Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103001914/na1589sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103001914/na1589Isup2.hkl |
CCDC reference: 207998
To a solution of chloro(triphenylphosphine)gold(I) (0.2 mmol) in methanol (5 ml), sulfadiazine (0.1 mmol) in methanol (Volume?) and triethylamine (0.1 mmol) were added. The mixture was stirred under reflux for 2 h and cooled to room temperature, and the solid was separated by filtration (yield 85% based on sulfadiazine). Recrystallization from dichloromethane and petroleum ether (Ratio?) afforded crystals of the pure product, (I), after two weeks. Elemental analysis (calculated/found): C 47.46/47.08%, H 3.42/3.43%, N 7.90/7.66%.
H atoms were constrained to riding positions with C—H distances of 0.93 Å Is this change OK?, except for the two on N44, which were allowed to refine freely.
Data collection: Bruker software Please provide full details; cell refinement: Bruker software Please provide full details; data reduction: Bruker software Please provide full details; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. A view of the molecule of (I) with the atomic labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity. |
[Au(C10H9N4O2S)(C18H15P)] | F(000) = 1384 |
Mr = 708.51 | Dx = 1.838 Mg m−3 |
Monoclinic, P21/c | Melting point: 0 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71069 Å |
a = 11.878 (5) Å | Cell parameters from 7802 reflections |
b = 13.329 (5) Å | θ = 1.8–30.8° |
c = 16.677 (5) Å | µ = 5.92 mm−1 |
β = 104.085 (5)° | T = 293 K |
V = 2561.0 (16) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.19 × 0.13 mm |
Bruker Model CCD area-detector diffractometer | 6618 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 30.6°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.288, Tmax = 0.463 | k = −19→19 |
31145 measured reflections | l = −23→23 |
7802 independent 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)] = 0.019 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0236P)2] where P = (Fo2 + 2Fc2)/3 |
7802 reflections | (Δ/σ)max = 0.002 |
342 parameters | Δρmax = 1.15 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
[Au(C10H9N4O2S)(C18H15P)] | V = 2561.0 (16) Å3 |
Mr = 708.51 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.878 (5) Å | µ = 5.92 mm−1 |
b = 13.329 (5) Å | T = 293 K |
c = 16.677 (5) Å | 0.25 × 0.19 × 0.13 mm |
β = 104.085 (5)° |
Bruker Model CCD area-detector diffractometer | 7802 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6618 reflections with I > 2σ(I) |
Tmin = 0.288, Tmax = 0.463 | Rint = 0.029 |
31145 measured reflections |
R[F2 > 2σ(F2)] = 0.019 | 0 restraints |
wR(F2) = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 1.15 e Å−3 |
7802 reflections | Δρmin = −0.54 e Å−3 |
342 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 | ||
Au | 0.656917 (7) | 0.155522 (6) | 0.194110 (5) | 0.01488 (3) | |
P | 0.51967 (5) | 0.06351 (4) | 0.22946 (3) | 0.01384 (10) | |
C1 | 0.41685 (18) | 0.00460 (15) | 0.14428 (13) | 0.0158 (4) | |
C2 | 0.40778 (18) | 0.03882 (16) | 0.06376 (13) | 0.0181 (4) | |
H2 | 0.4525 | 0.0929 | 0.0546 | 0.022* | |
C3 | 0.33209 (19) | −0.00766 (18) | −0.00270 (13) | 0.0226 (5) | |
H3 | 0.3266 | 0.0151 | −0.0562 | 0.027* | |
C4 | 0.2650 (2) | −0.08779 (18) | 0.01085 (15) | 0.0251 (5) | |
H4 | 0.2151 | −0.1192 | −0.0337 | 0.03* | |
C5 | 0.2716 (2) | −0.12147 (18) | 0.09039 (15) | 0.0261 (5) | |
H5 | 0.2251 | −0.1744 | 0.0993 | 0.031* | |
C6 | 0.34796 (19) | −0.07594 (17) | 0.15684 (14) | 0.0220 (5) | |
H6 | 0.3532 | −0.0993 | 0.2102 | 0.026* | |
C11 | 0.43587 (19) | 0.13134 (16) | 0.28905 (13) | 0.0171 (4) | |
C12 | 0.4929 (2) | 0.20560 (18) | 0.34218 (14) | 0.0241 (5) | |
H12 | 0.5706 | 0.2191 | 0.3448 | 0.029* | |
C13 | 0.4360 (3) | 0.2598 (2) | 0.39120 (16) | 0.0327 (6) | |
H13 | 0.4753 | 0.3092 | 0.4266 | 0.039* | |
C14 | 0.3213 (2) | 0.2404 (2) | 0.38746 (15) | 0.0327 (6) | |
H14 | 0.283 | 0.2766 | 0.4205 | 0.039* | |
C15 | 0.2629 (2) | 0.1676 (2) | 0.33508 (16) | 0.0330 (6) | |
H15 | 0.1853 | 0.1546 | 0.3331 | 0.04* | |
C16 | 0.3189 (2) | 0.1130 (2) | 0.28489 (15) | 0.0263 (5) | |
H16 | 0.2786 | 0.0647 | 0.2489 | 0.032* | |
C21 | 0.58780 (17) | −0.03976 (15) | 0.29467 (12) | 0.0152 (4) | |
C22 | 0.69602 (19) | −0.07500 (16) | 0.28732 (13) | 0.0188 (4) | |
H22 | 0.734 | −0.0428 | 0.252 | 0.023* | |
C23 | 0.7468 (2) | −0.15789 (17) | 0.33256 (14) | 0.0228 (5) | |
H23 | 0.8185 | −0.1811 | 0.3275 | 0.027* | |
C24 | 0.6898 (2) | −0.20615 (16) | 0.38562 (14) | 0.0217 (5) | |
H24 | 0.7233 | −0.2621 | 0.4154 | 0.026* | |
C25 | 0.5832 (2) | −0.17082 (16) | 0.39405 (14) | 0.0213 (5) | |
H25 | 0.5458 | −0.2028 | 0.4299 | 0.026* | |
C26 | 0.53242 (19) | −0.08785 (16) | 0.34909 (13) | 0.0180 (4) | |
H26 | 0.4613 | −0.0642 | 0.3552 | 0.022* | |
N | 0.80060 (15) | 0.23046 (13) | 0.17456 (11) | 0.0173 (4) | |
C31 | 0.79122 (19) | 0.31454 (16) | 0.12459 (13) | 0.0178 (4) | |
N32 | 0.88187 (18) | 0.37703 (16) | 0.13279 (13) | 0.0268 (4) | |
C33 | 0.8673 (2) | 0.45374 (19) | 0.07949 (17) | 0.0343 (6) | |
H33 | 0.9289 | 0.4978 | 0.0824 | 0.041* | |
C34 | 0.7660 (2) | 0.4706 (2) | 0.02083 (17) | 0.0344 (6) | |
H34 | 0.7581 | 0.5236 | −0.0164 | 0.041* | |
C35 | 0.6764 (2) | 0.40417 (19) | 0.02042 (15) | 0.0283 (5) | |
H35 | 0.6055 | 0.4146 | −0.0173 | 0.034* | |
N36 | 0.68677 (17) | 0.32592 (14) | 0.07146 (12) | 0.0227 (4) | |
S | 0.92547 (5) | 0.18562 (4) | 0.22536 (3) | 0.01684 (10) | |
O1 | 1.01158 (14) | 0.20031 (13) | 0.17878 (10) | 0.0231 (3) | |
O2 | 0.90231 (14) | 0.08390 (11) | 0.24586 (10) | 0.0225 (3) | |
C41 | 0.96986 (18) | 0.25159 (16) | 0.31911 (13) | 0.0169 (4) | |
C42 | 0.96067 (18) | 0.20450 (17) | 0.39281 (13) | 0.0183 (4) | |
H42 | 0.9284 | 0.1408 | 0.3912 | 0.022* | |
C43 | 0.99970 (19) | 0.25319 (17) | 0.46733 (14) | 0.0207 (4) | |
H43 | 0.9943 | 0.2215 | 0.5159 | 0.025* | |
C44 | 1.04781 (19) | 0.35057 (16) | 0.47091 (13) | 0.0186 (4) | |
C45 | 1.05386 (19) | 0.39625 (17) | 0.39597 (13) | 0.0204 (4) | |
H45 | 1.0834 | 0.461 | 0.3968 | 0.025* | |
C46 | 1.01685 (19) | 0.34703 (17) | 0.32103 (14) | 0.0201 (4) | |
H46 | 1.0235 | 0.3778 | 0.2723 | 0.024* | |
N44 | 1.0867 (2) | 0.39766 (17) | 0.54478 (13) | 0.0284 (5) | |
H44A | 1.070 (3) | 0.375 (2) | 0.5933 (19) | 0.040 (8)* | |
H44B | 1.110 (3) | 0.460 (2) | 0.5454 (17) | 0.036 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au | 0.01356 (4) | 0.01590 (4) | 0.01537 (4) | −0.00328 (3) | 0.00391 (3) | −0.00010 (3) |
P | 0.0126 (2) | 0.0146 (2) | 0.0144 (2) | −0.00131 (19) | 0.00350 (19) | 0.00070 (19) |
C1 | 0.0136 (9) | 0.0157 (9) | 0.0171 (9) | 0.0008 (7) | 0.0017 (8) | −0.0008 (7) |
C2 | 0.0159 (10) | 0.0190 (10) | 0.0201 (10) | 0.0009 (8) | 0.0056 (8) | −0.0002 (8) |
C3 | 0.0210 (11) | 0.0299 (12) | 0.0154 (10) | 0.0043 (9) | 0.0015 (8) | −0.0033 (9) |
C4 | 0.0191 (11) | 0.0243 (12) | 0.0266 (12) | 0.0028 (9) | −0.0047 (9) | −0.0106 (9) |
C5 | 0.0197 (11) | 0.0200 (11) | 0.0348 (13) | −0.0051 (9) | −0.0010 (10) | −0.0002 (10) |
C6 | 0.0191 (11) | 0.0210 (11) | 0.0235 (11) | −0.0037 (9) | 0.0004 (9) | 0.0047 (9) |
C11 | 0.0175 (10) | 0.0175 (10) | 0.0173 (10) | 0.0046 (8) | 0.0064 (8) | 0.0043 (8) |
C12 | 0.0273 (12) | 0.0237 (12) | 0.0239 (11) | −0.0017 (9) | 0.0115 (10) | −0.0037 (9) |
C13 | 0.0470 (16) | 0.0272 (13) | 0.0289 (13) | 0.0025 (12) | 0.0190 (12) | −0.0070 (10) |
C14 | 0.0436 (16) | 0.0353 (14) | 0.0248 (12) | 0.0195 (12) | 0.0190 (11) | 0.0079 (11) |
C15 | 0.0206 (12) | 0.0509 (17) | 0.0301 (13) | 0.0144 (11) | 0.0111 (10) | 0.0100 (12) |
C16 | 0.0157 (11) | 0.0382 (14) | 0.0257 (12) | 0.0037 (10) | 0.0060 (9) | 0.0009 (10) |
C21 | 0.0149 (9) | 0.0144 (9) | 0.0160 (9) | −0.0010 (8) | 0.0028 (7) | −0.0014 (7) |
C22 | 0.0171 (10) | 0.0192 (10) | 0.0211 (10) | 0.0013 (8) | 0.0065 (8) | −0.0004 (8) |
C23 | 0.0215 (11) | 0.0208 (11) | 0.0254 (11) | 0.0055 (9) | 0.0044 (9) | −0.0040 (9) |
C24 | 0.0251 (12) | 0.0147 (10) | 0.0236 (11) | 0.0021 (9) | 0.0025 (9) | 0.0001 (8) |
C25 | 0.0251 (12) | 0.0181 (11) | 0.0201 (10) | −0.0029 (9) | 0.0042 (9) | 0.0051 (8) |
C26 | 0.0153 (10) | 0.0196 (10) | 0.0186 (10) | −0.0012 (8) | 0.0032 (8) | 0.0015 (8) |
N | 0.0149 (8) | 0.0202 (9) | 0.0164 (8) | −0.0032 (7) | 0.0030 (7) | 0.0024 (7) |
C31 | 0.0197 (10) | 0.0182 (10) | 0.0168 (10) | −0.0023 (8) | 0.0067 (8) | −0.0016 (8) |
N32 | 0.0248 (11) | 0.0234 (10) | 0.0311 (11) | −0.0078 (8) | 0.0049 (9) | 0.0035 (8) |
C33 | 0.0331 (14) | 0.0270 (13) | 0.0433 (15) | −0.0075 (11) | 0.0102 (12) | 0.0075 (11) |
C34 | 0.0435 (16) | 0.0252 (13) | 0.0347 (14) | 0.0021 (12) | 0.0100 (12) | 0.0123 (11) |
C35 | 0.0265 (13) | 0.0290 (13) | 0.0272 (12) | 0.0030 (10) | 0.0025 (10) | 0.0057 (10) |
N36 | 0.0213 (10) | 0.0232 (10) | 0.0232 (10) | 0.0001 (8) | 0.0049 (8) | 0.0033 (8) |
S | 0.0144 (2) | 0.0177 (2) | 0.0189 (2) | −0.00074 (19) | 0.00485 (19) | −0.00249 (19) |
O1 | 0.0186 (8) | 0.0297 (9) | 0.0235 (8) | −0.0018 (7) | 0.0099 (6) | −0.0059 (7) |
O2 | 0.0227 (8) | 0.0164 (8) | 0.0272 (8) | 0.0007 (6) | 0.0038 (7) | −0.0012 (6) |
C41 | 0.0132 (9) | 0.0192 (10) | 0.0185 (10) | 0.0013 (8) | 0.0040 (8) | −0.0018 (8) |
C42 | 0.0157 (10) | 0.0188 (10) | 0.0207 (10) | 0.0023 (8) | 0.0048 (8) | −0.0007 (8) |
C43 | 0.0194 (11) | 0.0242 (11) | 0.0187 (10) | 0.0032 (9) | 0.0048 (8) | 0.0022 (8) |
C44 | 0.0177 (10) | 0.0213 (10) | 0.0176 (10) | 0.0024 (8) | 0.0059 (8) | −0.0005 (8) |
C45 | 0.0208 (11) | 0.0197 (11) | 0.0211 (11) | −0.0023 (9) | 0.0056 (9) | −0.0019 (8) |
C46 | 0.0176 (10) | 0.0227 (11) | 0.0205 (10) | 0.0003 (9) | 0.0059 (8) | 0.0010 (9) |
N44 | 0.0374 (13) | 0.0276 (12) | 0.0211 (10) | −0.0067 (10) | 0.0090 (9) | −0.0017 (9) |
Au—N | 2.0707 (18) | C23—H23 | 0.93 |
Au—P | 2.2310 (8) | C24—C25 | 1.390 (3) |
Au—O2 | 2.9880 (19) | C24—H24 | 0.93 |
Au—N36 | 3.134 (2) | C25—C26 | 1.389 (3) |
P—C11 | 1.810 (2) | C25—H25 | 0.93 |
P—C1 | 1.812 (2) | C26—H26 | 0.93 |
P—C21 | 1.818 (2) | N—C31 | 1.385 (3) |
C1—C6 | 1.396 (3) | N—S | 1.6320 (19) |
C1—C2 | 1.397 (3) | C31—N32 | 1.342 (3) |
C2—C3 | 1.391 (3) | C31—N36 | 1.346 (3) |
C2—H2 | 0.93 | N32—C33 | 1.338 (3) |
C3—C4 | 1.384 (3) | C33—C34 | 1.372 (4) |
C3—H3 | 0.93 | C33—H33 | 0.93 |
C4—C5 | 1.384 (3) | C34—C35 | 1.384 (4) |
C4—H4 | 0.93 | C34—H34 | 0.93 |
C5—C6 | 1.389 (3) | C35—N36 | 1.333 (3) |
C5—H5 | 0.93 | C35—H35 | 0.93 |
C6—H6 | 0.93 | S—O1 | 1.4405 (16) |
C11—C12 | 1.390 (3) | S—O2 | 1.4410 (17) |
C11—C16 | 1.395 (3) | S—C41 | 1.759 (2) |
C12—C13 | 1.385 (3) | C41—C46 | 1.386 (3) |
C12—H12 | 0.93 | C41—C42 | 1.408 (3) |
C13—C14 | 1.372 (4) | C42—C43 | 1.378 (3) |
C13—H13 | 0.93 | C42—H42 | 0.93 |
C14—C15 | 1.376 (4) | C43—C44 | 1.413 (3) |
C14—H14 | 0.93 | C43—H43 | 0.93 |
C15—C16 | 1.394 (3) | C44—N44 | 1.359 (3) |
C15—H15 | 0.93 | C44—C45 | 1.408 (3) |
C16—H16 | 0.93 | C45—C46 | 1.385 (3) |
C21—C26 | 1.399 (3) | C45—H45 | 0.93 |
C21—C22 | 1.402 (3) | C46—H46 | 0.93 |
C22—C23 | 1.390 (3) | N44—H44A | 0.93 (3) |
C22—H22 | 0.93 | N44—H44B | 0.88 (3) |
C23—C24 | 1.395 (3) | ||
N—Au—P | 171.93 (5) | C25—C24—C23 | 120.2 (2) |
N—Au—O2 | 54.28 (6) | C25—C24—H24 | 119.9 |
P—Au—O2 | 118.18 (4) | C23—C24—H24 | 119.9 |
N—Au—N36 | 47.09 (6) | C26—C25—C24 | 120.1 (2) |
P—Au—N36 | 140.98 (4) | C26—C25—H25 | 119.9 |
O2—Au—N36 | 99.36 (5) | C24—C25—H25 | 119.9 |
C11—P—C1 | 106.93 (10) | C25—C26—C21 | 120.3 (2) |
C11—P—C21 | 105.90 (10) | C25—C26—H26 | 119.9 |
C1—P—C21 | 104.95 (10) | C21—C26—H26 | 119.9 |
C11—P—Au | 113.91 (8) | C31—N—S | 122.60 (15) |
C1—P—Au | 115.31 (7) | C31—N—Au | 122.44 (14) |
C21—P—Au | 109.07 (7) | S—N—Au | 114.92 (10) |
C6—C1—C2 | 119.0 (2) | N32—C31—N36 | 125.8 (2) |
C6—C1—P | 121.56 (16) | N32—C31—N | 119.7 (2) |
C2—C1—P | 119.46 (16) | N36—C31—N | 114.43 (19) |
C3—C2—C1 | 120.3 (2) | C33—N32—C31 | 115.8 (2) |
C3—C2—H2 | 119.9 | N32—C33—C34 | 123.2 (2) |
C1—C2—H2 | 119.9 | N32—C33—H33 | 118.4 |
C4—C3—C2 | 120.0 (2) | C34—C33—H33 | 118.4 |
C4—C3—H3 | 120 | C33—C34—C35 | 116.0 (2) |
C2—C3—H3 | 120 | C33—C34—H34 | 122 |
C3—C4—C5 | 120.4 (2) | C35—C34—H34 | 122 |
C3—C4—H4 | 119.8 | N36—C35—C34 | 123.1 (2) |
C5—C4—H4 | 119.8 | N36—C35—H35 | 118.4 |
C4—C5—C6 | 119.8 (2) | C34—C35—H35 | 118.4 |
C4—C5—H5 | 120.1 | C35—N36—C31 | 115.8 (2) |
C6—C5—H5 | 120.1 | C35—N36—Au | 167.52 (16) |
C5—C6—C1 | 120.6 (2) | C31—N36—Au | 73.82 (12) |
C5—C6—H6 | 119.7 | O1—S—O2 | 117.22 (10) |
C1—C6—H6 | 119.7 | O1—S—N | 110.19 (10) |
C12—C11—C16 | 118.8 (2) | O2—S—N | 105.42 (10) |
C12—C11—P | 117.24 (17) | O1—S—C41 | 108.23 (10) |
C16—C11—P | 123.98 (18) | O2—S—C41 | 107.02 (10) |
C13—C12—C11 | 121.0 (2) | N—S—C41 | 108.44 (10) |
C13—C12—H12 | 119.5 | S—O2—Au | 81.95 (7) |
C11—C12—H12 | 119.5 | C46—C41—C42 | 120.3 (2) |
C14—C13—C12 | 119.8 (3) | C46—C41—S | 120.74 (16) |
C14—C13—H13 | 120.1 | C42—C41—S | 118.88 (16) |
C12—C13—H13 | 120.1 | C43—C42—C41 | 119.8 (2) |
C13—C14—C15 | 120.2 (2) | C43—C42—H42 | 120.1 |
C13—C14—H14 | 119.9 | C41—C42—H42 | 120.1 |
C15—C14—H14 | 119.9 | C42—C43—C44 | 120.9 (2) |
C14—C15—C16 | 120.6 (2) | C42—C43—H43 | 119.5 |
C14—C15—H15 | 119.7 | C44—C43—H43 | 119.5 |
C16—C15—H15 | 119.7 | N44—C44—C45 | 121.7 (2) |
C15—C16—C11 | 119.6 (2) | N44—C44—C43 | 120.4 (2) |
C15—C16—H16 | 120.2 | C45—C44—C43 | 117.9 (2) |
C11—C16—H16 | 120.2 | C46—C45—C44 | 121.5 (2) |
C26—C21—C22 | 119.3 (2) | C46—C45—H45 | 119.2 |
C26—C21—P | 121.59 (16) | C44—C45—H45 | 119.2 |
C22—C21—P | 119.06 (16) | C45—C46—C41 | 119.5 (2) |
C23—C22—C21 | 120.3 (2) | C45—C46—H46 | 120.2 |
C23—C22—H22 | 119.8 | C41—C46—H46 | 120.2 |
C21—C22—H22 | 119.8 | C44—N44—H44A | 123 (2) |
C22—C23—C24 | 119.8 (2) | C44—N44—H44B | 119.0 (19) |
C22—C23—H23 | 120.1 | H44A—N44—H44B | 115 (3) |
C24—C23—H23 | 120.1 | ||
C31—N—S—C41 | 84.45 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N44—H44A···O1i | 0.93 (3) | 2.00 (3) | 2.909 (3) | 165 (3) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Au(C10H9N4O2S)(C18H15P)] |
Mr | 708.51 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.878 (5), 13.329 (5), 16.677 (5) |
β (°) | 104.085 (5) |
V (Å3) | 2561.0 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 5.92 |
Crystal size (mm) | 0.25 × 0.19 × 0.13 |
Data collection | |
Diffractometer | Bruker Model CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.288, 0.463 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31145, 7802, 6618 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.715 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.019, 0.045, 1.02 |
No. of reflections | 7802 |
No. of parameters | 342 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.15, −0.54 |
Computer programs: Bruker software Please provide full details, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.
Au—N | 2.0707 (18) | N—S | 1.6320 (19) |
Au—P | 2.2310 (8) | S—O1 | 1.4405 (16) |
Au—O2 | 2.9880 (19) | S—O2 | 1.4410 (17) |
Au—N36 | 3.134 (2) | S—C41 | 1.759 (2) |
N—Au—P | 171.93 (5) | O1—S—O2 | 117.22 (10) |
N—Au—O2 | 54.28 (6) | O1—S—N | 110.19 (10) |
P—Au—O2 | 118.18 (4) | O2—S—N | 105.42 (10) |
N—Au—N36 | 47.09 (6) | O1—S—C41 | 108.23 (10) |
P—Au—N36 | 140.98 (4) | O2—S—C41 | 107.02 (10) |
C31—N—S | 122.60 (15) | N—S—C41 | 108.44 (10) |
C31—N—Au | 122.44 (14) | S—O2—Au | 81.95 (7) |
S—N—Au | 114.92 (10) | ||
C31—N—S—C41 | 84.45 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N44—H44A···O1i | 0.93 (3) | 2.00 (3) | 2.909 (3) | 165 (3) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Metal complexes of 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide (sulfadiazine) are widely used to prevent bacterial infection in both humans and animals during the treatment of burns (Yuan et al., 2001). The effectiveness of these complexes for burn treatment depends on the presence of both the metal ion and the free ligand (Baenziger et al., 1983; Raso et al., 1997). Gold(I) complexes have found use in medicine, with those containing sulfur ligands being used for the treatment of rheumatoid arthritis (Shaw, 1999; Ahmad et al., 2002). Despite the varied structural chemistry of sulfadizine and its derivatives (Baenziger & Struss, 1976; Gutiérrez et al., 2001), gold(I) complexes with these ligands have not been reported to date. In this context, we report the preparation and structural characterization of, and some observations on, the title compound, (I), also known as sulfadiazinato(triphenylphosphine)gold(I). \sch
Single crystals of (I) were obtained by recrystallization from dichloromethane and petroleum ether of the crude product from the reaction of chloro(triphenylphosphine)gold(I), sulfadiazine and triethylamine in methanol. The asymmetric unit contains a complete molecule (Fig. 1) of the compound. Selected bond distances and angles are given in Table 1.
Compound (I) shows a nearly linear AuI N—Au—P geometry with normal distances. The Au atom shows weak interactions with atoms O2 and N36 from the sulfadiazinate ligand. The sulfadiazinate N atom bonded to Au shows trigonal planar geometry, with atom N lying 0.020 (2) Å out of the plane defined by atoms Au, S and C31. The pyrimidine ring is rotated slightly with respect to the plane of the N atom by 18.2 (11)°. The sulfonamide group is approximately tetrahedral, with the largest deviation being in the O1—S—O2 angle.
Atom O1 of the sulfonamide group participates in intermolecular hydrogen bonding to the amino group (Table 2). The same pattern is observed in the structure of sulfadiazine (Ihn et al., 1975; Kokila et al., 1995). This intermolecular hydrogen bond to the neighbouring molecule forms continuous chains along the c axis.
The two ring systems in the sulfadiazinate ligand of (I) can be considered as being in a cisoid conformation, since the C31—N—S—C41 torsion angle is less than 90°. The bond lengths and angles in the pyrimidine and phenyl rings are in good agreement with the values observed for such rings in free sulfadiazine and the metal-sulfadiazinate complexes studied to date.