Cations of the title compound, [Cu(C
5H
4NOS)(C
12H
8N
2)]
2(S
4O
6)·3H
2O, assemble into dimers through paired C—H
S hydrogen bonds, and neighbouring dimers are linked into sheets by hydrogen bonds built from the water molecules and the tetrathionate anions.
Supporting information
CCDC reference: 607472
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.019 Å
- R factor = 0.045
- wR factor = 0.117
- Data-to-parameter ratio = 6.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 19
Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.87
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu2 - S2 .. 5.05 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu2 - O2 .. 6.56 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S3
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S6
PLAT417_ALERT_2_C Short Inter D-H..H-D H35 .. H35 .. 2.14 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. S2 .. 2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19 .. S1 .. 2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22 .. O11 .. 2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. O6 .. 2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H30 .. O4 .. 2.64 Ang.
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 25.01
From the CIF: _reflns_number_total 3657
Count of symmetry unique reflns 3667
Completeness (_total/calc) 99.73%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
16 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
7 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Bis[1-hydroxypyridine-2(1
H)-thionato-
κ2S,
O)(1,10-
phenanthroline
κ2N,
N')copper(II) tetrathionate trihydrate
top
Crystal data top
[Cu(C5H4NOS)(C12H8N2)]2(S4O6)·3H2O | F(000) = 2072 |
Mr = 1018.08 | Dx = 1.696 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 2255 reflections |
a = 26.449 (5) Å | θ = 2.8–21.4° |
b = 14.078 (3) Å | µ = 1.45 mm−1 |
c = 11.802 (2) Å | T = 298 K |
β = 114.882 (3)° | Block, brown |
V = 3986.8 (13) Å3 | 0.35 × 0.29 × 0.24 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3657 independent reflections |
Radiation source: fine-focus sealed tube | 2487 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −31→23 |
Tmin = 0.631, Tmax = 0.723 | k = −16→15 |
10595 measured reflections | l = −13→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0591P)2 + 0.1305P] where P = (Fo2 + 2Fc2)/3 |
3657 reflections | (Δ/σ)max < 0.001 |
532 parameters | Δρmax = 0.58 e Å−3 |
1 restraint | Δρmin = −0.38 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.07267 (4) | 0.37251 (8) | 0.06526 (10) | 0.0389 (3) | |
Cu2 | 0.13984 (5) | 0.44071 (9) | 0.79820 (12) | 0.0512 (4) | |
N1 | 0.0370 (3) | 0.2142 (6) | −0.0916 (8) | 0.0416 (19) | |
N2 | 0.0895 (3) | 0.5062 (6) | 0.1182 (8) | 0.042 (2) | |
N3 | 0.1202 (3) | 0.3464 (5) | 0.2448 (7) | 0.0374 (19) | |
N4 | 0.0995 (3) | 0.5954 (7) | 0.6395 (10) | 0.058 (3) | |
N5 | 0.1828 (3) | 0.4668 (6) | 0.9819 (8) | 0.045 (2) | |
N6 | 0.1533 (3) | 0.3073 (6) | 0.8536 (9) | 0.050 (2) | |
O1 | 0.0646 (3) | 0.2401 (5) | 0.0293 (7) | 0.0484 (18) | |
O2 | 0.1300 (3) | 0.5757 (7) | 0.7637 (8) | 0.079 (3) | |
O3 | 0.2761 (3) | 0.2898 (5) | 0.7862 (8) | 0.064 (2) | |
O4 | 0.2470 (2) | 0.4441 (6) | 0.8197 (7) | 0.062 (2) | |
O5 | 0.3059 (3) | 0.3479 (7) | 0.9961 (7) | 0.085 (3) | |
O6 | 0.3183 (3) | 0.3642 (6) | 0.5496 (6) | 0.0586 (19) | |
O7 | 0.3569 (3) | 0.5085 (6) | 0.5111 (6) | 0.074 (2) | |
O8 | 0.4155 (2) | 0.3969 (5) | 0.6636 (6) | 0.0612 (19) | |
O9 | 0.5051 (3) | 0.3461 (10) | 0.8853 (9) | 0.147 (5) | |
H35 | 0.5249 | 0.3797 | 0.9483 | 0.221* | |
H36 | 0.4787 | 0.3821 | 0.8390 | 0.221* | |
O10 | 0.4449 (4) | 0.4764 (8) | 0.4190 (9) | 0.122 (4) | |
H37 | 0.4183 | 0.4890 | 0.4390 | 0.182* | |
H38 | 0.4296 | 0.4518 | 0.3467 | 0.182* | |
O11 | 0.4126 (3) | 0.3668 (8) | 0.2018 (7) | 0.111 (3) | |
H39 | 0.3806 | 0.3550 | 0.1442 | 0.167* | |
H40 | 0.4358 | 0.3446 | 0.1760 | 0.167* | |
S1 | 0.02702 (11) | 0.39832 (19) | −0.1395 (3) | 0.0468 (6) | |
S2 | 0.08502 (12) | 0.4100 (2) | 0.5974 (3) | 0.0635 (9) | |
S3 | 0.28879 (9) | 0.3709 (2) | 0.8675 (2) | 0.0454 (6) | |
S4 | 0.36505 (9) | 0.4318 (2) | 0.8799 (2) | 0.0473 (6) | |
S5 | 0.34429 (11) | 0.51667 (19) | 0.7301 (3) | 0.0563 (7) | |
S6 | 0.36055 (9) | 0.4353 (2) | 0.5983 (2) | 0.0452 (6) | |
C1 | 0.0180 (4) | 0.2806 (7) | −0.1819 (10) | 0.042 (2) | |
C2 | −0.0092 (4) | 0.2494 (9) | −0.3039 (11) | 0.060 (3) | |
H2 | −0.0230 | 0.2932 | −0.3688 | 0.072* | |
C3 | −0.0161 (5) | 0.1523 (10) | −0.3295 (12) | 0.067 (4) | |
H3 | −0.0339 | 0.1313 | −0.4116 | 0.080* | |
C4 | 0.0034 (4) | 0.0881 (9) | −0.2341 (12) | 0.063 (3) | |
H4 | −0.0017 | 0.0233 | −0.2501 | 0.076* | |
C5 | 0.0300 (4) | 0.1201 (8) | −0.1174 (11) | 0.054 (3) | |
H5 | 0.0441 | 0.0767 | −0.0520 | 0.065* | |
C6 | 0.0742 (4) | 0.5852 (8) | 0.0534 (11) | 0.048 (3) | |
H6 | 0.0516 | 0.5812 | −0.0318 | 0.058* | |
C7 | 0.0906 (5) | 0.6749 (8) | 0.1069 (13) | 0.063 (3) | |
H7 | 0.0781 | 0.7291 | 0.0581 | 0.076* | |
C8 | 0.1248 (5) | 0.6829 (8) | 0.2302 (13) | 0.064 (3) | |
H8 | 0.1362 | 0.7425 | 0.2657 | 0.077* | |
C9 | 0.1428 (4) | 0.6008 (8) | 0.3038 (10) | 0.046 (3) | |
C10 | 0.1238 (4) | 0.5140 (7) | 0.2438 (10) | 0.040 (2) | |
C11 | 0.1395 (3) | 0.4278 (8) | 0.3103 (9) | 0.041 (2) | |
C12 | 0.1747 (3) | 0.4258 (9) | 0.4374 (9) | 0.048 (3) | |
C13 | 0.1892 (4) | 0.3386 (10) | 0.4966 (11) | 0.060 (4) | |
H13 | 0.2126 | 0.3357 | 0.5813 | 0.072* | |
C14 | 0.1694 (4) | 0.2583 (9) | 0.4318 (11) | 0.054 (3) | |
H14 | 0.1791 | 0.1994 | 0.4707 | 0.065* | |
C15 | 0.1339 (4) | 0.2648 (8) | 0.3044 (10) | 0.048 (3) | |
H15 | 0.1195 | 0.2092 | 0.2602 | 0.057* | |
C16 | 0.1789 (4) | 0.5977 (9) | 0.4329 (12) | 0.061 (3) | |
H16 | 0.1929 | 0.6547 | 0.4741 | 0.073* | |
C17 | 0.1937 (5) | 0.5184 (10) | 0.4973 (12) | 0.061 (3) | |
H17 | 0.2165 | 0.5210 | 0.5825 | 0.073* | |
C18 | 0.0767 (4) | 0.5285 (8) | 0.5538 (10) | 0.048 (3) | |
C19 | 0.0453 (5) | 0.5567 (11) | 0.4299 (11) | 0.069 (4) | |
H19 | 0.0287 | 0.5115 | 0.3678 | 0.083* | |
C20 | 0.0394 (5) | 0.6495 (15) | 0.4017 (14) | 0.087 (5) | |
H20 | 0.0181 | 0.6692 | 0.3201 | 0.105* | |
C21 | 0.0648 (6) | 0.7149 (11) | 0.4937 (17) | 0.084 (4) | |
H21 | 0.0610 | 0.7792 | 0.4737 | 0.100* | |
C22 | 0.0947 (6) | 0.6889 (10) | 0.6102 (16) | 0.085 (4) | |
H22 | 0.1123 | 0.7342 | 0.6715 | 0.102* | |
C23 | 0.1978 (4) | 0.5478 (9) | 1.0413 (12) | 0.054 (3) | |
H23 | 0.1865 | 0.6038 | 0.9956 | 0.064* | |
C24 | 0.2293 (5) | 0.5540 (11) | 1.1672 (12) | 0.066 (4) | |
H24 | 0.2376 | 0.6129 | 1.2067 | 0.079* | |
C25 | 0.2482 (4) | 0.4735 (12) | 1.2331 (12) | 0.066 (4) | |
H25 | 0.2711 | 0.4768 | 1.3181 | 0.080* | |
C26 | 0.2335 (4) | 0.3836 (11) | 1.1738 (11) | 0.059 (3) | |
C27 | 0.2006 (3) | 0.3848 (9) | 1.0465 (9) | 0.042 (3) | |
C28 | 0.1845 (4) | 0.3013 (8) | 0.9780 (11) | 0.043 (3) | |
C29 | 0.2025 (5) | 0.2112 (10) | 1.0424 (14) | 0.065 (4) | |
C30 | 0.1856 (5) | 0.1295 (10) | 0.9710 (17) | 0.080 (5) | |
H30 | 0.1968 | 0.0704 | 1.0086 | 0.096* | |
C31 | 0.1532 (5) | 0.1348 (9) | 0.8481 (17) | 0.078 (4) | |
H31 | 0.1401 | 0.0799 | 0.8009 | 0.093* | |
C32 | 0.1393 (4) | 0.2251 (10) | 0.7917 (12) | 0.065 (4) | |
H32 | 0.1189 | 0.2275 | 0.7055 | 0.078* | |
C33 | 0.2523 (5) | 0.2973 (14) | 1.2359 (14) | 0.086 (5) | |
H33 | 0.2757 | 0.2974 | 1.3208 | 0.103* | |
C34 | 0.2369 (5) | 0.2135 (12) | 1.1743 (14) | 0.075 (4) | |
H34 | 0.2489 | 0.1568 | 1.2179 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0387 (6) | 0.0354 (6) | 0.0398 (7) | −0.0029 (6) | 0.0137 (5) | −0.0012 (6) |
Cu2 | 0.0540 (7) | 0.0517 (8) | 0.0462 (8) | 0.0045 (7) | 0.0194 (6) | 0.0034 (7) |
N1 | 0.045 (4) | 0.038 (5) | 0.041 (5) | −0.002 (4) | 0.018 (4) | −0.007 (4) |
N2 | 0.043 (4) | 0.032 (5) | 0.054 (6) | 0.003 (4) | 0.023 (4) | 0.007 (4) |
N3 | 0.036 (4) | 0.033 (5) | 0.039 (5) | −0.004 (3) | 0.011 (3) | −0.007 (4) |
N4 | 0.050 (5) | 0.055 (7) | 0.069 (7) | 0.003 (5) | 0.025 (5) | 0.016 (6) |
N5 | 0.042 (5) | 0.051 (6) | 0.049 (5) | −0.001 (4) | 0.025 (4) | −0.004 (5) |
N6 | 0.046 (5) | 0.041 (5) | 0.073 (7) | −0.001 (4) | 0.035 (5) | −0.011 (5) |
O1 | 0.055 (4) | 0.040 (4) | 0.041 (4) | −0.003 (3) | 0.012 (3) | 0.004 (4) |
O2 | 0.063 (5) | 0.106 (8) | 0.055 (5) | 0.016 (5) | 0.010 (4) | 0.039 (5) |
O3 | 0.052 (4) | 0.056 (5) | 0.082 (6) | −0.002 (4) | 0.026 (4) | −0.010 (4) |
O4 | 0.042 (4) | 0.063 (5) | 0.085 (5) | 0.009 (4) | 0.032 (4) | 0.000 (4) |
O5 | 0.063 (4) | 0.139 (9) | 0.057 (5) | −0.017 (5) | 0.029 (4) | 0.032 (5) |
O6 | 0.063 (4) | 0.055 (5) | 0.051 (4) | −0.013 (4) | 0.017 (3) | −0.006 (4) |
O7 | 0.094 (5) | 0.072 (6) | 0.048 (5) | −0.015 (5) | 0.022 (4) | 0.012 (4) |
O8 | 0.047 (3) | 0.074 (5) | 0.058 (4) | 0.012 (3) | 0.018 (3) | −0.007 (4) |
O9 | 0.065 (5) | 0.240 (15) | 0.100 (7) | −0.002 (7) | 0.000 (5) | 0.089 (9) |
O10 | 0.152 (8) | 0.134 (10) | 0.124 (8) | −0.041 (8) | 0.102 (7) | −0.015 (7) |
O11 | 0.087 (6) | 0.158 (9) | 0.068 (6) | −0.014 (7) | 0.012 (4) | 0.011 (7) |
S1 | 0.0575 (15) | 0.0402 (15) | 0.0402 (13) | 0.0026 (11) | 0.0181 (11) | −0.0010 (11) |
S2 | 0.0727 (18) | 0.060 (2) | 0.0572 (18) | −0.0006 (15) | 0.0267 (15) | −0.0019 (15) |
S3 | 0.0404 (12) | 0.0537 (16) | 0.0449 (14) | −0.0025 (14) | 0.0207 (11) | 0.0015 (16) |
S4 | 0.0399 (12) | 0.0608 (16) | 0.0423 (13) | −0.0061 (13) | 0.0184 (10) | −0.0074 (13) |
S5 | 0.0685 (17) | 0.0358 (14) | 0.077 (2) | 0.0008 (13) | 0.0426 (15) | 0.0013 (14) |
S6 | 0.0439 (13) | 0.0506 (15) | 0.0394 (13) | −0.0045 (14) | 0.0159 (10) | 0.0015 (14) |
C1 | 0.031 (5) | 0.044 (6) | 0.051 (7) | 0.000 (4) | 0.017 (5) | −0.001 (5) |
C2 | 0.064 (7) | 0.062 (8) | 0.051 (8) | −0.013 (6) | 0.020 (6) | −0.024 (6) |
C3 | 0.065 (7) | 0.075 (10) | 0.051 (7) | −0.001 (7) | 0.016 (6) | −0.034 (7) |
C4 | 0.058 (7) | 0.046 (7) | 0.083 (9) | −0.011 (6) | 0.026 (7) | −0.031 (7) |
C5 | 0.057 (6) | 0.031 (6) | 0.072 (8) | −0.002 (5) | 0.025 (6) | −0.005 (6) |
C6 | 0.052 (6) | 0.036 (7) | 0.056 (7) | −0.002 (5) | 0.021 (5) | −0.002 (6) |
C7 | 0.073 (8) | 0.038 (7) | 0.091 (10) | 0.008 (6) | 0.046 (8) | 0.008 (7) |
C8 | 0.067 (8) | 0.043 (7) | 0.091 (10) | −0.016 (6) | 0.042 (8) | −0.014 (7) |
C9 | 0.038 (5) | 0.044 (7) | 0.066 (8) | −0.004 (5) | 0.030 (5) | −0.005 (6) |
C10 | 0.032 (5) | 0.035 (6) | 0.059 (7) | −0.014 (5) | 0.026 (5) | −0.013 (5) |
C11 | 0.034 (5) | 0.048 (7) | 0.051 (6) | −0.005 (5) | 0.026 (5) | −0.003 (6) |
C12 | 0.029 (5) | 0.065 (8) | 0.046 (6) | 0.004 (5) | 0.012 (4) | −0.015 (6) |
C13 | 0.047 (6) | 0.083 (11) | 0.041 (7) | 0.024 (6) | 0.011 (5) | 0.012 (7) |
C14 | 0.059 (7) | 0.048 (7) | 0.051 (8) | 0.011 (6) | 0.019 (6) | 0.008 (6) |
C15 | 0.049 (6) | 0.045 (7) | 0.053 (8) | 0.005 (5) | 0.025 (6) | 0.004 (6) |
C16 | 0.055 (7) | 0.070 (9) | 0.063 (8) | −0.027 (7) | 0.029 (6) | −0.036 (7) |
C17 | 0.054 (7) | 0.072 (9) | 0.053 (7) | −0.011 (7) | 0.018 (6) | −0.018 (8) |
C18 | 0.038 (6) | 0.057 (7) | 0.055 (7) | −0.002 (5) | 0.025 (5) | 0.011 (6) |
C19 | 0.057 (7) | 0.109 (12) | 0.041 (7) | −0.010 (7) | 0.021 (6) | 0.002 (8) |
C20 | 0.075 (9) | 0.138 (15) | 0.063 (9) | 0.027 (10) | 0.043 (8) | 0.045 (11) |
C21 | 0.080 (9) | 0.063 (9) | 0.114 (13) | 0.005 (8) | 0.046 (9) | 0.034 (10) |
C22 | 0.106 (11) | 0.046 (8) | 0.116 (13) | 0.005 (8) | 0.060 (10) | 0.015 (8) |
C23 | 0.052 (7) | 0.048 (8) | 0.070 (9) | −0.008 (6) | 0.035 (7) | −0.008 (6) |
C24 | 0.056 (7) | 0.090 (11) | 0.058 (9) | −0.013 (7) | 0.032 (7) | −0.027 (8) |
C25 | 0.033 (6) | 0.112 (13) | 0.053 (8) | −0.006 (7) | 0.018 (5) | −0.017 (9) |
C26 | 0.049 (6) | 0.083 (9) | 0.057 (7) | 0.008 (7) | 0.032 (5) | 0.018 (8) |
C27 | 0.036 (5) | 0.056 (7) | 0.044 (6) | −0.017 (5) | 0.026 (4) | −0.006 (6) |
C28 | 0.036 (5) | 0.047 (6) | 0.059 (8) | 0.005 (5) | 0.033 (6) | 0.019 (6) |
C29 | 0.056 (7) | 0.060 (9) | 0.104 (12) | 0.009 (7) | 0.057 (8) | 0.016 (8) |
C30 | 0.054 (8) | 0.057 (9) | 0.141 (15) | 0.011 (7) | 0.053 (9) | 0.034 (11) |
C31 | 0.057 (7) | 0.041 (8) | 0.157 (15) | −0.001 (6) | 0.066 (9) | −0.009 (9) |
C32 | 0.046 (6) | 0.071 (10) | 0.079 (10) | 0.000 (6) | 0.029 (6) | −0.010 (8) |
C33 | 0.062 (8) | 0.135 (15) | 0.064 (10) | 0.011 (10) | 0.030 (7) | 0.020 (11) |
C34 | 0.066 (8) | 0.093 (11) | 0.081 (11) | 0.020 (8) | 0.044 (8) | 0.050 (9) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.904 (7) | C6—H6 | 0.9300 |
Cu1—N2 | 1.975 (8) | C7—C8 | 1.356 (15) |
Cu1—N3 | 1.991 (8) | C7—H7 | 0.9300 |
Cu1—S1 | 2.230 (3) | C8—C9 | 1.403 (15) |
Cu2—O2 | 1.938 (10) | C8—H8 | 0.9300 |
Cu2—N6 | 1.971 (9) | C9—C10 | 1.396 (14) |
Cu2—N5 | 2.014 (9) | C9—C16 | 1.419 (15) |
Cu2—S2 | 2.240 (3) | C10—C11 | 1.408 (15) |
N1—C1 | 1.346 (12) | C11—C12 | 1.394 (12) |
N1—O1 | 1.351 (10) | C12—C13 | 1.384 (16) |
N1—C5 | 1.354 (13) | C12—C17 | 1.467 (16) |
N2—C6 | 1.313 (13) | C13—C14 | 1.342 (16) |
N2—C10 | 1.379 (13) | C13—H13 | 0.9300 |
N3—C15 | 1.315 (12) | C14—C15 | 1.400 (15) |
N3—C11 | 1.356 (13) | C14—H14 | 0.9300 |
N4—C18 | 1.326 (14) | C15—H15 | 0.9300 |
N4—C22 | 1.354 (15) | C16—C17 | 1.315 (17) |
N4—O2 | 1.371 (12) | C16—H16 | 0.9300 |
N5—C23 | 1.310 (13) | C17—H17 | 0.9300 |
N5—C27 | 1.354 (13) | C18—C19 | 1.401 (15) |
N6—C32 | 1.336 (15) | C19—C20 | 1.341 (19) |
N6—C28 | 1.351 (13) | C19—H19 | 0.9300 |
O3—S3 | 1.438 (8) | C20—C21 | 1.366 (19) |
O4—S3 | 1.441 (8) | C20—H20 | 0.9300 |
O5—S3 | 1.426 (7) | C21—C22 | 1.317 (19) |
O6—S6 | 1.429 (7) | C21—H21 | 0.9300 |
O7—S6 | 1.431 (7) | C22—H22 | 0.9300 |
O8—S6 | 1.433 (6) | C23—C24 | 1.368 (15) |
O9—H35 | 0.8500 | C23—H23 | 0.9300 |
O9—H36 | 0.8500 | C24—C25 | 1.346 (18) |
O10—H37 | 0.8500 | C24—H24 | 0.9300 |
O10—H38 | 0.8500 | C25—C26 | 1.419 (17) |
O11—H39 | 0.8500 | C25—H25 | 0.9300 |
O11—H40 | 0.8500 | C26—C27 | 1.383 (14) |
S1—C1 | 1.719 (10) | C26—C33 | 1.40 (2) |
S2—C18 | 1.732 (12) | C27—C28 | 1.388 (15) |
S3—S4 | 2.139 (3) | C28—C29 | 1.452 (16) |
S4—S5 | 2.010 (4) | C29—C30 | 1.384 (18) |
S5—S6 | 2.117 (4) | C29—C34 | 1.436 (18) |
C1—C2 | 1.383 (14) | C30—C31 | 1.341 (18) |
C2—C3 | 1.396 (16) | C30—H30 | 0.9300 |
C2—H2 | 0.9300 | C31—C32 | 1.410 (17) |
C3—C4 | 1.365 (16) | C31—H31 | 0.9300 |
C3—H3 | 0.9300 | C32—H32 | 0.9300 |
C4—C5 | 1.334 (15) | C33—C34 | 1.36 (2) |
C4—H4 | 0.9300 | C33—H33 | 0.9300 |
C5—H5 | 0.9300 | C34—H34 | 0.9300 |
C6—C7 | 1.397 (15) | | |
| | | |
O1—Cu1—N2 | 173.4 (3) | C8—C9—C16 | 126.2 (11) |
O1—Cu1—N3 | 91.0 (3) | N2—C10—C9 | 123.2 (10) |
N2—Cu1—N3 | 83.2 (3) | N2—C10—C11 | 115.9 (9) |
O1—Cu1—S1 | 87.7 (2) | C9—C10—C11 | 120.9 (10) |
N2—Cu1—S1 | 97.7 (3) | N3—C11—C12 | 121.1 (10) |
N3—Cu1—S1 | 174.1 (2) | N3—C11—C10 | 117.3 (8) |
O2—Cu2—N6 | 173.5 (4) | C12—C11—C10 | 121.6 (10) |
O2—Cu2—N5 | 90.7 (4) | C13—C12—C11 | 118.6 (10) |
N6—Cu2—N5 | 82.8 (4) | C13—C12—C17 | 125.4 (9) |
O2—Cu2—S2 | 89.8 (3) | C11—C12—C17 | 116.0 (11) |
N6—Cu2—S2 | 96.5 (3) | C14—C13—C12 | 120.1 (10) |
N5—Cu2—S2 | 174.6 (2) | C14—C13—H13 | 120.0 |
C1—N1—O1 | 120.3 (8) | C12—C13—H13 | 120.0 |
C1—N1—C5 | 122.1 (9) | C13—C14—C15 | 118.7 (11) |
O1—N1—C5 | 117.6 (9) | C13—C14—H14 | 120.6 |
C6—N2—C10 | 117.5 (9) | C15—C14—H14 | 120.6 |
C6—N2—Cu1 | 130.5 (8) | N3—C15—C14 | 122.7 (11) |
C10—N2—Cu1 | 112.0 (7) | N3—C15—H15 | 118.6 |
C15—N3—C11 | 118.7 (9) | C14—C15—H15 | 118.6 |
C15—N3—Cu1 | 129.7 (7) | C17—C16—C9 | 123.3 (11) |
C11—N3—Cu1 | 111.6 (6) | C17—C16—H16 | 118.3 |
C18—N4—C22 | 122.1 (12) | C9—C16—H16 | 118.3 |
C18—N4—O2 | 123.1 (10) | C16—C17—C12 | 121.2 (11) |
C22—N4—O2 | 114.8 (12) | C16—C17—H17 | 119.4 |
C23—N5—C27 | 119.1 (9) | C12—C17—H17 | 119.4 |
C23—N5—Cu2 | 129.9 (9) | N4—C18—C19 | 118.3 (11) |
C27—N5—Cu2 | 110.9 (7) | N4—C18—S2 | 119.8 (8) |
C32—N6—C28 | 116.2 (10) | C19—C18—S2 | 121.9 (10) |
C32—N6—Cu2 | 132.4 (9) | C20—C19—C18 | 119.4 (13) |
C28—N6—Cu2 | 111.3 (7) | C20—C19—H19 | 120.3 |
N1—O1—Cu1 | 117.4 (6) | C18—C19—H19 | 120.3 |
N4—O2—Cu2 | 112.9 (7) | C19—C20—C21 | 119.5 (13) |
H35—O9—H36 | 105.6 | C19—C20—H20 | 120.3 |
H37—O10—H38 | 105.1 | C21—C20—H20 | 120.3 |
H39—O11—H40 | 105.6 | C22—C21—C20 | 121.4 (14) |
C1—S1—Cu1 | 96.0 (4) | C22—C21—H21 | 119.3 |
C18—S2—Cu2 | 94.2 (4) | C20—C21—H21 | 119.3 |
O5—S3—O3 | 114.2 (6) | C21—C22—N4 | 119.2 (15) |
O5—S3—O4 | 115.3 (5) | C21—C22—H22 | 120.4 |
O3—S3—O4 | 112.4 (4) | N4—C22—H22 | 120.4 |
O5—S3—S4 | 98.7 (3) | N5—C23—C24 | 123.1 (12) |
O3—S3—S4 | 108.2 (3) | N5—C23—H23 | 118.5 |
O4—S3—S4 | 106.6 (3) | C24—C23—H23 | 118.5 |
S5—S4—S3 | 106.09 (14) | C25—C24—C23 | 118.8 (13) |
S4—S5—S6 | 105.05 (16) | C25—C24—H24 | 120.6 |
O6—S6—O7 | 114.2 (4) | C23—C24—H24 | 120.6 |
O6—S6—O8 | 113.4 (4) | C24—C25—C26 | 120.5 (11) |
O7—S6—O8 | 113.8 (4) | C24—C25—H25 | 119.7 |
O6—S6—S5 | 108.0 (3) | C26—C25—H25 | 119.7 |
O7—S6—S5 | 99.6 (4) | C27—C26—C33 | 120.1 (14) |
O8—S6—S5 | 106.4 (3) | C27—C26—C25 | 116.2 (12) |
N1—C1—C2 | 117.5 (10) | C33—C26—C25 | 123.6 (13) |
N1—C1—S1 | 118.6 (8) | N5—C27—C26 | 122.2 (11) |
C2—C1—S1 | 123.8 (9) | N5—C27—C28 | 116.4 (8) |
C1—C2—C3 | 120.0 (12) | C26—C27—C28 | 121.4 (11) |
C1—C2—H2 | 120.0 | N6—C28—C27 | 118.5 (10) |
C3—C2—H2 | 120.0 | N6—C28—C29 | 122.6 (11) |
C4—C3—C2 | 120.0 (11) | C27—C28—C29 | 118.9 (11) |
C4—C3—H3 | 120.0 | C30—C29—C34 | 125.0 (14) |
C2—C3—H3 | 120.0 | C30—C29—C28 | 117.2 (13) |
C5—C4—C3 | 118.7 (11) | C34—C29—C28 | 117.8 (13) |
C5—C4—H4 | 120.7 | C31—C30—C29 | 120.5 (13) |
C3—C4—H4 | 120.7 | C31—C30—H30 | 119.7 |
C4—C5—N1 | 121.7 (11) | C29—C30—H30 | 119.7 |
C4—C5—H5 | 119.1 | C30—C31—C32 | 118.8 (13) |
N1—C5—H5 | 119.1 | C30—C31—H31 | 120.6 |
N2—C6—C7 | 122.7 (11) | C32—C31—H31 | 120.6 |
N2—C6—H6 | 118.6 | N6—C32—C31 | 124.5 (13) |
C7—C6—H6 | 118.6 | N6—C32—H32 | 117.8 |
C8—C7—C6 | 120.0 (11) | C31—C32—H32 | 117.8 |
C8—C7—H7 | 120.0 | C34—C33—C26 | 121.0 (14) |
C6—C7—H7 | 120.0 | C34—C33—H33 | 119.5 |
C7—C8—C9 | 119.7 (11) | C26—C33—H33 | 119.5 |
C7—C8—H8 | 120.2 | C33—C34—C29 | 120.8 (13) |
C9—C8—H8 | 120.2 | C33—C34—H34 | 119.6 |
C10—C9—C8 | 116.9 (10) | C29—C34—H34 | 119.6 |
C10—C9—C16 | 117.0 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O3 | 0.93 | 2.38 | 3.291 (14) | 166 |
O9—H36···O8 | 0.85 | 2.05 | 2.785 (10) | 144 |
O10—H38···O11 | 0.85 | 1.98 | 2.800 (14) | 163 |
O10—H37···O7 | 0.85 | 2.14 | 2.989 (11) | 172 |
O9—H35···S4i | 0.85 | 2.86 | 3.594 (9) | 146 |
O9—H35···O9i | 0.85 | 2.45 | 2.83 (2) | 108 |
O11—H40···O9ii | 0.85 | 1.98 | 2.785 (12) | 158 |
O11—H39···O5iii | 0.85 | 2.02 | 2.859 (10) | 171 |
C2—H2···S2iv | 0.93 | 2.99 | 3.910 (13) | 170 |
C19—H19···S1iv | 0.93 | 2.94 | 3.856 (14) | 169 |
C21—H21···O8v | 0.93 | 2.57 | 3.331 (15) | 139 |
C22—H22···O11v | 0.93 | 2.64 | 3.406 (17) | 140 |
C8—H8···O6v | 0.93 | 2.63 | 3.499 (15) | 155 |
C24—H24···O3vi | 0.93 | 2.52 | 3.378 (17) | 153 |
C15—H15···S5vii | 0.93 | 2.86 | 3.592 (12) | 136 |
C30—H30···O4viii | 0.93 | 2.64 | 3.520 (16) | 159 |
Symmetry codes: (i) −x+1, y, −z+2; (ii) −x+1, y, −z+1; (iii) x, y, z−1; (iv) −x, y, −z; (v) −x+1/2, y+1/2, −z+1; (vi) −x+1/2, y+1/2, −z+2; (vii) −x+1/2, y−1/2, −z+1; (viii) −x+1/2, y−1/2, −z+2. |