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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2492.
Published online 2009 September 19. doi:  10.1107/S1600536809036897
PMCID: PMC2970321

N-Butyladamantane-1-carboxamide

Abstract

In the crystal of the title compound, C15H25NO, the mol­ecules are linked into chains propagating in [001] by inter­molecular N—H(...)O hydrogen bonds.

Related literature

For a related structure, see: SiMa (2009 [triangle]). For further synthetic details, see: Tadashi & Sasaki (1969 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2492-scheme1.jpg

Experimental

Crystal data

  • C15H25NO
  • M r = 235.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2492-efi1.jpg
  • a = 32.257 (7) Å
  • b = 9.4353 (19) Å
  • c = 9.5328 (19) Å
  • β = 101.69 (3)°
  • V = 2841.1 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 298 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: none
  • 14458 measured reflections
  • 3260 independent reflections
  • 1544 reflections with I > 2σ(I)
  • R int = 0.077

Refinement

  • R[F 2 > 2σ(F 2)] = 0.086
  • wR(F 2) = 0.246
  • S = 1.04
  • 3260 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809036897/hb5069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036897/hb5069Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

supplementary crystallographic information

Experimental

A solution of freshly prepared 1-adamantane carbonyl chloride (1 mmol, prepared by refluxing 1-adamantane carboxylic acid with 3M excess of SOCl2) in dry CH2Cl2 was added dropwise to a well stirred and ice-cooled solution of butanamine (1 mmol) and triethylamine (2 mmol) in the same solvent. After 24 h of stirring at room temperature, the solvents were removed in vacuo and the residue was recrystallized from methanol. Colourless prisms of (I) were obtained in 80% yield (Tadashi Sasaki et al., 1969).

Refinement

Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on the N or C atoms to which they are bonded, with Uiso(H) = 1.2Ueq(N,C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level, and all H atoms have been omitted for clarity.

Crystal data

C15H25NOF(000) = 1040
Mr = 235.36Dx = 1.100 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4730 reflections
a = 32.257 (7) Åθ = 3.0–27.8°
b = 9.4353 (19) ŵ = 0.07 mm1
c = 9.5328 (19) ÅT = 298 K
β = 101.69 (3)°Prism, colourless
V = 2841.1 (10) Å30.20 × 0.20 × 0.20 mm
Z = 8

Data collection

Rigaku SCXmini diffractometer1544 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.077
graphiteθmax = 27.5°, θmin = 3.0°
Detector resolution: 13.6612 pixels mm-1h = −41→41
ω scansk = −12→12
14458 measured reflectionsl = −12→12
3260 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.246H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0977P)2 + 2.030P] where P = (Fo2 + 2Fc2)/3
3260 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = −0.32 e Å3

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 (Å2)

xyzUiso*/Ueq
C10.30657 (10)−0.1173 (4)0.4805 (4)0.0671 (10)
H1A0.3025−0.10140.57740.080*
H1B0.3146−0.21570.47330.080*
C20.26562 (13)−0.0911 (5)0.3781 (5)0.0935 (13)
H2A0.2702−0.10380.28130.112*
H2B0.2453−0.16220.39410.112*
C30.24721 (15)0.0484 (6)0.3883 (7)0.143 (2)
H3A0.26430.11640.34880.172*
H3B0.25020.07050.48920.172*
C40.20314 (15)0.0729 (6)0.3200 (7)0.152 (2)
H4A0.19970.06090.21830.229*
H4B0.19520.16770.34030.229*
H4C0.18540.00650.35640.229*
C50.36027 (8)0.0693 (3)0.5470 (3)0.0431 (7)
C60.39355 (8)0.1604 (3)0.4964 (3)0.0411 (7)
C70.41628 (10)0.2560 (4)0.6189 (3)0.0615 (9)
H7A0.39570.31540.65240.074*
H7B0.43030.19790.69840.074*
C80.44885 (11)0.3491 (4)0.5667 (4)0.0715 (10)
H80.46300.40950.64560.086*
C90.48163 (10)0.2564 (4)0.5166 (4)0.0795 (11)
H9A0.50250.31550.48440.095*
H9B0.49610.19810.59520.095*
C100.45958 (10)0.1630 (4)0.3948 (4)0.0614 (9)
H100.48060.10310.36240.074*
C110.42699 (9)0.0688 (3)0.4458 (3)0.0525 (8)
H11A0.44110.00910.52380.063*
H11B0.41340.00780.36800.063*
C120.37184 (9)0.2551 (3)0.3720 (3)0.0513 (8)
H12A0.35760.19650.29320.062*
H12B0.35070.31400.40300.062*
C130.40482 (11)0.3492 (3)0.3218 (3)0.0619 (9)
H130.39070.40890.24220.074*
C140.42639 (12)0.4422 (4)0.4441 (4)0.0773 (11)
H14A0.40560.50120.47650.093*
H14B0.44670.50360.41210.093*
C150.43746 (11)0.2543 (4)0.2710 (3)0.0674 (10)
H15A0.42340.19450.19290.081*
H15B0.45810.31250.23640.081*
N10.34081 (7)−0.0273 (3)0.4547 (2)0.0582 (7)
H1C0.3501−0.02780.36220.070*
O10.35154 (7)0.0859 (2)0.6660 (2)0.0619 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.062 (2)0.075 (2)0.065 (2)−0.0255 (18)0.0153 (18)0.0110 (18)
C20.074 (3)0.087 (3)0.123 (4)−0.018 (2)0.028 (3)0.022 (3)
C30.086 (3)0.105 (4)0.244 (7)0.001 (3)0.044 (4)0.024 (4)
C40.085 (4)0.126 (5)0.245 (8)0.003 (3)0.030 (4)0.008 (5)
C50.0435 (16)0.0514 (18)0.0365 (14)0.0034 (13)0.0128 (13)0.0079 (13)
C60.0425 (15)0.0466 (16)0.0357 (14)−0.0005 (12)0.0111 (12)−0.0016 (12)
C70.069 (2)0.072 (2)0.0451 (17)−0.0157 (18)0.0151 (15)−0.0170 (15)
C80.076 (2)0.078 (2)0.061 (2)−0.032 (2)0.0136 (19)−0.0210 (19)
C90.055 (2)0.098 (3)0.085 (3)−0.029 (2)0.0109 (19)−0.003 (2)
C100.0479 (17)0.071 (2)0.072 (2)−0.0038 (16)0.0278 (17)−0.0084 (18)
C110.0473 (16)0.0553 (19)0.0565 (18)0.0001 (14)0.0142 (14)0.0015 (14)
C120.0528 (17)0.0508 (18)0.0497 (17)−0.0002 (14)0.0090 (14)0.0037 (14)
C130.070 (2)0.056 (2)0.060 (2)−0.0064 (16)0.0150 (17)0.0139 (16)
C140.093 (3)0.050 (2)0.094 (3)−0.0227 (19)0.032 (2)−0.0086 (19)
C150.070 (2)0.081 (2)0.059 (2)−0.0260 (19)0.0307 (17)−0.0057 (18)
N10.0609 (16)0.0749 (18)0.0441 (13)−0.0258 (14)0.0234 (12)−0.0055 (13)
O10.0715 (15)0.0796 (16)0.0407 (11)−0.0063 (12)0.0263 (11)0.0002 (11)

Geometric parameters (Å, °)

C1—N11.453 (4)C8—C91.522 (5)
C1—C21.496 (5)C8—C141.523 (5)
C1—H1A0.9700C8—H80.9800
C1—H1B0.9700C9—C101.516 (5)
C2—C31.456 (6)C9—H9A0.9700
C2—H2A0.9700C9—H9B0.9700
C2—H2B0.9700C10—C151.517 (5)
C3—C41.457 (6)C10—C111.529 (4)
C3—H3A0.9700C10—H100.9800
C3—H3B0.9700C11—H11A0.9700
C4—H4A0.9600C11—H11B0.9700
C4—H4B0.9600C12—C131.535 (4)
C4—H4C0.9600C12—H12A0.9700
C5—O11.232 (3)C12—H12B0.9700
C5—N11.333 (3)C13—C141.512 (4)
C5—C61.527 (4)C13—C151.533 (5)
C6—C111.535 (4)C13—H130.9800
C6—C121.536 (4)C14—H14A0.9700
C6—C71.539 (4)C14—H14B0.9700
C7—C81.528 (4)C15—H15A0.9700
C7—H7A0.9700C15—H15B0.9700
C7—H7B0.9700N1—H1C0.9861
N1—C1—C2113.2 (3)C10—C9—C8109.1 (3)
N1—C1—H1A108.9C10—C9—H9A109.9
C2—C1—H1A108.9C8—C9—H9A109.9
N1—C1—H1B108.9C10—C9—H9B109.9
C2—C1—H1B108.9C8—C9—H9B109.9
H1A—C1—H1B107.8H9A—C9—H9B108.3
C3—C2—C1115.1 (4)C9—C10—C15109.8 (3)
C3—C2—H2A108.5C9—C10—C11109.9 (3)
C1—C2—H2A108.5C15—C10—C11109.4 (3)
C3—C2—H2B108.5C9—C10—H10109.2
C1—C2—H2B108.5C15—C10—H10109.2
H2A—C2—H2B107.5C11—C10—H10109.2
C2—C3—C4119.2 (5)C10—C11—C6110.2 (2)
C2—C3—H3A107.5C10—C11—H11A109.6
C4—C3—H3A107.5C6—C11—H11A109.6
C2—C3—H3B107.5C10—C11—H11B109.6
C4—C3—H3B107.5C6—C11—H11B109.6
H3A—C3—H3B107.0H11A—C11—H11B108.1
C3—C4—H4A109.5C13—C12—C6110.0 (2)
C3—C4—H4B109.5C13—C12—H12A109.7
H4A—C4—H4B109.5C6—C12—H12A109.7
C3—C4—H4C109.5C13—C12—H12B109.7
H4A—C4—H4C109.5C6—C12—H12B109.7
H4B—C4—H4C109.5H12A—C12—H12B108.2
O1—C5—N1122.0 (2)C14—C13—C15110.1 (3)
O1—C5—C6121.7 (3)C14—C13—C12109.6 (3)
N1—C5—C6116.3 (2)C15—C13—C12108.9 (3)
C5—C6—C11111.5 (2)C14—C13—H13109.4
C5—C6—C12109.4 (2)C15—C13—H13109.4
C11—C6—C12108.9 (2)C12—C13—H13109.4
C5—C6—C7110.3 (2)C13—C14—C8109.3 (3)
C11—C6—C7108.2 (2)C13—C14—H14A109.8
C12—C6—C7108.5 (2)C8—C14—H14A109.8
C8—C7—C6110.1 (2)C13—C14—H14B109.8
C8—C7—H7A109.6C8—C14—H14B109.8
C6—C7—H7A109.6H14A—C14—H14B108.3
C8—C7—H7B109.6C10—C15—C13109.3 (3)
C6—C7—H7B109.6C10—C15—H15A109.8
H7A—C7—H7B108.2C13—C15—H15A109.8
C9—C8—C14110.1 (3)C10—C15—H15B109.8
C9—C8—C7109.8 (3)C13—C15—H15B109.8
C14—C8—C7109.3 (3)H15A—C15—H15B108.3
C9—C8—H8109.2C5—N1—C1124.1 (2)
C14—C8—H8109.2C5—N1—H1C113.9
C7—C8—H8109.2C1—N1—H1C121.8
N1—C1—C2—C3−65.2 (5)C5—C6—C11—C10179.5 (2)
C1—C2—C3—C4−165.0 (5)C12—C6—C11—C1058.8 (3)
O1—C5—C6—C11126.9 (3)C7—C6—C11—C10−59.0 (3)
N1—C5—C6—C11−54.1 (3)C5—C6—C12—C13179.0 (2)
O1—C5—C6—C12−112.6 (3)C11—C6—C12—C13−58.9 (3)
N1—C5—C6—C1266.4 (3)C7—C6—C12—C1358.6 (3)
O1—C5—C6—C76.6 (4)C6—C12—C13—C14−60.3 (3)
N1—C5—C6—C7−174.4 (2)C6—C12—C13—C1560.2 (3)
C5—C6—C7—C8−178.8 (3)C15—C13—C14—C8−58.9 (4)
C11—C6—C7—C859.0 (3)C12—C13—C14—C861.0 (4)
C12—C6—C7—C8−59.0 (3)C9—C8—C14—C1359.6 (4)
C6—C7—C8—C9−60.3 (4)C7—C8—C14—C13−61.1 (4)
C6—C7—C8—C1460.5 (4)C9—C10—C15—C13−59.7 (3)
C14—C8—C9—C10−60.2 (4)C11—C10—C15—C1361.0 (3)
C7—C8—C9—C1060.1 (4)C14—C13—C15—C1059.2 (3)
C8—C9—C10—C1560.3 (3)C12—C13—C15—C10−61.0 (3)
C8—C9—C10—C11−60.1 (4)O1—C5—N1—C12.9 (5)
C9—C10—C11—C660.4 (3)C6—C5—N1—C1−176.1 (3)
C15—C10—C11—C6−60.2 (3)C2—C1—N1—C5115.9 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.991.962.896 (3)158

Symmetry codes: (i) x, −y, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5069).

References

  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • SiMa, W. (2009). Acta Cryst E65, o2452. [PMC free article] [PubMed]
  • Tadashi, X. & Sasaki, Y. (1969). Bull. Chem. Soc. Jpn, 42, 1617–1621.

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