2'-Carb-oxy-meth-oxy-4,4'-bis-(3-methyl-but-2-en-yloxy)chalcone.

In the title compound, C(27)H(30)O(6), also known as sofalcone, an anti-ulcer agent used for the protection of gastric mucosa-, the two benzene rings form a dihedral angle of 6.78 (11)°. Inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers, which are further linked by weak C-H⋯O inter-actions into ribbons propagated in [2[Formula: see text]0]. Finally, π-π inter-actions between the benzene rings [centroid-centroid distance = 3.583 (13) Å] stabilize the crystal packing.

Related literature

For background to the bioactivity and applications of the title compound, see: Tanaka et al. (2009 ▶). For a related structure, see: Cheng et al. (2007 ▶). For the preparation of the title compound, see: Kyogoku et al. (1978 ▶, 1979 ▶); Liu et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C27H30O6

M = 450.51

Triclinic,

a = 7.4496 (15) Å

b = 12.195 (2) Å

c = 13.085 (3) Å

α = 88.39 (3)°

β = 78.53 (3)°

γ = 86.99 (3)°

V = 1163.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.12 × 0.10 × 0.08 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.989, T max = 0.993

11767 measured reflections

4097 independent reflections

2371 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.116

S = 0.92

4097 reflections

303 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablocks global, I. DOI: 10.1107/S1600536811008300/cv5057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008300/cv5057Isup2.hkl

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

C27H30O6	Z = 2
Mr = 450.51	F(000) = 480
Triclinic, P1	Dx = 1.286 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4496 (15) Å	Cell parameters from 3474 reflections
b = 12.195 (2) Å	θ = 2.3–27.9°
c = 13.085 (3) Å	µ = 0.09 mm−1
α = 88.39 (3)°	T = 113 K
β = 78.53 (3)°	Prism, yellow
γ = 86.99 (3)°	0.12 × 0.10 × 0.08 mm
V = 1163.3 (4) Å3

Rigaku Saturn diffractometer	4097 independent reflections
Radiation source: rotating anode	2371 reflections with I > 2σ(I)
confocal	Rint = 0.078
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −8→8
Tmin = 0.989, Tmax = 0.993	k = −14→14
11767 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0421P)2] where P = (Fo2 + 2Fc2)/3
4097 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 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	0.45375 (16)	−0.07058 (11)	1.21292 (10)	0.0295 (4)
O2	0.39551 (15)	0.25262 (10)	1.01329 (10)	0.0245 (3)
O3	0.19896 (16)	0.42849 (11)	0.96442 (10)	0.0275 (4)
O4	−0.04272 (16)	0.38360 (11)	1.08729 (10)	0.0281 (4)
H4	−0.0869	0.4422	1.0692	0.042*
O5	0.96148 (17)	0.22153 (11)	0.88715 (11)	0.0325 (4)
O6	0.52436 (16)	0.79502 (10)	0.64049 (10)	0.0290 (4)
C1	0.6943 (2)	0.16654 (15)	1.00089 (14)	0.0206 (4)
C2	0.7978 (2)	0.07896 (15)	1.03331 (15)	0.0232 (5)
H2	0.9231	0.0750	1.0059	0.028*
C3	0.7285 (2)	−0.00236 (16)	1.10304 (14)	0.0239 (5)
H3	0.8045	−0.0591	1.1219	0.029*
C4	0.5426 (2)	0.00300 (15)	1.14398 (14)	0.0225 (5)
C5	0.4324 (2)	0.08869 (15)	1.11472 (14)	0.0228 (5)
H5	0.3075	0.0921	1.1429	0.027*
C6	0.5055 (2)	0.16926 (15)	1.04415 (14)	0.0214 (5)
C7	0.5612 (3)	−0.16271 (16)	1.24391 (16)	0.0302 (5)
H7A	0.6645	−0.1375	1.2701	0.036*
H7B	0.6075	−0.2098	1.1850	0.036*
C8	0.4368 (3)	−0.22398 (16)	1.32763 (15)	0.0285 (5)
H8	0.3166	−0.1963	1.3476	0.034*
C9	0.4851 (3)	−0.31441 (16)	1.37529 (15)	0.0291 (5)
C10	0.6741 (3)	−0.36753 (17)	1.35051 (17)	0.0428 (6)
H10A	0.7473	−0.3280	1.2941	0.064*
H10B	0.6672	−0.4421	1.3306	0.064*
H10C	0.7290	−0.3665	1.4109	0.064*
C11	0.3521 (3)	−0.37149 (18)	1.45850 (16)	0.0434 (6)
H11A	0.2355	−0.3316	1.4694	0.065*
H11B	0.3977	−0.3747	1.5222	0.065*
H11C	0.3381	−0.4447	1.4371	0.065*
C12	0.2107 (2)	0.26291 (15)	1.06756 (15)	0.0234 (5)
H12A	0.2065	0.2641	1.1421	0.028*
H12B	0.1442	0.2008	1.0530	0.028*
C13	0.1247 (2)	0.36717 (15)	1.03284 (15)	0.0223 (5)
C14	0.7976 (2)	0.24378 (15)	0.92286 (15)	0.0222 (5)
C15	0.7105 (3)	0.34591 (15)	0.88957 (15)	0.0250 (5)
H15	0.5896	0.3648	0.9202	0.030*
C16	0.8002 (3)	0.41176 (15)	0.81682 (15)	0.0246 (5)
H16	0.9221	0.3914	0.7899	0.030*
C17	0.7269 (3)	0.51316 (15)	0.77462 (15)	0.0238 (5)
C18	0.5463 (2)	0.55068 (15)	0.80792 (15)	0.0265 (5)
H18	0.4715	0.5119	0.8605	0.032*
C19	0.4741 (3)	0.64361 (16)	0.76561 (15)	0.0263 (5)
H19	0.3522	0.6665	0.7893	0.032*
C20	0.5842 (3)	0.70289 (15)	0.68747 (15)	0.0237 (5)
C21	0.7656 (3)	0.66794 (16)	0.65364 (15)	0.0267 (5)
H21	0.8406	0.7075	0.6017	0.032*
C22	0.8355 (3)	0.57460 (16)	0.69672 (15)	0.0274 (5)
H22	0.9577	0.5521	0.6733	0.033*
C23	0.3328 (2)	0.82802 (16)	0.67028 (15)	0.0291 (5)
H23A	0.3008	0.8407	0.7447	0.035*
H23B	0.2576	0.7710	0.6537	0.035*
C24	0.3013 (3)	0.93145 (17)	0.61086 (16)	0.0361 (6)
H24	0.3969	0.9533	0.5583	0.043*
C25	0.1492 (3)	0.99420 (16)	0.62685 (15)	0.0293 (5)
C26	0.1281 (3)	1.09886 (17)	0.56591 (17)	0.0453 (7)
H26A	0.2386	1.1096	0.5155	0.068*
H26B	0.1048	1.1596	0.6126	0.068*
H26C	0.0273	1.0942	0.5308	0.068*
C27	−0.0158 (3)	0.96821 (18)	0.70712 (16)	0.0382 (6)
H27A	0.0093	0.9020	0.7442	0.057*
H27B	−0.1173	0.9584	0.6737	0.057*
H27C	−0.0457	1.0276	0.7552	0.057*

	U11	U22	U33	U12	U13	U23
O1	0.0232 (7)	0.0239 (8)	0.0385 (9)	0.0037 (6)	−0.0028 (6)	0.0157 (7)
O2	0.0173 (7)	0.0230 (8)	0.0315 (8)	0.0048 (6)	−0.0031 (6)	0.0071 (6)
O3	0.0187 (7)	0.0253 (8)	0.0359 (8)	0.0027 (6)	−0.0011 (6)	0.0096 (7)
O4	0.0198 (8)	0.0236 (9)	0.0375 (9)	0.0061 (6)	−0.0010 (6)	0.0096 (7)
O5	0.0204 (8)	0.0287 (9)	0.0441 (9)	0.0042 (7)	0.0007 (7)	0.0110 (7)
O6	0.0252 (8)	0.0252 (8)	0.0331 (8)	0.0073 (6)	−0.0015 (6)	0.0106 (6)
C1	0.0188 (10)	0.0176 (11)	0.0252 (11)	0.0017 (8)	−0.0048 (8)	0.0007 (9)
C2	0.0160 (10)	0.0222 (12)	0.0310 (12)	0.0007 (9)	−0.0045 (9)	0.0023 (9)
C3	0.0254 (11)	0.0167 (11)	0.0299 (12)	0.0042 (9)	−0.0086 (9)	0.0053 (9)
C4	0.0251 (11)	0.0180 (11)	0.0242 (11)	−0.0012 (9)	−0.0051 (9)	0.0046 (9)
C5	0.0186 (10)	0.0224 (12)	0.0267 (11)	0.0023 (9)	−0.0045 (8)	0.0034 (9)
C6	0.0233 (11)	0.0168 (11)	0.0251 (11)	0.0044 (9)	−0.0089 (9)	0.0011 (9)
C7	0.0318 (12)	0.0213 (12)	0.0367 (13)	0.0062 (9)	−0.0081 (10)	0.0077 (10)
C8	0.0327 (12)	0.0244 (13)	0.0274 (12)	−0.0007 (10)	−0.0041 (9)	0.0008 (10)
C9	0.0424 (13)	0.0218 (12)	0.0242 (11)	−0.0040 (10)	−0.0089 (10)	0.0018 (9)
C10	0.0554 (15)	0.0256 (14)	0.0482 (15)	0.0045 (11)	−0.0152 (12)	0.0100 (11)
C11	0.0607 (16)	0.0346 (15)	0.0361 (13)	−0.0087 (12)	−0.0123 (12)	0.0117 (11)
C12	0.0157 (10)	0.0236 (12)	0.0295 (11)	0.0020 (9)	−0.0024 (8)	0.0024 (9)
C13	0.0166 (11)	0.0220 (12)	0.0285 (11)	0.0006 (9)	−0.0055 (9)	0.0012 (9)
C14	0.0221 (11)	0.0182 (11)	0.0264 (11)	0.0005 (9)	−0.0059 (9)	0.0014 (9)
C15	0.0215 (11)	0.0206 (12)	0.0319 (12)	0.0015 (9)	−0.0042 (9)	0.0044 (9)
C16	0.0216 (11)	0.0211 (12)	0.0300 (12)	0.0025 (9)	−0.0036 (9)	0.0023 (9)
C17	0.0260 (11)	0.0196 (12)	0.0256 (11)	0.0007 (9)	−0.0054 (9)	0.0020 (9)
C18	0.0253 (11)	0.0220 (12)	0.0304 (12)	0.0001 (9)	−0.0032 (9)	0.0081 (9)
C19	0.0217 (11)	0.0237 (12)	0.0316 (12)	0.0019 (9)	−0.0023 (9)	0.0045 (9)
C20	0.0288 (11)	0.0182 (11)	0.0242 (11)	0.0019 (9)	−0.0062 (9)	0.0021 (9)
C21	0.0276 (11)	0.0243 (12)	0.0264 (11)	0.0000 (9)	−0.0023 (9)	0.0056 (9)
C22	0.0221 (11)	0.0256 (12)	0.0322 (12)	0.0030 (9)	−0.0016 (9)	0.0029 (10)
C23	0.0243 (11)	0.0261 (12)	0.0334 (12)	0.0071 (9)	0.0000 (9)	0.0065 (10)
C24	0.0302 (12)	0.0335 (14)	0.0387 (13)	0.0049 (11)	0.0032 (10)	0.0158 (11)
C25	0.0268 (12)	0.0255 (12)	0.0344 (12)	0.0021 (9)	−0.0048 (9)	0.0081 (10)
C26	0.0361 (13)	0.0385 (15)	0.0585 (16)	0.0036 (11)	−0.0067 (12)	0.0212 (12)
C27	0.0306 (12)	0.0448 (15)	0.0375 (13)	0.0069 (11)	−0.0061 (10)	0.0074 (11)

O1—C4	1.355 (2)	C11—H11C	0.9600
O1—C7	1.441 (2)	C12—C13	1.494 (2)
O2—C6	1.374 (2)	C12—H12A	0.9700
O2—C12	1.419 (2)	C12—H12B	0.9700
O3—C13	1.215 (2)	C14—C15	1.469 (3)
O4—C13	1.316 (2)	C15—C16	1.326 (3)
O4—H4	0.8200	C15—H15	0.9300
O5—C14	1.236 (2)	C16—C17	1.464 (3)
O6—C20	1.362 (2)	C16—H16	0.9300
O6—C23	1.442 (2)	C17—C18	1.387 (2)
C1—C2	1.391 (2)	C17—C22	1.396 (3)
C1—C6	1.407 (2)	C18—C19	1.378 (3)
C1—C14	1.494 (3)	C18—H18	0.9300
C2—C3	1.378 (3)	C19—C20	1.389 (3)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.381 (2)	C20—C21	1.384 (3)
C3—H3	0.9300	C21—C22	1.380 (3)
C4—C5	1.387 (2)	C21—H21	0.9300
C5—C6	1.385 (2)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.496 (3)
C7—C8	1.497 (3)	C23—H23A	0.9700
C7—H7A	0.9700	C23—H23B	0.9700
C7—H7B	0.9700	C24—C25	1.318 (3)
C8—C9	1.320 (3)	C24—H24	0.9300
C8—H8	0.9300	C25—C27	1.491 (3)
C9—C10	1.497 (3)	C25—C26	1.504 (3)
C9—C11	1.501 (3)	C26—H26A	0.9600
C10—H10A	0.9600	C26—H26B	0.9600
C10—H10B	0.9600	C26—H26C	0.9600
C10—H10C	0.9600	C27—H27A	0.9600
C11—H11A	0.9600	C27—H27B	0.9600
C11—H11B	0.9600	C27—H27C	0.9600
C4—O1—C7	117.34 (14)	O3—C13—C12	124.87 (17)
C6—O2—C12	117.60 (15)	O4—C13—C12	110.40 (16)
C13—O4—H4	109.5	O5—C14—C15	119.55 (17)
C20—O6—C23	117.28 (14)	O5—C14—C1	118.69 (17)
C2—C1—C6	115.70 (17)	C15—C14—C1	121.75 (16)
C2—C1—C14	115.69 (16)	C16—C15—C14	121.55 (17)
C6—C1—C14	128.60 (17)	C16—C15—H15	119.2
C3—C2—C1	124.82 (18)	C14—C15—H15	119.2
C3—C2—H2	117.6	C15—C16—C17	126.66 (18)
C1—C2—H2	117.6	C15—C16—H16	116.7
C2—C3—C4	117.89 (18)	C17—C16—H16	116.7
C2—C3—H3	121.1	C18—C17—C22	117.20 (18)
C4—C3—H3	121.1	C18—C17—C16	121.73 (17)
O1—C4—C3	125.01 (17)	C22—C17—C16	121.05 (17)
O1—C4—C5	115.13 (16)	C19—C18—C17	122.12 (18)
C3—C4—C5	119.87 (18)	C19—C18—H18	118.9
C6—C5—C4	121.10 (17)	C17—C18—H18	118.9
C6—C5—H5	119.4	C18—C19—C20	119.68 (18)
C4—C5—H5	119.4	C18—C19—H19	120.2
O2—C6—C5	121.04 (16)	C20—C19—H19	120.2
O2—C6—C1	118.32 (17)	O6—C20—C21	116.85 (17)
C5—C6—C1	120.63 (17)	O6—C20—C19	123.79 (17)
O1—C7—C8	106.76 (15)	C21—C20—C19	119.37 (18)
O1—C7—H7A	110.4	C22—C21—C20	120.17 (18)
C8—C7—H7A	110.4	C22—C21—H21	119.9
O1—C7—H7B	110.4	C20—C21—H21	119.9
C8—C7—H7B	110.4	C21—C22—C17	121.45 (18)
H7A—C7—H7B	108.6	C21—C22—H22	119.3
C9—C8—C7	124.88 (19)	C17—C22—H22	119.3
C9—C8—H8	117.6	O6—C23—C24	107.45 (15)
C7—C8—H8	117.6	O6—C23—H23A	110.2
C8—C9—C10	122.93 (19)	C24—C23—H23A	110.2
C8—C9—C11	121.79 (19)	O6—C23—H23B	110.2
C10—C9—C11	115.28 (18)	C24—C23—H23B	110.2
C9—C10—H10A	109.5	H23A—C23—H23B	108.5
C9—C10—H10B	109.5	C25—C24—C23	125.31 (18)
H10A—C10—H10B	109.5	C25—C24—H24	117.3
C9—C10—H10C	109.5	C23—C24—H24	117.3
H10A—C10—H10C	109.5	C24—C25—C27	123.09 (19)
H10B—C10—H10C	109.5	C24—C25—C26	122.65 (19)
C9—C11—H11A	109.5	C27—C25—C26	114.26 (17)
C9—C11—H11B	109.5	C25—C26—H26A	109.5
H11A—C11—H11B	109.5	C25—C26—H26B	109.5
C9—C11—H11C	109.5	H26A—C26—H26B	109.5
H11A—C11—H11C	109.5	C25—C26—H26C	109.5
H11B—C11—H11C	109.5	H26A—C26—H26C	109.5
O2—C12—C13	108.73 (15)	H26B—C26—H26C	109.5
O2—C12—H12A	109.9	C25—C27—H27A	109.5
C13—C12—H12A	109.9	C25—C27—H27B	109.5
O2—C12—H12B	109.9	H27A—C27—H27B	109.5
C13—C12—H12B	109.9	C25—C27—H27C	109.5
H12A—C12—H12B	108.3	H27A—C27—H27C	109.5
O3—C13—O4	124.73 (17)	H27B—C27—H27C	109.5
C6—C1—C2—C3	−0.1 (3)	C6—C1—C14—O5	−173.38 (18)
C14—C1—C2—C3	−178.72 (18)	C2—C1—C14—C15	−173.64 (17)
C1—C2—C3—C4	0.0 (3)	C6—C1—C14—C15	7.9 (3)
C7—O1—C4—C3	−1.5 (3)	O5—C14—C15—C16	4.4 (3)
C7—O1—C4—C5	178.51 (17)	C1—C14—C15—C16	−176.88 (19)
C2—C3—C4—O1	179.78 (18)	C14—C15—C16—C17	177.71 (18)
C2—C3—C4—C5	−0.2 (3)	C15—C16—C17—C18	−0.9 (3)
O1—C4—C5—C6	−179.55 (17)	C15—C16—C17—C22	−179.1 (2)
C3—C4—C5—C6	0.5 (3)	C22—C17—C18—C19	1.0 (3)
C12—O2—C6—C5	9.4 (2)	C16—C17—C18—C19	−177.29 (18)
C12—O2—C6—C1	−171.72 (16)	C17—C18—C19—C20	−0.4 (3)
C4—C5—C6—O2	178.39 (17)	C23—O6—C20—C21	176.04 (16)
C4—C5—C6—C1	−0.5 (3)	C23—O6—C20—C19	−3.7 (3)
C2—C1—C6—O2	−178.62 (16)	C18—C19—C20—O6	179.39 (18)
C14—C1—C6—O2	−0.2 (3)	C18—C19—C20—C21	−0.4 (3)
C2—C1—C6—C5	0.3 (3)	O6—C20—C21—C22	−179.27 (17)
C14—C1—C6—C5	178.73 (19)	C19—C20—C21—C22	0.5 (3)
C4—O1—C7—C8	174.14 (16)	C20—C21—C22—C17	0.1 (3)
O1—C7—C8—C9	179.36 (18)	C18—C17—C22—C21	−0.8 (3)
C7—C8—C9—C10	−0.1 (3)	C16—C17—C22—C21	177.45 (18)
C7—C8—C9—C11	−179.8 (2)	C20—O6—C23—C24	178.69 (16)
C6—O2—C12—C13	171.66 (15)	O6—C23—C24—C25	−170.7 (2)
O2—C12—C13—O3	4.4 (3)	C23—C24—C25—C27	−1.1 (3)
O2—C12—C13—O4	−175.26 (14)	C23—C24—C25—C26	178.5 (2)
C2—C1—C14—O5	5.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.82	1.83	2.6474 (19)	176
C3—H3···O5ii	0.93	2.56	3.456 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.82	1.83	2.6474 (19)	176
C3—H3⋯O5ii	0.93	2.56	3.456 (2)	162

Symmetry codes: (i) ; (ii) .