Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810503747X/av5045sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810503747X/av5045Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810503747X/av5045IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810503747X/av5045IIIsup4.hkl |
CCDC references: 298305; 298306; 298307
For all compounds, data collection: CrysAlis CCD 1.171.23 beta (Oxford Diffraction Poland, 2004); cell refinement: CrysAlis RED 1.171.24 beta (Oxford Diffraction Poland, 2004); data reduction: CrysAlis RED 1.171.24 beta (Oxford Diffraction Poland, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C_{6}H_{6} | The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication |
M_{r} = 78.11 | D_{x} = 1.139 Mg m^{−}^{3} |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 7.243 (3) Å | Cell parameters from 249 reflections |
b = 9.310 (17) Å | θ = 4.7–23.1° |
c = 6.756 (3) Å | µ = 0.06 mm^{−}^{1} |
V = 455.6 (9) Å^{3} | T = 296 K |
Z = 4 | , colourless |
F(000) = 168 | 0.1 mm (radius) |
KM4-CCD diffractometer | 48 independent reflections |
Radiation source: fine-focus sealed tube | 48 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.145 |
Detector resolution: 16.4 pixels mm^{-1} | θ_{max} = 23.1°, θ_{min} = 4.7° |
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168 | h = −7→6 |
Absorption correction: integration Crystal absorption, DAC absorption and gasket shadowing absorption has been applied A. Katrusiak, Z. Kristallogr. 2004, 219, 461-467 | k = −5→6 |
T_{min} = 0.481, T_{max} = 0.919 | l = −6→5 |
293 measured reflections |
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.295 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0508P)^{2} + 19.4433P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 1.30 | (Δ/σ)_{max} < 0.001 |
48 reflections | Δρ_{max} = 0.17 e Å^{−}^{3} |
13 parameters | Δρ_{min} = −0.20 e Å^{−}^{3} |
0 restraints | Extinction correction: SHELXL |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.02 (7) |
C_{6}H_{6} | V = 455.6 (9) Å^{3} |
M_{r} = 78.11 | Z = 4 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 7.243 (3) Å | µ = 0.06 mm^{−}^{1} |
b = 9.310 (17) Å | T = 296 K |
c = 6.756 (3) Å | 0.1 mm (radius) |
KM4-CCD diffractometer | 48 independent reflections |
Absorption correction: integration Crystal absorption, DAC absorption and gasket shadowing absorption has been applied A. Katrusiak, Z. Kristallogr. 2004, 219, 461-467 | 48 reflections with I > 2σ(I) |
T_{min} = 0.481, T_{max} = 0.919 | R_{int} = 0.145 |
293 measured reflections | θ_{max} = 23.1° |
R[F^{2} > 2σ(F^{2})] = 0.132 | 0 restraints |
wR(F^{2}) = 0.295 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.30 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0508P)^{2} + 19.4433P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
48 reflections | Δρ_{max} = 0.17 e Å^{−}^{3} |
13 parameters | Δρ_{min} = −0.20 e Å^{−}^{3} |
Experimental. high-pressure measurement at 0.30 (5) GPa - the high pressure benzene I |
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 F^{2} against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^{2}, conventional R-factors R are based on F, with F set to zero for negative F^{2}. The threshold expression of F^{2} > σ(F^{2}) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^{2} 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 | U_{iso}*/U_{eq} | ||
C1 | −0.052 (4) | 0.146 (7) | 0.019 (5) | 0.030 (11)* | |
H1 | −0.0831 | 0.2424 | 0.0322 | 0.036* | |
C2 | 0.087 (4) | 0.083 (7) | 0.135 (6) | 0.026 (11)* | |
H2 | 0.1456 | 0.1398 | 0.2295 | 0.032* | |
C3 | 0.141 (5) | −0.058 (7) | 0.115 (6) | 0.037 (12)* | |
H3 | 0.2377 | −0.0940 | 0.1911 | 0.045* |
C1—C3^{i} | 1.38 (5) | C2—H2 | 0.9300 |
C1—C2 | 1.40 (4) | C3—C1^{i} | 1.38 (5) |
C1—H1 | 0.9300 | C3—H3 | 0.9300 |
C2—C3 | 1.38 (8) | ||
C3^{i}—C1—C2 | 117 (5) | C3—C2—H2 | 118.4 |
C3^{i}—C1—H1 | 121.4 | C1^{i}—C3—C2 | 120 (4) |
C2—C1—H1 | 121.4 | C1^{i}—C3—H3 | 120.1 |
C1—C2—C3 | 123 (4) | C2—C3—H3 | 120.1 |
C1—C2—H2 | 118.4 | ||
C3^{i}—C1—C2—C3 | 2 (7) | C1—C2—C3—C1^{i} | −2 (7) |
Symmetry code: (i) −x, −y, −z. |
C_{6}H_{6} | The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication |
M_{r} = 78.11 | D_{x} = 1.157 Mg m^{−}^{3} |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 7.287 (6) Å | Cell parameters from 376 reflections |
b = 9.20 (2) Å | θ = 4.7–29.6° |
c = 6.688 (9) Å | µ = 0.07 mm^{−}^{1} |
V = 448.4 (12) Å^{3} | T = 296 K |
Z = 4 | , colourless |
F(000) = 168 | 0.1 mm (radius) |
KM4-CCD diffractometer | 179 independent reflections |
Radiation source: fine-focus sealed tube | 94 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.132 |
Detector resolution: 16.4 pixels mm^{-1} | θ_{max} = 29.6°, θ_{min} = 4.7° |
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168 | h = −9→9 |
Absorption correction: integration Crystal absorption, DAC absorption and gasket shadowing absorption has been applied A. Katrusiak, Z. Kristallogr. 2004, 219, 461-467 | k = −9→8 |
T_{min} = 0.477, T_{max} = 0.865 | l = −7→7 |
1167 measured reflections |
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ^{2}(F_{o}^{2}) + (0.060P)^{2} + 0.030P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
179 reflections | (Δ/σ)_{max} < 0.001 |
37 parameters | Δρ_{max} = 0.11 e Å^{−}^{3} |
0 restraints | Δρ_{min} = −0.09 e Å^{−}^{3} |
C_{6}H_{6} | V = 448.4 (12) Å^{3} |
M_{r} = 78.11 | Z = 4 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 7.287 (6) Å | µ = 0.07 mm^{−}^{1} |
b = 9.20 (2) Å | T = 296 K |
c = 6.688 (9) Å | 0.1 mm (radius) |
KM4-CCD diffractometer | 179 independent reflections |
Absorption correction: integration Crystal absorption, DAC absorption and gasket shadowing absorption has been applied A. Katrusiak, Z. Kristallogr. 2004, 219, 461-467 | 94 reflections with I > 2σ(I) |
T_{min} = 0.477, T_{max} = 0.865 | R_{int} = 0.132 |
1167 measured reflections |
R[F^{2} > 2σ(F^{2})] = 0.053 | 0 restraints |
wR(F^{2}) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρ_{max} = 0.11 e Å^{−}^{3} |
179 reflections | Δρ_{min} = −0.09 e Å^{−}^{3} |
37 parameters |
Experimental. high-pressure measurement at 0.70 (5) GPa - the high pressure of benzene I |
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 F^{2} against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^{2}, conventional R-factors R are based on F, with F set to zero for negative F^{2}. The threshold expression of F^{2} > σ(F^{2}) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^{2} 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 | U_{iso}*/U_{eq} | ||
C1 | −0.0537 (8) | 0.1425 (9) | 0.0097 (12) | 0.037 (2) | |
H1 | −0.085 (6) | 0.246 (7) | 0.034 (8) | 0.044* | |
C2 | 0.0840 (7) | 0.0924 (10) | 0.1373 (10) | 0.040 (2) | |
H2 | 0.140 (6) | 0.156 (6) | 0.219 (8) | 0.048* | |
C3 | 0.1343 (7) | −0.0521 (9) | 0.1235 (12) | 0.044 (2) | |
H3 | 0.220 (6) | −0.080 (6) | 0.204 (9) | 0.052* |
U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} | |
C1 | 0.039 (3) | 0.028 (8) | 0.043 (6) | 0.005 (4) | 0.002 (4) | 0.002 (5) |
C2 | 0.034 (4) | 0.060 (7) | 0.025 (6) | 0.005 (4) | −0.005 (3) | −0.001 (4) |
C3 | 0.043 (4) | 0.048 (7) | 0.039 (6) | 0.002 (5) | −0.007 (4) | 0.006 (5) |
C1—C3^{i} | 1.353 (10) | C2—H2 | 0.90 (5) |
C1—C2 | 1.396 (8) | C3—C1^{i} | 1.353 (10) |
C1—H1 | 0.99 (6) | C3—H3 | 0.86 (5) |
C2—C3 | 1.382 (10) | ||
C3^{i}—C1—C2 | 120.8 (8) | C1—C2—H2 | 119 (4) |
C3^{i}—C1—H1 | 127 (3) | C1^{i}—C3—C2 | 121.4 (7) |
C2—C1—H1 | 113 (3) | C1^{i}—C3—H3 | 123 (4) |
C3—C2—C1 | 117.9 (7) | C2—C3—H3 | 116 (4) |
C3—C2—H2 | 123 (4) | ||
C3^{i}—C1—C2—C3 | −0.2 (10) | C1—C2—C3—C1^{i} | 0.2 (10) |
Symmetry code: (i) −x, −y, −z. |
C_{6}H_{6} | The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication |
M_{r} = 78.11 | D_{x} = 1.205 Mg m^{−}^{3} |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 7.221 (4) Å | Cell parameters from 530 reflections |
b = 9.05 (2) Å | θ = 4.8–29.4° |
c = 6.590 (5) Å | µ = 0.07 mm^{−}^{1} |
V = 430.65 (10) Å^{3} | T = 296 K |
Z = 4 | , colourless |
F(000) = 168 | 0.1 mm (radius) |
KM4-CCD diffractometer | 126 independent reflections |
Radiation source: fine-focus sealed tube | 108 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.151 |
Detector resolution: 16.4 pixels mm^{-1} | θ_{max} = 29.4°, θ_{min} = 4.8° |
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168 | h = −9→9 |
Absorption correction: integration Crystal absorption, DAC absorption and gasket shadowing absorption has been applied A. Katrusiak, Z. Kristallogr. 2004, 219, 461-467 | k = −5→5 |
T_{min} = 0.479, T_{max} = 0.850 | l = −8→8 |
1400 measured reflections |
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.142 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.248 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ^{2}(F_{o}^{2}) + (0.P)^{2} + 7.984P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
126 reflections | (Δ/σ)_{max} < 0.001 |
13 parameters | Δρ_{max} = 0.13 e Å^{−}^{3} |
0 restraints | Δρ_{min} = −0.12 e Å^{−}^{3} |
C_{6}H_{6} | V = 430.65 (10) Å^{3} |
M_{r} = 78.11 | Z = 4 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 7.221 (4) Å | µ = 0.07 mm^{−}^{1} |
b = 9.05 (2) Å | T = 296 K |
c = 6.590 (5) Å | 0.1 mm (radius) |
KM4-CCD diffractometer | 126 independent reflections |
Absorption correction: integration Crystal absorption, DAC absorption and gasket shadowing absorption has been applied A. Katrusiak, Z. Kristallogr. 2004, 219, 461-467 | 108 reflections with I > 2σ(I) |
T_{min} = 0.479, T_{max} = 0.850 | R_{int} = 0.151 |
1400 measured reflections |
R[F^{2} > 2σ(F^{2})] = 0.142 | 0 restraints |
wR(F^{2}) = 0.248 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρ_{max} = 0.13 e Å^{−}^{3} |
126 reflections | Δρ_{min} = −0.12 e Å^{−}^{3} |
13 parameters |
Experimental. high-pressure measurement at 1.10 (5) GPa - the high pressure of benzene I |
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 F^{2} against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^{2}, conventional R-factors R are based on F, with F set to zero for negative F^{2}. The threshold expression of F^{2} > σ(F^{2}) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^{2} 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 | U_{iso}*/U_{eq} | ||
C1 | −0.0565 (15) | 0.145 (3) | 0.0049 (19) | 0.040 (4)* | |
H1 | −0.0920 | 0.2438 | 0.0067 | 0.048* | |
C2 | 0.0835 (13) | 0.096 (2) | 0.1399 (15) | 0.021 (3)* | |
H2 | 0.1369 | 0.1585 | 0.2348 | 0.025* | |
C3 | 0.1374 (18) | −0.053 (3) | 0.123 (2) | 0.048 (5)* | |
H3 | 0.2329 | −0.0880 | 0.2049 | 0.057* |
C1—C3^{i} | 1.32 (2) | C2—H2 | 0.9300 |
C1—C2 | 1.419 (16) | C3—C1^{i} | 1.32 (2) |
C1—H1 | 0.9300 | C3—H3 | 0.9300 |
C2—C3 | 1.41 (3) | ||
C3^{i}—C1—C2 | 121 (2) | C3—C2—H2 | 121.6 |
C3^{i}—C1—H1 | 119.4 | C1^{i}—C3—C2 | 122.0 (16) |
C2—C1—H1 | 119.4 | C1^{i}—C3—H3 | 119.0 |
C1—C2—C3 | 116.8 (14) | C2—C3—H3 | 119.0 |
C1—C2—H2 | 121.6 | ||
C3^{i}—C1—C2—C3 | 3 (2) | C1—C2—C3—C1^{i} | −3 (2) |
Symmetry code: (i) −x, −y, −z. |
Experimental details
(I) | (II) | (III) | |
Crystal data | |||
Chemical formula | C_{6}H_{6} | C_{6}H_{6} | C_{6}H_{6} |
M_{r} | 78.11 | 78.11 | 78.11 |
Crystal system, space group | Orthorhombic, Pbca | Orthorhombic, Pbca | Orthorhombic, Pbca |
Temperature (K) | 296 | 296 | 296 |
a, b, c (Å) | 7.243 (3), 9.310 (17), 6.756 (3) | 7.287 (6), 9.20 (2), 6.688 (9) | 7.221 (4), 9.05 (2), 6.590 (5) |
V (Å^{3}) | 455.6 (9) | 448.4 (12) | 430.65 (10) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm^{−}^{1}) | 0.06 | 0.07 | 0.07 |
Crystal size (mm) | 0.1 (radius) | 0.1 (radius) | 0.1 (radius) |
Data collection | |||
Diffractometer | KM4-CCD diffractometer | KM4-CCD diffractometer | KM4-CCD diffractometer |
Absorption correction | Integration Crystal absorption, DAC absorption and gasket shadowing absorption has been applied A. Katrusiak, Z. Kristallogr. 2004, 219, 461-467 | Integration Crystal absorption, DAC absorption and gasket shadowing absorption has been applied A. Katrusiak, Z. Kristallogr. 2004, 219, 461-467 | Integration Crystal absorption, DAC absorption and gasket shadowing absorption has been applied A. Katrusiak, Z. Kristallogr. 2004, 219, 461-467 |
T_{min}, T_{max} | 0.481, 0.919 | 0.477, 0.865 | 0.479, 0.850 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 293, 48, 48 | 1167, 179, 94 | 1400, 126, 108 |
R_{int} | 0.145 | 0.132 | 0.151 |
θ_{max} (°) | 23.1 | 29.6 | 29.4 |
(sin θ/λ)_{max} (Å^{−}^{1}) | 0.553 | 0.695 | 0.692 |
Refinement | |||
R[F^{2} > 2σ(F^{2})], wR(F^{2}), S | 0.132, 0.295, 1.30 | 0.053, 0.136, 1.03 | 0.142, 0.248, 1.01 |
No. of reflections | 48 | 179 | 126 |
No. of parameters | 13 | 37 | 13 |
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 |
w = 1/[σ^{2}(F_{o}^{2}) + (0.0508P)^{2} + 19.4433P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 | w = 1/[σ^{2}(F_{o}^{2}) + (0.060P)^{2} + 0.030P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 | w = 1/[σ^{2}(F_{o}^{2}) + (0.P)^{2} + 7.984P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 | |
Δρ_{max}, Δρ_{min} (e Å^{−}^{3}) | 0.17, −0.20 | 0.11, −0.09 | 0.13, −0.12 |
Computer programs: CrysAlis CCD 1.171.23 beta (Oxford Diffraction Poland, 2004), CrysAlis RED 1.171.24 beta (Oxford Diffraction Poland, 2004), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).