The structure of the title complex, [Zn(C6H15NO3)2](C7H4NO3S)2, consists of a complex cation and two saccharinate (sac) anions. In the complex cation, the zinc(II) ion is octahedrally coordinated by two tridentate (N,O,O′) triethanolamine (tea) ligands with a facial distribution. Two ethanol groups of each tea ligand form two five-membered chelate rings around the zinc(II) ion, while the third ethanol group remains uncoordinated. In addition to weak π–π interactions between the phenyl rings of neighbouring sac ions, H atoms of free and coordinated hydroxyl groups are involved in hydrogen bonding with amine N, carbonyl O and sulfonyl O atoms of the adjacent sac ions, forming a three-dimensional network.
Supporting information
CCDC reference: 177189
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.113
- Data-to-parameter ratio = 19.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
ABSTY_01 Extra text has been found in the _exptl_absorpt_correction_type
field, which should be only a single keyword. A literature
citation should be included in the _exptl_absorpt_process_details
field.
HYDTR_01 Extra text has been found in the _refine_ls_hydrogen_treatment field.
Explanatory text should be in the _publ_section_refinement field.
Hydrogen treatment given as O-H freely, others riding
Hydrogen treatment identified as riding
Data collection: Bruker SMART (Bruker, 1998); cell refinement: Bruker SAINT (Bruker, 1998); data reduction: Bruker SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Siemens XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Bis(triethanolamine-N,
O,
O')zinc(II) saccharinate
top
Crystal data top
C12H30ZnN2O6·2(C7H4NO3S) | Z = 1 |
Mr = 728.09 | F(000) = 380 |
Triclinic, P1 | Dx = 1.647 Mg m−3 |
a = 7.9428 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.6647 (14) Å | Cell parameters from 8018 reflections |
c = 12.1383 (18) Å | θ = 2.6–30.5° |
α = 75.190 (6)° | µ = 1.05 mm−1 |
β = 87.432 (6)° | T = 133 K |
γ = 65.639 (6)° | Tablet, colourless |
V = 734.0 (2) Å3 | 0.34 × 0.15 × 0.08 mm |
Data collection top
Bruker SMART 1000 CCD diffractometer | 4266 independent reflections |
Radiation source: fine-focus sealed tube | 3731 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 8.192 pixels mm-1 | θmax = 30.0°, θmin = 1.7° |
ω– and phi–scans | h = −11→11 |
Absorption correction: multi-scans SADABS (Bruker, 1998) | k = −12→12 |
Tmin = 0.716, Tmax = 0.921 | l = −17→17 |
12918 measured reflections | |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | O-H freely, others riding |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0814P)2] where P = (Fo2 + 2Fc2)/3 |
4266 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 1.17 e Å−3 |
3 restraints | Δρmin = −1.81 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 | |
C11 | 0.2242 (2) | 0.1697 (2) | −0.00318 (14) | 0.0189 (3) | |
H11 | 0.3346 | 0.1207 | −0.0399 | 0.023* | |
C12 | 0.0551 (2) | 0.1831 (3) | −0.04192 (14) | 0.0217 (4) | |
H12 | 0.0501 | 0.1401 | −0.1057 | 0.026* | |
C13 | −0.1062 (2) | 0.2582 (3) | 0.01082 (15) | 0.0213 (4) | |
H13 | −0.2203 | 0.2684 | −0.0186 | 0.026* | |
C14 | −0.1036 (2) | 0.3187 (2) | 0.10590 (14) | 0.0173 (3) | |
H14 | −0.2140 | 0.3698 | 0.1421 | 0.021* | |
C15 | 0.0649 (2) | 0.3021 (2) | 0.14640 (13) | 0.0139 (3) | |
C16 | 0.2237 (2) | 0.2310 (2) | 0.09098 (13) | 0.0137 (3) | |
C21 | 0.1071 (2) | 0.3476 (2) | 0.24946 (13) | 0.0139 (3) | |
O21 | −0.01147 (16) | 0.41248 (18) | 0.31378 (10) | 0.0199 (3) | |
S1 | 0.40662 (5) | 0.23439 (5) | 0.16532 (3) | 0.01365 (10) | |
O1 | 0.47539 (17) | 0.35483 (19) | 0.09762 (12) | 0.0233 (3) | |
O2 | 0.54611 (16) | 0.05756 (17) | 0.21001 (11) | 0.0199 (3) | |
N1 | 0.28864 (18) | 0.3083 (2) | 0.26674 (12) | 0.0160 (3) | |
Zn | 0.5000 | 0.5000 | 0.5000 | 0.01210 (9) | |
N2 | 0.28036 (17) | 0.71296 (18) | 0.39446 (11) | 0.0125 (2) | |
C31 | 0.3139 (2) | 0.6954 (2) | 0.27609 (13) | 0.0159 (3) | |
H31A | 0.2324 | 0.8062 | 0.2215 | 0.019* | |
H31B | 0.2821 | 0.6007 | 0.2657 | 0.019* | |
C32 | 0.5136 (2) | 0.6540 (2) | 0.25049 (14) | 0.0177 (3) | |
H32A | 0.5372 | 0.6256 | 0.1757 | 0.021* | |
H32B | 0.5410 | 0.7565 | 0.2475 | 0.021* | |
O32 | 0.62860 (16) | 0.50652 (17) | 0.33969 (10) | 0.0174 (2) | |
H32 | 0.738 (3) | 0.472 (3) | 0.325 (2) | 0.031 (6)* | |
C33 | 0.1048 (2) | 0.6987 (2) | 0.43343 (14) | 0.0170 (3) | |
H33A | 0.0694 | 0.7484 | 0.5002 | 0.020* | |
H33B | 0.1309 | 0.5726 | 0.4601 | 0.020* | |
C34 | −0.0598 (2) | 0.7869 (2) | 0.34719 (15) | 0.0196 (3) | |
H34A | −0.0368 | 0.7234 | 0.2870 | 0.023* | |
H34B | −0.1710 | 0.7821 | 0.3853 | 0.023* | |
O34 | −0.09204 (17) | 0.96382 (18) | 0.29680 (12) | 0.0218 (3) | |
H34 | −0.192 (3) | 1.016 (4) | 0.262 (2) | 0.044 (8)* | |
C35 | 0.2832 (2) | 0.8797 (2) | 0.40519 (14) | 0.0164 (3) | |
H35A | 0.1551 | 0.9718 | 0.3959 | 0.020* | |
H35B | 0.3544 | 0.9195 | 0.3442 | 0.020* | |
C36 | 0.3705 (2) | 0.8524 (2) | 0.52025 (14) | 0.0179 (3) | |
H36A | 0.3800 | 0.9608 | 0.5255 | 0.021* | |
H36B | 0.2949 | 0.8217 | 0.5818 | 0.021* | |
O36 | 0.55215 (15) | 0.71114 (17) | 0.53114 (10) | 0.0160 (2) | |
H36 | 0.601 (3) | 0.714 (4) | 0.5844 (19) | 0.033 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C11 | 0.0181 (7) | 0.0249 (9) | 0.0122 (7) | −0.0068 (6) | 0.0018 (6) | −0.0060 (6) |
C12 | 0.0241 (8) | 0.0303 (10) | 0.0114 (7) | −0.0103 (7) | −0.0013 (6) | −0.0079 (7) |
C13 | 0.0183 (7) | 0.0294 (10) | 0.0167 (8) | −0.0100 (7) | −0.0027 (6) | −0.0061 (7) |
C14 | 0.0138 (7) | 0.0234 (9) | 0.0148 (7) | −0.0076 (6) | 0.0002 (5) | −0.0053 (6) |
C15 | 0.0141 (7) | 0.0178 (8) | 0.0086 (6) | −0.0064 (6) | −0.0004 (5) | −0.0018 (6) |
C16 | 0.0121 (6) | 0.0175 (8) | 0.0097 (6) | −0.0056 (6) | −0.0008 (5) | −0.0011 (6) |
C21 | 0.0154 (7) | 0.0168 (7) | 0.0105 (6) | −0.0077 (6) | 0.0006 (5) | −0.0035 (6) |
O21 | 0.0171 (5) | 0.0295 (7) | 0.0155 (6) | −0.0094 (5) | 0.0040 (4) | −0.0105 (5) |
S1 | 0.01049 (17) | 0.0175 (2) | 0.01146 (18) | −0.00541 (14) | 0.00005 (13) | −0.00193 (15) |
O1 | 0.0179 (6) | 0.0271 (7) | 0.0245 (6) | −0.0130 (5) | 0.0040 (5) | −0.0002 (5) |
O2 | 0.0147 (5) | 0.0191 (6) | 0.0193 (6) | −0.0022 (5) | −0.0033 (4) | −0.0018 (5) |
N1 | 0.0133 (6) | 0.0227 (7) | 0.0134 (6) | −0.0073 (5) | −0.0003 (5) | −0.0068 (6) |
Zn | 0.01152 (14) | 0.01488 (15) | 0.00689 (13) | −0.00357 (10) | −0.00090 (9) | −0.00087 (10) |
N2 | 0.0114 (5) | 0.0159 (6) | 0.0094 (6) | −0.0052 (5) | 0.0001 (4) | −0.0026 (5) |
C31 | 0.0157 (7) | 0.0206 (8) | 0.0084 (6) | −0.0055 (6) | −0.0006 (5) | −0.0019 (6) |
C32 | 0.0177 (7) | 0.0203 (8) | 0.0105 (7) | −0.0054 (6) | 0.0025 (5) | −0.0007 (6) |
O32 | 0.0130 (5) | 0.0226 (6) | 0.0103 (5) | −0.0044 (5) | 0.0010 (4) | 0.0011 (5) |
C33 | 0.0127 (7) | 0.0214 (8) | 0.0132 (7) | −0.0069 (6) | 0.0006 (5) | 0.0013 (6) |
C34 | 0.0148 (7) | 0.0219 (9) | 0.0190 (8) | −0.0070 (6) | −0.0019 (6) | −0.0009 (7) |
O34 | 0.0150 (6) | 0.0206 (7) | 0.0221 (6) | −0.0027 (5) | −0.0057 (5) | 0.0003 (5) |
C35 | 0.0182 (7) | 0.0152 (8) | 0.0142 (7) | −0.0059 (6) | −0.0016 (6) | −0.0023 (6) |
C36 | 0.0180 (7) | 0.0189 (8) | 0.0160 (7) | −0.0054 (6) | −0.0004 (6) | −0.0070 (6) |
O36 | 0.0145 (5) | 0.0213 (6) | 0.0115 (5) | −0.0063 (5) | −0.0025 (4) | −0.0043 (5) |
Geometric parameters (Å, º) top
C11—C16 | 1.377 (2) | C33—C34 | 1.510 (2) |
C11—C12 | 1.392 (2) | C34—O34 | 1.414 (2) |
C12—C13 | 1.388 (2) | C35—C36 | 1.507 (2) |
C13—C14 | 1.388 (2) | C36—O36 | 1.440 (2) |
C14—C15 | 1.385 (2) | C11—H11 | 0.9500 |
C15—C16 | 1.385 (2) | C12—H12 | 0.9500 |
C15—C21 | 1.494 (2) | C13—H13 | 0.9500 |
C16—S1 | 1.7585 (16) | C14—H14 | 0.9500 |
C21—O21 | 1.2385 (18) | C31—H31A | 0.9900 |
C21—N1 | 1.351 (2) | C31—H31B | 0.9900 |
S1—O1 | 1.4332 (13) | C32—H32A | 0.9900 |
S1—O2 | 1.4484 (13) | C32—H32B | 0.9900 |
S1—N1 | 1.6151 (14) | O32—H32 | 0.823 (18) |
Zn—N2i | 2.1037 (14) | C33—H33A | 0.9900 |
Zn—N2 | 2.1037 (14) | C33—H33B | 0.9900 |
Zn—O32 | 2.1555 (11) | C34—H34A | 0.9900 |
Zn—O32i | 2.1555 (11) | C34—H34B | 0.9900 |
Zn—O36i | 2.1573 (13) | O34—H34 | 0.807 (19) |
Zn—O36 | 2.1573 (13) | C35—H35A | 0.9900 |
N2—C31 | 1.4841 (19) | C35—H35B | 0.9900 |
N2—C35 | 1.492 (2) | C36—H36A | 0.9900 |
N2—C33 | 1.4953 (19) | C36—H36B | 0.9900 |
C31—C32 | 1.512 (2) | O36—H36 | 0.780 (19) |
C32—O32 | 1.434 (2) | | |
| | | |
C16—C11—C12 | 116.76 (15) | N2—C35—C36 | 110.31 (14) |
C13—C12—C11 | 121.28 (15) | O36—C36—C35 | 106.96 (12) |
C14—C13—C12 | 121.02 (15) | C36—O36—Zn | 103.81 (9) |
C15—C14—C13 | 117.96 (15) | C16—C11—H11 | 121.6 |
C14—C15—C16 | 120.24 (14) | C12—C11—H11 | 121.6 |
C14—C15—C21 | 128.61 (14) | C13—C12—H12 | 119.4 |
C16—C15—C21 | 111.13 (13) | C11—C12—H12 | 119.4 |
C11—C16—C15 | 122.70 (14) | C14—C13—H13 | 119.5 |
C11—C16—S1 | 130.25 (12) | C12—C13—H13 | 119.5 |
C15—C16—S1 | 107.04 (11) | C15—C14—H14 | 121.0 |
O21—C21—N1 | 123.14 (14) | C13—C14—H14 | 121.0 |
O21—C21—C15 | 123.64 (14) | N2—C31—H31A | 109.3 |
N1—C21—C15 | 113.21 (13) | C32—C31—H31A | 109.3 |
O1—S1—O2 | 114.74 (7) | N2—C31—H31B | 109.3 |
O1—S1—N1 | 111.69 (8) | C32—C31—H31B | 109.3 |
O2—S1—N1 | 110.57 (8) | H31A—C31—H31B | 108.0 |
O1—S1—C16 | 111.36 (8) | O32—C32—H32A | 110.1 |
O2—S1—C16 | 110.21 (8) | C31—C32—H32A | 110.1 |
N1—S1—C16 | 96.88 (7) | O32—C32—H32B | 110.1 |
C21—N1—S1 | 111.52 (11) | C31—C32—H32B | 110.1 |
N2i—Zn—N2 | 180.0 | H32A—C32—H32B | 108.4 |
N2i—Zn—O32 | 99.00 (5) | C32—O32—H32 | 111.1 (19) |
N2—Zn—O32 | 81.00 (5) | Zn—O32—H32 | 131.1 (19) |
N2i—Zn—O32i | 81.00 (5) | N2—C33—H33A | 108.1 |
N2—Zn—O32i | 99.00 (5) | C34—C33—H33A | 108.1 |
O32—Zn—O32i | 180.0 | N2—C33—H33B | 108.1 |
N2i—Zn—O36i | 81.21 (5) | C34—C33—H33B | 108.1 |
N2—Zn—O36i | 98.79 (5) | H33A—C33—H33B | 107.3 |
O32—Zn—O36i | 85.66 (5) | O34—C34—H34A | 109.5 |
O32i—Zn—O36i | 94.34 (5) | C33—C34—H34A | 109.5 |
N2i—Zn—O36 | 98.79 (5) | O34—C34—H34B | 109.5 |
N2—Zn—O36 | 81.21 (5) | C33—C34—H34B | 109.5 |
O32—Zn—O36 | 94.34 (5) | H34A—C34—H34B | 108.1 |
O32i—Zn—O36 | 85.66 (5) | C34—O34—H34 | 110 (2) |
O36i—Zn—O36 | 180.000 (1) | N2—C35—H35A | 109.6 |
C31—N2—C35 | 110.60 (13) | C36—C35—H35A | 109.6 |
C31—N2—C33 | 112.11 (12) | N2—C35—H35B | 109.6 |
C35—N2—C33 | 111.50 (12) | C36—C35—H35B | 109.6 |
C31—N2—Zn | 106.30 (9) | H35A—C35—H35B | 108.1 |
C35—N2—Zn | 108.84 (9) | O36—C36—H36A | 110.3 |
C33—N2—Zn | 107.24 (10) | C35—C36—H36A | 110.3 |
N2—C31—C32 | 111.50 (13) | O36—C36—H36B | 110.3 |
O32—C32—C31 | 107.90 (13) | C35—C36—H36B | 110.3 |
C32—O32—Zn | 111.67 (9) | H36A—C36—H36B | 108.6 |
N2—C33—C34 | 116.96 (13) | C36—O36—H36 | 104.5 (19) |
O34—C34—C33 | 110.78 (14) | Zn—O36—H36 | 129 (2) |
| | | |
C16—C11—C12—C13 | 1.3 (3) | O32—Zn—N2—C35 | −97.92 (10) |
C11—C12—C13—C14 | −1.6 (3) | O32i—Zn—N2—C35 | 82.08 (10) |
C12—C13—C14—C15 | 0.1 (3) | O36i—Zn—N2—C35 | 177.93 (9) |
C13—C14—C15—C16 | 1.5 (3) | O36—Zn—N2—C35 | −2.07 (9) |
C13—C14—C15—C21 | −176.60 (17) | O32—Zn—N2—C33 | 141.33 (11) |
C12—C11—C16—C15 | 0.4 (3) | O32i—Zn—N2—C33 | −38.67 (11) |
C12—C11—C16—S1 | 179.08 (14) | O36i—Zn—N2—C33 | 57.18 (10) |
C14—C15—C16—C11 | −1.8 (3) | O36—Zn—N2—C33 | −122.82 (10) |
C21—C15—C16—C11 | 176.61 (16) | C35—N2—C31—C32 | 72.46 (17) |
C14—C15—C16—S1 | 179.19 (14) | C33—N2—C31—C32 | −162.42 (14) |
C21—C15—C16—S1 | −2.36 (17) | Zn—N2—C31—C32 | −45.54 (16) |
C14—C15—C21—O21 | −1.4 (3) | N2—C31—C32—O32 | 51.47 (19) |
C16—C15—C21—O21 | −179.71 (17) | C31—C32—O32—Zn | −30.54 (16) |
C14—C15—C21—N1 | 177.61 (17) | N2i—Zn—O32—C32 | −174.54 (11) |
C16—C15—C21—N1 | −0.7 (2) | N2—Zn—O32—C32 | 5.46 (11) |
C11—C16—S1—O1 | 68.56 (19) | O36i—Zn—O32—C32 | 105.09 (11) |
C15—C16—S1—O1 | −112.57 (13) | O36—Zn—O32—C32 | −74.91 (11) |
C11—C16—S1—O2 | −59.96 (19) | C31—N2—C33—C34 | −39.9 (2) |
C15—C16—S1—O2 | 118.91 (12) | C35—N2—C33—C34 | 84.76 (18) |
C11—C16—S1—N1 | −174.90 (17) | Zn—N2—C33—C34 | −156.19 (13) |
C15—C16—S1—N1 | 3.97 (13) | N2—C33—C34—O34 | −51.7 (2) |
O21—C21—N1—S1 | −177.24 (14) | C31—N2—C35—C36 | −143.50 (13) |
C15—C21—N1—S1 | 3.72 (19) | C33—N2—C35—C36 | 91.03 (15) |
O1—S1—N1—C21 | 111.80 (13) | Zn—N2—C35—C36 | −27.07 (14) |
O2—S1—N1—C21 | −119.13 (13) | N2—C35—C36—O36 | 56.26 (16) |
C16—S1—N1—C21 | −4.49 (14) | C35—C36—O36—Zn | −54.34 (14) |
O32—Zn—N2—C31 | 21.23 (10) | N2i—Zn—O36—C36 | −148.73 (9) |
O32i—Zn—N2—C31 | −158.77 (10) | N2—Zn—O36—C36 | 31.27 (9) |
O36i—Zn—N2—C31 | −62.91 (10) | O32—Zn—O36—C36 | 111.46 (10) |
O36—Zn—N2—C31 | 117.09 (10) | O32i—Zn—O36—C36 | −68.54 (10) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O32—H32···O21ii | 0.82 (2) | 1.84 (2) | 2.6580 (16) | 170 (3) |
O34—H34···O2iii | 0.81 (2) | 2.06 (2) | 2.8174 (17) | 157 (3) |
O36—H36···N1i | 0.78 (2) | 1.97 (2) | 2.7453 (18) | 171 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y+1, z. |