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In recent years, the design and construction of crystalline coordination complexes by the assembly of metal ions with multitopic ligands have attracted considerable attention because of the unique architectures and potential applications of these compounds. Two new coordination polymers, namely poly[[μ-trans-1-(2-aminopyridin-3-yl)-2-(pyridin-4-yl)ethene-κ2N:N′](μ3-5-methylisophthalato-κ4O1,O1′:O3:O3′)cadmium(II)], [Cd(C9H6O4)(C12H11N3)]n or [Cd(5-Me-ip)(2-NH2-3,4-bpe)]n, (I), and poly[[μ-trans-1-(2-aminopyridin-3-yl)-2-(pyridin-4-yl)ethene-κ2N:N′](μ2-5-hydroxyisophthalato-κ4O1,O1′:O3:O5)cadmium(II)], [Cd(C8H4O5)(C12H11N3)]n or [Cd(5-HO-ip)(2-NH2-3,4-bpe)]n, (II), have been prepared hydrothermally by the self-assembly of Cd(NO3)2·4H2O and trans-1-(2-aminopyridin-3-yl)-2-(pyridin-4-yl)ethene (2-NH2-3,4-bpe) with two similar dicarboxylic acids, i.e. 5-methylisophthalic acid (5-Me-H2ip) and 5-hydroxyisophthalic acid (5-HO-H2ip). The coordination network of (I) is a two-dimensional sql net parallel to (101). Adjacent sql nets are further linked to form a three-dimensional supramolecular framework via hydrogen-bonding interactions. Compound (II) is a two-dimensional (3,5)-connected coordination network parallel to (010) with the point symbol (63)(55647). As the other reactants and reaction conditions are the same, the structural differences between (I) and (II) are undoubtedly determined by the different substituent groups in the 5-position of isophthalic acid. Both (I) and (II) exhibit good thermal stabilities and photoluminescence properties.
Supporting information
CCDC references: 1847867; 1847866
For both structures, data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).
Poly[[µ-
trans-1-(2-aminopyridin-3-yl)-2-(pyridin-4-yl)ethene-
κ2N:
N'](µ
3-5-methylisophthalato-
κ4O1,
O1':
O3:
O3')cadmium(II)] (I)
top
Crystal data top
[Cd(C9H6O4)(C12H11N3)] | Z = 2 |
Mr = 487.79 | F(000) = 488 |
Triclinic, P1 | Dx = 1.670 Mg m−3 |
a = 9.1432 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.439 (2) Å | Cell parameters from 18239 reflections |
c = 10.872 (2) Å | θ = 2.9–27.5° |
α = 73.04 (3)° | µ = 1.16 mm−1 |
β = 83.23 (3)° | T = 223 K |
γ = 78.38 (3)° | Block, yellow |
V = 970.3 (4) Å3 | 0.15 × 0.12 × 0.09 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 4098 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
phi and ω scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −11→11 |
Tmin = 0.853, Tmax = 0.921 | k = −13→12 |
18239 measured reflections | l = −14→14 |
4439 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H-atom parameters constrained |
wR(F2) = 0.047 | w = 1/[σ2(Fo2) + (0.0223P)2 + 0.2967P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
4439 reflections | Δρmax = 0.30 e Å−3 |
263 parameters | Δρmin = −0.38 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 | |
Cd1 | 0.56849 (2) | 0.61041 (2) | 0.12454 (2) | 0.02469 (5) | |
N1 | 0.32820 (17) | 0.65631 (15) | 0.23650 (14) | 0.0302 (3) | |
N2 | −0.21538 (17) | 0.60912 (16) | 0.98484 (14) | 0.0335 (3) | |
N3 | 0.36552 (19) | 0.48024 (17) | 0.42089 (15) | 0.0395 (4) | |
H3A | 0.4432 | 0.4432 | 0.3809 | 0.047* | |
H3B | 0.3406 | 0.4401 | 0.5005 | 0.047* | |
O1 | 0.59215 (16) | 0.39300 (12) | 0.22758 (12) | 0.0360 (3) | |
O2 | 0.56716 (16) | 0.32934 (13) | 0.05469 (12) | 0.0373 (3) | |
O3 | 0.57903 (16) | −0.16824 (12) | 0.11445 (12) | 0.0354 (3) | |
O4 | 0.65823 (16) | −0.31769 (12) | 0.29326 (13) | 0.0387 (3) | |
C1 | 0.2436 (2) | 0.7719 (2) | 0.16999 (19) | 0.0382 (4) | |
H1 | 0.2748 | 0.8107 | 0.0839 | 0.046* | |
C2 | 0.1156 (2) | 0.8358 (2) | 0.2205 (2) | 0.0466 (5) | |
H2 | 0.0581 | 0.9147 | 0.1704 | 0.056* | |
C3 | 0.0737 (2) | 0.7794 (2) | 0.3487 (2) | 0.0423 (5) | |
H3 | −0.0130 | 0.8221 | 0.3865 | 0.051* | |
C4 | 0.1558 (2) | 0.66235 (19) | 0.42223 (18) | 0.0322 (4) | |
C5 | 0.28421 (19) | 0.59899 (18) | 0.35979 (16) | 0.0292 (4) | |
C6 | 0.1081 (2) | 0.6047 (2) | 0.55748 (18) | 0.0351 (4) | |
H6 | 0.1154 | 0.5100 | 0.5905 | 0.042* | |
C7 | 0.0551 (2) | 0.6840 (2) | 0.63386 (18) | 0.0351 (4) | |
H7 | 0.0687 | 0.7750 | 0.6017 | 0.042* | |
C8 | −0.02223 (19) | 0.64829 (19) | 0.76227 (17) | 0.0305 (4) | |
C9 | −0.0772 (2) | 0.5278 (2) | 0.81369 (19) | 0.0378 (4) | |
H9 | −0.0499 | 0.4569 | 0.7739 | 0.045* | |
C10 | −0.1717 (2) | 0.5126 (2) | 0.92315 (19) | 0.0374 (4) | |
H10 | −0.2075 | 0.4301 | 0.9564 | 0.045* | |
C11 | −0.1559 (2) | 0.7216 (2) | 0.93976 (19) | 0.0405 (4) | |
H11 | −0.1811 | 0.7890 | 0.9838 | 0.049* | |
C12 | −0.0591 (2) | 0.7437 (2) | 0.83136 (19) | 0.0395 (4) | |
H12 | −0.0182 | 0.8238 | 0.8044 | 0.047* | |
C13 | 0.61848 (18) | 0.15824 (16) | 0.25070 (15) | 0.0236 (3) | |
C14 | 0.65612 (18) | 0.12941 (17) | 0.37782 (16) | 0.0260 (3) | |
H14 | 0.6602 | 0.2015 | 0.4120 | 0.031* | |
C15 | 0.68768 (19) | −0.00338 (17) | 0.45486 (16) | 0.0275 (3) | |
C16 | 0.67891 (19) | −0.10810 (16) | 0.40280 (17) | 0.0272 (3) | |
H16 | 0.6998 | −0.1987 | 0.4537 | 0.033* | |
C17 | 0.63983 (18) | −0.08176 (16) | 0.27693 (16) | 0.0251 (3) | |
C18 | 0.60952 (19) | 0.05199 (16) | 0.20019 (16) | 0.0253 (3) | |
H18 | 0.5832 | 0.0704 | 0.1150 | 0.030* | |
C19 | 0.58834 (18) | 0.30377 (16) | 0.17058 (16) | 0.0249 (3) | |
C20 | 0.62541 (19) | −0.19701 (17) | 0.22521 (17) | 0.0283 (4) | |
C21 | 0.7299 (2) | −0.0319 (2) | 0.59072 (18) | 0.0405 (4) | |
H21A | 0.8344 | −0.0259 | 0.5903 | 0.061* | |
H21B | 0.7141 | −0.1226 | 0.6392 | 0.061* | |
H21C | 0.6684 | 0.0343 | 0.6305 | 0.061* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.03605 (8) | 0.01670 (6) | 0.02152 (7) | −0.00628 (4) | 0.00366 (5) | −0.00660 (5) |
N1 | 0.0355 (8) | 0.0292 (7) | 0.0250 (7) | −0.0070 (6) | 0.0046 (6) | −0.0078 (6) |
N2 | 0.0383 (8) | 0.0344 (8) | 0.0272 (7) | −0.0081 (7) | 0.0061 (6) | −0.0098 (7) |
N3 | 0.0447 (9) | 0.0355 (9) | 0.0287 (8) | 0.0013 (7) | 0.0082 (7) | −0.0041 (7) |
O1 | 0.0609 (9) | 0.0158 (5) | 0.0311 (7) | −0.0066 (5) | 0.0002 (6) | −0.0076 (5) |
O2 | 0.0543 (8) | 0.0298 (7) | 0.0252 (6) | −0.0072 (6) | −0.0068 (6) | −0.0021 (5) |
O3 | 0.0576 (8) | 0.0227 (6) | 0.0290 (7) | −0.0113 (6) | −0.0002 (6) | −0.0104 (5) |
O4 | 0.0586 (9) | 0.0175 (6) | 0.0405 (7) | −0.0049 (6) | −0.0067 (6) | −0.0087 (6) |
C1 | 0.0466 (11) | 0.0328 (10) | 0.0301 (9) | −0.0024 (8) | 0.0026 (8) | −0.0057 (8) |
C2 | 0.0501 (12) | 0.0403 (11) | 0.0387 (11) | 0.0089 (9) | −0.0032 (9) | −0.0059 (9) |
C3 | 0.0369 (10) | 0.0474 (12) | 0.0399 (11) | 0.0005 (9) | 0.0052 (8) | −0.0162 (9) |
C4 | 0.0296 (9) | 0.0366 (10) | 0.0325 (9) | −0.0085 (7) | 0.0045 (7) | −0.0137 (8) |
C5 | 0.0323 (9) | 0.0318 (9) | 0.0265 (8) | −0.0097 (7) | 0.0023 (7) | −0.0117 (7) |
C6 | 0.0328 (9) | 0.0398 (10) | 0.0324 (9) | −0.0085 (8) | 0.0047 (7) | −0.0104 (8) |
C7 | 0.0326 (9) | 0.0381 (10) | 0.0358 (10) | −0.0098 (8) | 0.0058 (8) | −0.0124 (8) |
C8 | 0.0270 (8) | 0.0348 (9) | 0.0295 (9) | −0.0069 (7) | 0.0008 (7) | −0.0087 (8) |
C9 | 0.0410 (10) | 0.0385 (10) | 0.0401 (10) | −0.0119 (8) | 0.0079 (8) | −0.0214 (9) |
C10 | 0.0424 (11) | 0.0343 (10) | 0.0388 (10) | −0.0142 (8) | 0.0091 (8) | −0.0146 (8) |
C11 | 0.0542 (12) | 0.0361 (10) | 0.0349 (10) | −0.0131 (9) | 0.0099 (9) | −0.0170 (9) |
C12 | 0.0509 (12) | 0.0348 (10) | 0.0354 (10) | −0.0151 (9) | 0.0074 (9) | −0.0124 (8) |
C13 | 0.0269 (8) | 0.0188 (7) | 0.0255 (8) | −0.0059 (6) | 0.0020 (6) | −0.0071 (6) |
C14 | 0.0305 (8) | 0.0226 (8) | 0.0276 (8) | −0.0059 (6) | −0.0004 (7) | −0.0108 (7) |
C15 | 0.0281 (8) | 0.0277 (8) | 0.0253 (8) | −0.0043 (7) | −0.0022 (7) | −0.0053 (7) |
C16 | 0.0305 (9) | 0.0183 (7) | 0.0300 (9) | −0.0032 (6) | −0.0012 (7) | −0.0032 (7) |
C17 | 0.0289 (8) | 0.0192 (7) | 0.0284 (8) | −0.0057 (6) | 0.0023 (6) | −0.0088 (7) |
C18 | 0.0336 (9) | 0.0204 (7) | 0.0227 (8) | −0.0066 (6) | 0.0026 (6) | −0.0074 (6) |
C19 | 0.0273 (8) | 0.0199 (7) | 0.0259 (8) | −0.0051 (6) | 0.0024 (6) | −0.0047 (7) |
C20 | 0.0336 (9) | 0.0205 (8) | 0.0321 (9) | −0.0077 (7) | 0.0061 (7) | −0.0105 (7) |
C21 | 0.0469 (11) | 0.0422 (11) | 0.0310 (10) | −0.0033 (9) | −0.0114 (8) | −0.0074 (9) |
Geometric parameters (Å, º) top
Cd1—O1 | 2.1974 (14) | C4—C6 | 1.467 (3) |
Cd1—O2i | 2.2959 (15) | C6—C7 | 1.324 (3) |
Cd1—O3ii | 2.3021 (13) | C6—H6 | 0.9400 |
Cd1—N2iii | 2.3464 (16) | C7—C8 | 1.469 (3) |
Cd1—N1 | 2.4133 (16) | C7—H7 | 0.9400 |
Cd1—O4ii | 2.4511 (14) | C8—C12 | 1.382 (3) |
Cd1—C20ii | 2.7110 (18) | C8—C9 | 1.387 (3) |
N1—C5 | 1.348 (2) | C9—C10 | 1.375 (3) |
N1—C1 | 1.351 (2) | C9—H9 | 0.9400 |
N2—C11 | 1.331 (2) | C10—H10 | 0.9400 |
N2—C10 | 1.339 (2) | C11—C12 | 1.380 (3) |
N2—Cd1iv | 2.3464 (16) | C11—H11 | 0.9400 |
N3—C5 | 1.340 (2) | C12—H12 | 0.9400 |
N3—H3A | 0.8700 | C13—C18 | 1.393 (2) |
N3—H3B | 0.8700 | C13—C14 | 1.395 (2) |
O1—C19 | 1.268 (2) | C13—C19 | 1.503 (2) |
O2—C19 | 1.240 (2) | C14—C15 | 1.387 (2) |
O2—Cd1i | 2.2959 (15) | C14—H14 | 0.9400 |
O3—C20 | 1.256 (2) | C15—C16 | 1.389 (2) |
O3—Cd1v | 2.3021 (13) | C15—C21 | 1.500 (2) |
O4—C20 | 1.257 (2) | C16—C17 | 1.390 (2) |
O4—Cd1v | 2.4511 (14) | C16—H16 | 0.9400 |
C1—C2 | 1.365 (3) | C17—C18 | 1.393 (2) |
C1—H1 | 0.9400 | C17—C20 | 1.502 (2) |
C2—C3 | 1.387 (3) | C18—H18 | 0.9400 |
C2—H2 | 0.9400 | C20—Cd1v | 2.7110 (18) |
C3—C4 | 1.377 (3) | C21—H21A | 0.9700 |
C3—H3 | 0.9400 | C21—H21B | 0.9700 |
C4—C5 | 1.428 (2) | C21—H21C | 0.9700 |
| | | |
O1—Cd1—O2i | 113.38 (6) | C6—C7—C8 | 128.47 (18) |
O1—Cd1—O3ii | 151.64 (5) | C6—C7—H7 | 115.8 |
O2i—Cd1—O3ii | 93.88 (6) | C8—C7—H7 | 115.8 |
O1—Cd1—N2iii | 100.32 (6) | C12—C8—C9 | 116.58 (17) |
O2i—Cd1—N2iii | 87.33 (6) | C12—C8—C7 | 119.68 (17) |
O3ii—Cd1—N2iii | 88.10 (6) | C9—C8—C7 | 123.30 (17) |
O1—Cd1—N1 | 90.89 (6) | C10—C9—C8 | 119.68 (18) |
O2i—Cd1—N1 | 84.47 (5) | C10—C9—H9 | 120.2 |
O3ii—Cd1—N1 | 83.84 (6) | C8—C9—H9 | 120.2 |
N2iii—Cd1—N1 | 168.07 (5) | N2—C10—C9 | 123.44 (18) |
O1—Cd1—O4ii | 96.69 (5) | N2—C10—H10 | 118.3 |
O2i—Cd1—O4ii | 147.58 (5) | C9—C10—H10 | 118.3 |
O3ii—Cd1—O4ii | 55.07 (5) | N2—C11—C12 | 123.02 (18) |
N2iii—Cd1—O4ii | 99.38 (6) | N2—C11—H11 | 118.5 |
N1—Cd1—O4ii | 83.18 (5) | C12—C11—H11 | 118.5 |
O1—Cd1—C20ii | 124.16 (5) | C11—C12—C8 | 120.19 (18) |
O2i—Cd1—C20ii | 120.63 (5) | C11—C12—H12 | 119.9 |
O3ii—Cd1—C20ii | 27.51 (5) | C8—C12—H12 | 119.9 |
N2iii—Cd1—C20ii | 95.37 (6) | C18—C13—C14 | 119.59 (15) |
N1—Cd1—C20ii | 81.47 (6) | C18—C13—C19 | 121.15 (15) |
O4ii—Cd1—C20ii | 27.61 (5) | C14—C13—C19 | 119.27 (14) |
C5—N1—C1 | 118.71 (16) | C15—C14—C13 | 121.42 (15) |
C5—N1—Cd1 | 128.47 (12) | C15—C14—H14 | 119.3 |
C1—N1—Cd1 | 111.45 (12) | C13—C14—H14 | 119.3 |
C11—N2—C10 | 116.83 (16) | C14—C15—C16 | 118.23 (15) |
C11—N2—Cd1iv | 119.51 (13) | C14—C15—C21 | 120.44 (16) |
C10—N2—Cd1iv | 121.47 (13) | C16—C15—C21 | 121.33 (16) |
C5—N3—H3A | 120.0 | C15—C16—C17 | 121.36 (15) |
C5—N3—H3B | 120.0 | C15—C16—H16 | 119.3 |
H3A—N3—H3B | 120.0 | C17—C16—H16 | 119.3 |
C19—O1—Cd1 | 121.91 (11) | C16—C17—C18 | 119.87 (15) |
C19—O2—Cd1i | 156.89 (13) | C16—C17—C20 | 120.03 (15) |
C20—O3—Cd1v | 94.68 (10) | C18—C17—C20 | 120.07 (15) |
C20—O4—Cd1v | 87.78 (11) | C13—C18—C17 | 119.52 (15) |
N1—C1—C2 | 123.83 (18) | C13—C18—H18 | 120.2 |
N1—C1—H1 | 118.1 | C17—C18—H18 | 120.2 |
C2—C1—H1 | 118.1 | O2—C19—O1 | 124.34 (15) |
C1—C2—C3 | 117.28 (19) | O2—C19—C13 | 119.49 (15) |
C1—C2—H2 | 121.4 | O1—C19—C13 | 116.12 (14) |
C3—C2—H2 | 121.4 | O3—C20—O4 | 122.26 (16) |
C4—C3—C2 | 121.76 (18) | O3—C20—C17 | 118.02 (15) |
C4—C3—H3 | 119.1 | O4—C20—C17 | 119.72 (16) |
C2—C3—H3 | 119.1 | O3—C20—Cd1v | 57.81 (9) |
C3—C4—C5 | 117.10 (17) | O4—C20—Cd1v | 64.61 (9) |
C3—C4—C6 | 120.45 (17) | C17—C20—Cd1v | 173.60 (12) |
C5—C4—C6 | 122.41 (17) | C15—C21—H21A | 109.5 |
N3—C5—N1 | 117.32 (16) | C15—C21—H21B | 109.5 |
N3—C5—C4 | 121.50 (16) | H21A—C21—H21B | 109.5 |
N1—C5—C4 | 121.18 (17) | C15—C21—H21C | 109.5 |
C7—C6—C4 | 121.10 (18) | H21A—C21—H21C | 109.5 |
C7—C6—H6 | 119.5 | H21B—C21—H21C | 109.5 |
C4—C6—H6 | 119.5 | | |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y+1, z; (iii) x+1, y, z−1; (iv) x−1, y, z+1; (v) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1 | 0.87 | 2.14 | 2.978 (2) | 161 |
N3—H3B···O4vi | 0.87 | 2.23 | 3.082 (2) | 165 |
Symmetry code: (vi) −x+1, −y, −z+1. |
Poly[[µ-
trans-1-(2-aminopyridin-3-yl)-2-(pyridin-4-yl)ethene-
κ2N:
N'](µ
2-5-hydroxyisophthalato-
κ4O1,
O1':
O3:
O5)cadmium(II)] (II)
top
Crystal data top
[Cd(C8H4O5)(C12H11N3)] | Dx = 1.787 Mg m−3 |
Mr = 489.76 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 64725 reflections |
a = 12.387 (3) Å | θ = 3.3–27.6° |
b = 14.684 (3) Å | µ = 1.24 mm−1 |
c = 20.016 (4) Å | T = 223 K |
V = 3640.7 (14) Å3 | Block, yellow |
Z = 8 | 0.18 × 0.15 × 0.11 mm |
F(000) = 1952 | |
Data collection top
Bruker SMART CCD area detector diffractometer | 3775 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
phi and ω scans | θmax = 27.6°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −16→16 |
Tmin = 0.853, Tmax = 0.921 | k = −19→18 |
64725 measured reflections | l = −25→25 |
4173 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.020 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.054 | w = 1/[σ2(Fo2) + (0.0257P)2 + 2.3943P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max = 0.005 |
4173 reflections | Δρmax = 0.36 e Å−3 |
266 parameters | Δρmin = −0.71 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 | |
Cd1 | 0.48864 (2) | 0.61822 (2) | 0.87458 (2) | 0.01753 (5) | |
N1 | 0.35402 (11) | 0.50694 (10) | 0.88858 (7) | 0.0227 (3) | |
N2 | −0.36006 (12) | 0.53178 (11) | 0.87845 (7) | 0.0254 (3) | |
N3 | 0.22766 (13) | 0.61335 (10) | 0.91990 (9) | 0.0329 (4) | |
H3A | 0.2801 | 0.6517 | 0.9264 | 0.039* | |
H3B | 0.1613 | 0.6300 | 0.9271 | 0.039* | |
O1 | 0.51172 (11) | 0.63091 (11) | 0.75542 (7) | 0.0401 (4) | |
O2 | 0.37207 (11) | 0.69117 (10) | 0.80604 (6) | 0.0317 (3) | |
O3 | 0.55494 (10) | 0.71467 (10) | 0.50613 (6) | 0.0371 (3) | |
O4 | 0.43607 (11) | 0.81688 (10) | 0.47007 (6) | 0.0379 (3) | |
O5 | 0.11421 (10) | 0.75300 (9) | 0.61704 (6) | 0.0259 (3) | |
H5 | 0.1012 (19) | 0.7673 (17) | 0.5792 (13) | 0.043 (7)* | |
C1 | 0.37896 (15) | 0.42128 (13) | 0.86961 (9) | 0.0293 (4) | |
H1 | 0.4521 | 0.4063 | 0.8635 | 0.035* | |
C2 | 0.30317 (16) | 0.35503 (14) | 0.85877 (12) | 0.0383 (5) | |
H2 | 0.3236 | 0.2961 | 0.8454 | 0.046* | |
C3 | 0.19511 (17) | 0.37743 (13) | 0.86804 (11) | 0.0360 (5) | |
H3 | 0.1416 | 0.3331 | 0.8608 | 0.043* | |
C4 | 0.16542 (13) | 0.46397 (12) | 0.88767 (9) | 0.0232 (3) | |
C5 | 0.24918 (13) | 0.52835 (11) | 0.89875 (8) | 0.0204 (3) | |
C6 | 0.05153 (13) | 0.48929 (12) | 0.89679 (9) | 0.0254 (3) | |
H6 | 0.0345 | 0.5323 | 0.9300 | 0.030* | |
C7 | −0.02907 (14) | 0.45450 (13) | 0.86047 (10) | 0.0272 (4) | |
H7 | −0.0113 | 0.4118 | 0.8273 | 0.033* | |
C8 | −0.14318 (13) | 0.47824 (12) | 0.86867 (9) | 0.0241 (3) | |
C9 | −0.18534 (14) | 0.51351 (13) | 0.92748 (9) | 0.0295 (4) | |
H9 | −0.1409 | 0.5202 | 0.9652 | 0.035* | |
C10 | −0.29258 (14) | 0.53881 (14) | 0.93044 (9) | 0.0308 (4) | |
H10 | −0.3195 | 0.5621 | 0.9709 | 0.037* | |
C11 | −0.32033 (14) | 0.49593 (13) | 0.82193 (10) | 0.0301 (4) | |
H11 | −0.3666 | 0.4899 | 0.7850 | 0.036* | |
C12 | −0.21491 (14) | 0.46754 (13) | 0.81560 (10) | 0.0315 (4) | |
H12 | −0.1913 | 0.4409 | 0.7755 | 0.038* | |
C13 | 0.37814 (13) | 0.70374 (11) | 0.68835 (7) | 0.0182 (3) | |
C14 | 0.26758 (13) | 0.71911 (11) | 0.68341 (7) | 0.0199 (3) | |
H14 | 0.2228 | 0.7119 | 0.7210 | 0.024* | |
C15 | 0.22424 (13) | 0.74512 (11) | 0.62254 (7) | 0.0194 (3) | |
C16 | 0.29080 (13) | 0.76130 (12) | 0.56827 (8) | 0.0231 (3) | |
H16 | 0.2612 | 0.7828 | 0.5280 | 0.028* | |
C17 | 0.40141 (13) | 0.74577 (11) | 0.57307 (8) | 0.0204 (3) | |
C18 | 0.44517 (13) | 0.71487 (11) | 0.63301 (7) | 0.0191 (3) | |
H18 | 0.5192 | 0.7016 | 0.6361 | 0.023* | |
C19 | 0.42451 (13) | 0.67335 (11) | 0.75376 (8) | 0.0206 (3) | |
C20 | 0.47056 (13) | 0.76013 (13) | 0.51226 (8) | 0.0233 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.01361 (7) | 0.02614 (8) | 0.01285 (7) | 0.00256 (4) | −0.00130 (4) | −0.00154 (4) |
N1 | 0.0147 (6) | 0.0257 (7) | 0.0278 (7) | 0.0013 (5) | 0.0010 (5) | −0.0010 (6) |
N2 | 0.0167 (7) | 0.0321 (8) | 0.0273 (7) | 0.0034 (6) | −0.0017 (5) | 0.0028 (6) |
N3 | 0.0156 (7) | 0.0303 (8) | 0.0529 (11) | −0.0029 (6) | 0.0066 (7) | −0.0161 (7) |
O1 | 0.0307 (7) | 0.0701 (11) | 0.0194 (7) | 0.0227 (7) | −0.0040 (5) | 0.0029 (7) |
O2 | 0.0349 (7) | 0.0466 (8) | 0.0137 (5) | 0.0142 (6) | −0.0001 (5) | 0.0032 (5) |
O3 | 0.0222 (6) | 0.0615 (9) | 0.0276 (7) | 0.0154 (6) | 0.0085 (5) | 0.0186 (6) |
O4 | 0.0265 (7) | 0.0602 (9) | 0.0270 (7) | 0.0146 (6) | 0.0100 (5) | 0.0250 (6) |
O5 | 0.0130 (6) | 0.0417 (8) | 0.0230 (6) | 0.0012 (5) | −0.0005 (4) | 0.0095 (5) |
C1 | 0.0182 (8) | 0.0273 (9) | 0.0423 (11) | 0.0064 (7) | 0.0013 (7) | 0.0005 (8) |
C2 | 0.0267 (10) | 0.0225 (9) | 0.0657 (14) | 0.0064 (8) | −0.0015 (9) | −0.0053 (9) |
C3 | 0.0226 (10) | 0.0237 (9) | 0.0618 (14) | −0.0009 (7) | −0.0047 (9) | −0.0026 (8) |
C4 | 0.0155 (7) | 0.0241 (8) | 0.0301 (9) | 0.0010 (6) | −0.0023 (6) | 0.0012 (7) |
C5 | 0.0154 (7) | 0.0250 (8) | 0.0209 (7) | 0.0018 (6) | 0.0006 (6) | −0.0003 (6) |
C6 | 0.0163 (8) | 0.0251 (8) | 0.0347 (9) | 0.0002 (7) | 0.0006 (7) | 0.0022 (7) |
C7 | 0.0173 (8) | 0.0274 (9) | 0.0368 (10) | 0.0013 (7) | 0.0005 (7) | −0.0009 (7) |
C8 | 0.0152 (8) | 0.0217 (8) | 0.0352 (9) | −0.0011 (6) | −0.0018 (6) | 0.0030 (7) |
C9 | 0.0192 (8) | 0.0434 (11) | 0.0259 (9) | 0.0023 (7) | −0.0043 (7) | 0.0061 (8) |
C10 | 0.0222 (8) | 0.0468 (11) | 0.0233 (9) | 0.0068 (8) | 0.0006 (7) | 0.0047 (8) |
C11 | 0.0204 (8) | 0.0363 (10) | 0.0337 (10) | 0.0039 (7) | −0.0076 (7) | −0.0089 (8) |
C12 | 0.0211 (8) | 0.0378 (10) | 0.0355 (10) | 0.0043 (7) | −0.0021 (7) | −0.0124 (8) |
C13 | 0.0188 (7) | 0.0216 (7) | 0.0142 (7) | 0.0002 (6) | −0.0025 (6) | 0.0012 (6) |
C14 | 0.0181 (7) | 0.0266 (8) | 0.0151 (7) | −0.0006 (6) | 0.0019 (6) | 0.0010 (6) |
C15 | 0.0131 (7) | 0.0264 (8) | 0.0186 (8) | 0.0007 (6) | −0.0009 (5) | 0.0022 (6) |
C16 | 0.0173 (7) | 0.0357 (9) | 0.0164 (7) | 0.0012 (7) | −0.0015 (6) | 0.0080 (7) |
C17 | 0.0173 (7) | 0.0278 (8) | 0.0160 (7) | 0.0000 (6) | 0.0008 (6) | 0.0043 (6) |
C18 | 0.0137 (7) | 0.0253 (8) | 0.0183 (7) | −0.0005 (6) | −0.0015 (5) | 0.0020 (6) |
C19 | 0.0211 (8) | 0.0239 (7) | 0.0168 (7) | −0.0016 (6) | −0.0044 (6) | 0.0007 (6) |
C20 | 0.0161 (7) | 0.0369 (9) | 0.0167 (8) | −0.0001 (7) | 0.0005 (6) | 0.0058 (7) |
Geometric parameters (Å, º) top
Cd1—O4i | 2.2329 (12) | C3—C4 | 1.380 (3) |
Cd1—O2 | 2.2614 (12) | C3—H3 | 0.9400 |
Cd1—N2ii | 2.2649 (15) | C4—C5 | 1.421 (2) |
Cd1—N1 | 2.3513 (15) | C4—C6 | 1.470 (2) |
Cd1—O1 | 2.4094 (15) | C6—C7 | 1.337 (3) |
Cd1—O5iii | 2.5229 (14) | C6—H6 | 0.9400 |
Cd1—C19 | 2.6709 (16) | C7—C8 | 1.465 (2) |
N1—C1 | 1.350 (2) | C7—H7 | 0.9400 |
N1—C5 | 1.352 (2) | C8—C9 | 1.388 (3) |
N2—C10 | 1.339 (2) | C8—C12 | 1.394 (2) |
N2—C11 | 1.341 (2) | C9—C10 | 1.381 (2) |
N2—Cd1iv | 2.2650 (15) | C9—H9 | 0.9400 |
N3—C5 | 1.345 (2) | C10—H10 | 0.9400 |
N3—H3A | 0.8700 | C11—C12 | 1.377 (2) |
N3—H3B | 0.8700 | C11—H11 | 0.9400 |
O1—C19 | 1.248 (2) | C12—H12 | 0.9400 |
O2—C19 | 1.259 (2) | C13—C14 | 1.392 (2) |
O3—C20 | 1.246 (2) | C13—C18 | 1.394 (2) |
O4—C20 | 1.261 (2) | C13—C19 | 1.498 (2) |
O4—Cd1v | 2.2330 (12) | C14—C15 | 1.385 (2) |
O5—C15 | 1.3723 (19) | C14—H14 | 0.9400 |
O5—Cd1vi | 2.5229 (14) | C15—C16 | 1.384 (2) |
O5—H5 | 0.80 (3) | C16—C17 | 1.392 (2) |
C1—C2 | 1.369 (3) | C16—H16 | 0.9400 |
C1—H1 | 0.9400 | C17—C18 | 1.392 (2) |
C2—C3 | 1.391 (3) | C17—C20 | 1.503 (2) |
C2—H2 | 0.9400 | C18—H18 | 0.9400 |
| | | |
O4i—Cd1—O2 | 97.52 (5) | N1—C5—C4 | 121.56 (15) |
O4i—Cd1—N2ii | 116.82 (5) | C7—C6—C4 | 123.55 (18) |
O2—Cd1—N2ii | 144.55 (5) | C7—C6—H6 | 118.2 |
O4i—Cd1—N1 | 89.30 (5) | C4—C6—H6 | 118.2 |
O2—Cd1—N1 | 87.06 (5) | C6—C7—C8 | 124.67 (18) |
N2ii—Cd1—N1 | 101.15 (6) | C6—C7—H7 | 117.7 |
O4i—Cd1—O1 | 148.10 (6) | C8—C7—H7 | 117.7 |
O2—Cd1—O1 | 55.85 (4) | C9—C8—C12 | 116.65 (16) |
N2ii—Cd1—O1 | 88.80 (5) | C9—C8—C7 | 123.15 (16) |
N1—Cd1—O1 | 104.83 (5) | C12—C8—C7 | 120.19 (17) |
O4i—Cd1—O5iii | 77.76 (5) | C10—C9—C8 | 119.93 (17) |
O2—Cd1—O5iii | 93.58 (5) | C10—C9—H9 | 120.0 |
N2ii—Cd1—O5iii | 85.82 (5) | C8—C9—H9 | 120.0 |
N1—Cd1—O5iii | 167.02 (5) | N2—C10—C9 | 123.13 (18) |
O1—Cd1—O5iii | 86.10 (5) | N2—C10—H10 | 118.4 |
O4i—Cd1—C19 | 123.98 (6) | C9—C10—H10 | 118.4 |
O2—Cd1—C19 | 28.04 (5) | N2—C11—C12 | 123.00 (17) |
N2ii—Cd1—C19 | 116.55 (5) | N2—C11—H11 | 118.5 |
N1—Cd1—C19 | 96.18 (5) | C12—C11—H11 | 118.5 |
O1—Cd1—C19 | 27.83 (5) | C11—C12—C8 | 120.03 (17) |
O5iii—Cd1—C19 | 90.33 (5) | C11—C12—H12 | 120.0 |
C1—N1—C5 | 118.62 (15) | C8—C12—H12 | 120.0 |
C1—N1—Cd1 | 116.86 (11) | C14—C13—C18 | 120.72 (14) |
C5—N1—Cd1 | 122.53 (11) | C14—C13—C19 | 119.20 (14) |
C10—N2—C11 | 117.18 (15) | C18—C13—C19 | 120.07 (14) |
C10—N2—Cd1iv | 120.00 (12) | C15—C14—C13 | 119.25 (14) |
C11—N2—Cd1iv | 119.65 (11) | C15—C14—H14 | 120.4 |
C5—N3—H3A | 120.0 | C13—C14—H14 | 120.4 |
C5—N3—H3B | 120.0 | O5—C15—C16 | 120.94 (14) |
H3A—N3—H3B | 120.0 | O5—C15—C14 | 118.60 (14) |
C19—O1—Cd1 | 87.83 (10) | C16—C15—C14 | 120.45 (15) |
C19—O2—Cd1 | 94.38 (10) | C15—C16—C17 | 120.25 (15) |
C20—O4—Cd1v | 139.16 (11) | C15—C16—H16 | 119.9 |
C15—O5—Cd1vi | 122.75 (11) | C17—C16—H16 | 119.9 |
C15—O5—H5 | 107.3 (17) | C16—C17—C18 | 119.73 (14) |
Cd1vi—O5—H5 | 98.3 (17) | C16—C17—C20 | 118.81 (14) |
N1—C1—C2 | 123.35 (17) | C18—C17—C20 | 121.43 (14) |
N1—C1—H1 | 118.3 | C17—C18—C13 | 119.40 (15) |
C2—C1—H1 | 118.3 | C17—C18—H18 | 120.3 |
C1—C2—C3 | 118.09 (18) | C13—C18—H18 | 120.3 |
C1—C2—H2 | 121.0 | O1—C19—O2 | 121.90 (15) |
C3—C2—H2 | 121.0 | O1—C19—C13 | 120.27 (15) |
C4—C3—C2 | 120.81 (18) | O2—C19—C13 | 117.82 (14) |
C4—C3—H3 | 119.6 | O1—C19—Cd1 | 64.35 (9) |
C2—C3—H3 | 119.6 | O2—C19—Cd1 | 57.59 (8) |
C3—C4—C5 | 117.55 (16) | C13—C19—Cd1 | 174.74 (11) |
C3—C4—C6 | 121.59 (16) | O3—C20—O4 | 124.91 (15) |
C5—C4—C6 | 120.86 (15) | O3—C20—C17 | 118.85 (15) |
N3—C5—N1 | 116.98 (15) | O4—C20—C17 | 116.22 (14) |
N3—C5—C4 | 121.46 (15) | | |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y, −z+3/2; (iv) x−1, y, z; (v) x, −y+3/2, z−1/2; (vi) x−1/2, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4i | 0.87 | 2.17 | 2.954 (2) | 150 |
N3—H3B···O3vi | 0.87 | 2.25 | 2.997 (2) | 144 |
O5—H5···O3vii | 0.80 (3) | 1.82 (3) | 2.6159 (18) | 171 (2) |
Symmetry codes: (i) x, −y+3/2, z+1/2; (vi) x−1/2, y, −z+3/2; (vii) x−1/2, −y+3/2, −z+1. |
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