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The title compound, C26H24N4, contains one pyrazole ring and two phenyl rings, which are nearly perpendicular to the benzimidazole ring system. In the structure, there is one intra­molecular C—H...N hydrogen-bonding inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023706/bt6704sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023706/bt6704Isup2.hkl
Contains datablock I

CCDC reference: 282258

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.130
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N3 - N4 .. 13.35 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N4 - C11 .. 13.64 su
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.120 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4A ... ?
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-Benzyl-2-[1-(5-methyl-1H-pyrazol-3-yl)-2-phenylethyl]benzimidazole top
Crystal data top
C26H24N4Z = 2
Mr = 392.49F(000) = 416
Triclinic, P1Dx = 1.219 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.244 (5) ÅCell parameters from 21742 reflections
b = 10.601 (5) Åθ = 2.2–27.9°
c = 11.404 (5) ŵ = 0.07 mm1
α = 64.499 (5)°T = 296 K
β = 74.587 (5)°Prism, colourless
γ = 89.556 (5)°0.62 × 0.53 × 0.47 mm
V = 1069.5 (9) Å3
Data collection top
Stoe IPDS-II
diffractometer
3537 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focusRint = 0.120
Plane graphite monochromatorθmax = 27.8°, θmin = 2.5°
Detector resolution: 6.67 pixels mm-1h = 1313
ω scansk = 1313
17823 measured reflectionsl = 1414
4925 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0685P)2 + 0.0775P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4925 reflectionsΔρmax = 0.24 e Å3
273 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (5)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.15104 (11)0.25192 (14)0.84680 (13)0.0551 (4)
N20.37136 (10)0.30826 (11)0.72481 (11)0.0433 (3)
N30.30782 (14)0.68272 (14)0.62471 (14)0.0638 (4)
N40.23158 (14)0.77030 (12)0.54349 (12)0.0589 (4)
C10.32488 (13)0.19085 (14)0.71697 (13)0.0463 (4)
C20.38997 (17)0.11345 (17)0.65128 (17)0.0626 (5)
C30.3108 (2)0.00066 (19)0.6651 (2)0.0734 (7)
C40.1740 (2)0.03397 (19)0.7405 (2)0.0735 (6)
C50.11044 (17)0.04269 (18)0.80536 (18)0.0651 (6)
C60.18809 (13)0.15788 (15)0.79274 (15)0.0498 (4)
C70.26220 (12)0.33793 (14)0.80472 (13)0.0444 (4)
C80.26849 (13)0.46503 (15)0.83118 (15)0.0507 (4)
C90.21949 (14)0.58189 (14)0.72643 (14)0.0506 (4)
C100.08652 (16)0.59911 (17)0.71590 (16)0.0603 (5)
C110.10042 (18)0.71727 (17)0.60033 (17)0.0643 (6)
C120.0007 (3)0.7942 (3)0.5298 (2)0.0941 (8)
C130.18329 (15)0.43342 (17)0.97635 (15)0.0578 (5)
C140.24215 (14)0.33442 (16)1.08429 (15)0.0535 (4)
C150.3237 (2)0.3852 (2)1.1379 (2)0.0758 (7)
C160.3790 (2)0.2947 (3)1.2352 (3)0.0957 (9)
C170.3560 (2)0.1516 (3)1.2810 (2)0.0903 (8)
C180.2770 (2)0.0997 (2)1.2287 (2)0.0818 (7)
C190.21962 (18)0.19002 (18)1.13281 (17)0.0679 (5)
C200.51037 (13)0.37901 (14)0.66243 (13)0.0476 (4)
C210.60646 (13)0.32036 (14)0.74780 (14)0.0482 (4)
C220.74445 (15)0.3639 (2)0.68612 (19)0.0658 (5)
C230.83745 (17)0.3166 (3)0.7591 (3)0.0827 (8)
C240.7943 (2)0.2264 (3)0.8930 (3)0.0899 (9)
C250.6587 (2)0.1817 (3)0.9557 (2)0.0895 (8)
C260.56388 (17)0.22785 (19)0.88297 (18)0.0687 (5)
H20.481500.136500.601000.0750*
H30.350000.053900.622600.0880*
H40.124300.111100.747300.0880*
H4A0.264100.845800.469200.0710*
H50.019000.018700.855800.0780*
H80.363700.493100.819600.0610*
H100.006300.541400.775700.0720*
H12A0.008100.889700.517200.1410*
H12B0.090100.748900.583600.1410*
H12C0.019600.793600.442900.1410*
H13A0.176000.521300.983600.0690*
H13B0.091900.393000.992400.0690*
H150.341000.481801.107600.0910*
H160.432700.330601.270600.1150*
H170.393900.090801.346900.1080*
H180.261900.003101.257900.0980*
H190.164100.153001.099700.0810*
H20A0.508000.477800.641500.0570*
H20B0.546900.373600.577300.0570*
H220.775100.425900.594200.0790*
H230.930000.346900.716200.0990*
H240.857000.195000.942100.1080*
H250.629200.119801.047800.1070*
H260.471600.195800.926300.0820*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0381 (6)0.0676 (7)0.0729 (8)0.0064 (5)0.0153 (5)0.0438 (6)
N20.0369 (5)0.0483 (5)0.0487 (6)0.0083 (4)0.0125 (4)0.0253 (5)
N30.0602 (8)0.0604 (7)0.0644 (8)0.0037 (6)0.0059 (6)0.0289 (6)
N40.0696 (8)0.0442 (6)0.0484 (6)0.0000 (5)0.0060 (6)0.0138 (5)
C10.0480 (7)0.0478 (7)0.0501 (7)0.0108 (5)0.0202 (5)0.0248 (6)
C20.0628 (9)0.0620 (9)0.0688 (9)0.0114 (7)0.0120 (7)0.0385 (8)
C30.0870 (13)0.0677 (10)0.0846 (12)0.0141 (9)0.0241 (10)0.0515 (9)
C40.0866 (12)0.0649 (9)0.0873 (12)0.0017 (8)0.0359 (10)0.0440 (9)
C50.0566 (9)0.0678 (9)0.0824 (11)0.0013 (7)0.0243 (8)0.0412 (9)
C60.0445 (7)0.0563 (7)0.0592 (8)0.0077 (5)0.0217 (6)0.0313 (6)
C70.0349 (6)0.0533 (7)0.0523 (7)0.0091 (5)0.0142 (5)0.0292 (6)
C80.0403 (6)0.0584 (8)0.0620 (8)0.0049 (5)0.0114 (6)0.0366 (7)
C90.0502 (7)0.0510 (7)0.0557 (7)0.0032 (6)0.0067 (6)0.0332 (6)
C100.0530 (8)0.0602 (8)0.0608 (9)0.0079 (6)0.0089 (7)0.0251 (7)
C110.0765 (11)0.0605 (9)0.0604 (9)0.0184 (8)0.0154 (8)0.0337 (7)
C120.1039 (16)0.0928 (14)0.0806 (13)0.0416 (12)0.0318 (12)0.0317 (11)
C130.0544 (8)0.0666 (9)0.0609 (8)0.0151 (7)0.0133 (7)0.0381 (7)
C140.0468 (7)0.0609 (8)0.0565 (8)0.0053 (6)0.0082 (6)0.0333 (7)
C150.0855 (12)0.0666 (10)0.0842 (12)0.0009 (9)0.0341 (10)0.0360 (9)
C160.0855 (14)0.1117 (17)0.1003 (15)0.0003 (12)0.0490 (12)0.0435 (14)
C170.0800 (13)0.0960 (15)0.0821 (13)0.0251 (11)0.0292 (11)0.0251 (11)
C180.0971 (14)0.0581 (9)0.0706 (11)0.0091 (9)0.0102 (10)0.0192 (9)
C190.0715 (10)0.0636 (9)0.0649 (9)0.0064 (8)0.0100 (8)0.0306 (8)
C200.0402 (6)0.0502 (7)0.0471 (7)0.0049 (5)0.0065 (5)0.0204 (6)
C210.0394 (6)0.0531 (7)0.0596 (8)0.0094 (5)0.0140 (6)0.0322 (6)
C220.0443 (8)0.0803 (10)0.0783 (10)0.0023 (7)0.0113 (7)0.0438 (9)
C230.0414 (8)0.1148 (16)0.1172 (17)0.0142 (9)0.0277 (9)0.0717 (15)
C240.0684 (12)0.1205 (17)0.1149 (18)0.0389 (12)0.0545 (12)0.0674 (16)
C250.0838 (14)0.1036 (15)0.0776 (12)0.0297 (11)0.0411 (11)0.0273 (11)
C260.0504 (8)0.0793 (11)0.0628 (9)0.0134 (7)0.0176 (7)0.0188 (8)
Geometric parameters (Å, º) top
N1—C61.385 (2)C21—C261.370 (2)
N1—C71.307 (2)C21—C221.381 (2)
N2—C11.383 (2)C22—C231.381 (3)
N2—C71.3710 (19)C23—C241.354 (4)
N2—C201.4543 (19)C24—C251.362 (3)
N3—N41.401 (2)C25—C261.394 (3)
N3—C91.302 (2)C2—H20.9300
N4—C111.333 (2)C3—H30.9300
N4—H4A0.8600C4—H40.9300
C1—C21.391 (3)C5—H50.9300
C1—C61.392 (2)C8—H80.9800
C2—C31.377 (3)C10—H100.9300
C3—C41.391 (3)C12—H12A0.9600
C4—C51.373 (3)C12—H12B0.9600
C5—C61.396 (3)C12—H12C0.9600
C7—C81.508 (2)C13—H13A0.9700
C8—C91.500 (2)C13—H13B0.9700
C8—C131.541 (2)C15—H150.9300
C9—C101.403 (2)C16—H160.9300
C10—C111.345 (3)C17—H170.9300
C11—C121.488 (4)C18—H180.9300
C13—C141.501 (2)C19—H190.9300
C14—C191.382 (3)C20—H20A0.9700
C14—C151.387 (3)C20—H20B0.9700
C15—C161.372 (4)C22—H220.9300
C16—C171.374 (5)C23—H230.9300
C17—C181.364 (3)C24—H240.9300
C18—C191.375 (3)C25—H250.9300
C20—C211.511 (2)C26—H260.9300
N1···N22.241 (2)H3···N3viii2.8200
N1···C193.306 (3)H3···N4viii2.8000
N2···N12.241 (2)H4···C11viii3.0000
N4···C22i3.435 (3)H4A···C17ix3.0000
N1···H192.6500H4A···C18ix2.8700
N1···H13B2.6400H4A···H17ix2.5300
N1···H24ii2.8900H4A···H18ix2.2700
N2···H262.5800H4A···H2i2.5000
N3···H3iii2.8200H5···H19x2.4200
N3···H20Bi2.6900H8···C202.7100
N3···H2i2.8000H8···H20A2.2400
N4···H3iii2.8000H8···H16xi2.4800
N4···H2i2.9000H10···C23ii3.0600
C1···C263.585 (3)H10···C13v3.0900
C7···C193.277 (3)H12A···H12Axii2.2100
C7···C263.496 (3)H12B···C16v3.0300
C19···C73.277 (3)H12C···C23i3.0500
C19···N13.306 (3)H13A···H152.4000
C20···C20i3.547 (3)H13B···N12.6400
C22···N4i3.435 (3)H13B···C102.9800
C26···C13.585 (3)H13B···H192.5100
C26···C73.496 (3)H15···H13A2.4000
C2···H20B2.8700H16···H8xi2.4800
C2···H17iv3.0800H17···H4Avi2.5300
C5···H24iv3.0000H17···C2iv3.0800
C7···H262.9200H18···H4Avi2.2700
C7···H192.9500H19···N12.6500
C8···H20A2.7700H19···C72.9500
C10···H13B2.9800H19···H13B2.5100
C11···H4iii3.0000H19···H5x2.4200
C13···H10v3.0900H20A···C82.7700
C16···H12Bv3.0300H20A···H82.2400
C17···H4Avi3.0000H20A···H20Bi2.5200
C18···H4Avi2.8700H20B···C22.8700
C19···H262.9800H20B···H22.4900
C20···H20Bi3.0600H20B···H222.4800
C20···H82.7100H20B···N3i2.6900
C20···H22.9800H20B···C20i3.0600
C23···H12Ci3.0500H20B···H20Ai2.5200
C23···H10vii3.0600H22···H20B2.4800
H2···C202.9800H24···N1vii2.8900
H2···H20B2.4900H24···C5iv3.0000
H2···N3i2.8000H26···N22.5800
H2···N4i2.9000H26···C72.9200
H2···H4Ai2.5000H26···C192.9800
C6—N1—C7104.67 (12)C1—C2—H2122.00
C1—N2—C7105.93 (11)C3—C2—H2122.00
C1—N2—C20125.09 (12)C2—C3—H3119.00
C7—N2—C20128.96 (13)C4—C3—H3119.00
N4—N3—C9105.52 (13)C3—C4—H4119.00
N3—N4—C11108.75 (13)C5—C4—H4119.00
N3—N4—H4A126.00C4—C5—H5121.00
C11—N4—H4A126.00C6—C5—H5121.00
C2—C1—C6122.79 (15)C7—C8—H8109.00
N2—C1—C2131.71 (14)C9—C8—H8109.00
N2—C1—C6105.50 (13)C13—C8—H8109.00
C1—C2—C3116.03 (16)C9—C10—H10128.00
C2—C3—C4122.0 (2)C11—C10—H10128.00
C3—C4—C5121.7 (2)C11—C12—H12A110.00
C4—C5—C6117.57 (17)C11—C12—H12B109.00
C1—C6—C5119.93 (16)C11—C12—H12C110.00
N1—C6—C1110.28 (14)H12A—C12—H12B109.00
N1—C6—C5129.79 (14)H12A—C12—H12C109.00
N2—C7—C8122.51 (12)H12B—C12—H12C109.00
N1—C7—C8123.69 (13)C8—C13—H13A109.00
N1—C7—N2113.63 (14)C8—C13—H13B109.00
C7—C8—C13111.67 (13)C14—C13—H13A109.00
C9—C8—C13111.59 (13)C14—C13—H13B109.00
C7—C8—C9107.48 (12)H13A—C13—H13B108.00
C8—C9—C10129.23 (14)C14—C15—H15120.00
N3—C9—C8119.42 (14)C16—C15—H15120.00
N3—C9—C10111.30 (14)C15—C16—H16120.00
C9—C10—C11104.88 (15)C17—C16—H16120.00
N4—C11—C12117.71 (17)C16—C17—H17120.00
C10—C11—C12132.74 (19)C18—C17—H17120.00
N4—C11—C10109.55 (16)C17—C18—H18120.00
C8—C13—C14113.53 (14)C19—C18—H18120.00
C13—C14—C19121.86 (15)C14—C19—H19119.00
C13—C14—C15120.85 (17)C18—C19—H19119.00
C15—C14—C19117.28 (16)N2—C20—H20A109.00
C14—C15—C16120.8 (2)N2—C20—H20B109.00
C15—C16—C17120.8 (2)C21—C20—H20A109.00
C16—C17—C18119.2 (2)C21—C20—H20B108.00
C17—C18—C19120.1 (2)H20A—C20—H20B108.00
C14—C19—C18121.77 (18)C21—C22—H22120.00
N2—C20—C21115.01 (11)C23—C22—H22120.00
C20—C21—C22118.01 (13)C22—C23—H23120.00
C22—C21—C26118.47 (15)C24—C23—H23120.00
C20—C21—C26123.52 (13)C23—C24—H24120.00
C21—C22—C23120.90 (19)C25—C24—H24120.00
C22—C23—C24120.2 (2)C24—C25—H25120.00
C23—C24—C25119.8 (2)C26—C25—H25120.00
C24—C25—C26120.5 (2)C21—C26—H26120.00
C21—C26—C25120.05 (17)C25—C26—H26120.00
C6—N1—C7—N20.51 (16)N1—C7—C8—C1340.48 (19)
C7—N1—C6—C10.08 (16)N2—C7—C8—C992.64 (15)
C7—N1—C6—C5179.46 (16)C7—C8—C13—C1469.21 (17)
C6—N1—C7—C8175.79 (13)C9—C8—C13—C14170.47 (14)
C1—N2—C7—C8176.09 (12)C7—C8—C9—N3103.74 (16)
C1—N2—C7—N10.75 (16)C7—C8—C9—C1073.2 (2)
C20—N2—C7—N1178.87 (12)C13—C8—C9—N3133.50 (16)
C20—N2—C1—C21.2 (2)C13—C8—C9—C1049.5 (2)
C20—N2—C7—C85.8 (2)N3—C9—C10—C110.2 (2)
C7—N2—C1—C2179.46 (16)C8—C9—C10—C11176.95 (17)
C7—N2—C20—C2190.54 (18)C9—C10—C11—C12179.8 (2)
C7—N2—C1—C60.64 (14)C9—C10—C11—N40.4 (2)
C20—N2—C1—C6178.85 (12)C8—C13—C14—C1982.8 (2)
C1—N2—C20—C2187.25 (16)C8—C13—C14—C1596.2 (2)
C9—N3—N4—C110.26 (18)C13—C14—C15—C16179.09 (19)
N4—N3—C9—C8177.50 (14)C13—C14—C19—C18177.99 (17)
N4—N3—C9—C100.02 (19)C15—C14—C19—C181.0 (3)
N3—N4—C11—C12179.76 (18)C19—C14—C15—C160.1 (3)
N3—N4—C11—C100.4 (2)C14—C15—C16—C170.6 (4)
C2—C1—C6—C50.1 (2)C15—C16—C17—C180.1 (4)
C6—C1—C2—C30.1 (2)C16—C17—C18—C191.0 (3)
N2—C1—C2—C3179.82 (16)C17—C18—C19—C141.6 (3)
C2—C1—C6—N1179.72 (14)N2—C20—C21—C22167.97 (16)
N2—C1—C6—N10.36 (16)N2—C20—C21—C2612.8 (2)
N2—C1—C6—C5179.95 (14)C20—C21—C22—C23178.6 (2)
C1—C2—C3—C40.1 (3)C26—C21—C22—C230.7 (3)
C2—C3—C4—C50.0 (3)C20—C21—C26—C25178.1 (2)
C3—C4—C5—C60.2 (3)C22—C21—C26—C251.1 (3)
C4—C5—C6—N1179.77 (17)C21—C22—C23—C240.1 (4)
C4—C5—C6—C10.3 (2)C22—C23—C24—C250.3 (5)
N2—C7—C8—C13144.65 (13)C23—C24—C25—C260.2 (5)
N1—C7—C8—C982.23 (16)C24—C25—C26—C210.9 (4)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z; (iii) x, y+1, z; (iv) x+1, y, z+2; (v) x, y+1, z+2; (vi) x, y1, z+1; (vii) x+1, y, z; (viii) x, y1, z; (ix) x, y+1, z1; (x) x, y, z+2; (xi) x+1, y+1, z+2; (xii) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26—H26···N20.932.582.900 (3)101
 

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