[4-Amino-N-(pyrimidin-2-yl)­benzene­sulfon­amido-κN](tri­phenyl­arsine-κAs)­gold(I)

The title compound, [Au(C₁₀H₉N₄O₂S)(C₁₈H₁₅As)], is isostructural with the tri­phenyl­phosphine analog [Lang et al. (2003). Acta Cryst. C59, m95–m96]. The geometry is nearly linear at the Au^I center, with Au—N = 2.0552 (15) Å, Au—As = 2.3266 (6) Å and N—Au—As = 171.56 (4)°. The mol­ecules are joined by intermolecular N—H...O bonds between the amine and sulfonyl groups of the sulfadiazine ligand. The slightly shorter Au—N distance in the title compound compared to its tri­phenyl­phosphine analog is due to packing effects.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.018
• wR factor = 0.043
• Data-to-parameter ratio = 28.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT028_ALERT_3_B _diffrn_measured_fraction_theta_max  Low .....       0.96

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.632     1.000
            Tmin and Tmax expected:      0.200     0.350
            RR =      1.107
            Please check that your absorption correction is appropriate.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ...................       0.35
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3A               ?

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.350
            Tmax scaled      0.350 Tmin scaled      0.221

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Recently, we reported the preparation and structural characterization of [4-amino-N-(pyrimidin-2-yl)benzenesulfonamido-κN](tripheylphosphine- κP)gold(I), also known as (sulfadiazinato)(triphenylphosphine)gold(I) (Lang et al., 2003). In this paper, we report the isostructural title compound, (I), also called (sulfadizinato)(triphenylarsine)gold(I). Compound (I) was obtained by the reaction of chloro(triphenylarsine)gold(I), sulfadiazine and triethylamine in methanol; recrystallization from dichloromethane and petroleum ether afforded single crystals. The asymmetric unit contains a complete molecule (Fig. 1) of the compound. Select bond distances and angles are given in Table 1.

Compound (I) is almost identical to its triphenylphosphine isostructual counterpart. The Au atom shows weak interactions with atoms O1 and N16 of the sulfadiazinate ligand [distances 2.9926 (13) and 3.0863 (17) Å respectively]. The sulfadiazinate N atom bonded to Au shows trigonal planar geometry; the sum of the angles about atom N1 is 360.4 (5)° The sulfonamide group is approximately tetrahedral. The two ring systems in the sulfadiazinate ligand of (I) can be considered as being in a cisoid conformation, since the C1—S—N1—C11 torsion angle is approximately 90°. Atom O2 of the sulfonamide group participates in intermolecular hydrogen bonding to the amino group of a neighbouring molecule to form continuous chains along the c axis (Table 2 and Fig. 2).

The compound (I) has a slightly shorter N—Au distance than that seen in (sulfadiazinato)(triphenylphosphine)gold(I), which has a N—Au distance of 2.0707 (18) Å. As the triphenylarsine ligand is slightly more Lewis basic relative to triphenylphosphine ligand (Aroney et al., 1994), the trans influence predicts a longer Au—N bond length for the former compared to the latter (Jones & Williams, 1977). The shorter distance in this case is likely caused by the packing forces due to the slightly larger triphenylarsine ligand. This is also shown by the closer intermolecular hydrogen bond interaction between an H atom of the amine group and an O atom of the nitro group in the sufadiazinate ligand in (I). The H···O distance is 0.103 Å shorter in (I) than in the triphenylphosphine analog. The bond distances within the sulfadiazinate ligands of the two complexes are equivalent.

S2. Experimental

To a solution of chloro(tripenylarsine)gold(I) (0.1 mmol) in methanol (5 ml), a solution of sulfadiazine (0.1 mmol) in methanol (5 ml) and triethylamine (0.1 mmol) were added. The resulting mixture was stirred under reflux for 2 h and them cooled to room temperature, after which the precipitated solid was separated by filtration (yield 80%, based on sulfadiazine). Recrystallization from dichloromethane and petroleum ether (1:1 v/v) afforded crystals of the pure product (I), after two weeks. Elemental Analysis (calculated/found): C 44.69/43.75, H 3.21/3.22, N 7.45/7.16%.

S3. Refinement

All H atoms were placed in calculated positions with C—H distances of 0.95 Å and N—H distances of 0.88 Å. They were included in the refinement in riding-motion approximation, with U_iso = 1.2U_eq of the carrier atom. The largest peak in the final difference Fourier map was located 0.75 Å from the Au atom.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 2000); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. A view of molecule of the molecule of (I) with the atomic labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of (I), showing the hydrogen bonding with dashed lines. Colour codes: gold Au, pink As, yellow S, red O, blue N, black C and grey H.

triphenylarsine sulfadiazine gold(I)

Crystal data

[Au(C10H9N4O2S)(C18H15As)]	F(000) = 1456
Mr = 752.46	Dx = 1.911 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1705 reflections
a = 12.0550 (18) Å	θ = 2.7–26.9°
b = 13.360 (2) Å	µ = 6.99 mm^−1
c = 16.774 (3) Å	T = 173 K
β = 104.46 (3)°	Block, colorless
V = 2616.0 (8) Å^3	0.30 × 0.20 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	8101 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ϕ and ω scans	θmax = 33.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→17
Tmin = 0.221, Tmax = 0.350	k = −20→20
35747 measured reflections	l = −23→25
9482 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.043	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0236P)^2] where P = (Fo^2 + 2Fc^2)/3
9482 reflections	(Δ/σ)max = 0.004
334 parameters	Δρmax = 1.03 e Å^−3
0 restraints	Δρmin = −0.59 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Au	0.337416 (5)	0.340050 (5)	0.807518 (4)	0.01926 (2)
S	0.07242 (4)	0.31367 (3)	0.77646 (3)	0.02052 (8)
As	0.479100 (14)	0.433631 (13)	0.770011 (10)	0.01763 (4)
O2	−0.01256 (11)	0.29864 (11)	0.82241 (8)	0.0293 (3)
N1	0.19560 (12)	0.26847 (11)	0.82703 (9)	0.0210 (3)
O1	0.09607 (12)	0.41508 (9)	0.75709 (8)	0.0281 (3)
C2	−0.01794 (15)	0.15342 (13)	0.67994 (11)	0.0220 (3)
H2	−0.0251	0.1218	0.7292	0.026*
C4	−0.04666 (15)	0.15075 (13)	0.53152 (11)	0.0211 (3)
C21	0.59015 (14)	0.49703 (13)	0.85810 (11)	0.0207 (3)
N16	0.31026 (15)	0.17054 (12)	0.92621 (11)	0.0304 (4)
C43	0.25141 (18)	0.65976 (14)	0.66225 (13)	0.0307 (4)
H43	0.1782	0.6824	0.6659	0.037*
C31	0.56449 (16)	0.36201 (13)	0.70579 (11)	0.0213 (3)
C41	0.40870 (14)	0.54386 (12)	0.70156 (10)	0.0197 (3)
C46	0.46496 (16)	0.59301 (14)	0.65025 (11)	0.0239 (4)
H46	0.5377	0.5701	0.6457	0.029*
C6	0.03713 (15)	0.29593 (13)	0.60984 (11)	0.0222 (3)
H6	0.0694	0.3610	0.6118	0.027*
C11	0.20566 (16)	0.18337 (13)	0.87590 (11)	0.0218 (3)
N12	0.11556 (15)	0.12289 (13)	0.86924 (11)	0.0336 (4)
C45	0.41475 (18)	0.67567 (14)	0.60561 (13)	0.0290 (4)
H45	0.4531	0.7094	0.5704	0.035*
C23	0.67389 (17)	0.51606 (16)	1.00306 (12)	0.0299 (4)
H23	0.6790	0.4961	1.0582	0.036*
C25	0.73574 (17)	0.62156 (15)	0.90710 (14)	0.0323 (4)
H25	0.7837	0.6736	0.8963	0.039*
C33	0.7332 (2)	0.32307 (19)	0.66034 (16)	0.0427 (6)
H33	0.8116	0.3348	0.6626	0.051*
C1	0.02853 (14)	0.24915 (13)	0.68281 (10)	0.0193 (3)
C5	−0.00087 (15)	0.24808 (14)	0.53535 (11)	0.0234 (3)
H5	0.0038	0.2810	0.4861	0.028*
C3	−0.05363 (15)	0.10442 (14)	0.60537 (11)	0.0227 (3)
H3	−0.0833	0.0384	0.6040	0.027*
C22	0.59805 (15)	0.46807 (14)	0.93877 (11)	0.0235 (3)
H22	0.5513	0.4152	0.9499	0.028*
C26	0.65931 (16)	0.57435 (14)	0.84223 (12)	0.0267 (4)
H26	0.6542	0.5947	0.7872	0.032*
C34	0.6751 (2)	0.25121 (18)	0.60904 (14)	0.0412 (5)
H34	0.7130	0.2131	0.5760	0.049*
C15	0.3221 (2)	0.09159 (17)	0.97625 (14)	0.0385 (5)
H15	0.3950	0.0796	1.0127	0.046*
N3	−0.08415 (16)	0.10332 (13)	0.45775 (10)	0.0315 (4)
H3A	−0.1133	0.0427	0.4558	0.038*
H3B	−0.0792	0.1333	0.4121	0.038*
C32	0.67941 (17)	0.37986 (19)	0.70983 (14)	0.0349 (5)
H32	0.7206	0.4298	0.7456	0.042*
C42	0.30106 (16)	0.57658 (14)	0.70741 (12)	0.0258 (4)
H42	0.2620	0.5424	0.7419	0.031*
C24	0.74211 (17)	0.59285 (15)	0.98731 (13)	0.0312 (4)
H24	0.7935	0.6260	1.0316	0.037*
C44	0.30843 (18)	0.70929 (15)	0.61223 (13)	0.0313 (4)
H44	0.2748	0.7666	0.5822	0.038*
C13	0.1322 (2)	0.04505 (17)	0.92152 (16)	0.0441 (6)
H13	0.0702	0.0005	0.9195	0.053*
C36	0.50640 (19)	0.28897 (16)	0.65317 (13)	0.0340 (5)
H36	0.4278	0.2767	0.6500	0.041*
C35	0.5618 (2)	0.23378 (18)	0.60514 (15)	0.0453 (6)
H35	0.5213	0.1836	0.5693	0.054*
C14	0.2341 (2)	0.02663 (18)	0.97773 (15)	0.0449 (6)
H14	0.2434	−0.0277	1.0154	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au	0.01641 (3)	0.02138 (3)	0.02015 (3)	−0.00411 (2)	0.00486 (2)	−0.00044 (2)
S	0.01774 (18)	0.02129 (19)	0.0234 (2)	−0.00154 (15)	0.00670 (16)	−0.00359 (16)
As	0.01466 (7)	0.01959 (8)	0.01850 (8)	−0.00208 (6)	0.00387 (6)	0.00051 (6)
O2	0.0230 (6)	0.0386 (8)	0.0297 (7)	−0.0041 (6)	0.0132 (6)	−0.0092 (6)
N1	0.0178 (7)	0.0227 (7)	0.0222 (7)	−0.0040 (5)	0.0042 (6)	0.0007 (6)
O1	0.0294 (7)	0.0176 (6)	0.0356 (8)	0.0000 (5)	0.0049 (6)	−0.0029 (5)
C2	0.0217 (8)	0.0246 (8)	0.0204 (8)	−0.0018 (7)	0.0063 (7)	0.0010 (7)
C4	0.0194 (8)	0.0253 (8)	0.0192 (8)	0.0025 (6)	0.0058 (6)	0.0006 (6)
C21	0.0166 (7)	0.0220 (8)	0.0221 (8)	−0.0008 (6)	0.0027 (6)	−0.0002 (6)
N16	0.0251 (8)	0.0326 (9)	0.0321 (9)	0.0003 (7)	0.0049 (7)	0.0061 (7)
C43	0.0280 (10)	0.0292 (10)	0.0337 (11)	0.0086 (8)	0.0055 (8)	−0.0019 (8)
C31	0.0216 (8)	0.0212 (8)	0.0220 (8)	0.0032 (6)	0.0073 (7)	0.0044 (6)
C41	0.0192 (8)	0.0195 (8)	0.0189 (8)	−0.0002 (6)	0.0021 (6)	−0.0025 (6)
C46	0.0211 (8)	0.0276 (9)	0.0219 (8)	−0.0013 (7)	0.0033 (7)	0.0021 (7)
C6	0.0207 (8)	0.0191 (8)	0.0277 (9)	0.0021 (6)	0.0079 (7)	0.0018 (7)
C11	0.0238 (8)	0.0219 (8)	0.0207 (8)	−0.0036 (6)	0.0075 (7)	−0.0012 (6)
N12	0.0317 (9)	0.0288 (8)	0.0380 (10)	−0.0120 (7)	0.0045 (8)	0.0058 (7)
C45	0.0308 (10)	0.0254 (9)	0.0287 (10)	−0.0036 (7)	0.0035 (8)	0.0042 (7)
C23	0.0284 (9)	0.0391 (11)	0.0210 (9)	0.0060 (8)	0.0038 (7)	−0.0043 (8)
C25	0.0247 (9)	0.0255 (9)	0.0420 (12)	−0.0055 (8)	−0.0008 (8)	−0.0015 (9)
C33	0.0276 (11)	0.0615 (16)	0.0426 (13)	0.0165 (10)	0.0157 (10)	0.0089 (11)
C1	0.0161 (7)	0.0218 (8)	0.0200 (8)	0.0018 (6)	0.0047 (6)	−0.0006 (6)
C5	0.0240 (8)	0.0253 (8)	0.0218 (8)	0.0038 (7)	0.0072 (7)	0.0051 (7)
C3	0.0237 (8)	0.0221 (8)	0.0220 (8)	−0.0036 (7)	0.0054 (7)	0.0013 (7)
C22	0.0222 (8)	0.0266 (9)	0.0221 (9)	0.0004 (7)	0.0061 (7)	−0.0009 (7)
C26	0.0221 (8)	0.0283 (9)	0.0273 (9)	−0.0060 (7)	0.0014 (7)	0.0040 (7)
C34	0.0555 (15)	0.0407 (12)	0.0339 (12)	0.0200 (11)	0.0234 (11)	0.0057 (10)
C15	0.0389 (12)	0.0369 (11)	0.0372 (12)	0.0055 (9)	0.0045 (9)	0.0102 (9)
N3	0.0463 (10)	0.0295 (8)	0.0190 (8)	−0.0092 (7)	0.0089 (7)	−0.0013 (6)
C32	0.0204 (9)	0.0487 (13)	0.0364 (11)	0.0025 (9)	0.0085 (8)	−0.0026 (10)
C42	0.0228 (9)	0.0288 (9)	0.0270 (9)	0.0025 (7)	0.0082 (7)	−0.0006 (7)
C24	0.0248 (9)	0.0304 (10)	0.0324 (10)	0.0035 (8)	−0.0040 (8)	−0.0111 (8)
C44	0.0355 (11)	0.0222 (9)	0.0322 (10)	0.0042 (8)	0.0012 (8)	0.0013 (8)
C13	0.0488 (14)	0.0307 (11)	0.0532 (15)	−0.0120 (10)	0.0139 (12)	0.0097 (10)
C36	0.0372 (11)	0.0317 (10)	0.0375 (12)	−0.0063 (9)	0.0176 (9)	−0.0099 (9)
C35	0.0628 (16)	0.0374 (12)	0.0435 (13)	−0.0036 (11)	0.0280 (12)	−0.0117 (10)
C14	0.0554 (15)	0.0335 (11)	0.0457 (14)	0.0031 (11)	0.0127 (12)	0.0166 (10)

Geometric parameters (Å, º)

Au—N1	2.0552 (15)	C6—H6	0.9500
Au—As	2.3266 (6)	C11—N12	1.336 (2)
Au—N16	3.0863 (19)	N12—C13	1.343 (3)
Au—O1	2.9926 (16)	C45—C44	1.388 (3)
Au—O2	4.3238 (15)	C45—H45	0.9500
S—O1	1.4384 (13)	C23—C24	1.381 (3)
S—O2	1.4417 (14)	C23—C22	1.385 (3)
S—N1	1.6309 (16)	C23—H23	0.9500
S—C1	1.7538 (18)	C25—C24	1.383 (3)
As—C31	1.9209 (19)	C25—C26	1.389 (3)
As—C21	1.9248 (19)	C25—H25	0.9500
As—C41	1.9288 (18)	C33—C34	1.361 (4)
N1—C11	1.389 (2)	C33—C32	1.398 (3)
C2—C3	1.382 (3)	C33—H33	0.9500
C2—C1	1.392 (2)	C5—H5	0.9500
C2—H2	0.9500	C3—H3	0.9500
C4—N3	1.363 (2)	C22—H22	0.9500
C4—C3	1.406 (2)	C26—H26	0.9500
C4—C5	1.408 (2)	C34—C35	1.371 (4)
C21—C22	1.388 (3)	C34—H34	0.9500
C21—C26	1.394 (2)	C15—C14	1.376 (3)
N16—C15	1.333 (3)	C15—H15	0.9500
N16—C11	1.342 (2)	N3—H3A	0.8800
C43—C44	1.379 (3)	N3—H3B	0.8800
C43—C42	1.393 (3)	C32—H32	0.9500
C43—H43	0.9500	C42—H42	0.9500
C31—C36	1.383 (3)	C24—H24	0.9500
C31—C32	1.391 (3)	C44—H44	0.9500
C41—C46	1.387 (3)	C13—C14	1.371 (4)
C41—C42	1.396 (2)	C13—H13	0.9500
C46—C45	1.386 (3)	C36—C35	1.381 (3)
C46—H46	0.9500	C36—H36	0.9500
C6—C5	1.376 (3)	C35—H35	0.9500
C6—C1	1.401 (2)	C14—H14	0.9500
N1—Au—As	171.56 (4)	C44—C45—H45	119.9
N1—Au—O1	54.00 (5)	C24—C23—C22	120.26 (19)
As—Au—O1	118.11 (3)	C24—C23—H23	119.9
N1—Au—N16	47.88 (6)	C22—C23—H23	119.9
As—Au—N16	140.54 (4)	C24—C25—C26	120.07 (19)
O1—Au—N16	100.13 (5)	C24—C25—H25	120.0
N1—Au—O2	21.37 (5)	C26—C25—H25	120.0
As—Au—O2	151.31 (2)	C34—C33—C32	121.1 (2)
O1—Au—O2	33.43 (3)	C34—C33—H33	119.4
N16—Au—O2	66.83 (5)	C32—C33—H33	119.4
O1—S—O2	117.35 (9)	C2—C1—C6	119.77 (16)
O1—S—N1	105.08 (8)	C2—C1—S	120.74 (14)
O2—S—N1	110.28 (8)	C6—C1—S	119.45 (13)
O1—S—C1	107.04 (9)	C6—C5—C4	120.55 (17)
O2—S—C1	108.35 (8)	C6—C5—H5	119.7
N1—S—C1	108.41 (8)	C4—C5—H5	119.7
C31—As—C21	106.40 (8)	C2—C3—C4	121.02 (17)
C31—As—C41	105.32 (8)	C2—C3—H3	119.5
C21—As—C41	103.84 (8)	C4—C3—H3	119.5
C31—As—Au	114.61 (6)	C23—C22—C21	120.10 (18)
C21—As—Au	116.46 (6)	C23—C22—H22	120.0
C41—As—Au	109.13 (6)	C21—C22—H22	120.0
C11—N1—S	122.95 (12)	C25—C26—C21	119.87 (18)
C11—N1—Au	121.43 (12)	C25—C26—H26	120.1
S—N1—Au	115.49 (8)	C21—C26—H26	120.1
S—O1—Au	81.62 (6)	C33—C34—C35	120.0 (2)
C3—C2—C1	119.87 (17)	C33—C34—H34	120.0
C3—C2—H2	120.1	C35—C34—H34	120.0
C1—C2—H2	120.1	N16—C15—C14	123.2 (2)
N3—C4—C3	121.07 (16)	N16—C15—H15	118.4
N3—C4—C5	120.54 (17)	C14—C15—H15	118.4
C3—C4—C5	118.39 (17)	C4—N3—H3A	120.0
C22—C21—C26	119.62 (17)	C4—N3—H3B	120.0
C22—C21—As	119.41 (13)	H3A—N3—H3B	120.0
C26—C21—As	120.92 (14)	C31—C32—C33	118.8 (2)
C15—N16—C11	115.69 (18)	C31—C32—H32	120.6
C15—N16—Au	167.06 (15)	C33—C32—H32	120.6
C11—N16—Au	74.63 (11)	C43—C42—C41	119.49 (18)
C44—C43—C42	120.12 (19)	C43—C42—H42	120.3
C44—C43—H43	119.9	C41—C42—H42	120.3
C42—C43—H43	119.9	C23—C24—C25	120.08 (18)
C36—C31—C32	119.44 (19)	C23—C24—H24	120.0
C36—C31—As	116.91 (14)	C25—C24—H24	120.0
C32—C31—As	123.65 (15)	C43—C44—C45	120.24 (18)
C46—C41—C42	120.18 (17)	C43—C44—H44	119.9
C46—C41—As	121.35 (13)	C45—C44—H44	119.9
C42—C41—As	118.41 (14)	N12—C13—C14	123.4 (2)
C45—C46—C41	119.83 (18)	N12—C13—H13	118.3
C45—C46—H46	120.1	C14—C13—H13	118.3
C41—C46—H46	120.1	C35—C36—C31	120.5 (2)
C5—C6—C1	120.36 (17)	C35—C36—H36	119.7
C5—C6—H6	119.8	C31—C36—H36	119.7
C1—C6—H6	119.8	C34—C35—C36	120.2 (2)
N12—C11—N16	126.31 (18)	C34—C35—H35	119.9
N12—C11—N1	119.77 (17)	C36—C35—H35	119.9
N16—C11—N1	113.92 (16)	C13—C14—C15	115.9 (2)
C11—N12—C13	115.36 (19)	C13—C14—H14	122.0
C46—C45—C44	120.13 (19)	C15—C14—H14	122.0
C46—C45—H45	119.9
C1—S—N1—C11	−84.01 (16)	C31—As—C41—C42	146.53 (14)
O1—Au—As—C31	−122.55 (7)	C21—As—C41—C42	−101.82 (15)
N16—Au—As—C31	73.18 (8)	Au—As—C41—C42	23.02 (15)
O2—Au—As—C31	−128.33 (7)	C42—C41—C46—C45	0.9 (3)
O1—Au—As—C21	112.35 (7)	As—C41—C46—C45	−176.14 (14)
N16—Au—As—C21	−51.92 (8)	C15—N16—C11—N12	−3.0 (3)
O2—Au—As—C21	106.57 (7)	Au—N16—C11—N12	168.7 (2)
O1—Au—As—C41	−4.75 (6)	C15—N16—C11—N1	177.66 (17)
N16—Au—As—C41	−169.02 (7)	Au—N16—C11—N1	−10.70 (13)
O2—Au—As—C41	−10.53 (7)	S—N1—C11—N12	14.5 (2)
O1—S—O2—Au	−92.82 (11)	Au—N1—C11—N12	−161.05 (14)
N1—S—O2—Au	27.40 (8)	S—N1—C11—N16	−166.06 (14)
C1—S—O2—Au	145.90 (12)	Au—N1—C11—N16	18.4 (2)
N1—Au—O2—S	−109.95 (16)	N16—C11—N12—C13	3.5 (3)
As—Au—O2—S	60.00 (12)	N1—C11—N12—C13	−177.19 (19)
O1—Au—O2—S	50.72 (10)	C41—C46—C45—C44	0.0 (3)
N16—Au—O2—S	−134.69 (11)	C3—C2—C1—C6	1.0 (3)
O1—S—N1—C11	161.81 (14)	C3—C2—C1—S	179.02 (14)
O2—S—N1—C11	34.46 (17)	C5—C6—C1—C2	0.5 (3)
O1—S—N1—Au	−22.37 (11)	C5—C6—C1—S	−177.52 (13)
O2—S—N1—Au	−149.73 (8)	O1—S—C1—C2	−169.68 (14)
C1—S—N1—Au	91.80 (10)	O2—S—C1—C2	−42.25 (17)
O1—Au—N1—C11	−171.50 (16)	N1—S—C1—C2	77.44 (16)
N16—Au—N1—C11	−9.72 (12)	O1—S—C1—C6	8.31 (16)
O2—Au—N1—C11	−158.5 (2)	O2—S—C1—C6	135.74 (14)
O1—Au—N1—S	12.61 (6)	N1—S—C1—C6	−104.57 (15)
N16—Au—N1—S	174.40 (12)	C1—C6—C5—C4	−1.3 (3)
O2—Au—N1—S	25.63 (7)	N3—C4—C5—C6	−179.91 (17)
O2—S—O1—Au	136.72 (7)	C3—C4—C5—C6	0.7 (3)
N1—S—O1—Au	13.80 (7)	C1—C2—C3—C4	−1.7 (3)
C1—S—O1—Au	−101.33 (7)	N3—C4—C3—C2	−178.56 (18)
N1—Au—O1—S	−13.06 (6)	C5—C4—C3—C2	0.9 (3)
As—Au—O1—S	163.40 (4)	C24—C23—C22—C21	−0.1 (3)
N16—Au—O1—S	−26.68 (7)	C26—C21—C22—C23	0.3 (3)
O2—Au—O1—S	−21.63 (4)	As—C21—C22—C23	−177.09 (14)
C31—As—C21—C22	−115.03 (15)	C24—C25—C26—C21	−0.9 (3)
C41—As—C21—C22	134.11 (14)	C22—C21—C26—C25	0.2 (3)
Au—As—C21—C22	14.13 (16)	As—C21—C26—C25	177.52 (15)
C31—As—C21—C26	67.66 (16)	C32—C33—C34—C35	0.2 (4)
C41—As—C21—C26	−43.21 (17)	C11—N16—C15—C14	−0.3 (3)
Au—As—C21—C26	−163.19 (13)	Au—N16—C15—C14	−141.6 (6)
N1—Au—N16—C15	153.1 (7)	C36—C31—C32—C33	0.0 (3)
As—Au—N16—C15	−26.1 (7)	As—C31—C32—C33	179.88 (17)
O1—Au—N16—C15	168.0 (7)	C34—C33—C32—C31	−0.2 (4)
O2—Au—N16—C15	165.0 (7)	C44—C43—C42—C41	0.0 (3)
N1—Au—N16—C11	8.90 (11)	C46—C41—C42—C43	−0.9 (3)
As—Au—N16—C11	−170.28 (9)	As—C41—C42—C43	176.23 (14)
O1—Au—N16—C11	23.78 (11)	C22—C23—C24—C25	−0.6 (3)
O2—Au—N16—C11	20.76 (10)	C26—C25—C24—C23	1.1 (3)
C21—As—C31—C36	162.71 (15)	C42—C43—C44—C45	1.0 (3)
C41—As—C31—C36	−87.46 (16)	C46—C45—C44—C43	−1.0 (3)
Au—As—C31—C36	32.48 (17)	C11—N12—C13—C14	−0.7 (4)
C21—As—C31—C32	−17.22 (19)	C32—C31—C36—C35	0.2 (3)
C41—As—C31—C32	92.61 (18)	As—C31—C36—C35	−179.70 (18)
Au—As—C31—C32	−147.45 (16)	C33—C34—C35—C36	0.0 (4)
C31—As—C41—C46	−36.37 (16)	C31—C36—C35—C34	−0.2 (4)
C21—As—C41—C46	75.29 (15)	N12—C13—C14—C15	−2.1 (4)
Au—As—C41—C46	−159.87 (13)	N16—C15—C14—C13	2.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O2^i	0.88	2.08	2.931 (2)	162

Symmetry code: (i) x, −y+1/2, z−1/2.