3,4-Dihydroxy-phenyl 3,4,5-trimethoxy-benzoate.

In the title compound, C(16)H(16)O(7), the dihedral angle between the two benzene rings is 82.02 (7)°. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds, which link the mol-ecules into a two-dimensional network.

Related literature

For details of the general background of whitening agents, see: Nerya et al. (2003 ▶); Dawley et al. (1993 ▶); Maeda et al. (1991 ▶); Lee, et al. (2007 ▶).

Experimental

Crystal data

C16H16O7

M = 320.29

Monoclinic,

a = 11.552 (2) Å

b = 12.817 (3) Å

c = 10.572 (2) Å

β = 105.57 (3)°

V = 1507.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 (2) K

0.2 × 0.2 × 0.16 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

4251 measured reflections

3444 independent reflections

2176 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 400 reflections intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.126

S = 1.01

3444 reflections

219 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062009/lx2033sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062009/lx2033Isup2.hkl

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

C16H16O7	F000 = 672
Mr = 320.29	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.552 (2) Å	θ = 11.4–14.2º
b = 12.817 (3) Å	µ = 0.11 mm−1
c = 10.572 (2) Å	T = 295 (2) K
β = 105.57 (3)º	Block, colorless
V = 1507.9 (6) Å3	0.2 × 0.2 × 0.16 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	θmin = 2.4º
Non–profiled ω/2θ scans	h = 0→14
Absorption correction: none	k = −16→2
4251 measured reflections	l = −13→13
3444 independent reflections	3 standard reflections
2176 reflections with I > 2σ(I)	every 400 reflections
Rint = 0.030	intensity decay: 2%
θmax = 27.5º

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0489P)2 + 0.3432P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.050	(Δ/σ)max < 0.001
wR(F2) = 0.126	Δρmax = 0.23 e Å−3
S = 1.02	Δρmin = −0.20 e Å−3
3444 reflections	Extinction correction: none
219 parameters

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.

	x	y	z	Uiso*/Ueq
O1	−0.00088 (14)	−0.18103 (12)	0.14141 (16)	0.0519 (4)
O2	0.09341 (15)	−0.33144 (11)	0.01850 (15)	0.0509 (4)
O3	0.27941 (14)	−0.29798 (11)	−0.07081 (15)	0.0463 (4)
O4	0.41661 (13)	0.07744 (11)	0.09149 (15)	0.0434 (4)
O5	0.24027 (13)	0.13828 (11)	0.11272 (16)	0.0482 (4)
O6	0.24533 (18)	0.48003 (14)	−0.05695 (17)	0.0619 (5)
H6O	0.261 (3)	0.541 (3)	−0.030 (3)	0.107 (12)*
O7	0.39231 (17)	0.54885 (12)	0.17566 (19)	0.0554 (5)
H7O	0.448 (3)	0.556 (2)	0.244 (3)	0.083 (11)*
C1	0.25245 (18)	−0.04039 (15)	0.07245 (19)	0.0339 (5)
C2	0.15217 (18)	−0.05794 (16)	0.1181 (2)	0.0374 (5)
H2	0.1214	−0.0047	0.1594	0.045*
C3	0.09822 (18)	−0.15538 (17)	0.1017 (2)	0.0384 (5)
C4	0.14486 (19)	−0.23470 (15)	0.0401 (2)	0.0369 (5)
C5	0.24393 (19)	−0.21565 (15)	−0.00864 (19)	0.0348 (5)
C6	0.29865 (18)	−0.11831 (15)	0.0089 (2)	0.0350 (5)
H6	0.3657	−0.1054	−0.0216	0.042*
C7	0.31335 (19)	0.06225 (15)	0.09277 (19)	0.0353 (5)
C8	0.28605 (19)	0.24148 (15)	0.1316 (2)	0.0388 (5)
C9	0.2473 (2)	0.31040 (16)	0.0299 (2)	0.0421 (5)
H9	0.1966	0.2881	−0.0495	0.05*
C10	0.28413 (19)	0.41347 (16)	0.0461 (2)	0.0402 (5)
C11	0.35900 (18)	0.44546 (15)	0.1663 (2)	0.0383 (5)
C12	0.3939 (2)	0.37553 (18)	0.2672 (2)	0.0441 (5)
H12	0.4424	0.3978	0.3478	0.053*
C13	0.3579 (2)	0.27155 (17)	0.2510 (2)	0.0444 (5)
H13	0.382	0.224	0.3194	0.053*
C14	−0.0468 (2)	−0.1053 (2)	0.2138 (2)	0.0520 (6)
H14A	0.0153	−0.0851	0.2901	0.078*
H14B	−0.1131	−0.1346	0.2405	0.078*
H14C	−0.0737	−0.0452	0.1596	0.078*
C15	0.0859 (2)	−0.38926 (18)	0.1315 (3)	0.0591 (7)
H15A	0.1518	−0.3706	0.2048	0.089*
H15B	0.0893	−0.4626	0.1141	0.089*
H15C	0.0115	−0.3735	0.1514	0.089*
C16	0.3815 (2)	−0.28499 (19)	−0.1210 (3)	0.0572 (7)
H16A	0.3659	−0.2304	−0.1855	0.086*
H16B	0.3971	−0.349	−0.1606	0.086*
H16C	0.4502	−0.2668	−0.0505	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0493 (9)	0.0470 (9)	0.0685 (11)	−0.0157 (8)	0.0314 (8)	−0.0152 (8)
O2	0.0682 (11)	0.0364 (8)	0.0530 (9)	−0.0229 (8)	0.0249 (8)	−0.0078 (7)
O3	0.0567 (10)	0.0310 (8)	0.0592 (9)	−0.0067 (7)	0.0293 (8)	−0.0079 (7)
O4	0.0393 (9)	0.0319 (8)	0.0603 (10)	−0.0038 (7)	0.0155 (7)	−0.0008 (7)
O5	0.0411 (8)	0.0249 (7)	0.0802 (12)	−0.0018 (7)	0.0189 (8)	−0.0017 (7)
O6	0.0868 (14)	0.0336 (9)	0.0539 (11)	−0.0055 (9)	−0.0011 (9)	0.0021 (8)
O7	0.0614 (11)	0.0327 (9)	0.0638 (11)	−0.0104 (8)	0.0026 (9)	−0.0078 (8)
C1	0.0359 (11)	0.0267 (10)	0.0374 (11)	−0.0018 (9)	0.0069 (9)	0.0021 (9)
C2	0.0389 (11)	0.0303 (10)	0.0433 (12)	−0.0017 (9)	0.0112 (9)	−0.0036 (9)
C3	0.0375 (11)	0.0394 (12)	0.0395 (12)	−0.0068 (9)	0.0123 (10)	−0.0023 (10)
C4	0.0434 (12)	0.0304 (11)	0.0357 (11)	−0.0090 (9)	0.0086 (9)	−0.0013 (9)
C5	0.0426 (12)	0.0277 (10)	0.0345 (11)	−0.0003 (9)	0.0110 (9)	0.0001 (9)
C6	0.0350 (11)	0.0305 (10)	0.0408 (12)	−0.0022 (9)	0.0124 (9)	0.0043 (9)
C7	0.0381 (12)	0.0283 (10)	0.0379 (11)	−0.0007 (9)	0.0075 (9)	0.0026 (9)
C8	0.0370 (11)	0.0251 (10)	0.0575 (14)	−0.0007 (9)	0.0182 (10)	−0.0037 (10)
C9	0.0418 (12)	0.0322 (11)	0.0489 (13)	−0.0027 (10)	0.0066 (10)	−0.0087 (10)
C10	0.0445 (12)	0.0290 (11)	0.0457 (13)	0.0012 (9)	0.0096 (10)	−0.0008 (10)
C11	0.0381 (11)	0.0278 (10)	0.0494 (13)	−0.0009 (9)	0.0124 (10)	−0.0085 (10)
C12	0.0439 (12)	0.0441 (13)	0.0420 (12)	−0.0013 (10)	0.0074 (10)	−0.0054 (10)
C13	0.0477 (13)	0.0381 (12)	0.0487 (13)	0.0031 (10)	0.0150 (11)	0.0049 (10)
C14	0.0499 (13)	0.0566 (15)	0.0554 (15)	−0.0032 (12)	0.0241 (12)	−0.0083 (12)
C15	0.0704 (17)	0.0391 (13)	0.0760 (18)	−0.0060 (12)	0.0340 (15)	0.0078 (13)
C16	0.0606 (16)	0.0463 (14)	0.0754 (17)	−0.0061 (12)	0.0369 (14)	−0.0136 (13)

O1—C3	1.361 (2)	C5—C6	1.388 (3)
O1—C14	1.424 (3)	C6—H6	0.93
O2—C4	1.367 (2)	C8—C13	1.366 (3)
O2—C15	1.428 (3)	C8—C9	1.371 (3)
O3—C5	1.363 (2)	C9—C10	1.384 (3)
O3—C16	1.427 (3)	C9—H9	0.93
O4—C7	1.212 (2)	C10—C11	1.393 (3)
O5—C7	1.343 (2)	C11—C12	1.369 (3)
O5—C8	1.419 (2)	C12—C13	1.393 (3)
O6—C10	1.362 (3)	C12—H12	0.93
O6—H6O	0.83 (3)	C13—H13	0.93
O7—C11	1.376 (2)	C14—H14A	0.96
O7—H7O	0.84 (3)	C14—H14B	0.96
C1—C2	1.388 (3)	C14—H14C	0.96
C1—C6	1.388 (3)	C15—H15A	0.96
C1—C7	1.480 (3)	C15—H15B	0.96
C2—C3	1.386 (3)	C15—H15C	0.96
C2—H2	0.93	C16—H16A	0.96
C3—C4	1.391 (3)	C16—H16B	0.96
C4—C5	1.397 (3)	C16—H16C	0.96
C3—O1—C14	117.83 (17)	C10—C9—H9	120.2
C4—O2—C15	116.87 (18)	O6—C10—C9	118.3 (2)
C5—O3—C16	118.32 (16)	O6—C10—C11	122.40 (19)
C7—O5—C8	118.20 (16)	C9—C10—C11	119.3 (2)
C10—O6—H6O	109 (2)	C12—C11—O7	123.8 (2)
C11—O7—H7O	108 (2)	C12—C11—C10	119.94 (19)
C2—C1—C6	121.14 (18)	O7—C11—C10	116.3 (2)
C2—C1—C7	120.15 (18)	C11—C12—C13	121.0 (2)
C6—C1—C7	118.70 (18)	C11—C12—H12	119.5
C3—C2—C1	119.46 (19)	C13—C12—H12	119.5
C3—C2—H2	120.3	C8—C13—C12	118.1 (2)
C1—C2—H2	120.3	C8—C13—H13	120.9
O1—C3—C2	124.49 (19)	C12—C13—H13	120.9
O1—C3—C4	115.54 (18)	O1—C14—H14A	109.5
C2—C3—C4	119.97 (19)	O1—C14—H14B	109.5
O2—C4—C3	122.36 (19)	H14A—C14—H14B	109.5
O2—C4—C5	117.33 (19)	O1—C14—H14C	109.5
C3—C4—C5	120.22 (18)	H14A—C14—H14C	109.5
O3—C5—C6	125.10 (18)	H14B—C14—H14C	109.5
O3—C5—C4	115.13 (17)	O2—C15—H15A	109.5
C6—C5—C4	119.77 (18)	O2—C15—H15B	109.5
C1—C6—C5	119.39 (19)	H15A—C15—H15B	109.5
C1—C6—H6	120.3	O2—C15—H15C	109.5
C5—C6—H6	120.3	H15A—C15—H15C	109.5
O4—C7—O5	123.18 (18)	H15B—C15—H15C	109.5
O4—C7—C1	124.89 (19)	O3—C16—H16A	109.5
O5—C7—C1	111.93 (17)	O3—C16—H16B	109.5
C13—C8—C9	122.2 (2)	H16A—C16—H16B	109.5
C13—C8—O5	120.3 (2)	O3—C16—H16C	109.5
C9—C8—O5	117.3 (2)	H16A—C16—H16C	109.5
C8—C9—C10	119.5 (2)	H16B—C16—H16C	109.5
C8—C9—H9	120.2
C6—C1—C2—C3	0.9 (3)	C8—O5—C7—O4	0.8 (3)
C7—C1—C2—C3	−178.15 (18)	C8—O5—C7—C1	−179.03 (18)
C14—O1—C3—C2	−5.1 (3)	C2—C1—C7—O4	158.2 (2)
C14—O1—C3—C4	175.30 (19)	C6—C1—C7—O4	−21.0 (3)
C1—C2—C3—O1	−179.38 (19)	C2—C1—C7—O5	−22.1 (3)
C1—C2—C3—C4	0.2 (3)	C6—C1—C7—O5	158.83 (18)
C15—O2—C4—C3	−60.4 (3)	C7—O5—C8—C13	−79.4 (3)
C15—O2—C4—C5	123.0 (2)	C7—O5—C8—C9	105.9 (2)
O1—C3—C4—O2	1.2 (3)	C13—C8—C9—C10	1.8 (3)
C2—C3—C4—O2	−178.35 (19)	O5—C8—C9—C10	176.44 (19)
O1—C3—C4—C5	177.74 (18)	C8—C9—C10—O6	179.3 (2)
C2—C3—C4—C5	−1.9 (3)	C8—C9—C10—C11	−0.7 (3)
C16—O3—C5—C6	0.8 (3)	O6—C10—C11—C12	179.1 (2)
C16—O3—C5—C4	−178.79 (19)	C9—C10—C11—C12	−0.9 (3)
O2—C4—C5—O3	−1.2 (3)	O6—C10—C11—O7	−0.1 (3)
C3—C4—C5—O3	−177.91 (18)	C9—C10—C11—O7	179.9 (2)
O2—C4—C5—C6	179.11 (19)	O7—C11—C12—C13	−179.4 (2)
C3—C4—C5—C6	2.4 (3)	C10—C11—C12—C13	1.5 (3)
C2—C1—C6—C5	−0.3 (3)	C9—C8—C13—C12	−1.3 (3)
C7—C1—C6—C5	178.76 (18)	O5—C8—C13—C12	−175.74 (19)
O3—C5—C6—C1	179.05 (18)	C11—C12—C13—C8	−0.4 (3)
C4—C5—C6—C1	−1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6O···O3i	0.83 (3)	2.13 (4)	2.882 (2)	150 (3)
O7—H7O···O4ii	0.84 (3)	2.02 (3)	2.855 (3)	179 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6O⋯O3i	0.83 (3)	2.13 (4)	2.882 (2)	150 (3)
O7—H7O⋯O4ii	0.84 (3)	2.02 (3)	2.855 (3)	179 (3)

Symmetry codes: (i) ; (ii) .