Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049550/ci2480sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049550/ci2480Isup2.hkl |
CCDC reference: 672671
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.020
- wR factor = 0.047
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.67
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 3626 Count of symmetry unique reflns 1944 Completeness (_total/calc) 186.52% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1682 Fraction of Friedel pairs measured 0.865 Are heavy atom types Z>Si present yes 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 ....... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
An aqueous solution (10 ml) of 7-aminonaphthalene-1-sulfonic acid (0.112 g, 0.5 mmol) was added to solid Ag2CO3 (0.069 g, 0.25 mmol) and stirred for several minutes until no further CO2 was given off. 2,3,5,6-tetramethylpyrazine (0.068 g, 0.5 mmol) in methanol (5 ml) was then added and a white precipitate formed. The precipitate was dissolved by dropwise addition of an aqueous solution of NH3 (14 M), and crystals of the title compound were obtained by slow evaporation of the solvent for several days at room temperature.
H atoms of the amino group were located in a difference map and refined isotropically with Uiso = 1.5Ueq(N). C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso = 1.2Ueq (C) for aromatic H atoms and C—H = 0.96 Å and Uiso = 1.5Ueq (C) for methyl H atoms. The maximum residual density peak is 0.71 Å from atom Ag1.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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).
[Ag(C10H8NO3S)(C8H12N2)] | F(000) = 944 |
Mr = 466.30 | Dx = 1.833 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: C -2yc | Cell parameters from 8199 reflections |
a = 10.101 (5) Å | θ = 3.2–27.5° |
b = 10.631 (6) Å | µ = 1.34 mm−1 |
c = 15.831 (7) Å | T = 293 K |
β = 96.180 (19)° | Block, yellow |
V = 1690.1 (15) Å3 | 0.21 × 0.16 × 0.15 mm |
Z = 4 |
Bruker APEX CCD area-detector diffractometer | 3626 independent reflections |
Radiation source: fine-focus sealed tube | 3534 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→13 |
Tmin = 0.765, Tmax = 0.808 | k = −13→13 |
8210 measured reflections | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.047 | w = 1/[σ2(Fo2) + (0.0278P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.002 |
3626 reflections | Δρmax = 0.51 e Å−3 |
245 parameters | Δρmin = −0.19 e Å−3 |
4 restraints | Absolute structure: Flack (1983), with 1687 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.001 (14) |
[Ag(C10H8NO3S)(C8H12N2)] | V = 1690.1 (15) Å3 |
Mr = 466.30 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 10.101 (5) Å | µ = 1.34 mm−1 |
b = 10.631 (6) Å | T = 293 K |
c = 15.831 (7) Å | 0.21 × 0.16 × 0.15 mm |
β = 96.180 (19)° |
Bruker APEX CCD area-detector diffractometer | 3626 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3534 reflections with I > 2σ(I) |
Tmin = 0.765, Tmax = 0.808 | Rint = 0.016 |
8210 measured reflections |
R[F2 > 2σ(F2)] = 0.020 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.047 | Δρmax = 0.51 e Å−3 |
S = 1.12 | Δρmin = −0.19 e Å−3 |
3626 reflections | Absolute structure: Flack (1983), with 1687 Friedel pairs |
245 parameters | Absolute structure parameter: −0.001 (14) |
4 restraints |
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 | 0.404494 (13) | 0.904978 (15) | 0.914016 (11) | 0.03466 (6) | |
C1 | 0.4695 (2) | 0.61273 (18) | 0.79933 (12) | 0.0199 (4) | |
C2 | 0.3599 (2) | 0.5415 (2) | 0.77423 (14) | 0.0275 (4) | |
H2 | 0.3126 | 0.5553 | 0.7214 | 0.033* | |
C3 | 0.3183 (2) | 0.4473 (2) | 0.82799 (17) | 0.0334 (5) | |
H3 | 0.2428 | 0.3998 | 0.8109 | 0.040* | |
C4 | 0.3888 (3) | 0.4256 (2) | 0.9052 (2) | 0.0306 (5) | |
H4 | 0.3600 | 0.3633 | 0.9403 | 0.037* | |
C5 | 0.5778 (2) | 0.4698 (2) | 1.01204 (13) | 0.0252 (4) | |
H5 | 0.5502 | 0.4054 | 1.0458 | 0.030* | |
C6 | 0.6894 (2) | 0.5382 (2) | 1.03999 (13) | 0.0246 (4) | |
C7 | 0.7290 (3) | 0.6356 (3) | 0.98737 (15) | 0.0304 (5) | |
H7 | 0.8041 | 0.6828 | 1.0058 | 0.037* | |
C8 | 0.6608 (2) | 0.6625 (2) | 0.91078 (14) | 0.0282 (4) | |
H8 | 0.6899 | 0.7274 | 0.8780 | 0.034* | |
C9 | 0.5449 (2) | 0.59244 (18) | 0.87993 (14) | 0.0214 (4) | |
C10 | 0.5043 (2) | 0.49545 (19) | 0.93312 (13) | 0.0228 (4) | |
C11 | 0.2410 (2) | 0.6798 (2) | 0.98876 (14) | 0.0240 (4) | |
C12 | 0.1527 (2) | 0.73938 (19) | 0.85327 (13) | 0.0237 (4) | |
C13 | 0.5543 (2) | 1.1474 (2) | 0.85442 (14) | 0.0215 (4) | |
C14 | 0.6417 (2) | 1.0872 (2) | 0.98955 (14) | 0.0246 (4) | |
C15 | 0.3439 (2) | 0.6982 (2) | 1.06260 (15) | 0.0329 (5) | |
H15A | 0.4058 | 0.7618 | 1.0491 | 0.049* | |
H15B | 0.3906 | 0.6206 | 1.0750 | 0.049* | |
H15C | 0.3016 | 0.7241 | 1.1112 | 0.049* | |
C16 | 0.1599 (2) | 0.8227 (2) | 0.77814 (14) | 0.0317 (5) | |
H16A | 0.2167 | 0.8931 | 0.7940 | 0.047* | |
H16B | 0.0723 | 0.8525 | 0.7584 | 0.047* | |
H16C | 0.1952 | 0.7763 | 0.7337 | 0.047* | |
C17 | 0.4499 (2) | 1.1309 (2) | 0.78121 (16) | 0.0318 (5) | |
H17A | 0.3824 | 1.0747 | 0.7970 | 0.048* | |
H17B | 0.4895 | 1.0964 | 0.7338 | 0.048* | |
H17C | 0.4107 | 1.2110 | 0.7657 | 0.048* | |
C18 | 0.6354 (3) | 1.0027 (3) | 1.06474 (16) | 0.0399 (6) | |
H18A | 0.5556 | 0.9532 | 1.0569 | 0.060* | |
H18B | 0.6352 | 1.0527 | 1.1152 | 0.060* | |
H18C | 0.7115 | 0.9480 | 1.0702 | 0.060* | |
N1 | 0.24569 (17) | 0.75411 (17) | 0.92050 (11) | 0.0233 (3) | |
N2 | 0.55020 (18) | 1.07168 (17) | 0.92248 (11) | 0.0234 (4) | |
N3 | 0.7676 (2) | 0.5116 (2) | 1.11496 (13) | 0.0350 (5) | |
H2N | 0.821 (3) | 0.565 (3) | 1.136 (2) | 0.052* | |
H1N | 0.730 (3) | 0.463 (3) | 1.147 (2) | 0.052* | |
O1 | 0.50658 (17) | 0.84893 (15) | 0.77532 (10) | 0.0309 (3) | |
O2 | 0.41660 (17) | 0.72625 (17) | 0.65422 (10) | 0.0353 (4) | |
O3 | 0.64820 (15) | 0.70373 (17) | 0.70974 (10) | 0.0313 (3) | |
S1 | 0.51364 (5) | 0.73176 (5) | 0.72854 (3) | 0.02202 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.03143 (8) | 0.03442 (9) | 0.03796 (9) | −0.01554 (8) | 0.00295 (6) | −0.00011 (8) |
C1 | 0.0198 (9) | 0.0185 (9) | 0.0214 (9) | 0.0009 (7) | 0.0016 (8) | −0.0010 (7) |
C2 | 0.0232 (10) | 0.0249 (10) | 0.0330 (11) | −0.0013 (8) | −0.0042 (9) | −0.0052 (9) |
C3 | 0.0262 (11) | 0.0250 (11) | 0.0478 (14) | −0.0111 (9) | −0.0021 (10) | −0.0014 (10) |
C4 | 0.0301 (14) | 0.0223 (9) | 0.0398 (14) | −0.0104 (10) | 0.0061 (11) | 0.0013 (10) |
C5 | 0.0314 (11) | 0.0207 (10) | 0.0244 (9) | −0.0020 (8) | 0.0071 (8) | 0.0031 (7) |
C6 | 0.0300 (10) | 0.0219 (10) | 0.0216 (9) | 0.0035 (8) | 0.0011 (8) | −0.0011 (8) |
C7 | 0.0295 (12) | 0.0336 (13) | 0.0270 (11) | −0.0130 (10) | −0.0023 (10) | 0.0027 (10) |
C8 | 0.0281 (10) | 0.0273 (11) | 0.0283 (9) | −0.0126 (8) | −0.0012 (9) | 0.0046 (8) |
C9 | 0.0208 (9) | 0.0212 (10) | 0.0221 (9) | −0.0024 (7) | 0.0020 (8) | −0.0026 (7) |
C10 | 0.0238 (9) | 0.0193 (9) | 0.0257 (10) | −0.0024 (8) | 0.0041 (8) | −0.0036 (7) |
C11 | 0.0220 (9) | 0.0244 (10) | 0.0257 (9) | 0.0004 (8) | 0.0028 (8) | −0.0073 (8) |
C12 | 0.0216 (9) | 0.0229 (10) | 0.0268 (9) | 0.0027 (8) | 0.0037 (8) | −0.0020 (8) |
C13 | 0.0178 (9) | 0.0199 (11) | 0.0266 (10) | 0.0020 (8) | 0.0010 (8) | −0.0038 (8) |
C14 | 0.0235 (10) | 0.0265 (11) | 0.0240 (10) | −0.0016 (8) | 0.0035 (9) | −0.0015 (8) |
C15 | 0.0268 (11) | 0.0403 (14) | 0.0302 (11) | −0.0030 (10) | −0.0027 (9) | −0.0074 (10) |
C16 | 0.0333 (11) | 0.0292 (11) | 0.0327 (11) | −0.0004 (9) | 0.0044 (9) | 0.0052 (9) |
C17 | 0.0321 (11) | 0.0260 (11) | 0.0344 (11) | −0.0022 (9) | −0.0100 (10) | 0.0000 (9) |
C18 | 0.0465 (14) | 0.0428 (14) | 0.0293 (11) | −0.0143 (11) | −0.0007 (11) | 0.0057 (10) |
N1 | 0.0200 (8) | 0.0235 (9) | 0.0269 (8) | −0.0029 (6) | 0.0051 (7) | −0.0063 (6) |
N2 | 0.0212 (8) | 0.0243 (9) | 0.0246 (9) | −0.0014 (7) | 0.0014 (7) | −0.0041 (6) |
N3 | 0.0430 (12) | 0.0343 (11) | 0.0254 (9) | −0.0045 (9) | −0.0062 (9) | 0.0040 (8) |
O1 | 0.0371 (8) | 0.0217 (8) | 0.0348 (8) | −0.0009 (6) | 0.0079 (7) | −0.0007 (6) |
O2 | 0.0335 (8) | 0.0437 (10) | 0.0263 (7) | 0.0006 (7) | −0.0075 (7) | 0.0048 (7) |
O3 | 0.0247 (7) | 0.0401 (9) | 0.0300 (8) | 0.0036 (7) | 0.0072 (6) | 0.0015 (6) |
S1 | 0.0213 (2) | 0.0240 (2) | 0.0205 (2) | 0.00127 (18) | 0.00097 (19) | 0.00122 (18) |
Ag1—N1 | 2.279 (2) | C12—C13i | 1.395 (3) |
Ag1—N2 | 2.298 (2) | C12—C16 | 1.491 (3) |
Ag1—O1 | 2.5936 (19) | C13—N2 | 1.349 (3) |
C1—C2 | 1.364 (3) | C13—C12ii | 1.395 (3) |
C1—C9 | 1.430 (3) | C13—C17 | 1.491 (3) |
C1—S1 | 1.779 (2) | C14—N2 | 1.341 (3) |
C2—C3 | 1.408 (3) | C14—C11ii | 1.406 (3) |
C2—H2 | 0.93 | C14—C18 | 1.498 (3) |
C3—C4 | 1.367 (4) | C15—H15A | 0.96 |
C3—H3 | 0.93 | C15—H15B | 0.96 |
C4—C10 | 1.414 (3) | C15—H15C | 0.96 |
C4—H4 | 0.93 | C16—H16A | 0.96 |
C5—C6 | 1.373 (3) | C16—H16B | 0.96 |
C5—C10 | 1.409 (3) | C16—H16C | 0.96 |
C5—H5 | 0.93 | C17—H17A | 0.96 |
C6—N3 | 1.383 (3) | C17—H17B | 0.96 |
C6—C7 | 1.414 (3) | C17—H17C | 0.96 |
C7—C8 | 1.359 (3) | C18—H18A | 0.96 |
C7—H7 | 0.93 | C18—H18B | 0.96 |
C8—C9 | 1.428 (3) | C18—H18C | 0.96 |
C8—H8 | 0.93 | N3—H2N | 0.83 (2) |
C9—C10 | 1.419 (3) | N3—H1N | 0.85 (2) |
C11—N1 | 1.343 (3) | O1—S1 | 1.4549 (18) |
C11—C14i | 1.406 (3) | O2—S1 | 1.4492 (17) |
C11—C15 | 1.491 (3) | O3—S1 | 1.4532 (17) |
C12—N1 | 1.351 (3) | ||
N1—Ag1—N2 | 171.76 (6) | N2—C14—C18 | 118.1 (2) |
N1—Ag1—O1 | 102.85 (6) | C11ii—C14—C18 | 121.2 (2) |
N2—Ag1—O1 | 85.19 (6) | C11—C15—H15A | 109.5 |
C2—C1—C9 | 120.92 (19) | C11—C15—H15B | 109.5 |
C2—C1—S1 | 117.51 (16) | H15A—C15—H15B | 109.5 |
C9—C1—S1 | 121.58 (15) | C11—C15—H15C | 109.5 |
C1—C2—C3 | 120.3 (2) | H15A—C15—H15C | 109.5 |
C1—C2—H2 | 119.9 | H15B—C15—H15C | 109.5 |
C3—C2—H2 | 119.9 | C12—C16—H16A | 109.5 |
C4—C3—C2 | 120.0 (2) | C12—C16—H16B | 109.5 |
C4—C3—H3 | 120.0 | H16A—C16—H16B | 109.5 |
C2—C3—H3 | 120.0 | C12—C16—H16C | 109.5 |
C3—C4—C10 | 121.6 (2) | H16A—C16—H16C | 109.5 |
C3—C4—H4 | 119.2 | H16B—C16—H16C | 109.5 |
C10—C4—H4 | 119.2 | C13—C17—H17A | 109.5 |
C6—C5—C10 | 121.25 (19) | C13—C17—H17B | 109.5 |
C6—C5—H5 | 119.4 | H17A—C17—H17B | 109.5 |
C10—C5—H5 | 119.4 | C13—C17—H17C | 109.5 |
C5—C6—N3 | 122.8 (2) | H17A—C17—H17C | 109.5 |
C5—C6—C7 | 118.17 (19) | H17B—C17—H17C | 109.5 |
N3—C6—C7 | 118.9 (2) | C14—C18—H18A | 109.5 |
C8—C7—C6 | 122.1 (2) | C14—C18—H18B | 109.5 |
C8—C7—H7 | 118.9 | H18A—C18—H18B | 109.5 |
C6—C7—H7 | 118.9 | C14—C18—H18C | 109.5 |
C7—C8—C9 | 120.9 (2) | H18A—C18—H18C | 109.5 |
C7—C8—H8 | 119.6 | H18B—C18—H18C | 109.5 |
C9—C8—H8 | 119.6 | C11—N1—C12 | 118.93 (19) |
C10—C9—C8 | 117.01 (19) | C11—N1—Ag1 | 122.42 (14) |
C10—C9—C1 | 118.60 (18) | C12—N1—Ag1 | 118.65 (15) |
C8—C9—C1 | 124.4 (2) | C14—N2—C13 | 118.76 (19) |
C5—C10—C4 | 120.9 (2) | C14—N2—Ag1 | 121.57 (14) |
C5—C10—C9 | 120.55 (18) | C13—N2—Ag1 | 119.22 (14) |
C4—C10—C9 | 118.5 (2) | C6—N3—H2N | 120 (3) |
N1—C11—C14i | 120.39 (19) | C6—N3—H1N | 113 (2) |
N1—C11—C15 | 118.1 (2) | H2N—N3—H1N | 119 (4) |
C14i—C11—C15 | 121.5 (2) | S1—O1—Ag1 | 132.33 (10) |
N1—C12—C13i | 120.4 (2) | O2—S1—O3 | 113.03 (10) |
N1—C12—C16 | 118.0 (2) | O2—S1—O1 | 112.46 (10) |
C13i—C12—C16 | 121.5 (2) | O3—S1—O1 | 112.21 (11) |
N2—C13—C12ii | 120.78 (19) | O2—S1—C1 | 106.81 (10) |
N2—C13—C17 | 118.1 (2) | O3—S1—C1 | 106.66 (10) |
C12ii—C13—C17 | 121.1 (2) | O1—S1—C1 | 105.01 (10) |
N2—C14—C11ii | 120.7 (2) | ||
C9—C1—C2—C3 | 0.7 (3) | C13i—C12—N1—C11 | −0.8 (3) |
S1—C1—C2—C3 | −178.85 (18) | C16—C12—N1—C11 | −179.95 (19) |
C1—C2—C3—C4 | −0.9 (4) | C13i—C12—N1—Ag1 | 179.48 (15) |
C2—C3—C4—C10 | −0.3 (4) | C16—C12—N1—Ag1 | 0.3 (2) |
C10—C5—C6—N3 | −176.6 (2) | O1—Ag1—N1—C11 | 125.56 (16) |
C10—C5—C6—C7 | 0.0 (3) | O1—Ag1—N1—C12 | −54.73 (16) |
C5—C6—C7—C8 | −0.3 (4) | C11ii—C14—N2—C13 | −0.6 (3) |
N3—C6—C7—C8 | 176.5 (2) | C18—C14—N2—C13 | 179.8 (2) |
C6—C7—C8—C9 | 0.0 (4) | C11ii—C14—N2—Ag1 | 171.63 (15) |
C7—C8—C9—C10 | 0.7 (4) | C18—C14—N2—Ag1 | −8.0 (3) |
C7—C8—C9—C1 | −178.5 (2) | C12ii—C13—N2—C14 | 0.6 (3) |
C2—C1—C9—C10 | 0.7 (3) | C17—C13—N2—C14 | −178.6 (2) |
S1—C1—C9—C10 | −179.75 (15) | C12ii—C13—N2—Ag1 | −171.77 (15) |
C2—C1—C9—C8 | 179.8 (2) | C17—C13—N2—Ag1 | 9.0 (3) |
S1—C1—C9—C8 | −0.6 (3) | O1—Ag1—N2—C14 | −121.18 (17) |
C6—C5—C10—C4 | −179.3 (2) | O1—Ag1—N2—C13 | 50.99 (16) |
C6—C5—C10—C9 | 0.6 (3) | N1—Ag1—O1—S1 | −24.43 (14) |
C3—C4—C10—C5 | −178.4 (2) | N2—Ag1—O1—S1 | 157.43 (14) |
C3—C4—C10—C9 | 1.7 (4) | Ag1—O1—S1—O2 | 102.13 (14) |
C8—C9—C10—C5 | −0.9 (3) | Ag1—O1—S1—O3 | −129.12 (12) |
C1—C9—C10—C5 | 178.25 (19) | Ag1—O1—S1—C1 | −13.64 (15) |
C8—C9—C10—C4 | 179.0 (2) | C2—C1—S1—O2 | −0.2 (2) |
C1—C9—C10—C4 | −1.9 (3) | C9—C1—S1—O2 | −179.73 (17) |
C14i—C11—N1—C12 | 0.9 (3) | C2—C1—S1—O3 | −121.29 (18) |
C15—C11—N1—C12 | −179.54 (19) | C9—C1—S1—O3 | 59.14 (19) |
C14i—C11—N1—Ag1 | −179.44 (15) | C2—C1—S1—O1 | 119.45 (18) |
C15—C11—N1—Ag1 | 0.2 (3) | C9—C1—S1—O1 | −60.11 (19) |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x+1/2, y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N···O3iii | 0.85 (2) | 2.23 (3) | 3.055 (3) | 165 (4) |
N3—H2N···O2iv | 0.83 (2) | 2.43 (3) | 3.197 (3) | 155 (3) |
C16—H16B···Cg1v | 0.96 | 2.65 | 3.425 (3) | 138 |
Symmetry codes: (iii) x, −y+1, z+1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) x−1/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C10H8NO3S)(C8H12N2)] |
Mr | 466.30 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 10.101 (5), 10.631 (6), 15.831 (7) |
β (°) | 96.180 (19) |
V (Å3) | 1690.1 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.34 |
Crystal size (mm) | 0.21 × 0.16 × 0.15 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.765, 0.808 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8210, 3626, 3534 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.020, 0.047, 1.12 |
No. of reflections | 3626 |
No. of parameters | 245 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.51, −0.19 |
Absolute structure | Flack (1983), with 1687 Friedel pairs |
Absolute structure parameter | −0.001 (14) |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
Ag1—N1 | 2.279 (2) | Ag1—O1 | 2.5936 (19) |
Ag1—N2 | 2.298 (2) | ||
N1—Ag1—N2 | 171.76 (6) | N2—Ag1—O1 | 85.19 (6) |
N1—Ag1—O1 | 102.85 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N···O3i | 0.85 (2) | 2.23 (3) | 3.055 (3) | 165 (4) |
N3—H2N···O2ii | 0.83 (2) | 2.43 (3) | 3.197 (3) | 155 (3) |
C16—H16B···Cg1iii | 0.96 | 2.65 | 3.425 (3) | 138 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x+1/2, −y+3/2, z+1/2; (iii) x−1/2, y+1/2, z. |
As part of an investigation of the transition metal application there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound is described.
As shown in Fig. 1, the AgI ion is three coordinated by two N atoms from two 2,3,5,6-tetramethylpyrazine ligands and one O atom from a 7-aminonaphthalene-1-sulfonate anion. Each 2,3,5,6-tetramethylpyrazine ligand coordinates to two AgI cations through its two aromatic N atoms, thus acing as a bridging bidentate ligand. The AgI cations are bridged by 2,3,5,6-tetramethylpyrazine ligands to a chain structure. In the chain, face-to-face π–π interaction is observed between the naphthalene ring system and the adjacent pyrazine ring, with a ring centroid-to-centriod distance of 3.517 (1) Å. (Fig. 2). Intermolecular N—H···O hydrogen bonds (Table 2) involving the amino N atom and two sulfonate O atoms of two adjacent 7-aminonaphthalene-1-sulfonate anions link the chains into a three-dimensional framework (Fig. 3). A C—H···π interaction (Table 2) between a methyl group of the 2,3,5,6-tetramethylpyrazine ligand and the C1–C4/C10/C9 benzene ring (centroid Cg1) of the adjacent naphthalene ring system further stabilize the three-dimensional framework.