N-(4-Butanoyl-3-hy­droxy­phen­yl)butanamide

Yang, M.-M.; Li, F.-S.; Lu, Q.-S.; Wang, H.-W.; Xie, Q.

doi:10.1107/S1600536811001279

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o441

doi:10.1107/S1600536811001279

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N-(4-Butanoyl-3-hydroxyphenyl)butanamide

Ming-Ming Yang,^a Fang-Shi Li,^a ^* Qi-Sheng Lu,^a Hao-Wei Wang ^a and Qing Xie ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: fangshi.li@njut.edu.cn

(Received 14 December 2010; accepted 10 January 2011; online 22 January 2011)

The title compound, C₁₄H₁₉NO₃, was prepared via the intramolecular rearrangement of 3-(butanoylamino)phenyl butanoate in the presence of anhydrous aluminium chloride. The near coplanarity of the aromatic ring, the amide group and the carbonyl group of the butanoyl fragment [N—C—C—C = −179.65 (17) and O—C—C—C = −178.34 (17)°] results from the intramolecular O—H⋯O and C—H⋯O hydrogen bonds. In the crystal, the molecules form a one-dimensional polymeric structure via N—H⋯O interactions between their amide groups.

Related literature

For the synthesis, see: Wang et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₉NO₃
M_r = 249.30
Monoclinic, P 2₁ /n
a = 6.2870 (13) Å
b = 10.008 (2) Å
c = 21.680 (4) Å
β = 97.96 (3)°
V = 1351.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.975, T_max = 0.983
2684 measured reflections
2448 independent reflections
1732 reflections with I > 2σ(I)
R_int = 0.035
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.160
S = 1.00
2448 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.29	3.109 (2)	160
O2—H2A⋯O3	0.82	1.83	2.552 (3)	146
C6—H6A⋯O1	0.93	2.27	2.875 (3)	122
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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 I, global. DOI: 10.1107/S1600536811001279/gk2334sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001279/gk2334Isup2.hkl

checkCIF report

Comment top

The title compound is an important intermediate for the synthesis of an anticoccidial drug Nequinate. It was prepared via intramolecular rearrangement of 3-(butanoylamino)phenyl butanoate in 1,2-dichloroethane in the presence of anhydrous aluminium chloride. We report here the crystal structure of the title compound.

The molecular structure is shown in Fig. 1.

In the crystal, molecules are linked via intermolecular N—H···O hydrogen bond to form chains.

Related literature top

For details of the synthetic procedure, see: Wang et al. (2006).

Experimental top

The title compound (m.p. 381 K) was prepared by a method reported by Wang et al. (2006). The crystals were obtained from methanolic solution by slow evaporation.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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. Molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown by dashed lines.
	Fig. 2. A packing diagram. Hhydrogen bond is shown by dashed lines.

N-(4-Butanoyl-3-hydroxyphenyl)butanamide top

Crystal data top

C₁₄H₁₉NO₃	F(000) = 536
M_r = 249.30	D_x = 1.226 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 381 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.2870 (13) Å	Cell parameters from 25 reflections
b = 10.008 (2) Å	θ = 10–13°
c = 21.680 (4) Å	µ = 0.09 mm⁻¹
β = 97.96 (3)°	T = 293 K
V = 1351.0 (5) Å³	Plate, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1732 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.3°, θ_min = 1.9°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.975, T_max = 0.983	l = −26→25
2684 measured reflections	3 standard reflections every 200 reflections
2448 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.1P)² + 0.080P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2448 reflections	Δρ_max = 0.19 e Å⁻³
164 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (6)

Crystal data top

C₁₄H₁₉NO₃	V = 1351.0 (5) Å³
M_r = 249.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.2870 (13) Å	µ = 0.09 mm⁻¹
b = 10.008 (2) Å	T = 293 K
c = 21.680 (4) Å	0.30 × 0.20 × 0.20 mm
β = 97.96 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1732 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.035
T_min = 0.975, T_max = 0.983	3 standard reflections every 200 reflections
2684 measured reflections	intensity decay: 1%
2448 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.00	Δρ_max = 0.19 e Å⁻³
2448 reflections	Δρ_min = −0.18 e Å⁻³
164 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
N1	0.1152 (3)	0.62012 (16)	0.25206 (8)	0.0443 (5)
H1N	0.1438	0.7034	0.2480	0.053*
O1	0.2269 (3)	0.41334 (15)	0.22806 (8)	0.0653 (5)
O2	−0.3406 (3)	0.31968 (14)	0.34457 (8)	0.0624 (5)
H2A	−0.4387	0.3191	0.3659	0.094*
O3	−0.6164 (3)	0.41920 (16)	0.40749 (9)	0.0686 (5)
C1	0.1729 (6)	0.5577 (3)	0.07966 (14)	0.0959 (10)
H1A	0.1779	0.5148	0.0403	0.144*
H1B	0.1475	0.6515	0.0732	0.144*
H1C	0.0590	0.5196	0.0992	0.144*
C2	0.3834 (5)	0.5374 (2)	0.12083 (11)	0.0668 (7)
H2B	0.4978	0.5753	0.1006	0.080*
H2C	0.4104	0.4423	0.1259	0.080*
C3	0.3882 (4)	0.6008 (2)	0.18464 (11)	0.0547 (6)
H3A	0.5332	0.5959	0.2067	0.066*
H3B	0.3502	0.6945	0.1795	0.066*
C4	0.2373 (3)	0.5346 (2)	0.22330 (10)	0.0445 (5)
C5	−0.0507 (3)	0.59311 (17)	0.28740 (9)	0.0398 (5)
C6	−0.1165 (3)	0.46492 (18)	0.29964 (10)	0.0442 (5)
H6A	−0.0497	0.3914	0.2844	0.053*
C7	−0.2832 (3)	0.44685 (19)	0.33483 (9)	0.0444 (5)
C8	−0.3858 (3)	0.55602 (19)	0.35889 (9)	0.0425 (5)
C9	−0.3162 (3)	0.6842 (2)	0.34437 (9)	0.0453 (5)
H9A	−0.3830	0.7585	0.3589	0.054*
C10	−0.1537 (3)	0.70308 (19)	0.30956 (9)	0.0442 (5)
H10A	−0.1116	0.7892	0.3006	0.053*
C11	−0.5560 (3)	0.5341 (2)	0.39762 (10)	0.0490 (5)
C12	−0.6540 (3)	0.6497 (2)	0.42757 (10)	0.0534 (6)
H12A	−0.7122	0.7119	0.3953	0.064*
H12B	−0.5417	0.6957	0.4547	0.064*
C13	−0.8299 (4)	0.6116 (3)	0.46512 (10)	0.0580 (6)
H13A	−0.7728	0.5484	0.4971	0.070*
H13B	−0.9440	0.5673	0.4380	0.070*
C14	−0.9232 (5)	0.7300 (3)	0.49570 (12)	0.0794 (8)
H14A	−1.0325	0.6996	0.5192	0.119*
H14B	−0.9846	0.7916	0.4642	0.119*
H14C	−0.8115	0.7738	0.5231	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0468 (10)	0.0330 (9)	0.0537 (10)	−0.0018 (7)	0.0090 (8)	0.0002 (7)
O1	0.0714 (11)	0.0388 (9)	0.0915 (13)	0.0046 (7)	0.0315 (10)	−0.0037 (8)
O2	0.0734 (11)	0.0376 (9)	0.0804 (11)	−0.0086 (7)	0.0251 (9)	0.0033 (7)
O3	0.0702 (11)	0.0529 (10)	0.0876 (12)	−0.0110 (8)	0.0286 (10)	0.0042 (8)
C1	0.125 (3)	0.087 (2)	0.0665 (18)	0.0120 (19)	−0.0203 (18)	−0.0066 (15)
C2	0.0887 (18)	0.0555 (14)	0.0596 (15)	0.0114 (13)	0.0224 (14)	0.0024 (12)
C3	0.0519 (13)	0.0520 (13)	0.0619 (14)	−0.0067 (10)	0.0140 (11)	−0.0059 (11)
C4	0.0425 (11)	0.0398 (12)	0.0503 (12)	0.0007 (9)	0.0038 (9)	−0.0037 (9)
C5	0.0397 (11)	0.0354 (10)	0.0423 (11)	−0.0005 (8)	−0.0019 (9)	0.0007 (8)
C6	0.0471 (11)	0.0334 (11)	0.0517 (12)	0.0029 (9)	0.0053 (10)	−0.0021 (9)
C7	0.0499 (12)	0.0332 (10)	0.0482 (12)	−0.0042 (9)	−0.0006 (9)	0.0016 (9)
C8	0.0412 (11)	0.0404 (11)	0.0439 (11)	−0.0033 (9)	−0.0004 (9)	0.0013 (9)
C9	0.0477 (12)	0.0390 (11)	0.0496 (12)	0.0025 (9)	0.0073 (10)	−0.0038 (9)
C10	0.0498 (12)	0.0309 (10)	0.0520 (12)	−0.0022 (9)	0.0070 (10)	0.0006 (9)
C11	0.0460 (12)	0.0486 (13)	0.0505 (12)	−0.0040 (10)	−0.0008 (10)	0.0028 (9)
C12	0.0493 (12)	0.0573 (14)	0.0540 (13)	−0.0039 (10)	0.0087 (10)	−0.0011 (11)
C13	0.0551 (13)	0.0691 (15)	0.0512 (13)	−0.0006 (11)	0.0119 (11)	0.0037 (11)
C14	0.089 (2)	0.084 (2)	0.0723 (17)	−0.0043 (15)	0.0356 (16)	−0.0064 (14)

Geometric parameters (Å, º) top

N1—C4	1.357 (3)	C6—C7	1.390 (3)
N1—C5	1.403 (2)	C6—H6A	0.9300
N1—H1N	0.8600	C7—C8	1.406 (3)
O1—C4	1.221 (2)	C8—C9	1.405 (3)
O2—C7	1.348 (2)	C8—C11	1.466 (3)
O2—H2A	0.8200	C9—C10	1.365 (3)
O3—C11	1.239 (3)	C9—H9A	0.9300
C1—C2	1.504 (4)	C10—H10A	0.9300
C1—H1A	0.9600	C11—C12	1.500 (3)
C1—H1B	0.9600	C12—C13	1.510 (3)
C1—H1C	0.9600	C12—H12A	0.9700
C2—C3	1.519 (3)	C12—H12B	0.9700
C2—H2B	0.9700	C13—C14	1.515 (3)
C2—H2C	0.9700	C13—H13A	0.9700
C3—C4	1.504 (3)	C13—H13B	0.9700
C3—H3A	0.9700	C14—H14A	0.9600
C3—H3B	0.9700	C14—H14B	0.9600
C5—C6	1.385 (2)	C14—H14C	0.9600
C5—C10	1.396 (3)

C4—N1—C5	129.76 (17)	O2—C7—C8	121.95 (19)
C4—N1—H1N	115.1	C6—C7—C8	121.46 (18)
C5—N1—H1N	115.1	C9—C8—C7	116.97 (18)
C7—O2—H2A	109.5	C9—C8—C11	122.65 (18)
C2—C1—H1A	109.5	C7—C8—C11	120.38 (18)
C2—C1—H1B	109.5	C10—C9—C8	122.01 (18)
H1A—C1—H1B	109.5	C10—C9—H9A	119.0
C2—C1—H1C	109.5	C8—C9—H9A	119.0
H1A—C1—H1C	109.5	C9—C10—C5	120.00 (18)
H1B—C1—H1C	109.5	C9—C10—H10A	120.0
C1—C2—C3	112.9 (2)	C5—C10—H10A	120.0
C1—C2—H2B	109.0	O3—C11—C8	120.2 (2)
C3—C2—H2B	109.0	O3—C11—C12	119.15 (19)
C1—C2—H2C	109.0	C8—C11—C12	120.61 (18)
C3—C2—H2C	109.0	C11—C12—C13	114.48 (19)
H2B—C2—H2C	107.8	C11—C12—H12A	108.6
C4—C3—C2	112.88 (19)	C13—C12—H12A	108.6
C4—C3—H3A	109.0	C11—C12—H12B	108.6
C2—C3—H3A	109.0	C13—C12—H12B	108.6
C4—C3—H3B	109.0	H12A—C12—H12B	107.6
C2—C3—H3B	109.0	C12—C13—C14	113.3 (2)
H3A—C3—H3B	107.8	C12—C13—H13A	108.9
O1—C4—N1	123.21 (19)	C14—C13—H13A	108.9
O1—C4—C3	122.04 (19)	C12—C13—H13B	108.9
N1—C4—C3	114.76 (18)	C14—C13—H13B	108.9
C6—C5—C10	119.95 (18)	H13A—C13—H13B	107.7
C6—C5—N1	123.20 (17)	C13—C14—H14A	109.5
C10—C5—N1	116.84 (16)	C13—C14—H14B	109.5
C5—C6—C7	119.58 (18)	H14A—C14—H14B	109.5
C5—C6—H6A	120.2	C13—C14—H14C	109.5
C7—C6—H6A	120.2	H14A—C14—H14C	109.5
O2—C7—C6	116.59 (17)	H14B—C14—H14C	109.5

C1—C2—C3—C4	67.0 (3)	C6—C7—C8—C11	−177.91 (18)
C5—N1—C4—O1	−5.1 (3)	C7—C8—C9—C10	−1.3 (3)
C5—N1—C4—C3	174.86 (19)	C11—C8—C9—C10	178.29 (19)
C2—C3—C4—O1	46.3 (3)	C8—C9—C10—C5	−0.2 (3)
C2—C3—C4—N1	−133.7 (2)	C6—C5—C10—C9	1.4 (3)
C4—N1—C5—C6	1.0 (3)	N1—C5—C10—C9	−179.87 (17)
C4—N1—C5—C10	−177.72 (19)	C9—C8—C11—O3	177.71 (19)
C10—C5—C6—C7	−1.0 (3)	C7—C8—C11—O3	−2.7 (3)
N1—C5—C6—C7	−179.65 (17)	C9—C8—C11—C12	−4.4 (3)
C5—C6—C7—O2	179.43 (17)	C7—C8—C11—C12	175.14 (18)
C5—C6—C7—C8	−0.6 (3)	O3—C11—C12—C13	−3.1 (3)
O2—C7—C8—C9	−178.34 (17)	C8—C11—C12—C13	179.01 (18)
C6—C7—C8—C9	1.7 (3)	C11—C12—C13—C14	179.02 (19)
O2—C7—C8—C11	2.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.29	3.109 (2)	160
O2—H2A···O3	0.82	1.83	2.552 (3)	146
C6—H6A···O1	0.93	2.27	2.875 (3)	122

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉NO₃
M_r	249.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.2870 (13), 10.008 (2), 21.680 (4)
β (°)	97.96 (3)
V (Å³)	1351.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	2684, 2448, 1732
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.160, 1.00
No. of reflections	2448
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), 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—H1N···O1ⁱ	0.86	2.29	3.109 (2)	160
O2—H2A···O3	0.82	1.83	2.552 (3)	146
C6—H6A···O1	0.93	2.27	2.875 (3)	122

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, X. Z., Zhang, S. J., Dai, L. Y. & Chen, Y. Q. (2006). CN Patent No. 173303. Google Scholar