Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810503418X/ns0011sup1.cif
Contains datablocks alfa_6, al120_5, al333_5, betdc6, be120_9, pnif3754

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S010876810503418X/ns0011alpha_6sup2.fcf
Contains datablock alfa_6

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S010876810503418X/ns0011al120_5sup3.fcf
Contains datablock al120_5

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S010876810503418X/ns0011al333_5sup4.fcf
Contains datablock al333_5

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S010876810503418X/ns0011betdc6sup5.fcf
Contains datablock betdc6

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S010876810503418X/ns0011be120_9sup6.fcf
Contains datablock be120_9

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S010876810503418X/ns0011pnif3754sup7.fcf
Contains datablock pnif3754

CCDC references: 298515; 298516; 298517; 298518; 298519; 298520

Computing details top

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).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
(alfa_6) 4-nitrophenol top
Crystal data top
C6H5NO3F(000) = 288
Mr = 139.11Dx = 1.488 Mg m3
Monoclinic, P21/c?Mo Kα radiation, λ = 0.71073 Å
a = 6.138 (2) ÅCell parameters from 532 reflections
b = 8.874 (3) Åθ = 4.1–20.4°
c = 11.702 (4) ŵ = 0.12 mm1
β = 103.05 (3)°T = 298 K
V = 620.9 (4) Å3Thin plate, pale yellow
Z = 40.77 × 0.38 × 0.38 mm
Data collection top
KUMA Diffraction KM4CCD
diffractometer
897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 27.4°, θmin = 4.3°
ω scanh = 77
2165 measured reflectionsk = 114
1197 independent reflectionsl = 1315
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)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138Calculated w = 1/[σ2(Fo2) + (0.0728P)2 + 0.0466P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
1197 reflectionsΔρmax = 0.16 e Å3
96 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.069 (14)
Crystal data top
C6H5NO3V = 620.9 (4) Å3
Mr = 139.11Z = 4
Monoclinic, P21/c?Mo Kα radiation
a = 6.138 (2) ŵ = 0.12 mm1
b = 8.874 (3) ÅT = 298 K
c = 11.702 (4) Å0.77 × 0.38 × 0.38 mm
β = 103.05 (3)°
Data collection top
KUMA Diffraction KM4CCD
diffractometer
897 reflections with I > 2σ(I)
2165 measured reflectionsRint = 0.039
1197 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.16 e Å3
1197 reflectionsΔρmin = 0.13 e Å3
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
xyzUiso*/Ueq
N0.2421 (3)0.25629 (17)0.46598 (13)0.0608 (5)
O10.8762 (3)0.01405 (18)0.81614 (15)0.0839 (6)
O20.2924 (2)0.36810 (17)0.41535 (13)0.0858 (6)
O30.0541 (2)0.20394 (19)0.44253 (13)0.0844 (6)
C10.4131 (3)0.18660 (18)0.55603 (13)0.0483 (4)
C20.6259 (3)0.24448 (19)0.58274 (15)0.0534 (5)
H20.66220.32710.54190.064*
C30.7836 (3)0.1795 (2)0.66989 (16)0.0570 (5)
H30.92770.21880.68950.068*
C40.7286 (3)0.0551 (2)0.72895 (16)0.0575 (5)
C50.5157 (3)0.0038 (2)0.69881 (16)0.0623 (5)
H50.48050.08890.73740.075*
C60.3563 (3)0.06119 (19)0.61307 (16)0.0561 (5)
H60.21210.02200.59330.067*
H10.997 (4)0.034 (3)0.829 (2)0.102 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0621 (10)0.0633 (10)0.0541 (9)0.0065 (7)0.0071 (8)0.0015 (7)
O10.0821 (12)0.0686 (10)0.0844 (11)0.0038 (8)0.0160 (9)0.0070 (8)
O20.0823 (11)0.0817 (11)0.0847 (10)0.0123 (8)0.0005 (8)0.0303 (8)
O30.0578 (9)0.0967 (12)0.0880 (11)0.0162 (7)0.0063 (8)0.0151 (8)
C10.0515 (10)0.0482 (9)0.0440 (9)0.0025 (7)0.0086 (8)0.0041 (7)
C20.0574 (10)0.0475 (9)0.0560 (10)0.0084 (7)0.0146 (8)0.0027 (7)
C30.0491 (11)0.0543 (10)0.0649 (11)0.0063 (7)0.0069 (9)0.0114 (8)
C40.0620 (12)0.0517 (10)0.0530 (10)0.0047 (8)0.0012 (9)0.0061 (8)
C50.0721 (13)0.0569 (11)0.0555 (11)0.0078 (9)0.0096 (10)0.0074 (8)
C60.0543 (11)0.0575 (10)0.0563 (10)0.0121 (8)0.0122 (8)0.0026 (8)
Geometric parameters (Å, º) top
N—O31.2167 (19)C1—C61.382 (2)
N—O21.2301 (19)C2—C31.365 (3)
N—C11.447 (2)C3—C41.384 (3)
O1—C41.349 (2)C4—C51.378 (3)
C1—C21.372 (2)C5—C61.362 (3)
O3—N—O2121.86 (17)C2—C3—C4119.85 (17)
O3—N—C1119.74 (16)O1—C4—C5117.18 (18)
O2—N—C1118.40 (15)O1—C4—C3122.86 (19)
C2—C1—C6121.50 (17)C5—C4—C3119.96 (17)
C2—C1—N120.15 (16)C6—C5—C4120.68 (17)
C6—C1—N118.35 (16)C5—C6—C1118.62 (17)
C3—C2—C1119.36 (16)
(al120_5) 4-nitrophenol top
Crystal data top
C6H5NO3F(000) = 288
Mr = 139.11Dx = 1.532 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.136 (1) ÅCell parameters from 1206 reflections
b = 8.800 (1) Åθ = 4.1–27.1°
c = 11.481 (3) ŵ = 0.13 mm1
β = 103.40 (2)°T = 120 K
V = 603.1 (2) Å3Thin plate, pale yellow
Z = 40.79 × 0.55 × 0.50 mm
Data collection top
KUMA Diffraction KM4CCD
diffractometer
906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 27.0°, θmin = 4.4°
ω scanh = 37
1872 measured reflectionsk = 1111
1019 independent reflectionsl = 146
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)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095Calculated w = 1/[σ2(Fo2) + (0.0474P)2 + 0.2271P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
1019 reflectionsΔρmax = 0.21 e Å3
112 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.063 (8)
Crystal data top
C6H5NO3V = 603.1 (2) Å3
Mr = 139.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.136 (1) ŵ = 0.13 mm1
b = 8.800 (1) ÅT = 120 K
c = 11.481 (3) Å0.79 × 0.55 × 0.50 mm
β = 103.40 (2)°
Data collection top
KUMA Diffraction KM4CCD
diffractometer
906 reflections with I > 2σ(I)
1872 measured reflectionsRint = 0.046
1019 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.21 e Å3
1019 reflectionsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
O10.88161 (19)0.02262 (12)0.81840 (11)0.0305 (3)
O20.04892 (16)0.20669 (12)0.44182 (11)0.0302 (4)
C40.4116 (2)0.18532 (15)0.55471 (13)0.0188 (4)
O30.29073 (17)0.37300 (12)0.41382 (11)0.0312 (3)
C50.3531 (2)0.05889 (15)0.61380 (14)0.0221 (4)
C60.5148 (2)0.00938 (16)0.70099 (15)0.0240 (4)
N0.24002 (19)0.25856 (13)0.46497 (12)0.0226 (3)
C10.7324 (2)0.04842 (15)0.73039 (14)0.0218 (4)
C20.7891 (2)0.17382 (15)0.66843 (15)0.0217 (4)
C30.6291 (2)0.24203 (15)0.58029 (14)0.0208 (4)
H30.666 (3)0.3268 (19)0.5388 (15)0.022 (4)*
H20.939 (3)0.2128 (18)0.6900 (16)0.028 (4)*
H50.198 (3)0.0198 (19)0.5918 (15)0.025 (4)*
H60.478 (3)0.092 (2)0.7430 (17)0.035 (5)*
H11.002 (4)0.030 (3)0.838 (2)0.063 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0291 (6)0.0259 (5)0.0306 (8)0.0018 (4)0.0052 (6)0.0021 (5)
O20.0187 (5)0.0354 (6)0.0330 (9)0.0064 (4)0.0014 (5)0.0039 (5)
C40.0201 (6)0.0205 (6)0.0149 (9)0.0001 (5)0.0020 (7)0.0029 (6)
O30.0286 (5)0.0300 (6)0.0326 (8)0.0042 (4)0.0023 (5)0.0116 (5)
C50.0210 (6)0.0232 (6)0.0228 (9)0.0031 (5)0.0066 (7)0.0021 (6)
C60.0281 (7)0.0210 (6)0.0233 (10)0.0025 (5)0.0070 (7)0.0014 (6)
N0.0226 (6)0.0234 (6)0.0216 (9)0.0024 (4)0.0045 (6)0.0008 (5)
C10.0235 (7)0.0209 (6)0.0193 (9)0.0036 (5)0.0016 (7)0.0032 (6)
C20.0185 (6)0.0223 (6)0.0235 (10)0.0014 (5)0.0033 (7)0.0054 (6)
C30.0223 (7)0.0186 (6)0.0228 (10)0.0032 (5)0.0080 (7)0.0024 (6)
Geometric parameters (Å, º) top
O1—C11.3497 (19)O3—N1.2412 (15)
O2—N1.2286 (15)C5—C61.374 (2)
C4—C31.3907 (18)C6—C11.395 (2)
C4—C51.3929 (19)C1—C21.400 (2)
C4—N1.4432 (19)C2—C31.374 (2)
C3—C4—C5121.79 (14)O3—N—C4118.60 (11)
C3—C4—N119.74 (12)O1—C1—C6117.23 (13)
C5—C4—N118.46 (12)O1—C1—C2122.68 (13)
C6—C5—C4118.68 (13)C6—C1—C2120.09 (14)
C5—C6—C1120.40 (13)C3—C2—C1119.94 (13)
O2—N—O3122.03 (13)C2—C3—C4119.06 (13)
O2—N—C4119.37 (12)
(al333_5) 4-nitrophenol top
Crystal data top
C6H5NO3F(000) = 288
Mr = 139.11Dx = 1.474 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.146 (1) ÅCell parameters from 665 reflections
b = 8.903 (2) Åθ = 4.0–21.7°
c = 11.763 (5) ŵ = 0.12 mm1
β = 103.09 (3)°T = 333 K
V = 626.9 (3) Å3Thin plate, pale yellow
Z = 40.79 × 0.55 × 0.50 mm
Data collection top
KUMA Diffraction KM4CCD
diffractometer
725 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 27.4°, θmin = 4.3°
ω scanh = 47
2046 measured reflectionsk = 1111
1067 independent reflectionsl = 147
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)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167Calculated w = 1/[σ2(Fo2) + (0.090P)2 + 0.0545P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.016
1067 reflectionsΔρmax = 0.16 e Å3
112 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.095 (19)
Crystal data top
C6H5NO3V = 626.9 (3) Å3
Mr = 139.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.146 (1) ŵ = 0.12 mm1
b = 8.903 (2) ÅT = 333 K
c = 11.763 (5) Å0.79 × 0.55 × 0.50 mm
β = 103.09 (3)°
Data collection top
KUMA Diffraction KM4CCD
diffractometer
725 reflections with I > 2σ(I)
2046 measured reflectionsRint = 0.029
1067 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.16 e Å3
1067 reflectionsΔρmin = 0.12 e Å3
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
xyzUiso*/Ueq
O10.1247 (4)0.0116 (2)0.1843 (2)0.0991 (8)
O20.9450 (3)0.2033 (2)0.55718 (18)0.0987 (8)
O30.7074 (3)0.3670 (2)0.58425 (18)0.1006 (8)
N0.7574 (3)0.2557 (2)0.53377 (19)0.0717 (7)
C10.2719 (4)0.0572 (3)0.2714 (2)0.0675 (7)
C20.2171 (4)0.1807 (2)0.3299 (2)0.0669 (7)
C30.3745 (4)0.2451 (2)0.4162 (2)0.0637 (7)
C40.5873 (3)0.1869 (2)0.44417 (18)0.0558 (6)
C50.6432 (4)0.0621 (2)0.3872 (2)0.0653 (7)
C60.4844 (5)0.0023 (3)0.3018 (3)0.0733 (7)
H50.341 (3)0.327 (3)0.455 (2)0.069 (6)*
H30.803 (4)0.020 (2)0.414 (2)0.081 (7)*
H60.076 (4)0.225 (3)0.311 (2)0.085 (7)*
H20.512 (5)0.086 (3)0.261 (3)0.096 (8)*
H10.004 (7)0.041 (5)0.171 (4)0.151 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1001 (14)0.0811 (12)0.0971 (19)0.0032 (10)0.0172 (13)0.0069 (11)
O20.0667 (11)0.1140 (15)0.1029 (19)0.0164 (9)0.0071 (11)0.0170 (12)
O30.0972 (13)0.0949 (13)0.1001 (17)0.0141 (10)0.0019 (12)0.0347 (12)
N0.0721 (12)0.0752 (12)0.0650 (15)0.0064 (10)0.0094 (11)0.0031 (11)
C10.0726 (13)0.0597 (11)0.0635 (18)0.0038 (10)0.0014 (12)0.0068 (11)
C20.0587 (12)0.0631 (12)0.076 (2)0.0070 (10)0.0095 (13)0.0137 (12)
C30.0680 (13)0.0556 (11)0.0689 (18)0.0085 (9)0.0185 (12)0.0015 (11)
C40.0597 (11)0.0577 (10)0.0492 (16)0.0019 (9)0.0104 (11)0.0040 (10)
C50.0655 (13)0.0658 (12)0.0648 (17)0.0110 (10)0.0148 (12)0.0022 (12)
C60.0867 (16)0.0647 (12)0.0668 (19)0.0087 (12)0.0143 (14)0.0066 (13)
Geometric parameters (Å, º) top
O1—C11.350 (3)C1—C61.380 (3)
O2—N1.216 (2)C2—C31.360 (3)
O3—N1.230 (2)C3—C41.375 (3)
N—C41.442 (3)C4—C51.380 (3)
C1—C21.379 (3)C5—C61.359 (4)
O2—N—O3121.8 (2)C2—C3—C4119.8 (2)
O2—N—C4119.7 (2)C3—C4—C5121.0 (2)
O3—N—C4118.4 (2)C3—C4—N120.5 (2)
O1—C1—C2122.9 (2)C5—C4—N118.53 (19)
O1—C1—C6117.0 (2)C6—C5—C4118.9 (2)
C2—C1—C6120.0 (2)C5—C6—C1120.5 (2)
C3—C2—C1119.7 (2)
(betdc6) 4-nitrophenol top
Crystal data top
C6H5NO3Dx = 1.496 Mg m3
Mr = 139.11Melting point: 384K K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 3.774 (1) ÅCell parameters from 805 reflections
b = 11.147 (4) Åθ = 4.0–22.5°
c = 14.695 (3) ŵ = 0.12 mm1
β = 92.60 (2)°T = 293 K
V = 617.6 (3) Å3Needle, pale yellow
Z = 40.82 × 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 tubeRint = 0.041
Graphite monochromatorθmax = 27.2°, θmin = 5.5°
ω scanh = 43
1991 measured reflectionsk = 137
1140 independent reflectionsl = 1818
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)] = 0.073H 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 reflectionsΔρmax = 0.18 e Å3
112 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.019 (9)
Crystal data top
C6H5NO3V = 617.6 (3) Å3
Mr = 139.11Z = 4
Monoclinic, P21/nMo Kα radiation
a = 3.774 (1) ŵ = 0.12 mm1
b = 11.147 (4) ÅT = 293 K
c = 14.695 (3) Å0.82 × 0.36 × 0.25 mm
β = 92.60 (2)°
Data collection top
KUMA Diffraction KM4CCD
diffractometer
830 reflections with I > 2σ(I)
1991 measured reflectionsRint = 0.041
1140 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0730 restraints
wR(F2) = 0.201H atoms treated by a mixture of independent and constrained refinement
S = 1.19Δρmax = 0.18 e Å3
1140 reflectionsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
N0.2005 (9)0.7396 (3)0.4939 (2)0.0596 (10)
O10.0815 (9)0.5394 (3)0.16181 (19)0.0673 (9)
O20.3609 (9)0.6775 (3)0.5476 (2)0.0825 (12)
O30.1121 (11)0.8431 (3)0.5113 (2)0.0904 (13)
C10.0170 (9)0.5939 (3)0.2415 (2)0.0457 (9)
C20.0906 (10)0.7138 (4)0.2589 (3)0.0484 (10)
C30.0213 (10)0.7617 (4)0.3423 (3)0.0506 (10)
C40.1185 (9)0.6892 (3)0.4068 (2)0.0442 (9)
C50.1907 (9)0.5698 (4)0.3903 (2)0.0471 (9)
C60.1206 (10)0.5218 (4)0.3078 (3)0.0497 (10)
H10.137 (13)0.597 (5)0.125 (4)0.083 (17)*
H20.182 (11)0.761 (4)0.212 (3)0.066 (12)*
H30.051 (11)0.841 (4)0.358 (3)0.068 (13)*
H50.288 (11)0.523 (4)0.438 (3)0.068 (12)*
H60.171 (9)0.440 (4)0.294 (2)0.050 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.066 (2)0.062 (2)0.0507 (18)0.0028 (17)0.0054 (15)0.0015 (18)
O10.092 (2)0.063 (2)0.0484 (16)0.0086 (17)0.0151 (15)0.0021 (16)
O20.109 (3)0.089 (3)0.0517 (17)0.016 (2)0.0277 (17)0.0048 (17)
O30.130 (3)0.070 (2)0.073 (2)0.018 (2)0.028 (2)0.0190 (19)
C10.051 (2)0.046 (2)0.0411 (18)0.0051 (15)0.0032 (14)0.0031 (17)
C20.053 (2)0.046 (2)0.0465 (19)0.0006 (17)0.0102 (15)0.0088 (18)
C30.056 (2)0.045 (2)0.050 (2)0.0040 (17)0.0036 (16)0.0026 (19)
C40.0436 (18)0.051 (2)0.0379 (17)0.0010 (15)0.0036 (13)0.0014 (17)
C50.0454 (19)0.052 (2)0.0438 (18)0.0031 (16)0.0068 (14)0.0099 (18)
C60.053 (2)0.041 (2)0.055 (2)0.0034 (16)0.0016 (16)0.0001 (19)
Geometric parameters (Å, º) top
N—O31.224 (4)C1—C21.386 (5)
N—O21.230 (4)C2—C31.373 (5)
N—C41.445 (5)C3—C41.370 (5)
O1—C11.351 (4)C4—C51.377 (5)
C1—C61.383 (5)C5—C61.362 (5)
O3—N—O2122.3 (4)C4—C3—C2118.8 (4)
O3—N—C4119.0 (3)C3—C4—C5121.9 (3)
O2—N—C4118.7 (3)C3—C4—N119.2 (3)
O1—C1—C6116.0 (3)C5—C4—N118.9 (3)
O1—C1—C2123.5 (3)C6—C5—C4119.4 (3)
C6—C1—C2120.5 (3)C5—C6—C1119.6 (4)
C3—C2—C1119.8 (4)
(be120_9) 4-nitrophenol top
Crystal data top
C6H5NO3Dx = 1.550 Mg m3
Mr = 139.11Melting point: 384 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 3.678 (1) ÅCell parameters from 796 reflections
b = 11.091 (2) Åθ = 3.9–25.3°
c = 14.627 (3) ŵ = 0.13 mm1
β = 92.75 (3)°T = 120 K
V = 596.0 (2) Å3Needle, pale yellow
Z = 40.57 × 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 tubeRint = 0.015
Graphite monochromatorθmax = 27.3°, θmin = 4.6°
ω scanh = 42
2008 measured reflectionsk = 1312
1018 independent reflectionsl = 1417
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)] = 0.038H 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 reflectionsΔρmax = 0.20 e Å3
96 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.015 (6)
Crystal data top
C6H5NO3V = 596.0 (2) Å3
Mr = 139.11Z = 4
Monoclinic, P21/nMo Kα radiation
a = 3.678 (1) ŵ = 0.13 mm1
b = 11.091 (2) ÅT = 120 K
c = 14.627 (3) Å0.57 × 0.55 × 0.53 mm
β = 92.75 (3)°
Data collection top
KUMA Diffraction KM4CCD
diffractometer
913 reflections with I > 2σ(I)
2008 measured reflectionsRint = 0.015
1018 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.20 e Å3
1018 reflectionsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
N0.1913 (3)0.73628 (11)0.99181 (11)0.0221 (4)
O10.0874 (3)0.53655 (10)0.65552 (9)0.0254 (3)
O20.3612 (3)0.67489 (10)1.04568 (9)0.0301 (4)
O30.0904 (3)0.83991 (10)1.01088 (9)0.0326 (4)
C10.0267 (4)0.58952 (13)0.73624 (12)0.0190 (4)
C20.1057 (4)0.71058 (12)0.75491 (12)0.0201 (4)
H20.20540.75970.70920.024*
C30.0400 (4)0.75890 (12)0.83899 (12)0.0197 (4)
H30.09470.84100.85200.024*
C40.1078 (4)0.68561 (12)0.90484 (12)0.0183 (4)
C50.1877 (4)0.56465 (12)0.88775 (12)0.0192 (4)
H50.28840.51580.93350.023*
C60.1185 (4)0.51738 (12)0.80379 (12)0.0197 (4)
H60.16970.43490.79140.024*
H10.183 (6)0.585 (2)0.6176 (17)0.046 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0227 (7)0.0205 (6)0.0232 (11)0.0011 (5)0.0016 (6)0.0001 (5)
O10.0345 (7)0.0212 (6)0.0210 (9)0.0016 (4)0.0066 (5)0.0012 (4)
O20.0393 (7)0.0304 (6)0.0212 (9)0.0060 (5)0.0085 (6)0.0011 (5)
O30.0448 (7)0.0239 (6)0.0299 (10)0.0080 (5)0.0096 (6)0.0080 (5)
C10.0175 (7)0.0210 (7)0.0184 (11)0.0039 (5)0.0004 (6)0.0007 (6)
C20.0190 (7)0.0191 (7)0.0222 (11)0.0011 (5)0.0023 (6)0.0040 (6)
C30.0193 (7)0.0162 (6)0.0235 (12)0.0004 (5)0.0004 (6)0.0008 (5)
C40.0166 (7)0.0199 (7)0.0182 (11)0.0008 (5)0.0001 (6)0.0008 (6)
C50.0165 (7)0.0190 (7)0.0221 (12)0.0012 (5)0.0002 (6)0.0032 (5)
C60.0184 (7)0.0155 (6)0.0251 (12)0.0004 (5)0.0001 (7)0.0007 (6)
Geometric parameters (Å, º) top
N—O21.2337 (17)C1—C21.398 (2)
N—O31.2356 (17)C2—C31.374 (2)
N—C41.437 (2)C3—C41.391 (2)
O1—C11.347 (2)C4—C51.393 (2)
C1—C61.397 (2)C5—C61.370 (2)
O2—N—O3121.66 (15)C2—C3—C4118.91 (13)
O2—N—C4119.06 (12)C3—C4—C5121.64 (15)
O3—N—C4119.27 (13)C3—C4—N119.45 (13)
O1—C1—C6117.07 (13)C5—C4—N118.88 (13)
O1—C1—C2123.26 (14)C6—C5—C4118.85 (14)
C6—C1—C2119.66 (15)C5—C6—C1120.56 (13)
C3—C2—C1120.38 (14)
(pnif3754) 4-nitrophenol top
Crystal data top
C6H5NO3Dx = 1.468 Mg m3
Mr = 139.11Melting point: 384K K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 3.831 (1) ÅCell parameters from 1153 reflections
b = 11.093 (2) Åθ = 3.6–22.9°
c = 14.835 (3) ŵ = 0.12 mm1
β = 93.45 (3)°T = 375 K
V = 629.3 (2) Å3Needle, pale yellow
Z = 40.98 × 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 tubeRint = 0.061
Graphite monochromatorθmax = 31.4°, θmin = 5.4°
ω scanh = 25
4985 measured reflectionsk = 1616
1955 independent reflectionsl = 2121
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)] = 0.078H 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 reflectionsΔρmax = 0.26 e Å3
112 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.05 (3)
Crystal data top
C6H5NO3V = 629.3 (2) Å3
Mr = 139.11Z = 4
Monoclinic, P21/nMo Kα radiation
a = 3.831 (1) ŵ = 0.12 mm1
b = 11.093 (2) ÅT = 375 K
c = 14.835 (3) Å0.98 × 0.53 × 0.45 mm
β = 93.45 (3)°
Data collection top
KUMA Diffraction KM4CCD
diffractometer
1165 reflections with I > 2σ(I)
4985 measured reflectionsRint = 0.061
1955 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0780 restraints
wR(F2) = 0.294H atoms treated by a mixture of independent and constrained refinement
S = 1.16Δρmax = 0.26 e Å3
1955 reflectionsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
N0.2067 (6)0.2435 (2)0.99594 (14)0.0797 (7)
O10.0736 (6)0.04282 (18)0.66656 (13)0.0886 (6)
O20.3598 (7)0.1803 (2)1.04908 (14)0.1116 (9)
O30.1235 (9)0.3468 (2)1.01367 (19)0.1251 (10)
C10.0112 (5)0.0971 (2)0.74600 (14)0.0616 (6)
C20.0792 (6)0.2171 (2)0.76264 (15)0.0649 (6)
C30.0117 (6)0.2663 (2)0.84548 (15)0.0667 (6)
C40.1259 (5)0.19319 (19)0.90950 (14)0.0599 (5)
C50.1928 (5)0.0730 (2)0.89397 (15)0.0632 (6)
C60.1233 (6)0.0251 (2)0.81166 (17)0.0666 (6)
H50.281 (7)0.026 (3)0.944 (2)0.083 (8)*
H60.175 (8)0.065 (3)0.802 (2)0.094 (8)*
H30.070 (7)0.350 (3)0.866 (2)0.088 (8)*
H20.168 (8)0.264 (3)0.719 (2)0.089 (8)*
H10.169 (11)0.104 (5)0.625 (3)0.144 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0944 (14)0.0850 (15)0.0603 (11)0.0058 (11)0.0089 (9)0.0033 (10)
O10.1260 (15)0.0761 (12)0.0660 (11)0.0092 (10)0.0234 (10)0.0051 (8)
O20.154 (2)0.1214 (18)0.0629 (11)0.0072 (14)0.0372 (12)0.0049 (11)
O30.184 (3)0.0986 (17)0.0956 (17)0.0173 (16)0.0327 (16)0.0314 (13)
C10.0640 (11)0.0642 (11)0.0570 (11)0.0077 (8)0.0066 (8)0.0024 (9)
C20.0740 (12)0.0618 (12)0.0603 (12)0.0023 (9)0.0141 (9)0.0131 (9)
C30.0770 (13)0.0547 (11)0.0684 (13)0.0026 (9)0.0056 (10)0.0066 (9)
C40.0617 (10)0.0678 (12)0.0507 (10)0.0039 (9)0.0058 (8)0.0030 (8)
C50.0663 (11)0.0657 (12)0.0577 (11)0.0056 (8)0.0043 (8)0.0130 (9)
C60.0745 (12)0.0578 (11)0.0675 (13)0.0043 (9)0.0057 (9)0.0034 (9)
Geometric parameters (Å, º) top
N—O31.215 (3)C1—C61.383 (3)
N—O21.230 (3)C2—C31.383 (3)
N—C41.449 (3)C3—C41.378 (3)
O1—C11.357 (3)C4—C51.374 (3)
C1—C21.376 (3)C5—C61.373 (3)
O3—N—O2121.9 (2)C4—C3—C2118.7 (2)
O3—N—C4119.2 (2)C5—C4—C3122.1 (2)
O2—N—C4118.9 (2)C5—C4—N118.31 (19)
O1—C1—C2122.92 (19)C3—C4—N119.6 (2)
O1—C1—C6116.6 (2)C6—C5—C4118.74 (18)
C2—C1—C6120.5 (2)C5—C6—C1120.2 (2)
C1—C2—C3119.87 (18)

Experimental details

(alfa_6)(al120_5)(al333_5)(betdc6)
Crystal data
Chemical formulaC6H5NO3C6H5NO3C6H5NO3C6H5NO3
Mr139.11139.11139.11139.11
Crystal system, space groupMonoclinic, P21/c?Monoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/n
Temperature (K)298120333293
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)
V3)620.9 (4)603.1 (2)626.9 (3)617.6 (3)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.120.130.120.12
Crystal size (mm)0.77 × 0.38 × 0.380.79 × 0.55 × 0.500.79 × 0.55 × 0.500.82 × 0.36 × 0.25
Data collection
DiffractometerKUMA 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
Rint0.0390.0460.0290.041
(sin θ/λ)max1)0.6470.6400.6480.643
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 reflections1197101910671140
No. of parameters96112112112
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.130.21, 0.210.16, 0.120.18, 0.18


(be120_9)(pnif3754)
Crystal data
Chemical formulaC6H5NO3C6H5NO3
Mr139.11139.11
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)120375
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)
V3)596.0 (2)629.3 (2)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.130.12
Crystal size (mm)0.57 × 0.55 × 0.530.98 × 0.53 × 0.45
Data collection
DiffractometerKUMA 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
Rint0.0150.061
(sin θ/λ)max1)0.6450.732
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.104, 1.05 0.078, 0.294, 1.16
No. of reflections10181955
No. of parameters96112
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.270.26, 0.22

Computer programs: KUMA KM4CCD software, 1999, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds