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Triphenyl(2,4,5-trimethoxybenzyl)phosphonium chloride is formed in solvent-free form by the reaction under anhydrous conditions between triphenylphosphane and 2,4,5-trimethoxybenzyl chloride, but when it is crystallized from a mixture of ethyl acetate and chloroform in the presence of air it forms a stoichiometric monohydrate, C
28H
28O
3P
+·Cl
−·H
2O, (I). The reactions between the anhydrous phosphonium salt and alkoxy-substituted benzaldehydes, using Wittig reactions in the presence of potassium
tert-butoxide, provide a series of multiply substituted stilbenes, most of which were assigned the
Z configuration on the basis of their NMR spectra. However, no such deduction could be made for the symmetrically substituted (
Z)-2,2′,4,4′,5,5′-hexamethoxystilbene, C
20H
24O
6, (II). Compound (II) does in fact have the
Z configuration and the molecular geometry provides evidence for steric congestion around the central double bond; in particular, the central alkene fragment is nonplanar, with a C—C=C—C torsion angle of 7.8 (4)°. In hydrated salt (I), the chloride anions and water molecules are linked by O—H
Cl hydrogen bonds to form
C21(4) chains; each cation is linked by C—H
O hydrogen bonds to two different chains, so forming a sheet structure. There are no direction-specific intermolecular interactions in the structure of (II).
Supporting information
CCDC references: 1400448; 1400447
For both compounds, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis RED (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
(I) Triphenyl(3,4,5-trimethoxybenzyl)phosphonium chloride monohydrate
top
Crystal data top
C28H28O3P+·Cl−·H2O | F(000) = 1048 |
Mr = 496.94 | Dx = 1.339 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 14.5660 (4) Å | Cell parameters from 4719 reflections |
b = 15.8567 (3) Å | θ = 3.1–71.4° |
c = 11.0472 (3) Å | µ = 2.25 mm−1 |
β = 104.872 (3)° | T = 173 K |
V = 2466.08 (11) Å3 | Block, pink |
Z = 4 | 0.40 × 0.31 × 0.25 mm |
Data collection top
Agilent Eos Gemini diffractometer | 4209 reflections with I > 2σ(I) |
Radiation source: Enhance (Cu) X-ray source | Rint = 0.033 |
ω scans | θmax = 71.4°, θmin = 3.1° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −17→17 |
Tmin = 0.338, Tmax = 0.570 | k = −19→12 |
9522 measured reflections | l = −11→13 |
4719 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0655P)2 + 0.9657P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4719 reflections | Δρmax = 0.56 e Å−3 |
310 parameters | Δρmin = −0.31 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.29050 (3) | 0.38423 (3) | 0.59848 (4) | 0.01596 (12) | |
C7 | 0.19422 (12) | 0.45803 (11) | 0.59314 (16) | 0.0195 (3) | |
H7A | 0.1703 | 0.4499 | 0.6685 | 0.023* | |
H7B | 0.2192 | 0.5162 | 0.5955 | 0.023* | |
C1 | 0.11271 (12) | 0.44805 (11) | 0.47800 (16) | 0.0196 (3) | |
C2 | 0.03977 (12) | 0.39217 (11) | 0.47886 (16) | 0.0202 (3) | |
C3 | −0.03768 (12) | 0.38402 (12) | 0.37375 (17) | 0.0227 (4) | |
H3 | −0.0880 | 0.3462 | 0.3751 | 0.027* | |
C4 | −0.04009 (13) | 0.43175 (13) | 0.26794 (17) | 0.0247 (4) | |
C5 | 0.03427 (13) | 0.48777 (12) | 0.26544 (17) | 0.0249 (4) | |
C6 | 0.10916 (12) | 0.49630 (11) | 0.37115 (17) | 0.0220 (4) | |
H6 | 0.1586 | 0.5354 | 0.3710 | 0.026* | |
O2 | 0.04801 (9) | 0.34810 (9) | 0.58800 (12) | 0.0250 (3) | |
C211 | −0.01722 (15) | 0.28096 (14) | 0.5863 (2) | 0.0335 (5) | |
H21A | −0.0143 | 0.2412 | 0.5194 | 0.050* | |
H21B | −0.0817 | 0.3038 | 0.5711 | 0.050* | |
H21C | −0.0005 | 0.2517 | 0.6671 | 0.050* | |
O4 | −0.11330 (10) | 0.43079 (11) | 0.16142 (13) | 0.0356 (3) | |
C411 | −0.18810 (15) | 0.37152 (15) | 0.1551 (2) | 0.0346 (5) | |
H41A | −0.2196 | 0.3836 | 0.2216 | 0.052* | |
H41B | −0.1618 | 0.3143 | 0.1660 | 0.052* | |
H41C | −0.2343 | 0.3759 | 0.0734 | 0.052* | |
O5 | 0.02547 (10) | 0.53155 (10) | 0.15638 (13) | 0.0358 (4) | |
C511 | 0.10087 (17) | 0.58634 (15) | 0.1496 (2) | 0.0374 (5) | |
H51A | 0.1609 | 0.5550 | 0.1703 | 0.056* | |
H51B | 0.1045 | 0.6328 | 0.2092 | 0.056* | |
H51C | 0.0894 | 0.6092 | 0.0646 | 0.056* | |
C11 | 0.35395 (12) | 0.41233 (11) | 0.48458 (15) | 0.0191 (3) | |
C12 | 0.35342 (12) | 0.49557 (11) | 0.44333 (17) | 0.0215 (4) | |
H12 | 0.3180 | 0.5374 | 0.4732 | 0.026* | |
C13 | 0.40520 (13) | 0.51680 (12) | 0.35813 (18) | 0.0252 (4) | |
H13 | 0.4032 | 0.5729 | 0.3272 | 0.030* | |
C14 | 0.45964 (13) | 0.45657 (13) | 0.31817 (17) | 0.0263 (4) | |
H14 | 0.4950 | 0.4716 | 0.2601 | 0.032* | |
C15 | 0.46292 (13) | 0.37421 (12) | 0.36246 (18) | 0.0261 (4) | |
H15 | 0.5020 | 0.3336 | 0.3368 | 0.031* | |
C16 | 0.40888 (12) | 0.35148 (12) | 0.44433 (17) | 0.0219 (4) | |
H16 | 0.4093 | 0.2949 | 0.4727 | 0.026* | |
C21 | 0.36953 (12) | 0.38576 (11) | 0.75326 (16) | 0.0189 (3) | |
C22 | 0.34202 (13) | 0.42230 (13) | 0.85333 (18) | 0.0270 (4) | |
H22 | 0.2821 | 0.4494 | 0.8400 | 0.032* | |
C23 | 0.40302 (15) | 0.41875 (15) | 0.97277 (19) | 0.0339 (5) | |
H23 | 0.3846 | 0.4434 | 1.0413 | 0.041* | |
C24 | 0.49029 (15) | 0.37959 (14) | 0.99246 (19) | 0.0320 (4) | |
H24 | 0.5313 | 0.3770 | 1.0745 | 0.038* | |
C25 | 0.51838 (13) | 0.34412 (13) | 0.89312 (18) | 0.0271 (4) | |
H25 | 0.5789 | 0.3180 | 0.9070 | 0.033* | |
C26 | 0.45825 (12) | 0.34671 (11) | 0.77333 (17) | 0.0223 (4) | |
H26 | 0.4773 | 0.3221 | 0.7052 | 0.027* | |
C31 | 0.24490 (12) | 0.27924 (10) | 0.56497 (16) | 0.0178 (3) | |
C32 | 0.19173 (12) | 0.25865 (12) | 0.44395 (16) | 0.0211 (4) | |
H32 | 0.1837 | 0.2987 | 0.3782 | 0.025* | |
C33 | 0.15094 (13) | 0.17956 (12) | 0.42086 (17) | 0.0253 (4) | |
H33 | 0.1149 | 0.1655 | 0.3388 | 0.030* | |
C34 | 0.16222 (14) | 0.12040 (12) | 0.5165 (2) | 0.0283 (4) | |
H34 | 0.1334 | 0.0664 | 0.5002 | 0.034* | |
C35 | 0.21587 (14) | 0.14078 (13) | 0.63610 (18) | 0.0273 (4) | |
H35 | 0.2243 | 0.1004 | 0.7015 | 0.033* | |
C36 | 0.25721 (12) | 0.21989 (12) | 0.66038 (16) | 0.0224 (4) | |
H36 | 0.2939 | 0.2335 | 0.7423 | 0.027* | |
O1W | 0.62816 (13) | 0.26774 (13) | 0.66686 (17) | 0.0509 (5) | |
H111 | 0.6715 | 0.2749 | 0.6248 | 0.076* | |
H112 | 0.6670 | 0.2485 | 0.7474 | 0.076* | |
Cl1 | 0.72871 (3) | 0.31459 (3) | 0.43891 (5) | 0.03452 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0146 (2) | 0.0171 (2) | 0.0155 (2) | −0.00040 (14) | 0.00259 (15) | 0.00018 (15) |
C7 | 0.0173 (8) | 0.0202 (8) | 0.0206 (8) | 0.0022 (6) | 0.0042 (6) | −0.0004 (6) |
C1 | 0.0170 (8) | 0.0201 (8) | 0.0213 (8) | 0.0045 (6) | 0.0039 (6) | −0.0004 (7) |
C2 | 0.0191 (8) | 0.0220 (8) | 0.0195 (8) | 0.0048 (6) | 0.0048 (7) | 0.0005 (6) |
C3 | 0.0176 (8) | 0.0250 (9) | 0.0251 (9) | 0.0004 (6) | 0.0050 (7) | −0.0029 (7) |
C4 | 0.0198 (8) | 0.0316 (10) | 0.0201 (8) | 0.0049 (7) | 0.0003 (7) | −0.0019 (7) |
C5 | 0.0239 (9) | 0.0294 (9) | 0.0211 (9) | 0.0063 (7) | 0.0054 (7) | 0.0042 (7) |
C6 | 0.0186 (8) | 0.0217 (9) | 0.0256 (9) | 0.0035 (6) | 0.0055 (7) | 0.0026 (7) |
O2 | 0.0215 (6) | 0.0289 (7) | 0.0233 (6) | −0.0025 (5) | 0.0034 (5) | 0.0039 (5) |
C211 | 0.0282 (10) | 0.0370 (11) | 0.0340 (11) | −0.0085 (8) | 0.0057 (8) | 0.0085 (9) |
O4 | 0.0262 (7) | 0.0525 (9) | 0.0225 (7) | −0.0040 (6) | −0.0042 (5) | 0.0047 (6) |
C411 | 0.0251 (9) | 0.0453 (12) | 0.0288 (10) | −0.0018 (9) | −0.0015 (8) | −0.0072 (9) |
O5 | 0.0313 (7) | 0.0495 (9) | 0.0243 (7) | 0.0014 (6) | 0.0026 (6) | 0.0146 (6) |
C511 | 0.0430 (12) | 0.0365 (11) | 0.0341 (11) | 0.0039 (9) | 0.0122 (9) | 0.0121 (9) |
C11 | 0.0163 (7) | 0.0233 (9) | 0.0170 (8) | −0.0021 (6) | 0.0030 (6) | −0.0001 (6) |
C12 | 0.0185 (8) | 0.0218 (9) | 0.0226 (8) | −0.0011 (6) | 0.0021 (7) | −0.0004 (7) |
C13 | 0.0234 (8) | 0.0255 (9) | 0.0246 (9) | −0.0054 (7) | 0.0024 (7) | 0.0045 (7) |
C14 | 0.0231 (9) | 0.0348 (10) | 0.0219 (9) | −0.0094 (7) | 0.0076 (7) | −0.0031 (7) |
C15 | 0.0230 (9) | 0.0299 (10) | 0.0267 (9) | −0.0034 (7) | 0.0088 (7) | −0.0080 (8) |
C16 | 0.0217 (8) | 0.0210 (8) | 0.0222 (8) | −0.0022 (7) | 0.0045 (7) | −0.0021 (7) |
C21 | 0.0183 (8) | 0.0197 (8) | 0.0171 (8) | −0.0042 (6) | 0.0016 (6) | 0.0010 (6) |
C22 | 0.0232 (9) | 0.0333 (10) | 0.0226 (9) | 0.0008 (7) | 0.0024 (7) | −0.0033 (8) |
C23 | 0.0345 (10) | 0.0452 (12) | 0.0197 (9) | −0.0020 (9) | 0.0029 (8) | −0.0080 (8) |
C24 | 0.0302 (10) | 0.0368 (11) | 0.0228 (9) | −0.0046 (8) | −0.0045 (8) | 0.0004 (8) |
C25 | 0.0210 (8) | 0.0279 (10) | 0.0285 (9) | −0.0006 (7) | −0.0009 (7) | 0.0045 (8) |
C26 | 0.0206 (8) | 0.0232 (9) | 0.0218 (8) | −0.0023 (7) | 0.0033 (7) | 0.0014 (7) |
C31 | 0.0168 (7) | 0.0158 (8) | 0.0209 (8) | −0.0010 (6) | 0.0050 (6) | −0.0005 (6) |
C32 | 0.0208 (8) | 0.0235 (9) | 0.0185 (8) | 0.0028 (7) | 0.0040 (6) | 0.0007 (7) |
C33 | 0.0239 (9) | 0.0273 (9) | 0.0215 (9) | −0.0007 (7) | 0.0002 (7) | −0.0059 (7) |
C34 | 0.0277 (9) | 0.0224 (9) | 0.0327 (10) | −0.0054 (7) | 0.0039 (8) | −0.0026 (8) |
C35 | 0.0305 (9) | 0.0236 (9) | 0.0264 (9) | −0.0035 (7) | 0.0045 (7) | 0.0042 (7) |
C36 | 0.0227 (8) | 0.0243 (9) | 0.0182 (8) | −0.0013 (7) | 0.0018 (6) | 0.0009 (7) |
O1W | 0.0402 (9) | 0.0675 (12) | 0.0457 (10) | 0.0153 (8) | 0.0127 (8) | 0.0077 (9) |
Cl1 | 0.0279 (2) | 0.0370 (3) | 0.0400 (3) | −0.00231 (18) | 0.0112 (2) | −0.0033 (2) |
Geometric parameters (Å, º) top
P1—C31 | 1.7954 (17) | C12—H12 | 0.9500 |
P1—C11 | 1.7981 (17) | C13—C14 | 1.384 (3) |
P1—C21 | 1.7998 (17) | C13—H13 | 0.9500 |
P1—C7 | 1.8159 (17) | C14—C15 | 1.391 (3) |
C7—C1 | 1.509 (2) | C14—H14 | 0.9500 |
C7—H7A | 0.9900 | C15—C16 | 1.390 (3) |
C7—H7B | 0.9900 | C15—H15 | 0.9500 |
C1—C2 | 1.385 (3) | C16—H16 | 0.9500 |
C1—C6 | 1.396 (3) | C21—C22 | 1.395 (3) |
C2—O2 | 1.372 (2) | C21—C26 | 1.398 (2) |
C2—C3 | 1.402 (2) | C22—C23 | 1.390 (3) |
C3—C4 | 1.385 (3) | C22—H22 | 0.9500 |
C3—H3 | 0.9500 | C23—C24 | 1.381 (3) |
C4—O4 | 1.370 (2) | C23—H23 | 0.9500 |
C4—C5 | 1.407 (3) | C24—C25 | 1.385 (3) |
C5—O5 | 1.368 (2) | C24—H24 | 0.9500 |
C5—C6 | 1.385 (3) | C25—C26 | 1.387 (3) |
C6—H6 | 0.9500 | C25—H25 | 0.9500 |
O2—C211 | 1.424 (2) | C26—H26 | 0.9500 |
C211—H21A | 0.9800 | C31—C36 | 1.390 (2) |
C211—H21B | 0.9800 | C31—C32 | 1.401 (2) |
C211—H21C | 0.9800 | C32—C33 | 1.383 (3) |
O4—C411 | 1.427 (3) | C32—H32 | 0.9500 |
C411—H41A | 0.9800 | C33—C34 | 1.391 (3) |
C411—H41B | 0.9800 | C33—H33 | 0.9500 |
C411—H41C | 0.9800 | C34—C35 | 1.389 (3) |
O5—C511 | 1.417 (3) | C34—H34 | 0.9500 |
C511—H51A | 0.9800 | C35—C36 | 1.388 (3) |
C511—H51B | 0.9800 | C35—H35 | 0.9500 |
C511—H51C | 0.9800 | C36—H36 | 0.9500 |
C11—C12 | 1.396 (3) | O1W—H111 | 0.8817 |
C11—C16 | 1.397 (3) | O1W—H112 | 0.9726 |
C12—C13 | 1.390 (3) | | |
| | | |
C31—P1—C11 | 108.36 (8) | C16—C11—P1 | 119.39 (14) |
C31—P1—C21 | 108.73 (8) | C13—C12—C11 | 119.44 (17) |
C11—P1—C21 | 110.07 (8) | C13—C12—H12 | 120.3 |
C31—P1—C7 | 110.43 (8) | C11—C12—H12 | 120.3 |
C11—P1—C7 | 110.42 (8) | C14—C13—C12 | 120.25 (18) |
C21—P1—C7 | 108.81 (8) | C14—C13—H13 | 119.9 |
C1—C7—P1 | 113.18 (12) | C12—C13—H13 | 119.9 |
C1—C7—H7A | 108.9 | C13—C14—C15 | 120.42 (17) |
P1—C7—H7A | 108.9 | C13—C14—H14 | 119.8 |
C1—C7—H7B | 108.9 | C15—C14—H14 | 119.8 |
P1—C7—H7B | 108.9 | C16—C15—C14 | 119.88 (18) |
H7A—C7—H7B | 107.8 | C16—C15—H15 | 120.1 |
C2—C1—C6 | 119.61 (16) | C14—C15—H15 | 120.1 |
C2—C1—C7 | 120.01 (16) | C15—C16—C11 | 119.61 (17) |
C6—C1—C7 | 120.36 (16) | C15—C16—H16 | 120.2 |
C1—C2—O2 | 115.94 (15) | C11—C16—H16 | 120.2 |
C3—C2—O2 | 123.46 (16) | C22—C21—C26 | 120.00 (16) |
C2—O2—C211 | 117.48 (14) | C22—C21—P1 | 120.98 (14) |
C1—C2—C3 | 120.58 (16) | C26—C21—P1 | 118.97 (14) |
C4—C3—C2 | 119.29 (17) | C23—C22—C21 | 119.46 (18) |
C4—C3—H3 | 120.4 | C23—C22—H22 | 120.3 |
C2—C3—H3 | 120.4 | C21—C22—H22 | 120.3 |
C3—C4—O4 | 124.33 (17) | C24—C23—C22 | 120.40 (19) |
C5—C4—O4 | 115.07 (17) | C24—C23—H23 | 119.8 |
C4—O4—C411 | 117.75 (16) | C22—C23—H23 | 119.8 |
C3—C4—C5 | 120.58 (16) | C23—C24—C25 | 120.33 (18) |
C4—C5—O5 | 116.06 (16) | C23—C24—H24 | 119.8 |
C6—C5—O5 | 124.66 (18) | C25—C24—H24 | 119.8 |
C5—O5—C511 | 117.31 (16) | C24—C25—C26 | 120.07 (18) |
C6—C5—C4 | 119.28 (17) | C24—C25—H25 | 120.0 |
C5—C6—C1 | 120.63 (17) | C26—C25—H25 | 120.0 |
C5—C6—H6 | 119.7 | C25—C26—C21 | 119.72 (17) |
C1—C6—H6 | 119.7 | C25—C26—H26 | 120.1 |
O2—C211—H21A | 109.5 | C21—C26—H26 | 120.1 |
O2—C211—H21B | 109.5 | C36—C31—C32 | 119.87 (16) |
H21A—C211—H21B | 109.5 | C36—C31—P1 | 120.17 (13) |
O2—C211—H21C | 109.5 | C32—C31—P1 | 119.84 (13) |
H21A—C211—H21C | 109.5 | C33—C32—C31 | 119.57 (16) |
H21B—C211—H21C | 109.5 | C33—C32—H32 | 120.2 |
O4—C411—H41A | 109.5 | C31—C32—H32 | 120.2 |
O4—C411—H41B | 109.5 | C32—C33—C34 | 120.66 (17) |
H41A—C411—H41B | 109.5 | C32—C33—H33 | 119.7 |
O4—C411—H41C | 109.5 | C34—C33—H33 | 119.7 |
H41A—C411—H41C | 109.5 | C35—C34—C33 | 119.57 (17) |
H41B—C411—H41C | 109.5 | C35—C34—H34 | 120.2 |
O5—C511—H51A | 109.5 | C33—C34—H34 | 120.2 |
O5—C511—H51B | 109.5 | C36—C35—C34 | 120.29 (17) |
H51A—C511—H51B | 109.5 | C36—C35—H35 | 119.9 |
O5—C511—H51C | 109.5 | C34—C35—H35 | 119.9 |
H51A—C511—H51C | 109.5 | C35—C36—C31 | 120.03 (16) |
H51B—C511—H51C | 109.5 | C35—C36—H36 | 120.0 |
C12—C11—C16 | 120.33 (16) | C31—C36—H36 | 120.0 |
C12—C11—P1 | 120.14 (14) | H111—O1W—H112 | 101.3 |
| | | |
C1—C7—P1—C11 | 71.96 (14) | C16—C11—C12—C13 | 2.4 (3) |
C1—C7—P1—C21 | −167.13 (12) | P1—C11—C12—C13 | 178.04 (13) |
C1—C7—P1—C31 | −47.87 (15) | C11—C12—C13—C14 | −2.4 (3) |
P1—C7—C1—C2 | 88.41 (17) | C12—C13—C14—C15 | 0.2 (3) |
C3—C2—O2—C211 | 10.9 (3) | C13—C14—C15—C16 | 2.0 (3) |
P1—C7—C1—C6 | −93.06 (18) | C14—C15—C16—C11 | −2.0 (3) |
C6—C1—C2—O2 | −179.09 (15) | C12—C11—C16—C15 | −0.2 (3) |
C7—C1—C2—O2 | −0.6 (2) | P1—C11—C16—C15 | −175.86 (13) |
C6—C1—C2—C3 | −0.3 (3) | C31—P1—C21—C22 | −105.49 (16) |
C7—C1—C2—C3 | 178.20 (16) | C11—P1—C21—C22 | 135.96 (15) |
O2—C2—C3—C4 | 179.48 (16) | C31—P1—C21—C26 | 72.04 (15) |
C1—C2—C3—C4 | 0.8 (3) | C11—P1—C21—C26 | −46.51 (16) |
C2—C3—C4—O4 | −178.01 (18) | C7—P1—C21—C26 | −167.64 (14) |
C2—C3—C4—C5 | 0.1 (3) | C26—C21—C22—C23 | −0.6 (3) |
O4—C4—C5—O5 | −2.1 (3) | P1—C21—C22—C23 | 176.88 (16) |
C3—C4—C5—O5 | 179.59 (17) | C21—C22—C23—C24 | 0.1 (3) |
O4—C4—C5—C6 | 176.78 (17) | C22—C23—C24—C25 | 0.6 (3) |
C3—C4—C5—C6 | −1.5 (3) | C23—C24—C25—C26 | −0.9 (3) |
O5—C5—C6—C1 | −179.20 (17) | C24—C25—C26—C21 | 0.4 (3) |
C4—C5—C6—C1 | 2.0 (3) | C22—C21—C26—C25 | 0.3 (3) |
C2—C1—C6—C5 | −1.1 (3) | P1—C21—C26—C25 | −177.22 (14) |
C7—C1—C6—C5 | −179.63 (16) | C11—P1—C31—C36 | 132.16 (14) |
C1—C2—O2—C211 | −170.40 (17) | C21—P1—C31—C36 | 12.54 (16) |
C7—P1—C11—C12 | 24.95 (16) | C7—P1—C31—C36 | −106.77 (15) |
C7—P1—C21—C22 | 14.84 (18) | C11—P1—C31—C32 | −51.79 (15) |
C7—P1—C31—C32 | 69.27 (15) | C21—P1—C31—C32 | −171.41 (14) |
C3—C4—O4—C411 | −5.6 (3) | C36—C31—C32—C33 | 0.8 (3) |
C5—C4—O4—C411 | 176.20 (17) | P1—C31—C32—C33 | −175.30 (14) |
C6—C5—O5—C511 | 3.3 (3) | C31—C32—C33—C34 | 0.0 (3) |
C4—C5—O5—C511 | −177.91 (18) | C32—C33—C34—C35 | −0.7 (3) |
C31—P1—C11—C12 | 146.02 (14) | C33—C34—C35—C36 | 0.6 (3) |
C21—P1—C11—C12 | −95.20 (15) | C34—C35—C36—C31 | 0.1 (3) |
C31—P1—C11—C16 | −38.31 (16) | C32—C31—C36—C35 | −0.8 (3) |
C21—P1—C11—C16 | 80.46 (15) | P1—C31—C36—C35 | 175.22 (14) |
C7—P1—C11—C16 | −159.38 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H111···Cl1 | 0.88 | 2.49 | 3.306 (2) | 155 |
O1W—H112···Cl1i | 0.97 | 2.30 | 3.2592 (19) | 167 |
C13—H13···O1Wii | 0.95 | 2.57 | 3.452 (3) | 154 |
C26—H26···O1W | 0.95 | 2.50 | 3.251 (3) | 136 |
C12—H12···Cl1ii | 0.95 | 2.69 | 3.6033 (18) | 161 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1. |
(II) (
Z)-2,2',4,4',5,5'-Hexamethoxystilbene
top
Crystal data top
C20H24O6 | F(000) = 768 |
Mr = 360.39 | Dx = 1.311 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 17.0340 (7) Å | Cell parameters from 3466 reflections |
b = 5.0747 (2) Å | θ = 4.1–71.2° |
c = 22.6111 (10) Å | µ = 0.80 mm−1 |
β = 110.917 (5)° | T = 173 K |
V = 1825.75 (14) Å3 | Needle, colourless |
Z = 4 | 0.49 × 0.06 × 0.04 mm |
Data collection top
Agilent Eos Gemini diffractometer | 2814 reflections with I > 2σ(I) |
Radiation source: Enhance (Cu) X-ray source | Rint = 0.031 |
ω scans | θmax = 71.2°, θmin = 4.1° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −15→20 |
Tmin = 0.713, Tmax = 0.969 | k = −5→6 |
6599 measured reflections | l = −26→27 |
3453 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.0869P)2 + 0.1034P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
3453 reflections | Δρmax = 0.27 e Å−3 |
241 parameters | Δρmin = −0.25 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.38819 (10) | 0.5381 (4) | 0.43151 (8) | 0.0290 (4) | |
H1 | 0.4463 | 0.5305 | 0.4566 | 0.035* | |
C11 | 0.36955 (10) | 0.6376 (3) | 0.36673 (8) | 0.0238 (4) | |
C12 | 0.42253 (10) | 0.8261 (4) | 0.35547 (8) | 0.0254 (4) | |
C13 | 0.40825 (10) | 0.9177 (3) | 0.29432 (8) | 0.0258 (4) | |
H13 | 0.4440 | 1.0486 | 0.2875 | 0.031* | |
C14 | 0.34197 (11) | 0.8180 (3) | 0.24348 (8) | 0.0235 (4) | |
C15 | 0.28932 (10) | 0.6233 (3) | 0.25352 (8) | 0.0226 (3) | |
C16 | 0.30433 (10) | 0.5350 (3) | 0.31446 (8) | 0.0229 (3) | |
H16 | 0.2694 | 0.4009 | 0.3211 | 0.027* | |
O12 | 0.48770 (9) | 0.9093 (3) | 0.40748 (7) | 0.0395 (4) | |
C121 | 0.53989 (12) | 1.1147 (4) | 0.40051 (10) | 0.0344 (4) | |
H12A | 0.5660 | 1.0609 | 0.3702 | 0.052* | |
H12B | 0.5837 | 1.1520 | 0.4416 | 0.052* | |
H12C | 0.5061 | 1.2735 | 0.3849 | 0.052* | |
O14 | 0.32261 (9) | 0.8951 (3) | 0.18190 (6) | 0.0325 (3) | |
C141 | 0.37063 (13) | 1.1038 (4) | 0.16999 (9) | 0.0340 (4) | |
H14A | 0.3501 | 1.1423 | 0.1245 | 0.051* | |
H14B | 0.4299 | 1.0516 | 0.1840 | 0.051* | |
H14C | 0.3650 | 1.2613 | 0.1932 | 0.051* | |
O15 | 0.22667 (8) | 0.5331 (3) | 0.20043 (6) | 0.0321 (3) | |
C151 | 0.17237 (12) | 0.3385 (4) | 0.20989 (9) | 0.0345 (4) | |
H15A | 0.1304 | 0.2883 | 0.1690 | 0.052* | |
H15B | 0.1440 | 0.4096 | 0.2373 | 0.052* | |
H15C | 0.2053 | 0.1832 | 0.2300 | 0.052* | |
C2 | 0.33687 (11) | 0.4565 (4) | 0.46092 (8) | 0.0266 (4) | |
H2 | 0.3648 | 0.3795 | 0.5013 | 0.032* | |
C21 | 0.24498 (10) | 0.4653 (3) | 0.44168 (7) | 0.0211 (3) | |
C22 | 0.20550 (10) | 0.2941 (3) | 0.47111 (8) | 0.0214 (3) | |
C23 | 0.11869 (10) | 0.3011 (3) | 0.45601 (8) | 0.0244 (4) | |
H23 | 0.0929 | 0.1837 | 0.4763 | 0.029* | |
C24 | 0.06988 (10) | 0.4784 (3) | 0.41154 (8) | 0.0247 (4) | |
C25 | 0.10805 (10) | 0.6560 (3) | 0.38227 (8) | 0.0218 (3) | |
C26 | 0.19414 (10) | 0.6489 (3) | 0.39806 (8) | 0.0215 (3) | |
H26 | 0.2198 | 0.7716 | 0.3789 | 0.026* | |
O22 | 0.25701 (7) | 0.1233 (2) | 0.51472 (6) | 0.0279 (3) | |
C221 | 0.21943 (12) | −0.0434 (4) | 0.54772 (9) | 0.0304 (4) | |
H22A | 0.1793 | −0.1619 | 0.5176 | 0.046* | |
H22B | 0.1900 | 0.0644 | 0.5692 | 0.046* | |
H22C | 0.2631 | −0.1476 | 0.5791 | 0.046* | |
O24 | −0.01539 (8) | 0.4969 (3) | 0.39321 (7) | 0.0377 (4) | |
C241 | −0.05734 (12) | 0.3007 (4) | 0.41562 (11) | 0.0387 (5) | |
H24A | −0.1182 | 0.3257 | 0.3960 | 0.058* | |
H24B | −0.0405 | 0.3152 | 0.4617 | 0.058* | |
H24C | −0.0422 | 0.1259 | 0.4046 | 0.058* | |
O25 | 0.05429 (8) | 0.8244 (3) | 0.33919 (6) | 0.0300 (3) | |
C251 | 0.09023 (12) | 0.9893 (4) | 0.30469 (9) | 0.0318 (4) | |
H25A | 0.0458 | 1.0920 | 0.2735 | 0.048* | |
H25B | 0.1188 | 0.8803 | 0.2828 | 0.048* | |
H25C | 0.1309 | 1.1093 | 0.3340 | 0.048* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0158 (7) | 0.0466 (10) | 0.0230 (8) | −0.0009 (7) | 0.0050 (7) | 0.0050 (7) |
C11 | 0.0180 (7) | 0.0325 (9) | 0.0227 (8) | 0.0013 (6) | 0.0093 (7) | 0.0029 (7) |
C12 | 0.0177 (8) | 0.0340 (9) | 0.0244 (8) | −0.0018 (6) | 0.0074 (7) | −0.0006 (7) |
C13 | 0.0234 (8) | 0.0288 (8) | 0.0276 (9) | −0.0041 (6) | 0.0122 (7) | 0.0013 (7) |
C14 | 0.0268 (8) | 0.0263 (8) | 0.0212 (8) | −0.0003 (6) | 0.0130 (7) | 0.0006 (6) |
C15 | 0.0199 (8) | 0.0275 (8) | 0.0203 (8) | −0.0018 (6) | 0.0072 (7) | −0.0023 (6) |
C16 | 0.0186 (7) | 0.0285 (8) | 0.0237 (8) | −0.0018 (6) | 0.0102 (7) | 0.0012 (6) |
O12 | 0.0293 (7) | 0.0557 (9) | 0.0284 (7) | −0.0171 (6) | 0.0039 (6) | 0.0015 (6) |
C121 | 0.0246 (9) | 0.0380 (10) | 0.0405 (10) | −0.0081 (7) | 0.0114 (8) | −0.0100 (8) |
O14 | 0.0399 (7) | 0.0372 (7) | 0.0217 (6) | −0.0097 (6) | 0.0125 (6) | 0.0028 (5) |
C141 | 0.0438 (11) | 0.0319 (9) | 0.0326 (10) | −0.0052 (8) | 0.0215 (9) | 0.0033 (7) |
O15 | 0.0322 (7) | 0.0409 (7) | 0.0217 (6) | −0.0135 (6) | 0.0078 (5) | −0.0013 (5) |
C151 | 0.0299 (9) | 0.0385 (10) | 0.0314 (10) | −0.0124 (8) | 0.0063 (8) | −0.0004 (8) |
C2 | 0.0229 (8) | 0.0355 (9) | 0.0199 (8) | −0.0012 (7) | 0.0058 (7) | 0.0044 (7) |
C21 | 0.0218 (8) | 0.0246 (8) | 0.0185 (7) | −0.0029 (6) | 0.0092 (6) | −0.0009 (6) |
C22 | 0.0250 (8) | 0.0212 (7) | 0.0189 (8) | −0.0001 (6) | 0.0087 (7) | 0.0005 (6) |
C23 | 0.0243 (8) | 0.0249 (8) | 0.0271 (8) | −0.0038 (6) | 0.0130 (7) | 0.0035 (6) |
C24 | 0.0190 (8) | 0.0278 (8) | 0.0287 (9) | −0.0019 (6) | 0.0103 (7) | 0.0018 (7) |
C25 | 0.0226 (8) | 0.0211 (7) | 0.0217 (8) | 0.0004 (6) | 0.0078 (7) | 0.0019 (6) |
C26 | 0.0239 (8) | 0.0223 (7) | 0.0216 (8) | −0.0027 (6) | 0.0120 (7) | 0.0010 (6) |
O22 | 0.0237 (6) | 0.0322 (6) | 0.0275 (6) | −0.0010 (5) | 0.0086 (5) | 0.0100 (5) |
C221 | 0.0320 (9) | 0.0329 (9) | 0.0269 (9) | −0.0031 (7) | 0.0111 (8) | 0.0097 (7) |
O24 | 0.0196 (6) | 0.0427 (8) | 0.0524 (9) | 0.0009 (5) | 0.0149 (6) | 0.0178 (6) |
C241 | 0.0227 (8) | 0.0478 (11) | 0.0464 (12) | −0.0087 (8) | 0.0135 (9) | 0.0081 (9) |
O25 | 0.0240 (6) | 0.0303 (6) | 0.0355 (7) | 0.0030 (5) | 0.0102 (6) | 0.0120 (5) |
C251 | 0.0324 (9) | 0.0297 (9) | 0.0322 (9) | 0.0009 (7) | 0.0103 (8) | 0.0110 (7) |
Geometric parameters (Å, º) top
C1—C2 | 1.339 (2) | C2—C21 | 1.468 (2) |
C1—C11 | 1.473 (2) | C2—H2 | 0.9500 |
C1—H1 | 0.9500 | C21—C22 | 1.403 (2) |
C11—C12 | 1.400 (2) | C21—C26 | 1.407 (2) |
C11—C16 | 1.402 (2) | C22—O22 | 1.370 (2) |
C12—O12 | 1.364 (2) | C22—C23 | 1.394 (2) |
C12—C13 | 1.395 (2) | C23—C24 | 1.384 (2) |
C13—C14 | 1.388 (3) | C23—H23 | 0.9500 |
C13—H13 | 0.9500 | C24—O24 | 1.364 (2) |
C14—O14 | 1.369 (2) | C24—C25 | 1.407 (2) |
C14—C15 | 1.406 (2) | C25—O25 | 1.371 (2) |
C15—O15 | 1.369 (2) | C25—C26 | 1.380 (2) |
C15—C16 | 1.383 (2) | C26—H26 | 0.9500 |
C16—H16 | 0.9500 | O22—C221 | 1.422 (2) |
O12—C121 | 1.415 (2) | C221—H22A | 0.9800 |
C121—H12A | 0.9800 | C221—H22B | 0.9800 |
C121—H12B | 0.9800 | C221—H22C | 0.9800 |
C121—H12C | 0.9800 | O24—C241 | 1.420 (2) |
O14—C141 | 1.421 (2) | C241—H24A | 0.9800 |
C141—H14A | 0.9800 | C241—H24B | 0.9800 |
C141—H14B | 0.9800 | C241—H24C | 0.9800 |
C141—H14C | 0.9800 | O25—C251 | 1.423 (2) |
O15—C151 | 1.421 (2) | C251—H25A | 0.9800 |
C151—H15A | 0.9800 | C251—H25B | 0.9800 |
C151—H15B | 0.9800 | C251—H25C | 0.9800 |
C151—H15C | 0.9800 | | |
| | | |
C2—C1—C11 | 130.75 (16) | C1—C2—C21 | 131.26 (16) |
C2—C1—H1 | 114.6 | C1—C2—H2 | 114.4 |
C11—C1—H1 | 114.6 | C21—C2—H2 | 114.4 |
C12—C11—C16 | 117.97 (15) | C22—C21—C26 | 117.58 (14) |
C12—C11—C1 | 119.42 (16) | C22—C21—C2 | 118.77 (15) |
C16—C11—C1 | 122.40 (15) | C26—C21—C2 | 123.51 (15) |
O12—C12—C11 | 115.72 (16) | O22—C22—C21 | 116.17 (14) |
O12—C12—C13 | 123.46 (15) | O22—C22—C23 | 122.90 (14) |
C13—C12—C11 | 120.82 (16) | C23—C22—C21 | 120.93 (15) |
C14—C13—C12 | 120.12 (15) | C24—C23—C22 | 120.27 (15) |
C14—C13—H13 | 119.9 | C24—C23—H23 | 119.9 |
C12—C13—H13 | 119.9 | C22—C23—H23 | 119.9 |
O14—C14—C13 | 124.60 (15) | O24—C24—C23 | 124.34 (15) |
O14—C14—C15 | 115.41 (15) | O24—C24—C25 | 115.68 (15) |
C13—C14—C15 | 119.99 (15) | C23—C24—C25 | 119.97 (15) |
O15—C15—C14 | 115.84 (15) | O25—C25—C24 | 115.46 (14) |
O15—C15—C16 | 125.03 (15) | O25—C25—C26 | 125.32 (14) |
C16—C15—C14 | 119.13 (16) | C26—C25—C24 | 119.22 (15) |
C15—C16—C11 | 121.91 (15) | C25—C26—C21 | 121.98 (14) |
C15—C16—H16 | 119.0 | C25—C26—H26 | 119.0 |
C11—C16—H16 | 119.0 | C21—C26—H26 | 119.0 |
C12—O12—C121 | 118.83 (15) | C22—O22—C221 | 117.49 (13) |
O12—C121—H12A | 109.5 | O22—C221—H22A | 109.5 |
O12—C121—H12B | 109.5 | O22—C221—H22B | 109.5 |
H12A—C121—H12B | 109.5 | H22A—C221—H22B | 109.5 |
O12—C121—H12C | 109.5 | O22—C221—H22C | 109.5 |
H12A—C121—H12C | 109.5 | H22A—C221—H22C | 109.5 |
H12B—C121—H12C | 109.5 | H22B—C221—H22C | 109.5 |
C14—O14—C141 | 117.38 (14) | C24—O24—C241 | 117.38 (15) |
O14—C141—H14A | 109.5 | O24—C241—H24A | 109.5 |
O14—C141—H14B | 109.5 | O24—C241—H24B | 109.5 |
H14A—C141—H14B | 109.5 | H24A—C241—H24B | 109.5 |
O14—C141—H14C | 109.5 | O24—C241—H24C | 109.5 |
H14A—C141—H14C | 109.5 | H24A—C241—H24C | 109.5 |
H14B—C141—H14C | 109.5 | H24B—C241—H24C | 109.5 |
C15—O15—C151 | 116.48 (14) | C25—O25—C251 | 116.56 (13) |
O15—C151—H15A | 109.5 | O25—C251—H25A | 109.5 |
O15—C151—H15B | 109.5 | O25—C251—H25B | 109.5 |
H15A—C151—H15B | 109.5 | H25A—C251—H25B | 109.5 |
O15—C151—H15C | 109.5 | O25—C251—H25C | 109.5 |
H15A—C151—H15C | 109.5 | H25A—C251—H25C | 109.5 |
H15B—C151—H15C | 109.5 | H25B—C251—H25C | 109.5 |
| | | |
C2—C1—C11—C12 | 147.9 (2) | C1—C2—C21—C22 | 159.7 (2) |
C2—C1—C11—C16 | −37.5 (3) | C1—C2—C21—C26 | −24.7 (3) |
C16—C11—C12—O12 | −176.60 (15) | C26—C21—C22—O22 | −178.08 (14) |
C1—C11—C12—O12 | −1.8 (2) | C2—C21—C22—O22 | −2.2 (2) |
C16—C11—C12—C13 | 3.0 (2) | C26—C21—C22—C23 | 2.0 (2) |
C1—C11—C12—C13 | 177.80 (16) | C2—C21—C22—C23 | 177.83 (15) |
O12—C12—C13—C14 | 178.13 (16) | O22—C22—C23—C24 | 179.96 (16) |
C11—C12—C13—C14 | −1.4 (3) | C21—C22—C23—C24 | −0.1 (3) |
C12—C13—C14—O14 | 179.83 (16) | C22—C23—C24—O24 | 179.10 (17) |
C12—C13—C14—C15 | −0.3 (3) | C22—C23—C24—C25 | −1.2 (3) |
O14—C14—C15—O15 | 1.1 (2) | O24—C24—C25—O25 | 0.1 (2) |
C13—C14—C15—O15 | −178.75 (15) | C23—C24—C25—O25 | −179.63 (15) |
O14—C14—C15—C16 | −179.75 (14) | O24—C24—C25—C26 | −179.71 (16) |
C13—C14—C15—C16 | 0.4 (2) | C23—C24—C25—C26 | 0.6 (3) |
O15—C15—C16—C11 | −179.67 (15) | O25—C25—C26—C21 | −178.37 (15) |
C14—C15—C16—C11 | 1.3 (2) | C24—C25—C26—C21 | 1.4 (2) |
C12—C11—C16—C15 | −2.9 (2) | C22—C21—C26—C25 | −2.6 (2) |
C1—C11—C16—C15 | −177.59 (15) | C2—C21—C26—C25 | −178.28 (16) |
C13—C12—O12—C121 | 5.4 (3) | C23—C22—O22—C221 | −3.2 (2) |
C11—C12—O12—C121 | −175.05 (16) | C21—C22—O22—C221 | 176.87 (15) |
C13—C14—O14—C141 | −4.2 (3) | C23—C24—O24—C241 | −7.9 (3) |
C15—C14—O14—C141 | 175.94 (15) | C25—C24—O24—C241 | 172.41 (17) |
C16—C15—O15—C151 | 1.6 (2) | C26—C25—O25—C251 | 5.3 (2) |
C14—C15—O15—C151 | −179.30 (15) | C24—C25—O25—C251 | −174.41 (15) |
C11—C1—C2—C21 | −7.8 (4) | | |
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