N-(2-Oxo-2H-chromen-3-yl)cyclo-hexane-carboxamide.

In the title compound, C16H17NO3, the coumarin moiety is essentially planar [maximum deviation from the mean plane formed by the C and O atoms of the coumarin = 0.0183 (12) Å] and that the cyclo-hexane ring adopts the usual chair conformation. The dihedral angle between the mean plane of the coumarin residue and the plane of the amide residue (defined as the N, C and O atoms) is 18.9 (2)°. There are two intra-molecular hydrogen bonds involving the amide group. In one, the N atom acts as donor to the ketonic O atom and in the other, the amide O atom acts as acceptor of a C-H group of the coumarin. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯O contacts and these dimers are linked into pairs by weak C-H⋯O hydrogen bonds. The combination of these inter-actions creates a chain of rings which runs parallel to [2-10]. C-H⋯π and π-π [centroid-centroid distance = 3.8654 (10) Å] inter-actions are also observed.

Related literature

For the synthesis of the title compound, see: Viña, Matos, Ferino et al. (2012 ▶); Viña, Matos, Yáñez et al. (2012 ▶). For the biological activity of coumarin derivatives, see: Borges et al. (2009 ▶); Matos et al. (2009 ▶, 2010 ▶); Matos, Santana et al. (2011 ▶); Matos, Terán et al. (2011 ▶). For graph-set analysis of n class="Chemical">hydrogen bonds, see: Bernstein et al., (1995 ▶)

Experimental

Crystal data

C16H17NO3

M = 271.31

Triclinic,

a = 6.4486 (6) Å

b = 9.6324 (11) Å

c = 11.0837 (11) Å

α = 83.061 (6)°

β = 89.134 (5)°

γ = 73.987 (5)°

V = 656.79 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.48 × 0.45 × 0.09 mm

Data collection

Bruker X8 APEXII KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.910, T max = 1.000

9698 measured reflections

2487 independent reflections

1834 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.113

S = 1.06

2487 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047903/go2076sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047903/go2076Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047903/go2076Isup3.cml

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

C16H17NO3	F(000) = 288
Mr = 271.31	F(000) = 288
Triclinic, P1	Dx = 1.372 Mg m−3
Hall symbol: -P 1	Melting point: 100 K
a = 6.4486 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6324 (11) Å	Cell parameters from 1680 reflections
c = 11.0837 (11) Å	θ = 2.7–26.3°
α = 83.061 (6)°	µ = 0.10 mm−1
β = 89.134 (5)°	T = 100 K
γ = 73.987 (5)°	Plate, colourless
V = 656.79 (12) Å3	0.48 × 0.45 × 0.09 mm
Z = 2

Bruker X8 APEXII KappaCCD diffractometer	2487 independent reflections
Radiation source: fine-focus sealed tube	1834 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
ω and phi scans	θmax = 25.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −7→7
Tmin = 0.910, Tmax = 1.000	k = −11→11
9698 measured reflections	l = 0→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0577P)2] where P = (Fo2 + 2Fc2)/3
2487 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. 1H NMR (300 MHz, CDCl3): δ 1.27–1.95 (10H, m, 2H-2, 2H-3, 2H-4, 2H-5, 2H-6), 2.33–2.40 (1H, m H-1), 7.25–7.29 (2H, m, H-6, H-8), 7.33 (1H, dd, H-7, J=8.5, J=1.5), 7.46 (1H, dd, H-5, J=8.5, J=1.6), 8.12 (1H, s, H-4), 8.70 (1H, s, –NH); 13C NMR (75.47?MHz, CDCl3): δ 25.6, 25.7, 29.7, 43.0, 116.6, 120.2, 123.4, 124.3, 125.4, 128.0, 129.8, 150.1, 159.2, 175.9; DEPT: 25.6, 25.7, 29.7, 43.0, 116.6, 120.2, 124.3, 125.4, 128.0; MS m/z 272 ([M + 1]+, 16), 271 (M+, 100). Anal. Calcd for C16H17NO3: C, 70.83; H, 6.32. Found: C, 70.85; H, 6.35.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.24398 (15)	0.35744 (12)	−0.13872 (9)	0.0151 (3)
C2	0.2812 (2)	0.23542 (18)	−0.05704 (14)	0.0135 (4)
C3	0.0969 (2)	0.20233 (18)	0.00628 (14)	0.0124 (4)
C4	−0.1049 (2)	0.28990 (18)	−0.01851 (13)	0.0136 (4)
H4	−0.2245	0.2668	0.0216	0.016*
C5	−0.1385 (2)	0.41752 (18)	−0.10531 (13)	0.0128 (4)
C6	−0.3423 (2)	0.51517 (19)	−0.13683 (14)	0.0157 (4)
H6	−0.4679	0.4963	−0.1007	0.019*
C7	−0.3625 (3)	0.63721 (19)	−0.21886 (14)	0.0177 (4)
H7	−0.5009	0.7028	−0.2381	0.021*
C8	−0.1796 (3)	0.66474 (19)	−0.27396 (14)	0.0185 (4)
H8	−0.1938	0.7492	−0.3307	0.022*
C9	0.0224 (3)	0.56983 (18)	−0.24641 (14)	0.0165 (4)
H9	0.1473	0.5875	−0.2843	0.02*
C10	0.0385 (2)	0.44942 (18)	−0.16300 (14)	0.0135 (4)
O11	0.46651 (16)	0.16189 (12)	−0.04220 (10)	0.0183 (3)
N12	0.1571 (2)	0.07624 (16)	0.08823 (12)	0.0147 (3)
H12	0.285 (3)	0.019 (2)	0.0806 (15)	0.028 (5)*
C13	0.0426 (2)	0.03698 (18)	0.18526 (14)	0.0139 (4)
O14	−0.13975 (16)	0.10822 (13)	0.20623 (10)	0.0219 (3)
C15	0.1649 (2)	−0.09965 (18)	0.26441 (14)	0.0131 (4)
H15	0.24	−0.1722	0.2095	0.016*
C16	0.0122 (2)	−0.16661 (18)	0.34364 (14)	0.0160 (4)
H16A	−0.0669	−0.0959	0.3977	0.019*
H16B	−0.0948	−0.1882	0.2911	0.019*
C17	0.1367 (2)	−0.30629 (19)	0.42045 (15)	0.0188 (4)
H17A	0.0353	−0.3448	0.4735	0.023*
H17B	0.2042	−0.3802	0.3664	0.023*
C18	0.3111 (3)	−0.27969 (19)	0.49876 (15)	0.0201 (4)
H18A	0.2425	−0.2148	0.5595	0.024*
H18B	0.3954	−0.3732	0.5431	0.024*
C19	0.4615 (3)	−0.21078 (19)	0.42127 (15)	0.0212 (4)
H19A	0.5427	−0.2807	0.3672	0.025*
H19B	0.567	−0.1889	0.4748	0.025*
C20	0.3377 (2)	−0.07084 (19)	0.34427 (14)	0.0174 (4)
H20A	0.4394	−0.0317	0.292	0.021*
H20B	0.2681	0.0028	0.3981	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0132 (6)	0.0145 (7)	0.0169 (6)	−0.0041 (5)	0.0012 (5)	0.0019 (5)
C2	0.0175 (8)	0.0115 (10)	0.0127 (9)	−0.0048 (7)	0.0005 (7)	−0.0039 (7)
C3	0.0168 (8)	0.0117 (10)	0.0096 (8)	−0.0053 (7)	0.0014 (6)	−0.0015 (7)
C4	0.0145 (8)	0.0160 (10)	0.0117 (9)	−0.0058 (7)	0.0013 (7)	−0.0037 (8)
C5	0.0170 (8)	0.0126 (10)	0.0098 (9)	−0.0048 (7)	0.0007 (7)	−0.0039 (7)
C6	0.0153 (8)	0.0196 (11)	0.0125 (9)	−0.0044 (7)	0.0004 (7)	−0.0043 (8)
C7	0.0199 (9)	0.0175 (10)	0.0133 (9)	0.0000 (7)	−0.0041 (7)	−0.0037 (8)
C8	0.0290 (9)	0.0128 (10)	0.0137 (9)	−0.0060 (8)	−0.0040 (7)	−0.0007 (8)
C9	0.0207 (9)	0.0178 (10)	0.0138 (9)	−0.0099 (7)	0.0015 (7)	−0.0022 (8)
C10	0.0150 (8)	0.0136 (10)	0.0117 (9)	−0.0029 (7)	−0.0016 (6)	−0.0031 (7)
O11	0.0129 (6)	0.0174 (7)	0.0229 (7)	−0.0024 (5)	0.0014 (5)	−0.0005 (5)
N12	0.0126 (7)	0.0145 (8)	0.0149 (8)	−0.0011 (6)	0.0024 (6)	0.0005 (6)
C13	0.0157 (8)	0.0161 (10)	0.0123 (9)	−0.0079 (7)	0.0021 (7)	−0.0036 (7)
O14	0.0162 (6)	0.0218 (8)	0.0230 (7)	−0.0005 (5)	0.0046 (5)	0.0035 (6)
C15	0.0161 (8)	0.0118 (10)	0.0112 (8)	−0.0036 (7)	0.0008 (6)	−0.0014 (7)
C16	0.0182 (8)	0.0169 (10)	0.0148 (9)	−0.0080 (7)	0.0019 (7)	−0.0019 (8)
C17	0.0241 (9)	0.0178 (11)	0.0156 (9)	−0.0083 (7)	0.0029 (7)	−0.0011 (8)
C18	0.0248 (9)	0.0174 (11)	0.0165 (9)	−0.0041 (8)	−0.0006 (7)	0.0003 (8)
C19	0.0213 (9)	0.0221 (11)	0.0194 (10)	−0.0067 (8)	−0.0049 (7)	0.0029 (8)
C20	0.0192 (8)	0.0172 (10)	0.0165 (9)	−0.0075 (7)	−0.0011 (7)	0.0013 (8)

O1—C2	1.3610 (19)	C13—O14	1.2220 (17)
O1—C10	1.3852 (17)	C13—C15	1.514 (2)
C2—O11	1.2115 (17)	C15—C16	1.531 (2)
C2—C3	1.462 (2)	C15—C20	1.537 (2)
C3—C4	1.3523 (19)	C15—H15	1
C3—N12	1.391 (2)	C16—C17	1.526 (2)
C4—C5	1.434 (2)	C16—H16A	0.99
C4—H4	0.95	C16—H16B	0.99
C5—C10	1.389 (2)	C17—C18	1.525 (2)
C5—C6	1.410 (2)	C17—H17A	0.99
C6—C7	1.373 (2)	C17—H17B	0.99
C6—H6	0.95	C18—C19	1.521 (2)
C7—C8	1.395 (2)	C18—H18A	0.99
C7—H7	0.95	C18—H18B	0.99
C8—C9	1.383 (2)	C19—C20	1.527 (2)
C8—H8	0.95	C19—H19A	0.99
C9—C10	1.374 (2)	C19—H19B	0.99
C9—H9	0.95	C20—H20A	0.99
N12—C13	1.370 (2)	C20—H20B	0.99
N12—H12	0.867 (17)
C2—O1—C10	121.98 (12)	C13—C15—C20	111.68 (14)
O11—C2—O1	117.05 (14)	C16—C15—C20	110.15 (13)
O11—C2—C3	124.73 (15)	C13—C15—H15	107.8
O1—C2—C3	118.23 (13)	C16—C15—H15	107.8
C4—C3—N12	127.29 (15)	C20—C15—H15	107.8
C4—C3—C2	120.24 (15)	C17—C16—C15	111.00 (12)
N12—C3—C2	112.46 (13)	C17—C16—H16A	109.4
C3—C4—C5	120.11 (15)	C15—C16—H16A	109.4
C3—C4—H4	119.9	C17—C16—H16B	109.4
C5—C4—H4	119.9	C15—C16—H16B	109.4
C10—C5—C6	116.77 (15)	H16A—C16—H16B	108
C10—C5—C4	119.08 (14)	C18—C17—C16	111.32 (14)
C6—C5—C4	124.15 (15)	C18—C17—H17A	109.4
C7—C6—C5	121.11 (15)	C16—C17—H17A	109.4
C7—C6—H6	119.4	C18—C17—H17B	109.4
C5—C6—H6	119.4	C16—C17—H17B	109.4
C6—C7—C8	119.91 (15)	H17A—C17—H17B	108
C6—C7—H7	120	C19—C18—C17	111.01 (14)
C8—C7—H7	120	C19—C18—H18A	109.4
C9—C8—C7	120.39 (16)	C17—C18—H18A	109.4
C9—C8—H8	119.8	C19—C18—H18B	109.4
C7—C8—H8	119.8	C17—C18—H18B	109.4
C10—C9—C8	118.56 (15)	H18A—C18—H18B	108
C10—C9—H9	120.7	C18—C19—C20	111.67 (14)
C8—C9—H9	120.7	C18—C19—H19A	109.3
C9—C10—O1	116.42 (14)	C20—C19—H19A	109.3
C9—C10—C5	123.25 (14)	C18—C19—H19B	109.3
O1—C10—C5	120.33 (15)	C20—C19—H19B	109.3
C13—N12—C3	127.25 (13)	H19A—C19—H19B	107.9
C13—N12—H12	115.9 (12)	C19—C20—C15	110.64 (14)
C3—N12—H12	116.6 (12)	C19—C20—H20A	109.5
O14—C13—N12	122.46 (15)	C15—C20—H20A	109.5
O14—C13—C15	123.73 (14)	C19—C20—H20B	109.5
N12—C13—C15	113.80 (13)	C15—C20—H20B	109.5
C13—C15—C16	111.49 (12)	H20A—C20—H20B	108.1
C10—O1—C2—O11	179.93 (13)	C4—C5—C10—C9	−179.32 (15)
C10—O1—C2—C3	−0.1 (2)	C6—C5—C10—O1	−178.81 (13)
O11—C2—C3—C4	−178.64 (15)	C4—C5—C10—O1	1.3 (2)
O1—C2—C3—C4	1.4 (2)	C4—C3—N12—C13	−21.3 (3)
O11—C2—C3—N12	0.8 (2)	C2—C3—N12—C13	159.30 (15)
O1—C2—C3—N12	−179.14 (13)	C3—N12—C13—O14	5.0 (3)
N12—C3—C4—C5	179.33 (14)	C3—N12—C13—C15	−173.68 (14)
C2—C3—C4—C5	−1.3 (2)	O14—C13—C15—C16	20.2 (2)
C3—C4—C5—C10	0.0 (2)	N12—C13—C15—C16	−161.13 (14)
C3—C4—C5—C6	−179.90 (14)	O14—C13—C15—C20	−103.50 (18)
C10—C5—C6—C7	−1.3 (2)	N12—C13—C15—C20	75.17 (17)
C4—C5—C6—C7	178.56 (15)	C13—C15—C16—C17	178.50 (13)
C5—C6—C7—C8	1.1 (2)	C20—C15—C16—C17	−56.93 (18)
C6—C7—C8—C9	0.0 (2)	C15—C16—C17—C18	56.43 (18)
C7—C8—C9—C10	−0.7 (2)	C16—C17—C18—C19	−55.19 (18)
C8—C9—C10—O1	179.81 (13)	C17—C18—C19—C20	55.31 (19)
C8—C9—C10—C5	0.4 (2)	C18—C19—C20—C15	−56.28 (18)
C2—O1—C10—C9	179.36 (13)	C13—C15—C20—C19	−178.89 (13)
C2—O1—C10—C5	−1.2 (2)	C16—C15—C20—C19	56.65 (17)
C6—C5—C10—C9	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O11	0.87 (2)	2.346 (19)	2.6990 (18)	104.7 (14)
N12—H12···O11i	0.87 (2)	2.098 (18)	2.9303 (16)	160.8 (17)
C4—H4···O14	0.95	2.37	2.9094 (19)	115
C7—H7···O14ii	0.95	2.57	3.473 (2)	158
C16—H16B···Cg1iii	0.99	2.81	3.5732 (17)	134
C17—H17B···Cg2iii	0.99	2.70	3.5876 (19)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the O1/C2–C5/C10 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H12⋯O11	0.87 (2)	2.346 (19)	2.6990 (18)	104.7 (14)
N12—H12⋯O11i	0.87 (2)	2.098 (18)	2.9303 (16)	160.8 (17)
C4—H4⋯O14	0.95	2.37	2.9094 (19)	115
C7—H7⋯O14ii	0.95	2.57	3.473 (2)	158
C16—H16B⋯Cg1iii	0.99	2.81	3.5732 (17)	134
C17—H17B⋯Cg2iii	0.99	2.70	3.5876 (19)	149

Symmetry codes: (i) ; (ii) ; (iii) .