In the title compound, [Cu2(C8H3O7S)(C12H8N2)3(H2O)2]ClO4·3H2O, the 5-sulfonatoisophthalate trianion functions as a bridge between two Cu atoms to form an asymmetric dinuclear cation. One Cu atom is surrounded by four O atoms, two from a 5-sulfonatoisophthalate trianion and two from water ligands, and by two N atoms from a 1,10-phenanthroline ligand. The second Cu atom is bound to two O atoms from a 5-sulfonatoisophthalate trianion and four N atoms from two 1,10-phenanthroline ligands. Both copper centers have a distorted octahedral geometry.
Supporting information
CCDC reference: 282578
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.065
- wR factor = 0.158
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for S1
Alert level C
PLAT213_ALERT_2_C Atom O7 has ADP max/min Ratio ............. 3.30 prolat
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.12 Ratio
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT395_ALERT_2_C Deviating X-O-Y Angle from 120 Deg for O15 149.80 Deg.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.
Diaqua-
κ2O-tris(1,10-phenanthroline)-1
κ2N,
N';2
κ4N,
N'-
µ-5-sulfonatoisophthalato-1:2
κ4O1,
O1':
O3,
O3'-dicopper(II) perchlorate trihydrate
top
Crystal data top
[Cu2(C8H3O7S)(C12H8N2)3(H2O)2]ClO4·3H2O | Z = 2 |
Mr = 1100.39 | F(000) = 1124 |
Triclinic, P1 | Dx = 1.621 Mg m−3 |
Hall symbol: -P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.7224 (9) Å | Cell parameters from 7887 reflections |
b = 15.1064 (12) Å | θ = 1.6–25.1° |
c = 15.2183 (11) Å | µ = 1.13 mm−1 |
α = 117.583 (1)° | T = 298 K |
β = 95.397 (2)° | Block, blue |
γ = 103.732 (1)° | 0.22 × 0.21 × 0.14 mm |
V = 2254.3 (3) Å3 | |
Data collection top
Bruker APEX area-detector diffractometer | 7887 independent reflections |
Radiation source: fine-focus sealed tube | 6173 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 25.1°, θmin = 1.6° |
Absorption correction: numerical (SADABS; Bruker, 2002) | h = −13→12 |
Tmin = 0.78, Tmax = 0.85 | k = −17→18 |
11966 measured reflections | l = −18→17 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0735P)2 + 2.2465P] where P = (Fo2 + 2Fc2)/3 |
7887 reflections | (Δ/σ)max = 0.021 |
651 parameters | Δρmax = 0.67 e Å−3 |
6 restraints | Δρmin = −0.48 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 | 0.22161 (5) | 0.00546 (5) | 0.73381 (4) | 0.03129 (18) | |
Cu2 | −0.01999 (5) | 0.42493 (4) | 1.21359 (4) | 0.03385 (18) | |
S1 | −0.43083 (11) | −0.14274 (10) | 0.81264 (10) | 0.0391 (3) | |
Cl1 | 0.44046 (18) | 0.34622 (15) | 0.73001 (14) | 0.0725 (5) | |
N1 | 0.2928 (4) | −0.0511 (3) | 0.6114 (3) | 0.0372 (10) | |
N2 | 0.1538 (4) | 0.0716 (3) | 0.6614 (3) | 0.0358 (10) | |
N3 | −0.1743 (4) | 0.4280 (3) | 1.1479 (3) | 0.0361 (10) | |
N4 | 0.0517 (4) | 0.5480 (3) | 1.1758 (3) | 0.0384 (10) | |
N5 | −0.0198 (4) | 0.5265 (3) | 1.3619 (3) | 0.0355 (10) | |
N6 | 0.1413 (4) | 0.4371 (3) | 1.2800 (3) | 0.0368 (10) | |
O1 | 0.1223 (3) | 0.0429 (3) | 0.8329 (2) | 0.0365 (8) | |
O2 | −0.0018 (3) | −0.1119 (3) | 0.7146 (3) | 0.0434 (9) | |
O3 | −0.0373 (3) | 0.2849 (2) | 1.0992 (2) | 0.0346 (8) | |
O4 | −0.1588 (3) | 0.2154 (2) | 1.1700 (2) | 0.0369 (8) | |
O5 | −0.4995 (4) | −0.0714 (4) | 0.8403 (5) | 0.0930 (18) | |
O6 | −0.4530 (4) | −0.2084 (4) | 0.8547 (4) | 0.0861 (17) | |
O7 | −0.4411 (4) | −0.1977 (5) | 0.7061 (3) | 0.108 (2) | |
O8 | 0.2811 (3) | −0.0741 (3) | 0.7884 (3) | 0.0511 (10) | |
H8B | 0.3551 | −0.0513 | 0.8060 | 0.077* | |
H8A | 0.2240 | −0.1120 | 0.7953 | 0.077* | |
O9 | 0.3781 (3) | 0.1611 (3) | 0.8353 (3) | 0.0593 (11) | |
H9B | 0.3637 | 0.1931 | 0.8912 | 0.089* | |
H9A | 0.3765 | 0.2021 | 0.8144 | 0.089* | |
O10 | 0.5426 (6) | 0.4170 (7) | 0.7969 (7) | 0.175 (4) | |
O11 | 0.3633 (8) | 0.3173 (6) | 0.7833 (6) | 0.154 (3) | |
O12 | 0.4492 (11) | 0.2686 (10) | 0.6520 (8) | 0.287 (7) | |
O13 | 0.3794 (8) | 0.4010 (8) | 0.6963 (6) | 0.176 (4) | |
O14 | 0.2878 (4) | 0.2179 (4) | 0.0104 (4) | 0.0636 (12) | |
O15 | 0.6521 (6) | 0.6865 (6) | 0.5365 (5) | 0.104 (2) | |
O16 | 0.5996 (6) | 0.1166 (5) | 0.8140 (7) | 0.131 (3) | |
C1 | 0.0215 (4) | −0.0312 (4) | 0.7969 (4) | 0.0308 (11) | |
C2 | −0.0729 (4) | −0.0110 (3) | 0.8575 (3) | 0.0271 (10) | |
C3 | −0.0476 (4) | 0.0819 (3) | 0.9498 (3) | 0.0279 (10) | |
H3 | 0.0297 | 0.1305 | 0.9758 | 0.034* | |
C4 | −0.1358 (4) | 0.1032 (3) | 1.0039 (3) | 0.0269 (10) | |
C5 | −0.2521 (4) | 0.0320 (4) | 0.9640 (3) | 0.0302 (11) | |
H5 | −0.3119 | 0.0450 | 0.9997 | 0.036* | |
C6 | −0.2780 (4) | −0.0591 (4) | 0.8696 (3) | 0.0312 (11) | |
C7 | −0.1893 (4) | −0.0815 (4) | 0.8176 (4) | 0.0299 (11) | |
H7 | −0.2076 | −0.1438 | 0.7557 | 0.036* | |
C8 | −0.1086 (4) | 0.2084 (3) | 1.0997 (3) | 0.0286 (10) | |
C9 | 0.3615 (5) | −0.1119 (5) | 0.5887 (5) | 0.0504 (15) | |
H9 | 0.3838 | −0.1334 | 0.6341 | 0.060* | |
C10 | 0.4022 (6) | −0.1454 (5) | 0.4991 (5) | 0.0614 (17) | |
H10 | 0.4490 | −0.1901 | 0.4846 | 0.074* | |
C11 | 0.3736 (6) | −0.1130 (5) | 0.4329 (5) | 0.0638 (18) | |
H11 | 0.4017 | −0.1341 | 0.3736 | 0.077* | |
C12 | 0.3008 (5) | −0.0469 (5) | 0.4548 (4) | 0.0515 (15) | |
C13 | 0.2670 (6) | −0.0058 (6) | 0.3920 (5) | 0.0672 (19) | |
H13 | 0.2931 | −0.0233 | 0.3320 | 0.081* | |
C14 | 0.1984 (6) | 0.0577 (6) | 0.4184 (5) | 0.0656 (19) | |
H14 | 0.1779 | 0.0834 | 0.3762 | 0.079* | |
C15 | 0.1556 (5) | 0.0871 (5) | 0.5103 (4) | 0.0489 (15) | |
C16 | 0.0821 (6) | 0.1518 (5) | 0.5426 (5) | 0.0591 (17) | |
H16 | 0.0558 | 0.1778 | 0.5025 | 0.071* | |
C17 | 0.0498 (6) | 0.1764 (5) | 0.6321 (5) | 0.0597 (17) | |
H17 | 0.0032 | 0.2209 | 0.6549 | 0.072* | |
C18 | 0.0873 (5) | 0.1341 (4) | 0.6898 (4) | 0.0485 (14) | |
H18 | 0.0641 | 0.1510 | 0.7510 | 0.058* | |
C19 | 0.2625 (4) | −0.0174 (4) | 0.5456 (4) | 0.0390 (12) | |
C20 | 0.1881 (4) | 0.0484 (4) | 0.5723 (4) | 0.0375 (12) | |
C21 | −0.2852 (5) | 0.3666 (4) | 1.1303 (4) | 0.0472 (14) | |
H21 | −0.2958 | 0.3199 | 1.1549 | 0.057* | |
C22 | −0.3861 (5) | 0.3686 (5) | 1.0770 (5) | 0.0545 (16) | |
H22 | −0.4623 | 0.3235 | 1.0659 | 0.065* | |
C23 | −0.3734 (5) | 0.4368 (5) | 1.0411 (5) | 0.0536 (15) | |
H23 | −0.4407 | 0.4381 | 1.0047 | 0.064* | |
C24 | −0.2583 (5) | 0.5052 (4) | 1.0592 (4) | 0.0411 (13) | |
C25 | −0.2373 (6) | 0.5802 (5) | 1.0264 (4) | 0.0522 (15) | |
H25 | −0.3022 | 0.5858 | 0.9914 | 0.063* | |
C26 | −0.1253 (6) | 0.6433 (5) | 1.0450 (4) | 0.0541 (16) | |
H26 | −0.1144 | 0.6930 | 1.0242 | 0.065* | |
C27 | −0.0224 (5) | 0.6361 (4) | 1.0960 (4) | 0.0407 (13) | |
C28 | 0.0958 (6) | 0.6961 (4) | 1.1142 (4) | 0.0525 (15) | |
H28 | 0.1117 | 0.7454 | 1.0929 | 0.063* | |
C29 | 0.1892 (6) | 0.6835 (5) | 1.1632 (5) | 0.0578 (17) | |
H29 | 0.2684 | 0.7252 | 1.1774 | 0.069* | |
C30 | 0.1629 (5) | 0.6067 (4) | 1.1913 (4) | 0.0504 (14) | |
H30 | 0.2266 | 0.5963 | 1.2223 | 0.060* | |
C31 | −0.1605 (5) | 0.4971 (4) | 1.1121 (4) | 0.0342 (11) | |
C32 | −0.0400 (5) | 0.5625 (4) | 1.1297 (3) | 0.0338 (11) | |
C33 | −0.1026 (5) | 0.5687 (4) | 1.4028 (4) | 0.0420 (13) | |
H33 | −0.1769 | 0.5504 | 1.3605 | 0.050* | |
C34 | −0.0816 (6) | 0.6395 (4) | 1.5071 (4) | 0.0482 (15) | |
H34 | −0.1419 | 0.6665 | 1.5332 | 0.058* | |
C35 | 0.0258 (6) | 0.6688 (4) | 1.5696 (4) | 0.0508 (15) | |
H35 | 0.0398 | 0.7168 | 1.6388 | 0.061* | |
C36 | 0.1165 (5) | 0.6275 (4) | 1.5313 (4) | 0.0390 (12) | |
C37 | 0.2344 (6) | 0.6522 (4) | 1.5888 (4) | 0.0504 (15) | |
H37 | 0.2544 | 0.6996 | 1.6586 | 0.061* | |
C38 | 0.3168 (5) | 0.6109 (4) | 1.5474 (4) | 0.0510 (15) | |
H38 | 0.3923 | 0.6302 | 1.5885 | 0.061* | |
C39 | 0.2918 (5) | 0.5368 (4) | 1.4403 (4) | 0.0428 (13) | |
C40 | 0.3726 (5) | 0.4896 (5) | 1.3910 (5) | 0.0506 (15) | |
H40 | 0.4506 | 0.5070 | 1.4270 | 0.061* | |
C41 | 0.3365 (5) | 0.4172 (5) | 1.2890 (5) | 0.0542 (15) | |
H41 | 0.3898 | 0.3848 | 1.2553 | 0.065* | |
C42 | 0.2202 (5) | 0.3924 (4) | 1.2361 (4) | 0.0435 (13) | |
H42 | 0.1966 | 0.3423 | 1.1670 | 0.052* | |
C43 | 0.0882 (5) | 0.5559 (4) | 1.4254 (4) | 0.0342 (11) | |
C44 | 0.1755 (4) | 0.5091 (4) | 1.3813 (4) | 0.0340 (11) | |
H14A | 0.329 (5) | 0.203 (5) | 0.047 (4) | 0.051* | |
H14B | 0.230 (4) | 0.168 (4) | −0.024 (4) | 0.051* | |
H15A | 0.630 (5) | 0.721 (4) | 0.594 (4) | 0.051* | |
H15B | 0.636 (6) | 0.652 (5) | 0.478 (3) | 0.051* | |
H16A | 0.565 (5) | 0.050 (4) | 0.801 (4) | 0.051* | |
H16B | 0.530 (4) | 0.136 (4) | 0.831 (4) | 0.051* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0313 (3) | 0.0385 (3) | 0.0305 (3) | 0.0141 (3) | 0.0110 (3) | 0.0204 (3) |
Cu2 | 0.0342 (4) | 0.0267 (3) | 0.0306 (4) | 0.0074 (3) | −0.0002 (3) | 0.0090 (3) |
S1 | 0.0258 (7) | 0.0369 (7) | 0.0417 (8) | 0.0014 (5) | −0.0027 (6) | 0.0156 (6) |
Cl1 | 0.0748 (12) | 0.0703 (11) | 0.0568 (11) | 0.0059 (10) | 0.0218 (9) | 0.0267 (9) |
N1 | 0.040 (2) | 0.038 (2) | 0.036 (2) | 0.018 (2) | 0.015 (2) | 0.018 (2) |
N2 | 0.036 (2) | 0.037 (2) | 0.036 (2) | 0.0117 (19) | 0.0041 (19) | 0.020 (2) |
N3 | 0.038 (2) | 0.032 (2) | 0.039 (2) | 0.0079 (19) | 0.0059 (19) | 0.020 (2) |
N4 | 0.038 (3) | 0.032 (2) | 0.040 (3) | 0.004 (2) | 0.007 (2) | 0.017 (2) |
N5 | 0.044 (3) | 0.027 (2) | 0.034 (2) | 0.0115 (19) | 0.009 (2) | 0.0142 (19) |
N6 | 0.037 (2) | 0.034 (2) | 0.033 (2) | 0.0135 (19) | 0.0043 (19) | 0.011 (2) |
O1 | 0.0305 (19) | 0.0407 (19) | 0.0316 (19) | 0.0086 (16) | 0.0129 (15) | 0.0132 (16) |
O2 | 0.041 (2) | 0.0349 (19) | 0.037 (2) | 0.0141 (16) | 0.0125 (17) | 0.0034 (17) |
O3 | 0.0374 (19) | 0.0266 (17) | 0.0279 (18) | 0.0027 (15) | 0.0081 (15) | 0.0079 (15) |
O4 | 0.046 (2) | 0.0331 (18) | 0.0299 (19) | 0.0098 (16) | 0.0160 (16) | 0.0144 (16) |
O5 | 0.035 (2) | 0.058 (3) | 0.158 (5) | 0.014 (2) | −0.008 (3) | 0.038 (3) |
O6 | 0.047 (3) | 0.091 (3) | 0.131 (4) | −0.014 (2) | −0.014 (3) | 0.087 (4) |
O7 | 0.047 (3) | 0.136 (5) | 0.042 (3) | −0.024 (3) | −0.010 (2) | −0.004 (3) |
O8 | 0.0295 (19) | 0.078 (3) | 0.076 (3) | 0.016 (2) | 0.016 (2) | 0.062 (3) |
O9 | 0.053 (3) | 0.059 (3) | 0.053 (3) | 0.000 (2) | 0.002 (2) | 0.028 (2) |
O10 | 0.096 (5) | 0.198 (8) | 0.197 (9) | −0.019 (5) | −0.043 (5) | 0.117 (7) |
O11 | 0.194 (8) | 0.130 (6) | 0.204 (8) | 0.070 (6) | 0.125 (7) | 0.112 (6) |
O12 | 0.291 (14) | 0.295 (13) | 0.182 (9) | 0.195 (12) | 0.109 (10) | −0.010 (10) |
O13 | 0.193 (8) | 0.248 (10) | 0.153 (7) | 0.100 (8) | 0.033 (6) | 0.139 (8) |
O14 | 0.063 (3) | 0.060 (3) | 0.053 (3) | 0.007 (2) | −0.009 (2) | 0.027 (2) |
O15 | 0.107 (5) | 0.121 (6) | 0.072 (4) | 0.040 (4) | 0.020 (4) | 0.039 (4) |
O16 | 0.108 (5) | 0.105 (5) | 0.243 (8) | 0.054 (4) | 0.101 (5) | 0.115 (6) |
C1 | 0.029 (3) | 0.038 (3) | 0.030 (3) | 0.013 (2) | 0.008 (2) | 0.019 (2) |
C2 | 0.027 (2) | 0.030 (2) | 0.026 (2) | 0.010 (2) | 0.005 (2) | 0.015 (2) |
C3 | 0.025 (2) | 0.025 (2) | 0.029 (3) | 0.0036 (19) | 0.001 (2) | 0.013 (2) |
C4 | 0.029 (3) | 0.026 (2) | 0.028 (3) | 0.010 (2) | 0.005 (2) | 0.015 (2) |
C5 | 0.028 (3) | 0.034 (3) | 0.029 (3) | 0.009 (2) | 0.007 (2) | 0.017 (2) |
C6 | 0.031 (3) | 0.029 (2) | 0.028 (3) | 0.005 (2) | 0.001 (2) | 0.014 (2) |
C7 | 0.027 (3) | 0.026 (2) | 0.028 (3) | 0.005 (2) | 0.004 (2) | 0.009 (2) |
C8 | 0.029 (3) | 0.025 (2) | 0.026 (3) | 0.007 (2) | 0.003 (2) | 0.010 (2) |
C9 | 0.050 (4) | 0.060 (4) | 0.057 (4) | 0.029 (3) | 0.025 (3) | 0.035 (3) |
C10 | 0.065 (4) | 0.064 (4) | 0.061 (4) | 0.035 (3) | 0.031 (3) | 0.026 (4) |
C11 | 0.055 (4) | 0.080 (5) | 0.047 (4) | 0.018 (4) | 0.028 (3) | 0.023 (4) |
C12 | 0.045 (3) | 0.068 (4) | 0.033 (3) | 0.006 (3) | 0.011 (3) | 0.023 (3) |
C13 | 0.060 (4) | 0.099 (6) | 0.049 (4) | 0.011 (4) | 0.013 (3) | 0.049 (4) |
C14 | 0.065 (4) | 0.087 (5) | 0.052 (4) | 0.002 (4) | −0.003 (3) | 0.053 (4) |
C15 | 0.043 (3) | 0.053 (3) | 0.048 (4) | 0.000 (3) | −0.007 (3) | 0.034 (3) |
C16 | 0.056 (4) | 0.051 (4) | 0.073 (5) | 0.005 (3) | −0.009 (3) | 0.043 (4) |
C17 | 0.062 (4) | 0.040 (3) | 0.077 (5) | 0.021 (3) | 0.003 (4) | 0.029 (3) |
C18 | 0.051 (3) | 0.041 (3) | 0.053 (4) | 0.021 (3) | 0.008 (3) | 0.021 (3) |
C19 | 0.036 (3) | 0.042 (3) | 0.039 (3) | 0.005 (2) | 0.005 (2) | 0.025 (3) |
C20 | 0.032 (3) | 0.041 (3) | 0.034 (3) | 0.003 (2) | 0.001 (2) | 0.020 (2) |
C21 | 0.039 (3) | 0.041 (3) | 0.058 (4) | 0.004 (3) | 0.003 (3) | 0.027 (3) |
C22 | 0.034 (3) | 0.054 (4) | 0.074 (4) | 0.008 (3) | 0.006 (3) | 0.034 (3) |
C23 | 0.042 (3) | 0.067 (4) | 0.057 (4) | 0.025 (3) | 0.005 (3) | 0.033 (3) |
C24 | 0.046 (3) | 0.043 (3) | 0.037 (3) | 0.022 (3) | 0.010 (3) | 0.018 (3) |
C25 | 0.063 (4) | 0.063 (4) | 0.045 (4) | 0.033 (3) | 0.013 (3) | 0.033 (3) |
C26 | 0.085 (5) | 0.053 (4) | 0.049 (4) | 0.035 (4) | 0.026 (3) | 0.037 (3) |
C27 | 0.057 (4) | 0.030 (3) | 0.033 (3) | 0.011 (3) | 0.017 (3) | 0.015 (2) |
C28 | 0.075 (4) | 0.043 (3) | 0.045 (4) | 0.016 (3) | 0.025 (3) | 0.027 (3) |
C29 | 0.058 (4) | 0.049 (4) | 0.052 (4) | −0.001 (3) | 0.015 (3) | 0.023 (3) |
C30 | 0.046 (3) | 0.049 (3) | 0.050 (4) | 0.008 (3) | 0.009 (3) | 0.024 (3) |
C31 | 0.043 (3) | 0.033 (3) | 0.029 (3) | 0.019 (2) | 0.014 (2) | 0.013 (2) |
C32 | 0.046 (3) | 0.027 (2) | 0.023 (3) | 0.010 (2) | 0.010 (2) | 0.009 (2) |
C33 | 0.048 (3) | 0.034 (3) | 0.050 (3) | 0.017 (3) | 0.014 (3) | 0.024 (3) |
C34 | 0.068 (4) | 0.033 (3) | 0.053 (4) | 0.027 (3) | 0.031 (3) | 0.022 (3) |
C35 | 0.081 (5) | 0.030 (3) | 0.037 (3) | 0.019 (3) | 0.017 (3) | 0.012 (3) |
C36 | 0.059 (4) | 0.027 (3) | 0.029 (3) | 0.011 (2) | 0.007 (3) | 0.014 (2) |
C37 | 0.066 (4) | 0.033 (3) | 0.030 (3) | 0.001 (3) | −0.007 (3) | 0.009 (2) |
C38 | 0.049 (4) | 0.045 (3) | 0.039 (3) | 0.001 (3) | −0.007 (3) | 0.015 (3) |
C39 | 0.041 (3) | 0.038 (3) | 0.040 (3) | 0.002 (2) | −0.002 (2) | 0.018 (3) |
C40 | 0.034 (3) | 0.058 (4) | 0.057 (4) | 0.012 (3) | 0.002 (3) | 0.030 (3) |
C41 | 0.048 (4) | 0.056 (4) | 0.062 (4) | 0.026 (3) | 0.016 (3) | 0.027 (3) |
C42 | 0.046 (3) | 0.044 (3) | 0.035 (3) | 0.019 (3) | 0.008 (3) | 0.013 (3) |
C43 | 0.047 (3) | 0.024 (2) | 0.027 (3) | 0.008 (2) | 0.005 (2) | 0.011 (2) |
C44 | 0.041 (3) | 0.025 (2) | 0.028 (3) | 0.004 (2) | 0.003 (2) | 0.011 (2) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.950 (3) | C10—H10 | 0.9300 |
Cu1—O8 | 1.958 (3) | C11—C12 | 1.408 (9) |
Cu1—N1 | 2.013 (4) | C11—H11 | 0.9300 |
Cu1—N2 | 2.019 (4) | C12—C19 | 1.397 (7) |
Cu1—O9 | 2.309 (4) | C12—C13 | 1.432 (9) |
Cu2—O3 | 1.966 (3) | C13—C14 | 1.342 (10) |
Cu2—N6 | 1.984 (4) | C13—H13 | 0.9300 |
Cu2—N3 | 2.004 (4) | C14—C15 | 1.437 (9) |
Cu2—N5 | 2.059 (4) | C14—H14 | 0.9300 |
Cu2—N4 | 2.198 (4) | C15—C20 | 1.388 (7) |
S1—O6 | 1.398 (4) | C15—C16 | 1.405 (9) |
S1—O7 | 1.415 (5) | C16—C17 | 1.354 (9) |
S1—O5 | 1.429 (5) | C16—H16 | 0.9300 |
S1—C6 | 1.782 (5) | C17—C18 | 1.398 (8) |
Cl1—O12 | 1.259 (8) | C17—H17 | 0.9300 |
Cl1—O10 | 1.330 (7) | C18—H18 | 0.9300 |
Cl1—O11 | 1.394 (6) | C19—C20 | 1.420 (7) |
Cl1—O13 | 1.437 (8) | C21—C22 | 1.385 (8) |
N1—C9 | 1.313 (6) | C21—H21 | 0.9300 |
N1—C19 | 1.371 (6) | C22—C23 | 1.358 (8) |
N2—C18 | 1.312 (6) | C22—H22 | 0.9300 |
N2—C20 | 1.361 (6) | C23—C24 | 1.403 (8) |
N3—C21 | 1.324 (6) | C23—H23 | 0.9300 |
N3—C31 | 1.369 (6) | C24—C31 | 1.401 (7) |
N4—C30 | 1.320 (7) | C24—C25 | 1.417 (8) |
N4—C32 | 1.345 (6) | C25—C26 | 1.341 (8) |
N5—C33 | 1.333 (6) | C25—H25 | 0.9300 |
N5—C43 | 1.356 (6) | C26—C27 | 1.426 (8) |
N6—C42 | 1.324 (6) | C26—H26 | 0.9300 |
N6—C44 | 1.358 (6) | C27—C28 | 1.385 (8) |
O1—C1 | 1.277 (5) | C27—C32 | 1.407 (7) |
O2—C1 | 1.222 (5) | C28—C29 | 1.367 (9) |
O3—C8 | 1.260 (5) | C28—H28 | 0.9300 |
O4—C8 | 1.242 (5) | C29—C30 | 1.392 (8) |
O8—H8B | 0.8200 | C29—H29 | 0.9300 |
O8—H8A | 0.8200 | C30—H30 | 0.9300 |
O9—H9B | 0.8200 | C31—C32 | 1.437 (7) |
O9—H9A | 0.8200 | C33—C34 | 1.397 (7) |
O14—H14A | 0.84 (4) | C33—H33 | 0.9300 |
O14—H14B | 0.79 (4) | C34—C35 | 1.344 (8) |
O15—H15A | 0.88 (4) | C34—H34 | 0.9300 |
O15—H15B | 0.76 (4) | C35—C36 | 1.398 (8) |
O16—H16A | 0.91 (4) | C35—H35 | 0.9300 |
O16—H16B | 0.95 (4) | C36—C43 | 1.412 (7) |
C1—C2 | 1.504 (6) | C36—C37 | 1.429 (8) |
C2—C7 | 1.386 (6) | C37—C38 | 1.325 (8) |
C2—C3 | 1.389 (6) | C37—H37 | 0.9300 |
C3—C4 | 1.387 (6) | C38—C39 | 1.435 (7) |
C3—H3 | 0.9300 | C38—H38 | 0.9300 |
C4—C5 | 1.388 (6) | C39—C40 | 1.389 (8) |
C4—C8 | 1.509 (6) | C39—C44 | 1.410 (7) |
C5—C6 | 1.392 (6) | C40—C41 | 1.366 (8) |
C5—H5 | 0.9300 | C40—H40 | 0.9300 |
C6—C7 | 1.377 (6) | C41—C42 | 1.385 (8) |
C7—H7 | 0.9300 | C41—H41 | 0.9300 |
C9—C10 | 1.394 (8) | C42—H42 | 0.9300 |
C9—H9 | 0.9300 | C43—C44 | 1.425 (7) |
C10—C11 | 1.356 (9) | | |
| | | |
O1—Cu1—O8 | 90.75 (15) | C14—C13—C12 | 121.1 (6) |
O1—Cu1—N1 | 168.72 (16) | C14—C13—H13 | 119.5 |
O8—Cu1—N1 | 93.07 (17) | C12—C13—H13 | 119.5 |
O1—Cu1—N2 | 93.01 (16) | C13—C14—C15 | 121.6 (6) |
O8—Cu1—N2 | 173.23 (17) | C13—C14—H14 | 119.2 |
N1—Cu1—N2 | 82.21 (17) | C15—C14—H14 | 119.2 |
O1—Cu1—O9 | 92.68 (14) | C20—C15—C16 | 116.8 (6) |
O8—Cu1—O9 | 95.31 (16) | C20—C15—C14 | 118.1 (6) |
N1—Cu1—O9 | 97.53 (16) | C16—C15—C14 | 125.1 (6) |
N2—Cu1—O9 | 90.14 (16) | C17—C16—C15 | 119.9 (6) |
O3—Cu2—N6 | 91.55 (15) | C17—C16—H16 | 120.0 |
O3—Cu2—N3 | 92.23 (15) | C15—C16—H16 | 120.0 |
N6—Cu2—N3 | 173.72 (16) | C16—C17—C18 | 119.2 (6) |
O3—Cu2—N5 | 153.08 (15) | C16—C17—H17 | 120.4 |
N6—Cu2—N5 | 82.01 (17) | C18—C17—H17 | 120.4 |
N3—Cu2—N5 | 96.77 (17) | N2—C18—C17 | 122.7 (6) |
O3—Cu2—N4 | 110.68 (14) | N2—C18—H18 | 118.6 |
N6—Cu2—N4 | 94.24 (17) | C17—C18—H18 | 118.6 |
N3—Cu2—N4 | 79.73 (16) | N1—C19—C12 | 122.2 (5) |
N5—Cu2—N4 | 95.90 (16) | N1—C19—C20 | 117.3 (5) |
O6—S1—O7 | 113.6 (4) | C12—C19—C20 | 120.5 (5) |
O6—S1—O5 | 112.9 (3) | N2—C20—C15 | 123.2 (5) |
O7—S1—O5 | 111.9 (4) | N2—C20—C19 | 116.2 (4) |
O6—S1—C6 | 107.0 (2) | C15—C20—C19 | 120.5 (5) |
O7—S1—C6 | 106.5 (3) | N3—C21—C22 | 123.2 (5) |
O5—S1—C6 | 104.0 (2) | N3—C21—H21 | 118.4 |
O12—Cl1—O10 | 117.3 (7) | C22—C21—H21 | 118.4 |
O12—Cl1—O11 | 113.2 (8) | C23—C22—C21 | 119.6 (5) |
O10—Cl1—O11 | 107.9 (6) | C23—C22—H22 | 120.2 |
O12—Cl1—O13 | 107.8 (8) | C21—C22—H22 | 120.2 |
O10—Cl1—O13 | 106.9 (6) | C22—C23—C24 | 119.7 (5) |
O11—Cl1—O13 | 102.4 (5) | C22—C23—H23 | 120.1 |
C9—N1—C19 | 118.6 (5) | C24—C23—H23 | 120.1 |
C9—N1—Cu1 | 129.6 (4) | C31—C24—C23 | 117.2 (5) |
C19—N1—Cu1 | 111.7 (3) | C31—C24—C25 | 119.4 (5) |
C18—N2—C20 | 118.0 (5) | C23—C24—C25 | 123.4 (5) |
C18—N2—Cu1 | 129.4 (4) | C26—C25—C24 | 121.0 (5) |
C20—N2—Cu1 | 112.5 (3) | C26—C25—H25 | 119.5 |
C21—N3—C31 | 117.6 (4) | C24—C25—H25 | 119.5 |
C21—N3—Cu2 | 127.1 (4) | C25—C26—C27 | 121.7 (5) |
C31—N3—Cu2 | 115.1 (3) | C25—C26—H26 | 119.1 |
C30—N4—C32 | 118.2 (5) | C27—C26—H26 | 119.1 |
C30—N4—Cu2 | 132.0 (4) | C28—C27—C32 | 116.7 (5) |
C32—N4—Cu2 | 109.8 (3) | C28—C27—C26 | 124.5 (5) |
C33—N5—C43 | 117.5 (4) | C32—C27—C26 | 118.8 (5) |
C33—N5—Cu2 | 131.9 (4) | C29—C28—C27 | 120.6 (5) |
C43—N5—Cu2 | 110.6 (3) | C29—C28—H28 | 119.7 |
C42—N6—C44 | 118.5 (4) | C27—C28—H28 | 119.7 |
C42—N6—Cu2 | 128.0 (3) | C28—C29—C30 | 118.4 (6) |
C44—N6—Cu2 | 113.1 (3) | C28—C29—H29 | 120.8 |
C1—O1—Cu1 | 108.7 (3) | C30—C29—H29 | 120.8 |
C8—O3—Cu2 | 115.4 (3) | N4—C30—C29 | 123.0 (6) |
Cu1—O8—H8B | 109.5 | N4—C30—H30 | 118.5 |
Cu1—O8—H8A | 109.5 | C29—C30—H30 | 118.5 |
H8B—O8—H8A | 139.9 | N3—C31—C24 | 122.6 (5) |
Cu1—O9—H9B | 109.5 | N3—C31—C32 | 117.7 (4) |
Cu1—O9—H9A | 109.5 | C24—C31—C32 | 119.6 (5) |
H9B—O9—H9A | 100.0 | N4—C32—C27 | 123.0 (5) |
H14A—O14—H14B | 107 (6) | N4—C32—C31 | 117.6 (4) |
H15A—O15—H15B | 150 (7) | C27—C32—C31 | 119.4 (5) |
H16A—O16—H16B | 93 (5) | N5—C33—C34 | 122.2 (5) |
O2—C1—O1 | 122.9 (4) | N5—C33—H33 | 118.9 |
O2—C1—C2 | 120.5 (4) | C34—C33—H33 | 118.9 |
O1—C1—C2 | 116.4 (4) | C35—C34—C33 | 120.1 (5) |
C7—C2—C3 | 119.2 (4) | C35—C34—H34 | 119.9 |
C7—C2—C1 | 119.9 (4) | C33—C34—H34 | 119.9 |
C3—C2—C1 | 120.7 (4) | C34—C35—C36 | 120.4 (5) |
C4—C3—C2 | 121.0 (4) | C34—C35—H35 | 119.8 |
C4—C3—H3 | 119.5 | C36—C35—H35 | 119.8 |
C2—C3—H3 | 119.5 | C35—C36—C43 | 116.2 (5) |
C3—C4—C5 | 119.6 (4) | C35—C36—C37 | 126.2 (5) |
C3—C4—C8 | 119.8 (4) | C43—C36—C37 | 117.6 (5) |
C5—C4—C8 | 120.3 (4) | C38—C37—C36 | 123.1 (5) |
C4—C5—C6 | 119.1 (4) | C38—C37—H37 | 118.4 |
C4—C5—H5 | 120.4 | C36—C37—H37 | 118.4 |
C6—C5—H5 | 120.4 | C37—C38—C39 | 121.3 (5) |
C7—C6—C5 | 121.1 (4) | C37—C38—H38 | 119.3 |
C7—C6—S1 | 120.0 (3) | C39—C38—H38 | 119.3 |
C5—C6—S1 | 118.7 (4) | C40—C39—C44 | 117.7 (5) |
C6—C7—C2 | 119.9 (4) | C40—C39—C38 | 125.0 (5) |
C6—C7—H7 | 120.0 | C44—C39—C38 | 117.2 (5) |
C2—C7—H7 | 120.0 | C41—C40—C39 | 119.5 (5) |
O4—C8—O3 | 124.8 (4) | C41—C40—H40 | 120.3 |
O4—C8—C4 | 120.3 (4) | C39—C40—H40 | 120.3 |
O3—C8—C4 | 114.8 (4) | C40—C41—C42 | 119.7 (5) |
N1—C9—C10 | 122.4 (6) | C40—C41—H41 | 120.2 |
N1—C9—H9 | 118.8 | C42—C41—H41 | 120.2 |
C10—C9—H9 | 118.8 | N6—C42—C41 | 122.6 (5) |
C11—C10—C9 | 120.0 (6) | N6—C42—H42 | 118.7 |
C11—C10—H10 | 120.0 | C41—C42—H42 | 118.7 |
C9—C10—H10 | 120.0 | N5—C43—C36 | 123.6 (5) |
C10—C11—C12 | 119.5 (6) | N5—C43—C44 | 117.1 (4) |
C10—C11—H11 | 120.3 | C36—C43—C44 | 119.3 (5) |
C12—C11—H11 | 120.3 | N6—C44—C39 | 121.9 (5) |
C19—C12—C11 | 117.3 (6) | N6—C44—C43 | 116.7 (4) |
C19—C12—C13 | 118.2 (6) | C39—C44—C43 | 121.4 (4) |
C11—C12—C13 | 124.5 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O16—H16B···O9 | 0.95 (4) | 1.90 (4) | 2.843 (8) | 168 (5) |
O15—H15B···O13i | 0.76 (4) | 2.37 (5) | 3.101 (10) | 162 (7) |
O15—H15A···O7ii | 0.88 (4) | 1.99 (4) | 2.858 (8) | 169 (6) |
O14—H14B···O1iii | 0.79 (4) | 2.11 (5) | 2.831 (5) | 151 (6) |
O14—H14A···O6iv | 0.84 (4) | 1.95 (5) | 2.765 (6) | 164 (6) |
O9—H9A···O11 | 0.82 | 2.04 | 2.851 (8) | 171 |
O9—H9B···O14v | 0.82 | 2.01 | 2.793 (7) | 159 |
O8—H8A···O4vi | 0.82 | 1.89 | 2.643 (5) | 152 |
O8—H8B···O5vii | 0.82 | 1.87 | 2.603 (5) | 148 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z; (iii) x, y, z−1; (iv) −x, −y, −z+1; (v) x, y, z+1; (vi) −x, −y, −z+2; (vii) x+1, y, z. |