N-Cyclo­hexyl-2-oxo-2H-1-benzo­pyran-3-carbox­amide

Magaña-Vergara, N.E.; Martínez-Martínez, F.J.; Padilla-Martínez, I.I.; Höpfl, H.; García-Báez, E.V.

doi:10.1107/S160053680402851X

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N-Cyclohexyl-2-oxo-2H-1-benzopyran-3-carboxamide

N. E. Magaña-Vergara, F. J. Martínez-Martínez, I. I. Padilla-Martínez, H. Höpfl and E. V. García-Báez

The title compound, C₁₆H₁₇NO₃, crystallizes in the space group P $\overline 1$ , with one molecule in the asymmetric unit. The amide H atom is engaged in an intramolecular N—H

O contact to the O atom of one of the two carbonyl groups. The molecules form centrosymmetric dimers through self-complementary C—H

O hydrogen-bonding interactions defining the R₂²(14)[R₂¹(6)] motif. The supramolecular structure is achieved by aryl C—H

π interactions, as well as face-to-face π–π stacking interactions between lactone and benzenoid rings.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402851X/nc6004sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680402851X/nc6004Isup2.hkl Contains datablock I

CCDC reference: 259572

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.056
wR factor = 0.142
Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 and WinGX2003 (Farrugia, 1999).

N-Cyclohexyl-2-oxo-2H-1-benzopyran-3-carboxamide top

Crystal data top

C₁₆H₁₇NO₃	Z = 2
M_r = 271.31	F(000) = 288
Triclinic, P1	D_x = 1.345 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0870 (14) Å	Cell parameters from 600 reflections
b = 9.529 (2) Å	θ = 20–25°
c = 12.021 (3) Å	µ = 0.09 mm⁻¹
α = 93.682 (4)°	T = 100 K
β = 96.977 (4)°	Block, colorless
γ = 103.543 (4)°	0.43 × 0.41 × 0.03 mm
V = 669.7 (3) Å³

Data collection top

Bruker SMART area-detector diffractometer	R_int = 0.035
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
φ and ω scans	h = −7→7
7666 measured reflections	k = −12→12
2997 independent reflections	l = −15→15
2550 reflections with I > 2σ(I)

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	All H-atom parameters refined
S = 1.10	w = 1/[σ²(F_o²) + (0.0662P)² + 0.1763P] where P = (F_o² + 2F_c²)/3
2997 reflections	(Δ/σ)_max < 0.001
249 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	−0.26356 (19)	0.16633 (12)	0.00991 (10)	0.0181 (3)
O2	−0.2852 (2)	0.31126 (13)	0.15537 (10)	0.0227 (4)
O11	0.36029 (19)	0.58065 (13)	0.12896 (10)	0.0198 (4)
N12	0.0854 (2)	0.53211 (15)	0.24168 (11)	0.0160 (4)
C2	−0.1688 (3)	0.28584 (17)	0.08511 (14)	0.0156 (5)
C3	0.0613 (3)	0.36935 (17)	0.07359 (13)	0.0146 (5)
C4	0.1752 (3)	0.32328 (18)	−0.00581 (14)	0.0148 (5)
C5	0.1924 (3)	0.13624 (19)	−0.15886 (14)	0.0183 (5)
C6	0.0868 (3)	0.00897 (19)	−0.22438 (15)	0.0204 (5)
C7	−0.1365 (3)	−0.06339 (19)	−0.21298 (14)	0.0194 (5)
C8	−0.2550 (3)	−0.00988 (19)	−0.13586 (14)	0.0192 (5)
C9	−0.1458 (3)	0.11797 (18)	−0.06955 (14)	0.0157 (5)
C10	0.0763 (3)	0.19394 (17)	−0.07922 (13)	0.0157 (5)
C11	0.1810 (3)	0.50328 (17)	0.14994 (13)	0.0146 (5)
C13	0.1973 (3)	0.65462 (17)	0.32436 (14)	0.0149 (5)
C14	0.0268 (3)	0.69626 (19)	0.39493 (14)	0.0176 (5)
C15	0.1454 (3)	0.8274 (2)	0.47928 (16)	0.0215 (5)
C16	0.3476 (3)	0.7979 (2)	0.55463 (15)	0.0221 (5)
C17	0.5153 (3)	0.7500 (2)	0.48492 (15)	0.0211 (5)
C18	0.3940 (3)	0.61972 (19)	0.40022 (15)	0.0189 (5)
H4	0.318 (3)	0.373 (2)	−0.0132 (15)	0.016 (5)*
H5	0.345 (3)	0.188 (2)	−0.1631 (15)	0.017 (5)*
H6	0.168 (3)	−0.032 (2)	−0.2772 (17)	0.028 (5)*
H7	−0.203 (3)	−0.150 (2)	−0.2558 (17)	0.023 (5)*
H8	−0.406 (4)	−0.056 (2)	−0.1257 (16)	0.026 (5)*
H12	−0.056 (4)	0.474 (2)	0.2462 (17)	0.033 (6)*
H13	0.255 (3)	0.734 (2)	0.2851 (15)	0.012 (4)*
H14A	−0.101 (3)	0.720 (2)	0.3446 (16)	0.024 (5)*
H14B	−0.043 (3)	0.611 (2)	0.4364 (16)	0.023 (5)*
H15A	0.198 (3)	0.907 (2)	0.4370 (16)	0.023 (5)*
H15B	0.035 (4)	0.854 (2)	0.5235 (17)	0.029 (5)*
H16A	0.430 (3)	0.885 (2)	0.6037 (17)	0.026 (5)*
H16B	0.288 (3)	0.724 (2)	0.6037 (16)	0.022 (5)*
H17A	0.588 (3)	0.831 (2)	0.4416 (16)	0.025 (5)*
H17B	0.640 (4)	0.723 (2)	0.5350 (17)	0.031 (5)*
H18A	0.500 (3)	0.595 (2)	0.3535 (15)	0.019 (5)*
H18B	0.326 (3)	0.536 (2)	0.4427 (17)	0.025 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0161 (6)	0.0171 (6)	0.0184 (6)	−0.0007 (5)	0.0032 (5)	−0.0027 (5)
O2	0.0181 (6)	0.0243 (7)	0.0226 (7)	−0.0015 (5)	0.0076 (5)	−0.0052 (5)
O11	0.0166 (6)	0.0176 (6)	0.0214 (7)	−0.0043 (5)	0.0075 (5)	−0.0040 (5)
N12	0.0140 (7)	0.0165 (7)	0.0152 (7)	−0.0002 (5)	0.0020 (5)	−0.0017 (5)
C2	0.0159 (8)	0.0140 (8)	0.0155 (8)	0.0017 (6)	0.0015 (6)	−0.0002 (6)
C3	0.0138 (8)	0.0139 (8)	0.0151 (8)	0.0018 (6)	0.0016 (6)	0.0014 (6)
C4	0.0119 (8)	0.0144 (8)	0.0171 (8)	0.0009 (6)	0.0019 (6)	0.0022 (6)
C5	0.0170 (8)	0.0196 (9)	0.0176 (9)	0.0039 (7)	0.0020 (7)	−0.0010 (7)
C6	0.0236 (9)	0.0216 (9)	0.0168 (8)	0.0082 (7)	0.0026 (7)	−0.0017 (7)
C7	0.0244 (9)	0.0143 (8)	0.0163 (8)	0.0028 (7)	−0.0034 (7)	−0.0025 (6)
C8	0.0178 (9)	0.0185 (9)	0.0191 (9)	0.0010 (7)	−0.0002 (7)	0.0027 (7)
C9	0.0176 (8)	0.0166 (8)	0.0133 (8)	0.0045 (6)	0.0019 (6)	0.0027 (6)
C10	0.0167 (8)	0.0143 (8)	0.0155 (8)	0.0029 (6)	0.0010 (6)	0.0023 (6)
C11	0.0154 (8)	0.0137 (8)	0.0149 (8)	0.0040 (6)	0.0018 (6)	0.0017 (6)
C13	0.0156 (8)	0.0136 (8)	0.0148 (8)	0.0018 (6)	0.0037 (6)	−0.0004 (6)
C14	0.0130 (8)	0.0213 (9)	0.0179 (8)	0.0043 (7)	0.0017 (7)	−0.0016 (7)
C15	0.0187 (9)	0.0243 (10)	0.0212 (9)	0.0069 (7)	0.0031 (7)	−0.0073 (8)
C16	0.0200 (9)	0.0260 (10)	0.0176 (9)	0.0038 (7)	0.0006 (7)	−0.0063 (8)
C17	0.0148 (8)	0.0241 (9)	0.0228 (9)	0.0051 (7)	−0.0006 (7)	−0.0052 (7)
C18	0.0164 (8)	0.0205 (9)	0.0203 (9)	0.0061 (7)	0.0038 (7)	−0.0030 (7)

Geometric parameters (Å, º) top

O1—C2	1.371 (2)	C15—C16	1.529 (3)
O1—C9	1.380 (2)	C16—C17	1.526 (3)
O2—C2	1.214 (2)	C17—C18	1.533 (3)
O11—C11	1.230 (2)	C4—H4	0.905 (19)
N12—C11	1.350 (2)	C5—H5	0.953 (19)
N12—C13	1.459 (2)	C6—H6	0.967 (19)
N12—H12	0.92 (2)	C7—H7	0.921 (19)
C2—C3	1.467 (3)	C8—H8	0.95 (2)
C3—C11	1.501 (2)	C13—H13	0.938 (19)
C3—C4	1.354 (2)	C14—H14A	1.004 (19)
C4—C10	1.430 (2)	C14—H14B	1.015 (19)
C5—C6	1.376 (3)	C15—H15A	0.955 (19)
C5—C10	1.413 (2)	C15—H15B	0.97 (2)
C6—C7	1.400 (3)	C16—H16A	0.979 (19)
C7—C8	1.383 (3)	C16—H16B	0.980 (19)
C8—C9	1.389 (2)	C17—H17A	1.005 (19)
C9—C10	1.399 (3)	C17—H17B	1.00 (2)
C13—C18	1.528 (3)	C18—H18A	0.964 (19)
C13—C14	1.522 (3)	C18—H18B	1.009 (19)
C14—C15	1.532 (3)

O1···O11ⁱ	3.1448 (18)	C11···H18A	2.881 (18)
O1···C6ⁱⁱ	3.364 (2)	C14···H18A^v	3.092 (19)
O2···N12	2.7426 (19)	C16···H6^vii	2.98 (2)
O11···C4ⁱⁱⁱ	3.317 (2)	C17···H14A^vi	3.097 (19)
O11···C2ⁱ	3.160 (2)	C17···H15B^vi	3.05 (2)
O11···C18	3.234 (2)	C18···H18B^viii	3.072 (19)
O11···O1ⁱ	3.1448 (18)	H4···O11	2.474 (18)
O11···C5ⁱⁱⁱ	3.319 (2)	H4···H5	2.49 (3)
O1···H8^iv	2.64 (2)	H4···O11ⁱⁱⁱ	2.510 (19)
O2···H12	1.99 (2)	H5···H4	2.49 (3)
O2···H8^iv	2.68 (2)	H5···O11ⁱⁱⁱ	2.470 (19)
O11···H13	2.539 (18)	H6···C16^ix	2.98 (2)
O11···H18A	2.714 (18)	H6···H15B^ix	2.52 (3)
O11···H4	2.474 (18)	H6···H16A^ix	2.49 (3)
O11···H4ⁱⁱⁱ	2.510 (19)	H8···O1^iv	2.64 (2)
O11···H5ⁱⁱⁱ	2.470 (19)	H8···O2^iv	2.68 (2)
N12···O2	2.7426 (19)	H8···C2^iv	3.09 (2)
C2···C7ⁱⁱ	3.447 (3)	H12···O2	1.99 (2)
C2···O11ⁱ	3.160 (2)	H12···C2	2.47 (2)
C2···C6ⁱⁱ	3.464 (3)	H12···H14B	2.54 (3)
C2···C11ⁱ	3.574 (2)	H13···O11	2.539 (18)
C3···C7ⁱⁱ	3.547 (3)	H13···H15A	2.49 (3)
C3···C11ⁱ	3.341 (2)	H13···H17A	2.54 (3)
C3···C3ⁱ	3.317 (2)	H14A···C17^v	3.097 (19)
C4···C11ⁱ	3.401 (3)	H14A···H18A^v	2.46 (3)
C4···O11ⁱⁱⁱ	3.317 (2)	H14A···C5ⁱ	2.760 (19)
C5···O11ⁱⁱⁱ	3.319 (2)	H14A···C6ⁱ	3.028 (19)
C6···C2ⁱⁱ	3.464 (3)	H14B···H12	2.54 (3)
C6···O1ⁱⁱ	3.364 (2)	H14B···H18B	2.51 (3)
C7···C3ⁱⁱ	3.547 (3)	H15A···H13	2.49 (3)
C7···C2ⁱⁱ	3.447 (3)	H15B···C17^v	3.05 (2)
C8···C10ⁱⁱ	3.426 (3)	H15B···H6^vii	2.52 (3)
C9···C9ⁱⁱ	3.554 (3)	H15B···H17B^v	2.46 (3)
C10···C8ⁱⁱ	3.426 (3)	H16A···H6^vii	2.49 (3)
C11···C3ⁱ	3.341 (2)	H17A···H13	2.54 (3)
C11···C2ⁱ	3.574 (2)	H17B···H15B^vi	2.46 (3)
C11···C4ⁱ	3.401 (3)	H17B···H18B^viii	2.55 (3)
C14···C17^v	3.552 (3)	H18A···O11	2.714 (18)
C17···C14^vi	3.552 (3)	H18A···C11	2.881 (18)
C18···O11	3.234 (2)	H18A···C14^vi	3.092 (19)
C2···H12	2.47 (2)	H18A···H14A^vi	2.46 (3)
C2···H8^iv	3.09 (2)	H18B···H14B	2.51 (3)
C5···H14Aⁱ	2.760 (19)	H18B···C18^viii	3.072 (19)
C6···H14Aⁱ	3.028 (19)	H18B···H17B^viii	2.55 (3)

C2—O1—C9	122.59 (14)	C10—C5—H5	117.1 (11)
C11—N12—C13	121.00 (14)	C5—C6—H6	120.0 (11)
C13—N12—H12	122.7 (13)	C7—C6—H6	119.8 (11)
C11—N12—H12	116.1 (13)	C6—C7—H7	119.1 (12)
O1—C2—C3	117.46 (15)	C8—C7—H7	119.7 (12)
O2—C2—C3	126.54 (15)	C7—C8—H8	123.5 (12)
O1—C2—O2	116.00 (15)	C9—C8—H8	118.4 (12)
C4—C3—C11	117.93 (16)	N12—C13—H13	107.9 (11)
C2—C3—C4	119.80 (15)	C14—C13—H13	107.9 (11)
C2—C3—C11	122.24 (15)	C18—C13—H13	109.2 (12)
C3—C4—C10	121.39 (17)	C13—C14—H14A	109.8 (11)
C6—C5—C10	120.09 (17)	C13—C14—H14B	109.7 (11)
C5—C6—C7	120.18 (17)	C15—C14—H14A	109.8 (11)
C6—C7—C8	121.20 (16)	C15—C14—H14B	110.0 (11)
C7—C8—C9	118.05 (17)	H14A—C14—H14B	107.3 (15)
O1—C9—C10	120.49 (14)	C14—C15—H15A	107.4 (11)
O1—C9—C8	117.11 (16)	C14—C15—H15B	109.6 (12)
C8—C9—C10	122.38 (16)	C16—C15—H15A	109.6 (11)
C5—C10—C9	118.09 (15)	C16—C15—H15B	111.5 (13)
C4—C10—C9	118.14 (16)	H15A—C15—H15B	107.0 (16)
C4—C10—C5	123.75 (17)	C15—C16—H16A	110.8 (11)
O11—C11—N12	122.51 (15)	C15—C16—H16B	108.2 (11)
O11—C11—C3	120.27 (15)	C17—C16—H16A	108.2 (11)
N12—C11—C3	117.21 (15)	C17—C16—H16B	111.3 (11)
N12—C13—C14	110.73 (14)	H16A—C16—H16B	107.0 (16)
C14—C13—C18	110.28 (14)	C16—C17—H17A	110.4 (11)
N12—C13—C18	110.81 (13)	C16—C17—H17B	110.5 (12)
C13—C14—C15	110.13 (15)	C18—C17—H17A	108.0 (11)
C14—C15—C16	111.47 (15)	C18—C17—H17B	108.9 (11)
C15—C16—C17	111.33 (15)	H17A—C17—H17B	107.9 (16)
C16—C17—C18	111.00 (15)	C13—C18—H18A	108.5 (11)
C13—C18—C17	110.71 (14)	C13—C18—H18B	107.2 (11)
C3—C4—H4	120.7 (12)	C17—C18—H18A	109.9 (11)
C10—C4—H4	117.9 (12)	C17—C18—H18B	108.9 (11)
C6—C5—H5	122.8 (11)	H18A—C18—H18B	111.6 (16)

C9—O1—C2—O2	−175.31 (15)	C6—C5—C10—C9	0.1 (2)
C9—O1—C2—C3	4.3 (2)	C10—C5—C6—C7	0.4 (3)
C2—O1—C9—C8	175.75 (15)	C6—C5—C10—C4	178.29 (16)
C2—O1—C9—C10	−2.5 (2)	C5—C6—C7—C8	−0.4 (3)
C13—N12—C11—O11	−2.9 (2)	C6—C7—C8—C9	−0.1 (3)
C13—N12—C11—C3	176.03 (14)	C7—C8—C9—O1	−177.46 (15)
C11—N12—C13—C14	160.26 (14)	C7—C8—C9—C10	0.7 (3)
C11—N12—C13—C18	−77.04 (19)	C8—C9—C10—C5	−0.7 (3)
O1—C2—C3—C4	−3.0 (2)	C8—C9—C10—C4	−178.99 (16)
O1—C2—C3—C11	179.12 (14)	O1—C9—C10—C4	−0.9 (2)
O2—C2—C3—C4	176.61 (17)	O1—C9—C10—C5	177.41 (15)
O2—C2—C3—C11	−1.3 (3)	N12—C13—C14—C15	−178.56 (14)
C2—C3—C11—N12	10.5 (2)	C14—C13—C18—C17	−58.56 (18)
C4—C3—C11—O11	11.5 (2)	C18—C13—C14—C15	58.43 (18)
C2—C3—C11—O11	−170.59 (16)	N12—C13—C18—C17	178.48 (14)
C2—C3—C4—C10	−0.2 (2)	C13—C14—C15—C16	−56.69 (19)
C11—C3—C4—C10	177.80 (15)	C14—C15—C16—C17	54.7 (2)
C4—C3—C11—N12	−167.44 (15)	C15—C16—C17—C18	−54.2 (2)
C3—C4—C10—C9	2.1 (2)	C16—C17—C18—C13	56.29 (19)
C3—C4—C10—C5	−176.06 (16)	H12—N12—C11—O11	173.6 (15)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z; (iii) −x+1, −y+1, −z; (iv) −x−1, −y, −z; (v) x−1, y, z; (vi) x+1, y, z; (vii) x, y+1, z+1; (viii) −x+1, −y+1, −z+1; (ix) x, y−1, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O2	0.92 (2)	1.99 (2)	2.7426 (19)	138.7 (18)
C4—H4···O11ⁱⁱⁱ	0.905 (19)	2.510 (19)	3.317 (2)	148.7 (15)
C5—H5···O11ⁱⁱⁱ	0.953 (19)	2.470 (19)	3.319 (2)	148.4 (15)

Symmetry code: (iii) −x+1, −y+1, −z.

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