This paper reports a new polymorph of the title compound, [Cu2(C7H5O2)4(C2H6OS)2], a paddlewheel dimer of a tetrabenzoate-bridged dinuclear copper(II) core, with two apically positioned is dordered dimethyl sulfoxide ligands. The Cu—Cu distance is 2.6490 (6)Å.
Supporting information
CCDC reference: 289792
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.046
- wR factor = 0.134
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C51
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C62
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for S2A
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.396 0.552
Tmin(prime) and Tmax expected: 0.468 0.561
RR(prime) = 0.860
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C43
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C61
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu2
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1A
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O10B
PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc.
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
10 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 207
core are coloured gray, while the atoms of ^ ligands are shown in red and
If you require a ^ then it should be escaped
with a \, i.e. \^
Otherwise there must be a matching closing ~, e.g. ^12^C
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), Mercury (Version 1.2.1; Bruno et al., 2002), RasTop (Version 2.0.3) (Valadon, 2004) and POV-RAY
(Version 3.6) (Valadon, 2004); software used to prepare material for publication: WinGX (Farrugia, 1999).
tetra-µ-benzoato-
κ8O:
O'-bis[(dimethyl
sulfoxide-
κO)copper(II)]
top
Crystal data top
[Cu2(C7H5O2)4(C2H6OS)2] | F(000) = 1576 |
Mr = 767.78 | Dx = 1.476 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 35 reflections |
a = 12.0320 (7) Å | θ = 11–17° |
b = 17.0770 (8) Å | µ = 1.41 mm−1 |
c = 17.2590 (11) Å | T = 291 K |
β = 103.040 (5)° | Prismatic, green |
V = 3454.8 (3) Å3 | 0.53 × 0.47 × 0.41 mm |
Z = 4 | |
Data collection top
Philips PW1100 diffractometer | 4830 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Planar graphite monochromator | θmax = 27.0°, θmin = 2.1° |
ω scans | h = −15→14 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→21 |
Tmin = 0.396, Tmax = 0.552 | l = 0→22 |
7794 measured reflections | 4 standard reflections every 120 min |
7550 independent reflections | intensity decay: 3.2% |
Refinement top
Refinement on F2 | 27 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0785P)2 + 0.1835P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.134 | (Δ/σ)max = 0.002 |
S = 1.03 | Δρmax = 0.4 e Å−3 |
7550 reflections | Δρmin = −0.52 e Å−3 |
450 parameters | |
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. Special constraints were applied in the refinement of the disordered
dimethylsulfoxide molecules. For the refinement of the disordered molecules
containing atoms S1A and S1B, the bond distances between pairs of atoms S1A
and C52A, as well as S1B and C52B were set to 1.77 Å (s.u. 0.006 Å), using
the DFIX command. Similarly, distances between atoms O5 and S1A, as
well as O5 and S1B, were set to 1.49 Å (s.u. 0.005 Å). In case of the
disordered molecules containing sulfur atoms S2A and S2B all sulfur-carbon
bond distances were set to be equal within the standard deviation of 0.02 Å
using the SADI command. The same kind of restraint was also applied in case of
sulfur-oxygen, and oxygen-copper distances. The distance between the two
disordered sulfur atoms was set at 1.20 Å, with a standard deviation of 0.01 Å using the DFIX command. Finally, disordered methyl group carbon
atoms C52A and C52B were refined using a restrained anisotropic model achieved
with ISOR command. For the purpose of generating the hydrogen atom positions
on methyl carbon atoms shared between two disordered moieties the coordinates
were calculated in alternate cycles of refinement. Specifically, while
hydrogen atom coordinates corresponding to one disordered set were calculated,
the coordinates of the other set were held constant. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.93074 (4) | 0.30654 (2) | 0.24738 (2) | 0.04185 (13) | |
Cu2 | 0.82881 (3) | 0.41666 (2) | 0.14832 (2) | 0.04191 (13) | |
S1A | 0.99433 (10) | 0.21119 (8) | 0.40978 (7) | 0.0610 (3) | 0.9 |
S1B | 1.0903 (7) | 0.2121 (5) | 0.4026 (4) | 0.061 (3) | 0.1 |
S2A | 0.74299 (11) | 0.57618 (7) | 0.03326 (7) | 0.0602 (3) | 0.9 |
S2B | 0.8396 (8) | 0.5709 (7) | 0.0687 (7) | 0.114 (6) | 0.1 |
O1 | 1.0652 (2) | 0.37418 (15) | 0.25736 (16) | 0.0586 (7) | |
O2 | 0.8821 (2) | 0.37181 (15) | 0.32921 (16) | 0.0582 (7) | |
O3 | 0.9657 (2) | 0.26105 (14) | 0.15036 (15) | 0.0517 (6) | |
O4 | 0.7790 (2) | 0.25744 (15) | 0.22302 (16) | 0.0562 (7) | |
O5 | 1.0067 (3) | 0.21484 (16) | 0.32574 (14) | 0.0641 (8) | |
O6 | 0.9838 (2) | 0.46225 (16) | 0.16653 (16) | 0.0559 (7) | |
O7 | 0.8082 (2) | 0.46791 (15) | 0.24484 (16) | 0.0581 (7) | |
O8 | 0.8666 (2) | 0.34859 (15) | 0.06551 (15) | 0.0563 (7) | |
O9 | 0.6917 (2) | 0.35589 (16) | 0.14871 (17) | 0.0595 (7) | |
O10A | 0.7249 (4) | 0.4970 (3) | 0.0649 (3) | 0.0579 (15) | 0.9 |
O10B | 0.749 (2) | 0.5152 (19) | 0.078 (3) | 0.060 (14) | 0.1 |
C10 | 0.9291 (3) | 0.2895 (2) | 0.0821 (2) | 0.0450 (8) | |
C11 | 0.9654 (3) | 0.2498 (2) | 0.0143 (2) | 0.0470 (8) | |
C12 | 1.0503 (3) | 0.1937 (2) | 0.0280 (3) | 0.0571 (10) | |
H12 | 1.085 | 0.1794 | 0.0798 | 0.068* | |
C13 | 1.0838 (5) | 0.1589 (3) | −0.0356 (3) | 0.0778 (14) | |
H13 | 1.1411 | 0.1212 | −0.0262 | 0.093* | |
C14 | 1.0337 (5) | 0.1793 (3) | −0.1117 (3) | 0.0791 (15) | |
H14 | 1.0569 | 0.1557 | −0.154 | 0.095* | |
C15 | 0.9494 (5) | 0.2343 (3) | −0.1259 (3) | 0.0743 (13) | |
H15 | 0.9153 | 0.248 | −0.1779 | 0.089* | |
C16 | 0.9146 (4) | 0.2696 (2) | −0.0639 (2) | 0.0583 (10) | |
H16 | 0.8567 | 0.3068 | −0.0742 | 0.07* | |
C20 | 0.6924 (3) | 0.2906 (2) | 0.1824 (2) | 0.0471 (8) | |
C21 | 0.5809 (3) | 0.2494 (2) | 0.1723 (2) | 0.0507 (9) | |
C22 | 0.5777 (4) | 0.1690 (3) | 0.1825 (3) | 0.0622 (11) | |
H22 | 0.6452 | 0.1409 | 0.1982 | 0.075* | |
C23 | 0.4734 (4) | 0.1304 (3) | 0.1691 (3) | 0.0803 (14) | |
H23 | 0.4716 | 0.0765 | 0.1762 | 0.096* | |
C24 | 0.3751 (5) | 0.1702 (4) | 0.1460 (3) | 0.0900 (17) | |
H24 | 0.3061 | 0.1434 | 0.1364 | 0.108* | |
C25 | 0.3754 (4) | 0.2504 (4) | 0.1365 (3) | 0.0887 (16) | |
H25 | 0.307 | 0.2777 | 0.1221 | 0.106* | |
C26 | 0.4797 (4) | 0.2905 (3) | 0.1486 (3) | 0.0719 (13) | |
H26 | 0.4808 | 0.3443 | 0.1408 | 0.086* | |
C30 | 0.8307 (3) | 0.4364 (2) | 0.3126 (2) | 0.0474 (8) | |
C31 | 0.7931 (3) | 0.4795 (2) | 0.3774 (2) | 0.0474 (8) | |
C32 | 0.8425 (4) | 0.4676 (2) | 0.4565 (2) | 0.0609 (10) | |
H32 | 0.9008 | 0.431 | 0.4711 | 0.073* | |
C33 | 0.8056 (4) | 0.5098 (3) | 0.5145 (3) | 0.0738 (13) | |
H33 | 0.8399 | 0.5022 | 0.5679 | 0.089* | |
C34 | 0.7193 (4) | 0.5623 (3) | 0.4933 (3) | 0.0754 (13) | |
H34 | 0.6944 | 0.59 | 0.5326 | 0.09* | |
C35 | 0.6683 (4) | 0.5751 (3) | 0.4151 (3) | 0.0738 (13) | |
H35 | 0.609 | 0.611 | 0.4012 | 0.089* | |
C36 | 0.7064 (4) | 0.5341 (3) | 0.3573 (3) | 0.0636 (11) | |
H36 | 0.6732 | 0.5432 | 0.304 | 0.076* | |
C40 | 1.0668 (3) | 0.4357 (2) | 0.2177 (2) | 0.0465 (8) | |
C41 | 1.1761 (3) | 0.4806 (2) | 0.2323 (2) | 0.0469 (8) | |
C42 | 1.2739 (4) | 0.4516 (3) | 0.2815 (3) | 0.0717 (13) | |
H42 | 1.2725 | 0.4028 | 0.3052 | 0.086* | |
C43 | 1.3731 (4) | 0.4941 (3) | 0.2959 (3) | 0.0926 (18) | |
H43 | 1.4389 | 0.4734 | 0.3284 | 0.111* | |
C44 | 1.3762 (4) | 0.5673 (3) | 0.2624 (3) | 0.0741 (13) | |
H44 | 1.4436 | 0.596 | 0.2724 | 0.089* | |
C45 | 1.2803 (4) | 0.5970 (3) | 0.2148 (3) | 0.0640 (11) | |
H45 | 1.2821 | 0.6463 | 0.1924 | 0.077* | |
C46 | 1.1802 (3) | 0.5549 (2) | 0.1993 (2) | 0.0580 (10) | |
H46 | 1.1149 | 0.576 | 0.1667 | 0.07* | |
C51 | 1.0613 (5) | 0.1230 (3) | 0.4488 (3) | 0.0939 (18) | |
H51A | 1.0156 | 0.0793 | 0.4255 | 0.141* | 0.9 |
H51B | 1.0694 | 0.1222 | 0.5055 | 0.141* | 0.9 |
H51C | 1.1353 | 0.1196 | 0.4368 | 0.141* | 0.9 |
H51D | 0.9926 | 0.1001 | 0.4184 | 0.141* | 0.1 |
H51E | 1.0525 | 0.134 | 0.5017 | 0.141* | 0.1 |
H51F | 1.1237 | 0.0873 | 0.4515 | 0.141* | 0.1 |
C52A | 1.0970 (6) | 0.2787 (4) | 0.4633 (4) | 0.098 (2) | 0.9 |
H52A | 1.0736 | 0.3312 | 0.4478 | 0.148* | 0.9 |
H52B | 1.1699 | 0.2686 | 0.4515 | 0.148* | 0.9 |
H52C | 1.1026 | 0.2725 | 0.5193 | 0.148* | 0.9 |
C52B | 1.038 (4) | 0.272 (2) | 0.471 (2) | 0.056 (11) | 0.1 |
H52D | 1.0603 | 0.3249 | 0.4656 | 0.084* | 0.1 |
H52E | 1.0695 | 0.2537 | 0.5241 | 0.084* | 0.1 |
H52F | 0.9565 | 0.268 | 0.4599 | 0.084* | 0.1 |
C61 | 0.8633 (5) | 0.5661 (4) | −0.0107 (4) | 0.117 (2) | |
H61A | 0.9282 | 0.5491 | 0.029 | 0.176* | 0.9 |
H61B | 0.8798 | 0.6156 | −0.0319 | 0.176* | 0.9 |
H61C | 0.8465 | 0.5281 | −0.0527 | 0.176* | 0.9 |
H61D | 0.9346 | 0.5394 | −0.0073 | 0.176* | 0.1 |
H61E | 0.8683 | 0.618 | −0.0309 | 0.176* | 0.1 |
H61F | 0.8033 | 0.5379 | −0.0453 | 0.176* | 0.1 |
C62 | 0.8034 (6) | 0.6358 (4) | 0.1155 (4) | 0.122 (2) | |
H62A | 0.7517 | 0.6393 | 0.1504 | 0.183* | 0.9 |
H62B | 0.8171 | 0.6872 | 0.0972 | 0.183* | 0.9 |
H62C | 0.8742 | 0.6133 | 0.1436 | 0.183* | 0.9 |
H62D | 0.8659 | 0.6499 | 0.1583 | 0.183* | 0.1 |
H62E | 0.7401 | 0.6188 | 0.1364 | 0.183* | 0.1 |
H62F | 0.7813 | 0.6802 | 0.0814 | 0.183* | 0.1 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0471 (2) | 0.0408 (2) | 0.0364 (2) | 0.00148 (18) | 0.00667 (18) | 0.00381 (18) |
Cu2 | 0.0447 (2) | 0.0413 (2) | 0.0385 (2) | 0.00064 (19) | 0.00698 (18) | 0.00424 (18) |
S1A | 0.0582 (7) | 0.0745 (8) | 0.0519 (6) | 0.0120 (6) | 0.0162 (5) | 0.0182 (6) |
S1B | 0.050 (6) | 0.073 (7) | 0.056 (6) | 0.008 (5) | 0.002 (5) | −0.006 (5) |
S2A | 0.0656 (7) | 0.0497 (6) | 0.0574 (7) | 0.0016 (6) | −0.0028 (6) | 0.0144 (5) |
S2B | 0.107 (13) | 0.072 (9) | 0.171 (19) | −0.004 (9) | 0.047 (13) | 0.046 (11) |
O1 | 0.0529 (15) | 0.0550 (16) | 0.0628 (17) | −0.0087 (13) | 0.0022 (13) | 0.0064 (14) |
O2 | 0.0734 (18) | 0.0533 (16) | 0.0486 (15) | 0.0152 (14) | 0.0149 (13) | −0.0028 (12) |
O3 | 0.0636 (16) | 0.0496 (14) | 0.0427 (14) | 0.0051 (13) | 0.0138 (12) | 0.0031 (12) |
O4 | 0.0490 (15) | 0.0556 (15) | 0.0614 (17) | −0.0064 (13) | 0.0068 (13) | 0.0111 (13) |
O5 | 0.089 (2) | 0.0574 (16) | 0.0424 (15) | 0.0252 (15) | 0.0083 (14) | 0.0098 (12) |
O6 | 0.0454 (14) | 0.0598 (16) | 0.0593 (16) | −0.0064 (12) | 0.0051 (12) | 0.0099 (13) |
O7 | 0.0740 (18) | 0.0528 (15) | 0.0500 (16) | 0.0129 (14) | 0.0192 (14) | 0.0010 (13) |
O8 | 0.0706 (18) | 0.0554 (16) | 0.0412 (14) | 0.0115 (14) | 0.0091 (12) | −0.0003 (12) |
O9 | 0.0527 (15) | 0.0566 (16) | 0.0664 (18) | −0.0086 (13) | 0.0079 (13) | 0.0124 (14) |
O10A | 0.057 (2) | 0.046 (2) | 0.063 (3) | −0.005 (2) | −0.0031 (19) | 0.014 (3) |
O10B | 0.08 (3) | 0.034 (19) | 0.06 (2) | −0.027 (16) | 0.00 (2) | −0.016 (17) |
C10 | 0.0445 (19) | 0.047 (2) | 0.043 (2) | −0.0052 (16) | 0.0087 (16) | −0.0015 (16) |
C11 | 0.052 (2) | 0.0420 (19) | 0.050 (2) | −0.0094 (16) | 0.0174 (17) | −0.0028 (16) |
C12 | 0.060 (2) | 0.055 (2) | 0.058 (2) | 0.0024 (19) | 0.0176 (19) | 0.0022 (19) |
C13 | 0.093 (4) | 0.061 (3) | 0.090 (4) | 0.014 (3) | 0.041 (3) | −0.002 (3) |
C14 | 0.114 (4) | 0.065 (3) | 0.070 (3) | −0.003 (3) | 0.046 (3) | −0.018 (2) |
C15 | 0.103 (4) | 0.073 (3) | 0.046 (2) | −0.008 (3) | 0.016 (2) | −0.009 (2) |
C16 | 0.070 (3) | 0.060 (2) | 0.044 (2) | 0.003 (2) | 0.0122 (19) | 0.0005 (19) |
C20 | 0.054 (2) | 0.051 (2) | 0.0373 (18) | −0.0043 (17) | 0.0123 (16) | −0.0048 (16) |
C21 | 0.050 (2) | 0.062 (2) | 0.0405 (19) | −0.0075 (18) | 0.0108 (17) | 0.0031 (17) |
C22 | 0.065 (3) | 0.062 (2) | 0.059 (3) | −0.012 (2) | 0.013 (2) | 0.006 (2) |
C23 | 0.069 (3) | 0.078 (3) | 0.091 (4) | −0.021 (3) | 0.012 (3) | 0.013 (3) |
C24 | 0.066 (3) | 0.113 (5) | 0.087 (4) | −0.037 (3) | 0.009 (3) | 0.022 (3) |
C25 | 0.050 (3) | 0.120 (5) | 0.091 (4) | −0.004 (3) | 0.005 (3) | 0.020 (3) |
C26 | 0.060 (3) | 0.082 (3) | 0.071 (3) | −0.008 (2) | 0.011 (2) | 0.014 (2) |
C30 | 0.046 (2) | 0.046 (2) | 0.050 (2) | −0.0037 (16) | 0.0127 (17) | −0.0050 (17) |
C31 | 0.046 (2) | 0.045 (2) | 0.052 (2) | −0.0038 (16) | 0.0141 (17) | −0.0051 (17) |
C32 | 0.069 (3) | 0.059 (2) | 0.054 (2) | 0.011 (2) | 0.012 (2) | −0.007 (2) |
C33 | 0.099 (4) | 0.074 (3) | 0.049 (2) | 0.009 (3) | 0.018 (2) | −0.006 (2) |
C34 | 0.092 (3) | 0.072 (3) | 0.068 (3) | 0.007 (3) | 0.029 (3) | −0.019 (2) |
C35 | 0.076 (3) | 0.074 (3) | 0.073 (3) | 0.018 (2) | 0.018 (2) | −0.013 (2) |
C36 | 0.063 (2) | 0.066 (3) | 0.061 (3) | 0.011 (2) | 0.012 (2) | −0.007 (2) |
C40 | 0.050 (2) | 0.051 (2) | 0.0390 (19) | −0.0017 (17) | 0.0104 (16) | −0.0025 (16) |
C41 | 0.0428 (19) | 0.055 (2) | 0.0426 (19) | −0.0033 (16) | 0.0087 (15) | −0.0023 (17) |
C42 | 0.059 (3) | 0.068 (3) | 0.080 (3) | −0.007 (2) | −0.002 (2) | 0.019 (2) |
C43 | 0.051 (3) | 0.100 (4) | 0.111 (4) | −0.012 (3) | −0.015 (3) | 0.040 (3) |
C44 | 0.049 (2) | 0.083 (3) | 0.084 (3) | −0.018 (2) | 0.003 (2) | 0.015 (3) |
C45 | 0.058 (2) | 0.064 (3) | 0.069 (3) | −0.011 (2) | 0.012 (2) | 0.012 (2) |
C46 | 0.051 (2) | 0.063 (2) | 0.057 (2) | −0.0020 (19) | 0.0060 (19) | 0.006 (2) |
C51 | 0.116 (4) | 0.094 (4) | 0.073 (3) | 0.030 (3) | 0.025 (3) | 0.044 (3) |
C52A | 0.103 (5) | 0.113 (5) | 0.070 (4) | −0.016 (4) | −0.001 (4) | 0.002 (3) |
C52B | 0.059 (13) | 0.058 (13) | 0.048 (13) | 0.000 (8) | 0.008 (8) | −0.006 (8) |
C61 | 0.125 (5) | 0.145 (6) | 0.096 (5) | −0.027 (5) | 0.055 (4) | 0.007 (4) |
C62 | 0.130 (5) | 0.081 (4) | 0.137 (6) | 0.001 (4) | −0.006 (4) | −0.044 (4) |
Geometric parameters (Å, º) top
Cu2—Cu1 | 2.6490 (6) | C14—C13 | 1.361 (7) |
Cu1—O1 | 1.963 (3) | C14—H14 | 0.93 |
Cu1—O2 | 1.988 (3) | C13—C12 | 1.386 (6) |
Cu1—O3 | 1.975 (3) | C13—H13 | 0.93 |
Cu1—O4 | 1.966 (3) | C12—H12 | 0.93 |
Cu1—O5 | 2.135 (2) | O7—C30 | 1.260 (4) |
Cu2—O6 | 1.979 (3) | O2—C30 | 1.266 (4) |
Cu2—O7 | 1.946 (3) | C30—C31 | 1.493 (5) |
Cu2—O8 | 1.973 (3) | C31—C32 | 1.376 (5) |
Cu2—O9 | 1.950 (3) | C31—C36 | 1.384 (5) |
Cu2—O10A | 2.169 (4) | C36—C35 | 1.379 (6) |
Cu2—O10B | 2.17 (2) | C36—H36 | 0.93 |
C61—S2A | 1.788 (6) | C35—C34 | 1.369 (7) |
C61—H61A | 0.96 | C35—H35 | 0.93 |
C61—H61B | 0.96 | C34—C33 | 1.358 (6) |
C61—H61C | 0.96 | C34—H34 | 0.93 |
C61—H61D | 0.96 | C33—C32 | 1.386 (6) |
C61—H61E | 0.96 | C33—H33 | 0.93 |
C61—H61F | 0.95 | C32—H32 | 0.93 |
C62—S2A | 1.764 (6) | O6—C40 | 1.259 (4) |
C62—H62A | 0.96 | O1—C40 | 1.257 (4) |
C62—H62B | 0.96 | C40—C41 | 1.494 (5) |
C62—H62C | 0.96 | C41—C42 | 1.378 (5) |
C62—H62D | 0.96 | C41—C46 | 1.395 (5) |
C62—H62E | 0.96 | C46—C45 | 1.376 (5) |
C62—H62F | 0.96 | C46—H46 | 0.93 |
S2B—O10B | 1.49 (2) | C45—C44 | 1.355 (6) |
O10A—S2A | 1.494 (4) | C45—H45 | 0.93 |
O9—C20 | 1.257 (4) | C44—C43 | 1.381 (6) |
O4—C20 | 1.253 (4) | C44—H44 | 0.93 |
C20—C21 | 1.490 (5) | C43—C42 | 1.371 (6) |
C21—C26 | 1.385 (6) | C43—H43 | 0.93 |
C21—C22 | 1.385 (6) | C42—H42 | 0.93 |
C26—C25 | 1.403 (6) | O5—S1B | 1.474 (5) |
C26—H26 | 0.93 | O5—S1A | 1.492 (3) |
C25—C24 | 1.379 (8) | C51—S1A | 1.769 (4) |
C25—H25 | 0.93 | C51—H51A | 0.96 |
C24—C23 | 1.344 (7) | C51—H51B | 0.96 |
C24—H24 | 0.93 | C51—H51C | 0.96 |
C23—C22 | 1.390 (6) | C51—H51D | 0.96 |
C23—H23 | 0.93 | C51—H51E | 0.96 |
C22—H22 | 0.93 | C51—H51F | 0.96 |
O3—C10 | 1.259 (4) | S1A—C52A | 1.787 (5) |
O8—C10 | 1.252 (4) | C52A—H52A | 0.96 |
C10—C11 | 1.499 (5) | C52A—H52B | 0.96 |
C11—C12 | 1.382 (5) | C52A—H52C | 0.96 |
C11—C16 | 1.392 (5) | S1B—C52B | 1.773 (6) |
C16—C15 | 1.373 (6) | C52B—H52D | 0.96 |
C16—H16 | 0.93 | C52B—H52E | 0.96 |
C15—C14 | 1.363 (7) | C52B—H52F | 0.96 |
C15—H15 | 0.93 | | |
| | | |
S2A—C61—H61A | 109.5 | C15—C16—C11 | 120.3 (4) |
S2A—C61—H61B | 109.5 | C15—C16—H16 | 119.9 |
H61A—C61—H61B | 109.5 | C11—C16—H16 | 119.9 |
S2A—C61—H61C | 109.5 | C14—C15—C16 | 120.6 (4) |
H61A—C61—H61C | 109.5 | C14—C15—H15 | 119.7 |
H61B—C61—H61C | 109.5 | C16—C15—H15 | 119.7 |
H61D—C61—H61E | 109.4 | C13—C14—C15 | 119.9 (4) |
H61D—C61—H61F | 109.6 | C13—C14—H14 | 120.1 |
H61E—C61—H61F | 109.8 | C15—C14—H14 | 120.1 |
S2A—C62—H62A | 109.5 | C14—C13—C12 | 120.7 (5) |
S2A—C62—H62B | 109.5 | C14—C13—H13 | 119.7 |
H62A—C62—H62B | 109.5 | C12—C13—H13 | 119.7 |
S2A—C62—H62C | 109.5 | C11—C12—C13 | 119.9 (4) |
H62A—C62—H62C | 109.5 | C11—C12—H12 | 120.1 |
H62B—C62—H62C | 109.5 | C13—C12—H12 | 120.1 |
H62D—C62—H62E | 109.7 | C30—O7—Cu2 | 124.1 (2) |
H62D—C62—H62F | 109.5 | C30—O2—Cu1 | 122.3 (2) |
H62E—C62—H62F | 109.7 | O7—C30—O2 | 125.1 (3) |
S2B—O10B—Cu2 | 108.2 (15) | O7—C30—C31 | 116.6 (3) |
S2A—O10A—Cu2 | 134.9 (3) | O2—C30—C31 | 118.4 (3) |
O10A—S2A—C62 | 107.2 (3) | C32—C31—C36 | 118.8 (4) |
O10A—S2A—C61 | 105.5 (3) | C32—C31—C30 | 122.3 (3) |
C62—S2A—C61 | 99.8 (3) | C36—C31—C30 | 118.9 (3) |
O7—Cu2—O9 | 88.00 (12) | C35—C36—C31 | 121.0 (4) |
O7—Cu2—O8 | 168.34 (11) | C35—C36—H36 | 119.5 |
O9—Cu2—O8 | 91.29 (12) | C31—C36—H36 | 119.5 |
O7—Cu2—O6 | 89.12 (12) | C34—C35—C36 | 119.0 (4) |
O9—Cu2—O6 | 167.45 (11) | C34—C35—H35 | 120.5 |
O8—Cu2—O6 | 89.07 (12) | C36—C35—H35 | 120.5 |
O7—Cu2—O10A | 96.77 (19) | C33—C34—C35 | 121.1 (4) |
O9—Cu2—O10A | 88.69 (16) | C33—C34—H34 | 119.4 |
O8—Cu2—O10A | 94.85 (19) | C35—C34—H34 | 119.4 |
O6—Cu2—O10A | 103.79 (15) | C34—C33—C32 | 119.9 (4) |
O7—Cu2—O10B | 90.3 (17) | C34—C33—H33 | 120 |
O9—Cu2—O10B | 98.3 (7) | C32—C33—H33 | 120 |
O8—Cu2—O10B | 101.4 (17) | C31—C32—C33 | 120.2 (4) |
O6—Cu2—O10B | 93.9 (7) | C31—C32—H32 | 119.9 |
O7—Cu2—Cu1 | 84.07 (8) | C33—C32—H32 | 119.9 |
O9—Cu2—Cu1 | 83.62 (8) | C40—O6—Cu2 | 122.7 (2) |
O8—Cu2—Cu1 | 84.28 (8) | C40—O1—Cu1 | 123.9 (2) |
O6—Cu2—Cu1 | 83.94 (8) | O1—C40—O6 | 125.1 (3) |
O10A—Cu2—Cu1 | 172.23 (13) | O1—C40—C41 | 117.3 (3) |
O10B—Cu2—Cu1 | 173.9 (16) | O6—C40—C41 | 117.5 (3) |
O1—Cu1—O4 | 167.54 (11) | C42—C41—C46 | 118.3 (4) |
O1—Cu1—O3 | 88.69 (11) | C42—C41—C40 | 121.0 (4) |
O4—Cu1—O3 | 90.92 (12) | C46—C41—C40 | 120.6 (3) |
O1—Cu1—O2 | 88.65 (12) | C45—C46—C41 | 120.3 (4) |
O4—Cu1—O2 | 89.04 (12) | C45—C46—H46 | 119.8 |
O3—Cu1—O2 | 167.37 (11) | C41—C46—H46 | 119.8 |
O1—Cu1—O5 | 98.61 (12) | C44—C45—C46 | 120.7 (4) |
O4—Cu1—O5 | 93.81 (12) | C44—C45—H45 | 119.6 |
O3—Cu1—O5 | 96.09 (10) | C46—C45—H45 | 119.6 |
O2—Cu1—O5 | 96.52 (10) | C45—C44—C43 | 119.6 (4) |
O1—Cu1—Cu2 | 83.76 (8) | C45—C44—H44 | 120.2 |
O4—Cu1—Cu2 | 83.83 (8) | C43—C44—H44 | 120.2 |
O3—Cu1—Cu2 | 83.58 (7) | C42—C43—C44 | 120.5 (4) |
O2—Cu1—Cu2 | 83.85 (8) | C42—C43—H43 | 119.8 |
O5—Cu1—Cu2 | 177.61 (9) | C44—C43—H43 | 119.8 |
C20—O9—Cu2 | 123.8 (3) | C43—C42—C41 | 120.6 (4) |
C20—O4—Cu1 | 122.8 (2) | C43—C42—H42 | 119.7 |
O4—C20—O9 | 125.3 (3) | C41—C42—H42 | 119.7 |
O4—C20—C21 | 117.7 (3) | S1B—O5—Cu1 | 134.5 (3) |
O9—C20—C21 | 117.0 (3) | S1A—O5—Cu1 | 121.62 (16) |
C26—C21—C22 | 119.4 (4) | S1A—C51—H51A | 109.5 |
C26—C21—C20 | 120.3 (4) | S1A—C51—H51B | 109.5 |
C22—C21—C20 | 120.2 (4) | H51A—C51—H51B | 109.5 |
C21—C26—C25 | 119.6 (5) | S1A—C51—H51C | 109.5 |
C21—C26—H26 | 120.2 | H51A—C51—H51C | 109.5 |
C25—C26—H26 | 120.2 | H51B—C51—H51C | 109.5 |
C24—C25—C26 | 119.5 (5) | H51D—C51—H51E | 109.5 |
C24—C25—H25 | 120.2 | H51D—C51—H51F | 109.7 |
C26—C25—H25 | 120.2 | H51E—C51—H51F | 109.3 |
C23—C24—C25 | 120.8 (5) | O5—S1A—C51 | 105.6 (2) |
C23—C24—H24 | 119.6 | O5—S1A—C52A | 105.5 (3) |
C25—C24—H24 | 119.6 | C51—S1A—C52A | 98.6 (3) |
C24—C23—C22 | 120.7 (5) | S1A—C52A—H52A | 109.5 |
C24—C23—H23 | 119.7 | S1A—C52A—H52B | 109.5 |
C22—C23—H23 | 119.7 | H52A—C52A—H52B | 109.5 |
C21—C22—C23 | 119.9 (4) | S1A—C52A—H52C | 109.5 |
C21—C22—H22 | 120 | H52A—C52A—H52C | 109.5 |
C23—C22—H22 | 120 | H52B—C52A—H52C | 109.5 |
C10—O3—Cu1 | 123.1 (2) | O5—S1B—C52B | 107.9 (17) |
C10—O8—Cu2 | 122.3 (2) | S1B—C52B—H52D | 109.5 |
O8—C10—O3 | 126.1 (3) | S1B—C52B—H52E | 109.5 |
O8—C10—C11 | 116.9 (3) | H52D—C52B—H52E | 109.5 |
O3—C10—C11 | 117.0 (3) | S1B—C52B—H52F | 109.5 |
C12—C11—C16 | 118.7 (4) | H52D—C52B—H52F | 109.5 |
C12—C11—C10 | 121.0 (4) | H52E—C52B—H52F | 109.5 |
C16—C11—C10 | 120.4 (3) | | |
| | | |
Cu2—O10A—S2A—C62 | −48.4 (6) | C10—C11—C16—C15 | 178.7 (4) |
Cu2—O10A—S2A—C61 | 57.3 (6) | C11—C16—C15—C14 | 0.3 (7) |
S2A—O10A—Cu2—O7 | 80.2 (6) | C16—C15—C14—C13 | 0.1 (8) |
S2A—O10A—Cu2—O9 | 168.0 (6) | C15—C14—C13—C12 | −0.2 (8) |
S2A—O10A—Cu2—O8 | −100.8 (6) | C16—C11—C12—C13 | 0.5 (6) |
S2A—O10A—Cu2—O6 | −10.6 (6) | C10—C11—C12—C13 | −178.8 (4) |
S2B—O10B—Cu2—O7 | 92 (3) | C14—C13—C12—C11 | −0.1 (7) |
S2B—O10B—Cu2—O9 | −180 (3) | O9—Cu2—O7—C30 | 75.6 (3) |
S2B—O10B—Cu2—O8 | −86 (3) | O8—Cu2—O7—C30 | −11.1 (8) |
S2B—O10B—Cu2—O6 | 3 (3) | O6—Cu2—O7—C30 | −92.2 (3) |
O7—Cu2—Cu1—O1 | −84.82 (12) | O10A—Cu2—O7—C30 | 164.1 (3) |
O9—Cu2—Cu1—O1 | −173.46 (12) | O10B—Cu2—O7—C30 | 174.0 (7) |
O8—Cu2—Cu1—O1 | 94.59 (12) | Cu1—Cu2—O7—C30 | −8.2 (3) |
O6—Cu2—Cu1—O1 | 4.92 (11) | O1—Cu1—O2—C30 | 81.2 (3) |
O7—Cu2—Cu1—O4 | 94.18 (12) | O4—Cu1—O2—C30 | −86.6 (3) |
O9—Cu2—Cu1—O4 | 5.53 (12) | O3—Cu1—O2—C30 | 3.3 (7) |
O8—Cu2—Cu1—O4 | −86.41 (12) | O5—Cu1—O2—C30 | 179.7 (3) |
O6—Cu2—Cu1—O4 | −176.08 (12) | Cu2—Cu1—O2—C30 | −2.7 (3) |
O7—Cu2—Cu1—O3 | −174.20 (11) | Cu2—O7—C30—O2 | 9.0 (5) |
O9—Cu2—Cu1—O3 | 97.16 (12) | Cu2—O7—C30—C31 | −170.9 (2) |
O8—Cu2—Cu1—O3 | 5.22 (11) | Cu1—O2—C30—O7 | −2.6 (5) |
O6—Cu2—Cu1—O3 | −84.45 (11) | Cu1—O2—C30—C31 | 177.3 (2) |
O7—Cu2—Cu1—O2 | 4.48 (12) | O7—C30—C31—C32 | −157.8 (4) |
O9—Cu2—Cu1—O2 | −84.16 (12) | O2—C30—C31—C32 | 22.3 (5) |
O8—Cu2—Cu1—O2 | −176.10 (12) | O7—C30—C31—C36 | 21.5 (5) |
O6—Cu2—Cu1—O2 | 94.23 (12) | O2—C30—C31—C36 | −158.5 (4) |
O7—Cu2—O9—C20 | −90.8 (3) | C32—C31—C36—C35 | −1.0 (6) |
O8—Cu2—O9—C20 | 77.6 (3) | C30—C31—C36—C35 | 179.7 (4) |
O6—Cu2—O9—C20 | −13.9 (7) | C31—C36—C35—C34 | 1.3 (7) |
O10A—Cu2—O9—C20 | 172.4 (3) | C36—C35—C34—C33 | −0.4 (8) |
O10B—Cu2—O9—C20 | 179.3 (17) | C35—C34—C33—C32 | −0.8 (8) |
Cu1—Cu2—O9—C20 | −6.5 (3) | C36—C31—C32—C33 | −0.1 (6) |
O1—Cu1—O4—C20 | −2.2 (7) | C30—C31—C32—C33 | 179.1 (4) |
O3—Cu1—O4—C20 | −90.3 (3) | C34—C33—C32—C31 | 1.0 (7) |
O2—Cu1—O4—C20 | 77.1 (3) | O7—Cu2—O6—C40 | 76.5 (3) |
O5—Cu1—O4—C20 | 173.6 (3) | O9—Cu2—O6—C40 | −0.2 (7) |
Cu2—Cu1—O4—C20 | −6.8 (3) | O8—Cu2—O6—C40 | −92.0 (3) |
Cu1—O4—C20—O9 | 4.3 (5) | O10A—Cu2—O6—C40 | 173.3 (3) |
Cu1—O4—C20—C21 | −176.3 (2) | O10B—Cu2—O6—C40 | 166.7 (17) |
Cu2—O9—C20—O4 | 3.5 (5) | Cu1—Cu2—O6—C40 | −7.6 (3) |
Cu2—O9—C20—C21 | −175.9 (2) | O4—Cu1—O1—C40 | −8.9 (7) |
O4—C20—C21—C26 | 161.5 (4) | O3—Cu1—O1—C40 | 79.4 (3) |
O9—C20—C21—C26 | −19.0 (5) | O2—Cu1—O1—C40 | −88.2 (3) |
O4—C20—C21—C22 | −21.9 (5) | O5—Cu1—O1—C40 | 175.4 (3) |
O9—C20—C21—C22 | 157.6 (4) | Cu2—Cu1—O1—C40 | −4.3 (3) |
C22—C21—C26—C25 | 1.0 (7) | Cu1—O1—C40—O6 | −0.2 (5) |
C20—C21—C26—C25 | 177.6 (4) | Cu1—O1—C40—C41 | −179.9 (2) |
C21—C26—C25—C24 | −1.9 (8) | Cu2—O6—C40—O1 | 7.2 (5) |
C26—C25—C24—C23 | 2.0 (9) | Cu2—O6—C40—C41 | −173.2 (2) |
C25—C24—C23—C22 | −1.2 (9) | O1—C40—C41—C42 | 6.0 (6) |
C26—C21—C22—C23 | −0.2 (7) | O6—C40—C41—C42 | −173.6 (4) |
C20—C21—C22—C23 | −176.8 (4) | O1—C40—C41—C46 | −170.7 (4) |
C24—C23—C22—C21 | 0.2 (8) | O6—C40—C41—C46 | 9.6 (5) |
O1—Cu1—O3—C10 | −88.3 (3) | C42—C41—C46—C45 | 1.2 (6) |
O4—Cu1—O3—C10 | 79.3 (3) | C40—C41—C46—C45 | 178.0 (4) |
O2—Cu1—O3—C10 | −10.4 (7) | C41—C46—C45—C44 | −0.3 (7) |
O5—Cu1—O3—C10 | 173.2 (3) | C46—C45—C44—C43 | −0.3 (8) |
Cu2—Cu1—O3—C10 | −4.4 (3) | C45—C44—C43—C42 | −0.2 (9) |
O7—Cu2—O8—C10 | −5.2 (7) | C44—C43—C42—C41 | 1.2 (9) |
O9—Cu2—O8—C10 | −91.5 (3) | C46—C41—C42—C43 | −1.7 (7) |
O6—Cu2—O8—C10 | 75.9 (3) | C40—C41—C42—C43 | −178.5 (5) |
O10A—Cu2—O8—C10 | 179.7 (3) | O1—Cu1—O5—S1B | 39.1 (6) |
O10B—Cu2—O8—C10 | 169.7 (7) | O4—Cu1—O5—S1B | −140.0 (6) |
Cu1—Cu2—O8—C10 | −8.1 (3) | O3—Cu1—O5—S1B | 128.7 (6) |
Cu2—O8—C10—O3 | 7.7 (5) | O2—Cu1—O5—S1B | −50.5 (6) |
Cu2—O8—C10—C11 | −171.1 (2) | O1—Cu1—O5—S1A | 98.3 (2) |
Cu1—O3—C10—O8 | −0.4 (5) | O4—Cu1—O5—S1A | −80.8 (2) |
Cu1—O3—C10—C11 | 178.4 (2) | O3—Cu1—O5—S1A | −172.1 (2) |
O8—C10—C11—C12 | 167.9 (3) | O2—Cu1—O5—S1A | 8.7 (2) |
O3—C10—C11—C12 | −11.0 (5) | Cu1—O5—S1A—C51 | 175.9 (3) |
O8—C10—C11—C16 | −11.4 (5) | Cu1—O5—S1A—C52A | −80.3 (3) |
O3—C10—C11—C16 | 169.7 (3) | Cu1—O5—S1B—C52B | 56.1 (18) |
C12—C11—C16—C15 | −0.6 (6) | | |
Comparative geometric parameters (Å) for polymorph II and polymorph I topDistance | Polymorph II | Polymorph I |
Cu1—Cu2 | 2.6490 (6) | 2.627 (2) |
Cu1—O1 | 1.963 (3) | 1.96 (1) |
Cu1—O2 | 1.988 (3) | 1.93 (1) |
Cu1—O3 | 1.975 (3) | 1.97 (1) |
Cu1—O4 | 1.966 (3) | 1.99 (1) |
Cu1—O5 | 2.135 (2) | 2.16 (1) |
Cu2—O6 | 1.979 (3) | 1.95 (1) |
Cu2—O7 | 1.946 (3) | 1.95 (1) |
Cu2—O8 | 1.973 (3) | 2.00 (1) |
Cu2—O9 | 1.950 (3) | 1.95 (1) |
Cu2—O10A | 2.169 (4) | 2.17 (1) |
Cu2—O10B | 2.17 (2) | |
Hydrogen-bonding geometry (Å, °) topD—H···A | D—H | H···A | D···A | D—H···A |
C51—H51B···O9i | 0.96 | 2.60 | 3.471 (6) | 151 |
C52A—H52C···C21i | 0.96 | 2.74 | 3.687 (8) | 171 |
C62—H62D···C22ii | 0.96 | 2.70 | 3.505 (8) | 142 |
C35—H35···C12ii | 0.93 | 2.87 | 3.627 (6) | 140 |
C62—H62B···C14iii | 0.96 | 2.88 | 3.726 (8) | 148 |
C61—H61C···C46iii | 0.96 | 2.85 | 3.791 (8) | 165 |
Symmetry codes:(i) 1/2 + x, 1/2 – y, 1/2 + z; (ii) 1 1/2 – x, 1/2 + y, 1/2 –
z; (iii) 2 - x, 1 – y, – z. |