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p-Diiso­cyano­tetra­methyl­benzene, p-C6(CH3)4(NC)2, crystallizes in the monoclinic space group C2/c. One-half of the mol­ecule is crystallographically independent, with the other half being generated by an inversion centre located at the centre of the mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020087/fl6059sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020087/fl6059Isup2.hkl
Contains datablock I

CCDC reference: 226955

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.046
  • wR factor = 0.131
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.75 Sigma PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C2 = 5.53 su PLAT320_ALERT_2_C Check Hybridisation of C1 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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 1997-2000); cell refinement: SAINT-Plus (Bruker 1997-1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97.

1,4-bisisocyano-2,3,5,6-tetramethyl benzene top
Crystal data top
C12H12N2F(000) = 392
Mr = 184.24Dx = 1.221 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 17.1518 (17) ÅCell parameters from 4202 reflections
b = 5.1324 (5) Åθ = 2.6–28.3°
c = 12.3670 (12) ŵ = 0.07 mm1
β = 112.010 (2)°T = 100 K
V = 1009.32 (17) Å3Block, colourless
Z = 40.5 × 0.35 × 0.35 mm
Data collection top
Bruker AXS SMART APEX CCD
diffractometer
1181 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.080
Graphite monochromatorθmax = 28.3°, θmin = 3.5°
ω scansh = 2221
4935 measured reflectionsk = 66
1257 independent reflectionsl = 1616
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) = 0.131 w = 1/[σ2(Fo2) + (0.0698P)2 + 0.6662P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.016
1257 reflectionsΔρmax = 0.32 e Å3
69 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (4)
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*/UeqOcc. (<1)
N10.35731 (5)1.04662 (17)0.68084 (7)0.0217 (3)
C30.33877 (6)0.71435 (19)0.53560 (8)0.0190 (3)
C40.28404 (6)0.56146 (19)0.44509 (8)0.0189 (3)
C10.40179 (7)1.1675 (2)0.75919 (9)0.0288 (3)
C20.30288 (6)0.89616 (19)0.58851 (8)0.0188 (3)
C50.43300 (6)0.6884 (2)0.57347 (9)0.0245 (3)
H5A0.46050.83400.62490.037*0.899 (16)
H5B0.44830.69060.50470.037*0.899 (16)
H5C0.45130.52370.61550.037*0.899 (16)
H5D0.44620.53150.53850.037*0.101 (16)
H5E0.45850.67490.65870.037*0.101 (16)
H5F0.45550.84180.54790.037*0.101 (16)
C60.31677 (6)0.3562 (2)0.38534 (9)0.0242 (3)
H6A0.27400.22070.35330.036*0.721 (16)
H6B0.36800.27820.44190.036*0.721 (16)
H6C0.32960.43650.32200.036*0.721 (16)
H6D0.37370.40290.39150.036*0.279 (16)
H6E0.27970.34540.30290.036*0.279 (16)
H6F0.31810.18720.42280.036*0.279 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0224 (4)0.0249 (5)0.0205 (4)0.0007 (3)0.0111 (3)0.0005 (3)
C30.0198 (5)0.0224 (5)0.0175 (4)0.0016 (3)0.0100 (4)0.0030 (3)
C40.0220 (5)0.0204 (5)0.0179 (5)0.0014 (3)0.0114 (4)0.0018 (3)
C10.0261 (5)0.0349 (6)0.0265 (5)0.0015 (4)0.0110 (4)0.0056 (4)
C20.0211 (5)0.0212 (5)0.0160 (4)0.0010 (3)0.0091 (3)0.0006 (3)
C50.0193 (5)0.0319 (6)0.0237 (5)0.0022 (4)0.0096 (4)0.0003 (4)
C60.0277 (5)0.0248 (5)0.0257 (5)0.0021 (4)0.0163 (4)0.0022 (4)
Geometric parameters (Å, º) top
N1—C11.1628 (14)C5—H5D0.9800
N1—C21.4045 (12)C5—H5E0.9800
C3—C41.4008 (13)C5—H5F0.9800
C3—C21.4070 (13)C6—H6A0.9800
C3—C51.5106 (13)C6—H6B0.9800
C4—C61.5105 (13)C6—H6C0.9800
C2—C4i1.4065 (13)C6—H6D0.9800
C5—H5A0.9800C6—H6E0.9800
C5—H5B0.9800C6—H6F0.9800
C5—H5C0.9800
C1—N1—C2178.30 (10)H5A—C5—H5F56.3
C4—C3—C2117.65 (9)H5B—C5—H5F56.3
C4—C3—C5121.14 (8)H5C—C5—H5F141.1
C2—C3—C5121.20 (9)H5D—C5—H5F109.5
C3—C4—C2i117.92 (9)H5E—C5—H5F109.5
C3—C4—C6121.39 (8)C4—C6—H6A109.5
C2i—C4—C6120.69 (9)C4—C6—H6B109.5
N1—C2—C4i117.59 (8)H6A—C6—H6B109.5
N1—C2—C3117.99 (8)C4—C6—H6C109.5
C4i—C2—C3124.42 (9)H6A—C6—H6C109.5
C3—C5—H5A109.5H6B—C6—H6C109.5
C3—C5—H5B109.5C4—C6—H6D109.5
H5A—C5—H5B109.5H6A—C6—H6D141.1
C3—C5—H5C109.5H6B—C6—H6D56.3
H5A—C5—H5C109.5H6C—C6—H6D56.3
H5B—C5—H5C109.5C4—C6—H6E109.5
C3—C5—H5D109.5H6A—C6—H6E56.3
H5A—C5—H5D141.1H6B—C6—H6E141.1
H5B—C5—H5D56.3H6C—C6—H6E56.3
H5C—C5—H5D56.3H6D—C6—H6E109.5
C3—C5—H5E109.5C4—C6—H6F109.5
H5A—C5—H5E56.3H6A—C6—H6F56.3
H5B—C5—H5E141.1H6B—C6—H6F56.3
H5C—C5—H5E56.3H6C—C6—H6F141.1
H5D—C5—H5E109.5H6D—C6—H6F109.5
C3—C5—H5F109.5H6E—C6—H6F109.5
C2—C3—C4—C2i1.38 (15)C4—C3—C2—N1178.78 (8)
C5—C3—C4—C2i177.49 (8)C5—C3—C2—N12.35 (14)
C2—C3—C4—C6178.34 (8)C4—C3—C2—C4i1.48 (16)
C5—C3—C4—C62.79 (14)C5—C3—C2—C4i177.39 (9)
Symmetry code: (i) x+1/2, y+3/2, z+1.
 

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