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1,2-Dimethyl-5-nitro­imidazole (dimetridazole, dimet) reacts with copper(II) chloride to give dinuclear [Cu(dimet)2(μ-Cl)Cl]2, in which each copper moiety is coordinated to two dimet ligands in a trans arrangement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016015413/lh5820sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989016015413/lh5820Isup2.hkl
Contains datablock I

CCDC reference: 1507712

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.002 Å
  • Some non-H atoms missing
  • R factor = 0.024
  • wR factor = 0.071
  • Data-to-parameter ratio = 26.2

checkCIF/PLATON results

No syntax errors found



Alert level B CHEMW03_ALERT_2_B WARNING: The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.95 <> 1.05 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_weight 915.53 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 20.00 240.22 H 1.01 28.00 28.22 N 14.01 12.00 168.08 O 16.00 8.00 127.99 Cl 35.45 4.00 141.81 Cu 63.55 2.00 127.09 Calculated formula weight 833.42
Author Response: The unit cell contains 4 acetonitrile molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. See: (a) A.L.Spek (2005) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. (b) A.L.Spek, J.Appl.Cryst. 2003, 36, 7-13.
PLAT990_ALERT_1_B Depricated RES file style based SQUEEZE job ....          ! Note
Author Response: The unit cell contains 4 acetonitrile molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. See: (a) A.L.Spek (2005) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. (b) A.L.Spek, J.Appl.Cryst. 2003, 36, 7-13.

Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H24C .. CL1 .. 2.84 Ang.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C24 H34 Cl4 Cu2 N14 O8 Atom count from the _atom_site data: C20 H28 Cl4 Cu2 N12 O8 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C24 H34 Cl4 Cu2 N14 O8 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 48.00 40.00 8.00 H 68.00 56.00 12.00 Cl 8.00 8.00 0.00 Cu 4.00 4.00 0.00 N 28.00 24.00 4.00 O 16.00 16.00 0.00 PLAT041_ALERT_1_G Calc. and Reported SumFormula Strings Differ Please Check PLAT044_ALERT_1_G Calculated and Reported Density Dx Differ by .. 0.1505 Check PLAT068_ALERT_1_G Reported F000 Differs from Calcd (or Missing)... Please Check PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Cu -- N13 .. 5.0 s.u. PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Cu -- N23 .. 5.5 s.u. PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Cu -- Cl2_a .. 15.6 s.u. PLAT605_ALERT_4_G Largest Solvent Accessible VOID in Structure ... 167 A   3 PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.12 Ratio PLAT869_ALERT_4_G ALERTS Related to the use of SQUEEZE Suppressed ! Info PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 Note PLAT933_ALERT_2_G Number of OMIT records in Embedded RES ......... 1 Note PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
0 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 15 ALERT level G = General information/check it is not something unexpected 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 5 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Di-µ-chlorido-bis[chloridobis(1,2-dimethyl-5-nitro-1H-imidazole-κN3)copper(II)] acetonitrile disolvate top
Crystal data top
[Cu2Cl4(C5H7N3O2)4]·2C2H3NF(000) = 932
Mr = 915.53Dx = 1.678 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.9545 (8) ÅCell parameters from 9452 reflections
b = 6.7004 (4) Åθ = 2.9–30.6°
c = 19.5031 (11) ŵ = 1.54 mm1
β = 96.424 (1)°T = 130 K
V = 1812.10 (18) Å3Block, blue
Z = 20.35 × 0.17 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
5034 reflections with I > 2σ(I)
φ and ω scansRint = 0.033
Absorption correction: multi-scan
(SADABS; Bruker, 2010)
θmax = 30.6°, θmin = 1.5°
Tmin = 0.637, Tmax = 0.746h = 1919
28822 measured reflectionsk = 99
5564 independent reflectionsl = 2727
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0371P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.26(Δ/σ)max = 0.033
5564 reflectionsΔρmax = 0.51 e Å3
212 parametersΔρmin = 0.51 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu0.41957 (2)0.46806 (2)0.42320 (2)0.01249 (5)
Cl10.32308 (2)0.45734 (5)0.32075 (2)0.02105 (7)
Cl20.46436 (2)0.25939 (4)0.52033 (2)0.01295 (6)
O110.10021 (7)0.39434 (18)0.58607 (6)0.0303 (2)
O120.02709 (7)0.66914 (16)0.55203 (5)0.0280 (2)
O210.81805 (7)0.13329 (16)0.33794 (5)0.0263 (2)
O220.72749 (7)0.08394 (15)0.38274 (6)0.0276 (2)
N110.09544 (8)0.55179 (17)0.55458 (6)0.0209 (2)
N120.18478 (7)0.77681 (16)0.48250 (5)0.01611 (19)
N130.30915 (7)0.58276 (15)0.46736 (5)0.01353 (18)
N210.74156 (7)0.07990 (16)0.35776 (5)0.0175 (2)
N220.65940 (7)0.39673 (15)0.31873 (5)0.01363 (18)
N230.53211 (7)0.37776 (14)0.37688 (5)0.01264 (18)
C110.17488 (8)0.59978 (19)0.51720 (6)0.0164 (2)
C120.25207 (9)0.48130 (18)0.50794 (6)0.0152 (2)
H12A0.26390.35130.52640.018*
C130.26757 (8)0.76046 (17)0.45264 (6)0.0146 (2)
C140.12067 (10)0.9527 (2)0.47787 (8)0.0247 (3)
H14A0.14801.05720.45080.037*
H14B0.11451.00300.52440.037*
H14C0.05690.91470.45540.037*
C150.30624 (9)0.92050 (19)0.41131 (7)0.0189 (2)
H15A0.35550.86500.38470.028*
H15B0.33501.02520.44220.028*
H15C0.25380.97740.37970.028*
C210.66334 (8)0.21847 (17)0.35462 (6)0.0138 (2)
C220.58485 (8)0.20765 (17)0.39040 (6)0.0135 (2)
H22A0.56960.10110.41940.016*
C230.57767 (8)0.48769 (17)0.33275 (6)0.0131 (2)
C240.72860 (10)0.4744 (2)0.27397 (7)0.0218 (3)
H24A0.75090.36530.24630.033*
H24B0.78380.53300.30240.033*
H24C0.69730.57680.24330.033*
C250.54213 (9)0.68022 (18)0.30190 (6)0.0181 (2)
H25A0.47400.69730.30850.027*
H25B0.54910.68020.25250.027*
H25C0.57980.79020.32440.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.01138 (8)0.01446 (8)0.01188 (8)0.00362 (5)0.00239 (5)0.00060 (5)
Cl10.01728 (14)0.02815 (16)0.01670 (14)0.00367 (11)0.00253 (11)0.00714 (11)
Cl20.01421 (12)0.01058 (12)0.01442 (12)0.00041 (9)0.00312 (9)0.00093 (9)
O110.0229 (5)0.0378 (6)0.0318 (6)0.0017 (4)0.0102 (4)0.0092 (5)
O120.0167 (4)0.0344 (6)0.0343 (6)0.0063 (4)0.0090 (4)0.0021 (4)
O210.0165 (4)0.0332 (5)0.0304 (5)0.0058 (4)0.0078 (4)0.0035 (4)
O220.0259 (5)0.0198 (4)0.0379 (6)0.0084 (4)0.0066 (4)0.0071 (4)
N110.0131 (5)0.0292 (6)0.0208 (5)0.0021 (4)0.0034 (4)0.0032 (4)
N120.0126 (4)0.0188 (5)0.0171 (5)0.0049 (4)0.0020 (4)0.0022 (4)
N130.0116 (4)0.0151 (4)0.0140 (4)0.0015 (3)0.0020 (3)0.0017 (3)
N210.0157 (5)0.0211 (5)0.0157 (5)0.0038 (4)0.0018 (4)0.0016 (4)
N220.0139 (4)0.0151 (4)0.0122 (4)0.0009 (4)0.0029 (3)0.0007 (3)
N230.0135 (4)0.0125 (4)0.0122 (4)0.0023 (3)0.0026 (3)0.0003 (3)
C110.0131 (5)0.0211 (6)0.0155 (5)0.0017 (4)0.0035 (4)0.0016 (4)
C120.0132 (5)0.0173 (5)0.0153 (5)0.0001 (4)0.0022 (4)0.0009 (4)
C130.0116 (5)0.0171 (5)0.0148 (5)0.0015 (4)0.0001 (4)0.0034 (4)
C140.0214 (6)0.0248 (7)0.0287 (7)0.0140 (5)0.0061 (5)0.0000 (5)
C150.0190 (6)0.0162 (5)0.0217 (6)0.0024 (4)0.0030 (5)0.0019 (4)
C210.0139 (5)0.0143 (5)0.0135 (5)0.0031 (4)0.0020 (4)0.0008 (4)
C220.0154 (5)0.0122 (5)0.0130 (5)0.0023 (4)0.0025 (4)0.0005 (4)
C230.0142 (5)0.0133 (5)0.0118 (5)0.0007 (4)0.0015 (4)0.0009 (4)
C240.0190 (6)0.0278 (7)0.0202 (6)0.0008 (5)0.0087 (5)0.0068 (5)
C250.0207 (6)0.0158 (5)0.0186 (6)0.0031 (4)0.0049 (4)0.0047 (4)
Geometric parameters (Å, º) top
Cu—N231.9914 (9)N22—C241.4678 (16)
Cu—N132.0009 (10)N23—C231.3455 (15)
Cu—Cl12.2822 (3)N23—C221.3663 (14)
Cu—Cl22.3811 (3)C11—C121.3662 (16)
Cu—Cl2i2.6024 (3)C12—H12A0.9500
Cl2—Cui2.6024 (3)C13—C151.4792 (17)
O11—N111.2188 (16)C14—H14A0.9800
O12—N111.2329 (14)C14—H14B0.9800
O12—N11ii2.9399 (15)C14—H14C0.9800
O21—N211.2285 (14)C15—H15A0.9800
O22—N211.2258 (15)C15—H15B0.9800
N11—C111.4299 (16)C15—H15C0.9800
N11—O12ii2.9399 (15)C21—C221.3649 (16)
N12—C131.3552 (15)C22—H22A0.9500
N12—C111.3802 (16)C23—C251.4850 (16)
N12—C141.4764 (15)C24—H24A0.9800
N13—C131.3414 (15)C24—H24B0.9800
N13—C121.3653 (15)C24—H24C0.9800
N21—C211.4291 (15)C25—H25A0.9800
N22—C231.3478 (15)C25—H25B0.9800
N22—C211.3823 (15)C25—H25C0.9800
N23—Cu—N13175.06 (4)N13—C12—H12A126.1
N23—Cu—Cl190.65 (3)N13—C13—N12110.42 (11)
N13—Cu—Cl188.95 (3)N13—C13—C15125.78 (11)
N23—Cu—Cl291.85 (3)N12—C13—C15123.78 (11)
N13—Cu—Cl291.68 (3)N12—C14—H14A109.5
Cl1—Cu—Cl2139.002 (12)N12—C14—H14B109.5
N23—Cu—Cl2i85.42 (3)H14A—C14—H14B109.5
N13—Cu—Cl2i91.21 (3)N12—C14—H14C109.5
Cl1—Cu—Cl2i132.139 (12)H14A—C14—H14C109.5
Cl2—Cu—Cl2i88.842 (10)H14B—C14—H14C109.5
Cu—Cl2—Cui91.158 (10)C13—C15—H15A109.5
N11—O12—N11ii95.37 (8)C13—C15—H15B109.5
O11—N11—O12124.80 (11)H15A—C15—H15B109.5
O11—N11—C11116.73 (10)C13—C15—H15C109.5
O12—N11—C11118.46 (11)H15A—C15—H15C109.5
O11—N11—O12ii85.14 (8)H15B—C15—H15C109.5
O12—N11—O12ii84.63 (8)C22—C21—N22108.42 (10)
C11—N11—O12ii100.10 (7)C22—C21—N21126.61 (11)
C13—N12—C11106.15 (10)N22—C21—N21124.75 (10)
C13—N12—C14125.32 (11)C21—C22—N23107.62 (10)
C11—N12—C14128.53 (10)C21—C22—H22A126.2
C13—N13—C12107.43 (10)N23—C22—H22A126.2
C13—N13—Cu125.75 (8)N23—C23—N22110.69 (10)
C12—N13—Cu125.84 (8)N23—C23—C25125.06 (10)
O21—N21—O22124.71 (11)N22—C23—C25124.23 (11)
O21—N21—C21118.93 (11)N22—C24—H24A109.5
O22—N21—C21116.32 (10)N22—C24—H24B109.5
C23—N22—C21105.94 (9)H24A—C24—H24B109.5
C23—N22—C24126.03 (10)N22—C24—H24C109.5
C21—N22—C24128.03 (10)H24A—C24—H24C109.5
C23—N23—C22107.29 (9)H24B—C24—H24C109.5
C23—N23—Cu125.24 (8)C23—C25—H25A109.5
C22—N23—Cu126.94 (8)C23—C25—H25B109.5
C12—C11—N12108.11 (10)H25A—C25—H25B109.5
C12—C11—N11127.19 (12)C23—C25—H25C109.5
N12—C11—N11124.69 (10)H25A—C25—H25C109.5
C11—C12—N13107.88 (11)H25B—C25—H25C109.5
C11—C12—H12A126.1
N11ii—O12—N11—O1180.27 (13)C11—N12—C13—C15178.76 (11)
N11ii—O12—N11—C1198.59 (11)C14—N12—C13—C150.78 (19)
N11ii—O12—N11—O12ii0.0C23—N22—C21—C221.06 (13)
C13—N12—C11—C120.40 (13)C24—N22—C21—C22179.19 (11)
C14—N12—C11—C12179.12 (12)C23—N22—C21—N21175.98 (11)
C13—N12—C11—N11178.29 (11)C24—N22—C21—N214.28 (19)
C14—N12—C11—N112.2 (2)O21—N21—C21—C22160.72 (12)
O11—N11—C11—C126.01 (19)O22—N21—C21—C2216.86 (18)
O12—N11—C11—C12172.94 (12)O21—N21—C21—N2213.27 (17)
O12ii—N11—C11—C1283.60 (13)O22—N21—C21—N22169.15 (11)
O11—N11—C11—N12175.55 (12)N22—C21—C22—N230.11 (13)
O12—N11—C11—N125.50 (18)N21—C21—C22—N23174.90 (11)
O12ii—N11—C11—N1294.84 (12)C23—N23—C22—C210.90 (13)
N12—C11—C12—N130.50 (13)Cu—N23—C22—C21171.07 (8)
N11—C11—C12—N13178.15 (11)C22—N23—C23—N221.62 (13)
C13—N13—C12—C110.40 (13)Cu—N23—C23—N22170.52 (7)
Cu—N13—C12—C11168.81 (8)C22—N23—C23—C25176.82 (11)
C12—N13—C13—N120.15 (13)Cu—N23—C23—C2511.04 (16)
Cu—N13—C13—N12169.07 (8)C21—N22—C23—N231.66 (13)
C12—N13—C13—C15178.42 (11)C24—N22—C23—N23178.59 (11)
Cu—N13—C13—C1512.36 (17)C21—N22—C23—C25176.79 (11)
C11—N12—C13—N130.16 (13)C24—N22—C23—C252.96 (19)
C14—N12—C13—N13179.38 (11)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25C···O22iii0.982.393.2804 (17)150
C15—H15B···Cl2iii0.982.733.6737 (13)163
C12—H12A···O22iv0.952.513.4029 (16)156
C22—H22A···Cl2iv0.952.753.6828 (12)167
C24—H24C···Cl1v0.982.843.7555 (13)156
Symmetry codes: (iii) x, y+1, z; (iv) x+1, y, z+1; (v) x+1, y+1/2, z+1/2.
 

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