Copper(II) coordination polymers have attracted considerable interest due to their catalytic, adsorption, luminescence and magnetic properties. The reactions of copper(II) with 2-amino-4-sulfobenzoic acid (H
2asba) in the presence/absence of the auxiliary chelating ligand 1,10-phenanthroline (phen) under ambient conditions yielded two supramolecular coordination polymers, namely (3-amino-4-carboxybenzene-1-sulfonato-
O1)bis(1,10-phenanthroline-
2N,
N')copper(II) 3-amino-4-carboxybenzene-1-sulfonate monohydrate, [Cu(C
7H
6N
2O
5S)(C
12H
8N
2)
2](C
7H
6N
2O
5S)·H
2O, (1), and
catena-poly[[diaquacopper(II)]-
-3-amino-4-carboxylatobenzene-1-sulfonato-
2O4:
O4'], [Cu(C
7H
6N
2O
5S)(H
2O)
2]
n, (2). The products were characterized by FT-IR spectroscopy, thermogravimetric analysis (TGA), solid-state UV-Vis spectroscopy and single-crystal X-ray diffraction analysis, as well as by variable-temperature powder X-ray diffraction analysis (VT-PXRD). Intermolecular
-
stacking interactions in (1) link the mononuclear copper(II) cation units into a supramolecular polymeric chain, which is further extended into a supramolecular double chain through interchain hydrogen bonds. Supramolecular double chains are then extended into a two-dimensional supramolecular double layer through hydrogen bonds between the lattice Hasba
- anions, H
2O molecules and double chains. Left- and right-handed 2
1 helices formed by the Hasba
- anions are arranged alternately within the two-dimensional supramolecular double layers. Complex (2) exhibits a polymeric chain which is further extended into a three-dimensional supramolecular network through interchain hydrogen bonds. Complex (1) shows a reversible dehydration-rehydration behaviour, while complex (2) shows an irreversible dehydration-rehydration behaviour.
Supporting information
CCDC references: 1406470; 1406469
For both compounds, data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).
(zl9) (3-Amino-4-carboxybenzene-1-sulfonato-
κO1)bis(1,10-phenanthroline-
κ2N,
N')copper(II)
3-amino-4-carboxybenzene-1-sulfonate monohydrate
top
Crystal data top
[Cu(C7H6N2O5S)(C12H8N2)2](C7H6N2O5S)·H2O | F(000) = 1796 |
Mr = 874.37 | Dx = 1.625 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 9881 reflections |
a = 11.7178 (14) Å | θ = 2.5–26.9° |
b = 8.2765 (9) Å | µ = 0.80 mm−1 |
c = 37.404 (4) Å | T = 296 K |
β = 99.806 (5)° | Massive, green |
V = 3574.5 (7) Å3 | 0.25 × 0.2 × 0.15 mm |
Z = 4 | |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 8212 independent reflections |
Radiation source: fine-focus sealed tube | 6137 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
phi and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2003) | h = −15→15 |
Tmin = 0.825, Tmax = 0.887 | k = −10→10 |
52816 measured reflections | l = −48→48 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0505P)2 + 2.1869P] where P = (Fo2 + 2Fc2)/3 |
8212 reflections | (Δ/σ)max = 0.001 |
527 parameters | Δρmax = 0.66 e Å−3 |
10 restraints | Δρmin = −0.46 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 | |
C1 | −0.1607 (2) | 0.7348 (4) | 0.90577 (8) | 0.0499 (7) | |
H1 | −0.1299 | 0.6893 | 0.9281 | 0.060* | |
C2 | −0.2534 (3) | 0.8428 (4) | 0.90396 (11) | 0.0669 (10) | |
H2 | −0.2825 | 0.8697 | 0.9248 | 0.080* | |
C3 | −0.3006 (3) | 0.9083 (4) | 0.87138 (12) | 0.0699 (10) | |
H3 | −0.3615 | 0.9813 | 0.8700 | 0.084* | |
C4 | −0.2579 (2) | 0.8659 (3) | 0.84020 (9) | 0.0555 (8) | |
C5 | −0.1637 (2) | 0.7599 (3) | 0.84444 (7) | 0.0399 (6) | |
C6 | −0.1142 (2) | 0.7141 (3) | 0.81373 (6) | 0.0393 (6) | |
C7 | −0.1639 (3) | 0.7655 (3) | 0.77846 (8) | 0.0540 (8) | |
C8 | −0.2604 (3) | 0.8717 (4) | 0.77519 (11) | 0.0749 (11) | |
H8 | −0.2939 | 0.9084 | 0.7523 | 0.090* | |
C9 | −0.3041 (3) | 0.9202 (4) | 0.80387 (12) | 0.0740 (11) | |
H9 | −0.3665 | 0.9913 | 0.8005 | 0.089* | |
C10 | −0.1135 (3) | 0.7049 (4) | 0.74997 (7) | 0.0652 (10) | |
H10 | −0.1450 | 0.7326 | 0.7262 | 0.078* | |
C11 | −0.0206 (3) | 0.6073 (4) | 0.75614 (7) | 0.0646 (9) | |
H11 | 0.0125 | 0.5681 | 0.7370 | 0.078* | |
C12 | 0.0249 (3) | 0.5665 (4) | 0.79152 (7) | 0.0566 (8) | |
H12 | 0.0898 | 0.5002 | 0.7958 | 0.068* | |
C13 | 0.2414 (2) | 0.7559 (3) | 0.85428 (7) | 0.0474 (6) | |
H13 | 0.2015 | 0.7727 | 0.8309 | 0.057* | |
C14 | 0.3508 (3) | 0.8207 (4) | 0.86379 (8) | 0.0552 (7) | |
H14 | 0.3835 | 0.8794 | 0.8469 | 0.066* | |
C15 | 0.4107 (2) | 0.7989 (4) | 0.89785 (8) | 0.0542 (7) | |
H15 | 0.4844 | 0.8429 | 0.9044 | 0.065* | |
C16 | 0.3610 (2) | 0.7094 (3) | 0.92323 (7) | 0.0418 (6) | |
C17 | 0.2496 (2) | 0.6489 (3) | 0.91134 (6) | 0.0348 (5) | |
C18 | 0.1926 (2) | 0.5594 (3) | 0.93577 (6) | 0.0331 (5) | |
C19 | 0.2489 (2) | 0.5292 (3) | 0.97122 (6) | 0.0380 (6) | |
C20 | 0.3622 (2) | 0.5941 (4) | 0.98251 (7) | 0.0482 (7) | |
H20 | 0.3998 | 0.5772 | 1.0062 | 0.058* | |
C21 | 0.4151 (2) | 0.6785 (4) | 0.95976 (8) | 0.0516 (7) | |
H21 | 0.4892 | 0.7184 | 0.9679 | 0.062* | |
C22 | 0.1885 (2) | 0.4350 (3) | 0.99327 (7) | 0.0453 (6) | |
H22 | 0.2219 | 0.4123 | 1.0171 | 0.054* | |
C23 | 0.0813 (2) | 0.3776 (3) | 0.97963 (7) | 0.0452 (6) | |
H23 | 0.0417 | 0.3139 | 0.9940 | 0.054* | |
C24 | 0.0306 (2) | 0.4147 (3) | 0.94395 (6) | 0.0410 (6) | |
H24 | −0.0429 | 0.3748 | 0.9349 | 0.049* | |
C25 | 0.21565 (19) | 0.0117 (3) | 0.96723 (6) | 0.0306 (5) | |
C26 | 0.28963 (18) | 0.0983 (3) | 0.94803 (6) | 0.0312 (5) | |
C27 | 0.24465 (19) | 0.1496 (3) | 0.91263 (6) | 0.0327 (5) | |
H27 | 0.2918 | 0.2070 | 0.8995 | 0.039* | |
C28 | 0.13309 (19) | 0.1165 (3) | 0.89722 (6) | 0.0320 (5) | |
C29 | 0.0589 (2) | 0.0316 (3) | 0.91592 (6) | 0.0386 (6) | |
H29 | −0.0173 | 0.0106 | 0.9053 | 0.046* | |
C30 | 0.1013 (2) | −0.0202 (3) | 0.95046 (6) | 0.0372 (5) | |
H30 | 0.0530 | −0.0779 | 0.9631 | 0.045* | |
C31 | 0.2570 (2) | −0.0429 (3) | 1.00470 (6) | 0.0362 (5) | |
C32 | 0.6343 (2) | 0.4615 (3) | 0.78522 (6) | 0.0342 (5) | |
C33 | 0.71962 (19) | 0.3591 (3) | 0.80419 (6) | 0.0349 (5) | |
C34 | 0.72128 (19) | 0.3344 (3) | 0.84147 (6) | 0.0358 (5) | |
H34 | 0.7764 | 0.2661 | 0.8544 | 0.043* | |
C35 | 0.64237 (19) | 0.4101 (3) | 0.85886 (6) | 0.0319 (5) | |
C36 | 0.5600 (2) | 0.5137 (3) | 0.84060 (6) | 0.0404 (6) | |
H36 | 0.5078 | 0.5659 | 0.8528 | 0.048* | |
C37 | 0.5565 (2) | 0.5386 (3) | 0.80387 (7) | 0.0403 (6) | |
H37 | 0.5011 | 0.6080 | 0.7914 | 0.048* | |
C38 | 0.6296 (2) | 0.4897 (3) | 0.74595 (7) | 0.0420 (6) | |
Cu1 | 0.03046 (3) | 0.56098 (4) | 0.871179 (7) | 0.03951 (10) | |
N1 | −0.11532 (16) | 0.6948 (3) | 0.87692 (5) | 0.0385 (5) | |
N2 | −0.02020 (19) | 0.6180 (3) | 0.81970 (5) | 0.0412 (5) | |
N3 | 0.19067 (17) | 0.6703 (2) | 0.87720 (5) | 0.0377 (5) | |
N4 | 0.08425 (17) | 0.5048 (3) | 0.92277 (5) | 0.0359 (4) | |
N5 | 0.40098 (17) | 0.1339 (3) | 0.96161 (6) | 0.0492 (6) | |
H5A | 0.4423 | 0.1866 | 0.9487 | 0.059* | |
H5B | 0.4306 | 0.1039 | 0.9832 | 0.059* | |
N6 | 0.8009 (2) | 0.2846 (3) | 0.78815 (6) | 0.0600 (7) | |
H6A | 0.8521 | 0.2238 | 0.8008 | 0.072* | |
H6B | 0.8013 | 0.2983 | 0.7654 | 0.072* | |
O1 | −0.00372 (14) | 0.3183 (2) | 0.85908 (4) | 0.0420 (4) | |
O2 | 0.17531 (16) | 0.2594 (3) | 0.83907 (5) | 0.0557 (5) | |
O3 | 0.01945 (19) | 0.0602 (2) | 0.83264 (5) | 0.0588 (5) | |
O4 | 0.35162 (15) | −0.0101 (3) | 1.02202 (5) | 0.0514 (5) | |
O5 | 0.18111 (15) | −0.1323 (3) | 1.01846 (5) | 0.0514 (5) | |
H5 | 0.2119 | −0.1693 | 1.0381 | 0.077* | |
O6 | 0.53864 (16) | 0.2549 (3) | 0.90272 (5) | 0.0599 (6) | |
O7 | 0.6247 (2) | 0.5106 (3) | 0.92356 (5) | 0.0691 (6) | |
O8 | 0.74524 (15) | 0.2787 (3) | 0.91882 (5) | 0.0567 (5) | |
O9 | 0.6873 (2) | 0.4156 (3) | 0.72731 (5) | 0.0688 (6) | |
O10 | 0.55839 (17) | 0.6071 (3) | 0.73244 (5) | 0.0531 (5) | |
H10A | 0.5689 | 0.6288 | 0.7119 | 0.080* | |
O1W | 0.40628 (18) | 0.1781 (3) | 0.83336 (5) | 0.0614 (6) | |
H1WB | 0.4440 | 0.2188 | 0.8516 | 0.090 (13)* | |
H1WA | 0.3330 | 0.2050 | 0.8377 | 0.098 (13)* | |
S1 | 0.07821 (5) | 0.19073 (8) | 0.853224 (15) | 0.03664 (15) | |
S2 | 0.63718 (5) | 0.36177 (8) | 0.905053 (15) | 0.03748 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0459 (15) | 0.0545 (17) | 0.0518 (16) | −0.0118 (13) | 0.0156 (12) | −0.0132 (13) |
C2 | 0.0568 (19) | 0.057 (2) | 0.096 (3) | −0.0108 (16) | 0.0413 (19) | −0.0264 (19) |
C3 | 0.0443 (17) | 0.0437 (18) | 0.126 (3) | 0.0001 (14) | 0.026 (2) | −0.001 (2) |
C4 | 0.0359 (14) | 0.0391 (15) | 0.090 (2) | −0.0042 (12) | 0.0073 (14) | 0.0046 (15) |
C5 | 0.0348 (12) | 0.0313 (13) | 0.0503 (15) | −0.0074 (10) | −0.0024 (11) | −0.0001 (11) |
C6 | 0.0468 (14) | 0.0309 (12) | 0.0354 (13) | −0.0101 (11) | −0.0066 (11) | 0.0052 (10) |
C7 | 0.0608 (17) | 0.0405 (15) | 0.0519 (17) | −0.0184 (13) | −0.0154 (14) | 0.0183 (13) |
C8 | 0.066 (2) | 0.065 (2) | 0.080 (3) | −0.0143 (18) | −0.0271 (19) | 0.032 (2) |
C9 | 0.0441 (17) | 0.0499 (19) | 0.118 (3) | 0.0014 (14) | −0.0156 (19) | 0.029 (2) |
C10 | 0.105 (3) | 0.0579 (19) | 0.0252 (14) | −0.0314 (19) | −0.0090 (15) | 0.0113 (13) |
C11 | 0.112 (3) | 0.0566 (19) | 0.0251 (14) | −0.008 (2) | 0.0110 (16) | 0.0040 (13) |
C12 | 0.091 (2) | 0.0520 (17) | 0.0293 (13) | 0.0077 (16) | 0.0161 (14) | 0.0033 (12) |
C13 | 0.0567 (16) | 0.0494 (16) | 0.0400 (14) | 0.0072 (13) | 0.0195 (12) | 0.0072 (12) |
C14 | 0.0612 (18) | 0.0520 (17) | 0.0601 (19) | −0.0001 (14) | 0.0321 (15) | 0.0072 (14) |
C15 | 0.0455 (15) | 0.0560 (17) | 0.066 (2) | −0.0050 (13) | 0.0225 (14) | −0.0082 (15) |
C16 | 0.0391 (13) | 0.0437 (14) | 0.0443 (14) | 0.0012 (11) | 0.0120 (11) | −0.0084 (12) |
C17 | 0.0389 (12) | 0.0345 (13) | 0.0321 (12) | 0.0055 (10) | 0.0095 (10) | −0.0038 (10) |
C18 | 0.0383 (12) | 0.0341 (12) | 0.0267 (11) | 0.0047 (10) | 0.0052 (9) | −0.0040 (10) |
C19 | 0.0448 (13) | 0.0414 (14) | 0.0273 (12) | 0.0093 (11) | 0.0047 (10) | −0.0045 (10) |
C20 | 0.0435 (14) | 0.0635 (18) | 0.0343 (14) | 0.0085 (13) | −0.0026 (11) | −0.0078 (13) |
C21 | 0.0382 (14) | 0.0652 (19) | 0.0493 (16) | −0.0006 (13) | 0.0018 (12) | −0.0166 (14) |
C22 | 0.0595 (17) | 0.0519 (16) | 0.0240 (12) | 0.0101 (13) | 0.0055 (11) | 0.0013 (11) |
C23 | 0.0583 (16) | 0.0501 (15) | 0.0302 (13) | 0.0011 (13) | 0.0159 (12) | 0.0032 (11) |
C24 | 0.0445 (14) | 0.0481 (15) | 0.0311 (12) | −0.0046 (12) | 0.0087 (10) | −0.0020 (11) |
C25 | 0.0341 (11) | 0.0342 (12) | 0.0229 (11) | 0.0068 (10) | 0.0030 (9) | 0.0038 (9) |
C26 | 0.0291 (11) | 0.0383 (13) | 0.0258 (11) | 0.0044 (9) | 0.0035 (9) | 0.0017 (9) |
C27 | 0.0330 (12) | 0.0405 (13) | 0.0253 (11) | 0.0022 (10) | 0.0073 (9) | 0.0053 (10) |
C28 | 0.0362 (12) | 0.0340 (12) | 0.0245 (11) | 0.0028 (10) | 0.0016 (9) | 0.0025 (9) |
C29 | 0.0329 (12) | 0.0451 (14) | 0.0347 (13) | −0.0053 (11) | −0.0034 (10) | 0.0058 (11) |
C30 | 0.0368 (12) | 0.0409 (14) | 0.0331 (12) | −0.0044 (11) | 0.0037 (10) | 0.0086 (10) |
C31 | 0.0378 (13) | 0.0443 (14) | 0.0271 (11) | 0.0058 (11) | 0.0068 (10) | 0.0050 (10) |
C32 | 0.0388 (12) | 0.0371 (13) | 0.0252 (11) | −0.0092 (10) | 0.0015 (9) | 0.0025 (10) |
C33 | 0.0331 (12) | 0.0409 (13) | 0.0303 (12) | −0.0056 (10) | 0.0045 (9) | 0.0017 (10) |
C34 | 0.0324 (12) | 0.0444 (14) | 0.0294 (12) | −0.0021 (10) | 0.0023 (9) | 0.0100 (10) |
C35 | 0.0349 (12) | 0.0366 (13) | 0.0233 (11) | −0.0082 (10) | 0.0028 (9) | 0.0037 (9) |
C36 | 0.0477 (14) | 0.0409 (14) | 0.0336 (13) | 0.0042 (11) | 0.0102 (11) | 0.0032 (11) |
C37 | 0.0445 (14) | 0.0412 (15) | 0.0333 (13) | 0.0012 (11) | 0.0007 (10) | 0.0073 (11) |
C38 | 0.0437 (14) | 0.0515 (16) | 0.0285 (12) | −0.0087 (12) | −0.0002 (11) | 0.0037 (12) |
Cu1 | 0.04311 (18) | 0.0542 (2) | 0.02061 (15) | 0.00513 (14) | 0.00367 (12) | 0.00409 (13) |
N1 | 0.0362 (10) | 0.0426 (12) | 0.0371 (11) | −0.0058 (9) | 0.0076 (9) | −0.0072 (9) |
N2 | 0.0578 (13) | 0.0398 (11) | 0.0246 (10) | 0.0027 (10) | 0.0033 (9) | 0.0031 (9) |
N3 | 0.0440 (11) | 0.0402 (11) | 0.0298 (10) | 0.0045 (9) | 0.0092 (9) | 0.0033 (9) |
N4 | 0.0385 (11) | 0.0465 (12) | 0.0222 (9) | −0.0008 (9) | 0.0039 (8) | −0.0001 (9) |
N5 | 0.0314 (11) | 0.0784 (17) | 0.0351 (11) | −0.0063 (11) | −0.0018 (9) | 0.0149 (11) |
N6 | 0.0578 (14) | 0.0846 (19) | 0.0399 (13) | 0.0161 (14) | 0.0147 (11) | 0.0110 (13) |
O1 | 0.0413 (9) | 0.0471 (10) | 0.0346 (9) | 0.0051 (8) | −0.0024 (7) | 0.0062 (8) |
O2 | 0.0495 (11) | 0.0855 (15) | 0.0327 (10) | 0.0056 (10) | 0.0091 (8) | 0.0190 (10) |
O3 | 0.0849 (14) | 0.0521 (12) | 0.0318 (10) | −0.0050 (10) | −0.0119 (9) | −0.0044 (9) |
O4 | 0.0422 (10) | 0.0790 (14) | 0.0297 (9) | −0.0033 (10) | −0.0033 (8) | 0.0132 (9) |
O5 | 0.0475 (10) | 0.0744 (13) | 0.0304 (9) | −0.0044 (10) | 0.0010 (8) | 0.0218 (9) |
O6 | 0.0489 (11) | 0.0942 (16) | 0.0362 (10) | −0.0267 (11) | 0.0061 (8) | 0.0155 (10) |
O7 | 0.1083 (18) | 0.0675 (14) | 0.0323 (10) | 0.0017 (13) | 0.0145 (11) | −0.0055 (10) |
O8 | 0.0478 (10) | 0.0874 (15) | 0.0348 (10) | 0.0050 (10) | 0.0069 (8) | 0.0269 (10) |
O9 | 0.0830 (15) | 0.0944 (17) | 0.0296 (10) | 0.0211 (13) | 0.0112 (10) | 0.0043 (10) |
O10 | 0.0569 (11) | 0.0682 (13) | 0.0318 (9) | 0.0012 (10) | 0.0007 (8) | 0.0163 (9) |
O1W | 0.0588 (12) | 0.0852 (16) | 0.0415 (11) | −0.0202 (11) | 0.0129 (9) | −0.0246 (11) |
S1 | 0.0407 (3) | 0.0453 (4) | 0.0215 (3) | 0.0019 (3) | −0.0015 (2) | 0.0044 (2) |
S2 | 0.0386 (3) | 0.0510 (4) | 0.0225 (3) | −0.0065 (3) | 0.0043 (2) | 0.0059 (3) |
Geometric parameters (Å, º) top
C1—N1 | 1.324 (3) | C25—C30 | 1.404 (3) |
C1—C2 | 1.399 (4) | C25—C26 | 1.412 (3) |
C1—H1 | 0.9300 | C25—C31 | 1.474 (3) |
C2—C3 | 1.362 (5) | C26—N5 | 1.350 (3) |
C2—H2 | 0.9300 | C26—C27 | 1.405 (3) |
C3—C4 | 1.390 (5) | C27—C28 | 1.364 (3) |
C3—H3 | 0.9300 | C27—H27 | 0.9300 |
C4—C5 | 1.398 (4) | C28—C29 | 1.395 (3) |
C4—C9 | 1.446 (5) | C28—S1 | 1.772 (2) |
C5—N1 | 1.361 (3) | C29—C30 | 1.371 (3) |
C5—C6 | 1.423 (4) | C29—H29 | 0.9300 |
C6—N2 | 1.346 (3) | C30—H30 | 0.9300 |
C6—C7 | 1.414 (3) | C31—O4 | 1.216 (3) |
C7—C10 | 1.396 (5) | C31—O5 | 1.327 (3) |
C7—C8 | 1.422 (5) | C32—C37 | 1.394 (3) |
C8—C9 | 1.327 (5) | C32—C33 | 1.407 (3) |
C8—H8 | 0.9300 | C32—C38 | 1.479 (3) |
C9—H9 | 0.9300 | C33—N6 | 1.357 (3) |
C10—C11 | 1.344 (5) | C33—C34 | 1.407 (3) |
C10—H10 | 0.9300 | C34—C35 | 1.370 (3) |
C11—C12 | 1.382 (4) | C34—H34 | 0.9300 |
C11—H11 | 0.9300 | C35—C36 | 1.382 (3) |
C12—N2 | 1.327 (3) | C35—S2 | 1.784 (2) |
C12—H12 | 0.9300 | C36—C37 | 1.383 (3) |
C13—N3 | 1.327 (3) | C36—H36 | 0.9300 |
C13—C14 | 1.380 (4) | C37—H37 | 0.9300 |
C13—H13 | 0.9300 | C38—O9 | 1.217 (3) |
C14—C15 | 1.358 (4) | C38—O10 | 1.323 (3) |
C14—H14 | 0.9300 | Cu1—N2 | 1.9731 (19) |
C15—C16 | 1.406 (4) | Cu1—N4 | 1.9806 (18) |
C15—H15 | 0.9300 | Cu1—N3 | 2.062 (2) |
C16—C17 | 1.399 (3) | Cu1—N1 | 2.077 (2) |
C16—C21 | 1.428 (4) | Cu1—O1 | 2.0824 (18) |
C17—N3 | 1.356 (3) | N5—H5A | 0.8600 |
C17—C18 | 1.427 (3) | N5—H5B | 0.8600 |
C18—N4 | 1.357 (3) | N6—H6A | 0.8600 |
C18—C19 | 1.399 (3) | N6—H6B | 0.8600 |
C19—C22 | 1.409 (4) | O1—S1 | 1.4686 (18) |
C19—C20 | 1.428 (4) | O2—S1 | 1.4501 (19) |
C20—C21 | 1.333 (4) | O3—S1 | 1.4332 (19) |
C20—H20 | 0.9300 | O5—H5 | 0.8200 |
C21—H21 | 0.9300 | O6—S2 | 1.4450 (19) |
C22—C23 | 1.359 (4) | O7—S2 | 1.432 (2) |
C22—H22 | 0.9300 | O8—S2 | 1.4558 (19) |
C23—C24 | 1.399 (3) | O10—H10A | 0.8200 |
C23—H23 | 0.9300 | O1W—H1WB | 0.8209 |
C24—N4 | 1.323 (3) | O1W—H1WA | 0.9278 |
C24—H24 | 0.9300 | | |
| | | |
N1—C1—C2 | 122.4 (3) | C28—C27—H27 | 119.4 |
N1—C1—H1 | 118.8 | C26—C27—H27 | 119.4 |
C2—C1—H1 | 118.8 | C27—C28—C29 | 121.6 (2) |
C3—C2—C1 | 119.4 (3) | C27—C28—S1 | 119.56 (17) |
C3—C2—H2 | 120.3 | C29—C28—S1 | 118.81 (17) |
C1—C2—H2 | 120.3 | C30—C29—C28 | 118.2 (2) |
C2—C3—C4 | 120.1 (3) | C30—C29—H29 | 120.9 |
C2—C3—H3 | 120.0 | C28—C29—H29 | 120.9 |
C4—C3—H3 | 120.0 | C29—C30—C25 | 121.8 (2) |
C3—C4—C5 | 117.0 (3) | C29—C30—H30 | 119.1 |
C3—C4—C9 | 125.4 (3) | C25—C30—H30 | 119.1 |
C5—C4—C9 | 117.6 (3) | O4—C31—O5 | 121.9 (2) |
N1—C5—C4 | 123.4 (3) | O4—C31—C25 | 124.1 (2) |
N1—C5—C6 | 116.8 (2) | O5—C31—C25 | 114.0 (2) |
C4—C5—C6 | 119.9 (3) | C37—C32—C33 | 119.5 (2) |
N2—C6—C7 | 121.9 (3) | C37—C32—C38 | 120.5 (2) |
N2—C6—C5 | 117.2 (2) | C33—C32—C38 | 120.0 (2) |
C7—C6—C5 | 120.9 (3) | N6—C33—C34 | 118.7 (2) |
C10—C7—C6 | 116.3 (3) | N6—C33—C32 | 122.9 (2) |
C10—C7—C8 | 126.2 (3) | C34—C33—C32 | 118.4 (2) |
C6—C7—C8 | 117.5 (3) | C35—C34—C33 | 120.5 (2) |
C9—C8—C7 | 121.9 (3) | C35—C34—H34 | 119.7 |
C9—C8—H8 | 119.1 | C33—C34—H34 | 119.7 |
C7—C8—H8 | 119.1 | C34—C35—C36 | 121.4 (2) |
C8—C9—C4 | 122.1 (3) | C34—C35—S2 | 119.63 (17) |
C8—C9—H9 | 118.9 | C36—C35—S2 | 118.80 (18) |
C4—C9—H9 | 118.9 | C35—C36—C37 | 119.0 (2) |
C11—C10—C7 | 121.4 (3) | C35—C36—H36 | 120.5 |
C11—C10—H10 | 119.3 | C37—C36—H36 | 120.5 |
C7—C10—H10 | 119.3 | C36—C37—C32 | 121.1 (2) |
C10—C11—C12 | 118.7 (3) | C36—C37—H37 | 119.4 |
C10—C11—H11 | 120.6 | C32—C37—H37 | 119.4 |
C12—C11—H11 | 120.6 | O9—C38—O10 | 121.8 (2) |
N2—C12—C11 | 122.8 (3) | O9—C38—C32 | 124.0 (2) |
N2—C12—H12 | 118.6 | O10—C38—C32 | 114.2 (2) |
C11—C12—H12 | 118.6 | N2—Cu1—N4 | 178.95 (9) |
N3—C13—C14 | 122.7 (3) | N2—Cu1—N3 | 96.81 (9) |
N3—C13—H13 | 118.7 | N4—Cu1—N3 | 82.18 (8) |
C14—C13—H13 | 118.7 | N2—Cu1—N1 | 81.80 (8) |
C15—C14—C13 | 120.0 (3) | N4—Cu1—N1 | 98.94 (8) |
C15—C14—H14 | 120.0 | N2—Cu1—O1 | 90.22 (8) |
C13—C14—H14 | 120.0 | N4—Cu1—O1 | 90.15 (8) |
C14—C15—C16 | 119.7 (3) | N3—Cu1—O1 | 125.80 (7) |
C14—C15—H15 | 120.1 | N1—Cu1—O1 | 113.92 (7) |
C16—C15—H15 | 120.1 | N3—Cu1—N1 | 120.28 (8) |
C17—C16—C15 | 116.5 (2) | C1—N1—C5 | 117.7 (2) |
C17—C16—C21 | 118.6 (2) | C1—N1—Cu1 | 132.00 (19) |
C15—C16—C21 | 124.9 (3) | C5—N1—Cu1 | 110.07 (16) |
N3—C17—C16 | 123.4 (2) | C12—N2—C6 | 118.9 (2) |
N3—C17—C18 | 116.9 (2) | C12—N2—Cu1 | 127.17 (19) |
C16—C17—C18 | 119.7 (2) | C6—N2—Cu1 | 113.89 (16) |
N4—C18—C19 | 122.8 (2) | C13—N3—C17 | 117.8 (2) |
N4—C18—C17 | 117.0 (2) | C13—N3—Cu1 | 131.52 (19) |
C19—C18—C17 | 120.2 (2) | C17—N3—Cu1 | 110.68 (15) |
C18—C19—C22 | 116.8 (2) | C24—N4—C18 | 119.0 (2) |
C18—C19—C20 | 118.5 (2) | C24—N4—Cu1 | 127.68 (17) |
C22—C19—C20 | 124.7 (2) | C18—N4—Cu1 | 113.20 (15) |
C21—C20—C19 | 121.2 (2) | C26—N5—H5A | 120.0 |
C21—C20—H20 | 119.4 | C26—N5—H5B | 120.0 |
C19—C20—H20 | 119.4 | H5A—N5—H5B | 120.0 |
C20—C21—C16 | 121.7 (3) | C33—N6—H6A | 120.0 |
C20—C21—H21 | 119.1 | C33—N6—H6B | 120.0 |
C16—C21—H21 | 119.1 | H6A—N6—H6B | 120.0 |
C23—C22—C19 | 119.9 (2) | S1—O1—Cu1 | 128.28 (10) |
C23—C22—H22 | 120.1 | C31—O5—H5 | 109.5 |
C19—C22—H22 | 120.1 | C38—O10—H10A | 109.5 |
C22—C23—C24 | 119.8 (2) | H1WB—O1W—H1WA | 97.9 |
C22—C23—H23 | 120.1 | O3—S1—O2 | 115.74 (13) |
C24—C23—H23 | 120.1 | O3—S1—O1 | 110.84 (12) |
N4—C24—C23 | 121.8 (2) | O2—S1—O1 | 110.26 (12) |
N4—C24—H24 | 119.1 | O3—S1—C28 | 107.61 (11) |
C23—C24—H24 | 119.1 | O2—S1—C28 | 106.97 (11) |
C30—C25—C26 | 119.3 (2) | O1—S1—C28 | 104.71 (10) |
C30—C25—C31 | 120.1 (2) | O7—S2—O6 | 114.16 (14) |
C26—C25—C31 | 120.6 (2) | O7—S2—O8 | 112.90 (13) |
N5—C26—C27 | 118.2 (2) | O6—S2—O8 | 111.74 (13) |
N5—C26—C25 | 123.9 (2) | O7—S2—C35 | 107.36 (12) |
C27—C26—C25 | 117.9 (2) | O6—S2—C35 | 103.72 (10) |
C28—C27—C26 | 121.1 (2) | O8—S2—C35 | 106.09 (11) |
| | | |
N1—C1—C2—C3 | 1.0 (4) | C37—C32—C38—O9 | −172.9 (3) |
C1—C2—C3—C4 | 0.9 (5) | C33—C32—C38—O9 | 8.6 (4) |
C2—C3—C4—C5 | −2.2 (4) | C37—C32—C38—O10 | 8.8 (3) |
C2—C3—C4—C9 | 176.7 (3) | C33—C32—C38—O10 | −169.7 (2) |
C3—C4—C5—N1 | 1.8 (4) | C2—C1—N1—C5 | −1.5 (4) |
C9—C4—C5—N1 | −177.2 (2) | C2—C1—N1—Cu1 | 172.4 (2) |
C3—C4—C5—C6 | −178.7 (2) | C4—C5—N1—C1 | 0.1 (4) |
C9—C4—C5—C6 | 2.3 (4) | C6—C5—N1—C1 | −179.5 (2) |
N1—C5—C6—N2 | −3.6 (3) | C4—C5—N1—Cu1 | −175.1 (2) |
C4—C5—C6—N2 | 176.9 (2) | C6—C5—N1—Cu1 | 5.4 (3) |
N1—C5—C6—C7 | 175.1 (2) | N2—Cu1—N1—C1 | −178.5 (2) |
C4—C5—C6—C7 | −4.4 (4) | N4—Cu1—N1—C1 | 0.7 (2) |
N2—C6—C7—C10 | 2.9 (4) | N3—Cu1—N1—C1 | −85.4 (2) |
C5—C6—C7—C10 | −175.7 (2) | O1—Cu1—N1—C1 | 94.9 (2) |
N2—C6—C7—C8 | −177.7 (2) | N2—Cu1—N1—C5 | −4.30 (16) |
C5—C6—C7—C8 | 3.6 (4) | N4—Cu1—N1—C5 | 174.95 (16) |
C10—C7—C8—C9 | 178.4 (3) | N3—Cu1—N1—C5 | 88.83 (16) |
C6—C7—C8—C9 | −0.9 (5) | O1—Cu1—N1—C5 | −90.88 (16) |
C7—C8—C9—C4 | −1.2 (5) | C11—C12—N2—C6 | 0.0 (4) |
C3—C4—C9—C8 | −178.4 (3) | C11—C12—N2—Cu1 | 176.7 (2) |
C5—C4—C9—C8 | 0.4 (5) | C7—C6—N2—C12 | −1.9 (4) |
C6—C7—C10—C11 | −2.1 (4) | C5—C6—N2—C12 | 176.8 (2) |
C8—C7—C10—C11 | 178.6 (3) | C7—C6—N2—Cu1 | −179.06 (19) |
C7—C10—C11—C12 | 0.3 (5) | C5—C6—N2—Cu1 | −0.4 (3) |
C10—C11—C12—N2 | 0.8 (5) | N4—Cu1—N2—C12 | 51 (5) |
N3—C13—C14—C15 | −0.4 (4) | N3—Cu1—N2—C12 | 66.0 (3) |
C13—C14—C15—C16 | 0.3 (4) | N1—Cu1—N2—C12 | −174.3 (3) |
C14—C15—C16—C17 | −0.7 (4) | O1—Cu1—N2—C12 | −60.2 (2) |
C14—C15—C16—C21 | −179.8 (3) | N4—Cu1—N2—C6 | −133 (5) |
C15—C16—C17—N3 | 1.1 (4) | N3—Cu1—N2—C6 | −117.17 (17) |
C21—C16—C17—N3 | −179.6 (2) | N1—Cu1—N2—C6 | 2.55 (17) |
C15—C16—C17—C18 | −178.8 (2) | O1—Cu1—N2—C6 | 116.70 (17) |
C21—C16—C17—C18 | 0.4 (4) | C14—C13—N3—C17 | 0.9 (4) |
N3—C17—C18—N4 | −0.5 (3) | C14—C13—N3—Cu1 | 179.6 (2) |
C16—C17—C18—N4 | 179.5 (2) | C16—C17—N3—C13 | −1.2 (3) |
N3—C17—C18—C19 | 178.6 (2) | C18—C17—N3—C13 | 178.7 (2) |
C16—C17—C18—C19 | −1.4 (3) | C16—C17—N3—Cu1 | 179.77 (19) |
N4—C18—C19—C22 | 1.2 (3) | C18—C17—N3—Cu1 | −0.2 (3) |
C17—C18—C19—C22 | −177.8 (2) | N2—Cu1—N3—C13 | 2.1 (2) |
N4—C18—C19—C20 | −179.0 (2) | N4—Cu1—N3—C13 | −178.2 (2) |
C17—C18—C19—C20 | 2.0 (3) | N1—Cu1—N3—C13 | −82.4 (2) |
C18—C19—C20—C21 | −1.6 (4) | O1—Cu1—N3—C13 | 97.3 (2) |
C22—C19—C20—C21 | 178.1 (3) | N2—Cu1—N3—C17 | −179.15 (16) |
C19—C20—C21—C16 | 0.6 (4) | N4—Cu1—N3—C17 | 0.57 (16) |
C17—C16—C21—C20 | 0.0 (4) | N1—Cu1—N3—C17 | 96.40 (17) |
C15—C16—C21—C20 | 179.2 (3) | O1—Cu1—N3—C17 | −83.93 (17) |
C18—C19—C22—C23 | 0.5 (4) | C23—C24—N4—C18 | 1.6 (4) |
C20—C19—C22—C23 | −179.3 (2) | C23—C24—N4—Cu1 | 176.73 (19) |
C19—C22—C23—C24 | −1.1 (4) | C19—C18—N4—C24 | −2.3 (3) |
C22—C23—C24—N4 | 0.1 (4) | C17—C18—N4—C24 | 176.7 (2) |
C30—C25—C26—N5 | −179.5 (2) | C19—C18—N4—Cu1 | −178.07 (18) |
C31—C25—C26—N5 | 1.5 (4) | C17—C18—N4—Cu1 | 0.9 (3) |
C30—C25—C26—C27 | 0.1 (3) | N2—Cu1—N4—C24 | −161 (5) |
C31—C25—C26—C27 | −178.9 (2) | N3—Cu1—N4—C24 | −176.2 (2) |
N5—C26—C27—C28 | 179.5 (2) | N1—Cu1—N4—C24 | 64.2 (2) |
C25—C26—C27—C28 | −0.1 (3) | O1—Cu1—N4—C24 | −50.0 (2) |
C26—C27—C28—C29 | 0.4 (4) | N2—Cu1—N4—C18 | 15 (5) |
C26—C27—C28—S1 | 177.37 (18) | N3—Cu1—N4—C18 | −0.82 (16) |
C27—C28—C29—C30 | −0.7 (4) | N1—Cu1—N4—C18 | −120.40 (16) |
S1—C28—C29—C30 | −177.68 (19) | O1—Cu1—N4—C18 | 125.34 (16) |
C28—C29—C30—C25 | 0.7 (4) | N2—Cu1—O1—S1 | 98.77 (13) |
C26—C25—C30—C29 | −0.5 (4) | N4—Cu1—O1—S1 | −80.25 (13) |
C31—C25—C30—C29 | 178.6 (2) | N3—Cu1—O1—S1 | 0.20 (17) |
C30—C25—C31—O4 | −174.4 (2) | N1—Cu1—O1—S1 | 179.89 (12) |
C26—C25—C31—O4 | 4.6 (4) | Cu1—O1—S1—O3 | −158.05 (12) |
C30—C25—C31—O5 | 5.4 (3) | Cu1—O1—S1—O2 | −28.56 (16) |
C26—C25—C31—O5 | −175.5 (2) | Cu1—O1—S1—C28 | 86.18 (14) |
C37—C32—C33—N6 | −177.5 (2) | C27—C28—S1—O3 | 133.2 (2) |
C38—C32—C33—N6 | 1.0 (4) | C29—C28—S1—O3 | −49.7 (2) |
C37—C32—C33—C34 | 1.8 (3) | C27—C28—S1—O2 | 8.2 (2) |
C38—C32—C33—C34 | −179.7 (2) | C29—C28—S1—O2 | −174.7 (2) |
N6—C33—C34—C35 | 178.5 (2) | C27—C28—S1—O1 | −108.8 (2) |
C32—C33—C34—C35 | −0.8 (4) | C29—C28—S1—O1 | 68.3 (2) |
C33—C34—C35—C36 | −0.7 (4) | C34—C35—S2—O7 | 137.1 (2) |
C33—C34—C35—S2 | 173.92 (18) | C36—C35—S2—O7 | −48.1 (2) |
C34—C35—C36—C37 | 1.2 (4) | C34—C35—S2—O6 | −101.7 (2) |
S2—C35—C36—C37 | −173.51 (19) | C36—C35—S2—O6 | 73.1 (2) |
C35—C36—C37—C32 | −0.1 (4) | C34—C35—S2—O8 | 16.2 (2) |
C33—C32—C37—C36 | −1.3 (4) | C36—C35—S2—O8 | −169.1 (2) |
C38—C32—C37—C36 | −179.8 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···O6 | 0.86 | 2.28 | 3.109 (3) | 162 |
N5—H5B···O4 | 0.86 | 2.08 | 2.703 (3) | 129 |
N6—H6A···O1i | 0.86 | 2.64 | 3.207 (3) | 125 |
N6—H6A···O3i | 0.86 | 2.51 | 3.365 (3) | 173 |
N6—H6B···O9 | 0.86 | 2.03 | 2.664 (3) | 130 |
O5—H5···O8ii | 0.82 | 1.84 | 2.651 (2) | 168 |
O10—H10A···O1Wiii | 0.82 | 1.81 | 2.631 (3) | 179 |
O1W—H1WB···O6 | 0.82 | 2.06 | 2.858 (3) | 164 |
O1W—H1WA···O2 | 0.93 | 1.91 | 2.832 (3) | 171 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+2; (iii) −x+1, y+1/2, −z+3/2. |
(zl10)
catena-Poly[[diaquacopper(II)]-µ-3-amino-4-carboxylatobenzene-1-sulfonato-
κ2O4:
O4']
top
Crystal data top
[Cu(C7H6N2O5S)(H2O)2] | F(000) = 636 |
Mr = 314.77 | Dx = 1.977 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 9991 reflections |
a = 8.4858 (9) Å | θ = 2.6–27.6° |
b = 9.9337 (11) Å | µ = 2.29 mm−1 |
c = 14.5512 (13) Å | T = 296 K |
β = 120.445 (5)° | Massive, green |
V = 1057.47 (19) Å3 | 0.3 × 0.28 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 2426 independent reflections |
Radiation source: fine-focus sealed tube | 2186 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
phi and ω scans | θmax = 27.6°, θmin = 2.6° |
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2003) | h = −11→10 |
Tmin = 0.509, Tmax = 0.633 | k = −12→10 |
15782 measured reflections | l = −18→18 |
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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0322P)2 + 0.8556P] where P = (Fo2 + 2Fc2)/3 |
2426 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.43 e Å−3 |
7 restraints | Δρmin = −0.41 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 | |
O1W | 1.0617 (6) | 0.4088 (5) | 0.4517 (4) | 0.0366 (10) | |
H1WA | 1.0097 | 0.3220 | 0.4247 | 0.055* | |
H1WB | 1.1792 | 0.3901 | 0.5078 | 0.055* | |
C1 | 0.8046 (7) | 0.3927 (5) | 0.0753 (4) | 0.0217 (11) | |
C2 | 0.7667 (7) | 0.5176 (5) | 0.1044 (4) | 0.0185 (10) | |
C3 | 0.6913 (7) | 0.6207 (5) | 0.0300 (4) | 0.0206 (10) | |
H3 | 0.6647 | 0.7035 | 0.0489 | 0.031* | |
C4 | 0.6561 (7) | 0.5987 (5) | −0.0728 (4) | 0.0221 (11) | |
C5 | 0.6891 (10) | 0.4745 (6) | −0.1033 (5) | 0.0320 (14) | |
H5 | 0.6628 | 0.4607 | −0.1728 | 0.048* | |
C6 | 0.7609 (9) | 0.3717 (6) | −0.0298 (5) | 0.0314 (13) | |
H6 | 0.7804 | 0.2877 | −0.0504 | 0.047* | |
C7 | 0.8958 (7) | 0.2816 (5) | 0.1548 (4) | 0.0195 (10) | |
Cu1 | 1.06908 (9) | 0.49189 (6) | 0.31066 (5) | 0.0201 (2) | |
N1 | 0.8075 (6) | 0.5373 (4) | 0.2122 (3) | 0.0198 (9) | |
H1A | 0.7357 | 0.4841 | 0.2256 | 0.030* | |
H1B | 0.7863 | 0.6235 | 0.2218 | 0.030* | |
O1 | 1.0102 (5) | 0.3090 (4) | 0.2503 (3) | 0.0221 (8) | |
O2 | 0.8535 (6) | 0.1641 (4) | 0.1185 (3) | 0.0271 (9) | |
O3 | 0.6608 (6) | 0.7278 (4) | −0.2253 (4) | 0.0341 (10) | |
O4 | 0.3681 (6) | 0.6927 (5) | −0.2396 (4) | 0.0388 (11) | |
O5 | 0.5817 (6) | 0.8532 (4) | −0.1127 (3) | 0.0337 (10) | |
O2W | 1.3303 (5) | 0.4500 (4) | 0.3643 (4) | 0.0295 (9) | |
H2WB | 1.3849 | 0.5234 | 0.3687 | 0.044* | |
H2WA | 1.3332 | 0.4002 | 0.3173 | 0.044* | |
S1 | 0.55818 (18) | 0.72806 (13) | −0.17057 (10) | 0.0209 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1W | 0.046 (3) | 0.035 (2) | 0.036 (2) | 0.007 (2) | 0.026 (2) | 0.0070 (19) |
C1 | 0.027 (3) | 0.014 (2) | 0.021 (3) | 0.000 (2) | 0.010 (2) | 0.0003 (19) |
C2 | 0.018 (2) | 0.016 (2) | 0.020 (2) | −0.0016 (18) | 0.008 (2) | −0.0006 (18) |
C3 | 0.023 (3) | 0.014 (2) | 0.025 (3) | 0.0012 (19) | 0.013 (2) | 0.0006 (19) |
C4 | 0.027 (3) | 0.017 (2) | 0.021 (3) | 0.002 (2) | 0.011 (2) | 0.004 (2) |
C5 | 0.050 (4) | 0.022 (3) | 0.022 (3) | 0.006 (3) | 0.017 (3) | 0.000 (2) |
C6 | 0.050 (4) | 0.016 (2) | 0.025 (3) | 0.006 (2) | 0.016 (3) | −0.001 (2) |
C7 | 0.023 (3) | 0.013 (2) | 0.023 (2) | 0.0010 (19) | 0.012 (2) | 0.0006 (19) |
Cu1 | 0.0224 (4) | 0.0125 (3) | 0.0206 (4) | −0.0004 (2) | 0.0073 (3) | −0.0022 (2) |
N1 | 0.024 (2) | 0.0149 (19) | 0.021 (2) | 0.0007 (17) | 0.0118 (19) | −0.0011 (17) |
O1 | 0.0244 (19) | 0.0138 (16) | 0.0209 (18) | 0.0012 (14) | 0.0062 (16) | −0.0014 (14) |
O2 | 0.035 (2) | 0.0120 (17) | 0.0229 (19) | 0.0015 (15) | 0.0063 (17) | 0.0006 (14) |
O3 | 0.049 (3) | 0.025 (2) | 0.045 (3) | 0.0028 (18) | 0.036 (2) | 0.0058 (18) |
O4 | 0.028 (2) | 0.040 (3) | 0.036 (2) | −0.0040 (19) | 0.007 (2) | 0.016 (2) |
O5 | 0.046 (3) | 0.020 (2) | 0.033 (2) | 0.0098 (18) | 0.019 (2) | 0.0024 (17) |
O2W | 0.027 (2) | 0.024 (2) | 0.039 (2) | −0.0049 (16) | 0.0181 (19) | −0.0063 (17) |
S1 | 0.0253 (7) | 0.0163 (6) | 0.0225 (6) | 0.0019 (5) | 0.0129 (6) | 0.0042 (5) |
Geometric parameters (Å, º) top
O1W—Cu1 | 2.243 (4) | C7—O2 | 1.256 (6) |
O1W—H1WA | 0.9577 | C7—O1 | 1.258 (7) |
O1W—H1WB | 0.9324 | Cu1—O2i | 1.932 (4) |
C1—C6 | 1.395 (8) | Cu1—O1 | 1.969 (4) |
C1—C2 | 1.399 (7) | Cu1—O2W | 1.985 (4) |
C1—C7 | 1.498 (7) | Cu1—N1 | 1.990 (4) |
C2—C3 | 1.389 (7) | N1—H1A | 0.9000 |
C2—N1 | 1.439 (7) | N1—H1B | 0.9000 |
C3—C4 | 1.386 (7) | O2—Cu1ii | 1.932 (4) |
C3—H3 | 0.9300 | O3—S1 | 1.448 (4) |
C4—C5 | 1.386 (8) | O4—S1 | 1.447 (5) |
C4—S1 | 1.780 (5) | O5—S1 | 1.457 (4) |
C5—C6 | 1.377 (8) | O2W—H2WB | 0.8491 |
C5—H5 | 0.9300 | O2W—H2WA | 0.8554 |
C6—H6 | 0.9300 | | |
| | | |
Cu1—O1W—H1WA | 100.1 | O2i—Cu1—O1W | 89.85 (17) |
Cu1—O1W—H1WB | 111.2 | O2W—Cu1—O1W | 96.09 (18) |
H1WA—O1W—H1WB | 104.3 | O2i—Cu1—O1 | 174.62 (16) |
C6—C1—C2 | 119.3 (5) | O1—Cu1—N1 | 87.11 (17) |
C6—C1—C7 | 118.8 (5) | O2W—Cu1—N1 | 161.16 (18) |
C2—C1—C7 | 121.8 (5) | O1—Cu1—O1W | 87.13 (17) |
C3—C2—C1 | 120.3 (5) | N1—Cu1—O1W | 101.78 (18) |
C3—C2—N1 | 120.7 (4) | O2i—Cu1—O2W | 88.03 (17) |
C1—C2—N1 | 119.0 (5) | C2—N1—Cu1 | 108.6 (3) |
C4—C3—C2 | 119.1 (5) | C2—N1—H1A | 110.0 |
C4—C3—H3 | 120.4 | Cu1—N1—H1A | 110.0 |
C2—C3—H3 | 120.4 | C2—N1—H1B | 110.0 |
C5—C4—C3 | 121.2 (5) | Cu1—N1—H1B | 110.0 |
C5—C4—S1 | 118.4 (4) | H1A—N1—H1B | 108.4 |
C3—C4—S1 | 120.4 (4) | C7—O1—Cu1 | 124.9 (3) |
C6—C5—C4 | 119.5 (5) | C7—O2—Cu1ii | 130.7 (4) |
C6—C5—H5 | 120.2 | Cu1—O2W—H2WB | 107.9 |
C4—C5—H5 | 120.2 | Cu1—O2W—H2WA | 106.6 |
C5—C6—C1 | 120.5 (5) | H2WB—O2W—H2WA | 108.7 |
C5—C6—H6 | 119.7 | O4—S1—O3 | 112.8 (3) |
C1—C6—H6 | 119.7 | O4—S1—O5 | 112.7 (3) |
O2—C7—O1 | 124.1 (5) | O3—S1—O5 | 112.0 (3) |
O2—C7—C1 | 115.8 (5) | O4—S1—C4 | 106.5 (3) |
O1—C7—C1 | 120.1 (4) | O3—S1—C4 | 105.7 (3) |
O1—Cu1—O2W | 87.87 (17) | O5—S1—C4 | 106.4 (2) |
O2i—Cu1—N1 | 97.87 (17) | | |
| | | |
C6—C1—C2—C3 | −1.9 (8) | O2i—Cu1—N1—C2 | 121.3 (3) |
C7—C1—C2—C3 | 176.4 (5) | O1—Cu1—N1—C2 | −60.8 (3) |
C6—C1—C2—N1 | 178.3 (5) | O2W—Cu1—N1—C2 | 14.0 (7) |
C7—C1—C2—N1 | −3.4 (8) | O1W—Cu1—N1—C2 | −147.2 (3) |
C1—C2—C3—C4 | −0.7 (8) | O2—C7—O1—Cu1 | −176.6 (4) |
N1—C2—C3—C4 | 179.1 (5) | C1—C7—O1—Cu1 | 5.3 (7) |
C2—C3—C4—C5 | 2.3 (9) | O2i—Cu1—O1—C7 | −167.3 (17) |
C2—C3—C4—S1 | 179.6 (4) | O2W—Cu1—O1—C7 | −127.0 (4) |
C3—C4—C5—C6 | −1.1 (10) | N1—Cu1—O1—C7 | 34.9 (4) |
S1—C4—C5—C6 | −178.5 (5) | O1W—Cu1—O1—C7 | 136.8 (4) |
C4—C5—C6—C1 | −1.5 (10) | O1—C7—O2—Cu1ii | 3.0 (9) |
C2—C1—C6—C5 | 3.0 (9) | C1—C7—O2—Cu1ii | −178.8 (4) |
C7—C1—C6—C5 | −175.3 (6) | C5—C4—S1—O4 | 73.5 (6) |
C6—C1—C7—O2 | −32.0 (8) | C3—C4—S1—O4 | −103.9 (5) |
C2—C1—C7—O2 | 149.7 (5) | C5—C4—S1—O3 | −46.7 (6) |
C6—C1—C7—O1 | 146.3 (6) | C3—C4—S1—O3 | 135.9 (5) |
C2—C1—C7—O1 | −32.0 (8) | C5—C4—S1—O5 | −166.0 (5) |
C3—C2—N1—Cu1 | −125.3 (4) | C3—C4—S1—O5 | 16.6 (5) |
C1—C2—N1—Cu1 | 54.5 (5) | | |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WB···O5ii | 0.93 | 1.86 | 2.786 (7) | 176 |
N1—H1A···O4iii | 0.90 | 2.02 | 2.864 (6) | 156 |
N1—H1B···O3iv | 0.90 | 2.18 | 2.995 (6) | 151 |
O2W—H2WB···O5v | 0.85 | 1.98 | 2.786 (6) | 159 |
O2W—H2WA···O3vi | 0.86 | 1.86 | 2.715 (6) | 172 |
Symmetry codes: (ii) −x+2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z; (iv) x, −y+3/2, z+1/2; (v) x+1, −y+3/2, z+1/2; (vi) −x+2, −y+1, −z. |