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The crystal structure of the title compound, C14H17NO2, is stabilized by three inter­molecular C—H...O hydrogen bonds and one π–π inter­action. C—H...O hydrogen bonds generate an edge-fused [R33(13)R42(14)R33(13)] ring motif.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602277X/dn2050sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602277X/dn2050Isup2.hkl
Contains datablock I

CCDC reference: 613667

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.059
  • wR factor = 0.141
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.101 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(4-methylpiperidin-1-yl)isobenzofuran-1(3H)-one top
Crystal data top
C14H17NO2F(000) = 496
Mr = 231.29Dx = 1.204 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 17106 reflections
a = 12.7916 (11) Åθ = 2.5–28.2°
b = 8.0661 (11) ŵ = 0.08 mm1
c = 12.3650 (11) ÅT = 296 K
β = 90.266 (7)°Prism, colorless
V = 1275.8 (2) Å30.62 × 0.49 × 0.33 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
2504 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1663 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.101
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.0°
ω scansh = 1515
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 99
Tmin = 0.954, Tmax = 0.976l = 1515
17106 measured reflections
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)] = 0.059H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0499P)2 + 0.1775P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
2504 reflectionsΔρmax = 0.16 e Å3
155 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0097 (19)
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
C10.11241 (17)0.7503 (3)0.41310 (17)0.0608 (6)
C20.11769 (15)0.5698 (3)0.42509 (15)0.0538 (5)
C30.08413 (17)0.4457 (3)0.35555 (19)0.0708 (7)
H30.05420.47080.28890.085*
C40.09657 (19)0.2849 (4)0.3885 (3)0.0831 (8)
H40.07460.19930.34340.100*
C50.14129 (19)0.2477 (3)0.4876 (3)0.0820 (8)
H50.14840.13730.50820.098*
C60.17573 (18)0.3713 (3)0.5568 (2)0.0710 (7)
H60.20610.34570.62320.085*
C70.16353 (15)0.5340 (3)0.52386 (15)0.0529 (5)
C80.18915 (16)0.6917 (3)0.58149 (15)0.0552 (5)
H80.14730.69780.64750.066*
C90.31507 (18)0.8530 (3)0.68295 (17)0.0666 (6)
H9A0.26630.84800.74270.080*
H9B0.30380.95660.64490.080*
C100.42549 (18)0.8469 (3)0.72585 (17)0.0683 (6)
H10A0.43500.74610.76760.082*
H10B0.43700.94030.77380.082*
C110.50524 (17)0.8516 (3)0.63567 (17)0.0612 (6)
H110.49710.95770.59790.073*
C120.48028 (17)0.7142 (3)0.55506 (17)0.0618 (6)
H12A0.52570.72540.49290.074*
H12B0.49480.60780.58840.074*
C130.36714 (16)0.7175 (3)0.51716 (15)0.0568 (5)
H13A0.35470.81710.47510.068*
H13B0.35370.62260.47100.068*
C140.6173 (2)0.8424 (4)0.6775 (2)0.0903 (8)
H14A0.66470.84610.61760.135*
H14B0.62710.74080.71660.135*
H14C0.63070.93460.72460.135*
N10.29604 (13)0.7137 (2)0.60936 (12)0.0526 (4)
O10.08066 (14)0.8329 (2)0.33850 (13)0.0855 (6)
O20.15141 (11)0.82115 (18)0.50444 (11)0.0625 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0532 (13)0.0703 (15)0.0589 (12)0.0024 (11)0.0028 (10)0.0039 (11)
C20.0456 (11)0.0605 (14)0.0554 (12)0.0019 (9)0.0020 (9)0.0042 (10)
C30.0545 (13)0.086 (2)0.0720 (14)0.0055 (12)0.0043 (11)0.0202 (13)
C40.0562 (15)0.0771 (19)0.116 (2)0.0100 (12)0.0001 (15)0.0364 (17)
C50.0623 (16)0.0517 (14)0.132 (2)0.0029 (12)0.0053 (16)0.0030 (15)
C60.0614 (15)0.0657 (16)0.0858 (16)0.0021 (11)0.0047 (12)0.0106 (13)
C70.0465 (11)0.0564 (13)0.0558 (11)0.0029 (9)0.0003 (9)0.0001 (10)
C80.0562 (12)0.0591 (14)0.0503 (10)0.0011 (10)0.0003 (9)0.0012 (9)
C90.0670 (14)0.0757 (16)0.0573 (12)0.0059 (12)0.0049 (11)0.0206 (11)
C100.0754 (16)0.0770 (16)0.0524 (11)0.0114 (12)0.0055 (11)0.0126 (11)
C110.0600 (13)0.0620 (14)0.0616 (12)0.0041 (10)0.0053 (10)0.0001 (10)
C120.0570 (13)0.0691 (15)0.0592 (12)0.0018 (10)0.0004 (10)0.0054 (10)
C130.0605 (13)0.0641 (14)0.0459 (10)0.0018 (10)0.0019 (9)0.0034 (9)
C140.0666 (16)0.097 (2)0.107 (2)0.0039 (14)0.0179 (14)0.0152 (16)
N10.0532 (10)0.0624 (11)0.0424 (8)0.0052 (8)0.0011 (7)0.0065 (7)
O10.0872 (13)0.0939 (14)0.0753 (11)0.0105 (10)0.0146 (9)0.0234 (9)
O20.0666 (10)0.0532 (9)0.0675 (9)0.0047 (7)0.0083 (7)0.0013 (7)
Geometric parameters (Å, º) top
C1—O11.207 (2)C9—C101.507 (3)
C1—O21.359 (3)C9—H9A0.9700
C1—C21.465 (3)C9—H9B0.9700
C2—C71.383 (3)C10—C111.515 (3)
C2—C31.387 (3)C10—H10A0.9700
C3—C41.368 (4)C10—H10B0.9700
C3—H30.9300C11—C141.523 (3)
C4—C51.383 (4)C11—C121.524 (3)
C4—H40.9300C11—H110.9800
C5—C61.384 (4)C12—C131.519 (3)
C5—H50.9300C12—H12A0.9700
C6—C71.383 (3)C12—H12B0.9700
C6—H60.9300C13—N11.462 (2)
C7—C81.494 (3)C13—H13A0.9700
C8—N11.420 (2)C13—H13B0.9700
C8—O21.492 (2)C14—H14A0.9600
C8—H80.9800C14—H14B0.9600
C9—N11.465 (3)C14—H14C0.9600
O1—C1—O2121.6 (2)C9—C10—H10A109.2
O1—C1—C2129.9 (2)C11—C10—H10A109.2
O2—C1—C2108.51 (18)C9—C10—H10B109.2
C7—C2—C3121.7 (2)C11—C10—H10B109.2
C7—C2—C1108.43 (18)H10A—C10—H10B107.9
C3—C2—C1129.9 (2)C10—C11—C14112.62 (19)
C4—C3—C2117.7 (2)C10—C11—C12108.86 (18)
C4—C3—H3121.2C14—C11—C12112.4 (2)
C2—C3—H3121.2C10—C11—H11107.6
C3—C4—C5121.1 (2)C14—C11—H11107.6
C3—C4—H4119.5C12—C11—H11107.6
C5—C4—H4119.5C13—C12—C11112.68 (18)
C4—C5—C6121.4 (3)C13—C12—H12A109.1
C4—C5—H5119.3C11—C12—H12A109.1
C6—C5—H5119.3C13—C12—H12B109.1
C7—C6—C5117.8 (2)C11—C12—H12B109.1
C7—C6—H6121.1H12A—C12—H12B107.8
C5—C6—H6121.1N1—C13—C12110.75 (16)
C2—C7—C6120.3 (2)N1—C13—H13A109.5
C2—C7—C8109.56 (18)C12—C13—H13A109.5
C6—C7—C8130.07 (19)N1—C13—H13B109.5
N1—C8—O2112.08 (16)C12—C13—H13B109.5
N1—C8—C7115.55 (17)H13A—C13—H13B108.1
O2—C8—C7102.80 (15)C11—C14—H14A109.5
N1—C8—H8108.7C11—C14—H14B109.5
O2—C8—H8108.7H14A—C14—H14B109.5
C7—C8—H8108.7C11—C14—H14C109.5
N1—C9—C10110.25 (19)H14A—C14—H14C109.5
N1—C9—H9A109.6H14B—C14—H14C109.5
C10—C9—H9A109.6C8—N1—C13114.54 (15)
N1—C9—H9B109.6C8—N1—C9113.81 (17)
C10—C9—H9B109.6C13—N1—C9111.48 (16)
H9A—C9—H9B108.1C1—O2—C8110.66 (16)
C9—C10—C11111.91 (17)
O1—C1—C2—C7178.0 (2)N1—C9—C10—C1158.4 (3)
O2—C1—C2—C71.8 (2)C9—C10—C11—C14179.0 (2)
O1—C1—C2—C32.6 (4)C9—C10—C11—C1253.7 (3)
O2—C1—C2—C3177.5 (2)C10—C11—C12—C1351.7 (2)
C7—C2—C3—C40.8 (3)C14—C11—C12—C13177.2 (2)
C1—C2—C3—C4178.4 (2)C11—C12—C13—N154.4 (2)
C2—C3—C4—C50.1 (3)O2—C8—N1—C1356.3 (2)
C3—C4—C5—C60.5 (4)C7—C8—N1—C1361.0 (2)
C4—C5—C6—C70.3 (4)O2—C8—N1—C973.6 (2)
C3—C2—C7—C61.0 (3)C7—C8—N1—C9169.08 (17)
C1—C2—C7—C6178.4 (2)C12—C13—N1—C8171.13 (18)
C3—C2—C7—C8178.75 (19)C12—C13—N1—C957.8 (2)
C1—C2—C7—C80.7 (2)C10—C9—N1—C8168.63 (17)
C5—C6—C7—C20.4 (3)C10—C9—N1—C1360.0 (2)
C5—C6—C7—C8177.6 (2)O1—C1—O2—C8177.6 (2)
C2—C7—C8—N1121.79 (18)C2—C1—O2—C82.3 (2)
C6—C7—C8—N160.7 (3)N1—C8—O2—C1122.92 (18)
C2—C7—C8—O20.6 (2)C7—C8—O2—C11.8 (2)
C6—C7—C8—O2176.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.583.314 (3)136
C5—H5···O2ii0.932.553.449 (3)162
C8—H8···O1iii0.982.533.479 (3)164
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y1, z; (iii) x, y+3/2, z+1/2.
 

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