Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100013975/oa0030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030ileNH2sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030valNH2sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030thrNH2sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030metNH2sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030trpNH2sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030glnNH2sup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030argNH2sup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030serNH2sup9.hkl |
CCDC references: 159961; 159962; 159963; 159964; 159965; 159966; 159967; 159968
For all compounds, data collection: MSC/AFC (Molecular Structure Corp. 1991); cell refinement: MSC/AFC (Molecular Structure Corp. 1991); data reduction: MSC/AFC (Molecular Structure Corp. 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C6H15N2O+·Cl− | F(000) = 180 |
Mr = 166.65 | Dx = 1.190 Mg m−3 Dm = 1.221 (5) Mg m−3 Dm measured by measured |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2y1 | Cell parameters from 25 reflections |
a = 7.5775 (13) Å | θ = 0.3–65.0° |
b = 4.8971 (13) Å | µ = 3.20 mm−1 |
c = 12.5686 (14) Å | T = 293 K |
β = 94.195 (12)° | Plate, colourless |
V = 465.14 (16) Å3 | 0.6 × 0.4 × 0.05 mm |
Z = 2 |
Rigaku AFC5R diffractometer | 817 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 65.0°, θmin = 3.5° |
ω–2θ scans | h = 0→8 |
Absorption correction: ψ-scan North, et al., 1990 | k = −5→0 |
Tmin = 0.629, Tmax = 0.999 | l = −14→14 |
963 measured reflections | 3 standard reflections every 100 reflections |
893 independent reflections | intensity decay: 2% |
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)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.187 | Calculated w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.66 | (Δ/σ)max = 0.094 |
893 reflections | Δρmax = 0.70 e Å−3 |
90 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.04 (5) |
C6H15N2O+·Cl− | V = 465.14 (16) Å3 |
Mr = 166.65 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 7.5775 (13) Å | µ = 3.20 mm−1 |
b = 4.8971 (13) Å | T = 293 K |
c = 12.5686 (14) Å | 0.6 × 0.4 × 0.05 mm |
β = 94.195 (12)° |
Rigaku AFC5R diffractometer | 817 reflections with I > 2σ(I) |
Absorption correction: ψ-scan North, et al., 1990 | Rint = 0.052 |
Tmin = 0.629, Tmax = 0.999 | 3 standard reflections every 100 reflections |
963 measured reflections | intensity decay: 2% |
893 independent reflections |
R[F2 > 2σ(F2)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.187 | Δρmax = 0.70 e Å−3 |
S = 1.66 | Δρmin = −0.29 e Å−3 |
893 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
90 parameters | Absolute structure parameter: −0.04 (5) |
0 restraints |
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.52108 (13) | 0.6504 | 0.62484 (10) | 0.0460 (5) | |
N1 | −0.2267 (5) | 1.1570 (14) | 0.5937 (3) | 0.0364 (9) | |
H1A | −0.2103 | 1.1621 | 0.5219 | 0.044* | |
H1B | −0.2803 | 0.9893 | 0.6014 | 0.044* | |
H1C | −0.2970 | 1.3129 | 0.6052 | 0.044* | |
C1 | −0.0721 (6) | 1.1726 (14) | 0.6735 (3) | 0.0345 (11) | |
H1 | −0.0375 | 1.3637 | 0.6853 | 0.041* | |
C1' | 0.0777 (7) | 1.0162 (14) | 0.6266 (4) | 0.0359 (11) | |
O1' | 0.0556 (5) | 0.7854 (10) | 0.5938 (3) | 0.0409 (9) | |
N2 | 0.2334 (5) | 1.1489 (16) | 0.6269 (4) | 0.0498 (11) | |
H2NA | 0.2524 | 1.3614 | 0.6416 | 0.060* | |
H2NB | 0.3220 | 1.0614 | 0.6019 | 0.060* | |
C2 | −0.1145 (7) | 1.0406 (16) | 0.7800 (4) | 0.0442 (13) | |
H2 | −0.1540 | 0.8530 | 0.7651 | 0.053* | |
C3 | −0.2628 (9) | 1.1903 (18) | 0.8297 (5) | 0.063 (2) | |
H3A | −0.2184 | 1.3641 | 0.8574 | 0.075* | |
H3B | −0.3564 | 1.2278 | 0.7749 | 0.075* | |
C4 | 0.0499 (11) | 1.028 (3) | 0.8553 (5) | 0.086 (3) | |
H4A | 0.0222 | 0.9414 | 0.9206 | 0.130* | |
H4B | 0.0926 | 1.2092 | 0.8701 | 0.130* | |
H4C | 0.1393 | 0.9239 | 0.8231 | 0.130* | |
C5 | −0.3392 (14) | 1.033 (3) | 0.9187 (7) | 0.093 (3) | |
H5A | −0.4323 | 1.1379 | 0.9468 | 0.139* | |
H5B | −0.2481 | 0.9995 | 0.9743 | 0.139* | |
H5C | −0.3857 | 0.8626 | 0.8917 | 0.139* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0287 (7) | 0.0366 (7) | 0.0725 (8) | 0.0020 (6) | 0.0025 (5) | 0.0008 (7) |
N1 | 0.0270 (17) | 0.039 (2) | 0.0435 (18) | 0.000 (3) | 0.0066 (14) | 0.002 (3) |
C1 | 0.024 (2) | 0.032 (3) | 0.047 (2) | −0.001 (2) | 0.0026 (17) | −0.005 (3) |
C1' | 0.030 (2) | 0.033 (3) | 0.044 (2) | 0.002 (3) | 0.0024 (18) | 0.000 (2) |
O1' | 0.0277 (17) | 0.036 (2) | 0.0596 (19) | −0.0024 (16) | 0.0095 (15) | −0.0081 (18) |
N2 | 0.0231 (19) | 0.045 (2) | 0.082 (3) | −0.004 (3) | 0.0072 (18) | −0.009 (4) |
C2 | 0.045 (3) | 0.044 (3) | 0.044 (3) | 0.006 (3) | 0.003 (2) | 0.001 (3) |
C3 | 0.069 (4) | 0.067 (5) | 0.055 (3) | 0.026 (4) | 0.025 (3) | 0.011 (3) |
C4 | 0.071 (5) | 0.137 (9) | 0.050 (3) | 0.010 (6) | −0.009 (3) | 0.012 (5) |
C5 | 0.109 (7) | 0.097 (7) | 0.078 (5) | 0.023 (6) | 0.050 (5) | 0.016 (5) |
N1—C1 | 1.487 (5) | C1'—N2 | 1.347 (8) |
C1—C1' | 1.523 (7) | C2—C4 | 1.510 (8) |
C1—C2 | 1.541 (7) | C2—C3 | 1.515 (8) |
C1'—O1' | 1.211 (7) | C3—C5 | 1.507 (11) |
N1—C1—C1' | 106.6 (4) | N2—C1'—C1 | 115.7 (5) |
N1—C1—C2 | 111.1 (4) | C4—C2—C1 | 110.3 (5) |
C1'—C1—C2 | 109.5 (5) | C4—C2—C3 | 111.4 (5) |
O1'—C1'—N2 | 123.4 (6) | C1—C2—C3 | 111.3 (5) |
O1'—C1'—C1 | 120.9 (5) | C5—C3—C2 | 113.3 (7) |
C5H13N2O+·Cl− | F(000) = 164 |
Mr = 152.62 | Dx = 1.287 Mg m−3 Dm = 1.280 (5) Mg m−3 Dm measured by measured |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2y1 | Cell parameters from 25 reflections |
a = 5.3377 (8) Å | θ = 0.3–65.0° |
b = 7.4572 (9) Å | µ = 3.73 mm−1 |
c = 9.899 (1) Å | T = 293 K |
β = 91.73 (1)° | Plate, colourless |
V = 393.84 (9) Å3 | 0.8 × 0.6 × 0.3 mm |
Z = 2 |
Rigaku AFC5R diffractometer | Rint = 0.135 |
Radiation source: fine-focus sealed tube | θmax = 65.0°, θmin = 4.5° |
Graphite monochromator | h = −6→6 |
ω–2θ scans | k = −8→0 |
1458 measured reflections | l = −11→11 |
731 independent reflections | 3 standard reflections every 100 reflections |
718 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | Calculated w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.097 | (Δ/σ)max = 0.176 |
S = 0.75 | Δρmax = 0.30 e Å−3 |
731 reflections | Δρmin = −0.41 e Å−3 |
82 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2]3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.67 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.009 (16) |
C5H13N2O+·Cl− | V = 393.84 (9) Å3 |
Mr = 152.62 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 5.3377 (8) Å | µ = 3.73 mm−1 |
b = 7.4572 (9) Å | T = 293 K |
c = 9.899 (1) Å | 0.8 × 0.6 × 0.3 mm |
β = 91.73 (1)° |
Rigaku AFC5R diffractometer | Rint = 0.135 |
1458 measured reflections | 3 standard reflections every 100 reflections |
731 independent reflections | intensity decay: 2% |
718 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | (Δ/σ)max = 0.176 |
S = 0.75 | Δρmax = 0.30 e Å−3 |
731 reflections | Δρmin = −0.41 e Å−3 |
82 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
0 restraints | Absolute structure parameter: 0.009 (16) |
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.31763 (9) | 0.3393 | 0.66340 (4) | 0.0355 (4) | |
N1 | −0.2346 (4) | −0.3958 (3) | 0.60582 (16) | 0.0272 (6) | |
H1A | −0.3441 | −0.4822 | 0.6226 | 0.033* | |
H1B | −0.2573 | −0.3679 | 0.5230 | 0.033* | |
H1C | −0.0635 | −0.4562 | 0.6353 | 0.033* | |
C1 | −0.3014 (4) | −0.2353 (3) | 0.68810 (17) | 0.0220 (5) | |
H1 | −0.4620 | −0.1882 | 0.6532 | 0.026* | |
C1' | −0.1014 (5) | −0.0951 (4) | 0.66654 (18) | 0.0256 (6) | |
O1' | 0.1097 (3) | −0.1416 (3) | 0.63338 (18) | 0.0365 (6) | |
N2 | −0.1632 (5) | 0.0743 (4) | 0.6891 (3) | 0.0444 (7) | |
H2NA | −0.0509 | 0.1624 | 0.6714 | 0.053* | |
H2NB | −0.3380 | 0.1294 | 0.6844 | 0.053* | |
C2 | −0.3316 (4) | −0.2894 (4) | 0.83690 (17) | 0.0277 (7) | |
H2 | −0.4541 | −0.3873 | 0.8382 | 0.033* | |
C3 | −0.0910 (6) | −0.3589 (5) | 0.9032 (3) | 0.0469 (8) | |
H3A | −0.0272 | −0.4561 | 0.8508 | 0.070* | |
H3B | −0.1240 | −0.4005 | 0.9927 | 0.070* | |
H3C | 0.0307 | −0.2641 | 0.9082 | 0.070* | |
C4 | −0.4375 (5) | −0.1360 (5) | 0.9175 (2) | 0.0443 (8) | |
H4A | −0.5892 | −0.0938 | 0.8737 | 0.067* | |
H4B | −0.3176 | −0.0401 | 0.9229 | 0.067* | |
H4C | −0.4728 | −0.1767 | 1.0069 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0345 (5) | 0.0361 (5) | 0.0363 (5) | −0.0124 (3) | 0.0065 (2) | −0.0077 (2) |
N1 | 0.0302 (11) | 0.0277 (10) | 0.0240 (8) | −0.0050 (9) | 0.0068 (7) | −0.0021 (7) |
C1 | 0.0170 (10) | 0.0272 (11) | 0.0221 (8) | −0.0010 (9) | 0.0034 (7) | −0.0009 (8) |
C1' | 0.0275 (11) | 0.0250 (11) | 0.0245 (10) | −0.0036 (12) | 0.0037 (7) | 0.0007 (8) |
O1' | 0.0198 (9) | 0.0397 (12) | 0.0504 (9) | −0.0018 (9) | 0.0088 (6) | 0.0035 (8) |
N2 | 0.0392 (15) | 0.0257 (11) | 0.0692 (13) | −0.0018 (12) | 0.0175 (11) | 0.0017 (12) |
C2 | 0.0271 (13) | 0.0341 (16) | 0.0223 (11) | −0.0070 (10) | 0.0070 (9) | −0.0002 (8) |
C3 | 0.0467 (16) | 0.0622 (18) | 0.0317 (10) | 0.0034 (16) | 0.0008 (10) | 0.0143 (14) |
C4 | 0.0445 (14) | 0.055 (2) | 0.0347 (11) | −0.0070 (16) | 0.0133 (11) | −0.0124 (13) |
N1—C1 | 1.497 (3) | C1'—N2 | 1.327 (4) |
C1—C1' | 1.514 (4) | C2—C3 | 1.516 (4) |
C1—C2 | 1.540 (2) | C2—C4 | 1.514 (4) |
C1'—O1' | 1.233 (3) | ||
N1—C1—C1' | 107.15 (15) | N2—C1'—C1 | 117.0 (2) |
N1—C1—C2 | 110.2 (2) | C3—C2—C4 | 110.8 (2) |
C1'—C1—C2 | 114.23 (18) | C3—C2—C1 | 113.06 (17) |
O1'—C1'—N2 | 123.1 (3) | C4—C2—C1 | 110.9 (3) |
O1'—C1'—C1 | 119.8 (2) |
C4H11N2O2+·Cl− | Dx = 1.417 Mg m−3 Dm = 1.402 (5) Mg m−3 Dm measured by measured |
Mr = 154.60 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 10.1624 (15) Å | θ = 0.3–63.1° |
b = 10.5673 (17) Å | µ = 4.17 mm−1 |
c = 6.749 (3) Å | T = 293 K |
V = 724.8 (3) Å3 | Cubic, colourless |
Z = 4 | 0.8 × 0.6 × 0.6 mm |
F(000) = 328 |
Rigaku AFC5R diffractometer | 710 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 63.1°, θmin = 6.0° |
ω–2θ scans | h = 0→11 |
Absorption correction: ψ-scan North, et al., 1990 | k = 0→12 |
Tmin = 0.782, Tmax = 0.999 | l = −7→0 |
710 measured reflections | 3 standard reflections every 100 reflections |
710 independent reflections | intensity decay: 2% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.047 | Calculated w = 1/[σ2(Fo2) + (0.0986P)2 + 0.4071P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.121 | (Δ/σ)max = 0.049 |
S = 1.10 | Δρmax = 0.50 e Å−3 |
710 reflections | Δρmin = −0.59 e Å−3 |
83 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.34 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.06 (3) |
C4H11N2O2+·Cl− | V = 724.8 (3) Å3 |
Mr = 154.60 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 10.1624 (15) Å | µ = 4.17 mm−1 |
b = 10.5673 (17) Å | T = 293 K |
c = 6.749 (3) Å | 0.8 × 0.6 × 0.6 mm |
Rigaku AFC5R diffractometer | 710 reflections with I > 2σ(I) |
Absorption correction: ψ-scan North, et al., 1990 | Rint = 0.000 |
Tmin = 0.782, Tmax = 0.999 | 3 standard reflections every 100 reflections |
710 measured reflections | intensity decay: 2% |
710 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.121 | Δρmax = 0.50 e Å−3 |
S = 1.10 | Δρmin = −0.59 e Å−3 |
710 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
83 parameters | Absolute structure parameter: 0.06 (3) |
0 restraints |
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.96087 (8) | 0.37191 (8) | 0.35803 (13) | 0.0172 (5) | |
N1 | 0.6071 (3) | 0.8326 (3) | 0.5331 (4) | 0.0130 (8) | |
H1A | 0.5984 | 0.7678 | 0.6315 | 0.016* | |
H1B | 0.6741 | 0.8889 | 0.5626 | 0.016* | |
H1C | 0.5178 | 0.8817 | 0.5110 | 0.016* | |
C1 | 0.6337 (3) | 0.7750 (3) | 0.3361 (5) | 0.0078 (8) | |
H1 | 0.5559 | 0.7268 | 0.2952 | 0.009* | |
C1' | 0.7493 (3) | 0.6832 (3) | 0.3592 (6) | 0.0102 (8) | |
O1' | 0.8240 (3) | 0.6913 (3) | 0.5026 (4) | 0.0216 (8) | |
N2 | 0.7622 (3) | 0.5989 (3) | 0.2159 (5) | 0.0213 (9) | |
H2NA | 0.8351 | 0.5333 | 0.2381 | 0.026* | |
H2NB | 0.6907 | 0.5922 | 0.1159 | 0.026* | |
C2 | 0.6600 (4) | 0.8772 (3) | 0.1821 (5) | 0.0125 (9) | |
H2 | 0.6876 | 0.8373 | 0.0578 | 0.015* | |
C3 | 0.5383 (4) | 0.9558 (4) | 0.1451 (7) | 0.0230 (10) | |
H3A | 0.5575 | 1.0198 | 0.0485 | 0.034* | |
H3B | 0.5110 | 0.9952 | 0.2665 | 0.034* | |
H3C | 0.4690 | 0.9023 | 0.0968 | 0.034* | |
O4 | 0.7611 (2) | 0.9587 (2) | 0.2494 (4) | 0.0175 (7) | |
H4 | 0.8359 | 0.9158 | 0.2558 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0136 (6) | 0.0217 (7) | 0.0163 (7) | −0.0004 (3) | 0.0039 (4) | 0.0026 (4) |
N1 | 0.0121 (16) | 0.0158 (15) | 0.0110 (15) | 0.0010 (13) | 0.0040 (13) | 0.0019 (15) |
C1 | 0.0037 (16) | 0.0103 (16) | 0.0094 (18) | −0.0018 (12) | −0.0002 (14) | −0.0035 (15) |
C1' | 0.0017 (14) | 0.0163 (17) | 0.0125 (17) | −0.0019 (14) | −0.0015 (16) | 0.0041 (16) |
O1' | 0.0139 (14) | 0.0356 (16) | 0.0154 (14) | 0.0094 (13) | −0.0075 (12) | −0.0025 (14) |
N2 | 0.0131 (16) | 0.0233 (16) | 0.0275 (19) | 0.0094 (13) | −0.0100 (16) | −0.0093 (16) |
C2 | 0.0089 (17) | 0.0168 (19) | 0.0119 (18) | 0.0040 (16) | −0.0015 (15) | −0.0014 (15) |
C3 | 0.015 (2) | 0.032 (2) | 0.022 (2) | 0.0084 (15) | 0.001 (2) | 0.010 (2) |
O4 | 0.0101 (12) | 0.0177 (13) | 0.0246 (16) | −0.0051 (11) | −0.0022 (14) | 0.0054 (13) |
N1—C1 | 1.487 (4) | C1'—N2 | 1.322 (5) |
C1—C1' | 1.531 (5) | C2—O4 | 1.415 (4) |
C1—C2 | 1.523 (5) | C2—C3 | 1.511 (5) |
C1'—O1' | 1.233 (4) | ||
N1—C1—C1' | 107.9 (3) | N2—C1'—C1 | 115.4 (3) |
N1—C1—C2 | 110.6 (3) | O4—C2—C3 | 108.2 (3) |
C1'—C1—C2 | 112.6 (3) | O4—C2—C1 | 109.9 (3) |
O1'—C1'—N2 | 124.0 (3) | C3—C2—C1 | 111.0 (3) |
O1'—C1'—C1 | 120.6 (3) |
C3H9N2O2+·Cl− | F(000) = 148 |
Mr = 140.57 | Dx = 1.450 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2y1 | Cell parameters from 25 reflections |
a = 7.562 (2) Å | θ = 0.3–67.4° |
b = 4.9986 (18) Å | µ = 4.64 mm−1 |
c = 8.519 (3) Å | T = 293 K |
β = 90.76 (3)° | Plate, colourless |
V = 322.00 (18) Å3 | 0.8 × 0.2 × 0.05 mm |
Z = 2 |
Rigaku AFC5R diffractometer | 626 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 67.4°, θmin = 5.2° |
ω–2θ scans | h = 0→9 |
Absorption correction: ψ-scan North, et al., 1990 | k = 0→5 |
Tmin = 0.464, Tmax = 0.793 | l = −10→10 |
687 measured reflections | 3 standard reflections every 100 reflections |
638 independent reflections | intensity decay: 2% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[\<i>w2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.162 | (Δ/σ)max = 0.003 |
S = 1.58 | Δρmax = 0.42 e Å−3 |
638 reflections | Δρmin = −0.50 e Å−3 |
73 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2]3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.050 (14) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.01 (4) |
C3H9N2O2+·Cl− | V = 322.00 (18) Å3 |
Mr = 140.57 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 7.562 (2) Å | µ = 4.64 mm−1 |
b = 4.9986 (18) Å | T = 293 K |
c = 8.519 (3) Å | 0.8 × 0.2 × 0.05 mm |
β = 90.76 (3)° |
Rigaku AFC5R diffractometer | 626 reflections with I > 2σ(I) |
Absorption correction: ψ-scan North, et al., 1990 | Rint = 0.050 |
Tmin = 0.464, Tmax = 0.793 | 3 standard reflections every 100 reflections |
687 measured reflections | intensity decay: 2% |
638 independent reflections |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.162 | Δρmax = 0.42 e Å−3 |
S = 1.58 | Δρmin = −0.50 e Å−3 |
638 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
73 parameters | Absolute structure parameter: −0.01 (4) |
0 restraints |
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.00171 (12) | 0.6838 | 0.78990 (13) | 0.0386 (6) | |
N1 | 0.7562 (4) | 0.6763 (11) | 0.1141 (4) | 0.0275 (9) | |
H1A | 0.8326 | 0.5268 | 0.1296 | 0.033* | |
H1B | 0.8350 | 0.8265 | 0.1235 | 0.033* | |
H1C | 0.7232 | 0.6662 | 0.0213 | 0.033* | |
C1 | 0.6193 (5) | 0.6279 (9) | 0.2351 (4) | 0.0238 (11) | |
H1 | 0.5803 | 0.4413 | 0.2282 | 0.029* | |
C1' | 0.4649 (6) | 0.8074 (10) | 0.1998 (4) | 0.0224 (10) | |
N2 | 0.3120 (5) | 0.7451 (10) | 0.2644 (5) | 0.0387 (12) | |
H2NA | 0.2111 | 0.8826 | 0.2582 | 0.046* | |
H2NB | 0.3481 | 0.7023 | 0.3709 | 0.046* | |
O1' | 0.4840 (4) | 1.0101 (7) | 0.1163 (4) | 0.0289 (8) | |
C2 | 0.6940 (6) | 0.6800 (14) | 0.4002 (4) | 0.0317 (10) | |
H2A | 0.6170 | 0.5978 | 0.4766 | 0.038* | |
H2B | 0.8093 | 0.5964 | 0.4101 | 0.038* | |
O3 | 0.7104 (5) | 0.9590 (9) | 0.4346 (3) | 0.0393 (10) | |
H3 | 0.7685 | 0.9829 | 0.5442 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0274 (7) | 0.0285 (8) | 0.0601 (8) | −0.0052 (5) | 0.0039 (4) | −0.0005 (5) |
N1 | 0.0257 (16) | 0.0281 (19) | 0.0288 (14) | 0.002 (2) | −0.0005 (12) | −0.0068 (18) |
C1 | 0.0233 (19) | 0.018 (3) | 0.0302 (16) | 0.0057 (16) | −0.0008 (14) | 0.0014 (16) |
C1' | 0.0240 (17) | 0.018 (2) | 0.0255 (15) | −0.0018 (19) | −0.0031 (13) | 0.0010 (16) |
N2 | 0.0234 (18) | 0.036 (3) | 0.057 (2) | 0.0065 (18) | 0.0055 (16) | 0.011 (2) |
O1' | 0.0267 (15) | 0.0214 (17) | 0.0387 (13) | 0.0040 (14) | 0.0001 (12) | 0.0071 (14) |
C2 | 0.033 (2) | 0.035 (2) | 0.0272 (17) | 0.005 (3) | −0.0036 (14) | 0.004 (2) |
O3 | 0.0399 (17) | 0.045 (2) | 0.0329 (15) | 0.0029 (17) | −0.0013 (13) | −0.0116 (17) |
N1—C1 | 1.491 (5) | C1'—O1' | 1.247 (6) |
C1—C1' | 1.500 (6) | C1'—N2 | 1.324 (6) |
C1—C2 | 1.531 (5) | C2—O3 | 1.430 (8) |
N1—C1—C1' | 108.0 (3) | O1'—C1'—C1 | 120.3 (4) |
N1—C1—C2 | 110.9 (3) | N2—C1'—C1 | 117.2 (4) |
C1'—C1—C2 | 111.1 (4) | O3—C2—C1 | 112.6 (4) |
O1'—C1'—N2 | 122.4 (4) |
C5H13N2OS+·Cl− | F(000) = 196 |
Mr = 184.68 | Dx = 1.372 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2y1 | Cell parameters from 25 reflections |
a = 7.591 (3) Å | θ = 0.3–67.5° |
b = 5.029 (3) Å | µ = 5.51 mm−1 |
c = 11.786 (4) Å | T = 293 K |
β = 96.49 (3)° | Plate, colourless |
V = 447.0 (4) Å3 | 0.7 × 0.2 × 0.05 mm |
Z = 2 |
Rigaku AFC5R diffractometer | 811 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 67.5°, θmin = 3.8° |
ω–2θ scans | h = −9→9 |
Absorption correction: ψ-scan (north, et al., 1990) ? | k = 0→6 |
Tmin = 0.697, Tmax = 0.759 | l = −13→0 |
907 measured reflections | 3 standard reflections every 100 reflections |
864 independent reflections | intensity decay: 2% |
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)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.163 | w = 1/[\<i>w2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.44 | (Δ/σ)max = 0.249 |
864 reflections | Δρmax = 0.57 e Å−3 |
90 parameters | Δρmin = −0.52 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (5) |
C5H13N2OS+·Cl− | V = 447.0 (4) Å3 |
Mr = 184.68 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 7.591 (3) Å | µ = 5.51 mm−1 |
b = 5.029 (3) Å | T = 293 K |
c = 11.786 (4) Å | 0.7 × 0.2 × 0.05 mm |
β = 96.49 (3)° |
Rigaku AFC5R diffractometer | 811 reflections with I > 2σ(I) |
Absorption correction: ψ-scan (north, et al., 1990) ? | Rint = 0.023 |
Tmin = 0.697, Tmax = 0.759 | 3 standard reflections every 100 reflections |
907 measured reflections | intensity decay: 2% |
864 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.163 | (Δ/σ)max = 0.249 |
S = 1.44 | Δρmax = 0.57 e Å−3 |
864 reflections | Δρmin = −0.52 e Å−3 |
90 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
0 restraints | Absolute structure parameter: 0.01 (5) |
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
Cl | 0.51904 (16) | 0.4730 | 0.64719 (12) | 0.0384 (5) | |
S4 | 0.8109 (2) | 0.4047 (5) | 0.97871 (12) | 0.0431 (5) | |
N1 | 0.7346 (6) | 0.4648 (12) | 1.4153 (3) | 0.0291 (10) | |
H1A | 0.6803 | 0.3142 | 1.4073 | 0.035* | |
H1B | 0.6930 | 0.6258 | 1.4089 | 0.035* | |
H1C | 0.7753 | 0.4624 | 1.4898 | 0.035* | |
C1 | 0.8676 (7) | 0.4039 (13) | 1.3348 (4) | 0.0292 (12) | |
H1 | 0.9039 | 0.2172 | 1.3427 | 0.035* | |
C1' | 1.0272 (8) | 0.5838 (14) | 1.3652 (5) | 0.0300 (13) | |
O1' | 1.0093 (5) | 0.8075 (10) | 1.4009 (4) | 0.0355 (11) | |
N2 | 1.1836 (6) | 0.4804 (14) | 1.3470 (5) | 0.0425 (13) | |
H2NA | 1.2583 | 0.5565 | 1.3601 | 0.051* | |
H2NB | 1.2061 | 0.2906 | 1.3373 | 0.051* | |
C2 | 0.7816 (6) | 0.4573 (14) | 1.2116 (4) | 0.0320 (12) | |
H2A | 0.6671 | 0.3701 | 1.1996 | 0.038* | |
H2B | 0.7630 | 0.6469 | 1.2007 | 0.038* | |
C3 | 0.9003 (8) | 0.3536 (19) | 1.1248 (5) | 0.0468 (19) | |
H3A | 0.9197 | 0.1647 | 1.1375 | 0.056* | |
H3B | 1.0145 | 0.4413 | 1.1380 | 0.056* | |
C5 | 0.6515 (10) | 0.1451 (19) | 0.9597 (7) | 0.056 (2) | |
H5A | 0.5928 | 0.1508 | 0.8832 | 0.084* | |
H5B | 0.5658 | 0.1676 | 1.0129 | 0.084* | |
H5C | 0.7097 | −0.0234 | 0.9727 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0321 (7) | 0.0372 (8) | 0.0472 (8) | 0.0020 (6) | 0.0097 (5) | 0.0016 (7) |
S4 | 0.0492 (9) | 0.0507 (12) | 0.0317 (8) | −0.0083 (7) | 0.0154 (6) | −0.0003 (7) |
N1 | 0.028 (2) | 0.031 (2) | 0.029 (2) | −0.002 (2) | 0.0063 (15) | 0.002 (2) |
C1 | 0.028 (2) | 0.029 (3) | 0.031 (3) | −0.001 (2) | 0.007 (2) | −0.002 (3) |
C1' | 0.026 (3) | 0.035 (3) | 0.028 (3) | −0.002 (3) | 0.000 (2) | 0.002 (3) |
O1' | 0.0278 (19) | 0.032 (3) | 0.046 (2) | −0.0023 (18) | 0.0012 (17) | −0.010 (2) |
N2 | 0.023 (2) | 0.039 (3) | 0.066 (3) | 0.000 (2) | 0.007 (2) | −0.013 (3) |
C2 | 0.030 (2) | 0.038 (3) | 0.029 (2) | −0.005 (3) | 0.007 (2) | −0.001 (3) |
C3 | 0.037 (3) | 0.070 (5) | 0.035 (3) | 0.000 (3) | 0.011 (2) | −0.010 (3) |
C5 | 0.049 (4) | 0.060 (5) | 0.060 (5) | −0.011 (4) | 0.011 (3) | −0.014 (4) |
S4—C5 | 1.777 (8) | C1—C2 | 1.547 (7) |
S4—C3 | 1.797 (6) | C1'—O1' | 1.214 (8) |
N1—C1 | 1.494 (6) | C1'—N2 | 1.335 (8) |
C1—C1' | 1.522 (8) | C2—C3 | 1.529 (8) |
C5—S4—C3 | 101.2 (4) | O1'—C1'—C1 | 121.0 (6) |
N1—C1—C1' | 107.8 (5) | N2—C1'—C1 | 115.4 (6) |
N1—C1—C2 | 108.5 (4) | C3—C2—C1 | 110.5 (5) |
C1'—C1—C2 | 111.0 (5) | C2—C3—S4 | 113.9 (5) |
O1'—C1'—N2 | 123.5 (6) |
C11H14ClN3O | F(000) = 252 |
Mr = 239.70 | Dx = 1.374 Mg m−3 Dm = 1.362 (5) Mg m−3 Dm measured by not measured |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2y1 | Cell parameters from 25 reflections |
a = 7.6394 (11) Å | θ = 0.3–65.0° |
b = 5.2786 (13) Å | µ = 2.78 mm−1 |
c = 14.5967 (14) Å | T = 293 K |
β = 100.047 (10)° | Needle, colourless |
V = 579.59 (17) Å3 | 0.5 × 0.2 × 0.2 mm |
Z = 2 |
Rigaku AFC5R diffractometer | 1100 independent reflections |
Radiation source: fine-focus sealed tube | 1075 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω–2θ scans | θmax = 65.0°, θmin = 3.1° |
Absorption correction: ψ-scan North, et al., 1990 | h = 0→8 |
Tmin = 0.329, Tmax = 0.573 | k = −6→0 |
1188 measured reflections | l = −17→16 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.030 | Calculated w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max = 0.002 |
S = 0.91 | Δρmax = 0.31 e Å−3 |
1100 reflections | Δρmin = −0.19 e Å−3 |
145 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.040 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.008 (17) |
C11H14ClN3O | V = 579.59 (17) Å3 |
Mr = 239.70 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 7.6394 (11) Å | µ = 2.78 mm−1 |
b = 5.2786 (13) Å | T = 293 K |
c = 14.5967 (14) Å | 0.5 × 0.2 × 0.2 mm |
β = 100.047 (10)° |
Rigaku AFC5R diffractometer | 1100 independent reflections |
Absorption correction: ψ-scan North, et al., 1990 | 1075 reflections with I > 2σ(I) |
Tmin = 0.329, Tmax = 0.573 | Rint = 0.038 |
1188 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | Δρmax = 0.31 e Å−3 |
S = 0.91 | Δρmin = −0.19 e Å−3 |
1100 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
145 parameters | Absolute structure parameter: 0.008 (17) |
0 restraints |
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.38566 (7) | 0.7501 | 0.61629 (3) | 0.0430 (3) | |
N1 | 0.3602 (2) | 0.2296 (5) | 0.59678 (12) | 0.0360 (5) | |
H1A | 0.3364 | 0.2508 | 0.5349 | 0.043* | |
H1B | 0.4488 | 0.1030 | 0.6168 | 0.043* | |
H1C | 0.4055 | 0.3954 | 0.6202 | 0.043* | |
C1 | 0.1952 (3) | 0.1336 (5) | 0.62503 (15) | 0.0301 (5) | |
H1 | 0.1500 | −0.0086 | 0.5845 | 0.036* | |
C1' | 0.0596 (3) | 0.3436 (5) | 0.61116 (16) | 0.0343 (6) | |
N2 | −0.1034 (3) | 0.2816 (6) | 0.62450 (16) | 0.0501 (6) | |
H2NA | −0.1884 | 0.4113 | 0.6219 | 0.060* | |
H2NB | −0.1531 | 0.1151 | 0.6191 | 0.060* | |
O1' | 0.1002 (3) | 0.5591 (4) | 0.59308 (16) | 0.0518 (5) | |
C2 | 0.2354 (3) | 0.0391 (5) | 0.72622 (15) | 0.0340 (5) | |
H2A | 0.1258 | −0.0210 | 0.7436 | 0.041* | |
H2B | 0.3161 | −0.1039 | 0.7296 | 0.041* | |
C3 | 0.3162 (3) | 0.2355 (6) | 0.79574 (13) | 0.0326 (5) | |
C4 | 0.2326 (3) | 0.4304 (6) | 0.83237 (16) | 0.0388 (6) | |
H4 | 0.1114 | 0.4643 | 0.8183 | 0.047* | |
C5 | 0.5008 (3) | 0.2535 (5) | 0.83688 (13) | 0.0312 (5) | |
N6 | 0.3539 (3) | 0.5688 (5) | 0.89292 (13) | 0.0421 (6) | |
H6 | 0.3179 | 0.7298 | 0.9217 | 0.051* | |
C7 | 0.5179 (3) | 0.4649 (5) | 0.89691 (14) | 0.0359 (5) | |
C8 | 0.6511 (3) | 0.1112 (5) | 0.82866 (15) | 0.0377 (6) | |
H8 | 0.6420 | −0.0301 | 0.7901 | 0.045* | |
C9 | 0.6831 (3) | 0.5369 (6) | 0.94831 (15) | 0.0435 (6) | |
H9 | 0.6936 | 0.6756 | 0.9882 | 0.052* | |
C10 | 0.8127 (3) | 0.1832 (7) | 0.87855 (16) | 0.0447 (7) | |
H10 | 0.9137 | 0.0899 | 0.8732 | 0.054* | |
C11 | 0.8283 (3) | 0.3947 (7) | 0.93743 (17) | 0.0476 (7) | |
H11 | 0.9398 | 0.4397 | 0.9699 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0474 (4) | 0.0413 (4) | 0.0417 (4) | 0.0092 (3) | 0.0119 (2) | −0.0044 (3) |
N1 | 0.0400 (9) | 0.0348 (12) | 0.0351 (9) | 0.0046 (10) | 0.0118 (7) | 0.0025 (10) |
C1 | 0.0330 (12) | 0.0266 (11) | 0.0301 (10) | 0.0006 (9) | 0.0038 (7) | −0.0010 (9) |
C1' | 0.0388 (13) | 0.0300 (12) | 0.0326 (11) | −0.0012 (11) | 0.0021 (8) | −0.0013 (10) |
N2 | 0.0321 (10) | 0.0441 (14) | 0.0740 (15) | 0.0017 (11) | 0.0086 (9) | 0.0046 (13) |
O1' | 0.0494 (10) | 0.0293 (10) | 0.0774 (13) | 0.0031 (9) | 0.0128 (9) | 0.0112 (10) |
C2 | 0.0375 (10) | 0.0299 (11) | 0.0343 (10) | −0.0021 (10) | 0.0055 (8) | 0.0041 (10) |
C3 | 0.0382 (10) | 0.0331 (12) | 0.0271 (10) | −0.0012 (11) | 0.0077 (8) | 0.0045 (11) |
C4 | 0.0440 (11) | 0.0392 (14) | 0.0340 (11) | 0.0060 (11) | 0.0094 (9) | 0.0021 (11) |
C5 | 0.0400 (10) | 0.0301 (11) | 0.0238 (9) | −0.0013 (12) | 0.0065 (7) | 0.0046 (10) |
N6 | 0.0590 (12) | 0.0351 (12) | 0.0337 (10) | 0.0039 (11) | 0.0123 (9) | −0.0046 (9) |
C7 | 0.0495 (12) | 0.0327 (13) | 0.0265 (10) | −0.0018 (11) | 0.0092 (8) | 0.0005 (10) |
C8 | 0.0428 (12) | 0.0390 (13) | 0.0313 (11) | 0.0003 (11) | 0.0067 (8) | −0.0021 (10) |
C9 | 0.0614 (15) | 0.0406 (14) | 0.0276 (10) | −0.0154 (14) | 0.0056 (10) | −0.0022 (11) |
C10 | 0.0389 (12) | 0.0563 (19) | 0.0381 (12) | −0.0010 (13) | 0.0049 (9) | 0.0011 (13) |
C11 | 0.0452 (12) | 0.0589 (18) | 0.0361 (11) | −0.0143 (14) | 0.0002 (10) | 0.0010 (13) |
N1—C1 | 1.483 (3) | C4—N6 | 1.374 (3) |
C1—C1' | 1.507 (3) | C5—C8 | 1.395 (4) |
C1—C2 | 1.538 (3) | C5—C7 | 1.410 (4) |
C1'—O1' | 1.220 (4) | N6—C7 | 1.360 (3) |
C1'—N2 | 1.334 (3) | C7—C9 | 1.403 (3) |
C2—C3 | 1.506 (3) | C8—C10 | 1.373 (3) |
C3—C4 | 1.368 (4) | C9—C11 | 1.371 (4) |
C3—C5 | 1.436 (3) | C10—C11 | 1.401 (4) |
C1'—C1—N1 | 108.0 (2) | C8—C5—C7 | 119.4 (2) |
C1'—C1—C2 | 112.66 (19) | C8—C5—C3 | 133.7 (2) |
N1—C1—C2 | 109.91 (17) | C7—C5—C3 | 106.9 (2) |
O1'—C1'—N2 | 122.6 (3) | C7—N6—C4 | 109.0 (2) |
O1'—C1'—C1 | 121.4 (2) | N6—C7—C5 | 107.93 (19) |
N2—C1'—C1 | 115.9 (2) | N6—C7—C9 | 130.5 (3) |
C3—C2—C1 | 114.4 (2) | C5—C7—C9 | 121.6 (2) |
C4—C3—C5 | 106.1 (2) | C10—C8—C5 | 118.9 (2) |
C4—C3—C2 | 128.1 (2) | C11—C9—C7 | 117.4 (3) |
C5—C3—C2 | 125.7 (2) | C8—C10—C11 | 121.2 (2) |
C3—C4—N6 | 110.1 (2) | C9—C11—C10 | 121.5 (2) |
C5H12N3O2+·Cl− | F(000) = 192 |
Mr = 181.63 | Dx = 1.477 Mg m−3 Dm = 1.462 (5) Mg m−3 Dm measured by measured |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2y1 | Cell parameters from 25 reflections |
a = 7.741 (2) Å | θ = 0–67.6° |
b = 4.8907 (13) Å | µ = 3.83 mm−1 |
c = 10.8159 (10) Å | T = 293 K |
β = 94.180 (13)° | Needle, colourless |
V = 408.39 (16) Å3 | 0.8 × 0.2 × 0.2 mm |
Z = 2 |
Rigaku AFC5R diffractometer | 812 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.065 |
Graphite monochromator | θmax = 67.6°, θmin = 4.1° |
ω–2θ scans | h = 0→9 |
Absorption correction: ψ-scan North, et al., 1990 | k = 0→5 |
Tmin = 0.355, Tmax = 0.465 | l = −12→12 |
877 measured reflections | 3 standard reflections every 100 reflections |
816 independent reflections | intensity decay: 2% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | Calculated w = 1/[\<i>w2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.137 | (Δ/σ)max = 0.091 |
S = 1.39 | Δρmax = 0.66 e Å−3 |
816 reflections | Δρmin = −0.39 e Å−3 |
100 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2]3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.187 (19) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (3) |
C5H12N3O2+·Cl− | V = 408.39 (16) Å3 |
Mr = 181.63 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 7.741 (2) Å | µ = 3.83 mm−1 |
b = 4.8907 (13) Å | T = 293 K |
c = 10.8159 (10) Å | 0.8 × 0.2 × 0.2 mm |
β = 94.180 (13)° |
Rigaku AFC5R diffractometer | 812 reflections with I > 2σ(I) |
Absorption correction: ψ-scan North, et al., 1990 | Rint = 0.065 |
Tmin = 0.355, Tmax = 0.465 | 3 standard reflections every 100 reflections |
877 measured reflections | intensity decay: 2% |
816 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.137 | Δρmax = 0.66 e Å−3 |
S = 1.39 | Δρmin = −0.39 e Å−3 |
816 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
100 parameters | Absolute structure parameter: 0.00 (3) |
0 restraints |
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.02342 (8) | 0.9375 | 0.14451 (6) | 0.0283 (4) | |
N1 | 0.7251 (3) | 0.9419 (9) | 0.8927 (2) | 0.0243 (7) | |
H1A | 0.8062 | 1.0570 | 0.8820 | 0.029* | |
H1B | 0.7834 | 0.7940 | 0.8831 | 0.029* | |
H1C | 0.6668 | 0.9467 | 0.9599 | 0.029* | |
C1 | 0.5705 (4) | 0.9710 (9) | 0.8019 (3) | 0.0220 (8) | |
H1 | 0.5385 | 1.1642 | 0.7926 | 0.026* | |
C1' | 0.4228 (4) | 0.8108 (9) | 0.8536 (3) | 0.0221 (7) | |
O1' | 0.4478 (3) | 0.5815 (7) | 0.8956 (2) | 0.0288 (7) | |
N2 | 0.2716 (3) | 0.9408 (11) | 0.8498 (3) | 0.0350 (8) | |
H2NA | 0.1645 | 0.8615 | 0.8674 | 0.042* | |
H2NB | 0.2575 | 1.0924 | 0.7986 | 0.042* | |
C2 | 0.6081 (4) | 0.8499 (10) | 0.6755 (2) | 0.0278 (9) | |
H2A | 0.6518 | 0.6652 | 0.6872 | 0.033* | |
H2B | 0.5011 | 0.8405 | 0.6231 | 0.033* | |
C3 | 0.7399 (5) | 1.0201 (9) | 0.6108 (3) | 0.0356 (10) | |
H3A | 0.6971 | 1.2058 | 0.6009 | 0.043* | |
H3B | 0.8474 | 1.0264 | 0.6627 | 0.043* | |
C4 | 0.7760 (4) | 0.9076 (12) | 0.4850 (3) | 0.0299 (10) | |
O5 | 0.7516 (5) | 0.6670 (9) | 0.4566 (3) | 0.0523 (10) | |
N6 | 0.8393 (4) | 1.0866 (9) | 0.4092 (3) | 0.0364 (9) | |
H6A | 0.8683 | 0.9894 | 0.3362 | 0.044* | |
H6B | 0.8974 | 1.2451 | 0.4575 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0253 (5) | 0.0304 (6) | 0.0297 (5) | 0.0029 (4) | 0.0045 (3) | 0.0013 (4) |
N1 | 0.0216 (12) | 0.0287 (16) | 0.0231 (11) | −0.0025 (17) | 0.0051 (9) | −0.0046 (17) |
C1 | 0.0243 (14) | 0.019 (2) | 0.0230 (13) | −0.0006 (16) | 0.0041 (11) | 0.0000 (16) |
C1' | 0.0242 (15) | 0.0258 (19) | 0.0167 (12) | −0.0013 (16) | 0.0032 (9) | −0.0008 (15) |
O1' | 0.0280 (13) | 0.0277 (16) | 0.0317 (13) | −0.0003 (12) | 0.0077 (10) | 0.0078 (12) |
N2 | 0.0228 (13) | 0.039 (2) | 0.0438 (16) | 0.0054 (19) | 0.0035 (11) | 0.010 (2) |
C2 | 0.0284 (16) | 0.035 (2) | 0.0206 (15) | −0.0079 (15) | 0.0061 (12) | −0.0004 (17) |
C3 | 0.048 (2) | 0.036 (3) | 0.0244 (15) | −0.0107 (19) | 0.0146 (14) | −0.0065 (17) |
C4 | 0.0291 (16) | 0.038 (3) | 0.0229 (17) | −0.0002 (17) | 0.0018 (12) | −0.006 (2) |
O5 | 0.079 (2) | 0.038 (2) | 0.0423 (16) | −0.0132 (19) | 0.0202 (15) | −0.0157 (17) |
N6 | 0.0504 (19) | 0.037 (2) | 0.0235 (14) | −0.0023 (19) | 0.0151 (13) | −0.0014 (16) |
N1—C1 | 1.499 (4) | C2—C3 | 1.526 (5) |
C1—C1' | 1.525 (5) | C3—C4 | 1.512 (5) |
C1—C2 | 1.538 (4) | C4—O5 | 1.227 (8) |
C1'—O1' | 1.220 (5) | C4—N6 | 1.317 (6) |
C1'—N2 | 1.330 (5) | ||
N1—C1—C1' | 107.2 (3) | C3—C2—C1 | 112.0 (3) |
N1—C1—C2 | 110.6 (3) | C4—C3—C2 | 112.8 (3) |
C1'—C1—C2 | 108.9 (3) | O5—C4—N6 | 122.6 (4) |
O1'—C1'—N2 | 124.5 (4) | O5—C4—C3 | 122.6 (4) |
O1'—C1'—C1 | 120.4 (3) | N6—C4—C3 | 114.8 (4) |
N2—C1'—C1 | 115.1 (4) |
C6H19N5O22+·2Cl− | Dx = 1.358 Mg m−3 Dm = 1.366 (5) Mg m−3 Dm measured by measured |
Mr = 264.16 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 7.536 (3) Å | θ = 0.3–67.6° |
b = 32.487 (3) Å | µ = 4.49 mm−1 |
c = 5.277 (4) Å | T = 293 K |
V = 1291.9 (10) Å3 | Plate, colourless |
Z = 4 | 0.5 × 0.25 × 0.1 mm |
F(000) = 560 |
Rigaku AFC5R diffractometer | 1325 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 67.6° |
ω–2θ scans | h = −8→0 |
Absorption correction: ψ-scan North, et al., 1990 | k = 0→38 |
Tmin = 0.288, Tmax = 0.998 | l = 0→6 |
1364 measured reflections | 3 standard reflections every 100 reflections |
1364 independent reflections | intensity decay: 2% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.055 | Calculated w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.172 | (Δ/σ)max = 0.177 |
S = 1.64 | Δρmax = 0.47 e Å−3 |
1364 reflections | Δρmin = −0.35 e Å−3 |
137 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.016 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.03 (4) |
C6H19N5O22+·2Cl− | V = 1291.9 (10) Å3 |
Mr = 264.16 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.536 (3) Å | µ = 4.49 mm−1 |
b = 32.487 (3) Å | T = 293 K |
c = 5.277 (4) Å | 0.5 × 0.25 × 0.1 mm |
Rigaku AFC5R diffractometer | 1325 reflections with I > 2σ(I) |
Absorption correction: ψ-scan North, et al., 1990 | Rint = 0.000 |
Tmin = 0.288, Tmax = 0.998 | 3 standard reflections every 100 reflections |
1364 measured reflections | intensity decay: 2% |
1364 independent reflections |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.172 | (Δ/σ)max = 0.177 |
S = 1.64 | Δρmax = 0.47 e Å−3 |
1364 reflections | Δρmin = −0.35 e Å−3 |
137 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
0 restraints | Absolute structure parameter: 0.03 (4) |
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.0000 (5) | 0.96691 (8) | 1.2482 (7) | 0.0351 (8) | |
H1A | −0.0684 | 0.9593 | 1.0964 | 0.042* | |
H1B | −0.0697 | 0.9606 | 1.3736 | 0.042* | |
H1C | 0.0474 | 0.9925 | 1.2397 | 0.042* | |
C1 | 0.1574 (5) | 0.94187 (11) | 1.3143 (7) | 0.0331 (9) | |
H1 | 0.2080 | 0.9531 | 1.4708 | 0.040* | |
C1' | 0.2943 (6) | 0.94782 (10) | 1.1029 (8) | 0.0349 (9) | |
O1' | 0.2594 (4) | 0.96764 (8) | 0.9123 (6) | 0.0392 (7) | |
N2 | 0.4494 (6) | 0.93005 (15) | 1.1393 (11) | 0.0712 (15) | |
H2NA | 0.4579 | 0.9141 | 1.2427 | 0.085* | |
H2NB | 0.5158 | 0.9335 | 0.9729 | 0.085* | |
C2 | 0.1111 (5) | 0.89690 (10) | 1.3626 (9) | 0.0332 (9) | |
H2A | 0.2156 | 0.8831 | 1.4285 | 0.040* | |
H2B | 0.0205 | 0.8958 | 1.4931 | 0.040* | |
C3 | 0.0450 (6) | 0.87301 (10) | 1.1332 (9) | 0.0395 (10) | |
H3A | −0.0671 | 0.8844 | 1.0762 | 0.047* | |
H3B | 0.1299 | 0.8754 | 0.9958 | 0.047* | |
C4 | 0.0210 (6) | 0.82801 (10) | 1.2035 (10) | 0.0415 (10) | |
H4A | 0.1328 | 0.8173 | 1.2663 | 0.050* | |
H4B | −0.0654 | 0.8259 | 1.3391 | 0.050* | |
N5 | −0.0375 (5) | 0.80304 (9) | 0.9913 (9) | 0.0431 (10) | |
H5 | 0.0478 | 0.7975 | 0.8457 | 0.052* | |
C6 | −0.2067 (6) | 0.79688 (11) | 0.9338 (9) | 0.0373 (9) | |
N7 | −0.3361 (4) | 0.81292 (11) | 1.0647 (8) | 0.0457 (10) | |
H7A | −0.4350 | 0.8072 | 0.9911 | 0.055* | |
H7B | −0.3325 | 0.8257 | 1.1828 | 0.055* | |
N8 | −0.2479 (6) | 0.77385 (12) | 0.7298 (8) | 0.0523 (10) | |
H8A | −0.1676 | 0.7513 | 0.7092 | 0.063* | |
H8B | −0.3884 | 0.7729 | 0.6931 | 0.063* | |
O1W | 0.5968 (6) | 0.86819 (10) | 0.4949 (8) | 0.0607 (10) | |
Cl1 | 0.76135 (13) | 0.94887 (3) | 0.7367 (2) | 0.0422 (4) | |
Cl2 | 0.33399 (13) | 0.79542 (3) | 0.6922 (2) | 0.0489 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0408 (16) | 0.0297 (13) | 0.0348 (16) | −0.0004 (13) | 0.0078 (17) | 0.0006 (13) |
C1 | 0.039 (2) | 0.0278 (15) | 0.0327 (19) | −0.0059 (14) | 0.003 (2) | −0.0005 (15) |
C1' | 0.043 (2) | 0.0257 (16) | 0.0355 (18) | −0.0027 (15) | 0.002 (2) | 0.0049 (16) |
O1' | 0.0432 (15) | 0.0398 (13) | 0.0345 (15) | −0.0041 (11) | 0.0059 (14) | 0.0063 (12) |
N1' | 0.047 (2) | 0.096 (3) | 0.071 (3) | 0.017 (2) | 0.018 (2) | 0.051 (3) |
C2 | 0.0386 (19) | 0.0278 (16) | 0.0332 (19) | −0.0041 (16) | 0.0033 (17) | 0.0070 (15) |
C3 | 0.048 (2) | 0.0272 (17) | 0.044 (2) | −0.0015 (16) | −0.002 (2) | 0.0035 (17) |
C4 | 0.0404 (18) | 0.0282 (17) | 0.056 (3) | −0.0023 (15) | −0.008 (2) | 0.0043 (18) |
N5 | 0.0379 (17) | 0.0293 (15) | 0.062 (2) | −0.0024 (12) | −0.004 (2) | −0.0052 (17) |
C6 | 0.044 (2) | 0.0235 (15) | 0.044 (2) | −0.0010 (16) | −0.003 (2) | −0.0013 (16) |
N7 | 0.0373 (17) | 0.055 (2) | 0.045 (2) | 0.0019 (16) | −0.002 (2) | −0.0170 (19) |
N8 | 0.063 (2) | 0.0407 (18) | 0.053 (2) | 0.0025 (17) | −0.006 (3) | −0.0142 (17) |
O1W | 0.080 (2) | 0.0467 (15) | 0.055 (2) | −0.0018 (16) | 0.002 (2) | −0.0040 (17) |
Cl1 | 0.0431 (6) | 0.0423 (6) | 0.0412 (6) | 0.0008 (4) | 0.0088 (5) | 0.0000 (4) |
Cl2 | 0.0408 (6) | 0.0501 (6) | 0.0557 (8) | −0.0022 (4) | −0.0074 (5) | −0.0077 (5) |
N1—C1 | 1.480 (5) | C3—C4 | 1.519 (5) |
C1—C2 | 1.524 (4) | C4—N5 | 1.451 (6) |
C1—C1' | 1.532 (6) | N5—C6 | 1.326 (6) |
C1'—O1' | 1.222 (5) | C6—N7 | 1.304 (6) |
C1'—N2 | 1.317 (6) | C6—N8 | 1.347 (6) |
C2—C3 | 1.522 (6) | ||
N1—C1—C2 | 112.5 (3) | C4—C3—C2 | 109.6 (4) |
N1—C1—C1' | 107.4 (3) | N5—C4—C3 | 112.7 (4) |
C2—C1—C1' | 113.4 (3) | C6—N5—C4 | 123.6 (4) |
O1'—C1'—N2 | 122.8 (4) | N7—C6—N5 | 122.5 (4) |
O1'—C1'—C1 | 121.4 (4) | N7—C6—N8 | 118.3 (4) |
N2—C1'—C1 | 115.8 (4) | N5—C6—N8 | 119.2 (4) |
C3—C2—C1 | 115.5 (3) |
Experimental details
(ileNH2) | (valNH2) | (thrNH2) | (serNH2) | |
Crystal data | ||||
Chemical formula | C6H15N2O+·Cl− | C5H13N2O+·Cl− | C4H11N2O2+·Cl− | C3H9N2O2+·Cl− |
Mr | 166.65 | 152.62 | 154.60 | 140.57 |
Crystal system, space group | Monoclinic, P21 | Monoclinic, P21 | Orthorhombic, P212121 | Monoclinic, P21 |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 7.5775 (13), 4.8971 (13), 12.5686 (14) | 5.3377 (8), 7.4572 (9), 9.899 (1) | 10.1624 (15), 10.5673 (17), 6.749 (3) | 7.562 (2), 4.9986 (18), 8.519 (3) |
α, β, γ (°) | 90, 94.195 (12), 90 | 90, 91.73 (1), 90 | 90, 90, 90 | 90, 90.76 (3), 90 |
V (Å3) | 465.14 (16) | 393.84 (9) | 724.8 (3) | 322.00 (18) |
Z | 2 | 2 | 4 | 2 |
Radiation type | Cu Kα | Cu Kα | Cu Kα | Cu Kα |
µ (mm−1) | 3.20 | 3.73 | 4.17 | 4.64 |
Crystal size (mm) | 0.6 × 0.4 × 0.05 | 0.8 × 0.6 × 0.3 | 0.8 × 0.6 × 0.6 | 0.8 × 0.2 × 0.05 |
Data collection | ||||
Diffractometer | Rigaku AFC5R diffractometer | Rigaku AFC5R diffractometer | Rigaku AFC5R diffractometer | Rigaku AFC5R diffractometer |
Absorption correction | ψ-scan North, et al., 1990 | – | ψ-scan North, et al., 1990 | ψ-scan North, et al., 1990 |
Tmin, Tmax | 0.629, 0.999 | – | 0.782, 0.999 | 0.464, 0.793 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 963, 893, 817 | 1458, 731, 718 | 710, 710, 710 | 687, 638, 626 |
Rint | 0.052 | 0.135 | 0.000 | 0.050 |
(sin θ/λ)max (Å−1) | 0.588 | 0.588 | 0.578 | 0.599 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.187, 1.66 | 0.037, 0.097, 0.75 | 0.047, 0.121, 1.10 | 0.050, 0.162, 1.58 |
No. of reflections | 893 | 731 | 710 | 638 |
No. of parameters | 90 | 82 | 83 | 73 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
(Δ/σ)max | 0.094 | 0.176 | 0.049 | 0.003 |
Δρmax, Δρmin (e Å−3) | 0.70, −0.29 | 0.30, −0.41 | 0.50, −0.59 | 0.42, −0.50 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −0.04 (5) | 0.009 (16) | 0.06 (3) | −0.01 (4) |
(metNH2) | (trpNH2) | (glnNH2) | (argNH2) | |
Crystal data | ||||
Chemical formula | C5H13N2OS+·Cl− | C11H14ClN3O | C5H12N3O2+·Cl− | C6H19N5O22+·2Cl− |
Mr | 184.68 | 239.70 | 181.63 | 264.16 |
Crystal system, space group | Monoclinic, P21 | Monoclinic, P21 | Monoclinic, P21 | Orthorhombic, P212121 |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 7.591 (3), 5.029 (3), 11.786 (4) | 7.6394 (11), 5.2786 (13), 14.5967 (14) | 7.741 (2), 4.8907 (13), 10.8159 (10) | 7.536 (3), 32.487 (3), 5.277 (4) |
α, β, γ (°) | 90, 96.49 (3), 90 | 90, 100.047 (10), 90 | 90, 94.180 (13), 90 | 90, 90, 90 |
V (Å3) | 447.0 (4) | 579.59 (17) | 408.39 (16) | 1291.9 (10) |
Z | 2 | 2 | 2 | 4 |
Radiation type | Cu Kα | Cu Kα | Cu Kα | Cu Kα |
µ (mm−1) | 5.51 | 2.78 | 3.83 | 4.49 |
Crystal size (mm) | 0.7 × 0.2 × 0.05 | 0.5 × 0.2 × 0.2 | 0.8 × 0.2 × 0.2 | 0.5 × 0.25 × 0.1 |
Data collection | ||||
Diffractometer | Rigaku AFC5R diffractometer | Rigaku AFC5R diffractometer | Rigaku AFC5R diffractometer | Rigaku AFC5R diffractometer |
Absorption correction | ψ-scan (North, et al., 1990) | ψ-scan North, et al., 1990 | ψ-scan North, et al., 1990 | ψ-scan North, et al., 1990 |
Tmin, Tmax | 0.697, 0.759 | 0.329, 0.573 | 0.355, 0.465 | 0.288, 0.998 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 907, 864, 811 | 1188, 1100, 1075 | 877, 816, 812 | 1364, 1364, 1325 |
Rint | 0.023 | 0.038 | 0.065 | 0.000 |
(sin θ/λ)max (Å−1) | 0.599 | 0.588 | 0.600 | 0.600 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.163, 1.44 | 0.030, 0.095, 0.91 | 0.043, 0.137, 1.39 | 0.055, 0.172, 1.64 |
No. of reflections | 864 | 1100 | 816 | 1364 |
No. of parameters | 90 | 145 | 100 | 137 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
(Δ/σ)max | 0.249 | 0.002 | 0.091 | 0.177 |
Δρmax, Δρmin (e Å−3) | 0.57, −0.52 | 0.31, −0.19 | 0.66, −0.39 | 0.47, −0.35 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.01 (5) | 0.008 (17) | 0.00 (3) | 0.03 (4) |
Computer programs: MSC/AFC (Molecular Structure Corp. 1991), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).