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Highly hygroscopic pyridine N-oxide, C5H5NO, dissolves in water absorbed from atmospheric air, but it crystallizes in the neat form of the aqueous solution under high pressure. The crystals grown at high-pressure isochoric conditions are of the same phase as that obtained from anhydrous crystallization at ambient pressure. This feature can be employed for retrieving compounds highly soluble in water from their aqueous solutions. The crystal structure is strongly stabilized by CH...O contacts. The crystal compression and thermal expansion as well as three shortest H...O distances comply with the inverse-relationship rule of pressure and temperature changes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614011226/zb5041sup1.cif
Contains datablocks 2PNO_0.71GPa, 3PNO_0.78GPa, 5PNO_1.05GPa, 6PNO_1.18GPa, 7PNO_2.00GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50412PNO_0.71GPasup2.hkl
Contains datablock 2PNO_0.71GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50413PNO_0.78GPasup3.hkl
Contains datablock 3PNO_0.78GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50415PNO_1.05GPasup4.hkl
Contains datablock 5PNO_1.05GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50416PNO_1.18GPasup5.hkl
Contains datablock 6PNO_1.1GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011226/zb50417PNO_2.00GPasup6.hkl
Contains datablock 7PNO_2.00GPa

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614011226/zb5041sup7.pdf
Detailed structural information and photographs illustrating the isochoric crystallization

CCDC references: 1003288; 1003289; 1003290; 1003291; 1003292

Computing details top

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).

(2PNO_0.71GPa) 'Pyridine-N-oxide' top
Crystal data top
C5H5NODx = 1.443 Mg m3
Mr = 95.10Melting point: 338 K
Tetragonal, P41212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4abw 2nwCell parameters from 1240 reflections
a = 5.6634 (8) Åθ = 5.1–27.4°
c = 13.645 (3) ŵ = 0.10 mm1
V = 437.65 (12) Å3T = 295 K
Z = 4Tetragonal trapezohedron, colourless
F(000) = 2000.33 × 0.30 × 0.15 mm
Data collection top
KM-4 CCD
diffractometer
190 independent reflections
Radiation source: fine-focus sealed tube182 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
φ– and ω–scansθmax = 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 = 55
Tmin = 0.47, Tmax = 0.89k = 55
1240 measured reflectionsl = 1717
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.11Δρmax = 0.17 e Å3
190 reflectionsΔρmin = 0.20 e Å3
35 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.95 (12)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 2 (6)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1747 (5)0.1747 (5)0.00000.0476 (15)
N10.0106 (5)0.0106 (5)0.00000.0301 (13)
C10.0395 (8)0.1862 (8)0.0554 (2)0.0319 (13)
H10.17440.20430.09360.038*
C20.1324 (8)0.3597 (9)0.0551 (2)0.0347 (13)
H20.11160.49540.09250.042*
C30.3333 (8)0.3333 (8)0.00000.0421 (16)
H30.44940.44940.00000.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.048 (2)0.048 (2)0.0471 (18)0.0109 (18)0.0009 (15)0.0009 (15)
N10.0311 (19)0.0311 (19)0.0282 (17)0.004 (2)0.0017 (14)0.0017 (14)
C10.023 (5)0.045 (5)0.0275 (13)0.0075 (16)0.0005 (15)0.0029 (19)
C20.042 (5)0.029 (5)0.0339 (14)0.0068 (17)0.0038 (19)0.0037 (16)
C30.046 (3)0.046 (3)0.034 (2)0.004 (2)0.0042 (17)0.0042 (17)
Geometric parameters (Å, º) top
O1—N11.314 (6)C1—C21.383 (6)
N1—C1i1.357 (5)C2—C31.371 (5)
N1—C11.357 (5)C3—C2i1.371 (5)
O1—N1—C1i119.7 (2)N1—C1—C2119.8 (5)
O1—N1—C1119.7 (2)C3—C2—C1120.6 (5)
C1i—N1—C1120.6 (4)C2—C3—C2i118.8 (6)
Symmetry code: (i) y, x, z.
(3PNO_0.78GPa) 'Pyridine-N-oxide' top
Crystal data top
C5H5NODx = 1.447 Mg m3
Mr = 95.10Melting point: 338 K
Tetragonal, P41212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4abw 2nwCell parameters from 1450 reflections
a = 5.6608 (8) Åθ = 3.9–26.9°
c = 13.625 (3) ŵ = 0.10 mm1
V = 436.61 (12) Å3T = 295 K
Z = 4Tetragonal trapezohedron, colourless
F(000) = 2000.40 × 0.36 × 0.15 mm
Data collection top
KM-4 CCD
diffractometer
262 independent reflections
Radiation source: fine-focus sealed tube233 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
φ– and ω–scansθmax = 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 = 77
Tmin = 0.47, Tmax = 0.89k = 55
1450 measured reflectionsl = 1212
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.15Δρmax = 0.21 e Å3
262 reflectionsΔρmin = 0.14 e Å3
35 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.55 (8)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 5 (5)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1754 (3)0.1754 (3)0.00000.0483 (10)
N10.0108 (4)0.0108 (4)0.00000.0335 (10)
C10.0386 (4)0.1863 (5)0.0548 (3)0.0333 (10)
H10.17360.20470.09290.040*
C20.1312 (4)0.3596 (4)0.0546 (3)0.0363 (10)
H20.10920.49580.09160.044*
C30.3331 (4)0.3331 (4)0.00000.0392 (12)
H30.44920.44920.00000.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0434 (11)0.0434 (11)0.058 (3)0.0134 (17)0.0009 (9)0.0009 (9)
N10.0342 (14)0.0342 (14)0.032 (3)0.0051 (15)0.0026 (10)0.0026 (10)
C10.0309 (16)0.0392 (17)0.030 (2)0.0111 (14)0.0033 (13)0.0004 (14)
C20.0472 (19)0.0306 (16)0.031 (3)0.0086 (17)0.0098 (14)0.0063 (11)
C30.0370 (16)0.0370 (16)0.044 (3)0.003 (2)0.0079 (14)0.0079 (14)
Geometric parameters (Å, º) top
O1—N11.318 (4)C1—C21.373 (4)
N1—C1i1.352 (3)C2—C31.371 (3)
N1—C11.352 (3)C3—C2i1.371 (3)
O1—N1—C1i120.10 (17)N1—C1—C2120.5 (3)
O1—N1—C1120.10 (17)C3—C2—C1120.4 (3)
C1i—N1—C1119.8 (3)C2—C3—C2i118.4 (4)
Symmetry code: (i) y, x, z.
(5PNO_1.05GPa) 'Pyridine-N-oxide' top
Crystal data top
C5H5NODx = 1.492 Mg m3
Mr = 95.10Melting point: 338 K
Tetragonal, P41212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4abw 2nwCell parameters from 1100 reflections
a = 5.5890 (8) Åθ = 3.9–27.2°
c = 13.550 (3) ŵ = 0.11 mm1
V = 423.26 (12) Å3T = 295 K
Z = 4Tetragonal trapezohedron, colourless
F(000) = 2000.51 × 0.30 × 0.15 mm
Data collection top
KM-4 CCD
diffractometer
181 independent reflections
Radiation source: fine-focus sealed tube159 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ– and ω–scansθmax = 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 = 22
Tmin = 0.59, Tmax = 0.92k = 67
1100 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H 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 reflectionsΔρmax = 0.08 e Å3
41 parametersΔρmin = 0.11 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 3 (5)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1786 (4)0.1786 (4)0.00000.0469 (11)
N10.0135 (6)0.0135 (6)0.00000.0323 (11)
C10.0392 (7)0.1868 (7)0.05564 (16)0.0288 (9)
C20.1305 (8)0.3604 (7)0.05531 (18)0.0334 (9)
C30.3351 (6)0.3351 (6)0.00000.0321 (13)
H10.188 (4)0.171 (5)0.0982 (19)0.039*
H20.102 (6)0.495 (6)0.093 (2)0.039*
H30.439 (6)0.439 (6)0.00000.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0428 (16)0.0428 (16)0.0552 (17)0.016 (4)0.0029 (10)0.0029 (10)
N10.0340 (17)0.0340 (17)0.0290 (16)0.008 (5)0.0038 (11)0.0038 (11)
C10.0261 (18)0.033 (2)0.0272 (12)0.003 (3)0.0020 (16)0.0025 (15)
C20.043 (2)0.030 (2)0.0263 (13)0.011 (4)0.0077 (19)0.0028 (14)
C30.033 (2)0.033 (2)0.0296 (16)0.006 (4)0.0077 (16)0.0077 (16)
Geometric parameters (Å, º) top
O1—N11.305 (4)C2—C31.374 (4)
N1—C1i1.357 (4)C2—H20.92 (4)
N1—C11.357 (4)C3—C2i1.374 (4)
C1—C21.357 (4)C3—H30.82 (5)
C1—H11.01 (2)
O1—N1—C1i120.6 (3)C1—C2—C3120.7 (3)
O1—N1—C1120.6 (3)C1—C2—H2117 (2)
C1i—N1—C1118.9 (6)C3—C2—H2122 (2)
C2—C1—N1120.9 (4)C2—C3—C2i117.9 (5)
C2—C1—H1129.4 (16)C2—C3—H3121.0 (3)
N1—C1—H1109.4 (17)C2i—C3—H3121.0 (3)
Symmetry code: (i) y, x, z.
(6PNO_1.18GPa) 'Pyridine-N-oxide' top
Crystal data top
C5H5NODx = 1.508 Mg m3
Mr = 95.10Melting point: 338 K
Tetragonal, P41212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4abw 2nwCell parameters from 1446 reflections
a = 5.5678 (14) Åθ = 4.0–26.7°
c = 13.514 (4) ŵ = 0.11 mm1
V = 418.95 (19) Å3T = 295 K
Z = 4Tetragonal trapezohedron, colourless
F(000) = 2000.38 × 0.23 × 0.15 mm
Data collection top
KM-4 CCD
diffractometer
278 independent reflections
Radiation source: fine-focus sealed tube240 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
φ– and ω–scansθmax = 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 = 66
Tmin = 0.53, Tmax = 0.88k = 33
1446 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H 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 reflectionsΔρmax = 0.13 e Å3
41 parametersΔρmin = 0.14 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 10 (5)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1767 (4)0.1767 (4)0.00000.0507 (10)
N10.0108 (5)0.0108 (5)0.00000.0321 (10)
C10.0388 (6)0.1904 (6)0.05523 (18)0.0346 (9)
C20.1338 (6)0.3655 (6)0.05553 (18)0.0378 (9)
C30.3412 (6)0.3412 (6)0.00000.0366 (11)
H10.184 (6)0.192 (6)0.0967 (18)0.044*
H20.109 (5)0.515 (6)0.099 (2)0.044*
H30.479 (6)0.479 (6)0.00000.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0477 (14)0.0477 (14)0.0566 (16)0.009 (2)0.0026 (10)0.0026 (10)
N10.0319 (15)0.0319 (15)0.0325 (14)0.0004 (17)0.0023 (9)0.0023 (9)
C10.033 (2)0.043 (2)0.0281 (12)0.0083 (16)0.0015 (11)0.0023 (13)
C20.046 (2)0.0356 (19)0.0319 (13)0.0050 (19)0.0059 (13)0.0023 (12)
C30.0388 (18)0.0388 (18)0.0321 (17)0.002 (3)0.0041 (12)0.0041 (12)
Geometric parameters (Å, º) top
O1—N11.306 (4)C2—C31.384 (4)
N1—C1i1.355 (4)C2—H21.03 (3)
N1—C11.355 (4)C3—C2i1.384 (4)
C1—C21.369 (4)C3—H31.08 (4)
C1—H10.98 (3)
O1—N1—C1i120.2 (2)C1—C2—C3121.0 (3)
O1—N1—C1120.2 (2)C1—C2—H2118.9 (15)
C1i—N1—C1119.6 (4)C3—C2—H2120.2 (16)
N1—C1—C2120.6 (3)C2—C3—C2i117.3 (4)
N1—C1—H1114.7 (18)C2—C3—H3121.4 (2)
C2—C1—H1124.5 (18)C2i—C3—H3121.4 (2)
Symmetry code: (i) y, x, z.
(7PNO_2.00GPa) 'Pyridine-N-oxide' top
Crystal data top
C5H5NODx = 1.567 Mg m3
Mr = 95.10Melting point: 338 K
Tetragonal, P41212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4abw 2nwCell parameters from 882 reflections
a = 5.4980 (8) Åθ = 4.0–26.0°
c = 13.334 (3) ŵ = 0.11 mm1
V = 403.06 (12) Å3T = 295 K
Z = 4Tetragonal trapezohedron, colourless
F(000) = 2000.34 × 0.24 × 0.15 mm
Data collection top
KM-4 CCD
diffractometer
179 independent reflections
Radiation source: fine-focus sealed tube170 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ– and ω–scansθmax = 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 = 66
Tmin = 0.46, Tmax = 0.91k = 22
882 measured reflectionsl = 1314
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H 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 reflectionsΔρmax = 0.20 e Å3
22 parametersΔρmin = 0.16 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0 (10)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1750 (7)0.1750 (7)0.00000.0403 (16)*
N10.0071 (8)0.0071 (8)0.00000.0295 (18)*
C10.0384 (12)0.1994 (11)0.0557 (4)0.0316 (17)*
C20.1392 (10)0.3720 (11)0.0550 (4)0.0320 (16)*
C30.3501 (10)0.3501 (10)0.00000.0329 (19)*
H10.193 (9)0.190 (11)0.100 (4)0.039*
H20.091 (8)0.509 (12)0.096 (4)0.039*
H30.467 (10)0.467 (10)0.00000.039*
Geometric parameters (Å, º) top
O1—N11.305 (8)C1—C21.361 (9)
N1—C1i1.367 (7)C2—C31.377 (6)
N1—C11.367 (7)C3—C2i1.377 (6)
O1—N1—C1i119.9 (4)C2—C1—N1119.0 (6)
O1—N1—C1119.9 (4)C1—C2—C3123.1 (7)
C1i—N1—C1120.2 (9)C2—C3—C2i115.5 (9)
Symmetry code: (i) y, x, z.
 

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