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In the title compound, (2-amino-4,6-di­methyl­pyridinium) ­di­iodo­cuprate(I), (C7H11N2)[CuI2], the planar 2-amino-4,6-di­methyl­pyridine species is protonated at the pyridine N atom. It interacts with the inorganic chains by extensive hydrogen bonding. The cation forms N—H...I hydrogen bonds from both its pyridine and amine N atoms. The copper(I) species is tetrahedrally bonded to four iodide ions (average Cu—I distance = 2.665 Å, with a standard uncertainty of 0.019 Å) and forms infinite edge-sharing chains. Atom-site symmetries: Cu (2); I, phenyl-C and N (m).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027715/hb6003sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027715/hb6003Isup2.hkl
Contains datablock I

CCDC reference: 231825

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.028
  • wR factor = 0.075
  • Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.86 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C6 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C7 PLAT764_ALERT_4_C Overcomplete CIF Bond list Detected (Rep/Expd) . 1.54 Ratio
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 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1996); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(2-Amino-4,6-dimethylpyridinium)diiodocopper(I) top
Crystal data top
[CuI2(C7H11N2)]F(000) = 808
Mr = 440.52Dx = 2.509 Mg m3
Monoclinic, C2/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yCell parameters from 4476 reflections
a = 19.003 (4) Åθ = 2.2–30.0°
b = 6.7188 (13) ŵ = 7.16 mm1
c = 9.2156 (18) ÅT = 296 K
β = 99.37 (3)°Plate, colourless
V = 1160.9 (4) Å30.44 × 0.31 × 0.05 mm
Z = 4
Data collection top
Bruker/Siemens SMART APEX CCD
diffractometer
1434 independent reflections
Radiation source: fine-focus sealed tube1316 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 8.3 pixels mm-1θmax = 27.5°, θmin = 2.2°
ω scansh = 2424
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
k = 88
Tmin = 0.070, Tmax = 0.697l = 1111
7083 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0385P)2 + 1.2949P]
where P = (Fo2 + 2Fc2)/3
1434 reflections(Δ/σ)max < 0.001
72 parametersΔρmax = 1.08 e Å3
0 restraintsΔρmin = 0.38 e Å3
Special details top

Experimental. Crystals were sensitive to exposure to the atmosphere, They become very dark and decompose if touched by paper or if get wet. They were kept wet with some mother liquor but no special precaution was take during data collection.

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
C50.3372 (3)0.50000.3384 (6)0.0482 (11)
C40.2845 (3)0.50000.4248 (7)0.0530 (12)
H40.29670.50000.52670.064*
C30.2119 (3)0.50000.3586 (7)0.0512 (12)
C20.1959 (3)0.50000.2084 (7)0.0513 (12)
H20.14840.50000.16360.062*
C10.2483 (3)0.50000.1230 (7)0.0585 (13)
C60.1533 (3)0.50000.4500 (9)0.0710 (17)
H6A0.10790.50000.38610.106*
H6B0.15720.38330.51050.106*
C70.4152 (3)0.50000.3995 (7)0.0596 (14)
H7A0.44240.50000.32040.089*
H7B0.42690.61670.45910.089*
Cu0.00000.25861 (11)0.00000.0642 (2)
I10.049357 (18)0.50000.18719 (4)0.05131 (13)
I20.093627 (17)0.00000.14488 (4)0.05218 (13)
N10.3179 (2)0.50000.1907 (5)0.0548 (11)
H10.35090.50000.13690.066*
N20.2348 (3)0.50000.0244 (7)0.089 (2)
H2B0.19150.50000.06960.106*
H2A0.26950.50000.07380.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C50.042 (2)0.045 (2)0.056 (3)0.0000.002 (2)0.000
C40.051 (3)0.052 (3)0.056 (3)0.0000.008 (2)0.000
C30.043 (2)0.037 (2)0.075 (4)0.0000.014 (2)0.000
C20.039 (2)0.045 (2)0.067 (4)0.0000.001 (2)0.000
C10.045 (3)0.068 (3)0.058 (3)0.0000.004 (2)0.000
C60.056 (3)0.070 (4)0.093 (5)0.0000.031 (3)0.000
C70.040 (2)0.066 (3)0.072 (4)0.0000.005 (2)0.000
Cu0.0609 (4)0.0658 (4)0.0664 (5)0.0000.0122 (3)0.000
I10.0510 (2)0.0515 (2)0.0535 (2)0.0000.01474 (15)0.000
I20.0451 (2)0.0489 (2)0.0592 (2)0.0000.00176 (15)0.000
N10.041 (2)0.068 (3)0.055 (3)0.0000.0088 (19)0.000
N20.052 (3)0.147 (6)0.062 (4)0.0000.004 (2)0.000
Geometric parameters (Å, º) top
C5—N11.350 (7)Cu—I12.6482 (7)
C5—C41.376 (8)Cu—I1i2.6482 (7)
C5—C71.498 (7)Cu—I2ii2.6821 (8)
C4—C31.415 (7)Cu—I22.6821 (8)
C4—H40.9300Cu—Cui3.2437 (17)
C3—C21.368 (8)Cu—Cuii3.4751 (17)
C3—C61.502 (8)I1—Cui2.6482 (7)
C2—C11.365 (8)I1—I2iii9.643 (2)
C2—H20.9300I2—Cuii2.6821 (8)
C1—N21.340 (9)I2—I2ii4.0864 (15)
C1—N11.369 (7)I2—I1iv4.3778 (7)
C6—H6A0.9616N1—H10.8600
C6—H6B0.9578N2—H2B0.8600
C7—H7A0.9596N2—H2A0.8600
C7—H7B0.9621
N1—C5—C4118.7 (5)C5—C7—H7A109.7
N1—C5—C7117.9 (5)C5—C7—H7B109.7
C4—C5—C7123.4 (5)H7A—C7—H7B109.3
C5—C4—C3120.0 (5)I1—Cu—I1i104.47 (3)
C5—C4—H4120.0I1—Cu—I2ii116.387 (17)
C3—C4—H4120.0I1i—Cu—I2ii110.431 (19)
C2—C3—C4118.4 (5)I1—Cu—I2110.431 (19)
C2—C3—C6120.3 (5)I1i—Cu—I2116.387 (17)
C4—C3—C6121.2 (6)I2ii—Cu—I299.24 (3)
C1—C2—C3121.4 (5)Cu—I1—Cui75.53 (3)
C1—C2—H2119.3Cuii—I2—Cu80.76 (3)
C3—C2—H2119.3C5—N1—C1122.9 (5)
N2—C1—C2123.2 (5)C5—N1—H1118.6
N2—C1—N1118.2 (6)C1—N1—H1118.6
C2—C1—N1118.6 (6)C1—N2—H2B120.0
C3—C6—H6A109.2C1—N2—H2A120.0
C3—C6—H6B109.4H2B—N2—H2A120.0
H6A—C6—H6B109.5
N1—C5—C4—C30.0I2ii—Cu—I1—Cui122.04 (3)
C7—C5—C4—C3180.0I2—Cu—I1—Cui125.87 (2)
C5—C4—C3—C20.0I1—Cu—I2—Cuii122.76 (2)
C5—C4—C3—C6180.000 (1)I1i—Cu—I2—Cuii118.40 (2)
C4—C3—C2—C10.0C4—C5—N1—C10.0
C6—C3—C2—C1180.0C7—C5—N1—C1180.0
C3—C2—C1—N2180.0N2—C1—N1—C5180.0
C3—C2—C1—N10.0C2—C1—N1—C50.0
Symmetry codes: (i) x, y+1, z; (ii) x, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···I2iii0.862.963.753 (5)155
N2—H2B···I1i0.862.743.599 (5)174
N2—H2A···I2iii0.862.783.611 (6)162
Symmetry codes: (i) x, y+1, z; (iii) x+1/2, y+1/2, z.
 

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