Bis[N-(1-naphth­yl)ethyl­enediammonium] hexa­iodo­plumbate(II)

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.

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

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)

Crystal data

(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) Å^3

Data collection

Rigaku R-AXIS RAPID CCD area-detector diffractometer	3449 reflections with F^2 > 2σ(F^2)
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

Refinement on F^2	w = 1/[0.0001Fo^2 + 1.12σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.020	(Δ/σ)max < 0.001
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Pb1—I1	3.2380 (19)	C9—C10	1.372 (6)
Pb1—I1^i	3.2380 (19)	C11—C12	1.513 (4)
Pb1—I2	3.1875 (18)	N1—H101	0.860
Pb1—I2^i	3.1875 (18)	N1—H102	0.860
Pb1—I3	3.1938 (18)	N2—H201	0.860
Pb1—I3^i	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···C8^vii	3.455
I2···N2^ii	3.595 (3)	H4···H3^x	3.077
N1···I1	3.568 (3)	H4···H8^vii	2.614
N2···I2^ii	3.595 (3)	H5···I1^iv	3.213
C7···C11^iii	3.572 (5)	H5···H101^iv	3.543
C11···C7^iii	3.572 (5)	H5···H112^iii	2.808
I1···H2	3.378	H7···I1^iv	3.592
I1···H5^iv	3.213	H7···I3^xiv	3.512
I1···H7^iv	3.592	H7···C11^iii	3.175
I1···H101	2.727	H7···H111^iii	2.892
I1···H121^v	3.237	H7···H112^iii	2.616
I1···H122^vi	2.980	H7···H121^iii	3.552
I1···H202^vi	3.445	H8···I3^xiv	3.573
I1···H203	2.752	H8···C3^xi	3.442
I1···H203^vi	3.537	H8···C4^xi	3.245
I2···H2	3.497	H8···C8^xii	3.165
I2···H3	3.550	H8···C9^xii	3.290
I2···H9^vii	3.461	H8···H3^xi	2.995
I2···H102^vii	3.236	H8···H4^xi	2.614
I2···H112^vii	3.296	H8···H8^xii	2.889
I2···H121^ii	3.494	H8···H9^xii	3.109
I2···H122^vii	3.207	H8···H111^iii	3.547
I2···H201	3.253	H9···I2^xi	3.461
I2···H202	2.857	H9···I3^vi	3.499
I3···H4^viii	3.412	H9···C3^xi	3.389
I3···H7^ix	3.512	H9···H3^xi	2.557
I3···H8	3.573	H9···H8^xii	3.109
I3···H9^vi	3.499	H101···I1	2.727
I3···H102^vi	3.071	H101···H5^iv	3.543
I3···H111^ii	3.420	H102···I2^xi	3.236
I3···H121^ii	3.444	H102···I3^vi	3.071
I3···H201	2.987	H111···I3^ii	3.420
I3···H202	3.163	H111···C7^iii	3.251
I3···H203	3.549	H111···H7^iii	2.892
N2···H201^ii	3.598	H111···H8^iii	3.547
C3···H3^x	3.412	H112···I2^xi	3.296
C3···H4^x	3.412	H112···C5^iii	3.174
C3···H8^vii	3.442	H112···C6^iii	3.273
C3···H9^vii	3.389	H112···C7^iii	2.985
C4···H3^x	3.216	H112···H5^iii	2.808
C4···H8^vii	3.245	H112···H7^iii	2.616
C5···H112^iii	3.174	H121···I1^xv	3.237
C6···H112^iii	3.273	H121···I2^ii	3.494
C7···H111^iii	3.251	H121···I3^ii	3.444
C7···H112^iii	2.985	H121···H7^iii	3.552
C8···H3^xi	3.435	H121···H121^xvi	3.541
C8···H4^xi	3.455	H121···H122^xvi	3.107
C8···H8^xii	3.165	H122···I1^vi	2.980
C9···H3^xi	3.204	H122···I2^xi	3.207
C9···H8^xii	3.290	H122···H121^xvi	3.107
C11···H7^iii	3.175	H122···H122^xvi	3.432
H2···I1	3.378	H201···I2	3.253
H2···I2	3.497	H201···I3^ii	2.987
H3···I2	3.550	H201···N2^ii	3.598
H3···C3^x	3.412	H201···H201^ii	3.224
H3···C4^x	3.216	H201···H202^ii	3.163
H3···C8^vii	3.435	H202···I1^vi	3.445
H3···C9^vii	3.204	H202···I2^ii	2.857
H3···H3^x	3.410	H202···I3	3.163
H3···H4^x	3.077	H202···H201^ii	3.163
H3···H8^vii	2.995	H203···I1	2.752
H3···H9^vii	2.557	H203···I1^vi	3.537
H4···I3^xiii	3.412	H203···I3	3.549
H4···C3^x	3.412
I1—Pb1—I1^i	180.0	C10—N1—H102	108.6
I1—Pb1—I2	86.444 (5)	C11—N1—H101	108.6
I1—Pb1—I2^i	93.556 (5)	C11—N1—H102	108.6
I1—Pb1—I3	89.799 (6)	H101—N1—H102	109.5
I1—Pb1—I3^i	90.201 (6)	C12—N2—H201	109.5
I1^i—Pb1—I2	93.556 (5)	C12—N2—H202	109.5
I1^i—Pb1—I2^i	86.444 (5)	C12—N2—H203	109.5
I1^i—Pb1—I3	90.201 (6)	H201—N2—H202	109.5
I1^i—Pb1—I3^i	89.799 (6)	H201—N2—H203	109.5
I2—Pb1—I2^i	180.0	H202—N2—H203	109.5
I2—Pb1—I3	92.575 (6)	C1—C2—H2	119.8
I2—Pb1—I3^i	87.425 (6)	C3—C2—H2	119.8
I2^i—Pb1—I3	87.425 (6)	C2—C3—H3	119.6
I2^i—Pb1—I3^i	92.575 (6)	C4—C3—H3	119.6
I3—Pb1—I3^i	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)

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···I3^vi	0.86	3.07	3.744 (5)	137
N2—H201···I3^ii	0.86	2.99	3.695 (5)	141
N2—H202···I3	0.86	3.16	3.698 (6)	123
N2—H202···I2^ii	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.