N,N-Dicyclo-hexyl-cyclo-hexa-ne-carboxamide.

In the title compound, C(19)H(33)NO, all three cyclo-hexane rings adopt chair conformations. The crystal packing features weak C-H⋯O inter-actions, forming a supra-molecular chain along the c axis.

Related literature

For related studies of N-substituted benzamides, see: Saeed et al. (2011a ▶,b ▶). For a related structure, see: Saeed et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H33NO

M = 291.46

Monoclinic,

a = 9.8237 (3) Å

b = 16.8736 (5) Å

c = 10.8886 (3) Å

β = 102.890 (3)°

V = 1759.42 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.50 mm−1

T = 173 K

0.44 × 0.38 × 0.18 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.940, T max = 1.000

10594 measured reflections

3369 independent reflections

3023 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.05

3369 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027766/tk5114sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027766/tk5114Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027766/tk5114Isup3.cml

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

C19H33NO	F(000) = 648
Mr = 291.46	Dx = 1.100 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 5299 reflections
a = 9.8237 (3) Å	θ = 4.2–71.1°
b = 16.8736 (5) Å	µ = 0.50 mm−1
c = 10.8886 (3) Å	T = 173 K
β = 102.890 (3)°	Chunk, colourless
V = 1759.42 (10) Å3	0.44 × 0.38 × 0.18 mm
Z = 4

Agilent Xcalibur Eos Gemini diffractometer	3369 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3023 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.1500 pixels mm-1	θmax = 71.3°, θmin = 4.6°
ω scans	h = −11→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −20→18
Tmin = 0.940, Tmax = 1.000	l = −13→13
10594 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.073P)2 + 0.3063P] where P = (Fo2 + 2Fc2)/3
3369 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. Agilent Technologies, (2012). CrysAlisPro, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
N1	0.32349 (9)	0.15353 (5)	0.74526 (8)	0.0246 (2)
O1	0.41858 (10)	0.24422 (5)	0.89266 (8)	0.0357 (2)
C1	0.41307 (11)	0.21416 (6)	0.78858 (10)	0.0248 (2)
C2	0.51580 (11)	0.24121 (6)	0.71036 (10)	0.0247 (2)
H2	0.4683	0.2412	0.6211	0.030*
C3	0.63773 (12)	0.18184 (7)	0.73050 (12)	0.0316 (3)
H3A	0.6814	0.1789	0.8195	0.038*
H3B	0.6021	0.1296	0.7032	0.038*
C4	0.74652 (13)	0.20629 (8)	0.65716 (13)	0.0383 (3)
H4A	0.8240	0.1693	0.6747	0.046*
H4B	0.7053	0.2044	0.5675	0.046*
C5	0.80004 (13)	0.28975 (8)	0.69353 (13)	0.0395 (3)
H5A	0.8490	0.2905	0.7814	0.047*
H5B	0.8654	0.3052	0.6430	0.047*
C6	0.67966 (14)	0.34838 (7)	0.67307 (12)	0.0371 (3)
H6A	0.6355	0.3506	0.5841	0.045*
H6B	0.7154	0.4008	0.6992	0.045*
C7	0.57121 (13)	0.32470 (7)	0.74771 (11)	0.0307 (3)
H7A	0.4945	0.3622	0.7312	0.037*
H7B	0.6134	0.3261	0.8372	0.037*
C8	0.29903 (11)	0.12078 (6)	0.61624 (10)	0.0233 (2)
H8	0.3593	0.1500	0.5715	0.028*
C9	0.33861 (12)	0.03328 (7)	0.61448 (11)	0.0292 (3)
H9A	0.2805	0.0024	0.6578	0.035*
H9B	0.4352	0.0263	0.6586	0.035*
C10	0.31939 (13)	0.00374 (7)	0.47898 (12)	0.0340 (3)
H10A	0.3821	0.0323	0.4374	0.041*
H10B	0.3430	−0.0521	0.4795	0.041*
C11	0.16953 (14)	0.01560 (8)	0.40628 (12)	0.0369 (3)
H11A	0.1076	−0.0167	0.4434	0.044*
H11B	0.1606	−0.0014	0.3197	0.044*
C12	0.12716 (15)	0.10224 (8)	0.40858 (12)	0.0381 (3)
H12A	0.0298	0.1079	0.3662	0.046*
H12B	0.1825	0.1337	0.3632	0.046*
C13	0.14821 (12)	0.13330 (7)	0.54369 (11)	0.0286 (3)
H13A	0.1259	0.1893	0.5419	0.034*
H13B	0.0853	0.1058	0.5864	0.034*
C14	0.23915 (12)	0.11819 (6)	0.82848 (10)	0.0257 (3)
H14	0.1855	0.0750	0.7804	0.031*
C15	0.13228 (13)	0.17564 (7)	0.86046 (12)	0.0334 (3)
H15A	0.0738	0.1963	0.7833	0.040*
H15B	0.1803	0.2199	0.9082	0.040*
C16	0.04124 (15)	0.13386 (9)	0.93748 (13)	0.0417 (3)
H16A	−0.0231	0.1717	0.9604	0.050*
H16B	−0.0132	0.0928	0.8866	0.050*
C17	0.12985 (17)	0.09710 (9)	1.05623 (13)	0.0473 (4)
H17A	0.0699	0.0692	1.1015	0.057*
H17B	0.1780	0.1387	1.1106	0.057*
C18	0.23659 (16)	0.03963 (9)	1.02435 (13)	0.0445 (3)
H18A	0.1883	−0.0047	0.9769	0.053*
H18B	0.2947	0.0190	1.1017	0.053*
C19	0.32894 (13)	0.08035 (8)	0.94690 (12)	0.0342 (3)
H19A	0.3852	0.1208	0.9976	0.041*
H19B	0.3915	0.0417	0.9230	0.041*

	U11	U22	U33	U12	U13	U23
N1	0.0262 (5)	0.0280 (5)	0.0215 (5)	−0.0046 (4)	0.0095 (4)	−0.0030 (3)
O1	0.0446 (5)	0.0404 (5)	0.0246 (4)	−0.0135 (4)	0.0129 (4)	−0.0098 (3)
C1	0.0266 (5)	0.0262 (5)	0.0217 (5)	−0.0017 (4)	0.0054 (4)	−0.0009 (4)
C2	0.0260 (5)	0.0269 (5)	0.0213 (5)	−0.0051 (4)	0.0053 (4)	−0.0025 (4)
C3	0.0292 (6)	0.0282 (6)	0.0379 (6)	−0.0031 (5)	0.0087 (5)	−0.0028 (5)
C4	0.0292 (6)	0.0391 (7)	0.0497 (8)	−0.0049 (5)	0.0151 (5)	−0.0089 (6)
C5	0.0312 (6)	0.0454 (7)	0.0439 (7)	−0.0142 (5)	0.0129 (5)	−0.0067 (6)
C6	0.0437 (7)	0.0309 (6)	0.0386 (7)	−0.0138 (5)	0.0133 (5)	−0.0035 (5)
C7	0.0360 (6)	0.0265 (6)	0.0309 (6)	−0.0062 (5)	0.0104 (5)	−0.0038 (4)
C8	0.0249 (5)	0.0251 (5)	0.0214 (5)	−0.0045 (4)	0.0083 (4)	−0.0027 (4)
C9	0.0288 (6)	0.0295 (6)	0.0291 (6)	0.0023 (4)	0.0059 (4)	−0.0039 (4)
C10	0.0374 (7)	0.0314 (6)	0.0344 (7)	−0.0002 (5)	0.0109 (5)	−0.0101 (5)
C11	0.0402 (7)	0.0367 (7)	0.0319 (6)	−0.0079 (5)	0.0039 (5)	−0.0111 (5)
C12	0.0425 (7)	0.0395 (7)	0.0276 (6)	0.0021 (5)	−0.0022 (5)	−0.0024 (5)
C13	0.0301 (6)	0.0276 (6)	0.0273 (6)	0.0012 (4)	0.0050 (5)	−0.0001 (4)
C14	0.0279 (6)	0.0278 (5)	0.0233 (5)	−0.0041 (4)	0.0101 (4)	−0.0010 (4)
C15	0.0339 (6)	0.0362 (6)	0.0345 (6)	0.0019 (5)	0.0171 (5)	0.0011 (5)
C16	0.0394 (7)	0.0505 (8)	0.0424 (7)	−0.0029 (6)	0.0245 (6)	−0.0021 (6)
C17	0.0567 (9)	0.0587 (9)	0.0332 (7)	−0.0126 (7)	0.0242 (6)	0.0014 (6)
C18	0.0524 (8)	0.0470 (8)	0.0359 (7)	−0.0061 (6)	0.0132 (6)	0.0137 (6)
C19	0.0342 (6)	0.0383 (7)	0.0307 (6)	−0.0018 (5)	0.0085 (5)	0.0064 (5)

N1—C1	1.3634 (14)	C10—C11	1.5212 (18)
N1—C8	1.4785 (13)	C10—H10A	0.9700
N1—C14	1.4826 (13)	C10—H10B	0.9700
O1—C1	1.2317 (13)	C11—C12	1.5218 (18)
C1—C2	1.5283 (15)	C11—H11A	0.9700
C2—C7	1.5322 (14)	C11—H11B	0.9700
C2—C3	1.5392 (16)	C12—C13	1.5316 (16)
C2—H2	0.9800	C12—H12A	0.9700
C3—C4	1.5267 (17)	C12—H12B	0.9700
C3—H3A	0.9700	C13—H13A	0.9700
C3—H3B	0.9700	C13—H13B	0.9700
C4—C5	1.5243 (18)	C14—C15	1.5252 (16)
C4—H4A	0.9700	C14—C19	1.5300 (16)
C4—H4B	0.9700	C14—H14	0.9800
C5—C6	1.520 (2)	C15—C16	1.5279 (16)
C5—H5A	0.9700	C15—H15A	0.9700
C5—H5B	0.9700	C15—H15B	0.9700
C6—C7	1.5302 (17)	C16—C17	1.521 (2)
C6—H6A	0.9700	C16—H16A	0.9700
C6—H6B	0.9700	C16—H16B	0.9700
C7—H7A	0.9700	C17—C18	1.524 (2)
C7—H7B	0.9700	C17—H17A	0.9700
C8—C9	1.5279 (15)	C17—H17B	0.9700
C8—C13	1.5302 (15)	C18—C19	1.5323 (17)
C8—H8	0.9800	C18—H18A	0.9700
C9—C10	1.5286 (16)	C18—H18B	0.9700
C9—H9A	0.9700	C19—H19A	0.9700
C9—H9B	0.9700	C19—H19B	0.9700
C1—N1—C8	124.39 (9)	C11—C10—H10B	109.5
C1—N1—C14	119.73 (9)	C9—C10—H10B	109.5
C8—N1—C14	115.84 (8)	H10A—C10—H10B	108.1
O1—C1—N1	121.32 (10)	C10—C11—C12	110.75 (10)
O1—C1—C2	119.40 (10)	C10—C11—H11A	109.5
N1—C1—C2	119.13 (9)	C12—C11—H11A	109.5
C1—C2—C7	111.49 (9)	C10—C11—H11B	109.5
C1—C2—C3	108.41 (9)	C12—C11—H11B	109.5
C7—C2—C3	109.97 (9)	H11A—C11—H11B	108.1
C1—C2—H2	109.0	C11—C12—C13	111.45 (10)
C7—C2—H2	109.0	C11—C12—H12A	109.3
C3—C2—H2	109.0	C13—C12—H12A	109.3
C4—C3—C2	111.28 (10)	C11—C12—H12B	109.3
C4—C3—H3A	109.4	C13—C12—H12B	109.3
C2—C3—H3A	109.4	H12A—C12—H12B	108.0
C4—C3—H3B	109.4	C8—C13—C12	110.87 (10)
C2—C3—H3B	109.4	C8—C13—H13A	109.5
H3A—C3—H3B	108.0	C12—C13—H13A	109.5
C5—C4—C3	110.79 (10)	C8—C13—H13B	109.5
C5—C4—H4A	109.5	C12—C13—H13B	109.5
C3—C4—H4A	109.5	H13A—C13—H13B	108.1
C5—C4—H4B	109.5	N1—C14—C15	113.01 (9)
C3—C4—H4B	109.5	N1—C14—C19	112.78 (9)
H4A—C4—H4B	108.1	C15—C14—C19	111.69 (10)
C6—C5—C4	110.57 (10)	N1—C14—H14	106.2
C6—C5—H5A	109.5	C15—C14—H14	106.2
C4—C5—H5A	109.5	C19—C14—H14	106.2
C6—C5—H5B	109.5	C14—C15—C16	110.43 (10)
C4—C5—H5B	109.5	C14—C15—H15A	109.6
H5A—C5—H5B	108.1	C16—C15—H15A	109.6
C5—C6—C7	111.31 (10)	C14—C15—H15B	109.6
C5—C6—H6A	109.4	C16—C15—H15B	109.6
C7—C6—H6A	109.4	H15A—C15—H15B	108.1
C5—C6—H6B	109.4	C17—C16—C15	111.15 (11)
C7—C6—H6B	109.4	C17—C16—H16A	109.4
H6A—C6—H6B	108.0	C15—C16—H16A	109.4
C6—C7—C2	110.33 (10)	C17—C16—H16B	109.4
C6—C7—H7A	109.6	C15—C16—H16B	109.4
C2—C7—H7A	109.6	H16A—C16—H16B	108.0
C6—C7—H7B	109.6	C16—C17—C18	111.00 (11)
C2—C7—H7B	109.6	C16—C17—H17A	109.4
H7A—C7—H7B	108.1	C18—C17—H17A	109.4
N1—C8—C9	112.66 (9)	C16—C17—H17B	109.4
N1—C8—C13	111.86 (9)	C18—C17—H17B	109.4
C9—C8—C13	110.29 (9)	H17A—C17—H17B	108.0
N1—C8—H8	107.2	C17—C18—C19	111.22 (11)
C9—C8—H8	107.2	C17—C18—H18A	109.4
C13—C8—H8	107.2	C19—C18—H18A	109.4
C8—C9—C10	110.50 (9)	C17—C18—H18B	109.4
C8—C9—H9A	109.6	C19—C18—H18B	109.4
C10—C9—H9A	109.6	H18A—C18—H18B	108.0
C8—C9—H9B	109.6	C14—C19—C18	110.50 (10)
C10—C9—H9B	109.6	C14—C19—H19A	109.6
H9A—C9—H9B	108.1	C18—C19—H19A	109.6
C11—C10—C9	110.87 (10)	C14—C19—H19B	109.6
C11—C10—H10A	109.5	C18—C19—H19B	109.6
C9—C10—H10A	109.5	H19A—C19—H19B	108.1
C8—N1—C1—O1	172.53 (10)	N1—C8—C9—C10	−176.70 (9)
C14—N1—C1—O1	−5.19 (16)	C13—C8—C9—C10	57.54 (12)
C8—N1—C1—C2	−11.91 (16)	C8—C9—C10—C11	−57.93 (13)
C14—N1—C1—C2	170.37 (9)	C9—C10—C11—C12	56.68 (14)
O1—C1—C2—C7	−23.63 (15)	C10—C11—C12—C13	−55.58 (15)
N1—C1—C2—C7	160.73 (10)	N1—C8—C13—C12	177.46 (9)
O1—C1—C2—C3	97.56 (12)	C9—C8—C13—C12	−56.32 (12)
N1—C1—C2—C3	−78.08 (12)	C11—C12—C13—C8	55.60 (14)
C1—C2—C3—C4	−178.71 (9)	C1—N1—C14—C15	65.94 (13)
C7—C2—C3—C4	−56.59 (12)	C8—N1—C14—C15	−111.97 (11)
C2—C3—C4—C5	56.50 (14)	C1—N1—C14—C19	−61.92 (13)
C3—C4—C5—C6	−56.37 (15)	C8—N1—C14—C19	120.17 (10)
C4—C5—C6—C7	57.27 (14)	N1—C14—C15—C16	175.50 (10)
C5—C6—C7—C2	−57.68 (13)	C19—C14—C15—C16	−56.07 (14)
C1—C2—C7—C6	176.91 (9)	C14—C15—C16—C17	56.40 (15)
C3—C2—C7—C6	56.63 (12)	C15—C16—C17—C18	−56.75 (16)
C1—N1—C8—C9	118.68 (11)	C16—C17—C18—C19	56.23 (16)
C14—N1—C8—C9	−63.52 (12)	N1—C14—C19—C18	−175.89 (10)
C1—N1—C8—C13	−116.41 (11)	C15—C14—C19—C18	55.56 (14)
C14—N1—C8—C13	61.39 (12)	C17—C18—C19—C14	−55.32 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.98	2.44	3.3861 (13)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.98	2.44	3.3861 (13)	163

Symmetry code: (i) .