In the title compound, {(C
18H
19N
4)[BiI
4]}
n, the organic cation is protonated on one of the two tertiary imino N atoms; the cation has inversion symmetry, involving disorder of this H atom. Adjacent cations are linked by a disordered N—H
N hydrogen bond, forming a chain that runs along the
a axis of the monoclinic unit cell. The anion exists as a polymeric chain that propogates along the
c axis; the Bi atom lies on a special position of site symmetry 2.
Supporting information
CCDC reference: 284277
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.009 Å
- R factor = 0.029
- wR factor = 0.070
- Data-to-parameter ratio = 22.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Bi1
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
Alert level G
ABSTM02_ALERT_3_G The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.072 0.322
Tmin(prime) and Tmax expected: 0.074 0.231
RR(prime) = 0.703
Please check that your absorption correction is appropriate.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
catena-Poly[
N-[4-(1
H-benzimidazol-3-yl)butyl]benzimidazolium [[diiodobismuthate(III)]-di-µ
2-iodo]]
top
Crystal data top
(C18H19N4)[BiI4] | F(000) = 1800 |
Mr = 1007.95 | Dx = 2.721 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 10565 reflections |
a = 19.900 (3) Å | θ = 3.2–27.5° |
b = 16.809 (2) Å | µ = 12.20 mm−1 |
c = 7.660 (2) Å | T = 291 K |
β = 106.23 (2)° | Prism, pink |
V = 2460.2 (8) Å3 | 0.20 × 0.18 × 0.12 mm |
Z = 4 | |
Data collection top
Rigaki R-AXIS RAPID IP diffractometer | 2806 independent reflections |
Radiation source: fine-focus sealed tube | 2608 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: numerical (NUMABS; Higashi, 1995) | h = −24→25 |
Tmin = 0.072, Tmax = 0.322 | k = −21→21 |
11767 measured reflections | l = −9→9 |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.070 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0311P)2 + 14.444P] where P = (Fo2 + 2Fc2)/3 |
2806 reflections | (Δ/σ)max = 0.001 |
123 parameters | Δρmax = 2.02 e Å−3 |
0 restraints | Δρmin = −1.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Bi1 | 0.5000 | 0.57513 (1) | 0.7500 | 0.0312 (1) | |
I1 | 0.40550 (2) | 0.56560 (2) | 1.00621 (5) | 0.0443 (1) | |
I2 | 0.41181 (3) | 0.69465 (3) | 0.51970 (6) | 0.0743 (2) | |
N1 | 0.0586 (2) | 0.6082 (3) | −0.1075 (8) | 0.056 (1) | |
N2 | 0.1536 (2) | 0.6600 (3) | 0.0797 (7) | 0.046 (1) | |
C1 | 0.2207 (3) | 0.5319 (4) | 0.1761 (8) | 0.048 (1) | |
C2 | 0.2131 (4) | 0.4515 (4) | 0.152 (1) | 0.059 (2) | |
C3 | 0.1520 (4) | 0.4182 (4) | 0.038 (1) | 0.061 (2) | |
C4 | 0.0966 (3) | 0.4646 (4) | −0.0557 (9) | 0.056 (2) | |
C5 | 0.1041 (3) | 0.5459 (4) | −0.0347 (8) | 0.045 (1) | |
C6 | 0.1648 (3) | 0.5788 (3) | 0.0830 (8) | 0.041 (1) | |
C7 | 0.0905 (3) | 0.6745 (4) | −0.0344 (9) | 0.052 (1) | |
C8 | 0.2031 (3) | 0.7195 (4) | 0.1801 (8) | 0.050 (1) | |
C9 | 0.2624 (3) | 0.7344 (4) | 0.0946 (7) | 0.047 (1) | |
H1n | 0.0180 | 0.6044 | −0.1846 | 0.067* | 0.50 |
H1 | 0.2614 | 0.5541 | 0.2512 | 0.057* | |
H2 | 0.2494 | 0.4182 | 0.2127 | 0.071* | |
H3 | 0.1488 | 0.3632 | 0.0253 | 0.073* | |
H4 | 0.0560 | 0.4421 | −0.1300 | 0.067* | |
H7 | 0.0712 | 0.7251 | −0.0596 | 0.063* | |
H8a | 0.2225 | 0.7015 | 0.3043 | 0.059* | |
H8b | 0.1784 | 0.7690 | 0.1835 | 0.059* | |
H9a | 0.2948 | 0.7723 | 0.1689 | 0.056* | |
H9b | 0.2875 | 0.6850 | 0.0937 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Bi1 | 0.0361 (1) | 0.0252 (1) | 0.0295 (1) | 0.000 | 0.0048 (1) | 0.000 |
I1 | 0.0425 (2) | 0.0481 (2) | 0.0446 (2) | 0.0165 (2) | 0.0161 (2) | 0.0110 (1) |
I2 | 0.0971 (4) | 0.0676 (3) | 0.0565 (3) | 0.0484 (3) | 0.0190 (2) | 0.0231 (2) |
N1 | 0.034 (2) | 0.055 (3) | 0.073 (3) | −0.001 (2) | 0.006 (2) | 0.002 (3) |
N2 | 0.039 (2) | 0.041 (3) | 0.056 (3) | −0.002 (2) | 0.007 (2) | −0.003 (2) |
C1 | 0.042 (3) | 0.046 (3) | 0.050 (3) | 0.001 (3) | 0.003 (2) | 0.003 (3) |
C2 | 0.059 (4) | 0.049 (4) | 0.060 (4) | 0.005 (3) | 0.002 (3) | 0.008 (3) |
C3 | 0.073 (4) | 0.041 (3) | 0.065 (4) | −0.007 (3) | 0.012 (4) | 0.002 (3) |
C4 | 0.053 (3) | 0.052 (4) | 0.056 (4) | −0.019 (3) | 0.006 (3) | −0.003 (3) |
C5 | 0.040 (3) | 0.047 (3) | 0.047 (3) | −0.007 (2) | 0.010 (2) | −0.001 (2) |
C6 | 0.040 (3) | 0.040 (3) | 0.044 (3) | −0.005 (2) | 0.011 (2) | −0.002 (2) |
C7 | 0.037 (3) | 0.043 (3) | 0.074 (4) | 0.005 (2) | 0.011 (3) | −0.001 (3) |
C8 | 0.053 (3) | 0.042 (3) | 0.052 (3) | −0.003 (3) | 0.012 (3) | −0.009 (3) |
C9 | 0.041 (3) | 0.044 (3) | 0.049 (3) | −0.005 (2) | 0.002 (2) | −0.001 (2) |
Geometric parameters (Å, º) top
Bi1—I1 | 3.0785 (7) | C4—C5 | 1.380 (9) |
Bi1—I1i | 3.0785 (7) | C5—C6 | 1.403 (8) |
Bi1—I1ii | 3.2645 (6) | C8—C9 | 1.521 (8) |
Bi1—I1iii | 3.2645 (6) | C9—C9iv | 1.49 (1) |
Bi1—I2 | 2.9151 (6) | N1—H1n | 0.86 |
Bi1—I2i | 2.9151 (6) | C1—H1 | 0.93 |
N1—C7 | 1.326 (8) | C2—H2 | 0.93 |
N1—C5 | 1.394 (8) | C3—H3 | 0.93 |
N2—C7 | 1.337 (7) | C4—H4 | 0.93 |
N2—C6 | 1.383 (7) | C7—H7 | 0.93 |
N2—C8 | 1.462 (7) | C8—H8a | 0.97 |
C1—C2 | 1.366 (9) | C8—H8b | 0.97 |
C1—C6 | 1.387 (8) | C9—H9a | 0.97 |
C2—C3 | 1.40 (1) | C9—H9b | 0.97 |
C3—C4 | 1.38 (1) | | |
| | | |
I1—Bi1—I1i | 174.03 (2) | N2—C6—C5 | 105.7 (5) |
I1—Bi1—I1ii | 87.39 (2) | C1—C6—C5 | 122.0 (5) |
I1—Bi1—I1iii | 88.29 (2) | N1—C7—N2 | 111.9 (5) |
I1—Bi1—I2 | 92.87 (2) | N2—C8—C9 | 112.1 (5) |
I1—Bi1—I2i | 91.25 (2) | C9iv—C9—C8 | 113.1 (6) |
I1i—Bi1—I1ii | 88.29 (2) | C7—N1—H1n | 126.8 |
I1i—Bi1—I1iii | 87.39 (2) | C5—N1—H1n | 126.8 |
I1i—Bi1—I2 | 91.25 (2) | C2—C1—H1 | 121.6 |
I1i—Bi1—I2i | 92.87 (2) | C6—C1—H1 | 121.6 |
I1ii—Bi1—I1iii | 87.13 (2) | C1—C2—H2 | 119.2 |
I1ii—Bi1—I2 | 177.11 (1) | C3—C2—H2 | 119.2 |
I1ii—Bi1—I2i | 90.00 (2) | C4—C3—H3 | 119.1 |
I1iii—Bi1—I2 | 90.00 (2) | C2—C3—H3 | 119.1 |
I1iii—Bi1—I2i | 177.11 (1) | C3—C4—H4 | 121.4 |
I2—Bi1—I2i | 92.87 (3) | C5—C4—H4 | 121.4 |
Bi1—I1—Bi1ii | 92.61 (2) | N1—C7—H7 | 124.0 |
C7—N1—C5 | 106.4 (5) | N2—C7—H7 | 124.0 |
C7—N2—C6 | 108.0 (5) | N2—C8—H8a | 109.2 |
C7—N2—C8 | 126.2 (5) | C9—C8—H8a | 109.2 |
C6—N2—C8 | 125.7 (5) | N2—C8—H8b | 109.2 |
C2—C1—C6 | 116.7 (6) | C9—C8—H8b | 109.2 |
C1—C2—C3 | 121.6 (6) | H8a—C8—H8b | 107.9 |
C4—C3—C2 | 121.8 (6) | C9iv—C9—H9a | 109.0 |
C3—C4—C5 | 117.1 (6) | C8—C9—H9a | 109.0 |
C4—C5—N1 | 131.4 (6) | C9iv—C9—H9b | 109.0 |
C4—C5—C6 | 120.7 (6) | C8—C9—H9b | 109.0 |
N1—C5—C6 | 107.9 (5) | H9a—C9—H9b | 107.8 |
N2—C6—C1 | 132.3 (5) | | |
| | | |
I2i—Bi1—I1—Bi1ii | −89.94 (2) | C8—N2—C6—C5 | −179.2 (5) |
I2—Bi1—I1—Bi1ii | 177.12 (2) | C2—C1—C6—N2 | 177.7 (6) |
I1iii—Bi1—I1—Bi1ii | 87.20 (2) | C2—C1—C6—C5 | −1.8 (9) |
C6—C1—C2—C3 | 0 (1) | C4—C5—C6—N2 | −176.7 (6) |
C1—C2—C3—C4 | 0 (1) | N1—C5—C6—N2 | 0.9 (6) |
C2—C3—C4—C5 | 1 (1) | C4—C5—C6—C1 | 2.9 (9) |
C3—C4—C5—N1 | −179.3 (6) | N1—C5—C6—C1 | −179.4 (6) |
C3—C4—C5—C6 | −2 (1) | C5—N1—C7—N2 | 0.5 (7) |
C7—N1—C5—C4 | 176.5 (7) | C6—N2—C7—N1 | 0.1 (7) |
C7—N1—C5—C6 | −0.9 (7) | C8—N2—C7—N1 | 178.6 (5) |
C7—N2—C6—C1 | 179.8 (6) | C7—N2—C8—C9 | −102.8 (7) |
C8—N2—C6—C1 | 1 (1) | C6—N2—C8—C9 | 75.4 (7) |
C7—N2—C6—C5 | −0.7 (7) | N2—C8—C9—C9iv | 61.3 (8) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) x, −y+1, z−1/2; (iv) −x+1/2, −y+3/2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···N1v | 0.86 | 1.87 | 2.71 (1) | 165 |
Symmetry code: (v) −x, y, −z−1/2. |