4,4′-Dimethyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol

Rivera, A.; Nerio, L.S.; Ríos-Motta, J.; Kučeraková, M.; Dušek, M.

doi:10.1107/S1600536812042808

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3172

doi:10.1107/S1600536812042808

Open

access

4,4′-Dimethyl-2,2′-[imidazolidine-1,3-diylbis(methylene)]diphenol

Augusto Rivera,^a ^* Luz Stella Nerio,^a Jaime Ríos-Motta,^a Monika Kučeraková ^b and Michal Dušek ^b

^aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No.45-03, Bogotá, Código Postal 111321, Colombia, and ^bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: ariverau@unal.edu.co

(Received 15 September 2012; accepted 12 October 2012; online 20 October 2012)

The imidazolidine ring in the title compound, C₁₉H₂₄N₂O₂, adopts a twist conformation and its mean plane (r.m.s. deviation = 0.19 Å) makes dihedral angles of 72.38 (9) and 71.64 (9)° with the two pendant aromatic rings. The dihedral angle between the phenyl rings is 55.94 (8)°. The molecular structure shows the presence of two intramolecular O—H⋯N hydrogen bonds between the phenolic hydroxyl groups and N atoms with graph-set motif S(6). In the crystal, C—H⋯O hydrogen bonds lead to the formation of chains along the b-axis direction.

Related literature

For the anti-inflammatory and analgesic properties of imidazolidines, see: Sharma & Khan (2001 ). For related structures, see: Rivera et al. (2011 , 2012 ). For the preparation of the title compound, see: Rivera et al. (1993 ). For standard bond lengths, see: Allen et al. (1987 ). For ring conformations, see Cremer & Pople (1975 ). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₂₄N₂O₂
M_r = 312.4
Monoclinic, P 2₁ /n
a = 11.5029 (4) Å
b = 9.5001 (3) Å
c = 16.1874 (6) Å
β = 107.078 (3)°
V = 1690.94 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 120 K
0.25 × 0.22 × 0.13 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.573, T_max = 1
12982 measured reflections
3007 independent reflections
2648 reflections with I > 3σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.104
S = 1.93
3007 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H2⋯N2	0.912 (17)	1.869 (16)	2.6893 (13)	148.6 (16)
O2—H1⋯N1	0.923 (17)	1.825 (15)	2.6807 (12)	153.0 (15)
C17—H1c17⋯O1ⁱ	0.96	2.48	3.4286 (14)	168.38
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

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/S1600536812042808/lr2083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042808/lr2083Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042808/lr2083Isup3.cml

checkCIF report

Comment top

The 1,3-imidazolidine system is intriguing because it is present in biologically active molecules with anti-inflammatory and analgesic properties (Sharma et al., 2001). In our current investigations of factors which influence intramolecular hydrogen bond strength in 1,3-imidazolidine-bridged bis(phenols) (Rivera et al., 2011, 2012), we turn our attention to title compound (I) because the methyl substituent at the para-position in aromatic rings is an electron-donating group which makes the negative charge of hydroxyl group.

The molecular structure and atom-numbering scheme for (I) are shown in Fig. 1 The imidazolidine ring adopts a twist conformation, with twist about the C9—N2 bond; the puckering parameters (Cremer & Pople, 1975), Q2 = 0.4008 (13) Å and ϕ2 = 51.81 (18)°. Intraanular bond lengths (Allen et al., 1987) and angles of (I) are within normal ranges and are comparable to similar structures (Rivera et al., 2011, 2012). The mean plane of imidazolidine ring defined by N1, C15 and C14 makes a dihedral angle of 72.375 (85)° and 71.644 (96)° with the two pendant aromatic rings, C1/C2/C5/C10/C6/C17 and C3/C4/C7/C13/C16/C12 respectively. The dihedral angle between the phenyl rings is 55.938 (83)°. Its X-ray structure confirms the presence of intramolecular hydrogen bonds between the phenolic hydroxyl groups and nitrogen atoms with graph-set motif S(6) (Bernstein et al., 1995) (Table 1). The observed N···O distances [2.6807 (12) Å and 2.6893 (13) Å] and the observed C–O bond lengths [1.3701 (16) Å and 1.3715 (15) Å] are longer in relation to the unsubstituted related structures [2.6557 (13) Å and 1.3654 (15) Å, respectively] (Rivera et al., 2012) and p-chloro derivative [2.6524 (17) Å and 1.366 (2) Å, respectively] (Rivera et al., 2011). This result could indicate that the electro-donating nature of the methyl group at para-position influences the strength of the intra-molecular hydrogen bond.

In the crystal, intermolecular C—H···O hydrogen bonds lead to the formation of chains along the b axis, (Table 1, Fig. 2).

Related literature top

For the anti-inflammatory and analgesic properties of imidazolidines, see: Sharma & Khan (2001). For related structures, see: Rivera et al. (2011, 2012). For the preparation of the title compound, see: Rivera et al. (1993). For standard bond lengths, see: Allen et al. (1987). For ring conformations, see Cremer & Pople (1975). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995).

Experimental top

For the originally reported synthesis, see: Rivera et al. (1993)

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.
	Fig. 2. Packing of the molecules of the title compound view along b axis.

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

Crystal data top

C₁₉H₂₄N₂O₂	F(000) = 672
M_r = 312.4	D_x = 1.227 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 8356 reflections
a = 11.5029 (4) Å	θ = 4.0–66.9°
b = 9.5001 (3) Å	µ = 0.63 mm⁻¹
c = 16.1874 (6) Å	T = 120 K
β = 107.078 (3)°	Pyramidal shape, white
V = 1690.94 (10) Å³	0.25 × 0.22 × 0.13 mm
Z = 4

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	3007 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray source	2648 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.1°, θ_min = 4.2°
ω scans	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
T_min = 0.573, T_max = 1	l = −19→18
12982 measured reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.033	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0016I²)
wR(F²) = 0.104	(Δ/σ)_max = 0.0004
S = 1.93	Δρ_max = 0.16 e Å⁻³
3007 reflections	Δρ_min = −0.14 e Å⁻³
215 parameters	Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 1300 (400)
90 constraints

Crystal data top

C₁₉H₂₄N₂O₂	V = 1690.94 (10) Å³
M_r = 312.4	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 11.5029 (4) Å	µ = 0.63 mm⁻¹
b = 9.5001 (3) Å	T = 120 K
c = 16.1874 (6) Å	0.25 × 0.22 × 0.13 mm
β = 107.078 (3)°

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	3007 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2648 reflections with I > 3σ(I)
T_min = 0.573, T_max = 1	R_int = 0.021
12982 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.93	Δρ_max = 0.16 e Å⁻³
3007 reflections	Δρ_min = −0.14 e Å⁻³
215 parameters

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

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

	x	y	z	U_iso*/U_eq
O1	0.88856 (7)	0.44965 (9)	0.06241 (5)	0.0310 (3)
O2	0.64693 (7)	0.76997 (9)	−0.30769 (6)	0.0290 (3)
N1	0.76722 (9)	0.73615 (10)	−0.13993 (6)	0.0266 (3)
N2	0.84361 (8)	0.71755 (10)	0.00889 (6)	0.0261 (3)
C1	0.74585 (10)	0.70626 (11)	−0.32261 (7)	0.0251 (3)
C2	0.82536 (10)	0.62323 (11)	−0.25869 (7)	0.0243 (3)
C3	0.76676 (10)	0.60644 (12)	0.12013 (7)	0.0247 (3)
C4	0.80273 (10)	0.47037 (12)	0.10465 (7)	0.0267 (4)
C5	0.92398 (10)	0.56062 (11)	−0.27747 (7)	0.0245 (3)
C6	0.86516 (11)	0.66039 (12)	−0.41913 (7)	0.0290 (4)
C7	0.75212 (11)	0.35433 (13)	0.13319 (8)	0.0313 (4)
C8	1.05237 (11)	0.50485 (13)	−0.37565 (8)	0.0305 (4)
C9	0.72950 (10)	0.71770 (12)	−0.06231 (7)	0.0273 (4)
C10	0.94551 (10)	0.57626 (12)	−0.35724 (7)	0.0261 (4)
C11	0.80246 (10)	0.60126 (12)	−0.17246 (7)	0.0256 (4)
C12	0.67858 (10)	0.62103 (12)	0.16280 (7)	0.0262 (4)
C13	0.66608 (11)	0.37235 (13)	0.17686 (8)	0.0315 (4)
C14	0.91127 (11)	0.83498 (14)	−0.01388 (8)	0.0336 (4)
C15	0.87305 (12)	0.83398 (13)	−0.11242 (8)	0.0335 (4)
C16	0.62725 (10)	0.50583 (12)	0.19224 (7)	0.0280 (4)
C17	0.76650 (11)	0.72510 (12)	−0.40199 (8)	0.0283 (4)
C18	0.82742 (10)	0.73307 (12)	0.09490 (7)	0.0272 (4)
C19	0.53567 (12)	0.52729 (15)	0.24135 (9)	0.0374 (4)
H1c5	0.979186	0.504614	−0.233853	0.0294*
H1c6	0.878406	0.67367	−0.474459	0.0348*
H1c7	0.776818	0.261183	0.122626	0.0375*
H1c8	1.072127	0.552979	−0.421921	0.0366*
H2c8	1.121122	0.507333	−0.324784	0.0366*
H3c8	1.031868	0.408791	−0.391977	0.0366*
H1c9	0.689835	0.628276	−0.064525	0.0327*
H2c9	0.680476	0.796361	−0.055893	0.0327*
H1c11	0.738473	0.533616	−0.178617	0.0307*
H2c11	0.874835	0.565476	−0.131679	0.0307*
H1c12	0.652179	0.713903	0.172286	0.0315*
H1c13	0.632626	0.291154	0.196901	0.0378*
H1c14	0.996946	0.816774	0.007957	0.0403*
H2c14	0.886032	0.921709	0.006006	0.0403*
H1c15	0.848056	0.926862	−0.133682	0.0402*
H2c15	0.938576	0.798444	−0.131927	0.0402*
H1c17	0.712548	0.782964	−0.445198	0.034*
H1c18	0.77967	0.81553	0.09603	0.0327*
H2c18	0.905134	0.747643	0.136757	0.0327*
H1c19	0.480459	0.601158	0.21462	0.0449*
H2c19	0.491052	0.441692	0.240675	0.0449*
H3c19	0.577222	0.552689	0.300002	0.0449*
H1	0.6668 (13)	0.7721 (15)	−0.2481 (11)	0.0348*
H2	0.8974 (14)	0.5333 (17)	0.0373 (10)	0.0372*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0325 (5)	0.0315 (5)	0.0289 (4)	0.0074 (3)	0.0088 (3)	−0.0025 (3)
O2	0.0265 (4)	0.0304 (5)	0.0291 (5)	0.0048 (3)	0.0066 (3)	0.0029 (3)
N1	0.0280 (5)	0.0255 (5)	0.0267 (5)	0.0009 (4)	0.0087 (4)	0.0016 (4)
N2	0.0238 (5)	0.0292 (5)	0.0253 (5)	−0.0011 (4)	0.0073 (4)	−0.0005 (4)
C1	0.0243 (6)	0.0208 (5)	0.0284 (6)	−0.0011 (4)	0.0050 (4)	−0.0012 (4)
C2	0.0246 (5)	0.0209 (5)	0.0257 (6)	−0.0031 (4)	0.0048 (4)	0.0003 (4)
C3	0.0251 (5)	0.0261 (6)	0.0203 (5)	0.0005 (4)	0.0026 (4)	−0.0016 (4)
C4	0.0262 (6)	0.0287 (6)	0.0216 (5)	0.0036 (4)	0.0016 (4)	−0.0029 (4)
C5	0.0243 (5)	0.0202 (5)	0.0265 (6)	−0.0012 (4)	0.0034 (4)	0.0007 (4)
C6	0.0345 (6)	0.0273 (6)	0.0248 (6)	−0.0022 (5)	0.0081 (5)	−0.0005 (4)
C7	0.0379 (7)	0.0239 (6)	0.0273 (6)	0.0035 (5)	0.0023 (5)	−0.0017 (5)
C8	0.0311 (6)	0.0295 (6)	0.0311 (6)	−0.0002 (5)	0.0096 (5)	−0.0028 (5)
C9	0.0244 (6)	0.0298 (6)	0.0276 (6)	0.0021 (4)	0.0075 (5)	0.0014 (4)
C10	0.0268 (6)	0.0224 (5)	0.0281 (6)	−0.0032 (4)	0.0065 (4)	−0.0020 (4)
C11	0.0246 (5)	0.0239 (5)	0.0277 (6)	0.0007 (4)	0.0070 (4)	0.0029 (4)
C12	0.0265 (6)	0.0245 (6)	0.0260 (5)	0.0025 (4)	0.0050 (4)	−0.0004 (4)
C13	0.0356 (6)	0.0263 (6)	0.0291 (6)	−0.0046 (5)	0.0041 (5)	0.0024 (5)
C14	0.0305 (6)	0.0366 (7)	0.0344 (6)	−0.0081 (5)	0.0106 (5)	−0.0007 (5)
C15	0.0405 (7)	0.0263 (6)	0.0341 (7)	−0.0053 (5)	0.0114 (5)	0.0014 (5)
C16	0.0254 (6)	0.0292 (6)	0.0260 (6)	−0.0012 (4)	0.0025 (5)	0.0023 (5)
C17	0.0315 (6)	0.0243 (6)	0.0261 (6)	0.0006 (4)	0.0036 (5)	0.0032 (4)
C18	0.0286 (6)	0.0266 (6)	0.0268 (6)	−0.0008 (4)	0.0086 (5)	−0.0036 (4)
C19	0.0332 (7)	0.0377 (7)	0.0435 (7)	0.0000 (5)	0.0147 (6)	0.0070 (5)

Geometric parameters (Å, º) top

O1—C4	1.3701 (16)	C8—C10	1.5084 (18)
O1—H2	0.912 (17)	C8—H1c8	0.96
O2—C1	1.3715 (15)	C8—H2c8	0.96
O2—H1	0.923 (17)	C8—H3c8	0.96
N1—C9	1.4552 (17)	C9—H1c9	0.96
N1—C11	1.4863 (15)	C9—H2c9	0.96
N1—C15	1.4919 (15)	C11—H1c11	0.96
N2—C9	1.4707 (13)	C11—H2c11	0.96
N2—C14	1.4678 (17)	C12—C16	1.3924 (17)
N2—C18	1.4652 (17)	C12—H1c12	0.96
C1—C2	1.4048 (14)	C13—C16	1.3909 (17)
C1—C17	1.3852 (18)	C13—H1c13	0.96
C2—C5	1.3913 (17)	C14—C15	1.5250 (17)
C2—C11	1.5091 (18)	C14—H1c14	0.96
C3—C4	1.4022 (16)	C14—H2c14	0.96
C3—C12	1.3917 (18)	C15—H1c15	0.96
C3—C18	1.5061 (17)	C15—H2c15	0.96
C4—C7	1.3876 (18)	C16—C19	1.508 (2)
C5—C10	1.3923 (18)	C17—H1c17	0.96
C5—H1c5	0.96	C18—H1c18	0.96
C6—C10	1.3974 (15)	C18—H2c18	0.96
C6—C17	1.3884 (18)	C19—H1c19	0.96
C6—H1c6	0.96	C19—H2c19	0.96
C7—C13	1.385 (2)	C19—H3c19	0.96
C7—H1c7	0.96

C4—O1—H2	106.8 (11)	C6—C10—C8	121.43 (11)
C1—O2—H1	103.3 (10)	N1—C11—C2	110.39 (9)
C9—N1—C11	112.56 (9)	N1—C11—H1c11	109.47
C9—N1—C15	103.97 (9)	N1—C11—H2c11	109.47
C11—N1—C15	111.06 (9)	C2—C11—H1c11	109.47
C9—N2—C14	102.68 (9)	C2—C11—H2c11	109.47
C9—N2—C18	114.29 (9)	H1c11—C11—H2c11	108.54
C14—N2—C18	112.76 (9)	C3—C12—C16	122.39 (11)
O2—C1—C2	120.83 (11)	C3—C12—H1c12	118.8
O2—C1—C17	118.92 (9)	C16—C12—H1c12	118.81
C2—C1—C17	120.26 (11)	C7—C13—C16	121.26 (12)
C1—C2—C5	118.38 (11)	C7—C13—H1c13	119.37
C1—C2—C11	120.41 (11)	C16—C13—H1c13	119.37
C5—C2—C11	121.20 (9)	N2—C14—C15	104.28 (9)
C4—C3—C12	118.48 (11)	N2—C14—H1c14	109.47
C4—C3—C18	120.22 (11)	N2—C14—H2c14	109.47
C12—C3—C18	121.22 (10)	C15—C14—H1c14	109.47
O1—C4—C3	121.02 (11)	C15—C14—H2c14	109.47
O1—C4—C7	119.10 (11)	H1c14—C14—H2c14	114.2
C3—C4—C7	119.88 (12)	N1—C15—C14	105.98 (11)
C2—C5—C10	122.38 (9)	N1—C15—H1c15	109.47
C2—C5—H1c5	118.81	N1—C15—H2c15	109.47
C10—C5—H1c5	118.81	C14—C15—H1c15	109.47
C10—C6—C17	121.16 (12)	C14—C15—H2c15	109.47
C10—C6—H1c6	119.42	H1c15—C15—H2c15	112.75
C17—C6—H1c6	119.42	C12—C16—C13	117.69 (12)
C4—C7—C13	120.28 (11)	C12—C16—C19	120.40 (11)
C4—C7—H1c7	119.86	C13—C16—C19	121.88 (12)
C13—C7—H1c7	119.86	C1—C17—C6	120.07 (10)
C10—C8—H1c8	109.47	C1—C17—H1c17	119.97
C10—C8—H2c8	109.47	C6—C17—H1c17	119.97
C10—C8—H3c8	109.47	N2—C18—C3	112.06 (9)
H1c8—C8—H2c8	109.47	N2—C18—H1c18	109.47
H1c8—C8—H3c8	109.47	N2—C18—H2c18	109.47
H2c8—C8—H3c8	109.47	C3—C18—H1c18	109.47
N1—C9—N2	104.65 (9)	C3—C18—H2c18	109.47
N1—C9—H1c9	109.47	H1c18—C18—H2c18	106.76
N1—C9—H2c9	109.47	C16—C19—H1c19	109.47
N2—C9—H1c9	109.47	C16—C19—H2c19	109.47
N2—C9—H2c9	109.47	C16—C19—H3c19	109.47
H1c9—C9—H2c9	113.89	H1c19—C19—H2c19	109.47
C5—C10—C6	117.74 (11)	H1c19—C19—H3c19	109.47
C5—C10—C8	120.83 (9)	H2c19—C19—H3c19	109.47

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2···N2	0.912 (17)	1.869 (16)	2.6893 (13)	148.6 (16)
O2—H1···N1	0.923 (17)	1.825 (15)	2.6807 (12)	153.0 (15)
C17—H1c17···O1ⁱ	0.96	2.48	3.4286 (14)	168.38

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄N₂O₂
M_r	312.4
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	11.5029 (4), 9.5001 (3), 16.1874 (6)
β (°)	107.078 (3)
V (Å³)	1690.94 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.25 × 0.22 × 0.13

Data collection
Diffractometer	Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.573, 1
No. of measured, independent and observed [I > 3σ(I)] reflections	12982, 3007, 2648
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.104, 1.93
No. of reflections	3007
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

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—H2···N2	0.912 (17)	1.869 (16)	2.6893 (13)	148.6 (16)
O2—H1···N1	0.923 (17)	1.825 (15)	2.6807 (12)	153.0 (15)
C17—H1c17···O1ⁱ	0.96	2.48	3.4286 (14)	168.38

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

Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work as well as the Praemium Academiae project of the Academy of Sciences of the Czech Republic. LSN thanks COLCIENCIAS for a fellowship.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Petříček, V., Dusěk, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic. 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., Sadat-Bernal, J., Ríos-Motta, J., Pojarová, M. & Dušek, M. (2011). Acta Cryst. E67, o2581. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sharma, V. & Khan, M. S. Y. (2001). Eur. J. Med. Chem. 36, 651–658. Web of Science CrossRef PubMed CAS Google Scholar