Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022829/sj2317sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022829/sj2317Isup2.hkl |
CCDC reference: 650678
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.111
- Data-to-parameter ratio = 26.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.56 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1A (2) 2.05 PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1B (2) 2.02
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 5 Informative message, check
The title compound (I) was synthesized by adding 5-chloro-2-hydroxybenzaldehyde (0.624 g, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in 95% ethanol (20 ml). The mixture was refluxed with stirring for half an hour. Zinc chloride (0.272 g, 2 mmol) in ethanol (10 ml) was then added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was stirred at room temperature for 2 h. A yellow precipitate was obtained, washed with about 5 ml e thanol, dried, and then washed by a copious amount of diethyl ether. This precipitate was then dissolved in 20 ml of pyridine. Yellow single crystals of (I) suitable for x-ray structure determination formed after several days of slow evaporation of the pyridine at room temperature.
All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.96 Å. The Uiso values were constrained to be 1.2Ueq of the carrier atoms. The highest residual peak is located 1.17 Å from Cl1B and the deepest hole is located 0.73 Å from Zn1A.
Schiff base ligands have played an important role in the development of coordination chemistry as they readily form stable complexes with most transition metal ions (Pal et al., 2005). It is also well known that zinc complexes with Schiff-bases are important in biological systems and coordination chemistry (Collinson & Fenton, 1996; Tarafder, Chew et al., 2002; Tarafder, Jin et al., 2002). Recently, we reported the crystal structure of aqua{2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(4-methoxyphenolato)- κ4O,O',N,N'}zinc(II), (II), derived from a related Schiff base ligand (Eltayeb et al., 2007). As an extension of our investigations of the structure of Schiff base zinc(II) complexes, the title mononuclear zinc(II) complex, (I) is reported here.
Complex (I) is a mononuclear zinc(II) compound (Fig. 1). There are two unique molecules in the asymmetric unit. Each ZnII ion is in a distorted square pyramidal geometry and five-coordinated by two N and two O atoms of a Schiff-base ligand forming the basal plane, and by the N atom of pyridine at the axial position. The bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable to the values in another closely related zinc(II) complex, (II) (Eltayeb et al., 2007). The bond angles around the central metal zinc(II) show some deviation from ideal square pyramidal geometry. The dihedral angles between the pyridine (C21–C25/N3) and C1–C6 or C15–C20 rings are 89.75 (11)° and 74.44 (10)°, respectively in molecule A [88.32 (10)Å and 75.71 (10)° in molecule B].
In the crystal structure of (I) as shown Fig. 2, adjacent molecules are linked through weak C—H···Cl interactions into chains running along the b axis. Between the adjacent chains, there are molecules which are arranged diagonally and are bridging these chains through weak C—H···O interactions. The crystal is stabilized by weak C—H···O intra- and intermolecular interactions (Table 1). C—H···π were also observed; Cg1, Cg2 and Cg3 are the centroids of Zn1A–O1A–C1A–C6A–C7A–N1A, Zn1B–O1B–C1B–C6B–C7B–N1B and C1A–C6A, respectively (Table 1).
For a background to Schiff base coordination complexes, see: Pal et al. (2005); Collinson & Fenton (1996); Tarafder, Chew et al. (2002); Tarafder, Jin et al. (2002). For related literature on values of bond lengths and angles, see: Allen et al. (1987). For related structures, see for example: Humphrey et al. (1999); Eltayeb et al. (2007).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
[Zn(C20H12Cl2N2O2)(C5H5N)] | Z = 4 |
Mr = 527.71 | F(000) = 1072 |
Triclinic, P1 | Dx = 1.606 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9840 (4) Å | Cell parameters from 15712 reflections |
b = 12.6632 (6) Å | θ = 0.9–32.5° |
c = 22.3163 (11) Å | µ = 1.40 mm−1 |
α = 91.574 (3)° | T = 100 K |
β = 94.154 (3)° | Needle, yellow |
γ = 103.791 (3)° | 0.60 × 0.20 × 0.12 mm |
V = 2183.11 (19) Å3 |
Bruker SMART APEX II CCD area-detector diffractometer | 15712 independent reflections |
Radiation source: fine-focus sealed tube | 12030 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
Detector resolution: 8.33 pixels mm-1 | θmax = 32.5°, θmin = 0.9° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −19→19 |
Tmin = 0.489, Tmax = 0.855 | l = −33→33 |
55655 measured reflections |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0438P)2 + 1.047P] where P = (Fo2 + 2Fc2)/3 |
15712 reflections | (Δ/σ)max = 0.001 |
595 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.67 e Å−3 |
[Zn(C20H12Cl2N2O2)(C5H5N)] | γ = 103.791 (3)° |
Mr = 527.71 | V = 2183.11 (19) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.9840 (4) Å | Mo Kα radiation |
b = 12.6632 (6) Å | µ = 1.40 mm−1 |
c = 22.3163 (11) Å | T = 100 K |
α = 91.574 (3)° | 0.60 × 0.20 × 0.12 mm |
β = 94.154 (3)° |
Bruker SMART APEX II CCD area-detector diffractometer | 15712 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 12030 reflections with I > 2σ(I) |
Tmin = 0.489, Tmax = 0.855 | Rint = 0.060 |
55655 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.59 e Å−3 |
15712 reflections | Δρmin = −0.67 e Å−3 |
595 parameters |
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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 | ||
Zn1A | 0.07617 (3) | 0.304165 (17) | 0.886205 (10) | 0.01428 (5) | |
Cl1A | −0.08004 (10) | −0.22912 (5) | 0.72552 (3) | 0.03907 (15) | |
Cl2A | 0.60377 (7) | 0.80907 (4) | 1.03804 (2) | 0.02316 (10) | |
O1A | 0.13688 (18) | 0.22551 (11) | 0.81699 (6) | 0.0176 (3) | |
O2A | 0.24672 (18) | 0.44173 (11) | 0.87359 (6) | 0.0183 (3) | |
N1A | −0.0384 (2) | 0.15259 (13) | 0.92090 (7) | 0.0168 (3) | |
N2A | 0.0915 (2) | 0.34531 (13) | 0.97772 (7) | 0.0150 (3) | |
N3A | −0.1483 (2) | 0.34607 (14) | 0.85123 (7) | 0.0179 (3) | |
C1A | 0.0853 (2) | 0.12367 (15) | 0.79939 (9) | 0.0165 (3) | |
C2A | 0.1296 (3) | 0.09106 (17) | 0.74236 (9) | 0.0209 (4) | |
H2AB | 0.1953 | 0.1431 | 0.7194 | 0.025* | |
C3A | 0.0783 (3) | −0.01512 (18) | 0.72002 (10) | 0.0249 (4) | |
H3AB | 0.1075 | −0.0337 | 0.6822 | 0.030* | |
C4A | −0.0174 (3) | −0.09444 (17) | 0.75420 (10) | 0.0250 (4) | |
C5A | −0.0601 (3) | −0.06862 (16) | 0.81019 (10) | 0.0222 (4) | |
H5AB | −0.1221 | −0.1230 | 0.8327 | 0.027* | |
C6A | −0.0108 (2) | 0.03992 (15) | 0.83404 (9) | 0.0178 (3) | |
C7A | −0.0575 (2) | 0.05834 (15) | 0.89393 (9) | 0.0179 (3) | |
H7AB | −0.1052 | −0.0026 | 0.9149 | 0.021* | |
C8A | −0.0853 (2) | 0.16341 (15) | 0.98018 (9) | 0.0166 (3) | |
C9A | −0.2003 (3) | 0.08306 (16) | 1.00863 (10) | 0.0215 (4) | |
H9AB | −0.2516 | 0.0170 | 0.9881 | 0.026* | |
C10A | −0.2384 (3) | 0.10095 (18) | 1.06700 (10) | 0.0237 (4) | |
H10A | −0.3146 | 0.0468 | 1.0856 | 0.028* | |
C11A | −0.1638 (3) | 0.19910 (18) | 1.09781 (9) | 0.0220 (4) | |
H11A | −0.1872 | 0.2100 | 1.1374 | 0.026* | |
C12A | −0.0538 (3) | 0.28133 (16) | 1.06969 (9) | 0.0194 (4) | |
H12A | −0.0067 | 0.3479 | 1.0902 | 0.023* | |
C13A | −0.0133 (2) | 0.26499 (15) | 1.01086 (9) | 0.0158 (3) | |
C14A | 0.1872 (2) | 0.43397 (15) | 1.00396 (9) | 0.0161 (3) | |
H14A | 0.1856 | 0.4417 | 1.0455 | 0.019* | |
C15A | 0.2958 (2) | 0.52160 (15) | 0.97474 (8) | 0.0153 (3) | |
C16A | 0.3845 (2) | 0.61156 (15) | 1.01271 (9) | 0.0175 (3) | |
H16A | 0.3680 | 0.6115 | 1.0535 | 0.021* | |
C17A | 0.4945 (2) | 0.69887 (15) | 0.99026 (9) | 0.0181 (3) | |
C18A | 0.5231 (3) | 0.69989 (16) | 0.92920 (9) | 0.0195 (4) | |
H18A | 0.5982 | 0.7592 | 0.9142 | 0.023* | |
C19A | 0.4393 (3) | 0.61260 (16) | 0.89141 (9) | 0.0189 (4) | |
H19A | 0.4602 | 0.6140 | 0.8509 | 0.023* | |
C20A | 0.3216 (2) | 0.52012 (15) | 0.91204 (9) | 0.0157 (3) | |
C21A | −0.3028 (3) | 0.2735 (2) | 0.84529 (10) | 0.0243 (4) | |
H21A | −0.3103 | 0.2043 | 0.8595 | 0.029* | |
C22A | −0.4504 (3) | 0.2972 (2) | 0.81903 (11) | 0.0336 (6) | |
H22A | −0.5547 | 0.2447 | 0.8152 | 0.040* | |
C23A | −0.4407 (3) | 0.4002 (3) | 0.79847 (11) | 0.0393 (7) | |
H23A | −0.5387 | 0.4183 | 0.7809 | 0.047* | |
C24A | −0.2821 (4) | 0.4764 (2) | 0.80436 (11) | 0.0353 (6) | |
H24A | −0.2720 | 0.5462 | 0.7908 | 0.042* | |
C25A | −0.1397 (3) | 0.44592 (19) | 0.83093 (9) | 0.0237 (4) | |
H25A | −0.0336 | 0.4967 | 0.8349 | 0.028* | |
Zn1B | 0.24994 (3) | 0.750502 (17) | 0.446624 (10) | 0.01377 (5) | |
Cl1B | 0.53214 (8) | 1.14642 (5) | 0.21623 (3) | 0.03329 (13) | |
Cl2B | 0.45724 (7) | 0.33521 (4) | 0.64416 (2) | 0.02195 (10) | |
O1B | 0.40173 (18) | 0.89342 (11) | 0.43171 (6) | 0.0168 (3) | |
O2B | 0.37564 (19) | 0.72741 (11) | 0.52269 (6) | 0.0189 (3) | |
N1B | 0.1634 (2) | 0.73368 (12) | 0.35419 (7) | 0.0142 (3) | |
N2B | 0.1587 (2) | 0.58051 (13) | 0.43293 (7) | 0.0142 (3) | |
N3B | 0.0454 (2) | 0.80835 (13) | 0.47794 (7) | 0.0160 (3) | |
C1B | 0.4220 (2) | 0.94502 (15) | 0.38263 (9) | 0.0152 (3) | |
C2B | 0.5361 (3) | 1.05123 (16) | 0.38571 (9) | 0.0192 (4) | |
H2BA | 0.5904 | 1.0804 | 0.4228 | 0.023* | |
C3B | 0.5683 (3) | 1.11150 (16) | 0.33587 (10) | 0.0214 (4) | |
H3BA | 0.6427 | 1.1805 | 0.3395 | 0.026* | |
C4B | 0.4892 (3) | 1.06911 (17) | 0.27962 (10) | 0.0222 (4) | |
C5B | 0.3774 (3) | 0.96788 (16) | 0.27388 (9) | 0.0198 (4) | |
H5BA | 0.3252 | 0.9407 | 0.2362 | 0.024* | |
C6B | 0.3405 (2) | 0.90455 (15) | 0.32454 (9) | 0.0163 (3) | |
C7B | 0.2218 (2) | 0.79992 (15) | 0.31328 (9) | 0.0154 (3) | |
H7BA | 0.1841 | 0.7781 | 0.2735 | 0.019* | |
C8B | 0.0507 (2) | 0.63124 (14) | 0.33783 (8) | 0.0135 (3) | |
C9B | −0.0596 (2) | 0.60894 (15) | 0.28505 (8) | 0.0155 (3) | |
H9BA | −0.0655 | 0.6642 | 0.2590 | 0.019* | |
C10B | −0.1604 (2) | 0.50445 (16) | 0.27149 (9) | 0.0181 (3) | |
H10B | −0.2319 | 0.4896 | 0.2360 | 0.022* | |
C11B | −0.1547 (3) | 0.42217 (16) | 0.31074 (9) | 0.0187 (4) | |
H11B | −0.2211 | 0.3520 | 0.3011 | 0.022* | |
C12B | −0.0506 (2) | 0.44382 (15) | 0.36435 (9) | 0.0169 (3) | |
H12B | −0.0498 | 0.3885 | 0.3908 | 0.020* | |
C13B | 0.0531 (2) | 0.54836 (15) | 0.37879 (8) | 0.0142 (3) | |
C14B | 0.1999 (2) | 0.50880 (15) | 0.46748 (8) | 0.0153 (3) | |
H14B | 0.1559 | 0.4361 | 0.4552 | 0.018* | |
C15B | 0.3069 (2) | 0.53088 (15) | 0.52288 (8) | 0.0146 (3) | |
C16B | 0.3296 (2) | 0.43856 (15) | 0.55369 (9) | 0.0162 (3) | |
H16B | 0.2727 | 0.3693 | 0.5383 | 0.019* | |
C17B | 0.4345 (2) | 0.45012 (16) | 0.60595 (8) | 0.0164 (3) | |
C18B | 0.5276 (2) | 0.55356 (17) | 0.62836 (9) | 0.0181 (3) | |
H18B | 0.6021 | 0.5607 | 0.6631 | 0.022* | |
C19B | 0.5087 (2) | 0.64438 (16) | 0.59897 (9) | 0.0179 (3) | |
H19B | 0.5729 | 0.7124 | 0.6140 | 0.021* | |
C20B | 0.3942 (2) | 0.63808 (15) | 0.54630 (8) | 0.0152 (3) | |
C21B | −0.0590 (3) | 0.84549 (17) | 0.43842 (9) | 0.0201 (4) | |
H21B | −0.0387 | 0.8437 | 0.3979 | 0.024* | |
C22B | −0.1952 (3) | 0.88633 (18) | 0.45506 (11) | 0.0257 (4) | |
H22B | −0.2652 | 0.9107 | 0.4261 | 0.031* | |
C23B | −0.2268 (3) | 0.8907 (2) | 0.51480 (11) | 0.0291 (5) | |
H23B | −0.3181 | 0.9176 | 0.5270 | 0.035* | |
C24B | −0.1182 (3) | 0.8536 (2) | 0.55642 (10) | 0.0278 (5) | |
H24B | −0.1354 | 0.8555 | 0.5972 | 0.033* | |
C25B | 0.0159 (3) | 0.81361 (17) | 0.53625 (9) | 0.0209 (4) | |
H25C | 0.0885 | 0.7894 | 0.5643 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1A | 0.01486 (10) | 0.01347 (10) | 0.01347 (10) | 0.00164 (7) | 0.00036 (7) | −0.00008 (7) |
Cl1A | 0.0577 (4) | 0.0196 (3) | 0.0383 (3) | 0.0077 (2) | 0.0031 (3) | −0.0118 (2) |
Cl2A | 0.0251 (2) | 0.0156 (2) | 0.0251 (2) | −0.00055 (16) | −0.00211 (18) | −0.00449 (17) |
O1A | 0.0198 (6) | 0.0153 (6) | 0.0171 (6) | 0.0026 (5) | 0.0025 (5) | −0.0008 (5) |
O2A | 0.0201 (6) | 0.0174 (6) | 0.0141 (6) | −0.0018 (5) | 0.0009 (5) | −0.0014 (5) |
N1A | 0.0170 (7) | 0.0156 (7) | 0.0165 (7) | 0.0018 (5) | 0.0007 (6) | 0.0003 (6) |
N2A | 0.0157 (7) | 0.0138 (7) | 0.0150 (7) | 0.0024 (5) | 0.0010 (5) | 0.0014 (5) |
N3A | 0.0174 (7) | 0.0215 (8) | 0.0156 (7) | 0.0064 (6) | 0.0015 (6) | −0.0031 (6) |
C1A | 0.0147 (8) | 0.0179 (8) | 0.0171 (8) | 0.0061 (6) | −0.0029 (6) | −0.0017 (7) |
C2A | 0.0211 (9) | 0.0235 (9) | 0.0189 (9) | 0.0071 (7) | 0.0021 (7) | −0.0024 (7) |
C3A | 0.0272 (10) | 0.0257 (10) | 0.0234 (10) | 0.0110 (8) | −0.0007 (8) | −0.0077 (8) |
C4A | 0.0297 (10) | 0.0164 (9) | 0.0293 (11) | 0.0085 (7) | −0.0022 (8) | −0.0074 (8) |
C5A | 0.0259 (10) | 0.0152 (8) | 0.0247 (10) | 0.0047 (7) | −0.0017 (8) | −0.0025 (7) |
C6A | 0.0183 (8) | 0.0147 (8) | 0.0201 (9) | 0.0043 (6) | −0.0017 (7) | −0.0002 (7) |
C7A | 0.0190 (8) | 0.0142 (8) | 0.0191 (9) | 0.0025 (6) | −0.0014 (7) | 0.0014 (7) |
C8A | 0.0176 (8) | 0.0158 (8) | 0.0161 (8) | 0.0036 (6) | 0.0002 (6) | 0.0022 (6) |
C9A | 0.0237 (9) | 0.0162 (8) | 0.0233 (10) | 0.0014 (7) | 0.0039 (7) | 0.0031 (7) |
C10A | 0.0249 (10) | 0.0218 (9) | 0.0244 (10) | 0.0029 (7) | 0.0087 (8) | 0.0063 (8) |
C11A | 0.0243 (9) | 0.0251 (10) | 0.0177 (9) | 0.0061 (7) | 0.0071 (7) | 0.0051 (7) |
C12A | 0.0206 (9) | 0.0191 (9) | 0.0183 (9) | 0.0043 (7) | 0.0032 (7) | 0.0007 (7) |
C13A | 0.0141 (7) | 0.0167 (8) | 0.0164 (8) | 0.0033 (6) | 0.0013 (6) | 0.0038 (6) |
C14A | 0.0179 (8) | 0.0163 (8) | 0.0141 (8) | 0.0044 (6) | 0.0008 (6) | 0.0002 (6) |
C15A | 0.0157 (8) | 0.0136 (8) | 0.0166 (8) | 0.0035 (6) | 0.0014 (6) | 0.0000 (6) |
C16A | 0.0192 (8) | 0.0164 (8) | 0.0168 (8) | 0.0047 (6) | 0.0002 (7) | 0.0001 (7) |
C17A | 0.0182 (8) | 0.0142 (8) | 0.0207 (9) | 0.0027 (6) | −0.0019 (7) | −0.0033 (7) |
C18A | 0.0172 (8) | 0.0162 (8) | 0.0237 (10) | 0.0010 (6) | 0.0014 (7) | 0.0014 (7) |
C19A | 0.0197 (8) | 0.0172 (8) | 0.0186 (9) | 0.0014 (7) | 0.0030 (7) | 0.0015 (7) |
C20A | 0.0151 (8) | 0.0154 (8) | 0.0167 (8) | 0.0033 (6) | 0.0018 (6) | 0.0013 (6) |
C21A | 0.0176 (9) | 0.0337 (11) | 0.0204 (10) | 0.0041 (8) | 0.0023 (7) | −0.0041 (8) |
C22A | 0.0175 (9) | 0.0593 (17) | 0.0241 (11) | 0.0113 (10) | −0.0012 (8) | −0.0093 (11) |
C23A | 0.0324 (12) | 0.071 (2) | 0.0242 (11) | 0.0350 (13) | −0.0038 (9) | −0.0073 (12) |
C24A | 0.0454 (14) | 0.0474 (15) | 0.0237 (11) | 0.0317 (12) | 0.0031 (10) | 0.0035 (10) |
C25A | 0.0282 (10) | 0.0273 (10) | 0.0191 (9) | 0.0134 (8) | 0.0017 (8) | 0.0007 (8) |
Zn1B | 0.01546 (10) | 0.01179 (10) | 0.01394 (10) | 0.00336 (7) | 0.00016 (7) | 0.00078 (7) |
Cl1B | 0.0322 (3) | 0.0312 (3) | 0.0329 (3) | −0.0022 (2) | 0.0057 (2) | 0.0176 (2) |
Cl2B | 0.0260 (2) | 0.0213 (2) | 0.0208 (2) | 0.01013 (17) | −0.00032 (17) | 0.00674 (17) |
O1B | 0.0184 (6) | 0.0147 (6) | 0.0163 (6) | 0.0023 (5) | 0.0009 (5) | 0.0009 (5) |
O2B | 0.0241 (7) | 0.0144 (6) | 0.0171 (6) | 0.0045 (5) | −0.0044 (5) | 0.0004 (5) |
N1B | 0.0142 (7) | 0.0117 (6) | 0.0170 (7) | 0.0038 (5) | 0.0012 (5) | 0.0014 (5) |
N2B | 0.0155 (7) | 0.0135 (7) | 0.0133 (7) | 0.0031 (5) | 0.0011 (5) | 0.0004 (5) |
N3B | 0.0160 (7) | 0.0133 (7) | 0.0188 (7) | 0.0029 (5) | 0.0031 (6) | 0.0008 (6) |
C1B | 0.0150 (8) | 0.0135 (8) | 0.0181 (8) | 0.0045 (6) | 0.0030 (6) | 0.0009 (6) |
C2B | 0.0185 (8) | 0.0152 (8) | 0.0229 (9) | 0.0019 (6) | 0.0029 (7) | −0.0008 (7) |
C3B | 0.0190 (9) | 0.0140 (8) | 0.0309 (11) | 0.0015 (6) | 0.0069 (8) | 0.0034 (7) |
C4B | 0.0220 (9) | 0.0200 (9) | 0.0253 (10) | 0.0044 (7) | 0.0062 (7) | 0.0105 (8) |
C5B | 0.0186 (8) | 0.0187 (9) | 0.0218 (9) | 0.0034 (7) | 0.0028 (7) | 0.0041 (7) |
C6B | 0.0153 (8) | 0.0152 (8) | 0.0186 (9) | 0.0035 (6) | 0.0029 (6) | 0.0021 (7) |
C7B | 0.0154 (8) | 0.0158 (8) | 0.0157 (8) | 0.0046 (6) | 0.0016 (6) | 0.0015 (6) |
C8B | 0.0138 (7) | 0.0125 (7) | 0.0139 (8) | 0.0025 (6) | 0.0024 (6) | −0.0007 (6) |
C9B | 0.0171 (8) | 0.0163 (8) | 0.0136 (8) | 0.0047 (6) | 0.0018 (6) | 0.0022 (6) |
C10B | 0.0180 (8) | 0.0201 (9) | 0.0157 (8) | 0.0044 (7) | −0.0009 (6) | −0.0005 (7) |
C11B | 0.0189 (8) | 0.0158 (8) | 0.0197 (9) | 0.0013 (6) | 0.0012 (7) | −0.0018 (7) |
C12B | 0.0190 (8) | 0.0140 (8) | 0.0172 (8) | 0.0026 (6) | 0.0015 (6) | 0.0026 (6) |
C13B | 0.0150 (7) | 0.0150 (8) | 0.0126 (8) | 0.0032 (6) | 0.0017 (6) | 0.0015 (6) |
C14B | 0.0173 (8) | 0.0128 (7) | 0.0153 (8) | 0.0028 (6) | 0.0017 (6) | −0.0004 (6) |
C15B | 0.0146 (7) | 0.0152 (8) | 0.0145 (8) | 0.0041 (6) | 0.0019 (6) | 0.0021 (6) |
C16B | 0.0161 (8) | 0.0164 (8) | 0.0169 (8) | 0.0050 (6) | 0.0032 (6) | 0.0026 (6) |
C17B | 0.0172 (8) | 0.0188 (8) | 0.0153 (8) | 0.0078 (6) | 0.0026 (6) | 0.0045 (7) |
C18B | 0.0177 (8) | 0.0235 (9) | 0.0142 (8) | 0.0076 (7) | −0.0008 (6) | 0.0017 (7) |
C19B | 0.0168 (8) | 0.0187 (8) | 0.0174 (9) | 0.0034 (6) | 0.0001 (6) | −0.0012 (7) |
C20B | 0.0158 (8) | 0.0156 (8) | 0.0143 (8) | 0.0040 (6) | 0.0020 (6) | 0.0009 (6) |
C21B | 0.0206 (9) | 0.0209 (9) | 0.0201 (9) | 0.0079 (7) | 0.0015 (7) | 0.0013 (7) |
C22B | 0.0197 (9) | 0.0245 (10) | 0.0341 (12) | 0.0088 (8) | 0.0008 (8) | −0.0030 (9) |
C23B | 0.0181 (9) | 0.0313 (11) | 0.0367 (12) | 0.0037 (8) | 0.0072 (8) | −0.0120 (9) |
C24B | 0.0257 (10) | 0.0316 (11) | 0.0232 (10) | 0.0003 (8) | 0.0076 (8) | −0.0067 (9) |
C25B | 0.0211 (9) | 0.0195 (9) | 0.0192 (9) | −0.0013 (7) | 0.0030 (7) | −0.0003 (7) |
Zn1A—O1A | 1.9665 (14) | Zn1B—O2B | 1.9734 (14) |
Zn1A—O2A | 1.9798 (13) | Zn1B—O1B | 1.9750 (13) |
Zn1A—N2A | 2.0815 (16) | Zn1B—N3B | 2.0971 (17) |
Zn1A—N3A | 2.0919 (17) | Zn1B—N2B | 2.1076 (16) |
Zn1A—N1A | 2.1138 (16) | Zn1B—N1B | 2.1160 (16) |
Cl1A—C4A | 1.748 (2) | Cl1B—C4B | 1.750 (2) |
Cl2A—C17A | 1.7459 (19) | Cl2B—C17B | 1.7462 (19) |
O1A—C1A | 1.297 (2) | O1B—C1B | 1.291 (2) |
O2A—C20A | 1.294 (2) | O2B—C20B | 1.296 (2) |
N1A—C7A | 1.293 (3) | N1B—C7B | 1.293 (2) |
N1A—C8A | 1.412 (3) | N1B—C8B | 1.413 (2) |
N2A—C14A | 1.295 (2) | N2B—C14B | 1.293 (2) |
N2A—C13A | 1.416 (2) | N2B—C13B | 1.414 (2) |
N3A—C25A | 1.343 (3) | N3B—C21B | 1.341 (3) |
N3A—C21A | 1.347 (3) | N3B—C25B | 1.342 (3) |
C1A—C2A | 1.422 (3) | C1B—C2B | 1.430 (3) |
C1A—C6A | 1.433 (3) | C1B—C6B | 1.431 (3) |
C2A—C3A | 1.377 (3) | C2B—C3B | 1.371 (3) |
C2A—H2AB | 0.9300 | C2B—H2BA | 0.9300 |
C3A—C4A | 1.391 (3) | C3B—C4B | 1.396 (3) |
C3A—H3AB | 0.9300 | C3B—H3BA | 0.9300 |
C4A—C5A | 1.370 (3) | C4B—C5B | 1.373 (3) |
C5A—C6A | 1.414 (3) | C5B—C6B | 1.412 (3) |
C5A—H5AB | 0.9300 | C5B—H5BA | 0.9300 |
C6A—C7A | 1.441 (3) | C6B—C7B | 1.437 (3) |
C7A—H7AB | 0.9300 | C7B—H7BA | 0.9300 |
C8A—C9A | 1.399 (3) | C8B—C9B | 1.398 (3) |
C8A—C13A | 1.413 (3) | C8B—C13B | 1.413 (3) |
C9A—C10A | 1.384 (3) | C9B—C10B | 1.387 (3) |
C9A—H9AB | 0.9300 | C9B—H9BA | 0.9300 |
C10A—C11A | 1.383 (3) | C10B—C11B | 1.386 (3) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—C12A | 1.389 (3) | C11B—C12B | 1.388 (3) |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C13A | 1.396 (3) | C12B—C13B | 1.399 (3) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C14A—C15A | 1.439 (3) | C14B—C15B | 1.432 (3) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.412 (3) | C15B—C16B | 1.414 (3) |
C15A—C20A | 1.429 (3) | C15B—C20B | 1.435 (3) |
C16A—C17A | 1.370 (3) | C16B—C17B | 1.369 (3) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—C18A | 1.398 (3) | C17B—C18B | 1.402 (3) |
C18A—C19A | 1.377 (3) | C18B—C19B | 1.373 (3) |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
C19A—C20A | 1.426 (3) | C19B—C20B | 1.424 (3) |
C19A—H19A | 0.9300 | C19B—H19B | 0.9300 |
C21A—C22A | 1.378 (3) | C21B—C22B | 1.380 (3) |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C22A—C23A | 1.381 (4) | C22B—C23B | 1.377 (3) |
C22A—H22A | 0.9300 | C22B—H22B | 0.9300 |
C23A—C24A | 1.392 (4) | C23B—C24B | 1.391 (4) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
C24A—C25A | 1.385 (3) | C24B—C25B | 1.386 (3) |
C24A—H24A | 0.9300 | C24B—H24B | 0.9300 |
C25A—H25A | 0.9300 | C25B—H25C | 0.9300 |
O1A—Zn1A—O2A | 94.27 (6) | O2B—Zn1B—O1B | 96.46 (6) |
O1A—Zn1A—N2A | 152.35 (6) | O2B—Zn1B—N3B | 101.63 (6) |
O2A—Zn1A—N2A | 90.19 (6) | O1B—Zn1B—N3B | 97.23 (6) |
O1A—Zn1A—N3A | 101.93 (6) | O2B—Zn1B—N2B | 89.26 (6) |
O2A—Zn1A—N3A | 98.92 (7) | O1B—Zn1B—N2B | 153.84 (6) |
N2A—Zn1A—N3A | 104.30 (6) | N3B—Zn1B—N2B | 106.60 (6) |
O1A—Zn1A—N1A | 88.80 (6) | O2B—Zn1B—N1B | 159.13 (6) |
O2A—Zn1A—N1A | 160.78 (6) | O1B—Zn1B—N1B | 88.79 (6) |
N2A—Zn1A—N1A | 78.67 (6) | N3B—Zn1B—N1B | 97.70 (6) |
N3A—Zn1A—N1A | 98.99 (7) | N2B—Zn1B—N1B | 77.66 (6) |
C1A—O1A—Zn1A | 130.17 (13) | C1B—O1B—Zn1B | 130.18 (12) |
C20A—O2A—Zn1A | 129.38 (12) | C20B—O2B—Zn1B | 130.32 (12) |
C7A—N1A—C8A | 121.75 (17) | C7B—N1B—C8B | 120.31 (16) |
C7A—N1A—Zn1A | 125.75 (14) | C7B—N1B—Zn1B | 126.05 (13) |
C8A—N1A—Zn1A | 112.40 (12) | C8B—N1B—Zn1B | 112.91 (11) |
C14A—N2A—C13A | 121.22 (16) | C14B—N2B—C13B | 120.78 (16) |
C14A—N2A—Zn1A | 125.28 (13) | C14B—N2B—Zn1B | 125.35 (13) |
C13A—N2A—Zn1A | 113.50 (12) | C13B—N2B—Zn1B | 113.74 (12) |
C25A—N3A—C21A | 117.93 (19) | C21B—N3B—C25B | 117.53 (18) |
C25A—N3A—Zn1A | 120.16 (14) | C21B—N3B—Zn1B | 119.04 (13) |
C21A—N3A—Zn1A | 121.81 (15) | C25B—N3B—Zn1B | 123.39 (14) |
O1A—C1A—C2A | 118.42 (18) | O1B—C1B—C2B | 118.05 (17) |
O1A—C1A—C6A | 124.65 (18) | O1B—C1B—C6B | 125.45 (16) |
C2A—C1A—C6A | 116.91 (18) | C2B—C1B—C6B | 116.50 (17) |
C3A—C2A—C1A | 122.1 (2) | C3B—C2B—C1B | 122.30 (19) |
C3A—C2A—H2AB | 118.9 | C3B—C2B—H2BA | 118.8 |
C1A—C2A—H2AB | 118.9 | C1B—C2B—H2BA | 118.8 |
C2A—C3A—C4A | 119.7 (2) | C2B—C3B—C4B | 119.90 (18) |
C2A—C3A—H3AB | 120.1 | C2B—C3B—H3BA | 120.0 |
C4A—C3A—H3AB | 120.1 | C4B—C3B—H3BA | 120.0 |
C5A—C4A—C3A | 120.89 (19) | C5B—C4B—C3B | 120.48 (19) |
C5A—C4A—Cl1A | 119.88 (18) | C5B—C4B—Cl1B | 119.99 (17) |
C3A—C4A—Cl1A | 119.21 (17) | C3B—C4B—Cl1B | 119.53 (15) |
C4A—C5A—C6A | 120.6 (2) | C4B—C5B—C6B | 120.79 (19) |
C4A—C5A—H5AB | 119.7 | C4B—C5B—H5BA | 119.6 |
C6A—C5A—H5AB | 119.7 | C6B—C5B—H5BA | 119.6 |
C5A—C6A—C1A | 119.68 (19) | C5B—C6B—C1B | 120.01 (17) |
C5A—C6A—C7A | 116.47 (18) | C5B—C6B—C7B | 116.05 (17) |
C1A—C6A—C7A | 123.82 (17) | C1B—C6B—C7B | 123.94 (17) |
N1A—C7A—C6A | 125.36 (18) | N1B—C7B—C6B | 125.12 (18) |
N1A—C7A—H7AB | 117.3 | N1B—C7B—H7BA | 117.4 |
C6A—C7A—H7AB | 117.3 | C6B—C7B—H7BA | 117.4 |
C9A—C8A—N1A | 124.64 (17) | C9B—C8B—N1B | 124.22 (16) |
C9A—C8A—C13A | 119.23 (18) | C9B—C8B—C13B | 119.84 (16) |
N1A—C8A—C13A | 116.09 (16) | N1B—C8B—C13B | 115.94 (16) |
C10A—C9A—C8A | 120.60 (19) | C10B—C9B—C8B | 120.11 (17) |
C10A—C9A—H9AB | 119.7 | C10B—C9B—H9BA | 119.9 |
C8A—C9A—H9AB | 119.7 | C8B—C9B—H9BA | 119.9 |
C11A—C10A—C9A | 120.23 (19) | C11B—C10B—C9B | 120.19 (18) |
C11A—C10A—H10A | 119.9 | C11B—C10B—H10B | 119.9 |
C9A—C10A—H10A | 119.9 | C9B—C10B—H10B | 119.9 |
C10A—C11A—C12A | 120.09 (19) | C10B—C11B—C12B | 120.42 (17) |
C10A—C11A—H11A | 120.0 | C10B—C11B—H11B | 119.8 |
C12A—C11A—H11A | 120.0 | C12B—C11B—H11B | 119.8 |
C11A—C12A—C13A | 120.62 (19) | C11B—C12B—C13B | 120.42 (17) |
C11A—C12A—H12A | 119.7 | C11B—C12B—H12B | 119.8 |
C13A—C12A—H12A | 119.7 | C13B—C12B—H12B | 119.8 |
C12A—C13A—C8A | 119.17 (17) | C12B—C13B—C8B | 118.95 (16) |
C12A—C13A—N2A | 124.60 (17) | C12B—C13B—N2B | 125.21 (16) |
C8A—C13A—N2A | 116.19 (17) | C8B—C13B—N2B | 115.80 (15) |
N2A—C14A—C15A | 125.94 (18) | N2B—C14B—C15B | 126.11 (17) |
N2A—C14A—H14A | 117.0 | N2B—C14B—H14B | 116.9 |
C15A—C14A—H14A | 117.0 | C15B—C14B—H14B | 116.9 |
C16A—C15A—C20A | 120.06 (17) | C16B—C15B—C14B | 115.75 (16) |
C16A—C15A—C14A | 115.59 (17) | C16B—C15B—C20B | 120.06 (17) |
C20A—C15A—C14A | 124.31 (17) | C14B—C15B—C20B | 124.14 (17) |
C17A—C16A—C15A | 120.92 (18) | C17B—C16B—C15B | 120.67 (18) |
C17A—C16A—H16A | 119.5 | C17B—C16B—H16B | 119.7 |
C15A—C16A—H16A | 119.5 | C15B—C16B—H16B | 119.7 |
C16A—C17A—C18A | 120.47 (18) | C16B—C17B—C18B | 120.48 (17) |
C16A—C17A—Cl2A | 120.21 (16) | C16B—C17B—Cl2B | 119.96 (15) |
C18A—C17A—Cl2A | 119.31 (15) | C18B—C17B—Cl2B | 119.54 (15) |
C19A—C18A—C17A | 119.63 (18) | C19B—C18B—C17B | 119.85 (17) |
C19A—C18A—H18A | 120.2 | C19B—C18B—H18B | 120.1 |
C17A—C18A—H18A | 120.2 | C17B—C18B—H18B | 120.1 |
C18A—C19A—C20A | 122.41 (18) | C18B—C19B—C20B | 122.29 (18) |
C18A—C19A—H19A | 118.8 | C18B—C19B—H19B | 118.9 |
C20A—C19A—H19A | 118.8 | C20B—C19B—H19B | 118.9 |
O2A—C20A—C19A | 118.70 (17) | O2B—C20B—C19B | 119.03 (17) |
O2A—C20A—C15A | 124.80 (16) | O2B—C20B—C15B | 124.47 (17) |
C19A—C20A—C15A | 116.50 (17) | C19B—C20B—C15B | 116.49 (17) |
N3A—C21A—C22A | 122.9 (2) | N3B—C21B—C22B | 123.0 (2) |
N3A—C21A—H21A | 118.6 | N3B—C21B—H21B | 118.5 |
C22A—C21A—H21A | 118.6 | C22B—C21B—H21B | 118.5 |
C21A—C22A—C23A | 118.9 (2) | C23B—C22B—C21B | 119.5 (2) |
C21A—C22A—H22A | 120.6 | C23B—C22B—H22B | 120.3 |
C23A—C22A—H22A | 120.6 | C21B—C22B—H22B | 120.3 |
C22A—C23A—C24A | 119.1 (2) | C22B—C23B—C24B | 118.2 (2) |
C22A—C23A—H23A | 120.5 | C22B—C23B—H23B | 120.9 |
C24A—C23A—H23A | 120.5 | C24B—C23B—H23B | 120.9 |
C25A—C24A—C23A | 118.5 (3) | C25B—C24B—C23B | 119.0 (2) |
C25A—C24A—H24A | 120.7 | C25B—C24B—H24B | 120.5 |
C23A—C24A—H24A | 120.7 | C23B—C24B—H24B | 120.5 |
N3A—C25A—C24A | 122.7 (2) | N3B—C25B—C24B | 122.8 (2) |
N3A—C25A—H25A | 118.6 | N3B—C25B—H25C | 118.6 |
C24A—C25A—H25A | 118.6 | C24B—C25B—H25C | 118.6 |
O2A—Zn1A—O1A—C1A | 173.52 (16) | O2B—Zn1B—O1B—C1B | 160.82 (16) |
N2A—Zn1A—O1A—C1A | 74.9 (2) | N3B—Zn1B—O1B—C1B | −96.53 (17) |
N3A—Zn1A—O1A—C1A | −86.41 (17) | N2B—Zn1B—O1B—C1B | 59.2 (2) |
N1A—Zn1A—O1A—C1A | 12.52 (17) | N1B—Zn1B—O1B—C1B | 1.08 (17) |
O1A—Zn1A—O2A—C20A | −154.74 (17) | O1B—Zn1B—O2B—C20B | −149.62 (17) |
N2A—Zn1A—O2A—C20A | −2.06 (17) | N3B—Zn1B—O2B—C20B | 111.60 (17) |
N3A—Zn1A—O2A—C20A | 102.45 (17) | N2B—Zn1B—O2B—C20B | 4.79 (17) |
N1A—Zn1A—O2A—C20A | −56.1 (3) | N1B—Zn1B—O2B—C20B | −45.9 (3) |
O1A—Zn1A—N1A—C7A | −5.56 (17) | O2B—Zn1B—N1B—C7B | −100.1 (2) |
O2A—Zn1A—N1A—C7A | −105.1 (2) | O1B—Zn1B—N1B—C7B | 4.98 (16) |
N2A—Zn1A—N1A—C7A | −160.76 (18) | N3B—Zn1B—N1B—C7B | 102.11 (16) |
N3A—Zn1A—N1A—C7A | 96.33 (17) | N2B—Zn1B—N1B—C7B | −152.48 (17) |
O1A—Zn1A—N1A—C8A | 170.79 (13) | O2B—Zn1B—N1B—C8B | 70.0 (2) |
O2A—Zn1A—N1A—C8A | 71.2 (2) | O1B—Zn1B—N1B—C8B | 175.10 (13) |
N2A—Zn1A—N1A—C8A | 15.59 (13) | N3B—Zn1B—N1B—C8B | −87.77 (13) |
N3A—Zn1A—N1A—C8A | −87.32 (13) | N2B—Zn1B—N1B—C8B | 17.63 (12) |
O1A—Zn1A—N2A—C14A | 100.08 (19) | O2B—Zn1B—N2B—C14B | −3.12 (16) |
O2A—Zn1A—N2A—C14A | 0.49 (17) | O1B—Zn1B—N2B—C14B | 100.12 (19) |
N3A—Zn1A—N2A—C14A | −98.77 (17) | N3B—Zn1B—N2B—C14B | −105.04 (16) |
N1A—Zn1A—N2A—C14A | 164.72 (17) | N1B—Zn1B—N2B—C14B | 160.49 (17) |
O1A—Zn1A—N2A—C13A | −79.03 (18) | O2B—Zn1B—N2B—C13B | −179.06 (13) |
O2A—Zn1A—N2A—C13A | −178.63 (13) | O1B—Zn1B—N2B—C13B | −75.83 (19) |
N3A—Zn1A—N2A—C13A | 82.11 (14) | N3B—Zn1B—N2B—C13B | 79.01 (13) |
N1A—Zn1A—N2A—C13A | −14.40 (13) | N1B—Zn1B—N2B—C13B | −15.45 (12) |
O1A—Zn1A—N3A—C25A | −98.16 (15) | O2B—Zn1B—N3B—C21B | 172.35 (14) |
O2A—Zn1A—N3A—C25A | −1.84 (16) | O1B—Zn1B—N3B—C21B | 74.19 (15) |
N2A—Zn1A—N3A—C25A | 90.65 (16) | N2B—Zn1B—N3B—C21B | −94.92 (15) |
N1A—Zn1A—N3A—C25A | 171.16 (15) | N1B—Zn1B—N3B—C21B | −15.56 (15) |
O1A—Zn1A—N3A—C21A | 78.24 (16) | O2B—Zn1B—N3B—C25B | −5.46 (16) |
O2A—Zn1A—N3A—C21A | 174.57 (15) | O1B—Zn1B—N3B—C25B | −103.61 (15) |
N2A—Zn1A—N3A—C21A | −92.94 (16) | N2B—Zn1B—N3B—C25B | 87.28 (15) |
N1A—Zn1A—N3A—C21A | −12.43 (16) | N1B—Zn1B—N3B—C25B | 166.64 (15) |
Zn1A—O1A—C1A—C2A | 170.62 (14) | Zn1B—O1B—C1B—C2B | 176.85 (13) |
Zn1A—O1A—C1A—C6A | −10.9 (3) | Zn1B—O1B—C1B—C6B | −3.7 (3) |
O1A—C1A—C2A—C3A | −179.22 (19) | O1B—C1B—C2B—C3B | 178.84 (19) |
C6A—C1A—C2A—C3A | 2.2 (3) | C6B—C1B—C2B—C3B | −0.7 (3) |
C1A—C2A—C3A—C4A | −1.1 (3) | C1B—C2B—C3B—C4B | −0.4 (3) |
C2A—C3A—C4A—C5A | −0.7 (3) | C2B—C3B—C4B—C5B | 0.9 (3) |
C2A—C3A—C4A—Cl1A | −179.45 (17) | C2B—C3B—C4B—Cl1B | −179.64 (17) |
C3A—C4A—C5A—C6A | 1.3 (3) | C3B—C4B—C5B—C6B | −0.2 (3) |
Cl1A—C4A—C5A—C6A | −179.88 (16) | Cl1B—C4B—C5B—C6B | −179.70 (16) |
C4A—C5A—C6A—C1A | −0.2 (3) | C4B—C5B—C6B—C1B | −0.9 (3) |
C4A—C5A—C6A—C7A | −178.3 (2) | C4B—C5B—C6B—C7B | −179.95 (19) |
O1A—C1A—C6A—C5A | −179.97 (19) | O1B—C1B—C6B—C5B | −178.17 (19) |
C2A—C1A—C6A—C5A | −1.5 (3) | C2B—C1B—C6B—C5B | 1.3 (3) |
O1A—C1A—C6A—C7A | −2.1 (3) | O1B—C1B—C6B—C7B | 0.8 (3) |
C2A—C1A—C6A—C7A | 176.47 (19) | C2B—C1B—C6B—C7B | −179.71 (18) |
C8A—N1A—C7A—C6A | −179.00 (18) | C8B—N1B—C7B—C6B | −178.18 (18) |
Zn1A—N1A—C7A—C6A | −3.0 (3) | Zn1B—N1B—C7B—C6B | −8.7 (3) |
C5A—C6A—C7A—N1A | −173.03 (19) | C5B—C6B—C7B—N1B | −175.09 (19) |
C1A—C6A—C7A—N1A | 9.0 (3) | C1B—C6B—C7B—N1B | 5.9 (3) |
C7A—N1A—C8A—C9A | −20.4 (3) | C7B—N1B—C8B—C9B | −27.0 (3) |
Zn1A—N1A—C8A—C9A | 163.06 (17) | Zn1B—N1B—C8B—C9B | 162.22 (15) |
C7A—N1A—C8A—C13A | 161.92 (18) | C7B—N1B—C8B—C13B | 153.22 (18) |
Zn1A—N1A—C8A—C13A | −14.6 (2) | Zn1B—N1B—C8B—C13B | −17.5 (2) |
N1A—C8A—C9A—C10A | 180.0 (2) | N1B—C8B—C9B—C10B | 177.18 (18) |
C13A—C8A—C9A—C10A | −2.4 (3) | C13B—C8B—C9B—C10B | −3.1 (3) |
C8A—C9A—C10A—C11A | 0.4 (3) | C8B—C9B—C10B—C11B | 1.2 (3) |
C9A—C10A—C11A—C12A | 1.8 (3) | C9B—C10B—C11B—C12B | 1.1 (3) |
C10A—C11A—C12A—C13A | −1.9 (3) | C10B—C11B—C12B—C13B | −1.5 (3) |
C11A—C12A—C13A—C8A | −0.2 (3) | C11B—C12B—C13B—C8B | −0.3 (3) |
C11A—C12A—C13A—N2A | 177.24 (19) | C11B—C12B—C13B—N2B | 177.46 (18) |
C9A—C8A—C13A—C12A | 2.3 (3) | C9B—C8B—C13B—C12B | 2.6 (3) |
N1A—C8A—C13A—C12A | −179.89 (18) | N1B—C8B—C13B—C12B | −177.65 (17) |
C9A—C8A—C13A—N2A | −175.29 (18) | C9B—C8B—C13B—N2B | −175.37 (17) |
N1A—C8A—C13A—N2A | 2.5 (3) | N1B—C8B—C13B—N2B | 4.4 (2) |
C14A—N2A—C13A—C12A | 14.5 (3) | C14B—N2B—C13B—C12B | 17.1 (3) |
Zn1A—N2A—C13A—C12A | −166.32 (16) | Zn1B—N2B—C13B—C12B | −166.78 (16) |
C14A—N2A—C13A—C8A | −168.00 (18) | C14B—N2B—C13B—C8B | −165.12 (17) |
Zn1A—N2A—C13A—C8A | 11.1 (2) | Zn1B—N2B—C13B—C8B | 11.0 (2) |
C13A—N2A—C14A—C15A | −178.79 (18) | C13B—N2B—C14B—C15B | 179.31 (17) |
Zn1A—N2A—C14A—C15A | 2.2 (3) | Zn1B—N2B—C14B—C15B | 3.6 (3) |
N2A—C14A—C15A—C16A | 178.22 (19) | N2B—C14B—C15B—C16B | 178.27 (18) |
N2A—C14A—C15A—C20A | −4.0 (3) | N2B—C14B—C15B—C20B | −4.3 (3) |
C20A—C15A—C16A—C17A | 0.7 (3) | C14B—C15B—C16B—C17B | 177.56 (17) |
C14A—C15A—C16A—C17A | 178.59 (18) | C20B—C15B—C16B—C17B | 0.0 (3) |
C15A—C16A—C17A—C18A | −0.9 (3) | C15B—C16B—C17B—C18B | −3.0 (3) |
C15A—C16A—C17A—Cl2A | −179.71 (15) | C15B—C16B—C17B—Cl2B | 178.64 (14) |
C16A—C17A—C18A—C19A | 0.3 (3) | C16B—C17B—C18B—C19B | 2.4 (3) |
Cl2A—C17A—C18A—C19A | 179.07 (16) | Cl2B—C17B—C18B—C19B | −179.17 (15) |
C17A—C18A—C19A—C20A | 0.6 (3) | C17B—C18B—C19B—C20B | 1.1 (3) |
Zn1A—O2A—C20A—C19A | −179.07 (14) | Zn1B—O2B—C20B—C19B | 172.92 (13) |
Zn1A—O2A—C20A—C15A | 1.0 (3) | Zn1B—O2B—C20B—C15B | −6.8 (3) |
C18A—C19A—C20A—O2A | 179.36 (19) | C18B—C19B—C20B—O2B | 176.31 (18) |
C18A—C19A—C20A—C15A | −0.7 (3) | C18B—C19B—C20B—C15B | −3.9 (3) |
C16A—C15A—C20A—O2A | 179.99 (19) | C16B—C15B—C20B—O2B | −176.93 (18) |
C14A—C15A—C20A—O2A | 2.3 (3) | C14B—C15B—C20B—O2B | 5.7 (3) |
C16A—C15A—C20A—C19A | 0.1 (3) | C16B—C15B—C20B—C19B | 3.3 (3) |
C14A—C15A—C20A—C19A | −177.60 (18) | C14B—C15B—C20B—C19B | −174.00 (17) |
C25A—N3A—C21A—C22A | 0.6 (3) | C25B—N3B—C21B—C22B | −1.2 (3) |
Zn1A—N3A—C21A—C22A | −175.93 (17) | Zn1B—N3B—C21B—C22B | −179.15 (16) |
N3A—C21A—C22A—C23A | −0.8 (3) | N3B—C21B—C22B—C23B | 0.5 (3) |
C21A—C22A—C23A—C24A | 0.6 (4) | C21B—C22B—C23B—C24B | 0.2 (3) |
C22A—C23A—C24A—C25A | −0.2 (4) | C22B—C23B—C24B—C25B | −0.3 (3) |
C21A—N3A—C25A—C24A | −0.1 (3) | C21B—N3B—C25B—C24B | 1.2 (3) |
Zn1A—N3A—C25A—C24A | 176.41 (17) | Zn1B—N3B—C25B—C24B | 178.99 (15) |
C23A—C24A—C25A—N3A | 0.0 (4) | C23B—C24B—C25B—N3B | −0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9B—H9BA···O1Ai | 0.93 | 2.35 | 3.261 (2) | 167 |
C21B—H21B···N1B | 0.93 | 2.59 | 3.198 (3) | 123 |
C22A—H22A···O1Aii | 0.93 | 2.42 | 3.199 (3) | 141 |
C25A—H25A···O2A | 0.93 | 2.60 | 3.175 (3) | 121 |
C5B—H5BA···Cg3i | 0.93 | 3.06 | 3.463 (3) | 108 |
C21A—H21A···Cg1 | 0.93 | 2.97 | 3.397 (3) | 109 |
C21B—H21B···Cg2 | 0.93 | 2.80 | 3.301 (2) | 115 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C20H12Cl2N2O2)(C5H5N)] |
Mr | 527.71 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.9840 (4), 12.6632 (6), 22.3163 (11) |
α, β, γ (°) | 91.574 (3), 94.154 (3), 103.791 (3) |
V (Å3) | 2183.11 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.40 |
Crystal size (mm) | 0.60 × 0.20 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART APEX II CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.489, 0.855 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 55655, 15712, 12030 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.111, 1.07 |
No. of reflections | 15712 |
No. of parameters | 595 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.67 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C9B—H9BA···O1Ai | 0.93 | 2.3496 | 3.261 (2) | 167 |
C21B—H21B···N1B | 0.93 | 2.5925 | 3.198 (3) | 123 |
C22A—H22A···O1Aii | 0.93 | 2.4194 | 3.199 (3) | 141 |
C25A—H25A···O2A | 0.93 | 2.5952 | 3.175 (3) | 121 |
C5B—H5BA···Cg3i | 0.93 | 3.0590 | 3.463 (3) | 108 |
C21A—H21A···Cg1 | 0.93 | 2.9697 | 3.397 (3) | 109 |
C21B—H21B···Cg2 | 0.93 | 2.8022 | 3.301 (2) | 115 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z. |
Schiff base ligands have played an important role in the development of coordination chemistry as they readily form stable complexes with most transition metal ions (Pal et al., 2005). It is also well known that zinc complexes with Schiff-bases are important in biological systems and coordination chemistry (Collinson & Fenton, 1996; Tarafder, Chew et al., 2002; Tarafder, Jin et al., 2002). Recently, we reported the crystal structure of aqua{2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(4-methoxyphenolato)- κ4O,O',N,N'}zinc(II), (II), derived from a related Schiff base ligand (Eltayeb et al., 2007). As an extension of our investigations of the structure of Schiff base zinc(II) complexes, the title mononuclear zinc(II) complex, (I) is reported here.
Complex (I) is a mononuclear zinc(II) compound (Fig. 1). There are two unique molecules in the asymmetric unit. Each ZnII ion is in a distorted square pyramidal geometry and five-coordinated by two N and two O atoms of a Schiff-base ligand forming the basal plane, and by the N atom of pyridine at the axial position. The bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable to the values in another closely related zinc(II) complex, (II) (Eltayeb et al., 2007). The bond angles around the central metal zinc(II) show some deviation from ideal square pyramidal geometry. The dihedral angles between the pyridine (C21–C25/N3) and C1–C6 or C15–C20 rings are 89.75 (11)° and 74.44 (10)°, respectively in molecule A [88.32 (10)Å and 75.71 (10)° in molecule B].
In the crystal structure of (I) as shown Fig. 2, adjacent molecules are linked through weak C—H···Cl interactions into chains running along the b axis. Between the adjacent chains, there are molecules which are arranged diagonally and are bridging these chains through weak C—H···O interactions. The crystal is stabilized by weak C—H···O intra- and intermolecular interactions (Table 1). C—H···π were also observed; Cg1, Cg2 and Cg3 are the centroids of Zn1A–O1A–C1A–C6A–C7A–N1A, Zn1B–O1B–C1B–C6B–C7B–N1B and C1A–C6A, respectively (Table 1).