Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, C13H9N5, the dihedral angle between the pyridyl and benzodi­imidazole rings is 17.76 (7)°. The mol­ecules form a two-dimensional layer structure via N—H...N and C—H...N intermolecular hydrogen bonds. The layers lie parallel to the ab plane and are stacked along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028113/ob6328sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028113/ob6328Isup2.hkl
Contains datablock I

CCDC reference: 232154

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.062
  • wR factor = 0.146
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-(2-pyridyl)benzo[1,2 - d-4,5 - d']diimidazole top
Crystal data top
C13H9N5F(000) = 976
Mr = 235.25Dx = 1.368 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2252 reflections
a = 10.3841 (13) Åθ = 2.7–25.0°
b = 10.0409 (13) ŵ = 0.09 mm1
c = 21.911 (3) ÅT = 293 K
V = 2284.5 (5) Å3Needle, colourless
Z = 80.3 × 0.12 × 0.1 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2701 independent reflections
Radiation source: sealed tube1770 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.099
φ and ω scansθmax = 28.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1311
Tmin = 0.98, Tmax = 0.99k = 1013
12680 measured reflectionsl = 2826
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.07P)2]
where P = (Fo2 + 2Fc2)/3
2701 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.26 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

2.9804 (0.0090) x + 4.1804 (0.0089) y + 18.9027 (0.0101) z = 13.7954 (0.0059)

* -0.0138 (0.0014) C5 * 0.0022 (0.0015) C4 * 0.0125 (0.0017) C3 * -0.0159 (0.0017) C2 * 0.0048 (0.0017) C1 * 0.0102 (0.0015) N1

Rms deviation of fitted atoms = 0.0110

3.9454 (0.0024) x + 1.2737 (0.0051) y + 20.0760 (0.0034) z = 14.0524 (0.0019)

Angle to previous plane (with approximate e.s.d.) = 17.76 (0.07)

* -0.0080 (0.0015) C6 * 0.0143 (0.0013) N3 * 0.0202 (0.0016) C7 * -0.0038 (0.0016) C8 * -0.0115 (0.0016) C9 * -0.0217 (0.0013) N4 * 0.0099 (0.0015) C10 * 0.0215 (0.0014) N5 * -0.0004 (0.0016) C11 * -0.0182 (0.0016) C12 * 0.0078 (0.0016) C13 * -0.0100 (0.0013) N2

Rms deviation of fitted atoms = 0.0140

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1150 (2)0.3116 (3)0.67928 (11)0.0612 (7)
H10.16950.38360.67250.073*
C20.1637 (2)0.2042 (3)0.70961 (10)0.0633 (7)
H20.24940.20230.72180.076*
C30.0835 (2)0.0994 (3)0.72165 (10)0.0598 (7)
H30.11280.02640.74380.072*
C40.04191 (19)0.1036 (2)0.70041 (9)0.0452 (5)
H40.09800.03300.70740.054*
C50.08190 (18)0.2148 (2)0.66866 (8)0.0347 (5)
C60.21266 (18)0.22516 (19)0.64348 (8)0.0335 (5)
C70.40252 (16)0.17938 (19)0.61048 (8)0.0320 (4)
C80.51404 (17)0.11570 (19)0.59141 (9)0.0356 (5)
H80.52590.02410.59440.043*
C90.60633 (17)0.20088 (19)0.56748 (8)0.0329 (5)
C100.77869 (19)0.2933 (2)0.52881 (9)0.0402 (5)
H100.86110.30190.51270.048*
C110.59072 (17)0.33963 (19)0.56230 (8)0.0333 (5)
C120.47745 (17)0.40251 (19)0.57968 (9)0.0356 (5)
H120.46420.49360.57520.043*
C130.38589 (16)0.31791 (18)0.60434 (8)0.0325 (5)
N10.00581 (15)0.3204 (2)0.65858 (8)0.0511 (5)
N20.26342 (13)0.34328 (15)0.62591 (7)0.0365 (4)
H2A0.22630.41980.62780.044*
N30.29158 (14)0.12332 (15)0.63554 (7)0.0348 (4)
N40.72829 (14)0.17509 (17)0.54464 (7)0.0393 (4)
H4A0.76450.09840.54130.047*
N50.70240 (14)0.39612 (16)0.53786 (7)0.0393 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0400 (14)0.0788 (19)0.0647 (16)0.0174 (12)0.0131 (11)0.0135 (14)
C20.0386 (14)0.093 (2)0.0579 (15)0.0026 (13)0.0166 (11)0.0071 (14)
C30.0571 (15)0.0667 (18)0.0556 (14)0.0154 (13)0.0176 (12)0.0091 (13)
C40.0455 (13)0.0438 (13)0.0462 (12)0.0043 (10)0.0049 (9)0.0028 (10)
C50.0309 (11)0.0387 (12)0.0346 (10)0.0022 (8)0.0011 (8)0.0031 (9)
C60.0311 (10)0.0314 (11)0.0382 (10)0.0037 (8)0.0018 (8)0.0011 (8)
C70.0318 (10)0.0298 (11)0.0344 (10)0.0018 (8)0.0041 (8)0.0017 (8)
C80.0349 (10)0.0256 (11)0.0465 (12)0.0022 (8)0.0022 (8)0.0028 (9)
C90.0292 (10)0.0315 (11)0.0380 (10)0.0033 (8)0.0018 (8)0.0021 (9)
C100.0352 (11)0.0413 (12)0.0442 (11)0.0036 (9)0.0081 (9)0.0011 (10)
C110.0314 (10)0.0310 (11)0.0373 (11)0.0027 (8)0.0007 (8)0.0001 (9)
C120.0373 (11)0.0229 (10)0.0464 (12)0.0003 (8)0.0028 (9)0.0016 (8)
C130.0280 (10)0.0295 (11)0.0401 (11)0.0029 (8)0.0011 (8)0.0020 (9)
N10.0361 (11)0.0554 (13)0.0619 (12)0.0070 (8)0.0091 (8)0.0118 (10)
N20.0286 (9)0.0281 (9)0.0530 (10)0.0032 (7)0.0032 (7)0.0001 (7)
N30.0301 (9)0.0302 (9)0.0440 (9)0.0022 (7)0.0005 (7)0.0023 (7)
N40.0312 (9)0.0353 (10)0.0514 (10)0.0038 (7)0.0057 (7)0.0008 (8)
N50.0355 (9)0.0342 (10)0.0482 (10)0.0036 (7)0.0089 (7)0.0001 (8)
Geometric parameters (Å, º) top
C1—N11.337 (3)C7—C131.408 (3)
C1—C21.364 (3)C8—C91.387 (3)
C1—H10.9300C8—H80.9300
C2—C31.368 (3)C9—N41.386 (2)
C2—H20.9300C9—C111.407 (3)
C3—C41.383 (3)C10—N51.316 (2)
C3—H30.9300C10—N41.343 (2)
C4—C51.380 (3)C10—H100.9300
C4—H40.9300C11—C121.388 (2)
C5—N11.340 (3)C11—N51.398 (2)
C5—C61.469 (3)C12—C131.385 (2)
C6—N31.322 (2)C12—H120.9300
C6—N21.354 (2)C13—N21.381 (2)
C7—C81.387 (2)N2—H2A0.8600
C7—N31.395 (2)N4—H4A0.8600
N1—C1—C2124.4 (2)N4—C9—C8130.72 (17)
N1—C1—H1117.8N4—C9—C11105.14 (15)
C2—C1—H1117.8C8—C9—C11124.14 (16)
C1—C2—C3118.5 (2)N5—C10—N4114.82 (17)
C1—C2—H2120.8N5—C10—H10122.6
C3—C2—H2120.8N4—C10—H10122.6
C2—C3—C4119.0 (2)C12—C11—N5128.58 (18)
C2—C3—H3120.5C12—C11—C9121.72 (16)
C4—C3—H3120.5N5—C11—C9109.70 (15)
C5—C4—C3118.5 (2)C13—C12—C11114.19 (18)
C5—C4—H4120.7C13—C12—H12122.9
C3—C4—H4120.7C11—C12—H12122.9
N1—C5—C4123.08 (18)N2—C13—C12130.77 (17)
N1—C5—C6115.28 (17)N2—C13—C7105.22 (15)
C4—C5—C6121.64 (18)C12—C13—C7123.99 (16)
N3—C6—N2113.51 (16)C1—N1—C5116.43 (19)
N3—C6—C5124.59 (17)C6—N2—C13107.12 (15)
N2—C6—C5121.90 (17)C6—N2—H2A126.4
C8—C7—N3128.46 (18)C13—N2—H2A126.4
C8—C7—C13121.93 (16)C6—N3—C7104.57 (15)
N3—C7—C13109.57 (15)C10—N4—C9106.51 (16)
C7—C8—C9113.97 (18)C10—N4—H4A126.7
C7—C8—H8123.0C9—N4—H4A126.7
C9—C8—H8123.0C10—N5—C11103.82 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N3i0.862.062.877 (2)159
N4—H4A···N5ii0.862.062.896 (2)163
C8—H8···N1iii0.932.503.317 (3)146
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+3/2, y1/2, z; (iii) x+1/2, y1/2, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds