651 (4)
C130.5158 (2)0.29696 (19)0.12951 (11)0.0442 (4)
H130.509 (3)0.215 (2)0.1320 (13)0.053*
O130.5895 (2)0.32710 (14)0.07193 (8)0.0549 (4)
C13A0.5943 (5)0.2339 (3)0.01705 (16)0.0825 (8)
H13B0.64750.26120.02100.124*
H13C0.48020.20270.00540.124*
H13D0.65820.17500.04050.124*
C140.3417 (2)0.34628 (17)0.14070 (11)0.0415 (4)
S110.16578 (6)0.23419 (5)0.12530 (3)0.04935 (17)
O11A0.0944 (2)0.22094 (17)0.04683 (10)0.0735 (5)
O11B0.2375 (2)0.13749 (15)0.15927 (11)0.0698 (5)
C11C0.0143 (3)0.2841 (2)0.17402 (18)0.0708 (7)
H11A0.07950.22680.16690.106*
H11B0.02620.35410.15530.106*
H11C0.06550.29890.22650.106*
S120.28541 (6)0.47460 (4)0.09142 (3)0.04868 (17)
O12A0.1274 (2)0.50808 (15)0.10762 (10)0.0643 (4)
O12B0.4326 (2)0.55445 (15)0.11502 (10)0.0644 (4)
C12C0.2555 (3)0.4339 (2)0.00546 (13)0.0616 (6)
H12B0.22600.49930.03250.092*
H12C0.16530.37370.02050.092*
H12D0.35880.40650.01620.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0363 (8)0.0448 (9)0.0467 (9)0.0018 (6)0.0128 (7)0.0056 (7)
C1'0.0379 (10)0.0489 (11)0.0436 (10)0.0041 (7)0.0104 (8)0.0048 (8)
C2'0.0719 (15)0.0487 (13)0.0592 (13)0.0057 (9)0.0284 (11)0.0124 (10)
C3'0.0824 (17)0.0496 (13)0.0672 (14)0.0136 (11)0.0305 (13)0.0092 (11)
C4'0.0433 (11)0.0647 (14)0.0474 (11)0.0101 (9)0.0112 (9)0.0011 (10)
O4'0.0724 (11)0.0779 (12)0.0605 (10)0.0228 (8)0.0274 (8)0.0026 (8)
C4'A0.0678 (17)0.095 (2)0.0774 (17)0.0034 (13)0.0396 (14)0.0035 (15)
C5'0.0558 (13)0.0634 (14)0.0486 (11)0.0009 (9)0.0209 (10)0.0086 (10)
C6'0.0549 (12)0.0504 (12)0.0503 (11)0.0049 (8)0.0165 (9)0.0096 (9)
C20.0392 (11)0.0444 (11)0.0544 (11)0.0004 (8)0.0157 (9)0.0104 (9)
O20.0462 (9)0.0682 (10)0.0729 (10)0.0119 (7)0.0169 (8)0.0051 (8)
C30.0401 (10)0.0480 (11)0.0486 (11)0.0015 (7)0.0168 (9)0.0094 (9)
O30.0515 (9)0.0591 (9)0.0650 (9)0.0068 (6)0.0262 (7)0.0010 (7)
C3A0.116 (3)0.081 (2)0.0787 (18)0.0078 (16)0.0567 (18)0.0144 (16)
C40.0362 (10)0.0431 (10)0.0426 (9)0.0030 (7)0.0112 (8)0.0096 (8)
S10.0404 (3)0.0593 (3)0.0526 (3)0.0032 (2)0.0051 (2)0.0183 (2)
O1A0.0573 (10)0.0699 (11)0.0903 (13)0.0094 (7)0.0130 (9)0.0426 (10)
O1B0.0735 (12)0.0870 (13)0.0602 (10)0.0012 (9)0.0082 (9)0.0026 (9)
C1C0.0398 (12)0.097 (2)0.0862 (18)0.0175 (11)0.0143 (12)0.0300 (15)
S20.0489 (3)0.0430 (3)0.0536 (3)0.00230 (19)0.0169 (2)0.0126 (2)
O2A0.0645 (11)0.0621 (10)0.0856 (12)0.0004 (7)0.0393 (9)0.0214 (9)
O2B0.0664 (10)0.0581 (10)0.0667 (10)0.0130 (7)0.0040 (8)0.0226 (8)
C2C0.0720 (16)0.0483 (13)0.0774 (16)0.0060 (10)0.0228 (13)0.0009 (12)
N110.0370 (9)0.0534 (10)0.0432 (8)0.0072 (6)0.0090 (7)0.0125 (7)
C11'0.0414 (10)0.0473 (11)0.0446 (10)0.0062 (7)0.0115 (8)0.0110 (8)
C12'0.0690 (15)0.0580 (14)0.0572 (13)0.0270 (10)0.0224 (11)0.0199 (11)
C13'0.0803 (17)0.0681 (16)0.0561 (13)0.0268 (12)0.0254 (12)0.0293 (12)
C14'0.0638 (14)0.0607 (14)0.0512 (12)0.0147 (10)0.0227 (10)0.0160 (10)
O14'0.1083 (16)0.0852 (13)0.0670 (11)0.0388 (11)0.0498 (11)0.0284 (10)
C14A0.126 (3)0.103 (2)0.0623 (16)0.034 (2)0.0462 (18)0.0326 (16)
C15'0.0788 (16)0.0561 (14)0.0610 (13)0.0271 (11)0.0274 (12)0.0169 (11)
C16'0.0700 (15)0.0523 (13)0.0528 (12)0.0204 (10)0.0195 (11)0.0200 (10)
C120.0382 (11)0.0531 (12)0.0492 (11)0.0063 (8)0.0099 (9)0.0160 (9)
O120.0395 (8)0.0927 (13)0.0604 (9)0.0076 (7)0.0028 (7)0.0098 (9)
C130.0398 (10)0.0478 (11)0.0488 (11)0.0064 (7)0.0137 (8)0.0134 (9)
O130.0541 (9)0.0642 (10)0.0533 (8)0.0045 (6)0.0241 (7)0.0130 (7)
C13A0.108 (2)0.089 (2)0.0574 (14)0.0149 (16)0.0341 (15)0.0035 (14)
C140.0375 (10)0.0453 (11)0.0438 (10)0.0025 (7)0.0103 (8)0.0122 (8)
S110.0417 (3)0.0513 (3)0.0565 (3)0.00347 (19)0.0116 (2)0.0153 (2)
O11A0.0682 (11)0.0852 (13)0.0586 (10)0.0230 (9)0.0013 (8)0.0087 (9)
O11B0.0616 (10)0.0560 (10)0.0975 (13)0.0021 (7)0.0205 (9)0.0332 (9)
C11C0.0473 (13)0.0762 (17)0.0951 (19)0.0040 (11)0.0293 (13)0.0153 (14)
S120.0445 (3)0.0504 (3)0.0528 (3)0.00508 (19)0.0076 (2)0.0212 (2)
O12A0.0565 (9)0.0701 (11)0.0737 (11)0.0244 (7)0.0169 (8)0.0279 (9)
O12B0.0637 (10)0.0542 (9)0.0727 (10)0.0078 (7)0.0060 (8)0.0216 (8)
C12C0.0597 (14)0.0758 (16)0.0500 (12)0.0021 (11)0.0057 (10)0.0272 (11)
Geometric parameters (Å, º) top
N1—C21.376 (3)N11—C121.378 (3)
N1—C1'1.430 (3)N11—C11'1.432 (3)
N1—C41.449 (2)N11—C141.448 (3)
C1'—C6'1.377 (3)C11'—C12'1.372 (3)
C1'—C2'1.383 (3)C11'—C16'1.384 (3)
C2'—C3'1.373 (3)C12'—C13'1.383 (3)
C2'—H2'A0.9300C12'—H12A0.9300
C3'—C4'1.390 (3)C13'—C14'1.376 (3)
C3'—H3'A0.9300C13'—H13A0.9300
C4'—O4'1.359 (3)C14'—O14'1.355 (3)
C4'—C5'1.378 (3)C14'—C15'1.383 (3)
O4'—C4'A1.422 (3)O14'—C14A1.418 (3)
C4'A—H4'A0.9600C14A—H14A0.9600
C4'A—H4'B0.9600C14A—H14B0.9600
C4'A—H4'C0.9600C14A—H14C0.9600
C5'—C6'1.387 (3)C15'—C16'1.376 (3)
C5'—H5'A0.9300C15'—H15A0.9300
C6'—H6'A0.9300C16'—H16A0.9300
C2—O21.199 (3)C12—O121.197 (3)
C2—C31.529 (3)C12—C131.529 (3)
C3—O31.372 (2)C13—O131.377 (2)
C3—C41.591 (3)C13—C141.591 (3)
C3—H30.98 (3)C13—H130.96 (2)
O3—C3A1.431 (3)O13—C13A1.422 (3)
C3A—H3AA0.9600C13A—H13B0.9600
C3A—H3AB0.9600C13A—H13C0.9600
C3A—H3AC0.9600C13A—H13D0.9600
C4—S11.8232 (19)C14—S111.8317 (19)
C4—S21.8468 (19)C14—S121.845 (2)
S1—O1B1.4222 (19)S11—O11A1.4228 (18)
S1—O1A1.4329 (18)S11—O11B1.4285 (18)
S1—C1C1.754 (3)S11—C11C1.753 (3)
C1C—H1CA0.9600C11C—H11A0.9600
C1C—H1CB0.9600C11C—H11B0.9600
C1C—H1CC0.9600C11C—H11C0.9600
S2—O2B1.4280 (18)S12—O12B1.4316 (17)
S2—O2A1.4287 (17)S12—O12A1.4340 (17)
S2—C2C1.752 (2)S12—C12C1.759 (2)
C2C—H2CA0.9600C12C—H12B0.9600
C2C—H2CB0.9600C12C—H12C0.9600
C2C—H2CC0.9600C12C—H12D0.9600
C2—N1—C1'131.98 (17)C12—N11—C11'130.44 (17)
C2—N1—C495.63 (15)C12—N11—C1495.47 (15)
C1'—N1—C4131.89 (15)C11'—N11—C14133.13 (16)
C6'—C1'—C2'119.90 (19)C12'—C11'—C16'119.76 (19)
C6'—C1'—N1121.08 (18)C12'—C11'—N11118.45 (18)
C2'—C1'—N1119.01 (18)C16'—C11'—N11121.77 (18)
C3'—C2'—C1'120.0 (2)C11'—C12'—C13'120.7 (2)
C3'—C2'—H2'A120.0C11'—C12'—H12A119.6
C1'—C2'—H2'A120.0C13'—C12'—H12A119.6
C2'—C3'—C4'120.3 (2)C14'—C13'—C12'119.6 (2)
C2'—C3'—H3'A119.8C14'—C13'—H13A120.2
C4'—C3'—H3'A119.8C12'—C13'—H13A120.2
O4'—C4'—C5'125.2 (2)O14'—C14'—C13'124.8 (2)
O4'—C4'—C3'115.1 (2)O14'—C14'—C15'115.7 (2)
C5'—C4'—C3'119.6 (2)C13'—C14'—C15'119.5 (2)
C4'—O4'—C4'A118.0 (2)C14'—O14'—C14A118.7 (2)
O4'—C4'A—H4'A109.5O14'—C14A—H14A109.5
O4'—C4'A—H4'B109.5O14'—C14A—H14B109.5
H4'A—C4'A—H4'B109.5H14A—C14A—H14B109.5
O4'—C4'A—H4'C109.5O14'—C14A—H14C109.5
H4'A—C4'A—H4'C109.5H14A—C14A—H14C109.5
H4'B—C4'A—H4'C109.5H14B—C14A—H14C109.5
C4'—C5'—C6'119.9 (2)C16'—C15'—C14'120.8 (2)
C4'—C5'—H5'A120.1C16'—C15'—H15A119.6
C6'—C5'—H5'A120.1C14'—C15'—H15A119.6
C1'—C6'—C5'120.2 (2)C15'—C16'—C11'119.4 (2)
C1'—C6'—H6'A119.9C15'—C16'—H16A120.3
C5'—C6'—H6'A119.9C11'—C16'—H16A120.3
O2—C2—N1131.5 (2)O12—C12—N11132.0 (2)
O2—C2—C3136.33 (19)O12—C12—C13136.0 (2)
N1—C2—C392.17 (15)N11—C12—C1391.95 (15)
O3—C3—C2117.97 (18)O13—C13—C12118.83 (17)
O3—C3—C4120.39 (17)O13—C13—C14121.00 (17)
C2—C3—C484.26 (14)C12—C13—C1484.20 (14)
O3—C3—H3111.4 (14)O13—C13—H13112.0 (14)
C2—C3—H3111.7 (14)C12—C13—H13108.4 (14)
C4—C3—H3108.3 (14)C14—C13—H13109.2 (14)
C3—O3—C3A114.3 (2)C13—O13—C13A114.17 (19)
O3—C3A—H3AA109.5O13—C13A—H13B109.5
O3—C3A—H3AB109.5O13—C13A—H13C109.5
H3AA—C3A—H3AB109.5H13B—C13A—H13C109.5
O3—C3A—H3AC109.5O13—C13A—H13D109.5
H3AA—C3A—H3AC109.5H13B—C13A—H13D109.5
H3AB—C3A—H3AC109.5H13C—C13A—H13D109.5
N1—C4—C387.02 (14)N11—C14—C1386.91 (14)
N1—C4—S1114.94 (13)N11—C14—S11115.94 (13)
C3—C4—S1112.10 (13)C13—C14—S11112.92 (13)
N1—C4—S2111.00 (13)N11—C14—S12110.72 (13)
C3—C4—S2115.31 (13)C13—C14—S12114.47 (13)
S1—C4—S2113.81 (10)S11—C14—S12113.34 (10)
O1B—S1—O1A118.38 (12)O11A—S11—O11B118.47 (13)
O1B—S1—C1C110.46 (14)O11A—S11—C11C109.66 (14)
O1A—S1—C1C107.77 (13)O11B—S11—C11C108.51 (13)
O1B—S1—C4105.88 (11)O11A—S11—C14106.35 (9)
O1A—S1—C4105.52 (10)O11B—S11—C14105.47 (10)
C1C—S1—C4108.35 (11)C11C—S11—C14107.83 (11)
S1—C1C—H1CA109.5S11—C11C—H11A109.5
S1—C1C—H1CB109.5S11—C11C—H11B109.5
H1CA—C1C—H1CB109.5H11A—C11C—H11B109.5
S1—C1C—H1CC109.5S11—C11C—H11C109.5
H1CA—C1C—H1CC109.5H11A—C11C—H11C109.5
H1CB—C1C—H1CC109.5H11B—C11C—H11C109.5
O2B—S2—O2A118.74 (11)O12B—S12—O12A118.33 (12)
O2B—S2—C2C109.64 (12)O12B—S12—C12C109.04 (12)
O2A—S2—C2C108.47 (12)O12A—S12—C12C109.03 (11)
O2B—S2—C4104.24 (10)O12B—S12—C14104.80 (9)
O2A—S2—C4106.85 (9)O12A—S12—C14107.34 (9)
C2C—S2—C4108.42 (11)C12C—S12—C14107.79 (11)
S2—C2C—H2CA109.5S12—C12C—H12B109.5
S2—C2C—H2CB109.5S12—C12C—H12C109.5
H2CA—C2C—H2CB109.5H12B—C12C—H12C109.5
S2—C2C—H2CC109.5S12—C12C—H12D109.5
H2CA—C2C—H2CC109.5H12B—C12C—H12D109.5
H2CB—C2C—H2CC109.5H12C—C12C—H12D109.5
N1—C2—C3—C47.08 (15)N1—C4—S2—C2C156.18 (14)
C2—N1—C1'—C2'59.6 (3)C3—C4—S2—C2C59.29 (17)
C2—C3—O3—C3A145.6 (2)S1—C4—S2—C2C72.28 (14)
N11—C12—C13—C148.93 (14)C12—N11—C11'—C12'55.4 (3)
C14—N11—C11'—C12'110.5 (3)C12—N11—C11'—C16'125.9 (2)
C12—C13—O13—C13A144.5 (2)C14—N11—C11'—C16'68.2 (3)
C2—N1—C1'—C6'121.0 (2)C16'—C11'—C12'—C13'0.5 (4)
C4—N1—C1'—C6'69.2 (3)N11—C11'—C12'—C13'179.2 (2)
C4—N1—C1'—C2'110.2 (2)C11'—C12'—C13'—C14'1.1 (4)
C6'—C1'—C2'—C3'1.8 (4)C12'—C13'—C14'—O14'179.1 (3)
N1—C1'—C2'—C3'177.5 (2)C12'—C13'—C14'—C15'0.2 (4)
C1'—C2'—C3'—C4'0.9 (4)C13'—C14'—O14'—C14A6.2 (5)
C2'—C3'—C4'—O4'176.7 (2)C15'—C14'—O14'—C14A174.5 (3)
C2'—C3'—C4'—C5'2.6 (4)O14'—C14'—C15'—C16'179.3 (3)
C5'—C4'—O4'—C4'A1.5 (4)C13'—C14'—C15'—C16'1.3 (4)
C3'—C4'—O4'—C4'A179.3 (2)C14'—C15'—C16'—C11'1.9 (4)
O4'—C4'—C5'—C6'177.7 (2)C12'—C11'—C16'—C15'1.1 (4)
C3'—C4'—C5'—C6'1.5 (4)N11—C11'—C16'—C15'177.7 (2)
C2'—C1'—C6'—C5'2.9 (3)C11'—N11—C12—O1218.7 (4)
N1—C1'—C6'—C5'176.46 (19)C14—N11—C12—O12171.5 (2)
C4'—C5'—C6'—C1'1.2 (3)C11'—N11—C12—C13159.9 (2)
C1'—N1—C2—O214.3 (4)C14—N11—C12—C139.81 (16)
C4—N1—C2—O2173.3 (2)O12—C12—C13—O1350.2 (4)
C1'—N1—C2—C3164.6 (2)N11—C12—C13—O13131.28 (19)
C4—N1—C2—C37.78 (16)O12—C12—C13—C14172.5 (3)
O2—C2—C3—O352.6 (4)C14—C13—O13—C13A114.1 (2)
N1—C2—C3—O3128.57 (18)C12—N11—C14—C139.43 (15)
O2—C2—C3—C4174.1 (3)C11'—N11—C14—C13159.8 (2)
C4—C3—O3—C3A114.0 (2)C12—N11—C14—S11123.48 (15)
C2—N1—C4—C37.48 (16)C11'—N11—C14—S1145.8 (3)
C1'—N1—C4—C3164.9 (2)C12—N11—C14—S12105.60 (14)
C2—N1—C4—S1120.51 (14)C11'—N11—C14—S1285.1 (2)
C1'—N1—C4—S151.9 (2)O13—C13—C14—N11128.79 (19)
C2—N1—C4—S2108.53 (14)C12—C13—C14—N118.50 (14)
C1'—N1—C4—S279.1 (2)O13—C13—C14—S11114.28 (19)
O3—C3—C4—N1125.91 (19)C12—C13—C14—S11125.42 (14)
C2—C3—C4—N16.73 (14)O13—C13—C14—S1217.4 (2)
O3—C3—C4—S1118.33 (18)C12—C13—C14—S12102.89 (15)
C2—C3—C4—S1122.49 (14)N11—C14—S11—O11A176.02 (15)
O3—C3—C4—S214.0 (2)C13—C14—S11—O11A85.89 (16)
C2—C3—C4—S2105.13 (15)S12—C14—S11—O11A46.36 (15)
N1—C4—S1—O1B178.33 (14)N11—C14—S11—O11B57.34 (17)
C3—C4—S1—O1B81.04 (16)C13—C14—S11—O11B40.75 (17)
S2—C4—S1—O1B52.09 (14)S12—C14—S11—O11B172.99 (11)
N1—C4—S1—O1A52.04 (16)N11—C14—S11—C11C58.46 (18)
C3—C4—S1—O1A45.25 (17)C13—C14—S11—C11C156.54 (16)
S2—C4—S1—O1A178.37 (11)S12—C14—S11—C11C71.21 (15)
N1—C4—S1—C1C63.17 (18)N11—C14—S12—O12B43.27 (16)
C3—C4—S1—C1C160.45 (16)C13—C14—S12—O12B52.98 (17)
S2—C4—S1—C1C66.42 (15)S11—C14—S12—O12B175.53 (11)
N1—C4—S2—O2B39.43 (15)N11—C14—S12—O12A83.37 (15)
C3—C4—S2—O2B57.46 (16)C13—C14—S12—O12A179.62 (14)
S1—C4—S2—O2B170.97 (11)S11—C14—S12—O12A48.89 (14)
N1—C4—S2—O2A87.10 (15)N11—C14—S12—C12C159.31 (14)
C3—C4—S2—O2A176.01 (14)C13—C14—S12—C12C63.06 (17)
S1—C4—S2—O2A44.44 (14)S11—C14—S12—C12C68.43 (13)
 

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