Di-n-butyl 4,4′-dihy­droxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}dibenzoate

Rivera, A.; Quiroga, D.; Ríos-Motta, J.; Fejfarová, K.; Dušek, M.

doi:10.1107/S1600536811031205

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2297

doi:10.1107/S1600536811031205

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Di-n-butyl 4,4′-dihydroxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylene)}dibenzoate

Augusto Rivera,^a ^* Diego Quiroga,^a Jaime Ríos-Motta,^a Karla Fejfarová ^b and Michal Dušek ^b

^aDepartamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Bogotá, 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 29 July 2011; accepted 2 August 2011; online 11 August 2011)

The complete molecule of the title compound, C₃₁H₄₂N₂O₆, is generated by crystallographic twofold symmetry, with one C atom lying on the axis. The dihedral angle between the aromatic rings is 57.03 (6)°. The central heterocyclic ring adopts a half-chair conformation. The molecular conformation is stabilized by two intramolecular O—H⋯N hydrogen bonds with the N atoms of the heterocyclic ring as the acceptors. In the crystal, molecules are linked into chains along the c axis by non-classical C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Rivera et al. (2010 , 2011 ); Giordano et al. (1999 ); Feng & Grant (2006 ). For background to this work see: Koll et al. (2001 ); Filarowski et al. (2004 ).

Experimental

Crystal data

C₃₁H₄₂N₂O₆
M_r = 538.7
Monoclinic, C 2/c
a = 15.4471 (3) Å
b = 8.8103 (2) Å
c = 20.9374 (4) Å
β = 95.077 (2)°
V = 2838.27 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 120 K
0.38 × 0.28 × 0.20 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.868, T_max = 1.00
13938 measured reflections
2533 independent reflections
2157 reflections with I > 3σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.104
S = 1.73
2533 reflections
181 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5a⋯O1ⁱ	0.96	2.39	3.2393 (16)	148
O3—H3⋯N1	0.884 (18)	1.873 (18)	2.6859 (12)	152.0 (17)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); 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/S1600536811031205/bt5598sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031205/bt5598Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031205/bt5598Isup3.cml

checkCIF report

Comment top

Intramolecular hydrogen bonding interactions in Mannich bases lead to distortions in the aromatic rings due the existence of ortho-quinonoid resonance structures (Koll et al. 2001; Filarowski et al. 2004), which are evidenced in the bond and bond angle values. During our studies we have synthesized a series of symmetrical di-Mannich bases, by reaction between (2R,7R,11S,16S)-1,8,10,17-tetraazapentacyclo [8.8.1.1^8,17.0^2,7.0^11,16]icosane and p-halophenols. The intramolecular hydrogen bond interaction is weaker in the Mannich base having p-fluorine substituent [N···O 2.711 (2) Å] (Rivera et al. 2011) whereas in the case of the Mannich base p-chlorine substituted [N··· O 2.652 (2) Å] (Rivera et al. 2010), due to electron-withdrawing effect of chlorine atom. However, the distortion in the aromatic ring in these Mannich bases, leads to a conclusion indicating that the effect of halogen atoms seems to be no meaningful which can be explained on the basis of the presence of conjugative electron-release from lone pairs of halogen atom. To avoid the conjugation effect of halogen to aromatic ring we synthesized the title compound (I) which is a racemic Mannich base with a non-halogen electron withdrawing group in para position. The molecular structure and atom-numbering scheme for (I) are shown in Fig. 1. The X-ray diffraction analysis shows the existence of two intramolecular hydrogen bonding interactions between the hydroxy H atom and the amine groups in the heterocyclic ring (table 1).

The observed C11—O3 bond length [1.358 (2)Å] is in good agreement with the p-chlorophenol derivative (Rivera, et al. 2010) but is shorter by 0.01 Å in comparison with p-fluorophenol derivative (Rivera, et al. 2011). Though, in the title compound the X-ray analysis revealed the existence of distortions of the phenol ring in comparison with the related structures (Rivera et al. 2010, 2011), which was evident from the elongation of the C8—C9 bond length in title compound from [1.381 (2) Å, Rivera et al. 2011] to 1.393 (2) Å.

In comparison with the crystal packing of butylparaben, there are not head-to-tail hydrogen bonding interactions inside the chains that involve the O—H group as donor and the carbonyl O atom as acceptor (Giordano et al. 1999; Feng & Grant, 2006), there are non-classical hydrogen bonds C5—H5a··· O1 (table 1) which link neighboring helps stabilize the packing along c axis (Fig. 2).

Related literature top

For related structures, see: Rivera et al. (2010, 2011); Giordano et al. (1999); Feng & Grant (2006). For background to this work see: Koll et al. (2001); Filarowski et al. (2004).

Experimental top

A solution of (2R,7R,11S,16S)-1,8,10,17-tetraazapentacyclo [8.8.1.1^8,\17.0^2,7.0^11,16] icosane (276 mg, 1.00 mmol) in dioxane (3 ml) and water (4 ml), previously prepared following described procedures, was added dropwise in a dioxane solution (3 ml) containing two equivalents of n-butyl 4-hydroxybenzoate (388 mg, 2.00 mmol) in a two-necked round-bottomed flask. The mixture was refluxed for about 12 h and then the solvent was evaporated under reduced pressure until a sticky residue appeared. The product was purified by chromatography on a silica column, and subjected to gradient elution with benzene:ethyl acetate (yield 19%, m.p. = 414–416 K). Single crystals of racemic (I) were grown from a chloroform solution by slow evaporation of the solvent at room temperature over a period of about 2 weeks.

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: SIR2002 (Burla et al., 2003); 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 view of (I) with the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing of the molecules of the title compound view along b axis.

Di-n-butyl 4,4'-dihydroxy-3,3'-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octahydro- 1H-1,3-benzimidazole-1,3-diyl]bis(methylene)}dibenzoate top

Crystal data top

C₃₁H₄₂N₂O₆	F(000) = 1160
M_r = 538.7	D_x = 1.260 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 7161 reflections
a = 15.4471 (3) Å	θ = 2.9–67.0°
b = 8.8103 (2) Å	µ = 0.70 mm⁻¹
c = 20.9374 (4) Å	T = 120 K
β = 95.077 (2)°	Prism, colourless
V = 2838.27 (10) Å³	0.38 × 0.28 × 0.20 mm
Z = 4

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	2533 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2157 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.2°, θ_min = 4.2°
Rotation method data acquisition using ω scans	h = −17→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→10
T_min = 0.868, T_max = 1	l = −24→24
13938 measured reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.036	Weighting scheme based on measured s.u.'s w = 1/[σ²(I) + 0.0016I²]
wR(F²) = 0.104	(Δ/σ)_max = 0.009
S = 1.73	Δρ_max = 0.20 e Å⁻³
2533 reflections	Δρ_min = −0.19 e Å⁻³
181 parameters	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 2400 (500)
81 constraints

Crystal data top

C₃₁H₄₂N₂O₆	V = 2838.27 (10) Å³
M_r = 538.7	Z = 4
Monoclinic, C2/c	Cu Kα radiation
a = 15.4471 (3) Å	µ = 0.70 mm⁻¹
b = 8.8103 (2) Å	T = 120 K
c = 20.9374 (4) Å	0.38 × 0.28 × 0.20 mm
β = 95.077 (2)°

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	2533 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2157 reflections with I > 3σ(I)
T_min = 0.868, T_max = 1	R_int = 0.030
13938 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.73	Δρ_max = 0.20 e Å⁻³
2533 reflections	Δρ_min = −0.19 e Å⁻³
181 parameters

Special details top

Experimental. CrysAlisPro (Agilent Technologies, 2010) 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	0.16850 (6)	0.28700 (12)	0.16508 (5)	0.0355 (3)
O2	0.23006 (6)	0.43687 (10)	0.09549 (4)	0.0246 (3)
O3	0.47351 (6)	−0.13568 (10)	0.08411 (4)	0.0251 (3)
N1	0.45250 (4)	−0.23982 (9)	0.20231 (3)	0.0195 (3)
C1	0.5	−0.13860 (11)	0.25	0.0198 (5)
C2	0.45565 (8)	−0.39174 (13)	0.23189 (6)	0.0198 (4)
C3	0.44634 (8)	−0.52666 (14)	0.18685 (6)	0.0254 (4)
C4	0.45780 (9)	−0.67130 (15)	0.22757 (7)	0.0299 (4)
C5	0.36225 (8)	−0.19088 (14)	0.18416 (6)	0.0224 (4)
C6	0.35796 (8)	−0.04774 (14)	0.14442 (6)	0.0198 (3)
C7	0.29735 (8)	0.06379 (14)	0.15343 (6)	0.0207 (4)
C8	0.28954 (8)	0.19235 (14)	0.11452 (6)	0.0209 (4)
C9	0.34430 (8)	0.20849 (15)	0.06556 (6)	0.0219 (4)
C10	0.40580 (8)	0.09904 (15)	0.05580 (6)	0.0226 (4)
C11	0.41305 (8)	−0.02913 (14)	0.09496 (6)	0.0208 (4)
C12	0.22324 (8)	0.30676 (15)	0.12800 (6)	0.0227 (4)
C13	0.16944 (8)	0.55491 (14)	0.11005 (7)	0.0258 (4)
C14	0.17797 (8)	0.68569 (14)	0.06461 (6)	0.0235 (4)
C15	0.12183 (9)	0.81927 (15)	0.08138 (7)	0.0289 (4)
C16	0.12224 (10)	0.94748 (16)	0.03283 (7)	0.0347 (4)
H1a	0.540883	−0.078171	0.22915	0.0238*
H2	0.406857	−0.405328	0.256706	0.0237*
H3a	0.490696	−0.522444	0.157548	0.0305*
H3b	0.389436	−0.526022	0.164321	0.0305*
H4a	0.408928	−0.683029	0.252453	0.0359*
H4b	0.456989	−0.758307	0.19992	0.0359*
H5a	0.332944	−0.174885	0.222158	0.0269*
H5b	0.331366	−0.270607	0.16066	0.0269*
H7	0.259748	0.052498	0.18726	0.0249*
H9	0.339264	0.296369	0.038382	0.0263*
H10	0.443506	0.111227	0.022094	0.0271*
H13a	0.182864	0.588987	0.153344	0.0309*
H13b	0.111248	0.515806	0.104655	0.0309*
H14a	0.161007	0.653244	0.021541	0.0281*
H14b	0.23765	0.717093	0.066364	0.0281*
H15a	0.063247	0.785325	0.084261	0.0346*
H15b	0.141765	0.856808	0.123154	0.0346*
H16a	0.087619	1.030154	0.046201	0.0521*
H16b	0.180815	0.981529	0.029994	0.0521*
H16c	0.098561	0.911715	−0.00838	0.0521*
H3	0.4785 (11)	−0.193 (2)	0.1188 (9)	0.0376*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0375 (6)	0.0326 (6)	0.0388 (6)	0.0083 (4)	0.0174 (5)	0.0107 (4)
O2	0.0237 (4)	0.0207 (5)	0.0297 (5)	0.0030 (3)	0.0044 (4)	0.0042 (4)
O3	0.0297 (5)	0.0239 (5)	0.0220 (5)	0.0055 (4)	0.0045 (4)	0.0015 (4)
N1	0.0209 (5)	0.0171 (5)	0.0198 (5)	0.0000 (4)	−0.0019 (4)	0.0003 (4)
C1	0.0220 (8)	0.0160 (8)	0.0210 (8)	0	−0.0007 (7)	0
C2	0.0217 (6)	0.0169 (6)	0.0204 (6)	−0.0003 (5)	0.0007 (5)	0.0012 (5)
C3	0.0275 (6)	0.0205 (7)	0.0270 (7)	−0.0003 (5)	−0.0044 (5)	−0.0025 (5)
C4	0.0348 (8)	0.0188 (7)	0.0345 (7)	−0.0021 (5)	−0.0062 (6)	−0.0024 (5)
C5	0.0191 (6)	0.0228 (7)	0.0246 (6)	−0.0008 (5)	−0.0016 (5)	0.0045 (5)
C6	0.0197 (6)	0.0207 (6)	0.0180 (6)	−0.0040 (4)	−0.0036 (5)	0.0005 (5)
C7	0.0186 (6)	0.0238 (7)	0.0194 (6)	−0.0032 (5)	−0.0001 (5)	0.0010 (5)
C8	0.0217 (6)	0.0200 (7)	0.0202 (6)	−0.0025 (5)	−0.0015 (5)	0.0007 (5)
C9	0.0266 (6)	0.0201 (6)	0.0186 (6)	−0.0030 (5)	−0.0004 (5)	0.0018 (5)
C10	0.0263 (6)	0.0239 (7)	0.0177 (6)	−0.0014 (5)	0.0030 (5)	0.0005 (5)
C11	0.0207 (6)	0.0218 (7)	0.0193 (6)	−0.0013 (5)	−0.0019 (5)	−0.0031 (5)
C12	0.0236 (6)	0.0234 (7)	0.0209 (6)	−0.0013 (5)	−0.0002 (5)	0.0028 (5)
C13	0.0230 (6)	0.0229 (7)	0.0320 (7)	0.0032 (5)	0.0055 (5)	0.0006 (5)
C14	0.0237 (6)	0.0209 (7)	0.0251 (7)	−0.0001 (5)	−0.0011 (5)	0.0003 (5)
C15	0.0264 (7)	0.0222 (7)	0.0382 (8)	0.0002 (5)	0.0039 (6)	−0.0005 (6)
C16	0.0362 (8)	0.0239 (7)	0.0432 (8)	0.0042 (6)	−0.0019 (6)	0.0033 (6)

Geometric parameters (Å, º) top

O1—C12	1.2100 (17)	C6—C7	1.3816 (17)
O2—C12	1.3421 (15)	C6—C11	1.4070 (17)
O2—C13	1.4498 (16)	C7—C8	1.3943 (17)
O3—C11	1.3575 (15)	C7—H7	0.96
O3—H3	0.884 (18)	C8—C9	1.3928 (18)
N1—C1	1.4836 (9)	C8—C12	1.4818 (18)
N1—C2	1.4738 (14)	C9—C10	1.3815 (18)
N1—C5	1.4765 (13)	C9—H9	0.96
C1—H1a	0.96	C10—C11	1.3941 (17)
C1—H1aⁱ	0.96	C10—H10	0.96
C2—C2ⁱ	1.5061 (16)	C13—C14	1.5074 (18)
C2—C3	1.5163 (17)	C13—H13a	0.96
C2—H2	0.96	C13—H13b	0.96
C3—C4	1.5347 (18)	C14—C15	1.5213 (18)
C3—H3a	0.96	C14—H14a	0.96
C3—H3b	0.96	C14—H14b	0.96
C4—C4ⁱ	1.5381 (19)	C15—C16	1.520 (2)
C4—H4a	0.96	C15—H15a	0.96
C4—H4b	0.96	C15—H15b	0.96
C5—C6	1.5090 (17)	C16—H16a	0.96
C5—H5a	0.96	C16—H16b	0.96
C5—H5b	0.96	C16—H16c	0.96

C12—O2—C13	115.15 (10)	C8—C7—H7	119.2486
C11—O3—H3	105.7 (12)	C7—C8—C9	119.09 (11)
C1—N1—C2	105.49 (7)	C7—C8—C12	117.83 (11)
C1—N1—C5	113.40 (7)	C9—C8—C12	123.08 (11)
C2—N1—C5	111.64 (8)	C8—C9—C10	120.53 (11)
N1—C1—N1ⁱ	106.10 (7)	C8—C9—H9	119.7338
N1—C1—H1a	109.4715	C10—C9—H9	119.7345
N1—C1—H1aⁱ	109.4713	C9—C10—C11	119.93 (12)
N1ⁱ—C1—H1a	109.4713	C9—C10—H10	120.0369
N1ⁱ—C1—H1aⁱ	109.4715	C11—C10—H10	120.0376
H1a—C1—H1aⁱ	112.6412	O3—C11—C6	120.83 (11)
N1—C2—C2ⁱ	101.91 (9)	O3—C11—C10	118.84 (11)
N1—C2—C3	116.92 (9)	C6—C11—C10	120.33 (11)
N1—C2—H2	110.0241	O1—C12—O2	122.61 (12)
C2ⁱ—C2—C3	110.19 (10)	O1—C12—C8	123.94 (12)
C2ⁱ—C2—H2	116.771	O2—C12—C8	113.44 (11)
C3—C2—H2	101.7125	O2—C13—C14	108.75 (11)
C2—C3—C4	107.78 (10)	O2—C13—H13a	109.4715
C2—C3—H3a	109.471	O2—C13—H13b	109.4713
C2—C3—H3b	109.4714	C14—C13—H13a	109.4714
C4—C3—H3a	109.4714	C14—C13—H13b	109.4715
C4—C3—H3b	109.472	H13a—C13—H13b	110.1822
H3a—C3—H3b	111.1071	C13—C14—C15	111.23 (11)
C3—C4—C4ⁱ	112.90 (11)	C13—C14—H14a	109.4707
C3—C4—H4a	109.4707	C13—C14—H14b	109.4712
C3—C4—H4b	109.4703	C15—C14—H14a	109.4716
C4ⁱ—C4—H4a	109.4719	C15—C14—H14b	109.4715
C4ⁱ—C4—H4b	109.4713	H14a—C14—H14b	107.6531
H4a—C4—H4b	105.8086	C14—C15—C16	112.60 (12)
N1—C5—C6	112.36 (10)	C14—C15—H15a	109.4712
N1—C5—H5a	109.4714	C14—C15—H15b	109.4717
N1—C5—H5b	109.4706	C16—C15—H15a	109.4711
C6—C5—H5a	109.4712	C16—C15—H15b	109.4712
C6—C5—H5b	109.4714	H15a—C15—H15b	106.1546
H5a—C5—H5b	106.42	C15—C16—H16a	109.4718
C5—C6—C7	121.09 (11)	C15—C16—H16b	109.4721
C5—C6—C11	120.22 (11)	C15—C16—H16c	109.4718
C7—C6—C11	118.62 (11)	H16a—C16—H16b	109.4713
C6—C7—C8	121.50 (11)	H16a—C16—H16c	109.4705
C6—C7—H7	119.2469	H16b—C16—H16c	109.4698

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5a···O1ⁱⁱ	0.96	2.39	3.2393 (16)	148
O3—H3···N1	0.884 (18)	1.873 (18)	2.6859 (12)	152.0 (17)

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

Experimental details

Crystal data
Chemical formula	C₃₁H₄₂N₂O₆
M_r	538.7
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	15.4471 (3), 8.8103 (2), 20.9374 (4)
β (°)	95.077 (2)
V (Å³)	2838.27 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.38 × 0.28 × 0.20

Data collection
Diffractometer	Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.868, 1
No. of measured, independent and observed [I > 3σ(I)] reflections	13938, 2533, 2157
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.104, 1.73
No. of reflections	2533
No. of parameters	181
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

Computer programs: CrysAlis PRO (Agilent, 2010), SIR2002 (Burla et al., 2003), 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
C5—H5a···O1ⁱ	0.96	2.39	3.2393 (16)	147.73
O3—H3···N1	0.884 (18)	1.873 (18)	2.6859 (12)	152.0 (17)

Symmetry code: (i) −x+1/2, 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 Institutional Research Plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae Project of the Academy of Sciences of the Czech Republic. DQ acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Feng, Y. & Grant, D. J. W. (2006). Pharm. Res. 23, 1608–1616. Web of Science CrossRef PubMed CAS Google Scholar
Filarowski, A., Koll, A., Karpfen, A. & Wolschann, P. (2004). Chem. Phys. 297, 323–332. CrossRef CAS Google Scholar
Giordano, F., Bettini, R., Donini, C., Gazzaniga, A., Caira, M. R., Zhang, G. G. Z. & Grant, D. J. W. (1999). J. Pharm. Sci. 88, 1210–1216. CrossRef CAS Google Scholar
Koll, A., Parasuk, V., Parasuk, W., Karpfen, A. & Wolschann, P. (2001). J. Mol. Struct. 700, 81–90. Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic. Google Scholar
Rivera, A., Quiroga, D., Ríos-Motta, J., Dušek, M. & Fejfarová, K. (2010). Acta Cryst. E66, o2643. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rivera, A., Quiroga, D., Ríos-Motta, J., Dušek, M. & Fejfarová, K. (2011). Acta Cryst. E67, o1542. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2297

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di-n-butyl 4,4′-dihy­dr­oxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­­(methyl­ene)}dibenzoate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Di-n-butyl 4,4′-dihydroxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylene)}dibenzoate