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In the title Schiff base tetranuclear copper(II) complex, two discrete environments are present in the structure: CuN2OBr2 and CuBr4. Two copper(II) cations are situated in distorted square-based pyramidal environment, while two copper(II) cations are located in distorted tetrahedral geometry.
Keywords: crystal structure; acetylpyridine; 2-aminoethanol; 2-(1-((2-hyroxyethyl)imino)acetylpyridine); square pyramidal; tetrahedral.
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023011040/ex2076sup1.cif |
CCDC reference: 2321970
Computing details top
Poly[hexa-µ-bromido-bis{2-[1-(pyridin-2-yl)ethylideneamino]ethanolato}\
tetracopper(II)] top
Crystal data top
[Cu4Br6(C9H11N2O)2] | F(000) = 2004 |
Mr = 1060 | Dx = 2.551 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 23.1656 (12) Å | Cell parameters from 8413 reflections |
b = 7.7041 (3) Å | θ = 2.6–28.6° |
c = 16.5664 (8) Å | µ = 11.74 mm−1 |
β = 110.896 (6)° | T = 292 K |
V = 2762.1 (2) Å3 | Block, metallic greenish green |
Z = 4 | 0.2 × 0.2 × 0.1 mm |
Data collection top
XtaLAB AFC12 (RINC): Kappa single diffractometer | 4912 reflections with I > 2σ(I) |
Detector resolution: 5.8140 pixels mm-1 | Rint = 0.056 |
ω scans | θmax = 26.0°, θmin = 2.5° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −28→28 |
Tmin = 0.479, Tmax = 1.000 | k = −9→9 |
40718 measured reflections | l = −20→20 |
5446 independent reflections |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0406P)2 + 3.9895P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5446 reflections | Δρmax = 0.95 e Å−3 |
344 parameters | Δρmin = −0.97 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br2 | 0.87911 (3) | −0.06317 (11) | 0.75247 (5) | 0.03317 (18) | 0.942 (2) |
Br1 | 0.88670 (3) | 0.43944 (11) | 0.74718 (4) | 0.03271 (18) | 0.942 (2) |
Br4 | 0.75698 (3) | 0.22558 (9) | 0.56292 (4) | 0.03737 (17) | |
Br3 | 0.74379 (3) | 0.24099 (10) | 0.80563 (5) | 0.03751 (17) | |
Cu1 | 0.88539 (3) | 0.65639 (9) | 0.84828 (4) | 0.02455 (19) | 0.942 (2) |
Br6 | 0.61671 (5) | 1.04176 (13) | 0.36210 (6) | 0.0314 (2) | 0.927 (3) |
Br5 | 0.62288 (6) | 0.54630 (11) | 0.37724 (8) | 0.0332 (3) | 0.927 (3) |
Cu3 | 0.81423 (4) | 0.18899 (12) | 0.73163 (7) | 0.0435 (3) | 0.942 (2) |
Cu2 | 0.61485 (3) | 0.82568 (9) | 0.46447 (5) | 0.0242 (3) | 0.927 (3) |
Cu4 | 0.68932 (4) | 0.29613 (14) | 0.41925 (6) | 0.0428 (2) | 0.94 |
O1 | 0.79475 (19) | 0.6363 (6) | 0.8272 (3) | 0.0420 (10) | |
H1 | 0.779586 | 0.539265 | 0.824191 | 0.063* | |
N4 | 0.6105 (3) | 0.7513 (7) | 0.5758 (3) | 0.0334 (12) | |
C5 | 0.9925 (4) | 0.7463 (9) | 0.9904 (5) | 0.0432 (8) | |
N2 | 0.8871 (3) | 0.7459 (7) | 0.9601 (3) | 0.0313 (11) | |
N1 | 0.9763 (2) | 0.6809 (6) | 0.9083 (3) | 0.0265 (10) | |
O2 | 0.7056 (2) | 0.8353 (6) | 0.5357 (3) | 0.0429 (11) | |
H2 | 0.723439 | 0.928382 | 0.550139 | 0.064* | |
N3 | 0.5234 (2) | 0.8094 (6) | 0.4310 (3) | 0.0276 (10) | |
C14 | 0.5054 (3) | 0.7543 (6) | 0.4956 (4) | 0.0186 (10) | |
C15 | 0.5566 (3) | 0.7292 (7) | 0.5798 (4) | 0.0297 (13) | |
C4 | 1.0527 (3) | 0.7781 (9) | 1.0393 (5) | 0.0428 (9) | |
H4 | 1.063117 | 0.821780 | 1.095059 | 0.051* | |
C3 | 1.0989 (3) | 0.7447 (9) | 1.0053 (5) | 0.0433 (18) | |
H3 | 1.140193 | 0.765954 | 1.038035 | 0.052* | |
C13 | 0.4433 (3) | 0.7302 (9) | 0.4831 (4) | 0.0357 (14) | |
H13 | 0.431362 | 0.697402 | 0.528913 | 0.043* | |
C12 | 0.3997 (3) | 0.7558 (9) | 0.4020 (5) | 0.0370 (16) | |
H12 | 0.358158 | 0.735100 | 0.391713 | 0.044* | |
C1 | 1.0208 (3) | 0.6488 (8) | 0.8764 (4) | 0.0343 (13) | |
H1A | 1.009791 | 0.603748 | 0.820813 | 0.041* | |
C6 | 0.9388 (3) | 0.7732 (8) | 1.0175 (4) | 0.0327 (14) | |
C17 | 0.6690 (3) | 0.7424 (10) | 0.6488 (5) | 0.0432 (8) | |
H17A | 0.669363 | 0.643175 | 0.685041 | 0.052* | |
H17B | 0.675167 | 0.846878 | 0.683591 | 0.052* | |
C8 | 0.8269 (3) | 0.7520 (10) | 0.9717 (5) | 0.0428 (9) | |
H8A | 0.823678 | 0.655889 | 1.007648 | 0.051* | |
H8B | 0.823301 | 0.859334 | 1.000096 | 0.051* | |
C11 | 0.4180 (3) | 0.8116 (8) | 0.3370 (4) | 0.0382 (14) | |
H11 | 0.388755 | 0.832008 | 0.282335 | 0.046* | |
C9 | 0.7776 (4) | 0.7413 (12) | 0.8876 (7) | 0.065 (2) | |
H9 | 0.739468 | 0.795640 | 0.874160 | 0.078* | |
C2 | 1.0825 (3) | 0.6800 (9) | 0.9228 (5) | 0.0428 (9) | |
H2A | 1.112396 | 0.657735 | 0.898744 | 0.051* | |
C18 | 0.7190 (3) | 0.7249 (10) | 0.6106 (5) | 0.0432 (8) | |
H18A | 0.758582 | 0.757213 | 0.653413 | 0.052* | |
H18B | 0.721657 | 0.605151 | 0.594195 | 0.052* | |
C7 | 0.9505 (3) | 0.8288 (9) | 1.1081 (4) | 0.0432 (8) | |
H7A | 0.994219 | 0.840791 | 1.138423 | 0.065* | |
H7B | 0.934353 | 0.743263 | 1.136518 | 0.065* | |
H7C | 0.930618 | 0.938153 | 1.107883 | 0.065* | |
C10 | 0.4802 (3) | 0.8381 (8) | 0.3522 (4) | 0.0339 (13) | |
H10 | 0.492326 | 0.876321 | 0.307443 | 0.041* | |
C16 | 0.5438 (4) | 0.6878 (10) | 0.6593 (4) | 0.0495 (18) | |
H16A | 0.582073 | 0.671873 | 0.706658 | 0.074* | |
H16B | 0.519781 | 0.583169 | 0.650470 | 0.074* | |
H16C | 0.521134 | 0.781528 | 0.672180 | 0.074* | |
Cu1A | 0.8866 (8) | 0.837 (2) | 0.8496 (12) | 0.052 (5) | 0.058 (2) |
Br1A | 0.8769 (7) | 0.549 (3) | 0.7560 (10) | 0.059 (4) | 0.058 (2) |
Cu3A | 0.8077 (7) | 0.305 (2) | 0.7280 (11) | 0.0435 (3) | 0.058 (2) |
Br2A | 0.8834 (8) | 0.043 (3) | 0.7447 (9) | 0.059 (5) | 0.058 (2) |
Br6A | 0.6204 (8) | 0.962 (3) | 0.3729 (11) | 0.056 (4) | 0.073 (3) |
Cu2A | 0.6147 (8) | 0.6632 (17) | 0.4634 (10) | 0.062 (5) | 0.073 (3) |
Br5A | 0.6162 (9) | 0.474 (3) | 0.3627 (10) | 0.063 (5) | 0.073 (3) |
Cu4A | 0.6888 (7) | 0.190 (2) | 0.4192 (10) | 0.0428 (2) | 0.06 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br2 | 0.0374 (4) | 0.0225 (3) | 0.0403 (4) | 0.0038 (3) | 0.0146 (3) | 0.0071 (3) |
Br1 | 0.0417 (4) | 0.0279 (4) | 0.0331 (4) | −0.0146 (3) | 0.0190 (3) | −0.0105 (3) |
Br4 | 0.0293 (3) | 0.0509 (4) | 0.0253 (3) | −0.0027 (2) | 0.0017 (3) | −0.0008 (2) |
Br3 | 0.0309 (3) | 0.0501 (4) | 0.0380 (4) | −0.0067 (3) | 0.0201 (3) | −0.0033 (3) |
Cu1 | 0.0204 (4) | 0.0282 (4) | 0.0253 (4) | −0.0026 (3) | 0.0084 (3) | −0.0037 (3) |
Br6 | 0.0388 (4) | 0.0259 (4) | 0.0267 (4) | −0.0118 (4) | 0.0084 (3) | 0.0015 (4) |
Br5 | 0.0387 (5) | 0.0225 (4) | 0.0389 (5) | 0.0045 (3) | 0.0143 (4) | −0.0040 (3) |
Cu3 | 0.0419 (5) | 0.0373 (5) | 0.0589 (6) | 0.0010 (4) | 0.0271 (5) | −0.0042 (4) |
Cu2 | 0.0202 (4) | 0.0300 (4) | 0.0218 (4) | −0.0027 (3) | 0.0068 (3) | 0.0023 (3) |
Cu4 | 0.0415 (5) | 0.0386 (5) | 0.0389 (5) | 0.0043 (4) | 0.0028 (4) | 0.0039 (4) |
O1 | 0.031 (2) | 0.040 (2) | 0.056 (3) | −0.0086 (19) | 0.018 (2) | −0.003 (2) |
N4 | 0.032 (3) | 0.040 (3) | 0.024 (3) | 0.001 (2) | 0.004 (3) | 0.001 (2) |
C5 | 0.044 (2) | 0.049 (2) | 0.0295 (18) | 0.0005 (15) | 0.0043 (15) | 0.0014 (15) |
N2 | 0.031 (3) | 0.039 (3) | 0.029 (3) | 0.002 (2) | 0.018 (3) | −0.007 (2) |
N1 | 0.025 (2) | 0.029 (2) | 0.026 (2) | −0.0008 (18) | 0.009 (2) | −0.004 (2) |
O2 | 0.032 (2) | 0.049 (3) | 0.044 (3) | −0.0079 (19) | 0.008 (2) | 0.003 (2) |
N3 | 0.028 (2) | 0.033 (2) | 0.023 (2) | −0.0015 (19) | 0.011 (2) | 0.0003 (19) |
C14 | 0.023 (3) | 0.023 (2) | 0.012 (2) | 0.002 (2) | 0.0084 (19) | 0.0002 (19) |
C15 | 0.033 (3) | 0.029 (3) | 0.030 (3) | −0.002 (2) | 0.015 (3) | 0.000 (2) |
C4 | 0.033 (2) | 0.052 (2) | 0.046 (2) | −0.0002 (17) | 0.0177 (18) | −0.0032 (18) |
C3 | 0.029 (4) | 0.047 (4) | 0.045 (5) | −0.003 (3) | 0.003 (3) | 0.003 (3) |
C13 | 0.036 (3) | 0.045 (3) | 0.042 (3) | −0.006 (3) | 0.034 (3) | −0.001 (3) |
C12 | 0.023 (3) | 0.047 (4) | 0.039 (4) | −0.002 (3) | 0.009 (3) | 0.002 (3) |
C1 | 0.028 (3) | 0.050 (4) | 0.029 (3) | −0.003 (3) | 0.015 (2) | −0.006 (3) |
C6 | 0.049 (4) | 0.032 (3) | 0.026 (3) | 0.000 (3) | 0.024 (3) | −0.002 (2) |
C17 | 0.044 (2) | 0.049 (2) | 0.0295 (18) | 0.0005 (15) | 0.0043 (15) | 0.0014 (15) |
C8 | 0.033 (2) | 0.052 (2) | 0.046 (2) | −0.0002 (17) | 0.0177 (18) | −0.0032 (18) |
C11 | 0.027 (3) | 0.045 (4) | 0.037 (3) | 0.004 (3) | 0.004 (2) | 0.000 (3) |
C9 | 0.031 (4) | 0.079 (6) | 0.096 (7) | 0.001 (4) | 0.037 (4) | −0.027 (5) |
C2 | 0.033 (2) | 0.052 (2) | 0.046 (2) | −0.0002 (17) | 0.0177 (18) | −0.0032 (18) |
C18 | 0.044 (2) | 0.049 (2) | 0.0295 (18) | 0.0005 (15) | 0.0043 (15) | 0.0014 (15) |
C7 | 0.044 (2) | 0.049 (2) | 0.0295 (18) | 0.0005 (15) | 0.0043 (15) | 0.0014 (15) |
C10 | 0.034 (3) | 0.041 (3) | 0.030 (3) | 0.002 (3) | 0.014 (3) | 0.005 (3) |
C16 | 0.061 (5) | 0.065 (5) | 0.023 (3) | −0.006 (4) | 0.015 (3) | 0.009 (3) |
Cu1A | 0.058 (11) | 0.046 (9) | 0.068 (12) | −0.003 (8) | 0.039 (10) | −0.004 (8) |
Br1A | 0.069 (10) | 0.064 (12) | 0.054 (9) | 0.000 (8) | 0.034 (8) | −0.002 (7) |
Cu3A | 0.0419 (5) | 0.0373 (5) | 0.0589 (6) | 0.0010 (4) | 0.0271 (5) | −0.0042 (4) |
Br2A | 0.071 (10) | 0.086 (14) | 0.036 (8) | 0.027 (9) | 0.037 (7) | 0.009 (8) |
Br6A | 0.058 (8) | 0.065 (11) | 0.051 (8) | −0.011 (9) | 0.025 (7) | −0.010 (8) |
Cu2A | 0.081 (12) | 0.049 (9) | 0.063 (10) | −0.005 (7) | 0.036 (9) | −0.006 (6) |
Br5A | 0.057 (9) | 0.104 (15) | 0.025 (7) | 0.025 (11) | 0.011 (6) | 0.026 (9) |
Cu4A | 0.0415 (5) | 0.0386 (5) | 0.0389 (5) | 0.0043 (4) | 0.0028 (4) | 0.0039 (4) |
Geometric parameters (Å, º) top
Br2—Cu1i | 2.6540 (11) | C14—C15 | 1.487 (9) |
Br2—Cu3 | 2.4046 (12) | C14—C13 | 1.390 (8) |
Br1—Cu1 | 2.3739 (10) | C15—C16 | 1.485 (9) |
Br1—Cu3 | 2.5098 (11) | C4—H4 | 0.9300 |
Br4—Cu3 | 2.6469 (12) | C4—C3 | 1.400 (10) |
Br4—Cu4 | 2.3990 (12) | C3—H3 | 0.9300 |
Br4—Cu3A | 2.634 (17) | C3—C2 | 1.374 (10) |
Br4—Cu4A | 2.357 (16) | C13—H13 | 0.9300 |
Br3—Cu3 | 2.3987 (11) | C13—C12 | 1.378 (9) |
Br3—Cu4ii | 2.6288 (12) | C12—H12 | 0.9300 |
Br3—Cu3A | 2.336 (16) | C12—C11 | 1.359 (10) |
Br3—Cu4Aii | 2.676 (18) | C1—H1A | 0.9300 |
Cu1—O1 | 2.008 (4) | C1—C2 | 1.381 (9) |
Cu1—N2 | 1.964 (5) | C6—C7 | 1.490 (9) |
Cu1—N1 | 1.992 (5) | C17—H17A | 0.9700 |
Br6—Cu2 | 2.3878 (11) | C17—H17B | 0.9700 |
Br6—Cu4iii | 2.5359 (14) | C17—C18 | 1.512 (11) |
Br5—Cu2 | 2.6357 (11) | C8—H8A | 0.9700 |
Br5—Cu4 | 2.4092 (14) | C8—H8B | 0.9700 |
Cu2—N4 | 1.968 (5) | C8—C9 | 1.455 (12) |
Cu2—O2 | 2.011 (4) | C11—H11 | 0.9300 |
Cu2—N3 | 1.993 (5) | C11—C10 | 1.387 (8) |
O1—H1 | 0.8200 | C9—H9 | 0.9300 |
O1—C9 | 1.448 (10) | C2—H2A | 0.9300 |
N4—C15 | 1.284 (8) | C18—H18A | 0.9700 |
N4—C17 | 1.462 (9) | C18—H18B | 0.9700 |
N4—Cu2A | 2.016 (15) | C7—H7A | 0.9600 |
C5—N1 | 1.372 (9) | C7—H7B | 0.9600 |
C5—C4 | 1.364 (10) | C7—H7C | 0.9600 |
C5—C6 | 1.479 (11) | C10—H10 | 0.9300 |
N2—C6 | 1.255 (8) | C16—H16A | 0.9600 |
N2—C8 | 1.473 (8) | C16—H16B | 0.9600 |
N2—Cu1A | 1.957 (18) | C16—H16C | 0.9600 |
N1—C1 | 1.338 (7) | Cu1A—Br1A | 2.67 (3) |
N1—Cu1A | 2.296 (18) | Cu1A—Br2Aiii | 2.34 (3) |
O2—H2 | 0.8200 | Br1A—Cu3A | 2.40 (2) |
O2—C18 | 1.443 (8) | Cu3A—Br2A | 2.62 (2) |
O2—Cu2A | 2.413 (16) | Br6A—Cu2A | 2.77 (2) |
N3—C14 | 1.348 (7) | Br6A—Cu4Aiii | 2.31 (2) |
N3—C10 | 1.351 (7) | Cu2A—Br5A | 2.23 (3) |
N3—Cu2A | 2.284 (17) | Br5A—Cu4A | 2.71 (3) |
Cu3—Br2—Cu1i | 129.92 (4) | C12—C13—C14 | 119.0 (5) |
Cu1—Br1—Cu3 | 115.93 (4) | C12—C13—H13 | 120.5 |
Cu4—Br4—Cu3 | 167.35 (5) | C13—C12—H12 | 120.3 |
Cu4A—Br4—Cu3A | 164.9 (6) | C11—C12—C13 | 119.5 (6) |
Cu3—Br3—Cu4ii | 159.31 (4) | C11—C12—H12 | 120.3 |
Cu3—Br3—Cu4Aii | 167.0 (3) | N1—C1—H1A | 118.8 |
Cu4ii—Br3—Cu4Aii | 17.7 (4) | N1—C1—C2 | 122.5 (6) |
Cu3A—Br3—Cu4Aii | 154.2 (5) | C2—C1—H1A | 118.8 |
Br1—Cu1—Br2iii | 99.38 (3) | C5—C6—C7 | 118.4 (6) |
O1—Cu1—Br2iii | 97.34 (14) | N2—C6—C5 | 115.2 (6) |
O1—Cu1—Br1 | 95.65 (14) | N2—C6—C7 | 126.4 (6) |
N2—Cu1—Br2iii | 104.87 (16) | N4—C17—H17A | 110.5 |
N2—Cu1—Br1 | 155.74 (16) | N4—C17—H17B | 110.5 |
N2—Cu1—O1 | 81.9 (2) | N4—C17—C18 | 106.3 (6) |
N2—Cu1—N1 | 80.5 (2) | H17A—C17—H17B | 108.7 |
N1—Cu1—Br2iii | 92.51 (13) | C18—C17—H17A | 110.5 |
N1—Cu1—Br1 | 98.12 (13) | C18—C17—H17B | 110.5 |
N1—Cu1—O1 | 161.5 (2) | N2—C8—H8A | 109.8 |
Cu2—Br6—Cu4iii | 116.82 (5) | N2—C8—H8B | 109.8 |
Cu4—Br5—Cu2 | 131.12 (6) | H8A—C8—H8B | 108.3 |
Br2—Cu3—Br1 | 104.21 (4) | C9—C8—N2 | 109.3 (6) |
Br2—Cu3—Br4 | 106.85 (4) | C9—C8—H8A | 109.8 |
Br1—Cu3—Br4 | 95.25 (4) | C9—C8—H8B | 109.8 |
Br3—Cu3—Br2 | 124.47 (5) | C12—C11—H11 | 120.0 |
Br3—Cu3—Br1 | 111.79 (4) | C12—C11—C10 | 119.9 (6) |
Br3—Cu3—Br4 | 110.23 (4) | C10—C11—H11 | 120.0 |
Br6—Cu2—Br5 | 99.05 (4) | O1—C9—C8 | 112.2 (6) |
N4—Cu2—Br6 | 152.70 (16) | O1—C9—H9 | 123.9 |
N4—Cu2—Br5 | 108.25 (16) | C8—C9—H9 | 123.9 |
N4—Cu2—O2 | 81.6 (2) | C3—C2—C1 | 118.8 (6) |
N4—Cu2—N3 | 80.6 (2) | C3—C2—H2A | 120.6 |
O2—Cu2—Br6 | 96.41 (13) | C1—C2—H2A | 120.6 |
O2—Cu2—Br5 | 95.09 (14) | O2—C18—C17 | 110.1 (6) |
N3—Cu2—Br6 | 97.65 (14) | O2—C18—H18A | 109.6 |
N3—Cu2—Br5 | 94.12 (14) | O2—C18—H18B | 109.6 |
N3—Cu2—O2 | 161.8 (2) | C17—C18—H18A | 109.6 |
Br4—Cu4—Br3iv | 112.04 (5) | C17—C18—H18B | 109.6 |
Br4—Cu4—Br6i | 107.88 (5) | H18A—C18—H18B | 108.1 |
Br4—Cu4—Br5 | 126.29 (6) | C6—C7—H7A | 109.5 |
Br6i—Cu4—Br3iv | 94.15 (4) | C6—C7—H7B | 109.5 |
Br5—Cu4—Br3iv | 107.49 (5) | C6—C7—H7C | 109.5 |
Br5—Cu4—Br6i | 103.88 (5) | H7A—C7—H7B | 109.5 |
Cu1—O1—H1 | 118.7 | H7A—C7—H7C | 109.5 |
C9—O1—Cu1 | 111.4 (4) | H7B—C7—H7C | 109.5 |
C9—O1—H1 | 109.5 | N3—C10—C11 | 121.1 (6) |
C15—N4—Cu2 | 117.6 (5) | N3—C10—H10 | 119.5 |
C15—N4—C17 | 125.6 (6) | C11—C10—H10 | 119.5 |
C15—N4—Cu2A | 111.8 (7) | C15—C16—H16A | 109.5 |
C17—N4—Cu2 | 116.5 (5) | C15—C16—H16B | 109.5 |
C17—N4—Cu2A | 114.4 (7) | C15—C16—H16C | 109.5 |
N1—C5—C6 | 113.1 (6) | H16A—C16—H16B | 109.5 |
C4—C5—N1 | 121.0 (7) | H16A—C16—H16C | 109.5 |
C4—C5—C6 | 125.9 (7) | H16B—C16—H16C | 109.5 |
C6—N2—Cu1 | 117.8 (4) | N2—Cu1A—N1 | 73.4 (6) |
C6—N2—C8 | 126.1 (5) | N2—Cu1A—Br1A | 102.5 (8) |
C6—N2—Cu1A | 109.5 (7) | N2—Cu1A—Br2Aiii | 158.1 (10) |
C8—N2—Cu1 | 115.6 (4) | N1—Cu1A—Br1A | 71.7 (6) |
C8—N2—Cu1A | 114.9 (7) | N1—Cu1A—Br2Aiii | 117.1 (8) |
C5—N1—Cu1 | 113.3 (4) | Br2Aiii—Cu1A—Br1A | 99.2 (8) |
C5—N1—Cu1A | 96.5 (6) | Cu3A—Br1A—Cu1A | 132.4 (8) |
C1—N1—Cu1 | 127.7 (4) | Br3—Cu3A—Br4 | 112.7 (6) |
C1—N1—C5 | 118.9 (5) | Br3—Cu3A—Br1A | 124.7 (8) |
C1—N1—Cu1A | 129.7 (6) | Br3—Cu3A—Br2A | 108.1 (7) |
Cu2—O2—H2 | 121.1 | Br1A—Cu3A—Br4 | 113.7 (8) |
C18—O2—Cu2 | 110.1 (4) | Br1A—Cu3A—Br2A | 101.9 (8) |
C18—O2—H2 | 109.5 | Br2A—Cu3A—Br4 | 88.0 (6) |
C18—O2—Cu2A | 89.2 (5) | Cu1Ai—Br2A—Cu3A | 116.4 (7) |
C14—N3—Cu2 | 113.5 (4) | Cu4Aiii—Br6A—Cu2A | 127.7 (9) |
C14—N3—C10 | 119.0 (5) | N4—Cu2A—O2 | 71.2 (5) |
C14—N3—Cu2A | 100.5 (5) | N4—Cu2A—N3 | 72.9 (5) |
C10—N3—Cu2 | 127.4 (4) | N4—Cu2A—Br6A | 104.3 (6) |
C10—N3—Cu2A | 127.8 (5) | N4—Cu2A—Br5A | 158.7 (9) |
N3—C14—C15 | 114.5 (5) | O2—Cu2A—Br6A | 67.2 (5) |
N3—C14—C13 | 121.4 (5) | N3—Cu2A—O2 | 114.6 (6) |
C13—C14—C15 | 124.0 (5) | N3—Cu2A—Br6A | 71.5 (5) |
N4—C15—C14 | 113.6 (6) | Br5A—Cu2A—O2 | 119.2 (9) |
N4—C15—C16 | 125.4 (6) | Br5A—Cu2A—N3 | 114.0 (8) |
C16—C15—C14 | 121.0 (6) | Br5A—Cu2A—Br6A | 97.0 (8) |
C5—C4—H4 | 120.2 | Cu2A—Br5A—Cu4A | 116.3 (8) |
C5—C4—C3 | 119.7 (7) | Br4—Cu4A—Br3iv | 111.8 (6) |
C3—C4—H4 | 120.2 | Br4—Cu4A—Br5A | 111.4 (8) |
C4—C3—H3 | 120.4 | Br3iv—Cu4A—Br5A | 89.4 (6) |
C2—C3—C4 | 119.1 (7) | Br6Ai—Cu4A—Br4 | 123.9 (9) |
C2—C3—H3 | 120.4 | Br6Ai—Cu4A—Br5A | 103.4 (8) |
C14—C13—H13 | 120.5 | ||
Cu1—O1—C9—C8 | −32.9 (9) | C4—C5—C6—N2 | 175.6 (7) |
Cu1—N2—C6—C5 | 4.5 (8) | C4—C5—C6—C7 | −4.4 (11) |
Cu1—N2—C6—C7 | −175.5 (5) | C4—C3—C2—C1 | −0.5 (11) |
Cu1—N2—C8—C9 | −17.9 (8) | C13—C14—C15—N4 | 177.2 (5) |
Cu1—N1—C1—C2 | 176.2 (5) | C13—C14—C15—C16 | −4.4 (9) |
Cu2—N4—C15—C14 | 3.6 (7) | C13—C12—C11—C10 | 1.6 (10) |
Cu2—N4—C15—C16 | −174.7 (5) | C12—C11—C10—N3 | 0.0 (10) |
Cu2—N4—C17—C18 | −22.2 (7) | C6—C5—N1—Cu1 | 3.6 (7) |
Cu2—O2—C18—C17 | −41.0 (6) | C6—C5—N1—C1 | −179.3 (5) |
Cu2—N3—C14—C15 | 4.2 (6) | C6—C5—N1—Cu1A | 38.0 (7) |
Cu2—N3—C14—C13 | −178.1 (4) | C6—C5—C4—C3 | 179.4 (7) |
Cu2—N3—C10—C11 | 176.0 (4) | C6—N2—C8—C9 | 170.8 (7) |
N4—C17—C18—O2 | 40.2 (7) | C17—N4—C15—C14 | 177.2 (6) |
C5—N1—C1—C2 | −0.4 (9) | C17—N4—C15—C16 | −1.0 (10) |
C5—C4—C3—C2 | 0.0 (11) | C8—N2—C6—C5 | 175.7 (6) |
N2—C8—C9—O1 | 32.5 (10) | C8—N2—C6—C7 | −4.3 (11) |
N1—C5—C4—C3 | 0.4 (11) | C10—N3—C14—C15 | −179.1 (5) |
N1—C5—C6—N2 | −5.4 (9) | C10—N3—C14—C13 | −1.4 (8) |
N1—C5—C6—C7 | 174.6 (6) | Cu1A—N2—C6—C5 | −40.2 (8) |
N1—C1—C2—C3 | 0.8 (10) | Cu1A—N2—C6—C7 | 139.8 (8) |
N3—C14—C15—N4 | −5.1 (7) | Cu1A—N2—C8—C9 | 28.3 (9) |
N3—C14—C15—C16 | 173.2 (6) | Cu1A—N1—C1—C2 | 128.3 (8) |
N3—C14—C13—C12 | 3.0 (9) | Cu2A—N4—C15—C14 | −36.4 (7) |
C14—N3—C10—C11 | −0.1 (9) | Cu2A—N4—C15—C16 | 145.4 (7) |
C14—C13—C12—C11 | −3.1 (10) | Cu2A—N4—C17—C18 | 18.5 (8) |
C15—N4—C17—C18 | 164.1 (6) | Cu2A—O2—C18—C17 | −64.7 (6) |
C15—C14—C13—C12 | −179.5 (6) | Cu2A—N3—C14—C15 | 36.2 (6) |
C4—C5—N1—Cu1 | −177.3 (5) | Cu2A—N3—C14—C13 | −146.1 (6) |
C4—C5—N1—C1 | −0.2 (10) | Cu2A—N3—C10—C11 | 133.8 (7) |
C4—C5—N1—Cu1A | −142.9 (7) |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iii) x, y+1, z; (iv) x, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Br3 | 0.82 | 2.43 | 3.240 (4) | 172 |
O2—H2···Br4iii | 0.82 | 2.40 | 3.206 (4) | 167 |
C4—H4···Br2v | 0.93 | 3.04 | 3.915 (8) | 158 |
C13—H13···Br5vi | 0.93 | 2.99 | 3.843 (6) | 154 |
C1—H1A···Br1 | 0.93 | 2.96 | 3.477 (6) | 117 |
C11—H11···Br3vi | 0.93 | 2.95 | 3.670 (6) | 136 |
C11—H11···Br5vii | 0.93 | 3.05 | 3.790 (7) | 138 |
C9—H9···Br5viii | 0.93 | 2.98 | 3.888 (8) | 166 |
C2—H2A···Br2ix | 0.93 | 3.09 | 3.818 (7) | 136 |
C2—H2A···Br4ix | 0.93 | 2.91 | 3.658 (7) | 139 |
C18—H18A···Br2iii | 0.97 | 3.02 | 3.965 (7) | 164 |
C18—H18B···Br4 | 0.97 | 3.13 | 4.086 (7) | 169 |
C7—H7C···Br1viii | 0.96 | 2.99 | 3.621 (7) | 125 |
C10—H10···Br6 | 0.93 | 2.98 | 3.482 (6) | 115 |
C16—H16A···Br6viii | 0.96 | 2.92 | 3.636 (7) | 133 |
Symmetry codes: (iii) x, y+1, z; (v) −x+2, −y+1, −z+2; (vi) −x+1, −y+1, −z+1; (vii) −x+1, y+1/2, −z+1/2; (viii) x, −y+3/2, z+1/2; (ix) −x+2, y+1/2, −z+3/2. |