4,4′-Di-tert-butyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol

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

doi:10.1107/S1600536813017157

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1166

https://doi.org/10.1107/S1600536813017157

Open

access

4,4′-Di-tert-butyl-2,2′-[imidazolidine-1,3-diylbis(methylene)]diphenol

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

^aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, 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 18 June 2013; accepted 20 June 2013; online 29 June 2013)

In the title compound, C₂₅H₃₆N₂O₂, the two tert-butyl-substituted benzene rings are inclined at an angle of 53.5 (3)° to one another. The imidazolidine ring has an envelope conformation with with one of the C atoms of the ethylene fragment as the flap. The structure displays two intramolecular O—H⋯N hydrogen bonds that generate S(6) ring motifs. The crystal studied was a non-merohedral twin with a fractional contribution of 0.281(6) for the minor domain.

Related literature

For related structures, see: Rivera et al. (2011 , 2012a ,b ); Rivera, Nerio, Ríos-Motta, Fejfarová et al. (2012 ). For the use of the 2,2′-[imidazolidine-1,3-diylbis(methylene)]diphenol system as a ligand in the synthesis of a variety of coordination compounds, see: Kober et al. (2012 ); Xu et al. (2007 ); Zhang et al. (2009 ). For the original synthesis of the title compound, see: Rivera et al. (1993 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₅H₃₆N₂O₂
M_r = 396.56
Monoclinic, P 2₁ /c
a = 21.0879 (16) Å
b = 6.2110 (4) Å
c = 17.9086 (16) Å
β = 109.168 (6)°
V = 2215.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.24 × 0.22 × 0.19 mm

Data collection

Stoe IPDS II two-circle diffractometer
22835 measured reflections
3909 independent reflections
3131 reflections with I > 2σ(I)
R_int = 0.101

Refinement

R[F² > 2σ(F²)] = 0.119
wR(F²) = 0.324
S = 1.13
3909 reflections
272 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.00 (10)	1.70 (10)	2.655 (7)	157 (8)
O2—H2⋯N2	0.95 (8)	1.83 (8)	2.656 (7)	144 (7)

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: XRED-32 (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813017157/sj5337sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017157/sj5337Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813017157/sj5337Isup3.cml

checkCIF report

Comment top

2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol system has been used as ligand in the synthesis of a variety of coordination compounds, with potential applications in homogeneous catalysis (Kober et al., 2012, Xu et al., 2007, Zhang et al., 2009). The molecular structure and atom-numbering scheme for (I) are shown in Fig. 1. The imidazolidine ring adopts an envelope conformation, with C3 as the flap. The dihedral angle between aromatic rings is 53.5 (3)°. Its X-ray structure confirms the presence of two intramolecular hydrogen bonds between the phenolic hydroxyl groups and the imidazolidine nitrogen atoms with S(6) graph-set motifs (Bernstein et al., 1995) (Table 1).

Related literature top

For related structures, see: Rivera et al. (2011, 2012a, 2012b); Rivera, Nerio, Ríos-Motta, Fejfarová et al. (2012). For the use of the 2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol system as a ligand in the synthesis of a variety of coordination compounds, see: Kober et al. (2012); Xu et al. (2007); Zhang et al. (2009). For the original synthesis of the title compound, see: Rivera et al. (1993). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

For the original synthesis of the title compound, see: Rivera et al. (1993). Single crystals suitable for X-ray diffraction were obtained from a mixture chloroform:methanol (1:1), by slow evaporation over 5 days at room temperature.

Structure description top

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: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, displacement ellipsoids are drawn at the 50% probability level. Intramolecular hydrogen bonds are drawn as dashed lines.

4,4'-Di-tert-butyl-2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol top

Crystal data top

C₂₅H₃₆N₂O₂	F(000) = 864
M_r = 396.56	D_x = 1.189 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.0879 (16) Å	Cell parameters from 20905 reflections
b = 6.2110 (4) Å	θ = 2.1–26.0°
c = 17.9086 (16) Å	µ = 0.08 mm⁻¹
β = 109.168 (6)°	T = 173 K
V = 2215.6 (3) Å³	Block, colourless
Z = 4	0.24 × 0.22 × 0.19 mm

Data collection top

Stoe IPDS II two-circle diffractometer	R_int = 0.101
Radiation source: Genix 3D IµS microfocus X-ray source	θ_max = 25.0°, θ_min = 2.1°
ω scans	h = −25→24
22835 measured reflections	k = −7→7
3909 independent reflections	l = −18→21
3131 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.119	w = 1/[σ²(F_o²) + (0.0705P)² + 10.9502P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.324	(Δ/σ)_max < 0.001
S = 1.13	Δρ_max = 0.42 e Å⁻³
3909 reflections	Δρ_min = −0.39 e Å⁻³
272 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.037 (4)

Crystal data top

C₂₅H₃₆N₂O₂	V = 2215.6 (3) Å³
M_r = 396.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.0879 (16) Å	µ = 0.08 mm⁻¹
b = 6.2110 (4) Å	T = 173 K
c = 17.9086 (16) Å	0.24 × 0.22 × 0.19 mm
β = 109.168 (6)°

Data collection top

Stoe IPDS II two-circle diffractometer	3131 reflections with I > 2σ(I)
22835 measured reflections	R_int = 0.101
3909 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.119	0 restraints
wR(F²) = 0.324	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0705P)² + 10.9502P] where P = (F_o² + 2F_c²)/3
3909 reflections	Δρ_max = 0.42 e Å⁻³
272 parameters	Δρ_min = −0.39 e Å⁻³

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. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
O1	0.4712 (2)	0.0117 (8)	0.5876 (3)	0.0455 (12)
H1	0.500 (5)	0.122 (16)	0.624 (6)	0.09 (3)*
O2	0.6663 (2)	0.9590 (8)	0.7246 (3)	0.0455 (12)
H2	0.635 (4)	0.845 (13)	0.716 (5)	0.06 (2)*
N1	0.5256 (3)	0.3720 (9)	0.6606 (3)	0.0385 (13)
N2	0.6261 (3)	0.5545 (8)	0.7268 (3)	0.0368 (13)
C1	0.5734 (3)	0.4179 (13)	0.7397 (4)	0.0489 (18)
H1A	0.5929	0.2827	0.7669	0.059*
H1B	0.5508	0.4945	0.7724	0.059*
C2	0.5537 (3)	0.4692 (12)	0.6021 (4)	0.0433 (16)
H2A	0.5346	0.6139	0.5854	0.052*
H2B	0.5453	0.3765	0.5549	0.052*
C3	0.6280 (3)	0.4820 (11)	0.6489 (4)	0.0369 (14)
H3A	0.6501	0.3398	0.6525	0.044*
H3B	0.6513	0.5875	0.6256	0.044*
C4	0.4565 (3)	0.4390 (11)	0.6528 (4)	0.0419 (16)
H4A	0.4524	0.5964	0.6437	0.050*
H4B	0.4483	0.4089	0.7031	0.050*
C5	0.6896 (3)	0.5301 (11)	0.7933 (4)	0.0394 (15)
H5A	0.7046	0.3785	0.7960	0.047*
H5B	0.6813	0.5639	0.8434	0.047*
C11	0.4026 (3)	0.3260 (10)	0.5857 (4)	0.0364 (14)
C12	0.4124 (3)	0.1211 (11)	0.5592 (4)	0.0407 (15)
C13	0.3586 (4)	0.0247 (11)	0.5019 (4)	0.0492 (18)
H13	0.3648	−0.1113	0.4810	0.059*
C14	0.2970 (4)	0.1210 (11)	0.4750 (4)	0.0449 (16)
H14	0.2617	0.0508	0.4354	0.054*
C15	0.2846 (3)	0.3197 (10)	0.5040 (4)	0.0399 (15)
C16	0.3396 (3)	0.4209 (11)	0.5576 (4)	0.0421 (16)
H16	0.3339	0.5608	0.5758	0.050*
C17	0.2157 (3)	0.4268 (12)	0.4738 (4)	0.0420 (16)
C18	0.2078 (4)	0.5451 (13)	0.3962 (4)	0.0518 (19)
H18A	0.2141	0.4431	0.3574	0.078*
H18B	0.2415	0.6596	0.4057	0.078*
H18C	0.1628	0.6081	0.3758	0.078*
C19	0.2058 (4)	0.5876 (14)	0.5326 (4)	0.055 (2)
H19A	0.2104	0.5144	0.5825	0.082*
H19B	0.1609	0.6510	0.5114	0.082*
H19C	0.2396	0.7015	0.5417	0.082*
C20	0.1589 (4)	0.2555 (15)	0.4574 (6)	0.066 (2)
H20A	0.1629	0.1777	0.5063	0.099*
H20B	0.1630	0.1537	0.4174	0.099*
H20C	0.1152	0.3272	0.4381	0.099*
C21	0.7443 (3)	0.6742 (10)	0.7855 (4)	0.0363 (14)
C22	0.7299 (3)	0.8793 (10)	0.7516 (4)	0.0403 (15)
C23	0.7822 (3)	1.0074 (11)	0.7463 (4)	0.0434 (16)
H23	0.7731	1.1453	0.7222	0.052*
C24	0.8475 (3)	0.9344 (11)	0.7760 (4)	0.0434 (16)
H24	0.8825	1.0241	0.7715	0.052*
C25	0.8639 (3)	0.7346 (11)	0.8122 (4)	0.0422 (16)
C26	0.8101 (3)	0.6077 (10)	0.8153 (4)	0.0366 (14)
H26	0.8194	0.4693	0.8390	0.044*
C27	0.9369 (3)	0.6602 (12)	0.8458 (5)	0.0506 (18)
C28	0.9627 (4)	0.613 (2)	0.7759 (6)	0.090 (4)
H28A	0.9588	0.7433	0.7438	0.135*
H28B	0.9359	0.4975	0.7432	0.135*
H28C	1.0099	0.5687	0.7964	0.135*
C29	0.9436 (4)	0.4555 (14)	0.8947 (6)	0.069 (2)
H29A	0.9159	0.3417	0.8619	0.103*
H29B	0.9286	0.4836	0.9401	0.103*
H29C	0.9907	0.4094	0.9134	0.103*
C30	0.9809 (4)	0.8335 (14)	0.8977 (6)	0.071 (3)
H30A	0.9768	0.9669	0.8672	0.106*
H30B	1.0278	0.7858	0.9156	0.106*
H30C	0.9665	0.8595	0.9436	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.044 (3)	0.040 (3)	0.055 (3)	0.004 (2)	0.020 (2)	−0.007 (2)
O2	0.039 (3)	0.036 (3)	0.055 (3)	0.004 (2)	0.007 (2)	0.006 (2)
N1	0.034 (3)	0.046 (3)	0.039 (3)	−0.001 (2)	0.017 (2)	0.001 (2)
N2	0.033 (3)	0.039 (3)	0.037 (3)	−0.003 (2)	0.011 (2)	−0.003 (2)
C1	0.039 (4)	0.055 (4)	0.053 (4)	−0.012 (3)	0.014 (3)	0.000 (4)
C2	0.039 (4)	0.047 (4)	0.041 (4)	0.003 (3)	0.010 (3)	0.001 (3)
C3	0.039 (3)	0.038 (3)	0.033 (3)	−0.004 (3)	0.011 (3)	−0.004 (3)
C4	0.036 (3)	0.042 (4)	0.051 (4)	−0.001 (3)	0.020 (3)	−0.008 (3)
C5	0.036 (3)	0.044 (4)	0.036 (3)	0.001 (3)	0.009 (3)	0.002 (3)
C11	0.037 (3)	0.032 (3)	0.041 (4)	−0.004 (3)	0.015 (3)	−0.003 (3)
C12	0.047 (4)	0.039 (4)	0.039 (3)	0.001 (3)	0.017 (3)	0.005 (3)
C13	0.060 (4)	0.032 (3)	0.052 (4)	−0.003 (3)	0.013 (4)	−0.005 (3)
C14	0.051 (4)	0.041 (4)	0.042 (4)	−0.008 (3)	0.014 (3)	−0.006 (3)
C15	0.040 (3)	0.038 (3)	0.042 (4)	−0.004 (3)	0.013 (3)	0.003 (3)
C16	0.038 (3)	0.036 (3)	0.050 (4)	−0.001 (3)	0.012 (3)	−0.001 (3)
C17	0.035 (3)	0.051 (4)	0.041 (4)	−0.001 (3)	0.014 (3)	0.006 (3)
C18	0.048 (4)	0.065 (5)	0.039 (4)	0.001 (4)	0.010 (3)	0.005 (3)
C19	0.048 (4)	0.068 (5)	0.046 (4)	0.013 (4)	0.012 (3)	0.000 (4)
C20	0.040 (4)	0.072 (5)	0.081 (6)	−0.012 (4)	0.011 (4)	0.006 (5)
C21	0.041 (3)	0.035 (3)	0.030 (3)	−0.004 (3)	0.009 (3)	−0.003 (3)
C22	0.042 (4)	0.035 (3)	0.044 (4)	0.000 (3)	0.013 (3)	−0.003 (3)
C23	0.055 (4)	0.036 (3)	0.037 (3)	−0.007 (3)	0.013 (3)	0.005 (3)
C24	0.042 (4)	0.047 (4)	0.043 (4)	−0.013 (3)	0.016 (3)	−0.003 (3)
C25	0.042 (4)	0.042 (4)	0.040 (4)	−0.005 (3)	0.010 (3)	−0.006 (3)
C26	0.036 (3)	0.036 (3)	0.035 (3)	0.001 (3)	0.008 (3)	−0.003 (3)
C27	0.040 (4)	0.055 (4)	0.052 (4)	−0.003 (3)	0.010 (3)	−0.007 (4)
C28	0.049 (5)	0.135 (10)	0.089 (7)	0.009 (6)	0.027 (5)	−0.027 (7)
C29	0.045 (4)	0.056 (5)	0.094 (7)	0.002 (4)	0.007 (4)	0.000 (5)
C30	0.055 (5)	0.055 (5)	0.085 (6)	−0.010 (4)	−0.001 (4)	−0.011 (5)

Geometric parameters (Å, º) top

O1—C12	1.357 (8)	C17—C18	1.533 (10)
O1—H1	1.00 (10)	C17—C20	1.556 (10)
O2—C22	1.360 (8)	C18—H18A	0.9800
O2—H2	0.95 (8)	C18—H18B	0.9800
N1—C1	1.473 (9)	C18—H18C	0.9800
N1—C4	1.478 (8)	C19—H19A	0.9800
N1—C2	1.490 (9)	C19—H19B	0.9800
N2—C1	1.476 (8)	C19—H19C	0.9800
N2—C5	1.479 (8)	C20—H20A	0.9800
N2—C3	1.479 (8)	C20—H20B	0.9800
C1—H1A	0.9900	C20—H20C	0.9800
C1—H1B	0.9900	C21—C26	1.377 (9)
C2—C3	1.517 (9)	C21—C22	1.401 (9)
C2—H2A	0.9900	C22—C23	1.389 (9)
C2—H2B	0.9900	C23—C24	1.378 (10)
C3—H3A	0.9900	C23—H23	0.9500
C3—H3B	0.9900	C24—C25	1.391 (10)
C4—C11	1.526 (9)	C24—H24	0.9500
C4—H4A	0.9900	C25—C26	1.397 (9)
C4—H4B	0.9900	C25—C27	1.529 (9)
C5—C21	1.503 (9)	C26—H26	0.9500
C5—H5A	0.9900	C27—C30	1.522 (10)
C5—H5B	0.9900	C27—C29	1.523 (12)
C11—C16	1.388 (9)	C27—C28	1.549 (12)
C11—C12	1.397 (9)	C28—H28A	0.9800
C12—C13	1.392 (10)	C28—H28B	0.9800
C13—C14	1.365 (10)	C28—H28C	0.9800
C13—H13	0.9500	C29—H29A	0.9800
C14—C15	1.397 (9)	C29—H29B	0.9800
C14—H14	0.9500	C29—H29C	0.9800
C15—C16	1.390 (9)	C30—H30A	0.9800
C15—C17	1.526 (9)	C30—H30B	0.9800
C16—H16	0.9500	C30—H30C	0.9800
C17—C19	1.514 (10)

C12—O1—H1	101 (5)	C18—C17—C20	108.0 (6)
C22—O2—H2	110 (5)	C17—C18—H18A	109.5
C1—N1—C4	112.3 (5)	C17—C18—H18B	109.5
C1—N1—C2	107.0 (5)	H18A—C18—H18B	109.5
C4—N1—C2	115.3 (5)	C17—C18—H18C	109.5
C1—N2—C5	110.1 (5)	H18A—C18—H18C	109.5
C1—N2—C3	103.2 (5)	H18B—C18—H18C	109.5
C5—N2—C3	115.6 (5)	C17—C19—H19A	109.5
N1—C1—N2	105.8 (5)	C17—C19—H19B	109.5
N1—C1—H1A	110.6	H19A—C19—H19B	109.5
N2—C1—H1A	110.6	C17—C19—H19C	109.5
N1—C1—H1B	110.6	H19A—C19—H19C	109.5
N2—C1—H1B	110.6	H19B—C19—H19C	109.5
H1A—C1—H1B	108.7	C17—C20—H20A	109.5
N1—C2—C3	102.2 (5)	C17—C20—H20B	109.5
N1—C2—H2A	111.3	H20A—C20—H20B	109.5
C3—C2—H2A	111.3	C17—C20—H20C	109.5
N1—C2—H2B	111.3	H20A—C20—H20C	109.5
C3—C2—H2B	111.3	H20B—C20—H20C	109.5
H2A—C2—H2B	109.2	C26—C21—C22	119.3 (6)
N2—C3—C2	101.1 (5)	C26—C21—C5	119.5 (6)
N2—C3—H3A	111.5	C22—C21—C5	121.2 (6)
C2—C3—H3A	111.5	O2—C22—C23	118.7 (6)
N2—C3—H3B	111.5	O2—C22—C21	122.2 (6)
C2—C3—H3B	111.5	C23—C22—C21	119.1 (6)
H3A—C3—H3B	109.4	C24—C23—C22	120.0 (6)
N1—C4—C11	113.6 (5)	C24—C23—H23	120.0
N1—C4—H4A	108.8	C22—C23—H23	120.0
C11—C4—H4A	108.8	C23—C24—C25	122.5 (6)
N1—C4—H4B	108.8	C23—C24—H24	118.8
C11—C4—H4B	108.8	C25—C24—H24	118.8
H4A—C4—H4B	107.7	C24—C25—C26	116.2 (6)
N2—C5—C21	112.5 (5)	C24—C25—C27	121.2 (6)
N2—C5—H5A	109.1	C26—C25—C27	122.6 (6)
C21—C5—H5A	109.1	C21—C26—C25	122.9 (6)
N2—C5—H5B	109.1	C21—C26—H26	118.6
C21—C5—H5B	109.1	C25—C26—H26	118.6
H5A—C5—H5B	107.8	C30—C27—C29	108.5 (7)
C16—C11—C12	119.6 (6)	C30—C27—C25	111.1 (6)
C16—C11—C4	117.8 (6)	C29—C27—C25	111.7 (6)
C12—C11—C4	122.1 (6)	C30—C27—C28	108.7 (7)
O1—C12—C13	119.0 (6)	C29—C27—C28	108.4 (8)
O1—C12—C11	123.2 (6)	C25—C27—C28	108.4 (6)
C13—C12—C11	117.8 (6)	C27—C28—H28A	109.5
C14—C13—C12	121.5 (7)	C27—C28—H28B	109.5
C14—C13—H13	119.2	H28A—C28—H28B	109.5
C12—C13—H13	119.2	C27—C28—H28C	109.5
C13—C14—C15	121.9 (7)	H28A—C28—H28C	109.5
C13—C14—H14	119.0	H28B—C28—H28C	109.5
C15—C14—H14	119.0	C27—C29—H29A	109.5
C16—C15—C14	116.1 (6)	C27—C29—H29B	109.5
C16—C15—C17	121.9 (6)	H29A—C29—H29B	109.5
C14—C15—C17	121.8 (6)	C27—C29—H29C	109.5
C11—C16—C15	122.8 (6)	H29A—C29—H29C	109.5
C11—C16—H16	118.6	H29B—C29—H29C	109.5
C15—C16—H16	118.6	C27—C30—H30A	109.5
C19—C17—C15	112.0 (6)	C27—C30—H30B	109.5
C19—C17—C18	108.4 (6)	H30A—C30—H30B	109.5
C15—C17—C18	109.7 (6)	C27—C30—H30C	109.5
C19—C17—C20	108.0 (6)	H30A—C30—H30C	109.5
C15—C17—C20	110.6 (6)	H30B—C30—H30C	109.5

C4—N1—C1—N2	−123.4 (6)	C16—C15—C17—C19	−26.9 (9)
C2—N1—C1—N2	4.0 (7)	C14—C15—C17—C19	157.8 (7)
C5—N2—C1—N1	−154.4 (5)	C16—C15—C17—C18	93.5 (8)
C3—N2—C1—N1	−30.5 (7)	C14—C15—C17—C18	−81.8 (8)
C1—N1—C2—C3	23.1 (7)	C16—C15—C17—C20	−147.5 (7)
C4—N1—C2—C3	148.8 (5)	C14—C15—C17—C20	37.2 (9)
C1—N2—C3—C2	44.4 (6)	N2—C5—C21—C26	−148.4 (6)
C5—N2—C3—C2	164.6 (5)	N2—C5—C21—C22	34.6 (8)
N1—C2—C3—N2	−41.3 (6)	C26—C21—C22—O2	−176.7 (6)
C1—N1—C4—C11	−159.1 (6)	C5—C21—C22—O2	0.3 (10)
C2—N1—C4—C11	77.9 (7)	C26—C21—C22—C23	2.4 (9)
C1—N2—C5—C21	−177.0 (6)	C5—C21—C22—C23	179.4 (6)
C3—N2—C5—C21	66.5 (7)	O2—C22—C23—C24	177.5 (6)
N1—C4—C11—C16	−160.5 (6)	C21—C22—C23—C24	−1.6 (10)
N1—C4—C11—C12	27.4 (9)	C22—C23—C24—C25	−0.4 (11)
C16—C11—C12—O1	−175.5 (6)	C23—C24—C25—C26	1.6 (10)
C4—C11—C12—O1	−3.6 (10)	C23—C24—C25—C27	−178.9 (7)
C16—C11—C12—C13	3.2 (10)	C22—C21—C26—C25	−1.2 (10)
C4—C11—C12—C13	175.2 (6)	C5—C21—C26—C25	−178.2 (6)
O1—C12—C13—C14	175.6 (7)	C24—C25—C26—C21	−0.8 (10)
C11—C12—C13—C14	−3.2 (11)	C27—C25—C26—C21	179.7 (6)
C12—C13—C14—C15	−0.7 (11)	C24—C25—C27—C30	48.9 (10)
C13—C14—C15—C16	4.5 (10)	C26—C25—C27—C30	−131.5 (8)
C13—C14—C15—C17	−180.0 (7)	C24—C25—C27—C29	170.2 (7)
C12—C11—C16—C15	0.7 (10)	C26—C25—C27—C29	−10.3 (10)
C4—C11—C16—C15	−171.6 (6)	C24—C25—C27—C28	−70.4 (9)
C14—C15—C16—C11	−4.4 (10)	C26—C25—C27—C28	109.1 (9)
C17—C15—C16—C11	180.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.00 (10)	1.70 (10)	2.655 (7)	157 (8)
O2—H2···N2	0.95 (8)	1.83 (8)	2.656 (7)	144 (7)

Experimental details

Crystal data
Chemical formula	C₂₅H₃₆N₂O₂
M_r	396.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	21.0879 (16), 6.2110 (4), 17.9086 (16)
β (°)	109.168 (6)
V (Å³)	2215.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.22 × 0.19

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22835, 3909, 3131
R_int	0.101
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.119, 0.324, 1.13
No. of reflections	3909
No. of parameters	272
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0705P)² + 10.9502P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.39

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.00 (10)	1.70 (10)	2.655 (7)	157 (8)
O2—H2···N2	0.95 (8)	1.83 (8)	2.656 (7)	144 (7)

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.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Kober, E., Nerkowski, T., Janas, Z. & Jerzykiewicz, L. B. (2012). Dalton Trans. 41, 5188–5192. Web of Science CSD CrossRef CAS PubMed Google Scholar
Rivera, A., Gallo, G. I., Gayón, M. E. & Joseph-Nathan, P. (1993). Synth. Commun. 23, 2921–2929. CrossRef CAS Web of Science Google Scholar
Rivera, A., Nerio, L. S., Ríos-Motta, J., Fejfarová, K. & Dušek, M. (2012). Acta Cryst. E68, o170–o171. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rivera, A., Nerio, L. S., Ríos-Motta, J., Kučeráková, M. & Dušek, M. (2012a). Acta Cryst. E68, o3043–o3044. CSD CrossRef CAS IUCr Journals Google Scholar
Rivera, A., Nerio, L. S., Ríos-Motta, J., Kučeraková, M. & Dušek, M. (2012b). Acta Cryst. E68, o3172. CSD CrossRef IUCr Journals Google Scholar
Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Pojarová, M. & Dušek, M. (2011). Acta Cryst. E67, o2581. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA and XRED-32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Xu, X., Yao, Y., Zhang, Y. & Shen, Q. (2007). Inorg. Chem. 46, 3743–3751. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhang, Z., Xu, X., Li, W., Yao, Y., Zhang, Y., Shen, Q. & Luo, Y. (2009). Inorg. Chem. 48, 5715–5724. Web of Science CSD CrossRef PubMed CAS Google Scholar