Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614011226/zb5041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50412PNO_0.71GPasup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50413PNO_0.78GPasup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50415PNO_1.05GPasup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50416PNO_1.18GPasup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50417PNO_2.00GPasup6.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614011226/zb5041sup7.pdf |
CCDC references: 1003288; 1003289; 1003290; 1003291; 1003292
For all compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003); program(s) used to solve structure: SHELXS–97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL–97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL–97 (Sheldrick, 1997).
C5H5NO | Dx = 1.443 Mg m−3 |
Mr = 95.10 | Melting point: 338 K |
Tetragonal, P41212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 4abw 2nw | Cell parameters from 1240 reflections |
a = 5.6634 (8) Å | θ = 5.1–27.4° |
c = 13.645 (3) Å | µ = 0.10 mm−1 |
V = 437.65 (12) Å3 | T = 295 K |
Z = 4 | Tetragonal trapezohedron, colourless |
F(000) = 200 | 0.33 × 0.30 × 0.15 mm |
KM-4 CCD diffractometer | 190 independent reflections |
Radiation source: fine-focus sealed tube | 182 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ– and ω–scans | θmax = 27.4°, θmin = 5.1° |
Absorption correction: numerical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | h = −5→5 |
Tmin = 0.47, Tmax = 0.89 | k = −5→5 |
1240 measured reflections | l = −17→17 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0714P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.100 | (Δ/σ)max < 0.001 |
S = 1.11 | Δρmax = 0.17 e Å−3 |
190 reflections | Δρmin = −0.20 e Å−3 |
35 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.95 (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 | Absolute structure parameter: 2 (6) |
Experimental. Data were collected at room temperature and pressure of 0.71 (2) GPa (710000 kPa) with the crystal obtained by the in situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. |
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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1747 (5) | 0.1747 (5) | 0.0000 | 0.0476 (15) | |
N1 | 0.0106 (5) | 0.0106 (5) | 0.0000 | 0.0301 (13) | |
C1 | 0.0395 (8) | −0.1862 (8) | 0.0554 (2) | 0.0319 (13) | |
H1 | 0.1744 | −0.2043 | 0.0936 | 0.038* | |
C2 | −0.1324 (8) | −0.3597 (9) | 0.0551 (2) | 0.0347 (13) | |
H2 | −0.1116 | −0.4954 | 0.0925 | 0.042* | |
C3 | −0.3333 (8) | −0.3333 (8) | 0.0000 | 0.0421 (16) | |
H3 | −0.4494 | −0.4494 | 0.0000 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.048 (2) | 0.048 (2) | 0.0471 (18) | −0.0109 (18) | −0.0009 (15) | 0.0009 (15) |
N1 | 0.0311 (19) | 0.0311 (19) | 0.0282 (17) | 0.004 (2) | 0.0017 (14) | −0.0017 (14) |
C1 | 0.023 (5) | 0.045 (5) | 0.0275 (13) | 0.0075 (16) | −0.0005 (15) | 0.0029 (19) |
C2 | 0.042 (5) | 0.029 (5) | 0.0339 (14) | 0.0068 (17) | 0.0038 (19) | 0.0037 (16) |
C3 | 0.046 (3) | 0.046 (3) | 0.034 (2) | −0.004 (2) | 0.0042 (17) | −0.0042 (17) |
O1—N1 | 1.314 (6) | C1—C2 | 1.383 (6) |
N1—C1i | 1.357 (5) | C2—C3 | 1.371 (5) |
N1—C1 | 1.357 (5) | C3—C2i | 1.371 (5) |
O1—N1—C1i | 119.7 (2) | N1—C1—C2 | 119.8 (5) |
O1—N1—C1 | 119.7 (2) | C3—C2—C1 | 120.6 (5) |
C1i—N1—C1 | 120.6 (4) | C2—C3—C2i | 118.8 (6) |
Symmetry code: (i) y, x, −z. |
C5H5NO | Dx = 1.447 Mg m−3 |
Mr = 95.10 | Melting point: 338 K |
Tetragonal, P41212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 4abw 2nw | Cell parameters from 1450 reflections |
a = 5.6608 (8) Å | θ = 3.9–26.9° |
c = 13.625 (3) Å | µ = 0.10 mm−1 |
V = 436.61 (12) Å3 | T = 295 K |
Z = 4 | Tetragonal trapezohedron, colourless |
F(000) = 200 | 0.40 × 0.36 × 0.15 mm |
KM-4 CCD diffractometer | 262 independent reflections |
Radiation source: fine-focus sealed tube | 233 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ– and ω–scans | θmax = 26.9°, θmin = 3.9° |
Absorption correction: numerical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | h = −7→7 |
Tmin = 0.47, Tmax = 0.89 | k = −5→5 |
1450 measured reflections | l = −12→12 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0631P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.102 | (Δ/σ)max < 0.001 |
S = 1.15 | Δρmax = 0.21 e Å−3 |
262 reflections | Δρmin = −0.14 e Å−3 |
35 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.55 (8) |
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: 5 (5) |
Experimental. Data were collected at room temperature and pressure of 0.78 (2) GPa (780000 kPa) with the crystal obtained by the in situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. |
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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1754 (3) | 0.1754 (3) | 0.0000 | 0.0483 (10) | |
N1 | 0.0108 (4) | 0.0108 (4) | 0.0000 | 0.0335 (10) | |
C1 | 0.0386 (4) | −0.1863 (5) | 0.0548 (3) | 0.0333 (10) | |
H1 | 0.1736 | −0.2047 | 0.0929 | 0.040* | |
C2 | −0.1312 (4) | −0.3596 (4) | 0.0546 (3) | 0.0363 (10) | |
H2 | −0.1092 | −0.4958 | 0.0916 | 0.044* | |
C3 | −0.3331 (4) | −0.3331 (4) | 0.0000 | 0.0392 (12) | |
H3 | −0.4492 | −0.4492 | 0.0000 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0434 (11) | 0.0434 (11) | 0.058 (3) | −0.0134 (17) | 0.0009 (9) | −0.0009 (9) |
N1 | 0.0342 (14) | 0.0342 (14) | 0.032 (3) | 0.0051 (15) | 0.0026 (10) | −0.0026 (10) |
C1 | 0.0309 (16) | 0.0392 (17) | 0.030 (2) | 0.0111 (14) | −0.0033 (13) | −0.0004 (14) |
C2 | 0.0472 (19) | 0.0306 (16) | 0.031 (3) | 0.0086 (17) | 0.0098 (14) | 0.0063 (11) |
C3 | 0.0370 (16) | 0.0370 (16) | 0.044 (3) | −0.003 (2) | 0.0079 (14) | −0.0079 (14) |
O1—N1 | 1.318 (4) | C1—C2 | 1.373 (4) |
N1—C1i | 1.352 (3) | C2—C3 | 1.371 (3) |
N1—C1 | 1.352 (3) | C3—C2i | 1.371 (3) |
O1—N1—C1i | 120.10 (17) | N1—C1—C2 | 120.5 (3) |
O1—N1—C1 | 120.10 (17) | C3—C2—C1 | 120.4 (3) |
C1i—N1—C1 | 119.8 (3) | C2—C3—C2i | 118.4 (4) |
Symmetry code: (i) y, x, −z. |
C5H5NO | Dx = 1.492 Mg m−3 |
Mr = 95.10 | Melting point: 338 K |
Tetragonal, P41212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 4abw 2nw | Cell parameters from 1100 reflections |
a = 5.5890 (8) Å | θ = 3.9–27.2° |
c = 13.550 (3) Å | µ = 0.11 mm−1 |
V = 423.26 (12) Å3 | T = 295 K |
Z = 4 | Tetragonal trapezohedron, colourless |
F(000) = 200 | 0.51 × 0.30 × 0.15 mm |
KM-4 CCD diffractometer | 181 independent reflections |
Radiation source: fine-focus sealed tube | 159 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ– and ω–scans | θmax = 27.2°, θmin = 3.9° |
Absorption correction: numerical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | h = −2→2 |
Tmin = 0.59, Tmax = 0.92 | k = −6→7 |
1100 measured reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0346P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
181 reflections | Δρmax = 0.08 e Å−3 |
41 parameters | Δρmin = −0.11 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 3 (5) |
Experimental. Data were collected at room temperature and pressure of 1.05 (2) GPa (1050000 kPa) with the crystal obtained by the in situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. |
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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1786 (4) | 0.1786 (4) | 0.0000 | 0.0469 (11) | |
N1 | 0.0135 (6) | 0.0135 (6) | 0.0000 | 0.0323 (11) | |
C1 | 0.0392 (7) | −0.1868 (7) | 0.05564 (16) | 0.0288 (9) | |
C2 | −0.1305 (8) | −0.3604 (7) | 0.05531 (18) | 0.0334 (9) | |
C3 | −0.3351 (6) | −0.3351 (6) | 0.0000 | 0.0321 (13) | |
H1 | 0.188 (4) | −0.171 (5) | 0.0982 (19) | 0.039* | |
H2 | −0.102 (6) | −0.495 (6) | 0.093 (2) | 0.039* | |
H3 | −0.439 (6) | −0.439 (6) | 0.0000 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0428 (16) | 0.0428 (16) | 0.0552 (17) | −0.016 (4) | 0.0029 (10) | −0.0029 (10) |
N1 | 0.0340 (17) | 0.0340 (17) | 0.0290 (16) | 0.008 (5) | 0.0038 (11) | −0.0038 (11) |
C1 | 0.0261 (18) | 0.033 (2) | 0.0272 (12) | 0.003 (3) | 0.0020 (16) | 0.0025 (15) |
C2 | 0.043 (2) | 0.030 (2) | 0.0263 (13) | 0.011 (4) | 0.0077 (19) | 0.0028 (14) |
C3 | 0.033 (2) | 0.033 (2) | 0.0296 (16) | −0.006 (4) | 0.0077 (16) | −0.0077 (16) |
O1—N1 | 1.305 (4) | C2—C3 | 1.374 (4) |
N1—C1i | 1.357 (4) | C2—H2 | 0.92 (4) |
N1—C1 | 1.357 (4) | C3—C2i | 1.374 (4) |
C1—C2 | 1.357 (4) | C3—H3 | 0.82 (5) |
C1—H1 | 1.01 (2) | ||
O1—N1—C1i | 120.6 (3) | C1—C2—C3 | 120.7 (3) |
O1—N1—C1 | 120.6 (3) | C1—C2—H2 | 117 (2) |
C1i—N1—C1 | 118.9 (6) | C3—C2—H2 | 122 (2) |
C2—C1—N1 | 120.9 (4) | C2—C3—C2i | 117.9 (5) |
C2—C1—H1 | 129.4 (16) | C2—C3—H3 | 121.0 (3) |
N1—C1—H1 | 109.4 (17) | C2i—C3—H3 | 121.0 (3) |
Symmetry code: (i) y, x, −z. |
C5H5NO | Dx = 1.508 Mg m−3 |
Mr = 95.10 | Melting point: 338 K |
Tetragonal, P41212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 4abw 2nw | Cell parameters from 1446 reflections |
a = 5.5678 (14) Å | θ = 4.0–26.7° |
c = 13.514 (4) Å | µ = 0.11 mm−1 |
V = 418.95 (19) Å3 | T = 295 K |
Z = 4 | Tetragonal trapezohedron, colourless |
F(000) = 200 | 0.38 × 0.23 × 0.15 mm |
KM-4 CCD diffractometer | 278 independent reflections |
Radiation source: fine-focus sealed tube | 240 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
φ– and ω–scans | θmax = 26.7°, θmin = 4.0° |
Absorption correction: numerical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | h = −6→6 |
Tmin = 0.53, Tmax = 0.88 | k = −3→3 |
1446 measured reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0651P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
278 reflections | Δρmax = 0.13 e Å−3 |
41 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −10 (5) |
Experimental. Data were collected at room temperature and pressure of 1.18 (2) GPa 1180000 kPa) with the crystal obtained by the in situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. |
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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1767 (4) | 0.1767 (4) | 0.0000 | 0.0507 (10) | |
N1 | 0.0108 (5) | 0.0108 (5) | 0.0000 | 0.0321 (10) | |
C1 | 0.0388 (6) | −0.1904 (6) | 0.05523 (18) | 0.0346 (9) | |
C2 | −0.1338 (6) | −0.3655 (6) | 0.05553 (18) | 0.0378 (9) | |
C3 | −0.3412 (6) | −0.3412 (6) | 0.0000 | 0.0366 (11) | |
H1 | 0.184 (6) | −0.192 (6) | 0.0967 (18) | 0.044* | |
H2 | −0.109 (5) | −0.515 (6) | 0.099 (2) | 0.044* | |
H3 | −0.479 (6) | −0.479 (6) | 0.0000 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0477 (14) | 0.0477 (14) | 0.0566 (16) | −0.009 (2) | 0.0026 (10) | −0.0026 (10) |
N1 | 0.0319 (15) | 0.0319 (15) | 0.0325 (14) | 0.0004 (17) | 0.0023 (9) | −0.0023 (9) |
C1 | 0.033 (2) | 0.043 (2) | 0.0281 (12) | 0.0083 (16) | 0.0015 (11) | 0.0023 (13) |
C2 | 0.046 (2) | 0.0356 (19) | 0.0319 (13) | 0.0050 (19) | 0.0059 (13) | 0.0023 (12) |
C3 | 0.0388 (18) | 0.0388 (18) | 0.0321 (17) | −0.002 (3) | 0.0041 (12) | −0.0041 (12) |
O1—N1 | 1.306 (4) | C2—C3 | 1.384 (4) |
N1—C1i | 1.355 (4) | C2—H2 | 1.03 (3) |
N1—C1 | 1.355 (4) | C3—C2i | 1.384 (4) |
C1—C2 | 1.369 (4) | C3—H3 | 1.08 (4) |
C1—H1 | 0.98 (3) | ||
O1—N1—C1i | 120.2 (2) | C1—C2—C3 | 121.0 (3) |
O1—N1—C1 | 120.2 (2) | C1—C2—H2 | 118.9 (15) |
C1i—N1—C1 | 119.6 (4) | C3—C2—H2 | 120.2 (16) |
N1—C1—C2 | 120.6 (3) | C2—C3—C2i | 117.3 (4) |
N1—C1—H1 | 114.7 (18) | C2—C3—H3 | 121.4 (2) |
C2—C1—H1 | 124.5 (18) | C2i—C3—H3 | 121.4 (2) |
Symmetry code: (i) y, x, −z. |
C5H5NO | Dx = 1.567 Mg m−3 |
Mr = 95.10 | Melting point: 338 K |
Tetragonal, P41212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 4abw 2nw | Cell parameters from 882 reflections |
a = 5.4980 (8) Å | θ = 4.0–26.0° |
c = 13.334 (3) Å | µ = 0.11 mm−1 |
V = 403.06 (12) Å3 | T = 295 K |
Z = 4 | Tetragonal trapezohedron, colourless |
F(000) = 200 | 0.34 × 0.24 × 0.15 mm |
KM-4 CCD diffractometer | 179 independent reflections |
Radiation source: fine-focus sealed tube | 170 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ– and ω–scans | θmax = 26.0°, θmin = 4.0° |
Absorption correction: numerical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | h = −6→6 |
Tmin = 0.46, Tmax = 0.91 | k = −2→2 |
882 measured reflections | l = −13→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.176 | w = 1/[σ2(Fo2) + (0.1092P)2 + 0.2482P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max < 0.001 |
179 reflections | Δρmax = 0.20 e Å−3 |
22 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
Experimental. Data were collected at room temperature and pressure of 2.00 (2) GPa (2000000 kPa) with the crystal obtained by the in situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. |
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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1750 (7) | 0.1750 (7) | 0.0000 | 0.0403 (16)* | |
N1 | 0.0071 (8) | 0.0071 (8) | 0.0000 | 0.0295 (18)* | |
C1 | 0.0384 (12) | −0.1994 (11) | 0.0557 (4) | 0.0316 (17)* | |
C2 | −0.1392 (10) | −0.3720 (11) | 0.0550 (4) | 0.0320 (16)* | |
C3 | −0.3501 (10) | −0.3501 (10) | 0.0000 | 0.0329 (19)* | |
H1 | 0.193 (9) | −0.190 (11) | 0.100 (4) | 0.039* | |
H2 | −0.091 (8) | −0.509 (12) | 0.096 (4) | 0.039* | |
H3 | −0.467 (10) | −0.467 (10) | 0.0000 | 0.039* |
O1—N1 | 1.305 (8) | C1—C2 | 1.361 (9) |
N1—C1i | 1.367 (7) | C2—C3 | 1.377 (6) |
N1—C1 | 1.367 (7) | C3—C2i | 1.377 (6) |
O1—N1—C1i | 119.9 (4) | C2—C1—N1 | 119.0 (6) |
O1—N1—C1 | 119.9 (4) | C1—C2—C3 | 123.1 (7) |
C1i—N1—C1 | 120.2 (9) | C2—C3—C2i | 115.5 (9) |
Symmetry code: (i) y, x, −z. |