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In the title compound, C24H38N2O6S2, which was synthesized from (+)-10-camphorsulfonic acid chloride and piperazine, the central piperazine ring adopts a chair conformation. The two camphorlsulfonyl groups are bound to the piperazine N atoms in equatorial positions. The mol­ecule has approximate non-crystallographic twofold symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028595/fl2038sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028595/fl2038Isup2.hkl
Contains datablock I

CCDC reference: 621306

Key indicators

  • Single-crystal X-ray study
  • T = 20 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.124
  • Data-to-parameter ratio = 25.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95 PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.66 Ratio
Alert level C CELLK01_ALERT_1_C Check that the cell measurement temperature is in Kelvin. Value of measurement temperature given = 20.000 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C1A - C2A .. 5.16 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT245_ALERT_2_C U(iso) H9A Smaller than U(eq) C9 by ... 0.02 AngSq PLAT245_ALERT_2_C U(iso) H9B Smaller than U(eq) C9 by ... 0.02 AngSq PLAT245_ALERT_2_C U(iso) H9C Smaller than U(eq) C9 by ... 0.02 AngSq
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 31.25 From the CIF: _reflns_number_total 7818 Count of symmetry unique reflns 4693 Completeness (_total/calc) 166.59% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3125 Fraction of Friedel pairs measured 0.666 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A = . R
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2000); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLEASE SUPPLY; software used to prepare material for publication: CIFTAB (Sheldrick, 1997).

(+)-N,N'-Bis[(7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1- yl)methylsulfonyl]piperazine top
Crystal data top
C24H38N2O6S2F(000) = 1104
Mr = 514.68Dx = 1.335 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac2abCell parameters from 7818 reflections
a = 8.4677 (3) Åθ = 2.4–31.3°
b = 11.1826 (4) ŵ = 0.25 mm1
c = 27.0427 (10) ÅT = 20 K
V = 2560.70 (16) Å3Plate, colorless
Z = 40.34 × 0.33 × 0.25 mm
Data collection top
Oxford Sapphire CCD
diffractometer
7818 independent reflections
Radiation source: fine-focus sealed tube6202 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
θ/2θ scansθmax = 31.3°, θmin = 2.4°
Absorption correction: numerical
(CrysAlis RED; Oxford Diffraction, 2000)
h = 1112
Tmin = 0.920, Tmax = 0.940k = 1514
25421 measured reflectionsl = 3738
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)] = 0.048H-atom parameters constrained
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0664P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
7818 reflectionsΔρmax = 0.31 e Å3
311 parametersΔρmin = 0.28 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (6)
Special details top

Experimental. The IR spectrum was recorded with a Perkin–Elmer Spectrum RX I spectrophotometer. 1H and 13C NMR spectra were taken in CDCl3 with a Varian Gemini 200 spectrometer. 1H NMR (300 MHz, CDCl3): δ 3.50–3.37 [m, 8H, 4CH2 (piperazine)], 3.34 [d, J = 14.7 Hz, 2H, 2CH (CH2S)], 2.76 [d, J = 14.7 Hz, 2H, 2 CH (CH2—S)], 2.53–2.32 [m, 4H, 4 CH (CH2)], 2.11 (t, J = 4.3 Hz, 2H, 2 CH), 2.10–1.99 [m, 2 H, 2 CH (CH2)], 1.94 [d, J = 18.3 Hz, 2H, 2CH (CH2)], 1,64 [ddd, J = 13.8, 9.5, 4.5 Hz, 2H, 2CH (CH2)], 1.44 [ddd, J = 12.6, 9.7, 3.5 Hz, 2H, 2CH (CH2)], 1.11 (s, 6H, 2CH3), 0.87 (s, 6H, 2CH3). 13C NMR (75.5 MHz, CDCl3): δ 214.82 (2CO), 58.11 (2 C), 47.98 (2 C), 45.80 (2CH2S), 45.56 (4CH2N piperazine), 42.72 (2CH), 42.49 (2CH2), 26.86 (2CH2), 25.07 (2CH2), 19.82 (2CH3), 19.70 (2CH3). IR (KBr): 2970, 1734, 1340, 1158, 1089, 946 cm-1.

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
C10.45155 (19)0.96217 (18)0.03633 (6)0.0291 (3)
C20.5882 (3)0.8737 (2)0.04035 (9)0.0476 (5)
O10.5963 (3)0.7907 (2)0.06868 (9)0.0960 (9)
C30.7122 (3)0.9124 (2)0.00377 (9)0.0507 (6)
H3A0.72970.85180.02130.080*
H3B0.81140.93050.02010.080*
C40.6376 (2)1.02441 (18)0.01820 (7)0.0370 (4)
H4A0.71251.07960.03370.080*
C50.5067 (3)0.9805 (3)0.05218 (8)0.0614 (8)
H5A0.54460.91820.07410.080*
H5B0.46411.04550.07180.080*
C60.3810 (3)0.9311 (3)0.01571 (7)0.0601 (7)
H6A0.36810.84540.01960.080*
H6B0.27980.96990.02060.080*
C70.5451 (3)1.07752 (18)0.02588 (8)0.0429 (5)
C80.6540 (4)1.1097 (3)0.06983 (10)0.0795 (10)
H8A0.73271.16580.05910.080*
H8B0.70471.03860.08180.080*
H8C0.59231.14470.09590.080*
C90.4443 (5)1.1843 (2)0.01310 (14)0.0971 (13)
H9A0.51051.24810.00150.080*
H9B0.38781.21010.04200.080*
H9C0.37051.16270.01230.080*
C100.3450 (2)0.9585 (2)0.08180 (7)0.0390 (4)
H10A0.37101.02670.10240.080*
H10B0.37120.88720.10050.080*
S10.13803 (5)0.95912 (5)0.07196 (2)0.03607 (11)
O20.0931 (2)1.06726 (16)0.04861 (6)0.0561 (5)
O30.0961 (2)0.84750 (17)0.04990 (6)0.0582 (5)
N10.05717 (19)0.96053 (15)0.12699 (6)0.0349 (3)
C110.0578 (3)1.07274 (17)0.15558 (7)0.0404 (5)
H11A0.04471.14040.13350.080*
H11B0.15771.08160.17280.080*
C120.0771 (3)1.06899 (17)0.19276 (8)0.0402 (5)
H12A0.07491.13990.21340.080*
H12B0.17761.06650.17560.080*
N1A0.05787 (17)0.96087 (15)0.22346 (5)0.0330 (3)
C130.0744 (3)0.85370 (18)0.15783 (8)0.0431 (5)
H13A0.17470.85590.17510.080*
H13B0.07200.78260.13730.080*
C140.0594 (3)0.85022 (17)0.19464 (8)0.0415 (5)
H14A0.15940.84230.17740.080*
H14B0.04710.78200.21640.080*
S1A0.13407 (5)0.96032 (5)0.27911 (2)0.03266 (11)
O2A0.10310 (19)1.07576 (14)0.29984 (6)0.0484 (4)
O3A0.0741 (2)0.85669 (15)0.30350 (6)0.0536 (4)
C10A0.3407 (2)0.9411 (2)0.27109 (6)0.0354 (4)
H10C0.37680.99980.24730.080*
H10D0.35820.86280.25670.080*
C9A0.6708 (2)1.0663 (2)0.27505 (8)0.0434 (5)
H9D0.61451.09480.24660.080*
H9E0.75641.11970.28240.050*
H9F0.71190.98790.26840.050*
C8A0.4738 (3)1.18064 (19)0.32396 (8)0.0448 (5)
H8D0.40131.17760.35120.050*
H8E0.54991.24280.32960.050*
H8F0.41691.19700.29400.050*
C7A0.5588 (2)1.06051 (16)0.31927 (6)0.0309 (4)
C6A0.3676 (2)0.9519 (2)0.36954 (6)0.0395 (4)
H6C0.33820.87160.37960.080*
H6D0.27451.00250.37020.080*
C5A0.4991 (3)1.0027 (2)0.40339 (7)0.0454 (5)
H5C0.52490.94700.42970.080*
H5D0.46751.07840.41780.080*
C4A0.6385 (3)1.01896 (18)0.36804 (7)0.0370 (4)
H4B0.72141.07250.38030.080*
C3A0.6959 (3)0.8930 (2)0.35443 (8)0.0429 (5)
H3C0.70820.84340.38360.080*
H3D0.79530.89580.33660.080*
C2A0.5631 (3)0.84827 (18)0.32177 (7)0.0364 (4)
O1A0.5511 (2)0.75033 (15)0.30388 (7)0.0611 (5)
C1A0.44445 (19)0.95149 (17)0.31711 (6)0.0265 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0240 (7)0.0340 (8)0.0293 (8)0.0031 (8)0.0029 (6)0.0027 (8)
C20.0479 (13)0.0450 (12)0.0499 (12)0.0089 (10)0.0124 (10)0.0141 (10)
O10.1044 (19)0.0844 (15)0.0992 (16)0.0439 (14)0.0479 (14)0.0525 (13)
C30.0392 (12)0.0600 (14)0.0529 (13)0.0086 (11)0.0121 (10)0.0067 (11)
C40.0357 (9)0.0406 (11)0.0346 (9)0.0054 (9)0.0094 (8)0.0044 (8)
C50.0446 (12)0.108 (2)0.0318 (10)0.0114 (14)0.0057 (9)0.0073 (12)
C60.0423 (12)0.105 (2)0.0335 (10)0.0225 (14)0.0032 (9)0.0125 (12)
C70.0511 (12)0.0298 (9)0.0476 (11)0.0053 (9)0.0197 (10)0.0007 (8)
C80.078 (2)0.094 (2)0.0668 (17)0.0488 (19)0.0234 (16)0.0436 (16)
C90.116 (3)0.0449 (16)0.130 (3)0.0264 (18)0.068 (3)0.0339 (17)
C100.0272 (8)0.0576 (12)0.0323 (8)0.0019 (10)0.0042 (7)0.0095 (9)
S10.0256 (2)0.0472 (3)0.0354 (2)0.0007 (2)0.00547 (17)0.0005 (2)
O20.0509 (10)0.0719 (12)0.0456 (8)0.0209 (9)0.0055 (7)0.0175 (8)
O30.0491 (10)0.0711 (12)0.0544 (10)0.0173 (9)0.0145 (8)0.0242 (8)
N10.0351 (8)0.0311 (7)0.0386 (8)0.0027 (8)0.0136 (6)0.0003 (7)
C110.0498 (12)0.0295 (10)0.0420 (10)0.0035 (9)0.0167 (9)0.0011 (8)
C120.0463 (11)0.0301 (10)0.0441 (10)0.0061 (8)0.0153 (9)0.0008 (8)
N1A0.0305 (7)0.0294 (7)0.0392 (8)0.0017 (7)0.0138 (6)0.0002 (7)
C130.0478 (12)0.0318 (10)0.0496 (12)0.0066 (9)0.0239 (10)0.0020 (8)
C140.0450 (12)0.0299 (10)0.0495 (11)0.0041 (9)0.0226 (10)0.0010 (8)
S1A0.02255 (18)0.0411 (2)0.0344 (2)0.0011 (2)0.00446 (17)0.00071 (19)
O2A0.0488 (9)0.0517 (9)0.0447 (8)0.0173 (7)0.0090 (7)0.0147 (7)
O3A0.0435 (9)0.0662 (11)0.0513 (9)0.0164 (8)0.0088 (7)0.0190 (8)
C10A0.0224 (8)0.0551 (12)0.0288 (8)0.0027 (8)0.0042 (6)0.0083 (8)
C9A0.0328 (10)0.0480 (13)0.0495 (11)0.0054 (9)0.0049 (8)0.0114 (9)
C8A0.0566 (14)0.0304 (10)0.0474 (12)0.0011 (9)0.0059 (10)0.0016 (8)
C7A0.0279 (8)0.0336 (10)0.0312 (8)0.0009 (8)0.0027 (7)0.0039 (7)
C6A0.0353 (9)0.0582 (12)0.0249 (7)0.0085 (11)0.0017 (7)0.0001 (8)
C5A0.0494 (13)0.0600 (13)0.0267 (9)0.0085 (10)0.0074 (8)0.0002 (8)
C4A0.0329 (9)0.0417 (11)0.0363 (9)0.0081 (9)0.0128 (8)0.0027 (7)
C3A0.0350 (10)0.0456 (12)0.0482 (12)0.0002 (9)0.0133 (9)0.0091 (10)
C2A0.0353 (10)0.0372 (10)0.0367 (10)0.0018 (9)0.0053 (8)0.0022 (8)
O1A0.0711 (12)0.0425 (9)0.0698 (11)0.0105 (9)0.0214 (10)0.0152 (8)
C1A0.0221 (7)0.0338 (8)0.0237 (7)0.0009 (8)0.0027 (5)0.0003 (7)
Geometric parameters (Å, º) top
C1—C101.526 (2)C12—H12B0.9700
C1—C21.526 (3)N1A—C141.462 (2)
C1—C71.540 (3)N1A—S1A1.637 (1)
C1—C61.568 (3)C13—C141.509 (3)
C2—O11.206 (3)C13—H13A0.9700
C2—C31.506 (3)C13—H13B0.9700
C3—C41.524 (3)C14—H14A0.9700
C3—H3A0.9700C14—H14B0.9700
C3—H3B0.9700S1A—O3A1.427 (2)
C4—C51.521 (3)S1A—O2A1.432 (2)
C4—C71.545 (3)S1A—C10A1.777 (2)
C4—H4A0.9800C10A—C1A1.528 (2)
C5—C61.553 (3)C10A—H10C0.9700
C5—H5A0.9700C10A—H10D0.9700
C5—H5B0.9700C9A—C7A1.528 (3)
C6—H6A0.9700C9A—H9D0.9600
C6—H6B0.9700C9A—H9E0.9600
C7—C91.508 (4)C9A—H9F0.9600
C7—C81.547 (4)C8A—C7A1.529 (3)
C8—H8A0.9600C8A—H8D0.9600
C8—H8B0.9600C8A—H8E0.9600
C8—H8C0.9600C8A—H8F0.9600
C9—H9A0.9600C7A—C4A1.553 (2)
C9—H9B0.9600C7A—C1A1.558 (3)
C9—H9C0.9600C6A—C5A1.549 (3)
C10—S11.773 (2)C6A—C1A1.560 (2)
C10—H10A0.9700C6A—H6C0.9700
C10—H10B0.9700C6A—H6D0.9700
S1—O21.416 (2)C5A—C4A1.530 (3)
S1—O31.428 (2)C5A—H5C0.9700
S1—N11.638 (2)C5A—H5D0.9700
N1—C131.464 (2)C4A—C3A1.534 (3)
N1—C111.474 (2)C4A—H4B0.9800
C11—C121.523 (3)C3A—C2A1.515 (3)
C11—H11A0.9700C3A—H3C0.9700
C11—H11B0.9700C3A—H3D0.9700
C12—N1A1.476 (2)C2A—O1A1.202 (2)
C12—H12A0.9700C2A—C1A1.536 (3)
C10—C1—C2111.9 (2)C14—N1A—C12113.1 (2)
C10—C1—C7118.4 (2)C14—N1A—S1A118.9 (1)
C2—C1—C799.6 (2)C12—N1A—S1A118.5 (1)
C10—C1—C6119.5 (2)N1—C13—C14108.8 (2)
C2—C1—C6102.1 (2)N1—C13—H13A109.9
C7—C1—C6102.5 (2)C14—C13—H13A109.9
O1—C2—C3126.8 (2)N1—C13—H13B109.9
O1—C2—C1126.0 (2)C14—C13—H13B109.9
C3—C2—C1107.2 (2)H13A—C13—H13B108.3
C2—C3—C4101.7 (2)N1A—C14—C13108.8 (2)
C2—C3—H3A111.4N1A—C14—H14A109.9
C4—C3—H3A111.4C13—C14—H14A109.9
C2—C3—H3B111.4N1A—C14—H14B109.9
C4—C3—H3B111.4C13—C14—H14B109.9
H3A—C3—H3B109.3H14A—C14—H14B108.3
C5—C4—C3105.8 (2)O3A—S1A—O2A119.1 (1)
C5—C4—C7102.8 (2)O3A—S1A—N1A106.74 (9)
C3—C4—C7103.0 (2)O2A—S1A—N1A106.51 (9)
C5—C4—H4A114.6O3A—S1A—C10A108.0 (1)
C3—C4—H4A114.6O2A—S1A—C10A109.7 (1)
C7—C4—H4A114.6N1A—S1A—C10A106.06 (8)
C4—C5—C6103.3 (2)C1A—C10A—S1A117.2 (1)
C4—C5—H5A111.1C1A—C10A—H10C108.0
C6—C5—H5A111.1S1A—C10A—H10C108.0
C4—C5—H5B111.1C1A—C10A—H10D108.0
C6—C5—H5B111.1S1A—C10A—H10D108.0
H5A—C5—H5B109.1H10C—C10A—H10D107.2
C5—C6—C1103.3 (2)C7A—C9A—H9D109.5
C5—C6—H6A111.1C7A—C9A—H9E109.5
C1—C6—H6A111.1H9D—C9A—H9E109.5
C5—C6—H6B111.1C7A—C9A—H9F109.5
C1—C6—H6B111.1H9D—C9A—H9F109.5
H6A—C6—H6B109.1H9E—C9A—H9F109.5
C9—C7—C1114.5 (2)C7A—C8A—H8D109.5
C9—C7—C4114.5 (2)C7A—C8A—H8E109.5
C1—C7—C494.6 (2)H8D—C8A—H8E109.5
C9—C7—C8109.2 (3)C7A—C8A—H8F109.5
C1—C7—C8111.1 (2)H8D—C8A—H8F109.5
C4—C7—C8112.3 (2)H8E—C8A—H8F109.5
C7—C8—H8A109.5C9A—C7A—C8A108.7 (2)
C7—C8—H8B109.5C9A—C7A—C4A114.1 (2)
H8A—C8—H8B109.5C8A—C7A—C4A113.4 (2)
C7—C8—H8C109.5C9A—C7A—C1A112.9 (2)
H8A—C8—H8C109.5C8A—C7A—C1A113.5 (2)
H8B—C8—H8C109.5C4A—C7A—C1A93.9 (1)
C7—C9—H9A109.5C5A—C6A—C1A103.8 (2)
C7—C9—H9B109.5C5A—C6A—H6C111.0
H9A—C9—H9B109.5C1A—C6A—H6C111.0
C7—C9—H9C109.5C5A—C6A—H6D111.0
H9A—C9—H9C109.5C1A—C6A—H6D111.0
H9B—C9—H9C109.5H6C—C6A—H6D109.0
C1—C10—S1117.6 (1)C4A—C5A—C6A103.2 (2)
C1—C10—H10A107.9C4A—C5A—H5C111.1
S1—C10—H10A107.9C6A—C5A—H5C111.1
C1—C10—H10B107.9C4A—C5A—H5D111.1
S1—C10—H10B107.9C6A—C5A—H5D111.1
H10A—C10—H10B107.2H5C—C5A—H5D109.1
O2—S1—O3119.6 (1)C5A—C4A—C3A106.6 (2)
O2—S1—N1106.55 (9)C5A—C4A—C7A103.3 (2)
O3—S1—N1106.5 (1)C3A—C4A—C7A102.1 (2)
O2—S1—C10109.6 (1)C5A—C4A—H4B114.5
O3—S1—C10107.7 (1)C3A—C4A—H4B114.5
N1—S1—C10106.09 (9)C7A—C4A—H4B114.5
C13—N1—C11113.3 (2)C2A—C3A—C4A102.0 (2)
C13—N1—S1117.9 (1)C2A—C3A—H3C111.4
C11—N1—S1118.9 (1)C4A—C3A—H3C111.4
N1—C11—C12108.7 (2)C2A—C3A—H3D111.4
N1—C11—H11A110.0C4A—C3A—H3D111.4
C12—C11—H11A110.0H3C—C3A—H3D109.2
N1—C11—H11B110.0O1A—C2A—C3A126.8 (2)
C12—C11—H11B110.0O1A—C2A—C1A126.6 (2)
H11A—C11—H11B108.3C3A—C2A—C1A106.6 (2)
N1A—C12—C11108.2 (2)C10A—C1A—C2A112.7 (2)
N1A—C12—H12A110.1C10A—C1A—C7A116.6 (2)
C11—C12—H12A110.1C2A—C1A—C7A100.3 (1)
N1A—C12—H12B110.1C10A—C1A—C6A120.1 (1)
C11—C12—H12B110.1C2A—C1A—C6A101.6 (2)
H12A—C12—H12B108.4C7A—C1A—C6A102.9 (1)
C10—C1—C2—O116.8 (4)C11—N1—C13—C1458.9 (2)
C7—C1—C2—O1142.7 (3)S1—N1—C13—C14155.67 (15)
C6—C1—C2—O1112.2 (3)C12—N1A—C14—C1359.9 (2)
C10—C1—C2—C3161.22 (19)S1A—N1A—C14—C13154.26 (15)
C7—C1—C2—C335.3 (2)N1—C13—C14—N1A56.8 (3)
C6—C1—C2—C369.8 (2)C14—N1A—S1A—O3A46.55 (19)
O1—C2—C3—C4176.7 (3)C12—N1A—S1A—O3A169.46 (16)
C1—C2—C3—C41.3 (2)C14—N1A—S1A—O2A174.77 (16)
C2—C3—C4—C574.0 (2)C12—N1A—S1A—O2A41.24 (18)
C2—C3—C4—C733.5 (2)C14—N1A—S1A—C10A68.38 (18)
C3—C4—C5—C670.1 (3)C12—N1A—S1A—C10A75.61 (17)
C7—C4—C5—C637.6 (3)O3A—S1A—C10A—C1A72.71 (18)
C4—C5—C6—C14.2 (3)O2A—S1A—C10A—C1A58.53 (19)
C10—C1—C6—C5163.8 (2)N1A—S1A—C10A—C1A173.20 (15)
C2—C1—C6—C572.2 (2)C1A—C6A—C5A—C4A3.1 (2)
C7—C1—C6—C530.6 (3)C6A—C5A—C4A—C3A70.2 (2)
C10—C1—C7—C966.0 (3)C6A—C5A—C4A—C7A36.9 (2)
C2—C1—C7—C9172.6 (2)C9A—C7A—C4A—C5A171.66 (17)
C6—C1—C7—C967.8 (3)C8A—C7A—C4A—C5A63.2 (2)
C10—C1—C7—C4174.38 (16)C1A—C7A—C4A—C5A54.42 (17)
C2—C1—C7—C452.99 (18)C9A—C7A—C4A—C3A61.2 (2)
C6—C1—C7—C451.8 (2)C8A—C7A—C4A—C3A173.76 (17)
C10—C1—C7—C858.3 (3)C1A—C7A—C4A—C3A56.09 (17)
C2—C1—C7—C863.1 (2)C5A—C4A—C3A—C2A70.88 (19)
C6—C1—C7—C8167.9 (2)C7A—C4A—C3A—C2A37.17 (19)
C5—C4—C7—C964.2 (3)C4A—C3A—C2A—O1A176.1 (2)
C3—C4—C7—C9174.0 (2)C4A—C3A—C2A—C1A2.4 (2)
C5—C4—C7—C155.4 (2)S1A—C10A—C1A—C2A132.03 (16)
C3—C4—C7—C154.42 (19)S1A—C10A—C1A—C7A112.78 (16)
C5—C4—C7—C8170.5 (2)S1A—C10A—C1A—C6A12.5 (3)
C3—C4—C7—C860.7 (2)O1A—C2A—C1A—C10A24.0 (3)
C2—C1—C10—S1135.85 (18)C3A—C2A—C1A—C10A157.48 (16)
C7—C1—C10—S1109.29 (19)O1A—C2A—C1A—C7A148.7 (2)
C6—C1—C10—S116.7 (3)C3A—C2A—C1A—C7A32.81 (18)
C1—C10—S1—O263.0 (2)O1A—C2A—C1A—C6A105.7 (2)
C1—C10—S1—O368.64 (19)C3A—C2A—C1A—C6A72.76 (19)
C1—C10—S1—N1177.63 (16)C9A—C7A—C1A—C10A56.7 (2)
O2—S1—N1—C13175.15 (17)C8A—C7A—C1A—C10A67.5 (2)
O3—S1—N1—C1346.49 (19)C4A—C7A—C1A—C10A174.91 (15)
C10—S1—N1—C1368.10 (19)C9A—C7A—C1A—C2A65.23 (17)
O2—S1—N1—C1141.40 (18)C8A—C7A—C1A—C2A170.56 (16)
O3—S1—N1—C11170.07 (16)C4A—C7A—C1A—C2A52.95 (15)
C10—S1—N1—C1175.34 (18)C9A—C7A—C1A—C6A169.74 (15)
C13—N1—C11—C1258.8 (2)C8A—C7A—C1A—C6A66.06 (19)
S1—N1—C11—C12156.15 (15)C4A—C7A—C1A—C6A51.55 (16)
N1—C11—C12—N1A56.1 (2)C5A—C6A—C1A—C10A162.83 (19)
C11—C12—N1A—C1459.5 (2)C5A—C6A—C1A—C2A72.17 (19)
C11—C12—N1A—S1A154.55 (14)C5A—C6A—C1A—C7A31.3 (2)
 

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