The crystal structure of the title compound, [Zn(C6H4NO2)(C6H6N4S2)(H2O)3]2(C6H4NO2)2·[Zn(C6H4NO2)2(C6H6N4S2)(H2O)2]·4H2O, consists of four discrete components. In the neutral complex the Zn ion is located on a crystallographic twofold axis. The two thiazole rings of the diaminobithiazole ligand are twisted with respect to each other [dihedral angle = 13.85 (9)°] in the neutral complex but are coplanar [dihedral angle = 3.54 (15)°] in the cationic complex. π–π stacking is observed between nearly parallel pyridine rings.
Supporting information
CCDC reference: 618119
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- H-atom completeness 94%
- Disorder in solvent or counterion
- R factor = 0.038
- wR factor = 0.098
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact N51 .. O2WB .. 2.85 Ang.
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 8.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O2WA
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... <O2WB
PLAT322_ALERT_2_C Check Hybridisation of S31 in Main Residue . ?
PLAT322_ALERT_2_C Check Hybridisation of S11 in Main Residue . ?
PLAT322_ALERT_2_C Check Hybridisation of S12 in Main Residue . ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C54 H66 N18 O24 S6 Zn3
Atom count from the _atom_site data: C54 H62 N18 O24 S6 Zn3
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C54 H66 N18 O24 S6 Zn3
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 216.00 216.00 0.00
H 264.00 248.00 16.00
N 72.00 72.00 0.00
O 96.00 96.00 0.00
S 24.00 24.00 0.00
Zn 12.00 12.00 0.00
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
5 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
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Bis[triaqua(2,2'-diamino-4,4'-bi-1,3-thiazole)isonicotinatozinc(II)]
bis(isonicotinate)
diaqua(2,2'-diamino-4,4'-bi-1,3-thiazole)bis(isonicotinato)zinc(II)
tetrahydrate
top
Crystal data top
[Zn(C6H4NO2)(C6H6N4S2)(H2O)3]2(C6H4NO2)2.
[Zn(C6H4NO2)2(C6H6N4S2)(H2O)2]·4H2O | F(000) = 3576 |
Mr = 1739.72 | Dx = 1.632 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4950 reflections |
a = 36.196 (3) Å | θ = 2.8–25.0° |
b = 10.1184 (9) Å | µ = 1.28 mm−1 |
c = 20.4410 (17) Å | T = 295 K |
β = 108.967 (12)° | Prism, yellow |
V = 7079.9 (11) Å3 | 0.34 × 0.25 × 0.20 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 6224 independent reflections |
Radiation source: fine-focus sealed tube | 5136 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 10.0 pixels mm-1 | θmax = 25.0°, θmin = 1.2° |
ω scans | h = −42→40 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −11→12 |
Tmin = 0.680, Tmax = 0.780 | l = −24→23 |
17955 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.048P)2 + 6.9519P] where P = (Fo2 + 2Fc2)/3 |
6224 reflections | (Δ/σ)max = 0.003 |
484 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.33 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 | Occ. (<1) |
Zn1 | 0.694629 (9) | 0.55606 (3) | 0.559557 (16) | 0.02846 (11) | |
Zn2 | 0.5000 | 0.92746 (4) | 0.7500 | 0.02544 (12) | |
O1 | 0.74026 (6) | 0.5896 (2) | 0.51133 (10) | 0.0410 (5) | |
H1A | 0.7635 | 0.6042 | 0.5290 | 0.062* | |
H1B | 0.7318 | 0.6200 | 0.4706 | 0.062* | |
O2 | 0.72163 (5) | 0.70164 (19) | 0.63457 (9) | 0.0361 (5) | |
H2A | 0.7417 | 0.7437 | 0.6334 | 0.054* | |
H2B | 0.7066 | 0.7511 | 0.6470 | 0.054* | |
O3 | 0.66121 (5) | 0.70455 (18) | 0.49344 (9) | 0.0358 (5) | |
H3A | 0.6709 | 0.7516 | 0.4710 | 0.054* | |
H3B | 0.6507 | 0.7635 | 0.5107 | 0.054* | |
O4 | 0.47029 (5) | 0.77539 (18) | 0.67936 (9) | 0.0315 (4) | |
H4A | 0.4548 | 0.7256 | 0.6921 | 0.047* | |
H4B | 0.4904 | 0.7218 | 0.6756 | 0.047* | |
O21 | 0.52706 (6) | 0.6057 (2) | 0.66863 (10) | 0.0424 (5) | |
O22 | 0.57349 (6) | 0.6133 (2) | 0.77088 (9) | 0.0395 (5) | |
O41 | 0.62687 (6) | 0.8831 (2) | 0.54772 (10) | 0.0414 (5) | |
O42 | 0.67118 (6) | 0.8770 (2) | 0.65309 (10) | 0.0402 (5) | |
O51 | 0.78603 (6) | 0.8323 (3) | 0.63083 (12) | 0.0577 (6) | |
O52 | 0.81603 (7) | 0.6631 (2) | 0.60081 (11) | 0.0565 (6) | |
N11 | 0.67371 (6) | 0.4001 (2) | 0.48927 (11) | 0.0313 (5) | |
N12 | 0.62471 (8) | 0.4895 (3) | 0.39448 (13) | 0.0511 (7) | |
H12A | 0.6269 | 0.5606 | 0.4152 | 0.077* | |
H12B | 0.6093 | 0.4771 | 0.3548 | 0.077* | |
N13 | 0.72907 (6) | 0.3953 (2) | 0.61540 (11) | 0.0297 (5) | |
N14 | 0.76902 (8) | 0.4763 (3) | 0.72253 (13) | 0.0498 (7) | |
H14A | 0.7594 | 0.5550 | 0.7118 | 0.075* | |
H14B | 0.7873 | 0.4557 | 0.7567 | 0.075* | |
N21 | 0.64960 (6) | 0.5463 (2) | 0.60789 (11) | 0.0290 (5) | |
N31 | 0.47219 (6) | 1.0903 (2) | 0.68552 (11) | 0.0279 (5) | |
N32 | 0.42959 (7) | 1.0059 (3) | 0.58121 (12) | 0.0450 (7) | |
H32A | 0.4354 | 0.9289 | 0.5958 | 0.067* | |
H32B | 0.4151 | 1.0180 | 0.5407 | 0.067* | |
N41 | 0.54493 (6) | 0.9253 (2) | 0.70158 (11) | 0.0285 (5) | |
N51 | 0.89533 (10) | 0.7355 (3) | 0.84941 (15) | 0.0585 (8) | |
S11 | 0.64243 (3) | 0.23215 (9) | 0.39370 (5) | 0.0572 (3) | |
S12 | 0.77721 (3) | 0.22485 (9) | 0.68819 (5) | 0.0569 (3) | |
S31 | 0.44383 (3) | 1.26650 (8) | 0.59227 (4) | 0.0480 (2) | |
C13 | 0.64684 (8) | 0.3901 (3) | 0.42814 (14) | 0.0351 (7) | |
C12 | 0.67907 (11) | 0.1796 (3) | 0.46588 (18) | 0.0581 (10) | |
H12 | 0.6886 | 0.0936 | 0.4731 | 0.070* | |
C11 | 0.69199 (9) | 0.2792 (3) | 0.51021 (15) | 0.0377 (7) | |
C14 | 0.72283 (9) | 0.2783 (3) | 0.57779 (15) | 0.0375 (7) | |
C15 | 0.74611 (11) | 0.1775 (3) | 0.60848 (18) | 0.0570 (9) | |
H15 | 0.7455 | 0.0938 | 0.5894 | 0.068* | |
C16 | 0.75702 (8) | 0.3816 (3) | 0.67502 (15) | 0.0360 (7) | |
C21 | 0.61128 (8) | 0.5520 (3) | 0.57120 (15) | 0.0344 (7) | |
H21 | 0.6038 | 0.5460 | 0.5233 | 0.041* | |
C22 | 0.58279 (8) | 0.5663 (3) | 0.60116 (14) | 0.0332 (6) | |
H22 | 0.5567 | 0.5713 | 0.5735 | 0.040* | |
C23 | 0.59246 (8) | 0.5736 (2) | 0.67238 (14) | 0.0275 (6) | |
C24 | 0.63171 (8) | 0.5632 (3) | 0.71051 (14) | 0.0304 (6) | |
H24 | 0.6397 | 0.5660 | 0.7586 | 0.036* | |
C25 | 0.65884 (8) | 0.5487 (3) | 0.67688 (14) | 0.0313 (6) | |
H25 | 0.6850 | 0.5402 | 0.7035 | 0.038* | |
C26 | 0.56185 (8) | 0.5985 (3) | 0.70691 (14) | 0.0294 (6) | |
C33 | 0.44850 (8) | 1.1046 (3) | 0.62154 (14) | 0.0312 (6) | |
C32 | 0.47488 (9) | 1.3167 (3) | 0.67159 (16) | 0.0463 (8) | |
H32 | 0.4823 | 1.4037 | 0.6835 | 0.056* | |
C31 | 0.48687 (8) | 1.2117 (3) | 0.71405 (14) | 0.0305 (6) | |
C41 | 0.58257 (8) | 0.9250 (3) | 0.74065 (14) | 0.0305 (6) | |
H41 | 0.5886 | 0.9316 | 0.7884 | 0.037* | |
C42 | 0.61289 (8) | 0.9155 (3) | 0.71421 (14) | 0.0303 (6) | |
H42 | 0.6386 | 0.9140 | 0.7437 | 0.036* | |
C43 | 0.60476 (8) | 0.9084 (2) | 0.64351 (13) | 0.0267 (6) | |
C44 | 0.56592 (8) | 0.9125 (3) | 0.60251 (14) | 0.0348 (7) | |
H44 | 0.5592 | 0.9100 | 0.5546 | 0.042* | |
C45 | 0.53729 (8) | 0.9204 (3) | 0.63315 (14) | 0.0352 (7) | |
H45 | 0.5113 | 0.9223 | 0.6048 | 0.042* | |
C46 | 0.63705 (8) | 0.8897 (3) | 0.61202 (14) | 0.0298 (6) | |
C51 | 0.90640 (11) | 0.7399 (3) | 0.7937 (2) | 0.0547 (9) | |
H51 | 0.9330 | 0.7433 | 0.8002 | 0.066* | |
C52 | 0.88111 (9) | 0.7397 (3) | 0.72674 (17) | 0.0438 (8) | |
H52 | 0.8906 | 0.7381 | 0.6896 | 0.053* | |
C53 | 0.84135 (9) | 0.7420 (3) | 0.71551 (15) | 0.0362 (7) | |
C54 | 0.82937 (10) | 0.7414 (3) | 0.77335 (16) | 0.0465 (8) | |
H54 | 0.8030 | 0.7455 | 0.7687 | 0.056* | |
C55 | 0.85729 (13) | 0.7347 (3) | 0.83792 (18) | 0.0569 (10) | |
H55 | 0.8487 | 0.7292 | 0.8761 | 0.068* | |
C56 | 0.81220 (9) | 0.7464 (3) | 0.64308 (17) | 0.0434 (8) | |
O1W | 0.47681 (9) | 0.5376 (3) | 0.54232 (16) | 0.1017 (11) | |
H1WA | 0.4950 | 0.5482 | 0.5854 | 0.152* | |
H1WB | 0.4677 | 0.6200 | 0.5241 | 0.152* | |
O2WA | 0.4593 (9) | 0.7861 (11) | 0.4797 (10) | 0.180 (11) | 0.53 (3) |
O2WB | 0.4276 (8) | 0.7649 (15) | 0.4966 (4) | 0.125 (8) | 0.47 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.02819 (19) | 0.02970 (19) | 0.02533 (18) | 0.00133 (13) | 0.00573 (14) | −0.00109 (13) |
Zn2 | 0.0261 (2) | 0.0262 (2) | 0.0241 (2) | 0.000 | 0.00824 (18) | 0.000 |
O1 | 0.0349 (12) | 0.0500 (13) | 0.0386 (12) | −0.0014 (9) | 0.0125 (9) | 0.0029 (10) |
O2 | 0.0296 (10) | 0.0388 (11) | 0.0404 (11) | −0.0015 (8) | 0.0121 (9) | −0.0068 (9) |
O3 | 0.0403 (11) | 0.0344 (11) | 0.0352 (11) | 0.0063 (9) | 0.0160 (9) | 0.0039 (9) |
O4 | 0.0320 (10) | 0.0312 (11) | 0.0331 (10) | −0.0029 (8) | 0.0129 (9) | −0.0024 (8) |
O21 | 0.0295 (11) | 0.0572 (14) | 0.0392 (12) | 0.0014 (10) | 0.0095 (10) | −0.0099 (10) |
O22 | 0.0396 (12) | 0.0524 (13) | 0.0265 (11) | 0.0124 (10) | 0.0106 (9) | 0.0036 (9) |
O41 | 0.0405 (12) | 0.0560 (14) | 0.0297 (11) | 0.0115 (10) | 0.0143 (9) | 0.0003 (10) |
O42 | 0.0281 (11) | 0.0527 (13) | 0.0377 (11) | 0.0047 (9) | 0.0076 (9) | −0.0088 (10) |
O51 | 0.0382 (13) | 0.0693 (17) | 0.0616 (15) | 0.0006 (12) | 0.0108 (11) | 0.0081 (13) |
O52 | 0.0663 (16) | 0.0657 (16) | 0.0384 (13) | −0.0045 (13) | 0.0181 (12) | −0.0042 (12) |
N11 | 0.0321 (13) | 0.0315 (13) | 0.0270 (12) | −0.0007 (10) | 0.0051 (10) | −0.0032 (10) |
N12 | 0.0523 (17) | 0.0513 (17) | 0.0335 (14) | 0.0043 (14) | −0.0084 (13) | −0.0058 (13) |
N13 | 0.0273 (12) | 0.0320 (13) | 0.0276 (12) | 0.0038 (10) | 0.0060 (10) | 0.0033 (10) |
N14 | 0.0465 (16) | 0.0518 (17) | 0.0346 (15) | 0.0048 (13) | −0.0096 (12) | 0.0014 (13) |
N21 | 0.0295 (13) | 0.0278 (13) | 0.0295 (12) | 0.0002 (9) | 0.0091 (10) | −0.0008 (10) |
N31 | 0.0275 (12) | 0.0292 (13) | 0.0252 (12) | 0.0005 (9) | 0.0060 (10) | 0.0014 (10) |
N32 | 0.0500 (16) | 0.0435 (16) | 0.0293 (13) | −0.0004 (13) | −0.0038 (12) | −0.0010 (12) |
N41 | 0.0287 (12) | 0.0282 (12) | 0.0287 (12) | 0.0006 (9) | 0.0096 (10) | 0.0008 (10) |
N51 | 0.077 (2) | 0.0347 (16) | 0.0493 (19) | 0.0030 (15) | 0.0010 (17) | −0.0027 (13) |
S11 | 0.0676 (6) | 0.0463 (5) | 0.0462 (5) | −0.0082 (4) | 0.0025 (5) | −0.0206 (4) |
S12 | 0.0557 (6) | 0.0556 (6) | 0.0502 (5) | 0.0247 (4) | 0.0045 (4) | 0.0157 (4) |
S31 | 0.0538 (5) | 0.0391 (5) | 0.0397 (4) | 0.0046 (4) | −0.0005 (4) | 0.0142 (4) |
C13 | 0.0345 (16) | 0.0392 (17) | 0.0314 (16) | −0.0066 (13) | 0.0103 (13) | −0.0090 (13) |
C12 | 0.073 (2) | 0.0335 (18) | 0.057 (2) | 0.0056 (17) | 0.0060 (19) | −0.0107 (16) |
C11 | 0.0431 (18) | 0.0302 (16) | 0.0388 (17) | 0.0038 (13) | 0.0118 (14) | −0.0020 (13) |
C14 | 0.0405 (17) | 0.0348 (17) | 0.0368 (17) | 0.0049 (13) | 0.0121 (14) | 0.0009 (13) |
C15 | 0.070 (2) | 0.0405 (19) | 0.055 (2) | 0.0184 (18) | 0.0120 (19) | −0.0009 (16) |
C16 | 0.0283 (15) | 0.0435 (18) | 0.0345 (16) | 0.0054 (13) | 0.0079 (13) | 0.0084 (14) |
C21 | 0.0341 (16) | 0.0406 (17) | 0.0258 (14) | −0.0010 (13) | 0.0058 (12) | 0.0000 (12) |
C22 | 0.0284 (15) | 0.0398 (17) | 0.0287 (15) | 0.0010 (12) | 0.0055 (12) | 0.0010 (12) |
C23 | 0.0316 (15) | 0.0216 (14) | 0.0274 (14) | 0.0004 (11) | 0.0069 (12) | −0.0010 (11) |
C24 | 0.0343 (16) | 0.0313 (15) | 0.0223 (14) | −0.0013 (12) | 0.0050 (12) | −0.0014 (11) |
C25 | 0.0256 (14) | 0.0376 (16) | 0.0266 (15) | −0.0007 (12) | 0.0027 (12) | −0.0017 (12) |
C26 | 0.0310 (16) | 0.0250 (14) | 0.0325 (16) | 0.0015 (11) | 0.0108 (13) | 0.0017 (12) |
C33 | 0.0272 (15) | 0.0376 (16) | 0.0296 (15) | 0.0044 (12) | 0.0101 (12) | 0.0052 (13) |
C32 | 0.052 (2) | 0.0319 (17) | 0.0462 (19) | −0.0022 (14) | 0.0042 (16) | 0.0037 (14) |
C31 | 0.0289 (15) | 0.0270 (15) | 0.0353 (15) | 0.0002 (11) | 0.0101 (12) | −0.0002 (12) |
C41 | 0.0334 (16) | 0.0330 (16) | 0.0247 (14) | 0.0004 (12) | 0.0088 (12) | 0.0010 (12) |
C42 | 0.0274 (14) | 0.0326 (15) | 0.0288 (15) | 0.0016 (11) | 0.0064 (12) | 0.0013 (12) |
C43 | 0.0288 (14) | 0.0205 (13) | 0.0318 (15) | 0.0017 (11) | 0.0112 (12) | −0.0003 (11) |
C44 | 0.0362 (16) | 0.0453 (18) | 0.0238 (14) | 0.0007 (13) | 0.0110 (13) | −0.0020 (13) |
C45 | 0.0258 (15) | 0.0473 (18) | 0.0288 (15) | −0.0002 (13) | 0.0037 (12) | −0.0012 (13) |
C46 | 0.0320 (16) | 0.0270 (15) | 0.0317 (16) | 0.0003 (12) | 0.0118 (13) | −0.0021 (12) |
C51 | 0.047 (2) | 0.0375 (19) | 0.067 (2) | 0.0031 (15) | 0.0013 (18) | −0.0027 (17) |
C52 | 0.0429 (19) | 0.0402 (18) | 0.0492 (19) | 0.0016 (14) | 0.0164 (16) | 0.0006 (15) |
C53 | 0.0415 (18) | 0.0297 (16) | 0.0386 (17) | −0.0038 (13) | 0.0146 (14) | −0.0016 (13) |
C54 | 0.057 (2) | 0.0446 (19) | 0.0432 (19) | −0.0052 (16) | 0.0227 (17) | −0.0031 (15) |
C55 | 0.098 (3) | 0.0368 (19) | 0.0395 (19) | 0.0000 (19) | 0.027 (2) | −0.0038 (15) |
C56 | 0.0405 (19) | 0.050 (2) | 0.0432 (19) | −0.0126 (16) | 0.0180 (15) | 0.0048 (16) |
O1W | 0.097 (2) | 0.111 (3) | 0.0667 (19) | −0.011 (2) | −0.0161 (18) | −0.0146 (18) |
O2WA | 0.21 (2) | 0.117 (7) | 0.125 (9) | −0.023 (8) | −0.060 (12) | 0.026 (6) |
O2WB | 0.191 (17) | 0.089 (8) | 0.067 (5) | 0.036 (9) | 0.003 (6) | −0.023 (4) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.2077 (19) | N51—C55 | 1.320 (5) |
Zn1—O2 | 2.1218 (19) | N51—C51 | 1.326 (5) |
Zn1—O3 | 2.1178 (18) | S11—C12 | 1.717 (4) |
Zn1—N11 | 2.102 (2) | S11—C13 | 1.733 (3) |
Zn1—N13 | 2.140 (2) | S12—C15 | 1.720 (4) |
Zn1—N21 | 2.166 (2) | S12—C16 | 1.730 (3) |
Zn2—O4 | 2.1447 (18) | S31—C32 | 1.722 (3) |
Zn2—O4i | 2.1447 (18) | S31—C33 | 1.733 (3) |
Zn2—N31i | 2.146 (2) | C12—C11 | 1.335 (4) |
Zn2—N31 | 2.146 (2) | C12—H12 | 0.9300 |
Zn2—N41i | 2.161 (2) | C11—C14 | 1.467 (4) |
Zn2—N41 | 2.161 (2) | C14—C15 | 1.342 (4) |
O1—H1A | 0.8149 | C15—H15 | 0.9300 |
O1—H1B | 0.8467 | C21—C22 | 1.367 (4) |
O2—H2A | 0.8496 | C21—H21 | 0.9300 |
O2—H2B | 0.8363 | C22—C23 | 1.384 (4) |
O3—H3A | 0.8154 | C22—H22 | 0.9300 |
O3—H3B | 0.8434 | C23—C24 | 1.384 (4) |
O4—H4A | 0.8542 | C23—C26 | 1.516 (4) |
O4—H4B | 0.9320 | C24—C25 | 1.377 (4) |
O21—C26 | 1.250 (3) | C24—H24 | 0.9300 |
O22—C26 | 1.246 (3) | C25—H25 | 0.9300 |
O41—C46 | 1.246 (3) | C32—C31 | 1.351 (4) |
O42—C46 | 1.254 (3) | C32—H32 | 0.9300 |
O51—C56 | 1.250 (4) | C31—C31i | 1.468 (5) |
O52—C56 | 1.247 (4) | C41—C42 | 1.375 (4) |
N11—C13 | 1.314 (3) | C41—H41 | 0.9300 |
N11—C11 | 1.390 (4) | C42—C43 | 1.380 (4) |
N12—C13 | 1.329 (4) | C42—H42 | 0.9300 |
N12—H12A | 0.8261 | C43—C44 | 1.384 (4) |
N12—H12B | 0.8312 | C43—C46 | 1.518 (4) |
N13—C16 | 1.314 (3) | C44—C45 | 1.376 (4) |
N13—C14 | 1.389 (4) | C44—H44 | 0.9300 |
N14—C16 | 1.333 (4) | C45—H45 | 0.9300 |
N14—H14A | 0.8687 | C51—C52 | 1.377 (5) |
N14—H14B | 0.8174 | C51—H51 | 0.9300 |
N21—C25 | 1.340 (3) | C52—C53 | 1.382 (4) |
N21—C21 | 1.347 (3) | C52—H52 | 0.9300 |
N31—C33 | 1.318 (3) | C53—C54 | 1.385 (4) |
N31—C31 | 1.389 (3) | C53—C56 | 1.514 (4) |
N32—C33 | 1.334 (4) | C54—C55 | 1.379 (5) |
N32—H32A | 0.8368 | C54—H54 | 0.9300 |
N32—H32B | 0.8328 | C55—H55 | 0.9300 |
N41—C45 | 1.336 (3) | O1W—H1WA | 0.9187 |
N41—C41 | 1.337 (3) | O1W—H1WB | 0.9291 |
| | | |
N11—Zn1—O3 | 95.29 (8) | C12—C11—N11 | 115.4 (3) |
N11—Zn1—O2 | 173.66 (8) | C12—C11—C14 | 128.8 (3) |
O3—Zn1—O2 | 90.11 (8) | N11—C11—C14 | 115.8 (2) |
N11—Zn1—N13 | 79.16 (9) | C15—C14—N13 | 115.1 (3) |
O3—Zn1—N13 | 173.11 (8) | C15—C14—C11 | 127.9 (3) |
O2—Zn1—N13 | 95.20 (8) | N13—C14—C11 | 116.9 (2) |
N11—Zn1—N21 | 96.90 (9) | C14—C15—S12 | 110.4 (3) |
O3—Zn1—N21 | 88.00 (8) | C14—C15—H15 | 124.8 |
O2—Zn1—N21 | 86.57 (8) | S12—C15—H15 | 124.8 |
N13—Zn1—N21 | 96.67 (8) | N13—C16—N14 | 124.8 (3) |
N11—Zn1—O1 | 88.03 (8) | N13—C16—S12 | 113.6 (2) |
O3—Zn1—O1 | 87.77 (7) | N14—C16—S12 | 121.6 (2) |
O2—Zn1—O1 | 88.88 (7) | N21—C21—C22 | 123.0 (3) |
N13—Zn1—O1 | 87.96 (8) | N21—C21—H21 | 118.5 |
N21—Zn1—O1 | 173.78 (8) | C22—C21—H21 | 118.5 |
O4—Zn2—O4i | 88.32 (10) | C21—C22—C23 | 120.5 (3) |
O4—Zn2—N31i | 175.62 (8) | C21—C22—H22 | 119.8 |
O4i—Zn2—N31i | 96.02 (8) | C23—C22—H22 | 119.8 |
O4—Zn2—N31 | 96.02 (8) | C22—C23—C24 | 116.8 (3) |
O4i—Zn2—N31 | 175.62 (8) | C22—C23—C26 | 121.7 (2) |
N31i—Zn2—N31 | 79.64 (12) | C24—C23—C26 | 121.5 (2) |
O4—Zn2—N41i | 90.78 (8) | C25—C24—C23 | 119.6 (2) |
O4i—Zn2—N41i | 88.38 (8) | C25—C24—H24 | 120.2 |
N31i—Zn2—N41i | 89.95 (8) | C23—C24—H24 | 120.2 |
N31—Zn2—N41i | 90.95 (8) | N21—C25—C24 | 123.5 (2) |
O4—Zn2—N41 | 88.38 (8) | N21—C25—H25 | 118.2 |
O4i—Zn2—N41 | 90.78 (8) | C24—C25—H25 | 118.2 |
N31i—Zn2—N41 | 90.95 (8) | O22—C26—O21 | 125.3 (3) |
N31—Zn2—N41 | 89.95 (8) | O22—C26—C23 | 117.4 (2) |
N41i—Zn2—N41 | 178.83 (12) | O21—C26—C23 | 117.3 (2) |
Zn1—O1—H1A | 130.3 | N31—C33—N32 | 124.7 (3) |
Zn1—O1—H1B | 114.4 | N31—C33—S31 | 113.9 (2) |
H1A—O1—H1B | 111.0 | N32—C33—S31 | 121.4 (2) |
Zn1—O2—H2A | 121.6 | C31—C32—S31 | 110.4 (2) |
Zn1—O2—H2B | 116.2 | C31—C32—H32 | 124.8 |
H2A—O2—H2B | 110.8 | S31—C32—H32 | 124.8 |
Zn1—O3—H3A | 120.8 | C32—C31—N31 | 115.2 (3) |
Zn1—O3—H3B | 118.4 | C32—C31—C31i | 127.70 (18) |
H3A—O3—H3B | 99.1 | N31—C31—C31i | 117.06 (15) |
Zn2—O4—H4A | 116.9 | N41—C41—C42 | 123.6 (2) |
Zn2—O4—H4B | 103.8 | N41—C41—H41 | 118.2 |
H4A—O4—H4B | 106.8 | C42—C41—H41 | 118.2 |
C13—N11—C11 | 110.9 (2) | C41—C42—C43 | 119.3 (3) |
C13—N11—Zn1 | 134.3 (2) | C41—C42—H42 | 120.3 |
C11—N11—Zn1 | 114.85 (18) | C43—C42—H42 | 120.3 |
C13—N12—H12A | 116.9 | C42—C43—C44 | 117.5 (2) |
C13—N12—H12B | 119.5 | C42—C43—C46 | 121.3 (2) |
H12A—N12—H12B | 123.6 | C44—C43—C46 | 121.2 (2) |
C16—N13—C14 | 111.2 (2) | C45—C44—C43 | 119.5 (2) |
C16—N13—Zn1 | 135.6 (2) | C45—C44—H44 | 120.2 |
C14—N13—Zn1 | 113.01 (17) | C43—C44—H44 | 120.2 |
C16—N14—H14A | 117.8 | N41—C45—C44 | 123.3 (3) |
C16—N14—H14B | 114.9 | N41—C45—H45 | 118.4 |
H14A—N14—H14B | 126.6 | C44—C45—H45 | 118.4 |
C25—N21—C21 | 116.4 (2) | O41—C46—O42 | 126.1 (3) |
C25—N21—Zn1 | 120.79 (18) | O41—C46—C43 | 116.7 (2) |
C21—N21—Zn1 | 122.38 (18) | O42—C46—C43 | 117.1 (2) |
C33—N31—C31 | 110.9 (2) | N51—C51—C52 | 124.4 (3) |
C33—N31—Zn2 | 135.87 (19) | N51—C51—H51 | 117.8 |
C31—N31—Zn2 | 112.47 (16) | C52—C51—H51 | 117.8 |
C33—N32—H32A | 117.3 | C51—C52—C53 | 119.0 (3) |
C33—N32—H32B | 122.4 | C51—C52—H52 | 120.5 |
H32A—N32—H32B | 119.7 | C53—C52—H52 | 120.5 |
C45—N41—C41 | 116.7 (2) | C52—C53—C54 | 117.1 (3) |
C45—N41—Zn2 | 123.32 (18) | C52—C53—C56 | 121.3 (3) |
C41—N41—Zn2 | 119.93 (18) | C54—C53—C56 | 121.5 (3) |
C55—N51—C51 | 115.9 (3) | C55—C54—C53 | 118.8 (3) |
C12—S11—C13 | 89.62 (15) | C55—C54—H54 | 120.6 |
C15—S12—C16 | 89.71 (15) | C53—C54—H54 | 120.6 |
C32—S31—C33 | 89.61 (14) | N51—C55—C54 | 124.6 (3) |
N11—C13—N12 | 124.7 (3) | N51—C55—H55 | 117.7 |
N11—C13—S11 | 113.5 (2) | C54—C55—H55 | 117.7 |
N12—C13—S11 | 121.8 (2) | O52—C56—O51 | 125.4 (3) |
C11—C12—S11 | 110.6 (3) | O52—C56—C53 | 117.3 (3) |
C11—C12—H12 | 124.7 | O51—C56—C53 | 117.3 (3) |
S11—C12—H12 | 124.7 | H1WA—O1W—H1WB | 109.2 |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O52 | 0.81 | 2.08 | 2.856 (3) | 161 |
O1—H1B···O51ii | 0.85 | 2.02 | 2.859 (3) | 172 |
O2—H2A···O51 | 0.85 | 1.85 | 2.702 (4) | 179 |
O2—H2B···O42 | 0.84 | 1.84 | 2.660 (3) | 166 |
O3—H3A···O52ii | 0.82 | 1.89 | 2.686 (3) | 165 |
O3—H3B···O41 | 0.84 | 1.79 | 2.634 (3) | 177 |
O4—H4A···O22i | 0.85 | 1.85 | 2.699 (3) | 173 |
O4—H4B···O21 | 0.93 | 1.81 | 2.741 (3) | 175 |
O1W—H1WA···O21 | 0.92 | 1.81 | 2.720 (4) | 168 |
O1W—H1WB···O2WA | 0.93 | 1.89 | 2.799 (14) | 167 |
O1W—H1WB···O2WB | 0.93 | 2.01 | 2.873 (19) | 154 |
N12—H12A···O3 | 0.83 | 2.22 | 2.972 (4) | 151 |
N12—H12B···O22iii | 0.83 | 2.00 | 2.803 (3) | 161 |
N14—H14A···O2 | 0.87 | 2.27 | 3.061 (4) | 151 |
N14—H14B···O42iv | 0.82 | 2.12 | 2.929 (3) | 171 |
N32—H32A···O4 | 0.84 | 2.35 | 3.117 (3) | 153 |
N32—H32B···O41v | 0.83 | 2.19 | 2.980 (3) | 159 |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+3/2, −y+3/2, −z+1; (iii) x, −y+1, z−1/2; (iv) −x+3/2, y−1/2, −z+3/2; (v) −x+1, −y+2, −z+1. |