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The assembly of CuII with the multifunctional ligand 2-amino-4-sulfo­benzoic acid (H2asba) in the presence of the auxiliary flexible ligands 1,4-bis­(triazol-1-ylmeth­yl)benzene (bbtz) and 1,4-bis­(imidazol-1-ylmeth­yl)benzene (bix) under ambient conditions resulted in two new supra­molecular coordination polymers, namely poly[[(3-amino-4-carb­oxy­benzene­sulfonato-κO)aqua­bis­[μ2-1,4-bis­(tri­az­ol-1-ylmeth­yl)benzene-κ2N4:N4′]copper(II)] 3-amino-4-carb­oxy­benzene­sul­fon­ate tetrahydrate], {[Cu(C7H6NO5S)(C12H12N6)2(H2O)](C7H6NO5S)·4H2O}n, (1), and poly[[bis­(μ2-2-amino-4-sulfon­ato­benzoato-κ3O1:N,O1′)tetra­aqua­[μ2-1,4-bis­(triazol-1-ylmeth­yl)benzene-κ2N4:N4′]dicopper(II)] tetra­hydrate], {[Cu2(C7H5NO5S)2(C14H14N4)(H2O)4]·4H2O}n, (2). Single-crystal X-ray structure diffraction analysis of (1) reveals that the bbtz ligand acts as a bridge, linking adjacent CuII ions into a two-dimensional cationic (4,4) topological network, in which the coordinated 3-amino-4-carb­oxy­benzene­sulfonate (Hasba) anion uses its sulfonate group to bind with the CuII ion in a monodentate fashion and the carboxyl­ate group remains protonated. The lattice Hasba anion resides in the two-dimensional layer and balances the charge. The carboxyl­ate group of the 2-amino-4-sulfon­ato­benzoate (asba2−) ligand in (2) is involved in bidentate coordination, connecting adjacent CuII ions into carboxyl­ate-bridged chains which are further bridged by the auxiliary flexible bix ligand in a transgauche (TG) mode, resulting in the formation of a two-dimensional network architecture. The amino group of the asba2− ligand in (2) also takes part in the coordination with the central CuII ion. The six-coordinated CuII centres in (1) and (2) exhibit distorted octa­hedral coordination geometries. Extensive hydrogen bonding exists in both (1) and (2). The inter­layer hydrogen bonds in both compounds further extend adjacent two-dimensional layers into three-dimensional supra­molecular network architectures. Furthermore, a detailed analysis of the solid-state UV–Vis–NIR (NIR is near IR) diffuse reflectance data indicates that (1) and (2) may have potential as wide band gap indirect semiconductor materials. Compounds (1) and (2) show reversible and irreversible dehydration–rehydration behaviours, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617014899/ky3127sup1.cif
Contains datablocks 1, 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014899/ky31271sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014899/ky31272sup3.hkl
Contains datablock 2

CCDC references: 1579933; 1579932

Computing details top

For both structures, data collection: SMART (Bruker, 2002); cell refinement: SMART (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008). Software used to prepare material for publication: SHELXTL for (1); SHELXTL (Sheldrick, 2008) for (2).

Poly[[(3-amino-4-carboxybenzenesulfonato-κO)aquabis[µ2-1,4-bis(triazol-1-ylmethyl)benzene-κ2N4:N4']copper(II)] 3-amino-4-carboxybenzenesulfonate 3.5-hydrate] (1) top
Crystal data top
[Cu(C7H6NO5S)(C12H12N6)2(H2O)](C7H6NO5S)·4H2OF(000) = 2211
Mr = 1066.58Dx = 1.534 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 9905 reflections
a = 24.390 (3) Åθ = 2.3–26.1°
b = 11.8710 (15) ŵ = 0.65 mm1
c = 16.048 (2) ÅT = 296 K
β = 96.325 (4)°Block, green
V = 4618.2 (10) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
10691 independent reflections
Radiation source: fine-focus sealed tube7337 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
phi and ω scansθmax = 27.7°, θmin = 0.8°
Absorption correction: empirical (using intensity measurements)
(SADABS; Bruker, 2002)
h = 3129
Tmin = 0.824, Tmax = 0.879k = 1513
71401 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0891P)2 + 5.1487P]
where P = (Fo2 + 2Fc2)/3
10691 reflections(Δ/σ)max = 0.001
631 parametersΔρmax = 1.68 e Å3
22 restraintsΔρmin = 0.96 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
C10.34850 (13)0.6619 (3)0.3632 (2)0.0397 (8)
H10.33510.59120.34630.048*
C20.35841 (15)0.8351 (3)0.3822 (3)0.0476 (9)
H20.35160.91220.37980.057*
C30.43344 (15)0.5983 (4)0.4532 (3)0.0547 (11)
H3A0.42080.52270.43840.066*
H3B0.43430.60620.51350.066*
C40.49113 (14)0.6137 (3)0.4289 (2)0.0422 (9)
C50.52669 (16)0.6902 (4)0.4715 (2)0.0493 (10)
H50.51440.73460.51350.059*
C60.57999 (16)0.7013 (3)0.4524 (3)0.0495 (10)
H60.60360.75240.48200.059*
C70.59880 (15)0.6369 (3)0.3893 (2)0.0403 (8)
C80.56272 (16)0.5609 (3)0.3464 (2)0.0434 (8)
H80.57470.51680.30400.052*
C90.50955 (15)0.5502 (3)0.3659 (2)0.0437 (9)
H90.48580.49950.33620.052*
C100.65675 (16)0.6515 (3)0.3667 (3)0.0535 (11)
H10A0.65570.69370.31480.064*
H10B0.67810.69440.41030.064*
C110.28567 (16)0.8841 (4)0.1117 (2)0.0480 (9)
H110.27440.81980.08150.058*
C120.30100 (14)0.9971 (3)0.2124 (2)0.0416 (8)
H120.30361.03160.26470.050*
C130.15408 (17)0.6936 (4)0.1511 (3)0.0567 (11)
H130.16470.61870.15820.068*
C140.15330 (13)0.8690 (3)0.1636 (2)0.0410 (8)
H140.16180.94290.17930.049*
C150.07192 (15)0.9111 (4)0.0598 (3)0.0563 (12)
H15A0.07380.89440.00110.068*
H15B0.08300.98890.06920.068*
C160.01313 (13)0.8986 (3)0.0782 (2)0.0392 (8)
C170.02157 (15)0.8195 (3)0.0358 (2)0.0456 (9)
H170.00720.76720.00090.055*
C180.07692 (15)0.8181 (3)0.0452 (2)0.0409 (8)
H180.09970.76520.01600.049*
C190.09926 (13)0.8943 (3)0.09744 (19)0.0304 (7)
C200.06445 (14)0.9691 (3)0.1424 (2)0.0386 (8)
H200.07831.01850.17990.046*
C210.00888 (15)0.9710 (3)0.1318 (2)0.0427 (9)
H210.01411.02280.16190.051*
C220.16053 (14)0.8951 (3)0.1009 (2)0.0397 (8)
H22A0.17870.86330.04940.048*
H22B0.16930.84790.14700.048*
C230.19680 (16)0.6778 (4)0.4132 (2)0.0471 (9)
H230.19790.74820.43880.057*
C240.20780 (13)0.5495 (3)0.3266 (2)0.0362 (8)
H240.21750.50840.28110.043*
C250.49396 (15)0.6618 (3)0.1623 (2)0.0448 (9)
C260.47822 (17)0.5551 (4)0.1322 (3)0.0578 (11)
C270.42161 (17)0.5280 (4)0.1207 (3)0.0576 (11)
H270.41060.45720.10050.069*
C280.38286 (15)0.6040 (3)0.1386 (2)0.0411 (8)
C290.39860 (16)0.7091 (3)0.1713 (3)0.0498 (10)
H290.37220.76030.18520.060*
C300.45393 (16)0.7363 (3)0.1828 (3)0.0491 (9)
H300.46460.80640.20480.059*
C310.55234 (16)0.6973 (4)0.1728 (3)0.0518 (10)
C320.00522 (18)0.3657 (4)0.1592 (2)0.0517 (10)
C330.01680 (19)0.2702 (4)0.2103 (2)0.0514 (10)
C340.07041 (19)0.2273 (4)0.2196 (3)0.0528 (10)
H340.07840.16390.25280.063*
C350.11131 (18)0.2767 (4)0.1806 (3)0.0522 (10)
C360.1008 (2)0.3729 (4)0.1319 (3)0.0591 (11)
H360.12900.40760.10670.071*
C370.0482 (2)0.4156 (4)0.1216 (3)0.0588 (11)
H370.04100.47940.08860.071*
C380.0507 (2)0.4146 (4)0.1472 (3)0.0644 (12)
Cu10.251700 (15)0.77554 (4)0.26931 (3)0.03449 (14)
N10.32407 (11)0.7587 (2)0.34161 (18)0.0349 (6)
N20.40203 (14)0.7917 (3)0.4251 (2)0.0534 (9)
N30.39442 (11)0.6801 (3)0.41188 (19)0.0407 (7)
N40.68359 (12)0.5430 (3)0.3567 (2)0.0438 (7)
N50.69315 (14)0.4715 (3)0.4225 (2)0.0523 (8)
N60.28142 (11)0.8948 (2)0.19525 (18)0.0378 (7)
N70.18184 (11)0.7794 (2)0.1918 (2)0.0395 (7)
N80.11029 (14)0.7255 (3)0.1001 (3)0.0599 (10)
N90.11124 (11)0.8385 (3)0.11044 (19)0.0409 (7)
N100.18163 (11)1.0086 (2)0.11203 (17)0.0355 (6)
N110.17480 (14)1.0901 (3)0.0555 (2)0.0498 (8)
N120.21812 (11)0.6580 (3)0.34008 (18)0.0367 (7)
N130.51525 (19)0.4748 (4)0.1169 (4)0.117 (2)
H13A0.55000.48880.12590.140*
H13B0.50410.40980.09860.140*
N140.02227 (18)0.2169 (3)0.2508 (3)0.0676 (11)
H14A0.01360.15830.28090.081*
H14B0.05560.24180.24620.081*
O10.28553 (11)0.6187 (3)0.18669 (17)0.0522 (7)
O20.29177 (13)0.6153 (3)0.03856 (18)0.0695 (9)
O30.31002 (13)0.4468 (3)0.1216 (2)0.0697 (9)
O40.59033 (12)0.6377 (3)0.1552 (2)0.0741 (10)
O50.56022 (12)0.8002 (3)0.2012 (2)0.0686 (9)
H5A0.59310.81590.20340.103*
O60.18671 (16)0.1733 (4)0.1099 (2)0.0871 (11)
O70.17869 (17)0.1274 (4)0.2520 (3)0.0951 (12)
O80.21547 (14)0.3067 (3)0.2196 (2)0.0790 (10)
O90.05383 (17)0.5075 (4)0.1018 (3)0.0955 (12)
H9A0.08600.52850.09420.143*
O100.09021 (16)0.3757 (4)0.1768 (3)0.0929 (12)
O1W0.23600 (15)0.9190 (3)0.3691 (2)0.0744 (10)
H1WA0.20870.93410.33240.089*
H1WB0.23980.97180.40520.089*
O2W0.34047 (14)0.3855 (3)0.2955 (2)0.0794 (10)
H2WB0.32020.35460.32850.095*
H2WA0.32310.39210.24670.095*
O3W0.23778 (15)0.3237 (3)0.0142 (2)0.0838 (11)
H3WB0.26050.37110.03880.101*
H3WA0.22380.28480.05130.101*
O4W0.15546 (16)0.0847 (4)0.4082 (3)0.0989 (13)
H4WA0.15920.11050.35910.119*
H4WB0.18240.10920.44240.119*
O5W0.2872 (4)0.1836 (7)0.3720 (6)0.258 (4)
H5WA0.31730.17800.34830.309*
H5WB0.29600.17060.42480.309*
S10.31176 (4)0.56852 (9)0.11942 (6)0.0449 (2)
S20.17878 (5)0.21731 (10)0.19082 (7)0.0605 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0260 (17)0.041 (2)0.051 (2)0.0019 (14)0.0009 (15)0.0062 (16)
C20.0355 (19)0.040 (2)0.065 (3)0.0002 (16)0.0043 (18)0.0001 (18)
C30.035 (2)0.065 (3)0.063 (3)0.0107 (18)0.0024 (18)0.029 (2)
C40.0336 (18)0.049 (2)0.043 (2)0.0103 (16)0.0018 (15)0.0143 (17)
C50.038 (2)0.064 (3)0.046 (2)0.0133 (18)0.0039 (17)0.0117 (19)
C60.037 (2)0.049 (2)0.060 (2)0.0070 (17)0.0030 (18)0.0164 (19)
C70.0363 (19)0.0318 (18)0.053 (2)0.0046 (14)0.0056 (16)0.0035 (16)
C80.047 (2)0.039 (2)0.046 (2)0.0029 (16)0.0076 (17)0.0032 (16)
C90.039 (2)0.042 (2)0.048 (2)0.0037 (16)0.0036 (16)0.0044 (17)
C100.045 (2)0.033 (2)0.086 (3)0.0006 (16)0.019 (2)0.011 (2)
C110.043 (2)0.049 (2)0.051 (2)0.0144 (17)0.0003 (17)0.0061 (18)
C120.0330 (18)0.039 (2)0.053 (2)0.0027 (15)0.0072 (16)0.0044 (17)
C130.041 (2)0.044 (2)0.082 (3)0.0048 (18)0.011 (2)0.008 (2)
C140.0247 (16)0.042 (2)0.056 (2)0.0026 (15)0.0028 (15)0.0124 (17)
C150.0311 (19)0.077 (3)0.061 (3)0.0105 (19)0.0026 (17)0.038 (2)
C160.0267 (17)0.051 (2)0.0390 (19)0.0089 (15)0.0007 (14)0.0194 (16)
C170.039 (2)0.055 (2)0.044 (2)0.0139 (18)0.0102 (16)0.0048 (18)
C180.0370 (19)0.041 (2)0.044 (2)0.0019 (16)0.0033 (15)0.0085 (16)
C190.0301 (16)0.0311 (17)0.0301 (16)0.0053 (13)0.0026 (13)0.0050 (13)
C200.0384 (19)0.042 (2)0.0342 (18)0.0039 (15)0.0003 (15)0.0039 (15)
C210.0355 (19)0.049 (2)0.040 (2)0.0028 (16)0.0088 (15)0.0064 (17)
C220.0363 (19)0.0388 (19)0.045 (2)0.0011 (15)0.0105 (15)0.0066 (16)
C230.051 (2)0.049 (2)0.043 (2)0.0156 (18)0.0130 (17)0.0068 (18)
C240.0292 (17)0.043 (2)0.0376 (18)0.0020 (15)0.0100 (14)0.0042 (15)
C250.0366 (19)0.049 (2)0.050 (2)0.0029 (16)0.0059 (16)0.0079 (18)
C260.041 (2)0.059 (3)0.074 (3)0.0136 (19)0.006 (2)0.008 (2)
C270.047 (2)0.049 (2)0.076 (3)0.0044 (19)0.005 (2)0.017 (2)
C280.0355 (19)0.045 (2)0.043 (2)0.0000 (16)0.0065 (15)0.0010 (16)
C290.038 (2)0.045 (2)0.067 (3)0.0011 (17)0.0114 (19)0.0024 (19)
C300.039 (2)0.043 (2)0.065 (3)0.0023 (17)0.0074 (18)0.0013 (19)
C310.038 (2)0.057 (3)0.060 (3)0.0059 (19)0.0052 (18)0.017 (2)
C320.063 (3)0.051 (2)0.043 (2)0.006 (2)0.0139 (19)0.0127 (19)
C330.065 (3)0.050 (2)0.041 (2)0.018 (2)0.0173 (19)0.0195 (18)
C340.067 (3)0.047 (2)0.045 (2)0.008 (2)0.006 (2)0.0100 (18)
C350.059 (3)0.049 (2)0.049 (2)0.009 (2)0.0066 (19)0.0161 (19)
C360.065 (3)0.056 (3)0.059 (3)0.014 (2)0.018 (2)0.009 (2)
C370.074 (3)0.054 (3)0.050 (2)0.003 (2)0.012 (2)0.005 (2)
C380.073 (3)0.066 (3)0.057 (3)0.006 (2)0.016 (2)0.009 (2)
Cu10.0198 (2)0.0387 (3)0.0443 (3)0.00073 (16)0.00056 (16)0.01186 (18)
N10.0250 (13)0.0371 (16)0.0424 (16)0.0029 (11)0.0028 (12)0.0033 (13)
N20.0390 (18)0.052 (2)0.066 (2)0.0006 (15)0.0105 (16)0.0015 (17)
N30.0284 (15)0.0474 (18)0.0455 (17)0.0063 (13)0.0005 (13)0.0104 (14)
N40.0333 (16)0.0397 (17)0.059 (2)0.0016 (13)0.0085 (14)0.0102 (15)
N50.0492 (19)0.055 (2)0.052 (2)0.0105 (16)0.0039 (16)0.0108 (17)
N60.0287 (14)0.0404 (17)0.0440 (17)0.0035 (12)0.0027 (12)0.0105 (13)
N70.0259 (14)0.0397 (17)0.0522 (18)0.0005 (12)0.0007 (13)0.0125 (14)
N80.0402 (19)0.062 (2)0.072 (2)0.0022 (16)0.0164 (17)0.0041 (19)
N90.0251 (14)0.0471 (19)0.0503 (18)0.0050 (12)0.0034 (13)0.0161 (14)
N100.0296 (14)0.0401 (16)0.0377 (15)0.0016 (12)0.0081 (12)0.0025 (13)
N110.055 (2)0.055 (2)0.0418 (18)0.0151 (16)0.0161 (15)0.0057 (15)
N120.0266 (14)0.0447 (18)0.0391 (16)0.0030 (12)0.0054 (12)0.0067 (13)
N130.054 (3)0.092 (4)0.203 (6)0.019 (3)0.008 (3)0.067 (4)
N140.079 (3)0.058 (2)0.071 (3)0.014 (2)0.030 (2)0.0065 (19)
O10.0378 (14)0.0645 (18)0.0556 (16)0.0028 (13)0.0113 (12)0.0079 (14)
O20.0578 (19)0.101 (3)0.0478 (17)0.0080 (18)0.0037 (14)0.0024 (17)
O30.0580 (19)0.0498 (18)0.101 (3)0.0112 (15)0.0075 (17)0.0127 (17)
O40.0391 (16)0.081 (2)0.104 (3)0.0074 (16)0.0157 (17)0.008 (2)
O50.0409 (16)0.063 (2)0.099 (3)0.0064 (14)0.0032 (16)0.0110 (18)
O60.083 (3)0.108 (3)0.070 (2)0.015 (2)0.0084 (19)0.034 (2)
O70.085 (3)0.092 (3)0.109 (3)0.010 (2)0.012 (2)0.023 (2)
O80.064 (2)0.083 (2)0.091 (3)0.0171 (18)0.0101 (19)0.030 (2)
O90.077 (3)0.098 (3)0.114 (3)0.015 (2)0.021 (2)0.030 (3)
O100.071 (2)0.112 (3)0.102 (3)0.007 (2)0.035 (2)0.014 (2)
O1W0.087 (2)0.059 (2)0.079 (2)0.0216 (17)0.0191 (19)0.0093 (17)
O2W0.060 (2)0.083 (2)0.094 (3)0.0173 (18)0.0046 (18)0.008 (2)
O3W0.084 (3)0.087 (3)0.075 (2)0.012 (2)0.0109 (19)0.008 (2)
O4W0.070 (2)0.112 (3)0.112 (3)0.002 (2)0.003 (2)0.017 (3)
O5W0.220 (7)0.338 (9)0.224 (7)0.048 (7)0.067 (6)0.003 (7)
S10.0369 (5)0.0504 (6)0.0473 (5)0.0047 (4)0.0049 (4)0.0049 (4)
S20.0609 (7)0.0652 (7)0.0555 (7)0.0041 (5)0.0072 (5)0.0146 (5)
Geometric parameters (Å, º) top
C1—N31.311 (4)C26—C271.410 (6)
C1—N11.322 (4)C27—C281.360 (5)
C1—H10.9300C27—H270.9300
C2—N21.308 (5)C28—C291.391 (5)
C2—N11.353 (5)C28—S11.778 (4)
C2—H20.9300C29—C301.380 (5)
C3—N31.466 (4)C29—H290.9300
C3—C41.512 (5)C30—H300.9300
C3—H3A0.9700C31—O41.224 (5)
C3—H3B0.9700C31—O51.310 (5)
C4—C91.376 (5)C32—C371.399 (6)
C4—C51.384 (6)C32—C331.409 (6)
C5—C61.375 (6)C32—C381.475 (7)
C5—H50.9300C33—N141.366 (5)
C6—C71.387 (5)C33—C341.396 (6)
C6—H60.9300C34—C351.366 (6)
C7—C81.389 (5)C34—H340.9300
C7—C101.507 (5)C35—C361.392 (6)
C8—C91.373 (5)C35—S21.781 (5)
C8—H80.9300C36—C371.373 (7)
C9—H90.9300C36—H360.9300
C10—N41.461 (5)C37—H370.9300
C10—H10A0.9700C38—O101.213 (6)
C10—H10B0.9700C38—O91.320 (6)
C11—N61.362 (5)Cu1—N12.013 (3)
C11—H110.9300Cu1—N62.033 (3)
C12—N61.324 (5)Cu1—N71.997 (3)
C12—N4i1.326 (5)Cu1—N122.028 (3)
C12—H120.9300Cu1—O1W2.397 (3)
C13—N81.327 (5)Cu1—O12.479 (3)
C13—N71.351 (5)C11—N5i1.307 (5)
C13—H130.9300C24—N10ii1.323 (4)
C14—N91.311 (5)N2—N31.352 (5)
C14—N71.323 (4)N4—C12iii1.326 (5)
C14—H140.9300N4—N51.355 (5)
C15—N91.467 (4)N5—C11iii1.307 (5)
C15—C161.503 (5)N8—N91.352 (5)
C15—H15A0.9700N10—C24iv1.323 (4)
C15—H15B0.9700N10—N111.348 (4)
C16—C211.366 (5)N11—C23iv1.298 (5)
C16—C171.391 (5)N13—H13A0.8601
C17—C181.375 (5)N13—H13B0.8600
C17—H170.9300N14—H14A0.8600
C18—C191.385 (5)N14—H14B0.8599
C18—H180.9300O1—S11.443 (3)
C19—C201.377 (5)O2—S11.446 (3)
C19—C221.502 (5)O3—S11.447 (3)
C20—C211.385 (5)O5—H5A0.8200
C20—H200.9300O6—S21.432 (3)
C21—H210.9300O7—S21.450 (4)
C22—N101.461 (4)O8—S21.431 (3)
C22—H22A0.9700O9—H9A0.8200
C22—H22B0.9700O1W—H1WA0.8583
C23—N11ii1.298 (5)O1W—H1WB0.8515
C23—N121.356 (5)O2W—H2WB0.8466
C23—H230.9300O2W—H2WA0.8511
C24—N10ii1.323 (4)O3W—H3WB0.8561
C24—N121.325 (5)O3W—H3WA0.8550
C24—H240.9300O4W—H4WA0.8586
C25—C301.383 (5)O4W—H4WB0.8596
C25—C261.394 (6)O5W—H5WA0.8656
C25—C311.477 (5)O5W—H5WB0.8649
C26—N131.354 (6)
N3—C1—N1110.1 (3)C29—C30—C25121.6 (4)
N3—C1—H1124.9C29—C30—H30119.2
N1—C1—H1124.9C25—C30—H30119.2
N2—C2—N1114.4 (3)O4—C31—O5122.3 (4)
N2—C2—H2122.8O4—C31—C25123.6 (4)
N1—C2—H2122.8O5—C31—C25114.1 (4)
N3—C3—C4112.3 (3)C37—C32—C33118.7 (4)
N3—C3—H3A109.2C37—C32—C38120.2 (4)
C4—C3—H3A109.2C33—C32—C38121.1 (4)
N3—C3—H3B109.2N14—C33—C34118.3 (4)
C4—C3—H3B109.2N14—C33—C32122.9 (4)
H3A—C3—H3B107.9C34—C33—C32118.7 (4)
C9—C4—C5119.1 (3)C35—C34—C33121.2 (4)
C9—C4—C3120.8 (4)C35—C34—H34119.4
C5—C4—C3120.1 (4)C33—C34—H34119.4
C6—C5—C4120.6 (4)C34—C35—C36120.7 (4)
C6—C5—H5119.7C34—C35—S2120.1 (4)
C4—C5—H5119.7C36—C35—S2119.1 (3)
C5—C6—C7120.5 (4)C37—C36—C35118.8 (4)
C5—C6—H6119.7C37—C36—H36120.6
C7—C6—H6119.7C35—C36—H36120.6
C6—C7—C8118.5 (3)C36—C37—C32121.8 (4)
C6—C7—C10120.5 (3)C36—C37—H37119.1
C8—C7—C10121.0 (3)C32—C37—H37119.1
C9—C8—C7120.7 (4)O10—C38—O9122.3 (5)
C9—C8—H8119.7O10—C38—C32124.2 (5)
C7—C8—H8119.7O9—C38—C32113.5 (4)
C8—C9—C4120.6 (4)N7—Cu1—N1174.62 (13)
C8—C9—H9119.7N7—Cu1—N1289.73 (11)
C4—C9—H9119.7N1—Cu1—N1289.50 (11)
N4—C10—C7111.6 (3)N7—Cu1—N687.38 (11)
N4—C10—H10A109.3N1—Cu1—N693.43 (11)
C7—C10—H10A109.3N12—Cu1—N6177.05 (11)
N4—C10—H10B109.3N7—Cu1—O1W102.23 (13)
C7—C10—H10B109.3N1—Cu1—O1W83.11 (12)
H10A—C10—H10B108.0N12—Cu1—O1W90.60 (12)
N5i—C11—N6114.6 (4)N6—Cu1—O1W89.41 (12)
N5i—C11—H11122.7N7—Cu1—O189.75 (11)
N6—C11—H11122.7N1—Cu1—O184.90 (10)
N6—C12—N4i109.4 (3)N12—Cu1—O187.78 (11)
N6—C12—H12125.3N6—Cu1—O192.82 (11)
N4i—C12—H12125.3O1W—Cu1—O1167.91 (11)
N8—C13—N7114.2 (4)C1—N1—C2102.7 (3)
N8—C13—H13122.9C1—N1—Cu1125.4 (2)
N7—C13—H13122.9C2—N1—Cu1131.9 (2)
N9—C14—N7110.2 (3)C2—N2—N3102.4 (3)
N9—C14—H14124.9C1—N3—N2110.4 (3)
N7—C14—H14124.9C1—N3—C3129.1 (3)
N9—C15—C16114.4 (3)N2—N3—C3120.5 (3)
N9—C15—H15A108.7C12iii—N4—N5110.7 (3)
C16—C15—H15A108.7C12iii—N4—C10128.7 (4)
N9—C15—H15B108.7N5—N4—C10120.5 (3)
C16—C15—H15B108.7C11iii—N5—N4102.3 (3)
H15A—C15—H15B107.6C12—N6—C11103.0 (3)
C21—C16—C17118.2 (3)C12—N6—Cu1131.4 (3)
C21—C16—C15120.7 (4)C11—N6—Cu1125.6 (3)
C17—C16—C15120.8 (4)C14—N7—C13102.9 (3)
C18—C17—C16120.4 (3)C14—N7—Cu1127.8 (3)
C18—C17—H17119.8C13—N7—Cu1129.2 (3)
C16—C17—H17119.8C13—N8—N9101.8 (3)
C17—C18—C19121.0 (3)C14—N9—N8110.9 (3)
C17—C18—H18119.5C14—N9—C15128.0 (4)
C19—C18—H18119.5N8—N9—C15120.9 (3)
C20—C19—C18118.5 (3)C24iv—N10—N11110.1 (3)
C20—C19—C22122.4 (3)C24iv—N10—C22129.4 (3)
C18—C19—C22119.1 (3)N11—N10—C22120.5 (3)
C19—C20—C21120.1 (3)C23iv—N11—N10103.2 (3)
C19—C20—H20120.0C24—N12—C23103.1 (3)
C21—C20—H20120.0C24—N12—Cu1131.2 (2)
C16—C21—C20121.7 (3)C23—N12—Cu1125.6 (3)
C16—C21—H21119.2C26—N13—H13A119.9
C20—C21—H21119.2C26—N13—H13B120.1
N10—C22—C19112.1 (3)H13A—N13—H13B120.0
N10—C22—H22A109.2C33—N14—H14A120.0
C19—C22—H22A109.2C33—N14—H14B120.0
N10—C22—H22B109.2H14A—N14—H14B120.0
C19—C22—H22B109.2S1—O1—Cu1155.67 (19)
H22A—C22—H22B107.9C31—O5—H5A109.4
N11ii—C23—N12114.1 (4)C38—O9—H9A109.4
N11ii—C23—H23122.9Cu1—O1W—H1WA81.9
N12—C23—H23122.9Cu1—O1W—H1WB164.6
N10ii—C24—N12109.5 (3)H1WA—O1W—H1WB109.3
N10ii—C24—H24125.3H2WB—O2W—H2WA110.4
N12—C24—H24125.3H3WB—O3W—H3WA108.8
C30—C25—C26119.2 (4)H4WA—O4W—H4WB108.5
C30—C25—C31119.2 (4)H5WA—O5W—H5WB106.7
C26—C25—C31121.6 (4)O1—S1—O3112.2 (2)
N13—C26—C25122.6 (4)O1—S1—O2112.3 (2)
N13—C26—C27118.7 (4)O3—S1—O2113.4 (2)
C25—C26—C27118.7 (4)O1—S1—C28106.10 (17)
C28—C27—C26121.0 (4)O3—S1—C28105.27 (18)
C28—C27—H27119.5O2—S1—C28106.86 (18)
C26—C27—H27119.5O8—S2—O6114.9 (2)
C27—C28—C29120.3 (4)O8—S2—O7112.0 (3)
C27—C28—S1119.6 (3)O6—S2—O7110.8 (3)
C29—C28—S1120.1 (3)O8—S2—C35106.0 (2)
C30—C29—C28119.0 (4)O6—S2—C35106.1 (2)
C30—C29—H29120.5O7—S2—C35106.4 (2)
C28—C29—H29120.5
N3—C3—C4—C996.1 (4)N1—C1—N3—C3177.3 (3)
N3—C3—C4—C585.6 (5)C2—N2—N3—C10.3 (4)
C9—C4—C5—C61.2 (6)C2—N2—N3—C3176.8 (3)
C3—C4—C5—C6177.1 (4)C4—C3—N3—C1122.5 (4)
C4—C5—C6—C70.8 (6)C4—C3—N3—N261.1 (5)
C5—C6—C7—C80.3 (6)C7—C10—N4—C12iii113.0 (4)
C5—C6—C7—C10178.2 (4)C7—C10—N4—N563.2 (5)
C6—C7—C8—C90.3 (6)C12iii—N4—N5—C11iii0.1 (4)
C10—C7—C8—C9178.3 (4)C10—N4—N5—C11iii176.7 (3)
C7—C8—C9—C40.7 (6)N4i—C12—N6—C110.7 (4)
C5—C4—C9—C81.1 (6)N4i—C12—N6—Cu1179.0 (2)
C3—C4—C9—C8177.2 (3)N5i—C11—N6—C120.7 (4)
C6—C7—C10—N4135.1 (4)N5i—C11—N6—Cu1179.0 (3)
C8—C7—C10—N446.4 (5)N7—Cu1—N6—C12122.5 (3)
N9—C15—C16—C2196.5 (5)N1—Cu1—N6—C1262.9 (3)
N9—C15—C16—C1789.1 (5)O1W—Cu1—N6—C1220.2 (3)
C21—C16—C17—C182.8 (5)O1—Cu1—N6—C12147.9 (3)
C15—C16—C17—C18171.8 (3)N7—Cu1—N6—C1157.9 (3)
C16—C17—C18—C190.7 (6)N1—Cu1—N6—C11116.8 (3)
C17—C18—C19—C202.3 (5)O1W—Cu1—N6—C11160.1 (3)
C17—C18—C19—C22175.6 (3)O1—Cu1—N6—C1131.8 (3)
C18—C19—C20—C213.1 (5)N9—C14—N7—C130.5 (4)
C22—C19—C20—C21174.7 (3)N9—C14—N7—Cu1176.7 (2)
C17—C16—C21—C202.0 (5)N8—C13—N7—C140.2 (5)
C15—C16—C21—C20172.6 (3)N8—C13—N7—Cu1176.3 (3)
C19—C20—C21—C161.0 (5)N12—Cu1—N7—C14130.9 (3)
C20—C19—C22—N1033.1 (5)N6—Cu1—N7—C1448.5 (3)
C18—C19—C22—N10144.7 (3)O1W—Cu1—N7—C1440.3 (3)
C30—C25—C26—N13174.9 (5)O1—Cu1—N7—C14141.3 (3)
C31—C25—C26—N135.2 (7)N12—Cu1—N7—C1353.9 (4)
C30—C25—C26—C272.4 (7)N6—Cu1—N7—C13126.7 (4)
C31—C25—C26—C27177.6 (4)O1W—Cu1—N7—C13144.4 (4)
N13—C26—C27—C28177.2 (5)O1—Cu1—N7—C1333.9 (4)
C25—C26—C27—C280.2 (7)N7—C13—N8—N90.2 (5)
C26—C27—C28—C292.1 (7)N7—C14—N9—N80.7 (4)
C26—C27—C28—S1177.7 (4)N7—C14—N9—C15174.7 (3)
C27—C28—C29—C302.1 (6)C13—N8—N9—C140.5 (5)
S1—C28—C29—C30177.7 (3)C13—N8—N9—C15175.0 (4)
C28—C29—C30—C250.2 (6)C16—C15—N9—C14118.3 (4)
C26—C25—C30—C292.4 (6)C16—C15—N9—N868.2 (5)
C31—C25—C30—C29177.5 (4)C19—C22—N10—C24iv119.7 (4)
C30—C25—C31—O4179.0 (4)C19—C22—N10—N1159.2 (4)
C26—C25—C31—O41.0 (7)C24iv—N10—N11—C23iv1.0 (4)
C30—C25—C31—O50.3 (6)C22—N10—N11—C23iv178.2 (3)
C26—C25—C31—O5179.7 (4)N10ii—C24—N12—C230.4 (4)
C37—C32—C33—N14179.0 (4)N10ii—C24—N12—Cu1175.3 (2)
C38—C32—C33—N140.6 (6)N11ii—C23—N12—C240.2 (4)
C37—C32—C33—C341.7 (6)N11ii—C23—N12—Cu1176.2 (3)
C38—C32—C33—C34179.9 (4)N7—Cu1—N12—C2473.8 (3)
N14—C33—C34—C35179.9 (4)N1—Cu1—N12—C24100.9 (3)
C32—C33—C34—C350.5 (6)O1W—Cu1—N12—C24176.0 (3)
C33—C34—C35—C361.3 (6)O1—Cu1—N12—C2415.9 (3)
C33—C34—C35—S2178.0 (3)N7—Cu1—N12—C23101.1 (3)
C34—C35—C36—C371.8 (6)N1—Cu1—N12—C2384.3 (3)
S2—C35—C36—C37177.4 (3)O1W—Cu1—N12—C231.2 (3)
C35—C36—C37—C320.6 (6)O1—Cu1—N12—C23169.2 (3)
C33—C32—C37—C361.2 (6)N7—Cu1—O1—S185.2 (4)
C38—C32—C37—C36179.5 (4)N1—Cu1—O1—S195.4 (4)
C37—C32—C38—O10179.1 (5)N12—Cu1—O1—S1174.9 (4)
C33—C32—C38—O102.6 (7)N6—Cu1—O1—S12.2 (4)
C37—C32—C38—O92.2 (6)O1W—Cu1—O1—S1102.6 (6)
C33—C32—C38—O9176.1 (4)Cu1—O1—S1—O3177.4 (4)
N3—C1—N1—C21.0 (4)Cu1—O1—S1—O248.3 (5)
N3—C1—N1—Cu1178.8 (2)Cu1—O1—S1—C2868.1 (4)
N2—C2—N1—C11.2 (5)C27—C28—S1—O1143.4 (3)
N2—C2—N1—Cu1178.8 (3)C29—C28—S1—O136.9 (4)
N12—Cu1—N1—C148.4 (3)C27—C28—S1—O324.3 (4)
N6—Cu1—N1—C1131.9 (3)C29—C28—S1—O3156.0 (3)
O1W—Cu1—N1—C1139.1 (3)C27—C28—S1—O296.6 (4)
O1—Cu1—N1—C139.4 (3)C29—C28—S1—O283.1 (4)
N12—Cu1—N1—C2128.7 (3)C34—C35—S2—O8126.5 (4)
N6—Cu1—N1—C251.0 (4)C36—C35—S2—O854.2 (4)
O1W—Cu1—N1—C238.0 (3)C34—C35—S2—O6111.0 (4)
O1—Cu1—N1—C2143.5 (3)C36—C35—S2—O668.3 (4)
N1—C2—N2—N31.0 (5)C34—C35—S2—O77.1 (4)
N1—C1—N3—N20.5 (4)C36—C35—S2—O7173.6 (4)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y1/2, z+1/2; (iii) x+1, y1/2, z+1/2; (iv) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WB···O2v0.852.582.931 (5)106
O1W—H1WB···O4Wvi0.852.462.897 (5)113
O2W—H2WA···O30.852.102.900 (5)156
O3W—H3WA···O60.851.912.743 (6)165
O4W—H4WA···O70.861.842.678 (6)163
O3W—H3WB···O30.861.922.746 (5)163
O4W—H4WB···O3Wvii0.861.862.712 (5)174
O5W—H5WB···O3Wvii0.862.132.697 (10)123
O5—H5A···O2Wi0.821.822.620 (4)166
O9—H9A···O4Wiv0.821.822.631 (6)172
Symmetry codes: (i) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x, y+3/2, z+1/2; (vi) x, y+1, z; (vii) x, y+1/2, z+1/2.
Poly[[bis(µ2-2-amino-4-sulfonatobenzoato-κ3O4:N,O4')tetraaqua[µ2-1,4-bis(triazol-1-ylmethyl)benzene-κ2N1:N1']dicopper(II)] tetrahydrate] (2) top
Crystal data top
[Cu2(C7H5NO5S)2(C14H14N4)(H2O)4]·4H2OF(000) = 968
Mr = 939.90Dx = 1.679 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 6621 reflections
a = 13.4947 (16) Åθ = 2.5–27.2°
b = 10.1948 (11) ŵ = 1.34 mm1
c = 18.8909 (16) ÅT = 293 K
β = 134.327 (5)°Massive, blue
V = 1859.2 (3) Å30.25 × 0.2 × 0.15 mm
Z = 2
Data collection top
CCD area detector
diffractometer
4280 independent reflections
Radiation source: fine-focus sealed tube3100 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
phi and ω scansθmax = 27.6°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements)
(SADABS; Bruker, 2002)
h = 1716
Tmin = 0.732, Tmax = 0.818k = 1310
18121 measured reflectionsl = 2324
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0391P)2 + 1.7411P]
where P = (Fo2 + 2Fc2)/3
4280 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.49 e Å3
65 restraintsΔρmin = 0.52 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/UeqOcc. (<1)
C10.1985 (3)0.5704 (2)0.42966 (19)0.0196 (6)
C20.1768 (3)0.4342 (2)0.41821 (19)0.0186 (6)
C30.2835 (3)0.3511 (3)0.4905 (2)0.0231 (6)
H30.27010.26090.48250.028*
C40.4106 (3)0.4013 (3)0.5751 (2)0.0272 (7)
C50.4283 (3)0.5346 (3)0.5898 (2)0.0353 (8)
H50.51130.56850.64830.042*
C60.3228 (3)0.6176 (3)0.5178 (2)0.0305 (7)
H60.33530.70770.52860.037*
C70.0970 (3)0.6657 (2)0.3481 (2)0.0197 (6)
C80.0010 (3)0.6057 (3)0.0859 (2)0.0273 (7)
H80.09030.62700.14220.033*
C90.1982 (3)0.5938 (3)0.0677 (2)0.0363 (8)
H90.26790.60430.13600.044*
C100.2064 (3)0.5263 (3)0.0104 (2)0.0307 (7)
H100.28430.48180.03310.037*
C110.0069 (4)0.7210 (3)0.0331 (3)0.0414 (9)
H11A0.06050.70650.10250.050*
H11B0.08680.69080.00490.050*
C120.0035 (3)0.8664 (3)0.0155 (2)0.0303 (7)
C130.1150 (4)0.9446 (3)0.0888 (2)0.0386 (8)
H130.19270.90780.14880.046*
C140.1114 (4)0.9226 (3)0.0730 (2)0.0379 (8)
H140.18710.87040.12250.046*
Cu10.02625 (4)0.44961 (3)0.20296 (2)0.02237 (12)
N10.0468 (3)0.3814 (2)0.33106 (17)0.0206 (5)
H1A0.045 (3)0.2981 (11)0.326 (2)0.040 (10)*
H1B0.020 (2)0.399 (3)0.325 (2)0.037 (10)*
N20.0830 (3)0.5336 (2)0.08566 (16)0.0236 (5)
N30.0672 (3)0.6433 (2)0.00532 (18)0.0294 (6)
O10.0110 (2)0.62843 (17)0.25905 (14)0.0273 (5)
O20.1070 (2)0.78215 (17)0.37282 (13)0.0261 (5)
O30.5439 (4)0.1980 (4)0.6018 (2)0.0878 (14)0.883 (3)
O3'0.6475 (19)0.313 (2)0.6538 (16)0.0878 (14)0.117 (3)
O40.5192 (3)0.2285 (4)0.7126 (2)0.0778 (12)0.883 (3)
O4'0.506 (2)0.1579 (12)0.6447 (15)0.0778 (12)0.117 (3)
O50.6716 (3)0.3674 (3)0.7240 (2)0.0785 (13)0.883 (3)
O5'0.611 (2)0.3358 (19)0.7596 (9)0.0785 (13)0.117 (3)
O1W0.2376 (3)0.4630 (2)0.1641 (2)0.0653 (9)
H1WA0.30120.40900.14240.078*
H1WB0.25890.53910.16670.078*
O2W0.2022 (2)0.4086 (2)0.26747 (16)0.0427 (6)
H2WA0.25140.47650.28830.051*
H2WB0.22150.33770.25560.051*
O3W0.3816 (3)0.2988 (2)0.89294 (19)0.0548 (7)
H3WA0.44230.29290.95560.066*
H3WB0.41840.32940.87390.066*
O4W0.4732 (3)0.4025 (3)0.8134 (2)0.0777 (9)
H4WA0.48570.35110.78480.093*
H4WB0.49100.48050.81020.093*
S10.54915 (8)0.29130 (8)0.66184 (6)0.0379 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0221 (14)0.0144 (13)0.0211 (14)0.0016 (11)0.0146 (12)0.0011 (10)
C20.0211 (14)0.0153 (13)0.0181 (13)0.0014 (11)0.0132 (12)0.0007 (10)
C30.0280 (16)0.0129 (13)0.0263 (15)0.0012 (12)0.0182 (13)0.0031 (11)
C40.0226 (15)0.0239 (15)0.0239 (15)0.0038 (13)0.0121 (13)0.0057 (12)
C50.0227 (16)0.0270 (17)0.0279 (16)0.0014 (14)0.0073 (14)0.0019 (13)
C60.0290 (17)0.0142 (14)0.0315 (16)0.0036 (13)0.0149 (14)0.0037 (12)
C70.0243 (15)0.0132 (12)0.0247 (15)0.0007 (12)0.0183 (13)0.0015 (11)
C80.0316 (17)0.0176 (14)0.0255 (16)0.0003 (13)0.0173 (14)0.0000 (12)
C90.041 (2)0.0290 (16)0.0247 (16)0.0023 (15)0.0176 (15)0.0030 (13)
C100.0278 (17)0.0260 (16)0.0276 (16)0.0029 (13)0.0155 (14)0.0017 (13)
C110.073 (3)0.0239 (16)0.060 (2)0.0012 (17)0.059 (2)0.0009 (15)
C120.046 (2)0.0230 (15)0.0409 (18)0.0006 (15)0.0375 (17)0.0046 (14)
C130.0383 (19)0.0333 (18)0.0333 (17)0.0029 (16)0.0211 (16)0.0003 (15)
C140.0390 (19)0.0302 (17)0.0386 (19)0.0090 (15)0.0249 (17)0.0111 (14)
Cu10.0317 (2)0.01008 (16)0.01832 (18)0.00197 (15)0.01493 (16)0.00001 (13)
N10.0217 (13)0.0127 (12)0.0219 (12)0.0020 (10)0.0133 (11)0.0002 (10)
N20.0331 (14)0.0118 (11)0.0212 (12)0.0010 (10)0.0173 (11)0.0009 (9)
N30.0458 (17)0.0176 (12)0.0337 (14)0.0010 (12)0.0311 (14)0.0019 (11)
O10.0347 (12)0.0122 (9)0.0186 (10)0.0002 (9)0.0126 (9)0.0008 (8)
O20.0368 (12)0.0110 (9)0.0231 (10)0.0043 (9)0.0182 (10)0.0003 (8)
O30.068 (2)0.084 (3)0.056 (2)0.053 (2)0.0232 (17)0.0026 (18)
O3'0.068 (2)0.084 (3)0.056 (2)0.053 (2)0.0232 (17)0.0026 (18)
O40.059 (2)0.085 (3)0.077 (2)0.0279 (19)0.0430 (19)0.056 (2)
O4'0.059 (2)0.085 (3)0.077 (2)0.0279 (19)0.0430 (19)0.056 (2)
O50.0245 (15)0.0466 (18)0.075 (2)0.0029 (14)0.0020 (14)0.0232 (17)
O5'0.0245 (15)0.0466 (18)0.075 (2)0.0029 (14)0.0020 (14)0.0232 (17)
O1W0.0418 (16)0.0402 (15)0.110 (2)0.0015 (13)0.0518 (17)0.0052 (15)
O2W0.0397 (14)0.0419 (13)0.0473 (14)0.0006 (12)0.0306 (12)0.0008 (11)
O3W0.0521 (16)0.0493 (16)0.0603 (17)0.0007 (13)0.0383 (15)0.0008 (13)
O4W0.072 (2)0.086 (2)0.079 (2)0.0112 (19)0.0541 (19)0.0051 (19)
S10.0252 (4)0.0271 (4)0.0350 (4)0.0069 (3)0.0114 (4)0.0092 (3)
Geometric parameters (Å, º) top
C1—C61.384 (4)C13—C14i1.380 (4)
C1—C21.404 (3)C13—H130.9300
C1—C71.498 (4)C14—C13i1.380 (4)
C2—C31.381 (4)C14—H140.9300
C2—N11.429 (3)Cu1—N11.994 (2)
C3—C41.388 (4)Cu1—N21.964 (2)
C3—H30.9300Cu1—O11.9885 (18)
C4—C51.374 (4)Cu1—O2ii1.9929 (18)
C4—S11.776 (3)Cu1—O1W2.402 (3)
C5—C61.374 (4)Cu1—O2W2.431 (2)
C5—H50.9300Cu1—H1B2.32 (3)
C6—H60.9300N1—H1A0.854 (10)
C7—O21.248 (3)N1—H1B0.857 (10)
C7—O11.262 (3)O2—Cu1iii1.9929 (18)
C8—N21.326 (4)O3—S11.444 (3)
C8—N31.328 (4)O3'—S11.455 (9)
C8—H80.9300O4—S11.427 (3)
C9—C101.351 (4)O4'—S11.427 (9)
C9—N31.363 (4)O5—S11.414 (3)
C9—H90.9300O5'—S11.472 (9)
C10—N21.360 (4)O1W—H1WA0.8457
C10—H100.9300O1W—H1WB0.8401
C11—N31.469 (4)O2W—H2WA0.8423
C11—C121.512 (4)O2W—H2WB0.8500
C11—H11A0.9700O3W—H3WA0.8483
C11—H11B0.9700O3W—H3WB0.8500
C12—C141.380 (4)O4W—H4WA0.8501
C12—C131.381 (4)O4W—H4WB0.8454
C6—C1—C2118.4 (2)O1—Cu1—O1W85.11 (9)
C6—C1—C7118.7 (2)O2ii—Cu1—O1W83.85 (9)
C2—C1—C7122.7 (2)N1—Cu1—O1W82.27 (10)
C3—C2—C1119.5 (2)N2—Cu1—O2W89.93 (9)
C3—C2—N1120.0 (2)O1—Cu1—O2W97.50 (8)
C1—C2—N1120.4 (2)O2ii—Cu1—O2W94.47 (8)
C2—C3—C4120.6 (3)N1—Cu1—O2W87.31 (9)
C2—C3—H3119.7O1W—Cu1—O2W169.12 (9)
C4—C3—H3119.7C2—N1—Cu1115.74 (17)
C5—C4—C3119.8 (3)C2—N1—H1A115 (2)
C5—C4—S1121.1 (2)Cu1—N1—H1A105 (2)
C3—C4—S1119.1 (2)C2—N1—H1B114 (2)
C6—C5—C4119.7 (3)Cu1—N1—H1B101 (2)
C6—C5—H5120.1H1A—N1—H1B105 (3)
C4—C5—H5120.1C8—N2—C10106.0 (2)
C5—C6—C1121.6 (3)C8—N2—Cu1124.82 (19)
C5—C6—H6119.2C10—N2—Cu1129.1 (2)
C1—C6—H6119.2C8—N3—C9107.7 (3)
O2—C7—O1122.9 (2)C8—N3—C11125.5 (3)
O2—C7—C1116.7 (2)C9—N3—C11126.7 (3)
O1—C7—C1120.3 (2)C7—O1—Cu1129.86 (17)
N2—C8—N3110.7 (3)C7—O2—Cu1iii133.14 (18)
N2—C8—H8124.7Cu1—O1W—H1WA134.1
N3—C8—H8124.7Cu1—O1W—H1WB114.6
C10—C9—N3106.2 (3)H1WA—O1W—H1WB110.9
C10—C9—H9126.9Cu1—O2W—H2WA113.8
N3—C9—H9126.9Cu1—O2W—H2WB121.9
C9—C10—N2109.4 (3)H2WA—O2W—H2WB122.3
C9—C10—H10125.3H3WA—O3W—H3WB109.7
N2—C10—H10125.3H4WA—O4W—H4WB109.9
N3—C11—C12112.9 (3)O5—S1—O4113.8 (2)
N3—C11—H11A109.0O5—S1—O4'140.3 (9)
C12—C11—H11A109.0O4—S1—O4'57.3 (9)
N3—C11—H11B109.0O5—S1—O3113.6 (2)
C12—C11—H11B109.0O4—S1—O3110.6 (2)
H11A—C11—H11B107.8O4'—S1—O353.7 (9)
C14—C12—C13119.3 (3)O5—S1—O3'51.7 (8)
C14—C12—C11120.6 (3)O4—S1—O3'147.9 (9)
C13—C12—C11120.1 (3)O4'—S1—O3'112.6 (8)
C14i—C13—C12120.1 (3)O3—S1—O3'64.3 (8)
C14i—C13—H13119.9O5—S1—O5'58.8 (8)
C12—C13—H13119.9O4—S1—O5'58.0 (8)
C13i—C14—C12120.6 (3)O4'—S1—O5'111.1 (8)
C13i—C14—H14119.7O3—S1—O5'149.9 (8)
C12—C14—H14119.7O3'—S1—O5'109.2 (8)
N2—Cu1—O187.45 (8)O5—S1—C4106.57 (16)
N2—Cu1—O2ii88.65 (8)O4—S1—C4107.04 (17)
O1—Cu1—O2ii167.40 (8)O4'—S1—C4113.0 (9)
N2—Cu1—N1173.38 (10)O3—S1—C4104.42 (16)
O1—Cu1—N186.94 (9)O3'—S1—C4104.9 (9)
O2ii—Cu1—N197.56 (8)O5'—S1—C4105.6 (8)
N2—Cu1—O1W100.76 (10)
C6—C1—C2—C35.9 (4)O2ii—Cu1—N2—C8129.9 (2)
C7—C1—C2—C3169.7 (2)O1W—Cu1—N2—C8146.6 (2)
C6—C1—C2—N1176.0 (3)O2W—Cu1—N2—C835.5 (2)
C7—C1—C2—N18.4 (4)O1—Cu1—N2—C10121.7 (3)
C1—C2—C3—C41.4 (4)O2ii—Cu1—N2—C1046.3 (2)
N1—C2—C3—C4179.5 (3)O1W—Cu1—N2—C1037.1 (3)
C2—C3—C4—C53.7 (5)O2W—Cu1—N2—C10140.8 (2)
C2—C3—C4—S1175.2 (2)N2—C8—N3—C90.1 (3)
C3—C4—C5—C64.1 (5)N2—C8—N3—C11178.1 (2)
S1—C4—C5—C6174.8 (3)C10—C9—N3—C80.0 (4)
C4—C5—C6—C10.6 (5)C10—C9—N3—C11178.2 (3)
C2—C1—C6—C55.5 (5)C12—C11—N3—C881.0 (4)
C7—C1—C6—C5170.2 (3)C12—C11—N3—C9101.1 (4)
C6—C1—C7—O223.2 (4)O2—C7—O1—Cu1178.2 (2)
C2—C1—C7—O2161.2 (3)C1—C7—O1—Cu15.0 (4)
C6—C1—C7—O1153.8 (3)N2—Cu1—O1—C7151.0 (3)
C2—C1—C7—O121.8 (4)O2ii—Cu1—O1—C7136.8 (3)
N3—C9—C10—N20.1 (4)N1—Cu1—O1—C725.4 (3)
N3—C11—C12—C1491.9 (4)O1W—Cu1—O1—C7107.9 (3)
N3—C11—C12—C1389.0 (4)O2W—Cu1—O1—C761.4 (3)
C14—C12—C13—C14i0.4 (5)O1—C7—O2—Cu1iii9.9 (4)
C11—C12—C13—C14i179.5 (3)C1—C7—O2—Cu1iii166.97 (19)
C13—C12—C14—C13i0.4 (5)C5—C4—S1—O514.5 (4)
C11—C12—C14—C13i179.5 (3)C3—C4—S1—O5164.3 (3)
C3—C2—N1—Cu1128.6 (2)C5—C4—S1—O4107.6 (3)
C1—C2—N1—Cu149.5 (3)C3—C4—S1—O473.6 (3)
O1—Cu1—N1—C249.3 (2)C5—C4—S1—O4'168.6 (10)
O2ii—Cu1—N1—C2142.48 (19)C3—C4—S1—O4'12.5 (10)
O1W—Cu1—N1—C2134.8 (2)C5—C4—S1—O3135.1 (3)
O2W—Cu1—N1—C248.33 (19)C3—C4—S1—O343.7 (3)
N3—C8—N2—C100.2 (3)C5—C4—S1—O3'68.4 (9)
N3—C8—N2—Cu1176.82 (18)C3—C4—S1—O3'110.5 (9)
C9—C10—N2—C80.1 (3)C5—C4—S1—O5'46.9 (9)
C9—C10—N2—Cu1176.7 (2)C3—C4—S1—O5'134.2 (9)
O1—Cu1—N2—C862.1 (2)
Symmetry codes: (i) x, y+2, z; (ii) x, y1/2, z+1/2; (iii) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O3iv0.851.982.814 (4)171
O1W—H1WB···O3Wv0.842.032.812 (4)154
O2W—H2WA···O5vi0.842.002.785 (4)155
O2W—H2WB···O3Wvii0.852.352.817 (3)115
O3W—H3WA···O3viii0.852.062.879 (4)163
O3W—H3WB···O4W0.851.892.737 (4)172
O4W—H4WA···O40.852.122.968 (5)178
N1—H1A···O1ii0.85 (1)2.11 (2)2.881 (3)151 (3)
Symmetry codes: (ii) x, y1/2, z+1/2; (iv) x1, y+1/2, z1/2; (v) x, y+1, z+1; (vi) x+1, y+1, z+1; (vii) x, y+1/2, z1/2; (viii) x, y+1/2, z+1/2.
 

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