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Three coordination complexes with CuI centres have been prepared using the symmetrical flexible organic ligands 1,3-bis­{[5-(quinolin-2-yl)-1,3,4-oxa­diazol-2-yl]sulfan­yl}propane (L1) and 1,4-bis­{[5-(quinolin-2-yl)-1,3,4-oxa­diazol-2-yl]sulfan­yl}butane (L2). Crystallization of L1 with Cu(SO3CF3)2 and of L2 with Cu(BF4)2 and Cu(ClO4)2 in a CH2Cl2/CH3OH mixed-solvent system at room temperature afforded the coordination complexes catena-poly[[copper(I)-μ-1,3-bis­{[5-(quinolin-2-yl)-1,3,4-oxa­diazol-2-yl]sulfanyl}propane] methanesulfonate di­chloro­methane 0.6-solvate], {[Cu(C25H18N6O2S2)](CF3SO3)·0.6CH2Cl2}n, (I), bis­(μ-1,4-bis­{[5-(quinolin-2-yl)-1,3,4-oxa­diazol-2-yl]sulfanyl}butane)­dicopper(I) bis­(tetra­fluorido­borate)–di­chloro­methane–methanol (1/1.5/1), [Cu2(C26H20N6O2S2)2](BF4)2·1.5CH2Cl2·CH3OH, (II), and bis­(μ-1,4-bis­{[5-(quinolin-2-yl)-1,3,4-oxa­diazol-2-yl]sulfanyl}butane)­dicopper(I) bis­(perchlorate)–di­chloro­methane–methanol (1/2/1), [Cu2(C26H20N6O2S2)2](ClO4)2·2CH2Cl2·CH3OH, (III). Under the control of the dumbbell-shaped CF3SO3 anion, complex (I) forms a one-dimensional chain and neighbouring chains form a spiral double chain. Under the control of the regular tetra­hedron-shaped BF4 and ClO4 anions, complexes (II) and (III) have been obtained as bimetallic rings, which further inter­act via π–π inter­actions to form two-dimensional networks. The anions play a decisive role in determining the arrangement of these discrete mol­ecular complexes in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615012929/wq3091sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012929/wq3091Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012929/wq3091IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012929/wq3091IIIsup4.hkl
Contains datablock III

CCDC references: 1410674; 1410673; 1410672

Computing details top

For all compounds, data collection: (CrysAlis PRO; Agilent, 2013); cell refinement: (CrysAlis PRO; Agilent, 2013); data reduction: (CrysAlis PRO; Agilent, 2013); 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 (Sheldrick, 2008).

(I) catena-Poly[[copper(I)-µ-1,3-bis{[5-(quinolin-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}propane] methanesulfonate dichloromethane 0.6-solvate] top
Crystal data top
[Cu(C25H18N6O2S2)](CF3SO3)·0.6CH2Cl2F(000) = 3082
Mr = 762.14Dx = 1.620 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
a = 16.4083 (9) ÅCell parameters from 5497 reflections
b = 17.639 (2) Åθ = 3.7–28.4°
c = 21.6604 (13) ŵ = 1.07 mm1
β = 94.477 (6)°T = 100 K
V = 6250.1 (9) Å3Block, clear light red
Z = 80.10 × 0.07 × 0.05 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Eos detector
6389 independent reflections
Radiation source: SuperNova (Mo) X-ray Source4855 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.036
Detector resolution: 16.0793 pixels mm-1θmax = 26.4°, θmin = 3.0°
ω scansh = 2019
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 2220
Tmin = 0.805, Tmax = 1.000l = 2727
19669 measured reflections
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0785P)2 + 19.968P]
where P = (Fo2 + 2Fc2)/3
6389 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 1.12 e Å3
0 restraintsΔρmin = 0.43 e Å3
Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/UeqOcc. (<1)
C10.0315 (2)0.6238 (2)0.64414 (18)0.0283 (8)
C20.0416 (2)0.7027 (2)0.64602 (19)0.0345 (9)
H20.01710.73330.61780.041*
C30.0873 (3)0.7348 (3)0.6892 (2)0.0396 (10)
H30.09340.78720.69020.047*
C40.1252 (3)0.6897 (3)0.73216 (19)0.0385 (10)
H40.15610.71260.76120.046*
C50.1171 (2)0.6123 (3)0.73161 (19)0.0356 (9)
H50.14260.58290.76010.043*
C60.0697 (2)0.5768 (2)0.68752 (18)0.0307 (9)
C70.0583 (2)0.4976 (2)0.68532 (18)0.0327 (9)
H70.08390.46600.71230.039*
C80.0094 (2)0.4677 (2)0.64322 (18)0.0308 (9)
H80.00000.41580.64170.037*
C90.0267 (2)0.5177 (2)0.60201 (18)0.0272 (8)
C100.0794 (2)0.4922 (2)0.55591 (18)0.0277 (8)
C110.1519 (2)0.4229 (2)0.50228 (18)0.0299 (8)
C120.2504 (3)0.3709 (3)0.41701 (19)0.0363 (10)
H12A0.21470.39330.38420.044*
H12B0.29050.40840.43200.044*
C130.2924 (3)0.3009 (3)0.3938 (2)0.0378 (10)
H13A0.32490.27790.42820.045*
H13B0.25100.26450.37920.045*
C140.3469 (3)0.3168 (3)0.3424 (2)0.0424 (11)
H14A0.31430.34040.30840.051*
H14B0.36670.26890.32750.051*
C150.4877 (3)0.3178 (3)0.41623 (19)0.0366 (10)
C160.5819 (2)0.2907 (2)0.48572 (19)0.0325 (9)
C170.6537 (2)0.2945 (2)0.52948 (18)0.0313 (9)
C180.7030 (3)0.3595 (2)0.5387 (2)0.0370 (10)
H180.69070.40410.51700.044*
C190.7696 (3)0.3549 (2)0.5806 (2)0.0390 (10)
H190.80320.39690.58800.047*
C200.7873 (3)0.2867 (2)0.61261 (18)0.0339 (9)
C210.8558 (3)0.2775 (3)0.65626 (19)0.0403 (11)
H210.89020.31850.66580.048*
C220.8717 (3)0.2093 (3)0.68438 (19)0.0414 (11)
H220.91730.20390.71240.050*
C230.8192 (3)0.1464 (3)0.6711 (2)0.0389 (10)
H230.83080.10000.69020.047*
C240.7518 (2)0.1539 (2)0.63057 (18)0.0323 (9)
H240.71700.11280.62280.039*
C250.7344 (2)0.2237 (2)0.60031 (17)0.0305 (9)
C260.2043 (3)0.0684 (3)0.2419 (2)0.0450 (11)
Cu10.08010 (3)0.64655 (3)0.53552 (2)0.03214 (17)
F20.13753 (17)0.03386 (19)0.25902 (14)0.0605 (8)
F30.2366 (2)0.02553 (19)0.19965 (13)0.0639 (9)
F10.17975 (18)0.13373 (17)0.21422 (13)0.0558 (8)
N10.01596 (18)0.59258 (18)0.60146 (14)0.0272 (7)
N20.11272 (19)0.53696 (18)0.51713 (15)0.0278 (7)
N30.1610 (2)0.49120 (19)0.48135 (15)0.0303 (7)
N50.53763 (19)0.23046 (19)0.47625 (15)0.0309 (7)
N40.4745 (2)0.2478 (2)0.43043 (16)0.0355 (8)
N60.66716 (19)0.22884 (19)0.55879 (15)0.0293 (7)
O10.10084 (16)0.41860 (15)0.54919 (12)0.0306 (6)
O20.55465 (18)0.34928 (16)0.44887 (14)0.0367 (7)
O40.3441 (2)0.1240 (2)0.28194 (16)0.0497 (8)
O50.2958 (2)0.01170 (18)0.33211 (15)0.0446 (8)
O30.2312 (2)0.1334 (2)0.34759 (16)0.0524 (9)
S30.19173 (7)0.33790 (6)0.47979 (5)0.0388 (3)
S20.43429 (7)0.37731 (7)0.36357 (6)0.0441 (3)
S10.27757 (7)0.08669 (6)0.30868 (5)0.0375 (3)
C270.4216 (5)0.4481 (5)0.5928 (5)0.054 (2)0.40
H27A0.37660.41830.60620.065*0.40
H27B0.41650.49880.60930.065*0.40
Cl10.51537 (14)0.40773 (13)0.62610 (11)0.0602 (6)0.40
Cl20.41209 (19)0.45324 (19)0.51679 (12)0.0493 (7)0.40
C27'0.4216 (5)0.4481 (5)0.5928 (5)0.054 (2)0.20
H27C0.38170.45610.62290.065*0.20
H27D0.42990.49440.56990.065*0.20
Cl1'0.51537 (14)0.40773 (13)0.62610 (11)0.0602 (6)0.20
Cl2'0.3989 (4)0.3701 (5)0.5448 (3)0.068 (2)0.20
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0244 (18)0.024 (2)0.038 (2)0.0023 (16)0.0071 (16)0.0019 (16)
C20.036 (2)0.026 (2)0.043 (2)0.0012 (18)0.0124 (18)0.0056 (18)
C30.040 (2)0.030 (2)0.050 (2)0.002 (2)0.0138 (19)0.0027 (19)
C40.036 (2)0.041 (3)0.040 (2)0.004 (2)0.0136 (18)0.0009 (19)
C50.033 (2)0.037 (3)0.038 (2)0.0054 (19)0.0110 (17)0.0035 (19)
C60.0251 (19)0.032 (2)0.036 (2)0.0047 (17)0.0073 (16)0.0047 (17)
C70.030 (2)0.031 (2)0.038 (2)0.0069 (18)0.0065 (16)0.0105 (17)
C80.029 (2)0.022 (2)0.042 (2)0.0038 (17)0.0065 (17)0.0061 (17)
C90.0251 (18)0.020 (2)0.0366 (19)0.0041 (16)0.0061 (15)0.0040 (16)
C100.0268 (19)0.018 (2)0.039 (2)0.0007 (16)0.0048 (16)0.0026 (16)
C110.036 (2)0.020 (2)0.035 (2)0.0001 (17)0.0080 (16)0.0006 (16)
C120.043 (2)0.027 (2)0.040 (2)0.0033 (19)0.0127 (18)0.0024 (18)
C130.042 (2)0.028 (2)0.045 (2)0.0006 (19)0.0076 (19)0.0006 (18)
C140.050 (3)0.036 (3)0.041 (2)0.009 (2)0.008 (2)0.001 (2)
C150.039 (2)0.029 (2)0.044 (2)0.0043 (19)0.0164 (19)0.0073 (18)
C160.039 (2)0.019 (2)0.042 (2)0.0006 (18)0.0197 (18)0.0058 (17)
C170.040 (2)0.021 (2)0.036 (2)0.0005 (17)0.0203 (17)0.0004 (16)
C180.051 (3)0.020 (2)0.042 (2)0.0044 (19)0.021 (2)0.0025 (17)
C190.054 (3)0.024 (2)0.042 (2)0.014 (2)0.022 (2)0.0061 (18)
C200.041 (2)0.029 (2)0.035 (2)0.0062 (19)0.0209 (18)0.0045 (17)
C210.045 (2)0.038 (3)0.040 (2)0.016 (2)0.0175 (19)0.0079 (19)
C220.042 (2)0.047 (3)0.036 (2)0.005 (2)0.0099 (18)0.004 (2)
C230.044 (2)0.033 (3)0.042 (2)0.004 (2)0.0166 (19)0.0003 (19)
C240.037 (2)0.024 (2)0.038 (2)0.0069 (18)0.0142 (17)0.0010 (16)
C250.037 (2)0.024 (2)0.0332 (19)0.0031 (17)0.0205 (17)0.0026 (16)
C260.049 (3)0.035 (3)0.052 (3)0.009 (2)0.013 (2)0.005 (2)
Cu10.0355 (3)0.0168 (3)0.0459 (3)0.0023 (2)0.0147 (2)0.0060 (2)
F20.0525 (17)0.063 (2)0.0649 (18)0.0121 (15)0.0005 (14)0.0120 (15)
F30.081 (2)0.060 (2)0.0509 (16)0.0222 (17)0.0042 (15)0.0134 (14)
F10.0624 (18)0.0471 (18)0.0587 (17)0.0150 (15)0.0093 (14)0.0121 (14)
N10.0243 (16)0.0215 (18)0.0364 (17)0.0023 (14)0.0068 (13)0.0026 (13)
N20.0273 (16)0.0183 (17)0.0389 (17)0.0005 (13)0.0110 (14)0.0017 (13)
N30.0365 (18)0.0194 (18)0.0367 (17)0.0027 (14)0.0128 (14)0.0014 (14)
N50.0325 (17)0.0224 (18)0.0397 (18)0.0022 (14)0.0153 (14)0.0057 (14)
N40.0351 (18)0.0253 (19)0.048 (2)0.0009 (15)0.0127 (15)0.0081 (15)
N60.0340 (17)0.0196 (17)0.0370 (17)0.0026 (14)0.0191 (14)0.0001 (13)
O10.0372 (15)0.0169 (14)0.0392 (15)0.0029 (12)0.0116 (12)0.0042 (11)
O20.0442 (17)0.0211 (16)0.0464 (16)0.0004 (13)0.0147 (13)0.0064 (12)
O40.0508 (19)0.037 (2)0.063 (2)0.0019 (16)0.0172 (16)0.0071 (16)
O50.0569 (19)0.0268 (17)0.0504 (18)0.0023 (15)0.0051 (15)0.0037 (14)
O30.057 (2)0.042 (2)0.060 (2)0.0087 (17)0.0156 (17)0.0102 (16)
S30.0546 (7)0.0206 (5)0.0434 (6)0.0070 (5)0.0176 (5)0.0039 (4)
S20.0463 (6)0.0326 (7)0.0552 (7)0.0061 (5)0.0158 (5)0.0170 (5)
S10.0432 (6)0.0234 (6)0.0471 (6)0.0031 (5)0.0121 (5)0.0002 (4)
C270.046 (5)0.027 (4)0.091 (6)0.009 (4)0.017 (4)0.011 (4)
Cl10.0572 (13)0.0475 (13)0.0741 (14)0.0047 (10)0.0052 (11)0.0160 (11)
Cl20.0547 (17)0.060 (2)0.0329 (13)0.0178 (15)0.0012 (12)0.0099 (13)
C27'0.046 (5)0.027 (4)0.091 (6)0.009 (4)0.017 (4)0.011 (4)
Cl1'0.0572 (13)0.0475 (13)0.0741 (14)0.0047 (10)0.0052 (11)0.0160 (11)
Cl2'0.058 (4)0.078 (5)0.066 (4)0.020 (4)0.001 (3)0.015 (4)
Geometric parameters (Å, º) top
C1—N11.370 (5)C16—C171.454 (6)
C1—C21.403 (6)C17—N61.331 (5)
C1—C61.433 (5)C17—C181.409 (6)
C2—C31.367 (6)C18—C191.368 (7)
C2—H20.9300C18—H180.9300
C3—C41.405 (6)C19—C201.407 (6)
C3—H30.9300C19—H190.9300
C4—C51.373 (7)C20—C211.421 (6)
C4—H40.9300C20—C251.422 (6)
C5—C61.422 (6)C21—C221.365 (7)
C5—H50.9300C21—H210.9300
C6—C71.411 (6)C22—C231.420 (6)
C7—C81.366 (6)C22—H220.9300
C7—H70.9300C23—C241.364 (6)
C8—C91.417 (5)C23—H230.9300
C8—H80.9300C24—C251.414 (6)
C9—N11.332 (5)C24—H240.9300
C9—C101.444 (5)C25—N61.371 (5)
C10—N21.304 (5)C26—F31.329 (5)
C10—O11.356 (5)C26—F21.331 (5)
C11—N31.300 (5)C26—F11.346 (5)
C11—O11.368 (5)C26—S11.836 (5)
C11—S31.721 (4)Cu1—N5i2.046 (3)
C12—C131.519 (6)Cu1—N22.053 (3)
C12—S31.822 (4)Cu1—N12.071 (3)
C12—H12A0.9700Cu1—N6i2.071 (3)
C12—H12B0.9700N2—N31.405 (4)
C13—C141.508 (6)N5—N41.411 (5)
C13—H13A0.9700N5—Cu1ii2.046 (3)
C13—H13B0.9700N6—Cu1ii2.071 (3)
C14—S21.818 (5)O4—S11.435 (3)
C14—H14A0.9700O5—S11.440 (3)
C14—H14B0.9700O3—S11.438 (3)
C15—N41.295 (6)C27—Cl21.644 (10)
C15—O21.376 (5)C27—Cl11.794 (9)
C15—S21.736 (4)C27—H27A0.9700
C16—N51.294 (5)C27—H27B0.9700
C16—O21.360 (5)
N1—C1—C2119.5 (4)C18—C19—C20120.1 (4)
N1—C1—C6120.7 (4)C18—C19—H19120.0
C2—C1—C6119.7 (4)C20—C19—H19120.0
C3—C2—C1120.2 (4)C19—C20—C21123.2 (4)
C3—C2—H2119.9C19—C20—C25118.4 (4)
C1—C2—H2119.9C21—C20—C25118.4 (4)
C2—C3—C4120.9 (4)C22—C21—C20120.7 (4)
C2—C3—H3119.6C22—C21—H21119.6
C4—C3—H3119.6C20—C21—H21119.6
C5—C4—C3120.6 (4)C21—C22—C23120.5 (4)
C5—C4—H4119.7C21—C22—H22119.8
C3—C4—H4119.7C23—C22—H22119.8
C4—C5—C6120.1 (4)C24—C23—C22120.2 (4)
C4—C5—H5119.9C24—C23—H23119.9
C6—C5—H5119.9C22—C23—H23119.9
C7—C6—C5122.6 (4)C23—C24—C25120.5 (4)
C7—C6—C1119.0 (4)C23—C24—H24119.8
C5—C6—C1118.4 (4)C25—C24—H24119.8
C8—C7—C6119.4 (4)N6—C25—C24119.0 (4)
C8—C7—H7120.3N6—C25—C20121.3 (4)
C6—C7—H7120.3C24—C25—C20119.7 (4)
C7—C8—C9118.4 (4)F3—C26—F2108.2 (4)
C7—C8—H8120.8F3—C26—F1107.6 (4)
C9—C8—H8120.8F2—C26—F1107.0 (4)
N1—C9—C8124.1 (4)F3—C26—S1111.7 (3)
N1—C9—C10112.9 (3)F2—C26—S1111.3 (3)
C8—C9—C10123.0 (4)F1—C26—S1110.8 (4)
N2—C10—O1112.7 (3)N5i—Cu1—N2129.84 (13)
N2—C10—C9124.1 (4)N5i—Cu1—N1126.79 (12)
O1—C10—C9123.2 (3)N2—Cu1—N181.67 (13)
N3—C11—O1113.8 (3)N5i—Cu1—N6i80.81 (14)
N3—C11—S3130.7 (3)N2—Cu1—N6i121.46 (13)
O1—C11—S3115.5 (3)N1—Cu1—N6i122.16 (12)
C13—C12—S3105.5 (3)C9—N1—C1118.3 (3)
C13—C12—H12A110.6C9—N1—Cu1112.8 (2)
S3—C12—H12A110.6C1—N1—Cu1128.8 (3)
C13—C12—H12B110.6C10—N2—N3106.8 (3)
S3—C12—H12B110.6C10—N2—Cu1108.5 (3)
H12A—C12—H12B108.8N3—N2—Cu1144.5 (2)
C14—C13—C12113.8 (4)C11—N3—N2104.8 (3)
C14—C13—H13A108.8C16—N5—N4107.8 (3)
C12—C13—H13A108.8C16—N5—Cu1ii109.5 (3)
C14—C13—H13B108.8N4—N5—Cu1ii142.5 (3)
C12—C13—H13B108.8C15—N4—N5104.3 (3)
H13A—C13—H13B107.7C17—N6—C25117.7 (3)
C13—C14—S2115.1 (3)C17—N6—Cu1ii114.1 (3)
C13—C14—H14A108.5C25—N6—Cu1ii128.2 (3)
S2—C14—H14A108.5C10—O1—C11101.9 (3)
C13—C14—H14B108.5C16—O2—C15102.0 (3)
S2—C14—H14B108.5C11—S3—C1299.7 (2)
H14A—C14—H14B107.5C15—S2—C1499.1 (2)
N4—C15—O2113.8 (4)O4—S1—O3115.4 (2)
N4—C15—S2130.4 (4)O4—S1—O5114.8 (2)
O2—C15—S2115.8 (3)O3—S1—O5115.1 (2)
N5—C16—O2112.1 (4)O4—S1—C26103.6 (2)
N5—C16—C17123.9 (4)O3—S1—C26102.6 (2)
O2—C16—C17124.0 (4)O5—S1—C26102.8 (2)
N6—C17—C18124.7 (4)Cl2—C27—Cl1115.9 (5)
N6—C17—C16111.5 (4)Cl2—C27—H27A108.3
C18—C17—C16123.9 (4)Cl1—C27—H27A108.3
C19—C18—C17117.8 (4)Cl2—C27—H27B108.3
C19—C18—H18121.1Cl1—C27—H27B108.3
C17—C18—H18121.1H27A—C27—H27B107.4
N1—C1—C2—C3178.6 (4)N6i—Cu1—N1—C156.7 (4)
C6—C1—C2—C30.3 (6)O1—C10—N2—N30.4 (4)
C1—C2—C3—C40.3 (7)C9—C10—N2—N3178.4 (3)
C2—C3—C4—C50.0 (7)O1—C10—N2—Cu1177.0 (2)
C3—C4—C5—C60.3 (6)C9—C10—N2—Cu11.8 (5)
C4—C5—C6—C7179.1 (4)N5i—Cu1—N2—C10133.4 (3)
C4—C5—C6—C10.2 (6)N1—Cu1—N2—C101.6 (3)
N1—C1—C6—C70.6 (6)N6i—Cu1—N2—C10121.1 (3)
C2—C1—C6—C7179.5 (4)N5i—Cu1—N2—N352.2 (5)
N1—C1—C6—C5178.8 (3)N1—Cu1—N2—N3176.1 (4)
C2—C1—C6—C50.1 (6)N6i—Cu1—N2—N353.3 (5)
C5—C6—C7—C8177.5 (4)O1—C11—N3—N20.4 (4)
C1—C6—C7—C81.9 (6)S3—C11—N3—N2179.0 (3)
C6—C7—C8—C91.6 (6)C10—N2—N3—C110.0 (4)
C7—C8—C9—N10.1 (6)Cu1—N2—N3—C11174.5 (4)
C7—C8—C9—C10179.8 (4)O2—C16—N5—N40.8 (4)
N1—C9—C10—N20.7 (5)C17—C16—N5—N4179.3 (3)
C8—C9—C10—N2179.4 (4)O2—C16—N5—Cu1ii177.9 (2)
N1—C9—C10—O1178.0 (3)C17—C16—N5—Cu1ii3.6 (5)
C8—C9—C10—O11.9 (6)O2—C15—N4—N50.1 (4)
S3—C12—C13—C14178.2 (3)S2—C15—N4—N5179.6 (3)
C12—C13—C14—S264.0 (5)C16—N5—N4—C150.5 (4)
N5—C16—C17—N60.7 (5)Cu1ii—N5—N4—C15176.1 (3)
O2—C16—C17—N6179.0 (3)C18—C17—N6—C250.9 (5)
N5—C16—C17—C18178.4 (4)C16—C17—N6—C25178.2 (3)
O2—C16—C17—C180.1 (6)C18—C17—N6—Cu1ii178.2 (3)
N6—C17—C18—C190.2 (6)C16—C17—N6—Cu1ii2.6 (4)
C16—C17—C18—C19178.9 (4)C24—C25—N6—C17177.9 (3)
C17—C18—C19—C200.4 (6)C20—C25—N6—C171.1 (5)
C18—C19—C20—C21179.3 (4)C24—C25—N6—Cu1ii3.1 (5)
C18—C19—C20—C250.2 (6)C20—C25—N6—Cu1ii177.9 (3)
C19—C20—C21—C22177.7 (4)N2—C10—O1—C110.6 (4)
C25—C20—C21—C221.8 (6)C9—C10—O1—C11178.3 (4)
C20—C21—C22—C230.9 (6)N3—C11—O1—C100.6 (4)
C21—C22—C23—C240.6 (6)S3—C11—O1—C10179.5 (3)
C22—C23—C24—C251.3 (6)N5—C16—O2—C150.7 (4)
C23—C24—C25—N6178.6 (3)C17—C16—O2—C15179.2 (4)
C23—C24—C25—C200.4 (6)N4—C15—O2—C160.3 (4)
C19—C20—C25—N60.6 (5)S2—C15—O2—C16179.2 (3)
C21—C20—C25—N6179.9 (3)N3—C11—S3—C120.5 (5)
C19—C20—C25—C24178.4 (4)O1—C11—S3—C12178.2 (3)
C21—C20—C25—C241.1 (5)C13—C12—S3—C11177.9 (3)
C8—C9—N1—C11.4 (6)N4—C15—S2—C147.6 (5)
C10—C9—N1—C1178.5 (3)O2—C15—S2—C14171.9 (3)
C8—C9—N1—Cu1179.1 (3)C13—C14—S2—C1565.7 (4)
C10—C9—N1—Cu10.8 (4)F3—C26—S1—O459.3 (4)
C2—C1—N1—C9177.9 (4)F2—C26—S1—O4179.6 (3)
C6—C1—N1—C91.0 (5)F1—C26—S1—O460.7 (4)
C2—C1—N1—Cu10.6 (5)F3—C26—S1—O3179.6 (3)
C6—C1—N1—Cu1178.3 (3)F2—C26—S1—O359.2 (4)
N5i—Cu1—N1—C9135.7 (3)F1—C26—S1—O359.7 (4)
N2—Cu1—N1—C91.4 (3)F3—C26—S1—O560.6 (4)
N6i—Cu1—N1—C9120.7 (3)F2—C26—S1—O560.6 (4)
N5i—Cu1—N1—C146.9 (4)F1—C26—S1—O5179.5 (3)
N2—Cu1—N1—C1178.8 (3)
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1/2, y1/2, z.
(II) Bis(µ-1,4-bis{[5-(quinolin-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}butane)dicopper(I) bis(tetrafluoridoborate)–dichloromethane–methanol (1/1.5/1) top
Crystal data top
[Cu2(C26H20N6O2S2)2](BF4)2·1.5CH2Cl2·CH4OZ = 1
Mr = 1485.33F(000) = 753
Triclinic, P1Dx = 1.559 Mg m3
a = 11.1554 (8) ÅMo Kα radiation, λ = 0.7107 Å
b = 11.5090 (9) ÅCell parameters from 3813 reflections
c = 13.6722 (11) Åθ = 3.6–26.5°
α = 68.550 (8)°µ = 1.01 mm1
β = 81.603 (6)°T = 100 K
γ = 76.089 (6)°Plate, clear light orange
V = 1582.6 (2) Å30.21 × 0.15 × 0.02 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Eos detector
6460 independent reflections
Radiation source: SuperNova (Mo) X-ray Source4665 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.037
Detector resolution: 16.0793 pixels mm-1θmax = 26.4°, θmin = 2.9°
ω scansh = 1313
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1414
Tmin = 0.727, Tmax = 1.000l = 1617
12689 measured reflections
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0997P)2 + 1.9848P]
where P = (Fo2 + 2Fc2)/3
6460 reflections(Δ/σ)max = 0.002
487 parametersΔρmax = 1.43 e Å3
34 restraintsΔρmin = 0.48 e Å3
Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/UeqOcc. (<1)
B10.9522 (8)0.4239 (9)0.1419 (7)0.041 (3)0.50
B20.50001.00001.00000.0326 (16)
C10.0941 (4)1.1288 (4)1.0411 (3)0.0291 (9)
C20.2128 (4)1.1011 (4)1.0727 (4)0.0360 (11)
H20.26971.12141.02270.043*
C30.2443 (5)1.0444 (5)1.1769 (4)0.0439 (12)
H30.32281.02591.19720.053*
C40.1599 (5)1.0134 (5)1.2542 (4)0.0453 (13)
H40.18370.97581.32480.054*
C50.0434 (5)1.0379 (4)1.2265 (4)0.0396 (11)
H50.01181.01671.27800.048*
C60.0068 (4)1.0958 (4)1.1191 (4)0.0334 (10)
C70.1123 (4)1.1214 (4)1.0853 (4)0.0358 (11)
H70.17071.10061.13420.043*
C80.1423 (4)1.1770 (4)0.9802 (4)0.0332 (10)
H80.22061.19500.95650.040*
C90.0517 (4)1.2059 (4)0.9096 (3)0.0296 (9)
C100.0729 (4)1.2651 (4)0.7962 (3)0.0289 (9)
C110.1645 (4)1.3357 (5)0.6468 (4)0.0366 (11)
C120.2231 (5)1.4265 (5)0.4380 (4)0.0472 (13)
H12A0.14321.48190.44180.057*
H12B0.27501.47600.38320.057*
C130.2055 (5)1.3176 (5)0.4077 (4)0.0455 (12)
H13A0.16391.35280.34250.055*
H13B0.15201.26930.46170.055*
C140.3263 (5)1.2267 (5)0.3935 (4)0.0469 (13)
H14A0.38141.27410.34060.056*
H14B0.36691.18760.45920.056*
C150.2996 (5)1.1232 (5)0.3594 (4)0.0477 (13)
H15A0.26341.16150.29170.057*
H15B0.24151.07820.41040.057*
C160.3865 (4)0.9176 (5)0.3029 (4)0.0361 (11)
C170.3920 (4)0.7692 (4)0.2457 (3)0.0331 (10)
C180.4356 (4)0.6592 (4)0.2110 (3)0.0343 (10)
C190.5598 (5)0.5973 (6)0.2077 (4)0.0482 (13)
H190.62110.62680.22580.058*
C200.5886 (5)0.4942 (6)0.1778 (5)0.0573 (16)
H200.67020.45020.17670.069*
C210.4943 (5)0.4526 (5)0.1478 (4)0.0491 (14)
C220.3707 (5)0.5232 (4)0.1494 (4)0.0368 (11)
C230.2739 (6)0.4871 (5)0.1186 (4)0.0484 (13)
H230.19310.53330.11950.058*
C240.3013 (7)0.3822 (5)0.0872 (5)0.0593 (17)
H240.23840.35840.06570.071*
C250.4215 (8)0.3111 (5)0.0871 (5)0.069 (2)
H250.43720.23940.06730.083*
C260.5157 (7)0.3447 (5)0.1153 (5)0.0627 (18)
H260.59550.29680.11350.075*
C270.8604 (10)0.2512 (15)0.4852 (19)0.063 (5)0.50
H27A0.89670.32110.43650.075*0.50
H27B0.86140.25330.55530.075*0.50
C280.9396 (16)0.3811 (15)0.1973 (14)0.084 (5)0.50
H28A0.93680.35950.27220.127*0.50
H28B1.02060.34690.17260.127*0.50
H28C0.87930.34590.18000.127*0.50
C27'0.8070 (16)0.268 (3)0.3937 (11)0.063 (5)0.25
H27C0.79260.35600.34580.075*0.25
H27D0.86460.21780.35720.075*0.25
Cl10.9543 (4)0.1122 (4)0.4801 (3)0.0832 (11)0.50
Cl20.7078 (5)0.2804 (5)0.4571 (4)0.1066 (15)0.50
Cl1'0.6702 (5)0.2176 (5)0.4186 (4)0.0469 (13)0.25
Cl2'0.8778 (6)0.2622 (8)0.4995 (6)0.0486 (17)0.25
Cu10.17336 (5)0.74743 (5)0.18837 (5)0.0344 (2)
F10.885 (2)0.500 (2)0.1974 (16)0.100 (7)0.50
F21.0100 (8)0.5000 (9)0.0527 (6)0.092 (3)0.50
F31.0390 (6)0.3304 (6)0.2065 (5)0.0524 (15)0.50
F40.8734 (6)0.3674 (6)0.1137 (6)0.0619 (19)0.50
F50.5381 (10)1.0164 (9)1.0826 (7)0.099 (3)0.50
F60.4451 (7)0.9003 (7)1.0327 (6)0.067 (2)0.50
F70.6029 (6)0.9793 (7)0.9324 (6)0.069 (2)0.50
F80.4267 (7)1.1114 (7)0.9391 (6)0.079 (2)0.50
N10.0099 (3)1.3038 (3)0.7288 (3)0.0327 (8)
N20.0500 (4)1.3506 (4)0.6289 (3)0.0377 (9)
N30.0629 (3)1.1840 (3)0.9361 (3)0.0266 (8)
N40.3424 (3)0.6261 (3)0.1831 (3)0.0302 (8)
N50.2788 (3)0.8281 (3)0.2460 (3)0.0307 (8)
N60.2734 (4)0.9278 (4)0.2842 (3)0.0356 (9)
O10.1875 (3)1.2811 (3)0.7509 (2)0.0333 (7)
O20.4683 (3)0.8191 (3)0.2815 (3)0.0380 (8)
O30.915 (3)0.507 (2)0.1515 (17)0.097 (8)0.50
H3A0.88650.52650.09440.146*0.50
S10.29281 (12)1.37416 (14)0.56289 (10)0.0454 (3)
S20.44522 (12)1.01202 (13)0.35022 (11)0.0442 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.038 (5)0.040 (5)0.041 (5)0.007 (4)0.001 (4)0.013 (4)
B20.025 (4)0.035 (4)0.040 (4)0.002 (3)0.001 (3)0.019 (3)
C10.032 (2)0.024 (2)0.034 (2)0.0005 (17)0.0018 (19)0.0171 (19)
C20.031 (2)0.032 (2)0.043 (3)0.0036 (19)0.000 (2)0.018 (2)
C30.038 (3)0.042 (3)0.049 (3)0.003 (2)0.007 (2)0.020 (2)
C40.050 (3)0.041 (3)0.036 (3)0.003 (2)0.002 (2)0.012 (2)
C50.044 (3)0.037 (3)0.035 (3)0.003 (2)0.008 (2)0.013 (2)
C60.037 (3)0.028 (2)0.036 (2)0.0046 (19)0.006 (2)0.017 (2)
C70.033 (2)0.037 (2)0.038 (3)0.002 (2)0.012 (2)0.015 (2)
C80.026 (2)0.035 (2)0.043 (3)0.0017 (19)0.009 (2)0.019 (2)
C90.030 (2)0.029 (2)0.032 (2)0.0014 (18)0.0034 (18)0.0163 (19)
C100.025 (2)0.028 (2)0.036 (2)0.0023 (17)0.0016 (18)0.0157 (19)
C110.036 (3)0.041 (3)0.032 (3)0.007 (2)0.007 (2)0.011 (2)
C120.042 (3)0.061 (3)0.037 (3)0.014 (3)0.003 (2)0.012 (3)
C130.038 (3)0.064 (3)0.037 (3)0.007 (3)0.009 (2)0.019 (3)
C140.045 (3)0.058 (3)0.041 (3)0.016 (3)0.002 (2)0.018 (3)
C150.043 (3)0.062 (3)0.047 (3)0.013 (3)0.007 (2)0.026 (3)
C160.035 (3)0.044 (3)0.030 (2)0.013 (2)0.005 (2)0.010 (2)
C170.030 (2)0.043 (3)0.027 (2)0.010 (2)0.0080 (18)0.008 (2)
C180.028 (2)0.041 (3)0.027 (2)0.002 (2)0.0012 (18)0.009 (2)
C190.025 (2)0.067 (4)0.045 (3)0.003 (2)0.007 (2)0.016 (3)
C200.038 (3)0.063 (4)0.050 (3)0.020 (3)0.006 (3)0.013 (3)
C210.052 (3)0.040 (3)0.036 (3)0.010 (2)0.006 (2)0.007 (2)
C220.043 (3)0.028 (2)0.031 (2)0.001 (2)0.004 (2)0.0061 (19)
C230.058 (4)0.040 (3)0.051 (3)0.010 (3)0.008 (3)0.024 (3)
C240.087 (5)0.041 (3)0.055 (4)0.022 (3)0.020 (3)0.026 (3)
C250.117 (6)0.029 (3)0.050 (4)0.001 (3)0.013 (4)0.018 (3)
C260.079 (5)0.038 (3)0.045 (3)0.021 (3)0.007 (3)0.010 (3)
C270.060 (6)0.079 (6)0.059 (6)0.030 (4)0.010 (4)0.023 (4)
C280.072 (11)0.068 (10)0.087 (13)0.003 (9)0.010 (10)0.009 (10)
C27'0.060 (6)0.079 (6)0.059 (6)0.030 (4)0.010 (4)0.023 (4)
Cl10.083 (2)0.129 (3)0.0497 (17)0.055 (2)0.0073 (16)0.0284 (18)
Cl20.104 (3)0.109 (3)0.078 (2)0.046 (2)0.022 (2)0.023 (2)
Cl1'0.044 (3)0.057 (3)0.039 (3)0.033 (2)0.008 (2)0.000 (2)
Cl2'0.040 (3)0.089 (5)0.031 (3)0.033 (3)0.003 (2)0.026 (3)
Cu10.0253 (3)0.0394 (4)0.0416 (4)0.0007 (2)0.0082 (2)0.0188 (3)
F10.094 (8)0.079 (9)0.157 (19)0.019 (6)0.013 (11)0.084 (13)
F20.065 (5)0.110 (7)0.068 (5)0.022 (5)0.009 (4)0.011 (5)
F30.049 (4)0.065 (4)0.046 (4)0.019 (3)0.011 (3)0.016 (3)
F40.046 (4)0.056 (4)0.099 (5)0.010 (3)0.024 (4)0.051 (4)
F50.154 (9)0.103 (6)0.072 (6)0.061 (7)0.022 (6)0.039 (5)
F60.080 (5)0.067 (4)0.056 (4)0.046 (4)0.006 (4)0.003 (4)
F70.034 (3)0.077 (5)0.060 (4)0.013 (3)0.005 (3)0.002 (4)
F80.052 (4)0.063 (4)0.077 (5)0.017 (4)0.014 (4)0.003 (4)
N10.030 (2)0.033 (2)0.034 (2)0.0022 (16)0.0043 (16)0.0124 (17)
N20.036 (2)0.043 (2)0.032 (2)0.0080 (18)0.0017 (17)0.0103 (18)
N30.0268 (19)0.0236 (17)0.032 (2)0.0001 (14)0.0053 (15)0.0142 (15)
N40.0259 (19)0.0298 (19)0.0292 (19)0.0004 (15)0.0021 (15)0.0069 (16)
N50.028 (2)0.0300 (19)0.035 (2)0.0012 (16)0.0079 (16)0.0136 (16)
N60.036 (2)0.040 (2)0.035 (2)0.0073 (18)0.0079 (17)0.0162 (18)
O10.0270 (16)0.0407 (18)0.0332 (17)0.0071 (14)0.0017 (13)0.0141 (14)
O20.0293 (17)0.0470 (19)0.0384 (19)0.0081 (15)0.0076 (14)0.0133 (15)
O30.15 (2)0.036 (7)0.110 (16)0.003 (10)0.046 (14)0.028 (9)
S10.0382 (7)0.0649 (9)0.0371 (7)0.0176 (6)0.0002 (5)0.0189 (6)
S20.0400 (7)0.0553 (8)0.0455 (7)0.0160 (6)0.0075 (6)0.0210 (6)
Geometric parameters (Å, º) top
B1—F41.378 (7)C18—N41.336 (6)
B1—F11.385 (8)C18—C191.400 (7)
B1—F31.389 (7)C19—C201.347 (8)
B1—F21.390 (7)C19—H190.9300
B1—H3A1.2309C20—C211.419 (9)
B2—F6i1.332 (6)C20—H200.9300
B2—F61.332 (6)C21—C221.424 (7)
B2—F51.352 (7)C21—C261.424 (8)
B2—F5i1.352 (7)C22—N41.375 (6)
B2—F8i1.385 (7)C22—C231.412 (8)
B2—F81.385 (7)C23—C241.378 (7)
B2—F7i1.396 (6)C23—H230.9300
B2—F71.396 (6)C24—C251.393 (10)
C1—N31.371 (6)C24—H240.9300
C1—C21.405 (6)C25—C261.351 (10)
C1—C61.435 (6)C25—H250.9300
C2—C31.365 (7)C26—H260.9300
C2—H20.9300C27—Cl11.708 (10)
C3—C41.408 (7)C27—Cl21.725 (9)
C3—H30.9300C27—H27A0.9700
C4—C51.366 (8)C27—H27B0.9700
C4—H40.9300C28—O31.33 (3)
C5—C61.416 (7)C28—H28A0.9600
C5—H50.9300C28—H28B0.9600
C6—C71.406 (7)C28—H28C0.9600
C7—C81.370 (7)C27'—Cl1'1.709 (10)
C7—H70.9300C27'—Cl2'1.718 (10)
C8—C91.397 (6)C27'—H27C0.9700
C8—H80.9300C27'—H27D0.9700
C9—N31.335 (6)Cl1—Cl1ii2.423 (10)
C9—C101.456 (6)Cu1—N52.048 (4)
C10—N11.285 (6)Cu1—N3iii2.049 (3)
C10—O11.361 (5)Cu1—N42.069 (4)
C11—N21.295 (6)Cu1—N1iii2.093 (4)
C11—O11.364 (5)F1—H3A1.3268
C11—S11.737 (5)F2—F2iv1.489 (18)
C12—C131.517 (7)F2—H3A1.4182
C12—S11.815 (5)F5—F6i1.528 (11)
C12—H12A0.9700F5—F8i1.553 (12)
C12—H12B0.9700F5—F7i1.603 (12)
C13—C141.531 (7)F6—F8i1.497 (10)
C13—H13A0.9700F6—F5i1.528 (11)
C13—H13B0.9700F6—F7i1.577 (11)
C14—C151.530 (7)F7—F6i1.577 (11)
C14—H14A0.9700F7—F5i1.603 (12)
C14—H14B0.9700F7—F8i1.715 (10)
C15—S21.830 (6)F8—F6i1.497 (10)
C15—H15A0.9700F8—F5i1.553 (12)
C15—H15B0.9700F8—F7i1.715 (10)
C16—N61.293 (6)N1—N21.404 (5)
C16—O21.368 (6)N1—Cu1iii2.093 (4)
C16—S21.735 (5)N3—Cu1iii2.049 (3)
C17—N51.282 (6)N5—N61.411 (5)
C17—O21.362 (5)O3—H3A0.8200
C17—C181.463 (6)
F4—B1—F1109.3 (12)O2—C17—C18123.0 (4)
F4—B1—F3109.6 (7)N4—C18—C19124.7 (4)
F1—B1—F3108.4 (13)N4—C18—C17111.5 (4)
F4—B1—F2110.3 (8)C19—C18—C17123.8 (5)
F1—B1—F2108.3 (11)C20—C19—C18118.5 (5)
F3—B1—F2110.8 (7)C20—C19—H19120.7
F4—B1—H3A86.5C18—C19—H19120.7
F1—B1—H3A60.6C19—C20—C21119.9 (5)
F3—B1—H3A163.4C19—C20—H20120.0
F2—B1—H3A65.2C21—C20—H20120.0
F6i—B2—F6180.000 (3)C20—C21—C22118.4 (5)
F6i—B2—F569.4 (5)C20—C21—C26124.0 (6)
F6—B2—F5110.6 (5)C22—C21—C26117.7 (6)
F6i—B2—F5i110.6 (5)N4—C22—C23118.5 (4)
F6—B2—F5i69.4 (5)N4—C22—C21120.9 (5)
F5—B2—F5i180.000 (5)C23—C22—C21120.6 (5)
F6i—B2—F8i113.1 (5)C24—C23—C22118.7 (6)
F6—B2—F8i66.9 (5)C24—C23—H23120.6
F5—B2—F8i69.1 (6)C22—C23—H23120.6
F5i—B2—F8i110.9 (6)C23—C24—C25121.2 (6)
F6i—B2—F866.9 (5)C23—C24—H24119.4
F6—B2—F8113.1 (5)C25—C24—H24119.4
F5—B2—F8110.9 (6)C26—C25—C24121.0 (5)
F5i—B2—F869.1 (6)C26—C25—H25119.5
F8i—B2—F8180.000 (3)C24—C25—H25119.5
F6i—B2—F7i109.4 (5)C25—C26—C21120.8 (6)
F6—B2—F7i70.6 (5)C25—C26—H26119.6
F5—B2—F7i71.3 (5)C21—C26—H26119.6
F5i—B2—F7i108.7 (5)Cl1—C27—Cl2118.0 (8)
F8i—B2—F7i103.9 (4)Cl1—C27—H27A107.8
F8—B2—F7i76.1 (4)Cl2—C27—H27A107.8
F6i—B2—F770.6 (5)Cl1—C27—H27B107.8
F6—B2—F7109.4 (5)Cl2—C27—H27B107.8
F5—B2—F7108.7 (5)H27A—C27—H27B107.2
F5i—B2—F771.3 (5)O3—C28—H28A109.5
F8i—B2—F776.1 (4)O3—C28—H28B109.5
F8—B2—F7103.9 (4)H28A—C28—H28B109.5
F7i—B2—F7180.000 (2)O3—C28—H28C109.5
N3—C1—C2119.4 (4)H28A—C28—H28C109.5
N3—C1—C6121.2 (4)H28B—C28—H28C109.5
C2—C1—C6119.4 (4)Cl1'—C27'—Cl2'117.6 (9)
C3—C2—C1119.9 (5)Cl1'—C27'—H27C107.9
C3—C2—H2120.0Cl2'—C27'—H27C107.9
C1—C2—H2120.0Cl1'—C27'—H27D107.9
C2—C3—C4121.1 (5)Cl2'—C27'—H27D107.9
C2—C3—H3119.5H27C—C27'—H27D107.2
C4—C3—H3119.5C27—Cl1—Cl1ii162.2 (9)
C5—C4—C3120.7 (5)N5—Cu1—N3iii133.56 (14)
C5—C4—H4119.7N5—Cu1—N480.91 (14)
C3—C4—H4119.7N3iii—Cu1—N4120.30 (14)
C4—C5—C6119.9 (5)N5—Cu1—N1iii120.47 (15)
C4—C5—H5120.0N3iii—Cu1—N1iii81.60 (15)
C6—C5—H5120.0N4—Cu1—N1iii126.66 (14)
C7—C6—C5122.7 (4)B1—F1—H3A53.9
C7—C6—C1118.3 (4)B1—F2—F2iv119.2 (10)
C5—C6—C1118.9 (4)B1—F2—H3A52.0
C8—C7—C6120.0 (4)F2iv—F2—H3A101.5
C8—C7—H7120.0B2—F5—F6i54.7 (4)
C6—C7—H7120.0B2—F5—F8i56.4 (4)
C7—C8—C9117.9 (4)F6i—F5—F8i94.8 (6)
C7—C8—H8121.0B2—F5—F7i55.6 (4)
C9—C8—H8121.0F6i—F5—F7i90.7 (6)
N3—C9—C8125.3 (4)F8i—F5—F7i87.9 (6)
N3—C9—C10111.9 (4)B2—F6—F8i58.3 (4)
C8—C9—C10122.8 (4)B2—F6—F5i55.9 (4)
N1—C10—O1113.0 (4)F8i—F6—F5i96.3 (6)
N1—C10—C9125.4 (4)B2—F6—F7i56.6 (4)
O1—C10—C9121.6 (4)F8i—F6—F7i90.8 (5)
N2—C11—O1113.7 (4)F5i—F6—F7i91.9 (5)
N2—C11—S1131.7 (4)B2—F7—F6i52.8 (3)
O1—C11—S1114.5 (3)B2—F7—F5i53.0 (4)
C13—C12—S1113.5 (4)F6i—F7—F5i87.9 (5)
C13—C12—H12A108.9B2—F7—F8i51.6 (3)
S1—C12—H12A108.9F6i—F7—F8i87.0 (5)
C13—C12—H12B108.9F5i—F7—F8i85.5 (5)
S1—C12—H12B108.9B2—F8—F6i54.9 (4)
H12A—C12—H12B107.7B2—F8—F5i54.4 (4)
C12—C13—C14113.9 (4)F6i—F8—F5i92.6 (6)
C12—C13—H13A108.8B2—F8—F7i52.2 (3)
C14—C13—H13A108.8F6i—F8—F7i87.5 (5)
C12—C13—H13B108.8F5i—F8—F7i86.0 (5)
C14—C13—H13B108.8C10—N1—N2106.9 (4)
H13A—C13—H13B107.7C10—N1—Cu1iii107.1 (3)
C15—C14—C13110.1 (4)N2—N1—Cu1iii145.5 (3)
C15—C14—H14A109.6C11—N2—N1104.9 (4)
C13—C14—H14A109.6C9—N3—C1117.3 (4)
C15—C14—H14B109.6C9—N3—Cu1iii113.8 (3)
C13—C14—H14B109.6C1—N3—Cu1iii128.7 (3)
H14A—C14—H14B108.2C18—N4—C22117.5 (4)
C14—C15—S2108.6 (4)C18—N4—Cu1113.8 (3)
C14—C15—H15A110.0C22—N4—Cu1128.6 (3)
S2—C15—H15A110.0C17—N5—N6107.0 (3)
C14—C15—H15B110.0C17—N5—Cu1109.9 (3)
S2—C15—H15B110.0N6—N5—Cu1143.0 (3)
H15A—C15—H15B108.3C16—N6—N5104.3 (4)
N6—C16—O2114.3 (4)C10—O1—C11101.5 (3)
N6—C16—S2128.4 (4)C17—O2—C16101.1 (3)
O2—C16—S2117.4 (3)C28—O3—H3A109.7
N5—C17—O2113.2 (4)C11—S1—C1298.8 (2)
N5—C17—C18123.7 (4)C16—S2—C1597.2 (2)
N3—C1—C2—C3179.0 (4)F6i—B2—F7—F5i120.9 (5)
C6—C1—C2—C30.6 (6)F6—B2—F7—F5i59.1 (5)
C1—C2—C3—C40.4 (7)F5—B2—F7—F5i180.000 (4)
C2—C3—C4—C50.9 (7)F8i—B2—F7—F5i118.1 (6)
C3—C4—C5—C60.4 (7)F8—B2—F7—F5i61.9 (6)
C4—C5—C6—C7178.8 (4)F7i—B2—F7—F5i33 (100)
C4—C5—C6—C10.6 (6)F6i—B2—F7—F8i121.1 (5)
N3—C1—C6—C70.0 (6)F6—B2—F7—F8i58.9 (5)
C2—C1—C6—C7178.3 (4)F5—B2—F7—F8i61.9 (6)
N3—C1—C6—C5179.4 (4)F5i—B2—F7—F8i118.1 (6)
C2—C1—C6—C51.1 (6)F8—B2—F7—F8i180.000 (4)
C5—C6—C7—C8179.7 (4)F7i—B2—F7—F8i85 (100)
C1—C6—C7—C80.3 (6)F6—B2—F8—F6i180.000 (2)
C6—C7—C8—C90.3 (6)F5—B2—F8—F6i55.1 (6)
C7—C8—C9—N30.2 (7)F5i—B2—F8—F6i124.9 (6)
C7—C8—C9—C10180.0 (4)F8i—B2—F8—F6i120 (100)
N3—C9—C10—N16.2 (6)F7i—B2—F8—F6i118.5 (6)
C8—C9—C10—N1173.6 (4)F7—B2—F8—F6i61.5 (6)
N3—C9—C10—O1171.6 (4)F6i—B2—F8—F5i124.9 (6)
C8—C9—C10—O18.6 (6)F6—B2—F8—F5i55.1 (6)
S1—C12—C13—C1461.6 (5)F5—B2—F8—F5i180.000 (5)
C12—C13—C14—C15178.1 (4)F8i—B2—F8—F5i5 (100)
C13—C14—C15—S2177.0 (4)F7i—B2—F8—F5i116.5 (6)
N5—C17—C18—N42.0 (6)F7—B2—F8—F5i63.5 (6)
O2—C17—C18—N4177.8 (4)F6i—B2—F8—F7i118.5 (6)
N5—C17—C18—C19178.0 (5)F6—B2—F8—F7i61.5 (6)
O2—C17—C18—C192.2 (7)F5—B2—F8—F7i63.5 (6)
N4—C18—C19—C202.3 (8)F5i—B2—F8—F7i116.5 (6)
C17—C18—C19—C20177.7 (5)F8i—B2—F8—F7i122 (100)
C18—C19—C20—C211.6 (8)F7—B2—F8—F7i180.000 (4)
C19—C20—C21—C220.7 (8)O1—C10—N1—N20.1 (5)
C19—C20—C21—C26179.9 (5)C9—C10—N1—N2178.2 (4)
C20—C21—C22—N42.5 (7)O1—C10—N1—Cu1iii173.8 (3)
C26—C21—C22—N4178.0 (4)C9—C10—N1—Cu1iii4.2 (5)
C20—C21—C22—C23178.9 (5)O1—C11—N2—N10.7 (5)
C26—C21—C22—C230.6 (7)S1—C11—N2—N1178.5 (4)
N4—C22—C23—C24178.5 (5)C10—N1—N2—C110.3 (5)
C21—C22—C23—C240.1 (8)Cu1iii—N1—N2—C11170.0 (4)
C22—C23—C24—C251.0 (8)C8—C9—N3—C10.1 (6)
C23—C24—C25—C261.7 (9)C10—C9—N3—C1179.7 (3)
C24—C25—C26—C211.1 (9)C8—C9—N3—Cu1iii175.3 (3)
C20—C21—C26—C25179.5 (6)C10—C9—N3—Cu1iii4.5 (4)
C22—C21—C26—C250.0 (8)C2—C1—N3—C9178.5 (4)
Cl2—C27—Cl1—Cl1ii68 (3)C6—C1—N3—C90.2 (5)
F4—B1—F2—F2iv5.6 (15)C2—C1—N3—Cu1iii7.1 (5)
F1—B1—F2—F2iv125.3 (16)C6—C1—N3—Cu1iii174.6 (3)
F3—B1—F2—F2iv115.9 (11)C19—C18—N4—C220.5 (7)
F6—B2—F5—F6i180.000 (4)C17—C18—N4—C22179.6 (4)
F5i—B2—F5—F6i139 (100)C19—C18—N4—Cu1175.9 (4)
F8i—B2—F5—F6i126.3 (6)C17—C18—N4—Cu14.0 (5)
F8—B2—F5—F6i53.7 (6)C23—C22—N4—C18179.5 (4)
F7i—B2—F5—F6i120.1 (5)C21—C22—N4—C182.0 (6)
F7—B2—F5—F6i59.9 (6)C23—C22—N4—Cu13.7 (6)
F6i—B2—F5—F8i126.3 (6)C21—C22—N4—Cu1177.7 (3)
F6—B2—F5—F8i53.7 (6)N5—Cu1—N4—C183.8 (3)
F5i—B2—F5—F8i12 (100)N3iii—Cu1—N4—C18131.8 (3)
F8—B2—F5—F8i180.000 (7)N1iii—Cu1—N4—C18125.2 (3)
F7i—B2—F5—F8i113.5 (5)N5—Cu1—N4—C22179.7 (4)
F7—B2—F5—F8i66.5 (5)N3iii—Cu1—N4—C2244.1 (4)
F6i—B2—F5—F7i120.1 (5)N1iii—Cu1—N4—C2258.9 (4)
F6—B2—F5—F7i59.9 (5)O2—C17—N5—N60.3 (5)
F5i—B2—F5—F7i101 (100)C18—C17—N5—N6179.9 (4)
F8i—B2—F5—F7i113.5 (5)O2—C17—N5—Cu1179.0 (3)
F8—B2—F5—F7i66.5 (5)C18—C17—N5—Cu11.2 (5)
F7—B2—F5—F7i180.000 (3)N3iii—Cu1—N5—C17121.0 (3)
F6i—B2—F6—F8i97 (100)N4—Cu1—N5—C172.6 (3)
F5—B2—F6—F8i54.9 (7)N1iii—Cu1—N5—C17130.0 (3)
F5i—B2—F6—F8i125.1 (7)N3iii—Cu1—N5—N656.9 (5)
F8—B2—F6—F8i180.000 (2)N4—Cu1—N5—N6179.5 (5)
F7i—B2—F6—F8i115.3 (5)N1iii—Cu1—N5—N652.1 (5)
F7—B2—F6—F8i64.7 (5)O2—C16—N6—N50.5 (5)
F6i—B2—F6—F5i28 (100)S2—C16—N6—N5179.3 (4)
F5—B2—F6—F5i180.000 (4)C17—N5—N6—C160.1 (5)
F8i—B2—F6—F5i125.1 (7)Cu1—N5—N6—C16177.8 (4)
F8—B2—F6—F5i54.9 (7)N1—C10—O1—C110.5 (5)
F7i—B2—F6—F5i119.7 (6)C9—C10—O1—C11178.6 (4)
F7—B2—F6—F5i60.3 (6)N2—C11—O1—C100.8 (5)
F6i—B2—F6—F7i148 (100)S1—C11—O1—C10178.5 (3)
F5—B2—F6—F7i60.3 (6)N5—C17—O2—C160.5 (5)
F5i—B2—F6—F7i119.7 (6)C18—C17—O2—C16179.7 (4)
F8i—B2—F6—F7i115.3 (5)N6—C16—O2—C170.6 (5)
F8—B2—F6—F7i64.7 (5)S2—C16—O2—C17179.2 (3)
F7—B2—F6—F7i180.000 (2)N2—C11—S1—C126.2 (5)
F6—B2—F7—F6i180.000 (2)O1—C11—S1—C12174.7 (4)
F5—B2—F7—F6i59.1 (5)C13—C12—S1—C1176.2 (4)
F5i—B2—F7—F6i120.9 (5)N6—C16—S2—C151.2 (5)
F8i—B2—F7—F6i121.1 (5)O2—C16—S2—C15178.5 (4)
F8—B2—F7—F6i58.9 (5)C14—C15—S2—C16176.1 (4)
F7i—B2—F7—F6i154 (100)
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y, z+1; (iii) x, y+2, z+1; (iv) x+2, y+1, z.
(III) Bis(µ-1,4-bis{[5-(quinolin-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}butane)dicopper(I) bis(perchlorate)–dichloromethane–methanol (1/2/1) top
Crystal data top
[Cu2(C26H20N6O2S2)2](ClO4)2·2CH2Cl2·CH4OZ = 1
Mr = 1553.07F(000) = 790
Triclinic, P1Dx = 1.618 Mg m3
a = 11.2499 (11) ÅMo Kα radiation, λ = 0.7107 Å
b = 11.5798 (11) ÅCell parameters from 1468 reflections
c = 13.6976 (15) Åθ = 3.6–21.5°
α = 67.635 (10)°µ = 1.12 mm1
β = 81.106 (9)°T = 100 K
γ = 75.524 (8)°Plate, yellow
V = 1594.3 (3) Å30.16 × 0.10 × 0.02 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Eos detector
6039 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3134 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.068
Detector resolution: 16.0793 pixels mm-1θmax = 25.7°, θmin = 2.9°
ω scansh = 1313
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1314
Tmin = 0.949, Tmax = 1.000l = 1516
11239 measured reflections
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)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.251H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1066P)2]
where P = (Fo2 + 2Fc2)/3
6039 reflections(Δ/σ)max < 0.001
488 parametersΔρmax = 1.08 e Å3
17 restraintsΔρmin = 0.70 e Å3
Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/UeqOcc. (<1)
C10.6280 (7)0.9767 (7)0.3469 (6)0.046 (2)
C20.7198 (9)1.0121 (7)0.3798 (6)0.055 (2)
H20.80050.96620.37970.067*
C30.6914 (10)1.1146 (8)0.4124 (7)0.071 (3)
H30.75251.13580.43690.085*
C40.5705 (13)1.1881 (9)0.4093 (9)0.085 (4)
H40.55341.26080.42700.101*
C50.4812 (12)1.1535 (9)0.3811 (8)0.085 (4)
H50.40151.20120.38290.102*
C60.5013 (9)1.0467 (8)0.3481 (6)0.060 (3)
C70.4109 (9)1.0082 (9)0.3152 (8)0.070 (3)
H70.32981.05320.31420.084*
C80.4412 (7)0.9067 (8)0.2853 (6)0.056 (2)
H80.38150.87930.26480.067*
C90.5670 (6)0.8410 (7)0.2856 (6)0.0399 (18)
C100.6110 (6)0.7348 (7)0.2498 (6)0.0390 (18)
C110.6185 (7)0.5859 (7)0.1938 (6)0.0434 (19)
C120.7036 (7)0.3786 (8)0.1423 (7)0.053 (2)
H12A0.76460.42170.09360.063*
H12B0.73560.33790.21190.063*
C130.6778 (7)0.2789 (7)0.1062 (7)0.050 (2)
H13A0.63950.32100.03930.060*
H13B0.62080.23250.15770.060*
C140.7975 (7)0.1837 (8)0.0929 (6)0.048 (2)
H14A0.85210.23000.03830.057*
H14B0.83850.14660.15860.057*
C151.2239 (7)0.9225 (7)0.0640 (6)0.048 (2)
H15A1.14580.98100.06160.058*
H15B1.27730.96960.11930.058*
C161.1638 (7)0.8341 (7)0.1450 (6)0.0390 (18)
C171.0725 (6)0.7642 (6)0.2957 (6)0.0378 (18)
C181.0496 (6)0.7059 (6)0.4091 (6)0.0356 (17)
C191.1391 (6)0.6756 (6)0.4811 (6)0.0356 (17)
H191.21700.69310.45720.043*
C201.1096 (6)0.6205 (6)0.5860 (6)0.0385 (18)
H201.16770.60000.63480.046*
C210.9922 (7)0.5946 (6)0.6210 (6)0.0377 (18)
C220.9558 (7)0.5375 (7)0.7285 (6)0.045 (2)
H221.01090.51610.77980.054*
C230.8416 (7)0.5134 (7)0.7579 (6)0.048 (2)
H230.81920.47580.82940.058*
C240.7554 (7)0.5444 (7)0.6820 (7)0.050 (2)
H240.67760.52600.70360.060*
C250.7871 (6)0.6020 (7)0.5758 (7)0.0413 (19)
H250.72980.62430.52610.050*
C260.9061 (6)0.6273 (6)0.5424 (6)0.0372 (18)
C270.1362 (12)0.2382 (16)0.039 (3)0.145 (6)0.630 (6)
H27A0.11960.21340.01710.174*0.630 (6)
H27B0.10520.18080.10470.174*0.630 (6)
C280.066 (3)0.116 (3)0.287 (3)0.123 (13)0.50
H28A0.02000.15590.28680.185*0.50
H28B0.09640.12020.21640.185*0.50
H28C0.11060.15870.31140.185*0.50
Cl10.0450 (4)0.0756 (7)0.3597 (5)0.0512 (13)0.50
Cl20.50000.50000.50000.0448 (7)
Cl30.2924 (6)0.2066 (7)0.0425 (5)0.154 (3)0.630 (6)
Cl40.0483 (5)0.3867 (6)0.0207 (4)0.114 (2)0.630 (6)
C27'0.186 (2)0.234 (4)0.1104 (15)0.145 (6)0.370 (6)
H27C0.12930.29150.14120.174*0.370 (6)
H27D0.19550.14850.16280.174*0.370 (6)
Cl3'0.3244 (12)0.2776 (12)0.0791 (9)0.161 (4)0.370 (6)
Cl4'0.1245 (11)0.2386 (14)0.0009 (10)0.136 (4)0.370 (6)
Cu10.82680 (7)0.75212 (8)0.31192 (7)0.0409 (3)
N10.7250 (5)0.6744 (5)0.2502 (5)0.0370 (15)
N20.7308 (5)0.5751 (6)0.2122 (5)0.0434 (16)
N30.6580 (5)0.8743 (5)0.3147 (4)0.0373 (15)
N40.9354 (5)0.6829 (5)0.4375 (5)0.0320 (14)
N50.9904 (5)0.8031 (5)0.2275 (5)0.0382 (15)
N61.0508 (5)0.8484 (6)0.1277 (5)0.0421 (15)
O20.5374 (4)0.6848 (5)0.2138 (4)0.0453 (14)
O31.1857 (4)0.7785 (4)0.2503 (4)0.0393 (12)
O40.1237 (10)0.1271 (10)0.3936 (11)0.067 (4)0.50
O50.0137 (12)0.0094 (13)0.4502 (11)0.078 (4)0.50
O60.0466 (10)0.1727 (10)0.2964 (9)0.054 (3)0.50
O70.1137 (19)0.003 (2)0.2983 (19)0.071 (6)0.50
O80.5976 (11)0.4737 (16)0.4306 (12)0.100 (6)0.50
O90.547 (2)0.502 (3)0.5845 (14)0.158 (9)0.50
O100.4399 (18)0.4042 (16)0.5362 (12)0.103 (6)0.50
O110.4313 (16)0.6181 (14)0.4412 (15)0.122 (7)0.50
O1M0.080 (3)0.006 (3)0.3509 (19)0.115 (10)0.50
H1M0.08770.05120.31520.172*0.50
S10.56145 (18)0.4933 (2)0.14653 (18)0.0543 (6)
S21.29163 (18)0.8690 (2)0.06107 (17)0.0533 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.060 (5)0.027 (4)0.035 (5)0.003 (4)0.003 (4)0.002 (3)
C20.086 (7)0.033 (4)0.048 (5)0.009 (4)0.006 (5)0.019 (4)
C30.118 (9)0.042 (5)0.054 (6)0.022 (6)0.010 (5)0.022 (4)
C40.146 (12)0.024 (5)0.064 (7)0.005 (6)0.006 (7)0.014 (4)
C50.121 (10)0.045 (6)0.053 (7)0.022 (6)0.017 (6)0.010 (5)
C60.077 (7)0.038 (5)0.037 (5)0.022 (5)0.007 (4)0.007 (4)
C70.053 (6)0.059 (6)0.068 (7)0.023 (5)0.010 (5)0.010 (5)
C80.027 (4)0.064 (6)0.052 (6)0.015 (4)0.009 (4)0.008 (4)
C90.038 (4)0.039 (4)0.034 (4)0.005 (4)0.004 (3)0.012 (3)
C100.033 (4)0.046 (4)0.035 (4)0.008 (4)0.011 (3)0.009 (3)
C110.038 (4)0.046 (5)0.046 (5)0.009 (4)0.008 (4)0.014 (4)
C120.048 (5)0.063 (5)0.055 (6)0.012 (4)0.009 (4)0.028 (4)
C130.045 (5)0.055 (5)0.049 (5)0.016 (4)0.007 (4)0.010 (4)
C140.040 (4)0.062 (5)0.039 (5)0.010 (4)0.009 (4)0.014 (4)
C150.056 (5)0.049 (5)0.038 (5)0.011 (4)0.010 (4)0.012 (4)
C160.043 (4)0.040 (4)0.036 (5)0.000 (4)0.010 (4)0.018 (3)
C170.036 (4)0.031 (4)0.050 (5)0.001 (3)0.006 (4)0.020 (3)
C180.032 (4)0.030 (4)0.047 (5)0.003 (3)0.010 (3)0.020 (3)
C190.025 (4)0.035 (4)0.047 (5)0.000 (3)0.005 (3)0.018 (3)
C200.034 (4)0.041 (4)0.044 (5)0.001 (4)0.011 (3)0.022 (4)
C210.047 (5)0.024 (4)0.042 (5)0.001 (3)0.006 (4)0.016 (3)
C220.043 (5)0.039 (4)0.051 (5)0.005 (4)0.012 (4)0.019 (4)
C230.048 (5)0.043 (5)0.045 (5)0.008 (4)0.007 (4)0.017 (4)
C240.039 (5)0.047 (5)0.064 (6)0.001 (4)0.006 (4)0.027 (4)
C250.034 (4)0.034 (4)0.054 (5)0.007 (3)0.009 (4)0.020 (4)
C260.033 (4)0.026 (4)0.052 (5)0.002 (3)0.005 (4)0.017 (3)
C270.134 (8)0.204 (9)0.109 (12)0.063 (7)0.017 (7)0.049 (8)
C280.07 (2)0.13 (3)0.14 (3)0.01 (2)0.00 (2)0.03 (3)
Cl10.048 (3)0.047 (3)0.073 (4)0.011 (3)0.006 (3)0.036 (3)
Cl20.0365 (15)0.0434 (16)0.060 (2)0.0084 (14)0.0004 (14)0.0260 (14)
Cl30.175 (5)0.158 (6)0.110 (4)0.106 (4)0.069 (4)0.039 (4)
Cl40.131 (5)0.169 (6)0.070 (3)0.083 (4)0.026 (3)0.052 (3)
C27'0.134 (8)0.204 (9)0.109 (12)0.063 (7)0.017 (7)0.049 (8)
Cl3'0.186 (6)0.158 (7)0.117 (6)0.096 (5)0.058 (5)0.031 (5)
Cl4'0.129 (7)0.197 (9)0.104 (10)0.065 (6)0.018 (6)0.056 (7)
Cu10.0297 (5)0.0432 (6)0.0517 (7)0.0010 (4)0.0122 (4)0.0208 (5)
N10.030 (3)0.034 (3)0.048 (4)0.001 (3)0.014 (3)0.017 (3)
N20.037 (4)0.049 (4)0.051 (4)0.001 (3)0.010 (3)0.028 (3)
N30.039 (3)0.032 (3)0.035 (4)0.001 (3)0.005 (3)0.009 (3)
N40.027 (3)0.026 (3)0.043 (4)0.004 (3)0.007 (3)0.015 (3)
N50.039 (3)0.033 (3)0.040 (4)0.009 (3)0.006 (3)0.009 (3)
N60.039 (4)0.047 (4)0.041 (4)0.007 (3)0.003 (3)0.018 (3)
O20.030 (3)0.047 (3)0.060 (4)0.004 (2)0.020 (2)0.015 (3)
O30.032 (3)0.041 (3)0.045 (3)0.008 (2)0.005 (2)0.014 (2)
O40.053 (7)0.045 (6)0.114 (11)0.009 (6)0.034 (7)0.042 (7)
O50.065 (8)0.080 (9)0.083 (12)0.005 (7)0.022 (8)0.022 (9)
O60.054 (7)0.051 (7)0.056 (8)0.004 (6)0.026 (6)0.014 (6)
O70.081 (11)0.067 (13)0.092 (17)0.021 (9)0.008 (11)0.060 (14)
O80.038 (7)0.109 (12)0.092 (12)0.025 (8)0.017 (7)0.003 (9)
O90.26 (3)0.22 (2)0.078 (14)0.17 (2)0.007 (14)0.068 (14)
O100.145 (15)0.096 (11)0.076 (11)0.088 (12)0.046 (10)0.013 (9)
O110.087 (12)0.067 (10)0.125 (15)0.034 (9)0.033 (10)0.013 (10)
O1M0.21 (3)0.071 (16)0.08 (2)0.036 (17)0.017 (17)0.037 (15)
S10.0433 (12)0.0646 (14)0.0649 (15)0.0132 (11)0.0180 (10)0.0274 (11)
S20.0460 (12)0.0725 (15)0.0473 (14)0.0215 (11)0.0024 (10)0.0225 (11)
Geometric parameters (Å, º) top
C1—N31.367 (9)C23—H230.9300
C1—C21.391 (11)C24—C251.381 (11)
C1—C61.454 (11)C24—H240.9300
C2—C31.370 (11)C25—C261.412 (10)
C2—H20.9300C25—H250.9300
C3—C41.410 (14)C26—N41.357 (9)
C3—H30.9300C27—Cl41.703 (10)
C4—C51.325 (15)C27—Cl31.708 (10)
C4—H40.9300C27—H27A0.9700
C5—C61.428 (14)C27—H27B0.9700
C5—H50.9300C28—O1M1.33 (4)
C6—C71.398 (13)C28—H28A0.9600
C7—C81.338 (13)C28—H28B0.9600
C7—H70.9300C28—H28C0.9600
C8—C91.429 (9)Cl1—O41.399 (12)
C8—H80.9300Cl1—O71.421 (9)
C9—N31.340 (9)Cl1—O61.426 (12)
C9—C101.441 (10)Cl1—O51.444 (16)
C10—N11.297 (8)Cl1—H1M1.7303
C10—O21.359 (8)Cl2—O101.336 (13)
C11—N21.293 (8)Cl2—O10ii1.336 (13)
C11—O21.363 (9)Cl2—O91.352 (15)
C11—S11.727 (8)Cl2—O9ii1.352 (15)
C12—C131.520 (11)Cl2—O8ii1.390 (13)
C12—S11.814 (8)Cl2—O81.390 (13)
C12—H12A0.9700Cl2—O111.394 (12)
C12—H12B0.9700Cl2—O11ii1.394 (13)
C13—C141.548 (11)Cl4—Cl4iii2.453 (14)
C13—H13A0.9700C27'—Cl3'1.699 (10)
C13—H13B0.9700C27'—Cl4'1.724 (10)
C14—C15i1.509 (10)C27'—H27C0.9700
C14—H14A0.9700C27'—H27D0.9700
C14—H14B0.9700Cu1—N42.051 (5)
C15—C14i1.509 (10)Cu1—N12.057 (6)
C15—S21.806 (7)Cu1—N32.070 (5)
C15—H15A0.9700Cu1—N52.106 (6)
C15—H15B0.9700N1—N21.416 (8)
C16—N61.287 (8)N5—N61.398 (8)
C16—O31.371 (8)O5—O5iv1.55 (3)
C16—S21.726 (8)O7—H1M0.7036
C17—N51.291 (8)O8—O10ii1.59 (2)
C17—O31.348 (8)O8—O9ii1.61 (2)
C17—C181.449 (10)O8—O11ii1.70 (2)
C18—N41.345 (8)O9—O11ii1.51 (3)
C18—C191.406 (9)O9—O10ii1.61 (2)
C19—C201.358 (10)O9—O8ii1.61 (2)
C19—H190.9300O10—O11ii1.47 (2)
C20—C211.399 (9)O10—O8ii1.59 (2)
C20—H200.9300O10—O9ii1.61 (2)
C21—C221.408 (10)O11—O10ii1.47 (2)
C21—C261.439 (10)O11—O9ii1.51 (3)
C22—C231.350 (10)O11—O8ii1.70 (2)
C22—H220.9300O1M—H1M0.8200
C23—C241.416 (10)
N3—C1—C2119.2 (7)O1M—C28—H28C109.5
N3—C1—C6120.3 (8)H28A—C28—H28C109.5
C2—C1—C6120.5 (8)H28B—C28—H28C109.5
C3—C2—C1120.0 (9)O4—Cl1—O7109.9 (11)
C3—C2—H2120.0O4—Cl1—O6111.8 (7)
C1—C2—H2120.0O7—Cl1—O6108.1 (14)
C2—C3—C4120.8 (10)O4—Cl1—O5109.8 (9)
C2—C3—H3119.6O7—Cl1—O5107.8 (13)
C4—C3—H3119.6O6—Cl1—O5109.5 (7)
C5—C4—C3120.0 (10)O4—Cl1—H1M126.3
C5—C4—H4120.0O7—Cl1—H1M23.2
C3—C4—H4120.0O6—Cl1—H1M110.1
C4—C5—C6123.2 (11)O5—Cl1—H1M85.7
C4—C5—H5118.4O10—Cl2—O10ii180.000 (3)
C6—C5—H5118.4O10—Cl2—O9106.7 (10)
C7—C6—C5125.5 (10)O10ii—Cl2—O973.3 (10)
C7—C6—C1119.1 (8)O10—Cl2—O9ii73.3 (10)
C5—C6—C1115.4 (10)O10ii—Cl2—O9ii106.7 (10)
C8—C7—C6120.0 (8)O9—Cl2—O9ii180.000 (4)
C8—C7—H7120.0O10—Cl2—O8ii71.1 (10)
C6—C7—H7120.0O10ii—Cl2—O8ii108.9 (10)
C7—C8—C9118.8 (9)O9—Cl2—O8ii71.9 (12)
C7—C8—H8120.6O9ii—Cl2—O8ii108.1 (12)
C9—C8—H8120.6O10—Cl2—O8108.9 (10)
N3—C9—C8124.0 (7)O10ii—Cl2—O871.1 (10)
N3—C9—C10112.4 (6)O9—Cl2—O8108.1 (12)
C8—C9—C10123.5 (7)O9ii—Cl2—O871.9 (12)
N1—C10—O2112.3 (7)O8ii—Cl2—O8180.000 (3)
N1—C10—C9123.9 (6)O10—Cl2—O11115.1 (9)
O2—C10—C9123.8 (6)O10ii—Cl2—O1164.9 (9)
N2—C11—O2114.2 (7)O9—Cl2—O11113.3 (13)
N2—C11—S1128.3 (6)O9ii—Cl2—O1166.7 (13)
O2—C11—S1117.6 (5)O8ii—Cl2—O1175.4 (8)
C13—C12—S1108.8 (5)O8—Cl2—O11104.6 (8)
C13—C12—H12A109.9O10—Cl2—O11ii64.9 (9)
S1—C12—H12A109.9O10ii—Cl2—O11ii115.1 (9)
C13—C12—H12B109.9O9—Cl2—O11ii66.7 (13)
S1—C12—H12B109.9O9ii—Cl2—O11ii113.3 (13)
H12A—C12—H12B108.3O8ii—Cl2—O11ii104.6 (8)
C12—C13—C14111.3 (6)O8—Cl2—O11ii75.4 (8)
C12—C13—H13A109.4O11—Cl2—O11ii180.0 (16)
C14—C13—H13A109.4C27—Cl4—Cl4iii170.7 (9)
C12—C13—H13B109.4Cl3'—C27'—Cl4'111.7 (12)
C14—C13—H13B109.4Cl3'—C27'—H27C109.3
H13A—C13—H13B108.0Cl4'—C27'—H27C109.3
C15i—C14—C13113.5 (6)Cl3'—C27'—H27D109.3
C15i—C14—H14A108.9Cl4'—C27'—H27D109.3
C13—C14—H14A108.9H27C—C27'—H27D107.9
C15i—C14—H14B108.9N4—Cu1—N1134.8 (2)
C13—C14—H14B108.9N4—Cu1—N3120.6 (2)
H14A—C14—H14B107.7N1—Cu1—N381.0 (2)
C14i—C15—S2114.2 (5)N4—Cu1—N581.9 (2)
C14i—C15—H15A108.7N1—Cu1—N5118.6 (2)
S2—C15—H15A108.7N3—Cu1—N5126.6 (2)
C14i—C15—H15B108.7C10—N1—N2107.0 (5)
S2—C15—H15B108.7C10—N1—Cu1109.2 (5)
H15A—C15—H15B107.6N2—N1—Cu1143.7 (4)
N6—C16—O3113.0 (6)C11—N2—N1104.4 (6)
N6—C16—S2132.2 (6)C9—N3—C1117.7 (6)
O3—C16—S2114.7 (5)C9—N3—Cu1113.3 (5)
N5—C17—O3112.9 (7)C1—N3—Cu1128.9 (5)
N5—C17—C18124.8 (7)C18—N4—C26117.3 (6)
O3—C17—C18122.3 (6)C18—N4—Cu1112.8 (5)
N4—C18—C19124.0 (7)C26—N4—Cu1129.7 (4)
N4—C18—C17113.2 (6)C17—N5—N6106.6 (6)
C19—C18—C17122.8 (7)C17—N5—Cu1107.0 (5)
C20—C19—C18118.7 (7)N6—N5—Cu1145.8 (4)
C20—C19—H19120.6C16—N6—N5105.5 (6)
C18—C19—H19120.6C10—O2—C11102.1 (5)
C19—C20—C21120.2 (6)C17—O3—C16101.9 (5)
C19—C20—H20119.9Cl1—O5—O5iv107.5 (13)
C21—C20—H20119.9Cl1—O7—H1M103.9
C20—C21—C22123.1 (7)Cl2—O8—O10ii52.9 (8)
C20—C21—C26117.8 (7)Cl2—O8—O9ii53.0 (7)
C22—C21—C26119.2 (7)O10ii—O8—O9ii84.9 (11)
C23—C22—C21120.7 (7)Cl2—O8—O11ii52.4 (6)
C23—C22—H22119.7O10ii—O8—O11ii88.9 (11)
C21—C22—H22119.7O9ii—O8—O11ii87.6 (11)
C22—C23—C24121.2 (8)Cl2—O9—O11ii58.0 (9)
C22—C23—H23119.4Cl2—O9—O10ii52.9 (8)
C24—C23—H23119.4O11ii—O9—O10ii95.3 (13)
C25—C24—C23119.9 (7)Cl2—O9—O8ii55.2 (9)
C25—C24—H24120.1O11ii—O9—O8ii89.8 (12)
C23—C24—H24120.1O10ii—O9—O8ii87.2 (13)
C24—C25—C26120.3 (7)Cl2—O10—O11ii59.4 (8)
C24—C25—H25119.9Cl2—O10—O8ii56.0 (7)
C26—C25—H25119.9O11ii—O10—O8ii92.3 (11)
N4—C26—C25119.2 (6)Cl2—O10—O9ii53.8 (7)
N4—C26—C21122.1 (6)O11ii—O10—O9ii96.5 (14)
C25—C26—C21118.8 (7)O8ii—O10—O9ii88.2 (12)
Cl4—C27—Cl3122.0 (11)Cl2—O11—O10ii55.6 (8)
Cl4—C27—H27A106.8Cl2—O11—O9ii55.3 (9)
Cl3—C27—H27A106.8O10ii—O11—O9ii92.8 (13)
Cl4—C27—H27B106.8Cl2—O11—O8ii52.2 (6)
Cl3—C27—H27B106.8O10ii—O11—O8ii88.5 (12)
H27A—C27—H27B106.7O9ii—O11—O8ii87.2 (12)
O1M—C28—H28A109.5C28—O1M—H1M109.0
O1M—C28—H28B109.5C11—S1—C1297.6 (4)
H28A—C28—H28B109.5C16—S2—C1599.0 (4)
N3—C1—C2—C3180.0 (7)N3—Cu1—N5—N667.8 (9)
C6—C1—C2—C30.8 (12)O3—C16—N6—N51.7 (8)
C1—C2—C3—C42.4 (13)S2—C16—N6—N5179.6 (6)
C2—C3—C4—C54.4 (15)C17—N5—N6—C160.8 (7)
C3—C4—C5—C63.0 (17)Cu1—N5—N6—C16169.8 (6)
C4—C5—C6—C7178.4 (11)N1—C10—O2—C110.9 (8)
C4—C5—C6—C10.1 (14)C9—C10—O2—C11177.8 (7)
N3—C1—C6—C70.3 (11)N2—C11—O2—C101.3 (8)
C2—C1—C6—C7179.5 (8)S1—C11—O2—C10179.5 (5)
N3—C1—C6—C5178.8 (7)N5—C17—O3—C161.3 (7)
C2—C1—C6—C52.0 (11)C18—C17—O3—C16178.9 (6)
C5—C6—C7—C8179.6 (8)N6—C16—O3—C171.9 (8)
C1—C6—C7—C81.3 (13)S2—C16—O3—C17179.2 (5)
C6—C7—C8—C91.3 (13)O4—Cl1—O5—O5iv10.8 (15)
C7—C8—C9—N30.4 (12)O7—Cl1—O5—O5iv130.4 (16)
C7—C8—C9—C10176.7 (8)O6—Cl1—O5—O5iv112.2 (12)
N3—C9—C10—N12.9 (10)O10—Cl2—O8—O10ii180.000 (2)
C8—C9—C10—N1179.7 (7)O9—Cl2—O8—O10ii64.5 (12)
N3—C9—C10—O2178.5 (6)O9ii—Cl2—O8—O10ii115.5 (12)
C8—C9—C10—O21.1 (11)O8ii—Cl2—O8—O10ii159 (100)
S1—C12—C13—C14175.8 (5)O11—Cl2—O8—O10ii56.5 (11)
C12—C13—C14—C15i176.2 (6)O11ii—Cl2—O8—O10ii123.5 (11)
N5—C17—C18—N46.7 (10)O10—Cl2—O8—O9ii64.5 (12)
O3—C17—C18—N4170.6 (6)O10ii—Cl2—O8—O9ii115.5 (12)
N5—C17—C18—C19174.0 (7)O9—Cl2—O8—O9ii180.000 (2)
O3—C17—C18—C198.7 (10)O8ii—Cl2—O8—O9ii43 (100)
N4—C18—C19—C200.4 (10)O11—Cl2—O8—O9ii59.0 (13)
C17—C18—C19—C20179.7 (6)O11ii—Cl2—O8—O9ii121.0 (13)
C18—C19—C20—C210.1 (10)O10—Cl2—O8—O11ii56.5 (11)
C19—C20—C21—C22179.9 (6)O10ii—Cl2—O8—O11ii123.5 (11)
C19—C20—C21—C260.5 (10)O9—Cl2—O8—O11ii59.0 (13)
C20—C21—C22—C23179.4 (7)O9ii—Cl2—O8—O11ii121.0 (13)
C26—C21—C22—C230.0 (10)O8ii—Cl2—O8—O11ii78 (100)
C21—C22—C23—C240.2 (11)O11—Cl2—O8—O11ii180.000 (4)
C22—C23—C24—C251.0 (11)O10—Cl2—O9—O11ii52.4 (13)
C23—C24—C25—C261.6 (11)O10ii—Cl2—O9—O11ii127.6 (13)
C24—C25—C26—N4179.4 (6)O9ii—Cl2—O9—O11ii37 (100)
C24—C25—C26—C211.4 (10)O8ii—Cl2—O9—O11ii115.4 (11)
C20—C21—C26—N40.8 (10)O8—Cl2—O9—O11ii64.6 (11)
C22—C21—C26—N4179.8 (6)O11—Cl2—O9—O11ii180.000 (4)
C20—C21—C26—C25180.0 (6)O10—Cl2—O9—O10ii180.000 (3)
C22—C21—C26—C250.6 (9)O9ii—Cl2—O9—O10ii91 (100)
Cl3—C27—Cl4—Cl4iii28 (9)O8ii—Cl2—O9—O10ii117.0 (12)
O2—C10—N1—N20.2 (8)O8—Cl2—O9—O10ii63.0 (12)
C9—C10—N1—N2178.5 (7)O11—Cl2—O9—O10ii52.4 (13)
O2—C10—N1—Cu1177.5 (5)O11ii—Cl2—O9—O10ii127.6 (13)
C9—C10—N1—Cu11.2 (9)O10—Cl2—O9—O8ii63.0 (12)
N4—Cu1—N1—C10121.5 (5)O10ii—Cl2—O9—O8ii117.0 (12)
N3—Cu1—N1—C103.1 (5)O9ii—Cl2—O9—O8ii152 (100)
N5—Cu1—N1—C10130.0 (5)O8—Cl2—O9—O8ii180.000 (2)
N4—Cu1—N1—N254.1 (9)O11—Cl2—O9—O8ii64.6 (11)
N3—Cu1—N1—N2178.8 (8)O11ii—Cl2—O9—O8ii115.4 (11)
N5—Cu1—N1—N254.3 (8)O10ii—Cl2—O10—O11ii87 (100)
O2—C11—N2—N11.2 (8)O9—Cl2—O10—O11ii53.5 (15)
S1—C11—N2—N1179.7 (6)O9ii—Cl2—O10—O11ii126.5 (15)
C10—N1—N2—C110.6 (8)O8ii—Cl2—O10—O11ii117.0 (12)
Cu1—N1—N2—C11175.1 (6)O8—Cl2—O10—O11ii63.0 (12)
C8—C9—N3—C10.5 (11)O11—Cl2—O10—O11ii180.000 (2)
C10—C9—N3—C1177.9 (6)O10ii—Cl2—O10—O8ii156 (100)
C8—C9—N3—Cu1177.2 (6)O9—Cl2—O10—O8ii63.5 (14)
C10—C9—N3—Cu15.4 (8)O9ii—Cl2—O10—O8ii116.5 (14)
C2—C1—N3—C9178.7 (7)O8—Cl2—O10—O8ii180.000 (2)
C6—C1—N3—C90.5 (10)O11—Cl2—O10—O8ii63.0 (12)
C2—C1—N3—Cu12.6 (10)O11ii—Cl2—O10—O8ii117.0 (12)
C6—C1—N3—Cu1176.6 (5)O10ii—Cl2—O10—O9ii40 (100)
N4—Cu1—N3—C9132.5 (5)O9—Cl2—O10—O9ii180.000 (4)
N1—Cu1—N3—C94.9 (5)O8ii—Cl2—O10—O9ii116.5 (14)
N5—Cu1—N3—C9124.0 (5)O8—Cl2—O10—O9ii63.5 (14)
N4—Cu1—N3—C143.7 (7)O11—Cl2—O10—O9ii53.5 (15)
N1—Cu1—N3—C1178.9 (6)O11ii—Cl2—O10—O9ii126.5 (15)
N5—Cu1—N3—C159.8 (7)O10—Cl2—O11—O10ii180.000 (2)
C19—C18—N4—C260.1 (9)O9—Cl2—O11—O10ii56.9 (14)
C17—C18—N4—C26179.4 (6)O9ii—Cl2—O11—O10ii123.1 (14)
C19—C18—N4—Cu1175.7 (5)O8ii—Cl2—O11—O10ii119.4 (13)
C17—C18—N4—Cu15.0 (7)O8—Cl2—O11—O10ii60.6 (13)
C25—C26—N4—C18179.7 (6)O11ii—Cl2—O11—O10ii47 (100)
C21—C26—N4—C180.5 (9)O10—Cl2—O11—O9ii56.9 (14)
C25—C26—N4—Cu15.0 (9)O10ii—Cl2—O11—O9ii123.1 (14)
C21—C26—N4—Cu1174.2 (5)O9—Cl2—O11—O9ii180.000 (5)
N1—Cu1—N4—C18125.1 (5)O8ii—Cl2—O11—O9ii117.5 (13)
N3—Cu1—N4—C18125.5 (4)O8—Cl2—O11—O9ii62.5 (13)
N5—Cu1—N4—C182.4 (4)O11ii—Cl2—O11—O9ii76 (100)
N1—Cu1—N4—C2660.0 (7)O10—Cl2—O11—O8ii60.6 (13)
N3—Cu1—N4—C2649.4 (6)O10ii—Cl2—O11—O8ii119.4 (13)
N5—Cu1—N4—C26177.3 (6)O9—Cl2—O11—O8ii62.5 (13)
O3—C17—N5—N60.4 (8)O9ii—Cl2—O11—O8ii117.5 (13)
C18—C17—N5—N6177.9 (6)O8—Cl2—O11—O8ii180.000 (5)
O3—C17—N5—Cu1173.2 (4)O11ii—Cl2—O11—O8ii167 (100)
C18—C17—N5—Cu14.3 (8)N2—C11—S1—C123.7 (8)
N4—Cu1—N5—C170.9 (5)O2—C11—S1—C12177.2 (6)
N1—Cu1—N5—C17136.3 (5)C13—C12—S1—C11177.7 (6)
N3—Cu1—N5—C17123.2 (5)N6—C16—S2—C154.3 (8)
N4—Cu1—N5—N6169.9 (8)O3—C16—S2—C15174.4 (5)
N1—Cu1—N5—N632.7 (8)C14i—C15—S2—C1675.4 (6)
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y+1, z; (iv) x, y, z+1.
 

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