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The title compound, [Au(C10H9N4O2S)(C18H15P)], is nearly linear at AuI, with Au—N = 2.0707 (18) Å, Au—P = 2.2310 (8) Å and N—Au—P 171.93 (5)°. The mol­ecules are linked by intermolecular N—H...O bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103001914/na1589sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103001914/na1589Isup2.hkl
Contains datablock I

CCDC reference: 207998

Comment top

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.

Experimental top

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%.

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] 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.
[4-Amino-N-(pyrimidin-2-yl)benzenesulfonamido-κN](triphenylphosphine- κP)gold(I) top
Crystal data top
[Au(C10H9N4O2S)(C18H15P)]F(000) = 1384
Mr = 708.51Dx = 1.838 Mg m3
Monoclinic, P21/cMelting point: 0 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71069 Å
a = 11.878 (5) ÅCell parameters from 7802 reflections
b = 13.329 (5) Åθ = 1.8–30.8°
c = 16.677 (5) ŵ = 5.92 mm1
β = 104.085 (5)°T = 293 K
V = 2561.0 (16) Å3Block, colourless
Z = 40.25 × 0.19 × 0.13 mm
Data collection top
Bruker Model CCD area-detector
diffractometer
6618 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 30.6°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.288, Tmax = 0.463k = 1919
31145 measured reflectionsl = 2323
7802 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.045H 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 parametersΔρmax = 1.15 e Å3
0 restraintsΔρmin = 0.54 e Å3
Crystal data top
[Au(C10H9N4O2S)(C18H15P)]V = 2561.0 (16) Å3
Mr = 708.51Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.878 (5) ŵ = 5.92 mm1
b = 13.329 (5) ÅT = 293 K
c = 16.677 (5) Å0.25 × 0.19 × 0.13 mm
β = 104.085 (5)°
Data collection top
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 = 0.463Rint = 0.029
31145 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0190 restraints
wR(F2) = 0.045H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 1.15 e Å3
7802 reflectionsΔρmin = 0.54 e Å3
342 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
xyzUiso*/Ueq
Au0.656917 (7)0.155522 (6)0.194110 (5)0.01488 (3)
P0.51967 (5)0.06351 (4)0.22946 (3)0.01384 (10)
C10.41685 (18)0.00460 (15)0.14428 (13)0.0158 (4)
C20.40778 (18)0.03882 (16)0.06376 (13)0.0181 (4)
H20.45250.09290.05460.022*
C30.33209 (19)0.00766 (18)0.00270 (13)0.0226 (5)
H30.32660.01510.05620.027*
C40.2650 (2)0.08779 (18)0.01085 (15)0.0251 (5)
H40.21510.11920.03370.03*
C50.2716 (2)0.12147 (18)0.09039 (15)0.0261 (5)
H50.22510.17440.09930.031*
C60.34796 (19)0.07594 (17)0.15684 (14)0.0220 (5)
H60.35320.09930.21020.026*
C110.43587 (19)0.13134 (16)0.28905 (13)0.0171 (4)
C120.4929 (2)0.20560 (18)0.34218 (14)0.0241 (5)
H120.57060.21910.34480.029*
C130.4360 (3)0.2598 (2)0.39120 (16)0.0327 (6)
H130.47530.30920.42660.039*
C140.3213 (2)0.2404 (2)0.38746 (15)0.0327 (6)
H140.2830.27660.42050.039*
C150.2629 (2)0.1676 (2)0.33508 (16)0.0330 (6)
H150.18530.15460.33310.04*
C160.3189 (2)0.1130 (2)0.28489 (15)0.0263 (5)
H160.27860.06470.24890.032*
C210.58780 (17)0.03976 (15)0.29467 (12)0.0152 (4)
C220.69602 (19)0.07500 (16)0.28732 (13)0.0188 (4)
H220.7340.04280.2520.023*
C230.7468 (2)0.15789 (17)0.33256 (14)0.0228 (5)
H230.81850.18110.32750.027*
C240.6898 (2)0.20615 (16)0.38562 (14)0.0217 (5)
H240.72330.26210.41540.026*
C250.5832 (2)0.17082 (16)0.39405 (14)0.0213 (5)
H250.54580.20280.42990.026*
C260.53242 (19)0.08785 (16)0.34909 (13)0.0180 (4)
H260.46130.06420.35520.022*
N0.80060 (15)0.23046 (13)0.17456 (11)0.0173 (4)
C310.79122 (19)0.31454 (16)0.12459 (13)0.0178 (4)
N320.88187 (18)0.37703 (16)0.13279 (13)0.0268 (4)
C330.8673 (2)0.45374 (19)0.07949 (17)0.0343 (6)
H330.92890.49780.08240.041*
C340.7660 (2)0.4706 (2)0.02083 (17)0.0344 (6)
H340.75810.52360.01640.041*
C350.6764 (2)0.40417 (19)0.02042 (15)0.0283 (5)
H350.60550.41460.01730.034*
N360.68677 (17)0.32592 (14)0.07146 (12)0.0227 (4)
S0.92547 (5)0.18562 (4)0.22536 (3)0.01684 (10)
O11.01158 (14)0.20031 (13)0.17878 (10)0.0231 (3)
O20.90231 (14)0.08390 (11)0.24586 (10)0.0225 (3)
C410.96986 (18)0.25159 (16)0.31911 (13)0.0169 (4)
C420.96067 (18)0.20450 (17)0.39281 (13)0.0183 (4)
H420.92840.14080.39120.022*
C430.99970 (19)0.25319 (17)0.46733 (14)0.0207 (4)
H430.99430.22150.51590.025*
C441.04781 (19)0.35057 (16)0.47091 (13)0.0186 (4)
C451.05386 (19)0.39625 (17)0.39597 (13)0.0204 (4)
H451.08340.4610.39680.025*
C461.01685 (19)0.34703 (17)0.32103 (14)0.0201 (4)
H461.02350.37780.27230.024*
N441.0867 (2)0.39766 (17)0.54478 (13)0.0284 (5)
H44A1.070 (3)0.375 (2)0.5933 (19)0.040 (8)*
H44B1.110 (3)0.460 (2)0.5454 (17)0.036 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au0.01356 (4)0.01590 (4)0.01537 (4)0.00328 (3)0.00391 (3)0.00010 (3)
P0.0126 (2)0.0146 (2)0.0144 (2)0.00131 (19)0.00350 (19)0.00070 (19)
C10.0136 (9)0.0157 (9)0.0171 (9)0.0008 (7)0.0017 (8)0.0008 (7)
C20.0159 (10)0.0190 (10)0.0201 (10)0.0009 (8)0.0056 (8)0.0002 (8)
C30.0210 (11)0.0299 (12)0.0154 (10)0.0043 (9)0.0015 (8)0.0033 (9)
C40.0191 (11)0.0243 (12)0.0266 (12)0.0028 (9)0.0047 (9)0.0106 (9)
C50.0197 (11)0.0200 (11)0.0348 (13)0.0051 (9)0.0010 (10)0.0002 (10)
C60.0191 (11)0.0210 (11)0.0235 (11)0.0037 (9)0.0004 (9)0.0047 (9)
C110.0175 (10)0.0175 (10)0.0173 (10)0.0046 (8)0.0064 (8)0.0043 (8)
C120.0273 (12)0.0237 (12)0.0239 (11)0.0017 (9)0.0115 (10)0.0037 (9)
C130.0470 (16)0.0272 (13)0.0289 (13)0.0025 (12)0.0190 (12)0.0070 (10)
C140.0436 (16)0.0353 (14)0.0248 (12)0.0195 (12)0.0190 (11)0.0079 (11)
C150.0206 (12)0.0509 (17)0.0301 (13)0.0144 (11)0.0111 (10)0.0100 (12)
C160.0157 (11)0.0382 (14)0.0257 (12)0.0037 (10)0.0060 (9)0.0009 (10)
C210.0149 (9)0.0144 (9)0.0160 (9)0.0010 (8)0.0028 (7)0.0014 (7)
C220.0171 (10)0.0192 (10)0.0211 (10)0.0013 (8)0.0065 (8)0.0004 (8)
C230.0215 (11)0.0208 (11)0.0254 (11)0.0055 (9)0.0044 (9)0.0040 (9)
C240.0251 (12)0.0147 (10)0.0236 (11)0.0021 (9)0.0025 (9)0.0001 (8)
C250.0251 (12)0.0181 (11)0.0201 (10)0.0029 (9)0.0042 (9)0.0051 (8)
C260.0153 (10)0.0196 (10)0.0186 (10)0.0012 (8)0.0032 (8)0.0015 (8)
N0.0149 (8)0.0202 (9)0.0164 (8)0.0032 (7)0.0030 (7)0.0024 (7)
C310.0197 (10)0.0182 (10)0.0168 (10)0.0023 (8)0.0067 (8)0.0016 (8)
N320.0248 (11)0.0234 (10)0.0311 (11)0.0078 (8)0.0049 (9)0.0035 (8)
C330.0331 (14)0.0270 (13)0.0433 (15)0.0075 (11)0.0102 (12)0.0075 (11)
C340.0435 (16)0.0252 (13)0.0347 (14)0.0021 (12)0.0100 (12)0.0123 (11)
C350.0265 (13)0.0290 (13)0.0272 (12)0.0030 (10)0.0025 (10)0.0057 (10)
N360.0213 (10)0.0232 (10)0.0232 (10)0.0001 (8)0.0049 (8)0.0033 (8)
S0.0144 (2)0.0177 (2)0.0189 (2)0.00074 (19)0.00485 (19)0.00249 (19)
O10.0186 (8)0.0297 (9)0.0235 (8)0.0018 (7)0.0099 (6)0.0059 (7)
O20.0227 (8)0.0164 (8)0.0272 (8)0.0007 (6)0.0038 (7)0.0012 (6)
C410.0132 (9)0.0192 (10)0.0185 (10)0.0013 (8)0.0040 (8)0.0018 (8)
C420.0157 (10)0.0188 (10)0.0207 (10)0.0023 (8)0.0048 (8)0.0007 (8)
C430.0194 (11)0.0242 (11)0.0187 (10)0.0032 (9)0.0048 (8)0.0022 (8)
C440.0177 (10)0.0213 (10)0.0176 (10)0.0024 (8)0.0059 (8)0.0005 (8)
C450.0208 (11)0.0197 (11)0.0211 (11)0.0023 (9)0.0056 (9)0.0019 (8)
C460.0176 (10)0.0227 (11)0.0205 (10)0.0003 (9)0.0059 (8)0.0010 (9)
N440.0374 (13)0.0276 (12)0.0211 (10)0.0067 (10)0.0090 (9)0.0017 (9)
Geometric parameters (Å, º) top
Au—N2.0707 (18)C23—H230.93
Au—P2.2310 (8)C24—C251.390 (3)
Au—O22.9880 (19)C24—H240.93
Au—N363.134 (2)C25—C261.389 (3)
P—C111.810 (2)C25—H250.93
P—C11.812 (2)C26—H260.93
P—C211.818 (2)N—C311.385 (3)
C1—C61.396 (3)N—S1.6320 (19)
C1—C21.397 (3)C31—N321.342 (3)
C2—C31.391 (3)C31—N361.346 (3)
C2—H20.93N32—C331.338 (3)
C3—C41.384 (3)C33—C341.372 (4)
C3—H30.93C33—H330.93
C4—C51.384 (3)C34—C351.384 (4)
C4—H40.93C34—H340.93
C5—C61.389 (3)C35—N361.333 (3)
C5—H50.93C35—H350.93
C6—H60.93S—O11.4405 (16)
C11—C121.390 (3)S—O21.4410 (17)
C11—C161.395 (3)S—C411.759 (2)
C12—C131.385 (3)C41—C461.386 (3)
C12—H120.93C41—C421.408 (3)
C13—C141.372 (4)C42—C431.378 (3)
C13—H130.93C42—H420.93
C14—C151.376 (4)C43—C441.413 (3)
C14—H140.93C43—H430.93
C15—C161.394 (3)C44—N441.359 (3)
C15—H150.93C44—C451.408 (3)
C16—H160.93C45—C461.385 (3)
C21—C261.399 (3)C45—H450.93
C21—C221.402 (3)C46—H460.93
C22—C231.390 (3)N44—H44A0.93 (3)
C22—H220.93N44—H44B0.88 (3)
C23—C241.395 (3)
N—Au—P171.93 (5)C25—C24—C23120.2 (2)
N—Au—O254.28 (6)C25—C24—H24119.9
P—Au—O2118.18 (4)C23—C24—H24119.9
N—Au—N3647.09 (6)C26—C25—C24120.1 (2)
P—Au—N36140.98 (4)C26—C25—H25119.9
O2—Au—N3699.36 (5)C24—C25—H25119.9
C11—P—C1106.93 (10)C25—C26—C21120.3 (2)
C11—P—C21105.90 (10)C25—C26—H26119.9
C1—P—C21104.95 (10)C21—C26—H26119.9
C11—P—Au113.91 (8)C31—N—S122.60 (15)
C1—P—Au115.31 (7)C31—N—Au122.44 (14)
C21—P—Au109.07 (7)S—N—Au114.92 (10)
C6—C1—C2119.0 (2)N32—C31—N36125.8 (2)
C6—C1—P121.56 (16)N32—C31—N119.7 (2)
C2—C1—P119.46 (16)N36—C31—N114.43 (19)
C3—C2—C1120.3 (2)C33—N32—C31115.8 (2)
C3—C2—H2119.9N32—C33—C34123.2 (2)
C1—C2—H2119.9N32—C33—H33118.4
C4—C3—C2120.0 (2)C34—C33—H33118.4
C4—C3—H3120C33—C34—C35116.0 (2)
C2—C3—H3120C33—C34—H34122
C3—C4—C5120.4 (2)C35—C34—H34122
C3—C4—H4119.8N36—C35—C34123.1 (2)
C5—C4—H4119.8N36—C35—H35118.4
C4—C5—C6119.8 (2)C34—C35—H35118.4
C4—C5—H5120.1C35—N36—C31115.8 (2)
C6—C5—H5120.1C35—N36—Au167.52 (16)
C5—C6—C1120.6 (2)C31—N36—Au73.82 (12)
C5—C6—H6119.7O1—S—O2117.22 (10)
C1—C6—H6119.7O1—S—N110.19 (10)
C12—C11—C16118.8 (2)O2—S—N105.42 (10)
C12—C11—P117.24 (17)O1—S—C41108.23 (10)
C16—C11—P123.98 (18)O2—S—C41107.02 (10)
C13—C12—C11121.0 (2)N—S—C41108.44 (10)
C13—C12—H12119.5S—O2—Au81.95 (7)
C11—C12—H12119.5C46—C41—C42120.3 (2)
C14—C13—C12119.8 (3)C46—C41—S120.74 (16)
C14—C13—H13120.1C42—C41—S118.88 (16)
C12—C13—H13120.1C43—C42—C41119.8 (2)
C13—C14—C15120.2 (2)C43—C42—H42120.1
C13—C14—H14119.9C41—C42—H42120.1
C15—C14—H14119.9C42—C43—C44120.9 (2)
C14—C15—C16120.6 (2)C42—C43—H43119.5
C14—C15—H15119.7C44—C43—H43119.5
C16—C15—H15119.7N44—C44—C45121.7 (2)
C15—C16—C11119.6 (2)N44—C44—C43120.4 (2)
C15—C16—H16120.2C45—C44—C43117.9 (2)
C11—C16—H16120.2C46—C45—C44121.5 (2)
C26—C21—C22119.3 (2)C46—C45—H45119.2
C26—C21—P121.59 (16)C44—C45—H45119.2
C22—C21—P119.06 (16)C45—C46—C41119.5 (2)
C23—C22—C21120.3 (2)C45—C46—H46120.2
C23—C22—H22119.8C41—C46—H46120.2
C21—C22—H22119.8C44—N44—H44A123 (2)
C22—C23—C24119.8 (2)C44—N44—H44B119.0 (19)
C22—C23—H23120.1H44A—N44—H44B115 (3)
C24—C23—H23120.1
C31—N—S—C4184.45 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N44—H44A···O1i0.93 (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)]
Mr708.51
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.878 (5), 13.329 (5), 16.677 (5)
β (°) 104.085 (5)
V3)2561.0 (16)
Z4
Radiation typeMo Kα
µ (mm1)5.92
Crystal size (mm)0.25 × 0.19 × 0.13
Data collection
DiffractometerBruker Model CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.288, 0.463
No. of measured, independent and
observed [I > 2σ(I)] reflections
31145, 7802, 6618
Rint0.029
(sin θ/λ)max1)0.715
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.019, 0.045, 1.02
No. of reflections7802
No. of parameters342
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.15, 0.54

Computer programs: Bruker software Please provide full details, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
Au—N2.0707 (18)N—S1.6320 (19)
Au—P2.2310 (8)S—O11.4405 (16)
Au—O22.9880 (19)S—O21.4410 (17)
Au—N363.134 (2)S—C411.759 (2)
N—Au—P171.93 (5)O1—S—O2117.22 (10)
N—Au—O254.28 (6)O1—S—N110.19 (10)
P—Au—O2118.18 (4)O2—S—N105.42 (10)
N—Au—N3647.09 (6)O1—S—C41108.23 (10)
P—Au—N36140.98 (4)O2—S—C41107.02 (10)
C31—N—S122.60 (15)N—S—C41108.44 (10)
C31—N—Au122.44 (14)S—O2—Au81.95 (7)
S—N—Au114.92 (10)
C31—N—S—C4184.45 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N44—H44A···O1i0.93 (3)2.00 (3)2.909 (3)165 (3)
Symmetry code: (i) x, y+1/2, z+1/2.
 

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