(Z)-2,3-Bis(3,4-di­methoxy­phenyl)-2-propen-1-ol

In the crystal structure of the title compound, C₁₉H₂₂O₅, intermolecular hydrogen bonding gives rise to centrosymmetric dimers. The conformations of the title compound and its benzene solvate are compared.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.107
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.98 Deg.

Alert level C
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT156_ALERT_4_C Axial System Input Cell not Standard ...........          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.26 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C19 H22 O5

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: TEXRAY (Molecular Structure Corporation, 1985); cell refinement: TEXRAY; data reduction: TEXRAY; program(s) used to solve structure: MITHRIL (Gilmore, 1984); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXTL.

(Z)-2,3-bis(3,4-dimethoxyphenyl)-2-propen-1-ol

Crystal data

C19H22O5	Z = 2
Mr = 330.37	F(000) = 352
Triclinic, P1	Dx = 1.288 Mg m^−3
Hall symbol: -P 1	Melting point = 403–404 K
a = 10.097 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 10.358 (2) Å	Cell parameters from 25 reflections
c = 8.665 (2) Å	θ = 7.0–22.9°
α = 103.08 (2)°	µ = 0.09 mm^−1
β = 101.93 (2)°	T = 295 K
γ = 78.10 (2)°	Prism, colourless
V = 851.5 (3) Å^3	0.34 × 0.23 × 0.18 mm

Data collection

Rigaku AFC6 diffractometer	Rint = 0.025
Radiation source: normal-focus rotating anode	θmax = 25.0°, θmin = 2.1°
Graphite monochromator	h = 0→11
2θ–ω scans	k = −12→12
3180 measured reflections	l = −10→10
2993 independent reflections	3 standard reflections every 150 reflections
1665 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0356P)^2 + 0.1258P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2993 reflections	Δρmax = 0.16 e Å^−3
245 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (3)

Special details

Experimental. Data were collected at room temperature using a Rigaku AFC6R diffractometer. The data were collected using 2θ-ω-scan. Scans of (1.26 + 0.30tanθ) were made at a speed of 4.0ο/min in ω. The weak reflections (I<10.0σ_I) were rescanned (maximum 3 rescans) and the counts were accumulated to assure good counting statistics. Stationary bacground counts were recored on each side of the reflection·The ratio of peak counting time to backgroud counting time was 2:1. The crystal–to–detector distance was 400 mm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9087 (2)	−0.4994 (2)	0.7537 (2)	0.0353 (5)
C2	0.8311 (2)	−0.5249 (2)	0.8571 (2)	0.0373 (5)
H2	0.7539	−0.4633	0.8823	0.038 (6)*
C3	0.8674 (2)	−0.6397 (2)	0.9222 (2)	0.0365 (5)
C4	0.9853 (2)	−0.7318 (2)	0.8870 (2)	0.0368 (5)
C5	1.0628 (2)	−0.7060 (2)	0.7879 (2)	0.0400 (5)
H5	1.1411	−0.7665	0.7643	0.041 (6)*
C6	1.0252 (2)	−0.5907 (2)	0.7231 (2)	0.0396 (5)
H6	1.0797	−0.5744	0.6575	0.045 (6)*
C7	0.8712 (2)	−0.3798 (2)	0.6796 (2)	0.0386 (5)
H7	0.9447	−0.3439	0.6674	0.041 (6)*
C8	0.7468 (2)	−0.3148 (2)	0.6271 (2)	0.0379 (5)
C9	0.6743 (2)	−0.5822 (3)	1.0555 (3)	0.0573 (7)
H9A	0.6962	−0.4967	1.1140	0.062 (8)*
H9B	0.6286	−0.6190	1.1181	0.067 (8)*
H9C	0.6152	−0.5708	0.9557	0.059 (7)*
C10	1.1345 (3)	−0.9351 (3)	0.9281 (4)	0.0639 (8)
H10A	1.1315	−0.9667	0.8146	0.077 (9)*
H10B	1.1419	−1.0099	0.9794	0.072 (8)*
H10C	1.2125	−0.8907	0.9715	0.083 (10)*
C11	0.7345 (2)	−0.1897 (2)	0.5624 (2)	0.0360 (5)
C12	0.6366 (2)	−0.1632 (2)	0.4271 (2)	0.0377 (5)
H12	0.5762	−0.2231	0.3787	0.042 (6)*
C13	0.6288 (2)	−0.0499 (2)	0.3652 (2)	0.0367 (5)
C14	0.7168 (2)	0.0425 (2)	0.4392 (2)	0.0387 (5)
C15	0.8126 (2)	0.0182 (2)	0.5723 (3)	0.0451 (6)
H15	0.8717	0.0791	0.6218	0.047 (6)*
C16	0.8209 (2)	−0.0976 (2)	0.6328 (2)	0.0426 (6)
H16	0.8861	−0.1130	0.7226	0.043 (6)*
C17	0.4600 (3)	−0.1159 (3)	0.1388 (3)	0.0578 (7)
H17A	0.5195	−0.1994	0.1096	0.070 (8)*
H17B	0.4093	−0.0857	0.0433	0.067 (7)*
H17C	0.3973	−0.1289	0.2013	0.079 (9)*
C18	0.7894 (3)	0.2468 (3)	0.4374 (4)	0.0682 (8)
H18A	0.7771	0.2851	0.5463	0.116 (13)*
H18B	0.7696	0.3168	0.3758	0.083 (9)*
H18C	0.8825	0.2021	0.4359	0.095 (11)*
C19	0.6162 (2)	−0.3603 (2)	0.6334 (3)	0.0513 (6)
H19A	0.5483	−0.3403	0.5412	0.047 (6)*
H19B	0.6338	−0.4569	0.6262	0.054 (7)*
O1	0.79704 (15)	−0.67112 (15)	1.02396 (19)	0.0504 (4)
O2	1.01262 (15)	−0.84333 (15)	0.95593 (18)	0.0488 (4)
O3	0.54010 (16)	−0.01772 (15)	0.23126 (18)	0.0493 (4)
O4	0.69887 (16)	0.15257 (15)	0.36958 (18)	0.0488 (4)
O5	0.56207 (18)	−0.2974 (2)	0.7766 (2)	0.0692 (6)
H5A	0.5126	−0.2259	0.7636	0.124 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0381 (12)	0.0357 (12)	0.0340 (11)	−0.0066 (10)	0.0080 (9)	0.0087 (9)
C2	0.0361 (12)	0.0375 (12)	0.0397 (12)	−0.0010 (10)	0.0106 (10)	0.0111 (10)
C3	0.0376 (12)	0.0421 (13)	0.0333 (11)	−0.0078 (10)	0.0093 (9)	0.0103 (10)
C4	0.0397 (12)	0.0357 (12)	0.0361 (11)	−0.0037 (10)	0.0064 (10)	0.0117 (10)
C5	0.0355 (12)	0.0446 (13)	0.0389 (12)	0.0038 (10)	0.0121 (10)	0.0104 (10)
C6	0.0379 (12)	0.0480 (13)	0.0361 (12)	−0.0057 (11)	0.0103 (10)	0.0122 (10)
C7	0.0410 (13)	0.0408 (13)	0.0384 (12)	−0.0088 (10)	0.0108 (10)	0.0111 (10)
C8	0.0401 (13)	0.0410 (12)	0.0343 (11)	−0.0063 (10)	0.0097 (9)	0.0077 (10)
C9	0.0435 (14)	0.0715 (19)	0.0662 (17)	−0.0016 (13)	0.0253 (13)	0.0249 (15)
C10	0.0635 (19)	0.0565 (16)	0.077 (2)	0.0169 (15)	0.0253 (15)	0.0349 (15)
C11	0.0375 (12)	0.0364 (12)	0.0362 (11)	−0.0013 (10)	0.0121 (10)	0.0104 (10)
C12	0.0343 (12)	0.0392 (13)	0.0404 (12)	−0.0066 (10)	0.0074 (10)	0.0081 (10)
C13	0.0327 (12)	0.0384 (12)	0.0378 (12)	0.0032 (10)	0.0064 (9)	0.0128 (10)
C14	0.0407 (13)	0.0345 (12)	0.0419 (12)	0.0007 (10)	0.0115 (10)	0.0116 (10)
C15	0.0478 (14)	0.0418 (13)	0.0449 (13)	−0.0104 (12)	0.0019 (11)	0.0092 (11)
C16	0.0463 (13)	0.0460 (13)	0.0351 (12)	−0.0052 (11)	0.0020 (11)	0.0137 (10)
C17	0.0500 (15)	0.0646 (18)	0.0564 (15)	−0.0124 (14)	−0.0102 (13)	0.0217 (14)
C18	0.079 (2)	0.0488 (15)	0.081 (2)	−0.0245 (16)	−0.0101 (16)	0.0293 (15)
C19	0.0438 (14)	0.0571 (16)	0.0621 (16)	−0.0098 (12)	0.0041 (12)	0.0328 (13)
O1	0.0462 (9)	0.0563 (10)	0.0599 (10)	0.0015 (8)	0.0244 (8)	0.0289 (8)
O2	0.0485 (10)	0.0454 (9)	0.0570 (10)	0.0063 (8)	0.0172 (8)	0.0244 (8)
O3	0.0479 (9)	0.0502 (10)	0.0486 (9)	−0.0075 (8)	−0.0070 (8)	0.0214 (8)
O4	0.0530 (10)	0.0377 (9)	0.0576 (10)	−0.0078 (8)	0.0006 (8)	0.0208 (8)
O5	0.0539 (11)	0.0836 (14)	0.0872 (14)	0.0157 (11)	0.0366 (10)	0.0532 (12)

Geometric parameters (Å, º)

C1—C6	1.381 (3)	C11—C16	1.380 (3)
C1—C2	1.403 (3)	C11—C12	1.408 (3)
C1—C7	1.468 (3)	C12—C13	1.379 (3)
C2—C3	1.380 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—O3	1.372 (2)
C3—O1	1.368 (2)	C13—C14	1.398 (3)
C3—C4	1.404 (3)	C14—O4	1.371 (2)
C4—O2	1.371 (2)	C14—C15	1.378 (3)
C4—C5	1.374 (3)	C15—C16	1.395 (3)
C5—C6	1.383 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—O3	1.426 (3)
C7—C8	1.338 (3)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—C11	1.497 (3)	C17—H17C	0.9600
C8—C19	1.504 (3)	C18—O4	1.421 (3)
C9—O1	1.419 (3)	C18—H18A	0.9600
C9—H9A	0.9600	C18—H18B	0.9600
C9—H9B	0.9600	C18—H18C	0.9600
C9—H9C	0.9600	C19—O5	1.425 (3)
C10—O2	1.418 (3)	C19—H19A	0.9700
C10—H10A	0.9600	C19—H19B	0.9700
C10—H10B	0.9600	O5—H5A	0.8200
C10—H10C	0.9600
C6—C1—C2	117.84 (18)	C13—C12—C11	121.1 (2)
C6—C1—C7	119.59 (19)	C13—C12—H12	119.5
C2—C1—C7	122.57 (19)	C11—C12—H12	119.5
C3—C2—C1	121.24 (19)	O3—C13—C12	125.3 (2)
C3—C2—H2	119.4	O3—C13—C14	114.73 (17)
C1—C2—H2	119.4	C12—C13—C14	120.00 (19)
O1—C3—C2	124.51 (19)	O4—C14—C15	125.2 (2)
O1—C3—C4	115.85 (17)	O4—C14—C13	115.22 (18)
C2—C3—C4	119.63 (19)	C15—C14—C13	119.58 (19)
O2—C4—C5	125.15 (19)	C14—C15—C16	120.0 (2)
O2—C4—C3	115.56 (18)	C14—C15—H15	120.0
C5—C4—C3	119.29 (18)	C16—C15—H15	120.0
C4—C5—C6	120.5 (2)	C11—C16—C15	121.4 (2)
C4—C5—H5	119.7	C11—C16—H16	119.3
C6—C5—H5	119.7	C15—C16—H16	119.3
C1—C6—C5	121.4 (2)	O3—C17—H17A	109.5
C1—C6—H6	119.3	O3—C17—H17B	109.5
C5—C6—H6	119.3	H17A—C17—H17B	109.5
C8—C7—C1	129.5 (2)	O3—C17—H17C	109.5
C8—C7—H7	115.2	H17A—C17—H17C	109.5
C1—C7—H7	115.2	H17B—C17—H17C	109.5
C7—C8—C11	119.7 (2)	O4—C18—H18A	109.5
C7—C8—C19	122.69 (19)	O4—C18—H18B	109.5
C11—C8—C19	117.62 (19)	H18A—C18—H18B	109.5
O1—C9—H9A	109.5	O4—C18—H18C	109.5
O1—C9—H9B	109.5	H18A—C18—H18C	109.5
H9A—C9—H9B	109.5	H18B—C18—H18C	109.5
O1—C9—H9C	109.5	O5—C19—C8	112.7 (2)
H9A—C9—H9C	109.5	O5—C19—H19A	109.1
H9B—C9—H9C	109.5	C8—C19—H19A	109.1
O2—C10—H10A	109.5	O5—C19—H19B	109.1
O2—C10—H10B	109.5	C8—C19—H19B	109.1
H10A—C10—H10B	109.5	H19A—C19—H19B	107.8
O2—C10—H10C	109.5	C3—O1—C9	116.66 (17)
H10A—C10—H10C	109.5	C4—O2—C10	116.69 (17)
H10B—C10—H10C	109.5	C13—O3—C17	117.32 (16)
C16—C11—C12	117.89 (19)	C14—O4—C18	117.16 (18)
C16—C11—C8	120.67 (18)	C19—O5—H5A	109.5
C12—C11—C8	121.4 (2)
C6—C1—C2—C3	−2.1 (3)	C8—C11—C12—C13	−177.90 (19)
C7—C1—C2—C3	178.6 (2)	C11—C12—C13—O3	177.86 (19)
C1—C2—C3—O1	179.9 (2)	C11—C12—C13—C14	−1.6 (3)
C1—C2—C3—C4	1.2 (3)	O3—C13—C14—O4	1.6 (3)
O1—C3—C4—O2	1.7 (3)	C12—C13—C14—O4	−178.93 (18)
C2—C3—C4—O2	−179.50 (19)	O3—C13—C14—C15	−178.32 (19)
O1—C3—C4—C5	−178.86 (19)	C12—C13—C14—C15	1.2 (3)
C2—C3—C4—C5	0.0 (3)	O4—C14—C15—C16	179.8 (2)
O2—C4—C5—C6	179.3 (2)	C13—C14—C15—C16	−0.3 (3)
C3—C4—C5—C6	−0.1 (3)	C12—C11—C16—C15	−0.2 (3)
C2—C1—C6—C5	2.0 (3)	C8—C11—C16—C15	178.8 (2)
C7—C1—C6—C5	−178.7 (2)	C14—C15—C16—C11	−0.2 (3)
C4—C5—C6—C1	−0.9 (3)	C7—C8—C19—O5	92.6 (3)
C6—C1—C7—C8	145.4 (2)	C11—C8—C19—O5	−86.0 (2)
C2—C1—C7—C8	−35.3 (3)	C2—C3—O1—C9	3.9 (3)
C1—C7—C8—C11	177.1 (2)	C4—C3—O1—C9	−177.4 (2)
C1—C7—C8—C19	−1.5 (4)	C5—C4—O2—C10	3.3 (3)
C7—C8—C11—C16	−38.7 (3)	C3—C4—O2—C10	−177.3 (2)
C19—C8—C11—C16	140.0 (2)	C12—C13—O3—C17	−7.2 (3)
C7—C8—C11—C12	140.3 (2)	C14—C13—O3—C17	172.23 (19)
C19—C8—C11—C12	−41.1 (3)	C15—C14—O4—C18	2.1 (3)
C16—C11—C12—C13	1.1 (3)	C13—C14—O4—C18	−177.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3^i	0.82	2.46	3.226 (2)	156
O5—H5A···O4^i	0.82	2.28	2.940 (2)	138
C2—H2···O5	0.93	2.48	3.277 (3)	144

Symmetry code: (i) −x+1, −y, −z+1.