Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024087/lh2386sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024087/lh2386Isup2.hkl |
CCDC reference: 646091
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.016 Å
- Disorder in solvent or counterion
- R factor = 0.068
- wR factor = 0.244
- Data-to-parameter ratio = 16.3
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 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.12 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C28 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N8 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 42.00 Perc. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 16 PLAT602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure ! PLAT722_ALERT_1_C Angle Calc 124.00, Rep 125.40 Dev... 1.40 Deg. N8 -C28 -H28 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.70 Deg. O2 -CL1 -O2' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 32.90 Deg. O4' -CL1 -O4 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 31.90 Deg. O3 -CL1 -O3' 1.555 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.946 Tmax scaled 0.575 Tmin scaled 0.509 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 251
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 20 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature see: Pandey et al., 1992; Addison et al., 1981; Wu et al., 2006; Athimoolam et al. (2005); Cox et al. (2003); Mohamed et al. (2003); Spek (2003); Stähler et al. (2001).
To a stired solution of tris(N-methylbenzimidazol-2-ylmethyl)amine (0.0899 g, 0.2 mmol) in hot MeOH (10 ml) was added Zn(ClO4)2.6(H2O) (0.0745 g, 0.2 mmol), followed by a solution of sodium iodide (0.0301 g, 0.2 mmol) in MeOH (5 ml). A colorless crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to form a colorless solution that was allowed to evaporate at room temperature. Colorless crystals suitable for X-ray diffraction studies were obtained after one week. Yield, 0.101 g (65%). (found: C, 44.32; H, 3.77; N,13.58; Zn, 8.23. Calcd. for C28.5 H30.5 Cl I N7.5 0O4.50 Zn: C, 44.01; H, 3.95; N, 13.51; Cu, 8.41%)
H atoms were placed in calculated positions, with C—H distances ranging from 0.93 to 0.97 Å, and treated as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. The Atoms O2/O3/O4 of the perchlorate anion are disordered over two sites with refined occupancies 0.562 (17):0.438 (17). The highest peak of 1.18 e A°-3 is 3.72Å from H27B. The SQUEEZE option in PLATON (Spek, 2003) indicated there was a solvent cavity of volume 599 Å3 containing approximately 90 electrons (possibly additional disordered DMF). In the final cycles of refinement, this contribution to the electron density was removed from the observed data. The density, the F(000) value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered solvent molecules were carried out by Stähler et al. (2001), Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005).
The asymmetric unit of the title compound, (Fig. 1), consists of a [Zn(Mentb)(I)] cation, a perchlorate anion and half a DMF molecule. The perchlorate anions is disordered and the DMF solvent is half occupancy. The ZnII ion is five-coordinate with a N4I ligand set. The Mentb ligand acts as a tetradentate N-donor, and an iodide completes the coordination. The coordination geometry of the ZnII may be best described as trigonal-bipyramidal, with approximate C3 molecular site symmetry. This geometry is assumed by the ZnII to relieve the steric crowding. The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the ZnII atom protrudes towards I and is 0.563 (5) Å from the plane of atoms N2/N4/N6. The axial sites are occupyied by N1 and I1, with Zn1—N1 2.442 (5) Å, Zn1—I1 2.6148 (10) Å and N1—Zn1—I1 is 179.50 (13)°. The three benzimidazole ring arms of the Mentb ligand form a cone-shaped cavity. The angles N2—Zn1—N6, N2—Zn1—N4 and N4—Zn1—N6 are 115.2 (2), 110.7 (2) and 112.9 (2) °, respectively. The N1—Zn1—N2 74.6 (2), N1—Zn1—N4 73.9 (2) and N1—Zn1—N6, 74.2 (2)° angles, which are all ca 16 ° less than the ideal value of 90°, are imposed by the geometry of the Mentb ligand. The bond angles and distance in the three benzimidazole groups are equal within experimental error. In the crystal structure, there are weak π···π stacking interactions with a centroid···centroid distance of 3.542 (6)Å bewteen inversion related molecules (see Fig. 2). Some references related to the title compound are Pandey et al. (1992), Addison et al. (1981) & Wu et al., (2006).
For related literature see: Pandey et al., 1992; Addison et al., 1981; Wu et al., 2006; Athimoolam et al. (2005); Cox et al. (2003); Mohamed et al. (2003); Spek (2003); Stähler et al. (2001).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1996); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[ZnI(C27H27N7)]ClO4·0.5C3H7NO | Z = 2 |
Mr = 777.82 | F(000) = 780 |
Triclinic, P1 | Dx = 1.229 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.743 (2) Å | Cell parameters from 3637 reflections |
b = 14.399 (3) Å | θ = 2.2–23.8° |
c = 14.554 (3) Å | µ = 1.42 mm−1 |
α = 97.562 (2)° | T = 298 K |
β = 112.766 (2)° | Block, colourless |
γ = 114.420 (2)° | 0.50 × 0.42 × 0.39 mm |
V = 2102.7 (7) Å3 |
Bruker SMART CCD diffractometer | 7231 independent reflections |
Radiation source: fine-focus sealed tube | 4303 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −15→11 |
Tmin = 0.537, Tmax = 0.608 | k = −17→16 |
10873 measured reflections | l = −17→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.245 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1343P)2 + 1.7701P] where P = (Fo2 + 2Fc2)/3 |
7231 reflections | (Δ/σ)max < 0.001 |
443 parameters | Δρmax = 1.18 e Å−3 |
251 restraints | Δρmin = −0.56 e Å−3 |
[ZnI(C27H27N7)]ClO4·0.5C3H7NO | γ = 114.420 (2)° |
Mr = 777.82 | V = 2102.7 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.743 (2) Å | Mo Kα radiation |
b = 14.399 (3) Å | µ = 1.42 mm−1 |
c = 14.554 (3) Å | T = 298 K |
α = 97.562 (2)° | 0.50 × 0.42 × 0.39 mm |
β = 112.766 (2)° |
Bruker SMART CCD diffractometer | 7231 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 4303 reflections with I > 2σ(I) |
Tmin = 0.537, Tmax = 0.608 | Rint = 0.020 |
10873 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 251 restraints |
wR(F2) = 0.245 | H-atom parameters constrained |
S = 1.09 | Δρmax = 1.18 e Å−3 |
7231 reflections | Δρmin = −0.56 e Å−3 |
443 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.17757 (8) | 0.33681 (6) | 0.18237 (6) | 0.0481 (3) | |
I1 | 0.01595 (6) | 0.30635 (5) | 0.25900 (5) | 0.0818 (3) | |
Cl1 | 0.3784 (3) | 0.2727 (2) | 0.8325 (2) | 0.0851 (7) | |
N1 | 0.3298 (5) | 0.3651 (4) | 0.1122 (4) | 0.0413 (12) | |
N2 | 0.1770 (6) | 0.1913 (5) | 0.1515 (5) | 0.0513 (14) | |
N3 | 0.2031 (7) | 0.0727 (5) | 0.0621 (6) | 0.0651 (18) | |
N4 | 0.0976 (6) | 0.3644 (5) | 0.0429 (5) | 0.0544 (15) | |
N5 | 0.1150 (8) | 0.4303 (5) | −0.0832 (5) | 0.0645 (18) | |
N6 | 0.3567 (6) | 0.4701 (5) | 0.2979 (5) | 0.0512 (14) | |
N7 | 0.5753 (6) | 0.5621 (5) | 0.3815 (5) | 0.0620 (17) | |
N8 | 0.605 (3) | 0.132 (2) | 0.163 (2) | 0.185 (8) | 0.50 |
O1 | 0.4358 (8) | 0.2947 (6) | 0.7669 (6) | 0.112 (2) | |
O2 | 0.2766 (19) | 0.1658 (11) | 0.7939 (17) | 0.129 (6) | 0.438 (17) |
O3 | 0.4796 (17) | 0.293 (2) | 0.9358 (12) | 0.121 (5) | 0.438 (17) |
O4 | 0.338 (2) | 0.3502 (16) | 0.8425 (17) | 0.111 (5) | 0.438 (17) |
O2' | 0.344 (2) | 0.1694 (10) | 0.8390 (15) | 0.126 (5) | 0.562 (17) |
O3' | 0.4773 (15) | 0.3486 (14) | 0.9443 (9) | 0.127 (5) | 0.562 (17) |
O4' | 0.2711 (15) | 0.2913 (17) | 0.8095 (13) | 0.114 (4) | 0.562 (17) |
O5 | 0.539 (2) | 0.2270 (18) | 0.2079 (14) | 0.150 (6) | 0.50 |
C1 | 0.2863 (9) | 0.2584 (6) | 0.0460 (7) | 0.065 (2) | |
H1A | 0.3614 | 0.2561 | 0.0463 | 0.077* | |
H1B | 0.2241 | 0.2435 | −0.0266 | 0.077* | |
C2 | 0.3133 (8) | 0.4366 (6) | 0.0547 (7) | 0.062 (2) | |
H2A | 0.3392 | 0.4294 | 0.0008 | 0.074* | |
H2B | 0.3698 | 0.5114 | 0.1030 | 0.074* | |
C3 | 0.4577 (8) | 0.4139 (7) | 0.2062 (7) | 0.065 (2) | |
H3A | 0.5263 | 0.4582 | 0.1912 | 0.078* | |
H3B | 0.4735 | 0.3572 | 0.2258 | 0.078* | |
C4 | 0.2216 (7) | 0.1737 (6) | 0.0867 (6) | 0.0548 (18) | |
C5 | 0.1431 (8) | 0.0209 (6) | 0.1158 (7) | 0.064 (2) | |
C6 | 0.1256 (7) | 0.0941 (6) | 0.1728 (6) | 0.058 (2) | |
C7 | 0.0668 (9) | 0.0654 (7) | 0.2332 (7) | 0.071 (2) | |
H7 | 0.0530 | 0.1132 | 0.2699 | 0.085* | |
C8 | 0.0284 (10) | −0.0386 (8) | 0.2375 (8) | 0.086 (3) | |
H8 | −0.0109 | −0.0611 | 0.2787 | 0.104* | |
C9 | 0.0480 (12) | −0.1097 (8) | 0.1807 (10) | 0.098 (4) | |
H9 | 0.0194 | −0.1792 | 0.1846 | 0.118* | |
C10 | 0.1049 (10) | −0.0841 (7) | 0.1219 (10) | 0.090 (3) | |
H10 | 0.1190 | −0.1324 | 0.0864 | 0.108* | |
C11 | 0.2406 (11) | 0.0263 (8) | −0.0060 (8) | 0.088 (3) | |
H11A | 0.3264 | 0.0361 | 0.0365 | 0.133* | |
H11B | 0.2432 | 0.0621 | −0.0570 | 0.133* | |
H11C | 0.1772 | −0.0500 | −0.0425 | 0.133* | |
C12 | 0.1750 (8) | 0.4097 (6) | 0.0041 (6) | 0.0538 (18) | |
C13 | −0.0117 (11) | 0.3958 (7) | −0.1021 (7) | 0.074 (3) | |
C14 | −0.0247 (8) | 0.3530 (6) | −0.0231 (6) | 0.060 (2) | |
C15 | −0.1424 (9) | 0.3112 (7) | −0.0193 (7) | 0.070 (2) | |
H15 | −0.1516 | 0.2839 | 0.0333 | 0.084* | |
C16 | −0.2467 (11) | 0.3130 (9) | −0.1009 (9) | 0.095 (3) | |
H16 | −0.3276 | 0.2856 | −0.1021 | 0.114* | |
C17 | −0.2336 (13) | 0.3533 (10) | −0.1780 (9) | 0.095 (3) | |
H17 | −0.3059 | 0.3514 | −0.2308 | 0.114* | |
C18 | −0.1203 (13) | 0.3951 (9) | −0.1793 (8) | 0.092 (3) | |
H18 | −0.1129 | 0.4240 | −0.2314 | 0.111* | |
C19 | 0.1741 (12) | 0.4828 (9) | −0.1429 (8) | 0.094 (3) | |
H19A | 0.1449 | 0.5325 | −0.1621 | 0.141* | |
H19B | 0.1480 | 0.4287 | −0.2060 | 0.141* | |
H19C | 0.2686 | 0.5219 | −0.1000 | 0.141* | |
C20 | 0.4631 (8) | 0.4824 (6) | 0.2959 (6) | 0.0554 (18) | |
C21 | 0.5376 (9) | 0.6073 (7) | 0.4445 (6) | 0.062 (2) | |
C22 | 0.4016 (8) | 0.5502 (6) | 0.3924 (6) | 0.0543 (18) | |
C23 | 0.3320 (9) | 0.5747 (7) | 0.4340 (6) | 0.062 (2) | |
H23 | 0.2402 | 0.5367 | 0.3995 | 0.075* | |
C24 | 0.4090 (12) | 0.6613 (8) | 0.5328 (8) | 0.083 (3) | |
H24 | 0.3660 | 0.6807 | 0.5637 | 0.100* | |
C25 | 0.5447 (12) | 0.7178 (9) | 0.5846 (8) | 0.092 (3) | |
H25 | 0.5917 | 0.7746 | 0.6490 | 0.110* | |
C26 | 0.6109 (11) | 0.6908 (8) | 0.5418 (7) | 0.085 (3) | |
H26 | 0.7027 | 0.7275 | 0.5770 | 0.102* | |
C27 | 0.7098 (9) | 0.5979 (9) | 0.4038 (9) | 0.091 (3) | |
H27A | 0.7384 | 0.6556 | 0.3769 | 0.136* | |
H27B | 0.7132 | 0.5381 | 0.3700 | 0.136* | |
H27C | 0.7667 | 0.6236 | 0.4791 | 0.136* | |
C28 | 0.564 (4) | 0.158 (3) | 0.226 (2) | 0.198 (9) | 0.50 |
H28 | 0.5561 | 0.1270 | 0.2766 | 0.238* | 0.50 |
C29 | 0.630 (4) | 0.044 (3) | 0.183 (3) | 0.207 (10) | 0.50 |
H29A | 0.7233 | 0.0704 | 0.2147 | 0.310* | 0.50 |
H29B | 0.5847 | −0.0151 | 0.1169 | 0.310* | 0.50 |
H29C | 0.5988 | 0.0180 | 0.2299 | 0.310* | 0.50 |
C30 | 0.607 (4) | 0.150 (3) | 0.066 (3) | 0.205 (10) | 0.50 |
H30A | 0.6091 | 0.2173 | 0.0640 | 0.308* | 0.50 |
H30B | 0.5290 | 0.0913 | 0.0042 | 0.308* | 0.50 |
H30C | 0.6838 | 0.1537 | 0.0659 | 0.308* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0486 (5) | 0.0468 (5) | 0.0512 (5) | 0.0267 (4) | 0.0244 (4) | 0.0156 (4) |
I1 | 0.0762 (5) | 0.0963 (5) | 0.0871 (5) | 0.0451 (4) | 0.0503 (4) | 0.0340 (4) |
Cl1 | 0.0785 (15) | 0.0850 (16) | 0.1106 (19) | 0.0383 (13) | 0.0627 (15) | 0.0453 (14) |
N1 | 0.040 (3) | 0.032 (3) | 0.040 (3) | 0.015 (2) | 0.013 (2) | 0.008 (2) |
N2 | 0.051 (3) | 0.049 (3) | 0.056 (4) | 0.030 (3) | 0.024 (3) | 0.017 (3) |
N3 | 0.059 (4) | 0.052 (4) | 0.075 (5) | 0.032 (3) | 0.026 (4) | 0.004 (3) |
N4 | 0.059 (4) | 0.050 (4) | 0.053 (4) | 0.032 (3) | 0.023 (3) | 0.016 (3) |
N5 | 0.086 (5) | 0.058 (4) | 0.064 (4) | 0.044 (4) | 0.039 (4) | 0.028 (3) |
N6 | 0.052 (4) | 0.048 (3) | 0.052 (4) | 0.028 (3) | 0.022 (3) | 0.019 (3) |
N7 | 0.050 (4) | 0.064 (4) | 0.056 (4) | 0.025 (3) | 0.015 (3) | 0.024 (3) |
N8 | 0.165 (12) | 0.217 (15) | 0.128 (11) | 0.135 (11) | 0.018 (10) | −0.026 (12) |
O1 | 0.104 (4) | 0.131 (5) | 0.117 (5) | 0.051 (4) | 0.076 (4) | 0.048 (4) |
O2 | 0.103 (7) | 0.116 (7) | 0.136 (8) | 0.037 (7) | 0.047 (7) | 0.046 (7) |
O3 | 0.104 (7) | 0.127 (8) | 0.122 (7) | 0.042 (7) | 0.058 (6) | 0.065 (7) |
O4 | 0.107 (7) | 0.109 (7) | 0.124 (7) | 0.054 (6) | 0.065 (6) | 0.039 (6) |
O2' | 0.120 (7) | 0.107 (6) | 0.134 (7) | 0.049 (6) | 0.050 (6) | 0.061 (6) |
O3' | 0.110 (6) | 0.113 (7) | 0.124 (7) | 0.025 (6) | 0.059 (6) | 0.044 (6) |
O4' | 0.101 (7) | 0.121 (7) | 0.125 (7) | 0.059 (6) | 0.056 (6) | 0.041 (6) |
O5 | 0.162 (11) | 0.178 (13) | 0.104 (9) | 0.143 (10) | 0.014 (9) | −0.002 (9) |
C1 | 0.073 (5) | 0.063 (5) | 0.072 (5) | 0.041 (5) | 0.043 (5) | 0.020 (4) |
C2 | 0.073 (5) | 0.053 (4) | 0.069 (5) | 0.032 (4) | 0.043 (5) | 0.026 (4) |
C3 | 0.054 (5) | 0.068 (5) | 0.079 (6) | 0.032 (4) | 0.038 (4) | 0.026 (4) |
C4 | 0.049 (4) | 0.052 (4) | 0.063 (5) | 0.029 (4) | 0.025 (4) | 0.016 (4) |
C5 | 0.049 (4) | 0.044 (4) | 0.072 (5) | 0.019 (4) | 0.014 (4) | 0.005 (4) |
C6 | 0.046 (4) | 0.044 (4) | 0.058 (5) | 0.018 (4) | 0.009 (4) | 0.013 (4) |
C7 | 0.074 (6) | 0.055 (5) | 0.064 (5) | 0.024 (4) | 0.027 (5) | 0.017 (4) |
C8 | 0.075 (6) | 0.060 (6) | 0.087 (7) | 0.015 (5) | 0.025 (5) | 0.030 (5) |
C9 | 0.107 (9) | 0.045 (5) | 0.113 (9) | 0.027 (6) | 0.039 (7) | 0.031 (6) |
C10 | 0.081 (7) | 0.050 (6) | 0.119 (9) | 0.034 (5) | 0.033 (7) | 0.024 (6) |
C11 | 0.092 (7) | 0.077 (6) | 0.091 (7) | 0.050 (6) | 0.040 (6) | 0.002 (5) |
C12 | 0.072 (5) | 0.042 (4) | 0.052 (4) | 0.032 (4) | 0.031 (4) | 0.016 (3) |
C13 | 0.105 (8) | 0.055 (5) | 0.058 (5) | 0.052 (5) | 0.025 (5) | 0.019 (4) |
C14 | 0.069 (5) | 0.045 (4) | 0.058 (5) | 0.036 (4) | 0.019 (4) | 0.008 (4) |
C15 | 0.066 (5) | 0.066 (5) | 0.080 (6) | 0.043 (5) | 0.028 (5) | 0.019 (4) |
C16 | 0.082 (7) | 0.083 (7) | 0.102 (8) | 0.056 (6) | 0.018 (6) | 0.016 (6) |
C17 | 0.100 (8) | 0.110 (9) | 0.093 (8) | 0.080 (8) | 0.031 (7) | 0.045 (7) |
C18 | 0.121 (9) | 0.096 (8) | 0.070 (6) | 0.081 (8) | 0.027 (6) | 0.027 (5) |
C19 | 0.122 (9) | 0.102 (8) | 0.085 (7) | 0.066 (7) | 0.056 (7) | 0.059 (6) |
C20 | 0.052 (4) | 0.053 (4) | 0.066 (5) | 0.031 (4) | 0.027 (4) | 0.028 (4) |
C21 | 0.070 (6) | 0.060 (5) | 0.049 (5) | 0.034 (5) | 0.020 (4) | 0.025 (4) |
C22 | 0.065 (5) | 0.053 (4) | 0.046 (4) | 0.035 (4) | 0.021 (4) | 0.023 (3) |
C23 | 0.069 (5) | 0.065 (5) | 0.048 (4) | 0.038 (4) | 0.022 (4) | 0.016 (4) |
C24 | 0.117 (9) | 0.082 (7) | 0.064 (6) | 0.058 (7) | 0.046 (6) | 0.030 (5) |
C25 | 0.100 (8) | 0.090 (7) | 0.050 (5) | 0.045 (7) | 0.013 (6) | 0.010 (5) |
C26 | 0.076 (6) | 0.082 (7) | 0.056 (6) | 0.031 (6) | 0.006 (5) | 0.023 (5) |
C27 | 0.056 (5) | 0.104 (8) | 0.093 (7) | 0.036 (5) | 0.022 (5) | 0.041 (6) |
C28 | 0.176 (12) | 0.224 (15) | 0.124 (11) | 0.121 (12) | 0.018 (11) | −0.030 (12) |
C29 | 0.186 (13) | 0.214 (16) | 0.143 (13) | 0.125 (13) | 0.012 (12) | −0.012 (13) |
C30 | 0.180 (13) | 0.219 (16) | 0.133 (12) | 0.108 (13) | 0.014 (13) | −0.002 (13) |
Zn1—N4 | 2.064 (6) | C6—C7 | 1.362 (12) |
Zn1—N6 | 2.069 (6) | C7—C8 | 1.388 (12) |
Zn1—N2 | 2.080 (6) | C7—H7 | 0.9300 |
Zn1—N1 | 2.442 (5) | C8—C9 | 1.393 (16) |
Zn1—I1 | 2.6148 (10) | C8—H8 | 0.9300 |
Cl1—O2 | 1.387 (11) | C9—C10 | 1.318 (16) |
Cl1—O2' | 1.394 (10) | C9—H9 | 0.9300 |
Cl1—O1 | 1.406 (6) | C10—H10 | 0.9300 |
Cl1—O4' | 1.423 (10) | C11—H11A | 0.9600 |
Cl1—O4 | 1.426 (12) | C11—H11B | 0.9600 |
Cl1—O3 | 1.442 (12) | C11—H11C | 0.9600 |
Cl1—O3' | 1.495 (11) | C13—C18 | 1.400 (14) |
N1—C2 | 1.440 (9) | C13—C14 | 1.407 (12) |
N1—C1 | 1.445 (9) | C14—C15 | 1.393 (12) |
N1—C3 | 1.448 (9) | C15—C16 | 1.412 (13) |
N2—C4 | 1.322 (9) | C15—H15 | 0.9300 |
N2—C6 | 1.414 (9) | C16—C17 | 1.364 (16) |
N3—C4 | 1.347 (9) | C16—H16 | 0.9300 |
N3—C5 | 1.377 (11) | C17—C18 | 1.323 (16) |
N3—C11 | 1.455 (11) | C17—H17 | 0.9300 |
N4—C12 | 1.308 (10) | C18—H18 | 0.9300 |
N4—C14 | 1.403 (10) | C19—H19A | 0.9600 |
N5—C12 | 1.350 (10) | C19—H19B | 0.9600 |
N5—C13 | 1.374 (12) | C19—H19C | 0.9600 |
N5—C19 | 1.450 (11) | C21—C22 | 1.377 (11) |
N6—C20 | 1.306 (10) | C21—C26 | 1.387 (13) |
N6—C22 | 1.405 (9) | C22—C23 | 1.377 (11) |
N7—C20 | 1.343 (10) | C23—C24 | 1.417 (12) |
N7—C21 | 1.392 (11) | C23—H23 | 0.9300 |
N7—C27 | 1.450 (11) | C24—C25 | 1.374 (15) |
N8—C28 | 1.298 (19) | C24—H24 | 0.9300 |
N8—C29 | 1.473 (19) | C25—C26 | 1.365 (15) |
N8—C30 | 1.474 (19) | C25—H25 | 0.9300 |
O5—C28 | 1.197 (19) | C26—H26 | 0.9300 |
C1—C4 | 1.501 (11) | C27—H27A | 0.9600 |
C1—H1A | 0.9700 | C27—H27B | 0.9600 |
C1—H1B | 0.9700 | C27—H27C | 0.9600 |
C2—C12 | 1.468 (11) | C28—H28 | 0.9300 |
C2—H2A | 0.9700 | C29—H29A | 0.9600 |
C2—H2B | 0.9700 | C29—H29B | 0.9600 |
C3—C20 | 1.490 (11) | C29—H29C | 0.9600 |
C3—H3A | 0.9700 | C30—H30A | 0.9600 |
C3—H3B | 0.9700 | C30—H30B | 0.9600 |
C5—C6 | 1.398 (11) | C30—H30C | 0.9600 |
C5—C10 | 1.411 (12) | ||
N4—Zn1—N6 | 112.9 (2) | C6—C7—H7 | 121.6 |
N4—Zn1—N2 | 110.7 (2) | C8—C7—H7 | 121.6 |
N6—Zn1—N2 | 115.2 (2) | C7—C8—C9 | 120.8 (10) |
N4—Zn1—N1 | 73.9 (2) | C7—C8—H8 | 119.6 |
N6—Zn1—N1 | 74.2 (2) | C9—C8—H8 | 119.6 |
N2—Zn1—N1 | 74.6 (2) | C10—C9—C8 | 123.7 (9) |
N4—Zn1—I1 | 106.57 (19) | C10—C9—H9 | 118.2 |
N6—Zn1—I1 | 105.53 (17) | C8—C9—H9 | 118.2 |
N2—Zn1—I1 | 105.19 (17) | C9—C10—C5 | 116.2 (10) |
N1—Zn1—I1 | 179.50 (13) | C9—C10—H10 | 121.9 |
O2—Cl1—O2' | 34.7 (9) | C5—C10—H10 | 121.9 |
O2—Cl1—O1 | 112.7 (9) | N3—C11—H11A | 109.5 |
O2'—Cl1—O1 | 112.6 (8) | N3—C11—H11B | 109.5 |
O2—Cl1—O4' | 81.0 (10) | H11A—C11—H11B | 109.5 |
O2'—Cl1—O4' | 110.6 (9) | N3—C11—H11C | 109.5 |
O1—Cl1—O4' | 115.5 (7) | H11A—C11—H11C | 109.5 |
O2—Cl1—O4 | 113.4 (10) | H11B—C11—H11C | 109.5 |
O2'—Cl1—O4 | 138.0 (10) | N4—C12—N5 | 113.1 (7) |
O1—Cl1—O4 | 105.5 (8) | N4—C12—C2 | 121.8 (7) |
O4'—Cl1—O4 | 32.9 (8) | N5—C12—C2 | 125.1 (7) |
O2—Cl1—O3 | 108.3 (10) | N5—C13—C18 | 134.0 (10) |
O2'—Cl1—O3 | 76.0 (10) | N5—C13—C14 | 107.0 (7) |
O1—Cl1—O3 | 108.1 (9) | C18—C13—C14 | 119.0 (11) |
O4'—Cl1—O3 | 127.4 (11) | C15—C14—N4 | 131.5 (8) |
O4—Cl1—O3 | 108.6 (10) | C15—C14—C13 | 121.6 (8) |
O2—Cl1—O3' | 130.3 (10) | N4—C14—C13 | 106.9 (8) |
O2'—Cl1—O3' | 104.4 (8) | C14—C15—C16 | 115.4 (10) |
O1—Cl1—O3' | 109.7 (7) | C14—C15—H15 | 122.3 |
O4'—Cl1—O3' | 103.1 (9) | C16—C15—H15 | 122.3 |
O4—Cl1—O3' | 77.8 (10) | C17—C16—C15 | 122.6 (11) |
O3—Cl1—O3' | 31.9 (10) | C17—C16—H16 | 118.7 |
C2—N1—C1 | 114.2 (6) | C15—C16—H16 | 118.7 |
C2—N1—C3 | 114.5 (6) | C18—C17—C16 | 121.4 (10) |
C1—N1—C3 | 113.6 (6) | C18—C17—H17 | 119.3 |
C2—N1—Zn1 | 103.2 (4) | C16—C17—H17 | 119.3 |
C1—N1—Zn1 | 105.8 (4) | C17—C18—C13 | 120.0 (11) |
C3—N1—Zn1 | 103.9 (4) | C17—C18—H18 | 120.0 |
C4—N2—C6 | 106.1 (6) | C13—C18—H18 | 120.0 |
C4—N2—Zn1 | 117.3 (5) | N5—C19—H19A | 109.5 |
C6—N2—Zn1 | 136.1 (5) | N5—C19—H19B | 109.5 |
C4—N3—C5 | 106.7 (7) | H19A—C19—H19B | 109.5 |
C4—N3—C11 | 127.5 (8) | N5—C19—H19C | 109.5 |
C5—N3—C11 | 125.8 (7) | H19A—C19—H19C | 109.5 |
C12—N4—C14 | 106.4 (7) | H19B—C19—H19C | 109.5 |
C12—N4—Zn1 | 118.0 (5) | N6—C20—N7 | 113.4 (7) |
C14—N4—Zn1 | 135.4 (6) | N6—C20—C3 | 122.3 (7) |
C12—N5—C13 | 106.6 (7) | N7—C20—C3 | 124.3 (7) |
C12—N5—C19 | 126.8 (8) | C22—C21—C26 | 121.8 (9) |
C13—N5—C19 | 126.5 (8) | C22—C21—N7 | 106.5 (7) |
C20—N6—C22 | 105.5 (6) | C26—C21—N7 | 131.7 (9) |
C20—N6—Zn1 | 117.7 (5) | C21—C22—C23 | 121.3 (7) |
C22—N6—Zn1 | 136.2 (5) | C21—C22—N6 | 108.3 (7) |
C20—N7—C21 | 106.3 (7) | C23—C22—N6 | 130.4 (7) |
C20—N7—C27 | 127.6 (8) | C22—C23—C24 | 115.9 (9) |
C21—N7—C27 | 126.1 (8) | C22—C23—H23 | 122.0 |
C28—N8—C29 | 108 (3) | C24—C23—H23 | 122.0 |
C28—N8—C30 | 138 (3) | C25—C24—C23 | 122.5 (10) |
C29—N8—C30 | 113 (3) | C25—C24—H24 | 118.7 |
N1—C1—C4 | 110.0 (6) | C23—C24—H24 | 118.7 |
N1—C1—H1A | 109.7 | C26—C25—C24 | 120.2 (10) |
C4—C1—H1A | 109.7 | C26—C25—H25 | 119.9 |
N1—C1—H1B | 109.7 | C24—C25—H25 | 119.9 |
C4—C1—H1B | 109.7 | C25—C26—C21 | 118.3 (10) |
H1A—C1—H1B | 108.2 | C25—C26—H26 | 120.8 |
N1—C2—C12 | 110.2 (6) | C21—C26—H26 | 120.8 |
N1—C2—H2A | 109.6 | N7—C27—H27A | 109.5 |
C12—C2—H2A | 109.6 | N7—C27—H27B | 109.5 |
N1—C2—H2B | 109.6 | H27A—C27—H27B | 109.5 |
C12—C2—H2B | 109.6 | N7—C27—H27C | 109.5 |
H2A—C2—H2B | 108.1 | H27A—C27—H27C | 109.5 |
N1—C3—C20 | 110.3 (6) | H27B—C27—H27C | 109.5 |
N1—C3—H3A | 109.6 | O5—C28—N8 | 109 (3) |
C20—C3—H3A | 109.6 | O5—C28—H28 | 125.4 |
N1—C3—H3B | 109.6 | N8—C28—H28 | 125.4 |
C20—C3—H3B | 109.6 | N8—C29—H29A | 109.5 |
H3A—C3—H3B | 108.1 | N8—C29—H29B | 109.5 |
N2—C4—N3 | 112.8 (7) | H29A—C29—H29B | 109.5 |
N2—C4—C1 | 123.0 (7) | N8—C29—H29C | 109.5 |
N3—C4—C1 | 124.2 (7) | H29A—C29—H29C | 109.5 |
N3—C5—C6 | 107.7 (7) | H29B—C29—H29C | 109.5 |
N3—C5—C10 | 131.2 (9) | N8—C30—H30A | 109.5 |
C6—C5—C10 | 121.1 (10) | N8—C30—H30B | 109.5 |
C7—C6—C5 | 121.3 (8) | H30A—C30—H30B | 109.5 |
C7—C6—N2 | 131.9 (8) | N8—C30—H30C | 109.5 |
C5—C6—N2 | 106.7 (7) | H30A—C30—H30C | 109.5 |
C6—C7—C8 | 116.8 (9) | H30B—C30—H30C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [ZnI(C27H27N7)]ClO4·0.5C3H7NO |
Mr | 777.82 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 12.743 (2), 14.399 (3), 14.554 (3) |
α, β, γ (°) | 97.562 (2), 112.766 (2), 114.420 (2) |
V (Å3) | 2102.7 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.42 |
Crystal size (mm) | 0.50 × 0.42 × 0.39 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.537, 0.608 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10873, 7231, 4303 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.245, 1.09 |
No. of reflections | 7231 |
No. of parameters | 443 |
No. of restraints | 251 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.18, −0.56 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Sheldrick, 1996), SHELXTL.
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The asymmetric unit of the title compound, (Fig. 1), consists of a [Zn(Mentb)(I)] cation, a perchlorate anion and half a DMF molecule. The perchlorate anions is disordered and the DMF solvent is half occupancy. The ZnII ion is five-coordinate with a N4I ligand set. The Mentb ligand acts as a tetradentate N-donor, and an iodide completes the coordination. The coordination geometry of the ZnII may be best described as trigonal-bipyramidal, with approximate C3 molecular site symmetry. This geometry is assumed by the ZnII to relieve the steric crowding. The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the ZnII atom protrudes towards I and is 0.563 (5) Å from the plane of atoms N2/N4/N6. The axial sites are occupyied by N1 and I1, with Zn1—N1 2.442 (5) Å, Zn1—I1 2.6148 (10) Å and N1—Zn1—I1 is 179.50 (13)°. The three benzimidazole ring arms of the Mentb ligand form a cone-shaped cavity. The angles N2—Zn1—N6, N2—Zn1—N4 and N4—Zn1—N6 are 115.2 (2), 110.7 (2) and 112.9 (2) °, respectively. The N1—Zn1—N2 74.6 (2), N1—Zn1—N4 73.9 (2) and N1—Zn1—N6, 74.2 (2)° angles, which are all ca 16 ° less than the ideal value of 90°, are imposed by the geometry of the Mentb ligand. The bond angles and distance in the three benzimidazole groups are equal within experimental error. In the crystal structure, there are weak π···π stacking interactions with a centroid···centroid distance of 3.542 (6)Å bewteen inversion related molecules (see Fig. 2). Some references related to the title compound are Pandey et al. (1992), Addison et al. (1981) & Wu et al., (2006).