Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105010498/fg1829sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270105010498/fg1829Isup2.hkl |
CCDC reference: 275494
Brown platelet crystals of (I) were obtained by slow evaporation of an 80% methanol solution ((v/v) of a mixture of 1,8-naphthyridine, salicylic acid and AgNO3 (molar ratio 4:4:1) at room temperature.
All H atoms were located from the difference Fourier maps, and were then regenerated in their ideal positions and treated as riding, with C—H = 0.93 and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C,O).
Data collection: RAPID-AUTO (Rigaku, 2003); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004) and CRYSTALS (Watkin et al., 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.
[Ag4(C7H5O3)4(C7H6O3)2(C8H6N2)4] | F(000) = 1776.0 |
Mr = 1776.75 | Dx = 1.728 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 21592 reflections |
a = 10.205 (12) Å | θ = 3.1–27.5° |
b = 13.129 (10) Å | µ = 1.21 mm−1 |
c = 25.82 (2) Å | T = 296 K |
β = 99.26 (4)° | Platelet, brown |
V = 3414 (5) Å3 | 0.3 × 0.3 × 0.03 mm |
Z = 2 |
Rigaku R-AXIS RAPID diffractometer | 7793 independent reflections |
Radiation source: fine-focus sealed tube | 4718 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −14→17 |
Tmin = 0.646, Tmax = 0.956 | l = −33→33 |
32278 measured reflections |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 0.80 | w = 1/[σ2(Fo2) + (0.0275P)2] where P = (Fo2 + 2Fc2)/3 |
7793 reflections | (Δ/σ)max < 0.001 |
474 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
[Ag4(C7H5O3)4(C7H6O3)2(C8H6N2)4] | V = 3414 (5) Å3 |
Mr = 1776.75 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.205 (12) Å | µ = 1.21 mm−1 |
b = 13.129 (10) Å | T = 296 K |
c = 25.82 (2) Å | 0.3 × 0.3 × 0.03 mm |
β = 99.26 (4)° |
Rigaku R-AXIS RAPID diffractometer | 7793 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4718 reflections with I > 2σ(I) |
Tmin = 0.646, Tmax = 0.956 | Rint = 0.033 |
32278 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 0.80 | Δρmax = 0.61 e Å−3 |
7793 reflections | Δρmin = −0.46 e Å−3 |
474 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.62246 (2) | 0.470444 (14) | 0.053221 (7) | 0.05080 (7) | |
Ag2 | 0.43514 (2) | 0.659495 (14) | 0.032040 (8) | 0.04803 (6) | |
O1 | 0.7000 (2) | 0.56194 (16) | 0.13328 (7) | 0.0796 (6) | |
O2 | 0.5667 (2) | 0.69507 (19) | 0.11643 (8) | 0.0926 (7) | |
O3 | 0.8993 (2) | 0.56971 (15) | 0.20552 (9) | 0.0809 (6) | |
H31 | 0.8466 | 0.5441 | 0.1818 | 0.097* | |
O4 | 0.34899 (19) | 0.83108 (12) | 0.05138 (7) | 0.0554 (5) | |
O5 | 0.15975 (19) | 0.83881 (14) | −0.00380 (7) | 0.0642 (5) | |
O6 | 0.3592 (2) | 0.88082 (16) | 0.14703 (7) | 0.0693 (6) | |
H61 | 0.3872 | 0.8600 | 0.1209 | 0.083* | |
O7 | 0.7892 (2) | 0.30060 (16) | 0.11288 (8) | 0.0735 (6) | |
O8 | 0.7143 (2) | 0.15175 (15) | 0.07836 (7) | 0.0716 (6) | |
H81 | 0.7541 | 0.1698 | 0.0548 | 0.086* | |
O9 | 0.7313 (3) | 0.34942 (17) | 0.20370 (9) | 0.0917 (7) | |
H91 | 0.7555 | 0.3587 | 0.1753 | 0.110* | |
N1 | 0.26915 (19) | 0.57922 (14) | 0.06134 (8) | 0.0422 (5) | |
N2 | 0.23070 (18) | 0.46334 (13) | −0.00694 (7) | 0.0401 (5) | |
N3 | 0.47323 (19) | 0.37828 (14) | 0.08676 (8) | 0.0422 (5) | |
N4 | 0.43871 (19) | 0.26271 (14) | 0.01825 (8) | 0.0445 (5) | |
C1 | 0.7541 (3) | 0.71093 (19) | 0.18246 (9) | 0.0454 (6) | |
C2 | 0.8666 (3) | 0.6677 (2) | 0.21153 (10) | 0.0513 (7) | |
C3 | 0.9501 (3) | 0.7268 (2) | 0.24770 (11) | 0.0672 (8) | |
H3 | 1.0258 | 0.6980 | 0.2671 | 0.081* | |
C4 | 0.9212 (3) | 0.8262 (2) | 0.25468 (12) | 0.0716 (9) | |
H4 | 0.9781 | 0.8654 | 0.2785 | 0.086* | |
C5 | 0.8101 (3) | 0.8692 (2) | 0.22723 (12) | 0.0670 (8) | |
H5 | 0.7908 | 0.9371 | 0.2328 | 0.080* | |
C6 | 0.7263 (3) | 0.8130 (2) | 0.19127 (10) | 0.0579 (7) | |
H6 | 0.6505 | 0.8430 | 0.1727 | 0.069* | |
C7 | 0.6651 (3) | 0.6526 (3) | 0.14125 (11) | 0.0600 (8) | |
C8 | 0.3107 (3) | 0.2684 (2) | 0.14376 (11) | 0.0656 (8) | |
H8 | 0.2559 | 0.2324 | 0.1627 | 0.079* | |
C9 | 0.3706 (3) | 0.3538 (3) | 0.16351 (11) | 0.0668 (8) | |
H9 | 0.3587 | 0.3773 | 0.1964 | 0.080* | |
C10 | 0.4513 (3) | 0.4073 (2) | 0.13394 (10) | 0.0545 (7) | |
H10 | 0.4920 | 0.4667 | 0.1481 | 0.065* | |
C11 | 0.2748 (3) | 0.1438 (2) | 0.07048 (13) | 0.0673 (9) | |
H11 | 0.2180 | 0.1046 | 0.0871 | 0.081* | |
C12 | 0.3032 (3) | 0.11495 (19) | 0.02341 (14) | 0.0680 (9) | |
H12 | 0.2683 | 0.0548 | 0.0079 | 0.082* | |
C13 | 0.3857 (3) | 0.17623 (18) | −0.00187 (12) | 0.0577 (7) | |
H13 | 0.4042 | 0.1554 | −0.0343 | 0.069* | |
C14 | 0.3309 (3) | 0.23303 (18) | 0.09425 (11) | 0.0515 (7) | |
C15 | 0.4141 (2) | 0.29125 (17) | 0.06626 (10) | 0.0415 (6) | |
C16 | 0.0724 (3) | 0.4918 (2) | 0.11084 (11) | 0.0615 (8) | |
H16 | 0.0069 | 0.4630 | 0.1274 | 0.074* | |
C17 | 0.1416 (3) | 0.5741 (2) | 0.13188 (11) | 0.0639 (8) | |
H17 | 0.1240 | 0.6027 | 0.1630 | 0.077* | |
C18 | 0.2395 (3) | 0.61519 (19) | 0.10616 (10) | 0.0545 (7) | |
H18 | 0.2868 | 0.6711 | 0.1213 | 0.065* | |
C19 | 0.0344 (3) | 0.36505 (19) | 0.03896 (11) | 0.0558 (7) | |
H19 | −0.0314 | 0.3324 | 0.0538 | 0.067* | |
C20 | 0.0679 (3) | 0.33116 (18) | −0.00674 (12) | 0.0569 (7) | |
H20 | 0.0261 | 0.2742 | −0.0233 | 0.068* | |
C21 | 0.1653 (3) | 0.38206 (18) | −0.02886 (10) | 0.0486 (6) | |
H21 | 0.1857 | 0.3582 | −0.0605 | 0.058* | |
C22 | 0.1006 (2) | 0.45027 (18) | 0.06360 (10) | 0.0465 (6) | |
C23 | 0.1996 (2) | 0.49776 (17) | 0.03935 (9) | 0.0391 (6) | |
C24 | 0.1614 (3) | 0.89646 (17) | 0.08262 (10) | 0.0432 (6) | |
C25 | 0.2317 (3) | 0.90972 (18) | 0.13364 (10) | 0.0516 (7) | |
C26 | 0.1699 (4) | 0.9551 (2) | 0.17221 (11) | 0.0707 (9) | |
H26 | 0.2161 | 0.9638 | 0.2060 | 0.085* | |
C27 | 0.0422 (4) | 0.9863 (2) | 0.16009 (14) | 0.0829 (11) | |
H27 | 0.0012 | 1.0158 | 0.1860 | 0.099* | |
C28 | −0.0291 (3) | 0.9753 (2) | 0.10992 (14) | 0.0813 (10) | |
H28 | −0.1165 | 0.9977 | 0.1022 | 0.098* | |
C29 | 0.0318 (3) | 0.93065 (19) | 0.07150 (11) | 0.0582 (7) | |
H29 | −0.0151 | 0.9235 | 0.0377 | 0.070* | |
C30 | 0.2289 (3) | 0.85233 (17) | 0.04077 (10) | 0.0441 (6) | |
C31 | 0.6695 (3) | 0.19006 (19) | 0.16174 (9) | 0.0482 (6) | |
C32 | 0.6767 (3) | 0.2571 (2) | 0.20436 (11) | 0.0565 (7) | |
C33 | 0.6194 (3) | 0.2307 (2) | 0.24801 (11) | 0.0688 (8) | |
H33 | 0.6252 | 0.2749 | 0.2764 | 0.083* | |
C34 | 0.5558 (3) | 0.1410 (3) | 0.24893 (12) | 0.0725 (9) | |
H34 | 0.5174 | 0.1241 | 0.2781 | 0.087* | |
C35 | 0.5464 (3) | 0.0738 (2) | 0.20731 (12) | 0.0691 (8) | |
H35 | 0.5018 | 0.0123 | 0.2085 | 0.083* | |
C36 | 0.6035 (3) | 0.0982 (2) | 0.16400 (11) | 0.0584 (7) | |
H36 | 0.5977 | 0.0527 | 0.1361 | 0.070* | |
C37 | 0.7311 (3) | 0.2187 (2) | 0.11563 (11) | 0.0563 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.05405 (14) | 0.05110 (12) | 0.04933 (12) | −0.01561 (10) | 0.01464 (10) | −0.00875 (10) |
Ag2 | 0.04922 (13) | 0.04452 (11) | 0.05226 (12) | −0.00788 (10) | 0.01394 (10) | −0.00773 (9) |
O1 | 0.1107 (19) | 0.0699 (14) | 0.0555 (13) | −0.0262 (13) | 0.0055 (12) | −0.0182 (11) |
O2 | 0.0747 (18) | 0.127 (2) | 0.0656 (14) | −0.0075 (15) | −0.0201 (13) | −0.0163 (13) |
O3 | 0.0860 (18) | 0.0647 (13) | 0.0894 (18) | 0.0110 (12) | 0.0063 (13) | −0.0077 (11) |
O4 | 0.0524 (13) | 0.0507 (11) | 0.0651 (12) | 0.0054 (9) | 0.0154 (10) | −0.0103 (9) |
O5 | 0.0612 (13) | 0.0835 (13) | 0.0491 (12) | −0.0083 (11) | 0.0122 (10) | −0.0104 (10) |
O6 | 0.0724 (16) | 0.0826 (14) | 0.0505 (12) | 0.0084 (11) | 0.0029 (11) | −0.0025 (10) |
O7 | 0.0735 (16) | 0.0772 (14) | 0.0741 (14) | −0.0083 (12) | 0.0247 (12) | 0.0046 (11) |
O8 | 0.0817 (16) | 0.0848 (14) | 0.0533 (12) | 0.0063 (12) | 0.0257 (11) | −0.0051 (11) |
O9 | 0.108 (2) | 0.0877 (16) | 0.0762 (16) | −0.0222 (14) | 0.0054 (15) | −0.0154 (13) |
N1 | 0.0418 (13) | 0.0392 (11) | 0.0459 (12) | 0.0030 (10) | 0.0075 (10) | 0.0020 (10) |
N2 | 0.0340 (12) | 0.0366 (10) | 0.0494 (12) | 0.0005 (9) | 0.0055 (10) | 0.0024 (10) |
N3 | 0.0378 (13) | 0.0445 (12) | 0.0445 (12) | 0.0045 (10) | 0.0072 (10) | 0.0038 (10) |
N4 | 0.0392 (13) | 0.0357 (11) | 0.0598 (14) | −0.0010 (9) | 0.0119 (11) | 0.0004 (10) |
C1 | 0.0419 (17) | 0.0600 (16) | 0.0350 (13) | −0.0118 (13) | 0.0085 (12) | −0.0045 (12) |
C2 | 0.0541 (19) | 0.0545 (17) | 0.0478 (16) | −0.0055 (14) | 0.0163 (14) | −0.0082 (13) |
C3 | 0.051 (2) | 0.087 (2) | 0.0591 (19) | −0.0062 (17) | −0.0055 (15) | −0.0047 (17) |
C4 | 0.064 (2) | 0.081 (2) | 0.068 (2) | −0.0252 (18) | 0.0069 (18) | −0.0286 (18) |
C5 | 0.072 (2) | 0.0567 (18) | 0.076 (2) | −0.0135 (16) | 0.0243 (19) | −0.0162 (16) |
C6 | 0.0555 (19) | 0.0618 (18) | 0.0582 (18) | −0.0028 (14) | 0.0146 (15) | −0.0032 (15) |
C7 | 0.062 (2) | 0.078 (2) | 0.0405 (16) | −0.0238 (18) | 0.0117 (15) | −0.0049 (16) |
C8 | 0.053 (2) | 0.083 (2) | 0.064 (2) | 0.0077 (17) | 0.0219 (16) | 0.0276 (17) |
C9 | 0.055 (2) | 0.096 (2) | 0.0521 (18) | 0.0069 (18) | 0.0163 (15) | 0.0077 (17) |
C10 | 0.0470 (18) | 0.0686 (18) | 0.0482 (16) | 0.0071 (14) | 0.0083 (14) | 0.0010 (14) |
C11 | 0.057 (2) | 0.0501 (17) | 0.098 (2) | −0.0041 (14) | 0.0196 (18) | 0.0212 (17) |
C12 | 0.059 (2) | 0.0358 (15) | 0.109 (3) | −0.0129 (13) | 0.0153 (19) | 0.0002 (16) |
C13 | 0.0491 (18) | 0.0444 (15) | 0.081 (2) | −0.0019 (13) | 0.0130 (15) | −0.0057 (14) |
C14 | 0.0403 (16) | 0.0462 (15) | 0.0687 (19) | 0.0048 (12) | 0.0115 (14) | 0.0174 (14) |
C15 | 0.0316 (15) | 0.0374 (13) | 0.0554 (16) | 0.0065 (11) | 0.0065 (12) | 0.0065 (12) |
C16 | 0.058 (2) | 0.0660 (19) | 0.0654 (19) | 0.0052 (16) | 0.0243 (16) | 0.0209 (16) |
C17 | 0.072 (2) | 0.074 (2) | 0.0514 (17) | 0.0085 (17) | 0.0255 (16) | 0.0055 (15) |
C18 | 0.065 (2) | 0.0496 (15) | 0.0511 (17) | 0.0021 (14) | 0.0143 (15) | 0.0023 (13) |
C19 | 0.0395 (17) | 0.0534 (17) | 0.074 (2) | −0.0015 (13) | 0.0089 (15) | 0.0206 (15) |
C20 | 0.0473 (18) | 0.0403 (14) | 0.080 (2) | −0.0084 (13) | 0.0012 (15) | 0.0084 (14) |
C21 | 0.0424 (17) | 0.0431 (14) | 0.0592 (17) | −0.0019 (12) | 0.0046 (13) | −0.0002 (12) |
C22 | 0.0405 (16) | 0.0442 (14) | 0.0560 (16) | 0.0058 (12) | 0.0110 (13) | 0.0131 (13) |
C23 | 0.0359 (15) | 0.0374 (13) | 0.0434 (14) | 0.0067 (11) | 0.0046 (12) | 0.0103 (11) |
C24 | 0.0491 (17) | 0.0363 (13) | 0.0465 (15) | −0.0002 (12) | 0.0149 (13) | 0.0060 (11) |
C25 | 0.064 (2) | 0.0431 (14) | 0.0510 (17) | 0.0034 (14) | 0.0184 (15) | 0.0075 (13) |
C26 | 0.100 (3) | 0.0672 (19) | 0.0497 (17) | 0.0058 (18) | 0.0275 (18) | 0.0000 (15) |
C27 | 0.108 (3) | 0.079 (2) | 0.073 (2) | 0.017 (2) | 0.052 (2) | 0.0004 (19) |
C28 | 0.069 (2) | 0.088 (2) | 0.096 (3) | 0.0234 (19) | 0.038 (2) | 0.013 (2) |
C29 | 0.055 (2) | 0.0591 (17) | 0.0632 (18) | 0.0045 (14) | 0.0189 (15) | 0.0042 (14) |
C30 | 0.0496 (18) | 0.0354 (13) | 0.0488 (16) | −0.0065 (12) | 0.0131 (14) | 0.0016 (12) |
C31 | 0.0452 (17) | 0.0583 (16) | 0.0410 (15) | 0.0136 (13) | 0.0060 (12) | 0.0019 (13) |
C32 | 0.0560 (19) | 0.0549 (17) | 0.0552 (18) | −0.0009 (14) | −0.0010 (14) | −0.0041 (14) |
C33 | 0.086 (2) | 0.080 (2) | 0.0403 (16) | 0.0068 (19) | 0.0088 (16) | −0.0065 (15) |
C34 | 0.079 (2) | 0.087 (2) | 0.0551 (19) | 0.0105 (19) | 0.0223 (17) | 0.0153 (18) |
C35 | 0.073 (2) | 0.0648 (19) | 0.071 (2) | 0.0010 (16) | 0.0175 (18) | 0.0076 (17) |
C36 | 0.062 (2) | 0.0558 (17) | 0.0570 (18) | 0.0066 (15) | 0.0083 (15) | −0.0019 (14) |
C37 | 0.0488 (19) | 0.0652 (18) | 0.0545 (18) | 0.0169 (15) | 0.0068 (14) | 0.0028 (16) |
Ag1—N3 | 2.227 (2) | C8—H8 | 0.93 |
Ag1—N2i | 2.237 (2) | C9—C10 | 1.399 (4) |
Ag1—O1 | 2.412 (2) | C9—H9 | 0.93 |
Ag1—Ag2i | 2.772 (2) | C10—H10 | 0.93 |
Ag1—Ag2 | 3.127 (2) | C11—C12 | 1.349 (4) |
Ag2—N4i | 2.219 (2) | C11—C14 | 1.402 (4) |
Ag2—N1 | 2.228 (3) | C11—H11 | 0.93 |
Ag2—O2 | 2.414 (3) | C12—C13 | 1.399 (4) |
Ag2—O4 | 2.498 (2) | C12—H12 | 0.93 |
Ag2—Ag1i | 2.7725 (16) | C13—H13 | 0.93 |
O1—C7 | 1.269 (4) | C14—C15 | 1.422 (3) |
O2—C7 | 1.234 (4) | C16—C17 | 1.356 (4) |
O3—C2 | 1.345 (3) | C16—C22 | 1.407 (4) |
O3—H31 | 0.82 | C16—H16 | 0.93 |
O4—C30 | 1.244 (3) | C17—C18 | 1.394 (4) |
O5—C30 | 1.262 (3) | C17—H17 | 0.93 |
O6—C25 | 1.346 (3) | C18—H18 | 0.93 |
O6—H61 | 0.82 | C19—C20 | 1.355 (4) |
O7—C37 | 1.235 (3) | C19—C22 | 1.405 (4) |
O8—C37 | 1.295 (3) | C19—H19 | 0.93 |
O8—H81 | 0.82 | C20—C21 | 1.394 (3) |
O9—C32 | 1.335 (3) | C20—H20 | 0.93 |
O9—H91 | 0.82 | C21—H21 | 0.93 |
N1—C18 | 1.329 (3) | C22—C23 | 1.416 (3) |
N1—C23 | 1.357 (3) | C24—C29 | 1.382 (4) |
N2—C21 | 1.335 (3) | C24—C25 | 1.406 (4) |
N2—C23 | 1.362 (3) | C24—C30 | 1.489 (3) |
N2—Ag1i | 2.237 (2) | C25—C26 | 1.395 (4) |
N3—C10 | 1.329 (3) | C26—C27 | 1.354 (4) |
N3—C15 | 1.359 (3) | C26—H26 | 0.93 |
N4—C13 | 1.327 (3) | C27—C28 | 1.388 (5) |
N4—C15 | 1.357 (3) | C27—H27 | 0.93 |
N4—Ag2i | 2.219 (2) | C28—C29 | 1.383 (4) |
C1—C2 | 1.388 (4) | C28—H28 | 0.93 |
C1—C6 | 1.396 (3) | C29—H29 | 0.93 |
C1—C7 | 1.494 (4) | C31—C36 | 1.387 (4) |
C2—C3 | 1.394 (4) | C31—C32 | 1.402 (3) |
C3—C4 | 1.356 (4) | C31—C37 | 1.482 (4) |
C3—H3 | 0.93 | C32—C33 | 1.394 (4) |
C4—C5 | 1.359 (4) | C33—C34 | 1.346 (4) |
C4—H4 | 0.93 | C33—H33 | 0.93 |
C5—C6 | 1.373 (4) | C34—C35 | 1.382 (4) |
C5—H5 | 0.93 | C34—H34 | 0.93 |
C6—H6 | 0.93 | C35—C36 | 1.379 (4) |
C8—C9 | 1.339 (4) | C35—H35 | 0.93 |
C8—C14 | 1.406 (4) | C36—H36 | 0.93 |
N3—Ag1—N2i | 167.87 (7) | C11—C12—H12 | 120.3 |
N3—Ag1—O1 | 95.04 (9) | C13—C12—H12 | 120.3 |
N2i—Ag1—O1 | 96.25 (9) | N4—C13—C12 | 123.2 (3) |
N3—Ag1—Ag2i | 84.47 (7) | N4—C13—H13 | 118.4 |
N2i—Ag1—Ag2i | 83.66 (7) | C12—C13—H13 | 118.4 |
O1—Ag1—Ag2i | 170.27 (6) | C11—C14—C8 | 124.4 (3) |
N3—Ag1—Ag2 | 93.57 (8) | C11—C14—C15 | 117.5 (3) |
N2i—Ag1—Ag2 | 92.36 (8) | C8—C14—C15 | 118.1 (3) |
O1—Ag1—Ag2 | 82.04 (7) | N4—C15—N3 | 116.9 (2) |
Ag2i—Ag1—Ag2 | 107.69 (5) | N4—C15—C14 | 122.0 (2) |
N4i—Ag2—N1 | 163.87 (8) | N3—C15—C14 | 121.2 (2) |
N4i—Ag2—O2 | 98.53 (10) | C17—C16—C22 | 119.3 (2) |
N1—Ag2—O2 | 97.34 (10) | C17—C16—H16 | 120.3 |
N4i—Ag2—O4 | 87.58 (8) | C22—C16—H16 | 120.3 |
N1—Ag2—O4 | 92.72 (8) | C16—C17—C18 | 119.0 (3) |
O2—Ag2—O4 | 78.90 (8) | C16—C17—H17 | 120.5 |
N4i—Ag2—Ag1i | 83.53 (7) | C18—C17—H17 | 120.5 |
N1—Ag2—Ag1i | 84.43 (7) | N1—C18—C17 | 123.9 (3) |
O2—Ag2—Ag1i | 148.42 (7) | N1—C18—H18 | 118.0 |
O4—Ag2—Ag1i | 132.63 (5) | C17—C18—H18 | 118.0 |
N4i—Ag2—Ag1 | 94.12 (8) | C20—C19—C22 | 119.0 (2) |
N1—Ag2—Ag1 | 92.40 (8) | C20—C19—H19 | 120.5 |
O2—Ag2—Ag1 | 76.12 (7) | C22—C19—H19 | 120.5 |
O4—Ag2—Ag1 | 154.95 (5) | C19—C20—C21 | 119.7 (3) |
Ag1i—Ag2—Ag1 | 72.30 (5) | C19—C20—H20 | 120.1 |
C7—O1—Ag1 | 123.0 (2) | C21—C20—H20 | 120.1 |
C7—O2—Ag2 | 132.0 (2) | N2—C21—C20 | 123.4 (2) |
C2—O3—H31 | 109.5 | N2—C21—H21 | 118.3 |
C30—O4—Ag2 | 121.62 (16) | C20—C21—H21 | 118.3 |
C25—O6—H61 | 109.5 | C19—C22—C16 | 123.4 (2) |
C37—O8—H81 | 109.5 | C19—C22—C23 | 118.4 (2) |
C32—O9—H91 | 109.5 | C16—C22—C23 | 118.2 (2) |
C18—N1—C23 | 117.9 (2) | N1—C23—N2 | 116.7 (2) |
C18—N1—Ag2 | 114.82 (17) | N1—C23—C22 | 121.6 (2) |
C23—N1—Ag2 | 127.29 (15) | N2—C23—C22 | 121.7 (2) |
C21—N2—C23 | 117.8 (2) | C29—C24—C25 | 118.8 (2) |
C21—N2—Ag1i | 114.60 (16) | C29—C24—C30 | 121.0 (3) |
C23—N2—Ag1i | 127.61 (15) | C25—C24—C30 | 120.1 (2) |
C10—N3—C15 | 117.9 (2) | O6—C25—C26 | 117.8 (3) |
C10—N3—Ag1 | 115.26 (17) | O6—C25—C24 | 122.2 (2) |
C15—N3—Ag1 | 126.45 (15) | C26—C25—C24 | 120.0 (3) |
C13—N4—C15 | 118.0 (2) | C27—C26—C25 | 119.6 (3) |
C13—N4—Ag2i | 113.78 (17) | C27—C26—H26 | 120.2 |
C15—N4—Ag2i | 128.16 (16) | C25—C26—H26 | 120.2 |
C2—C1—C6 | 118.4 (2) | C26—C27—C28 | 121.7 (3) |
C2—C1—C7 | 122.1 (3) | C26—C27—H27 | 119.2 |
C6—C1—C7 | 119.4 (3) | C28—C27—H27 | 119.2 |
O3—C2—C1 | 121.8 (2) | C29—C28—C27 | 119.0 (3) |
O3—C2—C3 | 118.3 (3) | C29—C28—H28 | 120.5 |
C1—C2—C3 | 119.9 (3) | C27—C28—H28 | 120.5 |
C4—C3—C2 | 120.1 (3) | C24—C29—C28 | 120.9 (3) |
C4—C3—H3 | 119.9 | C24—C29—H29 | 119.5 |
C2—C3—H3 | 119.9 | C28—C29—H29 | 119.5 |
C3—C4—C5 | 120.7 (3) | O4—C30—O5 | 123.8 (2) |
C3—C4—H4 | 119.6 | O4—C30—C24 | 118.8 (2) |
C5—C4—H4 | 119.6 | O5—C30—C24 | 117.4 (3) |
C4—C5—C6 | 120.4 (3) | C36—C31—C32 | 118.5 (2) |
C4—C5—H5 | 119.8 | C36—C31—C37 | 121.8 (2) |
C6—C5—H5 | 119.8 | C32—C31—C37 | 119.7 (3) |
C5—C6—C1 | 120.4 (3) | O9—C32—C33 | 117.8 (3) |
C5—C6—H6 | 119.8 | O9—C32—C31 | 121.9 (3) |
C1—C6—H6 | 119.8 | C33—C32—C31 | 120.2 (3) |
O2—C7—O1 | 124.4 (3) | C34—C33—C32 | 119.9 (3) |
O2—C7—C1 | 119.3 (3) | C34—C33—H33 | 120.1 |
O1—C7—C1 | 116.3 (3) | C32—C33—H33 | 120.1 |
C9—C8—C14 | 119.9 (3) | C33—C34—C35 | 121.2 (3) |
C9—C8—H8 | 120.1 | C33—C34—H34 | 119.4 |
C14—C8—H8 | 120.1 | C35—C34—H34 | 119.4 |
C8—C9—C10 | 119.1 (3) | C36—C35—C34 | 119.8 (3) |
C8—C9—H9 | 120.5 | C36—C35—H35 | 120.1 |
C10—C9—H9 | 120.5 | C34—C35—H35 | 120.1 |
N3—C10—C9 | 123.8 (3) | C35—C36—C31 | 120.5 (3) |
N3—C10—H10 | 118.1 | C35—C36—H36 | 119.8 |
C9—C10—H10 | 118.1 | C31—C36—H36 | 119.8 |
C12—C11—C14 | 119.8 (3) | O7—C37—O8 | 123.8 (3) |
C12—C11—H11 | 120.1 | O7—C37—C31 | 122.5 (3) |
C14—C11—H11 | 120.1 | O8—C37—C31 | 113.7 (3) |
C11—C12—C13 | 119.5 (3) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H31···O1 | 0.82 | 1.81 | 2.531 (4) | 147 |
O6—H61···O4 | 0.82 | 1.81 | 2.540 (4) | 147 |
O8—H81···O5i | 0.82 | 1.70 | 2.484 (4) | 159 |
O9—H91···O7 | 0.82 | 1.86 | 2.589 (4) | 147 |
C16—H16···O3ii | 0.93 | 2.82 | 3.396 (5) | 121 |
C27—H27···O3iii | 0.93 | 2.91 | 3.596 (6) | 132 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag4(C7H5O3)4(C7H6O3)2(C8H6N2)4] |
Mr | 1776.75 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 10.205 (12), 13.129 (10), 25.82 (2) |
β (°) | 99.26 (4) |
V (Å3) | 3414 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.21 |
Crystal size (mm) | 0.3 × 0.3 × 0.03 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.646, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 32278, 7793, 4718 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.054, 0.80 |
No. of reflections | 7793 |
No. of parameters | 474 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.61, −0.46 |
Computer programs: RAPID-AUTO (Rigaku, 2003), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2004) and CRYSTALS (Watkin et al., 1996), SIR97 (Altomare et al., 1999) and DIRDIF99 (Beurskens et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPIII (Farrugia, 1997) and PLATON (Spek, 2003), CrystalStructure.
Ag1—N3 | 2.227 (2) | Ag2—N4i | 2.219 (2) |
Ag1—N2i | 2.237 (2) | Ag2—N1 | 2.228 (3) |
Ag1—O1 | 2.412 (2) | Ag2—O2 | 2.414 (3) |
Ag1—Ag2i | 2.772 (2) | Ag2—O4 | 2.498 (2) |
Ag1—Ag2 | 3.127 (2) | Ag2—Ag1i | 2.7725 (16) |
N3—Ag1—N2i | 167.87 (7) | N4i—Ag2—O4 | 87.58 (8) |
N3—Ag1—O1 | 95.04 (9) | N1—Ag2—O4 | 92.72 (8) |
N2i—Ag1—O1 | 96.25 (9) | O2—Ag2—O4 | 78.90 (8) |
N3—Ag1—Ag2i | 84.47 (7) | N4i—Ag2—Ag1i | 83.53 (7) |
N2i—Ag1—Ag2i | 83.66 (7) | N1—Ag2—Ag1i | 84.43 (7) |
O1—Ag1—Ag2i | 170.27 (6) | O2—Ag2—Ag1i | 148.42 (7) |
N3—Ag1—Ag2 | 93.57 (8) | O4—Ag2—Ag1i | 132.63 (5) |
N2i—Ag1—Ag2 | 92.36 (8) | N4i—Ag2—Ag1 | 94.12 (8) |
O1—Ag1—Ag2 | 82.04 (7) | N1—Ag2—Ag1 | 92.40 (8) |
Ag2i—Ag1—Ag2 | 107.69 (5) | O2—Ag2—Ag1 | 76.12 (7) |
N4i—Ag2—N1 | 163.87 (8) | O4—Ag2—Ag1 | 154.95 (5) |
N4i—Ag2—O2 | 98.53 (10) | Ag1i—Ag2—Ag1 | 72.30 (5) |
N1—Ag2—O2 | 97.34 (10) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H31···O1 | 0.82 | 1.81 | 2.531 (4) | 147 |
O6—H61···O4 | 0.82 | 1.81 | 2.540 (4) | 147 |
O8—H81···O5i | 0.82 | 1.70 | 2.484 (4) | 159 |
O9—H91···O7 | 0.82 | 1.86 | 2.589 (4) | 147 |
C16—H16···O3ii | 0.93 | 2.82 | 3.396 (5) | 121 |
C27—H27···O3iii | 0.93 | 2.91 | 3.596 (6) | 132 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1/2. |
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The two active N,N' donor atoms in 1,8-naphthyridine (napy) can act in different coordination modes, such as monodentate (Dewer et al., 1975; Enwall & Emerson, 1979), bidentate (Bodner & Hendricker, 1973; Epstein et al., 1974; Munakata et al., 1990). In the case of Ag(napy-N) type complexes, napy always acts as a bridging ligand to form planar binuclear complexes (Tsuda et al., 1989; Griffith et al., 1995; Koizumi & Tanaka, 2004). It is also known that silver complexes with salicylic acid (SA) are also based on bis(carboxylato-O,O')-bridged disilver nucleus (Movsumov et al., 1990).
In this present study, we designed a mixed-ligand silver complex using napy and SA ligands and synthesized the unique title tetrasilver complex, (I). Complex (I) is the first example in which there are two kinds of Ag—Ag bridges, i.e. O,O' and N,N' bridges, coexisting in one complex molecule.
The structure of complex (I) is shown in Fig. 1, with principal dimensions given in Table 1. Four AgI atoms lie about an inversion centre and as a consequence are perfectly planar. Atom Ag1 has a distorted octahedral coordination, being bonded to two N atoms [N3 and N2(1 − x,1 − y,-z)] from two napy ligands, one carboxylate O1 atom from a bidentate salicylate ligand, two adjacent Ag2 atoms, and (weakly) to carboxyl atom O7 of a salicylic acid molecule. Atom Ag2 also has a distorted octahedral coordination geometry, in which Ag1(1 − x,1 − y,-z), N1, N4(1 − x,1 − y,-z) and the salicylate O2 atoms form the equatorial plane, and Ag1 and salicylate O4 atoms complete the octahedron. As can be seen in Fig. 1, all salicylic hydroxy groups participate in intramolecular O—H···O hydrogen bonds (Table 2).
Each napy molecule acts as a bidentate ligand and pairs form a rigid bis(napy-N,N')-bridged disilver unit. In this unit, the eight-membered bis-chelate ring (–Ag—N—C—N—Ag—N—C—N–) is almost planar but is slightly folded [6.97 (10)°] about the Ag—Ag axis. Two inversion-related salicylate moieties act as bidentate bridging ligands to form a ten-membered chelate ring (–Ag—Ag—O—C—O—Ag—Ag—O—C—O–). As shown in Fig. 2, the two bridging salicylate aromatic rings are tilted away from the ten-membered chelate ring plane by 18.86 (10)°. The eight-membered chelate rings and the ten-membered chelate rings are essentially orthogonal.
In (I), both the average distances of Ag—O [bridged O; 2.413 (2) Å] and Ag—N [2.228 (6) Å] are longer than the corresponding values in complexes with only one kind of bridge unit within an O,O' or N,N' bridge, e.g. 2.180 (4) and 2.196 (5) Å for the Ag—O distance in an O,O'-bridged silver–salicylate complex (Movsumov et al., 1990) and 2.187 (3)–2.213 (4) Å for the Ag—N distances in N,N'-bridged napy complexes (Tsuda et al., 1989; Munakata et al., 1990; Griffith et al., 1995; Koizumi & Tanaka, 2004). This suggests that the coordination interaction of Ag with the ligand atoms, O and N, in the mixed-bridged complex, (I), may be weakened.
There are two types of Ag—Ag interaction in (I). One is a weaker Ag1—Ag2 interaction [3.127 (2) Å] formed by the carboxylato O,O' bridge. The other is a relatively stronger Ag1—Ag2(1 − x,1 − y,-z) interaction [2.773 (2) Å] formed by the napy N,N' bridge. Comparing with analogous complexes, the carboxylate-bridged value is much larger than the values in the literature, such as 2.855 (1) Å in disilver(I) disalicylate (Movsumov et al., 1990), 2.953 (1) Å in catena-bis(4-aminobenzoato)disilver(I) (Kristiansson, 2001) and 2.761 (2) Å in diaquabis(4-hydroxybenzenecarboxylato)disilver(I) tetrahydrate (Wang & Okabe, 2005). On the other hand, the napy-bridged Ag—Ag separation is almost within the reported ranges, from 2.748 (2) Å in [Ag2(µ-napy)2](ClO4)2 (Tsuda et al., 1989) to 2.779 (1) Å in [Ag2(µ-napy)2](PF6)2 (Koizumi & Tanaka, 2004) to 2.780 (1) Å in [Ag2(µ-napy)2](NO3)2 (Griffith et al., 1995).
The pairs of the two napy rings are oriented almost parallel and overlap to form π–π stacking, with ring-centroid-to-ring-centroid distances of 3.376 (4) and 3.343 (4) Å for rings N1/C16–C18/C22/C23 and N3/C8–C10/C14/C15, and rings N2/C19–C23 and N4/C11–C15. Intermolecular stacking between the napy rings is also present. Ring N2/C19–C23 overlaps with the inversion related ring at (−x, 1 − y, −z), with an interplanar distance of 3.368 (2) Å and a centroid···centroid separation of 3.514 Å. There are also C—H···O interactions (Table 2) between translation-related and screw-axis-related complexes, which link them along the a and b directions