Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049458/wm2151sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049458/wm2151Isup2.hkl |
CCDC reference: 667146
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.008 Å
- Disorder in main residue
- R factor = 0.068
- wR factor = 0.122
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.147 STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.449 From the CIF: _refine_ls_abs_structure_Flack_su 0.017 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT033_ALERT_2_C Flack Parameter Value Deviates 2 * su from zero. 0.45 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8 PLAT352_ALERT_3_C Short N-H Bond (0.87A) N4 - H4A ... 0.76 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C1 - C6 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C5 - C6 ... 1.37 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.54 From the CIF: _reflns_number_total 6894 Count of symmetry unique reflns 3969 Completeness (_total/calc) 173.70% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2925 Fraction of Friedel pairs measured 0.737 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of N4 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of N5 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 29
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 15 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 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For synthesis of [Zn(sac)2(H2O)4].2H2O used as an educt for crystal growth of the title compound, see: Koksal et al. (2001). For related structures containing sac ligands, see: Yeşilel et al., 2006; Yilmaz et al., 2002; 2006.
Under continous stirring at room temperature, an aqueous solution of paen (350 mg, 2.0 mmol) was added dropwise to 50 ml of an aqueous solution of [Zn(sac)2(H2O)4].2H2O (548 mg, 1.0 mmol). For synthesis of the latter compound, see: Koksal et al. (2001). The resulting solution was heated up to 353 K and stirred continuously for 4 h. Then the solution was allowed to cool to room temperature slowly. Small colourless crystals grown in the solution were filtered off and washed with cold distilled water and ethanol, and were finally dried.
The disordered sulfonyl group of the sacharinate ligand was modelled with two different orientations (S1A—S1B; O3A—O3B, O4A—O4B) and with refined occupancy factors of 0.383 (11) and 0.617 (11), respectively. All H atoms except those bonded to N4 and N5 atoms were placed in geometrically idealized positions with distances of d(N–H) = 0.90 Å; d(C–H) = 0.93 - 0.97 Å, and were refined as riding atoms with Uiso(H) = 1.2Ueq of the parent atoms. H atoms bonded to N4 and N5 were found from difference maps and were refined freely. H atoms of the water molecule were constrained to O—H distances of 0.85 (2) Å and were refined with Uiso(H) = 1.2Ueq(OW). The measured crystal was racemically twinned with an approximate twin ratio of 1:1.
In title compound the Zn(II) cation is octahedrally coordinated by two sac and one paen ligands. Most interestingly, the two sac ligands are bonded to the Zn site via the carbonyl O atoms although N-coordination is usually preferred by this ligand with first-row transition metals. The equatorial plane, defined by the atoms (N3, N4, N5, N6), of the octahedron is formed by N atoms of paen ligands, whereas the axial positions belong to the carbonyl O atoms of the sac ligands. The Zn—N bonds are slightly shorter than the Zn—O bonds (Table 1). Whereas the (O–Zn–O) angle is nearly linear, the trans- (N–Zn–N) angles of the equatorial plane deviate significantly from linearity. One of the sulfonyl groups of the sac ligands shows disorder, and was refined with two different orientations (see Fig. 1). However, the bond lengths and angles of the sac ligands are similiar to those observed in related structures (Yeşilel et al., 2006; Yilmaz et al., 2002; 2006).
The molecular packing is stabilized by intermolecular hydrogen bonds (Table2, Fig. 2). Neighbouring Zn(sac)2(paen) moieties are linked via water molecules through O—H···O and N—H···O hydrogen bonds, which leads to chains extending parallel to (010).
For synthesis of [Zn(sac)2(H2O)4].2H2O used as an educt for crystal growth of the title compound, see: Koksal et al. (2001). For related structures containing sac ligands, see: Yeşilel et al., 2006; Yilmaz et al., 2002; 2006.
Data collection: X-AREA (Stoe, 2002); cell refinement: X-AREA (Stoe, 2002); data reduction: X-RED32 (Stoe, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Zn(C7H4NO3S)2(C8H22N4)]·H2O | F(000) = 1296 |
Mr = 622.03 | Dx = 1.485 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 23038 reflections |
a = 10.1025 (5) Å | θ = 1.4–26.6° |
b = 14.3045 (10) Å | µ = 1.08 mm−1 |
c = 19.2547 (11) Å | T = 296 K |
V = 2782.5 (3) Å3 | Rectangular prism, colorless |
Z = 4 | 0.32 × 0.30 × 0.25 mm |
Stoe IPDSII diffractometer | 6894 independent reflections |
Radiation source: fine-focus sealed tube | 3763 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.148 |
ω scans | θmax = 28.5°, θmin = 1.8° |
Absorption correction: numerical (X-RED32; Stoe, 2002) | h = −12→13 |
Tmin = 0.710, Tmax = 0.811 | k = −19→18 |
49189 measured reflections | l = −25→25 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.068 | w = 1/[σ2(Fo2) + (0.0535P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.122 | (Δ/σ)max = 0.001 |
S = 0.92 | Δρmax = 0.37 e Å−3 |
6894 reflections | Δρmin = −0.36 e Å−3 |
381 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
29 restraints | Extinction coefficient: 0.0015 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 3014 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.449 (17) |
[Zn(C7H4NO3S)2(C8H22N4)]·H2O | V = 2782.5 (3) Å3 |
Mr = 622.03 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.1025 (5) Å | µ = 1.08 mm−1 |
b = 14.3045 (10) Å | T = 296 K |
c = 19.2547 (11) Å | 0.32 × 0.30 × 0.25 mm |
Stoe IPDSII diffractometer | 6894 independent reflections |
Absorption correction: numerical (X-RED32; Stoe, 2002) | 3763 reflections with I > 2σ(I) |
Tmin = 0.710, Tmax = 0.811 | Rint = 0.148 |
49189 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.122 | Δρmax = 0.37 e Å−3 |
S = 0.92 | Δρmin = −0.36 e Å−3 |
6894 reflections | Absolute structure: Flack (1983), 3014 Friedel pairs |
381 parameters | Absolute structure parameter: 0.449 (17) |
29 restraints |
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) | |
C1 | 0.1672 (4) | 0.4017 (3) | 0.1425 (2) | 0.0451 (10) | |
C2 | 0.1978 (5) | 0.3115 (3) | 0.1605 (3) | 0.0590 (13) | |
H2 | 0.2750 | 0.2830 | 0.1449 | 0.071* | |
C3 | 0.1087 (6) | 0.2641 (4) | 0.2031 (3) | 0.0728 (15) | |
H3 | 0.1278 | 0.2035 | 0.2175 | 0.087* | |
C4 | −0.0065 (6) | 0.3058 (4) | 0.2241 (3) | 0.0749 (15) | |
H4 | −0.0662 | 0.2717 | 0.2507 | 0.090* | |
C5 | −0.0361 (6) | 0.3954 (4) | 0.2072 (3) | 0.0755 (17) | |
H5 | −0.1127 | 0.4243 | 0.2232 | 0.091* | |
C6 | 0.0520 (5) | 0.4412 (4) | 0.1656 (3) | 0.0624 (14) | |
C7 | 0.2450 (5) | 0.4672 (3) | 0.0984 (3) | 0.0608 (13) | |
C8 | 0.8111 (4) | 0.6093 (3) | −0.1499 (2) | 0.0429 (10) | |
C9 | 0.7907 (5) | 0.7016 (3) | −0.1649 (3) | 0.0526 (12) | |
H9 | 0.7208 | 0.7345 | −0.1451 | 0.063* | |
C10 | 0.8768 (6) | 0.7441 (4) | −0.2101 (3) | 0.0694 (15) | |
H10 | 0.8649 | 0.8068 | −0.2212 | 0.083* | |
C11 | 0.9808 (7) | 0.6953 (4) | −0.2394 (3) | 0.0725 (16) | |
H11 | 1.0372 | 0.7255 | −0.2703 | 0.087* | |
C12 | 1.0022 (6) | 0.6024 (4) | −0.2234 (3) | 0.0682 (13) | |
H12 | 1.0724 | 0.5691 | −0.2424 | 0.082* | |
C13 | 0.9140 (4) | 0.5615 (3) | −0.1776 (2) | 0.0501 (11) | |
C14 | 0.7301 (4) | 0.5471 (3) | −0.1025 (2) | 0.0468 (10) | |
C15 | 0.4820 (6) | 0.2962 (3) | −0.0276 (3) | 0.0731 (15) | |
H15A | 0.4710 | 0.2454 | −0.0605 | 0.088* | |
H15B | 0.4096 | 0.2931 | 0.0054 | 0.088* | |
C16 | 0.6118 (6) | 0.2837 (4) | 0.0107 (3) | 0.0718 (15) | |
H16A | 0.6182 | 0.2191 | 0.0257 | 0.086* | |
H16B | 0.6837 | 0.2950 | −0.0216 | 0.086* | |
C17 | 0.6310 (6) | 0.3457 (4) | 0.0730 (3) | 0.0771 (17) | |
H17A | 0.5550 | 0.3393 | 0.1034 | 0.093* | |
H17B | 0.7083 | 0.3246 | 0.0985 | 0.093* | |
C18 | 0.3549 (6) | 0.3961 (4) | −0.1050 (4) | 0.0820 (17) | |
H18A | 0.2796 | 0.3785 | −0.0766 | 0.098* | |
H18B | 0.3576 | 0.3547 | −0.1449 | 0.098* | |
C19 | 0.3383 (6) | 0.4956 (4) | −0.1292 (3) | 0.0810 (16) | |
H19A | 0.4118 | 0.5128 | −0.1590 | 0.097* | |
H19B | 0.2572 | 0.5014 | −0.1559 | 0.097* | |
C20 | 0.3312 (6) | 0.6581 (4) | −0.0891 (3) | 0.0747 (16) | |
H20A | 0.2514 | 0.6705 | −0.1155 | 0.090* | |
H20B | 0.4065 | 0.6710 | −0.1188 | 0.090* | |
C21 | 0.3355 (6) | 0.7216 (4) | −0.0276 (4) | 0.084 (2) | |
H21A | 0.2642 | 0.7040 | 0.0035 | 0.101* | |
H21B | 0.3175 | 0.7847 | −0.0435 | 0.101* | |
C22 | 0.4633 (6) | 0.7233 (3) | 0.0139 (3) | 0.0760 (18) | |
H22A | 0.5375 | 0.7310 | −0.0176 | 0.091* | |
H22B | 0.4623 | 0.7765 | 0.0451 | 0.091* | |
N1 | 0.1887 (5) | 0.5510 (3) | 0.0913 (3) | 0.0946 (19) | |
N2 | 0.7764 (4) | 0.4591 (3) | −0.0980 (2) | 0.0628 (12) | |
N3 | 0.4813 (5) | 0.6373 (3) | 0.0542 (2) | 0.0702 (12) | |
H3A | 0.4140 | 0.6331 | 0.0847 | 0.084* | |
H3B | 0.5563 | 0.6432 | 0.0791 | 0.084* | |
N4 | 0.4754 (5) | 0.3859 (3) | −0.0651 (3) | 0.0616 (12) | |
N5 | 0.3334 (4) | 0.5583 (3) | −0.0687 (3) | 0.0658 (12) | |
N6 | 0.6482 (4) | 0.4462 (3) | 0.0551 (2) | 0.0693 (12) | |
H6A | 0.7227 | 0.4519 | 0.0298 | 0.083* | |
H6B | 0.6606 | 0.4782 | 0.0948 | 0.083* | |
O1 | 0.3520 (4) | 0.4442 (3) | 0.0723 (2) | 0.0758 (11) | |
O2 | 0.6306 (3) | 0.5774 (2) | −0.07302 (19) | 0.0600 (9) | |
O1W | 0.8016 (5) | 0.3978 (5) | −0.3387 (3) | 0.1273 (19) | |
O3A | 0.107 (2) | 0.6125 (9) | 0.2157 (8) | 0.101 (5) | 0.383 (11) |
O3B | 0.0292 (14) | 0.6268 (5) | 0.1665 (10) | 0.130 (6) | 0.617 (11) |
O4A | −0.0316 (15) | 0.5925 (16) | 0.1166 (15) | 0.115 (4) | 0.383 (11) |
O4B | −0.0713 (8) | 0.5555 (7) | 0.0682 (7) | 0.115 (4) | 0.617 (11) |
O5 | 0.8858 (5) | 0.3817 (3) | −0.1988 (2) | 0.1005 (16) | |
O6 | 1.0226 (4) | 0.4277 (3) | −0.1006 (2) | 0.1084 (17) | |
S1A | 0.0774 (9) | 0.5583 (5) | 0.1553 (5) | 0.079 (3) | 0.383 (11) |
S1B | 0.0367 (4) | 0.5542 (3) | 0.1183 (3) | 0.0725 (14) | 0.617 (11) |
S2 | 0.90760 (14) | 0.44672 (10) | −0.14354 (8) | 0.0665 (4) | |
Zn1 | 0.49146 (5) | 0.51064 (3) | −0.00068 (4) | 0.05359 (16) | |
H5A | 0.252 (6) | 0.548 (4) | −0.040 (3) | 0.082 (16)* | |
H4A | 0.548 (7) | 0.393 (5) | −0.073 (4) | 0.10 (3)* | |
H1W | 0.816 (7) | 0.405 (7) | −0.2951 (15) | 0.154* | |
H2W | 0.720 (2) | 0.405 (7) | −0.341 (4) | 0.154* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.049 (3) | 0.044 (2) | 0.042 (2) | −0.0024 (19) | 0.009 (2) | −0.0002 (19) |
C2 | 0.055 (3) | 0.062 (3) | 0.060 (3) | 0.005 (2) | 0.001 (3) | 0.008 (2) |
C3 | 0.077 (4) | 0.067 (3) | 0.075 (4) | −0.002 (3) | 0.004 (3) | 0.019 (3) |
C4 | 0.074 (4) | 0.082 (4) | 0.068 (3) | −0.021 (4) | 0.019 (3) | 0.007 (3) |
C5 | 0.072 (4) | 0.070 (3) | 0.084 (4) | −0.015 (3) | 0.038 (3) | −0.005 (3) |
C6 | 0.063 (3) | 0.057 (3) | 0.067 (3) | −0.003 (2) | 0.037 (3) | −0.001 (3) |
C7 | 0.053 (3) | 0.059 (3) | 0.070 (3) | −0.002 (2) | 0.022 (2) | 0.008 (3) |
C8 | 0.037 (2) | 0.047 (2) | 0.045 (3) | −0.0072 (19) | −0.0025 (19) | 0.001 (2) |
C9 | 0.061 (3) | 0.042 (2) | 0.054 (3) | −0.003 (2) | −0.002 (2) | 0.004 (2) |
C10 | 0.089 (4) | 0.052 (3) | 0.068 (4) | −0.014 (3) | −0.008 (3) | 0.016 (3) |
C11 | 0.084 (4) | 0.077 (3) | 0.056 (3) | −0.021 (3) | 0.018 (3) | 0.013 (2) |
C12 | 0.055 (3) | 0.081 (3) | 0.068 (3) | −0.003 (3) | 0.016 (3) | 0.007 (3) |
C13 | 0.047 (3) | 0.059 (3) | 0.045 (2) | 0.000 (2) | 0.015 (2) | 0.005 (2) |
C14 | 0.033 (2) | 0.055 (3) | 0.052 (3) | −0.003 (2) | 0.0064 (19) | 0.003 (2) |
C15 | 0.063 (4) | 0.058 (3) | 0.098 (4) | −0.002 (3) | 0.021 (3) | 0.010 (2) |
C16 | 0.069 (3) | 0.066 (3) | 0.080 (4) | 0.015 (2) | 0.012 (3) | 0.013 (3) |
C17 | 0.066 (4) | 0.085 (4) | 0.080 (4) | 0.020 (3) | 0.006 (3) | 0.030 (3) |
C18 | 0.074 (4) | 0.072 (4) | 0.100 (5) | −0.012 (3) | −0.013 (4) | 0.007 (3) |
C19 | 0.067 (3) | 0.087 (4) | 0.089 (4) | −0.004 (3) | −0.015 (3) | 0.011 (3) |
C20 | 0.061 (3) | 0.072 (4) | 0.091 (4) | 0.009 (3) | 0.004 (3) | 0.024 (3) |
C21 | 0.073 (4) | 0.059 (3) | 0.121 (6) | 0.016 (3) | 0.029 (4) | 0.030 (3) |
C22 | 0.080 (4) | 0.059 (3) | 0.089 (5) | 0.003 (2) | 0.033 (3) | −0.006 (3) |
N1 | 0.080 (3) | 0.049 (2) | 0.155 (5) | 0.007 (2) | 0.069 (3) | 0.022 (3) |
N2 | 0.053 (2) | 0.046 (2) | 0.090 (3) | 0.0027 (18) | 0.035 (2) | 0.016 (2) |
N3 | 0.069 (3) | 0.068 (2) | 0.074 (3) | 0.012 (2) | 0.020 (2) | 0.002 (2) |
N4 | 0.045 (3) | 0.053 (2) | 0.088 (3) | −0.0020 (19) | 0.010 (2) | 0.003 (2) |
N5 | 0.050 (2) | 0.063 (3) | 0.084 (3) | 0.005 (2) | 0.014 (2) | 0.022 (3) |
N6 | 0.061 (3) | 0.079 (3) | 0.068 (3) | 0.003 (2) | 0.009 (2) | 0.008 (2) |
O1 | 0.057 (2) | 0.075 (2) | 0.095 (3) | 0.008 (2) | 0.037 (2) | 0.021 (2) |
O2 | 0.0461 (19) | 0.059 (2) | 0.075 (2) | 0.0036 (15) | 0.0220 (17) | 0.0056 (17) |
O1W | 0.088 (4) | 0.187 (5) | 0.107 (4) | 0.000 (4) | −0.009 (3) | 0.013 (4) |
O3A | 0.120 (13) | 0.070 (8) | 0.113 (11) | 0.009 (8) | 0.033 (10) | 0.006 (8) |
O3B | 0.114 (9) | 0.048 (4) | 0.227 (15) | −0.009 (5) | 0.085 (9) | −0.047 (7) |
O4A | 0.050 (5) | 0.086 (6) | 0.209 (12) | 0.012 (4) | 0.004 (5) | 0.067 (7) |
O4B | 0.050 (5) | 0.086 (6) | 0.209 (12) | 0.012 (4) | 0.004 (5) | 0.067 (7) |
O5 | 0.140 (4) | 0.059 (2) | 0.103 (3) | −0.002 (3) | 0.048 (3) | −0.014 (2) |
O6 | 0.071 (3) | 0.136 (4) | 0.118 (4) | 0.045 (3) | 0.018 (3) | 0.063 (3) |
S1A | 0.087 (5) | 0.057 (3) | 0.095 (5) | 0.031 (3) | 0.059 (4) | 0.021 (4) |
S1B | 0.064 (2) | 0.0434 (13) | 0.110 (3) | 0.0058 (14) | 0.038 (2) | 0.008 (2) |
S2 | 0.0651 (8) | 0.0589 (7) | 0.0756 (9) | 0.0126 (6) | 0.0299 (7) | 0.0147 (7) |
Zn1 | 0.0456 (3) | 0.0536 (3) | 0.0616 (3) | 0.0076 (2) | 0.0124 (3) | 0.0074 (3) |
C1—C6 | 1.368 (6) | C18—C19 | 1.507 (7) |
C1—C2 | 1.372 (6) | C18—H18A | 0.9700 |
C1—C7 | 1.490 (6) | C18—H18B | 0.9700 |
C2—C3 | 1.393 (8) | C19—N5 | 1.471 (8) |
C2—H2 | 0.9300 | C19—H19A | 0.9700 |
C3—C4 | 1.369 (8) | C19—H19B | 0.9700 |
C3—H3 | 0.9300 | C20—N5 | 1.481 (6) |
C4—C5 | 1.356 (8) | C20—C21 | 1.492 (8) |
C4—H4 | 0.9300 | C20—H20A | 0.9700 |
C5—C6 | 1.364 (7) | C20—H20B | 0.9700 |
C5—H5 | 0.9300 | C21—C22 | 1.519 (8) |
C6—S1A | 1.706 (9) | C21—H21A | 0.9700 |
C6—S1B | 1.861 (7) | C21—H21B | 0.9700 |
C7—O1 | 1.237 (6) | C22—N3 | 1.466 (6) |
C7—N1 | 1.333 (6) | C22—H22A | 0.9700 |
C8—C13 | 1.355 (6) | C22—H22B | 0.9700 |
C8—C9 | 1.367 (6) | N1—S1B | 1.623 (6) |
C8—C14 | 1.514 (6) | N1—S1A | 1.671 (7) |
C9—C10 | 1.372 (7) | N2—S2 | 1.599 (4) |
C9—H9 | 0.9300 | N3—Zn1 | 2.100 (4) |
C10—C11 | 1.382 (8) | N3—H3A | 0.9000 |
C10—H10 | 0.9300 | N3—H3B | 0.9000 |
C11—C12 | 1.381 (8) | N4—Zn1 | 2.180 (5) |
C11—H11 | 0.9300 | N4—H4A | 0.76 (7) |
C12—C13 | 1.384 (6) | N5—Zn1 | 2.174 (5) |
C12—H12 | 0.9300 | N5—H5A | 1.00 (6) |
C13—S2 | 1.769 (5) | N6—Zn1 | 2.124 (4) |
C14—O2 | 1.233 (5) | N6—H6A | 0.9000 |
C14—N2 | 1.346 (6) | N6—H6B | 0.9000 |
C15—N4 | 1.473 (6) | O1—Zn1 | 2.204 (4) |
C15—C16 | 1.515 (8) | O2—Zn1 | 2.197 (3) |
C15—H15A | 0.9700 | O1W—H1W | 0.86 (2) |
C15—H15B | 0.9700 | O1W—H2W | 0.84 (2) |
C16—C17 | 1.505 (8) | O3A—S1A | 1.430 (14) |
C16—H16A | 0.9700 | O3B—S1B | 1.395 (11) |
C16—H16B | 0.9700 | O4A—S1A | 1.417 (14) |
C17—N6 | 1.489 (7) | O4B—S1B | 1.456 (11) |
C17—H17A | 0.9700 | O5—S2 | 1.431 (5) |
C17—H17B | 0.9700 | O6—S2 | 1.452 (4) |
C18—N4 | 1.446 (7) | ||
C6—C1—C2 | 119.9 (4) | C21—C20—H20B | 109.2 |
C6—C1—C7 | 112.0 (4) | H20A—C20—H20B | 107.9 |
C2—C1—C7 | 128.1 (4) | C20—C21—C22 | 116.8 (5) |
C1—C2—C3 | 117.4 (5) | C20—C21—H21A | 108.1 |
C1—C2—H2 | 121.3 | C22—C21—H21A | 108.1 |
C3—C2—H2 | 121.3 | C20—C21—H21B | 108.1 |
C4—C3—C2 | 120.8 (5) | C22—C21—H21B | 108.1 |
C4—C3—H3 | 119.6 | H21A—C21—H21B | 107.3 |
C2—C3—H3 | 119.6 | N3—C22—C21 | 111.7 (4) |
C5—C4—C3 | 121.9 (5) | N3—C22—H22A | 109.3 |
C5—C4—H4 | 119.1 | C21—C22—H22A | 109.3 |
C3—C4—H4 | 119.1 | N3—C22—H22B | 109.3 |
C4—C5—C6 | 116.8 (5) | C21—C22—H22B | 109.3 |
C4—C5—H5 | 121.6 | H22A—C22—H22B | 107.9 |
C6—C5—H5 | 121.6 | C7—N1—S1B | 113.3 (4) |
C5—C6—C1 | 123.2 (5) | C7—N1—S1A | 105.5 (4) |
C5—C6—S1A | 129.6 (4) | C14—N2—S2 | 110.9 (3) |
C1—C6—S1A | 103.9 (4) | C22—N3—Zn1 | 117.6 (3) |
C5—C6—S1B | 130.5 (4) | C22—N3—H3A | 107.9 |
C1—C6—S1B | 105.7 (4) | Zn1—N3—H3A | 107.9 |
O1—C7—N1 | 124.8 (4) | C22—N3—H3B | 107.9 |
O1—C7—C1 | 121.7 (4) | Zn1—N3—H3B | 107.9 |
N1—C7—C1 | 113.5 (4) | H3A—N3—H3B | 107.2 |
C13—C8—C9 | 121.4 (4) | C18—N4—C15 | 112.7 (4) |
C13—C8—C14 | 110.8 (4) | C18—N4—Zn1 | 106.4 (3) |
C9—C8—C14 | 127.8 (4) | C15—N4—Zn1 | 115.5 (4) |
C8—C9—C10 | 117.8 (5) | C18—N4—H4A | 134 (6) |
C8—C9—H9 | 121.1 | C15—N4—H4A | 100 (5) |
C10—C9—H9 | 121.1 | Zn1—N4—H4A | 86 (5) |
C9—C10—C11 | 121.2 (5) | C19—N5—C20 | 112.2 (5) |
C9—C10—H10 | 119.4 | C19—N5—Zn1 | 105.2 (3) |
C11—C10—H10 | 119.4 | C20—N5—Zn1 | 118.2 (4) |
C12—C11—C10 | 120.9 (5) | C19—N5—H5A | 112 (3) |
C12—C11—H11 | 119.5 | C20—N5—H5A | 106 (3) |
C10—C11—H11 | 119.5 | Zn1—N5—H5A | 103 (3) |
C11—C12—C13 | 116.6 (5) | C17—N6—Zn1 | 116.7 (4) |
C11—C12—H12 | 121.7 | C17—N6—H6A | 108.1 |
C13—C12—H12 | 121.7 | Zn1—N6—H6A | 108.1 |
C8—C13—C12 | 122.1 (5) | C17—N6—H6B | 108.1 |
C8—C13—S2 | 107.1 (3) | Zn1—N6—H6B | 108.1 |
C12—C13—S2 | 130.7 (4) | H6A—N6—H6B | 107.3 |
O2—C14—N2 | 125.6 (4) | C7—O1—Zn1 | 134.7 (3) |
O2—C14—C8 | 120.8 (4) | C14—O2—Zn1 | 131.4 (3) |
N2—C14—C8 | 113.7 (4) | H1W—O1W—H2W | 102 (7) |
N4—C15—C16 | 112.4 (4) | O4A—S1A—O3A | 113.8 (13) |
N4—C15—H15A | 109.1 | O4A—S1A—N1 | 99.0 (11) |
C16—C15—H15A | 109.1 | O3A—S1A—N1 | 119.6 (9) |
N4—C15—H15B | 109.1 | O4A—S1A—C6 | 106.5 (10) |
C16—C15—H15B | 109.1 | O3A—S1A—C6 | 117.9 (7) |
H15A—C15—H15B | 107.9 | N1—S1A—C6 | 97.2 (4) |
C17—C16—C15 | 115.5 (5) | O3B—S1B—O4B | 113.0 (8) |
C17—C16—H16A | 108.4 | O3B—S1B—N1 | 106.6 (6) |
C15—C16—H16A | 108.4 | O4B—S1B—N1 | 119.8 (5) |
C17—C16—H16B | 108.4 | O3B—S1B—C6 | 109.0 (7) |
C15—C16—H16B | 108.4 | O4B—S1B—C6 | 113.4 (4) |
H16A—C16—H16B | 107.5 | N1—S1B—C6 | 93.1 (3) |
N6—C17—C16 | 113.5 (5) | O5—S2—O6 | 115.1 (3) |
N6—C17—H17A | 108.9 | O5—S2—N2 | 110.7 (3) |
C16—C17—H17A | 108.9 | O6—S2—N2 | 111.8 (2) |
N6—C17—H17B | 108.9 | O5—S2—C13 | 109.5 (2) |
C16—C17—H17B | 108.9 | O6—S2—C13 | 110.9 (3) |
H17A—C17—H17B | 107.7 | N2—S2—C13 | 97.5 (2) |
N4—C18—C19 | 110.7 (5) | N3—Zn1—N6 | 99.03 (19) |
N4—C18—H18A | 109.5 | N3—Zn1—N5 | 89.83 (19) |
C19—C18—H18A | 109.5 | N6—Zn1—N5 | 171.1 (2) |
N4—C18—H18B | 109.5 | N3—Zn1—N4 | 171.58 (18) |
C19—C18—H18B | 109.5 | N6—Zn1—N4 | 89.30 (18) |
H18A—C18—H18B | 108.1 | N5—Zn1—N4 | 81.88 (19) |
N5—C19—C18 | 109.5 (5) | N3—Zn1—O2 | 88.58 (15) |
N5—C19—H19A | 109.8 | N6—Zn1—O2 | 91.83 (16) |
C18—C19—H19A | 109.8 | N5—Zn1—O2 | 87.23 (15) |
N5—C19—H19B | 109.8 | N4—Zn1—O2 | 92.45 (16) |
C18—C19—H19B | 109.8 | N3—Zn1—O1 | 91.14 (17) |
H19A—C19—H19B | 108.2 | N6—Zn1—O1 | 88.13 (15) |
N5—C20—C21 | 112.1 (5) | N5—Zn1—O1 | 92.84 (17) |
N5—C20—H20A | 109.2 | N4—Zn1—O1 | 87.83 (17) |
C21—C20—H20A | 109.2 | O2—Zn1—O1 | 179.72 (18) |
N5—C20—H20B | 109.2 | ||
C6—C1—C2—C3 | −0.8 (8) | C1—C6—S1A—O4A | 127.3 (13) |
C7—C1—C2—C3 | 179.6 (5) | S1B—C6—S1A—O4A | 29.9 (12) |
C1—C2—C3—C4 | 2.0 (9) | C5—C6—S1A—O3A | 56.1 (12) |
C2—C3—C4—C5 | −3.0 (10) | C1—C6—S1A—O3A | −103.4 (10) |
C3—C4—C5—C6 | 2.7 (10) | S1B—C6—S1A—O3A | 159.2 (13) |
C4—C5—C6—C1 | −1.6 (9) | C5—C6—S1A—N1 | −174.9 (6) |
C4—C5—C6—S1A | −157.6 (7) | C1—C6—S1A—N1 | 25.7 (7) |
C4—C5—C6—S1B | 168.0 (5) | S1B—C6—S1A—N1 | −71.8 (6) |
C2—C1—C6—C5 | 0.7 (9) | C7—N1—S1B—O3B | 125.5 (9) |
C7—C1—C6—C5 | −179.6 (5) | S1A—N1—S1B—O3B | 45.7 (10) |
C2—C1—C6—S1A | 161.8 (6) | C7—N1—S1B—O4B | −104.7 (7) |
C7—C1—C6—S1A | −18.5 (7) | S1A—N1—S1B—O4B | 175.6 (10) |
C2—C1—C6—S1B | −171.1 (5) | C7—N1—S1B—C6 | 14.6 (6) |
C7—C1—C6—S1B | 8.6 (6) | S1A—N1—S1B—C6 | −65.1 (7) |
C6—C1—C7—O1 | −179.7 (5) | C5—C6—S1B—O3B | 67.1 (9) |
C2—C1—C7—O1 | 0.0 (9) | C1—C6—S1B—O3B | −122.0 (7) |
C6—C1—C7—N1 | 1.1 (7) | S1A—C6—S1B—O3B | −32.4 (8) |
C2—C1—C7—N1 | −179.3 (6) | C5—C6—S1B—O4B | −59.8 (8) |
C13—C8—C9—C10 | 1.1 (7) | C1—C6—S1B—O4B | 111.2 (6) |
C14—C8—C9—C10 | −179.4 (4) | S1A—C6—S1B—O4B | −159.2 (9) |
C8—C9—C10—C11 | −0.1 (8) | C5—C6—S1B—N1 | 175.8 (6) |
C9—C10—C11—C12 | −0.7 (9) | C1—C6—S1B—N1 | −13.3 (5) |
C10—C11—C12—C13 | 0.6 (8) | S1A—C6—S1B—N1 | 76.4 (6) |
C9—C8—C13—C12 | −1.2 (7) | C14—N2—S2—O5 | −115.8 (4) |
C14—C8—C13—C12 | 179.2 (4) | C14—N2—S2—O6 | 114.4 (4) |
C9—C8—C13—S2 | 178.4 (4) | C14—N2—S2—C13 | −1.7 (4) |
C14—C8—C13—S2 | −1.2 (5) | C8—C13—S2—O5 | 116.8 (4) |
C11—C12—C13—C8 | 0.3 (8) | C12—C13—S2—O5 | −63.7 (6) |
C11—C12—C13—S2 | −179.2 (4) | C8—C13—S2—O6 | −115.1 (4) |
C13—C8—C14—O2 | −178.9 (5) | C12—C13—S2—O6 | 64.4 (6) |
C9—C8—C14—O2 | 1.6 (7) | C8—C13—S2—N2 | 1.7 (4) |
C13—C8—C14—N2 | 0.1 (6) | C12—C13—S2—N2 | −178.8 (5) |
C9—C8—C14—N2 | −179.4 (5) | C22—N3—Zn1—N6 | 138.1 (4) |
N4—C15—C16—C17 | 70.4 (6) | C22—N3—Zn1—N5 | −40.7 (4) |
C15—C16—C17—N6 | −68.9 (6) | C22—N3—Zn1—O2 | 46.5 (4) |
N4—C18—C19—N5 | −59.4 (7) | C22—N3—Zn1—O1 | −133.6 (4) |
N5—C20—C21—C22 | 68.2 (7) | C17—N6—Zn1—N3 | 136.5 (4) |
C20—C21—C22—N3 | −72.1 (6) | C17—N6—Zn1—N4 | −42.2 (4) |
O1—C7—N1—S1B | 168.7 (5) | C17—N6—Zn1—O2 | −134.6 (4) |
C1—C7—N1—S1B | −12.1 (8) | C17—N6—Zn1—O1 | 45.6 (4) |
O1—C7—N1—S1A | −161.8 (7) | C19—N5—Zn1—N3 | 163.8 (3) |
C1—C7—N1—S1A | 17.4 (8) | C20—N5—Zn1—N3 | 37.6 (4) |
O2—C14—N2—S2 | −179.9 (4) | C19—N5—Zn1—N4 | −17.7 (3) |
C8—C14—N2—S2 | 1.2 (5) | C20—N5—Zn1—N4 | −143.8 (5) |
C21—C22—N3—Zn1 | 60.2 (6) | C19—N5—Zn1—O2 | 75.2 (3) |
C19—C18—N4—C15 | 167.5 (5) | C20—N5—Zn1—O2 | −51.0 (4) |
C19—C18—N4—Zn1 | 40.0 (6) | C19—N5—Zn1—O1 | −105.1 (3) |
C16—C15—N4—C18 | 176.7 (5) | C20—N5—Zn1—O1 | 128.8 (4) |
C16—C15—N4—Zn1 | −60.7 (5) | C18—N4—Zn1—N6 | 169.4 (4) |
C18—C19—N5—C20 | 174.1 (5) | C15—N4—Zn1—N6 | 43.5 (4) |
C18—C19—N5—Zn1 | 44.3 (5) | C18—N4—Zn1—N5 | −11.9 (4) |
C21—C20—N5—C19 | −176.1 (5) | C15—N4—Zn1—N5 | −137.8 (4) |
C21—C20—N5—Zn1 | −53.4 (6) | C18—N4—Zn1—O2 | −98.8 (4) |
C16—C17—N6—Zn1 | 58.9 (6) | C15—N4—Zn1—O2 | 135.3 (4) |
N1—C7—O1—Zn1 | −6.3 (10) | C18—N4—Zn1—O1 | 81.3 (4) |
C1—C7—O1—Zn1 | 174.6 (4) | C15—N4—Zn1—O1 | −44.6 (4) |
N2—C14—O2—Zn1 | 2.1 (8) | C14—O2—Zn1—N3 | 142.0 (5) |
C8—C14—O2—Zn1 | −179.1 (3) | C14—O2—Zn1—N6 | 43.0 (4) |
C7—N1—S1A—O4A | −133.4 (12) | C14—O2—Zn1—N5 | −128.1 (5) |
S1B—N1—S1A—O4A | −23.0 (11) | C14—O2—Zn1—N4 | −46.4 (5) |
C7—N1—S1A—O3A | 102.6 (9) | C7—O1—Zn1—N3 | 46.4 (6) |
S1B—N1—S1A—O3A | −147.1 (12) | C7—O1—Zn1—N6 | 145.4 (6) |
C7—N1—S1A—C6 | −25.4 (8) | C7—O1—Zn1—N5 | −43.5 (6) |
S1B—N1—S1A—C6 | 85.0 (9) | C7—O1—Zn1—N4 | −125.3 (6) |
C5—C6—S1A—O4A | −73.2 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N1 | 0.90 | 2.56 | 3.282 (7) | 137 |
N6—H6A···N2 | 0.90 | 2.52 | 3.224 (6) | 135 |
N5—H5A···N1 | 1.00 (6) | 2.60 (6) | 3.411 (7) | 138 (4) |
N4—H4A···N2 | 0.76 (7) | 2.53 (7) | 3.278 (6) | 166 (7) |
O1W—H1W···O5 | 0.86 (2) | 2.01 (3) | 2.833 (8) | 161 (8) |
N3—H3B···O1Wi | 0.90 | 2.22 | 3.052 (7) | 154 |
N6—H6B···O1Wi | 0.90 | 2.22 | 3.071 (9) | 157 |
Symmetry code: (i) −x+3/2, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C7H4NO3S)2(C8H22N4)]·H2O |
Mr | 622.03 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 10.1025 (5), 14.3045 (10), 19.2547 (11) |
V (Å3) | 2782.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.08 |
Crystal size (mm) | 0.32 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Numerical (X-RED32; Stoe, 2002) |
Tmin, Tmax | 0.710, 0.811 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 49189, 6894, 3763 |
Rint | 0.148 |
(sin θ/λ)max (Å−1) | 0.672 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.122, 0.92 |
No. of reflections | 6894 |
No. of parameters | 381 |
No. of restraints | 29 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.37, −0.36 |
Absolute structure | Flack (1983), 3014 Friedel pairs |
Absolute structure parameter | 0.449 (17) |
Computer programs: X-AREA (Stoe, 2002), X-RED32 (Stoe, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).
N3—Zn1 | 2.100 (4) | N6—Zn1 | 2.124 (4) |
N4—Zn1 | 2.180 (5) | O1—Zn1 | 2.204 (4) |
N5—Zn1 | 2.174 (5) | O2—Zn1 | 2.197 (3) |
N6—Zn1—N5 | 171.1 (2) | O2—Zn1—O1 | 179.72 (18) |
N3—Zn1—N4 | 171.58 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N1 | 0.90 | 2.56 | 3.282 (7) | 137.2 |
N6—H6A···N2 | 0.90 | 2.52 | 3.224 (6) | 135.3 |
N5—H5A···N1 | 1.00 (6) | 2.60 (6) | 3.411 (7) | 138 (4) |
N4—H4A···N2 | 0.76 (7) | 2.53 (7) | 3.278 (6) | 166 (7) |
O1W—H1W···O5 | 0.86 (2) | 2.01 (3) | 2.833 (8) | 161 (8) |
N3—H3B···O1Wi | 0.90 | 2.22 | 3.052 (7) | 154.2 |
N6—H6B···O1Wi | 0.90 | 2.22 | 3.071 (9) | 157.0 |
Symmetry code: (i) −x+3/2, −y+1, z+1/2. |
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In title compound the Zn(II) cation is octahedrally coordinated by two sac and one paen ligands. Most interestingly, the two sac ligands are bonded to the Zn site via the carbonyl O atoms although N-coordination is usually preferred by this ligand with first-row transition metals. The equatorial plane, defined by the atoms (N3, N4, N5, N6), of the octahedron is formed by N atoms of paen ligands, whereas the axial positions belong to the carbonyl O atoms of the sac ligands. The Zn—N bonds are slightly shorter than the Zn—O bonds (Table 1). Whereas the (O–Zn–O) angle is nearly linear, the trans- (N–Zn–N) angles of the equatorial plane deviate significantly from linearity. One of the sulfonyl groups of the sac ligands shows disorder, and was refined with two different orientations (see Fig. 1). However, the bond lengths and angles of the sac ligands are similiar to those observed in related structures (Yeşilel et al., 2006; Yilmaz et al., 2002; 2006).
The molecular packing is stabilized by intermolecular hydrogen bonds (Table2, Fig. 2). Neighbouring Zn(sac)2(paen) moieties are linked via water molecules through O—H···O and N—H···O hydrogen bonds, which leads to chains extending parallel to (010).