N-Butyladamantane-1-carboxamide

SiMa, W.

doi:10.1107/S1600536809036897

organic compounds

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Volume 65| Part 10| October 2009| Page o2492

doi:10.1107/S1600536809036897

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N-Butyladamantane-1-carboxamide

Weiwei SiMa ^a ^*

^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 ). For further synthetic details, see: Tadashi & Sasaki (1969 ).

Experimental

Crystal data

C₁₅H₂₅NO
M_r = 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)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.086
wR(F²) = 0.246
S = 1.04
3260 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

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

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

checkCIF report

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).

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

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

C₁₅H₂₅NO	F(000) = 1040
M_r = 235.36	D_x = 1.100 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4730 reflections
a = 32.257 (7) Å	θ = 3.0–27.8°
b = 9.4353 (19) Å	µ = 0.07 mm⁻¹
c = 9.5328 (19) Å	T = 298 K
β = 101.69 (3)°	Prism, colourless
V = 2841.1 (10) Å³	0.20 × 0.20 × 0.20 mm
Z = 8

Data collection top

Rigaku SCXmini diffractometer	1544 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.077
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
Detector resolution: 13.6612 pixels mm^-1	h = −41→41
ω scans	k = −12→12
14458 measured reflections	l = −12→12
3260 independent reflections

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.246	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0977P)² + 2.030P] where P = (F_o² + 2F_c²)/3
3260 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₅H₂₅NO	V = 2841.1 (10) Å³
M_r = 235.36	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 32.257 (7) Å	µ = 0.07 mm⁻¹
b = 9.4353 (19) Å	T = 298 K
c = 9.5328 (19) Å	0.20 × 0.20 × 0.20 mm
β = 101.69 (3)°

Data collection top

Rigaku SCXmini diffractometer	1544 reflections with I > 2σ(I)
14458 measured reflections	R_int = 0.077
3260 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.086	0 restraints
wR(F²) = 0.246	H-atom parameters constrained
S = 1.04	Δρ_max = 0.36 e Å⁻³
3260 reflections	Δρ_min = −0.32 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.30657 (10)	−0.1173 (4)	0.4805 (4)	0.0671 (10)
H1A	0.3025	−0.1014	0.5774	0.080*
H1B	0.3146	−0.2157	0.4733	0.080*
C2	0.26562 (13)	−0.0911 (5)	0.3781 (5)	0.0935 (13)
H2A	0.2702	−0.1038	0.2813	0.112*
H2B	0.2453	−0.1622	0.3941	0.112*
C3	0.24721 (15)	0.0484 (6)	0.3883 (7)	0.143 (2)
H3A	0.2643	0.1164	0.3488	0.172*
H3B	0.2502	0.0705	0.4892	0.172*
C4	0.20314 (15)	0.0729 (6)	0.3200 (7)	0.152 (2)
H4A	0.1997	0.0609	0.2183	0.229*
H4B	0.1952	0.1677	0.3403	0.229*
H4C	0.1854	0.0065	0.3564	0.229*
C5	0.36027 (8)	0.0693 (3)	0.5470 (3)	0.0431 (7)
C6	0.39355 (8)	0.1604 (3)	0.4964 (3)	0.0411 (7)
C7	0.41628 (10)	0.2560 (4)	0.6189 (3)	0.0615 (9)
H7A	0.3957	0.3154	0.6524	0.074*
H7B	0.4303	0.1979	0.6984	0.074*
C8	0.44885 (11)	0.3491 (4)	0.5667 (4)	0.0715 (10)
H8	0.4630	0.4095	0.6456	0.086*
C9	0.48163 (10)	0.2564 (4)	0.5166 (4)	0.0795 (11)
H9A	0.5025	0.3155	0.4844	0.095*
H9B	0.4961	0.1981	0.5952	0.095*
C10	0.45958 (10)	0.1630 (4)	0.3948 (4)	0.0614 (9)
H10	0.4806	0.1031	0.3624	0.074*
C11	0.42699 (9)	0.0688 (3)	0.4458 (3)	0.0525 (8)
H11A	0.4411	0.0091	0.5238	0.063*
H11B	0.4134	0.0078	0.3680	0.063*
C12	0.37184 (9)	0.2551 (3)	0.3720 (3)	0.0513 (8)
H12A	0.3576	0.1965	0.2932	0.062*
H12B	0.3507	0.3140	0.4030	0.062*
C13	0.40482 (11)	0.3492 (3)	0.3218 (3)	0.0619 (9)
H13	0.3907	0.4089	0.2422	0.074*
C14	0.42639 (12)	0.4422 (4)	0.4441 (4)	0.0773 (11)
H14A	0.4056	0.5012	0.4765	0.093*
H14B	0.4467	0.5036	0.4121	0.093*
C15	0.43746 (11)	0.2543 (4)	0.2710 (3)	0.0674 (10)
H15A	0.4234	0.1945	0.1929	0.081*
H15B	0.4581	0.3125	0.2364	0.081*
N1	0.34081 (7)	−0.0273 (3)	0.4547 (2)	0.0582 (7)
H1C	0.3501	−0.0278	0.3622	0.070*
O1	0.35154 (7)	0.0859 (2)	0.6660 (2)	0.0619 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.062 (2)	0.075 (2)	0.065 (2)	−0.0255 (18)	0.0153 (18)	0.0110 (18)
C2	0.074 (3)	0.087 (3)	0.123 (4)	−0.018 (2)	0.028 (3)	0.022 (3)
C3	0.086 (3)	0.105 (4)	0.244 (7)	0.001 (3)	0.044 (4)	0.024 (4)
C4	0.085 (4)	0.126 (5)	0.245 (8)	0.003 (3)	0.030 (4)	0.008 (5)
C5	0.0435 (16)	0.0514 (18)	0.0365 (14)	0.0034 (13)	0.0128 (13)	0.0079 (13)
C6	0.0425 (15)	0.0466 (16)	0.0357 (14)	−0.0005 (12)	0.0111 (12)	−0.0016 (12)
C7	0.069 (2)	0.072 (2)	0.0451 (17)	−0.0157 (18)	0.0151 (15)	−0.0170 (15)
C8	0.076 (2)	0.078 (2)	0.061 (2)	−0.032 (2)	0.0136 (19)	−0.0210 (19)
C9	0.055 (2)	0.098 (3)	0.085 (3)	−0.029 (2)	0.0109 (19)	−0.003 (2)
C10	0.0479 (17)	0.071 (2)	0.072 (2)	−0.0038 (16)	0.0278 (17)	−0.0084 (18)
C11	0.0473 (16)	0.0553 (19)	0.0565 (18)	0.0001 (14)	0.0142 (14)	0.0015 (14)
C12	0.0528 (17)	0.0508 (18)	0.0497 (17)	−0.0002 (14)	0.0090 (14)	0.0037 (14)
C13	0.070 (2)	0.056 (2)	0.060 (2)	−0.0064 (16)	0.0150 (17)	0.0139 (16)
C14	0.093 (3)	0.050 (2)	0.094 (3)	−0.0227 (19)	0.032 (2)	−0.0086 (19)
C15	0.070 (2)	0.081 (2)	0.059 (2)	−0.0260 (19)	0.0307 (17)	−0.0057 (18)
N1	0.0609 (16)	0.0749 (18)	0.0441 (13)	−0.0258 (14)	0.0234 (12)	−0.0055 (13)
O1	0.0715 (15)	0.0796 (16)	0.0407 (11)	−0.0063 (12)	0.0263 (11)	0.0002 (11)

Geometric parameters (Å, º) top

C1—N1	1.453 (4)	C8—C9	1.522 (5)
C1—C2	1.496 (5)	C8—C14	1.523 (5)
C1—H1A	0.9700	C8—H8	0.9800
C1—H1B	0.9700	C9—C10	1.516 (5)
C2—C3	1.456 (6)	C9—H9A	0.9700
C2—H2A	0.9700	C9—H9B	0.9700
C2—H2B	0.9700	C10—C15	1.517 (5)
C3—C4	1.457 (6)	C10—C11	1.529 (4)
C3—H3A	0.9700	C10—H10	0.9800
C3—H3B	0.9700	C11—H11A	0.9700
C4—H4A	0.9600	C11—H11B	0.9700
C4—H4B	0.9600	C12—C13	1.535 (4)
C4—H4C	0.9600	C12—H12A	0.9700
C5—O1	1.232 (3)	C12—H12B	0.9700
C5—N1	1.333 (3)	C13—C14	1.512 (4)
C5—C6	1.527 (4)	C13—C15	1.533 (5)
C6—C11	1.535 (4)	C13—H13	0.9800
C6—C12	1.536 (4)	C14—H14A	0.9700
C6—C7	1.539 (4)	C14—H14B	0.9700
C7—C8	1.528 (4)	C15—H15A	0.9700
C7—H7A	0.9700	C15—H15B	0.9700
C7—H7B	0.9700	N1—H1C	0.9861

N1—C1—C2	113.2 (3)	C10—C9—C8	109.1 (3)
N1—C1—H1A	108.9	C10—C9—H9A	109.9
C2—C1—H1A	108.9	C8—C9—H9A	109.9
N1—C1—H1B	108.9	C10—C9—H9B	109.9
C2—C1—H1B	108.9	C8—C9—H9B	109.9
H1A—C1—H1B	107.8	H9A—C9—H9B	108.3
C3—C2—C1	115.1 (4)	C9—C10—C15	109.8 (3)
C3—C2—H2A	108.5	C9—C10—C11	109.9 (3)
C1—C2—H2A	108.5	C15—C10—C11	109.4 (3)
C3—C2—H2B	108.5	C9—C10—H10	109.2
C1—C2—H2B	108.5	C15—C10—H10	109.2
H2A—C2—H2B	107.5	C11—C10—H10	109.2
C2—C3—C4	119.2 (5)	C10—C11—C6	110.2 (2)
C2—C3—H3A	107.5	C10—C11—H11A	109.6
C4—C3—H3A	107.5	C6—C11—H11A	109.6
C2—C3—H3B	107.5	C10—C11—H11B	109.6
C4—C3—H3B	107.5	C6—C11—H11B	109.6
H3A—C3—H3B	107.0	H11A—C11—H11B	108.1
C3—C4—H4A	109.5	C13—C12—C6	110.0 (2)
C3—C4—H4B	109.5	C13—C12—H12A	109.7
H4A—C4—H4B	109.5	C6—C12—H12A	109.7
C3—C4—H4C	109.5	C13—C12—H12B	109.7
H4A—C4—H4C	109.5	C6—C12—H12B	109.7
H4B—C4—H4C	109.5	H12A—C12—H12B	108.2
O1—C5—N1	122.0 (2)	C14—C13—C15	110.1 (3)
O1—C5—C6	121.7 (3)	C14—C13—C12	109.6 (3)
N1—C5—C6	116.3 (2)	C15—C13—C12	108.9 (3)
C5—C6—C11	111.5 (2)	C14—C13—H13	109.4
C5—C6—C12	109.4 (2)	C15—C13—H13	109.4
C11—C6—C12	108.9 (2)	C12—C13—H13	109.4
C5—C6—C7	110.3 (2)	C13—C14—C8	109.3 (3)
C11—C6—C7	108.2 (2)	C13—C14—H14A	109.8
C12—C6—C7	108.5 (2)	C8—C14—H14A	109.8
C8—C7—C6	110.1 (2)	C13—C14—H14B	109.8
C8—C7—H7A	109.6	C8—C14—H14B	109.8
C6—C7—H7A	109.6	H14A—C14—H14B	108.3
C8—C7—H7B	109.6	C10—C15—C13	109.3 (3)
C6—C7—H7B	109.6	C10—C15—H15A	109.8
H7A—C7—H7B	108.2	C13—C15—H15A	109.8
C9—C8—C14	110.1 (3)	C10—C15—H15B	109.8
C9—C8—C7	109.8 (3)	C13—C15—H15B	109.8
C14—C8—C7	109.3 (3)	H15A—C15—H15B	108.3
C9—C8—H8	109.2	C5—N1—C1	124.1 (2)
C14—C8—H8	109.2	C5—N1—H1C	113.9
C7—C8—H8	109.2	C1—N1—H1C	121.8

N1—C1—C2—C3	−65.2 (5)	C5—C6—C11—C10	179.5 (2)
C1—C2—C3—C4	−165.0 (5)	C12—C6—C11—C10	58.8 (3)
O1—C5—C6—C11	126.9 (3)	C7—C6—C11—C10	−59.0 (3)
N1—C5—C6—C11	−54.1 (3)	C5—C6—C12—C13	179.0 (2)
O1—C5—C6—C12	−112.6 (3)	C11—C6—C12—C13	−58.9 (3)
N1—C5—C6—C12	66.4 (3)	C7—C6—C12—C13	58.6 (3)
O1—C5—C6—C7	6.6 (4)	C6—C12—C13—C14	−60.3 (3)
N1—C5—C6—C7	−174.4 (2)	C6—C12—C13—C15	60.2 (3)
C5—C6—C7—C8	−178.8 (3)	C15—C13—C14—C8	−58.9 (4)
C11—C6—C7—C8	59.0 (3)	C12—C13—C14—C8	61.0 (4)
C12—C6—C7—C8	−59.0 (3)	C9—C8—C14—C13	59.6 (4)
C6—C7—C8—C9	−60.3 (4)	C7—C8—C14—C13	−61.1 (4)
C6—C7—C8—C14	60.5 (4)	C9—C10—C15—C13	−59.7 (3)
C14—C8—C9—C10	−60.2 (4)	C11—C10—C15—C13	61.0 (3)
C7—C8—C9—C10	60.1 (4)	C14—C13—C15—C10	59.2 (3)
C8—C9—C10—C15	60.3 (3)	C12—C13—C15—C10	−61.0 (3)
C8—C9—C10—C11	−60.1 (4)	O1—C5—N1—C1	2.9 (5)
C9—C10—C11—C6	60.4 (3)	C6—C5—N1—C1	−176.1 (3)
C15—C10—C11—C6	−60.2 (3)	C2—C1—N1—C5	115.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1ⁱ	0.99	1.96	2.896 (3)	158

Symmetry code: (i) x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₅NO
M_r	235.36
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	32.257 (7), 9.4353 (19), 9.5328 (19)
β (°)	101.69 (3)
V (Å³)	2841.1 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14458, 3260, 1544
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.086, 0.246, 1.04
No. of reflections	3260
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1ⁱ	0.99	1.96	2.896 (3)	158

Symmetry code: (i) x, −y, z−1/2.

Acknowledgements

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

References

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