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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616015699/fx5005sup1.cif
Contains datablocks leu_300, leu_120

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616015699/fx5005leu_300sup2.hkl
Contains datablock leu_300

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616015699/fx5005leu_120sup3.hkl
Contains datablock leu_120

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520616015699/fx5005leu_120sup4.cml
Supplementary material

CCDC references: 1508363; 1508364

Computing details top

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
C6H13NO2Z = 4
Mr = 131.17F(000) = 288
Monoclinic, P21Dx = 1.165 Mg m3
a = 9.606 (3) ÅNeutron radiation, λ = 0.80 Å
b = 5.324 (7) ŵ = 0.13 mm1
c = 14.666 (2) ÅT = 300 K
β = 94.06 (3)°Plate, colourless
V = 748.2 (10) Å32 × 0.5 × 0.2 mm
Data collection top
KOALA
diffractometer
Rint = 0.112
Laue scansθmax = 71.4°
24819 measured reflectionsh = 1919
1648 independent reflectionsk = 77
1367 reflections with I > 2σ(I)l = 1212
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll 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 = 1.10Δρmax = 0.55 e Å3
1647 reflectionsΔρmin = 0.63 e Å3
397 parametersAbsolute 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
xyzUiso*/Ueq
C10.2384 (3)0.4884 (7)0.6180 (2)0.0288 (7)
O10.1387 (4)0.6232 (9)0.5871 (3)0.0355 (10)
O20.2300 (5)0.2611 (10)0.6362 (4)0.0464 (12)
C20.3798 (3)0.6203 (7)0.6367 (2)0.0278 (7)
N10.3885 (3)0.8406 (5)0.57485 (18)0.0311 (6)
C30.3997 (4)0.7190 (9)0.7349 (3)0.0385 (9)
C40.4057 (5)0.5193 (12)0.8098 (3)0.0517 (11)
C50.5333 (7)0.3522 (14)0.8057 (5)0.0721 (16)
C60.4078 (11)0.658 (2)0.9035 (4)0.0843 (19)
C70.2532 (3)0.4009 (7)0.3867 (2)0.0279 (7)
O30.3469 (4)0.5525 (9)0.4141 (3)0.0352 (9)
O40.2665 (6)0.1690 (11)0.3817 (5)0.0525 (14)
C80.1136 (3)0.5157 (8)0.3521 (3)0.0324 (8)
N20.0874 (3)0.7497 (6)0.4056 (2)0.0391 (7)
C90.1115 (5)0.5906 (11)0.2518 (3)0.0508 (11)
C100.1137 (6)0.3740 (16)0.1839 (3)0.0677 (15)
C110.0254 (10)0.231 (2)0.1775 (6)0.091 (2)
C120.1427 (15)0.475 (3)0.0900 (5)0.122 (3)
H10.4627 (8)0.4897 (18)0.6210 (6)0.0464 (18)
H20.3220 (8)0.9803 (18)0.5910 (6)0.0451 (16)
H30.4915 (8)0.9138 (17)0.5793 (6)0.0432 (17)
H40.3639 (8)0.7819 (18)0.5076 (5)0.0465 (17)
H50.3177 (12)0.853 (2)0.7448 (7)0.065 (2)
H60.4982 (10)0.818 (2)0.7416 (6)0.057 (2)
H70.3127 (13)0.412 (3)0.8019 (8)0.080 (3)
H80.6254 (16)0.454 (3)0.8161 (13)0.097 (4)
H90.530 (2)0.256 (4)0.7459 (12)0.097 (4)
H100.535 (2)0.213 (4)0.8567 (13)0.106 (4)
H110.410 (2)0.528 (5)0.9577 (11)0.118 (5)
H120.496 (2)0.765 (4)0.9151 (11)0.108 (4)
H130.323 (2)0.771 (5)0.9099 (11)0.118 (5)
H140.0298 (8)0.387 (2)0.3641 (6)0.051 (2)
H150.1537 (9)0.8928 (19)0.3895 (7)0.0495 (18)
H160.1035 (9)0.7114 (19)0.4754 (6)0.0507 (18)
H170.0139 (9)0.813 (3)0.3940 (8)0.065 (3)
H180.1967 (14)0.718 (3)0.2437 (8)0.081 (3)
H190.0163 (13)0.705 (3)0.2369 (8)0.076 (3)
H200.1892 (18)0.241 (4)0.2079 (10)0.100 (4)
H210.147 (3)0.323 (6)0.0424 (13)0.155 (6)
H220.230 (3)0.584 (7)0.0922 (14)0.156 (7)
H230.059 (3)0.599 (7)0.0626 (15)0.151 (6)
H240.051 (3)0.162 (5)0.2422 (14)0.125 (5)
H250.026 (3)0.079 (5)0.1344 (14)0.123 (5)
H260.102 (2)0.341 (5)0.1548 (15)0.116 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0236 (14)0.0266 (18)0.0368 (17)0.0073 (13)0.0065 (12)0.0021 (14)
O10.0199 (16)0.038 (3)0.048 (2)0.0043 (16)0.0012 (15)0.002 (2)
O20.038 (2)0.032 (2)0.070 (3)0.0087 (19)0.003 (2)0.006 (2)
C20.0192 (14)0.0283 (18)0.0360 (16)0.0043 (13)0.0028 (11)0.0019 (13)
N10.0236 (11)0.0331 (15)0.0367 (13)0.0088 (11)0.0035 (9)0.0019 (11)
C30.0386 (18)0.041 (2)0.0350 (17)0.0038 (17)0.0005 (14)0.0038 (15)
C40.051 (2)0.065 (3)0.0386 (19)0.009 (2)0.0033 (16)0.0140 (19)
C50.073 (3)0.061 (3)0.079 (4)0.011 (3)0.016 (2)0.005 (3)
C60.100 (4)0.112 (5)0.040 (3)0.003 (4)0.005 (3)0.007 (3)
C70.0212 (13)0.0267 (18)0.0357 (17)0.0028 (12)0.0018 (12)0.0022 (13)
O30.0208 (16)0.034 (2)0.050 (2)0.0046 (15)0.0019 (15)0.0100 (18)
O40.039 (2)0.030 (2)0.089 (4)0.0050 (19)0.001 (2)0.006 (2)
C80.0200 (14)0.039 (2)0.0376 (16)0.0002 (14)0.0013 (11)0.0059 (15)
N20.0283 (13)0.0420 (18)0.0477 (16)0.0154 (13)0.0064 (11)0.0083 (13)
C90.051 (2)0.062 (3)0.0389 (19)0.011 (2)0.0053 (16)0.0121 (18)
C100.062 (3)0.097 (4)0.043 (2)0.011 (3)0.0022 (19)0.012 (3)
C110.092 (4)0.105 (5)0.075 (4)0.038 (4)0.005 (3)0.013 (4)
C120.149 (7)0.179 (8)0.039 (3)0.054 (7)0.020 (3)0.002 (4)
H10.030 (3)0.044 (4)0.065 (4)0.003 (3)0.004 (3)0.008 (4)
H20.039 (3)0.039 (4)0.058 (4)0.003 (3)0.008 (3)0.002 (3)
H30.034 (3)0.041 (4)0.055 (4)0.012 (3)0.004 (2)0.002 (3)
H40.043 (3)0.052 (4)0.045 (3)0.009 (3)0.003 (2)0.005 (3)
H50.072 (5)0.068 (6)0.055 (4)0.016 (4)0.009 (4)0.009 (4)
H60.060 (4)0.062 (6)0.049 (4)0.019 (4)0.004 (3)0.007 (4)
H70.077 (5)0.095 (7)0.068 (6)0.025 (5)0.011 (4)0.031 (5)
H80.072 (5)0.083 (7)0.135 (11)0.014 (5)0.002 (5)0.008 (7)
H90.116 (9)0.075 (8)0.098 (6)0.021 (7)0.012 (5)0.004 (5)
H100.119 (10)0.089 (7)0.107 (7)0.013 (6)0.017 (6)0.022 (7)
H110.148 (12)0.141 (9)0.064 (6)0.003 (8)0.004 (6)0.007 (6)
H120.120 (7)0.126 (10)0.076 (8)0.008 (7)0.006 (5)0.019 (7)
H130.126 (7)0.156 (11)0.071 (8)0.024 (8)0.003 (6)0.009 (7)
H140.033 (3)0.062 (5)0.059 (4)0.007 (3)0.001 (3)0.012 (4)
H150.047 (4)0.039 (4)0.062 (5)0.006 (3)0.007 (3)0.004 (3)
H160.049 (4)0.050 (5)0.054 (4)0.011 (4)0.010 (3)0.007 (3)
H170.038 (3)0.080 (6)0.076 (5)0.025 (4)0.008 (3)0.024 (5)
H180.083 (5)0.100 (8)0.059 (5)0.041 (6)0.001 (4)0.018 (5)
H190.074 (5)0.091 (8)0.062 (5)0.009 (5)0.010 (4)0.013 (5)
H200.103 (7)0.124 (8)0.072 (6)0.015 (7)0.001 (5)0.018 (6)
H210.190 (16)0.207 (12)0.068 (7)0.047 (10)0.019 (8)0.019 (8)
H220.176 (9)0.221 (15)0.075 (9)0.075 (11)0.029 (7)0.008 (9)
H230.180 (10)0.197 (13)0.075 (9)0.043 (10)0.003 (8)0.013 (9)
H240.144 (12)0.136 (12)0.096 (6)0.046 (10)0.017 (6)0.005 (7)
H250.149 (12)0.121 (8)0.099 (8)0.037 (7)0.003 (8)0.023 (7)
H260.095 (6)0.127 (8)0.123 (11)0.037 (6)0.011 (6)0.014 (7)
Geometric parameters (Å, º) top
C1—O21.243 (7)C7—O41.244 (7)
C1—O11.256 (6)C7—O31.254 (6)
C1—C21.536 (4)C7—C81.527 (5)
C2—H11.094 (9)C8—H141.082 (9)
C2—N11.489 (5)C8—N21.503 (6)
C2—C31.532 (5)C8—C91.524 (6)
N1—H21.019 (10)N2—H151.032 (11)
N1—H41.045 (8)N2—H171.033 (8)
N1—H31.061 (7)N2—H161.044 (10)
C3—H51.079 (12)C9—H181.077 (13)
C3—H61.081 (10)C9—H191.108 (15)
C3—C41.527 (7)C9—C101.524 (9)
C4—H71.059 (14)C10—H201.05 (2)
C4—C51.520 (9)C10—C121.522 (10)
C4—C61.558 (9)C10—C111.537 (10)
C5—H91.01 (2)C11—H260.98 (4)
C5—H81.04 (2)C11—H251.02 (3)
C5—H101.05 (2)C11—H241.06 (3)
C6—H131.02 (3)C12—H221.02 (4)
C6—H121.03 (3)C12—H211.07 (3)
C6—H111.05 (2)C12—H231.09 (5)
O2—C1—O1125.0 (4)O4—C7—O3125.7 (5)
O2—C1—C2118.5 (4)O4—C7—C8118.0 (4)
O1—C1—C2116.4 (4)O3—C7—C8116.2 (4)
H1—C2—N1107.4 (6)H14—C8—N2106.7 (6)
H1—C2—C3111.8 (6)H14—C8—C9111.3 (6)
N1—C2—C3107.1 (3)N2—C8—C9107.2 (4)
H1—C2—C1108.6 (6)H14—C8—C7109.8 (6)
N1—C2—C1109.8 (3)N2—C8—C7109.5 (3)
C3—C2—C1112.0 (3)C9—C8—C7112.1 (3)
H2—N1—H4109.5 (8)H15—N2—H17108.1 (9)
H2—N1—H3108.4 (8)H15—N2—H16108.5 (8)
H4—N1—H3108.4 (7)H17—N2—H16107.4 (8)
H2—N1—C2111.7 (5)H15—N2—C8111.3 (6)
H4—N1—C2108.7 (6)H17—N2—C8112.0 (8)
H3—N1—C2110.2 (5)H16—N2—C8109.3 (6)
H5—C3—H6107.9 (10)H18—C9—H19104.7 (13)
H5—C3—C4110.6 (7)H18—C9—C8108.3 (7)
H6—C3—C4106.7 (7)H19—C9—C8106.8 (8)
H5—C3—C2108.0 (7)H18—C9—C10111.1 (10)
H6—C3—C2107.6 (6)H19—C9—C10109.7 (9)
C4—C3—C2115.7 (4)C8—C9—C10115.6 (5)
H7—C4—C5110.9 (11)H20—C10—C12111.9 (12)
H7—C4—C3107.9 (7)H20—C10—C9109.3 (10)
C5—C4—C3111.6 (5)C12—C10—C9109.7 (8)
H7—C4—C6108.0 (9)H20—C10—C11105.2 (13)
C5—C4—C6110.6 (5)C12—C10—C11109.4 (7)
C3—C4—C6107.6 (6)C9—C10—C11111.3 (6)
H9—C5—H8111.1 (17)H26—C11—H25106.7 (19)
H9—C5—H10104.9 (17)H26—C11—H24107 (2)
H8—C5—H10107.1 (15)H25—C11—H24107 (2)
H9—C5—C4110.9 (11)H26—C11—C10110.7 (14)
H8—C5—C4111.7 (11)H25—C11—C10113.6 (15)
H10—C5—C4110.9 (13)H24—C11—C10111.6 (14)
H13—C6—H12108 (2)H22—C12—H21113 (2)
H13—C6—H11106.9 (19)H22—C12—H23104 (3)
H12—C6—H11105.7 (17)H21—C12—H23106 (2)
H13—C6—C4113.6 (11)H22—C12—C10112.0 (14)
H12—C6—C4111.6 (11)H21—C12—C10110.0 (17)
H11—C6—C4110.7 (14)H23—C12—C10111.6 (14)
(leu_120) 2-amino-4-methylpentanoic acid top
Crystal data top
C6H13NO2Z = 4
Mr = 131.17F(000) = 288
Monoclinic, P21Dx = 1.187 Mg m3
a = 9.562 (2) ÅNeutron radiation, λ = 0.80 Å
b = 5.301 (1) ŵ = 0.0 mm1
c = 14.519 (3) ÅT = 120 K
β = 94.20 (2)°Plate, colourless
V = 734.0 (3) Å32 × 0.5 × 0.2 mm
Data collection top
KOALA
diffractometer
Rint = 0.156
Laue scansθmax = 71.4°
21729 measured reflectionsh = 1414
2430 independent reflectionsk = 78
1955 reflections with I > 2σ(I)l = 2222
Refinement top
Refinement on F2361 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079All 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 reflectionsΔρmax = 1.29 e Å3
397 parametersΔρmin = 1.40 e Å3
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
xyzUiso*/Ueq
C10.2364 (3)0.5018 (7)0.6168 (2)0.0132 (6)
O10.1364 (4)0.6377 (9)0.5851 (3)0.0168 (7)
O20.2267 (4)0.2744 (8)0.6365 (3)0.0196 (8)
C20.3793 (3)0.6312 (7)0.6347 (2)0.0130 (6)
N10.3863 (2)0.8535 (5)0.57206 (16)0.0143 (4)
C30.4010 (4)0.7295 (7)0.7346 (2)0.0160 (6)
C40.4055 (4)0.5299 (8)0.8106 (3)0.0209 (7)
C50.5306 (5)0.3530 (9)0.8055 (3)0.0276 (8)
C60.4135 (5)0.6616 (11)0.9045 (3)0.0321 (9)
C70.2524 (3)0.3905 (7)0.3862 (2)0.0147 (6)
O30.3463 (4)0.5453 (8)0.4147 (3)0.0166 (7)
O40.2674 (5)0.1553 (9)0.3824 (3)0.0222 (8)
C80.1113 (3)0.5015 (7)0.3487 (2)0.0150 (6)
N20.0823 (3)0.7371 (5)0.39997 (18)0.0177 (5)
C90.1130 (4)0.5668 (8)0.2461 (3)0.0209 (7)
C100.1156 (4)0.3402 (11)0.1804 (3)0.0281 (8)
C110.0243 (6)0.2017 (11)0.1749 (4)0.0367 (11)
C120.1500 (7)0.4288 (16)0.0852 (3)0.0513 (16)
H10.4639 (8)0.5013 (16)0.6190 (6)0.0262 (13)
H20.3205 (8)0.9932 (16)0.5906 (6)0.0270 (14)
H30.4914 (7)0.9255 (15)0.5764 (6)0.0242 (13)
H40.3598 (9)0.7944 (17)0.5043 (5)0.0278 (14)
H50.3183 (9)0.8679 (18)0.7462 (6)0.0329 (16)
H60.5021 (9)0.8321 (18)0.7409 (6)0.0312 (16)
H70.3086 (10)0.415 (2)0.8029 (7)0.039 (2)
H80.6263 (11)0.462 (2)0.8153 (10)0.051 (3)
H90.5298 (15)0.257 (2)0.7400 (8)0.050 (2)
H100.5331 (15)0.205 (2)0.8584 (9)0.053 (3)
H110.4135 (16)0.522 (3)0.9619 (7)0.057 (3)
H120.5110 (13)0.764 (3)0.9155 (8)0.052 (2)
H130.3277 (15)0.789 (3)0.9125 (8)0.061 (3)
H140.0276 (8)0.3666 (17)0.3607 (5)0.0270 (14)
H150.1478 (8)0.8845 (16)0.3832 (6)0.0288 (14)
H160.0976 (9)0.7084 (18)0.4726 (5)0.0299 (15)
H170.0212 (8)0.789 (2)0.3860 (6)0.0327 (17)
H180.2009 (12)0.691 (2)0.2373 (7)0.046 (2)
H190.0159 (11)0.676 (2)0.2272 (7)0.0399 (19)
H200.1939 (13)0.210 (3)0.2082 (8)0.053 (3)
H210.1560 (18)0.264 (4)0.0377 (9)0.074 (3)
H220.2486 (19)0.529 (5)0.0869 (10)0.080 (4)
H230.0681 (19)0.559 (4)0.0553 (9)0.071 (3)
H240.0556 (17)0.133 (3)0.2401 (9)0.059 (3)
H250.0255 (18)0.044 (3)0.1283 (10)0.061 (3)
H260.1059 (14)0.326 (3)0.1469 (11)0.059 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0082 (11)0.0119 (13)0.0198 (13)0.0033 (12)0.0033 (10)0.0004 (11)
O10.0096 (13)0.0179 (17)0.0231 (16)0.0009 (14)0.0027 (12)0.0020 (14)
O20.0143 (15)0.0104 (15)0.034 (2)0.0057 (15)0.0027 (14)0.0005 (15)
C20.0066 (11)0.0129 (13)0.0196 (13)0.0017 (11)0.0018 (9)0.0022 (10)
N10.0102 (8)0.0141 (10)0.0187 (9)0.0033 (9)0.0014 (7)0.0002 (8)
C30.0160 (13)0.0135 (14)0.0187 (13)0.0023 (12)0.0024 (10)0.0018 (11)
C40.0190 (14)0.0212 (16)0.0224 (14)0.0033 (14)0.0011 (11)0.0046 (12)
C50.0309 (18)0.0196 (17)0.0316 (19)0.0030 (17)0.0020 (14)0.0021 (15)
C60.037 (2)0.041 (2)0.0183 (15)0.001 (2)0.0020 (14)0.0002 (16)
C70.0096 (11)0.0148 (15)0.0195 (13)0.0032 (12)0.0001 (10)0.0012 (12)
O30.0096 (13)0.0128 (15)0.0275 (17)0.0011 (14)0.0013 (12)0.0032 (13)
O40.0159 (17)0.0130 (16)0.037 (2)0.0014 (15)0.0035 (15)0.0009 (16)
C80.0097 (11)0.0166 (14)0.0189 (12)0.0000 (12)0.0010 (10)0.0018 (11)
N20.0122 (9)0.0179 (11)0.0230 (10)0.0051 (10)0.0022 (8)0.0031 (9)
C90.0199 (15)0.0242 (17)0.0186 (13)0.0016 (14)0.0015 (11)0.0045 (12)
C100.0237 (16)0.041 (2)0.0202 (15)0.0021 (17)0.0038 (12)0.0019 (15)
C110.039 (2)0.036 (2)0.035 (2)0.011 (2)0.0037 (17)0.003 (2)
C120.055 (3)0.081 (4)0.0189 (17)0.021 (3)0.0078 (19)0.004 (2)
H10.021 (3)0.020 (3)0.038 (3)0.002 (3)0.007 (2)0.003 (3)
H20.026 (3)0.023 (3)0.033 (3)0.003 (3)0.007 (3)0.001 (3)
H30.017 (2)0.021 (3)0.035 (3)0.005 (2)0.003 (2)0.002 (3)
H40.030 (3)0.031 (4)0.022 (2)0.005 (3)0.000 (2)0.004 (2)
H50.031 (3)0.029 (3)0.040 (4)0.007 (3)0.007 (3)0.002 (3)
H60.029 (3)0.027 (4)0.037 (4)0.010 (3)0.002 (3)0.002 (3)
H70.033 (3)0.037 (4)0.046 (4)0.014 (3)0.003 (3)0.011 (3)
H80.032 (4)0.039 (5)0.080 (7)0.001 (3)0.005 (4)0.000 (4)
H90.063 (6)0.037 (5)0.050 (4)0.007 (5)0.001 (4)0.008 (4)
H100.065 (6)0.035 (4)0.057 (5)0.005 (4)0.003 (4)0.011 (4)
H110.077 (7)0.063 (6)0.030 (4)0.001 (5)0.002 (4)0.011 (4)
H120.053 (4)0.054 (5)0.048 (5)0.004 (4)0.004 (3)0.010 (4)
H130.062 (5)0.077 (7)0.044 (5)0.022 (5)0.004 (4)0.007 (5)
H140.022 (3)0.028 (3)0.032 (3)0.006 (3)0.004 (2)0.005 (3)
H150.027 (3)0.024 (3)0.036 (3)0.005 (3)0.003 (3)0.004 (3)
H160.030 (3)0.034 (4)0.026 (2)0.009 (3)0.002 (2)0.004 (2)
H170.019 (2)0.045 (5)0.034 (3)0.014 (3)0.002 (2)0.006 (3)
H180.047 (4)0.051 (5)0.039 (4)0.022 (4)0.004 (3)0.011 (4)
H190.042 (4)0.041 (5)0.035 (4)0.008 (4)0.002 (3)0.004 (4)
H200.051 (5)0.063 (6)0.044 (4)0.022 (5)0.002 (4)0.007 (4)
H210.080 (8)0.101 (7)0.044 (5)0.016 (6)0.014 (5)0.019 (5)
H220.071 (6)0.125 (10)0.045 (5)0.039 (6)0.021 (4)0.009 (6)
H230.080 (6)0.096 (8)0.037 (5)0.010 (6)0.005 (4)0.007 (5)
H240.069 (7)0.061 (6)0.048 (4)0.028 (6)0.007 (4)0.001 (4)
H250.081 (8)0.047 (5)0.056 (5)0.011 (5)0.002 (5)0.012 (4)
H260.046 (4)0.058 (5)0.072 (6)0.008 (4)0.010 (4)0.007 (5)
Geometric parameters (Å, º) top
C1—O21.244 (5)C7—O41.257 (6)
C1—O11.257 (5)C7—O31.263 (6)
C1—C21.534 (4)C7—C81.535 (5)
C2—H11.099 (8)C8—H141.096 (8)
C2—N11.493 (4)C8—N21.491 (5)
C2—C31.540 (5)C8—C91.530 (5)
N1—H21.020 (8)N2—H171.033 (8)
N1—H41.046 (7)N2—H151.041 (9)
N1—H31.073 (7)N2—H161.064 (8)
C3—H51.101 (9)C9—H181.082 (11)
C3—H61.108 (8)C9—H191.113 (11)
C3—C41.527 (5)C9—C101.536 (7)
C4—H71.107 (9)C10—H201.075 (13)
C4—C51.526 (6)C10—C121.519 (7)
C4—C61.529 (6)C10—C111.523 (7)
C5—H91.078 (12)C11—H251.073 (15)
C5—H81.081 (12)C11—H241.077 (14)
C5—H101.098 (13)C11—H261.079 (17)
C6—H131.075 (15)C12—H221.081 (18)
C6—H121.079 (14)C12—H231.11 (2)
C6—H111.115 (13)C12—H211.115 (19)
O2—C1—O1124.9 (4)O4—C7—O3125.3 (4)
O2—C1—C2118.3 (3)O4—C7—C8117.7 (4)
O1—C1—C2116.8 (3)O3—C7—C8116.9 (3)
H1—C2—N1107.5 (5)H14—C8—N2107.6 (5)
H1—C2—C1110.2 (5)H14—C8—C9111.2 (5)
N1—C2—C1109.2 (3)N2—C8—C9108.2 (3)
H1—C2—C3110.9 (5)H14—C8—C7109.1 (5)
N1—C2—C3107.3 (3)N2—C8—C7109.5 (3)
C1—C2—C3111.6 (3)C9—C8—C7111.1 (3)
H2—N1—H4110.8 (7)H17—N2—H15109.7 (8)
H2—N1—H3108.6 (7)H17—N2—H16107.0 (7)
H4—N1—H3108.9 (7)H15—N2—H16107.3 (7)
H2—N1—C2110.9 (5)H17—N2—C8109.7 (6)
H4—N1—C2108.6 (5)H15—N2—C8112.0 (5)
H3—N1—C2109.2 (5)H16—N2—C8111.0 (6)
H5—C3—H6107.0 (8)H18—C9—H19107.1 (10)
H5—C3—C4109.5 (6)H18—C9—C8108.5 (6)
H6—C3—C4107.6 (5)H19—C9—C8106.9 (6)
H5—C3—C2108.7 (6)H18—C9—C10110.7 (8)
H6—C3—C2107.5 (5)H19—C9—C10107.8 (7)
C4—C3—C2116.1 (3)C8—C9—C10115.5 (4)
H7—C4—C5108.0 (7)H20—C10—C12110.5 (8)
H7—C4—C3109.3 (6)H20—C10—C11107.2 (9)
C5—C4—C3111.8 (3)C12—C10—C11110.5 (4)
H7—C4—C6109.1 (7)H20—C10—C9108.1 (8)
C5—C4—C6109.6 (3)C12—C10—C9109.8 (5)
C3—C4—C6109.0 (4)C11—C10—C9110.9 (4)
H9—C5—H8108.6 (12)H25—C11—H24107.6 (13)
H9—C5—H10106.2 (11)H25—C11—H26105.4 (13)
H8—C5—H10108.2 (11)H24—C11—H26107.3 (14)
H9—C5—C4112.2 (8)H25—C11—C10112.1 (10)
H8—C5—C4109.0 (7)H24—C11—C10114.5 (9)
H10—C5—C4112.5 (9)H26—C11—C10109.4 (9)
H13—C6—H12109.2 (13)H22—C12—H23107.0 (18)
H13—C6—H11107.1 (12)H22—C12—H21108.3 (15)
H12—C6—H11105.7 (11)H23—C12—H21108.3 (14)
H13—C6—C4113.2 (8)H22—C12—C10112.2 (9)
H12—C6—C4110.3 (7)H23—C12—C10110.8 (8)
H11—C6—C4111.1 (9)H21—C12—C10110.2 (11)
 

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