organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N-Butyladamantane-1-carboxamide

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: nysima@126.com

(Received 25 August 2009; accepted 12 September 2009; online 19 September 2009)

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[SiMa, W. (2009). Acta Cryst. E65, o2452.]). For further synthetic details, see: Tadashi & Sasaki (1969[Tadashi, X. & Sasaki, Y. (1969). Bull. Chem. Soc. Jpn, 42, 1617-1621.]).

[Scheme 1]

Experimental

Crystal data
  • C15H25NO

  • Mr = 235.36

  • Monoclinic, C 2/c

  • 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)

  • Rint = 0.077

Refinement
  • R[F2 > 2σ(F2)] = 0.086

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1C⋯O1i 0.99 1.96 2.896 (3) 158
Symmetry code: (i) [x, -y, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] 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.
N-Butyladamantane-1-carboxamide top
Crystal data top
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 top
Rigaku SCXmini
diffractometer
1544 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.077
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
Detector resolution: 13.6612 pixels mm-1h = 4141
ω scansk = 1212
14458 measured reflectionsl = 1212
3260 independent reflections
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)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.246H-atom parameters constrained
S = 1.04 w = 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
Crystal data top
C15H25NOV = 2841.1 (10) Å3
Mr = 235.36Z = 8
Monoclinic, C2/cMo Kα radiation
a = 32.257 (7) ŵ = 0.07 mm1
b = 9.4353 (19) ÅT = 298 K
c = 9.5328 (19) Å0.20 × 0.20 × 0.20 mm
β = 101.69 (3)°
Data collection top
Rigaku SCXmini
diffractometer
1544 reflections with I > 2σ(I)
14458 measured reflectionsRint = 0.077
3260 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0860 restraints
wR(F2) = 0.246H-atom parameters constrained
S = 1.04Δρmax = 0.36 e Å3
3260 reflectionsΔρmin = 0.32 e Å3
155 parameters
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
C10.30657 (10)0.1173 (4)0.4805 (4)0.0671 (10)
H1A0.30250.10140.57740.080*
H1B0.31460.21570.47330.080*
C20.26562 (13)0.0911 (5)0.3781 (5)0.0935 (13)
H2A0.27020.10380.28130.112*
H2B0.24530.16220.39410.112*
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)
H1C0.35010.02780.36220.070*
O10.35154 (7)0.0859 (2)0.6660 (2)0.0619 (7)
Atomic displacement parameters (Å2) top
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, º) top
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—C365.2 (5)C5—C6—C11—C10179.5 (2)
C1—C2—C3—C4165.0 (5)C12—C6—C11—C1058.8 (3)
O1—C5—C6—C11126.9 (3)C7—C6—C11—C1059.0 (3)
N1—C5—C6—C1154.1 (3)C5—C6—C12—C13179.0 (2)
O1—C5—C6—C12112.6 (3)C11—C6—C12—C1358.9 (3)
N1—C5—C6—C1266.4 (3)C7—C6—C12—C1358.6 (3)
O1—C5—C6—C76.6 (4)C6—C12—C13—C1460.3 (3)
N1—C5—C6—C7174.4 (2)C6—C12—C13—C1560.2 (3)
C5—C6—C7—C8178.8 (3)C15—C13—C14—C858.9 (4)
C11—C6—C7—C859.0 (3)C12—C13—C14—C861.0 (4)
C12—C6—C7—C859.0 (3)C9—C8—C14—C1359.6 (4)
C6—C7—C8—C960.3 (4)C7—C8—C14—C1361.1 (4)
C6—C7—C8—C1460.5 (4)C9—C10—C15—C1359.7 (3)
C14—C8—C9—C1060.2 (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—C1061.0 (3)
C8—C9—C10—C1160.1 (4)O1—C5—N1—C12.9 (5)
C9—C10—C11—C660.4 (3)C6—C5—N1—C1176.1 (3)
C15—C10—C11—C660.2 (3)C2—C1—N1—C5115.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.991.962.896 (3)158
Symmetry code: (i) x, y, z1/2.

Experimental details

Crystal data
Chemical formulaC15H25NO
Mr235.36
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)32.257 (7), 9.4353 (19), 9.5328 (19)
β (°) 101.69 (3)
V3)2841.1 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14458, 3260, 1544
Rint0.077
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.086, 0.246, 1.04
No. of reflections3260
No. of parameters155
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.32

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.991.962.896 (3)158
Symmetry code: (i) x, y, z1/2.
 

Acknowledgements

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

References

First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSiMa, W. (2009). Acta Cryst. E65, o2452.  Web of Science CSD CrossRef IUCr Journals
First citationTadashi, X. & Sasaki, Y. (1969). Bull. Chem. Soc. Jpn, 42, 1617–1621.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds