4,4′-Dichloro-3,3′,5,5′-tetra­methyl-2,2′-[(3aR,7aR/3aS,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl)bis­(methyl­ene)]diphenol

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

doi:10.1107/S1600536811028960

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2131

doi:10.1107/S1600536811028960

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4,4′-Dichloro-3,3′,5,5′-tetramethyl-2,2′-[(3aR,7aR/3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl)bis(methylene)]diphenol

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 11 July 2011; accepted 18 July 2011; online 23 July 2011)

In the title compound, C₂₅H₃₂Cl₂N₂O₂, there are two intramolecular O—H⋯ N hydrogen-bonding interactions between the hydroxy groups on the aromatic rings and the two N atoms of the heterocyclic group. The cyclohexane ring adopts a chair conformation and the imidazolidine unit to which it is fused has a twisted envelope conformation. The asymmetric unit comprises one half-molecule which is completed by a twofold rotation axis. A C—H⋯O interaction is observed in the crystal structure.

Related literature

For related structures, see: Rivera et al. (2010 ); Cox (1995 ). For related quantum-chemical literature, see: Zierkiewicz et al. (2000 , 2003 , 2004 ).

Experimental

Crystal data

C₂₅H₃₂Cl₂N₂O₂
M_r = 463.4
Monoclinic, C 2/c
a = 16.6512 (7) Å
b = 9.6962 (3) Å
c = 14.4423 (6) Å
β = 98.892 (3)°
V = 2303.73 (15) Å³
Z = 4
Cu Kα radiation
μ = 2.73 mm⁻¹
T = 120 K
0.53 × 0.36 × 0.16 mm

Data collection

Agilent Xcalibur diffractometer with Atlas Gemini detector
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 )' T_min = 0.411, T_max = 0.734
32618 measured reflections
2054 independent reflections
1979 reflections with I > 3σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.116
S = 2.54
2054 reflections
144 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.827 (17)	1.880 (19)	2.6259 (13)	149.4 (19)
C12—H12B⋯O1ⁱ	0.96	2.56	3.4998 (17)	166
Symmetry code: (i) -x+1, -y+1, -z+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/S1600536811028960/go2020sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028960/go2020Isup2.hkl

checkCIF report

Comment top

The presence of p-halo substituent in the phenol ring afforded structural consequences such as the deformation of the ring observable in the bond distances and the bond angles values, which is related with the existence of resonance effect (X = Br, Cl) and inductive effect (X = F), according to theoretical results using the MP2 and density functional (B3LYP) methods (Zierkiewicz, et al. 2000 and 2003). Theoretical investigations using NBO analysis suggested that p-chloro substituent induces a decrease of electron density in the lone pair orbital of the O atom with a reinforcement of the delocalization of electronic density to aromatic ring observable in a slight shortening of C—O and C—C bonds (Zierkiewicz, et al. 2004). With the aim to understand the effect of electron-donating groups in the p-halophenol derivatives, we synthesized the title compound (I).

The molecular structure and atom-numbering scheme for (I) are shown in Fig. 1. Selected angles and bond lengths are listed in Table 1. These results show the existence of intramolecular hydrogen bonding interactions between the hydroxy H atom and the nitrogen atoms in the imidazolidine moiety. The shorter H—O distance (0.827 (17) Å) in comparison with the p-chlorophenol derivative (Rivera, et al. 2010), indicates a decreasing hydrogen-bonding strength. However, since the N···H and the N···O distances (table 1) are longer by 0.05 Å and 0.03 Å and the observed C—O bond length (1.3612 (17) Å) is in a good agreement with the mentioned related structure, we concluded that the methyl groups do not induce considerably the decrease in hydrogen-bonding strength despite the electron-donating effect on the aromatic rings.

However, the observed C1—C2 and C4—C5 bond length are longer in comparison with the 3,5-dimethyl-4-chlorophenol (Cox, 1995) and the p-chlorophenol derivative (Rivera, et al. 2010), indicating a lower tendency to form a quinoid-type structure, reducing the delocalization of electronic density presumably due the electron-donating effect of the methyl groups in the 3 and 5 positions.

Related literature top

For related structures, see: Rivera et al. (2010); Cox (1995). For related quantum-chemical literature, see: Zierkiewicz et al. (2000, 2003, 2004).

Experimental top

A solution of 3,5-dimethyl-4-chlorophenol (313 mg, 2.00 mmol) in dioxane (3 ml) was added dropwise to 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) prepared beforehand following previously described procedures, in dioxane (3 ml) and water (4 ml). The mixture was refluxed for about 8 h until precipitation of a colourless solid. The resulting solid was collected by filtration, washed with cool methanol and dried under vacuum (yield 50%, m.p. = 497–499 K). Single crystals of racemic (I) were grown from a CHCl₃ 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. Symmetry codes: i(-x, y, -z+1/2).

4,4'-Dichloro-3,3',5,5'-tetramethyl-2,2'-[(3aR,7aR/3aS, 7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3- diyl)bis(methylene)]diphenol top

Crystal data top

C₂₅H₃₂Cl₂N₂O₂	F(000) = 984
M_r = 463.4	D_x = 1.336 Mg m⁻³
Monoclinic, C2/c	Melting point: 498 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.5418 Å
a = 16.6512 (7) Å	Cell parameters from 23197 reflections
b = 9.6962 (3) Å	θ = 3.1–67°
c = 14.4423 (6) Å	µ = 2.73 mm⁻¹
β = 98.892 (3)°	T = 120 K
V = 2303.73 (15) Å³	Block, colourless
Z = 4	0.53 × 0.36 × 0.16 mm

Data collection top

Agilent Xcalibur diffractometer with Atlas Gemini detector	2054 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1979 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.046
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.2°, θ_min = 5.3°
Rotation method data acquisition using ω scans	h = −19→19
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)'	k = −11→11
T_min = 0.411, T_max = 0.734	l = −17→17
32618 measured reflections

Refinement top

Refinement on F²	61 constraints
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0016I²)
S = 2.54	(Δ/σ)_max = 0.010
2054 reflections	Δρ_max = 0.27 e Å⁻³
144 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint

Crystal data top

C₂₅H₃₂Cl₂N₂O₂	V = 2303.73 (15) Å³
M_r = 463.4	Z = 4
Monoclinic, C2/c	Cu Kα radiation
a = 16.6512 (7) Å	µ = 2.73 mm⁻¹
b = 9.6962 (3) Å	T = 120 K
c = 14.4423 (6) Å	0.53 × 0.36 × 0.16 mm
β = 98.892 (3)°

Data collection top

Agilent Xcalibur diffractometer with Atlas Gemini detector	2054 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)'	1979 reflections with I > 3σ(I)
T_min = 0.411, T_max = 0.734	R_int = 0.046
32618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 2.54	Δρ_max = 0.27 e Å⁻³
2054 reflections	Δρ_min = −0.24 e Å⁻³
144 parameters

Special details top

Experimental. ¹H NMR (CDCl3, 400 MHz): δ 1.31 (4H, m), 1.87 (2H, m), 2.08 (2H, m), 2.26 (2H, s, ArCH3), 2.28 (2H, s, ArCH3), 2.36 (2H, m), 2.46 (2H, s, NCH2N), 3.68 (2H, d, 2J = 14.0 Hz, ArCH2N), 4.05 (2H, d, 2J = 14.0 Hz, ArCH2N), 6.57 (2H, s), 11.18 (2H, bs). 13C NMR (CDCl3, 100 MHz): δ 16.7, 21.0, 24.0, 28.9, 53.0, 69.2, 75.8, 116.4, 118.3, 125.4, 133.5, 136.7, 155.9.

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
Cl1	0.76734 (2)	−0.07704 (4)	0.93216 (3)	0.03586 (17)
O1	0.53003 (6)	0.35475 (10)	0.97680 (7)	0.0322 (3)
N1	0.55223 (4)	0.45810 (9)	0.81461 (5)	0.0204 (3)
C1	0.63836 (7)	0.27435 (13)	0.89563 (9)	0.0222 (4)
C2	0.69590 (8)	0.17091 (14)	0.88695 (9)	0.0241 (4)
C3	0.69590 (8)	0.05287 (14)	0.94211 (9)	0.0258 (4)
C4	0.64130 (8)	0.03133 (14)	1.00472 (9)	0.0261 (4)
C5	0.58507 (9)	0.13507 (14)	1.01187 (9)	0.0264 (4)
C6	0.58435 (8)	0.25638 (14)	0.96017 (9)	0.0247 (4)
C7	0.75806 (9)	0.18747 (17)	0.82207 (11)	0.0348 (5)
C8	0.64127 (10)	−0.09641 (15)	1.06364 (10)	0.0326 (4)
C9	0.63587 (8)	0.40679 (14)	0.83881 (9)	0.0237 (4)
C10	0.5	0.36595 (10)	0.75	0.0261 (5)
C11	0.54490 (7)	0.59416 (13)	0.76934 (8)	0.0197 (4)
C12	0.56829 (8)	0.71792 (13)	0.83144 (9)	0.0231 (4)
C13	0.54453 (8)	0.84894 (13)	0.77370 (9)	0.0267 (4)
H1	0.5257 (13)	0.4090 (18)	0.9321 (12)	0.0387*
H5	0.545829	0.122861	1.053384	0.0317*
H7a	0.810554	0.160357	0.854033	0.0522*
H7b	0.743354	0.130427	0.767765	0.0522*
H7c	0.759828	0.28218	0.803107	0.0522*
H8a	0.694459	−0.110125	1.098872	0.0488*
H8b	0.6025	−0.08608	1.105925	0.0488*
H8c	0.626841	−0.174614	1.023772	0.0488*
H9a	0.668777	0.475635	0.874286	0.0284*
H9b	0.658249	0.390095	0.782437	0.0284*
H10	0.533179	0.311486	0.715257	0.0313*
H11	0.582025	0.604471	0.725135	0.0237*
H12a	0.625937	0.717436	0.852045	0.0277*
H12b	0.539438	0.71524	0.884052	0.0277*
H13a	0.57933	0.859112	0.726983	0.032*
H13b	0.554553	0.928472	0.813392	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0336 (3)	0.0301 (3)	0.0424 (3)	0.01390 (13)	0.00143 (18)	−0.00539 (13)
O1	0.0418 (6)	0.0280 (5)	0.0313 (5)	0.0149 (4)	0.0196 (4)	0.0086 (4)
N1	0.0172 (5)	0.0215 (5)	0.0224 (5)	0.0011 (4)	0.0029 (4)	0.0007 (4)
C1	0.0201 (6)	0.0247 (7)	0.0209 (6)	0.0021 (5)	0.0003 (5)	−0.0019 (5)
C2	0.0202 (6)	0.0272 (7)	0.0235 (6)	0.0018 (5)	−0.0006 (5)	−0.0065 (5)
C3	0.0231 (7)	0.0245 (6)	0.0274 (7)	0.0061 (5)	−0.0035 (5)	−0.0075 (5)
C4	0.0307 (7)	0.0235 (7)	0.0217 (6)	0.0032 (5)	−0.0032 (5)	−0.0050 (5)
C5	0.0321 (7)	0.0258 (7)	0.0218 (6)	0.0046 (5)	0.0058 (5)	0.0003 (5)
C6	0.0271 (7)	0.0258 (6)	0.0217 (6)	0.0056 (5)	0.0049 (5)	−0.0019 (5)
C7	0.0263 (7)	0.0401 (8)	0.0393 (8)	0.0072 (6)	0.0096 (6)	−0.0021 (6)
C8	0.0404 (8)	0.0252 (7)	0.0301 (7)	0.0048 (6)	−0.0010 (6)	0.0001 (5)
C9	0.0177 (6)	0.0283 (7)	0.0253 (6)	0.0024 (5)	0.0045 (5)	0.0008 (5)
C10	0.0257 (9)	0.0216 (9)	0.0297 (9)	0	0.0002 (7)	0
C11	0.0196 (7)	0.0223 (6)	0.0180 (6)	−0.0001 (4)	0.0052 (5)	0.0006 (4)
C12	0.0234 (6)	0.0241 (7)	0.0219 (6)	−0.0010 (5)	0.0037 (5)	−0.0006 (5)
C13	0.0324 (8)	0.0225 (6)	0.0254 (6)	−0.0027 (5)	0.0051 (6)	−0.0004 (5)

Geometric parameters (Å, º) top

O1—C6	1.3612 (17)	C7—H7c	0.96
O1—H1	0.827 (17)	C8—H8a	0.96
N1—C9	1.4694 (15)	C8—H8b	0.96
N1—C10	1.4746 (10)	C8—H8c	0.96
N1—C11	1.4691 (15)	C9—H9a	0.96
C1—C2	1.4059 (19)	C9—H9b	0.96
C1—C6	1.4026 (19)	C10—H10	0.96
C1—C9	1.5211 (19)	C10—H10ⁱ	0.96
C2—C3	1.3945 (19)	C11—C11ⁱ	1.5132 (16)
C2—C7	1.508 (2)	C11—C12	1.5127 (17)
C3—C4	1.394 (2)	C11—H11	0.96
C4—C5	1.389 (2)	C12—C13	1.5376 (18)
C4—C8	1.503 (2)	C12—H12a	0.96
C5—C6	1.3923 (19)	C12—H12b	0.96
C5—H5	0.96	C13—C13ⁱ	1.5341 (18)
C7—H7a	0.96	C13—H13a	0.96
C7—H7b	0.96	C13—H13b	0.96

C6—O1—H1	106.8 (14)	H8b—C8—H8c	109.4716
C9—N1—C10	112.95 (8)	N1—C9—C1	111.10 (10)
C9—N1—C11	114.86 (9)	N1—C9—H9a	109.4708
C10—N1—C11	105.20 (7)	N1—C9—H9b	109.4711
C2—C1—C6	119.11 (12)	C1—C9—H9a	109.4716
C2—C1—C9	121.08 (12)	C1—C9—H9b	109.4713
C6—C1—C9	119.77 (12)	H9a—C9—H9b	107.791
C1—C2—C3	118.31 (12)	N1—C10—N1ⁱ	105.41 (8)
C1—C2—C7	121.47 (12)	N1—C10—H10	109.4714
C3—C2—C7	120.20 (12)	N1—C10—H10ⁱ	109.471
C2—C3—C4	123.46 (13)	N1ⁱ—C10—H10	109.471
C3—C4—C5	117.04 (12)	N1ⁱ—C10—H10ⁱ	109.4714
C3—C4—C8	123.25 (13)	H10—C10—H10ⁱ	113.2497
C5—C4—C8	119.71 (13)	N1—C11—C11ⁱ	100.00 (9)
C4—C5—C6	121.47 (13)	N1—C11—C12	116.90 (9)
C4—C5—H5	119.2656	N1—C11—H11	111.8254
C6—C5—H5	119.2654	C11ⁱ—C11—C12	111.59 (10)
O1—C6—C1	122.83 (12)	C11ⁱ—C11—H11	117.1086
O1—C6—C5	116.63 (12)	C12—C11—H11	100.2818
C1—C6—C5	120.53 (13)	C11—C12—C13	108.22 (10)
C2—C7—H7a	109.4708	C11—C12—H12a	109.4707
C2—C7—H7b	109.4713	C11—C12—H12b	109.4717
C2—C7—H7c	109.4707	C13—C12—H12a	109.4709
H7a—C7—H7b	109.4715	C13—C12—H12b	109.4717
H7a—C7—H7c	109.4716	H12a—C12—H12b	110.6913
H7b—C7—H7c	109.4714	C12—C13—C13ⁱ	113.08 (11)
C4—C8—H8a	109.4711	C12—C13—H13a	109.4717
C4—C8—H8b	109.4712	C12—C13—H13b	109.4711
C4—C8—H8c	109.471	C13ⁱ—C13—H13a	109.4708
H8a—C8—H8b	109.472	C13ⁱ—C13—H13b	109.472
H8a—C8—H8c	109.4704	H13a—C13—H13b	105.6049

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.827 (17)	1.880 (19)	2.6259 (13)	149.4 (19)
C12—H12B···O1ⁱⁱ	0.96	2.56	3.4998 (17)	166

Symmetry code: (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₅H₃₂Cl₂N₂O₂
M_r	463.4
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	16.6512 (7), 9.6962 (3), 14.4423 (6)
β (°)	98.892 (3)
V (Å³)	2303.73 (15)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.73
Crystal size (mm)	0.53 × 0.36 × 0.16

Data collection
Diffractometer	Agilent Xcalibur diffractometer with Atlas Gemini detector
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2010)'
T_min, T_max	0.411, 0.734
No. of measured, independent and observed [I > 3σ(I)] reflections	32618, 2054, 1979
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.116, 2.54
No. of reflections	2054
No. of parameters	144
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.24

Computer programs: CrysAlis PRO (Agilent, 2010), 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
O1—H1···N1	0.827 (17)	1.880 (19)	2.6259 (13)	149.4 (19)
C12—H12B···O1ⁱ	0.96	2.56	3.4998 (17)	166

Symmetry code: (i) −x+1, −y+1, −z+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 the project Praemium Academiae of the Academy of Sciences of the Czech Republic. DQ acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2131

doi:10.1107/S1600536811028960

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

4,4′-Di­chloro-3,3′,5,5′-tetra­methyl-2,2′-[(3aR,7aR/3aS,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl)bis­­(methyl­ene)]diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,4′-Dichloro-3,3′,5,5′-tetramethyl-2,2′-[(3aR,7aR/3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl)bis(methylene)]diphenol