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Molecules of the title compound, C16H14O, are chiral and crystallize in space group P\overline 4 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[triple bond]C—H...O(H) hydrogen bonds. The only link between the conformer stacks is provided by weaker Cmethylene—H and Cphenyl—H interactions with πarene density.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011343/gd1108sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011343/gd1108Isup2.hkl
Contains datablock I

CCDC reference: 153903

Computing details top

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
C16H14ODx = 1.153 Mg m3
Mr = 222.27Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4Cell parameters from 999 reflections
Hall symbol: P -4θ = 10.2–22.4°
a = 19.8403 (4) ŵ = 0.07 mm1
c = 6.5068 (2) ÅT = 150 K
V = 2561.32 (11) Å3Block, colourless
Z = 80.4 × 0.3 × 0.3 mm
F(000) = 944
Data collection top
Bruker SMART CCD
diffractometer
7018 independent reflections
Radiation source: fine-focus sealed tube6166 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: not relevant pixels mm-1θmax = 30.4°, θmin = 1.0°
ω scansh = 2723
Absorption correction: empirical (using intensity measurements)
(XPREP in SHELXL97; Sheldrick, 1997)
k = 2725
Tmin = 0.907, Tmax = 0.979l = 98
20665 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: difference Fourier map
wR(F2) = 0.092All 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 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
C10.21822 (7)0.46964 (7)0.8364 (3)0.0392 (3)
H10.2509 (9)0.5052 (9)0.900 (3)0.041 (4)*
C20.16227 (8)0.44983 (8)0.9514 (3)0.0527 (4)
H20.1552 (11)0.4713 (11)1.092 (4)0.068 (6)*
C30.11804 (8)0.40265 (9)0.8754 (4)0.0603 (6)
H30.0769 (13)0.3921 (12)0.957 (4)0.082 (7)*
O170.41054 (4)0.45812 (4)0.46004 (12)0.02360 (16)
H170.4465 (10)0.4396 (10)0.490 (3)0.050 (5)*
C40.12970 (8)0.37424 (9)0.6856 (4)0.0602 (6)
H40.0965 (13)0.3396 (13)0.637 (4)0.087 (7)*
C50.18615 (7)0.39275 (8)0.5693 (3)0.0438 (4)
H50.1923 (10)0.3747 (10)0.437 (4)0.057 (6)*
C60.23112 (6)0.44083 (6)0.6444 (2)0.0307 (3)
C70.29237 (6)0.46152 (6)0.5211 (2)0.0264 (2)
H7A0.2855 (8)0.4480 (8)0.379 (3)0.034 (4)*
H7B0.2982 (7)0.5097 (7)0.533 (2)0.020 (3)*
C80.35937 (5)0.42824 (6)0.59185 (17)0.0217 (2)
C90.35902 (5)0.35153 (6)0.56278 (19)0.0232 (2)
C100.36906 (7)0.30716 (6)0.7265 (2)0.0313 (3)
H100.3740 (8)0.3252 (8)0.859 (3)0.031 (4)*
C110.37064 (9)0.23780 (7)0.6934 (2)0.0409 (3)
H110.3786 (9)0.2074 (9)0.804 (3)0.044 (5)*
C120.36180 (8)0.21190 (7)0.4967 (3)0.0401 (3)
H120.3630 (9)0.1620 (9)0.475 (3)0.048 (5)*
C130.35187 (7)0.25563 (7)0.3332 (2)0.0359 (3)
H130.3452 (9)0.2384 (8)0.199 (3)0.038 (4)*
C140.35057 (7)0.32492 (7)0.3653 (2)0.0308 (3)
H140.3447 (8)0.3537 (8)0.254 (3)0.036 (4)*
C150.37452 (6)0.44728 (6)0.80705 (18)0.0251 (2)
C160.38816 (7)0.46420 (7)0.9763 (2)0.0332 (3)
H160.3986 (8)0.4755 (8)1.111 (3)0.033 (4)*
C210.30482 (7)0.00230 (7)0.2367 (2)0.0358 (3)
H210.2763 (8)0.0288 (8)0.329 (3)0.037 (4)*
C220.36896 (8)0.01618 (8)0.3045 (3)0.0439 (3)
H220.3829 (9)0.0001 (9)0.441 (3)0.046 (5)*
C230.41138 (7)0.05300 (8)0.1773 (3)0.0432 (3)
H230.4542 (10)0.0646 (10)0.224 (3)0.056 (5)*
O370.09534 (4)0.01939 (4)0.06350 (13)0.02451 (17)
H370.0658 (9)0.0468 (9)0.036 (3)0.041 (5)*
C240.38938 (7)0.07277 (7)0.0143 (3)0.0410 (3)
H240.4199 (10)0.0993 (10)0.100 (3)0.055 (5)*
C250.32488 (7)0.05526 (7)0.0810 (2)0.0330 (3)
H250.3062 (9)0.0667 (9)0.215 (3)0.044 (4)*
C260.28189 (6)0.01699 (6)0.0429 (2)0.0262 (2)
C270.21299 (6)0.00289 (6)0.0347 (2)0.0250 (2)
H27A0.2042 (7)0.0497 (8)0.007 (2)0.027 (3)*
H27B0.2103 (7)0.0006 (7)0.185 (2)0.027 (4)*
C280.15407 (5)0.04001 (6)0.05373 (18)0.0229 (2)
C290.16810 (5)0.11519 (6)0.02152 (19)0.0245 (2)
C300.18842 (7)0.15653 (6)0.1831 (2)0.0312 (3)
H300.1922 (9)0.1366 (9)0.319 (3)0.045 (5)*
C310.20312 (8)0.22435 (7)0.1465 (3)0.0386 (3)
H310.2179 (8)0.2499 (9)0.257 (3)0.040 (4)*
C320.19832 (7)0.25071 (7)0.0494 (3)0.0393 (3)
H320.2059 (8)0.2970 (9)0.077 (3)0.037 (4)*
C330.17860 (7)0.20979 (7)0.2112 (2)0.0366 (3)
H330.1740 (9)0.2274 (9)0.356 (3)0.042 (4)*
C340.16351 (6)0.14189 (6)0.1773 (2)0.0299 (3)
H340.1491 (7)0.1125 (8)0.294 (2)0.029 (4)*
C350.14079 (6)0.02311 (6)0.27243 (19)0.0261 (2)
C360.12443 (7)0.00655 (7)0.4409 (2)0.0318 (3)
H360.1118 (9)0.0026 (9)0.570 (3)0.045 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0340 (7)0.0312 (7)0.0525 (9)0.0060 (5)0.0141 (6)0.0047 (6)
C20.0443 (8)0.0437 (8)0.0702 (12)0.0154 (7)0.0275 (8)0.0178 (8)
C30.0329 (8)0.0475 (9)0.1004 (17)0.0077 (7)0.0215 (9)0.0308 (10)
O170.0221 (4)0.0257 (4)0.0230 (4)0.0003 (3)0.0020 (3)0.0021 (3)
C40.0280 (7)0.0423 (9)0.1102 (17)0.0083 (6)0.0065 (9)0.0215 (10)
C50.0291 (7)0.0355 (7)0.0668 (11)0.0025 (5)0.0086 (7)0.0067 (7)
C60.0222 (5)0.0252 (6)0.0447 (7)0.0038 (4)0.0019 (5)0.0075 (5)
C70.0236 (5)0.0258 (5)0.0296 (6)0.0016 (4)0.0008 (4)0.0023 (5)
C80.0214 (5)0.0232 (5)0.0207 (5)0.0006 (4)0.0012 (4)0.0005 (4)
C90.0198 (5)0.0236 (5)0.0264 (6)0.0007 (4)0.0015 (4)0.0015 (4)
C100.0406 (7)0.0261 (6)0.0271 (6)0.0000 (5)0.0073 (5)0.0017 (5)
C110.0539 (9)0.0265 (6)0.0422 (8)0.0010 (6)0.0120 (7)0.0068 (6)
C120.0408 (7)0.0254 (6)0.0541 (9)0.0048 (5)0.0095 (6)0.0056 (6)
C130.0349 (7)0.0346 (7)0.0382 (7)0.0019 (5)0.0024 (5)0.0114 (6)
C140.0314 (6)0.0308 (6)0.0301 (6)0.0002 (5)0.0044 (5)0.0037 (5)
C150.0256 (5)0.0240 (5)0.0257 (6)0.0004 (4)0.0019 (4)0.0015 (4)
C160.0415 (7)0.0335 (6)0.0245 (6)0.0030 (5)0.0003 (5)0.0015 (5)
C210.0306 (6)0.0382 (7)0.0386 (7)0.0012 (5)0.0003 (5)0.0042 (6)
C220.0372 (7)0.0466 (8)0.0479 (9)0.0009 (6)0.0110 (6)0.0019 (7)
C230.0289 (7)0.0375 (7)0.0632 (10)0.0042 (5)0.0063 (7)0.0010 (7)
O370.0225 (4)0.0249 (4)0.0262 (4)0.0007 (3)0.0004 (3)0.0019 (3)
C240.0302 (6)0.0339 (7)0.0588 (10)0.0060 (5)0.0054 (6)0.0029 (6)
C250.0297 (6)0.0298 (6)0.0395 (7)0.0001 (5)0.0036 (5)0.0020 (5)
C260.0236 (5)0.0222 (5)0.0327 (6)0.0027 (4)0.0030 (5)0.0031 (5)
C270.0236 (5)0.0233 (5)0.0280 (6)0.0009 (4)0.0019 (4)0.0032 (4)
C280.0222 (5)0.0230 (5)0.0234 (5)0.0004 (4)0.0003 (4)0.0008 (4)
C290.0202 (5)0.0233 (5)0.0300 (6)0.0012 (4)0.0034 (4)0.0010 (4)
C300.0323 (6)0.0276 (6)0.0336 (7)0.0014 (5)0.0009 (5)0.0034 (5)
C310.0389 (7)0.0280 (6)0.0490 (8)0.0048 (5)0.0035 (6)0.0097 (6)
C320.0378 (7)0.0230 (6)0.0572 (9)0.0029 (5)0.0124 (6)0.0001 (6)
C330.0376 (7)0.0317 (7)0.0404 (7)0.0016 (5)0.0103 (6)0.0077 (6)
C340.0292 (6)0.0277 (6)0.0328 (7)0.0010 (5)0.0044 (5)0.0010 (5)
C350.0251 (5)0.0248 (5)0.0283 (6)0.0012 (4)0.0002 (4)0.0018 (4)
C360.0349 (6)0.0350 (6)0.0256 (6)0.0037 (5)0.0012 (5)0.0005 (5)
Geometric parameters (Å, º) top
C1—C21.395 (2)C21—C261.394 (2)
C1—C61.398 (2)C21—C221.396 (2)
C1—H11.044 (18)C21—H210.977 (17)
C2—C31.375 (3)C22—C231.388 (2)
C2—H21.02 (2)C22—H220.98 (2)
C3—C41.377 (3)C23—C241.378 (2)
C3—H31.00 (3)C23—H230.93 (2)
O17—C81.4552 (13)O37—C281.4516 (14)
O17—H170.83 (2)O37—H370.820 (18)
C4—C51.401 (3)C24—C251.395 (2)
C4—H41.00 (3)C24—H240.98 (2)
C5—C61.394 (2)C25—C261.3978 (18)
C5—H50.94 (2)C25—H250.974 (19)
C6—C71.5129 (17)C26—C271.5100 (16)
C7—C81.5539 (16)C27—C281.5564 (16)
C7—H7A0.975 (17)C27—H27A0.961 (15)
C7—H7B0.966 (14)C27—H27B0.979 (15)
C8—C151.4812 (16)C28—C351.4856 (17)
C8—C91.5337 (16)C28—C291.5318 (16)
C9—C101.3964 (17)C29—C301.3931 (18)
C9—C141.3995 (18)C29—C341.4007 (18)
C10—C111.3931 (19)C30—C311.3971 (19)
C10—H100.941 (18)C30—H300.97 (2)
C11—C121.390 (2)C31—C321.382 (2)
C11—H110.950 (19)C31—H310.930 (19)
C12—C131.387 (2)C32—C331.385 (2)
C12—H121.000 (18)C32—H320.948 (17)
C13—C141.3907 (19)C33—C341.3976 (19)
C13—H130.950 (18)C33—H331.01 (2)
C14—H140.931 (18)C34—H340.998 (16)
C15—C161.1828 (18)C35—C361.1893 (18)
C16—H160.926 (17)C36—H360.90 (2)
C2—C1—C6120.67 (16)C26—C21—C22120.74 (13)
C2—C1—H1118.0 (10)C26—C21—H21120.9 (10)
C6—C1—H1121.3 (10)C22—C21—H21118.4 (10)
C3—C2—C1120.43 (19)C23—C22—C21120.17 (15)
C3—C2—H2121.3 (13)C23—C22—H22122.6 (10)
C1—C2—H2118.3 (13)C21—C22—H22117.1 (10)
C2—C3—C4119.59 (16)C24—C23—C22119.81 (14)
C2—C3—H3118.3 (14)C24—C23—H23120.8 (13)
C4—C3—H3122.0 (14)C22—C23—H23119.4 (13)
C8—O17—H17106.5 (14)C28—O37—H37105.7 (12)
C3—C4—C5120.76 (18)C23—C24—C25120.06 (14)
C3—C4—H4116.9 (15)C23—C24—H24118.2 (12)
C5—C4—H4122.4 (15)C25—C24—H24121.7 (12)
C6—C5—C4120.13 (19)C24—C25—C26121.03 (14)
C6—C5—H5119.8 (13)C24—C25—H25124.6 (11)
C4—C5—H5119.9 (13)C26—C25—H25114.3 (11)
C5—C6—C1118.40 (13)C21—C26—C25118.15 (12)
C5—C6—C7120.93 (14)C21—C26—C27121.76 (11)
C1—C6—C7120.66 (12)C25—C26—C27120.09 (12)
C6—C7—C8114.50 (10)C26—C27—C28114.42 (9)
C6—C7—H7A108.5 (10)C26—C27—H27A110.8 (9)
C8—C7—H7A106.5 (10)C28—C27—H27A108.8 (9)
C6—C7—H7B108.8 (8)C26—C27—H27B111.4 (8)
C8—C7—H7B107.1 (8)C28—C27—H27B106.8 (9)
H7A—C7—H7B111.4 (12)H27A—C27—H27B104.1 (13)
O17—C8—C15108.16 (9)O37—C28—C35107.30 (9)
O17—C8—C9109.55 (9)O37—C28—C29110.39 (9)
C15—C8—C9111.75 (9)C35—C28—C29112.52 (10)
O17—C8—C7104.42 (9)O37—C28—C27104.74 (9)
C15—C8—C7110.21 (9)C35—C28—C27111.35 (10)
C9—C8—C7112.41 (9)C29—C28—C27110.21 (9)
C10—C9—C14118.67 (11)C30—C29—C34119.55 (11)
C10—C9—C8122.07 (11)C30—C29—C28121.51 (11)
C14—C9—C8119.22 (10)C34—C29—C28118.86 (10)
C11—C10—C9120.52 (13)C29—C30—C31119.93 (13)
C11—C10—H10121.0 (9)C29—C30—H30118.1 (11)
C9—C10—H10118.5 (9)C31—C30—H30122.0 (11)
C12—C11—C10120.31 (14)C32—C31—C30120.48 (14)
C12—C11—H11118.7 (11)C32—C31—H31122.1 (11)
C10—C11—H11120.9 (11)C30—C31—H31117.4 (11)
C13—C12—C11119.53 (12)C31—C32—C33119.92 (12)
C13—C12—H12120.9 (11)C31—C32—H32122.1 (10)
C11—C12—H12119.5 (11)C33—C32—H32117.9 (10)
C12—C13—C14120.38 (13)C32—C33—C34120.36 (14)
C12—C13—H13120.1 (10)C32—C33—H33122.1 (10)
C14—C13—H13119.5 (10)C34—C33—H33117.5 (10)
C13—C14—C9120.58 (13)C33—C34—C29119.76 (13)
C13—C14—H14119.4 (11)C33—C34—H34120.4 (9)
C9—C14—H14120.0 (11)C29—C34—H34119.9 (9)
C16—C15—C8177.64 (13)C36—C35—C28173.46 (13)
C15—C16—H16177.4 (10)C35—C36—H36175.6 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O17i0.93 (2)2.31 (2)3.181 (2)156 (1)
C36—H36···O37ii0.90 (2)2.44 (2)3.2862 (16)156 (2)
O37—H37···O37iii0.82 (2)2.05 (2)2.852 (1)166 (2)
O17—H17···O17iv0.83 (2)2.00 (2)2.8200 (12)169 (2)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z1; (iii) y, x, z; (iv) y+1, x, z+1.
 

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