2,2′-[(4-Methyl-2-phenyl­imidazolidine-1,3-di­yl)bis­(methyl­ene)]diphenol

Rivera, A.; Cárdenas, L.; Ríos-Motta, J.; Eigner, V.; Dušek, M.

doi:10.1107/S1600536813017893

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1198

doi:10.1107/S1600536813017893

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2,2′-[(4-Methyl-2-phenylimidazolidine-1,3-diyl)bis(methylene)]diphenol

Augusto Rivera,^a ^* Lorena Cárdenas,^a Jaime Ríos-Motta,^a Václav Eigner ^b,^c and Michal Dušek ^c

^aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No.45-03, Bogotá, Código Postal 111321, Colombia, ^bDepartment of Solid State Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague, Czech Republic, and ^cInstitute of Physics AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic
^*Correspondence e-mail: ariverau@unal.edu.co

(Received 27 June 2013; accepted 28 June 2013; online 3 July 2013)

The methyl-substituted imidazolidine ring of the title compound, C₂₄H₂₆N₂O₂, adopts an envelope conformation with the N atom adjacent to the methylene group as the flap. The methyl–ethylene fragment in this ring is disordered over two positions with an occupancy ratio of 0.899 (4):0.101 (4). The hydroxybenzyl groups are inclined at 71.57 (15) and 69.97 (19)° to the mean plane of major disorder component of the heterocyclic ring with an interplanar angle between the two hydroxybenzyl groups of 66.00 (5)°. The phenyl substituent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 75.60 (12)°. This conformation is stabilized by two intramolecular O—H⋯N bonds, which generate S(6) ring motifs.

Related literature

For related structures, see: Rivera et al. (2012a ,b ). For the synthesis of the precursor, see: Rivera et al. (2013 ). For bond-length data, see: Allen et al. (1987 ). For puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₄H₂₆N₂O₂
M_r = 374.5
Monoclinic, P 2₁ /c
a = 16.8974 (8) Å
b = 9.4893 (5) Å
c = 12.5287 (6) Å
β = 92.928 (4)°
V = 2006.29 (17) Å³
Z = 4
Cu Kα radiation
μ = 0.62 mm⁻¹
T = 120 K
0.35 × 0.25 × 0.09 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ) T_min = 0.886, T_max = 0.952
8259 measured reflections
3491 independent reflections
2704 reflections with I > 3σ(I)
R_int = 0.03

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.113
S = 1.51
3491 reflections
276 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o1⋯N9	0.98 (2)	1.88 (2)	2.7569 (18)	147.7 (19)
O19—H1o19⋯N11	1.00 (2)	1.79 (2)	2.709 (2)	152 (2)

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis 2007 ); program(s) used to refine structure: JANA2006 (Petříček et al. 2006 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813017893/sj5339sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813017893/sj5339Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813017893/sj5339Isup3.cml

checkCIF report

Comment top

We have recently synthesized for the first time a series of tetrasubstituted imidazolidines by the reaction of N,N'-dibenzylpropane-1,2-diamine with substituted benzaldehydes, and we have provided evidence that they display intramolecular O—H···N hydrogen bonds (Rivera et al., 2013). In this article, we further advance these investigations by presenting the crystal structure of the title compound.

In the title compound, C₂₄H₂₆N₂O_2, the methyl-substituted imidazolidine ring exhibits molecular disorder over two orientations, with a refined occupancy ratio of 0.899 (4):0.101 (4) for atoms (C26, C27, C28):(C26', C27', C28'). For the major component, the imidazolidine ring (N9/C10/N11/C26/C27) adopts an envelope conformation with atom N11 as the flap: puckering parameters (Cremer & Pople, 1975) being Q2 = 0.4429 (19) Å and Φ = 75.0 (2)°. The bond lengths (Allen et al., 1987) and angles are close to standard values. Within the imidazolidine ring, bond distances and angles are comparable to those found in related structures (Rivera et al., 2012a,b). The C2—O1 and C18—O19 bond lengths are 1.374 (2) and 1.369 (2) Å, respectively, which are comparable to other C—O bond lengths in di-Mannich bases reported by us (Rivera et al., 2012a,b). The hydroxybenzyl groups makes an angle of 71.57 (15)° and 69.97 (19)° with the mean plane of heterocyclic ring defined by N9,C10,C26 and C27. With reference to this plane, the phenyl ring is almost perpendicular with a dihedral angle of 75.60 (12)°. The interplanar angle between the two hydroxybenzyl groups is 66.00 (5)°.

Single-crystal X-ray diffraction analysis reveals the existence of intramolecular O—H··· N hydrogen-bonding interactions between the two N atoms of the imidazolidine ring and the hydroxyl groups in the aromatic rings with S(6) set graph motifs (Bernstein et al. 1995) (Table 1). However, the two observed intramolecular hydrogen bond distances were different (Table 1). It is then surprising to observe the difference in O···N distances between O1···N9 [O···N = 2.757 (2) Å] and O19···N11[O···N = 2.709 (2) Å], which are longer than those observed in a related structure (Rivera et al., 2012a). Because the length of hydrogen bonds depends on bond strength, these results indicated that the nitrogen atoms in the title compound are weaker hydrogen bond acceptors than the nitrogen in related structure (Rivera et al., 2012a). This fact can be explained by the presence of the aryl group at the aminal carbon, where the imidazolidine ring adopts a conformation that causes an increase in unfavorable through-space interactions between the two nitrogen lone pairs. Thus, one of the possible consequences of these structural features is the reduction in electronic density around the nitrogen atoms.

Related literature top

For related structures, see: Rivera et al. (2012a,b). For the synthesis of the precursor, see: Rivera et al. (2013). For bond-length data, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995).

Experimental top

For the originally reported synthesis, see: Rivera et al. (2013). The title compound (I) were recrystallized from ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis 2007); program(s) used to refine structure: JANA2006 (Petříček et al. 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al. 2006).

Figures top

Fig. 1. A perspective view of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are drawn as dashed lines and only the major disorder component of the disordered section of the imidazolidine ring is shown.

2,2'-[(4-Methyl-2-phenylimidazolidine-1,3-diyl)bis(methylene)]diphenol top

Crystal data top

C₂₄H₂₆N₂O₂	F(000) = 800
M_r = 374.5	D_x = 1.239 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ycb	Cell parameters from 3676 reflections
a = 16.8974 (8) Å	θ = 3.5–66.9°
b = 9.4893 (5) Å	µ = 0.62 mm⁻¹
c = 12.5287 (6) Å	T = 120 K
β = 92.928 (4)°	Polygon shape, colorless
V = 2006.29 (17) Å³	0.35 × 0.25 × 0.09 mm
Z = 4

Data collection top

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3491 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2704 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.03
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.0°, θ_min = 5.2°
ω scans	h = −16→19
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −11→11
T_min = 0.886, T_max = 0.952	l = −14→12
8259 measured reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.042	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0016I²)
wR(F²) = 0.113	(Δ/σ)_max = 0.049
S = 1.51	Δρ_max = 0.25 e Å⁻³
3491 reflections	Δρ_min = −0.18 e Å⁻³
276 parameters	Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)
5 restraints	Extinction coefficient: 3200 (500)
151 constraints

Crystal data top

C₂₄H₂₆N₂O₂	V = 2006.29 (17) Å³
M_r = 374.5	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 16.8974 (8) Å	µ = 0.62 mm⁻¹
b = 9.4893 (5) Å	T = 120 K
c = 12.5287 (6) Å	0.35 × 0.25 × 0.09 mm
β = 92.928 (4)°

Data collection top

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3491 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	2704 reflections with I > 3σ(I)
T_min = 0.886, T_max = 0.952	R_int = 0.03
8259 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	5 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.51	Δρ_max = 0.25 e Å⁻³
3491 reflections	Δρ_min = −0.18 e Å⁻³
276 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.10968 (7)	0.77621 (13)	0.14452 (10)	0.0335 (4)
O19	0.40788 (9)	1.04207 (16)	0.27300 (11)	0.0460 (5)
N11	0.28125 (8)	0.99956 (14)	0.39327 (11)	0.0262 (4)
N9	0.16113 (8)	0.91720 (14)	0.32755 (11)	0.0262 (4)
C3	−0.01906 (11)	0.84850 (19)	0.08234 (15)	0.0323 (5)
C17	0.49554 (10)	1.2217 (2)	0.33593 (15)	0.0335 (6)
C22	0.33481 (10)	0.58293 (19)	0.28115 (14)	0.0303 (5)
C2	0.03749 (10)	0.83400 (18)	0.16509 (14)	0.0282 (5)
C18	0.43614 (10)	1.12529 (19)	0.35565 (13)	0.0301 (5)
C21	0.29810 (10)	0.71116 (18)	0.29487 (13)	0.0277 (5)
C4	−0.09159 (11)	0.91012 (19)	0.10146 (15)	0.0355 (6)
C16	0.52487 (10)	1.3093 (2)	0.41629 (15)	0.0360 (6)
C13	0.40514 (10)	1.11650 (18)	0.45702 (13)	0.0276 (5)
C25	0.26334 (10)	0.63967 (18)	0.46963 (13)	0.0274 (5)
C10	0.22524 (10)	0.88368 (17)	0.40711 (13)	0.0261 (5)
C20	0.26239 (9)	0.74138 (17)	0.39014 (12)	0.0241 (5)
C12	0.34266 (11)	1.00921 (19)	0.47984 (13)	0.0311 (5)
C14	0.43528 (11)	1.2068 (2)	0.53588 (14)	0.0340 (6)
C7	0.02229 (10)	0.87866 (17)	0.26891 (13)	0.0275 (5)
C28	0.17720 (14)	1.1089 (2)	0.19419 (16)	0.0394 (7)	0.899 (4)
C23	0.33604 (10)	0.48228 (19)	0.36133 (14)	0.0315 (5)
C24	0.29998 (10)	0.51088 (19)	0.45540 (14)	0.0310 (5)
C8	0.08435 (10)	0.86041 (19)	0.35794 (13)	0.0311 (5)
C6	−0.05061 (10)	0.94177 (19)	0.28506 (15)	0.0333 (6)
C5	−0.10736 (11)	0.95685 (19)	0.20251 (15)	0.0357 (6)
C27	0.16255 (12)	1.07345 (19)	0.30988 (16)	0.0280 (6)	0.899 (4)
C26	0.22944 (12)	1.1238 (2)	0.38684 (17)	0.0288 (6)	0.899 (4)
C26'	0.1443 (9)	1.0661 (5)	0.3488 (14)	0.0280 (6)	0.101 (4)
C27'	0.2300 (7)	1.1160 (12)	0.3475 (10)	0.0288 (6)	0.101 (4)
C15	0.49529 (11)	1.3021 (2)	0.51673 (15)	0.0383 (6)
H1c3	−0.008331	0.816175	0.011928	0.0387*
H1c17	0.516222	1.227294	0.266103	0.0402*
H1c22	0.359666	0.563345	0.21556	0.0364*
H1c21	0.29715	0.779845	0.238562	0.0333*
H1c4	−0.130988	0.920237	0.044006	0.0426*
H1c16	0.566013	1.375547	0.402306	0.0432*
H1c25	0.238354	0.658669	0.535225	0.0329*
H1c10	0.207032	0.876559	0.478241	0.0313*
H1c12	0.367021	0.918641	0.490924	0.0373*
H2c12	0.31869	1.033102	0.545288	0.0373*
H1c14	0.414141	1.203482	0.60552	0.0408*
H1c28	0.177434	1.20937	0.185208	0.0473*	0.899 (4)
H2c28	0.227476	1.071195	0.175972	0.0473*	0.899 (4)
H3c28	0.135948	1.068532	0.148357	0.0473*	0.899 (4)
H1c23	0.361769	0.393343	0.351577	0.0378*
H1c24	0.300297	0.441351	0.511081	0.0373*
H1c8	0.06796	0.908229	0.420618	0.0373*
H2c8	0.090006	0.762114	0.374792	0.0373*
H1c6	−0.061615	0.975461	0.35501	0.04*
H1c5	−0.157476	0.9996	0.215351	0.0429*
H1c27	0.113089	1.118473	0.322895	0.0336*	0.899 (4)
H1c26	0.256822	1.200587	0.355095	0.0346*	0.899 (4)
H2c26	0.208953	1.141634	0.455632	0.0346*	0.899 (4)
H1c15	0.516029	1.362475	0.572938	0.046*
C28'	0.2525 (10)	1.162 (2)	0.2369 (11)	0.042 (6)	0.101 (4)
H1o1	0.1465 (13)	0.812 (2)	0.2010 (16)	0.0402*
H1o19	0.3584 (15)	1.002 (2)	0.3010 (17)	0.0552*
H1c26'	0.125922	1.075665	0.419702	0.0336*	0.101 (4)
H2c26'	0.114337	1.105645	0.288888	0.0336*	0.101 (4)
H1c27'	0.237554	1.19909	0.390453	0.0346*	0.101 (4)
H1c28'	0.252753	1.082083	0.190266	0.0509*	0.101 (4)
H2c28'	0.214686	1.230137	0.208928	0.0509*	0.101 (4)
H3c28'	0.304301	1.204201	0.241575	0.0509*	0.101 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0253 (6)	0.0372 (7)	0.0383 (7)	0.0031 (5)	0.0046 (5)	−0.0046 (5)
O19	0.0470 (8)	0.0509 (9)	0.0409 (8)	−0.0076 (7)	0.0101 (7)	−0.0169 (6)
N11	0.0290 (7)	0.0204 (7)	0.0290 (7)	−0.0013 (6)	−0.0014 (6)	0.0009 (6)
N9	0.0251 (7)	0.0219 (7)	0.0314 (7)	−0.0004 (6)	0.0008 (6)	0.0031 (6)
C3	0.0309 (9)	0.0308 (9)	0.0353 (9)	−0.0024 (7)	0.0035 (7)	0.0023 (7)
C17	0.0241 (8)	0.0393 (11)	0.0373 (10)	0.0043 (8)	0.0043 (7)	0.0022 (8)
C22	0.0260 (8)	0.0305 (9)	0.0348 (9)	−0.0043 (7)	0.0045 (7)	−0.0092 (7)
C2	0.0250 (8)	0.0234 (8)	0.0366 (9)	−0.0016 (7)	0.0048 (7)	0.0012 (7)
C18	0.0269 (8)	0.0295 (9)	0.0336 (9)	0.0071 (7)	−0.0008 (7)	−0.0054 (7)
C21	0.0282 (8)	0.0271 (9)	0.0278 (8)	−0.0047 (7)	0.0003 (7)	−0.0002 (7)
C4	0.0286 (9)	0.0318 (10)	0.0455 (11)	−0.0007 (8)	−0.0045 (8)	0.0070 (8)
C16	0.0252 (9)	0.0362 (10)	0.0459 (11)	−0.0027 (8)	−0.0037 (8)	0.0094 (9)
C13	0.0283 (8)	0.0252 (9)	0.0287 (8)	0.0028 (7)	−0.0034 (7)	0.0024 (7)
C25	0.0243 (8)	0.0265 (9)	0.0315 (9)	−0.0021 (7)	0.0024 (7)	0.0013 (7)
C10	0.0285 (8)	0.0250 (9)	0.0248 (8)	−0.0010 (7)	0.0022 (7)	0.0013 (7)
C20	0.0222 (8)	0.0228 (8)	0.0271 (8)	−0.0028 (7)	−0.0003 (6)	−0.0018 (6)
C12	0.0377 (10)	0.0288 (9)	0.0263 (8)	−0.0036 (8)	−0.0031 (7)	0.0019 (7)
C14	0.0382 (10)	0.0365 (10)	0.0269 (9)	−0.0061 (8)	−0.0034 (7)	0.0017 (7)
C7	0.0244 (8)	0.0245 (9)	0.0339 (9)	−0.0008 (7)	0.0042 (7)	0.0018 (7)
C28	0.0519 (14)	0.0285 (11)	0.0372 (11)	−0.0055 (10)	−0.0041 (10)	0.0045 (9)
C23	0.0228 (8)	0.0243 (9)	0.0473 (10)	−0.0008 (7)	0.0011 (7)	−0.0053 (8)
C24	0.0272 (8)	0.0257 (9)	0.0402 (10)	−0.0012 (7)	0.0014 (7)	0.0053 (7)
C8	0.0265 (9)	0.0350 (10)	0.0322 (9)	−0.0002 (8)	0.0066 (7)	0.0009 (7)
C6	0.0278 (9)	0.0306 (10)	0.0420 (10)	0.0023 (7)	0.0069 (8)	−0.0016 (8)
C5	0.0256 (9)	0.0319 (10)	0.0499 (11)	0.0037 (8)	0.0041 (8)	0.0004 (8)
C27	0.0277 (11)	0.0219 (9)	0.0344 (13)	0.0017 (8)	0.0008 (9)	0.0021 (8)
C26	0.0352 (10)	0.0208 (9)	0.0304 (13)	0.0011 (8)	0.0013 (9)	−0.0022 (8)
C26'	0.0277 (11)	0.0219 (9)	0.0344 (13)	0.0017 (8)	0.0008 (9)	0.0021 (8)
C27'	0.0352 (10)	0.0208 (9)	0.0304 (13)	0.0011 (8)	0.0013 (9)	−0.0022 (8)
C15	0.0405 (10)	0.0361 (11)	0.0372 (10)	−0.0099 (9)	−0.0084 (8)	0.0007 (8)
C28'	0.036 (10)	0.052 (13)	0.039 (11)	−0.021 (9)	−0.002 (8)	0.016 (9)

Geometric parameters (Å, º) top

O1—C2	1.374 (2)	C10—H1c10	0.96
O19—C18	1.369 (2)	C12—H1c12	0.96
N11—C10	1.467 (2)	C12—H2c12	0.96
N11—C12	1.465 (2)	C14—C15	1.389 (3)
N11—C26	1.469 (2)	C14—H1c14	0.96
N11—C27'	1.500 (12)	C7—C8	1.501 (2)
N9—C10	1.469 (2)	C7—C6	1.394 (2)
N9—C8	1.473 (2)	C28—C27	1.521 (3)
N9—C27	1.500 (2)	C28—H1c28	0.96
N9—C26'	1.469 (6)	C28—H2c28	0.96
C3—C2	1.380 (2)	C28—H3c28	0.96
C3—C4	1.390 (3)	C23—C24	1.381 (3)
C3—H1c3	0.96	C23—H1c23	0.96
C17—C18	1.389 (2)	C24—H1c24	0.96
C17—C16	1.378 (3)	C8—H1c8	0.96
C17—H1c17	0.96	C8—H2c8	0.96
C22—C21	1.381 (2)	C6—C5	1.381 (3)
C22—C23	1.385 (3)	C6—H1c6	0.96
C22—H1c22	0.96	C5—H1c5	0.96
C2—C7	1.404 (2)	C27—C26	1.525 (3)
C18—C13	1.401 (2)	C27—H1c27	0.96
C21—C20	1.395 (2)	C26—H1c26	0.96
C21—H1c21	0.96	C26—H2c26	0.96
C4—C5	1.380 (3)	C26'—C27'	1.525 (19)
C4—H1c4	0.96	C26'—H1c26'	0.96
C16—C15	1.379 (3)	C26'—H2c26'	0.96
C16—H1c16	0.96	C27'—C28'	1.52 (2)
C13—C12	1.505 (2)	C27'—H1c27'	0.96
C13—C14	1.385 (2)	C15—H1c15	0.96
C25—C20	1.386 (2)	C28'—H1c28'	0.96
C25—C24	1.386 (2)	C28'—H2c28'	0.96
C25—H1c25	0.96	C28'—H3c28'	0.96
C10—C20	1.509 (2)

C10—N11—C12	113.34 (13)	C2—C7—C6	117.97 (15)
C10—N11—C26	102.83 (13)	C8—C7—C6	122.06 (16)
C10—N11—C27'	103.5 (5)	C27—C28—H1c28	109.47
C12—N11—C26	112.84 (13)	C27—C28—H2c28	109.47
C12—N11—C27'	127.6 (5)	C27—C28—H3c28	109.47
C10—N9—C8	111.98 (13)	H1c28—C28—H2c28	109.47
C10—N9—C27	107.30 (13)	H1c28—C28—H3c28	109.47
C10—N9—C26'	103.2 (6)	H2c28—C28—H3c28	109.47
C8—N9—C27	114.89 (14)	C22—C23—C24	119.49 (16)
C8—N9—C26'	97.1 (6)	C22—C23—H1c23	120.25
C2—C3—C4	119.68 (17)	C24—C23—H1c23	120.25
C2—C3—H1c3	120.16	C25—C24—C23	120.18 (16)
C4—C3—H1c3	120.16	C25—C24—H1c24	119.91
C18—C17—C16	120.22 (17)	C23—C24—H1c24	119.91
C18—C17—H1c17	119.89	N9—C8—C7	110.91 (14)
C16—C17—H1c17	119.89	N9—C8—H1c8	109.47
C21—C22—C23	120.50 (16)	N9—C8—H2c8	109.47
C21—C22—H1c22	119.75	C7—C8—H1c8	109.47
C23—C22—H1c22	119.75	C7—C8—H2c8	109.47
O1—C2—C3	119.08 (15)	H1c8—C8—H2c8	108
O1—C2—C7	120.03 (14)	C7—C6—C5	121.38 (17)
C3—C2—C7	120.89 (16)	C7—C6—H1c6	119.31
O19—C18—C17	118.21 (16)	C5—C6—H1c6	119.31
O19—C18—C13	121.29 (15)	C4—C5—C6	119.63 (17)
C17—C18—C13	120.49 (16)	C4—C5—H1c5	120.19
C22—C21—C20	120.31 (15)	C6—C5—H1c5	120.19
C22—C21—H1c21	119.85	N9—C27—C28	111.35 (15)
C20—C21—H1c21	119.85	N9—C27—C26	103.51 (14)
C3—C4—C5	120.43 (17)	N9—C27—H1c27	113.22
C3—C4—H1c4	119.78	C28—C27—C26	112.46 (17)
C5—C4—H1c4	119.78	C28—C27—H1c27	104.42
C17—C16—C15	120.21 (17)	C26—C27—H1c27	112.13
C17—C16—H1c16	119.9	N11—C26—C27	101.74 (14)
C15—C16—H1c16	119.9	N11—C26—H1c26	109.47
C18—C13—C12	120.74 (15)	N11—C26—H2c26	109.47
C18—C13—C14	117.97 (16)	C27—C26—H1c26	109.47
C12—C13—C14	121.27 (15)	C27—C26—H2c26	109.47
C20—C25—C24	120.70 (16)	H1c26—C26—H2c26	116.23
C20—C25—H1c25	119.65	N9—C26'—H1c26'	109.47
C24—C25—H1c25	119.65	N9—C26'—H2c26'	109.47
N11—C10—N9	102.44 (12)	C27'—C26'—H1c26'	109.47
N11—C10—C20	112.26 (13)	C27'—C26'—H2c26'	109.47
N11—C10—H1c10	113.69	H1c26'—C26'—H2c26'	120.28
N9—C10—C20	113.32 (13)	N11—C27'—C26'	107.3 (8)
N9—C10—H1c10	112.64	N11—C27'—C28'	113.3 (11)
C20—C10—H1c10	102.9	N11—C27'—H1c27'	109.44
C21—C20—C25	118.82 (15)	C26'—C27'—C28'	112.5 (12)
C21—C20—C10	120.40 (14)	C26'—C27'—H1c27'	110.35
C25—C20—C10	120.77 (14)	C28'—C27'—H1c27'	103.96
N11—C12—C13	112.27 (13)	C16—C15—C14	119.45 (17)
N11—C12—H1c12	109.47	C16—C15—H1c15	120.27
N11—C12—H2c12	109.47	C14—C15—H1c15	120.27
C13—C12—H1c12	109.47	C27'—C28'—H1c28'	109.47
C13—C12—H2c12	109.47	C27'—C28'—H2c28'	109.47
H1c12—C12—H2c12	106.52	C27'—C28'—H3c28'	109.47
C13—C14—C15	121.65 (17)	H1c28'—C28'—H2c28'	109.47
C13—C14—H1c14	119.18	H1c28'—C28'—H3c28'	109.47
C15—C14—H1c14	119.17	H2c28'—C28'—H3c28'	109.47
C2—C7—C8	119.96 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o1···N9	0.98 (2)	1.88 (2)	2.7569 (18)	147.7 (19)
O19—H1o19···N11	1.00 (2)	1.79 (2)	2.709 (2)	152 (2)
O1—H1o1···C8	0.98 (2)	2.32 (2)	2.844 (2)	112.5 (16)
O19—H1o19···C12	1.00 (2)	2.27 (2)	2.884 (2)	118.6 (16)
O19—H1o19···C28′	1.00 (2)	2.45 (3)	2.877 (18)	105.1 (16)
C26′—H2c26′···C28	0.96	1.63	2.082 (17)	103.83
C28′—H3c28′···O19	0.96	2.35	2.877 (18)	114.12
C26—H1c26···C28′	0.96	1.52	1.973 (15)	102.84

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆N₂O₂
M_r	374.5
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	16.8974 (8), 9.4893 (5), 12.5287 (6)
β (°)	92.928 (4)
V (Å³)	2006.29 (17)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.35 × 0.25 × 0.09

Data collection
Diffractometer	Agilent Xcalibur (Atlas, Gemini ultra) diffractometer
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.886, 0.952
No. of measured, independent and observed [I > 3σ(I)] reflections	8259, 3491, 2704
R_int	0.03
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.113, 1.51
No. of reflections	3491
No. of parameters	276
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.18

Computer programs: CrysAlis PRO (Agilent, 2010), SUPERFLIP (Palatinus & Chapuis 2007), JANA2006 (Petříček et al. 2006), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o1···N9	0.98 (2)	1.88 (2)	2.7569 (18)	147.7 (19)
O19—H1o19···N11	1.00 (2)	1.79 (2)	2.709 (2)	152 (2)

Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB), and the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences (ASCR).

References

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