A reinvestigation of the crystal structure of the 1:1 mixture of the two racemates DL-isoleucine and DL-allo-isoleucine, with a detailed analysis of interatomic distances between alternative side-chain positions, reveals a systematic distribution of the four stereoisomers in this crystal. Two different molecular chains exist in the crystal and each such chain accommodates a single diastereomeric pair only (L-isoleucine:D-allo-isoleucine or D-isoleucine:L-allo-isoleucine). The crystal is built up by a stacking of such chains in two dimensions and three different packing modes for the two types of chains are discussed. Crystallization experiments of the two individual racemates in the 1:1 mixture of DL-isoleucine:DL-allo-isoleucine have been undertaken. The structure of the racemate DL-isoleucine is presented. The molecular arrangements in this racemate and the 1:1 DL-isoleucine:DL-allo-isoleucine mixture are closely related. Furthermore, the spontaneous resolution of enantiomers upon crystallization of the other racemate, DL-allo-isoleucine, is rationalized on the basis of the aforementioned analysis of interatomic distances in the 1:1 DL-isoleucine:DL-allo-isoleucine complex. Structural data for a new L-isoleucine: D-allo-isoleucine complex are also given.
Supporting information
CCDC references: 148921; 148922; 148923; 148924
For all compounds, program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: SHELXTL (Sheldrick, 1995).
Crystal data top
C6H13NO2 | Z = 2 |
Mr = 131.17 | F(000) = 144 |
Triclinic, P1 | Dx = 1.255 Mg m−3 |
a = 5.2289 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 5.4102 (1) Å | Cell parameters from 4333 reflections |
c = 13.1095 (3) Å | µ = 0.09 mm−1 |
α = 96.332 (1)° | T = 150 K |
β = 90.622 (1)° | Plate, colourless |
γ = 109.493 (1)° | 0.50 × 0.50 × 0.10 mm |
V = 347.02 (1) Å3 | |
Data collection top
Siemens SMART CCD diffractometer | 5815 independent reflections |
Radiation source: fine-focus sealed tube | 4439 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 40°, θmin = 3.1° |
Absorption correction: multi-scan (sheldrick, 1996) | h = −10→9 |
Tmin = 0.955, Tmax = 0.991 | k = −9→11 |
8317 measured reflections | l = −26→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters not defined? |
S = 1.06 | Calculated w = 1/[σ2(Fo2) + (0.0888P)2 + 0.025P] where P = (Fo2 + 2Fc2)/3 |
5815 reflections | (Δ/σ)max = 0.001 |
101 parameters | Δρmax = 0.62 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
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 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
etc. and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.80323 (9) | 0.75963 (8) | 0.58960 (4) | 0.01627 (9) | |
O2 | 0.36212 (9) | 0.63846 (9) | 0.62394 (4) | 0.01616 (9) | |
N1 | 0.81846 (10) | 0.26922 (9) | 0.57840 (4) | 0.01351 (8) | |
H1 | 0.988 (3) | 0.389 (3) | 0.6066 (10) | 0.023 (3)* | |
H2 | 0.812 (3) | 0.114 (3) | 0.5854 (10) | 0.024 (3)* | |
H3 | 0.803 (3) | 0.282 (3) | 0.5104 (10) | 0.023 (3)* | |
C1 | 0.58380 (11) | 0.59662 (10) | 0.61346 (4) | 0.01216 (8) | |
C2 | 0.58889 (10) | 0.32193 (10) | 0.63253 (4) | 0.01191 (8) | |
H4 | 0.422 (2) | 0.1918 (16) | 0.6033 (4) | 0.014* | |
C3 | 0.61101 (12) | 0.29197 (11) | 0.74779 (5) | 0.01447 (9) | |
H5 | 0.6824 (9) | 0.1440 (18) | 0.75333 (8) | 0.017* | |
C4 | 0.81181 (15) | 0.54061 (14) | 0.80856 (6) | 0.02060 (12) | |
H6 | 0.9808 (15) | 0.6004 (11) | 0.7712 (5) | 0.031* | |
H7 | 0.8542 (14) | 0.5001 (6) | 0.8772 (6) | 0.031* | |
H8 | 0.730 (1) | 0.6817 (13) | 0.8165 (6) | 0.031* | |
C5 | 0.33004 (15) | 0.2148 (2) | 0.79270 (6) | 0.02330 (13) | |
H9 | 0.2639 (7) | 0.3641 (15) | 0.79461 (6) | 0.028* | |
H10 | 0.2044 (12) | 0.0679 (14) | 0.7474 (4) | 0.028* | |
C6 | 0.3293 (2) | 0.1342 (2) | 0.90085 (7) | 0.0371 (2) | |
H11 | 0.1417 (19) | 0.077 (2) | 0.9240 (4) | 0.056* | |
H12 | 0.444 (2) | 0.2862 (17) | 0.9484 (5) | 0.056* | |
H13 | 0.402 (2) | −0.013 (2) | 0.9001 (2) | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0163 (2) | 0.01012 (14) | 0.0230 (2) | 0.00421 (11) | 0.00542 (14) | 0.00458 (13) |
O2 | 0.0145 (2) | 0.0146 (2) | 0.0208 (2) | 0.00693 (12) | 0.00167 (13) | 0.00182 (14) |
N1 | 0.0159 (2) | 0.01003 (15) | 0.0154 (2) | 0.00513 (12) | 0.00445 (14) | 0.00233 (13) |
C1 | 0.0145 (2) | 0.0095 (2) | 0.0126 (2) | 0.00435 (13) | 0.00142 (14) | 0.00099 (13) |
C2 | 0.0131 (2) | 0.0091 (2) | 0.0135 (2) | 0.00361 (12) | 0.00200 (14) | 0.00155 (13) |
C3 | 0.0173 (2) | 0.0129 (2) | 0.0138 (2) | 0.00547 (15) | 0.0027 (2) | 0.00282 (15) |
C4 | 0.0230 (3) | 0.0190 (2) | 0.0170 (3) | 0.0045 (2) | −0.0016 (2) | −0.0006 (2) |
C5 | 0.0218 (3) | 0.0258 (3) | 0.0221 (3) | 0.0059 (2) | 0.0093 (2) | 0.0078 (2) |
C6 | 0.0444 (5) | 0.0363 (4) | 0.0186 (3) | −0.0033 (4) | 0.0103 (3) | 0.0066 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.2592 (7) | C3—H5 | 0.999 (12) |
O2—C1 | 1.2591 (7) | C4—H6 | 0.989 (8) |
N1—C2 | 1.4927 (7) | C4—H7 | 0.989 (8) |
N1—H1 | 0.948 (13) | C4—H8 | 0.989 (8) |
N1—H2 | 0.845 (14) | C5—C6 | 1.5282 (12) |
N1—H3 | 0.906 (13) | C5—H9 | 0.977 (10) |
C1—C2 | 1.5427 (7) | C5—H10 | 0.977 (10) |
C2—C3 | 1.5445 (8) | C6—H11 | 0.987 (10) |
C2—H4 | 0.963 (12) | C6—H12 | 0.987 (10) |
C3—C5 | 1.5307 (9) | C6—H13 | 0.987 (10) |
C3—C4 | 1.5328 (9) | | |
| | | |
C2—N1—H1 | 110.9 (8) | C2—C3—H5 | 107.43 (3) |
C2—N1—H2 | 108.7 (9) | C3—C4—H6 | 109.47 (4) |
H1—N1—H2 | 108.8 (11) | C3—C4—H7 | 109.47 (4) |
C2—N1—H3 | 110.2 (8) | H6—C4—H7 | 109.5 |
H1—N1—H3 | 109.6 (11) | C3—C4—H8 | 109.47 (4) |
H2—N1—H3 | 108.5 (12) | H6—C4—H8 | 109.5 |
O1—C1—O2 | 125.92 (5) | H7—C4—H8 | 109.5 |
O1—C1—C2 | 116.80 (5) | C6—C5—C3 | 113.28 (7) |
O2—C1—C2 | 117.28 (5) | C6—C5—H9 | 108.92 (6) |
N1—C2—C1 | 109.39 (4) | C3—C5—H9 | 108.92 (4) |
N1—C2—C3 | 110.18 (5) | C6—C5—H10 | 108.92 (5) |
C1—C2—C3 | 113.02 (4) | C3—C5—H10 | 108.92 (4) |
N1—C2—H4 | 108.03 (3) | H9—C5—H10 | 107.7 |
C1—C2—H4 | 108.03 (3) | C5—C6—H11 | 109.47 (5) |
C3—C2—H4 | 108.03 (3) | C5—C6—H12 | 109.47 (5) |
C5—C3—C4 | 111.87 (6) | H11—C6—H12 | 109.5 |
C5—C3—C2 | 110.49 (5) | C5—C6—H13 | 109.47 (6) |
C4—C3—C2 | 111.92 (5) | H11—C6—H13 | 109.5 |
C5—C3—H5 | 107.43 (4) | H12—C6—H13 | 109.5 |
C4—C3—H5 | 107.43 (4) | | |
| | | |
O1—C1—C2—N1 | −22.95 (7) | N1—C2—C3—C4 | 81.48 (6) |
O2—C1—C2—N1 | 157.62 (5) | N1—C2—C3—C5 | −153.14 (5) |
O1—C1—C2—C3 | 100.20 (6) | C1—C2—C3—C4 | −41.24 (6) |
O2—C1—C2—C3 | −79.22 (6) | C4—C3—C5—C6 | −64.80 (9) |
C1—C2—C3—C5 | 84.14 (6) | C2—C3—C5—C6 | 169.79 (7) |
Crystal data top
C6H13NO2 | V = 351.42 (2) Å3 |
Mr = 131.17 | Z = 2 |
Triclinic, P1 | F(000) = 144 |
Hall symbol: P 1 | Dx = 1.240 Mg m−3 |
a = 5.2438 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 5.3978 (2) Å | Cell parameters from 3483 reflections |
c = 13.2562 (6) Å | µ = 0.09 mm−1 |
α = 93.042 (1)° | T = 140 K |
β = 92.811 (1)° | Plate, colourless |
γ = 109.897 (1)° | 0.45 × 0.25 × 0.10 mm |
Data collection top
Siemens SMART CCD diffractometer | 4029 independent reflections |
Radiation source: fine-focus sealed tube | 3746 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.010 |
ω scans | θmax = 32.5°, θmin = 1.5° |
Absorption correction: multi-scan (sheldrick, 1996) | h = −8→5 |
Tmin = 0.959, Tmax = 0.991 | k = −8→9 |
4788 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters not defined? |
wR(F2) = 0.097 | Calculated w = 1/[σ2(Fo2) + (0.0675P)2 + 0.0025P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
4028 reflections | Δρmax = 0.44 e Å−3 |
201 parameters | Δρmin = −0.22 e Å−3 |
3 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.14 (64) |
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 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
etc. and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.9524 (2) | 0.6557 (2) | 0.57652 (6) | 0.0149 (2) | |
O2A | 0.5127 (2) | 0.5281 (2) | 0.61114 (6) | 0.01442 (15) | |
N1A | 0.9645 (2) | 0.1650 (2) | 0.56582 (7) | 0.0118 (2) | |
H1A | 1.163 (7) | 0.282 (7) | 0.597 (2) | 0.063 (8)* | |
H2A | 0.963 (5) | −0.003 (5) | 0.5731 (16) | 0.033 (6)* | |
H3A | 0.940 (5) | 0.177 (4) | 0.5070 (16) | 0.026 (5)* | |
C1A | 0.7340 (2) | 0.4885 (2) | 0.60067 (7) | 0.0105 (2) | |
C2A | 0.7406 (2) | 0.2121 (2) | 0.62044 (7) | 0.0105 (2) | |
H4A | 0.574 (3) | 0.086 (3) | 0.5937 (5) | 0.013* | |
C3A | 0.7765 (2) | 0.1732 (2) | 0.73401 (7) | 0.0124 (2) | |
H5A | 0.8479 (15) | 0.025 (3) | 0.73930 (13) | 0.015* | |
C4A | 0.9848 (3) | 0.4177 (3) | 0.79132 (9) | 0.0184 (2) | |
H6A | 1.145 (2) | 0.4767 (15) | 0.7546 (6) | 0.028* | |
H7A | 1.0310 (18) | 0.3740 (8) | 0.8573 (9) | 0.028* | |
H8A | 0.9087 (12) | 0.5555 (19) | 0.7979 (7) | 0.028* | |
C5A | 0.5015 (3) | 0.0912 (3) | 0.78135 (9) | 0.0203 (2) | |
H9A | 0.4383 (10) | 0.238 (2) | 0.78416 (10) | 0.024* | |
H10A | 0.373 (2) | −0.048 (2) | 0.7389 (7) | 0.024* | |
C6A | 0.5155 (3) | −0.0009 (3) | 0.88809 (9) | 0.0303 (2) | |
H11A | 0.327 (3) | −0.067 (3) | 0.9129 (6) | 0.045* | |
H12A | 0.635 (3) | 0.152 (2) | 0.9351 (7) | 0.045* | |
H13A | 0.593 (3) | −0.148 (3) | 0.8865 (2) | 0.045* | |
O1B | 0.3355 (2) | 0.15514 (15) | 0.40100 (6) | 0.01413 (15) | |
O2B | 0.7748 (2) | 0.2815 (2) | 0.36717 (6) | 0.0144 (2) | |
N1B | 0.3217 (2) | 0.6441 (2) | 0.41060 (7) | 0.0117 (2) | |
H1B | 0.173 (3) | 0.536 (3) | 0.3866 (10) | 0.003 (3)* | |
H2B | 0.327 (4) | 0.810 (4) | 0.4049 (13) | 0.018 (4)* | |
H3B | 0.339 (4) | 0.620 (3) | 0.4793 (13) | 0.013 (4)* | |
C1B | 0.5541 (2) | 0.3217 (2) | 0.37729 (7) | 0.0108 (2) | |
C2B | 0.5494 (2) | 0.5993 (2) | 0.35807 (7) | 0.0109 (2) | |
H4B | 0.715 (3) | 0.726 (3) | 0.3867 (6) | 0.013* | |
C3B | 0.5233 (2) | 0.6409 (2) | 0.24385 (8) | 0.0141 (2) | |
H5B | 0.4450 (16) | 0.798 (3) | 0.2368 (2) | 0.017* | |
C4B | 0.8033 (3) | 0.7279 (3) | 0.20184 (11) | 0.0264 (3) | |
H6B | 0.9269 (19) | 0.884 (3) | 0.2435 (8) | 0.040* | |
H7B | 0.7876 (6) | 0.774 (3) | 0.131 (1) | 0.040* | |
H8B | 0.8773 (16) | 0.582 (2) | 0.2037 (9) | 0.040* | |
C5B | 0.3228 (3) | 0.3951 (3) | 0.18385 (8) | 0.0187 (2) | |
H9B | 0.3994 (11) | 0.249 (2) | 0.18493 (8) | 0.022* | |
H10B | 0.149 (2) | 0.3370 (8) | 0.2182 (5) | 0.022* | |
C6B | 0.2612 (3) | 0.4403 (3) | 0.07347 (8) | 0.0318 (3) | |
H11B | 0.120 (3) | 0.290 (2) | 0.0433 (5) | 0.048* | |
H12B | 0.419 (2) | 0.468 (3) | 0.0376 (6) | 0.048* | |
H13B | 0.207 (3) | 0.590 (3) | 0.07145 (11) | 0.048* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0139 (4) | 0.0090 (3) | 0.0224 (4) | 0.0041 (3) | 0.0039 (3) | 0.0037 (3) |
O2A | 0.0122 (3) | 0.0130 (4) | 0.0206 (3) | 0.0077 (3) | 0.0006 (3) | 0.0023 (3) |
N1A | 0.0122 (4) | 0.0089 (4) | 0.0152 (3) | 0.0045 (3) | 0.0026 (3) | 0.0019 (3) |
C1A | 0.0109 (4) | 0.0085 (4) | 0.0128 (3) | 0.0044 (3) | −0.0001 (3) | 0.0007 (3) |
C2A | 0.0102 (4) | 0.0079 (4) | 0.0139 (4) | 0.0037 (3) | 0.0007 (3) | 0.0015 (3) |
C3A | 0.0127 (4) | 0.0110 (4) | 0.0144 (4) | 0.0048 (4) | 0.0015 (3) | 0.0031 (3) |
C4A | 0.0182 (5) | 0.0181 (5) | 0.0170 (4) | 0.0046 (4) | −0.0029 (3) | 0.0002 (4) |
C5A | 0.0165 (5) | 0.0228 (6) | 0.0214 (4) | 0.0049 (4) | 0.0064 (4) | 0.0072 (4) |
C6A | 0.0335 (6) | 0.0328 (6) | 0.0208 (4) | 0.0044 (5) | 0.0097 (4) | 0.0084 (4) |
O1B | 0.0132 (3) | 0.0085 (3) | 0.0220 (3) | 0.0047 (3) | 0.0039 (3) | 0.0038 (3) |
O2B | 0.0111 (3) | 0.0138 (4) | 0.0197 (3) | 0.0063 (3) | −0.0003 (3) | 0.0006 (3) |
N1B | 0.0131 (4) | 0.0082 (4) | 0.0152 (3) | 0.0051 (3) | 0.0022 (3) | 0.0020 (3) |
C1B | 0.0122 (4) | 0.0086 (4) | 0.0122 (3) | 0.0049 (3) | −0.0008 (3) | 0.0007 (3) |
C2B | 0.0100 (4) | 0.0082 (4) | 0.0152 (4) | 0.0038 (3) | 0.0011 (3) | 0.0020 (3) |
C3B | 0.0160 (5) | 0.0125 (5) | 0.0161 (4) | 0.0069 (4) | 0.0042 (3) | 0.0050 (3) |
C4B | 0.0220 (6) | 0.0297 (8) | 0.0285 (6) | 0.0072 (5) | 0.0131 (5) | 0.0112 (5) |
C5B | 0.0221 (5) | 0.0188 (6) | 0.0142 (4) | 0.0062 (4) | −0.0010 (4) | 0.0008 (4) |
C6B | 0.0401 (7) | 0.0430 (7) | 0.0151 (4) | 0.0183 (6) | −0.0020 (4) | 0.0030 (4) |
Geometric parameters (Å, º) top
O1A—C1A | 1.2619 (12) | O1B—C1B | 1.2589 (13) |
O2A—C1A | 1.2622 (13) | O2B—C1B | 1.2602 (13) |
N1A—C2A | 1.4950 (15) | N1B—C2B | 1.4932 (15) |
N1A—H1A | 1.06 (4) | N1B—H1B | 0.84 (2) |
N1A—H2A | 0.92 (3) | N1B—H2B | 0.89 (2) |
N1A—H3A | 0.79 (2) | N1B—H3B | 0.93 (2) |
C1A—C2A | 1.5397 (15) | C1B—C2B | 1.542 (2) |
C2A—C3A | 1.5425 (13) | C2B—C3B | 1.5486 (14) |
C2A—H4A | 0.94 (2) | C2B—H4B | 0.95 (2) |
C3A—C4A | 1.531 (2) | C3B—C4B | 1.525 (2) |
C3A—C5A | 1.534 (2) | C3B—C5B | 1.535 (2) |
C3A—H5A | 1.00 (2) | C3B—H5B | 1.06 (2) |
C4A—H6A | 0.959 (12) | C4B—H6B | 0.990 (14) |
C4A—H7A | 0.959 (12) | C4B—H7B | 0.990 (13) |
C4A—H8A | 0.959 (12) | C4B—H8B | 0.990 (13) |
C5A—C6A | 1.531 (2) | C5B—C6B | 1.533 (2) |
C5A—H9A | 0.955 (14) | C5B—H9B | 1.000 (14) |
C5A—H10A | 0.955 (15) | C5B—H10B | 1.000 (14) |
C6A—H11A | 1.008 (14) | C6B—H11B | 0.946 (14) |
C6A—H12A | 1.008 (14) | C6B—H12B | 0.946 (14) |
C6A—H13A | 1.008 (14) | C6B—H13B | 0.946 (14) |
| | | |
C2A—N1A—H1A | 113.7 (16) | C2B—N1B—H1B | 110.2 (10) |
C2A—N1A—H2A | 110.2 (15) | C2B—N1B—H2B | 109.8 (12) |
H1A—N1A—H2A | 103 (3) | H1B—N1B—H2B | 111.1 (16) |
C2A—N1A—H3A | 109.5 (17) | C2B—N1B—H3B | 110.0 (12) |
H1A—N1A—H3A | 114 (2) | H1B—N1B—H3B | 107.8 (14) |
H2A—N1A—H3A | 107 (2) | H2B—N1B—H3B | 107.9 (16) |
O1A—C1A—O2A | 126.02 (10) | O1B—C1B—O2B | 126.01 (10) |
O1A—C1A—C2A | 116.67 (9) | O1B—C1B—C2B | 116.74 (9) |
O2A—C1A—C2A | 117.30 (8) | O2B—C1B—C2B | 117.25 (9) |
N1A—C2A—C1A | 109.32 (8) | N1B—C2B—C1B | 109.26 (8) |
N1A—C2A—C3A | 109.85 (8) | N1B—C2B—C3B | 110.43 (9) |
C1A—C2A—C3A | 113.05 (8) | C1B—C2B—C3B | 112.60 (8) |
N1A—C2A—H4A | 108.16 (6) | N1B—C2B—H4B | 108.14 (6) |
C1A—C2A—H4A | 108.16 (5) | C1B—C2B—H4B | 108.14 (5) |
C3A—C2A—H4A | 108.16 (5) | C3B—C2B—H4B | 108.14 (6) |
C4A—C3A—C5A | 111.91 (10) | C4B—C3B—C5B | 112.18 (11) |
C4A—C3A—C2A | 111.90 (8) | C4B—C3B—C2B | 109.99 (10) |
C5A—C3A—C2A | 110.65 (9) | C5B—C3B—C2B | 111.94 (8) |
C4A—C3A—H5A | 107.37 (7) | C4B—C3B—H5B | 107.50 (8) |
C5A—C3A—H5A | 107.37 (7) | C5B—C3B—H5B | 107.50 (7) |
C2A—C3A—H5A | 107.37 (5) | C2B—C3B—H5B | 107.50 (6) |
C3A—C4A—H6A | 109.47 (6) | C3B—C4B—H6B | 109.47 (8) |
C3A—C4A—H7A | 109.47 (6) | C3B—C4B—H7B | 109.47 (7) |
H6A—C4A—H7A | 109.5 | H6B—C4B—H7B | 109.5 |
C3A—C4A—H8A | 109.47 (7) | C3B—C4B—H8B | 109.47 (8) |
H6A—C4A—H8A | 109.5 | H6B—C4B—H8B | 109.5 |
H7A—C4A—H8A | 109.5 | H7B—C4B—H8B | 109.5 |
C6A—C5A—C3A | 112.96 (11) | C6B—C5B—C3B | 113.56 (11) |
C6A—C5A—H9A | 108.99 (8) | C6B—C5B—H9B | 108.86 (8) |
C3A—C5A—H9A | 108.99 (7) | C3B—C5B—H9B | 108.86 (7) |
C6A—C5A—H10A | 108.99 (7) | C6B—C5B—H10B | 108.86 (8) |
C3A—C5A—H10A | 108.99 (7) | C3B—C5B—H10B | 108.86 (6) |
H9A—C5A—H10A | 107.8 | H9B—C5B—H10B | 107.7 |
C5A—C6A—H11A | 109.47 (7) | C5B—C6B—H11B | 109.47 (7) |
C5A—C6A—H12A | 109.47 (7) | C5B—C6B—H12B | 109.47 (8) |
H11A—C6A—H12A | 109.5 | H11B—C6B—H12B | 109.5 |
C5A—C6A—H13A | 109.47 (8) | C5B—C6B—H13B | 109.47 (8) |
H11A—C6A—H13A | 109.5 | H11B—C6B—H13B | 109.5 |
H12A—C6A—H13A | 109.5 | H12B—C6B—H13B | 109.5 |
| | | |
O1A—C1A—C2A—N1A | −23.81 (12) | O1B—C1B—C2B—N1B | 22.43 (12) |
O2A—C1A—C2A—N1A | 156.97 (8) | O2B—C1B—C2B—N1B | −158.08 (8) |
O1A—C1A—C2A—C3A | 98.89 (10) | O1B—C1B—C2B—C3B | −100.66 (11) |
O2A—C1A—C2A—C3A | −80.33 (11) | O2B—C1B—C2B—C3B | 78.83 (11) |
N1A—C2A—C3A—C4A | 81.08 (11) | N1B—C2B—C3B—C4B | 152.52 (11) |
C1A—C2A—C3A—C4A | −41.33 (13) | C1B—C2B—C3B—C4B | −85.04 (12) |
N1A—C2A—C3A—C5A | −153.38 (10) | N1B—C2B—C3B—C5B | −82.05 (12) |
C1A—C2A—C3A—C5A | 84.21 (11) | C1B—C2B—C3B—C5B | 40.38 (13) |
C4A—C3A—C5A—C6A | −65.37 (15) | C4B—C3B—C5B—C6B | −63.7 (2) |
C2A—C3A—C5A—C6A | 169.1 (1) | C2B—C3B—C5B—C6B | 172.06 (10) |
Crystal data top
C6H13NO2 | Z = 2 |
Mr = 131.17 | F(000) = 144 |
Triclinic, P1 | Dx = 1.235 Mg m−3 |
a = 5.2493 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 5.4006 (1) Å | Cell parameters from 6724 reflections |
c = 13.2778 (2) Å | µ = 0.09 mm−1 |
α = 92.9433 (6)° | T = 150 K |
β = 92.8659 (5)° | Plate, colourless |
γ = 109.8571 (7)° | 0.75 × 0.55 × 0.30 mm |
V = 352.66 (1) Å3 | |
Data collection top
Siemens SMART CCD diffractometer | 6187 independent reflections |
Radiation source: fine-focus sealed tube | 5540 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 40.0°, θmin = 3.1° |
Absorption correction: multi-scan (sheldrick, 1996) | h = −10→10 |
Tmin = 0.933, Tmax = 0.973 | k = −10→10 |
9079 measured reflections | l = −28→28 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H-atom parameters not defined? |
wR(F2) = 0.194 | Calculated w = 1/[σ2(Fo2) + (0.0561P)2 + 0.1597P] where P = (Fo2 + 2Fc2)/3 |
S = 1.25 | (Δ/σ)max = 0.032 |
6187 reflections | Δρmax = 0.59 e Å−3 |
116 parameters | Δρmin = −0.34 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 1.23 (7) |
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 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
etc. and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.30806 (12) | 0.75015 (11) | 0.58772 (5) | 0.01528 (10) | |
O2 | −0.13094 (12) | 0.62306 (12) | 0.62196 (5) | 0.01533 (10) | |
N1 | 0.32122 (13) | 0.26020 (12) | 0.57762 (5) | 0.01253 (10) | |
H1 | 0.490 (5) | 0.363 (5) | 0.6040 (18) | 0.034 (5)* | |
H2 | 0.328 (4) | 0.098 (4) | 0.5816 (15) | 0.021 (4)* | |
H3 | 0.288 (5) | 0.280 (5) | 0.5182 (18) | 0.031 (5)* | |
C1 | 0.08990 (14) | 0.58294 (13) | 0.61158 (5) | 0.01132 (10) | |
C2 | 0.09599 (13) | 0.30626 (13) | 0.63118 (5) | 0.01136 (10) | |
H4 | −0.056 (3) | 0.191 (2) | 0.6059 (5) | 0.014* | |
C3 | 0.1269 (2) | 0.26586 (15) | 0.74491 (6) | 0.01437 (11) | |
H5 | 0.2041 (13) | 0.109 (3) | 0.75126 (12) | 0.017* | |
C4 | 0.3310 (2) | 0.5107 (2) | 0.80368 (7) | 0.02080 (15) | 0.50 |
H6 | 0.476 (5) | 0.580 (4) | 0.7665 (14) | 0.031* | 0.50 |
H7 | 0.388 (4) | 0.4641 (17) | 0.863 (2) | 0.031* | 0.50 |
H8 | 0.250 (3) | 0.633 (4) | 0.8160 (18) | 0.031* | 0.50 |
C5 | −0.1495 (2) | 0.1817 (2) | 0.78999 (9) | 0.0256 (2) | 0.50 |
H9 | −0.290 (6) | 0.024 (6) | 0.7432 (18) | 0.031* | 0.50 |
H10 | −0.223 (3) | 0.342 (6) | 0.79204 (12) | 0.031* | 0.50 |
C6 | −0.1310 (6) | 0.0921 (6) | 0.8984 (2) | 0.0337 (5) | 0.50 |
H11 | −0.316 (6) | 0.031 (7) | 0.9246 (13) | 0.051* | 0.50 |
H12 | −0.007 (7) | 0.244 (5) | 0.9437 (16) | 0.051* | 0.50 |
H13 | −0.058 (7) | −0.056 (7) | 0.8969 (4) | 0.051* | 0.50 |
C4' | −0.1495 (2) | 0.1817 (2) | 0.78999 (9) | 0.0256 (2) | 0.50 |
H6' | −0.262 (6) | 0.037 (4) | 0.755 (3) | 0.038* | 0.50 |
H7' | −0.219 (2) | 0.312 (8) | 0.787 (3) | 0.038* | 0.50 |
H8' | −0.130 (4) | 0.148 (6) | 0.855 (3) | 0.038* | 0.50 |
C5' | 0.3310 (2) | 0.5107 (2) | 0.80368 (7) | 0.02080 (15) | 0.50 |
H9' | 0.2601 (6) | 0.661 (3) | 0.8007 (7) | 0.025* | 0.50 |
H10' | 0.507 (5) | 0.5621 (12) | 0.7704 (9) | 0.025* | 0.50 |
C6' | 0.3840 (7) | 0.4649 (7) | 0.9153 (2) | 0.0344 (5) | 0.50 |
H11' | 0.535 (7) | 0.603 (6) | 0.9439 (12) | 0.052* | 0.50 |
H12' | 0.416 (7) | 0.306 (6) | 0.9190 (3) | 0.052* | 0.50 |
H13' | 0.233 (6) | 0.458 (7) | 0.9505 (13) | 0.052* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0151 (2) | 0.0096 (2) | 0.0221 (2) | 0.00470 (14) | 0.0046 (2) | 0.00406 (15) |
O2 | 0.0128 (2) | 0.0146 (2) | 0.0206 (2) | 0.0074 (2) | 0.0003 (2) | 0.0016 (2) |
N1 | 0.0143 (2) | 0.0096 (2) | 0.0149 (2) | 0.00525 (15) | 0.0030 (2) | 0.00215 (14) |
C1 | 0.0122 (2) | 0.0096 (2) | 0.0130 (2) | 0.0050 (2) | 0.0000 (2) | 0.00119 (15) |
C2 | 0.0112 (2) | 0.0089 (2) | 0.0143 (2) | 0.00371 (15) | 0.0011 (2) | 0.00182 (15) |
C3 | 0.0166 (3) | 0.0131 (2) | 0.0149 (2) | 0.0064 (2) | 0.0030 (2) | 0.0043 (2) |
C4 | 0.0238 (4) | 0.0207 (3) | 0.0160 (3) | 0.0059 (3) | −0.0025 (2) | 0.0005 (2) |
C5 | 0.0220 (4) | 0.0288 (4) | 0.0265 (4) | 0.0069 (3) | 0.0111 (3) | 0.0101 (3) |
C6 | 0.0377 (12) | 0.0378 (12) | 0.0213 (8) | 0.0049 (9) | 0.0111 (8) | 0.0101 (8) |
C4' | 0.0220 (4) | 0.0288 (4) | 0.0265 (4) | 0.0069 (3) | 0.0111 (3) | 0.0101 (3) |
C5' | 0.0238 (4) | 0.0207 (3) | 0.0160 (3) | 0.0059 (3) | −0.0025 (2) | 0.0005 (2) |
C6' | 0.0441 (14) | 0.0478 (15) | 0.0149 (7) | 0.0208 (12) | −0.0014 (8) | 0.0033 (8) |
Geometric parameters (Å, º) top
O1—C1 | 1.2611 (9) | C3—C4' | 1.5289 (13) |
O2—C1 | 1.2623 (9) | C3—C5' | 1.5338 (12) |
N1—C2 | 1.4937 (9) | C5—H9 | 1.06 (4) |
N1—H1 | 0.91 (2) | C5—H10 | 1.06 (4) |
N1—H2 | 0.89 (2) | C6—H11 | 1.00 (3) |
N1—H3 | 0.82 (2) | C6—H12 | 1.00 (3) |
C1—C2 | 1.5404 (9) | C6—H13 | 1.00 (3) |
C2—C3 | 1.5453 (10) | C4'—H6' | 0.89 (2) |
C2—H4 | 0.87 (2) | C4'—H7' | 0.89 (5) |
C3—C4 | 1.5338 (12) | C4'—H8' | 0.89 (3) |
C3—C5 | 1.5289 (13) | C5'—C6' | 1.542 (2) |
C3—H5 | 1.06 (2) | C5'—H9' | 1.002 (13) |
C4—H6 | 0.91 (3) | C5'—H10' | 1.00 (3) |
C4—H7 | 0.91 (3) | C6'—H11' | 0.93 (3) |
C4—H8 | 0.91 (3) | C6'—H12' | 0.93 (3) |
C5—C6 | 1.551 (3) | C6'—H13' | 0.93 (3) |
| | | |
C2—N1—H1 | 113.6 (15) | C3—C5—C6 | 111.44 (14) |
C2—N1—H2 | 114.0 (13) | C3—C5—H9 | 109.34 (6) |
H1—N1—H2 | 102.2 (19) | C6—C5—H9 | 109.34 (13) |
C2—N1—H3 | 104.5 (16) | C3—C5—H10 | 109.34 (5) |
H1—N1—H3 | 115 (2) | C6—C5—H10 | 109.34 (13) |
H2—N1—H3 | 108 (2) | H9—C5—H10 | 108.0 |
O1—C1—O2 | 125.90 (6) | C5—C6—H11 | 109.47 (12) |
O1—C1—C2 | 116.75 (6) | C5—C6—H12 | 109.47 (13) |
O2—C1—C2 | 117.34 (6) | H11—C6—H12 | 109.5 |
N1—C2—C1 | 109.33 (5) | C5—C6—H13 | 109.47 (13) |
N1—C2—C3 | 110.23 (6) | H11—C6—H13 | 109.47 (6) |
C1—C2—C3 | 112.82 (6) | H12—C6—H13 | 109.5 |
N1—C2—H4 | 108.11 (4) | C3—C4'—H6' | 109.4 (12) |
C1—C2—H4 | 108.11 (4) | C3—C4'—H7' | 109.5 (12) |
C3—C2—H4 | 108.11 (4) | H6'—C4'—H7' | 109.5 (19) |
C4'—C3—C5' | 111.76 (8) | C3—C4'—H8' | 109.5 (9) |
C5—C3—C4 | 111.76 (8) | H6'—C4'—H8' | 110 (2) |
C4'—C3—C2 | 110.60 (7) | H7'—C4'—H8' | 109 (2) |
C5—C3—C2 | 110.60 (7) | C3—C5'—C6' | 112.67 (15) |
C5'—C3—C2 | 112.04 (6) | C3—C5'—H9' | 109.0 (5) |
C4—C3—C2 | 112.04 (6) | C6'—C5'—H9' | 109.0 (6) |
C5—C3—H5 | 107.39 (5) | C3—C5'—H10' | 109.0 (4) |
C4—C3—H5 | 107.39 (5) | C6'—C5'—H10' | 109.0 (5) |
C2—C3—H5 | 107.39 (4) | H9'—C5'—H10' | 107.9 (4) |
C3—C4—H6 | 109.47 (5) | C5'—C6'—H11' | 109.47 (14) |
C3—C4—H7 | 109.47 (5) | C5'—C6'—H12' | 109.47 (12) |
H6—C4—H7 | 109.5 | H11'—C6'—H12' | 109.5 |
C3—C4—H8 | 109.47 (5) | C5'—C6'—H13' | 109.47 (13) |
H6—C4—H8 | 109.5 | H11'—C6'—H13' | 109.5 |
H7—C4—H8 | 109.5 | H12'—C6'—H13' | 109.47 (5) |
| | | |
O1—C1—C2—N1 | −23.30 (9) | C4'—C3—C5—C6 | 0.100 |
O2—C1—C2—N1 | 157.53 (6) | C5'—C3—C5—C6 | −64.5 (2) |
O1—C1—C2—C3 | 99.75 (8) | C4—C3—C5—C6 | −64.5 (2) |
O2—C1—C2—C3 | −79.42 (8) | C2—C3—C5—C6 | 169.89 (15) |
C1—C2—C3—C4' | 84.51 (8) | N1—C2—C3—C4' | −152.95 (7) |
N1—C2—C3—C5 | −152.95 (7) | N1—C2—C3—C5' | 81.64 (8) |
C1—C2—C3—C5 | 84.51 (8) | C4'—C3—C5'—C6' | 60.5 (2) |
C1—C2—C3—C5' | −40.90 (9) | C5—C3—C5'—C6' | 60.5 (2) |
N1—C2—C3—C4 | 81.64 (8) | C4—C3—C5'—C6' | 0.94 |
C1—C2—C3—C4 | −40.90 (9) | C2—C3—C5'—C6' | −174.73 (14) |
Crystal data top
C6H13NO2 | F(000) = 288 |
Mr = 131.17 | Dx = 1.227 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6706 (1) Å | Cell parameters from 7959 reflections |
b = 5.2583 (1) Å | µ = 0.09 mm−1 |
c = 14.1018 (2) Å | T = 150 K |
β = 98.033 (1)° | Plate, colourless |
V = 710.05 (2) Å3 | 0.90 × 0.50 × 0.05 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD diffractometer | 11372 independent reflections |
Radiation source: fine-focus sealed tube | 8967 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 40.0°, θmin = 1.5° |
Absorption correction: multi-scan (sheldrick, 1996) | h = −16→20 |
Tmin = 0.921, Tmax = 0.995 | k = −10→10 |
16583 measured reflections | l = −30→25 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters not defined? |
wR(F2) = 0.124 | Calculated w = 1/[σ2(Fo2) + (0.0567P)2 + 0.0061P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = −0.002 |
11371 reflections | Δρmax = 0.54 e Å−3 |
196 parameters | Δρmin = −0.31 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.63 (41) |
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 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
etc. and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.64390 (5) | 0.61873 (11) | 0.58600 (4) | 0.01513 (8) | |
O2A | 0.73315 (5) | 0.99335 (10) | 0.63843 (4) | 0.01703 (9) | |
N1A | 0.89125 (6) | 0.40288 (11) | 0.57706 (4) | 0.01317 (8) | |
H1A | 0.8415 (14) | 0.289 (3) | 0.6025 (10) | 0.026 (3)* | |
H2A | 0.9777 (14) | 0.344 (3) | 0.5773 (9) | 0.022 (3)* | |
H3A | 0.8598 (14) | 0.438 (3) | 0.5172 (10) | 0.028 (3)* | |
C1A | 0.74430 (6) | 0.76242 (12) | 0.61626 (4) | 0.01199 (9) | |
C2A | 0.89164 (6) | 0.64770 (12) | 0.63091 (5) | 0.01219 (9) | |
H4A | 0.9554 (8) | 0.7683 (15) | 0.6038 (3) | 0.015* | |
C3A | 0.94808 (6) | 0.60705 (13) | 0.73830 (5) | 0.01464 (10) | |
H5A | 1.0226 (10) | 0.4781 (17) | 0.74185 (7) | 0.018* | |
C4A | 1.01413 (9) | 0.8529 (2) | 0.78089 (7) | 0.0249 (2) | |
H6A | 1.0824 (10) | 0.9165 (11) | 0.7401 (5) | 0.037* | |
H7A | 1.0626 (9) | 0.8194 (5) | 0.8465 (7) | 0.037* | |
H8A | 0.9403 (7) | 0.9825 (13) | 0.7837 (6) | 0.037* | |
C5A | 0.83562 (8) | 0.5049 (2) | 0.79516 (5) | 0.01878 (11) | |
H9A | 0.7623 (7) | 0.6316 (12) | 0.79429 (5) | 0.023* | |
H10A | 0.7943 (4) | 0.3534 (15) | 0.7635 (3) | 0.023* | |
C6A | 0.89085 (12) | 0.4393 (2) | 0.89933 (6) | 0.0304 (2) | |
H11A | 0.8170 (8) | 0.351 (2) | 0.9288 (4) | 0.046* | |
H12A | 0.9178 (11) | 0.5978 (16) | 0.9353 (4) | 0.046* | |
H13A | 0.9735 (11) | 0.327 (2) | 0.90132 (8) | 0.046* | |
O1B | 1.16317 (5) | 1.22830 (11) | 0.58923 (4) | 0.01637 (9) | |
O2B | 1.24741 (6) | 1.62364 (11) | 0.61395 (4) | 0.02034 (10) | |
N1B | 1.43383 (6) | 1.04848 (12) | 0.60816 (4) | 0.01535 (9) | |
H1B | 1.3871 (16) | 0.917 (3) | 0.6197 (11) | 0.028 (3)* | |
H2B | 1.5251 (14) | 1.013 (3) | 0.6248 (10) | 0.024 (3)* | |
H3B | 1.4143 (13) | 1.084 (3) | 0.5462 (10) | 0.020 (3)* | |
C1B | 1.25852 (6) | 1.38685 (12) | 0.61819 (5) | 0.01262 (9) | |
C2B | 1.39799 (6) | 1.27240 (13) | 0.66580 (5) | 0.01338 (9) | |
H4B | 1.4691 (10) | 1.3963 (17) | 0.66696 (5) | 0.016* | |
C3B | 1.38807 (7) | 1.18566 (14) | 0.76921 (5) | 0.01600 (11) | |
H5B | 1.313 (1) | 1.0596 (17) | 0.76637 (6) | 0.019* | |
C4B | 1.52314 (9) | 1.0579 (2) | 0.81456 (7) | 0.0289 (2) | |
H6B | 1.5448 (6) | 0.9100 (19) | 0.7736 (6) | 0.043* | |
H7B | 1.5117 (4) | 0.9947 (19) | 0.8805 (7) | 0.043* | |
H8B | 1.6021 (8) | 1.1845 (14) | 0.8195 (7) | 0.043* | |
C5B | 1.34993 (10) | 1.4083 (2) | 0.83059 (6) | 0.0320 (2) | |
H9B | 1.42612 (13) | 1.5228 (2) | 0.84033 (6) | 0.038* | |
H10B | 1.27286 (11) | 1.4962 (2) | 0.79688 (9) | 0.038* | |
C6B | 1.31314 (10) | 1.3257 (2) | 0.92814 (7) | 0.0469 (3) | |
H11B | 1.28998 (10) | 1.4777 (2) | 0.9645 (1) | 0.070* | |
H12B | 1.39405 (11) | 1.2363 (2) | 0.9645 (1) | 0.070* | |
H13B | 1.23156 (13) | 1.2095 (2) | 0.91861 (6) | 0.070* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.01018 (15) | 0.0166 (2) | 0.0186 (2) | −0.00049 (15) | 0.00182 (14) | −0.0012 (2) |
O2A | 0.0145 (2) | 0.0113 (2) | 0.0254 (2) | 0.00250 (15) | 0.0033 (2) | −0.0008 (2) |
N1A | 0.0111 (2) | 0.0130 (2) | 0.0156 (2) | 0.00231 (15) | 0.0023 (2) | −0.0012 (2) |
C1A | 0.0099 (2) | 0.0121 (2) | 0.0143 (2) | 0.0016 (2) | 0.0028 (2) | 0.0009 (2) |
C2A | 0.0091 (2) | 0.0110 (2) | 0.0167 (2) | 0.0007 (2) | 0.0024 (2) | −0.0008 (2) |
C3A | 0.0122 (2) | 0.0142 (2) | 0.0168 (2) | 0.0012 (2) | −0.0002 (2) | −0.0017 (2) |
C4A | 0.0231 (3) | 0.0208 (3) | 0.0285 (4) | −0.0044 (2) | −0.0050 (3) | −0.0056 (3) |
C5A | 0.0197 (3) | 0.0213 (3) | 0.0153 (2) | −0.0002 (2) | 0.0026 (2) | 0.0004 (2) |
C6A | 0.0397 (5) | 0.0357 (5) | 0.0152 (3) | 0.0002 (4) | 0.0016 (3) | 0.0009 (3) |
O1B | 0.0103 (2) | 0.0156 (2) | 0.0226 (2) | 0.00147 (14) | 0.00016 (15) | −0.0042 (2) |
O2B | 0.0189 (2) | 0.0119 (2) | 0.0295 (3) | 0.0034 (2) | 0.0010 (2) | 0.0020 (2) |
N1B | 0.0127 (2) | 0.0169 (2) | 0.0167 (2) | 0.0054 (2) | 0.0029 (2) | 0.0018 (2) |
C1B | 0.0107 (2) | 0.0120 (2) | 0.0151 (2) | 0.0018 (2) | 0.0016 (2) | 0.0000 (2) |
C2B | 0.0097 (2) | 0.0139 (2) | 0.0163 (2) | 0.0006 (2) | 0.0014 (2) | 0.0009 (2) |
C3B | 0.0125 (2) | 0.0200 (3) | 0.0152 (2) | −0.0011 (2) | 0.0010 (2) | 0.0011 (2) |
C4B | 0.0201 (3) | 0.0423 (5) | 0.0237 (3) | 0.0078 (3) | 0.0015 (3) | 0.0132 (3) |
C5B | 0.0406 (5) | 0.0346 (5) | 0.0201 (3) | 0.0087 (4) | 0.0019 (3) | −0.0065 (3) |
C6B | 0.0505 (6) | 0.0718 (10) | 0.0192 (4) | 0.0068 (7) | 0.0075 (4) | −0.0104 (5) |
Geometric parameters (Å, º) top
O1A—C1A | 1.2569 (8) | O1B—C1B | 1.2676 (8) |
O2A—C1A | 1.2623 (8) | O2B—C1B | 1.2504 (9) |
N1A—C2A | 1.4944 (8) | N1B—C2B | 1.4986 (9) |
N1A—H1A | 0.876 (15) | N1B—H1B | 0.85 (2) |
N1A—H2A | 0.891 (14) | N1B—H2B | 0.901 (14) |
N1A—H3A | 0.876 (15) | N1B—H3B | 0.888 (13) |
C1A—C2A | 1.5344 (8) | C1B—C2B | 1.5424 (8) |
C2A—C3A | 1.5512 (9) | C2B—C3B | 1.5437 (9) |
C2A—H4A | 0.997 (12) | C2B—H4B | 0.946 (13) |
C3A—C4A | 1.5271 (11) | C3B—C4B | 1.5275 (11) |
C3A—C5A | 1.5356 (10) | C3B—C5B | 1.5316 (11) |
C3A—H5A | 0.986 (13) | C3B—H5B | 0.980 (13) |
C4A—H6A | 0.992 (9) | C4B—H6B | 1.008 (10) |
C4A—H7A | 0.992 (9) | C4B—H7B | 1.008 (10) |
C4A—H8A | 0.992 (9) | C4B—H8B | 1.008 (10) |
C5A—C6A | 1.5306 (11) | C5B—C6B | 1.5312 (14) |
C5A—H9A | 0.972 (9) | C5B—H9B | 0.95 |
C5A—H10A | 0.972 (9) | C5B—H10B | 0.95 |
C6A—H11A | 0.991 (10) | C6B—H11B | 0.99 |
C6A—H12A | 0.991 (10) | C6B—H12B | 0.99 |
C6A—H13A | 0.991 (10) | C6B—H13B | 0.99 |
| | | |
C2A—N1A—H1A | 110.2 (10) | C2B—N1B—H1B | 111.4 (10) |
C2A—N1A—H2A | 111.1 (9) | C2B—N1B—H2B | 108.2 (10) |
H1A—N1A—H2A | 109.3 (13) | H1B—N1B—H2B | 108.1 (14) |
C2A—N1A—H3A | 106.6 (11) | C2B—N1B—H3B | 109.6 (9) |
H1A—N1A—H3A | 113.6 (13) | H1B—N1B—H3B | 108.2 (13) |
H2A—N1A—H3A | 106.0 (12) | H2B—N1B—H3B | 111.4 (12) |
O1A—C1A—O2A | 125.00 (6) | O2B—C1B—O1B | 125.86 (6) |
O1A—C1A—C2A | 117.91 (6) | O2B—C1B—C2B | 118.25 (6) |
O2A—C1A—C2A | 117.05 (5) | O1B—C1B—C2B | 115.85 (6) |
N1A—C2A—C1A | 109.51 (5) | N1B—C2B—C1B | 108.96 (5) |
N1A—C2A—C3A | 110.67 (5) | N1B—C2B—C3B | 109.26 (6) |
C1A—C2A—C3A | 112.28 (5) | C1B—C2B—C3B | 111.13 (5) |
N1A—C2A—H4A | 108.09 (3) | N1B—C2B—H4B | 109.15 (3) |
C1A—C2A—H4A | 108.09 (3) | C1B—C2B—H4B | 109.15 (3) |
C3A—C2A—H4A | 108.09 (3) | C3B—C2B—H4B | 109.15 (4) |
C4A—C3A—C5A | 112.25 (6) | C4B—C3B—C5B | 111.04 (7) |
C4A—C3A—C2A | 109.76 (6) | C4B—C3B—C2B | 111.30 (6) |
C5A—C3A—C2A | 112.31 (5) | C5B—C3B—C2B | 111.08 (7) |
C4A—C3A—H5A | 107.42 (4) | C4B—C3B—H5B | 107.75 (5) |
C5A—C3A—H5A | 107.42 (4) | C5B—C3B—H5B | 107.75 (5) |
C2A—C3A—H5A | 107.42 (3) | C2B—C3B—H5B | 107.75 (3) |
C3A—C4A—H6A | 109.47 (5) | C3B—C4B—H6B | 109.47 (5) |
C3A—C4A—H7A | 109.47 (4) | C3B—C4B—H7B | 109.47 (4) |
H6A—C4A—H7A | 109.5 | H6B—C4B—H7B | 109.5 |
C3A—C4A—H8A | 109.47 (4) | C3B—C4B—H8B | 109.47 (5) |
H6A—C4A—H8A | 109.5 | H6B—C4B—H8B | 109.5 |
H7A—C4A—H8A | 109.5 | H7B—C4B—H8B | 109.5 |
C6A—C5A—C3A | 113.72 (7) | C6B—C5B—C3B | 113.29 (5) |
C6A—C5A—H9A | 108.82 (5) | C6B—C5B—H9B | 108.9 |
C3A—C5A—H9A | 108.82 (4) | C3B—C5B—H9B | 108.92 (4) |
C6A—C5A—H10A | 108.82 (5) | C6B—C5B—H10B | 108.9 |
C3A—C5A—H10A | 108.82 (4) | C3B—C5B—H10B | 108.92 (4) |
H9A—C5A—H10A | 107.7 | H9B—C5B—H10B | 107.7 |
C5A—C6A—H11A | 109.47 (5) | C5B—C6B—H11B | 109.5 |
C5A—C6A—H12A | 109.47 (5) | C5B—C6B—H12B | 109.5 |
H11A—C6A—H12A | 109.5 | H11B—C6B—H12B | 109.5 |
C5A—C6A—H13A | 109.47 (5) | C5B—C6B—H13B | 109.5 |
H11A—C6A—H13A | 109.5 | H11B—C6B—H13B | 109.5 |
H12A—C6A—H13A | 109.5 | H12B—C6B—H13B | 109.5 |
| | | |
O1A—C1A—C2A—N1A | 17.68 (8) | O2B—C1B—C2B—N1B | −138.86 (7) |
O2A—C1A—C2A—N1A | −164.38 (5) | O1B—C1B—C2B—N1B | 43.22 (7) |
O1A—C1A—C2A—C3A | −105.68 (6) | O2B—C1B—C2B—C3B | 100.70 (7) |
O2A—C1A—C2A—C3A | 72.27 (7) | O1B—C1B—C2B—C3B | −77.23 (7) |
N1A—C2A—C3A—C4A | 152.47 (6) | N1B—C2B—C3B—C4B | 56.35 (8) |
C1A—C2A—C3A—C4A | −84.83 (7) | C1B—C2B—C3B—C4B | 176.62 (7) |
N1A—C2A—C3A—C5A | −81.92 (7) | N1B—C2B—C3B—C5B | −179.37 (6) |
C1A—C2A—C3A—C5A | 40.78 (8) | C1B—C2B—C3B—C5B | −59.10 (7) |
C4A—C3A—C5A—C6A | −61.08 (9) | C4B—C3B—C5B—C6B | −65.87 (6) |
C2A—C3A—C5A—C6A | 174.68 (7) | C2B—C3B—C5B—C6B | 169.71 (3) |