Crystal structure of di-μ-chlorido-bis­[chlorido­bis­(1,2-dimethyl-5-nitro-1H-imidazole-κN3)copper(II)] acetonitrile disolvate

Quinlivan, P.J.; Upmacis, R.K.

doi:10.1107/S2056989016015413

Crystal structure of di-μ-chlorido-bis[chloridobis(1,2-dimethyl-5-nitro-1H-imidazole-κN³)copper(II)] acetonitrile disolvate

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.

Keywords: crystal structure; copper(II); chloride-bridged dimer; dimetridazole; dimet.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016015413/lh5820sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989016015413/lh5820Isup2.hkl Contains datablock I

CCDC reference: 1507712

checkCIF report

Key indicators

Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.002 Å
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


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]·2C₂H₃N	F(000) = 932
M_r = 915.53	D_x = 1.678 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.9545 (8) Å	Cell parameters from 9452 reflections
b = 6.7004 (4) Å	θ = 2.9–30.6°
c = 19.5031 (11) Å	µ = 1.54 mm⁻¹
β = 96.424 (1)°	T = 130 K
V = 1812.10 (18) Å³	Block, blue
Z = 2	0.35 × 0.17 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	5034 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.033
Absorption correction: multi-scan (SADABS; Bruker, 2010)	θ_max = 30.6°, θ_min = 1.5°
T_min = 0.637, T_max = 0.746	h = −19→19
28822 measured reflections	k = −9→9
5564 independent reflections	l = −27→27

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.071	w = 1/[σ²(F_o²) + (0.0371P)²] where P = (F_o² + 2F_c²)/3
S = 1.26	(Δ/σ)_max = 0.033
5564 reflections	Δρ_max = 0.51 e Å⁻³
212 parameters	Δρ_min = −0.51 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Cu	0.41957 (2)	0.46806 (2)	0.42320 (2)	0.01249 (5)
Cl1	0.32308 (2)	0.45734 (5)	0.32075 (2)	0.02105 (7)
Cl2	0.46436 (2)	0.25939 (4)	0.52033 (2)	0.01295 (6)
O11	0.10021 (7)	0.39434 (18)	0.58607 (6)	0.0303 (2)
O12	0.02709 (7)	0.66914 (16)	0.55203 (5)	0.0280 (2)
O21	0.81805 (7)	0.13329 (16)	0.33794 (5)	0.0263 (2)
O22	0.72749 (7)	−0.08394 (15)	0.38274 (6)	0.0276 (2)
N11	0.09544 (8)	0.55179 (17)	0.55458 (6)	0.0209 (2)
N12	0.18478 (7)	0.77681 (16)	0.48250 (5)	0.01611 (19)
N13	0.30915 (7)	0.58276 (15)	0.46736 (5)	0.01353 (18)
N21	0.74156 (7)	0.07990 (16)	0.35776 (5)	0.0175 (2)
N22	0.65940 (7)	0.39673 (15)	0.31873 (5)	0.01363 (18)
N23	0.53211 (7)	0.37776 (14)	0.37688 (5)	0.01264 (18)
C11	0.17488 (8)	0.59978 (19)	0.51720 (6)	0.0164 (2)
C12	0.25207 (9)	0.48130 (18)	0.50794 (6)	0.0152 (2)
H12A	0.2639	0.3513	0.5264	0.018*
C13	0.26757 (8)	0.76046 (17)	0.45264 (6)	0.0146 (2)
C14	0.12067 (10)	0.9527 (2)	0.47787 (8)	0.0247 (3)
H14A	0.1480	1.0572	0.4508	0.037*
H14B	0.1145	1.0030	0.5244	0.037*
H14C	0.0569	0.9147	0.4554	0.037*
C15	0.30624 (9)	0.92050 (19)	0.41131 (7)	0.0189 (2)
H15A	0.3555	0.8650	0.3847	0.028*
H15B	0.3350	1.0252	0.4422	0.028*
H15C	0.2538	0.9774	0.3797	0.028*
C21	0.66334 (8)	0.21847 (17)	0.35462 (6)	0.0138 (2)
C22	0.58485 (8)	0.20765 (17)	0.39040 (6)	0.0135 (2)
H22A	0.5696	0.1011	0.4194	0.016*
C23	0.57767 (8)	0.48769 (17)	0.33275 (6)	0.0131 (2)
C24	0.72860 (10)	0.4744 (2)	0.27397 (7)	0.0218 (3)
H24A	0.7509	0.3653	0.2463	0.033*
H24B	0.7838	0.5330	0.3024	0.033*
H24C	0.6973	0.5768	0.2433	0.033*
C25	0.54213 (9)	0.68022 (18)	0.30190 (6)	0.0181 (2)
H25A	0.4740	0.6973	0.3085	0.027*
H25B	0.5491	0.6802	0.2525	0.027*
H25C	0.5798	0.7902	0.3244	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.01138 (8)	0.01446 (8)	0.01188 (8)	0.00362 (5)	0.00239 (5)	−0.00060 (5)
Cl1	0.01728 (14)	0.02815 (16)	0.01670 (14)	0.00367 (11)	−0.00253 (11)	−0.00714 (11)
Cl2	0.01421 (12)	0.01058 (12)	0.01442 (12)	0.00041 (9)	0.00312 (9)	0.00093 (9)
O11	0.0229 (5)	0.0378 (6)	0.0318 (6)	0.0017 (4)	0.0102 (4)	0.0092 (5)
O12	0.0167 (4)	0.0344 (6)	0.0343 (6)	0.0063 (4)	0.0090 (4)	−0.0021 (4)
O21	0.0165 (4)	0.0332 (5)	0.0304 (5)	0.0058 (4)	0.0078 (4)	0.0035 (4)
O22	0.0259 (5)	0.0198 (4)	0.0379 (6)	0.0084 (4)	0.0066 (4)	0.0071 (4)
N11	0.0131 (5)	0.0292 (6)	0.0208 (5)	0.0021 (4)	0.0034 (4)	−0.0032 (4)
N12	0.0126 (4)	0.0188 (5)	0.0171 (5)	0.0049 (4)	0.0020 (4)	−0.0022 (4)
N13	0.0116 (4)	0.0151 (4)	0.0140 (4)	0.0015 (3)	0.0020 (3)	−0.0017 (3)
N21	0.0157 (5)	0.0211 (5)	0.0157 (5)	0.0038 (4)	0.0018 (4)	−0.0016 (4)
N22	0.0139 (4)	0.0151 (4)	0.0122 (4)	0.0009 (4)	0.0029 (3)	0.0007 (3)
N23	0.0135 (4)	0.0125 (4)	0.0122 (4)	0.0023 (3)	0.0026 (3)	0.0003 (3)
C11	0.0131 (5)	0.0211 (6)	0.0155 (5)	0.0017 (4)	0.0035 (4)	−0.0016 (4)
C12	0.0132 (5)	0.0173 (5)	0.0153 (5)	0.0001 (4)	0.0022 (4)	−0.0009 (4)
C13	0.0116 (5)	0.0171 (5)	0.0148 (5)	0.0015 (4)	0.0001 (4)	−0.0034 (4)
C14	0.0214 (6)	0.0248 (7)	0.0287 (7)	0.0140 (5)	0.0061 (5)	0.0000 (5)
C15	0.0190 (6)	0.0162 (5)	0.0217 (6)	0.0024 (4)	0.0030 (5)	0.0019 (4)
C21	0.0139 (5)	0.0143 (5)	0.0135 (5)	0.0031 (4)	0.0020 (4)	−0.0008 (4)
C22	0.0154 (5)	0.0122 (5)	0.0130 (5)	0.0023 (4)	0.0025 (4)	0.0005 (4)
C23	0.0142 (5)	0.0133 (5)	0.0118 (5)	0.0007 (4)	0.0015 (4)	−0.0009 (4)
C24	0.0190 (6)	0.0278 (7)	0.0202 (6)	0.0008 (5)	0.0087 (5)	0.0068 (5)
C25	0.0207 (6)	0.0158 (5)	0.0186 (6)	0.0031 (4)	0.0049 (4)	0.0047 (4)

Geometric parameters (Å, º) top

Cu—N23	1.9914 (9)	N22—C24	1.4678 (16)
Cu—N13	2.0009 (10)	N23—C23	1.3455 (15)
Cu—Cl1	2.2822 (3)	N23—C22	1.3663 (14)
Cu—Cl2	2.3811 (3)	C11—C12	1.3662 (16)
Cu—Cl2ⁱ	2.6024 (3)	C12—H12A	0.9500
Cl2—Cuⁱ	2.6024 (3)	C13—C15	1.4792 (17)
O11—N11	1.2188 (16)	C14—H14A	0.9800
O12—N11	1.2329 (14)	C14—H14B	0.9800
O12—N11ⁱⁱ	2.9399 (15)	C14—H14C	0.9800
O21—N21	1.2285 (14)	C15—H15A	0.9800
O22—N21	1.2258 (15)	C15—H15B	0.9800
N11—C11	1.4299 (16)	C15—H15C	0.9800
N11—O12ⁱⁱ	2.9399 (15)	C21—C22	1.3649 (16)
N12—C13	1.3552 (15)	C22—H22A	0.9500
N12—C11	1.3802 (16)	C23—C25	1.4850 (16)
N12—C14	1.4764 (15)	C24—H24A	0.9800
N13—C13	1.3414 (15)	C24—H24B	0.9800
N13—C12	1.3653 (15)	C24—H24C	0.9800
N21—C21	1.4291 (15)	C25—H25A	0.9800
N22—C23	1.3478 (15)	C25—H25B	0.9800
N22—C21	1.3823 (15)	C25—H25C	0.9800

N23—Cu—N13	175.06 (4)	N13—C12—H12A	126.1
N23—Cu—Cl1	90.65 (3)	N13—C13—N12	110.42 (11)
N13—Cu—Cl1	88.95 (3)	N13—C13—C15	125.78 (11)
N23—Cu—Cl2	91.85 (3)	N12—C13—C15	123.78 (11)
N13—Cu—Cl2	91.68 (3)	N12—C14—H14A	109.5
Cl1—Cu—Cl2	139.002 (12)	N12—C14—H14B	109.5
N23—Cu—Cl2ⁱ	85.42 (3)	H14A—C14—H14B	109.5
N13—Cu—Cl2ⁱ	91.21 (3)	N12—C14—H14C	109.5
Cl1—Cu—Cl2ⁱ	132.139 (12)	H14A—C14—H14C	109.5
Cl2—Cu—Cl2ⁱ	88.842 (10)	H14B—C14—H14C	109.5
Cu—Cl2—Cuⁱ	91.158 (10)	C13—C15—H15A	109.5
N11—O12—N11ⁱⁱ	95.37 (8)	C13—C15—H15B	109.5
O11—N11—O12	124.80 (11)	H15A—C15—H15B	109.5
O11—N11—C11	116.73 (10)	C13—C15—H15C	109.5
O12—N11—C11	118.46 (11)	H15A—C15—H15C	109.5
O11—N11—O12ⁱⁱ	85.14 (8)	H15B—C15—H15C	109.5
O12—N11—O12ⁱⁱ	84.63 (8)	C22—C21—N22	108.42 (10)
C11—N11—O12ⁱⁱ	100.10 (7)	C22—C21—N21	126.61 (11)
C13—N12—C11	106.15 (10)	N22—C21—N21	124.75 (10)
C13—N12—C14	125.32 (11)	C21—C22—N23	107.62 (10)
C11—N12—C14	128.53 (10)	C21—C22—H22A	126.2
C13—N13—C12	107.43 (10)	N23—C22—H22A	126.2
C13—N13—Cu	125.75 (8)	N23—C23—N22	110.69 (10)
C12—N13—Cu	125.84 (8)	N23—C23—C25	125.06 (10)
O21—N21—O22	124.71 (11)	N22—C23—C25	124.23 (11)
O21—N21—C21	118.93 (11)	N22—C24—H24A	109.5
O22—N21—C21	116.32 (10)	N22—C24—H24B	109.5
C23—N22—C21	105.94 (9)	H24A—C24—H24B	109.5
C23—N22—C24	126.03 (10)	N22—C24—H24C	109.5
C21—N22—C24	128.03 (10)	H24A—C24—H24C	109.5
C23—N23—C22	107.29 (9)	H24B—C24—H24C	109.5
C23—N23—Cu	125.24 (8)	C23—C25—H25A	109.5
C22—N23—Cu	126.94 (8)	C23—C25—H25B	109.5
C12—C11—N12	108.11 (10)	H25A—C25—H25B	109.5
C12—C11—N11	127.19 (12)	C23—C25—H25C	109.5
N12—C11—N11	124.69 (10)	H25A—C25—H25C	109.5
C11—C12—N13	107.88 (11)	H25B—C25—H25C	109.5
C11—C12—H12A	126.1

N11ⁱⁱ—O12—N11—O11	−80.27 (13)	C11—N12—C13—C15	−178.76 (11)
N11ⁱⁱ—O12—N11—C11	98.59 (11)	C14—N12—C13—C15	0.78 (19)
N11ⁱⁱ—O12—N11—O12ⁱⁱ	0.0	C23—N22—C21—C22	−1.06 (13)
C13—N12—C11—C12	0.40 (13)	C24—N22—C21—C22	179.19 (11)
C14—N12—C11—C12	−179.12 (12)	C23—N22—C21—N21	−175.98 (11)
C13—N12—C11—N11	−178.29 (11)	C24—N22—C21—N21	4.28 (19)
C14—N12—C11—N11	2.2 (2)	O21—N21—C21—C22	−160.72 (12)
O11—N11—C11—C12	6.01 (19)	O22—N21—C21—C22	16.86 (18)
O12—N11—C11—C12	−172.94 (12)	O21—N21—C21—N22	13.27 (17)
O12ⁱⁱ—N11—C11—C12	−83.60 (13)	O22—N21—C21—N22	−169.15 (11)
O11—N11—C11—N12	−175.55 (12)	N22—C21—C22—N23	0.11 (13)
O12—N11—C11—N12	5.50 (18)	N21—C21—C22—N23	174.90 (11)
O12ⁱⁱ—N11—C11—N12	94.84 (12)	C23—N23—C22—C21	0.90 (13)
N12—C11—C12—N13	−0.50 (13)	Cu—N23—C22—C21	−171.07 (8)
N11—C11—C12—N13	178.15 (11)	C22—N23—C23—N22	−1.62 (13)
C13—N13—C12—C11	0.40 (13)	Cu—N23—C23—N22	170.52 (7)
Cu—N13—C12—C11	−168.81 (8)	C22—N23—C23—C25	176.82 (11)
C12—N13—C13—N12	−0.15 (13)	Cu—N23—C23—C25	−11.04 (16)
Cu—N13—C13—N12	169.07 (8)	C21—N22—C23—N23	1.66 (13)
C12—N13—C13—C15	178.42 (11)	C24—N22—C23—N23	−178.59 (11)
Cu—N13—C13—C15	−12.36 (17)	C21—N22—C23—C25	−176.79 (11)
C11—N12—C13—N13	−0.16 (13)	C24—N22—C23—C25	2.96 (19)
C14—N12—C13—N13	179.38 (11)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25C···O22ⁱⁱⁱ	0.98	2.39	3.2804 (17)	150
C15—H15B···Cl2ⁱⁱⁱ	0.98	2.73	3.6737 (13)	163
C12—H12A···O22^iv	0.95	2.51	3.4029 (16)	156
C22—H22A···Cl2^iv	0.95	2.75	3.6828 (12)	167
C24—H24C···Cl1^v	0.98	2.84	3.7555 (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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Crystal structure of di-μ-chlorido-bis­[chlorido­bis­(1,2-dimethyl-5-nitro-1H-imidazole-κN3)copper(II)] acetonitrile disolvate

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of di-μ-chlorido-bis[chloridobis(1,2-dimethyl-5-nitro-1H-imidazole-κN³)copper(II)] acetonitrile disolvate