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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

cif

Crystallographic Information File (CIF)
Contains datablocks lvm, lve, lv2p, global

hkl

Structure factor file (CIF format)
Contains datablock lvtest

hkl

Structure factor file (CIF format)
Contains datablock lvm2

hkl

Structure factor file (CIF format)
Contains datablock lv2ptest

CCDC references: 131750; 131751; 131752

Computing details top

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).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(lvm) L-leucyl-L-valine methanol (1:1) top
Crystal data top
C12H26N2O4F(000) = 288
Mr = 262.35Dx = 1.136 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 5.2890 (1) ÅCell parameters from 8192 reflections
b = 12.6877 (1) ŵ = 0.08 mm1
c = 11.4872 (1) ÅT = 150 K
β = 95.8136 (5)°Block, colourless
V = 766.87 (1) Å30.50 × 0.40 × 0.35 mm
Z = 2
Data collection top
Siemens SMART CCD
diffractometer
12154 independent reflections
Radiation source: fine-focus sealed tube8119 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Sets of exposures each taken over 0.6° ω rotation scansθmax = 49.8°, θmin = 1.8°
Absorption correction: multiscan (SADABS; sheldrick, 1996)
?
h = 118
Tmin = 0.959, Tmax = 0.971k = 2724
17325 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H atoms treated by a mixture of independent and constrained refinement
S = 0.99Calculated w = 1/[σ2(Fo2) + (0.0864P)2]
where P = (Fo2 + 2Fc2)/3
12153 reflections(Δ/σ)max = 0.083
203 parametersΔρmax = 0.64 e Å3
1 restraintΔρmin = 0.28 e Å3
Crystal data top
C12H26N2O4V = 766.87 (1) Å3
Mr = 262.35Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.2890 (1) ŵ = 0.08 mm1
b = 12.6877 (1) ÅT = 150 K
c = 11.4872 (1) Å0.50 × 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 = 0.971Rint = 0.049
17325 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0661 restraint
wR(F2) = 0.179H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.64 e Å3
12153 reflectionsΔρmin = 0.28 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1A0.5902 (2)0.13448 (7)0.38070 (9)0.0296 (2)
O2A0.53664 (15)0.24568 (6)0.36754 (9)0.0269 (2)
O3A0.18301 (14)0.15513 (7)0.38891 (9)0.0280 (2)
N1A1.04959 (15)0.19362 (6)0.48622 (8)0.01919 (13)
H1A1.189 (4)0.210 (2)0.529 (2)0.046 (3)*
H2A0.924 (5)0.229 (2)0.522 (2)0.046 (3)*
H3A1.048 (5)0.213 (2)0.409 (2)0.046 (3)*
N2A0.72874 (13)0.03377 (6)0.35468 (7)0.01776 (12)
H4A0.844 (3)0.0758 (15)0.3650 (15)0.021*
C1A0.9823 (2)0.07992 (7)0.48747 (8)0.01674 (13)
H11A1.118 (3)0.0394 (8)0.4660 (4)0.020*
C2A0.9180 (2)0.04720 (9)0.60998 (9)0.0228 (2)
H21A0.8320 (13)0.0211 (10)0.60412 (12)0.027*
H22A0.7991 (17)0.0985 (7)0.6371 (4)0.027*
C3A1.1505 (3)0.03900 (11)0.70202 (11)0.0344 (3)
H31A1.268 (3)0.1002 (14)0.6916 (3)0.041*
C4A1.2954 (3)0.0642 (2)0.6887 (2)0.0461 (4)
H41A1.443 (3)0.0661 (7)0.7454 (15)0.074 (5)*
H42A1.348 (3)0.0683 (7)0.6108 (16)0.074 (5)*
H43A1.186 (2)0.1231 (11)0.7016 (17)0.074 (5)*
C5A1.0579 (6)0.0453 (2)0.82487 (15)0.0688 (8)
H51A1.211 (3)0.043 (2)0.8868 (12)0.098 (7)*
H52A0.942 (5)0.0172 (16)0.8367 (9)0.098 (7)*
H53A0.960 (5)0.1139 (17)0.8325 (8)0.098 (7)*
C6A0.7484 (2)0.06290 (7)0.39980 (8)0.01746 (13)
C7A0.50317 (15)0.07368 (7)0.28394 (8)0.01662 (12)
H71A0.385 (2)0.0219 (10)0.2752 (2)0.020*
C8A0.5706 (2)0.10789 (10)0.16254 (9)0.0244 (2)
H81A0.704 (3)0.1588 (10)0.1731 (2)0.029*
C9A0.6661 (3)0.01418 (14)0.09599 (12)0.0390 (3)
H91A0.809 (3)0.0182 (9)0.1423 (9)0.052 (4)*
H92A0.530 (2)0.0370 (9)0.0812 (12)0.052 (4)*
H93A0.720 (3)0.0382 (4)0.0222 (12)0.052 (4)*
C10A0.3425 (3)0.1595 (2)0.09337 (12)0.0416 (3)
H04A0.303 (2)0.2254 (14)0.1308 (11)0.066 (5)*
H05A0.3820 (15)0.1736 (14)0.0140 (15)0.066 (5)*
H06A0.197 (3)0.1126 (10)0.0912 (14)0.066 (5)*
C11A0.39812 (15)0.16608 (7)0.35230 (8)0.01668 (12)
O1B0.1617 (2)0.1901 (2)0.25127 (11)0.0375 (5)0.814 (6)
H1B0.292 (6)0.177 (3)0.269 (3)0.056*0.814 (6)
O10B0.2107 (11)0.2438 (6)0.2636 (5)0.0304 (14)*0.186 (6)
H1OB0.3329 (11)0.2045 (6)0.2876 (5)0.046*0.186 (6)
C1B0.1502 (4)0.2286 (2)0.13817 (15)0.0476 (4)
H11B0.1730 (4)0.1705 (2)0.08402 (15)0.141 (13)*0.814 (6)
H12B0.2852 (4)0.2809 (2)0.13298 (15)0.141 (13)*0.814 (6)
H13B0.0155 (4)0.2619 (2)0.11740 (15)0.141 (13)*0.814 (6)
H14B0.1687 (4)0.1540 (2)0.11895 (15)0.212*0.186 (6)
H15B0.2665 (4)0.2707 (2)0.09581 (15)0.212*0.186 (6)
H16B0.0251 (4)0.2511 (2)0.11534 (15)0.212*0.186 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0255 (3)0.0216 (3)0.0385 (4)0.0097 (3)0.0121 (3)0.0075 (3)
O2A0.0188 (3)0.0200 (3)0.0414 (4)0.0063 (2)0.0003 (3)0.0045 (3)
O3A0.0169 (3)0.0245 (3)0.0442 (5)0.0053 (2)0.0109 (3)0.0090 (3)
N1A0.0170 (3)0.0170 (3)0.0232 (3)0.0020 (2)0.0003 (2)0.0011 (2)
N2A0.0122 (2)0.0153 (3)0.0249 (3)0.0008 (2)0.0023 (2)0.0022 (2)
C1A0.0141 (3)0.0156 (3)0.0200 (3)0.0008 (2)0.0012 (2)0.0004 (2)
C2A0.0217 (3)0.0247 (4)0.0217 (4)0.0017 (3)0.0015 (3)0.0030 (3)
C3A0.0414 (6)0.0328 (5)0.0260 (5)0.0147 (5)0.0119 (4)0.0081 (4)
C4A0.0293 (6)0.0648 (11)0.0428 (7)0.0100 (6)0.0029 (5)0.0153 (7)
C5A0.121 (2)0.0606 (12)0.0222 (6)0.0259 (13)0.0058 (9)0.0002 (7)
C6A0.0135 (3)0.0169 (3)0.0212 (3)0.0015 (2)0.0015 (2)0.0015 (2)
C7A0.0120 (2)0.0167 (3)0.0206 (3)0.0000 (2)0.0008 (2)0.0010 (2)
C8A0.0198 (3)0.0331 (5)0.0204 (4)0.0015 (3)0.0022 (3)0.0040 (3)
C9A0.0388 (6)0.0511 (8)0.0284 (5)0.0057 (6)0.0093 (5)0.0070 (5)
C10A0.0339 (6)0.0623 (10)0.0273 (5)0.0131 (6)0.0028 (4)0.0152 (6)
C11A0.0126 (2)0.0156 (3)0.0214 (3)0.0007 (2)0.0007 (2)0.0001 (2)
O1B0.0223 (5)0.0625 (12)0.0274 (5)0.0139 (6)0.0007 (4)0.0112 (6)
C1B0.0570 (9)0.0516 (9)0.0334 (6)0.0141 (8)0.0002 (6)0.0091 (6)
Geometric parameters (Å, º) top
O1A—C6A1.2394 (11)C5A—H53A1.02 (2)
O2A—C11A1.2495 (11)C7A—C8A1.5366 (13)
O3A—C11A1.2599 (11)C7A—C11A1.5454 (12)
N1A—C1A1.4863 (11)C7A—H71A0.91 (2)
N1A—H1A0.87 (2)C8A—C10A1.524 (2)
N1A—H2A0.93 (2)C8A—C9A1.527 (2)
N1A—H3A0.92 (2)C8A—H81A0.96 (2)
N2A—C6A1.3316 (11)C9A—H91A0.970 (14)
N2A—C7A1.4641 (10)C9A—H92A0.970 (14)
N2A—H4A0.81 (2)C9A—H93A0.970 (14)
C1A—C6A1.5292 (11)C10A—H04A0.97 (2)
C1A—C2A1.5380 (13)C10A—H05A0.97 (2)
C1A—H11A0.94 (2)C10A—H06A0.97 (2)
C2A—C3A1.542 (2)O1B—C1B1.384 (2)
C2A—H21A0.978 (14)O1B—H1B0.72 (3)
C2A—H22A0.978 (14)O1B—H1OB0.975 (6)
C3A—C4A1.532 (2)O10B—C1B1.457 (6)
C3A—C5A1.542 (3)O10B—H1OB0.84
C3A—H31A1.01 (2)C1B—H11B0.98
C4A—H41A0.97 (2)C1B—H12B0.98
C4A—H42A0.97 (2)C1B—H13B0.98
C4A—H43A0.97 (2)C1B—H14B0.98
C5A—H51A1.02 (2)C1B—H15B0.98
C5A—H52A1.02 (2)C1B—H16B0.98
C1A—N1A—H1A114.7 (17)N2A—C7A—C11A107.16 (7)
C1A—N1A—H2A106.1 (16)C8A—C7A—C11A112.05 (8)
H1A—N1A—H2A104 (2)N2A—C7A—H71A109.02 (4)
C1A—N1A—H3A106.6 (17)C8A—C7A—H71A109.02 (5)
H1A—N1A—H3A114 (2)C11A—C7A—H71A109.02 (4)
H2A—N1A—H3A112 (2)C10A—C8A—C9A110.99 (12)
C6A—N2A—C7A124.17 (7)C10A—C8A—C7A110.50 (8)
C6A—N2A—H4A121.4 (13)C9A—C8A—C7A110.69 (10)
C7A—N2A—H4A114.4 (13)C10A—C8A—H81A108.18 (9)
N1A—C1A—C6A108.01 (7)C9A—C8A—H81A108.18 (7)
N1A—C1A—C2A110.26 (8)C7A—C8A—H81A108.18 (5)
C6A—C1A—C2A108.99 (7)C8A—C9A—H91A109.47 (7)
N1A—C1A—H11A109.85 (5)C8A—C9A—H92A109.47 (7)
C6A—C1A—H11A109.85 (4)H91A—C9A—H92A109.5
C2A—C1A—H11A109.85 (5)C8A—C9A—H93A109.47 (7)
C1A—C2A—C3A114.25 (9)H91A—C9A—H93A109.5
C1A—C2A—H21A108.69 (5)H92A—C9A—H93A109.5
C3A—C2A—H21A108.69 (6)C8A—C10A—H04A109.47 (9)
C1A—C2A—H22A108.69 (5)C8A—C10A—H05A109.47 (6)
C3A—C2A—H22A108.69 (7)H04A—C10A—H05A109.5
H21A—C2A—H22A107.6C8A—C10A—H06A109.47 (9)
C4A—C3A—C2A111.19 (11)H04A—C10A—H06A109.5
C4A—C3A—C5A110.11 (13)H05A—C10A—H06A109.5
C2A—C3A—C5A108.59 (15)O2A—C11A—O3A125.37 (9)
C4A—C3A—H31A108.97 (8)O2A—C11A—C7A116.65 (8)
C2A—C3A—H31A108.97 (6)O3A—C11A—C7A117.98 (8)
C5A—C3A—H31A108.97 (12)C1B—O1B—H1B107 (3)
C3A—C4A—H41A109.47 (8)C1B—O1B—H1OB106.6 (4)
C3A—C4A—H42A109.47 (8)C1B—O10B—H1B90 (2)
H41A—C4A—H42A109.5C1B—O10B—H1OB109.3 (2)
C3A—C4A—H43A109.47 (8)O1B—C1B—H11B109.47 (12)
H41A—C4A—H43A109.5O1B—C1B—H12B109.47 (12)
H42A—C4A—H43A109.5H11B—C1B—H12B109.5
C3A—C5A—H51A109.47 (12)O1B—C1B—H13B109.47 (9)
C3A—C5A—H52A109.47 (12)H11B—C1B—H13B109.5
H51A—C5A—H52A109.5H12B—C1B—H13B109.5
C3A—C5A—H53A109.47 (10)O10B—C1B—H14B109.5 (3)
H51A—C5A—H53A109.5O10B—C1B—H15B109.5 (3)
H52A—C5A—H53A109.5H14B—C1B—H15B109.5
O1A—C6A—N2A125.55 (8)O10B—C1B—H16B109.5 (2)
O1A—C6A—C1A119.98 (8)H14B—C1B—H16B109.5
N2A—C6A—C1A114.36 (7)H15B—C1B—H16B109.5
N2A—C7A—C8A110.51 (7)
N1A—C1A—C2A—C3A73.34 (11)C6A—N2A—C7A—C8A121.13 (10)
C6A—C1A—C2A—C3A168.26 (9)C6A—N2A—C7A—C11A116.54 (9)
C1A—C2A—C3A—C4A78.59 (13)N2A—C7A—C8A—C10A174.33 (11)
C1A—C2A—C3A—C5A160.12 (13)C11A—C7A—C8A—C10A54.91 (13)
C7A—N2A—C6A—O1A6.3 (2)N2A—C7A—C8A—C9A62.30 (11)
C7A—N2A—C6A—C1A169.87 (8)C11A—C7A—C8A—C9A178.28 (9)
N1A—C1A—C6A—O1A30.55 (12)N2A—C7A—C11A—O2A64.79 (10)
C2A—C1A—C6A—O1A89.25 (11)C8A—C7A—C11A—O2A56.58 (11)
N1A—C1A—C6A—N2A153.02 (8)N2A—C7A—C11A—O3A114.57 (9)
C2A—C1A—C6A—N2A87.18 (10)C8A—C7A—C11A—O3A124.06 (9)
(lve) L-leucyl-L-valine ethanol (1:1) top
Crystal data top
C13H28N2O4F(000) = 1216
Mr = 276.37Dx = 1.156 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.0112 (1) ÅCell parameters from 8192 reflections
b = 23.5186 (1) ŵ = 0.09 mm1
c = 12.2636 (1) ÅT = 150 K
β = 90.0121 (8)°Block, colourless
V = 3175.88 (4) Å30.60 × 0.50 × 0.25 mm
Z = 8
Data collection top
Siemens SMART CCD
diffractometer
38561 independent reflections
Radiation source: fine-focus sealed tube28178 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Sets of exposures each taken over 0.6° ω rotation scansθmax = 43.1°, θmin = 1.9°
Absorption correction: multiscan (SADABS; sheldrick, 1996)
?
h = 2120
Tmin = 0.950, Tmax = 0.979k = 4445
50343 measured reflectionsl = 2315
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144Calculated w = 1/[σ2(Fo2) + (0.0434P)2 + 0.3289P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.065
38561 reflectionsΔρmax = 0.54 e Å3
734 parametersΔρmin = 0.32 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.24 (45)
Crystal data top
C13H28N2O4V = 3175.88 (4) Å3
Mr = 276.37Z = 8
Monoclinic, P21Mo Kα radiation
a = 11.0112 (1) ŵ = 0.09 mm1
b = 23.5186 (1) ÅT = 150 K
c = 12.2636 (1) Å0.60 × 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 = 0.979Rint = 0.039
50343 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.065H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144Δρmax = 0.54 e Å3
S = 1.07Δρmin = 0.32 e Å3
38561 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
734 parametersAbsolute 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
xyzUiso*/Ueq
O1A0.09900 (14)0.94651 (7)0.14833 (14)0.0245 (3)
O2A0.06421 (14)0.95806 (8)0.20245 (14)0.0289 (3)
O3A0.24732 (11)0.93667 (7)0.13667 (12)0.0224 (3)
N1A0.09194 (14)0.99961 (7)0.24707 (12)0.0172 (2)
H1A0.1436 (14)1.0265 (6)0.2666 (4)0.024 (4)*
H2A0.0181 (13)1.0088 (7)0.2691 (4)0.024 (4)*
H3A0.1136 (15)0.9670 (6)0.2773 (5)0.024 (4)*
N2A0.0180 (2)0.92152 (9)0.0031 (2)0.0164 (3)
H4A0.076 (2)0.92140 (9)0.0162 (8)0.020*
C1A0.0927 (2)0.99360 (8)0.1263 (2)0.0143 (3)
H11A0.1744 (2)0.98034 (8)0.1012 (2)0.017*
C2A0.0622 (2)1.05117 (11)0.0738 (2)0.0179 (4)
H21A0.0106 (2)1.06696 (11)0.1102 (2)0.021*
H22A0.0411 (2)1.04470 (11)0.0037 (2)0.021*
C3A0.1641 (3)1.09540 (13)0.0793 (2)0.0250 (5)
H31A0.1968 (3)1.09577 (13)0.1554 (2)0.030*
C4A0.2676 (3)1.0818 (2)0.0027 (3)0.0456 (9)
H41A0.2969 (16)1.0432 (5)0.0169 (15)0.068*
H42A0.2391 (7)1.0845 (11)0.0729 (3)0.068*
H43A0.3339 (10)1.1090 (7)0.0143 (16)0.068*
C5A0.1122 (4)1.15480 (15)0.0544 (3)0.0398 (8)
H51A0.0432 (13)1.1624 (4)0.1027 (13)0.060*
H52A0.1752 (7)1.1836 (2)0.0662 (18)0.060*
H53A0.0851 (19)1.1562 (3)0.0217 (6)0.060*
C6A0.0043 (2)0.95045 (8)0.0942 (2)0.0154 (3)
C7A0.0732 (2)0.89021 (10)0.0578 (2)0.0161 (4)
H71A0.1362 (2)0.87557 (10)0.0062 (2)0.019*
C8A0.0137 (3)0.83991 (12)0.1171 (2)0.0210 (5)
H81A0.0554 (3)0.85534 (12)0.1609 (2)0.025*
C9A0.0386 (3)0.79698 (12)0.0367 (3)0.0346 (6)
H91A0.0967 (15)0.8161 (2)0.0115 (12)0.052*
H92A0.0273 (4)0.7806 (7)0.0069 (13)0.052*
H93A0.0800 (18)0.7666 (5)0.0769 (3)0.052*
C10A0.1018 (3)0.8117 (2)0.1964 (3)0.0295 (6)
H04A0.1349 (15)0.8405 (2)0.2461 (11)0.044*
H05A0.0588 (6)0.7826 (6)0.2386 (12)0.044*
H06A0.1683 (11)0.7940 (8)0.1556 (3)0.044*
C11A0.1331 (2)0.93193 (9)0.1391 (2)0.0162 (3)
O1B0.5474 (2)0.93906 (8)0.16286 (14)0.0312 (4)
O2B0.60970 (14)0.95462 (8)0.18257 (14)0.0265 (3)
O3B0.75266 (13)0.91765 (9)0.0772 (2)0.0404 (4)
N1B0.35106 (14)0.99688 (7)0.23991 (13)0.0179 (3)
H1B0.2876 (16)1.0172 (7)0.2539 (3)0.029 (4)*
H2B0.4140 (13)1.0122 (8)0.2698 (6)0.029 (4)*
H3B0.3410 (16)0.9630 (6)0.2656 (5)0.029 (4)*
N2B0.4549 (2)0.92255 (9)0.0001 (2)0.0154 (3)
H4B0.398 (2)0.9266 (2)0.0322 (12)0.019*
C1B0.3693 (2)0.99374 (8)0.1195 (2)0.0151 (3)
H1CB0.2914 (2)0.98328 (8)0.0827 (2)0.018*
C2B0.4137 (2)1.05192 (11)0.0782 (2)0.0175 (4)
H21B0.4773 (2)1.06625 (11)0.1282 (2)0.021*
H22B0.4510 (2)1.04697 (11)0.0054 (2)0.021*
C3B0.3118 (2)1.09652 (12)0.0701 (2)0.0213 (4)
H31B0.2591 (2)1.09317 (12)0.1362 (2)0.026*
C4B0.2333 (3)1.08738 (14)0.0306 (2)0.0274 (5)
H41B0.1633 (10)1.1131 (6)0.0281 (8)0.041*
H42B0.2049 (15)1.0479 (3)0.0324 (9)0.041*
H43B0.2813 (6)1.0953 (8)0.0962 (2)0.041*
C5B0.3688 (4)1.15653 (14)0.0687 (3)0.0354 (7)
H51B0.4187 (17)1.1618 (4)0.1341 (10)0.053*
H52B0.3042 (4)1.18518 (14)0.0674 (19)0.053*
H53B0.4198 (17)1.1607 (4)0.0037 (10)0.053*
C6B0.4658 (2)0.94861 (8)0.0965 (2)0.0162 (3)
C7B0.5503 (2)0.88668 (10)0.0444 (2)0.0142 (3)
H71B0.5927 (2)0.86820 (10)0.0184 (2)0.017*
C8B0.4974 (3)0.83940 (12)0.1157 (2)0.0198 (4)
H81B0.4410 (3)0.85731 (12)0.1696 (2)0.024*
C9B0.4241 (3)0.79782 (13)0.0469 (3)0.0316 (6)
H91B0.3934 (16)0.7671 (5)0.0934 (4)0.047*
H92B0.3557 (11)0.8178 (2)0.0132 (14)0.047*
H93B0.4761 (6)0.7818 (7)0.0102 (11)0.047*
C10B0.5969 (4)0.8084 (2)0.1794 (3)0.0314 (7)
H04B0.6407 (13)0.8357 (2)0.2253 (13)0.047*
H05B0.5601 (4)0.7790 (6)0.2254 (13)0.047*
H06B0.6537 (11)0.7906 (8)0.1281 (3)0.047*
C11B0.6446 (2)0.92283 (9)0.1059 (2)0.0169 (3)
O1E0.2411 (2)0.89284 (9)0.3009 (2)0.0331 (5)
H1E0.178 (3)0.9052 (17)0.271 (3)0.050*
C1E0.2673 (3)0.83947 (12)0.2513 (3)0.0421 (7)
H11E0.3366 (3)0.82159 (12)0.2897 (3)0.051*
H12E0.2916 (3)0.84578 (12)0.1746 (3)0.051*
C2E0.1608 (5)0.7999 (2)0.2544 (5)0.071 (2)
H21E0.1831 (11)0.7636 (5)0.221 (3)0.107*
H22E0.0928 (11)0.8169 (7)0.214 (2)0.107*
H23E0.137 (2)0.7934 (12)0.3303 (5)0.107*
O1F0.7564 (2)0.90558 (9)0.2837 (2)0.0265 (4)
H1F0.692 (3)0.9185 (15)0.272 (3)0.040*
C1F0.7733 (3)0.85523 (13)0.2178 (3)0.0345 (6)
H11F0.8548 (3)0.83914 (13)0.2326 (3)0.041*
H12F0.7701 (3)0.86593 (13)0.1398 (3)0.041*
C2F0.6784 (4)0.81042 (14)0.2399 (3)0.0434 (8)
H21F0.6971 (14)0.7762 (4)0.1976 (17)0.065*
H22F0.5983 (5)0.8249 (4)0.219 (2)0.065*
H23F0.6783 (17)0.8011 (8)0.3178 (5)0.065*
O1C0.65086 (13)0.05474 (7)0.64944 (13)0.0233 (3)
O2C0.68550 (14)0.04208 (8)0.29870 (15)0.0278 (3)
O3C0.50198 (11)0.06346 (7)0.36361 (12)0.0227 (3)
N1C0.84058 (14)0.00070 (7)0.74804 (12)0.0179 (3)
H1C0.8986 (18)0.0245 (8)0.7690 (5)0.045 (5)*
H2C0.7666 (16)0.0120 (9)0.7699 (5)0.045 (5)*
H3C0.8556 (19)0.0351 (7)0.7790 (7)0.045 (5)*
N2C0.7678 (2)0.07867 (9)0.5040 (2)0.0161 (3)
H4C0.843 (2)0.07862 (9)0.4787 (8)0.019*
C1C0.8421 (2)0.00651 (8)0.6268 (2)0.0147 (3)
H11C0.9238 (2)0.01953 (8)0.6016 (2)0.018*
C2C0.8095 (2)0.05070 (11)0.5736 (2)0.0187 (4)
H21C0.7905 (2)0.04394 (11)0.4957 (2)0.022*
H22C0.7351 (2)0.06562 (11)0.6087 (2)0.022*
C3C0.9096 (2)0.09655 (11)0.5808 (2)0.0221 (5)
H31C0.9400 (2)0.09821 (11)0.6575 (2)0.026*
C4C1.0152 (3)0.08204 (15)0.5059 (3)0.0455 (9)
H41C1.0468 (16)0.0443 (5)0.5246 (15)0.068*
H42C0.9873 (6)0.0820 (11)0.4300 (4)0.068*
H43C1.0796 (11)0.1104 (7)0.5148 (17)0.068*
C5C0.8574 (4)0.1540 (2)0.5509 (3)0.0416 (8)
H51C0.7963 (16)0.1651 (5)0.6050 (11)0.062*
H52C0.9226 (5)0.1824 (2)0.5496 (19)0.062*
H53C0.8195 (19)0.1518 (3)0.4787 (9)0.062*
C6C0.7449 (2)0.05019 (8)0.59555 (15)0.0142 (3)
C7C0.6754 (2)0.11008 (10)0.4427 (2)0.0141 (3)
H71C0.6122 (2)0.12501 (10)0.4938 (2)0.017*
C8C0.7366 (3)0.16011 (12)0.3817 (2)0.0182 (4)
H81C0.8059 (3)0.14473 (12)0.3381 (2)0.022*
C9C0.7866 (3)0.20363 (12)0.4632 (3)0.0329 (6)
H91C0.8303 (17)0.2335 (5)0.4236 (3)0.049*
H92C0.8422 (15)0.1846 (2)0.5138 (11)0.049*
H93C0.7193 (3)0.2206 (7)0.5041 (12)0.049*
C10C0.6476 (3)0.18839 (15)0.3040 (3)0.0298 (6)
H04C0.6291 (15)0.1624 (4)0.2438 (9)0.045*
H05C0.6837 (8)0.2233 (5)0.2749 (14)0.045*
H06C0.5726 (8)0.1977 (8)0.3432 (5)0.045*
C11C0.6167 (2)0.06821 (9)0.3613 (2)0.0167 (3)
O1D0.1999 (2)0.05945 (8)0.65968 (14)0.0314 (4)
O2D0.13878 (13)0.04529 (8)0.31782 (14)0.0260 (3)
O3D0.00423 (13)0.08325 (9)0.4221 (2)0.0379 (4)
N1D0.39797 (14)0.00299 (7)0.73896 (12)0.0174 (2)
H1D0.4656 (15)0.0182 (7)0.7539 (3)0.024 (4)*
H2D0.3317 (12)0.0135 (7)0.7709 (6)0.024 (4)*
H3D0.4079 (15)0.0389 (6)0.7659 (5)0.024 (4)*
N2D0.2948 (2)0.07719 (9)0.4985 (2)0.0153 (3)
H4D0.3614 (19)0.0726 (2)0.4610 (11)0.018*
C1D0.3794 (2)0.00576 (8)0.6180 (2)0.0147 (3)
H11D0.4573 (2)0.01643 (8)0.5813 (2)0.018*
C2D0.3363 (2)0.05240 (11)0.5763 (2)0.0187 (4)
H21D0.3010 (2)0.04746 (11)0.5026 (2)0.022*
H22D0.2709 (2)0.06638 (11)0.6248 (2)0.022*
C3D0.4366 (2)0.09766 (11)0.5705 (2)0.0203 (4)
H31D0.4895 (2)0.09388 (11)0.6364 (2)0.024*
C4D0.5148 (3)0.08852 (13)0.4685 (2)0.0267 (5)
H41D0.5428 (15)0.0490 (2)0.4661 (9)0.040*
H42D0.4665 (6)0.0967 (8)0.4032 (2)0.040*
H43D0.5852 (10)0.1140 (6)0.4709 (8)0.040*
C5D0.3818 (4)0.15675 (15)0.5696 (3)0.0359 (7)
H51D0.3410 (18)0.1639 (4)0.6392 (8)0.054*
H52D0.4463 (4)0.1849 (2)0.5589 (19)0.054*
H53D0.3228 (16)0.1596 (3)0.5100 (12)0.054*
C6D0.2828 (2)0.05080 (8)0.5949 (2)0.0160 (3)
C7D0.1979 (2)0.11364 (10)0.4547 (2)0.0152 (4)
H71D0.1561 (2)0.13255 (10)0.5174 (2)0.018*
C8D0.2520 (3)0.16030 (12)0.3810 (2)0.0180 (4)
H81D0.3065 (3)0.14196 (12)0.3261 (2)0.022*
C9D0.3275 (2)0.20190 (12)0.4498 (2)0.0292 (5)
H91D0.3925 (11)0.1811 (2)0.4871 (13)0.044*
H92D0.2751 (4)0.2202 (6)0.5040 (11)0.044*
H93D0.3632 (15)0.2309 (5)0.4023 (3)0.044*
C10D0.1511 (3)0.19223 (15)0.3205 (3)0.0304 (7)
H04D0.1146 (14)0.1671 (3)0.2658 (13)0.046*
H05D0.1854 (5)0.2257 (5)0.2843 (15)0.046*
H06D0.0888 (11)0.2043 (8)0.3726 (4)0.046*
C11D0.1038 (2)0.07731 (9)0.3937 (2)0.0168 (3)
O1G0.5025 (2)0.10857 (9)0.7971 (2)0.0368 (5)
H1G0.558 (4)0.0984 (16)0.738 (3)0.055*
C1G0.4704 (3)0.1593 (2)0.7467 (3)0.0456 (8)
H11G0.3992 (3)0.1756 (2)0.7847 (3)0.055*
H12G0.4462 (3)0.1513 (2)0.6705 (3)0.055*
C2G0.5711 (5)0.2020 (2)0.7466 (5)0.077 (2)
H21G0.5471 (15)0.2350 (7)0.703 (3)0.115*
H22G0.6443 (11)0.1849 (5)0.715 (3)0.115*
H23G0.588 (2)0.2141 (12)0.8215 (6)0.115*
O1H0.0060 (2)0.09470 (9)0.7821 (2)0.0275 (4)
H1H0.047 (3)0.0838 (15)0.748 (3)0.041*
C1H0.0179 (2)0.14497 (11)0.7205 (2)0.0297 (5)
H11H0.0983 (2)0.16211 (11)0.7352 (2)0.036*
H12H0.0140 (2)0.13547 (11)0.6420 (2)0.036*
C2H0.0804 (3)0.18807 (15)0.7469 (3)0.0432 (8)
H21H0.0717 (15)0.2212 (5)0.6991 (15)0.065*
H22H0.1604 (4)0.1708 (4)0.736 (2)0.065*
H23H0.0727 (15)0.2001 (8)0.8231 (7)0.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0183 (6)0.0293 (7)0.0258 (7)0.0061 (6)0.0080 (5)0.0055 (6)
O2A0.0175 (6)0.0331 (8)0.0361 (8)0.0005 (6)0.0057 (6)0.0196 (7)
O3A0.0122 (4)0.0319 (7)0.0232 (6)0.0020 (4)0.0023 (4)0.0105 (6)
N1A0.0169 (6)0.0180 (6)0.0168 (6)0.0000 (5)0.0009 (5)0.0020 (6)
N2A0.0115 (6)0.0205 (7)0.0173 (7)0.0030 (6)0.0013 (5)0.0015 (6)
C1A0.0119 (6)0.0168 (7)0.0141 (7)0.0005 (6)0.0008 (5)0.0015 (6)
C2A0.0171 (8)0.0154 (7)0.0212 (8)0.0003 (6)0.0024 (6)0.0047 (7)
C3A0.0292 (11)0.0188 (9)0.0268 (10)0.0051 (8)0.0073 (8)0.0044 (8)
C4A0.0237 (11)0.0338 (14)0.079 (3)0.0083 (10)0.0093 (14)0.008 (2)
C5A0.049 (2)0.0145 (10)0.056 (2)0.0006 (10)0.0052 (15)0.0079 (11)
C6A0.0130 (6)0.0148 (7)0.0183 (7)0.0003 (6)0.0008 (6)0.0031 (6)
C7A0.0167 (8)0.0156 (7)0.0160 (8)0.0026 (6)0.0004 (6)0.0025 (6)
C8A0.0212 (9)0.0166 (9)0.0252 (11)0.0002 (7)0.0027 (8)0.0022 (8)
C9A0.047 (2)0.0193 (9)0.0375 (14)0.0071 (10)0.0112 (12)0.0016 (9)
C10A0.0306 (13)0.0281 (13)0.0299 (13)0.0035 (10)0.0017 (10)0.0070 (10)
C11A0.0111 (6)0.0190 (8)0.0185 (8)0.0022 (5)0.0019 (6)0.0049 (7)
O1B0.0287 (7)0.0382 (9)0.0268 (8)0.0160 (7)0.0128 (6)0.0103 (7)
O2B0.0187 (6)0.0309 (8)0.0300 (8)0.0005 (6)0.0005 (6)0.0200 (7)
O3B0.0145 (6)0.0572 (11)0.0494 (10)0.0062 (6)0.0090 (6)0.0267 (10)
N1B0.0170 (6)0.0171 (6)0.0195 (7)0.0022 (5)0.0017 (5)0.0026 (6)
N2B0.0135 (7)0.0177 (7)0.0152 (6)0.0019 (5)0.0025 (5)0.0024 (5)
C1B0.0139 (6)0.0148 (6)0.0165 (7)0.0014 (6)0.0003 (6)0.0021 (6)
C2B0.0177 (8)0.0161 (8)0.0188 (8)0.0014 (6)0.0013 (6)0.0058 (7)
C3B0.0239 (10)0.0182 (8)0.0217 (9)0.0015 (7)0.0022 (7)0.0043 (7)
C4B0.0206 (9)0.0307 (11)0.0308 (11)0.0039 (8)0.0017 (8)0.0078 (10)
C5B0.050 (2)0.0155 (10)0.0406 (14)0.0029 (10)0.0047 (13)0.0033 (10)
C6B0.0125 (6)0.0178 (7)0.0183 (7)0.0019 (6)0.0024 (6)0.0014 (6)
C7B0.0120 (7)0.0147 (7)0.0160 (8)0.0018 (6)0.0005 (6)0.0032 (6)
C8B0.0215 (9)0.0173 (9)0.0206 (10)0.0005 (7)0.0017 (7)0.0002 (8)
C9B0.0383 (13)0.0223 (10)0.0341 (12)0.0106 (10)0.0080 (11)0.0005 (9)
C10B0.0316 (13)0.0252 (12)0.0373 (15)0.0021 (10)0.0053 (11)0.0075 (11)
C11B0.0118 (6)0.0198 (8)0.0190 (8)0.0012 (5)0.0002 (6)0.0027 (7)
O1E0.0301 (9)0.0289 (9)0.0404 (11)0.0003 (7)0.0071 (8)0.0082 (8)
C1E0.0374 (13)0.0283 (12)0.061 (2)0.0008 (10)0.0083 (13)0.0017 (12)
C2E0.059 (2)0.0288 (15)0.125 (4)0.0128 (14)0.031 (2)0.001 (2)
O1F0.0201 (7)0.0253 (8)0.0340 (9)0.0004 (6)0.0034 (6)0.0061 (7)
C1F0.0269 (10)0.0401 (14)0.0365 (13)0.0009 (9)0.0006 (9)0.0028 (11)
C2F0.052 (2)0.0246 (12)0.053 (2)0.0087 (11)0.0056 (14)0.0104 (12)
O1C0.0179 (5)0.0275 (7)0.0245 (7)0.0063 (5)0.0070 (5)0.0132 (6)
O2C0.0175 (6)0.0311 (8)0.0349 (8)0.0012 (6)0.0057 (6)0.0107 (7)
O3C0.0125 (5)0.0323 (7)0.0234 (6)0.0014 (4)0.0019 (4)0.0014 (6)
N1C0.0182 (6)0.0200 (6)0.0155 (6)0.0011 (5)0.0013 (5)0.0081 (6)
N2C0.0123 (6)0.0196 (7)0.0163 (6)0.0023 (6)0.0011 (5)0.0092 (5)
C1C0.0142 (6)0.0154 (7)0.0146 (7)0.0006 (6)0.0011 (6)0.0051 (6)
C2C0.0176 (9)0.0180 (8)0.0206 (8)0.0001 (7)0.0033 (7)0.0047 (7)
C3C0.0267 (11)0.0159 (8)0.0235 (9)0.0051 (7)0.0056 (8)0.0031 (7)
C4C0.0252 (11)0.0308 (14)0.080 (3)0.0076 (9)0.0140 (15)0.006 (2)
C5C0.053 (2)0.0197 (12)0.053 (2)0.0011 (11)0.003 (2)0.0003 (12)
C6C0.0127 (6)0.0149 (6)0.0151 (7)0.0008 (6)0.0011 (6)0.0059 (6)
C7C0.0101 (6)0.0170 (7)0.0150 (7)0.0021 (5)0.0007 (5)0.0065 (6)
C8C0.0213 (9)0.0153 (8)0.0181 (9)0.0005 (7)0.0000 (7)0.0073 (7)
C9C0.045 (2)0.0193 (9)0.0344 (12)0.0056 (10)0.0110 (12)0.0043 (9)
C10C0.0341 (14)0.0243 (12)0.0312 (13)0.0018 (10)0.0082 (10)0.0166 (10)
C11C0.0145 (6)0.0166 (8)0.0189 (9)0.0006 (5)0.0004 (6)0.0058 (7)
O1D0.0281 (7)0.0359 (9)0.0302 (8)0.0157 (7)0.0162 (7)0.0193 (7)
O2D0.0162 (6)0.0312 (8)0.0306 (8)0.0002 (5)0.0003 (6)0.0085 (7)
O3D0.0132 (5)0.0546 (11)0.0460 (10)0.0033 (6)0.0076 (6)0.0172 (9)
N1D0.0176 (6)0.0178 (6)0.0170 (6)0.0016 (5)0.0001 (5)0.0050 (5)
N2D0.0119 (6)0.0178 (7)0.0160 (6)0.0032 (5)0.0026 (5)0.0072 (5)
C1D0.0129 (6)0.0148 (6)0.0164 (7)0.0012 (6)0.0010 (6)0.0059 (6)
C2D0.0150 (8)0.0177 (8)0.0235 (9)0.0004 (6)0.0004 (6)0.0050 (7)
C3D0.0246 (10)0.0132 (8)0.0232 (9)0.0044 (7)0.0030 (7)0.0034 (7)
C4D0.0230 (9)0.0253 (11)0.0318 (11)0.0042 (8)0.0020 (8)0.0005 (9)
C5D0.044 (2)0.0187 (11)0.045 (2)0.0011 (10)0.0003 (13)0.0027 (11)
C6D0.0151 (7)0.0155 (7)0.0173 (7)0.0012 (6)0.0027 (6)0.0062 (6)
C7D0.0153 (7)0.0153 (8)0.0150 (8)0.0025 (6)0.0018 (6)0.0045 (6)
C8D0.0195 (9)0.0167 (9)0.0177 (9)0.0005 (7)0.0018 (7)0.0075 (7)
C9D0.0328 (12)0.0206 (9)0.0341 (12)0.0084 (9)0.0030 (10)0.0058 (9)
C10D0.0339 (14)0.0217 (11)0.0356 (14)0.0030 (10)0.0093 (11)0.0140 (10)
C11D0.0129 (6)0.0179 (8)0.0196 (8)0.0012 (5)0.0024 (6)0.0062 (7)
O1G0.0317 (9)0.0249 (9)0.0538 (13)0.0002 (7)0.0129 (9)0.0018 (9)
C1G0.0374 (14)0.047 (2)0.053 (2)0.0031 (12)0.0042 (13)0.0169 (15)
C2G0.068 (2)0.034 (2)0.128 (4)0.015 (2)0.048 (3)0.008 (2)
O1H0.0220 (7)0.0276 (9)0.0329 (9)0.0013 (6)0.0036 (6)0.0016 (7)
C1H0.0245 (9)0.0283 (11)0.0362 (12)0.0038 (8)0.0001 (8)0.0044 (10)
C2H0.0413 (15)0.0296 (14)0.059 (2)0.0041 (11)0.0046 (13)0.0069 (13)
Geometric parameters (Å, º) top
O1A—C6A1.240 (2)O1C—C6C1.233 (2)
O2A—C11A1.248 (2)O2C—C11C1.241 (3)
O3A—C11A1.263 (2)O3C—C11C1.269 (2)
N1A—C1A1.488 (2)N1C—C1C1.493 (2)
N1A—H1A0.884 (15)N1C—H1C0.91 (2)
N1A—H2A0.88 (2)N1C—H2C0.91 (2)
N1A—H3A0.884 (15)N1C—H3C0.91 (2)
N2A—C6A1.331 (3)N2C—C6C1.332 (3)
N2A—C7A1.451 (3)N2C—C7C1.465 (3)
N2A—H4A0.68 (3)N2C—H4C0.89 (3)
C1A—C6A1.525 (3)C1C—C6C1.532 (2)
C1A—C2A1.537 (3)C1C—C2C1.538 (3)
C1A—H11A1.00C1C—H11C1.00
C2A—C3A1.532 (4)C2C—C3C1.544 (3)
C2A—H21A0.99C2C—H21C0.99
C2A—H22A0.99C2C—H22C0.99
C3A—C4A1.511 (5)C3C—C5C1.514 (5)
C3A—C5A1.540 (5)C3C—C4C1.521 (4)
C3A—H31A1.00C3C—H31C1.00
C4A—H41A0.98C4C—H41C0.98
C4A—H42A0.98C4C—H42C0.98
C4A—H43A0.98C4C—H43C0.98
C5A—H51A0.98C5C—H51C0.98
C5A—H52A0.98C5C—H52C0.98
C5A—H53A0.98C5C—H53C0.98
C7A—C8A1.535 (4)C7C—C11C1.544 (3)
C7A—C11A1.547 (3)C7C—C8C1.548 (3)
C7A—H71A1.00C7C—H71C1.00
C8A—C10A1.525 (4)C8C—C10C1.520 (4)
C8A—C9A1.524 (4)C8C—C9C1.532 (4)
C8A—H81A1.00C8C—H81C1.00
C9A—H91A0.98C9C—H91C0.98
C9A—H92A0.98C9C—H92C0.98
C9A—H93A0.98C9C—H93C0.98
C10A—H04A0.98C10C—H04C0.98
C10A—H05A0.98C10C—H05C0.98
C10A—H06A0.98C10C—H06C0.98
O1B—C6B1.233 (2)O1D—C6D1.228 (2)
O2B—C11B1.261 (2)O2D—C11D1.257 (3)
O3B—C11B1.247 (2)O3D—C11D1.247 (2)
N1B—C1B1.492 (2)N1D—C1D1.499 (2)
N1B—H1B0.86 (2)N1D—H1D0.91 (2)
N1B—H2B0.86 (2)N1D—H2D0.91 (2)
N1B—H3B0.86 (2)N1D—H3D0.91 (2)
N2B—C6B1.340 (3)N2D—C6D1.342 (3)
N2B—C7B1.453 (3)N2D—C7D1.471 (3)
N2B—H4B0.75 (3)N2D—H4D0.87 (2)
C1B—C6B1.528 (3)C1D—C6D1.527 (2)
C1B—C2B1.538 (3)C1D—C2D1.536 (3)
C1B—H1CB1.00C1D—H11D1.00
C2B—C3B1.539 (3)C2D—C3D1.536 (3)
C2B—H21B0.99C2D—H21D0.99
C2B—H22B0.99C2D—H22D0.99
C3B—C4B1.523 (4)C3D—C5D1.515 (5)
C3B—C5B1.545 (4)C3D—C4D1.534 (4)
C3B—H31B1.00C3D—H31D1.00
C4B—H41B0.98C4D—H41D0.98
C4B—H42B0.98C4D—H42D0.98
C4B—H43B0.98C4D—H43D0.98
C5B—H51B0.98C5D—H51D0.98
C5B—H52B0.98C5D—H52D0.98
C5B—H53B0.98C5D—H53D0.98
C7B—C8B1.530 (4)C7D—C11D1.537 (3)
C7B—C11B1.539 (3)C7D—C8D1.542 (3)
C7B—H71B1.00C7D—H71D1.00
C8B—C9B1.523 (4)C8D—C9D1.537 (4)
C8B—C10B1.531 (4)C8D—C10D1.533 (4)
C8B—H81B1.00C8D—H81D1.00
C9B—H91B0.98C9D—H91D0.98
C9B—H92B0.98C9D—H92D0.98
C9B—H93B0.98C9D—H93D0.98
C10B—H04B0.98C10D—H04D0.98
C10B—H05B0.98C10D—H05D0.98
C10B—H06B0.98C10D—H06D0.98
O1E—C1E1.424 (4)O1G—C1G1.389 (4)
O1E—H1E0.83 (4)O1G—H1G0.98 (4)
C1E—C2E1.498 (5)C1G—C2G1.497 (6)
C1E—H11E0.99C1G—H11G0.99
C1E—H12E0.99C1G—H12G0.99
C2E—H21E0.98C2G—H21G0.98
C2E—H22E0.98C2G—H22G0.98
C2E—H23E0.98C2G—H23G0.98
O1F—C1F1.446 (4)O1H—C1H1.409 (3)
O1F—H1F0.79 (4)O1H—H1H0.76 (4)
C1F—C2F1.509 (4)C1H—C2H1.518 (4)
C1F—H11F0.99C1H—H11H0.99
C1F—H12F0.99C1H—H12H0.99
C2F—H21F0.98C2H—H21H0.98
C2F—H22F0.98C2H—H22H0.98
C2F—H23F0.98C2H—H23H0.98
C1A—N1A—H1A109.47 (9)C1C—N1C—H1C109.47 (10)
C1A—N1A—H2A109.47 (9)C1C—N1C—H2C109.47 (9)
H1A—N1A—H2A109.5H1C—N1C—H2C109.5
C1A—N1A—H3A109.47 (10)C1C—N1C—H3C109.47 (10)
H1A—N1A—H3A109.5H1C—N1C—H3C109.5
H2A—N1A—H3A109.5H2C—N1C—H3C109.5
C6A—N2A—C7A124.3 (2)C6C—N2C—C7C123.6 (2)
C6A—N2A—H4A117.85 (11)C6C—N2C—H4C118.18 (11)
C7A—N2A—H4A117.85 (12)C7C—N2C—H4C118.18 (11)
N1A—C1A—C6A108.42 (15)N1C—C1C—C6C107.63 (15)
N1A—C1A—C2A109.4 (2)N1C—C1C—C2C109.9 (2)
C6A—C1A—C2A109.0 (2)C6C—C1C—C2C108.5 (2)
N1A—C1A—H11A110.01 (9)N1C—C1C—H11C110.25 (9)
C6A—C1A—H11A110.01 (10)C6C—C1C—H11C110.25 (9)
C2A—C1A—H11A110.01 (11)C2C—C1C—H11C110.25 (11)
C3A—C2A—C1A114.8 (2)C1C—C2C—C3C114.9 (2)
C3A—C2A—H21A108.6 (2)C1C—C2C—H21C108.55 (11)
C1A—C2A—H21A108.57 (11)C3C—C2C—H21C108.55 (14)
C3A—C2A—H22A108.6 (2)C1C—C2C—H22C108.55 (12)
C1A—C2A—H22A108.57 (12)C3C—C2C—H22C108.55 (14)
H21A—C2A—H22A107.5H21C—C2C—H22C107.5
C4A—C3A—C2A112.4 (3)C5C—C3C—C4C110.2 (3)
C4A—C3A—C5A110.4 (3)C5C—C3C—C2C109.8 (2)
C2A—C3A—C5A109.6 (3)C4C—C3C—C2C110.8 (2)
C4A—C3A—H31A108.1 (2)C5C—C3C—H31C108.7 (2)
C2A—C3A—H31A108.1 (2)C4C—C3C—H31C108.7 (2)
C5A—C3A—H31A108.1 (2)C2C—C3C—H31C108.69 (14)
C3A—C4A—H41A109.5 (2)C3C—C4C—H41C109.5 (2)
C3A—C4A—H42A109.5 (2)C3C—C4C—H42C109.5 (2)
H41A—C4A—H42A109.5H41C—C4C—H42C109.5
C3A—C4A—H43A109.5 (2)C3C—C4C—H43C109.5 (2)
H41A—C4A—H43A109.5H41C—C4C—H43C109.5
H42A—C4A—H43A109.5H42C—C4C—H43C109.5
C3A—C5A—H51A109.5 (2)C3C—C5C—H51C109.5 (2)
C3A—C5A—H52A109.5 (2)C3C—C5C—H52C109.5 (2)
H51A—C5A—H52A109.5H51C—C5C—H52C109.5
C3A—C5A—H53A109.5 (2)C3C—C5C—H53C109.5 (2)
H51A—C5A—H53A109.5H51C—C5C—H53C109.5
H52A—C5A—H53A109.5H52C—C5C—H53C109.5
O1A—C6A—N2A124.5 (2)O1C—C6C—N2C124.6 (2)
O1A—C6A—C1A120.1 (2)O1C—C6C—C1C120.7 (2)
N2A—C6A—C1A115.3 (2)N2C—C6C—C1C114.5 (2)
N2A—C7A—C8A109.9 (2)N2C—C7C—C11C107.5 (2)
N2A—C7A—C11A107.7 (2)N2C—C7C—C8C109.2 (2)
C8A—C7A—C11A111.4 (2)C11C—C7C—C8C110.8 (2)
N2A—C7A—H71A109.27 (12)N2C—C7C—H71C109.78 (12)
C8A—C7A—H71A109.26 (14)C11C—C7C—H71C109.78 (11)
C11A—C7A—H71A109.26 (11)C8C—C7C—H71C109.78 (14)
C10A—C8A—C9A111.4 (3)C10C—C8C—C9C110.4 (3)
C10A—C8A—C7A111.5 (2)C10C—C8C—C7C110.8 (2)
C9A—C8A—C7A111.4 (2)C9C—C8C—C7C110.4 (2)
C10A—C8A—H81A107.4 (2)C10C—C8C—H81C108.4 (2)
C9A—C8A—H81A107.4 (2)C9C—C8C—H81C108.4 (2)
C7A—C8A—H81A107.43 (14)C7C—C8C—H81C108.38 (13)
C8A—C9A—H91A109.5 (2)C8C—C9C—H91C109.5 (2)
C8A—C9A—H92A109.5 (2)C8C—C9C—H92C109.47 (15)
H91A—C9A—H92A109.5H91C—C9C—H92C109.5
C8A—C9A—H93A109.5 (2)C8C—C9C—H93C109.5 (2)
H91A—C9A—H93A109.5H91C—C9C—H93C109.5
H92A—C9A—H93A109.5H92C—C9C—H93C109.5
C8A—C10A—H04A109.5 (2)C8C—C10C—H04C109.5 (2)
C8A—C10A—H05A109.5 (2)C8C—C10C—H05C109.5 (2)
H04A—C10A—H05A109.5H04C—C10C—H05C109.5
C8A—C10A—H06A109.5 (2)C8C—C10C—H06C109.5 (2)
H04A—C10A—H06A109.5H04C—C10C—H06C109.5
H05A—C10A—H06A109.5H05C—C10C—H06C109.5
O2A—C11A—O3A125.2 (2)O2C—C11C—O3C125.3 (2)
O2A—C11A—C7A117.1 (2)O2C—C11C—C7C117.4 (2)
O3A—C11A—C7A117.8 (2)O3C—C11C—C7C117.3 (2)
C1B—N1B—H1B109.47 (9)C1D—N1D—H1D109.47 (9)
C1B—N1B—H2B109.47 (10)C1D—N1D—H2D109.47 (9)
H1B—N1B—H2B109.5H1D—N1D—H2D109.5
C1B—N1B—H3B109.47 (10)C1D—N1D—H3D109.47 (10)
H1B—N1B—H3B109.5H1D—N1D—H3D109.5
H2B—N1B—H3B109.5H2D—N1D—H3D109.5
C6B—N2B—C7B122.1 (2)C6D—N2D—C7D121.3 (2)
C6B—N2B—H4B118.95 (11)C6D—N2D—H4D119.33 (11)
C7B—N2B—H4B118.95 (12)C7D—N2D—H4D119.33 (11)
N1B—C1B—C6B108.08 (15)N1D—C1D—C6D108.0 (2)
N1B—C1B—C2B108.9 (2)N1D—C1D—C2D109.5 (2)
C6B—C1B—C2B109.7 (2)C6D—C1D—C2D109.9 (2)
N1B—C1B—H1CB110.05 (9)N1D—C1D—H11D109.82 (9)
C6B—C1B—H1CB110.05 (10)C6D—C1D—H11D109.82 (10)
C2B—C1B—H1CB110.05 (11)C2D—C1D—H11D109.82 (11)
C3B—C2B—C1B113.3 (2)C1D—C2D—C3D114.2 (2)
C3B—C2B—H21B108.91 (14)C1D—C2D—H21D108.70 (12)
C1B—C2B—H21B108.91 (12)C3D—C2D—H21D108.71 (15)
C3B—C2B—H22B108.90 (14)C1D—C2D—H22D108.70 (12)
C1B—C2B—H22B108.91 (12)C3D—C2D—H22D108.70 (14)
H21B—C2B—H22B107.7H21D—C2D—H22D107.6
C4B—C3B—C2B111.7 (2)C5D—C3D—C4D110.3 (3)
C4B—C3B—C5B110.5 (2)C5D—C3D—C2D110.4 (2)
C2B—C3B—C5B109.1 (2)C4D—C3D—C2D110.2 (2)
C4B—C3B—H31B108.47 (15)C5D—C3D—H31D108.6 (2)
C2B—C3B—H31B108.47 (14)C4D—C3D—H31D108.64 (15)
C5B—C3B—H31B108.5 (2)C2D—C3D—H31D108.64 (15)
C3B—C4B—H41B109.5 (2)C3D—C4D—H41D109.5 (2)
C3B—C4B—H42B109.5 (2)C3D—C4D—H42D109.47 (15)
H41B—C4B—H42B109.5H41D—C4D—H42D109.5
C3B—C4B—H43B109.47 (15)C3D—C4D—H43D109.47 (14)
H41B—C4B—H43B109.5H41D—C4D—H43D109.5
H42B—C4B—H43B109.5H42D—C4D—H43D109.5
C3B—C5B—H51B109.5 (2)C3D—C5D—H51D109.5 (2)
C3B—C5B—H52B109.5 (2)C3D—C5D—H52D109.5 (2)
H51B—C5B—H52B109.5H51D—C5D—H52D109.5
C3B—C5B—H53B109.5 (2)C3D—C5D—H53D109.5 (2)
H51B—C5B—H53B109.5H51D—C5D—H53D109.5
H52B—C5B—H53B109.5H52D—C5D—H53D109.5
O1B—C6B—N2B124.5 (2)O1D—C6D—N2D124.5 (2)
O1B—C6B—C1B120.8 (2)O1D—C6D—C1D120.8 (2)
N2B—C6B—C1B114.7 (2)N2D—C6D—C1D114.6 (2)
N2B—C7B—C8B111.1 (2)N2D—C7D—C11D110.1 (2)
N2B—C7B—C11B110.5 (2)N2D—C7D—C8D110.4 (2)
C8B—C7B—C11B112.2 (2)C11D—C7D—C8D111.8 (2)
N2B—C7B—H71B107.60 (12)N2D—C7D—H71D108.17 (12)
C8B—C7B—H71B107.60 (13)C11D—C7D—H71D108.17 (11)
C11B—C7B—H71B107.60 (10)C8D—C7D—H71D108.17 (14)
C9B—C8B—C10B110.9 (3)C9D—C8D—C10D110.3 (3)
C9B—C8B—C7B110.6 (2)C9D—C8D—C7D109.9 (2)
C10B—C8B—C7B111.4 (2)C10D—C8D—C7D110.6 (2)
C9B—C8B—H81B107.9 (2)C9D—C8D—H81D108.7 (2)
C10B—C8B—H81B107.9 (2)C10D—C8D—H81D108.7 (2)
C7B—C8B—H81B107.94 (14)C7D—C8D—H81D108.66 (14)
C8B—C9B—H91B109.5 (2)C8D—C9D—H91D109.5 (2)
C8B—C9B—H92B109.5 (2)C8D—C9D—H92D109.47 (15)
H91B—C9B—H92B109.5H91D—C9D—H92D109.5
C8B—C9B—H93B109.5 (2)C8D—C9D—H93D109.47 (15)
H91B—C9B—H93B109.5H91D—C9D—H93D109.5
H92B—C9B—H93B109.5H92D—C9D—H93D109.5
C8B—C10B—H04B109.5 (2)C8D—C10D—H04D109.5 (2)
C8B—C10B—H05B109.5 (2)C8D—C10D—H05D109.5 (2)
H04B—C10B—H05B109.5H04D—C10D—H05D109.5
C8B—C10B—H06B109.5 (2)C8D—C10D—H06D109.5 (2)
H04B—C10B—H06B109.5H04D—C10D—H06D109.5
H05B—C10B—H06B109.5H05D—C10D—H06D109.5
O3B—C11B—O2B124.0 (2)O3D—C11D—O2D124.5 (2)
O3B—C11B—C7B116.8 (2)O3D—C11D—C7D116.4 (2)
O2B—C11B—C7B119.2 (2)O2D—C11D—C7D119.1 (2)
C1E—O1E—H1E107 (3)C1G—O1G—H1G92 (2)
O1E—C1E—C2E112.2 (3)O1G—C1G—C2G112.9 (4)
O1E—C1E—H11E109.2 (2)O1G—C1G—H11G109.0 (2)
C2E—C1E—H11E109.2 (2)C2G—C1G—H11G109.0 (2)
O1E—C1E—H12E109.2 (2)O1G—C1G—H12G109.0 (2)
C2E—C1E—H12E109.2 (3)C2G—C1G—H12G109.0 (3)
H11E—C1E—H12E107.9H11G—C1G—H12G107.8
C1E—C2E—H21E109.5 (3)C1G—C2G—H21G109.5 (3)
C1E—C2E—H22E109.5 (2)C1G—C2G—H22G109.5 (2)
H21E—C2E—H22E109.5H21G—C2G—H22G109.5
C1E—C2E—H23E109.5 (3)C1G—C2G—H23G109.5 (3)
H21E—C2E—H23E109.5H21G—C2G—H23G109.5
H22E—C2E—H23E109.5H22G—C2G—H23G109.5
C1F—O1F—H1F109 (2)C1H—O1H—H1H94 (3)
O1F—C1F—C2F112.5 (3)O1H—C1H—C2H112.3 (2)
O1F—C1F—H11F109.10 (14)O1H—C1H—H11H109.13 (14)
C2F—C1F—H11F109.1 (2)C2H—C1H—H11H109.1 (2)
O1F—C1F—H12F109.10 (14)O1H—C1H—H12H109.13 (14)
C2F—C1F—H12F109.1 (2)C2H—C1H—H12H109.1 (2)
H11F—C1F—H12F107.8H11H—C1H—H12H107.9
C1F—C2F—H21F109.5 (2)C1H—C2H—H21H109.5 (2)
C1F—C2F—H22F109.5 (2)C1H—C2H—H22H109.5 (2)
H21F—C2F—H22F109.5H21H—C2H—H22H109.5
C1F—C2F—H23F109.5 (2)C1H—C2H—H23H109.5 (2)
H21F—C2F—H23F109.5H21H—C2H—H23H109.5
H22F—C2F—H23F109.5H22H—C2H—H23H109.5
N1A—C1A—C2A—C3A73.5 (3)N1C—C1C—C2C—C3C72.5 (2)
C6A—C1A—C2A—C3A168.2 (2)C6C—C1C—C2C—C3C170.0 (2)
C1A—C2A—C3A—C4A72.6 (3)C1C—C2C—C3C—C5C166.5 (2)
C1A—C2A—C3A—C5A164.2 (3)C1C—C2C—C3C—C4C71.6 (3)
C7A—N2A—C6A—O1A12.9 (3)C7C—N2C—C6C—O1C13.3 (4)
C7A—N2A—C6A—C1A162.9 (2)C7C—N2C—C6C—C1C162.3 (2)
N1A—C1A—C6A—O1A33.0 (2)N1C—C1C—C6C—O1C32.7 (2)
C2A—C1A—C6A—O1A86.0 (2)C2C—C1C—C6C—O1C86.2 (2)
N1A—C1A—C6A—N2A151.0 (2)N1C—C1C—C6C—N2C151.5 (2)
C2A—C1A—C6A—N2A90.0 (2)C2C—C1C—C6C—N2C89.6 (2)
C6A—N2A—C7A—C8A150.9 (2)C6C—N2C—C7C—C11C88.4 (3)
C6A—N2A—C7A—C11A87.6 (3)C6C—N2C—C7C—C8C151.3 (2)
N2A—C7A—C8A—C10A170.7 (2)N2C—C7C—C8C—C10C171.5 (2)
C11A—C7A—C8A—C10A51.4 (3)C11C—C7C—C8C—C10C53.3 (3)
N2A—C7A—C8A—C9A64.1 (3)N2C—C7C—C8C—C9C65.8 (3)
C11A—C7A—C8A—C9A176.5 (2)C11C—C7C—C8C—C9C175.9 (2)
N2A—C7A—C11A—O2A54.8 (3)N2C—C7C—C11C—O2C54.2 (2)
C8A—C7A—C11A—O2A65.7 (3)C8C—C7C—C11C—O2C65.0 (3)
N2A—C7A—C11A—O3A125.6 (2)N2C—C7C—C11C—O3C126.0 (2)
C8A—C7A—C11A—O3A113.9 (2)C8C—C7C—C11C—O3C114.8 (2)
N1B—C1B—C2B—C3B76.9 (2)N1D—C1D—C2D—C3D75.3 (2)
C6B—C1B—C2B—C3B165.0 (2)C6D—C1D—C2D—C3D166.3 (2)
C1B—C2B—C3B—C4B77.4 (3)C1D—C2D—C3D—C5D159.3 (2)
C1B—C2B—C3B—C5B160.0 (2)C1D—C2D—C3D—C4D78.7 (3)
C7B—N2B—C6B—O1B10.3 (3)C7D—N2D—C6D—O1D9.0 (4)
C7B—N2B—C6B—C1B168.1 (2)C7D—N2D—C6D—C1D168.4 (2)
N1B—C1B—C6B—O1B30.4 (3)N1D—C1D—C6D—O1D32.3 (3)
C2B—C1B—C6B—O1B88.3 (2)C2D—C1D—C6D—O1D87.0 (3)
N1B—C1B—C6B—N2B151.1 (2)N1D—C1D—C6D—N2D150.2 (2)
C2B—C1B—C6B—N2B90.2 (2)C2D—C1D—C6D—N2D90.5 (2)
C6B—N2B—C7B—C8B149.5 (2)C6D—N2D—C7D—C11D84.8 (3)
C6B—N2B—C7B—C11B85.2 (2)C6D—N2D—C7D—C8D151.4 (2)
N2B—C7B—C8B—C9B66.8 (3)N2D—C7D—C8D—C9D67.3 (3)
C11B—C7B—C8B—C9B168.9 (2)C11D—C7D—C8D—C9D169.9 (2)
N2B—C7B—C8B—C10B169.4 (2)N2D—C7D—C8D—C10D170.8 (2)
C11B—C7B—C8B—C10B45.2 (3)C11D—C7D—C8D—C10D47.9 (3)
N2B—C7B—C11B—O3B125.4 (2)N2D—C7D—C11D—O3D126.7 (2)
C8B—C7B—C11B—O3B110.0 (2)C8D—C7D—C11D—O3D110.3 (2)
N2B—C7B—C11B—O2B56.1 (3)N2D—C7D—C11D—O2D55.2 (3)
C8B—C7B—C11B—O2B68.5 (3)C8D—C7D—C11D—O2D67.8 (3)
(lv2p) L-leucyl-L-valine 2-propanol (1:1) top
Crystal data top
C14H30N2O4F(000) = 640
Mr = 290.40Dx = 1.138 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 5.1709 (1) ÅCell parameters from 7127 reflections
b = 14.6136 (2) ŵ = 0.08 mm1
c = 22.4230 (4) ÅT = 150 K
V = 1694.40 (5) Å3Block, colourless
Z = 40.55 × 0.25 × 0.10 mm
Data collection top
Siemens SMART CCD
diffractometer
12521 independent reflections
Radiation source: fine-focus sealed tube9601 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Sets of exposures each taken over 0.6° ω rotation scansθmax = 43.2°, θmin = 2.3°
Absorption correction: multiscan (SADABS; sheldrick, 1996)
?
h = 97
Tmin = 0.952, Tmax = 0.980k = 2828
32534 measured reflectionsl = 4336
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.11Calculated w = 1/[σ2(Fo2) + (0.0524P)2 + 0.1584P]
where P = (Fo2 + 2Fc2)/3
12521 reflections(Δ/σ)max = 0.007
230 parametersΔρmax = 0.34 e Å3
3 restraintsΔρmin = 0.23 e Å3
Crystal data top
C14H30N2O4V = 1694.40 (5) Å3
Mr = 290.40Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.1709 (1) ŵ = 0.08 mm1
b = 14.6136 (2) ÅT = 150 K
c = 22.4230 (4) Å0.55 × 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 = 0.980Rint = 0.034
32534 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0563 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.34 e Å3
12521 reflectionsΔρmin = 0.23 e Å3
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
xyzUiso*/UeqOcc. (<1)
O1A0.4131 (2)0.46498 (4)0.20213 (4)0.0324 (2)
O2A0.4223 (5)0.8049 (3)0.2105 (3)0.0306 (6)0.50
O2B0.4895 (5)0.8032 (3)0.2117 (2)0.0272 (5)0.50
O3A0.7834 (4)0.72478 (11)0.22477 (10)0.0270 (3)0.50
O3B0.7750 (4)0.69564 (12)0.23718 (9)0.0274 (3)0.50
N1A0.0110 (6)0.38369 (12)0.2450 (2)0.0207 (5)0.50
H1A0.122 (3)0.3575 (5)0.2660 (8)0.031*0.50
H2A0.163 (3)0.3553 (5)0.2545 (8)0.031*0.50
H3A0.020 (4)0.37752 (15)0.2050 (6)0.031*0.50
N1B0.0467 (6)0.38817 (13)0.2423 (2)0.0185 (5)0.50
H1B0.192 (3)0.3715 (5)0.2620 (7)0.028*0.50
H2B0.083 (2)0.3490 (6)0.2513 (8)0.028*0.50
H3B0.077 (4)0.3868 (3)0.2026 (6)0.028*0.50
N2A0.23957 (12)0.60838 (4)0.20816 (3)0.01726 (10)
H4A0.109 (3)0.6381 (9)0.2167 (6)0.021*
C1A0.02897 (15)0.48323 (4)0.26047 (3)0.01735 (11)
H11A0.13819 (15)0.51571 (4)0.25306 (3)0.021*
C2A0.1100 (2)0.48923 (6)0.32621 (3)0.02267 (13)
H21A0.1946 (2)0.54909 (6)0.33308 (3)0.027*
H22A0.2395 (2)0.44092 (6)0.33432 (3)0.027*
C3A0.1152 (2)0.47873 (6)0.37079 (4)0.02484 (14)
H31A0.2327 (2)0.42915 (6)0.35627 (4)0.030*
C4A0.2691 (2)0.56778 (8)0.37477 (5)0.0327 (2)
H41A0.3336 (18)0.5842 (4)0.33510 (10)0.049 (3)*
H42A0.1569 (6)0.6167 (2)0.3898 (5)0.049 (3)*
H43A0.4154 (12)0.5595 (2)0.4020 (4)0.049 (3)*
C5A0.0140 (3)0.45234 (10)0.43247 (5)0.0457 (3)
H51A0.065 (2)0.3915 (4)0.43060 (12)0.053 (3)*
H52A0.1578 (5)0.4515 (7)0.46095 (12)0.053 (3)*
H53A0.1153 (16)0.4971 (5)0.4454 (2)0.053 (3)*
C6A0.24422 (15)0.51885 (5)0.21990 (3)0.01800 (11)
C7A0.43577 (14)0.65232 (5)0.17033 (3)0.01706 (11)
H71A0.57409 (14)0.60681 (5)0.16076 (3)0.020*
C8A0.3138 (2)0.68647 (6)0.11192 (4)0.02339 (14)
H81A0.1695 (2)0.72942 (6)0.12186 (4)0.028*
C9A0.2032 (2)0.60580 (8)0.07652 (4)0.0361 (2)
H91A0.1272 (19)0.62829 (12)0.0393 (2)0.050 (3)*
H92A0.0696 (15)0.5752 (5)0.1002 (2)0.050 (3)*
H93A0.3420 (5)0.5623 (4)0.0674 (4)0.050 (3)*
C10A0.5134 (2)0.73759 (8)0.07444 (5)0.0365 (2)
H04A0.4351 (7)0.7561 (7)0.0365 (2)0.062 (3)*
H05A0.6615 (11)0.6975 (3)0.0667 (5)0.062 (3)*
H06A0.5718 (18)0.7921 (5)0.0961 (2)0.062 (3)*
C11A0.5580 (3)0.73442 (9)0.20341 (7)0.0168 (2)*0.50
C11B0.5772 (3)0.72276 (9)0.21090 (7)0.0168 (2)*0.50
O1C0.79845 (15)0.42531 (5)0.12635 (3)0.03048 (14)
H1C0.658 (4)0.4386 (12)0.1460 (8)0.046*
C1C0.6655 (3)0.26692 (8)0.11978 (7)0.0483 (3)
H11C0.5156 (15)0.2794 (2)0.1452 (4)0.059 (3)*
H12C0.8120 (9)0.2480 (5)0.1446 (4)0.059 (3)*
H13C0.623 (2)0.2179 (3)0.09162 (7)0.059 (3)*
C2C0.7370 (2)0.35291 (7)0.08548 (4)0.0307 (2)
H21C0.5866 (2)0.37198 (7)0.06036 (4)0.037*
C3C0.9697 (3)0.33978 (13)0.04605 (7)0.0551 (4)
H31C1.0064 (17)0.3968 (3)0.0247 (5)0.081 (4)*
H32C0.9348 (11)0.2909 (7)0.0172 (4)0.081 (4)*
H33C1.1193 (7)0.3231 (10)0.07057 (10)0.081 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0348 (3)0.0226 (2)0.0399 (4)0.0137 (2)0.0183 (3)0.0097 (2)
O2A0.0251 (12)0.0195 (6)0.0472 (11)0.0065 (10)0.0025 (13)0.0104 (6)
O2B0.0286 (12)0.0147 (6)0.0384 (9)0.0032 (10)0.0045 (13)0.0047 (5)
O3A0.0177 (6)0.0227 (6)0.0406 (10)0.0019 (6)0.0056 (6)0.0083 (6)
O3B0.0182 (6)0.0278 (7)0.0362 (8)0.0042 (7)0.0037 (6)0.0065 (7)
N1A0.0256 (14)0.0118 (6)0.0247 (9)0.0015 (6)0.0057 (12)0.0019 (6)
N1B0.0210 (11)0.0136 (6)0.0207 (7)0.0041 (5)0.0031 (10)0.0003 (5)
N2A0.0153 (2)0.0141 (2)0.0224 (2)0.0008 (2)0.0041 (2)0.0003 (2)
C1A0.0194 (3)0.0141 (2)0.0186 (2)0.0003 (2)0.0020 (2)0.0011 (2)
C2A0.0200 (3)0.0289 (3)0.0191 (3)0.0030 (3)0.0011 (2)0.0008 (3)
C3A0.0287 (4)0.0263 (3)0.0195 (3)0.0031 (3)0.0044 (3)0.0013 (3)
C4A0.0269 (4)0.0377 (4)0.0336 (4)0.0053 (4)0.0064 (4)0.0041 (4)
C5A0.0552 (7)0.0605 (7)0.0215 (4)0.0168 (6)0.0063 (4)0.0081 (4)
C6A0.0185 (3)0.0159 (2)0.0196 (2)0.0028 (2)0.0028 (2)0.0021 (2)
C7A0.0158 (3)0.0147 (2)0.0207 (3)0.0002 (2)0.0033 (2)0.0005 (2)
C8A0.0224 (3)0.0251 (3)0.0227 (3)0.0021 (3)0.0009 (3)0.0048 (3)
C9A0.0432 (6)0.0418 (5)0.0234 (4)0.0135 (5)0.0050 (4)0.0008 (4)
C10A0.0399 (5)0.0398 (5)0.0299 (4)0.0109 (4)0.0058 (4)0.0106 (4)
O1C0.0278 (3)0.0271 (3)0.0365 (3)0.0018 (2)0.0105 (3)0.0036 (3)
C1C0.0631 (9)0.0321 (5)0.0498 (7)0.0130 (5)0.0020 (6)0.0065 (5)
C2C0.0234 (4)0.0393 (4)0.0294 (4)0.0023 (3)0.0008 (3)0.0047 (3)
C3C0.0437 (7)0.0791 (10)0.0426 (6)0.0062 (7)0.0163 (6)0.0240 (7)
Geometric parameters (Å, º) top
O1A—C6A1.2414 (9)C5A—H51A0.98
O2A—C11A1.256 (4)C5A—H52A0.98
O2B—C11B1.260 (4)C5A—H53A0.98
O3A—C11A1.268 (3)C7A—C8A1.5370 (11)
O3B—C11B1.245 (3)C7A—C11A1.5457 (13)
N1A—C1A1.4984 (14)C7A—C11B1.5563 (13)
N1A—H1A0.915 (13)C7A—H71A1.00
N1A—H2A0.915 (13)C8A—C10A1.5264 (13)
N1A—H3A0.915 (13)C8A—C9A1.5319 (14)
N1B—C1A1.4999 (14)C8A—H81A1.00
N1B—H1B0.903 (13)C9A—H91A0.98
N1B—H2B0.903 (13)C9A—H92A0.98
N1B—H3B0.903 (13)C9A—H93A0.98
N2A—C6A1.3348 (9)C10A—H04A0.98
N2A—C7A1.4701 (9)C10A—H05A0.98
N2A—H4A0.827 (14)C10A—H06A0.98
C1A—C6A1.5289 (10)O1C—C2C1.4354 (12)
C1A—C2A1.5349 (11)O1C—H1C0.87 (2)
C1A—H11A1.00C1C—C2C1.519 (2)
C2A—C3A1.5425 (12)C1C—H11C0.98
C2A—H21A0.99C1C—H12C0.98
C2A—H22A0.99C1C—H13C0.98
C3A—C4A1.5279 (14)C2C—C3C1.505 (2)
C3A—C5A1.5281 (14)C2C—H21C1.00
C3A—H31A1.00C3C—H31C0.98
C4A—H41A0.98C3C—H32C0.98
C4A—H42A0.98C3C—H33C0.98
C4A—H43A0.98
C1A—N1A—H1A109.5 (2)N2A—C7A—C11A110.14 (8)
C1A—N1A—H2A109.47 (12)C8A—C7A—C11A108.95 (8)
H1A—N1A—H2A109.5N2A—C7A—C11B106.01 (8)
C1A—N1A—H3A109.5 (2)C8A—C7A—C11B118.44 (8)
H1A—N1A—H3A109.5N2A—C7A—H71A109.07 (3)
H2A—N1A—H3A109.5C8A—C7A—H71A109.07 (4)
C1A—N1B—H1B109.5 (2)C11A—C7A—H71A109.07 (7)
C1A—N1B—H2B109.47 (12)C10A—C8A—C9A110.11 (8)
H1B—N1B—H2B109.5C10A—C8A—C7A110.52 (7)
C1A—N1B—H3B109.5 (2)C9A—C8A—C7A110.17 (7)
H1B—N1B—H3B109.5C10A—C8A—H81A108.66 (6)
H2B—N1B—H3B109.5C9A—C8A—H81A108.66 (6)
C6A—N2A—C7A121.98 (6)C7A—C8A—H81A108.66 (4)
C6A—N2A—H4A119.0 (9)C8A—C9A—H91A109.47 (5)
C7A—N2A—H4A118.0 (9)C8A—C9A—H92A109.47 (5)
N1A—C1A—C6A103.8 (2)H91A—C9A—H92A109.5
N1B—C1A—C6A110.1 (2)C8A—C9A—H93A109.47 (6)
N1A—C1A—C2A107.1 (2)H91A—C9A—H93A109.5
N1B—C1A—C2A112.7 (2)H92A—C9A—H93A109.5
C6A—C1A—C2A110.68 (6)C8A—C10A—H04A109.47 (6)
N1A—C1A—H11A111.63 (12)C8A—C10A—H05A109.47 (6)
C6A—C1A—H11A111.63 (4)H04A—C10A—H05A109.5
C2A—C1A—H11A111.63 (4)C8A—C10A—H06A109.47 (6)
C1A—C2A—C3A114.24 (7)H04A—C10A—H06A109.5
C1A—C2A—H21A108.70 (4)H05A—C10A—H06A109.5
C3A—C2A—H21A108.70 (5)O2A—C11A—O3A123.8 (2)
C1A—C2A—H22A108.70 (4)O2A—C11A—C7A118.0 (2)
C3A—C2A—H22A108.70 (5)O3A—C11A—C7A118.09 (13)
H21A—C2A—H22A107.6O3B—C11B—O2B125.8 (2)
C4A—C3A—C5A109.89 (8)O3B—C11B—C7A116.88 (14)
C4A—C3A—C2A110.26 (8)O2B—C11B—C7A117.2 (2)
C5A—C3A—C2A110.69 (9)C2C—O1C—H1C107.6 (11)
C4A—C3A—H31A108.65 (6)C2C—C1C—H11C109.47 (7)
C5A—C3A—H31A108.65 (7)C2C—C1C—H12C109.47 (8)
C2A—C3A—H31A108.65 (5)H11C—C1C—H12C109.5
C3A—C4A—H41A109.47 (5)C2C—C1C—H13C109.47 (6)
C3A—C4A—H42A109.47 (6)H11C—C1C—H13C109.5
H41A—C4A—H42A109.5H12C—C1C—H13C109.5
C3A—C4A—H43A109.47 (5)O1C—C2C—C3C106.98 (9)
H41A—C4A—H43A109.5O1C—C2C—C1C109.91 (9)
H42A—C4A—H43A109.5C3C—C2C—C1C112.74 (12)
C3A—C5A—H51A109.47 (6)O1C—C2C—H21C109.05 (5)
C3A—C5A—H52A109.47 (6)C3C—C2C—H21C109.05 (8)
H51A—C5A—H52A109.5C1C—C2C—H21C109.05 (8)
C3A—C5A—H53A109.47 (7)C2C—C3C—H31C109.47 (9)
H51A—C5A—H53A109.5C2C—C3C—H32C109.47 (7)
H52A—C5A—H53A109.5H31C—C3C—H32C109.5
O1A—C6A—N2A124.82 (7)C2C—C3C—H33C109.47 (8)
O1A—C6A—C1A119.15 (6)H31C—C3C—H33C109.5
N2A—C6A—C1A115.98 (6)H32C—C3C—H33C109.5
N2A—C7A—C8A110.50 (6)
N1A—C1A—C2A—C3A82.5 (2)C11A—C7A—C8A—C10A55.17 (11)
N1B—C1A—C2A—C3A71.2 (2)C11B—C7A—C8A—C10A53.79 (12)
C6A—C1A—C2A—C3A165.05 (7)N2A—C7A—C8A—C9A61.79 (9)
C1A—C2A—C3A—C4A77.88 (9)C11A—C7A—C8A—C9A177.07 (10)
C1A—C2A—C3A—C5A160.31 (9)C11B—C7A—C8A—C9A175.70 (10)
C7A—N2A—C6A—O1A2.03 (13)N2A—C7A—C11A—O2A71.5 (3)
C7A—N2A—C6A—C1A179.37 (6)C8A—C7A—C11A—O2A49.8 (3)
N1A—C1A—C6A—O1A26.0 (2)C11B—C7A—C11A—O2A137.5 (9)
N1B—C1A—C6A—O1A36.6 (2)N2A—C7A—C11A—O3A104.4 (2)
C2A—C1A—C6A—O1A88.61 (9)C8A—C7A—C11A—O3A134.3 (2)
N1A—C1A—C6A—N2A156.5 (2)C11B—C7A—C11A—O3A38.4 (7)
N1B—C1A—C6A—N2A145.9 (2)N2A—C7A—C11B—O3B92.0 (2)
C2A—C1A—C6A—N2A88.89 (8)C8A—C7A—C11B—O3B143.2 (2)
C6A—N2A—C7A—C8A112.83 (8)C11A—C7A—C11B—O3B151.1 (9)
C6A—N2A—C7A—C11A126.74 (9)N2A—C7A—C11B—O2B91.6 (3)
C6A—N2A—C7A—C11B117.65 (9)C8A—C7A—C11B—O2B33.1 (3)
N2A—C7A—C8A—C10A176.30 (7)C11A—C7A—C11B—O2B25.2 (7)

Experimental details

(lvm)(lve)(lv2p)
Crystal data
Chemical formulaC12H26N2O4C13H28N2O4C14H30N2O4
Mr262.35276.37290.40
Crystal system, space groupMonoclinic, P21Monoclinic, P21Orthorhombic, P212121
Temperature (K)150150150
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), 9090, 90.0121 (8), 9090, 90, 90
V3)766.87 (1)3175.88 (4)1694.40 (5)
Z284
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.080.090.08
Crystal size (mm)0.50 × 0.40 × 0.350.60 × 0.50 × 0.250.55 × 0.25 × 0.10
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Siemens SMART CCD
diffractometer
Siemens SMART CCD
diffractometer
Absorption correctionMultiscan (SADABS; Sheldrick, 1996)Multiscan (SADABS; Sheldrick, 1996)Multiscan (SADABS; Sheldrick, 1996)
Tmin, Tmax0.959, 0.9710.950, 0.9790.952, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
17325, 12154, 8119 50343, 38561, 28178 32534, 12521, 9601
Rint0.0490.0390.034
(sin θ/λ)max1)1.0740.9620.962
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 reflections121533856112521
No. of parameters203734230
No. of restraints113
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.64, 0.280.54, 0.320.34, 0.23
Absolute structure?Flack H D (1983), Acta Cryst. A39, 876-881?
Absolute structure parameter?0.24 (45)?

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXS86 (Sheldrick, 1990), SHELXTL (Sheldrick, 1994).

Table 3. Selected bond lengths (Å) bond angles (°) and torsion angles (°) for L-Leu-L-Val alcohol solvates top
LVMLVELV2P
AABCDAB
N1-C11.4863 (11)1.488 (2)1.492 (2)1.493 (2)1.499 (2)1.4984 (14)1.4999 (14)
N2-C61.3316 (11)1.331 (3)1.340 (3)1.332 (3)1.342 (3)1.3348 (9)
O1-C61.2394 (11)1.240 (2)1.233 (2)1.233 (2)1.228 (2)1.2414 (9)
O2-C111.2495 (11)1.248 (2)1.261 (2)1.241 (3)1.257 (3)1.256 (4)1.260 (3)
O3-C111.2599 (11)1.263 (2)1.247 (2)1.269 (2)1.247 (2)1.268 (3)1.245 (3)
C7-C111.5454 (12)1.547 (3)1.539 (3)1.544 (3)1.537 (3)1.5457 (13)1.5563 (13)
C3-C41.532 (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-C6108.01 (7)108.42 (15)108.08 (15)107.63 (15)108.0 (2)103.8 (2)110.1 (2)
C1-C6-N2114.36 (7)115.3 (2)114.7 (2)114.5 (2)114.6 (2)115.98 (6)
C6-N2-C7124.17 (7)124.3 (2)122.1 (2)123.6 (2)121.3 (2)121.98 (6)
N2-C7-C11107.16 (7)107.7 (2)110.5 (2)107.5 (2)110.1 (2)110.14 (8)106.01 (8)
O2-C11-O3125.37 (9)125.2 (2)124.0 (2)125.3 (2)124.5 (2)123.8 (2)125.8 (2)
C2-C3-C5108.59 (15)109.6 (3)109.1 (2)109.8 (2)110.4 (2)110.69 (9)
C9-C8-C10110.99 (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.
 
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