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In the title compound, {(C18H19N4)[BiI4]}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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805035804/hb6302sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805035804/hb6302Isup2.hkl
Contains datablock I

CCDC reference: 284277

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](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

Computing details top

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-(1H-benzimidazol-3-yl)butyl]benzimidazolium [[diiodobismuthate(III)]-di-µ2-iodo]] top
Crystal data top
(C18H19N4)[BiI4]F(000) = 1800
Mr = 1007.95Dx = 2.721 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 10565 reflections
a = 19.900 (3) Åθ = 3.2–27.5°
b = 16.809 (2) ŵ = 12.20 mm1
c = 7.660 (2) ÅT = 291 K
β = 106.23 (2)°Prism, pink
V = 2460.2 (8) Å30.20 × 0.18 × 0.12 mm
Z = 4
Data collection top
Rigaki R-AXIS RAPID IP
diffractometer
2806 independent reflections
Radiation source: fine-focus sealed tube2608 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: numerical
(NUMABS; Higashi, 1995)
h = 2425
Tmin = 0.072, Tmax = 0.322k = 2121
11767 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-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 parametersΔρmax = 2.02 e Å3
0 restraintsΔρmin = 1.22 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Bi10.50000.57513 (1)0.75000.0312 (1)
I10.40550 (2)0.56560 (2)1.00621 (5)0.0443 (1)
I20.41181 (3)0.69465 (3)0.51970 (6)0.0743 (2)
N10.0586 (2)0.6082 (3)0.1075 (8)0.056 (1)
N20.1536 (2)0.6600 (3)0.0797 (7)0.046 (1)
C10.2207 (3)0.5319 (4)0.1761 (8)0.048 (1)
C20.2131 (4)0.4515 (4)0.152 (1)0.059 (2)
C30.1520 (4)0.4182 (4)0.038 (1)0.061 (2)
C40.0966 (3)0.4646 (4)0.0557 (9)0.056 (2)
C50.1041 (3)0.5459 (4)0.0347 (8)0.045 (1)
C60.1648 (3)0.5788 (3)0.0830 (8)0.041 (1)
C70.0905 (3)0.6745 (4)0.0344 (9)0.052 (1)
C80.2031 (3)0.7195 (4)0.1801 (8)0.050 (1)
C90.2624 (3)0.7344 (4)0.0946 (7)0.047 (1)
H1n0.01800.60440.18460.067*0.50
H10.26140.55410.25120.057*
H20.24940.41820.21270.071*
H30.14880.36320.02530.073*
H40.05600.44210.13000.067*
H70.07120.72510.05960.063*
H8a0.22250.70150.30430.059*
H8b0.17840.76900.18350.059*
H9a0.29480.77230.16890.056*
H9b0.28750.68500.09370.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Bi10.0361 (1)0.0252 (1)0.0295 (1)0.0000.0048 (1)0.000
I10.0425 (2)0.0481 (2)0.0446 (2)0.0165 (2)0.0161 (2)0.0110 (1)
I20.0971 (4)0.0676 (3)0.0565 (3)0.0484 (3)0.0190 (2)0.0231 (2)
N10.034 (2)0.055 (3)0.073 (3)0.001 (2)0.006 (2)0.002 (3)
N20.039 (2)0.041 (3)0.056 (3)0.002 (2)0.007 (2)0.003 (2)
C10.042 (3)0.046 (3)0.050 (3)0.001 (3)0.003 (2)0.003 (3)
C20.059 (4)0.049 (4)0.060 (4)0.005 (3)0.002 (3)0.008 (3)
C30.073 (4)0.041 (3)0.065 (4)0.007 (3)0.012 (4)0.002 (3)
C40.053 (3)0.052 (4)0.056 (4)0.019 (3)0.006 (3)0.003 (3)
C50.040 (3)0.047 (3)0.047 (3)0.007 (2)0.010 (2)0.001 (2)
C60.040 (3)0.040 (3)0.044 (3)0.005 (2)0.011 (2)0.002 (2)
C70.037 (3)0.043 (3)0.074 (4)0.005 (2)0.011 (3)0.001 (3)
C80.053 (3)0.042 (3)0.052 (3)0.003 (3)0.012 (3)0.009 (3)
C90.041 (3)0.044 (3)0.049 (3)0.005 (2)0.002 (2)0.001 (2)
Geometric parameters (Å, º) top
Bi1—I13.0785 (7)C4—C51.380 (9)
Bi1—I1i3.0785 (7)C5—C61.403 (8)
Bi1—I1ii3.2645 (6)C8—C91.521 (8)
Bi1—I1iii3.2645 (6)C9—C9iv1.49 (1)
Bi1—I22.9151 (6)N1—H1n0.86
Bi1—I2i2.9151 (6)C1—H10.93
N1—C71.326 (8)C2—H20.93
N1—C51.394 (8)C3—H30.93
N2—C71.337 (7)C4—H40.93
N2—C61.383 (7)C7—H70.93
N2—C81.462 (7)C8—H8a0.97
C1—C21.366 (9)C8—H8b0.97
C1—C61.387 (8)C9—H9a0.97
C2—C31.40 (1)C9—H9b0.97
C3—C41.38 (1)
I1—Bi1—I1i174.03 (2)N2—C6—C5105.7 (5)
I1—Bi1—I1ii87.39 (2)C1—C6—C5122.0 (5)
I1—Bi1—I1iii88.29 (2)N1—C7—N2111.9 (5)
I1—Bi1—I292.87 (2)N2—C8—C9112.1 (5)
I1—Bi1—I2i91.25 (2)C9iv—C9—C8113.1 (6)
I1i—Bi1—I1ii88.29 (2)C7—N1—H1n126.8
I1i—Bi1—I1iii87.39 (2)C5—N1—H1n126.8
I1i—Bi1—I291.25 (2)C2—C1—H1121.6
I1i—Bi1—I2i92.87 (2)C6—C1—H1121.6
I1ii—Bi1—I1iii87.13 (2)C1—C2—H2119.2
I1ii—Bi1—I2177.11 (1)C3—C2—H2119.2
I1ii—Bi1—I2i90.00 (2)C4—C3—H3119.1
I1iii—Bi1—I290.00 (2)C2—C3—H3119.1
I1iii—Bi1—I2i177.11 (1)C3—C4—H4121.4
I2—Bi1—I2i92.87 (3)C5—C4—H4121.4
Bi1—I1—Bi1ii92.61 (2)N1—C7—H7124.0
C7—N1—C5106.4 (5)N2—C7—H7124.0
C7—N2—C6108.0 (5)N2—C8—H8a109.2
C7—N2—C8126.2 (5)C9—C8—H8a109.2
C6—N2—C8125.7 (5)N2—C8—H8b109.2
C2—C1—C6116.7 (6)C9—C8—H8b109.2
C1—C2—C3121.6 (6)H8a—C8—H8b107.9
C4—C3—C2121.8 (6)C9iv—C9—H9a109.0
C3—C4—C5117.1 (6)C8—C9—H9a109.0
C4—C5—N1131.4 (6)C9iv—C9—H9b109.0
C4—C5—C6120.7 (6)C8—C9—H9b109.0
N1—C5—C6107.9 (5)H9a—C9—H9b107.8
N2—C6—C1132.3 (5)
I2i—Bi1—I1—Bi1ii89.94 (2)C8—N2—C6—C5179.2 (5)
I2—Bi1—I1—Bi1ii177.12 (2)C2—C1—C6—N2177.7 (6)
I1iii—Bi1—I1—Bi1ii87.20 (2)C2—C1—C6—C51.8 (9)
C6—C1—C2—C30 (1)C4—C5—C6—N2176.7 (6)
C1—C2—C3—C40 (1)N1—C5—C6—N20.9 (6)
C2—C3—C4—C51 (1)C4—C5—C6—C12.9 (9)
C3—C4—C5—N1179.3 (6)N1—C5—C6—C1179.4 (6)
C3—C4—C5—C62 (1)C5—N1—C7—N20.5 (7)
C7—N1—C5—C4176.5 (7)C6—N2—C7—N10.1 (7)
C7—N1—C5—C60.9 (7)C8—N2—C7—N1178.6 (5)
C7—N2—C6—C1179.8 (6)C7—N2—C8—C9102.8 (7)
C8—N2—C6—C11 (1)C6—N2—C8—C975.4 (7)
C7—N2—C6—C50.7 (7)N2—C8—C9—C9iv61.3 (8)
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+1, y+1, z+2; (iii) x, y+1, z1/2; (iv) x+1/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···N1v0.861.872.71 (1)165
Symmetry code: (v) x, y, z1/2.
 

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