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In the title compound, [Zn(C13H9N2O)2]·2C3H7NO, the ZnII ion is located on a twofold axis and chelated by two 2-(2-hydroxy­phen­yl)benzimidazole ligands with a distorted tetra­hedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028601/xu2069sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028601/xu2069Isup2.hkl
Contains datablock I

CCDC reference: 621538

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.069
  • Data-to-parameter ratio = 18.1

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C6 .. 6.42 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.02 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 0 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-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: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXTL-Plus.

Bis[2-(2-oxidophenyl)-1H-benzimidazole-κ2N3,O]zinc(II) dimethylformamide disolvate top
Crystal data top
[Zn(C13H9N2O)2]·2C3H7NOF(000) = 1312
Mr = 630.01Dx = 1.402 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 9896 reflections
a = 15.4137 (11) Åθ = 1.9–28.3°
b = 8.7799 (6) ŵ = 0.87 mm1
c = 22.0554 (15) ÅT = 293 K
V = 2984.8 (4) Å3Block, colorless
Z = 40.33 × 0.23 × 0.21 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3562 independent reflections
Radiation source: fine-focus sealed tube2229 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 1.9°
ω scansh = 1920
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 117
Tmin = 0.762, Tmax = 0.838l = 2826
17219 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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0281P)2]
where P = (Fo2 + 2Fc2)/3
3562 reflections(Δ/σ)max = 0.001
197 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.45 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*/Ueq
Zn10.00000.98535 (3)0.25000.03695 (10)
O10.09568 (8)1.08500 (13)0.28887 (5)0.0498 (3)
O20.01636 (10)0.69217 (17)0.53100 (6)0.0746 (4)
N10.03786 (9)0.87734 (14)0.32380 (5)0.0341 (3)
N20.03763 (9)0.79789 (15)0.41870 (5)0.0385 (3)
H2N0.02190.78560.45580.046*
N30.01009 (10)0.60406 (17)0.62514 (6)0.0496 (4)
C60.12138 (10)1.06913 (19)0.34534 (7)0.0392 (4)
C20.22531 (11)1.1502 (2)0.42209 (8)0.0543 (5)
H20.27361.20790.43260.065*
C30.18453 (12)1.0618 (2)0.46543 (8)0.0503 (5)
H30.20491.06040.50510.060*
C40.11403 (11)0.97666 (17)0.44931 (7)0.0428 (4)
H40.08720.91680.47860.051*
C50.08072 (10)0.97631 (17)0.39003 (7)0.0339 (4)
C10.19503 (11)1.1532 (2)0.36394 (8)0.0510 (5)
H10.22391.21270.33550.061*
C70.17375 (12)0.6367 (2)0.41370 (8)0.0496 (5)
H70.17430.60400.45380.059*
C80.23655 (12)0.5933 (2)0.37335 (8)0.0552 (5)
H80.28060.52910.38660.066*
C90.23701 (11)0.6420 (2)0.31301 (8)0.0510 (5)
H90.28080.60970.28700.061*
C100.17299 (11)0.73762 (19)0.29183 (7)0.0439 (4)
H100.17290.77120.25180.053*
C110.10860 (10)0.78228 (17)0.33208 (7)0.0337 (4)
C120.10913 (10)0.73184 (18)0.39160 (7)0.0366 (4)
C130.00351 (10)0.88526 (16)0.37704 (6)0.0320 (3)
C140.02758 (14)0.6205 (2)0.56724 (9)0.0624 (6)
H140.07750.57370.55260.075*
C150.06668 (16)0.5196 (2)0.66569 (10)0.0817 (7)
H15A0.11300.47440.64280.123*
H15B0.03400.44100.68560.123*
H15C0.09040.58750.69550.123*
C160.06428 (14)0.6768 (2)0.65172 (9)0.0728 (6)
H16A0.04560.74720.68230.109*
H16B0.10120.60120.66970.109*
H16C0.09580.73070.62090.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03888 (16)0.04666 (18)0.02532 (14)0.0000.00186 (13)0.000
O10.0501 (8)0.0690 (8)0.0304 (6)0.0192 (6)0.0023 (6)0.0007 (6)
O20.0880 (12)0.0908 (11)0.0450 (8)0.0005 (9)0.0038 (8)0.0226 (8)
N10.0352 (7)0.0405 (8)0.0265 (7)0.0020 (6)0.0012 (6)0.0006 (6)
N20.0429 (8)0.0484 (9)0.0243 (7)0.0066 (7)0.0038 (6)0.0031 (6)
N30.0588 (11)0.0524 (9)0.0376 (8)0.0035 (8)0.0062 (8)0.0018 (7)
C60.0341 (10)0.0440 (10)0.0395 (10)0.0000 (8)0.0029 (8)0.0100 (8)
C20.0375 (11)0.0617 (13)0.0638 (13)0.0076 (9)0.0085 (10)0.0172 (10)
C30.0473 (12)0.0587 (12)0.0447 (11)0.0027 (9)0.0158 (9)0.0082 (9)
C40.0466 (11)0.0453 (10)0.0365 (9)0.0001 (8)0.0075 (8)0.0003 (8)
C50.0327 (9)0.0368 (9)0.0322 (8)0.0012 (7)0.0017 (7)0.0052 (7)
C10.0402 (11)0.0596 (12)0.0532 (12)0.0108 (9)0.0049 (9)0.0065 (9)
C70.0522 (12)0.0560 (12)0.0405 (10)0.0125 (9)0.0003 (9)0.0078 (8)
C80.0490 (12)0.0604 (13)0.0563 (12)0.0183 (10)0.0003 (10)0.0039 (10)
C90.0422 (11)0.0598 (12)0.0510 (12)0.0104 (9)0.0072 (9)0.0031 (9)
C100.0452 (11)0.0528 (11)0.0336 (9)0.0035 (9)0.0059 (8)0.0004 (8)
C110.0341 (9)0.0357 (9)0.0312 (8)0.0003 (7)0.0008 (7)0.0011 (7)
C120.0369 (10)0.0400 (10)0.0329 (9)0.0008 (8)0.0017 (8)0.0011 (7)
C130.0352 (9)0.0353 (8)0.0255 (7)0.0039 (8)0.0017 (8)0.0019 (6)
C140.0685 (15)0.0675 (14)0.0512 (13)0.0072 (11)0.0156 (11)0.0026 (11)
C150.0955 (19)0.0802 (17)0.0694 (15)0.0012 (14)0.0137 (14)0.0156 (12)
C160.0730 (16)0.0779 (15)0.0674 (14)0.0102 (12)0.0197 (12)0.0138 (12)
Geometric parameters (Å, º) top
Zn1—O11.9171 (11)C4—C51.405 (2)
Zn1—O1i1.9171 (11)C4—H40.9300
Zn1—N1i1.9721 (12)C5—C131.462 (2)
Zn1—N11.9721 (12)C1—H10.9300
O1—C61.3144 (18)C7—C81.369 (2)
O2—C141.222 (2)C7—C121.389 (2)
N1—C131.3381 (18)C7—H70.9300
N1—C111.3852 (19)C8—C91.398 (2)
N2—C131.3545 (19)C8—H80.9300
N2—C121.3814 (19)C9—C101.377 (2)
N2—H2N0.8600C9—H90.9300
N3—C141.313 (2)C10—C111.388 (2)
N3—C161.437 (2)C10—H100.9300
N3—C151.453 (2)C11—C121.385 (2)
C6—C11.415 (2)C14—H140.9300
C6—C51.424 (2)C15—H15A0.9600
C2—C11.365 (2)C15—H15B0.9600
C2—C31.382 (2)C15—H15C0.9600
C2—H20.9300C16—H16A0.9600
C3—C41.366 (2)C16—H16B0.9600
C3—H30.9300C16—H16C0.9600
O1—Zn1—O1i125.70 (7)C8—C7—H7121.8
O1—Zn1—N1i111.15 (5)C12—C7—H7121.8
O1i—Zn1—N1i94.48 (5)C7—C8—C9122.53 (17)
O1—Zn1—N194.48 (5)C7—C8—H8118.7
O1i—Zn1—N1111.15 (5)C9—C8—H8118.7
N1i—Zn1—N1122.52 (7)C10—C9—C8120.38 (16)
C6—O1—Zn1127.38 (10)C10—C9—H9119.8
C13—N1—C11106.90 (12)C8—C9—H9119.8
C13—N1—Zn1123.94 (11)C9—C10—C11117.87 (16)
C11—N1—Zn1129.17 (10)C9—C10—H10121.1
C13—N2—C12108.53 (13)C11—C10—H10121.1
C13—N2—H2N125.7N1—C11—C12108.80 (13)
C12—N2—H2N125.7N1—C11—C10130.43 (14)
C14—N3—C16120.78 (17)C12—C11—C10120.76 (15)
C14—N3—C15122.10 (18)N2—C12—C11105.73 (13)
C16—N3—C15117.04 (17)N2—C12—C7132.30 (15)
O1—C6—C1117.47 (15)C11—C12—C7121.96 (15)
O1—C6—C5125.72 (14)N1—C13—N2110.04 (14)
C1—C6—C5116.80 (15)N1—C13—C5126.04 (14)
C1—C2—C3120.34 (17)N2—C13—C5123.91 (13)
C1—C2—H2119.8O2—C14—N3125.4 (2)
C3—C2—H2119.8O2—C14—H14117.3
C4—C3—C2119.27 (16)N3—C14—H14117.3
C4—C3—H3120.4N3—C15—H15A109.5
C2—C3—H3120.4N3—C15—H15B109.5
C3—C4—C5122.29 (17)H15A—C15—H15B109.5
C3—C4—H4118.9N3—C15—H15C109.5
C5—C4—H4118.9H15A—C15—H15C109.5
C4—C5—C6118.82 (15)H15B—C15—H15C109.5
C4—C5—C13118.75 (14)N3—C16—H16A109.5
C6—C5—C13122.38 (14)N3—C16—H16B109.5
C2—C1—C6122.45 (17)H16A—C16—H16B109.5
C2—C1—H1118.8N3—C16—H16C109.5
C6—C1—H1118.8H16A—C16—H16C109.5
C8—C7—C12116.49 (16)H16B—C16—H16C109.5
O1i—Zn1—O1—C6122.80 (14)Zn1—N1—C11—C12179.77 (11)
N1i—Zn1—O1—C6124.80 (13)C13—N1—C11—C10179.01 (16)
N1—Zn1—O1—C62.68 (14)Zn1—N1—C11—C100.9 (2)
O1—Zn1—N1—C132.49 (13)C9—C10—C11—N1179.21 (16)
O1i—Zn1—N1—C13133.63 (12)C9—C10—C11—C120.0 (2)
N1i—Zn1—N1—C13116.13 (13)C13—N2—C12—C110.45 (17)
O1—Zn1—N1—C11177.45 (13)C13—N2—C12—C7178.20 (18)
O1i—Zn1—N1—C1146.32 (14)N1—C11—C12—N20.11 (17)
N1i—Zn1—N1—C1163.92 (12)C10—C11—C12—N2179.48 (14)
Zn1—O1—C6—C1179.07 (12)N1—C11—C12—C7178.72 (15)
Zn1—O1—C6—C52.0 (2)C10—C11—C12—C70.6 (2)
C1—C2—C3—C40.5 (3)C8—C7—C12—N2179.31 (17)
C2—C3—C4—C50.5 (3)C8—C7—C12—C110.8 (3)
C3—C4—C5—C60.6 (2)C11—N1—C13—N20.57 (17)
C3—C4—C5—C13178.25 (15)Zn1—N1—C13—N2179.47 (10)
O1—C6—C5—C4177.27 (15)C11—N1—C13—C5178.20 (14)
C1—C6—C5—C41.7 (2)Zn1—N1—C13—C51.8 (2)
O1—C6—C5—C130.3 (3)C12—N2—C13—N10.65 (18)
C1—C6—C5—C13179.20 (14)C12—N2—C13—C5178.15 (14)
C3—C2—C1—C60.6 (3)C4—C5—C13—N1177.34 (15)
O1—C6—C1—C2177.32 (16)C6—C5—C13—N10.2 (2)
C5—C6—C1—C21.7 (3)C4—C5—C13—N21.3 (2)
C12—C7—C8—C90.4 (3)C6—C5—C13—N2178.81 (15)
C7—C8—C9—C100.2 (3)C16—N3—C14—O22.0 (3)
C8—C9—C10—C110.4 (3)C15—N3—C14—O2178.6 (2)
C13—N1—C11—C120.28 (17)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O20.861.942.7729 (18)162
 

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