N-(4-Hy-droxy-phen-yl)-3,4,5-trimeth-oxy-benzamide.

In the title amide compound, C(16)H(17)NO(5), the dihedral angle between the benzene rings is 71.59 (4)°. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional array parallel to the ab plane.

Related literature

For general background to tyrosinase and melanin, see: Kubo et al. (2000 ▶); Nerya et al. (2004 ▶). For the development of potent inhibitory agents of tyrosinase, see: Cabanes et al. (1994 ▶); Casanola-Martin et al. (2006 ▶); Thanigaimalai et al. (2010 ▶).

Experimental

Crystal data

C16H17NO5

M = 303.31

Orthorhombic,

a = 10.4280 (5) Å

b = 13.4075 (6) Å

c = 21.5565 (8) Å

V = 3013.9 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.1 mm−1

T = 296 K

0.23 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

14730 measured reflections

3459 independent reflections

2086 reflections with I > 2σ(I)

R int = 0.130

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.134

S = 0.97

3459 reflections

207 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.29 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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040554/is2785sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040554/is2785Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040554/is2785Isup3.cml

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

C16H17NO5	F(000) = 1280
Mr = 303.31	Dx = 1.337 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3298 reflections
a = 10.4280 (5) Å	θ = 2.7–25.0°
b = 13.4075 (6) Å	µ = 0.1 mm−1
c = 21.5565 (8) Å	T = 296 K
V = 3013.9 (2) Å3	Block, colourless
Z = 8	0.23 × 0.16 × 0.08 mm

Bruker SMART CCD area-detector diffractometer	Rint = 0.130
graphite	θmax = 27.5°, θmin = 2.7°
φ and ω scans	h = −13→10
14730 measured reflections	k = −14→17
3459 independent reflections	l = −11→27
2086 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0597P)2] where P = (Fo2 + 2Fc2)/3
3459 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.29 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	0.09766 (17)	0.55474 (11)	0.38891 (8)	0.0352 (4)
C2	0.09088 (17)	0.65316 (11)	0.36913 (8)	0.0352 (4)
H2	0.0367	0.671	0.3367	0.042*
C3	0.16570 (17)	0.72450 (11)	0.39825 (8)	0.0330 (4)
C4	0.24487 (18)	0.69932 (11)	0.44779 (8)	0.0355 (4)
C5	0.2478 (2)	0.60042 (11)	0.46863 (8)	0.0387 (4)
C6	0.17580 (19)	0.52861 (12)	0.43820 (8)	0.0391 (5)
H6	0.18	0.4624	0.451	0.047*
C7	0.01230 (19)	0.48017 (12)	0.35789 (8)	0.0379 (4)
O8	−0.09130 (14)	0.50472 (9)	0.33584 (7)	0.0557 (4)
N9	0.05744 (18)	0.38648 (10)	0.35655 (8)	0.0435 (4)
H9	0.139 (2)	0.3796 (14)	0.3652 (9)	0.058 (7)*
C10	−0.00908 (19)	0.29931 (12)	0.33568 (8)	0.0376 (4)
C11	0.06275 (19)	0.22529 (12)	0.30716 (8)	0.0407 (4)
H11	0.149	0.236	0.2986	0.049*
C12	0.0057 (2)	0.13529 (12)	0.29149 (8)	0.0421 (5)
H12	0.0544	0.0854	0.273	0.051*
C13	−0.1220 (2)	0.11949 (12)	0.30309 (8)	0.0417 (5)
C14	−0.1944 (2)	0.19343 (13)	0.33081 (9)	0.0469 (5)
H14	−0.2812	0.1831	0.3383	0.056*
C15	−0.1375 (2)	0.28301 (13)	0.34741 (9)	0.0471 (5)
H15	−0.1862	0.3324	0.3665	0.057*
O16	−0.17129 (17)	0.02840 (9)	0.28685 (8)	0.0596 (5)
H16	−0.251 (4)	0.023 (2)	0.2997 (14)	0.116 (12)*
O17	0.16842 (13)	0.82370 (8)	0.38183 (6)	0.0436 (3)
C18	0.0830 (3)	0.85680 (15)	0.33432 (11)	0.0723 (7)
H18A	0.0951	0.9269	0.3274	0.108*
H18B	−0.0039	0.8447	0.3469	0.108*
H18C	0.1004	0.821	0.2967	0.108*
O19	0.30929 (14)	0.77608 (8)	0.47554 (6)	0.0524 (4)
C20	0.4380 (2)	0.76199 (16)	0.49453 (12)	0.0715 (7)
H20A	0.4698	0.8224	0.5128	0.107*
H20B	0.4896	0.745	0.4592	0.107*
H20C	0.4419	0.709	0.5244	0.107*
O21	0.32026 (16)	0.58220 (8)	0.52010 (6)	0.0580 (4)
C22	0.3337 (3)	0.48202 (14)	0.54042 (11)	0.0732 (8)
H22A	0.3862	0.4802	0.577	0.11*
H22B	0.3733	0.4432	0.5083	0.11*
H22C	0.2507	0.4549	0.5497	0.11*

	U11	U22	U33	U12	U13	U23
C1	0.0363 (11)	0.0263 (9)	0.0430 (10)	−0.0007 (7)	0.0014 (9)	−0.0003 (7)
C2	0.0353 (11)	0.0306 (9)	0.0396 (9)	0.0020 (7)	0.0002 (8)	0.0028 (7)
C3	0.0354 (10)	0.0234 (8)	0.0401 (9)	0.0021 (7)	0.0037 (8)	0.0033 (7)
C4	0.0389 (11)	0.0266 (8)	0.0409 (10)	−0.0013 (7)	−0.0026 (8)	−0.0033 (7)
C5	0.0446 (12)	0.0319 (9)	0.0397 (10)	0.0024 (8)	−0.0066 (9)	0.0024 (7)
C6	0.0453 (12)	0.0249 (9)	0.0470 (11)	0.0020 (7)	−0.0027 (9)	0.0030 (7)
C7	0.0368 (12)	0.0307 (10)	0.0462 (10)	−0.0018 (7)	−0.0028 (9)	0.0046 (7)
O8	0.0433 (9)	0.0392 (7)	0.0847 (11)	−0.0009 (6)	−0.0179 (8)	0.0071 (6)
N9	0.0376 (10)	0.0280 (8)	0.0648 (11)	−0.0005 (7)	−0.0098 (9)	−0.0062 (6)
C10	0.0405 (12)	0.0289 (9)	0.0434 (10)	−0.0031 (7)	−0.0049 (9)	−0.0007 (7)
C11	0.0345 (11)	0.0392 (10)	0.0484 (11)	−0.0028 (8)	−0.0007 (9)	−0.0019 (8)
C12	0.0455 (12)	0.0350 (10)	0.0458 (11)	−0.0004 (8)	0.0019 (9)	−0.0071 (8)
C13	0.0486 (13)	0.0320 (10)	0.0445 (10)	−0.0083 (8)	0.0010 (10)	−0.0025 (7)
C14	0.0375 (12)	0.0407 (11)	0.0626 (13)	−0.0059 (8)	0.0056 (10)	−0.0013 (9)
C15	0.0431 (12)	0.0328 (10)	0.0653 (13)	−0.0001 (8)	0.0035 (11)	−0.0067 (8)
O16	0.0579 (11)	0.0425 (8)	0.0784 (11)	−0.0177 (7)	0.0125 (9)	−0.0186 (7)
O17	0.0488 (9)	0.0251 (6)	0.0571 (8)	−0.0018 (5)	−0.0083 (7)	0.0092 (5)
C18	0.0845 (19)	0.0405 (12)	0.0918 (17)	−0.0007 (11)	−0.0379 (15)	0.0227 (11)
O19	0.0577 (10)	0.0328 (7)	0.0666 (9)	−0.0043 (6)	−0.0216 (7)	−0.0053 (6)
C20	0.0641 (17)	0.0598 (14)	0.0906 (17)	−0.0157 (11)	−0.0370 (15)	0.0139 (12)
O21	0.0823 (12)	0.0352 (7)	0.0564 (8)	−0.0025 (7)	−0.0279 (8)	0.0102 (6)
C22	0.105 (2)	0.0445 (13)	0.0700 (15)	0.0016 (12)	−0.0323 (16)	0.0168 (10)

C1—C6	1.384 (2)	C12—C13	1.371 (3)
C1—C2	1.389 (2)	C12—H12	0.93
C1—C7	1.496 (2)	C13—O16	1.371 (2)
C2—C3	1.385 (2)	C13—C14	1.382 (3)
C2—H2	0.93	C14—C15	1.386 (2)
C3—O17	1.3766 (17)	C14—H14	0.93
C3—C4	1.391 (2)	C15—H15	0.93
C4—O19	1.3670 (19)	O16—H16	0.88 (4)
C4—C5	1.400 (2)	O17—C18	1.428 (2)
C5—O21	1.364 (2)	C18—H18A	0.96
C5—C6	1.386 (2)	C18—H18B	0.96
C6—H6	0.93	C18—H18C	0.96
C7—O8	1.225 (2)	O19—C20	1.416 (3)
C7—N9	1.342 (2)	C20—H20A	0.96
N9—C10	1.432 (2)	C20—H20B	0.96
N9—H9	0.87 (2)	C20—H20C	0.96
C10—C15	1.381 (3)	O21—C22	1.420 (2)
C10—C11	1.387 (2)	C22—H22A	0.96
C11—C12	1.387 (2)	C22—H22B	0.96
C11—H11	0.93	C22—H22C	0.96
C6—C1—C2	120.41 (15)	C11—C12—H12	119.8
C6—C1—C7	121.60 (15)	O16—C13—C12	117.10 (17)
C2—C1—C7	117.88 (16)	O16—C13—C14	123.00 (19)
C3—C2—C1	119.24 (16)	C12—C13—C14	119.90 (16)
C3—C2—H2	120.4	C13—C14—C15	119.97 (19)
C1—C2—H2	120.4	C13—C14—H14	120
O17—C3—C2	124.22 (15)	C15—C14—H14	120
O17—C3—C4	114.81 (14)	C10—C15—C14	120.31 (17)
C2—C3—C4	120.97 (14)	C10—C15—H15	119.8
O19—C4—C3	116.41 (14)	C14—C15—H15	119.8
O19—C4—C5	124.17 (16)	C13—O16—H16	110.2 (18)
C3—C4—C5	119.28 (15)	C3—O17—C18	118.15 (14)
O21—C5—C6	124.09 (14)	O17—C18—H18A	109.5
O21—C5—C4	116.28 (15)	O17—C18—H18B	109.5
C6—C5—C4	119.60 (16)	H18A—C18—H18B	109.5
C1—C6—C5	120.43 (15)	O17—C18—H18C	109.5
C1—C6—H6	119.8	H18A—C18—H18C	109.5
C5—C6—H6	119.8	H18B—C18—H18C	109.5
O8—C7—N9	123.53 (17)	C4—O19—C20	119.47 (15)
O8—C7—C1	121.22 (15)	O19—C20—H20A	109.5
N9—C7—C1	115.25 (17)	O19—C20—H20B	109.5
C7—N9—C10	126.95 (18)	H20A—C20—H20B	109.5
C7—N9—H9	115.8 (13)	O19—C20—H20C	109.5
C10—N9—H9	116.8 (13)	H20A—C20—H20C	109.5
C15—C10—C11	119.46 (16)	H20B—C20—H20C	109.5
C15—C10—N9	122.81 (16)	C5—O21—C22	118.36 (14)
C11—C10—N9	117.50 (17)	O21—C22—H22A	109.5
C12—C11—C10	119.92 (18)	O21—C22—H22B	109.5
C12—C11—H11	120	H22A—C22—H22B	109.5
C10—C11—H11	120	O21—C22—H22C	109.5
C13—C12—C11	120.43 (17)	H22A—C22—H22C	109.5
C13—C12—H12	119.8	H22B—C22—H22C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O17i	0.87 (2)	2.18 (2)	3.029 (2)	165.8 (17)
O16—H16···O8ii	0.88 (4)	1.84 (4)	2.710 (2)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O17i	0.87 (2)	2.18 (2)	3.029 (2)	165.8 (17)
O16—H16⋯O8ii	0.88 (4)	1.84 (4)	2.710 (2)	172 (3)

Symmetry codes: (i) ; (ii) .