Crystal structure of (Z)-1-phenyl-3-styryl­undeca-2-en-4,10-diyn-1-ol

Ganguly, R.; Sally; Chan, P.W.H.

doi:10.1107/S205698901402742X

organic compounds

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ISSN: 2056-9890

Volume 71| Part 1| January 2015| Page o64

https://doi.org/10.1107/S205698901402742X

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Crystal structure of (Z)-1-phenyl-3-styrylundeca-2-en-4,10-diyn-1-ol

Rakesh Ganguly,^a ^* Sally ^b and Philip Wai Hong Chan ^b

^aDivision of Chemistry & Biological Chemistry, SPMS-CBC-01-18D, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore, and ^bDivision of Chemistry & Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore
^*Correspondence e-mail: rganguly@ntu.edu.sg

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 December 2014; accepted 16 December 2014; online 1 January 2015)

The molecule of the title compound, C₂₅H₂₄O, obtained by acid-catalysed 1,3-migration of an alcohol group, is T-shaped. The planes of the two phenyl rings are inclined to one another by 81.9 (2)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming chains along [001].

Keywords: crystal structure; 1,3-migration; alcohol group; catalytic cyclization; styrylundecanene..

CCDC reference: 1009363

1. Related literature

For the 1,3-migration of an alcoholic group adjacent to a vinyl group in the presence of a Lewis acid, see: Piotti & Alper (1997 ); Poloukhtine & Popik (2005 ). For catalytic cyclization of alcohols containing a number of unsaturated groups, see: Teo et al. (2014 ).

2. Experimental

2.1. Crystal data

C₂₅H₂₄O
M_r = 340.44
Trigonal, P 3₂
a = 17.867 (2) Å
c = 5.3290 (6) Å
V = 1473.3 (4) Å³
Z = 3
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 103 K
0.34 × 0.04 × 0.04 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.74, T_max = 1.00
14182 measured reflections
4846 independent reflections
2945 reflections with I > 2σ(I)
R_int = 0.078

2.3. Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.129
S = 0.98
4846 reflections
235 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O1ⁱ	0.84	1.83	2.652 (3)	166
Symmetry code: (i) $[-y+1, x-y+1, z-{\script{1\over 3}}]$ .

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL2014, PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1009363

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S205698901402742X/su5038sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901402742X/su5038Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901402742X/su5038Isup3.cml

checkCIF report

Comment top

1,3-migration of an alcoholic group adjacent to a vinyl group in the presence of a Lewis-acid is widely known (Piotti & Alper, 1997). One such example was demonstrated recently in the preparation of 4-(α-hydroxybenzyl)-1-tert-butyldimethylsilyloxy-4-cyclodecene-2,6-diyne (Poloukhtine & Popik, 2005). In addition, alcohols containing many unsaturated groups provide an access to a myriad of types of functionalization such as catalytic cyclization (Teo et al., 2014). Herein, we report on the synthesis and crystal structure of the title compound, obtained by the acid-catalyzed 1,3-migration of an alcoholic group.

The molecular structure of the title compound is illustrated in Fig. 1. The molecule is T-shaped with the two phenyl ring inclined to one another by 81.9 (2) °.

In the crystal, molecules are linked by O—H···O hydrogen bonds forming chains along the c axis direction (Table 1 and Fig. 2).

Synthesis and crystallization top

The synthesis of the title compound is illustrated in Fig. 3. (Z)-1-phenyl-3-styrylundeca-1-en-4,10-diyn-3-ol (1mmol, 340.5 mg) was dissolved in 10 ml of CH₂Cl₂. DMAP [4-(dimethylamino)pyridine; 0.1 mmol, 12 mg], triethylamine (5 mmol, 0.70 ml) and acetic anhydride (5 mmol, 0.47 ml) were added sequentially and the reaction mixture was stirred overnight. It was then washed with saturated sodium bicarbonate and extracted twice with CH₂Cl₂. The organic layers were combined, dried with MgSO₄ and the solvent was removed under reduced pressure. The resulting oil was purified by column chromatography with hexane/ethylacetate as eluent. The product was recrystallized with ethylacetate to give a colourless compound in 80% yield. Slow evaporation of a solution in ethylacetate gave needle-like crystals. ¹H NMR (400 MHz, CDCl₃) 1.71–1.83 (m, 4H), 1.97 (t, 1H), 2.20 (s, 1H), 2.26–2.30 (m, 2H), 2.55 (t, 2), 5.90 (d, 1H), 6.09 (d, 1H), 6.68 (d, 1H), 6.99 (d, 1H), 7.21–7.47 (m, 10H) 13 C NMR (100 MHz, CDCl3) 18.0, 19.2, 27.7, 27.7, 68.8, 72.5, 75.3, 84.0, 97.9, 124.1, 125.9, 126.8, 127.7, 127.9, 128.6, 128.6, 132.4, 136.8, 140.4, 142.7

Refinement top

The OH and C-bound H atoms were included in calculated positions and treated as riding atoms: O—H = 0.84 Å, C—H = 0.95 - 1.00 Å with U_iso(H) = 1.5U_eq(O) for the OH H atom and = 1.2U_eq(C) for other H atoms.

Related literature top

For the 1,3-migration of an alcoholic group adjacent to a vinyl group in the presence of a Lewis acid, see: Piotti & Alper (1997); Poloukhtine & Popik (2005). For catalytic cyclization of alcohols containing a number of unsaturated groups, see: Teo et al. (2014).

Structure description top

The molecular structure of the title compound is illustrated in Fig. 1. The molecule is T-shaped with the two phenyl ring inclined to one another by 81.9 (2) °.

In the crystal, molecules are linked by O—H···O hydrogen bonds forming chains along the c axis direction (Table 1 and Fig. 2).

For the 1,3-migration of an alcoholic group adjacent to a vinyl group in the presence of a Lewis acid, see: Piotti & Alper (1997); Poloukhtine & Popik (2005). For catalytic cyclization of alcohols containing a number of unsaturated groups, see: Teo et al. (2014).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial view along the c axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).
	Fig. 3. Reaction scheme.

(Z)-1-Phenyl-3-styrylundeca-2-en-4,10-diyn-1-ol top

Crystal data top

C₂₅H₂₄O	D_x = 1.151 Mg m⁻³
M_r = 340.44	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3₂	Cell parameters from 1285 reflections
a = 17.867 (2) Å	θ = 2.3–20.5°
c = 5.3290 (6) Å	µ = 0.07 mm⁻¹
V = 1473.3 (4) Å³	T = 103 K
Z = 3	Needle, colourless
F(000) = 546	0.34 × 0.04 × 0.04 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4846 independent reflections
Radiation source: fine-focus sealed tube	2945 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ω and φ scan	θ_max = 28.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −23→14
T_min = 0.74, T_max = 1.00	k = −22→23
14182 measured reflections	l = −7→7

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0486P)²] where P = (F_o² + 2F_c²)/3
4846 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₅H₂₄O	Z = 3
M_r = 340.44	Mo Kα radiation
Trigonal, P3₂	µ = 0.07 mm⁻¹
a = 17.867 (2) Å	T = 103 K
c = 5.3290 (6) Å	0.34 × 0.04 × 0.04 mm
V = 1473.3 (4) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	4846 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2945 reflections with I > 2σ(I)
T_min = 0.74, T_max = 1.00	R_int = 0.078
14182 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.129	H-atom parameters constrained
S = 0.98	Δρ_max = 0.39 e Å⁻³
4846 reflections	Δρ_min = −0.24 e Å⁻³
235 parameters

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	U_iso*/U_eq
O1	0.30859 (17)	0.59437 (17)	0.3483 (5)	0.0251 (7)
H1A	0.3463	0.6311	0.2521	0.038*
C1	0.3069 (3)	0.5136 (2)	0.3226 (7)	0.0199 (9)
H1	0.3048	0.4898	0.4940	0.024*
C2	0.2281 (2)	0.4484 (3)	0.1774 (7)	0.0197 (9)
C3	0.1897 (3)	0.3614 (3)	0.2407 (8)	0.0281 (10)
H3	0.2105	0.3441	0.3801	0.034*
C4	0.1209 (3)	0.2999 (3)	0.1007 (9)	0.0341 (12)
H4	0.0948	0.2407	0.1461	0.041*
C5	0.0899 (3)	0.3235 (3)	−0.1032 (9)	0.0333 (11)
H5	0.0434	0.2809	−0.1998	0.040*
C6	0.1275 (3)	0.4099 (3)	−0.1651 (8)	0.0305 (11)
H6	0.1060	0.4269	−0.3038	0.037*
C7	0.1962 (3)	0.4721 (3)	−0.0270 (8)	0.0272 (10)
H7	0.2216	0.5313	−0.0722	0.033*
C8	0.3878 (2)	0.5282 (2)	0.1948 (7)	0.0196 (9)
H8	0.4050	0.5639	0.0497	0.024*
C9	0.4386 (2)	0.4964 (2)	0.2634 (7)	0.0160 (8)
C10	0.5143 (2)	0.5153 (2)	0.1121 (7)	0.0171 (8)
H10	0.5253	0.5510	−0.0311	0.021*
C11	0.5691 (2)	0.4869 (2)	0.1575 (7)	0.0171 (8)
H11	0.5608	0.4552	0.3082	0.021*
C12	0.6413 (2)	0.5000 (2)	−0.0039 (7)	0.0173 (9)
C13	0.6850 (2)	0.4550 (2)	0.0458 (7)	0.0184 (9)
H13	0.6692	0.4182	0.1882	0.022*
C14	0.7511 (3)	0.4630 (3)	−0.1091 (8)	0.0220 (9)
H14	0.7805	0.4324	−0.0718	0.026*
C15	0.7739 (3)	0.5160 (3)	−0.3182 (7)	0.0245 (10)
H15	0.8184	0.5209	−0.4264	0.029*
C16	0.7321 (2)	0.5620 (3)	−0.3704 (7)	0.0231 (9)
H16	0.7482	0.5985	−0.5134	0.028*
C17	0.6665 (3)	0.5545 (3)	−0.2137 (7)	0.0204 (9)
H17	0.6385	0.5867	−0.2492	0.024*
C18	0.4152 (2)	0.4385 (3)	0.4758 (8)	0.0184 (8)
C19	0.3892 (2)	0.3880 (2)	0.6457 (7)	0.0201 (9)
C20	0.3519 (3)	0.3267 (3)	0.8553 (8)	0.0275 (10)
H20A	0.3052	0.3336	0.9313	0.033*
H20B	0.3973	0.3426	0.9844	0.033*
C21	0.3157 (3)	0.2328 (3)	0.7913 (8)	0.0310 (11)
H21A	0.2888	0.1977	0.9434	0.037*
H21B	0.3637	0.2235	0.7405	0.037*
C22	0.2484 (3)	0.2009 (3)	0.5807 (8)	0.0317 (11)
H22A	0.2021	0.2137	0.6248	0.038*
H22B	0.2760	0.2322	0.4237	0.038*
C23	0.2091 (3)	0.1044 (3)	0.5383 (9)	0.0467 (14)
H23A	0.1740	0.0881	0.3830	0.056*
H23B	0.2562	0.0913	0.5127	0.056*
C24	0.1549 (3)	0.0521 (3)	0.7450 (9)	0.0326 (11)
C25	0.1097 (3)	0.0105 (3)	0.9069 (10)	0.0431 (13)
H25	0.0727	−0.0235	1.0394	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0252 (16)	0.0188 (15)	0.0341 (17)	0.0130 (13)	0.0087 (14)	0.0019 (13)
C1	0.024 (2)	0.021 (2)	0.021 (2)	0.0159 (19)	0.0076 (18)	0.0067 (18)
C2	0.019 (2)	0.021 (2)	0.024 (2)	0.0129 (18)	0.0084 (18)	0.0036 (18)
C3	0.022 (2)	0.025 (2)	0.036 (3)	0.010 (2)	0.002 (2)	0.008 (2)
C4	0.026 (2)	0.026 (3)	0.047 (3)	0.010 (2)	0.003 (2)	0.005 (2)
C5	0.024 (2)	0.034 (3)	0.038 (3)	0.011 (2)	−0.001 (2)	−0.006 (2)
C6	0.031 (3)	0.035 (3)	0.030 (3)	0.020 (2)	−0.005 (2)	−0.002 (2)
C7	0.028 (2)	0.027 (2)	0.029 (2)	0.016 (2)	0.003 (2)	0.005 (2)
C8	0.020 (2)	0.018 (2)	0.021 (2)	0.0093 (18)	0.0026 (17)	0.0022 (17)
C9	0.016 (2)	0.0124 (19)	0.019 (2)	0.0071 (17)	−0.0012 (17)	−0.0009 (16)
C10	0.018 (2)	0.0110 (19)	0.019 (2)	0.0051 (17)	0.0007 (17)	0.0011 (16)
C11	0.019 (2)	0.015 (2)	0.017 (2)	0.0078 (18)	0.0010 (17)	0.0004 (16)
C12	0.014 (2)	0.017 (2)	0.020 (2)	0.0066 (17)	−0.0008 (17)	−0.0034 (17)
C13	0.018 (2)	0.019 (2)	0.018 (2)	0.0087 (18)	0.0014 (17)	0.0001 (17)
C14	0.021 (2)	0.025 (2)	0.024 (2)	0.0145 (19)	−0.0020 (18)	−0.0037 (19)
C15	0.019 (2)	0.031 (2)	0.023 (2)	0.012 (2)	0.0035 (18)	−0.0035 (19)
C16	0.021 (2)	0.025 (2)	0.022 (2)	0.0096 (19)	0.0035 (18)	0.0020 (19)
C17	0.017 (2)	0.021 (2)	0.025 (2)	0.0119 (18)	−0.0006 (18)	0.0014 (18)
C18	0.015 (2)	0.020 (2)	0.021 (2)	0.0094 (17)	−0.0002 (17)	−0.0042 (18)
C19	0.017 (2)	0.020 (2)	0.021 (2)	0.0073 (18)	0.0002 (18)	0.0011 (18)
C20	0.031 (3)	0.024 (2)	0.020 (2)	0.008 (2)	−0.001 (2)	0.0045 (19)
C21	0.033 (3)	0.026 (2)	0.027 (2)	0.010 (2)	0.002 (2)	0.002 (2)
C22	0.032 (3)	0.024 (2)	0.029 (3)	0.006 (2)	0.003 (2)	0.003 (2)
C23	0.055 (3)	0.028 (3)	0.039 (3)	0.007 (2)	0.006 (3)	−0.002 (2)
C24	0.033 (3)	0.019 (2)	0.043 (3)	0.010 (2)	−0.004 (2)	−0.003 (2)
C25	0.037 (3)	0.029 (3)	0.054 (4)	0.009 (2)	0.001 (3)	0.006 (3)

Geometric parameters (Å, º) top

O1—C1	1.435 (4)	C13—C14	1.388 (5)
O1—H1A	0.8400	C13—H13	0.9500
C1—C8	1.498 (5)	C14—C15	1.385 (6)
C1—C2	1.516 (6)	C14—H14	0.9500
C1—H1	1.0000	C15—C16	1.388 (6)
C2—C3	1.390 (5)	C15—H15	0.9500
C2—C7	1.390 (5)	C16—C17	1.390 (5)
C3—C4	1.387 (6)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.378 (6)	C18—C19	1.197 (5)
C4—H4	0.9500	C19—C20	1.470 (5)
C5—C6	1.381 (6)	C20—C21	1.504 (6)
C5—H5	0.9500	C20—H20A	0.9900
C6—C7	1.385 (6)	C20—H20B	0.9900
C6—H6	0.9500	C21—C22	1.531 (6)
C7—H7	0.9500	C21—H21A	0.9900
C8—C9	1.341 (5)	C21—H21B	0.9900
C8—H8	0.9500	C22—C23	1.519 (6)
C9—C18	1.446 (5)	C22—H22A	0.9900
C9—C10	1.461 (5)	C22—H22B	0.9900
C10—C11	1.332 (5)	C23—C24	1.456 (7)
C10—H10	0.9500	C23—H23A	0.9900
C11—C12	1.467 (5)	C23—H23B	0.9900
C11—H11	0.9500	C24—C25	1.161 (6)
C12—C13	1.399 (5)	C25—H25	0.9500
C12—C17	1.401 (5)

C1—O1—H1A	109.5	C12—C13—H13	119.4
O1—C1—C8	109.5 (3)	C15—C14—C13	119.5 (4)
O1—C1—C2	111.5 (3)	C15—C14—H14	120.2
C8—C1—C2	110.3 (3)	C13—C14—H14	120.2
O1—C1—H1	108.5	C14—C15—C16	120.3 (4)
C8—C1—H1	108.5	C14—C15—H15	119.9
C2—C1—H1	108.5	C16—C15—H15	119.9
C3—C2—C7	118.8 (4)	C15—C16—C17	120.1 (4)
C3—C2—C1	119.0 (4)	C15—C16—H16	120.0
C7—C2—C1	122.0 (4)	C17—C16—H16	120.0
C2—C3—C4	120.2 (4)	C16—C17—C12	120.6 (4)
C2—C3—H3	119.9	C16—C17—H17	119.7
C4—C3—H3	119.9	C12—C17—H17	119.7
C5—C4—C3	120.9 (4)	C19—C18—C9	174.8 (4)
C5—C4—H4	119.5	C18—C19—C20	176.0 (4)
C3—C4—H4	119.5	C19—C20—C21	116.2 (4)
C4—C5—C6	119.0 (4)	C19—C20—H20A	108.2
C4—C5—H5	120.5	C21—C20—H20A	108.2
C6—C5—H5	120.5	C19—C20—H20B	108.2
C5—C6—C7	120.7 (4)	C21—C20—H20B	108.2
C5—C6—H6	119.6	H20A—C20—H20B	107.4
C7—C6—H6	119.6	C20—C21—C22	113.6 (4)
C6—C7—C2	120.4 (4)	C20—C21—H21A	108.8
C6—C7—H7	119.8	C22—C21—H21A	108.8
C2—C7—H7	119.8	C20—C21—H21B	108.8
C9—C8—C1	126.9 (3)	C22—C21—H21B	108.8
C9—C8—H8	116.5	H21A—C21—H21B	107.7
C1—C8—H8	116.5	C23—C22—C21	111.3 (4)
C8—C9—C18	120.1 (3)	C23—C22—H22A	109.4
C8—C9—C10	119.7 (3)	C21—C22—H22A	109.4
C18—C9—C10	120.0 (3)	C23—C22—H22B	109.4
C11—C10—C9	125.7 (4)	C21—C22—H22B	109.4
C11—C10—H10	117.1	H22A—C22—H22B	108.0
C9—C10—H10	117.1	C24—C23—C22	113.4 (4)
C10—C11—C12	125.9 (4)	C24—C23—H23A	108.9
C10—C11—H11	117.0	C22—C23—H23A	108.9
C12—C11—H11	117.0	C24—C23—H23B	108.9
C13—C12—C17	118.2 (3)	C22—C23—H23B	108.9
C13—C12—C11	119.7 (4)	H23A—C23—H23B	107.7
C17—C12—C11	122.1 (3)	C25—C24—C23	178.0 (5)
C14—C13—C12	121.3 (4)	C24—C25—H25	180.0
C14—C13—H13	119.4

O1—C1—C2—C3	−145.9 (3)	C8—C9—C10—C11	−179.1 (4)
C8—C1—C2—C3	92.2 (4)	C18—C9—C10—C11	−3.5 (6)
O1—C1—C2—C7	38.1 (5)	C9—C10—C11—C12	175.0 (3)
C8—C1—C2—C7	−83.8 (4)	C10—C11—C12—C13	−169.7 (4)
C7—C2—C3—C4	0.2 (6)	C10—C11—C12—C17	8.1 (6)
C1—C2—C3—C4	−175.9 (4)	C17—C12—C13—C14	−0.6 (5)
C2—C3—C4—C5	0.4 (6)	C11—C12—C13—C14	177.2 (3)
C3—C4—C5—C6	−1.0 (7)	C12—C13—C14—C15	−0.6 (6)
C4—C5—C6—C7	1.0 (7)	C13—C14—C15—C16	1.1 (6)
C5—C6—C7—C2	−0.3 (7)	C14—C15—C16—C17	−0.5 (6)
C3—C2—C7—C6	−0.2 (6)	C15—C16—C17—C12	−0.8 (6)
C1—C2—C7—C6	175.8 (4)	C13—C12—C17—C16	1.3 (5)
O1—C1—C8—C9	133.8 (4)	C11—C12—C17—C16	−176.5 (4)
C2—C1—C8—C9	−103.1 (4)	C19—C20—C21—C22	−54.5 (5)
C1—C8—C9—C18	2.6 (6)	C20—C21—C22—C23	−175.6 (4)
C1—C8—C9—C10	178.2 (3)	C21—C22—C23—C24	68.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1ⁱ	0.84	1.83	2.652 (3)	166

Symmetry code: (i) −y+1, x−y+1, z−1/3.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1ⁱ	0.84	1.83	2.652 (3)	166

Symmetry code: (i) −y+1, x−y+1, z−1/3.

References

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