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By employing the conjugated bi­thio­phene ligand 5,5′-bis­(1H-imidazol-1-yl)-2,2′-bi­thio­phene (bibp), which can exhibit trans and cis conformations, two different CuII coordination polymers, namely, poly[[μ-5,5′-bis­(1H-imidazol-1-yl)-2,2′-bi­thio­phene-κ2N:N′](μ2-4,4′-oxydibenzoato-κ2O:O′)copper(II)], [Cu(C14H8O5)(C14H10N4S2)]n or [Cu(bibp)(oba)]n, (I), and catena-poly[μ-aqua-bis­[μ-5,5′-bis­(1H-imidazol-1-yl)-2,2′-bi­thio­phene-κ2N:N′]bis­(μ3-4,4′-oxydibenzoato)-κ3O:O′:O′′;κ4O:O′,O′′:O′-dicopper(II)], [Cu2(C14H8O5)2(C14H10N4S2)(H2O)]n or [Cu2(bibp)(oba)2(H2O)]n, (II), have been prepared through one-pot concomitant crystallization and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis, powder X-ray diffraction (PXRD) and thermogravimetric (TG) analysis. Single-crystal X-ray diffraction indicates that the most inter­esting aspect of the structure is the existence of sole trans and cis conformations of the bibp ligand in a single net of (I) and (II), respectively. Compound (I) displays a threefold inter­penetrating three-dimensional framework with a 4-connected {65.8} cds topology, whereas (II) features a one-dimensional chain structure. In the crystal of (II), the polymeric chains are further extended through C—H...O hydrogen bonds and C—H...π inter­actions into a three-dimensional supra­molecular architecture. In addition, strong intra­molecular O—H...O hydrogen bonds formed between the bridging water mol­ecules and the carboxyl­ate O atoms improve the stability of the framework of (II). Furthermore, solid-state UV–Vis spectroscopy experiments show that com­pounds (I) and (II) exhibit optical band gaps which are characteristic for optical semiconductors, with values of 2.70 and 2.26 eV, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619016024/lf3106sup1.cif
Contains datablocks 1, 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619016024/lf31061sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619016024/lf31062sup3.hkl
Contains datablock 2

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619016024/lf3106sup4.pdf
HOMO-LUMO energy values, PXRD patterns and TG curves

CCDC references: 1968717; 1968716

Computing details top

For both structures, data collection: SMART (Bruker, 2008); cell refinement: SMART (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Bruker, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: SHELXTL (Bruker, 2008); software used to prepare material for publication: SHELXTL (Bruker, 2008).

Poly[[µ-5,5'-bis(1H-imidazol-1-yl)-2,2'-bithiophene-κ2N:N'](µ2-4,4'-oxydibenzoato-κ2O:O')copper(II)] (1) top
Crystal data top
[Cu(C14H8O5)(C14H10N4S2)]F(000) = 1260
Mr = 618.12Dx = 1.556 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 21.086 (2) ÅCell parameters from 3106 reflections
b = 8.0671 (9) Åθ = 2.6–27.8°
c = 15.9578 (18) ŵ = 1.03 mm1
β = 103.623 (2)°T = 296 K
V = 2638.1 (5) Å3Block, purple
Z = 40.22 × 0.18 × 0.15 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
2065 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1824
Tmin = 0.804, Tmax = 0.860k = 99
7319 measured reflectionsl = 1818
2327 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.070P)2 + 0.050P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2327 reflectionsΔρmax = 0.41 e Å3
183 parametersΔρmin = 0.33 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.20466 (11)1.1425 (3)0.63356 (14)0.0343 (5)
C20.15081 (10)1.0717 (3)0.66902 (12)0.0309 (5)
C30.08837 (11)1.1373 (3)0.64663 (15)0.0429 (6)
H30.0802891.2309810.6117550.051*
C40.03778 (11)1.0652 (3)0.67556 (15)0.0452 (6)
H40.0038181.1111610.6610880.054*
C50.04960 (10)0.9252 (3)0.72574 (13)0.0328 (5)
C60.11160 (10)0.8584 (3)0.74991 (13)0.0347 (5)
H60.1193290.7648780.7848900.042*
C70.16194 (10)0.9318 (3)0.72167 (13)0.0338 (5)
H70.2037390.8872980.7379450.041*
C80.16325 (10)0.9592 (3)0.45973 (13)0.0332 (5)
H80.1328691.0074010.4860650.040*
C90.24706 (10)0.9208 (3)0.40701 (13)0.0341 (5)
H90.2858630.9395230.3903970.041*
C100.21172 (11)0.7793 (3)0.39262 (15)0.0346 (5)
H100.2215460.6840390.3653770.042*
C110.10942 (10)0.6883 (3)0.43175 (14)0.0330 (5)
C120.08717 (14)0.5635 (3)0.37742 (18)0.0593 (8)
H120.1019440.5403440.3281750.071*
C130.03836 (15)0.4711 (3)0.40424 (19)0.0655 (9)
H130.0180700.3790590.3743910.079*
C140.02381 (10)0.5290 (3)0.47769 (14)0.0368 (5)
Cu10.2500001.2500000.5000000.03018 (16)
N10.21706 (8)1.0322 (2)0.44976 (10)0.0324 (4)
N20.15858 (8)0.8049 (2)0.42631 (11)0.0314 (4)
O10.18625 (9)1.24528 (17)0.57038 (11)0.0391 (4)
O20.26154 (7)1.0953 (2)0.66033 (11)0.0464 (4)
O30.0000000.8380 (3)0.7500000.0424 (5)
S10.07192 (3)0.69825 (8)0.51615 (4)0.03957 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0359 (13)0.0293 (11)0.0433 (12)0.0087 (9)0.0204 (10)0.0119 (9)
C20.0315 (11)0.0313 (11)0.0341 (10)0.0042 (8)0.0161 (9)0.0014 (8)
C30.0421 (13)0.0392 (13)0.0541 (13)0.0082 (10)0.0247 (11)0.0180 (11)
C40.0311 (12)0.0506 (14)0.0606 (14)0.0125 (10)0.0244 (11)0.0166 (12)
C50.0331 (12)0.0360 (11)0.0367 (11)0.0011 (9)0.0231 (9)0.0006 (9)
C60.0388 (12)0.0333 (12)0.0368 (11)0.0034 (9)0.0186 (9)0.0073 (9)
C70.0265 (11)0.0396 (12)0.0368 (11)0.0044 (9)0.0103 (9)0.0031 (9)
C80.0311 (11)0.0304 (11)0.0411 (11)0.0072 (9)0.0143 (9)0.0046 (9)
C90.0298 (11)0.0360 (12)0.0403 (11)0.0043 (9)0.0161 (9)0.0027 (9)
C100.0325 (12)0.0338 (11)0.0410 (12)0.0013 (9)0.0156 (10)0.0002 (9)
C110.0279 (11)0.0277 (11)0.0458 (12)0.0057 (9)0.0135 (9)0.0011 (9)
C120.0713 (19)0.0476 (15)0.0748 (17)0.0302 (14)0.0487 (15)0.0303 (13)
C130.072 (2)0.0460 (16)0.093 (2)0.0370 (14)0.0499 (17)0.0378 (15)
C140.0319 (12)0.0259 (11)0.0545 (13)0.0089 (8)0.0144 (10)0.0047 (9)
Cu10.0312 (2)0.0261 (2)0.0378 (2)0.01012 (13)0.01726 (17)0.00040 (13)
N10.0323 (10)0.0312 (10)0.0366 (9)0.0094 (7)0.0137 (8)0.0003 (7)
N20.0307 (10)0.0260 (9)0.0403 (10)0.0087 (7)0.0140 (8)0.0018 (7)
O10.0425 (10)0.0305 (9)0.0524 (10)0.0074 (6)0.0273 (8)0.0030 (6)
O20.0306 (9)0.0473 (10)0.0651 (10)0.0087 (7)0.0189 (8)0.0076 (8)
O30.0399 (13)0.0329 (12)0.0673 (14)0.0000.0384 (11)0.000
S10.0392 (4)0.0401 (4)0.0425 (3)0.0197 (3)0.0158 (3)0.0086 (2)
Geometric parameters (Å, º) top
C1—O21.235 (3)C9—N11.370 (3)
C1—O11.292 (3)C9—H90.9300
C1—C21.496 (3)C10—N21.368 (3)
C2—C31.386 (3)C10—H100.9300
C2—C71.394 (3)C11—C121.340 (3)
C3—C41.386 (3)C11—N21.417 (3)
C3—H30.9300C11—S11.717 (2)
C4—C51.372 (3)C12—C131.416 (3)
C4—H40.9300C12—H120.9300
C5—C61.382 (3)C13—C141.362 (3)
C5—O31.389 (2)C13—H130.9300
C6—C71.380 (3)C14—C14i1.439 (4)
C6—H60.9300C14—S11.725 (2)
C7—H70.9300Cu1—O1ii1.9444 (16)
C8—N11.321 (3)Cu1—O11.9445 (16)
C8—N21.349 (3)Cu1—N1ii1.9873 (17)
C8—H80.9300Cu1—N11.9873 (17)
C9—C101.353 (3)
O2—C1—O1123.8 (2)N2—C10—H10127.0
O2—C1—C2120.9 (2)C12—C11—N2127.5 (2)
O1—C1—C2115.12 (19)C12—C11—S1112.77 (17)
C3—C2—C7118.66 (18)N2—C11—S1119.72 (16)
C3—C2—C1121.10 (19)C11—C12—C13111.6 (2)
C7—C2—C1120.14 (19)C11—C12—H12124.2
C2—C3—C4120.8 (2)C13—C12—H12124.2
C2—C3—H3119.6C14—C13—C12114.0 (2)
C4—C3—H3119.6C14—C13—H13123.0
C5—C4—C3119.4 (2)C12—C13—H13123.0
C5—C4—H4120.3C13—C14—C14i129.7 (3)
C3—C4—H4120.3C13—C14—S1110.17 (16)
C4—C5—C6120.89 (19)C14i—C14—S1120.1 (2)
C4—C5—O3122.27 (19)O1ii—Cu1—O1180.00 (6)
C6—C5—O3116.71 (19)O1ii—Cu1—N1ii89.55 (6)
C7—C6—C5119.43 (19)O1—Cu1—N1ii90.45 (6)
C7—C6—H6120.3O1ii—Cu1—N190.45 (6)
C5—C6—H6120.3O1—Cu1—N189.55 (6)
C6—C7—C2120.71 (19)N1ii—Cu1—N1180.0
C6—C7—H7119.6C8—N1—C9106.12 (17)
C2—C7—H7119.6C8—N1—Cu1125.04 (14)
N1—C8—N2110.42 (18)C9—N1—Cu1128.50 (14)
N1—C8—H8124.8C8—N2—C10107.72 (17)
N2—C8—H8124.8C8—N2—C11125.07 (18)
C10—C9—N1109.74 (18)C10—N2—C11127.05 (19)
C10—C9—H9125.1C1—O1—Cu1109.97 (14)
N1—C9—H9125.1C5—O3—C5iii119.1 (2)
C9—C10—N2105.99 (19)C11—S1—C1491.42 (10)
C9—C10—H10127.0
Symmetry codes: (i) x, y+1, z+1; (ii) x+1/2, y+5/2, z+1; (iii) x, y, z+3/2.
catena-Poly[µ-aqua-bis[µ-5,5'-bis(1H-imidazol-1-yl)-2,2'-bithiophene-κ2N:N']bis(µ3-4,4'-oxydibenzoato)-κ3O:O':O'';κ4O:O',O'':O'-dicopper(II)] (2) top
Crystal data top
[Cu2(C14H8O5)2(C14H10N4S2)(H2O)]Z = 2
Mr = 955.88F(000) = 972
Triclinic, P1Dx = 1.611 Mg m3
a = 11.140 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.522 (4) ÅCell parameters from 4709 reflections
c = 14.911 (5) Åθ = 2.3–28.2°
α = 74.487 (5)°µ = 1.25 mm1
β = 87.709 (5)°T = 296 K
γ = 79.511 (6)°Block, blue
V = 1970.6 (11) Å30.18 × 0.15 × 0.12 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
5741 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
phi and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 913
Tmin = 0.806, Tmax = 0.864k = 1414
10994 measured reflectionsl = 1715
6892 independent reflections
Refinement top
Refinement on F23 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.090P)2 + 0.0526P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6892 reflectionsΔρmax = 0.61 e Å3
558 parametersΔρmin = 0.45 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.0611 (3)0.6810 (3)0.5244 (2)0.0503 (8)
C21.1430 (3)0.6633 (3)0.4441 (2)0.0440 (7)
C31.1709 (3)0.7533 (3)0.3757 (2)0.0534 (8)
H31.1398640.8262860.3789860.064*
C41.2449 (3)0.7360 (3)0.3020 (2)0.0543 (8)
H41.2628920.7971160.2556360.065*
C51.2916 (3)0.6277 (3)0.2981 (2)0.0481 (8)
C61.2632 (3)0.5357 (3)0.3649 (2)0.0526 (8)
H61.2933160.4627770.3610000.063*
C71.1884 (3)0.5546 (3)0.4381 (2)0.0493 (8)
H71.1685760.4936790.4836280.059*
C81.4739 (3)0.5456 (3)0.2309 (2)0.0437 (7)
C91.5234 (3)0.5221 (3)0.1504 (2)0.0462 (7)
H91.4782320.5472750.0953040.055*
C101.6397 (3)0.4613 (3)0.1522 (2)0.0443 (7)
H101.6740580.4486560.0972520.053*
C111.7064 (2)0.4187 (2)0.23445 (19)0.0361 (6)
C121.6537 (3)0.4410 (3)0.3154 (2)0.0483 (8)
H121.6965090.4117690.3714820.058*
C131.5392 (3)0.5058 (3)0.3137 (2)0.0556 (9)
H131.5062410.5225110.3676510.067*
C141.8328 (2)0.3530 (2)0.23782 (19)0.0366 (6)
C150.6626 (3)0.7173 (3)0.8085 (2)0.0404 (7)
C160.5417 (3)0.7619 (2)0.8454 (2)0.0377 (6)
C170.4442 (3)0.8127 (3)0.7845 (2)0.0502 (8)
H170.4549870.8195010.7212160.060*
C180.3320 (3)0.8531 (3)0.8161 (2)0.0498 (8)
H180.2677110.8875070.7743780.060*
C190.3156 (3)0.8424 (3)0.9090 (2)0.0418 (7)
C200.4099 (3)0.7925 (3)0.9716 (2)0.0539 (9)
H200.3981200.7855121.0348120.065*
C210.5229 (3)0.7528 (3)0.9388 (2)0.0483 (8)
H210.5871470.7193450.9806990.058*
C220.1740 (3)0.9165 (3)1.0142 (2)0.0439 (7)
C230.2350 (3)0.9948 (3)1.0337 (2)0.0486 (8)
H230.3027521.0148690.9993670.058*
C240.1927 (3)1.0429 (3)1.1059 (2)0.0434 (7)
H240.2325751.0956271.1198590.052*
C250.0916 (3)1.0126 (2)1.15710 (18)0.0372 (6)
C260.0342 (3)0.9325 (3)1.1369 (2)0.0442 (7)
H260.0320380.9102991.1723300.053*
C270.0738 (3)0.8854 (3)1.0651 (2)0.0442 (7)
H270.0334170.8330271.0509980.053*
C280.0414 (3)1.0651 (2)1.23312 (19)0.0397 (7)
C290.7357 (3)0.9707 (3)0.6132 (2)0.0469 (7)
H290.7146340.9470390.6754570.056*
C300.8312 (3)0.9850 (3)0.4843 (2)0.0627 (10)
H300.8895410.9715160.4403720.075*
C310.7305 (3)1.0631 (3)0.4670 (2)0.0656 (11)
H310.7071721.1145180.4101000.079*
C320.5526 (3)1.1167 (3)0.5622 (2)0.0459 (7)
C330.4722 (5)1.1778 (5)0.4954 (3)0.124 (3)
H330.4853911.1860030.4321280.149*
C340.3648 (5)1.2285 (5)0.5327 (3)0.125 (3)
H340.2985771.2712190.4956940.150*
C350.3657 (3)1.2105 (3)0.6248 (2)0.0503 (8)
C360.2660 (3)1.2515 (3)0.6807 (2)0.0425 (7)
C370.1538 (3)1.2989 (5)0.6495 (3)0.0868 (16)
H370.1286521.3047980.5893210.104*
C380.0753 (3)1.3397 (4)0.7145 (3)0.0834 (15)
H380.0049201.3766910.7017400.100*
C390.1311 (3)1.3183 (2)0.79674 (19)0.0364 (6)
C400.1268 (2)1.3232 (2)0.96229 (19)0.0361 (6)
H400.2088611.2939140.9760930.043*
C410.0631 (3)1.3908 (2)0.9744 (2)0.0407 (7)
H410.1369801.4163470.9996170.049*
C420.0468 (3)1.3880 (2)0.8855 (2)0.0416 (7)
H420.1055991.4113550.8383630.050*
Cu10.97775 (3)0.81790 (3)0.64209 (2)0.04242 (14)
Cu20.92588 (3)0.65891 (3)0.84363 (2)0.03756 (13)
N10.8360 (2)0.9274 (2)0.57667 (17)0.0475 (6)
N20.6673 (2)1.0535 (2)0.54910 (16)0.0465 (6)
N30.0455 (2)1.3505 (2)1.02299 (16)0.0365 (5)
N40.0755 (2)1.34323 (19)0.87786 (15)0.0341 (5)
O11.0284 (2)0.7825 (2)0.52690 (15)0.0649 (7)
O21.0305 (2)0.5983 (2)0.58085 (19)0.0677 (7)
O31.3594 (2)0.6137 (2)0.22003 (15)0.0625 (7)
O41.86325 (18)0.27243 (17)0.30777 (14)0.0422 (5)
O51.89985 (18)0.38544 (18)0.16840 (14)0.0463 (5)
O60.75095 (18)0.68330 (19)0.86798 (14)0.0464 (5)
O70.6704 (2)0.7170 (2)0.72547 (15)0.0627 (7)
O80.19715 (19)0.8754 (2)0.93626 (17)0.0617 (7)
O90.08193 (19)1.15409 (17)1.23885 (13)0.0410 (5)
O100.0319 (2)1.0228 (2)1.28916 (15)0.0573 (6)
O1W0.8969 (2)0.6336 (2)0.72151 (15)0.0515 (6)
S10.49630 (8)1.12098 (10)0.66939 (6)0.0691 (3)
S20.28036 (8)1.25505 (9)0.79443 (6)0.0625 (3)
H1W0.9364 (19)0.621 (3)0.6744 (11)0.066 (11)*
H2W0.8224 (7)0.651 (4)0.7044 (18)0.106 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0317 (16)0.082 (2)0.0431 (18)0.0046 (16)0.0005 (13)0.0370 (18)
C20.0266 (15)0.068 (2)0.0435 (17)0.0038 (14)0.0015 (12)0.0333 (15)
C30.0466 (19)0.057 (2)0.054 (2)0.0134 (15)0.0006 (15)0.0253 (16)
C40.0456 (19)0.064 (2)0.0432 (18)0.0129 (16)0.0047 (14)0.0126 (15)
C50.0296 (15)0.075 (2)0.0361 (16)0.0115 (14)0.0029 (12)0.0227 (15)
C60.0426 (19)0.065 (2)0.054 (2)0.0060 (15)0.0073 (15)0.0327 (17)
C70.0422 (18)0.064 (2)0.0470 (18)0.0052 (15)0.0096 (14)0.0279 (15)
C80.0295 (15)0.0558 (18)0.0393 (16)0.0091 (13)0.0071 (12)0.0136 (13)
C90.0364 (17)0.065 (2)0.0295 (15)0.0102 (14)0.0002 (12)0.0122 (13)
C100.0358 (16)0.0626 (19)0.0311 (15)0.0059 (14)0.0051 (12)0.0169 (13)
C110.0278 (14)0.0440 (16)0.0346 (15)0.0021 (12)0.0063 (11)0.0136 (12)
C120.0342 (17)0.074 (2)0.0307 (15)0.0098 (15)0.0003 (12)0.0159 (14)
C130.0396 (18)0.088 (2)0.0335 (16)0.0146 (16)0.0044 (13)0.0246 (16)
C140.0294 (15)0.0498 (17)0.0322 (15)0.0005 (12)0.0046 (11)0.0184 (13)
C150.0305 (15)0.0573 (18)0.0361 (16)0.0057 (13)0.0053 (12)0.0189 (13)
C160.0297 (15)0.0523 (17)0.0339 (15)0.0055 (12)0.0045 (11)0.0179 (13)
C170.0376 (17)0.082 (2)0.0305 (15)0.0002 (16)0.0011 (12)0.0202 (15)
C180.0355 (17)0.074 (2)0.0393 (17)0.0032 (15)0.0066 (13)0.0214 (15)
C190.0299 (15)0.0535 (18)0.0465 (17)0.0026 (13)0.0030 (12)0.0281 (14)
C200.0389 (18)0.085 (2)0.0345 (16)0.0131 (16)0.0029 (13)0.0274 (16)
C210.0326 (16)0.072 (2)0.0347 (16)0.0079 (14)0.0021 (12)0.0150 (14)
C220.0338 (16)0.0569 (18)0.0410 (16)0.0138 (14)0.0041 (13)0.0271 (14)
C230.0319 (16)0.070 (2)0.0464 (18)0.0005 (15)0.0084 (13)0.0271 (16)
C240.0390 (17)0.0536 (18)0.0413 (17)0.0029 (13)0.0043 (13)0.0229 (14)
C250.0358 (16)0.0410 (15)0.0283 (14)0.0085 (12)0.0006 (11)0.0083 (11)
C260.0448 (18)0.0452 (17)0.0385 (16)0.0003 (13)0.0060 (13)0.0107 (13)
C270.0438 (18)0.0428 (17)0.0461 (18)0.0027 (13)0.0010 (14)0.0186 (14)
C280.0401 (17)0.0435 (17)0.0271 (14)0.0116 (13)0.0019 (12)0.0082 (12)
C290.0440 (18)0.0582 (19)0.0301 (15)0.0133 (14)0.0045 (12)0.0125 (13)
C300.048 (2)0.098 (3)0.0282 (16)0.0179 (19)0.0071 (14)0.0130 (17)
C310.049 (2)0.098 (3)0.0290 (17)0.0177 (19)0.0028 (14)0.0030 (17)
C320.0446 (18)0.0522 (18)0.0312 (15)0.0145 (14)0.0021 (13)0.0102 (13)
C330.116 (4)0.172 (5)0.0272 (19)0.098 (4)0.002 (2)0.010 (2)
C340.104 (4)0.175 (5)0.038 (2)0.099 (4)0.001 (2)0.011 (3)
C350.0458 (19)0.061 (2)0.0352 (17)0.0155 (15)0.0029 (13)0.0135 (14)
C360.0405 (17)0.0526 (18)0.0305 (15)0.0057 (13)0.0014 (12)0.0140 (13)
C370.042 (2)0.168 (5)0.050 (2)0.026 (2)0.0109 (17)0.057 (3)
C380.041 (2)0.157 (4)0.045 (2)0.033 (2)0.0108 (16)0.048 (2)
C390.0333 (15)0.0445 (16)0.0296 (14)0.0005 (12)0.0007 (11)0.0116 (12)
C400.0272 (14)0.0472 (16)0.0345 (15)0.0008 (12)0.0007 (11)0.0159 (12)
C410.0332 (16)0.0460 (16)0.0413 (17)0.0016 (12)0.0027 (12)0.0148 (13)
C420.0280 (15)0.0523 (18)0.0419 (17)0.0056 (12)0.0020 (12)0.0161 (13)
Cu10.0413 (2)0.0517 (2)0.0292 (2)0.01521 (17)0.00105 (15)0.01773 (16)
Cu20.0268 (2)0.0546 (2)0.0305 (2)0.00206 (15)0.00655 (14)0.01701 (16)
N10.0422 (15)0.0626 (16)0.0316 (13)0.0127 (12)0.0023 (11)0.0171 (12)
N20.0415 (15)0.0582 (16)0.0287 (13)0.0114 (12)0.0035 (10)0.0067 (11)
N30.0267 (12)0.0477 (14)0.0354 (13)0.0000 (10)0.0042 (9)0.0165 (10)
N40.0280 (12)0.0414 (13)0.0321 (12)0.0008 (10)0.0017 (9)0.0134 (10)
O10.0705 (17)0.0769 (17)0.0362 (12)0.0332 (13)0.0009 (11)0.0268 (11)
O20.0611 (17)0.095 (2)0.0673 (17)0.0254 (15)0.0315 (13)0.0527 (16)
O30.0403 (13)0.0937 (18)0.0354 (12)0.0316 (12)0.0034 (9)0.0157 (12)
O40.0332 (11)0.0493 (12)0.0383 (11)0.0068 (9)0.0030 (8)0.0116 (9)
O50.0313 (11)0.0642 (14)0.0353 (11)0.0047 (9)0.0076 (8)0.0092 (10)
O60.0296 (11)0.0755 (15)0.0342 (11)0.0003 (10)0.0041 (8)0.0220 (10)
O70.0334 (12)0.120 (2)0.0390 (13)0.0023 (12)0.0057 (9)0.0368 (13)
O80.0307 (12)0.1060 (19)0.0599 (15)0.0122 (12)0.0014 (10)0.0575 (14)
O90.0435 (12)0.0454 (12)0.0305 (10)0.0086 (9)0.0010 (8)0.0152 (8)
O100.0687 (16)0.0641 (15)0.0375 (12)0.0072 (12)0.0200 (11)0.0166 (11)
O1W0.0392 (13)0.0821 (16)0.0387 (12)0.0018 (12)0.0085 (10)0.0328 (12)
S10.0453 (5)0.1105 (8)0.0299 (4)0.0271 (5)0.0026 (3)0.0094 (4)
S20.0390 (5)0.1057 (7)0.0367 (4)0.0212 (5)0.0039 (3)0.0304 (5)
Geometric parameters (Å, º) top
C1—O21.240 (4)C25—C281.499 (4)
C1—O21.240 (4)C26—C271.377 (4)
C1—O11.267 (4)C26—H260.9300
C1—C21.515 (4)C27—H270.9300
C2—C31.376 (5)C28—O101.230 (4)
C2—C71.387 (5)C28—O91.299 (4)
C3—C41.387 (4)C29—N11.314 (4)
C3—H30.9300C29—N21.345 (4)
C4—C51.378 (5)C29—H290.9300
C4—H40.9300C30—C311.331 (5)
C5—C61.384 (5)C30—N11.372 (4)
C5—O31.395 (4)C30—H300.9300
C6—C71.391 (4)C31—N21.376 (4)
C6—H60.9300C31—H310.9300
C7—H70.9300C32—C331.340 (5)
C8—C91.381 (4)C32—N21.411 (4)
C8—C131.383 (4)C32—S11.704 (3)
C8—O31.388 (3)C33—C341.416 (6)
C9—C101.375 (4)C33—H330.9300
C9—H90.9300C34—C351.331 (5)
C10—C111.386 (4)C34—H340.9300
C10—H100.9300C35—C361.463 (4)
C11—C121.395 (4)C35—S11.703 (3)
C11—C141.490 (4)C36—C371.326 (5)
C12—C131.378 (4)C36—S21.723 (3)
C12—H120.9300C37—C381.415 (5)
C13—H130.9300C37—H370.9300
C14—O41.250 (3)C38—C391.336 (4)
C14—O51.272 (3)C38—H380.9300
C15—O71.239 (4)C39—N41.420 (3)
C15—O71.239 (4)C39—S21.710 (3)
C15—O61.285 (4)C40—N31.320 (3)
C15—C161.503 (4)C40—N41.346 (3)
C16—C211.377 (4)C40—H400.9300
C16—C171.388 (4)C41—C421.340 (4)
C17—C181.375 (4)C41—N31.377 (4)
C17—H170.9300C41—H410.9300
C18—C191.364 (4)C42—N41.388 (4)
C18—H180.9300C42—H420.9300
C19—C201.376 (4)Cu1—O11.925 (2)
C19—O81.387 (3)Cu1—O9i1.967 (2)
C20—C211.386 (4)Cu1—O4ii1.975 (2)
C20—H200.9300Cu1—N11.987 (3)
C21—H210.9300Cu1—O1W2.598 (3)
C22—C271.380 (4)Cu2—O5ii1.935 (2)
C22—C231.385 (5)Cu2—O61.951 (2)
C22—O81.388 (3)Cu2—O1W1.978 (2)
C23—C241.395 (4)Cu2—N3i1.996 (2)
C23—H230.9300Cu2—O9i2.323 (2)
C24—C251.388 (4)O1W—H1W0.8500 (11)
C24—H240.9300O1W—H2W0.8500 (11)
C25—C261.384 (4)
O2—C1—O1125.3 (3)N2—C29—H29124.3
O2—C1—O1125.3 (3)C31—C30—N1109.7 (3)
O2—C1—C2119.3 (3)C31—C30—H30125.1
O2—C1—C2119.3 (3)N1—C30—H30125.1
O1—C1—C2115.4 (3)C30—C31—N2107.0 (3)
C3—C2—C7119.4 (3)C30—C31—H31126.5
C3—C2—C1121.0 (3)N2—C31—H31126.5
C7—C2—C1119.6 (3)C33—C32—N2126.4 (3)
C2—C3—C4120.5 (3)C33—C32—S1110.6 (3)
C2—C3—H3119.7N2—C32—S1123.0 (2)
C4—C3—H3119.7C32—C33—C34111.9 (3)
C5—C4—C3119.5 (3)C32—C33—H33124.1
C5—C4—H4120.3C34—C33—H33124.1
C3—C4—H4120.3C35—C34—C33114.9 (4)
C4—C5—C6121.2 (3)C35—C34—H34122.6
C4—C5—O3117.7 (3)C33—C34—H34122.6
C6—C5—O3120.8 (3)C34—C35—C36125.9 (3)
C5—C6—C7118.5 (3)C34—C35—S1109.3 (3)
C5—C6—H6120.7C36—C35—S1124.6 (2)
C7—C6—H6120.7C37—C36—C35125.1 (3)
C2—C7—C6120.9 (3)C37—C36—S2110.0 (2)
C2—C7—H7119.5C35—C36—S2124.8 (2)
C6—C7—H7119.5C36—C37—C38114.9 (3)
C9—C8—C13120.4 (3)C36—C37—H37122.5
C9—C8—O3115.0 (3)C38—C37—H37122.5
C13—C8—O3124.6 (3)C39—C38—C37111.3 (3)
C10—C9—C8119.7 (3)C39—C38—H38124.3
C10—C9—H9120.1C37—C38—H38124.3
C8—C9—H9120.1C38—C39—N4125.2 (3)
C9—C10—C11121.1 (3)C38—C39—S2112.0 (2)
C9—C10—H10119.5N4—C39—S2122.7 (2)
C11—C10—H10119.5N3—C40—N4111.2 (2)
C10—C11—C12118.3 (3)N3—C40—H40124.4
C10—C11—C14121.9 (3)N4—C40—H40124.4
C12—C11—C14119.8 (3)C42—C41—N3110.1 (3)
C13—C12—C11121.1 (3)C42—C41—H41124.9
C13—C12—H12119.5N3—C41—H41124.9
C11—C12—H12119.5C41—C42—N4106.1 (2)
C12—C13—C8119.3 (3)C41—C42—H42126.9
C12—C13—H13120.3N4—C42—H42126.9
C8—C13—H13120.3O1—Cu1—O9i175.80 (11)
O4—C14—O5126.2 (3)O1—Cu1—O4ii85.72 (9)
O4—C14—C11117.7 (2)O9i—Cu1—O4ii95.29 (8)
O5—C14—C11116.1 (3)O1—Cu1—N189.75 (10)
O7—C15—O6125.5 (3)O9i—Cu1—N189.91 (9)
O7—C15—O6125.5 (3)O4ii—Cu1—N1169.54 (10)
O7—C15—C16119.1 (3)O1—Cu1—O1W97.75 (10)
O7—C15—C16119.1 (3)O9i—Cu1—O1W78.33 (8)
O6—C15—C16115.4 (2)O4ii—Cu1—O1W83.51 (8)
C21—C16—C17118.0 (3)N1—Cu1—O1W106.46 (10)
C21—C16—C15122.2 (3)O5ii—Cu2—O6172.08 (9)
C17—C16—C15119.8 (3)O5ii—Cu2—O1W90.85 (9)
C18—C17—C16121.3 (3)O6—Cu2—O1W91.14 (9)
C18—C17—H17119.4O5ii—Cu2—N3i88.28 (9)
C16—C17—H17119.4O6—Cu2—N3i88.15 (9)
C19—C18—C17119.5 (3)O1W—Cu2—N3i167.78 (10)
C19—C18—H18120.2O5ii—Cu2—O9i95.58 (8)
C17—C18—H18120.2O6—Cu2—O9i92.22 (9)
C18—C19—C20121.0 (3)O1W—Cu2—O9i85.28 (9)
C18—C19—O8116.0 (3)N3i—Cu2—O9i106.94 (9)
C20—C19—O8122.8 (3)C29—N1—C30105.7 (3)
C19—C20—C21119.0 (3)C29—N1—Cu1128.0 (2)
C19—C20—H20120.5C30—N1—Cu1125.7 (2)
C21—C20—H20120.5C29—N2—C31106.2 (3)
C16—C21—C20121.3 (3)C29—N2—C32127.3 (3)
C16—C21—H21119.4C31—N2—C32126.5 (3)
C20—C21—H21119.4C40—N3—C41105.7 (2)
C27—C22—C23121.2 (3)C40—N3—Cu2i127.48 (19)
C27—C22—O8114.9 (3)C41—N3—Cu2i126.77 (19)
C23—C22—O8123.4 (3)C40—N4—C42106.8 (2)
C22—C23—C24118.7 (3)C40—N4—C39127.8 (2)
C22—C23—H23120.7C42—N4—C39125.3 (2)
C24—C23—H23120.7C1—O1—Cu1120.5 (2)
C25—C24—C23120.5 (3)C8—O3—C5120.0 (2)
C25—C24—H24119.7C14—O4—Cu1ii133.35 (19)
C23—C24—H24119.7C14—O5—Cu2ii128.36 (19)
C26—C25—C24119.3 (3)C15—O6—Cu2128.00 (18)
C26—C25—C28118.7 (3)C19—O8—C22121.3 (2)
C24—C25—C28122.0 (3)C28—O9—Cu1i105.95 (17)
C27—C26—C25120.8 (3)C28—O9—Cu2i139.72 (17)
C27—C26—H26119.6Cu1i—O9—Cu2i97.17 (8)
C25—C26—H26119.6Cu2—O1W—Cu188.58 (9)
C26—C27—C22119.5 (3)Cu2—O1W—H1W140.0 (17)
C26—C27—H27120.3Cu1—O1W—H1W75 (2)
C22—C27—H27120.3Cu2—O1W—H2W113.9 (17)
O10—C28—O9122.0 (3)Cu1—O1W—H2W102 (3)
O10—C28—C25120.7 (3)H1W—O1W—H2W105.14 (18)
O9—C28—C25117.2 (3)C35—S1—C3293.20 (15)
N1—C29—N2111.4 (3)C39—S2—C3691.64 (14)
N1—C29—H29124.3
O2—C1—C2—C3174.6 (3)S1—C35—C36—C37163.5 (4)
O2—C1—C2—C3174.6 (3)C34—C35—C36—S2164.5 (5)
O1—C1—C2—C34.7 (4)S1—C35—C36—S221.7 (5)
O2—C1—C2—C73.8 (5)C35—C36—C37—C38175.4 (4)
O2—C1—C2—C73.8 (5)S2—C36—C37—C380.0 (6)
O1—C1—C2—C7176.8 (3)C36—C37—C38—C391.9 (7)
C7—C2—C3—C40.8 (5)C37—C38—C39—N4176.6 (4)
C1—C2—C3—C4179.3 (3)C37—C38—C39—S22.9 (6)
C2—C3—C4—C50.6 (5)N3—C41—C42—N40.7 (3)
C3—C4—C5—C61.9 (5)N2—C29—N1—C300.4 (4)
C3—C4—C5—O3176.1 (3)N2—C29—N1—Cu1171.5 (2)
C4—C5—C6—C71.6 (5)C31—C30—N1—C291.4 (5)
O3—C5—C6—C7175.7 (3)C31—C30—N1—Cu1170.7 (3)
C3—C2—C7—C61.1 (5)N1—C29—N2—C310.7 (4)
C1—C2—C7—C6179.6 (3)N1—C29—N2—C32178.1 (3)
C5—C6—C7—C20.1 (5)C30—C31—N2—C291.5 (4)
C13—C8—C9—C101.8 (5)C30—C31—N2—C32177.3 (3)
O3—C8—C9—C10175.9 (3)C33—C32—N2—C29162.1 (5)
C8—C9—C10—C112.9 (5)S1—C32—N2—C2915.9 (5)
C9—C10—C11—C121.4 (5)C33—C32—N2—C3116.5 (7)
C9—C10—C11—C14179.8 (3)S1—C32—N2—C31165.5 (3)
C10—C11—C12—C131.3 (5)N4—C40—N3—C410.5 (3)
C14—C11—C12—C13177.1 (3)N4—C40—N3—Cu2i178.42 (18)
C11—C12—C13—C82.4 (6)C42—C41—N3—C400.2 (3)
C9—C8—C13—C120.9 (6)C42—C41—N3—Cu2i177.8 (2)
O3—C8—C13—C12178.3 (3)N3—C40—N4—C420.9 (3)
C10—C11—C14—O4143.3 (3)N3—C40—N4—C39175.7 (3)
C12—C11—C14—O438.4 (4)C41—C42—N4—C401.0 (3)
C10—C11—C14—O537.1 (4)C41—C42—N4—C39175.7 (3)
C12—C11—C14—O5141.2 (3)C38—C39—N4—C40179.7 (4)
O7—C15—C16—C21172.2 (3)S2—C39—N4—C400.2 (4)
O7—C15—C16—C21172.2 (3)C38—C39—N4—C423.7 (5)
O6—C15—C16—C218.5 (4)S2—C39—N4—C42175.8 (2)
O7—C15—C16—C176.8 (5)O2—C1—O1—Cu123.6 (5)
O7—C15—C16—C176.8 (5)O2—C1—O1—Cu123.6 (5)
O6—C15—C16—C17172.5 (3)C2—C1—O1—Cu1157.2 (2)
C21—C16—C17—C180.1 (5)O1—C1—O2—O20.0 (3)
C15—C16—C17—C18179.2 (3)C2—C1—O2—O20.0 (3)
C16—C17—C18—C190.6 (5)C9—C8—O3—C5169.2 (3)
C17—C18—C19—C200.5 (5)C13—C8—O3—C513.2 (5)
C17—C18—C19—O8174.1 (3)C4—C5—O3—C8129.1 (3)
C18—C19—C20—C210.1 (5)C6—C5—O3—C856.6 (4)
O8—C19—C20—C21174.1 (3)O5—C14—O4—Cu1ii14.5 (5)
C17—C16—C21—C200.3 (5)C11—C14—O4—Cu1ii165.13 (19)
C15—C16—C21—C20178.7 (3)O4—C14—O5—Cu2ii11.7 (4)
C19—C20—C21—C160.4 (6)C11—C14—O5—Cu2ii167.92 (19)
C27—C22—C23—C240.5 (5)O7—C15—O6—Cu217.3 (5)
O8—C22—C23—C24170.6 (3)O7—C15—O6—Cu217.3 (5)
C22—C23—C24—C250.1 (5)C16—C15—O6—Cu2161.86 (19)
C23—C24—C25—C261.1 (4)O6—C15—O7—O70.0 (11)
C23—C24—C25—C28178.0 (3)C16—C15—O7—O70.0 (9)
C24—C25—C26—C272.0 (4)C18—C19—O8—C22151.0 (3)
C28—C25—C26—C27177.2 (3)C20—C19—O8—C2234.6 (5)
C25—C26—C27—C221.6 (5)C27—C22—O8—C19143.5 (3)
C23—C22—C27—C260.4 (5)C23—C22—O8—C1944.9 (5)
O8—C22—C27—C26172.2 (3)O10—C28—O9—Cu1i8.2 (3)
C26—C25—C28—O1015.1 (4)C25—C28—O9—Cu1i169.40 (19)
C24—C25—C28—O10165.7 (3)O10—C28—O9—Cu2i114.4 (3)
C26—C25—C28—O9167.3 (3)C25—C28—O9—Cu2i68.1 (4)
C24—C25—C28—O911.9 (4)C34—C35—S1—C323.8 (4)
N1—C30—C31—N21.8 (5)C36—C35—S1—C32178.5 (3)
N2—C32—C33—C34178.5 (5)C33—C32—S1—C352.4 (4)
S1—C32—C33—C340.3 (7)N2—C32—S1—C35179.4 (3)
C32—C33—C34—C352.7 (10)C38—C39—S2—C362.5 (3)
C33—C34—C35—C36178.9 (5)N4—C39—S2—C36177.0 (2)
C33—C34—C35—S14.4 (8)C37—C36—S2—C391.4 (3)
C34—C35—C36—C3710.3 (8)C35—C36—S2—C39176.9 (3)
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+3, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O20.85 (1)1.76 (1)2.611 (3)174 (3)
O1W—H2W···O70.85 (1)1.80 (2)2.554 (3)147 (3)
C30—H30···O10iii0.932.353.192 (4)150
Symmetry code: (iii) x+1, y, z1.
 

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