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In the title compound, C7H8N4, the C atom of the bridging methyl­ene group lies on a twofold rotation axis. The dihedral angle between the symmetry-related imidazole rings is 75.0 (2)°. The crystal packing is stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011512/cv2026sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011512/cv2026Isup2.hkl
Contains datablock I

CCDC reference: 608590

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.123
  • Data-to-parameter ratio = 9.8

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: 0.757 0.998 Tmin(prime) and Tmax expected: 0.956 0.972 RR(prime) = 0.771 Please check that your absorption correction is appropriate. PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.75 Sigma PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.77 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.17 Ratio
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 27.00 From the CIF: _reflns_number_total 508 Count of symmetry unique reflns 508 Completeness (_total/calc) 100.00% 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 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Bis(imidazol-1-yl)methane top
Crystal data top
C7H8N4Dx = 1.332 Mg m3
Mr = 148.17Melting point = 429–431 K
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
a = 8.0357 (18) ÅCell parameters from 1241 reflections
b = 10.545 (2) Åθ = 6.4–53.0°
c = 4.3613 (10) ŵ = 0.09 mm1
V = 369.55 (15) Å3T = 293 K
Z = 2Block, colourless
F(000) = 1560.49 × 0.45 × 0.32 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
508 independent reflections
Radiation source: fine-focus sealed tube461 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
φ and ω scansθmax = 27.0°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 107
Tmin = 0.757, Tmax = 0.998k = 1313
2176 measured reflectionsl = 55
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)] = 0.048H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0898P)2 + 0.003P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.007
508 reflectionsΔρmax = 0.19 e Å3
52 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.11 (4)
Special details top

Experimental. 1H NMR (300 MHz, CDCl3): δ 6.87 (2H, s), 6.77 (2H, s), 5.77 (2H, s); 13C NMR: δ 144.8, 128.9, 119.1, 55.7. It was crystallized by slow evaporation of a chloroform–methanol (5:1 v/v) mixture (yield 200 mg, 78%; m.p. 441–442 K)

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
N10.2438 (2)0.27007 (13)0.3079 (5)0.0676 (7)
N20.11821 (17)0.43083 (13)0.0844 (4)0.0432 (5)
C10.1230 (2)0.30409 (17)0.1293 (6)0.0581 (6)
H1A0.04800.24760.04180.070*
C20.3227 (3)0.38050 (16)0.3841 (6)0.0586 (6)
H2A0.41510.38590.51180.070*
C30.2487 (2)0.48015 (14)0.2497 (4)0.0535 (6)
H3A0.27940.56500.26520.064*
C40.00000.50000.1006 (7)0.0512 (7)
H4A0.05940.55900.23150.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0609 (10)0.0453 (10)0.0966 (15)0.0108 (8)0.0019 (10)0.0085 (9)
N20.0378 (7)0.0373 (8)0.0544 (8)0.0037 (6)0.0042 (6)0.0022 (7)
C10.0563 (11)0.0360 (9)0.0820 (13)0.0020 (8)0.0003 (12)0.0038 (9)
C20.0429 (9)0.0606 (11)0.0723 (12)0.0085 (8)0.0020 (10)0.0009 (11)
C30.0416 (9)0.0442 (10)0.0747 (11)0.0034 (7)0.0026 (10)0.0022 (9)
C40.0489 (13)0.0548 (14)0.0500 (12)0.0096 (11)0.0000.000
Geometric parameters (Å, º) top
N1—C11.295 (3)C2—C31.342 (2)
N1—C21.367 (2)C2—H2A0.9300
N2—C11.351 (2)C3—H3A0.9300
N2—C31.375 (2)C4—N2i1.444 (2)
N2—C41.444 (2)C4—H4A0.9700
C1—H1A0.9300C4—H4Ai0.9700
C1—N1—C2104.94 (16)C3—C2—H2A124.6
C1—N2—C3106.04 (16)N1—C2—H2A124.6
C1—N2—C4126.83 (14)C2—C3—N2105.71 (14)
C3—N2—C4127.13 (13)C2—C3—H3A127.1
N1—C1—N2112.50 (18)N2—C3—H3A127.1
N1—C1—H1A123.8N2i—C4—N2112.1 (2)
N2—C1—H1A123.8N2i—C4—H4A109.2
C3—C2—N1110.81 (19)N2—C4—H4A109.2
C2—N1—C1—N20.1 (2)C1—N2—C3—C20.3 (2)
C3—N2—C1—N10.3 (2)C4—N2—C3—C2179.8 (2)
C4—N2—C1—N1179.90 (19)C1—N2—C4—N2i106.63 (19)
C1—N1—C2—C30.1 (2)C3—N2—C4—N2i73.57 (15)
N1—C2—C3—N20.3 (2)
Symmetry code: (i) x, y+1, z.
 

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