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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.
Supporting information
CCDC reference: 239257
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.34 × 0.23 × 0.18 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0356P)2 + 0.1258P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.013 (3) |
Special details top
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<10.0σI) 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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O3i | 0.82 | 2.46 | 3.226 (2) | 156 |
O5—H5A···O4i | 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. |
Selected torsion angles (°) in (I) and the benzene solvate of (I) top | compound | |
Torsion angle | (I) | Benzene solvate of (I) |
C2—C1—C7—C8 | -35.3 (3) | 141.1 (3) |
C1—C7—C8—C11 | 177.1 (2) | -179.2 (3) |
C1—C7—C8—C19 | -1.5 (4) | -0.7 (5) |
C7—C8—C19—O5 | 92.6 (3) | 88.0 (3) |
C12—C11—C8—C7 | 140.3 (2) | -45.3 (4) |
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