Crystal structures of two polymorphic forms of p-nitrophenol have been determined at several temperatures between 120 and 375 K. The thermal expansion tensor has been determined for both polymorphs. The rigid-body mean-square amplitudes of molecular translations and librations and the amplitudes of the internal torsions of the nitro group have been calculated at different temperatures. Differential scanning calorimetry was used to find the temperature and enthalpy of the polymorphic transformation. The results were compared with those recently obtained for m-nitrophenol polymorphs. Some conclusions concerning the polymorphism of p- and m-nitrophenols are presented.
Supporting information
CCDC references: 298515; 298516; 298517; 298518; 298519; 298520
For all compounds, data collection: KUMA KM4CCD software, 1999; cell refinement: KUMA KM4CCD software, 1999; data reduction: KUMA KM4CCD software, 1999; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
(alfa_6) 4-nitrophenol
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Crystal data top
C6H5NO3 | F(000) = 288 |
Mr = 139.11 | Dx = 1.488 Mg m−3 |
Monoclinic, P21/c? | Mo Kα radiation, λ = 0.71073 Å |
a = 6.138 (2) Å | Cell parameters from 532 reflections |
b = 8.874 (3) Å | θ = 4.1–20.4° |
c = 11.702 (4) Å | µ = 0.12 mm−1 |
β = 103.05 (3)° | T = 298 K |
V = 620.9 (4) Å3 | Thin plate, pale yellow |
Z = 4 | 0.77 × 0.38 × 0.38 mm |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 897 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 27.4°, θmin = 4.3° |
ω scan | h = −7→7 |
2165 measured reflections | k = −11→4 |
1197 independent reflections | l = −13→15 |
Refinement top
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)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.138 | Calculated w = 1/[σ2(Fo2) + (0.0728P)2 + 0.0466P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1197 reflections | Δρmax = 0.16 e Å−3 |
96 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.069 (14) |
Crystal data top
C6H5NO3 | V = 620.9 (4) Å3 |
Mr = 139.11 | Z = 4 |
Monoclinic, P21/c? | Mo Kα radiation |
a = 6.138 (2) Å | µ = 0.12 mm−1 |
b = 8.874 (3) Å | T = 298 K |
c = 11.702 (4) Å | 0.77 × 0.38 × 0.38 mm |
β = 103.05 (3)° | |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 897 reflections with I > 2σ(I) |
2165 measured reflections | Rint = 0.039 |
1197 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.16 e Å−3 |
1197 reflections | Δρmin = −0.13 e Å−3 |
96 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N | 0.2421 (3) | 0.25629 (17) | 0.46598 (13) | 0.0608 (5) | |
O1 | 0.8762 (3) | −0.01405 (18) | 0.81614 (15) | 0.0839 (6) | |
O2 | 0.2924 (2) | 0.36810 (17) | 0.41535 (13) | 0.0858 (6) | |
O3 | 0.0541 (2) | 0.20394 (19) | 0.44253 (13) | 0.0844 (6) | |
C1 | 0.4131 (3) | 0.18660 (18) | 0.55603 (13) | 0.0483 (4) | |
C2 | 0.6259 (3) | 0.24448 (19) | 0.58274 (15) | 0.0534 (5) | |
H2 | 0.6622 | 0.3271 | 0.5419 | 0.064* | |
C3 | 0.7836 (3) | 0.1795 (2) | 0.66989 (16) | 0.0570 (5) | |
H3 | 0.9277 | 0.2188 | 0.6895 | 0.068* | |
C4 | 0.7286 (3) | 0.0551 (2) | 0.72895 (16) | 0.0575 (5) | |
C5 | 0.5157 (3) | −0.0038 (2) | 0.69881 (16) | 0.0623 (5) | |
H5 | 0.4805 | −0.0889 | 0.7374 | 0.075* | |
C6 | 0.3563 (3) | 0.06119 (19) | 0.61307 (16) | 0.0561 (5) | |
H6 | 0.2121 | 0.0220 | 0.5933 | 0.067* | |
H1 | 0.997 (4) | 0.034 (3) | 0.829 (2) | 0.102 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N | 0.0621 (10) | 0.0633 (10) | 0.0541 (9) | −0.0065 (7) | 0.0071 (8) | 0.0015 (7) |
O1 | 0.0821 (12) | 0.0686 (10) | 0.0844 (11) | 0.0038 (8) | −0.0160 (9) | 0.0070 (8) |
O2 | 0.0823 (11) | 0.0817 (11) | 0.0847 (10) | −0.0123 (8) | 0.0005 (8) | 0.0303 (8) |
O3 | 0.0578 (9) | 0.0967 (12) | 0.0880 (11) | −0.0162 (7) | −0.0063 (8) | 0.0151 (8) |
C1 | 0.0515 (10) | 0.0482 (9) | 0.0440 (9) | −0.0025 (7) | 0.0086 (8) | −0.0041 (7) |
C2 | 0.0574 (10) | 0.0475 (9) | 0.0560 (10) | −0.0084 (7) | 0.0146 (8) | −0.0027 (7) |
C3 | 0.0491 (11) | 0.0543 (10) | 0.0649 (11) | −0.0063 (7) | 0.0069 (9) | −0.0114 (8) |
C4 | 0.0620 (12) | 0.0517 (10) | 0.0530 (10) | 0.0047 (8) | 0.0012 (9) | −0.0061 (8) |
C5 | 0.0721 (13) | 0.0569 (11) | 0.0555 (11) | −0.0078 (9) | 0.0096 (10) | 0.0074 (8) |
C6 | 0.0543 (11) | 0.0575 (10) | 0.0563 (10) | −0.0121 (8) | 0.0122 (8) | −0.0026 (8) |
Geometric parameters (Å, º) top
N—O3 | 1.2167 (19) | C1—C6 | 1.382 (2) |
N—O2 | 1.2301 (19) | C2—C3 | 1.365 (3) |
N—C1 | 1.447 (2) | C3—C4 | 1.384 (3) |
O1—C4 | 1.349 (2) | C4—C5 | 1.378 (3) |
C1—C2 | 1.372 (2) | C5—C6 | 1.362 (3) |
| | | |
O3—N—O2 | 121.86 (17) | C2—C3—C4 | 119.85 (17) |
O3—N—C1 | 119.74 (16) | O1—C4—C5 | 117.18 (18) |
O2—N—C1 | 118.40 (15) | O1—C4—C3 | 122.86 (19) |
C2—C1—C6 | 121.50 (17) | C5—C4—C3 | 119.96 (17) |
C2—C1—N | 120.15 (16) | C6—C5—C4 | 120.68 (17) |
C6—C1—N | 118.35 (16) | C5—C6—C1 | 118.62 (17) |
C3—C2—C1 | 119.36 (16) | | |
(al120_5) 4-nitrophenol
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Crystal data top
C6H5NO3 | F(000) = 288 |
Mr = 139.11 | Dx = 1.532 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.136 (1) Å | Cell parameters from 1206 reflections |
b = 8.800 (1) Å | θ = 4.1–27.1° |
c = 11.481 (3) Å | µ = 0.13 mm−1 |
β = 103.40 (2)° | T = 120 K |
V = 603.1 (2) Å3 | Thin plate, pale yellow |
Z = 4 | 0.79 × 0.55 × 0.50 mm |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 906 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
Graphite monochromator | θmax = 27.0°, θmin = 4.4° |
ω scan | h = −3→7 |
1872 measured reflections | k = −11→11 |
1019 independent reflections | l = −14→6 |
Refinement top
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)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | Calculated w = 1/[σ2(Fo2) + (0.0474P)2 + 0.2271P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1019 reflections | Δρmax = 0.21 e Å−3 |
112 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.063 (8) |
Crystal data top
C6H5NO3 | V = 603.1 (2) Å3 |
Mr = 139.11 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.136 (1) Å | µ = 0.13 mm−1 |
b = 8.800 (1) Å | T = 120 K |
c = 11.481 (3) Å | 0.79 × 0.55 × 0.50 mm |
β = 103.40 (2)° | |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 906 reflections with I > 2σ(I) |
1872 measured reflections | Rint = 0.046 |
1019 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.21 e Å−3 |
1019 reflections | Δρmin = −0.21 e Å−3 |
112 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.88161 (19) | 0.02262 (12) | 0.81840 (11) | 0.0305 (3) | |
O2 | 0.04892 (16) | −0.20669 (12) | 0.44182 (11) | 0.0302 (4) | |
C4 | 0.4116 (2) | −0.18532 (15) | 0.55471 (13) | 0.0188 (4) | |
O3 | 0.29073 (17) | −0.37300 (12) | 0.41382 (11) | 0.0312 (3) | |
C5 | 0.3531 (2) | −0.05889 (15) | 0.61380 (14) | 0.0221 (4) | |
C6 | 0.5148 (2) | 0.00938 (16) | 0.70099 (15) | 0.0240 (4) | |
N | 0.24002 (19) | −0.25856 (13) | 0.46497 (12) | 0.0226 (3) | |
C1 | 0.7324 (2) | −0.04842 (15) | 0.73039 (14) | 0.0218 (4) | |
C2 | 0.7891 (2) | −0.17382 (15) | 0.66843 (15) | 0.0217 (4) | |
C3 | 0.6291 (2) | −0.24203 (15) | 0.58029 (14) | 0.0208 (4) | |
H3 | 0.666 (3) | −0.3268 (19) | 0.5388 (15) | 0.022 (4)* | |
H2 | 0.939 (3) | −0.2128 (18) | 0.6900 (16) | 0.028 (4)* | |
H5 | 0.198 (3) | −0.0198 (19) | 0.5918 (15) | 0.025 (4)* | |
H6 | 0.478 (3) | 0.092 (2) | 0.7430 (17) | 0.035 (5)* | |
H1 | 1.002 (4) | −0.030 (3) | 0.838 (2) | 0.063 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0291 (6) | 0.0259 (5) | 0.0306 (8) | −0.0018 (4) | −0.0052 (6) | −0.0021 (5) |
O2 | 0.0187 (5) | 0.0354 (6) | 0.0330 (9) | 0.0064 (4) | −0.0014 (5) | −0.0039 (5) |
C4 | 0.0201 (6) | 0.0205 (6) | 0.0149 (9) | 0.0001 (5) | 0.0020 (7) | 0.0029 (6) |
O3 | 0.0286 (5) | 0.0300 (6) | 0.0326 (8) | 0.0042 (4) | 0.0023 (5) | −0.0116 (5) |
C5 | 0.0210 (6) | 0.0232 (6) | 0.0228 (9) | 0.0031 (5) | 0.0066 (7) | 0.0021 (6) |
C6 | 0.0281 (7) | 0.0210 (6) | 0.0233 (10) | 0.0025 (5) | 0.0070 (7) | −0.0014 (6) |
N | 0.0226 (6) | 0.0234 (6) | 0.0216 (9) | 0.0024 (4) | 0.0045 (6) | 0.0008 (5) |
C1 | 0.0235 (7) | 0.0209 (6) | 0.0193 (9) | −0.0036 (5) | 0.0016 (7) | 0.0032 (6) |
C2 | 0.0185 (6) | 0.0223 (6) | 0.0235 (10) | 0.0014 (5) | 0.0033 (7) | 0.0054 (6) |
C3 | 0.0223 (7) | 0.0186 (6) | 0.0228 (10) | 0.0032 (5) | 0.0080 (7) | 0.0024 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.3497 (19) | O3—N | 1.2412 (15) |
O2—N | 1.2286 (15) | C5—C6 | 1.374 (2) |
C4—C3 | 1.3907 (18) | C6—C1 | 1.395 (2) |
C4—C5 | 1.3929 (19) | C1—C2 | 1.400 (2) |
C4—N | 1.4432 (19) | C2—C3 | 1.374 (2) |
| | | |
C3—C4—C5 | 121.79 (14) | O3—N—C4 | 118.60 (11) |
C3—C4—N | 119.74 (12) | O1—C1—C6 | 117.23 (13) |
C5—C4—N | 118.46 (12) | O1—C1—C2 | 122.68 (13) |
C6—C5—C4 | 118.68 (13) | C6—C1—C2 | 120.09 (14) |
C5—C6—C1 | 120.40 (13) | C3—C2—C1 | 119.94 (13) |
O2—N—O3 | 122.03 (13) | C2—C3—C4 | 119.06 (13) |
O2—N—C4 | 119.37 (12) | | |
(al333_5) 4-nitrophenol
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Crystal data top
C6H5NO3 | F(000) = 288 |
Mr = 139.11 | Dx = 1.474 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.146 (1) Å | Cell parameters from 665 reflections |
b = 8.903 (2) Å | θ = 4.0–21.7° |
c = 11.763 (5) Å | µ = 0.12 mm−1 |
β = 103.09 (3)° | T = 333 K |
V = 626.9 (3) Å3 | Thin plate, pale yellow |
Z = 4 | 0.79 × 0.55 × 0.50 mm |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 725 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 27.4°, θmin = 4.3° |
ω scan | h = −4→7 |
2046 measured reflections | k = −11→11 |
1067 independent reflections | l = −14→7 |
Refinement top
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)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.167 | Calculated w = 1/[σ2(Fo2) + (0.090P)2 + 0.0545P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.016 |
1067 reflections | Δρmax = 0.16 e Å−3 |
112 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.095 (19) |
Crystal data top
C6H5NO3 | V = 626.9 (3) Å3 |
Mr = 139.11 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.146 (1) Å | µ = 0.12 mm−1 |
b = 8.903 (2) Å | T = 333 K |
c = 11.763 (5) Å | 0.79 × 0.55 × 0.50 mm |
β = 103.09 (3)° | |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 725 reflections with I > 2σ(I) |
2046 measured reflections | Rint = 0.029 |
1067 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.167 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.16 e Å−3 |
1067 reflections | Δρmin = −0.12 e Å−3 |
112 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.1247 (4) | −0.0116 (2) | 0.1843 (2) | 0.0991 (8) | |
O2 | 0.9450 (3) | 0.2033 (2) | 0.55718 (18) | 0.0987 (8) | |
O3 | 0.7074 (3) | 0.3670 (2) | 0.58425 (18) | 0.1006 (8) | |
N | 0.7574 (3) | 0.2557 (2) | 0.53377 (19) | 0.0717 (7) | |
C1 | 0.2719 (4) | 0.0572 (3) | 0.2714 (2) | 0.0675 (7) | |
C2 | 0.2171 (4) | 0.1807 (2) | 0.3299 (2) | 0.0669 (7) | |
C3 | 0.3745 (4) | 0.2451 (2) | 0.4162 (2) | 0.0637 (7) | |
C4 | 0.5873 (3) | 0.1869 (2) | 0.44417 (18) | 0.0558 (6) | |
C5 | 0.6432 (4) | 0.0621 (2) | 0.3872 (2) | 0.0653 (7) | |
C6 | 0.4844 (5) | −0.0023 (3) | 0.3018 (3) | 0.0733 (7) | |
H5 | 0.341 (3) | 0.327 (3) | 0.455 (2) | 0.069 (6)* | |
H3 | 0.803 (4) | 0.020 (2) | 0.414 (2) | 0.081 (7)* | |
H6 | 0.076 (4) | 0.225 (3) | 0.311 (2) | 0.085 (7)* | |
H2 | 0.512 (5) | −0.086 (3) | 0.261 (3) | 0.096 (8)* | |
H1 | 0.004 (7) | 0.041 (5) | 0.171 (4) | 0.151 (17)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1001 (14) | 0.0811 (12) | 0.0971 (19) | −0.0032 (10) | −0.0172 (13) | −0.0069 (11) |
O2 | 0.0667 (11) | 0.1140 (15) | 0.1029 (19) | 0.0164 (9) | −0.0071 (11) | −0.0170 (12) |
O3 | 0.0972 (13) | 0.0949 (13) | 0.1001 (17) | 0.0141 (10) | 0.0019 (12) | −0.0347 (12) |
N | 0.0721 (12) | 0.0752 (12) | 0.0650 (15) | 0.0064 (10) | 0.0094 (11) | −0.0031 (11) |
C1 | 0.0726 (13) | 0.0597 (11) | 0.0635 (18) | −0.0038 (10) | 0.0014 (12) | 0.0068 (11) |
C2 | 0.0587 (12) | 0.0631 (12) | 0.076 (2) | 0.0070 (10) | 0.0095 (13) | 0.0137 (12) |
C3 | 0.0680 (13) | 0.0556 (11) | 0.0689 (18) | 0.0085 (9) | 0.0185 (12) | 0.0015 (11) |
C4 | 0.0597 (11) | 0.0577 (10) | 0.0492 (16) | 0.0019 (9) | 0.0104 (11) | 0.0040 (10) |
C5 | 0.0655 (13) | 0.0658 (12) | 0.0648 (17) | 0.0110 (10) | 0.0148 (12) | 0.0022 (12) |
C6 | 0.0867 (16) | 0.0647 (12) | 0.0668 (19) | 0.0087 (12) | 0.0143 (14) | −0.0066 (13) |
Geometric parameters (Å, º) top
O1—C1 | 1.350 (3) | C1—C6 | 1.380 (3) |
O2—N | 1.216 (2) | C2—C3 | 1.360 (3) |
O3—N | 1.230 (2) | C3—C4 | 1.375 (3) |
N—C4 | 1.442 (3) | C4—C5 | 1.380 (3) |
C1—C2 | 1.379 (3) | C5—C6 | 1.359 (4) |
| | | |
O2—N—O3 | 121.8 (2) | C2—C3—C4 | 119.8 (2) |
O2—N—C4 | 119.7 (2) | C3—C4—C5 | 121.0 (2) |
O3—N—C4 | 118.4 (2) | C3—C4—N | 120.5 (2) |
O1—C1—C2 | 122.9 (2) | C5—C4—N | 118.53 (19) |
O1—C1—C6 | 117.0 (2) | C6—C5—C4 | 118.9 (2) |
C2—C1—C6 | 120.0 (2) | C5—C6—C1 | 120.5 (2) |
C3—C2—C1 | 119.7 (2) | | |
(betdc6) 4-nitrophenol
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Crystal data top
C6H5NO3 | Dx = 1.496 Mg m−3 |
Mr = 139.11 | Melting point: 384K K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 3.774 (1) Å | Cell parameters from 805 reflections |
b = 11.147 (4) Å | θ = 4.0–22.5° |
c = 14.695 (3) Å | µ = 0.12 mm−1 |
β = 92.60 (2)° | T = 293 K |
V = 617.6 (3) Å3 | Needle, pale yellow |
Z = 4 | 0.82 × 0.36 × 0.25 mm |
F(000) = 288 | |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 830 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 27.2°, θmin = 5.5° |
ω scan | h = −4→3 |
1991 measured reflections | k = −13→7 |
1140 independent reflections | l = −18→18 |
Refinement top
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)] = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.201 | w = 1/[σ2(Fo2) + (0.0639P)2 + 0.6259P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max = 0.005 |
1140 reflections | Δρmax = 0.18 e Å−3 |
112 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.019 (9) |
Crystal data top
C6H5NO3 | V = 617.6 (3) Å3 |
Mr = 139.11 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.774 (1) Å | µ = 0.12 mm−1 |
b = 11.147 (4) Å | T = 293 K |
c = 14.695 (3) Å | 0.82 × 0.36 × 0.25 mm |
β = 92.60 (2)° | |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 830 reflections with I > 2σ(I) |
1991 measured reflections | Rint = 0.041 |
1140 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.073 | 0 restraints |
wR(F2) = 0.201 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | Δρmax = 0.18 e Å−3 |
1140 reflections | Δρmin = −0.18 e Å−3 |
112 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N | −0.2005 (9) | 0.7396 (3) | 0.4939 (2) | 0.0596 (10) | |
O1 | 0.0815 (9) | 0.5394 (3) | 0.16181 (19) | 0.0673 (9) | |
O2 | −0.3609 (9) | 0.6775 (3) | 0.5476 (2) | 0.0825 (12) | |
O3 | −0.1121 (11) | 0.8431 (3) | 0.5113 (2) | 0.0904 (13) | |
C1 | 0.0170 (9) | 0.5939 (3) | 0.2415 (2) | 0.0457 (9) | |
C2 | 0.0906 (10) | 0.7138 (4) | 0.2589 (3) | 0.0484 (10) | |
C3 | 0.0213 (10) | 0.7617 (4) | 0.3423 (3) | 0.0506 (10) | |
C4 | −0.1185 (9) | 0.6892 (3) | 0.4068 (2) | 0.0442 (9) | |
C5 | −0.1907 (9) | 0.5698 (4) | 0.3903 (2) | 0.0471 (9) | |
C6 | −0.1206 (10) | 0.5218 (4) | 0.3078 (3) | 0.0497 (10) | |
H1 | 0.137 (13) | 0.597 (5) | 0.125 (4) | 0.083 (17)* | |
H2 | 0.182 (11) | 0.761 (4) | 0.212 (3) | 0.066 (12)* | |
H3 | 0.051 (11) | 0.841 (4) | 0.358 (3) | 0.068 (13)* | |
H5 | −0.288 (11) | 0.523 (4) | 0.438 (3) | 0.068 (12)* | |
H6 | −0.171 (9) | 0.440 (4) | 0.294 (2) | 0.050 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N | 0.066 (2) | 0.062 (2) | 0.0507 (18) | −0.0028 (17) | 0.0054 (15) | −0.0015 (18) |
O1 | 0.092 (2) | 0.063 (2) | 0.0484 (16) | 0.0086 (17) | 0.0151 (15) | −0.0021 (16) |
O2 | 0.109 (3) | 0.089 (3) | 0.0517 (17) | −0.016 (2) | 0.0277 (17) | 0.0048 (17) |
O3 | 0.130 (3) | 0.070 (2) | 0.073 (2) | −0.018 (2) | 0.028 (2) | −0.0190 (19) |
C1 | 0.051 (2) | 0.046 (2) | 0.0411 (18) | 0.0051 (15) | 0.0032 (14) | 0.0031 (17) |
C2 | 0.053 (2) | 0.046 (2) | 0.0465 (19) | −0.0006 (17) | 0.0102 (15) | 0.0088 (18) |
C3 | 0.056 (2) | 0.045 (2) | 0.050 (2) | −0.0040 (17) | 0.0036 (16) | 0.0026 (19) |
C4 | 0.0436 (18) | 0.051 (2) | 0.0379 (17) | 0.0010 (15) | 0.0036 (13) | 0.0014 (17) |
C5 | 0.0454 (19) | 0.052 (2) | 0.0438 (18) | −0.0031 (16) | 0.0068 (14) | 0.0099 (18) |
C6 | 0.053 (2) | 0.041 (2) | 0.055 (2) | −0.0034 (16) | 0.0016 (16) | −0.0001 (19) |
Geometric parameters (Å, º) top
N—O3 | 1.224 (4) | C1—C2 | 1.386 (5) |
N—O2 | 1.230 (4) | C2—C3 | 1.373 (5) |
N—C4 | 1.445 (5) | C3—C4 | 1.370 (5) |
O1—C1 | 1.351 (4) | C4—C5 | 1.377 (5) |
C1—C6 | 1.383 (5) | C5—C6 | 1.362 (5) |
| | | |
O3—N—O2 | 122.3 (4) | C4—C3—C2 | 118.8 (4) |
O3—N—C4 | 119.0 (3) | C3—C4—C5 | 121.9 (3) |
O2—N—C4 | 118.7 (3) | C3—C4—N | 119.2 (3) |
O1—C1—C6 | 116.0 (3) | C5—C4—N | 118.9 (3) |
O1—C1—C2 | 123.5 (3) | C6—C5—C4 | 119.4 (3) |
C6—C1—C2 | 120.5 (3) | C5—C6—C1 | 119.6 (4) |
C3—C2—C1 | 119.8 (4) | | |
(be120_9) 4-nitrophenol
top
Crystal data top
C6H5NO3 | Dx = 1.550 Mg m−3 |
Mr = 139.11 | Melting point: 384 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 3.678 (1) Å | Cell parameters from 796 reflections |
b = 11.091 (2) Å | θ = 3.9–25.3° |
c = 14.627 (3) Å | µ = 0.13 mm−1 |
β = 92.75 (3)° | T = 120 K |
V = 596.0 (2) Å3 | Needle, pale yellow |
Z = 4 | 0.57 × 0.55 × 0.53 mm |
F(000) = 288 | |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 913 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 27.3°, θmin = 4.6° |
ω scan | h = −4→2 |
2008 measured reflections | k = −13→12 |
1018 independent reflections | l = −14→17 |
Refinement top
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)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.2706P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.004 |
1018 reflections | Δρmax = 0.20 e Å−3 |
96 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.015 (6) |
Crystal data top
C6H5NO3 | V = 596.0 (2) Å3 |
Mr = 139.11 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.678 (1) Å | µ = 0.13 mm−1 |
b = 11.091 (2) Å | T = 120 K |
c = 14.627 (3) Å | 0.57 × 0.55 × 0.53 mm |
β = 92.75 (3)° | |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 913 reflections with I > 2σ(I) |
2008 measured reflections | Rint = 0.015 |
1018 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.20 e Å−3 |
1018 reflections | Δρmin = −0.27 e Å−3 |
96 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N | −0.1913 (3) | 0.73628 (11) | 0.99181 (11) | 0.0221 (4) | |
O1 | 0.0874 (3) | 0.53655 (10) | 0.65552 (9) | 0.0254 (3) | |
O2 | −0.3612 (3) | 0.67489 (10) | 1.04568 (9) | 0.0301 (4) | |
O3 | −0.0904 (3) | 0.83991 (10) | 1.01088 (9) | 0.0326 (4) | |
C1 | 0.0267 (4) | 0.58952 (13) | 0.73624 (12) | 0.0190 (4) | |
C2 | 0.1057 (4) | 0.71058 (12) | 0.75491 (12) | 0.0201 (4) | |
H2 | 0.2054 | 0.7597 | 0.7092 | 0.024* | |
C3 | 0.0400 (4) | 0.75890 (12) | 0.83899 (12) | 0.0197 (4) | |
H3 | 0.0947 | 0.8410 | 0.8520 | 0.024* | |
C4 | −0.1078 (4) | 0.68561 (12) | 0.90484 (12) | 0.0183 (4) | |
C5 | −0.1877 (4) | 0.56465 (12) | 0.88775 (12) | 0.0192 (4) | |
H5 | −0.2884 | 0.5158 | 0.9335 | 0.023* | |
C6 | −0.1185 (4) | 0.51738 (12) | 0.80379 (12) | 0.0197 (4) | |
H6 | −0.1697 | 0.4349 | 0.7914 | 0.024* | |
H1 | 0.183 (6) | 0.585 (2) | 0.6176 (17) | 0.046 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N | 0.0227 (7) | 0.0205 (6) | 0.0232 (11) | −0.0011 (5) | 0.0016 (6) | −0.0001 (5) |
O1 | 0.0345 (7) | 0.0212 (6) | 0.0210 (9) | 0.0016 (4) | 0.0066 (5) | −0.0012 (4) |
O2 | 0.0393 (7) | 0.0304 (6) | 0.0212 (9) | −0.0060 (5) | 0.0085 (6) | 0.0011 (5) |
O3 | 0.0448 (7) | 0.0239 (6) | 0.0299 (10) | −0.0080 (5) | 0.0096 (6) | −0.0080 (5) |
C1 | 0.0175 (7) | 0.0210 (7) | 0.0184 (11) | 0.0039 (5) | −0.0004 (6) | −0.0007 (6) |
C2 | 0.0190 (7) | 0.0191 (7) | 0.0222 (11) | −0.0011 (5) | 0.0023 (6) | 0.0040 (6) |
C3 | 0.0193 (7) | 0.0162 (6) | 0.0235 (12) | −0.0004 (5) | −0.0004 (6) | 0.0008 (5) |
C4 | 0.0166 (7) | 0.0199 (7) | 0.0182 (11) | 0.0008 (5) | −0.0001 (6) | −0.0008 (6) |
C5 | 0.0165 (7) | 0.0190 (7) | 0.0221 (12) | −0.0012 (5) | −0.0002 (6) | 0.0032 (5) |
C6 | 0.0184 (7) | 0.0155 (6) | 0.0251 (12) | −0.0004 (5) | −0.0001 (7) | 0.0007 (6) |
Geometric parameters (Å, º) top
N—O2 | 1.2337 (17) | C1—C2 | 1.398 (2) |
N—O3 | 1.2356 (17) | C2—C3 | 1.374 (2) |
N—C4 | 1.437 (2) | C3—C4 | 1.391 (2) |
O1—C1 | 1.347 (2) | C4—C5 | 1.393 (2) |
C1—C6 | 1.397 (2) | C5—C6 | 1.370 (2) |
| | | |
O2—N—O3 | 121.66 (15) | C2—C3—C4 | 118.91 (13) |
O2—N—C4 | 119.06 (12) | C3—C4—C5 | 121.64 (15) |
O3—N—C4 | 119.27 (13) | C3—C4—N | 119.45 (13) |
O1—C1—C6 | 117.07 (13) | C5—C4—N | 118.88 (13) |
O1—C1—C2 | 123.26 (14) | C6—C5—C4 | 118.85 (14) |
C6—C1—C2 | 119.66 (15) | C5—C6—C1 | 120.56 (13) |
C3—C2—C1 | 120.38 (14) | | |
(pnif3754) 4-nitrophenol
top
Crystal data top
C6H5NO3 | Dx = 1.468 Mg m−3 |
Mr = 139.11 | Melting point: 384K K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 3.831 (1) Å | Cell parameters from 1153 reflections |
b = 11.093 (2) Å | θ = 3.6–22.9° |
c = 14.835 (3) Å | µ = 0.12 mm−1 |
β = 93.45 (3)° | T = 375 K |
V = 629.3 (2) Å3 | Needle, pale yellow |
Z = 4 | 0.98 × 0.53 × 0.45 mm |
F(000) = 288 | |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 1165 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.061 |
Graphite monochromator | θmax = 31.4°, θmin = 5.4° |
ω scan | h = −2→5 |
4985 measured reflections | k = −16→16 |
1955 independent reflections | l = −21→21 |
Refinement top
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)] = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.294 | w = 1/[σ2(Fo2) + (0.1467P)2 + 0.0501P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max = 0.022 |
1955 reflections | Δρmax = 0.26 e Å−3 |
112 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.05 (3) |
Crystal data top
C6H5NO3 | V = 629.3 (2) Å3 |
Mr = 139.11 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.831 (1) Å | µ = 0.12 mm−1 |
b = 11.093 (2) Å | T = 375 K |
c = 14.835 (3) Å | 0.98 × 0.53 × 0.45 mm |
β = 93.45 (3)° | |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 1165 reflections with I > 2σ(I) |
4985 measured reflections | Rint = 0.061 |
1955 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.078 | 0 restraints |
wR(F2) = 0.294 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | Δρmax = 0.26 e Å−3 |
1955 reflections | Δρmin = −0.22 e Å−3 |
112 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N | −0.2067 (6) | 0.2435 (2) | 0.99594 (14) | 0.0797 (7) | |
O1 | 0.0736 (6) | 0.04282 (18) | 0.66656 (13) | 0.0886 (6) | |
O2 | −0.3598 (7) | 0.1803 (2) | 1.04908 (14) | 0.1116 (9) | |
O3 | −0.1235 (9) | 0.3468 (2) | 1.01367 (19) | 0.1251 (10) | |
C1 | 0.0112 (5) | 0.0971 (2) | 0.74600 (14) | 0.0616 (6) | |
C2 | 0.0792 (6) | 0.2171 (2) | 0.76264 (15) | 0.0649 (6) | |
C3 | 0.0117 (6) | 0.2663 (2) | 0.84548 (15) | 0.0667 (6) | |
C4 | −0.1259 (5) | 0.19319 (19) | 0.90950 (14) | 0.0599 (5) | |
C5 | −0.1928 (5) | 0.0730 (2) | 0.89397 (15) | 0.0632 (6) | |
C6 | −0.1233 (6) | 0.0251 (2) | 0.81166 (17) | 0.0666 (6) | |
H5 | −0.281 (7) | 0.026 (3) | 0.944 (2) | 0.083 (8)* | |
H6 | −0.175 (8) | −0.065 (3) | 0.802 (2) | 0.094 (8)* | |
H3 | 0.070 (7) | 0.350 (3) | 0.866 (2) | 0.088 (8)* | |
H2 | 0.168 (8) | 0.264 (3) | 0.719 (2) | 0.089 (8)* | |
H1 | 0.169 (11) | 0.104 (5) | 0.625 (3) | 0.144 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N | 0.0944 (14) | 0.0850 (15) | 0.0603 (11) | 0.0058 (11) | 0.0089 (9) | −0.0033 (10) |
O1 | 0.1260 (15) | 0.0761 (12) | 0.0660 (11) | 0.0092 (10) | 0.0234 (10) | −0.0051 (8) |
O2 | 0.154 (2) | 0.1214 (18) | 0.0629 (11) | −0.0072 (14) | 0.0372 (12) | 0.0049 (11) |
O3 | 0.184 (3) | 0.0986 (17) | 0.0956 (17) | −0.0173 (16) | 0.0327 (16) | −0.0314 (13) |
C1 | 0.0640 (11) | 0.0642 (11) | 0.0570 (11) | 0.0077 (8) | 0.0066 (8) | 0.0024 (9) |
C2 | 0.0740 (12) | 0.0618 (12) | 0.0603 (12) | −0.0023 (9) | 0.0141 (9) | 0.0131 (9) |
C3 | 0.0770 (13) | 0.0547 (11) | 0.0684 (13) | −0.0026 (9) | 0.0056 (10) | 0.0066 (9) |
C4 | 0.0617 (10) | 0.0678 (12) | 0.0507 (10) | 0.0039 (9) | 0.0058 (8) | 0.0030 (8) |
C5 | 0.0663 (11) | 0.0657 (12) | 0.0577 (11) | −0.0056 (8) | 0.0043 (8) | 0.0130 (9) |
C6 | 0.0745 (12) | 0.0578 (11) | 0.0675 (13) | −0.0043 (9) | 0.0057 (9) | 0.0034 (9) |
Geometric parameters (Å, º) top
N—O3 | 1.215 (3) | C1—C6 | 1.383 (3) |
N—O2 | 1.230 (3) | C2—C3 | 1.383 (3) |
N—C4 | 1.449 (3) | C3—C4 | 1.378 (3) |
O1—C1 | 1.357 (3) | C4—C5 | 1.374 (3) |
C1—C2 | 1.376 (3) | C5—C6 | 1.373 (3) |
| | | |
O3—N—O2 | 121.9 (2) | C4—C3—C2 | 118.7 (2) |
O3—N—C4 | 119.2 (2) | C5—C4—C3 | 122.1 (2) |
O2—N—C4 | 118.9 (2) | C5—C4—N | 118.31 (19) |
O1—C1—C2 | 122.92 (19) | C3—C4—N | 119.6 (2) |
O1—C1—C6 | 116.6 (2) | C6—C5—C4 | 118.74 (18) |
C2—C1—C6 | 120.5 (2) | C5—C6—C1 | 120.2 (2) |
C1—C2—C3 | 119.87 (18) | | |
Experimental details
| (alfa_6) | (al120_5) | (al333_5) | (betdc6) |
Crystal data |
Chemical formula | C6H5NO3 | C6H5NO3 | C6H5NO3 | C6H5NO3 |
Mr | 139.11 | 139.11 | 139.11 | 139.11 |
Crystal system, space group | Monoclinic, P21/c? | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/n |
Temperature (K) | 298 | 120 | 333 | 293 |
a, b, c (Å) | 6.138 (2), 8.874 (3), 11.702 (4) | 6.136 (1), 8.800 (1), 11.481 (3) | 6.146 (1), 8.903 (2), 11.763 (5) | 3.774 (1), 11.147 (4), 14.695 (3) |
β (°) | 103.05 (3) | 103.40 (2) | 103.09 (3) | 92.60 (2) |
V (Å3) | 620.9 (4) | 603.1 (2) | 626.9 (3) | 617.6 (3) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.12 | 0.13 | 0.12 | 0.12 |
Crystal size (mm) | 0.77 × 0.38 × 0.38 | 0.79 × 0.55 × 0.50 | 0.79 × 0.55 × 0.50 | 0.82 × 0.36 × 0.25 |
|
Data collection |
Diffractometer | KUMA Diffraction KM4CCD diffractometer | KUMA Diffraction KM4CCD diffractometer | KUMA Diffraction KM4CCD diffractometer | KUMA Diffraction KM4CCD diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2165, 1197, 897 | 1872, 1019, 906 | 2046, 1067, 725 | 1991, 1140, 830 |
Rint | 0.039 | 0.046 | 0.029 | 0.041 |
(sin θ/λ)max (Å−1) | 0.647 | 0.640 | 0.648 | 0.643 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.138, 1.08 | 0.033, 0.095, 1.08 | 0.048, 0.167, 1.09 | 0.073, 0.201, 1.19 |
No. of reflections | 1197 | 1019 | 1067 | 1140 |
No. of parameters | 96 | 112 | 112 | 112 |
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 | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.13 | 0.21, −0.21 | 0.16, −0.12 | 0.18, −0.18 |
| (be120_9) | (pnif3754) |
Crystal data |
Chemical formula | C6H5NO3 | C6H5NO3 |
Mr | 139.11 | 139.11 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 120 | 375 |
a, b, c (Å) | 3.678 (1), 11.091 (2), 14.627 (3) | 3.831 (1), 11.093 (2), 14.835 (3) |
β (°) | 92.75 (3) | 93.45 (3) |
V (Å3) | 596.0 (2) | 629.3 (2) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.13 | 0.12 |
Crystal size (mm) | 0.57 × 0.55 × 0.53 | 0.98 × 0.53 × 0.45 |
|
Data collection |
Diffractometer | KUMA Diffraction KM4CCD diffractometer | KUMA Diffraction KM4CCD diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2008, 1018, 913 | 4985, 1955, 1165 |
Rint | 0.015 | 0.061 |
(sin θ/λ)max (Å−1) | 0.645 | 0.732 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.104, 1.05 | 0.078, 0.294, 1.16 |
No. of reflections | 1018 | 1955 |
No. of parameters | 96 | 112 |
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 |
Δρmax, Δρmin (e Å−3) | 0.20, −0.27 | 0.26, −0.22 |