Download citation
Download citation
link to html
In the title compound, [Zn(C7H6N2)2(C4H4O5)], one oxydi­acetate dianion and two benz­imidazole mol­ecules coordinate to the ZnII atom in distorted trigonal-bipyramidal coordination geometry. The interplanar distance of 3.422 (4) Å between parallel benz­imidazole rings of neighbouring mol­ecules indicates the existence of π–π stacking.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804019488/hb6076sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804019488/hb6076Isup2.hkl
Contains datablock I

CCDC reference: 251590

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.027
  • wR factor = 0.070
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(1H-benzimidazole-κN3)(oxydiacetato-κ3O,O',O'')zinc(II) top
Crystal data top
[Zn(C7H6N2)2(C4H4O5)]F(000) = 1776
Mr = 433.72Dx = 1.598 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6382 reflections
a = 25.049 (6) Åθ = 2.4–25.5°
b = 7.0568 (18) ŵ = 1.40 mm1
c = 21.420 (5) ÅT = 295 K
β = 107.783 (3)°Prism, colourless
V = 3605.4 (15) Å30.32 × 0.28 × 0.22 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3258 independent reflections
Radiation source: fine-focus sealed tube2883 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 10.00 pixels mm-1θmax = 25.2°, θmin = 1.7°
ω scansh = 3017
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 88
Tmin = 0.648, Tmax = 0.737l = 2525
7413 measured reflections
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0367P)2 + 2.2003P]
where P = (Fo2 + 2Fc2)/3
3258 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.27 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)
Zn0.363701 (9)0.02472 (3)0.134771 (11)0.03246 (9)
O10.39367 (7)0.2767 (2)0.17818 (7)0.0493 (4)
O20.41049 (8)0.4574 (2)0.26737 (8)0.0598 (5)
O3A0.3535 (3)0.0040 (11)0.2281 (4)0.0480 (18)0.42
O3B0.3308 (2)0.0459 (9)0.2140 (3)0.0425 (12)0.58
O40.31510 (6)0.2170 (2)0.13018 (6)0.0399 (3)
O50.26946 (7)0.4015 (2)0.18119 (7)0.0470 (4)
N110.50045 (8)0.3332 (3)0.15737 (9)0.0497 (5)
H110.51680.44010.16950.060*
N130.43682 (7)0.1073 (2)0.14148 (8)0.0380 (4)
N210.27846 (7)0.0731 (3)0.06353 (9)0.0394 (4)
H210.25790.02120.09910.047*
N230.32499 (7)0.1079 (2)0.04178 (8)0.0325 (4)
C10.39004 (9)0.3166 (3)0.23424 (10)0.0409 (5)
C20.35733 (12)0.1822 (3)0.26321 (11)0.0564 (7)
H2A0.37630.16380.30960.068*0.42
H2B0.32020.23240.25810.068*0.42
H2C0.38140.13270.30450.068*0.58
H2D0.32600.24720.27140.068*0.58
C30.31420 (10)0.1310 (3)0.23705 (10)0.0454 (5)
H3A0.28120.06690.24110.055*0.42
H3B0.33070.20370.27670.055*0.42
H3C0.28130.09740.24950.055*0.58
H3D0.34100.19240.27400.055*0.58
C40.29830 (8)0.2607 (3)0.17813 (9)0.0337 (4)
C120.45212 (9)0.2774 (3)0.16551 (10)0.0442 (5)
H120.43150.35080.18590.053*
C140.48670 (9)0.1244 (3)0.08802 (11)0.0460 (5)
H140.46090.22260.08270.055*
C150.53354 (10)0.1421 (4)0.06749 (12)0.0555 (6)
H150.53960.25520.04840.067*
C160.57183 (11)0.0041 (4)0.07461 (14)0.0576 (7)
H160.60230.01230.05890.069*
C170.56624 (9)0.1727 (4)0.10418 (12)0.0534 (6)
H170.59220.27010.10920.064*
C180.51949 (9)0.1896 (3)0.12618 (10)0.0407 (5)
C190.47949 (8)0.0463 (3)0.11704 (10)0.0370 (5)
C220.29323 (8)0.0037 (3)0.00387 (11)0.0374 (5)
H220.28220.12420.00470.045*
C240.35998 (9)0.4402 (3)0.03192 (11)0.0380 (5)
H240.37880.45750.07620.046*
C250.35913 (10)0.5794 (3)0.01365 (11)0.0456 (5)
H250.37840.69210.00030.055*
C260.33023 (10)0.5555 (3)0.07988 (12)0.0489 (6)
H260.33070.65270.10900.059*
C270.30112 (10)0.3929 (3)0.10336 (11)0.0451 (5)
H270.28160.37790.14760.054*
C280.30224 (8)0.2511 (3)0.05779 (10)0.0337 (4)
C290.33146 (8)0.2731 (3)0.00873 (9)0.0303 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.03580 (15)0.03087 (14)0.03296 (14)0.00427 (10)0.01386 (10)0.00040 (9)
O10.0679 (10)0.0391 (9)0.0444 (9)0.0189 (8)0.0227 (8)0.0066 (7)
O20.0767 (12)0.0445 (9)0.0515 (10)0.0274 (9)0.0098 (9)0.0135 (8)
O3A0.072 (5)0.036 (4)0.044 (4)0.029 (3)0.031 (4)0.014 (3)
O3B0.059 (3)0.038 (3)0.036 (2)0.020 (2)0.022 (2)0.0109 (17)
O40.0496 (9)0.0368 (8)0.0367 (8)0.0138 (7)0.0182 (7)0.0059 (6)
O50.0569 (10)0.0434 (9)0.0413 (8)0.0222 (8)0.0161 (7)0.0022 (7)
N110.0481 (11)0.0379 (10)0.0562 (12)0.0097 (9)0.0056 (9)0.0104 (9)
N130.0361 (9)0.0355 (9)0.0419 (10)0.0009 (8)0.0114 (8)0.0051 (8)
N210.0357 (9)0.0414 (10)0.0375 (10)0.0015 (8)0.0057 (7)0.0079 (8)
N230.0343 (9)0.0285 (8)0.0349 (9)0.0022 (7)0.0106 (7)0.0004 (7)
C10.0467 (12)0.0346 (11)0.0364 (11)0.0085 (9)0.0051 (9)0.0016 (9)
C20.0846 (18)0.0468 (14)0.0412 (12)0.0279 (13)0.0243 (12)0.0187 (10)
C30.0619 (14)0.0429 (13)0.0365 (11)0.0223 (11)0.0225 (10)0.0049 (9)
C40.0325 (10)0.0333 (11)0.0344 (10)0.0035 (9)0.0088 (8)0.0023 (8)
C120.0459 (13)0.0402 (12)0.0429 (12)0.0025 (10)0.0079 (10)0.0086 (10)
C140.0419 (12)0.0405 (12)0.0572 (14)0.0045 (10)0.0176 (11)0.0102 (10)
C150.0477 (14)0.0575 (16)0.0648 (16)0.0056 (12)0.0224 (12)0.0103 (12)
C160.0417 (13)0.0703 (18)0.0664 (17)0.0040 (12)0.0248 (12)0.0021 (13)
C170.0341 (12)0.0617 (16)0.0616 (15)0.0097 (11)0.0104 (11)0.0087 (12)
C180.0362 (11)0.0380 (12)0.0424 (12)0.0040 (9)0.0039 (9)0.0012 (9)
C190.0320 (10)0.0392 (11)0.0384 (11)0.0009 (9)0.0086 (9)0.0016 (9)
C220.0348 (11)0.0317 (11)0.0471 (12)0.0027 (9)0.0145 (9)0.0023 (9)
C240.0413 (12)0.0311 (11)0.0404 (11)0.0013 (9)0.0108 (9)0.0011 (9)
C250.0507 (13)0.0327 (11)0.0568 (14)0.0008 (10)0.0213 (11)0.0027 (10)
C260.0568 (14)0.0404 (13)0.0554 (15)0.0102 (11)0.0256 (12)0.0167 (11)
C270.0485 (13)0.0516 (14)0.0352 (11)0.0154 (11)0.0128 (10)0.0070 (10)
C280.0292 (10)0.0353 (11)0.0376 (10)0.0056 (8)0.0119 (8)0.0015 (9)
C290.0278 (10)0.0291 (10)0.0353 (10)0.0038 (8)0.0114 (8)0.0003 (8)
Geometric parameters (Å, º) top
Zn—N132.0205 (18)C2—H2C0.9700
Zn—N232.0181 (16)C2—H2D0.9700
Zn—O12.0406 (15)C3—H3A0.9700
Zn—O3A2.098 (9)C3—H3B0.9700
Zn—O3B2.105 (6)C3—H3C0.9700
Zn—O42.0807 (14)C3—H3D0.9700
O1—C11.264 (2)C12—H120.9300
O2—C11.237 (2)C14—C151.379 (3)
O3A—C21.453 (9)C14—C191.393 (3)
O3A—C31.424 (9)C14—H140.9300
O3B—C21.433 (7)C15—C161.385 (4)
O3B—C31.449 (7)C15—H150.9300
C1—C21.505 (3)C16—C171.375 (4)
C3—C41.511 (3)C16—H160.9300
O4—C41.261 (2)C17—C181.394 (3)
O5—C41.241 (2)C17—H170.9300
N11—C121.334 (3)C18—C191.395 (3)
N11—C181.377 (3)C22—H220.9300
N11—H110.8600C24—C251.381 (3)
N13—C121.316 (3)C24—C291.389 (3)
N13—C191.394 (3)C24—H240.9300
N21—C221.332 (3)C25—C261.392 (3)
N21—C281.380 (3)C25—H250.9300
N21—H210.8600C26—C271.371 (3)
N23—C221.317 (3)C26—H260.9300
N23—C291.399 (2)C27—C281.392 (3)
C2—H2A0.9700C27—H270.9300
C2—H2B0.9700C28—C291.397 (3)
N23—Zn—N13110.87 (7)O3B—C2—C1107.9 (3)
N23—Zn—O1101.26 (6)O3B—C3—C4105.5 (3)
N13—Zn—O199.80 (7)O3B—C2—H2C116.6
N23—Zn—O495.40 (6)O3B—C2—H2D103.4
N13—Zn—O497.45 (7)O3B—C3—H3C103.9
O1—Zn—O4149.84 (6)O3B—C3—H3D117.6
N23—Zn—O3A143.09 (18)H3A—C3—H3B108.4
N13—Zn—O3A105.79 (18)H3C—C3—H3D108.7
O1—Zn—O3A76.2 (2)O5—C4—O4125.64 (19)
O4—Zn—O3A75.4 (2)O5—C4—C3116.75 (17)
N23—Zn—O3B125.90 (12)O4—C4—C3117.61 (17)
N13—Zn—O3B123.00 (12)N13—C12—N11112.7 (2)
O1—Zn—O3B75.59 (18)N13—C12—H12123.7
O4—Zn—O3B74.27 (18)N11—C12—H12123.7
C1—O1—Zn120.27 (13)C15—C14—C19117.4 (2)
C3—O3A—C2116.7 (6)C15—C14—H14121.3
C3—O3A—Zn117.7 (5)C19—C14—H14121.3
C2—O3A—Zn115.1 (5)C14—C15—C16121.7 (2)
C2—O3B—C3116.4 (4)C14—C15—H15119.2
C2—O3B—Zn115.7 (4)C16—C15—H15119.2
C3—O3B—Zn116.0 (4)C17—C16—C15122.1 (2)
C4—O4—Zn119.86 (12)C17—C16—H16119.0
C12—N11—C18107.99 (18)C15—C16—H16119.0
C12—N11—H11126.0C16—C17—C18116.4 (2)
C18—N11—H11126.0C16—C17—H17121.8
C12—N13—C19105.27 (18)C18—C17—H17121.8
C12—N13—Zn126.72 (15)N11—C18—C17132.7 (2)
C19—N13—Zn127.81 (14)N11—C18—C19105.16 (19)
C22—N21—C28107.39 (17)C17—C18—C19122.1 (2)
C22—N21—H21126.3C14—C19—C18120.3 (2)
C28—N21—H21126.3C14—C19—N13130.82 (19)
C22—N23—C29105.05 (16)C18—C19—N13108.87 (18)
C22—N23—Zn123.92 (14)N23—C22—N21113.38 (18)
C29—N23—Zn130.32 (13)N23—C22—H22123.3
O2—C1—O1125.9 (2)N21—C22—H22123.3
O2—C1—C2116.8 (2)C25—C24—C29117.1 (2)
O1—C1—C2117.23 (18)C25—C24—H24121.4
C1—C2—H2A110.3C29—C24—H24121.4
C1—C2—H2B110.3C24—C25—C26121.7 (2)
C1—C2—H2C109.8C24—C25—H25119.2
C1—C2—H2D110.4C26—C25—H25119.2
C4—C3—H3A110.1C27—C26—C25121.9 (2)
C4—C3—H3B110.1C27—C26—H26119.1
C4—C3—H3C110.3C25—C26—H26119.1
C4—C3—H3D110.6C26—C27—C28116.8 (2)
O3A—C2—C1106.9 (4)C26—C27—H27121.6
O3A—C3—C4108.1 (4)C28—C27—H27121.6
O3A—C2—H2A110.3N21—C28—C27132.5 (2)
O3A—C2—H2B110.3N21—C28—C29105.63 (17)
O3A—C3—H3A110.1C27—C28—C29121.82 (19)
O3A—C3—H3B110.1C24—C29—C28120.72 (18)
H2A—C2—H2B108.6C24—C29—N23130.74 (18)
H2C—C2—H2D108.4C28—C29—N23108.54 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O2i0.862.042.750 (3)139
N21—H21···O5ii0.861.882.722 (2)165
Symmetry codes: (i) x+1, y1, z+1/2; (ii) x+1/2, y1/2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds