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(1
R,3
S)-Camphoric acid [(1
R,3
S)-1,2,2,-trimethylcyclopentane-1,3-dicarboxylic acid, C
10H
16O
4] forms adducts with a range of amines in which the acid component may be the neutral molecule, the mono-anion (C
10H
15O
4)
− or the di-anion (C
10H
14O
4)
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 C
10H
16O
4 and anionic (C
10H
15O
4)
− 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
CCDC references: 205190; 205191; 205192; 205193; 205194; 205195; 205196
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) (1
R,3S)-Camphoric acid
top
Crystal data top
C10H16O4 | F(000) = 432 |
Mr = 200.23 | Dx = 1.219 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2608 reflections |
a = 7.7206 (3) Å | θ = 2.8–27.5° |
b = 11.6677 (5) Å | µ = 0.09 mm−1 |
c = 12.5830 (5) Å | T = 150 K |
β = 105.653 (2)° | Needle, colourless |
V = 1091.46 (8) Å3 | 0.30 × 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 tube | Rint = 0.043 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
φ scans, and ω scans with κ offsets | h = 0→10 |
9392 measured reflections | k = 0→15 |
2608 independent reflections | l = −16→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-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 reflections | Δρmax = 0.19 e Å−3 |
264 parameters | Δρmin = −0.14 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (6) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O11 | 0.4517 (2) | 0.5569 (2) | 0.08314 (14) | 0.0471 (5) | |
O12 | 0.7099 (2) | 0.6090 (2) | 0.20146 (13) | 0.0457 (5) | |
O13 | 0.7994 (3) | 0.5148 (3) | −0.27972 (18) | 0.0726 (9) | |
O14 | 1.0477 (2) | 0.6000 (2) | −0.18300 (17) | 0.0584 (6) | |
C11 | 0.6569 (3) | 0.6756 (2) | 0.01621 (19) | 0.0353 (6) | |
C12 | 0.8105 (3) | 0.6072 (2) | −0.01901 (18) | 0.0330 (5) | |
C13 | 0.7780 (3) | 0.6499 (2) | −0.14025 (18) | 0.0354 (6) | |
C14 | 0.5731 (3) | 0.6496 (3) | −0.18629 (19) | 0.0416 (6) | |
C15 | 0.5031 (3) | 0.6894 (3) | −0.0909 (2) | 0.0502 (8) | |
C16 | 0.5949 (3) | 0.6078 (3) | 0.10246 (18) | 0.0358 (6) | |
C17 | 0.7210 (4) | 0.7945 (3) | 0.0639 (3) | 0.0534 (8) | |
C18 | 0.8748 (3) | 0.5808 (3) | −0.20740 (19) | 0.0412 (7) | |
C19 | 0.9998 (3) | 0.6336 (3) | 0.0521 (2) | 0.0467 (7) | |
C110 | 0.7804 (4) | 0.4771 (3) | −0.0168 (2) | 0.0508 (7) | |
O21 | 0.2139 (2) | 0.4672 (2) | 0.70262 (14) | 0.0493 (6) | |
O22 | −0.0379 (3) | 0.3933 (3) | 0.59666 (18) | 0.0749 (9) | |
O23 | 0.5762 (2) | 0.4908 (2) | 0.34303 (14) | 0.0460 (5) | |
O24 | 0.3219 (2) | 0.4370 (2) | 0.22186 (14) | 0.0459 (5) | |
C21 | 0.2304 (3) | 0.3461 (2) | 0.54952 (18) | 0.0335 (5) | |
C22 | 0.2194 (3) | 0.4210 (2) | 0.44317 (17) | 0.0295 (5) | |
C23 | 0.3740 (3) | 0.3650 (2) | 0.40330 (18) | 0.0315 (5) | |
C24 | 0.5233 (3) | 0.3405 (3) | 0.5086 (2) | 0.0417 (6) | |
C25 | 0.4331 (3) | 0.3334 (3) | 0.6028 (2) | 0.0385 (6) | |
C26 | 0.1367 (3) | 0.4081 (3) | 0.62449 (19) | 0.0403 (6) | |
C28 | 0.4354 (3) | 0.4370 (2) | 0.32135 (18) | 0.0327 (5) | |
C27 | 0.1436 (4) | 0.2278 (3) | 0.5199 (2) | 0.0453 (7) | |
C29 | 0.0376 (3) | 0.4157 (3) | 0.3566 (2) | 0.0451 (7) | |
C210 | 0.2665 (4) | 0.5461 (2) | 0.4745 (2) | 0.0418 (6) | |
H12 | 0.6657 | 0.5734 | 0.2459 | 0.069* | |
H14 | 1.0940 | 0.5584 | −0.2224 | 0.088* | |
H13 | 0.8206 | 0.7310 | −0.1382 | 0.043* | |
H14A | 0.5350 | 0.7025 | −0.2498 | 0.050* | |
H14B | 0.5287 | 0.5716 | −0.2104 | 0.050* | |
H15A | 0.3981 | 0.6427 | −0.0868 | 0.060* | |
H15B | 0.4652 | 0.7706 | −0.1012 | 0.060* | |
H17A | 0.6207 | 0.8354 | 0.0806 | 0.080* | |
H17B | 0.7644 | 0.8383 | 0.0098 | 0.080* | |
H17C | 0.8188 | 0.7854 | 0.1316 | 0.080* | |
H19A | 1.0085 | 0.6142 | 0.1292 | 0.070* | |
H19B | 1.0253 | 0.7153 | 0.0466 | 0.070* | |
H19C | 1.0872 | 0.5881 | 0.0263 | 0.070* | |
H11A | 0.8648 | 0.4377 | −0.0502 | 0.076* | |
H11B | 0.6568 | 0.4589 | −0.0585 | 0.076* | |
H11C | 0.8003 | 0.4516 | 0.0598 | 0.076* | |
H22 | −0.0822 | 0.4278 | 0.6418 | 0.112* | |
H24 | 0.3644 | 0.4765 | 0.1791 | 0.069* | |
H23 | 0.3297 | 0.2902 | 0.3675 | 0.038* | |
H24A | 0.6138 | 0.4027 | 0.5226 | 0.050* | |
H24B | 0.5841 | 0.2673 | 0.5015 | 0.050* | |
H25A | 0.4771 | 0.3955 | 0.6570 | 0.046* | |
H25B | 0.4595 | 0.2588 | 0.6413 | 0.046* | |
H27A | 0.1525 | 0.1841 | 0.5877 | 0.068* | |
H27B | 0.2062 | 0.1866 | 0.4734 | 0.068* | |
H27C | 0.0167 | 0.2373 | 0.4798 | 0.068* | |
H29A | −0.0576 | 0.4392 | 0.3901 | 0.068* | |
H29B | 0.0150 | 0.3371 | 0.3288 | 0.068* | |
H29C | 0.0388 | 0.4674 | 0.2954 | 0.068* | |
H21A | 0.2685 | 0.5898 | 0.4083 | 0.063* | |
H21B | 0.3850 | 0.5500 | 0.5280 | 0.063* | |
H21C | 0.1759 | 0.5788 | 0.5074 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O11 | 0.0339 (10) | 0.0740 (15) | 0.0329 (9) | −0.0109 (10) | 0.0080 (7) | 0.0054 (9) |
O12 | 0.0378 (9) | 0.0706 (14) | 0.0284 (8) | −0.0097 (10) | 0.0085 (7) | 0.0077 (9) |
O13 | 0.0372 (11) | 0.124 (2) | 0.0628 (13) | −0.0242 (13) | 0.0240 (10) | −0.0523 (15) |
O14 | 0.0311 (10) | 0.0863 (17) | 0.0620 (12) | −0.0145 (11) | 0.0196 (9) | −0.0337 (12) |
C11 | 0.0279 (12) | 0.0473 (16) | 0.0327 (12) | 0.0042 (11) | 0.0116 (9) | 0.0038 (11) |
C12 | 0.0295 (12) | 0.0426 (15) | 0.0299 (11) | 0.0023 (11) | 0.0131 (9) | 0.0038 (10) |
C13 | 0.0303 (12) | 0.0466 (16) | 0.0306 (12) | −0.0067 (11) | 0.0104 (9) | 0.0006 (10) |
C14 | 0.0312 (12) | 0.0625 (19) | 0.0309 (12) | −0.0054 (13) | 0.0078 (10) | 0.0032 (12) |
C15 | 0.0326 (13) | 0.085 (2) | 0.0337 (13) | 0.0105 (15) | 0.0110 (10) | 0.0124 (14) |
C16 | 0.0288 (12) | 0.0533 (16) | 0.0275 (11) | 0.0039 (12) | 0.0115 (9) | −0.0004 (11) |
C17 | 0.063 (2) | 0.0463 (18) | 0.0588 (18) | 0.0072 (15) | 0.0294 (15) | 0.0033 (14) |
C18 | 0.0291 (12) | 0.0619 (19) | 0.0358 (13) | −0.0122 (13) | 0.0143 (10) | −0.0055 (12) |
C19 | 0.0313 (13) | 0.071 (2) | 0.0380 (13) | 0.0057 (13) | 0.0089 (11) | 0.0051 (13) |
C110 | 0.0599 (18) | 0.0429 (17) | 0.0596 (17) | 0.0039 (14) | 0.0335 (15) | 0.0064 (14) |
O21 | 0.0323 (9) | 0.0788 (16) | 0.0397 (10) | −0.0101 (10) | 0.0147 (8) | −0.0172 (10) |
O22 | 0.0283 (10) | 0.137 (3) | 0.0648 (14) | −0.0227 (13) | 0.0223 (9) | −0.0511 (15) |
O23 | 0.0334 (9) | 0.0705 (14) | 0.0341 (9) | −0.0141 (10) | 0.0089 (7) | 0.0061 (9) |
O24 | 0.0398 (10) | 0.0644 (14) | 0.0326 (9) | −0.0150 (10) | 0.0084 (7) | 0.0046 (9) |
C21 | 0.0303 (12) | 0.0415 (15) | 0.0303 (11) | −0.0077 (11) | 0.0108 (9) | −0.0003 (10) |
C22 | 0.0261 (11) | 0.0328 (13) | 0.0307 (11) | −0.0001 (10) | 0.0099 (8) | 0.0009 (10) |
C23 | 0.0326 (12) | 0.0327 (13) | 0.0329 (11) | 0.0029 (10) | 0.0151 (10) | −0.0009 (10) |
C24 | 0.0326 (14) | 0.0516 (17) | 0.0432 (13) | 0.0111 (13) | 0.0138 (11) | 0.0097 (12) |
C25 | 0.0309 (13) | 0.0515 (16) | 0.0327 (12) | −0.0003 (12) | 0.0081 (10) | 0.0027 (11) |
C26 | 0.0273 (12) | 0.0658 (19) | 0.0297 (11) | −0.0091 (13) | 0.0109 (9) | −0.0028 (12) |
C28 | 0.0294 (12) | 0.0418 (14) | 0.0291 (11) | 0.0010 (11) | 0.0117 (9) | −0.0015 (10) |
C27 | 0.0470 (16) | 0.0438 (17) | 0.0459 (14) | −0.0133 (13) | 0.0140 (12) | 0.0070 (12) |
C29 | 0.0285 (12) | 0.066 (2) | 0.0386 (13) | 0.0009 (13) | 0.0056 (10) | 0.0099 (13) |
C210 | 0.0417 (14) | 0.0333 (14) | 0.0570 (16) | 0.0055 (12) | 0.0244 (12) | −0.0002 (12) |
Geometric parameters (Å, º) top
O11—C16 | 1.221 (3) | O21—C26 | 1.217 (3) |
O12—C16 | 1.320 (3) | O22—C26 | 1.309 (3) |
O12—H12 | 0.84 | O22—H22 | 0.84 |
O13—C18 | 1.214 (3) | O23—C28 | 1.221 (3) |
O14—C18 | 1.306 (3) | O24—C28 | 1.320 (3) |
O14—H14 | 0.84 | O24—H24 | 0.84 |
C11—C16 | 1.521 (3) | C21—C26 | 1.518 (3) |
C11—C17 | 1.538 (4) | C21—C25 | 1.535 (3) |
C11—C15 | 1.545 (3) | C21—C27 | 1.535 (4) |
C11—C12 | 1.588 (3) | C21—C22 | 1.581 (3) |
C12—C19 | 1.525 (4) | C22—C29 | 1.528 (3) |
C12—C110 | 1.538 (4) | C22—C210 | 1.530 (4) |
C12—C13 | 1.559 (3) | C22—C23 | 1.558 (3) |
C13—C18 | 1.505 (4) | C23—C28 | 1.503 (3) |
C13—C14 | 1.531 (3) | C23—C24 | 1.530 (4) |
C13—H13 | 1.00 | C23—H23 | 1.00 |
C14—C15 | 1.516 (4) | C24—C25 | 1.531 (3) |
C14—H14A | 0.99 | C24—H24A | 0.99 |
C14—H14B | 0.99 | C24—H24B | 0.99 |
C15—H15A | 0.99 | C25—H25A | 0.99 |
C15—H15B | 0.99 | C25—H25B | 0.99 |
C17—H17A | 0.98 | C27—H27A | 0.98 |
C17—H17B | 0.98 | C27—H27B | 0.98 |
C17—H17C | 0.98 | C27—H27C | 0.98 |
C19—H19A | 0.98 | C29—H29A | 0.98 |
C19—H19B | 0.98 | C29—H29B | 0.98 |
C19—H19C | 0.98 | C29—H29C | 0.98 |
C110—H11A | 0.98 | C210—H21A | 0.98 |
C110—H11B | 0.98 | C210—H21B | 0.98 |
C110—H11C | 0.98 | C210—H21C | 0.98 |
| | | |
C16—O12—H12 | 109.5 | C26—O22—H22 | 109.5 |
C18—O14—H14 | 109.5 | C28—O24—H24 | 109.5 |
C16—C11—C17 | 108.7 (2) | C26—C21—C25 | 112.04 (19) |
C16—C11—C15 | 111.1 (2) | C26—C21—C27 | 109.2 (2) |
C17—C11—C15 | 109.7 (3) | C25—C21—C27 | 110.2 (2) |
C16—C11—C12 | 109.9 (2) | C26—C21—C22 | 109.7 (2) |
C17—C11—C12 | 112.1 (2) | C25—C21—C22 | 103.83 (17) |
C15—C11—C12 | 105.3 (2) | C27—C21—C22 | 111.79 (19) |
C19—C12—C110 | 108.3 (2) | C29—C22—C210 | 109.3 (2) |
C19—C12—C13 | 112.7 (2) | C29—C22—C23 | 112.94 (19) |
C110—C12—C13 | 110.4 (2) | C210—C22—C23 | 109.49 (19) |
C19—C12—C11 | 113.9 (2) | C29—C22—C21 | 114.2 (2) |
C110—C12—C11 | 111.3 (2) | C210—C22—C21 | 110.74 (19) |
C13—C12—C11 | 100.23 (19) | C23—C22—C21 | 99.79 (18) |
C18—C13—C14 | 113.9 (2) | C28—C23—C24 | 113.3 (2) |
C18—C13—C12 | 113.9 (2) | C28—C23—C22 | 113.4 (2) |
C14—C13—C12 | 104.26 (18) | C24—C23—C22 | 105.26 (18) |
C18—C13—H13 | 108.2 | C28—C23—H23 | 108.2 |
C14—C13—H13 | 108.2 | C24—C23—H23 | 108.2 |
C12—C13—H13 | 108.2 | C22—C23—H23 | 108.2 |
C15—C14—C13 | 104.6 (2) | C23—C24—C25 | 106.7 (2) |
C15—C14—H14A | 110.8 | C23—C24—H24A | 110.4 |
C13—C14—H14A | 110.8 | C25—C24—H24A | 110.4 |
C15—C14—H14B | 110.8 | C23—C24—H24B | 110.4 |
C13—C14—H14B | 110.8 | C25—C24—H24B | 110.4 |
H14A—C14—H14B | 108.9 | H24A—C24—H24B | 108.6 |
C14—C15—C11 | 107.7 (2) | C24—C25—C21 | 106.22 (19) |
C14—C15—H15A | 110.2 | C24—C25—H25A | 110.5 |
C11—C15—H15A | 110.2 | C21—C25—H25A | 110.5 |
C14—C15—H15B | 110.2 | C24—C25—H25B | 110.5 |
C11—C15—H15B | 110.2 | C21—C25—H25B | 110.5 |
H15A—C15—H15B | 108.5 | H25A—C25—H25B | 108.7 |
O11—C16—O12 | 122.4 (2) | O21—C26—O22 | 122.4 (2) |
O11—C16—C11 | 123.6 (2) | O21—C26—C21 | 124.1 (2) |
O12—C16—C11 | 114.0 (2) | O22—C26—C21 | 113.6 (2) |
C11—C17—H17A | 109.5 | O23—C28—O24 | 122.4 (2) |
C11—C17—H17B | 109.5 | O23—C28—C23 | 124.1 (2) |
H17A—C17—H17B | 109.5 | O24—C28—C23 | 113.5 (2) |
C11—C17—H17C | 109.5 | C21—C27—H27A | 109.5 |
H17A—C17—H17C | 109.5 | C21—C27—H27B | 109.5 |
H17B—C17—H17C | 109.5 | H27A—C27—H27B | 109.5 |
O13—C18—O14 | 122.5 (2) | C21—C27—H27C | 109.5 |
O13—C18—C13 | 123.4 (2) | H27A—C27—H27C | 109.5 |
O14—C18—C13 | 114.0 (2) | H27B—C27—H27C | 109.5 |
C12—C19—H19A | 109.5 | C22—C29—H29A | 109.5 |
C12—C19—H19B | 109.5 | C22—C29—H29B | 109.5 |
H19A—C19—H19B | 109.5 | H29A—C29—H29B | 109.5 |
C12—C19—H19C | 109.5 | C22—C29—H29C | 109.5 |
H19A—C19—H19C | 109.5 | H29A—C29—H29C | 109.5 |
H19B—C19—H19C | 109.5 | H29B—C29—H29C | 109.5 |
C12—C110—H11A | 109.5 | C22—C210—H21A | 109.5 |
C12—C110—H11B | 109.5 | C22—C210—H21B | 109.5 |
H11A—C110—H11B | 109.5 | H21A—C210—H21B | 109.5 |
C12—C110—H11C | 109.5 | C22—C210—H21C | 109.5 |
H11A—C110—H11C | 109.5 | H21A—C210—H21C | 109.5 |
H11B—C110—H11C | 109.5 | H21B—C210—H21C | 109.5 |
| | | |
C16—C11—C12—C19 | −89.0 (3) | C26—C21—C22—C29 | −78.2 (3) |
C17—C11—C12—C19 | 32.0 (3) | C25—C21—C22—C29 | 161.9 (2) |
C15—C11—C12—C19 | 151.2 (2) | C27—C21—C22—C29 | 43.1 (3) |
C16—C11—C12—C110 | 33.8 (3) | C26—C21—C22—C210 | 45.8 (3) |
C17—C11—C12—C110 | 154.7 (2) | C25—C21—C22—C210 | −74.1 (2) |
C15—C11—C12—C110 | −86.0 (3) | C27—C21—C22—C210 | 167.1 (2) |
C16—C11—C12—C13 | 150.5 (2) | C26—C21—C22—C23 | 161.06 (19) |
C17—C11—C12—C13 | −88.6 (2) | C25—C21—C22—C23 | 41.2 (2) |
C15—C11—C12—C13 | 30.7 (3) | C27—C21—C22—C23 | −77.6 (2) |
C19—C12—C13—C18 | 71.9 (3) | C29—C22—C23—C28 | 74.7 (3) |
C110—C12—C13—C18 | −49.2 (3) | C210—C22—C23—C28 | −47.4 (3) |
C11—C12—C13—C18 | −166.7 (2) | C21—C22—C23—C28 | −163.60 (19) |
C19—C12—C13—C14 | −163.3 (2) | C29—C22—C23—C24 | −160.9 (2) |
C110—C12—C13—C14 | 75.5 (3) | C210—C22—C23—C24 | 77.1 (2) |
C11—C12—C13—C14 | −41.9 (3) | C21—C22—C23—C24 | −39.2 (2) |
C18—C13—C14—C15 | 162.5 (3) | C28—C23—C24—C25 | 147.5 (2) |
C12—C13—C14—C15 | 37.8 (3) | C22—C23—C24—C25 | 23.0 (3) |
C13—C14—C15—C11 | −17.6 (3) | C23—C24—C25—C21 | 3.6 (3) |
C16—C11—C15—C14 | −127.7 (3) | C26—C21—C25—C24 | −146.6 (2) |
C17—C11—C15—C14 | 112.0 (3) | C27—C21—C25—C24 | 91.5 (3) |
C12—C11—C15—C14 | −8.8 (3) | C22—C21—C25—C24 | −28.3 (3) |
C17—C11—C16—O11 | 131.0 (3) | C25—C21—C26—O21 | 18.5 (4) |
C15—C11—C16—O11 | 10.2 (4) | C27—C21—C26—O21 | 140.9 (3) |
C12—C11—C16—O11 | −106.0 (3) | C22—C21—C26—O21 | −96.2 (3) |
C17—C11—C16—O12 | −48.7 (3) | C25—C21—C26—O22 | −162.2 (3) |
C15—C11—C16—O12 | −169.5 (2) | C27—C21—C26—O22 | −39.8 (3) |
C12—C11—C16—O12 | 74.3 (3) | C22—C21—C26—O22 | 83.1 (3) |
C14—C13—C18—O13 | −12.2 (4) | C24—C23—C28—O23 | −14.4 (4) |
C12—C13—C18—O13 | 107.2 (3) | C22—C23—C28—O23 | 105.5 (3) |
C14—C13—C18—O14 | 166.2 (3) | C24—C23—C28—O24 | 165.5 (2) |
C12—C13—C18—O14 | −74.4 (3) | C22—C23—C28—O24 | −74.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O23 | 0.84 | 1.83 | 2.670 (2) | 178 |
O14—H14···O21i | 0.84 | 1.83 | 2.667 (3) | 175 |
O22—H22···O13ii | 0.84 | 1.82 | 2.657 (3) | 171 |
O24—H24···O11 | 0.84 | 1.80 | 2.637 (2) | 178 |
Symmetry codes: (i) x+1, y, z−1; (ii) x−1, y, z+1. |
(II) (1
R,3S)-Camphoric acid–4,4'-bipyridyl (1/1)
top
Crystal data top
C10H16O4·C10H8N2 | Dx = 1.318 Mg m−3 |
Mr = 356.41 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P3121 | Cell parameters from 1103 reflections |
Hall symbol: P 31 2" | θ = 3.5–26.0° |
a = 6.7302 (10) Å | µ = 0.09 mm−1 |
c = 34.345 (7) Å | T = 150 K |
V = 1347.3 (4) Å3 | Block, colourless |
Z = 3 | 0.35 × 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 tube | Rint = 0.034 |
Graphite monochromator | θmax = 26.0°, θmin = 3.5° |
φ scans, and ω scans with κ offsets | h = 0→8 |
4738 measured reflections | k = −6→0 |
1103 independent reflections | l = −41→42 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-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 reflections | Δρmax = 0.15 e Å−3 |
164 parameters | Δρmin = −0.17 e Å−3 |
14 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (4) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N11 | 0.2756 (3) | 0.8545 (3) | 0.03353 (6) | 0.0397 (5) | |
C12 | 0.3888 (5) | 0.7900 (4) | 0.05797 (7) | 0.0439 (7) | |
C13 | 0.5044 (4) | 0.6790 (4) | 0.04619 (7) | 0.0410 (6) | |
C14 | 0.5065 (4) | 0.6285 (4) | 0.00682 (7) | 0.0341 (6) | |
C15 | 0.3904 (4) | 0.6957 (4) | −0.01853 (7) | 0.0379 (6) | |
C16 | 0.2791 (4) | 0.8076 (4) | −0.00424 (7) | 0.0385 (6) | |
O1 | −0.0775 (13) | 0.987 (3) | 0.2607 (3) | 0.0315 (9) | 0.50 |
O2 | −0.4008 (18) | 0.814 (3) | 0.2332 (6) | 0.0415 (16) | 0.50 |
O3 | 0.0638 (12) | 1.0160 (18) | 0.0781 (3) | 0.0315 (9) | 0.50 |
O4 | 0.4268 (18) | 1.2500 (16) | 0.1072 (6) | 0.0415 (16) | 0.50 |
C1 | −0.0779 (19) | 1.143 (2) | 0.1960 (3) | 0.023 (2) | 0.50 |
C2 | 0.0694 (7) | 1.0754 (7) | 0.16886 (14) | 0.0259 (11) | 0.50 |
C3 | 0.116 (2) | 1.239 (2) | 0.1333 (3) | 0.032 (3) | 0.50 |
C4 | −0.1100 (17) | 1.2362 (17) | 0.1263 (3) | 0.031 (2) | 0.50 |
C5 | −0.2383 (8) | 1.1667 (8) | 0.16558 (11) | 0.0308 (10) | 0.50 |
C6 | −0.202 (2) | 0.971 (2) | 0.2284 (4) | 0.0330 (10) | 0.50 |
C7 | 0.0732 (19) | 1.3800 (17) | 0.2158 (3) | 0.033 (2) | 0.50 |
C8 | 0.222 (2) | 1.170 (3) | 0.1018 (5) | 0.0330 (10) | 0.50 |
C9 | 0.2941 (8) | 1.1174 (9) | 0.18698 (13) | 0.0372 (12) | 0.50 |
C10 | −0.0720 (9) | 0.8244 (7) | 0.15685 (13) | 0.0359 (12) | 0.50 |
H12 | 0.3894 | 0.8227 | 0.0849 | 0.053* | |
H13 | 0.5818 | 0.6373 | 0.0647 | 0.049* | |
H15 | 0.3869 | 0.6652 | −0.0456 | 0.045* | |
H16 | 0.2019 | 0.8531 | −0.0222 | 0.046* | |
H3A | 0.2322 | 1.3981 | 0.1417 | 0.038* | 0.50 |
H4A | −0.2009 | 1.1238 | 0.1058 | 0.037* | 0.50 |
H4B | −0.0808 | 1.3897 | 0.1182 | 0.037* | 0.50 |
H5A | −0.3834 | 1.0189 | 0.1629 | 0.037* | 0.50 |
H5B | −0.2754 | 1.2849 | 0.1742 | 0.037* | 0.50 |
H7A | 0.1556 | 1.4966 | 0.1958 | 0.049* | 0.50 |
H7B | 0.1839 | 1.3713 | 0.2332 | 0.049* | 0.50 |
H7C | −0.0246 | 1.4213 | 0.2308 | 0.049* | 0.50 |
H9A | 0.2609 | 1.0157 | 0.2094 | 0.056* | 0.50 |
H9B | 0.3836 | 1.2775 | 0.1955 | 0.056* | 0.50 |
H9C | 0.3820 | 1.0860 | 0.1677 | 0.056* | 0.50 |
H10A | −0.2181 | 0.7957 | 0.1457 | 0.054* | 0.50 |
H10B | −0.1018 | 0.7263 | 0.1797 | 0.054* | 0.50 |
H10C | 0.0129 | 0.7897 | 0.1374 | 0.054* | 0.50 |
H1 | −0.1616 | 0.8287 | 0.2752 | 0.040* | 0.50 |
H3 | 0.1616 | 0.9903 | 0.0581 | 0.040* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0343 (12) | 0.0318 (12) | 0.0499 (13) | 0.0141 (10) | 0.0106 (10) | 0.0006 (10) |
C12 | 0.0523 (17) | 0.0384 (14) | 0.0426 (14) | 0.0238 (13) | 0.0161 (12) | 0.0056 (12) |
C13 | 0.0431 (15) | 0.0371 (14) | 0.0453 (14) | 0.0220 (12) | 0.0091 (12) | 0.0039 (12) |
C14 | 0.0238 (12) | 0.0237 (12) | 0.0466 (14) | 0.0058 (10) | 0.0058 (10) | −0.0035 (10) |
C15 | 0.0289 (13) | 0.0339 (13) | 0.0455 (14) | 0.0117 (11) | −0.0033 (11) | −0.0120 (11) |
C16 | 0.0293 (13) | 0.0339 (14) | 0.0492 (14) | 0.0134 (12) | −0.0028 (11) | −0.0059 (12) |
O1 | 0.0303 (11) | 0.028 (4) | 0.040 (3) | 0.0167 (13) | 0.0034 (13) | −0.0028 (13) |
O2 | 0.019 (2) | 0.044 (2) | 0.053 (6) | 0.010 (2) | −0.008 (3) | −0.001 (3) |
O3 | 0.0303 (11) | 0.028 (4) | 0.040 (3) | 0.0167 (13) | 0.0034 (13) | −0.0028 (13) |
O4 | 0.019 (2) | 0.044 (2) | 0.053 (6) | 0.010 (2) | −0.008 (3) | −0.001 (3) |
C1 | 0.023 (4) | 0.025 (5) | 0.025 (4) | 0.016 (4) | 0.002 (3) | 0.005 (3) |
C2 | 0.027 (3) | 0.027 (2) | 0.023 (2) | 0.013 (2) | 0.000 (3) | −0.001 (2) |
C3 | 0.030 (5) | 0.028 (5) | 0.037 (5) | 0.014 (4) | −0.003 (4) | 0.007 (4) |
C4 | 0.034 (4) | 0.036 (6) | 0.028 (4) | 0.021 (4) | 0.002 (3) | 0.005 (3) |
C5 | 0.027 (2) | 0.029 (3) | 0.039 (3) | 0.016 (2) | 0.002 (2) | 0.001 (2) |
C6 | 0.024 (2) | 0.029 (4) | 0.044 (2) | 0.012 (4) | 0.0007 (19) | −0.010 (4) |
C7 | 0.032 (4) | 0.025 (4) | 0.036 (5) | 0.010 (3) | 0.009 (3) | −0.003 (3) |
C8 | 0.024 (2) | 0.029 (4) | 0.044 (2) | 0.012 (4) | 0.0007 (19) | −0.010 (4) |
C9 | 0.030 (3) | 0.054 (3) | 0.034 (3) | 0.026 (2) | −0.005 (2) | 0.000 (2) |
C10 | 0.051 (4) | 0.030 (3) | 0.031 (3) | 0.023 (3) | 0.002 (2) | 0.003 (2) |
Geometric parameters (Å, º) top
N11—C16 | 1.338 (3) | C2—C10 | 1.524 (5) |
N11—C12 | 1.343 (3) | C2—C9 | 1.525 (5) |
C12—C13 | 1.382 (3) | C2—C3 | 1.568 (8) |
C12—H12 | 0.95 | C3—C8 | 1.494 (8) |
C13—C14 | 1.396 (3) | C3—C4 | 1.529 (9) |
C13—H13 | 0.95 | C3—H3A | 1.00 |
C14—C15 | 1.388 (3) | C4—C5 | 1.541 (8) |
C14—C14i | 1.498 (4) | C4—H4A | 0.99 |
C15—C16 | 1.391 (3) | C4—H4B | 0.99 |
C15—H15 | 0.95 | C5—H5A | 0.99 |
C16—H16 | 0.95 | C5—H5B | 0.99 |
O1—C6 | 1.363 (8) | C7—H7A | 0.98 |
O1—H1 | 1.0471 | C7—H7B | 0.98 |
O2—C6 | 1.231 (8) | C7—H7C | 0.98 |
O3—C8 | 1.327 (8) | C9—H9A | 0.98 |
O3—H3 | 1.0249 | C9—H9B | 0.98 |
O4—C8 | 1.219 (9) | C9—H9C | 0.98 |
C1—C6 | 1.523 (8) | C10—H10A | 0.98 |
C1—C7 | 1.552 (8) | C10—H10B | 0.98 |
C1—C5 | 1.566 (10) | C10—H10C | 0.98 |
C1—C2 | 1.586 (9) | | |
| | | |
C16—N11—C12 | 116.8 (2) | C3—C4—C5 | 105.6 (7) |
N11—C12—C13 | 123.7 (2) | C3—C4—H4A | 110.6 |
N11—C12—H12 | 118.1 | C5—C4—H4A | 110.6 |
C13—C12—H12 | 118.1 | C3—C4—H4B | 110.6 |
C12—C13—C14 | 119.5 (2) | C5—C4—H4B | 110.6 |
C12—C13—H13 | 120.3 | H4A—C4—H4B | 108.7 |
C14—C13—H13 | 120.3 | C4—C5—C1 | 107.7 (7) |
C15—C14—C13 | 116.9 (2) | C4—C5—H5A | 110.2 |
C15—C14—C14i | 122.3 (3) | C1—C5—H5A | 110.2 |
C13—C14—C14i | 120.8 (3) | C4—C5—H5B | 110.2 |
C14—C15—C16 | 119.9 (2) | C1—C5—H5B | 110.2 |
C14—C15—H15 | 120.1 | H5A—C5—H5B | 108.5 |
C16—C15—H15 | 120.1 | O2—C6—O1 | 108.7 (14) |
N11—C16—C15 | 123.2 (2) | O2—C6—C1 | 134.3 (11) |
N11—C16—H16 | 118.4 | O1—C6—C1 | 116.9 (13) |
C15—C16—H16 | 118.4 | C1—C7—H7A | 109.5 |
C6—O1—H1 | 107.9 | C1—C7—H7B | 109.5 |
C8—O3—H3 | 102.2 | H7A—C7—H7B | 109.5 |
C6—C1—C7 | 107.0 (8) | C1—C7—H7C | 109.5 |
C6—C1—C5 | 114.9 (9) | H7A—C7—H7C | 109.5 |
C7—C1—C5 | 108.7 (9) | H7B—C7—H7C | 109.5 |
C6—C1—C2 | 113.2 (11) | O4—C8—O3 | 136.6 (11) |
C7—C1—C2 | 111.7 (7) | O4—C8—C3 | 111.2 (10) |
C5—C1—C2 | 101.5 (6) | O3—C8—C3 | 111.6 (14) |
C10—C2—C9 | 109.2 (4) | C2—C9—H9A | 109.5 |
C10—C2—C3 | 111.3 (6) | C2—C9—H9B | 109.5 |
C9—C2—C3 | 110.9 (6) | H9A—C9—H9B | 109.5 |
C10—C2—C1 | 110.2 (5) | C2—C9—H9C | 109.5 |
C9—C2—C1 | 114.3 (5) | H9A—C9—H9C | 109.5 |
C3—C2—C1 | 100.8 (4) | H9B—C9—H9C | 109.5 |
C8—C3—C4 | 120.5 (9) | C2—C10—H10A | 109.5 |
C8—C3—C2 | 107.5 (12) | C2—C10—H10B | 109.5 |
C4—C3—C2 | 105.4 (7) | H10A—C10—H10B | 109.5 |
C8—C3—H3A | 107.6 | C2—C10—H10C | 109.5 |
C4—C3—H3A | 107.6 | H10A—C10—H10C | 109.5 |
C2—C3—H3A | 107.6 | H10B—C10—H10C | 109.5 |
| | | |
C16—N11—C12—C13 | −0.5 (3) | C10—C2—C3—C4 | 75.8 (9) |
N11—C12—C13—C14 | 0.0 (4) | C9—C2—C3—C4 | −162.5 (7) |
C12—C13—C14—C15 | 0.3 (3) | C1—C2—C3—C4 | −41.1 (10) |
C12—C13—C14—C14i | −179.46 (16) | C8—C3—C4—C5 | 145.5 (12) |
C13—C14—C15—C16 | 0.0 (3) | C2—C3—C4—C5 | 23.9 (11) |
C14i—C14—C15—C16 | 179.72 (14) | C3—C4—C5—C1 | 3.2 (11) |
C12—N11—C16—C15 | 0.7 (3) | C6—C1—C5—C4 | −150.7 (10) |
C14—C15—C16—N11 | −0.5 (3) | C7—C1—C5—C4 | 89.6 (7) |
C6—C1—C2—C10 | 47.3 (9) | C2—C1—C5—C4 | −28.2 (9) |
C7—C1—C2—C10 | 168.1 (7) | C7—C1—C6—O2 | 136 (2) |
C5—C1—C2—C10 | −76.3 (7) | C5—C1—C6—O2 | 15 (3) |
C6—C1—C2—C9 | −76.0 (9) | C2—C1—C6—O2 | −101 (3) |
C7—C1—C2—C9 | 44.8 (10) | C7—C1—C6—O1 | −42.3 (18) |
C5—C1—C2—C9 | 160.4 (5) | C5—C1—C6—O1 | −163.0 (11) |
C6—C1—C2—C3 | 165.0 (6) | C2—C1—C6—O1 | 81.2 (16) |
C7—C1—C2—C3 | −74.2 (11) | C4—C3—C8—O4 | 157.9 (15) |
C5—C1—C2—C3 | 41.4 (9) | C2—C3—C8—O4 | −81 (2) |
C10—C2—C3—C8 | −54.0 (9) | C4—C3—C8—O3 | −30 (2) |
C9—C2—C3—C8 | 67.8 (10) | C2—C3—C8—O3 | 91.1 (15) |
C1—C2—C3—C8 | −170.8 (7) | | |
Symmetry code: (i) y, x, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N11ii | 1.05 | 1.69 | 2.732 (16) | 175 |
O3—H3···N11 | 1.02 | 1.68 | 2.666 (10) | 159 |
C15—H15···O2iii | 0.95 | 2.44 | 3.293 (19) | 149 |
C15—H15···O4iv | 0.95 | 2.53 | 3.425 (19) | 156 |
Symmetry codes: (ii) −x, −x+y, −z+1/3; (iii) −x+y−1, −x, z−1/3; (iv) y−1, x, −z. |
(III) (1
R,3S)-Camphoric acid–1,2-bis(4-pyridyl)ethane (1/1)
top
Crystal data top
C12H12N2·C10H16O4 | Z = 4 |
Mr = 384.46 | F(000) = 824 |
Triclinic, P1 | Dx = 1.258 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5318 (2) Å | Cell parameters from 9230 reflections |
b = 10.3775 (2) Å | θ = 2.6–27.4° |
c = 23.3884 (5) Å | µ = 0.09 mm−1 |
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 tube | Rint = 0.064 |
Graphite monochromator | θmax = 27.4°, θmin = 2.6° |
φ scans, and ω scans with κ offsets | h = 0→11 |
34201 measured reflections | k = −13→13 |
9230 independent reflections | l = −30→29 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-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 reflections | Δρmax = 0.26 e Å−3 |
1272 parameters | Δρmin = −0.20 e Å−3 |
241 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.032 (4) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 1.9906 (4) | 1.0925 (4) | 1.12261 (14) | 0.0530 (9) | 0.8469 (14) |
O2A | 1.8735 (4) | 0.9515 (3) | 1.16787 (14) | 0.0417 (7) | 0.8469 (14) |
O3A | 2.1254 (10) | 1.2821 (5) | 1.3935 (3) | 0.0418 (12) | 0.8469 (14) |
O4A | 2.2848 (10) | 1.3950 (4) | 1.3481 (2) | 0.0362 (12) | 0.8469 (14) |
C1A | 2.1204 (4) | 1.0486 (4) | 1.21304 (15) | 0.0297 (8) | 0.8469 (14) |
C2A | 2.1244 (5) | 1.1915 (4) | 1.24833 (17) | 0.0332 (9) | 0.8469 (14) |
C3A | 2.2298 (6) | 1.1757 (4) | 1.30526 (18) | 0.0308 (9) | 0.8469 (14) |
C4A | 2.1864 (6) | 1.0391 (5) | 1.3176 (3) | 0.0409 (12) | 0.8469 (14) |
C5A | 2.1005 (5) | 0.9642 (4) | 1.26064 (17) | 0.0404 (9) | 0.8469 (14) |
C6A | 1.9906 (5) | 1.0328 (4) | 1.16321 (17) | 0.0345 (9) | 0.8469 (14) |
C7A | 2.2761 (5) | 1.0161 (4) | 1.18631 (18) | 0.0456 (10) | 0.8469 (14) |
C8A | 2.2073 (6) | 1.2870 (4) | 1.35438 (18) | 0.0294 (9) | 0.8469 (14) |
C9A | 1.9575 (5) | 1.2298 (5) | 1.2627 (2) | 0.0462 (11) | 0.8469 (14) |
C10A | 2.1911 (6) | 1.2946 (4) | 1.2169 (2) | 0.0468 (11) | 0.8469 (14) |
O1U | 2.129 (6) | 1.259 (4) | 1.3922 (14) | 0.0425 (9)* | 0.1531 (14) |
O2U | 2.287 (6) | 1.378 (3) | 1.3552 (18) | 0.0425 (9)* | 0.1531 (14) |
O3U | 2.1814 (19) | 1.1454 (16) | 1.1087 (6) | 0.0425 (9)* | 0.1531 (14) |
O4U | 1.9840 (18) | 1.0191 (19) | 1.1232 (8) | 0.0425 (9)* | 0.1531 (14) |
C1U | 2.231 (2) | 1.159 (2) | 1.3029 (8) | 0.0425 (9)* | 0.1531 (14) |
C2U | 2.109 (2) | 1.165 (2) | 1.2493 (8) | 0.0425 (9)* | 0.1531 (14) |
C3U | 2.1893 (19) | 1.073 (2) | 1.2016 (6) | 0.0425 (9)* | 0.1531 (14) |
C4U | 2.367 (2) | 1.111 (2) | 1.2123 (7) | 0.0425 (9)* | 0.1531 (14) |
C5U | 2.395 (2) | 1.167 (2) | 1.2782 (8) | 0.0425 (9)* | 0.1531 (14) |
C6U | 2.210 (4) | 1.266 (3) | 1.3527 (7) | 0.0425 (9)* | 0.1531 (14) |
C7U | 2.220 (4) | 1.029 (3) | 1.3255 (17) | 0.0425 (9)* | 0.1531 (14) |
C8U | 2.1192 (18) | 1.0851 (16) | 1.1415 (6) | 0.0425 (9)* | 0.1531 (14) |
C9U | 2.094 (3) | 1.303 (2) | 1.2328 (11) | 0.0425 (9)* | 0.1531 (14) |
C10U | 1.940 (2) | 1.114 (2) | 1.2567 (11) | 0.0425 (9)* | 0.1531 (14) |
N1B | 1.6234 (4) | 0.9914 (3) | 1.09700 (15) | 0.0357 (7) | 0.8469 (14) |
C12B | 1.6029 (5) | 1.1194 (4) | 1.0986 (2) | 0.0405 (10) | 0.8469 (14) |
C13B | 1.4718 (5) | 1.1702 (4) | 1.0725 (2) | 0.0386 (10) | 0.8469 (14) |
C14B | 1.3513 (5) | 1.0861 (4) | 1.04244 (17) | 0.0335 (8) | 0.8469 (14) |
C15B | 1.3730 (5) | 0.9530 (4) | 1.04047 (17) | 0.0331 (8) | 0.8469 (14) |
C16B | 1.5081 (5) | 0.9098 (4) | 1.06798 (17) | 0.0355 (9) | 0.8469 (14) |
C17B | 1.2006 (5) | 1.1317 (4) | 1.01468 (18) | 0.0360 (9) | 0.8469 (14) |
N2B | 0.7449 (4) | 1.3958 (3) | 0.94272 (14) | 0.0314 (7) | 0.8469 (14) |
C22B | 0.7681 (5) | 1.3986 (4) | 1.00028 (18) | 0.0371 (9) | 0.8469 (14) |
C23B | 0.9056 (5) | 1.3589 (4) | 1.02788 (18) | 0.0370 (9) | 0.8469 (14) |
C24B | 1.0288 (5) | 1.3170 (4) | 0.99547 (18) | 0.0343 (9) | 0.8469 (14) |
C25B | 1.0047 (5) | 1.3112 (4) | 0.93530 (19) | 0.0352 (9) | 0.8469 (14) |
C26B | 0.8638 (5) | 1.3512 (4) | 0.91135 (18) | 0.0355 (9) | 0.8469 (14) |
C27B | 1.1846 (5) | 1.2781 (4) | 1.0230 (2) | 0.0449 (11) | 0.8469 (14) |
N1V | 0.929 (2) | 1.5250 (15) | 0.8848 (8) | 0.0425 (9)* | 0.1531 (14) |
C12V | 0.944 (2) | 1.3958 (17) | 0.8834 (8) | 0.0425 (9)* | 0.1531 (14) |
C13V | 1.074 (2) | 1.343 (2) | 0.9104 (8) | 0.0425 (9)* | 0.1531 (14) |
C14V | 1.196 (2) | 1.4242 (17) | 0.9397 (9) | 0.0425 (9)* | 0.1531 (14) |
C15V | 1.177 (2) | 1.5572 (18) | 0.9400 (10) | 0.0425 (9)* | 0.1531 (14) |
C16V | 1.042 (2) | 1.607 (2) | 0.9148 (9) | 0.0425 (9)* | 0.1531 (14) |
C17V | 1.338 (2) | 1.3762 (18) | 0.9718 (10) | 0.0425 (9)* | 0.1531 (14) |
N2V | 1.781 (2) | 1.1136 (19) | 1.0498 (7) | 0.0425 (9)* | 0.1531 (14) |
C22V | 1.663 (2) | 1.1569 (19) | 1.0816 (10) | 0.0425 (9)* | 0.1531 (14) |
C23V | 1.520 (2) | 1.197 (2) | 1.0573 (8) | 0.0425 (9)* | 0.1531 (14) |
C24V | 1.502 (2) | 1.193 (2) | 0.9973 (8) | 0.0425 (9)* | 0.1531 (14) |
C25V | 1.628 (2) | 1.151 (2) | 0.9658 (9) | 0.0425 (9)* | 0.1531 (14) |
C26V | 1.764 (2) | 1.107 (2) | 0.9915 (8) | 0.0425 (9)* | 0.1531 (14) |
C27V | 1.353 (2) | 1.2305 (18) | 0.9658 (10) | 0.0425 (9)* | 0.1531 (14) |
O1C | 0.5413 (3) | 1.4813 (3) | 0.86825 (14) | 0.0362 (7) | 0.8469 (14) |
O2C | 0.3453 (3) | 1.3568 (3) | 0.88713 (13) | 0.0369 (6) | 0.8469 (14) |
O3C | 0.2151 (10) | 1.1182 (5) | 0.6520 (4) | 0.0335 (10) | 0.8469 (14) |
O4C | 0.3843 (11) | 1.2246 (8) | 0.6085 (3) | 0.0447 (12) | 0.8469 (14) |
C1C | 0.3259 (4) | 1.4346 (3) | 0.79467 (15) | 0.0275 (8) | 0.8469 (14) |
C2C | 0.4070 (5) | 1.3468 (3) | 0.74518 (17) | 0.0260 (8) | 0.8469 (14) |
C3C | 0.2767 (6) | 1.3420 (4) | 0.6922 (2) | 0.0290 (8) | 0.8469 (14) |
C4C | 0.1168 (6) | 1.3566 (5) | 0.7176 (3) | 0.0324 (12) | 0.8469 (14) |
C5C | 0.1537 (4) | 1.3816 (4) | 0.78379 (16) | 0.0313 (8) | 0.8469 (14) |
C6C | 0.4024 (4) | 1.4194 (4) | 0.85476 (15) | 0.0282 (8) | 0.8469 (14) |
C7C | 0.3319 (5) | 1.5801 (3) | 0.78932 (17) | 0.0389 (9) | 0.8469 (14) |
C8C | 0.2962 (6) | 1.2231 (5) | 0.64648 (18) | 0.0290 (9) | 0.8469 (14) |
C9C | 0.4371 (5) | 1.2109 (4) | 0.76067 (17) | 0.0319 (8) | 0.8469 (14) |
C10C | 0.5635 (5) | 1.4039 (4) | 0.73215 (18) | 0.0406 (10) | 0.8469 (14) |
O1W | 0.196 (7) | 1.118 (3) | 0.654 (3) | 0.0425 (9)* | 0.1531 (14) |
O2W | 0.372 (7) | 1.212 (5) | 0.6104 (16) | 0.0425 (9)* | 0.1531 (14) |
O3W | 0.6568 (17) | 1.5624 (16) | 0.8241 (7) | 0.0425 (9)* | 0.1531 (14) |
O4W | 0.567 (2) | 1.4222 (18) | 0.8731 (6) | 0.0425 (9)* | 0.1531 (14) |
C1W | 0.281 (3) | 1.3378 (18) | 0.6967 (10) | 0.0425 (9)* | 0.1531 (14) |
C2W | 0.399 (2) | 1.3246 (18) | 0.7507 (9) | 0.0425 (9)* | 0.1531 (14) |
C3W | 0.4018 (19) | 1.4635 (17) | 0.7891 (7) | 0.0425 (9)* | 0.1531 (14) |
C4W | 0.383 (3) | 1.5580 (16) | 0.7446 (7) | 0.0425 (9)* | 0.1531 (14) |
C5W | 0.318 (3) | 1.478 (2) | 0.6850 (7) | 0.0425 (9)* | 0.1531 (14) |
C6W | 0.288 (4) | 1.219 (3) | 0.6502 (10) | 0.0425 (9)* | 0.1531 (14) |
C7W | 0.111 (3) | 1.335 (4) | 0.713 (2) | 0.0425 (9)* | 0.1531 (14) |
C8W | 0.5451 (19) | 1.4811 (16) | 0.8329 (7) | 0.0425 (9)* | 0.1531 (14) |
C9W | 0.563 (2) | 1.298 (2) | 0.7284 (10) | 0.0425 (9)* | 0.1531 (14) |
C10W | 0.361 (3) | 1.212 (2) | 0.7844 (10) | 0.0425 (9)* | 0.1531 (14) |
N1D | 0.3187 (3) | 0.9033 (3) | 0.59041 (11) | 0.0321 (6) | |
N2D | 0.6806 (3) | 0.0958 (3) | 0.40942 (12) | 0.0327 (6) | |
C12D | 0.2625 (4) | 0.7824 (3) | 0.59086 (14) | 0.0344 (8) | |
C13D | 0.3307 (4) | 0.6715 (3) | 0.56397 (14) | 0.0326 (7) | |
C14D | 0.4612 (4) | 0.6815 (3) | 0.53361 (13) | 0.0291 (7) | |
C15D | 0.5197 (4) | 0.8078 (3) | 0.53341 (15) | 0.0332 (7) | |
C16D | 0.4458 (4) | 0.9144 (3) | 0.56219 (15) | 0.0358 (8) | |
C17D | 0.5405 (4) | 0.5657 (3) | 0.50138 (14) | 0.0292 (7) | |
C22D | 0.7398 (4) | 0.2157 (3) | 0.41099 (14) | 0.0329 (7) | |
C23D | 0.6732 (4) | 0.3286 (3) | 0.43886 (14) | 0.0303 (7) | |
C24D | 0.5392 (4) | 0.3172 (3) | 0.46712 (13) | 0.0275 (7) | |
C25D | 0.4779 (4) | 0.1920 (3) | 0.46500 (16) | 0.0359 (8) | |
C26D | 0.5505 (4) | 0.0860 (3) | 0.43646 (15) | 0.0346 (8) | |
C27D | 0.4599 (4) | 0.4327 (3) | 0.49999 (15) | 0.0312 (7) | |
O1E | 0.6154 (5) | −0.2265 (5) | 0.38867 (17) | 0.0404 (11) | 0.8469 (14) |
O2E | 0.7904 (8) | −0.1203 (5) | 0.3475 (2) | 0.0355 (10) | 0.8469 (14) |
O3E | 0.6754 (4) | −0.3583 (3) | 0.10865 (13) | 0.0448 (7) | 0.8469 (14) |
O4E | 0.4770 (4) | −0.4831 (3) | 0.12527 (14) | 0.0465 (8) | 0.8469 (14) |
C1E | 0.7241 (6) | −0.3437 (4) | 0.30411 (19) | 0.0288 (9) | 0.8469 (14) |
C2E | 0.6025 (4) | −0.3391 (4) | 0.24881 (16) | 0.0304 (9) | 0.8469 (14) |
C3E | 0.6812 (5) | −0.4331 (4) | 0.20125 (16) | 0.0345 (9) | 0.8469 (14) |
C4E | 0.8576 (5) | −0.3978 (5) | 0.21409 (17) | 0.0448 (11) | 0.8469 (14) |
C5E | 0.8872 (4) | −0.3474 (4) | 0.28032 (16) | 0.0317 (8) | 0.8469 (14) |
C6E | 0.7046 (6) | −0.2252 (5) | 0.35114 (18) | 0.0290 (9) | 0.8469 (14) |
C7E | 0.6983 (7) | −0.4659 (5) | 0.33044 (18) | 0.0407 (10) | 0.8469 (14) |
C8E | 0.6135 (5) | −0.4193 (4) | 0.14068 (16) | 0.0341 (9) | 0.8469 (14) |
C9E | 0.5957 (5) | −0.2008 (4) | 0.23384 (19) | 0.0375 (9) | 0.8469 (14) |
C10E | 0.4353 (5) | −0.3837 (5) | 0.2574 (2) | 0.0468 (11) | 0.8469 (14) |
O1X | 0.495 (2) | −0.3978 (17) | 0.1216 (6) | 0.0425 (9)* | 0.1531 (14) |
O2X | 0.3787 (17) | −0.5460 (16) | 0.1658 (7) | 0.0425 (9)* | 0.1531 (14) |
O3X | 0.586 (4) | −0.210 (3) | 0.3798 (12) | 0.0425 (9)* | 0.1531 (14) |
O4X | 0.799 (5) | −0.109 (3) | 0.3568 (19) | 0.0425 (9)* | 0.1531 (14) |
C1X | 0.6263 (17) | −0.4489 (17) | 0.2101 (7) | 0.0425 (9)* | 0.1531 (14) |
C2X | 0.630 (2) | −0.3086 (17) | 0.2469 (8) | 0.0425 (9)* | 0.1531 (14) |
C3X | 0.730 (4) | −0.326 (2) | 0.3050 (10) | 0.0425 (9)* | 0.1531 (14) |
C4X | 0.696 (5) | −0.468 (3) | 0.3137 (9) | 0.0425 (9)* | 0.1531 (14) |
C5X | 0.600 (2) | −0.5354 (19) | 0.2567 (8) | 0.0425 (9)* | 0.1531 (14) |
C6X | 0.4950 (19) | −0.4643 (15) | 0.1607 (6) | 0.0425 (9)* | 0.1531 (14) |
C7X | 0.783 (2) | −0.487 (2) | 0.1849 (9) | 0.0425 (9)* | 0.1531 (14) |
C8X | 0.701 (4) | −0.211 (3) | 0.3522 (9) | 0.0425 (9)* | 0.1531 (14) |
C9X | 0.461 (2) | −0.267 (2) | 0.2605 (10) | 0.0425 (9)* | 0.1531 (14) |
C10X | 0.694 (3) | −0.200 (2) | 0.2154 (10) | 0.0425 (9)* | 0.1531 (14) |
N1F | 0.2769 (4) | −0.3893 (3) | 0.05088 (15) | 0.0355 (8) | 0.8469 (14) |
N2F | −0.5810 (4) | 0.0207 (3) | −0.11166 (15) | 0.0349 (7) | 0.8469 (14) |
C12F | 0.1585 (6) | −0.3463 (4) | 0.08117 (19) | 0.0394 (10) | 0.8469 (14) |
C13F | 0.0170 (6) | −0.3071 (5) | 0.0568 (2) | 0.0396 (10) | 0.8469 (14) |
C14F | −0.0052 (5) | −0.3124 (4) | −0.00306 (18) | 0.0333 (8) | 0.8469 (14) |
C15F | 0.1183 (5) | −0.3546 (4) | −0.03497 (18) | 0.0374 (9) | 0.8469 (14) |
C16F | 0.2563 (5) | −0.3928 (4) | −0.00668 (18) | 0.0392 (9) | 0.8469 (14) |
C17F | −0.1585 (5) | −0.2728 (4) | −0.0320 (2) | 0.0400 (10) | 0.8469 (14) |
C22F | −0.5649 (5) | −0.1068 (4) | −0.11249 (19) | 0.0403 (10) | 0.8469 (14) |
C23F | −0.4346 (5) | −0.1605 (4) | −0.08679 (19) | 0.0358 (9) | 0.8469 (14) |
C24F | −0.3124 (4) | −0.0785 (4) | −0.05744 (15) | 0.0281 (7) | 0.8469 (14) |
C25F | −0.3288 (5) | 0.0542 (4) | −0.05718 (18) | 0.0354 (9) | 0.8469 (14) |
C26F | −0.4631 (5) | 0.1000 (4) | −0.08404 (18) | 0.0367 (9) | 0.8469 (14) |
C27F | −0.1671 (4) | −0.1266 (4) | −0.02665 (17) | 0.0299 (8) | 0.8469 (14) |
N1Y | −0.747 (2) | −0.1018 (19) | −0.0586 (7) | 0.0425 (9)* | 0.1531 (14) |
C12Y | −0.628 (2) | −0.1469 (19) | −0.0897 (10) | 0.0425 (9)* | 0.1531 (14) |
C13Y | −0.485 (3) | −0.186 (2) | −0.0656 (8) | 0.0425 (9)* | 0.1531 (14) |
C14Y | −0.460 (2) | −0.179 (2) | −0.0056 (8) | 0.0425 (9)* | 0.1531 (14) |
C15Y | −0.583 (2) | −0.135 (2) | 0.0265 (9) | 0.0425 (9)* | 0.1531 (14) |
C16Y | −0.723 (2) | −0.098 (2) | −0.0006 (8) | 0.0425 (9)* | 0.1531 (14) |
C17Y | −0.305 (2) | −0.2201 (18) | 0.0201 (10) | 0.0425 (9)* | 0.1531 (14) |
N2Y | 0.132 (2) | −0.5057 (16) | 0.0945 (8) | 0.0425 (9)* | 0.1531 (14) |
C22Y | 0.116 (3) | −0.3764 (19) | 0.0952 (10) | 0.0425 (9)* | 0.1531 (14) |
C23Y | −0.019 (2) | −0.327 (3) | 0.0691 (10) | 0.0425 (9)* | 0.1531 (14) |
C24Y | −0.142 (2) | −0.4119 (18) | 0.0415 (10) | 0.0425 (9)* | 0.1531 (14) |
C25Y | −0.122 (2) | −0.5460 (19) | 0.0373 (9) | 0.0425 (9)* | 0.1531 (14) |
C26Y | 0.012 (2) | −0.586 (2) | 0.0676 (9) | 0.0425 (9)* | 0.1531 (14) |
C27Y | −0.292 (2) | −0.3667 (18) | 0.0130 (10) | 0.0425 (9)* | 0.1531 (14) |
O1G | −1.2838 (10) | −0.3774 (5) | −0.3438 (3) | 0.0361 (10) | 0.8469 (14) |
O2G | −1.1414 (9) | −0.2544 (6) | −0.39012 (19) | 0.0412 (9) | 0.8469 (14) |
O3G | −0.8481 (3) | 0.0623 (3) | −0.17325 (13) | 0.0367 (6) | 0.8469 (14) |
O4G | −0.9431 (4) | −0.0806 (4) | −0.12303 (14) | 0.0515 (9) | 0.8469 (14) |
C1G | −1.2334 (4) | −0.1572 (4) | −0.29768 (16) | 0.0261 (9) | 0.8469 (14) |
C2G | −1.1072 (4) | −0.1744 (3) | −0.24584 (16) | 0.0270 (8) | 0.8469 (14) |
C3G | −1.1037 (4) | −0.0367 (4) | −0.20677 (15) | 0.0298 (8) | 0.8469 (14) |
C4G | −1.1229 (5) | 0.0609 (4) | −0.24922 (17) | 0.0371 (9) | 0.8469 (14) |
C5G | −1.1908 (5) | −0.0186 (3) | −0.30878 (16) | 0.0323 (8) | 0.8469 (14) |
C6G | −1.2150 (6) | −0.2653 (4) | −0.34925 (16) | 0.0272 (9) | 0.8469 (14) |
C7G | −1.4028 (5) | −0.1582 (8) | −0.27979 (19) | 0.0342 (11) | 0.8469 (14) |
C8G | −0.9580 (4) | −0.0188 (4) | −0.16335 (17) | 0.0325 (8) | 0.8469 (14) |
C9G | −0.9455 (4) | −0.2002 (4) | −0.26872 (17) | 0.0340 (8) | 0.8469 (14) |
C10G | −1.1471 (5) | −0.2846 (4) | −0.21297 (18) | 0.0390 (9) | 0.8469 (14) |
O1Z | −0.9487 (19) | −0.018 (2) | −0.1306 (9) | 0.0425 (9)* | 0.1531 (14) |
O2Z | −1.146 (2) | −0.1403 (16) | −0.1133 (6) | 0.0425 (9)* | 0.1531 (14) |
O3Z | −1.274 (7) | −0.364 (3) | −0.3489 (19) | 0.0425 (9)* | 0.1531 (14) |
O4Z | −1.132 (6) | −0.245 (4) | −0.3978 (12) | 0.0425 (9)* | 0.1531 (14) |
C1Z | −1.1661 (19) | −0.0602 (17) | −0.2045 (6) | 0.0425 (9)* | 0.1531 (14) |
C2Z | −1.086 (2) | −0.1459 (18) | −0.2546 (8) | 0.0425 (9)* | 0.1531 (14) |
C3Z | −1.214 (3) | −0.139 (3) | −0.3066 (8) | 0.0425 (9)* | 0.1531 (14) |
C4Z | −1.375 (3) | −0.146 (6) | −0.2827 (9) | 0.0425 (9)* | 0.1531 (14) |
C5Z | −1.341 (2) | −0.113 (2) | −0.2155 (8) | 0.0425 (9)* | 0.1531 (14) |
C6Z | −1.0896 (19) | −0.0754 (17) | −0.1454 (6) | 0.0425 (9)* | 0.1531 (14) |
C7Z | −1.167 (3) | 0.0850 (16) | −0.2110 (10) | 0.0425 (9)* | 0.1531 (14) |
C8Z | −1.202 (4) | −0.254 (3) | −0.3554 (7) | 0.0425 (9)* | 0.1531 (14) |
C9Z | −1.051 (3) | −0.2850 (18) | −0.2414 (11) | 0.0425 (9)* | 0.1531 (14) |
C10Z | −0.931 (2) | −0.086 (2) | −0.2713 (10) | 0.0425 (9)* | 0.1531 (14) |
N1H | −1.1782 (3) | −0.5864 (3) | −0.40893 (11) | 0.0310 (6) | |
N2H | −0.8214 (3) | −1.3975 (3) | −0.58706 (12) | 0.0323 (6) | |
C12H | −1.2375 (4) | −0.7066 (3) | −0.41000 (14) | 0.0331 (7) | |
C13H | −1.1707 (4) | −0.8189 (3) | −0.43655 (13) | 0.0296 (7) | |
C14H | −1.0362 (4) | −0.8105 (3) | −0.46476 (13) | 0.0276 (7) | |
C15H | −0.9732 (4) | −0.6848 (3) | −0.46316 (15) | 0.0336 (7) | |
C16H | −1.0465 (4) | −0.5777 (3) | −0.43505 (15) | 0.0347 (7) | |
C17H | −0.9583 (4) | −0.9267 (3) | −0.49657 (14) | 0.0289 (7) | |
C22H | −0.7649 (4) | −1.2772 (3) | −0.58853 (14) | 0.0333 (7) | |
C23H | −0.8326 (4) | −1.1646 (3) | −0.56088 (14) | 0.0325 (7) | |
C24H | −0.9619 (4) | −1.1750 (3) | −0.53023 (13) | 0.0280 (7) | |
C25H | −1.0196 (4) | −1.3012 (3) | −0.52919 (15) | 0.0334 (7) | |
C26H | −0.9476 (4) | −1.4076 (3) | −0.55794 (15) | 0.0350 (8) | |
C27H | −1.0403 (4) | −1.0589 (3) | −0.49781 (14) | 0.0305 (7) | |
H2A | 1.7975 | 0.9602 | 1.1433 | 0.063* | 0.8469 (14) |
H4A | 2.2528 | 1.4595 | 1.3703 | 0.054* | 0.8469 (14) |
H3A | 2.3427 | 1.1768 | 1.2971 | 0.037* | 0.8469 (14) |
H4A1 | 2.2825 | 0.9934 | 1.3290 | 0.049* | 0.8469 (14) |
H4A2 | 2.1170 | 1.0465 | 1.3495 | 0.049* | 0.8469 (14) |
H5A1 | 1.9875 | 0.9510 | 1.2651 | 0.048* | 0.8469 (14) |
H5A2 | 2.1470 | 0.8776 | 1.2500 | 0.048* | 0.8469 (14) |
H7A1 | 2.3629 | 1.0248 | 1.2175 | 0.068* | 0.8469 (14) |
H7A2 | 2.2951 | 1.0767 | 1.1596 | 0.068* | 0.8469 (14) |
H7A3 | 2.2695 | 0.9262 | 1.1648 | 0.068* | 0.8469 (14) |
H9A1 | 1.9130 | 1.1646 | 1.2829 | 0.069* | 0.8469 (14) |
H9A2 | 1.8908 | 1.2334 | 1.2266 | 0.069* | 0.8469 (14) |
H9A3 | 1.9621 | 1.3158 | 1.2879 | 0.069* | 0.8469 (14) |
H10A | 2.2978 | 1.2717 | 1.2075 | 0.070* | 0.8469 (14) |
H10B | 2.1946 | 1.3804 | 1.2423 | 0.070* | 0.8469 (14) |
H10C | 2.1237 | 1.2980 | 1.1809 | 0.070* | 0.8469 (14) |
H2U | 2.2536 | 1.4478 | 1.3731 | 0.064* | 0.15 |
H4U | 1.9195 | 1.0492 | 1.0998 | 0.064* | 0.15 |
H3U | 2.1743 | 0.9802 | 1.2073 | 0.051* | 0.1531 (14) |
H4U1 | 2.3936 | 1.1769 | 1.1887 | 0.051* | 0.1531 (14) |
H4U2 | 2.4315 | 1.0330 | 1.2024 | 0.051* | 0.1531 (14) |
H5U1 | 2.4344 | 1.2590 | 1.2843 | 0.051* | 0.1531 (14) |
H5U2 | 2.4724 | 1.1152 | 1.2979 | 0.051* | 0.1531 (14) |
H7U1 | 2.2346 | 0.9568 | 1.2939 | 0.064* | 0.1531 (14) |
H7U2 | 2.1154 | 1.0200 | 1.3390 | 0.064* | 0.1531 (14) |
H7U3 | 2.3011 | 1.0287 | 1.3579 | 0.064* | 0.1531 (14) |
H9U1 | 2.0428 | 1.3604 | 1.2628 | 0.064* | 0.1531 (14) |
H9U2 | 2.0310 | 1.2969 | 1.1951 | 0.064* | 0.1531 (14) |
H9U3 | 2.1993 | 1.3397 | 1.2300 | 0.064* | 0.1531 (14) |
H10D | 1.8967 | 1.1733 | 1.2882 | 0.064* | 0.1531 (14) |
H10E | 1.9459 | 1.0262 | 1.2663 | 0.064* | 0.1531 (14) |
H10F | 1.8728 | 1.1122 | 1.2202 | 0.064* | 0.1531 (14) |
H12B | 1.6834 | 1.1787 | 1.1189 | 0.049* | 0.8469 (14) |
H13B | 1.4636 | 1.2622 | 1.0750 | 0.046* | 0.8469 (14) |
H15B | 1.2948 | 0.8915 | 1.0202 | 0.040* | 0.8469 (14) |
H16B | 1.5197 | 0.8183 | 1.0662 | 0.043* | 0.8469 (14) |
H17E | 1.1111 | 1.0937 | 1.0309 | 0.043* | 0.8469 (14) |
H17F | 1.1922 | 1.0969 | 0.9723 | 0.043* | 0.8469 (14) |
H22B | 0.6863 | 1.4294 | 1.0234 | 0.045* | 0.8469 (14) |
H23B | 0.9153 | 1.3605 | 1.0688 | 0.044* | 0.8469 (14) |
H25B | 1.0843 | 1.2801 | 0.9111 | 0.042* | 0.8469 (14) |
H26B | 0.8495 | 1.3472 | 0.8703 | 0.043* | 0.8469 (14) |
H27E | 1.2713 | 1.3168 | 1.0055 | 0.054* | 0.8469 (14) |
H27F | 1.1948 | 1.3142 | 1.0652 | 0.054* | 0.8469 (14) |
H12V | 0.8621 | 1.3381 | 0.8629 | 0.051* | 0.1531 (14) |
H13V | 1.0788 | 1.2506 | 0.9088 | 0.051* | 0.1531 (14) |
H15V | 1.2603 | 1.6165 | 0.9582 | 0.051* | 0.1531 (14) |
H16V | 1.0304 | 1.6993 | 0.9188 | 0.051* | 0.1531 (14) |
H17I | 1.3370 | 1.4126 | 1.0138 | 0.051* | 0.1531 (14) |
H17J | 1.4328 | 1.4126 | 0.9585 | 0.051* | 0.1531 (14) |
H22V | 1.6779 | 1.1601 | 1.1226 | 0.051* | 0.1531 (14) |
H23V | 1.4389 | 1.2266 | 1.0809 | 0.051* | 0.1531 (14) |
H25V | 1.6191 | 1.1529 | 0.9251 | 0.051* | 0.1531 (14) |
H26V | 1.8454 | 1.0734 | 0.9686 | 0.051* | 0.1531 (14) |
H27I | 1.2617 | 1.1932 | 0.9813 | 0.051* | 0.1531 (14) |
H27J | 1.3500 | 1.1922 | 0.9239 | 0.051* | 0.1531 (14) |
H1C | 0.5912 | 1.4517 | 0.8957 | 0.054* | 0.8469 (14) |
H3C | 0.2465 | 1.0528 | 0.6302 | 0.050* | 0.8469 (14) |
H3C1 | 0.2947 | 1.4209 | 0.6741 | 0.035* | 0.8469 (14) |
H4C1 | 0.0599 | 1.4308 | 0.7048 | 0.039* | 0.8469 (14) |
H4C2 | 0.0506 | 1.2759 | 0.7047 | 0.039* | 0.8469 (14) |
H5C1 | 0.1426 | 1.2996 | 0.7995 | 0.038* | 0.8469 (14) |
H5C2 | 0.0820 | 1.4466 | 0.8024 | 0.038* | 0.8469 (14) |
H7C1 | 0.2830 | 1.5909 | 0.7508 | 0.058* | 0.8469 (14) |
H7C2 | 0.4418 | 1.6120 | 0.7941 | 0.058* | 0.8469 (14) |
H7C3 | 0.2746 | 1.6304 | 0.8197 | 0.058* | 0.8469 (14) |
H9C1 | 0.3382 | 1.1724 | 0.7692 | 0.048* | 0.8469 (14) |
H9C2 | 0.5143 | 1.2189 | 0.7950 | 0.048* | 0.8469 (14) |
H9C3 | 0.4780 | 1.1546 | 0.7277 | 0.048* | 0.8469 (14) |
H10G | 0.5469 | 1.4907 | 0.7218 | 0.061* | 0.8469 (14) |
H10H | 0.6040 | 1.3462 | 0.6995 | 0.061* | 0.8469 (14) |
H10I | 0.6398 | 1.4115 | 0.7667 | 0.061* | 0.8469 (14) |
H1W | 0.2335 | 1.0520 | 0.6346 | 0.064* | 0.15 |
H3W | 0.7425 | 1.5507 | 0.8432 | 0.064* | 0.15 |
H3W1 | 0.3062 | 1.4697 | 0.8109 | 0.051* | 0.1531 (14) |
H4W1 | 0.3105 | 1.6279 | 0.7575 | 0.051* | 0.1531 (14) |
H4W2 | 0.4869 | 1.5992 | 0.7414 | 0.051* | 0.1531 (14) |
H5W1 | 0.3966 | 1.4759 | 0.6564 | 0.051* | 0.1531 (14) |
H5W2 | 0.2209 | 1.5176 | 0.6697 | 0.051* | 0.1531 (14) |
H7W1 | 0.0956 | 1.4104 | 0.7434 | 0.064* | 0.1531 (14) |
H7W2 | 0.0911 | 1.2540 | 0.7285 | 0.064* | 0.1531 (14) |
H7W3 | 0.0368 | 1.3373 | 0.6788 | 0.064* | 0.1531 (14) |
H9W1 | 0.5611 | 1.2120 | 0.7036 | 0.064* | 0.1531 (14) |
H9W2 | 0.6429 | 1.3012 | 0.7617 | 0.064* | 0.1531 (14) |
H9W3 | 0.5894 | 1.3655 | 0.7057 | 0.064* | 0.1531 (14) |
H10J | 0.2592 | 1.2263 | 0.8000 | 0.064* | 0.1531 (14) |
H10K | 0.4435 | 1.2113 | 0.8167 | 0.064* | 0.1531 (14) |
H10L | 0.3578 | 1.1279 | 0.7578 | 0.064* | 0.1531 (14) |
H12D | 0.1718 | 0.7726 | 0.6105 | 0.041* | |
H13D | 0.2882 | 0.5876 | 0.5662 | 0.039* | |
H15D | 0.6095 | 0.8205 | 0.5137 | 0.040* | |
H16D | 0.4876 | 0.9995 | 0.5618 | 0.043* | |
H17C | 0.6498 | 0.5638 | 0.5197 | 0.035* | |
H17D | 0.5464 | 0.5790 | 0.4607 | 0.035* | |
H22D | 0.8322 | 0.2251 | 0.3922 | 0.039* | |
H23D | 0.7191 | 0.4123 | 0.4385 | 0.036* | |
H25D | 0.3856 | 0.1795 | 0.4833 | 0.043* | |
H26D | 0.5061 | 0.0013 | 0.4359 | 0.041* | |
H27C | 0.4549 | 0.4188 | 0.5406 | 0.037* | |
H27D | 0.3503 | 0.4347 | 0.4820 | 0.037* | |
H2E | 0.7570 | −0.0546 | 0.3685 | 0.053* | 0.8469 (14) |
H4E | 0.4293 | −0.4541 | 0.0972 | 0.070* | 0.8469 (14) |
H3E | 0.6630 | −0.5253 | 0.2069 | 0.041* | 0.8469 (14) |
H4E1 | 0.8870 | −0.3292 | 0.1921 | 0.054* | 0.8469 (14) |
H4E2 | 0.9207 | −0.4757 | 0.2028 | 0.054* | 0.8469 (14) |
H5E1 | 0.9377 | −0.2589 | 0.2880 | 0.038* | 0.8469 (14) |
H5E2 | 0.9569 | −0.4068 | 0.2992 | 0.038* | 0.8469 (14) |
H7E1 | 0.7106 | −0.5439 | 0.3012 | 0.061* | 0.8469 (14) |
H7E2 | 0.5918 | −0.4668 | 0.3429 | 0.061* | 0.8469 (14) |
H7E3 | 0.7758 | −0.4657 | 0.3642 | 0.061* | 0.8469 (14) |
H9E1 | 0.7017 | −0.1709 | 0.2282 | 0.056* | 0.8469 (14) |
H9E2 | 0.5552 | −0.1411 | 0.2658 | 0.056* | 0.8469 (14) |
H9E3 | 0.5259 | −0.2021 | 0.1979 | 0.056* | 0.8469 (14) |
H10M | 0.4376 | −0.4721 | 0.2669 | 0.070* | 0.8469 (14) |
H10N | 0.3662 | −0.3840 | 0.2214 | 0.070* | 0.8469 (14) |
H10O | 0.3954 | −0.3234 | 0.2893 | 0.070* | 0.8469 (14) |
H2X | 0.3001 | −0.5331 | 0.1431 | 0.064* | 0.15 |
H4X | 0.7596 | −0.0412 | 0.3742 | 0.064* | 0.15 |
H3X | 0.8431 | −0.3197 | 0.2980 | 0.051* | 0.1531 (14) |
H4X1 | 0.6351 | −0.4683 | 0.3476 | 0.051* | 0.1531 (14) |
H4X2 | 0.7961 | −0.5130 | 0.3203 | 0.051* | 0.1531 (14) |
H5X1 | 0.4871 | −0.5415 | 0.2624 | 0.051* | 0.1531 (14) |
H5X2 | 0.6379 | −0.6248 | 0.2445 | 0.051* | 0.1531 (14) |
H7X1 | 0.8642 | −0.4915 | 0.2169 | 0.064* | 0.1531 (14) |
H7X2 | 0.8142 | −0.4207 | 0.1626 | 0.064* | 0.1531 (14) |
H7X3 | 0.7690 | −0.5721 | 0.1593 | 0.064* | 0.1531 (14) |
H9X1 | 0.4656 | −0.1797 | 0.2842 | 0.064* | 0.1531 (14) |
H9X2 | 0.4155 | −0.3298 | 0.2818 | 0.064* | 0.1531 (14) |
H9X3 | 0.3947 | −0.2667 | 0.2238 | 0.064* | 0.1531 (14) |
H10P | 0.8024 | −0.2194 | 0.2064 | 0.064* | 0.1531 (14) |
H10Q | 0.6938 | −0.1148 | 0.2409 | 0.064* | 0.1531 (14) |
H10R | 0.6274 | −0.1981 | 0.1791 | 0.064* | 0.1531 (14) |
H12F | 0.1720 | −0.3423 | 0.1222 | 0.047* | 0.8469 (14) |
H13F | −0.0637 | −0.2771 | 0.0807 | 0.047* | 0.8469 (14) |
H15F | 0.1090 | −0.3575 | −0.0760 | 0.045* | 0.8469 (14) |
H16F | 0.3396 | −0.4226 | −0.0293 | 0.047* | 0.8469 (14) |
H17G | −0.1692 | −0.3131 | −0.0737 | 0.048* | 0.8469 (14) |
H17H | −0.2473 | −0.3061 | −0.0137 | 0.048* | 0.8469 (14) |
H22F | −0.6480 | −0.1646 | −0.1319 | 0.048* | 0.8469 (14) |
H23F | −0.4289 | −0.2526 | −0.0892 | 0.043* | 0.8469 (14) |
H25F | −0.2472 | 0.1142 | −0.0384 | 0.043* | 0.8469 (14) |
H26F | −0.4717 | 0.1916 | −0.0828 | 0.044* | 0.8469 (14) |
H27G | −0.0735 | −0.0938 | −0.0423 | 0.036* | 0.8469 (14) |
H27H | −0.1616 | −0.0879 | 0.0152 | 0.036* | 0.8469 (14) |
H12Y | −0.6435 | −0.1526 | −0.1308 | 0.051* | 0.1531 (14) |
H13Y | −0.4055 | −0.2167 | −0.0899 | 0.051* | 0.1531 (14) |
H15Y | −0.5717 | −0.1298 | 0.0676 | 0.051* | 0.1531 (14) |
H16Y | −0.8057 | −0.0697 | 0.0226 | 0.051* | 0.1531 (14) |
H17K | −0.2899 | −0.1825 | 0.0622 | 0.051* | 0.1531 (14) |
H17L | −0.2188 | −0.1842 | 0.0012 | 0.051* | 0.1531 (14) |
H22Y | 0.1992 | −0.3174 | 0.1139 | 0.051* | 0.1531 (14) |
H23Y | −0.0266 | −0.2359 | 0.0701 | 0.051* | 0.1531 (14) |
H25Y | −0.1964 | −0.6074 | 0.0146 | 0.051* | 0.1531 (14) |
H26Y | 0.0188 | −0.6767 | 0.0695 | 0.051* | 0.1531 (14) |
H27K | −0.3819 | −0.4027 | 0.0295 | 0.051* | 0.1531 (14) |
H27L | −0.2999 | −0.4034 | −0.0292 | 0.051* | 0.1531 (14) |
H1G | −1.2548 | −0.4379 | −0.3689 | 0.054* | 0.8469 (14) |
H3G | −0.7681 | 0.0598 | −0.1496 | 0.055* | 0.8469 (14) |
H3G1 | −1.1982 | −0.0316 | −0.1843 | 0.036* | 0.8469 (14) |
H4G1 | −1.0199 | 0.1025 | −0.2527 | 0.044* | 0.8469 (14) |
H4G2 | −1.1957 | 0.1303 | −0.2353 | 0.044* | 0.8469 (14) |
H5G1 | −1.2857 | 0.0230 | −0.3243 | 0.039* | 0.8469 (14) |
H5G2 | −1.1117 | −0.0235 | −0.3373 | 0.039* | 0.8469 (14) |
H7G1 | −1.4118 | −0.0883 | −0.2464 | 0.051* | 0.8469 (14) |
H7G2 | −1.4271 | −0.2429 | −0.2689 | 0.051* | 0.8469 (14) |
H7G3 | −1.4771 | −0.1442 | −0.3126 | 0.051* | 0.8469 (14) |
H9G1 | −0.9178 | −0.1303 | −0.2897 | 0.051* | 0.8469 (14) |
H9G2 | −0.9500 | −0.2844 | −0.2952 | 0.051* | 0.8469 (14) |
H9G3 | −0.8658 | −0.2022 | −0.2359 | 0.051* | 0.8469 (14) |
H10S | −1.2501 | −0.2698 | −0.1981 | 0.058* | 0.8469 (14) |
H10T | −1.0665 | −0.2856 | −0.1803 | 0.058* | 0.8469 (14) |
H10U | −1.1502 | −0.3687 | −0.2395 | 0.058* | 0.8469 (14) |
H1Z | −0.8823 | −0.0455 | −0.1070 | 0.064* | 0.15 |
H3Z | −1.2441 | −0.4338 | −0.3678 | 0.064* | 0.15 |
H3Z1 | −1.2007 | −0.0552 | −0.3213 | 0.051* | 0.1531 (14) |
H4Z1 | −1.4245 | −0.2343 | −0.2947 | 0.051* | 0.1531 (14) |
H4Z2 | −1.4466 | −0.0816 | −0.2973 | 0.051* | 0.1531 (14) |
H5Z1 | −1.3545 | −0.1914 | −0.1977 | 0.051* | 0.1531 (14) |
H5Z2 | −1.4128 | −0.0449 | −0.1989 | 0.051* | 0.1531 (14) |
H7Z1 | −1.2350 | 0.0950 | −0.2461 | 0.064* | 0.1531 (14) |
H7Z2 | −1.0595 | 0.1154 | −0.2144 | 0.064* | 0.1531 (14) |
H7Z3 | −1.2070 | 0.1369 | −0.1767 | 0.064* | 0.1531 (14) |
H9Z1 | −1.0042 | −0.3362 | −0.2744 | 0.064* | 0.1531 (14) |
H9Z2 | −1.1489 | −0.3285 | −0.2353 | 0.064* | 0.1531 (14) |
H9Z3 | −0.9767 | −0.2780 | −0.2062 | 0.064* | 0.1531 (14) |
H10V | −0.9504 | 0.0015 | −0.2799 | 0.064* | 0.1531 (14) |
H10W | −0.8971 | −0.1422 | −0.3058 | 0.064* | 0.1531 (14) |
H10$ | −0.8487 | −0.0814 | −0.2387 | 0.064* | 0.1531 (14) |
H12H | −1.3305 | −0.7154 | −0.3915 | 0.040* | |
H13H | −1.2171 | −0.9021 | −0.4355 | 0.036* | |
H15H | −0.8803 | −0.6731 | −0.4813 | 0.040* | |
H16H | −1.0010 | −0.4932 | −0.4342 | 0.042* | |
H17A | −0.8492 | −0.9293 | −0.4782 | 0.035* | |
H17B | −0.9517 | −0.9139 | −0.5373 | 0.035* | |
H22H | −0.6757 | −1.2682 | −0.6091 | 0.040* | |
H23H | −0.7900 | −1.0807 | −0.5631 | 0.039* | |
H25H | −1.1082 | −1.3134 | −0.5087 | 0.040* | |
H26H | −0.9894 | −1.4925 | −0.5571 | 0.042* | |
H27A | −1.0461 | −1.0722 | −0.4571 | 0.037* | |
H27B | −1.1496 | −1.0563 | −0.5160 | 0.037* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0503 (19) | 0.074 (2) | 0.0350 (16) | −0.0158 (17) | −0.0050 (13) | 0.0179 (16) |
O2A | 0.0360 (16) | 0.0410 (17) | 0.0466 (17) | −0.0030 (13) | −0.0092 (13) | 0.0109 (13) |
O3A | 0.0492 (18) | 0.034 (3) | 0.0410 (16) | −0.008 (2) | 0.0158 (14) | −0.0018 (16) |
O4A | 0.0458 (18) | 0.0249 (17) | 0.037 (2) | −0.0067 (18) | 0.0123 (19) | −0.0024 (16) |
C1A | 0.0274 (19) | 0.0291 (19) | 0.0311 (18) | 0.0006 (14) | 0.0021 (14) | 0.0016 (14) |
C2A | 0.038 (2) | 0.032 (2) | 0.0288 (18) | 0.0030 (17) | 0.0020 (16) | 0.0027 (16) |
C3A | 0.0313 (19) | 0.030 (2) | 0.0304 (18) | 0.0010 (15) | 0.0008 (15) | 0.0049 (15) |
C4A | 0.046 (3) | 0.031 (2) | 0.045 (3) | 0.002 (2) | −0.002 (2) | 0.0076 (18) |
C5A | 0.048 (2) | 0.034 (2) | 0.038 (2) | −0.0067 (17) | −0.0009 (17) | 0.0077 (16) |
C6A | 0.035 (2) | 0.036 (2) | 0.032 (2) | 0.0009 (16) | 0.0091 (16) | 0.0010 (16) |
C7A | 0.040 (2) | 0.052 (2) | 0.043 (2) | 0.0049 (18) | 0.0071 (17) | −0.0001 (18) |
C8A | 0.0308 (19) | 0.027 (2) | 0.0287 (18) | −0.0005 (17) | 0.0021 (15) | 0.0006 (14) |
C9A | 0.039 (2) | 0.053 (3) | 0.044 (2) | 0.0165 (19) | −0.0005 (18) | 0.0003 (19) |
C10A | 0.063 (3) | 0.037 (2) | 0.041 (2) | −0.007 (2) | 0.000 (2) | 0.0133 (18) |
N1B | 0.0322 (17) | 0.0396 (18) | 0.0345 (16) | 0.0007 (13) | −0.0009 (13) | 0.0066 (14) |
C12B | 0.036 (2) | 0.037 (2) | 0.045 (2) | −0.0049 (17) | −0.0069 (18) | 0.0044 (18) |
C13B | 0.035 (2) | 0.031 (2) | 0.049 (2) | −0.0053 (16) | −0.0043 (18) | 0.0118 (18) |
C14B | 0.0281 (18) | 0.039 (2) | 0.0317 (18) | 0.0002 (15) | −0.0015 (14) | 0.0034 (15) |
C15B | 0.0291 (18) | 0.032 (2) | 0.0362 (19) | −0.0016 (14) | 0.0017 (15) | 0.0014 (15) |
C16B | 0.035 (2) | 0.036 (2) | 0.0354 (19) | 0.0024 (16) | 0.0031 (16) | 0.0042 (16) |
C17B | 0.034 (2) | 0.036 (2) | 0.035 (2) | 0.0015 (16) | −0.0019 (16) | 0.0012 (16) |
N2B | 0.0273 (16) | 0.0283 (16) | 0.0368 (17) | −0.0022 (12) | −0.0025 (13) | 0.0042 (13) |
C22B | 0.038 (2) | 0.034 (2) | 0.037 (2) | 0.0012 (17) | 0.0058 (17) | −0.0009 (17) |
C23B | 0.044 (2) | 0.033 (2) | 0.031 (2) | −0.0024 (17) | −0.0047 (17) | 0.0019 (16) |
C24B | 0.034 (2) | 0.0244 (19) | 0.041 (2) | −0.0038 (15) | −0.0074 (17) | 0.0028 (16) |
C25B | 0.030 (2) | 0.036 (2) | 0.040 (2) | 0.0029 (16) | 0.0058 (17) | 0.0075 (17) |
C26B | 0.033 (2) | 0.040 (2) | 0.034 (2) | −0.0019 (17) | 0.0021 (16) | 0.0082 (17) |
C27B | 0.037 (2) | 0.038 (2) | 0.055 (3) | −0.0001 (18) | −0.0170 (19) | 0.0067 (19) |
O1C | 0.0318 (15) | 0.0335 (16) | 0.0423 (17) | −0.0045 (12) | −0.0064 (12) | 0.0095 (13) |
O2C | 0.0322 (15) | 0.0461 (17) | 0.0335 (14) | 0.0005 (12) | 0.0041 (11) | 0.0094 (12) |
O3C | 0.039 (3) | 0.0273 (14) | 0.0329 (16) | −0.0018 (14) | 0.0141 (18) | −0.0033 (11) |
O4C | 0.047 (3) | 0.052 (3) | 0.0345 (16) | −0.0137 (19) | 0.0165 (14) | −0.0015 (17) |
C1C | 0.0302 (19) | 0.0231 (18) | 0.0276 (18) | 0.0013 (14) | −0.0018 (14) | 0.0022 (14) |
C2C | 0.0250 (18) | 0.0244 (19) | 0.0277 (18) | −0.0011 (14) | 0.0067 (14) | 0.0001 (14) |
C3C | 0.032 (2) | 0.0254 (18) | 0.029 (2) | −0.0026 (14) | 0.0013 (15) | 0.0045 (15) |
C4C | 0.033 (2) | 0.032 (3) | 0.030 (2) | 0.0089 (17) | 0.0011 (16) | 0.000 (2) |
C5C | 0.0255 (18) | 0.0354 (19) | 0.0315 (18) | 0.0061 (14) | 0.0023 (14) | 0.0018 (14) |
C6C | 0.0271 (18) | 0.0242 (18) | 0.0325 (18) | 0.0049 (14) | 0.0056 (15) | 0.0011 (15) |
C7C | 0.051 (2) | 0.0238 (17) | 0.039 (2) | 0.0010 (15) | −0.0036 (17) | 0.0028 (14) |
C8C | 0.031 (2) | 0.034 (2) | 0.0219 (18) | 0.0006 (15) | 0.0046 (16) | 0.0028 (15) |
C9C | 0.035 (2) | 0.0273 (19) | 0.0325 (19) | 0.0088 (15) | 0.0041 (16) | 0.0014 (15) |
C10C | 0.034 (2) | 0.051 (3) | 0.035 (2) | −0.0096 (18) | 0.0070 (16) | −0.0001 (18) |
N1D | 0.0350 (15) | 0.0328 (15) | 0.0265 (13) | 0.0030 (11) | 0.0010 (11) | 0.0003 (11) |
N2D | 0.0333 (15) | 0.0304 (15) | 0.0334 (14) | 0.0041 (11) | 0.0055 (11) | 0.0012 (11) |
C12D | 0.0347 (18) | 0.0343 (18) | 0.0321 (16) | 0.0002 (14) | 0.0070 (14) | −0.0020 (13) |
C13D | 0.0345 (17) | 0.0302 (17) | 0.0324 (16) | 0.0015 (13) | 0.0081 (13) | 0.0011 (13) |
C14D | 0.0284 (16) | 0.0303 (17) | 0.0280 (15) | 0.0029 (12) | 0.0003 (12) | 0.0046 (12) |
C15D | 0.0280 (16) | 0.0316 (17) | 0.0392 (18) | 0.0031 (13) | 0.0043 (14) | 0.0035 (14) |
C16D | 0.0361 (18) | 0.0295 (17) | 0.0397 (18) | 0.0001 (14) | 0.0027 (15) | 0.0004 (14) |
C17D | 0.0257 (16) | 0.0290 (16) | 0.0329 (16) | 0.0032 (12) | 0.0040 (12) | 0.0045 (13) |
C22D | 0.0319 (17) | 0.0365 (18) | 0.0320 (16) | 0.0041 (14) | 0.0098 (13) | 0.0067 (13) |
C23D | 0.0291 (16) | 0.0290 (16) | 0.0332 (16) | −0.0001 (12) | 0.0049 (13) | 0.0060 (13) |
C24D | 0.0248 (15) | 0.0305 (16) | 0.0265 (14) | 0.0031 (12) | 0.0010 (12) | 0.0039 (12) |
C25D | 0.0303 (17) | 0.0336 (18) | 0.044 (2) | −0.0002 (13) | 0.0124 (15) | 0.0038 (15) |
C26D | 0.0310 (17) | 0.0297 (17) | 0.0431 (19) | −0.0006 (13) | 0.0071 (14) | 0.0049 (14) |
C27D | 0.0308 (17) | 0.0284 (16) | 0.0359 (16) | 0.0030 (12) | 0.0111 (13) | 0.0053 (13) |
O1E | 0.051 (3) | 0.037 (2) | 0.035 (2) | 0.0023 (16) | 0.0189 (19) | 0.0027 (14) |
O2E | 0.0385 (18) | 0.0311 (17) | 0.034 (3) | −0.0034 (13) | 0.0117 (19) | −0.0064 (13) |
O3E | 0.0419 (17) | 0.063 (2) | 0.0305 (14) | 0.0059 (15) | 0.0051 (12) | 0.0104 (14) |
O4E | 0.052 (2) | 0.0408 (18) | 0.0417 (18) | 0.0010 (14) | −0.0137 (14) | 0.0027 (14) |
C1E | 0.0263 (18) | 0.031 (2) | 0.0276 (18) | 0.0013 (16) | 0.0008 (14) | 0.0000 (16) |
C2E | 0.028 (2) | 0.036 (2) | 0.0248 (18) | 0.0054 (16) | −0.0014 (15) | 0.0010 (16) |
C3E | 0.038 (2) | 0.032 (2) | 0.032 (2) | 0.0087 (17) | −0.0016 (17) | 0.0015 (16) |
C4E | 0.036 (2) | 0.067 (3) | 0.031 (2) | 0.016 (2) | 0.0048 (16) | 0.0034 (19) |
C5E | 0.028 (2) | 0.032 (2) | 0.033 (2) | 0.0005 (15) | 0.0020 (15) | 0.0007 (16) |
C6E | 0.0263 (18) | 0.031 (2) | 0.0297 (18) | −0.0001 (15) | 0.0032 (15) | 0.0044 (15) |
C7E | 0.043 (2) | 0.038 (2) | 0.041 (2) | −0.0067 (16) | 0.000 (2) | 0.010 (2) |
C8E | 0.035 (2) | 0.033 (2) | 0.033 (2) | 0.0068 (16) | 0.0004 (17) | 0.0029 (16) |
C9E | 0.041 (2) | 0.034 (2) | 0.039 (2) | 0.0107 (17) | 0.0035 (17) | 0.0071 (17) |
C10E | 0.031 (2) | 0.068 (3) | 0.042 (2) | −0.007 (2) | 0.0027 (17) | 0.014 (2) |
N1F | 0.0371 (19) | 0.0297 (18) | 0.0368 (18) | −0.0011 (14) | −0.0016 (14) | 0.0008 (14) |
N2F | 0.0363 (17) | 0.0293 (17) | 0.0371 (17) | −0.0001 (13) | −0.0019 (13) | 0.0033 (13) |
C12F | 0.045 (3) | 0.040 (2) | 0.033 (2) | −0.0022 (19) | −0.0004 (18) | 0.0080 (17) |
C13F | 0.039 (2) | 0.039 (2) | 0.041 (2) | 0.0001 (18) | 0.0061 (18) | 0.0056 (18) |
C14F | 0.031 (2) | 0.0249 (19) | 0.042 (2) | −0.0033 (15) | −0.0053 (16) | 0.0059 (16) |
C15F | 0.044 (2) | 0.036 (2) | 0.030 (2) | 0.0034 (17) | −0.0005 (17) | 0.0004 (16) |
C16F | 0.036 (2) | 0.041 (2) | 0.037 (2) | 0.0042 (17) | 0.0011 (17) | −0.0018 (17) |
C17F | 0.035 (2) | 0.030 (2) | 0.050 (2) | 0.0013 (16) | −0.0063 (18) | 0.0027 (18) |
C22F | 0.039 (2) | 0.033 (2) | 0.043 (2) | −0.0019 (16) | −0.0085 (18) | −0.0040 (17) |
C23F | 0.035 (2) | 0.0264 (19) | 0.043 (2) | −0.0019 (15) | −0.0016 (17) | 0.0005 (16) |
C24F | 0.0282 (18) | 0.0286 (18) | 0.0277 (17) | −0.0036 (14) | 0.0039 (14) | 0.0055 (14) |
C25F | 0.031 (2) | 0.0289 (19) | 0.045 (2) | −0.0065 (15) | −0.0032 (16) | 0.0053 (16) |
C26F | 0.034 (2) | 0.0282 (19) | 0.047 (2) | −0.0047 (15) | −0.0053 (16) | 0.0091 (16) |
C27F | 0.0264 (18) | 0.0304 (19) | 0.0331 (18) | −0.0017 (14) | −0.0003 (14) | 0.0081 (14) |
O1G | 0.047 (2) | 0.0235 (17) | 0.038 (2) | −0.0042 (15) | 0.0181 (15) | −0.0015 (15) |
O2G | 0.051 (2) | 0.049 (2) | 0.0242 (17) | −0.0135 (15) | 0.0114 (16) | 0.0066 (15) |
O3G | 0.0317 (15) | 0.0350 (15) | 0.0420 (15) | −0.0081 (12) | −0.0052 (12) | 0.0083 (12) |
O4G | 0.0456 (18) | 0.075 (3) | 0.0352 (16) | −0.0170 (17) | −0.0008 (13) | 0.0183 (16) |
C1G | 0.028 (2) | 0.0202 (18) | 0.0292 (18) | −0.0038 (14) | 0.0011 (15) | 0.0032 (14) |
C2G | 0.0258 (19) | 0.0265 (19) | 0.0282 (18) | −0.0010 (14) | 0.0043 (14) | 0.0024 (14) |
C3G | 0.0299 (19) | 0.0279 (19) | 0.0293 (18) | −0.0019 (15) | 0.0029 (15) | −0.0020 (14) |
C4G | 0.039 (2) | 0.0263 (18) | 0.043 (2) | −0.0005 (15) | −0.0094 (17) | 0.0025 (15) |
C5G | 0.035 (2) | 0.0265 (19) | 0.0370 (19) | 0.0013 (15) | 0.0028 (16) | 0.0102 (15) |
C6G | 0.0282 (19) | 0.027 (2) | 0.0271 (18) | −0.0038 (15) | −0.0008 (14) | 0.0088 (14) |
C7G | 0.025 (2) | 0.040 (3) | 0.0367 (19) | 0.005 (2) | 0.0058 (15) | −0.0005 (16) |
C8G | 0.0293 (19) | 0.038 (2) | 0.0282 (19) | −0.0066 (15) | 0.0021 (15) | 0.0014 (16) |
C9G | 0.032 (2) | 0.034 (2) | 0.0341 (19) | 0.0066 (15) | 0.0017 (15) | 0.0011 (15) |
C10G | 0.044 (2) | 0.037 (2) | 0.038 (2) | −0.0052 (17) | 0.0004 (17) | 0.0145 (17) |
N1H | 0.0333 (15) | 0.0308 (15) | 0.0276 (13) | 0.0013 (11) | 0.0027 (11) | 0.0015 (11) |
N2H | 0.0321 (15) | 0.0306 (15) | 0.0318 (14) | 0.0015 (11) | 0.0005 (11) | −0.0002 (11) |
C12H | 0.0357 (18) | 0.0318 (18) | 0.0321 (16) | −0.0003 (13) | 0.0078 (13) | 0.0034 (13) |
C13H | 0.0332 (17) | 0.0263 (16) | 0.0303 (15) | −0.0007 (13) | 0.0059 (13) | 0.0062 (12) |
C14H | 0.0273 (16) | 0.0284 (16) | 0.0279 (15) | 0.0022 (12) | 0.0013 (12) | 0.0074 (12) |
C15H | 0.0261 (16) | 0.0279 (17) | 0.0478 (19) | −0.0016 (12) | 0.0091 (14) | 0.0069 (14) |
C16H | 0.0310 (17) | 0.0289 (17) | 0.0424 (18) | −0.0034 (13) | 0.0019 (14) | 0.0024 (13) |
C17H | 0.0256 (16) | 0.0275 (16) | 0.0333 (16) | 0.0011 (12) | 0.0035 (12) | 0.0042 (13) |
C22H | 0.0326 (17) | 0.0363 (18) | 0.0309 (16) | 0.0021 (14) | 0.0060 (13) | 0.0036 (13) |
C23H | 0.0358 (18) | 0.0290 (17) | 0.0321 (16) | −0.0025 (13) | 0.0058 (14) | 0.0030 (13) |
C24H | 0.0271 (16) | 0.0287 (16) | 0.0273 (14) | −0.0012 (12) | −0.0014 (12) | 0.0046 (12) |
C25H | 0.0273 (16) | 0.0318 (17) | 0.0409 (18) | −0.0009 (13) | 0.0048 (13) | 0.0048 (13) |
C26H | 0.0370 (18) | 0.0262 (17) | 0.0413 (18) | −0.0011 (13) | 0.0026 (14) | 0.0050 (13) |
C27H | 0.0297 (16) | 0.0293 (16) | 0.0335 (16) | 0.0025 (12) | 0.0066 (13) | 0.0058 (13) |
Geometric parameters (Å, º) top
O1A—C6A | 1.219 (5) | O1E—C6E | 1.217 (5) |
O1A—H4U | 0.84 | O2E—C6E | 1.323 (5) |
O2A—C6A | 1.323 (5) | O2E—H2E | 0.84 |
O2A—H2A | 0.84 | O3E—C8E | 1.212 (5) |
O3A—C8A | 1.210 (5) | O4E—C8E | 1.320 (5) |
O4A—C8A | 1.330 (5) | O4E—H4E | 0.84 |
O4A—H4A | 0.84 | C1E—C7E | 1.523 (5) |
C1A—C6A | 1.515 (5) | C1E—C6E | 1.526 (4) |
C1A—C7A | 1.539 (5) | C1E—C5E | 1.546 (6) |
C1A—C5A | 1.549 (5) | C1E—C2E | 1.586 (5) |
C1A—C2A | 1.567 (5) | C2E—C9E | 1.535 (5) |
C2A—C10A | 1.530 (5) | C2E—C10E | 1.535 (5) |
C2A—C9A | 1.537 (5) | C2E—C3E | 1.559 (5) |
C2A—C3A | 1.568 (5) | C3E—C8E | 1.509 (5) |
C3A—C8A | 1.512 (4) | C3E—C4E | 1.533 (5) |
C3A—C4A | 1.541 (5) | C3E—H3E | 1.00 |
C3A—H3A | 1.00 | C4E—C5E | 1.543 (5) |
C4A—C5A | 1.537 (6) | C4E—H4E1 | 0.99 |
C4A—H4A1 | 0.99 | C4E—H4E2 | 0.99 |
C4A—H4A2 | 0.99 | C5E—H5E1 | 0.99 |
C5A—H5A1 | 0.99 | C5E—H5E2 | 0.99 |
C5A—H5A2 | 0.99 | C7E—H7E1 | 0.98 |
C7A—H7A1 | 0.98 | C7E—H7E2 | 0.98 |
C7A—H7A2 | 0.98 | C7E—H7E3 | 0.98 |
C7A—H7A3 | 0.98 | C9E—H9E1 | 0.98 |
C9A—H9A1 | 0.98 | C9E—H9E2 | 0.98 |
C9A—H9A2 | 0.98 | C9E—H9E3 | 0.98 |
C9A—H9A3 | 0.98 | C10E—H10M | 0.98 |
C10A—H10A | 0.98 | C10E—H10N | 0.98 |
C10A—H10B | 0.98 | C10E—H10O | 0.98 |
C10A—H10C | 0.98 | O1X—C6X | 1.235 (9) |
O1U—C6U | 1.218 (11) | O2X—C6X | 1.323 (9) |
O2U—C6U | 1.319 (11) | O2X—H2X | 0.84 |
O2U—H2U | 0.84 | O3X—C8X | 1.227 (10) |
O3U—C8U | 1.222 (9) | O4X—C8X | 1.322 (11) |
O4U—C8U | 1.330 (10) | O4X—H4X | 0.84 |
O4U—H4U | 0.84 | C1X—C6X | 1.517 (9) |
C1U—C6U | 1.493 (10) | C1X—C7X | 1.537 (10) |
C1U—C7U | 1.536 (10) | C1X—C5X | 1.557 (10) |
C1U—C2U | 1.559 (10) | C1X—C2X | 1.558 (10) |
C1U—C5U | 1.563 (10) | C2X—C9X | 1.559 (10) |
C2U—C9U | 1.553 (10) | C2X—C10X | 1.566 (10) |
C2U—C3U | 1.558 (10) | C2X—C3X | 1.572 (11) |
C2U—C10U | 1.562 (10) | C3X—C8X | 1.520 (10) |
C3U—C8U | 1.501 (9) | C3X—C4X | 1.546 (10) |
C3U—C4U | 1.546 (10) | C3X—H3X | 1.00 |
C3U—H3U | 1.00 | C4X—C5X | 1.548 (10) |
C4U—C5U | 1.546 (10) | C4X—H4X1 | 0.99 |
C4U—H4U1 | 0.99 | C4X—H4X2 | 0.99 |
C4U—H4U2 | 0.99 | C5X—H5X1 | 0.99 |
C5U—H5U1 | 0.99 | C5X—H5X2 | 0.99 |
C5U—H5U2 | 0.99 | C7X—H7X1 | 0.98 |
C7U—H7U1 | 0.98 | C7X—H7X2 | 0.98 |
C7U—H7U2 | 0.98 | C7X—H7X3 | 0.98 |
C7U—H7U3 | 0.98 | C9X—H9X1 | 0.98 |
C9U—H9U1 | 0.98 | C9X—H9X2 | 0.98 |
C9U—H9U2 | 0.98 | C9X—H9X3 | 0.98 |
C9U—H9U3 | 0.98 | C10X—H10P | 0.98 |
C10U—H10D | 0.98 | C10X—H10Q | 0.98 |
C10U—H10E | 0.98 | C10X—H10R | 0.98 |
C10U—H10F | 0.98 | N1F—C12F | 1.328 (5) |
N1B—C12B | 1.337 (5) | N1F—C16F | 1.335 (5) |
N1B—C16B | 1.341 (5) | N2F—C22F | 1.329 (5) |
C12B—C13B | 1.378 (6) | N2F—C26F | 1.333 (5) |
C12B—H12B | 0.95 | C12F—C13F | 1.381 (6) |
C13B—C14B | 1.393 (6) | C12F—H12F | 0.95 |
C13B—H13B | 0.95 | C13F—C14F | 1.387 (6) |
C14B—C15B | 1.390 (6) | C13F—H13F | 0.95 |
C14B—C17B | 1.504 (5) | C14F—C15F | 1.383 (6) |
C15B—C16B | 1.384 (5) | C14F—C17F | 1.509 (6) |
C15B—H15B | 0.95 | C15F—C16F | 1.391 (6) |
C16B—H16B | 0.95 | C15F—H15F | 0.95 |
C17B—C27B | 1.509 (6) | C16F—H16F | 0.95 |
C17B—H17E | 0.99 | C17F—C27F | 1.505 (5) |
C17B—H17F | 0.99 | C17F—H17G | 0.99 |
N2B—C22B | 1.337 (5) | C17F—H17H | 0.99 |
N2B—C26B | 1.349 (5) | C22F—C23F | 1.383 (6) |
C22B—C23B | 1.386 (6) | C22F—H22F | 0.95 |
C22B—H22B | 0.95 | C23F—C24F | 1.386 (5) |
C23B—C24B | 1.386 (6) | C23F—H23F | 0.95 |
C23B—H23B | 0.95 | C24F—C25F | 1.385 (5) |
C24B—C25B | 1.394 (6) | C24F—C27F | 1.508 (5) |
C24B—C27B | 1.511 (6) | C25F—C26F | 1.383 (6) |
C25B—C26B | 1.377 (6) | C25F—H25F | 0.95 |
C25B—H25B | 0.95 | C26F—H26F | 0.95 |
C26B—H26B | 0.95 | C27F—H27G | 0.99 |
C27B—H27E | 0.99 | C27F—H27H | 0.99 |
C27B—H27F | 0.99 | N1Y—C12Y | 1.344 (10) |
N1V—C16V | 1.341 (10) | N1Y—C16Y | 1.346 (10) |
N1V—C12V | 1.344 (10) | C12Y—C13Y | 1.391 (10) |
C12V—C13V | 1.392 (10) | C12Y—H12Y | 0.95 |
C12V—H12V | 0.95 | C13Y—C14Y | 1.389 (10) |
C13V—C14V | 1.383 (10) | C13Y—H13Y | 0.95 |
C13V—H13V | 0.95 | C14Y—C15Y | 1.391 (10) |
C14V—C15V | 1.391 (10) | C14Y—C17Y | 1.499 (10) |
C14V—C17V | 1.497 (10) | C15Y—C16Y | 1.386 (10) |
C15V—C16V | 1.392 (10) | C15Y—H15Y | 0.95 |
C15V—H15V | 0.95 | C16Y—H16Y | 0.95 |
C16V—H16V | 0.95 | C17Y—C27Y | 1.508 (10) |
C17V—C27V | 1.503 (10) | C17Y—H17K | 0.99 |
C17V—H17I | 0.99 | C17Y—H17L | 0.99 |
C17V—H17J | 0.99 | N2Y—C22Y | 1.348 (10) |
N2V—C22V | 1.345 (10) | N2Y—C26Y | 1.348 (10) |
N2V—C26V | 1.347 (10) | C22Y—C23Y | 1.395 (10) |
C22V—C23V | 1.396 (10) | C22Y—H22Y | 0.95 |
C22V—H22V | 0.95 | C23Y—C24Y | 1.392 (10) |
C23V—C24V | 1.390 (10) | C23Y—H23Y | 0.95 |
C23V—H23V | 0.95 | C24Y—C25Y | 1.391 (10) |
C24V—C25V | 1.391 (10) | C24Y—C27Y | 1.506 (10) |
C24V—C27V | 1.499 (10) | C25Y—C26Y | 1.390 (10) |
C25V—C26V | 1.380 (10) | C25Y—H25Y | 0.95 |
C25V—H25V | 0.95 | C26Y—H26Y | 0.95 |
C26V—H26V | 0.95 | C27Y—H27K | 0.99 |
C27V—H27I | 0.99 | C27Y—H27L | 0.99 |
C27V—H27J | 0.99 | O1G—C6G | 1.327 (5) |
O1C—C6C | 1.325 (5) | O1G—H1G | 0.84 |
O1C—H1C | 0.84 | O2G—C6G | 1.212 (5) |
O2C—C6C | 1.209 (5) | O3G—C8G | 1.314 (5) |
O3C—C8C | 1.314 (5) | O3G—H3G | 0.84 |
O3C—H3C | 0.84 | O4G—C8G | 1.226 (5) |
O4C—C8C | 1.218 (5) | C1G—C6G | 1.522 (4) |
C1C—C6C | 1.526 (4) | C1G—C7G | 1.543 (5) |
C1C—C7C | 1.538 (4) | C1G—C5G | 1.548 (5) |
C1C—C5C | 1.544 (5) | C1G—C2G | 1.579 (5) |
C1C—C2C | 1.568 (4) | C2G—C10G | 1.534 (5) |
C2C—C10C | 1.532 (5) | C2G—C9G | 1.537 (4) |
C2C—C9C | 1.534 (5) | C2G—C3G | 1.557 (4) |
C2C—C3C | 1.577 (5) | C3G—C8G | 1.517 (5) |
C3C—C8C | 1.511 (5) | C3G—C4G | 1.535 (5) |
C3C—C4C | 1.539 (5) | C3G—H3G1 | 1.00 |
C3C—H3C1 | 1.00 | C4G—C5G | 1.549 (5) |
C4C—C5C | 1.526 (6) | C4G—H4G1 | 0.99 |
C4C—H4C1 | 0.99 | C4G—H4G2 | 0.99 |
C4C—H4C2 | 0.99 | C5G—H5G1 | 0.99 |
C5C—H5C1 | 0.99 | C5G—H5G2 | 0.99 |
C5C—H5C2 | 0.99 | C7G—H7G1 | 0.98 |
C7C—H7C1 | 0.98 | C7G—H7G2 | 0.98 |
C7C—H7C2 | 0.98 | C7G—H7G3 | 0.98 |
C7C—H7C3 | 0.98 | C9G—H9G1 | 0.98 |
C9C—H9C1 | 0.98 | C9G—H9G2 | 0.98 |
C9C—H9C2 | 0.98 | C9G—H9G3 | 0.98 |
C9C—H9C3 | 0.98 | C10G—H10S | 0.98 |
C10C—H10G | 0.98 | C10G—H10T | 0.98 |
C10C—H10H | 0.98 | C10G—H10U | 0.98 |
C10C—H10I | 0.98 | O1Z—C6Z | 1.323 (10) |
O1W—C6W | 1.323 (11) | O1Z—H1Z | 0.84 |
O1W—H1W | 0.84 | O2Z—C6Z | 1.217 (9) |
O2W—C6W | 1.221 (11) | O3Z—C8Z | 1.324 (10) |
O3W—C8W | 1.318 (10) | O3Z—H3Z | 0.84 |
O3W—H3W | 0.84 | O4Z—C8Z | 1.223 (10) |
O4W—C8W | 1.208 (9) | C1Z—C6Z | 1.505 (9) |
C1W—C6W | 1.505 (10) | C1Z—C7Z | 1.540 (10) |
C1W—C7W | 1.543 (10) | C1Z—C2Z | 1.563 (10) |
C1W—C5W | 1.562 (10) | C1Z—C5Z | 1.565 (10) |
C1W—C2W | 1.566 (10) | C2Z—C9Z | 1.554 (10) |
C2W—C9W | 1.551 (10) | C2Z—C10Z | 1.561 (10) |
C2W—C3W | 1.562 (10) | C2Z—C3Z | 1.565 (10) |
C2W—C10W | 1.563 (10) | C3Z—C8Z | 1.515 (10) |
C3W—C8W | 1.507 (9) | C3Z—C4Z | 1.539 (10) |
C3W—C4W | 1.545 (10) | C3Z—H3Z1 | 1.00 |
C3W—H3W1 | 1.00 | C4Z—C5Z | 1.550 (10) |
C4W—C5W | 1.543 (10) | C4Z—H4Z1 | 0.99 |
C4W—H4W1 | 0.99 | C4Z—H4Z2 | 0.99 |
C4W—H4W2 | 0.99 | C5Z—H5Z1 | 0.99 |
C5W—H5W1 | 0.99 | C5Z—H5Z2 | 0.99 |
C5W—H5W2 | 0.99 | C7Z—H7Z1 | 0.98 |
C7W—H7W1 | 0.98 | C7Z—H7Z2 | 0.98 |
C7W—H7W2 | 0.98 | C7Z—H7Z3 | 0.98 |
C7W—H7W3 | 0.98 | C9Z—H9Z1 | 0.98 |
C9W—H9W1 | 0.98 | C9Z—H9Z2 | 0.98 |
C9W—H9W2 | 0.98 | C9Z—H9Z3 | 0.98 |
C9W—H9W3 | 0.98 | C10Z—H10V | 0.98 |
C10W—H10J | 0.98 | C10Z—H10W | 0.98 |
C10W—H10K | 0.98 | C10Z—H10$ | 0.98 |
C10W—H10L | 0.98 | N1H—C12H | 1.335 (4) |
N1D—C16D | 1.336 (5) | N1H—C16H | 1.338 (4) |
N1D—C12D | 1.339 (4) | N2H—C22H | 1.339 (4) |
N2D—C22D | 1.330 (4) | N2H—C26H | 1.340 (4) |
N2D—C26D | 1.340 (4) | C12H—C13H | 1.381 (4) |
C12D—C13D | 1.379 (4) | C12H—H12H | 0.95 |
C12D—H12D | 0.95 | C13H—C14H | 1.386 (4) |
C13D—C14D | 1.388 (4) | C13H—H13H | 0.95 |
C13D—H13D | 0.95 | C14H—C15H | 1.397 (4) |
C14D—C15D | 1.397 (5) | C14H—C17H | 1.503 (4) |
C14D—C17D | 1.510 (4) | C15H—C16H | 1.381 (5) |
C15D—C16D | 1.386 (5) | C15H—H15H | 0.95 |
C15D—H15D | 0.95 | C16H—H16H | 0.95 |
C16D—H16D | 0.95 | C17H—C27H | 1.526 (3) |
C17D—C27D | 1.528 (4) | C17H—H17A | 0.99 |
C17D—H17C | 0.99 | C17H—H17B | 0.99 |
C17D—H17D | 0.99 | C22H—C23H | 1.396 (5) |
C22D—C23D | 1.396 (4) | C22H—H22H | 0.95 |
C22D—H22D | 0.95 | C23H—C24H | 1.384 (4) |
C23D—C24D | 1.387 (4) | C23H—H23H | 0.95 |
C23D—H23D | 0.95 | C24H—C25H | 1.398 (5) |
C24D—C25D | 1.385 (5) | C24H—C27H | 1.510 (4) |
C24D—C27D | 1.514 (4) | C25H—C26H | 1.376 (5) |
C25D—C26D | 1.373 (5) | C25H—H25H | 0.95 |
C25D—H25D | 0.95 | C26H—H26H | 0.95 |
C26D—H26D | 0.95 | C27H—H27A | 0.99 |
C27D—H27C | 0.99 | C27H—H27B | 0.99 |
C27D—H27D | 0.99 | | |
| | | |
C6A—C1A—C7A | 107.3 (3) | C7E—C1E—C6E | 107.6 (4) |
C6A—C1A—C5A | 115.8 (3) | C7E—C1E—C5E | 109.5 (4) |
C7A—C1A—C5A | 109.4 (3) | C6E—C1E—C5E | 113.6 (3) |
C6A—C1A—C2A | 110.0 (3) | C7E—C1E—C2E | 111.8 (3) |
C7A—C1A—C2A | 111.8 (3) | C6E—C1E—C2E | 109.9 (3) |
C5A—C1A—C2A | 102.6 (3) | C5E—C1E—C2E | 104.5 (3) |
C10A—C2A—C9A | 108.5 (4) | C9E—C2E—C10E | 108.5 (3) |
C10A—C2A—C1A | 114.1 (3) | C9E—C2E—C3E | 110.4 (3) |
C9A—C2A—C1A | 109.9 (3) | C10E—C2E—C3E | 113.7 (3) |
C10A—C2A—C3A | 112.7 (4) | C9E—C2E—C1E | 111.2 (3) |
C9A—C2A—C3A | 110.3 (3) | C10E—C2E—C1E | 112.5 (3) |
C1A—C2A—C3A | 101.2 (3) | C3E—C2E—C1E | 100.5 (3) |
C8A—C3A—C4A | 114.5 (4) | C8E—C3E—C4E | 114.0 (3) |
C8A—C3A—C2A | 111.0 (3) | C8E—C3E—C2E | 111.5 (3) |
C4A—C3A—C2A | 105.7 (3) | C4E—C3E—C2E | 104.5 (3) |
C8A—C3A—H3A | 108.5 | C8E—C3E—H3E | 108.9 |
C4A—C3A—H3A | 108.5 | C4E—C3E—H3E | 108.9 |
C2A—C3A—H3A | 108.5 | C2E—C3E—H3E | 108.9 |
C5A—C4A—C3A | 106.1 (4) | C3E—C4E—C5E | 106.5 (3) |
C5A—C4A—H4A1 | 110.5 | C3E—C4E—H4E1 | 110.4 |
C3A—C4A—H4A1 | 110.5 | C5E—C4E—H4E1 | 110.4 |
C5A—C4A—H4A2 | 110.5 | C3E—C4E—H4E2 | 110.4 |
C3A—C4A—H4A2 | 110.5 | C5E—C4E—H4E2 | 110.4 |
H4A1—C4A—H4A2 | 108.7 | H4E1—C4E—H4E2 | 108.6 |
C4A—C5A—C1A | 106.7 (3) | C4E—C5E—C1E | 106.4 (3) |
C4A—C5A—H5A1 | 110.4 | C4E—C5E—H5E1 | 110.5 |
C1A—C5A—H5A1 | 110.4 | C1E—C5E—H5E1 | 110.5 |
C4A—C5A—H5A2 | 110.4 | C4E—C5E—H5E2 | 110.5 |
C1A—C5A—H5A2 | 110.4 | C1E—C5E—H5E2 | 110.5 |
H5A1—C5A—H5A2 | 108.6 | H5E1—C5E—H5E2 | 108.6 |
O1A—C6A—O2A | 122.1 (4) | O1E—C6E—O2E | 122.6 (4) |
O1A—C6A—C1A | 123.1 (4) | O1E—C6E—C1E | 122.6 (4) |
O2A—C6A—C1A | 114.7 (3) | O2E—C6E—C1E | 114.9 (3) |
C1A—C7A—H7A1 | 109.5 | C1E—C7E—H7E1 | 109.5 |
C1A—C7A—H7A2 | 109.5 | C1E—C7E—H7E2 | 109.5 |
H7A1—C7A—H7A2 | 109.5 | H7E1—C7E—H7E2 | 109.5 |
C1A—C7A—H7A3 | 109.5 | C1E—C7E—H7E3 | 109.5 |
H7A1—C7A—H7A3 | 109.5 | H7E1—C7E—H7E3 | 109.5 |
H7A2—C7A—H7A3 | 109.5 | H7E2—C7E—H7E3 | 109.5 |
O3A—C8A—O4A | 123.4 (4) | O3E—C8E—O4E | 122.5 (4) |
O3A—C8A—C3A | 125.4 (4) | O3E—C8E—C3E | 125.1 (4) |
O4A—C8A—C3A | 111.2 (3) | O4E—C8E—C3E | 112.3 (4) |
C2A—C9A—H9A1 | 109.5 | C2E—C9E—H9E1 | 109.5 |
C2A—C9A—H9A2 | 109.5 | C2E—C9E—H9E2 | 109.5 |
H9A1—C9A—H9A2 | 109.5 | H9E1—C9E—H9E2 | 109.5 |
C2A—C9A—H9A3 | 109.5 | C2E—C9E—H9E3 | 109.5 |
H9A1—C9A—H9A3 | 109.5 | H9E1—C9E—H9E3 | 109.5 |
H9A2—C9A—H9A3 | 109.5 | H9E2—C9E—H9E3 | 109.5 |
C2A—C10A—H10A | 109.5 | C2E—C10E—H10M | 109.5 |
C2A—C10A—H10B | 109.5 | C2E—C10E—H10N | 109.5 |
H10A—C10A—H10B | 109.5 | H10M—C10E—H10N | 109.5 |
C2A—C10A—H10C | 109.5 | C2E—C10E—H10O | 109.5 |
H10A—C10A—H10C | 109.5 | H10M—C10E—H10O | 109.5 |
H10B—C10A—H10C | 109.5 | H10N—C10E—H10O | 109.5 |
C6U—O2U—H2U | 120.1 | C6X—O2X—H2X | 108.9 |
C8U—O4U—H4U | 118.4 | C8X—O4X—H4X | 110.7 |
C6U—C1U—C7U | 107 (2) | C6X—C1X—C7X | 109.1 (13) |
C6U—C1U—C2U | 111.9 (12) | C6X—C1X—C5X | 113.4 (11) |
C7U—C1U—C2U | 112.2 (14) | C7X—C1X—C5X | 108.0 (11) |
C6U—C1U—C5U | 113.7 (17) | C6X—C1X—C2X | 110.7 (10) |
C7U—C1U—C5U | 108.0 (13) | C7X—C1X—C2X | 113.8 (11) |
C2U—C1U—C5U | 104.0 (13) | C5X—C1X—C2X | 101.8 (12) |
C9U—C2U—C3U | 109.9 (16) | C1X—C2X—C9X | 110.6 (15) |
C9U—C2U—C1U | 113.8 (17) | C1X—C2X—C10X | 113.9 (15) |
C3U—C2U—C1U | 99.4 (11) | C9X—C2X—C10X | 105.5 (12) |
C9U—C2U—C10U | 107.5 (12) | C1X—C2X—C3X | 102.6 (11) |
C3U—C2U—C10U | 112.3 (16) | C9X—C2X—C3X | 109.2 (18) |
C1U—C2U—C10U | 113.8 (16) | C10X—C2X—C3X | 115.1 (18) |
C8U—C3U—C4U | 112.9 (12) | C8X—C3X—C4X | 120 (2) |
C8U—C3U—C2U | 111.4 (11) | C8X—C3X—C2X | 108.7 (12) |
C4U—C3U—C2U | 105.7 (13) | C4X—C3X—C2X | 106.3 (14) |
C8U—C3U—H3U | 108.9 | C8X—C3X—H3X | 106.9 |
C4U—C3U—H3U | 108.9 | C4X—C3X—H3X | 106.9 |
C2U—C3U—H3U | 108.9 | C2X—C3X—H3X | 106.9 |
C3U—C4U—C5U | 104.7 (9) | C3X—C4X—C5X | 105.7 (11) |
C3U—C4U—H4U1 | 110.8 | C3X—C4X—H4X1 | 110.6 |
C5U—C4U—H4U1 | 110.8 | C5X—C4X—H4X1 | 110.6 |
C3U—C4U—H4U2 | 110.8 | C3X—C4X—H4X2 | 110.6 |
C5U—C4U—H4U2 | 110.8 | C5X—C4X—H4X2 | 110.6 |
H4U1—C4U—H4U2 | 108.9 | H4X1—C4X—H4X2 | 108.7 |
C4U—C5U—C1U | 106.4 (10) | C4X—C5X—C1X | 106.1 (10) |
C4U—C5U—H5U1 | 110.5 | C4X—C5X—H5X1 | 110.5 |
C1U—C5U—H5U1 | 110.5 | C1X—C5X—H5X1 | 110.5 |
C4U—C5U—H5U2 | 110.5 | C4X—C5X—H5X2 | 110.5 |
C1U—C5U—H5U2 | 110.5 | C1X—C5X—H5X2 | 110.5 |
H5U1—C5U—H5U2 | 108.6 | H5X1—C5X—H5X2 | 108.7 |
O1U—C6U—O2U | 117 (2) | O1X—C6X—O2X | 124.2 (13) |
O1U—C6U—C1U | 125.7 (15) | O1X—C6X—C1X | 121.1 (10) |
O2U—C6U—C1U | 117.6 (12) | O2X—C6X—C1X | 114.5 (9) |
C1U—C7U—H7U1 | 109.5 | C1X—C7X—H7X1 | 109.5 |
C1U—C7U—H7U2 | 109.5 | C1X—C7X—H7X2 | 109.5 |
H7U1—C7U—H7U2 | 109.5 | H7X1—C7X—H7X2 | 109.5 |
C1U—C7U—H7U3 | 109.5 | C1X—C7X—H7X3 | 109.5 |
H7U1—C7U—H7U3 | 109.5 | H7X1—C7X—H7X3 | 109.5 |
H7U2—C7U—H7U3 | 109.5 | H7X2—C7X—H7X3 | 109.5 |
O3U—C8U—O4U | 119.7 (13) | O3X—C8X—O4X | 123 (2) |
O3U—C8U—C3U | 124.5 (11) | O3X—C8X—C3X | 121.1 (13) |
O4U—C8U—C3U | 115.7 (9) | O4X—C8X—C3X | 115.4 (12) |
C2U—C9U—H9U1 | 109.5 | C2X—C9X—H9X1 | 109.5 |
C2U—C9U—H9U2 | 109.5 | C2X—C9X—H9X2 | 109.5 |
H9U1—C9U—H9U2 | 109.5 | H9X1—C9X—H9X2 | 109.5 |
C2U—C9U—H9U3 | 109.5 | C2X—C9X—H9X3 | 109.5 |
H9U1—C9U—H9U3 | 109.5 | H9X1—C9X—H9X3 | 109.5 |
H9U2—C9U—H9U3 | 109.5 | H9X2—C9X—H9X3 | 109.5 |
C2U—C10U—H10D | 109.5 | C2X—C10X—H10P | 109.5 |
C2U—C10U—H10E | 109.5 | C2X—C10X—H10Q | 109.5 |
H10D—C10U—H10E | 109.5 | H10P—C10X—H10Q | 109.5 |
C2U—C10U—H10F | 109.5 | C2X—C10X—H10R | 109.5 |
H10D—C10U—H10F | 109.5 | H10P—C10X—H10R | 109.5 |
H10E—C10U—H10F | 109.5 | H10Q—C10X—H10R | 109.5 |
C12B—N1B—C16B | 116.9 (3) | C12F—N1F—C16F | 116.9 (4) |
N1B—C12B—C13B | 123.7 (4) | C22F—N2F—C26F | 117.0 (3) |
N1B—C12B—H12B | 118.1 | N1F—C12F—C13F | 124.3 (4) |
C13B—C12B—H12B | 118.1 | N1F—C12F—H12F | 117.9 |
C12B—C13B—C14B | 119.7 (4) | C13F—C12F—H12F | 117.9 |
C12B—C13B—H13B | 120.1 | C12F—C13F—C14F | 118.8 (4) |
C14B—C13B—H13B | 120.1 | C12F—C13F—H13F | 120.6 |
C15B—C14B—C13B | 116.6 (4) | C14F—C13F—H13F | 120.6 |
C15B—C14B—C17B | 119.5 (4) | C15F—C14F—C13F | 117.5 (4) |
C13B—C14B—C17B | 123.9 (4) | C15F—C14F—C17F | 121.5 (4) |
C16B—C15B—C14B | 120.2 (4) | C13F—C14F—C17F | 121.0 (4) |
C16B—C15B—H15B | 119.9 | C14F—C15F—C16F | 119.6 (4) |
C14B—C15B—H15B | 119.9 | C14F—C15F—H15F | 120.2 |
N1B—C16B—C15B | 122.9 (4) | C16F—C15F—H15F | 120.2 |
N1B—C16B—H16B | 118.6 | N1F—C16F—C15F | 122.9 (4) |
C15B—C16B—H16B | 118.6 | N1F—C16F—H16F | 118.6 |
C14B—C17B—C27B | 115.1 (3) | C15F—C16F—H16F | 118.6 |
C14B—C17B—H17E | 108.5 | C27F—C17F—C14F | 111.7 (3) |
C27B—C17B—H17E | 108.5 | C27F—C17F—H17G | 109.3 |
C14B—C17B—H17F | 108.5 | C14F—C17F—H17G | 109.3 |
C27B—C17B—H17F | 108.5 | C27F—C17F—H17H | 109.3 |
H17E—C17B—H17F | 107.5 | C14F—C17F—H17H | 109.3 |
C22B—N2B—C26B | 116.5 (4) | H17G—C17F—H17H | 107.9 |
N2B—C22B—C23B | 123.3 (4) | N2F—C22F—C23F | 124.0 (4) |
N2B—C22B—H22B | 118.3 | N2F—C22F—H22F | 118.0 |
C23B—C22B—H22B | 118.3 | C23F—C22F—H22F | 118.0 |
C22B—C23B—C24B | 119.7 (4) | C22F—C23F—C24F | 119.3 (4) |
C22B—C23B—H23B | 120.2 | C22F—C23F—H23F | 120.4 |
C24B—C23B—H23B | 120.2 | C24F—C23F—H23F | 120.4 |
C23B—C24B—C25B | 117.4 (4) | C25F—C24F—C23F | 116.6 (3) |
C23B—C24B—C27B | 122.5 (4) | C25F—C24F—C27F | 119.8 (3) |
C25B—C24B—C27B | 120.0 (4) | C23F—C24F—C27F | 123.6 (3) |
C26B—C25B—C24B | 119.1 (4) | C26F—C25F—C24F | 120.5 (4) |
C26B—C25B—H25B | 120.5 | C26F—C25F—H25F | 119.7 |
C24B—C25B—H25B | 120.5 | C24F—C25F—H25F | 119.7 |
N2B—C26B—C25B | 123.9 (4) | N2F—C26F—C25F | 122.6 (4) |
N2B—C26B—H26B | 118.1 | N2F—C26F—H26F | 118.7 |
C25B—C26B—H26B | 118.1 | C25F—C26F—H26F | 118.7 |
C17B—C27B—C24B | 112.4 (3) | C17F—C27F—C24F | 115.3 (3) |
C17B—C27B—H27E | 109.1 | C17F—C27F—H27G | 108.4 |
C24B—C27B—H27E | 109.1 | C24F—C27F—H27G | 108.4 |
C17B—C27B—H27F | 109.1 | C17F—C27F—H27H | 108.4 |
C24B—C27B—H27F | 109.1 | C24F—C27F—H27H | 108.4 |
H27E—C27B—H27F | 107.9 | H27G—C27F—H27H | 107.5 |
C16V—N1V—C12V | 119.0 (18) | C12Y—N1Y—C16Y | 116.5 (19) |
N1V—C12V—C13V | 123.0 (19) | N1Y—C12Y—C13Y | 124 (2) |
N1V—C12V—H12V | 118.5 | N1Y—C12Y—H12Y | 117.9 |
C13V—C12V—H12V | 118.5 | C13Y—C12Y—H12Y | 117.9 |
C14V—C13V—C12V | 119.7 (18) | C14Y—C13Y—C12Y | 119 (2) |
C14V—C13V—H13V | 120.2 | C14Y—C13Y—H13Y | 120.5 |
C12V—C13V—H13V | 120.2 | C12Y—C13Y—H13Y | 120.5 |
C13V—C14V—C15V | 115.7 (16) | C13Y—C14Y—C15Y | 116.6 (17) |
C13V—C14V—C17V | 123.4 (15) | C13Y—C14Y—C17Y | 118.8 (16) |
C15V—C14V—C17V | 120.8 (14) | C15Y—C14Y—C17Y | 124.5 (16) |
C14V—C15V—C16V | 123.0 (18) | C16Y—C15Y—C14Y | 121.0 (18) |
C14V—C15V—H15V | 118.5 | C16Y—C15Y—H15Y | 119.5 |
C16V—C15V—H15V | 118.5 | C14Y—C15Y—H15Y | 119.5 |
N1V—C16V—C15V | 119.4 (18) | N1Y—C16Y—C15Y | 122.4 (19) |
N1V—C16V—H16V | 120.3 | N1Y—C16Y—H16Y | 118.8 |
C15V—C16V—H16V | 120.3 | C15Y—C16Y—H16Y | 118.8 |
C14V—C17V—C27V | 116.9 (15) | C14Y—C17Y—C27Y | 113.1 (16) |
C14V—C17V—H17I | 108.1 | C14Y—C17Y—H17K | 109.0 |
C27V—C17V—H17I | 108.1 | C27Y—C17Y—H17K | 109.0 |
C14V—C17V—H17J | 108.1 | C14Y—C17Y—H17L | 109.0 |
C27V—C17V—H17J | 108.1 | C27Y—C17Y—H17L | 109.0 |
H17I—C17V—H17J | 107.3 | H17K—C17Y—H17L | 107.8 |
C22V—N2V—C26V | 119.9 (19) | C22Y—N2Y—C26Y | 117.6 (19) |
N2V—C22V—C23V | 123 (2) | N2Y—C22Y—C23Y | 121 (2) |
N2V—C22V—H22V | 118.3 | N2Y—C22Y—H22Y | 119.4 |
C23V—C22V—H22V | 118.3 | C23Y—C22Y—H22Y | 119.4 |
C24V—C23V—C22V | 117 (2) | C24Y—C23Y—C22Y | 120 (2) |
C24V—C23V—H23V | 121.3 | C24Y—C23Y—H23Y | 119.8 |
C22V—C23V—H23V | 121.3 | C22Y—C23Y—H23Y | 119.8 |
C23V—C24V—C25V | 118.0 (17) | C25Y—C24Y—C23Y | 118.4 (18) |
C23V—C24V—C27V | 122.6 (16) | C25Y—C24Y—C27Y | 117.9 (15) |
C25V—C24V—C27V | 119.4 (16) | C23Y—C24Y—C27Y | 123.6 (17) |
C26V—C25V—C24V | 122.3 (18) | C26Y—C25Y—C24Y | 117.2 (18) |
C26V—C25V—H25V | 118.8 | C26Y—C25Y—H25Y | 121.4 |
C24V—C25V—H25V | 118.8 | C24Y—C25Y—H25Y | 121.4 |
N2V—C26V—C25V | 118.9 (19) | N2Y—C26Y—C25Y | 124.5 (19) |
N2V—C26V—H26V | 120.6 | N2Y—C26Y—H26Y | 117.7 |
C25V—C26V—H26V | 120.6 | C25Y—C26Y—H26Y | 117.7 |
C24V—C27V—C17V | 112.5 (16) | C24Y—C27Y—C17Y | 114.6 (15) |
C24V—C27V—H27I | 109.1 | C24Y—C27Y—H27K | 108.6 |
C17V—C27V—H27I | 109.1 | C17Y—C27Y—H27K | 108.6 |
C24V—C27V—H27J | 109.1 | C24Y—C27Y—H27L | 108.6 |
C17V—C27V—H27J | 109.1 | C17Y—C27Y—H27L | 108.6 |
H27I—C27V—H27J | 107.8 | H27K—C27Y—H27L | 107.6 |
C6C—C1C—C7C | 108.8 (3) | C6G—C1G—C7G | 110.9 (4) |
C6C—C1C—C5C | 112.2 (3) | C6G—C1G—C5G | 113.7 (3) |
C7C—C1C—C5C | 109.8 (3) | C7G—C1G—C5G | 108.9 (4) |
C6C—C1C—C2C | 110.9 (3) | C6G—C1G—C2G | 108.8 (3) |
C7C—C1C—C2C | 112.3 (3) | C7G—C1G—C2G | 112.0 (3) |
C5C—C1C—C2C | 102.6 (3) | C5G—C1G—C2G | 102.3 (3) |
C10C—C2C—C9C | 108.0 (3) | C10G—C2G—C9G | 108.4 (3) |
C10C—C2C—C1C | 114.2 (3) | C10G—C2G—C3G | 112.5 (3) |
C9C—C2C—C1C | 110.5 (3) | C9G—C2G—C3G | 109.6 (3) |
C10C—C2C—C3C | 111.3 (3) | C10G—C2G—C1G | 114.5 (3) |
C9C—C2C—C3C | 112.1 (3) | C9G—C2G—C1G | 109.9 (3) |
C1C—C2C—C3C | 100.6 (3) | C3G—C2G—C1G | 101.7 (3) |
C8C—C3C—C4C | 117.4 (4) | C8G—C3G—C4G | 116.8 (3) |
C8C—C3C—C2C | 110.2 (3) | C8G—C3G—C2G | 110.3 (3) |
C4C—C3C—C2C | 107.0 (3) | C4G—C3G—C2G | 105.5 (3) |
C8C—C3C—H3C1 | 107.3 | C8G—C3G—H3G1 | 108.0 |
C4C—C3C—H3C1 | 107.3 | C4G—C3G—H3G1 | 108.0 |
C2C—C3C—H3C1 | 107.3 | C2G—C3G—H3G1 | 108.0 |
C5C—C4C—C3C | 106.1 (3) | C3G—C4G—C5G | 106.4 (3) |
C5C—C4C—H4C1 | 110.5 | C3G—C4G—H4G1 | 110.4 |
C3C—C4C—H4C1 | 110.5 | C5G—C4G—H4G1 | 110.4 |
C5C—C4C—H4C2 | 110.5 | C3G—C4G—H4G2 | 110.4 |
C3C—C4C—H4C2 | 110.5 | C5G—C4G—H4G2 | 110.4 |
H4C1—C4C—H4C2 | 108.7 | H4G1—C4G—H4G2 | 108.6 |
C4C—C5C—C1C | 105.0 (3) | C1G—C5G—C4G | 106.5 (3) |
C4C—C5C—H5C1 | 110.7 | C1G—C5G—H5G1 | 110.4 |
C1C—C5C—H5C1 | 110.7 | C4G—C5G—H5G1 | 110.4 |
C4C—C5C—H5C2 | 110.7 | C1G—C5G—H5G2 | 110.4 |
C1C—C5C—H5C2 | 110.7 | C4G—C5G—H5G2 | 110.4 |
H5C1—C5C—H5C2 | 108.8 | H5G1—C5G—H5G2 | 108.6 |
O2C—C6C—O1C | 122.5 (3) | O2G—C6G—O1G | 122.4 (4) |
O2C—C6C—C1C | 124.5 (3) | O2G—C6G—C1G | 125.1 (4) |
O1C—C6C—C1C | 113.0 (3) | O1G—C6G—C1G | 112.4 (3) |
C1C—C7C—H7C1 | 109.5 | C1G—C7G—H7G1 | 109.5 |
C1C—C7C—H7C2 | 109.5 | C1G—C7G—H7G2 | 109.5 |
H7C1—C7C—H7C2 | 109.5 | H7G1—C7G—H7G2 | 109.5 |
C1C—C7C—H7C3 | 109.5 | C1G—C7G—H7G3 | 109.5 |
H7C1—C7C—H7C3 | 109.5 | H7G1—C7G—H7G3 | 109.5 |
H7C2—C7C—H7C3 | 109.5 | H7G2—C7G—H7G3 | 109.5 |
O4C—C8C—O3C | 123.1 (4) | O4G—C8G—O3G | 122.9 (4) |
O4C—C8C—C3C | 121.9 (4) | O4G—C8G—C3G | 121.2 (4) |
O3C—C8C—C3C | 114.9 (3) | O3G—C8G—C3G | 115.8 (4) |
C2C—C9C—H9C1 | 109.5 | C2G—C9G—H9G1 | 109.5 |
C2C—C9C—H9C2 | 109.5 | C2G—C9G—H9G2 | 109.5 |
H9C1—C9C—H9C2 | 109.5 | H9G1—C9G—H9G2 | 109.5 |
C2C—C9C—H9C3 | 109.5 | C2G—C9G—H9G3 | 109.5 |
H9C1—C9C—H9C3 | 109.5 | H9G1—C9G—H9G3 | 109.5 |
H9C2—C9C—H9C3 | 109.5 | H9G2—C9G—H9G3 | 109.5 |
C2C—C10C—H10G | 109.5 | C2G—C10G—H10S | 109.5 |
C2C—C10C—H10H | 109.5 | C2G—C10G—H10T | 109.5 |
H10G—C10C—H10H | 109.5 | H10S—C10G—H10T | 109.5 |
C2C—C10C—H10I | 109.5 | C2G—C10G—H10U | 109.5 |
H10G—C10C—H10I | 109.5 | H10S—C10G—H10U | 109.5 |
H10H—C10C—H10I | 109.5 | H10T—C10G—H10U | 109.5 |
C6W—O1W—H1W | 106.3 | C6Z—O1Z—H1Z | 121.6 |
C8W—O3W—H3W | 111.2 | C8Z—O3Z—H3Z | 116.8 |
C6W—C1W—C7W | 104 (2) | C6Z—C1Z—C7Z | 110.6 (13) |
C6W—C1W—C5W | 122 (2) | C6Z—C1Z—C2Z | 111.5 (10) |
C7W—C1W—C5W | 107.6 (14) | C7Z—C1Z—C2Z | 111.8 (11) |
C6W—C1W—C2W | 109.6 (12) | C6Z—C1Z—C5Z | 112.7 (11) |
C7W—C1W—C2W | 109.7 (14) | C7Z—C1Z—C5Z | 107.0 (11) |
C5W—C1W—C2W | 103.7 (14) | C2Z—C1Z—C5Z | 103.0 (12) |
C9W—C2W—C3W | 109.4 (16) | C9Z—C2Z—C10Z | 107.9 (12) |
C9W—C2W—C10W | 107.1 (12) | C9Z—C2Z—C1Z | 112.2 (14) |
C3W—C2W—C10W | 113.3 (16) | C10Z—C2Z—C1Z | 115.8 (14) |
C9W—C2W—C1W | 107.3 (17) | C9Z—C2Z—C3Z | 115.8 (17) |
C3W—C2W—C1W | 103.2 (12) | C10Z—C2Z—C3Z | 105.9 (17) |
C10W—C2W—C1W | 116.2 (16) | C1Z—C2Z—C3Z | 99.2 (11) |
C8W—C3W—C4W | 118.1 (12) | C8Z—C3Z—C4Z | 109 (2) |
C8W—C3W—C2W | 109.8 (10) | C8Z—C3Z—C2Z | 110.8 (12) |
C4W—C3W—C2W | 104.4 (13) | C4Z—C3Z—C2Z | 106.8 (16) |
C8W—C3W—H3W1 | 108.0 | C8Z—C3Z—H3Z1 | 110.0 |
C4W—C3W—H3W1 | 108.0 | C4Z—C3Z—H3Z1 | 110.0 |
C2W—C3W—H3W1 | 108.0 | C2Z—C3Z—H3Z1 | 110.0 |
C5W—C4W—C3W | 108.2 (10) | C3Z—C4Z—C5Z | 105.5 (11) |
C5W—C4W—H4W1 | 110.1 | C3Z—C4Z—H4Z1 | 110.6 |
C3W—C4W—H4W1 | 110.1 | C5Z—C4Z—H4Z1 | 110.6 |
C5W—C4W—H4W2 | 110.1 | C3Z—C4Z—H4Z2 | 110.6 |
C3W—C4W—H4W2 | 110.1 | C5Z—C4Z—H4Z2 | 110.6 |
H4W1—C4W—H4W2 | 108.4 | H4Z1—C4Z—H4Z2 | 108.8 |
C4W—C5W—C1W | 105.7 (10) | C4Z—C5Z—C1Z | 104.9 (10) |
C4W—C5W—H5W1 | 110.6 | C4Z—C5Z—H5Z1 | 110.8 |
C1W—C5W—H5W1 | 110.6 | C1Z—C5Z—H5Z1 | 110.8 |
C4W—C5W—H5W2 | 110.6 | C4Z—C5Z—H5Z2 | 110.8 |
C1W—C5W—H5W2 | 110.6 | C1Z—C5Z—H5Z2 | 110.8 |
H5W1—C5W—H5W2 | 108.7 | H5Z1—C5Z—H5Z2 | 108.8 |
O2W—C6W—O1W | 120 (2) | O2Z—C6Z—O1Z | 120.2 (14) |
O2W—C6W—C1W | 123.9 (15) | O2Z—C6Z—C1Z | 124.3 (11) |
O1W—C6W—C1W | 116.3 (12) | O1Z—C6Z—C1Z | 115.4 (9) |
C1W—C7W—H7W1 | 109.5 | C1Z—C7Z—H7Z1 | 109.5 |
C1W—C7W—H7W2 | 109.5 | C1Z—C7Z—H7Z2 | 109.5 |
H7W1—C7W—H7W2 | 109.5 | H7Z1—C7Z—H7Z2 | 109.5 |
C1W—C7W—H7W3 | 109.5 | C1Z—C7Z—H7Z3 | 109.5 |
H7W1—C7W—H7W3 | 109.5 | H7Z1—C7Z—H7Z3 | 109.5 |
H7W2—C7W—H7W3 | 109.5 | H7Z2—C7Z—H7Z3 | 109.5 |
O4W—C8W—O3W | 118.6 (13) | O4Z—C8Z—O3Z | 123 (2) |
O4W—C8W—C3W | 124.9 (11) | O4Z—C8Z—C3Z | 122.0 (14) |
O3W—C8W—C3W | 116.4 (9) | O3Z—C8Z—C3Z | 115.2 (12) |
C2W—C9W—H9W1 | 109.5 | C2Z—C9Z—H9Z1 | 109.5 |
C2W—C9W—H9W2 | 109.5 | C2Z—C9Z—H9Z2 | 109.5 |
H9W1—C9W—H9W2 | 109.5 | H9Z1—C9Z—H9Z2 | 109.5 |
C2W—C9W—H9W3 | 109.5 | C2Z—C9Z—H9Z3 | 109.5 |
H9W1—C9W—H9W3 | 109.5 | H9Z1—C9Z—H9Z3 | 109.5 |
H9W2—C9W—H9W3 | 109.5 | H9Z2—C9Z—H9Z3 | 109.5 |
C2W—C10W—H10J | 109.5 | C2Z—C10Z—H10V | 109.5 |
C2W—C10W—H10K | 109.5 | C2Z—C10Z—H10W | 109.5 |
H10J—C10W—H10K | 109.5 | H10V—C10Z—H10W | 109.5 |
C2W—C10W—H10L | 109.5 | C2Z—C10Z—H10$ | 109.5 |
H10J—C10W—H10L | 109.5 | H10V—C10Z—H10$ | 109.5 |
H10K—C10W—H10L | 109.5 | H10W—C10Z—H10$ | 109.5 |
C16D—N1D—C12D | 117.5 (3) | C12H—N1H—C16H | 116.7 (3) |
C22D—N2D—C26D | 116.9 (3) | C22H—N2H—C26H | 117.7 (3) |
N1D—C12D—C13D | 122.8 (3) | N1H—C12H—C13H | 123.5 (3) |
N1D—C12D—H12D | 118.6 | N1H—C12H—H12H | 118.3 |
C13D—C12D—H12D | 118.6 | C13H—C12H—H12H | 118.3 |
C12D—C13D—C14D | 120.4 (3) | C12H—C13H—C14H | 120.1 (3) |
C12D—C13D—H13D | 119.8 | C12H—C13H—H13H | 119.9 |
C14D—C13D—H13D | 119.8 | C14H—C13H—H13H | 119.9 |
C13D—C14D—C15D | 116.6 (3) | C13H—C14H—C15H | 116.4 (3) |
C13D—C14D—C17D | 124.1 (3) | C13H—C14H—C17H | 124.0 (3) |
C15D—C14D—C17D | 119.4 (3) | C15H—C14H—C17H | 119.6 (3) |
C16D—C15D—C14D | 119.5 (3) | C16H—C15H—C14H | 119.7 (3) |
C16D—C15D—H15D | 120.2 | C16H—C15H—H15H | 120.1 |
C14D—C15D—H15D | 120.2 | C14H—C15H—H15H | 120.1 |
N1D—C16D—C15D | 123.2 (3) | N1H—C16H—C15H | 123.5 (3) |
N1D—C16D—H16D | 118.4 | N1H—C16H—H16H | 118.2 |
C15D—C16D—H16D | 118.4 | C15H—C16H—H16H | 118.2 |
C14D—C17D—C27D | 115.4 (2) | C14H—C17H—C27H | 115.4 (2) |
C14D—C17D—H17C | 108.4 | C14H—C17H—H17A | 108.4 |
C27D—C17D—H17C | 108.4 | C27H—C17H—H17A | 108.4 |
C14D—C17D—H17D | 108.4 | C14H—C17H—H17B | 108.4 |
C27D—C17D—H17D | 108.4 | C27H—C17H—H17B | 108.4 |
H17C—C17D—H17D | 107.5 | H17A—C17H—H17B | 107.5 |
N2D—C22D—C23D | 123.3 (3) | N2H—C22H—C23H | 122.3 (3) |
N2D—C22D—H22D | 118.3 | N2H—C22H—H22H | 118.9 |
C23D—C22D—H22D | 118.3 | C23H—C22H—H22H | 118.9 |
C24D—C23D—C22D | 119.3 (3) | C24H—C23H—C22H | 120.0 (3) |
C24D—C23D—H23D | 120.3 | C24H—C23H—H23H | 120.0 |
C22D—C23D—H23D | 120.3 | C22H—C23H—H23H | 120.0 |
C25D—C24D—C23D | 116.9 (3) | C23H—C24H—C25H | 117.0 (3) |
C25D—C24D—C27D | 119.4 (3) | C23H—C24H—C27H | 123.7 (3) |
C23D—C24D—C27D | 123.7 (3) | C25H—C24H—C27H | 119.3 (3) |
C26D—C25D—C24D | 120.1 (3) | C26H—C25H—C24H | 119.7 (3) |
C26D—C25D—H25D | 119.9 | C26H—C25H—H25H | 120.2 |
C24D—C25D—H25D | 119.9 | C24H—C25H—H25H | 120.2 |
N2D—C26D—C25D | 123.4 (3) | N2H—C26H—C25H | 123.3 (3) |
N2D—C26D—H26D | 118.3 | N2H—C26H—H26H | 118.3 |
C25D—C26D—H26D | 118.3 | C25H—C26H—H26H | 118.3 |
C24D—C27D—C17D | 115.1 (2) | C24H—C27H—C17H | 115.1 (2) |
C24D—C27D—H27C | 108.5 | C24H—C27H—H27A | 108.5 |
C17D—C27D—H27C | 108.5 | C17H—C27H—H27A | 108.5 |
C24D—C27D—H27D | 108.5 | C24H—C27H—H27B | 108.5 |
C17D—C27D—H27D | 108.5 | C17H—C27H—H27B | 108.5 |
H27C—C27D—H27D | 107.5 | H27A—C27H—H27B | 107.5 |
| | | |
C6A—C1A—C2A—C10A | −73.4 (4) | C7E—C1E—C2E—C9E | 163.1 (4) |
C7A—C1A—C2A—C10A | 45.7 (5) | C6E—C1E—C2E—C9E | 43.6 (5) |
C5A—C1A—C2A—C10A | 162.8 (4) | C5E—C1E—C2E—C9E | −78.6 (4) |
C6A—C1A—C2A—C9A | 48.7 (4) | C7E—C1E—C2E—C10E | 41.2 (5) |
C7A—C1A—C2A—C9A | 167.7 (3) | C6E—C1E—C2E—C10E | −78.3 (4) |
C5A—C1A—C2A—C9A | −75.1 (4) | C5E—C1E—C2E—C10E | 159.5 (3) |
C6A—C1A—C2A—C3A | 165.3 (3) | C7E—C1E—C2E—C3E | −80.1 (4) |
C7A—C1A—C2A—C3A | −75.7 (4) | C6E—C1E—C2E—C3E | 160.4 (4) |
C5A—C1A—C2A—C3A | 41.4 (4) | C5E—C1E—C2E—C3E | 38.2 (4) |
C10A—C2A—C3A—C8A | 76.8 (5) | C9E—C2E—C3E—C8E | −47.3 (4) |
C9A—C2A—C3A—C8A | −44.6 (5) | C10E—C2E—C3E—C8E | 74.9 (5) |
C1A—C2A—C3A—C8A | −160.9 (4) | C1E—C2E—C3E—C8E | −164.7 (4) |
C10A—C2A—C3A—C4A | −158.6 (4) | C9E—C2E—C3E—C4E | 76.2 (4) |
C9A—C2A—C3A—C4A | 80.0 (4) | C10E—C2E—C3E—C4E | −161.6 (4) |
C1A—C2A—C3A—C4A | −36.2 (4) | C1E—C2E—C3E—C4E | −41.2 (4) |
C8A—C3A—C4A—C5A | 139.3 (4) | C8E—C3E—C4E—C5E | 151.1 (3) |
C2A—C3A—C4A—C5A | 16.9 (5) | C2E—C3E—C4E—C5E | 29.1 (4) |
C3A—C4A—C5A—C1A | 9.7 (5) | C3E—C4E—C5E—C1E | −4.5 (5) |
C6A—C1A—C5A—C4A | −152.1 (4) | C7E—C1E—C5E—C4E | 98.6 (4) |
C7A—C1A—C5A—C4A | 86.6 (4) | C6E—C1E—C5E—C4E | −141.1 (4) |
C2A—C1A—C5A—C4A | −32.2 (4) | C2E—C1E—C5E—C4E | −21.3 (4) |
C7A—C1A—C6A—O1A | −57.3 (5) | C7E—C1E—C6E—O1E | −31.6 (6) |
C5A—C1A—C6A—O1A | −179.8 (4) | C5E—C1E—C6E—O1E | −152.9 (5) |
C2A—C1A—C6A—O1A | 64.5 (5) | C2E—C1E—C6E—O1E | 90.4 (6) |
C7A—C1A—C6A—O2A | 124.6 (4) | C7E—C1E—C6E—O2E | 149.4 (5) |
C5A—C1A—C6A—O2A | 2.1 (5) | C5E—C1E—C6E—O2E | 28.0 (6) |
C2A—C1A—C6A—O2A | −113.6 (4) | C2E—C1E—C6E—O2E | −88.7 (5) |
C4A—C3A—C8A—O3A | −19.5 (7) | C4E—C3E—C8E—O3E | −17.0 (5) |
C2A—C3A—C8A—O3A | 100.0 (7) | C2E—C3E—C8E—O3E | 101.0 (4) |
C4A—C3A—C8A—O4A | 163.1 (5) | C4E—C3E—C8E—O4E | 162.4 (3) |
C2A—C3A—C8A—O4A | −77.4 (5) | C2E—C3E—C8E—O4E | −79.7 (4) |
C6U—C1U—C2U—C9U | 48 (2) | C6X—C1X—C2X—C9X | 45.6 (17) |
C7U—C1U—C2U—C9U | 168 (2) | C7X—C1X—C2X—C9X | 168.9 (15) |
C5U—C1U—C2U—C9U | −75.0 (18) | C5X—C1X—C2X—C9X | −75.2 (15) |
C6U—C1U—C2U—C3U | 164.8 (17) | C6X—C1X—C2X—C10X | −72.9 (16) |
C7U—C1U—C2U—C3U | −75 (2) | C7X—C1X—C2X—C10X | 50.4 (18) |
C5U—C1U—C2U—C3U | 41.8 (17) | C5X—C1X—C2X—C10X | 166.2 (15) |
C6U—C1U—C2U—C10U | −76 (2) | C6X—C1X—C2X—C3X | 162.0 (16) |
C7U—C1U—C2U—C10U | 45 (2) | C7X—C1X—C2X—C3X | −75 (2) |
C5U—C1U—C2U—C10U | 161.4 (17) | C5X—C1X—C2X—C3X | 41.2 (18) |
C9U—C2U—C3U—C8U | −45.9 (19) | C1X—C2X—C3X—C8X | −162.2 (15) |
C1U—C2U—C3U—C8U | −165.6 (13) | C9X—C2X—C3X—C8X | −45 (2) |
C10U—C2U—C3U—C8U | 73.8 (17) | C10X—C2X—C3X—C8X | 74 (2) |
C9U—C2U—C3U—C4U | 77.1 (17) | C1X—C2X—C3X—C4X | −31 (3) |
C1U—C2U—C3U—C4U | −42.6 (18) | C9X—C2X—C3X—C4X | 86 (2) |
C10U—C2U—C3U—C4U | −163.3 (16) | C10X—C2X—C3X—C4X | −155 (2) |
C8U—C3U—C4U—C5U | 148.9 (16) | C8X—C3X—C4X—C5X | 132 (2) |
C2U—C3U—C4U—C5U | 27 (2) | C2X—C3X—C4X—C5X | 8 (3) |
C3U—C4U—C5U—C1U | 0 (2) | C3X—C4X—C5X—C1X | 18 (3) |
C6U—C1U—C5U—C4U | −148.6 (18) | C6X—C1X—C5X—C4X | −156 (2) |
C7U—C1U—C5U—C4U | 93 (2) | C7X—C1X—C5X—C4X | 83 (2) |
C2U—C1U—C5U—C4U | −27 (2) | C2X—C1X—C5X—C4X | −37 (2) |
C7U—C1U—C6U—O1U | −32 (3) | C7X—C1X—C6X—O1X | −62.8 (17) |
C2U—C1U—C6U—O1U | 92 (3) | C5X—C1X—C6X—O1X | 176.7 (16) |
C5U—C1U—C6U—O1U | −151 (3) | C2X—C1X—C6X—O1X | 63.1 (18) |
C7U—C1U—C6U—O2U | 147 (3) | C7X—C1X—C6X—O2X | 121.8 (15) |
C2U—C1U—C6U—O2U | −90 (3) | C5X—C1X—C6X—O2X | 1.4 (18) |
C5U—C1U—C6U—O2U | 28 (3) | C2X—C1X—C6X—O2X | −112.3 (15) |
C4U—C3U—C8U—O3U | −16 (2) | C4X—C3X—C8X—O3X | −40 (3) |
C2U—C3U—C8U—O3U | 102.9 (18) | C2X—C3X—C8X—O3X | 83 (3) |
C4U—C3U—C8U—O4U | 160.7 (17) | C4X—C3X—C8X—O4X | 147 (3) |
C2U—C3U—C8U—O4U | −80.5 (18) | C2X—C3X—C8X—O4X | −90 (3) |
C16B—N1B—C12B—C13B | 0.1 (6) | C16F—N1F—C12F—C13F | 0.8 (7) |
N1B—C12B—C13B—C14B | 0.1 (7) | N1F—C12F—C13F—C14F | 0.1 (7) |
C12B—C13B—C14B—C15B | −0.4 (6) | C12F—C13F—C14F—C15F | −1.3 (6) |
C12B—C13B—C14B—C17B | 177.3 (4) | C12F—C13F—C14F—C17F | 179.0 (4) |
C13B—C14B—C15B—C16B | 0.6 (6) | C13F—C14F—C15F—C16F | 1.6 (6) |
C17B—C14B—C15B—C16B | −177.2 (4) | C17F—C14F—C15F—C16F | −178.6 (4) |
C12B—N1B—C16B—C15B | 0.1 (6) | C12F—N1F—C16F—C15F | −0.4 (6) |
C14B—C15B—C16B—N1B | −0.5 (6) | C14F—C15F—C16F—N1F | −0.8 (7) |
C15B—C14B—C17B—C27B | 175.9 (4) | C15F—C14F—C17F—C27F | −99.4 (5) |
C13B—C14B—C17B—C27B | −1.7 (6) | C13F—C14F—C17F—C27F | 80.3 (5) |
C26B—N2B—C22B—C23B | 0.1 (6) | C26F—N2F—C22F—C23F | −0.1 (6) |
N2B—C22B—C23B—C24B | 1.8 (6) | N2F—C22F—C23F—C24F | 0.8 (7) |
C22B—C23B—C24B—C25B | −2.9 (6) | C22F—C23F—C24F—C25F | −1.4 (6) |
C22B—C23B—C24B—C27B | 177.2 (4) | C22F—C23F—C24F—C27F | 178.4 (4) |
C23B—C24B—C25B—C26B | 2.2 (6) | C23F—C24F—C25F—C26F | 1.4 (6) |
C27B—C24B—C25B—C26B | −177.8 (4) | C27F—C24F—C25F—C26F | −178.4 (4) |
C22B—N2B—C26B—C25B | −0.8 (6) | C22F—N2F—C26F—C25F | 0.1 (6) |
C24B—C25B—C26B—N2B | −0.4 (7) | C24F—C25F—C26F—N2F | −0.8 (6) |
C14B—C17B—C27B—C24B | −178.4 (4) | C14F—C17F—C27F—C24F | 176.5 (3) |
C23B—C24B—C27B—C17B | 102.9 (5) | C25F—C24F—C27F—C17F | −177.4 (4) |
C25B—C24B—C27B—C17B | −77.0 (5) | C23F—C24F—C27F—C17F | 2.7 (5) |
C16V—N1V—C12V—C13V | −1.7 (18) | C16Y—N1Y—C12Y—C13Y | −1.8 (18) |
N1V—C12V—C13V—C14V | −1.0 (16) | N1Y—C12Y—C13Y—C14Y | 0.2 (17) |
C12V—C13V—C14V—C15V | 0 (3) | C12Y—C13Y—C14Y—C15Y | 1 (3) |
C12V—C13V—C14V—C17V | 177.7 (16) | C12Y—C13Y—C14Y—C17Y | −179.7 (15) |
C13V—C14V—C15V—C16V | 3 (3) | C13Y—C14Y—C15Y—C16Y | −1 (3) |
C17V—C14V—C15V—C16V | −175 (2) | C17Y—C14Y—C15Y—C16Y | −180 (2) |
C12V—N1V—C16V—C15V | 5 (3) | C12Y—N1Y—C16Y—C15Y | 2 (3) |
C14V—C15V—C16V—N1V | −5 (3) | C14Y—C15Y—C16Y—N1Y | −1 (4) |
C13V—C14V—C17V—C27V | 7 (3) | C13Y—C14Y—C17Y—C27Y | −78 (3) |
C15V—C14V—C17V—C27V | −176 (2) | C15Y—C14Y—C17Y—C27Y | 101 (3) |
C26V—N2V—C22V—C23V | −0.2 (18) | C26Y—N2Y—C22Y—C23Y | 0.0 (17) |
N2V—C22V—C23V—C24V | −0.6 (16) | N2Y—C22Y—C23Y—C24Y | 0.1 (16) |
C22V—C23V—C24V—C25V | −1 (3) | C22Y—C23Y—C24Y—C25Y | −4 (3) |
C22V—C23V—C24V—C27V | 178.3 (16) | C22Y—C23Y—C24Y—C27Y | 179.3 (16) |
C23V—C24V—C25V—C26V | 4 (3) | C23Y—C24Y—C25Y—C26Y | 8 (3) |
C27V—C24V—C25V—C26V | −176 (2) | C27Y—C24Y—C25Y—C26Y | −175 (2) |
C22V—N2V—C26V—C25V | 3 (3) | C22Y—N2Y—C26Y—C25Y | 4 (3) |
C24V—C25V—C26V—N2V | −5 (3) | C24Y—C25Y—C26Y—N2Y | −9 (3) |
C23V—C24V—C27V—C17V | 78 (3) | C25Y—C24Y—C27Y—C17Y | 179 (2) |
C25V—C24V—C27V—C17V | −102 (2) | C23Y—C24Y—C27Y—C17Y | −4 (3) |
C14V—C17V—C27V—C24V | 177.3 (18) | C14Y—C17Y—C27Y—C24Y | −176.3 (17) |
C6C—C1C—C2C—C10C | −79.0 (4) | C6G—C1G—C2G—C10G | −76.4 (4) |
C7C—C1C—C2C—C10C | 43.1 (4) | C7G—C1G—C2G—C10G | 46.5 (5) |
C5C—C1C—C2C—C10C | 161.0 (3) | C5G—C1G—C2G—C10G | 163.0 (3) |
C6C—C1C—C2C—C9C | 43.1 (4) | C6G—C1G—C2G—C9G | 45.8 (4) |
C7C—C1C—C2C—C9C | 165.2 (3) | C7G—C1G—C2G—C9G | 168.7 (4) |
C5C—C1C—C2C—C9C | −76.9 (4) | C5G—C1G—C2G—C9G | −74.8 (3) |
C6C—C1C—C2C—C3C | 161.7 (3) | C6G—C1G—C2G—C3G | 161.9 (3) |
C7C—C1C—C2C—C3C | −76.2 (4) | C7G—C1G—C2G—C3G | −75.1 (4) |
C5C—C1C—C2C—C3C | 41.7 (3) | C5G—C1G—C2G—C3G | 41.3 (3) |
C10C—C2C—C3C—C8C | 81.1 (4) | C10G—C2G—C3G—C8G | 73.0 (4) |
C9C—C2C—C3C—C8C | −40.0 (5) | C9G—C2G—C3G—C8G | −47.7 (4) |
C1C—C2C—C3C—C8C | −157.4 (4) | C1G—C2G—C3G—C8G | −164.0 (3) |
C10C—C2C—C3C—C4C | −150.2 (3) | C10G—C2G—C3G—C4G | −160.0 (3) |
C9C—C2C—C3C—C4C | 88.6 (4) | C9G—C2G—C3G—C4G | 79.3 (4) |
C1C—C2C—C3C—C4C | −28.8 (4) | C1G—C2G—C3G—C4G | −37.0 (3) |
C8C—C3C—C4C—C5C | 129.2 (4) | C8G—C3G—C4G—C5G | 141.1 (3) |
C2C—C3C—C4C—C5C | 4.8 (4) | C2G—C3G—C4G—C5G | 18.2 (4) |
C3C—C4C—C5C—C1C | 21.9 (4) | C6G—C1G—C5G—C4G | −148.1 (3) |
C6C—C1C—C5C—C4C | −159.5 (3) | C7G—C1G—C5G—C4G | 87.7 (4) |
C7C—C1C—C5C—C4C | 79.3 (4) | C2G—C1G—C5G—C4G | −30.9 (4) |
C2C—C1C—C5C—C4C | −40.3 (4) | C3G—C4G—C5G—C1G | 8.3 (4) |
C7C—C1C—C6C—O2C | 131.9 (4) | C7G—C1G—C6G—O2G | 139.6 (6) |
C5C—C1C—C6C—O2C | 10.1 (5) | C5G—C1G—C6G—O2G | 16.5 (7) |
C2C—C1C—C6C—O2C | −104.0 (4) | C2G—C1G—C6G—O2G | −96.8 (6) |
C7C—C1C—C6C—O1C | −48.8 (4) | C7G—C1G—C6G—O1G | −43.0 (6) |
C5C—C1C—C6C—O1C | −170.6 (3) | C5G—C1G—C6G—O1G | −166.2 (5) |
C2C—C1C—C6C—O1C | 75.3 (4) | C2G—C1G—C6G—O1G | 80.6 (5) |
C4C—C3C—C8C—O4C | 150.8 (7) | C4G—C3G—C8G—O4G | 170.2 (4) |
C2C—C3C—C8C—O4C | −86.4 (7) | C2G—C3G—C8G—O4G | −69.4 (5) |
C4C—C3C—C8C—O3C | −31.2 (7) | C4G—C3G—C8G—O3G | −12.4 (5) |
C2C—C3C—C8C—O3C | 91.5 (6) | C2G—C3G—C8G—O3G | 108.0 (4) |
C6W—C1W—C2W—C9W | 54 (2) | C6Z—C1Z—C2Z—C9Z | 42.9 (18) |
C7W—C1W—C2W—C9W | 168 (2) | C7Z—C1Z—C2Z—C9Z | 167.3 (15) |
C5W—C1W—C2W—C9W | −77.2 (18) | C5Z—C1Z—C2Z—C9Z | −78.2 (16) |
C6W—C1W—C2W—C3W | 169.8 (18) | C6Z—C1Z—C2Z—C10Z | −81.5 (16) |
C7W—C1W—C2W—C3W | −76 (2) | C7Z—C1Z—C2Z—C10Z | 42.8 (18) |
C5W—C1W—C2W—C3W | 38.3 (19) | C5Z—C1Z—C2Z—C10Z | 157.4 (15) |
C6W—C1W—C2W—C10W | −66 (2) | C6Z—C1Z—C2Z—C3Z | 165.8 (15) |
C7W—C1W—C2W—C10W | 48 (2) | C7Z—C1Z—C2Z—C3Z | −69.9 (18) |
C5W—C1W—C2W—C10W | 163.0 (17) | C5Z—C1Z—C2Z—C3Z | 44.7 (16) |
C9W—C2W—C3W—C8W | −48.3 (18) | C9Z—C2Z—C3Z—C8Z | −37 (2) |
C10W—C2W—C3W—C8W | 71.2 (17) | C10Z—C2Z—C3Z—C8Z | 82 (2) |
C1W—C2W—C3W—C8W | −162.3 (14) | C1Z—C2Z—C3Z—C8Z | −157.3 (15) |
C9W—C2W—C3W—C4W | 79.3 (17) | C9Z—C2Z—C3Z—C4Z | 82 (3) |
C10W—C2W—C3W—C4W | −161.3 (16) | C10Z—C2Z—C3Z—C4Z | −159 (3) |
C1W—C2W—C3W—C4W | −34.8 (19) | C1Z—C2Z—C3Z—C4Z | −38 (3) |
C8W—C3W—C4W—C5W | 140.4 (17) | C8Z—C3Z—C4Z—C5Z | 137 (3) |
C2W—C3W—C4W—C5W | 18 (2) | C2Z—C3Z—C4Z—C5Z | 17 (4) |
C3W—C4W—C5W—C1W | 6 (2) | C3Z—C4Z—C5Z—C1Z | 11 (4) |
C6W—C1W—C5W—C4W | −151 (2) | C6Z—C1Z—C5Z—C4Z | −156 (3) |
C7W—C1W—C5W—C4W | 89 (2) | C7Z—C1Z—C5Z—C4Z | 82 (3) |
C2W—C1W—C5W—C4W | −27 (2) | C2Z—C1Z—C5Z—C4Z | −36 (3) |
C7W—C1W—C6W—O2W | 149 (3) | C7Z—C1Z—C6Z—O2Z | 131.6 (17) |
C5W—C1W—C6W—O2W | 28 (4) | C2Z—C1Z—C6Z—O2Z | −103.4 (17) |
C2W—C1W—C6W—O2W | −93 (4) | C5Z—C1Z—C6Z—O2Z | 12 (2) |
C7W—C1W—C6W—O1W | −31 (3) | C7Z—C1Z—C6Z—O1Z | −52.0 (17) |
C5W—C1W—C6W—O1W | −152 (4) | C2Z—C1Z—C6Z—O1Z | 73.0 (17) |
C2W—C1W—C6W—O1W | 87 (4) | C5Z—C1Z—C6Z—O1Z | −171.7 (16) |
C4W—C3W—C8W—O4W | 173.1 (19) | C4Z—C3Z—C8Z—O4Z | 145 (3) |
C2W—C3W—C8W—O4W | −67 (2) | C2Z—C3Z—C8Z—O4Z | −97 (3) |
C4W—C3W—C8W—O3W | −11 (2) | C4Z—C3Z—C8Z—O3Z | −34 (3) |
C2W—C3W—C8W—O3W | 109.0 (16) | C2Z—C3Z—C8Z—O3Z | 83 (3) |
C16D—N1D—C12D—C13D | 0.3 (5) | C16H—N1H—C12H—C13H | −0.4 (5) |
N1D—C12D—C13D—C14D | −1.5 (5) | N1H—C12H—C13H—C14H | −0.9 (5) |
C12D—C13D—C14D—C15D | 1.6 (5) | C12H—C13H—C14H—C15H | 1.5 (5) |
C12D—C13D—C14D—C17D | −178.1 (3) | C12H—C13H—C14H—C17H | −177.9 (3) |
C13D—C14D—C15D—C16D | −0.7 (5) | C13H—C14H—C15H—C16H | −0.8 (5) |
C17D—C14D—C15D—C16D | 179.0 (3) | C17H—C14H—C15H—C16H | 178.6 (3) |
C12D—N1D—C16D—C15D | 0.6 (5) | C12H—N1H—C16H—C15H | 1.2 (5) |
C14D—C15D—C16D—N1D | −0.4 (6) | C14H—C15H—C16H—N1H | −0.6 (6) |
C13D—C14D—C17D—C27D | 4.5 (4) | C13H—C14H—C17H—C27H | 1.7 (4) |
C15D—C14D—C17D—C27D | −175.2 (3) | C15H—C14H—C17H—C27H | −177.6 (3) |
C26D—N2D—C22D—C23D | −0.1 (5) | C26H—N2H—C22H—C23H | 0.2 (5) |
N2D—C22D—C23D—C24D | 0.7 (5) | N2H—C22H—C23H—C24H | 0.5 (5) |
C22D—C23D—C24D—C25D | −1.0 (5) | C22H—C23H—C24H—C25H | −0.6 (5) |
C22D—C23D—C24D—C27D | 178.4 (3) | C22H—C23H—C24H—C27H | 178.5 (3) |
C23D—C24D—C25D—C26D | 0.8 (5) | C23H—C24H—C25H—C26H | 0.0 (5) |
C27D—C24D—C25D—C26D | −178.6 (3) | C27H—C24H—C25H—C26H | −179.1 (3) |
C22D—N2D—C26D—C25D | −0.1 (5) | C22H—N2H—C26H—C25H | −0.8 (5) |
C24D—C25D—C26D—N2D | −0.3 (6) | C24H—C25H—C26H—N2H | 0.7 (6) |
C25D—C24D—C27D—C17D | 177.9 (3) | C23H—C24H—C27H—C17H | −5.0 (4) |
C23D—C24D—C27D—C17D | −1.4 (4) | C25H—C24H—C27H—C17H | 174.1 (3) |
C14D—C17D—C27D—C24D | 179.5 (3) | C14H—C17H—C27H—C24H | 179.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2A···N1B | 0.84 | 1.82 | 2.656 (4) | 173 |
O1C—H1C···N2B | 0.84 | 1.80 | 2.614 (4) | 163 |
O3C—H3C···N1D | 0.84 | 1.82 | 2.652 (6) | 174 |
O2E—H2E···N2D | 0.84 | 1.85 | 2.686 (6) | 175 |
O4E—H4E···N1F | 0.84 | 1.82 | 2.635 (5) | 162 |
O3G—H3G···N2F | 0.84 | 1.84 | 2.658 (4) | 166 |
O1G—H1G···N1H | 0.84 | 1.83 | 2.650 (7) | 167 |
O4A—H4A···N2Hi | 0.84 | 1.80 | 2.639 (6) | 176 |
C13F—H13F···O3Eii | 0.95 | 2.55 | 3.332 (6) | 140 |
C17B—H17E···O1Aii | 0.99 | 2.47 | 3.308 (5) | 142 |
C25B—H25B···O2Ciii | 0.95 | 2.50 | 3.272 (5) | 138 |
C27F—H27G···O4Giii | 0.99 | 2.30 | 3.182 (5) | 147 |
C16B—H16B···O3Eiv | 0.95 | 2.56 | 3.382 (5) | 145 |
C22D—H22D···O3Av | 0.95 | 2.56 | 3.429 (9) | 152 |
C22H—H22H···O1Ev | 0.95 | 2.52 | 3.386 (5) | 151 |
C26F—H26F···O2Cv | 0.95 | 2.48 | 3.279 (5) | 142 |
C12H—H12H···O4Cvi | 0.95 | 2.50 | 3.379 (10) | 153 |
O2U—H2U···N2Hi | 0.84 | 1.87 | 2.71 (4) | 180 |
O4U—H4U···N2V | 0.84 | 1.80 | 2.64 (2) | 180 |
O3W—H3W···N1V | 0.84 | 1.83 | 2.67 (2) | 180 |
O1W—H1W···N1D | 0.84 | 1.90 | 2.74 (4) | 180 |
O4X—H4X···N2D | 0.84 | 1.70 | 2.54 (4) | 180 |
O2X—H2X···N2Y | 0.84 | 1.80 | 2.64 (2) | 180 |
O1Z—H1Z···N1Y | 0.84 | 1.72 | 2.56 (2) | 180 |
O3Z—H3Z···N1H | 0.84 | 1.83 | 2.67 (4) | 180 |
O2U—H2U···N2Hi | 0.84 | 1.87 | 2.71 (4) | 180 |
Symmetry codes: (i) x+3, y+3, z+2; (ii) x−1, y, z; (iii) x+1, y, z; (iv) x+1, y+1, z+1; (v) x−1, y−1, z−1; (vi) x−2, y−2, z−1. |
(IV) (1
R,3S)-Camphoric acid–1,4-diazabicyclo[2.2.2]octane–water (1/1/1)
top
Crystal data top
C6H13N2·C10H15O4·H2O | F(000) = 720 |
Mr = 330.42 | Dx = 1.272 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1768 reflections |
a = 7.0310 (3) Å | θ = 2.6–25.0° |
b = 11.2520 (5) Å | µ = 0.09 mm−1 |
c = 21.8177 (12) Å | T = 150 K |
V = 1726.06 (14) Å3 | Plate, colourless |
Z = 4 | 0.38 × 0.32 × 0.11 mm |
Data collection top
Kappa-CCD diffractometer | 1423 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.058 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
φ scans, and ω scans with κ offsets | h = 0→8 |
7008 measured reflections | k = 0→13 |
1768 independent reflections | l = 0→25 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-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 parameters | Δρmax = 0.31 e Å−3 |
154 restraints | Δρmin = −0.17 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.3946 (4) | 0.2585 (2) | 0.11569 (12) | 0.0464 (7) | |
O2 | 0.0905 (3) | 0.3091 (3) | 0.11619 (11) | 0.0496 (7) | |
O3 | 0.4852 (6) | 0.2501 (3) | 0.38038 (16) | 0.0531 (9) | 0.828 (5) |
O4 | 0.1745 (5) | 0.2704 (3) | 0.39484 (15) | 0.0475 (9) | 0.828 (5) |
C1 | 0.2847 (4) | 0.3833 (3) | 0.19853 (13) | 0.0269 (7) | |
C2 | 0.1960 (4) | 0.3174 (3) | 0.25545 (13) | 0.0283 (7) | |
C3 | 0.3033 (5) | 0.3765 (3) | 0.31058 (13) | 0.0308 (7) | |
C4 | 0.4957 (5) | 0.4176 (3) | 0.28620 (15) | 0.0415 (9) | |
C5 | 0.4951 (5) | 0.3941 (3) | 0.21707 (15) | 0.0381 (8) | |
C6 | 0.2535 (5) | 0.3130 (3) | 0.13903 (15) | 0.0333 (7) | |
C7 | 0.2012 (6) | 0.5084 (3) | 0.19023 (17) | 0.0474 (10) | |
C8 | 0.3332 (6) | 0.2938 (4) | 0.36514 (19) | 0.0358 (10) | 0.828 (5) |
C9 | −0.0188 (5) | 0.3317 (4) | 0.26240 (17) | 0.0464 (10) | |
C10 | 0.2418 (5) | 0.1839 (3) | 0.25171 (15) | 0.0397 (9) | |
N1 | 0.2817 (5) | −0.0891 (2) | −0.02925 (13) | 0.0485 (12) | 0.828 (5) |
N2 | 0.3063 (4) | 0.0882 (2) | 0.04047 (12) | 0.0340 (9) | 0.828 (5) |
C11 | 0.4843 (5) | −0.0666 (3) | −0.01434 (18) | 0.0528 (13) | 0.828 (5) |
C12 | 0.1761 (6) | −0.1121 (4) | 0.02843 (15) | 0.0505 (13) | 0.828 (5) |
C13 | 0.2009 (6) | 0.0173 (3) | −0.05952 (16) | 0.0520 (14) | 0.828 (5) |
C21 | 0.4991 (5) | 0.0488 (3) | 0.02227 (19) | 0.0534 (13) | 0.828 (5) |
C22 | 0.2074 (6) | −0.0090 (3) | 0.07306 (17) | 0.0437 (13) | 0.828 (5) |
C23 | 0.1974 (6) | 0.1221 (3) | −0.01484 (15) | 0.0477 (12) | 0.828 (5) |
N11 | 0.212 (2) | −0.0840 (13) | −0.0311 (7) | 0.069 (4)* | 0.172 (5) |
N12 | 0.209 (2) | 0.0933 (13) | 0.0393 (7) | 0.069 (4)* | 0.172 (5) |
C31 | 0.285 (3) | −0.114 (2) | 0.0306 (9) | 0.069 (4)* | 0.172 (5) |
C32 | 0.013 (2) | −0.0415 (18) | −0.0260 (10) | 0.069 (4)* | 0.172 (5) |
C33 | 0.331 (3) | 0.0108 (19) | −0.0582 (9) | 0.069 (4)* | 0.172 (5) |
C41 | 0.276 (4) | −0.010 (2) | 0.0754 (10) | 0.069 (4)* | 0.172 (5) |
C42 | 0.016 (2) | 0.0681 (18) | 0.0154 (10) | 0.069 (4)* | 0.172 (5) |
C43 | 0.340 (3) | 0.114 (2) | −0.0127 (9) | 0.069 (4)* | 0.172 (5) |
O5 | 0.7727 (4) | 0.1588 (2) | 0.12549 (15) | 0.0622 (9) | |
O13 | 0.098 (2) | 0.3170 (15) | 0.3928 (7) | 0.040* | 0.172 (5) |
O14 | 0.383 (2) | 0.2359 (14) | 0.3803 (8) | 0.040* | 0.172 (5) |
C58 | 0.247 (2) | 0.309 (2) | 0.3669 (8) | 0.040* | 0.172 (5) |
H3 | 0.2296 | 0.4476 | 0.3245 | 0.037* | |
H4 | 0.1958 | 0.2171 | 0.4210 | 0.071* | 0.828 (5) |
H4A | 0.5999 | 0.3728 | 0.3062 | 0.050* | |
H4B | 0.5142 | 0.5033 | 0.2945 | 0.050* | |
H5A | 0.5643 | 0.3197 | 0.2076 | 0.046* | |
H5B | 0.5565 | 0.4605 | 0.1948 | 0.046* | |
H7A | 0.2733 | 0.5510 | 0.1587 | 0.071* | |
H7B | 0.2093 | 0.5519 | 0.2291 | 0.071* | |
H7C | 0.0678 | 0.5022 | 0.1776 | 0.071* | |
H9A | −0.0826 | 0.2993 | 0.2261 | 0.070* | |
H9B | −0.0501 | 0.4161 | 0.2666 | 0.070* | |
H9C | −0.0617 | 0.2886 | 0.2989 | 0.070* | |
H10A | 0.1937 | 0.1438 | 0.2885 | 0.060* | |
H10B | 0.3799 | 0.1729 | 0.2490 | 0.060* | |
H10C | 0.1812 | 0.1498 | 0.2153 | 0.060* | |
H2 | 0.3164 | 0.1537 | 0.0663 | 0.041* | 0.828 (5) |
H11A | 0.5594 | −0.0599 | −0.0526 | 0.063* | 0.828 (5) |
H11B | 0.5360 | −0.1334 | 0.0100 | 0.063* | 0.828 (5) |
H12A | 0.2212 | −0.1871 | 0.0471 | 0.061* | 0.828 (5) |
H12B | 0.0387 | −0.1205 | 0.0195 | 0.061* | 0.828 (5) |
H13A | 0.0701 | −0.0001 | −0.0737 | 0.062* | 0.828 (5) |
H13B | 0.2788 | 0.0381 | −0.0958 | 0.062* | 0.828 (5) |
H21A | 0.5780 | 0.0358 | 0.0593 | 0.064* | 0.828 (5) |
H21B | 0.5608 | 0.1109 | −0.0030 | 0.064* | 0.828 (5) |
H22A | 0.0835 | 0.0196 | 0.0888 | 0.052* | 0.828 (5) |
H22B | 0.2850 | −0.0360 | 0.1083 | 0.052* | 0.828 (5) |
H23A | 0.2551 | 0.1930 | −0.0342 | 0.057* | 0.828 (5) |
H23B | 0.0645 | 0.1414 | −0.0036 | 0.057* | 0.828 (5) |
H12 | 0.2050 | 0.1604 | 0.0641 | 0.083* | 0.172 (5) |
H31A | 0.4186 | −0.1411 | 0.0269 | 0.083* | 0.172 (5) |
H31B | 0.2096 | −0.1809 | 0.0474 | 0.083* | 0.172 (5) |
H32A | −0.0682 | −0.1042 | −0.0080 | 0.083* | 0.172 (5) |
H32B | −0.0372 | −0.0207 | −0.0669 | 0.083* | 0.172 (5) |
H33A | 0.2759 | 0.0379 | −0.0975 | 0.083* | 0.172 (5) |
H33B | 0.4611 | −0.0196 | −0.0662 | 0.083* | 0.172 (5) |
H41A | 0.1874 | −0.0272 | 0.1094 | 0.083* | 0.172 (5) |
H41B | 0.4038 | 0.0065 | 0.0928 | 0.083* | 0.172 (5) |
H42A | −0.0305 | 0.1378 | −0.0080 | 0.083* | 0.172 (5) |
H42B | −0.0722 | 0.0553 | 0.0503 | 0.083* | 0.172 (5) |
H43A | 0.4713 | 0.1229 | 0.0028 | 0.083* | 0.172 (5) |
H43B | 0.3043 | 0.1889 | −0.0338 | 0.083* | 0.172 (5) |
H51 | 0.6662 | 0.2032 | 0.1249 | 0.080* | |
H52 | 0.8660 | 0.2135 | 0.1255 | 0.080* | |
H14 | 0.3474 | 0.1880 | 0.4074 | 0.060* | 0.172 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0421 (14) | 0.0547 (16) | 0.0423 (14) | 0.0034 (13) | −0.0005 (12) | −0.0213 (13) |
O2 | 0.0422 (14) | 0.0657 (18) | 0.0408 (14) | −0.0020 (14) | −0.0115 (12) | −0.0076 (14) |
O3 | 0.049 (2) | 0.061 (2) | 0.049 (2) | 0.006 (2) | −0.0076 (18) | 0.0141 (17) |
O4 | 0.0484 (19) | 0.050 (2) | 0.0441 (18) | −0.0012 (16) | 0.0120 (16) | 0.0184 (16) |
C1 | 0.0276 (16) | 0.0262 (15) | 0.0268 (15) | 0.0002 (13) | 0.0047 (13) | −0.0010 (13) |
C2 | 0.0302 (16) | 0.0257 (15) | 0.0290 (16) | −0.0006 (14) | 0.0043 (14) | −0.0010 (14) |
C3 | 0.0391 (17) | 0.0265 (15) | 0.0270 (16) | −0.0021 (15) | 0.0057 (15) | −0.0020 (13) |
C4 | 0.038 (2) | 0.055 (2) | 0.0312 (18) | −0.0118 (18) | 0.0041 (16) | −0.0039 (17) |
C5 | 0.0333 (19) | 0.049 (2) | 0.0322 (18) | −0.0134 (17) | 0.0026 (15) | −0.0060 (17) |
C6 | 0.0389 (18) | 0.0310 (16) | 0.0301 (16) | −0.0049 (15) | −0.0013 (15) | 0.0020 (14) |
C7 | 0.069 (3) | 0.0340 (18) | 0.039 (2) | 0.005 (2) | −0.002 (2) | 0.0043 (16) |
C8 | 0.045 (3) | 0.029 (2) | 0.033 (2) | −0.008 (2) | 0.010 (2) | −0.0040 (19) |
C9 | 0.0304 (18) | 0.060 (2) | 0.049 (2) | 0.0017 (18) | 0.0077 (16) | −0.0029 (19) |
C10 | 0.056 (2) | 0.0251 (16) | 0.0381 (18) | −0.0068 (15) | 0.0001 (18) | 0.0002 (15) |
N1 | 0.095 (3) | 0.0265 (18) | 0.0245 (18) | −0.013 (2) | −0.002 (2) | −0.0022 (15) |
N2 | 0.050 (2) | 0.0267 (17) | 0.0253 (17) | 0.0009 (17) | −0.0017 (17) | −0.0048 (14) |
C11 | 0.071 (3) | 0.044 (3) | 0.044 (3) | 0.004 (2) | 0.012 (2) | −0.004 (2) |
C12 | 0.075 (3) | 0.037 (2) | 0.039 (2) | −0.015 (3) | 0.004 (3) | 0.003 (2) |
C13 | 0.086 (4) | 0.042 (3) | 0.027 (2) | −0.010 (3) | −0.015 (2) | 0.0007 (19) |
C21 | 0.050 (3) | 0.051 (3) | 0.059 (3) | −0.001 (2) | 0.002 (2) | −0.017 (2) |
C22 | 0.066 (4) | 0.038 (2) | 0.027 (2) | −0.001 (3) | 0.001 (2) | −0.0021 (18) |
C23 | 0.074 (3) | 0.039 (2) | 0.030 (2) | 0.008 (2) | −0.016 (2) | 0.0041 (19) |
O5 | 0.0615 (18) | 0.0398 (15) | 0.085 (2) | −0.0043 (14) | −0.0098 (16) | −0.0021 (14) |
Geometric parameters (Å, º) top
O1—C6 | 1.273 (4) | C12—C22 | 1.530 (4) |
O2—C6 | 1.251 (4) | C12—H12A | 0.99 |
O3—C8 | 1.222 (5) | C12—H12B | 0.99 |
O4—C8 | 1.317 (5) | C13—C23 | 1.530 (4) |
O4—H4 | 0.84 | C13—H13A | 0.99 |
C1—C6 | 1.535 (4) | C13—H13B | 0.99 |
C1—C7 | 1.536 (4) | C21—H21A | 0.99 |
C1—C5 | 1.538 (4) | C21—H21B | 0.99 |
C1—C2 | 1.575 (4) | C22—H22A | 0.99 |
C2—C9 | 1.526 (5) | C22—H22B | 0.99 |
C2—C10 | 1.539 (4) | C23—H23A | 0.99 |
C2—C3 | 1.567 (4) | C23—H23B | 0.99 |
C3—C8 | 1.526 (5) | N11—C33 | 1.481 (3) |
C3—C4 | 1.526 (5) | N11—C32 | 1.481 (3) |
C3—H3 | 1.00 | N11—C31 | 1.481 (3) |
C4—C5 | 1.531 (4) | N12—C42 | 1.481 (3) |
C4—H4A | 0.99 | N12—C43 | 1.481 (3) |
C4—H4B | 0.99 | N12—C41 | 1.481 (3) |
C5—H5A | 0.99 | N12—H12 | 0.93 |
C5—H5B | 0.99 | C31—C41 | 1.529 (4) |
C7—H7A | 0.98 | C31—H31A | 0.99 |
C7—H7B | 0.98 | C31—H31B | 0.99 |
C7—H7C | 0.98 | C32—C42 | 1.529 (4) |
C9—H9A | 0.98 | C32—H32A | 0.99 |
C9—H9B | 0.98 | C32—H32B | 0.99 |
C9—H9C | 0.98 | C33—C43 | 1.529 (4) |
C10—H10A | 0.98 | C33—H33A | 0.99 |
C10—H10B | 0.98 | C33—H33B | 0.99 |
C10—H10C | 0.98 | C41—H41A | 0.99 |
N1—C13 | 1.480 (3) | C41—H41B | 0.99 |
N1—C11 | 1.483 (3) | C42—H42A | 0.99 |
N1—C12 | 1.484 (3) | C42—H42B | 0.99 |
N2—C22 | 1.479 (3) | C43—H43A | 0.99 |
N2—C23 | 1.479 (3) | C43—H43B | 0.99 |
N2—C21 | 1.481 (3) | O5—H51 | 0.90 |
N2—H2 | 0.93 | O5—H52 | 0.90 |
C11—C21 | 1.528 (4) | O13—C58 | 1.194 (10) |
C11—H11A | 0.99 | O14—C58 | 1.300 (10) |
C11—H11B | 0.99 | O14—H14 | 0.84 |
| | | |
C8—O3—H14 | 72.3 | N2—C21—C11 | 109.4 (2) |
C8—O4—H4 | 109.0 | N2—C21—H21A | 109.8 |
C6—C1—C7 | 108.5 (3) | C11—C21—H21A | 109.8 |
C6—C1—C5 | 113.6 (3) | N2—C21—H21B | 109.8 |
C7—C1—C5 | 109.0 (3) | C11—C21—H21B | 109.8 |
C6—C1—C2 | 111.6 (2) | H21A—C21—H21B | 108.2 |
C7—C1—C2 | 111.9 (3) | N2—C22—C12 | 108.8 (2) |
C5—C1—C2 | 102.2 (2) | N2—C22—H22A | 109.9 |
C9—C2—C10 | 108.4 (3) | C12—C22—H22A | 109.9 |
C9—C2—C3 | 110.8 (3) | N2—C22—H22B | 109.9 |
C10—C2—C3 | 110.7 (3) | C12—C22—H22B | 109.9 |
C9—C2—C1 | 114.9 (3) | H22A—C22—H22B | 108.3 |
C10—C2—C1 | 109.5 (2) | N2—C23—C13 | 108.2 (2) |
C3—C2—C1 | 102.4 (2) | N2—C23—H23A | 110.1 |
C8—C3—C4 | 109.5 (3) | C13—C23—H23A | 110.1 |
C8—C3—C2 | 114.0 (3) | N2—C23—H23B | 110.1 |
C4—C3—C2 | 106.7 (2) | C13—C23—H23B | 110.1 |
C8—C3—H3 | 108.8 | H23A—C23—H23B | 108.4 |
C4—C3—H3 | 108.8 | C33—N11—C32 | 109.4 (3) |
C2—C3—H3 | 108.8 | C33—N11—C31 | 109.3 (3) |
C3—C4—C5 | 106.7 (3) | C32—N11—C31 | 109.4 (3) |
C3—C4—H4A | 110.4 | C42—N12—C43 | 109.4 (3) |
C5—C4—H4A | 110.4 | C42—N12—C41 | 109.4 (3) |
C3—C4—H4B | 110.4 | C43—N12—C41 | 109.4 (3) |
C5—C4—H4B | 110.4 | C42—N12—H12 | 109.5 |
H4A—C4—H4B | 108.6 | C43—N12—H12 | 109.5 |
C4—C5—C1 | 106.0 (3) | C41—N12—H12 | 109.5 |
C4—C5—H5A | 110.5 | N11—C31—C41 | 113.0 (13) |
C1—C5—H5A | 110.5 | N11—C31—H31A | 109.0 |
C4—C5—H5B | 110.5 | C41—C31—H31A | 109.0 |
C1—C5—H5B | 110.5 | N11—C31—H31B | 109.0 |
H5A—C5—H5B | 108.7 | C41—C31—H31B | 109.0 |
O2—C6—O1 | 122.5 (3) | H31A—C31—H31B | 107.8 |
O2—C6—C1 | 119.1 (3) | N11—C32—C42 | 107.2 (12) |
O1—C6—C1 | 118.4 (3) | N11—C32—H32A | 110.3 |
O3—C8—O4 | 121.8 (4) | C42—C32—H32A | 110.3 |
O3—C8—C3 | 125.3 (3) | N11—C32—H32B | 110.3 |
O4—C8—C3 | 112.9 (3) | C42—C32—H32B | 110.3 |
O3—C8—H14 | 57.2 | H32A—C32—H32B | 108.5 |
O4—C8—H14 | 66.3 | N11—C33—C43 | 108.1 (12) |
C3—C8—H14 | 165.3 | N11—C33—H33A | 110.1 |
C13—N1—C11 | 109.17 (19) | C43—C33—H33A | 110.1 |
C13—N1—C12 | 109.12 (19) | N11—C33—H33B | 110.1 |
C11—N1—C12 | 108.94 (19) | C43—C33—H33B | 110.1 |
C22—N2—C23 | 109.82 (19) | H33A—C33—H33B | 108.4 |
C22—N2—C21 | 109.75 (19) | N12—C41—C31 | 105.9 (13) |
C23—N2—C21 | 109.43 (19) | N12—C41—H41A | 110.6 |
C22—N2—H2 | 109.3 | C31—C41—H41A | 110.6 |
C23—N2—H2 | 109.3 | N12—C41—H41B | 110.6 |
C21—N2—H2 | 109.3 | C31—C41—H41B | 110.6 |
N1—C11—C21 | 109.0 (2) | H41A—C41—H41B | 108.7 |
N1—C11—H11A | 109.9 | N12—C42—C32 | 111.8 (12) |
C21—C11—H11A | 109.9 | N12—C42—H42A | 109.3 |
N1—C11—H11B | 109.9 | C32—C42—H42A | 109.3 |
C21—C11—H11B | 109.9 | N12—C42—H42B | 109.3 |
H11A—C11—H11B | 108.3 | C32—C42—H42B | 109.3 |
N1—C12—C22 | 109.6 (2) | H42A—C42—H42B | 107.9 |
N1—C12—H12A | 109.8 | N12—C43—C33 | 110.6 (12) |
C22—C12—H12A | 109.8 | N12—C43—H43A | 109.5 |
N1—C12—H12B | 109.8 | C33—C43—H43A | 109.5 |
C22—C12—H12B | 109.8 | N12—C43—H43B | 109.5 |
H12A—C12—H12B | 108.2 | C33—C43—H43B | 109.5 |
N1—C13—C23 | 110.2 (2) | H43A—C43—H43B | 108.1 |
N1—C13—H13A | 109.6 | H51—O5—H52 | 103.1 |
C23—C13—H13A | 109.6 | C58—O13—H4 | 74.2 |
N1—C13—H13B | 109.6 | C58—O14—H14 | 110.3 |
C23—C13—H13B | 109.6 | O13—C58—O14 | 126.0 (14) |
H13A—C13—H13B | 108.1 | | |
| | | |
C6—C1—C2—C9 | −79.2 (3) | C13—N1—C11—C21 | 53.3 (4) |
C7—C1—C2—C9 | 42.6 (4) | C12—N1—C11—C21 | −65.8 (4) |
C5—C1—C2—C9 | 159.1 (3) | C13—N1—C12—C22 | −64.5 (3) |
C6—C1—C2—C10 | 43.0 (3) | C11—N1—C12—C22 | 54.6 (3) |
C7—C1—C2—C10 | 164.9 (3) | C11—N1—C13—C23 | −65.4 (4) |
C5—C1—C2—C10 | −78.7 (3) | C12—N1—C13—C23 | 53.5 (4) |
C6—C1—C2—C3 | 160.6 (3) | C22—N2—C21—C11 | 54.0 (4) |
C7—C1—C2—C3 | −77.6 (3) | C23—N2—C21—C11 | −66.6 (4) |
C5—C1—C2—C3 | 38.8 (3) | N1—C11—C21—N2 | 10.2 (4) |
C9—C2—C3—C8 | 88.5 (4) | C23—N2—C22—C12 | 55.2 (3) |
C10—C2—C3—C8 | −31.7 (4) | C21—N2—C22—C12 | −65.1 (3) |
C1—C2—C3—C8 | −148.4 (3) | N1—C12—C22—N2 | 9.1 (4) |
C9—C2—C3—C4 | −150.4 (3) | C22—N2—C23—C13 | −66.1 (4) |
C10—C2—C3—C4 | 89.4 (3) | C21—N2—C23—C13 | 54.4 (4) |
C1—C2—C3—C4 | −27.3 (3) | N1—C13—C23—N2 | 9.7 (4) |
C8—C3—C4—C5 | 128.9 (3) | C33—N11—C31—C41 | 62.1 (18) |
C2—C3—C4—C5 | 5.1 (4) | C32—N11—C31—C41 | −57.7 (18) |
C3—C4—C5—C1 | 20.1 (4) | C33—N11—C32—C42 | −60.0 (17) |
C6—C1—C5—C4 | −157.1 (3) | C31—N11—C32—C42 | 59.7 (17) |
C7—C1—C5—C4 | 81.7 (3) | C32—N11—C33—C43 | 66.1 (18) |
C2—C1—C5—C4 | −36.8 (3) | C31—N11—C33—C43 | −53.6 (18) |
C7—C1—C6—O2 | −51.2 (4) | C42—N12—C41—C31 | 62.0 (17) |
C5—C1—C6—O2 | −172.6 (3) | C43—N12—C41—C31 | −57.8 (17) |
C2—C1—C6—O2 | 72.5 (4) | N11—C31—C41—N12 | −4 (2) |
C7—C1—C6—O1 | 130.5 (3) | C43—N12—C42—C32 | 59.7 (18) |
C5—C1—C6—O1 | 9.1 (4) | C41—N12—C42—C32 | −60.1 (17) |
C2—C1—C6—O1 | −105.8 (3) | N11—C32—C42—N12 | −3 (2) |
C4—C3—C8—O3 | −12.0 (6) | C42—N12—C43—C33 | −53.5 (18) |
C2—C3—C8—O3 | 107.5 (5) | C41—N12—C43—C33 | 66.3 (18) |
C4—C3—C8—O4 | 169.4 (3) | N11—C33—C43—N12 | −7 (2) |
C2—C3—C8—O4 | −71.1 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.93 | 1.69 | 2.598 (4) | 165 |
O4—H4···N1i | 0.84 | 1.81 | 2.646 (4) | 172 |
O5—H51···O1 | 0.90 | 2.02 | 2.894 (4) | 164 |
O5—H52···O2ii | 0.90 | 1.92 | 2.810 (4) | 169 |
C23—H23A···O5iii | 0.99 | 2.60 | 3.491 (4) | 150 |
O14—H14···N11i | 0.84 | 1.83 | 2.67 (2) | 176 |
N12—H12···O2 | 0.93 | 2.18 | 3.066 (13) | 160 |
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, −z. |
(V) (1
R,3S)-Camphoric acid–hexamethylenetetramine (2/1)
top
Crystal data top
2(C10H16O4)·C6H12N4 | F(000) = 584 |
Mr = 540.65 | Dx = 1.256 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 1866 reflections |
a = 19.9172 (8) Å | θ = 2.8–27.4° |
b = 6.7515 (3) Å | µ = 0.09 mm−1 |
c = 10.6272 (4) Å | T = 150 K |
V = 1429.05 (10) Å3 | Block, colourless |
Z = 2 | 0.34 × 0.32 × 0.30 mm |
Data collection top
Kappa-CCD diffractometer | 1651 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.039 |
Graphite monochromator | θmax = 27.4°, θmin = 2.8° |
φ scans, and ω scans with κ offsets | h = 0→25 |
5749 measured reflections | k = 0→8 |
1866 independent reflections | l = 0→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-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 reflections | Δρmax = 0.18 e Å−3 |
179 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (6) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.62577 (7) | 0.9186 (2) | −0.50960 (12) | 0.0400 (4) | |
O2 | 0.62733 (7) | 1.2289 (2) | −0.43812 (13) | 0.0374 (3) | |
O3 | 0.65546 (7) | 0.57514 (19) | 0.01536 (12) | 0.0343 (3) | |
O4 | 0.61878 (7) | 0.87170 (19) | 0.07562 (12) | 0.0352 (3) | |
C11 | 0.68604 (8) | 0.9935 (3) | −0.31603 (15) | 0.0230 (4) | |
C12 | 0.63932 (8) | 0.9680 (3) | −0.19689 (15) | 0.0225 (4) | |
C13 | 0.68919 (8) | 0.8636 (3) | −0.10426 (15) | 0.0229 (4) | |
C14 | 0.73503 (9) | 0.7327 (3) | −0.18549 (16) | 0.0298 (4) | |
C15 | 0.72182 (9) | 0.7929 (3) | −0.32362 (16) | 0.0299 (4) | |
C16 | 0.64384 (8) | 1.0388 (3) | −0.43182 (16) | 0.0265 (4) | |
C17 | 0.73782 (9) | 1.1590 (3) | −0.29821 (18) | 0.0305 (4) | |
C18 | 0.65359 (8) | 0.7524 (3) | −0.00040 (16) | 0.0254 (4) | |
C19 | 0.61184 (10) | 1.1622 (3) | −0.14505 (18) | 0.0332 (4) | |
C110 | 0.58050 (9) | 0.8275 (3) | −0.22665 (18) | 0.0326 (4) | |
N1 | 0.53977 (7) | 0.6366 (2) | 0.22287 (14) | 0.0247 (3) | |
N2 | 0.54616 (7) | 0.3815 (2) | 0.38512 (13) | 0.0244 (3) | |
C1 | 0.58487 (8) | 0.5177 (3) | 0.30423 (17) | 0.0254 (4) | |
C2 | 0.49408 (9) | 0.7492 (3) | 0.30460 (16) | 0.0259 (4) | |
C3 | 0.5000 | 0.5000 | 0.1446 (2) | 0.0272 (5) | |
C4 | 0.5000 | 0.5000 | 0.4635 (2) | 0.0274 (5) | |
H2 | 0.6026 | 1.2479 | −0.5009 | 0.056* | |
H4 | 0.5951 | 0.8032 | 0.1244 | 0.053* | |
H13 | 0.7176 | 0.9683 | −0.0644 | 0.027* | |
H14A | 0.7243 | 0.5910 | −0.1725 | 0.036* | |
H14B | 0.7827 | 0.7548 | −0.1633 | 0.036* | |
H15A | 0.7646 | 0.8050 | −0.3705 | 0.036* | |
H15B | 0.6931 | 0.6936 | −0.3661 | 0.036* | |
H17A | 0.7657 | 1.1696 | −0.3739 | 0.046* | |
H17B | 0.7663 | 1.1284 | −0.2256 | 0.046* | |
H17C | 0.7146 | 1.2848 | −0.2838 | 0.046* | |
H19A | 0.5870 | 1.2316 | −0.2113 | 0.050* | |
H19B | 0.6491 | 1.2454 | −0.1163 | 0.050* | |
H19C | 0.5817 | 1.1346 | −0.0742 | 0.050* | |
H11A | 0.5540 | 0.8055 | −0.1503 | 0.049* | |
H11B | 0.5981 | 0.7006 | −0.2570 | 0.049* | |
H11C | 0.5520 | 0.8869 | −0.2916 | 0.049* | |
H1A | 0.6161 | 0.4403 | 0.2509 | 0.030* | |
H1B | 0.6119 | 0.6075 | 0.3576 | 0.030* | |
H2A | 0.5206 | 0.8402 | 0.3581 | 0.031* | |
H2B | 0.4637 | 0.8304 | 0.2519 | 0.031* | |
H3A | 0.5305 | 0.4227 | 0.0898 | 0.033* | 0.50 |
H3B | 0.4695 | 0.5773 | 0.0898 | 0.033* | 0.50 |
H4A | 0.5264 | 0.5895 | 0.5183 | 0.033* | 0.50 |
H4B | 0.4736 | 0.4105 | 0.5183 | 0.033* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0498 (8) | 0.0401 (8) | 0.0300 (7) | −0.0015 (7) | −0.0140 (7) | −0.0056 (6) |
O2 | 0.0465 (8) | 0.0335 (7) | 0.0322 (7) | 0.0078 (6) | −0.0176 (6) | 0.0025 (6) |
O3 | 0.0428 (8) | 0.0249 (7) | 0.0354 (7) | −0.0005 (6) | 0.0041 (6) | 0.0066 (5) |
O4 | 0.0454 (8) | 0.0275 (7) | 0.0325 (7) | −0.0031 (6) | 0.0166 (6) | 0.0035 (6) |
C11 | 0.0225 (7) | 0.0255 (9) | 0.0210 (7) | 0.0010 (7) | −0.0012 (6) | 0.0016 (7) |
C12 | 0.0204 (7) | 0.0234 (9) | 0.0236 (8) | 0.0011 (6) | −0.0010 (6) | 0.0008 (7) |
C13 | 0.0226 (7) | 0.0234 (9) | 0.0227 (8) | −0.0007 (7) | −0.0007 (6) | 0.0025 (7) |
C14 | 0.0291 (8) | 0.0308 (10) | 0.0296 (9) | 0.0082 (8) | 0.0027 (7) | 0.0050 (8) |
C15 | 0.0302 (8) | 0.0339 (10) | 0.0255 (9) | 0.0085 (8) | 0.0014 (7) | 0.0002 (8) |
C16 | 0.0240 (8) | 0.0314 (10) | 0.0240 (8) | −0.0009 (7) | −0.0020 (7) | 0.0018 (8) |
C17 | 0.0254 (8) | 0.0376 (10) | 0.0285 (8) | −0.0067 (8) | −0.0040 (7) | 0.0064 (8) |
C18 | 0.0258 (8) | 0.0257 (9) | 0.0246 (8) | −0.0026 (7) | −0.0009 (7) | 0.0009 (7) |
C19 | 0.0390 (9) | 0.0298 (10) | 0.0308 (9) | 0.0095 (8) | 0.0056 (8) | −0.0008 (8) |
C110 | 0.0236 (8) | 0.0394 (11) | 0.0348 (10) | −0.0044 (8) | −0.0038 (8) | 0.0018 (9) |
N1 | 0.0259 (7) | 0.0232 (7) | 0.0250 (7) | −0.0019 (6) | 0.0024 (6) | 0.0034 (6) |
N2 | 0.0242 (7) | 0.0243 (8) | 0.0249 (7) | 0.0018 (6) | −0.0016 (6) | 0.0026 (6) |
C1 | 0.0199 (7) | 0.0262 (9) | 0.0301 (8) | −0.0004 (7) | −0.0004 (7) | 0.0010 (8) |
C2 | 0.0284 (8) | 0.0184 (8) | 0.0307 (8) | −0.0005 (7) | 0.0010 (8) | −0.0002 (8) |
C3 | 0.0322 (12) | 0.0310 (14) | 0.0185 (10) | −0.0023 (11) | 0.000 | 0.000 |
C4 | 0.0320 (12) | 0.0322 (14) | 0.0179 (11) | 0.0009 (11) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
O1—C16 | 1.213 (2) | C17—H17B | 0.98 |
O2—C16 | 1.327 (2) | C17—H17C | 0.98 |
O2—H2 | 0.84 | C19—H19A | 0.98 |
O3—C18 | 1.209 (2) | C19—H19B | 0.98 |
O4—C18 | 1.335 (2) | C19—H19C | 0.98 |
O4—H4 | 0.84 | C110—H11A | 0.98 |
C11—C16 | 1.521 (2) | C110—H11B | 0.98 |
C11—C15 | 1.532 (3) | C110—H11C | 0.98 |
C11—C17 | 1.533 (2) | N1—C2 | 1.470 (2) |
C11—C12 | 1.581 (2) | N1—C3 | 1.473 (2) |
C12—C19 | 1.524 (2) | N1—C1 | 1.483 (2) |
C12—C110 | 1.540 (2) | N2—C2i | 1.468 (2) |
C12—C13 | 1.566 (2) | N2—C1 | 1.476 (2) |
C13—C18 | 1.511 (2) | N2—C4 | 1.4764 (19) |
C13—C14 | 1.537 (2) | C1—H1A | 0.99 |
C13—H13 | 1.00 | C1—H1B | 0.99 |
C14—C15 | 1.546 (2) | C2—H2A | 0.99 |
C14—H14A | 0.99 | C2—H2B | 0.99 |
C14—H14B | 0.99 | C3—H3A | 0.99 |
C15—H15A | 0.99 | C3—H3B | 0.99 |
C15—H15B | 0.99 | C4—H4A | 0.99 |
C17—H17A | 0.98 | C4—H4B | 0.99 |
| | | |
C16—O2—H2 | 109.5 | O4—C18—C13 | 112.70 (15) |
C18—O4—H4 | 109.5 | C12—C19—H19A | 109.5 |
C16—C11—C15 | 113.10 (15) | C12—C19—H19B | 109.5 |
C16—C11—C17 | 108.96 (14) | H19A—C19—H19B | 109.5 |
C15—C11—C17 | 109.75 (14) | C12—C19—H19C | 109.5 |
C16—C11—C12 | 110.15 (13) | H19A—C19—H19C | 109.5 |
C15—C11—C12 | 102.70 (14) | H19B—C19—H19C | 109.5 |
C17—C11—C12 | 112.12 (14) | C12—C110—H11A | 109.5 |
C19—C12—C110 | 109.33 (14) | C12—C110—H11B | 109.5 |
C19—C12—C13 | 112.82 (14) | H11A—C110—H11B | 109.5 |
C110—C12—C13 | 109.53 (14) | C12—C110—H11C | 109.5 |
C19—C12—C11 | 114.04 (14) | H11A—C110—H11C | 109.5 |
C110—C12—C11 | 110.50 (14) | H11B—C110—H11C | 109.5 |
C13—C12—C11 | 100.32 (12) | C2—N1—C3 | 108.95 (12) |
C18—C13—C14 | 113.78 (14) | C2—N1—C1 | 108.09 (13) |
C18—C13—C12 | 112.65 (13) | C3—N1—C1 | 108.41 (12) |
C14—C13—C12 | 106.42 (13) | C2i—N2—C1 | 108.68 (14) |
C18—C13—H13 | 107.9 | C2i—N2—C4 | 108.36 (11) |
C14—C13—H13 | 107.9 | C1—N2—C4 | 108.46 (12) |
C12—C13—H13 | 107.9 | N2—C1—N1 | 111.13 (12) |
C13—C14—C15 | 106.32 (14) | N2—C1—H1A | 109.4 |
C13—C14—H14A | 110.5 | N1—C1—H1A | 109.4 |
C15—C14—H14A | 110.5 | N2—C1—H1B | 109.4 |
C13—C14—H14B | 110.5 | N1—C1—H1B | 109.4 |
C15—C14—H14B | 110.5 | H1A—C1—H1B | 108.0 |
H14A—C14—H14B | 108.7 | N2i—C2—N1 | 111.81 (13) |
C11—C15—C14 | 105.17 (14) | N2i—C2—H2A | 109.3 |
C11—C15—H15A | 110.7 | N1—C2—H2A | 109.3 |
C14—C15—H15A | 110.7 | N2i—C2—H2B | 109.3 |
C11—C15—H15B | 110.7 | N1—C2—H2B | 109.3 |
C14—C15—H15B | 110.7 | H2A—C2—H2B | 107.9 |
H15A—C15—H15B | 108.8 | N1—C3—N1i | 111.24 (19) |
O1—C16—O2 | 122.64 (16) | N1—C3—H3A | 109.4 |
O1—C16—C11 | 125.47 (17) | N1i—C3—H3A | 109.4 |
O2—C16—C11 | 111.87 (15) | N1—C3—H3B | 109.4 |
C11—C17—H17A | 109.5 | N1i—C3—H3B | 109.4 |
C11—C17—H17B | 109.5 | H3A—C3—H3B | 108.0 |
H17A—C17—H17B | 109.5 | N2—C4—N2i | 111.26 (18) |
C11—C17—H17C | 109.5 | N2—C4—H4A | 109.4 |
H17A—C17—H17C | 109.5 | N2i—C4—H4A | 109.4 |
H17B—C17—H17C | 109.5 | N2—C4—H4B | 109.4 |
O3—C18—O4 | 121.96 (16) | N2i—C4—H4B | 109.4 |
O3—C18—C13 | 125.33 (16) | H4A—C4—H4B | 108.0 |
| | | |
C16—C11—C12—C19 | −75.15 (19) | C15—C11—C16—O1 | 16.9 (2) |
C15—C11—C12—C19 | 164.11 (14) | C17—C11—C16—O1 | 139.22 (18) |
C17—C11—C12—C19 | 46.37 (19) | C12—C11—C16—O1 | −97.4 (2) |
C16—C11—C12—C110 | 48.5 (2) | C15—C11—C16—O2 | −164.22 (15) |
C15—C11—C12—C110 | −72.27 (16) | C17—C11—C16—O2 | −41.9 (2) |
C17—C11—C12—C110 | 170.00 (14) | C12—C11—C16—O2 | 81.51 (18) |
C16—C11—C12—C13 | 164.00 (14) | C14—C13—C18—O3 | −5.3 (2) |
C15—C11—C12—C13 | 43.26 (16) | C12—C13—C18—O3 | 115.95 (19) |
C17—C11—C12—C13 | −74.48 (17) | C14—C13—C18—O4 | 174.45 (14) |
C19—C12—C13—C18 | 79.55 (18) | C12—C13—C18—O4 | −64.31 (19) |
C110—C12—C13—C18 | −42.48 (19) | C2i—N2—C1—N1 | 58.60 (17) |
C11—C12—C13—C18 | −158.73 (14) | C4—N2—C1—N1 | −59.00 (17) |
C19—C12—C13—C14 | −155.11 (14) | C2—N1—C1—N2 | 58.94 (18) |
C110—C12—C13—C14 | 82.86 (16) | C3—N1—C1—N2 | −59.01 (17) |
C11—C12—C13—C14 | −33.39 (16) | C3—N1—C2—N2i | 58.28 (17) |
C18—C13—C14—C15 | 135.93 (15) | C1—N1—C2—N2i | −59.32 (17) |
C12—C13—C14—C15 | 11.28 (18) | C2—N1—C3—N1i | −58.52 (10) |
C16—C11—C15—C14 | −156.23 (14) | C1—N1—C3—N1i | 58.89 (9) |
C17—C11—C15—C14 | 81.86 (17) | C2i—N2—C4—N2i | −58.85 (10) |
C12—C11—C15—C14 | −37.54 (17) | C1—N2—C4—N2i | 58.97 (10) |
C13—C14—C15—C11 | 16.52 (19) | | |
Symmetry code: (i) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N2ii | 0.84 | 1.88 | 2.684 (2) | 159 |
O4—H4···N1 | 0.84 | 1.89 | 2.728 (2) | 175 |
Symmetry code: (ii) x, y+1, z−1. |
(VI) (1
R,3S)-Camphoric acid–piperazine (1/1)
top
Crystal data top
C10H14O4·C4H12N2 | F(000) = 624 |
Mr = 286.37 | Dx = 1.228 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 1776 reflections |
a = 19.1277 (4) Å | θ = 2.9–26.0° |
b = 7.5743 (6) Å | µ = 0.09 mm−1 |
c = 10.6920 (12) Å | T = 150 K |
V = 1549.0 (2) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.30 × 0.28 mm |
Data collection top
Kappa-CCD diffractometer | 1373 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.057 |
Graphite monochromator | θmax = 26.0°, θmin = 2.9° |
φ scans, and ω scans with κ offsets | h = 0→23 |
6537 measured reflections | k = 0→9 |
1776 independent reflections | l = 0→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-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 reflections | Δρmax = 0.18 e Å−3 |
266 parameters | Δρmin = −0.17 e Å−3 |
50 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.036 (5) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.2362 (2) | 0.3589 (5) | 0.3404 (4) | 0.0335 (10) | |
N4 | 0.2633 (2) | 0.6309 (5) | 0.1617 (4) | 0.0356 (11) | |
C2 | 0.1978 (3) | 0.5316 (6) | 0.3450 (5) | 0.0411 (13) | |
C3 | 0.2434 (3) | 0.6771 (7) | 0.2918 (6) | 0.0409 (13) | |
C5 | 0.3004 (2) | 0.4618 (6) | 0.1533 (5) | 0.0355 (12) | |
C6 | 0.2567 (3) | 0.3163 (6) | 0.2103 (6) | 0.0364 (12) | |
O11 | −0.1439 (10) | 0.167 (2) | 0.527 (2) | 0.042 (2) | 0.50 |
O12 | −0.1821 (8) | −0.066 (3) | 0.433 (3) | 0.0358 (17) | 0.50 |
O13 | 0.1405 (9) | −0.159 (2) | 0.547 (2) | 0.042 (2) | 0.50 |
O14 | 0.1767 (8) | 0.094 (3) | 0.460 (3) | 0.0358 (17) | 0.50 |
C11 | −0.0610 (6) | −0.0192 (12) | 0.3984 (8) | 0.034 (2) | 0.50 |
C12 | 0.0043 (5) | 0.0509 (8) | 0.4667 (7) | 0.025 (2) | 0.50 |
C13 | 0.0632 (6) | −0.0542 (11) | 0.4017 (10) | 0.034 (2) | 0.50 |
C14 | 0.0330 (6) | −0.2422 (11) | 0.3880 (15) | 0.056 (4) | 0.50 |
C15 | −0.0474 (6) | −0.2198 (11) | 0.3869 (15) | 0.050 (3) | 0.50 |
C16 | −0.1304 (7) | 0.032 (3) | 0.461 (2) | 0.0397 (16) | 0.50 |
C17 | −0.0726 (5) | 0.0463 (16) | 0.2631 (8) | 0.054 (3) | 0.50 |
C18 | 0.1338 (9) | −0.034 (3) | 0.469 (2) | 0.0397 (16) | 0.50 |
C19 | 0.0138 (7) | 0.2503 (10) | 0.4486 (13) | 0.049 (3) | 0.50 |
C110 | −0.0009 (19) | −0.012 (5) | 0.6046 (7) | 0.043 (3) | 0.50 |
O21 | 0.6687 (7) | 1.1183 (18) | 0.0342 (16) | 0.0436 (18) | 0.50 |
O22 | 0.6456 (4) | 0.8406 (11) | −0.0144 (12) | 0.026 (2) | 0.50 |
O23 | 0.3211 (7) | 0.924 (2) | 0.0629 (16) | 0.0436 (18) | 0.50 |
O24 | 0.3570 (4) | 1.1564 (11) | −0.0504 (11) | 0.026 (2) | 0.50 |
C21 | 0.5608 (6) | 0.9749 (15) | 0.1126 (11) | 0.031 (5) | 0.50 |
C22 | 0.5017 (5) | 1.0712 (10) | 0.0412 (8) | 0.031 (2) | 0.50 |
C23 | 0.4338 (6) | 1.0033 (17) | 0.1039 (13) | 0.031 (5) | 0.50 |
C24 | 0.4509 (5) | 0.8085 (14) | 0.1349 (17) | 0.068 (4) | 0.50 |
C25 | 0.5312 (5) | 0.7878 (13) | 0.1302 (12) | 0.044 (3) | 0.50 |
C26 | 0.6312 (9) | 0.981 (2) | 0.043 (3) | 0.0263 (13) | 0.50 |
C27 | 0.5742 (5) | 1.0573 (17) | 0.2416 (9) | 0.062 (3) | 0.50 |
C28 | 0.3663 (9) | 1.036 (3) | 0.029 (2) | 0.0263 (13) | 0.50 |
C29 | 0.5095 (7) | 1.2719 (10) | 0.0434 (12) | 0.050 (3) | 0.50 |
C210 | 0.500 (2) | 1.022 (5) | −0.0988 (7) | 0.039 (6) | 0.50 |
H1A | 0.2754 | 0.3653 | 0.3899 | 0.040* | |
H1B | 0.2080 | 0.2707 | 0.3713 | 0.040* | |
H4A | 0.2236 | 0.6254 | 0.1134 | 0.043* | |
H4B | 0.2913 | 0.7187 | 0.1298 | 0.043* | |
H2A | 0.1853 | 0.5598 | 0.4326 | 0.049* | |
H2B | 0.1541 | 0.5228 | 0.2959 | 0.049* | |
H3A | 0.2176 | 0.7904 | 0.2926 | 0.049* | |
H3B | 0.2860 | 0.6909 | 0.3437 | 0.049* | |
H5A | 0.3456 | 0.4704 | 0.1979 | 0.043* | |
H5B | 0.3102 | 0.4340 | 0.0645 | 0.043* | |
H6A | 0.2142 | 0.2985 | 0.1591 | 0.044* | |
H6B | 0.2837 | 0.2048 | 0.2097 | 0.044* | |
H13 | 0.0688 | −0.0046 | 0.3155 | 0.041* | 0.50 |
H14A | 0.0477 | −0.3174 | 0.4590 | 0.068* | 0.50 |
H14B | 0.0492 | −0.2973 | 0.3092 | 0.068* | 0.50 |
H15A | −0.0674 | −0.2661 | 0.3081 | 0.060* | 0.50 |
H15B | −0.0688 | −0.2839 | 0.4580 | 0.060* | 0.50 |
H17A | −0.0310 | 0.0206 | 0.2128 | 0.082* | 0.50 |
H17B | −0.0810 | 0.1740 | 0.2638 | 0.082* | 0.50 |
H17C | −0.1131 | −0.0140 | 0.2269 | 0.082* | 0.50 |
H19A | 0.0556 | 0.2896 | 0.4938 | 0.074* | 0.50 |
H19B | −0.0273 | 0.3125 | 0.4812 | 0.074* | 0.50 |
H19C | 0.0192 | 0.2763 | 0.3594 | 0.074* | 0.50 |
H11A | −0.0069 | −0.1405 | 0.6066 | 0.064* | 0.50 |
H11B | −0.0411 | 0.0446 | 0.6449 | 0.064* | 0.50 |
H11C | 0.0420 | 0.0201 | 0.6492 | 0.064* | 0.50 |
H23 | 0.4288 | 1.0673 | 0.1852 | 0.038* | 0.50 |
H24A | 0.4332 | 0.7781 | 0.2192 | 0.082* | 0.50 |
H24B | 0.4285 | 0.7291 | 0.0732 | 0.082* | 0.50 |
H25A | 0.5487 | 0.7351 | 0.2089 | 0.053* | 0.50 |
H25B | 0.5450 | 0.7109 | 0.0595 | 0.053* | 0.50 |
H27A | 0.5932 | 1.1766 | 0.2311 | 0.093* | 0.50 |
H27B | 0.6078 | 0.9846 | 0.2877 | 0.093* | 0.50 |
H27C | 0.5302 | 1.0634 | 0.2883 | 0.093* | 0.50 |
H9A | 0.5107 | 1.3131 | 0.1302 | 0.075* | 0.50 |
H9B | 0.4697 | 1.3259 | 0.0002 | 0.075* | 0.50 |
H9C | 0.5529 | 1.3055 | 0.0011 | 0.075* | 0.50 |
H21A | 0.4953 | 0.8943 | −0.1076 | 0.058* | 0.50 |
H21B | 0.5436 | 1.0611 | −0.1386 | 0.058* | 0.50 |
H21C | 0.4603 | 1.0811 | −0.1390 | 0.058* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.026 (2) | 0.036 (2) | 0.039 (3) | −0.0021 (18) | 0.000 (2) | 0.001 (2) |
N4 | 0.032 (2) | 0.036 (2) | 0.039 (3) | −0.0023 (19) | −0.003 (2) | 0.003 (2) |
C2 | 0.041 (3) | 0.048 (3) | 0.034 (3) | 0.003 (2) | 0.005 (3) | −0.003 (3) |
C3 | 0.035 (3) | 0.042 (3) | 0.046 (3) | 0.004 (3) | −0.002 (3) | −0.002 (3) |
C5 | 0.024 (2) | 0.033 (2) | 0.050 (3) | 0.004 (2) | 0.004 (2) | −0.005 (3) |
C6 | 0.041 (3) | 0.029 (2) | 0.040 (3) | 0.000 (2) | 0.005 (3) | −0.009 (2) |
O11 | 0.034 (2) | 0.041 (2) | 0.052 (6) | −0.0034 (18) | 0.001 (5) | 0.010 (6) |
O12 | 0.040 (3) | 0.037 (6) | 0.030 (9) | −0.001 (3) | 0.008 (3) | −0.001 (3) |
O13 | 0.034 (2) | 0.041 (2) | 0.052 (6) | −0.0034 (18) | 0.001 (5) | 0.010 (6) |
O14 | 0.040 (3) | 0.037 (6) | 0.030 (9) | −0.001 (3) | 0.008 (3) | −0.001 (3) |
C11 | 0.027 (3) | 0.042 (7) | 0.034 (3) | 0.017 (5) | 0.009 (4) | 0.001 (3) |
C12 | 0.025 (4) | 0.025 (5) | 0.026 (4) | −0.004 (5) | 0.000 (5) | 0.003 (4) |
C13 | 0.027 (3) | 0.042 (7) | 0.034 (3) | 0.017 (5) | 0.009 (4) | 0.001 (3) |
C14 | 0.029 (6) | 0.038 (6) | 0.101 (11) | 0.003 (5) | −0.027 (7) | −0.029 (7) |
C15 | 0.040 (7) | 0.029 (5) | 0.081 (9) | 0.016 (5) | −0.008 (6) | −0.016 (6) |
C16 | 0.041 (3) | 0.050 (3) | 0.028 (4) | 0.004 (3) | −0.020 (8) | 0.006 (11) |
C17 | 0.039 (5) | 0.090 (8) | 0.034 (5) | 0.013 (6) | 0.015 (4) | 0.009 (6) |
C18 | 0.041 (3) | 0.050 (3) | 0.028 (4) | 0.004 (3) | −0.020 (8) | 0.006 (11) |
C19 | 0.030 (7) | 0.027 (5) | 0.090 (10) | 0.002 (4) | 0.013 (7) | 0.004 (7) |
C110 | 0.030 (4) | 0.064 (8) | 0.035 (5) | 0.005 (6) | −0.022 (10) | −0.009 (12) |
O21 | 0.040 (4) | 0.043 (6) | 0.047 (6) | −0.010 (4) | 0.006 (3) | −0.007 (3) |
O22 | 0.0309 (18) | 0.0374 (18) | 0.009 (7) | 0.0021 (15) | 0.003 (2) | −0.002 (2) |
O23 | 0.040 (4) | 0.043 (6) | 0.047 (6) | −0.010 (4) | 0.006 (3) | −0.007 (3) |
O24 | 0.0309 (18) | 0.0374 (18) | 0.009 (7) | 0.0021 (15) | 0.003 (2) | −0.002 (2) |
C21 | 0.020 (8) | 0.042 (8) | 0.032 (10) | 0.003 (6) | 0.009 (7) | 0.001 (8) |
C22 | 0.028 (4) | 0.025 (4) | 0.040 (5) | 0.006 (4) | −0.006 (5) | 0.002 (4) |
C23 | 0.032 (10) | 0.038 (8) | 0.025 (9) | −0.009 (7) | 0.004 (7) | 0.007 (7) |
C24 | 0.031 (6) | 0.049 (6) | 0.123 (13) | −0.001 (5) | 0.011 (7) | 0.038 (8) |
C25 | 0.031 (5) | 0.049 (5) | 0.053 (7) | 0.013 (5) | 0.000 (5) | 0.021 (5) |
C26 | 0.016 (2) | 0.033 (4) | 0.030 (5) | −0.002 (2) | 0.002 (6) | 0.000 (7) |
C27 | 0.042 (5) | 0.102 (10) | 0.041 (6) | 0.024 (6) | −0.021 (5) | −0.001 (6) |
C28 | 0.016 (2) | 0.033 (4) | 0.030 (5) | −0.002 (2) | 0.002 (6) | 0.000 (7) |
C29 | 0.051 (7) | 0.024 (4) | 0.075 (8) | −0.010 (5) | 0.002 (7) | 0.005 (6) |
C210 | 0.044 (5) | 0.042 (18) | 0.029 (4) | 0.002 (9) | 0.011 (9) | 0.003 (6) |
Geometric parameters (Å, º) top
N1—C6 | 1.481 (7) | C17—H17A | 0.98 |
N1—C2 | 1.500 (6) | C17—H17B | 0.98 |
N1—H1A | 0.92 | C17—H17C | 0.98 |
N1—H1B | 0.92 | C19—H19A | 0.98 |
N4—C5 | 1.467 (5) | C19—H19B | 0.98 |
N4—C3 | 1.484 (7) | C19—H19C | 0.98 |
N4—H4A | 0.92 | C110—H11A | 0.98 |
N4—H4B | 0.92 | C110—H11B | 0.98 |
C2—C3 | 1.516 (7) | C110—H11C | 0.98 |
C2—H2A | 0.99 | O21—C26 | 1.264 (7) |
C2—H2B | 0.99 | O22—C26 | 1.260 (7) |
C3—H3A | 0.99 | O23—C28 | 1.265 (7) |
C3—H3B | 0.99 | O24—C28 | 1.255 (7) |
C5—C6 | 1.512 (6) | C21—C27 | 1.536 (10) |
C5—H5A | 0.99 | C21—C25 | 1.538 (10) |
C5—H5B | 0.99 | C21—C26 | 1.540 (8) |
C6—H6A | 0.99 | C21—C22 | 1.546 (9) |
C6—H6B | 0.99 | C22—C29 | 1.527 (8) |
O11—C16 | 1.274 (7) | C22—C210 | 1.542 (9) |
O12—C16 | 1.271 (7) | C22—C23 | 1.549 (9) |
O13—C18 | 1.273 (7) | C23—C28 | 1.542 (8) |
O14—C18 | 1.272 (7) | C23—C24 | 1.547 (9) |
C11—C16 | 1.534 (8) | C23—H23 | 1.00 |
C11—C12 | 1.541 (9) | C24—C25 | 1.544 (8) |
C11—C15 | 1.546 (8) | C24—H24A | 0.99 |
C11—C17 | 1.546 (9) | C24—H24B | 0.99 |
C12—C19 | 1.534 (8) | C25—H25A | 0.99 |
C12—C13 | 1.545 (8) | C25—H25B | 0.99 |
C12—C110 | 1.552 (10) | C27—H27A | 0.98 |
C13—C18 | 1.536 (8) | C27—H27B | 0.98 |
C13—C14 | 1.544 (9) | C27—H27C | 0.98 |
C13—H13 | 1.00 | C29—H9A | 0.98 |
C14—C15 | 1.547 (8) | C29—H9B | 0.98 |
C14—H14A | 0.99 | C29—H9C | 0.98 |
C14—H14B | 0.99 | C210—H21A | 0.98 |
C15—H15A | 0.99 | C210—H21B | 0.98 |
C15—H15B | 0.99 | C210—H21C | 0.98 |
| | | |
C6—N1—C2 | 110.5 (4) | C11—C17—H17C | 109.5 |
C6—N1—H1A | 109.5 | H17A—C17—H17C | 109.5 |
C2—N1—H1A | 109.5 | H17B—C17—H17C | 109.5 |
C6—N1—H1B | 109.5 | O14—C18—O13 | 123 (2) |
C2—N1—H1B | 109.5 | O14—C18—C13 | 127.5 (16) |
H1A—N1—H1B | 108.1 | O13—C18—C13 | 108.7 (16) |
C5—N4—C3 | 112.8 (4) | C12—C19—H19A | 109.5 |
C5—N4—H4A | 109.0 | C12—C19—H19B | 109.5 |
C3—N4—H4A | 109.0 | H19A—C19—H19B | 109.5 |
C5—N4—H4B | 109.0 | C12—C19—H19C | 109.5 |
C3—N4—H4B | 109.0 | H19A—C19—H19C | 109.5 |
H4A—N4—H4B | 107.8 | H19B—C19—H19C | 109.5 |
N1—C2—C3 | 109.9 (4) | C12—C110—H11A | 109.5 |
N1—C2—H2A | 109.7 | C12—C110—H11B | 109.5 |
C3—C2—H2A | 109.7 | H11A—C110—H11B | 109.5 |
N1—C2—H2B | 109.7 | C12—C110—H11C | 109.5 |
C3—C2—H2B | 109.7 | H11A—C110—H11C | 109.5 |
H2A—C2—H2B | 108.2 | H11B—C110—H11C | 109.5 |
N4—C3—C2 | 109.1 (4) | C27—C21—C25 | 109.0 (11) |
N4—C3—H3A | 109.9 | C27—C21—C26 | 106.0 (12) |
C2—C3—H3A | 109.9 | C25—C21—C26 | 114.3 (9) |
N4—C3—H3B | 109.9 | C27—C21—C22 | 111.9 (8) |
C2—C3—H3B | 109.9 | C25—C21—C22 | 103.1 (7) |
H3A—C3—H3B | 108.3 | C26—C21—C22 | 112.6 (15) |
N4—C5—C6 | 110.1 (4) | C29—C22—C210 | 104.8 (17) |
N4—C5—H5A | 109.6 | C29—C22—C21 | 113.1 (9) |
C6—C5—H5A | 109.6 | C210—C22—C21 | 112.4 (18) |
N4—C5—H5B | 109.6 | C29—C22—C23 | 113.9 (9) |
C6—C5—H5B | 109.6 | C210—C22—C23 | 108.8 (17) |
H5A—C5—H5B | 108.2 | C21—C22—C23 | 104.0 (6) |
N1—C6—C5 | 111.5 (4) | C28—C23—C24 | 116.2 (12) |
N1—C6—H6A | 109.3 | C28—C23—C22 | 115.0 (11) |
C5—C6—H6A | 109.3 | C24—C23—C22 | 103.4 (8) |
N1—C6—H6B | 109.3 | C28—C23—H23 | 107.2 |
C5—C6—H6B | 109.3 | C24—C23—H23 | 107.2 |
H6A—C6—H6B | 108.0 | C22—C23—H23 | 107.2 |
C16—C11—C12 | 114.1 (9) | C25—C24—C23 | 107.4 (8) |
C16—C11—C15 | 115.4 (12) | C25—C24—H24A | 110.2 |
C12—C11—C15 | 103.9 (7) | C23—C24—H24A | 110.2 |
C16—C11—C17 | 101.6 (13) | C25—C24—H24B | 110.2 |
C12—C11—C17 | 116.7 (9) | C23—C24—H24B | 110.2 |
C15—C11—C17 | 105.4 (9) | H24A—C24—H24B | 108.5 |
C19—C12—C11 | 112.1 (9) | C21—C25—C24 | 106.1 (9) |
C19—C12—C13 | 111.3 (8) | C21—C25—H25A | 110.5 |
C11—C12—C13 | 101.5 (6) | C24—C25—H25A | 110.5 |
C19—C12—C110 | 115.5 (18) | C21—C25—H25B | 110.5 |
C11—C12—C110 | 107.0 (12) | C24—C25—H25B | 110.5 |
C13—C12—C110 | 108.4 (17) | H25A—C25—H25B | 108.7 |
C18—C13—C14 | 117.8 (10) | O22—C26—O21 | 122.4 (15) |
C18—C13—C12 | 112.3 (14) | O22—C26—C21 | 113.5 (10) |
C14—C13—C12 | 104.2 (8) | O21—C26—C21 | 123.9 (13) |
C18—C13—H13 | 107.4 | C21—C27—H27A | 109.5 |
C14—C13—H13 | 107.4 | C21—C27—H27B | 109.5 |
C12—C13—H13 | 107.4 | H27A—C27—H27B | 109.5 |
C13—C14—C15 | 105.8 (8) | C21—C27—H27C | 109.5 |
C13—C14—H14A | 110.6 | H27A—C27—H27C | 109.5 |
C15—C14—H14A | 110.6 | H27B—C27—H27C | 109.5 |
C13—C14—H14B | 110.6 | O24—C28—O23 | 125.7 (16) |
C15—C14—H14B | 110.6 | O24—C28—C23 | 125.9 (10) |
H14A—C14—H14B | 108.7 | O23—C28—C23 | 108.3 (12) |
C11—C15—C14 | 105.9 (9) | C22—C29—H9A | 109.5 |
C11—C15—H15A | 110.6 | C22—C29—H9B | 109.5 |
C14—C15—H15A | 110.6 | H9A—C29—H9B | 109.5 |
C11—C15—H15B | 110.6 | C22—C29—H9C | 109.5 |
C14—C15—H15B | 110.6 | H9A—C29—H9C | 109.5 |
H15A—C15—H15B | 108.7 | H9B—C29—H9C | 109.5 |
O12—C16—O11 | 116 (2) | C22—C210—H21A | 109.5 |
O12—C16—C11 | 115.2 (15) | C22—C210—H21B | 109.5 |
O11—C16—C11 | 128.4 (16) | H21A—C210—H21B | 109.5 |
C11—C17—H17A | 109.5 | C22—C210—H21C | 109.5 |
C11—C17—H17B | 109.5 | H21A—C210—H21C | 109.5 |
H17A—C17—H17B | 109.5 | H21B—C210—H21C | 109.5 |
| | | |
C6—N1—C2—C3 | −58.1 (5) | C12—C13—C18—O14 | −81 (3) |
C5—N4—C3—C2 | −58.2 (5) | C14—C13—C18—O13 | −28 (3) |
N1—C2—C3—N4 | 57.9 (5) | C12—C13—C18—O13 | 93 (2) |
C3—N4—C5—C6 | 56.3 (5) | C27—C21—C22—C29 | 47.2 (13) |
C2—N1—C6—C5 | 56.5 (5) | C25—C21—C22—C29 | 164.2 (10) |
N4—C5—C6—N1 | −54.9 (6) | C26—C21—C22—C29 | −72.2 (13) |
C16—C11—C12—C19 | −73.1 (15) | C27—C21—C22—C210 | 165.5 (17) |
C15—C11—C12—C19 | 160.4 (10) | C25—C21—C22—C210 | −77.5 (18) |
C17—C11—C12—C19 | 44.9 (12) | C26—C21—C22—C210 | 46.2 (17) |
C16—C11—C12—C13 | 168.0 (13) | C27—C21—C22—C23 | −76.9 (13) |
C15—C11—C12—C13 | 41.5 (10) | C25—C21—C22—C23 | 40.1 (10) |
C17—C11—C12—C13 | −74.0 (9) | C26—C21—C22—C23 | 163.8 (9) |
C16—C11—C12—C110 | 54 (2) | C29—C22—C23—C28 | 73.0 (19) |
C15—C11—C12—C110 | −72.1 (19) | C210—C22—C23—C28 | −43 (2) |
C17—C11—C12—C110 | 172.5 (18) | C21—C22—C23—C28 | −163.4 (15) |
C19—C12—C13—C18 | 70.9 (13) | C29—C22—C23—C24 | −159.2 (11) |
C11—C12—C13—C18 | −169.7 (10) | C210—C22—C23—C24 | 84 (2) |
C110—C12—C13—C18 | −57.2 (15) | C21—C22—C23—C24 | −35.7 (12) |
C19—C12—C13—C14 | −160.6 (10) | C28—C23—C24—C25 | 144.8 (17) |
C11—C12—C13—C14 | −41.2 (9) | C22—C23—C24—C25 | 17.8 (17) |
C110—C12—C13—C14 | 71.3 (15) | C27—C21—C25—C24 | 90.3 (13) |
C18—C13—C14—C15 | 150.2 (17) | C26—C21—C25—C24 | −151.3 (17) |
C12—C13—C14—C15 | 25.2 (14) | C22—C21—C25—C24 | −28.7 (14) |
C16—C11—C15—C14 | −152.0 (15) | C23—C24—C25—C21 | 6.8 (19) |
C12—C11—C15—C14 | −26.3 (14) | C27—C21—C26—O22 | 136 (2) |
C17—C11—C15—C14 | 96.9 (13) | C25—C21—C26—O22 | 16 (3) |
C13—C14—C15—C11 | 0.7 (17) | C22—C21—C26—O22 | −101 (2) |
C12—C11—C16—O12 | −158.4 (16) | C27—C21—C26—O21 | −50 (3) |
C15—C11—C16—O12 | −38 (3) | C25—C21—C26—O21 | −170 (2) |
C17—C11—C16—O12 | 75 (2) | C22—C21—C26—O21 | 73 (3) |
C12—C11—C16—O11 | 28 (3) | C24—C23—C28—O24 | −147 (2) |
C15—C11—C16—O11 | 148 (2) | C22—C23—C28—O24 | −26 (4) |
C17—C11—C16—O11 | −98 (3) | C24—C23—C28—O23 | 35 (3) |
C14—C13—C18—O14 | 158 (2) | C22—C23—C28—O23 | 156.5 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O11i | 0.92 | 1.80 | 2.70 (2) | 168 |
N1—H1A···O13ii | 0.92 | 1.75 | 2.65 (2) | 165 |
N1—H1B···O12iii | 0.92 | 1.76 | 2.64 (2) | 160 |
N1—H1B···O14 | 0.92 | 1.75 | 2.64 (3) | 162 |
N4—H4A···O22iv | 0.92 | 1.85 | 2.756 (12) | 169 |
N4—H4A···O24v | 0.92 | 1.70 | 2.598 (11) | 165 |
N4—H4B···O21vi | 0.92 | 1.78 | 2.677 (14) | 165 |
N4—H4B···O23 | 0.92 | 1.81 | 2.698 (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) x−1/2, −y+3/2, −z; (v) −x+1/2, y−1/2, −z; (vi) −x+1, −y+2, z. |
(VII) (1
R,3S)-Camphoric acid–
N,
N'-dimethylpiperazine–water
(3/1/2)
top
Crystal data top
C10H16O4·2(C10H15O4)·(C6H16N2)·2H2O | F(000) = 816 |
Mr = 750.91 | Dx = 1.218 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 2095 reflections |
a = 13.5730 (4) Å | θ = 3.0–25.0° |
b = 22.0500 (8) Å | µ = 0.09 mm−1 |
c = 6.8417 (2) Å | T = 150 K |
V = 2047.62 (11) Å3 | Plate, colourless |
Z = 2 | 0.28 × 0.22 × 0.10 mm |
Data collection top
Kappa-CCD diffractometer | 1634 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.061 |
Graphite monochromator | θmax = 25.0°, θmin = 3.0° |
φ scans, and ω scans with κ offsets | h = 0→16 |
10832 measured reflections | k = 0→26 |
2095 independent reflections | l = 0→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-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 reflections | Δρmax = 0.17 e Å−3 |
279 parameters | Δρmin = −0.16 e Å−3 |
17 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.016 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O11 | 0.33237 (14) | 0.39238 (9) | 0.5336 (3) | 0.0391 (5) | |
O12 | 0.34266 (17) | 0.39076 (9) | 0.8532 (3) | 0.0472 (6) | |
O13 | 0.10923 (15) | 0.16156 (9) | 0.5115 (3) | 0.0399 (5) | |
O14 | 0.11203 (16) | 0.15307 (10) | 0.8359 (3) | 0.0453 (6) | |
C11 | 0.3414 (2) | 0.29374 (12) | 0.6922 (4) | 0.0327 (6) | |
C12 | 0.2407 (2) | 0.26648 (12) | 0.7631 (4) | 0.0326 (7) | |
C13 | 0.2500 (2) | 0.19960 (12) | 0.6895 (4) | 0.0340 (6) | |
C14 | 0.3101 (2) | 0.20236 (14) | 0.4985 (4) | 0.0456 (8) | |
C15 | 0.3521 (2) | 0.26696 (13) | 0.4854 (4) | 0.0400 (7) | |
C16 | 0.3382 (2) | 0.36310 (13) | 0.6930 (4) | 0.0345 (6) | |
C17 | 0.4296 (2) | 0.27338 (13) | 0.8176 (5) | 0.0433 (7) | |
C18 | 0.1510 (2) | 0.16958 (12) | 0.6659 (4) | 0.0345 (7) | |
C19 | 0.2248 (3) | 0.26972 (15) | 0.9846 (4) | 0.0487 (9) | |
C110 | 0.1542 (2) | 0.29837 (14) | 0.6618 (5) | 0.0414 (7) | |
O21 | −0.2376 (7) | 0.4890 (5) | 0.2495 (11) | 0.041 (2) | 0.50 |
O22 | −0.1798 (7) | 0.5865 (4) | 0.294 (3) | 0.0442 (19) | 0.50 |
O23 | 0.2567 (8) | 0.4967 (5) | 0.2308 (11) | 0.041 (2) | 0.50 |
O24 | 0.1732 (7) | 0.4181 (4) | 0.340 (3) | 0.0442 (19) | 0.50 |
C21 | −0.0795 (8) | 0.5121 (4) | 0.1174 (11) | 0.0336 (13) | 0.50 |
C22 | 0.0141 (5) | 0.5132 (3) | 0.2474 (6) | 0.0314 (18) | 0.50 |
C23 | 0.0892 (8) | 0.4780 (4) | 0.1182 (12) | 0.0336 (13) | 0.50 |
C24 | 0.0279 (4) | 0.4240 (3) | 0.0435 (12) | 0.0500 (18) | 0.50 |
C25 | −0.0789 (4) | 0.4474 (3) | 0.0275 (9) | 0.0418 (15) | 0.50 |
C26 | −0.1775 (7) | 0.5314 (4) | 0.210 (4) | 0.039 (3) | 0.50 |
C27 | −0.0768 (5) | 0.5591 (3) | −0.0496 (10) | 0.0455 (17) | 0.50 |
C28 | 0.1785 (7) | 0.4703 (5) | 0.247 (4) | 0.039 (3) | 0.50 |
C29 | 0.0528 (5) | 0.5769 (3) | 0.2942 (13) | 0.061 (2) | 0.50 |
C210 | −0.0077 (8) | 0.4807 (3) | 0.4411 (7) | 0.050 (3) | 0.50 |
N1 | 0.39397 (16) | 0.50789 (10) | 0.7269 (3) | 0.0317 (5) | |
C2 | 0.4539 (2) | 0.51920 (13) | 0.5473 (4) | 0.0340 (7) | |
C6 | 0.4541 (2) | 0.51950 (14) | 0.9034 (4) | 0.0413 (8) | |
C7 | 0.3028 (2) | 0.54518 (14) | 0.7305 (5) | 0.0417 (8) | |
O3 | 0.43824 (13) | 0.39526 (9) | 0.1984 (3) | 0.0380 (5) | |
H14 | 0.0552 | 0.1391 | 0.8173 | 0.068* | |
H13 | 0.2888 | 0.1761 | 0.7881 | 0.041* | |
H14A | 0.3642 | 0.1722 | 0.5013 | 0.055* | |
H14B | 0.2674 | 0.1937 | 0.3846 | 0.055* | |
H15A | 0.3145 | 0.2914 | 0.3894 | 0.048* | |
H15B | 0.4221 | 0.2660 | 0.4452 | 0.048* | |
H17A | 0.4328 | 0.2290 | 0.8194 | 0.065* | |
H17B | 0.4214 | 0.2885 | 0.9513 | 0.065* | |
H17C | 0.4906 | 0.2897 | 0.7619 | 0.065* | |
H19A | 0.2794 | 0.2493 | 1.0515 | 0.073* | |
H19B | 0.1627 | 0.2496 | 1.0184 | 0.073* | |
H19C | 0.2222 | 0.3123 | 1.0257 | 0.073* | |
H11A | 0.1654 | 0.2990 | 0.5204 | 0.062* | |
H11B | 0.1489 | 0.3401 | 0.7103 | 0.062* | |
H11C | 0.0931 | 0.2765 | 0.6901 | 0.062* | |
H22 | −0.2341 | 0.5914 | 0.3503 | 0.066* | 0.50 |
H24 | 0.2214 | 0.4147 | 0.4159 | 0.066* | 0.50 |
H23 | 0.1076 | 0.5041 | 0.0042 | 0.040* | 0.50 |
H24A | 0.0318 | 0.3896 | 0.1361 | 0.060* | 0.50 |
H24B | 0.0522 | 0.4103 | −0.0857 | 0.060* | 0.50 |
H25A | −0.1243 | 0.4204 | 0.1002 | 0.050* | 0.50 |
H25B | −0.0999 | 0.4487 | −0.1110 | 0.050* | 0.50 |
H27A | −0.0195 | 0.5513 | −0.1330 | 0.068* | 0.50 |
H27B | −0.0720 | 0.6000 | 0.0058 | 0.068* | 0.50 |
H27C | −0.1371 | 0.5558 | −0.1275 | 0.068* | 0.50 |
H29A | 0.0662 | 0.5986 | 0.1721 | 0.092* | 0.50 |
H29B | 0.1136 | 0.5736 | 0.3706 | 0.092* | 0.50 |
H29C | 0.0032 | 0.5991 | 0.3699 | 0.092* | 0.50 |
H21A | −0.0338 | 0.4401 | 0.4141 | 0.075* | 0.50 |
H21B | −0.0564 | 0.5040 | 0.5154 | 0.075* | 0.50 |
H21C | 0.0531 | 0.4772 | 0.5173 | 0.075* | 0.50 |
H1 | 0.3756 | 0.4673 | 0.7276 | 0.038* | |
H2A | 0.4722 | 0.5626 | 0.5412 | 0.041* | |
H2B | 0.4140 | 0.5096 | 0.4302 | 0.041* | |
H6A | 0.4146 | 0.5106 | 1.0216 | 0.050* | |
H6B | 0.4732 | 0.5628 | 0.9073 | 0.050* | |
H7A | 0.2639 | 0.5370 | 0.6127 | 0.063* | |
H7B | 0.3204 | 0.5883 | 0.7344 | 0.063* | |
H7C | 0.2639 | 0.5349 | 0.8465 | 0.063* | |
H31 | 0.4126 | 0.3887 | 0.3178 | 0.073* | |
H32 | 0.4004 | 0.3886 | 0.0924 | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O11 | 0.0374 (11) | 0.0382 (12) | 0.0417 (11) | 0.0003 (10) | 0.0017 (9) | 0.0109 (10) |
O12 | 0.0632 (14) | 0.0332 (12) | 0.0451 (13) | −0.0030 (11) | −0.0188 (11) | −0.0072 (10) |
O13 | 0.0482 (12) | 0.0387 (12) | 0.0328 (12) | −0.0079 (10) | −0.0016 (9) | −0.0041 (9) |
O14 | 0.0441 (13) | 0.0538 (14) | 0.0378 (12) | −0.0172 (11) | 0.0030 (10) | 0.0042 (10) |
C11 | 0.0345 (15) | 0.0286 (15) | 0.0351 (15) | −0.0060 (13) | −0.0048 (13) | 0.0011 (12) |
C12 | 0.0382 (16) | 0.0286 (15) | 0.0310 (15) | −0.0061 (13) | 0.0021 (12) | −0.0046 (12) |
C13 | 0.0370 (16) | 0.0281 (15) | 0.0369 (14) | −0.0033 (13) | 0.0031 (14) | −0.0038 (13) |
C14 | 0.051 (2) | 0.0402 (19) | 0.0454 (19) | −0.0058 (15) | 0.0143 (15) | −0.0107 (15) |
C15 | 0.0425 (17) | 0.0382 (17) | 0.0392 (17) | −0.0077 (15) | 0.0071 (13) | −0.0025 (14) |
C16 | 0.0268 (14) | 0.0348 (16) | 0.0418 (16) | −0.0052 (13) | −0.0055 (13) | 0.0027 (14) |
C17 | 0.0388 (17) | 0.0343 (16) | 0.0567 (19) | −0.0006 (14) | −0.0111 (15) | 0.0056 (15) |
C18 | 0.0438 (17) | 0.0252 (15) | 0.0345 (16) | 0.0014 (13) | 0.0021 (13) | −0.0014 (13) |
C19 | 0.061 (2) | 0.048 (2) | 0.0373 (17) | −0.0163 (17) | 0.0087 (15) | −0.0113 (15) |
C110 | 0.0317 (16) | 0.0351 (17) | 0.0575 (19) | 0.0004 (14) | 0.0018 (14) | −0.0050 (15) |
O21 | 0.015 (3) | 0.057 (5) | 0.0507 (17) | 0.006 (4) | 0.0059 (18) | 0.003 (2) |
O22 | 0.0340 (15) | 0.069 (2) | 0.029 (7) | −0.0017 (14) | −0.0003 (18) | 0.005 (2) |
O23 | 0.015 (3) | 0.057 (5) | 0.0507 (17) | 0.006 (4) | 0.0059 (18) | 0.003 (2) |
O24 | 0.0340 (15) | 0.069 (2) | 0.029 (7) | −0.0017 (14) | −0.0003 (18) | 0.005 (2) |
C21 | 0.026 (2) | 0.043 (3) | 0.0325 (15) | 0.004 (2) | 0.013 (4) | 0.006 (4) |
C22 | 0.019 (5) | 0.040 (6) | 0.035 (2) | −0.005 (3) | −0.004 (3) | −0.006 (3) |
C23 | 0.026 (2) | 0.043 (3) | 0.0325 (15) | 0.004 (2) | 0.013 (4) | 0.006 (4) |
C24 | 0.040 (4) | 0.052 (4) | 0.058 (4) | 0.013 (4) | −0.018 (4) | −0.019 (4) |
C25 | 0.034 (3) | 0.048 (4) | 0.043 (3) | 0.001 (3) | −0.003 (3) | −0.015 (3) |
C26 | 0.0354 (18) | 0.069 (2) | 0.013 (8) | −0.0038 (17) | −0.002 (3) | −0.001 (3) |
C27 | 0.036 (4) | 0.050 (4) | 0.051 (4) | 0.010 (3) | −0.001 (3) | 0.008 (3) |
C28 | 0.0354 (18) | 0.069 (2) | 0.013 (8) | −0.0038 (17) | −0.002 (3) | −0.001 (3) |
C29 | 0.044 (4) | 0.040 (4) | 0.099 (6) | −0.004 (3) | −0.016 (4) | −0.020 (4) |
C210 | 0.041 (4) | 0.082 (8) | 0.027 (2) | 0.010 (7) | −0.003 (3) | 0.003 (3) |
N1 | 0.0285 (12) | 0.0261 (12) | 0.0406 (13) | 0.0002 (10) | 0.0011 (10) | 0.0008 (10) |
C2 | 0.0326 (16) | 0.0421 (18) | 0.0273 (12) | 0.0061 (13) | −0.0001 (12) | 0.0030 (12) |
C6 | 0.0421 (19) | 0.053 (2) | 0.0285 (13) | 0.0095 (16) | 0.0001 (13) | −0.0014 (14) |
C7 | 0.0327 (16) | 0.0395 (18) | 0.0530 (18) | 0.0059 (14) | 0.0035 (14) | 0.0044 (15) |
O3 | 0.0366 (11) | 0.0452 (12) | 0.0321 (10) | 0.0002 (9) | −0.0042 (8) | 0.0023 (9) |
Geometric parameters (Å, º) top
O11—C16 | 1.270 (3) | C21—C22 | 1.551 (8) |
O12—C16 | 1.256 (3) | C21—C25 | 1.555 (9) |
O13—C18 | 1.212 (3) | C22—C29 | 1.534 (6) |
O14—C18 | 1.328 (3) | C22—C210 | 1.535 (6) |
O14—H14 | 0.84 | C22—C23 | 1.556 (8) |
C11—C16 | 1.530 (4) | C23—C28 | 1.511 (12) |
C11—C17 | 1.539 (4) | C23—C24 | 1.540 (8) |
C11—C15 | 1.540 (4) | C23—H23 | 1.00 |
C11—C12 | 1.570 (4) | C24—C25 | 1.542 (7) |
C12—C19 | 1.533 (4) | C24—H24A | 0.99 |
C12—C110 | 1.534 (4) | C24—H24B | 0.99 |
C12—C13 | 1.564 (4) | C25—H25A | 0.99 |
C13—C18 | 1.507 (4) | C25—H25B | 0.99 |
C13—C14 | 1.541 (4) | C27—H27A | 0.98 |
C13—H13 | 1.00 | C27—H27B | 0.98 |
C14—C15 | 1.537 (4) | C27—H27C | 0.98 |
C14—H14A | 0.99 | C29—H29A | 0.98 |
C14—H14B | 0.99 | C29—H29B | 0.98 |
C15—H15A | 0.99 | C29—H29C | 0.98 |
C15—H15B | 0.99 | C210—H21A | 0.98 |
C17—H17A | 0.98 | C210—H21B | 0.98 |
C17—H17B | 0.98 | C210—H21C | 0.98 |
C17—H17C | 0.98 | N1—C6 | 1.480 (3) |
C19—H19A | 0.98 | N1—C7 | 1.486 (3) |
C19—H19B | 0.98 | N1—C2 | 1.494 (3) |
C19—H19C | 0.98 | N1—H1 | 0.93 |
C110—H11A | 0.98 | C2—C2i | 1.512 (6) |
C110—H11B | 0.98 | C2—H2A | 0.99 |
C110—H11C | 0.98 | C2—H2B | 0.99 |
O21—C26 | 1.270 (11) | C6—C6i | 1.513 (6) |
O22—C26 | 1.343 (11) | C6—H6A | 0.99 |
O22—H22 | 0.84 | C6—H6B | 0.99 |
O23—C28 | 1.216 (11) | C7—H7A | 0.98 |
O24—C28 | 1.313 (11) | C7—H7B | 0.98 |
O24—H24 | 0.84 | C7—H7C | 0.98 |
C21—C26 | 1.534 (10) | O3—H31 | 0.90 |
C21—C27 | 1.542 (8) | O3—H32 | 0.90 |
| | | |
C18—O14—H14 | 109.5 | C28—C23—C24 | 122.7 (8) |
C16—C11—C17 | 108.2 (2) | C28—C23—C22 | 104.4 (9) |
C16—C11—C15 | 112.9 (2) | C24—C23—C22 | 102.7 (6) |
C17—C11—C15 | 109.1 (3) | C28—C23—H23 | 108.7 |
C16—C11—C12 | 110.9 (2) | C24—C23—H23 | 108.7 |
C17—C11—C12 | 113.1 (2) | C22—C23—H23 | 108.7 |
C15—C11—C12 | 102.6 (2) | C23—C24—C25 | 105.8 (6) |
C19—C12—C110 | 108.5 (3) | C23—C24—H24A | 110.6 |
C19—C12—C13 | 112.0 (2) | C25—C24—H24A | 110.6 |
C110—C12—C13 | 110.4 (2) | C23—C24—H24B | 110.6 |
C19—C12—C11 | 114.2 (2) | C25—C24—H24B | 110.6 |
C110—C12—C11 | 110.6 (2) | H24A—C24—H24B | 108.7 |
C13—C12—C11 | 101.0 (2) | C24—C25—C21 | 106.5 (6) |
C18—C13—C14 | 113.5 (2) | C24—C25—H25A | 110.4 |
C18—C13—C12 | 112.1 (2) | C21—C25—H25A | 110.4 |
C14—C13—C12 | 106.2 (2) | C24—C25—H25B | 110.4 |
C18—C13—H13 | 108.3 | C21—C25—H25B | 110.4 |
C14—C13—H13 | 108.3 | H25A—C25—H25B | 108.6 |
C12—C13—H13 | 108.3 | O21—C26—O22 | 124.1 (12) |
C15—C14—C13 | 106.4 (2) | O21—C26—C21 | 116.2 (10) |
C15—C14—H14A | 110.4 | O22—C26—C21 | 116.6 (10) |
C13—C14—H14A | 110.4 | C21—C27—H27A | 109.5 |
C15—C14—H14B | 110.4 | C21—C27—H27B | 109.5 |
C13—C14—H14B | 110.4 | H27A—C27—H27B | 109.5 |
H14A—C14—H14B | 108.6 | C21—C27—H27C | 109.5 |
C14—C15—C11 | 105.5 (2) | H27A—C27—H27C | 109.5 |
C14—C15—H15A | 110.6 | H27B—C27—H27C | 109.5 |
C11—C15—H15A | 110.6 | O23—C28—O24 | 120.9 (10) |
C14—C15—H15B | 110.6 | O23—C28—C23 | 126.2 (17) |
C11—C15—H15B | 110.6 | O24—C28—C23 | 109.6 (10) |
H15A—C15—H15B | 108.8 | C22—C29—H29A | 109.5 |
O12—C16—O11 | 120.4 (2) | C22—C29—H29B | 109.5 |
O12—C16—C11 | 119.2 (3) | H29A—C29—H29B | 109.5 |
O11—C16—C11 | 120.4 (3) | C22—C29—H29C | 109.5 |
C11—C17—H17A | 109.5 | H29A—C29—H29C | 109.5 |
C11—C17—H17B | 109.5 | H29B—C29—H29C | 109.5 |
H17A—C17—H17B | 109.5 | C22—C210—H21A | 109.5 |
C11—C17—H17C | 109.5 | C22—C210—H21B | 109.5 |
H17A—C17—H17C | 109.5 | H21A—C210—H21B | 109.5 |
H17B—C17—H17C | 109.5 | C22—C210—H21C | 109.5 |
O13—C18—O14 | 122.5 (3) | H21A—C210—H21C | 109.5 |
O13—C18—C13 | 125.1 (3) | H21B—C210—H21C | 109.5 |
O14—C18—C13 | 112.5 (2) | C6—N1—C7 | 110.5 (2) |
C12—C19—H19A | 109.5 | C6—N1—C2 | 110.0 (2) |
C12—C19—H19B | 109.5 | C7—N1—C2 | 112.0 (2) |
H19A—C19—H19B | 109.5 | C6—N1—H1 | 108.1 |
C12—C19—H19C | 109.5 | C7—N1—H1 | 108.1 |
H19A—C19—H19C | 109.5 | C2—N1—H1 | 108.1 |
H19B—C19—H19C | 109.5 | N1—C2—C2i | 110.93 (18) |
C12—C110—H11A | 109.5 | N1—C2—H2A | 109.5 |
C12—C110—H11B | 109.5 | C2i—C2—H2A | 109.5 |
H11A—C110—H11B | 109.5 | N1—C2—H2B | 109.5 |
C12—C110—H11C | 109.5 | C2i—C2—H2B | 109.5 |
H11A—C110—H11C | 109.5 | H2A—C2—H2B | 108.0 |
H11B—C110—H11C | 109.5 | N1—C6—C6i | 110.8 (2) |
C26—C21—C27 | 98.1 (10) | N1—C6—H6A | 109.5 |
C26—C21—C22 | 118.0 (10) | C6i—C6—H6A | 109.5 |
C27—C21—C22 | 113.3 (7) | N1—C6—H6B | 109.5 |
C26—C21—C25 | 115.0 (8) | C6i—C6—H6B | 109.5 |
C27—C21—C25 | 108.9 (6) | H6A—C6—H6B | 108.1 |
C22—C21—C25 | 103.7 (6) | N1—C7—H7A | 109.5 |
C29—C22—C210 | 108.2 (5) | N1—C7—H7B | 109.5 |
C29—C22—C21 | 114.4 (6) | H7A—C7—H7B | 109.5 |
C210—C22—C21 | 109.3 (6) | N1—C7—H7C | 109.5 |
C29—C22—C23 | 110.5 (5) | H7A—C7—H7C | 109.5 |
C210—C22—C23 | 112.6 (7) | H7B—C7—H7C | 109.5 |
C21—C22—C23 | 101.7 (4) | H31—O3—H32 | 119.0 |
| | | |
C16—C11—C12—C19 | −76.4 (3) | C25—C21—C22—C29 | 158.7 (6) |
C17—C11—C12—C19 | 45.4 (3) | C26—C21—C22—C210 | 48.7 (9) |
C15—C11—C12—C19 | 162.8 (2) | C27—C21—C22—C210 | 162.4 (7) |
C16—C11—C12—C110 | 46.4 (3) | C25—C21—C22—C210 | −79.7 (7) |
C17—C11—C12—C110 | 168.1 (2) | C26—C21—C22—C23 | 168.0 (6) |
C15—C11—C12—C110 | −74.5 (3) | C27—C21—C22—C23 | −78.3 (9) |
C16—C11—C12—C13 | 163.2 (2) | C25—C21—C22—C23 | 39.5 (7) |
C17—C11—C12—C13 | −75.0 (3) | C29—C22—C23—C28 | 65.1 (9) |
C15—C11—C12—C13 | 42.4 (3) | C210—C22—C23—C28 | −56.1 (8) |
C19—C12—C13—C18 | 80.6 (3) | C21—C22—C23—C28 | −172.9 (6) |
C110—C12—C13—C18 | −40.4 (3) | C29—C22—C23—C24 | −165.8 (6) |
C11—C12—C13—C18 | −157.4 (2) | C210—C22—C23—C24 | 73.0 (7) |
C19—C12—C13—C14 | −154.9 (3) | C21—C22—C23—C24 | −43.8 (7) |
C110—C12—C13—C14 | 84.1 (3) | C28—C23—C24—C25 | 148.0 (13) |
C11—C12—C13—C14 | −32.9 (3) | C22—C23—C24—C25 | 31.3 (8) |
C18—C13—C14—C15 | 134.7 (3) | C23—C24—C25—C21 | −6.8 (9) |
C12—C13—C14—C15 | 11.0 (3) | C26—C21—C25—C24 | −150.8 (12) |
C13—C14—C15—C11 | 16.1 (3) | C27—C21—C25—C24 | 100.3 (7) |
C16—C11—C15—C14 | −156.1 (2) | C22—C21—C25—C24 | −20.5 (7) |
C17—C11—C15—C14 | 83.5 (3) | C27—C21—C26—O21 | 132.8 (17) |
C12—C11—C15—C14 | −36.7 (3) | C22—C21—C26—O21 | −105.3 (18) |
C17—C11—C16—O12 | −49.9 (4) | C25—C21—C26—O21 | 18 (2) |
C15—C11—C16—O12 | −170.8 (3) | C27—C21—C26—O22 | −66.4 (16) |
C12—C11—C16—O12 | 74.7 (3) | C22—C21—C26—O22 | 55.5 (17) |
C17—C11—C16—O11 | 129.2 (3) | C25—C21—C26—O22 | 178.4 (11) |
C15—C11—C16—O11 | 8.3 (4) | C24—C23—C28—O23 | 136.4 (13) |
C12—C11—C16—O11 | −106.3 (3) | C22—C23—C28—O23 | −107.8 (18) |
C14—C13—C18—O13 | −17.8 (4) | C24—C23—C28—O24 | −23 (2) |
C12—C13—C18—O13 | 102.5 (3) | C22—C23—C28—O24 | 92.8 (13) |
C14—C13—C18—O14 | 163.2 (2) | C6—N1—C2—C2i | 56.6 (3) |
C12—C13—C18—O14 | −76.5 (3) | C7—N1—C2—C2i | 180.0 (3) |
C26—C21—C22—C29 | −72.8 (9) | C7—N1—C6—C6i | 178.6 (3) |
C27—C21—C22—C29 | 40.9 (8) | C2—N1—C6—C6i | −57.3 (3) |
Symmetry code: (i) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O11 | 0.93 | 2.20 | 2.989 (3) | 142 |
N1—H1···O12 | 0.93 | 1.95 | 2.811 (3) | 154 |
O3—H31···O11 | 0.90 | 1.84 | 2.708 (3) | 162 |
O3—H32···O12ii | 0.90 | 1.82 | 2.696 (3) | 166 |
O14—H14···O3iii | 0.84 | 1.76 | 2.599 (3) | 174 |
O22—H22···O11iv | 0.84 | 1.87 | 2.683 (18) | 164 |
O24—H24···O11 | 0.84 | 1.78 | 2.598 (17) | 165 |
Symmetry codes: (ii) x, y, z−1; (iii) x−1/2, −y+1/2, −z+1; (iv) −x, −y+1, z. |
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