The dipeptide L-Leu-L-Val can crystallize as a hydrate in the hexagonal space group P65 [Görbitz & Gundersen (1996). Acta Chem. Scand. 50, 537–543], but forms 1:1 solvates when methanol, ethanol and 2-propanol are used as precipitating agents. The structures of these complexes can be divided into hydrophobic and hydrophilic layers. The alcohol molecules are embedded in the hydrophobic layers, but with the hydroxyl groups as crucial parts of the hydrogen-bonding network. L-Leucyl-L-valine–methanol (1/1) crystallizes in the space group P21 with Z = 2. L-Leucyl-L-valine–ethanol (1/1) has very special systematic absences, and the structure could not be solved with direct methods. Unraveling the actual build-up of the crystal was an unusual process involving modeling with molecular graphics programs. The solution shows a structure which formally belongs to the space group P21, with four dipeptide molecules and four solvent molecules in the asymmetric unit (Z = 8). Additional non-crystallographic symmetry in three dimensions fixes all cell angles, including β, to 90°. L-Leucyl-L-valine–2-propanol (1/1) is structurally closely related to the ethanol solvate, but owing to a rare type of packing disorder the length of the a axis is halved (Z = 4, P212121). The hydrogen-bonding pattern is still the same as in the ethanol solvate, which means that the hydrogen-bond periodicity along the a axis in the 2-propanol solvate is two unit-cell lengths.
Supporting information
| Crystallographic Information File (CIF) Contains datablocks lvm, lve, lv2p, global |
| Structure factor file (CIF format) Contains datablock lvtest |
| Structure factor file (CIF format) Contains datablock lvm2 |
| Structure factor file (CIF format) Contains datablock lv2ptest |
CCDC references: 131750; 131751; 131752
For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXTL (Sheldrick, 1994); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXTL (Sheldrick, 1994).
(lvm)
L-leucyl-
L-valine methanol (1:1)
top
Crystal data top
C12H26N2O4 | F(000) = 288 |
Mr = 262.35 | Dx = 1.136 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.2890 (1) Å | Cell parameters from 8192 reflections |
b = 12.6877 (1) Å | µ = 0.08 mm−1 |
c = 11.4872 (1) Å | T = 150 K |
β = 95.8136 (5)° | Block, colourless |
V = 766.87 (1) Å3 | 0.50 × 0.40 × 0.35 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD diffractometer | 12154 independent reflections |
Radiation source: fine-focus sealed tube | 8119 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Sets of exposures each taken over 0.6° ω rotation scans | θmax = 49.8°, θmin = 1.8° |
Absorption correction: multiscan (SADABS; sheldrick, 1996) ? | h = −11→8 |
Tmin = 0.959, Tmax = 0.971 | k = −27→24 |
17325 measured reflections | l = −23→23 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.179 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Calculated w = 1/[σ2(Fo2) + (0.0864P)2] where P = (Fo2 + 2Fc2)/3 |
12153 reflections | (Δ/σ)max = 0.083 |
203 parameters | Δρmax = 0.64 e Å−3 |
1 restraint | Δρmin = −0.28 e Å−3 |
Crystal data top
C12H26N2O4 | V = 766.87 (1) Å3 |
Mr = 262.35 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.2890 (1) Å | µ = 0.08 mm−1 |
b = 12.6877 (1) Å | T = 150 K |
c = 11.4872 (1) Å | 0.50 × 0.40 × 0.35 mm |
β = 95.8136 (5)° | |
Data collection top
Siemens SMART CCD diffractometer | 12154 independent reflections |
Absorption correction: multiscan (SADABS; sheldrick, 1996) ? | 8119 reflections with I > 2σ(I) |
Tmin = 0.959, Tmax = 0.971 | Rint = 0.049 |
17325 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.066 | 1 restraint |
wR(F2) = 0.179 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.64 e Å−3 |
12153 reflections | Δρmin = −0.28 e Å−3 |
203 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement on F2 for ALL reflections except for 1 flagged by the user
for potential systematic errors. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 0.5902 (2) | 0.13448 (7) | 0.38070 (9) | 0.0296 (2) | |
O2A | 0.53664 (15) | −0.24568 (6) | 0.36754 (9) | 0.0269 (2) | |
O3A | 0.18301 (14) | −0.15513 (7) | 0.38891 (9) | 0.0280 (2) | |
N1A | 1.04959 (15) | 0.19362 (6) | 0.48622 (8) | 0.01919 (13) | |
H1A | 1.189 (4) | 0.210 (2) | 0.529 (2) | 0.046 (3)* | |
H2A | 0.924 (5) | 0.229 (2) | 0.522 (2) | 0.046 (3)* | |
H3A | 1.048 (5) | 0.213 (2) | 0.409 (2) | 0.046 (3)* | |
N2A | 0.72874 (13) | −0.03377 (6) | 0.35468 (7) | 0.01776 (12) | |
H4A | 0.844 (3) | −0.0758 (15) | 0.3650 (15) | 0.021* | |
C1A | 0.9823 (2) | 0.07992 (7) | 0.48747 (8) | 0.01674 (13) | |
H11A | 1.118 (3) | 0.0394 (8) | 0.4660 (4) | 0.020* | |
C2A | 0.9180 (2) | 0.04720 (9) | 0.60998 (9) | 0.0228 (2) | |
H21A | 0.8320 (13) | −0.0211 (10) | 0.60412 (12) | 0.027* | |
H22A | 0.7991 (17) | 0.0985 (7) | 0.6371 (4) | 0.027* | |
C3A | 1.1505 (3) | 0.03900 (11) | 0.70202 (11) | 0.0344 (3) | |
H31A | 1.268 (3) | 0.1002 (14) | 0.6916 (3) | 0.041* | |
C4A | 1.2954 (3) | −0.0642 (2) | 0.6887 (2) | 0.0461 (4) | |
H41A | 1.443 (3) | −0.0661 (7) | 0.7454 (15) | 0.074 (5)* | |
H42A | 1.348 (3) | −0.0683 (7) | 0.6108 (16) | 0.074 (5)* | |
H43A | 1.186 (2) | −0.1231 (11) | 0.7016 (17) | 0.074 (5)* | |
C5A | 1.0579 (6) | 0.0453 (2) | 0.82487 (15) | 0.0688 (8) | |
H51A | 1.211 (3) | 0.043 (2) | 0.8868 (12) | 0.098 (7)* | |
H52A | 0.942 (5) | −0.0172 (16) | 0.8367 (9) | 0.098 (7)* | |
H53A | 0.960 (5) | 0.1139 (17) | 0.8325 (8) | 0.098 (7)* | |
C6A | 0.7484 (2) | 0.06290 (7) | 0.39980 (8) | 0.01746 (13) | |
C7A | 0.50317 (15) | −0.07368 (7) | 0.28394 (8) | 0.01662 (12) | |
H71A | 0.385 (2) | −0.0219 (10) | 0.2752 (2) | 0.020* | |
C8A | 0.5706 (2) | −0.10789 (10) | 0.16254 (9) | 0.0244 (2) | |
H81A | 0.704 (3) | −0.1588 (10) | 0.1731 (2) | 0.029* | |
C9A | 0.6661 (3) | −0.01418 (14) | 0.09599 (12) | 0.0390 (3) | |
H91A | 0.809 (3) | 0.0182 (9) | 0.1423 (9) | 0.052 (4)* | |
H92A | 0.530 (2) | 0.0370 (9) | 0.0812 (12) | 0.052 (4)* | |
H93A | 0.720 (3) | −0.0382 (4) | 0.0222 (12) | 0.052 (4)* | |
C10A | 0.3425 (3) | −0.1595 (2) | 0.09337 (12) | 0.0416 (3) | |
H04A | 0.303 (2) | −0.2254 (14) | 0.1308 (11) | 0.066 (5)* | |
H05A | 0.3820 (15) | −0.1736 (14) | 0.0140 (15) | 0.066 (5)* | |
H06A | 0.197 (3) | −0.1126 (10) | 0.0912 (14) | 0.066 (5)* | |
C11A | 0.39812 (15) | −0.16608 (7) | 0.35230 (8) | 0.01668 (12) | |
O1B | 0.1617 (2) | 0.1901 (2) | 0.25127 (11) | 0.0375 (5) | 0.814 (6) |
H1B | 0.292 (6) | 0.177 (3) | 0.269 (3) | 0.056* | 0.814 (6) |
O10B | 0.2107 (11) | 0.2438 (6) | 0.2636 (5) | 0.0304 (14)* | 0.186 (6) |
H1OB | 0.3329 (11) | 0.2045 (6) | 0.2876 (5) | 0.046* | 0.186 (6) |
C1B | 0.1502 (4) | 0.2286 (2) | 0.13817 (15) | 0.0476 (4) | |
H11B | 0.1730 (4) | 0.1705 (2) | 0.08402 (15) | 0.141 (13)* | 0.814 (6) |
H12B | 0.2852 (4) | 0.2809 (2) | 0.13298 (15) | 0.141 (13)* | 0.814 (6) |
H13B | −0.0155 (4) | 0.2619 (2) | 0.11740 (15) | 0.141 (13)* | 0.814 (6) |
H14B | 0.1687 (4) | 0.1540 (2) | 0.11895 (15) | 0.212* | 0.186 (6) |
H15B | 0.2665 (4) | 0.2707 (2) | 0.09581 (15) | 0.212* | 0.186 (6) |
H16B | −0.0251 (4) | 0.2511 (2) | 0.11534 (15) | 0.212* | 0.186 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0255 (3) | 0.0216 (3) | 0.0385 (4) | 0.0097 (3) | −0.0121 (3) | −0.0075 (3) |
O2A | 0.0188 (3) | 0.0200 (3) | 0.0414 (4) | 0.0063 (2) | 0.0003 (3) | 0.0045 (3) |
O3A | 0.0169 (3) | 0.0245 (3) | 0.0442 (5) | 0.0053 (2) | 0.0109 (3) | 0.0090 (3) |
N1A | 0.0170 (3) | 0.0170 (3) | 0.0232 (3) | −0.0020 (2) | 0.0003 (2) | −0.0011 (2) |
N2A | 0.0122 (2) | 0.0153 (3) | 0.0249 (3) | 0.0008 (2) | −0.0023 (2) | −0.0022 (2) |
C1A | 0.0141 (3) | 0.0156 (3) | 0.0200 (3) | −0.0008 (2) | −0.0012 (2) | −0.0004 (2) |
C2A | 0.0217 (3) | 0.0247 (4) | 0.0217 (4) | −0.0017 (3) | 0.0015 (3) | 0.0030 (3) |
C3A | 0.0414 (6) | 0.0328 (5) | 0.0260 (5) | −0.0147 (5) | −0.0119 (4) | 0.0081 (4) |
C4A | 0.0293 (6) | 0.0648 (11) | 0.0428 (7) | 0.0100 (6) | −0.0029 (5) | 0.0153 (7) |
C5A | 0.121 (2) | 0.0606 (12) | 0.0222 (6) | 0.0259 (13) | −0.0058 (9) | 0.0002 (7) |
C6A | 0.0135 (3) | 0.0169 (3) | 0.0212 (3) | 0.0015 (2) | −0.0015 (2) | −0.0015 (2) |
C7A | 0.0120 (2) | 0.0167 (3) | 0.0206 (3) | 0.0000 (2) | −0.0008 (2) | −0.0010 (2) |
C8A | 0.0198 (3) | 0.0331 (5) | 0.0204 (4) | −0.0015 (3) | 0.0022 (3) | −0.0040 (3) |
C9A | 0.0388 (6) | 0.0511 (8) | 0.0284 (5) | −0.0057 (6) | 0.0093 (5) | 0.0070 (5) |
C10A | 0.0339 (6) | 0.0623 (10) | 0.0273 (5) | −0.0131 (6) | −0.0028 (4) | −0.0152 (6) |
C11A | 0.0126 (2) | 0.0156 (3) | 0.0214 (3) | 0.0007 (2) | −0.0007 (2) | −0.0001 (2) |
O1B | 0.0223 (5) | 0.0625 (12) | 0.0274 (5) | 0.0139 (6) | 0.0007 (4) | 0.0112 (6) |
C1B | 0.0570 (9) | 0.0516 (9) | 0.0334 (6) | 0.0141 (8) | 0.0002 (6) | 0.0091 (6) |
Geometric parameters (Å, º) top
O1A—C6A | 1.2394 (11) | C5A—H53A | 1.02 (2) |
O2A—C11A | 1.2495 (11) | C7A—C8A | 1.5366 (13) |
O3A—C11A | 1.2599 (11) | C7A—C11A | 1.5454 (12) |
N1A—C1A | 1.4863 (11) | C7A—H71A | 0.91 (2) |
N1A—H1A | 0.87 (2) | C8A—C10A | 1.524 (2) |
N1A—H2A | 0.93 (2) | C8A—C9A | 1.527 (2) |
N1A—H3A | 0.92 (2) | C8A—H81A | 0.96 (2) |
N2A—C6A | 1.3316 (11) | C9A—H91A | 0.970 (14) |
N2A—C7A | 1.4641 (10) | C9A—H92A | 0.970 (14) |
N2A—H4A | 0.81 (2) | C9A—H93A | 0.970 (14) |
C1A—C6A | 1.5292 (11) | C10A—H04A | 0.97 (2) |
C1A—C2A | 1.5380 (13) | C10A—H05A | 0.97 (2) |
C1A—H11A | 0.94 (2) | C10A—H06A | 0.97 (2) |
C2A—C3A | 1.542 (2) | O1B—C1B | 1.384 (2) |
C2A—H21A | 0.978 (14) | O1B—H1B | 0.72 (3) |
C2A—H22A | 0.978 (14) | O1B—H1OB | 0.975 (6) |
C3A—C4A | 1.532 (2) | O10B—C1B | 1.457 (6) |
C3A—C5A | 1.542 (3) | O10B—H1OB | 0.84 |
C3A—H31A | 1.01 (2) | C1B—H11B | 0.98 |
C4A—H41A | 0.97 (2) | C1B—H12B | 0.98 |
C4A—H42A | 0.97 (2) | C1B—H13B | 0.98 |
C4A—H43A | 0.97 (2) | C1B—H14B | 0.98 |
C5A—H51A | 1.02 (2) | C1B—H15B | 0.98 |
C5A—H52A | 1.02 (2) | C1B—H16B | 0.98 |
| | | |
C1A—N1A—H1A | 114.7 (17) | N2A—C7A—C11A | 107.16 (7) |
C1A—N1A—H2A | 106.1 (16) | C8A—C7A—C11A | 112.05 (8) |
H1A—N1A—H2A | 104 (2) | N2A—C7A—H71A | 109.02 (4) |
C1A—N1A—H3A | 106.6 (17) | C8A—C7A—H71A | 109.02 (5) |
H1A—N1A—H3A | 114 (2) | C11A—C7A—H71A | 109.02 (4) |
H2A—N1A—H3A | 112 (2) | C10A—C8A—C9A | 110.99 (12) |
C6A—N2A—C7A | 124.17 (7) | C10A—C8A—C7A | 110.50 (8) |
C6A—N2A—H4A | 121.4 (13) | C9A—C8A—C7A | 110.69 (10) |
C7A—N2A—H4A | 114.4 (13) | C10A—C8A—H81A | 108.18 (9) |
N1A—C1A—C6A | 108.01 (7) | C9A—C8A—H81A | 108.18 (7) |
N1A—C1A—C2A | 110.26 (8) | C7A—C8A—H81A | 108.18 (5) |
C6A—C1A—C2A | 108.99 (7) | C8A—C9A—H91A | 109.47 (7) |
N1A—C1A—H11A | 109.85 (5) | C8A—C9A—H92A | 109.47 (7) |
C6A—C1A—H11A | 109.85 (4) | H91A—C9A—H92A | 109.5 |
C2A—C1A—H11A | 109.85 (5) | C8A—C9A—H93A | 109.47 (7) |
C1A—C2A—C3A | 114.25 (9) | H91A—C9A—H93A | 109.5 |
C1A—C2A—H21A | 108.69 (5) | H92A—C9A—H93A | 109.5 |
C3A—C2A—H21A | 108.69 (6) | C8A—C10A—H04A | 109.47 (9) |
C1A—C2A—H22A | 108.69 (5) | C8A—C10A—H05A | 109.47 (6) |
C3A—C2A—H22A | 108.69 (7) | H04A—C10A—H05A | 109.5 |
H21A—C2A—H22A | 107.6 | C8A—C10A—H06A | 109.47 (9) |
C4A—C3A—C2A | 111.19 (11) | H04A—C10A—H06A | 109.5 |
C4A—C3A—C5A | 110.11 (13) | H05A—C10A—H06A | 109.5 |
C2A—C3A—C5A | 108.59 (15) | O2A—C11A—O3A | 125.37 (9) |
C4A—C3A—H31A | 108.97 (8) | O2A—C11A—C7A | 116.65 (8) |
C2A—C3A—H31A | 108.97 (6) | O3A—C11A—C7A | 117.98 (8) |
C5A—C3A—H31A | 108.97 (12) | C1B—O1B—H1B | 107 (3) |
C3A—C4A—H41A | 109.47 (8) | C1B—O1B—H1OB | 106.6 (4) |
C3A—C4A—H42A | 109.47 (8) | C1B—O10B—H1B | 90 (2) |
H41A—C4A—H42A | 109.5 | C1B—O10B—H1OB | 109.3 (2) |
C3A—C4A—H43A | 109.47 (8) | O1B—C1B—H11B | 109.47 (12) |
H41A—C4A—H43A | 109.5 | O1B—C1B—H12B | 109.47 (12) |
H42A—C4A—H43A | 109.5 | H11B—C1B—H12B | 109.5 |
C3A—C5A—H51A | 109.47 (12) | O1B—C1B—H13B | 109.47 (9) |
C3A—C5A—H52A | 109.47 (12) | H11B—C1B—H13B | 109.5 |
H51A—C5A—H52A | 109.5 | H12B—C1B—H13B | 109.5 |
C3A—C5A—H53A | 109.47 (10) | O10B—C1B—H14B | 109.5 (3) |
H51A—C5A—H53A | 109.5 | O10B—C1B—H15B | 109.5 (3) |
H52A—C5A—H53A | 109.5 | H14B—C1B—H15B | 109.5 |
O1A—C6A—N2A | 125.55 (8) | O10B—C1B—H16B | 109.5 (2) |
O1A—C6A—C1A | 119.98 (8) | H14B—C1B—H16B | 109.5 |
N2A—C6A—C1A | 114.36 (7) | H15B—C1B—H16B | 109.5 |
N2A—C7A—C8A | 110.51 (7) | | |
| | | |
N1A—C1A—C2A—C3A | −73.34 (11) | C6A—N2A—C7A—C8A | 121.13 (10) |
C6A—C1A—C2A—C3A | 168.26 (9) | C6A—N2A—C7A—C11A | −116.54 (9) |
C1A—C2A—C3A—C4A | −78.59 (13) | N2A—C7A—C8A—C10A | 174.33 (11) |
C1A—C2A—C3A—C5A | 160.12 (13) | C11A—C7A—C8A—C10A | 54.91 (13) |
C7A—N2A—C6A—O1A | −6.3 (2) | N2A—C7A—C8A—C9A | −62.30 (11) |
C7A—N2A—C6A—C1A | 169.87 (8) | C11A—C7A—C8A—C9A | 178.28 (9) |
N1A—C1A—C6A—O1A | −30.55 (12) | N2A—C7A—C11A—O2A | −64.79 (10) |
C2A—C1A—C6A—O1A | 89.25 (11) | C8A—C7A—C11A—O2A | 56.58 (11) |
N1A—C1A—C6A—N2A | 153.02 (8) | N2A—C7A—C11A—O3A | 114.57 (9) |
C2A—C1A—C6A—N2A | −87.18 (10) | C8A—C7A—C11A—O3A | −124.06 (9) |
(lve)
L-leucyl-
L-valine ethanol (1:1)
top
Crystal data top
C13H28N2O4 | F(000) = 1216 |
Mr = 276.37 | Dx = 1.156 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0112 (1) Å | Cell parameters from 8192 reflections |
b = 23.5186 (1) Å | µ = 0.09 mm−1 |
c = 12.2636 (1) Å | T = 150 K |
β = 90.0121 (8)° | Block, colourless |
V = 3175.88 (4) Å3 | 0.60 × 0.50 × 0.25 mm |
Z = 8 | |
Data collection top
Siemens SMART CCD diffractometer | 38561 independent reflections |
Radiation source: fine-focus sealed tube | 28178 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Sets of exposures each taken over 0.6° ω rotation scans | θmax = 43.1°, θmin = 1.9° |
Absorption correction: multiscan (SADABS; sheldrick, 1996) ? | h = −21→20 |
Tmin = 0.950, Tmax = 0.979 | k = −44→45 |
50343 measured reflections | l = −23→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)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.144 | Calculated w = 1/[σ2(Fo2) + (0.0434P)2 + 0.3289P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.065 |
38561 reflections | Δρmax = 0.54 e Å−3 |
734 parameters | Δρmin = −0.32 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.24 (45) |
Crystal data top
C13H28N2O4 | V = 3175.88 (4) Å3 |
Mr = 276.37 | Z = 8 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.0112 (1) Å | µ = 0.09 mm−1 |
b = 23.5186 (1) Å | T = 150 K |
c = 12.2636 (1) Å | 0.60 × 0.50 × 0.25 mm |
β = 90.0121 (8)° | |
Data collection top
Siemens SMART CCD diffractometer | 38561 independent reflections |
Absorption correction: multiscan (SADABS; sheldrick, 1996) ? | 28178 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.979 | Rint = 0.039 |
50343 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.144 | Δρmax = 0.54 e Å−3 |
S = 1.07 | Δρmin = −0.32 e Å−3 |
38561 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
734 parameters | Absolute structure parameter: −0.24 (45) |
1 restraint | |
Special details top
Experimental. Normal anistotropic refinement |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement on F2 for ALL reflections. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.09900 (14) | 0.94651 (7) | 0.14833 (14) | 0.0245 (3) | |
O2A | 0.06421 (14) | 0.95806 (8) | −0.20245 (14) | 0.0289 (3) | |
O3A | 0.24732 (11) | 0.93667 (7) | −0.13667 (12) | 0.0224 (3) | |
N1A | −0.09194 (14) | 0.99961 (7) | 0.24707 (12) | 0.0172 (2) | |
H1A | −0.1436 (14) | 1.0265 (6) | 0.2666 (4) | 0.024 (4)* | |
H2A | −0.0181 (13) | 1.0088 (7) | 0.2691 (4) | 0.024 (4)* | |
H3A | −0.1136 (15) | 0.9670 (6) | 0.2773 (5) | 0.024 (4)* | |
N2A | −0.0180 (2) | 0.92152 (9) | 0.0031 (2) | 0.0164 (3) | |
H4A | −0.076 (2) | 0.92140 (9) | −0.0162 (8) | 0.020* | |
C1A | −0.0927 (2) | 0.99360 (8) | 0.1263 (2) | 0.0143 (3) | |
H11A | −0.1744 (2) | 0.98034 (8) | 0.1012 (2) | 0.017* | |
C2A | −0.0622 (2) | 1.05117 (11) | 0.0738 (2) | 0.0179 (4) | |
H21A | 0.0106 (2) | 1.06696 (11) | 0.1102 (2) | 0.021* | |
H22A | −0.0411 (2) | 1.04470 (11) | −0.0037 (2) | 0.021* | |
C3A | −0.1641 (3) | 1.09540 (13) | 0.0793 (2) | 0.0250 (5) | |
H31A | −0.1968 (3) | 1.09577 (13) | 0.1554 (2) | 0.030* | |
C4A | −0.2676 (3) | 1.0818 (2) | 0.0027 (3) | 0.0456 (9) | |
H41A | −0.2969 (16) | 1.0432 (5) | 0.0169 (15) | 0.068* | |
H42A | −0.2391 (7) | 1.0845 (11) | −0.0729 (3) | 0.068* | |
H43A | −0.3339 (10) | 1.1090 (7) | 0.0143 (16) | 0.068* | |
C5A | −0.1122 (4) | 1.15480 (15) | 0.0544 (3) | 0.0398 (8) | |
H51A | −0.0432 (13) | 1.1624 (4) | 0.1027 (13) | 0.060* | |
H52A | −0.1752 (7) | 1.1836 (2) | 0.0662 (18) | 0.060* | |
H53A | −0.0851 (19) | 1.1562 (3) | −0.0217 (6) | 0.060* | |
C6A | 0.0043 (2) | 0.95045 (8) | 0.0942 (2) | 0.0154 (3) | |
C7A | 0.0732 (2) | 0.89021 (10) | −0.0578 (2) | 0.0161 (4) | |
H71A | 0.1362 (2) | 0.87557 (10) | −0.0062 (2) | 0.019* | |
C8A | 0.0137 (3) | 0.83991 (12) | −0.1171 (2) | 0.0210 (5) | |
H81A | −0.0554 (3) | 0.85534 (12) | −0.1609 (2) | 0.025* | |
C9A | −0.0386 (3) | 0.79698 (12) | −0.0367 (3) | 0.0346 (6) | |
H91A | −0.0967 (15) | 0.8161 (2) | 0.0115 (12) | 0.052* | |
H92A | 0.0273 (4) | 0.7806 (7) | 0.0069 (13) | 0.052* | |
H93A | −0.0800 (18) | 0.7666 (5) | −0.0769 (3) | 0.052* | |
C10A | 0.1018 (3) | 0.8117 (2) | −0.1964 (3) | 0.0295 (6) | |
H04A | 0.1349 (15) | 0.8405 (2) | −0.2461 (11) | 0.044* | |
H05A | 0.0588 (6) | 0.7826 (6) | −0.2386 (12) | 0.044* | |
H06A | 0.1683 (11) | 0.7940 (8) | −0.1556 (3) | 0.044* | |
C11A | 0.1331 (2) | 0.93193 (9) | −0.1391 (2) | 0.0162 (3) | |
O1B | 0.5474 (2) | 0.93906 (8) | 0.16286 (14) | 0.0312 (4) | |
O2B | 0.60970 (14) | 0.95462 (8) | −0.18257 (14) | 0.0265 (3) | |
O3B | 0.75266 (13) | 0.91765 (9) | −0.0772 (2) | 0.0404 (4) | |
N1B | 0.35106 (14) | 0.99688 (7) | 0.23991 (13) | 0.0179 (3) | |
H1B | 0.2876 (16) | 1.0172 (7) | 0.2539 (3) | 0.029 (4)* | |
H2B | 0.4140 (13) | 1.0122 (8) | 0.2698 (6) | 0.029 (4)* | |
H3B | 0.3410 (16) | 0.9630 (6) | 0.2656 (5) | 0.029 (4)* | |
N2B | 0.4549 (2) | 0.92255 (9) | −0.0001 (2) | 0.0154 (3) | |
H4B | 0.398 (2) | 0.9266 (2) | −0.0322 (12) | 0.019* | |
C1B | 0.3693 (2) | 0.99374 (8) | 0.1195 (2) | 0.0151 (3) | |
H1CB | 0.2914 (2) | 0.98328 (8) | 0.0827 (2) | 0.018* | |
C2B | 0.4137 (2) | 1.05192 (11) | 0.0782 (2) | 0.0175 (4) | |
H21B | 0.4773 (2) | 1.06625 (11) | 0.1282 (2) | 0.021* | |
H22B | 0.4510 (2) | 1.04697 (11) | 0.0054 (2) | 0.021* | |
C3B | 0.3118 (2) | 1.09652 (12) | 0.0701 (2) | 0.0213 (4) | |
H31B | 0.2591 (2) | 1.09317 (12) | 0.1362 (2) | 0.026* | |
C4B | 0.2333 (3) | 1.08738 (14) | −0.0306 (2) | 0.0274 (5) | |
H41B | 0.1633 (10) | 1.1131 (6) | −0.0281 (8) | 0.041* | |
H42B | 0.2049 (15) | 1.0479 (3) | −0.0324 (9) | 0.041* | |
H43B | 0.2813 (6) | 1.0953 (8) | −0.0962 (2) | 0.041* | |
C5B | 0.3688 (4) | 1.15653 (14) | 0.0687 (3) | 0.0354 (7) | |
H51B | 0.4187 (17) | 1.1618 (4) | 0.1341 (10) | 0.053* | |
H52B | 0.3042 (4) | 1.18518 (14) | 0.0674 (19) | 0.053* | |
H53B | 0.4198 (17) | 1.1607 (4) | 0.0037 (10) | 0.053* | |
C6B | 0.4658 (2) | 0.94861 (8) | 0.0965 (2) | 0.0162 (3) | |
C7B | 0.5503 (2) | 0.88668 (10) | −0.0444 (2) | 0.0142 (3) | |
H71B | 0.5927 (2) | 0.86820 (10) | 0.0184 (2) | 0.017* | |
C8B | 0.4974 (3) | 0.83940 (12) | −0.1157 (2) | 0.0198 (4) | |
H81B | 0.4410 (3) | 0.85731 (12) | −0.1696 (2) | 0.024* | |
C9B | 0.4241 (3) | 0.79782 (13) | −0.0469 (3) | 0.0316 (6) | |
H91B | 0.3934 (16) | 0.7671 (5) | −0.0934 (4) | 0.047* | |
H92B | 0.3557 (11) | 0.8178 (2) | −0.0132 (14) | 0.047* | |
H93B | 0.4761 (6) | 0.7818 (7) | 0.0102 (11) | 0.047* | |
C10B | 0.5969 (4) | 0.8084 (2) | −0.1794 (3) | 0.0314 (7) | |
H04B | 0.6407 (13) | 0.8357 (2) | −0.2253 (13) | 0.047* | |
H05B | 0.5601 (4) | 0.7790 (6) | −0.2254 (13) | 0.047* | |
H06B | 0.6537 (11) | 0.7906 (8) | −0.1281 (3) | 0.047* | |
C11B | 0.6446 (2) | 0.92283 (9) | −0.1059 (2) | 0.0169 (3) | |
O1E | 0.2411 (2) | 0.89284 (9) | 0.3009 (2) | 0.0331 (5) | |
H1E | 0.178 (3) | 0.9052 (17) | 0.271 (3) | 0.050* | |
C1E | 0.2673 (3) | 0.83947 (12) | 0.2513 (3) | 0.0421 (7) | |
H11E | 0.3366 (3) | 0.82159 (12) | 0.2897 (3) | 0.051* | |
H12E | 0.2916 (3) | 0.84578 (12) | 0.1746 (3) | 0.051* | |
C2E | 0.1608 (5) | 0.7999 (2) | 0.2544 (5) | 0.071 (2) | |
H21E | 0.1831 (11) | 0.7636 (5) | 0.221 (3) | 0.107* | |
H22E | 0.0928 (11) | 0.8169 (7) | 0.214 (2) | 0.107* | |
H23E | 0.137 (2) | 0.7934 (12) | 0.3303 (5) | 0.107* | |
O1F | 0.7564 (2) | 0.90558 (9) | 0.2837 (2) | 0.0265 (4) | |
H1F | 0.692 (3) | 0.9185 (15) | 0.272 (3) | 0.040* | |
C1F | 0.7733 (3) | 0.85523 (13) | 0.2178 (3) | 0.0345 (6) | |
H11F | 0.8548 (3) | 0.83914 (13) | 0.2326 (3) | 0.041* | |
H12F | 0.7701 (3) | 0.86593 (13) | 0.1398 (3) | 0.041* | |
C2F | 0.6784 (4) | 0.81042 (14) | 0.2399 (3) | 0.0434 (8) | |
H21F | 0.6971 (14) | 0.7762 (4) | 0.1976 (17) | 0.065* | |
H22F | 0.5983 (5) | 0.8249 (4) | 0.219 (2) | 0.065* | |
H23F | 0.6783 (17) | 0.8011 (8) | 0.3178 (5) | 0.065* | |
O1C | 0.65086 (13) | 0.05474 (7) | 0.64944 (13) | 0.0233 (3) | |
O2C | 0.68550 (14) | 0.04208 (8) | 0.29870 (15) | 0.0278 (3) | |
O3C | 0.50198 (11) | 0.06346 (7) | 0.36361 (12) | 0.0227 (3) | |
N1C | 0.84058 (14) | 0.00070 (7) | 0.74804 (12) | 0.0179 (3) | |
H1C | 0.8986 (18) | −0.0245 (8) | 0.7690 (5) | 0.045 (5)* | |
H2C | 0.7666 (16) | −0.0120 (9) | 0.7699 (5) | 0.045 (5)* | |
H3C | 0.8556 (19) | 0.0351 (7) | 0.7790 (7) | 0.045 (5)* | |
N2C | 0.7678 (2) | 0.07867 (9) | 0.5040 (2) | 0.0161 (3) | |
H4C | 0.843 (2) | 0.07862 (9) | 0.4787 (8) | 0.019* | |
C1C | 0.8421 (2) | 0.00651 (8) | 0.6268 (2) | 0.0147 (3) | |
H11C | 0.9238 (2) | 0.01953 (8) | 0.6016 (2) | 0.018* | |
C2C | 0.8095 (2) | −0.05070 (11) | 0.5736 (2) | 0.0187 (4) | |
H21C | 0.7905 (2) | −0.04394 (11) | 0.4957 (2) | 0.022* | |
H22C | 0.7351 (2) | −0.06562 (11) | 0.6087 (2) | 0.022* | |
C3C | 0.9096 (2) | −0.09655 (11) | 0.5808 (2) | 0.0221 (5) | |
H31C | 0.9400 (2) | −0.09821 (11) | 0.6575 (2) | 0.026* | |
C4C | 1.0152 (3) | −0.08204 (15) | 0.5059 (3) | 0.0455 (9) | |
H41C | 1.0468 (16) | −0.0443 (5) | 0.5246 (15) | 0.068* | |
H42C | 0.9873 (6) | −0.0820 (11) | 0.4300 (4) | 0.068* | |
H43C | 1.0796 (11) | −0.1104 (7) | 0.5148 (17) | 0.068* | |
C5C | 0.8574 (4) | −0.1540 (2) | 0.5509 (3) | 0.0416 (8) | |
H51C | 0.7963 (16) | −0.1651 (5) | 0.6050 (11) | 0.062* | |
H52C | 0.9226 (5) | −0.1824 (2) | 0.5496 (19) | 0.062* | |
H53C | 0.8195 (19) | −0.1518 (3) | 0.4787 (9) | 0.062* | |
C6C | 0.7449 (2) | 0.05019 (8) | 0.59555 (15) | 0.0142 (3) | |
C7C | 0.6754 (2) | 0.11008 (10) | 0.4427 (2) | 0.0141 (3) | |
H71C | 0.6122 (2) | 0.12501 (10) | 0.4938 (2) | 0.017* | |
C8C | 0.7366 (3) | 0.16011 (12) | 0.3817 (2) | 0.0182 (4) | |
H81C | 0.8059 (3) | 0.14473 (12) | 0.3381 (2) | 0.022* | |
C9C | 0.7866 (3) | 0.20363 (12) | 0.4632 (3) | 0.0329 (6) | |
H91C | 0.8303 (17) | 0.2335 (5) | 0.4236 (3) | 0.049* | |
H92C | 0.8422 (15) | 0.1846 (2) | 0.5138 (11) | 0.049* | |
H93C | 0.7193 (3) | 0.2206 (7) | 0.5041 (12) | 0.049* | |
C10C | 0.6476 (3) | 0.18839 (15) | 0.3040 (3) | 0.0298 (6) | |
H04C | 0.6291 (15) | 0.1624 (4) | 0.2438 (9) | 0.045* | |
H05C | 0.6837 (8) | 0.2233 (5) | 0.2749 (14) | 0.045* | |
H06C | 0.5726 (8) | 0.1977 (8) | 0.3432 (5) | 0.045* | |
C11C | 0.6167 (2) | 0.06821 (9) | 0.3613 (2) | 0.0167 (3) | |
O1D | 0.1999 (2) | 0.05945 (8) | 0.65968 (14) | 0.0314 (4) | |
O2D | 0.13878 (13) | 0.04529 (8) | 0.31782 (14) | 0.0260 (3) | |
O3D | −0.00423 (13) | 0.08325 (9) | 0.4221 (2) | 0.0379 (4) | |
N1D | 0.39797 (14) | 0.00299 (7) | 0.73896 (12) | 0.0174 (2) | |
H1D | 0.4656 (15) | −0.0182 (7) | 0.7539 (3) | 0.024 (4)* | |
H2D | 0.3317 (12) | −0.0135 (7) | 0.7709 (6) | 0.024 (4)* | |
H3D | 0.4079 (15) | 0.0389 (6) | 0.7659 (5) | 0.024 (4)* | |
N2D | 0.2948 (2) | 0.07719 (9) | 0.4985 (2) | 0.0153 (3) | |
H4D | 0.3614 (19) | 0.0726 (2) | 0.4610 (11) | 0.018* | |
C1D | 0.3794 (2) | 0.00576 (8) | 0.6180 (2) | 0.0147 (3) | |
H11D | 0.4573 (2) | 0.01643 (8) | 0.5813 (2) | 0.018* | |
C2D | 0.3363 (2) | −0.05240 (11) | 0.5763 (2) | 0.0187 (4) | |
H21D | 0.3010 (2) | −0.04746 (11) | 0.5026 (2) | 0.022* | |
H22D | 0.2709 (2) | −0.06638 (11) | 0.6248 (2) | 0.022* | |
C3D | 0.4366 (2) | −0.09766 (11) | 0.5705 (2) | 0.0203 (4) | |
H31D | 0.4895 (2) | −0.09388 (11) | 0.6364 (2) | 0.024* | |
C4D | 0.5148 (3) | −0.08852 (13) | 0.4685 (2) | 0.0267 (5) | |
H41D | 0.5428 (15) | −0.0490 (2) | 0.4661 (9) | 0.040* | |
H42D | 0.4665 (6) | −0.0967 (8) | 0.4032 (2) | 0.040* | |
H43D | 0.5852 (10) | −0.1140 (6) | 0.4709 (8) | 0.040* | |
C5D | 0.3818 (4) | −0.15675 (15) | 0.5696 (3) | 0.0359 (7) | |
H51D | 0.3410 (18) | −0.1639 (4) | 0.6392 (8) | 0.054* | |
H52D | 0.4463 (4) | −0.1849 (2) | 0.5589 (19) | 0.054* | |
H53D | 0.3228 (16) | −0.1596 (3) | 0.5100 (12) | 0.054* | |
C6D | 0.2828 (2) | 0.05080 (8) | 0.5949 (2) | 0.0160 (3) | |
C7D | 0.1979 (2) | 0.11364 (10) | 0.4547 (2) | 0.0152 (4) | |
H71D | 0.1561 (2) | 0.13255 (10) | 0.5174 (2) | 0.018* | |
C8D | 0.2520 (3) | 0.16030 (12) | 0.3810 (2) | 0.0180 (4) | |
H81D | 0.3065 (3) | 0.14196 (12) | 0.3261 (2) | 0.022* | |
C9D | 0.3275 (2) | 0.20190 (12) | 0.4498 (2) | 0.0292 (5) | |
H91D | 0.3925 (11) | 0.1811 (2) | 0.4871 (13) | 0.044* | |
H92D | 0.2751 (4) | 0.2202 (6) | 0.5040 (11) | 0.044* | |
H93D | 0.3632 (15) | 0.2309 (5) | 0.4023 (3) | 0.044* | |
C10D | 0.1511 (3) | 0.19223 (15) | 0.3205 (3) | 0.0304 (7) | |
H04D | 0.1146 (14) | 0.1671 (3) | 0.2658 (13) | 0.046* | |
H05D | 0.1854 (5) | 0.2257 (5) | 0.2843 (15) | 0.046* | |
H06D | 0.0888 (11) | 0.2043 (8) | 0.3726 (4) | 0.046* | |
C11D | 0.1038 (2) | 0.07731 (9) | 0.3937 (2) | 0.0168 (3) | |
O1G | 0.5025 (2) | 0.10857 (9) | 0.7971 (2) | 0.0368 (5) | |
H1G | 0.558 (4) | 0.0984 (16) | 0.738 (3) | 0.055* | |
C1G | 0.4704 (3) | 0.1593 (2) | 0.7467 (3) | 0.0456 (8) | |
H11G | 0.3992 (3) | 0.1756 (2) | 0.7847 (3) | 0.055* | |
H12G | 0.4462 (3) | 0.1513 (2) | 0.6705 (3) | 0.055* | |
C2G | 0.5711 (5) | 0.2020 (2) | 0.7466 (5) | 0.077 (2) | |
H21G | 0.5471 (15) | 0.2350 (7) | 0.703 (3) | 0.115* | |
H22G | 0.6443 (11) | 0.1849 (5) | 0.715 (3) | 0.115* | |
H23G | 0.588 (2) | 0.2141 (12) | 0.8215 (6) | 0.115* | |
O1H | −0.0060 (2) | 0.09470 (9) | 0.7821 (2) | 0.0275 (4) | |
H1H | 0.047 (3) | 0.0838 (15) | 0.748 (3) | 0.041* | |
C1H | −0.0179 (2) | 0.14497 (11) | 0.7205 (2) | 0.0297 (5) | |
H11H | −0.0983 (2) | 0.16211 (11) | 0.7352 (2) | 0.036* | |
H12H | −0.0140 (2) | 0.13547 (11) | 0.6420 (2) | 0.036* | |
C2H | 0.0804 (3) | 0.18807 (15) | 0.7469 (3) | 0.0432 (8) | |
H21H | 0.0717 (15) | 0.2212 (5) | 0.6991 (15) | 0.065* | |
H22H | 0.1604 (4) | 0.1708 (4) | 0.736 (2) | 0.065* | |
H23H | 0.0727 (15) | 0.2001 (8) | 0.8231 (7) | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0183 (6) | 0.0293 (7) | 0.0258 (7) | 0.0061 (6) | −0.0080 (5) | −0.0055 (6) |
O2A | 0.0175 (6) | 0.0331 (8) | 0.0361 (8) | −0.0005 (6) | −0.0057 (6) | 0.0196 (7) |
O3A | 0.0122 (4) | 0.0319 (7) | 0.0232 (6) | −0.0020 (4) | −0.0023 (4) | 0.0105 (6) |
N1A | 0.0169 (6) | 0.0180 (6) | 0.0168 (6) | 0.0000 (5) | 0.0009 (5) | 0.0020 (6) |
N2A | 0.0115 (6) | 0.0205 (7) | 0.0173 (7) | 0.0030 (6) | −0.0013 (5) | 0.0015 (6) |
C1A | 0.0119 (6) | 0.0168 (7) | 0.0141 (7) | 0.0005 (6) | 0.0008 (5) | 0.0015 (6) |
C2A | 0.0171 (8) | 0.0154 (7) | 0.0212 (8) | −0.0003 (6) | 0.0024 (6) | 0.0047 (7) |
C3A | 0.0292 (11) | 0.0188 (9) | 0.0268 (10) | 0.0051 (8) | 0.0073 (8) | 0.0044 (8) |
C4A | 0.0237 (11) | 0.0338 (14) | 0.079 (3) | 0.0083 (10) | −0.0093 (14) | 0.008 (2) |
C5A | 0.049 (2) | 0.0145 (10) | 0.056 (2) | −0.0006 (10) | −0.0052 (15) | 0.0079 (11) |
C6A | 0.0130 (6) | 0.0148 (7) | 0.0183 (7) | 0.0003 (6) | 0.0008 (6) | 0.0031 (6) |
C7A | 0.0167 (8) | 0.0156 (7) | 0.0160 (8) | 0.0026 (6) | 0.0004 (6) | 0.0025 (6) |
C8A | 0.0212 (9) | 0.0166 (9) | 0.0252 (11) | 0.0002 (7) | 0.0027 (8) | 0.0022 (8) |
C9A | 0.047 (2) | 0.0193 (9) | 0.0375 (14) | −0.0071 (10) | 0.0112 (12) | 0.0016 (9) |
C10A | 0.0306 (13) | 0.0281 (13) | 0.0299 (13) | 0.0035 (10) | 0.0017 (10) | −0.0070 (10) |
C11A | 0.0111 (6) | 0.0190 (8) | 0.0185 (8) | 0.0022 (5) | −0.0019 (6) | 0.0049 (7) |
O1B | 0.0287 (7) | 0.0382 (9) | 0.0268 (8) | 0.0160 (7) | −0.0128 (6) | −0.0103 (7) |
O2B | 0.0187 (6) | 0.0309 (8) | 0.0300 (8) | −0.0005 (6) | 0.0005 (6) | 0.0200 (7) |
O3B | 0.0145 (6) | 0.0572 (11) | 0.0494 (10) | −0.0062 (6) | −0.0090 (6) | 0.0267 (10) |
N1B | 0.0170 (6) | 0.0171 (6) | 0.0195 (7) | 0.0022 (5) | 0.0017 (5) | 0.0026 (6) |
N2B | 0.0135 (7) | 0.0177 (7) | 0.0152 (6) | 0.0019 (5) | −0.0025 (5) | 0.0024 (5) |
C1B | 0.0139 (6) | 0.0148 (6) | 0.0165 (7) | 0.0014 (6) | 0.0003 (6) | 0.0021 (6) |
C2B | 0.0177 (8) | 0.0161 (8) | 0.0188 (8) | −0.0014 (6) | 0.0013 (6) | 0.0058 (7) |
C3B | 0.0239 (10) | 0.0182 (8) | 0.0217 (9) | 0.0015 (7) | 0.0022 (7) | 0.0043 (7) |
C4B | 0.0206 (9) | 0.0307 (11) | 0.0308 (11) | 0.0039 (8) | −0.0017 (8) | 0.0078 (10) |
C5B | 0.050 (2) | 0.0155 (10) | 0.0406 (14) | −0.0029 (10) | −0.0047 (13) | 0.0033 (10) |
C6B | 0.0125 (6) | 0.0178 (7) | 0.0183 (7) | 0.0019 (6) | −0.0024 (6) | 0.0014 (6) |
C7B | 0.0120 (7) | 0.0147 (7) | 0.0160 (8) | 0.0018 (6) | 0.0005 (6) | 0.0032 (6) |
C8B | 0.0215 (9) | 0.0173 (9) | 0.0206 (10) | 0.0005 (7) | 0.0017 (7) | 0.0002 (8) |
C9B | 0.0383 (13) | 0.0223 (10) | 0.0341 (12) | −0.0106 (10) | 0.0080 (11) | 0.0005 (9) |
C10B | 0.0316 (13) | 0.0252 (12) | 0.0373 (15) | 0.0021 (10) | 0.0053 (11) | −0.0075 (11) |
C11B | 0.0118 (6) | 0.0198 (8) | 0.0190 (8) | 0.0012 (5) | −0.0002 (6) | 0.0027 (7) |
O1E | 0.0301 (9) | 0.0289 (9) | 0.0404 (11) | 0.0003 (7) | −0.0071 (8) | 0.0082 (8) |
C1E | 0.0374 (13) | 0.0283 (12) | 0.061 (2) | 0.0008 (10) | −0.0083 (13) | −0.0017 (12) |
C2E | 0.059 (2) | 0.0288 (15) | 0.125 (4) | −0.0128 (14) | −0.031 (2) | 0.001 (2) |
O1F | 0.0201 (7) | 0.0253 (8) | 0.0340 (9) | −0.0004 (6) | −0.0034 (6) | 0.0061 (7) |
C1F | 0.0269 (10) | 0.0401 (14) | 0.0365 (13) | 0.0009 (9) | −0.0006 (9) | 0.0028 (11) |
C2F | 0.052 (2) | 0.0246 (12) | 0.053 (2) | −0.0087 (11) | −0.0056 (14) | 0.0104 (12) |
O1C | 0.0179 (5) | 0.0275 (7) | 0.0245 (7) | 0.0063 (5) | 0.0070 (5) | 0.0132 (6) |
O2C | 0.0175 (6) | 0.0311 (8) | 0.0349 (8) | −0.0012 (6) | 0.0057 (6) | −0.0107 (7) |
O3C | 0.0125 (5) | 0.0323 (7) | 0.0234 (6) | −0.0014 (4) | 0.0019 (4) | −0.0014 (6) |
N1C | 0.0182 (6) | 0.0200 (6) | 0.0155 (6) | 0.0011 (5) | −0.0013 (5) | 0.0081 (6) |
N2C | 0.0123 (6) | 0.0196 (7) | 0.0163 (6) | 0.0023 (6) | 0.0011 (5) | 0.0092 (5) |
C1C | 0.0142 (6) | 0.0154 (7) | 0.0146 (7) | 0.0006 (6) | −0.0011 (6) | 0.0051 (6) |
C2C | 0.0176 (9) | 0.0180 (8) | 0.0206 (8) | −0.0001 (7) | −0.0033 (7) | 0.0047 (7) |
C3C | 0.0267 (11) | 0.0159 (8) | 0.0235 (9) | 0.0051 (7) | −0.0056 (8) | 0.0031 (7) |
C4C | 0.0252 (11) | 0.0308 (14) | 0.080 (3) | 0.0076 (9) | 0.0140 (15) | 0.006 (2) |
C5C | 0.053 (2) | 0.0197 (12) | 0.053 (2) | 0.0011 (11) | 0.003 (2) | −0.0003 (12) |
C6C | 0.0127 (6) | 0.0149 (6) | 0.0151 (7) | 0.0008 (6) | −0.0011 (6) | 0.0059 (6) |
C7C | 0.0101 (6) | 0.0170 (7) | 0.0150 (7) | 0.0021 (5) | −0.0007 (5) | 0.0065 (6) |
C8C | 0.0213 (9) | 0.0153 (8) | 0.0181 (9) | 0.0005 (7) | 0.0000 (7) | 0.0073 (7) |
C9C | 0.045 (2) | 0.0193 (9) | 0.0344 (12) | −0.0056 (10) | −0.0110 (12) | 0.0043 (9) |
C10C | 0.0341 (14) | 0.0243 (12) | 0.0312 (13) | 0.0018 (10) | −0.0082 (10) | 0.0166 (10) |
C11C | 0.0145 (6) | 0.0166 (8) | 0.0189 (9) | −0.0006 (5) | −0.0004 (6) | 0.0058 (7) |
O1D | 0.0281 (7) | 0.0359 (9) | 0.0302 (8) | 0.0157 (7) | 0.0162 (7) | 0.0193 (7) |
O2D | 0.0162 (6) | 0.0312 (8) | 0.0306 (8) | 0.0002 (5) | 0.0003 (6) | −0.0085 (7) |
O3D | 0.0132 (5) | 0.0546 (11) | 0.0460 (10) | −0.0033 (6) | 0.0076 (6) | −0.0172 (9) |
N1D | 0.0176 (6) | 0.0178 (6) | 0.0170 (6) | 0.0016 (5) | −0.0001 (5) | 0.0050 (5) |
N2D | 0.0119 (6) | 0.0178 (7) | 0.0160 (6) | 0.0032 (5) | 0.0026 (5) | 0.0072 (5) |
C1D | 0.0129 (6) | 0.0148 (6) | 0.0164 (7) | 0.0012 (6) | 0.0010 (6) | 0.0059 (6) |
C2D | 0.0150 (8) | 0.0177 (8) | 0.0235 (9) | 0.0004 (6) | 0.0004 (6) | 0.0050 (7) |
C3D | 0.0246 (10) | 0.0132 (8) | 0.0232 (9) | 0.0044 (7) | −0.0030 (7) | 0.0034 (7) |
C4D | 0.0230 (9) | 0.0253 (11) | 0.0318 (11) | 0.0042 (8) | 0.0020 (8) | −0.0005 (9) |
C5D | 0.044 (2) | 0.0187 (11) | 0.045 (2) | −0.0011 (10) | −0.0003 (13) | 0.0027 (11) |
C6D | 0.0151 (7) | 0.0155 (7) | 0.0173 (7) | 0.0012 (6) | 0.0027 (6) | 0.0062 (6) |
C7D | 0.0153 (7) | 0.0153 (8) | 0.0150 (8) | 0.0025 (6) | 0.0018 (6) | 0.0045 (6) |
C8D | 0.0195 (9) | 0.0167 (9) | 0.0177 (9) | 0.0005 (7) | 0.0018 (7) | 0.0075 (7) |
C9D | 0.0328 (12) | 0.0206 (9) | 0.0341 (12) | −0.0084 (9) | −0.0030 (10) | 0.0058 (9) |
C10D | 0.0339 (14) | 0.0217 (11) | 0.0356 (14) | 0.0030 (10) | −0.0093 (11) | 0.0140 (10) |
C11D | 0.0129 (6) | 0.0179 (8) | 0.0196 (8) | 0.0012 (5) | 0.0024 (6) | 0.0062 (7) |
O1G | 0.0317 (9) | 0.0249 (9) | 0.0538 (13) | −0.0002 (7) | 0.0129 (9) | 0.0018 (9) |
C1G | 0.0374 (14) | 0.047 (2) | 0.053 (2) | −0.0031 (12) | 0.0042 (13) | 0.0169 (15) |
C2G | 0.068 (2) | 0.034 (2) | 0.128 (4) | −0.015 (2) | 0.048 (3) | −0.008 (2) |
O1H | 0.0220 (7) | 0.0276 (9) | 0.0329 (9) | 0.0013 (6) | 0.0036 (6) | −0.0016 (7) |
C1H | 0.0245 (9) | 0.0283 (11) | 0.0362 (12) | 0.0038 (8) | −0.0001 (8) | 0.0044 (10) |
C2H | 0.0413 (15) | 0.0296 (14) | 0.059 (2) | −0.0041 (11) | 0.0046 (13) | 0.0069 (13) |
Geometric parameters (Å, º) top
O1A—C6A | 1.240 (2) | O1C—C6C | 1.233 (2) |
O2A—C11A | 1.248 (2) | O2C—C11C | 1.241 (3) |
O3A—C11A | 1.263 (2) | O3C—C11C | 1.269 (2) |
N1A—C1A | 1.488 (2) | N1C—C1C | 1.493 (2) |
N1A—H1A | 0.884 (15) | N1C—H1C | 0.91 (2) |
N1A—H2A | 0.88 (2) | N1C—H2C | 0.91 (2) |
N1A—H3A | 0.884 (15) | N1C—H3C | 0.91 (2) |
N2A—C6A | 1.331 (3) | N2C—C6C | 1.332 (3) |
N2A—C7A | 1.451 (3) | N2C—C7C | 1.465 (3) |
N2A—H4A | 0.68 (3) | N2C—H4C | 0.89 (3) |
C1A—C6A | 1.525 (3) | C1C—C6C | 1.532 (2) |
C1A—C2A | 1.537 (3) | C1C—C2C | 1.538 (3) |
C1A—H11A | 1.00 | C1C—H11C | 1.00 |
C2A—C3A | 1.532 (4) | C2C—C3C | 1.544 (3) |
C2A—H21A | 0.99 | C2C—H21C | 0.99 |
C2A—H22A | 0.99 | C2C—H22C | 0.99 |
C3A—C4A | 1.511 (5) | C3C—C5C | 1.514 (5) |
C3A—C5A | 1.540 (5) | C3C—C4C | 1.521 (4) |
C3A—H31A | 1.00 | C3C—H31C | 1.00 |
C4A—H41A | 0.98 | C4C—H41C | 0.98 |
C4A—H42A | 0.98 | C4C—H42C | 0.98 |
C4A—H43A | 0.98 | C4C—H43C | 0.98 |
C5A—H51A | 0.98 | C5C—H51C | 0.98 |
C5A—H52A | 0.98 | C5C—H52C | 0.98 |
C5A—H53A | 0.98 | C5C—H53C | 0.98 |
C7A—C8A | 1.535 (4) | C7C—C11C | 1.544 (3) |
C7A—C11A | 1.547 (3) | C7C—C8C | 1.548 (3) |
C7A—H71A | 1.00 | C7C—H71C | 1.00 |
C8A—C10A | 1.525 (4) | C8C—C10C | 1.520 (4) |
C8A—C9A | 1.524 (4) | C8C—C9C | 1.532 (4) |
C8A—H81A | 1.00 | C8C—H81C | 1.00 |
C9A—H91A | 0.98 | C9C—H91C | 0.98 |
C9A—H92A | 0.98 | C9C—H92C | 0.98 |
C9A—H93A | 0.98 | C9C—H93C | 0.98 |
C10A—H04A | 0.98 | C10C—H04C | 0.98 |
C10A—H05A | 0.98 | C10C—H05C | 0.98 |
C10A—H06A | 0.98 | C10C—H06C | 0.98 |
O1B—C6B | 1.233 (2) | O1D—C6D | 1.228 (2) |
O2B—C11B | 1.261 (2) | O2D—C11D | 1.257 (3) |
O3B—C11B | 1.247 (2) | O3D—C11D | 1.247 (2) |
N1B—C1B | 1.492 (2) | N1D—C1D | 1.499 (2) |
N1B—H1B | 0.86 (2) | N1D—H1D | 0.91 (2) |
N1B—H2B | 0.86 (2) | N1D—H2D | 0.91 (2) |
N1B—H3B | 0.86 (2) | N1D—H3D | 0.91 (2) |
N2B—C6B | 1.340 (3) | N2D—C6D | 1.342 (3) |
N2B—C7B | 1.453 (3) | N2D—C7D | 1.471 (3) |
N2B—H4B | 0.75 (3) | N2D—H4D | 0.87 (2) |
C1B—C6B | 1.528 (3) | C1D—C6D | 1.527 (2) |
C1B—C2B | 1.538 (3) | C1D—C2D | 1.536 (3) |
C1B—H1CB | 1.00 | C1D—H11D | 1.00 |
C2B—C3B | 1.539 (3) | C2D—C3D | 1.536 (3) |
C2B—H21B | 0.99 | C2D—H21D | 0.99 |
C2B—H22B | 0.99 | C2D—H22D | 0.99 |
C3B—C4B | 1.523 (4) | C3D—C5D | 1.515 (5) |
C3B—C5B | 1.545 (4) | C3D—C4D | 1.534 (4) |
C3B—H31B | 1.00 | C3D—H31D | 1.00 |
C4B—H41B | 0.98 | C4D—H41D | 0.98 |
C4B—H42B | 0.98 | C4D—H42D | 0.98 |
C4B—H43B | 0.98 | C4D—H43D | 0.98 |
C5B—H51B | 0.98 | C5D—H51D | 0.98 |
C5B—H52B | 0.98 | C5D—H52D | 0.98 |
C5B—H53B | 0.98 | C5D—H53D | 0.98 |
C7B—C8B | 1.530 (4) | C7D—C11D | 1.537 (3) |
C7B—C11B | 1.539 (3) | C7D—C8D | 1.542 (3) |
C7B—H71B | 1.00 | C7D—H71D | 1.00 |
C8B—C9B | 1.523 (4) | C8D—C9D | 1.537 (4) |
C8B—C10B | 1.531 (4) | C8D—C10D | 1.533 (4) |
C8B—H81B | 1.00 | C8D—H81D | 1.00 |
C9B—H91B | 0.98 | C9D—H91D | 0.98 |
C9B—H92B | 0.98 | C9D—H92D | 0.98 |
C9B—H93B | 0.98 | C9D—H93D | 0.98 |
C10B—H04B | 0.98 | C10D—H04D | 0.98 |
C10B—H05B | 0.98 | C10D—H05D | 0.98 |
C10B—H06B | 0.98 | C10D—H06D | 0.98 |
O1E—C1E | 1.424 (4) | O1G—C1G | 1.389 (4) |
O1E—H1E | 0.83 (4) | O1G—H1G | 0.98 (4) |
C1E—C2E | 1.498 (5) | C1G—C2G | 1.497 (6) |
C1E—H11E | 0.99 | C1G—H11G | 0.99 |
C1E—H12E | 0.99 | C1G—H12G | 0.99 |
C2E—H21E | 0.98 | C2G—H21G | 0.98 |
C2E—H22E | 0.98 | C2G—H22G | 0.98 |
C2E—H23E | 0.98 | C2G—H23G | 0.98 |
O1F—C1F | 1.446 (4) | O1H—C1H | 1.409 (3) |
O1F—H1F | 0.79 (4) | O1H—H1H | 0.76 (4) |
C1F—C2F | 1.509 (4) | C1H—C2H | 1.518 (4) |
C1F—H11F | 0.99 | C1H—H11H | 0.99 |
C1F—H12F | 0.99 | C1H—H12H | 0.99 |
C2F—H21F | 0.98 | C2H—H21H | 0.98 |
C2F—H22F | 0.98 | C2H—H22H | 0.98 |
C2F—H23F | 0.98 | C2H—H23H | 0.98 |
| | | |
C1A—N1A—H1A | 109.47 (9) | C1C—N1C—H1C | 109.47 (10) |
C1A—N1A—H2A | 109.47 (9) | C1C—N1C—H2C | 109.47 (9) |
H1A—N1A—H2A | 109.5 | H1C—N1C—H2C | 109.5 |
C1A—N1A—H3A | 109.47 (10) | C1C—N1C—H3C | 109.47 (10) |
H1A—N1A—H3A | 109.5 | H1C—N1C—H3C | 109.5 |
H2A—N1A—H3A | 109.5 | H2C—N1C—H3C | 109.5 |
C6A—N2A—C7A | 124.3 (2) | C6C—N2C—C7C | 123.6 (2) |
C6A—N2A—H4A | 117.85 (11) | C6C—N2C—H4C | 118.18 (11) |
C7A—N2A—H4A | 117.85 (12) | C7C—N2C—H4C | 118.18 (11) |
N1A—C1A—C6A | 108.42 (15) | N1C—C1C—C6C | 107.63 (15) |
N1A—C1A—C2A | 109.4 (2) | N1C—C1C—C2C | 109.9 (2) |
C6A—C1A—C2A | 109.0 (2) | C6C—C1C—C2C | 108.5 (2) |
N1A—C1A—H11A | 110.01 (9) | N1C—C1C—H11C | 110.25 (9) |
C6A—C1A—H11A | 110.01 (10) | C6C—C1C—H11C | 110.25 (9) |
C2A—C1A—H11A | 110.01 (11) | C2C—C1C—H11C | 110.25 (11) |
C3A—C2A—C1A | 114.8 (2) | C1C—C2C—C3C | 114.9 (2) |
C3A—C2A—H21A | 108.6 (2) | C1C—C2C—H21C | 108.55 (11) |
C1A—C2A—H21A | 108.57 (11) | C3C—C2C—H21C | 108.55 (14) |
C3A—C2A—H22A | 108.6 (2) | C1C—C2C—H22C | 108.55 (12) |
C1A—C2A—H22A | 108.57 (12) | C3C—C2C—H22C | 108.55 (14) |
H21A—C2A—H22A | 107.5 | H21C—C2C—H22C | 107.5 |
C4A—C3A—C2A | 112.4 (3) | C5C—C3C—C4C | 110.2 (3) |
C4A—C3A—C5A | 110.4 (3) | C5C—C3C—C2C | 109.8 (2) |
C2A—C3A—C5A | 109.6 (3) | C4C—C3C—C2C | 110.8 (2) |
C4A—C3A—H31A | 108.1 (2) | C5C—C3C—H31C | 108.7 (2) |
C2A—C3A—H31A | 108.1 (2) | C4C—C3C—H31C | 108.7 (2) |
C5A—C3A—H31A | 108.1 (2) | C2C—C3C—H31C | 108.69 (14) |
C3A—C4A—H41A | 109.5 (2) | C3C—C4C—H41C | 109.5 (2) |
C3A—C4A—H42A | 109.5 (2) | C3C—C4C—H42C | 109.5 (2) |
H41A—C4A—H42A | 109.5 | H41C—C4C—H42C | 109.5 |
C3A—C4A—H43A | 109.5 (2) | C3C—C4C—H43C | 109.5 (2) |
H41A—C4A—H43A | 109.5 | H41C—C4C—H43C | 109.5 |
H42A—C4A—H43A | 109.5 | H42C—C4C—H43C | 109.5 |
C3A—C5A—H51A | 109.5 (2) | C3C—C5C—H51C | 109.5 (2) |
C3A—C5A—H52A | 109.5 (2) | C3C—C5C—H52C | 109.5 (2) |
H51A—C5A—H52A | 109.5 | H51C—C5C—H52C | 109.5 |
C3A—C5A—H53A | 109.5 (2) | C3C—C5C—H53C | 109.5 (2) |
H51A—C5A—H53A | 109.5 | H51C—C5C—H53C | 109.5 |
H52A—C5A—H53A | 109.5 | H52C—C5C—H53C | 109.5 |
O1A—C6A—N2A | 124.5 (2) | O1C—C6C—N2C | 124.6 (2) |
O1A—C6A—C1A | 120.1 (2) | O1C—C6C—C1C | 120.7 (2) |
N2A—C6A—C1A | 115.3 (2) | N2C—C6C—C1C | 114.5 (2) |
N2A—C7A—C8A | 109.9 (2) | N2C—C7C—C11C | 107.5 (2) |
N2A—C7A—C11A | 107.7 (2) | N2C—C7C—C8C | 109.2 (2) |
C8A—C7A—C11A | 111.4 (2) | C11C—C7C—C8C | 110.8 (2) |
N2A—C7A—H71A | 109.27 (12) | N2C—C7C—H71C | 109.78 (12) |
C8A—C7A—H71A | 109.26 (14) | C11C—C7C—H71C | 109.78 (11) |
C11A—C7A—H71A | 109.26 (11) | C8C—C7C—H71C | 109.78 (14) |
C10A—C8A—C9A | 111.4 (3) | C10C—C8C—C9C | 110.4 (3) |
C10A—C8A—C7A | 111.5 (2) | C10C—C8C—C7C | 110.8 (2) |
C9A—C8A—C7A | 111.4 (2) | C9C—C8C—C7C | 110.4 (2) |
C10A—C8A—H81A | 107.4 (2) | C10C—C8C—H81C | 108.4 (2) |
C9A—C8A—H81A | 107.4 (2) | C9C—C8C—H81C | 108.4 (2) |
C7A—C8A—H81A | 107.43 (14) | C7C—C8C—H81C | 108.38 (13) |
C8A—C9A—H91A | 109.5 (2) | C8C—C9C—H91C | 109.5 (2) |
C8A—C9A—H92A | 109.5 (2) | C8C—C9C—H92C | 109.47 (15) |
H91A—C9A—H92A | 109.5 | H91C—C9C—H92C | 109.5 |
C8A—C9A—H93A | 109.5 (2) | C8C—C9C—H93C | 109.5 (2) |
H91A—C9A—H93A | 109.5 | H91C—C9C—H93C | 109.5 |
H92A—C9A—H93A | 109.5 | H92C—C9C—H93C | 109.5 |
C8A—C10A—H04A | 109.5 (2) | C8C—C10C—H04C | 109.5 (2) |
C8A—C10A—H05A | 109.5 (2) | C8C—C10C—H05C | 109.5 (2) |
H04A—C10A—H05A | 109.5 | H04C—C10C—H05C | 109.5 |
C8A—C10A—H06A | 109.5 (2) | C8C—C10C—H06C | 109.5 (2) |
H04A—C10A—H06A | 109.5 | H04C—C10C—H06C | 109.5 |
H05A—C10A—H06A | 109.5 | H05C—C10C—H06C | 109.5 |
O2A—C11A—O3A | 125.2 (2) | O2C—C11C—O3C | 125.3 (2) |
O2A—C11A—C7A | 117.1 (2) | O2C—C11C—C7C | 117.4 (2) |
O3A—C11A—C7A | 117.8 (2) | O3C—C11C—C7C | 117.3 (2) |
C1B—N1B—H1B | 109.47 (9) | C1D—N1D—H1D | 109.47 (9) |
C1B—N1B—H2B | 109.47 (10) | C1D—N1D—H2D | 109.47 (9) |
H1B—N1B—H2B | 109.5 | H1D—N1D—H2D | 109.5 |
C1B—N1B—H3B | 109.47 (10) | C1D—N1D—H3D | 109.47 (10) |
H1B—N1B—H3B | 109.5 | H1D—N1D—H3D | 109.5 |
H2B—N1B—H3B | 109.5 | H2D—N1D—H3D | 109.5 |
C6B—N2B—C7B | 122.1 (2) | C6D—N2D—C7D | 121.3 (2) |
C6B—N2B—H4B | 118.95 (11) | C6D—N2D—H4D | 119.33 (11) |
C7B—N2B—H4B | 118.95 (12) | C7D—N2D—H4D | 119.33 (11) |
N1B—C1B—C6B | 108.08 (15) | N1D—C1D—C6D | 108.0 (2) |
N1B—C1B—C2B | 108.9 (2) | N1D—C1D—C2D | 109.5 (2) |
C6B—C1B—C2B | 109.7 (2) | C6D—C1D—C2D | 109.9 (2) |
N1B—C1B—H1CB | 110.05 (9) | N1D—C1D—H11D | 109.82 (9) |
C6B—C1B—H1CB | 110.05 (10) | C6D—C1D—H11D | 109.82 (10) |
C2B—C1B—H1CB | 110.05 (11) | C2D—C1D—H11D | 109.82 (11) |
C3B—C2B—C1B | 113.3 (2) | C1D—C2D—C3D | 114.2 (2) |
C3B—C2B—H21B | 108.91 (14) | C1D—C2D—H21D | 108.70 (12) |
C1B—C2B—H21B | 108.91 (12) | C3D—C2D—H21D | 108.71 (15) |
C3B—C2B—H22B | 108.90 (14) | C1D—C2D—H22D | 108.70 (12) |
C1B—C2B—H22B | 108.91 (12) | C3D—C2D—H22D | 108.70 (14) |
H21B—C2B—H22B | 107.7 | H21D—C2D—H22D | 107.6 |
C4B—C3B—C2B | 111.7 (2) | C5D—C3D—C4D | 110.3 (3) |
C4B—C3B—C5B | 110.5 (2) | C5D—C3D—C2D | 110.4 (2) |
C2B—C3B—C5B | 109.1 (2) | C4D—C3D—C2D | 110.2 (2) |
C4B—C3B—H31B | 108.47 (15) | C5D—C3D—H31D | 108.6 (2) |
C2B—C3B—H31B | 108.47 (14) | C4D—C3D—H31D | 108.64 (15) |
C5B—C3B—H31B | 108.5 (2) | C2D—C3D—H31D | 108.64 (15) |
C3B—C4B—H41B | 109.5 (2) | C3D—C4D—H41D | 109.5 (2) |
C3B—C4B—H42B | 109.5 (2) | C3D—C4D—H42D | 109.47 (15) |
H41B—C4B—H42B | 109.5 | H41D—C4D—H42D | 109.5 |
C3B—C4B—H43B | 109.47 (15) | C3D—C4D—H43D | 109.47 (14) |
H41B—C4B—H43B | 109.5 | H41D—C4D—H43D | 109.5 |
H42B—C4B—H43B | 109.5 | H42D—C4D—H43D | 109.5 |
C3B—C5B—H51B | 109.5 (2) | C3D—C5D—H51D | 109.5 (2) |
C3B—C5B—H52B | 109.5 (2) | C3D—C5D—H52D | 109.5 (2) |
H51B—C5B—H52B | 109.5 | H51D—C5D—H52D | 109.5 |
C3B—C5B—H53B | 109.5 (2) | C3D—C5D—H53D | 109.5 (2) |
H51B—C5B—H53B | 109.5 | H51D—C5D—H53D | 109.5 |
H52B—C5B—H53B | 109.5 | H52D—C5D—H53D | 109.5 |
O1B—C6B—N2B | 124.5 (2) | O1D—C6D—N2D | 124.5 (2) |
O1B—C6B—C1B | 120.8 (2) | O1D—C6D—C1D | 120.8 (2) |
N2B—C6B—C1B | 114.7 (2) | N2D—C6D—C1D | 114.6 (2) |
N2B—C7B—C8B | 111.1 (2) | N2D—C7D—C11D | 110.1 (2) |
N2B—C7B—C11B | 110.5 (2) | N2D—C7D—C8D | 110.4 (2) |
C8B—C7B—C11B | 112.2 (2) | C11D—C7D—C8D | 111.8 (2) |
N2B—C7B—H71B | 107.60 (12) | N2D—C7D—H71D | 108.17 (12) |
C8B—C7B—H71B | 107.60 (13) | C11D—C7D—H71D | 108.17 (11) |
C11B—C7B—H71B | 107.60 (10) | C8D—C7D—H71D | 108.17 (14) |
C9B—C8B—C10B | 110.9 (3) | C9D—C8D—C10D | 110.3 (3) |
C9B—C8B—C7B | 110.6 (2) | C9D—C8D—C7D | 109.9 (2) |
C10B—C8B—C7B | 111.4 (2) | C10D—C8D—C7D | 110.6 (2) |
C9B—C8B—H81B | 107.9 (2) | C9D—C8D—H81D | 108.7 (2) |
C10B—C8B—H81B | 107.9 (2) | C10D—C8D—H81D | 108.7 (2) |
C7B—C8B—H81B | 107.94 (14) | C7D—C8D—H81D | 108.66 (14) |
C8B—C9B—H91B | 109.5 (2) | C8D—C9D—H91D | 109.5 (2) |
C8B—C9B—H92B | 109.5 (2) | C8D—C9D—H92D | 109.47 (15) |
H91B—C9B—H92B | 109.5 | H91D—C9D—H92D | 109.5 |
C8B—C9B—H93B | 109.5 (2) | C8D—C9D—H93D | 109.47 (15) |
H91B—C9B—H93B | 109.5 | H91D—C9D—H93D | 109.5 |
H92B—C9B—H93B | 109.5 | H92D—C9D—H93D | 109.5 |
C8B—C10B—H04B | 109.5 (2) | C8D—C10D—H04D | 109.5 (2) |
C8B—C10B—H05B | 109.5 (2) | C8D—C10D—H05D | 109.5 (2) |
H04B—C10B—H05B | 109.5 | H04D—C10D—H05D | 109.5 |
C8B—C10B—H06B | 109.5 (2) | C8D—C10D—H06D | 109.5 (2) |
H04B—C10B—H06B | 109.5 | H04D—C10D—H06D | 109.5 |
H05B—C10B—H06B | 109.5 | H05D—C10D—H06D | 109.5 |
O3B—C11B—O2B | 124.0 (2) | O3D—C11D—O2D | 124.5 (2) |
O3B—C11B—C7B | 116.8 (2) | O3D—C11D—C7D | 116.4 (2) |
O2B—C11B—C7B | 119.2 (2) | O2D—C11D—C7D | 119.1 (2) |
C1E—O1E—H1E | 107 (3) | C1G—O1G—H1G | 92 (2) |
O1E—C1E—C2E | 112.2 (3) | O1G—C1G—C2G | 112.9 (4) |
O1E—C1E—H11E | 109.2 (2) | O1G—C1G—H11G | 109.0 (2) |
C2E—C1E—H11E | 109.2 (2) | C2G—C1G—H11G | 109.0 (2) |
O1E—C1E—H12E | 109.2 (2) | O1G—C1G—H12G | 109.0 (2) |
C2E—C1E—H12E | 109.2 (3) | C2G—C1G—H12G | 109.0 (3) |
H11E—C1E—H12E | 107.9 | H11G—C1G—H12G | 107.8 |
C1E—C2E—H21E | 109.5 (3) | C1G—C2G—H21G | 109.5 (3) |
C1E—C2E—H22E | 109.5 (2) | C1G—C2G—H22G | 109.5 (2) |
H21E—C2E—H22E | 109.5 | H21G—C2G—H22G | 109.5 |
C1E—C2E—H23E | 109.5 (3) | C1G—C2G—H23G | 109.5 (3) |
H21E—C2E—H23E | 109.5 | H21G—C2G—H23G | 109.5 |
H22E—C2E—H23E | 109.5 | H22G—C2G—H23G | 109.5 |
C1F—O1F—H1F | 109 (2) | C1H—O1H—H1H | 94 (3) |
O1F—C1F—C2F | 112.5 (3) | O1H—C1H—C2H | 112.3 (2) |
O1F—C1F—H11F | 109.10 (14) | O1H—C1H—H11H | 109.13 (14) |
C2F—C1F—H11F | 109.1 (2) | C2H—C1H—H11H | 109.1 (2) |
O1F—C1F—H12F | 109.10 (14) | O1H—C1H—H12H | 109.13 (14) |
C2F—C1F—H12F | 109.1 (2) | C2H—C1H—H12H | 109.1 (2) |
H11F—C1F—H12F | 107.8 | H11H—C1H—H12H | 107.9 |
C1F—C2F—H21F | 109.5 (2) | C1H—C2H—H21H | 109.5 (2) |
C1F—C2F—H22F | 109.5 (2) | C1H—C2H—H22H | 109.5 (2) |
H21F—C2F—H22F | 109.5 | H21H—C2H—H22H | 109.5 |
C1F—C2F—H23F | 109.5 (2) | C1H—C2H—H23H | 109.5 (2) |
H21F—C2F—H23F | 109.5 | H21H—C2H—H23H | 109.5 |
H22F—C2F—H23F | 109.5 | H22H—C2H—H23H | 109.5 |
| | | |
N1A—C1A—C2A—C3A | −73.5 (3) | N1C—C1C—C2C—C3C | −72.5 (2) |
C6A—C1A—C2A—C3A | 168.2 (2) | C6C—C1C—C2C—C3C | 170.0 (2) |
C1A—C2A—C3A—C4A | −72.6 (3) | C1C—C2C—C3C—C5C | 166.5 (2) |
C1A—C2A—C3A—C5A | 164.2 (3) | C1C—C2C—C3C—C4C | −71.6 (3) |
C7A—N2A—C6A—O1A | −12.9 (3) | C7C—N2C—C6C—O1C | −13.3 (4) |
C7A—N2A—C6A—C1A | 162.9 (2) | C7C—N2C—C6C—C1C | 162.3 (2) |
N1A—C1A—C6A—O1A | −33.0 (2) | N1C—C1C—C6C—O1C | −32.7 (2) |
C2A—C1A—C6A—O1A | 86.0 (2) | C2C—C1C—C6C—O1C | 86.2 (2) |
N1A—C1A—C6A—N2A | 151.0 (2) | N1C—C1C—C6C—N2C | 151.5 (2) |
C2A—C1A—C6A—N2A | −90.0 (2) | C2C—C1C—C6C—N2C | −89.6 (2) |
C6A—N2A—C7A—C8A | 150.9 (2) | C6C—N2C—C7C—C11C | −88.4 (3) |
C6A—N2A—C7A—C11A | −87.6 (3) | C6C—N2C—C7C—C8C | 151.3 (2) |
N2A—C7A—C8A—C10A | 170.7 (2) | N2C—C7C—C8C—C10C | 171.5 (2) |
C11A—C7A—C8A—C10A | 51.4 (3) | C11C—C7C—C8C—C10C | 53.3 (3) |
N2A—C7A—C8A—C9A | −64.1 (3) | N2C—C7C—C8C—C9C | −65.8 (3) |
C11A—C7A—C8A—C9A | 176.5 (2) | C11C—C7C—C8C—C9C | 175.9 (2) |
N2A—C7A—C11A—O2A | −54.8 (3) | N2C—C7C—C11C—O2C | −54.2 (2) |
C8A—C7A—C11A—O2A | 65.7 (3) | C8C—C7C—C11C—O2C | 65.0 (3) |
N2A—C7A—C11A—O3A | 125.6 (2) | N2C—C7C—C11C—O3C | 126.0 (2) |
C8A—C7A—C11A—O3A | −113.9 (2) | C8C—C7C—C11C—O3C | −114.8 (2) |
N1B—C1B—C2B—C3B | −76.9 (2) | N1D—C1D—C2D—C3D | −75.3 (2) |
C6B—C1B—C2B—C3B | 165.0 (2) | C6D—C1D—C2D—C3D | 166.3 (2) |
C1B—C2B—C3B—C4B | −77.4 (3) | C1D—C2D—C3D—C5D | 159.3 (2) |
C1B—C2B—C3B—C5B | 160.0 (2) | C1D—C2D—C3D—C4D | −78.7 (3) |
C7B—N2B—C6B—O1B | −10.3 (3) | C7D—N2D—C6D—O1D | −9.0 (4) |
C7B—N2B—C6B—C1B | 168.1 (2) | C7D—N2D—C6D—C1D | 168.4 (2) |
N1B—C1B—C6B—O1B | −30.4 (3) | N1D—C1D—C6D—O1D | −32.3 (3) |
C2B—C1B—C6B—O1B | 88.3 (2) | C2D—C1D—C6D—O1D | 87.0 (3) |
N1B—C1B—C6B—N2B | 151.1 (2) | N1D—C1D—C6D—N2D | 150.2 (2) |
C2B—C1B—C6B—N2B | −90.2 (2) | C2D—C1D—C6D—N2D | −90.5 (2) |
C6B—N2B—C7B—C8B | 149.5 (2) | C6D—N2D—C7D—C11D | −84.8 (3) |
C6B—N2B—C7B—C11B | −85.2 (2) | C6D—N2D—C7D—C8D | 151.4 (2) |
N2B—C7B—C8B—C9B | −66.8 (3) | N2D—C7D—C8D—C9D | −67.3 (3) |
C11B—C7B—C8B—C9B | 168.9 (2) | C11D—C7D—C8D—C9D | 169.9 (2) |
N2B—C7B—C8B—C10B | 169.4 (2) | N2D—C7D—C8D—C10D | 170.8 (2) |
C11B—C7B—C8B—C10B | 45.2 (3) | C11D—C7D—C8D—C10D | 47.9 (3) |
N2B—C7B—C11B—O3B | 125.4 (2) | N2D—C7D—C11D—O3D | 126.7 (2) |
C8B—C7B—C11B—O3B | −110.0 (2) | C8D—C7D—C11D—O3D | −110.3 (2) |
N2B—C7B—C11B—O2B | −56.1 (3) | N2D—C7D—C11D—O2D | −55.2 (3) |
C8B—C7B—C11B—O2B | 68.5 (3) | C8D—C7D—C11D—O2D | 67.8 (3) |
(lv2p)
L-leucyl-
L-valine 2-propanol (1:1)
top
Crystal data top
C14H30N2O4 | F(000) = 640 |
Mr = 290.40 | Dx = 1.138 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.1709 (1) Å | Cell parameters from 7127 reflections |
b = 14.6136 (2) Å | µ = 0.08 mm−1 |
c = 22.4230 (4) Å | T = 150 K |
V = 1694.40 (5) Å3 | Block, colourless |
Z = 4 | 0.55 × 0.25 × 0.10 mm |
Data collection top
Siemens SMART CCD diffractometer | 12521 independent reflections |
Radiation source: fine-focus sealed tube | 9601 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Sets of exposures each taken over 0.6° ω rotation scans | θmax = 43.2°, θmin = 2.3° |
Absorption correction: multiscan (SADABS; sheldrick, 1996) ? | h = −9→7 |
Tmin = 0.952, Tmax = 0.980 | k = −28→28 |
32534 measured reflections | l = −43→36 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Calculated w = 1/[σ2(Fo2) + (0.0524P)2 + 0.1584P] where P = (Fo2 + 2Fc2)/3 |
12521 reflections | (Δ/σ)max = 0.007 |
230 parameters | Δρmax = 0.34 e Å−3 |
3 restraints | Δρmin = −0.23 e Å−3 |
Crystal data top
C14H30N2O4 | V = 1694.40 (5) Å3 |
Mr = 290.40 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.1709 (1) Å | µ = 0.08 mm−1 |
b = 14.6136 (2) Å | T = 150 K |
c = 22.4230 (4) Å | 0.55 × 0.25 × 0.10 mm |
Data collection top
Siemens SMART CCD diffractometer | 12521 independent reflections |
Absorption correction: multiscan (SADABS; sheldrick, 1996) ? | 9601 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 0.980 | Rint = 0.034 |
32534 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.056 | 3 restraints |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.34 e Å−3 |
12521 reflections | Δρmin = −0.23 e Å−3 |
230 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement on F2 for ALL reflections. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 0.4131 (2) | 0.46498 (4) | 0.20213 (4) | 0.0324 (2) | |
O2A | 0.4223 (5) | 0.8049 (3) | 0.2105 (3) | 0.0306 (6) | 0.50 |
O2B | 0.4895 (5) | 0.8032 (3) | 0.2117 (2) | 0.0272 (5) | 0.50 |
O3A | 0.7834 (4) | 0.72478 (11) | 0.22477 (10) | 0.0270 (3) | 0.50 |
O3B | 0.7750 (4) | 0.69564 (12) | 0.23718 (9) | 0.0274 (3) | 0.50 |
N1A | 0.0110 (6) | 0.38369 (12) | 0.2450 (2) | 0.0207 (5) | 0.50 |
H1A | −0.122 (3) | 0.3575 (5) | 0.2660 (8) | 0.031* | 0.50 |
H2A | 0.163 (3) | 0.3553 (5) | 0.2545 (8) | 0.031* | 0.50 |
H3A | −0.020 (4) | 0.37752 (15) | 0.2050 (6) | 0.031* | 0.50 |
N1B | −0.0467 (6) | 0.38817 (13) | 0.2423 (2) | 0.0185 (5) | 0.50 |
H1B | −0.192 (3) | 0.3715 (5) | 0.2620 (7) | 0.028* | 0.50 |
H2B | 0.083 (2) | 0.3490 (6) | 0.2513 (8) | 0.028* | 0.50 |
H3B | −0.077 (4) | 0.3868 (3) | 0.2026 (6) | 0.028* | 0.50 |
N2A | 0.23957 (12) | 0.60838 (4) | 0.20816 (3) | 0.01726 (10) | |
H4A | 0.109 (3) | 0.6381 (9) | 0.2167 (6) | 0.021* | |
C1A | 0.02897 (15) | 0.48323 (4) | 0.26047 (3) | 0.01735 (11) | |
H11A | −0.13819 (15) | 0.51571 (4) | 0.25306 (3) | 0.021* | |
C2A | 0.1100 (2) | 0.48923 (6) | 0.32621 (3) | 0.02267 (13) | |
H21A | 0.1946 (2) | 0.54909 (6) | 0.33308 (3) | 0.027* | |
H22A | 0.2395 (2) | 0.44092 (6) | 0.33432 (3) | 0.027* | |
C3A | −0.1152 (2) | 0.47873 (6) | 0.37079 (4) | 0.02484 (14) | |
H31A | −0.2327 (2) | 0.42915 (6) | 0.35627 (4) | 0.030* | |
C4A | −0.2691 (2) | 0.56778 (8) | 0.37477 (5) | 0.0327 (2) | |
H41A | −0.3336 (18) | 0.5842 (4) | 0.33510 (10) | 0.049 (3)* | |
H42A | −0.1569 (6) | 0.6167 (2) | 0.3898 (5) | 0.049 (3)* | |
H43A | −0.4154 (12) | 0.5595 (2) | 0.4020 (4) | 0.049 (3)* | |
C5A | −0.0140 (3) | 0.45234 (10) | 0.43247 (5) | 0.0457 (3) | |
H51A | 0.065 (2) | 0.3915 (4) | 0.43060 (12) | 0.053 (3)* | |
H52A | −0.1578 (5) | 0.4515 (7) | 0.46095 (12) | 0.053 (3)* | |
H53A | 0.1153 (16) | 0.4971 (5) | 0.4454 (2) | 0.053 (3)* | |
C6A | 0.24422 (15) | 0.51885 (5) | 0.21990 (3) | 0.01800 (11) | |
C7A | 0.43577 (14) | 0.65232 (5) | 0.17033 (3) | 0.01706 (11) | |
H71A | 0.57409 (14) | 0.60681 (5) | 0.16076 (3) | 0.020* | |
C8A | 0.3138 (2) | 0.68647 (6) | 0.11192 (4) | 0.02339 (14) | |
H81A | 0.1695 (2) | 0.72942 (6) | 0.12186 (4) | 0.028* | |
C9A | 0.2032 (2) | 0.60580 (8) | 0.07652 (4) | 0.0361 (2) | |
H91A | 0.1272 (19) | 0.62829 (12) | 0.0393 (2) | 0.050 (3)* | |
H92A | 0.0696 (15) | 0.5752 (5) | 0.1002 (2) | 0.050 (3)* | |
H93A | 0.3420 (5) | 0.5623 (4) | 0.0674 (4) | 0.050 (3)* | |
C10A | 0.5134 (2) | 0.73759 (8) | 0.07444 (5) | 0.0365 (2) | |
H04A | 0.4351 (7) | 0.7561 (7) | 0.0365 (2) | 0.062 (3)* | |
H05A | 0.6615 (11) | 0.6975 (3) | 0.0667 (5) | 0.062 (3)* | |
H06A | 0.5718 (18) | 0.7921 (5) | 0.0961 (2) | 0.062 (3)* | |
C11A | 0.5580 (3) | 0.73442 (9) | 0.20341 (7) | 0.0168 (2)* | 0.50 |
C11B | 0.5772 (3) | 0.72276 (9) | 0.21090 (7) | 0.0168 (2)* | 0.50 |
O1C | 0.79845 (15) | 0.42531 (5) | 0.12635 (3) | 0.03048 (14) | |
H1C | 0.658 (4) | 0.4386 (12) | 0.1460 (8) | 0.046* | |
C1C | 0.6655 (3) | 0.26692 (8) | 0.11978 (7) | 0.0483 (3) | |
H11C | 0.5156 (15) | 0.2794 (2) | 0.1452 (4) | 0.059 (3)* | |
H12C | 0.8120 (9) | 0.2480 (5) | 0.1446 (4) | 0.059 (3)* | |
H13C | 0.623 (2) | 0.2179 (3) | 0.09162 (7) | 0.059 (3)* | |
C2C | 0.7370 (2) | 0.35291 (7) | 0.08548 (4) | 0.0307 (2) | |
H21C | 0.5866 (2) | 0.37198 (7) | 0.06036 (4) | 0.037* | |
C3C | 0.9697 (3) | 0.33978 (13) | 0.04605 (7) | 0.0551 (4) | |
H31C | 1.0064 (17) | 0.3968 (3) | 0.0247 (5) | 0.081 (4)* | |
H32C | 0.9348 (11) | 0.2909 (7) | 0.0172 (4) | 0.081 (4)* | |
H33C | 1.1193 (7) | 0.3231 (10) | 0.07057 (10) | 0.081 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0348 (3) | 0.0226 (2) | 0.0399 (4) | 0.0137 (2) | 0.0183 (3) | 0.0097 (2) |
O2A | 0.0251 (12) | 0.0195 (6) | 0.0472 (11) | 0.0065 (10) | 0.0025 (13) | −0.0104 (6) |
O2B | 0.0286 (12) | 0.0147 (6) | 0.0384 (9) | 0.0032 (10) | 0.0045 (13) | −0.0047 (5) |
O3A | 0.0177 (6) | 0.0227 (6) | 0.0406 (10) | 0.0019 (6) | −0.0056 (6) | −0.0083 (6) |
O3B | 0.0182 (6) | 0.0278 (7) | 0.0362 (8) | 0.0042 (7) | −0.0037 (6) | −0.0065 (7) |
N1A | 0.0256 (14) | 0.0118 (6) | 0.0247 (9) | 0.0015 (6) | 0.0057 (12) | 0.0019 (6) |
N1B | 0.0210 (11) | 0.0136 (6) | 0.0207 (7) | 0.0041 (5) | 0.0031 (10) | 0.0003 (5) |
N2A | 0.0153 (2) | 0.0141 (2) | 0.0224 (2) | 0.0008 (2) | 0.0041 (2) | 0.0003 (2) |
C1A | 0.0194 (3) | 0.0141 (2) | 0.0186 (2) | 0.0003 (2) | 0.0020 (2) | 0.0011 (2) |
C2A | 0.0200 (3) | 0.0289 (3) | 0.0191 (3) | 0.0030 (3) | 0.0011 (2) | 0.0008 (3) |
C3A | 0.0287 (4) | 0.0263 (3) | 0.0195 (3) | −0.0031 (3) | 0.0044 (3) | −0.0013 (3) |
C4A | 0.0269 (4) | 0.0377 (4) | 0.0336 (4) | 0.0053 (4) | 0.0064 (4) | −0.0041 (4) |
C5A | 0.0552 (7) | 0.0605 (7) | 0.0215 (4) | 0.0168 (6) | 0.0063 (4) | 0.0081 (4) |
C6A | 0.0185 (3) | 0.0159 (2) | 0.0196 (2) | 0.0028 (2) | 0.0028 (2) | 0.0021 (2) |
C7A | 0.0158 (3) | 0.0147 (2) | 0.0207 (3) | −0.0002 (2) | 0.0033 (2) | −0.0005 (2) |
C8A | 0.0224 (3) | 0.0251 (3) | 0.0227 (3) | −0.0021 (3) | 0.0009 (3) | 0.0048 (3) |
C9A | 0.0432 (6) | 0.0418 (5) | 0.0234 (4) | −0.0135 (5) | −0.0050 (4) | 0.0008 (4) |
C10A | 0.0399 (5) | 0.0398 (5) | 0.0299 (4) | −0.0109 (4) | 0.0058 (4) | 0.0106 (4) |
O1C | 0.0278 (3) | 0.0271 (3) | 0.0365 (3) | −0.0018 (2) | 0.0105 (3) | −0.0036 (3) |
C1C | 0.0631 (9) | 0.0321 (5) | 0.0498 (7) | −0.0130 (5) | 0.0020 (6) | −0.0065 (5) |
C2C | 0.0234 (4) | 0.0393 (4) | 0.0294 (4) | −0.0023 (3) | 0.0008 (3) | −0.0047 (3) |
C3C | 0.0437 (7) | 0.0791 (10) | 0.0426 (6) | −0.0062 (7) | 0.0163 (6) | −0.0240 (7) |
Geometric parameters (Å, º) top
O1A—C6A | 1.2414 (9) | C5A—H51A | 0.98 |
O2A—C11A | 1.256 (4) | C5A—H52A | 0.98 |
O2B—C11B | 1.260 (4) | C5A—H53A | 0.98 |
O3A—C11A | 1.268 (3) | C7A—C8A | 1.5370 (11) |
O3B—C11B | 1.245 (3) | C7A—C11A | 1.5457 (13) |
N1A—C1A | 1.4984 (14) | C7A—C11B | 1.5563 (13) |
N1A—H1A | 0.915 (13) | C7A—H71A | 1.00 |
N1A—H2A | 0.915 (13) | C8A—C10A | 1.5264 (13) |
N1A—H3A | 0.915 (13) | C8A—C9A | 1.5319 (14) |
N1B—C1A | 1.4999 (14) | C8A—H81A | 1.00 |
N1B—H1B | 0.903 (13) | C9A—H91A | 0.98 |
N1B—H2B | 0.903 (13) | C9A—H92A | 0.98 |
N1B—H3B | 0.903 (13) | C9A—H93A | 0.98 |
N2A—C6A | 1.3348 (9) | C10A—H04A | 0.98 |
N2A—C7A | 1.4701 (9) | C10A—H05A | 0.98 |
N2A—H4A | 0.827 (14) | C10A—H06A | 0.98 |
C1A—C6A | 1.5289 (10) | O1C—C2C | 1.4354 (12) |
C1A—C2A | 1.5349 (11) | O1C—H1C | 0.87 (2) |
C1A—H11A | 1.00 | C1C—C2C | 1.519 (2) |
C2A—C3A | 1.5425 (12) | C1C—H11C | 0.98 |
C2A—H21A | 0.99 | C1C—H12C | 0.98 |
C2A—H22A | 0.99 | C1C—H13C | 0.98 |
C3A—C4A | 1.5279 (14) | C2C—C3C | 1.505 (2) |
C3A—C5A | 1.5281 (14) | C2C—H21C | 1.00 |
C3A—H31A | 1.00 | C3C—H31C | 0.98 |
C4A—H41A | 0.98 | C3C—H32C | 0.98 |
C4A—H42A | 0.98 | C3C—H33C | 0.98 |
C4A—H43A | 0.98 | | |
| | | |
C1A—N1A—H1A | 109.5 (2) | N2A—C7A—C11A | 110.14 (8) |
C1A—N1A—H2A | 109.47 (12) | C8A—C7A—C11A | 108.95 (8) |
H1A—N1A—H2A | 109.5 | N2A—C7A—C11B | 106.01 (8) |
C1A—N1A—H3A | 109.5 (2) | C8A—C7A—C11B | 118.44 (8) |
H1A—N1A—H3A | 109.5 | N2A—C7A—H71A | 109.07 (3) |
H2A—N1A—H3A | 109.5 | C8A—C7A—H71A | 109.07 (4) |
C1A—N1B—H1B | 109.5 (2) | C11A—C7A—H71A | 109.07 (7) |
C1A—N1B—H2B | 109.47 (12) | C10A—C8A—C9A | 110.11 (8) |
H1B—N1B—H2B | 109.5 | C10A—C8A—C7A | 110.52 (7) |
C1A—N1B—H3B | 109.5 (2) | C9A—C8A—C7A | 110.17 (7) |
H1B—N1B—H3B | 109.5 | C10A—C8A—H81A | 108.66 (6) |
H2B—N1B—H3B | 109.5 | C9A—C8A—H81A | 108.66 (6) |
C6A—N2A—C7A | 121.98 (6) | C7A—C8A—H81A | 108.66 (4) |
C6A—N2A—H4A | 119.0 (9) | C8A—C9A—H91A | 109.47 (5) |
C7A—N2A—H4A | 118.0 (9) | C8A—C9A—H92A | 109.47 (5) |
N1A—C1A—C6A | 103.8 (2) | H91A—C9A—H92A | 109.5 |
N1B—C1A—C6A | 110.1 (2) | C8A—C9A—H93A | 109.47 (6) |
N1A—C1A—C2A | 107.1 (2) | H91A—C9A—H93A | 109.5 |
N1B—C1A—C2A | 112.7 (2) | H92A—C9A—H93A | 109.5 |
C6A—C1A—C2A | 110.68 (6) | C8A—C10A—H04A | 109.47 (6) |
N1A—C1A—H11A | 111.63 (12) | C8A—C10A—H05A | 109.47 (6) |
C6A—C1A—H11A | 111.63 (4) | H04A—C10A—H05A | 109.5 |
C2A—C1A—H11A | 111.63 (4) | C8A—C10A—H06A | 109.47 (6) |
C1A—C2A—C3A | 114.24 (7) | H04A—C10A—H06A | 109.5 |
C1A—C2A—H21A | 108.70 (4) | H05A—C10A—H06A | 109.5 |
C3A—C2A—H21A | 108.70 (5) | O2A—C11A—O3A | 123.8 (2) |
C1A—C2A—H22A | 108.70 (4) | O2A—C11A—C7A | 118.0 (2) |
C3A—C2A—H22A | 108.70 (5) | O3A—C11A—C7A | 118.09 (13) |
H21A—C2A—H22A | 107.6 | O3B—C11B—O2B | 125.8 (2) |
C4A—C3A—C5A | 109.89 (8) | O3B—C11B—C7A | 116.88 (14) |
C4A—C3A—C2A | 110.26 (8) | O2B—C11B—C7A | 117.2 (2) |
C5A—C3A—C2A | 110.69 (9) | C2C—O1C—H1C | 107.6 (11) |
C4A—C3A—H31A | 108.65 (6) | C2C—C1C—H11C | 109.47 (7) |
C5A—C3A—H31A | 108.65 (7) | C2C—C1C—H12C | 109.47 (8) |
C2A—C3A—H31A | 108.65 (5) | H11C—C1C—H12C | 109.5 |
C3A—C4A—H41A | 109.47 (5) | C2C—C1C—H13C | 109.47 (6) |
C3A—C4A—H42A | 109.47 (6) | H11C—C1C—H13C | 109.5 |
H41A—C4A—H42A | 109.5 | H12C—C1C—H13C | 109.5 |
C3A—C4A—H43A | 109.47 (5) | O1C—C2C—C3C | 106.98 (9) |
H41A—C4A—H43A | 109.5 | O1C—C2C—C1C | 109.91 (9) |
H42A—C4A—H43A | 109.5 | C3C—C2C—C1C | 112.74 (12) |
C3A—C5A—H51A | 109.47 (6) | O1C—C2C—H21C | 109.05 (5) |
C3A—C5A—H52A | 109.47 (6) | C3C—C2C—H21C | 109.05 (8) |
H51A—C5A—H52A | 109.5 | C1C—C2C—H21C | 109.05 (8) |
C3A—C5A—H53A | 109.47 (7) | C2C—C3C—H31C | 109.47 (9) |
H51A—C5A—H53A | 109.5 | C2C—C3C—H32C | 109.47 (7) |
H52A—C5A—H53A | 109.5 | H31C—C3C—H32C | 109.5 |
O1A—C6A—N2A | 124.82 (7) | C2C—C3C—H33C | 109.47 (8) |
O1A—C6A—C1A | 119.15 (6) | H31C—C3C—H33C | 109.5 |
N2A—C6A—C1A | 115.98 (6) | H32C—C3C—H33C | 109.5 |
N2A—C7A—C8A | 110.50 (6) | | |
| | | |
N1A—C1A—C2A—C3A | −82.5 (2) | C11A—C7A—C8A—C10A | 55.17 (11) |
N1B—C1A—C2A—C3A | −71.2 (2) | C11B—C7A—C8A—C10A | 53.79 (12) |
C6A—C1A—C2A—C3A | 165.05 (7) | N2A—C7A—C8A—C9A | −61.79 (9) |
C1A—C2A—C3A—C4A | −77.88 (9) | C11A—C7A—C8A—C9A | 177.07 (10) |
C1A—C2A—C3A—C5A | 160.31 (9) | C11B—C7A—C8A—C9A | 175.70 (10) |
C7A—N2A—C6A—O1A | 2.03 (13) | N2A—C7A—C11A—O2A | −71.5 (3) |
C7A—N2A—C6A—C1A | 179.37 (6) | C8A—C7A—C11A—O2A | 49.8 (3) |
N1A—C1A—C6A—O1A | −26.0 (2) | C11B—C7A—C11A—O2A | −137.5 (9) |
N1B—C1A—C6A—O1A | −36.6 (2) | N2A—C7A—C11A—O3A | 104.4 (2) |
C2A—C1A—C6A—O1A | 88.61 (9) | C8A—C7A—C11A—O3A | −134.3 (2) |
N1A—C1A—C6A—N2A | 156.5 (2) | C11B—C7A—C11A—O3A | 38.4 (7) |
N1B—C1A—C6A—N2A | 145.9 (2) | N2A—C7A—C11B—O3B | 92.0 (2) |
C2A—C1A—C6A—N2A | −88.89 (8) | C8A—C7A—C11B—O3B | −143.2 (2) |
C6A—N2A—C7A—C8A | 112.83 (8) | C11A—C7A—C11B—O3B | −151.1 (9) |
C6A—N2A—C7A—C11A | −126.74 (9) | N2A—C7A—C11B—O2B | −91.6 (3) |
C6A—N2A—C7A—C11B | −117.65 (9) | C8A—C7A—C11B—O2B | 33.1 (3) |
N2A—C7A—C8A—C10A | 176.30 (7) | C11A—C7A—C11B—O2B | 25.2 (7) |
Experimental details
| (lvm) | (lve) | (lv2p) |
Crystal data |
Chemical formula | C12H26N2O4 | C13H28N2O4 | C14H30N2O4 |
Mr | 262.35 | 276.37 | 290.40 |
Crystal system, space group | Monoclinic, P21 | Monoclinic, P21 | Orthorhombic, P212121 |
Temperature (K) | 150 | 150 | 150 |
a, b, c (Å) | 5.2890 (1), 12.6877 (1), 11.4872 (1) | 11.0112 (1), 23.5186 (1), 12.2636 (1) | 5.1709 (1), 14.6136 (2), 22.4230 (4) |
α, β, γ (°) | 90, 95.8136 (5), 90 | 90, 90.0121 (8), 90 | 90, 90, 90 |
V (Å3) | 766.87 (1) | 3175.88 (4) | 1694.40 (5) |
Z | 2 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.09 | 0.08 |
Crystal size (mm) | 0.50 × 0.40 × 0.35 | 0.60 × 0.50 × 0.25 | 0.55 × 0.25 × 0.10 |
|
Data collection |
Diffractometer | Siemens SMART CCD diffractometer | Siemens SMART CCD diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Multiscan (SADABS; Sheldrick, 1996) | Multiscan (SADABS; Sheldrick, 1996) | Multiscan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.959, 0.971 | 0.950, 0.979 | 0.952, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17325, 12154, 8119 | 50343, 38561, 28178 | 32534, 12521, 9601 |
Rint | 0.049 | 0.039 | 0.034 |
(sin θ/λ)max (Å−1) | 1.074 | 0.962 | 0.962 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.179, 0.99 | 0.065, 0.144, 1.07 | 0.056, 0.136, 1.11 |
No. of reflections | 12153 | 38561 | 12521 |
No. of parameters | 203 | 734 | 230 |
No. of restraints | 1 | 1 | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.64, −0.28 | 0.54, −0.32 | 0.34, −0.23 |
Absolute structure | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | ? |
Absolute structure parameter | ? | −0.24 (45) | ? |
Table 3. Selected bond lengths (Å) bond angles (°) and
torsion angles (°) for L-Leu-L-Val alcohol solvates top | LVM | | LVE | | | | LV2P |
| A | A | B | C | D | A | B |
N1-C1 | 1.4863 (11) | 1.488 (2) | 1.492 (2) | 1.493 (2) | 1.499 (2) | 1.4984 (14) | 1.4999 (14) |
N2-C6 | 1.3316 (11) | 1.331 (3) | 1.340 (3) | 1.332 (3) | 1.342 (3) | 1.3348 (9) | – |
O1-C6 | 1.2394 (11) | 1.240 (2) | 1.233 (2) | 1.233 (2) | 1.228 (2) | 1.2414 (9) | – |
O2-C11 | 1.2495 (11) | 1.248 (2) | 1.261 (2) | 1.241 (3) | 1.257 (3) | 1.256 (4) | 1.260 (3) |
O3-C11 | 1.2599 (11) | 1.263 (2) | 1.247 (2) | 1.269 (2) | 1.247 (2) | 1.268 (3) | 1.245 (3) |
C7-C11 | 1.5454 (12) | 1.547 (3) | 1.539 (3) | 1.544 (3) | 1.537 (3) | 1.5457 (13) | 1.5563 (13) |
C3-C4 | 1.532 (2) | 1.511 (5) | 1.523 (4) | 1.521 (4) | 1.534 (4) | 1.5279 (14) | – |
O1-C* | 1.384 (2) | 1.424 (4) | 1.446 (4) | 1.389 (4) | 1.409 (3) | 1.4354 (12) | – |
N1-C1-C6 | 108.01 (7) | 108.42 (15) | 108.08 (15) | 107.63 (15) | 108.0 (2) | 103.8 (2) | 110.1 (2) |
C1-C6-N2 | 114.36 (7) | 115.3 (2) | 114.7 (2) | 114.5 (2) | 114.6 (2) | 115.98 (6) | – |
C6-N2-C7 | 124.17 (7) | 124.3 (2) | 122.1 (2) | 123.6 (2) | 121.3 (2) | 121.98 (6) | – |
N2-C7-C11 | 107.16 (7) | 107.7 (2) | 110.5 (2) | 107.5 (2) | 110.1 (2) | 110.14 (8) | 106.01 (8) |
O2-C11-O3 | 125.37 (9) | 125.2 (2) | 124.0 (2) | 125.3 (2) | 124.5 (2) | 123.8 (2) | 125.8 (2) |
C2-C3-C5 | 108.59 (15) | 109.6 (3) | 109.1 (2) | 109.8 (2) | 110.4 (2) | 110.69 (9) | – |
C9-C8-C10 | 110.99 (12) | 111.4 (3) | 110.9 (3) | 110.4 (3) | 110.3 (3) | 110.11 (8) | – |
O1-C-C* | – | 112.2 (3) | 112.5 (3) | 112.9 (4) | 112.3 (2) | 109.91 (9) | – |
N1-C1-C6-N2 (y1) | 153.02 (8) | 151.0 (2) | 151.1 (2) | 151.5 (2) | 150.2 (2) | 156.5 (2) | 145.9 (2) |
C1-C6-N2-C7 (w1) | 169.87 (8) | 162.9 (2) | 168.1 (2) | 162.3 (2) | 168.4 (2) | 179.37 (6) | – |
C6-N2-C7-C11 (j2) | -116.54 (9) | -87.6 (3) | -85.2 (2) | -88.4 (3) | -84.8 (3) | -126.74 (9) | -117.65 (9) |
N2-C7-C11-O2 (yT) | -64.79 (10) | -54.8 (3) | -56.1 (2) | -54.2 (2) | -55.2 (3) | -71.5 (3) | -91.6 (3) |
N1-C1-C2-C3 (c11) | -73.34 (11) | -73.5 (3) | -76.9 (2) | -72.5 (2) | -75.3 (2) | -82.5 (2) | -71.2 (2) |
C1-C2-C3-C4 (c12,1) | -78.59 (13) | -72.6 (3) | -77.4 (3) | -71.6 (3) | -78.7 (3) | -77.88 (9) | – |
C1-C2-C3-C5 (c12,2) | 160.12 (13) | 164.2 (3) | 160.0 (2) | 166.5 (2) | 159.3 (2) | 160.31 (9) | – |
N2-C7-C8-C9 (c21,1) | -62.30 (11) | -64.1 (3) | -66.8 (3) | -65.8 (3) | -67.3 (3) | -61.79 (9) | – |
N2-C7-C8-C10 (c22,2) | 174.33 (11) | 170.7 (2) | 169.4 (2) | 171.5 (2) | 170.8 (2) | 176.30 (7) | – |
In solvent molecule. For LVE these are E, F, G and H. For LV2P
the O1B-C2B-C1B angle is given. |