Tri­cosane-1,23-diol

In the title compound, C₂₃H₄₈O₂, one of the hydroxy groups adopts a gauche conformation with respect to the hydro­carbon skeleton, whereas the other hydroxy group adopts a trans conformation. The mol­ecules form a layer structure similar to that found in the smectic A phase of liquid crystals. Inter- and intralayer hydrogen bonds are formed in the crystal. These features are similar to those of the homologues with an odd number of C atoms. The calculated density, however, deviates from that predicted by a relation between the density and the number of C atoms in alkane-α,ω-diols with an odd number of C atoms.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.192
• Data-to-parameter ratio = 10.7

checkCIF results

No syntax errors found

Structure: I
------------

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           70.60
         From the CIF: _reflns_number_total               2538
         Count of symmetry unique reflns         2653
         Completeness (_total/calc)             95.67%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

S1. Comment

Normal long-chain aliphatic compounds have been investigated recently as models for smectic liquid crystals. Phase-transition phenomena in alkane-α,ω-diols containing 13–24 C atoms have been studied (Ogawa & Nakamura, 1999). It was defined that alkane-α,ω-diols containing 13–24 C atoms, except for the diol containing 14 C atoms, had a rotator phase in which molecules were assured greater motional freedom, as well as that observed in liquid crystals. In addition, it was reported that the analogous compounds with two hydroxy groups at one or both chain ends had the smectic phase of liquid crystals (Hentrich et al., 1994). Therefore, the crystal data of alkane-α,ω-diols are important in order to explain of the phase-transition behavior.

The crystal structures of 11 alkane-α,ω-diols containing 10–19 and 21 C atoms have been investigated by Nakamura and co-workers: 1,10-decanediol (Nakamura & Sato, 1999a), 1,11-undecanediol (Nakamura, Setodoi & Ikeya, 1999), 1,12-dodecanediol (Nakamura & Setodoi, 1997), 1,13-tridecanediol (Nakamura, Tanihara & Takayama, 1997), 1,14-tetradecanediol (Nakamura & Sato, 1999b), 1,15-pentadecanediol (Nakamura, Uno, Watanabe et al., 2000), 1,16-hexadecanediol (Nakamura & Yamamoto, 1994), 1,17-heptadecanediol (Nakamura et al., 2001a), octadecane-1,18-diol (Nakamura & Watanabe, 2001), nonadecane-1,19-diol (Nakamura et al., 2001b) and 1,21-henicosanediol (Nakamura, Uno & Ogawa, 2000). The structures obtained divided into two groups, one series has an even number of C atoms and the other series has an odd number of C atoms. In this paper, the crystal structure of tricosane-1,23-diol, (I), is described and compared with the other alkane-α,ω-diols.

Fig. 1 shows the molecular structure of (I). The terminal torsion angles O1—C1—C2—C3 and O2—C23—C22—C21 are 63.9 (4) and -179.6 (2)°, respectively. This means that the former has a gauche conformation and the latter a trans conformation. Fig. 2 shows the projection of the crystal structure of (I) along the c axis. The long axis of molecules is normal to the ac plane, and the molecules form layers with a thickness of b/2. The packing is similar to that in the smectic A phase of liquid crystals. The molecules also form two different types of hydrogen bond, i.e. interlayer and intralayer. The donor–acceptor distances of the inter- and intralayer hydrogen bonds are 2.711 (2) and 2.778 (4) Å, respectively. These features are similar to those of other alkane-α,ω-diols with an odd number of C atoms.

The calculated densities of the odd-numbered alkane-α,ω-diols containing 11–21 C atoms were 1.050, 1.045, 1.041, 1.037, 1.034 and 1.029 Mg m^-3, respectively. As the X-ray structure analyses were carried out at nearly the same temperature, the density of tricosane-1,23-diol was estimated to be less than 1.029 Mg m^-3. However, it is 1.031 Mg m^-3. This fact shows that it is far from the tendency to decrease slightly with increasing chain length in the odd-numbered alkane-α,ω-diols. This feature is in harmony with that observed in the relation between the crystal-rotator phase transition temperature (T_t) and number of C atoms in the compounds. The T_t of tricosane-1,23-diol is a little higher than the T_t predicted from the relation (Ogawa & Nakamura, 1999).

S2. Experimental

The title compound was synthesized as described previously (Ogawa & Nakamura, 1999). The diacid was obtained from short-chain diacids by a ketene dimerization synthesis (Blomquist et al., 1952) and was converted to the methyl ester by conventional procedures. The pure compound was obtained through fractional distillation and recrystallization, and the purity was 99.9% or higher. The single-crystal used for the analysis was grown by slow evaporation from a solution containing a mixture of methanol, ethyl acetate and n-heptane (1:1:1).

S3. Refinement

The measured fraction (θ_max= 70.6°) of 0.952 is relatively low, which is due to the blind region of χ-90 setting. The absolute structure was tentatively assigned. The methylene-H atoms were located at idealized positions, and were allowed to ride on the parent C atoms (C—H = 0.95 Å). The hydroxy-H atoms were located from a difference Fourier map, and were allowed to refine isotropically for the final refinements [O—H = 0.75 (3) and 0.82 (3) Å]. The H-atom isotropic displacement parameters were set to be 1.2U_eq of the parent atom.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2000); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

Figures

	Fig. 1. An ORTEPII (Johnson, 1976) view of the molecule of (I) showing the crystallographic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The projection of the crystal structure of (I) along the c axis. Dotted lines indicate the hydrogen bonding.

(I)

Crystal data

C23H48O2	Dx = 1.031 Mg m^−3
Mr = 356.61	Melting point: 380.65 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 19 reflections
a = 7.230 (6) Å	θ = 9.8–13.3°
b = 63.045 (5) Å	µ = 0.47 mm^−1
c = 5.041 (4) Å	T = 296 K
V = 2298 (2) Å^3	Plate, colorless
Z = 4	0.60 × 0.30 × 0.03 mm
F(000) = 808.00

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.009
ω scans	θmax = 70.6°
Absorption correction: ψ scan (North et al., 1968)	h = −2→8
Tmin = 0.851, Tmax = 0.986	k = 0→77
4062 measured reflections	l = −1→6
2538 independent reflections	3 standard reflections every 150 reflections
1692 reflections with F^2 > 2.0σ(F^2)	intensity decay: 3.3%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + {0.09[Max(Fo^2,0) + 2Fc^2]/3}^2]
R[F^2 > 2σ(F^2)] = 0.044	(Δ/σ)max < 0.001
wR(F^2) = 0.192	Δρmax = 0.25 e Å^−3
S = 1.41	Δρmin = −0.20 e Å^−3
2491 reflections	Extinction correction: Zachariasen (1967) type 2 Gaussian isotropic
233 parameters	Extinction coefficient: 0.047 (7)
H atoms treated by a mixture of independent and constrained refinement

Special details

Refinement. Refinement using reflections with F² > -3.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.5594 (3)	0.26634 (2)	0.1396 (4)	0.0634 (5)
O2	0.5611 (3)	0.72932 (2)	0.5722 (5)	0.0723 (6)
C1	0.5020 (5)	0.26853 (3)	0.4081 (6)	0.0645 (9)
C2	0.5571 (5)	0.28954 (3)	0.5269 (6)	0.0591 (7)
C3	0.4678 (4)	0.30871 (3)	0.3965 (5)	0.0496 (6)
C4	0.5407 (4)	0.32939 (3)	0.5116 (5)	0.0492 (6)
C5	0.4584 (4)	0.34919 (3)	0.3868 (5)	0.0476 (6)
C6	0.5383 (4)	0.36961 (3)	0.4993 (5)	0.0482 (6)
C7	0.4578 (4)	0.38961 (3)	0.3753 (5)	0.0480 (6)
C8	0.5395 (4)	0.40988 (3)	0.4896 (5)	0.0482 (6)
C9	0.4584 (4)	0.42998 (3)	0.3685 (6)	0.0479 (6)
C10	0.5400 (4)	0.45016 (3)	0.4843 (6)	0.0482 (6)
C11	0.4598 (4)	0.47035 (3)	0.3660 (5)	0.0473 (6)
C12	0.5404 (3)	0.49054 (3)	0.4819 (5)	0.0478 (6)
C13	0.4594 (3)	0.51073 (3)	0.3648 (5)	0.0477 (6)
C14	0.5403 (4)	0.53087 (3)	0.4819 (6)	0.0485 (6)
C15	0.4592 (4)	0.55112 (3)	0.3662 (6)	0.0478 (6)
C16	0.5401 (4)	0.57121 (3)	0.4862 (6)	0.0486 (6)
C17	0.4590 (4)	0.59148 (3)	0.3711 (5)	0.0476 (6)
C18	0.5389 (4)	0.61155 (3)	0.4932 (5)	0.0484 (6)
C19	0.4573 (4)	0.63195 (3)	0.3821 (5)	0.0483 (6)
C20	0.5390 (4)	0.65180 (3)	0.5079 (6)	0.0495 (7)
C21	0.4588 (4)	0.67246 (3)	0.4024 (5)	0.0492 (6)
C22	0.5445 (4)	0.69177 (3)	0.5339 (6)	0.0522 (7)
C23	0.4687 (4)	0.71259 (3)	0.4350 (6)	0.0563 (7)
H1a	0.3711	0.2673	0.4154	0.0774*
H1b	0.5565	0.2575	0.5096	0.0774*
H1o	0.672 (5)	0.2681 (5)	0.138 (7)	0.0760*
H2a	0.5235	0.2895	0.7091	0.0709*
H2b	0.6875	0.2909	0.5116	0.0709*
H2o	0.522 (5)	0.7395 (5)	0.519 (8)	0.0868*
H3a	0.4934	0.3084	0.2118	0.0595*
H3b	0.3379	0.3081	0.4237	0.0595*
H4a	0.5137	0.3296	0.6959	0.0590*
H4b	0.6709	0.3297	0.4866	0.0590*
H5a	0.4819	0.3488	0.2014	0.0571*
H5b	0.3287	0.3491	0.4167	0.0571*
H6a	0.5143	0.3699	0.6845	0.0579*
H6b	0.6681	0.3696	0.4700	0.0579*
H7a	0.4816	0.3893	0.1900	0.0576*
H7b	0.3281	0.3897	0.4049	0.0576*
H8a	0.5168	0.4101	0.6752	0.0578*
H8b	0.6691	0.4098	0.4585	0.0578*
H9a	0.4816	0.4298	0.1830	0.0575*
H9b	0.3287	0.4300	0.3989	0.0575*
H10a	0.5172	0.4502	0.6699	0.0578*
H10b	0.6696	0.4501	0.4534	0.0578*
H11a	0.4830	0.4703	0.1806	0.0567*
H11b	0.3302	0.4704	0.3964	0.0567*
H12a	0.5179	0.4906	0.6676	0.0574*
H12b	0.6700	0.4905	0.4506	0.0574*
H13a	0.4822	0.5107	0.1792	0.0572*
H13b	0.3298	0.5107	0.3958	0.0572*
H14a	0.5179	0.5308	0.6676	0.0582*
H14b	0.6698	0.5309	0.4503	0.0582*
H15a	0.4824	0.5512	0.1807	0.0573*
H15b	0.3296	0.5511	0.3966	0.0573*
H16a	0.5171	0.5711	0.6717	0.0583*
H16b	0.6697	0.5712	0.4555	0.0583*
H17a	0.4831	0.5917	0.1858	0.0571*
H17b	0.3293	0.5914	0.4003	0.0571*
H18a	0.5162	0.6112	0.6787	0.0581*
H18b	0.6684	0.6117	0.4621	0.0581*
H19a	0.4803	0.6324	0.1966	0.0580*
H19b	0.3277	0.6319	0.4128	0.0580*
H20a	0.5170	0.6512	0.6935	0.0594*
H20b	0.6685	0.6518	0.4758	0.0594*
H21a	0.4809	0.6732	0.2168	0.0591*
H21b	0.3293	0.6726	0.4345	0.0591*
H22a	0.5224	0.6909	0.7193	0.0627*
H22b	0.6739	0.6915	0.5016	0.0627*
H23a	0.3396	0.7133	0.4690	0.0675*
H23b	0.4901	0.7138	0.2498	0.0675*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.089 (1)	0.0372 (7)	0.064 (1)	−0.0041 (9)	0.005 (1)	−0.0043 (8)
O2	0.091 (1)	0.0302 (7)	0.096 (2)	0.0020 (9)	−0.022 (2)	−0.0011 (8)
C1	0.095 (2)	0.034 (1)	0.065 (2)	−0.004 (1)	0.013 (2)	0.010 (1)
C2	0.087 (2)	0.036 (1)	0.054 (1)	0.002 (1)	−0.002 (2)	0.0023 (10)
C3	0.061 (2)	0.0339 (10)	0.054 (1)	0.001 (1)	0.003 (2)	−0.0012 (9)
C4	0.057 (2)	0.0341 (10)	0.056 (1)	0.000 (1)	−0.002 (2)	−0.0029 (9)
C5	0.053 (1)	0.0328 (9)	0.057 (1)	0.0002 (10)	0.001 (2)	−0.0024 (10)
C6	0.054 (1)	0.0324 (10)	0.059 (1)	−0.0019 (10)	0.000 (2)	−0.0046 (9)
C7	0.051 (1)	0.0323 (9)	0.060 (1)	−0.0015 (10)	0.000 (2)	−0.0011 (10)
C8	0.053 (1)	0.0317 (10)	0.060 (1)	−0.0015 (10)	−0.003 (2)	−0.0016 (9)
C9	0.052 (1)	0.0313 (9)	0.060 (1)	−0.0003 (10)	−0.001 (2)	−0.0015 (9)
C10	0.052 (1)	0.0312 (10)	0.062 (1)	0.000 (1)	−0.002 (2)	−0.0022 (9)
C11	0.050 (1)	0.0320 (10)	0.060 (1)	0.0004 (10)	−0.003 (2)	−0.0010 (10)
C12	0.052 (1)	0.0317 (10)	0.060 (1)	−0.001 (1)	0.000 (1)	0.0002 (9)
C13	0.051 (1)	0.0309 (9)	0.061 (1)	0.000 (1)	−0.002 (1)	−0.0011 (10)
C14	0.053 (1)	0.0310 (10)	0.062 (1)	−0.001 (1)	0.000 (2)	0.0003 (9)
C15	0.052 (1)	0.0313 (9)	0.060 (1)	0.0014 (10)	−0.002 (2)	−0.0013 (9)
C16	0.053 (1)	0.0300 (10)	0.063 (1)	−0.0007 (10)	−0.002 (2)	−0.0003 (9)
C17	0.051 (1)	0.0314 (10)	0.060 (1)	0.0006 (9)	−0.003 (2)	0.0001 (9)
C18	0.054 (1)	0.0304 (10)	0.061 (1)	−0.0016 (10)	−0.002 (2)	0.0000 (9)
C19	0.053 (1)	0.0312 (9)	0.060 (1)	0.0020 (10)	−0.002 (2)	0.0008 (10)
C20	0.054 (1)	0.0317 (10)	0.063 (1)	−0.001 (1)	−0.004 (2)	0.0008 (9)
C21	0.055 (1)	0.0328 (9)	0.060 (1)	0.003 (1)	−0.003 (2)	0.0026 (10)
C22	0.060 (2)	0.0304 (10)	0.067 (1)	−0.001 (1)	−0.002 (2)	0.0022 (9)
C23	0.065 (2)	0.0309 (9)	0.073 (2)	0.003 (1)	−0.001 (2)	0.0012 (10)

Geometric parameters (Å, º)

O1—C1	1.423 (4)	C6—H6a	0.95
O2—C23	1.427 (3)	C6—H6b	0.95
C1—C2	1.507 (3)	C7—H7a	0.95
C2—C3	1.520 (3)	C7—H7b	0.95
C3—C4	1.521 (3)	C8—H8a	0.95
C4—C5	1.519 (3)	C8—H8b	0.95
C5—C6	1.521 (3)	C9—H9a	0.95
C6—C7	1.523 (3)	C9—H9b	0.95
C7—C8	1.521 (3)	C10—H10a	0.95
C8—C9	1.524 (3)	C10—H10b	0.95
C9—C10	1.519 (3)	C11—H11a	0.95
C10—C11	1.520 (3)	C11—H11b	0.95
C11—C12	1.517 (3)	C12—H12a	0.95
C12—C13	1.520 (3)	C12—H12b	0.95
C13—C14	1.518 (3)	C13—H13a	0.95
C14—C15	1.521 (3)	C13—H13b	0.95
C15—C16	1.521 (3)	C14—H14a	0.95
C16—C17	1.521 (3)	C14—H14b	0.95
C17—C18	1.521 (3)	C15—H15a	0.95
C18—C19	1.522 (3)	C15—H15b	0.95
C19—C20	1.522 (3)	C16—H16a	0.95
C20—C21	1.522 (3)	C16—H16b	0.95
C21—C22	1.519 (3)	C17—H17a	0.95
C22—C23	1.507 (3)	C17—H17b	0.95
O1—H1o	0.82 (3)	C18—H18a	0.95
O2—H2o	0.75 (3)	C18—H18b	0.95
C1—H1a	0.95	C19—H19a	0.95
C1—H1b	0.95	C19—H19b	0.95
C2—H2a	0.95	C20—H20a	0.95
C2—H2b	0.95	C20—H20b	0.95
C3—H3a	0.95	C21—H21a	0.95
C3—H3b	0.95	C21—H21b	0.95
C4—H4a	0.95	C22—H22a	0.95
C4—H4b	0.95	C22—H22b	0.95
C5—H5a	0.95	C23—H23a	0.95
C5—H5b	0.95	C23—H23b	0.95
O1—C1—C2	112.7 (2)	C9—C10—H10a	108.4
C1—C2—C3	114.5 (2)	C9—C10—H10b	108.4
C2—C3—C4	111.7 (2)	C11—C10—H10a	108.4
C3—C4—C5	114.2 (2)	C11—C10—H10b	108.4
C4—C5—C6	113.1 (2)	H10a—C10—H10b	109.5
C5—C6—C7	113.7 (2)	C10—C11—H11a	108.4
C6—C7—C8	113.1 (2)	C10—C11—H11b	108.4
C7—C8—C9	113.4 (2)	C12—C11—H11a	108.4
C8—C9—C10	113.1 (2)	C12—C11—H11b	108.4
C9—C10—C11	113.7 (2)	H11a—C11—H11b	109.5
C10—C11—C12	113.9 (2)	C11—C12—H12a	108.4
C11—C12—C13	113.9 (2)	C11—C12—H12b	108.4
C12—C13—C14	113.6 (2)	C13—C12—H12a	108.4
C13—C14—C15	113.9 (2)	C13—C12—H12b	108.4
C14—C15—C16	113.5 (2)	H12a—C12—H12b	109.5
C15—C16—C17	113.6 (2)	C12—C13—H13a	108.4
C16—C17—C18	113.5 (2)	C12—C13—H13b	108.4
C17—C18—C19	114.0 (2)	C14—C13—H13a	108.4
C18—C19—C20	113.0 (2)	C14—C13—H13b	108.4
C19—C20—C21	114.2 (2)	H13a—C13—H13b	109.5
C20—C21—C22	112.2 (2)	C13—C14—H14a	108.4
C21—C22—C23	113.9 (2)	C13—C14—H14b	108.4
O2—C23—C22	108.2 (2)	C15—C14—H14a	108.4
C1—O1—H1o	106 (2)	C15—C14—H14b	108.4
C23—O2—H2o	106 (2)	H14a—C14—H14b	109.5
O1—C1—H1a	108.7	C14—C15—H15a	108.5
O1—C1—H1b	108.7	C14—C15—H15b	108.5
C2—C1—H1a	108.7	C16—C15—H15a	108.5
C2—C1—H1b	108.7	C16—C15—H15b	108.5
H1a—C1—H1b	109.5	H15a—C15—H15b	109.5
C1—C2—H2a	108.2	C15—C16—H16a	108.4
C1—C2—H2b	108.2	C15—C16—H16b	108.4
C3—C2—H2a	108.2	C17—C16—H16a	108.4
C3—C2—H2b	108.2	C17—C16—H16b	108.4
H2a—C2—H2b	109.5	H16a—C16—H16b	109.5
C2—C3—H3a	108.9	C16—C17—H17a	108.5
C2—C3—H3b	108.9	C16—C17—H17b	108.5
C4—C3—H3a	108.9	C18—C17—H17a	108.5
C4—C3—H3b	108.9	C18—C17—H17b	108.5
H3a—C3—H3b	109.5	H17a—C17—H17b	109.5
C3—C4—H4a	108.3	C17—C18—H18a	108.3
C3—C4—H4b	108.3	C17—C18—H18b	108.3
C5—C4—H4a	108.3	C19—C18—H18a	108.3
C5—C4—H4b	108.3	C19—C18—H18b	108.3
H4a—C4—H4b	109.5	H18a—C18—H18b	109.5
C4—C5—H5a	108.6	C18—C19—H19a	108.6
C4—C5—H5b	108.6	C18—C19—H19b	108.6
C6—C5—H5a	108.6	C20—C19—H19a	108.6
C6—C5—H5b	108.6	C20—C19—H19b	108.6
H5a—C5—H5b	109.5	H19a—C19—H19b	109.5
C5—C6—H6a	108.4	C19—C20—H20a	108.3
C5—C6—H6b	108.4	C19—C20—H20b	108.3
C7—C6—H6a	108.4	C21—C20—H20a	108.3
C7—C6—H6b	108.4	C21—C20—H20b	108.3
H6a—C6—H6b	109.5	H20a—C20—H20b	109.5
C6—C7—H7a	108.6	C20—C21—H21a	108.8
C6—C7—H7b	108.6	C20—C21—H21b	108.8
C8—C7—H7a	108.6	C22—C21—H21a	108.8
C8—C7—H7b	108.6	C22—C21—H21b	108.8
H7a—C7—H7b	109.5	H21a—C21—H21b	109.5
C7—C8—H8a	108.5	C21—C22—H22a	108.3
C7—C8—H8b	108.5	C21—C22—H22b	108.4
C9—C8—H8a	108.5	C23—C22—H22a	108.3
C9—C8—H8b	108.5	C23—C22—H22b	108.3
H8a—C8—H8b	109.5	H22a—C22—H22b	109.5
C8—C9—H9a	108.6	O2—C23—H23a	109.8
C8—C9—H9b	108.5	O2—C23—H23b	109.8
C10—C9—H9a	108.6	C22—C23—H23a	109.8
C10—C9—H9b	108.5	C22—C23—H23b	109.8
H9a—C9—H9b	109.5	H23a—C23—H23b	109.5
O1—C1—C2—C3	63.9 (4)	C11—C12—C13—C14	179.9 (2)
O2—C23—C22—C21	−179.6 (2)	C12—C13—C14—C15	−179.8 (2)
C1—C2—C3—C4	−175.6 (2)	C13—C14—C15—C16	179.6 (2)
C2—C3—C4—C5	179.2 (2)	C14—C15—C16—C17	−179.9 (2)
C3—C4—C5—C6	−178.1 (2)	C15—C16—C17—C18	179.5 (2)
C4—C5—C6—C7	179.7 (2)	C16—C17—C18—C19	−179.3 (2)
C5—C6—C7—C8	−179.9 (2)	C17—C18—C19—C20	179.8 (2)
C6—C7—C8—C9	−179.4 (2)	C18—C19—C20—C21	−179.5 (2)
C7—C8—C9—C10	179.7 (2)	C19—C20—C21—C22	180.0 (2)
C8—C9—C10—C11	−179.8 (2)	C20—C21—C22—C23	−180.0 (2)
C9—C10—C11—C12	179.8 (2)	C20—C21—C22—C23	−180.0 (2)
C10—C11—C12—C13	−179.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2^i	0.82 (3)	1.96 (3)	2.778 (2)	170 (3)
O2—H2o···O1^ii	0.75 (3)	1.96 (3)	2.711 (2)	174 (3)

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+1/2.