Literature DB >> 22346939

1,1'-[(2-Phenyl-2,3-dihydro-1H-benz-imidazole-1,3-di-yl)bis-(methyl-ene)]bis-(1H-benzotriazole).

Augusto Rivera, Hector Jairo Osorio, Jaime Ríos-Motta, Karla Fejfarová, Michal Dušek.   

Abstract

The imidazole ring in the title compound, C(27)H(22)N(8), adopts a slight envelope conformation with the C atom carrying the phenyl ring being the flap atom. The phenyl ring is almost perpendicular to the mean plane of the imidazole ring [dihedral angle = 88.90 (7)°]. The (1H-benzotriazol-1-yl)methyl groups bound to the imidazole ring are positioned on the same side of the imidazole ring. The dihedral angle between these benzotriazolyl rings is 17.71 (5)°. The crystal packing is stabilized by a C-H⋯π inter-action, which connects the mol-ecules into zigzag chains running along the b axis.

Entities:  

Year:  2012        PMID： 22346939      PMCID： PMC3274994          DOI： 10.1107/S1600536811055486

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For a related structure see: Rivera et al. (2011 ▶). For the synthesis of the precursor and the title compound, see: Rivera et al. (2000 ▶, 2004 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C27H22N8 M = 458.5 Orthorhombic, a = 9.2721 (2) Å b = 13.6449 (3) Å c = 17.1883 (4) Å V = 2174.61 (8) Å3 Z = 4 Cu Kα radiation μ = 0.70 mm−1 T = 120 K 0.38 × 0.25 × 0.18 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.325, T max = 1 27948 measured reflections 2206 independent reflections 2149 reflections with I > 3σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 0.080 S = 1.80 2206 reflections 317 parameters H-atom parameters constrained Δρmax = 0.12 e Å−3 Δρmin = −0.12 e Å−3 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. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055486/bt5766sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055486/bt5766Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811055486/bt5766Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C27H22N8F(000) = 960
Mr = 458.5Dx = 1.400 Mg m−3
Orthorhombic, P212121Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2abCell parameters from 20891 reflections
a = 9.2721 (2) Åθ = 3.2–67.0°
b = 13.6449 (3) ŵ = 0.70 mm−1
c = 17.1883 (4) ÅT = 120 K
V = 2174.61 (8) Å3Prism, colourless
Z = 40.38 × 0.25 × 0.18 mm
Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector2206 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source2149 reflections with I > 3σ(I)
mirrorRint = 0.030
Detector resolution: 10.3784 pixels mm-1θmax = 67.1°, θmin = 4.1°
Rotation method data acquisition using ω scansh = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)k = −16→16
Tmin = 0.325, Tmax = 1l = −19→17
27948 measured reflections
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
wR(F2) = 0.080(Δ/σ)max = 0.005
S = 1.80Δρmax = 0.12 e Å−3
2206 reflectionsΔρmin = −0.12 e Å−3
317 parametersExtinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraintsExtinction coefficient: 2500 (500)
88 constraints
Experimental. CrysAlisPro (Agilent, 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.
xyzUiso*/Ueq
N1−0.07910 (16)−0.13039 (11)0.82518 (8)0.0261 (4)
N20.05744 (16)−0.14326 (11)0.83819 (8)0.0247 (4)
N30.13057 (15)−0.13457 (9)0.76964 (8)0.0195 (4)
N40.37643 (15)−0.06878 (9)0.78252 (8)0.0189 (4)
N50.40183 (15)0.08309 (9)0.83954 (8)0.0191 (4)
N60.20270 (16)0.15999 (10)0.90914 (8)0.0206 (4)
N70.16374 (17)0.16645 (11)0.98552 (9)0.0267 (5)
N80.02387 (18)0.16322 (11)0.99042 (9)0.0293 (5)
C10.03639 (18)−0.11614 (10)0.71046 (10)0.0190 (4)
C2−0.0979 (2)−0.11366 (11)0.74674 (10)0.0211 (5)
C3−0.2245 (2)−0.09657 (11)0.70390 (10)0.0234 (5)
C4−0.2101 (2)−0.08297 (12)0.62504 (10)0.0253 (5)
C5−0.07273 (19)−0.08592 (12)0.58905 (11)0.0251 (5)
C60.0524 (2)−0.10235 (12)0.62995 (10)0.0227 (5)
C70.28645 (18)−0.15303 (11)0.76888 (9)0.0199 (4)
C80.35676 (18)−0.01825 (11)0.85796 (9)0.0179 (4)
C90.39816 (17)0.00203 (11)0.72380 (10)0.0195 (4)
C100.41143 (17)0.09406 (11)0.75863 (10)0.0192 (4)
C110.43808 (18)0.17649 (12)0.71390 (10)0.0246 (5)
C120.45606 (18)0.16400 (13)0.63336 (11)0.0282 (5)
C130.44790 (19)0.07213 (14)0.59973 (11)0.0274 (5)
C140.41670 (17)−0.01080 (13)0.64492 (10)0.0228 (5)
C150.44554 (18)−0.06662 (11)0.92129 (9)0.0185 (4)
C160.59542 (19)−0.07058 (11)0.91582 (10)0.0211 (5)
C170.6749 (2)−0.11935 (13)0.97213 (10)0.0248 (5)
C180.6050 (2)−0.16512 (12)1.03365 (10)0.0259 (5)
C190.4558 (2)−0.16208 (13)1.03928 (10)0.0272 (5)
C200.3761 (2)−0.11246 (12)0.98311 (10)0.0238 (5)
C210.35731 (18)0.16107 (11)0.89023 (10)0.0217 (5)
C220.08283 (18)0.15079 (11)0.86383 (10)0.0196 (4)
C23−0.0315 (2)0.15290 (11)0.91632 (10)0.0234 (5)
C24−0.1745 (2)0.14330 (13)0.89103 (11)0.0275 (5)
C25−0.19652 (19)0.13049 (12)0.81287 (11)0.0269 (5)
C26−0.0803 (2)0.12856 (11)0.75995 (10)0.0241 (5)
C270.06078 (18)0.13921 (11)0.78313 (10)0.0207 (4)
H3−0.317263−0.0944840.7286940.0281*
H4−0.294358−0.0713010.5939080.0303*
H5−0.066743−0.0760540.5338490.0301*
H60.144966−0.1042740.6050050.0273*
H7a0.309239−0.2031890.806070.0239*
H7b0.312986−0.1830380.7204370.0239*
H80.260422−0.0205740.8783410.0215*
H110.444080.2402790.7372350.0295*
H120.4743030.2201370.6011730.0339*
H130.4637730.0650140.5448280.0328*
H140.408525−0.0744980.6216190.0273*
H160.643668−0.0394980.8730040.0254*
H170.778212−0.1214750.9685960.0297*
H180.660142−0.1990461.0724810.0311*
H190.407706−0.194071.0817370.0327*
H200.272852−0.1098490.987030.0285*
H21a0.3821040.2229430.8672540.026*
H21b0.4125790.1586130.9374150.026*
H24−0.2536940.1456050.9269640.0329*
H25−0.2930960.1226680.793720.0323*
H26−0.1004480.1194520.705650.0289*
H270.1392830.1387880.7467180.0248*
U11U22U33U12U13U23
N10.0243 (8)0.0316 (7)0.0223 (7)−0.0027 (6)0.0026 (6)0.0007 (6)
N20.0248 (8)0.0270 (7)0.0224 (7)−0.0032 (6)0.0002 (6)0.0027 (6)
N30.0199 (7)0.0200 (6)0.0186 (7)−0.0020 (6)0.0001 (5)0.0009 (5)
N40.0206 (7)0.0187 (6)0.0173 (7)−0.0004 (5)−0.0010 (6)0.0001 (5)
N50.0205 (7)0.0163 (6)0.0203 (7)0.0005 (5)−0.0014 (5)−0.0007 (5)
N60.0235 (7)0.0204 (6)0.0178 (7)0.0026 (5)−0.0010 (6)−0.0020 (5)
N70.0334 (9)0.0276 (7)0.0192 (7)0.0056 (6)0.0003 (6)−0.0024 (6)
N80.0333 (9)0.0311 (7)0.0236 (8)0.0049 (6)0.0041 (6)0.0020 (6)
C10.0212 (8)0.0136 (6)0.0224 (8)−0.0009 (6)−0.0026 (7)−0.0005 (6)
C20.0228 (9)0.0170 (7)0.0234 (8)−0.0018 (6)0.0003 (7)−0.0004 (6)
C30.0198 (8)0.0211 (7)0.0295 (9)−0.0005 (6)0.0009 (7)−0.0011 (6)
C40.0252 (9)0.0223 (8)0.0283 (9)0.0014 (7)−0.0043 (7)0.0013 (7)
C50.0262 (10)0.0260 (8)0.0231 (9)0.0004 (7)−0.0014 (7)0.0018 (7)
C60.0237 (9)0.0219 (7)0.0227 (9)0.0000 (6)0.0014 (7)0.0000 (6)
C70.0194 (8)0.0164 (7)0.0238 (8)−0.0003 (6)−0.0029 (6)−0.0006 (6)
C80.0173 (8)0.0181 (7)0.0184 (8)−0.0003 (6)0.0009 (6)−0.0001 (6)
C90.0138 (7)0.0228 (7)0.0219 (8)0.0008 (6)−0.0004 (6)0.0034 (6)
C100.0139 (8)0.0224 (7)0.0214 (8)0.0009 (6)−0.0010 (6)0.0018 (6)
C110.0205 (8)0.0224 (7)0.0308 (9)−0.0013 (6)−0.0019 (7)0.0059 (7)
C120.0205 (9)0.0334 (9)0.0309 (10)−0.0033 (7)−0.0016 (7)0.0129 (7)
C130.0192 (9)0.0414 (9)0.0215 (9)0.0009 (7)0.0000 (7)0.0062 (7)
C140.0175 (8)0.0306 (8)0.0202 (8)0.0016 (7)−0.0008 (6)0.0007 (7)
C150.0237 (8)0.0162 (7)0.0157 (8)0.0006 (6)−0.0007 (6)−0.0013 (6)
C160.0240 (9)0.0207 (7)0.0188 (8)−0.0019 (6)0.0023 (7)0.0000 (6)
C170.0234 (9)0.0271 (8)0.0238 (9)0.0027 (6)−0.0037 (7)−0.0041 (7)
C180.0354 (10)0.0241 (7)0.0183 (8)0.0046 (7)−0.0045 (7)0.0007 (6)
C190.0358 (10)0.0257 (8)0.0202 (8)−0.0025 (7)0.0033 (7)0.0032 (7)
C200.0232 (9)0.0250 (8)0.0231 (9)−0.0011 (7)0.0033 (7)−0.0005 (6)
C210.0211 (8)0.0197 (7)0.0241 (8)0.0000 (6)−0.0030 (7)−0.0037 (6)
C220.0208 (8)0.0149 (6)0.0230 (8)0.0020 (6)−0.0009 (7)0.0014 (6)
C230.0285 (9)0.0180 (7)0.0236 (8)0.0034 (6)0.0033 (7)0.0028 (6)
C240.0233 (9)0.0228 (8)0.0362 (10)0.0025 (7)0.0078 (7)0.0054 (7)
C250.0213 (9)0.0203 (7)0.0392 (11)0.0000 (7)−0.0026 (7)0.0057 (7)
C260.0263 (9)0.0187 (7)0.0273 (9)0.0013 (7)−0.0039 (7)0.0009 (6)
C270.0213 (8)0.0195 (7)0.0212 (8)0.0018 (6)0.0003 (7)−0.0002 (6)
N1—N21.298 (2)C10—C111.385 (2)
N1—C21.379 (2)C11—C121.405 (3)
N2—N31.365 (2)C11—H110.96
N3—C11.364 (2)C12—C131.382 (3)
N3—C71.467 (2)C12—H120.96
N4—C71.440 (2)C13—C141.403 (3)
N4—C81.480 (2)C13—H130.96
N4—C91.412 (2)C14—H140.96
N5—C81.479 (2)C15—C161.394 (2)
N5—C101.402 (2)C15—C201.391 (2)
N5—C211.436 (2)C16—C171.387 (2)
N6—N71.364 (2)C16—H160.96
N6—C211.470 (2)C17—C181.389 (2)
N6—C221.363 (2)C17—H170.96
N7—N81.300 (2)C18—C191.387 (3)
N8—C231.380 (2)C18—H180.96
C1—C21.393 (2)C19—C201.392 (2)
C1—C61.404 (2)C19—H190.96
C2—C31.405 (3)C20—H200.96
C3—C41.375 (3)C21—H21a0.96
C3—H30.96C21—H21b0.96
C4—C51.417 (3)C22—C231.392 (2)
C4—H40.96C22—C271.411 (2)
C5—C61.375 (3)C23—C241.402 (3)
C5—H50.96C24—C251.370 (3)
C6—H60.96C24—H240.96
C7—H7a0.96C25—C261.411 (3)
C7—H7b0.96C25—H250.96
C8—C151.516 (2)C26—C271.375 (2)
C8—H80.96C26—H260.96
C9—C101.397 (2)C27—H270.96
C9—C141.378 (2)
N2—N1—C2108.32 (14)C10—C11—H11120.9899
N1—N2—N3108.92 (13)C12—C11—H11120.9894
N2—N3—C1109.99 (14)C11—C12—C13121.04 (17)
N2—N3—C7118.83 (13)C11—C12—H12119.4794
C1—N3—C7130.98 (14)C13—C12—H12119.4802
C7—N4—C8116.31 (13)C12—C13—C14120.74 (17)
C7—N4—C9120.85 (13)C12—C13—H13119.6288
C8—N4—C9108.98 (12)C14—C13—H13119.6289
C8—N5—C10109.28 (12)C9—C14—C13117.92 (16)
C8—N5—C21118.80 (13)C9—C14—H14121.0407
C10—N5—C21122.76 (13)C13—C14—H14121.0413
N7—N6—C21118.06 (14)C8—C15—C16120.64 (14)
N7—N6—C22109.87 (14)C8—C15—C20119.52 (15)
C21—N6—C22132.05 (14)C16—C15—C20119.73 (15)
N6—N7—N8108.92 (14)C15—C16—C17120.10 (15)
N7—N8—C23108.32 (15)C15—C16—H16119.9515
N3—C1—C2104.06 (14)C17—C16—H16119.9514
N3—C1—C6133.79 (16)C16—C17—C18119.92 (17)
C2—C1—C6122.15 (16)C16—C17—H17120.0389
N1—C2—C1108.71 (15)C18—C17—H17120.0394
N1—C2—C3130.20 (16)C17—C18—C19120.36 (16)
C1—C2—C3121.09 (15)C17—C18—H18119.8197
C2—C3—C4117.25 (16)C19—C18—H18119.819
C2—C3—H3121.3774C18—C19—C20119.71 (16)
C4—C3—H3121.3773C18—C19—H19120.1465
C3—C4—C5120.93 (17)C20—C19—H19120.1462
C3—C4—H4119.5339C15—C20—C19120.18 (17)
C5—C4—H4119.5344C15—C20—H20119.9089
C4—C5—C6122.70 (17)C19—C20—H20119.9072
C4—C5—H5118.6524N5—C21—N6114.03 (13)
C6—C5—H5118.6526N5—C21—H21a109.4706
C1—C6—C5115.89 (16)N5—C21—H21b109.4714
C1—C6—H6122.0553N6—C21—H21a109.4709
C5—C6—H6122.0541N6—C21—H21b109.4714
N3—C7—N4115.62 (12)H21a—C21—H21b104.4982
N3—C7—H7a109.4709N6—C22—C23104.40 (14)
N3—C7—H7b109.471N6—C22—C27133.65 (16)
N4—C7—H7a109.4713C23—C22—C27121.94 (16)
N4—C7—H7b109.4716N8—C23—C22108.49 (16)
H7a—C7—H7b102.5346N8—C23—C24130.34 (17)
N4—C8—N5102.31 (12)C22—C23—C24121.16 (16)
N4—C8—C15111.06 (12)C23—C24—C25117.19 (17)
N4—C8—H8114.7756C23—C24—H24121.4053
N5—C8—C15114.04 (13)C25—C24—H24121.4053
N5—C8—H8111.8387C24—C25—C26121.39 (17)
C15—C8—H8103.2226C24—C25—H25119.3049
N4—C9—C10108.75 (14)C26—C25—H25119.3045
N4—C9—C14129.38 (15)C25—C26—C27122.55 (16)
C10—C9—C14121.67 (15)C25—C26—H26118.7268
N5—C10—C9108.88 (13)C27—C26—H26118.7256
N5—C10—C11130.47 (15)C22—C27—C26115.76 (15)
C9—C10—C11120.54 (15)C22—C27—H27122.1215
C10—C11—C12118.02 (16)C26—C27—H27122.1225
?—?—?—??
Cg6 is the centroid of the C15–C20 aromatic ring.
D—H···AD—HH···AD···AD—H···A
C12—H12···Cg6i0.962.613.5597 (19)169
Table 1

Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of the C15–C20 aromatic ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C12—H12⋯Cg6i0.962.613.5597 (19)169

Symmetry code: (i) .

  1 in total

1.  1,3-Bis[(1H-benzotriazol-1-yl)meth-yl]-2,3-dihydro-1H-benzimidazole.

Authors:  Augusto Rivera; Mauricio Maldonado; José Luis Casas; Michal Dušek; Karla Fejfarová
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-03-26
  1 in total

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