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The title compound, C11H8N2, contains two essentially planar mol­ecules (A and B) in the asymmetric unit. Molecules of type B exhibit π–π stacking and form infinite zigzag chains along the a axis. A and B mol­ecules are linked by Namine—H...Nimine hydrogen bonds and form polymeric –ABAB– criss-crossed chains approximately along the [110] and [\overline110] directions. The A mol­ecules show little evidence of π stacking and, in addition to the hydrogen bonds, appear to be held in the crystal structure primarily by C—H...π interactions. The geometric parameters of mol­ecules A and B agree well with each other and, where comparisons are appropriate, with those of a naphthimidazolium cation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804019555/lh6257sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804019555/lh6257Isup2.hkl
Contains datablock I

CCDC reference: 251760

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.046
  • wR factor = 0.110
  • Data-to-parameter ratio = 6.1

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.778 1.000 Tmin' and Tmax expected: 0.962 0.998 RR' = 0.808 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.09 PLAT128_ALERT_4_C Non-standard setting of Space group Cc .... Ia PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.09 From the CIF: _reflns_number_total 1480 Count of symmetry unique reflns 1489 Completeness (_total/calc) 99.40% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

1H–napth[2,3-d]imidazole top
Crystal data top
C11H8N2F(000) = 704
Mr = 168.19Dx = 1.342 Mg m3
Monoclinic, IaMo Kα radiation, λ = 0.71073 Å
Hall symbol: I -2yaCell parameters from 730 reflections
a = 9.4503 (6) Åθ = 2.3–20.8°
b = 16.3882 (8) ŵ = 0.08 mm1
c = 11.4770 (9) ÅT = 295 K
β = 110.502 (4)°Plate, pale yellow
V = 1664.90 (19) Å30.47 × 0.22 × 0.02 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1480 independent reflections
Radiation source: fine-focus sealed tube1145 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
φ and ω scansθmax = 25.1°, θmin = 3.8°
Absorption correction: multi-scan
(SADABS; Blessing 1995)
h = 1110
Tmin = 0.778, Tmax = 1.00k = 1919
5846 measured reflectionsl = 1313
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0653P)2]
where P = (Fo2 + 2Fc2)/3
1480 reflections(Δ/σ)max < 0.001
243 parametersΔρmax = 0.14 e Å3
2 restraintsΔρmin = 0.13 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.7357 (4)0.2087 (2)0.8088 (3)0.0461 (9)
N130.6300 (4)0.1046 (2)0.6851 (3)0.0482 (9)
C110.6057 (4)0.1915 (2)0.8331 (3)0.0387 (10)
C120.7428 (5)0.1565 (3)0.7215 (4)0.0480 (10)
H120.82050.15690.68940.058*
C130.5392 (4)0.1247 (2)0.7551 (3)0.0395 (10)
C140.4075 (5)0.0916 (2)0.7566 (3)0.0453 (10)
H140.36310.04800.70490.054*
C150.3398 (5)0.1246 (3)0.8379 (3)0.0444 (10)
C15A0.2020 (5)0.0934 (3)0.8434 (4)0.0539 (12)
H15A0.15510.05010.79200.065*
C15B0.1376 (6)0.1247 (3)0.9207 (4)0.0606 (13)
H15B0.04740.10300.92220.073*
C160.4103 (5)0.1912 (2)0.9175 (3)0.0435 (10)
C16A0.3385 (6)0.2219 (3)0.9996 (4)0.0532 (12)
H16A0.38370.26411.05400.064*
C16B0.2058 (6)0.1904 (3)0.9995 (4)0.0634 (14)
H16B0.15950.21231.05190.076*
C170.5450 (5)0.2252 (2)0.9143 (3)0.0456 (11)
H170.59130.26880.96520.055*
H110.797 (6)0.245 (3)0.844 (4)0.056 (14)*
N210.4759 (4)0.0239 (2)0.5107 (3)0.0481 (9)
N230.3630 (4)0.1421 (2)0.4366 (3)0.0496 (9)
C210.3392 (4)0.0028 (3)0.4217 (3)0.0431 (10)
C220.4817 (5)0.1065 (3)0.5137 (4)0.0471 (11)
H220.56390.13540.56650.057*
C230.2681 (4)0.0775 (2)0.3758 (3)0.0409 (10)
C240.1293 (5)0.0783 (3)0.2820 (4)0.0462 (11)
H240.08200.12750.25090.055*
C250.0602 (4)0.0038 (3)0.2341 (3)0.0443 (11)
C25A0.0828 (5)0.0003 (3)0.1375 (4)0.0543 (12)
H25A0.13210.04880.10510.065*
C25B0.1492 (5)0.0711 (3)0.0911 (4)0.0604 (13)
H25B0.24200.07120.02640.072*
C260.1329 (5)0.0719 (3)0.2832 (3)0.0446 (10)
C26A0.0573 (5)0.1453 (3)0.2326 (4)0.0548 (12)
H26A0.10240.19500.26380.066*
C26B0.0798 (5)0.1449 (3)0.1393 (4)0.0598 (12)
H26B0.12740.19400.10770.072*
C270.2754 (5)0.0711 (3)0.3780 (4)0.0477 (11)
H270.32500.11950.41030.057*
H210.543 (6)0.010 (3)0.552 (4)0.071 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.044 (2)0.039 (2)0.0478 (19)0.0121 (17)0.0060 (16)0.0105 (17)
N130.053 (2)0.041 (2)0.0464 (17)0.0035 (18)0.0119 (16)0.0088 (16)
C110.043 (2)0.027 (2)0.038 (2)0.0010 (18)0.0050 (18)0.0029 (16)
C120.048 (2)0.050 (3)0.046 (2)0.005 (2)0.0170 (18)0.003 (2)
C130.043 (2)0.033 (2)0.0338 (18)0.0022 (18)0.0022 (17)0.0014 (15)
C140.048 (3)0.038 (2)0.039 (2)0.009 (2)0.0030 (17)0.0051 (18)
C150.043 (2)0.045 (2)0.0372 (18)0.006 (2)0.0042 (16)0.0081 (18)
C15A0.045 (3)0.059 (3)0.051 (2)0.002 (2)0.009 (2)0.006 (2)
C15B0.050 (3)0.063 (3)0.067 (3)0.005 (3)0.018 (2)0.016 (3)
C160.052 (2)0.037 (2)0.0363 (18)0.004 (2)0.0087 (17)0.0019 (17)
C16A0.073 (3)0.037 (2)0.050 (2)0.011 (2)0.022 (2)0.0023 (19)
C16B0.075 (4)0.057 (3)0.069 (3)0.020 (3)0.040 (3)0.019 (2)
C170.053 (3)0.032 (2)0.042 (2)0.001 (2)0.0042 (18)0.0027 (18)
N210.045 (2)0.045 (2)0.0471 (19)0.0099 (18)0.0080 (16)0.0148 (17)
N230.054 (2)0.042 (2)0.0468 (18)0.0066 (17)0.0103 (16)0.0059 (16)
C210.044 (3)0.043 (2)0.040 (2)0.007 (2)0.011 (2)0.0076 (19)
C220.049 (2)0.047 (3)0.041 (2)0.004 (2)0.0107 (18)0.0022 (19)
C230.045 (2)0.037 (2)0.0387 (19)0.0041 (19)0.0132 (17)0.0057 (18)
C240.051 (3)0.036 (2)0.050 (2)0.0134 (19)0.015 (2)0.0082 (18)
C250.047 (2)0.047 (3)0.042 (2)0.009 (2)0.0190 (19)0.0058 (19)
C25A0.053 (3)0.054 (3)0.050 (2)0.008 (2)0.013 (2)0.004 (2)
C25B0.057 (3)0.067 (3)0.049 (2)0.011 (3)0.008 (2)0.004 (2)
C260.052 (3)0.047 (3)0.041 (2)0.001 (2)0.022 (2)0.0044 (19)
C26A0.070 (3)0.042 (3)0.060 (2)0.000 (2)0.032 (2)0.005 (2)
C26B0.071 (3)0.049 (3)0.055 (2)0.010 (3)0.017 (2)0.004 (2)
C270.053 (3)0.040 (3)0.048 (2)0.010 (2)0.017 (2)0.009 (2)
Geometric parameters (Å, º) top
N11—C121.337 (5)N21—C221.355 (5)
N11—C111.381 (5)N21—C211.381 (5)
N11—H110.83 (5)N21—H210.85 (5)
N13—C121.313 (5)N23—C221.299 (5)
N13—C131.404 (5)N23—C231.405 (5)
C11—C171.369 (6)C21—C271.368 (6)
C11—C131.415 (5)C21—C231.406 (5)
C12—H120.9300C22—H220.9300
C13—C141.363 (6)C23—C241.375 (5)
C14—C151.412 (6)C24—C251.403 (6)
C14—H140.9300C24—H240.9300
C15—C15A1.421 (6)C25—C25A1.417 (6)
C15—C161.430 (6)C25—C261.434 (6)
C15A—C15B1.341 (7)C25A—C25B1.346 (6)
C15A—H15A0.9300C25A—H25A0.9300
C15B—C16B1.409 (7)C25B—C26B1.395 (7)
C15B—H15B0.9300C25B—H25B0.9300
C16—C171.402 (6)C26—C271.404 (6)
C16—C16A1.431 (6)C26—C26A1.416 (7)
C16A—C16B1.356 (7)C26A—C26B1.362 (6)
C16A—H16A0.9300C26A—H26A0.9300
C16B—H16B0.9300C26B—H26B0.9300
C17—H170.9300C27—H270.9300
C12—N11—C11107.6 (3)C22—N21—C21106.7 (3)
C12—N11—H11128 (3)C22—N21—H21128 (3)
C11—N11—H11124 (3)C21—N21—H21125 (3)
C12—N13—C13104.8 (3)C22—N23—C23104.4 (3)
C17—C11—N11132.0 (4)C27—C21—N21132.1 (4)
C17—C11—C13122.9 (4)C27—C21—C23122.8 (3)
N11—C11—C13105.0 (3)N21—C21—C23105.1 (3)
N13—C12—N11113.9 (4)N23—C22—N21114.5 (4)
N13—C12—H12123.0N23—C22—H22122.8
N11—C12—H12123.0N21—C22—H22122.8
C14—C13—N13131.1 (3)C24—C23—N23130.5 (4)
C14—C13—C11120.3 (4)C24—C23—C21120.1 (4)
N13—C13—C11108.6 (3)N23—C23—C21109.4 (3)
C13—C14—C15118.9 (4)C23—C24—C25118.9 (4)
C13—C14—H14120.6C23—C24—H24120.6
C15—C14—H14120.6C25—C24—H24120.6
C14—C15—C15A121.8 (4)C24—C25—C25A121.8 (4)
C14—C15—C16119.8 (4)C24—C25—C26120.4 (3)
C15A—C15—C16118.4 (4)C25A—C25—C26117.8 (4)
C15B—C15A—C15121.8 (5)C25B—C25A—C25122.0 (4)
C15B—C15A—H15A119.1C25B—C25A—H25A119.0
C15—C15A—H15A119.1C25—C25A—H25A119.0
C15A—C15B—C16B120.4 (5)C25A—C25B—C26B120.5 (4)
C15A—C15B—H15B119.8C25A—C25B—H25B119.7
C16B—C15B—H15B119.8C26B—C25B—H25B119.7
C17—C16—C15120.7 (4)C27—C26—C26A122.3 (4)
C17—C16—C16A121.5 (4)C27—C26—C25119.6 (4)
C15—C16—C16A117.8 (4)C26A—C26—C25118.1 (4)
C16B—C16A—C16121.2 (4)C26B—C26A—C26121.5 (5)
C16B—C16A—H16A119.4C26B—C26A—H26A119.2
C16—C16A—H16A119.4C26—C26A—H26A119.2
C16A—C16B—C15B120.4 (5)C26A—C26B—C25B120.1 (5)
C16A—C16B—H16B119.8C26A—C26B—H26B119.9
C15B—C16B—H16B119.8C25B—C26B—H26B119.9
C11—C17—C16117.3 (4)C21—C27—C26118.2 (4)
C11—C17—H17121.3C21—C27—H27120.9
C16—C17—H17121.4C26—C27—H27120.9
C12—N11—C11—C17179.1 (4)C22—N21—C21—C27178.4 (4)
C12—N11—C11—C130.9 (4)C22—N21—C21—C230.6 (4)
C13—N13—C12—N110.2 (4)C23—N23—C22—N210.1 (5)
C11—N11—C12—N130.7 (5)C21—N21—C22—N230.4 (5)
C12—N13—C13—C14179.9 (4)C22—N23—C23—C24177.7 (4)
C12—N13—C13—C110.4 (4)C22—N23—C23—C210.3 (4)
C17—C11—C13—C141.2 (5)C27—C21—C23—C240.8 (6)
N11—C11—C13—C14179.6 (3)N21—C21—C23—C24178.3 (4)
C17—C11—C13—N13179.2 (3)C27—C21—C23—N23178.5 (4)
N11—C11—C13—N130.8 (4)N21—C21—C23—N230.6 (4)
N13—C13—C14—C15179.9 (4)N23—C23—C24—C25177.6 (4)
C11—C13—C14—C150.6 (5)C21—C23—C24—C250.5 (6)
C13—C14—C15—C15A179.5 (4)C23—C24—C25—C25A180.0 (4)
C13—C14—C15—C160.5 (5)C23—C24—C25—C260.6 (5)
C14—C15—C15A—C15B180.0 (4)C24—C25—C25A—C25B179.8 (4)
C16—C15—C15A—C15B0.0 (6)C26—C25—C25A—C25B0.7 (6)
C15—C15A—C15B—C16B0.1 (7)C25—C25A—C25B—C26B1.4 (7)
C14—C15—C16—C171.1 (5)C24—C25—C26—C271.3 (5)
C15A—C15—C16—C17178.9 (4)C25A—C25—C26—C27179.3 (4)
C14—C15—C16—C16A179.1 (3)C24—C25—C26—C26A179.2 (4)
C15A—C15—C16—C16A0.9 (5)C25A—C25—C26—C26A0.3 (5)
C17—C16—C16A—C16B177.9 (4)C27—C26—C26A—C26B179.0 (4)
C15—C16—C16A—C16B1.8 (5)C25—C26—C26A—C26B0.6 (6)
C16—C16A—C16B—C15B1.9 (6)C26—C26A—C26B—C25B0.1 (7)
C15A—C15B—C16B—C16A1.0 (7)C25A—C25B—C26B—C26A1.1 (7)
N11—C11—C17—C16178.5 (4)N21—C21—C27—C26178.7 (4)
C13—C11—C17—C160.6 (5)C23—C21—C27—C260.1 (6)
C15—C16—C17—C110.5 (5)C26A—C26—C27—C21179.6 (4)
C16A—C16—C17—C11179.7 (4)C25—C26—C27—C210.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···N23i0.83 (5)2.12 (5)2.888 (5)155 (5)
N21—H21···N130.85 (5)2.13 (5)2.919 (5)154 (5)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
Interatomic N···C and C···C distances (Å), for molecules of type B, which lie within the range generally accepted for ππ interactions. Symmetry code: (i) x+1/2, -y, z. top
N21···C25i3.562 (6)C22···C26ai3.596 (7)
N21···C26i3.515 (6)C22···C27i3.673 (7)
N21···C27i3.734 (7)C23···C25ai3.714 (7)
N23···C26i3.752 (6)C23···C25bi3.618 (7)
N23···C26ai3.445 (7)C23···C26bi3.659 (7)
N23···C26bi3.637 (6)C24···C25bi3.523 (8)
C21···C25i3.486 (6)C27···C25i3.782 (7)
C21···C25ai3.588 (6)C27···C25ai3.655 (7)
C22···C26i3.465 (7)
Interatomic C···H distances less than 3.25 Å between an A molecule and its nearest neighbors. Symmetry codes: (i) x+1/2, y+1/2, x+1/2; (ii) x+1, y, z+1; (iii) x, -y+1/2, -1/2+z; (iv) x+1, y, z; (v) x+1, -y+1/2, z+1/2; (vi) x+1/2, -y, z; (vii) x+1/2, -y, z+1; (viii) x-1/2, -y, z; (ix) x, -y+1/2, z+1/2. top
C11···H243.10iC15a···H25a2.95vii
C11···H25b2.94iiC15b···H25a2.75vii
C11···H16a3.24iiiC16···H273.20ix
C12···H15b3.12ivC16a···H25a3.06vii
C12···H173.04iiiC16a···H26a3.15ix
C12···H26b3.22vC16a···H272.95ix
C13···H15a3.04viC16b···H25a2.81vii
C13···H16a2.90iiiC16b···H26a3.15ix
C13···H25b3.20iiC17···H243.15i
C14···H15a3.22viC17···H25b3.20ii
C15···H25a3.23viiC17···H26b3.16ii
C15a···H223.10viii
 

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