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The title compound,
p-phenylenedimethanol, C
8H
10O
2, crystallizes in the space group
P2
1/
n and forms extensive supramolecular sheets parallel to (001)
via O—H
O hydrogen bonds. Sheets stack along the
c axis
via weak C—H
O interactions. The molecule has no crystallographic symmetry.
Supporting information
CCDC reference: 177231
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.101
- Data-to-parameter ratio = 12.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced
by the scaled T values. Since the ratio of scaled T's is
identical to the ratio of reported T values, the scaling does
not imply a change to the absorption corrections used in the
study.
Ratio of Tmax expected/reported 1.084
Tmax scaled 0.995 Tmin scaled 0.965
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXL97.
1,4-Benzenedimethanol
top
Crystal data top
C8H10O2 | Dx = 1.289 Mg m−3 |
Mr = 138.16 | Melting point: not measured K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.8118 (3) Å | Cell parameters from 2696 reflections |
b = 15.4697 (14) Å | θ = 1.0–25.0° |
c = 9.7712 (8) Å | µ = 0.09 mm−1 |
β = 101.798 (5)° | T = 180 K |
V = 711.97 (10) Å3 | Needle, colourless |
Z = 4 | 0.46 × 0.10 × 0.05 mm |
F(000) = 296 | |
Data collection top
Nonius KappaCCD diffractometer | 1238 independent reflections |
Radiation source: fine-focus sealed tube | 974 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Thin–slice ω and φ scans | θmax = 25.0°, θmin = 4.4° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −5→5 |
Tmin = 0.890, Tmax = 0.918 | k = −18→18 |
4055 measured reflections | l = −9→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.1336P] where P = (Fo2 + 2Fc2)/3 |
1238 reflections | (Δ/σ)max < 0.001 |
99 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | |
H01 | −0.019 (5) | 0.3502 (16) | 0.758 (2) | 0.080 (7)* | |
O1 | 0.1431 (2) | 0.32039 (8) | 0.76067 (13) | 0.0436 (4) | |
H02 | 1.020 (5) | −0.1320 (15) | 0.754 (2) | 0.077 (7)* | |
O2 | 0.8633 (2) | −0.09855 (8) | 0.75766 (14) | 0.0438 (4) | |
C1 | 0.3407 (3) | 0.17742 (10) | 0.79918 (15) | 0.0272 (4) | |
C3 | 0.6625 (3) | 0.05778 (10) | 0.86612 (16) | 0.0312 (4) | |
H3 | 0.7582 | 0.0200 | 0.9369 | 0.037* | |
C2 | 0.4853 (3) | 0.12122 (10) | 0.90003 (16) | 0.0311 (4) | |
H2 | 0.4621 | 0.1264 | 0.9939 | 0.037* | |
C5 | 0.5595 (3) | 0.10499 (10) | 0.62968 (16) | 0.0323 (4) | |
H5 | 0.5845 | 0.1000 | 0.5361 | 0.039* | |
C6 | 0.3807 (3) | 0.16856 (10) | 0.66313 (16) | 0.0321 (4) | |
H6 | 0.2850 | 0.2063 | 0.5923 | 0.038* | |
C8 | 0.9023 (3) | −0.01801 (10) | 0.69371 (18) | 0.0346 (4) | |
H8A | 0.8671 | −0.0253 | 0.5909 | 0.041* | |
H8B | 1.1007 | 0.0017 | 0.7259 | 0.041* | |
C7 | 0.1413 (3) | 0.24332 (10) | 0.83848 (17) | 0.0345 (4) | |
H7A | −0.0535 | 0.2193 | 0.8209 | 0.041* | |
H7B | 0.1984 | 0.2564 | 0.9395 | 0.041* | |
C4 | 0.7023 (3) | 0.04866 (10) | 0.73057 (16) | 0.0269 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0344 (7) | 0.0259 (7) | 0.0756 (9) | 0.0051 (5) | 0.0235 (6) | 0.0121 (6) |
O2 | 0.0329 (7) | 0.0234 (7) | 0.0796 (9) | 0.0010 (5) | 0.0222 (6) | 0.0013 (6) |
C1 | 0.0237 (7) | 0.0219 (9) | 0.0371 (9) | −0.0045 (6) | 0.0086 (6) | −0.0014 (7) |
C3 | 0.0293 (8) | 0.0296 (9) | 0.0338 (9) | 0.0012 (7) | 0.0046 (7) | 0.0055 (7) |
C2 | 0.0344 (9) | 0.0309 (10) | 0.0297 (8) | −0.0019 (7) | 0.0105 (7) | 0.0006 (7) |
C5 | 0.0360 (9) | 0.0316 (9) | 0.0313 (9) | −0.0020 (7) | 0.0113 (7) | −0.0004 (7) |
C6 | 0.0346 (9) | 0.0284 (9) | 0.0330 (9) | 0.0026 (7) | 0.0063 (7) | 0.0059 (7) |
C8 | 0.0301 (8) | 0.0265 (10) | 0.0494 (10) | −0.0038 (7) | 0.0136 (8) | −0.0018 (8) |
C7 | 0.0352 (9) | 0.0263 (9) | 0.0445 (10) | −0.0006 (7) | 0.0144 (7) | 0.0009 (8) |
C4 | 0.0221 (8) | 0.0224 (9) | 0.0373 (9) | −0.0055 (6) | 0.0084 (7) | −0.0013 (7) |
Geometric parameters (Å, º) top
O1—C7 | 1.4150 (19) | C2—H2 | 0.950 |
O1—H01 | 0.90 (3) | C5—C4 | 1.388 (2) |
O2—C8 | 1.4233 (19) | C5—C6 | 1.389 (2) |
O2—H02 | 0.92 (2) | C5—H5 | 0.950 |
C1—C6 | 1.388 (2) | C6—H6 | 0.950 |
C1—C2 | 1.389 (2) | C8—C4 | 1.504 (2) |
C1—C7 | 1.503 (2) | C8—H8A | 0.990 |
C3—C4 | 1.384 (2) | C8—H8B | 0.990 |
C3—C2 | 1.384 (2) | C7—H7A | 0.990 |
C3—H3 | 0.950 | C7—H7B | 0.990 |
| | | |
C7—O1—H01 | 110.4 (15) | C5—C6—H6 | 119.7 |
C8—O2—H02 | 107.0 (14) | O2—C8—C4 | 110.29 (13) |
C6—C1—C2 | 118.03 (14) | O2—C8—H8A | 109.6 |
C6—C1—C7 | 122.17 (14) | C4—C8—H8A | 109.6 |
C2—C1—C7 | 119.77 (14) | O2—C8—H8B | 109.6 |
C4—C3—C2 | 120.93 (14) | C4—C8—H8B | 109.6 |
C4—C3—H3 | 119.5 | H8A—C8—H8B | 108.1 |
C2—C3—H3 | 119.5 | O1—C7—C1 | 111.09 (13) |
C3—C2—C1 | 121.17 (14) | O1—C7—H7A | 109.4 |
C3—C2—H2 | 119.4 | C1—C7—H7A | 109.4 |
C1—C2—H2 | 119.4 | O1—C7—H7B | 109.4 |
C4—C5—C6 | 121.19 (14) | C1—C7—H7B | 109.4 |
C4—C5—H5 | 119.4 | H7A—C7—H7B | 108.0 |
C6—C5—H5 | 119.4 | C3—C4—C5 | 118.07 (14) |
C1—C6—C5 | 120.60 (14) | C3—C4—C8 | 121.31 (14) |
C1—C6—H6 | 119.7 | C5—C4—C8 | 120.57 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H01···O2i | 0.90 (3) | 1.82 (3) | 2.7138 (15) | 174 (2) |
O2—H02···O1ii | 0.92 (2) | 1.81 (3) | 2.7238 (14) | 170 (2) |
C2—H2···O1iii | 0.95 | 2.70 | 3.566 (2) | 152 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x+1/2, −y+1/2, z+1/2. |
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