Molecules of the title compound, C
16H
14O, are chiral and crystallize in space group
P with
Z′ = 2, and with one
R and one
S molecule in the asymmetric unit. The conformations of the phenyl rings in the two independent molecules differ slightly. Supramolecular organization in the crystal is
via tetrameric O—H
H(O) hydrogen-bonded synthons formed separately by each conformer. These tetrameric synthons stack along the
c axis
via C
C—H
O(H) hydrogen bonds. The only link between the conformer stacks is provided by weaker C
methylene—H and C
phenyl—H interactions with π
arene density.
Supporting information
CCDC reference: 153903
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.
1,2-Diphenylbut-3-yn-2-ol
top
Crystal data top
C16H14O | Dx = 1.153 Mg m−3 |
Mr = 222.27 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P4 | Cell parameters from 999 reflections |
Hall symbol: P -4 | θ = 10.2–22.4° |
a = 19.8403 (4) Å | µ = 0.07 mm−1 |
c = 6.5068 (2) Å | T = 150 K |
V = 2561.32 (11) Å3 | Block, colourless |
Z = 8 | 0.4 × 0.3 × 0.3 mm |
F(000) = 944 | |
Data collection top
Bruker SMART CCD diffractometer | 7018 independent reflections |
Radiation source: fine-focus sealed tube | 6166 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: not relevant pixels mm-1 | θmax = 30.4°, θmin = 1.0° |
ω scans | h = −27→23 |
Absorption correction: empirical (using intensity measurements) (XPREP in SHELXL97; Sheldrick, 1997) | k = −27→25 |
Tmin = 0.907, Tmax = 0.979 | l = −9→8 |
20665 measured reflections | |
Refinement top
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: difference Fourier map |
wR(F2) = 0.092 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.057P)2 + 0.1122P] where P = (Fo2 + 2Fc2)/3 |
7018 reflections | (Δ/σ)max = 0.010 |
419 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.20 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. |
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 | 0.21822 (7) | 0.46964 (7) | 0.8364 (3) | 0.0392 (3) | |
H1 | 0.2509 (9) | 0.5052 (9) | 0.900 (3) | 0.041 (4)* | |
C2 | 0.16227 (8) | 0.44983 (8) | 0.9514 (3) | 0.0527 (4) | |
H2 | 0.1552 (11) | 0.4713 (11) | 1.092 (4) | 0.068 (6)* | |
C3 | 0.11804 (8) | 0.40265 (9) | 0.8754 (4) | 0.0603 (6) | |
H3 | 0.0769 (13) | 0.3921 (12) | 0.957 (4) | 0.082 (7)* | |
O17 | 0.41054 (4) | 0.45812 (4) | 0.46004 (12) | 0.02360 (16) | |
H17 | 0.4465 (10) | 0.4396 (10) | 0.490 (3) | 0.050 (5)* | |
C4 | 0.12970 (8) | 0.37424 (9) | 0.6856 (4) | 0.0602 (6) | |
H4 | 0.0965 (13) | 0.3396 (13) | 0.637 (4) | 0.087 (7)* | |
C5 | 0.18615 (7) | 0.39275 (8) | 0.5693 (3) | 0.0438 (4) | |
H5 | 0.1923 (10) | 0.3747 (10) | 0.437 (4) | 0.057 (6)* | |
C6 | 0.23112 (6) | 0.44083 (6) | 0.6444 (2) | 0.0307 (3) | |
C7 | 0.29237 (6) | 0.46152 (6) | 0.5211 (2) | 0.0264 (2) | |
H7A | 0.2855 (8) | 0.4480 (8) | 0.379 (3) | 0.034 (4)* | |
H7B | 0.2982 (7) | 0.5097 (7) | 0.533 (2) | 0.020 (3)* | |
C8 | 0.35937 (5) | 0.42824 (6) | 0.59185 (17) | 0.0217 (2) | |
C9 | 0.35902 (5) | 0.35153 (6) | 0.56278 (19) | 0.0232 (2) | |
C10 | 0.36906 (7) | 0.30716 (6) | 0.7265 (2) | 0.0313 (3) | |
H10 | 0.3740 (8) | 0.3252 (8) | 0.859 (3) | 0.031 (4)* | |
C11 | 0.37064 (9) | 0.23780 (7) | 0.6934 (2) | 0.0409 (3) | |
H11 | 0.3786 (9) | 0.2074 (9) | 0.804 (3) | 0.044 (5)* | |
C12 | 0.36180 (8) | 0.21190 (7) | 0.4967 (3) | 0.0401 (3) | |
H12 | 0.3630 (9) | 0.1620 (9) | 0.475 (3) | 0.048 (5)* | |
C13 | 0.35187 (7) | 0.25563 (7) | 0.3332 (2) | 0.0359 (3) | |
H13 | 0.3452 (9) | 0.2384 (8) | 0.199 (3) | 0.038 (4)* | |
C14 | 0.35057 (7) | 0.32492 (7) | 0.3653 (2) | 0.0308 (3) | |
H14 | 0.3447 (8) | 0.3537 (8) | 0.254 (3) | 0.036 (4)* | |
C15 | 0.37452 (6) | 0.44728 (6) | 0.80705 (18) | 0.0251 (2) | |
C16 | 0.38816 (7) | 0.46420 (7) | 0.9763 (2) | 0.0332 (3) | |
H16 | 0.3986 (8) | 0.4755 (8) | 1.111 (3) | 0.033 (4)* | |
C21 | 0.30482 (7) | −0.00230 (7) | −0.2367 (2) | 0.0358 (3) | |
H21 | 0.2763 (8) | −0.0288 (8) | −0.329 (3) | 0.037 (4)* | |
C22 | 0.36896 (8) | 0.01618 (8) | −0.3045 (3) | 0.0439 (3) | |
H22 | 0.3829 (9) | −0.0001 (9) | −0.441 (3) | 0.046 (5)* | |
C23 | 0.41138 (7) | 0.05300 (8) | −0.1773 (3) | 0.0432 (3) | |
H23 | 0.4542 (10) | 0.0646 (10) | −0.224 (3) | 0.056 (5)* | |
O37 | 0.09534 (4) | 0.01939 (4) | 0.06350 (13) | 0.02451 (17) | |
H37 | 0.0658 (9) | 0.0468 (9) | 0.036 (3) | 0.041 (5)* | |
C24 | 0.38938 (7) | 0.07277 (7) | 0.0143 (3) | 0.0410 (3) | |
H24 | 0.4199 (10) | 0.0993 (10) | 0.100 (3) | 0.055 (5)* | |
C25 | 0.32488 (7) | 0.05526 (7) | 0.0810 (2) | 0.0330 (3) | |
H25 | 0.3062 (9) | 0.0667 (9) | 0.215 (3) | 0.044 (4)* | |
C26 | 0.28189 (6) | 0.01699 (6) | −0.0429 (2) | 0.0262 (2) | |
C27 | 0.21299 (6) | −0.00289 (6) | 0.0347 (2) | 0.0250 (2) | |
H27A | 0.2042 (7) | −0.0497 (8) | 0.007 (2) | 0.027 (3)* | |
H27B | 0.2103 (7) | 0.0006 (7) | 0.185 (2) | 0.027 (4)* | |
C28 | 0.15407 (5) | 0.04001 (6) | −0.05373 (18) | 0.0229 (2) | |
C29 | 0.16810 (5) | 0.11519 (6) | −0.02152 (19) | 0.0245 (2) | |
C30 | 0.18842 (7) | 0.15653 (6) | −0.1831 (2) | 0.0312 (3) | |
H30 | 0.1922 (9) | 0.1366 (9) | −0.319 (3) | 0.045 (5)* | |
C31 | 0.20312 (8) | 0.22435 (7) | −0.1465 (3) | 0.0386 (3) | |
H31 | 0.2179 (8) | 0.2499 (9) | −0.257 (3) | 0.040 (4)* | |
C32 | 0.19832 (7) | 0.25071 (7) | 0.0494 (3) | 0.0393 (3) | |
H32 | 0.2059 (8) | 0.2970 (9) | 0.077 (3) | 0.037 (4)* | |
C33 | 0.17860 (7) | 0.20979 (7) | 0.2112 (2) | 0.0366 (3) | |
H33 | 0.1740 (9) | 0.2274 (9) | 0.356 (3) | 0.042 (4)* | |
C34 | 0.16351 (6) | 0.14189 (6) | 0.1773 (2) | 0.0299 (3) | |
H34 | 0.1491 (7) | 0.1125 (8) | 0.294 (2) | 0.029 (4)* | |
C35 | 0.14079 (6) | 0.02311 (6) | −0.27243 (19) | 0.0261 (2) | |
C36 | 0.12443 (7) | 0.00655 (7) | −0.4409 (2) | 0.0318 (3) | |
H36 | 0.1118 (9) | −0.0026 (9) | −0.570 (3) | 0.045 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0340 (7) | 0.0312 (7) | 0.0525 (9) | 0.0060 (5) | 0.0141 (6) | 0.0047 (6) |
C2 | 0.0443 (8) | 0.0437 (8) | 0.0702 (12) | 0.0154 (7) | 0.0275 (8) | 0.0178 (8) |
C3 | 0.0329 (8) | 0.0475 (9) | 0.1004 (17) | 0.0077 (7) | 0.0215 (9) | 0.0308 (10) |
O17 | 0.0221 (4) | 0.0257 (4) | 0.0230 (4) | −0.0003 (3) | 0.0020 (3) | 0.0021 (3) |
C4 | 0.0280 (7) | 0.0423 (9) | 0.1102 (17) | −0.0083 (6) | −0.0065 (9) | 0.0215 (10) |
C5 | 0.0291 (7) | 0.0355 (7) | 0.0668 (11) | −0.0025 (5) | −0.0086 (7) | 0.0067 (7) |
C6 | 0.0222 (5) | 0.0252 (6) | 0.0447 (7) | 0.0038 (4) | 0.0019 (5) | 0.0075 (5) |
C7 | 0.0236 (5) | 0.0258 (5) | 0.0296 (6) | 0.0016 (4) | −0.0008 (4) | 0.0023 (5) |
C8 | 0.0214 (5) | 0.0232 (5) | 0.0207 (5) | −0.0006 (4) | 0.0012 (4) | 0.0005 (4) |
C9 | 0.0198 (5) | 0.0236 (5) | 0.0264 (6) | −0.0007 (4) | 0.0015 (4) | −0.0015 (4) |
C10 | 0.0406 (7) | 0.0261 (6) | 0.0271 (6) | 0.0000 (5) | 0.0073 (5) | 0.0017 (5) |
C11 | 0.0539 (9) | 0.0265 (6) | 0.0422 (8) | −0.0010 (6) | 0.0120 (7) | 0.0068 (6) |
C12 | 0.0408 (7) | 0.0254 (6) | 0.0541 (9) | −0.0048 (5) | 0.0095 (6) | −0.0056 (6) |
C13 | 0.0349 (7) | 0.0346 (7) | 0.0382 (7) | −0.0019 (5) | −0.0024 (5) | −0.0114 (6) |
C14 | 0.0314 (6) | 0.0308 (6) | 0.0301 (6) | 0.0002 (5) | −0.0044 (5) | −0.0037 (5) |
C15 | 0.0256 (5) | 0.0240 (5) | 0.0257 (6) | −0.0004 (4) | 0.0019 (4) | 0.0015 (4) |
C16 | 0.0415 (7) | 0.0335 (6) | 0.0245 (6) | −0.0030 (5) | −0.0003 (5) | −0.0015 (5) |
C21 | 0.0306 (6) | 0.0382 (7) | 0.0386 (7) | −0.0012 (5) | −0.0003 (5) | −0.0042 (6) |
C22 | 0.0372 (7) | 0.0466 (8) | 0.0479 (9) | −0.0009 (6) | 0.0110 (6) | −0.0019 (7) |
C23 | 0.0289 (7) | 0.0375 (7) | 0.0632 (10) | −0.0042 (5) | 0.0063 (7) | 0.0010 (7) |
O37 | 0.0225 (4) | 0.0249 (4) | 0.0262 (4) | 0.0007 (3) | 0.0004 (3) | 0.0019 (3) |
C24 | 0.0302 (6) | 0.0339 (7) | 0.0588 (10) | −0.0060 (5) | −0.0054 (6) | −0.0029 (6) |
C25 | 0.0297 (6) | 0.0298 (6) | 0.0395 (7) | −0.0001 (5) | −0.0036 (5) | −0.0020 (5) |
C26 | 0.0236 (5) | 0.0222 (5) | 0.0327 (6) | 0.0027 (4) | −0.0030 (5) | 0.0031 (5) |
C27 | 0.0236 (5) | 0.0233 (5) | 0.0280 (6) | 0.0009 (4) | −0.0019 (4) | 0.0032 (4) |
C28 | 0.0222 (5) | 0.0230 (5) | 0.0234 (5) | −0.0004 (4) | −0.0003 (4) | 0.0008 (4) |
C29 | 0.0202 (5) | 0.0233 (5) | 0.0300 (6) | 0.0012 (4) | −0.0034 (4) | 0.0010 (4) |
C30 | 0.0323 (6) | 0.0276 (6) | 0.0336 (7) | −0.0014 (5) | −0.0009 (5) | 0.0034 (5) |
C31 | 0.0389 (7) | 0.0280 (6) | 0.0490 (8) | −0.0048 (5) | −0.0035 (6) | 0.0097 (6) |
C32 | 0.0378 (7) | 0.0230 (6) | 0.0572 (9) | −0.0029 (5) | −0.0124 (6) | −0.0001 (6) |
C33 | 0.0376 (7) | 0.0317 (7) | 0.0404 (7) | 0.0016 (5) | −0.0103 (6) | −0.0077 (6) |
C34 | 0.0292 (6) | 0.0277 (6) | 0.0328 (7) | 0.0010 (5) | −0.0044 (5) | −0.0010 (5) |
C35 | 0.0251 (5) | 0.0248 (5) | 0.0283 (6) | −0.0012 (4) | 0.0002 (4) | 0.0018 (4) |
C36 | 0.0349 (6) | 0.0350 (6) | 0.0256 (6) | −0.0037 (5) | −0.0012 (5) | 0.0005 (5) |
Geometric parameters (Å, º) top
C1—C2 | 1.395 (2) | C21—C26 | 1.394 (2) |
C1—C6 | 1.398 (2) | C21—C22 | 1.396 (2) |
C1—H1 | 1.044 (18) | C21—H21 | 0.977 (17) |
C2—C3 | 1.375 (3) | C22—C23 | 1.388 (2) |
C2—H2 | 1.02 (2) | C22—H22 | 0.98 (2) |
C3—C4 | 1.377 (3) | C23—C24 | 1.378 (2) |
C3—H3 | 1.00 (3) | C23—H23 | 0.93 (2) |
O17—C8 | 1.4552 (13) | O37—C28 | 1.4516 (14) |
O17—H17 | 0.83 (2) | O37—H37 | 0.820 (18) |
C4—C5 | 1.401 (3) | C24—C25 | 1.395 (2) |
C4—H4 | 1.00 (3) | C24—H24 | 0.98 (2) |
C5—C6 | 1.394 (2) | C25—C26 | 1.3978 (18) |
C5—H5 | 0.94 (2) | C25—H25 | 0.974 (19) |
C6—C7 | 1.5129 (17) | C26—C27 | 1.5100 (16) |
C7—C8 | 1.5539 (16) | C27—C28 | 1.5564 (16) |
C7—H7A | 0.975 (17) | C27—H27A | 0.961 (15) |
C7—H7B | 0.966 (14) | C27—H27B | 0.979 (15) |
C8—C15 | 1.4812 (16) | C28—C35 | 1.4856 (17) |
C8—C9 | 1.5337 (16) | C28—C29 | 1.5318 (16) |
C9—C10 | 1.3964 (17) | C29—C30 | 1.3931 (18) |
C9—C14 | 1.3995 (18) | C29—C34 | 1.4007 (18) |
C10—C11 | 1.3931 (19) | C30—C31 | 1.3971 (19) |
C10—H10 | 0.941 (18) | C30—H30 | 0.97 (2) |
C11—C12 | 1.390 (2) | C31—C32 | 1.382 (2) |
C11—H11 | 0.950 (19) | C31—H31 | 0.930 (19) |
C12—C13 | 1.387 (2) | C32—C33 | 1.385 (2) |
C12—H12 | 1.000 (18) | C32—H32 | 0.948 (17) |
C13—C14 | 1.3907 (19) | C33—C34 | 1.3976 (19) |
C13—H13 | 0.950 (18) | C33—H33 | 1.01 (2) |
C14—H14 | 0.931 (18) | C34—H34 | 0.998 (16) |
C15—C16 | 1.1828 (18) | C35—C36 | 1.1893 (18) |
C16—H16 | 0.926 (17) | C36—H36 | 0.90 (2) |
| | | |
C2—C1—C6 | 120.67 (16) | C26—C21—C22 | 120.74 (13) |
C2—C1—H1 | 118.0 (10) | C26—C21—H21 | 120.9 (10) |
C6—C1—H1 | 121.3 (10) | C22—C21—H21 | 118.4 (10) |
C3—C2—C1 | 120.43 (19) | C23—C22—C21 | 120.17 (15) |
C3—C2—H2 | 121.3 (13) | C23—C22—H22 | 122.6 (10) |
C1—C2—H2 | 118.3 (13) | C21—C22—H22 | 117.1 (10) |
C2—C3—C4 | 119.59 (16) | C24—C23—C22 | 119.81 (14) |
C2—C3—H3 | 118.3 (14) | C24—C23—H23 | 120.8 (13) |
C4—C3—H3 | 122.0 (14) | C22—C23—H23 | 119.4 (13) |
C8—O17—H17 | 106.5 (14) | C28—O37—H37 | 105.7 (12) |
C3—C4—C5 | 120.76 (18) | C23—C24—C25 | 120.06 (14) |
C3—C4—H4 | 116.9 (15) | C23—C24—H24 | 118.2 (12) |
C5—C4—H4 | 122.4 (15) | C25—C24—H24 | 121.7 (12) |
C6—C5—C4 | 120.13 (19) | C24—C25—C26 | 121.03 (14) |
C6—C5—H5 | 119.8 (13) | C24—C25—H25 | 124.6 (11) |
C4—C5—H5 | 119.9 (13) | C26—C25—H25 | 114.3 (11) |
C5—C6—C1 | 118.40 (13) | C21—C26—C25 | 118.15 (12) |
C5—C6—C7 | 120.93 (14) | C21—C26—C27 | 121.76 (11) |
C1—C6—C7 | 120.66 (12) | C25—C26—C27 | 120.09 (12) |
C6—C7—C8 | 114.50 (10) | C26—C27—C28 | 114.42 (9) |
C6—C7—H7A | 108.5 (10) | C26—C27—H27A | 110.8 (9) |
C8—C7—H7A | 106.5 (10) | C28—C27—H27A | 108.8 (9) |
C6—C7—H7B | 108.8 (8) | C26—C27—H27B | 111.4 (8) |
C8—C7—H7B | 107.1 (8) | C28—C27—H27B | 106.8 (9) |
H7A—C7—H7B | 111.4 (12) | H27A—C27—H27B | 104.1 (13) |
O17—C8—C15 | 108.16 (9) | O37—C28—C35 | 107.30 (9) |
O17—C8—C9 | 109.55 (9) | O37—C28—C29 | 110.39 (9) |
C15—C8—C9 | 111.75 (9) | C35—C28—C29 | 112.52 (10) |
O17—C8—C7 | 104.42 (9) | O37—C28—C27 | 104.74 (9) |
C15—C8—C7 | 110.21 (9) | C35—C28—C27 | 111.35 (10) |
C9—C8—C7 | 112.41 (9) | C29—C28—C27 | 110.21 (9) |
C10—C9—C14 | 118.67 (11) | C30—C29—C34 | 119.55 (11) |
C10—C9—C8 | 122.07 (11) | C30—C29—C28 | 121.51 (11) |
C14—C9—C8 | 119.22 (10) | C34—C29—C28 | 118.86 (10) |
C11—C10—C9 | 120.52 (13) | C29—C30—C31 | 119.93 (13) |
C11—C10—H10 | 121.0 (9) | C29—C30—H30 | 118.1 (11) |
C9—C10—H10 | 118.5 (9) | C31—C30—H30 | 122.0 (11) |
C12—C11—C10 | 120.31 (14) | C32—C31—C30 | 120.48 (14) |
C12—C11—H11 | 118.7 (11) | C32—C31—H31 | 122.1 (11) |
C10—C11—H11 | 120.9 (11) | C30—C31—H31 | 117.4 (11) |
C13—C12—C11 | 119.53 (12) | C31—C32—C33 | 119.92 (12) |
C13—C12—H12 | 120.9 (11) | C31—C32—H32 | 122.1 (10) |
C11—C12—H12 | 119.5 (11) | C33—C32—H32 | 117.9 (10) |
C12—C13—C14 | 120.38 (13) | C32—C33—C34 | 120.36 (14) |
C12—C13—H13 | 120.1 (10) | C32—C33—H33 | 122.1 (10) |
C14—C13—H13 | 119.5 (10) | C34—C33—H33 | 117.5 (10) |
C13—C14—C9 | 120.58 (13) | C33—C34—C29 | 119.76 (13) |
C13—C14—H14 | 119.4 (11) | C33—C34—H34 | 120.4 (9) |
C9—C14—H14 | 120.0 (11) | C29—C34—H34 | 119.9 (9) |
C16—C15—C8 | 177.64 (13) | C36—C35—C28 | 173.46 (13) |
C15—C16—H16 | 177.4 (10) | C35—C36—H36 | 175.6 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O17i | 0.93 (2) | 2.31 (2) | 3.181 (2) | 156 (1) |
C36—H36···O37ii | 0.90 (2) | 2.44 (2) | 3.2862 (16) | 156 (2) |
O37—H37···O37iii | 0.82 (2) | 2.05 (2) | 2.852 (1) | 166 (2) |
O17—H17···O17iv | 0.83 (2) | 2.00 (2) | 2.8200 (12) | 169 (2) |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) −y, x, −z; (iv) −y+1, x, −z+1. |