4,4′-Dibromo-2,2′-{[(3aS,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­idene)}diphenol

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

doi:10.1107/S1600536811006489

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o753

doi:10.1107/S1600536811006489

Open

access

4,4′-Dibromo-2,2′-{[(3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylidene)}diphenol

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

^aDepartamento de Química, Universidad Nacional de Colombia, Bogotá, AA 14490, 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 9 February 2011; accepted 21 February 2011; online 2 March 2011)

The cyclohexane ring in the title compound, C₂₁H₂₄Br₂N₂O₂, adopts a chair conformation and the five-membered ring to which it is fused has a twisted envelope conformation. The asymmetric unit contains one half-molecule, which is related to the other half by a twofold rotation axis. The two N atoms of the five-membered ring are linked to the hydroxy groups by intramolecular O—H⋯N hydrogen bonds. In the crystal, intermolecular C—H⋯O and C—H⋯π interactions occur.

Related literature

For a related structure, see: Rivera et al. (2010 ). For uses of di-Mannich bases, see: Mitra et al. (2006 ).

Experimental

Crystal data

C₂₁H₂₄Br₂N₂O₂
M_r = 496.2
Orthorhombic, P 2₁ 2₁ 2
a = 5.9645 (2) Å
b = 18.5497 (4) Å
c = 9.0494 (2) Å
V = 1001.22 (5) Å³
Z = 2
Cu Kα radiation
μ = 5.32 mm⁻¹
T = 120 K
0.19 × 0.13 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas detector
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.454, T_max = 0.678
17493 measured reflections
1749 independent reflections
1739 reflections with I > 3σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.015
wR(F²) = 0.049
S = 1.21
1749 reflections
126 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.12 e Å⁻³
Absolute structure: Flack (1983 ), 670 Friedel pairs
Flack parameter: 0.008 (20)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.833 (19)	1.905 (18)	2.6506 (13)	148.3 (19)
C1—H1a⋯O1ⁱ	0.96	2.57	3.3351 (11)	137
C8—H8⋯Cg2ⁱⁱ	0.96	2.85	3.5407 (16)	130
C11—H11b⋯Cg2ⁱⁱⁱ	0.96	2.86	3.728 (2)	150
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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/S1600536811006489/ng5118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006489/ng5118Isup2.hkl

checkCIF report

Comment top

The title compound was obtained by reaction of racemic cyclic aminal (2R,7R,11S,16S)-1,8,10,17-tetraazapentacyclo[8.8.1.1^8,17.0^2,7.0^11,16]icosane with p-bromophenol. The molecular structure and atom-numbering scheme for (I) are shown in Fig. 1. Selected angles and bond lengths are listed in Table 1. Its X-ray structure confirms the presence of intramolecular hydrogen bonds between the phenolic hydroxyl groups and nitrogen atoms [N—H, 1.903 (18) Å] that is however by 0.13 Å longer in comparison with related structure (Rivera et al., 2010), whereas the N···O distance [2.6506 (14) Å] is in good agreement with the one found in related structure [2.652 (2) Å]. Similar to this related structure, the observed C—O bond length [1.353 (2) Å] is considerably shortened in relation to other Mannich bases.

In the title compound, C₂₁H₂₄Br₂N₂O₂, the asymmetric unit contains one-half of the molecule, which is related to the other half by a twofold rotation axis [symmetry code: - x, y, -z] passing through C1. The orthorhombic unit cell contains two molecules. Instead, the molecules have identical (S,S)-molecular configuration and its absolute structure was determined with a Flack parameter of 0.01 (2) (Flack, 1983).

Related literature top

For a related structure, see: Rivera et al. (2010). For uses of di-Mannich bases, see: Mitra et al. (2006).

Experimental top

Physical Measurements

The melting point was determined with an Electrothermal apparatus, and it has not been corrected. IR spectrum was recorded as KBr pellets at 292 K on a Perkin-Elmer Paragon FT—IR instrument. NMR spectra were performed in CDCl₃ at room temperature on a Bruker AMX 400 Advance spectrometer.

Preparation of 4,4'-Dibromo-2,2'-(3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3- benzimidazole-1,3-diyl)bis(methylene)]diphenol) (I)

A solution of (2R,7R,11S,16S)-1,8,10,17-tetraazapentacyclo[8.8.1.^18,17.0^2,7.0^11,16]icosane (3) (276 mg, 1.00 mmol) in dioxane (3 ml) and water (4 ml), prepared beforehand following previously described procedures, was added dropwise in a dioxane solution (3 ml) containing two equivalents of p-bromophenol (346 mg, 2.00 mmol) in a two-necked round-bottomed flask. The mixture was refluxed for about 6 h until precipitation of a colourless solid. The resulting solid was collected by filtration, washed with cool methanol and dried under vacuum (yield 47%, m.p. = 497–499 K). Next, the crude product (100 mg, 0.202 mmol) was dissolved in 5 ml of a 4:1 mixture of chloroform: methanol. Single crystals of title compound (I) suitable for X-ray analysis were grown by slow evaporation of the solvent at room temperature over a period of about 2 weeks in a preferential crystallization (yield 35%). ¹H NMR (CDCl₃, 400 MHz): δ 1.27 (4H, m), 1.85 (2H, m), 2.05 (2H, m), 2.33 (2H, m), 3.41 (2H, d, J = 14.0 Hz, ArCH₂N), 3.51 (2H, s, NCH₂N), 4.14 (2H, d, J = 14.0 Hz, ArCH₂N), 6.69 (2H, d, J = 8.8 Hz), 7.06 (2H, s), 7.24 (2H, d, J = 8.8 Hz). ¹³C NMR (CDCl₃, 100 MHz): δ 23.9, 28.9, 55.8, 69.1, 75.7, 111.1, 118.1, 123.4, 130.6, 131.8, 156.6.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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. Ellipsoid plot of the title compound. Displacement ellipsoids are drawn at 50% probability level. [Symmetry codes: (i) 1-x, 1-y, z.]
	Fig. 2. Hydrogen bonding of the molecules of the title compound viewed along c.

4,4'-Dibromo-2,2'-{[(3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro- 1H-1,3-benzimidazole-1,3-diyl]bis(methylidene)}diphenol top

Crystal data top

C₂₁H₂₄Br₂N₂O₂	F(000) = 500
M_r = 496.2	D_x = 1.646 Mg m⁻³
Orthorhombic, P2₁2₁2	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2 2ab	Cell parameters from 16248 reflections
a = 5.9645 (2) Å	θ = 4.8–66.5°
b = 18.5497 (4) Å	µ = 5.32 mm⁻¹
c = 9.0494 (2) Å	T = 120 K
V = 1001.22 (5) Å³	Prism, colorless
Z = 2	0.19 × 0.13 × 0.10 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with an Atlas detector	1749 independent reflections
Radiation source: X-ray tube	1739 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.022
Detector resolution: 10.3784 pixels mm^-1	θ_max = 66.8°, θ_min = 4.8°
Rotation method data acquisition using ω scans	h = −7→6
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→10
T_min = 0.454, T_max = 0.678	l = −21→21
17493 measured reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.015	Weighting scheme based on measured s.u.'s w = 1/[σ²(I) + 0.0016I²]
wR(F²) = 0.049	(Δ/σ)_max = 0.001
S = 1.21	Δρ_max = 0.11 e Å⁻³
1749 reflections	Δρ_min = −0.12 e Å⁻³
126 parameters	Absolute structure: Flack (1983), 670 Friedel pairs
1 restraint	Absolute structure parameter: 0.008 (20)
45 constraints

Crystal data top

C₂₁H₂₄Br₂N₂O₂	V = 1001.22 (5) Å³
M_r = 496.2	Z = 2
Orthorhombic, P2₁2₁2	Cu Kα radiation
a = 5.9645 (2) Å	µ = 5.32 mm⁻¹
b = 18.5497 (4) Å	T = 120 K
c = 9.0494 (2) Å	0.19 × 0.13 × 0.10 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with an Atlas detector	1749 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	1739 reflections with I > 3σ(I)
T_min = 0.454, T_max = 0.678	R_int = 0.022
17493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.015	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.049	Δρ_max = 0.11 e Å⁻³
S = 1.21	Δρ_min = −0.12 e Å⁻³
1749 reflections	Absolute structure: Flack (1983), 670 Friedel pairs
126 parameters	Absolute structure parameter: 0.008 (20)
1 restraint

Special details top

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
Br1	0.55638 (3)	0.229059 (8)	0.146172 (18)	0.02610 (7)
O1	0.99958 (19)	0.42005 (6)	0.59844 (13)	0.0226 (3)
N1	0.59652 (10)	0.44416 (5)	0.71146 (11)	0.0163 (4)
C1	0.5	0.5	0.61175 (12)	0.0154 (6)
C2	0.5511 (3)	0.36959 (8)	0.66196 (17)	0.0165 (4)
C3	0.6757 (3)	0.35153 (7)	0.52184 (17)	0.0156 (4)
C4	0.8947 (3)	0.37777 (8)	0.49815 (18)	0.0174 (4)
C5	1.0085 (3)	0.35992 (9)	0.36866 (19)	0.0204 (4)
C6	0.9120 (3)	0.31499 (8)	0.26478 (18)	0.0205 (5)
C7	0.6975 (3)	0.28860 (8)	0.29074 (18)	0.0180 (4)
C8	0.5810 (2)	0.30615 (8)	0.41680 (17)	0.0160 (4)
C9	0.5029 (3)	0.45921 (8)	0.85825 (17)	0.0179 (4)
C10	0.6319 (3)	0.43125 (9)	0.99165 (18)	0.0268 (5)
C11	0.5129 (4)	0.45880 (10)	1.13117 (19)	0.0322 (6)
H1a	0.382527	0.479008	0.553376	0.0185*
H2a	0.39302	0.363598	0.646178	0.0198*
H2b	0.593539	0.336399	0.738387	0.0198*
H5	1.155662	0.379087	0.351434	0.0245*
H6	0.991627	0.302257	0.176355	0.0245*
H8	0.433442	0.286947	0.43234	0.0192*
H9	0.362416	0.434666	0.870296	0.0214*
H10a	0.782412	0.449589	0.989185	0.0322*
H10b	0.63082	0.3795	0.991145	0.0322*
H11a	0.5957	0.444143	1.217041	0.0386*
H11b	0.367722	0.43676	1.138666	0.0386*
H1o	0.904 (3)	0.4361 (12)	0.657 (2)	0.0272*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03375 (13)	0.02617 (12)	0.01839 (12)	−0.00261 (7)	−0.00326 (7)	−0.00361 (7)
O1	0.0184 (6)	0.0183 (5)	0.0312 (7)	−0.0015 (4)	−0.0002 (5)	−0.0041 (5)
N1	0.0203 (7)	0.0104 (6)	0.0182 (7)	0.0013 (5)	0.0010 (5)	−0.0010 (5)
C1	0.0145 (10)	0.0119 (9)	0.0197 (10)	0.0006 (7)	0	0
C2	0.0189 (7)	0.0107 (7)	0.0199 (7)	−0.0017 (5)	0.0040 (7)	−0.0010 (6)
C3	0.0185 (7)	0.0095 (6)	0.0188 (7)	0.0034 (6)	0.0013 (6)	0.0036 (6)
C4	0.0176 (7)	0.0110 (7)	0.0236 (8)	0.0019 (5)	−0.0012 (6)	0.0012 (6)
C5	0.0174 (7)	0.0167 (7)	0.0271 (8)	0.0016 (6)	0.0032 (6)	0.0049 (7)
C6	0.0229 (9)	0.0184 (7)	0.0201 (8)	0.0063 (6)	0.0029 (6)	0.0046 (6)
C7	0.0243 (8)	0.0134 (6)	0.0165 (8)	0.0034 (6)	−0.0013 (6)	0.0005 (6)
C8	0.0143 (7)	0.0119 (7)	0.0220 (8)	0.0018 (5)	−0.0021 (6)	0.0023 (6)
C9	0.0215 (8)	0.0153 (8)	0.0169 (7)	0.0023 (5)	0.0009 (6)	0.0022 (6)
C10	0.0437 (10)	0.0176 (7)	0.0191 (8)	0.0094 (6)	−0.0006 (8)	0.0008 (7)
C11	0.0521 (12)	0.0251 (10)	0.0193 (8)	0.0110 (8)	0.0014 (9)	0.0042 (7)

Geometric parameters (Å, º) top

Br1—C7	1.9080 (16)	C5—H5	0.96
O1—C4	1.353 (2)	C6—C7	1.390 (2)
O1—H1o	0.84 (2)	C6—H6	0.96
N1—C1	1.4895 (12)	C7—C8	1.375 (2)
N1—C2	1.4789 (18)	C8—H8	0.96
N1—C9	1.4677 (18)	C9—C9ⁱ	1.514 (2)
C1—H1a	0.96	C9—C10	1.523 (2)
C1—H1aⁱ	0.96	C9—H9	0.96
C2—C3	1.507 (2)	C10—C11	1.536 (3)
C2—H2a	0.96	C10—H10a	0.96
C2—H2b	0.96	C10—H10b	0.96
C3—C4	1.410 (2)	C11—C11ⁱ	1.536 (3)
C3—C8	1.390 (2)	C11—H11a	0.96
C4—C5	1.394 (2)	C11—H11b	0.96
C5—C6	1.382 (2)

C4—O1—H1o	108.6 (14)	C5—C6—H6	120.6356
C1—N1—C2	113.34 (9)	C7—C6—H6	120.636
C1—N1—C9	105.60 (9)	Br1—C7—C6	119.62 (12)
C2—N1—C9	112.48 (10)	Br1—C7—C8	118.88 (12)
N1—C1—N1ⁱ	105.43 (9)	C6—C7—C8	121.48 (15)
N1—C1—H1a	109.4713	C3—C8—C7	120.37 (14)
N1—C1—H1aⁱ	109.4712	C3—C8—H8	119.8142
N1ⁱ—C1—H1a	109.4712	C7—C8—H8	119.8142
N1ⁱ—C1—H1aⁱ	109.4713	N1—C9—C9ⁱ	101.48 (12)
H1a—C1—H1aⁱ	113.2317	N1—C9—C10	117.42 (13)
N1—C2—C3	111.86 (12)	N1—C9—H9	110.1556
N1—C2—H2a	109.4713	C9ⁱ—C9—C10	110.62 (13)
N1—C2—H2b	109.4715	C9ⁱ—C9—H9	117.0073
C3—C2—H2a	109.471	C10—C9—H9	100.9265
C3—C2—H2b	109.4709	C9—C10—C11	107.74 (15)
H2a—C2—H2b	106.9725	C9—C10—H10a	109.471
C2—C3—C4	120.52 (13)	C9—C10—H10b	109.4714
C2—C3—C8	120.64 (14)	C11—C10—H10a	109.4709
C4—C3—C8	118.78 (14)	C11—C10—H10b	109.4716
O1—C4—C3	121.76 (14)	H10a—C10—H10b	111.1472
O1—C4—C5	118.47 (13)	C10—C11—C11ⁱ	112.17 (15)
C3—C4—C5	119.78 (14)	C10—C11—H11a	109.4713
C4—C5—C6	120.83 (14)	C10—C11—H11b	109.4711
C4—C5—H5	119.5819	C11ⁱ—C11—H11a	109.4712
C6—C5—H5	119.5833	C11ⁱ—C11—H11b	109.4713
C5—C6—C7	118.73 (15)	H11a—C11—H11b	106.632

C2—N1—C1—N1ⁱ	138.00 (9)	O1—C4—C5—C6	177.87 (15)
C9—N1—C1—N1ⁱ	14.44 (9)	C3—C4—C5—C6	−1.9 (2)
C1—N1—C2—C3	68.53 (14)	C4—C5—C6—C7	0.9 (2)
C9—N1—C2—C3	−171.77 (12)	C5—C6—C7—Br1	177.93 (12)
C1—N1—C9—C10	−157.29 (11)	C5—C6—C7—C8	−0.1 (2)
C1—N1—C9—C9ⁱ	−36.62 (13)	Br1—C7—C8—C3	−177.66 (11)
C2—N1—C9—C10	78.61 (16)	C6—C7—C8—C3	0.4 (2)
C2—N1—C9—C9ⁱ	−160.72 (12)	N1—C9—C10—C11	175.39 (13)
N1—C2—C3—C4	37.37 (19)	C9ⁱ—C9—C10—C11	59.64 (18)
N1—C2—C3—C8	−145.54 (13)	N1—C9—C9ⁱ—N1ⁱ	45.12 (14)
C2—C3—C4—O1	−0.5 (2)	N1—C9—C9ⁱ—C10ⁱ	170.46 (12)
C2—C3—C4—C5	179.31 (14)	C10—C9—C9ⁱ—N1ⁱ	170.46 (12)
C8—C3—C4—O1	−177.62 (14)	C10—C9—C9ⁱ—C10ⁱ	−64.21 (18)
C8—C3—C4—C5	2.2 (2)	C9—C10—C11—C11ⁱ	−55.1 (2)
C2—C3—C8—C7	−178.55 (14)	C10—C11—C11ⁱ—C10ⁱ	54.8 (2)
C4—C3—C8—C7	−1.4 (2)

Symmetry code: (i) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.833 (19)	1.905 (18)	2.6506 (13)	148.3 (19)
C1—H1a···O1ⁱⁱ	0.96	2.57	3.3351 (11)	137
C8—H8···Cg2ⁱⁱⁱ	0.96	2.85	3.5407 (16)	130
C11—H11b···Cg2^iv	0.96	2.86	3.728 (2)	150

Symmetry codes: (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄Br₂N₂O₂
M_r	496.2
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	120
a, b, c (Å)	5.9645 (2), 18.5497 (4), 9.0494 (2)
V (Å³)	1001.22 (5)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	5.32
Crystal size (mm)	0.19 × 0.13 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with an Atlas detector
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.454, 0.678
No. of measured, independent and observed [I > 3σ(I)] reflections	17493, 1749, 1739
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.049, 1.21
No. of reflections	1749
No. of parameters	126
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)	0.11, −0.12
Absolute structure	Flack (1983), 670 Friedel pairs
Absolute structure parameter	0.008 (20)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.833 (19)	1.905 (18)	2.6506 (13)	148.3 (19)
C1—H1a···O1ⁱ	0.96	2.57	3.3351 (11)	137
C8—H8···Cg2ⁱⁱ	0.96	2.85	3.5407 (16)	130
C11—H11b···Cg2ⁱⁱⁱ	0.96	2.86	3.728 (2)	150

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z; (iii) x, y+1, z.

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

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
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Mitra, A., Harvey, M. J., Proffitt, M. K., DePue, L. J., Parkin, S. & Atwood, D. A. (2006). J. Organomet. Chem. 69, 523–528. Web of Science CSD CrossRef Google Scholar
Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o753

doi:10.1107/S1600536811006489

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4,4′-Di­bromo-2,2′-{[(3aS,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­­(methyl­­idene)}diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,4′-Dibromo-2,2′-{[(3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylidene)}diphenol