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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
CCDC reference: 271875
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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(1
H)-one monohydrate
top
Crystal data top
C17H21NO2·H2O | F(000) = 624 |
Mr = 289.36 | Dx = 1.169 Mg m−3 |
Monoclinic, P21/c | Melting point: 355.6 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71069 Å |
a = 17.815 (5) Å | Cell parameters from 25 reflections |
b = 8.022 (3) Å | θ = 10.0–11.0° |
c = 12.251 (3) Å | µ = 0.08 mm−1 |
β = 110.09 (2)° | T = 296 K |
V = 1644.3 (9) Å3 | Plate, colorless |
Z = 4 | 0.49 × 0.41 × 0.16 mm |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.017 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.4° |
Graphite monochromator | h = −21→19 |
ω scans | k = −9→0 |
3075 measured reflections | l = 0→14 |
2923 independent reflections | 3 standard reflections every 100 reflections |
1400 reflections with I > 2σ(I) | intensity decay: 0.6% |
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)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.280 | H 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 parameters | Δρmax = 0.52 e Å−3 |
6 restraints | Δρmin = −0.55 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.96070 (17) | 0.6274 (3) | 1.1453 (2) | 0.0570 (8) | |
O2 | 0.69011 (19) | 0.4240 (4) | 0.3275 (2) | 0.0789 (10) | |
O3 | 1.0719 (2) | 0.9003 (4) | 1.1981 (3) | 0.0743 (10) | |
N1 | 0.85177 (18) | 0.5276 (4) | 0.7993 (2) | 0.0473 (8) | |
C2 | 0.8411 (2) | 0.4264 (5) | 0.8826 (3) | 0.0546 (10) | |
C3 | 0.8757 (2) | 0.4570 (5) | 0.9959 (3) | 0.0542 (10) | |
C4 | 0.9266 (2) | 0.5978 (4) | 1.0384 (3) | 0.0471 (9) | |
C5 | 0.9360 (2) | 0.7007 (4) | 0.9493 (3) | 0.0497 (10) | |
C6 | 0.8994 (2) | 0.6637 (4) | 0.8350 (3) | 0.0470 (9) | |
C7 | 0.8122 (2) | 0.4951 (5) | 0.6775 (3) | 0.0488 (10) | |
C8 | 0.8540 (2) | 0.5059 (5) | 0.6019 (3) | 0.0510 (10) | |
C9 | 0.8148 (2) | 0.4832 (5) | 0.4837 (3) | 0.0546 (10) | |
C10 | 0.7342 (3) | 0.4467 (5) | 0.4430 (3) | 0.0583 (11) | |
C11 | 0.6930 (3) | 0.4320 (6) | 0.5195 (4) | 0.0694 (13) | |
C12 | 0.7324 (3) | 0.4543 (6) | 0.6353 (4) | 0.0687 (13) | |
C13 | 0.7189 (3) | 0.4995 (6) | 0.2434 (3) | 0.0686 (12) | |
C14 | 0.6508 (3) | 0.5004 (7) | 0.1281 (4) | 0.0879 (16) | |
C15 | 0.6724 (4) | 0.5708 (8) | 0.0315 (4) | 0.115 (2) | |
C16 | 0.5961 (5) | 0.5551 (13) | −0.0796 (6) | 0.181 (4) | |
C17 | 0.6111 (5) | 0.6146 (15) | −0.1868 (5) | 0.247 (8) | |
C18 | 0.5372 (4) | 0.5738 (12) | −0.2890 (5) | 0.160 (4) | |
H2 | 0.8086 | 0.3329 | 0.8594 | 0.066* | |
H3 | 0.8664 | 0.3843 | 1.0490 | 0.065* | |
H5 | 0.9679 | 0.7953 | 0.9698 | 0.060* | |
H6 | 0.9071 | 0.7339 | 0.7794 | 0.056* | |
H8 | 0.9085 | 0.5285 | 0.6300 | 0.061* | |
H9 | 0.8426 | 0.4925 | 0.4322 | 0.065* | |
H11 | 0.6387 | 0.4069 | 0.4922 | 0.083* | |
H12 | 0.7048 | 0.4418 | 0.6869 | 0.082* | |
H13A | 0.7637 | 0.4365 | 0.2370 | 0.082* | |
H13B | 0.7366 | 0.6125 | 0.2666 | 0.082* | |
H14A | 0.6321 | 0.3870 | 0.1086 | 0.106* | |
H14B | 0.6069 | 0.5646 | 0.1364 | 0.106* | |
H15A | 0.7165 | 0.5091 | 0.0217 | 0.138* | |
H15B | 0.6881 | 0.6866 | 0.0467 | 0.138* | |
H16A | 0.5792 | 0.4396 | −0.0899 | 0.217* | |
H16B | 0.5533 | 0.6202 | −0.0690 | 0.217* | |
H17A | 0.6573 | 0.5587 | −0.1943 | 0.296* | |
H17B | 0.6208 | 0.7338 | −0.1825 | 0.296* | |
H18A | 0.5476 | 0.5926 | −0.3599 | 0.240* | |
H18B | 0.4939 | 0.6437 | −0.2874 | 0.240* | |
H18C | 0.5232 | 0.4590 | −0.2849 | 0.240* | |
H19A | 1.042 (3) | 0.818 (5) | 1.196 (5) | 0.111* | |
H19B | 1.063 (4) | 0.963 (6) | 1.245 (4) | 0.111* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0796 (19) | 0.0502 (16) | 0.0403 (15) | −0.0005 (14) | 0.0193 (13) | −0.0059 (12) |
O2 | 0.083 (2) | 0.100 (2) | 0.0444 (17) | −0.0225 (19) | 0.0097 (15) | −0.0030 (15) |
O3 | 0.084 (2) | 0.080 (2) | 0.071 (2) | −0.0221 (17) | 0.0417 (18) | −0.0203 (17) |
N1 | 0.0549 (18) | 0.0453 (18) | 0.0400 (17) | −0.0019 (15) | 0.0142 (14) | −0.0005 (13) |
C2 | 0.070 (3) | 0.048 (2) | 0.046 (2) | −0.014 (2) | 0.0212 (19) | −0.0022 (17) |
C3 | 0.072 (3) | 0.048 (2) | 0.047 (2) | −0.006 (2) | 0.0258 (19) | 0.0032 (17) |
C4 | 0.060 (2) | 0.039 (2) | 0.044 (2) | 0.0062 (17) | 0.0203 (17) | −0.0028 (16) |
C5 | 0.066 (2) | 0.0383 (19) | 0.048 (2) | −0.0054 (18) | 0.0225 (18) | −0.0037 (16) |
C6 | 0.057 (2) | 0.0379 (19) | 0.048 (2) | −0.0036 (18) | 0.0205 (17) | 0.0006 (16) |
C7 | 0.054 (2) | 0.046 (2) | 0.046 (2) | −0.0032 (18) | 0.0164 (18) | 0.0003 (17) |
C8 | 0.052 (2) | 0.053 (2) | 0.046 (2) | −0.0070 (19) | 0.0130 (18) | −0.0035 (17) |
C9 | 0.062 (2) | 0.056 (2) | 0.050 (2) | −0.007 (2) | 0.0244 (19) | −0.0059 (18) |
C10 | 0.063 (3) | 0.060 (3) | 0.043 (2) | −0.007 (2) | 0.0069 (19) | −0.0028 (18) |
C11 | 0.056 (2) | 0.097 (4) | 0.051 (3) | −0.016 (2) | 0.013 (2) | 0.000 (2) |
C12 | 0.061 (3) | 0.090 (3) | 0.059 (3) | −0.013 (2) | 0.025 (2) | −0.006 (2) |
C13 | 0.076 (3) | 0.076 (3) | 0.047 (2) | 0.004 (2) | 0.012 (2) | 0.000 (2) |
C14 | 0.097 (4) | 0.096 (4) | 0.056 (3) | 0.016 (3) | 0.007 (3) | −0.006 (3) |
C15 | 0.161 (6) | 0.121 (5) | 0.050 (3) | 0.034 (5) | 0.019 (3) | 0.011 (3) |
C16 | 0.202 (9) | 0.244 (12) | 0.081 (5) | 0.077 (8) | 0.028 (5) | 0.041 (6) |
C17 | 0.164 (9) | 0.41 (2) | 0.128 (8) | 0.079 (11) | −0.001 (7) | −0.052 (10) |
C18 | 0.132 (6) | 0.218 (10) | 0.091 (5) | −0.004 (6) | −0.014 (4) | 0.003 (5) |
Geometric parameters (Å, º) top
O1—C4 | 1.263 (4) | O3—H19B | 0.82 (2) |
O2—C10 | 1.375 (4) | C2—H2 | 0.9300 |
N1—C2 | 1.367 (5) | C3—H3 | 0.9300 |
N1—C6 | 1.360 (5) | C5—H5 | 0.9300 |
N1—C7 | 1.439 (5) | C6—H6 | 0.9300 |
O2—C13 | 1.433 (5) | C8—H8 | 0.9300 |
C2—C3 | 1.334 (5) | C9—H9 | 0.9300 |
C3—C4 | 1.430 (5) | C11—H11 | 0.9300 |
C4—C5 | 1.423 (5) | C12—H12 | 0.9300 |
C5—C6 | 1.359 (5) | C13—H13A | 0.9700 |
C7—C12 | 1.377 (5) | C13—H13B | 0.9700 |
C7—C8 | 1.376 (5) | C14—H14A | 0.9700 |
C8—C9 | 1.387 (5) | C14—H14B | 0.9700 |
C9—C10 | 1.380 (6) | C15—H15A | 0.9700 |
C10—C11 | 1.380 (6) | C15—H15B | 0.9700 |
C11—C12 | 1.361 (6) | C16—H16A | 0.9700 |
C13—C14 | 1.513 (6) | C16—H16B | 0.9700 |
C14—C15 | 1.477 (8) | C17—H17A | 0.9700 |
C15—C16 | 1.563 (9) | C17—H17B | 0.9700 |
C16—C17 | 1.504 (2) | C18—H18A | 0.9600 |
C17—C18 | 1.508 (5) | C18—H18B | 0.9600 |
O3—H19A | 0.85 (2) | C18—H18C | 0.9600 |
| | | |
C10—O2—C13 | 117.7 (3) | C10—C9—H9 | 120.2 |
C6—N1—C2 | 117.9 (3) | C8—C9—H9 | 120.2 |
C6—N1—C7 | 120.5 (3) | C12—C11—H11 | 120.2 |
C2—N1—C7 | 121.5 (3) | C10—C11—H11 | 120.2 |
C3—C2—N1 | 122.3 (4) | C11—C12—H12 | 119.4 |
C2—C3—C4 | 122.2 (4) | C7—C12—H12 | 119.4 |
O1—C4—C5 | 123.0 (3) | O2—C13—H13A | 110.2 |
O1—C4—C3 | 123.0 (3) | C14—C13—H13A | 110.2 |
C5—C4—C3 | 113.9 (3) | O2—C13—H13B | 110.2 |
C6—C5—C4 | 121.5 (3) | C14—C13—H13B | 110.2 |
C5—C6—N1 | 122.2 (3) | H13A—C13—H13B | 108.5 |
C8—C7—C12 | 119.4 (4) | C15—C14—H14A | 108.8 |
C8—C7—N1 | 120.1 (3) | C13—C14—H14A | 108.8 |
C12—C7—N1 | 120.4 (3) | C15—C14—H14B | 108.8 |
C7—C8—C9 | 120.0 (4) | C13—C14—H14B | 108.8 |
C10—C9—C8 | 119.6 (4) | H14A—C14—H14B | 107.7 |
O2—C10—C11 | 116.1 (4) | C14—C15—H15A | 110.5 |
O2—C10—C9 | 123.7 (4) | C16—C15—H15A | 110.5 |
C11—C10—C9 | 120.2 (3) | C14—C15—H15B | 110.5 |
C12—C11—C10 | 119.6 (4) | C16—C15—H15B | 110.5 |
C11—C12—C7 | 121.2 (4) | H15A—C15—H15B | 108.7 |
O2—C13—C14 | 107.6 (4) | C17—C16—H16A | 109.2 |
C15—C14—C13 | 113.8 (5) | C15—C16—H16A | 109.2 |
C14—C15—C16 | 106.2 (6) | C17—C16—H16B | 109.2 |
C17—C16—C15 | 111.9 (7) | C15—C16—H16B | 109.2 |
C16—C17—C18 | 106.9 (6) | H16A—C16—H16B | 107.9 |
H19A—O3—H19B | 103 (5) | C16—C17—H17A | 110.3 |
C3—C2—H2 | 118.9 | C18—C17—H17A | 110.3 |
N1—C2—H2 | 118.9 | C16—C17—H17B | 110.3 |
C2—C3—H3 | 118.9 | C18—C17—H17B | 110.3 |
C4—C3—H3 | 118.9 | H17A—C17—H17B | 108.6 |
C6—C5—H5 | 119.3 | C17—C18—H18A | 109.5 |
C4—C5—H5 | 119.3 | C17—C18—H18B | 109.5 |
C5—C6—H6 | 118.9 | H18A—C18—H18B | 109.5 |
N1—C6—H6 | 118.9 | C17—C18—H18C | 109.5 |
C7—C8—H8 | 120.0 | H18A—C18—H18C | 109.5 |
C9—C8—H8 | 120.0 | H18B—C18—H18C | 109.5 |
| | | |
C6—N1—C2—C3 | −0.2 (6) | C7—C8—C9—C10 | −1.2 (6) |
C7—N1—C2—C3 | −178.3 (4) | C13—O2—C10—C11 | 155.8 (4) |
N1—C2—C3—C4 | −0.1 (6) | C13—O2—C10—C9 | −23.9 (6) |
C2—C3—C4—O1 | −179.0 (4) | C8—C9—C10—O2 | 179.2 (4) |
C2—C3—C4—C5 | 0.4 (6) | C8—C9—C10—C11 | −0.4 (6) |
O1—C4—C5—C6 | 179.0 (4) | O2—C10—C11—C12 | −179.4 (4) |
C3—C4—C5—C6 | −0.4 (5) | C9—C10—C11—C12 | 0.3 (7) |
C4—C5—C6—N1 | 0.2 (6) | C10—C11—C12—C7 | 1.5 (7) |
C2—N1—C6—C5 | 0.1 (5) | C8—C7—C12—C11 | −3.1 (7) |
C7—N1—C6—C5 | 178.3 (3) | N1—C7—C12—C11 | 176.5 (4) |
C6—N1—C7—C8 | 46.7 (5) | C10—O2—C13—C14 | −163.9 (4) |
C2—N1—C7—C8 | −135.2 (4) | O2—C13—C14—C15 | −178.3 (5) |
C6—N1—C7—C12 | −132.8 (4) | C13—C14—C15—C16 | 178.0 (6) |
C2—N1—C7—C12 | 45.3 (5) | C14—C15—C16—C17 | −177.0 (8) |
C12—C7—C8—C9 | 2.9 (6) | C15—C16—C17—C18 | 173.1 (7) |
N1—C7—C8—C9 | −176.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H19a···O1 | 0.84 (5) | 2.05 (5) | 2.873 (5) | 165 (5) |
O3—H19b···O1i | 0.82 (5) | 2.03 (5) | 2.847 (4) | 177 (7) |
Symmetry code: (i) −x+2, y+1/2, −z+5/2. |
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