In the title compound, C
6H
6O
2·2C
5H
5NO, there is one pyridin-4-ol and half a hydroquinone molecule in the asymmetric unit; the hydroquinone molecule lies on an inversion center. The crystal structure is stabilized by intermolecular O—H
N and O—H
O hydrogen bonds, building a corrugated two-dimensional network.
Supporting information
CCDC reference: 633675
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.142
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C5 H5 N O
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
Pyridin-4-ol–hydroquinone (2/1)
top
Crystal data top
C6H6O2·2C5H5NO | F(000) = 316 |
Mr = 300.31 | Dx = 1.373 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9050 reflections |
a = 6.2244 (6) Å | θ = 2.4–27.2° |
b = 17.3662 (15) Å | µ = 0.10 mm−1 |
c = 7.1342 (8) Å | T = 293 K |
β = 109.585 (8)° | Prism, yellow |
V = 726.55 (12) Å3 | 0.34 × 0.25 × 0.20 mm |
Z = 2 | |
Data collection top
Stoe IPDS-2 diffractometer | 1432 independent reflections |
Radiation source: fine-focus sealed tube | 1154 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −7→7 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −21→21 |
Tmin = 0.941, Tmax = 0.973 | l = −8→8 |
6697 measured reflections | |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0828P)2 + 0.156P] where P = (Fo2 + 2Fc2)/3 |
1432 reflections | (Δ/σ)max < 0.001 |
102 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.43 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 | |
C6 | 0.5805 (3) | 0.48138 (9) | 0.3445 (3) | 0.0425 (5) | |
C7 | 0.3648 (3) | 0.45832 (10) | 0.3401 (3) | 0.0460 (5) | |
H7 | 0.2722 | 0.4303 | 0.2322 | 0.055* | |
C8 | 0.2874 (3) | 0.47650 (10) | 0.4931 (3) | 0.0473 (5) | |
H8 | 0.1432 | 0.4602 | 0.4878 | 0.057* | |
O2 | 0.6676 (2) | 0.46301 (8) | 0.1979 (2) | 0.0544 (4) | |
H2 | 0.5835 | 0.4319 | 0.1216 | 0.082* | |
C1 | 0.2430 (3) | 0.31108 (10) | −0.0830 (3) | 0.0404 (4) | |
C2 | 0.1893 (3) | 0.23122 (10) | −0.1067 (3) | 0.0468 (5) | |
H2A | 0.3039 | 0.1952 | −0.0524 | 0.056* | |
C3 | −0.0237 (3) | 0.20664 (11) | −0.2062 (3) | 0.0470 (5) | |
H3 | −0.0523 | 0.1540 | −0.2202 | 0.056* | |
C4 | −0.1554 (3) | 0.33292 (11) | −0.2645 (3) | 0.0497 (5) | |
H4 | −0.2758 | 0.3670 | −0.3176 | 0.060* | |
C5 | 0.0555 (3) | 0.36142 (10) | −0.1680 (3) | 0.0459 (5) | |
H5 | 0.0777 | 0.4144 | −0.1572 | 0.055* | |
N1 | −0.1960 (3) | 0.25625 (9) | −0.2858 (3) | 0.0475 (4) | |
O1 | 0.4425 (2) | 0.33497 (7) | 0.0078 (2) | 0.0545 (4) | |
H1 | 0.5286 | 0.2981 | 0.0448 | 0.082* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C6 | 0.0402 (9) | 0.0292 (8) | 0.0540 (12) | 0.0019 (6) | 0.0104 (8) | 0.0019 (7) |
C7 | 0.0375 (9) | 0.0368 (9) | 0.0548 (12) | −0.0053 (7) | 0.0037 (8) | −0.0059 (8) |
C8 | 0.0355 (9) | 0.0382 (9) | 0.0631 (13) | −0.0062 (7) | 0.0097 (9) | −0.0061 (8) |
O2 | 0.0513 (8) | 0.0485 (8) | 0.0629 (10) | −0.0087 (6) | 0.0185 (7) | −0.0116 (6) |
C1 | 0.0371 (9) | 0.0377 (9) | 0.0410 (10) | −0.0002 (7) | 0.0060 (7) | −0.0039 (7) |
C2 | 0.0404 (9) | 0.0355 (9) | 0.0548 (12) | 0.0033 (7) | 0.0031 (8) | −0.0022 (8) |
C3 | 0.0443 (10) | 0.0375 (9) | 0.0509 (11) | −0.0017 (7) | 0.0050 (8) | −0.0005 (8) |
C4 | 0.0418 (10) | 0.0439 (10) | 0.0544 (12) | 0.0066 (8) | 0.0043 (9) | 0.0068 (8) |
C5 | 0.0459 (10) | 0.0343 (9) | 0.0504 (12) | 0.0016 (7) | 0.0067 (8) | 0.0013 (8) |
N1 | 0.0394 (8) | 0.0445 (9) | 0.0506 (10) | −0.0017 (6) | 0.0044 (7) | 0.0033 (7) |
O1 | 0.0367 (7) | 0.0399 (7) | 0.0715 (10) | 0.0000 (5) | −0.0022 (7) | −0.0073 (6) |
Geometric parameters (Å, º) top
C6—O2 | 1.367 (3) | C1—C2 | 1.423 (2) |
C6—C8i | 1.384 (3) | C2—C3 | 1.347 (2) |
C6—C7 | 1.391 (3) | C2—H2A | 0.9300 |
C7—C8 | 1.370 (3) | C3—N1 | 1.344 (2) |
C7—H7 | 0.9300 | C3—H3 | 0.9300 |
C8—C6i | 1.384 (3) | C4—N1 | 1.354 (3) |
C8—H8 | 0.9300 | C4—C5 | 1.355 (3) |
O2—H2 | 0.8200 | C4—H4 | 0.9300 |
C1—O1 | 1.262 (2) | C5—H5 | 0.9300 |
C1—C5 | 1.421 (2) | O1—H1 | 0.8200 |
| | | |
O2—C6—C8i | 119.14 (17) | C3—C2—H2A | 119.3 |
O2—C6—C7 | 122.87 (18) | C1—C2—H2A | 119.3 |
C8i—C6—C7 | 117.98 (19) | N1—C3—C2 | 121.65 (18) |
C8—C7—C6 | 120.68 (18) | N1—C3—H3 | 119.2 |
C8—C7—H7 | 119.7 | C2—C3—H3 | 119.2 |
C6—C7—H7 | 119.7 | N1—C4—C5 | 121.90 (17) |
C7—C8—C6i | 121.34 (17) | N1—C4—H4 | 119.1 |
C7—C8—H8 | 119.3 | C5—C4—H4 | 119.1 |
C6i—C8—H8 | 119.3 | C4—C5—C1 | 120.62 (17) |
C6—O2—H2 | 109.5 | C4—C5—H5 | 119.7 |
O1—C1—C5 | 122.86 (16) | C1—C5—H5 | 119.7 |
O1—C1—C2 | 122.18 (16) | C3—N1—C4 | 119.39 (16) |
C5—C1—C2 | 114.97 (16) | C1—O1—H1 | 109.5 |
C3—C2—C1 | 121.47 (17) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.82 | 1.94 | 2.7339 (19) | 161 |
O1—H1···N1ii | 0.82 | 1.98 | 2.743 (2) | 156 |
Symmetry code: (ii) x+1, −y+1/2, z+1/2. |