In the complex, bis[μ-N,N′-bis(pyridin-2-ylmethyl)pyrazine-2,3-dicarboxamide]bis[sulfatocopper(II)] hexahydrate, [Cu2(C18H16N6O2)2(SO4)2]·6H2O, the pyrazine ligand coordinates in a tridentate–monodentate manner with the Cu atoms having N3O2 chromophores. A neutral centrosymmetric binuclear macrocyclic structure is formed, with the Cu atoms having almost perfect square-pyramidal geometry.
Supporting information
CCDC reference: 234800
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.029
- wR factor = 0.060
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
| Author Response: ...With the Stoe Image Plate diffraction System Mark I it is
only possible to access a maximum of ca. 93% of the Ewald sphere
in the triclinic system, if maximum atomic resolution, 0.81 \%A,
is to be obtained. Here Theta max. was 25.90\%. The result of this is that
the reported bond distances and angles will not be as precise as they should
be if 100% of the data had been measured. However, the overall structure, which
is important here, is correct.
|
Alert level C
CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that
calculated from the cell parameter s.u.'s by > 2
Calculated cell volume su = 19.74
Cell volume su given = 17.00
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.90
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 3966
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 4267
Completeness (_total/calc) 92.95%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.90
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: EXPOSE (Stoe & Cie, 2000); cell refinement: CELL (Stoe & Cie, 2000); data reduction: INTEGRATE (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Crystal data top
[Cu2(C18H16N6O2)2(SO4)2]·6H2O | Z = 1 |
Mr = 1124.03 | F(000) = 578 |
Triclinic, P1 | Dx = 1.700 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9507 (8) Å | Cell parameters from 5864 reflections |
b = 10.0094 (9) Å | θ = 2.3–25.9° |
c = 13.9732 (12) Å | µ = 1.16 mm−1 |
α = 90.953 (10)° | T = 153 K |
β = 100.442 (10)° | Block, blue_green |
γ = 116.190 (9)° | 0.20 × 0.20 × 0.08 mm |
V = 1098.10 (17) Å3 | |
Data collection top
Stoe Image Plate Diffraction System diffractometer | 3966 independent reflections |
Radiation source: fine-focus sealed tube | 2687 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 0.81 pixels mm-1 | θmax = 25.9°, θmin = 2.3° |
φ oscillation scans | h = −10→10 |
Absorption correction: empirical (using intensity measurements) refined from ΔF (DELABS in PLATON; Spek, 2003) | k = −12→12 |
Tmin = 0.718, Tmax = 0.920 | l = −17→16 |
8639 measured reflections | |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = [exp{2(sinθ/λ)2}]/[σ2(Fo2) + (0.0241P)2] where P = (Fo2 + 2Fc2)/3 |
3966 reflections | (Δ/σ)max < 0.001 |
340 parameters | Δρmax = 0.35 e Å−3 |
1 restraint | Δρmin = −0.35 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 | 0.42527 (5) | 0.21574 (4) | 0.36624 (2) | 0.01374 (10) | |
S1 | 0.14055 (9) | −0.02249 (8) | 0.21680 (4) | 0.01411 (16) | |
O1 | 0.5231 (3) | 0.3292 (2) | 0.65703 (12) | 0.0191 (4) | |
O2 | 0.4185 (3) | 0.5739 (2) | 0.70690 (12) | 0.0171 (4) | |
O11 | 0.2735 (3) | 0.1385 (2) | 0.23859 (12) | 0.0178 (4) | |
O12 | 0.1102 (3) | −0.0827 (2) | 0.31034 (12) | 0.0194 (4) | |
O13 | 0.2070 (3) | −0.1056 (2) | 0.16365 (13) | 0.0239 (5) | |
O14 | −0.0143 (3) | −0.0289 (2) | 0.15671 (13) | 0.0241 (5) | |
N1 | 0.1277 (3) | 0.4319 (3) | 0.51528 (15) | 0.0156 (5) | |
N2 | 0.2880 (3) | 0.3077 (2) | 0.41816 (14) | 0.0131 (5) | |
N3 | 0.5302 (3) | 0.2497 (3) | 0.50217 (14) | 0.0144 (5) | |
N4 | 0.5889 (3) | 0.1316 (3) | 0.35846 (15) | 0.0159 (5) | |
N5 | 0.1980 (3) | 0.3583 (3) | 0.72759 (14) | 0.0160 (5) | |
H5N | 0.1168 | 0.2706 | 0.6995 | 0.019* | |
N6 | 0.3129 (3) | 0.3316 (3) | 0.99017 (15) | 0.0231 (6) | |
H6N | 0.2415 | 0.3583 | 1.0104 | 0.028* | |
C1 | 0.2510 (3) | 0.4012 (3) | 0.56459 (17) | 0.0122 (6) | |
C2 | 0.3326 (3) | 0.3389 (3) | 0.51674 (17) | 0.0116 (5) | |
C3 | 0.1689 (4) | 0.3399 (3) | 0.36865 (17) | 0.0152 (6) | |
H3 | 0.1381 | 0.3206 | 0.2993 | 0.018* | |
C4 | 0.0889 (4) | 0.4022 (3) | 0.41872 (18) | 0.0171 (6) | |
H4 | 0.0035 | 0.4241 | 0.3822 | 0.020* | |
C5 | 0.4748 (4) | 0.3044 (3) | 0.56645 (17) | 0.0124 (6) | |
C6 | 0.6617 (4) | 0.2017 (3) | 0.53427 (17) | 0.0143 (6) | |
H6A | 0.6266 | 0.1276 | 0.5820 | 0.017* | |
H6B | 0.7699 | 0.2886 | 0.5661 | 0.017* | |
C7 | 0.6848 (4) | 0.1324 (3) | 0.44483 (17) | 0.0139 (6) | |
C8 | 0.8013 (4) | 0.0742 (3) | 0.45071 (19) | 0.0184 (6) | |
H8 | 0.8630 | 0.0696 | 0.5125 | 0.022* | |
C9 | 0.8255 (4) | 0.0234 (3) | 0.3651 (2) | 0.0224 (7) | |
H9 | 0.9065 | −0.0143 | 0.3673 | 0.027* | |
C10 | 0.7310 (4) | 0.0276 (3) | 0.2760 (2) | 0.0224 (7) | |
H10 | 0.7480 | −0.0050 | 0.2165 | 0.027* | |
C11 | 0.6121 (4) | 0.0798 (3) | 0.27539 (18) | 0.0201 (6) | |
H11 | 0.5442 | 0.0793 | 0.2145 | 0.024* | |
C12 | 0.2989 (4) | 0.4509 (3) | 0.67396 (17) | 0.0117 (6) | |
C13 | 0.2178 (4) | 0.3978 (3) | 0.83183 (17) | 0.0196 (7) | |
H13A | 0.1041 | 0.3539 | 0.8486 | 0.023* | |
H13B | 0.2675 | 0.5080 | 0.8451 | 0.023* | |
C14 | 0.3294 (4) | 0.3440 (3) | 0.89638 (18) | 0.0179 (6) | |
C15 | 0.4462 (4) | 0.3070 (3) | 0.86556 (19) | 0.0217 (7) | |
H15 | 0.4632 | 0.3183 | 0.8004 | 0.026* | |
C16 | 0.5387 (4) | 0.2532 (4) | 0.9305 (2) | 0.0282 (7) | |
H16 | 0.6183 | 0.2267 | 0.9097 | 0.034* | |
C17 | 0.5146 (5) | 0.2385 (4) | 1.0253 (2) | 0.0315 (8) | |
H17 | 0.5755 | 0.2002 | 1.0699 | 0.038* | |
C18 | 0.4011 (5) | 0.2801 (4) | 1.0540 (2) | 0.0305 (8) | |
H18 | 0.3848 | 0.2724 | 1.1193 | 0.037* | |
O1W | 0.1711 (3) | 0.6140 (3) | 0.21957 (17) | 0.0302 (5) | |
H19 | 0.263 (6) | 0.637 (4) | 0.261 (3) | 0.046 (11)* | |
H20 | 0.184 (6) | 0.695 (6) | 0.201 (3) | 0.077 (17)* | |
O2W | 0.1049 (4) | 0.4056 (4) | 0.0646 (2) | 0.0532 (8) | |
H21 | 0.123 (6) | 0.479 (6) | 0.110 (3) | 0.076 (15)* | |
H22 | 0.009 (4) | 0.326 (4) | 0.067 (4) | 0.10 (2)* | |
O3W | 0.8374 (3) | 0.1282 (3) | 0.04265 (18) | 0.0332 (6) | |
H23 | 0.827 (5) | 0.114 (4) | −0.018 (3) | 0.042 (11)* | |
H24 | 0.885 (5) | 0.082 (5) | 0.071 (3) | 0.052 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0141 (2) | 0.0154 (2) | 0.01247 (16) | 0.00731 (18) | 0.00301 (13) | 0.00107 (13) |
S1 | 0.0129 (4) | 0.0141 (4) | 0.0132 (3) | 0.0046 (4) | 0.0017 (3) | 0.0000 (3) |
O1 | 0.0202 (12) | 0.0283 (12) | 0.0127 (9) | 0.0154 (11) | 0.0012 (8) | 0.0000 (8) |
O2 | 0.0177 (13) | 0.0129 (11) | 0.0151 (9) | 0.0020 (11) | 0.0036 (8) | 0.0010 (8) |
O11 | 0.0192 (12) | 0.0143 (11) | 0.0142 (8) | 0.0032 (11) | 0.0020 (8) | 0.0004 (7) |
O12 | 0.0181 (12) | 0.0208 (12) | 0.0172 (9) | 0.0062 (11) | 0.0055 (8) | 0.0047 (8) |
O13 | 0.0280 (14) | 0.0233 (12) | 0.0246 (10) | 0.0150 (12) | 0.0069 (9) | −0.0022 (8) |
O14 | 0.0159 (13) | 0.0272 (13) | 0.0249 (10) | 0.0092 (12) | −0.0045 (8) | −0.0003 (8) |
N1 | 0.0154 (14) | 0.0162 (14) | 0.0170 (11) | 0.0083 (13) | 0.0043 (10) | 0.0023 (9) |
N2 | 0.0113 (14) | 0.0109 (12) | 0.0143 (10) | 0.0026 (12) | 0.0024 (9) | 0.0022 (9) |
N3 | 0.0124 (14) | 0.0154 (13) | 0.0171 (10) | 0.0078 (12) | 0.0028 (9) | 0.0027 (9) |
N4 | 0.0134 (14) | 0.0126 (13) | 0.0189 (11) | 0.0030 (12) | 0.0046 (9) | 0.0033 (9) |
N5 | 0.0145 (14) | 0.0144 (13) | 0.0126 (10) | 0.0015 (12) | 0.0015 (9) | −0.0008 (9) |
N6 | 0.0221 (16) | 0.0243 (15) | 0.0154 (11) | 0.0033 (14) | 0.0061 (10) | −0.0005 (10) |
C1 | 0.0082 (16) | 0.0095 (15) | 0.0148 (12) | 0.0004 (14) | 0.0024 (10) | 0.0014 (10) |
C2 | 0.0090 (16) | 0.0083 (14) | 0.0139 (11) | 0.0008 (14) | 0.0021 (10) | 0.0018 (10) |
C3 | 0.0142 (17) | 0.0160 (16) | 0.0122 (12) | 0.0047 (15) | 0.0013 (11) | 0.0018 (10) |
C4 | 0.0129 (17) | 0.0177 (16) | 0.0204 (13) | 0.0081 (15) | 0.0000 (11) | 0.0028 (11) |
C5 | 0.0113 (16) | 0.0074 (14) | 0.0154 (12) | 0.0011 (14) | 0.0038 (11) | 0.0040 (10) |
C6 | 0.0149 (16) | 0.0166 (15) | 0.0142 (12) | 0.0095 (15) | 0.0029 (10) | 0.0047 (10) |
C7 | 0.0129 (17) | 0.0098 (15) | 0.0177 (12) | 0.0026 (14) | 0.0063 (11) | 0.0033 (10) |
C8 | 0.0148 (17) | 0.0145 (16) | 0.0248 (14) | 0.0057 (15) | 0.0040 (12) | 0.0038 (11) |
C9 | 0.0168 (18) | 0.0156 (17) | 0.0354 (16) | 0.0064 (16) | 0.0095 (13) | 0.0012 (12) |
C10 | 0.0234 (19) | 0.0209 (17) | 0.0241 (14) | 0.0092 (16) | 0.0102 (13) | −0.0013 (12) |
C11 | 0.0226 (19) | 0.0219 (17) | 0.0149 (12) | 0.0081 (16) | 0.0072 (12) | 0.0015 (11) |
C12 | 0.0126 (17) | 0.0097 (16) | 0.0155 (12) | 0.0070 (15) | 0.0041 (11) | 0.0027 (11) |
C13 | 0.0202 (18) | 0.0269 (18) | 0.0134 (12) | 0.0118 (16) | 0.0051 (11) | 0.0005 (11) |
C14 | 0.0178 (17) | 0.0130 (16) | 0.0120 (12) | −0.0028 (15) | 0.0034 (11) | −0.0007 (10) |
C15 | 0.0224 (19) | 0.0242 (18) | 0.0169 (13) | 0.0082 (17) | 0.0058 (12) | 0.0053 (12) |
C16 | 0.028 (2) | 0.027 (2) | 0.0276 (15) | 0.0115 (18) | 0.0052 (14) | 0.0039 (13) |
C17 | 0.033 (2) | 0.0259 (19) | 0.0259 (15) | 0.0081 (19) | −0.0023 (14) | 0.0069 (13) |
C18 | 0.036 (2) | 0.030 (2) | 0.0146 (13) | 0.0051 (19) | 0.0051 (13) | 0.0063 (12) |
O1W | 0.0244 (16) | 0.0289 (15) | 0.0343 (12) | 0.0134 (14) | −0.0042 (11) | −0.0016 (11) |
O2W | 0.043 (2) | 0.0400 (19) | 0.0669 (18) | 0.0058 (18) | 0.0258 (15) | −0.0148 (14) |
O3W | 0.0441 (17) | 0.0359 (15) | 0.0235 (12) | 0.0228 (14) | 0.0041 (11) | 0.0028 (10) |
Geometric parameters (Å, º) top
Cu1—N3 | 1.912 (2) | C3—H3 | 0.9500 |
Cu1—O11 | 1.9426 (18) | C4—H4 | 0.9500 |
Cu1—N4 | 2.002 (2) | C6—C7 | 1.509 (3) |
Cu1—N2 | 2.045 (2) | C6—H6A | 0.9900 |
Cu1—O2i | 2.3292 (19) | C6—H6B | 0.9900 |
S1—O14 | 1.459 (2) | C7—C8 | 1.393 (4) |
S1—O12 | 1.4680 (18) | C8—C9 | 1.381 (4) |
S1—O13 | 1.4747 (18) | C8—H8 | 0.9500 |
S1—O11 | 1.505 (2) | C9—C10 | 1.385 (4) |
O1—C5 | 1.244 (3) | C9—H9 | 0.9500 |
O2—C12 | 1.230 (3) | C10—C11 | 1.376 (4) |
O2—Cu1i | 2.3292 (19) | C10—H10 | 0.9500 |
N1—C4 | 1.325 (3) | C11—H11 | 0.9500 |
N1—C1 | 1.348 (3) | C13—C14 | 1.505 (4) |
N2—C3 | 1.328 (3) | C13—H13A | 0.9900 |
N2—C2 | 1.353 (3) | C13—H13B | 0.9900 |
N3—C5 | 1.318 (3) | C14—C15 | 1.384 (4) |
N3—C6 | 1.460 (3) | C15—C16 | 1.391 (4) |
N4—C7 | 1.346 (3) | C15—H15 | 0.9500 |
N4—C11 | 1.350 (3) | C16—C17 | 1.380 (4) |
N5—C12 | 1.329 (3) | C16—H16 | 0.9500 |
N5—C13 | 1.461 (3) | C17—C18 | 1.372 (5) |
N5—H5N | 0.8800 | C17—H17 | 0.9500 |
N6—C18 | 1.342 (4) | C18—H18 | 0.9500 |
N6—C14 | 1.347 (3) | O1W—H19 | 0.85 (4) |
N6—H6N | 0.8800 | O1W—H20 | 0.82 (5) |
C1—C2 | 1.391 (3) | O2W—H21 | 0.90 (5) |
C1—C12 | 1.522 (3) | O2W—H22 | 0.88 (2) |
C2—C5 | 1.515 (3) | O3W—H23 | 0.84 (4) |
C3—C4 | 1.398 (4) | O3W—H24 | 0.82 (4) |
| | | |
N3—Cu1—O11 | 165.57 (9) | N3—C6—C7 | 107.6 (2) |
N3—Cu1—N4 | 81.69 (9) | N3—C6—H6A | 110.2 |
O11—Cu1—N4 | 100.81 (8) | C7—C6—H6A | 110.2 |
N3—Cu1—N2 | 81.08 (8) | N3—C6—H6B | 110.2 |
O11—Cu1—N2 | 95.58 (8) | C7—C6—H6B | 110.2 |
N4—Cu1—N2 | 162.72 (8) | H6A—C6—H6B | 108.5 |
N3—Cu1—O2i | 107.81 (9) | N4—C7—C8 | 121.4 (2) |
O11—Cu1—O2i | 86.39 (7) | N4—C7—C6 | 116.6 (2) |
N4—Cu1—O2i | 92.05 (8) | C8—C7—C6 | 121.9 (2) |
N2—Cu1—O2i | 94.45 (8) | C9—C8—C7 | 118.8 (3) |
O14—S1—O12 | 111.32 (12) | C9—C8—H8 | 120.6 |
O14—S1—O13 | 110.36 (11) | C7—C8—H8 | 120.6 |
O12—S1—O13 | 109.97 (11) | C8—C9—C10 | 119.6 (3) |
O14—S1—O11 | 108.83 (12) | C8—C9—H9 | 120.2 |
O12—S1—O11 | 108.07 (11) | C10—C9—H9 | 120.2 |
O13—S1—O11 | 108.20 (11) | C11—C10—C9 | 118.8 (2) |
C12—O2—Cu1i | 132.92 (15) | C11—C10—H10 | 120.6 |
S1—O11—Cu1 | 121.36 (10) | C9—C10—H10 | 120.6 |
C4—N1—C1 | 117.2 (2) | N4—C11—C10 | 122.1 (2) |
C3—N2—C2 | 119.1 (2) | N4—C11—H11 | 118.9 |
C3—N2—Cu1 | 128.92 (16) | C10—C11—H11 | 118.9 |
C2—N2—Cu1 | 111.94 (16) | O2—C12—N5 | 123.9 (2) |
C5—N3—C6 | 120.7 (2) | O2—C12—C1 | 120.1 (2) |
C5—N3—Cu1 | 120.24 (17) | N5—C12—C1 | 115.8 (2) |
C6—N3—Cu1 | 118.86 (15) | N5—C13—C14 | 113.1 (2) |
C7—N4—C11 | 119.1 (2) | N5—C13—H13A | 109.0 |
C7—N4—Cu1 | 115.18 (16) | C14—C13—H13A | 109.0 |
C11—N4—Cu1 | 125.65 (18) | N5—C13—H13B | 109.0 |
C12—N5—C13 | 121.9 (2) | C14—C13—H13B | 109.0 |
C12—N5—H5N | 119.0 | H13A—C13—H13B | 107.8 |
C13—N5—H5N | 119.0 | N6—C14—C15 | 118.6 (3) |
C18—N6—C14 | 122.6 (3) | N6—C14—C13 | 117.0 (2) |
C18—N6—H6N | 118.7 | C15—C14—C13 | 124.3 (2) |
C14—N6—H6N | 118.7 | C14—C15—C16 | 119.6 (2) |
N1—C1—C2 | 121.7 (2) | C14—C15—H15 | 120.2 |
N1—C1—C12 | 114.0 (2) | C16—C15—H15 | 120.2 |
C2—C1—C12 | 124.2 (2) | C17—C16—C15 | 119.9 (3) |
N2—C2—C1 | 119.7 (2) | C17—C16—H16 | 120.1 |
N2—C2—C5 | 115.4 (2) | C15—C16—H16 | 120.1 |
C1—C2—C5 | 125.0 (2) | C18—C17—C16 | 118.8 (3) |
N2—C3—C4 | 119.9 (2) | C18—C17—H17 | 120.6 |
N2—C3—H3 | 120.0 | C16—C17—H17 | 120.6 |
C4—C3—H3 | 120.0 | N6—C18—C17 | 120.4 (3) |
N1—C4—C3 | 122.4 (2) | N6—C18—H18 | 119.8 |
N1—C4—H4 | 118.8 | C17—C18—H18 | 119.8 |
C3—C4—H4 | 118.8 | H19—O1W—H20 | 103 (5) |
O1—C5—N3 | 129.2 (2) | H21—O2W—H22 | 109 (4) |
O1—C5—C2 | 119.5 (2) | H23—O3W—H24 | 110 (4) |
N3—C5—C2 | 111.3 (2) | | |
| | | |
O14—S1—O11—Cu1 | 140.82 (12) | N2—C3—C4—N1 | 0.3 (4) |
O12—S1—O11—Cu1 | 19.80 (15) | C6—N3—C5—O1 | 3.1 (4) |
O13—S1—O11—Cu1 | −99.24 (13) | Cu1—N3—C5—O1 | 177.5 (2) |
N3—Cu1—O11—S1 | −22.2 (4) | C6—N3—C5—C2 | −177.0 (2) |
N4—Cu1—O11—S1 | 76.48 (14) | Cu1—N3—C5—C2 | −2.6 (3) |
N2—Cu1—O11—S1 | −98.00 (13) | N2—C2—C5—O1 | −179.7 (2) |
O2i—Cu1—O11—S1 | 167.88 (13) | C1—C2—C5—O1 | 1.6 (4) |
N3—Cu1—N2—C3 | 176.7 (3) | N2—C2—C5—N3 | 0.4 (3) |
O11—Cu1—N2—C3 | −17.4 (3) | C1—C2—C5—N3 | −178.3 (3) |
N4—Cu1—N2—C3 | −178.9 (3) | C5—N3—C6—C7 | 174.9 (2) |
O2i—Cu1—N2—C3 | 69.4 (2) | Cu1—N3—C6—C7 | 0.4 (3) |
N3—Cu1—N2—C2 | −2.32 (19) | C11—N4—C7—C8 | −3.2 (4) |
O11—Cu1—N2—C2 | 163.53 (18) | Cu1—N4—C7—C8 | 178.5 (2) |
N4—Cu1—N2—C2 | 2.1 (4) | C11—N4—C7—C6 | 175.8 (2) |
O2i—Cu1—N2—C2 | −109.68 (18) | Cu1—N4—C7—C6 | −2.5 (3) |
O11—Cu1—N3—C5 | −74.7 (4) | N3—C6—C7—N4 | 1.4 (3) |
N4—Cu1—N3—C5 | −175.9 (2) | N3—C6—C7—C8 | −179.6 (3) |
N2—Cu1—N3—C5 | 2.8 (2) | N4—C7—C8—C9 | 4.0 (4) |
O2i—Cu1—N3—C5 | 94.7 (2) | C6—C7—C8—C9 | −174.9 (3) |
O11—Cu1—N3—C6 | 99.8 (4) | C7—C8—C9—C10 | −1.7 (4) |
N4—Cu1—N3—C6 | −1.3 (2) | C8—C9—C10—C11 | −1.4 (5) |
N2—Cu1—N3—C6 | 177.4 (2) | C7—N4—C11—C10 | −0.1 (4) |
O2i—Cu1—N3—C6 | −90.8 (2) | Cu1—N4—C11—C10 | 178.1 (2) |
N3—Cu1—N4—C7 | 2.1 (2) | C9—C10—C11—N4 | 2.3 (5) |
O11—Cu1—N4—C7 | −163.48 (19) | Cu1i—O2—C12—N5 | −162.33 (18) |
N2—Cu1—N4—C7 | −2.3 (4) | Cu1i—O2—C12—C1 | 13.2 (3) |
O2i—Cu1—N4—C7 | 109.8 (2) | C13—N5—C12—O2 | 2.0 (4) |
N3—Cu1—N4—C11 | −176.1 (2) | C13—N5—C12—C1 | −173.8 (2) |
O11—Cu1—N4—C11 | 18.4 (2) | N1—C1—C12—O2 | −93.9 (3) |
N2—Cu1—N4—C11 | 179.5 (3) | C2—C1—C12—O2 | 81.8 (3) |
O2i—Cu1—N4—C11 | −68.4 (2) | N1—C1—C12—N5 | 82.0 (3) |
C4—N1—C1—C2 | −1.0 (4) | C2—C1—C12—N5 | −102.3 (3) |
C4—N1—C1—C12 | 174.9 (2) | C12—N5—C13—C14 | −93.1 (3) |
C3—N2—C2—C1 | 1.3 (4) | C18—N6—C14—C15 | −2.3 (4) |
Cu1—N2—C2—C1 | −179.5 (2) | C18—N6—C14—C13 | 177.7 (3) |
C3—N2—C2—C5 | −177.5 (2) | N5—C13—C14—N6 | −159.4 (3) |
Cu1—N2—C2—C5 | 1.7 (3) | N5—C13—C14—C15 | 20.6 (4) |
N1—C1—C2—N2 | −0.1 (4) | N6—C14—C15—C16 | 2.3 (4) |
C12—C1—C2—N2 | −175.6 (3) | C13—C14—C15—C16 | −177.7 (3) |
N1—C1—C2—C5 | 178.6 (3) | C14—C15—C16—C17 | −0.6 (5) |
C12—C1—C2—C5 | 3.1 (4) | C15—C16—C17—C18 | −1.1 (5) |
C2—N2—C3—C4 | −1.4 (4) | C14—N6—C18—C17 | 0.5 (5) |
Cu1—N2—C3—C4 | 179.6 (2) | C16—C17—C18—N6 | 1.2 (5) |
C1—N1—C4—C3 | 0.9 (4) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O12ii | 0.88 | 2.05 | 2.864 (3) | 153 |
N6—H6N···O2Wiii | 0.88 | 1.77 | 2.644 (5) | 173 |
O1W—H19···O1i | 0.85 (5) | 1.93 (5) | 2.770 (4) | 172 (5) |
O1W—H20···O13iv | 0.82 (5) | 2.00 (5) | 2.821 (3) | 176 (5) |
O2W—H21···O1W | 0.90 (5) | 1.88 (5) | 2.772 (4) | 171 (4) |
O2W—H22···O3Wv | 0.88 (4) | 1.87 (4) | 2.715 (5) | 160 (5) |
O3W—H23···O13vi | 0.84 (4) | 2.00 (4) | 2.829 (3) | 171 (4) |
O3W—H24···O14vii | 0.82 (5) | 2.00 (5) | 2.817 (4) | 172 (4) |
C8—H8···O12viii | 0.95 | 2.44 | 3.280 (3) | 147 |
C9—H9···O12vii | 0.95 | 2.46 | 3.358 (5) | 158 |
C10—H10···O14vii | 0.95 | 2.52 | 3.283 (4) | 137 |
C15—H15···O1 | 0.95 | 2.16 | 3.103 (3) | 172 |
C18—H18···O11iii | 0.95 | 2.25 | 3.119 (4) | 152 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) x, y, z+1; (iv) x, y+1, z; (v) x−1, y, z; (vi) −x+1, −y, −z; (vii) x+1, y, z; (viii) −x+1, −y, −z+1. |