A one-dimensional organic–inorganic hybrid compound [(CH₃)₂C=NHCH₂CH₂CH₃][PbI₃]

Crystals of the one-dimensional organic–inorganic lead iodide-based compound N-isopropyl­idenepropanaminium triiodo­plumbate(II), (C₆H₁₄N)[PbI₃], were prepared by slow evaporation at room temperature. In the inorganic sublattice, the PbI₆ octa­hedra form infinite one-dimensional chains sharing triangular faces. The inorganic PbI₃ chain and the organic cations are connected through N—H...I hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.027 Å
• R factor = 0.055
• wR factor = 0.152
• Data-to-parameter ratio = 31.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT342_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         28

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT420_ALERT_2_C D-H Without Acceptor       N      -   H1     ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  I2      ..       3.09 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  I3      ..       3.25 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   1 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

---

Computing details

Data collection: CAD-4 EXPRESS (Duisenberg, 1992; Macíček & Yordanov, 1992); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

N-isopropylidenepropanaminium triiodoplumbate

Crystal data

(C6H14N)[PbI3]	F(000) = 1192
Mr = 688.07	Dx = 3.094 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.533 (4) Å	θ = 11–20°
b = 16.291 (5) Å	µ = 17.65 mm^−1
c = 8.251 (3) Å	T = 293 K
β = 107.66 (3)°	Parallelipiped, yellow
V = 1477.2 (9) Å^3	0.24 × 0.16 × 0.12 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	2058 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.081
Graphite monochromator	θmax = 27.0°, θmin = 2.2°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = −20→0
Tmin = 0.045, Tmax = 0.126	l = −10→10
5585 measured reflections	2 standard reflections every 120 min
3207 independent reflections	intensity decay: 2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0773P)^2] where P = (Fo^2 + 2Fc^2)/3
3207 reflections	(Δ/σ)max < 0.001
103 parameters	Δρmax = 3.92 e Å^−3
0 restraints	Δρmin = −2.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Pb	0.19037 (5)	0.75154 (3)	0.56129 (6)	0.03966 (19)
I1	−0.00854 (9)	0.67843 (8)	0.71550 (12)	0.0521 (3)
I2	0.39061 (9)	0.66833 (8)	0.88216 (12)	0.0533 (3)
I3	0.19895 (9)	0.59649 (7)	0.34799 (11)	0.0492 (3)
C1	0.2476 (18)	0.4058 (15)	1.061 (2)	0.084 (7)
H1A	0.2380	0.3502	1.0205	0.126*
H1B	0.2322	0.4087	1.1687	0.126*
H1C	0.3292	0.4238	1.0738	0.126*
C2	0.1585 (17)	0.4606 (12)	0.934 (2)	0.066 (5)
H2A	0.1827	0.5174	0.9596	0.079*
H2B	0.0786	0.4540	0.9484	0.079*
C3	0.1491 (14)	0.4434 (15)	0.749 (2)	0.070 (6)
H3A	0.1203	0.3877	0.7212	0.084*
H3B	0.0896	0.4803	0.6767	0.084*
C4	0.3383 (15)	0.4013 (13)	0.6818 (18)	0.060 (5)
C5	0.3162 (16)	0.3112 (15)	0.681 (2)	0.081 (7)
H5A	0.2542	0.3001	0.7334	0.122*
H5B	0.3900	0.2838	0.7425	0.122*
H5C	0.2901	0.2917	0.5655	0.122*
C6	0.4485 (19)	0.4319 (17)	0.650 (3)	0.096 (8)
H6A	0.4451	0.4907	0.6420	0.144*
H6B	0.4547	0.4092	0.5458	0.144*
H6C	0.5184	0.4159	0.7423	0.144*
N	0.2647 (14)	0.4535 (10)	0.7133 (17)	0.065 (4)
H1	0.2878	0.5037	0.7134	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb	0.0404 (3)	0.0456 (4)	0.0332 (3)	−0.0002 (3)	0.0115 (2)	−0.0011 (2)
I1	0.0402 (6)	0.0678 (8)	0.0475 (5)	−0.0125 (5)	0.0120 (4)	−0.0054 (5)
I2	0.0368 (6)	0.0647 (8)	0.0538 (5)	0.0090 (5)	0.0069 (4)	0.0033 (5)
I3	0.0628 (7)	0.0412 (6)	0.0449 (5)	0.0028 (5)	0.0182 (4)	−0.0013 (4)
C1	0.073 (13)	0.11 (2)	0.079 (12)	0.040 (14)	0.045 (10)	−0.002 (12)
C2	0.060 (12)	0.057 (13)	0.090 (12)	−0.004 (9)	0.037 (9)	−0.015 (9)
C3	0.023 (8)	0.112 (17)	0.077 (10)	−0.004 (10)	0.019 (7)	−0.022 (11)
C4	0.054 (10)	0.082 (15)	0.048 (8)	0.026 (10)	0.023 (7)	0.012 (8)
C5	0.049 (12)	0.077 (18)	0.102 (15)	0.021 (11)	0.001 (10)	−0.018 (11)
C6	0.077 (15)	0.12 (2)	0.115 (16)	−0.003 (14)	0.057 (13)	0.038 (15)
N	0.070 (10)	0.057 (11)	0.068 (9)	0.005 (8)	0.021 (7)	0.016 (7)

Geometric parameters (Å, º)

Pb—I3	3.0974 (15)	C3—N	1.46 (2)
Pb—I1	3.1735 (14)	C3—H3A	0.9700
Pb—I2	3.2359 (17)	C3—H3B	0.9700
Pb—I1^i	3.2761 (17)	C4—N	1.28 (2)
Pb—I2^i	3.3605 (15)	C4—C6	1.46 (2)
Pb—I3^ii	3.4048 (17)	C4—C5	1.49 (3)
C1—C2	1.52 (3)	C5—H5A	0.9600
C1—H1A	0.9600	C5—H5B	0.9600
C1—H1B	0.9600	C5—H5C	0.9600
C1—H1C	0.9600	C6—H6A	0.9600
C2—C3	1.52 (2)	C6—H6B	0.9600
C2—H2A	0.9700	C6—H6C	0.9600
C2—H2B	0.9700	N—H1	0.8600
I3—Pb—I1	94.20 (4)	C1—C2—H2B	108.7
I3—Pb—I2	89.16 (4)	C3—C2—H2B	108.7
I1—Pb—I2	86.45 (4)	H2A—C2—H2B	107.6
I3—Pb—I1^i	85.63 (4)	N—C3—C2	113.0 (13)
I1—Pb—I1^i	94.56 (5)	N—C3—H3A	109.0
I2—Pb—I1^i	174.75 (3)	C2—C3—H3A	109.0
I3—Pb—I2^i	85.54 (4)	N—C3—H3B	109.0
I1—Pb—I2^i	177.37 (3)	C2—C3—H3B	109.0
I2—Pb—I2^i	96.17 (4)	H3A—C3—H3B	107.8
I1^i—Pb—I2^i	82.81 (4)	N—C4—C6	118 (2)
I3—Pb—I3^ii	171.33 (3)	N—C4—C5	122.1 (18)
I1—Pb—I3^ii	82.33 (4)	C6—C4—C5	119.5 (18)
I2—Pb—I3^ii	82.71 (4)	C4—C5—H5A	109.5
I1^i—Pb—I3^ii	102.53 (4)	C4—C5—H5B	109.5
I2^i—Pb—I3^ii	98.28 (4)	H5A—C5—H5B	109.5
Pb—I1—Pb^ii	79.52 (4)	C4—C5—H5C	109.5
Pb—I2—Pb^ii	77.41 (4)	H5A—C5—H5C	109.5
Pb—I3—Pb^i	78.61 (4)	H5B—C5—H5C	109.5
C2—C1—H1A	109.5	C4—C6—H6A	109.5
C2—C1—H1B	109.5	C4—C6—H6B	109.5
H1A—C1—H1B	109.5	H6A—C6—H6B	109.5
C2—C1—H1C	109.5	C4—C6—H6C	109.5
H1A—C1—H1C	109.5	H6A—C6—H6C	109.5
H1B—C1—H1C	109.5	H6B—C6—H6C	109.5
C1—C2—C3	114.2 (15)	C4—N—C3	132 (2)
C1—C2—H2A	108.7	C4—N—H1	114.0
C3—C2—H2A	108.7	C3—N—H1	114.0

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1···I2	0.86	3.09	3.882 (17)	155
N—H1···I3	0.86	3.25	3.702 (14)	116