2-(2,5-Dimeth-oxy-phen-yl)-N-[2-(4-hy-droxy-phen-yl)eth-yl]acetamide.

In the title compound, C(18)H(21)NO(4), the dihedral angles between the acetamide group and the meth-oxy- and hy-droxy-substitured benzene rings are 80.81 (5) and 8.19 (12)°, respectively. The benzene rings are twisted with respect to each other, making a dihedral angle of 72.89 (5)°. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For general background to tyrosinase, see: Kubo et al. (2000 ▶). For the development of tyrosinase inhibitors, see: Lemic-Stojcevic et al. (1995 ▶); Battaini et al. (2000 ▶); Cabanes et al. (1994 ▶); Thanigaimalai et al. (2010 ▶).

Experimental

Crystal data

C18H21NO4

M = 315.36

Orthorhombic,

a = 8.1628 (8) Å

b = 12.0701 (11) Å

c = 17.0176 (16) Å

V = 1676.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.3 × 0.23 × 0.1 mm

Data collection

Bruker SMART CCD area-detector diffractometer

8417 measured reflections

3638 independent reflections

2352 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.088

S = 0.87

3638 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008975/tk5063sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008975/tk5063Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008975/tk5063Isup3.cml

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

C18H21NO4	F(000) = 672
Mr = 315.36	Dx = 1.249 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2320 reflections
a = 8.1628 (8) Å	θ = 2.9–23.6°
b = 12.0701 (11) Å	µ = 0.09 mm−1
c = 17.0176 (16) Å	T = 296 K
V = 1676.7 (3) Å3	Block, colourless
Z = 4	0.3 × 0.23 × 0.1 mm

Bruker SMART CCD area-detector diffractometer	Rint = 0.063
Graphite monochromator	θmax = 27.5°, θmin = 2.8°
φ and ω scans	h = −4→10
8417 measured reflections	k = −15→7
3638 independent reflections	l = −18→21
2352 reflections with I > 2σ(I)

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ2(Fo2) + (0.0365P)2] where P = (Fo2 + 2Fc2)/3
3638 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.12 e Å−3

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
C1	0.4043 (2)	0.70567 (12)	0.09969 (11)	0.0437 (4)
C2	0.2961 (2)	0.62946 (13)	0.13350 (11)	0.0488 (5)
C3	0.2247 (2)	0.54873 (14)	0.08716 (13)	0.0563 (5)
H3	0.153	0.4979	0.1096	0.068*
C4	0.2590 (2)	0.54310 (14)	0.00842 (12)	0.0562 (5)
H4	0.2107	0.4882	−0.0221	0.067*
C5	0.3644 (2)	0.61811 (14)	−0.02606 (12)	0.0516 (5)
C6	0.4357 (2)	0.69979 (13)	0.02022 (11)	0.0472 (5)
H6	0.5056	0.7513	−0.0028	0.057*
C7	0.4814 (2)	0.79400 (13)	0.15008 (11)	0.0475 (5)
H7A	0.396	0.8424	0.1699	0.057*
H7B	0.5543	0.8383	0.1178	0.057*
C8	0.5769 (2)	0.74773 (14)	0.21872 (12)	0.0496 (5)
O9	0.67141 (17)	0.66858 (11)	0.21107 (9)	0.0710 (4)
N10	0.5600 (2)	0.80014 (13)	0.28703 (10)	0.0532 (4)
H10	0.485 (3)	0.8525 (17)	0.2849 (12)	0.073 (7)*
C11	0.6334 (3)	0.76130 (16)	0.35966 (12)	0.0607 (5)
H11A	0.6477	0.8236	0.395	0.073*
H11B	0.741	0.731	0.3484	0.073*
C12	0.5315 (3)	0.67421 (17)	0.39979 (13)	0.0715 (6)
H12A	0.421	0.7022	0.4064	0.086*
H12B	0.5258	0.6094	0.3662	0.086*
C13	0.5972 (2)	0.64031 (15)	0.47870 (12)	0.0544 (5)
C14	0.5678 (3)	0.70159 (14)	0.54505 (13)	0.0630 (6)
H14	0.5077	0.7668	0.5407	0.076*
C15	0.6242 (3)	0.66973 (15)	0.61796 (13)	0.0624 (6)
H15	0.601	0.7126	0.662	0.075*
C16	0.7159 (2)	0.57352 (14)	0.62542 (12)	0.0514 (5)
C17	0.7467 (3)	0.51175 (15)	0.56022 (12)	0.0623 (5)
H17	0.8067	0.4465	0.5645	0.075*
C18	0.6895 (3)	0.54522 (16)	0.48775 (13)	0.0671 (6)
H18	0.7137	0.5026	0.4437	0.081*
O19	0.7706 (2)	0.54495 (11)	0.69866 (9)	0.0700 (4)
H19	0.794 (4)	0.475 (2)	0.7052 (16)	0.139 (12)*
O20	0.26868 (18)	0.64349 (9)	0.21211 (8)	0.0633 (4)
C21	0.1722 (3)	0.56269 (18)	0.25170 (14)	0.0856 (8)
H21A	0.162	0.5826	0.3061	0.128*
H21B	0.2242	0.4916	0.2475	0.128*
H21C	0.0655	0.5594	0.2282	0.128*
O22	0.38811 (19)	0.60474 (12)	−0.10495 (9)	0.0749 (5)
C23	0.4980 (3)	0.6780 (2)	−0.14310 (14)	0.0836 (7)
H23A	0.5043	0.6595	−0.1979	0.125*
H23B	0.6047	0.6714	−0.1198	0.125*
H23C	0.4595	0.7527	−0.1375	0.125*

	U11	U22	U33	U12	U13	U23
C1	0.0431 (10)	0.0391 (8)	0.0488 (13)	0.0005 (8)	−0.0018 (9)	0.0023 (8)
C2	0.0517 (11)	0.0435 (9)	0.0512 (13)	−0.0025 (8)	0.0037 (10)	0.0049 (9)
C3	0.0487 (11)	0.0460 (9)	0.0743 (15)	−0.0108 (9)	0.0024 (11)	0.0050 (10)
C4	0.0532 (12)	0.0503 (10)	0.0651 (15)	−0.0140 (10)	−0.0054 (11)	−0.0081 (9)
C5	0.0463 (10)	0.0565 (10)	0.0521 (14)	−0.0034 (9)	−0.0060 (10)	−0.0046 (9)
C6	0.0427 (10)	0.0465 (9)	0.0523 (13)	−0.0066 (8)	−0.0032 (9)	0.0015 (8)
C7	0.0550 (12)	0.0409 (8)	0.0465 (12)	−0.0047 (8)	0.0034 (9)	0.0004 (8)
C8	0.0484 (11)	0.0423 (8)	0.0582 (14)	−0.0069 (9)	0.0022 (10)	−0.0024 (9)
O9	0.0680 (9)	0.0593 (8)	0.0858 (11)	0.0182 (7)	−0.0068 (8)	−0.0132 (8)
N10	0.0631 (11)	0.0482 (8)	0.0483 (11)	0.0020 (9)	−0.0041 (9)	0.0003 (8)
C11	0.0649 (13)	0.0622 (11)	0.0552 (13)	−0.0086 (10)	−0.0084 (11)	0.0006 (10)
C12	0.0661 (13)	0.0735 (13)	0.0750 (16)	−0.0123 (12)	−0.0153 (12)	0.0217 (11)
C13	0.0456 (11)	0.0557 (10)	0.0618 (14)	−0.0060 (9)	−0.0070 (10)	0.0102 (10)
C14	0.0607 (13)	0.0487 (10)	0.0795 (17)	0.0101 (10)	0.0030 (12)	0.0125 (11)
C15	0.0743 (14)	0.0474 (10)	0.0656 (15)	0.0058 (10)	0.0069 (12)	−0.0013 (10)
C16	0.0557 (12)	0.0453 (9)	0.0532 (13)	−0.0073 (9)	−0.0089 (10)	0.0053 (9)
C17	0.0690 (13)	0.0551 (10)	0.0628 (14)	0.0164 (10)	−0.0085 (13)	−0.0018 (11)
C18	0.0808 (16)	0.0606 (11)	0.0600 (15)	0.0111 (12)	−0.0088 (12)	−0.0068 (11)
O19	0.0949 (11)	0.0539 (8)	0.0611 (10)	−0.0033 (8)	−0.0192 (9)	0.0029 (7)
O20	0.0770 (9)	0.0559 (7)	0.0569 (9)	−0.0153 (7)	0.0127 (8)	0.0061 (7)
C21	0.113 (2)	0.0654 (13)	0.0782 (17)	−0.0159 (14)	0.0298 (15)	0.0162 (12)
O22	0.0808 (11)	0.0891 (10)	0.0548 (10)	−0.0292 (9)	0.0034 (8)	−0.0165 (8)
C23	0.0788 (17)	0.1105 (18)	0.0614 (16)	−0.0286 (15)	0.0078 (13)	−0.0088 (13)

C1—C6	1.378 (2)	C12—H12A	0.97
C1—C2	1.399 (2)	C12—H12B	0.97
C1—C7	1.506 (2)	C13—C14	1.371 (3)
C2—O20	1.367 (2)	C13—C18	1.382 (3)
C2—C3	1.382 (3)	C14—C15	1.378 (3)
C3—C4	1.371 (3)	C14—H14	0.93
C3—H3	0.93	C15—C16	1.387 (3)
C4—C5	1.380 (3)	C15—H15	0.93
C4—H4	0.93	C16—C17	1.360 (3)
C5—O22	1.366 (2)	C16—O19	1.368 (2)
C5—C6	1.390 (2)	C17—C18	1.379 (3)
C6—H6	0.93	C17—H17	0.93
C7—C8	1.511 (3)	C18—H18	0.93
C7—H7A	0.97	O19—H19	0.87 (3)
C7—H7B	0.97	O20—C21	1.423 (2)
C8—O9	1.235 (2)	C21—H21A	0.96
C8—N10	1.331 (2)	C21—H21B	0.96
N10—C11	1.452 (2)	C21—H21C	0.96
N10—H10	0.88 (2)	O22—C23	1.417 (2)
C11—C12	1.504 (3)	C23—H23A	0.96
C11—H11A	0.97	C23—H23B	0.96
C11—H11B	0.97	C23—H23C	0.96
C12—C13	1.503 (3)
C6—C1—C2	119.14 (16)	C11—C12—H12A	108.9
C6—C1—C7	121.17 (15)	C13—C12—H12B	108.9
C2—C1—C7	119.67 (17)	C11—C12—H12B	108.9
O20—C2—C3	125.22 (16)	H12A—C12—H12B	107.7
O20—C2—C1	115.11 (15)	C14—C13—C18	116.86 (18)
C3—C2—C1	119.67 (18)	C14—C13—C12	121.78 (18)
C4—C3—C2	120.45 (17)	C18—C13—C12	121.36 (19)
C4—C3—H3	119.8	C13—C14—C15	122.16 (17)
C2—C3—H3	119.8	C13—C14—H14	118.9
C3—C4—C5	120.68 (17)	C15—C14—H14	118.9
C3—C4—H4	119.7	C14—C15—C16	119.76 (19)
C5—C4—H4	119.7	C14—C15—H15	120.1
O22—C5—C4	115.38 (16)	C16—C15—H15	120.1
O22—C5—C6	125.57 (17)	C17—C16—O19	123.00 (17)
C4—C5—C6	119.05 (18)	C17—C16—C15	118.94 (18)
C1—C6—C5	120.99 (17)	O19—C16—C15	118.06 (19)
C1—C6—H6	119.5	C16—C17—C18	120.41 (18)
C5—C6—H6	119.5	C16—C17—H17	119.8
C1—C7—C8	113.21 (13)	C18—C17—H17	119.8
C1—C7—H7A	108.9	C17—C18—C13	121.8 (2)
C8—C7—H7A	108.9	C17—C18—H18	119.1
C1—C7—H7B	108.9	C13—C18—H18	119.1
C8—C7—H7B	108.9	C16—O19—H19	115.6 (19)
H7A—C7—H7B	107.7	C2—O20—C21	117.97 (15)
O9—C8—N10	121.66 (18)	O20—C21—H21A	109.5
O9—C8—C7	121.78 (18)	O20—C21—H21B	109.5
N10—C8—C7	116.48 (16)	H21A—C21—H21B	109.5
C8—N10—C11	123.19 (17)	O20—C21—H21C	109.5
C8—N10—H10	112.2 (14)	H21A—C21—H21C	109.5
C11—N10—H10	123.7 (14)	H21B—C21—H21C	109.5
N10—C11—C12	112.56 (16)	C5—O22—C23	117.79 (15)
N10—C11—H11A	109.1	O22—C23—H23A	109.5
C12—C11—H11A	109.1	O22—C23—H23B	109.5
N10—C11—H11B	109.1	H23A—C23—H23B	109.5
C12—C11—H11B	109.1	O22—C23—H23C	109.5
H11A—C11—H11B	107.8	H23A—C23—H23C	109.5
C13—C12—C11	113.50 (18)	H23B—C23—H23C	109.5
C13—C12—H12A	108.9

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O19i	0.88 (2)	2.16 (2)	3.023 (2)	165.4 (19)
O19—H19···O9ii	0.87 (3)	1.76 (3)	2.6289 (19)	174 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯O19i	0.88 (2)	2.16 (2)	3.023 (2)	165.4 (19)
O19—H19⋯O9ii	0.87 (3)	1.76 (3)	2.6289 (19)	174 (3)

Symmetry codes: (i) ; (ii) .