Literature DB >> 21580039

2-Phenyl-4,5-di-2-pyridyl-1H-imidazole.

Marika Felsmann1, Diana Schindler, Edwin Weber.   

Abstract

In the title compound, C(19)H(14)N(4), which was crystallized from dimethyl sulfoxide, the arene and heterocyclic rings of the lophine analogue framework differ only slightly from coplanarity (dihedral angles range from 8.8 to 20.2°), and intramolecular N-H⋯N and C-H⋯N interactions help to establish the conformation. The crystal packing features a number of weak C-H⋯N, N-H⋯N hydrogen-bond type contacts, and C-H⋯π interactions, leading to the formation of a herringbone structure.

Entities:  

Year:  2009        PMID： 21580039      PMCID： PMC2980126          DOI： 10.1107/S1600536809053215

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


Related literature

For the solid-state structures of 2,4,5-triphenyl­imidazoles, see: Kaftory et al. (1998 ▶); Benisvy et al. (2003 ▶); Martinez et al. (2004 ▶); Seethalakshmi et al. (2006 ▶); Thiruvalluvar et al. (2007 ▶). For the synthesis of the title compound, see: Nakashima et al. (1998 ▶); Slater et al. (2006 ▶). For weak hydrogen-bond type contacts, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C19H14N4 M = 298.34 Monoclinic, a = 8.7394 (3) Å b = 15.3333 (5) Å c = 11.2980 (4) Å β = 106.835 (2)° V = 1449.09 (9) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 153 K 0.32 × 0.20 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.974, T max = 0.993 14338 measured reflections 2562 independent reflections 2130 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.084 S = 1.04 2562 reflections 212 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.19 e Å−3 Δρmin = −0.19 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053215/im2166sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053215/im2166Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H14N4F(000) = 624
Mr = 298.34Dx = 1.368 Mg m−3
Monoclinic, P21/nMelting point: 462 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 8.7394 (3) ÅCell parameters from 4480 reflections
b = 15.3333 (5) Åθ = 2.3–28.9°
c = 11.2980 (4) ŵ = 0.08 mm−1
β = 106.835 (2)°T = 153 K
V = 1449.09 (9) Å3Plate, colourless
Z = 40.32 × 0.20 × 0.08 mm
Bruker SMART CCD area-detector diffractometer2562 independent reflections
Radiation source: fine-focus sealed tube2130 reflections with I > 2σ(I)
graphiteRint = 0.029
phi and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −10→10
Tmin = 0.974, Tmax = 0.993k = −17→18
14338 measured reflectionsl = −12→13
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0408P)2 + 0.3271P] where P = (Fo2 + 2Fc2)/3
2562 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/UeqOcc. (<1)
N10.91201 (12)0.18912 (7)−0.10112 (9)0.0237 (3)
N20.86233 (11)0.09328 (7)0.02858 (9)0.0239 (3)
N31.16211 (13)0.28374 (8)−0.11585 (10)0.0331 (3)
N41.24782 (12)0.12084 (7)0.25734 (10)0.0265 (3)
C10.80100 (14)0.13607 (8)−0.07612 (11)0.0226 (3)
C21.02004 (14)0.11894 (8)0.07188 (11)0.0225 (3)
C31.05460 (14)0.17873 (8)−0.00916 (11)0.0224 (3)
C41.19531 (14)0.22527 (8)−0.02296 (11)0.0239 (3)
C51.35107 (14)0.20897 (9)0.04894 (12)0.0292 (3)
H51.37190.16720.11380.035*
C61.47484 (16)0.25437 (9)0.02471 (13)0.0333 (3)
H61.58200.24400.07270.040*
C71.44232 (17)0.31470 (10)−0.06921 (13)0.0352 (3)
H71.52560.3470−0.08710.042*
C81.28509 (18)0.32678 (10)−0.13653 (14)0.0386 (4)
H81.26250.3683−0.20180.046*
C91.11465 (14)0.08007 (8)0.19008 (11)0.0224 (3)
C101.06033 (15)0.00341 (9)0.23010 (11)0.0264 (3)
H100.9655−0.02380.18100.032*
C111.14491 (15)−0.03268 (9)0.34130 (12)0.0292 (3)
H111.1095−0.08510.36980.035*
C121.28242 (15)0.00858 (9)0.41110 (12)0.0295 (3)
H121.3430−0.01450.48850.035*
C131.32884 (15)0.08392 (9)0.36510 (12)0.0292 (3)
H131.42420.11160.41250.035*
C140.63692 (14)0.12433 (8)−0.15534 (11)0.0233 (3)
C150.56985 (15)0.17767 (9)−0.25665 (11)0.0267 (3)
H150.63200.2225−0.27820.032*
C160.41256 (15)0.16545 (9)−0.32612 (12)0.0318 (3)
H160.36720.2020−0.39530.038*
C170.32096 (15)0.10063 (10)−0.29574 (12)0.0329 (3)
H170.21260.0932−0.34310.040*
C180.38761 (15)0.04655 (9)−0.19604 (12)0.0322 (3)
H180.32520.0016−0.17520.039*
C190.54504 (15)0.05787 (9)−0.12681 (12)0.0286 (3)
H190.59080.0200−0.05930.034*
Cg10.93000.1432−0.01720.010*0.00
Cg21.31850.2690−0.04520.010*0.00
Cg30.47880.1121−0.22610.010*0.00
H10.9009 (17)0.2253 (10)−0.1644 (14)0.039 (4)*
Cg41.19650.04400.29920.010*0.00
U11U22U33U12U13U23
N10.0238 (5)0.0238 (6)0.0216 (5)−0.0007 (4)0.0034 (4)0.0019 (5)
N20.0211 (5)0.0254 (6)0.0235 (5)−0.0007 (4)0.0036 (4)−0.0004 (4)
N30.0323 (6)0.0319 (7)0.0354 (6)−0.0016 (5)0.0106 (5)0.0060 (5)
N40.0214 (5)0.0279 (7)0.0274 (5)0.0009 (4)0.0026 (4)0.0008 (5)
C10.0225 (6)0.0215 (7)0.0228 (6)0.0003 (5)0.0053 (5)−0.0014 (5)
C20.0202 (6)0.0224 (7)0.0240 (6)0.0007 (5)0.0052 (5)−0.0020 (5)
C30.0211 (6)0.0218 (7)0.0226 (6)0.0005 (5)0.0039 (5)−0.0031 (5)
C40.0255 (6)0.0216 (7)0.0255 (6)−0.0005 (5)0.0089 (5)−0.0045 (5)
C50.0253 (7)0.0313 (8)0.0315 (7)−0.0010 (6)0.0088 (5)−0.0011 (6)
C60.0247 (7)0.0388 (9)0.0376 (8)−0.0037 (6)0.0110 (6)−0.0072 (7)
C70.0343 (8)0.0358 (9)0.0415 (8)−0.0103 (6)0.0203 (6)−0.0076 (7)
C80.0424 (8)0.0361 (9)0.0408 (8)−0.0056 (7)0.0174 (7)0.0076 (7)
C90.0197 (6)0.0234 (7)0.0242 (6)0.0029 (5)0.0064 (5)−0.0022 (5)
C100.0235 (6)0.0260 (7)0.0283 (7)−0.0010 (5)0.0053 (5)−0.0011 (6)
C110.0302 (7)0.0264 (8)0.0317 (7)0.0006 (6)0.0101 (6)0.0045 (6)
C120.0284 (7)0.0310 (8)0.0264 (7)0.0066 (6)0.0035 (5)0.0040 (6)
C130.0229 (6)0.0319 (8)0.0285 (7)0.0018 (5)0.0006 (5)0.0001 (6)
C140.0226 (6)0.0242 (7)0.0226 (6)0.0015 (5)0.0055 (5)−0.0041 (5)
C150.0253 (7)0.0270 (8)0.0264 (7)−0.0005 (5)0.0053 (5)0.0006 (5)
C160.0279 (7)0.0373 (8)0.0261 (7)0.0040 (6)0.0012 (6)0.0028 (6)
C170.0225 (6)0.0428 (9)0.0294 (7)−0.0018 (6)0.0012 (5)−0.0031 (6)
C180.0274 (7)0.0359 (8)0.0324 (7)−0.0083 (6)0.0072 (6)−0.0015 (6)
C190.0275 (7)0.0305 (8)0.0257 (7)−0.0014 (6)0.0045 (5)0.0015 (6)
N1—Cg11.1544 (11)C7—H70.9500
N1—C11.3570 (16)C8—H80.9500
N1—C31.3813 (15)C9—C101.3913 (19)
N1—H10.888 (16)C10—C111.3759 (17)
N2—Cg11.1751 (11)C10—H100.9500
N2—C11.3228 (15)C11—C121.3846 (18)
N2—C21.3796 (15)C11—H110.9500
N3—C81.3382 (18)C12—C131.3753 (19)
N3—C41.3465 (16)C12—H120.9500
N4—C131.3435 (16)C13—H130.9500
N4—C91.3456 (15)C14—C151.3907 (17)
C1—Cg11.1364 (11)C14—C191.3919 (18)
C1—C141.4650 (16)C14—Cg31.3942 (12)
C2—Cg11.1454 (11)C15—C161.3841 (17)
C2—C31.3893 (18)C15—H150.9500
C2—C91.4774 (16)C16—C171.381 (2)
C3—Cg11.1972 (12)C16—H160.9500
C3—C41.4686 (17)C17—C181.3841 (19)
C4—Cg21.3514 (13)C17—H170.9500
C4—C51.3909 (17)C18—C191.3825 (17)
C5—C61.3788 (19)C18—H180.9500
C5—H50.9500C19—H190.9500
C6—C71.374 (2)Cg2—Cg3i3.6866
C6—H60.9500Cg3—Cg4ii3.9773
C7—C81.377 (2)
Cg1—N1—C153.07 (7)N4—C9—C10121.99 (11)
Cg1—N1—C355.48 (7)N4—C9—C2119.28 (11)
C1—N1—C3108.54 (10)C10—C9—C2118.70 (11)
Cg1—N1—H1178.2 (10)C11—C10—C9119.53 (11)
C1—N1—H1128.6 (9)C11—C10—H10120.2
C3—N1—H1122.9 (9)C9—C10—H10120.2
Cg1—N2—C153.73 (7)C10—C11—C12118.97 (13)
Cg1—N2—C252.54 (7)C10—C11—H11120.5
C1—N2—C2106.27 (10)C12—C11—H11120.5
C8—N3—C4117.50 (11)C13—C12—C11118.10 (12)
C13—N4—C9117.30 (11)C13—C12—H12121.0
Cg1—C1—N256.48 (7)C11—C12—H12121.0
Cg1—C1—N154.29 (7)N4—C13—C12124.11 (12)
N2—C1—N1110.76 (10)N4—C13—H13117.9
Cg1—C1—C14177.65 (13)C12—C13—H13117.9
N2—C1—C14123.84 (11)C15—C14—C19119.16 (11)
N1—C1—C14125.36 (11)C15—C14—Cg359.71 (7)
Cg1—C2—N254.52 (6)C19—C14—Cg359.46 (7)
Cg1—C2—C355.36 (7)C15—C14—C1122.36 (12)
N2—C2—C3109.88 (10)C19—C14—C1118.47 (11)
Cg1—C2—C9170.96 (12)Cg3—C14—C1177.47 (11)
N2—C2—C9116.46 (11)C16—C15—C14119.99 (13)
C3—C2—C9133.65 (11)C16—C15—H15120.0
Cg1—C3—N152.60 (7)C14—C15—H15120.0
Cg1—C3—C251.93 (7)C17—C16—C15120.57 (12)
N1—C3—C2104.53 (10)C17—C16—H16119.7
Cg1—C3—C4169.78 (11)C15—C16—H16119.7
N1—C3—C4117.70 (11)C16—C17—C18119.74 (12)
C2—C3—C4137.66 (11)C16—C17—H17120.1
N3—C4—Cg261.88 (7)C18—C17—H17120.1
N3—C4—C5121.89 (12)C19—C18—C17120.04 (13)
Cg2—C4—C560.02 (8)C19—C18—H18120.0
N3—C4—C3114.09 (11)C17—C18—H18120.0
Cg2—C4—C3175.49 (11)C18—C19—C14120.48 (12)
C5—C4—C3123.96 (12)C18—C19—H19119.8
C6—C5—C4118.99 (13)C14—C19—H19119.8
C6—C5—H5120.5C1—Cg1—C2142.73 (9)
C4—C5—H5120.5C1—Cg1—N172.65 (8)
C7—C6—C5119.64 (13)C2—Cg1—N1144.62 (8)
C7—C6—H6120.2C1—Cg1—N269.79 (8)
C5—C6—H6120.2C2—Cg1—N272.94 (8)
C6—C7—C8117.86 (13)N1—Cg1—N2142.43 (7)
C6—C7—H7121.1C1—Cg1—C3144.55 (9)
C8—C7—H7121.1C2—Cg1—C372.71 (8)
N3—C8—C7124.11 (14)N1—Cg1—C371.92 (8)
N3—C8—H8117.9N2—Cg1—C3145.65 (7)
C7—C8—H8117.9
C2—N2—C1—Cg1−0.20 (8)Cg1—C1—C14—C15−91 (3)
Cg1—N2—C1—N1−0.66 (8)N2—C1—C14—C15171.95 (12)
C2—N2—C1—N1−0.87 (14)N1—C1—C14—C15−10.5 (2)
Cg1—N2—C1—C14177.20 (15)Cg1—C1—C14—C1990 (3)
C2—N2—C1—C14176.99 (11)N2—C1—C14—C19−7.35 (19)
C3—N1—C1—Cg10.83 (8)N1—C1—C14—C19170.20 (12)
Cg1—N1—C1—N20.68 (8)Cg1—C1—C14—Cg3124 (3)
C3—N1—C1—N21.51 (14)N2—C1—C14—Cg327 (3)
Cg1—N1—C1—C14−177.14 (15)N1—C1—C14—Cg3−155 (3)
C3—N1—C1—C14−176.31 (12)C19—C14—C15—C161.3 (2)
C1—N2—C2—Cg10.21 (8)Cg3—C14—C15—C160.35 (11)
Cg1—N2—C2—C3−0.30 (8)C1—C14—C15—C16−177.96 (12)
C1—N2—C2—C3−0.09 (14)C14—C15—C16—C170.1 (2)
Cg1—N2—C2—C9179.24 (13)C15—C16—C17—C18−0.9 (2)
C1—N2—C2—C9179.44 (11)C16—C17—C18—C190.4 (2)
C1—N1—C3—Cg1−0.81 (8)C17—C18—C19—C141.0 (2)
Cg1—N1—C3—C2−0.66 (7)C15—C14—C19—C18−1.9 (2)
C1—N1—C3—C2−1.47 (13)Cg3—C14—C19—C18−0.90 (11)
Cg1—N1—C3—C4176.16 (13)C1—C14—C19—C18177.43 (12)
C1—N1—C3—C4175.36 (11)N2—C1—Cg1—C20.39 (16)
N2—C2—C3—Cg10.30 (8)N1—C1—Cg1—C2179.63 (13)
C9—C2—C3—Cg1−179.13 (17)C14—C1—Cg1—C2−98 (3)
Cg1—C2—C3—N10.67 (8)N2—C1—Cg1—N1−179.24 (9)
N2—C2—C3—N10.97 (14)C14—C1—Cg1—N182 (3)
C9—C2—C3—N1−178.46 (13)N1—C1—Cg1—N2179.24 (9)
Cg1—C2—C3—C4−175.16 (18)C14—C1—Cg1—N2−98 (3)
N2—C2—C3—C4−174.86 (14)N2—C1—Cg1—C3179.19 (13)
C9—C2—C3—C45.7 (3)N1—C1—Cg1—C3−1.57 (16)
C8—N3—C4—Cg2−0.24 (11)C14—C1—Cg1—C381 (3)
C8—N3—C4—C5−0.53 (19)N2—C2—Cg1—C1−0.38 (15)
C8—N3—C4—C3−177.97 (12)C3—C2—Cg1—C1179.27 (14)
Cg1—C3—C4—N327.1 (7)C9—C2—Cg1—C1−4.7 (8)
N1—C3—C4—N39.70 (16)N2—C2—Cg1—N1179.00 (13)
C2—C3—C4—N3−174.85 (14)C3—C2—Cg1—N1−1.34 (15)
Cg1—C3—C4—Cg21(2)C9—C2—Cg1—N1174.7 (7)
N1—C3—C4—Cg2−16.6 (15)C3—C2—Cg1—N2179.65 (9)
C2—C3—C4—Cg2158.8 (13)C9—C2—Cg1—N2−4.4 (7)
Cg1—C3—C4—C5−150.2 (6)N2—C2—Cg1—C3−179.65 (9)
N1—C3—C4—C5−167.68 (12)C9—C2—Cg1—C3176.0 (8)
C2—C3—C4—C57.8 (2)C3—N1—Cg1—C1−179.04 (10)
N3—C4—C5—C60.3 (2)C1—N1—Cg1—C2−179.61 (14)
Cg2—C4—C5—C60.05 (11)C3—N1—Cg1—C21.35 (15)
C3—C4—C5—C6177.53 (12)C1—N1—Cg1—N2−1.17 (14)
C4—C5—C6—C70.2 (2)C3—N1—Cg1—N2179.79 (12)
C5—C6—C7—C8−0.5 (2)C1—N1—Cg1—C3179.04 (10)
C4—N3—C8—C70.2 (2)C2—N2—Cg1—C1179.75 (10)
C6—C7—C8—N30.3 (2)C1—N2—Cg1—C2−179.75 (10)
C13—N4—C9—C100.89 (19)C1—N2—Cg1—N11.19 (14)
C13—N4—C9—C2179.00 (11)C2—N2—Cg1—N1−179.05 (12)
Cg1—C2—C9—N4−154.6 (7)C1—N2—Cg1—C3−179.17 (14)
N2—C2—C9—N4−158.53 (11)C2—N2—Cg1—C30.59 (15)
C3—C2—C9—N420.9 (2)N1—C3—Cg1—C11.58 (16)
Cg1—C2—C9—C1023.6 (8)C2—C3—Cg1—C1−179.24 (14)
N2—C2—C9—C1019.64 (17)C4—C3—Cg1—C1−17.9 (7)
C3—C2—C9—C10−160.96 (13)N1—C3—Cg1—C2−179.18 (9)
N4—C9—C10—C11−0.4 (2)C4—C3—Cg1—C2161.3 (7)
C2—C9—C10—C11−178.53 (11)C2—C3—Cg1—N1179.18 (9)
C9—C10—C11—C120.2 (2)C4—C3—Cg1—N1−19.5 (6)
C10—C11—C12—C13−0.5 (2)N1—C3—Cg1—N2−179.77 (13)
C9—N4—C13—C12−1.2 (2)C2—C3—Cg1—N2−0.59 (15)
C11—C12—C13—N41.0 (2)C4—C3—Cg1—N2160.7 (6)
Cg1, Cg2 and Cg4 are the centroids of the N1/C1,N2,C2,C3, N2/C4–C8 and N4/C9–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C15—H15···N4iii0.952.593.442 (2)149
N1—H1···N4iii0.89 (2)2.73 (2)3.432 (2)137 (1)
C13—H13···N3iv0.952.723.505 (2)141
C16—H16···Cg1iii0.952.883.671 (1)142
C7—H7···Cg4v0.952.793.708 (1)163
C5—H5···N40.952.313.068 (2)137
N1—H1···N30.89 (2)2.37 (2)2.669 (2)100 (1)
C11—H11···Cg2vi0.952.933.772 (1)148
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯N30.89 (2)2.37 (2)2.669 (2)100 (1)
N1—H1⋯N4i0.89 (2)2.73 (2)3.432 (2)137 (1)
C5—H5⋯N40.952.313.068 (2)137
C13—H13⋯N3ii0.952.723.505 (2)141
C15—H15⋯N4i0.952.593.442 (2)149
C7—H7⋯Cg4iii0.952.793.708 (1)163
C11—H11⋯Cg2iv0.952.933.772 (1)148
C16—H16⋯Cg1i0.952.883.671 (1)142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1, Cg2 and Cg4 are the centroids of the N1/C1,N2,C2,C3, N2/C4–C8 and N4/C9–C13 rings, respectively.

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Metal-metal interactions in dinuclear ruthenium complexes containing bridging 4,5-di(2-pyridyl)imidazolates and related ligands.

Authors:  Jonathan W Slater; Deanna M D'Alessandro; F Richard Keene; Peter J Steel
Journal:  Dalton Trans       Date:  2006-01-12       Impact factor: 4.390
  2 in total

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