In the title compound, (2-amino-4,6-dimethylpyridinium) diiodocuprate(I), (C
7H
11N
2)[CuI
2], 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
CCDC reference: 231825
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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 = 440.52 | Dx = 2.509 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2y | Cell parameters from 4476 reflections |
a = 19.003 (4) Å | θ = 2.2–30.0° |
b = 6.7188 (13) Å | µ = 7.16 mm−1 |
c = 9.2156 (18) Å | T = 296 K |
β = 99.37 (3)° | Plate, colourless |
V = 1160.9 (4) Å3 | 0.44 × 0.31 × 0.05 mm |
Z = 4 | |
Data collection top
Bruker/Siemens SMART APEX CCD diffractometer | 1434 independent reflections |
Radiation source: fine-focus sealed tube | 1316 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.3 pixels mm-1 | θmax = 27.5°, θmin = 2.2° |
ω scans | h = −24→24 |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | k = −8→8 |
Tmin = 0.070, Tmax = 0.697 | l = −11→11 |
7083 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-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 parameters | Δρmax = 1.08 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C5 | 0.3372 (3) | 0.5000 | 0.3384 (6) | 0.0482 (11) | |
C4 | 0.2845 (3) | 0.5000 | 0.4248 (7) | 0.0530 (12) | |
H4 | 0.2967 | 0.5000 | 0.5267 | 0.064* | |
C3 | 0.2119 (3) | 0.5000 | 0.3586 (7) | 0.0512 (12) | |
C2 | 0.1959 (3) | 0.5000 | 0.2084 (7) | 0.0513 (12) | |
H2 | 0.1484 | 0.5000 | 0.1636 | 0.062* | |
C1 | 0.2483 (3) | 0.5000 | 0.1230 (7) | 0.0585 (13) | |
C6 | 0.1533 (3) | 0.5000 | 0.4500 (9) | 0.0710 (17) | |
H6A | 0.1079 | 0.5000 | 0.3861 | 0.106* | |
H6B | 0.1572 | 0.3833 | 0.5105 | 0.106* | |
C7 | 0.4152 (3) | 0.5000 | 0.3995 (7) | 0.0596 (14) | |
H7A | 0.4424 | 0.5000 | 0.3204 | 0.089* | |
H7B | 0.4269 | 0.6167 | 0.4591 | 0.089* | |
Cu | 0.0000 | 0.25861 (11) | 0.0000 | 0.0642 (2) | |
I1 | −0.049357 (18) | 0.5000 | 0.18719 (4) | 0.05131 (13) | |
I2 | 0.093627 (17) | 0.0000 | 0.14488 (4) | 0.05218 (13) | |
N1 | 0.3179 (2) | 0.5000 | 0.1907 (5) | 0.0548 (11) | |
H1 | 0.3509 | 0.5000 | 0.1369 | 0.066* | |
N2 | 0.2348 (3) | 0.5000 | −0.0244 (7) | 0.089 (2) | |
H2B | 0.1915 | 0.5000 | −0.0696 | 0.106* | |
H2A | 0.2695 | 0.5000 | −0.0738 | 0.106* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C5 | 0.042 (2) | 0.045 (2) | 0.056 (3) | 0.000 | 0.002 (2) | 0.000 |
C4 | 0.051 (3) | 0.052 (3) | 0.056 (3) | 0.000 | 0.008 (2) | 0.000 |
C3 | 0.043 (2) | 0.037 (2) | 0.075 (4) | 0.000 | 0.014 (2) | 0.000 |
C2 | 0.039 (2) | 0.045 (2) | 0.067 (4) | 0.000 | −0.001 (2) | 0.000 |
C1 | 0.045 (3) | 0.068 (3) | 0.058 (3) | 0.000 | −0.004 (2) | 0.000 |
C6 | 0.056 (3) | 0.070 (4) | 0.093 (5) | 0.000 | 0.031 (3) | 0.000 |
C7 | 0.040 (2) | 0.066 (3) | 0.072 (4) | 0.000 | 0.005 (2) | 0.000 |
Cu | 0.0609 (4) | 0.0658 (4) | 0.0664 (5) | 0.000 | 0.0122 (3) | 0.000 |
I1 | 0.0510 (2) | 0.0515 (2) | 0.0535 (2) | 0.000 | 0.01474 (15) | 0.000 |
I2 | 0.0451 (2) | 0.0489 (2) | 0.0592 (2) | 0.000 | −0.00176 (15) | 0.000 |
N1 | 0.041 (2) | 0.068 (3) | 0.055 (3) | 0.000 | 0.0088 (19) | 0.000 |
N2 | 0.052 (3) | 0.147 (6) | 0.062 (4) | 0.000 | −0.004 (2) | 0.000 |
Geometric parameters (Å, º) top
C5—N1 | 1.350 (7) | Cu—I1 | 2.6482 (7) |
C5—C4 | 1.376 (8) | Cu—I1i | 2.6482 (7) |
C5—C7 | 1.498 (7) | Cu—I2ii | 2.6821 (8) |
C4—C3 | 1.415 (7) | Cu—I2 | 2.6821 (8) |
C4—H4 | 0.9300 | Cu—Cui | 3.2437 (17) |
C3—C2 | 1.368 (8) | Cu—Cuii | 3.4751 (17) |
C3—C6 | 1.502 (8) | I1—Cui | 2.6482 (7) |
C2—C1 | 1.365 (8) | I1—I2iii | 9.643 (2) |
C2—H2 | 0.9300 | I2—Cuii | 2.6821 (8) |
C1—N2 | 1.340 (9) | I2—I2ii | 4.0864 (15) |
C1—N1 | 1.369 (7) | I2—I1iv | 4.3778 (7) |
C6—H6A | 0.9616 | N1—H1 | 0.8600 |
C6—H6B | 0.9578 | N2—H2B | 0.8600 |
C7—H7A | 0.9596 | N2—H2A | 0.8600 |
C7—H7B | 0.9621 | | |
| | | |
N1—C5—C4 | 118.7 (5) | C5—C7—H7A | 109.7 |
N1—C5—C7 | 117.9 (5) | C5—C7—H7B | 109.7 |
C4—C5—C7 | 123.4 (5) | H7A—C7—H7B | 109.3 |
C5—C4—C3 | 120.0 (5) | I1—Cu—I1i | 104.47 (3) |
C5—C4—H4 | 120.0 | I1—Cu—I2ii | 116.387 (17) |
C3—C4—H4 | 120.0 | I1i—Cu—I2ii | 110.431 (19) |
C2—C3—C4 | 118.4 (5) | I1—Cu—I2 | 110.431 (19) |
C2—C3—C6 | 120.3 (5) | I1i—Cu—I2 | 116.387 (17) |
C4—C3—C6 | 121.2 (6) | I2ii—Cu—I2 | 99.24 (3) |
C1—C2—C3 | 121.4 (5) | Cu—I1—Cui | 75.53 (3) |
C1—C2—H2 | 119.3 | Cuii—I2—Cu | 80.76 (3) |
C3—C2—H2 | 119.3 | C5—N1—C1 | 122.9 (5) |
N2—C1—C2 | 123.2 (5) | C5—N1—H1 | 118.6 |
N2—C1—N1 | 118.2 (6) | C1—N1—H1 | 118.6 |
C2—C1—N1 | 118.6 (6) | C1—N2—H2B | 120.0 |
C3—C6—H6A | 109.2 | C1—N2—H2A | 120.0 |
C3—C6—H6B | 109.4 | H2B—N2—H2A | 120.0 |
H6A—C6—H6B | 109.5 | | |
| | | |
N1—C5—C4—C3 | 0.0 | I2ii—Cu—I1—Cui | −122.04 (3) |
C7—C5—C4—C3 | 180.0 | I2—Cu—I1—Cui | 125.87 (2) |
C5—C4—C3—C2 | 0.0 | I1—Cu—I2—Cuii | 122.76 (2) |
C5—C4—C3—C6 | 180.000 (1) | I1i—Cu—I2—Cuii | −118.40 (2) |
C4—C3—C2—C1 | 0.0 | C4—C5—N1—C1 | 0.0 |
C6—C3—C2—C1 | 180.0 | C7—C5—N1—C1 | 180.0 |
C3—C2—C1—N2 | 180.0 | N2—C1—N1—C5 | 180.0 |
C3—C2—C1—N1 | 0.0 | C2—C1—N1—C5 | 0.0 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z; (iii) −x+1/2, −y+1/2, −z; (iv) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I2iii | 0.86 | 2.96 | 3.753 (5) | 155 |
N2—H2B···I1i | 0.86 | 2.74 | 3.599 (5) | 174 |
N2—H2A···I2iii | 0.86 | 2.78 | 3.611 (6) | 162 |
Symmetry codes: (i) −x, −y+1, −z; (iii) −x+1/2, −y+1/2, −z. |