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(1R,3S)-Camphoric acid [(1R,3S)-1,2,2,-trimethylcyclopentane-1,3-dicarboxylic acid, C10H16O4] forms adducts with a range of amines in which the acid component may be the neutral molecule, the mono-anion (C10H15O4) or the di-anion (C10H14O4)2−. The structures generated by the hard hydrogen bonds take the form of chains in the 1:1 adducts (II) and (III) formed with 4,4′-bipyridyl and 1,2-bis(4-pyridyl)­ethane. There are single sheets in the hydrated 1:1 adduct (IV) formed with 1,4-diazabicyclo[2.2.2]octane, and pairwise-interwoven sheets in the 2:1 adduct (V) formed with hexa­methylene­tetramine. Three-dimensional frameworks are present in the salt-like 1:1 adduct (VI) formed with piperazine and in the hydrated 3:1 adduct (VII) formed with N,N′-dimethylpiperazine. This latter adduct contains both neutral C10H16O4 and anionic (C10H15O4) units. In (II), (III) and (IV), the chain and sheet substructures are linked by C—H...O hydrogen bonds to form three-dimensional frameworks. The monoclinic polymorph of camphoric acid itself (I) has been reinvestigated.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102022358/na0144sup1.cif
Contains datablocks global, I, II, III, IV, V, VI, VII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022358/na0144Isup2.hkl
Contains datablock I

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022358/na0144IIsup3.hkl
Contains datablock II

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022358/na0144IIIsup4.hkl
Contains datablock III

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022358/na0144IVsup5.hkl
Contains datablock IV

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022358/na0144Vsup6.hkl
Contains datablock V

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022358/na0144VIsup7.hkl
Contains datablock VI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022358/na0144VIIsup8.hkl
Contains datablock VII

CCDC references: 205190; 205191; 205192; 205193; 205194; 205195; 205196

Computing details top

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999).

(I) (1R,3S)-Camphoric acid top
Crystal data top
C10H16O4F(000) = 432
Mr = 200.23Dx = 1.219 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2608 reflections
a = 7.7206 (3) Åθ = 2.8–27.5°
b = 11.6677 (5) ŵ = 0.09 mm1
c = 12.5830 (5) ÅT = 150 K
β = 105.653 (2)°Needle, colourless
V = 1091.46 (8) Å30.30 × 0.12 × 0.12 mm
Z = 4
Data collection top
Kappa-CCD
diffractometer
2126 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.043
Graphite monochromatorθmax = 27.5°, θmin = 2.8°
φ scans, and ω scans with κ offsetsh = 010
9392 measured reflectionsk = 015
2608 independent reflectionsl = 1615
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.1361P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2608 reflectionsΔρmax = 0.19 e Å3
264 parametersΔρmin = 0.14 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (6)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O110.4517 (2)0.5569 (2)0.08314 (14)0.0471 (5)
O120.7099 (2)0.6090 (2)0.20146 (13)0.0457 (5)
O130.7994 (3)0.5148 (3)0.27972 (18)0.0726 (9)
O141.0477 (2)0.6000 (2)0.18300 (17)0.0584 (6)
C110.6569 (3)0.6756 (2)0.01621 (19)0.0353 (6)
C120.8105 (3)0.6072 (2)0.01901 (18)0.0330 (5)
C130.7780 (3)0.6499 (2)0.14025 (18)0.0354 (6)
C140.5731 (3)0.6496 (3)0.18629 (19)0.0416 (6)
C150.5031 (3)0.6894 (3)0.0909 (2)0.0502 (8)
C160.5949 (3)0.6078 (3)0.10246 (18)0.0358 (6)
C170.7210 (4)0.7945 (3)0.0639 (3)0.0534 (8)
C180.8748 (3)0.5808 (3)0.20740 (19)0.0412 (7)
C190.9998 (3)0.6336 (3)0.0521 (2)0.0467 (7)
C1100.7804 (4)0.4771 (3)0.0168 (2)0.0508 (7)
O210.2139 (2)0.4672 (2)0.70262 (14)0.0493 (6)
O220.0379 (3)0.3933 (3)0.59666 (18)0.0749 (9)
O230.5762 (2)0.4908 (2)0.34303 (14)0.0460 (5)
O240.3219 (2)0.4370 (2)0.22186 (14)0.0459 (5)
C210.2304 (3)0.3461 (2)0.54952 (18)0.0335 (5)
C220.2194 (3)0.4210 (2)0.44317 (17)0.0295 (5)
C230.3740 (3)0.3650 (2)0.40330 (18)0.0315 (5)
C240.5233 (3)0.3405 (3)0.5086 (2)0.0417 (6)
C250.4331 (3)0.3334 (3)0.6028 (2)0.0385 (6)
C260.1367 (3)0.4081 (3)0.62449 (19)0.0403 (6)
C280.4354 (3)0.4370 (2)0.32135 (18)0.0327 (5)
C270.1436 (4)0.2278 (3)0.5199 (2)0.0453 (7)
C290.0376 (3)0.4157 (3)0.3566 (2)0.0451 (7)
C2100.2665 (4)0.5461 (2)0.4745 (2)0.0418 (6)
H120.66570.57340.24590.069*
H141.09400.55840.22240.088*
H130.82060.73100.13820.043*
H14A0.53500.70250.24980.050*
H14B0.52870.57160.21040.050*
H15A0.39810.64270.08680.060*
H15B0.46520.77060.10120.060*
H17A0.62070.83540.08060.080*
H17B0.76440.83830.00980.080*
H17C0.81880.78540.13160.080*
H19A1.00850.61420.12920.070*
H19B1.02530.71530.04660.070*
H19C1.08720.58810.02630.070*
H11A0.86480.43770.05020.076*
H11B0.65680.45890.05850.076*
H11C0.80030.45160.05980.076*
H220.08220.42780.64180.112*
H240.36440.47650.17910.069*
H230.32970.29020.36750.038*
H24A0.61380.40270.52260.050*
H24B0.58410.26730.50150.050*
H25A0.47710.39550.65700.046*
H25B0.45950.25880.64130.046*
H27A0.15250.18410.58770.068*
H27B0.20620.18660.47340.068*
H27C0.01670.23730.47980.068*
H29A0.05760.43920.39010.068*
H29B0.01500.33710.32880.068*
H29C0.03880.46740.29540.068*
H21A0.26850.58980.40830.063*
H21B0.38500.55000.52800.063*
H21C0.17590.57880.50740.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0339 (10)0.0740 (15)0.0329 (9)0.0109 (10)0.0080 (7)0.0054 (9)
O120.0378 (9)0.0706 (14)0.0284 (8)0.0097 (10)0.0085 (7)0.0077 (9)
O130.0372 (11)0.124 (2)0.0628 (13)0.0242 (13)0.0240 (10)0.0523 (15)
O140.0311 (10)0.0863 (17)0.0620 (12)0.0145 (11)0.0196 (9)0.0337 (12)
C110.0279 (12)0.0473 (16)0.0327 (12)0.0042 (11)0.0116 (9)0.0038 (11)
C120.0295 (12)0.0426 (15)0.0299 (11)0.0023 (11)0.0131 (9)0.0038 (10)
C130.0303 (12)0.0466 (16)0.0306 (12)0.0067 (11)0.0104 (9)0.0006 (10)
C140.0312 (12)0.0625 (19)0.0309 (12)0.0054 (13)0.0078 (10)0.0032 (12)
C150.0326 (13)0.085 (2)0.0337 (13)0.0105 (15)0.0110 (10)0.0124 (14)
C160.0288 (12)0.0533 (16)0.0275 (11)0.0039 (12)0.0115 (9)0.0004 (11)
C170.063 (2)0.0463 (18)0.0588 (18)0.0072 (15)0.0294 (15)0.0033 (14)
C180.0291 (12)0.0619 (19)0.0358 (13)0.0122 (13)0.0143 (10)0.0055 (12)
C190.0313 (13)0.071 (2)0.0380 (13)0.0057 (13)0.0089 (11)0.0051 (13)
C1100.0599 (18)0.0429 (17)0.0596 (17)0.0039 (14)0.0335 (15)0.0064 (14)
O210.0323 (9)0.0788 (16)0.0397 (10)0.0101 (10)0.0147 (8)0.0172 (10)
O220.0283 (10)0.137 (3)0.0648 (14)0.0227 (13)0.0223 (9)0.0511 (15)
O230.0334 (9)0.0705 (14)0.0341 (9)0.0141 (10)0.0089 (7)0.0061 (9)
O240.0398 (10)0.0644 (14)0.0326 (9)0.0150 (10)0.0084 (7)0.0046 (9)
C210.0303 (12)0.0415 (15)0.0303 (11)0.0077 (11)0.0108 (9)0.0003 (10)
C220.0261 (11)0.0328 (13)0.0307 (11)0.0001 (10)0.0099 (8)0.0009 (10)
C230.0326 (12)0.0327 (13)0.0329 (11)0.0029 (10)0.0151 (10)0.0009 (10)
C240.0326 (14)0.0516 (17)0.0432 (13)0.0111 (13)0.0138 (11)0.0097 (12)
C250.0309 (13)0.0515 (16)0.0327 (12)0.0003 (12)0.0081 (10)0.0027 (11)
C260.0273 (12)0.0658 (19)0.0297 (11)0.0091 (13)0.0109 (9)0.0028 (12)
C280.0294 (12)0.0418 (14)0.0291 (11)0.0010 (11)0.0117 (9)0.0015 (10)
C270.0470 (16)0.0438 (17)0.0459 (14)0.0133 (13)0.0140 (12)0.0070 (12)
C290.0285 (12)0.066 (2)0.0386 (13)0.0009 (13)0.0056 (10)0.0099 (13)
C2100.0417 (14)0.0333 (14)0.0570 (16)0.0055 (12)0.0244 (12)0.0002 (12)
Geometric parameters (Å, º) top
O11—C161.221 (3)O21—C261.217 (3)
O12—C161.320 (3)O22—C261.309 (3)
O12—H120.84O22—H220.84
O13—C181.214 (3)O23—C281.221 (3)
O14—C181.306 (3)O24—C281.320 (3)
O14—H140.84O24—H240.84
C11—C161.521 (3)C21—C261.518 (3)
C11—C171.538 (4)C21—C251.535 (3)
C11—C151.545 (3)C21—C271.535 (4)
C11—C121.588 (3)C21—C221.581 (3)
C12—C191.525 (4)C22—C291.528 (3)
C12—C1101.538 (4)C22—C2101.530 (4)
C12—C131.559 (3)C22—C231.558 (3)
C13—C181.505 (4)C23—C281.503 (3)
C13—C141.531 (3)C23—C241.530 (4)
C13—H131.00C23—H231.00
C14—C151.516 (4)C24—C251.531 (3)
C14—H14A0.99C24—H24A0.99
C14—H14B0.99C24—H24B0.99
C15—H15A0.99C25—H25A0.99
C15—H15B0.99C25—H25B0.99
C17—H17A0.98C27—H27A0.98
C17—H17B0.98C27—H27B0.98
C17—H17C0.98C27—H27C0.98
C19—H19A0.98C29—H29A0.98
C19—H19B0.98C29—H29B0.98
C19—H19C0.98C29—H29C0.98
C110—H11A0.98C210—H21A0.98
C110—H11B0.98C210—H21B0.98
C110—H11C0.98C210—H21C0.98
C16—O12—H12109.5C26—O22—H22109.5
C18—O14—H14109.5C28—O24—H24109.5
C16—C11—C17108.7 (2)C26—C21—C25112.04 (19)
C16—C11—C15111.1 (2)C26—C21—C27109.2 (2)
C17—C11—C15109.7 (3)C25—C21—C27110.2 (2)
C16—C11—C12109.9 (2)C26—C21—C22109.7 (2)
C17—C11—C12112.1 (2)C25—C21—C22103.83 (17)
C15—C11—C12105.3 (2)C27—C21—C22111.79 (19)
C19—C12—C110108.3 (2)C29—C22—C210109.3 (2)
C19—C12—C13112.7 (2)C29—C22—C23112.94 (19)
C110—C12—C13110.4 (2)C210—C22—C23109.49 (19)
C19—C12—C11113.9 (2)C29—C22—C21114.2 (2)
C110—C12—C11111.3 (2)C210—C22—C21110.74 (19)
C13—C12—C11100.23 (19)C23—C22—C2199.79 (18)
C18—C13—C14113.9 (2)C28—C23—C24113.3 (2)
C18—C13—C12113.9 (2)C28—C23—C22113.4 (2)
C14—C13—C12104.26 (18)C24—C23—C22105.26 (18)
C18—C13—H13108.2C28—C23—H23108.2
C14—C13—H13108.2C24—C23—H23108.2
C12—C13—H13108.2C22—C23—H23108.2
C15—C14—C13104.6 (2)C23—C24—C25106.7 (2)
C15—C14—H14A110.8C23—C24—H24A110.4
C13—C14—H14A110.8C25—C24—H24A110.4
C15—C14—H14B110.8C23—C24—H24B110.4
C13—C14—H14B110.8C25—C24—H24B110.4
H14A—C14—H14B108.9H24A—C24—H24B108.6
C14—C15—C11107.7 (2)C24—C25—C21106.22 (19)
C14—C15—H15A110.2C24—C25—H25A110.5
C11—C15—H15A110.2C21—C25—H25A110.5
C14—C15—H15B110.2C24—C25—H25B110.5
C11—C15—H15B110.2C21—C25—H25B110.5
H15A—C15—H15B108.5H25A—C25—H25B108.7
O11—C16—O12122.4 (2)O21—C26—O22122.4 (2)
O11—C16—C11123.6 (2)O21—C26—C21124.1 (2)
O12—C16—C11114.0 (2)O22—C26—C21113.6 (2)
C11—C17—H17A109.5O23—C28—O24122.4 (2)
C11—C17—H17B109.5O23—C28—C23124.1 (2)
H17A—C17—H17B109.5O24—C28—C23113.5 (2)
C11—C17—H17C109.5C21—C27—H27A109.5
H17A—C17—H17C109.5C21—C27—H27B109.5
H17B—C17—H17C109.5H27A—C27—H27B109.5
O13—C18—O14122.5 (2)C21—C27—H27C109.5
O13—C18—C13123.4 (2)H27A—C27—H27C109.5
O14—C18—C13114.0 (2)H27B—C27—H27C109.5
C12—C19—H19A109.5C22—C29—H29A109.5
C12—C19—H19B109.5C22—C29—H29B109.5
H19A—C19—H19B109.5H29A—C29—H29B109.5
C12—C19—H19C109.5C22—C29—H29C109.5
H19A—C19—H19C109.5H29A—C29—H29C109.5
H19B—C19—H19C109.5H29B—C29—H29C109.5
C12—C110—H11A109.5C22—C210—H21A109.5
C12—C110—H11B109.5C22—C210—H21B109.5
H11A—C110—H11B109.5H21A—C210—H21B109.5
C12—C110—H11C109.5C22—C210—H21C109.5
H11A—C110—H11C109.5H21A—C210—H21C109.5
H11B—C110—H11C109.5H21B—C210—H21C109.5
C16—C11—C12—C1989.0 (3)C26—C21—C22—C2978.2 (3)
C17—C11—C12—C1932.0 (3)C25—C21—C22—C29161.9 (2)
C15—C11—C12—C19151.2 (2)C27—C21—C22—C2943.1 (3)
C16—C11—C12—C11033.8 (3)C26—C21—C22—C21045.8 (3)
C17—C11—C12—C110154.7 (2)C25—C21—C22—C21074.1 (2)
C15—C11—C12—C11086.0 (3)C27—C21—C22—C210167.1 (2)
C16—C11—C12—C13150.5 (2)C26—C21—C22—C23161.06 (19)
C17—C11—C12—C1388.6 (2)C25—C21—C22—C2341.2 (2)
C15—C11—C12—C1330.7 (3)C27—C21—C22—C2377.6 (2)
C19—C12—C13—C1871.9 (3)C29—C22—C23—C2874.7 (3)
C110—C12—C13—C1849.2 (3)C210—C22—C23—C2847.4 (3)
C11—C12—C13—C18166.7 (2)C21—C22—C23—C28163.60 (19)
C19—C12—C13—C14163.3 (2)C29—C22—C23—C24160.9 (2)
C110—C12—C13—C1475.5 (3)C210—C22—C23—C2477.1 (2)
C11—C12—C13—C1441.9 (3)C21—C22—C23—C2439.2 (2)
C18—C13—C14—C15162.5 (3)C28—C23—C24—C25147.5 (2)
C12—C13—C14—C1537.8 (3)C22—C23—C24—C2523.0 (3)
C13—C14—C15—C1117.6 (3)C23—C24—C25—C213.6 (3)
C16—C11—C15—C14127.7 (3)C26—C21—C25—C24146.6 (2)
C17—C11—C15—C14112.0 (3)C27—C21—C25—C2491.5 (3)
C12—C11—C15—C148.8 (3)C22—C21—C25—C2428.3 (3)
C17—C11—C16—O11131.0 (3)C25—C21—C26—O2118.5 (4)
C15—C11—C16—O1110.2 (4)C27—C21—C26—O21140.9 (3)
C12—C11—C16—O11106.0 (3)C22—C21—C26—O2196.2 (3)
C17—C11—C16—O1248.7 (3)C25—C21—C26—O22162.2 (3)
C15—C11—C16—O12169.5 (2)C27—C21—C26—O2239.8 (3)
C12—C11—C16—O1274.3 (3)C22—C21—C26—O2283.1 (3)
C14—C13—C18—O1312.2 (4)C24—C23—C28—O2314.4 (4)
C12—C13—C18—O13107.2 (3)C22—C23—C28—O23105.5 (3)
C14—C13—C18—O14166.2 (3)C24—C23—C28—O24165.5 (2)
C12—C13—C18—O1474.4 (3)C22—C23—C28—O2474.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O230.841.832.670 (2)178
O14—H14···O21i0.841.832.667 (3)175
O22—H22···O13ii0.841.822.657 (3)171
O24—H24···O110.841.802.637 (2)178
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z+1.
(II) (1R,3S)-Camphoric acid–4,4'-bipyridyl (1/1) top
Crystal data top
C10H16O4·C10H8N2Dx = 1.318 Mg m3
Mr = 356.41Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3121Cell parameters from 1103 reflections
Hall symbol: P 31 2"θ = 3.5–26.0°
a = 6.7302 (10) ŵ = 0.09 mm1
c = 34.345 (7) ÅT = 150 K
V = 1347.3 (4) Å3Block, colourless
Z = 30.35 × 0.32 × 0.30 mm
F(000) = 570
Data collection top
Kappa-CCD
diffractometer
889 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.034
Graphite monochromatorθmax = 26.0°, θmin = 3.5°
φ scans, and ω scans with κ offsetsh = 08
4738 measured reflectionsk = 60
1103 independent reflectionsl = 4142
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0528P)2 + 0.131P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1103 reflectionsΔρmax = 0.15 e Å3
164 parametersΔρmin = 0.17 e Å3
14 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (4)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N110.2756 (3)0.8545 (3)0.03353 (6)0.0397 (5)
C120.3888 (5)0.7900 (4)0.05797 (7)0.0439 (7)
C130.5044 (4)0.6790 (4)0.04619 (7)0.0410 (6)
C140.5065 (4)0.6285 (4)0.00682 (7)0.0341 (6)
C150.3904 (4)0.6957 (4)0.01853 (7)0.0379 (6)
C160.2791 (4)0.8076 (4)0.00424 (7)0.0385 (6)
O10.0775 (13)0.987 (3)0.2607 (3)0.0315 (9)0.50
O20.4008 (18)0.814 (3)0.2332 (6)0.0415 (16)0.50
O30.0638 (12)1.0160 (18)0.0781 (3)0.0315 (9)0.50
O40.4268 (18)1.2500 (16)0.1072 (6)0.0415 (16)0.50
C10.0779 (19)1.143 (2)0.1960 (3)0.023 (2)0.50
C20.0694 (7)1.0754 (7)0.16886 (14)0.0259 (11)0.50
C30.116 (2)1.239 (2)0.1333 (3)0.032 (3)0.50
C40.1100 (17)1.2362 (17)0.1263 (3)0.031 (2)0.50
C50.2383 (8)1.1667 (8)0.16558 (11)0.0308 (10)0.50
C60.202 (2)0.971 (2)0.2284 (4)0.0330 (10)0.50
C70.0732 (19)1.3800 (17)0.2158 (3)0.033 (2)0.50
C80.222 (2)1.170 (3)0.1018 (5)0.0330 (10)0.50
C90.2941 (8)1.1174 (9)0.18698 (13)0.0372 (12)0.50
C100.0720 (9)0.8244 (7)0.15685 (13)0.0359 (12)0.50
H120.38940.82270.08490.053*
H130.58180.63730.06470.049*
H150.38690.66520.04560.045*
H160.20190.85310.02220.046*
H3A0.23221.39810.14170.038*0.50
H4A0.20091.12380.10580.037*0.50
H4B0.08081.38970.11820.037*0.50
H5A0.38341.01890.16290.037*0.50
H5B0.27541.28490.17420.037*0.50
H7A0.15561.49660.19580.049*0.50
H7B0.18391.37130.23320.049*0.50
H7C0.02461.42130.23080.049*0.50
H9A0.26091.01570.20940.056*0.50
H9B0.38361.27750.19550.056*0.50
H9C0.38201.08600.16770.056*0.50
H10A0.21810.79570.14570.054*0.50
H10B0.10180.72630.17970.054*0.50
H10C0.01290.78970.13740.054*0.50
H10.16160.82870.27520.040*0.50
H30.16160.99030.05810.040*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0343 (12)0.0318 (12)0.0499 (13)0.0141 (10)0.0106 (10)0.0006 (10)
C120.0523 (17)0.0384 (14)0.0426 (14)0.0238 (13)0.0161 (12)0.0056 (12)
C130.0431 (15)0.0371 (14)0.0453 (14)0.0220 (12)0.0091 (12)0.0039 (12)
C140.0238 (12)0.0237 (12)0.0466 (14)0.0058 (10)0.0058 (10)0.0035 (10)
C150.0289 (13)0.0339 (13)0.0455 (14)0.0117 (11)0.0033 (11)0.0120 (11)
C160.0293 (13)0.0339 (14)0.0492 (14)0.0134 (12)0.0028 (11)0.0059 (12)
O10.0303 (11)0.028 (4)0.040 (3)0.0167 (13)0.0034 (13)0.0028 (13)
O20.019 (2)0.044 (2)0.053 (6)0.010 (2)0.008 (3)0.001 (3)
O30.0303 (11)0.028 (4)0.040 (3)0.0167 (13)0.0034 (13)0.0028 (13)
O40.019 (2)0.044 (2)0.053 (6)0.010 (2)0.008 (3)0.001 (3)
C10.023 (4)0.025 (5)0.025 (4)0.016 (4)0.002 (3)0.005 (3)
C20.027 (3)0.027 (2)0.023 (2)0.013 (2)0.000 (3)0.001 (2)
C30.030 (5)0.028 (5)0.037 (5)0.014 (4)0.003 (4)0.007 (4)
C40.034 (4)0.036 (6)0.028 (4)0.021 (4)0.002 (3)0.005 (3)
C50.027 (2)0.029 (3)0.039 (3)0.016 (2)0.002 (2)0.001 (2)
C60.024 (2)0.029 (4)0.044 (2)0.012 (4)0.0007 (19)0.010 (4)
C70.032 (4)0.025 (4)0.036 (5)0.010 (3)0.009 (3)0.003 (3)
C80.024 (2)0.029 (4)0.044 (2)0.012 (4)0.0007 (19)0.010 (4)
C90.030 (3)0.054 (3)0.034 (3)0.026 (2)0.005 (2)0.000 (2)
C100.051 (4)0.030 (3)0.031 (3)0.023 (3)0.002 (2)0.003 (2)
Geometric parameters (Å, º) top
N11—C161.338 (3)C2—C101.524 (5)
N11—C121.343 (3)C2—C91.525 (5)
C12—C131.382 (3)C2—C31.568 (8)
C12—H120.95C3—C81.494 (8)
C13—C141.396 (3)C3—C41.529 (9)
C13—H130.95C3—H3A1.00
C14—C151.388 (3)C4—C51.541 (8)
C14—C14i1.498 (4)C4—H4A0.99
C15—C161.391 (3)C4—H4B0.99
C15—H150.95C5—H5A0.99
C16—H160.95C5—H5B0.99
O1—C61.363 (8)C7—H7A0.98
O1—H11.0471C7—H7B0.98
O2—C61.231 (8)C7—H7C0.98
O3—C81.327 (8)C9—H9A0.98
O3—H31.0249C9—H9B0.98
O4—C81.219 (9)C9—H9C0.98
C1—C61.523 (8)C10—H10A0.98
C1—C71.552 (8)C10—H10B0.98
C1—C51.566 (10)C10—H10C0.98
C1—C21.586 (9)
C16—N11—C12116.8 (2)C3—C4—C5105.6 (7)
N11—C12—C13123.7 (2)C3—C4—H4A110.6
N11—C12—H12118.1C5—C4—H4A110.6
C13—C12—H12118.1C3—C4—H4B110.6
C12—C13—C14119.5 (2)C5—C4—H4B110.6
C12—C13—H13120.3H4A—C4—H4B108.7
C14—C13—H13120.3C4—C5—C1107.7 (7)
C15—C14—C13116.9 (2)C4—C5—H5A110.2
C15—C14—C14i122.3 (3)C1—C5—H5A110.2
C13—C14—C14i120.8 (3)C4—C5—H5B110.2
C14—C15—C16119.9 (2)C1—C5—H5B110.2
C14—C15—H15120.1H5A—C5—H5B108.5
C16—C15—H15120.1O2—C6—O1108.7 (14)
N11—C16—C15123.2 (2)O2—C6—C1134.3 (11)
N11—C16—H16118.4O1—C6—C1116.9 (13)
C15—C16—H16118.4C1—C7—H7A109.5
C6—O1—H1107.9C1—C7—H7B109.5
C8—O3—H3102.2H7A—C7—H7B109.5
C6—C1—C7107.0 (8)C1—C7—H7C109.5
C6—C1—C5114.9 (9)H7A—C7—H7C109.5
C7—C1—C5108.7 (9)H7B—C7—H7C109.5
C6—C1—C2113.2 (11)O4—C8—O3136.6 (11)
C7—C1—C2111.7 (7)O4—C8—C3111.2 (10)
C5—C1—C2101.5 (6)O3—C8—C3111.6 (14)
C10—C2—C9109.2 (4)C2—C9—H9A109.5
C10—C2—C3111.3 (6)C2—C9—H9B109.5
C9—C2—C3110.9 (6)H9A—C9—H9B109.5
C10—C2—C1110.2 (5)C2—C9—H9C109.5
C9—C2—C1114.3 (5)H9A—C9—H9C109.5
C3—C2—C1100.8 (4)H9B—C9—H9C109.5
C8—C3—C4120.5 (9)C2—C10—H10A109.5
C8—C3—C2107.5 (12)C2—C10—H10B109.5
C4—C3—C2105.4 (7)H10A—C10—H10B109.5
C8—C3—H3A107.6C2—C10—H10C109.5
C4—C3—H3A107.6H10A—C10—H10C109.5
C2—C3—H3A107.6H10B—C10—H10C109.5
C16—N11—C12—C130.5 (3)C10—C2—C3—C475.8 (9)
N11—C12—C13—C140.0 (4)C9—C2—C3—C4162.5 (7)
C12—C13—C14—C150.3 (3)C1—C2—C3—C441.1 (10)
C12—C13—C14—C14i179.46 (16)C8—C3—C4—C5145.5 (12)
C13—C14—C15—C160.0 (3)C2—C3—C4—C523.9 (11)
C14i—C14—C15—C16179.72 (14)C3—C4—C5—C13.2 (11)
C12—N11—C16—C150.7 (3)C6—C1—C5—C4150.7 (10)
C14—C15—C16—N110.5 (3)C7—C1—C5—C489.6 (7)
C6—C1—C2—C1047.3 (9)C2—C1—C5—C428.2 (9)
C7—C1—C2—C10168.1 (7)C7—C1—C6—O2136 (2)
C5—C1—C2—C1076.3 (7)C5—C1—C6—O215 (3)
C6—C1—C2—C976.0 (9)C2—C1—C6—O2101 (3)
C7—C1—C2—C944.8 (10)C7—C1—C6—O142.3 (18)
C5—C1—C2—C9160.4 (5)C5—C1—C6—O1163.0 (11)
C6—C1—C2—C3165.0 (6)C2—C1—C6—O181.2 (16)
C7—C1—C2—C374.2 (11)C4—C3—C8—O4157.9 (15)
C5—C1—C2—C341.4 (9)C2—C3—C8—O481 (2)
C10—C2—C3—C854.0 (9)C4—C3—C8—O330 (2)
C9—C2—C3—C867.8 (10)C2—C3—C8—O391.1 (15)
C1—C2—C3—C8170.8 (7)
Symmetry code: (i) y, x, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N11ii1.051.692.732 (16)175
O3—H3···N111.021.682.666 (10)159
C15—H15···O2iii0.952.443.293 (19)149
C15—H15···O4iv0.952.533.425 (19)156
Symmetry codes: (ii) x, x+y, z+1/3; (iii) x+y1, x, z1/3; (iv) y1, x, z.
(III) (1R,3S)-Camphoric acid–1,2-bis(4-pyridyl)ethane (1/1) top
Crystal data top
C12H12N2·C10H16O4Z = 4
Mr = 384.46F(000) = 824
Triclinic, P1Dx = 1.258 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5318 (2) ÅCell parameters from 9230 reflections
b = 10.3775 (2) Åθ = 2.6–27.4°
c = 23.3884 (5) ŵ = 0.09 mm1
α = 99.8190 (8)°T = 150 K
β = 95.4780 (8)°Block, colourless
γ = 90.7870 (9)°0.36 × 0.28 × 0.18 mm
V = 2030.17 (8) Å3
Data collection top
Kappa-CCD
diffractometer
7063 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.064
Graphite monochromatorθmax = 27.4°, θmin = 2.6°
φ scans, and ω scans with κ offsetsh = 011
34201 measured reflectionsk = 1313
9230 independent reflectionsl = 3029
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0763P)2 + 0.2326P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
9230 reflectionsΔρmax = 0.26 e Å3
1272 parametersΔρmin = 0.20 e Å3
241 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (4)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A1.9906 (4)1.0925 (4)1.12261 (14)0.0530 (9)0.8469 (14)
O2A1.8735 (4)0.9515 (3)1.16787 (14)0.0417 (7)0.8469 (14)
O3A2.1254 (10)1.2821 (5)1.3935 (3)0.0418 (12)0.8469 (14)
O4A2.2848 (10)1.3950 (4)1.3481 (2)0.0362 (12)0.8469 (14)
C1A2.1204 (4)1.0486 (4)1.21304 (15)0.0297 (8)0.8469 (14)
C2A2.1244 (5)1.1915 (4)1.24833 (17)0.0332 (9)0.8469 (14)
C3A2.2298 (6)1.1757 (4)1.30526 (18)0.0308 (9)0.8469 (14)
C4A2.1864 (6)1.0391 (5)1.3176 (3)0.0409 (12)0.8469 (14)
C5A2.1005 (5)0.9642 (4)1.26064 (17)0.0404 (9)0.8469 (14)
C6A1.9906 (5)1.0328 (4)1.16321 (17)0.0345 (9)0.8469 (14)
C7A2.2761 (5)1.0161 (4)1.18631 (18)0.0456 (10)0.8469 (14)
C8A2.2073 (6)1.2870 (4)1.35438 (18)0.0294 (9)0.8469 (14)
C9A1.9575 (5)1.2298 (5)1.2627 (2)0.0462 (11)0.8469 (14)
C10A2.1911 (6)1.2946 (4)1.2169 (2)0.0468 (11)0.8469 (14)
O1U2.129 (6)1.259 (4)1.3922 (14)0.0425 (9)*0.1531 (14)
O2U2.287 (6)1.378 (3)1.3552 (18)0.0425 (9)*0.1531 (14)
O3U2.1814 (19)1.1454 (16)1.1087 (6)0.0425 (9)*0.1531 (14)
O4U1.9840 (18)1.0191 (19)1.1232 (8)0.0425 (9)*0.1531 (14)
C1U2.231 (2)1.159 (2)1.3029 (8)0.0425 (9)*0.1531 (14)
C2U2.109 (2)1.165 (2)1.2493 (8)0.0425 (9)*0.1531 (14)
C3U2.1893 (19)1.073 (2)1.2016 (6)0.0425 (9)*0.1531 (14)
C4U2.367 (2)1.111 (2)1.2123 (7)0.0425 (9)*0.1531 (14)
C5U2.395 (2)1.167 (2)1.2782 (8)0.0425 (9)*0.1531 (14)
C6U2.210 (4)1.266 (3)1.3527 (7)0.0425 (9)*0.1531 (14)
C7U2.220 (4)1.029 (3)1.3255 (17)0.0425 (9)*0.1531 (14)
C8U2.1192 (18)1.0851 (16)1.1415 (6)0.0425 (9)*0.1531 (14)
C9U2.094 (3)1.303 (2)1.2328 (11)0.0425 (9)*0.1531 (14)
C10U1.940 (2)1.114 (2)1.2567 (11)0.0425 (9)*0.1531 (14)
N1B1.6234 (4)0.9914 (3)1.09700 (15)0.0357 (7)0.8469 (14)
C12B1.6029 (5)1.1194 (4)1.0986 (2)0.0405 (10)0.8469 (14)
C13B1.4718 (5)1.1702 (4)1.0725 (2)0.0386 (10)0.8469 (14)
C14B1.3513 (5)1.0861 (4)1.04244 (17)0.0335 (8)0.8469 (14)
C15B1.3730 (5)0.9530 (4)1.04047 (17)0.0331 (8)0.8469 (14)
C16B1.5081 (5)0.9098 (4)1.06798 (17)0.0355 (9)0.8469 (14)
C17B1.2006 (5)1.1317 (4)1.01468 (18)0.0360 (9)0.8469 (14)
N2B0.7449 (4)1.3958 (3)0.94272 (14)0.0314 (7)0.8469 (14)
C22B0.7681 (5)1.3986 (4)1.00028 (18)0.0371 (9)0.8469 (14)
C23B0.9056 (5)1.3589 (4)1.02788 (18)0.0370 (9)0.8469 (14)
C24B1.0288 (5)1.3170 (4)0.99547 (18)0.0343 (9)0.8469 (14)
C25B1.0047 (5)1.3112 (4)0.93530 (19)0.0352 (9)0.8469 (14)
C26B0.8638 (5)1.3512 (4)0.91135 (18)0.0355 (9)0.8469 (14)
C27B1.1846 (5)1.2781 (4)1.0230 (2)0.0449 (11)0.8469 (14)
N1V0.929 (2)1.5250 (15)0.8848 (8)0.0425 (9)*0.1531 (14)
C12V0.944 (2)1.3958 (17)0.8834 (8)0.0425 (9)*0.1531 (14)
C13V1.074 (2)1.343 (2)0.9104 (8)0.0425 (9)*0.1531 (14)
C14V1.196 (2)1.4242 (17)0.9397 (9)0.0425 (9)*0.1531 (14)
C15V1.177 (2)1.5572 (18)0.9400 (10)0.0425 (9)*0.1531 (14)
C16V1.042 (2)1.607 (2)0.9148 (9)0.0425 (9)*0.1531 (14)
C17V1.338 (2)1.3762 (18)0.9718 (10)0.0425 (9)*0.1531 (14)
N2V1.781 (2)1.1136 (19)1.0498 (7)0.0425 (9)*0.1531 (14)
C22V1.663 (2)1.1569 (19)1.0816 (10)0.0425 (9)*0.1531 (14)
C23V1.520 (2)1.197 (2)1.0573 (8)0.0425 (9)*0.1531 (14)
C24V1.502 (2)1.193 (2)0.9973 (8)0.0425 (9)*0.1531 (14)
C25V1.628 (2)1.151 (2)0.9658 (9)0.0425 (9)*0.1531 (14)
C26V1.764 (2)1.107 (2)0.9915 (8)0.0425 (9)*0.1531 (14)
C27V1.353 (2)1.2305 (18)0.9658 (10)0.0425 (9)*0.1531 (14)
O1C0.5413 (3)1.4813 (3)0.86825 (14)0.0362 (7)0.8469 (14)
O2C0.3453 (3)1.3568 (3)0.88713 (13)0.0369 (6)0.8469 (14)
O3C0.2151 (10)1.1182 (5)0.6520 (4)0.0335 (10)0.8469 (14)
O4C0.3843 (11)1.2246 (8)0.6085 (3)0.0447 (12)0.8469 (14)
C1C0.3259 (4)1.4346 (3)0.79467 (15)0.0275 (8)0.8469 (14)
C2C0.4070 (5)1.3468 (3)0.74518 (17)0.0260 (8)0.8469 (14)
C3C0.2767 (6)1.3420 (4)0.6922 (2)0.0290 (8)0.8469 (14)
C4C0.1168 (6)1.3566 (5)0.7176 (3)0.0324 (12)0.8469 (14)
C5C0.1537 (4)1.3816 (4)0.78379 (16)0.0313 (8)0.8469 (14)
C6C0.4024 (4)1.4194 (4)0.85476 (15)0.0282 (8)0.8469 (14)
C7C0.3319 (5)1.5801 (3)0.78932 (17)0.0389 (9)0.8469 (14)
C8C0.2962 (6)1.2231 (5)0.64648 (18)0.0290 (9)0.8469 (14)
C9C0.4371 (5)1.2109 (4)0.76067 (17)0.0319 (8)0.8469 (14)
C10C0.5635 (5)1.4039 (4)0.73215 (18)0.0406 (10)0.8469 (14)
O1W0.196 (7)1.118 (3)0.654 (3)0.0425 (9)*0.1531 (14)
O2W0.372 (7)1.212 (5)0.6104 (16)0.0425 (9)*0.1531 (14)
O3W0.6568 (17)1.5624 (16)0.8241 (7)0.0425 (9)*0.1531 (14)
O4W0.567 (2)1.4222 (18)0.8731 (6)0.0425 (9)*0.1531 (14)
C1W0.281 (3)1.3378 (18)0.6967 (10)0.0425 (9)*0.1531 (14)
C2W0.399 (2)1.3246 (18)0.7507 (9)0.0425 (9)*0.1531 (14)
C3W0.4018 (19)1.4635 (17)0.7891 (7)0.0425 (9)*0.1531 (14)
C4W0.383 (3)1.5580 (16)0.7446 (7)0.0425 (9)*0.1531 (14)
C5W0.318 (3)1.478 (2)0.6850 (7)0.0425 (9)*0.1531 (14)
C6W0.288 (4)1.219 (3)0.6502 (10)0.0425 (9)*0.1531 (14)
C7W0.111 (3)1.335 (4)0.713 (2)0.0425 (9)*0.1531 (14)
C8W0.5451 (19)1.4811 (16)0.8329 (7)0.0425 (9)*0.1531 (14)
C9W0.563 (2)1.298 (2)0.7284 (10)0.0425 (9)*0.1531 (14)
C10W0.361 (3)1.212 (2)0.7844 (10)0.0425 (9)*0.1531 (14)
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C15D0.5197 (4)0.8078 (3)0.53341 (15)0.0332 (7)
C16D0.4458 (4)0.9144 (3)0.56219 (15)0.0358 (8)
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C22D0.7398 (4)0.2157 (3)0.41099 (14)0.0329 (7)
C23D0.6732 (4)0.3286 (3)0.43886 (14)0.0303 (7)
C24D0.5392 (4)0.3172 (3)0.46712 (13)0.0275 (7)
C25D0.4779 (4)0.1920 (3)0.46500 (16)0.0359 (8)
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C3E0.6812 (5)0.4331 (4)0.20125 (16)0.0345 (9)0.8469 (14)
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C7E0.6983 (7)0.4659 (5)0.33044 (18)0.0407 (10)0.8469 (14)
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C3X0.730 (4)0.326 (2)0.3050 (10)0.0425 (9)*0.1531 (14)
C4X0.696 (5)0.468 (3)0.3137 (9)0.0425 (9)*0.1531 (14)
C5X0.600 (2)0.5354 (19)0.2567 (8)0.0425 (9)*0.1531 (14)
C6X0.4950 (19)0.4643 (15)0.1607 (6)0.0425 (9)*0.1531 (14)
C7X0.783 (2)0.487 (2)0.1849 (9)0.0425 (9)*0.1531 (14)
C8X0.701 (4)0.211 (3)0.3522 (9)0.0425 (9)*0.1531 (14)
C9X0.461 (2)0.267 (2)0.2605 (10)0.0425 (9)*0.1531 (14)
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C12F0.1585 (6)0.3463 (4)0.08117 (19)0.0394 (10)0.8469 (14)
C13F0.0170 (6)0.3071 (5)0.0568 (2)0.0396 (10)0.8469 (14)
C14F0.0052 (5)0.3124 (4)0.00306 (18)0.0333 (8)0.8469 (14)
C15F0.1183 (5)0.3546 (4)0.03497 (18)0.0374 (9)0.8469 (14)
C16F0.2563 (5)0.3928 (4)0.00668 (18)0.0392 (9)0.8469 (14)
C17F0.1585 (5)0.2728 (4)0.0320 (2)0.0400 (10)0.8469 (14)
C22F0.5649 (5)0.1068 (4)0.11249 (19)0.0403 (10)0.8469 (14)
C23F0.4346 (5)0.1605 (4)0.08679 (19)0.0358 (9)0.8469 (14)
C24F0.3124 (4)0.0785 (4)0.05744 (15)0.0281 (7)0.8469 (14)
C25F0.3288 (5)0.0542 (4)0.05718 (18)0.0354 (9)0.8469 (14)
C26F0.4631 (5)0.1000 (4)0.08404 (18)0.0367 (9)0.8469 (14)
C27F0.1671 (4)0.1266 (4)0.02665 (17)0.0299 (8)0.8469 (14)
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C13Y0.485 (3)0.186 (2)0.0656 (8)0.0425 (9)*0.1531 (14)
C14Y0.460 (2)0.179 (2)0.0056 (8)0.0425 (9)*0.1531 (14)
C15Y0.583 (2)0.135 (2)0.0265 (9)0.0425 (9)*0.1531 (14)
C16Y0.723 (2)0.098 (2)0.0006 (8)0.0425 (9)*0.1531 (14)
C17Y0.305 (2)0.2201 (18)0.0201 (10)0.0425 (9)*0.1531 (14)
N2Y0.132 (2)0.5057 (16)0.0945 (8)0.0425 (9)*0.1531 (14)
C22Y0.116 (3)0.3764 (19)0.0952 (10)0.0425 (9)*0.1531 (14)
C23Y0.019 (2)0.327 (3)0.0691 (10)0.0425 (9)*0.1531 (14)
C24Y0.142 (2)0.4119 (18)0.0415 (10)0.0425 (9)*0.1531 (14)
C25Y0.122 (2)0.5460 (19)0.0373 (9)0.0425 (9)*0.1531 (14)
C26Y0.012 (2)0.586 (2)0.0676 (9)0.0425 (9)*0.1531 (14)
C27Y0.292 (2)0.3667 (18)0.0130 (10)0.0425 (9)*0.1531 (14)
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O3G0.8481 (3)0.0623 (3)0.17325 (13)0.0367 (6)0.8469 (14)
O4G0.9431 (4)0.0806 (4)0.12303 (14)0.0515 (9)0.8469 (14)
C1G1.2334 (4)0.1572 (4)0.29768 (16)0.0261 (9)0.8469 (14)
C2G1.1072 (4)0.1744 (3)0.24584 (16)0.0270 (8)0.8469 (14)
C3G1.1037 (4)0.0367 (4)0.20677 (15)0.0298 (8)0.8469 (14)
C4G1.1229 (5)0.0609 (4)0.24922 (17)0.0371 (9)0.8469 (14)
C5G1.1908 (5)0.0186 (3)0.30878 (16)0.0323 (8)0.8469 (14)
C6G1.2150 (6)0.2653 (4)0.34925 (16)0.0272 (9)0.8469 (14)
C7G1.4028 (5)0.1582 (8)0.27979 (19)0.0342 (11)0.8469 (14)
C8G0.9580 (4)0.0188 (4)0.16335 (17)0.0325 (8)0.8469 (14)
C9G0.9455 (4)0.2002 (4)0.26872 (17)0.0340 (8)0.8469 (14)
C10G1.1471 (5)0.2846 (4)0.21297 (18)0.0390 (9)0.8469 (14)
O1Z0.9487 (19)0.018 (2)0.1306 (9)0.0425 (9)*0.1531 (14)
O2Z1.146 (2)0.1403 (16)0.1133 (6)0.0425 (9)*0.1531 (14)
O3Z1.274 (7)0.364 (3)0.3489 (19)0.0425 (9)*0.1531 (14)
O4Z1.132 (6)0.245 (4)0.3978 (12)0.0425 (9)*0.1531 (14)
C1Z1.1661 (19)0.0602 (17)0.2045 (6)0.0425 (9)*0.1531 (14)
C2Z1.086 (2)0.1459 (18)0.2546 (8)0.0425 (9)*0.1531 (14)
C3Z1.214 (3)0.139 (3)0.3066 (8)0.0425 (9)*0.1531 (14)
C4Z1.375 (3)0.146 (6)0.2827 (9)0.0425 (9)*0.1531 (14)
C5Z1.341 (2)0.113 (2)0.2155 (8)0.0425 (9)*0.1531 (14)
C6Z1.0896 (19)0.0754 (17)0.1454 (6)0.0425 (9)*0.1531 (14)
C7Z1.167 (3)0.0850 (16)0.2110 (10)0.0425 (9)*0.1531 (14)
C8Z1.202 (4)0.254 (3)0.3554 (7)0.0425 (9)*0.1531 (14)
C9Z1.051 (3)0.2850 (18)0.2414 (11)0.0425 (9)*0.1531 (14)
C10Z0.931 (2)0.086 (2)0.2713 (10)0.0425 (9)*0.1531 (14)
N1H1.1782 (3)0.5864 (3)0.40893 (11)0.0310 (6)
N2H0.8214 (3)1.3975 (3)0.58706 (12)0.0323 (6)
C12H1.2375 (4)0.7066 (3)0.41000 (14)0.0331 (7)
C13H1.1707 (4)0.8189 (3)0.43655 (13)0.0296 (7)
C14H1.0362 (4)0.8105 (3)0.46476 (13)0.0276 (7)
C15H0.9732 (4)0.6848 (3)0.46316 (15)0.0336 (7)
C16H1.0465 (4)0.5777 (3)0.43505 (15)0.0347 (7)
C17H0.9583 (4)0.9267 (3)0.49657 (14)0.0289 (7)
C22H0.7649 (4)1.2772 (3)0.58853 (14)0.0333 (7)
C23H0.8326 (4)1.1646 (3)0.56088 (14)0.0325 (7)
C24H0.9619 (4)1.1750 (3)0.53023 (13)0.0280 (7)
C25H1.0196 (4)1.3012 (3)0.52919 (15)0.0334 (7)
C26H0.9476 (4)1.4076 (3)0.55794 (15)0.0350 (8)
C27H1.0403 (4)1.0589 (3)0.49781 (14)0.0305 (7)
H2A1.79750.96021.14330.063*0.8469 (14)
H4A2.25281.45951.37030.054*0.8469 (14)
H3A2.34271.17681.29710.037*0.8469 (14)
H4A12.28250.99341.32900.049*0.8469 (14)
H4A22.11701.04651.34950.049*0.8469 (14)
H5A11.98750.95101.26510.048*0.8469 (14)
H5A22.14700.87761.25000.048*0.8469 (14)
H7A12.36291.02481.21750.068*0.8469 (14)
H7A22.29511.07671.15960.068*0.8469 (14)
H7A32.26950.92621.16480.068*0.8469 (14)
H9A11.91301.16461.28290.069*0.8469 (14)
H9A21.89081.23341.22660.069*0.8469 (14)
H9A31.96211.31581.28790.069*0.8469 (14)
H10A2.29781.27171.20750.070*0.8469 (14)
H10B2.19461.38041.24230.070*0.8469 (14)
H10C2.12371.29801.18090.070*0.8469 (14)
H2U2.25361.44781.37310.064*0.15
H4U1.91951.04921.09980.064*0.15
H3U2.17430.98021.20730.051*0.1531 (14)
H4U12.39361.17691.18870.051*0.1531 (14)
H4U22.43151.03301.20240.051*0.1531 (14)
H5U12.43441.25901.28430.051*0.1531 (14)
H5U22.47241.11521.29790.051*0.1531 (14)
H7U12.23460.95681.29390.064*0.1531 (14)
H7U22.11541.02001.33900.064*0.1531 (14)
H7U32.30111.02871.35790.064*0.1531 (14)
H9U12.04281.36041.26280.064*0.1531 (14)
H9U22.03101.29691.19510.064*0.1531 (14)
H9U32.19931.33971.23000.064*0.1531 (14)
H10D1.89671.17331.28820.064*0.1531 (14)
H10E1.94591.02621.26630.064*0.1531 (14)
H10F1.87281.11221.22020.064*0.1531 (14)
H12B1.68341.17871.11890.049*0.8469 (14)
H13B1.46361.26221.07500.046*0.8469 (14)
H15B1.29480.89151.02020.040*0.8469 (14)
H16B1.51970.81831.06620.043*0.8469 (14)
H17E1.11111.09371.03090.043*0.8469 (14)
H17F1.19221.09690.97230.043*0.8469 (14)
H22B0.68631.42941.02340.045*0.8469 (14)
H23B0.91531.36051.06880.044*0.8469 (14)
H25B1.08431.28010.91110.042*0.8469 (14)
H26B0.84951.34720.87030.043*0.8469 (14)
H27E1.27131.31681.00550.054*0.8469 (14)
H27F1.19481.31421.06520.054*0.8469 (14)
H12V0.86211.33810.86290.051*0.1531 (14)
H13V1.07881.25060.90880.051*0.1531 (14)
H15V1.26031.61650.95820.051*0.1531 (14)
H16V1.03041.69930.91880.051*0.1531 (14)
H17I1.33701.41261.01380.051*0.1531 (14)
H17J1.43281.41260.95850.051*0.1531 (14)
H22V1.67791.16011.12260.051*0.1531 (14)
H23V1.43891.22661.08090.051*0.1531 (14)
H25V1.61911.15290.92510.051*0.1531 (14)
H26V1.84541.07340.96860.051*0.1531 (14)
H27I1.26171.19320.98130.051*0.1531 (14)
H27J1.35001.19220.92390.051*0.1531 (14)
H1C0.59121.45170.89570.054*0.8469 (14)
H3C0.24651.05280.63020.050*0.8469 (14)
H3C10.29471.42090.67410.035*0.8469 (14)
H4C10.05991.43080.70480.039*0.8469 (14)
H4C20.05061.27590.70470.039*0.8469 (14)
H5C10.14261.29960.79950.038*0.8469 (14)
H5C20.08201.44660.80240.038*0.8469 (14)
H7C10.28301.59090.75080.058*0.8469 (14)
H7C20.44181.61200.79410.058*0.8469 (14)
H7C30.27461.63040.81970.058*0.8469 (14)
H9C10.33821.17240.76920.048*0.8469 (14)
H9C20.51431.21890.79500.048*0.8469 (14)
H9C30.47801.15460.72770.048*0.8469 (14)
H10G0.54691.49070.72180.061*0.8469 (14)
H10H0.60401.34620.69950.061*0.8469 (14)
H10I0.63981.41150.76670.061*0.8469 (14)
H1W0.23351.05200.63460.064*0.15
H3W0.74251.55070.84320.064*0.15
H3W10.30621.46970.81090.051*0.1531 (14)
H4W10.31051.62790.75750.051*0.1531 (14)
H4W20.48691.59920.74140.051*0.1531 (14)
H5W10.39661.47590.65640.051*0.1531 (14)
H5W20.22091.51760.66970.051*0.1531 (14)
H7W10.09561.41040.74340.064*0.1531 (14)
H7W20.09111.25400.72850.064*0.1531 (14)
H7W30.03681.33730.67880.064*0.1531 (14)
H9W10.56111.21200.70360.064*0.1531 (14)
H9W20.64291.30120.76170.064*0.1531 (14)
H9W30.58941.36550.70570.064*0.1531 (14)
H10J0.25921.22630.80000.064*0.1531 (14)
H10K0.44351.21130.81670.064*0.1531 (14)
H10L0.35781.12790.75780.064*0.1531 (14)
H12D0.17180.77260.61050.041*
H13D0.28820.58760.56620.039*
H15D0.60950.82050.51370.040*
H16D0.48760.99950.56180.043*
H17C0.64980.56380.51970.035*
H17D0.54640.57900.46070.035*
H22D0.83220.22510.39220.039*
H23D0.71910.41230.43850.036*
H25D0.38560.17950.48330.043*
H26D0.50610.00130.43590.041*
H27C0.45490.41880.54060.037*
H27D0.35030.43470.48200.037*
H2E0.75700.05460.36850.053*0.8469 (14)
H4E0.42930.45410.09720.070*0.8469 (14)
H3E0.66300.52530.20690.041*0.8469 (14)
H4E10.88700.32920.19210.054*0.8469 (14)
H4E20.92070.47570.20280.054*0.8469 (14)
H5E10.93770.25890.28800.038*0.8469 (14)
H5E20.95690.40680.29920.038*0.8469 (14)
H7E10.71060.54390.30120.061*0.8469 (14)
H7E20.59180.46680.34290.061*0.8469 (14)
H7E30.77580.46570.36420.061*0.8469 (14)
H9E10.70170.17090.22820.056*0.8469 (14)
H9E20.55520.14110.26580.056*0.8469 (14)
H9E30.52590.20210.19790.056*0.8469 (14)
H10M0.43760.47210.26690.070*0.8469 (14)
H10N0.36620.38400.22140.070*0.8469 (14)
H10O0.39540.32340.28930.070*0.8469 (14)
H2X0.30010.53310.14310.064*0.15
H4X0.75960.04120.37420.064*0.15
H3X0.84310.31970.29800.051*0.1531 (14)
H4X10.63510.46830.34760.051*0.1531 (14)
H4X20.79610.51300.32030.051*0.1531 (14)
H5X10.48710.54150.26240.051*0.1531 (14)
H5X20.63790.62480.24450.051*0.1531 (14)
H7X10.86420.49150.21690.064*0.1531 (14)
H7X20.81420.42070.16260.064*0.1531 (14)
H7X30.76900.57210.15930.064*0.1531 (14)
H9X10.46560.17970.28420.064*0.1531 (14)
H9X20.41550.32980.28180.064*0.1531 (14)
H9X30.39470.26670.22380.064*0.1531 (14)
H10P0.80240.21940.20640.064*0.1531 (14)
H10Q0.69380.11480.24090.064*0.1531 (14)
H10R0.62740.19810.17910.064*0.1531 (14)
H12F0.17200.34230.12220.047*0.8469 (14)
H13F0.06370.27710.08070.047*0.8469 (14)
H15F0.10900.35750.07600.045*0.8469 (14)
H16F0.33960.42260.02930.047*0.8469 (14)
H17G0.16920.31310.07370.048*0.8469 (14)
H17H0.24730.30610.01370.048*0.8469 (14)
H22F0.64800.16460.13190.048*0.8469 (14)
H23F0.42890.25260.08920.043*0.8469 (14)
H25F0.24720.11420.03840.043*0.8469 (14)
H26F0.47170.19160.08280.044*0.8469 (14)
H27G0.07350.09380.04230.036*0.8469 (14)
H27H0.16160.08790.01520.036*0.8469 (14)
H12Y0.64350.15260.13080.051*0.1531 (14)
H13Y0.40550.21670.08990.051*0.1531 (14)
H15Y0.57170.12980.06760.051*0.1531 (14)
H16Y0.80570.06970.02260.051*0.1531 (14)
H17K0.28990.18250.06220.051*0.1531 (14)
H17L0.21880.18420.00120.051*0.1531 (14)
H22Y0.19920.31740.11390.051*0.1531 (14)
H23Y0.02660.23590.07010.051*0.1531 (14)
H25Y0.19640.60740.01460.051*0.1531 (14)
H26Y0.01880.67670.06950.051*0.1531 (14)
H27K0.38190.40270.02950.051*0.1531 (14)
H27L0.29990.40340.02920.051*0.1531 (14)
H1G1.25480.43790.36890.054*0.8469 (14)
H3G0.76810.05980.14960.055*0.8469 (14)
H3G11.19820.03160.18430.036*0.8469 (14)
H4G11.01990.10250.25270.044*0.8469 (14)
H4G21.19570.13030.23530.044*0.8469 (14)
H5G11.28570.02300.32430.039*0.8469 (14)
H5G21.11170.02350.33730.039*0.8469 (14)
H7G11.41180.08830.24640.051*0.8469 (14)
H7G21.42710.24290.26890.051*0.8469 (14)
H7G31.47710.14420.31260.051*0.8469 (14)
H9G10.91780.13030.28970.051*0.8469 (14)
H9G20.95000.28440.29520.051*0.8469 (14)
H9G30.86580.20220.23590.051*0.8469 (14)
H10S1.25010.26980.19810.058*0.8469 (14)
H10T1.06650.28560.18030.058*0.8469 (14)
H10U1.15020.36870.23950.058*0.8469 (14)
H1Z0.88230.04550.10700.064*0.15
H3Z1.24410.43380.36780.064*0.15
H3Z11.20070.05520.32130.051*0.1531 (14)
H4Z11.42450.23430.29470.051*0.1531 (14)
H4Z21.44660.08160.29730.051*0.1531 (14)
H5Z11.35450.19140.19770.051*0.1531 (14)
H5Z21.41280.04490.19890.051*0.1531 (14)
H7Z11.23500.09500.24610.064*0.1531 (14)
H7Z21.05950.11540.21440.064*0.1531 (14)
H7Z31.20700.13690.17670.064*0.1531 (14)
H9Z11.00420.33620.27440.064*0.1531 (14)
H9Z21.14890.32850.23530.064*0.1531 (14)
H9Z30.97670.27800.20620.064*0.1531 (14)
H10V0.95040.00150.27990.064*0.1531 (14)
H10W0.89710.14220.30580.064*0.1531 (14)
H10$0.84870.08140.23870.064*0.1531 (14)
H12H1.33050.71540.39150.040*
H13H1.21710.90210.43550.036*
H15H0.88030.67310.48130.040*
H16H1.00100.49320.43420.042*
H17A0.84920.92930.47820.035*
H17B0.95170.91390.53730.035*
H22H0.67571.26820.60910.040*
H23H0.79001.08070.56310.039*
H25H1.10821.31340.50870.040*
H26H0.98941.49250.55710.042*
H27A1.04611.07220.45710.037*
H27B1.14961.05630.51600.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0503 (19)0.074 (2)0.0350 (16)0.0158 (17)0.0050 (13)0.0179 (16)
O2A0.0360 (16)0.0410 (17)0.0466 (17)0.0030 (13)0.0092 (13)0.0109 (13)
O3A0.0492 (18)0.034 (3)0.0410 (16)0.008 (2)0.0158 (14)0.0018 (16)
O4A0.0458 (18)0.0249 (17)0.037 (2)0.0067 (18)0.0123 (19)0.0024 (16)
C1A0.0274 (19)0.0291 (19)0.0311 (18)0.0006 (14)0.0021 (14)0.0016 (14)
C2A0.038 (2)0.032 (2)0.0288 (18)0.0030 (17)0.0020 (16)0.0027 (16)
C3A0.0313 (19)0.030 (2)0.0304 (18)0.0010 (15)0.0008 (15)0.0049 (15)
C4A0.046 (3)0.031 (2)0.045 (3)0.002 (2)0.002 (2)0.0076 (18)
C5A0.048 (2)0.034 (2)0.038 (2)0.0067 (17)0.0009 (17)0.0077 (16)
C6A0.035 (2)0.036 (2)0.032 (2)0.0009 (16)0.0091 (16)0.0010 (16)
C7A0.040 (2)0.052 (2)0.043 (2)0.0049 (18)0.0071 (17)0.0001 (18)
C8A0.0308 (19)0.027 (2)0.0287 (18)0.0005 (17)0.0021 (15)0.0006 (14)
C9A0.039 (2)0.053 (3)0.044 (2)0.0165 (19)0.0005 (18)0.0003 (19)
C10A0.063 (3)0.037 (2)0.041 (2)0.007 (2)0.000 (2)0.0133 (18)
N1B0.0322 (17)0.0396 (18)0.0345 (16)0.0007 (13)0.0009 (13)0.0066 (14)
C12B0.036 (2)0.037 (2)0.045 (2)0.0049 (17)0.0069 (18)0.0044 (18)
C13B0.035 (2)0.031 (2)0.049 (2)0.0053 (16)0.0043 (18)0.0118 (18)
C14B0.0281 (18)0.039 (2)0.0317 (18)0.0002 (15)0.0015 (14)0.0034 (15)
C15B0.0291 (18)0.032 (2)0.0362 (19)0.0016 (14)0.0017 (15)0.0014 (15)
C16B0.035 (2)0.036 (2)0.0354 (19)0.0024 (16)0.0031 (16)0.0042 (16)
C17B0.034 (2)0.036 (2)0.035 (2)0.0015 (16)0.0019 (16)0.0012 (16)
N2B0.0273 (16)0.0283 (16)0.0368 (17)0.0022 (12)0.0025 (13)0.0042 (13)
C22B0.038 (2)0.034 (2)0.037 (2)0.0012 (17)0.0058 (17)0.0009 (17)
C23B0.044 (2)0.033 (2)0.031 (2)0.0024 (17)0.0047 (17)0.0019 (16)
C24B0.034 (2)0.0244 (19)0.041 (2)0.0038 (15)0.0074 (17)0.0028 (16)
C25B0.030 (2)0.036 (2)0.040 (2)0.0029 (16)0.0058 (17)0.0075 (17)
C26B0.033 (2)0.040 (2)0.034 (2)0.0019 (17)0.0021 (16)0.0082 (17)
C27B0.037 (2)0.038 (2)0.055 (3)0.0001 (18)0.0170 (19)0.0067 (19)
O1C0.0318 (15)0.0335 (16)0.0423 (17)0.0045 (12)0.0064 (12)0.0095 (13)
O2C0.0322 (15)0.0461 (17)0.0335 (14)0.0005 (12)0.0041 (11)0.0094 (12)
O3C0.039 (3)0.0273 (14)0.0329 (16)0.0018 (14)0.0141 (18)0.0033 (11)
O4C0.047 (3)0.052 (3)0.0345 (16)0.0137 (19)0.0165 (14)0.0015 (17)
C1C0.0302 (19)0.0231 (18)0.0276 (18)0.0013 (14)0.0018 (14)0.0022 (14)
C2C0.0250 (18)0.0244 (19)0.0277 (18)0.0011 (14)0.0067 (14)0.0001 (14)
C3C0.032 (2)0.0254 (18)0.029 (2)0.0026 (14)0.0013 (15)0.0045 (15)
C4C0.033 (2)0.032 (3)0.030 (2)0.0089 (17)0.0011 (16)0.000 (2)
C5C0.0255 (18)0.0354 (19)0.0315 (18)0.0061 (14)0.0023 (14)0.0018 (14)
C6C0.0271 (18)0.0242 (18)0.0325 (18)0.0049 (14)0.0056 (15)0.0011 (15)
C7C0.051 (2)0.0238 (17)0.039 (2)0.0010 (15)0.0036 (17)0.0028 (14)
C8C0.031 (2)0.034 (2)0.0219 (18)0.0006 (15)0.0046 (16)0.0028 (15)
C9C0.035 (2)0.0273 (19)0.0325 (19)0.0088 (15)0.0041 (16)0.0014 (15)
C10C0.034 (2)0.051 (3)0.035 (2)0.0096 (18)0.0070 (16)0.0001 (18)
N1D0.0350 (15)0.0328 (15)0.0265 (13)0.0030 (11)0.0010 (11)0.0003 (11)
N2D0.0333 (15)0.0304 (15)0.0334 (14)0.0041 (11)0.0055 (11)0.0012 (11)
C12D0.0347 (18)0.0343 (18)0.0321 (16)0.0002 (14)0.0070 (14)0.0020 (13)
C13D0.0345 (17)0.0302 (17)0.0324 (16)0.0015 (13)0.0081 (13)0.0011 (13)
C14D0.0284 (16)0.0303 (17)0.0280 (15)0.0029 (12)0.0003 (12)0.0046 (12)
C15D0.0280 (16)0.0316 (17)0.0392 (18)0.0031 (13)0.0043 (14)0.0035 (14)
C16D0.0361 (18)0.0295 (17)0.0397 (18)0.0001 (14)0.0027 (15)0.0004 (14)
C17D0.0257 (16)0.0290 (16)0.0329 (16)0.0032 (12)0.0040 (12)0.0045 (13)
C22D0.0319 (17)0.0365 (18)0.0320 (16)0.0041 (14)0.0098 (13)0.0067 (13)
C23D0.0291 (16)0.0290 (16)0.0332 (16)0.0001 (12)0.0049 (13)0.0060 (13)
C24D0.0248 (15)0.0305 (16)0.0265 (14)0.0031 (12)0.0010 (12)0.0039 (12)
C25D0.0303 (17)0.0336 (18)0.044 (2)0.0002 (13)0.0124 (15)0.0038 (15)
C26D0.0310 (17)0.0297 (17)0.0431 (19)0.0006 (13)0.0071 (14)0.0049 (14)
C27D0.0308 (17)0.0284 (16)0.0359 (16)0.0030 (12)0.0111 (13)0.0053 (13)
O1E0.051 (3)0.037 (2)0.035 (2)0.0023 (16)0.0189 (19)0.0027 (14)
O2E0.0385 (18)0.0311 (17)0.034 (3)0.0034 (13)0.0117 (19)0.0064 (13)
O3E0.0419 (17)0.063 (2)0.0305 (14)0.0059 (15)0.0051 (12)0.0104 (14)
O4E0.052 (2)0.0408 (18)0.0417 (18)0.0010 (14)0.0137 (14)0.0027 (14)
C1E0.0263 (18)0.031 (2)0.0276 (18)0.0013 (16)0.0008 (14)0.0000 (16)
C2E0.028 (2)0.036 (2)0.0248 (18)0.0054 (16)0.0014 (15)0.0010 (16)
C3E0.038 (2)0.032 (2)0.032 (2)0.0087 (17)0.0016 (17)0.0015 (16)
C4E0.036 (2)0.067 (3)0.031 (2)0.016 (2)0.0048 (16)0.0034 (19)
C5E0.028 (2)0.032 (2)0.033 (2)0.0005 (15)0.0020 (15)0.0007 (16)
C6E0.0263 (18)0.031 (2)0.0297 (18)0.0001 (15)0.0032 (15)0.0044 (15)
C7E0.043 (2)0.038 (2)0.041 (2)0.0067 (16)0.000 (2)0.010 (2)
C8E0.035 (2)0.033 (2)0.033 (2)0.0068 (16)0.0004 (17)0.0029 (16)
C9E0.041 (2)0.034 (2)0.039 (2)0.0107 (17)0.0035 (17)0.0071 (17)
C10E0.031 (2)0.068 (3)0.042 (2)0.007 (2)0.0027 (17)0.014 (2)
N1F0.0371 (19)0.0297 (18)0.0368 (18)0.0011 (14)0.0016 (14)0.0008 (14)
N2F0.0363 (17)0.0293 (17)0.0371 (17)0.0001 (13)0.0019 (13)0.0033 (13)
C12F0.045 (3)0.040 (2)0.033 (2)0.0022 (19)0.0004 (18)0.0080 (17)
C13F0.039 (2)0.039 (2)0.041 (2)0.0001 (18)0.0061 (18)0.0056 (18)
C14F0.031 (2)0.0249 (19)0.042 (2)0.0033 (15)0.0053 (16)0.0059 (16)
C15F0.044 (2)0.036 (2)0.030 (2)0.0034 (17)0.0005 (17)0.0004 (16)
C16F0.036 (2)0.041 (2)0.037 (2)0.0042 (17)0.0011 (17)0.0018 (17)
C17F0.035 (2)0.030 (2)0.050 (2)0.0013 (16)0.0063 (18)0.0027 (18)
C22F0.039 (2)0.033 (2)0.043 (2)0.0019 (16)0.0085 (18)0.0040 (17)
C23F0.035 (2)0.0264 (19)0.043 (2)0.0019 (15)0.0016 (17)0.0005 (16)
C24F0.0282 (18)0.0286 (18)0.0277 (17)0.0036 (14)0.0039 (14)0.0055 (14)
C25F0.031 (2)0.0289 (19)0.045 (2)0.0065 (15)0.0032 (16)0.0053 (16)
C26F0.034 (2)0.0282 (19)0.047 (2)0.0047 (15)0.0053 (16)0.0091 (16)
C27F0.0264 (18)0.0304 (19)0.0331 (18)0.0017 (14)0.0003 (14)0.0081 (14)
O1G0.047 (2)0.0235 (17)0.038 (2)0.0042 (15)0.0181 (15)0.0015 (15)
O2G0.051 (2)0.049 (2)0.0242 (17)0.0135 (15)0.0114 (16)0.0066 (15)
O3G0.0317 (15)0.0350 (15)0.0420 (15)0.0081 (12)0.0052 (12)0.0083 (12)
O4G0.0456 (18)0.075 (3)0.0352 (16)0.0170 (17)0.0008 (13)0.0183 (16)
C1G0.028 (2)0.0202 (18)0.0292 (18)0.0038 (14)0.0011 (15)0.0032 (14)
C2G0.0258 (19)0.0265 (19)0.0282 (18)0.0010 (14)0.0043 (14)0.0024 (14)
C3G0.0299 (19)0.0279 (19)0.0293 (18)0.0019 (15)0.0029 (15)0.0020 (14)
C4G0.039 (2)0.0263 (18)0.043 (2)0.0005 (15)0.0094 (17)0.0025 (15)
C5G0.035 (2)0.0265 (19)0.0370 (19)0.0013 (15)0.0028 (16)0.0102 (15)
C6G0.0282 (19)0.027 (2)0.0271 (18)0.0038 (15)0.0008 (14)0.0088 (14)
C7G0.025 (2)0.040 (3)0.0367 (19)0.005 (2)0.0058 (15)0.0005 (16)
C8G0.0293 (19)0.038 (2)0.0282 (19)0.0066 (15)0.0021 (15)0.0014 (16)
C9G0.032 (2)0.034 (2)0.0341 (19)0.0066 (15)0.0017 (15)0.0011 (15)
C10G0.044 (2)0.037 (2)0.038 (2)0.0052 (17)0.0004 (17)0.0145 (17)
N1H0.0333 (15)0.0308 (15)0.0276 (13)0.0013 (11)0.0027 (11)0.0015 (11)
N2H0.0321 (15)0.0306 (15)0.0318 (14)0.0015 (11)0.0005 (11)0.0002 (11)
C12H0.0357 (18)0.0318 (18)0.0321 (16)0.0003 (13)0.0078 (13)0.0034 (13)
C13H0.0332 (17)0.0263 (16)0.0303 (15)0.0007 (13)0.0059 (13)0.0062 (12)
C14H0.0273 (16)0.0284 (16)0.0279 (15)0.0022 (12)0.0013 (12)0.0074 (12)
C15H0.0261 (16)0.0279 (17)0.0478 (19)0.0016 (12)0.0091 (14)0.0069 (14)
C16H0.0310 (17)0.0289 (17)0.0424 (18)0.0034 (13)0.0019 (14)0.0024 (13)
C17H0.0256 (16)0.0275 (16)0.0333 (16)0.0011 (12)0.0035 (12)0.0042 (13)
C22H0.0326 (17)0.0363 (18)0.0309 (16)0.0021 (14)0.0060 (13)0.0036 (13)
C23H0.0358 (18)0.0290 (17)0.0321 (16)0.0025 (13)0.0058 (14)0.0030 (13)
C24H0.0271 (16)0.0287 (16)0.0273 (14)0.0012 (12)0.0014 (12)0.0046 (12)
C25H0.0273 (16)0.0318 (17)0.0409 (18)0.0009 (13)0.0048 (13)0.0048 (13)
C26H0.0370 (18)0.0262 (17)0.0413 (18)0.0011 (13)0.0026 (14)0.0050 (13)
C27H0.0297 (16)0.0293 (16)0.0335 (16)0.0025 (12)0.0066 (13)0.0058 (13)
Geometric parameters (Å, º) top
O1A—C6A1.219 (5)O1E—C6E1.217 (5)
O1A—H4U0.84O2E—C6E1.323 (5)
O2A—C6A1.323 (5)O2E—H2E0.84
O2A—H2A0.84O3E—C8E1.212 (5)
O3A—C8A1.210 (5)O4E—C8E1.320 (5)
O4A—C8A1.330 (5)O4E—H4E0.84
O4A—H4A0.84C1E—C7E1.523 (5)
C1A—C6A1.515 (5)C1E—C6E1.526 (4)
C1A—C7A1.539 (5)C1E—C5E1.546 (6)
C1A—C5A1.549 (5)C1E—C2E1.586 (5)
C1A—C2A1.567 (5)C2E—C9E1.535 (5)
C2A—C10A1.530 (5)C2E—C10E1.535 (5)
C2A—C9A1.537 (5)C2E—C3E1.559 (5)
C2A—C3A1.568 (5)C3E—C8E1.509 (5)
C3A—C8A1.512 (4)C3E—C4E1.533 (5)
C3A—C4A1.541 (5)C3E—H3E1.00
C3A—H3A1.00C4E—C5E1.543 (5)
C4A—C5A1.537 (6)C4E—H4E10.99
C4A—H4A10.99C4E—H4E20.99
C4A—H4A20.99C5E—H5E10.99
C5A—H5A10.99C5E—H5E20.99
C5A—H5A20.99C7E—H7E10.98
C7A—H7A10.98C7E—H7E20.98
C7A—H7A20.98C7E—H7E30.98
C7A—H7A30.98C9E—H9E10.98
C9A—H9A10.98C9E—H9E20.98
C9A—H9A20.98C9E—H9E30.98
C9A—H9A30.98C10E—H10M0.98
C10A—H10A0.98C10E—H10N0.98
C10A—H10B0.98C10E—H10O0.98
C10A—H10C0.98O1X—C6X1.235 (9)
O1U—C6U1.218 (11)O2X—C6X1.323 (9)
O2U—C6U1.319 (11)O2X—H2X0.84
O2U—H2U0.84O3X—C8X1.227 (10)
O3U—C8U1.222 (9)O4X—C8X1.322 (11)
O4U—C8U1.330 (10)O4X—H4X0.84
O4U—H4U0.84C1X—C6X1.517 (9)
C1U—C6U1.493 (10)C1X—C7X1.537 (10)
C1U—C7U1.536 (10)C1X—C5X1.557 (10)
C1U—C2U1.559 (10)C1X—C2X1.558 (10)
C1U—C5U1.563 (10)C2X—C9X1.559 (10)
C2U—C9U1.553 (10)C2X—C10X1.566 (10)
C2U—C3U1.558 (10)C2X—C3X1.572 (11)
C2U—C10U1.562 (10)C3X—C8X1.520 (10)
C3U—C8U1.501 (9)C3X—C4X1.546 (10)
C3U—C4U1.546 (10)C3X—H3X1.00
C3U—H3U1.00C4X—C5X1.548 (10)
C4U—C5U1.546 (10)C4X—H4X10.99
C4U—H4U10.99C4X—H4X20.99
C4U—H4U20.99C5X—H5X10.99
C5U—H5U10.99C5X—H5X20.99
C5U—H5U20.99C7X—H7X10.98
C7U—H7U10.98C7X—H7X20.98
C7U—H7U20.98C7X—H7X30.98
C7U—H7U30.98C9X—H9X10.98
C9U—H9U10.98C9X—H9X20.98
C9U—H9U20.98C9X—H9X30.98
C9U—H9U30.98C10X—H10P0.98
C10U—H10D0.98C10X—H10Q0.98
C10U—H10E0.98C10X—H10R0.98
C10U—H10F0.98N1F—C12F1.328 (5)
N1B—C12B1.337 (5)N1F—C16F1.335 (5)
N1B—C16B1.341 (5)N2F—C22F1.329 (5)
C12B—C13B1.378 (6)N2F—C26F1.333 (5)
C12B—H12B0.95C12F—C13F1.381 (6)
C13B—C14B1.393 (6)C12F—H12F0.95
C13B—H13B0.95C13F—C14F1.387 (6)
C14B—C15B1.390 (6)C13F—H13F0.95
C14B—C17B1.504 (5)C14F—C15F1.383 (6)
C15B—C16B1.384 (5)C14F—C17F1.509 (6)
C15B—H15B0.95C15F—C16F1.391 (6)
C16B—H16B0.95C15F—H15F0.95
C17B—C27B1.509 (6)C16F—H16F0.95
C17B—H17E0.99C17F—C27F1.505 (5)
C17B—H17F0.99C17F—H17G0.99
N2B—C22B1.337 (5)C17F—H17H0.99
N2B—C26B1.349 (5)C22F—C23F1.383 (6)
C22B—C23B1.386 (6)C22F—H22F0.95
C22B—H22B0.95C23F—C24F1.386 (5)
C23B—C24B1.386 (6)C23F—H23F0.95
C23B—H23B0.95C24F—C25F1.385 (5)
C24B—C25B1.394 (6)C24F—C27F1.508 (5)
C24B—C27B1.511 (6)C25F—C26F1.383 (6)
C25B—C26B1.377 (6)C25F—H25F0.95
C25B—H25B0.95C26F—H26F0.95
C26B—H26B0.95C27F—H27G0.99
C27B—H27E0.99C27F—H27H0.99
C27B—H27F0.99N1Y—C12Y1.344 (10)
N1V—C16V1.341 (10)N1Y—C16Y1.346 (10)
N1V—C12V1.344 (10)C12Y—C13Y1.391 (10)
C12V—C13V1.392 (10)C12Y—H12Y0.95
C12V—H12V0.95C13Y—C14Y1.389 (10)
C13V—C14V1.383 (10)C13Y—H13Y0.95
C13V—H13V0.95C14Y—C15Y1.391 (10)
C14V—C15V1.391 (10)C14Y—C17Y1.499 (10)
C14V—C17V1.497 (10)C15Y—C16Y1.386 (10)
C15V—C16V1.392 (10)C15Y—H15Y0.95
C15V—H15V0.95C16Y—H16Y0.95
C16V—H16V0.95C17Y—C27Y1.508 (10)
C17V—C27V1.503 (10)C17Y—H17K0.99
C17V—H17I0.99C17Y—H17L0.99
C17V—H17J0.99N2Y—C22Y1.348 (10)
N2V—C22V1.345 (10)N2Y—C26Y1.348 (10)
N2V—C26V1.347 (10)C22Y—C23Y1.395 (10)
C22V—C23V1.396 (10)C22Y—H22Y0.95
C22V—H22V0.95C23Y—C24Y1.392 (10)
C23V—C24V1.390 (10)C23Y—H23Y0.95
C23V—H23V0.95C24Y—C25Y1.391 (10)
C24V—C25V1.391 (10)C24Y—C27Y1.506 (10)
C24V—C27V1.499 (10)C25Y—C26Y1.390 (10)
C25V—C26V1.380 (10)C25Y—H25Y0.95
C25V—H25V0.95C26Y—H26Y0.95
C26V—H26V0.95C27Y—H27K0.99
C27V—H27I0.99C27Y—H27L0.99
C27V—H27J0.99O1G—C6G1.327 (5)
O1C—C6C1.325 (5)O1G—H1G0.84
O1C—H1C0.84O2G—C6G1.212 (5)
O2C—C6C1.209 (5)O3G—C8G1.314 (5)
O3C—C8C1.314 (5)O3G—H3G0.84
O3C—H3C0.84O4G—C8G1.226 (5)
O4C—C8C1.218 (5)C1G—C6G1.522 (4)
C1C—C6C1.526 (4)C1G—C7G1.543 (5)
C1C—C7C1.538 (4)C1G—C5G1.548 (5)
C1C—C5C1.544 (5)C1G—C2G1.579 (5)
C1C—C2C1.568 (4)C2G—C10G1.534 (5)
C2C—C10C1.532 (5)C2G—C9G1.537 (4)
C2C—C9C1.534 (5)C2G—C3G1.557 (4)
C2C—C3C1.577 (5)C3G—C8G1.517 (5)
C3C—C8C1.511 (5)C3G—C4G1.535 (5)
C3C—C4C1.539 (5)C3G—H3G11.00
C3C—H3C11.00C4G—C5G1.549 (5)
C4C—C5C1.526 (6)C4G—H4G10.99
C4C—H4C10.99C4G—H4G20.99
C4C—H4C20.99C5G—H5G10.99
C5C—H5C10.99C5G—H5G20.99
C5C—H5C20.99C7G—H7G10.98
C7C—H7C10.98C7G—H7G20.98
C7C—H7C20.98C7G—H7G30.98
C7C—H7C30.98C9G—H9G10.98
C9C—H9C10.98C9G—H9G20.98
C9C—H9C20.98C9G—H9G30.98
C9C—H9C30.98C10G—H10S0.98
C10C—H10G0.98C10G—H10T0.98
C10C—H10H0.98C10G—H10U0.98
C10C—H10I0.98O1Z—C6Z1.323 (10)
O1W—C6W1.323 (11)O1Z—H1Z0.84
O1W—H1W0.84O2Z—C6Z1.217 (9)
O2W—C6W1.221 (11)O3Z—C8Z1.324 (10)
O3W—C8W1.318 (10)O3Z—H3Z0.84
O3W—H3W0.84O4Z—C8Z1.223 (10)
O4W—C8W1.208 (9)C1Z—C6Z1.505 (9)
C1W—C6W1.505 (10)C1Z—C7Z1.540 (10)
C1W—C7W1.543 (10)C1Z—C2Z1.563 (10)
C1W—C5W1.562 (10)C1Z—C5Z1.565 (10)
C1W—C2W1.566 (10)C2Z—C9Z1.554 (10)
C2W—C9W1.551 (10)C2Z—C10Z1.561 (10)
C2W—C3W1.562 (10)C2Z—C3Z1.565 (10)
C2W—C10W1.563 (10)C3Z—C8Z1.515 (10)
C3W—C8W1.507 (9)C3Z—C4Z1.539 (10)
C3W—C4W1.545 (10)C3Z—H3Z11.00
C3W—H3W11.00C4Z—C5Z1.550 (10)
C4W—C5W1.543 (10)C4Z—H4Z10.99
C4W—H4W10.99C4Z—H4Z20.99
C4W—H4W20.99C5Z—H5Z10.99
C5W—H5W10.99C5Z—H5Z20.99
C5W—H5W20.99C7Z—H7Z10.98
C7W—H7W10.98C7Z—H7Z20.98
C7W—H7W20.98C7Z—H7Z30.98
C7W—H7W30.98C9Z—H9Z10.98
C9W—H9W10.98C9Z—H9Z20.98
C9W—H9W20.98C9Z—H9Z30.98
C9W—H9W30.98C10Z—H10V0.98
C10W—H10J0.98C10Z—H10W0.98
C10W—H10K0.98C10Z—H10$0.98
C10W—H10L0.98N1H—C12H1.335 (4)
N1D—C16D1.336 (5)N1H—C16H1.338 (4)
N1D—C12D1.339 (4)N2H—C22H1.339 (4)
N2D—C22D1.330 (4)N2H—C26H1.340 (4)
N2D—C26D1.340 (4)C12H—C13H1.381 (4)
C12D—C13D1.379 (4)C12H—H12H0.95
C12D—H12D0.95C13H—C14H1.386 (4)
C13D—C14D1.388 (4)C13H—H13H0.95
C13D—H13D0.95C14H—C15H1.397 (4)
C14D—C15D1.397 (5)C14H—C17H1.503 (4)
C14D—C17D1.510 (4)C15H—C16H1.381 (5)
C15D—C16D1.386 (5)C15H—H15H0.95
C15D—H15D0.95C16H—H16H0.95
C16D—H16D0.95C17H—C27H1.526 (3)
C17D—C27D1.528 (4)C17H—H17A0.99
C17D—H17C0.99C17H—H17B0.99
C17D—H17D0.99C22H—C23H1.396 (5)
C22D—C23D1.396 (4)C22H—H22H0.95
C22D—H22D0.95C23H—C24H1.384 (4)
C23D—C24D1.387 (4)C23H—H23H0.95
C23D—H23D0.95C24H—C25H1.398 (5)
C24D—C25D1.385 (5)C24H—C27H1.510 (4)
C24D—C27D1.514 (4)C25H—C26H1.376 (5)
C25D—C26D1.373 (5)C25H—H25H0.95
C25D—H25D0.95C26H—H26H0.95
C26D—H26D0.95C27H—H27A0.99
C27D—H27C0.99C27H—H27B0.99
C27D—H27D0.99
C6A—C1A—C7A107.3 (3)C7E—C1E—C6E107.6 (4)
C6A—C1A—C5A115.8 (3)C7E—C1E—C5E109.5 (4)
C7A—C1A—C5A109.4 (3)C6E—C1E—C5E113.6 (3)
C6A—C1A—C2A110.0 (3)C7E—C1E—C2E111.8 (3)
C7A—C1A—C2A111.8 (3)C6E—C1E—C2E109.9 (3)
C5A—C1A—C2A102.6 (3)C5E—C1E—C2E104.5 (3)
C10A—C2A—C9A108.5 (4)C9E—C2E—C10E108.5 (3)
C10A—C2A—C1A114.1 (3)C9E—C2E—C3E110.4 (3)
C9A—C2A—C1A109.9 (3)C10E—C2E—C3E113.7 (3)
C10A—C2A—C3A112.7 (4)C9E—C2E—C1E111.2 (3)
C9A—C2A—C3A110.3 (3)C10E—C2E—C1E112.5 (3)
C1A—C2A—C3A101.2 (3)C3E—C2E—C1E100.5 (3)
C8A—C3A—C4A114.5 (4)C8E—C3E—C4E114.0 (3)
C8A—C3A—C2A111.0 (3)C8E—C3E—C2E111.5 (3)
C4A—C3A—C2A105.7 (3)C4E—C3E—C2E104.5 (3)
C8A—C3A—H3A108.5C8E—C3E—H3E108.9
C4A—C3A—H3A108.5C4E—C3E—H3E108.9
C2A—C3A—H3A108.5C2E—C3E—H3E108.9
C5A—C4A—C3A106.1 (4)C3E—C4E—C5E106.5 (3)
C5A—C4A—H4A1110.5C3E—C4E—H4E1110.4
C3A—C4A—H4A1110.5C5E—C4E—H4E1110.4
C5A—C4A—H4A2110.5C3E—C4E—H4E2110.4
C3A—C4A—H4A2110.5C5E—C4E—H4E2110.4
H4A1—C4A—H4A2108.7H4E1—C4E—H4E2108.6
C4A—C5A—C1A106.7 (3)C4E—C5E—C1E106.4 (3)
C4A—C5A—H5A1110.4C4E—C5E—H5E1110.5
C1A—C5A—H5A1110.4C1E—C5E—H5E1110.5
C4A—C5A—H5A2110.4C4E—C5E—H5E2110.5
C1A—C5A—H5A2110.4C1E—C5E—H5E2110.5
H5A1—C5A—H5A2108.6H5E1—C5E—H5E2108.6
O1A—C6A—O2A122.1 (4)O1E—C6E—O2E122.6 (4)
O1A—C6A—C1A123.1 (4)O1E—C6E—C1E122.6 (4)
O2A—C6A—C1A114.7 (3)O2E—C6E—C1E114.9 (3)
C1A—C7A—H7A1109.5C1E—C7E—H7E1109.5
C1A—C7A—H7A2109.5C1E—C7E—H7E2109.5
H7A1—C7A—H7A2109.5H7E1—C7E—H7E2109.5
C1A—C7A—H7A3109.5C1E—C7E—H7E3109.5
H7A1—C7A—H7A3109.5H7E1—C7E—H7E3109.5
H7A2—C7A—H7A3109.5H7E2—C7E—H7E3109.5
O3A—C8A—O4A123.4 (4)O3E—C8E—O4E122.5 (4)
O3A—C8A—C3A125.4 (4)O3E—C8E—C3E125.1 (4)
O4A—C8A—C3A111.2 (3)O4E—C8E—C3E112.3 (4)
C2A—C9A—H9A1109.5C2E—C9E—H9E1109.5
C2A—C9A—H9A2109.5C2E—C9E—H9E2109.5
H9A1—C9A—H9A2109.5H9E1—C9E—H9E2109.5
C2A—C9A—H9A3109.5C2E—C9E—H9E3109.5
H9A1—C9A—H9A3109.5H9E1—C9E—H9E3109.5
H9A2—C9A—H9A3109.5H9E2—C9E—H9E3109.5
C2A—C10A—H10A109.5C2E—C10E—H10M109.5
C2A—C10A—H10B109.5C2E—C10E—H10N109.5
H10A—C10A—H10B109.5H10M—C10E—H10N109.5
C2A—C10A—H10C109.5C2E—C10E—H10O109.5
H10A—C10A—H10C109.5H10M—C10E—H10O109.5
H10B—C10A—H10C109.5H10N—C10E—H10O109.5
C6U—O2U—H2U120.1C6X—O2X—H2X108.9
C8U—O4U—H4U118.4C8X—O4X—H4X110.7
C6U—C1U—C7U107 (2)C6X—C1X—C7X109.1 (13)
C6U—C1U—C2U111.9 (12)C6X—C1X—C5X113.4 (11)
C7U—C1U—C2U112.2 (14)C7X—C1X—C5X108.0 (11)
C6U—C1U—C5U113.7 (17)C6X—C1X—C2X110.7 (10)
C7U—C1U—C5U108.0 (13)C7X—C1X—C2X113.8 (11)
C2U—C1U—C5U104.0 (13)C5X—C1X—C2X101.8 (12)
C9U—C2U—C3U109.9 (16)C1X—C2X—C9X110.6 (15)
C9U—C2U—C1U113.8 (17)C1X—C2X—C10X113.9 (15)
C3U—C2U—C1U99.4 (11)C9X—C2X—C10X105.5 (12)
C9U—C2U—C10U107.5 (12)C1X—C2X—C3X102.6 (11)
C3U—C2U—C10U112.3 (16)C9X—C2X—C3X109.2 (18)
C1U—C2U—C10U113.8 (16)C10X—C2X—C3X115.1 (18)
C8U—C3U—C4U112.9 (12)C8X—C3X—C4X120 (2)
C8U—C3U—C2U111.4 (11)C8X—C3X—C2X108.7 (12)
C4U—C3U—C2U105.7 (13)C4X—C3X—C2X106.3 (14)
C8U—C3U—H3U108.9C8X—C3X—H3X106.9
C4U—C3U—H3U108.9C4X—C3X—H3X106.9
C2U—C3U—H3U108.9C2X—C3X—H3X106.9
C3U—C4U—C5U104.7 (9)C3X—C4X—C5X105.7 (11)
C3U—C4U—H4U1110.8C3X—C4X—H4X1110.6
C5U—C4U—H4U1110.8C5X—C4X—H4X1110.6
C3U—C4U—H4U2110.8C3X—C4X—H4X2110.6
C5U—C4U—H4U2110.8C5X—C4X—H4X2110.6
H4U1—C4U—H4U2108.9H4X1—C4X—H4X2108.7
C4U—C5U—C1U106.4 (10)C4X—C5X—C1X106.1 (10)
C4U—C5U—H5U1110.5C4X—C5X—H5X1110.5
C1U—C5U—H5U1110.5C1X—C5X—H5X1110.5
C4U—C5U—H5U2110.5C4X—C5X—H5X2110.5
C1U—C5U—H5U2110.5C1X—C5X—H5X2110.5
H5U1—C5U—H5U2108.6H5X1—C5X—H5X2108.7
O1U—C6U—O2U117 (2)O1X—C6X—O2X124.2 (13)
O1U—C6U—C1U125.7 (15)O1X—C6X—C1X121.1 (10)
O2U—C6U—C1U117.6 (12)O2X—C6X—C1X114.5 (9)
C1U—C7U—H7U1109.5C1X—C7X—H7X1109.5
C1U—C7U—H7U2109.5C1X—C7X—H7X2109.5
H7U1—C7U—H7U2109.5H7X1—C7X—H7X2109.5
C1U—C7U—H7U3109.5C1X—C7X—H7X3109.5
H7U1—C7U—H7U3109.5H7X1—C7X—H7X3109.5
H7U2—C7U—H7U3109.5H7X2—C7X—H7X3109.5
O3U—C8U—O4U119.7 (13)O3X—C8X—O4X123 (2)
O3U—C8U—C3U124.5 (11)O3X—C8X—C3X121.1 (13)
O4U—C8U—C3U115.7 (9)O4X—C8X—C3X115.4 (12)
C2U—C9U—H9U1109.5C2X—C9X—H9X1109.5
C2U—C9U—H9U2109.5C2X—C9X—H9X2109.5
H9U1—C9U—H9U2109.5H9X1—C9X—H9X2109.5
C2U—C9U—H9U3109.5C2X—C9X—H9X3109.5
H9U1—C9U—H9U3109.5H9X1—C9X—H9X3109.5
H9U2—C9U—H9U3109.5H9X2—C9X—H9X3109.5
C2U—C10U—H10D109.5C2X—C10X—H10P109.5
C2U—C10U—H10E109.5C2X—C10X—H10Q109.5
H10D—C10U—H10E109.5H10P—C10X—H10Q109.5
C2U—C10U—H10F109.5C2X—C10X—H10R109.5
H10D—C10U—H10F109.5H10P—C10X—H10R109.5
H10E—C10U—H10F109.5H10Q—C10X—H10R109.5
C12B—N1B—C16B116.9 (3)C12F—N1F—C16F116.9 (4)
N1B—C12B—C13B123.7 (4)C22F—N2F—C26F117.0 (3)
N1B—C12B—H12B118.1N1F—C12F—C13F124.3 (4)
C13B—C12B—H12B118.1N1F—C12F—H12F117.9
C12B—C13B—C14B119.7 (4)C13F—C12F—H12F117.9
C12B—C13B—H13B120.1C12F—C13F—C14F118.8 (4)
C14B—C13B—H13B120.1C12F—C13F—H13F120.6
C15B—C14B—C13B116.6 (4)C14F—C13F—H13F120.6
C15B—C14B—C17B119.5 (4)C15F—C14F—C13F117.5 (4)
C13B—C14B—C17B123.9 (4)C15F—C14F—C17F121.5 (4)
C16B—C15B—C14B120.2 (4)C13F—C14F—C17F121.0 (4)
C16B—C15B—H15B119.9C14F—C15F—C16F119.6 (4)
C14B—C15B—H15B119.9C14F—C15F—H15F120.2
N1B—C16B—C15B122.9 (4)C16F—C15F—H15F120.2
N1B—C16B—H16B118.6N1F—C16F—C15F122.9 (4)
C15B—C16B—H16B118.6N1F—C16F—H16F118.6
C14B—C17B—C27B115.1 (3)C15F—C16F—H16F118.6
C14B—C17B—H17E108.5C27F—C17F—C14F111.7 (3)
C27B—C17B—H17E108.5C27F—C17F—H17G109.3
C14B—C17B—H17F108.5C14F—C17F—H17G109.3
C27B—C17B—H17F108.5C27F—C17F—H17H109.3
H17E—C17B—H17F107.5C14F—C17F—H17H109.3
C22B—N2B—C26B116.5 (4)H17G—C17F—H17H107.9
N2B—C22B—C23B123.3 (4)N2F—C22F—C23F124.0 (4)
N2B—C22B—H22B118.3N2F—C22F—H22F118.0
C23B—C22B—H22B118.3C23F—C22F—H22F118.0
C22B—C23B—C24B119.7 (4)C22F—C23F—C24F119.3 (4)
C22B—C23B—H23B120.2C22F—C23F—H23F120.4
C24B—C23B—H23B120.2C24F—C23F—H23F120.4
C23B—C24B—C25B117.4 (4)C25F—C24F—C23F116.6 (3)
C23B—C24B—C27B122.5 (4)C25F—C24F—C27F119.8 (3)
C25B—C24B—C27B120.0 (4)C23F—C24F—C27F123.6 (3)
C26B—C25B—C24B119.1 (4)C26F—C25F—C24F120.5 (4)
C26B—C25B—H25B120.5C26F—C25F—H25F119.7
C24B—C25B—H25B120.5C24F—C25F—H25F119.7
N2B—C26B—C25B123.9 (4)N2F—C26F—C25F122.6 (4)
N2B—C26B—H26B118.1N2F—C26F—H26F118.7
C25B—C26B—H26B118.1C25F—C26F—H26F118.7
C17B—C27B—C24B112.4 (3)C17F—C27F—C24F115.3 (3)
C17B—C27B—H27E109.1C17F—C27F—H27G108.4
C24B—C27B—H27E109.1C24F—C27F—H27G108.4
C17B—C27B—H27F109.1C17F—C27F—H27H108.4
C24B—C27B—H27F109.1C24F—C27F—H27H108.4
H27E—C27B—H27F107.9H27G—C27F—H27H107.5
C16V—N1V—C12V119.0 (18)C12Y—N1Y—C16Y116.5 (19)
N1V—C12V—C13V123.0 (19)N1Y—C12Y—C13Y124 (2)
N1V—C12V—H12V118.5N1Y—C12Y—H12Y117.9
C13V—C12V—H12V118.5C13Y—C12Y—H12Y117.9
C14V—C13V—C12V119.7 (18)C14Y—C13Y—C12Y119 (2)
C14V—C13V—H13V120.2C14Y—C13Y—H13Y120.5
C12V—C13V—H13V120.2C12Y—C13Y—H13Y120.5
C13V—C14V—C15V115.7 (16)C13Y—C14Y—C15Y116.6 (17)
C13V—C14V—C17V123.4 (15)C13Y—C14Y—C17Y118.8 (16)
C15V—C14V—C17V120.8 (14)C15Y—C14Y—C17Y124.5 (16)
C14V—C15V—C16V123.0 (18)C16Y—C15Y—C14Y121.0 (18)
C14V—C15V—H15V118.5C16Y—C15Y—H15Y119.5
C16V—C15V—H15V118.5C14Y—C15Y—H15Y119.5
N1V—C16V—C15V119.4 (18)N1Y—C16Y—C15Y122.4 (19)
N1V—C16V—H16V120.3N1Y—C16Y—H16Y118.8
C15V—C16V—H16V120.3C15Y—C16Y—H16Y118.8
C14V—C17V—C27V116.9 (15)C14Y—C17Y—C27Y113.1 (16)
C14V—C17V—H17I108.1C14Y—C17Y—H17K109.0
C27V—C17V—H17I108.1C27Y—C17Y—H17K109.0
C14V—C17V—H17J108.1C14Y—C17Y—H17L109.0
C27V—C17V—H17J108.1C27Y—C17Y—H17L109.0
H17I—C17V—H17J107.3H17K—C17Y—H17L107.8
C22V—N2V—C26V119.9 (19)C22Y—N2Y—C26Y117.6 (19)
N2V—C22V—C23V123 (2)N2Y—C22Y—C23Y121 (2)
N2V—C22V—H22V118.3N2Y—C22Y—H22Y119.4
C23V—C22V—H22V118.3C23Y—C22Y—H22Y119.4
C24V—C23V—C22V117 (2)C24Y—C23Y—C22Y120 (2)
C24V—C23V—H23V121.3C24Y—C23Y—H23Y119.8
C22V—C23V—H23V121.3C22Y—C23Y—H23Y119.8
C23V—C24V—C25V118.0 (17)C25Y—C24Y—C23Y118.4 (18)
C23V—C24V—C27V122.6 (16)C25Y—C24Y—C27Y117.9 (15)
C25V—C24V—C27V119.4 (16)C23Y—C24Y—C27Y123.6 (17)
C26V—C25V—C24V122.3 (18)C26Y—C25Y—C24Y117.2 (18)
C26V—C25V—H25V118.8C26Y—C25Y—H25Y121.4
C24V—C25V—H25V118.8C24Y—C25Y—H25Y121.4
N2V—C26V—C25V118.9 (19)N2Y—C26Y—C25Y124.5 (19)
N2V—C26V—H26V120.6N2Y—C26Y—H26Y117.7
C25V—C26V—H26V120.6C25Y—C26Y—H26Y117.7
C24V—C27V—C17V112.5 (16)C24Y—C27Y—C17Y114.6 (15)
C24V—C27V—H27I109.1C24Y—C27Y—H27K108.6
C17V—C27V—H27I109.1C17Y—C27Y—H27K108.6
C24V—C27V—H27J109.1C24Y—C27Y—H27L108.6
C17V—C27V—H27J109.1C17Y—C27Y—H27L108.6
H27I—C27V—H27J107.8H27K—C27Y—H27L107.6
C6C—C1C—C7C108.8 (3)C6G—C1G—C7G110.9 (4)
C6C—C1C—C5C112.2 (3)C6G—C1G—C5G113.7 (3)
C7C—C1C—C5C109.8 (3)C7G—C1G—C5G108.9 (4)
C6C—C1C—C2C110.9 (3)C6G—C1G—C2G108.8 (3)
C7C—C1C—C2C112.3 (3)C7G—C1G—C2G112.0 (3)
C5C—C1C—C2C102.6 (3)C5G—C1G—C2G102.3 (3)
C10C—C2C—C9C108.0 (3)C10G—C2G—C9G108.4 (3)
C10C—C2C—C1C114.2 (3)C10G—C2G—C3G112.5 (3)
C9C—C2C—C1C110.5 (3)C9G—C2G—C3G109.6 (3)
C10C—C2C—C3C111.3 (3)C10G—C2G—C1G114.5 (3)
C9C—C2C—C3C112.1 (3)C9G—C2G—C1G109.9 (3)
C1C—C2C—C3C100.6 (3)C3G—C2G—C1G101.7 (3)
C8C—C3C—C4C117.4 (4)C8G—C3G—C4G116.8 (3)
C8C—C3C—C2C110.2 (3)C8G—C3G—C2G110.3 (3)
C4C—C3C—C2C107.0 (3)C4G—C3G—C2G105.5 (3)
C8C—C3C—H3C1107.3C8G—C3G—H3G1108.0
C4C—C3C—H3C1107.3C4G—C3G—H3G1108.0
C2C—C3C—H3C1107.3C2G—C3G—H3G1108.0
C5C—C4C—C3C106.1 (3)C3G—C4G—C5G106.4 (3)
C5C—C4C—H4C1110.5C3G—C4G—H4G1110.4
C3C—C4C—H4C1110.5C5G—C4G—H4G1110.4
C5C—C4C—H4C2110.5C3G—C4G—H4G2110.4
C3C—C4C—H4C2110.5C5G—C4G—H4G2110.4
H4C1—C4C—H4C2108.7H4G1—C4G—H4G2108.6
C4C—C5C—C1C105.0 (3)C1G—C5G—C4G106.5 (3)
C4C—C5C—H5C1110.7C1G—C5G—H5G1110.4
C1C—C5C—H5C1110.7C4G—C5G—H5G1110.4
C4C—C5C—H5C2110.7C1G—C5G—H5G2110.4
C1C—C5C—H5C2110.7C4G—C5G—H5G2110.4
H5C1—C5C—H5C2108.8H5G1—C5G—H5G2108.6
O2C—C6C—O1C122.5 (3)O2G—C6G—O1G122.4 (4)
O2C—C6C—C1C124.5 (3)O2G—C6G—C1G125.1 (4)
O1C—C6C—C1C113.0 (3)O1G—C6G—C1G112.4 (3)
C1C—C7C—H7C1109.5C1G—C7G—H7G1109.5
C1C—C7C—H7C2109.5C1G—C7G—H7G2109.5
H7C1—C7C—H7C2109.5H7G1—C7G—H7G2109.5
C1C—C7C—H7C3109.5C1G—C7G—H7G3109.5
H7C1—C7C—H7C3109.5H7G1—C7G—H7G3109.5
H7C2—C7C—H7C3109.5H7G2—C7G—H7G3109.5
O4C—C8C—O3C123.1 (4)O4G—C8G—O3G122.9 (4)
O4C—C8C—C3C121.9 (4)O4G—C8G—C3G121.2 (4)
O3C—C8C—C3C114.9 (3)O3G—C8G—C3G115.8 (4)
C2C—C9C—H9C1109.5C2G—C9G—H9G1109.5
C2C—C9C—H9C2109.5C2G—C9G—H9G2109.5
H9C1—C9C—H9C2109.5H9G1—C9G—H9G2109.5
C2C—C9C—H9C3109.5C2G—C9G—H9G3109.5
H9C1—C9C—H9C3109.5H9G1—C9G—H9G3109.5
H9C2—C9C—H9C3109.5H9G2—C9G—H9G3109.5
C2C—C10C—H10G109.5C2G—C10G—H10S109.5
C2C—C10C—H10H109.5C2G—C10G—H10T109.5
H10G—C10C—H10H109.5H10S—C10G—H10T109.5
C2C—C10C—H10I109.5C2G—C10G—H10U109.5
H10G—C10C—H10I109.5H10S—C10G—H10U109.5
H10H—C10C—H10I109.5H10T—C10G—H10U109.5
C6W—O1W—H1W106.3C6Z—O1Z—H1Z121.6
C8W—O3W—H3W111.2C8Z—O3Z—H3Z116.8
C6W—C1W—C7W104 (2)C6Z—C1Z—C7Z110.6 (13)
C6W—C1W—C5W122 (2)C6Z—C1Z—C2Z111.5 (10)
C7W—C1W—C5W107.6 (14)C7Z—C1Z—C2Z111.8 (11)
C6W—C1W—C2W109.6 (12)C6Z—C1Z—C5Z112.7 (11)
C7W—C1W—C2W109.7 (14)C7Z—C1Z—C5Z107.0 (11)
C5W—C1W—C2W103.7 (14)C2Z—C1Z—C5Z103.0 (12)
C9W—C2W—C3W109.4 (16)C9Z—C2Z—C10Z107.9 (12)
C9W—C2W—C10W107.1 (12)C9Z—C2Z—C1Z112.2 (14)
C3W—C2W—C10W113.3 (16)C10Z—C2Z—C1Z115.8 (14)
C9W—C2W—C1W107.3 (17)C9Z—C2Z—C3Z115.8 (17)
C3W—C2W—C1W103.2 (12)C10Z—C2Z—C3Z105.9 (17)
C10W—C2W—C1W116.2 (16)C1Z—C2Z—C3Z99.2 (11)
C8W—C3W—C4W118.1 (12)C8Z—C3Z—C4Z109 (2)
C8W—C3W—C2W109.8 (10)C8Z—C3Z—C2Z110.8 (12)
C4W—C3W—C2W104.4 (13)C4Z—C3Z—C2Z106.8 (16)
C8W—C3W—H3W1108.0C8Z—C3Z—H3Z1110.0
C4W—C3W—H3W1108.0C4Z—C3Z—H3Z1110.0
C2W—C3W—H3W1108.0C2Z—C3Z—H3Z1110.0
C5W—C4W—C3W108.2 (10)C3Z—C4Z—C5Z105.5 (11)
C5W—C4W—H4W1110.1C3Z—C4Z—H4Z1110.6
C3W—C4W—H4W1110.1C5Z—C4Z—H4Z1110.6
C5W—C4W—H4W2110.1C3Z—C4Z—H4Z2110.6
C3W—C4W—H4W2110.1C5Z—C4Z—H4Z2110.6
H4W1—C4W—H4W2108.4H4Z1—C4Z—H4Z2108.8
C4W—C5W—C1W105.7 (10)C4Z—C5Z—C1Z104.9 (10)
C4W—C5W—H5W1110.6C4Z—C5Z—H5Z1110.8
C1W—C5W—H5W1110.6C1Z—C5Z—H5Z1110.8
C4W—C5W—H5W2110.6C4Z—C5Z—H5Z2110.8
C1W—C5W—H5W2110.6C1Z—C5Z—H5Z2110.8
H5W1—C5W—H5W2108.7H5Z1—C5Z—H5Z2108.8
O2W—C6W—O1W120 (2)O2Z—C6Z—O1Z120.2 (14)
O2W—C6W—C1W123.9 (15)O2Z—C6Z—C1Z124.3 (11)
O1W—C6W—C1W116.3 (12)O1Z—C6Z—C1Z115.4 (9)
C1W—C7W—H7W1109.5C1Z—C7Z—H7Z1109.5
C1W—C7W—H7W2109.5C1Z—C7Z—H7Z2109.5
H7W1—C7W—H7W2109.5H7Z1—C7Z—H7Z2109.5
C1W—C7W—H7W3109.5C1Z—C7Z—H7Z3109.5
H7W1—C7W—H7W3109.5H7Z1—C7Z—H7Z3109.5
H7W2—C7W—H7W3109.5H7Z2—C7Z—H7Z3109.5
O4W—C8W—O3W118.6 (13)O4Z—C8Z—O3Z123 (2)
O4W—C8W—C3W124.9 (11)O4Z—C8Z—C3Z122.0 (14)
O3W—C8W—C3W116.4 (9)O3Z—C8Z—C3Z115.2 (12)
C2W—C9W—H9W1109.5C2Z—C9Z—H9Z1109.5
C2W—C9W—H9W2109.5C2Z—C9Z—H9Z2109.5
H9W1—C9W—H9W2109.5H9Z1—C9Z—H9Z2109.5
C2W—C9W—H9W3109.5C2Z—C9Z—H9Z3109.5
H9W1—C9W—H9W3109.5H9Z1—C9Z—H9Z3109.5
H9W2—C9W—H9W3109.5H9Z2—C9Z—H9Z3109.5
C2W—C10W—H10J109.5C2Z—C10Z—H10V109.5
C2W—C10W—H10K109.5C2Z—C10Z—H10W109.5
H10J—C10W—H10K109.5H10V—C10Z—H10W109.5
C2W—C10W—H10L109.5C2Z—C10Z—H10$109.5
H10J—C10W—H10L109.5H10V—C10Z—H10$109.5
H10K—C10W—H10L109.5H10W—C10Z—H10$109.5
C16D—N1D—C12D117.5 (3)C12H—N1H—C16H116.7 (3)
C22D—N2D—C26D116.9 (3)C22H—N2H—C26H117.7 (3)
N1D—C12D—C13D122.8 (3)N1H—C12H—C13H123.5 (3)
N1D—C12D—H12D118.6N1H—C12H—H12H118.3
C13D—C12D—H12D118.6C13H—C12H—H12H118.3
C12D—C13D—C14D120.4 (3)C12H—C13H—C14H120.1 (3)
C12D—C13D—H13D119.8C12H—C13H—H13H119.9
C14D—C13D—H13D119.8C14H—C13H—H13H119.9
C13D—C14D—C15D116.6 (3)C13H—C14H—C15H116.4 (3)
C13D—C14D—C17D124.1 (3)C13H—C14H—C17H124.0 (3)
C15D—C14D—C17D119.4 (3)C15H—C14H—C17H119.6 (3)
C16D—C15D—C14D119.5 (3)C16H—C15H—C14H119.7 (3)
C16D—C15D—H15D120.2C16H—C15H—H15H120.1
C14D—C15D—H15D120.2C14H—C15H—H15H120.1
N1D—C16D—C15D123.2 (3)N1H—C16H—C15H123.5 (3)
N1D—C16D—H16D118.4N1H—C16H—H16H118.2
C15D—C16D—H16D118.4C15H—C16H—H16H118.2
C14D—C17D—C27D115.4 (2)C14H—C17H—C27H115.4 (2)
C14D—C17D—H17C108.4C14H—C17H—H17A108.4
C27D—C17D—H17C108.4C27H—C17H—H17A108.4
C14D—C17D—H17D108.4C14H—C17H—H17B108.4
C27D—C17D—H17D108.4C27H—C17H—H17B108.4
H17C—C17D—H17D107.5H17A—C17H—H17B107.5
N2D—C22D—C23D123.3 (3)N2H—C22H—C23H122.3 (3)
N2D—C22D—H22D118.3N2H—C22H—H22H118.9
C23D—C22D—H22D118.3C23H—C22H—H22H118.9
C24D—C23D—C22D119.3 (3)C24H—C23H—C22H120.0 (3)
C24D—C23D—H23D120.3C24H—C23H—H23H120.0
C22D—C23D—H23D120.3C22H—C23H—H23H120.0
C25D—C24D—C23D116.9 (3)C23H—C24H—C25H117.0 (3)
C25D—C24D—C27D119.4 (3)C23H—C24H—C27H123.7 (3)
C23D—C24D—C27D123.7 (3)C25H—C24H—C27H119.3 (3)
C26D—C25D—C24D120.1 (3)C26H—C25H—C24H119.7 (3)
C26D—C25D—H25D119.9C26H—C25H—H25H120.2
C24D—C25D—H25D119.9C24H—C25H—H25H120.2
N2D—C26D—C25D123.4 (3)N2H—C26H—C25H123.3 (3)
N2D—C26D—H26D118.3N2H—C26H—H26H118.3
C25D—C26D—H26D118.3C25H—C26H—H26H118.3
C24D—C27D—C17D115.1 (2)C24H—C27H—C17H115.1 (2)
C24D—C27D—H27C108.5C24H—C27H—H27A108.5
C17D—C27D—H27C108.5C17H—C27H—H27A108.5
C24D—C27D—H27D108.5C24H—C27H—H27B108.5
C17D—C27D—H27D108.5C17H—C27H—H27B108.5
H27C—C27D—H27D107.5H27A—C27H—H27B107.5
C6A—C1A—C2A—C10A73.4 (4)C7E—C1E—C2E—C9E163.1 (4)
C7A—C1A—C2A—C10A45.7 (5)C6E—C1E—C2E—C9E43.6 (5)
C5A—C1A—C2A—C10A162.8 (4)C5E—C1E—C2E—C9E78.6 (4)
C6A—C1A—C2A—C9A48.7 (4)C7E—C1E—C2E—C10E41.2 (5)
C7A—C1A—C2A—C9A167.7 (3)C6E—C1E—C2E—C10E78.3 (4)
C5A—C1A—C2A—C9A75.1 (4)C5E—C1E—C2E—C10E159.5 (3)
C6A—C1A—C2A—C3A165.3 (3)C7E—C1E—C2E—C3E80.1 (4)
C7A—C1A—C2A—C3A75.7 (4)C6E—C1E—C2E—C3E160.4 (4)
C5A—C1A—C2A—C3A41.4 (4)C5E—C1E—C2E—C3E38.2 (4)
C10A—C2A—C3A—C8A76.8 (5)C9E—C2E—C3E—C8E47.3 (4)
C9A—C2A—C3A—C8A44.6 (5)C10E—C2E—C3E—C8E74.9 (5)
C1A—C2A—C3A—C8A160.9 (4)C1E—C2E—C3E—C8E164.7 (4)
C10A—C2A—C3A—C4A158.6 (4)C9E—C2E—C3E—C4E76.2 (4)
C9A—C2A—C3A—C4A80.0 (4)C10E—C2E—C3E—C4E161.6 (4)
C1A—C2A—C3A—C4A36.2 (4)C1E—C2E—C3E—C4E41.2 (4)
C8A—C3A—C4A—C5A139.3 (4)C8E—C3E—C4E—C5E151.1 (3)
C2A—C3A—C4A—C5A16.9 (5)C2E—C3E—C4E—C5E29.1 (4)
C3A—C4A—C5A—C1A9.7 (5)C3E—C4E—C5E—C1E4.5 (5)
C6A—C1A—C5A—C4A152.1 (4)C7E—C1E—C5E—C4E98.6 (4)
C7A—C1A—C5A—C4A86.6 (4)C6E—C1E—C5E—C4E141.1 (4)
C2A—C1A—C5A—C4A32.2 (4)C2E—C1E—C5E—C4E21.3 (4)
C7A—C1A—C6A—O1A57.3 (5)C7E—C1E—C6E—O1E31.6 (6)
C5A—C1A—C6A—O1A179.8 (4)C5E—C1E—C6E—O1E152.9 (5)
C2A—C1A—C6A—O1A64.5 (5)C2E—C1E—C6E—O1E90.4 (6)
C7A—C1A—C6A—O2A124.6 (4)C7E—C1E—C6E—O2E149.4 (5)
C5A—C1A—C6A—O2A2.1 (5)C5E—C1E—C6E—O2E28.0 (6)
C2A—C1A—C6A—O2A113.6 (4)C2E—C1E—C6E—O2E88.7 (5)
C4A—C3A—C8A—O3A19.5 (7)C4E—C3E—C8E—O3E17.0 (5)
C2A—C3A—C8A—O3A100.0 (7)C2E—C3E—C8E—O3E101.0 (4)
C4A—C3A—C8A—O4A163.1 (5)C4E—C3E—C8E—O4E162.4 (3)
C2A—C3A—C8A—O4A77.4 (5)C2E—C3E—C8E—O4E79.7 (4)
C6U—C1U—C2U—C9U48 (2)C6X—C1X—C2X—C9X45.6 (17)
C7U—C1U—C2U—C9U168 (2)C7X—C1X—C2X—C9X168.9 (15)
C5U—C1U—C2U—C9U75.0 (18)C5X—C1X—C2X—C9X75.2 (15)
C6U—C1U—C2U—C3U164.8 (17)C6X—C1X—C2X—C10X72.9 (16)
C7U—C1U—C2U—C3U75 (2)C7X—C1X—C2X—C10X50.4 (18)
C5U—C1U—C2U—C3U41.8 (17)C5X—C1X—C2X—C10X166.2 (15)
C6U—C1U—C2U—C10U76 (2)C6X—C1X—C2X—C3X162.0 (16)
C7U—C1U—C2U—C10U45 (2)C7X—C1X—C2X—C3X75 (2)
C5U—C1U—C2U—C10U161.4 (17)C5X—C1X—C2X—C3X41.2 (18)
C9U—C2U—C3U—C8U45.9 (19)C1X—C2X—C3X—C8X162.2 (15)
C1U—C2U—C3U—C8U165.6 (13)C9X—C2X—C3X—C8X45 (2)
C10U—C2U—C3U—C8U73.8 (17)C10X—C2X—C3X—C8X74 (2)
C9U—C2U—C3U—C4U77.1 (17)C1X—C2X—C3X—C4X31 (3)
C1U—C2U—C3U—C4U42.6 (18)C9X—C2X—C3X—C4X86 (2)
C10U—C2U—C3U—C4U163.3 (16)C10X—C2X—C3X—C4X155 (2)
C8U—C3U—C4U—C5U148.9 (16)C8X—C3X—C4X—C5X132 (2)
C2U—C3U—C4U—C5U27 (2)C2X—C3X—C4X—C5X8 (3)
C3U—C4U—C5U—C1U0 (2)C3X—C4X—C5X—C1X18 (3)
C6U—C1U—C5U—C4U148.6 (18)C6X—C1X—C5X—C4X156 (2)
C7U—C1U—C5U—C4U93 (2)C7X—C1X—C5X—C4X83 (2)
C2U—C1U—C5U—C4U27 (2)C2X—C1X—C5X—C4X37 (2)
C7U—C1U—C6U—O1U32 (3)C7X—C1X—C6X—O1X62.8 (17)
C2U—C1U—C6U—O1U92 (3)C5X—C1X—C6X—O1X176.7 (16)
C5U—C1U—C6U—O1U151 (3)C2X—C1X—C6X—O1X63.1 (18)
C7U—C1U—C6U—O2U147 (3)C7X—C1X—C6X—O2X121.8 (15)
C2U—C1U—C6U—O2U90 (3)C5X—C1X—C6X—O2X1.4 (18)
C5U—C1U—C6U—O2U28 (3)C2X—C1X—C6X—O2X112.3 (15)
C4U—C3U—C8U—O3U16 (2)C4X—C3X—C8X—O3X40 (3)
C2U—C3U—C8U—O3U102.9 (18)C2X—C3X—C8X—O3X83 (3)
C4U—C3U—C8U—O4U160.7 (17)C4X—C3X—C8X—O4X147 (3)
C2U—C3U—C8U—O4U80.5 (18)C2X—C3X—C8X—O4X90 (3)
C16B—N1B—C12B—C13B0.1 (6)C16F—N1F—C12F—C13F0.8 (7)
N1B—C12B—C13B—C14B0.1 (7)N1F—C12F—C13F—C14F0.1 (7)
C12B—C13B—C14B—C15B0.4 (6)C12F—C13F—C14F—C15F1.3 (6)
C12B—C13B—C14B—C17B177.3 (4)C12F—C13F—C14F—C17F179.0 (4)
C13B—C14B—C15B—C16B0.6 (6)C13F—C14F—C15F—C16F1.6 (6)
C17B—C14B—C15B—C16B177.2 (4)C17F—C14F—C15F—C16F178.6 (4)
C12B—N1B—C16B—C15B0.1 (6)C12F—N1F—C16F—C15F0.4 (6)
C14B—C15B—C16B—N1B0.5 (6)C14F—C15F—C16F—N1F0.8 (7)
C15B—C14B—C17B—C27B175.9 (4)C15F—C14F—C17F—C27F99.4 (5)
C13B—C14B—C17B—C27B1.7 (6)C13F—C14F—C17F—C27F80.3 (5)
C26B—N2B—C22B—C23B0.1 (6)C26F—N2F—C22F—C23F0.1 (6)
N2B—C22B—C23B—C24B1.8 (6)N2F—C22F—C23F—C24F0.8 (7)
C22B—C23B—C24B—C25B2.9 (6)C22F—C23F—C24F—C25F1.4 (6)
C22B—C23B—C24B—C27B177.2 (4)C22F—C23F—C24F—C27F178.4 (4)
C23B—C24B—C25B—C26B2.2 (6)C23F—C24F—C25F—C26F1.4 (6)
C27B—C24B—C25B—C26B177.8 (4)C27F—C24F—C25F—C26F178.4 (4)
C22B—N2B—C26B—C25B0.8 (6)C22F—N2F—C26F—C25F0.1 (6)
C24B—C25B—C26B—N2B0.4 (7)C24F—C25F—C26F—N2F0.8 (6)
C14B—C17B—C27B—C24B178.4 (4)C14F—C17F—C27F—C24F176.5 (3)
C23B—C24B—C27B—C17B102.9 (5)C25F—C24F—C27F—C17F177.4 (4)
C25B—C24B—C27B—C17B77.0 (5)C23F—C24F—C27F—C17F2.7 (5)
C16V—N1V—C12V—C13V1.7 (18)C16Y—N1Y—C12Y—C13Y1.8 (18)
N1V—C12V—C13V—C14V1.0 (16)N1Y—C12Y—C13Y—C14Y0.2 (17)
C12V—C13V—C14V—C15V0 (3)C12Y—C13Y—C14Y—C15Y1 (3)
C12V—C13V—C14V—C17V177.7 (16)C12Y—C13Y—C14Y—C17Y179.7 (15)
C13V—C14V—C15V—C16V3 (3)C13Y—C14Y—C15Y—C16Y1 (3)
C17V—C14V—C15V—C16V175 (2)C17Y—C14Y—C15Y—C16Y180 (2)
C12V—N1V—C16V—C15V5 (3)C12Y—N1Y—C16Y—C15Y2 (3)
C14V—C15V—C16V—N1V5 (3)C14Y—C15Y—C16Y—N1Y1 (4)
C13V—C14V—C17V—C27V7 (3)C13Y—C14Y—C17Y—C27Y78 (3)
C15V—C14V—C17V—C27V176 (2)C15Y—C14Y—C17Y—C27Y101 (3)
C26V—N2V—C22V—C23V0.2 (18)C26Y—N2Y—C22Y—C23Y0.0 (17)
N2V—C22V—C23V—C24V0.6 (16)N2Y—C22Y—C23Y—C24Y0.1 (16)
C22V—C23V—C24V—C25V1 (3)C22Y—C23Y—C24Y—C25Y4 (3)
C22V—C23V—C24V—C27V178.3 (16)C22Y—C23Y—C24Y—C27Y179.3 (16)
C23V—C24V—C25V—C26V4 (3)C23Y—C24Y—C25Y—C26Y8 (3)
C27V—C24V—C25V—C26V176 (2)C27Y—C24Y—C25Y—C26Y175 (2)
C22V—N2V—C26V—C25V3 (3)C22Y—N2Y—C26Y—C25Y4 (3)
C24V—C25V—C26V—N2V5 (3)C24Y—C25Y—C26Y—N2Y9 (3)
C23V—C24V—C27V—C17V78 (3)C25Y—C24Y—C27Y—C17Y179 (2)
C25V—C24V—C27V—C17V102 (2)C23Y—C24Y—C27Y—C17Y4 (3)
C14V—C17V—C27V—C24V177.3 (18)C14Y—C17Y—C27Y—C24Y176.3 (17)
C6C—C1C—C2C—C10C79.0 (4)C6G—C1G—C2G—C10G76.4 (4)
C7C—C1C—C2C—C10C43.1 (4)C7G—C1G—C2G—C10G46.5 (5)
C5C—C1C—C2C—C10C161.0 (3)C5G—C1G—C2G—C10G163.0 (3)
C6C—C1C—C2C—C9C43.1 (4)C6G—C1G—C2G—C9G45.8 (4)
C7C—C1C—C2C—C9C165.2 (3)C7G—C1G—C2G—C9G168.7 (4)
C5C—C1C—C2C—C9C76.9 (4)C5G—C1G—C2G—C9G74.8 (3)
C6C—C1C—C2C—C3C161.7 (3)C6G—C1G—C2G—C3G161.9 (3)
C7C—C1C—C2C—C3C76.2 (4)C7G—C1G—C2G—C3G75.1 (4)
C5C—C1C—C2C—C3C41.7 (3)C5G—C1G—C2G—C3G41.3 (3)
C10C—C2C—C3C—C8C81.1 (4)C10G—C2G—C3G—C8G73.0 (4)
C9C—C2C—C3C—C8C40.0 (5)C9G—C2G—C3G—C8G47.7 (4)
C1C—C2C—C3C—C8C157.4 (4)C1G—C2G—C3G—C8G164.0 (3)
C10C—C2C—C3C—C4C150.2 (3)C10G—C2G—C3G—C4G160.0 (3)
C9C—C2C—C3C—C4C88.6 (4)C9G—C2G—C3G—C4G79.3 (4)
C1C—C2C—C3C—C4C28.8 (4)C1G—C2G—C3G—C4G37.0 (3)
C8C—C3C—C4C—C5C129.2 (4)C8G—C3G—C4G—C5G141.1 (3)
C2C—C3C—C4C—C5C4.8 (4)C2G—C3G—C4G—C5G18.2 (4)
C3C—C4C—C5C—C1C21.9 (4)C6G—C1G—C5G—C4G148.1 (3)
C6C—C1C—C5C—C4C159.5 (3)C7G—C1G—C5G—C4G87.7 (4)
C7C—C1C—C5C—C4C79.3 (4)C2G—C1G—C5G—C4G30.9 (4)
C2C—C1C—C5C—C4C40.3 (4)C3G—C4G—C5G—C1G8.3 (4)
C7C—C1C—C6C—O2C131.9 (4)C7G—C1G—C6G—O2G139.6 (6)
C5C—C1C—C6C—O2C10.1 (5)C5G—C1G—C6G—O2G16.5 (7)
C2C—C1C—C6C—O2C104.0 (4)C2G—C1G—C6G—O2G96.8 (6)
C7C—C1C—C6C—O1C48.8 (4)C7G—C1G—C6G—O1G43.0 (6)
C5C—C1C—C6C—O1C170.6 (3)C5G—C1G—C6G—O1G166.2 (5)
C2C—C1C—C6C—O1C75.3 (4)C2G—C1G—C6G—O1G80.6 (5)
C4C—C3C—C8C—O4C150.8 (7)C4G—C3G—C8G—O4G170.2 (4)
C2C—C3C—C8C—O4C86.4 (7)C2G—C3G—C8G—O4G69.4 (5)
C4C—C3C—C8C—O3C31.2 (7)C4G—C3G—C8G—O3G12.4 (5)
C2C—C3C—C8C—O3C91.5 (6)C2G—C3G—C8G—O3G108.0 (4)
C6W—C1W—C2W—C9W54 (2)C6Z—C1Z—C2Z—C9Z42.9 (18)
C7W—C1W—C2W—C9W168 (2)C7Z—C1Z—C2Z—C9Z167.3 (15)
C5W—C1W—C2W—C9W77.2 (18)C5Z—C1Z—C2Z—C9Z78.2 (16)
C6W—C1W—C2W—C3W169.8 (18)C6Z—C1Z—C2Z—C10Z81.5 (16)
C7W—C1W—C2W—C3W76 (2)C7Z—C1Z—C2Z—C10Z42.8 (18)
C5W—C1W—C2W—C3W38.3 (19)C5Z—C1Z—C2Z—C10Z157.4 (15)
C6W—C1W—C2W—C10W66 (2)C6Z—C1Z—C2Z—C3Z165.8 (15)
C7W—C1W—C2W—C10W48 (2)C7Z—C1Z—C2Z—C3Z69.9 (18)
C5W—C1W—C2W—C10W163.0 (17)C5Z—C1Z—C2Z—C3Z44.7 (16)
C9W—C2W—C3W—C8W48.3 (18)C9Z—C2Z—C3Z—C8Z37 (2)
C10W—C2W—C3W—C8W71.2 (17)C10Z—C2Z—C3Z—C8Z82 (2)
C1W—C2W—C3W—C8W162.3 (14)C1Z—C2Z—C3Z—C8Z157.3 (15)
C9W—C2W—C3W—C4W79.3 (17)C9Z—C2Z—C3Z—C4Z82 (3)
C10W—C2W—C3W—C4W161.3 (16)C10Z—C2Z—C3Z—C4Z159 (3)
C1W—C2W—C3W—C4W34.8 (19)C1Z—C2Z—C3Z—C4Z38 (3)
C8W—C3W—C4W—C5W140.4 (17)C8Z—C3Z—C4Z—C5Z137 (3)
C2W—C3W—C4W—C5W18 (2)C2Z—C3Z—C4Z—C5Z17 (4)
C3W—C4W—C5W—C1W6 (2)C3Z—C4Z—C5Z—C1Z11 (4)
C6W—C1W—C5W—C4W151 (2)C6Z—C1Z—C5Z—C4Z156 (3)
C7W—C1W—C5W—C4W89 (2)C7Z—C1Z—C5Z—C4Z82 (3)
C2W—C1W—C5W—C4W27 (2)C2Z—C1Z—C5Z—C4Z36 (3)
C7W—C1W—C6W—O2W149 (3)C7Z—C1Z—C6Z—O2Z131.6 (17)
C5W—C1W—C6W—O2W28 (4)C2Z—C1Z—C6Z—O2Z103.4 (17)
C2W—C1W—C6W—O2W93 (4)C5Z—C1Z—C6Z—O2Z12 (2)
C7W—C1W—C6W—O1W31 (3)C7Z—C1Z—C6Z—O1Z52.0 (17)
C5W—C1W—C6W—O1W152 (4)C2Z—C1Z—C6Z—O1Z73.0 (17)
C2W—C1W—C6W—O1W87 (4)C5Z—C1Z—C6Z—O1Z171.7 (16)
C4W—C3W—C8W—O4W173.1 (19)C4Z—C3Z—C8Z—O4Z145 (3)
C2W—C3W—C8W—O4W67 (2)C2Z—C3Z—C8Z—O4Z97 (3)
C4W—C3W—C8W—O3W11 (2)C4Z—C3Z—C8Z—O3Z34 (3)
C2W—C3W—C8W—O3W109.0 (16)C2Z—C3Z—C8Z—O3Z83 (3)
C16D—N1D—C12D—C13D0.3 (5)C16H—N1H—C12H—C13H0.4 (5)
N1D—C12D—C13D—C14D1.5 (5)N1H—C12H—C13H—C14H0.9 (5)
C12D—C13D—C14D—C15D1.6 (5)C12H—C13H—C14H—C15H1.5 (5)
C12D—C13D—C14D—C17D178.1 (3)C12H—C13H—C14H—C17H177.9 (3)
C13D—C14D—C15D—C16D0.7 (5)C13H—C14H—C15H—C16H0.8 (5)
C17D—C14D—C15D—C16D179.0 (3)C17H—C14H—C15H—C16H178.6 (3)
C12D—N1D—C16D—C15D0.6 (5)C12H—N1H—C16H—C15H1.2 (5)
C14D—C15D—C16D—N1D0.4 (6)C14H—C15H—C16H—N1H0.6 (6)
C13D—C14D—C17D—C27D4.5 (4)C13H—C14H—C17H—C27H1.7 (4)
C15D—C14D—C17D—C27D175.2 (3)C15H—C14H—C17H—C27H177.6 (3)
C26D—N2D—C22D—C23D0.1 (5)C26H—N2H—C22H—C23H0.2 (5)
N2D—C22D—C23D—C24D0.7 (5)N2H—C22H—C23H—C24H0.5 (5)
C22D—C23D—C24D—C25D1.0 (5)C22H—C23H—C24H—C25H0.6 (5)
C22D—C23D—C24D—C27D178.4 (3)C22H—C23H—C24H—C27H178.5 (3)
C23D—C24D—C25D—C26D0.8 (5)C23H—C24H—C25H—C26H0.0 (5)
C27D—C24D—C25D—C26D178.6 (3)C27H—C24H—C25H—C26H179.1 (3)
C22D—N2D—C26D—C25D0.1 (5)C22H—N2H—C26H—C25H0.8 (5)
C24D—C25D—C26D—N2D0.3 (6)C24H—C25H—C26H—N2H0.7 (6)
C25D—C24D—C27D—C17D177.9 (3)C23H—C24H—C27H—C17H5.0 (4)
C23D—C24D—C27D—C17D1.4 (4)C25H—C24H—C27H—C17H174.1 (3)
C14D—C17D—C27D—C24D179.5 (3)C14H—C17H—C27H—C24H179.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A···N1B0.841.822.656 (4)173
O1C—H1C···N2B0.841.802.614 (4)163
O3C—H3C···N1D0.841.822.652 (6)174
O2E—H2E···N2D0.841.852.686 (6)175
O4E—H4E···N1F0.841.822.635 (5)162
O3G—H3G···N2F0.841.842.658 (4)166
O1G—H1G···N1H0.841.832.650 (7)167
O4A—H4A···N2Hi0.841.802.639 (6)176
C13F—H13F···O3Eii0.952.553.332 (6)140
C17B—H17E···O1Aii0.992.473.308 (5)142
C25B—H25B···O2Ciii0.952.503.272 (5)138
C27F—H27G···O4Giii0.992.303.182 (5)147
C16B—H16B···O3Eiv0.952.563.382 (5)145
C22D—H22D···O3Av0.952.563.429 (9)152
C22H—H22H···O1Ev0.952.523.386 (5)151
C26F—H26F···O2Cv0.952.483.279 (5)142
C12H—H12H···O4Cvi0.952.503.379 (10)153
O2U—H2U···N2Hi0.841.872.71 (4)180
O4U—H4U···N2V0.841.802.64 (2)180
O3W—H3W···N1V0.841.832.67 (2)180
O1W—H1W···N1D0.841.902.74 (4)180
O4X—H4X···N2D0.841.702.54 (4)180
O2X—H2X···N2Y0.841.802.64 (2)180
O1Z—H1Z···N1Y0.841.722.56 (2)180
O3Z—H3Z···N1H0.841.832.67 (4)180
O2U—H2U···N2Hi0.841.872.71 (4)180
Symmetry codes: (i) x+3, y+3, z+2; (ii) x1, y, z; (iii) x+1, y, z; (iv) x+1, y+1, z+1; (v) x1, y1, z1; (vi) x2, y2, z1.
(IV) (1R,3S)-Camphoric acid–1,4-diazabicyclo[2.2.2]octane–water (1/1/1) top
Crystal data top
C6H13N2·C10H15O4·H2OF(000) = 720
Mr = 330.42Dx = 1.272 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1768 reflections
a = 7.0310 (3) Åθ = 2.6–25.0°
b = 11.2520 (5) ŵ = 0.09 mm1
c = 21.8177 (12) ÅT = 150 K
V = 1726.06 (14) Å3Plate, colourless
Z = 40.38 × 0.32 × 0.11 mm
Data collection top
Kappa-CCD
diffractometer
1423 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.058
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
φ scans, and ω scans with κ offsetsh = 08
7008 measured reflectionsk = 013
1768 independent reflectionsl = 025
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0751P)2 + 0.4401P]
where P = (Fo2 + 2Fc2)/3
1768 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.31 e Å3
154 restraintsΔρmin = 0.17 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.3946 (4)0.2585 (2)0.11569 (12)0.0464 (7)
O20.0905 (3)0.3091 (3)0.11619 (11)0.0496 (7)
O30.4852 (6)0.2501 (3)0.38038 (16)0.0531 (9)0.828 (5)
O40.1745 (5)0.2704 (3)0.39484 (15)0.0475 (9)0.828 (5)
C10.2847 (4)0.3833 (3)0.19853 (13)0.0269 (7)
C20.1960 (4)0.3174 (3)0.25545 (13)0.0283 (7)
C30.3033 (5)0.3765 (3)0.31058 (13)0.0308 (7)
C40.4957 (5)0.4176 (3)0.28620 (15)0.0415 (9)
C50.4951 (5)0.3941 (3)0.21707 (15)0.0381 (8)
C60.2535 (5)0.3130 (3)0.13903 (15)0.0333 (7)
C70.2012 (6)0.5084 (3)0.19023 (17)0.0474 (10)
C80.3332 (6)0.2938 (4)0.36514 (19)0.0358 (10)0.828 (5)
C90.0188 (5)0.3317 (4)0.26240 (17)0.0464 (10)
C100.2418 (5)0.1839 (3)0.25171 (15)0.0397 (9)
N10.2817 (5)0.0891 (2)0.02925 (13)0.0485 (12)0.828 (5)
N20.3063 (4)0.0882 (2)0.04047 (12)0.0340 (9)0.828 (5)
C110.4843 (5)0.0666 (3)0.01434 (18)0.0528 (13)0.828 (5)
C120.1761 (6)0.1121 (4)0.02843 (15)0.0505 (13)0.828 (5)
C130.2009 (6)0.0173 (3)0.05952 (16)0.0520 (14)0.828 (5)
C210.4991 (5)0.0488 (3)0.02227 (19)0.0534 (13)0.828 (5)
C220.2074 (6)0.0090 (3)0.07306 (17)0.0437 (13)0.828 (5)
C230.1974 (6)0.1221 (3)0.01484 (15)0.0477 (12)0.828 (5)
N110.212 (2)0.0840 (13)0.0311 (7)0.069 (4)*0.172 (5)
N120.209 (2)0.0933 (13)0.0393 (7)0.069 (4)*0.172 (5)
C310.285 (3)0.114 (2)0.0306 (9)0.069 (4)*0.172 (5)
C320.013 (2)0.0415 (18)0.0260 (10)0.069 (4)*0.172 (5)
C330.331 (3)0.0108 (19)0.0582 (9)0.069 (4)*0.172 (5)
C410.276 (4)0.010 (2)0.0754 (10)0.069 (4)*0.172 (5)
C420.016 (2)0.0681 (18)0.0154 (10)0.069 (4)*0.172 (5)
C430.340 (3)0.114 (2)0.0127 (9)0.069 (4)*0.172 (5)
O50.7727 (4)0.1588 (2)0.12549 (15)0.0622 (9)
O130.098 (2)0.3170 (15)0.3928 (7)0.040*0.172 (5)
O140.383 (2)0.2359 (14)0.3803 (8)0.040*0.172 (5)
C580.247 (2)0.309 (2)0.3669 (8)0.040*0.172 (5)
H30.22960.44760.32450.037*
H40.19580.21710.42100.071*0.828 (5)
H4A0.59990.37280.30620.050*
H4B0.51420.50330.29450.050*
H5A0.56430.31970.20760.046*
H5B0.55650.46050.19480.046*
H7A0.27330.55100.15870.071*
H7B0.20930.55190.22910.071*
H7C0.06780.50220.17760.071*
H9A0.08260.29930.22610.070*
H9B0.05010.41610.26660.070*
H9C0.06170.28860.29890.070*
H10A0.19370.14380.28850.060*
H10B0.37990.17290.24900.060*
H10C0.18120.14980.21530.060*
H20.31640.15370.06630.041*0.828 (5)
H11A0.55940.05990.05260.063*0.828 (5)
H11B0.53600.13340.01000.063*0.828 (5)
H12A0.22120.18710.04710.061*0.828 (5)
H12B0.03870.12050.01950.061*0.828 (5)
H13A0.07010.00010.07370.062*0.828 (5)
H13B0.27880.03810.09580.062*0.828 (5)
H21A0.57800.03580.05930.064*0.828 (5)
H21B0.56080.11090.00300.064*0.828 (5)
H22A0.08350.01960.08880.052*0.828 (5)
H22B0.28500.03600.10830.052*0.828 (5)
H23A0.25510.19300.03420.057*0.828 (5)
H23B0.06450.14140.00360.057*0.828 (5)
H120.20500.16040.06410.083*0.172 (5)
H31A0.41860.14110.02690.083*0.172 (5)
H31B0.20960.18090.04740.083*0.172 (5)
H32A0.06820.10420.00800.083*0.172 (5)
H32B0.03720.02070.06690.083*0.172 (5)
H33A0.27590.03790.09750.083*0.172 (5)
H33B0.46110.01960.06620.083*0.172 (5)
H41A0.18740.02720.10940.083*0.172 (5)
H41B0.40380.00650.09280.083*0.172 (5)
H42A0.03050.13780.00800.083*0.172 (5)
H42B0.07220.05530.05030.083*0.172 (5)
H43A0.47130.12290.00280.083*0.172 (5)
H43B0.30430.18890.03380.083*0.172 (5)
H510.66620.20320.12490.080*
H520.86600.21350.12550.080*
H140.34740.18800.40740.060*0.172 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0421 (14)0.0547 (16)0.0423 (14)0.0034 (13)0.0005 (12)0.0213 (13)
O20.0422 (14)0.0657 (18)0.0408 (14)0.0020 (14)0.0115 (12)0.0076 (14)
O30.049 (2)0.061 (2)0.049 (2)0.006 (2)0.0076 (18)0.0141 (17)
O40.0484 (19)0.050 (2)0.0441 (18)0.0012 (16)0.0120 (16)0.0184 (16)
C10.0276 (16)0.0262 (15)0.0268 (15)0.0002 (13)0.0047 (13)0.0010 (13)
C20.0302 (16)0.0257 (15)0.0290 (16)0.0006 (14)0.0043 (14)0.0010 (14)
C30.0391 (17)0.0265 (15)0.0270 (16)0.0021 (15)0.0057 (15)0.0020 (13)
C40.038 (2)0.055 (2)0.0312 (18)0.0118 (18)0.0041 (16)0.0039 (17)
C50.0333 (19)0.049 (2)0.0322 (18)0.0134 (17)0.0026 (15)0.0060 (17)
C60.0389 (18)0.0310 (16)0.0301 (16)0.0049 (15)0.0013 (15)0.0020 (14)
C70.069 (3)0.0340 (18)0.039 (2)0.005 (2)0.002 (2)0.0043 (16)
C80.045 (3)0.029 (2)0.033 (2)0.008 (2)0.010 (2)0.0040 (19)
C90.0304 (18)0.060 (2)0.049 (2)0.0017 (18)0.0077 (16)0.0029 (19)
C100.056 (2)0.0251 (16)0.0381 (18)0.0068 (15)0.0001 (18)0.0002 (15)
N10.095 (3)0.0265 (18)0.0245 (18)0.013 (2)0.002 (2)0.0022 (15)
N20.050 (2)0.0267 (17)0.0253 (17)0.0009 (17)0.0017 (17)0.0048 (14)
C110.071 (3)0.044 (3)0.044 (3)0.004 (2)0.012 (2)0.004 (2)
C120.075 (3)0.037 (2)0.039 (2)0.015 (3)0.004 (3)0.003 (2)
C130.086 (4)0.042 (3)0.027 (2)0.010 (3)0.015 (2)0.0007 (19)
C210.050 (3)0.051 (3)0.059 (3)0.001 (2)0.002 (2)0.017 (2)
C220.066 (4)0.038 (2)0.027 (2)0.001 (3)0.001 (2)0.0021 (18)
C230.074 (3)0.039 (2)0.030 (2)0.008 (2)0.016 (2)0.0041 (19)
O50.0615 (18)0.0398 (15)0.085 (2)0.0043 (14)0.0098 (16)0.0021 (14)
Geometric parameters (Å, º) top
O1—C61.273 (4)C12—C221.530 (4)
O2—C61.251 (4)C12—H12A0.99
O3—C81.222 (5)C12—H12B0.99
O4—C81.317 (5)C13—C231.530 (4)
O4—H40.84C13—H13A0.99
C1—C61.535 (4)C13—H13B0.99
C1—C71.536 (4)C21—H21A0.99
C1—C51.538 (4)C21—H21B0.99
C1—C21.575 (4)C22—H22A0.99
C2—C91.526 (5)C22—H22B0.99
C2—C101.539 (4)C23—H23A0.99
C2—C31.567 (4)C23—H23B0.99
C3—C81.526 (5)N11—C331.481 (3)
C3—C41.526 (5)N11—C321.481 (3)
C3—H31.00N11—C311.481 (3)
C4—C51.531 (4)N12—C421.481 (3)
C4—H4A0.99N12—C431.481 (3)
C4—H4B0.99N12—C411.481 (3)
C5—H5A0.99N12—H120.93
C5—H5B0.99C31—C411.529 (4)
C7—H7A0.98C31—H31A0.99
C7—H7B0.98C31—H31B0.99
C7—H7C0.98C32—C421.529 (4)
C9—H9A0.98C32—H32A0.99
C9—H9B0.98C32—H32B0.99
C9—H9C0.98C33—C431.529 (4)
C10—H10A0.98C33—H33A0.99
C10—H10B0.98C33—H33B0.99
C10—H10C0.98C41—H41A0.99
N1—C131.480 (3)C41—H41B0.99
N1—C111.483 (3)C42—H42A0.99
N1—C121.484 (3)C42—H42B0.99
N2—C221.479 (3)C43—H43A0.99
N2—C231.479 (3)C43—H43B0.99
N2—C211.481 (3)O5—H510.90
N2—H20.93O5—H520.90
C11—C211.528 (4)O13—C581.194 (10)
C11—H11A0.99O14—C581.300 (10)
C11—H11B0.99O14—H140.84
C8—O3—H1472.3N2—C21—C11109.4 (2)
C8—O4—H4109.0N2—C21—H21A109.8
C6—C1—C7108.5 (3)C11—C21—H21A109.8
C6—C1—C5113.6 (3)N2—C21—H21B109.8
C7—C1—C5109.0 (3)C11—C21—H21B109.8
C6—C1—C2111.6 (2)H21A—C21—H21B108.2
C7—C1—C2111.9 (3)N2—C22—C12108.8 (2)
C5—C1—C2102.2 (2)N2—C22—H22A109.9
C9—C2—C10108.4 (3)C12—C22—H22A109.9
C9—C2—C3110.8 (3)N2—C22—H22B109.9
C10—C2—C3110.7 (3)C12—C22—H22B109.9
C9—C2—C1114.9 (3)H22A—C22—H22B108.3
C10—C2—C1109.5 (2)N2—C23—C13108.2 (2)
C3—C2—C1102.4 (2)N2—C23—H23A110.1
C8—C3—C4109.5 (3)C13—C23—H23A110.1
C8—C3—C2114.0 (3)N2—C23—H23B110.1
C4—C3—C2106.7 (2)C13—C23—H23B110.1
C8—C3—H3108.8H23A—C23—H23B108.4
C4—C3—H3108.8C33—N11—C32109.4 (3)
C2—C3—H3108.8C33—N11—C31109.3 (3)
C3—C4—C5106.7 (3)C32—N11—C31109.4 (3)
C3—C4—H4A110.4C42—N12—C43109.4 (3)
C5—C4—H4A110.4C42—N12—C41109.4 (3)
C3—C4—H4B110.4C43—N12—C41109.4 (3)
C5—C4—H4B110.4C42—N12—H12109.5
H4A—C4—H4B108.6C43—N12—H12109.5
C4—C5—C1106.0 (3)C41—N12—H12109.5
C4—C5—H5A110.5N11—C31—C41113.0 (13)
C1—C5—H5A110.5N11—C31—H31A109.0
C4—C5—H5B110.5C41—C31—H31A109.0
C1—C5—H5B110.5N11—C31—H31B109.0
H5A—C5—H5B108.7C41—C31—H31B109.0
O2—C6—O1122.5 (3)H31A—C31—H31B107.8
O2—C6—C1119.1 (3)N11—C32—C42107.2 (12)
O1—C6—C1118.4 (3)N11—C32—H32A110.3
O3—C8—O4121.8 (4)C42—C32—H32A110.3
O3—C8—C3125.3 (3)N11—C32—H32B110.3
O4—C8—C3112.9 (3)C42—C32—H32B110.3
O3—C8—H1457.2H32A—C32—H32B108.5
O4—C8—H1466.3N11—C33—C43108.1 (12)
C3—C8—H14165.3N11—C33—H33A110.1
C13—N1—C11109.17 (19)C43—C33—H33A110.1
C13—N1—C12109.12 (19)N11—C33—H33B110.1
C11—N1—C12108.94 (19)C43—C33—H33B110.1
C22—N2—C23109.82 (19)H33A—C33—H33B108.4
C22—N2—C21109.75 (19)N12—C41—C31105.9 (13)
C23—N2—C21109.43 (19)N12—C41—H41A110.6
C22—N2—H2109.3C31—C41—H41A110.6
C23—N2—H2109.3N12—C41—H41B110.6
C21—N2—H2109.3C31—C41—H41B110.6
N1—C11—C21109.0 (2)H41A—C41—H41B108.7
N1—C11—H11A109.9N12—C42—C32111.8 (12)
C21—C11—H11A109.9N12—C42—H42A109.3
N1—C11—H11B109.9C32—C42—H42A109.3
C21—C11—H11B109.9N12—C42—H42B109.3
H11A—C11—H11B108.3C32—C42—H42B109.3
N1—C12—C22109.6 (2)H42A—C42—H42B107.9
N1—C12—H12A109.8N12—C43—C33110.6 (12)
C22—C12—H12A109.8N12—C43—H43A109.5
N1—C12—H12B109.8C33—C43—H43A109.5
C22—C12—H12B109.8N12—C43—H43B109.5
H12A—C12—H12B108.2C33—C43—H43B109.5
N1—C13—C23110.2 (2)H43A—C43—H43B108.1
N1—C13—H13A109.6H51—O5—H52103.1
C23—C13—H13A109.6C58—O13—H474.2
N1—C13—H13B109.6C58—O14—H14110.3
C23—C13—H13B109.6O13—C58—O14126.0 (14)
H13A—C13—H13B108.1
C6—C1—C2—C979.2 (3)C13—N1—C11—C2153.3 (4)
C7—C1—C2—C942.6 (4)C12—N1—C11—C2165.8 (4)
C5—C1—C2—C9159.1 (3)C13—N1—C12—C2264.5 (3)
C6—C1—C2—C1043.0 (3)C11—N1—C12—C2254.6 (3)
C7—C1—C2—C10164.9 (3)C11—N1—C13—C2365.4 (4)
C5—C1—C2—C1078.7 (3)C12—N1—C13—C2353.5 (4)
C6—C1—C2—C3160.6 (3)C22—N2—C21—C1154.0 (4)
C7—C1—C2—C377.6 (3)C23—N2—C21—C1166.6 (4)
C5—C1—C2—C338.8 (3)N1—C11—C21—N210.2 (4)
C9—C2—C3—C888.5 (4)C23—N2—C22—C1255.2 (3)
C10—C2—C3—C831.7 (4)C21—N2—C22—C1265.1 (3)
C1—C2—C3—C8148.4 (3)N1—C12—C22—N29.1 (4)
C9—C2—C3—C4150.4 (3)C22—N2—C23—C1366.1 (4)
C10—C2—C3—C489.4 (3)C21—N2—C23—C1354.4 (4)
C1—C2—C3—C427.3 (3)N1—C13—C23—N29.7 (4)
C8—C3—C4—C5128.9 (3)C33—N11—C31—C4162.1 (18)
C2—C3—C4—C55.1 (4)C32—N11—C31—C4157.7 (18)
C3—C4—C5—C120.1 (4)C33—N11—C32—C4260.0 (17)
C6—C1—C5—C4157.1 (3)C31—N11—C32—C4259.7 (17)
C7—C1—C5—C481.7 (3)C32—N11—C33—C4366.1 (18)
C2—C1—C5—C436.8 (3)C31—N11—C33—C4353.6 (18)
C7—C1—C6—O251.2 (4)C42—N12—C41—C3162.0 (17)
C5—C1—C6—O2172.6 (3)C43—N12—C41—C3157.8 (17)
C2—C1—C6—O272.5 (4)N11—C31—C41—N124 (2)
C7—C1—C6—O1130.5 (3)C43—N12—C42—C3259.7 (18)
C5—C1—C6—O19.1 (4)C41—N12—C42—C3260.1 (17)
C2—C1—C6—O1105.8 (3)N11—C32—C42—N123 (2)
C4—C3—C8—O312.0 (6)C42—N12—C43—C3353.5 (18)
C2—C3—C8—O3107.5 (5)C41—N12—C43—C3366.3 (18)
C4—C3—C8—O4169.4 (3)N11—C33—C43—N127 (2)
C2—C3—C8—O471.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.931.692.598 (4)165
O4—H4···N1i0.841.812.646 (4)172
O5—H51···O10.902.022.894 (4)164
O5—H52···O2ii0.901.922.810 (4)169
C23—H23A···O5iii0.992.603.491 (4)150
O14—H14···N11i0.841.832.67 (2)176
N12—H12···O20.932.183.066 (13)160
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x+1, y, z; (iii) x1/2, y+1/2, z.
(V) (1R,3S)-Camphoric acid–hexamethylenetetramine (2/1) top
Crystal data top
2(C10H16O4)·C6H12N4F(000) = 584
Mr = 540.65Dx = 1.256 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 1866 reflections
a = 19.9172 (8) Åθ = 2.8–27.4°
b = 6.7515 (3) ŵ = 0.09 mm1
c = 10.6272 (4) ÅT = 150 K
V = 1429.05 (10) Å3Block, colourless
Z = 20.34 × 0.32 × 0.30 mm
Data collection top
Kappa-CCD
diffractometer
1651 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.039
Graphite monochromatorθmax = 27.4°, θmin = 2.8°
φ scans, and ω scans with κ offsetsh = 025
5749 measured reflectionsk = 08
1866 independent reflectionsl = 013
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)] = 0.033H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0314P)2 + 0.1756P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
1866 reflectionsΔρmax = 0.18 e Å3
179 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (6)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.62577 (7)0.9186 (2)0.50960 (12)0.0400 (4)
O20.62733 (7)1.2289 (2)0.43812 (13)0.0374 (3)
O30.65546 (7)0.57514 (19)0.01536 (12)0.0343 (3)
O40.61878 (7)0.87170 (19)0.07562 (12)0.0352 (3)
C110.68604 (8)0.9935 (3)0.31603 (15)0.0230 (4)
C120.63932 (8)0.9680 (3)0.19689 (15)0.0225 (4)
C130.68919 (8)0.8636 (3)0.10426 (15)0.0229 (4)
C140.73503 (9)0.7327 (3)0.18549 (16)0.0298 (4)
C150.72182 (9)0.7929 (3)0.32362 (16)0.0299 (4)
C160.64384 (8)1.0388 (3)0.43182 (16)0.0265 (4)
C170.73782 (9)1.1590 (3)0.29821 (18)0.0305 (4)
C180.65359 (8)0.7524 (3)0.00040 (16)0.0254 (4)
C190.61184 (10)1.1622 (3)0.14505 (18)0.0332 (4)
C1100.58050 (9)0.8275 (3)0.22665 (18)0.0326 (4)
N10.53977 (7)0.6366 (2)0.22287 (14)0.0247 (3)
N20.54616 (7)0.3815 (2)0.38512 (13)0.0244 (3)
C10.58487 (8)0.5177 (3)0.30423 (17)0.0254 (4)
C20.49408 (9)0.7492 (3)0.30460 (16)0.0259 (4)
C30.50000.50000.1446 (2)0.0272 (5)
C40.50000.50000.4635 (2)0.0274 (5)
H20.60261.24790.50090.056*
H40.59510.80320.12440.053*
H130.71760.96830.06440.027*
H14A0.72430.59100.17250.036*
H14B0.78270.75480.16330.036*
H15A0.76460.80500.37050.036*
H15B0.69310.69360.36610.036*
H17A0.76571.16960.37390.046*
H17B0.76631.12840.22560.046*
H17C0.71461.28480.28380.046*
H19A0.58701.23160.21130.050*
H19B0.64911.24540.11630.050*
H19C0.58171.13460.07420.050*
H11A0.55400.80550.15030.049*
H11B0.59810.70060.25700.049*
H11C0.55200.88690.29160.049*
H1A0.61610.44030.25090.030*
H1B0.61190.60750.35760.030*
H2A0.52060.84020.35810.031*
H2B0.46370.83040.25190.031*
H3A0.53050.42270.08980.033*0.50
H3B0.46950.57730.08980.033*0.50
H4A0.52640.58950.51830.033*0.50
H4B0.47360.41050.51830.033*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0498 (8)0.0401 (8)0.0300 (7)0.0015 (7)0.0140 (7)0.0056 (6)
O20.0465 (8)0.0335 (7)0.0322 (7)0.0078 (6)0.0176 (6)0.0025 (6)
O30.0428 (8)0.0249 (7)0.0354 (7)0.0005 (6)0.0041 (6)0.0066 (5)
O40.0454 (8)0.0275 (7)0.0325 (7)0.0031 (6)0.0166 (6)0.0035 (6)
C110.0225 (7)0.0255 (9)0.0210 (7)0.0010 (7)0.0012 (6)0.0016 (7)
C120.0204 (7)0.0234 (9)0.0236 (8)0.0011 (6)0.0010 (6)0.0008 (7)
C130.0226 (7)0.0234 (9)0.0227 (8)0.0007 (7)0.0007 (6)0.0025 (7)
C140.0291 (8)0.0308 (10)0.0296 (9)0.0082 (8)0.0027 (7)0.0050 (8)
C150.0302 (8)0.0339 (10)0.0255 (9)0.0085 (8)0.0014 (7)0.0002 (8)
C160.0240 (8)0.0314 (10)0.0240 (8)0.0009 (7)0.0020 (7)0.0018 (8)
C170.0254 (8)0.0376 (10)0.0285 (8)0.0067 (8)0.0040 (7)0.0064 (8)
C180.0258 (8)0.0257 (9)0.0246 (8)0.0026 (7)0.0009 (7)0.0009 (7)
C190.0390 (9)0.0298 (10)0.0308 (9)0.0095 (8)0.0056 (8)0.0008 (8)
C1100.0236 (8)0.0394 (11)0.0348 (10)0.0044 (8)0.0038 (8)0.0018 (9)
N10.0259 (7)0.0232 (7)0.0250 (7)0.0019 (6)0.0024 (6)0.0034 (6)
N20.0242 (7)0.0243 (8)0.0249 (7)0.0018 (6)0.0016 (6)0.0026 (6)
C10.0199 (7)0.0262 (9)0.0301 (8)0.0004 (7)0.0004 (7)0.0010 (8)
C20.0284 (8)0.0184 (8)0.0307 (8)0.0005 (7)0.0010 (8)0.0002 (8)
C30.0322 (12)0.0310 (14)0.0185 (10)0.0023 (11)0.0000.000
C40.0320 (12)0.0322 (14)0.0179 (11)0.0009 (11)0.0000.000
Geometric parameters (Å, º) top
O1—C161.213 (2)C17—H17B0.98
O2—C161.327 (2)C17—H17C0.98
O2—H20.84C19—H19A0.98
O3—C181.209 (2)C19—H19B0.98
O4—C181.335 (2)C19—H19C0.98
O4—H40.84C110—H11A0.98
C11—C161.521 (2)C110—H11B0.98
C11—C151.532 (3)C110—H11C0.98
C11—C171.533 (2)N1—C21.470 (2)
C11—C121.581 (2)N1—C31.473 (2)
C12—C191.524 (2)N1—C11.483 (2)
C12—C1101.540 (2)N2—C2i1.468 (2)
C12—C131.566 (2)N2—C11.476 (2)
C13—C181.511 (2)N2—C41.4764 (19)
C13—C141.537 (2)C1—H1A0.99
C13—H131.00C1—H1B0.99
C14—C151.546 (2)C2—H2A0.99
C14—H14A0.99C2—H2B0.99
C14—H14B0.99C3—H3A0.99
C15—H15A0.99C3—H3B0.99
C15—H15B0.99C4—H4A0.99
C17—H17A0.98C4—H4B0.99
C16—O2—H2109.5O4—C18—C13112.70 (15)
C18—O4—H4109.5C12—C19—H19A109.5
C16—C11—C15113.10 (15)C12—C19—H19B109.5
C16—C11—C17108.96 (14)H19A—C19—H19B109.5
C15—C11—C17109.75 (14)C12—C19—H19C109.5
C16—C11—C12110.15 (13)H19A—C19—H19C109.5
C15—C11—C12102.70 (14)H19B—C19—H19C109.5
C17—C11—C12112.12 (14)C12—C110—H11A109.5
C19—C12—C110109.33 (14)C12—C110—H11B109.5
C19—C12—C13112.82 (14)H11A—C110—H11B109.5
C110—C12—C13109.53 (14)C12—C110—H11C109.5
C19—C12—C11114.04 (14)H11A—C110—H11C109.5
C110—C12—C11110.50 (14)H11B—C110—H11C109.5
C13—C12—C11100.32 (12)C2—N1—C3108.95 (12)
C18—C13—C14113.78 (14)C2—N1—C1108.09 (13)
C18—C13—C12112.65 (13)C3—N1—C1108.41 (12)
C14—C13—C12106.42 (13)C2i—N2—C1108.68 (14)
C18—C13—H13107.9C2i—N2—C4108.36 (11)
C14—C13—H13107.9C1—N2—C4108.46 (12)
C12—C13—H13107.9N2—C1—N1111.13 (12)
C13—C14—C15106.32 (14)N2—C1—H1A109.4
C13—C14—H14A110.5N1—C1—H1A109.4
C15—C14—H14A110.5N2—C1—H1B109.4
C13—C14—H14B110.5N1—C1—H1B109.4
C15—C14—H14B110.5H1A—C1—H1B108.0
H14A—C14—H14B108.7N2i—C2—N1111.81 (13)
C11—C15—C14105.17 (14)N2i—C2—H2A109.3
C11—C15—H15A110.7N1—C2—H2A109.3
C14—C15—H15A110.7N2i—C2—H2B109.3
C11—C15—H15B110.7N1—C2—H2B109.3
C14—C15—H15B110.7H2A—C2—H2B107.9
H15A—C15—H15B108.8N1—C3—N1i111.24 (19)
O1—C16—O2122.64 (16)N1—C3—H3A109.4
O1—C16—C11125.47 (17)N1i—C3—H3A109.4
O2—C16—C11111.87 (15)N1—C3—H3B109.4
C11—C17—H17A109.5N1i—C3—H3B109.4
C11—C17—H17B109.5H3A—C3—H3B108.0
H17A—C17—H17B109.5N2—C4—N2i111.26 (18)
C11—C17—H17C109.5N2—C4—H4A109.4
H17A—C17—H17C109.5N2i—C4—H4A109.4
H17B—C17—H17C109.5N2—C4—H4B109.4
O3—C18—O4121.96 (16)N2i—C4—H4B109.4
O3—C18—C13125.33 (16)H4A—C4—H4B108.0
C16—C11—C12—C1975.15 (19)C15—C11—C16—O116.9 (2)
C15—C11—C12—C19164.11 (14)C17—C11—C16—O1139.22 (18)
C17—C11—C12—C1946.37 (19)C12—C11—C16—O197.4 (2)
C16—C11—C12—C11048.5 (2)C15—C11—C16—O2164.22 (15)
C15—C11—C12—C11072.27 (16)C17—C11—C16—O241.9 (2)
C17—C11—C12—C110170.00 (14)C12—C11—C16—O281.51 (18)
C16—C11—C12—C13164.00 (14)C14—C13—C18—O35.3 (2)
C15—C11—C12—C1343.26 (16)C12—C13—C18—O3115.95 (19)
C17—C11—C12—C1374.48 (17)C14—C13—C18—O4174.45 (14)
C19—C12—C13—C1879.55 (18)C12—C13—C18—O464.31 (19)
C110—C12—C13—C1842.48 (19)C2i—N2—C1—N158.60 (17)
C11—C12—C13—C18158.73 (14)C4—N2—C1—N159.00 (17)
C19—C12—C13—C14155.11 (14)C2—N1—C1—N258.94 (18)
C110—C12—C13—C1482.86 (16)C3—N1—C1—N259.01 (17)
C11—C12—C13—C1433.39 (16)C3—N1—C2—N2i58.28 (17)
C18—C13—C14—C15135.93 (15)C1—N1—C2—N2i59.32 (17)
C12—C13—C14—C1511.28 (18)C2—N1—C3—N1i58.52 (10)
C16—C11—C15—C14156.23 (14)C1—N1—C3—N1i58.89 (9)
C17—C11—C15—C1481.86 (17)C2i—N2—C4—N2i58.85 (10)
C12—C11—C15—C1437.54 (17)C1—N2—C4—N2i58.97 (10)
C13—C14—C15—C1116.52 (19)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N2ii0.841.882.684 (2)159
O4—H4···N10.841.892.728 (2)175
Symmetry code: (ii) x, y+1, z1.
(VI) (1R,3S)-Camphoric acid–piperazine (1/1) top
Crystal data top
C10H14O4·C4H12N2F(000) = 624
Mr = 286.37Dx = 1.228 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 1776 reflections
a = 19.1277 (4) Åθ = 2.9–26.0°
b = 7.5743 (6) ŵ = 0.09 mm1
c = 10.6920 (12) ÅT = 150 K
V = 1549.0 (2) Å3Block, colourless
Z = 40.35 × 0.30 × 0.28 mm
Data collection top
Kappa-CCD
diffractometer
1373 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.057
Graphite monochromatorθmax = 26.0°, θmin = 2.9°
φ scans, and ω scans with κ offsetsh = 023
6537 measured reflectionsk = 09
1776 independent reflectionsl = 013
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)] = 0.059H-atom parameters constrained
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0089P)2 + 1.4657P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max = 0.001
1776 reflectionsΔρmax = 0.18 e Å3
266 parametersΔρmin = 0.17 e Å3
50 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.2362 (2)0.3589 (5)0.3404 (4)0.0335 (10)
N40.2633 (2)0.6309 (5)0.1617 (4)0.0356 (11)
C20.1978 (3)0.5316 (6)0.3450 (5)0.0411 (13)
C30.2434 (3)0.6771 (7)0.2918 (6)0.0409 (13)
C50.3004 (2)0.4618 (6)0.1533 (5)0.0355 (12)
C60.2567 (3)0.3163 (6)0.2103 (6)0.0364 (12)
O110.1439 (10)0.167 (2)0.527 (2)0.042 (2)0.50
O120.1821 (8)0.066 (3)0.433 (3)0.0358 (17)0.50
O130.1405 (9)0.159 (2)0.547 (2)0.042 (2)0.50
O140.1767 (8)0.094 (3)0.460 (3)0.0358 (17)0.50
C110.0610 (6)0.0192 (12)0.3984 (8)0.034 (2)0.50
C120.0043 (5)0.0509 (8)0.4667 (7)0.025 (2)0.50
C130.0632 (6)0.0542 (11)0.4017 (10)0.034 (2)0.50
C140.0330 (6)0.2422 (11)0.3880 (15)0.056 (4)0.50
C150.0474 (6)0.2198 (11)0.3869 (15)0.050 (3)0.50
C160.1304 (7)0.032 (3)0.461 (2)0.0397 (16)0.50
C170.0726 (5)0.0463 (16)0.2631 (8)0.054 (3)0.50
C180.1338 (9)0.034 (3)0.469 (2)0.0397 (16)0.50
C190.0138 (7)0.2503 (10)0.4486 (13)0.049 (3)0.50
C1100.0009 (19)0.012 (5)0.6046 (7)0.043 (3)0.50
O210.6687 (7)1.1183 (18)0.0342 (16)0.0436 (18)0.50
O220.6456 (4)0.8406 (11)0.0144 (12)0.026 (2)0.50
O230.3211 (7)0.924 (2)0.0629 (16)0.0436 (18)0.50
O240.3570 (4)1.1564 (11)0.0504 (11)0.026 (2)0.50
C210.5608 (6)0.9749 (15)0.1126 (11)0.031 (5)0.50
C220.5017 (5)1.0712 (10)0.0412 (8)0.031 (2)0.50
C230.4338 (6)1.0033 (17)0.1039 (13)0.031 (5)0.50
C240.4509 (5)0.8085 (14)0.1349 (17)0.068 (4)0.50
C250.5312 (5)0.7878 (13)0.1302 (12)0.044 (3)0.50
C260.6312 (9)0.981 (2)0.043 (3)0.0263 (13)0.50
C270.5742 (5)1.0573 (17)0.2416 (9)0.062 (3)0.50
C280.3663 (9)1.036 (3)0.029 (2)0.0263 (13)0.50
C290.5095 (7)1.2719 (10)0.0434 (12)0.050 (3)0.50
C2100.500 (2)1.022 (5)0.0988 (7)0.039 (6)0.50
H1A0.27540.36530.38990.040*
H1B0.20800.27070.37130.040*
H4A0.22360.62540.11340.043*
H4B0.29130.71870.12980.043*
H2A0.18530.55980.43260.049*
H2B0.15410.52280.29590.049*
H3A0.21760.79040.29260.049*
H3B0.28600.69090.34370.049*
H5A0.34560.47040.19790.043*
H5B0.31020.43400.06450.043*
H6A0.21420.29850.15910.044*
H6B0.28370.20480.20970.044*
H130.06880.00460.31550.041*0.50
H14A0.04770.31740.45900.068*0.50
H14B0.04920.29730.30920.068*0.50
H15A0.06740.26610.30810.060*0.50
H15B0.06880.28390.45800.060*0.50
H17A0.03100.02060.21280.082*0.50
H17B0.08100.17400.26380.082*0.50
H17C0.11310.01400.22690.082*0.50
H19A0.05560.28960.49380.074*0.50
H19B0.02730.31250.48120.074*0.50
H19C0.01920.27630.35940.074*0.50
H11A0.00690.14050.60660.064*0.50
H11B0.04110.04460.64490.064*0.50
H11C0.04200.02010.64920.064*0.50
H230.42881.06730.18520.038*0.50
H24A0.43320.77810.21920.082*0.50
H24B0.42850.72910.07320.082*0.50
H25A0.54870.73510.20890.053*0.50
H25B0.54500.71090.05950.053*0.50
H27A0.59321.17660.23110.093*0.50
H27B0.60780.98460.28770.093*0.50
H27C0.53021.06340.28830.093*0.50
H9A0.51071.31310.13020.075*0.50
H9B0.46971.32590.00020.075*0.50
H9C0.55291.30550.00110.075*0.50
H21A0.49530.89430.10760.058*0.50
H21B0.54361.06110.13860.058*0.50
H21C0.46031.08110.13900.058*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.026 (2)0.036 (2)0.039 (3)0.0021 (18)0.000 (2)0.001 (2)
N40.032 (2)0.036 (2)0.039 (3)0.0023 (19)0.003 (2)0.003 (2)
C20.041 (3)0.048 (3)0.034 (3)0.003 (2)0.005 (3)0.003 (3)
C30.035 (3)0.042 (3)0.046 (3)0.004 (3)0.002 (3)0.002 (3)
C50.024 (2)0.033 (2)0.050 (3)0.004 (2)0.004 (2)0.005 (3)
C60.041 (3)0.029 (2)0.040 (3)0.000 (2)0.005 (3)0.009 (2)
O110.034 (2)0.041 (2)0.052 (6)0.0034 (18)0.001 (5)0.010 (6)
O120.040 (3)0.037 (6)0.030 (9)0.001 (3)0.008 (3)0.001 (3)
O130.034 (2)0.041 (2)0.052 (6)0.0034 (18)0.001 (5)0.010 (6)
O140.040 (3)0.037 (6)0.030 (9)0.001 (3)0.008 (3)0.001 (3)
C110.027 (3)0.042 (7)0.034 (3)0.017 (5)0.009 (4)0.001 (3)
C120.025 (4)0.025 (5)0.026 (4)0.004 (5)0.000 (5)0.003 (4)
C130.027 (3)0.042 (7)0.034 (3)0.017 (5)0.009 (4)0.001 (3)
C140.029 (6)0.038 (6)0.101 (11)0.003 (5)0.027 (7)0.029 (7)
C150.040 (7)0.029 (5)0.081 (9)0.016 (5)0.008 (6)0.016 (6)
C160.041 (3)0.050 (3)0.028 (4)0.004 (3)0.020 (8)0.006 (11)
C170.039 (5)0.090 (8)0.034 (5)0.013 (6)0.015 (4)0.009 (6)
C180.041 (3)0.050 (3)0.028 (4)0.004 (3)0.020 (8)0.006 (11)
C190.030 (7)0.027 (5)0.090 (10)0.002 (4)0.013 (7)0.004 (7)
C1100.030 (4)0.064 (8)0.035 (5)0.005 (6)0.022 (10)0.009 (12)
O210.040 (4)0.043 (6)0.047 (6)0.010 (4)0.006 (3)0.007 (3)
O220.0309 (18)0.0374 (18)0.009 (7)0.0021 (15)0.003 (2)0.002 (2)
O230.040 (4)0.043 (6)0.047 (6)0.010 (4)0.006 (3)0.007 (3)
O240.0309 (18)0.0374 (18)0.009 (7)0.0021 (15)0.003 (2)0.002 (2)
C210.020 (8)0.042 (8)0.032 (10)0.003 (6)0.009 (7)0.001 (8)
C220.028 (4)0.025 (4)0.040 (5)0.006 (4)0.006 (5)0.002 (4)
C230.032 (10)0.038 (8)0.025 (9)0.009 (7)0.004 (7)0.007 (7)
C240.031 (6)0.049 (6)0.123 (13)0.001 (5)0.011 (7)0.038 (8)
C250.031 (5)0.049 (5)0.053 (7)0.013 (5)0.000 (5)0.021 (5)
C260.016 (2)0.033 (4)0.030 (5)0.002 (2)0.002 (6)0.000 (7)
C270.042 (5)0.102 (10)0.041 (6)0.024 (6)0.021 (5)0.001 (6)
C280.016 (2)0.033 (4)0.030 (5)0.002 (2)0.002 (6)0.000 (7)
C290.051 (7)0.024 (4)0.075 (8)0.010 (5)0.002 (7)0.005 (6)
C2100.044 (5)0.042 (18)0.029 (4)0.002 (9)0.011 (9)0.003 (6)
Geometric parameters (Å, º) top
N1—C61.481 (7)C17—H17A0.98
N1—C21.500 (6)C17—H17B0.98
N1—H1A0.92C17—H17C0.98
N1—H1B0.92C19—H19A0.98
N4—C51.467 (5)C19—H19B0.98
N4—C31.484 (7)C19—H19C0.98
N4—H4A0.92C110—H11A0.98
N4—H4B0.92C110—H11B0.98
C2—C31.516 (7)C110—H11C0.98
C2—H2A0.99O21—C261.264 (7)
C2—H2B0.99O22—C261.260 (7)
C3—H3A0.99O23—C281.265 (7)
C3—H3B0.99O24—C281.255 (7)
C5—C61.512 (6)C21—C271.536 (10)
C5—H5A0.99C21—C251.538 (10)
C5—H5B0.99C21—C261.540 (8)
C6—H6A0.99C21—C221.546 (9)
C6—H6B0.99C22—C291.527 (8)
O11—C161.274 (7)C22—C2101.542 (9)
O12—C161.271 (7)C22—C231.549 (9)
O13—C181.273 (7)C23—C281.542 (8)
O14—C181.272 (7)C23—C241.547 (9)
C11—C161.534 (8)C23—H231.00
C11—C121.541 (9)C24—C251.544 (8)
C11—C151.546 (8)C24—H24A0.99
C11—C171.546 (9)C24—H24B0.99
C12—C191.534 (8)C25—H25A0.99
C12—C131.545 (8)C25—H25B0.99
C12—C1101.552 (10)C27—H27A0.98
C13—C181.536 (8)C27—H27B0.98
C13—C141.544 (9)C27—H27C0.98
C13—H131.00C29—H9A0.98
C14—C151.547 (8)C29—H9B0.98
C14—H14A0.99C29—H9C0.98
C14—H14B0.99C210—H21A0.98
C15—H15A0.99C210—H21B0.98
C15—H15B0.99C210—H21C0.98
C6—N1—C2110.5 (4)C11—C17—H17C109.5
C6—N1—H1A109.5H17A—C17—H17C109.5
C2—N1—H1A109.5H17B—C17—H17C109.5
C6—N1—H1B109.5O14—C18—O13123 (2)
C2—N1—H1B109.5O14—C18—C13127.5 (16)
H1A—N1—H1B108.1O13—C18—C13108.7 (16)
C5—N4—C3112.8 (4)C12—C19—H19A109.5
C5—N4—H4A109.0C12—C19—H19B109.5
C3—N4—H4A109.0H19A—C19—H19B109.5
C5—N4—H4B109.0C12—C19—H19C109.5
C3—N4—H4B109.0H19A—C19—H19C109.5
H4A—N4—H4B107.8H19B—C19—H19C109.5
N1—C2—C3109.9 (4)C12—C110—H11A109.5
N1—C2—H2A109.7C12—C110—H11B109.5
C3—C2—H2A109.7H11A—C110—H11B109.5
N1—C2—H2B109.7C12—C110—H11C109.5
C3—C2—H2B109.7H11A—C110—H11C109.5
H2A—C2—H2B108.2H11B—C110—H11C109.5
N4—C3—C2109.1 (4)C27—C21—C25109.0 (11)
N4—C3—H3A109.9C27—C21—C26106.0 (12)
C2—C3—H3A109.9C25—C21—C26114.3 (9)
N4—C3—H3B109.9C27—C21—C22111.9 (8)
C2—C3—H3B109.9C25—C21—C22103.1 (7)
H3A—C3—H3B108.3C26—C21—C22112.6 (15)
N4—C5—C6110.1 (4)C29—C22—C210104.8 (17)
N4—C5—H5A109.6C29—C22—C21113.1 (9)
C6—C5—H5A109.6C210—C22—C21112.4 (18)
N4—C5—H5B109.6C29—C22—C23113.9 (9)
C6—C5—H5B109.6C210—C22—C23108.8 (17)
H5A—C5—H5B108.2C21—C22—C23104.0 (6)
N1—C6—C5111.5 (4)C28—C23—C24116.2 (12)
N1—C6—H6A109.3C28—C23—C22115.0 (11)
C5—C6—H6A109.3C24—C23—C22103.4 (8)
N1—C6—H6B109.3C28—C23—H23107.2
C5—C6—H6B109.3C24—C23—H23107.2
H6A—C6—H6B108.0C22—C23—H23107.2
C16—C11—C12114.1 (9)C25—C24—C23107.4 (8)
C16—C11—C15115.4 (12)C25—C24—H24A110.2
C12—C11—C15103.9 (7)C23—C24—H24A110.2
C16—C11—C17101.6 (13)C25—C24—H24B110.2
C12—C11—C17116.7 (9)C23—C24—H24B110.2
C15—C11—C17105.4 (9)H24A—C24—H24B108.5
C19—C12—C11112.1 (9)C21—C25—C24106.1 (9)
C19—C12—C13111.3 (8)C21—C25—H25A110.5
C11—C12—C13101.5 (6)C24—C25—H25A110.5
C19—C12—C110115.5 (18)C21—C25—H25B110.5
C11—C12—C110107.0 (12)C24—C25—H25B110.5
C13—C12—C110108.4 (17)H25A—C25—H25B108.7
C18—C13—C14117.8 (10)O22—C26—O21122.4 (15)
C18—C13—C12112.3 (14)O22—C26—C21113.5 (10)
C14—C13—C12104.2 (8)O21—C26—C21123.9 (13)
C18—C13—H13107.4C21—C27—H27A109.5
C14—C13—H13107.4C21—C27—H27B109.5
C12—C13—H13107.4H27A—C27—H27B109.5
C13—C14—C15105.8 (8)C21—C27—H27C109.5
C13—C14—H14A110.6H27A—C27—H27C109.5
C15—C14—H14A110.6H27B—C27—H27C109.5
C13—C14—H14B110.6O24—C28—O23125.7 (16)
C15—C14—H14B110.6O24—C28—C23125.9 (10)
H14A—C14—H14B108.7O23—C28—C23108.3 (12)
C11—C15—C14105.9 (9)C22—C29—H9A109.5
C11—C15—H15A110.6C22—C29—H9B109.5
C14—C15—H15A110.6H9A—C29—H9B109.5
C11—C15—H15B110.6C22—C29—H9C109.5
C14—C15—H15B110.6H9A—C29—H9C109.5
H15A—C15—H15B108.7H9B—C29—H9C109.5
O12—C16—O11116 (2)C22—C210—H21A109.5
O12—C16—C11115.2 (15)C22—C210—H21B109.5
O11—C16—C11128.4 (16)H21A—C210—H21B109.5
C11—C17—H17A109.5C22—C210—H21C109.5
C11—C17—H17B109.5H21A—C210—H21C109.5
H17A—C17—H17B109.5H21B—C210—H21C109.5
C6—N1—C2—C358.1 (5)C12—C13—C18—O1481 (3)
C5—N4—C3—C258.2 (5)C14—C13—C18—O1328 (3)
N1—C2—C3—N457.9 (5)C12—C13—C18—O1393 (2)
C3—N4—C5—C656.3 (5)C27—C21—C22—C2947.2 (13)
C2—N1—C6—C556.5 (5)C25—C21—C22—C29164.2 (10)
N4—C5—C6—N154.9 (6)C26—C21—C22—C2972.2 (13)
C16—C11—C12—C1973.1 (15)C27—C21—C22—C210165.5 (17)
C15—C11—C12—C19160.4 (10)C25—C21—C22—C21077.5 (18)
C17—C11—C12—C1944.9 (12)C26—C21—C22—C21046.2 (17)
C16—C11—C12—C13168.0 (13)C27—C21—C22—C2376.9 (13)
C15—C11—C12—C1341.5 (10)C25—C21—C22—C2340.1 (10)
C17—C11—C12—C1374.0 (9)C26—C21—C22—C23163.8 (9)
C16—C11—C12—C11054 (2)C29—C22—C23—C2873.0 (19)
C15—C11—C12—C11072.1 (19)C210—C22—C23—C2843 (2)
C17—C11—C12—C110172.5 (18)C21—C22—C23—C28163.4 (15)
C19—C12—C13—C1870.9 (13)C29—C22—C23—C24159.2 (11)
C11—C12—C13—C18169.7 (10)C210—C22—C23—C2484 (2)
C110—C12—C13—C1857.2 (15)C21—C22—C23—C2435.7 (12)
C19—C12—C13—C14160.6 (10)C28—C23—C24—C25144.8 (17)
C11—C12—C13—C1441.2 (9)C22—C23—C24—C2517.8 (17)
C110—C12—C13—C1471.3 (15)C27—C21—C25—C2490.3 (13)
C18—C13—C14—C15150.2 (17)C26—C21—C25—C24151.3 (17)
C12—C13—C14—C1525.2 (14)C22—C21—C25—C2428.7 (14)
C16—C11—C15—C14152.0 (15)C23—C24—C25—C216.8 (19)
C12—C11—C15—C1426.3 (14)C27—C21—C26—O22136 (2)
C17—C11—C15—C1496.9 (13)C25—C21—C26—O2216 (3)
C13—C14—C15—C110.7 (17)C22—C21—C26—O22101 (2)
C12—C11—C16—O12158.4 (16)C27—C21—C26—O2150 (3)
C15—C11—C16—O1238 (3)C25—C21—C26—O21170 (2)
C17—C11—C16—O1275 (2)C22—C21—C26—O2173 (3)
C12—C11—C16—O1128 (3)C24—C23—C28—O24147 (2)
C15—C11—C16—O11148 (2)C22—C23—C28—O2426 (4)
C17—C11—C16—O1198 (3)C24—C23—C28—O2335 (3)
C14—C13—C18—O14158 (2)C22—C23—C28—O23156.5 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O11i0.921.802.70 (2)168
N1—H1A···O13ii0.921.752.65 (2)165
N1—H1B···O12iii0.921.762.64 (2)160
N1—H1B···O140.921.752.64 (3)162
N4—H4A···O22iv0.921.852.756 (12)169
N4—H4A···O24v0.921.702.598 (11)165
N4—H4B···O21vi0.921.782.677 (14)165
N4—H4B···O230.921.812.698 (15)163
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1/2, y+1/2, z+1; (iii) x, y, z; (iv) x1/2, y+3/2, z; (v) x+1/2, y1/2, z; (vi) x+1, y+2, z.
(VII) (1R,3S)-Camphoric acid–N,N'-dimethylpiperazine–water (3/1/2) top
Crystal data top
C10H16O4·2(C10H15O4)·(C6H16N2)·2H2OF(000) = 816
Mr = 750.91Dx = 1.218 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 2095 reflections
a = 13.5730 (4) Åθ = 3.0–25.0°
b = 22.0500 (8) ŵ = 0.09 mm1
c = 6.8417 (2) ÅT = 150 K
V = 2047.62 (11) Å3Plate, colourless
Z = 20.28 × 0.22 × 0.10 mm
Data collection top
Kappa-CCD
diffractometer
1634 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.061
Graphite monochromatorθmax = 25.0°, θmin = 3.0°
φ scans, and ω scans with κ offsetsh = 016
10832 measured reflectionsk = 026
2095 independent reflectionsl = 08
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0563P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2095 reflectionsΔρmax = 0.17 e Å3
279 parametersΔρmin = 0.16 e Å3
17 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.016 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O110.33237 (14)0.39238 (9)0.5336 (3)0.0391 (5)
O120.34266 (17)0.39076 (9)0.8532 (3)0.0472 (6)
O130.10923 (15)0.16156 (9)0.5115 (3)0.0399 (5)
O140.11203 (16)0.15307 (10)0.8359 (3)0.0453 (6)
C110.3414 (2)0.29374 (12)0.6922 (4)0.0327 (6)
C120.2407 (2)0.26648 (12)0.7631 (4)0.0326 (7)
C130.2500 (2)0.19960 (12)0.6895 (4)0.0340 (6)
C140.3101 (2)0.20236 (14)0.4985 (4)0.0456 (8)
C150.3521 (2)0.26696 (13)0.4854 (4)0.0400 (7)
C160.3382 (2)0.36310 (13)0.6930 (4)0.0345 (6)
C170.4296 (2)0.27338 (13)0.8176 (5)0.0433 (7)
C180.1510 (2)0.16958 (12)0.6659 (4)0.0345 (7)
C190.2248 (3)0.26972 (15)0.9846 (4)0.0487 (9)
C1100.1542 (2)0.29837 (14)0.6618 (5)0.0414 (7)
O210.2376 (7)0.4890 (5)0.2495 (11)0.041 (2)0.50
O220.1798 (7)0.5865 (4)0.294 (3)0.0442 (19)0.50
O230.2567 (8)0.4967 (5)0.2308 (11)0.041 (2)0.50
O240.1732 (7)0.4181 (4)0.340 (3)0.0442 (19)0.50
C210.0795 (8)0.5121 (4)0.1174 (11)0.0336 (13)0.50
C220.0141 (5)0.5132 (3)0.2474 (6)0.0314 (18)0.50
C230.0892 (8)0.4780 (4)0.1182 (12)0.0336 (13)0.50
C240.0279 (4)0.4240 (3)0.0435 (12)0.0500 (18)0.50
C250.0789 (4)0.4474 (3)0.0275 (9)0.0418 (15)0.50
C260.1775 (7)0.5314 (4)0.210 (4)0.039 (3)0.50
C270.0768 (5)0.5591 (3)0.0496 (10)0.0455 (17)0.50
C280.1785 (7)0.4703 (5)0.247 (4)0.039 (3)0.50
C290.0528 (5)0.5769 (3)0.2942 (13)0.061 (2)0.50
C2100.0077 (8)0.4807 (3)0.4411 (7)0.050 (3)0.50
N10.39397 (16)0.50789 (10)0.7269 (3)0.0317 (5)
C20.4539 (2)0.51920 (13)0.5473 (4)0.0340 (7)
C60.4541 (2)0.51950 (14)0.9034 (4)0.0413 (8)
C70.3028 (2)0.54518 (14)0.7305 (5)0.0417 (8)
O30.43824 (13)0.39526 (9)0.1984 (3)0.0380 (5)
H140.05520.13910.81730.068*
H130.28880.17610.78810.041*
H14A0.36420.17220.50130.055*
H14B0.26740.19370.38460.055*
H15A0.31450.29140.38940.048*
H15B0.42210.26600.44520.048*
H17A0.43280.22900.81940.065*
H17B0.42140.28850.95130.065*
H17C0.49060.28970.76190.065*
H19A0.27940.24931.05150.073*
H19B0.16270.24961.01840.073*
H19C0.22220.31231.02570.073*
H11A0.16540.29900.52040.062*
H11B0.14890.34010.71030.062*
H11C0.09310.27650.69010.062*
H220.23410.59140.35030.066*0.50
H240.22140.41470.41590.066*0.50
H230.10760.50410.00420.040*0.50
H24A0.03180.38960.13610.060*0.50
H24B0.05220.41030.08570.060*0.50
H25A0.12430.42040.10020.050*0.50
H25B0.09990.44870.11100.050*0.50
H27A0.01950.55130.13300.068*0.50
H27B0.07200.60000.00580.068*0.50
H27C0.13710.55580.12750.068*0.50
H29A0.06620.59860.17210.092*0.50
H29B0.11360.57360.37060.092*0.50
H29C0.00320.59910.36990.092*0.50
H21A0.03380.44010.41410.075*0.50
H21B0.05640.50400.51540.075*0.50
H21C0.05310.47720.51730.075*0.50
H10.37560.46730.72760.038*
H2A0.47220.56260.54120.041*
H2B0.41400.50960.43020.041*
H6A0.41460.51061.02160.050*
H6B0.47320.56280.90730.050*
H7A0.26390.53700.61270.063*
H7B0.32040.58830.73440.063*
H7C0.26390.53490.84650.063*
H310.41260.38870.31780.073*
H320.40040.38860.09240.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0374 (11)0.0382 (12)0.0417 (11)0.0003 (10)0.0017 (9)0.0109 (10)
O120.0632 (14)0.0332 (12)0.0451 (13)0.0030 (11)0.0188 (11)0.0072 (10)
O130.0482 (12)0.0387 (12)0.0328 (12)0.0079 (10)0.0016 (9)0.0041 (9)
O140.0441 (13)0.0538 (14)0.0378 (12)0.0172 (11)0.0030 (10)0.0042 (10)
C110.0345 (15)0.0286 (15)0.0351 (15)0.0060 (13)0.0048 (13)0.0011 (12)
C120.0382 (16)0.0286 (15)0.0310 (15)0.0061 (13)0.0021 (12)0.0046 (12)
C130.0370 (16)0.0281 (15)0.0369 (14)0.0033 (13)0.0031 (14)0.0038 (13)
C140.051 (2)0.0402 (19)0.0454 (19)0.0058 (15)0.0143 (15)0.0107 (15)
C150.0425 (17)0.0382 (17)0.0392 (17)0.0077 (15)0.0071 (13)0.0025 (14)
C160.0268 (14)0.0348 (16)0.0418 (16)0.0052 (13)0.0055 (13)0.0027 (14)
C170.0388 (17)0.0343 (16)0.0567 (19)0.0006 (14)0.0111 (15)0.0056 (15)
C180.0438 (17)0.0252 (15)0.0345 (16)0.0014 (13)0.0021 (13)0.0014 (13)
C190.061 (2)0.048 (2)0.0373 (17)0.0163 (17)0.0087 (15)0.0113 (15)
C1100.0317 (16)0.0351 (17)0.0575 (19)0.0004 (14)0.0018 (14)0.0050 (15)
O210.015 (3)0.057 (5)0.0507 (17)0.006 (4)0.0059 (18)0.003 (2)
O220.0340 (15)0.069 (2)0.029 (7)0.0017 (14)0.0003 (18)0.005 (2)
O230.015 (3)0.057 (5)0.0507 (17)0.006 (4)0.0059 (18)0.003 (2)
O240.0340 (15)0.069 (2)0.029 (7)0.0017 (14)0.0003 (18)0.005 (2)
C210.026 (2)0.043 (3)0.0325 (15)0.004 (2)0.013 (4)0.006 (4)
C220.019 (5)0.040 (6)0.035 (2)0.005 (3)0.004 (3)0.006 (3)
C230.026 (2)0.043 (3)0.0325 (15)0.004 (2)0.013 (4)0.006 (4)
C240.040 (4)0.052 (4)0.058 (4)0.013 (4)0.018 (4)0.019 (4)
C250.034 (3)0.048 (4)0.043 (3)0.001 (3)0.003 (3)0.015 (3)
C260.0354 (18)0.069 (2)0.013 (8)0.0038 (17)0.002 (3)0.001 (3)
C270.036 (4)0.050 (4)0.051 (4)0.010 (3)0.001 (3)0.008 (3)
C280.0354 (18)0.069 (2)0.013 (8)0.0038 (17)0.002 (3)0.001 (3)
C290.044 (4)0.040 (4)0.099 (6)0.004 (3)0.016 (4)0.020 (4)
C2100.041 (4)0.082 (8)0.027 (2)0.010 (7)0.003 (3)0.003 (3)
N10.0285 (12)0.0261 (12)0.0406 (13)0.0002 (10)0.0011 (10)0.0008 (10)
C20.0326 (16)0.0421 (18)0.0273 (12)0.0061 (13)0.0001 (12)0.0030 (12)
C60.0421 (19)0.053 (2)0.0285 (13)0.0095 (16)0.0001 (13)0.0014 (14)
C70.0327 (16)0.0395 (18)0.0530 (18)0.0059 (14)0.0035 (14)0.0044 (15)
O30.0366 (11)0.0452 (12)0.0321 (10)0.0002 (9)0.0042 (8)0.0023 (9)
Geometric parameters (Å, º) top
O11—C161.270 (3)C21—C221.551 (8)
O12—C161.256 (3)C21—C251.555 (9)
O13—C181.212 (3)C22—C291.534 (6)
O14—C181.328 (3)C22—C2101.535 (6)
O14—H140.84C22—C231.556 (8)
C11—C161.530 (4)C23—C281.511 (12)
C11—C171.539 (4)C23—C241.540 (8)
C11—C151.540 (4)C23—H231.00
C11—C121.570 (4)C24—C251.542 (7)
C12—C191.533 (4)C24—H24A0.99
C12—C1101.534 (4)C24—H24B0.99
C12—C131.564 (4)C25—H25A0.99
C13—C181.507 (4)C25—H25B0.99
C13—C141.541 (4)C27—H27A0.98
C13—H131.00C27—H27B0.98
C14—C151.537 (4)C27—H27C0.98
C14—H14A0.99C29—H29A0.98
C14—H14B0.99C29—H29B0.98
C15—H15A0.99C29—H29C0.98
C15—H15B0.99C210—H21A0.98
C17—H17A0.98C210—H21B0.98
C17—H17B0.98C210—H21C0.98
C17—H17C0.98N1—C61.480 (3)
C19—H19A0.98N1—C71.486 (3)
C19—H19B0.98N1—C21.494 (3)
C19—H19C0.98N1—H10.93
C110—H11A0.98C2—C2i1.512 (6)
C110—H11B0.98C2—H2A0.99
C110—H11C0.98C2—H2B0.99
O21—C261.270 (11)C6—C6i1.513 (6)
O22—C261.343 (11)C6—H6A0.99
O22—H220.84C6—H6B0.99
O23—C281.216 (11)C7—H7A0.98
O24—C281.313 (11)C7—H7B0.98
O24—H240.84C7—H7C0.98
C21—C261.534 (10)O3—H310.90
C21—C271.542 (8)O3—H320.90
C18—O14—H14109.5C28—C23—C24122.7 (8)
C16—C11—C17108.2 (2)C28—C23—C22104.4 (9)
C16—C11—C15112.9 (2)C24—C23—C22102.7 (6)
C17—C11—C15109.1 (3)C28—C23—H23108.7
C16—C11—C12110.9 (2)C24—C23—H23108.7
C17—C11—C12113.1 (2)C22—C23—H23108.7
C15—C11—C12102.6 (2)C23—C24—C25105.8 (6)
C19—C12—C110108.5 (3)C23—C24—H24A110.6
C19—C12—C13112.0 (2)C25—C24—H24A110.6
C110—C12—C13110.4 (2)C23—C24—H24B110.6
C19—C12—C11114.2 (2)C25—C24—H24B110.6
C110—C12—C11110.6 (2)H24A—C24—H24B108.7
C13—C12—C11101.0 (2)C24—C25—C21106.5 (6)
C18—C13—C14113.5 (2)C24—C25—H25A110.4
C18—C13—C12112.1 (2)C21—C25—H25A110.4
C14—C13—C12106.2 (2)C24—C25—H25B110.4
C18—C13—H13108.3C21—C25—H25B110.4
C14—C13—H13108.3H25A—C25—H25B108.6
C12—C13—H13108.3O21—C26—O22124.1 (12)
C15—C14—C13106.4 (2)O21—C26—C21116.2 (10)
C15—C14—H14A110.4O22—C26—C21116.6 (10)
C13—C14—H14A110.4C21—C27—H27A109.5
C15—C14—H14B110.4C21—C27—H27B109.5
C13—C14—H14B110.4H27A—C27—H27B109.5
H14A—C14—H14B108.6C21—C27—H27C109.5
C14—C15—C11105.5 (2)H27A—C27—H27C109.5
C14—C15—H15A110.6H27B—C27—H27C109.5
C11—C15—H15A110.6O23—C28—O24120.9 (10)
C14—C15—H15B110.6O23—C28—C23126.2 (17)
C11—C15—H15B110.6O24—C28—C23109.6 (10)
H15A—C15—H15B108.8C22—C29—H29A109.5
O12—C16—O11120.4 (2)C22—C29—H29B109.5
O12—C16—C11119.2 (3)H29A—C29—H29B109.5
O11—C16—C11120.4 (3)C22—C29—H29C109.5
C11—C17—H17A109.5H29A—C29—H29C109.5
C11—C17—H17B109.5H29B—C29—H29C109.5
H17A—C17—H17B109.5C22—C210—H21A109.5
C11—C17—H17C109.5C22—C210—H21B109.5
H17A—C17—H17C109.5H21A—C210—H21B109.5
H17B—C17—H17C109.5C22—C210—H21C109.5
O13—C18—O14122.5 (3)H21A—C210—H21C109.5
O13—C18—C13125.1 (3)H21B—C210—H21C109.5
O14—C18—C13112.5 (2)C6—N1—C7110.5 (2)
C12—C19—H19A109.5C6—N1—C2110.0 (2)
C12—C19—H19B109.5C7—N1—C2112.0 (2)
H19A—C19—H19B109.5C6—N1—H1108.1
C12—C19—H19C109.5C7—N1—H1108.1
H19A—C19—H19C109.5C2—N1—H1108.1
H19B—C19—H19C109.5N1—C2—C2i110.93 (18)
C12—C110—H11A109.5N1—C2—H2A109.5
C12—C110—H11B109.5C2i—C2—H2A109.5
H11A—C110—H11B109.5N1—C2—H2B109.5
C12—C110—H11C109.5C2i—C2—H2B109.5
H11A—C110—H11C109.5H2A—C2—H2B108.0
H11B—C110—H11C109.5N1—C6—C6i110.8 (2)
C26—C21—C2798.1 (10)N1—C6—H6A109.5
C26—C21—C22118.0 (10)C6i—C6—H6A109.5
C27—C21—C22113.3 (7)N1—C6—H6B109.5
C26—C21—C25115.0 (8)C6i—C6—H6B109.5
C27—C21—C25108.9 (6)H6A—C6—H6B108.1
C22—C21—C25103.7 (6)N1—C7—H7A109.5
C29—C22—C210108.2 (5)N1—C7—H7B109.5
C29—C22—C21114.4 (6)H7A—C7—H7B109.5
C210—C22—C21109.3 (6)N1—C7—H7C109.5
C29—C22—C23110.5 (5)H7A—C7—H7C109.5
C210—C22—C23112.6 (7)H7B—C7—H7C109.5
C21—C22—C23101.7 (4)H31—O3—H32119.0
C16—C11—C12—C1976.4 (3)C25—C21—C22—C29158.7 (6)
C17—C11—C12—C1945.4 (3)C26—C21—C22—C21048.7 (9)
C15—C11—C12—C19162.8 (2)C27—C21—C22—C210162.4 (7)
C16—C11—C12—C11046.4 (3)C25—C21—C22—C21079.7 (7)
C17—C11—C12—C110168.1 (2)C26—C21—C22—C23168.0 (6)
C15—C11—C12—C11074.5 (3)C27—C21—C22—C2378.3 (9)
C16—C11—C12—C13163.2 (2)C25—C21—C22—C2339.5 (7)
C17—C11—C12—C1375.0 (3)C29—C22—C23—C2865.1 (9)
C15—C11—C12—C1342.4 (3)C210—C22—C23—C2856.1 (8)
C19—C12—C13—C1880.6 (3)C21—C22—C23—C28172.9 (6)
C110—C12—C13—C1840.4 (3)C29—C22—C23—C24165.8 (6)
C11—C12—C13—C18157.4 (2)C210—C22—C23—C2473.0 (7)
C19—C12—C13—C14154.9 (3)C21—C22—C23—C2443.8 (7)
C110—C12—C13—C1484.1 (3)C28—C23—C24—C25148.0 (13)
C11—C12—C13—C1432.9 (3)C22—C23—C24—C2531.3 (8)
C18—C13—C14—C15134.7 (3)C23—C24—C25—C216.8 (9)
C12—C13—C14—C1511.0 (3)C26—C21—C25—C24150.8 (12)
C13—C14—C15—C1116.1 (3)C27—C21—C25—C24100.3 (7)
C16—C11—C15—C14156.1 (2)C22—C21—C25—C2420.5 (7)
C17—C11—C15—C1483.5 (3)C27—C21—C26—O21132.8 (17)
C12—C11—C15—C1436.7 (3)C22—C21—C26—O21105.3 (18)
C17—C11—C16—O1249.9 (4)C25—C21—C26—O2118 (2)
C15—C11—C16—O12170.8 (3)C27—C21—C26—O2266.4 (16)
C12—C11—C16—O1274.7 (3)C22—C21—C26—O2255.5 (17)
C17—C11—C16—O11129.2 (3)C25—C21—C26—O22178.4 (11)
C15—C11—C16—O118.3 (4)C24—C23—C28—O23136.4 (13)
C12—C11—C16—O11106.3 (3)C22—C23—C28—O23107.8 (18)
C14—C13—C18—O1317.8 (4)C24—C23—C28—O2423 (2)
C12—C13—C18—O13102.5 (3)C22—C23—C28—O2492.8 (13)
C14—C13—C18—O14163.2 (2)C6—N1—C2—C2i56.6 (3)
C12—C13—C18—O1476.5 (3)C7—N1—C2—C2i180.0 (3)
C26—C21—C22—C2972.8 (9)C7—N1—C6—C6i178.6 (3)
C27—C21—C22—C2940.9 (8)C2—N1—C6—C6i57.3 (3)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O110.932.202.989 (3)142
N1—H1···O120.931.952.811 (3)154
O3—H31···O110.901.842.708 (3)162
O3—H32···O12ii0.901.822.696 (3)166
O14—H14···O3iii0.841.762.599 (3)174
O22—H22···O11iv0.841.872.683 (18)164
O24—H24···O110.841.782.598 (17)165
Symmetry codes: (ii) x, y, z1; (iii) x1/2, y+1/2, z+1; (iv) x, y+1, z.
 

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