3-Benzyl-5,7-dimeth-oxy-chroman-4-ol.

In the crystal structure of the title compound, C(18)H(20)O(4), O-H⋯O hydrogen bonds connect the mol-ecules in parallel layers along the b axis.

Related literature

For analogous structures, see Koch et al. (1994 ▶); Porter et al. (1985 ▶). For the biological activity of naturally ocurring homoisoflavanones that possess a 3-benzyl-substituted chroman ring system, see: Zhang et al. (2008 ▶). For our work on the synthesis and characterization of natural products from this family of compounds in the search for new medical agents, see: Shaikh et al. (2011 ▶).

Experimental

Crystal data

C18H20O4

M = 300.34

Monoclinic,

a = 9.870 (5) Å

b = 11.211 (6) Å

c = 14.603 (7) Å

β = 107.072 (7)°

V = 1544.6 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.37 × 0.24 × 0.20 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

12055 measured reflections

3882 independent reflections

3369 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.04

3882 reflections

203 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002066/pb2047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002066/pb2047Isup2.hkl

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

C18H20O4	1544.6(13)
Mr = 300.34	Dx = 1.292 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.870 (5) Å	Cell parameters from 12055 reflections
b = 11.211 (6) Å	θ = 2.2–28.5°
c = 14.603 (7) Å	µ = 0.09 mm−1
β = 107.072 (7)°	T = 100 K
V = 1544.6 (13) Å3	Needle, colourless
Z = 4	0.37 × 0.24 × 0.20 mm
F(000) = 640

Bruker Kappa DUO APEXII diffractometer	3369 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 28.5°, θmin = 2.2°
0.5° φ scans and ω scans	h = −12→13
12055 measured reflections	k = −15→14
3882 independent reflections	l = −19→9

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.5109P] where P = (Fo2 + 2Fc2)/3
3882 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.38 e Å−3
1 restraint	Δρmin = −0.21 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	−0.00588 (8)	−0.11619 (7)	0.23516 (5)	0.01815 (17)
O2	0.16950 (8)	0.17225 (7)	0.31067 (5)	0.01963 (17)
H2O	0.1135 (16)	0.2376 (12)	0.2790 (11)	0.046 (5)*
O3	−0.32946 (8)	0.01390 (7)	−0.06048 (5)	0.02129 (18)
O4	0.08477 (8)	0.24224 (7)	0.08733 (5)	0.01719 (16)
C1	0.10969 (11)	−0.08620 (10)	0.31876 (7)	0.0177 (2)
H1A	0.1427	−0.1592	0.3569	0.021*
H1B	0.0757	−0.0295	0.3591	0.021*
C2	0.23245 (10)	−0.03074 (9)	0.29118 (7)	0.0150 (2)
H2	0.2580	−0.0855	0.2448	0.018*
C3	0.18241 (10)	0.08729 (9)	0.23985 (7)	0.01346 (19)
H3	0.2548	0.1163	0.2094	0.016*
C4	0.04340 (10)	0.06766 (9)	0.16310 (7)	0.01331 (19)
C5	−0.04198 (10)	−0.03082 (9)	0.16389 (7)	0.0144 (2)
C6	−0.16888 (11)	−0.05346 (9)	0.09140 (7)	0.0165 (2)
H6	−0.2252	−0.1213	0.0942	0.020*
C7	−0.20927 (10)	0.02633 (10)	0.01570 (7)	0.0162 (2)
C8	−0.12787 (11)	0.12749 (9)	0.01173 (7)	0.0163 (2)
H8	−0.1576	0.1821	−0.0400	0.020*
C9	−0.00293 (10)	0.14667 (9)	0.08470 (7)	0.01417 (19)
C10	0.36316 (11)	−0.01853 (10)	0.37985 (7)	0.0185 (2)
H10A	0.3408	0.0374	0.4259	0.022*
H10B	0.3851	−0.0972	0.4116	0.022*
C11	0.49155 (11)	0.02629 (10)	0.35418 (7)	0.0177 (2)
C12	0.58336 (12)	−0.05326 (11)	0.32883 (8)	0.0232 (2)
H12	0.5668	−0.1366	0.3300	0.028*
C13	0.69930 (12)	−0.01154 (14)	0.30172 (9)	0.0313 (3)
H13	0.7614	−0.0666	0.2851	0.038*
C14	0.72403 (13)	0.11021 (14)	0.29902 (9)	0.0343 (3)
H14	0.8024	0.1387	0.2800	0.041*
C15	0.63369 (13)	0.18964 (13)	0.32419 (9)	0.0307 (3)
H15	0.6504	0.2730	0.3225	0.037*
C16	0.51859 (12)	0.14850 (11)	0.35193 (8)	0.0221 (2)
H16	0.4578	0.2040	0.3695	0.027*
C17	−0.40947 (12)	−0.09390 (11)	−0.06520 (8)	0.0237 (2)
H17A	−0.4920	−0.0922	−0.1223	0.036*
H17B	−0.4413	−0.1006	−0.0079	0.036*
H17C	−0.3497	−0.1626	−0.0687	0.036*
C18	0.05036 (12)	0.31979 (10)	0.00542 (8)	0.0204 (2)
H18A	0.1204	0.3841	0.0158	0.031*
H18B	−0.0441	0.3540	−0.0037	0.031*
H18C	0.0512	0.2742	−0.0516	0.031*

	U11	U22	U33	U12	U13	U23
O1	0.0173 (3)	0.0177 (4)	0.0169 (4)	−0.0036 (3)	0.0012 (3)	0.0048 (3)
O2	0.0239 (4)	0.0178 (4)	0.0151 (3)	0.0049 (3)	0.0025 (3)	−0.0040 (3)
O3	0.0182 (4)	0.0241 (4)	0.0173 (4)	−0.0025 (3)	−0.0014 (3)	−0.0001 (3)
O4	0.0204 (4)	0.0153 (4)	0.0148 (3)	−0.0021 (3)	0.0037 (3)	0.0037 (3)
C1	0.0165 (4)	0.0200 (5)	0.0151 (4)	−0.0024 (4)	0.0022 (4)	0.0045 (4)
C2	0.0148 (4)	0.0150 (5)	0.0150 (4)	0.0008 (4)	0.0043 (4)	0.0013 (4)
C3	0.0149 (4)	0.0139 (5)	0.0116 (4)	−0.0004 (3)	0.0039 (3)	−0.0005 (3)
C4	0.0143 (4)	0.0144 (5)	0.0116 (4)	0.0012 (4)	0.0043 (3)	−0.0006 (3)
C5	0.0158 (4)	0.0149 (5)	0.0132 (4)	0.0018 (4)	0.0056 (4)	0.0012 (4)
C6	0.0154 (4)	0.0171 (5)	0.0172 (5)	−0.0016 (4)	0.0053 (4)	−0.0005 (4)
C7	0.0146 (4)	0.0198 (5)	0.0132 (4)	0.0010 (4)	0.0028 (4)	−0.0028 (4)
C8	0.0189 (5)	0.0169 (5)	0.0125 (4)	0.0023 (4)	0.0038 (4)	0.0016 (4)
C9	0.0169 (4)	0.0132 (4)	0.0136 (4)	0.0008 (4)	0.0062 (4)	−0.0006 (4)
C10	0.0165 (5)	0.0206 (5)	0.0169 (5)	0.0002 (4)	0.0025 (4)	0.0045 (4)
C11	0.0146 (4)	0.0221 (5)	0.0133 (4)	−0.0010 (4)	−0.0009 (4)	0.0021 (4)
C12	0.0199 (5)	0.0253 (6)	0.0217 (5)	0.0031 (4)	0.0020 (4)	0.0013 (4)
C13	0.0180 (5)	0.0516 (8)	0.0235 (6)	0.0070 (5)	0.0047 (4)	0.0035 (5)
C14	0.0173 (5)	0.0596 (9)	0.0227 (6)	−0.0095 (6)	0.0006 (4)	0.0103 (6)
C15	0.0269 (6)	0.0346 (7)	0.0238 (6)	−0.0143 (5)	−0.0033 (5)	0.0066 (5)
C16	0.0212 (5)	0.0226 (6)	0.0187 (5)	−0.0031 (4)	−0.0003 (4)	0.0004 (4)
C17	0.0187 (5)	0.0257 (6)	0.0234 (5)	−0.0043 (4)	0.0011 (4)	−0.0040 (4)
C18	0.0269 (5)	0.0175 (5)	0.0169 (5)	−0.0009 (4)	0.0066 (4)	0.0051 (4)

O1—C5	1.3815 (13)	C8—C9	1.3895 (14)
O1—C1	1.4445 (13)	C8—H8	0.9500
O2—C3	1.4389 (13)	C10—C11	1.5091 (15)
O2—H2O	0.952 (9)	C10—H10A	0.9900
O3—C7	1.3746 (13)	C10—H10B	0.9900
O3—C17	1.4342 (15)	C11—C12	1.3966 (16)
O4—C9	1.3708 (13)	C11—C16	1.3981 (17)
O4—C18	1.4365 (13)	C12—C13	1.3967 (18)
C1—C2	1.5176 (15)	C12—H12	0.9500
C1—H1A	0.9900	C13—C14	1.389 (2)
C1—H1B	0.9900	C13—H13	0.9500
C2—C3	1.5296 (15)	C14—C15	1.384 (2)
C2—C10	1.5423 (15)	C14—H14	0.9500
C2—H2	1.0000	C15—C16	1.3919 (17)
C3—C4	1.5113 (14)	C15—H15	0.9500
C3—H3	1.0000	C16—H16	0.9500
C4—C5	1.3911 (15)	C17—H17A	0.9800
C4—C9	1.4131 (14)	C17—H17B	0.9800
C5—C6	1.4053 (15)	C17—H17C	0.9800
C6—C7	1.3864 (15)	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C7—C8	1.4009 (16)	C18—H18C	0.9800
C5—O1—C1	116.13 (8)	O4—C9—C4	114.56 (9)
C3—O2—H2O	108.8 (10)	C8—C9—C4	121.84 (9)
C7—O3—C17	117.16 (9)	C11—C10—C2	112.17 (9)
C9—O4—C18	117.17 (8)	C11—C10—H10A	109.2
O1—C1—C2	111.41 (9)	C2—C10—H10A	109.2
O1—C1—H1A	109.3	C11—C10—H10B	109.2
C2—C1—H1A	109.3	C2—C10—H10B	109.2
O1—C1—H1B	109.3	H10A—C10—H10B	107.9
C2—C1—H1B	109.3	C12—C11—C16	118.44 (11)
H1A—C1—H1B	108.0	C12—C11—C10	120.71 (10)
C1—C2—C3	108.44 (8)	C16—C11—C10	120.81 (10)
C1—C2—C10	110.47 (9)	C11—C12—C13	120.71 (12)
C3—C2—C10	113.88 (9)	C11—C12—H12	119.6
C1—C2—H2	108.0	C13—C12—H12	119.6
C3—C2—H2	108.0	C14—C13—C12	120.16 (12)
C10—C2—H2	108.0	C14—C13—H13	119.9
O2—C3—C4	112.14 (8)	C12—C13—H13	119.9
O2—C3—C2	107.73 (8)	C15—C14—C13	119.50 (12)
C4—C3—C2	109.25 (8)	C15—C14—H14	120.3
O2—C3—H3	109.2	C13—C14—H14	120.3
C4—C3—H3	109.2	C14—C15—C16	120.57 (13)
C2—C3—H3	109.2	C14—C15—H15	119.7
C5—C4—C9	116.84 (9)	C16—C15—H15	119.7
C5—C4—C3	121.98 (9)	C15—C16—C11	120.62 (12)
C9—C4—C3	121.13 (9)	C15—C16—H16	119.7
O1—C5—C4	122.22 (9)	C11—C16—H16	119.7
O1—C5—C6	114.71 (9)	O3—C17—H17A	109.5
C4—C5—C6	123.04 (9)	O3—C17—H17B	109.5
C7—C6—C5	117.91 (10)	H17A—C17—H17B	109.5
C7—C6—H6	121.0	O3—C17—H17C	109.5
C5—C6—H6	121.0	H17A—C17—H17C	109.5
O3—C7—C6	123.90 (10)	H17B—C17—H17C	109.5
O3—C7—C8	114.69 (9)	O4—C18—H18A	109.5
C6—C7—C8	121.41 (9)	O4—C18—H18B	109.5
C9—C8—C7	118.96 (9)	H18A—C18—H18B	109.5
C9—C8—H8	120.5	O4—C18—H18C	109.5
C7—C8—H8	120.5	H18A—C18—H18C	109.5
O4—C9—C8	123.60 (9)	H18B—C18—H18C	109.5
C5—O1—C1—C2	−44.61 (12)	O3—C7—C8—C9	−178.85 (9)
O1—C1—C2—C3	63.83 (11)	C6—C7—C8—C9	1.05 (15)
O1—C1—C2—C10	−170.72 (8)	C18—O4—C9—C8	−5.74 (14)
C1—C2—C3—O2	73.15 (10)	C18—O4—C9—C4	174.43 (8)
C10—C2—C3—O2	−50.27 (11)	C7—C8—C9—O4	179.55 (9)
C1—C2—C3—C4	−48.90 (11)	C7—C8—C9—C4	−0.63 (15)
C10—C2—C3—C4	−172.32 (8)	C5—C4—C9—O4	179.95 (8)
O2—C3—C4—C5	−100.13 (11)	C3—C4—C9—O4	−2.56 (13)
C2—C3—C4—C5	19.23 (12)	C5—C4—C9—C8	0.11 (14)
O2—C3—C4—C9	82.51 (11)	C3—C4—C9—C8	177.60 (9)
C2—C3—C4—C9	−158.13 (9)	C1—C2—C10—C11	175.01 (9)
C1—O1—C5—C4	12.11 (13)	C3—C2—C10—C11	−62.68 (12)
C1—O1—C5—C6	−169.70 (9)	C2—C10—C11—C12	−88.26 (12)
C9—C4—C5—O1	178.06 (9)	C2—C10—C11—C16	89.45 (12)
C3—C4—C5—O1	0.59 (14)	C16—C11—C12—C13	−0.11 (16)
C9—C4—C5—C6	0.02 (14)	C10—C11—C12—C13	177.66 (10)
C3—C4—C5—C6	−177.45 (9)	C11—C12—C13—C14	−0.46 (17)
O1—C5—C6—C7	−177.79 (9)	C12—C13—C14—C15	0.56 (18)
C4—C5—C6—C7	0.38 (15)	C13—C14—C15—C16	−0.10 (18)
C17—O3—C7—C6	−5.93 (14)	C14—C15—C16—C11	−0.48 (17)
C17—O3—C7—C8	173.97 (9)	C12—C11—C16—C15	0.57 (16)
C5—C6—C7—O3	178.97 (9)	C10—C11—C16—C15	−177.19 (10)
C5—C6—C7—C8	−0.92 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1i	0.95 (1)	1.93 (1)	2.8366 (15)	158.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1i	0.95 (1)	1.93 (1)	2.8366 (15)	158 (2)

Symmetry code: (i) .