N-Cyclo­hexyl­nicotinamide

Li, N.

doi:10.1107/S1600536810023408

organic compounds

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Volume 66| Part 7| July 2010| Page o1759

doi:10.1107/S1600536810023408

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N-Cyclohexylnicotinamide

Na Li ^a ^*

^aShenyang Research Institute of Chemical Industry, Shenyang 110021, People's Republic of China
^*Correspondence e-mail: joycelina@163.com

(Received 2 June 2010; accepted 17 June 2010; online 23 June 2010)

In the title compound, C₁₂H₁₆N₂O, the dihedral angle between the pyridine ring and C/O/N plane is 22.93 (7)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules, forming extended chains along [001]. π–π interactions between inversion-related pyridine rings [centroid–centroid distance = 3.825 (2)Å] are also observed.

Related literature

For background information on metal-organic framework compounds, see: Subramanian & Zaworotko (1994 ); Kitagawa et al. (2004 ); Rosi et al. (2005 ). For details of the synthesis, see: Basolo et al. (2009 ).

Experimental

Crystal data

C₁₂H₁₆N₂O
M_r = 204.27
Monoclinic, P 2₁ /c
a = 17.596 (2) Å
b = 6.4050 (8) Å
c = 10.1167 (12) Å
β = 103.921 (2)°
V = 1106.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.32 × 0.30 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.869, T_max = 1.000
5389 measured reflections
1956 independent reflections
1661 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 1.06
1956 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.86	2.17	2.9998 (13)	162
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023408/pk2247sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023408/pk2247Isup2.hkl

checkCIF report

Comment top

Metal-organic frameworks (MOFs) have attracted much attention because of their intriguing topologies (Subramanian & Zaworotko,1994; Kitagawa et al., 2004; Rosi et al., 2005). During our efforts to investigate the assembly of metal-organic coordination frameworks, a new compound was generated accidentally and its crystal structure is described in this paper. A dedicated synthesis of the compound was previously described by Basolo et al., (2009). The molecular structure of compound is shown in Fig. 1. The dihedral angle between the mean plane of the pyridine ring and the plane formed by atoms C/O/N is 22.93 (7)°. In the crystal structure N—H···O hydrogen bonds involving the acyl O atoms and the adjacent N—H group, form one-dimensional chains along [001] (Fig. 2). There are also π-π interactions involving inversion related pyridine rings.

Related literature top

For background information on metal-organic framework compounds, see: Subramanian & Zaworotko (1994); Kitagawa et al. (2004); Rosi et al. (2005). For details of the synthesis, see: Basolo et al. (2009).

Experimental top

All the starting materials and solvents for syntheses were obtained commercially and used as received. Zn(OAc)₂.4H₂O (21.8 mg, 0.1 mmol) and N-cyclohexylnicotinamide (20.4 mg, 0.1 mmol) were mixed in a CH₃CN/H₂O (20 ml, 1:1 v/v) solution with vigorous stirring for ca 30 min. The resulting solution was filtered and left to stand at room temperature. Pale-yellow prismatic crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent over a period of 1 week.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability ellipsoids.
	Fig. 2. The one-dimensional chain structure of the title compound, showing N—H···O hydrogen bonds as red dashed lines.

N-cyclohexylnicotinamide top

Crystal data top

C₁₂H₁₆N₂O	F(000) = 440
M_r = 204.27	D_x = 1.226 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2901 reflections
a = 17.596 (2) Å	θ = 2.8–29.5°
b = 6.4050 (8) Å	µ = 0.08 mm⁻¹
c = 10.1167 (12) Å	T = 296 K
β = 103.921 (2)°	Block, pale yellow
V = 1106.7 (2) Å³	0.32 × 0.30 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	1956 independent reflections
Radiation source: fine-focus sealed tube	1661 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.869, T_max = 1.000	k = −7→7
5389 measured reflections	l = −7→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0474P)² + 0.1872P] where P = (F_o² + 2F_c²)/3
1956 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.10 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₂H₁₆N₂O	V = 1106.7 (2) Å³
M_r = 204.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.596 (2) Å	µ = 0.08 mm⁻¹
b = 6.4050 (8) Å	T = 296 K
c = 10.1167 (12) Å	0.32 × 0.30 × 0.22 mm
β = 103.921 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1956 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1661 reflections with I > 2σ(I)
T_min = 0.869, T_max = 1.000	R_int = 0.013
5389 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.06	Δρ_max = 0.10 e Å⁻³
1956 reflections	Δρ_min = −0.17 e Å⁻³
136 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
O1	0.26804 (6)	0.73912 (16)	0.77836 (8)	0.0572 (3)
N1	0.43960 (7)	1.0508 (2)	1.16302 (11)	0.0604 (3)
N2	0.25623 (6)	0.64514 (17)	0.98679 (9)	0.0421 (3)
H2	0.2706	0.6688	1.0729	0.051*
C1	0.36028 (8)	1.0899 (2)	0.89337 (13)	0.0535 (4)
H1	0.3346	1.1024	0.8019	0.064*
C2	0.41240 (9)	1.2403 (2)	0.95508 (15)	0.0620 (4)
H2A	0.4222	1.3564	0.9065	0.074*
C3	0.44952 (8)	1.2162 (2)	1.08908 (15)	0.0597 (4)
H3	0.4835	1.3208	1.1310	0.072*
C4	0.38905 (8)	0.9069 (2)	1.10174 (13)	0.0500 (3)
H4	0.3819	0.7899	1.1518	0.060*
C5	0.34619 (7)	0.9201 (2)	0.96774 (11)	0.0401 (3)
C6	0.28717 (7)	0.7604 (2)	0.90309 (11)	0.0408 (3)
C7	0.19904 (7)	0.48073 (19)	0.93833 (11)	0.0402 (3)
H7	0.2126	0.4131	0.8602	0.048*
C8	0.20335 (8)	0.3175 (2)	1.04845 (13)	0.0479 (3)
H8A	0.1929	0.3827	1.1288	0.057*
H8B	0.2557	0.2590	1.0732	0.057*
C9	0.14451 (9)	0.1438 (2)	1.00039 (15)	0.0572 (4)
H9A	0.1584	0.0687	0.9263	0.069*
H9B	0.1464	0.0462	1.0744	0.069*
C10	0.06238 (9)	0.2285 (2)	0.95261 (14)	0.0556 (4)
H10A	0.0269	0.1151	0.9166	0.067*
H10B	0.0460	0.2884	1.0294	0.067*
C11	0.05771 (8)	0.3929 (2)	0.84404 (13)	0.0543 (4)
H11A	0.0053	0.4511	0.8203	0.065*
H11B	0.0677	0.3288	0.7630	0.065*
C12	0.11653 (7)	0.5674 (2)	0.89148 (13)	0.0482 (3)
H12A	0.1144	0.6650	0.8174	0.058*
H12B	0.1030	0.6423	0.9659	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0711 (6)	0.0719 (7)	0.0293 (5)	−0.0167 (5)	0.0134 (4)	−0.0038 (4)
N1	0.0581 (7)	0.0738 (8)	0.0439 (6)	−0.0118 (6)	0.0014 (5)	−0.0022 (6)
N2	0.0492 (6)	0.0490 (6)	0.0286 (5)	−0.0060 (5)	0.0102 (4)	−0.0030 (4)
C1	0.0543 (8)	0.0661 (9)	0.0378 (7)	−0.0094 (7)	0.0069 (6)	0.0063 (6)
C2	0.0659 (9)	0.0628 (9)	0.0563 (9)	−0.0178 (7)	0.0128 (7)	0.0086 (7)
C3	0.0556 (8)	0.0653 (9)	0.0554 (8)	−0.0164 (7)	0.0079 (7)	−0.0062 (7)
C4	0.0512 (7)	0.0587 (8)	0.0381 (7)	−0.0055 (6)	0.0068 (5)	0.0033 (6)
C5	0.0386 (6)	0.0502 (7)	0.0332 (6)	0.0011 (5)	0.0120 (5)	−0.0004 (5)
C6	0.0429 (7)	0.0490 (7)	0.0316 (6)	0.0017 (5)	0.0110 (5)	−0.0005 (5)
C7	0.0487 (7)	0.0405 (6)	0.0323 (6)	−0.0020 (5)	0.0111 (5)	−0.0045 (5)
C8	0.0562 (8)	0.0439 (7)	0.0421 (7)	0.0049 (6)	0.0090 (6)	0.0033 (6)
C9	0.0818 (10)	0.0390 (7)	0.0517 (8)	−0.0031 (7)	0.0176 (7)	0.0036 (6)
C10	0.0653 (9)	0.0554 (8)	0.0466 (8)	−0.0180 (7)	0.0144 (6)	−0.0041 (6)
C11	0.0544 (8)	0.0589 (9)	0.0455 (7)	−0.0084 (6)	0.0039 (6)	−0.0002 (6)
C12	0.0524 (7)	0.0430 (7)	0.0459 (7)	−0.0009 (6)	0.0054 (6)	0.0047 (6)

Geometric parameters (Å, º) top

O1—C6	1.2328 (14)	C7—C12	1.5196 (17)
N1—C4	1.3262 (17)	C7—H7	0.9800
N1—C3	1.3326 (19)	C8—C9	1.5176 (19)
N2—C6	1.3341 (15)	C8—H8A	0.9700
N2—C7	1.4576 (15)	C8—H8B	0.9700
N2—H2	0.8600	C9—C10	1.510 (2)
C1—C2	1.373 (2)	C9—H9A	0.9700
C1—C5	1.3783 (18)	C9—H9B	0.9700
C1—H1	0.9300	C10—C11	1.5096 (19)
C2—C3	1.365 (2)	C10—H10A	0.9700
C2—H2A	0.9300	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.5203 (18)
C4—C5	1.3863 (17)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.4919 (17)	C12—H12A	0.9700
C7—C8	1.5164 (17)	C12—H12B	0.9700

C4—N1—C3	116.98 (11)	C7—C8—H8A	109.4
C6—N2—C7	122.71 (9)	C9—C8—H8A	109.4
C6—N2—H2	118.6	C7—C8—H8B	109.4
C7—N2—H2	118.6	C9—C8—H8B	109.4
C2—C1—C5	119.59 (12)	H8A—C8—H8B	108.0
C2—C1—H1	120.2	C10—C9—C8	111.48 (11)
C5—C1—H1	120.2	C10—C9—H9A	109.3
C3—C2—C1	118.70 (14)	C8—C9—H9A	109.3
C3—C2—H2A	120.6	C10—C9—H9B	109.3
C1—C2—H2A	120.6	C8—C9—H9B	109.3
N1—C3—C2	123.48 (13)	H9A—C9—H9B	108.0
N1—C3—H3	118.3	C11—C10—C9	111.33 (12)
C2—C3—H3	118.3	C11—C10—H10A	109.4
N1—C4—C5	124.11 (13)	C9—C10—H10A	109.4
N1—C4—H4	117.9	C11—C10—H10B	109.4
C5—C4—H4	117.9	C9—C10—H10B	109.4
C1—C5—C4	117.05 (12)	H10A—C10—H10B	108.0
C1—C5—C6	119.96 (11)	C10—C11—C12	111.68 (10)
C4—C5—C6	122.99 (11)	C10—C11—H11A	109.3
O1—C6—N2	122.41 (11)	C12—C11—H11A	109.3
O1—C6—C5	120.95 (11)	C10—C11—H11B	109.3
N2—C6—C5	116.64 (10)	C12—C11—H11B	109.3
N2—C7—C8	110.04 (9)	H11A—C11—H11B	107.9
N2—C7—C12	111.81 (10)	C7—C12—C11	110.90 (11)
C8—C7—C12	110.86 (10)	C7—C12—H12A	109.5
N2—C7—H7	108.0	C11—C12—H12A	109.5
C8—C7—H7	108.0	C7—C12—H12B	109.5
C12—C7—H7	108.0	C11—C12—H12B	109.5
C7—C8—C9	111.12 (10)	H12A—C12—H12B	108.0

C5—C1—C2—C3	0.5 (2)	C1—C5—C6—N2	−157.12 (12)
C4—N1—C3—C2	−1.9 (2)	C4—C5—C6—N2	23.14 (18)
C1—C2—C3—N1	2.0 (3)	C6—N2—C7—C8	153.38 (11)
C3—N1—C4—C5	−0.6 (2)	C6—N2—C7—C12	−82.96 (14)
C2—C1—C5—C4	−2.8 (2)	N2—C7—C8—C9	−179.80 (10)
C2—C1—C5—C6	177.44 (12)	C12—C7—C8—C9	55.99 (14)
N1—C4—C5—C1	3.0 (2)	C7—C8—C9—C10	−55.68 (15)
N1—C4—C5—C6	−177.30 (12)	C8—C9—C10—C11	54.95 (15)
C7—N2—C6—O1	1.82 (19)	C9—C10—C11—C12	−54.88 (16)
C7—N2—C6—C5	−178.83 (10)	N2—C7—C12—C11	−178.89 (10)
C1—C5—C6—O1	22.24 (18)	C8—C7—C12—C11	−55.69 (14)
C4—C5—C6—O1	−157.50 (13)	C10—C11—C12—C7	55.31 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	2.17	2.9998 (13)	162

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₂O
M_r	204.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	17.596 (2), 6.4050 (8), 10.1167 (12)
β (°)	103.921 (2)
V (Å³)	1106.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.30 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.869, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5389, 1956, 1661
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.06
No. of reflections	1956
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.17

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), 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
N2—H2···O1ⁱ	0.86	2.17	2.9998 (13)	161.5

Symmetry code: (i) x, −y+3/2, z+1/2.

References

Basolo, L., Beccalli, E. M., Borsini, E. & Broggini, G. (2009). Tetrahedron, 65, 3486–3490. Web of Science CrossRef CAS Google Scholar
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Kitagawa, S., Kitaura, T. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334–2375. Web of Science CrossRef CAS Google Scholar
Rosi, N. L., Kim, J., Eddaoudi, M., Chen, B., O'Keeffe, M. & Yaghi, O. M. (2005). J. Am. Chem. Soc. 127, 1504–1518. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1759

doi:10.1107/S1600536810023408

Open

access