organic compounds
2-[(1H-Benzimidazol-1-yl)methyl]phenol benzene hemisolvate
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, Max-von-Laue-Strasse 7, Frankfurt/Main, D-60438, Germany
*Correspondence e-mail: ariverau@unal.edu.co
In the title solvate, C14H12N2O·0.5C6H6, the complete benzene molecule is generated by a crystallographic inversion centre. The dihedral angle between the planes of the benzimidazole moiety and the phenol substituent is 75.28 (3)°. In the crystal, O—H⋯N hydrogen bonds link the molecules into parallel chains propagating along [100]. The molecules are further connected by C—H⋯π interactions.
CCDC reference: 981330
Related literature
For related structures, see: Cai et al. (2006); Rivera et al. (2012); Shi et al. (2011). For another synthesis procedure, see: Milata et al. (2001); Rivera et al. (2008). For the pharmacological use of benzimidazoles, see: Alamgir et al. (2007). For C—H⋯π interactions, see: Malathy Sony & Ponnuswamy (2005).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2001); cell X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 981330
10.1107/S1600536814000841/sj5381sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000841/sj5381Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000841/sj5381Isup3.cml
Appropriately substituted benzimidazole derivatives have found diverse therapeutic applications as antiulcer, antihypertensive, antiviral, antifungal, anticancer, and antihistaminic agents [Alamgir et al. 2007]. Although the synthesis of the title compound has been reported in the literature (Milata et al., 2001; Rivera et al., 2008), we have developed an alternative route to prepare this compound starting from N1,N2-bis((1H-benzotriazol-1-yl)methyl)benzene-1,2- diamine.
The π interaction according to the literature (Malathy Sony et al. 2005). The dihedral angle between the phenol substitutent and the benzimidazole ring [75.28 (3)°] is similar to the one in a related structure (Cai et al., 2006). In the benzimidazole moiety, the bond distances and angles are in good agreement with those found in bis(1H-benzimidazol-1-yl)methane monohydrate (Shi et al., 2011), 1-(6-chloropyridin-3-ylmethyl)-1H-benzimidazole (Cai et al., 2006) and (1H-benzimidazol-1-yl)methanol (Rivera et al., 2012).
contains one molecule of 2-((1H-benzimidazol-1-yl)methyl)phenol and half a molecule of benzene (Fig. 1). The solvent molecule subtends a dihedral angle of 78.90 (6)° with respect to the phenol substituent and 70.99 (6)° with respect to the benzimidazole moiety, which suggest an edge-to-face (T-shaped) C—H···An intermolecular hydrogen bond was observed in the crystal packing (Fig. 2) between the hydroxyl group of one molecule and a nitrogen atom of another one (Table 1). The O—H distance is longer than in (1H-benzimidazol-1-yl)methanol [0.894 (19)Å] (Rivera et al., 2012). However, the O···N distance [2.7200 (16)Å and 2.7355 (16)Å] and the O—H···N angle [174 (2)°, 173.8 (17)°] are similar in both structures. The O—H···N hydrogen bond connects the molecules forming chains running along the a-axis. The benzene molecule is linked to molecules of 2-((1H-benzimidazol-1-yl)methyl)phenol via C—H···π interactions (Fig. 3) acting as both a donor and an acceptor, Table 1. The benzimidazole moiety also forms two C—H···π interactions to the phenol rings of neighbouring molecules. These values are is similar to the values reported for other C—H···π interactions (Malathy Sony et al. 2005).
A mixture of phenol (0.282 g, 3.00 mmol) and N1,N2-bis((1H-benzotriazol-1-yl)methyl)benzene-1,2-diamine (0.370 g, 1.00 mmol) was heated to 160 °C, after 5 minutes the mixture was cooled at room temperature until a sticky residue appeared. The product was purified by
using a mixture of benzene: ethyl acetate (80:20) as the mobile phase (yield 25 %, m.p.= 489-490 K). Single crystals were grown from a benzene:ethyl acetate solution by slow evaporation of the solvent at room temperature over a period of about one week.All H atoms were located in a difference map. The hydroxyl H atom was freely refined. H atoms bonded to C atoms were refined using a riding model, with secondary C—H = 0.99 Å and aromatic C—H = 0.95 Å and with Uiso(H) = 1.2Ueq(C).
Appropriately substituted benzimidazole derivatives have found diverse therapeutic applications as antiulcer, antihypertensive, antiviral, antifungal, anticancer, and antihistaminic agents [Alamgir et al. 2007]. Although the synthesis of the title compound has been reported in the literature (Milata et al., 2001; Rivera et al., 2008), we have developed an alternative route to prepare this compound starting from N1,N2-bis((1H-benzotriazol-1-yl)methyl)benzene-1,2- diamine.
The π interaction according to the literature (Malathy Sony et al. 2005). The dihedral angle between the phenol substitutent and the benzimidazole ring [75.28 (3)°] is similar to the one in a related structure (Cai et al., 2006). In the benzimidazole moiety, the bond distances and angles are in good agreement with those found in bis(1H-benzimidazol-1-yl)methane monohydrate (Shi et al., 2011), 1-(6-chloropyridin-3-ylmethyl)-1H-benzimidazole (Cai et al., 2006) and (1H-benzimidazol-1-yl)methanol (Rivera et al., 2012).
contains one molecule of 2-((1H-benzimidazol-1-yl)methyl)phenol and half a molecule of benzene (Fig. 1). The solvent molecule subtends a dihedral angle of 78.90 (6)° with respect to the phenol substituent and 70.99 (6)° with respect to the benzimidazole moiety, which suggest an edge-to-face (T-shaped) C—H···An intermolecular hydrogen bond was observed in the crystal packing (Fig. 2) between the hydroxyl group of one molecule and a nitrogen atom of another one (Table 1). The O—H distance is longer than in (1H-benzimidazol-1-yl)methanol [0.894 (19)Å] (Rivera et al., 2012). However, the O···N distance [2.7200 (16)Å and 2.7355 (16)Å] and the O—H···N angle [174 (2)°, 173.8 (17)°] are similar in both structures. The O—H···N hydrogen bond connects the molecules forming chains running along the a-axis. The benzene molecule is linked to molecules of 2-((1H-benzimidazol-1-yl)methyl)phenol via C—H···π interactions (Fig. 3) acting as both a donor and an acceptor, Table 1. The benzimidazole moiety also forms two C—H···π interactions to the phenol rings of neighbouring molecules. These values are is similar to the values reported for other C—H···π interactions (Malathy Sony et al. 2005).
For related structures, see: Cai et al. (2006); Rivera et al. (2012); Shi et al. (2011). For another synthesis procedure, see: Milata et al. (2001); Rivera et al. (2008). For the pharmacological use of benzimidazoles, see: Alamgir et al. (2007). For C—H···π interactions, see: Malathy Sony & Ponnuswamy (2005).
A mixture of phenol (0.282 g, 3.00 mmol) and N1,N2-bis((1H-benzotriazol-1-yl)methyl)benzene-1,2-diamine (0.370 g, 1.00 mmol) was heated to 160 °C, after 5 minutes the mixture was cooled at room temperature until a sticky residue appeared. The product was purified by
using a mixture of benzene: ethyl acetate (80:20) as the mobile phase (yield 25 %, m.p.= 489-490 K). Single crystals were grown from a benzene:ethyl acetate solution by slow evaporation of the solvent at room temperature over a period of about one week. detailsAll H atoms were located in a difference map. The hydroxyl H atom was freely refined. H atoms bonded to C atoms were refined using a riding model, with secondary C—H = 0.99 Å and aromatic C—H = 0.95 Å and with Uiso(H) = 1.2Ueq(C).
Data collection: X-AREA (Stoe & Cie, 2001); cell
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: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C14H12N2O·0.5C6H6 | Z = 2 |
Mr = 263.31 | F(000) = 278 |
Triclinic, P1 | Dx = 1.290 Mg m−3 |
a = 8.9351 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3268 (10) Å | Cell parameters from 14234 reflections |
c = 9.9579 (11) Å | θ = 3.6–26.3° |
α = 73.098 (8)° | µ = 0.08 mm−1 |
β = 69.124 (8)° | T = 173 K |
γ = 62.148 (8)° | Needle, light brown |
V = 677.75 (15) Å3 | 0.42 × 0.12 × 0.12 mm |
Stoe IPDS II two-circle diffractometer | 2314 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.043 |
ω scans | θmax = 25.9°, θmin = 3.9° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −10→10 |
Tmin = 0.967, Tmax = 0.990 | k = −11→11 |
8981 measured reflections | l = −12→12 |
2591 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.039P)2 + 0.238P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
2591 reflections | Δρmax = 0.20 e Å−3 |
185 parameters | Δρmin = −0.17 e Å−3 |
C14H12N2O·0.5C6H6 | γ = 62.148 (8)° |
Mr = 263.31 | V = 677.75 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9351 (11) Å | Mo Kα radiation |
b = 9.3268 (10) Å | µ = 0.08 mm−1 |
c = 9.9579 (11) Å | T = 173 K |
α = 73.098 (8)° | 0.42 × 0.12 × 0.12 mm |
β = 69.124 (8)° |
Stoe IPDS II two-circle diffractometer | 2591 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 2314 reflections with I > 2σ(I) |
Tmin = 0.967, Tmax = 0.990 | Rint = 0.043 |
8981 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.20 e Å−3 |
2591 reflections | Δρmin = −0.17 e Å−3 |
185 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.26163 (13) | 0.72436 (14) | 0.00166 (12) | 0.0358 (3) | |
H1 | 0.155 (3) | 0.706 (3) | 0.023 (2) | 0.064 (6)* | |
N1 | 0.72313 (15) | 0.66159 (14) | 0.07264 (13) | 0.0272 (3) | |
N2 | 0.96889 (15) | 0.66557 (15) | 0.07838 (14) | 0.0323 (3) | |
C1 | 0.84911 (18) | 0.71998 (18) | 0.00788 (16) | 0.0298 (3) | |
H1A | 0.8506 | 0.7939 | −0.0809 | 0.036* | |
C2 | 0.91796 (18) | 0.56313 (17) | 0.20031 (15) | 0.0286 (3) | |
C3 | 0.76391 (18) | 0.55998 (16) | 0.19817 (15) | 0.0274 (3) | |
C4 | 0.6810 (2) | 0.46847 (19) | 0.30695 (17) | 0.0383 (4) | |
H4 | 0.5766 | 0.4670 | 0.3040 | 0.046* | |
C5 | 0.7585 (3) | 0.3802 (2) | 0.41906 (19) | 0.0478 (4) | |
H5 | 0.7057 | 0.3167 | 0.4963 | 0.057* | |
C6 | 0.9130 (3) | 0.3812 (2) | 0.42267 (18) | 0.0487 (5) | |
H6 | 0.9627 | 0.3176 | 0.5018 | 0.058* | |
C7 | 0.9953 (2) | 0.47195 (19) | 0.31466 (18) | 0.0397 (4) | |
H7 | 1.1000 | 0.4723 | 0.3180 | 0.048* | |
C8 | 0.57443 (18) | 0.69824 (19) | 0.02012 (16) | 0.0313 (3) | |
H8A | 0.5715 | 0.5940 | 0.0184 | 0.038* | |
H8B | 0.5908 | 0.7566 | −0.0808 | 0.038* | |
C11 | 0.40093 (17) | 0.80188 (16) | 0.11250 (15) | 0.0270 (3) | |
C12 | 0.24639 (18) | 0.80968 (17) | 0.09924 (15) | 0.0274 (3) | |
C13 | 0.08497 (18) | 0.90253 (18) | 0.18424 (16) | 0.0322 (3) | |
H13 | −0.0200 | 0.9101 | 0.1733 | 0.039* | |
C14 | 0.0764 (2) | 0.98409 (18) | 0.28484 (16) | 0.0341 (3) | |
H14 | −0.0341 | 1.0448 | 0.3444 | 0.041* | |
C15 | 0.2284 (2) | 0.97727 (18) | 0.29875 (16) | 0.0344 (3) | |
H15 | 0.2228 | 1.0335 | 0.3673 | 0.041* | |
C16 | 0.38896 (19) | 0.88763 (17) | 0.21170 (16) | 0.0309 (3) | |
H16 | 0.4930 | 0.8848 | 0.2201 | 0.037* | |
C21 | 0.4166 (2) | 0.9279 (2) | 0.62694 (19) | 0.0456 (4) | |
H21 | 0.3596 | 0.8781 | 0.7143 | 0.055* | |
C22 | 0.6494 (2) | 0.9049 (2) | 0.4094 (2) | 0.0455 (4) | |
H22 | 0.7529 | 0.8387 | 0.3470 | 0.055* | |
C23 | 0.5668 (2) | 0.8322 (2) | 0.5354 (2) | 0.0474 (4) | |
H23 | 0.6131 | 0.7161 | 0.5595 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0247 (5) | 0.0495 (7) | 0.0431 (6) | −0.0190 (5) | −0.0056 (4) | −0.0181 (5) |
N1 | 0.0209 (6) | 0.0305 (6) | 0.0328 (6) | −0.0121 (5) | −0.0084 (5) | −0.0038 (5) |
N2 | 0.0243 (6) | 0.0380 (7) | 0.0398 (7) | −0.0148 (5) | −0.0091 (5) | −0.0084 (5) |
C1 | 0.0265 (7) | 0.0340 (7) | 0.0320 (7) | −0.0160 (6) | −0.0075 (6) | −0.0030 (6) |
C2 | 0.0255 (7) | 0.0274 (7) | 0.0331 (7) | −0.0072 (5) | −0.0087 (6) | −0.0098 (6) |
C3 | 0.0246 (7) | 0.0246 (6) | 0.0308 (7) | −0.0073 (5) | −0.0062 (5) | −0.0073 (5) |
C4 | 0.0357 (8) | 0.0307 (8) | 0.0422 (9) | −0.0149 (6) | −0.0026 (7) | −0.0040 (6) |
C5 | 0.0580 (11) | 0.0309 (8) | 0.0373 (9) | −0.0133 (8) | −0.0038 (8) | −0.0004 (7) |
C6 | 0.0630 (12) | 0.0327 (8) | 0.0364 (9) | −0.0019 (8) | −0.0219 (8) | −0.0050 (7) |
C7 | 0.0381 (8) | 0.0359 (8) | 0.0440 (9) | −0.0020 (7) | −0.0211 (7) | −0.0140 (7) |
C8 | 0.0233 (7) | 0.0378 (8) | 0.0387 (8) | −0.0126 (6) | −0.0106 (6) | −0.0102 (6) |
C11 | 0.0241 (7) | 0.0272 (7) | 0.0318 (7) | −0.0117 (5) | −0.0099 (5) | −0.0018 (5) |
C12 | 0.0266 (7) | 0.0298 (7) | 0.0295 (7) | −0.0147 (6) | −0.0075 (5) | −0.0036 (5) |
C13 | 0.0238 (7) | 0.0357 (8) | 0.0383 (8) | −0.0156 (6) | −0.0055 (6) | −0.0044 (6) |
C14 | 0.0313 (8) | 0.0318 (7) | 0.0327 (8) | −0.0119 (6) | −0.0023 (6) | −0.0052 (6) |
C15 | 0.0418 (8) | 0.0294 (7) | 0.0320 (7) | −0.0116 (6) | −0.0137 (6) | −0.0046 (6) |
C16 | 0.0308 (7) | 0.0294 (7) | 0.0373 (8) | −0.0120 (6) | −0.0162 (6) | −0.0030 (6) |
C21 | 0.0432 (9) | 0.0642 (11) | 0.0411 (9) | −0.0337 (9) | −0.0094 (7) | −0.0055 (8) |
C22 | 0.0305 (8) | 0.0586 (11) | 0.0556 (10) | −0.0191 (8) | −0.0015 (7) | −0.0303 (9) |
C23 | 0.0391 (9) | 0.0384 (9) | 0.0715 (12) | −0.0159 (7) | −0.0207 (8) | −0.0098 (8) |
O1—C12 | 1.3602 (17) | C8—H8A | 0.9900 |
O1—H1 | 0.98 (2) | C8—H8B | 0.9900 |
N1—C1 | 1.3531 (18) | C11—C16 | 1.390 (2) |
N1—C3 | 1.3807 (19) | C11—C12 | 1.3999 (19) |
N1—C8 | 1.4570 (17) | C12—C13 | 1.391 (2) |
N2—C1 | 1.3101 (19) | C13—C14 | 1.386 (2) |
N2—C2 | 1.390 (2) | C13—H13 | 0.9500 |
C1—H1A | 0.9500 | C14—C15 | 1.385 (2) |
C2—C7 | 1.395 (2) | C14—H14 | 0.9500 |
C2—C3 | 1.398 (2) | C15—C16 | 1.387 (2) |
C3—C4 | 1.390 (2) | C15—H15 | 0.9500 |
C4—C5 | 1.374 (3) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C21—C22i | 1.370 (3) |
C5—C6 | 1.398 (3) | C21—C23 | 1.383 (3) |
C5—H5 | 0.9500 | C21—H21 | 0.9500 |
C6—C7 | 1.379 (3) | C22—C21i | 1.370 (3) |
C6—H6 | 0.9500 | C22—C23 | 1.375 (3) |
C7—H7 | 0.9500 | C22—H22 | 0.9500 |
C8—C11 | 1.5114 (19) | C23—H23 | 0.9500 |
C12—O1—H1 | 111.1 (12) | C11—C8—H8B | 109.0 |
C1—N1—C3 | 106.30 (12) | H8A—C8—H8B | 107.8 |
C1—N1—C8 | 126.83 (12) | C16—C11—C12 | 118.72 (13) |
C3—N1—C8 | 126.86 (12) | C16—C11—C8 | 122.58 (12) |
C1—N2—C2 | 104.48 (11) | C12—C11—C8 | 118.69 (12) |
N2—C1—N1 | 114.07 (13) | O1—C12—C13 | 122.49 (12) |
N2—C1—H1A | 123.0 | O1—C12—C11 | 117.60 (12) |
N1—C1—H1A | 123.0 | C13—C12—C11 | 119.91 (13) |
N2—C2—C7 | 130.19 (14) | C14—C13—C12 | 120.37 (13) |
N2—C2—C3 | 109.62 (12) | C14—C13—H13 | 119.8 |
C7—C2—C3 | 120.19 (14) | C12—C13—H13 | 119.8 |
N1—C3—C4 | 131.74 (14) | C15—C14—C13 | 120.17 (13) |
N1—C3—C2 | 105.52 (12) | C15—C14—H14 | 119.9 |
C4—C3—C2 | 122.74 (14) | C13—C14—H14 | 119.9 |
C5—C4—C3 | 116.22 (16) | C14—C15—C16 | 119.39 (13) |
C5—C4—H4 | 121.9 | C14—C15—H15 | 120.3 |
C3—C4—H4 | 121.9 | C16—C15—H15 | 120.3 |
C4—C5—C6 | 121.83 (16) | C15—C16—C11 | 121.41 (13) |
C4—C5—H5 | 119.1 | C15—C16—H16 | 119.3 |
C6—C5—H5 | 119.1 | C11—C16—H16 | 119.3 |
C7—C6—C5 | 121.91 (15) | C22i—C21—C23 | 119.45 (16) |
C7—C6—H6 | 119.0 | C22i—C21—H21 | 120.3 |
C5—C6—H6 | 119.0 | C23—C21—H21 | 120.3 |
C6—C7—C2 | 117.10 (16) | C21i—C22—C23 | 120.50 (16) |
C6—C7—H7 | 121.4 | C21i—C22—H22 | 119.8 |
C2—C7—H7 | 121.4 | C23—C22—H22 | 119.8 |
N1—C8—C11 | 112.97 (11) | C22—C23—C21 | 120.05 (17) |
N1—C8—H8A | 109.0 | C22—C23—H23 | 120.0 |
C11—C8—H8A | 109.0 | C21—C23—H23 | 120.0 |
N1—C8—H8B | 109.0 | ||
C2—N2—C1—N1 | −0.25 (16) | C3—C2—C7—C6 | −0.1 (2) |
C3—N1—C1—N2 | 0.43 (16) | C1—N1—C8—C11 | −110.59 (16) |
C8—N1—C1—N2 | −179.40 (12) | C3—N1—C8—C11 | 69.62 (17) |
C1—N2—C2—C7 | −179.68 (15) | N1—C8—C11—C16 | 15.8 (2) |
C1—N2—C2—C3 | −0.02 (15) | N1—C8—C11—C12 | −163.13 (12) |
C1—N1—C3—C4 | 179.49 (15) | C16—C11—C12—O1 | −179.84 (12) |
C8—N1—C3—C4 | −0.7 (2) | C8—C11—C12—O1 | −0.84 (19) |
C1—N1—C3—C2 | −0.40 (14) | C16—C11—C12—C13 | 0.2 (2) |
C8—N1—C3—C2 | 179.42 (12) | C8—C11—C12—C13 | 179.21 (13) |
N2—C2—C3—N1 | 0.27 (15) | O1—C12—C13—C14 | 178.38 (13) |
C7—C2—C3—N1 | 179.96 (12) | C11—C12—C13—C14 | −1.7 (2) |
N2—C2—C3—C4 | −179.63 (12) | C12—C13—C14—C15 | 1.7 (2) |
C7—C2—C3—C4 | 0.1 (2) | C13—C14—C15—C16 | −0.3 (2) |
N1—C3—C4—C5 | −179.58 (14) | C14—C15—C16—C11 | −1.2 (2) |
C2—C3—C4—C5 | 0.3 (2) | C12—C11—C16—C15 | 1.2 (2) |
C3—C4—C5—C6 | −0.6 (2) | C8—C11—C16—C15 | −177.73 (13) |
C4—C5—C6—C7 | 0.6 (3) | C21i—C22—C23—C21 | −0.3 (3) |
C5—C6—C7—C2 | −0.2 (2) | C22i—C21—C23—C22 | 0.3 (3) |
N2—C2—C7—C6 | 179.51 (14) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C2–C7, N1/N2/C1–C3, C21–C23/C21'–C23' and C11–C16 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2ii | 0.98 (2) | 1.74 (2) | 2.7200 (16) | 174 (2) |
C22—H22···Cg1 | 0.95 | 3.25 | 3.868 | 124 |
C22—H22···Cg2 | 0.95 | 3.10 | 3.844 | 137 |
C15—H15···Cg3 | 0.95 | 3.06 | 3.761 | 132 |
C16—H16···Cg3 | 0.95 | 3.30 | 3.883 | 122 |
C1—H1A···Cg4iii | 0.95 | 2.65 | 3.467 | 145 |
C5—H5···Cg4iv | 0.95 | 3.17 | 3.922 | 138 |
Symmetry codes: (ii) x−1, y, z; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+1, −z+1. |
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C2–C7, N1/N2/C1–C3, C21–C23/C21'–C23' and C11–C16 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.98 (2) | 1.74 (2) | 2.7200 (16) | 174 (2) |
C22—H22···Cg1 | 0.95 | 3.25 | 3.868 | 124 |
C22—H22···Cg2 | 0.95 | 3.10 | 3.844 | 137 |
C15—H15···Cg3 | 0.95 | 3.06 | 3.761 | 132 |
C16—H16···Cg3 | 0.95 | 3.30 | 3.883 | 122 |
C1—H1A···Cg4ii | 0.95 | 2.65 | 3.467 | 145 |
C5—H5···Cg4iii | 0.95 | 3.17 | 3.922 | 138 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z+1. |
Acknowledgements
We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work. LJ-C acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.
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