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A new coordination polymer (CP), namely, poly[[diaquatris[μ2-1,4-bis(1H-imidazol-1-yl)benzene]bis[μ6-4-(2,4-dicarboxylatophenoxy)phthalato]tetracobalt(II)] hexahydrate], {[Co4(C16H6O9)2(C12H10N4)3(H2O)2]·6H2O}n, has been synthesized by solvothermal reaction. The CP was fully characterized by IR spectroscopy, elemental analysis, thermogravimetric analysis, and powder and single-crystal X-ray diffraction. It presents a three-dimensional (3D) structure based on tetranuclear CoII secondary building units (SBUs) with a tfz-d net and point symbol (43)2(46·618·84). The 4-(2,4-dicarboxyphenoxy)phthalic acid (H4dcppa) ligands are completely deprotonated and link {Co4(COO)4}4− SBUs into two-dimensional (2D) layers. Furthermore, adjacent layers are connected by 1,4-bis(1H-imidazol-1-yl)benzene (bib) ligands, giving rise to a 3D supramolecular architecture. Interestingly, there are numerous elliptical cavities in the CP where isolated unique discrete hexameric water clusters have been observed. The results of thermogravimetric and magnetic analyses are described in detail.
Supporting information
CCDC reference: 2020828
Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008) and
DIAMOND (Brandenburg, 2005); software used to prepare material for publication: pubCIF (Westrip, 2010).
Poly[[diaquatris[µ
2-1,4-bis(1
H-imidazol-1-yl)benzene]bis[µ
6-4-(2,4-dicarboxylatophenoxy)phthalato]tetracobalt(II)] hexahydrate]
top
Crystal data top
[Co4(C16H6O9)2(C12H10N4)3(H2O)2]·6H2O | Z = 1 |
Mr = 1694.98 | F(000) = 866 |
Triclinic, P1 | Dx = 1.705 Mg m−3 |
a = 10.660 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.240 (2) Å | Cell parameters from 9770 reflections |
c = 14.649 (3) Å | θ = 3.0–43.1° |
α = 109.48 (3)° | µ = 1.09 mm−1 |
β = 107.32 (3)° | T = 200 K |
γ = 98.87 (3)° | Block, purple |
V = 1650.6 (7) Å3 | 0.20 × 0.20 × 0.15 mm |
Data collection top
Bruker APEXII CCD diffractometer | 4994 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.032 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | θmax = 25.5°, θmin = 3.0° |
Tmin = 0.670, Tmax = 0.746 | h = −12→12 |
18817 measured reflections | k = −14→14 |
6077 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.050P)2 + 1.3022P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
6077 reflections | Δρmax = 0.43 e Å−3 |
496 parameters | Δρmin = −0.40 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 | |
Co1 | 0.30220 (3) | 0.91106 (3) | 0.44303 (2) | 0.01483 (10) | |
Co2 | 0.03427 (3) | 0.59524 (3) | 0.21886 (3) | 0.01792 (11) | |
C1 | −0.0100 (3) | 0.5924 (2) | 0.6859 (2) | 0.0207 (6) | |
C2 | −0.0542 (3) | 0.6032 (2) | 0.58218 (19) | 0.0172 (5) | |
C3 | 0.0289 (3) | 0.6830 (2) | 0.5610 (2) | 0.0180 (6) | |
H3 | 0.113147 | 0.735558 | 0.614728 | 0.022* | |
C4 | −0.1783 (3) | 0.5287 (3) | 0.5047 (2) | 0.0220 (6) | |
H4 | −0.235663 | 0.473281 | 0.517961 | 0.026* | |
C5 | −0.2191 (3) | 0.5347 (3) | 0.4078 (2) | 0.0218 (6) | |
H5 | −0.305520 | 0.485132 | 0.355426 | 0.026* | |
C6 | 0.0891 (2) | 0.7730 (2) | 0.44338 (19) | 0.0170 (5) | |
C7 | −0.0082 (3) | 0.6882 (2) | 0.46237 (19) | 0.0150 (5) | |
C8 | −0.1338 (2) | 0.6131 (2) | 0.38727 (19) | 0.0157 (5) | |
C9 | −0.3034 (2) | 0.6320 (2) | 0.25411 (19) | 0.0172 (5) | |
C10 | −0.4027 (3) | 0.5489 (3) | 0.1625 (2) | 0.0251 (6) | |
H10 | −0.383140 | 0.481731 | 0.119423 | 0.030* | |
C11 | −0.3300 (3) | 0.7325 (2) | 0.31297 (19) | 0.0187 (6) | |
H11 | −0.258127 | 0.792358 | 0.373777 | 0.022* | |
C12 | −0.5333 (3) | 0.5647 (3) | 0.1338 (2) | 0.0251 (6) | |
H12 | −0.602710 | 0.507628 | 0.070059 | 0.030* | |
C13 | −0.5647 (3) | 0.6613 (2) | 0.19548 (19) | 0.0182 (6) | |
C14 | −0.7146 (3) | 0.6614 (2) | 0.16267 (19) | 0.0202 (6) | |
C15 | −0.4601 (2) | 0.7481 (2) | 0.28507 (19) | 0.0165 (5) | |
C16 | −0.4850 (3) | 0.8560 (2) | 0.35692 (19) | 0.0185 (6) | |
C17 | 0.4719 (3) | 0.8334 (3) | 0.6131 (2) | 0.0265 (6) | |
H17 | 0.475133 | 0.903541 | 0.668145 | 0.032* | |
C18 | 0.4266 (3) | 0.6993 (3) | 0.4615 (2) | 0.0241 (6) | |
H18 | 0.389400 | 0.655655 | 0.387795 | 0.029* | |
C19 | 0.5073 (3) | 0.6643 (3) | 0.5305 (2) | 0.0273 (6) | |
H19 | 0.539183 | 0.594602 | 0.514564 | 0.033* | |
C20 | 0.6024 (3) | 0.7430 (3) | 0.7259 (2) | 0.0243 (6) | |
C21 | 0.5676 (4) | 0.7971 (4) | 0.8094 (3) | 0.0554 (12) | |
H21 | 0.499368 | 0.838685 | 0.802341 | 0.066* | |
C22 | 0.6976 (3) | 0.6793 (3) | 0.7356 (2) | 0.0341 (8) | |
H22 | 0.719498 | 0.639313 | 0.677109 | 0.041* | |
C23 | 0.7618 (3) | 0.6734 (3) | 0.8305 (2) | 0.0342 (8) | |
H23 | 0.827646 | 0.629361 | 0.836967 | 0.041* | |
C24 | 0.6320 (4) | 0.7911 (4) | 0.9040 (3) | 0.0529 (12) | |
H24 | 0.607907 | 0.828811 | 0.961830 | 0.063* | |
C25 | 0.7304 (3) | 0.7309 (3) | 0.9149 (2) | 0.0233 (6) | |
C26 | 0.8743 (3) | 0.6556 (3) | 1.0365 (2) | 0.0243 (6) | |
H26 | 0.885924 | 0.590813 | 0.984890 | 0.029* | |
C27 | 0.8075 (3) | 0.8106 (3) | 1.1090 (2) | 0.0255 (6) | |
H27 | 0.765512 | 0.874431 | 1.119897 | 0.031* | |
C28 | 0.8865 (3) | 0.7817 (3) | 1.1830 (2) | 0.0227 (6) | |
H28 | 0.909486 | 0.822821 | 1.255908 | 0.027* | |
C29 | 0.1245 (4) | 1.0731 (3) | 0.3724 (2) | 0.0369 (8) | |
H29 | 0.118484 | 1.109689 | 0.438638 | 0.044* | |
C30 | 0.1787 (3) | 0.9647 (3) | 0.2509 (2) | 0.0202 (6) | |
H30 | 0.217254 | 0.909329 | 0.213261 | 0.024* | |
C31 | 0.0625 (4) | 1.0938 (3) | 0.2873 (2) | 0.0373 (8) | |
H31 | 0.005451 | 1.145751 | 0.282588 | 0.045* | |
C32 | 0.0493 (3) | 1.0126 (2) | 0.1028 (2) | 0.0200 (6) | |
C33 | −0.0337 (4) | 1.0785 (4) | 0.0724 (2) | 0.0462 (10) | |
H33 | −0.057586 | 1.134163 | 0.122676 | 0.055* | |
C34 | 0.0837 (4) | 0.9341 (4) | 0.0304 (2) | 0.0455 (10) | |
H34 | 0.142101 | 0.887919 | 0.050205 | 0.055* | |
N1 | 0.1971 (2) | 0.9920 (2) | 0.34967 (16) | 0.0201 (5) | |
N2 | 0.0983 (2) | 1.0248 (2) | 0.20923 (16) | 0.0200 (5) | |
N3 | 0.9291 (2) | 0.6840 (2) | 1.13778 (17) | 0.0213 (5) | |
N4 | 0.7996 (2) | 0.7300 (2) | 1.01520 (17) | 0.0222 (5) | |
N5 | 0.5339 (2) | 0.7490 (2) | 0.62770 (17) | 0.0234 (5) | |
N6 | 0.4067 (2) | 0.8069 (2) | 0.51355 (17) | 0.0217 (5) | |
O1 | 0.10754 (18) | 0.74515 (17) | 0.35744 (13) | 0.0202 (4) | |
O2 | 0.1578 (2) | 0.87173 (18) | 0.51617 (15) | 0.0270 (5) | |
O3 | 0.0882 (2) | 0.6725 (2) | 0.76095 (15) | 0.0386 (6) | |
O4 | −0.0777 (2) | 0.50101 (18) | 0.68987 (14) | 0.0238 (4) | |
O5 | −0.17302 (18) | 0.61484 (18) | 0.28813 (13) | 0.0201 (4) | |
O6 | −0.38212 (19) | 0.92876 (17) | 0.43352 (15) | 0.0268 (5) | |
O7 | −0.60595 (18) | 0.86303 (17) | 0.33693 (13) | 0.0206 (4) | |
O8 | −0.78526 (19) | 0.60515 (19) | 0.19749 (16) | 0.0279 (5) | |
O9 | −0.7578 (2) | 0.7078 (2) | 0.09995 (15) | 0.0304 (5) | |
O10 | −0.0748 (2) | 0.4250 (2) | 0.10086 (16) | 0.0428 (6) | |
H10A | −0.129572 | 0.393769 | 0.039755 | 0.064* | |
H10B | −0.093545 | 0.381313 | 0.130602 | 0.064* | |
O11 | 0.6804 (4) | 0.0037 (3) | 0.2479 (3) | 0.0871 (11) | |
H11A | 0.692303 | 0.054983 | 0.219666 | 0.131* | |
H11B | 0.743095 | 0.036922 | 0.322513 | 0.131* | |
O12 | 0.6856 (4) | 0.1270 (4) | 0.1235 (3) | 0.1001 (13) | |
H12A | 0.644116 | 0.124202 | 0.065032 | 0.150* | |
H12B | 0.743591 | 0.193694 | 0.157552 | 0.150* | |
O13 | 0.4309 (4) | 0.8697 (4) | 0.0737 (4) | 0.1225 (17) | |
H13A | 0.378425 | 0.816711 | 0.079903 | 0.184* | |
H13B | 0.483745 | 0.914783 | 0.133583 | 0.184* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.01526 (18) | 0.01582 (19) | 0.01129 (17) | 0.00376 (14) | 0.00155 (13) | 0.00624 (14) |
Co2 | 0.01805 (19) | 0.0214 (2) | 0.01406 (18) | 0.00587 (15) | 0.00301 (14) | 0.00941 (16) |
C1 | 0.0289 (14) | 0.0214 (15) | 0.0209 (14) | 0.0143 (12) | 0.0144 (12) | 0.0115 (12) |
C2 | 0.0240 (13) | 0.0185 (13) | 0.0167 (12) | 0.0128 (11) | 0.0112 (11) | 0.0099 (11) |
C3 | 0.0192 (13) | 0.0191 (14) | 0.0162 (12) | 0.0070 (11) | 0.0059 (10) | 0.0077 (11) |
C4 | 0.0225 (14) | 0.0250 (15) | 0.0267 (14) | 0.0075 (12) | 0.0143 (12) | 0.0151 (13) |
C5 | 0.0161 (13) | 0.0281 (15) | 0.0213 (14) | 0.0042 (11) | 0.0055 (11) | 0.0123 (12) |
C6 | 0.0149 (12) | 0.0217 (14) | 0.0185 (13) | 0.0087 (11) | 0.0057 (10) | 0.0121 (12) |
C7 | 0.0188 (12) | 0.0158 (13) | 0.0150 (12) | 0.0083 (10) | 0.0093 (10) | 0.0076 (11) |
C8 | 0.0162 (12) | 0.0216 (14) | 0.0155 (12) | 0.0108 (11) | 0.0076 (10) | 0.0111 (11) |
C9 | 0.0115 (12) | 0.0275 (15) | 0.0164 (12) | 0.0060 (11) | 0.0048 (10) | 0.0136 (12) |
C10 | 0.0212 (14) | 0.0264 (15) | 0.0223 (14) | 0.0080 (12) | 0.0059 (12) | 0.0048 (13) |
C11 | 0.0150 (12) | 0.0227 (15) | 0.0117 (12) | 0.0010 (11) | −0.0001 (10) | 0.0055 (11) |
C12 | 0.0184 (13) | 0.0274 (16) | 0.0168 (13) | 0.0039 (12) | 0.0006 (11) | 0.0003 (12) |
C13 | 0.0160 (12) | 0.0242 (14) | 0.0144 (12) | 0.0056 (11) | 0.0045 (10) | 0.0090 (11) |
C14 | 0.0191 (13) | 0.0210 (14) | 0.0107 (12) | 0.0036 (11) | 0.0005 (10) | −0.0001 (11) |
C15 | 0.0152 (12) | 0.0182 (13) | 0.0152 (12) | 0.0042 (10) | 0.0037 (10) | 0.0079 (11) |
C16 | 0.0226 (14) | 0.0202 (14) | 0.0139 (12) | 0.0058 (11) | 0.0051 (11) | 0.0099 (11) |
C17 | 0.0324 (16) | 0.0293 (16) | 0.0210 (14) | 0.0167 (13) | 0.0079 (12) | 0.0123 (13) |
C18 | 0.0311 (15) | 0.0219 (15) | 0.0176 (13) | 0.0046 (12) | 0.0057 (12) | 0.0099 (12) |
C19 | 0.0383 (17) | 0.0197 (15) | 0.0226 (14) | 0.0106 (13) | 0.0079 (13) | 0.0090 (12) |
C20 | 0.0277 (15) | 0.0301 (16) | 0.0179 (13) | 0.0144 (13) | 0.0046 (12) | 0.0136 (12) |
C21 | 0.072 (3) | 0.089 (3) | 0.0318 (18) | 0.069 (3) | 0.0224 (18) | 0.034 (2) |
C22 | 0.0457 (19) | 0.046 (2) | 0.0185 (14) | 0.0296 (16) | 0.0118 (13) | 0.0153 (14) |
C23 | 0.0431 (18) | 0.045 (2) | 0.0242 (15) | 0.0324 (16) | 0.0117 (14) | 0.0177 (15) |
C24 | 0.069 (3) | 0.090 (3) | 0.0248 (17) | 0.062 (2) | 0.0250 (17) | 0.0283 (19) |
C25 | 0.0233 (14) | 0.0298 (16) | 0.0193 (14) | 0.0115 (12) | 0.0033 (11) | 0.0152 (13) |
C26 | 0.0273 (15) | 0.0293 (16) | 0.0192 (13) | 0.0140 (12) | 0.0066 (12) | 0.0124 (12) |
C27 | 0.0332 (16) | 0.0267 (16) | 0.0202 (14) | 0.0145 (13) | 0.0097 (12) | 0.0110 (13) |
C28 | 0.0260 (14) | 0.0257 (15) | 0.0173 (13) | 0.0074 (12) | 0.0083 (11) | 0.0096 (12) |
C29 | 0.055 (2) | 0.042 (2) | 0.0154 (14) | 0.0297 (17) | 0.0094 (14) | 0.0093 (14) |
C30 | 0.0214 (13) | 0.0249 (15) | 0.0174 (13) | 0.0119 (11) | 0.0050 (11) | 0.0117 (12) |
C31 | 0.056 (2) | 0.0404 (19) | 0.0227 (15) | 0.0377 (17) | 0.0131 (15) | 0.0125 (14) |
C32 | 0.0212 (13) | 0.0208 (14) | 0.0161 (12) | 0.0073 (11) | 0.0019 (10) | 0.0090 (11) |
C33 | 0.070 (2) | 0.063 (3) | 0.0202 (15) | 0.052 (2) | 0.0181 (16) | 0.0194 (17) |
C34 | 0.067 (2) | 0.065 (2) | 0.0241 (16) | 0.055 (2) | 0.0167 (16) | 0.0259 (17) |
N1 | 0.0229 (11) | 0.0214 (12) | 0.0148 (11) | 0.0079 (10) | 0.0038 (9) | 0.0078 (10) |
N2 | 0.0261 (12) | 0.0208 (12) | 0.0155 (11) | 0.0113 (10) | 0.0053 (9) | 0.0103 (10) |
N3 | 0.0213 (11) | 0.0267 (13) | 0.0176 (11) | 0.0080 (10) | 0.0050 (9) | 0.0125 (10) |
N4 | 0.0249 (12) | 0.0275 (13) | 0.0167 (11) | 0.0124 (10) | 0.0052 (9) | 0.0121 (10) |
N5 | 0.0281 (12) | 0.0265 (13) | 0.0184 (11) | 0.0142 (10) | 0.0048 (10) | 0.0130 (10) |
N6 | 0.0236 (12) | 0.0260 (13) | 0.0195 (11) | 0.0105 (10) | 0.0053 (9) | 0.0149 (10) |
O1 | 0.0231 (9) | 0.0215 (10) | 0.0165 (9) | 0.0045 (8) | 0.0074 (8) | 0.0091 (8) |
O2 | 0.0305 (11) | 0.0228 (11) | 0.0220 (10) | −0.0001 (9) | 0.0109 (9) | 0.0046 (9) |
O3 | 0.0521 (14) | 0.0335 (13) | 0.0184 (10) | −0.0036 (11) | 0.0030 (10) | 0.0122 (10) |
O4 | 0.0312 (10) | 0.0263 (11) | 0.0204 (10) | 0.0101 (9) | 0.0102 (8) | 0.0159 (9) |
O5 | 0.0165 (9) | 0.0336 (11) | 0.0163 (9) | 0.0115 (8) | 0.0071 (7) | 0.0145 (8) |
O6 | 0.0233 (10) | 0.0207 (10) | 0.0221 (10) | 0.0016 (8) | 0.0024 (8) | −0.0009 (9) |
O7 | 0.0207 (9) | 0.0281 (11) | 0.0151 (9) | 0.0136 (8) | 0.0057 (7) | 0.0091 (8) |
O8 | 0.0195 (10) | 0.0319 (12) | 0.0377 (12) | 0.0088 (9) | 0.0138 (9) | 0.0169 (10) |
O9 | 0.0234 (10) | 0.0449 (13) | 0.0205 (10) | 0.0104 (9) | 0.0009 (8) | 0.0164 (10) |
O10 | 0.0588 (15) | 0.0302 (13) | 0.0197 (11) | −0.0052 (11) | −0.0030 (10) | 0.0099 (10) |
O11 | 0.112 (3) | 0.078 (2) | 0.067 (2) | 0.032 (2) | 0.041 (2) | 0.0160 (19) |
O12 | 0.069 (2) | 0.109 (3) | 0.115 (3) | 0.000 (2) | 0.037 (2) | 0.044 (3) |
O13 | 0.086 (3) | 0.142 (4) | 0.144 (4) | −0.005 (3) | 0.021 (3) | 0.100 (3) |
Geometric parameters (Å, º) top
Co1—O6i | 2.011 (2) | C18—N6 | 1.369 (4) |
Co1—O7ii | 2.0479 (19) | C18—H18 | 0.9500 |
Co1—N1 | 2.107 (2) | C19—N5 | 1.366 (4) |
Co1—N6 | 2.137 (2) | C19—H19 | 0.9500 |
Co1—O2 | 2.202 (2) | C20—C21 | 1.370 (4) |
Co1—O1 | 2.336 (2) | C20—C22 | 1.374 (4) |
Co2—O8ii | 2.031 (2) | C20—N5 | 1.439 (3) |
Co2—O1 | 2.056 (2) | C21—C24 | 1.384 (4) |
Co2—O4iii | 2.059 (2) | C21—H21 | 0.9500 |
Co2—N3iv | 2.072 (2) | C22—C23 | 1.387 (4) |
Co2—O10 | 2.082 (2) | C22—H22 | 0.9500 |
C1—O3 | 1.243 (4) | C23—C25 | 1.370 (4) |
C1—O4 | 1.263 (3) | C23—H23 | 0.9500 |
C1—C2 | 1.508 (4) | C24—C25 | 1.372 (4) |
C2—C4 | 1.383 (4) | C24—H24 | 0.9500 |
C2—C3 | 1.391 (4) | C25—N4 | 1.439 (3) |
C3—C7 | 1.406 (4) | C26—N3 | 1.319 (3) |
C3—H3 | 0.9500 | C26—N4 | 1.351 (4) |
C4—C5 | 1.387 (4) | C26—H26 | 0.9500 |
C4—H4 | 0.9500 | C27—C28 | 1.346 (4) |
C5—C8 | 1.387 (4) | C27—N4 | 1.368 (4) |
C5—H5 | 0.9500 | C27—H27 | 0.9500 |
C6—O2 | 1.239 (3) | C28—N3 | 1.376 (4) |
C6—O1 | 1.274 (3) | C28—H28 | 0.9500 |
C6—C7 | 1.504 (4) | C29—C31 | 1.352 (4) |
C7—C8 | 1.385 (4) | C29—N1 | 1.366 (4) |
C8—O5 | 1.395 (3) | C29—H29 | 0.9500 |
C9—C10 | 1.366 (4) | C30—N1 | 1.317 (3) |
C9—C11 | 1.372 (4) | C30—N2 | 1.354 (3) |
C9—O5 | 1.404 (3) | C30—H30 | 0.9500 |
C10—C12 | 1.393 (4) | C31—N2 | 1.372 (4) |
C10—H10 | 0.9500 | C31—H31 | 0.9500 |
C11—C15 | 1.387 (3) | C32—C34 | 1.357 (4) |
C11—H11 | 0.9500 | C32—C33 | 1.363 (4) |
C12—C13 | 1.384 (4) | C32—N2 | 1.436 (3) |
C12—H12 | 0.9500 | C33—C34v | 1.384 (4) |
C13—C15 | 1.389 (4) | C33—H33 | 0.9500 |
C13—C14 | 1.526 (4) | C34—H34 | 0.9500 |
C14—O9 | 1.247 (3) | O10—H10A | 0.8245 |
C14—O8 | 1.267 (3) | O10—H10B | 0.8305 |
C15—C16 | 1.507 (4) | O11—H11A | 0.8725 |
C16—O6 | 1.247 (3) | O11—H11B | 0.9956 |
C16—O7 | 1.258 (3) | O12—H12A | 0.8251 |
C17—N6 | 1.313 (3) | O12—H12B | 0.8284 |
C17—N5 | 1.350 (4) | O13—H13A | 0.8362 |
C17—H17 | 0.9500 | O13—H13B | 0.8241 |
C18—C19 | 1.352 (4) | | |
| | | |
O6i—Co1—O7ii | 120.83 (9) | C18—C19—H19 | 126.7 |
O6i—Co1—N1 | 90.41 (9) | N5—C19—H19 | 126.7 |
O7ii—Co1—N1 | 85.73 (8) | C21—C20—C22 | 119.8 (3) |
O6i—Co1—N6 | 98.31 (9) | C21—C20—N5 | 119.3 (3) |
O7ii—Co1—N6 | 86.28 (8) | C22—C20—N5 | 120.8 (3) |
N1—Co1—N6 | 170.37 (8) | C20—C21—C24 | 119.8 (3) |
O6i—Co1—O2 | 85.36 (8) | C20—C21—H21 | 120.1 |
O7ii—Co1—O2 | 153.09 (8) | C24—C21—H21 | 120.1 |
N1—Co1—O2 | 101.30 (9) | C20—C22—C23 | 120.2 (3) |
N6—Co1—O2 | 83.58 (9) | C20—C22—H22 | 119.9 |
O6i—Co1—O1 | 140.87 (8) | C23—C22—H22 | 119.9 |
O7ii—Co1—O1 | 97.98 (8) | C25—C23—C22 | 120.0 (3) |
N1—Co1—O1 | 87.46 (8) | C25—C23—H23 | 120.0 |
N6—Co1—O1 | 88.34 (8) | C22—C23—H23 | 120.0 |
O2—Co1—O1 | 56.95 (7) | C25—C24—C21 | 120.5 (3) |
O8ii—Co2—O1 | 96.18 (9) | C25—C24—H24 | 119.7 |
O8ii—Co2—O4iii | 93.14 (8) | C21—C24—H24 | 119.7 |
O1—Co2—O4iii | 85.75 (8) | C23—C25—C24 | 119.6 (3) |
O8ii—Co2—N3iv | 106.81 (9) | C23—C25—N4 | 121.0 (2) |
O1—Co2—N3iv | 92.18 (9) | C24—C25—N4 | 119.4 (3) |
O4iii—Co2—N3iv | 160.04 (9) | N3—C26—N4 | 111.7 (2) |
O8ii—Co2—O10 | 97.82 (10) | N3—C26—H26 | 124.1 |
O1—Co2—O10 | 162.70 (9) | N4—C26—H26 | 124.1 |
O4iii—Co2—O10 | 83.39 (9) | C28—C27—N4 | 106.4 (2) |
N3iv—Co2—O10 | 93.45 (10) | C28—C27—H27 | 126.8 |
O3—C1—O4 | 124.5 (3) | N4—C27—H27 | 126.8 |
O3—C1—C2 | 119.0 (3) | C27—C28—N3 | 110.3 (2) |
O4—C1—C2 | 116.5 (2) | C27—C28—H28 | 124.8 |
C4—C2—C3 | 119.1 (2) | N3—C28—H28 | 124.8 |
C4—C2—C1 | 119.2 (2) | C31—C29—N1 | 110.4 (3) |
C3—C2—C1 | 121.7 (2) | C31—C29—H29 | 124.8 |
C2—C3—C7 | 121.9 (2) | N1—C29—H29 | 124.8 |
C2—C3—H3 | 119.1 | N1—C30—N2 | 111.9 (2) |
C7—C3—H3 | 119.1 | N1—C30—H30 | 124.0 |
C2—C4—C5 | 120.2 (3) | N2—C30—H30 | 124.0 |
C2—C4—H4 | 119.9 | C29—C31—N2 | 106.3 (3) |
C5—C4—H4 | 119.9 | C29—C31—H31 | 126.9 |
C4—C5—C8 | 120.1 (3) | N2—C31—H31 | 126.9 |
C4—C5—H5 | 120.0 | C34—C32—C33 | 118.8 (3) |
C8—C5—H5 | 120.0 | C34—C32—N2 | 120.6 (3) |
O2—C6—O1 | 119.1 (2) | C33—C32—N2 | 120.6 (2) |
O2—C6—C7 | 118.2 (2) | C32—C33—C34v | 121.2 (3) |
O1—C6—C7 | 122.6 (2) | C32—C33—H33 | 119.4 |
C8—C7—C3 | 117.3 (2) | C34v—C33—H33 | 119.4 |
C8—C7—C6 | 123.5 (2) | C32—C34—C33v | 120.0 (3) |
C3—C7—C6 | 119.2 (2) | C32—C34—H34 | 120.0 |
C7—C8—C5 | 121.5 (2) | C33v—C34—H34 | 120.0 |
C7—C8—O5 | 118.8 (2) | C30—N1—C29 | 105.1 (2) |
C5—C8—O5 | 119.7 (2) | C30—N1—Co1 | 125.32 (18) |
C10—C9—C11 | 120.5 (2) | C29—N1—Co1 | 129.30 (19) |
C10—C9—O5 | 119.8 (2) | C30—N2—C31 | 106.2 (2) |
C11—C9—O5 | 119.7 (2) | C30—N2—C32 | 127.6 (2) |
C9—C10—C12 | 118.5 (3) | C31—N2—C32 | 125.9 (2) |
C9—C10—H10 | 120.8 | C26—N3—C28 | 104.9 (2) |
C12—C10—H10 | 120.8 | C26—N3—Co2vi | 130.5 (2) |
C9—C11—C15 | 121.0 (2) | C28—N3—Co2vi | 124.12 (17) |
C9—C11—H11 | 119.5 | C26—N4—C27 | 106.7 (2) |
C15—C11—H11 | 119.5 | C26—N4—C25 | 127.8 (2) |
C13—C12—C10 | 121.9 (2) | C27—N4—C25 | 125.4 (2) |
C13—C12—H12 | 119.0 | C17—N5—C19 | 106.4 (2) |
C10—C12—H12 | 119.0 | C17—N5—C20 | 126.8 (2) |
C12—C13—C15 | 118.3 (2) | C19—N5—C20 | 126.6 (2) |
C12—C13—C14 | 117.2 (2) | C17—N6—C18 | 105.2 (2) |
C15—C13—C14 | 124.4 (2) | C17—N6—Co1 | 128.8 (2) |
O9—C14—O8 | 126.5 (3) | C18—N6—Co1 | 125.84 (18) |
O9—C14—C13 | 118.5 (2) | C6—O1—Co2 | 135.50 (18) |
O8—C14—C13 | 114.8 (2) | C6—O1—Co1 | 87.77 (15) |
C11—C15—C13 | 119.5 (2) | Co2—O1—Co1 | 134.61 (9) |
C11—C15—C16 | 118.4 (2) | C6—O2—Co1 | 94.86 (16) |
C13—C15—C16 | 122.0 (2) | C1—O4—Co2iii | 134.14 (18) |
O6—C16—O7 | 126.0 (2) | C8—O5—C9 | 113.13 (19) |
O6—C16—C15 | 115.8 (2) | C16—O6—Co1i | 147.55 (19) |
O7—C16—C15 | 118.1 (2) | C16—O7—Co1vii | 125.94 (16) |
N6—C17—N5 | 111.9 (3) | C14—O8—Co2vii | 138.55 (19) |
N6—C17—H17 | 124.0 | Co2—O10—H10A | 139.9 |
N5—C17—H17 | 124.0 | Co2—O10—H10B | 106.0 |
C19—C18—N6 | 109.9 (2) | H10A—O10—H10B | 107.9 |
C19—C18—H18 | 125.1 | H11A—O11—H11B | 111.4 |
N6—C18—H18 | 125.1 | H12A—O12—H12B | 107.7 |
C18—C19—N5 | 106.5 (3) | H13A—O13—H13B | 105.6 |
| | | |
O3—C1—C2—C4 | −167.3 (3) | C33—C32—C34—C33v | −0.6 (7) |
O4—C1—C2—C4 | 12.3 (4) | N2—C32—C34—C33v | 178.8 (3) |
O3—C1—C2—C3 | 15.1 (4) | N2—C30—N1—C29 | 0.3 (3) |
O4—C1—C2—C3 | −165.3 (2) | N2—C30—N1—Co1 | 175.15 (17) |
C4—C2—C3—C7 | −1.5 (4) | C31—C29—N1—C30 | 0.2 (4) |
C1—C2—C3—C7 | 176.1 (2) | C31—C29—N1—Co1 | −174.3 (2) |
C3—C2—C4—C5 | −0.5 (4) | N1—C30—N2—C31 | −0.7 (3) |
C1—C2—C4—C5 | −178.2 (2) | N1—C30—N2—C32 | −175.8 (3) |
C2—C4—C5—C8 | 1.8 (4) | C29—C31—N2—C30 | 0.8 (4) |
C2—C3—C7—C8 | 2.2 (4) | C29—C31—N2—C32 | 176.0 (3) |
C2—C3—C7—C6 | −177.5 (2) | C34—C32—N2—C30 | −0.6 (5) |
O2—C6—C7—C8 | 144.6 (3) | C33—C32—N2—C30 | 178.7 (3) |
O1—C6—C7—C8 | −38.5 (4) | C34—C32—N2—C31 | −174.8 (3) |
O2—C6—C7—C3 | −35.7 (3) | C33—C32—N2—C31 | 4.6 (5) |
O1—C6—C7—C3 | 141.1 (3) | N4—C26—N3—C28 | 0.1 (3) |
C3—C7—C8—C5 | −0.8 (4) | N4—C26—N3—Co2vi | 172.18 (19) |
C6—C7—C8—C5 | 178.8 (2) | C27—C28—N3—C26 | −0.1 (3) |
C3—C7—C8—O5 | −179.2 (2) | C27—C28—N3—Co2vi | −172.8 (2) |
C6—C7—C8—O5 | 0.5 (4) | N3—C26—N4—C27 | −0.1 (3) |
C4—C5—C8—C7 | −1.1 (4) | N3—C26—N4—C25 | 176.7 (3) |
C4—C5—C8—O5 | 177.2 (2) | C28—C27—N4—C26 | 0.0 (3) |
C11—C9—C10—C12 | −3.9 (4) | C28—C27—N4—C25 | −176.9 (3) |
O5—C9—C10—C12 | 176.4 (3) | C23—C25—N4—C26 | −16.8 (5) |
C10—C9—C11—C15 | 4.5 (4) | C24—C25—N4—C26 | 163.6 (3) |
O5—C9—C11—C15 | −175.7 (2) | C23—C25—N4—C27 | 159.5 (3) |
C9—C10—C12—C13 | −0.4 (5) | C24—C25—N4—C27 | −20.2 (5) |
C10—C12—C13—C15 | 4.0 (4) | N6—C17—N5—C19 | 0.9 (4) |
C10—C12—C13—C14 | −173.0 (3) | N6—C17—N5—C20 | −173.4 (3) |
C12—C13—C14—O9 | −88.1 (3) | C18—C19—N5—C17 | −1.9 (3) |
C15—C13—C14—O9 | 95.1 (3) | C18—C19—N5—C20 | 172.3 (3) |
C12—C13—C14—O8 | 86.9 (3) | C21—C20—N5—C17 | 24.2 (5) |
C15—C13—C14—O8 | −89.9 (3) | C22—C20—N5—C17 | −158.7 (3) |
C9—C11—C15—C13 | −0.8 (4) | C21—C20—N5—C19 | −149.0 (4) |
C9—C11—C15—C16 | 175.8 (2) | C22—C20—N5—C19 | 28.2 (5) |
C12—C13—C15—C11 | −3.4 (4) | N5—C17—N6—C18 | 0.6 (3) |
C14—C13—C15—C11 | 173.4 (3) | N5—C17—N6—Co1 | −175.52 (19) |
C12—C13—C15—C16 | −179.9 (3) | C19—C18—N6—C17 | −1.8 (3) |
C14—C13—C15—C16 | −3.1 (4) | C19—C18—N6—Co1 | 174.4 (2) |
C11—C15—C16—O6 | 5.0 (4) | O2—C6—O1—Co2 | 175.42 (18) |
C13—C15—C16—O6 | −178.5 (2) | C7—C6—O1—Co2 | −1.4 (4) |
C11—C15—C16—O7 | −172.7 (2) | O2—C6—O1—Co1 | 11.0 (2) |
C13—C15—C16—O7 | 3.8 (4) | C7—C6—O1—Co1 | −165.8 (2) |
N6—C18—C19—N5 | 2.4 (3) | O1—C6—O2—Co1 | −11.7 (3) |
C22—C20—C21—C24 | 2.3 (6) | C7—C6—O2—Co1 | 165.20 (19) |
N5—C20—C21—C24 | 179.5 (4) | O3—C1—O4—Co2iii | −26.4 (4) |
C21—C20—C22—C23 | −2.2 (6) | C2—C1—O4—Co2iii | 154.07 (18) |
N5—C20—C22—C23 | −179.4 (3) | C7—C8—O5—C9 | −128.1 (2) |
C20—C22—C23—C25 | 0.0 (5) | C5—C8—O5—C9 | 53.6 (3) |
C20—C21—C24—C25 | −0.2 (7) | C10—C9—O5—C8 | −122.9 (3) |
C22—C23—C25—C24 | 2.1 (5) | C11—C9—O5—C8 | 57.3 (3) |
C22—C23—C25—N4 | −177.5 (3) | O7—C16—O6—Co1i | −9.6 (6) |
C21—C24—C25—C23 | −2.0 (6) | C15—C16—O6—Co1i | 172.8 (2) |
C21—C24—C25—N4 | 177.6 (4) | O6—C16—O7—Co1vii | −41.7 (4) |
N4—C27—C28—N3 | 0.0 (3) | C15—C16—O7—Co1vii | 135.8 (2) |
N1—C29—C31—N2 | −0.7 (4) | O9—C14—O8—Co2vii | −23.3 (4) |
C34—C32—C33—C34v | 0.6 (7) | C13—C14—O8—Co2vii | 162.15 (19) |
N2—C32—C33—C34v | −178.8 (3) | | |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) x−1, y, z−1; (v) −x, −y+2, −z; (vi) x+1, y, z+1; (vii) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O11viii | 0.95 | 2.53 | 3.319 (4) | 140 |
C18—H18···O8ii | 0.95 | 2.65 | 3.523 (4) | 153 |
C21—H21···O12viii | 0.95 | 2.54 | 3.294 (5) | 136 |
C27—H27···O11ix | 0.95 | 2.51 | 3.314 (4) | 142 |
C30—H30···O9ii | 0.95 | 2.58 | 3.485 (4) | 160 |
C33—H33···O3i | 0.95 | 2.55 | 3.466 (4) | 163 |
O10—H10A···O9x | 0.82 | 1.89 | 2.696 (3) | 168 |
O10—H10B···O3iii | 0.83 | 1.90 | 2.697 (3) | 160 |
O11—H11A···O12 | 0.87 | 1.89 | 2.733 (6) | 164 |
O11—H11B···O2viii | 1.00 | 2.08 | 3.061 (4) | 167 |
O12—H12A···O13xi | 0.83 | 1.98 | 2.801 (6) | 172 |
O12—H12B···O3viii | 0.83 | 1.96 | 2.771 (4) | 166 |
O13—H13A···O9ii | 0.84 | 1.97 | 2.804 (4) | 173 |
O13—H13B···O11xii | 0.82 | 2.09 | 2.846 (6) | 152 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (viii) −x+1, −y+1, −z+1; (ix) x, y+1, z+1; (x) −x−1, −y+1, −z; (xi) −x+1, −y+1, −z; (xii) x, y+1, z. |
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