Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107014838/sn5050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107014838/sn5050sup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768107014838/sn5050sup3.pdf |
CCDC reference: 650667
Data collection: CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5; cell refinement: CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5; data reduction: CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5; program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: PLATON, (Spek, 2003); software used to prepare material for publication: publCIF (Westrip, 2006).
C5H13N2O2·Cl | F(000) = 180.0 |
Mr = 168.62 | Dx = 1.429 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: P2yb | Cell parameters from 24585 reflections |
a = 9.9480 (2) Å | θ = 3.3–52.7° |
b = 7.9637 (2) Å | µ = 0.43 mm−1 |
c = 4.9826 (1) Å | T = 100 K |
β = 83.13 (1)° | Rectangle, colourless |
V = 391.91 (2) Å3 | 0.71 × 0.63 × 0.24 mm |
Z = 2 |
Oxford Diffraction Xcalibur S diffractometer | 8892 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 8123 reflections with F > 3σ (F) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 16.0009 pixels mm-1 | θmax = 52.7°, θmin = 3.3° |
ω scans | h = −22→22 |
Absorption correction: analytical CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5, (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) | k = −17→17 |
Tmin = 0.790, Tmax = 0.914 | l = −11→11 |
34435 measured reflections |
Refinement on F | All H-atom parameters refined |
Least-squares matrix: full | w1 = 1/[s2(Fo)] |
R[F2 > 2σ(F2)] = 0.014 | (Δ/σ)max < 0.001 |
wR(F2) = 0.009 | Δρmax = 0.33 e Å−3 |
S = 1.80 | Δρmin = −0.45 e Å−3 |
8123 reflections | Absolute structure: (Dittrich et al., 2006c) |
103 parameters | Absolute structure parameter: −0.00 (7) |
0 restraints |
C5H13N2O2·Cl | V = 391.91 (2) Å3 |
Mr = 168.62 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.9480 (2) Å | µ = 0.43 mm−1 |
b = 7.9637 (2) Å | T = 100 K |
c = 4.9826 (1) Å | 0.71 × 0.63 × 0.24 mm |
β = 83.13 (1)° |
Oxford Diffraction Xcalibur S diffractometer | 8892 independent reflections |
Absorption correction: analytical CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5, (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) | 8123 reflections with F > 3σ (F) |
Tmin = 0.790, Tmax = 0.914 | Rint = 0.020 |
34435 measured reflections |
R[F2 > 2σ(F2)] = 0.014 | All H-atom parameters refined |
wR(F2) = 0.009 | Δρmax = 0.33 e Å−3 |
S = 1.80 | Δρmin = −0.45 e Å−3 |
8123 reflections | Absolute structure: (Dittrich et al., 2006c) |
103 parameters | Absolute structure parameter: −0.00 (7) |
0 restraints |
Experimental. A nitrogen gas-flow low temperature device was used. A face indexed analytical absorption correction was performed. |
x | y | z | Uiso*/Ueq | ||
CL1 | 0.420733 (4) | 0.220613 | 0.401602 (9) | 0.011 | |
O1 | −0.00485 (2) | −0.06033 (2) | −0.17400 (3) | 0.011 | |
O2 | −0.095930 (10) | −0.06593 (2) | 0.25880 (3) | 0.012 | |
N1 | 0.10999 (2) | 0.14325 (2) | 0.39039 (3) | 0.009 | |
N2 | 0.35613 (2) | −0.53068 (2) | −0.07902 (3) | 0.011 | |
C1 | −0.00159 (2) | −0.03766 (2) | 0.07543 (4) | 0.008 | |
C2 | 0.13384 (2) | 0.02295 (2) | 0.16088 (4) | 0.008 | |
C3 | 0.21365 (2) | −0.12686 (3) | 0.25227 (4) | 0.01 | |
C4 | 0.25894 (2) | −0.24816 (2) | 0.02337 (4) | 0.01 | |
C5 | 0.32130 (2) | −0.40292 (3) | 0.13674 (4) | 0.011 | |
H1 | 0.0647 (5) | 0.2507 (8) | 0.3347 (9) | 0.0280 (10) | |
H2 | 0.2017 (5) | 0.1780 (6) | 0.4382 (9) | 0.0230 (10) | |
H3 | 0.0551 (5) | 0.0849 (7) | 0.5542 (11) | 0.0250 (10) | |
H4 | 0.1908 (4) | 0.0873 (5) | −0.0031 (9) | 0.0200 (9) | |
H5 | 0.3001 (5) | −0.0776 (6) | 0.3379 (9) | 0.0240 (10) | |
H6 | 0.1495 (5) | −0.1922 (6) | 0.4114 (10) | 0.0260 (10) | |
H7 | 0.3315 (5) | −0.1891 (6) | −0.1273 (10) | 0.0290 (10) | |
H8 | 0.1734 (4) | −0.2873 (8) | −0.0786 (8) | 0.0274 (9) | |
H9 | 0.4125 (5) | −0.3773 (7) | 0.2154 (9) | 0.0290 (10) | |
H10 | 0.2505 (5) | −0.4607 (6) | 0.2924 (10) | 0.0290 (10) | |
H11 | 0.3937 (5) | −0.6356 (7) | 0.0088 (10) | 0.0250 (10) | |
H12 | 0.4292 (5) | −0.4850 (7) | −0.2211 (11) | 0.0280 (10) | |
H13 | 0.2716 (5) | −0.5613 (7) | −0.1646 (10) | 0.0290 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
CL1 | 0.009330 (10) | 0.01104 (2) | 0.01374 (2) | 0.00076 (2) | −0.002140 (10) | −0.00067 (2) |
O1 | 0.01336 (6) | 0.01290 (6) | 0.00732 (5) | −0.00236 (5) | −0.00265 (4) | −0.00088 (4) |
O2 | 0.00875 (5) | 0.01801 (7) | 0.00915 (5) | −0.00275 (5) | −0.00125 (4) | 0.00268 (5) |
N1 | 0.00948 (6) | 0.00832 (6) | 0.00897 (5) | 0.00040 (5) | −0.00162 (4) | −0.00189 (5) |
N2 | 0.01110 (6) | 0.00929 (6) | 0.01227 (6) | 0.00205 (5) | −0.00182 (5) | −0.00204 (5) |
C1 | 0.00839 (6) | 0.00860 (6) | 0.00662 (5) | −0.00060 (5) | −0.00163 (5) | 0.00032 (5) |
C2 | 0.00796 (6) | 0.00784 (6) | 0.00775 (6) | −0.00013 (5) | −0.00105 (5) | −0.00103 (5) |
C3 | 0.00957 (6) | 0.00888 (7) | 0.01015 (6) | 0.00177 (5) | −0.00235 (5) | −0.00163 (5) |
C4 | 0.01163 (6) | 0.00907 (8) | 0.01030 (6) | 0.00229 (5) | −0.00127 (5) | −0.00120 (5) |
C5 | 0.01183 (7) | 0.00898 (7) | 0.01071 (7) | 0.00187 (5) | −0.00278 (5) | −0.00148 (5) |
O1—C1 | 1.2601 (2) | C2—H4 | 1.068 (4) |
O2—C1 | 1.2495 (2) | C3—C4 | 1.5212 (3) |
N1—H1 | 1.020 (6) | C3—H5 | 1.079 (5) |
N1—H2 | 1.008 (5) | C3—H6 | 1.089 (5) |
N1—H3 | 1.036 (5) | C4—C5 | 1.5187 (3) |
N2—H11 | 1.034 (6) | C4—H7 | 1.085 (5) |
N2—H12 | 1.019 (6) | C4—H8 | 1.087 (4) |
N2—H13 | 1.017 (5) | C5—H9 | 1.051 (5) |
C1—C2 | 1.5383 (2) | C5—H10 | 1.086 (5) |
C2—C3 | 1.5321 (3) | ||
H1—N1—H2 | 106.0 (4) | C2—C3—H6 | 108.0 (2) |
H1—N1—H3 | 112.5 (4) | C4—C3—H5 | 110.4 (2) |
H2—N1—H3 | 110.1 (4) | C4—C3—H6 | 109.7 (3) |
H11—N2—H12 | 108.6 (4) | H5—C3—H6 | 108.1 (3) |
H11—N2—H13 | 110.0 (4) | C3—C4—C5 | 109.511 (15) |
H12—N2—H13 | 110.6 (4) | C3—C4—H7 | 110.9 (3) |
O1—C1—O2 | 126.138 (18) | C3—C4—H8 | 110.7 (3) |
O1—C1—C2 | 116.395 (15) | C5—C4—H7 | 110.0 (3) |
O2—C1—C2 | 117.405 (16) | C5—C4—H8 | 108.5 (3) |
C1—C2—C3 | 109.876 (15) | H7—C4—H8 | 107.1 (3) |
C1—C2—H4 | 109.9 (2) | C4—C5—H9 | 113.0 (3) |
C3—C2—H4 | 110.8 (2) | C4—C5—H10 | 110.5 (3) |
C2—C3—C4 | 112.905 (15) | H9—C5—H10 | 109.4 (3) |
C2—C3—H5 | 107.5 (3) |
Experimental details
Crystal data | |
Chemical formula | C5H13N2O2·Cl |
Mr | 168.62 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 9.9480 (2), 7.9637 (2), 4.9826 (1) |
β (°) | 83.13 (1) |
V (Å3) | 391.91 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.43 |
Crystal size (mm) | 0.71 × 0.63 × 0.24 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur S diffractometer |
Absorption correction | Analytical CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5, (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) |
Tmin, Tmax | 0.790, 0.914 |
No. of measured, independent and observed [F > 3σ (F)] reflections | 34435, 8892, 8123 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 1.119 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.014, 0.009, 1.80 |
No. of reflections | 8123 |
No. of parameters | 103 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.33, −0.45 |
Absolute structure | (Dittrich et al., 2006c) |
Absolute structure parameter | −0.00 (7) |
Computer programs: CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5, CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5, Koritsanszky et al., (2003), PLATON, (Spek, 2003), publCIF (Westrip, 2006).
Bond | IAM | Invariom | Multipole |
O1—C1 | 1.2614 (4) | 1.2601 (2) | 1.2599 (3) |
O(2) - C(1) | 1.2513 (4) | 1.2495 (2) | 1.2503 (3) |
N(1) - H(1) | 0.836 (9) | 1.020 (6) | — |
N(1) - H(2) | 0.857 (7) | 1.008 (5) | — |
N(1) - H(3) | 0.864 (8) | 1.036 (5) | — |
N(2) - H(11) | 0.869 (8) | 1.034 (6) | — |
N(2) - H(12) | 0.886 (8) | 1.019 (6) | — |
N(2) - H(13) | 0.879 (8) | 1.017 (5) | — |
C(1) - C(2) | 1.5391 (4) | 1.5383 (2) | 1.5396 (3) |
C(2) - C(3) | 1.5310 (5) | 1.5321 (3) | 1.5323 (3) |
C(2) - H(4) | 0.932 (7) | 1.068 (4) | — |
C(3) - C(4) | 1.5217 (5) | 1.5212 (3) | 1.5214 (3) |
C(3) - H(5) | 0.991 (7) | 1.079 (5) | — |
C(3) - H(6) | 0.950 (7) | 1.089 (5) | — |
C(4) - C(5) | 1.5187 (5) | 1.5187 (3) | 1.5193 (3) |
C(4) - H(7) | 0.981 (7) | 1.085 (5) | — |
C(4) - H(8) | 0.984 (7) | 1.087 (4) | — |
C(5) - H(9) | 0.963 (7) | 1.051 (5) | — |
C(5) - H(10) | 0.921 (7) | 1.086 (5) | — |
Donor | H | Acceptor | Symmetry | D···H | H···A | D···A | Angle DHA |
N1 | H1 | O1 | -x,1/2 + y,-z | 1.021 (6) | 1.837 (6) | 2.8458 (2) | 169.1 (4) |
N1 | H2 | Cl | intra | 1.009 (5) | 2.191 (5) | 3.1591 (2) | 160.3 (4) |
N1 | H3 | O1 | x,y,1 + z | 1.036 (5) | 1.826 (5) | 2.8376 (2) | 164.3 (5) |
N2 | H11 | Cl | x,-1 + y,z | 1.034 (5) | 2.311 (5) | 3.2309 (2) | 147.5 (4) |
N2 | H12 | Cl | 1 − x,-1/2 + y,-z | 1.019 (5) | 2.323 (5) | 3.2654 (2) | 153.2 (4) |
N2 | H13 | O2 | -x,-1/2 + y,-z | 1.017 (5) | 1.863 (5) | 2.8523 (2) | 163.3 (5) |
C3 | H5 | Cl | intra | 1.079 (5) | 2.697 (5) | 3.5807 (2) | 138.9 (3) |
C4 | H7 | Cl | 1 − x,-1/2 + y,-z | 1.085 (5) | 2.767 (5) | 3.6176 (2) | 135.2 (3) |
C4 | H8 | O2 | -x,-1/2 + y,-z | 1.088 (4) | 2.547 (6) | 3.3993 (2) | 134.5 (4) |
C5 | H9 | Cl | 1 − x,-1/2 + y,1 − z | 1.050 (5) | 2.786 (5) | 3.7757 (2) | 157.2 (3) |
Compound | V/Z | Σn2core | S |
L-ornithine hydrochloride | 196.0 | 136 | 1.44 |
L-valinol | 160.2 | 28 | 5.72 |
4-O-methylalpinumisoflavone | 419.4 | 104 | 4.03 |
O,O-dimethylalpinumisoflavone | 447.5 | 108 | 4.14 |
5-O-methyl-4-O-(3-methylbut-2-en-1-yl)alpinumisoflavone | 1111.8 | 248 | 4.48 |