Quininium (
R)-mandelate, C
20H
25N
2O

·C
8H
7O

, is an organic salt with an incommensurately modulated structure. The superspace approach is required for a precise description of the structure at room temperature. In addition to the main reflections, the diffraction pattern also exhibits higher-order satellite reflections. The large number of first- and second-order satellite reflections with relatively strong intensities indicates a significant modulation. No average structure solution could be obtained on the basis of the main reflections only and hence the structure solution was performed in two suitable superstructure approximations, including satellite intensities. Positional modulation functions and modulation functions for the anisotropic atomic displacement parameters were introduced. The modulation originates from a competition between intramolecular and intermolecular forces, which is reflected, in the superspace formalism, in the modification of hydrogen bonds along the internal space variable
t.
Supporting information
Data collection: (X-AREA, Stoe & Cie, 2002); cell refinement: (NADA; Schönleber et al., 2001); data reduction: (X-AREA, Stoe & Cie, 2002); program(s) used to solve structure: (DIRDIF, Beurskens et al., 1996); program(s) used to refine structure: (Jana2000; Petricek and Dusek, 2000); software used to prepare material for publication: (Jana2000; Petricek and Dusek, 2000).
6'-methoxy (8,9
R)-cinchonan-9-ol
top
Crystal data top
C20H25N2O2+·C8H7O3− | F(000) = 508 |
Mr = 476.57 | Dx = 1.303 (1) Mg m−3 |
Monoclinic, P21(α0γ)0† | Mo Kα radiation, λ = 0.71069 Å |
q = 0.33290a* + -0.27130c* | Cell parameters from 7295 reflections |
a = 6.614 (3) Å | θ = 4.0–49.2° |
b = 18.552 (7) Å | µ = 0.09 mm−1 |
c = 10.377 (4) Å | T = 291 K |
β = 107.47 (3)° | Platelet, colourless |
V = 1214.6 (9) Å3 | 0.24 × 0.18 × 0.08 mm |
Z = 2 | |
† Symmetry operations: (1) x1, x2, x3, x4; (2) −x1, 1/2+x2, −x3, −x4.
|
Data collection top
STOE IPDS II diffractometer | 11584 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.085 |
Graphite monochromator | θmax = 24.6°, θmin = 1.2° |
Detector resolution: 6.7 pixels mm-1 | h = −8→8 |
ω scans | k = −21→21 |
204354 measured reflections | l = −13→13 |
26261 independent reflections | |
Refinement top
Refinement on F | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.074 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0004F2) |
wR(F2) = 0.079 | (Δ/σ)max = 0.0002 |
S = 1.25 | Δρmax = 0.88 e Å−3 |
26261 reflections | Δρmin = −0.81 e Å−3 |
1636 parameters | Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974) |
90 restraints | Extinction coefficient: 1.22 (14) |
Crystal data top
C20H25N2O2+·C8H7O3− | β = 107.47 (3)° |
Mr = 476.57 | V = 1214.6 (9) Å3 |
Monoclinic, P21(α0γ)0† | Z = 2 |
q = 0.33290a* + -0.27130c* | Mo Kα radiation |
a = 6.614 (3) Å | µ = 0.09 mm−1 |
b = 18.552 (7) Å | T = 291 K |
c = 10.377 (4) Å | 0.24 × 0.18 × 0.08 mm |
† Symmetry operations: (1) x1, x2, x3, x4; (2) −x1, 1/2+x2, −x3, −x4.
|
Data collection top
STOE IPDS II diffractometer | 11584 reflections with I > 2σ(I) |
204354 measured reflections | Rint = 0.085 |
26261 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.074 | 90 restraints |
wR(F2) = 0.079 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.25 | Δρmax = 0.88 e Å−3 |
26261 reflections | Δρmin = −0.81 e Å−3 |
1636 parameters | |
Special details top
Refinement. Refinement of F against ALL reflections. The threshold expression of I > σ(I) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N01 | 0.4126 (6) | −0.0320 (2) | 0.1798 (5) | 0.0493 (7) | |
C02 | 0.2309 (4) | −0.08253 (15) | 0.1563 (3) | 0.0628 (11) | |
C03 | 0.3044 (4) | −0.15919 (15) | 0.1622 (3) | 0.0726 (12) | |
C04 | 0.5467 (6) | −0.1582 (2) | 0.1942 (5) | 0.0680 (11) | |
C05 | 0.5999 (7) | −0.1181 (3) | 0.0809 (5) | 0.0833 (13) | |
C06 | 0.5117 (7) | −0.0430 (2) | 0.0689 (5) | 0.0668 (11) | |
C07 | 0.6459 (6) | −0.1206 (2) | 0.3262 (5) | 0.0568 (10) | |
C08 | 0.5616 (6) | −0.0441 (2) | 0.3196 (5) | 0.0458 (8) | |
C09 | 0.7301 (4) | 0.01459 (14) | 0.3590 (3) | 0.0500 (10) | |
C10 | 0.2435 (7) | −0.2059 (3) | 0.2576 (6) | 0.139 (3) | |
C11 | 0.1255 (8) | −0.2342 (3) | 0.2830 (6) | 0.156 (3) | |
O12 | 0.8856 (2) | 0 | 0.29369 (17) | 0.0618 (7) | |
N13 | 1.0236 (6) | 0.0067 (3) | 0.7947 (5) | 0.0705 (10) | |
C14 | 1.1108 (4) | −0.01893 (18) | 0.7074 (3) | 0.0769 (14) | |
C15 | 1.0202 (6) | −0.0165 (3) | 0.5680 (5) | 0.0597 (12) | |
C16 | 0.8281 (4) | 0.01473 (14) | 0.5110 (3) | 0.0481 (9) | |
C17 | 0.7290 (6) | 0.0455 (3) | 0.6014 (5) | 0.0488 (9) | |
C18 | 0.5379 (7) | 0.0835 (3) | 0.5587 (5) | 0.0516 (10) | |
C19 | 0.4551 (4) | 0.11277 (15) | 0.6540 (3) | 0.0565 (11) | |
C20 | 0.5536 (7) | 0.1009 (3) | 0.7921 (5) | 0.0687 (13) | |
C21 | 0.7351 (7) | 0.0656 (3) | 0.8351 (5) | 0.0639 (11) | |
C22 | 0.8308 (7) | 0.0383 (3) | 0.7412 (5) | 0.0567 (11) | |
O23 | 0.2768 (6) | 0.1533 (2) | 0.6244 (4) | 0.0772 (9) | |
C24 | 0.1831 (7) | 0.1752 (3) | 0.4887 (5) | 0.0904 (17) | |
C25 | 0.0949 (4) | 0.12926 (16) | 0.1550 (3) | 0.0680 (13) | |
O26 | 0.1965 (7) | 0.0773 (2) | 0.2193 (5) | 0.0719 (10) | |
O27 | −0.0801 (6) | 0.1467 (2) | 0.1565 (5) | 0.0943 (11) | |
C28 | 0.2029 (4) | 0.17360 (16) | 0.0763 (3) | 0.0604 (13) | |
O29 | 0.3475 (6) | 0.1280 (2) | 0.0417 (5) | 0.0681 (11) | |
C30 | 0.3160 (7) | 0.2344 (2) | 0.1608 (5) | 0.0573 (12) | |
C31 | 0.2051 (5) | 0.29090 (17) | 0.1873 (3) | 0.0766 (14) | |
C32 | 0.3056 (8) | 0.3450 (3) | 0.2691 (5) | 0.0912 (17) | |
C33 | 0.5170 (9) | 0.3460 (3) | 0.3240 (6) | 0.0976 (19) | |
C34 | 0.6244 (8) | 0.2900 (3) | 0.2944 (6) | 0.0840 (17) | |
C35 | 0.5274 (8) | 0.2354 (3) | 0.2130 (5) | 0.0596 (13) | |
H01 | 0.359 (3) | 0.0124 (8) | 0.1780 (18) | 0.057959 (3)* | |
H02a | 0.128 (3) | −0.0700 (10) | 0.0622 (17) | 0.072158 (4)* | |
H02b | 0.167 (3) | −0.0712 (11) | 0.2303 (19) | 0.072158 (4)* | |
H03 | 0.204 (3) | −0.1467 (10) | 0.1032 (18) | 0.080441 (5)* | |
H04 | 0.600 (3) | −0.2093 (9) | 0.197 (2) | 0.077412 (5)* | |
H05a | 0.749 (3) | −0.1173 (11) | 0.093 (2) | 0.099116 (5)* | |
H05b | 0.530 (3) | −0.1423 (11) | −0.008 (2) | 0.099116 (5)* | |
H06a | 0.397 (3) | −0.0320 (10) | −0.0141 (19) | 0.080392 (4)* | |
H06b | 0.612 (3) | −0.0041 (9) | 0.079 (2) | 0.080392 (4)* | |
H07a | 0.803 (2) | −0.1199 (9) | 0.3480 (19) | 0.066256 (4)* | |
H07b | 0.608 (3) | −0.1468 (9) | 0.3968 (18) | 0.066256 (4)* | |
H08 | 0.476 (3) | −0.0412 (9) | 0.3811 (18) | 0.054495 (3)* | |
H09 | 0.660 (3) | 0.0626 (9) | 0.3255 (19) | 0.062600 (4)* | |
H10 | 0.345 (3) | −0.1956 (14) | 0.3375 (19) | 0.159216 (8)* | |
H11a | 0.017 (3) | −0.2384 (15) | 0.212 (2) | 0.191557 (11* | |
H11b | 0.121 (3) | −0.2617 (14) | 0.358 (2) | 0.191557 (11* | |
H12 | 0.899 (4) | 0.0405 (10) | 0.256 (3) | 0.097256 (3)* | |
H14 | 1.244 (3) | −0.0436 (12) | 0.739 (2) | 0.087939 (5)* | |
H15 | 1.084 (3) | −0.0399 (11) | 0.5055 (19) | 0.071412 (4)* | |
H18 | 0.475 (3) | 0.0884 (11) | 0.4688 (17) | 0.062407 (4)* | |
H20 | 0.485 (3) | 0.1186 (12) | 0.855 (2) | 0.084441 (6)* | |
H21 | 0.808 (3) | 0.0628 (11) | 0.9269 (18) | 0.076355 (5)* | |
H24a | 0.069 (3) | 0.2085 (12) | 0.489 (3) | 0.133279 (9)* | |
H24b | 0.289 (4) | 0.2010 (13) | 0.457 (3) | 0.133279 (9)* | |
H24c | 0.136 (4) | 0.1327 (11) | 0.431 (2) | 0.133279 (9)* | |
H28 | 0.131 (4) | 0.1942 (11) | −0.0198 (18) | 0.074727 (6)* | |
H29 | 0.345 (5) | 0.1574 (13) | −0.027 (3) | 0.105174 (6)* | |
H31 | 0.052 (2) | 0.2883 (13) | 0.153 (3) | 0.094367 (6)* | |
H32 | 0.224 (3) | 0.3778 (12) | 0.301 (3) | 0.114915 (8)* | |
H33 | 0.586 (3) | 0.3836 (12) | 0.381 (3) | 0.120118 (9)* | |
H34 | 0.776 (3) | 0.2864 (12) | 0.327 (3) | 0.097252 (6)* | |
H35 | 0.608 (3) | 0.1908 (10) | 0.198 (2) | 0.068678 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N01 | 0.0512 (10) | 0.0507 (10) | 0.0444 (13) | 0.0058 (9) | 0.0122 (9) | −0.0014 (8) |
C02 | 0.0503 (13) | 0.0688 (16) | 0.063 (2) | −0.0064 (12) | 0.0074 (13) | −0.0062 (13) |
C03 | 0.0644 (16) | 0.0527 (14) | 0.086 (2) | 0.0030 (13) | 0.0002 (15) | −0.0064 (14) |
C04 | 0.0673 (16) | 0.0551 (13) | 0.073 (2) | 0.0103 (12) | 0.0083 (15) | −0.0209 (14) |
C05 | 0.0823 (18) | 0.108 (2) | 0.060 (2) | 0.0193 (17) | 0.0219 (16) | −0.0193 (17) |
C06 | 0.0742 (15) | 0.0836 (17) | 0.0452 (17) | 0.0009 (14) | 0.0218 (13) | −0.0026 (13) |
C07 | 0.0556 (13) | 0.0481 (13) | 0.0636 (19) | 0.0017 (11) | 0.0131 (12) | 0.0011 (12) |
C08 | 0.0455 (11) | 0.0511 (12) | 0.0410 (15) | 0.0001 (10) | 0.0133 (11) | −0.0046 (10) |
C09 | 0.0517 (13) | 0.0541 (14) | 0.0523 (18) | −0.0074 (11) | 0.0280 (13) | −0.0098 (12) |
C10 | 0.078 (2) | 0.107 (3) | 0.217 (6) | −0.016 (2) | 0.022 (3) | 0.032 (3) |
C11 | 0.120 (4) | 0.185 (5) | 0.179 (6) | 0.047 (3) | 0.067 (4) | 0.053 (4) |
O12 | 0.0627 (9) | 0.0753 (12) | 0.0584 (13) | −0.0095 (9) | 0.0348 (9) | −0.0080 (10) |
N13 | 0.0645 (13) | 0.0874 (16) | 0.0533 (16) | −0.0062 (12) | 0.0081 (12) | −0.0077 (13) |
C14 | 0.0607 (15) | 0.102 (3) | 0.060 (2) | 0.0009 (16) | 0.0051 (16) | −0.0117 (19) |
C15 | 0.0570 (14) | 0.069 (2) | 0.054 (2) | −0.0042 (14) | 0.0187 (14) | −0.0107 (15) |
C16 | 0.0426 (12) | 0.0545 (14) | 0.0480 (17) | −0.0142 (11) | 0.0150 (12) | −0.0103 (12) |
C17 | 0.0528 (13) | 0.0523 (13) | 0.0432 (17) | −0.0144 (11) | 0.0175 (12) | −0.0085 (11) |
C18 | 0.0560 (15) | 0.0583 (12) | 0.0433 (16) | −0.0070 (11) | 0.0191 (13) | −0.0060 (12) |
C19 | 0.0600 (16) | 0.0595 (14) | 0.054 (2) | −0.0029 (13) | 0.0238 (15) | −0.0091 (12) |
C20 | 0.088 (2) | 0.0763 (18) | 0.049 (2) | −0.0124 (16) | 0.0316 (18) | −0.0120 (14) |
C21 | 0.0788 (18) | 0.0721 (16) | 0.0419 (18) | −0.0159 (15) | 0.0197 (15) | −0.0057 (14) |
C22 | 0.0603 (15) | 0.0598 (14) | 0.0510 (19) | −0.0119 (12) | 0.0182 (14) | −0.0077 (12) |
O23 | 0.0872 (14) | 0.0835 (12) | 0.0694 (16) | 0.0174 (11) | 0.0361 (12) | −0.0111 (11) |
C24 | 0.100 (3) | 0.099 (2) | 0.070 (3) | 0.034 (2) | 0.023 (2) | −0.0018 (19) |
C25 | 0.074 (2) | 0.0651 (17) | 0.067 (2) | 0.0057 (16) | 0.0231 (17) | −0.0227 (15) |
O26 | 0.0836 (15) | 0.0530 (10) | 0.0924 (18) | 0.0016 (10) | 0.0463 (14) | 0.0027 (10) |
O27 | 0.0641 (13) | 0.1154 (16) | 0.104 (2) | 0.0055 (12) | 0.0265 (13) | −0.0199 (14) |
C28 | 0.062 (2) | 0.0663 (18) | 0.060 (2) | 0.0125 (16) | 0.030 (2) | −0.0001 (16) |
O29 | 0.0774 (17) | 0.0705 (14) | 0.065 (2) | 0.0175 (13) | 0.0335 (16) | 0.0140 (13) |
C30 | 0.0656 (18) | 0.0558 (15) | 0.056 (2) | 0.0011 (14) | 0.0274 (16) | 0.0109 (14) |
C31 | 0.088 (2) | 0.0693 (18) | 0.081 (2) | 0.0161 (17) | 0.0381 (19) | 0.0096 (16) |
C32 | 0.121 (3) | 0.0664 (19) | 0.103 (3) | −0.003 (2) | 0.059 (3) | −0.0052 (19) |
C33 | 0.128 (3) | 0.080 (3) | 0.096 (3) | −0.038 (2) | 0.049 (3) | −0.016 (2) |
C34 | 0.081 (2) | 0.078 (2) | 0.087 (3) | −0.0054 (19) | 0.015 (2) | −0.021 (2) |
C35 | 0.0666 (19) | 0.0554 (17) | 0.051 (2) | −0.0083 (15) | 0.0095 (17) | −0.0057 (16) |
Geometric parameters (Å, º) top | Average | Minimum | Maximum |
C02—N01 | 1.501 (15) | 1.486 (15) | 1.526 (15) |
C03—C02 | 1.52 (7) | 1.43 (6) | 1.61 (6) |
C03—C04 | 1.55 (9) | 1.52 (8) | 1.60 (9) |
C03—C10 | 1.49 (9) | 1.46 (8) | 1.54 (8) |
C04—C05 | 1.523 (19) | 1.519 (19) | 1.533 (18) |
C04—C07 | 1.509 (17) | 1.502 (18) | 1.517 (18) |
C05—C06 | 1.518 (16) | 1.503 (16) | 1.541 (17) |
C06—N01 | 1.50 (2) | 1.50 (2) | 1.52 (2) |
C07—C08 | 1.534 (19) | 1.518 (19) | 1.558 (19) |
C08—N01 | 1.511 (16) | 1.505 (16) | 1.520 (16) |
C09—C08 | 1.535 (18) | 1.504 (18) | 1.580 (18) |
C09—C16 | 1.517 (17) | 1.515 (17) | 1.521 (17) |
C10—C11 | 1.17 (6) | 1.04 (6) | 1.40 (6) |
O12—C09 | 1.42 (2) | 1.42 (2) | 1.44 (2) |
C14—N13 | 1.313 (18) | 1.301 (18) | 1.328 (18) |
C14—C15 | 1.391 (17) | 1.391 (17) | 1.393 (17) |
C16—C15 | 1.38 (2) | 1.31 (2) | 1.44 (2) |
C16—C17 | 1.42 (2) | 1.39 (2) | 1.46 (2) |
C17—C18 | 1.417 (15) | 1.399 (15) | 1.440 (15) |
C17—C22 | 1.411 (13) | 1.410 (13) | 1.413 (12) |
C18—C19 | 1.38 (5) | 1.33 (5) | 1.43 (5) |
C19—O23 | 1.37 (5) | 1.35 (5) | 1.38 (4) |
C20—C19 | 1.40 (4) | 1.37 (4) | 1.44 (4) |
C20—C21 | 1.339 (15) | 1.322 (15) | 1.361 (15) |
C21—C22 | 1.418 (16) | 1.405 (16) | 1.434 (15) |
C22—N13 | 1.378 (12) | 1.361 (12) | 1.399 (13) |
C24—O23 | 1.42 (2) | 1.42 (2) | 1.42 (2) |
C25—O26 | 1.27 (3) | 1.25 (3) | 1.37 (2) |
C25—O27 | 1.23 (2) | 1.21 (2) | 1.32 (3) |
C25—C28 | 1.51 (2) | 1.44 (2) | 1.62 (2) |
C28—O29 | 1.46 (3) | 1.40 (3) | 1.60 (2) |
C28—C30 | 1.51 (2) | 1.48 (2) | 1.55 (2) |
C30—C31 | 1.39 (3) | 1.30 (3) | 1.50 (3) |
C30—C35 | 1.38 (4) | 1.28 (4) | 1.45 (4) |
C31—C32 | 1.38 (2) | 1.35 (2) | 1.42 (2) |
C32—C33 | 1.38 (2) | 1.34 (2) | 1.45 (2) |
C33—C34 | 1.38 (2) | 1.35 (2) | 1.46 (2) |
C34—C35 | 1.38 (2) | 1.35 (2) | 1.42 (2) |
N01—H01 | 0.91 (2) | 0.90 (2) | 0.92 (2) |
C02—H02a | 1.04 (3) | 1.04 (3) | 1.05 (3) |
C02—H02b | 1.01 (3) | 1.00 (3) | 1.02 (3) |
C03—H03 | 1.23 (11) | 0.79 (12) | 1.82 (12) |
C04—H04 | 1.02 (2) | 1.01 (2) | 1.04 (2) |
C05—H05a | 0.96 (3) | 0.95 (3) | 0.98 (3) |
C05—H05b | 1.01 (3) | 1.01 (3) | 1.02 (3) |
C06—H06a | 0.99 (2) | 0.98 (2) | 0.99 (2) |
C06—H06b | 0.97 (3) | 0.96 (3) | 0.99 (2) |
C07—H07a | 1.01 (3) | 1.00 (3) | 1.02 (3) |
C07—H07b | 0.98 (3) | 0.97 (3) | 0.98 (3) |
C08—H08 | 0.98 (3) | 0.97 (3) | 0.99 (3) |
C09—H09 | 1.02 (3) | 1.02 (3) | 1.04 (3) |
C10—H10 | 1.46 (9) | 0.92 (8) | 2.16 (10) |
C11—H11a | 1.38 (10) | 0.87 (9) | 2.04 (10) |
C11—H11b | 1.04 (10) | 0.94 (10) | 1.23 (9) |
O12—H12 | 0.87 (3) | 0.86 (3) | 0.88 (3) |
C14—H14 | 0.97 (2) | 0.96 (2) | 0.99 (3) |
C15—H15 | 0.98 (3) | 0.97 (3) | 1.00 (3) |
C18—H18 | 0.91 (2) | 0.90 (2) | 0.91 (2) |
C20—H20 | 0.97 (3) | 0.96 (3) | 0.98 (3) |
C21—H21 | 0.93 (2) | 0.93 (2) | 0.93 (2) |
C24—H24a | 0.99 (4) | 0.98 (4) | 1.00 (4) |
C24—H24b | 0.99 (4) | 0.98 (4) | 1.01 (4) |
C24—H24c | 0.99 (4) | 0.99 (4) | 1.01 (4) |
C28—H28 | 1.08 (4) | 1.04 (4) | 1.21 (4) |
O29—H29 | 0.93 (4) | 0.90 (4) | 1.01 (5) |
C31—H31 | 0.99 (3) | 0.97 (3) | 1.04 (3) |
C32—H32 | 0.96 (4) | 0.94 (4) | 1.02 (3) |
C33—H33 | 0.96 (3) | 0.94 (3) | 0.98 (4) |
C34—H34 | 0.99 (3) | 0.96 (3) | 1.04 (3) |
C35—H35 | 1.04 (4) | 1.02 (4) | 1.10 (3) |
| | | |
C02—N01—C06 | 107.9 (10) | 107.6 (10) | 108.2 (10) |
C02—N01—C08 | 109.3 (11) | 109.0 (11) | 109.6 (11) |
C02—N01—H01 | 106.2 (18) | 106.2 (17) | 106.3 (18) |
C06—N01—C08 | 113.7 (10) | 112.9 (10) | 114.2 (10) |
C06—N01—H01 | 112 (2) | 112 (2) | 113 (2) |
C08—N01—H01 | 107.5 (18) | 107.3 (18) | 107.7 (17) |
C03—C02—N01 | 111 (3) | 109 (3) | 113 (3) |
C03—C02—H02a | 111 (3) | 107 (3) | 117 (3) |
C03—C02—H02b | 112 (4) | 106 (4) | 119 (4) |
N01—C02—H02a | 106.7 (19) | 106.4 (19) | 107.0 (18) |
N01—C02—H02b | 104.4 (17) | 104.1 (17) | 104.7 (18) |
H02a—C02—H02b | 111 (2) | 110 (2) | 111 (2) |
C02—C03—C04 | 107 (4) | 103 (4) | 111 (4) |
C10—C03—C02 | 116 (6) | 109 (6) | 124 (6) |
C10—C03—C04 | 111 (4) | 104 (4) | 118 (5) |
C02—C03—H03 | 66 (6) | 3(4) | 115 (5) |
C04—C03—H03 | 115 (9) | 94 (7) | 141 (11) |
C10—C03—H03 | 111 (8) | 105 (7) | 116 (6) |
C03—C04—C05 | 108 (3) | 103 (3) | 112 (3) |
C03—C04—C07 | 110 (3) | 104 (3) | 116 (3) |
C03—C04—H04 | 109 (3) | 106 (3) | 112 (3) |
C05—C04—H04 | 109 (2) | 109 (2) | 109 (2) |
C05—C04—C07 | 109.4 (9) | 108.5 (9) | 109.9 (9) |
C07—C04—H04 | 111.2 (17) | 110.9 (17) | 111.9 (17) |
C04—C05—C06 | 110.2 (11) | 109.9 (11) | 110.5 (11) |
C04—C05—H05a | 112.2 (19) | 111.8 (19) | 112.9 (18) |
C04—C05—H05b | 109.6 (19) | 108.7 (18) | 110.1 (19) |
C06—C05—H05a | 110.8 (19) | 110.7 (19) | 110.9 (19) |
C06—C05—H05b | 106.4 (17) | 106.1 (17) | 107.1 (17) |
H05a—C05—H05b | 108 (3) | 107 (3) | 108 (3) |
C05—C06—N01 | 108.3 (10) | 108.0 (10) | 108.9 (9) |
C05—C06—H06a | 116.3 (18) | 116.1 (18) | 116.4 (17) |
C05—C06—H06b | 116.6 (18) | 116.6 (18) | 116.7 (18) |
N01—C06—H06a | 104 (2) | 103 (2) | 104 (2) |
N01—C06—H06b | 104.9 (19) | 104.7 (19) | 105 (2) |
H06a—C06—H06b | 106 (2) | 105 (2) | 106 (2) |
C04—C07—C08 | 110.0 (9) | 109.7 (9) | 110.7 (9) |
C04—C07—H07a | 111 (2) | 110 (2) | 111 (2) |
C04—C07—H07b | 107.7 (18) | 106.8 (18) | 108.3 (18) |
H07a—C07—H07b | 109 (2) | 109 (2) | 110 (2) |
C08—C07—H07a | 110.0 (19) | 110.0 (18) | 110.1 (19) |
C08—C07—H07b | 109 (2) | 109 (2) | 109 (2) |
C09—C08—C07 | 115.2 (11) | 111.8 (11) | 117.9 (11) |
C07—C08—H08 | 107.7 (18) | 107.4 (18) | 108.1 (17) |
C09—C08—H08 | 108.1 (17) | 103.1 (17) | 113.1 (17) |
N01—C08—H08 | 105.8 (17) | 105.0 (16) | 106.4 (17) |
C07—C08—N01 | 108.0 (9) | 107.8 (10) | 108.2 (9) |
C09—C08—N01 | 111.6 (10) | 108.9 (10) | 114.6 (10) |
H09—C09—C08 | 108.1 (17) | 102.0 (17) | 111.6 (17) |
O12—C09—C08 | 108.4 (12) | 106.5 (11) | 111.3 (12) |
O12—C09—C16 | 110.4 (11) | 109.8 (11) | 110.7 (11) |
C16—C09—C08 | 109.2 (12) | 107.1 (12) | 112.5 (12) |
C16—C09—H09 | 111.4 (19) | 111.2 (19) | 111.9 (19) |
O12—C09—H09 | 109 (2) | 109 (2) | 109 (2) |
C03—C10—H10 | 105 (5) | 99 (5) | 111 (4) |
C03—C10—C11 | 134 (4) | 115 (4) | 149 (4) |
C11—C10—H10 | 117 (5) | 105 (7) | 127 (4) |
C10—C11—H11a | 120 (6) | 108 (8) | 132 (4) |
C10—C11—H11b | 114 (7) | 91 (6) | 134 (8) |
H11a—C11—H11b | 125 (8) | 115 (9) | 136 (7) |
C09—O12—H12 | 104 (3) | 103 (3) | 104 (3) |
C14—N13—C22 | 116.2 (10) | 115.5 (10) | 117.1 (10) |
C15—C14—N13 | 124.3 (9) | 123.7 (9) | 124.7 (9) |
C15—C14—H14 | 116 (2) | 115 (2) | 116 (2) |
N13—C14—H14 | 120 (2) | 119 (2) | 121 (2) |
C16—C15—C14 | 121.0 (12) | 119.3 (12) | 123.0 (12) |
C16—C15—H15 | 116.6 (17) | 114.4 (17) | 119.0 (17) |
C14—C15—H15 | 122.2 (16) | 121.7 (16) | 122.7 (16) |
C09—C16—C15 | 120.2 (14) | 118.3 (15) | 121.9 (15) |
C09—C16—C17 | 123.0 (13) | 116.8 (13) | 127.7 (14) |
C15—C16—C17 | 116.8 (11) | 111.5 (10) | 121.2 (11) |
C16—C17—C18 | 123.7 (10) | 120.2 (10) | 127.7 (10) |
C16—C17—C22 | 117.7 (9) | 113.9 (9) | 121.0 (10) |
C18—C17—C22 | 118.6 (10) | 118.3 (10) | 118.8 (10) |
C17—C18—H18 | 118 (2) | 118 (2) | 118 (2) |
C17—C18—C19 | 119.6 (17) | 118.3 (18) | 121.5 (17) |
H18—C18—C19 | 122 (2) | 121 (2) | 124 (3) |
C18—C19—C20 | 120 (3) | 117 (3) | 125 (3) |
C18—C19—O23 | 125 (3) | 122 (3) | 128 (3) |
C20—C19—O23 | 115 (3) | 113 (3) | 117 (3) |
C21—C20—C19 | 121 (2) | 118 (2) | 123 (2) |
H20—C20—C19 | 118 (2) | 116 (2) | 120 (2) |
C21—C20—H20 | 121.3 (18) | 120.7 (18) | 122.2 (18) |
C20—C21—C22 | 120.5 (10) | 119.8 (10) | 121.3 (10) |
C20—C21—H21 | 120 (2) | 120 (2) | 121 (2) |
C22—C21—H21 | 118.8 (19) | 118.1 (19) | 119.3 (19) |
C17—C22—C21 | 119.7 (8) | 119.1 (8) | 120.3 (8) |
C17—C22—N13 | 123.9 (10) | 123.5 (10) | 124.1 (10) |
C21—C22—N13 | 116.4 (9) | 115.7 (9) | 117.3 (9) |
C19—O23—C24 | 118 (2) | 117 (2) | 119 (3) |
O23—C24—H24a | 106 (3) | 105 (3) | 107 (3) |
O23—C24—H24b | 109 (2) | 109 (2) | 110 (2) |
O23—C24—H24c | 110 (3) | 109 (3) | 110 (3) |
H24a—C24—H24b | 109 (4) | 109 (4) | 109 (4) |
H24a—C24—H24c | 114 (3) | 114 (3) | 115 (3) |
H24b—C24—H24c | 108 (4) | 108 (4) | 109 (4) |
O26—C25—O27 | 124 (2) | 123.4 (19) | 125 (2) |
O26—C25—C28 | 117.1 (17) | 112.8 (18) | 124.0 (15) |
O27—C25—C28 | 118.5 (16) | 112.5 (15) | 122.9 (16) |
C25—C28—C30 | 109.3 (16) | 106.6 (16) | 112.0 (16) |
C25—C28—O29 | 107.0 (12) | 97.3 (12) | 113.3 (12) |
C25—C28—H28 | 124 (2) | 118 (2) | 130.2 (19) |
C30—C28—O29 | 109.9 (17) | 107.0 (15) | 111.3 (15) |
C30—C28—H28 | 108 (2) | 102 (2) | 112 (2) |
O29—C28—H28 | 97 (3) | 96 (2) | 100 (3) |
C28—O29—H29 | 90 (3) | 88 (3) | 92 (3) |
C28—C30—C31 | 120 (2) | 113.2 (19) | 124 (3) |
C28—C30—C35 | 122 (2) | 118.3 (18) | 127 (2) |
C31—C30—C35 | 118.3 (17) | 113.5 (15) | 123.5 (19) |
C30—C31—C32 | 120.4 (17) | 116.7 (18) | 122.7 (16) |
C30—C31—H31 | 117 (3) | 115 (3) | 121 (3) |
C32—C31—H31 | 122 (3) | 120 (3) | 122 (3) |
C31—C32—C33 | 121.8 (15) | 120.7 (13) | 122.2 (15) |
C31—C32—H32 | 118 (2) | 118 (2) | 119 (2) |
C33—C32—H32 | 119 (2) | 118 (2) | 120 (2) |
C32—C33—C34 | 116.9 (13) | 116.3 (13) | 119.1 (13) |
C32—C33—H33 | 121 (3) | 120 (2) | 122 (3) |
C34—C33—H33 | 122 (3) | 121 (2) | 122 (2) |
C33—C34—C35 | 122.3 (14) | 121.3 (13) | 122.6 (14) |
C33—C34—H34 | 123 (2) | 123 (2) | 125 (2) |
C35—C34—H34 | 114 (3) | 113 (2) | 115 (3) |
C30—C35—C34 | 120.1 (17) | 117.5 (16) | 123.3 (18) |
C30—C35—H35 | 118 (2) | 114 (2) | 120 (2) |
C34—C35—H35 | 122 (2) | 121 (2) | 122 (2) |
Experimental details
Crystal data |
Chemical formula | C20H25N2O2+·C8H7O3− |
Mr | 476.57 |
Crystal system, space group | Monoclinic, P21(α0γ)0† |
Temperature (K) | 291 |
Wave vectors | q = 0.33290a* + -0.27130c* |
a, b, c (Å) | 6.614 (3), 18.552 (7), 10.377 (4) |
β (°) | 107.47 (3) |
V (Å3) | 1214.6 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.24 × 0.18 × 0.08 |
|
Data collection |
Diffractometer | STOE IPDS II diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 204354, 26261, 11584 |
Rint | 0.085 |
(sin θ/λ)max (Å−1) | 0.586 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.079, 1.25 |
No. of reflections | 26261 |
No. of parameters | 1636 |
No. of restraints | 90 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.88, −0.81 |
Selected geometric parameters (Å, º) top | Average | Minimum | Maximum |
C02—N01 | 1.501 (15) | 1.486 (15) | 1.526 (15) |
C03—C02 | 1.52 (7) | 1.43 (6) | 1.61 (6) |
C03—C04 | 1.55 (9) | 1.52 (8) | 1.60 (9) |
C03—C10 | 1.49 (9) | 1.46 (8) | 1.54 (8) |
C04—C05 | 1.523 (19) | 1.519 (19) | 1.533 (18) |
C04—C07 | 1.509 (17) | 1.502 (18) | 1.517 (18) |
C05—C06 | 1.518 (16) | 1.503 (16) | 1.541 (17) |
C06—N01 | 1.50 (2) | 1.50 (2) | 1.52 (2) |
C07—C08 | 1.534 (19) | 1.518 (19) | 1.558 (19) |
C08—N01 | 1.511 (16) | 1.505 (16) | 1.520 (16) |
C09—C08 | 1.535 (18) | 1.504 (18) | 1.580 (18) |
C09—C16 | 1.517 (17) | 1.515 (17) | 1.521 (17) |
C10—C11 | 1.17 (6) | 1.04 (6) | 1.40 (6) |
O12—C09 | 1.42 (2) | 1.42 (2) | 1.44 (2) |
C14—N13 | 1.313 (18) | 1.301 (18) | 1.328 (18) |
C14—C15 | 1.391 (17) | 1.391 (17) | 1.393 (17) |
C16—C15 | 1.38 (2) | 1.31 (2) | 1.44 (2) |
C16—C17 | 1.42 (2) | 1.39 (2) | 1.46 (2) |
C17—C18 | 1.417 (15) | 1.399 (15) | 1.440 (15) |
C17—C22 | 1.411 (13) | 1.410 (13) | 1.413 (12) |
C18—C19 | 1.38 (5) | 1.33 (5) | 1.43 (5) |
C19—O23 | 1.37 (5) | 1.35 (5) | 1.38 (4) |
C20—C19 | 1.40 (4) | 1.37 (4) | 1.44 (4) |
C20—C21 | 1.339 (15) | 1.322 (15) | 1.361 (15) |
C21—C22 | 1.418 (16) | 1.405 (16) | 1.434 (15) |
C22—N13 | 1.378 (12) | 1.361 (12) | 1.399 (13) |
C24—O23 | 1.42 (2) | 1.42 (2) | 1.42 (2) |
C25—O26 | 1.27 (3) | 1.25 (3) | 1.37 (2) |
C25—O27 | 1.23 (2) | 1.21 (2) | 1.32 (3) |
C25—C28 | 1.51 (2) | 1.44 (2) | 1.62 (2) |
C28—O29 | 1.46 (3) | 1.40 (3) | 1.60 (2) |
C28—C30 | 1.51 (2) | 1.48 (2) | 1.55 (2) |
C30—C31 | 1.39 (3) | 1.30 (3) | 1.50 (3) |
C30—C35 | 1.38 (4) | 1.28 (4) | 1.45 (4) |
C31—C32 | 1.38 (2) | 1.35 (2) | 1.42 (2) |
C32—C33 | 1.38 (2) | 1.34 (2) | 1.45 (2) |
C33—C34 | 1.38 (2) | 1.35 (2) | 1.46 (2) |
C34—C35 | 1.38 (2) | 1.35 (2) | 1.42 (2) |
N01—H01 | 0.91 (2) | 0.90 (2) | 0.92 (2) |
C02—H02a | 1.04 (3) | 1.04 (3) | 1.05 (3) |
C02—H02b | 1.01 (3) | 1.00 (3) | 1.02 (3) |
C03—H03 | 1.23 (11) | 0.79 (12) | 1.82 (12) |
C04—H04 | 1.02 (2) | 1.01 (2) | 1.04 (2) |
C05—H05a | 0.96 (3) | 0.95 (3) | 0.98 (3) |
C05—H05b | 1.01 (3) | 1.01 (3) | 1.02 (3) |
C06—H06a | 0.99 (2) | 0.98 (2) | 0.99 (2) |
C06—H06b | 0.97 (3) | 0.96 (3) | 0.99 (2) |
C07—H07a | 1.01 (3) | 1.00 (3) | 1.02 (3) |
C07—H07b | 0.98 (3) | 0.97 (3) | 0.98 (3) |
C08—H08 | 0.98 (3) | 0.97 (3) | 0.99 (3) |
C09—H09 | 1.02 (3) | 1.02 (3) | 1.04 (3) |
C10—H10 | 1.46 (9) | 0.92 (8) | 2.16 (10) |
C11—H11a | 1.38 (10) | 0.87 (9) | 2.04 (10) |
C11—H11b | 1.04 (10) | 0.94 (10) | 1.23 (9) |
O12—H12 | 0.87 (3) | 0.86 (3) | 0.88 (3) |
C14—H14 | 0.97 (2) | 0.96 (2) | 0.99 (3) |
C15—H15 | 0.98 (3) | 0.97 (3) | 1.00 (3) |
C18—H18 | 0.91 (2) | 0.90 (2) | 0.91 (2) |
C20—H20 | 0.97 (3) | 0.96 (3) | 0.98 (3) |
C21—H21 | 0.93 (2) | 0.93 (2) | 0.93 (2) |
C24—H24a | 0.99 (4) | 0.98 (4) | 1.00 (4) |
C24—H24b | 0.99 (4) | 0.98 (4) | 1.01 (4) |
C24—H24c | 0.99 (4) | 0.99 (4) | 1.01 (4) |
C28—H28 | 1.08 (4) | 1.04 (4) | 1.21 (4) |
O29—H29 | 0.93 (4) | 0.90 (4) | 1.01 (5) |
C31—H31 | 0.99 (3) | 0.97 (3) | 1.04 (3) |
C32—H32 | 0.96 (4) | 0.94 (4) | 1.02 (3) |
C33—H33 | 0.96 (3) | 0.94 (3) | 0.98 (4) |
C34—H34 | 0.99 (3) | 0.96 (3) | 1.04 (3) |
C35—H35 | 1.04 (4) | 1.02 (4) | 1.10 (3) |
| | | |
C02—N01—C06 | 107.9 (10) | 107.6 (10) | 108.2 (10) |
C02—N01—C08 | 109.3 (11) | 109.0 (11) | 109.6 (11) |
C02—N01—H01 | 106.2 (18) | 106.2 (17) | 106.3 (18) |
C06—N01—C08 | 113.7 (10) | 112.9 (10) | 114.2 (10) |
C06—N01—H01 | 112 (2) | 112 (2) | 113 (2) |
C08—N01—H01 | 107.5 (18) | 107.3 (18) | 107.7 (17) |
C03—C02—N01 | 111 (3) | 109 (3) | 113 (3) |
C03—C02—H02a | 111 (3) | 107 (3) | 117 (3) |
C03—C02—H02b | 112 (4) | 106 (4) | 119 (4) |
N01—C02—H02a | 106.7 (19) | 106.4 (19) | 107.0 (18) |
N01—C02—H02b | 104.4 (17) | 104.1 (17) | 104.7 (18) |
H02a—C02—H02b | 111 (2) | 110 (2) | 111 (2) |
C02—C03—C04 | 107 (4) | 103 (4) | 111 (4) |
C10—C03—C02 | 116 (6) | 109 (6) | 124 (6) |
C10—C03—C04 | 111 (4) | 104 (4) | 118 (5) |
C02—C03—H03 | 66 (6) | 3(4) | 115 (5) |
C04—C03—H03 | 115 (9) | 94 (7) | 141 (11) |
C10—C03—H03 | 111 (8) | 105 (7) | 116 (6) |
C03—C04—C05 | 108 (3) | 103 (3) | 112 (3) |
C03—C04—C07 | 110 (3) | 104 (3) | 116 (3) |
C03—C04—H04 | 109 (3) | 106 (3) | 112 (3) |
C05—C04—H04 | 109 (2) | 109 (2) | 109 (2) |
C05—C04—C07 | 109.4 (9) | 108.5 (9) | 109.9 (9) |
C07—C04—H04 | 111.2 (17) | 110.9 (17) | 111.9 (17) |
C04—C05—C06 | 110.2 (11) | 109.9 (11) | 110.5 (11) |
C04—C05—H05a | 112.2 (19) | 111.8 (19) | 112.9 (18) |
C04—C05—H05b | 109.6 (19) | 108.7 (18) | 110.1 (19) |
C06—C05—H05a | 110.8 (19) | 110.7 (19) | 110.9 (19) |
C06—C05—H05b | 106.4 (17) | 106.1 (17) | 107.1 (17) |
H05a—C05—H05b | 108 (3) | 107 (3) | 108 (3) |
C05—C06—N01 | 108.3 (10) | 108.0 (10) | 108.9 (9) |
C05—C06—H06a | 116.3 (18) | 116.1 (18) | 116.4 (17) |
C05—C06—H06b | 116.6 (18) | 116.6 (18) | 116.7 (18) |
N01—C06—H06a | 104 (2) | 103 (2) | 104 (2) |
N01—C06—H06b | 104.9 (19) | 104.7 (19) | 105 (2) |
H06a—C06—H06b | 106 (2) | 105 (2) | 106 (2) |
C04—C07—C08 | 110.0 (9) | 109.7 (9) | 110.7 (9) |
C04—C07—H07a | 111 (2) | 110 (2) | 111 (2) |
C04—C07—H07b | 107.7 (18) | 106.8 (18) | 108.3 (18) |
H07a—C07—H07b | 109 (2) | 109 (2) | 110 (2) |
C08—C07—H07a | 110.0 (19) | 110.0 (18) | 110.1 (19) |
C08—C07—H07b | 109 (2) | 109 (2) | 109 (2) |
C09—C08—C07 | 115.2 (11) | 111.8 (11) | 117.9 (11) |
C07—C08—H08 | 107.7 (18) | 107.4 (18) | 108.1 (17) |
C09—C08—H08 | 108.1 (17) | 103.1 (17) | 113.1 (17) |
N01—C08—H08 | 105.8 (17) | 105.0 (16) | 106.4 (17) |
C07—C08—N01 | 108.0 (9) | 107.8 (10) | 108.2 (9) |
C09—C08—N01 | 111.6 (10) | 108.9 (10) | 114.6 (10) |
H09—C09—C08 | 108.1 (17) | 102.0 (17) | 111.6 (17) |
O12—C09—C08 | 108.4 (12) | 106.5 (11) | 111.3 (12) |
O12—C09—C16 | 110.4 (11) | 109.8 (11) | 110.7 (11) |
C16—C09—C08 | 109.2 (12) | 107.1 (12) | 112.5 (12) |
C16—C09—H09 | 111.4 (19) | 111.2 (19) | 111.9 (19) |
O12—C09—H09 | 109 (2) | 109 (2) | 109 (2) |
C03—C10—H10 | 105 (5) | 99 (5) | 111 (4) |
C03—C10—C11 | 134 (4) | 115 (4) | 149 (4) |
C11—C10—H10 | 117 (5) | 105 (7) | 127 (4) |
C10—C11—H11a | 120 (6) | 108 (8) | 132 (4) |
C10—C11—H11b | 114 (7) | 91 (6) | 134 (8) |
H11a—C11—H11b | 125 (8) | 115 (9) | 136 (7) |
C09—O12—H12 | 104 (3) | 103 (3) | 104 (3) |
C14—N13—C22 | 116.2 (10) | 115.5 (10) | 117.1 (10) |
C15—C14—N13 | 124.3 (9) | 123.7 (9) | 124.7 (9) |
C15—C14—H14 | 116 (2) | 115 (2) | 116 (2) |
N13—C14—H14 | 120 (2) | 119 (2) | 121 (2) |
C16—C15—C14 | 121.0 (12) | 119.3 (12) | 123.0 (12) |
C16—C15—H15 | 116.6 (17) | 114.4 (17) | 119.0 (17) |
C14—C15—H15 | 122.2 (16) | 121.7 (16) | 122.7 (16) |
C09—C16—C15 | 120.2 (14) | 118.3 (15) | 121.9 (15) |
C09—C16—C17 | 123.0 (13) | 116.8 (13) | 127.7 (14) |
C15—C16—C17 | 116.8 (11) | 111.5 (10) | 121.2 (11) |
C16—C17—C18 | 123.7 (10) | 120.2 (10) | 127.7 (10) |
C16—C17—C22 | 117.7 (9) | 113.9 (9) | 121.0 (10) |
C18—C17—C22 | 118.6 (10) | 118.3 (10) | 118.8 (10) |
C17—C18—H18 | 118 (2) | 118 (2) | 118 (2) |
C17—C18—C19 | 119.6 (17) | 118.3 (18) | 121.5 (17) |
H18—C18—C19 | 122 (2) | 121 (2) | 124 (3) |
C18—C19—C20 | 120 (3) | 117 (3) | 125 (3) |
C18—C19—O23 | 125 (3) | 122 (3) | 128 (3) |
C20—C19—O23 | 115 (3) | 113 (3) | 117 (3) |
C21—C20—C19 | 121 (2) | 118 (2) | 123 (2) |
H20—C20—C19 | 118 (2) | 116 (2) | 120 (2) |
C21—C20—H20 | 121.3 (18) | 120.7 (18) | 122.2 (18) |
C20—C21—C22 | 120.5 (10) | 119.8 (10) | 121.3 (10) |
C20—C21—H21 | 120 (2) | 120 (2) | 121 (2) |
C22—C21—H21 | 118.8 (19) | 118.1 (19) | 119.3 (19) |
C17—C22—C21 | 119.7 (8) | 119.1 (8) | 120.3 (8) |
C17—C22—N13 | 123.9 (10) | 123.5 (10) | 124.1 (10) |
C21—C22—N13 | 116.4 (9) | 115.7 (9) | 117.3 (9) |
C19—O23—C24 | 118 (2) | 117 (2) | 119 (3) |
O23—C24—H24a | 106 (3) | 105 (3) | 107 (3) |
O23—C24—H24b | 109 (2) | 109 (2) | 110 (2) |
O23—C24—H24c | 110 (3) | 109 (3) | 110 (3) |
H24a—C24—H24b | 109 (4) | 109 (4) | 109 (4) |
H24a—C24—H24c | 114 (3) | 114 (3) | 115 (3) |
H24b—C24—H24c | 108 (4) | 108 (4) | 109 (4) |
O26—C25—O27 | 124 (2) | 123.4 (19) | 125 (2) |
O26—C25—C28 | 117.1 (17) | 112.8 (18) | 124.0 (15) |
O27—C25—C28 | 118.5 (16) | 112.5 (15) | 122.9 (16) |
C25—C28—C30 | 109.3 (16) | 106.6 (16) | 112.0 (16) |
C25—C28—O29 | 107.0 (12) | 97.3 (12) | 113.3 (12) |
C25—C28—H28 | 124 (2) | 118 (2) | 130.2 (19) |
C30—C28—O29 | 109.9 (17) | 107.0 (15) | 111.3 (15) |
C30—C28—H28 | 108 (2) | 102 (2) | 112 (2) |
O29—C28—H28 | 97 (3) | 96 (2) | 100 (3) |
C28—O29—H29 | 90 (3) | 88 (3) | 92 (3) |
C28—C30—C31 | 120 (2) | 113.2 (19) | 124 (3) |
C28—C30—C35 | 122 (2) | 118.3 (18) | 127 (2) |
C31—C30—C35 | 118.3 (17) | 113.5 (15) | 123.5 (19) |
C30—C31—C32 | 120.4 (17) | 116.7 (18) | 122.7 (16) |
C30—C31—H31 | 117 (3) | 115 (3) | 121 (3) |
C32—C31—H31 | 122 (3) | 120 (3) | 122 (3) |
C31—C32—C33 | 121.8 (15) | 120.7 (13) | 122.2 (15) |
C31—C32—H32 | 118 (2) | 118 (2) | 119 (2) |
C33—C32—H32 | 119 (2) | 118 (2) | 120 (2) |
C32—C33—C34 | 116.9 (13) | 116.3 (13) | 119.1 (13) |
C32—C33—H33 | 121 (3) | 120 (2) | 122 (3) |
C34—C33—H33 | 122 (3) | 121 (2) | 122 (2) |
C33—C34—C35 | 122.3 (14) | 121.3 (13) | 122.6 (14) |
C33—C34—H34 | 123 (2) | 123 (2) | 125 (2) |
C35—C34—H34 | 114 (3) | 113 (2) | 115 (3) |
C30—C35—C34 | 120.1 (17) | 117.5 (16) | 123.3 (18) |
C30—C35—H35 | 118 (2) | 114 (2) | 120 (2) |
C34—C35—H35 | 122 (2) | 121 (2) | 122 (2) |