(Z)-3-(4-Methyl­benzyl­idene)-4-oxo­penta­noic acid

Boukharsa, Y.; Abba Touré, H.; Taoufik, J.; Benzeid, H.; Ansar, M.

doi:10.1107/S2414314616020034

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 12| December 2016| x162003

https://doi.org/10.1107/S2414314616020034

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(Z)-3-(4-Methylbenzylidene)-4-oxopentanoic acid

Youness Boukharsa,^a Hamadoun Abba Touré,^b Jamal Taoufik,^a Hanane Benzeid ^b ^* and M'hammed Ansar ^a

^aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, BP 6203, Rabat Institute, University Mohammed V, Rabat, Morocco, and ^bLaboratory of Analytical Chemistry, Faculty of Medicine and Pharmacy, BP 6203, Rabat Institute, University Mohammed V, Rabat, Morocco
^*Correspondence e-mail: benzeid_hanane@yahoo.fr

Edited by J. Simpson, University of Otago, New Zealand (Received 8 December 2016; accepted 16 December 2016; online 20 December 2016)

The title compound, C₁₃H₁₄O₃, a levulinic acid derivative, crystallizes with two independent molecules (A and B) in the asymmetric unit. The compound adopts a Z configuration about the C=C bonds in both molecules. The dihedral angle between the toluene ring and the carboxylic acid group is 72.83 (7)° in molecule A and 83.64 (8)° in molecule B. The toluene rings are inclined to the ketone substituents by 27.03 (9)° for A and 30.84 (6)° for B. In the crystal, like molecules are linked by pairs of O—H⋯O hydrogen bonds, forming A–A and B-B inversion dimers.

Keywords: crystal structure; levulinic acid derivative; hydrogen bonding.

CCDC reference: 1523139

Structure description

Levulinic acid derivatives are known to possess a wide spectrum of pharmacological activities and are used in photodynamic therapy in gastroenterology (Mordon et al. 2005 ) and as drugs for prostate cancer (Colin et al. 2011 ). They are also reactants for the synthesis of other heterocyclic compounds such as pyridazinone derivatives (Boukharsa et al. 2015 , 2016 ).

In this paper we report the crystal structure determination of the title compound, Fig. 1, which crystallizes with two independent molecules (A and B) in the asymmetric unit. The dihedral angles between the toluene ring planes and the carboxylic acid groups O4/C14/O5/C15 and O1/O2/C1/C2/C3 are 72.83 (7)° in molecule A and 83.64 (8)° in molecule B. The toluene rings are inclined to the C16/C24/O6/C25 and C3/C11/O3/C12 ketone substituents by 27.03 (9)° for A and 30.84 (6)° for B.

Figure 1
The asymmetric unit of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are shown at the 50% probability level.

In the title compound, the C—O [1.3056 (15) and 1.2981 (13) Å] and C=O [1.2132 (16) and 1.2201 (14) Å] bond distances agree well with the values given by Allen et al. (1987 ) for a variety of carboxylic acid groups (C—O 1.308 Å and C=O 1.214 Å). The bond angles at the central C atoms in the carboxylic acid groups [O1—C1—C2 123.22 (12), O2—C1—C2 113.64 (12)° and O4–C14–C15 122.88 (10) and O5–C14–C15 123.19 (10)°] are also similar to the mean values specified by Borthwick (1980 ) for a typical carboxylic acids [O2—C1—C2 123 (2)°, O1—C1—C2 112 (2)°].

In the crystal, molecules are linked by pairs of O2—H2⋯O1 and O5—H5⋯O4 hydrogen bonds (Table 1, Figs. 2 and 3), forming classical A–A and B–B carboxylic acid inversion dimers.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O4ⁱ	0.82	1.82	2.6310 (12)	171
O2—H2⋯O1ⁱⁱ	0.82	1.85	2.6714 (15)	177
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y+2, -z+1.

Figure 2
A view of the pairs of A–A and B–B inversion dimers formed by O—H⋯O hydrogen bonds.

Figure 3
The three-dimensional structure in the unit cell, viewed along the b axis. Hydrogen-bonding interactions are shown as dashed lines.

Synthesis and crystallization

An ice-cooled mixture of o-methylbenzaldehyde (0.02 mol) and levulinic acid (0.03 mol) was saturated with dry hydrogen chloride (HCl). Then, the mixture was stirred for 24 h at room temperature. The resulting precipitate was filtered off and washed with ethyl acetate. The crude product was crystallized from ethanol to afford colourless crystals (yield = 87%; m.p. = 144°C) (Boukharsa et al. 2016, El Marrakchi et al. 2014 )].

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₄O₃
M_r	218.25
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	296
a, b, c (Å)	9.2491 (5), 18.1423 (10), 14.3719 (7)
β (°)	96.610 (3)
V (Å³)	2395.6 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.3 × 0.2 × 0.15

Data collection
Diffractometer	Bruker X8 APEX
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.91, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	129996, 7673, 5039
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.726

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.174, 1.05
No. of reflections	7673
No. of parameters	295
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.16
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1523139

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314616020034/sj4079sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616020034/sj4079Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616020034/sj4079Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

(Z)-3-(4-Methylbenzylidene)-4-oxopentanoic acid top

Crystal data top

C₁₃H₁₄O₃	F(000) = 928
M_r = 218.25	D_x = 1.210 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
a = 9.2491 (5) Å	Cell parameters from 7673 reflections
b = 18.1423 (10) Å	θ = 2.3–31.1°
c = 14.3719 (7) Å	µ = 0.09 mm⁻¹
β = 96.610 (3)°	T = 296 K
V = 2395.6 (2) Å³	Block, colourless
Z = 8	0.3 × 0.2 × 0.15 mm

Data collection top

Bruker X8 APEX diffractometer	7673 independent reflections
Radiation source: fine-focus sealed tube	5039 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
Detector resolution: 7.9 pixels mm^-1	θ_max = 31.1°, θ_min = 2.3°
ω and φ scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −26→26
T_min = 0.91, T_max = 0.98	l = −18→20
129996 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.174	w = 1/[σ²(F_o²) + (0.0946P)² + 0.1975P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
7673 reflections	Δρ_max = 0.31 e Å⁻³
295 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C16	0.13525 (12)	0.70579 (6)	0.12254 (8)	0.0392 (2)
C14	0.09904 (12)	0.57199 (6)	0.08109 (8)	0.0387 (2)
O4	−0.00001 (11)	0.58848 (5)	0.02117 (7)	0.0599 (3)
C17	0.04540 (12)	0.74580 (6)	0.16941 (8)	0.0416 (2)
H17	0.0348	0.7949	0.1511	0.050*
O5	0.14539 (12)	0.50486 (5)	0.09445 (7)	0.0624 (3)
H5	0.0926	0.4767	0.0613	0.094*
O6	0.28038 (12)	0.69915 (6)	0.00008 (8)	0.0663 (3)
C15	0.17930 (13)	0.62729 (6)	0.14503 (8)	0.0430 (2)
H15A	0.2828	0.6221	0.1412	0.052*
H15B	0.1622	0.6166	0.2090	0.052*
C18	−0.03845 (13)	0.72349 (6)	0.24511 (8)	0.0433 (3)
C24	0.20185 (13)	0.73769 (7)	0.04260 (8)	0.0453 (3)
C19	−0.09393 (16)	0.65281 (7)	0.25495 (11)	0.0574 (3)
H19	−0.0774	0.6166	0.2116	0.069*
C23	−0.07381 (15)	0.77700 (7)	0.30853 (9)	0.0518 (3)
H23	−0.0441	0.8255	0.3017	0.062*
C25	0.17203 (18)	0.81607 (8)	0.01331 (11)	0.0616 (4)
H25A	0.0695	0.8225	−0.0044	0.092*
H25B	0.2239	0.8276	−0.0390	0.092*
H25C	0.2036	0.8484	0.0646	0.092*
C22	−0.15266 (16)	0.75873 (9)	0.38157 (10)	0.0613 (4)
H22	−0.1735	0.7951	0.4236	0.074*
C21	−0.20095 (16)	0.68771 (9)	0.39341 (10)	0.0608 (3)
C20	−0.17302 (18)	0.63566 (9)	0.32788 (12)	0.0658 (4)
H20	−0.2082	0.5880	0.3329	0.079*
C26	−0.2846 (2)	0.66728 (13)	0.47373 (13)	0.0872 (6)
H26A	−0.2198	0.6452	0.5229	0.131*
H26B	−0.3600	0.6328	0.4524	0.131*
H26C	−0.3273	0.7108	0.4971	0.131*
C3	0.01570 (14)	1.08093 (7)	0.21990 (8)	0.0465 (3)
O1	0.06317 (11)	1.04595 (6)	0.41565 (7)	0.0700 (3)
O2	−0.15248 (12)	0.99179 (7)	0.40738 (8)	0.0734 (3)
H2	−0.1222	0.9794	0.4609	0.110*
C4	0.07038 (15)	1.14814 (7)	0.20654 (8)	0.0488 (3)
H4	0.1413	1.1498	0.1657	0.059*
C5	0.03529 (15)	1.21933 (7)	0.24653 (9)	0.0486 (3)
O3	0.02795 (14)	0.95429 (6)	0.19154 (10)	0.0786 (3)
C2	−0.10518 (14)	1.06384 (8)	0.27826 (9)	0.0521 (3)
H2A	−0.1592	1.1088	0.2865	0.063*
H2B	−0.1714	1.0291	0.2444	0.063*
C1	−0.05470 (14)	1.03229 (7)	0.37301 (9)	0.0498 (3)
C11	0.06928 (16)	1.01546 (7)	0.17210 (10)	0.0557 (3)
C10	0.04781 (18)	1.28227 (8)	0.19252 (11)	0.0628 (4)
H10	0.0781	1.2780	0.1333	0.075*
C9	0.0157 (2)	1.35095 (8)	0.22602 (13)	0.0708 (4)
H9	0.0228	1.3920	0.1880	0.085*
C6	−0.0045 (2)	1.22914 (8)	0.33599 (10)	0.0686 (4)
H6	−0.0104	1.1885	0.3748	0.082*
C8	−0.02629 (17)	1.36043 (8)	0.31340 (13)	0.0656 (4)
C7	−0.0355 (2)	1.29855 (9)	0.36803 (13)	0.0755 (5)
H7	−0.0632	1.3036	0.4279	0.091*
C12	0.1763 (2)	1.02402 (9)	0.10182 (14)	0.0850 (6)
H12A	0.2635	1.0468	0.1313	0.128*
H12B	0.1345	1.0543	0.0509	0.128*
H12C	0.1992	0.9764	0.0783	0.128*
C13	−0.0593 (3)	1.43579 (10)	0.35049 (19)	0.0979 (7)
H13A	−0.1600	1.4474	0.3327	0.147*
H13B	0.0007	1.4719	0.3248	0.147*
H13C	−0.0396	1.4359	0.4175	0.147*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C16	0.0393 (5)	0.0342 (5)	0.0431 (5)	−0.0027 (4)	0.0007 (4)	−0.0051 (4)
C14	0.0429 (5)	0.0330 (5)	0.0408 (5)	0.0002 (4)	0.0072 (4)	−0.0007 (4)
O4	0.0634 (6)	0.0388 (4)	0.0713 (6)	0.0057 (4)	−0.0183 (5)	−0.0112 (4)
C17	0.0439 (6)	0.0341 (5)	0.0462 (6)	−0.0009 (4)	0.0019 (4)	−0.0032 (4)
O5	0.0852 (7)	0.0319 (4)	0.0637 (6)	0.0025 (4)	−0.0193 (5)	−0.0019 (4)
O6	0.0717 (7)	0.0660 (6)	0.0657 (6)	0.0078 (5)	0.0266 (5)	−0.0053 (5)
C15	0.0436 (6)	0.0361 (5)	0.0482 (6)	0.0011 (4)	0.0008 (5)	−0.0045 (4)
C18	0.0423 (6)	0.0419 (6)	0.0455 (6)	0.0032 (4)	0.0044 (5)	−0.0032 (4)
C24	0.0433 (6)	0.0447 (6)	0.0480 (6)	−0.0051 (5)	0.0054 (5)	−0.0051 (5)
C19	0.0628 (8)	0.0451 (7)	0.0677 (8)	−0.0040 (6)	0.0215 (7)	−0.0079 (6)
C23	0.0554 (7)	0.0469 (6)	0.0534 (7)	0.0041 (5)	0.0078 (6)	−0.0071 (5)
C25	0.0718 (9)	0.0494 (7)	0.0654 (8)	−0.0062 (6)	0.0157 (7)	0.0081 (6)
C22	0.0626 (8)	0.0692 (9)	0.0538 (7)	0.0071 (7)	0.0138 (6)	−0.0123 (6)
C21	0.0527 (7)	0.0751 (9)	0.0561 (8)	0.0068 (7)	0.0134 (6)	0.0073 (7)
C20	0.0665 (9)	0.0574 (8)	0.0772 (10)	−0.0043 (7)	0.0237 (8)	0.0057 (7)
C26	0.0783 (11)	0.1172 (16)	0.0709 (11)	0.0043 (11)	0.0297 (9)	0.0171 (10)
C3	0.0565 (7)	0.0444 (6)	0.0386 (5)	0.0011 (5)	0.0052 (5)	0.0067 (4)
O1	0.0603 (6)	0.0935 (8)	0.0553 (5)	−0.0173 (5)	0.0034 (5)	0.0272 (5)
O2	0.0680 (7)	0.0907 (8)	0.0612 (6)	−0.0252 (6)	0.0072 (5)	0.0242 (6)
C4	0.0609 (7)	0.0447 (6)	0.0422 (6)	0.0004 (5)	0.0117 (5)	0.0032 (5)
C5	0.0566 (7)	0.0441 (6)	0.0461 (6)	−0.0024 (5)	0.0096 (5)	0.0031 (5)
O3	0.0910 (8)	0.0423 (5)	0.1056 (9)	−0.0033 (5)	0.0243 (7)	0.0054 (5)
C2	0.0519 (7)	0.0565 (7)	0.0480 (6)	−0.0022 (6)	0.0054 (5)	0.0083 (5)
C1	0.0531 (7)	0.0497 (6)	0.0478 (6)	−0.0048 (5)	0.0116 (5)	0.0078 (5)
C11	0.0659 (8)	0.0439 (6)	0.0575 (7)	0.0017 (6)	0.0082 (6)	0.0034 (5)
C10	0.0833 (10)	0.0482 (7)	0.0602 (8)	−0.0094 (7)	0.0223 (7)	0.0059 (6)
C9	0.0897 (11)	0.0441 (7)	0.0804 (10)	−0.0052 (7)	0.0169 (9)	0.0099 (7)
C6	0.1076 (13)	0.0497 (7)	0.0519 (8)	0.0014 (7)	0.0235 (8)	0.0034 (6)
C8	0.0626 (9)	0.0484 (7)	0.0857 (10)	0.0020 (6)	0.0081 (8)	−0.0074 (7)
C7	0.1064 (14)	0.0575 (9)	0.0670 (9)	0.0010 (8)	0.0295 (9)	−0.0100 (7)
C12	0.1175 (15)	0.0563 (9)	0.0903 (12)	0.0036 (9)	0.0507 (11)	−0.0076 (8)
C13	0.1082 (15)	0.0555 (9)	0.1306 (18)	0.0096 (10)	0.0164 (13)	−0.0239 (10)

Geometric parameters (Å, º) top

C16—C17	1.3417 (16)	C3—C4	1.3424 (17)
C16—C15	1.5061 (15)	C3—C2	1.5052 (18)
C16—C24	1.4823 (17)	C3—C11	1.4854 (18)
C14—O4	1.2201 (14)	O1—C1	1.2132 (16)
C14—O5	1.2981 (13)	O2—H2	0.8200
C14—C15	1.4984 (15)	O2—C1	1.3056 (15)
C17—H17	0.9300	C4—H4	0.9300
C17—C18	1.4639 (17)	C4—C5	1.4651 (17)
O5—H5	0.8200	C5—C10	1.3931 (18)
O6—C24	1.2215 (15)	C5—C6	1.3890 (19)
C15—H15A	0.9700	O3—C11	1.2166 (16)
C15—H15B	0.9700	C2—H2A	0.9700
C18—C19	1.3943 (17)	C2—H2B	0.9700
C18—C23	1.3960 (17)	C2—C1	1.5012 (18)
C24—C25	1.4995 (18)	C11—C12	1.501 (2)
C19—H19	0.9300	C10—H10	0.9300
C19—C20	1.381 (2)	C10—C9	1.380 (2)
C23—H23	0.9300	C9—H9	0.9300
C23—C22	1.386 (2)	C9—C8	1.367 (2)
C25—H25A	0.9600	C6—H6	0.9300
C25—H25B	0.9600	C6—C7	1.382 (2)
C25—H25C	0.9600	C8—C7	1.378 (2)
C22—H22	0.9300	C8—C13	1.511 (2)
C22—C21	1.381 (2)	C7—H7	0.9300
C21—C20	1.379 (2)	C12—H12A	0.9600
C21—C26	1.508 (2)	C12—H12B	0.9600
C20—H20	0.9300	C12—H12C	0.9600
C26—H26A	0.9600	C13—H13A	0.9600
C26—H26B	0.9600	C13—H13B	0.9600
C26—H26C	0.9600	C13—H13C	0.9600

C17—C16—C15	124.87 (11)	C4—C3—C2	125.67 (12)
C17—C16—C24	120.97 (10)	C4—C3—C11	120.59 (12)
C24—C16—C15	114.16 (10)	C11—C3—C2	113.69 (11)
O4—C14—O5	122.88 (10)	C1—O2—H2	109.5
O4—C14—C15	123.19 (10)	C3—C4—H4	115.1
O5—C14—C15	113.93 (10)	C3—C4—C5	129.83 (12)
C16—C17—H17	115.3	C5—C4—H4	115.1
C16—C17—C18	129.44 (11)	C10—C5—C4	117.89 (12)
C18—C17—H17	115.3	C6—C5—C4	124.78 (11)
C14—O5—H5	109.5	C6—C5—C10	117.29 (13)
C16—C15—H15A	108.9	C3—C2—H2A	108.7
C16—C15—H15B	108.9	C3—C2—H2B	108.7
C14—C15—C16	113.50 (9)	H2A—C2—H2B	107.6
C14—C15—H15A	108.9	C1—C2—C3	114.24 (11)
C14—C15—H15B	108.9	C1—C2—H2A	108.7
H15A—C15—H15B	107.7	C1—C2—H2B	108.7
C19—C18—C17	124.22 (11)	O1—C1—O2	123.04 (12)
C19—C18—C23	117.17 (12)	O1—C1—C2	123.22 (11)
C23—C18—C17	118.48 (11)	O2—C1—C2	113.64 (12)
C16—C24—C25	120.56 (11)	C3—C11—C12	120.61 (12)
O6—C24—C16	119.23 (11)	O3—C11—C3	119.53 (13)
O6—C24—C25	120.20 (12)	O3—C11—C12	119.85 (13)
C18—C19—H19	119.4	C5—C10—H10	119.6
C20—C19—C18	121.16 (13)	C9—C10—C5	120.71 (14)
C20—C19—H19	119.4	C9—C10—H10	119.6
C18—C23—H23	119.6	C10—C9—H9	119.0
C22—C23—C18	120.77 (13)	C8—C9—C10	121.94 (14)
C22—C23—H23	119.6	C8—C9—H9	119.0
C24—C25—H25A	109.5	C5—C6—H6	119.6
C24—C25—H25B	109.5	C7—C6—C5	120.82 (14)
C24—C25—H25C	109.5	C7—C6—H6	119.6
H25A—C25—H25B	109.5	C9—C8—C7	117.62 (14)
H25A—C25—H25C	109.5	C9—C8—C13	121.87 (16)
H25B—C25—H25C	109.5	C7—C8—C13	120.51 (17)
C23—C22—H22	119.2	C6—C7—H7	119.2
C21—C22—C23	121.50 (13)	C8—C7—C6	121.57 (15)
C21—C22—H22	119.2	C8—C7—H7	119.2
C22—C21—C26	121.71 (16)	C11—C12—H12A	109.5
C20—C21—C22	117.79 (13)	C11—C12—H12B	109.5
C20—C21—C26	120.49 (16)	C11—C12—H12C	109.5
C19—C20—H20	119.3	H12A—C12—H12B	109.5
C21—C20—C19	121.42 (14)	H12A—C12—H12C	109.5
C21—C20—H20	119.3	H12B—C12—H12C	109.5
C21—C26—H26A	109.5	C8—C13—H13A	109.5
C21—C26—H26B	109.5	C8—C13—H13B	109.5
C21—C26—H26C	109.5	C8—C13—H13C	109.5
H26A—C26—H26B	109.5	H13A—C13—H13B	109.5
H26A—C26—H26C	109.5	H13A—C13—H13C	109.5
H26B—C26—H26C	109.5	H13B—C13—H13C	109.5

C16—C17—C18—C19	−31.0 (2)	C3—C4—C5—C10	−148.97 (15)
C16—C17—C18—C23	153.27 (13)	C3—C4—C5—C6	33.5 (2)
O4—C14—C15—C16	−5.22 (17)	C3—C2—C1—O1	28.9 (2)
C17—C16—C15—C14	101.54 (13)	C3—C2—C1—O2	−154.42 (12)
C17—C16—C24—O6	−178.25 (12)	C4—C3—C2—C1	−101.98 (15)
C17—C16—C24—C25	1.01 (17)	C4—C3—C11—O3	173.44 (14)
C17—C18—C19—C20	−179.59 (14)	C4—C3—C11—C12	−5.2 (2)
C17—C18—C23—C22	−179.83 (12)	C4—C5—C10—C9	179.70 (15)
O5—C14—C15—C16	174.08 (10)	C4—C5—C6—C7	179.85 (16)
C15—C16—C17—C18	−5.48 (19)	C5—C10—C9—C8	1.4 (3)
C15—C16—C24—O6	2.48 (16)	C5—C6—C7—C8	−0.9 (3)
C15—C16—C24—C25	−178.26 (11)	C2—C3—C4—C5	3.4 (2)
C18—C19—C20—C21	0.4 (2)	C2—C3—C11—O3	−9.04 (19)
C18—C23—C22—C21	−1.1 (2)	C2—C3—C11—C12	172.34 (15)
C24—C16—C17—C18	175.34 (11)	C11—C3—C4—C5	−179.38 (13)
C24—C16—C15—C14	−79.23 (12)	C11—C3—C2—C1	80.64 (15)
C19—C18—C23—C22	4.2 (2)	C10—C5—C6—C7	2.4 (3)
C23—C18—C19—C20	−3.8 (2)	C10—C9—C8—C7	0.2 (3)
C23—C22—C21—C20	−2.4 (2)	C10—C9—C8—C13	179.10 (18)
C23—C22—C21—C26	178.96 (15)	C9—C8—C7—C6	−0.4 (3)
C22—C21—C20—C19	2.8 (2)	C6—C5—C10—C9	−2.6 (2)
C26—C21—C20—C19	−178.59 (16)	C13—C8—C7—C6	−179.39 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4ⁱ	0.82	1.82	2.6310 (12)	171
O2—H2···O1ⁱⁱ	0.82	1.85	2.6714 (15)	177

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y+2, −z+1.

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