A novel supramolecular framework,
catena-poly[[[aqua(2-phenylquinoline-4-carboxylato-
O)silver(I)]-
-4,4'-bipyridine-
2N:
N'] dihydrate], {[Ag(C
16H
10NO
2)(C
10H
8N
2)(H
2O)]·2H
2O}
n, has been synthesized and structurally characterized. The Ag
I centres are four-coordinated and bridged by 4,4'-bipyridine (4,4'-bipy) ligands to form a one-dimensional Ag-bipy chain. The Ag-bipy chains are further linked together by intermolecular O-H
O and O-H
N hydrogen-bonding interactions between adjacent chains, resulting in a three-dimensional framework.
Supporting information
CCDC reference: 809802
To a mixture of HL (24.9 mg, 0.1 mmol) and NaOH (4.0 mg, 0.1 mmol) in
water was added AgNO3 (17.0 mg, 0.1 mmol) with constant stirring, followed
by 4,4'-bipy (15.6 mg, 0.1 mmol) in water. After the sample had been stirred
for 30 min, the precipitate which formed was dissolved by dropwise addition of
aqueous NH3 solution. Colourless block-shaped crystals of (I) were obtained
from the filtrate by slow evaporation after standing in the dark for several
days (yield 50%).
H atoms were placed in idealized positions and allowed to ride on their parent
C atoms, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C). The
water H atoms were located in a difference Fourier map and refined with a
restraint of O—H = 0.84 (1) Å. They were refined as riding atoms in the
final refinement, with Uiso(H) = 1.5Ueq(O).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
catena-Poly[[[aqua(2-phenylquinoline-4-carboxylato-
κO)silver(I)]-µ-4,4'-bipyridine-
κ2N:
N'] dihydrate]
top
Crystal data top
[Ag(C16H10NO2)(C10H8N2)(H2O)]·2H2O | F(000) = 1152 |
Mr = 566.35 | Dx = 1.590 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 4054 reflections |
a = 9.4006 (9) Å | θ = 2.3–26.0° |
b = 27.461 (3) Å | µ = 0.90 mm−1 |
c = 9.5349 (9) Å | T = 151 K |
β = 105.987 (1)° | Block, colourless |
V = 2366.3 (4) Å3 | 0.28 × 0.22 × 0.15 mm |
Z = 4 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 4645 independent reflections |
Radiation source: fine-focus sealed tube | 3708 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −11→11 |
Tmin = 0.788, Tmax = 0.877 | k = −27→33 |
13019 measured reflections | l = −10→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.3783P] where P = (Fo2 + 2Fc2)/3 |
4645 reflections | (Δ/σ)max < 0.001 |
316 parameters | Δρmax = 0.98 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
Crystal data top
[Ag(C16H10NO2)(C10H8N2)(H2O)]·2H2O | V = 2366.3 (4) Å3 |
Mr = 566.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.4006 (9) Å | µ = 0.90 mm−1 |
b = 27.461 (3) Å | T = 151 K |
c = 9.5349 (9) Å | 0.28 × 0.22 × 0.15 mm |
β = 105.987 (1)° | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 4645 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 3708 reflections with I > 2σ(I) |
Tmin = 0.788, Tmax = 0.877 | Rint = 0.036 |
13019 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.98 e Å−3 |
4645 reflections | Δρmin = −0.42 e Å−3 |
316 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.6613 (3) | 0.12837 (11) | 0.4701 (3) | 0.0256 (6) | |
C2 | 0.6926 (3) | 0.17228 (11) | 0.4059 (3) | 0.0258 (6) | |
C3 | 0.8314 (3) | 0.19522 (11) | 0.4725 (3) | 0.0264 (7) | |
C4 | 0.8992 (3) | 0.13549 (10) | 0.6497 (3) | 0.0240 (6) | |
C5 | 0.7634 (3) | 0.11086 (11) | 0.5910 (3) | 0.0260 (6) | |
H5 | 0.7430 | 0.0818 | 0.6362 | 0.031* | |
C6 | 0.5151 (3) | 0.10155 (12) | 0.4104 (3) | 0.0298 (7) | |
C7 | 0.5962 (3) | 0.19405 (12) | 0.2805 (3) | 0.0316 (7) | |
H7 | 0.5060 | 0.1783 | 0.2324 | 0.038* | |
C8 | 0.6315 (4) | 0.23733 (12) | 0.2281 (4) | 0.0365 (8) | |
H8 | 0.5655 | 0.2517 | 0.1447 | 0.044* | |
C9 | 0.7653 (4) | 0.26060 (13) | 0.2976 (4) | 0.0389 (8) | |
H9 | 0.7881 | 0.2911 | 0.2619 | 0.047* | |
C10 | 0.8631 (4) | 0.24003 (12) | 0.4154 (4) | 0.0356 (8) | |
H10 | 0.9538 | 0.2561 | 0.4598 | 0.043* | |
C11 | 1.0075 (3) | 0.11691 (12) | 0.7843 (3) | 0.0276 (7) | |
C12 | 1.0138 (3) | 0.06776 (13) | 0.8220 (4) | 0.0356 (8) | |
H12 | 0.9505 | 0.0451 | 0.7594 | 0.043* | |
C13 | 1.1123 (4) | 0.05178 (14) | 0.9506 (4) | 0.0427 (9) | |
H13 | 1.1158 | 0.0182 | 0.9750 | 0.051* | |
C14 | 1.2051 (4) | 0.08406 (15) | 1.0435 (4) | 0.0436 (9) | |
H14 | 1.2720 | 0.0729 | 1.1315 | 0.052* | |
C15 | 1.1996 (3) | 0.13277 (15) | 1.0068 (3) | 0.0394 (8) | |
H15 | 1.2634 | 0.1552 | 1.0701 | 0.047* | |
C16 | 1.1028 (3) | 0.14938 (13) | 0.8796 (3) | 0.0322 (7) | |
H16 | 1.1005 | 0.1830 | 0.8561 | 0.039* | |
C17 | −0.0046 (3) | 0.13603 (12) | 0.2579 (3) | 0.0309 (7) | |
H17 | 0.0636 | 0.1623 | 0.2743 | 0.037* | |
C18 | −0.1241 (3) | 0.13736 (12) | 0.1351 (3) | 0.0315 (7) | |
H18 | −0.1374 | 0.1643 | 0.0702 | 0.038* | |
C19 | −0.2250 (3) | 0.09890 (12) | 0.1071 (3) | 0.0282 (7) | |
C20 | −0.1989 (3) | 0.06115 (12) | 0.2080 (3) | 0.0337 (7) | |
H20 | −0.2645 | 0.0342 | 0.1942 | 0.040* | |
C21 | −0.0781 (4) | 0.06300 (12) | 0.3276 (3) | 0.0361 (8) | |
H21 | −0.0628 | 0.0368 | 0.3952 | 0.043* | |
C22 | −0.5273 (4) | 0.05631 (12) | −0.2163 (3) | 0.0358 (8) | |
H22 | −0.5607 | 0.0265 | −0.2646 | 0.043* | |
C23 | −0.4070 (3) | 0.05535 (12) | −0.0952 (3) | 0.0345 (7) | |
H23 | −0.3603 | 0.0253 | −0.0607 | 0.041* | |
C24 | −0.3538 (3) | 0.09850 (12) | −0.0234 (3) | 0.0292 (7) | |
C25 | −0.4279 (3) | 0.14116 (12) | −0.0803 (3) | 0.0331 (7) | |
H25 | −0.3950 | 0.1717 | −0.0363 | 0.040* | |
C26 | −0.5487 (3) | 0.13882 (13) | −0.2002 (3) | 0.0341 (7) | |
H26 | −0.5986 | 0.1683 | −0.2358 | 0.041* | |
N1 | 0.0200 (3) | 0.09981 (9) | 0.3546 (3) | 0.0287 (6) | |
N2 | −0.6000 (3) | 0.09750 (10) | −0.2698 (3) | 0.0328 (6) | |
N3 | 0.9327 (3) | 0.17626 (9) | 0.5915 (3) | 0.0265 (6) | |
O1 | 0.3988 (2) | 0.12609 (8) | 0.3870 (2) | 0.0358 (5) | |
O2 | 0.5224 (2) | 0.05672 (8) | 0.3900 (3) | 0.0398 (6) | |
O1W | 0.2746 (2) | 0.00869 (9) | 0.4363 (3) | 0.0461 (6) | |
H1A | 0.3308 | 0.0250 | 0.3982 | 0.069* | |
H1B | 0.3277 | −0.0112 | 0.4968 | 0.069* | |
O2W | 1.2085 (3) | 0.23329 (9) | 0.6600 (2) | 0.0475 (7) | |
H2A | 1.1397 | 0.2129 | 0.6506 | 0.071* | |
H2B | 1.2376 | 0.2340 | 0.5843 | 0.071* | |
O3W | 0.3189 (3) | 0.22196 (10) | 0.4276 (3) | 0.0539 (7) | |
H3A | 0.2826 | 0.2330 | 0.3420 | 0.081* | |
H3B | 0.3271 | 0.1912 | 0.4218 | 0.081* | |
Ag1 | 0.21896 (2) | 0.096573 (10) | 0.53296 (3) | 0.03692 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0251 (15) | 0.0253 (17) | 0.0278 (15) | 0.0003 (12) | 0.0096 (13) | −0.0026 (13) |
C2 | 0.0255 (15) | 0.0299 (17) | 0.0235 (15) | 0.0015 (13) | 0.0093 (12) | −0.0003 (13) |
C3 | 0.0274 (15) | 0.0302 (17) | 0.0255 (15) | −0.0019 (13) | 0.0139 (13) | −0.0009 (13) |
C4 | 0.0240 (15) | 0.0239 (16) | 0.0253 (15) | 0.0007 (12) | 0.0086 (12) | −0.0041 (12) |
C5 | 0.0251 (15) | 0.0246 (16) | 0.0290 (16) | −0.0008 (12) | 0.0084 (13) | −0.0006 (13) |
C6 | 0.0245 (16) | 0.038 (2) | 0.0253 (16) | −0.0043 (14) | 0.0040 (13) | 0.0055 (14) |
C7 | 0.0267 (16) | 0.040 (2) | 0.0288 (16) | 0.0002 (14) | 0.0096 (13) | 0.0020 (14) |
C8 | 0.0373 (19) | 0.043 (2) | 0.0291 (17) | 0.0072 (15) | 0.0099 (15) | 0.0130 (15) |
C9 | 0.042 (2) | 0.035 (2) | 0.044 (2) | −0.0054 (15) | 0.0183 (17) | 0.0078 (15) |
C10 | 0.0341 (18) | 0.037 (2) | 0.0385 (19) | −0.0083 (14) | 0.0146 (15) | 0.0004 (15) |
C11 | 0.0212 (15) | 0.0352 (18) | 0.0267 (16) | 0.0014 (13) | 0.0071 (12) | −0.0027 (13) |
C12 | 0.0264 (17) | 0.040 (2) | 0.0369 (18) | 0.0004 (14) | 0.0033 (14) | −0.0027 (15) |
C13 | 0.0359 (19) | 0.046 (2) | 0.043 (2) | 0.0093 (16) | 0.0052 (16) | 0.0116 (17) |
C14 | 0.0291 (19) | 0.066 (3) | 0.0312 (19) | 0.0079 (17) | 0.0014 (15) | 0.0045 (17) |
C15 | 0.0238 (17) | 0.059 (3) | 0.0319 (18) | −0.0049 (15) | 0.0022 (14) | −0.0064 (16) |
C16 | 0.0257 (16) | 0.0400 (19) | 0.0329 (17) | −0.0023 (14) | 0.0116 (14) | −0.0047 (15) |
C17 | 0.0214 (15) | 0.0391 (19) | 0.0302 (17) | −0.0013 (13) | 0.0035 (13) | −0.0043 (14) |
C18 | 0.0234 (16) | 0.041 (2) | 0.0284 (16) | 0.0007 (14) | 0.0031 (13) | 0.0007 (14) |
C19 | 0.0188 (14) | 0.0425 (19) | 0.0223 (15) | 0.0040 (13) | 0.0037 (12) | −0.0019 (14) |
C20 | 0.0278 (17) | 0.0357 (19) | 0.0330 (17) | −0.0045 (14) | 0.0004 (14) | 0.0014 (14) |
C21 | 0.0325 (18) | 0.039 (2) | 0.0308 (17) | 0.0014 (15) | −0.0005 (14) | 0.0049 (15) |
C22 | 0.0307 (17) | 0.038 (2) | 0.0324 (18) | −0.0047 (15) | −0.0015 (14) | −0.0062 (15) |
C23 | 0.0273 (17) | 0.0359 (19) | 0.0339 (17) | 0.0022 (14) | −0.0025 (14) | 0.0000 (15) |
C24 | 0.0190 (15) | 0.043 (2) | 0.0247 (15) | 0.0018 (13) | 0.0047 (12) | −0.0014 (14) |
C25 | 0.0273 (17) | 0.038 (2) | 0.0303 (17) | 0.0002 (14) | 0.0022 (13) | −0.0033 (14) |
C26 | 0.0258 (16) | 0.041 (2) | 0.0312 (17) | 0.0071 (14) | 0.0011 (14) | 0.0015 (15) |
N1 | 0.0204 (13) | 0.0393 (16) | 0.0242 (13) | 0.0027 (11) | 0.0026 (10) | −0.0042 (12) |
N2 | 0.0213 (13) | 0.0478 (18) | 0.0256 (14) | 0.0007 (12) | 0.0005 (11) | 0.0008 (12) |
N3 | 0.0234 (13) | 0.0302 (15) | 0.0270 (13) | −0.0020 (11) | 0.0091 (11) | −0.0039 (11) |
O1 | 0.0198 (11) | 0.0412 (14) | 0.0444 (13) | −0.0007 (10) | 0.0056 (10) | 0.0095 (11) |
O2 | 0.0318 (13) | 0.0314 (14) | 0.0513 (15) | −0.0066 (10) | 0.0029 (11) | −0.0004 (11) |
O1W | 0.0322 (13) | 0.0349 (14) | 0.0662 (17) | −0.0023 (10) | 0.0051 (12) | −0.0001 (12) |
O2W | 0.0381 (14) | 0.0678 (18) | 0.0368 (14) | −0.0187 (12) | 0.0109 (11) | −0.0052 (12) |
O3W | 0.0636 (18) | 0.0591 (18) | 0.0439 (15) | 0.0132 (14) | 0.0230 (14) | 0.0070 (13) |
Ag1 | 0.01974 (14) | 0.0574 (2) | 0.02758 (15) | 0.00090 (11) | −0.00367 (10) | 0.00003 (12) |
Geometric parameters (Å, º) top
C1—C5 | 1.369 (4) | C17—N1 | 1.332 (4) |
C1—C2 | 1.419 (4) | C17—C18 | 1.381 (4) |
C1—C6 | 1.525 (4) | C17—H17 | 0.9500 |
C2—C7 | 1.418 (4) | C18—C19 | 1.395 (4) |
C2—C3 | 1.431 (4) | C18—H18 | 0.9500 |
C3—N3 | 1.368 (4) | C19—C20 | 1.389 (4) |
C3—C10 | 1.410 (4) | C19—C24 | 1.478 (4) |
C4—N3 | 1.326 (4) | C20—C21 | 1.371 (4) |
C4—C5 | 1.417 (4) | C20—H20 | 0.9500 |
C4—C11 | 1.491 (4) | C21—N1 | 1.344 (4) |
C5—H5 | 0.9500 | C21—H21 | 0.9500 |
C6—O1 | 1.251 (4) | C22—N2 | 1.347 (4) |
C6—O2 | 1.251 (4) | C22—C23 | 1.377 (4) |
C7—C8 | 1.365 (4) | C22—H22 | 0.9500 |
C7—H7 | 0.9500 | C23—C24 | 1.391 (4) |
C8—C9 | 1.404 (5) | C23—H23 | 0.9500 |
C8—H8 | 0.9500 | C24—C25 | 1.394 (4) |
C9—C10 | 1.363 (5) | C25—C26 | 1.373 (4) |
C9—H9 | 0.9500 | C25—H25 | 0.9500 |
C10—H10 | 0.9500 | C26—N2 | 1.336 (4) |
C11—C12 | 1.393 (5) | C26—H26 | 0.9500 |
C11—C16 | 1.405 (4) | Ag1—N1 | 2.156 (2) |
C12—C13 | 1.389 (4) | Ag1—N2i | 2.161 (3) |
C12—H12 | 0.9500 | Ag1—O1 | 2.598 (2) |
C13—C14 | 1.381 (5) | Ag1—O1W | 2.685 (2) |
C13—H13 | 0.9500 | O1W—H1A | 0.8476 |
C14—C15 | 1.380 (6) | O1W—H1B | 0.8494 |
C14—H14 | 0.9500 | O2W—H2A | 0.8418 |
C15—C16 | 1.378 (4) | O2W—H2B | 0.8391 |
C15—H15 | 0.9500 | O3W—H3A | 0.8496 |
C16—H16 | 0.9500 | O3W—H3B | 0.8504 |
| | | |
C5—C1—C2 | 118.8 (3) | N1—C17—H17 | 118.3 |
C5—C1—C6 | 119.7 (3) | C18—C17—H17 | 118.3 |
C2—C1—C6 | 121.5 (3) | C17—C18—C19 | 119.6 (3) |
C7—C2—C1 | 124.2 (3) | C17—C18—H18 | 120.2 |
C7—C2—C3 | 118.8 (3) | C19—C18—H18 | 120.2 |
C1—C2—C3 | 117.1 (3) | C20—C19—C18 | 116.8 (3) |
N3—C3—C10 | 118.7 (3) | C20—C19—C24 | 121.6 (3) |
N3—C3—C2 | 122.8 (3) | C18—C19—C24 | 121.5 (3) |
C10—C3—C2 | 118.5 (3) | C21—C20—C19 | 119.7 (3) |
N3—C4—C5 | 122.0 (3) | C21—C20—H20 | 120.1 |
N3—C4—C11 | 117.7 (3) | C19—C20—H20 | 120.1 |
C5—C4—C11 | 120.2 (3) | N1—C21—C20 | 123.7 (3) |
C1—C5—C4 | 120.8 (3) | N1—C21—H21 | 118.2 |
C1—C5—H5 | 119.6 | C20—C21—H21 | 118.2 |
C4—C5—H5 | 119.6 | N2—C22—C23 | 123.2 (3) |
O1—C6—O2 | 125.8 (3) | N2—C22—H22 | 118.4 |
O1—C6—C1 | 117.4 (3) | C23—C22—H22 | 118.4 |
O2—C6—C1 | 116.8 (3) | C22—C23—C24 | 119.8 (3) |
C8—C7—C2 | 120.8 (3) | C22—C23—H23 | 120.1 |
C8—C7—H7 | 119.6 | C24—C23—H23 | 120.1 |
C2—C7—H7 | 119.6 | C23—C24—C25 | 116.8 (3) |
C7—C8—C9 | 120.0 (3) | C23—C24—C19 | 121.4 (3) |
C7—C8—H8 | 120.0 | C25—C24—C19 | 121.8 (3) |
C9—C8—H8 | 120.0 | C26—C25—C24 | 119.6 (3) |
C10—C9—C8 | 120.9 (3) | C26—C25—H25 | 120.2 |
C10—C9—H9 | 119.6 | C24—C25—H25 | 120.2 |
C8—C9—H9 | 119.6 | N2—C26—C25 | 123.8 (3) |
C9—C10—C3 | 120.9 (3) | N2—C26—H26 | 118.1 |
C9—C10—H10 | 119.5 | C25—C26—H26 | 118.1 |
C3—C10—H10 | 119.5 | C17—N1—C21 | 116.7 (3) |
C12—C11—C16 | 118.3 (3) | C17—N1—Ag1 | 121.6 (2) |
C12—C11—C4 | 121.6 (3) | C21—N1—Ag1 | 121.3 (2) |
C16—C11—C4 | 120.1 (3) | C26—N2—C22 | 116.7 (3) |
C13—C12—C11 | 120.3 (3) | C26—N2—Ag1i | 122.2 (2) |
C13—C12—H12 | 119.9 | C22—N2—Ag1i | 121.0 (2) |
C11—C12—H12 | 119.9 | C4—N3—C3 | 118.5 (2) |
C14—C13—C12 | 120.9 (3) | C6—O1—Ag1 | 113.70 (19) |
C14—C13—H13 | 119.6 | Ag1—O1W—H1A | 82.8 |
C12—C13—H13 | 119.6 | Ag1—O1W—H1B | 118.6 |
C15—C14—C13 | 119.1 (3) | H1A—O1W—H1B | 108.2 |
C15—C14—H14 | 120.4 | H2A—O2W—H2B | 110.3 |
C13—C14—H14 | 120.4 | H3A—O3W—H3B | 108.1 |
C16—C15—C14 | 120.9 (3) | N1—Ag1—N2ii | 172.00 (9) |
C16—C15—H15 | 119.5 | N1—Ag1—O1 | 96.64 (8) |
C14—C15—H15 | 119.5 | N2ii—Ag1—O1 | 89.43 (8) |
C15—C16—C11 | 120.5 (3) | N1—Ag1—O1W | 88.57 (8) |
C15—C16—H16 | 119.7 | N2ii—Ag1—O1W | 97.36 (9) |
C11—C16—H16 | 119.7 | O1—Ag1—O1W | 83.08 (8) |
N1—C17—C18 | 123.5 (3) | | |
| | | |
C5—C1—C2—C7 | 179.9 (3) | C17—C18—C19—C20 | 0.8 (4) |
C6—C1—C2—C7 | −2.2 (4) | C17—C18—C19—C24 | −179.5 (3) |
C5—C1—C2—C3 | 0.6 (4) | C18—C19—C20—C21 | −0.2 (5) |
C6—C1—C2—C3 | 178.5 (3) | C24—C19—C20—C21 | −180.0 (3) |
C7—C2—C3—N3 | −178.4 (3) | C19—C20—C21—N1 | −0.2 (5) |
C1—C2—C3—N3 | 0.9 (4) | N2—C22—C23—C24 | −1.0 (5) |
C7—C2—C3—C10 | 3.5 (4) | C22—C23—C24—C25 | 0.0 (5) |
C1—C2—C3—C10 | −177.1 (3) | C22—C23—C24—C19 | 179.9 (3) |
C2—C1—C5—C4 | −1.2 (4) | C20—C19—C24—C23 | −34.8 (5) |
C6—C1—C5—C4 | −179.1 (3) | C18—C19—C24—C23 | 145.5 (3) |
N3—C4—C5—C1 | 0.4 (4) | C20—C19—C24—C25 | 145.2 (3) |
C11—C4—C5—C1 | 178.1 (3) | C18—C19—C24—C25 | −34.5 (4) |
C5—C1—C6—O1 | 129.2 (3) | C23—C24—C25—C26 | 1.1 (5) |
C2—C1—C6—O1 | −48.7 (4) | C19—C24—C25—C26 | −178.9 (3) |
C5—C1—C6—O2 | −50.4 (4) | C24—C25—C26—N2 | −1.3 (5) |
C2—C1—C6—O2 | 131.7 (3) | C18—C17—N1—C21 | 0.5 (4) |
C1—C2—C7—C8 | 177.5 (3) | C18—C17—N1—Ag1 | 174.2 (2) |
C3—C2—C7—C8 | −3.2 (4) | C20—C21—N1—C17 | 0.1 (5) |
C2—C7—C8—C9 | 0.7 (5) | C20—C21—N1—Ag1 | −173.6 (2) |
C7—C8—C9—C10 | 1.5 (5) | C25—C26—N2—C22 | 0.3 (5) |
C8—C9—C10—C3 | −1.1 (5) | C25—C26—N2—Ag1i | −175.6 (2) |
N3—C3—C10—C9 | −179.6 (3) | C23—C22—N2—C26 | 0.9 (5) |
C2—C3—C10—C9 | −1.4 (5) | C23—C22—N2—Ag1i | 176.8 (2) |
N3—C4—C11—C12 | −155.1 (3) | C5—C4—N3—C3 | 1.0 (4) |
C5—C4—C11—C12 | 27.2 (4) | C11—C4—N3—C3 | −176.7 (2) |
N3—C4—C11—C16 | 27.2 (4) | C10—C3—N3—C4 | 176.4 (3) |
C5—C4—C11—C16 | −150.5 (3) | C2—C3—N3—C4 | −1.7 (4) |
C16—C11—C12—C13 | 0.0 (4) | O2—C6—O1—Ag1 | 58.6 (4) |
C4—C11—C12—C13 | −177.7 (3) | C1—C6—O1—Ag1 | −121.0 (2) |
C11—C12—C13—C14 | 0.1 (5) | C17—N1—Ag1—O1 | −39.8 (2) |
C12—C13—C14—C15 | −0.2 (5) | C21—N1—Ag1—O1 | 133.6 (2) |
C13—C14—C15—C16 | 0.2 (5) | C17—N1—Ag1—O1W | −122.7 (2) |
C14—C15—C16—C11 | 0.0 (5) | C21—N1—Ag1—O1W | 50.7 (2) |
C12—C11—C16—C15 | −0.1 (4) | C6—O1—Ag1—N1 | −134.9 (2) |
C4—C11—C16—C15 | 177.7 (3) | C6—O1—Ag1—N2ii | 50.3 (2) |
N1—C17—C18—C19 | −0.9 (5) | C6—O1—Ag1—O1W | −47.2 (2) |
Symmetry codes: (i) x−1, y, z−1; (ii) x+1, y, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O2 | 0.85 | 2.02 | 2.816 (3) | 156 |
O1W—H1B···O2iii | 0.85 | 1.97 | 2.805 (3) | 168 |
O2W—H2A···N3 | 0.84 | 2.12 | 2.944 (3) | 165 |
O2W—H2B···O3Wiv | 0.84 | 1.89 | 2.711 (3) | 167 |
O3W—H3A···O2Wv | 0.85 | 1.92 | 2.764 (3) | 172 |
O3W—H3B···O1 | 0.85 | 1.97 | 2.794 (3) | 162 |
Symmetry codes: (iii) −x+1, −y, −z+1; (iv) x+1, y, z; (v) x−1, −y+1/2, z−1/2. |
Experimental details
Crystal data |
Chemical formula | [Ag(C16H10NO2)(C10H8N2)(H2O)]·2H2O |
Mr | 566.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 151 |
a, b, c (Å) | 9.4006 (9), 27.461 (3), 9.5349 (9) |
β (°) | 105.987 (1) |
V (Å3) | 2366.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.90 |
Crystal size (mm) | 0.28 × 0.22 × 0.15 |
|
Data collection |
Diffractometer | Bruker APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.788, 0.877 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13019, 4645, 3708 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.099, 1.05 |
No. of reflections | 4645 |
No. of parameters | 316 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.98, −0.42 |
Selected geometric parameters (Å, º) topAg1—N1 | 2.156 (2) | Ag1—O1 | 2.598 (2) |
Ag1—N2i | 2.161 (3) | Ag1—O1W | 2.685 (2) |
| | | |
N1—Ag1—N2ii | 172.00 (9) | N1—Ag1—O1W | 88.57 (8) |
N1—Ag1—O1 | 96.64 (8) | N2ii—Ag1—O1W | 97.36 (9) |
N2ii—Ag1—O1 | 89.43 (8) | O1—Ag1—O1W | 83.08 (8) |
Symmetry codes: (i) x−1, y, z−1; (ii) x+1, y, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O2 | 0.85 | 2.02 | 2.816 (3) | 156 |
O1W—H1B···O2iii | 0.85 | 1.97 | 2.805 (3) | 168 |
O2W—H2A···N3 | 0.84 | 2.12 | 2.944 (3) | 165 |
O2W—H2B···O3Wiv | 0.84 | 1.89 | 2.711 (3) | 167 |
O3W—H3A···O2Wv | 0.85 | 1.92 | 2.764 (3) | 172 |
O3W—H3B···O1 | 0.85 | 1.97 | 2.794 (3) | 162 |
Symmetry codes: (iii) −x+1, −y, −z+1; (iv) x+1, y, z; (v) x−1, −y+1/2, z−1/2. |
In recent years, isonicotinic acid and its derivatives, bearing both neutral and anionic donor groups, have been widely used to construct metal–organic coordination polymers, not only from the viewpoint of structural interest (Xiong et al., 1999; Evans & Lin, 2000; Zheng et al., 2001; Lu & Babb, 2001), but also for targeting solid-state complexes with tailored properties such as nonlinear optical properties (Evans & Lin, 2002; Lin et al., 1998, 2000), inclusion behaviour (Aakeröy et al., 1999; Sekiya & Nishikiori, 2002; Sekiya et al., 2004; Zhang et al., 2001) and molecular magnetism (Chapman et al., 2001; Bu et al., 2005). However, as an analogue of isonicotinic acid, the use of 2-phenylquinoline-4-carboxylic acid (HL) to construct metal–organic frameworks has been less well investigated to date (Qin et al., 2002; Shen et al., 2007; Wang et al., 2010; Li et al., 2011; Zhang et al., 2009). The 2-phenylquinoline-4-carboxylate ligand, L, was selected based on the following considerations. It has larger conjugated π systems, and therefore π–π stacking and/or C—H···π interactions may play an important role in the formation of complexes, especially in the aspect of linking dinuclear or multinuclear discrete subunits or low-dimensional entities into higher-dimensional supramolecular frameworks. On the other hand, the coordination abilities of the quinoline N atoms may be weakened by adjacent larger groups, although the quinoline N atoms may still easily form hydrogen-bonding interactions with hydrogen-donor molecules. Besides, the introduction of an auxiliary ligand, such as 4,4'-bipyridyl-like linear bridging molecules, into the reaction system may generate interesting coordination architectures. In the present work, we report the synthesis and structure of the title silver(I) complex with 2-phenylquinoline-4-carboxylic acid, (I).
The crystal structure of (I) (Fig. 1) shows that the AgI centres are four-coordinated. Each AgI cation is coordinated by two N atoms of two different 4,4'-bipyridine (4,4'-bipy) ligands, one carboxylate O atom and one relatively weakly coordinated aqua ligand (Table 1 and Fig. 1). The AgI cations are bridged by 4,4'-bipy ligands to form a one-dimensional Ag–bipy chain running in the [101] direction (Fig. 2). Adjacent Ag–bipy chains are interconnected by hydrogen-bonding interactions to build up the two-dimensional crystal framework. The solvent water molecules are situated within the framework and stabilized by hydrogen-bonding interactions.
Seen from the [101] plane, there are four different orientations for L, two face-to-face and the other two back-to-back, and this arrangement is repeated thoughout the crystal structure (Fig. 3). Between two neighbouring back-to-back chains, coordinated water molecule O1W, as hydrogen-bond donor, interacts with noncoordinated carboxylate atom O2 in an intramolecular O1W—H1A···O2 hydrogen bond and an intermolecular O1W—H1B···O2i hydrogen bond (see Table 2 for geometric details and symmetry codes for all hydrogen bonds). Noncoordinated atoms O2 and O2i and two coordinated O1W water molecules in two adjacent polymeric chains are organized in an approximate quadrangle, with an O atom at each of the four corners. Between two neighbouring face-to-face polymeric chains, two solvent water molecules arrange themselves to form a hydrogen-bonded water dimer (O2W—H2B···O3Wii and O3W—H3A···O2Wiii), and this supramolecular water dimer is associated with the L ligand by hydrogen bonds through the coordinated O atom of the –COO- group and the N atom of L.
Hydrogen-bonding data indicate that solvent water molecule O2W, acting as a donor, is hydrogen-bonded to atom N3 of ligand L in another adjacent polymeric chain (O2W—H2A···N3 [Symmetry code?]) and to water molecule O3Wii (O2W—H2B···O3Wii), which in turn acts as a hydrogen-bond acceptor interacting with water molecule O3W. Solvent water molecule (O3W), also acting as a hydrogen-bond donor, is bonded to the monodentate carboxylate (–COOAg) group in a neighbouring chain (O3W—H3B···O1 [Symmetry code?]) and to water molecule O2Wiii (O3W—H3A···O2Wiii), which in turn acts as a hydrogen-bond acceptor interacting with water molecule O2W. Both O2W and O3W thus behave as both acceptors and donors, while L behaves solely as an acceptor. The water molecules are all three-coordinated, as usual.
Due to the introduction of 4,4'-bipy as a second ligand into the Ag–L system, complex (I) displays a distinctly different structure from [Ag(C16H10.5NO2)2] [chemical name?] (Zhang et al., 2009). Although as a potential coordinating group, unlike [Ag(C16H10.5NO2)2], the quinoline group does not coordinate to the AgI cation in (I), it shows hydrogen-bonding interactions with solvent water molecule O2W. The solvent water molecules, the coordinated water molecule and the one-dimensional chains are bridged through O—H···O and O—H···N hydrogen bonds to form a three-dimensional architecture.