Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019008/lh6450sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019008/lh6450Isup2.hkl |
CCDC reference: 277726
Data collection: Picker Manual (Picker, 1967); cell refinement: Picker Manual; data reduction: DATRDN (Stewart, 1976); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C9H12ClN2O+·Cl− | Z = 4 |
Mr = 235.11 | F(000) = 488 |
Triclinic, P1 | Dx = 1.363 Mg m−3 |
a = 6.726 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 6.837 (2) Å | Cell parameters from 32 reflections |
c = 25.267 (5) Å | θ = 19–37° |
α = 83.57 (2)° | µ = 4.87 mm−1 |
β = 83.03 (2)° | T = 294 K |
γ = 88.03 (2)° | Prism, colorless |
V = 1145.8 (5) Å3 | 0.29 × 0.17 × 0.15 mm |
Picker FACS-1 four-circle diffractometer | 1613 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Ni filtered radiation monochromator | θmax = 65.0°, θmin = 1.8° |
ω/2θ scans | h = 0→7 |
Absorption correction: ψ scan (North et al., 1968) | k = −8→8 |
Tmin = 0.423, Tmax = 0.480 | l = −29→29 |
2628 measured reflections | 3 standard reflections every 100 reflections |
2386 independent reflections | intensity decay: 3.9% |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.206 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0929P)2 + 2.1584P] where P = (Fo2 + 2Fc2)/3 |
2386 reflections | (Δ/σ)max < 0.001 |
257 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
Experimental. Generally no observable reflections above θ = 55° due to poor quality and small size of the crystal and high anisotropic thermal displacement parameters. A number of visible reflections from the region θ = 55–65° were identified from a previous data set collected on a larger but much poorer quality crystal and duly collected. These measures were exercised to prolong the life of our only copper X-ray tube for the Picker diffractometer. There were no other plausible reasons for the checkCIF red A alerts beyond the above. |
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 | ||
Cl2A | 0.2515 (4) | 1.0501 (3) | 0.44186 (9) | 0.0558 (8) | |
Cl1A | 0.7836 (6) | 0.4496 (5) | 0.04422 (12) | 0.1192 (13) | |
C2A | 0.6343 (19) | 0.4776 (15) | 0.1027 (5) | 0.069 (3) | |
C3A | 0.433 (2) | 0.5181 (15) | 0.1017 (4) | 0.079 (3) | |
H3A | 0.3784 | 0.5298 | 0.0693 | 0.077 (7)* | |
C4A | 0.3109 (15) | 0.5411 (15) | 0.1490 (4) | 0.066 (3) | |
H4A | 0.1746 | 0.5677 | 0.1483 | 0.077 (7)* | |
C5A | 0.3912 (16) | 0.5248 (12) | 0.1968 (4) | 0.047 (3) | |
C6A | 0.5887 (18) | 0.4833 (14) | 0.1986 (4) | 0.060 (3) | |
H6A | 0.6429 | 0.4715 | 0.2310 | 0.077 (7)* | |
C7A | 0.7092 (16) | 0.4585 (14) | 0.1506 (5) | 0.070 (3) | |
H7A | 0.8446 | 0.4280 | 0.1515 | 0.077 (7)* | |
C8A | 0.2567 (18) | 0.5495 (14) | 0.2468 (5) | 0.052 (3) | |
O9A | 0.0859 (11) | 0.4764 (9) | 0.2567 (3) | 0.076 (2) | |
N10A | 0.3271 (12) | 0.6529 (11) | 0.2823 (4) | 0.054 (3) | |
H10A | 0.4434 | 0.7037 | 0.2738 | 0.077 (7)* | |
C11A | 0.2214 (14) | 0.6843 (12) | 0.3338 (4) | 0.048 (3) | |
H11A | 0.0808 | 0.6559 | 0.3343 | 0.060 (7)* | |
H11B | 0.2314 | 0.8210 | 0.3399 | 0.060 (7)* | |
C12A | 0.3083 (14) | 0.5537 (13) | 0.3773 (4) | 0.054 (3) | |
H12A | 0.2886 | 0.4173 | 0.3724 | 0.060 (7)* | |
H12B | 0.4514 | 0.5742 | 0.3743 | 0.060 (7)* | |
N13A | 0.2173 (11) | 0.5906 (10) | 0.4318 (3) | 0.059 (2) | |
H13A | 0.2336 | 0.7159 | 0.4365 | 0.077 (7)* | |
H13B | 0.2766 | 0.5128 | 0.4562 | 0.077 (7)* | |
H13C | 0.0872 | 0.5652 | 0.4355 | 0.077 (7)* | |
Cl2B | −0.2498 (4) | 0.5455 (3) | 0.44286 (9) | 0.0577 (8) | |
Cl1B | 0.2670 (8) | 0.0090 (6) | 0.03904 (15) | 0.1515 (18) | |
C2B | 0.128 (3) | 0.0053 (18) | 0.1026 (5) | 0.083 (4) | |
C3B | −0.063 (3) | −0.0490 (16) | 0.1084 (5) | 0.092 (5) | |
H3B | −0.1237 | −0.0830 | 0.0795 | 0.077 (7)* | |
C4B | −0.1671 (18) | −0.0521 (14) | 0.1587 (4) | 0.074 (3) | |
H4B | −0.2994 | −0.0921 | 0.1634 | 0.077 (7)* | |
C5B | −0.0872 (19) | 0.0006 (14) | 0.2033 (5) | 0.057 (3) | |
C6B | 0.1142 (17) | 0.0489 (12) | 0.1937 (4) | 0.059 (3) | |
H6B | 0.1772 | 0.0807 | 0.2223 | 0.077 (7)* | |
C7B | 0.2276 (17) | 0.0523 (14) | 0.1432 (4) | 0.074 (3) | |
H7B | 0.3623 | 0.0846 | 0.1378 | 0.077 (7)* | |
C8B | −0.2082 (19) | 0.0094 (17) | 0.2554 (5) | 0.054 (3) | |
O9B | −0.3527 (11) | −0.0968 (12) | 0.2687 (3) | 0.093 (3) | |
N10B | −0.1594 (12) | 0.1447 (10) | 0.2848 (3) | 0.048 (2) | |
H10B | −0.0594 | 0.2185 | 0.2727 | 0.077 (7)* | |
C11B | −0.2678 (15) | 0.1735 (13) | 0.3367 (4) | 0.050 (3) | |
H11C | −0.4081 | 0.1457 | 0.3365 | 0.060 (7)* | |
H11D | −0.2586 | 0.3099 | 0.3431 | 0.060 (7)* | |
C12B | −0.1873 (14) | 0.0448 (13) | 0.3804 (4) | 0.050 (3) | |
H12C | −0.2103 | −0.0915 | 0.3759 | 0.060 (7)* | |
H12D | −0.0438 | 0.0617 | 0.3778 | 0.060 (7)* | |
N13B | −0.2789 (10) | 0.0866 (10) | 0.4336 (3) | 0.055 (2) | |
H13D | −0.2606 | 0.2121 | 0.4376 | 0.077 (7)* | |
H13E | −0.2222 | 0.0094 | 0.4586 | 0.077 (7)* | |
H13F | −0.4095 | 0.0636 | 0.4370 | 0.077 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl2A | 0.056 (2) | 0.0603 (17) | 0.0518 (19) | −0.0029 (14) | −0.0106 (15) | −0.0043 (12) |
Cl1A | 0.157 (3) | 0.121 (3) | 0.065 (2) | 0.007 (2) | 0.048 (2) | −0.0162 (17) |
C2A | 0.078 (9) | 0.051 (6) | 0.070 (9) | −0.005 (5) | 0.010 (7) | 0.006 (5) |
C3A | 0.122 (10) | 0.077 (8) | 0.042 (6) | 0.009 (7) | −0.010 (6) | −0.016 (5) |
C4A | 0.056 (6) | 0.091 (8) | 0.055 (6) | 0.004 (5) | −0.011 (5) | −0.020 (5) |
C5A | 0.055 (7) | 0.040 (5) | 0.045 (7) | −0.013 (5) | 0.001 (5) | −0.001 (4) |
C6A | 0.071 (8) | 0.065 (6) | 0.042 (6) | 0.006 (5) | −0.005 (5) | 0.003 (4) |
C7A | 0.065 (7) | 0.064 (7) | 0.080 (8) | 0.001 (5) | −0.002 (6) | −0.002 (6) |
C8A | 0.070 (7) | 0.034 (5) | 0.052 (7) | −0.018 (5) | −0.007 (5) | 0.003 (4) |
O9A | 0.066 (5) | 0.074 (4) | 0.090 (5) | −0.031 (4) | 0.017 (4) | −0.027 (3) |
N10A | 0.054 (6) | 0.062 (6) | 0.044 (6) | −0.020 (5) | 0.007 (5) | −0.004 (5) |
C11A | 0.047 (7) | 0.048 (6) | 0.048 (7) | −0.001 (5) | −0.009 (6) | 0.002 (5) |
C12A | 0.059 (8) | 0.055 (7) | 0.046 (7) | 0.004 (6) | −0.005 (6) | −0.004 (5) |
N13A | 0.066 (7) | 0.066 (6) | 0.046 (6) | −0.005 (5) | −0.015 (5) | 0.001 (4) |
Cl2B | 0.056 (2) | 0.0595 (17) | 0.057 (2) | −0.0036 (14) | −0.0103 (15) | −0.0015 (13) |
Cl1B | 0.220 (5) | 0.146 (3) | 0.071 (2) | 0.021 (3) | 0.046 (3) | −0.012 (2) |
C2B | 0.128 (13) | 0.064 (8) | 0.053 (8) | 0.028 (8) | 0.013 (9) | −0.018 (6) |
C3B | 0.152 (14) | 0.067 (8) | 0.060 (8) | 0.002 (8) | −0.029 (9) | 0.002 (6) |
C4B | 0.098 (8) | 0.064 (7) | 0.061 (7) | −0.017 (6) | −0.016 (6) | 0.002 (5) |
C5B | 0.079 (10) | 0.054 (6) | 0.041 (6) | −0.002 (6) | −0.009 (6) | −0.013 (5) |
C6B | 0.062 (7) | 0.045 (5) | 0.066 (7) | 0.001 (5) | 0.007 (5) | −0.010 (4) |
C7B | 0.075 (7) | 0.068 (7) | 0.073 (8) | 0.002 (6) | 0.015 (6) | −0.006 (6) |
C8B | 0.062 (7) | 0.061 (7) | 0.037 (6) | −0.008 (5) | 0.000 (5) | 0.004 (5) |
O9B | 0.084 (6) | 0.093 (6) | 0.103 (6) | −0.052 (5) | 0.019 (4) | −0.029 (4) |
N10B | 0.060 (6) | 0.045 (5) | 0.042 (6) | −0.009 (5) | −0.003 (5) | −0.009 (4) |
C11B | 0.062 (8) | 0.058 (7) | 0.029 (6) | 0.005 (5) | 0.002 (6) | −0.010 (5) |
C12B | 0.057 (8) | 0.059 (7) | 0.035 (6) | 0.009 (6) | −0.013 (6) | −0.006 (5) |
N13B | 0.058 (6) | 0.066 (6) | 0.038 (6) | −0.011 (5) | −0.004 (5) | 0.000 (4) |
Cl1A—C2A | 1.708 (12) | Cl1B—C2B | 1.753 (12) |
C2A—C7A | 1.358 (13) | C2B—C3B | 1.342 (16) |
C2A—C3A | 1.377 (14) | C2B—C7B | 1.363 (15) |
C3A—C4A | 1.385 (12) | C3B—C4B | 1.373 (15) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.375 (12) | C4B—C5B | 1.393 (12) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.354 (11) | C5B—C6B | 1.392 (13) |
C5A—C8A | 1.484 (13) | C5B—C8B | 1.467 (13) |
C6A—C7A | 1.398 (13) | C6B—C7B | 1.404 (12) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—O9A | 1.254 (11) | C8B—O9B | 1.224 (11) |
C8A—N10A | 1.342 (11) | C8B—N10B | 1.322 (11) |
N10A—C11A | 1.438 (10) | N10B—C11B | 1.450 (10) |
N10A—H10A | 0.8600 | N10B—H10B | 0.8600 |
C11A—C12A | 1.500 (10) | C11B—C12B | 1.477 (10) |
C11A—H11A | 0.9700 | C11B—H11C | 0.9700 |
C11A—H11B | 0.9700 | C11B—H11D | 0.9700 |
C12A—N13A | 1.482 (10) | C12B—N13B | 1.464 (9) |
C12A—H12A | 0.9700 | C12B—H12C | 0.9700 |
C12A—H12B | 0.9700 | C12B—H12D | 0.9700 |
N13A—H13A | 0.8900 | N13B—H13D | 0.8900 |
N13A—H13B | 0.8900 | N13B—H13E | 0.8900 |
N13A—H13C | 0.8900 | N13B—H13F | 0.8900 |
C7A—C2A—C3A | 118.8 (11) | C3B—C2B—C7B | 124.6 (13) |
C7A—C2A—Cl1A | 121.5 (10) | C3B—C2B—Cl1B | 118.6 (13) |
C3A—C2A—Cl1A | 119.7 (10) | C7B—C2B—Cl1B | 116.8 (13) |
C2A—C3A—C4A | 120.0 (11) | C2B—C3B—C4B | 117.1 (13) |
C2A—C3A—H3A | 120.0 | C2B—C3B—H3B | 121.5 |
C4A—C3A—H3A | 120.0 | C4B—C3B—H3B | 121.5 |
C5A—C4A—C3A | 120.1 (10) | C3B—C4B—C5B | 124.4 (12) |
C5A—C4A—H4A | 120.0 | C3B—C4B—H4B | 117.8 |
C3A—C4A—H4A | 120.0 | C5B—C4B—H4B | 117.8 |
C6A—C5A—C4A | 120.8 (11) | C4B—C5B—C6B | 114.3 (12) |
C6A—C5A—C8A | 120.4 (10) | C4B—C5B—C8B | 122.4 (12) |
C4A—C5A—C8A | 118.8 (10) | C6B—C5B—C8B | 123.3 (11) |
C5A—C6A—C7A | 118.4 (10) | C5B—C6B—C7B | 123.5 (12) |
C5A—C6A—H6A | 120.8 | C5B—C6B—H6B | 118.2 |
C7A—C6A—H6A | 120.8 | C7B—C6B—H6B | 118.2 |
C2A—C7A—C6A | 121.9 (11) | C2B—C7B—C6B | 116.0 (12) |
C2A—C7A—H7A | 119.0 | C2B—C7B—H7B | 122.0 |
C6A—C7A—H7A | 119.0 | C6B—C7B—H7B | 122.0 |
O9A—C8A—N10A | 120.3 (12) | O9B—C8B—N10B | 122.9 (12) |
O9A—C8A—C5A | 122.9 (11) | O9B—C8B—C5B | 120.6 (12) |
N10A—C8A—C5A | 116.8 (11) | N10B—C8B—C5B | 116.4 (11) |
C8A—N10A—C11A | 124.4 (10) | C8B—N10B—C11B | 122.6 (10) |
C8A—N10A—H10A | 117.8 | C8B—N10B—H10B | 118.7 |
C11A—N10A—H10A | 117.8 | C11B—N10B—H10B | 118.7 |
N10A—C11A—C12A | 110.1 (8) | N10B—C11B—C12B | 111.6 (8) |
N10A—C11A—H11A | 109.6 | N10B—C11B—H11C | 109.3 |
C12A—C11A—H11A | 109.6 | C12B—C11B—H11C | 109.3 |
N10A—C11A—H11B | 109.6 | N10B—C11B—H11D | 109.3 |
C12A—C11A—H11B | 109.6 | C12B—C11B—H11D | 109.3 |
H11A—C11A—H11B | 108.2 | H11C—C11B—H11D | 108.0 |
N13A—C12A—C11A | 112.9 (8) | N13B—C12B—C11B | 112.7 (8) |
N13A—C12A—H12A | 109.0 | N13B—C12B—H12C | 109.1 |
C11A—C12A—H12A | 109.0 | C11B—C12B—H12C | 109.1 |
N13A—C12A—H12B | 109.0 | N13B—C12B—H12D | 109.1 |
C11A—C12A—H12B | 109.0 | C11B—C12B—H12D | 109.1 |
H12A—C12A—H12B | 107.8 | H12C—C12B—H12D | 107.8 |
C12A—N13A—H13A | 109.5 | C12B—N13B—H13D | 109.5 |
C12A—N13A—H13B | 109.5 | C12B—N13B—H13E | 109.5 |
H13A—N13A—H13B | 109.5 | H13D—N13B—H13E | 109.5 |
C12A—N13A—H13C | 109.5 | C12B—N13B—H13F | 109.5 |
H13A—N13A—H13C | 109.5 | H13D—N13B—H13F | 109.5 |
H13B—N13A—H13C | 109.5 | H13E—N13B—H13F | 109.5 |
C6A—C5A—C8A—N10A | 42.3 (12) | C6B—C5B—C8B—N10B | 31.1 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N10A—H10A···O9Bi | 0.86 | 1.95 | 2.762 (11) | 157 |
N10B—H10B···O9A | 0.86 | 2.02 | 2.826 (10) | 155 |
N13A—H13A···Cl2A | 0.89 | 2.31 | 3.198 (7) | 174 |
N13A—H13B···Cl2Bii | 0.89 | 2.52 | 3.231 (8) | 137 |
N13A—H13C···Cl2B | 0.89 | 2.26 | 3.143 (8) | 172 |
N13B—H13D···Cl2B | 0.89 | 2.30 | 3.187 (7) | 173 |
N13B—H13E···Cl2Aii | 0.89 | 2.49 | 3.206 (7) | 138 |
N13B—H13F···Cl2Aiii | 0.89 | 2.27 | 3.157 (7) | 172 |
C12A—H12B···Cl2Biv | 0.97 | 2.80 | 3.569 (10) | 137 |
C12B—H12D···Cl2Av | 0.97 | 2.70 | 3.501 (9) | 140 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z+1; (iii) x−1, y−1, z; (iv) x+1, y, z; (v) x, y−1, z. |