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Three coordination polymers based on quaternary-ammonium-modified isophthalic acid, namely, catena-poly[[[aqua-μ2-bromido-di-μ3-hydroxido-methanoldinitratotetracopper(II)]-bis{μ4-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}] nitrate], {[Cu4Br(C19H28NO5)2(NO3)2(OH)2(CH4O)(H2O)]NO3}n, 1, poly[μ3-bromido-μ2-bromido-bromido-μ3-hydroxido-{μ4-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}tricopper(II)], [Cu3Br3(C19H28NO5)(OH)]n, 2, and poly[bromido{μ3-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}zinc(II)], [ZnBr(C19H28NO5)]n, 3, were obtained by solvothermal reactions. Coordination polymer (CP) 1 contains tetranuclear Cu4 units, in which the four Cu atoms are linked by two μ3-OH− groups into a Cu4(OH)2 cluster, which are in turn linked by 5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylate (cpa−) ligands into a chain structure. CP 2 also contains a tetranuclear Cu4(OH)2 cluster and these are linked with CuBr3 units into chains. The chains are then connected by cpa− ligands into a two-dimensional layered structure. CP 3 contains a two-dimensional layer structure built by binuclear Zn2 units and cpa− ligands. The Br− counter-anions of the quaternary ammonium groups all take part in the construction of the polymeric networks.
Supporting information
CCDC references: 2026903; 2026902; 2026901
For all structures, data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b). Molecular graphics: SHELXTL (Bruker, 2015) for (1), (2); OLEX2 (Dolomanov et al., 2009) for (3). Software used to prepare material for publication: SHELXTL (Bruker, 2015) for (1), (2); OLEX2 (Dolomanov et al., 2009) for (3).
catena-Poly[[[aqua-µ
2-bromido-di-µ
3-hydroxido-methanoldinitratotetracopper(II)]-bis{µ
4-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}] nitrate] (1)
top
Crystal data top
[Cu4Br(C19H28NO5)2(NO3)2(OH)2(CH4O)(H2O)]NO3 | Z = 2 |
Mr = 1305.02 | F(000) = 1336 |
Triclinic, P1 | Dx = 1.645 Mg m−3 |
a = 9.4872 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.7297 (14) Å | Cell parameters from 3991 reflections |
c = 25.920 (2) Å | θ = 2.3–27.5° |
α = 89.116 (3)° | µ = 2.43 mm−1 |
β = 87.262 (3)° | T = 296 K |
γ = 89.258 (2)° | Block, blue |
V = 2635.0 (6) Å3 | 0.28 × 0.24 × 0.22 mm |
Data collection top
Bruker D8 diffractometer | 7239 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.093 |
ω rotation scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −8→11 |
Tmin = 0.55, Tmax = 0.62 | k = −13→13 |
22593 measured reflections | l = −31→31 |
10238 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0372P)2 + 1.0708P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
10238 reflections | Δρmax = 1.36 e Å−3 |
649 parameters | Δρmin = −0.69 e Å−3 |
0 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.76224 (4) | −0.08840 (4) | 0.17146 (2) | 0.04306 (12) | |
C1 | 1.0389 (4) | 0.2412 (3) | 0.30155 (14) | 0.0296 (8) | |
C2 | 0.9736 (4) | 0.3549 (3) | 0.29548 (13) | 0.0310 (8) | |
H2 | 0.883928 | 0.360292 | 0.282512 | 0.037* | |
C3 | 1.0436 (4) | 0.4624 (3) | 0.30907 (14) | 0.0324 (9) | |
C4 | 1.1770 (3) | 0.4564 (3) | 0.33007 (13) | 0.0281 (8) | |
H4 | 1.221738 | 0.528291 | 0.339862 | 0.034* | |
C5 | 1.2410 (4) | 0.3391 (3) | 0.33589 (14) | 0.0318 (8) | |
C6 | 1.1737 (4) | 0.2319 (3) | 0.32084 (14) | 0.0315 (8) | |
H6 | 1.218310 | 0.154517 | 0.323610 | 0.038* | |
C7 | 0.9680 (4) | 0.1232 (3) | 0.28755 (15) | 0.0338 (9) | |
C8 | 0.9745 (4) | 0.5884 (3) | 0.30102 (14) | 0.0304 (8) | |
C9 | 0.4145 (4) | 0.4745 (3) | 0.21475 (13) | 0.0288 (8) | |
C10 | 0.4777 (4) | 0.3605 (3) | 0.22694 (13) | 0.0303 (8) | |
H10 | 0.564922 | 0.357858 | 0.241893 | 0.036* | |
C11 | 0.4090 (4) | 0.2510 (3) | 0.21648 (13) | 0.0283 (8) | |
C12 | 0.2745 (4) | 0.2543 (3) | 0.19764 (13) | 0.0313 (8) | |
H12 | 0.228113 | 0.180345 | 0.191826 | 0.038* | |
C13 | 0.2100 (4) | 0.3667 (3) | 0.18759 (14) | 0.0306 (8) | |
C14 | 0.2801 (4) | 0.4787 (3) | 0.19522 (13) | 0.0312 (8) | |
H14 | 0.237538 | 0.554760 | 0.187346 | 0.037* | |
C15 | 0.4873 (4) | 0.5943 (3) | 0.22367 (14) | 0.0316 (8) | |
C16 | 0.4759 (4) | 0.1280 (3) | 0.22804 (14) | 0.0304 (8) | |
C17 | 1.4658 (4) | 0.4210 (3) | 0.36160 (14) | 0.0311 (8) | |
H17A | 1.440233 | 0.465906 | 0.392922 | 0.037* | |
H17B | 1.461458 | 0.478460 | 0.332447 | 0.037* | |
C18 | 1.6124 (4) | 0.3661 (3) | 0.36437 (14) | 0.0320 (8) | |
H18A | 1.679391 | 0.428815 | 0.352237 | 0.038* | |
H18B | 1.621114 | 0.297059 | 0.340662 | 0.038* | |
C19 | 1.6852 (4) | 0.4301 (3) | 0.45089 (14) | 0.0349 (9) | |
H19A | 1.604704 | 0.486691 | 0.450569 | 0.042* | |
H19B | 1.692205 | 0.399473 | 0.486091 | 0.042* | |
C20 | 1.8155 (4) | 0.5039 (3) | 0.43682 (15) | 0.0378 (9) | |
H20A | 1.805350 | 0.544982 | 0.403598 | 0.045* | |
H20B | 1.896648 | 0.448001 | 0.433894 | 0.045* | |
C21 | 1.8397 (4) | 0.6017 (3) | 0.47795 (15) | 0.0439 (10) | |
H21A | 1.750851 | 0.638279 | 0.489228 | 0.066* | |
H21B | 1.900393 | 0.665492 | 0.463483 | 0.066* | |
H21C | 1.883055 | 0.562634 | 0.506855 | 0.066* | |
C22 | 1.7814 (4) | 0.2375 (3) | 0.40822 (14) | 0.0334 (9) | |
H22A | 1.852699 | 0.285002 | 0.388709 | 0.040* | |
H22B | 1.755362 | 0.168928 | 0.386823 | 0.040* | |
C23 | 1.8469 (4) | 0.1840 (4) | 0.45547 (15) | 0.0387 (9) | |
H23A | 1.780496 | 0.128325 | 0.473311 | 0.046* | |
H23B | 1.866283 | 0.251045 | 0.478689 | 0.046* | |
C24 | 1.9839 (4) | 0.1125 (4) | 0.44217 (16) | 0.0507 (12) | |
H24A | 2.022223 | 0.079893 | 0.473303 | 0.076* | |
H24B | 1.964905 | 0.044971 | 0.419732 | 0.076* | |
H24C | 2.050652 | 0.167632 | 0.425108 | 0.076* | |
C25 | 1.5378 (4) | 0.2471 (3) | 0.44526 (14) | 0.0329 (9) | |
H25A | 1.452578 | 0.298029 | 0.445739 | 0.039* | |
H25B | 1.563139 | 0.234783 | 0.480817 | 0.039* | |
C26 | 1.5033 (4) | 0.1193 (3) | 0.42338 (14) | 0.0339 (9) | |
H26A | 1.489548 | 0.127153 | 0.386623 | 0.041* | |
H26B | 1.581095 | 0.061412 | 0.428356 | 0.041* | |
C27 | 1.3702 (4) | 0.0706 (3) | 0.45100 (14) | 0.0384 (9) | |
H27A | 1.391898 | 0.040179 | 0.484775 | 0.058* | |
H27B | 1.333209 | 0.003975 | 0.431578 | 0.058* | |
H27C | 1.301361 | 0.136670 | 0.454124 | 0.058* | |
C28 | −0.0036 (4) | 0.4772 (3) | 0.16589 (14) | 0.0317 (8) | |
H28A | 0.037263 | 0.530198 | 0.138605 | 0.038* | |
H28B | −0.002138 | 0.521481 | 0.198208 | 0.038* | |
C29 | −0.1512 (4) | 0.4459 (3) | 0.15460 (14) | 0.0322 (9) | |
H29A | −0.211791 | 0.513456 | 0.167181 | 0.039* | |
H29B | −0.176761 | 0.372111 | 0.174821 | 0.039* | |
C30 | −0.0945 (4) | 0.3191 (3) | 0.07699 (14) | 0.0339 (9) | |
H30A | 0.003201 | 0.342128 | 0.080100 | 0.041* | |
H30B | −0.110664 | 0.313875 | 0.040421 | 0.041* | |
C31 | −0.1145 (4) | 0.1904 (3) | 0.10100 (14) | 0.0376 (9) | |
H31A | −0.209394 | 0.161804 | 0.095920 | 0.045* | |
H31B | −0.101071 | 0.193012 | 0.137830 | 0.045* | |
C32 | −0.0061 (4) | 0.1012 (3) | 0.07508 (16) | 0.0467 (11) | |
H32A | −0.045933 | 0.064302 | 0.045671 | 0.070* | |
H32B | 0.018786 | 0.036856 | 0.099265 | 0.070* | |
H32C | 0.076844 | 0.146624 | 0.064087 | 0.070* | |
C33 | −0.3395 (4) | 0.3883 (4) | 0.10006 (14) | 0.0346 (9) | |
H33A | −0.394222 | 0.457751 | 0.114276 | 0.041* | |
H33B | −0.353412 | 0.317913 | 0.123601 | 0.041* | |
C34 | −0.3987 (4) | 0.3553 (4) | 0.04888 (14) | 0.0380 (9) | |
H34A | −0.339510 | 0.291577 | 0.032469 | 0.046* | |
H34B | −0.397276 | 0.428421 | 0.026371 | 0.046* | |
C35 | −0.5502 (4) | 0.3079 (4) | 0.05573 (16) | 0.0437 (10) | |
H35A | −0.567555 | 0.279215 | 0.090692 | 0.066* | |
H35B | −0.562728 | 0.240451 | 0.032561 | 0.066* | |
H35C | −0.615094 | 0.374389 | 0.048243 | 0.066* | |
C36 | −0.1556 (4) | 0.5353 (3) | 0.06466 (14) | 0.0340 (9) | |
H36A | −0.174318 | 0.513804 | 0.029435 | 0.041* | |
H36B | −0.055796 | 0.552988 | 0.065556 | 0.041* | |
C37 | −0.2384 (4) | 0.6543 (3) | 0.07813 (14) | 0.0385 (9) | |
H37A | −0.337760 | 0.642063 | 0.072852 | 0.046* | |
H37B | −0.228331 | 0.673187 | 0.114238 | 0.046* | |
C38 | −0.1848 (4) | 0.7631 (3) | 0.04456 (15) | 0.0395 (9) | |
H38A | −0.090688 | 0.744753 | 0.031288 | 0.059* | |
H38B | −0.184248 | 0.837088 | 0.064881 | 0.059* | |
H38C | −0.245528 | 0.775908 | 0.016334 | 0.059* | |
C39 | 0.3886 (5) | 0.9576 (4) | 0.09553 (18) | 0.0636 (14) | |
H39A | 0.396861 | 1.038965 | 0.109853 | 0.095* | |
H39B | 0.302283 | 0.953287 | 0.077779 | 0.095* | |
H39C | 0.467126 | 0.941955 | 0.071680 | 0.095* | |
Cu1 | 1.03219 (5) | −0.14911 (4) | 0.28867 (2) | 0.03475 (12) | |
Cu2 | 0.71281 (5) | −0.00817 (4) | 0.26893 (2) | 0.03171 (12) | |
Cu3 | 0.48167 (5) | 0.86298 (4) | 0.20312 (2) | 0.03553 (13) | |
Cu4 | 0.71186 (4) | 0.71910 (4) | 0.27648 (2) | 0.03062 (12) | |
N1 | 1.6544 (3) | 0.3197 (2) | 0.41718 (11) | 0.0278 (7) | |
N2 | −0.1862 (3) | 0.4223 (3) | 0.09894 (11) | 0.0321 (7) | |
N4 | 0.6185 (3) | 0.7521 (3) | 0.39588 (11) | 0.0280 (7) | |
N5 | 0.2433 (3) | 0.6385 (3) | 0.07522 (10) | 0.0270 (7) | |
O1 | 1.0475 (3) | 0.0323 (2) | 0.27743 (9) | 0.0363 (6) | |
O2 | 0.8376 (2) | 0.1253 (2) | 0.28549 (10) | 0.0337 (6) | |
O3 | 0.8548 (2) | 0.5892 (2) | 0.28186 (9) | 0.0326 (6) | |
O4 | 1.0415 (2) | 0.6799 (2) | 0.31504 (10) | 0.0357 (6) | |
O5 | 1.3712 (2) | 0.3192 (2) | 0.35568 (9) | 0.0341 (6) | |
O6 | 0.4377 (3) | 0.6897 (2) | 0.20265 (10) | 0.0370 (6) | |
O7 | 0.5985 (2) | 0.5878 (2) | 0.24809 (9) | 0.0335 (6) | |
O8 | 0.5810 (2) | 0.1280 (2) | 0.25593 (9) | 0.0320 (6) | |
O9 | 0.4235 (3) | 0.0357 (2) | 0.20695 (9) | 0.0349 (6) | |
O10 | 0.0762 (2) | 0.3625 (2) | 0.16934 (9) | 0.0319 (6) | |
O11 | 0.8280 (2) | −0.1429 (2) | 0.30013 (10) | 0.0330 (6) | |
H11A | 0.812070 | −0.138763 | 0.332611 | 0.040* | |
O12 | 0.5723 (2) | 0.8571 (2) | 0.26852 (9) | 0.0309 (6) | |
H12B | 0.513065 | 0.861025 | 0.294108 | 0.037* | |
O13 | 1.1700 (3) | −0.1094 (2) | 0.36736 (10) | 0.0409 (6) | |
N3 | 1.2706 (3) | −0.1263 (3) | 0.33455 (12) | 0.033 | |
O14 | 1.3923 (3) | −0.1094 (2) | 0.34930 (10) | 0.0415 (7) | |
O15 | 1.2455 (3) | −0.1497 (2) | 0.28878 (10) | 0.0393 (6) | |
O16 | 0.7031 (3) | 0.8405 (2) | 0.39406 (10) | 0.0385 (6) | |
O17 | 0.5397 (3) | 0.7322 (3) | 0.43481 (10) | 0.0469 (7) | |
O18 | 0.6199 (3) | 0.6777 (2) | 0.35879 (10) | 0.0378 (6) | |
O19 | 0.3877 (3) | 0.8613 (2) | 0.13820 (10) | 0.0508 (8) | |
H19 | 0.339145 | 0.796928 | 0.133238 | 0.061* | |
O20 | 0.3739 (3) | 0.6552 (2) | 0.07651 (11) | 0.0481 (7) | |
O21 | 0.1616 (3) | 0.7140 (2) | 0.09470 (11) | 0.0475 (7) | |
O22 | 0.2098 (3) | 0.5351 (3) | 0.05766 (10) | 0.0471 (7) | |
O1W | 1.0560 (3) | −0.2075 (2) | 0.20653 (10) | 0.0438 (7) | |
H1Y | 1.053435 | −0.143314 | 0.186938 | 0.053* | |
H1X | 0.988905 | −0.255594 | 0.199968 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0449 (2) | 0.0439 (2) | 0.0398 (2) | −0.00974 (19) | 0.00901 (19) | −0.01107 (18) |
C1 | 0.0255 (19) | 0.030 (2) | 0.033 (2) | −0.0082 (16) | 0.0051 (16) | −0.0087 (16) |
C2 | 0.032 (2) | 0.0258 (19) | 0.036 (2) | −0.0022 (16) | −0.0117 (17) | −0.0073 (16) |
C3 | 0.034 (2) | 0.029 (2) | 0.036 (2) | 0.0037 (16) | −0.0100 (18) | −0.0099 (16) |
C4 | 0.0215 (18) | 0.0266 (19) | 0.036 (2) | −0.0053 (15) | 0.0024 (16) | −0.0073 (15) |
C5 | 0.031 (2) | 0.029 (2) | 0.036 (2) | −0.0080 (16) | −0.0114 (17) | 0.0094 (16) |
C6 | 0.032 (2) | 0.0265 (19) | 0.036 (2) | 0.0037 (16) | −0.0101 (17) | −0.0069 (16) |
C7 | 0.035 (2) | 0.0241 (19) | 0.043 (2) | 0.0001 (17) | −0.0118 (19) | 0.0032 (16) |
C8 | 0.0263 (19) | 0.028 (2) | 0.037 (2) | 0.0034 (16) | 0.0024 (17) | −0.0105 (16) |
C9 | 0.031 (2) | 0.0260 (19) | 0.031 (2) | 0.0039 (15) | −0.0097 (17) | −0.0088 (15) |
C10 | 0.0303 (19) | 0.028 (2) | 0.033 (2) | 0.0050 (15) | −0.0101 (17) | −0.0096 (16) |
C11 | 0.0240 (18) | 0.0251 (19) | 0.035 (2) | 0.0050 (15) | 0.0041 (16) | −0.0065 (15) |
C12 | 0.035 (2) | 0.0262 (19) | 0.033 (2) | −0.0065 (16) | −0.0099 (17) | 0.0052 (16) |
C13 | 0.031 (2) | 0.0273 (19) | 0.035 (2) | 0.0038 (16) | −0.0095 (17) | −0.0097 (16) |
C14 | 0.033 (2) | 0.0270 (19) | 0.035 (2) | −0.0008 (16) | −0.0092 (17) | −0.0075 (16) |
C15 | 0.036 (2) | 0.026 (2) | 0.034 (2) | −0.0055 (16) | −0.0074 (18) | −0.0065 (16) |
C16 | 0.0230 (18) | 0.0261 (19) | 0.042 (2) | −0.0002 (15) | 0.0003 (17) | −0.0051 (17) |
C17 | 0.0298 (19) | 0.0271 (19) | 0.037 (2) | −0.0053 (16) | −0.0079 (17) | 0.0032 (16) |
C18 | 0.033 (2) | 0.029 (2) | 0.034 (2) | 0.0006 (16) | −0.0095 (17) | 0.0027 (16) |
C19 | 0.035 (2) | 0.034 (2) | 0.037 (2) | −0.0069 (17) | −0.0127 (18) | −0.0075 (17) |
C20 | 0.034 (2) | 0.038 (2) | 0.042 (2) | −0.0055 (17) | −0.0090 (19) | −0.0080 (18) |
C21 | 0.049 (2) | 0.036 (2) | 0.048 (3) | −0.0156 (19) | −0.017 (2) | −0.0059 (18) |
C22 | 0.029 (2) | 0.037 (2) | 0.033 (2) | 0.0102 (17) | 0.0041 (17) | 0.0081 (16) |
C23 | 0.031 (2) | 0.041 (2) | 0.044 (2) | 0.0080 (18) | −0.0064 (19) | 0.0072 (18) |
C24 | 0.038 (2) | 0.064 (3) | 0.048 (3) | 0.021 (2) | 0.011 (2) | 0.022 (2) |
C25 | 0.0282 (19) | 0.039 (2) | 0.032 (2) | −0.0071 (16) | −0.0077 (17) | −0.0068 (17) |
C26 | 0.036 (2) | 0.031 (2) | 0.034 (2) | −0.0040 (17) | 0.0039 (18) | 0.0067 (16) |
C27 | 0.042 (2) | 0.038 (2) | 0.034 (2) | −0.0104 (18) | 0.0087 (19) | 0.0081 (17) |
C28 | 0.0279 (19) | 0.032 (2) | 0.036 (2) | 0.0054 (16) | −0.0095 (17) | −0.0089 (16) |
C29 | 0.031 (2) | 0.034 (2) | 0.032 (2) | 0.0036 (16) | −0.0088 (17) | −0.0071 (16) |
C30 | 0.037 (2) | 0.033 (2) | 0.032 (2) | −0.0079 (17) | −0.0077 (18) | −0.0069 (16) |
C31 | 0.042 (2) | 0.034 (2) | 0.036 (2) | −0.0062 (18) | 0.0081 (19) | −0.0069 (17) |
C32 | 0.048 (3) | 0.036 (2) | 0.055 (3) | −0.005 (2) | 0.019 (2) | 0.0057 (19) |
C33 | 0.031 (2) | 0.042 (2) | 0.031 (2) | −0.0093 (17) | −0.0113 (17) | 0.0048 (17) |
C34 | 0.035 (2) | 0.043 (2) | 0.037 (2) | −0.0107 (18) | −0.0132 (19) | 0.0065 (18) |
C35 | 0.042 (2) | 0.044 (2) | 0.047 (3) | −0.0141 (19) | −0.014 (2) | −0.0101 (19) |
C36 | 0.0274 (19) | 0.038 (2) | 0.037 (2) | 0.0031 (16) | −0.0091 (17) | 0.0020 (17) |
C37 | 0.041 (2) | 0.039 (2) | 0.035 (2) | 0.0033 (18) | 0.0064 (19) | 0.0055 (17) |
C38 | 0.036 (2) | 0.040 (2) | 0.042 (2) | 0.0081 (18) | 0.0092 (19) | 0.0080 (18) |
C39 | 0.092 (4) | 0.040 (3) | 0.061 (3) | −0.008 (2) | −0.032 (3) | 0.011 (2) |
Cu1 | 0.0321 (3) | 0.0276 (2) | 0.0454 (3) | 0.00527 (19) | −0.0097 (2) | −0.0091 (2) |
Cu2 | 0.0314 (2) | 0.0257 (2) | 0.0391 (3) | 0.00473 (19) | −0.0119 (2) | −0.00869 (19) |
Cu3 | 0.0420 (3) | 0.0264 (2) | 0.0397 (3) | 0.0055 (2) | −0.0169 (2) | −0.0087 (2) |
Cu4 | 0.0306 (2) | 0.0260 (2) | 0.0362 (3) | 0.00506 (19) | −0.0107 (2) | −0.00862 (19) |
N1 | 0.0262 (16) | 0.0268 (16) | 0.0302 (17) | 0.0048 (13) | 0.0002 (13) | −0.0047 (13) |
N2 | 0.0308 (17) | 0.0330 (17) | 0.0336 (17) | −0.0093 (14) | −0.0085 (14) | −0.0054 (13) |
N4 | 0.0287 (17) | 0.0357 (18) | 0.0201 (17) | 0.0039 (14) | −0.0083 (14) | 0.0086 (14) |
N5 | 0.0287 (17) | 0.0333 (17) | 0.0191 (16) | −0.0197 (14) | 0.0045 (13) | −0.0074 (13) |
O1 | 0.0347 (15) | 0.0306 (14) | 0.0428 (16) | 0.0043 (12) | 0.0070 (12) | −0.0083 (11) |
O2 | 0.0305 (14) | 0.0271 (13) | 0.0447 (16) | −0.0050 (11) | −0.0102 (12) | −0.0086 (11) |
O3 | 0.0308 (14) | 0.0267 (13) | 0.0415 (15) | −0.0025 (11) | −0.0108 (12) | −0.0083 (11) |
O4 | 0.0319 (14) | 0.0306 (14) | 0.0460 (16) | −0.0064 (11) | −0.0124 (13) | −0.0069 (12) |
O5 | 0.0324 (14) | 0.0307 (14) | 0.0404 (15) | −0.0081 (11) | −0.0140 (12) | 0.0088 (11) |
O6 | 0.0421 (15) | 0.0284 (14) | 0.0424 (16) | −0.0055 (12) | −0.0197 (13) | −0.0047 (11) |
O7 | 0.0351 (14) | 0.0278 (13) | 0.0388 (15) | −0.0100 (11) | −0.0138 (12) | 0.0059 (11) |
O8 | 0.0323 (14) | 0.0222 (13) | 0.0422 (15) | −0.0048 (11) | −0.0093 (12) | 0.0034 (11) |
O9 | 0.0370 (15) | 0.0261 (13) | 0.0430 (16) | 0.0087 (11) | −0.0161 (13) | −0.0100 (11) |
O10 | 0.0302 (13) | 0.0286 (13) | 0.0381 (15) | 0.0025 (11) | −0.0142 (12) | −0.0085 (11) |
O11 | 0.0334 (14) | 0.0263 (13) | 0.0406 (15) | 0.0038 (11) | −0.0116 (12) | −0.0105 (11) |
O12 | 0.0293 (13) | 0.0291 (13) | 0.0346 (14) | 0.0015 (11) | −0.0072 (11) | 0.0010 (11) |
O13 | 0.0389 (15) | 0.0444 (16) | 0.0398 (15) | 0.0103 (13) | −0.0052 (13) | −0.0122 (12) |
N3 | 0.035 | 0.025 | 0.039 | 0.001 | 0.010 | 0.006 |
O14 | 0.0259 (14) | 0.0526 (17) | 0.0470 (17) | 0.0060 (12) | −0.0092 (13) | −0.0144 (13) |
O15 | 0.0375 (15) | 0.0442 (16) | 0.0355 (15) | 0.0059 (12) | 0.0068 (12) | −0.0130 (12) |
O16 | 0.0387 (15) | 0.0380 (15) | 0.0397 (16) | 0.0034 (13) | −0.0094 (13) | −0.0085 (12) |
O17 | 0.0470 (18) | 0.0542 (18) | 0.0378 (16) | 0.0127 (14) | 0.0080 (14) | 0.0078 (13) |
O18 | 0.0436 (16) | 0.0346 (15) | 0.0349 (15) | −0.0094 (12) | 0.0033 (13) | 0.0044 (12) |
O19 | 0.076 (2) | 0.0297 (15) | 0.0496 (17) | 0.0094 (14) | −0.0333 (16) | −0.0077 (12) |
O20 | 0.0410 (16) | 0.0478 (17) | 0.0567 (19) | −0.0101 (13) | −0.0090 (15) | −0.0153 (14) |
O21 | 0.0410 (17) | 0.0404 (17) | 0.0619 (19) | −0.0083 (14) | −0.0097 (15) | 0.0053 (14) |
O22 | 0.0434 (16) | 0.0565 (18) | 0.0414 (17) | −0.0136 (14) | 0.0076 (13) | −0.0143 (14) |
O1W | 0.0507 (17) | 0.0348 (15) | 0.0454 (17) | 0.0033 (13) | 0.0047 (14) | −0.0102 (12) |
Geometric parameters (Å, º) top
Br1—Cu2 | 2.6994 (6) | C28—H28A | 0.9700 |
Br1—Cu3i | 2.8009 (7) | C28—H28B | 0.9700 |
C1—C2 | 1.371 (5) | C29—N2 | 1.521 (4) |
C1—C6 | 1.397 (5) | C29—H29A | 0.9700 |
C1—C7 | 1.499 (5) | C29—H29B | 0.9700 |
C2—C3 | 1.397 (5) | C30—N2 | 1.501 (4) |
C2—H2 | 0.9300 | C30—C31 | 1.517 (5) |
C3—C4 | 1.402 (5) | C30—H30A | 0.9700 |
C3—C8 | 1.511 (5) | C30—H30B | 0.9700 |
C4—C5 | 1.399 (5) | C31—C32 | 1.535 (5) |
C4—H4 | 0.9300 | C31—H31A | 0.9700 |
C5—O5 | 1.373 (4) | C31—H31B | 0.9700 |
C5—C6 | 1.393 (5) | C32—H32A | 0.9600 |
C6—H6 | 0.9300 | C32—H32B | 0.9600 |
C7—O2 | 1.241 (4) | C32—H32C | 0.9600 |
C7—O1 | 1.249 (4) | C33—N2 | 1.502 (4) |
C8—O4 | 1.245 (4) | C33—C34 | 1.514 (5) |
C8—O3 | 1.260 (4) | C33—H33A | 0.9700 |
C9—C14 | 1.394 (5) | C33—H33B | 0.9700 |
C9—C10 | 1.394 (4) | C34—C35 | 1.531 (5) |
C9—C15 | 1.493 (5) | C34—H34A | 0.9700 |
C10—C11 | 1.388 (5) | C34—H34B | 0.9700 |
C10—H10 | 0.9300 | C35—H35A | 0.9600 |
C11—C12 | 1.388 (5) | C35—H35B | 0.9600 |
C11—C16 | 1.489 (5) | C35—H35C | 0.9600 |
C12—C13 | 1.372 (5) | C36—N2 | 1.514 (4) |
C12—H12 | 0.9300 | C36—C37 | 1.527 (5) |
C13—O10 | 1.377 (4) | C36—H36A | 0.9700 |
C13—C14 | 1.403 (5) | C36—H36B | 0.9700 |
C14—H14 | 0.9300 | C37—C38 | 1.523 (5) |
C15—O6 | 1.249 (4) | C37—H37A | 0.9700 |
C15—O7 | 1.256 (4) | C37—H37B | 0.9700 |
C16—O9 | 1.257 (4) | C38—H38A | 0.9600 |
C16—O8 | 1.260 (4) | C38—H38B | 0.9600 |
C17—O5 | 1.437 (4) | C38—H38C | 0.9600 |
C17—C18 | 1.507 (5) | C39—O19 | 1.501 (5) |
C17—H17A | 0.9700 | C39—H39A | 0.9600 |
C17—H17B | 0.9700 | C39—H39B | 0.9600 |
C18—N1 | 1.519 (4) | C39—H39C | 0.9600 |
C18—H18A | 0.9700 | Cu1—O11 | 1.946 (2) |
C18—H18B | 0.9700 | Cu1—O4i | 1.950 (2) |
C19—C20 | 1.504 (5) | Cu1—O1 | 1.970 (2) |
C19—N1 | 1.522 (4) | Cu1—O15 | 2.023 (3) |
C19—H19A | 0.9700 | Cu1—O1W | 2.229 (2) |
C19—H19B | 0.9700 | Cu2—O2 | 1.937 (2) |
C20—C21 | 1.535 (5) | Cu2—O8 | 1.947 (2) |
C20—H20A | 0.9700 | Cu2—O12i | 1.979 (2) |
C20—H20B | 0.9700 | Cu2—O11 | 1.986 (2) |
C21—H21A | 0.9600 | Cu2—Cu4i | 2.9300 (7) |
C21—H21B | 0.9600 | Cu3—O6 | 1.911 (2) |
C21—H21C | 0.9600 | Cu3—O9ii | 1.930 (2) |
C22—N1 | 1.496 (4) | Cu3—O12 | 1.937 (2) |
C22—C23 | 1.503 (5) | Cu3—O19 | 1.942 (2) |
C22—H22A | 0.9700 | Cu4—O3 | 1.940 (2) |
C22—H22B | 0.9700 | Cu4—O7 | 1.957 (2) |
C23—C24 | 1.529 (5) | Cu4—O11ii | 1.979 (2) |
C23—H23A | 0.9700 | Cu4—O12 | 1.988 (2) |
C23—H23B | 0.9700 | Cu4—O18 | 2.305 (2) |
C24—H24A | 0.9600 | N4—O17 | 1.244 (4) |
C24—H24B | 0.9600 | N4—O16 | 1.250 (4) |
C24—H24C | 0.9600 | N4—O18 | 1.258 (4) |
C25—N1 | 1.512 (4) | N5—O21 | 1.213 (4) |
C25—C26 | 1.538 (5) | N5—O22 | 1.256 (4) |
C25—H25A | 0.9700 | N5—O20 | 1.256 (4) |
C25—H25B | 0.9700 | O11—H11A | 0.8499 |
C26—C27 | 1.516 (5) | O12—H12B | 0.8501 |
C26—H26A | 0.9700 | O13—N3 | 1.260 (4) |
C26—H26B | 0.9700 | N3—O14 | 1.251 (4) |
C27—H27A | 0.9600 | N3—O15 | 1.251 (4) |
C27—H27B | 0.9600 | O19—H19 | 0.8500 |
C27—H27C | 0.9600 | O1W—H1Y | 0.8501 |
C28—O10 | 1.440 (4) | O1W—H1X | 0.8500 |
C28—C29 | 1.488 (5) | | |
| | | |
Cu2—Br1—Cu3i | 70.719 (16) | H32B—C32—H32C | 109.5 |
C2—C1—C6 | 121.0 (3) | N2—C33—C34 | 116.5 (3) |
C2—C1—C7 | 121.0 (3) | N2—C33—H33A | 108.2 |
C6—C1—C7 | 118.0 (3) | C34—C33—H33A | 108.2 |
C1—C2—C3 | 119.0 (3) | N2—C33—H33B | 108.2 |
C1—C2—H2 | 120.5 | C34—C33—H33B | 108.2 |
C3—C2—H2 | 120.5 | H33A—C33—H33B | 107.3 |
C2—C3—C4 | 121.6 (3) | C33—C34—C35 | 111.7 (3) |
C2—C3—C8 | 119.4 (3) | C33—C34—H34A | 109.3 |
C4—C3—C8 | 119.0 (3) | C35—C34—H34A | 109.3 |
C5—C4—C3 | 118.1 (3) | C33—C34—H34B | 109.3 |
C5—C4—H4 | 120.9 | C35—C34—H34B | 109.3 |
C3—C4—H4 | 120.9 | H34A—C34—H34B | 107.9 |
O5—C5—C6 | 114.9 (3) | C34—C35—H35A | 109.5 |
O5—C5—C4 | 124.5 (3) | C34—C35—H35B | 109.5 |
C6—C5—C4 | 120.6 (3) | H35A—C35—H35B | 109.5 |
C5—C6—C1 | 119.6 (3) | C34—C35—H35C | 109.5 |
C5—C6—H6 | 120.2 | H35A—C35—H35C | 109.5 |
C1—C6—H6 | 120.2 | H35B—C35—H35C | 109.5 |
O2—C7—O1 | 126.0 (3) | N2—C36—C37 | 116.4 (3) |
O2—C7—C1 | 117.8 (3) | N2—C36—H36A | 108.2 |
O1—C7—C1 | 116.1 (3) | C37—C36—H36A | 108.2 |
O4—C8—O3 | 127.3 (3) | N2—C36—H36B | 108.2 |
O4—C8—C3 | 116.0 (3) | C37—C36—H36B | 108.2 |
O3—C8—C3 | 116.7 (3) | H36A—C36—H36B | 107.3 |
C14—C9—C10 | 120.4 (3) | C38—C37—C36 | 110.5 (3) |
C14—C9—C15 | 118.8 (3) | C38—C37—H37A | 109.6 |
C10—C9—C15 | 120.8 (3) | C36—C37—H37A | 109.6 |
C11—C10—C9 | 119.2 (3) | C38—C37—H37B | 109.6 |
C11—C10—H10 | 120.4 | C36—C37—H37B | 109.6 |
C9—C10—H10 | 120.4 | H37A—C37—H37B | 108.1 |
C12—C11—C10 | 120.7 (3) | C37—C38—H38A | 109.5 |
C12—C11—C16 | 119.1 (3) | C37—C38—H38B | 109.5 |
C10—C11—C16 | 120.2 (3) | H38A—C38—H38B | 109.5 |
C13—C12—C11 | 120.0 (3) | C37—C38—H38C | 109.5 |
C13—C12—H12 | 120.0 | H38A—C38—H38C | 109.5 |
C11—C12—H12 | 120.0 | H38B—C38—H38C | 109.5 |
C12—C13—O10 | 116.7 (3) | O19—C39—H39A | 109.5 |
C12—C13—C14 | 120.5 (3) | O19—C39—H39B | 109.5 |
O10—C13—C14 | 122.9 (3) | H39A—C39—H39B | 109.5 |
C9—C14—C13 | 119.1 (3) | O19—C39—H39C | 109.5 |
C9—C14—H14 | 120.4 | H39A—C39—H39C | 109.5 |
C13—C14—H14 | 120.4 | H39B—C39—H39C | 109.5 |
O6—C15—O7 | 126.3 (3) | O11—Cu1—O4i | 91.71 (10) |
O6—C15—C9 | 116.6 (3) | O11—Cu1—O1 | 93.74 (10) |
O7—C15—C9 | 116.9 (3) | O4i—Cu1—O1 | 165.90 (10) |
O9—C16—O8 | 127.2 (3) | O11—Cu1—O15 | 170.94 (10) |
O9—C16—C11 | 115.7 (3) | O4i—Cu1—O15 | 86.94 (10) |
O8—C16—C11 | 117.1 (3) | O1—Cu1—O15 | 85.63 (10) |
O5—C17—C18 | 107.3 (3) | O11—Cu1—O1W | 102.00 (10) |
O5—C17—H17A | 110.3 | O4i—Cu1—O1W | 93.16 (10) |
C18—C17—H17A | 110.3 | O1—Cu1—O1W | 98.39 (10) |
O5—C17—H17B | 110.3 | O15—Cu1—O1W | 87.03 (10) |
C18—C17—H17B | 110.3 | O2—Cu2—O8 | 83.53 (10) |
H17A—C17—H17B | 108.5 | O2—Cu2—O12i | 167.24 (11) |
C17—C18—N1 | 116.2 (3) | O8—Cu2—O12i | 96.18 (9) |
C17—C18—H18A | 108.2 | O2—Cu2—O11 | 95.31 (10) |
N1—C18—H18A | 108.2 | O8—Cu2—O11 | 165.71 (10) |
C17—C18—H18B | 108.2 | O12i—Cu2—O11 | 81.81 (9) |
N1—C18—H18B | 108.2 | O2—Cu2—Br1 | 112.04 (8) |
H18A—C18—H18B | 107.4 | O8—Cu2—Br1 | 99.64 (7) |
C20—C19—N1 | 117.4 (3) | O12i—Cu2—Br1 | 80.63 (7) |
C20—C19—H19A | 108.0 | O11—Cu2—Br1 | 94.01 (7) |
N1—C19—H19A | 108.0 | O2—Cu2—Cu4i | 137.27 (7) |
C20—C19—H19B | 108.0 | O8—Cu2—Cu4i | 138.55 (7) |
N1—C19—H19B | 108.0 | O12i—Cu2—Cu4i | 42.51 (6) |
H19A—C19—H19B | 107.2 | O11—Cu2—Cu4i | 42.26 (7) |
C19—C20—C21 | 110.6 (3) | Br1—Cu2—Cu4i | 74.454 (16) |
C19—C20—H20A | 109.5 | O6—Cu3—O9ii | 150.80 (11) |
C21—C20—H20A | 109.5 | O6—Cu3—O12 | 95.66 (10) |
C19—C20—H20B | 109.5 | O9ii—Cu3—O12 | 96.06 (10) |
C21—C20—H20B | 109.5 | O6—Cu3—O19 | 81.80 (10) |
H20A—C20—H20B | 108.1 | O9ii—Cu3—O19 | 85.99 (10) |
C20—C21—H21A | 109.5 | O12—Cu3—O19 | 177.41 (11) |
C20—C21—H21B | 109.5 | O6—Cu3—Br1ii | 113.09 (8) |
H21A—C21—H21B | 109.5 | O9ii—Cu3—Br1ii | 95.42 (8) |
C20—C21—H21C | 109.5 | O12—Cu3—Br1ii | 78.67 (7) |
H21A—C21—H21C | 109.5 | O19—Cu3—Br1ii | 102.75 (9) |
H21B—C21—H21C | 109.5 | O3—Cu4—O7 | 84.65 (10) |
N1—C22—C23 | 116.5 (3) | O3—Cu4—O11ii | 96.59 (9) |
N1—C22—H22A | 108.2 | O7—Cu4—O11ii | 175.88 (10) |
C23—C22—H22A | 108.2 | O3—Cu4—O12 | 177.00 (10) |
N1—C22—H22B | 108.2 | O7—Cu4—O12 | 96.81 (10) |
C23—C22—H22B | 108.2 | O11ii—Cu4—O12 | 81.78 (9) |
H22A—C22—H22B | 107.3 | O3—Cu4—O18 | 92.22 (10) |
C22—C23—C24 | 112.1 (3) | O7—Cu4—O18 | 91.32 (10) |
C22—C23—H23A | 109.2 | O11ii—Cu4—O18 | 92.55 (10) |
C24—C23—H23A | 109.2 | O12—Cu4—O18 | 90.36 (9) |
C22—C23—H23B | 109.2 | O3—Cu4—Cu2ii | 135.35 (7) |
C24—C23—H23B | 109.2 | O7—Cu4—Cu2ii | 134.90 (7) |
H23A—C23—H23B | 107.9 | O11ii—Cu4—Cu2ii | 42.46 (6) |
C23—C24—H24A | 109.5 | O12—Cu4—Cu2ii | 42.28 (7) |
C23—C24—H24B | 109.5 | O18—Cu4—Cu2ii | 104.16 (6) |
H24A—C24—H24B | 109.5 | C22—N1—C25 | 109.8 (3) |
C23—C24—H24C | 109.5 | C22—N1—C18 | 106.5 (3) |
H24A—C24—H24C | 109.5 | C25—N1—C18 | 112.2 (3) |
H24B—C24—H24C | 109.5 | C22—N1—C19 | 111.9 (3) |
N1—C25—C26 | 116.9 (3) | C25—N1—C19 | 106.8 (3) |
N1—C25—H25A | 108.1 | C18—N1—C19 | 109.7 (3) |
C26—C25—H25A | 108.1 | C30—N2—C33 | 111.2 (3) |
N1—C25—H25B | 108.1 | C30—N2—C36 | 105.7 (3) |
C26—C25—H25B | 108.1 | C33—N2—C36 | 111.8 (3) |
H25A—C25—H25B | 107.3 | C30—N2—C29 | 110.2 (3) |
C27—C26—C25 | 109.1 (3) | C33—N2—C29 | 106.5 (3) |
C27—C26—H26A | 109.9 | C36—N2—C29 | 111.5 (3) |
C25—C26—H26A | 109.9 | O17—N4—O16 | 121.2 (3) |
C27—C26—H26B | 109.9 | O17—N4—O18 | 119.8 (3) |
C25—C26—H26B | 109.9 | O16—N4—O18 | 118.9 (3) |
H26A—C26—H26B | 108.3 | O21—N5—O22 | 125.2 (3) |
C26—C27—H27A | 109.5 | O21—N5—O20 | 119.8 (3) |
C26—C27—H27B | 109.5 | O22—N5—O20 | 114.6 (3) |
H27A—C27—H27B | 109.5 | C7—O1—Cu1 | 134.1 (2) |
C26—C27—H27C | 109.5 | C7—O2—Cu2 | 128.9 (2) |
H27A—C27—H27C | 109.5 | C8—O3—Cu4 | 131.8 (2) |
H27B—C27—H27C | 109.5 | C8—O4—Cu1ii | 127.8 (2) |
O10—C28—C29 | 108.1 (3) | C5—O5—C17 | 120.8 (3) |
O10—C28—H28A | 110.1 | C15—O6—Cu3 | 134.3 (2) |
C29—C28—H28A | 110.1 | C15—O7—Cu4 | 130.7 (2) |
O10—C28—H28B | 110.1 | C16—O8—Cu2 | 128.2 (2) |
C29—C28—H28B | 110.1 | C16—O9—Cu3i | 132.1 (2) |
H28A—C28—H28B | 108.4 | C13—O10—C28 | 118.3 (3) |
C28—C29—N2 | 118.8 (3) | Cu1—O11—Cu4i | 119.97 (11) |
C28—C29—H29A | 107.6 | Cu1—O11—Cu2 | 121.16 (13) |
N2—C29—H29A | 107.6 | Cu4i—O11—Cu2 | 95.27 (10) |
C28—C29—H29B | 107.6 | Cu1—O11—H11A | 106.3 |
N2—C29—H29B | 107.6 | Cu4i—O11—H11A | 106.3 |
H29A—C29—H29B | 107.1 | Cu2—O11—H11A | 106.3 |
N2—C30—C31 | 116.9 (3) | Cu3—O12—Cu2ii | 108.78 (11) |
N2—C30—H30A | 108.1 | Cu3—O12—Cu4 | 115.23 (12) |
C31—C30—H30A | 108.1 | Cu2ii—O12—Cu4 | 95.21 (10) |
N2—C30—H30B | 108.1 | Cu3—O12—H12B | 112.2 |
C31—C30—H30B | 108.1 | Cu2ii—O12—H12B | 112.1 |
H30A—C30—H30B | 107.3 | Cu4—O12—H12B | 112.1 |
C30—C31—C32 | 108.4 (3) | O14—N3—O15 | 123.0 (3) |
C30—C31—H31A | 110.0 | O14—N3—O13 | 116.8 (3) |
C32—C31—H31A | 110.0 | O15—N3—O13 | 120.0 (3) |
C30—C31—H31B | 110.0 | N3—O15—Cu1 | 103.8 (2) |
C32—C31—H31B | 110.0 | N4—O18—Cu4 | 125.4 (2) |
H31A—C31—H31B | 108.4 | C39—O19—Cu3 | 129.2 (2) |
C31—C32—H32A | 109.5 | C39—O19—H19 | 115.4 |
C31—C32—H32B | 109.5 | Cu3—O19—H19 | 115.4 |
H32A—C32—H32B | 109.5 | Cu1—O1W—H1Y | 109.3 |
C31—C32—H32C | 109.5 | Cu1—O1W—H1X | 109.3 |
H32A—C32—H32C | 109.5 | H1Y—O1W—H1X | 109.5 |
| | | |
C6—C1—C2—C3 | −0.2 (6) | C23—C22—N1—C18 | 177.5 (3) |
C7—C1—C2—C3 | 180.0 (3) | C23—C22—N1—C19 | 57.6 (4) |
C1—C2—C3—C4 | −1.8 (6) | C26—C25—N1—C22 | −49.0 (4) |
C1—C2—C3—C8 | 178.1 (3) | C26—C25—N1—C18 | 69.2 (4) |
C2—C3—C4—C5 | 1.7 (5) | C26—C25—N1—C19 | −170.5 (3) |
C8—C3—C4—C5 | −178.2 (3) | C17—C18—N1—C22 | 163.6 (3) |
C3—C4—C5—O5 | 179.8 (3) | C17—C18—N1—C25 | 43.4 (4) |
C3—C4—C5—C6 | 0.4 (5) | C17—C18—N1—C19 | −75.1 (4) |
O5—C5—C6—C1 | 178.2 (3) | C20—C19—N1—C22 | 48.5 (4) |
C4—C5—C6—C1 | −2.4 (6) | C20—C19—N1—C25 | 168.6 (3) |
C2—C1—C6—C5 | 2.3 (6) | C20—C19—N1—C18 | −69.6 (4) |
C7—C1—C6—C5 | −177.9 (3) | C31—C30—N2—C33 | −52.6 (4) |
C2—C1—C7—O2 | −21.3 (5) | C31—C30—N2—C36 | −174.2 (3) |
C6—C1—C7—O2 | 158.8 (3) | C31—C30—N2—C29 | 65.3 (4) |
C2—C1—C7—O1 | 156.5 (3) | C34—C33—N2—C30 | −57.6 (4) |
C6—C1—C7—O1 | −23.4 (5) | C34—C33—N2—C36 | 60.3 (4) |
C2—C3—C8—O4 | 178.5 (3) | C34—C33—N2—C29 | −177.7 (3) |
C4—C3—C8—O4 | −1.5 (5) | C37—C36—N2—C30 | 178.9 (3) |
C2—C3—C8—O3 | −0.3 (5) | C37—C36—N2—C33 | 57.7 (4) |
C4—C3—C8—O3 | 179.7 (3) | C37—C36—N2—C29 | −61.3 (4) |
C14—C9—C10—C11 | 3.9 (5) | C28—C29—N2—C30 | 57.0 (4) |
C15—C9—C10—C11 | −177.8 (3) | C28—C29—N2—C33 | 177.8 (3) |
C9—C10—C11—C12 | −4.7 (5) | C28—C29—N2—C36 | −60.0 (4) |
C9—C10—C11—C16 | 178.6 (3) | O2—C7—O1—Cu1 | −36.9 (6) |
C10—C11—C12—C13 | 2.1 (6) | C1—C7—O1—Cu1 | 145.5 (3) |
C16—C11—C12—C13 | 178.9 (3) | O1—C7—O2—Cu2 | 2.5 (6) |
C11—C12—C13—O10 | −179.5 (3) | C1—C7—O2—Cu2 | −179.9 (2) |
C11—C12—C13—C14 | 1.3 (6) | O4—C8—O3—Cu4 | −12.0 (6) |
C10—C9—C14—C13 | −0.5 (5) | C3—C8—O3—Cu4 | 166.6 (2) |
C15—C9—C14—C13 | −178.9 (3) | O3—C8—O4—Cu1ii | −27.8 (6) |
C12—C13—C14—C9 | −2.1 (5) | C3—C8—O4—Cu1ii | 153.6 (2) |
O10—C13—C14—C9 | 178.8 (3) | C6—C5—O5—C17 | 165.6 (3) |
C14—C9—C15—O6 | −15.4 (5) | C4—C5—O5—C17 | −13.9 (5) |
C10—C9—C15—O6 | 166.3 (3) | C18—C17—O5—C5 | −159.1 (3) |
C14—C9—C15—O7 | 170.0 (3) | O7—C15—O6—Cu3 | −9.0 (6) |
C10—C9—C15—O7 | −8.4 (5) | C9—C15—O6—Cu3 | 176.9 (2) |
C12—C11—C16—O9 | 18.9 (5) | O6—C15—O7—Cu4 | 15.5 (6) |
C10—C11—C16—O9 | −164.3 (3) | C9—C15—O7—Cu4 | −170.4 (2) |
C12—C11—C16—O8 | −163.7 (3) | O9—C16—O8—Cu2 | 8.6 (6) |
C10—C11—C16—O8 | 13.1 (5) | C11—C16—O8—Cu2 | −168.4 (2) |
O5—C17—C18—N1 | −84.5 (4) | O8—C16—O9—Cu3i | −4.7 (6) |
N1—C19—C20—C21 | −173.6 (3) | C11—C16—O9—Cu3i | 172.4 (2) |
N1—C22—C23—C24 | −174.3 (3) | C12—C13—O10—C28 | 170.6 (3) |
N1—C25—C26—C27 | −171.0 (3) | C14—C13—O10—C28 | −10.3 (5) |
O10—C28—C29—N2 | −82.6 (4) | C29—C28—O10—C13 | −169.9 (3) |
N2—C30—C31—C32 | −177.0 (3) | O14—N3—O15—Cu1 | −174.4 (3) |
N2—C33—C34—C35 | 173.4 (3) | O13—N3—O15—Cu1 | 0.1 (3) |
N2—C36—C37—C38 | 173.4 (3) | O17—N4—O18—Cu4 | 163.9 (2) |
C23—C22—N1—C25 | −60.8 (4) | O16—N4—O18—Cu4 | −20.5 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
Poly[µ
3-bromido-µ
2-bromido-bromido-µ
3-hydroxido-{µ
4-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}tricopper(II)] (2)
top
Crystal data top
[Cu3Br3(C19H28NO5)(OH)] | F(000) = 1560 |
Mr = 797.78 | Dx = 2.058 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0572 (7) Å | Cell parameters from 2591 reflections |
b = 10.6773 (8) Å | θ = 2.3–25.0° |
c = 26.743 (2) Å | µ = 7.15 mm−1 |
β = 95.505 (3)° | T = 296 K |
V = 2574.3 (4) Å3 | Block, blue |
Z = 4 | 0.24 × 0.22 × 0.20 mm |
Data collection top
Bruker D8 diffractometer | 4679 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.049 |
ω rotation scans | θmax = 27.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −11→9 |
Tmin = 0.3, Tmax = 0.33 | k = −13→12 |
21720 measured reflections | l = −34→26 |
5829 independent reflections | |
Refinement top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.45 | (Δ/σ)max = 0.001 |
5829 reflections | Δρmax = 0.92 e Å−3 |
293 parameters | Δρmin = −0.85 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.49074 (5) | 0.70580 (4) | 0.33094 (2) | 0.04541 (13) | |
Br2 | 0.76974 (5) | 0.54985 (4) | 0.42784 (2) | 0.04482 (13) | |
Br3 | 0.94983 (5) | 0.84742 (4) | 0.37787 (2) | 0.04260 (12) | |
C1 | 0.5677 (4) | 0.3873 (3) | 0.20284 (15) | 0.0295 (8) | |
C2 | 0.4955 (4) | 0.2816 (3) | 0.21317 (16) | 0.0353 (9) | |
H2 | 0.403807 | 0.285585 | 0.226058 | 0.042* | |
C3 | 0.5610 (4) | 0.1638 (3) | 0.20417 (17) | 0.0371 (10) | |
C4 | 0.7003 (5) | 0.1551 (4) | 0.18775 (16) | 0.0389 (10) | |
H4 | 0.744870 | 0.078130 | 0.182947 | 0.047* | |
C5 | 0.7717 (5) | 0.2687 (4) | 0.17863 (16) | 0.0393 (10) | |
C6 | 0.7110 (4) | 0.3813 (4) | 0.18600 (16) | 0.0372 (10) | |
H6 | 0.762543 | 0.454337 | 0.180121 | 0.045* | |
C7 | 0.4990 (4) | 0.5118 (3) | 0.21394 (16) | 0.0352 (9) | |
C8 | 0.4835 (5) | 0.0482 (4) | 0.22022 (17) | 0.0383 (10) | |
C9 | 1.0009 (4) | 0.3587 (3) | 0.15639 (16) | 0.0371 (10) | |
H9A | 1.009783 | 0.406106 | 0.187466 | 0.045* | |
H9B | 0.957392 | 0.412369 | 0.129664 | 0.045* | |
C10 | 1.1503 (4) | 0.3139 (4) | 0.14459 (17) | 0.0399 (10) | |
H10A | 1.171253 | 0.235492 | 0.162188 | 0.048* | |
H10B | 1.223805 | 0.374200 | 0.158010 | 0.048* | |
C11 | 1.0520 (5) | 0.2029 (3) | 0.06514 (18) | 0.0406 (10) | |
H11A | 0.954489 | 0.236011 | 0.069670 | 0.049* | |
H11B | 1.060596 | 0.196880 | 0.029343 | 0.049* | |
C12 | 1.0671 (4) | 0.0721 (3) | 0.08840 (17) | 0.0380 (10) | |
H12A | 1.073624 | 0.077623 | 0.124748 | 0.046* | |
H12B | 1.155796 | 0.031290 | 0.078847 | 0.046* | |
C13 | 0.9280 (4) | −0.0024 (3) | 0.06848 (16) | 0.0417 (11) | |
H13A | 0.848885 | 0.054719 | 0.058314 | 0.063* | |
H13B | 0.898544 | −0.056186 | 0.094502 | 0.063* | |
H13C | 0.949987 | −0.052040 | 0.040202 | 0.063* | |
C14 | 1.1482 (4) | 0.4192 (3) | 0.06235 (17) | 0.0401 (10) | |
H14A | 1.149273 | 0.405516 | 0.026524 | 0.048* | |
H14B | 1.050371 | 0.450061 | 0.067894 | 0.048* | |
C15 | 1.2596 (5) | 0.5199 (4) | 0.07801 (17) | 0.0441 (11) | |
H15A | 1.358590 | 0.491897 | 0.072460 | 0.053* | |
H15B | 1.257691 | 0.538243 | 0.113465 | 0.053* | |
C16 | 1.2199 (5) | 0.6369 (4) | 0.04691 (17) | 0.0434 (11) | |
H16A | 1.159748 | 0.613956 | 0.016781 | 0.065* | |
H16B | 1.309061 | 0.676634 | 0.038258 | 0.065* | |
H16C | 1.165796 | 0.693905 | 0.066103 | 0.065* | |
C17 | 1.3255 (4) | 0.2456 (4) | 0.08675 (17) | 0.0392 (10) | |
H17A | 1.339058 | 0.172071 | 0.107980 | 0.047* | |
H17B | 1.394549 | 0.309058 | 0.100526 | 0.047* | |
C18 | 1.3636 (5) | 0.2121 (4) | 0.03482 (17) | 0.0398 (10) | |
H18A | 1.349824 | 0.284272 | 0.012847 | 0.048* | |
H18B | 1.299269 | 0.145429 | 0.021050 | 0.048* | |
C19 | 1.5272 (4) | 0.1689 (4) | 0.03840 (17) | 0.0426 (11) | |
H19A | 1.589079 | 0.231609 | 0.055440 | 0.064* | |
H19B | 1.556656 | 0.156507 | 0.005216 | 0.064* | |
H19C | 1.537459 | 0.091608 | 0.056775 | 0.064* | |
Cu1 | 0.55567 (5) | 0.77831 (4) | 0.23297 (2) | 0.03907 (14) | |
Cu2 | 0.250000 | 0.63912 (6) | 0.250000 | 0.03780 (18) | |
Cu3 | 0.74211 (6) | 0.71128 (5) | 0.36184 (2) | 0.04386 (15) | |
Cu4 | 0.250000 | −0.08429 (6) | 0.250000 | 0.03787 (18) | |
N1 | 1.1706 (4) | 0.2934 (3) | 0.08878 (14) | 0.0372 (8) | |
O1 | 0.5823 (3) | 0.6057 (2) | 0.21601 (11) | 0.0415 (7) | |
O2 | 0.3667 (3) | 0.5103 (2) | 0.22349 (11) | 0.0372 (7) | |
O3 | 0.3445 (3) | 0.0454 (2) | 0.21498 (11) | 0.0388 (7) | |
O4 | 0.5639 (3) | −0.0380 (2) | 0.24054 (11) | 0.0409 (7) | |
O5 | 0.9105 (3) | 0.2516 (2) | 0.16114 (11) | 0.0382 (7) | |
O6 | 0.3445 (3) | 0.7793 (2) | 0.21613 (11) | 0.0379 (7) | |
H1X | 0.305681 | 0.772498 | 0.186020 | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0431 (3) | 0.0401 (2) | 0.0495 (3) | 0.01136 (18) | −0.0140 (2) | −0.01142 (19) |
Br2 | 0.0409 (3) | 0.0503 (3) | 0.0446 (3) | −0.01324 (19) | 0.0109 (2) | −0.0137 (2) |
Br3 | 0.0422 (3) | 0.0386 (2) | 0.0483 (3) | 0.00901 (18) | 0.0109 (2) | 0.00948 (19) |
C1 | 0.033 (2) | 0.0138 (14) | 0.038 (2) | 0.0000 (11) | −0.0139 (17) | −0.0040 (13) |
C2 | 0.032 (2) | 0.0234 (14) | 0.049 (3) | 0.0034 (14) | −0.0067 (18) | 0.0106 (16) |
C3 | 0.035 (2) | 0.031 (2) | 0.047 (3) | −0.0116 (17) | 0.0105 (19) | −0.0082 (18) |
C4 | 0.038 (2) | 0.036 (2) | 0.045 (3) | −0.0121 (18) | 0.0138 (19) | −0.0112 (18) |
C5 | 0.039 (3) | 0.040 (2) | 0.041 (3) | 0.0151 (18) | 0.014 (2) | 0.0099 (18) |
C6 | 0.037 (2) | 0.032 (2) | 0.043 (3) | −0.0074 (17) | 0.0061 (19) | 0.0115 (17) |
C7 | 0.035 (2) | 0.0226 (13) | 0.050 (3) | 0.0005 (15) | 0.0138 (19) | 0.0053 (16) |
C8 | 0.037 (3) | 0.032 (2) | 0.047 (3) | −0.0095 (18) | 0.011 (2) | −0.0101 (18) |
C9 | 0.034 (2) | 0.036 (2) | 0.043 (3) | 0.0074 (17) | 0.0105 (18) | 0.0110 (17) |
C10 | 0.037 (2) | 0.042 (2) | 0.041 (3) | −0.0085 (18) | 0.0085 (19) | 0.0110 (19) |
C11 | 0.037 (2) | 0.038 (2) | 0.045 (3) | −0.0053 (16) | −0.0032 (18) | 0.0114 (18) |
C12 | 0.037 (2) | 0.035 (2) | 0.043 (3) | 0.0086 (17) | 0.0073 (19) | −0.0080 (18) |
C13 | 0.042 (3) | 0.034 (2) | 0.047 (3) | −0.0126 (19) | −0.008 (2) | −0.0108 (19) |
C14 | 0.038 (2) | 0.041 (2) | 0.043 (3) | −0.0157 (18) | 0.0075 (19) | 0.0090 (18) |
C15 | 0.044 (3) | 0.044 (3) | 0.046 (3) | −0.011 (2) | 0.013 (2) | 0.014 (2) |
C16 | 0.045 (3) | 0.036 (2) | 0.047 (3) | −0.0149 (19) | −0.010 (2) | 0.0121 (19) |
C17 | 0.036 (2) | 0.036 (2) | 0.047 (3) | 0.0090 (18) | 0.0104 (19) | 0.0114 (18) |
C18 | 0.040 (2) | 0.039 (2) | 0.042 (3) | 0.0141 (18) | 0.012 (2) | 0.0095 (18) |
C19 | 0.042 (3) | 0.036 (2) | 0.051 (3) | 0.0136 (19) | 0.009 (2) | −0.0058 (19) |
Cu1 | 0.0360 (3) | 0.0338 (3) | 0.0485 (4) | −0.0089 (2) | 0.0098 (2) | 0.0090 (2) |
Cu2 | 0.0364 (4) | 0.0332 (4) | 0.0452 (5) | 0.000 | 0.0111 (3) | 0.000 |
Cu3 | 0.0418 (3) | 0.0426 (3) | 0.0490 (4) | −0.0109 (2) | 0.0135 (3) | −0.0132 (2) |
Cu4 | 0.0366 (4) | 0.0330 (4) | 0.0453 (5) | 0.000 | 0.0103 (3) | 0.000 |
N1 | 0.0333 (19) | 0.0360 (19) | 0.042 (2) | 0.0078 (13) | 0.0054 (15) | −0.0111 (14) |
O1 | 0.0360 (17) | 0.0375 (16) | 0.053 (2) | 0.0092 (13) | 0.0136 (14) | 0.0105 (13) |
O2 | 0.0347 (16) | 0.0312 (15) | 0.0470 (19) | 0.0113 (11) | 0.0106 (13) | 0.0084 (12) |
O3 | 0.0357 (18) | 0.0330 (15) | 0.0491 (19) | −0.0079 (12) | 0.0117 (13) | −0.0084 (12) |
O4 | 0.0356 (16) | 0.0353 (16) | 0.049 (2) | −0.0100 (12) | −0.0081 (13) | 0.0123 (13) |
O5 | 0.0341 (17) | 0.0346 (15) | 0.0471 (19) | −0.0095 (12) | 0.0104 (13) | −0.0105 (12) |
O6 | 0.0347 (16) | 0.0373 (16) | 0.0423 (19) | 0.0093 (12) | 0.0077 (13) | −0.0095 (12) |
Geometric parameters (Å, º) top
Br1—Cu3 | 2.3471 (7) | C13—H13B | 0.9600 |
Br1—Cu1 | 2.8470 (8) | C13—H13C | 0.9600 |
Br2—Cu3 | 2.4627 (8) | C14—C15 | 1.506 (5) |
Br3—Cu3 | 2.3836 (7) | C14—N1 | 1.523 (5) |
C1—C2 | 1.346 (5) | C14—H14A | 0.9700 |
C1—C6 | 1.416 (5) | C14—H14B | 0.9700 |
C1—C7 | 1.510 (5) | C15—C16 | 1.525 (5) |
C2—C3 | 1.421 (5) | C15—H15A | 0.9700 |
C2—H2 | 0.9300 | C15—H15B | 0.9700 |
C3—C4 | 1.379 (6) | C16—H16A | 0.9600 |
C3—C8 | 1.502 (5) | C16—H16B | 0.9600 |
C4—C5 | 1.406 (5) | C16—H16C | 0.9600 |
C4—H4 | 0.9300 | C17—N1 | 1.499 (5) |
C5—C6 | 1.344 (5) | C17—C18 | 1.506 (6) |
C5—O5 | 1.395 (5) | C17—H17A | 0.9700 |
C6—H6 | 0.9300 | C17—H17B | 0.9700 |
C7—O1 | 1.252 (4) | C18—C19 | 1.546 (5) |
C7—O2 | 1.249 (4) | C18—H18A | 0.9700 |
C8—O3 | 1.254 (5) | C18—H18B | 0.9700 |
C8—O4 | 1.264 (5) | C19—H19A | 0.9600 |
C9—O5 | 1.419 (4) | C19—H19B | 0.9600 |
C9—C10 | 1.497 (5) | C19—H19C | 0.9600 |
C9—H9A | 0.9700 | Cu1—O1 | 1.919 (3) |
C9—H9B | 0.9700 | Cu1—O6 | 1.923 (3) |
C10—N1 | 1.537 (5) | Cu1—O4i | 1.972 (3) |
C10—H10A | 0.9700 | Cu2—O2ii | 1.912 (3) |
C10—H10B | 0.9700 | Cu2—O2 | 1.912 (3) |
C11—C12 | 1.529 (5) | Cu2—O6ii | 1.985 (3) |
C11—N1 | 1.535 (5) | Cu2—O6 | 1.985 (3) |
C11—H11A | 0.9700 | Cu2—Cu4i | 2.9531 (10) |
C11—H11B | 0.9700 | Cu4—O3ii | 1.919 (3) |
C12—C13 | 1.541 (5) | Cu4—O3 | 1.919 (3) |
C12—H12A | 0.9700 | Cu4—O6iii | 1.955 (2) |
C12—H12B | 0.9700 | Cu4—O6iv | 1.955 (2) |
C13—H13A | 0.9600 | O6—H1X | 0.8501 |
| | | |
Cu3—Br1—Cu1 | 92.19 (2) | H16A—C16—H16B | 109.5 |
C2—C1—C6 | 120.4 (3) | C15—C16—H16C | 109.5 |
C2—C1—C7 | 118.7 (4) | H16A—C16—H16C | 109.5 |
C6—C1—C7 | 120.7 (3) | H16B—C16—H16C | 109.5 |
C1—C2—C3 | 119.2 (4) | N1—C17—C18 | 114.4 (4) |
C1—C2—H2 | 120.4 | N1—C17—H17A | 108.7 |
C3—C2—H2 | 120.4 | C18—C17—H17A | 108.7 |
C4—C3—C2 | 121.5 (4) | N1—C17—H17B | 108.7 |
C4—C3—C8 | 120.2 (4) | C18—C17—H17B | 108.7 |
C2—C3—C8 | 117.7 (4) | H17A—C17—H17B | 107.6 |
C3—C4—C5 | 116.6 (4) | C17—C18—C19 | 108.5 (4) |
C3—C4—H4 | 121.7 | C17—C18—H18A | 110.0 |
C5—C4—H4 | 121.7 | C19—C18—H18A | 110.0 |
C6—C5—O5 | 124.1 (4) | C17—C18—H18B | 110.0 |
C6—C5—C4 | 123.0 (4) | C19—C18—H18B | 110.0 |
O5—C5—C4 | 112.9 (3) | H18A—C18—H18B | 108.4 |
C5—C6—C1 | 119.2 (3) | C18—C19—H19A | 109.5 |
C5—C6—H6 | 120.4 | C18—C19—H19B | 109.5 |
C1—C6—H6 | 120.4 | H19A—C19—H19B | 109.5 |
O1—C7—O2 | 126.0 (4) | C18—C19—H19C | 109.5 |
O1—C7—C1 | 117.1 (3) | H19A—C19—H19C | 109.5 |
O2—C7—C1 | 116.7 (3) | H19B—C19—H19C | 109.5 |
O3—C8—O4 | 124.2 (4) | O1—Cu1—O6 | 95.42 (11) |
O3—C8—C3 | 118.6 (4) | O1—Cu1—O4i | 167.18 (12) |
O4—C8—C3 | 117.1 (4) | O6—Cu1—O4i | 92.61 (10) |
O5—C9—C10 | 107.6 (3) | O1—Cu1—Br1 | 89.89 (9) |
O5—C9—H9A | 110.2 | O6—Cu1—Br1 | 85.89 (9) |
C10—C9—H9A | 110.2 | O4i—Cu1—Br1 | 100.67 (9) |
O5—C9—H9B | 110.2 | O2ii—Cu2—O2 | 87.98 (16) |
C10—C9—H9B | 110.2 | O2ii—Cu2—O6ii | 95.48 (10) |
H9A—C9—H9B | 108.5 | O2—Cu2—O6ii | 171.62 (11) |
C9—C10—N1 | 116.4 (3) | O2ii—Cu2—O6 | 171.62 (11) |
C9—C10—H10A | 108.2 | O2—Cu2—O6 | 95.48 (10) |
N1—C10—H10A | 108.2 | O6ii—Cu2—O6 | 82.15 (14) |
C9—C10—H10B | 108.2 | O2ii—Cu2—Cu4i | 136.01 (8) |
N1—C10—H10B | 108.2 | O2—Cu2—Cu4i | 136.01 (8) |
H10A—C10—H10B | 107.3 | O6ii—Cu2—Cu4i | 41.07 (7) |
C12—C11—N1 | 112.1 (3) | O6—Cu2—Cu4i | 41.07 (7) |
C12—C11—H11A | 109.2 | Br1—Cu3—Br3 | 143.20 (3) |
N1—C11—H11A | 109.2 | Br1—Cu3—Br2 | 105.27 (2) |
C12—C11—H11B | 109.2 | Br3—Cu3—Br2 | 105.88 (3) |
N1—C11—H11B | 109.2 | O3ii—Cu4—O3 | 87.57 (16) |
H11A—C11—H11B | 107.9 | O3ii—Cu4—O6iii | 177.97 (12) |
C11—C12—C13 | 107.0 (3) | O3—Cu4—O6iii | 94.38 (11) |
C11—C12—H12A | 110.3 | O3ii—Cu4—O6iv | 94.38 (11) |
C13—C12—H12A | 110.3 | O3—Cu4—O6iv | 177.97 (12) |
C11—C12—H12B | 110.3 | O6iii—Cu4—O6iv | 83.68 (16) |
C13—C12—H12B | 110.3 | O3ii—Cu4—Cu2iii | 136.21 (8) |
H12A—C12—H12B | 108.6 | O3—Cu4—Cu2iii | 136.21 (8) |
C12—C13—H13A | 109.5 | O6iii—Cu4—Cu2iii | 41.84 (8) |
C12—C13—H13B | 109.5 | O6iv—Cu4—Cu2iii | 41.84 (8) |
H13A—C13—H13B | 109.5 | C17—N1—C10 | 106.5 (3) |
C12—C13—H13C | 109.5 | C17—N1—C14 | 111.5 (3) |
H13A—C13—H13C | 109.5 | C10—N1—C14 | 107.6 (3) |
H13B—C13—H13C | 109.5 | C17—N1—C11 | 113.1 (3) |
C15—C14—N1 | 116.4 (3) | C10—N1—C11 | 110.2 (3) |
C15—C14—H14A | 108.2 | C14—N1—C11 | 107.9 (3) |
N1—C14—H14A | 108.2 | C7—O1—Cu1 | 133.6 (3) |
C15—C14—H14B | 108.2 | C7—O2—Cu2 | 129.9 (3) |
N1—C14—H14B | 108.2 | C8—O3—Cu4 | 116.9 (3) |
H14A—C14—H14B | 107.3 | C8—O4—Cu1iii | 131.7 (3) |
C14—C15—C16 | 108.5 (4) | C5—O5—C9 | 118.1 (3) |
C14—C15—H15A | 110.0 | Cu1—O6—Cu4i | 111.42 (13) |
C16—C15—H15A | 110.0 | Cu1—O6—Cu2 | 110.59 (13) |
C14—C15—H15B | 110.0 | Cu4i—O6—Cu2 | 97.09 (12) |
C16—C15—H15B | 110.0 | Cu1—O6—H1X | 122.2 |
H15A—C15—H15B | 108.4 | Cu4i—O6—H1X | 110.1 |
C15—C16—H16A | 109.5 | Cu2—O6—H1X | 102.2 |
C15—C16—H16B | 109.5 | | |
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y, −z+1/2; (iii) x, y−1, z; (iv) −x+1/2, y−1, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Br2v | 0.93 | 3.05 | 3.555 (4) | 116 |
C9—H9B···Br2v | 0.97 | 2.85 | 3.767 (4) | 157 |
C14—H14B···Br2v | 0.97 | 3.10 | 4.066 (4) | 173 |
C10—H10B···O2vi | 0.97 | 2.53 | 3.449 (5) | 157 |
C11—H11A···O5 | 0.97 | 2.52 | 3.023 (6) | 112 |
C12—H12A···O5 | 0.97 | 2.62 | 3.161 (5) | 116 |
C14—H14A···Br2vii | 0.97 | 2.99 | 3.875 (4) | 153 |
C18—H18A···Br2vii | 0.97 | 2.92 | 3.860 (4) | 164 |
O6—H1X···Br1ii | 0.85 | 2.77 | 3.269 (3) | 119 |
C6—H6···Br2v | 0.93 | 3.05 | 3.555 (4) | 116 |
C9—H9B···Br2v | 0.97 | 2.85 | 3.767 (4) | 157 |
C10—H10B···O2vi | 0.97 | 2.53 | 3.449 (5) | 157 |
C11—H11A···O5 | 0.97 | 2.52 | 3.023 (6) | 112 |
C12—H12A···O5 | 0.97 | 2.62 | 3.161 (5) | 116 |
C14—H14A···Br2vii | 0.97 | 2.99 | 3.875 (4) | 153 |
C14—H14B···Br2v | 0.97 | 3.10 | 4.066 (4) | 173 |
C18—H18A···Br2vii | 0.97 | 2.92 | 3.860 (4) | 164 |
O6—H1X···Br1ii | 0.85 | 2.77 | 3.269 (3) | 119 |
Symmetry codes: (ii) −x+1/2, y, −z+1/2; (v) −x+3/2, y, −z+1/2; (vi) x+1, y, z; (vii) x+1/2, −y+1, z−1/2. |
Poly[bromido{µ
3-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}zinc(II)] (3)
top
Crystal data top
[ZnBr(C19H28NO5)] | F(000) = 1016 |
Mr = 495.70 | Dx = 1.580 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5479 (7) Å | Cell parameters from 9963 reflections |
b = 14.7949 (10) Å | θ = 2.2–34.2° |
c = 12.3782 (9) Å | µ = 3.13 mm−1 |
β = 99.813 (2)° | T = 290 K |
V = 2083.9 (2) Å3 | Prism, colorless |
Z = 4 | 0.35 × 0.26 × 0.21 mm |
Data collection top
Bruker D8 diffractometer | 3523 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
phi and ω scans | θmax = 25.8°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −14→12 |
Tmin = 0.418, Tmax = 0.747 | k = −18→15 |
14849 measured reflections | l = −15→15 |
3966 independent 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0492P)2 + 2.801P] where P = (Fo2 + 2Fc2)/3 |
3966 reflections | (Δ/σ)max = 0.001 |
247 parameters | Δρmax = 0.72 e Å−3 |
5 restraints | Δρmin = −1.25 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O5 | 0.62771 (16) | 0.03422 (12) | 0.54057 (16) | 0.0263 (4) | |
C1 | 0.7629 (2) | −0.05002 (17) | 0.6674 (2) | 0.0224 (5) | |
N1 | 1.16840 (19) | 0.24469 (15) | 0.80952 (19) | 0.0247 (5) | |
C2 | 0.8204 (2) | 0.02892 (17) | 0.7077 (2) | 0.0230 (5) | |
H2 | 0.793506 | 0.084924 | 0.679920 | 0.028* | |
C3 | 0.8987 (3) | −0.13799 (19) | 0.7940 (2) | 0.0290 (6) | |
C9 | 0.9577 (2) | 0.18023 (19) | 0.7768 (3) | 0.0315 (6) | |
H9A | 0.877783 | 0.198673 | 0.780298 | 0.038* | |
H9B | 0.964954 | 0.173597 | 0.700304 | 0.038* | |
C10 | 1.0425 (2) | 0.25082 (19) | 0.8300 (3) | 0.0298 (6) | |
H10A | 1.044118 | 0.248118 | 0.908518 | 0.036* | |
H10B | 1.011841 | 0.309683 | 0.805254 | 0.036* | |
C4 | 0.8014 (2) | −0.13318 (18) | 0.7113 (2) | 0.0275 (6) | |
H4 | 0.761982 | −0.185707 | 0.685258 | 0.033* | |
O1 | 0.98248 (19) | 0.09652 (14) | 0.83219 (19) | 0.0374 (5) | |
C5 | 0.9578 (2) | −0.0601 (2) | 0.8324 (2) | 0.0298 (6) | |
H5 | 1.023901 | −0.063376 | 0.886931 | 0.036* | |
C6 | 0.6606 (2) | −0.04292 (18) | 0.5756 (2) | 0.0253 (6) | |
C16 | 1.2301 (2) | 0.1595 (2) | 0.8580 (2) | 0.0310 (6) | |
H16A | 1.188629 | 0.107773 | 0.821950 | 0.037* | |
H16B | 1.308733 | 0.158960 | 0.840231 | 0.037* | |
C7 | 0.9178 (2) | 0.02309 (18) | 0.7891 (2) | 0.0262 (6) | |
C11 | 1.1752 (3) | 0.2412 (2) | 0.6878 (2) | 0.0314 (6) | |
H11A | 1.257539 | 0.239072 | 0.680621 | 0.038* | |
H11B | 1.139721 | 0.184978 | 0.658536 | 0.038* | |
C13 | 1.2276 (2) | 0.3291 (2) | 0.8635 (3) | 0.0313 (6) | |
H13A | 1.184349 | 0.381604 | 0.831575 | 0.038* | |
H13B | 1.221987 | 0.327893 | 0.940759 | 0.038* | |
C12 | 1.1184 (4) | 0.3172 (3) | 0.6173 (3) | 0.0492 (9) | |
H12A | 1.151002 | 0.374520 | 0.645730 | 0.059* | |
H12B | 1.034542 | 0.317846 | 0.618245 | 0.059* | |
C8 | 0.9435 (3) | −0.2274 (2) | 0.8428 (3) | 0.0431 (7) | |
C14 | 1.3551 (3) | 0.3409 (3) | 0.8532 (3) | 0.0528 (10) | |
H14A | 1.362331 | 0.345540 | 0.776457 | 0.063* | |
H14B | 1.399997 | 0.288818 | 0.884093 | 0.063* | |
C17 | 1.2403 (4) | 0.1467 (3) | 0.9802 (3) | 0.0499 (9) | |
H17A | 1.162833 | 0.149449 | 1.000526 | 0.060* | |
H17B | 1.287675 | 0.194831 | 1.018348 | 0.060* | |
C15 | 1.4028 (4) | 0.4256 (3) | 0.9134 (4) | 0.0717 (14) | |
H15A | 1.358855 | 0.477058 | 0.881770 | 0.108* | |
H15B | 1.483990 | 0.432983 | 0.907311 | 0.108* | |
H15C | 1.395652 | 0.420603 | 0.989319 | 0.108* | |
C18 | 1.2962 (4) | 0.0564 (3) | 1.0132 (4) | 0.0634 (11) | |
H18A | 1.305587 | 0.049750 | 1.091343 | 0.095* | |
H18B | 1.371736 | 0.053264 | 0.990847 | 0.095* | |
H18C | 1.246893 | 0.008879 | 0.978367 | 0.095* | |
O4 | 0.61517 (19) | −0.11582 (13) | 0.53639 (19) | 0.0377 (5) | |
O2 | 0.8730 (3) | −0.29053 (16) | 0.8422 (3) | 0.0667 (8) | |
O3 | 1.0481 (3) | −0.2357 (2) | 0.8837 (3) | 0.0687 (8) | |
C20 | 1.1399 (4) | 0.3041 (3) | 0.5013 (3) | 0.0626 (11) | |
H20A | 1.222957 | 0.304751 | 0.500619 | 0.094* | |
H20B | 1.102976 | 0.352185 | 0.455846 | 0.094* | |
H20C | 1.107624 | 0.247248 | 0.473613 | 0.094* | |
Zn1 | 0.99387 (3) | −0.38971 (2) | 0.90243 (3) | 0.02677 (11) | |
Br1 | 1.04286 (3) | −0.46593 (2) | 0.74963 (3) | 0.04755 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0294 (10) | 0.0213 (10) | 0.0277 (10) | −0.0009 (7) | 0.0030 (8) | 0.0000 (8) |
C1 | 0.0248 (12) | 0.0177 (12) | 0.0256 (13) | −0.0010 (10) | 0.0065 (10) | −0.0013 (10) |
N1 | 0.0237 (11) | 0.0200 (11) | 0.0308 (12) | −0.0006 (9) | 0.0054 (9) | −0.0061 (9) |
C2 | 0.0246 (12) | 0.0143 (12) | 0.0291 (14) | 0.0004 (9) | 0.0023 (10) | 0.0027 (10) |
C3 | 0.0367 (15) | 0.0191 (13) | 0.0341 (15) | 0.0079 (11) | 0.0147 (12) | 0.0092 (11) |
C9 | 0.0235 (13) | 0.0201 (13) | 0.0485 (18) | 0.0001 (10) | −0.0010 (12) | 0.0001 (12) |
C10 | 0.0237 (13) | 0.0221 (13) | 0.0445 (17) | 0.0008 (11) | 0.0081 (11) | −0.0074 (12) |
C4 | 0.0350 (14) | 0.0158 (12) | 0.0342 (15) | −0.0020 (10) | 0.0127 (11) | 0.0002 (11) |
O1 | 0.0366 (11) | 0.0248 (10) | 0.0441 (13) | −0.0085 (9) | −0.0126 (9) | 0.0053 (9) |
C5 | 0.0294 (14) | 0.0286 (15) | 0.0306 (15) | 0.0047 (11) | 0.0027 (11) | 0.0083 (12) |
C6 | 0.0266 (13) | 0.0217 (13) | 0.0285 (14) | −0.0042 (10) | 0.0072 (10) | −0.0030 (11) |
C16 | 0.0296 (14) | 0.0279 (15) | 0.0357 (16) | 0.0075 (11) | 0.0060 (11) | −0.0017 (12) |
C7 | 0.0263 (13) | 0.0199 (13) | 0.0320 (15) | −0.0030 (10) | 0.0041 (11) | 0.0026 (11) |
C11 | 0.0365 (15) | 0.0295 (15) | 0.0284 (15) | 0.0004 (12) | 0.0062 (11) | −0.0080 (12) |
C13 | 0.0323 (15) | 0.0255 (14) | 0.0364 (16) | −0.0085 (11) | 0.0068 (11) | −0.0117 (12) |
C12 | 0.067 (2) | 0.041 (2) | 0.0386 (19) | 0.0067 (17) | 0.0059 (16) | 0.0017 (16) |
C8 | 0.0668 (14) | 0.0275 (10) | 0.0411 (18) | 0.0218 (10) | 0.0265 (13) | 0.0155 (13) |
C14 | 0.0371 (18) | 0.061 (2) | 0.062 (2) | −0.0222 (17) | 0.0148 (16) | −0.025 (2) |
C17 | 0.063 (2) | 0.051 (2) | 0.0360 (18) | 0.0173 (18) | 0.0098 (16) | 0.0031 (16) |
C15 | 0.064 (3) | 0.085 (3) | 0.071 (3) | −0.049 (2) | 0.024 (2) | −0.038 (3) |
C18 | 0.073 (3) | 0.066 (3) | 0.051 (2) | 0.026 (2) | 0.011 (2) | 0.021 (2) |
O4 | 0.0424 (12) | 0.0218 (10) | 0.0437 (13) | −0.0059 (9) | −0.0073 (9) | −0.0079 (9) |
O2 | 0.0800 (14) | 0.0218 (11) | 0.108 (2) | 0.0239 (8) | 0.0427 (15) | 0.0301 (13) |
O3 | 0.0838 (14) | 0.0480 (16) | 0.0660 (18) | 0.0312 (12) | −0.0107 (15) | 0.0171 (14) |
C20 | 0.084 (3) | 0.065 (3) | 0.0353 (19) | 0.000 (2) | 0.0013 (18) | 0.0042 (19) |
Zn1 | 0.03115 (18) | 0.01738 (17) | 0.0312 (2) | 0.00365 (12) | 0.00376 (13) | 0.00360 (12) |
Br1 | 0.0651 (2) | 0.0404 (2) | 0.0419 (2) | 0.00433 (16) | 0.02288 (16) | −0.00023 (14) |
Geometric parameters (Å, º) top
Br1—Zn1 | 2.3523 (5) | C10—H10A | 0.9700 |
Zn1—O2 | 2.075 (2) | C10—H10B | 0.9700 |
Zn1—O3 | 2.385 (3) | C11—H11A | 0.9700 |
Zn1—O4i | 1.982 (2) | C11—H11B | 0.9700 |
Zn1—O5ii | 2.0182 (19) | C11—C12 | 1.504 (5) |
Zn1—C8 | 2.551 (3) | C12—H12A | 0.9700 |
O1—C7 | 1.374 (3) | C12—H12B | 0.9700 |
O1—C9 | 1.421 (3) | C12—C20 | 1.512 (5) |
O2—C8 | 1.239 (5) | C13—H13A | 0.9700 |
O3—C8 | 1.234 (5) | C13—H13B | 0.9700 |
O4—C6 | 1.260 (3) | C13—C14 | 1.509 (4) |
O5—C6 | 1.256 (3) | C14—H14A | 0.9700 |
N1—C10 | 1.520 (3) | C14—H14B | 0.9700 |
N1—C11 | 1.523 (4) | C14—C15 | 1.513 (5) |
N1—C13 | 1.523 (3) | C15—H15A | 0.9600 |
N1—C16 | 1.521 (4) | C15—H15B | 0.9600 |
C1—C2 | 1.393 (4) | C15—H15C | 0.9600 |
C1—C4 | 1.387 (4) | C16—H16A | 0.9700 |
C1—C6 | 1.496 (4) | C16—H16B | 0.9700 |
C2—H2 | 0.9300 | C16—C17 | 1.509 (5) |
C2—C7 | 1.379 (4) | C17—H17A | 0.9700 |
C3—C4 | 1.387 (4) | C17—H17B | 0.9700 |
C3—C5 | 1.381 (4) | C17—C18 | 1.510 (5) |
C3—C8 | 1.508 (4) | C18—H18A | 0.9600 |
C4—H4 | 0.9300 | C18—H18B | 0.9600 |
C5—H5 | 0.9300 | C18—H18C | 0.9600 |
C5—C7 | 1.390 (4) | C20—H20A | 0.9600 |
C9—H9A | 0.9700 | C20—H20B | 0.9600 |
C9—H9B | 0.9700 | C20—H20C | 0.9600 |
C9—C10 | 1.505 (4) | | |
| | | |
Br1—Zn1—O3 | 106.07 (8) | N1—C10—H10B | 108.0 |
Br1—Zn1—C8 | 107.03 (8) | C9—C10—N1 | 117.1 (2) |
O2—Zn1—Br1 | 106.82 (10) | C9—C10—H10A | 108.0 |
O2—Zn1—O3 | 57.39 (11) | C9—C10—H10B | 108.0 |
O2—Zn1—C8 | 28.79 (12) | H10A—C10—H10B | 107.3 |
O3—Zn1—C8 | 28.71 (11) | N1—C11—H11A | 108.0 |
O4i—Zn1—Br1 | 117.39 (7) | N1—C11—H11B | 108.0 |
O4i—Zn1—O2 | 127.45 (12) | H11A—C11—H11B | 107.2 |
O4i—Zn1—O3 | 83.21 (9) | C12—C11—N1 | 117.2 (3) |
O4i—Zn1—O5ii | 99.50 (9) | C12—C11—H11A | 108.0 |
O4i—Zn1—C8 | 107.28 (11) | C12—C11—H11B | 108.0 |
O5ii—Zn1—Br1 | 106.91 (6) | C11—C12—H12A | 109.8 |
O5ii—Zn1—O2 | 93.12 (10) | C11—C12—H12B | 109.8 |
O5ii—Zn1—O3 | 140.95 (10) | C11—C12—C20 | 109.3 (3) |
O5ii—Zn1—C8 | 119.23 (10) | H12A—C12—H12B | 108.3 |
C7—O1—C9 | 116.8 (2) | C20—C12—H12A | 109.8 |
C8—O2—Zn1 | 97.5 (2) | C20—C12—H12B | 109.8 |
C8—O3—Zn1 | 83.1 (2) | N1—C13—H13A | 108.4 |
C6—O4—Zn1iii | 118.39 (19) | N1—C13—H13B | 108.4 |
C6—O5—Zn1iv | 124.98 (18) | H13A—C13—H13B | 107.5 |
C10—N1—C11 | 112.3 (2) | C14—C13—N1 | 115.4 (2) |
C10—N1—C13 | 104.4 (2) | C14—C13—H13A | 108.4 |
C10—N1—C16 | 112.4 (2) | C14—C13—H13B | 108.4 |
C11—N1—C13 | 111.5 (2) | C13—C14—H14A | 109.8 |
C16—N1—C11 | 105.2 (2) | C13—C14—H14B | 109.8 |
C16—N1—C13 | 111.2 (2) | C13—C14—C15 | 109.4 (3) |
C2—C1—C6 | 118.7 (2) | H14A—C14—H14B | 108.2 |
C4—C1—C2 | 120.1 (2) | C15—C14—H14A | 109.8 |
C4—C1—C6 | 121.2 (2) | C15—C14—H14B | 109.8 |
C1—C2—H2 | 120.4 | C14—C15—H15A | 109.5 |
C7—C2—C1 | 119.3 (2) | C14—C15—H15B | 109.5 |
C7—C2—H2 | 120.4 | C14—C15—H15C | 109.5 |
C4—C3—C8 | 121.3 (3) | H15A—C15—H15B | 109.5 |
C5—C3—C4 | 120.1 (2) | H15A—C15—H15C | 109.5 |
C5—C3—C8 | 118.5 (3) | H15B—C15—H15C | 109.5 |
C1—C4—H4 | 120.0 | N1—C16—H16A | 108.1 |
C3—C4—C1 | 120.0 (3) | N1—C16—H16B | 108.1 |
C3—C4—H4 | 120.0 | H16A—C16—H16B | 107.3 |
C3—C5—H5 | 120.2 | C17—C16—N1 | 116.8 (2) |
C3—C5—C7 | 119.6 (3) | C17—C16—H16A | 108.1 |
C7—C5—H5 | 120.2 | C17—C16—H16B | 108.1 |
O4—C6—C1 | 117.1 (2) | C16—C17—H17A | 109.7 |
O5—C6—O4 | 124.3 (3) | C16—C17—H17B | 109.7 |
O5—C6—C1 | 118.6 (2) | C16—C17—C18 | 109.8 (3) |
O1—C7—C2 | 123.8 (2) | H17A—C17—H17B | 108.2 |
O1—C7—C5 | 115.3 (2) | C18—C17—H17A | 109.7 |
C2—C7—C5 | 120.9 (3) | C18—C17—H17B | 109.7 |
O2—C8—Zn1 | 53.74 (17) | C17—C18—H18A | 109.5 |
O2—C8—C3 | 118.6 (3) | C17—C18—H18B | 109.5 |
O3—C8—Zn1 | 68.14 (19) | C17—C18—H18C | 109.5 |
O3—C8—O2 | 121.6 (3) | H18A—C18—H18B | 109.5 |
O3—C8—C3 | 119.8 (3) | H18A—C18—H18C | 109.5 |
C3—C8—Zn1 | 170.9 (3) | H18B—C18—H18C | 109.5 |
O1—C9—H9A | 109.8 | C12—C20—H20A | 109.5 |
O1—C9—H9B | 109.8 | C12—C20—H20B | 109.5 |
O1—C9—C10 | 109.3 (2) | C12—C20—H20C | 109.5 |
H9A—C9—H9B | 108.3 | H20A—C20—H20B | 109.5 |
C10—C9—H9A | 109.8 | H20A—C20—H20C | 109.5 |
C10—C9—H9B | 109.8 | H20B—C20—H20C | 109.5 |
N1—C10—H10A | 108.0 | | |
Symmetry codes: (i) x+1/2, −y−1/2, z+1/2; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x−1/2, −y−1/2, z−1/2; (iv) −x+3/2, y+1/2, −z+3/2. |
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