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In the title compound, [Cu(C6H5N2O4S3)(C10H8N2)2](C6H5N2O4S3)·2H2O, the CuII atom is coordinated by four N atoms from two bipyridine ligands and one O atom from the [5-(carboxy­methyl­sulfanyl)-1,3,4-thia­diazol-2-ylsulfanyl]acetate unit. The five-coordinate environment is intermediate between a trigonal bipyramid and a square pyramid. The complex cations and anions are connected with the water molecules via O—H...O hydrogen bonds to form layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032647/ob6456sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032647/ob6456Isup2.hkl
Contains datablock I

CCDC reference: 262264

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.052
  • wR factor = 0.156
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C32 PLAT731_ALERT_1_B Bond Calc 0.85(5), Rep 0.860(10) ...... 5.00 su-Rat O2W -H2W2 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.85(5), Rep 0.860(10) ...... 5.00 su-Rat O2W -H4# 1.555 1.555
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.605 0.856 Tmin' and Tmax expected: 0.700 0.852 RR' = 0.860 Please check that your absorption correction is appropriate. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.56 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S5 in Main Residue . ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O1W -H1W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.860(10) ...... 4.00 su-Rat O2W -H2W1 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 109(5), Rep 109(2) ...... 2.50 su-Rat H2W1 -O2W -H2W2 1.555 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O1W -H2# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O1W -H1# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.860(10) ...... 4.00 su-Rat O2W -H3# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.84(5), Rep 1.84(2) ...... 2.50 su-Rat H4# -O1W 1.555 1.555
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 20 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(2,2'-bipyridine-κN,N'){[5-(carboxymethylsulfanyl)-1,3,4-thiadiazol-2- ylsulfanyl]acetato-κO}copper(II) 5-(carboxymethylsulfanyl)-1,3,4-thiadiazol-2-ylsulfanylacetate dihydrate top
Crystal data top
[Cu(C6H5N2O4S3)(C10H8N2)2](C6H5N2O4S3)·2H2OZ = 2
Mr = 942.54F(000) = 966
Triclinic, P1Dx = 1.597 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.900 (2) ÅCell parameters from 16305 reflections
b = 12.197 (2) Åθ = 3.2–27.5°
c = 14.772 (3) ŵ = 0.94 mm1
α = 91.86 (1)°T = 295 K
β = 91.53 (2)°Block, blue
γ = 92.28 (1)°0.37 × 0.26 × 0.17 mm
V = 1960.6 (7) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
8693 independent reflections
Radiation source: fine-focus sealed tube6237 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scanθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1214
Tmin = 0.605, Tmax = 0.856k = 1515
18913 measured reflectionsl = 1919
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.091P)2 + 0.5195P]
where P = (Fo2 + 2Fc2)/3
8693 reflections(Δ/σ)max = 0.001
541 parametersΔρmax = 0.69 e Å3
14 restraintsΔρmin = 0.44 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.49685 (3)0.49718 (3)0.26028 (2)0.0375 (1)
S10.0565 (1)0.4230 (1)0.3333 (1)0.0556 (3)
S20.0963 (1)0.6143 (1)0.2847 (1)0.0542 (2)
S30.1645 (1)0.7719 (1)0.1407 (1)0.0638 (3)
S40.0929 (1)0.1312 (1)0.3123 (1)0.0742 (3)
S50.0698 (1)0.2121 (1)0.5035 (1)0.0615 (3)
S60.1311 (1)0.1629 (1)0.7018 (1)0.0638 (3)
O10.3231 (2)0.4618 (2)0.2928 (2)0.045 (1)
O20.3285 (3)0.3436 (2)0.1757 (2)0.059 (1)
O30.0513 (4)0.8840 (3)0.0594 (3)0.090 (1)
O40.0171 (5)0.8331 (4)0.0835 (3)0.114 (2)
O50.3140 (4)0.1269 (4)0.3158 (3)0.074 (1)0.735 (6)
O60.3619 (4)0.0468 (4)0.2879 (4)0.077 (2)0.735 (6)
O5'0.379 (1)0.062 (1)0.294 (1)0.074 (1)0.265 (6)
O6'0.358 (1)0.119 (1)0.313 (1)0.077 (2)0.265 (6)
O70.4011 (3)0.0214 (5)0.7084 (3)0.110 (2)
O80.3764 (4)0.0677 (5)0.8472 (3)0.127 (2)
O1w0.3840 (4)0.1235 (4)0.1080 (2)0.085 (1)
O2w0.2475 (3)0.0125 (4)0.0029 (3)0.093 (1)
N10.4509 (2)0.6010 (2)0.1668 (2)0.042 (1)
N20.6282 (2)0.4644 (2)0.1680 (2)0.040 (1)
N30.5886 (2)0.6203 (2)0.3489 (2)0.037 (1)
N40.5589 (2)0.4049 (2)0.3593 (2)0.039 (1)
N50.0616 (3)0.5353 (3)0.1776 (2)0.051 (1)
N60.0083 (3)0.6193 (3)0.1321 (2)0.053 (1)
N70.1622 (4)0.0242 (3)0.4689 (2)0.068 (1)
N80.1719 (3)0.0311 (3)0.5606 (2)0.065 (1)
C10.3589 (3)0.6702 (3)0.1737 (3)0.052 (1)
C20.3424 (4)0.7516 (4)0.1126 (3)0.067 (1)
C30.4204 (4)0.7602 (4)0.0412 (3)0.071 (1)
C40.5140 (4)0.6874 (4)0.0330 (3)0.059 (1)
C50.5273 (3)0.6092 (3)0.0968 (2)0.040 (1)
C60.6252 (3)0.5288 (3)0.0954 (2)0.040 (1)
C70.7086 (3)0.5181 (3)0.0268 (2)0.053 (1)
C80.7974 (4)0.4412 (4)0.0351 (3)0.065 (1)
C90.8013 (4)0.3775 (4)0.1084 (3)0.062 (1)
C100.7147 (3)0.3902 (3)0.1735 (3)0.054 (1)
C110.6043 (3)0.7274 (3)0.3376 (2)0.047 (1)
C120.6689 (4)0.7973 (3)0.3994 (3)0.056 (1)
C130.7193 (4)0.7531 (4)0.4754 (3)0.060 (1)
C140.7031 (3)0.6426 (3)0.4878 (2)0.051 (1)
C150.6387 (3)0.5772 (3)0.4236 (2)0.038 (1)
C160.6185 (3)0.4573 (3)0.4303 (2)0.038 (1)
C170.6543 (3)0.3993 (3)0.5058 (2)0.050 (1)
C180.6304 (4)0.2878 (4)0.5069 (3)0.057 (1)
C190.5730 (4)0.2352 (3)0.4345 (3)0.060 (1)
C200.5375 (3)0.2961 (3)0.3608 (3)0.052 (1)
C210.2764 (3)0.3865 (3)0.2407 (2)0.042 (1)
C220.1502 (3)0.3394 (3)0.2619 (3)0.051 (1)
C230.0166 (3)0.5229 (3)0.2579 (2)0.046 (1)
C240.0744 (3)0.6675 (3)0.1779 (2)0.048 (1)
C250.1228 (4)0.7735 (4)0.0238 (3)0.070 (1)
C260.0095 (5)0.8339 (4)0.0065 (4)0.075 (1)
C270.2863 (5)0.0303 (4)0.2961 (4)0.060 (2)0.735 (6)
C280.1531 (6)0.0030 (6)0.2749 (7)0.061 (2)0.735 (6)
C27'0.317 (2)0.026 (1)0.302 (2)0.060 (2)0.265 (6)
C28'0.181 (2)0.009 (2)0.291 (3)0.061 (2)0.265 (6)
C290.1120 (4)0.1115 (3)0.4291 (3)0.057 (1)
C300.1304 (3)0.1234 (3)0.5893 (3)0.052 (1)
C310.1983 (4)0.0411 (4)0.7600 (3)0.062 (1)
C320.3376 (4)0.0433 (4)0.7732 (3)0.062 (1)
H3o0.11120.92120.03870.107*
H7o0.47630.01680.72540.132*
H1w10.450 (3)0.095 (4)0.126 (3)0.102*
H1w20.357 (4)0.164 (4)0.150 (2)0.102*
H2w10.272 (5)0.029 (5)0.056 (2)0.111*
H2w20.302 (4)0.029 (4)0.025 (3)0.111*
H10.30480.66300.22100.062*
H20.27940.80020.11950.081*
H30.41030.81420.00100.085*
H40.56710.69140.01520.071*
H70.70480.56170.02360.063*
H80.85480.43310.00990.078*
H90.86140.32600.11460.074*
H100.71640.34540.22330.065*
H110.57040.75690.28590.056*
H120.67780.87210.38960.067*
H130.76380.79750.51800.072*
H140.73550.61170.53950.061*
H170.69400.43590.55520.060*
H180.65360.24860.55710.068*
H190.55740.15970.43410.071*
H200.49770.26010.31120.062*
H22a0.16030.26990.29070.061*
H22b0.10540.32390.20500.061*
H25a0.11690.69760.00340.084*
H25b0.19160.80230.00950.084*
H28a0.14090.00290.20970.074*0.735 (6)
H28b0.10330.05400.30030.074*0.735 (6)
H28c0.16250.01360.22970.074*0.265 (6)
H28d0.15810.04940.33250.074*0.265 (6)
H31a0.17840.02260.72570.074*
H31b0.16160.03310.81880.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0341 (2)0.0451 (2)0.0334 (2)0.0016 (2)0.0003 (2)0.0052 (2)
S10.0427 (5)0.0736 (7)0.0511 (5)0.0029 (4)0.0053 (4)0.0165 (4)
S20.0465 (5)0.0635 (6)0.0528 (5)0.0018 (4)0.0139 (4)0.0034 (4)
S30.0590 (6)0.0574 (6)0.0755 (7)0.0155 (5)0.0013 (5)0.0055 (5)
S40.0825 (8)0.0728 (8)0.0637 (6)0.0280 (6)0.0098 (6)0.0066 (5)
S50.0574 (6)0.0520 (6)0.0734 (6)0.0129 (4)0.0058 (5)0.0001 (5)
S60.0657 (6)0.0587 (6)0.0663 (6)0.0082 (5)0.0068 (5)0.0111 (5)
O10.036 (1)0.057 (2)0.040 (1)0.005 (1)0.001 (1)0.002 (1)
O20.059 (2)0.064 (2)0.054 (2)0.003 (1)0.010 (1)0.005 (1)
O30.080 (2)0.083 (3)0.105 (3)0.000 (2)0.012 (2)0.018 (2)
O40.139 (4)0.106 (3)0.097 (3)0.008 (3)0.039 (3)0.009 (2)
O50.077 (3)0.051 (3)0.094 (3)0.008 (2)0.000 (2)0.002 (2)
O60.074 (3)0.053 (3)0.105 (4)0.009 (2)0.006 (3)0.003 (2)
O5'0.077 (3)0.051 (3)0.094 (3)0.008 (2)0.000 (2)0.002 (2)
O6'0.074 (3)0.053 (3)0.105 (4)0.009 (2)0.006 (3)0.003 (2)
O70.057 (2)0.175 (5)0.101 (3)0.014 (2)0.000 (2)0.026 (3)
O80.069 (2)0.224 (6)0.090 (3)0.013 (3)0.018 (2)0.046 (3)
O1w0.081 (2)0.098 (3)0.076 (2)0.005 (2)0.013 (2)0.002 (2)
O2w0.073 (2)0.089 (3)0.114 (3)0.008 (2)0.008 (2)0.008 (2)
N10.040 (1)0.045 (2)0.040 (1)0.001 (1)0.004 (1)0.003 (1)
N20.037 (1)0.047 (2)0.036 (1)0.002 (1)0.002 (1)0.000 (1)
N30.036 (1)0.044 (2)0.031 (1)0.001 (1)0.001 (1)0.003 (1)
N40.035 (1)0.044 (2)0.039 (1)0.001 (1)0.004 (1)0.006 (1)
N50.040 (2)0.066 (2)0.049 (2)0.012 (1)0.006 (1)0.009 (1)
N60.046 (2)0.067 (2)0.046 (2)0.011 (1)0.005 (1)0.004 (1)
N70.082 (2)0.060 (2)0.060 (2)0.024 (2)0.004 (2)0.007 (2)
N80.071 (2)0.055 (2)0.067 (2)0.018 (2)0.002 (2)0.004 (2)
C10.047 (2)0.056 (2)0.053 (2)0.014 (2)0.003 (2)0.005 (2)
C20.066 (3)0.059 (3)0.078 (3)0.018 (2)0.013 (2)0.007 (2)
C30.074 (3)0.069 (3)0.073 (3)0.009 (2)0.002 (2)0.034 (2)
C40.058 (2)0.064 (3)0.057 (2)0.004 (2)0.001 (2)0.019 (2)
C50.039 (2)0.049 (2)0.032 (1)0.008 (1)0.006 (1)0.002 (1)
C60.040 (2)0.048 (2)0.030 (1)0.006 (1)0.003 (1)0.003 (1)
C70.052 (2)0.068 (3)0.037 (2)0.013 (2)0.007 (2)0.002 (2)
C80.050 (2)0.089 (3)0.055 (2)0.001 (2)0.020 (2)0.019 (2)
C90.047 (2)0.079 (3)0.060 (2)0.015 (2)0.007 (2)0.011 (2)
C100.052 (2)0.062 (2)0.048 (2)0.015 (2)0.002 (2)0.002 (2)
C110.049 (2)0.049 (2)0.043 (2)0.008 (2)0.000 (2)0.003 (1)
C120.062 (2)0.047 (2)0.056 (2)0.012 (2)0.005 (2)0.002 (2)
C130.054 (2)0.071 (3)0.052 (2)0.015 (2)0.003 (2)0.014 (2)
C140.047 (2)0.067 (3)0.038 (2)0.000 (2)0.007 (2)0.001 (2)
C150.030 (1)0.053 (2)0.031 (1)0.002 (1)0.005 (1)0.002 (1)
C160.028 (1)0.053 (2)0.033 (1)0.007 (1)0.007 (1)0.005 (1)
C170.047 (2)0.065 (2)0.040 (2)0.015 (2)0.004 (2)0.010 (2)
C180.056 (2)0.067 (3)0.051 (2)0.021 (2)0.010 (2)0.022 (2)
C190.058 (2)0.047 (2)0.075 (3)0.009 (2)0.014 (2)0.018 (2)
C200.052 (2)0.047 (2)0.057 (2)0.002 (2)0.000 (2)0.007 (2)
C210.039 (2)0.049 (2)0.038 (2)0.002 (1)0.003 (1)0.012 (1)
C220.044 (2)0.052 (2)0.056 (2)0.005 (2)0.003 (2)0.007 (2)
C230.032 (2)0.057 (2)0.048 (2)0.002 (1)0.002 (2)0.001 (2)
C240.042 (2)0.053 (2)0.049 (2)0.001 (2)0.001 (2)0.003 (2)
C250.073 (3)0.065 (3)0.073 (3)0.007 (2)0.014 (2)0.014 (2)
C260.085 (3)0.050 (3)0.090 (3)0.015 (2)0.020 (3)0.004 (2)
C270.064 (4)0.058 (4)0.058 (3)0.001 (3)0.001 (3)0.009 (3)
C280.066 (4)0.069 (3)0.048 (5)0.005 (3)0.017 (3)0.007 (2)
C27'0.064 (4)0.058 (4)0.058 (3)0.001 (3)0.001 (3)0.009 (3)
C28'0.066 (4)0.069 (3)0.048 (5)0.005 (3)0.017 (3)0.007 (2)
C290.052 (2)0.053 (2)0.065 (2)0.006 (2)0.002 (2)0.001 (2)
C300.043 (2)0.053 (2)0.059 (2)0.001 (2)0.004 (2)0.001 (2)
C310.061 (2)0.062 (3)0.061 (2)0.008 (2)0.002 (2)0.006 (2)
C320.058 (2)0.064 (3)0.064 (2)0.001 (2)0.004 (2)0.003 (2)
Geometric parameters (Å, º) top
Cu1—O12.001 (2)C8—C91.354 (6)
Cu1—N11.972 (3)C9—C101.375 (5)
Cu1—N22.045 (3)C11—C121.387 (5)
Cu1—N32.157 (3)C12—C131.373 (6)
Cu1—N41.994 (3)C13—C141.371 (6)
S1—C231.737 (4)C14—C151.378 (5)
S1—C221.807 (4)C15—C161.478 (5)
S2—C231.738 (3)C16—C171.395 (4)
S2—C241.744 (4)C17—C181.376 (6)
S3—C241.733 (4)C18—C191.353 (6)
S3—C251.797 (5)C19—C201.393 (5)
S4—C291.740 (4)C21—C221.514 (5)
S4—C281.782 (5)C25—C261.499 (7)
S4—C28'1.783 (9)C27—C281.514 (8)
S5—C291.731 (4)C27'—C28'1.52 (1)
S5—C301.739 (4)C31—C321.528 (6)
S6—C301.746 (4)O3—H3o0.85
S6—C311.811 (5)O7—H7o0.85
O1—C211.262 (4)O1w—H1w10.85 (1)
O2—C211.239 (4)O1w—H1w20.85 (1)
O3—C261.286 (6)O2w—H2w10.86 (1)
O4—C261.181 (6)O2w—H2w20.86 (1)
O5—C271.228 (5)C1—H10.93
O6—C271.280 (5)C2—H20.93
O5'—C27'1.256 (8)C3—H30.93
O6'—C27'1.242 (9)C4—H40.93
O7—C321.227 (5)C7—H70.93
O8—C321.211 (6)C8—H80.93
N1—C11.341 (4)C9—H90.93
N1—C51.348 (4)C10—H100.93
N2—C101.335 (4)C11—H110.93
N2—C61.350 (4)C12—H120.93
N3—C111.327 (4)C13—H130.93
N3—C151.349 (4)C14—H140.93
N4—C201.340 (5)C17—H170.93
N4—C161.348 (4)C18—H180.93
N5—C231.307 (4)C19—H190.93
N5—N61.382 (4)C20—H200.93
N6—C241.291 (4)C22—H22a0.97
N7—C291.295 (5)C22—H22b0.97
N7—N81.360 (5)C25—H25a0.97
N8—C301.285 (5)C25—H25b0.97
C1—C21.378 (6)C28—H28a0.97
C2—C31.376 (6)C28—H28b0.97
C3—C41.384 (6)C28'—H28c0.97
C4—C51.371 (5)C28'—H28d0.97
C5—C61.478 (5)C31—H31a0.97
C6—C71.386 (5)C31—H31b0.97
C7—C81.380 (6)
O1—Cu1—N194.0 (1)O6—C27—C28115.3 (6)
O1—Cu1—N2143.8 (1)C27—C28—S4119.3 (4)
O1—Cu1—N3113.7 (1)O6'—C27'—O5'127 (2)
O1—Cu1—N490.9 (1)O6'—C27'—C28'122 (1)
N1—Cu1—N280.7 (1)O5'—C27'—C28'111 (1)
N1—Cu1—N394.9 (1)C27'—C28'—S4111 (1)
N1—Cu1—N4173.3 (1)N7—C29—S5113.4 (3)
N2—Cu1—N3102.4 (1)N7—C29—S4124.6 (3)
N2—Cu1—N497.9 (1)S5—C29—S4122.0 (2)
N3—Cu1—N479.0 (1)N8—C30—S5113.5 (3)
C23—S1—C22100.2 (2)N8—C30—S6126.1 (3)
C23—S2—C2486.6 (2)S5—C30—S6120.3 (2)
C24—S3—C25100.0 (2)C32—C31—S6113.5 (3)
C29—S4—C28100.6 (4)O8—C32—O7125.2 (5)
C29—S4—C28'93 (1)O8—C32—C31116.9 (4)
C29—S5—C3086.6 (2)O7—C32—C31117.8 (4)
C30—S6—C31101.5 (2)C26—O3—H3o109.5
C21—O1—Cu1110.5 (2)C32—O7—H7o109.5
C1—N1—C5119.2 (3)H1w1—O1w—H1w2110 (2)
C1—N1—Cu1124.4 (2)H2w1—O2w—H2w2109 (2)
C5—N1—Cu1116.0 (2)N1—C1—H1119.2
C10—N2—C6118.7 (3)C2—C1—H1119.2
C10—N2—Cu1127.4 (2)C3—C2—H2120.5
C6—N2—Cu1113.8 (2)C1—C2—H2120.5
C11—N3—C15118.5 (3)C2—C3—H3120.4
C11—N3—Cu1129.1 (2)C4—C3—H3120.4
C15—N3—Cu1112.4 (2)C5—C4—H4120.5
C20—N4—C16119.3 (3)C3—C4—H4120.5
C20—N4—Cu1123.3 (2)C8—C7—H7120.8
C16—N4—Cu1117.3 (2)C6—C7—H7120.8
C23—N5—N6112.3 (3)C9—C8—H8119.9
C24—N6—N5113.3 (3)C7—C8—H8119.9
C29—N7—N8113.3 (4)C8—C9—H9120.6
C30—N8—N7113.2 (3)C10—C9—H9120.6
N1—C1—C2121.7 (4)N2—C10—H10118.7
C3—C2—C1119.1 (4)C9—C10—H10118.7
C2—C3—C4119.3 (4)N3—C11—H11118.4
C5—C4—C3119.0 (4)C12—C11—H11118.4
N1—C5—C4121.7 (3)C13—C12—H12120.9
N1—C5—C6114.8 (3)C11—C12—H12120.9
C4—C5—C6123.5 (3)C14—C13—H13120.4
N2—C6—C7121.3 (3)C12—C13—H13120.4
N2—C6—C5114.3 (3)C13—C14—H14120.0
C7—C6—C5124.4 (3)C15—C14—H14120.0
C8—C7—C6118.4 (4)C18—C17—H17120.2
C9—C8—C7120.2 (4)C16—C17—H17120.2
C8—C9—C10118.8 (4)C19—C18—H18120.1
N2—C10—C9122.5 (4)C17—C18—H18120.1
N3—C11—C12123.1 (3)C18—C19—H19120.5
C13—C12—C11118.1 (4)C20—C19—H19120.5
C14—C13—C12119.1 (4)N4—C20—H20119.1
C13—C14—C15120.0 (3)C19—C20—H20119.1
N3—C15—C14121.2 (3)C21—C22—H22a108.1
N3—C15—C16115.1 (3)S1—C22—H22a108.1
C14—C15—C16123.8 (3)C21—C22—H22b108.1
N4—C16—C17120.4 (3)S1—C22—H22b108.1
N4—C16—C15116.1 (3)H22a—C22—H22b107.3
C17—C16—C15123.5 (3)C26—C25—H25a106.8
C18—C17—C16119.6 (4)S3—C25—H25a106.8
C19—C18—C17119.8 (3)C26—C25—H25b106.8
C18—C19—C20119.0 (4)S3—C25—H25b106.8
N4—C20—C19121.9 (4)H25a—C25—H25b106.6
O2—C21—O1125.0 (3)C27—C28—H28a107.5
O2—C21—C22116.9 (3)S4—C28—H28a107.5
O1—C21—C22117.9 (3)C27—C28—H28b107.5
C21—C22—S1116.9 (3)S4—C28—H28b107.5
N5—C23—S1125.7 (3)H28a—C28—H28b107.0
N5—C23—S2113.9 (3)C27'—C28'—H28c109.4
S1—C23—S2120.3 (2)S4—C28'—H28c109.4
N6—C24—S3126.1 (3)C27'—C28'—H28d109.4
N6—C24—S2113.8 (3)S4—C28'—H28d109.4
S3—C24—S2120.0 (2)H28c—C28'—H28d108.0
C26—C25—S3122.3 (4)C32—C31—H31a108.9
O4—C26—O3126.0 (6)S6—C31—H31a108.9
O4—C26—C25121.3 (5)C32—C31—H31b108.9
O3—C26—C25112.7 (5)S6—C31—H31b108.9
O5—C27—O6125.6 (6)H31a—C31—H31b107.7
O5—C27—C28119.1 (6)
N1—Cu1—O1—C2185.4 (2)C11—N3—C15—C141.1 (4)
N4—Cu1—O1—C2199.1 (2)Cu1—N3—C15—C14179.0 (2)
N2—Cu1—O1—C215.7 (3)C11—N3—C15—C16179.2 (3)
N3—Cu1—O1—C21177.4 (2)Cu1—N3—C15—C161.3 (3)
O1—Cu1—N1—C137.7 (3)C13—C14—C15—N31.4 (5)
N2—Cu1—N1—C1178.4 (3)C13—C14—C15—C16178.9 (3)
N3—Cu1—N1—C176.5 (3)C20—N4—C16—C171.9 (4)
O1—Cu1—N1—C5149.8 (2)Cu1—N4—C16—C17174.0 (2)
N2—Cu1—N1—C55.9 (2)C20—N4—C16—C15180.0 (3)
N3—Cu1—N1—C596.0 (2)Cu1—N4—C16—C154.2 (3)
N1—Cu1—N2—C10178.2 (3)N3—C15—C16—N43.5 (4)
N4—Cu1—N2—C108.4 (3)C14—C15—C16—N4176.7 (3)
O1—Cu1—N2—C1094.2 (3)N3—C15—C16—C17174.5 (3)
N3—Cu1—N2—C1088.8 (3)C14—C15—C16—C175.2 (5)
N1—Cu1—N2—C63.3 (2)N4—C16—C17—C181.2 (5)
N4—Cu1—N2—C6170.1 (2)C15—C16—C17—C18179.2 (3)
O1—Cu1—N2—C687.4 (3)C16—C17—C18—C190.3 (5)
N3—Cu1—N2—C689.6 (2)C17—C18—C19—C201.0 (6)
N1—Cu1—N3—C110.3 (3)C16—N4—C20—C191.2 (5)
N4—Cu1—N3—C11177.0 (3)Cu1—N4—C20—C19174.4 (3)
O1—Cu1—N3—C1196.9 (3)C18—C19—C20—N40.2 (6)
N2—Cu1—N3—C1181.2 (3)Cu1—O1—C21—O23.1 (4)
N1—Cu1—N3—C15177.9 (2)Cu1—O1—C21—C22172.9 (2)
N4—Cu1—N3—C150.62 (19)O2—C21—C22—S1163.0 (3)
O1—Cu1—N3—C1585.5 (2)O1—C21—C22—S120.7 (4)
N2—Cu1—N3—C1596.4 (2)C23—S1—C22—C2173.0 (3)
O1—Cu1—N4—C2064.3 (3)N6—N5—C23—S1177.6 (3)
N2—Cu1—N4—C2080.4 (3)N6—N5—C23—S20.1 (4)
N3—Cu1—N4—C20178.3 (3)C22—S1—C23—N58.3 (4)
O1—Cu1—N4—C16111.3 (2)C22—S1—C23—S2169.0 (2)
N2—Cu1—N4—C16103.9 (2)C24—S2—C23—N50.0 (3)
N3—Cu1—N4—C162.6 (2)C24—S2—C23—S1177.6 (2)
C23—N5—N6—C240.2 (5)N5—N6—C24—S3177.1 (3)
C29—N7—N8—C300.7 (6)N5—N6—C24—S20.2 (4)
C5—N1—C1—C21.9 (6)C25—S3—C24—N67.6 (4)
Cu1—N1—C1—C2170.3 (3)C25—S3—C24—S2169.5 (2)
N1—C1—C2—C31.8 (7)C23—S2—C24—N60.1 (3)
C1—C2—C3—C40.5 (7)C23—S2—C24—S3177.4 (2)
C2—C3—C4—C50.6 (7)C24—S3—C25—C2683.0 (4)
C1—N1—C5—C40.7 (5)S3—C25—C26—O4179.2 (4)
Cu1—N1—C5—C4172.2 (3)S3—C25—C26—O30.9 (6)
C1—N1—C5—C6179.8 (3)O5—C27—C28—S4142.0 (7)
Cu1—N1—C5—C67.3 (4)O6—C27—C28—S440.7 (10)
C3—C4—C5—N10.6 (6)C29—S4—C28—C2761.8 (8)
C3—C4—C5—C6178.9 (4)O6'—C27'—C28'—S48 (4)
C10—N2—C6—C70.8 (5)O5'—C27'—C28'—S4174 (2)
Cu1—N2—C6—C7179.5 (3)C29—S4—C28'—C27'78 (2)
C10—N2—C6—C5179.1 (3)N8—N7—C29—S50.6 (5)
Cu1—N2—C6—C50.5 (3)N8—N7—C29—S4176.9 (3)
N1—C5—C6—N24.3 (4)C30—S5—C29—N71.2 (3)
C4—C5—C6—N2175.1 (3)C30—S5—C29—S4176.3 (3)
N1—C5—C6—C7175.7 (3)C28—S4—C29—N72.2 (5)
C4—C5—C6—C74.8 (5)C28'—S4—C29—N77.4 (8)
N2—C6—C7—C81.4 (5)C28—S4—C29—S5179.4 (4)
C5—C6—C7—C8178.5 (3)C28'—S4—C29—S5169.8 (7)
C6—C7—C8—C90.6 (6)N7—N8—C30—S51.7 (5)
C7—C8—C9—C100.7 (7)N7—N8—C30—S6178.3 (3)
C6—N2—C10—C90.5 (6)C29—S5—C30—N81.6 (3)
Cu1—N2—C10—C9177.9 (3)C29—S5—C30—S6178.3 (3)
C8—C9—C10—N21.3 (7)C31—S6—C30—N81.7 (4)
C15—N3—C11—C120.6 (5)C31—S6—C30—S5178.3 (2)
Cu1—N3—C11—C12178.1 (3)C30—S6—C31—C3292.5 (3)
N3—C11—C12—C130.3 (6)S6—C31—C32—O8100.3 (5)
C11—C12—C13—C140.6 (6)S6—C31—C32—O779.1 (5)
C12—C13—C14—C151.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w2···O20.85 (1)2.24 (4)2.926 (5)137 (5)
O1w—H1w1···O8i0.85 (1)1.97 (2)2.793 (5)163 (6)
O2w—H2w1···O8ii0.86 (1)1.91 (2)2.733 (6)161 (5)
O2w—H2w2···O1w0.86 (1)1.84 (2)2.673 (5)163 (5)
O3—H3o···O2wiii0.851.802.643 (5)174
O7—H7o···O5i0.851.722.47 (1)146
O7—H7o···O6i0.851.922.680 (6)149
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z1; (iii) x, y+1, z.
 

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