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Structure analysis of the title compound, C17H21NO2·H2O, containing a polar 4-pyridone moiety, demonstrates that bifurcated acceptor hydrogen bonds involving water mol­ecules as hydrogen-bonding donors and C=O groups as hydrogen-bonding acceptors form infinite one-dimensional mol­ecular chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010524/fl6156sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010524/fl6156Isup2.hkl
Contains datablock I

CCDC reference: 271875

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.071
  • wR factor = 0.280
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.26 Ratio
Author Response: The last three atoms of the side-chain are somewhat disordered. DFIX and DANG restraints were effective at improving the poor geometry (at the expense of much poorer R-factors). However the poor thermal displacements could not be improved by the use of SIMU, DELU, or even ISOR (or combinations thereof). Two afternoons were spent trying. The equipment for low-temperature data collection unfortunately does not exist at this facility
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.29 Ratio
Author Response: See previous response
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        C17
Author Response: See first response. Atom C17 appears to be the most disordered atom.

Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C16 - C17 .. 9.40 su PLAT731_ALERT_1_B Bond Calc 1.505(11), Rep 1.504(2) ...... 5.50 su-Rat C16 -C17 1.555 1.555
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.280 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT084_ALERT_2_C High R2 Value .................................. 0.28 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
Author Response: See first response. Atom C17 appears to be the most disordered atom.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT411_ALERT_2_C Short Inter H...H Contact  H12    ..  H17A    ..       2.14 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.84(5), Rep     0.85(2) ......       2.50 su-Rat
              O3   -H19A    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.82(5), Rep     0.82(2) ......       2.50 su-Rat
              O3   -H19B    1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

3 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek 2003); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON.

1-(4-(Hexyloxy)phenyl)pyridin-4(1H)-one monohydrate top
Crystal data top
C17H21NO2·H2OF(000) = 624
Mr = 289.36Dx = 1.169 Mg m3
Monoclinic, P21/cMelting point: 355.6 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71069 Å
a = 17.815 (5) ÅCell parameters from 25 reflections
b = 8.022 (3) Åθ = 10.0–11.0°
c = 12.251 (3) ŵ = 0.08 mm1
β = 110.09 (2)°T = 296 K
V = 1644.3 (9) Å3Plate, colorless
Z = 40.49 × 0.41 × 0.16 mm
Data collection top
Rigaku AFC-5S
diffractometer
Rint = 0.017
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.4°
Graphite monochromatorh = 2119
ω scansk = 90
3075 measured reflectionsl = 014
2923 independent reflections3 standard reflections every 100 reflections
1400 reflections with I > 2σ(I) intensity decay: 0.6%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.280H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.1703P)2 + 0.0959P]
where P = (Fo2 + 2Fc2)/3
2923 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.52 e Å3
6 restraintsΔρmin = 0.55 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.96070 (17)0.6274 (3)1.1453 (2)0.0570 (8)
O20.69011 (19)0.4240 (4)0.3275 (2)0.0789 (10)
O31.0719 (2)0.9003 (4)1.1981 (3)0.0743 (10)
N10.85177 (18)0.5276 (4)0.7993 (2)0.0473 (8)
C20.8411 (2)0.4264 (5)0.8826 (3)0.0546 (10)
C30.8757 (2)0.4570 (5)0.9959 (3)0.0542 (10)
C40.9266 (2)0.5978 (4)1.0384 (3)0.0471 (9)
C50.9360 (2)0.7007 (4)0.9493 (3)0.0497 (10)
C60.8994 (2)0.6637 (4)0.8350 (3)0.0470 (9)
C70.8122 (2)0.4951 (5)0.6775 (3)0.0488 (10)
C80.8540 (2)0.5059 (5)0.6019 (3)0.0510 (10)
C90.8148 (2)0.4832 (5)0.4837 (3)0.0546 (10)
C100.7342 (3)0.4467 (5)0.4430 (3)0.0583 (11)
C110.6930 (3)0.4320 (6)0.5195 (4)0.0694 (13)
C120.7324 (3)0.4543 (6)0.6353 (4)0.0687 (13)
C130.7189 (3)0.4995 (6)0.2434 (3)0.0686 (12)
C140.6508 (3)0.5004 (7)0.1281 (4)0.0879 (16)
C150.6724 (4)0.5708 (8)0.0315 (4)0.115 (2)
C160.5961 (5)0.5551 (13)0.0796 (6)0.181 (4)
C170.6111 (5)0.6146 (15)0.1868 (5)0.247 (8)
C180.5372 (4)0.5738 (12)0.2890 (5)0.160 (4)
H20.80860.33290.85940.066*
H30.86640.38431.04900.065*
H50.96790.79530.96980.060*
H60.90710.73390.77940.056*
H80.90850.52850.63000.061*
H90.84260.49250.43220.065*
H110.63870.40690.49220.083*
H120.70480.44180.68690.082*
H13A0.76370.43650.23700.082*
H13B0.73660.61250.26660.082*
H14A0.63210.38700.10860.106*
H14B0.60690.56460.13640.106*
H15A0.71650.50910.02170.138*
H15B0.68810.68660.04670.138*
H16A0.57920.43960.08990.217*
H16B0.55330.62020.06900.217*
H17A0.65730.55870.19430.296*
H17B0.62080.73380.18250.296*
H18A0.54760.59260.35990.240*
H18B0.49390.64370.28740.240*
H18C0.52320.45900.28490.240*
H19A1.042 (3)0.818 (5)1.196 (5)0.111*
H19B1.063 (4)0.963 (6)1.245 (4)0.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0796 (19)0.0502 (16)0.0403 (15)0.0005 (14)0.0193 (13)0.0059 (12)
O20.083 (2)0.100 (2)0.0444 (17)0.0225 (19)0.0097 (15)0.0030 (15)
O30.084 (2)0.080 (2)0.071 (2)0.0221 (17)0.0417 (18)0.0203 (17)
N10.0549 (18)0.0453 (18)0.0400 (17)0.0019 (15)0.0142 (14)0.0005 (13)
C20.070 (3)0.048 (2)0.046 (2)0.014 (2)0.0212 (19)0.0022 (17)
C30.072 (3)0.048 (2)0.047 (2)0.006 (2)0.0258 (19)0.0032 (17)
C40.060 (2)0.039 (2)0.044 (2)0.0062 (17)0.0203 (17)0.0028 (16)
C50.066 (2)0.0383 (19)0.048 (2)0.0054 (18)0.0225 (18)0.0037 (16)
C60.057 (2)0.0379 (19)0.048 (2)0.0036 (18)0.0205 (17)0.0006 (16)
C70.054 (2)0.046 (2)0.046 (2)0.0032 (18)0.0164 (18)0.0003 (17)
C80.052 (2)0.053 (2)0.046 (2)0.0070 (19)0.0130 (18)0.0035 (17)
C90.062 (2)0.056 (2)0.050 (2)0.007 (2)0.0244 (19)0.0059 (18)
C100.063 (3)0.060 (3)0.043 (2)0.007 (2)0.0069 (19)0.0028 (18)
C110.056 (2)0.097 (4)0.051 (3)0.016 (2)0.013 (2)0.000 (2)
C120.061 (3)0.090 (3)0.059 (3)0.013 (2)0.025 (2)0.006 (2)
C130.076 (3)0.076 (3)0.047 (2)0.004 (2)0.012 (2)0.000 (2)
C140.097 (4)0.096 (4)0.056 (3)0.016 (3)0.007 (3)0.006 (3)
C150.161 (6)0.121 (5)0.050 (3)0.034 (5)0.019 (3)0.011 (3)
C160.202 (9)0.244 (12)0.081 (5)0.077 (8)0.028 (5)0.041 (6)
C170.164 (9)0.41 (2)0.128 (8)0.079 (11)0.001 (7)0.052 (10)
C180.132 (6)0.218 (10)0.091 (5)0.004 (6)0.014 (4)0.003 (5)
Geometric parameters (Å, º) top
O1—C41.263 (4)O3—H19B0.82 (2)
O2—C101.375 (4)C2—H20.9300
N1—C21.367 (5)C3—H30.9300
N1—C61.360 (5)C5—H50.9300
N1—C71.439 (5)C6—H60.9300
O2—C131.433 (5)C8—H80.9300
C2—C31.334 (5)C9—H90.9300
C3—C41.430 (5)C11—H110.9300
C4—C51.423 (5)C12—H120.9300
C5—C61.359 (5)C13—H13A0.9700
C7—C121.377 (5)C13—H13B0.9700
C7—C81.376 (5)C14—H14A0.9700
C8—C91.387 (5)C14—H14B0.9700
C9—C101.380 (6)C15—H15A0.9700
C10—C111.380 (6)C15—H15B0.9700
C11—C121.361 (6)C16—H16A0.9700
C13—C141.513 (6)C16—H16B0.9700
C14—C151.477 (8)C17—H17A0.9700
C15—C161.563 (9)C17—H17B0.9700
C16—C171.504 (2)C18—H18A0.9600
C17—C181.508 (5)C18—H18B0.9600
O3—H19A0.85 (2)C18—H18C0.9600
C10—O2—C13117.7 (3)C10—C9—H9120.2
C6—N1—C2117.9 (3)C8—C9—H9120.2
C6—N1—C7120.5 (3)C12—C11—H11120.2
C2—N1—C7121.5 (3)C10—C11—H11120.2
C3—C2—N1122.3 (4)C11—C12—H12119.4
C2—C3—C4122.2 (4)C7—C12—H12119.4
O1—C4—C5123.0 (3)O2—C13—H13A110.2
O1—C4—C3123.0 (3)C14—C13—H13A110.2
C5—C4—C3113.9 (3)O2—C13—H13B110.2
C6—C5—C4121.5 (3)C14—C13—H13B110.2
C5—C6—N1122.2 (3)H13A—C13—H13B108.5
C8—C7—C12119.4 (4)C15—C14—H14A108.8
C8—C7—N1120.1 (3)C13—C14—H14A108.8
C12—C7—N1120.4 (3)C15—C14—H14B108.8
C7—C8—C9120.0 (4)C13—C14—H14B108.8
C10—C9—C8119.6 (4)H14A—C14—H14B107.7
O2—C10—C11116.1 (4)C14—C15—H15A110.5
O2—C10—C9123.7 (4)C16—C15—H15A110.5
C11—C10—C9120.2 (3)C14—C15—H15B110.5
C12—C11—C10119.6 (4)C16—C15—H15B110.5
C11—C12—C7121.2 (4)H15A—C15—H15B108.7
O2—C13—C14107.6 (4)C17—C16—H16A109.2
C15—C14—C13113.8 (5)C15—C16—H16A109.2
C14—C15—C16106.2 (6)C17—C16—H16B109.2
C17—C16—C15111.9 (7)C15—C16—H16B109.2
C16—C17—C18106.9 (6)H16A—C16—H16B107.9
H19A—O3—H19B103 (5)C16—C17—H17A110.3
C3—C2—H2118.9C18—C17—H17A110.3
N1—C2—H2118.9C16—C17—H17B110.3
C2—C3—H3118.9C18—C17—H17B110.3
C4—C3—H3118.9H17A—C17—H17B108.6
C6—C5—H5119.3C17—C18—H18A109.5
C4—C5—H5119.3C17—C18—H18B109.5
C5—C6—H6118.9H18A—C18—H18B109.5
N1—C6—H6118.9C17—C18—H18C109.5
C7—C8—H8120.0H18A—C18—H18C109.5
C9—C8—H8120.0H18B—C18—H18C109.5
C6—N1—C2—C30.2 (6)C7—C8—C9—C101.2 (6)
C7—N1—C2—C3178.3 (4)C13—O2—C10—C11155.8 (4)
N1—C2—C3—C40.1 (6)C13—O2—C10—C923.9 (6)
C2—C3—C4—O1179.0 (4)C8—C9—C10—O2179.2 (4)
C2—C3—C4—C50.4 (6)C8—C9—C10—C110.4 (6)
O1—C4—C5—C6179.0 (4)O2—C10—C11—C12179.4 (4)
C3—C4—C5—C60.4 (5)C9—C10—C11—C120.3 (7)
C4—C5—C6—N10.2 (6)C10—C11—C12—C71.5 (7)
C2—N1—C6—C50.1 (5)C8—C7—C12—C113.1 (7)
C7—N1—C6—C5178.3 (3)N1—C7—C12—C11176.5 (4)
C6—N1—C7—C846.7 (5)C10—O2—C13—C14163.9 (4)
C2—N1—C7—C8135.2 (4)O2—C13—C14—C15178.3 (5)
C6—N1—C7—C12132.8 (4)C13—C14—C15—C16178.0 (6)
C2—N1—C7—C1245.3 (5)C14—C15—C16—C17177.0 (8)
C12—C7—C8—C92.9 (6)C15—C16—C17—C18173.1 (7)
N1—C7—C8—C9176.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H19a···O10.84 (5)2.05 (5)2.873 (5)165 (5)
O3—H19b···O1i0.82 (5)2.03 (5)2.847 (4)177 (7)
Symmetry code: (i) x+2, y+1/2, z+5/2.
 

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