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The title compound, (C12H16N2)2[PbI6], 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 PbI64− octa­hedra stabilize the structure. The slightly distorted PbI6 octa­hedra are isolated from each other, with the Pb atom located on a centre of inversion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001560/wm2087sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001560/wm2087Isup2.hkl
Contains datablock I

CCDC reference: 611025

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Computing details top

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 = 1345.17F(000) = 604.00
Triclinic, P1Dx = 2.694 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 8.467 (4) ÅCell parameters from 7936 reflections
b = 8.732 (5) Åθ = 3.2–27.5°
c = 12.921 (7) ŵ = 10.71 mm1
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-1Rint = 0.021
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.046, Tmax = 0.118k = 1111
8214 measured reflectionsl = 1616
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) = 0.050Δρmax = 0.63 e Å3
S = 1.01Δρmin = 1.42 e Å3
3772 reflectionsExtinction correction: Larson (1970), equation 22
161 parametersExtinction 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
xyzUiso*/Ueq
Pb10.50000.50000.50000.02882 (5)
I10.57743 (3)0.11652 (3)0.61376 (2)0.03396 (6)
I20.13654 (3)0.63929 (3)0.65670 (2)0.03586 (6)
I30.31380 (3)0.44383 (3)0.32498 (2)0.03629 (6)
N10.2722 (4)0.0441 (4)0.7523 (2)0.0327 (7)
N20.1290 (4)0.2431 (4)0.5576 (2)0.0391 (8)
C10.2635 (4)0.0455 (4)0.9268 (2)0.0304 (8)
C20.2384 (5)0.2145 (5)0.8840 (2)0.0377 (10)
C30.2167 (6)0.3326 (5)0.9481 (3)0.0478 (12)
C40.2227 (6)0.2885 (6)1.0582 (3)0.0507 (12)
C50.2514 (5)0.1267 (5)1.1003 (2)0.0449 (11)
C60.2709 (4)0.0017 (5)1.0380 (2)0.0350 (9)
C70.2991 (5)0.1679 (5)1.0811 (2)0.0421 (10)
C80.3114 (6)0.2862 (5)1.0211 (3)0.0496 (12)
C90.3043 (5)0.2465 (5)0.9106 (2)0.0421 (10)
C100.2816 (5)0.0842 (4)0.8674 (2)0.0334 (8)
C110.0839 (5)0.0683 (5)0.7248 (2)0.0359 (9)
C120.0724 (5)0.1069 (5)0.6071 (2)0.0367 (10)
H20.23690.24440.81160.045*
H30.19760.44390.91940.057*
H40.20690.37081.10160.061*
H50.25830.09811.17250.054*
H70.30950.19841.15290.050*
H80.32470.39471.05240.059*
H90.31460.32820.86850.050*
H1010.33640.00910.72690.039*
H1020.31480.14010.72400.039*
H1110.03690.17750.75550.043*
H1120.01090.00930.75490.043*
H1210.05090.14570.59520.044*
H1220.14930.00080.57360.044*
H2010.06470.33670.58840.047*
H2020.11450.26370.49170.047*
H2030.24020.20760.56420.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.02910 (11)0.02887 (11)0.03011 (10)0.01482 (8)0.00343 (6)0.00131 (6)
I10.03284 (12)0.03061 (12)0.03640 (12)0.01452 (11)0.00302 (9)0.00206 (9)
I20.03109 (12)0.04028 (14)0.03378 (12)0.01434 (11)0.00207 (9)0.00412 (10)
I30.03808 (13)0.03977 (14)0.03424 (12)0.01914 (12)0.00523 (10)0.00546 (10)
N10.0348 (16)0.0314 (16)0.0282 (13)0.0133 (13)0.0023 (11)0.0038 (11)
N20.0388 (18)0.0391 (18)0.0393 (15)0.0190 (16)0.0091 (13)0.0062 (13)
C10.0280 (17)0.0345 (19)0.0275 (14)0.0141 (15)0.0016 (13)0.0045 (13)
C20.045 (2)0.036 (2)0.0324 (16)0.0194 (18)0.0028 (15)0.0003 (15)
C30.059 (2)0.039 (2)0.049 (2)0.026 (2)0.004 (2)0.0050 (18)
C40.060 (2)0.055 (2)0.043 (2)0.028 (2)0.0035 (19)0.0173 (19)
C50.047 (2)0.057 (2)0.0305 (17)0.023 (2)0.0017 (16)0.0081 (17)
C60.0290 (18)0.042 (2)0.0281 (15)0.0127 (16)0.0022 (13)0.0002 (14)
C70.039 (2)0.048 (2)0.0300 (17)0.0156 (19)0.0003 (15)0.0058 (16)
C80.056 (2)0.038 (2)0.046 (2)0.020 (2)0.0002 (19)0.0082 (17)
C90.048 (2)0.035 (2)0.0414 (19)0.0190 (19)0.0001 (17)0.0041 (16)
C100.0340 (18)0.0344 (19)0.0259 (15)0.0131 (16)0.0002 (13)0.0022 (13)
C110.0345 (19)0.041 (2)0.0311 (16)0.0181 (17)0.0034 (14)0.0043 (14)
C120.036 (2)0.042 (2)0.0333 (17)0.0188 (18)0.0043 (15)0.0018 (15)
Geometric parameters (Å, º) top
Pb1—I13.2380 (19)C9—C101.372 (6)
Pb1—I1i3.2380 (19)C11—C121.513 (4)
Pb1—I23.1875 (18)N1—H1010.860
Pb1—I2i3.1875 (18)N1—H1020.860
Pb1—I33.1938 (18)N2—H2010.860
Pb1—I3i3.1938 (18)N2—H2020.860
N1—C101.478 (4)N2—H2030.860
N1—C111.506 (4)C2—H20.930
N2—C121.490 (6)C3—H30.930
C1—C21.418 (5)C4—H40.930
C1—C61.430 (4)C5—H50.930
C1—C101.407 (6)C7—H70.930
C2—C31.355 (6)C8—H80.930
C3—C41.414 (5)C9—H90.930
C4—C51.351 (7)C11—H1110.970
C5—C61.393 (7)C11—H1120.970
C6—C71.417 (6)C12—H1210.970
C7—C81.347 (7)C12—H1220.970
C8—C91.418 (5)
I1···N13.568 (3)H4···C8vii3.455
I2···N2ii3.595 (3)H4···H3x3.077
N1···I13.568 (3)H4···H8vii2.614
N2···I2ii3.595 (3)H5···I1iv3.213
C7···C11iii3.572 (5)H5···H101iv3.543
C11···C7iii3.572 (5)H5···H112iii2.808
I1···H23.378H7···I1iv3.592
I1···H5iv3.213H7···I3xiv3.512
I1···H7iv3.592H7···C11iii3.175
I1···H1012.727H7···H111iii2.892
I1···H121v3.237H7···H112iii2.616
I1···H122vi2.980H7···H121iii3.552
I1···H202vi3.445H8···I3xiv3.573
I1···H2032.752H8···C3xi3.442
I1···H203vi3.537H8···C4xi3.245
I2···H23.497H8···C8xii3.165
I2···H33.550H8···C9xii3.290
I2···H9vii3.461H8···H3xi2.995
I2···H102vii3.236H8···H4xi2.614
I2···H112vii3.296H8···H8xii2.889
I2···H121ii3.494H8···H9xii3.109
I2···H122vii3.207H8···H111iii3.547
I2···H2013.253H9···I2xi3.461
I2···H2022.857H9···I3vi3.499
I3···H4viii3.412H9···C3xi3.389
I3···H7ix3.512H9···H3xi2.557
I3···H83.573H9···H8xii3.109
I3···H9vi3.499H101···I12.727
I3···H102vi3.071H101···H5iv3.543
I3···H111ii3.420H102···I2xi3.236
I3···H121ii3.444H102···I3vi3.071
I3···H2012.987H111···I3ii3.420
I3···H2023.163H111···C7iii3.251
I3···H2033.549H111···H7iii2.892
N2···H201ii3.598H111···H8iii3.547
C3···H3x3.412H112···I2xi3.296
C3···H4x3.412H112···C5iii3.174
C3···H8vii3.442H112···C6iii3.273
C3···H9vii3.389H112···C7iii2.985
C4···H3x3.216H112···H5iii2.808
C4···H8vii3.245H112···H7iii2.616
C5···H112iii3.174H121···I1xv3.237
C6···H112iii3.273H121···I2ii3.494
C7···H111iii3.251H121···I3ii3.444
C7···H112iii2.985H121···H7iii3.552
C8···H3xi3.435H121···H121xvi3.541
C8···H4xi3.455H121···H122xvi3.107
C8···H8xii3.165H122···I1vi2.980
C9···H3xi3.204H122···I2xi3.207
C9···H8xii3.290H122···H121xvi3.107
C11···H7iii3.175H122···H122xvi3.432
H2···I13.378H201···I23.253
H2···I23.497H201···I3ii2.987
H3···I23.550H201···N2ii3.598
H3···C3x3.412H201···H201ii3.224
H3···C4x3.216H201···H202ii3.163
H3···C8vii3.435H202···I1vi3.445
H3···C9vii3.204H202···I2ii2.857
H3···H3x3.410H202···I33.163
H3···H4x3.077H202···H201ii3.163
H3···H8vii2.995H203···I12.752
H3···H9vii2.557H203···I1vi3.537
H4···I3xiii3.412H203···I33.549
H4···C3x3.412
I1—Pb1—I1i180.0C10—N1—H102108.6
I1—Pb1—I286.444 (5)C11—N1—H101108.6
I1—Pb1—I2i93.556 (5)C11—N1—H102108.6
I1—Pb1—I389.799 (6)H101—N1—H102109.5
I1—Pb1—I3i90.201 (6)C12—N2—H201109.5
I1i—Pb1—I293.556 (5)C12—N2—H202109.5
I1i—Pb1—I2i86.444 (5)C12—N2—H203109.5
I1i—Pb1—I390.201 (6)H201—N2—H202109.5
I1i—Pb1—I3i89.799 (6)H201—N2—H203109.5
I2—Pb1—I2i180.0H202—N2—H203109.5
I2—Pb1—I392.575 (6)C1—C2—H2119.8
I2—Pb1—I3i87.425 (6)C3—C2—H2119.8
I2i—Pb1—I387.425 (6)C2—C3—H3119.6
I2i—Pb1—I3i92.575 (6)C4—C3—H3119.6
I3—Pb1—I3i180.0C3—C4—H4120.1
C10—N1—C11113.1 (2)C5—C4—H4120.1
C2—C1—C6118.5 (3)C4—C5—H5119.2
C2—C1—C10124.6 (3)C6—C5—H5119.2
C6—C1—C10116.9 (3)C6—C7—H7119.0
C1—C2—C3120.3 (3)C8—C7—H7119.0
C2—C3—C4120.8 (4)C7—C8—H8119.7
C3—C4—C5119.9 (4)C9—C8—H8119.7
C4—C5—C6121.5 (3)C8—C9—H9120.9
C1—C6—C5119.0 (3)C10—C9—H9120.9
C1—C6—C7118.8 (3)N1—C11—H111108.5
C5—C6—C7122.2 (3)N1—C11—H112108.5
C6—C7—C8121.9 (3)C12—C11—H111108.5
C7—C8—C9120.5 (4)C12—C11—H112108.5
C8—C9—C10118.1 (4)H111—C11—H112109.5
N1—C10—C1118.9 (3)N2—C12—H121108.5
N1—C10—C9117.5 (3)N2—C12—H122108.5
C1—C10—C9123.6 (3)C11—C12—H121108.5
N1—C11—C12113.4 (2)C11—C12—H122108.5
N2—C12—C11113.4 (4)H121—C12—H122109.5
C10—N1—H101108.6
C10—N1—C11—C12178.8 (4)C1—C2—C3—C41.5 (7)
C11—N1—C10—C175.6 (5)C2—C3—C4—C50.4 (6)
C11—N1—C10—C9103.1 (4)C3—C4—C5—C61.7 (7)
C2—C1—C6—C50.7 (5)C4—C5—C6—C11.1 (6)
C2—C1—C6—C7178.9 (3)C4—C5—C6—C7179.3 (4)
C6—C1—C2—C32.0 (6)C1—C6—C7—C82.9 (6)
C2—C1—C10—N10.8 (5)C5—C6—C7—C8177.6 (4)
C2—C1—C10—C9179.4 (4)C6—C7—C8—C92.8 (6)
C10—C1—C2—C3177.9 (4)C7—C8—C9—C101.0 (6)
C6—C1—C10—N1179.1 (3)C8—C9—C10—N1179.3 (3)
C6—C1—C10—C90.5 (5)C8—C9—C10—C10.6 (6)
C10—C1—C6—C5179.2 (3)N1—C11—C12—N277.6 (4)
C10—C1—C6—C71.2 (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, z1; (ix) x, y+1, z1; (x) x, y+1, z+2; (xi) x, y1, z; (xii) x+1, y1, z+2; (xiii) x, y, z+1; (xiv) x, y1, z+1; (xv) x1, y, z; (xvi) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···I10.862.733.568 (4)166
N1—H102···I3vi0.863.073.744 (5)137
N2—H201···I3ii0.862.993.695 (5)141
N2—H202···I30.863.163.698 (6)123
N2—H202···I2ii0.862.863.595 (5)145
N2—H203···I10.862.753.604 (4)171
Symmetry codes: (ii) x, y+1, z+1; (vi) x+1, y, z+1.
 

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