N-Hexyl-3-(4-hy-droxy-3,5-dimeth-oxy-phen-yl)propanamide.

In the title compound, C(17)H(27)NO(4), which is an hydro-sinapic acid derivative with increased lipophilicity conferred by an additional alkyl chain, the central and the hexyl linear chains contain slightly shorter bond lengths [C-N = 1.316 (2) Å; average linear chain C-C = 1.487 (6) Å] than reported average values [Csp(2)-N = 1.334, C-C for CH(2)-CH(2) = 1.524 and 1.513 Å for CH(2)-CH(3)]. The 4-hy-droxy-3,5-dimeth-oxy-phenyl plane [r.m.s. deviation 0.055 (12) Å] makes an angle of 59.89 (5)° with the central plane of the mol-ecule (composed of the N atom, the carbonyl group and the two methyl-ene C atoms linking the carbonyl group and the ring, [r.m.s. deviation 0.0026 (10) Å], which, in turn, makes an angle of 64.24 (13)° with the essentially planar hexyl chain [r.m.s. deviation 0.035 (18) Å]. The N-H group of the amide group is involved in a bifurcated hydrogen bond towards the hy-droxy and one of the meth-oxy O atoms of the 4-hy-droxy-3,5-dimeth-oxy-phenyl substituent of a neighbouring mol-ecule, forming a two-dimensional network in the (100) plane. In addition, the same hy-droxy group acts as a donor towards the carbonyl O atom of another neighbouring mol-ecule, forming chains running along the b axis.

Related literature

For the dependence on their structural characteristics of the anti­cancer activity of phenolic acids and their derivatives, see: Gomes et al. (2003 ▶). For restrictions on protection of lipophilic systems due to the hydro­philic nature of mol­ecules in aqueous media, see: Gao & Hu (2010 ▶). For the synthesis, see: Roleira et al. (2010 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H27NO4

M = 309.40

Monoclinic,

a = 19.1126 (5) Å

b = 8.4086 (2) Å

c = 11.0715 (3) Å

β = 91.5691 (15)°

V = 1778.64 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.34 × 0.26 × 0.19 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.856, T max = 0.865

34604 measured reflections

4259 independent reflections

2478 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.172

S = 0.99

4255 reflections

204 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009) ▶; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019022/bt5889sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019022/bt5889Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019022/bt5889Isup3.cml

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

C17H27NO4	Dx = 1.157 Mg m−3
Mr = 309.40	Melting point: 366.5 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.1126 (5) Å	Cell parameters from 7386 reflections
b = 8.4086 (2) Å	θ = 3.0–23.3°
c = 11.0715 (3) Å	µ = 0.08 mm−1
β = 91.5691 (15)°	T = 293 K
V = 1778.64 (8) Å3	Prism, colourless
Z = 4	0.34 × 0.26 × 0.19 mm
F(000) = 672

Bruker APEX CCD diffractometer	4259 independent reflections
Radiation source: fine-focus sealed tube	2478 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 27.9°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −25→25
Tmin = 0.856, Tmax = 0.865	k = −11→9
34604 measured reflections	l = −12→14

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.094P)2 + 0.1703P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
4255 reflections	Δρmax = 0.19 e Å−3
204 parameters	Δρmin = −0.15 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: 0.014 (3)

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
N	0.75497 (7)	−0.11966 (19)	0.21012 (13)	0.0636 (4)
H10	0.7363	−0.0564	0.2610	0.076*
O3	0.58084 (7)	0.45097 (14)	0.08943 (12)	0.0698 (4)
O4	0.67504 (7)	0.49686 (13)	−0.08385 (10)	0.0651 (4)
H4	0.6877	0.5478	−0.0240	0.098*
O5	0.73329 (7)	0.25857 (15)	−0.19467 (11)	0.0676 (4)
O9	0.73578 (7)	−0.30205 (15)	0.06653 (12)	0.0689 (4)
C1	0.61840 (9)	0.03560 (18)	0.00631 (14)	0.0507 (4)
C2	0.58855 (9)	0.16335 (19)	0.06493 (15)	0.0523 (4)
H2	0.5555	0.1454	0.1236	0.063*
C3	0.60757 (9)	0.31751 (18)	0.03669 (15)	0.0511 (4)
C4	0.65672 (9)	0.34669 (18)	−0.05009 (14)	0.0485 (4)
C5	0.68601 (9)	0.21800 (19)	−0.10955 (14)	0.0510 (4)
C6	0.66706 (9)	0.06345 (19)	−0.08136 (14)	0.0528 (4)
H6	0.6871	−0.0216	−0.1215	0.063*
C7	0.59855 (9)	−0.13192 (19)	0.04171 (16)	0.0585 (5)
H7A	0.6098	−0.2039	−0.0234	0.070*
H7B	0.5484	−0.1368	0.0525	0.070*
C8	0.63594 (9)	−0.18697 (19)	0.15739 (15)	0.0549 (4)
H8A	0.6284	−0.1097	0.2208	0.066*
H8B	0.6161	−0.2874	0.1826	0.066*
C9	0.71300 (9)	−0.20718 (18)	0.14130 (15)	0.0501 (4)
C11	0.83047 (10)	−0.1231 (3)	0.20557 (19)	0.0850 (7)
H11A	0.8472	−0.0163	0.1900	0.102*
H11B	0.8438	−0.1897	0.1385	0.102*
C12	0.86543 (12)	−0.1833 (3)	0.3176 (2)	0.0894 (7)
H12A	0.8501	−0.2916	0.3316	0.107*
H12B	0.8508	−0.1192	0.3852	0.107*
C13	0.94383 (12)	−0.1808 (4)	0.3140 (2)	0.0967 (8)
H13A	0.9580	−0.2479	0.2477	0.116*
H13B	0.9585	−0.0731	0.2959	0.116*
C14	0.98230 (14)	−0.2337 (4)	0.4256 (3)	0.1093 (9)
H14A	0.9668	−0.1695	0.4927	0.131*
H14B	0.9694	−0.3430	0.4420	0.131*
C15	1.05973 (14)	−0.2242 (4)	0.4222 (3)	0.1218 (11)
H15A	1.0751	−0.2876	0.3547	0.146*
H15B	1.0726	−0.1148	0.4064	0.146*
C16	1.09856 (17)	−0.2777 (5)	0.5325 (3)	0.1430 (13)
H16A	1.0904	−0.3891	0.5448	0.215*
H16B	1.0828	−0.2191	0.6009	0.215*
H16C	1.1477	−0.2597	0.5232	0.215*
C33	0.52544 (11)	0.4316 (2)	0.1699 (2)	0.0792 (6)
H33A	0.5415	0.3707	0.2386	0.119*
H33B	0.4874	0.3767	0.1296	0.119*
H33C	0.5098	0.5340	0.1962	0.119*
C55	0.76020 (12)	0.1358 (3)	−0.26704 (19)	0.0827 (6)
H55A	0.7222	0.0765	−0.3033	0.124*
H55B	0.7888	0.0663	−0.2178	0.124*
H55C	0.7879	0.1812	−0.3293	0.124*

	U11	U22	U33	U12	U13	U23
N	0.0518 (10)	0.0748 (10)	0.0642 (9)	−0.0007 (7)	0.0016 (7)	−0.0170 (8)
O3	0.0784 (9)	0.0481 (7)	0.0842 (9)	0.0003 (6)	0.0272 (7)	−0.0118 (6)
O4	0.0938 (10)	0.0483 (7)	0.0537 (7)	−0.0083 (6)	0.0098 (6)	0.0001 (5)
O5	0.0770 (9)	0.0656 (8)	0.0611 (7)	−0.0018 (6)	0.0200 (6)	−0.0086 (6)
O9	0.0729 (9)	0.0600 (8)	0.0742 (8)	−0.0011 (6)	0.0102 (7)	−0.0160 (6)
C1	0.0504 (10)	0.0457 (8)	0.0552 (9)	−0.0015 (7)	−0.0134 (7)	−0.0021 (7)
C2	0.0495 (10)	0.0502 (9)	0.0573 (9)	−0.0036 (7)	0.0020 (8)	−0.0012 (8)
C3	0.0548 (10)	0.0442 (9)	0.0542 (9)	0.0016 (7)	0.0003 (7)	−0.0063 (7)
C4	0.0572 (10)	0.0426 (8)	0.0456 (8)	−0.0020 (7)	−0.0018 (7)	−0.0009 (7)
C5	0.0501 (10)	0.0564 (9)	0.0465 (8)	0.0004 (7)	−0.0017 (7)	−0.0027 (7)
C6	0.0567 (11)	0.0459 (9)	0.0555 (9)	0.0053 (7)	−0.0059 (8)	−0.0087 (7)
C7	0.0545 (11)	0.0464 (9)	0.0740 (11)	−0.0066 (7)	−0.0105 (8)	−0.0046 (8)
C8	0.0560 (11)	0.0468 (9)	0.0619 (10)	−0.0064 (7)	0.0044 (8)	0.0031 (8)
C9	0.0576 (11)	0.0419 (8)	0.0508 (9)	0.0010 (7)	0.0026 (7)	0.0053 (7)
C11	0.0564 (13)	0.1206 (19)	0.0779 (13)	−0.0055 (12)	0.0030 (10)	−0.0124 (13)
C12	0.0622 (14)	0.1089 (18)	0.0967 (16)	−0.0005 (12)	−0.0056 (12)	0.0081 (14)
C13	0.0641 (15)	0.133 (2)	0.0928 (16)	0.0082 (13)	−0.0021 (12)	−0.0075 (15)
C14	0.0774 (18)	0.138 (2)	0.112 (2)	0.0045 (16)	−0.0112 (15)	0.0073 (18)
C15	0.0728 (18)	0.184 (3)	0.108 (2)	0.0236 (18)	−0.0101 (15)	−0.012 (2)
C16	0.104 (2)	0.209 (4)	0.115 (2)	0.016 (2)	−0.0206 (19)	0.005 (2)
C33	0.0720 (14)	0.0728 (13)	0.0943 (14)	−0.0026 (10)	0.0296 (11)	−0.0245 (12)
C55	0.0834 (16)	0.0945 (16)	0.0711 (12)	0.0065 (12)	0.0193 (11)	−0.0207 (12)

N—C9	1.316 (2)	C11—C12	1.482 (3)
N—C11	1.446 (2)	C11—H11A	0.9700
N—H10	0.8600	C11—H11B	0.9700
O3—C3	1.3703 (19)	C12—C13	1.500 (3)
O3—C33	1.412 (2)	C12—H12A	0.9700
O4—C4	1.3653 (19)	C12—H12B	0.9700
O4—H4	0.8200	C13—C14	1.489 (3)
O5—C5	1.367 (2)	C13—H13A	0.9700
O5—C55	1.412 (2)	C13—H13B	0.9700
O9—C9	1.2373 (19)	C14—C15	1.484 (3)
C1—C6	1.383 (2)	C14—H14A	0.9700
C1—C2	1.386 (2)	C14—H14B	0.9700
C1—C7	1.513 (2)	C15—C16	1.481 (4)
C2—C3	1.384 (2)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.384 (2)	C16—H16A	0.9600
C4—C5	1.392 (2)	C16—H16B	0.9600
C5—C6	1.387 (2)	C16—H16C	0.9600
C6—H6	0.9300	C33—H33A	0.9600
C7—C8	1.522 (2)	C33—H33B	0.9600
C7—H7A	0.9700	C33—H33C	0.9600
C7—H7B	0.9700	C55—H55A	0.9600
C8—C9	1.498 (2)	C55—H55B	0.9600
C8—H8A	0.9700	C55—H55C	0.9600
C8—H8B	0.9700
C9—N—C11	124.19 (16)	H11A—C11—H11B	107.7
C9—N—H10	117.9	C11—C12—C13	113.6 (2)
C11—N—H10	117.9	C11—C12—H12A	108.8
C3—O3—C33	117.97 (14)	C13—C12—H12A	108.8
C4—O4—H4	109.5	C11—C12—H12B	108.8
C5—O5—C55	117.83 (15)	C13—C12—H12B	108.8
C6—C1—C2	119.40 (15)	H12A—C12—H12B	107.7
C6—C1—C7	121.18 (15)	C14—C13—C12	116.4 (2)
C2—C1—C7	119.40 (16)	C14—C13—H13A	108.2
C3—C2—C1	120.40 (16)	C12—C13—H13A	108.2
C3—C2—H2	119.8	C14—C13—H13B	108.2
C1—C2—H2	119.8	C12—C13—H13B	108.2
O3—C3—C4	114.75 (14)	H13A—C13—H13B	107.3
O3—C3—C2	124.57 (16)	C15—C14—C13	115.7 (2)
C4—C3—C2	120.68 (15)	C15—C14—H14A	108.4
O4—C4—C3	122.55 (14)	C13—C14—H14A	108.4
O4—C4—C5	118.68 (15)	C15—C14—H14B	108.4
C3—C4—C5	118.68 (14)	C13—C14—H14B	108.4
O5—C5—C6	124.80 (15)	H14A—C14—H14B	107.4
O5—C5—C4	114.47 (14)	C16—C15—C14	116.1 (3)
C6—C5—C4	120.73 (16)	C16—C15—H15A	108.3
C1—C6—C5	120.10 (15)	C14—C15—H15A	108.3
C1—C6—H6	119.9	C16—C15—H15B	108.3
C5—C6—H6	119.9	C14—C15—H15B	108.3
C1—C7—C8	112.70 (13)	H15A—C15—H15B	107.4
C1—C7—H7A	109.1	C15—C16—H16A	109.5
C8—C7—H7A	109.1	C15—C16—H16B	109.5
C1—C7—H7B	109.1	H16A—C16—H16B	109.5
C8—C7—H7B	109.1	C15—C16—H16C	109.5
H7A—C7—H7B	107.8	H16A—C16—H16C	109.5
C9—C8—C7	112.03 (14)	H16B—C16—H16C	109.5
C9—C8—H8A	109.2	O3—C33—H33A	109.5
C7—C8—H8A	109.2	O3—C33—H33B	109.5
C9—C8—H8B	109.2	H33A—C33—H33B	109.5
C7—C8—H8B	109.2	O3—C33—H33C	109.5
H8A—C8—H8B	107.9	H33A—C33—H33C	109.5
O9—C9—N	121.86 (16)	H33B—C33—H33C	109.5
O9—C9—C8	121.18 (15)	O5—C55—H55A	109.5
N—C9—C8	116.96 (15)	O5—C55—H55B	109.5
N—C11—C12	113.90 (19)	H55A—C55—H55B	109.5
N—C11—H11A	108.8	O5—C55—H55C	109.5
C12—C11—H11A	108.8	H55A—C55—H55C	109.5
N—C11—H11B	108.8	H55B—C55—H55C	109.5
C12—C11—H11B	108.8
C6—C1—C2—C3	−0.4 (2)	C2—C1—C6—C5	0.4 (2)
C7—C1—C2—C3	177.97 (15)	C7—C1—C6—C5	−177.97 (14)
C33—O3—C3—C4	173.79 (16)	O5—C5—C6—C1	−179.81 (14)
C33—O3—C3—C2	−6.2 (3)	C4—C5—C6—C1	0.2 (2)
C1—C2—C3—O3	179.82 (15)	C6—C1—C7—C8	99.72 (18)
C1—C2—C3—C4	−0.2 (2)	C2—C1—C7—C8	−78.67 (19)
O3—C3—C4—O4	−2.5 (2)	C1—C7—C8—C9	−67.73 (19)
C2—C3—C4—O4	177.49 (14)	C11—N—C9—O9	0.6 (3)
O3—C3—C4—C5	−179.18 (14)	C11—N—C9—C8	−179.38 (17)
C2—C3—C4—C5	0.8 (2)	C7—C8—C9—O9	−60.08 (19)
C55—O5—C5—C6	6.1 (2)	C7—C8—C9—N	119.90 (16)
C55—O5—C5—C4	−173.98 (16)	C9—N—C11—C12	−115.0 (2)
O4—C4—C5—O5	2.4 (2)	N—C11—C12—C13	−177.8 (2)
C3—C4—C5—O5	179.19 (14)	C11—C12—C13—C14	177.6 (2)
O4—C4—C5—C6	−177.66 (15)	C12—C13—C14—C15	−177.6 (3)
C3—C4—C5—C6	−0.8 (2)	C13—C14—C15—C16	−179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N—H10···O4i	0.86	2.16	2.9655 (19)	155
N—H10···O5i	0.86	2.55	3.244 (2)	138
O4—H4···O9ii	0.82	1.84	2.6216 (17)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H10⋯O4i	0.86	2.16	2.9655 (19)	155
N—H10⋯O5i	0.86	2.55	3.244 (2)	138
O4—H4⋯O9ii	0.82	1.84	2.6216 (17)	158

Symmetry codes: (i) ; (ii) .