The title compound, (C
12H
16N
2)
2[PbI
6], is an organic–inorganic salt, with two doubly protonated
N-(1-naphthyl)ethylenediamine groups as the cations and one octahedral hexaiodoplumbate(II) as the anion. The stucture consists of alternating inorganic and organic layers parallel to the
bc plane. Simple face-to-face aromatic stacking interactions occur between parallel naphthalene systems in the organic layers, and N—H
I hydrogen bonds between the ethylenediammonium groups and PbI
64− octahedra stabilize the structure. The slightly distorted PbI
6 octahedra are isolated from each other, with the Pb atom located on a centre of inversion.
Supporting information
CCDC reference: 611025
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.020
- wR factor = 0.050
- Data-to-parameter ratio = 23.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pb1 - I3 .. 8.94 su
PLAT420_ALERT_2_C D-H Without Acceptor N1 - H102 ... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H102 .. I3 .. 3.07 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H202 .. I3 .. 3.16 Ang.
PLAT732_ALERT_1_C Angle Calc 86.45(2), Rep 86.44 ...... 4.00 su-Ra
I1 -PB1 -I2 1.555 1.555 1.555
PLAT732_ALERT_1_C Angle Calc 89.80(2), Rep 89.80(1) ...... 3.33 su-Ra
I1 -PB1 -I3 1.555 1.555 1.555
PLAT732_ALERT_1_C Angle Calc 92.58(2), Rep 92.57(1) ...... 3.33 su-Ra
I2 -PB1 -I3 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 235
in a concentrated [Aqueous?] HI solution (10 ml, 45wt%~; Shanghai Chemical
If you require a ~ then it should be escaped
with a \, i.e. \~
Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: PROCESS-AUTO (Rigaku,1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
Bis[
N-(1-naphthyl)ethylenediammonium] hexaiodoplumbate(II)
top
Crystal data top
(C12H16N2)2[PbI6] | Z = 1 |
Mr = 1345.17 | F(000) = 604.00 |
Triclinic, P1 | Dx = 2.694 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71075 Å |
a = 8.467 (4) Å | Cell parameters from 7936 reflections |
b = 8.732 (5) Å | θ = 3.2–27.5° |
c = 12.921 (7) Å | µ = 10.71 mm−1 |
α = 80.49 (2)° | T = 298 K |
β = 79.691 (18)° | Chunk, yellow |
γ = 62.36 (2)° | 0.33 × 0.27 × 0.20 mm |
V = 829.0 (7) Å3 | |
Data collection top
Rigaku R-AXIS RAPID CCD area-detector diffractometer | 3449 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.021 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.046, Tmax = 0.118 | k = −11→11 |
8214 measured reflections | l = −16→16 |
3772 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[0.0001Fo2 + 1.12σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.020 | (Δ/σ)max < 0.001 |
wR(F2) = 0.050 | Δρmax = 0.63 e Å−3 |
S = 1.01 | Δρmin = −1.42 e Å−3 |
3772 reflections | Extinction correction: Larson (1970), equation 22 |
161 parameters | Extinction coefficient: 18.6 (11) |
H-atom parameters constrained | |
Special details top
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Pb1 | 0.5000 | 0.5000 | 0.5000 | 0.02882 (5) | |
I1 | 0.57743 (3) | 0.11652 (3) | 0.61376 (2) | 0.03396 (6) | |
I2 | 0.13654 (3) | 0.63929 (3) | 0.65670 (2) | 0.03586 (6) | |
I3 | 0.31380 (3) | 0.44383 (3) | 0.32498 (2) | 0.03629 (6) | |
N1 | 0.2722 (4) | −0.0441 (4) | 0.7523 (2) | 0.0327 (7) | |
N2 | 0.1290 (4) | 0.2431 (4) | 0.5576 (2) | 0.0391 (8) | |
C1 | 0.2635 (4) | 0.0455 (4) | 0.9268 (2) | 0.0304 (8) | |
C2 | 0.2384 (5) | 0.2145 (5) | 0.8840 (2) | 0.0377 (10) | |
C3 | 0.2167 (6) | 0.3326 (5) | 0.9481 (3) | 0.0478 (12) | |
C4 | 0.2227 (6) | 0.2885 (6) | 1.0582 (3) | 0.0507 (12) | |
C5 | 0.2514 (5) | 0.1267 (5) | 1.1003 (2) | 0.0449 (11) | |
C6 | 0.2709 (4) | 0.0017 (5) | 1.0380 (2) | 0.0350 (9) | |
C7 | 0.2991 (5) | −0.1679 (5) | 1.0811 (2) | 0.0421 (10) | |
C8 | 0.3114 (6) | −0.2862 (5) | 1.0211 (3) | 0.0496 (12) | |
C9 | 0.3043 (5) | −0.2465 (5) | 0.9106 (2) | 0.0421 (10) | |
C10 | 0.2816 (5) | −0.0842 (4) | 0.8674 (2) | 0.0334 (8) | |
C11 | 0.0839 (5) | 0.0683 (5) | 0.7248 (2) | 0.0359 (9) | |
C12 | 0.0724 (5) | 0.1069 (5) | 0.6071 (2) | 0.0367 (10) | |
H2 | 0.2369 | 0.2444 | 0.8116 | 0.045* | |
H3 | 0.1976 | 0.4439 | 0.9194 | 0.057* | |
H4 | 0.2069 | 0.3708 | 1.1016 | 0.061* | |
H5 | 0.2583 | 0.0981 | 1.1725 | 0.054* | |
H7 | 0.3095 | −0.1984 | 1.1529 | 0.050* | |
H8 | 0.3247 | −0.3947 | 1.0524 | 0.059* | |
H9 | 0.3146 | −0.3282 | 0.8685 | 0.050* | |
H101 | 0.3364 | 0.0091 | 0.7269 | 0.039* | |
H102 | 0.3148 | −0.1401 | 0.7240 | 0.039* | |
H111 | 0.0369 | 0.1775 | 0.7555 | 0.043* | |
H112 | 0.0109 | 0.0093 | 0.7549 | 0.043* | |
H121 | −0.0509 | 0.1457 | 0.5952 | 0.044* | |
H122 | 0.1493 | 0.0008 | 0.5736 | 0.044* | |
H201 | 0.0647 | 0.3367 | 0.5884 | 0.047* | |
H202 | 0.1145 | 0.2637 | 0.4917 | 0.047* | |
H203 | 0.2402 | 0.2076 | 0.5642 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pb1 | 0.02910 (11) | 0.02887 (11) | 0.03011 (10) | −0.01482 (8) | −0.00343 (6) | −0.00131 (6) |
I1 | 0.03284 (12) | 0.03061 (12) | 0.03640 (12) | −0.01452 (11) | −0.00302 (9) | 0.00206 (9) |
I2 | 0.03109 (12) | 0.04028 (14) | 0.03378 (12) | −0.01434 (11) | −0.00207 (9) | −0.00412 (10) |
I3 | 0.03808 (13) | 0.03977 (14) | 0.03424 (12) | −0.01914 (12) | −0.00523 (10) | −0.00546 (10) |
N1 | 0.0348 (16) | 0.0314 (16) | 0.0282 (13) | −0.0133 (13) | 0.0023 (11) | −0.0038 (11) |
N2 | 0.0388 (18) | 0.0391 (18) | 0.0393 (15) | −0.0190 (16) | −0.0091 (13) | 0.0062 (13) |
C1 | 0.0280 (17) | 0.0345 (19) | 0.0275 (14) | −0.0141 (15) | 0.0016 (13) | −0.0045 (13) |
C2 | 0.045 (2) | 0.036 (2) | 0.0324 (16) | −0.0194 (18) | −0.0028 (15) | 0.0003 (15) |
C3 | 0.059 (2) | 0.039 (2) | 0.049 (2) | −0.026 (2) | −0.004 (2) | −0.0050 (18) |
C4 | 0.060 (2) | 0.055 (2) | 0.043 (2) | −0.028 (2) | −0.0035 (19) | −0.0173 (19) |
C5 | 0.047 (2) | 0.057 (2) | 0.0305 (17) | −0.023 (2) | −0.0017 (16) | −0.0081 (17) |
C6 | 0.0290 (18) | 0.042 (2) | 0.0281 (15) | −0.0127 (16) | −0.0022 (13) | 0.0002 (14) |
C7 | 0.039 (2) | 0.048 (2) | 0.0300 (17) | −0.0156 (19) | −0.0003 (15) | 0.0058 (16) |
C8 | 0.056 (2) | 0.038 (2) | 0.046 (2) | −0.020 (2) | 0.0002 (19) | 0.0082 (17) |
C9 | 0.048 (2) | 0.035 (2) | 0.0414 (19) | −0.0190 (19) | 0.0001 (17) | −0.0041 (16) |
C10 | 0.0340 (18) | 0.0344 (19) | 0.0259 (15) | −0.0131 (16) | −0.0002 (13) | 0.0022 (13) |
C11 | 0.0345 (19) | 0.041 (2) | 0.0311 (16) | −0.0181 (17) | 0.0034 (14) | −0.0043 (14) |
C12 | 0.036 (2) | 0.042 (2) | 0.0333 (17) | −0.0188 (18) | −0.0043 (15) | −0.0018 (15) |
Geometric parameters (Å, º) top
Pb1—I1 | 3.2380 (19) | C9—C10 | 1.372 (6) |
Pb1—I1i | 3.2380 (19) | C11—C12 | 1.513 (4) |
Pb1—I2 | 3.1875 (18) | N1—H101 | 0.860 |
Pb1—I2i | 3.1875 (18) | N1—H102 | 0.860 |
Pb1—I3 | 3.1938 (18) | N2—H201 | 0.860 |
Pb1—I3i | 3.1938 (18) | N2—H202 | 0.860 |
N1—C10 | 1.478 (4) | N2—H203 | 0.860 |
N1—C11 | 1.506 (4) | C2—H2 | 0.930 |
N2—C12 | 1.490 (6) | C3—H3 | 0.930 |
C1—C2 | 1.418 (5) | C4—H4 | 0.930 |
C1—C6 | 1.430 (4) | C5—H5 | 0.930 |
C1—C10 | 1.407 (6) | C7—H7 | 0.930 |
C2—C3 | 1.355 (6) | C8—H8 | 0.930 |
C3—C4 | 1.414 (5) | C9—H9 | 0.930 |
C4—C5 | 1.351 (7) | C11—H111 | 0.970 |
C5—C6 | 1.393 (7) | C11—H112 | 0.970 |
C6—C7 | 1.417 (6) | C12—H121 | 0.970 |
C7—C8 | 1.347 (7) | C12—H122 | 0.970 |
C8—C9 | 1.418 (5) | | |
| | | |
I1···N1 | 3.568 (3) | H4···C8vii | 3.455 |
I2···N2ii | 3.595 (3) | H4···H3x | 3.077 |
N1···I1 | 3.568 (3) | H4···H8vii | 2.614 |
N2···I2ii | 3.595 (3) | H5···I1iv | 3.213 |
C7···C11iii | 3.572 (5) | H5···H101iv | 3.543 |
C11···C7iii | 3.572 (5) | H5···H112iii | 2.808 |
I1···H2 | 3.378 | H7···I1iv | 3.592 |
I1···H5iv | 3.213 | H7···I3xiv | 3.512 |
I1···H7iv | 3.592 | H7···C11iii | 3.175 |
I1···H101 | 2.727 | H7···H111iii | 2.892 |
I1···H121v | 3.237 | H7···H112iii | 2.616 |
I1···H122vi | 2.980 | H7···H121iii | 3.552 |
I1···H202vi | 3.445 | H8···I3xiv | 3.573 |
I1···H203 | 2.752 | H8···C3xi | 3.442 |
I1···H203vi | 3.537 | H8···C4xi | 3.245 |
I2···H2 | 3.497 | H8···C8xii | 3.165 |
I2···H3 | 3.550 | H8···C9xii | 3.290 |
I2···H9vii | 3.461 | H8···H3xi | 2.995 |
I2···H102vii | 3.236 | H8···H4xi | 2.614 |
I2···H112vii | 3.296 | H8···H8xii | 2.889 |
I2···H121ii | 3.494 | H8···H9xii | 3.109 |
I2···H122vii | 3.207 | H8···H111iii | 3.547 |
I2···H201 | 3.253 | H9···I2xi | 3.461 |
I2···H202 | 2.857 | H9···I3vi | 3.499 |
I3···H4viii | 3.412 | H9···C3xi | 3.389 |
I3···H7ix | 3.512 | H9···H3xi | 2.557 |
I3···H8 | 3.573 | H9···H8xii | 3.109 |
I3···H9vi | 3.499 | H101···I1 | 2.727 |
I3···H102vi | 3.071 | H101···H5iv | 3.543 |
I3···H111ii | 3.420 | H102···I2xi | 3.236 |
I3···H121ii | 3.444 | H102···I3vi | 3.071 |
I3···H201 | 2.987 | H111···I3ii | 3.420 |
I3···H202 | 3.163 | H111···C7iii | 3.251 |
I3···H203 | 3.549 | H111···H7iii | 2.892 |
N2···H201ii | 3.598 | H111···H8iii | 3.547 |
C3···H3x | 3.412 | H112···I2xi | 3.296 |
C3···H4x | 3.412 | H112···C5iii | 3.174 |
C3···H8vii | 3.442 | H112···C6iii | 3.273 |
C3···H9vii | 3.389 | H112···C7iii | 2.985 |
C4···H3x | 3.216 | H112···H5iii | 2.808 |
C4···H8vii | 3.245 | H112···H7iii | 2.616 |
C5···H112iii | 3.174 | H121···I1xv | 3.237 |
C6···H112iii | 3.273 | H121···I2ii | 3.494 |
C7···H111iii | 3.251 | H121···I3ii | 3.444 |
C7···H112iii | 2.985 | H121···H7iii | 3.552 |
C8···H3xi | 3.435 | H121···H121xvi | 3.541 |
C8···H4xi | 3.455 | H121···H122xvi | 3.107 |
C8···H8xii | 3.165 | H122···I1vi | 2.980 |
C9···H3xi | 3.204 | H122···I2xi | 3.207 |
C9···H8xii | 3.290 | H122···H121xvi | 3.107 |
C11···H7iii | 3.175 | H122···H122xvi | 3.432 |
H2···I1 | 3.378 | H201···I2 | 3.253 |
H2···I2 | 3.497 | H201···I3ii | 2.987 |
H3···I2 | 3.550 | H201···N2ii | 3.598 |
H3···C3x | 3.412 | H201···H201ii | 3.224 |
H3···C4x | 3.216 | H201···H202ii | 3.163 |
H3···C8vii | 3.435 | H202···I1vi | 3.445 |
H3···C9vii | 3.204 | H202···I2ii | 2.857 |
H3···H3x | 3.410 | H202···I3 | 3.163 |
H3···H4x | 3.077 | H202···H201ii | 3.163 |
H3···H8vii | 2.995 | H203···I1 | 2.752 |
H3···H9vii | 2.557 | H203···I1vi | 3.537 |
H4···I3xiii | 3.412 | H203···I3 | 3.549 |
H4···C3x | 3.412 | | |
| | | |
I1—Pb1—I1i | 180.0 | C10—N1—H102 | 108.6 |
I1—Pb1—I2 | 86.444 (5) | C11—N1—H101 | 108.6 |
I1—Pb1—I2i | 93.556 (5) | C11—N1—H102 | 108.6 |
I1—Pb1—I3 | 89.799 (6) | H101—N1—H102 | 109.5 |
I1—Pb1—I3i | 90.201 (6) | C12—N2—H201 | 109.5 |
I1i—Pb1—I2 | 93.556 (5) | C12—N2—H202 | 109.5 |
I1i—Pb1—I2i | 86.444 (5) | C12—N2—H203 | 109.5 |
I1i—Pb1—I3 | 90.201 (6) | H201—N2—H202 | 109.5 |
I1i—Pb1—I3i | 89.799 (6) | H201—N2—H203 | 109.5 |
I2—Pb1—I2i | 180.0 | H202—N2—H203 | 109.5 |
I2—Pb1—I3 | 92.575 (6) | C1—C2—H2 | 119.8 |
I2—Pb1—I3i | 87.425 (6) | C3—C2—H2 | 119.8 |
I2i—Pb1—I3 | 87.425 (6) | C2—C3—H3 | 119.6 |
I2i—Pb1—I3i | 92.575 (6) | C4—C3—H3 | 119.6 |
I3—Pb1—I3i | 180.0 | C3—C4—H4 | 120.1 |
C10—N1—C11 | 113.1 (2) | C5—C4—H4 | 120.1 |
C2—C1—C6 | 118.5 (3) | C4—C5—H5 | 119.2 |
C2—C1—C10 | 124.6 (3) | C6—C5—H5 | 119.2 |
C6—C1—C10 | 116.9 (3) | C6—C7—H7 | 119.0 |
C1—C2—C3 | 120.3 (3) | C8—C7—H7 | 119.0 |
C2—C3—C4 | 120.8 (4) | C7—C8—H8 | 119.7 |
C3—C4—C5 | 119.9 (4) | C9—C8—H8 | 119.7 |
C4—C5—C6 | 121.5 (3) | C8—C9—H9 | 120.9 |
C1—C6—C5 | 119.0 (3) | C10—C9—H9 | 120.9 |
C1—C6—C7 | 118.8 (3) | N1—C11—H111 | 108.5 |
C5—C6—C7 | 122.2 (3) | N1—C11—H112 | 108.5 |
C6—C7—C8 | 121.9 (3) | C12—C11—H111 | 108.5 |
C7—C8—C9 | 120.5 (4) | C12—C11—H112 | 108.5 |
C8—C9—C10 | 118.1 (4) | H111—C11—H112 | 109.5 |
N1—C10—C1 | 118.9 (3) | N2—C12—H121 | 108.5 |
N1—C10—C9 | 117.5 (3) | N2—C12—H122 | 108.5 |
C1—C10—C9 | 123.6 (3) | C11—C12—H121 | 108.5 |
N1—C11—C12 | 113.4 (2) | C11—C12—H122 | 108.5 |
N2—C12—C11 | 113.4 (4) | H121—C12—H122 | 109.5 |
C10—N1—H101 | 108.6 | | |
| | | |
C10—N1—C11—C12 | −178.8 (4) | C1—C2—C3—C4 | 1.5 (7) |
C11—N1—C10—C1 | −75.6 (5) | C2—C3—C4—C5 | 0.4 (6) |
C11—N1—C10—C9 | 103.1 (4) | C3—C4—C5—C6 | −1.7 (7) |
C2—C1—C6—C5 | 0.7 (5) | C4—C5—C6—C1 | 1.1 (6) |
C2—C1—C6—C7 | −178.9 (3) | C4—C5—C6—C7 | −179.3 (4) |
C6—C1—C2—C3 | −2.0 (6) | C1—C6—C7—C8 | −2.9 (6) |
C2—C1—C10—N1 | −0.8 (5) | C5—C6—C7—C8 | 177.6 (4) |
C2—C1—C10—C9 | −179.4 (4) | C6—C7—C8—C9 | 2.8 (6) |
C10—C1—C2—C3 | 177.9 (4) | C7—C8—C9—C10 | −1.0 (6) |
C6—C1—C10—N1 | 179.1 (3) | C8—C9—C10—N1 | −179.3 (3) |
C6—C1—C10—C9 | 0.5 (5) | C8—C9—C10—C1 | −0.6 (6) |
C10—C1—C6—C5 | −179.2 (3) | N1—C11—C12—N2 | −77.6 (4) |
C10—C1—C6—C7 | 1.2 (5) | | |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y, −z+2; (iv) −x+1, −y, −z+2; (v) x+1, y, z; (vi) −x+1, −y, −z+1; (vii) x, y+1, z; (viii) x, y, z−1; (ix) x, y+1, z−1; (x) −x, −y+1, −z+2; (xi) x, y−1, z; (xii) −x+1, −y−1, −z+2; (xiii) x, y, z+1; (xiv) x, y−1, z+1; (xv) x−1, y, z; (xvi) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H101···I1 | 0.86 | 2.73 | 3.568 (4) | 166 |
N1—H102···I3vi | 0.86 | 3.07 | 3.744 (5) | 137 |
N2—H201···I3ii | 0.86 | 2.99 | 3.695 (5) | 141 |
N2—H202···I3 | 0.86 | 3.16 | 3.698 (6) | 123 |
N2—H202···I2ii | 0.86 | 2.86 | 3.595 (5) | 145 |
N2—H203···I1 | 0.86 | 2.75 | 3.604 (4) | 171 |
Symmetry codes: (ii) −x, −y+1, −z+1; (vi) −x+1, −y, −z+1. |