The structure of the primary amino acid L-leucine has been determined for the first time by neutron diffraction. This was made possible by the use of modern neutron Laue diffraction to overcome the previously prohibitive effects of crystal size and quality. The packing of the structure into hydrophobic and hydrophilic layers is explained by the intermolecular interaction energies calculated using the PIXEL method. Variable-temperature data collections confirmed the absence of phase transitions between 120 and 300 K in the single-crystal form.
Supporting information
CCDC references: 1508363; 1508364
For both compounds, data collection: MAATEL/ANSTO control program; cell refinement: LaueG (Piltz, 2011). Data reduction: argonne_boxes (Wilkinson et al., 1988) & LaueG (Piltz, 2011)' for leu_300; argonne_boxes (Wilkinson et al., 1988) & LaueG (Piltz, 2011) for leu_120. For both compounds, program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014).
(leu_300) 2-amino-4-methylpentanoic acid
top
Crystal data top
C6H13NO2 | Z = 4 |
Mr = 131.17 | F(000) = 288 |
Monoclinic, P21 | Dx = 1.165 Mg m−3 |
a = 9.606 (3) Å | Neutron radiation, λ = 0.80 Å |
b = 5.324 (7) Å | µ = 0.13 mm−1 |
c = 14.666 (2) Å | T = 300 K |
β = 94.06 (3)° | Plate, colourless |
V = 748.2 (10) Å3 | 2 × 0.5 × 0.2 mm |
Data collection top
KOALA diffractometer | Rint = 0.112 |
Laue scans | θmax = 71.4° |
24819 measured reflections | h = −19→19 |
1648 independent reflections | k = −7→7 |
1367 reflections with I > 2σ(I) | l = −12→12 |
Refinement top
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.0353P)2 + 6.3211P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.134 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.55 e Å−3 |
1647 reflections | Δρmin = −0.63 e Å−3 |
397 parameters | Absolute structure: Absolute structure known from synthesis |
361 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.2384 (3) | 0.4884 (7) | 0.6180 (2) | 0.0288 (7) | |
O1 | 0.1387 (4) | 0.6232 (9) | 0.5871 (3) | 0.0355 (10) | |
O2 | 0.2300 (5) | 0.2611 (10) | 0.6362 (4) | 0.0464 (12) | |
C2 | 0.3798 (3) | 0.6203 (7) | 0.6367 (2) | 0.0278 (7) | |
N1 | 0.3885 (3) | 0.8406 (5) | 0.57485 (18) | 0.0311 (6) | |
C3 | 0.3997 (4) | 0.7190 (9) | 0.7349 (3) | 0.0385 (9) | |
C4 | 0.4057 (5) | 0.5193 (12) | 0.8098 (3) | 0.0517 (11) | |
C5 | 0.5333 (7) | 0.3522 (14) | 0.8057 (5) | 0.0721 (16) | |
C6 | 0.4078 (11) | 0.658 (2) | 0.9035 (4) | 0.0843 (19) | |
C7 | 0.2532 (3) | 0.4009 (7) | 0.3867 (2) | 0.0279 (7) | |
O3 | 0.3469 (4) | 0.5525 (9) | 0.4141 (3) | 0.0352 (9) | |
O4 | 0.2665 (6) | 0.1690 (11) | 0.3817 (5) | 0.0525 (14) | |
C8 | 0.1136 (3) | 0.5157 (8) | 0.3521 (3) | 0.0324 (8) | |
N2 | 0.0874 (3) | 0.7497 (6) | 0.4056 (2) | 0.0391 (7) | |
C9 | 0.1115 (5) | 0.5906 (11) | 0.2518 (3) | 0.0508 (11) | |
C10 | 0.1137 (6) | 0.3740 (16) | 0.1839 (3) | 0.0677 (15) | |
C11 | −0.0254 (10) | 0.231 (2) | 0.1775 (6) | 0.091 (2) | |
C12 | 0.1427 (15) | 0.475 (3) | 0.0900 (5) | 0.122 (3) | |
H1 | 0.4627 (8) | 0.4897 (18) | 0.6210 (6) | 0.0464 (18) | |
H2 | 0.3220 (8) | 0.9803 (18) | 0.5910 (6) | 0.0451 (16) | |
H3 | 0.4915 (8) | 0.9138 (17) | 0.5793 (6) | 0.0432 (17) | |
H4 | 0.3639 (8) | 0.7819 (18) | 0.5076 (5) | 0.0465 (17) | |
H5 | 0.3177 (12) | 0.853 (2) | 0.7448 (7) | 0.065 (2) | |
H6 | 0.4982 (10) | 0.818 (2) | 0.7416 (6) | 0.057 (2) | |
H7 | 0.3127 (13) | 0.412 (3) | 0.8019 (8) | 0.080 (3) | |
H8 | 0.6254 (16) | 0.454 (3) | 0.8161 (13) | 0.097 (4) | |
H9 | 0.530 (2) | 0.256 (4) | 0.7459 (12) | 0.097 (4) | |
H10 | 0.535 (2) | 0.213 (4) | 0.8567 (13) | 0.106 (4) | |
H11 | 0.410 (2) | 0.528 (5) | 0.9577 (11) | 0.118 (5) | |
H12 | 0.496 (2) | 0.765 (4) | 0.9151 (11) | 0.108 (4) | |
H13 | 0.323 (2) | 0.771 (5) | 0.9099 (11) | 0.118 (5) | |
H14 | 0.0298 (8) | 0.387 (2) | 0.3641 (6) | 0.051 (2) | |
H15 | 0.1537 (9) | 0.8928 (19) | 0.3895 (7) | 0.0495 (18) | |
H16 | 0.1035 (9) | 0.7114 (19) | 0.4754 (6) | 0.0507 (18) | |
H17 | −0.0139 (9) | 0.813 (3) | 0.3940 (8) | 0.065 (3) | |
H18 | 0.1967 (14) | 0.718 (3) | 0.2437 (8) | 0.081 (3) | |
H19 | 0.0163 (13) | 0.705 (3) | 0.2369 (8) | 0.076 (3) | |
H20 | 0.1892 (18) | 0.241 (4) | 0.2079 (10) | 0.100 (4) | |
H21 | 0.147 (3) | 0.323 (6) | 0.0424 (13) | 0.155 (6) | |
H22 | 0.230 (3) | 0.584 (7) | 0.0922 (14) | 0.156 (7) | |
H23 | 0.059 (3) | 0.599 (7) | 0.0626 (15) | 0.151 (6) | |
H24 | −0.051 (3) | 0.162 (5) | 0.2422 (14) | 0.125 (5) | |
H25 | −0.026 (3) | 0.079 (5) | 0.1344 (14) | 0.123 (5) | |
H26 | −0.102 (2) | 0.341 (5) | 0.1548 (15) | 0.116 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0236 (14) | 0.0266 (18) | 0.0368 (17) | −0.0073 (13) | 0.0065 (12) | −0.0021 (14) |
O1 | 0.0199 (16) | 0.038 (3) | 0.048 (2) | −0.0043 (16) | 0.0012 (15) | 0.002 (2) |
O2 | 0.038 (2) | 0.032 (2) | 0.070 (3) | −0.0087 (19) | 0.003 (2) | 0.006 (2) |
C2 | 0.0192 (14) | 0.0283 (18) | 0.0360 (16) | −0.0043 (13) | 0.0028 (11) | −0.0019 (13) |
N1 | 0.0236 (11) | 0.0331 (15) | 0.0367 (13) | −0.0088 (11) | 0.0035 (9) | −0.0019 (11) |
C3 | 0.0386 (18) | 0.041 (2) | 0.0350 (17) | −0.0038 (17) | −0.0005 (14) | −0.0038 (15) |
C4 | 0.051 (2) | 0.065 (3) | 0.0386 (19) | −0.009 (2) | −0.0033 (16) | 0.0140 (19) |
C5 | 0.073 (3) | 0.061 (3) | 0.079 (4) | 0.011 (3) | −0.016 (2) | 0.005 (3) |
C6 | 0.100 (4) | 0.112 (5) | 0.040 (3) | 0.003 (4) | −0.005 (3) | −0.007 (3) |
C7 | 0.0212 (13) | 0.0267 (18) | 0.0357 (17) | 0.0028 (12) | 0.0018 (12) | −0.0022 (13) |
O3 | 0.0208 (16) | 0.034 (2) | 0.050 (2) | 0.0046 (15) | −0.0019 (15) | −0.0100 (18) |
O4 | 0.039 (2) | 0.030 (2) | 0.089 (4) | 0.0050 (19) | 0.001 (2) | −0.006 (2) |
C8 | 0.0200 (14) | 0.039 (2) | 0.0376 (16) | 0.0002 (14) | −0.0013 (11) | 0.0059 (15) |
N2 | 0.0283 (13) | 0.0420 (18) | 0.0477 (16) | 0.0154 (13) | 0.0064 (11) | 0.0083 (13) |
C9 | 0.051 (2) | 0.062 (3) | 0.0389 (19) | −0.011 (2) | −0.0053 (16) | 0.0121 (18) |
C10 | 0.062 (3) | 0.097 (4) | 0.043 (2) | −0.011 (3) | 0.0022 (19) | −0.012 (3) |
C11 | 0.092 (4) | 0.105 (5) | 0.075 (4) | −0.038 (4) | 0.005 (3) | −0.013 (4) |
C12 | 0.149 (7) | 0.179 (8) | 0.039 (3) | −0.054 (7) | 0.020 (3) | 0.002 (4) |
H1 | 0.030 (3) | 0.044 (4) | 0.065 (4) | 0.003 (3) | 0.004 (3) | −0.008 (4) |
H2 | 0.039 (3) | 0.039 (4) | 0.058 (4) | −0.003 (3) | 0.008 (3) | 0.002 (3) |
H3 | 0.034 (3) | 0.041 (4) | 0.055 (4) | −0.012 (3) | 0.004 (2) | 0.002 (3) |
H4 | 0.043 (3) | 0.052 (4) | 0.045 (3) | −0.009 (3) | 0.003 (2) | −0.005 (3) |
H5 | 0.072 (5) | 0.068 (6) | 0.055 (4) | 0.016 (4) | 0.009 (4) | −0.009 (4) |
H6 | 0.060 (4) | 0.062 (6) | 0.049 (4) | −0.019 (4) | −0.004 (3) | −0.007 (4) |
H7 | 0.077 (5) | 0.095 (7) | 0.068 (6) | −0.025 (5) | −0.011 (4) | 0.031 (5) |
H8 | 0.072 (5) | 0.083 (7) | 0.135 (11) | 0.014 (5) | −0.002 (5) | −0.008 (7) |
H9 | 0.116 (9) | 0.075 (8) | 0.098 (6) | 0.021 (7) | −0.012 (5) | −0.004 (5) |
H10 | 0.119 (10) | 0.089 (7) | 0.107 (7) | 0.013 (6) | −0.017 (6) | 0.022 (7) |
H11 | 0.148 (12) | 0.141 (9) | 0.064 (6) | −0.003 (8) | −0.004 (6) | 0.007 (6) |
H12 | 0.120 (7) | 0.126 (10) | 0.076 (8) | −0.008 (7) | −0.006 (5) | −0.019 (7) |
H13 | 0.126 (7) | 0.156 (11) | 0.071 (8) | 0.024 (8) | 0.003 (6) | −0.009 (7) |
H14 | 0.033 (3) | 0.062 (5) | 0.059 (4) | −0.007 (3) | −0.001 (3) | 0.012 (4) |
H15 | 0.047 (4) | 0.039 (4) | 0.062 (5) | 0.006 (3) | 0.007 (3) | 0.004 (3) |
H16 | 0.049 (4) | 0.050 (5) | 0.054 (4) | 0.011 (4) | 0.010 (3) | 0.007 (3) |
H17 | 0.038 (3) | 0.080 (6) | 0.076 (5) | 0.025 (4) | 0.008 (3) | 0.024 (5) |
H18 | 0.083 (5) | 0.100 (8) | 0.059 (5) | −0.041 (6) | −0.001 (4) | 0.018 (5) |
H19 | 0.074 (5) | 0.091 (8) | 0.062 (5) | 0.009 (5) | −0.010 (4) | 0.013 (5) |
H20 | 0.103 (7) | 0.124 (8) | 0.072 (6) | 0.015 (7) | 0.001 (5) | −0.018 (6) |
H21 | 0.190 (16) | 0.207 (12) | 0.068 (7) | −0.047 (10) | 0.019 (8) | −0.019 (8) |
H22 | 0.176 (9) | 0.221 (15) | 0.075 (9) | −0.075 (11) | 0.029 (7) | −0.008 (9) |
H23 | 0.180 (10) | 0.197 (13) | 0.075 (9) | −0.043 (10) | 0.003 (8) | 0.013 (9) |
H24 | 0.144 (12) | 0.136 (12) | 0.096 (6) | −0.046 (10) | 0.017 (6) | −0.005 (7) |
H25 | 0.149 (12) | 0.121 (8) | 0.099 (8) | −0.037 (7) | 0.003 (8) | −0.023 (7) |
H26 | 0.095 (6) | 0.127 (8) | 0.123 (11) | −0.037 (6) | −0.011 (6) | −0.014 (7) |
Geometric parameters (Å, º) top
C1—O2 | 1.243 (7) | C7—O4 | 1.244 (7) |
C1—O1 | 1.256 (6) | C7—O3 | 1.254 (6) |
C1—C2 | 1.536 (4) | C7—C8 | 1.527 (5) |
C2—H1 | 1.094 (9) | C8—H14 | 1.082 (9) |
C2—N1 | 1.489 (5) | C8—N2 | 1.503 (6) |
C2—C3 | 1.532 (5) | C8—C9 | 1.524 (6) |
N1—H2 | 1.019 (10) | N2—H15 | 1.032 (11) |
N1—H4 | 1.045 (8) | N2—H17 | 1.033 (8) |
N1—H3 | 1.061 (7) | N2—H16 | 1.044 (10) |
C3—H5 | 1.079 (12) | C9—H18 | 1.077 (13) |
C3—H6 | 1.081 (10) | C9—H19 | 1.108 (15) |
C3—C4 | 1.527 (7) | C9—C10 | 1.524 (9) |
C4—H7 | 1.059 (14) | C10—H20 | 1.05 (2) |
C4—C5 | 1.520 (9) | C10—C12 | 1.522 (10) |
C4—C6 | 1.558 (9) | C10—C11 | 1.537 (10) |
C5—H9 | 1.01 (2) | C11—H26 | 0.98 (4) |
C5—H8 | 1.04 (2) | C11—H25 | 1.02 (3) |
C5—H10 | 1.05 (2) | C11—H24 | 1.06 (3) |
C6—H13 | 1.02 (3) | C12—H22 | 1.02 (4) |
C6—H12 | 1.03 (3) | C12—H21 | 1.07 (3) |
C6—H11 | 1.05 (2) | C12—H23 | 1.09 (5) |
| | | |
O2—C1—O1 | 125.0 (4) | O4—C7—O3 | 125.7 (5) |
O2—C1—C2 | 118.5 (4) | O4—C7—C8 | 118.0 (4) |
O1—C1—C2 | 116.4 (4) | O3—C7—C8 | 116.2 (4) |
H1—C2—N1 | 107.4 (6) | H14—C8—N2 | 106.7 (6) |
H1—C2—C3 | 111.8 (6) | H14—C8—C9 | 111.3 (6) |
N1—C2—C3 | 107.1 (3) | N2—C8—C9 | 107.2 (4) |
H1—C2—C1 | 108.6 (6) | H14—C8—C7 | 109.8 (6) |
N1—C2—C1 | 109.8 (3) | N2—C8—C7 | 109.5 (3) |
C3—C2—C1 | 112.0 (3) | C9—C8—C7 | 112.1 (3) |
H2—N1—H4 | 109.5 (8) | H15—N2—H17 | 108.1 (9) |
H2—N1—H3 | 108.4 (8) | H15—N2—H16 | 108.5 (8) |
H4—N1—H3 | 108.4 (7) | H17—N2—H16 | 107.4 (8) |
H2—N1—C2 | 111.7 (5) | H15—N2—C8 | 111.3 (6) |
H4—N1—C2 | 108.7 (6) | H17—N2—C8 | 112.0 (8) |
H3—N1—C2 | 110.2 (5) | H16—N2—C8 | 109.3 (6) |
H5—C3—H6 | 107.9 (10) | H18—C9—H19 | 104.7 (13) |
H5—C3—C4 | 110.6 (7) | H18—C9—C8 | 108.3 (7) |
H6—C3—C4 | 106.7 (7) | H19—C9—C8 | 106.8 (8) |
H5—C3—C2 | 108.0 (7) | H18—C9—C10 | 111.1 (10) |
H6—C3—C2 | 107.6 (6) | H19—C9—C10 | 109.7 (9) |
C4—C3—C2 | 115.7 (4) | C8—C9—C10 | 115.6 (5) |
H7—C4—C5 | 110.9 (11) | H20—C10—C12 | 111.9 (12) |
H7—C4—C3 | 107.9 (7) | H20—C10—C9 | 109.3 (10) |
C5—C4—C3 | 111.6 (5) | C12—C10—C9 | 109.7 (8) |
H7—C4—C6 | 108.0 (9) | H20—C10—C11 | 105.2 (13) |
C5—C4—C6 | 110.6 (5) | C12—C10—C11 | 109.4 (7) |
C3—C4—C6 | 107.6 (6) | C9—C10—C11 | 111.3 (6) |
H9—C5—H8 | 111.1 (17) | H26—C11—H25 | 106.7 (19) |
H9—C5—H10 | 104.9 (17) | H26—C11—H24 | 107 (2) |
H8—C5—H10 | 107.1 (15) | H25—C11—H24 | 107 (2) |
H9—C5—C4 | 110.9 (11) | H26—C11—C10 | 110.7 (14) |
H8—C5—C4 | 111.7 (11) | H25—C11—C10 | 113.6 (15) |
H10—C5—C4 | 110.9 (13) | H24—C11—C10 | 111.6 (14) |
H13—C6—H12 | 108 (2) | H22—C12—H21 | 113 (2) |
H13—C6—H11 | 106.9 (19) | H22—C12—H23 | 104 (3) |
H12—C6—H11 | 105.7 (17) | H21—C12—H23 | 106 (2) |
H13—C6—C4 | 113.6 (11) | H22—C12—C10 | 112.0 (14) |
H12—C6—C4 | 111.6 (11) | H21—C12—C10 | 110.0 (17) |
H11—C6—C4 | 110.7 (14) | H23—C12—C10 | 111.6 (14) |
(leu_120) 2-amino-4-methylpentanoic acid
top
Crystal data top
C6H13NO2 | Z = 4 |
Mr = 131.17 | F(000) = 288 |
Monoclinic, P21 | Dx = 1.187 Mg m−3 |
a = 9.562 (2) Å | Neutron radiation, λ = 0.80 Å |
b = 5.301 (1) Å | µ = 0.0 mm−1 |
c = 14.519 (3) Å | T = 120 K |
β = 94.20 (2)° | Plate, colourless |
V = 734.0 (3) Å3 | 2 × 0.5 × 0.2 mm |
Data collection top
KOALA diffractometer | Rint = 0.156 |
Laue scans | θmax = 71.4° |
21729 measured reflections | h = −14→14 |
2430 independent reflections | k = −7→8 |
1955 reflections with I > 2σ(I) | l = −22→22 |
Refinement top
Refinement on F2 | 361 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.079 | All H-atom parameters refined |
wR(F2) = 0.171 | w = 1/[σ2(Fo2) + (0.0484P)2 + 12.6665P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max < 0.001 |
2429 reflections | Δρmax = 1.29 e Å−3 |
397 parameters | Δρmin = −1.40 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.2364 (3) | 0.5018 (7) | 0.6168 (2) | 0.0132 (6) | |
O1 | 0.1364 (4) | 0.6377 (9) | 0.5851 (3) | 0.0168 (7) | |
O2 | 0.2267 (4) | 0.2744 (8) | 0.6365 (3) | 0.0196 (8) | |
C2 | 0.3793 (3) | 0.6312 (7) | 0.6347 (2) | 0.0130 (6) | |
N1 | 0.3863 (2) | 0.8535 (5) | 0.57206 (16) | 0.0143 (4) | |
C3 | 0.4010 (4) | 0.7295 (7) | 0.7346 (2) | 0.0160 (6) | |
C4 | 0.4055 (4) | 0.5299 (8) | 0.8106 (3) | 0.0209 (7) | |
C5 | 0.5306 (5) | 0.3530 (9) | 0.8055 (3) | 0.0276 (8) | |
C6 | 0.4135 (5) | 0.6616 (11) | 0.9045 (3) | 0.0321 (9) | |
C7 | 0.2524 (3) | 0.3905 (7) | 0.3862 (2) | 0.0147 (6) | |
O3 | 0.3463 (4) | 0.5453 (8) | 0.4147 (3) | 0.0166 (7) | |
O4 | 0.2674 (5) | 0.1553 (9) | 0.3824 (3) | 0.0222 (8) | |
C8 | 0.1113 (3) | 0.5015 (7) | 0.3487 (2) | 0.0150 (6) | |
N2 | 0.0823 (3) | 0.7371 (5) | 0.39997 (18) | 0.0177 (5) | |
C9 | 0.1130 (4) | 0.5668 (8) | 0.2461 (3) | 0.0209 (7) | |
C10 | 0.1156 (4) | 0.3402 (11) | 0.1804 (3) | 0.0281 (8) | |
C11 | −0.0243 (6) | 0.2017 (11) | 0.1749 (4) | 0.0367 (11) | |
C12 | 0.1500 (7) | 0.4288 (16) | 0.0852 (3) | 0.0513 (16) | |
H1 | 0.4639 (8) | 0.5013 (16) | 0.6190 (6) | 0.0262 (13) | |
H2 | 0.3205 (8) | 0.9932 (16) | 0.5906 (6) | 0.0270 (14) | |
H3 | 0.4914 (7) | 0.9255 (15) | 0.5764 (6) | 0.0242 (13) | |
H4 | 0.3598 (9) | 0.7944 (17) | 0.5043 (5) | 0.0278 (14) | |
H5 | 0.3183 (9) | 0.8679 (18) | 0.7462 (6) | 0.0329 (16) | |
H6 | 0.5021 (9) | 0.8321 (18) | 0.7409 (6) | 0.0312 (16) | |
H7 | 0.3086 (10) | 0.415 (2) | 0.8029 (7) | 0.039 (2) | |
H8 | 0.6263 (11) | 0.462 (2) | 0.8153 (10) | 0.051 (3) | |
H9 | 0.5298 (15) | 0.257 (2) | 0.7400 (8) | 0.050 (2) | |
H10 | 0.5331 (15) | 0.205 (2) | 0.8584 (9) | 0.053 (3) | |
H11 | 0.4135 (16) | 0.522 (3) | 0.9619 (7) | 0.057 (3) | |
H12 | 0.5110 (13) | 0.764 (3) | 0.9155 (8) | 0.052 (2) | |
H13 | 0.3277 (15) | 0.789 (3) | 0.9125 (8) | 0.061 (3) | |
H14 | 0.0276 (8) | 0.3666 (17) | 0.3607 (5) | 0.0270 (14) | |
H15 | 0.1478 (8) | 0.8845 (16) | 0.3832 (6) | 0.0288 (14) | |
H16 | 0.0976 (9) | 0.7084 (18) | 0.4726 (5) | 0.0299 (15) | |
H17 | −0.0212 (8) | 0.789 (2) | 0.3860 (6) | 0.0327 (17) | |
H18 | 0.2009 (12) | 0.691 (2) | 0.2373 (7) | 0.046 (2) | |
H19 | 0.0159 (11) | 0.676 (2) | 0.2272 (7) | 0.0399 (19) | |
H20 | 0.1939 (13) | 0.210 (3) | 0.2082 (8) | 0.053 (3) | |
H21 | 0.1560 (18) | 0.264 (4) | 0.0377 (9) | 0.074 (3) | |
H22 | 0.2486 (19) | 0.529 (5) | 0.0869 (10) | 0.080 (4) | |
H23 | 0.0681 (19) | 0.559 (4) | 0.0553 (9) | 0.071 (3) | |
H24 | −0.0556 (17) | 0.133 (3) | 0.2401 (9) | 0.059 (3) | |
H25 | −0.0255 (18) | 0.044 (3) | 0.1283 (10) | 0.061 (3) | |
H26 | −0.1059 (14) | 0.326 (3) | 0.1469 (11) | 0.059 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0082 (11) | 0.0119 (13) | 0.0198 (13) | −0.0033 (12) | 0.0033 (10) | −0.0004 (11) |
O1 | 0.0096 (13) | 0.0179 (17) | 0.0231 (16) | 0.0009 (14) | 0.0027 (12) | 0.0020 (14) |
O2 | 0.0143 (15) | 0.0104 (15) | 0.034 (2) | −0.0057 (15) | 0.0027 (14) | −0.0005 (15) |
C2 | 0.0066 (11) | 0.0129 (13) | 0.0196 (13) | −0.0017 (11) | 0.0018 (9) | −0.0022 (10) |
N1 | 0.0102 (8) | 0.0141 (10) | 0.0187 (9) | −0.0033 (9) | 0.0014 (7) | −0.0002 (8) |
C3 | 0.0160 (13) | 0.0135 (14) | 0.0187 (13) | −0.0023 (12) | 0.0024 (10) | −0.0018 (11) |
C4 | 0.0190 (14) | 0.0212 (16) | 0.0224 (14) | −0.0033 (14) | 0.0011 (11) | 0.0046 (12) |
C5 | 0.0309 (18) | 0.0196 (17) | 0.0316 (19) | 0.0030 (17) | −0.0020 (14) | 0.0021 (15) |
C6 | 0.037 (2) | 0.041 (2) | 0.0183 (15) | 0.001 (2) | 0.0020 (14) | −0.0002 (16) |
C7 | 0.0096 (11) | 0.0148 (15) | 0.0195 (13) | 0.0032 (12) | 0.0001 (10) | −0.0012 (12) |
O3 | 0.0096 (13) | 0.0128 (15) | 0.0275 (17) | 0.0011 (14) | 0.0013 (12) | −0.0032 (13) |
O4 | 0.0159 (17) | 0.0130 (16) | 0.037 (2) | 0.0014 (15) | −0.0035 (15) | −0.0009 (16) |
C8 | 0.0097 (11) | 0.0166 (14) | 0.0189 (12) | 0.0000 (12) | 0.0010 (10) | 0.0018 (11) |
N2 | 0.0122 (9) | 0.0179 (11) | 0.0230 (10) | 0.0051 (10) | 0.0022 (8) | 0.0031 (9) |
C9 | 0.0199 (15) | 0.0242 (17) | 0.0186 (13) | −0.0016 (14) | 0.0015 (11) | 0.0045 (12) |
C10 | 0.0237 (16) | 0.041 (2) | 0.0202 (15) | 0.0021 (17) | 0.0038 (12) | −0.0019 (15) |
C11 | 0.039 (2) | 0.036 (2) | 0.035 (2) | −0.011 (2) | 0.0037 (17) | −0.003 (2) |
C12 | 0.055 (3) | 0.081 (4) | 0.0189 (17) | −0.021 (3) | 0.0078 (19) | −0.004 (2) |
H1 | 0.021 (3) | 0.020 (3) | 0.038 (3) | 0.002 (3) | 0.007 (2) | −0.003 (3) |
H2 | 0.026 (3) | 0.023 (3) | 0.033 (3) | 0.003 (3) | 0.007 (3) | 0.001 (3) |
H3 | 0.017 (2) | 0.021 (3) | 0.035 (3) | −0.005 (2) | 0.003 (2) | 0.002 (3) |
H4 | 0.030 (3) | 0.031 (4) | 0.022 (2) | −0.005 (3) | 0.000 (2) | −0.004 (2) |
H5 | 0.031 (3) | 0.029 (3) | 0.040 (4) | 0.007 (3) | 0.007 (3) | −0.002 (3) |
H6 | 0.029 (3) | 0.027 (4) | 0.037 (4) | −0.010 (3) | −0.002 (3) | −0.002 (3) |
H7 | 0.033 (3) | 0.037 (4) | 0.046 (4) | −0.014 (3) | −0.003 (3) | 0.011 (3) |
H8 | 0.032 (4) | 0.039 (5) | 0.080 (7) | 0.001 (3) | −0.005 (4) | 0.000 (4) |
H9 | 0.063 (6) | 0.037 (5) | 0.050 (4) | 0.007 (5) | −0.001 (4) | −0.008 (4) |
H10 | 0.065 (6) | 0.035 (4) | 0.057 (5) | 0.005 (4) | −0.003 (4) | 0.011 (4) |
H11 | 0.077 (7) | 0.063 (6) | 0.030 (4) | −0.001 (5) | 0.002 (4) | 0.011 (4) |
H12 | 0.053 (4) | 0.054 (5) | 0.048 (5) | −0.004 (4) | −0.004 (3) | −0.010 (4) |
H13 | 0.062 (5) | 0.077 (7) | 0.044 (5) | 0.022 (5) | 0.004 (4) | −0.007 (5) |
H14 | 0.022 (3) | 0.028 (3) | 0.032 (3) | −0.006 (3) | 0.004 (2) | 0.005 (3) |
H15 | 0.027 (3) | 0.024 (3) | 0.036 (3) | 0.005 (3) | 0.003 (3) | 0.004 (3) |
H16 | 0.030 (3) | 0.034 (4) | 0.026 (2) | 0.009 (3) | 0.002 (2) | 0.004 (2) |
H17 | 0.019 (2) | 0.045 (5) | 0.034 (3) | 0.014 (3) | 0.002 (2) | 0.006 (3) |
H18 | 0.047 (4) | 0.051 (5) | 0.039 (4) | −0.022 (4) | 0.004 (3) | 0.011 (4) |
H19 | 0.042 (4) | 0.041 (5) | 0.035 (4) | 0.008 (4) | −0.002 (3) | 0.004 (4) |
H20 | 0.051 (5) | 0.063 (6) | 0.044 (4) | 0.022 (5) | −0.002 (4) | −0.007 (4) |
H21 | 0.080 (8) | 0.101 (7) | 0.044 (5) | −0.016 (6) | 0.014 (5) | −0.019 (5) |
H22 | 0.071 (6) | 0.125 (10) | 0.045 (5) | −0.039 (6) | 0.021 (4) | −0.009 (6) |
H23 | 0.080 (6) | 0.096 (8) | 0.037 (5) | −0.010 (6) | 0.005 (4) | 0.007 (5) |
H24 | 0.069 (7) | 0.061 (6) | 0.048 (4) | −0.028 (6) | 0.007 (4) | −0.001 (4) |
H25 | 0.081 (8) | 0.047 (5) | 0.056 (5) | −0.011 (5) | 0.002 (5) | −0.012 (4) |
H26 | 0.046 (4) | 0.058 (5) | 0.072 (6) | −0.008 (4) | −0.010 (4) | −0.007 (5) |
Geometric parameters (Å, º) top
C1—O2 | 1.244 (5) | C7—O4 | 1.257 (6) |
C1—O1 | 1.257 (5) | C7—O3 | 1.263 (6) |
C1—C2 | 1.534 (4) | C7—C8 | 1.535 (5) |
C2—H1 | 1.099 (8) | C8—H14 | 1.096 (8) |
C2—N1 | 1.493 (4) | C8—N2 | 1.491 (5) |
C2—C3 | 1.540 (5) | C8—C9 | 1.530 (5) |
N1—H2 | 1.020 (8) | N2—H17 | 1.033 (8) |
N1—H4 | 1.046 (7) | N2—H15 | 1.041 (9) |
N1—H3 | 1.073 (7) | N2—H16 | 1.064 (8) |
C3—H5 | 1.101 (9) | C9—H18 | 1.082 (11) |
C3—H6 | 1.108 (8) | C9—H19 | 1.113 (11) |
C3—C4 | 1.527 (5) | C9—C10 | 1.536 (7) |
C4—H7 | 1.107 (9) | C10—H20 | 1.075 (13) |
C4—C5 | 1.526 (6) | C10—C12 | 1.519 (7) |
C4—C6 | 1.529 (6) | C10—C11 | 1.523 (7) |
C5—H9 | 1.078 (12) | C11—H25 | 1.073 (15) |
C5—H8 | 1.081 (12) | C11—H24 | 1.077 (14) |
C5—H10 | 1.098 (13) | C11—H26 | 1.079 (17) |
C6—H13 | 1.075 (15) | C12—H22 | 1.081 (18) |
C6—H12 | 1.079 (14) | C12—H23 | 1.11 (2) |
C6—H11 | 1.115 (13) | C12—H21 | 1.115 (19) |
| | | |
O2—C1—O1 | 124.9 (4) | O4—C7—O3 | 125.3 (4) |
O2—C1—C2 | 118.3 (3) | O4—C7—C8 | 117.7 (4) |
O1—C1—C2 | 116.8 (3) | O3—C7—C8 | 116.9 (3) |
H1—C2—N1 | 107.5 (5) | H14—C8—N2 | 107.6 (5) |
H1—C2—C1 | 110.2 (5) | H14—C8—C9 | 111.2 (5) |
N1—C2—C1 | 109.2 (3) | N2—C8—C9 | 108.2 (3) |
H1—C2—C3 | 110.9 (5) | H14—C8—C7 | 109.1 (5) |
N1—C2—C3 | 107.3 (3) | N2—C8—C7 | 109.5 (3) |
C1—C2—C3 | 111.6 (3) | C9—C8—C7 | 111.1 (3) |
H2—N1—H4 | 110.8 (7) | H17—N2—H15 | 109.7 (8) |
H2—N1—H3 | 108.6 (7) | H17—N2—H16 | 107.0 (7) |
H4—N1—H3 | 108.9 (7) | H15—N2—H16 | 107.3 (7) |
H2—N1—C2 | 110.9 (5) | H17—N2—C8 | 109.7 (6) |
H4—N1—C2 | 108.6 (5) | H15—N2—C8 | 112.0 (5) |
H3—N1—C2 | 109.2 (5) | H16—N2—C8 | 111.0 (6) |
H5—C3—H6 | 107.0 (8) | H18—C9—H19 | 107.1 (10) |
H5—C3—C4 | 109.5 (6) | H18—C9—C8 | 108.5 (6) |
H6—C3—C4 | 107.6 (5) | H19—C9—C8 | 106.9 (6) |
H5—C3—C2 | 108.7 (6) | H18—C9—C10 | 110.7 (8) |
H6—C3—C2 | 107.5 (5) | H19—C9—C10 | 107.8 (7) |
C4—C3—C2 | 116.1 (3) | C8—C9—C10 | 115.5 (4) |
H7—C4—C5 | 108.0 (7) | H20—C10—C12 | 110.5 (8) |
H7—C4—C3 | 109.3 (6) | H20—C10—C11 | 107.2 (9) |
C5—C4—C3 | 111.8 (3) | C12—C10—C11 | 110.5 (4) |
H7—C4—C6 | 109.1 (7) | H20—C10—C9 | 108.1 (8) |
C5—C4—C6 | 109.6 (3) | C12—C10—C9 | 109.8 (5) |
C3—C4—C6 | 109.0 (4) | C11—C10—C9 | 110.9 (4) |
H9—C5—H8 | 108.6 (12) | H25—C11—H24 | 107.6 (13) |
H9—C5—H10 | 106.2 (11) | H25—C11—H26 | 105.4 (13) |
H8—C5—H10 | 108.2 (11) | H24—C11—H26 | 107.3 (14) |
H9—C5—C4 | 112.2 (8) | H25—C11—C10 | 112.1 (10) |
H8—C5—C4 | 109.0 (7) | H24—C11—C10 | 114.5 (9) |
H10—C5—C4 | 112.5 (9) | H26—C11—C10 | 109.4 (9) |
H13—C6—H12 | 109.2 (13) | H22—C12—H23 | 107.0 (18) |
H13—C6—H11 | 107.1 (12) | H22—C12—H21 | 108.3 (15) |
H12—C6—H11 | 105.7 (11) | H23—C12—H21 | 108.3 (14) |
H13—C6—C4 | 113.2 (8) | H22—C12—C10 | 112.2 (9) |
H12—C6—C4 | 110.3 (7) | H23—C12—C10 | 110.8 (8) |
H11—C6—C4 | 111.1 (9) | H21—C12—C10 | 110.2 (11) |