Methyl 4-(benz-yloxy)-3-meth-oxy-benzo-ate.

In the title compound, C16H16O4, the aromatic rings are almost normal to one another, making a dihedral angle of 85.81 (10)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains propagating along the b-axis direction. There are also C-H⋯π inter-actions present which link the chains, forming two-dimensional networks lying parallel to (102).

Related literature

For details of the anti­cancer properties of the drug Cediranib {systematic name: 4-[(4-fluoro-2-methyl-1H-indol-5-yl)­oxy]-6-meth­oxy-7-[3-(pyrrolidin-1-yl)prop­oxy]quinazol­ine}, for which the title compound is an important inter­mediate in the synthesis, see: Folkman (1996 ▶). For the synthetic procedure, see: Li & Zhang (2012 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16O4

M = 272.29

Monoclinic,

a = 5.2466 (7) Å

b = 17.973 (2) Å

c = 14.8785 (18) Å

β = 94.018 (3)°

V = 1399.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.12 × 0.12 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.989, T max = 0.991

7732 measured reflections

2454 independent reflections

1666 reflections with I > 2σ(I)

R int = 0.029

3 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.138

S = 0.91

2454 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

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.

Crystal structure: contains datablock(s) I, wang. DOI: 10.1107/S1600536813025415/su2645sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025415/su2645Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025415/su2645Isup3.cml

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

C16H16O4	F(000) = 576
Mr = 272.29	Dx = 1.292 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1683 reflections
a = 5.2466 (7) Å	θ = 5.3–45.5°
b = 17.973 (2) Å	µ = 0.09 mm−1
c = 14.8785 (18) Å	T = 293 K
β = 94.018 (3)°	Block, colourless
V = 1399.6 (3) Å3	0.12 × 0.12 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1666 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
ω/2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = −21→14
Tmin = 0.989, Tmax = 0.991	l = −16→17
7732 measured reflections	3 standard reflections every 120 min
2454 independent reflections	intensity decay: 1%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0874P)2 + 0.101P] where P = (Fo2 + 2Fc2)/3
2454 reflections	(Δ/σ)max = 0.005
182 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 e Å−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
O1	0.8880 (3)	0.30300 (7)	0.59482 (9)	0.0538 (4)
O2	0.5720 (3)	0.29367 (7)	0.71794 (9)	0.0573 (4)
O3	0.3782 (4)	0.61921 (8)	0.64985 (12)	0.0841 (5)
O4	0.2344 (3)	0.55257 (8)	0.76146 (10)	0.0702 (5)
C1	1.3108 (4)	0.18726 (11)	0.53747 (14)	0.0585 (6)
H1	1.4248	0.2124	0.5774	0.070*
C2	1.3529 (5)	0.11390 (13)	0.51813 (17)	0.0714 (7)
H2	1.4940	0.0896	0.5457	0.086*
C3	1.1895 (5)	0.07597 (12)	0.45856 (17)	0.0703 (7)
H3	1.2194	0.0263	0.4453	0.084*
C4	0.9838 (5)	0.11185 (14)	0.41926 (18)	0.0789 (7)
H4	0.8709	0.0866	0.3790	0.095*
C5	0.9409 (4)	0.18540 (14)	0.43850 (16)	0.0682 (6)
H5	0.8002	0.2095	0.4104	0.082*
C6	1.1025 (4)	0.22385 (11)	0.49856 (13)	0.0475 (5)
C7	1.0484 (4)	0.30341 (11)	0.52037 (14)	0.0552 (5)
H7A	1.2064	0.3297	0.5366	0.066*
H7B	0.9622	0.3279	0.4687	0.066*
C8	0.7756 (3)	0.36807 (10)	0.61691 (12)	0.0456 (5)
C9	0.6001 (3)	0.36283 (10)	0.68347 (12)	0.0430 (4)
C10	0.4714 (3)	0.42556 (10)	0.70828 (12)	0.0463 (5)
H10	0.3552	0.4222	0.7525	0.056*
C11	0.5133 (4)	0.49364 (10)	0.66796 (12)	0.0481 (5)
C12	0.6864 (4)	0.49822 (11)	0.60332 (15)	0.0629 (6)
H12	0.7146	0.5438	0.5760	0.075*
C13	0.8196 (4)	0.43625 (11)	0.57813 (16)	0.0631 (6)
H13	0.9389	0.4404	0.5350	0.076*
C14	0.3712 (4)	0.28318 (11)	0.77630 (14)	0.0581 (6)
H14A	0.3996	0.3146	0.8282	0.087*
H14B	0.3679	0.2321	0.7951	0.087*
H14C	0.2109	0.2958	0.7450	0.087*
C15	0.3720 (4)	0.56143 (11)	0.69069 (15)	0.0561 (5)
C16	0.0836 (5)	0.61549 (13)	0.78568 (19)	0.0836 (8)
H16A	0.1948	0.6546	0.8085	0.100*
H16B	−0.0272	0.6009	0.8312	0.100*
H16C	−0.0171	0.6329	0.7335	0.100*

	U11	U22	U33	U12	U13	U23
O1	0.0645 (9)	0.0414 (7)	0.0585 (8)	0.0127 (6)	0.0255 (7)	0.0029 (6)
O2	0.0783 (10)	0.0372 (7)	0.0597 (8)	0.0080 (6)	0.0284 (7)	0.0058 (6)
O3	0.1240 (15)	0.0404 (9)	0.0900 (12)	0.0199 (8)	0.0231 (10)	0.0051 (8)
O4	0.0835 (11)	0.0497 (9)	0.0804 (10)	0.0211 (7)	0.0277 (9)	−0.0038 (7)
C1	0.0590 (13)	0.0555 (13)	0.0617 (13)	0.0077 (10)	0.0084 (10)	−0.0034 (10)
C2	0.0729 (15)	0.0581 (14)	0.0848 (17)	0.0183 (12)	0.0168 (13)	0.0063 (13)
C3	0.0827 (17)	0.0462 (12)	0.0868 (17)	−0.0010 (12)	0.0399 (14)	−0.0076 (12)
C4	0.0712 (16)	0.0758 (18)	0.0911 (18)	−0.0194 (13)	0.0155 (14)	−0.0256 (14)
C5	0.0511 (12)	0.0743 (16)	0.0796 (16)	0.0061 (11)	0.0058 (11)	−0.0059 (13)
C6	0.0469 (11)	0.0491 (11)	0.0487 (11)	0.0023 (9)	0.0188 (9)	0.0002 (9)
C7	0.0582 (12)	0.0511 (12)	0.0591 (12)	0.0094 (9)	0.0242 (10)	0.0056 (10)
C8	0.0485 (10)	0.0385 (10)	0.0504 (10)	0.0063 (8)	0.0082 (8)	−0.0017 (8)
C9	0.0503 (10)	0.0344 (9)	0.0448 (10)	0.0026 (8)	0.0062 (8)	0.0007 (8)
C10	0.0510 (11)	0.0433 (11)	0.0456 (10)	0.0046 (8)	0.0097 (8)	−0.0038 (9)
C11	0.0548 (11)	0.0358 (10)	0.0538 (11)	0.0039 (8)	0.0054 (9)	−0.0034 (9)
C12	0.0768 (14)	0.0374 (10)	0.0771 (15)	0.0008 (10)	0.0244 (12)	0.0060 (10)
C13	0.0676 (13)	0.0468 (12)	0.0786 (14)	0.0061 (10)	0.0323 (11)	0.0080 (11)
C14	0.0702 (14)	0.0482 (12)	0.0581 (12)	−0.0017 (10)	0.0208 (10)	0.0073 (10)
C15	0.0660 (13)	0.0408 (11)	0.0613 (13)	0.0066 (9)	0.0027 (11)	−0.0086 (10)
C16	0.0882 (18)	0.0625 (15)	0.1027 (19)	0.0262 (13)	0.0258 (15)	−0.0171 (14)

O1—C8	1.360 (2)	C7—H7A	0.9700
O1—C7	1.437 (2)	C7—H7B	0.9700
O2—C9	1.357 (2)	C8—C13	1.381 (3)
O2—C14	1.424 (2)	C8—C9	1.402 (3)
O3—C15	1.205 (2)	C9—C10	1.378 (2)
O4—C15	1.327 (3)	C10—C11	1.387 (3)
O4—C16	1.440 (2)	C10—H10	0.9300
C1—C6	1.369 (3)	C11—C12	1.371 (3)
C1—C2	1.371 (3)	C11—C15	1.477 (3)
C1—H1	0.9300	C12—C13	1.381 (3)
C2—C3	1.371 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.354 (3)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.374 (3)	C14—H14C	0.9600
C4—H4	0.9300	C16—H16A	0.9601
C5—C6	1.374 (3)	C16—H16B	0.9601
C5—H5	0.9300	C16—H16C	0.9600
C6—C7	1.498 (3)
C8—O1—C7	117.96 (14)	O2—C9—C10	125.47 (16)
C9—O2—C14	117.16 (14)	O2—C9—C8	115.00 (15)
C15—O4—C16	116.30 (17)	C10—C9—C8	119.53 (16)
C6—C1—C2	120.6 (2)	C9—C10—C11	120.70 (17)
C6—C1—H1	119.7	C9—C10—H10	119.7
C2—C1—H1	119.7	C11—C10—H10	119.7
C1—C2—C3	120.8 (2)	C12—C11—C10	119.29 (17)
C1—C2—H2	119.6	C12—C11—C15	118.61 (17)
C3—C2—H2	119.6	C10—C11—C15	122.08 (18)
C4—C3—C2	119.1 (2)	C11—C12—C13	120.99 (18)
C4—C3—H3	120.5	C11—C12—H12	119.5
C2—C3—H3	120.5	C13—C12—H12	119.5
C3—C4—C5	120.3 (2)	C12—C13—C8	120.00 (19)
C3—C4—H4	119.8	C12—C13—H13	120.0
C5—C4—H4	119.8	C8—C13—H13	120.0
C4—C5—C6	121.1 (2)	O2—C14—H14A	109.5
C4—C5—H5	119.4	O2—C14—H14B	109.5
C6—C5—H5	119.4	H14A—C14—H14B	109.5
C1—C6—C5	118.12 (19)	O2—C14—H14C	109.5
C1—C6—C7	121.67 (18)	H14A—C14—H14C	109.5
C5—C6—C7	120.21 (18)	H14B—C14—H14C	109.5
O1—C7—C6	106.99 (15)	O3—C15—O4	122.60 (18)
O1—C7—H7A	110.3	O3—C15—C11	124.3 (2)
C6—C7—H7A	110.3	O4—C15—C11	113.09 (18)
O1—C7—H7B	110.3	O4—C16—H16A	109.5
C6—C7—H7B	110.3	O4—C16—H16B	109.4
H7A—C7—H7B	108.6	H16A—C16—H16B	109.5
O1—C8—C13	125.04 (17)	O4—C16—H16C	109.5
O1—C8—C9	115.48 (15)	H16A—C16—H16C	109.5
C13—C8—C9	119.47 (16)	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.9 (3)	O1—C8—C9—C10	−178.12 (16)
C1—C2—C3—C4	−0.5 (3)	C13—C8—C9—C10	0.9 (3)
C2—C3—C4—C5	0.4 (4)	O2—C9—C10—C11	−179.44 (17)
C3—C4—C5—C6	−0.9 (4)	C8—C9—C10—C11	0.2 (3)
C2—C1—C6—C5	−1.3 (3)	C9—C10—C11—C12	−0.5 (3)
C2—C1—C6—C7	178.4 (2)	C9—C10—C11—C15	177.82 (18)
C4—C5—C6—C1	1.3 (3)	C10—C11—C12—C13	−0.2 (3)
C4—C5—C6—C7	−178.4 (2)	C15—C11—C12—C13	−178.6 (2)
C8—O1—C7—C6	−168.61 (16)	C11—C12—C13—C8	1.3 (4)
C1—C6—C7—O1	−90.8 (2)	O1—C8—C13—C12	177.3 (2)
C5—C6—C7—O1	88.9 (2)	C9—C8—C13—C12	−1.6 (3)
C7—O1—C8—C13	−5.6 (3)	C16—O4—C15—O3	2.0 (3)
C7—O1—C8—C9	173.40 (16)	C16—O4—C15—C11	−177.77 (18)
C14—O2—C9—C10	8.2 (3)	C12—C11—C15—O3	8.1 (3)
C14—O2—C9—C8	−171.46 (16)	C10—C11—C15—O3	−170.3 (2)
O1—C8—C9—O2	1.5 (2)	C12—C11—C15—O4	−172.12 (18)
C13—C8—C9—O2	−179.44 (18)	C10—C11—C15—O4	9.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O3i	0.96	2.53	3.379 (3)	147
C14—H14A···Cgii	0.96	2.75	3.519 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O3i	0.96	2.53	3.379 (3)	147
C14—H14A⋯Cg ii	0.96	2.75	3.519 (2)	137

Symmetry codes: (i) ; (ii) .