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The crystal structure of the title iodo­antimonate complex, 4,4′-bipyridinium(2+) di-μ-iodo-bis­[(4,4′-bipyridyl)­tri­iodo­anti­mony(III)], formulated as [4,4′-H2bipy]2+[Sb2I8(4,4′-bipy)2]2− or (C10H10N2)[Sb2I8(C10H8N2)2], contains layers of hydrogen-bonded ribbon polymers in which anionic dimetal complexes are linked through hydrogen bonding with 4,4′-H2bipy cations. The complex is isostructural with its bismuth analogue.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022347/br6118sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022347/br6118Isup2.hkl
Contains datablock I

CCDC reference: 226647

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.041
  • wR factor = 0.079
  • Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT432_ALERT_2_A Short Inter X...Y Contact C1' .. C2' = 2.83 Ang.
Author Response: This contact is between two atoms that both have partial occupancies of less than 50%.

Alert level B CHEMW01_ALERT_1_B The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.95 <> 1.05 Calculated formula weight = 1729.3115 Formula weight given = 1629.2600 CHEMW03_ALERT_2_B WARNING: The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.95 <> 1.05 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_weight 1629.26 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 30.00 360.33 H 1.01 26.00 26.21 N 14.01 6.00 84.04 Sb 121.75 2.00 243.50 I 126.90 8.00 1015.24 Calculated formula weight 1729.32 DENSD01_ALERT_1_B The ratio of the submitted crystal density and that calculated from the formula is outside the range 0.95 <> 1.05 Crystal density given = 2.608 Calculated crystal density = 2.457 PLAT043_ALERT_1_B Check Reported Molecular Weight ................ 1629.26 PLAT046_ALERT_1_B Reported Z, MW and D(calc) are Inconsistent .... 2.46 PLAT432_ALERT_2_B Short Inter X...Y Contact C2' .. C2' = 3.02 Ang.
Author Response: This contact is between two atoms that both have partial occupancies of less than 50%.

Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.528 0.710 Tmin and Tmax expected: 0.449 0.710 RR = 1.175 Please check that your absorption correction is appropriate. CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.19 PLAT213_ALERT_2_C Atom C2' has ADP max/min Ratio ............. 3.30 prolat PLAT213_ALERT_2_C Atom C5' has ADP max/min Ratio ............. 3.30 prolat PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C1' PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C4' PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C3 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C13 PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.37 PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.82 PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C10 H10 N2
1 ALERT level A = In general: serious problem 6 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL (Siemens, 1996); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4,4'-bipyridinium(2+) di-µ-iodo-bis[(4,4'-bipyridyl)triiodoantimony(III)] top
Crystal data top
(C10H8N)[Sb2I8(C10H8N2)2]F(000) = 1548
Mr = 1629.26Dx = 2.608 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5693 reflections
a = 9.6444 (19) Åθ = 2–27°
b = 12.678 (2) ŵ = 6.86 mm1
c = 18.097 (2) ÅT = 173 K
β = 95.570 (16)°Block, orange
V = 2202.3 (6) Å30.20 × 0.10 × 0.05 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
5038 independent reflections
Radiation source: fine-focus sealed tube3230 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 8.192 pixels mm-1θmax = 27.5°, θmin = 2.0°
Frames, each covering 0.3° in ω scansh = 125
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1516
Tmin = 0.528, Tmax = 0.710l = 2323
13744 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0291P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
5038 reflectionsΔρmax = 1.35 e Å3
234 parametersΔρmin = 1.56 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00028 (5)
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.3904 (13)0.7885 (10)0.4554 (7)0.045 (4)0.659 (11)
H10.30670.76490.47360.054*0.659 (11)
C20.3837 (13)0.8477 (9)0.3923 (7)0.041 (4)0.659 (11)
H20.29620.86290.36570.049*0.659 (11)
C1'0.483 (4)0.872 (2)0.4949 (15)0.079 (9)0.341 (11)
H1'0.46460.90370.54050.095*0.341 (11)
C2'0.476 (3)0.932 (2)0.4313 (14)0.067 (9)0.341 (11)
H2'0.44671.00390.43230.080*0.341 (11)
C30.5127 (8)0.8878 (6)0.3659 (4)0.0357 (18)
C40.6268 (13)0.8487 (12)0.4027 (8)0.050 (4)0.659 (11)
H40.71370.86130.38370.061*0.659 (11)
C50.6258 (15)0.7900 (12)0.4678 (8)0.047 (4)0.659 (11)
H50.71220.77040.49370.056*0.659 (11)
C4'0.574 (4)0.799 (2)0.3654 (16)0.079 (9)0.341 (11)
H4'0.60880.77180.32180.095*0.341 (11)
C5'0.588 (4)0.743 (2)0.4339 (16)0.067 (9)0.341 (11)
H5'0.65380.68640.43850.080*0.341 (11)
C60.3932 (9)1.0762 (6)0.2124 (4)0.041 (2)
H60.31451.11920.19790.049*
C70.3950 (8)1.0165 (6)0.2759 (4)0.0374 (19)
H70.31811.01890.30490.045*
C80.5072 (8)0.9534 (6)0.2976 (4)0.0330 (18)
C90.6159 (9)0.9530 (7)0.2535 (4)0.047 (2)
H90.69560.91040.26640.057*
C100.6084 (10)1.0147 (7)0.1904 (5)0.054 (2)
H100.68381.01380.16030.065*
N10.5164 (8)0.7625 (5)0.4931 (4)0.0454 (18)
N20.4993 (7)1.0750 (5)0.1708 (3)0.0368 (16)
Sb10.51916 (5)0.62082 (4)0.59623 (3)0.03187 (14)
I10.32731 (6)0.75800 (4)0.66135 (3)0.04248 (15)
I20.26512 (6)0.51266 (4)0.49351 (3)0.04121 (15)
I30.76038 (6)0.72265 (4)0.66929 (3)0.04023 (15)
I40.50347 (6)0.45484 (5)0.70763 (3)0.05013 (18)
C110.4969 (10)1.2577 (7)0.0049 (5)0.052 (2)
H110.49691.19720.02610.063*
C120.4971 (9)1.3563 (6)0.0272 (5)0.048 (2)
H120.49651.36260.07960.057*
C130.4983 (8)1.4463 (6)0.0163 (4)0.0386 (19)
C140.4958 (12)1.4304 (7)0.0915 (5)0.069 (3)
H140.49391.48950.12370.082*
C150.4959 (12)1.3307 (8)0.1206 (5)0.074 (3)
H150.49531.32300.17280.089*
N30.4968 (8)1.2442 (6)0.0790 (4)0.059 (2)
H30.49731.18090.09890.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.032 (7)0.066 (10)0.037 (7)0.001 (7)0.006 (6)0.023 (7)
C20.040 (7)0.037 (8)0.045 (7)0.007 (6)0.006 (6)0.015 (6)
C1'0.17 (3)0.037 (12)0.036 (11)0.031 (15)0.028 (14)0.002 (9)
C2'0.12 (2)0.046 (13)0.042 (12)0.046 (14)0.045 (13)0.030 (10)
C30.035 (4)0.035 (5)0.037 (4)0.008 (4)0.001 (4)0.001 (4)
C40.029 (7)0.061 (10)0.062 (10)0.007 (7)0.012 (7)0.033 (8)
C50.033 (8)0.064 (11)0.042 (8)0.000 (7)0.002 (7)0.009 (7)
C4'0.17 (3)0.037 (12)0.036 (11)0.031 (15)0.028 (14)0.002 (9)
C5'0.12 (2)0.046 (13)0.042 (12)0.046 (14)0.045 (13)0.030 (10)
C60.049 (5)0.033 (4)0.040 (5)0.009 (4)0.002 (4)0.006 (4)
C70.039 (5)0.034 (4)0.038 (4)0.002 (4)0.000 (4)0.008 (4)
C80.041 (5)0.028 (4)0.029 (4)0.004 (4)0.003 (4)0.000 (3)
C90.045 (5)0.065 (6)0.033 (4)0.013 (5)0.004 (4)0.014 (4)
C100.050 (5)0.077 (7)0.039 (5)0.007 (5)0.017 (4)0.001 (5)
N10.056 (5)0.048 (4)0.033 (4)0.014 (4)0.004 (4)0.004 (3)
N20.040 (4)0.039 (4)0.031 (4)0.002 (3)0.000 (3)0.002 (3)
Sb10.0387 (3)0.0343 (3)0.0220 (2)0.0001 (2)0.0001 (2)0.0004 (2)
I10.0436 (3)0.0458 (3)0.0382 (3)0.0017 (3)0.0044 (2)0.0080 (2)
I20.0432 (3)0.0464 (3)0.0327 (3)0.0038 (3)0.0029 (2)0.0106 (2)
I30.0435 (3)0.0378 (3)0.0380 (3)0.0052 (3)0.0033 (2)0.0037 (2)
I40.0458 (3)0.0664 (4)0.0374 (3)0.0049 (3)0.0002 (3)0.0195 (3)
C110.073 (6)0.041 (5)0.045 (5)0.002 (5)0.013 (5)0.010 (4)
C120.064 (6)0.047 (5)0.034 (4)0.003 (5)0.015 (4)0.004 (4)
C130.047 (5)0.039 (5)0.030 (4)0.000 (4)0.007 (4)0.007 (4)
C140.128 (10)0.046 (6)0.031 (5)0.017 (6)0.004 (6)0.010 (4)
C150.131 (10)0.062 (7)0.028 (5)0.014 (7)0.002 (6)0.003 (5)
N30.082 (6)0.047 (5)0.047 (5)0.006 (4)0.004 (4)0.011 (4)
Geometric parameters (Å, º) top
C1—C21.362 (15)C7—H70.9500
C1—N11.375 (13)C8—C91.379 (11)
C1—H10.9500C9—C101.380 (11)
C2—C31.466 (14)C9—H90.9500
C2—H20.9500C10—N21.321 (10)
C1'—C2'1.38 (3)C10—H100.9500
C1'—N11.43 (2)Sb1—N12.588 (7)
C1'—H1'0.9500Sb1—I32.8687 (8)
C2'—C31.39 (3)Sb1—I12.8741 (8)
C2'—H2'0.9500Sb1—I42.9283 (8)
C3—C4'1.27 (3)Sb1—I23.2334 (9)
C3—C41.326 (14)Sb1—I2i3.2381 (9)
C3—C81.486 (10)I2—Sb1i3.2381 (9)
C4—C51.393 (18)C11—N31.352 (10)
C4—H40.9500C11—C121.378 (10)
C5—N11.241 (15)C11—H110.9500
C5—H50.9500C12—C131.386 (10)
C4'—C5'1.43 (4)C12—H120.9500
C4'—H4'0.9500C13—C141.379 (10)
C5'—N11.36 (3)C13—C13ii1.486 (14)
C5'—H5'0.9500C14—C151.368 (12)
C6—N21.327 (10)C14—H140.9500
C6—C71.376 (10)C15—N31.331 (11)
C6—H60.9500C15—H150.9500
C7—C81.371 (10)N3—H30.8800
C2—C1—N1121.1 (11)C9—C10—H10119.1
C2—C1—H1119.5C5—N1—C1119.4 (10)
N1—C1—H1119.5C5'—N1—C1'109.5 (17)
C1—C2—C3119.4 (10)C5—N1—Sb1120.8 (8)
C1—C2—H2120.3C5'—N1—Sb1118.0 (11)
C3—C2—H2120.3C1—N1—Sb1118.1 (7)
C2'—C1'—N1121 (2)C1'—N1—Sb1130.2 (11)
C2'—C1'—H1'119.5C10—N2—C6119.5 (7)
N1—C1'—H1'119.5C10—N2—H3123.8
C1'—C2'—C3119 (2)C6—N2—H3115.5
C1'—C2'—H2'120.3N1—Sb1—I388.35 (16)
C3—C2'—H2'120.3N1—Sb1—I185.05 (16)
C4'—C3—C2'121.6 (17)I3—Sb1—I193.68 (2)
C4—C3—C2113.3 (9)N1—Sb1—I4175.90 (17)
C4'—C3—C8117.9 (15)I3—Sb1—I495.73 (2)
C4—C3—C8126.0 (9)I1—Sb1—I494.25 (2)
C2'—C3—C8119.3 (11)N1—Sb1—I285.73 (16)
C2—C3—C8120.1 (7)I3—Sb1—I2172.38 (2)
C3—C4—C5123.4 (12)I1—Sb1—I290.59 (2)
C3—C4—H4118.3I4—Sb1—I290.24 (2)
C5—C4—H4118.3N1—Sb1—I2i87.90 (16)
N1—C5—C4122.6 (12)I3—Sb1—I2i86.25 (2)
N1—C5—H5118.7I1—Sb1—I2i172.95 (2)
C4—C5—H5118.7I4—Sb1—I2i92.77 (2)
C3—C4'—C5'116 (2)I2—Sb1—I2i88.74 (2)
C3—C4'—H4'121.9Sb1—I2—Sb1i91.26 (2)
C5'—C4'—H4'121.9N3—C11—C12122.2 (8)
N1—C5'—C4'125 (3)N3—C11—H11118.9
N1—C5'—H5'117.3C12—C11—H11118.9
C4'—C5'—H5'117.3C11—C12—C13120.5 (8)
N2—C6—C7121.3 (7)C11—C12—H12119.8
N2—C6—H6119.4C13—C12—H12119.8
C7—C6—H6119.4C14—C13—C12116.2 (7)
C8—C7—C6120.4 (8)C14—C13—C13ii122.0 (9)
C8—C7—H7119.8C12—C13—C13ii121.8 (9)
C6—C7—H7119.8C15—C14—C13121.0 (9)
C7—C8—C9117.3 (7)C15—C14—H14119.5
C7—C8—C3121.9 (7)C13—C14—H14119.5
C9—C8—C3120.8 (7)N3—C15—C14122.9 (9)
C8—C9—C10119.7 (8)N3—C15—H15118.6
C8—C9—H9120.1C14—C15—H15118.6
C10—C9—H9120.1C15—N3—C11117.2 (8)
N2—C10—C9121.7 (8)C15—N3—H3121.4
N2—C10—H10119.1C11—N3—H3121.4
N1—C1—C2—C32.5 (19)C4'—C5'—N1—Sb1165 (3)
N1—C1'—C2'—C35 (5)C2—C1—N1—C52.7 (19)
C1'—C2'—C3—C4'12 (5)C2—C1—N1—C5'40 (2)
C1'—C2'—C3—C447 (3)C2—C1—N1—C1'67.7 (17)
C1'—C2'—C3—C269 (3)C2—C1—N1—Sb1168.2 (10)
C1'—C2'—C3—C8179 (3)C2'—C1'—N1—C557 (3)
C1—C2—C3—C4'53.3 (19)C2'—C1'—N1—C5'23 (4)
C1—C2—C3—C48.7 (17)C2'—C1'—N1—C167 (3)
C1—C2—C3—C2'68.9 (16)C2'—C1'—N1—Sb1174 (2)
C1—C2—C3—C8179.4 (10)C9—C10—N2—C60.4 (13)
C4'—C3—C4—C586 (3)C9—C10—N2—H3166.4
C2'—C3—C4—C551 (2)C7—C6—N2—C100.5 (12)
C2—C3—C4—C510 (2)C7—C6—N2—H3167.4
C8—C3—C4—C5178.1 (12)C5—N1—Sb1—I343.6 (10)
C3—C4—C5—N16 (3)C5'—N1—Sb1—I390 (2)
C4—C3—C4'—C5'60 (3)C1—N1—Sb1—I3151.2 (8)
C2'—C3—C4'—C5'7 (5)C1'—N1—Sb1—I371 (2)
C2—C3—C4'—C5'57 (4)C5—N1—Sb1—I1137.4 (10)
C8—C3—C4'—C5'175 (3)C5'—N1—Sb1—I1176 (2)
C3—C4'—C5'—N116 (6)C1—N1—Sb1—I157.3 (8)
N2—C6—C7—C80.3 (12)C1'—N1—Sb1—I123 (2)
C6—C7—C8—C90.1 (11)C5—N1—Sb1—I2131.6 (10)
C6—C7—C8—C3180.0 (7)C5'—N1—Sb1—I285 (2)
C4'—C3—C8—C7146 (2)C1—N1—Sb1—I233.6 (8)
C4—C3—C8—C7159.8 (11)C1'—N1—Sb1—I2114 (2)
C2'—C3—C8—C746.4 (19)C5—N1—Sb1—I2i42.7 (10)
C2—C3—C8—C729.3 (12)C5'—N1—Sb1—I2i4 (2)
C4'—C3—C8—C934 (2)C1—N1—Sb1—I2i122.5 (8)
C4—C3—C8—C920.2 (15)C1'—N1—Sb1—I2i157 (2)
C2'—C3—C8—C9133.5 (18)N1—Sb1—I2—Sb1i87.99 (16)
C2—C3—C8—C9150.7 (9)I1—Sb1—I2—Sb1i172.98 (2)
C7—C8—C9—C100.1 (12)I4—Sb1—I2—Sb1i92.77 (2)
C3—C8—C9—C10179.9 (8)I2i—Sb1—I2—Sb1i0.0
C8—C9—C10—N20.1 (14)N3—C11—C12—C130.5 (14)
C4—C5—N1—C5'68 (2)C11—C12—C13—C141.6 (13)
C4—C5—N1—C11 (2)C11—C12—C13—C13ii178.7 (10)
C4—C5—N1—C1'57.9 (19)C12—C13—C14—C151.7 (15)
C4—C5—N1—Sb1166.4 (11)C13ii—C13—C14—C15178.5 (11)
C4'—C5'—N1—C589 (4)C13—C14—C15—N30.8 (18)
C4'—C5'—N1—C137 (4)C14—C15—N3—C110.3 (16)
C4'—C5'—N1—C1'30 (5)C12—C11—N3—C150.5 (15)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+3, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N20.881.872.71 (2)160
 

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