Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013183/fp3042sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013183/fp3042Isup2.hkl | |
Chemdraw file https://doi.org/10.1107/S2053229617013183/fp3042Isup3.cdx |
CCDC reference: 1567310
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015)and ShelXle (Hübschle et al., 2011); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009), enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010).
C7H7O+·Cl− | F(000) = 148 |
Mr = 142.58 | Dx = 1.392 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 9915 reflections |
a = 4.8622 (3) Å | θ = 2.9–36.4° |
b = 6.9718 (4) Å | µ = 0.47 mm−1 |
c = 10.1539 (5) Å | T = 123 K |
β = 98.727 (3)° | Needle, colourless |
V = 340.22 (3) Å3 | 0.41 × 0.15 × 0.11 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 1690 independent reflections |
Radiation source: rotating anode FR591 | 1682 reflections with I > 2σ(I) |
MONTEL optic monochromator | Rint = 0.031 |
Detector resolution: 16 pixels mm-1 | θmax = 28.3°, θmin = 2.9° |
phi– and ω–rotation scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | k = −9→9 |
Tmin = 0.698, Tmax = 0.747 | l = −13→13 |
14261 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.021 | W = 1/[Σ2(FO2) + (0.0407P)2 + 0.0399P] WHERE P = (FO2 + 2FC2)/3 |
wR(F2) = 0.059 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.34 e Å−3 |
1690 reflections | Δρmin = −0.15 e Å−3 |
86 parameters | Absolute structure: Flack (1983) and Parsons et al. (2013) |
2 restraints | Absolute structure parameter: 0.097 (14) |
Experimental. Diffractometer operator C Jandl scanspeed 10 s per frame dx 35 mm 4600 frames measured in 17 data sets phi-scans with delta_phi = 0.5 omega-scans with delta_omega = 0.5 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.83894 (12) | 1.00722 (6) | 0.32306 (7) | 0.0269 (1) | |
O1 | 0.7122 (3) | 0.61466 (18) | 0.37565 (14) | 0.0242 (3) | |
C1 | 0.5421 (3) | 0.5794 (3) | 0.46254 (16) | 0.0191 (5) | |
C2 | 0.4481 (3) | 0.7335 (2) | 0.53459 (17) | 0.0222 (5) | |
C3 | 0.2685 (4) | 0.7279 (3) | 0.62647 (18) | 0.0240 (5) | |
C4 | 0.1276 (3) | 0.5721 (3) | 0.67384 (16) | 0.0227 (5) | |
C5 | 0.1451 (3) | 0.3822 (3) | 0.64158 (19) | 0.0242 (5) | |
C6 | 0.3053 (4) | 0.2993 (2) | 0.5518 (2) | 0.0249 (5) | |
C7 | 0.4782 (4) | 0.3835 (3) | 0.47408 (18) | 0.0223 (5) | |
H1 | 0.751 (6) | 0.738 (5) | 0.370 (4) | 0.063 (9)* | |
H2 | 0.51830 | 0.85660 | 0.51710 | 0.0270* | |
H3 | 0.23370 | 0.84860 | 0.66420 | 0.0290* | |
H4 | 0.00560 | 0.60230 | 0.73560 | 0.0270* | |
H5 | 0.03630 | 0.29610 | 0.68480 | 0.0290* | |
H6 | 0.29120 | 0.16370 | 0.54410 | 0.0300* | |
H7 | 0.56700 | 0.29840 | 0.42070 | 0.0270* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0336 (2) | 0.0171 (2) | 0.0342 (2) | −0.0003 (2) | 0.0185 (2) | 0.0018 (1) |
O1 | 0.0303 (6) | 0.0195 (6) | 0.0269 (6) | −0.0020 (5) | 0.0176 (5) | −0.0018 (4) |
C1 | 0.0205 (7) | 0.0179 (10) | 0.0194 (7) | −0.0008 (6) | 0.0044 (6) | 0.0000 (6) |
C2 | 0.0275 (9) | 0.0141 (7) | 0.0280 (8) | −0.0004 (6) | 0.0137 (7) | −0.0016 (6) |
C3 | 0.0290 (9) | 0.0191 (8) | 0.0264 (9) | 0.0029 (6) | 0.0122 (7) | −0.0038 (6) |
C4 | 0.0203 (8) | 0.0294 (12) | 0.0205 (8) | 0.0009 (7) | 0.0097 (6) | 0.0022 (7) |
C5 | 0.0230 (8) | 0.0251 (9) | 0.0257 (8) | −0.0050 (7) | 0.0078 (7) | 0.0063 (8) |
C6 | 0.0294 (9) | 0.0163 (7) | 0.0299 (10) | −0.0025 (7) | 0.0079 (7) | 0.0016 (6) |
C7 | 0.0275 (8) | 0.0159 (8) | 0.0248 (8) | −0.0003 (7) | 0.0084 (7) | −0.0015 (6) |
O1—C1 | 1.321 (2) | C6—C7 | 1.370 (3) |
O1—H1 | 0.88 (3) | C2—H2 | 0.9500 |
C1—C7 | 1.410 (3) | C3—H3 | 0.9500 |
C1—C2 | 1.414 (2) | C4—H4 | 0.9500 |
C2—C3 | 1.372 (2) | C5—H5 | 0.9500 |
C3—C4 | 1.407 (3) | C6—H6 | 0.9500 |
C4—C5 | 1.370 (3) | C7—H7 | 0.9500 |
C5—C6 | 1.410 (3) | ||
C1—O1—H1 | 113 (2) | C3—C2—H2 | 116.00 |
O1—C1—C2 | 119.24 (17) | C2—C3—H3 | 115.00 |
O1—C1—C7 | 113.84 (16) | C4—C3—H3 | 115.00 |
C2—C1—C7 | 126.91 (15) | C3—C4—H4 | 116.00 |
C1—C2—C3 | 128.26 (15) | C5—C4—H4 | 116.00 |
C2—C3—C4 | 130.36 (18) | C4—C5—H5 | 116.00 |
C3—C4—C5 | 127.82 (16) | C6—C5—H5 | 116.00 |
C4—C5—C6 | 127.70 (16) | C5—C6—H6 | 115.00 |
C5—C6—C7 | 130.14 (16) | C7—C6—H6 | 115.00 |
C1—C7—C6 | 128.73 (17) | C1—C7—H7 | 116.00 |
C1—C2—H2 | 116.00 | C6—C7—H7 | 116.00 |
O1—C1—C2—C3 | 178.61 (17) | C2—C3—C4—C5 | 2.6 (3) |
C7—C1—C2—C3 | −2.7 (3) | C3—C4—C5—C6 | −1.1 (3) |
O1—C1—C7—C6 | −178.33 (19) | C4—C5—C6—C7 | −0.8 (3) |
C2—C1—C7—C6 | 2.9 (3) | C5—C6—C7—C1 | −0.3 (4) |
C1—C2—C3—C4 | −0.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cl1 | 0.88 (3) | 2.00 (3) | 2.8732 (14) | 170 (4) |
C2—H2···Cl1 | 0.95 | 2.89 | 3.620 (2) | 135 |
C3—H3···Cl1i | 0.95 | 2.87 | 3.609 (2) | 135 |
C4—H4···O1ii | 0.95 | 2.64 | 3.351 (2) | 132 |
C5—H5···Cl1ii | 0.95 | 2.79 | 3.717 (2) | 166 |
C7—H7···Cl1iii | 0.95 | 2.69 | 3.623 (2) | 166 |
Symmetry codes: (i) x−1, −y+2, z+1/2; (ii) x−1, −y+1, z+1/2; (iii) x, y−1, z. |