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The title compound, C36H22N4, has recently been found to exhibit an excellent field effect transistor characteristic. The mol­ecule is not entirely flat in its crystal structure (i.e. not D2h) but is slightly deformed, as characterized by crystallographic Ci symmetry. The mol­ecules are stacked along the b axis in a herring-bone fashion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020750/ob6299sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020750/ob6299Isup2.hkl
Contains datablock I

CCDC reference: 225787

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.033
  • wR factor = 0.066
  • Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level A GOODF01_ALERT_2_A The least squares goodness of fit parameter lies outside the range 0.40 <> 6.00 Goodness of fit given = 0.334 PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low .... 21 Perc. PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
Alert level B PLAT086_ALERT_2_B Unsatisfactory S Value (Too Low or Not Given) .. 0.33
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.23 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 2013 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2178 Completeness (_total/calc) 92.42% RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.111 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
3 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELX86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C36H22N4F(000) = 532.0
Mr = 510.60Dx = 1.417 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ynCell parameters from 4837 reflections
a = 12.405 (1) Åθ = 3.6–68.2°
b = 6.5910 (7) ŵ = 0.66 mm1
c = 14.927 (1) ÅT = 93 K
β = 101.445 (8)°Needle, blue
V = 1196.2 (2) Å30.30 × 0.05 × 0.05 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID Imaging Plate
diffractometer
419 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.111
48 frames, δω = 15° scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1414
Tmin = 0.817, Tmax = 0.968k = 66
10724 measured reflectionsl = 1717
2013 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2)]
wR(F2) = 0.066(Δ/σ)max = 0.001
S = 0.33Δρmax = 0.07 e Å3
2013 reflectionsΔρmin = 0.11 e Å3
184 parameters
Special details top

Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.6290 (2)0.0806 (5)0.9397 (2)0.0199 (9)
N20.4101 (2)0.2622 (5)0.9471 (2)0.0192 (10)
C10.7290 (3)0.0173 (6)0.9462 (2)0.022 (1)
C20.8027 (3)0.1017 (6)0.9020 (2)0.019 (1)
C30.9115 (3)0.0771 (6)0.8910 (2)0.023 (1)
C40.9582 (3)0.2272 (6)0.8465 (2)0.024 (1)
C50.8989 (3)0.4002 (7)0.8125 (2)0.027 (1)
C60.7910 (3)0.4297 (6)0.8233 (2)0.022 (1)
C70.7451 (3)0.2757 (6)0.8675 (2)0.019 (1)
C80.6363 (3)0.2572 (6)0.8939 (2)0.023 (1)
C90.5564 (3)0.4061 (6)0.8748 (2)0.023 (1)
C100.4530 (3)0.4080 (6)0.8990 (2)0.020 (1)
C110.3708 (3)0.5677 (6)0.8775 (2)0.019 (1)
C120.3709 (3)0.7531 (6)0.8347 (2)0.027 (1)
C130.2756 (3)0.8694 (6)0.8199 (2)0.029 (1)
C140.1814 (3)0.8010 (6)0.8512 (2)0.026 (1)
C150.1831 (3)0.6200 (6)0.8987 (2)0.025 (1)
C160.2776 (3)0.5022 (6)0.9123 (2)0.022 (1)
C170.3046 (3)0.3125 (6)0.9587 (2)0.022 (1)
C180.2426 (3)0.1973 (6)1.0076 (2)0.021 (1)
H10.438 (3)0.148 (5)0.962 (2)0.0283*
H20.95260.04040.91380.0274*
H31.03180.21280.83860.0292*
H40.93290.50020.78130.0334*
H50.75060.54870.80190.0265*
H60.57380.52040.84150.0273*
H70.43510.80020.81590.0328*
H80.27390.99640.78900.0351*
H90.11610.88000.83910.0308*
H100.12060.57820.92170.0299*
H110.17140.24691.01000.0253*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.024 (2)0.015 (2)0.021 (2)0.000 (2)0.006 (1)0.001 (2)
N20.021 (2)0.014 (2)0.023 (2)0.009 (2)0.006 (1)0.003 (2)
C10.027 (2)0.021 (3)0.016 (2)0.001 (2)0.004 (2)0.003 (2)
C20.024 (2)0.017 (3)0.017 (2)0.007 (2)0.005 (2)0.000 (2)
C30.025 (2)0.017 (3)0.029 (2)0.009 (2)0.011 (2)0.000 (2)
C40.018 (2)0.034 (3)0.023 (2)0.003 (2)0.009 (2)0.001 (2)
C50.021 (2)0.034 (3)0.028 (2)0.001 (2)0.009 (2)0.009 (2)
C60.025 (2)0.019 (3)0.022 (2)0.002 (2)0.001 (2)0.002 (2)
C70.019 (2)0.022 (3)0.016 (2)0.001 (2)0.004 (2)0.004 (2)
C80.030 (2)0.021 (3)0.017 (2)0.000 (2)0.004 (2)0.001 (2)
C90.028 (2)0.019 (3)0.023 (2)0.009 (2)0.006 (2)0.001 (2)
C100.027 (2)0.012 (3)0.022 (2)0.005 (2)0.005 (2)0.001 (2)
C110.021 (2)0.017 (3)0.020 (2)0.002 (2)0.006 (2)0.008 (2)
C120.034 (2)0.030 (3)0.018 (2)0.007 (3)0.009 (2)0.002 (2)
C130.038 (2)0.025 (3)0.024 (2)0.002 (2)0.002 (2)0.003 (2)
C140.027 (2)0.031 (3)0.020 (2)0.005 (2)0.002 (2)0.001 (2)
C150.023 (2)0.028 (3)0.023 (2)0.001 (2)0.006 (2)0.006 (2)
C160.032 (2)0.018 (3)0.013 (2)0.001 (2)0.001 (2)0.000 (2)
C170.021 (2)0.025 (3)0.017 (2)0.001 (2)0.002 (2)0.004 (2)
C180.019 (2)0.019 (3)0.023 (2)0.006 (2)0.003 (2)0.004 (2)
Geometric parameters (Å, º) top
N1—C11.384 (4)C8—C91.384 (5)
N1—C81.362 (4)C9—C101.400 (4)
N2—C101.369 (4)C9—H60.951
N2—C171.394 (4)C10—C111.457 (5)
N2—H10.84 (3)C11—C121.379 (5)
C1—C21.458 (5)C11—C161.424 (5)
C1—C18i1.382 (5)C12—C131.390 (5)
C2—C31.401 (5)C12—H70.948
C2—C71.394 (5)C13—C141.415 (5)
C3—C41.382 (5)C13—H80.953
C3—H20.952C14—C151.386 (5)
C4—C51.397 (5)C14—H90.950
C4—H30.948C15—C161.388 (5)
C5—C61.393 (5)C15—H100.949
C5—H40.952C16—C171.436 (4)
C6—C71.393 (5)C17—C181.386 (4)
C6—H50.951C18—H110.950
C7—C81.483 (4)
N1···C12ii3.541 (4)C8···C16ii3.287 (5)
N1···C13ii3.564 (4)C8···C15ii3.537 (5)
N1···C16ii3.574 (5)C8···C17ii3.576 (5)
N1···C11ii3.581 (4)C9···C17ii3.300 (5)
N1···C15ii3.594 (4)C9···C16ii3.480 (5)
N2···C10ii3.368 (5)C10···C10ii3.246 (7)
N2···C9ii3.403 (5)C11···C13v3.400 (5)
N2···C13iii3.440 (5)C11···H1ii3.56 (3)
N2···C11ii3.561 (4)C12···H1vi3.23 (3)
C1···C14ii3.329 (5)C12···H1ii3.52 (3)
C1···C15ii3.522 (5)C13···H1vi3.20 (3)
C2···C15ii3.469 (5)C13···C16vii3.507 (5)
C2···C6iv3.520 (5)C13···C17vi3.557 (5)
C7···C15ii3.494 (5)C14···C18vi3.485 (5)
C1—N1—C8106.6 (3)C8—C9—H6116.2
C10—N2—C17111.7 (3)C10—C9—H6116.3
C10—N2—H1126 (2)N2—C10—C9126.9 (4)
C17—N2—H1121 (2)N2—C10—C11107.1 (3)
N1—C1—C2110.5 (3)C9—C10—C11126.0 (4)
N1—C1—C18i124.8 (4)C10—C11—C12132.6 (4)
C2—C1—C18i124.6 (4)C10—C11—C16106.5 (3)
C1—C2—C3134.1 (4)C12—C11—C16120.9 (4)
C1—C2—C7106.7 (3)C11—C12—C13118.9 (3)
C3—C2—C7119.1 (4)C11—C12—H7120.4
C2—C3—C4118.7 (4)C13—C12—H7120.7
C2—C3—H2120.8C12—C13—C14120.2 (4)
C4—C3—H2120.5C12—C13—H8119.9
C3—C4—C5121.2 (3)C14—C13—H8119.9
C3—C4—H3119.6C13—C14—C15121.0 (4)
C5—C4—H3119.1C13—C14—H9119.5
C4—C5—C6121.4 (4)C15—C14—H9119.6
C4—C5—H4119.4C14—C15—C16118.8 (4)
C6—C5—H4119.3C14—C15—H10120.4
C5—C6—C7116.5 (4)C16—C15—H10120.8
C5—C6—H5122.0C11—C16—C15120.0 (4)
C7—C6—H5121.5C11—C16—C17108.2 (3)
C2—C7—C6123.1 (3)C15—C16—C17131.8 (4)
C2—C7—C8105.1 (3)N2—C17—C16106.3 (3)
C6—C7—C8131.7 (4)N2—C17—C18124.6 (4)
N1—C8—C7111.0 (4)C16—C17—C18129.1 (4)
N1—C8—C9126.4 (3)C1i—C18—C17128.3 (3)
C7—C8—C9122.6 (4)C1i—C18—H11115.0
C8—C9—C10127.5 (4)C17—C18—H11116.6
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y+1, z+2; (iii) x, y1, z; (iv) x+3/2, y1/2, z+3/2; (v) x+1/2, y1/2, z+3/2; (vi) x, y+1, z; (vii) x+1/2, y+1/2, z+3/2.
 

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