Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889813006225/kk5130sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889813006225/kk5130Ph2CO2_Xray_295Ksup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889813006225/kk5130Ph2CO2_70K_neutronsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889813006225/kk5130Ph2CO2_300K_neutronsup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0021889813006225/kk5130Ph2CO2_300K_neutronsup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0021889813006225/kk5130Ph2CO2_70K_neutronsup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0021889813006225/kk5130Ph2CO2_Xray_295Ksup7.cml |
CCDC references: 943010; 943011; 943012
Data collection: SXD2001 (Gutmann, 2005) for Ph2CO2_300K_neutron, Ph2CO2_70K_neutron. Cell refinement: SXD2001 (Gutmann, 2005) for Ph2CO2_300K_neutron, Ph2CO2_70K_neutron. Data reduction: SXD2001 (Gutmann, 2005) for Ph2CO2_300K_neutron, Ph2CO2_70K_neutron. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for Ph2CO2_300K_neutron, Ph2CO2_70K_neutron. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: SHELXTL for Ph2CO2_300K_neutron, Ph2CO2_70K_neutron. Software used to prepare material for publication: SHELXTL for Ph2CO2_300K_neutron, Ph2CO2_70K_neutron.
C13H10O | F(000) = 219 |
Mr = 182.22 | Dx = 1.220 Mg m−3 |
Orthorhombic, P212121 | Neutron radiation, λ = 0.4-8.8 Å |
a = 7.979 (3) Å | Cell parameters from 330 reflections |
b = 10.274 (3) Å | µ = 3.78 + 0.0079 * lambda mm−1 |
c = 12.103 (4) Å | T = 300 K |
V = 992.2 (5) Å3 | Block, white transparent |
Z = 4 | 7 × 6 × 2 mm |
SXD diffractometer | 5557 reflections with I > 2σ(I) |
Radiation source: ISIS spallation source | Rint = 0.000 |
time–of–flight LAUE diffraction scans | θmax = 85.2°, θmin = 8.4° |
Absorption correction: gauss integration Gauss integration with 32 grid points | h = −26→12 |
Tmin = 3.364, Tmax = 4.891 | k = −35→31 |
5557 measured reflections | l = −38→32 |
5557 independent reflections |
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)] = 0.090 | w = 1/[σ2(Fo2) + (0.1923P)2 + 1.9468P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.224 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.60 e Å−3 |
5557 reflections | Δρmin = −0.79 e Å−3 |
225 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.204 (7) |
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: −10 (10) |
C13H10O | V = 992.2 (5) Å3 |
Mr = 182.22 | Z = 4 |
Orthorhombic, P212121 | Neutron radiation, λ = 0.4-8.8 Å |
a = 7.979 (3) Å | µ = 3.78 + 0.0079 * lambda mm−1 |
b = 10.274 (3) Å | T = 300 K |
c = 12.103 (4) Å | 7 × 6 × 2 mm |
SXD diffractometer | 5557 independent reflections |
Absorption correction: gauss integration Gauss integration with 32 grid points | 5557 reflections with I > 2σ(I) |
Tmin = 3.364, Tmax = 4.891 | Rint = 0.000 |
5557 measured reflections |
R[F2 > 2σ(F2)] = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.224 | Δρmax = 0.60 e Å−3 |
S = 1.07 | Δρmin = −0.79 e Å−3 |
5557 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
225 parameters | Absolute structure parameter: −10 (10) |
0 restraints |
Experimental. For peak integration a local UB matrix refined for each frame, using approximately 30 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 330 For final cell dimensions a weighted average of all local cells was calculated Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.48–7.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7–2.5 Angstroms. The data collection procedures on the SXD instrument used for the single-crystal neutron data collection are most recently summarized in the Appendix to the following paper Wilson, C·C. (1997). J. Mol. Struct. 405, 207–217 |
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. The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given instead the following limits are given _diffrn_reflns_sin(theta)/lambda_min 0.05 _diffrn_reflns_sin(theta)/lambda_max 1.31 _refine_diff_density_max/min is given in Fermi per per angstrom cubed not electons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the diffracted intensity of a given atom: _refine_diff_density_max = 5% of Carbon _refine_diff_density_min = -4% of Carbon 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. 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 | ||
C1 | 0.1935 (4) | 0.4980 (3) | 0.8995 (2) | 0.0549 (7) | |
H1 | 0.1206 (11) | 0.5524 (6) | 0.9602 (6) | 0.083 (2) | |
C2 | 0.2196 (5) | 0.3660 (3) | 0.9145 (3) | 0.0687 (9) | |
H2 | 0.1676 (15) | 0.3178 (7) | 0.9856 (7) | 0.107 (3) | |
C3 | 0.3097 (5) | 0.2958 (3) | 0.8386 (3) | 0.0756 (10) | |
H3 | 0.3322 (15) | 0.1927 (7) | 0.8506 (10) | 0.121 (4) | |
C4 | 0.3748 (5) | 0.3576 (4) | 0.7456 (3) | 0.0764 (10) | |
H4 | 0.4452 (14) | 0.3029 (10) | 0.6854 (8) | 0.118 (3) | |
C5 | 0.3470 (5) | 0.4904 (3) | 0.7288 (2) | 0.0641 (8) | |
H5 | 0.3919 (13) | 0.5385 (9) | 0.6554 (7) | 0.102 (3) | |
C6 | 0.2562 (4) | 0.5611 (3) | 0.80707 (19) | 0.0516 (7) | |
C7 | 0.2205 (4) | 0.6997 (3) | 0.7817 (2) | 0.0563 (7) | |
C8 | 0.1980 (4) | 0.7961 (2) | 0.8721 (2) | 0.0492 (6) | |
C9 | 0.0984 (4) | 0.9063 (3) | 0.8506 (3) | 0.0614 (8) | |
H6 | 0.0357 (13) | 0.9126 (8) | 0.7719 (7) | 0.095 (2) | |
C10 | 0.0802 (5) | 1.0018 (3) | 0.9299 (3) | 0.0704 (9) | |
H7 | 0.0023 (14) | 1.0848 (8) | 0.9128 (9) | 0.114 (3) | |
C11 | 0.1639 (5) | 0.9915 (3) | 1.0293 (3) | 0.0719 (10) | |
H8 | 0.1517 (15) | 1.0664 (8) | 1.0894 (8) | 0.113 (3) | |
C12 | 0.2639 (5) | 0.8832 (3) | 1.0513 (3) | 0.0638 (9) | |
H9 | 0.3286 (13) | 0.8759 (8) | 1.1296 (7) | 0.102 (3) | |
C13 | 0.2803 (4) | 0.7857 (3) | 0.9732 (2) | 0.0551 (7) | |
H10 | 0.3566 (10) | 0.7014 (7) | 0.9909 (6) | 0.082 (2) | |
O1 | 0.2110 (8) | 0.7343 (4) | 0.6856 (3) | 0.0875 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.066 (2) | 0.0501 (12) | 0.0490 (15) | −0.0009 (15) | 0.0064 (13) | −0.0007 (11) |
H1 | 0.106 (6) | 0.072 (3) | 0.072 (4) | 0.009 (4) | 0.034 (4) | −0.002 (3) |
C2 | 0.088 (3) | 0.0574 (14) | 0.0610 (17) | 0.0002 (16) | 0.0003 (18) | 0.0001 (13) |
H2 | 0.166 (10) | 0.069 (4) | 0.086 (5) | −0.011 (5) | 0.034 (5) | 0.015 (4) |
C3 | 0.087 (3) | 0.0573 (16) | 0.082 (2) | 0.0130 (18) | −0.005 (2) | −0.0120 (16) |
H3 | 0.165 (10) | 0.060 (4) | 0.139 (8) | 0.025 (5) | −0.003 (7) | −0.009 (5) |
C4 | 0.072 (2) | 0.0759 (18) | 0.081 (2) | 0.0060 (17) | 0.0045 (19) | −0.028 (2) |
H4 | 0.116 (7) | 0.117 (6) | 0.119 (7) | 0.015 (6) | 0.041 (6) | −0.042 (6) |
C5 | 0.067 (2) | 0.0761 (17) | 0.0498 (16) | −0.0060 (16) | 0.0119 (14) | −0.0105 (15) |
H5 | 0.120 (7) | 0.121 (6) | 0.064 (4) | −0.011 (5) | 0.031 (4) | −0.004 (4) |
C6 | 0.0591 (17) | 0.0546 (14) | 0.0411 (11) | −0.0057 (13) | 0.0009 (11) | −0.0067 (10) |
C7 | 0.072 (2) | 0.0559 (13) | 0.0410 (12) | −0.0028 (14) | 0.0009 (12) | 0.0035 (10) |
C8 | 0.0517 (17) | 0.0510 (11) | 0.0450 (12) | −0.0015 (11) | −0.0041 (10) | 0.0019 (11) |
C9 | 0.0611 (19) | 0.0565 (15) | 0.066 (2) | 0.0017 (13) | −0.0032 (15) | 0.0144 (14) |
H6 | 0.105 (6) | 0.092 (5) | 0.090 (5) | 0.011 (5) | −0.024 (4) | 0.018 (4) |
C10 | 0.072 (2) | 0.0543 (15) | 0.085 (2) | 0.0075 (16) | 0.0057 (18) | 0.0026 (17) |
H7 | 0.126 (9) | 0.070 (4) | 0.148 (8) | 0.027 (5) | 0.004 (6) | 0.010 (5) |
C11 | 0.080 (3) | 0.0538 (15) | 0.082 (2) | −0.0067 (15) | 0.0217 (18) | −0.0139 (16) |
H8 | 0.159 (9) | 0.082 (4) | 0.100 (5) | 0.014 (5) | 0.012 (5) | −0.040 (4) |
C12 | 0.071 (2) | 0.0618 (15) | 0.0583 (17) | −0.0040 (15) | 0.0002 (15) | −0.0118 (13) |
H9 | 0.132 (8) | 0.106 (5) | 0.069 (4) | −0.005 (5) | −0.031 (4) | −0.026 (4) |
C13 | 0.0582 (19) | 0.0589 (14) | 0.0483 (14) | 0.0031 (14) | −0.0088 (12) | −0.0054 (11) |
H10 | 0.100 (6) | 0.071 (3) | 0.075 (4) | 0.026 (4) | −0.031 (4) | −0.004 (3) |
O1 | 0.141 (4) | 0.077 (2) | 0.0440 (19) | −0.003 (3) | −0.004 (2) | 0.0072 (16) |
C1—C2 | 1.384 (4) | C7—C8 | 1.487 (4) |
C1—C6 | 1.386 (4) | C8—C13 | 1.393 (4) |
C2—C3 | 1.372 (5) | C8—C9 | 1.408 (4) |
C3—C4 | 1.393 (6) | C9—C10 | 1.381 (5) |
C4—C5 | 1.397 (5) | C10—C11 | 1.380 (6) |
C5—C6 | 1.396 (4) | C11—C12 | 1.395 (5) |
C6—C7 | 1.484 (4) | C12—C13 | 1.383 (4) |
C7—O1 | 1.219 (4) | ||
C2—C1—C6 | 120.6 (3) | C6—C7—C8 | 120.6 (2) |
C3—C2—C1 | 120.5 (3) | C13—C8—C9 | 119.3 (3) |
C2—C3—C4 | 119.8 (3) | C13—C8—C7 | 122.6 (2) |
C3—C4—C5 | 120.3 (3) | C9—C8—C7 | 117.9 (3) |
C6—C5—C4 | 119.4 (3) | C10—C9—C8 | 120.2 (3) |
C1—C6—C5 | 119.4 (3) | C11—C10—C9 | 120.0 (3) |
C1—C6—C7 | 123.1 (3) | C10—C11—C12 | 120.3 (3) |
C5—C6—C7 | 117.3 (3) | C13—C12—C11 | 120.1 (3) |
O1—C7—C6 | 119.3 (3) | C12—C13—C8 | 120.0 (3) |
O1—C7—C8 | 120.0 (3) |
C13H10O | F(000) = 219 |
Mr = 182.22 | Dx = 1.275 Mg m−3 |
Orthorhombic, P212121 | Neutron radiation, λ = 0.4-8.8 Å |
a = 7.7145 (15) Å | Cell parameters from 1100 reflections |
b = 10.2301 (15) Å | µ = 3.78 + 0.0079 * lambda mm−1 |
c = 12.0269 (18) Å | T = 70 K |
V = 949.2 (3) Å3 | Block, white transparent |
Z = 4 | 7 × 6 × 2 mm |
SXD diffractometer | 13371 reflections with I > 2σ(I) |
Radiation source: ISIS spallation source | Rint = 0.000 |
time–of–flight LAUE diffraction scans | θmax = 84.0°, θmin = 8.6° |
Absorption correction: gauss integration Gauss integration with 32 grid points | h = −16→13 |
Tmin = 3.360, Tmax = 4.903 | k = −23→22 |
13372 measured reflections | l = −23→29 |
13372 independent reflections |
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)] = 0.091 | w = 1/[σ2(Fo2) + (0.1421P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.207 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 2.67 e Å−3 |
13372 reflections | Δρmin = −1.59 e Å−3 |
225 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0508 (10) |
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: 10 (10) |
C13H10O | V = 949.2 (3) Å3 |
Mr = 182.22 | Z = 4 |
Orthorhombic, P212121 | Neutron radiation, λ = 0.4-8.8 Å |
a = 7.7145 (15) Å | µ = 3.78 + 0.0079 * lambda mm−1 |
b = 10.2301 (15) Å | T = 70 K |
c = 12.0269 (18) Å | 7 × 6 × 2 mm |
SXD diffractometer | 13372 independent reflections |
Absorption correction: gauss integration Gauss integration with 32 grid points | 13371 reflections with I > 2σ(I) |
Tmin = 3.360, Tmax = 4.903 | Rint = 0.000 |
13372 measured reflections |
R[F2 > 2σ(F2)] = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.207 | Δρmax = 2.67 e Å−3 |
S = 1.04 | Δρmin = −1.59 e Å−3 |
13372 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
225 parameters | Absolute structure parameter: 10 (10) |
0 restraints |
Experimental. For peak integration a local UB matrix refined for each frame, using approximately 100 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 1100 For final cell dimensions a weighted average of all local cells was calculated Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.48–7.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7–2.5 Angstroms. The data collection procedures on the SXD instrument used for the single-crystal neutron data collection are most recently summarized in the Appendix to the following paper Wilson, C·C. (1997). J. Mol. Struct. 405, 207–217 |
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. The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given instead the following limits are given _diffrn_reflns_sin(theta)/lambda_min 0.05 _diffrn_reflns_sin(theta)/lambda_max 1.31 _refine_diff_density_max/min is given in Fermi per per angstrom cubed not electons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the diffracted intensity of a given atom: _refine_diff_density_max = 5% of Carbon _refine_diff_density_min = -4% of Carbon 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 | ||
C1 | 0.1924 (2) | 0.49876 (12) | 0.90058 (10) | 0.0097 (2) | |
H1 | 0.1202 (6) | 0.5543 (3) | 0.9617 (3) | 0.0246 (8) | |
C2 | 0.2157 (3) | 0.36513 (13) | 0.91548 (11) | 0.0118 (3) | |
H2 | 0.1646 (7) | 0.3178 (3) | 0.9893 (3) | 0.0295 (9) | |
C3 | 0.3072 (3) | 0.29309 (13) | 0.83674 (12) | 0.0137 (3) | |
H3 | 0.3271 (7) | 0.1890 (3) | 0.8491 (3) | 0.0336 (10) | |
C4 | 0.3743 (2) | 0.35443 (15) | 0.74239 (13) | 0.0129 (3) | |
H4 | 0.4438 (7) | 0.2985 (4) | 0.6806 (3) | 0.0312 (9) | |
C5 | 0.3485 (2) | 0.48732 (14) | 0.72658 (11) | 0.0104 (3) | |
H5 | 0.3982 (7) | 0.5354 (4) | 0.6533 (3) | 0.0280 (9) | |
C6 | 0.2576 (2) | 0.56098 (12) | 0.80560 (10) | 0.0084 (2) | |
C7 | 0.2221 (2) | 0.70125 (12) | 0.78018 (10) | 0.0087 (2) | |
C8 | 0.1972 (2) | 0.79826 (12) | 0.87148 (11) | 0.0082 (2) | |
C9 | 0.0957 (2) | 0.90826 (13) | 0.84850 (11) | 0.0102 (3) | |
H6 | 0.0348 (6) | 0.9147 (4) | 0.7675 (3) | 0.0270 (8) | |
C10 | 0.0750 (2) | 1.00557 (13) | 0.92804 (12) | 0.0120 (3) | |
H7 | −0.0079 (7) | 1.0896 (3) | 0.9110 (4) | 0.0301 (9) | |
C11 | 0.1588 (2) | 0.99473 (14) | 1.03052 (12) | 0.0124 (3) | |
H8 | 0.1435 (7) | 1.0712 (4) | 1.0928 (3) | 0.0332 (10) | |
C12 | 0.2612 (2) | 0.88555 (12) | 1.05347 (11) | 0.0109 (3) | |
H9 | 0.3257 (7) | 0.8778 (4) | 1.1332 (3) | 0.0280 (8) | |
C13 | 0.2802 (2) | 0.78673 (12) | 0.97465 (10) | 0.0091 (2) | |
H10 | 0.3605 (6) | 0.7021 (4) | 0.9931 (3) | 0.0258 (8) | |
O1 | 0.2145 (3) | 0.73700 (16) | 0.68328 (13) | 0.0152 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0139 (8) | 0.0080 (4) | 0.0071 (4) | −0.0007 (5) | 0.0008 (4) | 0.0001 (4) |
H1 | 0.032 (2) | 0.0202 (13) | 0.0219 (14) | 0.0040 (14) | 0.0117 (13) | −0.0023 (10) |
C2 | 0.0167 (9) | 0.0086 (4) | 0.0102 (5) | 0.0007 (5) | 0.0005 (5) | 0.0005 (4) |
H2 | 0.047 (3) | 0.0198 (13) | 0.0217 (14) | 0.0007 (15) | 0.0096 (15) | 0.0057 (11) |
C3 | 0.0187 (9) | 0.0088 (4) | 0.0135 (5) | 0.0021 (5) | −0.0008 (5) | −0.0016 (4) |
H3 | 0.054 (3) | 0.0136 (11) | 0.0329 (18) | 0.0050 (15) | 0.0012 (18) | 0.0014 (11) |
C4 | 0.0125 (9) | 0.0126 (5) | 0.0137 (6) | 0.0012 (5) | 0.0012 (5) | −0.0051 (5) |
H4 | 0.039 (3) | 0.0247 (14) | 0.0298 (17) | 0.0062 (17) | 0.0109 (16) | −0.0094 (13) |
C5 | 0.0110 (8) | 0.0124 (5) | 0.0078 (5) | −0.0002 (5) | 0.0013 (4) | −0.0025 (4) |
H5 | 0.039 (3) | 0.0253 (14) | 0.0192 (13) | −0.0022 (15) | 0.0110 (15) | 0.0010 (11) |
C6 | 0.0110 (8) | 0.0081 (4) | 0.0060 (4) | 0.0003 (5) | 0.0009 (4) | −0.0006 (3) |
C7 | 0.0117 (7) | 0.0088 (4) | 0.0057 (4) | −0.0002 (5) | 0.0000 (4) | 0.0000 (3) |
C8 | 0.0107 (7) | 0.0073 (4) | 0.0067 (4) | 0.0004 (5) | −0.0010 (4) | −0.0002 (3) |
C9 | 0.0118 (8) | 0.0090 (5) | 0.0098 (5) | 0.0003 (5) | −0.0007 (4) | 0.0012 (4) |
H6 | 0.036 (3) | 0.0257 (15) | 0.0195 (14) | 0.0047 (15) | −0.0078 (13) | 0.0023 (11) |
C10 | 0.0147 (9) | 0.0072 (4) | 0.0141 (6) | 0.0017 (5) | 0.0015 (5) | 0.0000 (4) |
H7 | 0.038 (3) | 0.0182 (13) | 0.0338 (18) | 0.0092 (15) | −0.0004 (17) | 0.0016 (13) |
C11 | 0.0155 (9) | 0.0088 (4) | 0.0128 (5) | −0.0009 (5) | 0.0021 (5) | −0.0024 (4) |
H8 | 0.049 (3) | 0.0234 (14) | 0.0270 (16) | 0.0064 (17) | 0.0007 (17) | −0.0136 (13) |
C12 | 0.0144 (9) | 0.0099 (5) | 0.0085 (5) | −0.0009 (5) | −0.0005 (5) | −0.0018 (4) |
H9 | 0.035 (3) | 0.0325 (16) | 0.0168 (13) | 0.0004 (16) | −0.0065 (13) | −0.0029 (12) |
C13 | 0.0109 (8) | 0.0090 (5) | 0.0075 (4) | 0.0008 (5) | −0.0014 (4) | −0.0013 (3) |
H10 | 0.029 (2) | 0.0227 (13) | 0.0255 (15) | 0.0078 (15) | −0.0064 (13) | −0.0008 (12) |
O1 | 0.0272 (12) | 0.0118 (5) | 0.0065 (5) | −0.0013 (7) | −0.0011 (6) | 0.0011 (4) |
C1—C2 | 1.3903 (18) | C7—C8 | 1.4925 (18) |
C1—C6 | 1.4009 (19) | C8—C9 | 1.399 (2) |
C2—C3 | 1.392 (2) | C8—C13 | 1.4012 (19) |
C3—C4 | 1.396 (2) | C9—C10 | 1.390 (2) |
C4—C5 | 1.387 (2) | C10—C11 | 1.397 (2) |
C5—C6 | 1.4010 (19) | C11—C12 | 1.396 (2) |
C6—C7 | 1.4925 (18) | C12—C13 | 1.3936 (18) |
C7—O1 | 1.223 (2) | ||
C2—C1—C6 | 120.37 (13) | C6—C7—C8 | 120.80 (11) |
C1—C2—C3 | 119.88 (14) | C9—C8—C13 | 119.91 (12) |
C2—C3—C4 | 120.19 (13) | C9—C8—C7 | 117.48 (12) |
C5—C4—C3 | 119.92 (14) | C13—C8—C7 | 122.47 (13) |
C4—C5—C6 | 120.39 (14) | C10—C9—C8 | 120.31 (14) |
C1—C6—C5 | 119.23 (12) | C9—C10—C11 | 119.81 (14) |
C1—C6—C7 | 122.55 (13) | C12—C11—C10 | 120.03 (13) |
C5—C6—C7 | 118.03 (12) | C13—C12—C11 | 120.37 (14) |
O1—C7—C6 | 119.44 (13) | C12—C13—C8 | 119.56 (13) |
O1—C7—C8 | 119.75 (13) |
C13H10O | Dx = 1.208 Mg m−3 |
Mr = 182.21 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 623 reflections |
a = 7.9958 (15) Å | θ = 3.2–28.7° |
b = 10.2907 (19) Å | µ = 0.08 mm−1 |
c = 12.174 (2) Å | T = 293 K |
V = 1001.7 (3) Å3 | Block, white transparent |
Z = 4 | 0.1 × 0.1 × 0.1 mm |
F(000) = 384 |
Xcalibur, Sapphire3, Gemini diffractometer | 1915 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1166 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 15.9745 pixels mm-1 | θmax = 28.7°, θmin = 3.2° |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −10→5 |
Tmin = 0.788, Tmax = 1.000 | k = −13→11 |
2828 measured reflections | l = −15→10 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.022P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.079 | (Δ/σ)max < 0.001 |
S = 0.97 | Δρmax = 0.10 e Å−3 |
1915 reflections | Δρmin = −0.10 e Å−3 |
128 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0069 (12) |
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 |
C13H10O | V = 1001.7 (3) Å3 |
Mr = 182.21 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.9958 (15) Å | µ = 0.08 mm−1 |
b = 10.2907 (19) Å | T = 293 K |
c = 12.174 (2) Å | 0.1 × 0.1 × 0.1 mm |
Xcalibur, Sapphire3, Gemini diffractometer | 1915 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | 1166 reflections with I > 2σ(I) |
Tmin = 0.788, Tmax = 1.000 | Rint = 0.021 |
2828 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.10 e Å−3 |
1915 reflections | Δρmin = −0.10 e Å−3 |
128 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
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 | ||
C1 | 0.1940 (3) | 0.4979 (2) | 0.89906 (17) | 0.0602 (6) | |
H1 | 0.1345 | 0.5446 | 0.9515 | 0.072* | |
C2 | 0.2203 (3) | 0.3664 (2) | 0.91343 (19) | 0.0721 (7) | |
H2 | 0.1764 | 0.3246 | 0.9747 | 0.087* | |
C3 | 0.3107 (3) | 0.2974 (2) | 0.8381 (2) | 0.0798 (8) | |
H3 | 0.3293 | 0.2091 | 0.8487 | 0.096* | |
C4 | 0.3740 (3) | 0.3583 (3) | 0.7468 (2) | 0.0790 (8) | |
H4 | 0.4359 | 0.3111 | 0.6960 | 0.095* | |
C5 | 0.3461 (3) | 0.4887 (2) | 0.7303 (2) | 0.0663 (7) | |
H5 | 0.3879 | 0.5290 | 0.6676 | 0.080* | |
C6 | 0.2558 (3) | 0.5608 (2) | 0.80679 (16) | 0.0534 (5) | |
C7 | 0.2199 (3) | 0.7001 (2) | 0.78224 (18) | 0.0599 (6) | |
C8 | 0.1982 (3) | 0.7968 (2) | 0.87218 (17) | 0.0505 (5) | |
C9 | 0.1001 (3) | 0.9054 (2) | 0.8519 (2) | 0.0650 (6) | |
H9 | 0.0457 | 0.9133 | 0.7847 | 0.078* | |
C10 | 0.0822 (3) | 1.0011 (2) | 0.9291 (3) | 0.0779 (7) | |
H10 | 0.0154 | 1.0731 | 0.9146 | 0.093* | |
C11 | 0.1636 (3) | 0.9903 (2) | 1.0284 (3) | 0.0756 (8) | |
H11 | 0.1516 | 1.0551 | 1.0811 | 0.091* | |
C12 | 0.2631 (3) | 0.8833 (2) | 1.05006 (18) | 0.0679 (7) | |
H12 | 0.3191 | 0.8767 | 1.1168 | 0.081* | |
C13 | 0.2791 (3) | 0.7863 (2) | 0.97248 (16) | 0.0568 (6) | |
H13 | 0.3443 | 0.7137 | 0.9876 | 0.068* | |
O1 | 0.2096 (3) | 0.73555 (16) | 0.68655 (12) | 0.0952 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0693 (14) | 0.0595 (13) | 0.0517 (12) | 0.0016 (13) | 0.0019 (14) | −0.0045 (13) |
C2 | 0.0893 (17) | 0.0609 (14) | 0.0661 (15) | −0.0033 (14) | 0.0015 (16) | 0.0004 (14) |
C3 | 0.0881 (19) | 0.0613 (15) | 0.0901 (18) | 0.0071 (15) | −0.0106 (18) | −0.0125 (17) |
C4 | 0.0704 (15) | 0.0813 (19) | 0.0854 (19) | 0.0092 (14) | 0.0098 (16) | −0.0287 (18) |
C5 | 0.0637 (15) | 0.0822 (17) | 0.0530 (13) | −0.0088 (14) | 0.0000 (14) | −0.0110 (15) |
C6 | 0.0574 (13) | 0.0603 (13) | 0.0424 (11) | −0.0033 (12) | −0.0029 (13) | −0.0051 (12) |
C7 | 0.0646 (13) | 0.0667 (14) | 0.0484 (12) | −0.0086 (13) | −0.0023 (14) | 0.0042 (12) |
C8 | 0.0514 (12) | 0.0501 (11) | 0.0499 (12) | −0.0057 (11) | −0.0018 (12) | 0.0064 (11) |
C9 | 0.0651 (14) | 0.0615 (14) | 0.0685 (16) | −0.0039 (13) | −0.0062 (13) | 0.0142 (15) |
C10 | 0.0783 (16) | 0.0567 (15) | 0.099 (2) | 0.0035 (14) | 0.0078 (17) | 0.0079 (18) |
C11 | 0.0826 (18) | 0.0554 (14) | 0.0889 (19) | −0.0079 (14) | 0.0224 (17) | −0.0160 (16) |
C12 | 0.0710 (15) | 0.0718 (16) | 0.0609 (14) | −0.0053 (14) | −0.0009 (15) | −0.0080 (13) |
C13 | 0.0577 (13) | 0.0554 (13) | 0.0572 (13) | 0.0015 (11) | −0.0030 (13) | 0.0004 (12) |
O1 | 0.1531 (16) | 0.0820 (11) | 0.0504 (9) | −0.0103 (13) | −0.0083 (13) | 0.0106 (9) |
C1—C2 | 1.380 (3) | C7—C8 | 1.490 (3) |
C1—C6 | 1.387 (3) | C8—C13 | 1.386 (3) |
C2—C3 | 1.367 (3) | C8—C9 | 1.388 (3) |
C3—C4 | 1.372 (3) | C9—C10 | 1.369 (3) |
C4—C5 | 1.375 (3) | C10—C11 | 1.378 (3) |
C5—C6 | 1.393 (3) | C11—C12 | 1.384 (3) |
C6—C7 | 1.492 (3) | C12—C13 | 1.380 (2) |
C7—O1 | 1.224 (2) | ||
C2—C1—C6 | 120.4 (2) | C8—C7—C6 | 121.13 (18) |
C3—C2—C1 | 120.3 (2) | C13—C8—C9 | 118.9 (2) |
C2—C3—C4 | 120.1 (2) | C13—C8—C7 | 122.78 (18) |
C3—C4—C5 | 120.3 (3) | C9—C8—C7 | 118.2 (2) |
C4—C5—C6 | 120.4 (2) | C10—C9—C8 | 121.1 (2) |
C1—C6—C5 | 118.5 (2) | C9—C10—C11 | 119.7 (2) |
C1—C6—C7 | 122.8 (2) | C10—C11—C12 | 120.2 (2) |
C5—C6—C7 | 118.5 (2) | C13—C12—C11 | 119.9 (2) |
O1—C7—C8 | 119.5 (2) | C12—C13—C8 | 120.25 (19) |
O1—C7—C6 | 119.4 (2) |
Experimental details
(Ph2CO2_300K_neutron) | (Ph2CO2_70K_neutron) | (Ph2CO2_Xray_295K) | |
Crystal data | |||
Chemical formula | C13H10O | C13H10O | C13H10O |
Mr | 182.22 | 182.22 | 182.21 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 | Orthorhombic, P212121 |
Temperature (K) | 300 | 70 | 293 |
a, b, c (Å) | 7.979 (3), 10.274 (3), 12.103 (4) | 7.7145 (15), 10.2301 (15), 12.0269 (18) | 7.9958 (15), 10.2907 (19), 12.174 (2) |
V (Å3) | 992.2 (5) | 949.2 (3) | 1001.7 (3) |
Z | 4 | 4 | 4 |
Radiation type | Neutron, λ = 0.4-8.8 Å | Neutron, λ = 0.4-8.8 Å | Mo Kα |
µ (mm−1) | 3.78 + 0.0079 * lambda | 3.78 + 0.0079 * lambda | 0.08 |
Crystal size (mm) | 7 × 6 × 2 | 7 × 6 × 2 | 0.1 × 0.1 × 0.1 |
Data collection | |||
Diffractometer | SXD diffractometer | SXD diffractometer | Xcalibur, Sapphire3, Gemini diffractometer |
Absorption correction | Gauss integration Gauss integration with 32 grid points | Gauss integration Gauss integration with 32 grid points | Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Tmin, Tmax | 3.364, 4.891 | 3.360, 4.903 | 0.788, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5557, 5557, 5557 | 13372, 13372, 13371 | 2828, 1915, 1166 |
Rint | 0.000 | 0.000 | 0.021 |
Distance from source to specimen (mm) | – | – | 0.675 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.090, 0.224, 1.07 | 0.091, 0.207, 1.04 | 0.048, 0.079, 0.97 |
No. of reflections | 5557 | 13372 | 1915 |
No. of parameters | 225 | 225 | 128 |
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-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.60, −0.79 | 2.67, −1.59 | 0.10, −0.10 |
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 |
Absolute structure parameter | −10 (10) | 10 (10) | ? |
Computer programs: SXD2001 (Gutmann, 2005), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL.