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The title compound, C20H14N4, lies about an inversion centre and the benz­imidazole moiety and the phenyl ring are twisted by 30.9 (1)°. The benz­imidazole moiety is completely planar, with a maximum deviation of 0.009 (2) Å. Intermolecular N-­H...N hydrogen bonds give rise to a layered structure, with the layers stacked by van der Waals interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003978/sk1369sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003978/sk1369Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108270100003978/sk1369sup3.pdf
Supplementary material

CCDC reference: 146071

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

(I) top
Crystal data top
C20H14N4F(000) = 648
Mr = 310.35Dx = 1.374 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3853 reflections
a = 10.2400 (3) Åθ = 2.7–28.3°
b = 9.7505 (2) ŵ = 0.09 mm1
c = 15.0310 (4) ÅT = 293 K
V = 1500.77 (7) Å3Needle, dark red
Z = 40.50 × 0.12 × 0.10 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
1223 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.076
Graphite monochromatorθmax = 28.3°, θmin = 2.7°
Detector resolution: 8.33 pixels mm-1h = 913
ω scansk = 1212
9577 measured reflectionsl = 1919
1846 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0584P)2 + 0.4289P]
where P = (Fo2 + 2Fc2)/3
1846 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

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. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.16043 (17)0.05717 (17)0.41094 (13)0.0389 (5)
N20.20392 (17)0.16702 (16)0.39828 (12)0.0377 (5)
H2A0.24670.24280.40130.045*
C10.07906 (19)0.1500 (2)0.36575 (14)0.0353 (5)
C20.0120 (2)0.2423 (2)0.33129 (15)0.0442 (6)
H2B0.00620.33550.32720.053*
C30.1289 (2)0.1899 (2)0.30385 (17)0.0477 (6)
H3A0.19130.24860.27990.057*
C40.1571 (2)0.0490 (2)0.31097 (17)0.0491 (6)
H4A0.23740.01630.29120.059*
C50.0685 (2)0.0409 (2)0.34651 (17)0.0458 (6)
H5A0.08840.13350.35230.055*
C60.0526 (2)0.0099 (2)0.37380 (15)0.0361 (5)
C70.2466 (2)0.04138 (19)0.42458 (14)0.0341 (5)
C80.37635 (19)0.02064 (19)0.46375 (14)0.0330 (5)
C90.4812 (2)0.1039 (2)0.43866 (16)0.0391 (5)
H9A0.46800.17670.39670.047*
C100.3967 (2)0.0829 (2)0.52542 (15)0.0383 (5)
H10A0.32510.13960.54400.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0270 (9)0.0259 (9)0.0638 (12)0.0013 (7)0.0035 (8)0.0009 (8)
N20.0304 (9)0.0240 (8)0.0587 (11)0.0004 (7)0.0025 (8)0.0006 (8)
C10.0299 (11)0.0272 (10)0.0488 (12)0.0021 (8)0.0002 (9)0.0025 (9)
C20.0437 (13)0.0302 (11)0.0588 (15)0.0065 (10)0.0068 (11)0.0008 (10)
C30.0393 (13)0.0445 (13)0.0594 (15)0.0134 (10)0.0090 (11)0.0019 (12)
C40.0321 (12)0.0512 (14)0.0640 (15)0.0023 (10)0.0091 (11)0.0079 (12)
C50.0354 (13)0.0332 (11)0.0688 (16)0.0013 (9)0.0041 (11)0.0026 (11)
C60.0277 (10)0.0288 (10)0.0516 (13)0.0017 (8)0.0009 (9)0.0014 (9)
C70.0286 (11)0.0241 (9)0.0496 (12)0.0009 (8)0.0005 (9)0.0002 (9)
C80.0261 (10)0.0254 (9)0.0475 (12)0.0002 (8)0.0006 (9)0.0009 (9)
C90.0340 (12)0.0290 (10)0.0545 (13)0.0046 (9)0.0018 (10)0.0088 (10)
C100.0291 (11)0.0329 (11)0.0529 (13)0.0051 (9)0.0034 (10)0.0043 (9)
Geometric parameters (Å, º) top
N1—C71.320 (3)C4—C51.370 (3)
N1—C61.400 (3)C4—H4A0.9300
N2—C71.359 (2)C5—C61.396 (3)
N2—C11.379 (3)C5—H5A0.9300
N2—H2A0.8600C7—C81.468 (3)
C1—C21.395 (3)C8—C101.386 (3)
C1—C61.398 (3)C8—C91.398 (3)
C2—C31.365 (3)C9—C10i1.377 (3)
C2—H2B0.9300C9—H9A0.9600
C3—C41.409 (3)C10—C9i1.377 (3)
C3—H3A0.9300C10—H10A0.9600
C7—N1—C6104.4 (2)C4—C5—H5A120.8
C7—N2—C1107.0 (2)C6—C5—H5A120.8
C7—N2—H2A126.5C5—C6—C1119.57 (19)
C1—N2—H2A126.5C5—C6—N1130.68 (19)
N2—C1—C2132.37 (19)C1—C6—N1109.75 (17)
N2—C1—C6105.46 (17)N1—C7—N2113.34 (18)
C2—C1—C6122.16 (19)N1—C7—C8124.54 (17)
C3—C2—C1117.2 (2)N2—C7—C8122.13 (17)
C3—C2—H2B121.4C10—C8—C9119.20 (19)
C1—C2—H2B121.4C10—C8—C7120.32 (18)
C2—C3—C4121.5 (2)C9—C8—C7120.48 (19)
C2—C3—H3A119.3C10i—C9—C8120.4 (2)
C4—C3—H3A119.3C10i—C9—H9A119.7
C5—C4—C3121.2 (2)C8—C9—H9A120.0
C5—C4—H4A119.4C9i—C10—C8120.45 (19)
C3—C4—H4A119.4C9i—C10—H10A119.6
C4—C5—C6118.4 (2)C8—C10—H10A119.9
C7—N2—C1—C2179.0 (2)C7—N1—C6—C10.4 (2)
C7—N2—C1—C60.5 (2)C6—N1—C7—N20.7 (2)
N2—C1—C2—C3179.5 (2)C6—N1—C7—C8179.5 (2)
C6—C1—C2—C31.1 (3)C1—N2—C7—N10.8 (3)
C1—C2—C3—C40.7 (4)C1—N2—C7—C8179.42 (19)
C2—C3—C4—C50.6 (4)N1—C7—C8—C1030.6 (3)
C3—C4—C5—C61.5 (4)N2—C7—C8—C10149.6 (2)
C4—C5—C6—C11.1 (3)N1—C7—C8—C9148.6 (2)
C4—C5—C6—N1179.3 (2)N2—C7—C8—C931.1 (3)
N2—C1—C6—C5179.7 (2)C10—C8—C9—C10i0.2 (4)
C2—C1—C6—C50.2 (3)C7—C8—C9—C10i179.1 (2)
N2—C1—C6—N10.1 (2)C9—C8—C10—C9i0.2 (4)
C2—C1—C6—N1179.5 (2)C7—C8—C10—C9i179.1 (2)
C7—N1—C6—C5179.2 (2)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1ii0.862.173.033 (2)175
Symmetry code: (ii) x+1/2, y1/2, z.
 

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