Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005337/nc6023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005337/nc6023Isup2.hkl |
CCDC reference: 269823
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.
C6H12NO2+·Cl− | F(000) = 176 |
Mr = 165.62 | Dx = 1.364 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 8363 reflections |
a = 7.2545 (10) Å | θ = 3.8–25.7° |
b = 7.2018 (9) Å | µ = 0.42 mm−1 |
c = 7.7886 (13) Å | T = 173 K |
β = 97.819 (12)° | Block, colourless |
V = 403.14 (10) Å3 | 0.37 × 0.23 × 0.19 mm |
Z = 2 |
Stoe IPDS-II two-circle diffractometer | 1477 independent reflections |
Radiation source: fine-focus sealed tube | 1460 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans | θmax = 25.5°, θmin = 3.9° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −8→8 |
Tmin = 0.861, Tmax = 0.925 | k = −8→8 |
3354 measured reflections | l = −9→9 |
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)] = 0.022 | w = 1/[σ2(Fo2) + (0.0315P)2 + 0.0946P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.057 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.20 e Å−3 |
1477 reflections | Δρmin = −0.17 e Å−3 |
104 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.075 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 671 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.10 (6) |
Experimental. ; |
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 | −0.19824 (4) | 0.89548 (5) | 0.87208 (4) | 0.01996 (13) | |
C1 | 0.2393 (2) | 0.8196 (2) | 0.41007 (19) | 0.0182 (3) | |
H1 | 0.2663 | 0.6838 | 0.4037 | 0.022* | |
C2 | 0.11341 (19) | 0.8717 (3) | 0.24271 (17) | 0.0193 (3) | |
H2A | −0.0040 | 0.8002 | 0.2340 | 0.023* | |
H2B | 0.0825 | 1.0055 | 0.2441 | 0.023* | |
N3 | 0.21165 (19) | 0.82958 (19) | 0.09018 (17) | 0.0187 (3) | |
H3A | 0.225 (3) | 0.696 (3) | 0.091 (3) | 0.034 (6)* | |
H3B | 0.131 (3) | 0.863 (3) | −0.002 (3) | 0.030 (5)* | |
C4 | 0.3972 (2) | 0.9239 (2) | 0.0966 (2) | 0.0236 (4) | |
H4A | 0.3790 | 1.0600 | 0.0888 | 0.028* | |
H4B | 0.4578 | 0.8838 | −0.0037 | 0.028* | |
C5 | 0.5219 (2) | 0.8764 (3) | 0.26385 (19) | 0.0246 (3) | |
H5A | 0.6395 | 0.9473 | 0.2696 | 0.029* | |
H5B | 0.5528 | 0.7425 | 0.2645 | 0.029* | |
C6 | 0.4268 (2) | 0.9222 (2) | 0.42292 (19) | 0.0216 (4) | |
H6A | 0.4061 | 1.0578 | 0.4289 | 0.026* | |
H6B | 0.5077 | 0.8838 | 0.5297 | 0.026* | |
C7 | 0.1465 (2) | 0.8503 (2) | 0.5709 (2) | 0.0246 (4) | |
O1 | −0.03690 (16) | 0.8621 (2) | 0.53883 (15) | 0.0353 (4) | |
H1O | −0.074 (4) | 0.872 (5) | 0.642 (3) | 0.069 (8)* | |
O2 | 0.2290 (2) | 0.8526 (5) | 0.71339 (17) | 0.0714 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01918 (18) | 0.02398 (19) | 0.01762 (17) | 0.00124 (17) | 0.00571 (11) | 0.00071 (17) |
C1 | 0.0171 (7) | 0.0238 (7) | 0.0137 (7) | 0.0006 (6) | 0.0019 (6) | −0.0003 (6) |
C2 | 0.0170 (6) | 0.0289 (10) | 0.0124 (6) | 0.0022 (7) | 0.0034 (5) | −0.0001 (7) |
N3 | 0.0199 (6) | 0.0248 (7) | 0.0116 (6) | 0.0021 (5) | 0.0028 (5) | 0.0003 (5) |
C4 | 0.0230 (7) | 0.0296 (11) | 0.0197 (7) | −0.0015 (7) | 0.0083 (6) | 0.0038 (7) |
C5 | 0.0167 (6) | 0.0341 (9) | 0.0235 (7) | −0.0028 (8) | 0.0048 (5) | −0.0018 (8) |
C6 | 0.0208 (7) | 0.0258 (10) | 0.0175 (6) | −0.0033 (7) | −0.0001 (5) | −0.0034 (6) |
C7 | 0.0229 (8) | 0.0354 (12) | 0.0159 (7) | −0.0005 (6) | 0.0035 (6) | 0.0001 (6) |
O1 | 0.0221 (6) | 0.0668 (11) | 0.0179 (5) | 0.0079 (6) | 0.0064 (4) | −0.0031 (7) |
O2 | 0.0276 (6) | 0.174 (3) | 0.0125 (5) | 0.0070 (11) | 0.0020 (5) | −0.0038 (10) |
C1—C7 | 1.516 (2) | C4—H4A | 0.9900 |
C1—C2 | 1.5329 (19) | C4—H4B | 0.9900 |
C1—C6 | 1.539 (2) | C5—C6 | 1.534 (2) |
C1—H1 | 1.0000 | C5—H5A | 0.9900 |
C2—N3 | 1.4972 (18) | C5—H5B | 0.9900 |
C2—H2A | 0.9900 | C6—H6A | 0.9900 |
C2—H2B | 0.9900 | C6—H6B | 0.9900 |
N3—C4 | 1.502 (2) | C7—O2 | 1.187 (2) |
N3—H3A | 0.96 (2) | C7—O1 | 1.323 (2) |
N3—H3B | 0.90 (2) | O1—H1O | 0.89 (3) |
C4—C5 | 1.521 (2) | ||
C7—C1—C2 | 112.75 (13) | C5—C4—H4A | 109.5 |
C7—C1—C6 | 111.35 (12) | N3—C4—H4B | 109.5 |
C2—C1—C6 | 110.91 (13) | C5—C4—H4B | 109.5 |
C7—C1—H1 | 107.2 | H4A—C4—H4B | 108.1 |
C2—C1—H1 | 107.2 | C4—C5—C6 | 111.29 (13) |
C6—C1—H1 | 107.2 | C4—C5—H5A | 109.4 |
N3—C2—C1 | 109.41 (12) | C6—C5—H5A | 109.4 |
N3—C2—H2A | 109.8 | C4—C5—H5B | 109.4 |
C1—C2—H2A | 109.8 | C6—C5—H5B | 109.4 |
N3—C2—H2B | 109.8 | H5A—C5—H5B | 108.0 |
C1—C2—H2B | 109.8 | C5—C6—C1 | 109.56 (12) |
H2A—C2—H2B | 108.2 | C5—C6—H6A | 109.8 |
C2—N3—C4 | 113.78 (12) | C1—C6—H6A | 109.8 |
C2—N3—H3A | 104.8 (14) | C5—C6—H6B | 109.8 |
C4—N3—H3A | 111.3 (14) | C1—C6—H6B | 109.8 |
C2—N3—H3B | 104.6 (12) | H6A—C6—H6B | 108.2 |
C4—N3—H3B | 113.1 (13) | O2—C7—O1 | 122.79 (15) |
H3A—N3—H3B | 108.7 (19) | O2—C7—C1 | 123.39 (16) |
N3—C4—C5 | 110.65 (13) | O1—C7—C1 | 113.68 (14) |
N3—C4—H4A | 109.5 | C7—O1—H1O | 104.9 (18) |
C7—C1—C2—N3 | −177.50 (13) | C7—C1—C6—C5 | 176.03 (15) |
C6—C1—C2—N3 | 56.85 (18) | C2—C1—C6—C5 | −57.54 (18) |
C1—C2—N3—C4 | −56.29 (19) | C2—C1—C7—O2 | −165.3 (2) |
C2—N3—C4—C5 | 55.54 (19) | C6—C1—C7—O2 | −39.9 (3) |
N3—C4—C5—C6 | −54.7 (2) | C2—C1—C7—O1 | 18.9 (2) |
C4—C5—C6—C1 | 56.3 (2) | C6—C1—C7—O1 | 144.29 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···Cl1 | 0.89 (3) | 2.11 (3) | 2.9985 (13) | 173 (2) |
N3—H3A···Cl1i | 0.96 (2) | 2.20 (2) | 3.1428 (15) | 166 (2) |
N3—H3B···Cl1ii | 0.90 (2) | 2.47 (2) | 3.2525 (15) | 146.8 (16) |
N3—H3B···O2ii | 0.90 (2) | 2.419 (19) | 2.9590 (19) | 119.0 (15) |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x, y, z−1. |