Naphthalene diimides, which are planar, chemically robust and redox-active, are an attractive class of electron-deficient dyes, which can undergo a single reversible one-electron reduction to form stable radical anions in the presence of electron donors upon irradiation. This makes them excellent candidates for organic linkers in the construction of photochromic coordination polymers. Such a photochromic one-dimensional linear coordination polymer has been prepared using N,N′-bis(3-carboxyphenyl)naphthalene-1,8:4,5-tetracarboximide (H2BBNDI). Crystallization of H2BBNDI with magnesium nitrate in an N,N′-dimethylformamide (DMF)/ethanol/H2O mixed-solvent system under solvothermal conditions afforded the one-dimensional coordination polymer catena-poly[[bis(dimethylformamide-κO)magnesium(II)]-bis[μ-N-(3-carboxylatophenyl)-N′-(3-carboxylphenyl)naphthalene-1,8:4,5-tetracarboximide-κ2O:O′]], [Mg(C28H13N2O8)2(C3H7NO)2]n. The asymmetric unit contains half of a magnesium cation, one HBBNDI− ligand and one DMF molecule. Two partially deprotonated HBBNDI− ligands bridge two magnesium cations to form a one-dimensional chain. Strong inter-chain π–π interactions between the naphthalene rings of the HBBNDI− ligand and the imide rings of adjacent chains provide a two-dimensional structure. The supramolecular three-dimensional framework is stabilized by π–π interactions between naphthalene rings of neighbouring two-dimensional supramolecular networks. The complex exhibits a reversible photochromic behaviour, which may originate from the photoinduced electron-transfer generation of radicals in the HBBNDI− ligand.
Supporting information
CCDC reference: 1547240
Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).
catena-Poly[[bis(dimethylformamide-
κO)magnesium(II)]bis[µ-
N-(3-carboxyphenyl)-
N'-(3-carboxylatophenyl)naphthalene-1,8:4,5-tetracarboximide-
κ2O:
O']]
top
Crystal data top
[Mg(C28H13N2O8)2(C3H7NO)2] | Z = 1 |
Mr = 1181.31 | F(000) = 610 |
Triclinic, P1 | Dx = 1.446 Mg m−3 |
a = 9.2595 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2711 (3) Å | Cell parameters from 4416 reflections |
c = 16.0049 (5) Å | θ = 2.6–30.3° |
α = 96.056 (3)° | µ = 0.12 mm−1 |
β = 92.679 (3)° | T = 153 K |
γ = 115.714 (4)° | Block, yellow |
V = 1356.47 (9) Å3 | 0.36 × 0.26 × 0.12 mm |
Data collection top
Rigaku Saturn 724 CCD area-detector diffractometer | 3779 reflections with I > 2σ(I) |
ω scans | Rint = 0.035 |
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998) | θmax = 26.4°, θmin = 2.7° |
Tmin = 0.755, Tmax = 1.000 | h = −10→11 |
11817 measured reflections | k = −12→12 |
5346 independent reflections | l = −15→19 |
Refinement top
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0702P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
5346 reflections | Δρmax = 0.28 e Å−3 |
399 parameters | Δρmin = −0.36 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 | |
Mg1 | 0.5000 | 0.5000 | 0.0000 | 0.0242 (2) | |
O1 | 0.66770 (18) | 0.67020 (17) | 0.08226 (9) | 0.0379 (4) | |
O2 | 0.8779 (2) | 0.83854 (18) | 0.02998 (10) | 0.0510 (5) | |
H2A | 0.861 (4) | 0.782 (3) | −0.0165 (11) | 0.076* | |
O3 | 0.86387 (16) | 0.79463 (18) | 0.43684 (9) | 0.0358 (4) | |
O4 | 0.53270 (16) | 0.97666 (16) | 0.33614 (9) | 0.0305 (3) | |
O5 | 0.32634 (17) | 0.48081 (17) | 0.73603 (9) | 0.0347 (4) | |
O6 | −0.04390 (16) | 0.58976 (15) | 0.60254 (9) | 0.0296 (3) | |
O7 | −0.32602 (17) | 0.47366 (16) | 0.93384 (9) | 0.0343 (4) | |
O8 | −0.1435 (2) | 0.68347 (17) | 0.89849 (10) | 0.0459 (4) | |
O9 | 0.49130 (18) | 0.64797 (17) | −0.07407 (9) | 0.0365 (4) | |
N1 | 0.69306 (18) | 0.87747 (17) | 0.38331 (9) | 0.0219 (4) | |
N2 | 0.14153 (18) | 0.53810 (17) | 0.67140 (10) | 0.0222 (4) | |
N3 | 0.4236 (2) | 0.8138 (2) | −0.12225 (14) | 0.0464 (5) | |
C1 | 0.7887 (3) | 0.7883 (2) | 0.08897 (13) | 0.0298 (5) | |
C2 | 0.8407 (2) | 0.8851 (2) | 0.17158 (12) | 0.0243 (4) | |
C3 | 0.9812 (2) | 1.0156 (2) | 0.18413 (13) | 0.0280 (5) | |
H3 | 1.0444 | 1.0470 | 0.1387 | 0.034* | |
C4 | 1.0286 (2) | 1.0994 (2) | 0.26247 (14) | 0.0317 (5) | |
H4 | 1.1252 | 1.1879 | 0.2710 | 0.038* | |
C5 | 0.9357 (2) | 1.0550 (2) | 0.32891 (13) | 0.0279 (5) | |
H5 | 0.9687 | 1.1121 | 0.3831 | 0.034* | |
C6 | 0.7942 (2) | 0.9263 (2) | 0.31519 (12) | 0.0225 (4) | |
C7 | 0.7459 (2) | 0.8410 (2) | 0.23772 (12) | 0.0234 (4) | |
H7 | 0.6489 | 0.7528 | 0.2293 | 0.028* | |
C8 | 0.5547 (2) | 0.9015 (2) | 0.38359 (12) | 0.0226 (4) | |
C9 | 0.7386 (2) | 0.8054 (2) | 0.44077 (12) | 0.0239 (4) | |
C10 | 0.6256 (2) | 0.7410 (2) | 0.50406 (12) | 0.0222 (4) | |
C11 | 0.4780 (2) | 0.7505 (2) | 0.50178 (11) | 0.0201 (4) | |
C12 | 0.4390 (2) | 0.8278 (2) | 0.44399 (11) | 0.0209 (4) | |
C13 | 0.2924 (2) | 0.8328 (2) | 0.44234 (12) | 0.0239 (4) | |
H13 | 0.2681 | 0.8873 | 0.4043 | 0.029* | |
C14 | 0.1790 (2) | 0.7579 (2) | 0.49646 (12) | 0.0228 (4) | |
H14 | 0.0767 | 0.7587 | 0.4932 | 0.027* | |
C15 | 0.2149 (2) | 0.6831 (2) | 0.55429 (12) | 0.0209 (4) | |
C16 | 0.3661 (2) | 0.6807 (2) | 0.55903 (11) | 0.0202 (4) | |
C17 | 0.4077 (2) | 0.6079 (2) | 0.61901 (11) | 0.0214 (4) | |
C18 | 0.5539 (2) | 0.6025 (2) | 0.62074 (12) | 0.0242 (4) | |
H18 | 0.5814 | 0.5543 | 0.6617 | 0.029* | |
C19 | 0.6625 (2) | 0.6677 (2) | 0.56230 (12) | 0.0242 (4) | |
H19 | 0.7619 | 0.6612 | 0.5630 | 0.029* | |
C20 | 0.2931 (2) | 0.5372 (2) | 0.68052 (12) | 0.0239 (4) | |
C21 | 0.0923 (2) | 0.6016 (2) | 0.60953 (12) | 0.0216 (4) | |
C22 | 0.0234 (2) | 0.4614 (2) | 0.72746 (12) | 0.0228 (4) | |
C23 | −0.0294 (2) | 0.3122 (2) | 0.72589 (12) | 0.0264 (5) | |
H23 | 0.0141 | 0.2613 | 0.6902 | 0.032* | |
C24 | −0.1461 (3) | 0.2386 (2) | 0.77713 (14) | 0.0323 (5) | |
H24 | −0.1834 | 0.1365 | 0.7764 | 0.039* | |
C25 | −0.2091 (3) | 0.3129 (2) | 0.82941 (13) | 0.0316 (5) | |
H25 | −0.2912 | 0.2612 | 0.8633 | 0.038* | |
C26 | −0.1523 (2) | 0.4632 (2) | 0.83249 (12) | 0.0267 (5) | |
C27 | −0.0345 (2) | 0.5377 (2) | 0.78099 (12) | 0.0264 (5) | |
H27 | 0.0055 | 0.6403 | 0.7828 | 0.032* | |
C28 | −0.2143 (3) | 0.5449 (2) | 0.89273 (13) | 0.0321 (5) | |
C29 | 0.3972 (3) | 0.7010 (2) | −0.08188 (14) | 0.0366 (5) | |
H29 | 0.2986 | 0.6585 | −0.0574 | 0.044* | |
C30 | 0.5740 (3) | 0.8808 (4) | −0.1608 (2) | 0.0744 (10) | |
H30A | 0.6498 | 0.9692 | −0.1239 | 0.112* | |
H30B | 0.5523 | 0.9065 | −0.2157 | 0.112* | |
H30C | 0.6209 | 0.8118 | −0.1687 | 0.112* | |
C31 | 0.3168 (4) | 0.8826 (3) | −0.1246 (2) | 0.0701 (9) | |
H31A | 0.2198 | 0.8260 | −0.0981 | 0.105* | |
H31B | 0.2865 | 0.8867 | −0.1834 | 0.105* | |
H31C | 0.3717 | 0.9819 | −0.0939 | 0.105* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mg1 | 0.0304 (5) | 0.0190 (5) | 0.0244 (5) | 0.0094 (4) | 0.0131 (4) | 0.0101 (4) |
O1 | 0.0405 (9) | 0.0329 (9) | 0.0280 (8) | 0.0036 (8) | 0.0107 (7) | 0.0070 (7) |
O2 | 0.0749 (12) | 0.0264 (9) | 0.0382 (9) | 0.0062 (9) | 0.0360 (9) | 0.0080 (7) |
O3 | 0.0240 (8) | 0.0555 (11) | 0.0389 (9) | 0.0233 (8) | 0.0142 (7) | 0.0221 (8) |
O4 | 0.0279 (8) | 0.0337 (9) | 0.0358 (8) | 0.0146 (7) | 0.0131 (6) | 0.0207 (7) |
O5 | 0.0269 (8) | 0.0432 (10) | 0.0368 (8) | 0.0133 (7) | 0.0085 (7) | 0.0245 (7) |
O6 | 0.0190 (7) | 0.0327 (9) | 0.0387 (8) | 0.0097 (7) | 0.0105 (6) | 0.0162 (7) |
O7 | 0.0396 (9) | 0.0284 (9) | 0.0393 (8) | 0.0146 (7) | 0.0254 (7) | 0.0159 (7) |
O8 | 0.0697 (11) | 0.0238 (9) | 0.0423 (9) | 0.0138 (8) | 0.0388 (8) | 0.0131 (7) |
O9 | 0.0418 (9) | 0.0344 (9) | 0.0412 (9) | 0.0195 (8) | 0.0142 (7) | 0.0221 (7) |
N1 | 0.0190 (8) | 0.0238 (9) | 0.0226 (8) | 0.0073 (7) | 0.0093 (7) | 0.0088 (7) |
N2 | 0.0184 (8) | 0.0223 (9) | 0.0257 (8) | 0.0066 (7) | 0.0086 (7) | 0.0102 (7) |
N3 | 0.0337 (11) | 0.0337 (12) | 0.0721 (15) | 0.0102 (9) | 0.0060 (10) | 0.0290 (11) |
C1 | 0.0372 (12) | 0.0218 (11) | 0.0315 (11) | 0.0113 (10) | 0.0147 (10) | 0.0120 (9) |
C2 | 0.0235 (10) | 0.0206 (10) | 0.0293 (10) | 0.0083 (9) | 0.0085 (8) | 0.0094 (8) |
C3 | 0.0248 (11) | 0.0263 (11) | 0.0346 (11) | 0.0092 (9) | 0.0158 (9) | 0.0150 (9) |
C4 | 0.0226 (11) | 0.0240 (12) | 0.0408 (12) | 0.0013 (9) | 0.0109 (9) | 0.0102 (10) |
C5 | 0.0253 (11) | 0.0244 (11) | 0.0304 (11) | 0.0070 (9) | 0.0083 (9) | 0.0044 (9) |
C6 | 0.0189 (10) | 0.0243 (11) | 0.0266 (10) | 0.0092 (9) | 0.0090 (8) | 0.0118 (8) |
C7 | 0.0192 (10) | 0.0197 (10) | 0.0302 (11) | 0.0058 (8) | 0.0067 (8) | 0.0106 (8) |
C8 | 0.0201 (10) | 0.0218 (11) | 0.0244 (10) | 0.0072 (9) | 0.0053 (8) | 0.0054 (8) |
C9 | 0.0217 (11) | 0.0255 (11) | 0.0244 (10) | 0.0094 (9) | 0.0056 (8) | 0.0061 (8) |
C10 | 0.0185 (10) | 0.0215 (10) | 0.0255 (10) | 0.0070 (8) | 0.0048 (8) | 0.0061 (8) |
C11 | 0.0183 (10) | 0.0176 (10) | 0.0221 (9) | 0.0052 (8) | 0.0050 (8) | 0.0035 (8) |
C12 | 0.0201 (10) | 0.0204 (10) | 0.0219 (9) | 0.0077 (8) | 0.0061 (8) | 0.0051 (8) |
C13 | 0.0231 (10) | 0.0248 (11) | 0.0245 (10) | 0.0100 (9) | 0.0038 (8) | 0.0088 (8) |
C14 | 0.0171 (10) | 0.0234 (11) | 0.0287 (10) | 0.0088 (9) | 0.0056 (8) | 0.0063 (8) |
C15 | 0.0181 (10) | 0.0192 (10) | 0.0238 (10) | 0.0058 (8) | 0.0061 (8) | 0.0049 (8) |
C16 | 0.0175 (10) | 0.0170 (10) | 0.0233 (10) | 0.0048 (8) | 0.0050 (8) | 0.0034 (8) |
C17 | 0.0201 (10) | 0.0188 (10) | 0.0222 (10) | 0.0055 (8) | 0.0036 (8) | 0.0041 (8) |
C18 | 0.0219 (10) | 0.0266 (11) | 0.0260 (10) | 0.0106 (9) | 0.0049 (8) | 0.0109 (8) |
C19 | 0.0168 (10) | 0.0270 (11) | 0.0291 (10) | 0.0091 (9) | 0.0041 (8) | 0.0067 (9) |
C20 | 0.0209 (10) | 0.0219 (11) | 0.0265 (10) | 0.0058 (9) | 0.0055 (8) | 0.0085 (8) |
C21 | 0.0183 (10) | 0.0199 (10) | 0.0258 (10) | 0.0072 (8) | 0.0040 (8) | 0.0053 (8) |
C22 | 0.0182 (10) | 0.0254 (11) | 0.0247 (10) | 0.0079 (9) | 0.0068 (8) | 0.0096 (8) |
C23 | 0.0249 (11) | 0.0248 (11) | 0.0307 (11) | 0.0109 (9) | 0.0094 (9) | 0.0060 (9) |
C24 | 0.0346 (12) | 0.0190 (11) | 0.0438 (13) | 0.0094 (10) | 0.0186 (10) | 0.0116 (9) |
C25 | 0.0302 (11) | 0.0269 (12) | 0.0375 (12) | 0.0085 (10) | 0.0189 (10) | 0.0145 (9) |
C26 | 0.0287 (11) | 0.0220 (11) | 0.0279 (10) | 0.0078 (9) | 0.0113 (9) | 0.0081 (8) |
C27 | 0.0261 (11) | 0.0203 (11) | 0.0300 (11) | 0.0061 (9) | 0.0086 (9) | 0.0085 (9) |
C28 | 0.0418 (13) | 0.0257 (12) | 0.0317 (11) | 0.0144 (10) | 0.0183 (10) | 0.0118 (9) |
C29 | 0.0319 (12) | 0.0322 (13) | 0.0435 (13) | 0.0094 (11) | 0.0072 (10) | 0.0163 (10) |
C30 | 0.0526 (17) | 0.067 (2) | 0.106 (2) | 0.0151 (16) | 0.0201 (17) | 0.064 (2) |
C31 | 0.0618 (19) | 0.0530 (19) | 0.106 (3) | 0.0335 (17) | −0.0045 (18) | 0.0232 (17) |
Geometric parameters (Å, º) top
Mg1—O1i | 2.0416 (15) | C8—C12 | 1.484 (3) |
Mg1—O1 | 2.0417 (15) | C9—C10 | 1.483 (3) |
Mg1—O9i | 2.0491 (14) | C10—C19 | 1.376 (3) |
Mg1—O9 | 2.0491 (14) | C10—C11 | 1.411 (3) |
Mg1—O7ii | 2.0656 (13) | C11—C12 | 1.411 (3) |
Mg1—O7iii | 2.0656 (13) | C11—C16 | 1.418 (3) |
O1—C1 | 1.233 (2) | C12—C13 | 1.379 (3) |
O2—C1 | 1.283 (2) | C13—C14 | 1.403 (3) |
O2—H2A | 0.855 (10) | C13—H13 | 0.9500 |
O3—C9 | 1.215 (2) | C14—C15 | 1.379 (3) |
O4—C8 | 1.208 (2) | C14—H14 | 0.9500 |
O5—C20 | 1.207 (2) | C15—C16 | 1.410 (3) |
O6—C21 | 1.212 (2) | C15—C21 | 1.482 (3) |
O7—C28 | 1.244 (2) | C16—C17 | 1.412 (3) |
O7—Mg1iv | 2.0657 (13) | C17—C18 | 1.379 (3) |
O8—C28 | 1.273 (3) | C17—C20 | 1.484 (3) |
O9—C29 | 1.219 (3) | C18—C19 | 1.404 (3) |
N1—C9 | 1.397 (2) | C18—H18 | 0.9500 |
N1—C8 | 1.406 (2) | C19—H19 | 0.9500 |
N1—C6 | 1.456 (2) | C22—C27 | 1.379 (3) |
N2—C21 | 1.402 (2) | C22—C23 | 1.389 (3) |
N2—C20 | 1.409 (2) | C23—C24 | 1.385 (3) |
N2—C22 | 1.454 (2) | C23—H23 | 0.9500 |
N3—C29 | 1.322 (3) | C24—C25 | 1.385 (3) |
N3—C31 | 1.445 (3) | C24—H24 | 0.9500 |
N3—C30 | 1.460 (3) | C25—C26 | 1.392 (3) |
C1—C2 | 1.488 (3) | C25—H25 | 0.9500 |
C2—C3 | 1.391 (3) | C26—C27 | 1.395 (3) |
C2—C7 | 1.392 (3) | C26—C28 | 1.504 (3) |
C3—C4 | 1.378 (3) | C27—H27 | 0.9500 |
C3—H3 | 0.9500 | C29—H29 | 0.9500 |
C4—C5 | 1.387 (3) | C30—H30A | 0.9800 |
C4—H4 | 0.9500 | C30—H30B | 0.9800 |
C5—C6 | 1.386 (3) | C30—H30C | 0.9800 |
C5—H5 | 0.9500 | C31—H31A | 0.9800 |
C6—C7 | 1.373 (3) | C31—H31B | 0.9800 |
C7—H7 | 0.9500 | C31—H31C | 0.9800 |
| | | |
O1i—Mg1—O1 | 180.0 | C12—C13—C14 | 120.41 (17) |
O1i—Mg1—O9i | 88.54 (6) | C12—C13—H13 | 119.8 |
O1—Mg1—O9i | 91.46 (6) | C14—C13—H13 | 119.8 |
O1i—Mg1—O9 | 91.46 (6) | C15—C14—C13 | 120.51 (16) |
O1—Mg1—O9 | 88.54 (6) | C15—C14—H14 | 119.7 |
O9i—Mg1—O9 | 180.0 | C13—C14—H14 | 119.7 |
O1i—Mg1—O7ii | 87.35 (6) | C14—C15—C16 | 120.01 (17) |
O1—Mg1—O7ii | 92.65 (6) | C14—C15—C21 | 119.79 (16) |
O9i—Mg1—O7ii | 88.16 (6) | C16—C15—C21 | 120.18 (16) |
O9—Mg1—O7ii | 91.84 (6) | C15—C16—C17 | 121.25 (17) |
O1i—Mg1—O7iii | 92.65 (6) | C15—C16—C11 | 119.58 (16) |
O1—Mg1—O7iii | 87.35 (6) | C17—C16—C11 | 119.17 (16) |
O9i—Mg1—O7iii | 91.84 (6) | C18—C17—C16 | 120.37 (17) |
O9—Mg1—O7iii | 88.16 (6) | C18—C17—C20 | 119.93 (16) |
O7ii—Mg1—O7iii | 180.0 | C16—C17—C20 | 119.70 (16) |
C1—O1—Mg1 | 145.30 (14) | C17—C18—C19 | 120.41 (17) |
C1—O2—H2A | 118 (2) | C17—C18—H18 | 119.8 |
C28—O7—Mg1iv | 139.00 (14) | C19—C18—H18 | 119.8 |
C29—O9—Mg1 | 132.21 (14) | C10—C19—C18 | 120.22 (16) |
C9—N1—C8 | 125.65 (15) | C10—C19—H19 | 119.9 |
C9—N1—C6 | 116.96 (14) | C18—C19—H19 | 119.9 |
C8—N1—C6 | 117.33 (14) | O5—C20—N2 | 120.80 (17) |
C21—N2—C20 | 125.00 (15) | O5—C20—C17 | 122.31 (17) |
C21—N2—C22 | 117.00 (14) | N2—C20—C17 | 116.89 (16) |
C20—N2—C22 | 117.93 (15) | O6—C21—N2 | 120.93 (17) |
C29—N3—C31 | 123.3 (2) | O6—C21—C15 | 122.49 (16) |
C29—N3—C30 | 119.0 (2) | N2—C21—C15 | 116.58 (15) |
C31—N3—C30 | 117.6 (2) | C27—C22—C23 | 121.17 (18) |
O1—C1—O2 | 125.8 (2) | C27—C22—N2 | 119.57 (17) |
O1—C1—C2 | 119.30 (18) | C23—C22—N2 | 119.26 (17) |
O2—C1—C2 | 114.94 (18) | C24—C23—C22 | 119.07 (18) |
C3—C2—C7 | 119.92 (18) | C24—C23—H23 | 120.5 |
C3—C2—C1 | 121.77 (18) | C22—C23—H23 | 120.5 |
C7—C2—C1 | 118.30 (17) | C23—C24—C25 | 120.44 (19) |
C4—C3—C2 | 120.03 (18) | C23—C24—H24 | 119.8 |
C4—C3—H3 | 120.0 | C25—C24—H24 | 119.8 |
C2—C3—H3 | 120.0 | C24—C25—C26 | 120.18 (19) |
C3—C4—C5 | 120.29 (19) | C24—C25—H25 | 119.9 |
C3—C4—H4 | 119.9 | C26—C25—H25 | 119.9 |
C5—C4—H4 | 119.9 | C25—C26—C27 | 119.51 (18) |
C6—C5—C4 | 119.15 (19) | C25—C26—C28 | 120.11 (18) |
C6—C5—H5 | 120.4 | C27—C26—C28 | 120.36 (18) |
C4—C5—H5 | 120.4 | C22—C27—C26 | 119.57 (19) |
C7—C6—C5 | 121.30 (18) | C22—C27—H27 | 120.2 |
C7—C6—N1 | 118.16 (17) | C26—C27—H27 | 120.2 |
C5—C6—N1 | 120.54 (17) | O7—C28—O8 | 125.51 (19) |
C6—C7—C2 | 119.28 (18) | O7—C28—C26 | 118.36 (19) |
C6—C7—H7 | 120.4 | O8—C28—C26 | 116.10 (18) |
C2—C7—H7 | 120.4 | O9—C29—N3 | 124.2 (2) |
O4—C8—N1 | 120.92 (16) | O9—C29—H29 | 117.9 |
O4—C8—C12 | 123.00 (16) | N3—C29—H29 | 117.9 |
N1—C8—C12 | 116.07 (16) | N3—C30—H30A | 109.5 |
O3—C9—N1 | 120.55 (17) | N3—C30—H30B | 109.5 |
O3—C9—C10 | 122.66 (17) | H30A—C30—H30B | 109.5 |
N1—C9—C10 | 116.77 (15) | N3—C30—H30C | 109.5 |
C19—C10—C11 | 120.61 (17) | H30A—C30—H30C | 109.5 |
C19—C10—C9 | 119.83 (16) | H30B—C30—H30C | 109.5 |
C11—C10—C9 | 119.51 (16) | N3—C31—H31A | 109.5 |
C12—C11—C10 | 121.68 (17) | N3—C31—H31B | 109.5 |
C12—C11—C16 | 119.15 (16) | H31A—C31—H31B | 109.5 |
C10—C11—C16 | 119.17 (16) | N3—C31—H31C | 109.5 |
C13—C12—C11 | 120.23 (17) | H31A—C31—H31C | 109.5 |
C13—C12—C8 | 119.90 (16) | H31B—C31—H31C | 109.5 |
C11—C12—C8 | 119.86 (16) | | |
| | | |
Mg1—O1—C1—O2 | −14.5 (4) | C12—C11—C16—C15 | 3.3 (3) |
Mg1—O1—C1—C2 | 165.48 (17) | C10—C11—C16—C15 | −176.68 (17) |
O1—C1—C2—C3 | 176.29 (18) | C12—C11—C16—C17 | −177.63 (17) |
O2—C1—C2—C3 | −3.8 (3) | C10—C11—C16—C17 | 2.4 (3) |
O1—C1—C2—C7 | −2.7 (3) | C15—C16—C17—C18 | 177.76 (17) |
O2—C1—C2—C7 | 177.24 (18) | C11—C16—C17—C18 | −1.3 (3) |
C7—C2—C3—C4 | 1.6 (3) | C15—C16—C17—C20 | −2.3 (3) |
C1—C2—C3—C4 | −177.42 (19) | C11—C16—C17—C20 | 178.64 (17) |
C2—C3—C4—C5 | −0.7 (3) | C16—C17—C18—C19 | −0.7 (3) |
C3—C4—C5—C6 | −0.6 (3) | C20—C17—C18—C19 | 179.34 (18) |
C4—C5—C6—C7 | 1.1 (3) | C11—C10—C19—C18 | −0.5 (3) |
C4—C5—C6—N1 | −179.29 (17) | C9—C10—C19—C18 | −178.01 (18) |
C9—N1—C6—C7 | 98.4 (2) | C17—C18—C19—C10 | 1.7 (3) |
C8—N1—C6—C7 | −79.0 (2) | C21—N2—C20—O5 | 179.47 (18) |
C9—N1—C6—C5 | −81.1 (2) | C22—N2—C20—O5 | −3.7 (3) |
C8—N1—C6—C5 | 101.4 (2) | C21—N2—C20—C17 | −0.6 (3) |
C5—C6—C7—C2 | −0.3 (3) | C22—N2—C20—C17 | 176.13 (16) |
N1—C6—C7—C2 | −179.90 (15) | C18—C17—C20—O5 | 4.2 (3) |
C3—C2—C7—C6 | −1.0 (3) | C16—C17—C20—O5 | −175.72 (18) |
C1—C2—C7—C6 | 177.99 (17) | C18—C17—C20—N2 | −175.69 (17) |
C9—N1—C8—O4 | 173.12 (18) | C16—C17—C20—N2 | 4.4 (3) |
C6—N1—C8—O4 | −9.7 (3) | C20—N2—C21—O6 | 175.29 (17) |
C9—N1—C8—C12 | −7.8 (3) | C22—N2—C21—O6 | −1.5 (3) |
C6—N1—C8—C12 | 169.41 (16) | C20—N2—C21—C15 | −4.9 (3) |
C8—N1—C9—O3 | −177.42 (18) | C22—N2—C21—C15 | 178.33 (16) |
C6—N1—C9—O3 | 5.4 (3) | C14—C15—C21—O6 | 4.9 (3) |
C8—N1—C9—C10 | 4.0 (3) | C16—C15—C21—O6 | −173.25 (18) |
C6—N1—C9—C10 | −173.18 (16) | C14—C15—C21—N2 | −174.98 (17) |
O3—C9—C10—C19 | 1.1 (3) | C16—C15—C21—N2 | 6.9 (3) |
N1—C9—C10—C19 | 179.66 (17) | C21—N2—C22—C27 | −63.7 (2) |
O3—C9—C10—C11 | −176.37 (18) | C20—N2—C22—C27 | 119.25 (19) |
N1—C9—C10—C11 | 2.2 (3) | C21—N2—C22—C23 | 116.12 (19) |
C19—C10—C11—C12 | 178.51 (18) | C20—N2—C22—C23 | −60.9 (2) |
C9—C10—C11—C12 | −4.0 (3) | C27—C22—C23—C24 | 2.2 (3) |
C19—C10—C11—C16 | −1.5 (3) | N2—C22—C23—C24 | −177.67 (17) |
C9—C10—C11—C16 | 176.00 (18) | C22—C23—C24—C25 | −0.2 (3) |
C10—C11—C12—C13 | 178.79 (17) | C23—C24—C25—C26 | −1.7 (3) |
C16—C11—C12—C13 | −1.2 (3) | C24—C25—C26—C27 | 1.6 (3) |
C10—C11—C12—C8 | 0.0 (3) | C24—C25—C26—C28 | −176.68 (19) |
C16—C11—C12—C8 | −179.96 (17) | C23—C22—C27—C26 | −2.2 (3) |
O4—C8—C12—C13 | 5.9 (3) | N2—C22—C27—C26 | 177.60 (16) |
N1—C8—C12—C13 | −173.19 (17) | C25—C26—C27—C22 | 0.3 (3) |
O4—C8—C12—C11 | −175.37 (18) | C28—C26—C27—C22 | 178.60 (18) |
N1—C8—C12—C11 | 5.6 (3) | Mg1iv—O7—C28—O8 | 21.2 (4) |
C11—C12—C13—C14 | −1.7 (3) | Mg1iv—O7—C28—C26 | −160.65 (15) |
C8—C12—C13—C14 | 177.03 (18) | C25—C26—C28—O7 | −6.0 (3) |
C12—C13—C14—C15 | 2.6 (3) | C27—C26—C28—O7 | 175.76 (19) |
C13—C14—C15—C16 | −0.4 (3) | C25—C26—C28—O8 | 172.3 (2) |
C13—C14—C15—C21 | −178.53 (18) | C27—C26—C28—O8 | −5.9 (3) |
C14—C15—C16—C17 | 178.45 (17) | Mg1—O9—C29—N3 | 168.06 (18) |
C21—C15—C16—C17 | −3.4 (3) | C31—N3—C29—O9 | −174.5 (2) |
C14—C15—C16—C11 | −2.5 (3) | C30—N3—C29—O9 | 0.3 (4) |
C21—C15—C16—C11 | 175.58 (17) | | |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z−1; (iii) −x, −y+1, −z+1; (iv) x−1, y, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O8ii | 0.86 (1) | 1.60 (1) | 2.447 (2) | 171 (3) |
Symmetry code: (ii) x+1, y, z−1. |