6,6′-Dimethyl-2,2′-[imidazolidine-1,3-diyl­bis(methyl­ene)]diphenol

Rivera, A.; Nerio, L.S.; Bolte, M.

doi:10.1107/S1600536814002128

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o243

doi:10.1107/S1600536814002128

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6,6′-Dimethyl-2,2′-[imidazolidine-1,3-diylbis(methylene)]diphenol

Augusto Rivera,^a ^* Luz Stella Nerio ^a and Michael Bolte ^b

^aDepartamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogotá, Cra 30 No. 45-03, Bogotá, Colombia, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: ariverau@unal.edu.co

(Received 17 January 2014; accepted 29 January 2014; online 5 February 2014)

In the title compound, C₁₉H₂₄N₂O₂, a di-Mannich base derived from 2-methylphenol and 1,3,6,8-tetraazatricyclo[4.4.1.1^3,8]dodecane, the imidazolidine ring adopts a twist conformation, with a twist about the ring N—C bond [C—N—C—C torsion angle = −44.34 (14)°]. The two 2-hydroxy-3-methylbenzyl groups are located in trans positions with respect to the imidazolidine fragment. The structure displays two intramolecular O—H⋯N hydrogen bonds, which each form an S(6) ring motif. In the crystal, the molecules are linked by weak C—H⋯O interactions with a bifurcated acceptor, forming a three-dimensional network.

CCDC reference: 984201

Related literature

For the original synthesis of the title compound, see: Rivera et al. (1993 ). For related structures, see: Rivera et al. (2011 , 2012a ,b ,c , 2013 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformations, see Cremer & Pople (1975 ). For bifurcated-acceptor hydrogen-bond conformations, see: Desiraju & Steiner (1999 ).

Experimental

Crystal data

C₁₉H₂₄N₂O₂
M_r = 312.40
Monoclinic, P 2₁ /c
a = 12.6271 (11) Å
b = 13.5780 (9) Å
c = 10.1997 (9) Å
β = 107.940 (7)°
V = 1663.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.33 × 0.13 × 0.12 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001 ) T_min = 0.974, T_max = 0.990
16285 measured reflections
3207 independent reflections
2803 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.114
S = 1.07
3207 reflections
219 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.91 (2)	1.90 (2)	2.7115 (16)	146 (2)
O2—H2⋯N2	0.98 (2)	1.70 (2)	2.6202 (16)	155 (2)
C5—H5B⋯O2ⁱ	0.99	2.43	3.4012 (18)	167
C27—H27A⋯O2ⁱⁱ	0.98	2.50	3.1789 (19)	126
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 984201

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814002128/fb2295sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002128/fb2295Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814002128/fb2295Isup3.cml

checkCIF report

Comment top

The title molecule with the atom-numbering scheme is shown in Fig 1. The 2-hydroxy-3-methylbenzyl substituents are arranged in trans configuration with respect to the imidazolidine ring. The imidazolidine ring adopts a twist conformation, with a C1—N1—C2—C3 torsion angle equal to -44.34 (14)° (Cremer & Pople, 1975).

The structure of the title compound shows the presence of two intramolecular O—H···N hydrogen bonds. These bond take part in the S(6) graph set motifs (Bernstein et al., 1995). These motifs occur in the related 2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol compounds (Rivera et al. 2011, 2012a, b, c, 2013), too. The two intramolecular hydrogen bonds are different in their length (Table 1), although both nitrogen atoms are connected to the same atomic species. In the crystal, the molecules are linked to each other by weak C—H···O interactions (Desiraju & Steiner, 1999) C5—H5B···O2ⁱ···H27Aⁱⁱⁱ—C27ⁱⁱⁱ with a bifurcated acceptor O2ⁱ where (i): -x, -y, -z+1; (iii): -x, y-1/2, -z+3/2. (For the hydrogen bonds and interactions, see Table 1.)

Related literature top

For the original synthesis of the title compound, see: Rivera et al. (1993). For related structures, see: Rivera et al. (2011, 2012a,b,c, 2013). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see Cremer & Pople (1975). For bifurcated-acceptor hydrogen-bond terminology, see: Desiraju & Steiner (1999).

Experimental top

For the original synthesis of the title compound, see Rivera et al. (1993). Single crystals in the form of needles that were shorter than 1 mm were obtained by slow evaporation of 0.01 M ethanol solution at room temperature. Melting point: 403-404 K.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The title molecule with the atom-numbering scheme·The displacement ellipsoids are shown at the 50% probability level. The hydrogen bonds are drawn as dashed lines.

6,6'-Dimethyl-2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol top

Crystal data top

C₁₉H₂₄N₂O₂	D_x = 1.247 Mg m⁻³
M_r = 312.40	Melting point = 403–404 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.6271 (11) Å	Cell parameters from 17856 reflections
b = 13.5780 (9) Å	θ = 3.4–26.3°
c = 10.1997 (9) Å	µ = 0.08 mm⁻¹
β = 107.940 (7)°	T = 173 K
V = 1663.7 (2) Å³	Needle, brown
Z = 4	0.33 × 0.13 × 0.12 mm
F(000) = 672

Data collection top

Stoe IPDS II two-circle diffractometer	3207 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	2803 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	R_int = 0.072
ω scans	θ_max = 25.9°, θ_min = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −15→15
T_min = 0.974, T_max = 0.990	k = −16→14
16285 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.053P)² + 0.4801P] whereP = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3207 reflections	Δρ_max = 0.20 e Å⁻³
219 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.017 (3)

Crystal data top

C₁₉H₂₄N₂O₂	V = 1663.7 (2) Å³
M_r = 312.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6271 (11) Å	µ = 0.08 mm⁻¹
b = 13.5780 (9) Å	T = 173 K
c = 10.1997 (9) Å	0.33 × 0.13 × 0.12 mm
β = 107.940 (7)°

Data collection top

Stoe IPDS II two-circle diffractometer	3207 independent reflections
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	2803 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.990	R_int = 0.072
16285 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.20 e Å⁻³
3207 reflections	Δρ_min = −0.17 e Å⁻³
219 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.

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

	x	y	z	U_iso*/U_eq
O1	0.52432 (9)	0.10588 (7)	0.59144 (11)	0.0354 (3)
H1	0.460 (2)	0.1024 (17)	0.519 (2)	0.067 (7)*
O2	−0.00181 (8)	0.17557 (8)	0.53718 (10)	0.0326 (3)
H2	0.047 (2)	0.1533 (18)	0.485 (2)	0.070 (7)*
N1	0.32247 (9)	0.16347 (9)	0.42350 (11)	0.0268 (3)
N2	0.16437 (9)	0.10080 (9)	0.46722 (12)	0.0290 (3)
C1	0.25284 (12)	0.17521 (11)	0.51349 (15)	0.0317 (3)
H1A	0.2207	0.2423	0.5046	0.038*
H1B	0.2969	0.1639	0.6109	0.038*
C2	0.24302 (12)	0.13405 (12)	0.29153 (14)	0.0344 (3)
H2A	0.2812	0.1047	0.2295	0.041*
H2B	0.1970	0.1904	0.2447	0.041*
C3	0.17414 (13)	0.05850 (13)	0.33757 (15)	0.0382 (4)
H3A	0.1000	0.0505	0.2682	0.046*
H3B	0.2122	−0.0062	0.3542	0.046*
C4	0.38508 (12)	0.25297 (11)	0.41628 (15)	0.0306 (3)
H4A	0.3329	0.3089	0.3864	0.037*
H4B	0.4247	0.2440	0.3471	0.037*
C5	0.16693 (12)	0.02503 (11)	0.57129 (15)	0.0314 (3)
H5A	0.2444	0.0013	0.6112	0.038*
H5B	0.1208	−0.0316	0.5255	0.038*
C11	0.46819 (11)	0.27610 (10)	0.55457 (15)	0.0282 (3)
C12	0.53386 (11)	0.20167 (10)	0.63485 (15)	0.0278 (3)
C13	0.61017 (11)	0.22221 (11)	0.76376 (15)	0.0311 (3)
C14	0.62035 (12)	0.31874 (12)	0.80964 (17)	0.0381 (4)
H14	0.6729	0.3341	0.8962	0.046*
C15	0.55590 (13)	0.39346 (12)	0.73245 (19)	0.0424 (4)
H15	0.5636	0.4591	0.7662	0.051*
C16	0.48010 (12)	0.37156 (11)	0.60557 (17)	0.0356 (3)
H16	0.4356	0.4227	0.5526	0.043*
C17	0.67528 (13)	0.14002 (13)	0.85113 (17)	0.0411 (4)
H17A	0.7204	0.1664	0.9402	0.062*
H17B	0.7240	0.1097	0.8042	0.062*
H17C	0.6237	0.0904	0.8659	0.062*
C21	0.12514 (11)	0.06119 (10)	0.68633 (14)	0.0272 (3)
C22	0.04162 (11)	0.13237 (10)	0.66313 (13)	0.0261 (3)
C23	−0.00336 (12)	0.16134 (11)	0.76666 (15)	0.0296 (3)
C24	0.03670 (13)	0.11608 (11)	0.89454 (15)	0.0335 (3)
H24	0.0066	0.1339	0.9658	0.040*
C25	0.11964 (14)	0.04555 (11)	0.92013 (15)	0.0368 (4)
H25	0.1461	0.0155	1.0084	0.044*
C26	0.16402 (12)	0.01877 (11)	0.81681 (15)	0.0330 (3)
H26	0.2216	−0.0291	0.8352	0.040*
C27	−0.09425 (13)	0.23731 (12)	0.73391 (17)	0.0391 (4)
H27A	−0.1177	0.2491	0.8156	0.059*
H27B	−0.1578	0.2136	0.6584	0.059*
H27C	−0.0665	0.2988	0.7063	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0403 (6)	0.0253 (5)	0.0376 (6)	0.0031 (4)	0.0076 (5)	−0.0018 (4)
O2	0.0313 (5)	0.0376 (6)	0.0286 (5)	0.0036 (4)	0.0090 (4)	0.0072 (4)
N1	0.0281 (6)	0.0290 (6)	0.0252 (6)	−0.0013 (5)	0.0109 (5)	−0.0026 (4)
N2	0.0299 (6)	0.0310 (6)	0.0269 (6)	−0.0058 (5)	0.0097 (5)	−0.0056 (5)
C1	0.0318 (7)	0.0343 (8)	0.0332 (7)	−0.0078 (6)	0.0163 (6)	−0.0096 (6)
C2	0.0354 (7)	0.0427 (9)	0.0262 (7)	−0.0025 (6)	0.0111 (6)	−0.0060 (6)
C3	0.0414 (8)	0.0431 (9)	0.0312 (7)	−0.0104 (7)	0.0128 (6)	−0.0131 (6)
C4	0.0300 (7)	0.0311 (7)	0.0329 (7)	0.0001 (6)	0.0130 (6)	0.0059 (6)
C5	0.0308 (7)	0.0277 (7)	0.0350 (8)	−0.0012 (6)	0.0090 (6)	−0.0020 (6)
C11	0.0241 (6)	0.0285 (7)	0.0354 (7)	−0.0028 (5)	0.0141 (6)	0.0021 (6)
C12	0.0257 (6)	0.0264 (7)	0.0345 (7)	−0.0014 (5)	0.0142 (6)	0.0003 (6)
C13	0.0252 (7)	0.0340 (8)	0.0361 (7)	−0.0024 (6)	0.0126 (6)	0.0007 (6)
C14	0.0295 (7)	0.0380 (9)	0.0443 (9)	−0.0083 (6)	0.0076 (6)	−0.0062 (7)
C15	0.0374 (8)	0.0278 (8)	0.0600 (10)	−0.0073 (6)	0.0119 (7)	−0.0095 (7)
C16	0.0311 (7)	0.0254 (7)	0.0507 (9)	−0.0015 (6)	0.0130 (6)	0.0026 (6)
C17	0.0380 (8)	0.0424 (9)	0.0385 (8)	0.0014 (7)	0.0055 (7)	0.0039 (7)
C21	0.0269 (6)	0.0237 (7)	0.0297 (7)	−0.0060 (5)	0.0068 (5)	−0.0015 (5)
C22	0.0260 (6)	0.0247 (7)	0.0261 (6)	−0.0073 (5)	0.0057 (5)	0.0007 (5)
C23	0.0292 (7)	0.0281 (7)	0.0316 (7)	−0.0076 (5)	0.0095 (6)	−0.0041 (5)
C24	0.0418 (8)	0.0325 (8)	0.0280 (7)	−0.0102 (6)	0.0137 (6)	−0.0047 (6)
C25	0.0471 (9)	0.0335 (8)	0.0259 (7)	−0.0064 (7)	0.0053 (6)	0.0045 (6)
C26	0.0333 (7)	0.0275 (7)	0.0333 (7)	−0.0018 (6)	0.0031 (6)	0.0028 (6)
C27	0.0373 (8)	0.0414 (9)	0.0400 (8)	0.0013 (7)	0.0140 (7)	−0.0039 (7)

Geometric parameters (Å, º) top

O1—C12	1.3673 (17)	C12—C13	1.398 (2)
O1—H1	0.91 (2)	C13—C14	1.384 (2)
O2—C22	1.3643 (16)	C13—C17	1.505 (2)
O2—H2	0.98 (2)	C14—C15	1.384 (2)
N1—C1	1.4622 (17)	C14—H14	0.9500
N1—C4	1.4639 (18)	C15—C16	1.384 (2)
N1—C2	1.4650 (18)	C15—H15	0.9500
N2—C5	1.4714 (19)	C16—H16	0.9500
N2—C1	1.4719 (17)	C17—H17A	0.9800
N2—C3	1.4813 (18)	C17—H17B	0.9800
C1—H1A	0.9900	C17—H17C	0.9800
C1—H1B	0.9900	C21—C26	1.393 (2)
C2—C3	1.510 (2)	C21—C22	1.396 (2)
C2—H2A	0.9900	C22—C23	1.401 (2)
C2—H2B	0.9900	C23—C24	1.389 (2)
C3—H3A	0.9900	C23—C27	1.502 (2)
C3—H3B	0.9900	C24—C25	1.383 (2)
C4—C11	1.509 (2)	C24—H24	0.9500
C4—H4A	0.9900	C25—C26	1.386 (2)
C4—H4B	0.9900	C25—H25	0.9500
C5—C21	1.509 (2)	C26—H26	0.9500
C5—H5A	0.9900	C27—H27A	0.9800
C5—H5B	0.9900	C27—H27B	0.9800
C11—C16	1.388 (2)	C27—H27C	0.9800
C11—C12	1.400 (2)

C12—O1—H1	106.2 (15)	C13—C12—C11	121.23 (13)
C22—O2—H2	103.8 (14)	C14—C13—C12	118.17 (14)
C1—N1—C4	112.31 (11)	C14—C13—C17	121.68 (14)
C1—N1—C2	103.44 (11)	C12—C13—C17	120.11 (14)
C4—N1—C2	114.07 (11)	C13—C14—C15	121.64 (15)
C5—N2—C1	113.75 (11)	C13—C14—H14	119.2
C5—N2—C3	112.55 (12)	C15—C14—H14	119.2
C1—N2—C3	106.78 (11)	C16—C15—C14	119.36 (15)
N1—C1—N2	105.53 (11)	C16—C15—H15	120.3
N1—C1—H1A	110.6	C14—C15—H15	120.3
N2—C1—H1A	110.6	C15—C16—C11	121.00 (14)
N1—C1—H1B	110.6	C15—C16—H16	119.5
N2—C1—H1B	110.6	C11—C16—H16	119.5
H1A—C1—H1B	108.8	C13—C17—H17A	109.5
N1—C2—C3	101.34 (11)	C13—C17—H17B	109.5
N1—C2—H2A	111.5	H17A—C17—H17B	109.5
C3—C2—H2A	111.5	C13—C17—H17C	109.5
N1—C2—H2B	111.5	H17A—C17—H17C	109.5
C3—C2—H2B	111.5	H17B—C17—H17C	109.5
H2A—C2—H2B	109.3	C26—C21—C22	118.27 (13)
N2—C3—C2	103.21 (12)	C26—C21—C5	120.23 (13)
N2—C3—H3A	111.1	C22—C21—C5	121.36 (12)
C2—C3—H3A	111.1	O2—C22—C21	121.39 (12)
N2—C3—H3B	111.1	O2—C22—C23	116.77 (12)
C2—C3—H3B	111.1	C21—C22—C23	121.83 (12)
H3A—C3—H3B	109.1	C24—C23—C22	117.96 (14)
N1—C4—C11	110.89 (11)	C24—C23—C27	123.03 (13)
N1—C4—H4A	109.5	C22—C23—C27	118.99 (13)
C11—C4—H4A	109.5	C25—C24—C23	121.28 (14)
N1—C4—H4B	109.5	C25—C24—H24	119.4
C11—C4—H4B	109.5	C23—C24—H24	119.4
H4A—C4—H4B	108.1	C24—C25—C26	119.87 (13)
N2—C5—C21	113.46 (12)	C24—C25—H25	120.1
N2—C5—H5A	108.9	C26—C25—H25	120.1
C21—C5—H5A	108.9	C25—C26—C21	120.79 (14)
N2—C5—H5B	108.9	C25—C26—H26	119.6
C21—C5—H5B	108.9	C21—C26—H26	119.6
H5A—C5—H5B	107.7	C23—C27—H27A	109.5
C16—C11—C12	118.60 (13)	C23—C27—H27B	109.5
C16—C11—C4	120.58 (13)	H27A—C27—H27B	109.5
C12—C11—C4	120.82 (13)	C23—C27—H27C	109.5
O1—C12—C13	117.43 (13)	H27A—C27—H27C	109.5
O1—C12—C11	121.33 (13)	H27B—C27—H27C	109.5

C4—N1—C1—N2	156.96 (11)	C12—C13—C14—C15	1.2 (2)
C2—N1—C1—N2	33.51 (15)	C17—C13—C14—C15	−176.34 (15)
C5—N2—C1—N1	115.88 (13)	C13—C14—C15—C16	−0.7 (2)
C3—N2—C1—N1	−8.89 (15)	C14—C15—C16—C11	−0.3 (2)
C1—N1—C2—C3	−44.34 (14)	C12—C11—C16—C15	0.6 (2)
C4—N1—C2—C3	−166.63 (12)	C4—C11—C16—C15	179.84 (14)
C5—N2—C3—C2	−143.72 (12)	N2—C5—C21—C26	−152.12 (12)
C1—N2—C3—C2	−18.22 (16)	N2—C5—C21—C22	32.45 (18)
N1—C2—C3—N2	38.30 (15)	C26—C21—C22—O2	−178.73 (12)
C1—N1—C4—C11	65.00 (15)	C5—C21—C22—O2	−3.2 (2)
C2—N1—C4—C11	−177.72 (11)	C26—C21—C22—C23	−0.2 (2)
C1—N2—C5—C21	74.79 (14)	C5—C21—C22—C23	175.35 (12)
C3—N2—C5—C21	−163.60 (11)	O2—C22—C23—C24	177.86 (12)
N1—C4—C11—C16	−135.44 (13)	C21—C22—C23—C24	−0.8 (2)
N1—C4—C11—C12	43.76 (17)	O2—C22—C23—C27	−0.48 (19)
C16—C11—C12—O1	178.67 (13)	C21—C22—C23—C27	−179.12 (13)
C4—C11—C12—O1	−0.5 (2)	C22—C23—C24—C25	0.9 (2)
C16—C11—C12—C13	−0.1 (2)	C27—C23—C24—C25	179.21 (14)
C4—C11—C12—C13	−179.28 (12)	C23—C24—C25—C26	−0.2 (2)
O1—C12—C13—C14	−179.60 (13)	C24—C25—C26—C21	−0.8 (2)
C11—C12—C13—C14	−0.8 (2)	C22—C21—C26—C25	1.0 (2)
O1—C12—C13—C17	−2.0 (2)	C5—C21—C26—C25	−174.60 (13)
C11—C12—C13—C17	176.75 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.91 (2)	1.90 (2)	2.7115 (16)	146 (2)
O2—H2···N2	0.98 (2)	1.70 (2)	2.6202 (16)	155 (2)
C5—H5B···O2ⁱ	0.99	2.43	3.4012 (18)	167
C27—H27A···O2ⁱⁱ	0.98	2.50	3.1789 (19)	126

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.91 (2)	1.90 (2)	2.7115 (16)	146 (2)
O2—H2···N2	0.98 (2)	1.70 (2)	2.6202 (16)	155 (2)
C5—H5B···O2ⁱ	0.99	2.43	3.4012 (18)	167.3
C27—H27A···O2ⁱⁱ	0.98	2.50	3.1789 (19)	126.1

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

Acknowledgements

The authors acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work. LSN thanks COLCIENCIAS for a fellowship.

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