The title compound, [Zn(C
16H
13BrN
3)Cl]·CH
4O, has been prepared by the reaction of 2-[2-(1
H-benzimidazol-2-yl)ethyliminomethyl]-4-bromophenol with zinc(II) chloride. The central Zn atom is coordinated by two N atoms and one O atom from the phenolate ligand, along with a Cl
− anion, which provide a distorted tetrahedral enviroment. Intermolecular O—H
O and N—H
O hydrogen bonds link two Zn complex molecules and two methanol solvent molecules into a centrosymmetric cluster. The crystal packing is further stabilized by weak C—H
Cl hydrogen bonds.
Supporting information
CCDC reference: 289702
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.096
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B .. CL1 .. 2.88 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C16 H13 Br Cl N3 O Zn
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C H4 O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
0 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1998); software used to prepare material for publication: SHELXTL-NT.
{2-[2-(1
H-Benzimidazol-2-yl)ethyliminomethyl]-4-bromophenolato}chlorozinc(II) methanol solvate
top
Crystal data top
[Zn(C16H13BrN3O)Cl]·CH4O | F(000) = 952 |
Mr = 476.07 | Dx = 1.666 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4425 (17) Å | Cell parameters from 2554 reflections |
b = 13.989 (3) Å | θ = 2.3–23.5° |
c = 18.936 (4) Å | µ = 3.56 mm−1 |
β = 105.739 (8)° | T = 294 K |
V = 1897.6 (7) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.20 × 0.12 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3864 independent reflections |
Radiation source: fine-focus sealed tube | 2350 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→7 |
Tmin = 0.495, Tmax = 0.653 | k = −17→9 |
10548 measured reflections | l = −22→23 |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0356P)2 + 0.893P] where P = (Fo2 + 2Fc2)/3 |
3864 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.19174 (11) | 0.00495 (4) | −0.04631 (3) | 0.0980 (3) | |
Zn1 | 0.65924 (7) | −0.14022 (3) | −0.32350 (2) | 0.03826 (15) | |
Cl1 | 0.79331 (17) | −0.28086 (7) | −0.29861 (6) | 0.0562 (3) | |
O1 | 0.4122 (4) | −0.14780 (19) | −0.30825 (14) | 0.0490 (7) | |
N1 | 0.7185 (5) | −0.0165 (2) | −0.26723 (16) | 0.0401 (8) | |
N2 | 0.6965 (5) | −0.0841 (2) | −0.41573 (16) | 0.0395 (8) | |
N3 | 0.7772 (5) | 0.0184 (2) | −0.48977 (17) | 0.0442 (9) | |
H3A | 0.8141 | 0.0708 | −0.5051 | 0.053* | |
C1 | 0.3749 (6) | −0.1133 (3) | −0.2487 (2) | 0.0408 (10) | |
C2 | 0.4723 (6) | −0.0370 (3) | −0.2065 (2) | 0.0418 (10) | |
C3 | 0.4145 (7) | −0.0026 (3) | −0.1467 (2) | 0.0523 (12) | |
H3 | 0.4763 | 0.0492 | −0.1201 | 0.063* | |
C4 | 0.2691 (8) | −0.0437 (3) | −0.1269 (2) | 0.0580 (13) | |
C5 | 0.1734 (7) | −0.1191 (3) | −0.1669 (3) | 0.0587 (13) | |
H5 | 0.0743 | −0.1471 | −0.1534 | 0.070* | |
C6 | 0.2243 (6) | −0.1531 (3) | −0.2270 (2) | 0.0497 (11) | |
H6 | 0.1577 | −0.2035 | −0.2539 | 0.060* | |
C7 | 0.6260 (6) | 0.0138 (3) | −0.2241 (2) | 0.0453 (11) | |
H7 | 0.6590 | 0.0730 | −0.2022 | 0.054* | |
C8 | 0.8580 (6) | 0.0464 (3) | −0.2858 (2) | 0.0466 (11) | |
H8A | 0.9746 | 0.0119 | −0.2789 | 0.056* | |
H8B | 0.8809 | 0.1012 | −0.2532 | 0.056* | |
C9 | 0.7890 (6) | 0.0802 (3) | −0.3653 (2) | 0.0426 (10) | |
H9A | 0.6737 | 0.1154 | −0.3708 | 0.051* | |
H9B | 0.8802 | 0.1245 | −0.3747 | 0.051* | |
C10 | 0.7548 (6) | 0.0039 (3) | −0.4226 (2) | 0.0385 (9) | |
C11 | 0.6808 (5) | −0.1297 (3) | −0.4826 (2) | 0.0383 (9) | |
C12 | 0.7313 (6) | −0.0648 (3) | −0.5301 (2) | 0.0418 (10) | |
C13 | 0.7299 (6) | −0.0903 (4) | −0.6007 (2) | 0.0569 (12) | |
H13 | 0.7622 | −0.0468 | −0.6324 | 0.068* | |
C14 | 0.6795 (7) | −0.1816 (4) | −0.6223 (2) | 0.0611 (13) | |
H14 | 0.6775 | −0.2004 | −0.6696 | 0.073* | |
C15 | 0.6306 (7) | −0.2477 (3) | −0.5753 (2) | 0.0587 (13) | |
H15 | 0.5984 | −0.3096 | −0.5918 | 0.070* | |
C16 | 0.6293 (6) | −0.2226 (3) | −0.5049 (2) | 0.0486 (11) | |
H16 | 0.5954 | −0.2662 | −0.4738 | 0.058* | |
O2 | 0.1575 (5) | −0.1743 (2) | −0.43534 (16) | 0.0736 (10) | |
H2 | 0.2300 | −0.1693 | −0.3943 | 0.088* | |
C17 | 0.1250 (9) | −0.2700 (4) | −0.4523 (3) | 0.0934 (19) | |
H17A | 0.2409 | −0.3044 | −0.4382 | 0.140* | |
H17B | 0.0704 | −0.2769 | −0.5041 | 0.140* | |
H17C | 0.0413 | −0.2952 | −0.4263 | 0.140* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.1586 (7) | 0.0746 (4) | 0.0929 (5) | 0.0212 (4) | 0.0890 (5) | 0.0027 (3) |
Zn1 | 0.0496 (3) | 0.0298 (2) | 0.0366 (2) | −0.0035 (2) | 0.0138 (2) | −0.0009 (2) |
Cl1 | 0.0691 (8) | 0.0341 (6) | 0.0662 (7) | 0.0054 (5) | 0.0197 (6) | 0.0079 (5) |
O1 | 0.0514 (19) | 0.0530 (17) | 0.0440 (16) | −0.0090 (14) | 0.0153 (14) | −0.0140 (13) |
N1 | 0.048 (2) | 0.0363 (19) | 0.0329 (18) | −0.0062 (15) | 0.0058 (16) | −0.0022 (14) |
N2 | 0.053 (2) | 0.0297 (18) | 0.0377 (18) | 0.0007 (15) | 0.0160 (16) | 0.0037 (14) |
N3 | 0.047 (2) | 0.043 (2) | 0.045 (2) | 0.0014 (16) | 0.0167 (17) | 0.0134 (16) |
C1 | 0.043 (3) | 0.038 (2) | 0.041 (2) | 0.0075 (18) | 0.0101 (19) | 0.0068 (18) |
C2 | 0.059 (3) | 0.029 (2) | 0.040 (2) | 0.0039 (19) | 0.019 (2) | 0.0057 (18) |
C3 | 0.081 (4) | 0.036 (2) | 0.045 (2) | 0.015 (2) | 0.024 (2) | 0.0026 (19) |
C4 | 0.083 (4) | 0.046 (3) | 0.057 (3) | 0.022 (3) | 0.040 (3) | 0.014 (2) |
C5 | 0.057 (3) | 0.060 (3) | 0.066 (3) | 0.015 (2) | 0.028 (3) | 0.019 (2) |
C6 | 0.048 (3) | 0.049 (3) | 0.054 (3) | 0.005 (2) | 0.018 (2) | 0.005 (2) |
C7 | 0.067 (3) | 0.030 (2) | 0.036 (2) | −0.001 (2) | 0.009 (2) | −0.0040 (17) |
C8 | 0.048 (3) | 0.041 (2) | 0.049 (2) | −0.013 (2) | 0.010 (2) | −0.0055 (19) |
C9 | 0.046 (3) | 0.031 (2) | 0.054 (3) | −0.0029 (18) | 0.018 (2) | 0.0034 (19) |
C10 | 0.037 (2) | 0.036 (2) | 0.041 (2) | 0.0070 (18) | 0.0096 (19) | 0.0096 (18) |
C11 | 0.039 (2) | 0.040 (2) | 0.036 (2) | 0.0021 (18) | 0.0103 (18) | −0.0018 (18) |
C12 | 0.042 (3) | 0.043 (2) | 0.041 (2) | 0.0051 (19) | 0.0124 (19) | 0.0076 (19) |
C13 | 0.053 (3) | 0.077 (4) | 0.043 (3) | 0.005 (3) | 0.018 (2) | 0.012 (2) |
C14 | 0.068 (4) | 0.075 (3) | 0.039 (3) | 0.009 (3) | 0.012 (2) | −0.008 (2) |
C15 | 0.069 (4) | 0.056 (3) | 0.049 (3) | 0.001 (2) | 0.013 (2) | −0.015 (2) |
C16 | 0.060 (3) | 0.045 (3) | 0.042 (2) | 0.000 (2) | 0.016 (2) | −0.0023 (19) |
O2 | 0.095 (3) | 0.058 (2) | 0.0528 (18) | −0.0312 (18) | −0.0058 (18) | 0.0126 (16) |
C17 | 0.095 (5) | 0.064 (4) | 0.102 (4) | −0.010 (3) | −0.005 (4) | −0.004 (3) |
Geometric parameters (Å, º) top
Br1—C4 | 1.897 (4) | C7—H7 | 0.9300 |
Zn1—O1 | 1.940 (3) | C8—C9 | 1.528 (5) |
Zn1—N2 | 2.002 (3) | C8—H8A | 0.9700 |
Zn1—N1 | 2.018 (3) | C8—H8B | 0.9700 |
Zn1—Cl1 | 2.1985 (12) | C9—C10 | 1.495 (5) |
O1—C1 | 1.323 (4) | C9—H9A | 0.9700 |
N1—C7 | 1.274 (5) | C9—H9B | 0.9700 |
N1—C8 | 1.473 (5) | C11—C16 | 1.389 (5) |
N2—C10 | 1.323 (4) | C11—C12 | 1.400 (5) |
N2—C11 | 1.394 (4) | C12—C13 | 1.381 (5) |
N3—C10 | 1.342 (5) | C13—C14 | 1.362 (6) |
N3—C12 | 1.384 (5) | C13—H13 | 0.9300 |
N3—H3A | 0.8600 | C14—C15 | 1.398 (6) |
C1—C6 | 1.409 (6) | C14—H14 | 0.9300 |
C1—C2 | 1.411 (5) | C15—C16 | 1.381 (5) |
C2—C3 | 1.400 (5) | C15—H15 | 0.9300 |
C2—C7 | 1.460 (6) | C16—H16 | 0.9300 |
C3—C4 | 1.365 (6) | O2—C17 | 1.382 (5) |
C3—H3 | 0.9300 | O2—H2 | 0.8200 |
C4—C5 | 1.379 (6) | C17—H17A | 0.9600 |
C5—C6 | 1.377 (6) | C17—H17B | 0.9600 |
C5—H5 | 0.9300 | C17—H17C | 0.9600 |
C6—H6 | 0.9300 | | |
| | | |
O1—Zn1—N2 | 120.83 (12) | C9—C8—H8A | 109.6 |
O1—Zn1—N1 | 92.78 (12) | N1—C8—H8B | 109.6 |
N2—Zn1—N1 | 93.55 (12) | C9—C8—H8B | 109.6 |
O1—Zn1—Cl1 | 108.21 (9) | H8A—C8—H8B | 108.1 |
N2—Zn1—Cl1 | 112.08 (9) | C10—C9—C8 | 116.1 (3) |
N1—Zn1—Cl1 | 129.27 (10) | C10—C9—H9A | 108.3 |
C1—O1—Zn1 | 122.2 (3) | C8—C9—H9A | 108.3 |
C7—N1—C8 | 119.5 (3) | C10—C9—H9B | 108.3 |
C7—N1—Zn1 | 123.0 (3) | C8—C9—H9B | 108.3 |
C8—N1—Zn1 | 116.9 (3) | H9A—C9—H9B | 107.4 |
C10—N2—C11 | 106.6 (3) | N2—C10—N3 | 111.3 (3) |
C10—N2—Zn1 | 125.3 (3) | N2—C10—C9 | 126.1 (3) |
C11—N2—Zn1 | 128.0 (2) | N3—C10—C9 | 122.6 (3) |
C10—N3—C12 | 108.7 (3) | C16—C11—N2 | 130.8 (3) |
C10—N3—H3A | 125.7 | C16—C11—C12 | 120.8 (3) |
C12—N3—H3A | 125.7 | N2—C11—C12 | 108.4 (3) |
O1—C1—C6 | 118.1 (4) | C13—C12—N3 | 133.5 (4) |
O1—C1—C2 | 124.4 (4) | C13—C12—C11 | 121.5 (4) |
C6—C1—C2 | 117.4 (4) | N3—C12—C11 | 105.1 (3) |
C3—C2—C1 | 119.6 (4) | C14—C13—C12 | 117.5 (4) |
C3—C2—C7 | 116.7 (4) | C14—C13—H13 | 121.3 |
C1—C2—C7 | 123.5 (4) | C12—C13—H13 | 121.3 |
C4—C3—C2 | 121.2 (4) | C13—C14—C15 | 121.9 (4) |
C4—C3—H3 | 119.4 | C13—C14—H14 | 119.1 |
C2—C3—H3 | 119.4 | C15—C14—H14 | 119.1 |
C3—C4—C5 | 120.0 (4) | C16—C15—C14 | 121.1 (4) |
C3—C4—Br1 | 120.4 (4) | C16—C15—H15 | 119.4 |
C5—C4—Br1 | 119.5 (4) | C14—C15—H15 | 119.4 |
C6—C5—C4 | 120.1 (4) | C15—C16—C11 | 117.3 (4) |
C6—C5—H5 | 120.0 | C15—C16—H16 | 121.4 |
C4—C5—H5 | 120.0 | C11—C16—H16 | 121.4 |
C5—C6—C1 | 121.6 (4) | C17—O2—H2 | 109.4 |
C5—C6—H6 | 119.2 | O2—C17—H17A | 109.5 |
C1—C6—H6 | 119.2 | O2—C17—H17B | 109.5 |
N1—C7—C2 | 125.3 (4) | H17A—C17—H17B | 109.5 |
N1—C7—H7 | 117.3 | O2—C17—H17C | 109.5 |
C2—C7—H7 | 117.3 | H17A—C17—H17C | 109.5 |
N1—C8—C9 | 110.5 (3) | H17B—C17—H17C | 109.5 |
N1—C8—H8A | 109.6 | | |
| | | |
N2—Zn1—O1—C1 | −127.0 (3) | Zn1—N1—C7—C2 | 3.0 (6) |
N1—Zn1—O1—C1 | −31.2 (3) | C3—C2—C7—N1 | 166.7 (4) |
Cl1—Zn1—O1—C1 | 101.9 (3) | C1—C2—C7—N1 | −17.3 (7) |
O1—Zn1—N1—C7 | 16.8 (3) | C7—N1—C8—C9 | −108.6 (4) |
N2—Zn1—N1—C7 | 137.9 (3) | Zn1—N1—C8—C9 | 63.0 (4) |
Cl1—Zn1—N1—C7 | −99.6 (3) | N1—C8—C9—C10 | −61.7 (5) |
O1—Zn1—N1—C8 | −154.5 (3) | C11—N2—C10—N3 | 0.3 (4) |
N2—Zn1—N1—C8 | −33.3 (3) | Zn1—N2—C10—N3 | 176.0 (3) |
Cl1—Zn1—N1—C8 | 89.2 (3) | C11—N2—C10—C9 | 179.0 (4) |
O1—Zn1—N2—C10 | 99.8 (3) | Zn1—N2—C10—C9 | −5.3 (6) |
N1—Zn1—N2—C10 | 4.4 (3) | C12—N3—C10—N2 | 0.0 (5) |
Cl1—Zn1—N2—C10 | −130.8 (3) | C12—N3—C10—C9 | −178.8 (3) |
O1—Zn1—N2—C11 | −85.4 (3) | C8—C9—C10—N2 | 32.4 (6) |
N1—Zn1—N2—C11 | 179.2 (3) | C8—C9—C10—N3 | −149.0 (4) |
Cl1—Zn1—N2—C11 | 44.0 (3) | C10—N2—C11—C16 | 178.6 (4) |
Zn1—O1—C1—C6 | −154.7 (3) | Zn1—N2—C11—C16 | 3.0 (6) |
Zn1—O1—C1—C2 | 27.3 (5) | C10—N2—C11—C12 | −0.4 (4) |
O1—C1—C2—C3 | 176.5 (4) | Zn1—N2—C11—C12 | −176.0 (3) |
C6—C1—C2—C3 | −1.5 (6) | C10—N3—C12—C13 | −179.4 (4) |
O1—C1—C2—C7 | 0.6 (6) | C10—N3—C12—C11 | −0.2 (4) |
C6—C1—C2—C7 | −177.4 (4) | C16—C11—C12—C13 | 0.6 (6) |
C1—C2—C3—C4 | 2.3 (6) | N2—C11—C12—C13 | 179.7 (4) |
C7—C2—C3—C4 | 178.4 (4) | C16—C11—C12—N3 | −178.7 (4) |
C2—C3—C4—C5 | −1.6 (7) | N2—C11—C12—N3 | 0.4 (4) |
C2—C3—C4—Br1 | −179.4 (3) | N3—C12—C13—C14 | 178.4 (4) |
C3—C4—C5—C6 | 0.0 (7) | C11—C12—C13—C14 | −0.7 (6) |
Br1—C4—C5—C6 | 177.9 (3) | C12—C13—C14—C15 | 0.0 (7) |
C4—C5—C6—C1 | 0.7 (7) | C13—C14—C15—C16 | 0.8 (7) |
O1—C1—C6—C5 | −178.1 (4) | C14—C15—C16—C11 | −0.8 (7) |
C2—C1—C6—C5 | 0.1 (6) | N2—C11—C16—C15 | −178.7 (4) |
C8—N1—C7—C2 | 174.0 (4) | C12—C11—C16—C15 | 0.1 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.82 | 1.84 | 2.655 (4) | 172 |
N3—H3A···O2i | 0.86 | 1.88 | 2.716 (4) | 163 |
C6—H6···Cl1ii | 0.93 | 2.83 | 3.600 (5) | 141 |
C8—H8B···Cl1iii | 0.97 | 2.88 | 3.589 (4) | 131 |
C14—H14···Cl1iv | 0.93 | 2.82 | 3.698 (4) | 159 |
Symmetry codes: (i) −x+1, −y, −z−1; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z−1/2; (iv) x, −y−1/2, z−1/2. |