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In the title compound, {[Zn2(C10H2O8)(C7H6N2)4]·H2O}n, the ZnII atom has a distorted tetra­hedral geometry, defined by two N atoms from two benzimidazole ligands and two O atoms from two benzene-1,2,4,5-tetra­carboxyl­ate (btc) tetra-anions. The complete btc anion is generated by inversion symmetry. The polymeric structure exhibits one-dimensional double chains running along the [100] direction, which further extend into a three-dimensional supra­molecular network by way of π–π stacking involving the benzimidazole rings. A non-coordinated water mol­ecule completes the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603515X/hb2127sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603515X/hb2127Isup2.hkl
Contains datablock I

CCDC reference: 624542

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • H-atom completeness 93%
  • Disorder in solvent or counterion
  • R factor = 0.026
  • wR factor = 0.071
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 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 ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C38 H28 N8 O9 Zn2 Atom count from _chemical_formula_moiety:C38 H28 N8 O3 Zn2 FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C38 H28 N8 O9 Zn2 Atom count from the _atom_site data: C38 H26 N8 O9 Zn2 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C38 H28 N8 O9 Zn2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 152.00 152.00 0.00 H 112.00 104.00 8.00 N 32.00 32.00 0.00 O 36.00 36.00 0.00 Zn 8.00 8.00 0.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 9 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

catena-poly[[bis[bis(1H-benzimidazole-κN3)zinc(II)]-µ4– benzene-1,2,4,5-tetracarboxylato] monohydrate] top
Crystal data top
[Zn2(C10H2O8)(C7H6N2)4]·H2OF(000) = 1776
Mr = 871.42Dx = 1.618 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 10890 reflections
a = 21.848 (8) Åθ = 1.9–28.3°
b = 11.057 (5) ŵ = 1.41 mm1
c = 14.806 (6) ÅT = 295 K
β = 90.288 (15)°Block, colorless
V = 3577 (2) Å30.35 × 0.27 × 0.22 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
4355 independent reflections
Radiation source: fine-focus sealed tube3911 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 2828
Tmin = 0.639, Tmax = 0.732k = 149
10890 measured reflectionsl = 1919
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0396P)2 + 2.1651P]
where P = (Fo2 + 2Fc2)/3
4355 reflections(Δ/σ)max = 0.039
262 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.52 e Å3
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)
Zn10.399878 (7)0.197417 (14)0.246520 (10)0.02117 (6)
C10.41583 (7)0.07719 (13)0.26650 (10)0.0262 (3)
C20.39901 (9)0.09311 (17)0.35638 (12)0.0381 (4)
H2A0.39010.02760.39350.046*
C30.39612 (11)0.21046 (19)0.38785 (15)0.0513 (5)
H3A0.38540.22470.44760.062*
C40.40910 (12)0.30870 (18)0.33105 (17)0.0549 (6)
H4A0.40620.38660.35430.066*
C50.42588 (10)0.29412 (15)0.24251 (15)0.0437 (5)
H5A0.43430.35990.20550.052*
C60.42964 (7)0.17545 (14)0.21100 (12)0.0297 (3)
C70.44160 (7)0.00630 (14)0.13624 (10)0.0291 (3)
H7A0.45020.04690.08930.035*
C80.28554 (7)0.28454 (15)0.34248 (11)0.0283 (3)
C90.30566 (8)0.40068 (16)0.36243 (12)0.0359 (4)
H9A0.34270.42980.34080.043*
C100.26820 (10)0.4711 (2)0.41576 (14)0.0474 (5)
H10A0.28030.54930.43060.057*
C110.21223 (10)0.4268 (2)0.44796 (14)0.0512 (5)
H11A0.18810.47660.48370.061*
C120.19208 (9)0.3124 (2)0.42849 (13)0.0458 (5)
H12A0.15520.28330.45070.055*
C130.22941 (7)0.24183 (18)0.37389 (11)0.0347 (4)
C140.27538 (8)0.10072 (16)0.29508 (12)0.0357 (4)
H14A0.28290.02690.26720.043*
C150.53989 (6)0.28234 (13)0.09368 (9)0.0215 (3)
C160.51575 (6)0.39205 (12)0.04411 (9)0.0193 (3)
C170.45781 (6)0.44254 (12)0.05698 (9)0.0199 (3)
C180.41015 (6)0.38366 (13)0.11610 (9)0.0220 (3)
C190.44305 (6)0.54984 (12)0.01292 (9)0.0216 (3)
H19A0.40460.58380.02180.026*
N10.42350 (6)0.02881 (11)0.21688 (8)0.0261 (3)
N20.44627 (6)0.12634 (12)0.12898 (9)0.0315 (3)
H2B0.45760.16580.08190.038*
N30.31392 (6)0.19282 (12)0.29319 (9)0.0293 (3)
N40.22446 (7)0.12502 (15)0.34136 (10)0.0398 (3)
H4B0.19410.07670.34940.048*
O10.55202 (5)0.30165 (10)0.17605 (7)0.0298 (2)
O20.55052 (6)0.18816 (10)0.05167 (8)0.0362 (3)
O30.41761 (5)0.27092 (9)0.12948 (7)0.0250 (2)
O40.36790 (6)0.44538 (11)0.14671 (9)0.0413 (3)
O1W0.2567 (4)0.3070 (7)0.0931 (6)0.177 (3)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02730 (10)0.01792 (9)0.01833 (10)0.00480 (6)0.00349 (6)0.00094 (6)
C10.0308 (7)0.0203 (7)0.0276 (7)0.0015 (6)0.0016 (6)0.0023 (6)
C20.0474 (10)0.0359 (9)0.0310 (8)0.0021 (8)0.0036 (7)0.0051 (7)
C30.0641 (14)0.0477 (12)0.0422 (11)0.0100 (10)0.0007 (10)0.0202 (9)
C40.0670 (15)0.0303 (10)0.0674 (15)0.0109 (9)0.0110 (11)0.0201 (9)
C50.0502 (12)0.0217 (8)0.0590 (12)0.0020 (7)0.0104 (9)0.0005 (7)
C60.0306 (8)0.0224 (7)0.0361 (9)0.0013 (6)0.0044 (6)0.0023 (6)
C70.0342 (8)0.0274 (8)0.0256 (7)0.0023 (6)0.0031 (6)0.0016 (6)
C80.0253 (7)0.0339 (8)0.0258 (7)0.0002 (6)0.0019 (6)0.0023 (6)
C90.0344 (9)0.0341 (9)0.0393 (9)0.0012 (7)0.0050 (7)0.0022 (7)
C100.0509 (11)0.0422 (11)0.0489 (11)0.0096 (9)0.0022 (9)0.0098 (9)
C110.0427 (11)0.0694 (15)0.0416 (11)0.0212 (10)0.0075 (8)0.0056 (10)
C120.0270 (9)0.0706 (15)0.0399 (10)0.0070 (8)0.0068 (7)0.0076 (9)
C130.0246 (8)0.0476 (10)0.0320 (8)0.0023 (7)0.0005 (6)0.0072 (7)
C140.0329 (8)0.0359 (9)0.0384 (9)0.0103 (7)0.0006 (7)0.0000 (7)
C150.0228 (7)0.0204 (6)0.0214 (7)0.0035 (5)0.0062 (5)0.0064 (5)
C160.0250 (7)0.0172 (6)0.0158 (6)0.0022 (5)0.0016 (5)0.0024 (5)
C170.0230 (6)0.0183 (6)0.0183 (6)0.0000 (5)0.0036 (5)0.0023 (5)
C180.0228 (7)0.0225 (7)0.0209 (6)0.0007 (5)0.0033 (5)0.0035 (5)
C190.0221 (6)0.0204 (7)0.0222 (7)0.0050 (5)0.0040 (5)0.0036 (5)
N10.0354 (7)0.0199 (6)0.0231 (6)0.0011 (5)0.0037 (5)0.0004 (5)
N20.0346 (7)0.0284 (7)0.0316 (7)0.0021 (5)0.0027 (5)0.0090 (5)
N30.0280 (7)0.0294 (7)0.0306 (7)0.0066 (5)0.0042 (5)0.0012 (5)
N40.0271 (7)0.0465 (9)0.0458 (9)0.0150 (6)0.0022 (6)0.0052 (7)
O10.0379 (6)0.0310 (6)0.0205 (5)0.0105 (4)0.0006 (4)0.0047 (4)
O20.0568 (8)0.0225 (6)0.0293 (6)0.0134 (5)0.0060 (5)0.0020 (4)
O30.0340 (6)0.0193 (5)0.0217 (5)0.0017 (4)0.0059 (4)0.0034 (4)
O40.0376 (6)0.0320 (6)0.0546 (8)0.0100 (5)0.0255 (6)0.0136 (6)
O1W0.133 (6)0.183 (8)0.216 (8)0.055 (5)0.050 (5)0.060 (6)
Geometric parameters (Å, º) top
Zn1—O1i1.9325 (11)C10—C111.403 (3)
Zn1—O31.9545 (11)C10—H10A0.9300
Zn1—N11.9842 (15)C11—C121.369 (3)
Zn1—N32.0049 (14)C11—H11A0.9300
C1—N11.3939 (19)C12—C131.391 (3)
C1—C21.393 (2)C12—H12A0.9300
C1—C61.396 (2)C13—N41.382 (3)
C2—C31.380 (3)C14—N31.322 (2)
C2—H2A0.9300C14—N41.337 (2)
C3—C41.403 (3)C14—H14A0.9300
C3—H3A0.9300C15—O21.2356 (18)
C4—C51.372 (3)C15—O11.2648 (19)
C4—H4A0.9300C15—C161.5115 (19)
C5—C61.395 (2)C16—C19ii1.3941 (19)
C5—H5A0.9300C16—C171.3974 (19)
C6—N21.381 (2)C17—C191.3911 (19)
C7—N11.318 (2)C17—C181.5112 (19)
C7—N21.336 (2)C18—O41.2358 (18)
C7—H7A0.9300C18—O31.2726 (18)
C8—C91.389 (2)C19—C16ii1.3941 (19)
C8—C131.396 (2)C19—H19A0.9300
C8—N31.397 (2)N2—H2B0.8600
C9—C101.381 (3)N4—H4B0.8600
C9—H9A0.9300O1—Zn1i1.9325 (11)
O1i—Zn1—O399.69 (5)C11—C12—C13116.87 (18)
O1i—Zn1—N1123.39 (6)C11—C12—H12A121.6
O3—Zn1—N198.14 (5)C13—C12—H12A121.6
O1i—Zn1—N3108.55 (5)N4—C13—C12132.98 (17)
O3—Zn1—N3120.41 (5)N4—C13—C8105.51 (15)
N1—Zn1—N3107.31 (5)C12—C13—C8121.48 (18)
N1—C1—C2129.99 (15)N3—C14—N4112.82 (16)
N1—C1—C6108.49 (14)N3—C14—H14A123.6
C2—C1—C6121.51 (15)N4—C14—H14A123.6
C3—C2—C1117.00 (18)O2—C15—O1126.06 (13)
C3—C2—H2A121.5O2—C15—C16119.87 (13)
C1—C2—H2A121.5O1—C15—C16113.80 (12)
C2—C3—C4121.0 (2)C19ii—C16—C17119.11 (12)
C2—C3—H3A119.5C19ii—C16—C15116.05 (12)
C4—C3—H3A119.5C17—C16—C15124.65 (12)
C5—C4—C3122.49 (17)C19—C17—C16119.00 (12)
C5—C4—H4A118.8C19—C17—C18118.70 (12)
C3—C4—H4A118.8C16—C17—C18122.29 (12)
C4—C5—C6116.51 (18)O4—C18—O3125.38 (13)
C4—C5—H5A121.7O4—C18—C17119.52 (13)
C6—C5—H5A121.7O3—C18—C17115.10 (12)
N2—C6—C5132.86 (17)C17—C19—C16ii121.89 (13)
N2—C6—C1105.68 (14)C17—C19—H19A119.1
C5—C6—C1121.45 (17)C16ii—C19—H19A119.1
N1—C7—N2112.89 (14)C7—N1—C1105.50 (13)
N1—C7—H7A123.6C7—N1—Zn1123.83 (11)
N2—C7—H7A123.6C1—N1—Zn1129.89 (10)
C9—C8—C13121.32 (16)C7—N2—C6107.43 (13)
C9—C8—N3129.92 (15)C7—N2—H2B126.3
C13—C8—N3108.75 (15)C6—N2—H2B126.3
C10—C9—C8117.08 (17)C14—N3—C8105.30 (14)
C10—C9—H9A121.5C14—N3—Zn1128.66 (12)
C8—C9—H9A121.5C8—N3—Zn1125.51 (10)
C9—C10—C11121.2 (2)C14—N4—C13107.60 (14)
C9—C10—H10A119.4C14—N4—H4B126.2
C11—C10—H10A119.4C13—N4—H4B126.2
C12—C11—C10122.07 (18)C15—O1—Zn1i125.59 (10)
C12—C11—H11A119.0C18—O3—Zn1121.31 (9)
C10—C11—H11A119.0
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1, y+1, z.
 

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