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In the title compound, C6H7NO·C18H20O2, the host mol­ecules of 1,1-bis­(4-hydroxy­phen­yl)cyclo­hexane are hydrogen bonded via the hydr­oxy groups into zigzag chains extended along the a axis. The guest mol­ecules of 4-methyl-2-pyridone are paired into N—H...O hydrogen-bonded dimers, which connect two zigzag chains via O—H...O hydrogen bonds to produce a hydrogen-bonded ribbon. Structure analysis reveals that the mutual relation between two successive guest mol­ecules does not enable photodimerization.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032764/cv2100sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032764/cv2100Isup2.hkl
Contains datablock I

CCDC reference: 620950

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.046
  • wR factor = 0.127
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
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

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

4-methyl-2-pyridone–1,1'-bis(4-hydroxyphenyl)cyclohexane (1/1) top
Crystal data top
C6H7NO·C18H20O2F(000) = 808
Mr = 377.47Dx = 1.227 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2 ybcCell parameters from 16251 reflections
a = 10.931 (2) Åθ = 2.2–27.8°
b = 16.737 (3) ŵ = 0.08 mm1
c = 11.340 (2) ÅT = 293 K
β = 99.93 (3)°Prism, colourless
V = 2043.6 (7) Å30.30 × 0.25 × 0.10 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2609 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
Graphite monochromatorθmax = 27.8°, θmin = 2.2°
CCD scansh = 014
16251 measured reflectionsk = 021
4630 independent reflectionsl = 1414
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0675P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.013
4630 reflectionsΔρmax = 0.19 e Å3
258 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.038 (4)
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
O10.67506 (10)0.29365 (8)0.11291 (11)0.0537 (3)
H1O10.65650.33050.06550.085 (8)*
O20.11016 (12)0.28529 (9)0.28656 (12)0.0740 (5)
H2O20.17310.28980.23590.091 (8)*
O30.39622 (10)0.07726 (8)0.50974 (10)0.0534 (3)
N10.37396 (13)0.04843 (9)0.57422 (11)0.0502 (4)
H1N10.44370.06020.55310.056 (5)*
C10.25589 (13)0.08859 (10)0.12277 (12)0.0378 (4)
C20.20847 (14)0.04930 (11)0.00033 (12)0.0447 (4)
H2A0.13030.02260.00250.054*
H2B0.19300.09070.06100.054*
C30.29964 (17)0.01085 (12)0.03608 (14)0.0567 (5)
H3A0.26520.03370.11330.068*
H3B0.37630.01620.04380.068*
C40.32718 (19)0.07724 (13)0.05599 (16)0.0656 (6)
H4A0.25220.10780.05800.079*
H4B0.38900.11300.03340.079*
C50.37453 (17)0.04284 (11)0.17898 (14)0.0541 (5)
H5A0.45490.01820.17940.065*
H5B0.38520.08560.23760.065*
C60.28472 (14)0.01906 (10)0.21350 (13)0.0448 (4)
H6A0.31960.04100.29120.054*
H6B0.20750.00740.22110.054*
C70.37045 (13)0.14119 (9)0.11785 (12)0.0361 (4)
C80.47037 (14)0.14595 (11)0.21176 (12)0.0450 (4)
H80.47040.11360.27850.054*
C90.56995 (15)0.19686 (11)0.21009 (13)0.0488 (4)
H90.63460.19850.27520.059*
C100.57349 (13)0.24501 (10)0.11221 (13)0.0398 (4)
C110.47644 (14)0.24164 (10)0.01648 (13)0.0430 (4)
H110.47770.27360.05040.052*
C120.37732 (14)0.19062 (10)0.02010 (12)0.0402 (4)
H120.31280.18930.04520.048*
C130.15512 (13)0.14233 (9)0.16182 (12)0.0371 (4)
C140.04262 (14)0.15908 (11)0.08980 (13)0.0444 (4)
H140.02630.13780.01290.053*
C150.04692 (14)0.20673 (11)0.12854 (14)0.0507 (5)
H150.12120.21750.07750.061*
C160.02537 (14)0.23776 (11)0.24236 (16)0.0496 (4)
C170.08593 (14)0.22199 (12)0.31695 (14)0.0515 (5)
H170.10100.24250.39440.062*
C180.17430 (15)0.17595 (11)0.27635 (14)0.0471 (4)
H180.24950.16690.32690.057*
C190.33096 (14)0.02722 (11)0.55590 (12)0.0433 (4)
C200.21559 (15)0.04351 (11)0.59158 (13)0.0483 (4)
H200.18250.09470.58140.058*
C210.15153 (15)0.01435 (12)0.64076 (13)0.0490 (5)
C220.20248 (17)0.09161 (12)0.65671 (16)0.0602 (5)
H220.16020.13190.68950.072*
C230.31307 (18)0.10677 (12)0.62405 (16)0.0619 (5)
H230.34790.15750.63570.074*
C240.02966 (17)0.00367 (15)0.68005 (16)0.0721 (6)
H24A0.02620.04040.65960.108*
H24B0.04330.01180.76510.108*
H24C0.00580.05110.64040.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0343 (6)0.0486 (8)0.0768 (8)0.0020 (6)0.0060 (5)0.0090 (7)
O20.0441 (8)0.0915 (12)0.0845 (9)0.0187 (7)0.0054 (7)0.0343 (8)
O30.0473 (7)0.0516 (8)0.0628 (7)0.0029 (6)0.0135 (5)0.0075 (6)
N10.0447 (8)0.0509 (10)0.0589 (8)0.0061 (7)0.0201 (7)0.0027 (7)
C10.0340 (8)0.0427 (10)0.0369 (7)0.0031 (7)0.0072 (6)0.0009 (7)
C20.0396 (9)0.0482 (11)0.0457 (8)0.0033 (8)0.0058 (7)0.0069 (8)
C30.0533 (11)0.0652 (14)0.0514 (9)0.0081 (10)0.0086 (8)0.0176 (9)
C40.0651 (13)0.0523 (14)0.0787 (13)0.0140 (10)0.0106 (10)0.0155 (10)
C50.0530 (10)0.0464 (12)0.0634 (10)0.0098 (9)0.0118 (8)0.0058 (9)
C60.0417 (9)0.0445 (11)0.0504 (9)0.0010 (8)0.0139 (7)0.0053 (8)
C70.0307 (8)0.0418 (10)0.0369 (7)0.0033 (7)0.0087 (6)0.0003 (7)
C80.0408 (9)0.0558 (12)0.0373 (8)0.0016 (8)0.0033 (7)0.0075 (7)
C90.0368 (9)0.0603 (13)0.0464 (9)0.0011 (8)0.0009 (7)0.0015 (8)
C100.0297 (8)0.0370 (10)0.0543 (9)0.0039 (7)0.0115 (7)0.0010 (7)
C110.0389 (9)0.0461 (11)0.0447 (8)0.0052 (8)0.0094 (7)0.0077 (7)
C120.0338 (8)0.0458 (11)0.0393 (8)0.0038 (7)0.0013 (6)0.0029 (7)
C130.0332 (8)0.0389 (10)0.0397 (8)0.0013 (7)0.0075 (6)0.0001 (7)
C140.0391 (9)0.0542 (12)0.0392 (8)0.0024 (8)0.0044 (7)0.0027 (8)
C150.0341 (9)0.0590 (13)0.0565 (10)0.0076 (8)0.0009 (7)0.0034 (9)
C160.0358 (9)0.0511 (12)0.0628 (10)0.0032 (8)0.0114 (7)0.0146 (9)
C170.0383 (9)0.0629 (13)0.0524 (10)0.0037 (8)0.0056 (7)0.0167 (9)
C180.0322 (8)0.0569 (12)0.0499 (9)0.0020 (8)0.0006 (7)0.0096 (8)
C190.0415 (9)0.0464 (12)0.0406 (8)0.0013 (8)0.0035 (7)0.0014 (7)
C200.0427 (9)0.0486 (12)0.0528 (9)0.0064 (8)0.0059 (7)0.0041 (8)
C210.0426 (9)0.0573 (13)0.0478 (9)0.0009 (9)0.0099 (7)0.0081 (8)
C220.0633 (12)0.0541 (13)0.0699 (11)0.0076 (10)0.0301 (9)0.0020 (10)
C230.0692 (13)0.0466 (12)0.0777 (12)0.0027 (10)0.0344 (10)0.0023 (10)
C240.0477 (11)0.0938 (18)0.0786 (13)0.0024 (11)0.0217 (10)0.0079 (12)
Geometric parameters (Å, º) top
O1—C101.3757 (18)C8—H80.9300
O1—H1O10.8200C9—C101.378 (2)
O2—C161.3797 (19)C9—H90.9300
O2—H2O20.8200C10—C111.382 (2)
O3—C191.2702 (19)C11—C121.386 (2)
N1—C191.354 (2)C11—H110.9300
N1—C231.358 (2)C12—H120.9300
N1—H1N10.8600C13—C141.383 (2)
C1—C71.540 (2)C13—C181.398 (2)
C1—C131.545 (2)C14—C151.391 (2)
C1—C21.549 (2)C14—H140.9300
C1—C61.549 (2)C15—C161.373 (2)
C2—C31.520 (2)C15—H150.9300
C2—H2A0.9700C16—C171.382 (2)
C2—H2B0.9700C17—C181.376 (2)
C3—C41.519 (3)C17—H170.9300
C3—H3A0.9700C18—H180.9300
C3—H3B0.9700C19—C201.416 (2)
C4—C51.515 (2)C20—C211.369 (2)
C4—H4A0.9700C20—H200.9300
C4—H4B0.9700C21—C221.407 (3)
C5—C61.524 (2)C21—C241.506 (2)
C5—H5A0.9700C22—C231.348 (2)
C5—H5B0.9700C22—H220.9300
C6—H6A0.9700C23—H230.9300
C6—H6B0.9700C24—H24A0.9600
C7—C81.390 (2)C24—H24B0.9600
C7—C121.396 (2)C24—H24C0.9600
C8—C91.385 (2)
C10—O1—H1O1109.5C9—C10—C11118.99 (15)
C16—O2—H2O2109.5C10—C11—C12120.01 (14)
C7—C1—C13107.58 (13)C10—C11—H11120.0
C7—C1—C2110.98 (11)C12—C11—H11120.0
C13—C1—C2111.17 (12)C11—C12—C7122.57 (14)
C7—C1—C6112.33 (12)C11—C12—H12118.7
C13—C1—C6108.69 (11)C7—C12—H12118.7
C2—C1—C6106.12 (14)C14—C13—C18116.29 (14)
C3—C2—C1112.86 (13)C14—C13—C1123.66 (13)
C3—C2—H2A109.0C18—C13—C1120.05 (13)
C1—C2—H2A109.0C13—C14—C15122.15 (14)
C3—C2—H2B109.0C13—C14—H14118.9
C1—C2—H2B109.0C15—C14—H14118.9
H2A—C2—H2B107.8C16—C15—C14119.84 (15)
C4—C3—C2111.25 (13)C16—C15—H15120.1
C4—C3—H3A109.4C14—C15—H15120.1
C2—C3—H3A109.4C15—C16—O2122.85 (15)
C4—C3—H3B109.4C15—C16—C17119.55 (15)
C2—C3—H3B109.4O2—C16—C17117.60 (15)
H3A—C3—H3B108.0C18—C17—C16119.80 (15)
C5—C4—C3110.52 (16)C18—C17—H17120.1
C5—C4—H4A109.5C16—C17—H17120.1
C3—C4—H4A109.5C17—C18—C13122.35 (15)
C5—C4—H4B109.5C17—C18—H18118.8
C3—C4—H4B109.5C13—C18—H18118.8
H4A—C4—H4B108.1C19—N1—C23123.64 (15)
C4—C5—C6111.21 (15)C19—N1—H1N1118.2
C4—C5—H5A109.4C23—N1—H1N1118.2
C6—C5—H5A109.4O3—C19—N1118.36 (14)
C4—C5—H5B109.4O3—C19—C20125.60 (17)
C6—C5—H5B109.4N1—C19—C20116.03 (16)
H5A—C5—H5B108.0C21—C20—C19121.58 (17)
C5—C6—C1113.97 (12)C21—C20—H20119.2
C5—C6—H6A108.8C19—C20—H20119.2
C1—C6—H6A108.8C20—C21—C22118.91 (16)
C5—C6—H6B108.8C20—C21—C24121.30 (18)
C1—C6—H6B108.8C22—C21—C24119.78 (17)
H6A—C6—H6B107.7C23—C22—C21119.43 (17)
C8—C7—C12115.58 (14)C23—C22—H22120.3
C8—C7—C1122.79 (13)C21—C22—H22120.3
C12—C7—C1121.55 (13)C22—C23—N1120.39 (18)
C9—C8—C7122.71 (14)C22—C23—H23119.8
C9—C8—H8118.6N1—C23—H23119.8
C7—C8—H8118.6C21—C24—H24A109.5
C10—C9—C8120.15 (14)C21—C24—H24B109.5
C10—C9—H9119.9H24A—C24—H24B109.5
C8—C9—H9119.9C21—C24—H24C109.5
O1—C10—C9118.45 (14)H24A—C24—H24C109.5
O1—C10—C11122.55 (14)H24B—C24—H24C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O3i0.821.812.615 (2)167
O2—H2O2···O1ii0.821.982.796 (2)177
N1—H1N1···O3iii0.862.022.877 (2)173
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x1, y, z; (iii) x+1, y, z+1.
 

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