1-(1-Adamantyl­oxy)pyridin-2(1H)-one

The bond angle at the bridging O atom between the two subunits of the title compound, C₁₅H₁₈NO₂, is 114.1 (5)°, which exceeds the values reported for structurally related 1-(alk­oxy)pyridin-2(1H)-ones. The pyridone ring and the alk­oxy substituent are located on a mirror plane so that the carbonyl O atom is disordered over two positions with occupancies of 50%.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.011 Å
• Disorder in main residue
• R factor = 0.082
• wR factor = 0.303
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level A
RINTA01_ALERT_3_A  The value of Rint is greater than 0.20
            Rint given   0.233

Author Response: The structure was solved in P21/c, which clearly showed that O2 and O2a exhibit an occupancy of 50 %. In view of the existing mirror plane that was located in the molecule, the structure was transformed and refined in Pnma. The CIF-check routine then suggested to split C2, C3, and C4. This has been done, however leading to disturbing C-C bond lengths for the heterocyclic subunit ranging between 1.1 \%A to 1.9 \%A. The origin of this problem seems in our eyes to be associated with the quality of the selcted crystal. The compound was prepared in a project that ended several years ago and unfortunately is no longer available in our laboratories. In order to present the first solid state geometry of a tertiary cylic hydroxamic acid O-ester, we therefore chose the present data. The structural discussion has been supplementented with valuable in formation from reference compounds and also with spectroscopic data obtained for the title compound in solution. In view of these cumulative facts we would be pleased to present the structure in Acta E.

PLAT020_ALERT_3_A The value of Rint is greater than 0.10 .........       0.23

Author Response: See answer to question vrf_RINTA01_har33.

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         31 Perc.
PLAT213_ALERT_2_B Atom C4      has ADP max/min Ratio .............       4.20 prolat
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.83 Ratio
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT410_ALERT_2_B Short Intra H...H Contact  H6A    ..  H9      ..       1.87 Ang.
PLAT731_ALERT_1_B Bond    Calc     0.97(7), Rep   0.972(10) ......       7.00 su-Rat
              C10  -H10B    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   0.303
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT084_ALERT_2_C High R2 Value ..................................       0.30
PLAT213_ALERT_2_C Atom C3      has ADP max/min Ratio .............       3.30 prolat
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.84
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O2
PLAT320_ALERT_2_C Check Hybridisation of  C9     in Main Residue .          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C2      ..       2.95 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.98(3), Rep   0.986(10) ......       3.00 su-Rat
              C9   -H9      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.97(4), Rep   0.971(10) ......       4.00 su-Rat
              C10  -H10A    1.555   1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.33 Ratio

   2 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
  13 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
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Diffractometer Control Software (Enraf–Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; 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 PLATON2002 (Spek, 2003); software used to prepare material for publication: SHELXL97.

1-(Adamant-1-yloxy)pyridin-2(1H)-one

Crystal data

C15H18NO2	F(000) = 524
Mr = 244.30	Dx = 1.296 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 25 reflections
a = 16.982 (3) Å	θ = 3.0–11.1°
b = 6.559 (3) Å	µ = 0.09 mm^−1
c = 11.237 (2) Å	T = 299 K
V = 1251.6 (7) Å^3	Needle, colourless
Z = 4	0.70 × 0.10 × 0.03 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.233
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 4.3°
Graphite monochromator	h = 0→20
ω/2θ scans	k = −7→5
2132 measured reflections	l = 0→13
1256 independent reflections	3 standard reflections every 120 min
385 reflections with I > 2σ(I)	intensity decay: 1.2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.303	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1203P)^2 + 0.3693P] where P = (Fo^2 + 2Fc^2)/3
1256 reflections	(Δ/σ)max = 0.017
106 parameters	Δρmax = 0.20 e Å^−3
3 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C2	0.2127 (4)	0.563 (2)	0.4245 (7)	0.118 (4)
C3	0.2514 (4)	0.566 (2)	0.5379 (7)	0.155 (6)
H3	0.2641	0.4448	0.5764	0.186*
C4	0.2696 (8)	0.7500	0.5888 (12)	0.205 (16)
H4	0.2956	0.7500	0.6617	0.247*
C5	0.0736 (4)	0.7500	0.2668 (6)	0.054 (3)
C6	0.0397 (4)	0.9317 (13)	0.3229 (6)	0.079 (2)
H6A	0.0625	1.0529	0.2874	0.094*
H6B	0.0526	0.9321	0.4070	0.094*
C7	−0.0502 (4)	0.9372 (14)	0.3077 (6)	0.086 (2)
H7	−0.0718	1.0593	0.3459	0.104*
C8	−0.0830 (6)	0.7500	0.3652 (9)	0.090 (4)
H8A	−0.1399	0.7500	0.3579	0.108*
H8B	−0.0699	0.7500	0.4492	0.108*
C9	0.0567 (6)	0.7500	0.1322 (8)	0.080 (3)
H9	0.065 (4)	0.896 (3)	0.148 (6)	0.096*
C10	−0.0674 (5)	0.558 (2)	0.1742 (7)	0.115 (3)
H10A	−0.1227 (16)	0.594 (13)	0.168 (7)	0.138*
H10B	−0.043 (5)	0.446 (9)	0.131 (7)	0.138*
C11	−0.0351 (6)	0.7500	0.1170 (9)	0.088 (4)
H11	−0.0482	0.7500	0.0321	0.106*
N1	0.1932 (4)	0.7500	0.3800 (7)	0.082 (3)
O1	0.1600 (3)	0.7500	0.2671 (4)	0.076 (2)
O2	0.1959 (5)	0.3690 (17)	0.3545 (9)	0.085 (3)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.037 (3)	0.239 (13)	0.077 (6)	0.000 (6)	0.006 (3)	0.058 (8)
C3	0.048 (5)	0.353 (18)	0.065 (6)	−0.008 (8)	−0.015 (4)	0.075 (9)
C4	0.036 (7)	0.54 (5)	0.044 (8)	0.000	−0.009 (5)	0.000
C5	0.033 (4)	0.094 (8)	0.036 (4)	0.000	0.000 (3)	0.000
C6	0.058 (4)	0.108 (6)	0.070 (4)	0.007 (4)	0.001 (3)	−0.001 (5)
C7	0.070 (4)	0.116 (7)	0.073 (4)	0.029 (5)	0.004 (4)	0.006 (5)
C8	0.053 (6)	0.145 (12)	0.072 (7)	0.000	0.006 (5)	0.000
C9	0.073 (6)	0.126 (10)	0.040 (5)	0.000	−0.010 (5)	0.000
C10	0.070 (5)	0.189 (11)	0.085 (6)	−0.027 (7)	−0.016 (4)	−0.029 (6)
C11	0.060 (6)	0.157 (14)	0.047 (5)	0.000	−0.009 (5)	0.000
N1	0.040 (4)	0.171 (11)	0.036 (4)	0.000	0.004 (4)	0.000
O1	0.035 (3)	0.163 (7)	0.031 (3)	0.000	0.000 (2)	0.000
O2	0.067 (6)	0.103 (8)	0.085 (6)	0.009 (5)	−0.012 (5)	0.019 (6)

Geometric parameters (Å, º)

C2—N1	1.368 (12)	C7—H7	0.9800
C2—C3	1.433 (11)	C8—C7^i	1.495 (8)
C2—O2	1.521 (13)	C8—H8A	0.9700
C3—C4	1.371 (13)	C8—H8B	0.9700
C3—H3	0.9300	C9—C11	1.568 (14)
C4—C3^i	1.371 (13)	C9—H9	0.986 (10)
C4—H4	0.9300	C10—C11	1.515 (12)
C5—C6	1.466 (8)	C10—C7^i	1.529 (10)
C5—C6^i	1.466 (8)	C10—H10A	0.971 (10)
C5—O1	1.468 (9)	C10—H10B	0.972 (10)
C5—C9	1.540 (11)	C11—C10^i	1.515 (12)
C6—C7	1.537 (9)	C11—H11	0.9800
C6—H6A	0.9700	N1—C2^i	1.368 (12)
C6—H6B	0.9700	N1—O1	1.387 (9)
C7—C8	1.495 (8)	O2—O2^ii	1.56 (2)
C7—C10^i	1.529 (10)
N1—C2—C3	115.0 (13)	C7—C8—C7^i	110.4 (9)
N1—C2—O2	121.0 (6)	C7—C8—H8A	109.6
C3—C2—O2	124.0 (12)	C7^i—C8—H8A	109.6
C4—C3—C2	119.2 (13)	C7—C8—H8B	109.6
C4—C3—H3	120.4	C7^i—C8—H8B	109.6
C2—C3—H3	120.4	H8A—C8—H8B	108.1
C3—C4—C3^i	123.4 (12)	C5—C9—C11	107.0 (8)
C3—C4—H4	118.3	C5—C9—H9	78 (4)
C3^i—C4—H4	118.3	C11—C9—H9	99 (5)
C6—C5—C6^i	108.8 (8)	C11—C10—C7^i	109.3 (9)
C6—C5—O1	113.0 (4)	C11—C10—H10A	97 (6)
C6^i—C5—O1	113.0 (4)	C7^i—C10—H10A	105 (5)
C6—C5—C9	110.4 (5)	C11—C10—H10B	105 (6)
C6^i—C5—C9	110.4 (5)	C7^i—C10—H10B	115 (6)
O1—C5—C9	100.9 (6)	H10A—C10—H10B	123 (8)
C5—C6—C7	111.2 (7)	C10—C11—C10^i	112.2 (10)
C5—C6—H6A	109.4	C10—C11—C9	108.3 (6)
C7—C6—H6A	109.4	C10^i—C11—C9	108.3 (6)
C5—C6—H6B	109.4	C10—C11—H11	109.3
C7—C6—H6B	109.4	C10^i—C11—H11	109.3
H6A—C6—H6B	108.0	C9—C11—H11	109.3
C8—C7—C10^i	111.6 (9)	C2^i—N1—C2	127.9 (12)
C8—C7—C6	107.6 (7)	C2^i—N1—O1	115.7 (6)
C10^i—C7—C6	107.4 (6)	C2—N1—O1	115.7 (6)
C8—C7—H7	110.0	N1—O1—C5	114.1 (5)
C10^i—C7—H7	110.0	C2—O2—O2^ii	146.6 (5)
C6—C7—H7	110.0

Symmetry codes: (i) x, −y+3/2, z; (ii) x, −y+1/2, z.