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The title coordination polymer, poly[bis[μ3-4-(3,2′:6′,3′′-terpyridin-4′-yl)benzoato]cadmium(II)], [Cd(C22H14N3O2)2]n or [Cd(3-cptpy)2]n, (I), has been synthesized solvothermally and characterized by IR spectroscopy, thermogravimetric analysis, and single-crystal and powder X-ray diffraction. The structure is composed of 3-cptpy− ligands bridging Cd atoms, with each Cd atom coordinated by six ligands and each ligand coordinating to three Cd atoms. Each Cd atom is in a slightly distorted trans-N2O4 octahedral environment, forming a two-dimensional layer structure with a (3,6)-connected topology. Layers are linked to each other by π–π stacking, resulting in a three-dimensional supramolecular framework. The strong luminescence and good thermal stability of (I) indicate that it can potentially be used as a luminescence sensor. The compound also shows a highly selective and sensitive response to 2,4,6-trinitrophenol through the luminescence quenching effect.
Supporting information
CCDC reference: 1906400
Data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: APEX2 (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXL2016 (Sheldrick, 2015); software used to prepare material for publication: publCIF (Westrip, 2010).
Poly[bis[µ
3-4-(3,2':6',3''-terpyridin-4'-yl)benzoato]cadmium(II)]
top
Crystal data top
[Cd(C22H14N3O2)2] | Z = 1 |
Mr = 817.12 | F(000) = 414 |
Triclinic, P1 | Dx = 1.639 Mg m−3 |
a = 5.0100 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5930 (4) Å | Cell parameters from 8991 reflections |
c = 17.3488 (8) Å | θ = 3.1–26.4° |
α = 91.192 (2)° | µ = 0.72 mm−1 |
β = 96.049 (2)° | T = 150 K |
γ = 92.858 (2)° | PILL, colorless |
V = 827.84 (6) Å3 | 0.20 × 0.15 × 0.10 mm |
Data collection top
Bruker D8 VENTURE diffractometer | 3329 reflections with I > 2σ(I) |
ω scans | Rint = 0.020 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | θmax = 26.4°, θmin = 3.1° |
Tmin = 0.660, Tmax = 0.745 | h = −6→6 |
5557 measured reflections | k = −11→11 |
3379 independent reflections | l = −21→21 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.060 | w = 1/[σ2(Fo2) + (0.0244P)2 + 0.2706P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
3379 reflections | Δρmax = 0.56 e Å−3 |
335 parameters | Δρmin = −0.81 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 | Occ. (<1) |
Cd1 | 0.500000 | 0.000000 | 1.000000 | 0.01297 (7) | |
C1 | 1.0308 (3) | 0.21232 (17) | 0.96914 (9) | 0.0136 (3) | |
O2 | 1.2054 (2) | 0.17352 (14) | 1.02003 (7) | 0.0209 (3) | |
N2 | 2.3320 (3) | 0.98504 (15) | 0.86811 (8) | 0.0153 (3) | |
C2 | 1.1168 (3) | 0.32288 (17) | 0.91458 (10) | 0.0132 (3) | |
N3 | 1.6941 (3) | 0.79443 (16) | 0.66123 (8) | 0.0163 (3) | |
C7 | 1.3176 (4) | 0.51630 (19) | 0.81297 (10) | 0.0174 (3) | |
C8 | 1.4414 (3) | 0.61444 (19) | 0.76015 (10) | 0.0173 (3) | |
C9 | 1.6566 (3) | 0.70589 (19) | 0.78812 (10) | 0.0170 (3) | |
H9 | 1.718309 | 0.709015 | 0.840630 | 0.020* | |
C10 | 1.7787 (3) | 0.79231 (18) | 0.73735 (10) | 0.0148 (3) | |
C11 | 1.4822 (3) | 0.70966 (19) | 0.63446 (10) | 0.0168 (3) | |
C12 | 1.3528 (3) | 0.61729 (19) | 0.68101 (10) | 0.0192 (4) | |
H12 | 1.209557 | 0.558388 | 0.659790 | 0.023* | |
C13 | 2.0141 (3) | 0.88879 (17) | 0.76415 (10) | 0.0129 (3) | |
C14 | 2.1191 (3) | 0.90117 (18) | 0.84179 (10) | 0.0154 (3) | |
H14 | 2.035985 | 0.847856 | 0.877505 | 0.018* | |
C15 | 2.1398 (4) | 0.9695 (2) | 0.71168 (10) | 0.0242 (4) | |
H15 | 2.064183 | 0.977275 | 0.660752 | 0.029* | |
C3A | 0.9619 (7) | 0.3645 (4) | 0.8521 (2) | 0.0158 (8) | 0.499 (3) |
H3A | 0.782249 | 0.333101 | 0.843929 | 0.019* | 0.499 (3) |
C4A | 1.0682 (8) | 0.4544 (4) | 0.7994 (2) | 0.0160 (8) | 0.499 (3) |
H4A | 0.963827 | 0.472302 | 0.753466 | 0.019* | 0.499 (3) |
C5A | 1.3856 (7) | 0.3762 (4) | 0.93061 (19) | 0.0153 (8) | 0.499 (3) |
H5A | 1.491225 | 0.349445 | 0.974614 | 0.018* | 0.499 (3) |
C6A | 1.4893 (7) | 0.4686 (4) | 0.8798 (2) | 0.0162 (8) | 0.499 (3) |
H6A | 1.668591 | 0.500606 | 0.888215 | 0.019* | 0.499 (3) |
C3B | 1.0847 (7) | 0.2982 (4) | 0.8326 (2) | 0.0142 (7) | 0.501 (3) |
H3B | 0.997962 | 0.215743 | 0.811842 | 0.017* | 0.501 (3) |
C4B | 1.1833 (8) | 0.3975 (4) | 0.78363 (19) | 0.0150 (7) | 0.501 (3) |
H4B | 1.156407 | 0.381948 | 0.730220 | 0.018* | 0.501 (3) |
C5B | 1.2208 (6) | 0.4520 (4) | 0.94186 (19) | 0.0139 (7) | 0.501 (3) |
H5B | 1.230328 | 0.472651 | 0.994723 | 0.017* | 0.501 (3) |
C6B | 1.3123 (6) | 0.5528 (3) | 0.89306 (19) | 0.0138 (7) | 0.501 (3) |
H6B | 1.368693 | 0.641934 | 0.912107 | 0.017* | 0.501 (3) |
N1A | 1.1884 (7) | 0.6239 (4) | 0.42824 (19) | 0.0272 (8) | 0.500 (3) |
C18A | 1.3875 (3) | 0.72172 (19) | 0.55086 (10) | 0.0176 (3) | 0.500 (3) |
C19A | 1.2790 (8) | 0.6140 (4) | 0.5036 (2) | 0.0232 (8) | 0.500 (3) |
H19A | 1.266320 | 0.526348 | 0.525207 | 0.028* | 0.500 (3) |
C20A | 1.4116 (7) | 0.8560 (4) | 0.5169 (2) | 0.0219 (8) | 0.500 (3) |
H20A | 1.488323 | 0.933101 | 0.546027 | 0.026* | 0.500 (3) |
C21A | 1.3171 (8) | 0.8679 (4) | 0.4393 (2) | 0.0250 (9) | 0.500 (3) |
H21A | 1.317850 | 0.954052 | 0.415694 | 0.030* | 0.500 (3) |
C22A | 1.2189 (5) | 0.7436 (3) | 0.39717 (11) | 0.0326 (5) | 0.500 (3) |
H22A | 1.174002 | 0.749258 | 0.343968 | 0.039* | 0.500 (3) |
N1B | 1.4920 (7) | 0.7617 (4) | 0.42099 (19) | 0.0300 (8) | 0.500 (3) |
C18B | 1.3875 (3) | 0.72172 (19) | 0.55086 (10) | 0.0176 (3) | 0.500 (3) |
C19B | 1.5638 (7) | 0.7522 (4) | 0.4972 (2) | 0.0217 (8) | 0.500 (3) |
H19B | 1.744861 | 0.767223 | 0.515047 | 0.026* | 0.500 (3) |
C20B | 1.1147 (8) | 0.6932 (5) | 0.5237 (2) | 0.0252 (9) | 0.500 (3) |
H20B | 0.989380 | 0.669399 | 0.557744 | 0.030* | 0.500 (3) |
C21B | 1.0381 (8) | 0.7015 (5) | 0.4448 (2) | 0.0317 (10) | 0.500 (3) |
H21B | 0.861629 | 0.677839 | 0.424875 | 0.038* | 0.500 (3) |
C22B | 1.2189 (5) | 0.7436 (3) | 0.39717 (11) | 0.0326 (5) | 0.500 (3) |
H22B | 1.158523 | 0.761499 | 0.345963 | 0.039* | 0.500 (3) |
C16A | 2.3879 (12) | 1.0403 (6) | 0.7390 (4) | 0.0169 (9) | 0.538 (6) |
H16A | 2.492199 | 1.082883 | 0.703969 | 0.020* | 0.538 (6) |
C17A | 2.4762 (14) | 1.0464 (7) | 0.8175 (5) | 0.0151 (10) | 0.538 (6) |
H17A | 2.638292 | 1.094169 | 0.834805 | 0.018* | 0.538 (6) |
C16B | 2.3185 (14) | 1.0787 (7) | 0.7379 (5) | 0.0169 (9) | 0.462 (6) |
H16B | 2.371949 | 1.147443 | 0.704885 | 0.020* | 0.462 (6) |
C17B | 2.4140 (16) | 1.0810 (9) | 0.8156 (6) | 0.0151 (10) | 0.462 (6) |
H17B | 2.541193 | 1.151142 | 0.833782 | 0.018* | 0.462 (6) |
O1A | 0.8147 (16) | 0.1497 (8) | 0.9547 (5) | 0.0170 (9) | 0.483 (9) |
O1B | 0.7699 (15) | 0.1864 (7) | 0.9647 (4) | 0.0170 (9) | 0.517 (9) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.01142 (9) | 0.01436 (10) | 0.01246 (10) | −0.00200 (6) | −0.00156 (6) | 0.00505 (6) |
C1 | 0.0174 (8) | 0.0099 (8) | 0.0126 (7) | −0.0019 (6) | −0.0004 (6) | −0.0001 (6) |
O2 | 0.0210 (6) | 0.0304 (7) | 0.0123 (6) | 0.0094 (5) | 0.0011 (5) | 0.0071 (5) |
N2 | 0.0163 (7) | 0.0148 (7) | 0.0143 (7) | −0.0039 (5) | 0.0013 (5) | −0.0019 (6) |
C2 | 0.0118 (7) | 0.0131 (8) | 0.0143 (8) | −0.0002 (6) | 0.0005 (6) | 0.0017 (6) |
N3 | 0.0159 (7) | 0.0192 (7) | 0.0127 (7) | −0.0037 (6) | −0.0017 (5) | 0.0044 (6) |
C7 | 0.0203 (8) | 0.0178 (9) | 0.0125 (8) | −0.0070 (7) | −0.0017 (6) | 0.0026 (7) |
C8 | 0.0184 (8) | 0.0189 (9) | 0.0133 (8) | −0.0057 (7) | −0.0019 (6) | 0.0024 (7) |
C9 | 0.0175 (8) | 0.0194 (9) | 0.0127 (8) | −0.0040 (7) | −0.0034 (6) | 0.0038 (7) |
C10 | 0.0135 (7) | 0.0163 (8) | 0.0134 (8) | −0.0012 (6) | −0.0036 (6) | 0.0023 (6) |
C11 | 0.0162 (8) | 0.0212 (9) | 0.0118 (8) | −0.0030 (6) | −0.0022 (6) | 0.0014 (7) |
C12 | 0.0176 (8) | 0.0243 (9) | 0.0136 (8) | −0.0088 (7) | −0.0034 (6) | 0.0021 (7) |
C13 | 0.0129 (7) | 0.0115 (8) | 0.0137 (8) | −0.0005 (6) | 0.0002 (6) | 0.0005 (6) |
C14 | 0.0142 (7) | 0.0161 (8) | 0.0148 (8) | −0.0036 (6) | −0.0016 (6) | 0.0037 (6) |
C15 | 0.0310 (10) | 0.0283 (10) | 0.0118 (8) | −0.0139 (8) | 0.0017 (7) | −0.0011 (7) |
C3A | 0.0121 (15) | 0.0139 (17) | 0.0205 (17) | −0.0034 (14) | −0.0014 (13) | 0.0019 (14) |
C4A | 0.0169 (17) | 0.0177 (18) | 0.0124 (16) | 0.0005 (15) | −0.0045 (14) | 0.0048 (14) |
C5A | 0.0171 (16) | 0.0151 (17) | 0.0128 (15) | −0.0002 (13) | −0.0018 (12) | 0.0020 (13) |
C6A | 0.0124 (15) | 0.0183 (17) | 0.0174 (16) | −0.0006 (12) | −0.0011 (12) | 0.0033 (14) |
C3B | 0.0142 (15) | 0.0108 (16) | 0.0160 (16) | −0.0047 (13) | −0.0030 (13) | 0.0001 (13) |
C4B | 0.0163 (16) | 0.0188 (18) | 0.0092 (15) | −0.0011 (15) | −0.0012 (13) | 0.0013 (14) |
C5B | 0.0141 (15) | 0.0161 (17) | 0.0109 (15) | −0.0019 (12) | −0.0009 (12) | 0.0023 (13) |
C6B | 0.0149 (15) | 0.0107 (15) | 0.0143 (16) | −0.0037 (12) | −0.0030 (12) | 0.0011 (13) |
N1A | 0.0313 (18) | 0.033 (2) | 0.0146 (15) | −0.0125 (15) | −0.0065 (13) | 0.0009 (14) |
C18A | 0.0181 (8) | 0.0221 (9) | 0.0116 (8) | −0.0024 (7) | −0.0022 (6) | 0.0030 (7) |
C19A | 0.0249 (18) | 0.025 (2) | 0.0172 (17) | −0.0096 (15) | −0.0035 (14) | 0.0055 (15) |
C20A | 0.0247 (18) | 0.0242 (19) | 0.0155 (17) | −0.0031 (14) | −0.0022 (14) | 0.0017 (14) |
C21A | 0.031 (2) | 0.026 (2) | 0.0162 (18) | −0.0017 (15) | −0.0042 (15) | 0.0078 (15) |
C22A | 0.0393 (11) | 0.0435 (13) | 0.0124 (9) | −0.0080 (10) | −0.0066 (8) | 0.0068 (9) |
N1B | 0.0369 (19) | 0.038 (2) | 0.0136 (15) | −0.0095 (15) | 0.0014 (14) | 0.0066 (14) |
C18B | 0.0181 (8) | 0.0221 (9) | 0.0116 (8) | −0.0024 (7) | −0.0022 (6) | 0.0030 (7) |
C19B | 0.0225 (17) | 0.024 (2) | 0.0169 (17) | −0.0061 (14) | −0.0014 (14) | 0.0049 (15) |
C20B | 0.0204 (18) | 0.040 (2) | 0.0145 (17) | −0.0027 (16) | −0.0013 (14) | 0.0012 (16) |
C21B | 0.0249 (19) | 0.048 (3) | 0.0193 (19) | −0.0013 (19) | −0.0092 (16) | 0.0009 (18) |
C22B | 0.0393 (11) | 0.0435 (13) | 0.0124 (9) | −0.0080 (10) | −0.0066 (8) | 0.0068 (9) |
C16A | 0.020 (3) | 0.015 (3) | 0.0161 (10) | −0.0036 (15) | 0.0043 (18) | 0.0019 (19) |
C17A | 0.011 (3) | 0.017 (3) | 0.0169 (10) | −0.0023 (17) | 0.001 (2) | −0.002 (2) |
C16B | 0.020 (3) | 0.015 (3) | 0.0161 (10) | −0.0036 (15) | 0.0043 (18) | 0.0019 (19) |
C17B | 0.011 (3) | 0.017 (3) | 0.0169 (10) | −0.0023 (17) | 0.001 (2) | −0.002 (2) |
O1A | 0.013 (2) | 0.017 (3) | 0.0204 (19) | −0.0044 (16) | −0.0011 (13) | 0.0058 (19) |
O1B | 0.013 (2) | 0.017 (3) | 0.0204 (19) | −0.0044 (16) | −0.0011 (13) | 0.0058 (19) |
Geometric parameters (Å, º) top
Cd1—O1A | 2.292 (9) | C15—H15 | 0.9300 |
Cd1—O1Ai | 2.292 (9) | C3A—C4A | 1.398 (5) |
Cd1—O1Bi | 2.320 (8) | C3A—H3A | 0.9300 |
Cd1—O1B | 2.320 (8) | C4A—H4A | 0.9300 |
Cd1—O2ii | 2.3236 (12) | C5A—C6A | 1.384 (5) |
Cd1—O2iii | 2.3236 (12) | C5A—H5A | 0.9300 |
Cd1—N2iv | 2.3522 (14) | C6A—H6A | 0.9300 |
Cd1—N2v | 2.3522 (14) | C3B—C4B | 1.396 (5) |
C1—O1A | 1.211 (9) | C3B—H3B | 0.9300 |
C1—O2 | 1.252 (2) | C4B—H4B | 0.9300 |
C1—O1B | 1.312 (8) | C5B—C6B | 1.390 (4) |
C1—C2 | 1.513 (2) | C5B—H5B | 0.9300 |
N2—C17A | 1.324 (8) | C6B—H6B | 0.9300 |
N2—C14 | 1.338 (2) | N1A—C22A | 1.288 (4) |
N2—C17B | 1.386 (10) | N1A—C19A | 1.345 (5) |
C2—C3A | 1.344 (4) | C18A—C19A | 1.360 (4) |
C2—C5B | 1.374 (4) | C18A—C20A | 1.433 (4) |
C2—C5A | 1.414 (4) | C19A—H19A | 0.9300 |
C2—C3B | 1.427 (4) | C20A—C21A | 1.388 (5) |
N3—C11 | 1.341 (2) | C20A—H20A | 0.9300 |
N3—C10 | 1.345 (2) | C21A—C22A | 1.424 (5) |
C7—C4A | 1.352 (4) | C21A—H21A | 0.9300 |
C7—C4B | 1.356 (4) | C22A—H22A | 0.9300 |
C7—C6B | 1.429 (4) | N1B—C19B | 1.340 (5) |
C7—C6A | 1.465 (4) | N1B—C22B | 1.388 (4) |
C7—C8 | 1.486 (2) | C18B—C19B | 1.375 (4) |
C8—C9 | 1.395 (2) | C18B—C20B | 1.410 (4) |
C8—C12 | 1.399 (2) | C19B—H19B | 0.9300 |
C9—C10 | 1.389 (2) | C20B—C21B | 1.387 (5) |
C9—H9 | 0.9300 | C20B—H20B | 0.9300 |
C10—C13 | 1.490 (2) | C21B—C22B | 1.342 (5) |
C11—C12 | 1.393 (2) | C21B—H21B | 0.9300 |
C11—C18B | 1.486 (2) | C22B—H22B | 0.9300 |
C11—C18A | 1.486 (2) | C16A—C17A | 1.387 (10) |
C12—H12 | 0.9300 | C16A—H16A | 0.9300 |
C13—C15 | 1.388 (2) | C17A—H17A | 0.9300 |
C13—C14 | 1.394 (2) | C16B—C17B | 1.381 (13) |
C14—H14 | 0.9300 | C16B—H16B | 0.9300 |
C15—C16B | 1.381 (8) | C17B—H17B | 0.9300 |
C15—C16A | 1.417 (7) | | |
| | | |
O1A—Cd1—O1Ai | 180.0 | C2—C3A—H3A | 119.7 |
O1A—Cd1—O1Bi | 168.40 (16) | C4A—C3A—H3A | 119.7 |
O1Ai—Cd1—O1Bi | 11.60 (16) | C7—C4A—C3A | 122.2 (3) |
O1Bi—Cd1—O1B | 180.0 (4) | C7—C4A—H4A | 118.9 |
O1A—Cd1—O2ii | 94.29 (16) | C3A—C4A—H4A | 118.9 |
O1Ai—Cd1—O2ii | 85.71 (17) | C6A—C5A—C2 | 119.0 (3) |
O1A—Cd1—O2iii | 85.71 (16) | C6A—C5A—H5A | 120.5 |
O1Ai—Cd1—O2iii | 94.29 (17) | C2—C5A—H5A | 120.5 |
O2ii—Cd1—O2iii | 180.0 | C5A—C6A—C7 | 120.2 (3) |
O1A—Cd1—N2iv | 82.4 (2) | C5A—C6A—H6A | 119.9 |
O1Ai—Cd1—N2iv | 97.6 (2) | C7—C6A—H6A | 119.9 |
O2ii—Cd1—N2iv | 89.77 (5) | C4B—C3B—C2 | 120.1 (3) |
O2iii—Cd1—N2iv | 90.23 (5) | C4B—C3B—H3B | 119.9 |
O1A—Cd1—N2v | 97.6 (2) | C2—C3B—H3B | 119.9 |
O1Ai—Cd1—N2v | 82.4 (2) | C7—C4B—C3B | 120.8 (3) |
O2ii—Cd1—N2v | 90.23 (5) | C7—C4B—H4B | 119.6 |
O2iii—Cd1—N2v | 89.77 (5) | C3B—C4B—H4B | 119.6 |
N2iv—Cd1—N2v | 180.0 | C2—C5B—C6B | 122.2 (3) |
O1A—C1—O2 | 122.1 (4) | C2—C5B—H5B | 118.9 |
O2—C1—O1B | 127.5 (4) | C6B—C5B—H5B | 118.9 |
O1A—C1—C2 | 119.3 (4) | C5B—C6B—C7 | 118.5 (3) |
O2—C1—C2 | 117.40 (15) | C5B—C6B—H6B | 120.7 |
O1B—C1—C2 | 114.0 (3) | C7—C6B—H6B | 120.7 |
C1—O2—Cd1vi | 124.00 (11) | C22A—N1A—C19A | 117.4 (3) |
C17A—N2—C14 | 118.9 (4) | C19A—C18A—C20A | 117.1 (3) |
C14—N2—C17B | 115.1 (4) | C19A—C18A—C11 | 124.8 (2) |
C17A—N2—Cd1vii | 118.1 (4) | C20A—C18A—C11 | 118.2 (2) |
C14—N2—Cd1vii | 122.24 (11) | N1A—C19A—C18A | 125.4 (3) |
C3A—C2—C5A | 120.5 (2) | N1A—C19A—H19A | 117.3 |
C5B—C2—C3B | 117.6 (2) | C18A—C19A—H19A | 117.3 |
C3A—C2—C1 | 124.4 (2) | C21A—C20A—C18A | 118.1 (3) |
C5B—C2—C1 | 121.30 (19) | C21A—C20A—H20A | 120.9 |
C5A—C2—C1 | 114.96 (19) | C18A—C20A—H20A | 120.9 |
C3B—C2—C1 | 121.05 (19) | C20A—C21A—C22A | 117.7 (3) |
C11—N3—C10 | 117.76 (14) | C20A—C21A—H21A | 121.2 |
C4B—C7—C6B | 119.2 (2) | C22A—C21A—H21A | 121.2 |
C4A—C7—C6A | 116.8 (2) | N1A—C22A—C21A | 124.0 (3) |
C4A—C7—C8 | 125.0 (2) | N1A—C22A—H22A | 118.0 |
C4B—C7—C8 | 119.8 (2) | C21A—C22A—H22A | 118.0 |
C6B—C7—C8 | 120.70 (19) | C19B—N1B—C22B | 116.0 (3) |
C6A—C7—C8 | 117.67 (19) | C19B—C18B—C20B | 118.0 (2) |
C9—C8—C12 | 117.45 (15) | C19B—C18B—C11 | 121.4 (2) |
C9—C8—C7 | 120.49 (15) | C20B—C18B—C11 | 120.5 (2) |
C12—C8—C7 | 122.04 (16) | N1B—C19B—C18B | 124.3 (3) |
C10—C9—C8 | 119.85 (16) | N1B—C19B—H19B | 117.8 |
C10—C9—H9 | 120.1 | C18B—C19B—H19B | 117.8 |
C8—C9—H9 | 120.1 | C21B—C20B—C18B | 118.2 (3) |
N3—C10—C9 | 122.61 (16) | C21B—C20B—H20B | 120.9 |
N3—C10—C13 | 115.61 (15) | C18B—C20B—H20B | 120.9 |
C9—C10—C13 | 121.77 (15) | C22B—C21B—C20B | 120.0 (3) |
N3—C11—C12 | 123.25 (16) | C22B—C21B—H21B | 120.0 |
N3—C11—C18B | 115.60 (15) | C20B—C21B—H21B | 120.0 |
C12—C11—C18B | 121.14 (16) | C21B—C22B—N1B | 122.9 (3) |
N3—C11—C18A | 115.60 (15) | C21B—C22B—H22B | 118.6 |
C12—C11—C18A | 121.14 (16) | N1B—C22B—H22B | 118.6 |
C11—C12—C8 | 119.03 (16) | C17A—C16A—C15 | 120.5 (5) |
C11—C12—H12 | 120.5 | C17A—C16A—H16A | 119.8 |
C8—C12—H12 | 120.5 | C15—C16A—H16A | 119.8 |
C15—C13—C14 | 117.22 (16) | N2—C17A—C16A | 120.6 (6) |
C15—C13—C10 | 120.64 (15) | N2—C17A—H17A | 119.7 |
C14—C13—C10 | 122.14 (15) | C16A—C17A—H17A | 119.7 |
N2—C14—C13 | 124.04 (15) | C15—C16B—C17B | 116.8 (7) |
N2—C14—H14 | 118.0 | C15—C16B—H16B | 121.6 |
C13—C14—H14 | 118.0 | C17B—C16B—H16B | 121.6 |
C16B—C15—C13 | 120.1 (4) | C16B—C17B—N2 | 124.1 (8) |
C13—C15—C16A | 117.3 (3) | C16B—C17B—H17B | 118.0 |
C16B—C15—H15 | 114.2 | N2—C17B—H17B | 118.0 |
C13—C15—H15 | 121.4 | C1—O1A—Cd1 | 145.8 (6) |
C16A—C15—H15 | 121.3 | C1—O1B—Cd1 | 133.7 (4) |
C2—C3A—C4A | 120.6 (3) | | |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x−1, y, z; (iii) −x+2, −y, −z+2; (iv) x−2, y−1, z; (v) −x+3, −y+1, −z+2; (vi) x+1, y, z; (vii) x+2, y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C21B—H21B···N1Bii | 0.93 | 2.05 | 2.814 (6) | 138 |
C14—H14···O2v | 0.93 | 2.26 | 3.111 (2) | 152 |
Symmetry codes: (ii) x−1, y, z; (v) −x+3, −y+1, −z+2. |
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