Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026669/xu2261sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026669/xu2261Isup2.hkl |
CCDC reference: 654713
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.027
- wR factor = 0.078
- Data-to-parameter ratio = 20.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
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 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1 (2) 1.92 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
A mixture of N,N-dibenzylglycine (10.2 g, 40 mmol) and o-phenylenediamine (4.32 g, 40 mmol) in 70 ml e thanediol was reflux for 16 h. The mixture was cooled to room temperature and added in hot water. The mixture was constantly stirred until brown solid was obtained and then filtered. The solid was purified by recrystallized from ethanol-water solution to get ligand L. The L (0.0654 g, 0.2 mmol) dissolved in hot ethanol (10 ml) was added to a hot ethanol solution (5 ml) of cadmium chloride (0.0457 g, 0.2 mmol). The mixture was stirred at room temperature for 30 min in air and filtered. Crystals suitable for X-ray diffraction were obtained by slow evaporation of the ethanol solution; yield 78%.
All H-atoms bound to carbon were refined using a riding model with C—H = 0.93–0.97 Å, Uiso(H) = 1.2Ueq(C) for aromatic and CH2, Uiso(H) = 1.5Ueq(C) for CH3. The imino and hydroxy H atoms were located in a difference Fourier map and refined in riding mode with Uiso(H) = 1.5Ueq(O,N). The C23—C24 bond distance restraint was used in the refinement for the lattice solvent molecule.
As part of an investigation of the coordination chemistry of cadmium compounds, we present here the preparation and crystal structure of the title compound.
The title compound is composed of CdII cations, Cl- anions, 1H-benzo[d]imidazol-2-yl)-N,N-dibenzylmethanamine (L) and solvent ethanol molecules. It is a centrosymmetric dimer (Fig. 1). Two CdII cations are bridged by two Cl- anions to form a binuclear compound. Each Cd cation shows a distorted tetragonal pyramid geometry formed by three Cl- anions and two N atoms of L. The Cd—N1 and Cd—N2 bond distances (Table 1) are shorter than the values in the literature (Choi & Jeon, 2003; Huang et al., 1998). The Cd—N2 bond distance is much shorter than the Cd—N1 bond distance, indicating comparatively strong coordination. There are hydrogen-bonding interactions in the crystal (Table 2), forming a two-dimensional supramolecular structure (Fig. 2). In addition, solvent ethanol molecules participate in hydrogen-bonding interactions.
The Cd—N1 and Cd—N2 bond distances of 2.4636 (16) and 2.2819 (16) Å are shorter than those found in the literature (Choi & Jeon, 2003; Huang et al., 1998).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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: SHELXL97.
[Cd2Cl4(C22H21N3)2]·2C2H6O | F(000) = 1128 |
Mr = 1113.58 | Dx = 1.491 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 5067 reflections |
a = 12.6360 (9) Å | θ = 1.9–28.3° |
b = 13.362 (1) Å | µ = 1.12 mm−1 |
c = 15.0200 (11) Å | T = 293 K |
β = 101.955 (5)° | Block, colorless |
V = 2481.0 (3) Å3 | 0.44 × 0.32 × 0.19 mm |
Z = 2 |
Bruker APEX CCD area-detector diffractometer | 5827 independent reflections |
Radiation source: fine-focus sealed tube | 5067 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.659, Tmax = 0.812 | k = −16→15 |
15017 measured reflections | l = −16→20 |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0459P)2 + 0.1798P] where P = (Fo2 + 2Fc2)/3 |
5827 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 0.33 e Å−3 |
1 restraint | Δρmin = −0.69 e Å−3 |
[Cd2Cl4(C22H21N3)2]·2C2H6O | V = 2481.0 (3) Å3 |
Mr = 1113.58 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.6360 (9) Å | µ = 1.12 mm−1 |
b = 13.362 (1) Å | T = 293 K |
c = 15.0200 (11) Å | 0.44 × 0.32 × 0.19 mm |
β = 101.955 (5)° |
Bruker APEX CCD area-detector diffractometer | 5827 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5067 reflections with I > 2σ(I) |
Tmin = 0.659, Tmax = 0.812 | Rint = 0.022 |
15017 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 1 restraint |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.33 e Å−3 |
5827 reflections | Δρmin = −0.69 e Å−3 |
280 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 | ||
Cd1 | 0.600334 (11) | 0.089731 (12) | 0.069920 (10) | 0.04431 (7) | |
C1 | 1.1986 (2) | 0.0283 (2) | 0.18405 (19) | 0.0673 (7) | |
H1 | 1.2728 | 0.0230 | 0.2064 | 0.081* | |
C2 | 1.1488 (2) | 0.1193 (2) | 0.1788 (2) | 0.0721 (8) | |
H2 | 1.1894 | 0.1764 | 0.1974 | 0.087* | |
C3 | 1.03876 (19) | 0.1275 (2) | 0.14614 (18) | 0.0599 (6) | |
H3 | 1.0061 | 0.1902 | 0.1427 | 0.072* | |
C4 | 0.97679 (17) | 0.04404 (18) | 0.11860 (14) | 0.0475 (5) | |
C5 | 1.02856 (19) | −0.0472 (2) | 0.12327 (19) | 0.0630 (6) | |
H5 | 0.9886 | −0.1045 | 0.1039 | 0.076* | |
C6 | 1.1384 (2) | −0.0549 (2) | 0.1562 (2) | 0.0698 (7) | |
H6 | 1.1717 | −0.1173 | 0.1594 | 0.084* | |
C7 | 0.85601 (17) | 0.0526 (2) | 0.08080 (15) | 0.0509 (5) | |
H7A | 0.8422 | 0.1162 | 0.0494 | 0.061* | |
H7B | 0.8350 | 0.0002 | 0.0360 | 0.061* | |
C8 | 0.79287 (19) | −0.05625 (19) | 0.19035 (17) | 0.0544 (5) | |
H8A | 0.8630 | −0.0635 | 0.2308 | 0.065* | |
H8B | 0.7883 | −0.1055 | 0.1423 | 0.065* | |
C9 | 0.70633 (19) | −0.07780 (16) | 0.24284 (16) | 0.0506 (5) | |
C10 | 0.6041 (2) | −0.10782 (18) | 0.19770 (18) | 0.0554 (6) | |
H10 | 0.5914 | −0.1204 | 0.1355 | 0.067* | |
C11 | 0.7238 (2) | −0.0669 (2) | 0.33619 (17) | 0.0626 (7) | |
H11 | 0.7929 | −0.0511 | 0.3685 | 0.075* | |
C12 | 0.6411 (3) | −0.0787 (2) | 0.3826 (2) | 0.0705 (8) | |
H12 | 0.6544 | −0.0705 | 0.4454 | 0.085* | |
C13 | 0.5391 (3) | −0.1027 (2) | 0.3355 (2) | 0.0679 (7) | |
H13 | 0.4824 | −0.1077 | 0.3660 | 0.082* | |
C14 | 0.5207 (2) | −0.1194 (2) | 0.24375 (19) | 0.0631 (6) | |
H14 | 0.4523 | −0.1384 | 0.2124 | 0.076* | |
C15 | 0.81300 (16) | 0.12627 (18) | 0.21745 (14) | 0.0476 (5) | |
H15A | 0.8329 | 0.1862 | 0.1883 | 0.057* | |
H15B | 0.8747 | 0.1059 | 0.2638 | 0.057* | |
C16 | 0.71965 (16) | 0.14870 (15) | 0.26078 (13) | 0.0423 (4) | |
C17 | 0.55683 (16) | 0.16587 (15) | 0.28049 (14) | 0.0421 (4) | |
C18 | 0.44502 (17) | 0.16698 (18) | 0.27295 (16) | 0.0511 (5) | |
H18 | 0.3979 | 0.1579 | 0.2171 | 0.061* | |
C19 | 0.4073 (2) | 0.1820 (2) | 0.35138 (17) | 0.0596 (6) | |
H19 | 0.3331 | 0.1810 | 0.3487 | 0.072* | |
C20 | 0.4769 (2) | 0.1985 (2) | 0.43447 (17) | 0.0620 (6) | |
H20 | 0.4479 | 0.2095 | 0.4857 | 0.074* | |
C21 | 0.5875 (2) | 0.19919 (19) | 0.44337 (15) | 0.0570 (6) | |
H21 | 0.6339 | 0.2105 | 0.4992 | 0.068* | |
C22 | 0.62618 (17) | 0.18215 (16) | 0.36486 (14) | 0.0452 (4) | |
C23 | 0.8661 (7) | 0.0467 (6) | 0.5860 (4) | 0.222 (4) | |
H23A | 0.8736 | 0.0380 | 0.6504 | 0.332* | |
H23B | 0.8922 | −0.0120 | 0.5605 | 0.332* | |
H23C | 0.7912 | 0.0568 | 0.5585 | 0.332* | |
C24 | 0.9298 (5) | 0.1349 (5) | 0.5682 (3) | 0.154 (2) | |
H24A | 0.9035 | 0.1939 | 0.5944 | 0.184* | |
H24B | 1.0049 | 0.1253 | 0.5978 | 0.184* | |
O1 | 0.92314 (17) | 0.15108 (19) | 0.47359 (14) | 0.0912 (7) | |
H1A | 0.9779 | 0.1834 | 0.4641 | 0.137* | |
Cl1 | 0.64262 (5) | 0.23322 (5) | −0.01913 (5) | 0.06842 (17) | |
Cl2 | 0.39562 (4) | 0.06129 (5) | 0.03986 (4) | 0.05318 (14) | |
N1 | 0.78525 (13) | 0.04571 (14) | 0.14913 (11) | 0.0424 (4) | |
N2 | 0.61827 (13) | 0.14620 (13) | 0.21566 (11) | 0.0422 (4) | |
N3 | 0.72942 (14) | 0.17274 (14) | 0.34891 (11) | 0.0460 (4) | |
H3N | 0.7914 | 0.1705 | 0.3880 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.03532 (10) | 0.05476 (12) | 0.03982 (10) | −0.00554 (6) | 0.00081 (6) | −0.00510 (6) |
C1 | 0.0374 (12) | 0.0806 (19) | 0.0830 (18) | −0.0039 (11) | 0.0106 (11) | 0.0061 (14) |
C2 | 0.0450 (13) | 0.0689 (17) | 0.100 (2) | −0.0172 (12) | 0.0087 (14) | −0.0007 (15) |
C3 | 0.0477 (12) | 0.0529 (13) | 0.0789 (17) | −0.0052 (10) | 0.0130 (12) | 0.0062 (12) |
C4 | 0.0373 (10) | 0.0605 (13) | 0.0457 (11) | −0.0042 (9) | 0.0112 (8) | −0.0043 (10) |
C5 | 0.0441 (12) | 0.0613 (15) | 0.0863 (18) | −0.0067 (11) | 0.0197 (12) | −0.0190 (13) |
C6 | 0.0483 (14) | 0.0669 (16) | 0.098 (2) | 0.0063 (12) | 0.0239 (14) | −0.0003 (15) |
C7 | 0.0378 (11) | 0.0697 (14) | 0.0448 (11) | −0.0048 (10) | 0.0081 (9) | −0.0045 (10) |
C8 | 0.0426 (11) | 0.0557 (13) | 0.0641 (14) | 0.0015 (10) | 0.0093 (10) | 0.0037 (11) |
C9 | 0.0491 (12) | 0.0462 (12) | 0.0548 (13) | 0.0023 (9) | 0.0068 (10) | 0.0096 (9) |
C10 | 0.0546 (14) | 0.0567 (14) | 0.0516 (13) | −0.0081 (10) | 0.0033 (10) | 0.0082 (10) |
C11 | 0.0643 (16) | 0.0635 (15) | 0.0542 (14) | −0.0095 (12) | −0.0010 (12) | 0.0146 (11) |
C12 | 0.089 (2) | 0.0696 (18) | 0.0518 (14) | −0.0160 (14) | 0.0119 (14) | 0.0115 (12) |
C13 | 0.0743 (18) | 0.0622 (16) | 0.0733 (18) | −0.0058 (12) | 0.0292 (15) | 0.0162 (13) |
C14 | 0.0540 (14) | 0.0633 (15) | 0.0700 (16) | −0.0092 (12) | 0.0084 (12) | 0.0173 (13) |
C15 | 0.0356 (10) | 0.0579 (12) | 0.0464 (11) | −0.0085 (9) | 0.0016 (8) | −0.0071 (10) |
C16 | 0.0376 (10) | 0.0461 (11) | 0.0411 (10) | −0.0067 (8) | 0.0033 (8) | −0.0038 (8) |
C17 | 0.0416 (10) | 0.0417 (10) | 0.0432 (10) | −0.0036 (8) | 0.0091 (8) | −0.0013 (8) |
C18 | 0.0422 (11) | 0.0564 (13) | 0.0547 (12) | −0.0059 (9) | 0.0099 (9) | −0.0063 (10) |
C19 | 0.0518 (13) | 0.0645 (15) | 0.0681 (15) | −0.0066 (11) | 0.0249 (12) | −0.0020 (12) |
C20 | 0.0731 (16) | 0.0662 (15) | 0.0538 (14) | −0.0031 (12) | 0.0296 (12) | 0.0013 (11) |
C21 | 0.0696 (15) | 0.0607 (14) | 0.0409 (11) | −0.0031 (11) | 0.0118 (10) | −0.0010 (10) |
C22 | 0.0507 (11) | 0.0418 (11) | 0.0426 (10) | −0.0052 (9) | 0.0085 (9) | 0.0009 (8) |
C23 | 0.292 (10) | 0.265 (9) | 0.113 (5) | −0.084 (8) | 0.052 (5) | 0.021 (5) |
C24 | 0.159 (5) | 0.199 (6) | 0.085 (3) | −0.056 (4) | −0.017 (3) | 0.013 (3) |
O1 | 0.0719 (13) | 0.1151 (19) | 0.0731 (13) | −0.0186 (12) | −0.0158 (10) | 0.0113 (13) |
Cl1 | 0.0608 (4) | 0.0701 (4) | 0.0716 (4) | −0.0080 (3) | 0.0074 (3) | 0.0155 (3) |
Cl2 | 0.0355 (3) | 0.0729 (4) | 0.0502 (3) | −0.0067 (2) | 0.0067 (2) | −0.0181 (3) |
N1 | 0.0341 (8) | 0.0499 (10) | 0.0420 (9) | −0.0038 (7) | 0.0050 (7) | −0.0029 (7) |
N2 | 0.0366 (8) | 0.0493 (10) | 0.0392 (8) | −0.0061 (7) | 0.0044 (7) | −0.0041 (7) |
N3 | 0.0422 (9) | 0.0542 (11) | 0.0384 (9) | −0.0065 (7) | 0.0015 (7) | −0.0031 (7) |
Cd1—Cl1 | 2.4591 (7) | C13—C14 | 1.367 (4) |
Cd1—Cl2 | 2.5604 (6) | C13—H13 | 0.9300 |
Cd1—Cl2i | 2.6132 (6) | C14—H14 | 0.9300 |
Cd1—N1 | 2.4636 (16) | C15—N1 | 1.478 (3) |
Cd1—N2 | 2.2819 (16) | C15—C16 | 1.491 (3) |
C1—C6 | 1.363 (4) | C15—H15A | 0.9700 |
C1—C2 | 1.365 (4) | C15—H15B | 0.9700 |
C1—H1 | 0.9300 | C16—N2 | 1.320 (2) |
C2—C3 | 1.380 (4) | C16—N3 | 1.343 (2) |
C2—H2 | 0.9300 | C17—N2 | 1.390 (2) |
C3—C4 | 1.376 (3) | C17—C18 | 1.394 (3) |
C3—H3 | 0.9300 | C17—C22 | 1.400 (3) |
C4—C5 | 1.378 (3) | C18—C19 | 1.374 (3) |
C4—C7 | 1.518 (3) | C18—H18 | 0.9300 |
C5—C6 | 1.377 (4) | C19—C20 | 1.387 (3) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C20—C21 | 1.376 (3) |
C7—N1 | 1.497 (3) | C20—H20 | 0.9300 |
C7—H7A | 0.9700 | C21—C22 | 1.386 (3) |
C7—H7B | 0.9700 | C21—H21 | 0.9300 |
C8—N1 | 1.491 (3) | C22—N3 | 1.380 (3) |
C8—C9 | 1.503 (3) | C23—C24 | 1.483 (7) |
C8—H8A | 0.9700 | C23—H23A | 0.9600 |
C8—H8B | 0.9700 | C23—H23B | 0.9600 |
C9—C11 | 1.381 (3) | C23—H23C | 0.9600 |
C9—C10 | 1.388 (3) | C24—O1 | 1.422 (5) |
C10—C14 | 1.384 (4) | C24—H24A | 0.9700 |
C10—H10 | 0.9300 | C24—H24B | 0.9700 |
C11—C12 | 1.381 (4) | O1—H1A | 0.8518 |
C11—H11 | 0.9300 | Cl2—Cd1i | 2.6132 (6) |
C12—C13 | 1.374 (4) | N3—H3N | 0.8763 |
C12—H12 | 0.9300 | ||
N2—Cd1—Cl1 | 105.92 (5) | C13—C14—H14 | 120.1 |
N2—Cd1—N1 | 73.73 (6) | C10—C14—H14 | 120.1 |
Cl1—Cd1—N1 | 99.07 (4) | N1—C15—C16 | 110.73 (16) |
N2—Cd1—Cl2 | 96.56 (4) | N1—C15—H15A | 109.5 |
Cl1—Cd1—Cl2 | 110.19 (2) | C16—C15—H15A | 109.5 |
N1—Cd1—Cl2 | 150.72 (5) | N1—C15—H15B | 109.5 |
N2—Cd1—Cl2i | 148.17 (5) | C16—C15—H15B | 109.5 |
Cl1—Cd1—Cl2i | 102.95 (2) | H15A—C15—H15B | 108.1 |
N1—Cd1—Cl2i | 88.84 (4) | N2—C16—N3 | 113.18 (19) |
Cl2—Cd1—Cl2i | 85.712 (19) | N2—C16—C15 | 122.84 (18) |
C6—C1—C2 | 119.2 (2) | N3—C16—C15 | 123.98 (18) |
C6—C1—H1 | 120.4 | N2—C17—C18 | 130.45 (19) |
C2—C1—H1 | 120.4 | N2—C17—C22 | 109.12 (17) |
C1—C2—C3 | 120.7 (3) | C18—C17—C22 | 120.37 (19) |
C1—C2—H2 | 119.6 | C19—C18—C17 | 117.2 (2) |
C3—C2—H2 | 119.6 | C19—C18—H18 | 121.4 |
C4—C3—C2 | 120.7 (3) | C17—C18—H18 | 121.4 |
C4—C3—H3 | 119.6 | C18—C19—C20 | 121.8 (2) |
C2—C3—H3 | 119.6 | C18—C19—H19 | 119.1 |
C3—C4—C5 | 117.9 (2) | C20—C19—H19 | 119.1 |
C3—C4—C7 | 121.1 (2) | C21—C20—C19 | 122.0 (2) |
C5—C4—C7 | 121.0 (2) | C21—C20—H20 | 119.0 |
C6—C5—C4 | 121.1 (2) | C19—C20—H20 | 119.0 |
C6—C5—H5 | 119.4 | C20—C21—C22 | 116.5 (2) |
C4—C5—H5 | 119.4 | C20—C21—H21 | 121.7 |
C1—C6—C5 | 120.4 (3) | C22—C21—H21 | 121.7 |
C1—C6—H6 | 119.8 | N3—C22—C21 | 132.5 (2) |
C5—C6—H6 | 119.8 | N3—C22—C17 | 105.40 (17) |
N1—C7—C4 | 115.83 (17) | C21—C22—C17 | 122.0 (2) |
N1—C7—H7A | 108.3 | C24—C23—H23A | 109.5 |
C4—C7—H7A | 108.3 | C24—C23—H23B | 109.5 |
N1—C7—H7B | 108.3 | H23A—C23—H23B | 109.5 |
C4—C7—H7B | 108.3 | C24—C23—H23C | 109.5 |
H7A—C7—H7B | 107.4 | H23A—C23—H23C | 109.5 |
N1—C8—C9 | 113.67 (19) | H23B—C23—H23C | 109.5 |
N1—C8—H8A | 108.8 | O1—C24—C23 | 112.2 (4) |
C9—C8—H8A | 108.8 | O1—C24—H24A | 109.2 |
N1—C8—H8B | 108.8 | C23—C24—H24A | 109.2 |
C9—C8—H8B | 108.8 | O1—C24—H24B | 109.2 |
H8A—C8—H8B | 107.7 | C23—C24—H24B | 109.2 |
C11—C9—C10 | 117.6 (2) | H24A—C24—H24B | 107.9 |
C11—C9—C8 | 122.1 (2) | C24—O1—H1A | 111.3 |
C10—C9—C8 | 120.3 (2) | Cd1—Cl2—Cd1i | 94.288 (19) |
C14—C10—C9 | 121.1 (2) | C15—N1—C8 | 113.04 (18) |
C14—C10—H10 | 119.5 | C15—N1—C7 | 109.96 (16) |
C9—C10—H10 | 119.5 | C8—N1—C7 | 110.16 (17) |
C12—C11—C9 | 121.4 (3) | C15—N1—Cd1 | 103.08 (12) |
C12—C11—H11 | 119.3 | C8—N1—Cd1 | 113.07 (12) |
C9—C11—H11 | 119.3 | C7—N1—Cd1 | 107.19 (12) |
C13—C12—C11 | 119.6 (3) | C16—N2—C17 | 105.01 (16) |
C13—C12—H12 | 120.2 | C16—N2—Cd1 | 113.20 (13) |
C11—C12—H12 | 120.2 | C17—N2—Cd1 | 140.84 (12) |
C14—C13—C12 | 120.2 (3) | C16—N3—C22 | 107.20 (16) |
C14—C13—H13 | 119.9 | C16—N3—H3N | 122.6 |
C12—C13—H13 | 119.9 | C22—N3—H3N | 129.2 |
C13—C14—C10 | 119.9 (3) | ||
C6—C1—C2—C3 | 0.3 (5) | C16—C15—N1—Cd1 | 42.3 (2) |
C1—C2—C3—C4 | 0.3 (4) | C9—C8—N1—C15 | 70.0 (2) |
C2—C3—C4—C5 | −1.1 (4) | C9—C8—N1—C7 | −166.53 (19) |
C2—C3—C4—C7 | −178.7 (2) | C9—C8—N1—Cd1 | −46.6 (2) |
C3—C4—C5—C6 | 1.3 (4) | C4—C7—N1—C15 | 59.5 (3) |
C7—C4—C5—C6 | 179.0 (2) | C4—C7—N1—C8 | −65.7 (2) |
C2—C1—C6—C5 | −0.1 (4) | C4—C7—N1—Cd1 | 170.91 (17) |
C4—C5—C6—C1 | −0.7 (4) | N2—Cd1—N1—C15 | −30.53 (12) |
C3—C4—C7—N1 | −90.2 (3) | Cl1—Cd1—N1—C15 | 73.52 (13) |
C5—C4—C7—N1 | 92.3 (3) | Cl2—Cd1—N1—C15 | −104.44 (14) |
N1—C8—C9—C11 | −97.0 (3) | Cl2i—Cd1—N1—C15 | 176.45 (12) |
N1—C8—C9—C10 | 81.7 (3) | N2—Cd1—N1—C8 | 91.85 (14) |
C11—C9—C10—C14 | 4.5 (4) | Cl1—Cd1—N1—C8 | −164.09 (13) |
C8—C9—C10—C14 | −174.2 (2) | Cl2—Cd1—N1—C8 | 17.94 (19) |
C10—C9—C11—C12 | −4.2 (4) | Cl2i—Cd1—N1—C8 | −61.17 (14) |
C8—C9—C11—C12 | 174.4 (2) | N2—Cd1—N1—C7 | −146.56 (15) |
C9—C11—C12—C13 | 0.5 (4) | Cl1—Cd1—N1—C7 | −42.50 (14) |
C11—C12—C13—C14 | 3.0 (4) | Cl2—Cd1—N1—C7 | 139.53 (12) |
C12—C13—C14—C10 | −2.7 (4) | Cl2i—Cd1—N1—C7 | 60.42 (13) |
C9—C10—C14—C13 | −1.1 (4) | N3—C16—N2—C17 | −2.8 (2) |
N1—C15—C16—N2 | −36.4 (3) | C15—C16—N2—C17 | 176.9 (2) |
N1—C15—C16—N3 | 143.2 (2) | N3—C16—N2—Cd1 | −174.02 (14) |
N2—C17—C18—C19 | 175.3 (2) | C15—C16—N2—Cd1 | 5.6 (3) |
C22—C17—C18—C19 | −1.6 (3) | C18—C17—N2—C16 | −175.9 (2) |
C17—C18—C19—C20 | 2.0 (4) | C22—C17—N2—C16 | 1.3 (2) |
C18—C19—C20—C21 | −1.1 (4) | C18—C17—N2—Cd1 | −8.7 (4) |
C19—C20—C21—C22 | −0.2 (4) | C22—C17—N2—Cd1 | 168.51 (16) |
C20—C21—C22—N3 | −176.4 (2) | Cl1—Cd1—N2—C16 | −80.52 (14) |
C20—C21—C22—C17 | 0.5 (3) | N1—Cd1—N2—C16 | 14.50 (14) |
N2—C17—C22—N3 | 0.5 (2) | Cl2—Cd1—N2—C16 | 166.27 (14) |
C18—C17—C22—N3 | 178.0 (2) | Cl2i—Cd1—N2—C16 | 73.84 (17) |
N2—C17—C22—C21 | −177.1 (2) | Cl1—Cd1—N2—C17 | 112.9 (2) |
C18—C17—C22—C21 | 0.4 (3) | N1—Cd1—N2—C17 | −152.0 (2) |
N2—Cd1—Cl2—Cd1i | −148.11 (5) | Cl2—Cd1—N2—C17 | −0.3 (2) |
Cl1—Cd1—Cl2—Cd1i | 102.23 (3) | Cl2i—Cd1—N2—C17 | −92.7 (2) |
N1—Cd1—Cl2—Cd1i | −79.91 (9) | N2—C16—N3—C22 | 3.2 (2) |
Cl2i—Cd1—Cl2—Cd1i | 0.0 | C15—C16—N3—C22 | −176.5 (2) |
C16—C15—N1—C8 | −80.2 (2) | C21—C22—N3—C16 | 175.1 (2) |
C16—C15—N1—C7 | 156.29 (18) | C17—C22—N3—C16 | −2.1 (2) |
Symmetry code: (i) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···Cl1ii | 0.85 | 2.33 | 3.157 (2) | 164 |
N3—H3N···O1 | 0.88 | 1.90 | 2.772 (3) | 174 |
Symmetry code: (ii) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cd2Cl4(C22H21N3)2]·2C2H6O |
Mr | 1113.58 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 12.6360 (9), 13.362 (1), 15.0200 (11) |
β (°) | 101.955 (5) |
V (Å3) | 2481.0 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.12 |
Crystal size (mm) | 0.44 × 0.32 × 0.19 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.659, 0.812 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15017, 5827, 5067 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.078, 1.05 |
No. of reflections | 5827 |
No. of parameters | 280 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.69 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.
Cd1—Cl1 | 2.4591 (7) | Cd1—N1 | 2.4636 (16) |
Cd1—Cl2 | 2.5604 (6) | Cd1—N2 | 2.2819 (16) |
Cd1—Cl2i | 2.6132 (6) | ||
N2—Cd1—Cl1 | 105.92 (5) | N1—Cd1—Cl2 | 150.72 (5) |
N2—Cd1—N1 | 73.73 (6) | N2—Cd1—Cl2i | 148.17 (5) |
Cl1—Cd1—N1 | 99.07 (4) | Cl1—Cd1—Cl2i | 102.95 (2) |
N2—Cd1—Cl2 | 96.56 (4) | N1—Cd1—Cl2i | 88.84 (4) |
Cl1—Cd1—Cl2 | 110.19 (2) | Cl2—Cd1—Cl2i | 85.712 (19) |
Symmetry code: (i) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···Cl1ii | 0.85 | 2.33 | 3.157 (2) | 164 |
N3—H3N···O1 | 0.88 | 1.90 | 2.772 (3) | 174 |
Symmetry code: (ii) x+1/2, −y+1/2, z+1/2. |
As part of an investigation of the coordination chemistry of cadmium compounds, we present here the preparation and crystal structure of the title compound.
The title compound is composed of CdII cations, Cl- anions, 1H-benzo[d]imidazol-2-yl)-N,N-dibenzylmethanamine (L) and solvent ethanol molecules. It is a centrosymmetric dimer (Fig. 1). Two CdII cations are bridged by two Cl- anions to form a binuclear compound. Each Cd cation shows a distorted tetragonal pyramid geometry formed by three Cl- anions and two N atoms of L. The Cd—N1 and Cd—N2 bond distances (Table 1) are shorter than the values in the literature (Choi & Jeon, 2003; Huang et al., 1998). The Cd—N2 bond distance is much shorter than the Cd—N1 bond distance, indicating comparatively strong coordination. There are hydrogen-bonding interactions in the crystal (Table 2), forming a two-dimensional supramolecular structure (Fig. 2). In addition, solvent ethanol molecules participate in hydrogen-bonding interactions.