Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059764/gw2032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059764/gw2032Isup2.hkl |
CCDC reference: 672725
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.091
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor OW2 - H2B ... ?
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ag1 - N4 .. 5.50 su PLAT420_ALERT_2_C D-H Without Acceptor N1 - H2N ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 11
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For studies on silver sulfonates, see Liu et al. (2007) and Li et al. (2006).
For related literature, see: Aakeröy & Beatty (1998); Cote & Shimizu (2004); Shimizu et al. (1998); Smith et al. (1996).
An aqueous solution (10 ml) of p-aminobenzenesulfonic acid (0.5 mmol) was added to solid Ag2CO3 (0.25 mmol) and stirred for several minutes until no further CO2 was given off. The 1-(3-(1H-imidazol-1-yl)methyl)benzyl)-1H-imidazole (0.5 mmol) was then added and a precipitate was formed. The precipitate was dissolved by ammonium hydroxide. Crystals of (I) were obtained by evaporation of the solution for several days at room temperature.
H atoms bonded to N atom were located in a difference map and refined with distance restraints of N—H = 0.85±0.01 Å. H atoms bonded to C atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier). H atoms bonded to O atoms of water molecules were located in a difference Fourier map and refined isotropically with distance restraints of O—H = 0.85±0.01 Å and H···H = 1.3±0.01 Å, with Uiso(H) = 1.5 Ueq(N).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) -x + 1, -y + 2, -z + 1. |
[Ag2(C14H14N4)2](C6H6NO3S)2·6H2O | F(000) = 2336 |
Mr = 1144.78 | Dx = 1.666 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5221 reflections |
a = 14.842 (3) Å | θ = 3.1–27.5° |
b = 16.283 (3) Å | µ = 1.02 mm−1 |
c = 19.527 (4) Å | T = 293 K |
β = 104.76 (3)° | Block, colorless |
V = 4563.6 (16) Å3 | 0.27 × 0.26 × 0.19 mm |
Z = 4 |
Rigaku RAXIS-RAPID diffractometer | 5221 independent reflections |
Radiation source: fine-focus sealed tube | 4333 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −19→15 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −20→21 |
Tmin = 0.698, Tmax = 0.811 | l = −25→25 |
22007 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0469P)2 + 5.1924P] where P = (Fo2 + 2Fc2)/3 |
5221 reflections | (Δ/σ)max = 0.004 |
324 parameters | Δρmax = 0.91 e Å−3 |
11 restraints | Δρmin = −0.49 e Å−3 |
[Ag2(C14H14N4)2](C6H6NO3S)2·6H2O | V = 4563.6 (16) Å3 |
Mr = 1144.78 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 14.842 (3) Å | µ = 1.02 mm−1 |
b = 16.283 (3) Å | T = 293 K |
c = 19.527 (4) Å | 0.27 × 0.26 × 0.19 mm |
β = 104.76 (3)° |
Rigaku RAXIS-RAPID diffractometer | 5221 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4333 reflections with I > 2σ(I) |
Tmin = 0.698, Tmax = 0.811 | Rint = 0.033 |
22007 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 11 restraints |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.91 e Å−3 |
5221 reflections | Δρmin = −0.49 e Å−3 |
324 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 | 0.449998 (13) | 1.092109 (13) | 0.518907 (12) | 0.04061 (9) | |
C1 | 0.18894 (16) | 0.84749 (15) | 0.31821 (13) | 0.0290 (5) | |
H1AA | 0.1922 | 0.7939 | 0.2973 | 0.035* | |
H2AA | 0.1956 | 0.8887 | 0.2840 | 0.035* | |
C2 | 0.73559 (17) | 1.15989 (15) | 0.54897 (13) | 0.0319 (5) | |
H2 | 0.7865 | 1.1780 | 0.5335 | 0.038* | |
C3 | 0.09499 (15) | 0.85728 (14) | 0.33396 (12) | 0.0256 (5) | |
C4 | 0.26422 (17) | 1.05237 (15) | 0.41358 (14) | 0.0321 (5) | |
H4 | 0.2926 | 1.0561 | 0.3764 | 0.039* | |
C5 | −0.03160 (17) | 0.93772 (16) | 0.35446 (13) | 0.0329 (5) | |
H5 | −0.0578 | 0.9886 | 0.3593 | 0.040* | |
C6 | 0.05636 (15) | 0.93418 (14) | 0.34222 (12) | 0.0257 (5) | |
C7 | 0.16588 (19) | 0.85770 (15) | 0.66231 (14) | 0.0347 (6) | |
C8 | 0.0204 (2) | 0.78904 (17) | 0.65491 (16) | 0.0422 (6) | |
H8 | −0.0197 | 0.7628 | 0.6775 | 0.051* | |
C9 | −0.0061 (2) | 0.79756 (15) | 0.58140 (16) | 0.0387 (6) | |
C10 | 0.10692 (17) | 1.01380 (14) | 0.33853 (13) | 0.0312 (5) | |
H10A | 0.1393 | 1.0100 | 0.3013 | 0.037* | |
H10B | 0.0618 | 1.0580 | 0.3264 | 0.037* | |
C11 | 0.15902 (17) | 1.03440 (16) | 0.47255 (14) | 0.0343 (5) | |
H11 | 0.1030 | 1.0236 | 0.4840 | 0.041* | |
C12 | −0.08107 (17) | 0.86696 (18) | 0.35968 (14) | 0.0362 (6) | |
H12 | −0.1400 | 0.8703 | 0.3679 | 0.043* | |
C13 | 0.64699 (16) | 1.12020 (16) | 0.61609 (14) | 0.0310 (5) | |
H13 | 0.6271 | 1.1062 | 0.6560 | 0.037* | |
C14 | 0.04452 (17) | 0.78665 (15) | 0.33941 (14) | 0.0324 (5) | |
H14 | 0.0698 | 0.7355 | 0.3341 | 0.039* | |
C15 | 0.1045 (2) | 0.81852 (16) | 0.69489 (15) | 0.0402 (6) | |
H15 | 0.1202 | 0.8122 | 0.7438 | 0.048* | |
C16 | −0.04243 (18) | 0.79123 (17) | 0.35252 (14) | 0.0372 (6) | |
H16 | −0.0750 | 0.7434 | 0.3565 | 0.045* | |
C17 | 0.0561 (2) | 0.83721 (17) | 0.54977 (15) | 0.0422 (6) | |
H17 | 0.0405 | 0.8438 | 0.5009 | 0.051* | |
C18 | 0.24085 (17) | 1.05413 (17) | 0.51802 (14) | 0.0358 (6) | |
H18 | 0.2508 | 1.0594 | 0.5668 | 0.043* | |
C19 | 0.1406 (2) | 0.86694 (17) | 0.58966 (15) | 0.0389 (6) | |
H19 | 0.1807 | 0.8934 | 0.5673 | 0.047* | |
C20 | 0.64898 (17) | 1.14382 (16) | 0.50806 (14) | 0.0344 (5) | |
H20 | 0.6303 | 1.1489 | 0.4590 | 0.041* | |
N1 | −0.0886 (2) | 0.76439 (16) | 0.54189 (17) | 0.0481 (6) | |
H1N | −0.132 (2) | 0.760 (3) | 0.563 (2) | 0.084 (15)* | |
H2N | −0.109 (3) | 0.783 (3) | 0.4999 (10) | 0.080 (14)* | |
N2 | 0.17443 (13) | 1.03327 (11) | 0.40591 (11) | 0.0268 (4) | |
N3 | 0.73354 (13) | 1.14420 (11) | 0.61745 (10) | 0.0244 (4) | |
N4 | 0.30739 (14) | 1.06528 (13) | 0.48088 (12) | 0.0339 (5) | |
N5 | 0.59315 (14) | 1.11888 (13) | 0.55039 (12) | 0.0313 (4) | |
O1 | 0.29951 (17) | 0.85170 (14) | 0.77672 (12) | 0.0566 (6) | |
O2 | 0.25394 (14) | 0.98490 (12) | 0.72646 (12) | 0.0474 (5) | |
O3 | 0.33681 (15) | 0.89252 (13) | 0.66753 (12) | 0.0497 (5) | |
S1 | 0.27191 (5) | 0.89939 (4) | 0.71192 (4) | 0.03645 (15) | |
OW1 | 0.2289 (2) | 0.74243 (17) | 0.87271 (17) | 0.0708 (7) | |
H1B | 0.243 (4) | 0.774 (3) | 0.842 (2) | 0.106* | |
H1A | 0.202 (3) | 0.701 (2) | 0.850 (3) | 0.106* | |
OW2 | 0.3692 (4) | 1.10983 (19) | 0.7022 (2) | 0.1041 (13) | |
H2A | 0.331 (3) | 1.072 (3) | 0.703 (4) | 0.156* | |
H2B | 0.421 (2) | 1.085 (3) | 0.712 (4) | 0.156* | |
OW3 | 0.5016 (4) | 0.9682 (4) | 0.6533 (2) | 0.167 (3) | |
H3A | 0.445 (2) | 0.983 (5) | 0.638 (4) | 0.250* | |
H3B | 0.496 (7) | 0.929 (4) | 0.680 (4) | 0.250* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.02279 (11) | 0.04981 (14) | 0.04500 (14) | −0.00688 (7) | 0.00086 (8) | −0.00582 (9) |
C1 | 0.0220 (11) | 0.0381 (12) | 0.0248 (12) | 0.0044 (8) | 0.0022 (9) | −0.0043 (9) |
C2 | 0.0251 (12) | 0.0412 (13) | 0.0291 (12) | −0.0012 (9) | 0.0062 (10) | 0.0036 (10) |
C3 | 0.0201 (11) | 0.0311 (11) | 0.0220 (11) | 0.0015 (8) | −0.0010 (8) | −0.0034 (9) |
C4 | 0.0282 (12) | 0.0318 (12) | 0.0370 (14) | −0.0042 (9) | 0.0094 (10) | −0.0011 (10) |
C5 | 0.0251 (12) | 0.0416 (13) | 0.0283 (12) | 0.0083 (9) | −0.0002 (9) | −0.0088 (10) |
C6 | 0.0213 (11) | 0.0304 (11) | 0.0214 (11) | 0.0017 (8) | −0.0019 (8) | −0.0040 (9) |
C7 | 0.0453 (15) | 0.0265 (11) | 0.0358 (14) | 0.0102 (10) | 0.0165 (12) | 0.0000 (10) |
C8 | 0.0500 (17) | 0.0365 (14) | 0.0460 (16) | −0.0001 (11) | 0.0227 (14) | 0.0025 (12) |
C9 | 0.0464 (16) | 0.0290 (12) | 0.0427 (15) | 0.0064 (10) | 0.0151 (12) | −0.0049 (11) |
C10 | 0.0315 (12) | 0.0298 (11) | 0.0276 (12) | 0.0018 (9) | −0.0010 (10) | 0.0011 (9) |
C11 | 0.0272 (12) | 0.0429 (13) | 0.0336 (13) | 0.0003 (10) | 0.0092 (10) | −0.0071 (11) |
C12 | 0.0199 (11) | 0.0568 (16) | 0.0309 (13) | −0.0026 (10) | 0.0048 (10) | −0.0062 (12) |
C13 | 0.0232 (11) | 0.0395 (12) | 0.0310 (12) | −0.0010 (9) | 0.0080 (10) | −0.0025 (10) |
C14 | 0.0289 (12) | 0.0311 (12) | 0.0335 (13) | −0.0007 (9) | 0.0014 (10) | −0.0070 (10) |
C15 | 0.0535 (17) | 0.0386 (14) | 0.0329 (14) | 0.0074 (11) | 0.0192 (12) | 0.0033 (11) |
C16 | 0.0279 (13) | 0.0459 (14) | 0.0341 (14) | −0.0114 (10) | 0.0010 (10) | −0.0030 (11) |
C17 | 0.0531 (17) | 0.0447 (15) | 0.0313 (14) | 0.0009 (12) | 0.0152 (13) | 0.0001 (11) |
C18 | 0.0291 (13) | 0.0448 (14) | 0.0322 (13) | −0.0001 (10) | 0.0053 (10) | −0.0109 (11) |
C19 | 0.0465 (16) | 0.0397 (14) | 0.0358 (14) | 0.0012 (11) | 0.0200 (12) | 0.0004 (11) |
C20 | 0.0292 (13) | 0.0431 (14) | 0.0281 (12) | 0.0003 (10) | 0.0024 (10) | 0.0015 (10) |
N1 | 0.0451 (15) | 0.0444 (14) | 0.0557 (17) | 0.0000 (11) | 0.0141 (13) | −0.0051 (13) |
N2 | 0.0242 (9) | 0.0254 (9) | 0.0289 (10) | −0.0003 (7) | 0.0032 (8) | −0.0026 (8) |
N3 | 0.0194 (9) | 0.0280 (9) | 0.0250 (10) | 0.0024 (7) | 0.0043 (7) | −0.0013 (7) |
N4 | 0.0272 (11) | 0.0335 (10) | 0.0393 (12) | −0.0019 (8) | 0.0051 (9) | −0.0037 (9) |
N5 | 0.0238 (10) | 0.0352 (10) | 0.0334 (11) | 0.0020 (8) | 0.0044 (8) | −0.0024 (9) |
O1 | 0.0655 (15) | 0.0591 (13) | 0.0405 (12) | 0.0144 (11) | 0.0052 (11) | 0.0087 (10) |
O2 | 0.0445 (11) | 0.0367 (10) | 0.0614 (14) | 0.0059 (8) | 0.0144 (10) | −0.0101 (9) |
O3 | 0.0419 (12) | 0.0608 (13) | 0.0496 (13) | 0.0099 (9) | 0.0177 (10) | −0.0103 (10) |
S1 | 0.0411 (4) | 0.0358 (3) | 0.0335 (3) | 0.0124 (2) | 0.0114 (3) | −0.0012 (3) |
OW1 | 0.0701 (18) | 0.0705 (17) | 0.083 (2) | 0.0168 (13) | 0.0392 (16) | 0.0159 (15) |
OW2 | 0.160 (4) | 0.0675 (19) | 0.082 (2) | −0.043 (2) | 0.024 (3) | −0.0034 (17) |
OW3 | 0.179 (4) | 0.240 (6) | 0.075 (3) | −0.151 (4) | 0.020 (3) | 0.016 (3) |
Ag1—N5 | 2.102 (2) | C11—N2 | 1.378 (3) |
Ag1—N4 | 2.103 (2) | C11—H11 | 0.9300 |
C1—N3i | 1.478 (3) | C12—C16 | 1.382 (4) |
C1—C3 | 1.511 (3) | C12—H12 | 0.9300 |
C1—H1AA | 0.9700 | C13—N5 | 1.328 (3) |
C1—H2AA | 0.9700 | C13—N3 | 1.336 (3) |
C2—C20 | 1.355 (4) | C13—H13 | 0.9300 |
C2—N3 | 1.369 (3) | C14—C16 | 1.380 (4) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C14 | 1.391 (3) | C15—H15 | 0.9300 |
C3—C6 | 1.404 (3) | C16—H16 | 0.9300 |
C4—N4 | 1.324 (3) | C17—C19 | 1.384 (4) |
C4—N2 | 1.339 (3) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—N4 | 1.378 (3) |
C5—C12 | 1.384 (4) | C18—H18 | 0.9300 |
C5—C6 | 1.387 (3) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—N5 | 1.373 (3) |
C6—C10 | 1.509 (3) | C20—H20 | 0.9300 |
C7—C19 | 1.380 (4) | N1—H1N | 0.85 (3) |
C7—C15 | 1.392 (4) | N1—H2N | 0.85 (3) |
C7—S1 | 1.761 (3) | N3—C1i | 1.478 (3) |
C8—C15 | 1.379 (4) | O1—S1 | 1.452 (2) |
C8—C9 | 1.395 (4) | O2—S1 | 1.459 (2) |
C8—H8 | 0.9300 | O3—S1 | 1.455 (2) |
C9—N1 | 1.380 (4) | OW1—H1B | 0.86 (5) |
C9—C17 | 1.393 (4) | OW1—H1A | 0.85 (4) |
C10—N2 | 1.471 (3) | OW2—H2A | 0.84 (5) |
C10—H10A | 0.9700 | OW2—H2B | 0.85 (4) |
C10—H10B | 0.9700 | OW3—H3A | 0.85 (5) |
C11—C18 | 1.348 (4) | OW3—H3B | 0.84 (7) |
N5—Ag1—N4 | 176.46 (9) | C16—C14—C3 | 121.1 (2) |
N3i—C1—C3 | 112.11 (19) | C16—C14—H14 | 119.4 |
N3i—C1—H1AA | 109.2 | C3—C14—H14 | 119.4 |
C3—C1—H1AA | 109.2 | C8—C15—C7 | 120.3 (3) |
N3i—C1—H2AA | 109.2 | C8—C15—H15 | 119.9 |
C3—C1—H2AA | 109.2 | C7—C15—H15 | 119.9 |
H1AA—C1—H2AA | 107.9 | C14—C16—C12 | 119.9 (2) |
C20—C2—N3 | 106.6 (2) | C14—C16—H16 | 120.0 |
C20—C2—H2 | 126.7 | C12—C16—H16 | 120.0 |
N3—C2—H2 | 126.7 | C19—C17—C9 | 121.3 (3) |
C14—C3—C6 | 119.0 (2) | C19—C17—H17 | 119.3 |
C14—C3—C1 | 118.1 (2) | C9—C17—H17 | 119.3 |
C6—C3—C1 | 122.9 (2) | C11—C18—N4 | 109.3 (2) |
N4—C4—N2 | 111.4 (2) | C11—C18—H18 | 125.3 |
N4—C4—H4 | 124.3 | N4—C18—H18 | 125.3 |
N2—C4—H4 | 124.3 | C7—C19—C17 | 120.7 (3) |
C12—C5—C6 | 121.2 (2) | C7—C19—H19 | 119.7 |
C12—C5—H5 | 119.4 | C17—C19—H19 | 119.7 |
C6—C5—H5 | 119.4 | C2—C20—N5 | 109.3 (2) |
C5—C6—C3 | 119.1 (2) | C2—C20—H20 | 125.4 |
C5—C6—C10 | 118.3 (2) | N5—C20—H20 | 125.4 |
C3—C6—C10 | 122.6 (2) | C9—N1—H1N | 115 (3) |
C19—C7—C15 | 118.8 (3) | C9—N1—H2N | 117 (3) |
C19—C7—S1 | 119.6 (2) | H1N—N1—H2N | 111 (4) |
C15—C7—S1 | 121.5 (2) | C4—N2—C11 | 106.9 (2) |
C15—C8—C9 | 121.7 (3) | C4—N2—C10 | 125.6 (2) |
C15—C8—H8 | 119.2 | C11—N2—C10 | 127.5 (2) |
C9—C8—H8 | 119.2 | C13—N3—C2 | 107.2 (2) |
N1—C9—C17 | 121.8 (3) | C13—N3—C1i | 125.4 (2) |
N1—C9—C8 | 120.9 (3) | C2—N3—C1i | 127.4 (2) |
C17—C9—C8 | 117.2 (3) | C4—N4—C18 | 105.7 (2) |
N2—C10—C6 | 112.10 (19) | C4—N4—Ag1 | 124.93 (18) |
N2—C10—H10A | 109.2 | C18—N4—Ag1 | 129.30 (18) |
C6—C10—H10A | 109.2 | C13—N5—C20 | 105.7 (2) |
N2—C10—H10B | 109.2 | C13—N5—Ag1 | 126.94 (18) |
C6—C10—H10B | 109.2 | C20—N5—Ag1 | 127.27 (17) |
H10A—C10—H10B | 107.9 | O1—S1—O3 | 113.29 (14) |
C18—C11—N2 | 106.7 (2) | O1—S1—O2 | 111.45 (14) |
C18—C11—H11 | 126.7 | O3—S1—O2 | 111.77 (13) |
N2—C11—H11 | 126.7 | O1—S1—C7 | 106.71 (14) |
C16—C12—C5 | 119.6 (2) | O3—S1—C7 | 106.10 (13) |
C16—C12—H12 | 120.2 | O2—S1—C7 | 107.04 (12) |
C5—C12—H12 | 120.2 | H1B—OW1—H1A | 106 (5) |
N5—C13—N3 | 111.3 (2) | H2A—OW2—H2B | 103 (5) |
N5—C13—H13 | 124.4 | H3A—OW3—H3B | 101 (9) |
N3—C13—H13 | 124.4 | ||
N3i—C1—C3—C14 | −100.7 (2) | N3—C2—C20—N5 | 0.4 (3) |
N3i—C1—C3—C6 | 80.3 (3) | N4—C4—N2—C11 | 0.3 (3) |
C12—C5—C6—C3 | 1.0 (4) | N4—C4—N2—C10 | −178.9 (2) |
C12—C5—C6—C10 | −178.9 (2) | C18—C11—N2—C4 | −0.1 (3) |
C14—C3—C6—C5 | −1.0 (3) | C18—C11—N2—C10 | 179.0 (2) |
C1—C3—C6—C5 | 178.0 (2) | C6—C10—N2—C4 | 128.4 (2) |
C14—C3—C6—C10 | 178.8 (2) | C6—C10—N2—C11 | −50.6 (3) |
C1—C3—C6—C10 | −2.1 (3) | N5—C13—N3—C2 | 0.5 (3) |
C15—C8—C9—N1 | 177.0 (3) | N5—C13—N3—C1i | 180.0 (2) |
C15—C8—C9—C17 | 0.0 (4) | C20—C2—N3—C13 | −0.5 (3) |
C5—C6—C10—N2 | 98.1 (2) | C20—C2—N3—C1i | −180.0 (2) |
C3—C6—C10—N2 | −81.7 (3) | N2—C4—N4—C18 | −0.3 (3) |
C6—C5—C12—C16 | −0.1 (4) | N2—C4—N4—Ag1 | 177.37 (15) |
C6—C3—C14—C16 | 0.2 (4) | C11—C18—N4—C4 | 0.3 (3) |
C1—C3—C14—C16 | −178.9 (2) | C11—C18—N4—Ag1 | −177.31 (18) |
C9—C8—C15—C7 | −0.3 (4) | N3—C13—N5—C20 | −0.3 (3) |
C19—C7—C15—C8 | 0.5 (4) | N3—C13—N5—Ag1 | −176.41 (15) |
S1—C7—C15—C8 | 177.7 (2) | C2—C20—N5—C13 | −0.1 (3) |
C3—C14—C16—C12 | 0.7 (4) | C2—C20—N5—Ag1 | 176.04 (17) |
C5—C12—C16—C14 | −0.8 (4) | C19—C7—S1—O1 | −155.0 (2) |
N1—C9—C17—C19 | −177.0 (3) | C15—C7—S1—O1 | 27.9 (2) |
C8—C9—C17—C19 | −0.1 (4) | C19—C7—S1—O3 | −33.9 (2) |
N2—C11—C18—N4 | −0.1 (3) | C15—C7—S1—O3 | 149.0 (2) |
C15—C7—C19—C17 | −0.6 (4) | C19—C7—S1—O2 | 85.6 (2) |
S1—C7—C19—C17 | −177.7 (2) | C15—C7—S1—O2 | −91.5 (2) |
C9—C17—C19—C7 | 0.3 (4) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···OW1ii | 0.85 (3) | 2.16 (3) | 3.003 (4) | 173 (4) |
OW1—H1A···OW2iii | 0.85 (4) | 1.95 (4) | 2.800 (5) | 175 (5) |
OW3—H3A···O3 | 0.85 (5) | 2.35 (9) | 2.815 (4) | 115 (8) |
OW1—H1B···O1 | 0.86 (5) | 2.12 (5) | 2.963 (4) | 171 (5) |
OW2—H2A···O2 | 0.84 (5) | 1.95 (5) | 2.775 (4) | 169 (7) |
Symmetry codes: (ii) −x, y, −z+3/2; (iii) −x+1/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(C14H14N4)2](C6H6NO3S)2·6H2O |
Mr | 1144.78 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.842 (3), 16.283 (3), 19.527 (4) |
β (°) | 104.76 (3) |
V (Å3) | 4563.6 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.02 |
Crystal size (mm) | 0.27 × 0.26 × 0.19 |
Data collection | |
Diffractometer | Rigaku RAXIS-RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.698, 0.811 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22007, 5221, 4333 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.091, 1.06 |
No. of reflections | 5221 |
No. of parameters | 324 |
No. of restraints | 11 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.91, −0.49 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···OW1i | 0.85 (3) | 2.16 (3) | 3.003 (4) | 173 (4) |
OW1—H1A···OW2ii | 0.85 (4) | 1.95 (4) | 2.800 (5) | 175 (5) |
OW3—H3A···O3 | 0.85 (5) | 2.35 (9) | 2.815 (4) | 115 (8) |
OW1—H1B···O1 | 0.86 (5) | 2.12 (5) | 2.963 (4) | 171 (5) |
OW2—H2A···O2 | 0.84 (5) | 1.95 (5) | 2.775 (4) | 169 (7) |
Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2. |
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Over the past decades, the design and synthesis of Ag(I) compounds have attracted great attention because of the versatility of their coordination geometries (Aakeröy & Beatty, 1998; Smith et al., 1996). In particular, silver-sulfonate complexes have attracted great attention by reason of their abilities to form inorganic-organic lamellar structures and intercalate guest molecules (Shimizu et al., 1998; Cote & Shimizu, 2004; Liu et al., 2007). In this paper, the synthesis and the crystal structure of a novel silver-sulfonate complex (I) [Ag2(IBI)2]L2 . 6H2O (IBI = 1,2-bis ((1H-imidazol-1-yl)methyl)benzene and L = p-aminobenzenesulfonic acid) is presented.
The molecular structure of (I) is shown in Fig.1. Selected bond distances and angles are listed in Table 1. The compound (I) shows a binuclear structure, where each of Ag(I) atoms has a slightly distorted linear geometry and is coordinated by two N atoms from the IBI ligands. The Ag—N (IBI) distances in (I) are near to that in the related compounds (Li et al., 2006). Notably, the L ligand does not coordinate to the Ag(I) center, acting as a counter-anion. Finally, N—H···O and O—H···O hydrogen bonds between water molecules and the L ligands result in the formation of a three-dimensional network (Table 2).