Homopropargyl alcohol 5,5-di­phenyl­pent-2-yne-1,5-diol

In the title compound, C₁₇H₁₆O₂, the central carbon atom has a distorted tetra­hedral geometry [spread of angles = 105.71 (8)–112.75 (9)°] for its bonds to a homopropargylic but-2-yn-1-ol moiety, a hy­droxy group and two phenyl substituents. In the crystal, O—H...O hydrogen-bonding inter­actions link the mol­ecules into [001] chains and C—H...π(ring) contacts consolidate the packing.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.104
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1       ..H2'      .       2.12 Ang.
                                                    x,y,1+z  =      1_556 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.480 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.139 Check

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2015); cell refinement: APEX3 (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

5,5-Diphenylpent-2-yne-1,5-diol

Crystal data

C17H16O2	F(000) = 536
Mr = 252.30	Dx = 1.259 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.9772 (3) Å	Cell parameters from 117 reflections
b = 22.8528 (8) Å	θ = 3.6–23.1°
c = 7.3075 (3) Å	µ = 0.08 mm^−1
β = 92.791 (1)°	T = 100 K
V = 1330.59 (9) Å^3	Block, colourless
Z = 4	0.50 × 0.34 × 0.25 mm

Data collection

Bruker D8 Venture diffractometer	3060 independent reflections
Radiation source: Incoatec Microsource	2668 reflections with I > 2σ(I)
Mirrors monochromator	Rint = 0.050
Detector resolution: 10.4167 pixels mm^-1	θmax = 27.5°, θmin = 2.6°
ω scans	h = −8→10
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −29→29
Tmin = 0.727, Tmax = 0.746	l = −9→9
65030 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.053P)^2 + 0.6384P] where P = (Fo^2 + 2Fc^2)/3
3060 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.27538 (10)	0.54181 (3)	0.43375 (11)	0.01258 (19)
H1	0.345 (2)	0.5263 (5)	0.3615 (17)	0.019*
O2	0.46943 (11)	0.51425 (4)	−0.26458 (12)	0.0171 (2)
H2'	0.4133 (13)	0.5299 (7)	−0.355 (2)	0.026*
C1	0.34385 (14)	0.63310 (5)	0.28443 (15)	0.0115 (2)
C2	0.33084 (15)	0.66221 (5)	0.11643 (17)	0.0159 (2)
H2	0.2316	0.6583	0.0402	0.019*
C3	0.46201 (17)	0.69690 (6)	0.05955 (18)	0.0206 (3)
H3	0.4515	0.7166	−0.0549	0.025*
C4	0.60738 (17)	0.70284 (5)	0.16880 (18)	0.0202 (3)
H4	0.6968	0.7264	0.1294	0.024*
C5	0.62206 (15)	0.67418 (5)	0.33639 (18)	0.0178 (3)
H5	0.722	0.678	0.4116	0.021*
C6	0.49087 (15)	0.63986 (5)	0.39436 (16)	0.0149 (2)
H6	0.5013	0.6208	0.5099	0.018*
C7	0.20382 (14)	0.59370 (5)	0.35016 (15)	0.0104 (2)
C8	0.10203 (14)	0.62267 (5)	0.49755 (15)	0.0117 (2)
C9	−0.01385 (15)	0.58905 (5)	0.58940 (17)	0.0159 (2)
H9	−0.0277	0.5488	0.5593	0.019*
C10	−0.10905 (16)	0.61360 (6)	0.72402 (17)	0.0196 (3)
H10	−0.1869	0.5902	0.7857	0.024*
C11	−0.09031 (16)	0.67244 (6)	0.76825 (17)	0.0201 (3)
H11	−0.1553	0.6893	0.8601	0.024*
C12	0.02357 (16)	0.70637 (6)	0.67798 (17)	0.0192 (3)
H12	0.0364	0.7466	0.7079	0.023*
C13	0.11950 (15)	0.68163 (5)	0.54327 (16)	0.0150 (2)
H13	0.1974	0.7052	0.4822	0.018*
C14	0.08274 (14)	0.57347 (5)	0.19017 (15)	0.0127 (2)
H14A	−0.0068	0.5488	0.2391	0.015*
H14B	0.0291	0.6081	0.1309	0.015*
C15	0.17153 (14)	0.54009 (5)	0.05346 (16)	0.0127 (2)
C16	0.25424 (14)	0.51196 (5)	−0.04534 (16)	0.0138 (2)
C17	0.36115 (15)	0.47781 (5)	−0.16380 (16)	0.0153 (2)
H17A	0.43	0.4502	−0.0875	0.018*
H17B	0.2892	0.4545	−0.2507	0.018*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0132 (4)	0.0123 (4)	0.0125 (4)	0.0038 (3)	0.0025 (3)	0.0022 (3)
O2	0.0142 (4)	0.0248 (5)	0.0124 (4)	0.0041 (3)	0.0021 (3)	0.0033 (3)
C1	0.0112 (5)	0.0105 (5)	0.0130 (5)	0.0007 (4)	0.0032 (4)	−0.0014 (4)
C2	0.0163 (6)	0.0165 (5)	0.0149 (6)	−0.0008 (4)	0.0010 (4)	0.0016 (4)
C3	0.0261 (7)	0.0181 (6)	0.0183 (6)	−0.0035 (5)	0.0070 (5)	0.0029 (5)
C4	0.0191 (6)	0.0173 (6)	0.0252 (7)	−0.0058 (5)	0.0109 (5)	−0.0044 (5)
C5	0.0122 (5)	0.0179 (6)	0.0234 (6)	−0.0019 (4)	0.0021 (5)	−0.0071 (5)
C6	0.0147 (5)	0.0148 (5)	0.0152 (6)	0.0004 (4)	0.0006 (4)	−0.0018 (4)
C7	0.0101 (5)	0.0108 (5)	0.0102 (5)	0.0009 (4)	0.0008 (4)	0.0013 (4)
C8	0.0107 (5)	0.0150 (5)	0.0095 (5)	0.0031 (4)	−0.0004 (4)	0.0004 (4)
C9	0.0174 (6)	0.0148 (5)	0.0160 (6)	0.0029 (4)	0.0043 (4)	0.0030 (4)
C10	0.0201 (6)	0.0240 (6)	0.0154 (6)	0.0057 (5)	0.0067 (5)	0.0054 (5)
C11	0.0211 (6)	0.0272 (6)	0.0122 (5)	0.0094 (5)	0.0034 (5)	−0.0015 (5)
C12	0.0212 (6)	0.0183 (6)	0.0180 (6)	0.0042 (5)	−0.0004 (5)	−0.0057 (5)
C13	0.0139 (5)	0.0160 (5)	0.0151 (6)	0.0010 (4)	0.0005 (4)	−0.0014 (4)
C14	0.0103 (5)	0.0156 (5)	0.0122 (5)	−0.0006 (4)	0.0009 (4)	−0.0013 (4)
C15	0.0108 (5)	0.0153 (5)	0.0118 (5)	−0.0017 (4)	−0.0016 (4)	0.0000 (4)
C16	0.0116 (5)	0.0170 (5)	0.0126 (5)	−0.0015 (4)	−0.0015 (4)	−0.0002 (4)
C17	0.0134 (5)	0.0173 (5)	0.0151 (6)	0.0006 (4)	0.0009 (4)	−0.0029 (4)

Geometric parameters (Å, º)

O1—C7	1.4391 (13)	C8—C13	1.3936 (16)
O1—H1	0.860 (17)	C8—C9	1.3985 (16)
O2—C17	1.4296 (14)	C9—C10	1.3900 (16)
O2—H2'	0.857 (18)	C9—H9	0.95
C1—C2	1.3957 (16)	C10—C11	1.3892 (19)
C1—C6	1.3974 (16)	C10—H10	0.95
C1—C7	1.5302 (15)	C11—C12	1.3856 (19)
C2—C3	1.3923 (17)	C11—H11	0.95
C2—H2	0.95	C12—C13	1.3956 (16)
C3—C4	1.3822 (19)	C12—H12	0.95
C3—H3	0.95	C13—H13	0.95
C4—C5	1.3888 (19)	C14—C15	1.4665 (15)
C4—H4	0.95	C14—H14A	0.99
C5—C6	1.3903 (16)	C14—H14B	0.99
C5—H5	0.95	C15—C16	1.1900 (17)
C6—H6	0.95	C16—C17	1.4690 (16)
C7—C8	1.5307 (15)	C17—H17A	0.99
C7—C14	1.5503 (15)	C17—H17B	0.99
C7—O1—H1	109.5	C10—C9—C8	120.97 (11)
C17—O2—H2'	109.5	C10—C9—H9	119.5
C2—C1—C6	118.51 (11)	C8—C9—H9	119.5
C2—C1—C7	122.17 (10)	C11—C10—C9	119.94 (12)
C6—C1—C7	119.32 (10)	C11—C10—H10	120.0
C3—C2—C1	120.61 (12)	C9—C10—H10	120.0
C3—C2—H2	119.7	C12—C11—C10	119.77 (11)
C1—C2—H2	119.7	C12—C11—H11	120.1
C4—C3—C2	120.34 (12)	C10—C11—H11	120.1
C4—C3—H3	119.8	C11—C12—C13	120.25 (11)
C2—C3—H3	119.8	C11—C12—H12	119.9
C3—C4—C5	119.69 (11)	C13—C12—H12	119.9
C3—C4—H4	120.2	C8—C13—C12	120.59 (11)
C5—C4—H4	120.2	C8—C13—H13	119.7
C4—C5—C6	120.15 (12)	C12—C13—H13	119.7
C4—C5—H5	119.9	C15—C14—C7	111.41 (9)
C6—C5—H5	119.9	C15—C14—H14A	109.3
C5—C6—C1	120.69 (11)	C7—C14—H14A	109.3
C5—C6—H6	119.7	C15—C14—H14B	109.3
C1—C6—H6	119.7	C7—C14—H14B	109.3
O1—C7—C1	109.72 (9)	H14A—C14—H14B	108.0
O1—C7—C8	105.71 (8)	C16—C15—C14	174.11 (12)
C1—C7—C8	112.75 (9)	C15—C16—C17	178.17 (13)
O1—C7—C14	107.11 (9)	O2—C17—C16	112.13 (10)
C1—C7—C14	112.10 (9)	O2—C17—H17A	109.2
C8—C7—C14	109.10 (9)	C16—C17—H17A	109.2
C13—C8—C9	118.48 (11)	O2—C17—H17B	109.2
C13—C8—C7	122.46 (10)	C16—C17—H17B	109.2
C9—C8—C7	119.06 (10)	H17A—C17—H17B	107.9
C6—C1—C2—C3	0.37 (17)	C14—C7—C8—C13	−115.62 (12)
C7—C1—C2—C3	−178.85 (11)	O1—C7—C8—C9	−50.95 (13)
C1—C2—C3—C4	0.18 (19)	C1—C7—C8—C9	−170.83 (10)
C2—C3—C4—C5	−0.24 (19)	C14—C7—C8—C9	63.93 (13)
C3—C4—C5—C6	−0.26 (18)	C13—C8—C9—C10	−0.35 (18)
C4—C5—C6—C1	0.83 (18)	C7—C8—C9—C10	−179.92 (11)
C2—C1—C6—C5	−0.88 (17)	C8—C9—C10—C11	0.34 (19)
C7—C1—C6—C5	178.37 (10)	C9—C10—C11—C12	−0.10 (19)
C2—C1—C7—O1	138.56 (11)	C10—C11—C12—C13	−0.11 (19)
C6—C1—C7—O1	−40.66 (13)	C9—C8—C13—C12	0.13 (17)
C2—C1—C7—C8	−103.91 (12)	C7—C8—C13—C12	179.69 (10)
C6—C1—C7—C8	76.87 (13)	C11—C12—C13—C8	0.09 (18)
C2—C1—C7—C14	19.69 (14)	O1—C7—C14—C15	−60.24 (11)
C6—C1—C7—C14	−159.53 (10)	C1—C7—C14—C15	60.16 (12)
O1—C7—C8—C13	129.49 (11)	C8—C7—C14—C15	−174.22 (9)
C1—C7—C8—C13	9.62 (15)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.86	1.91	2.7493 (12)	164
O2—H2′···O1^ii	0.86	1.87	2.7056 (12)	164
C5—H5···Cg2^iii	0.95	2.80	3.7122 (13)	160
C17—H17A···Cg1^i	0.99	3.00	3.6172 (13)	122

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z−1; (iii) x+1, y, z.