Synthesis, crystal structure and studies on the inter­action with albumin of a new silver(I) complex based on 2-(4-nitro­benzene­sulfonamido)­benzoic acid

In the present work, the two-dimensional (2D) polymer poly[[μ₄-2-(4-nitro­benzene­sulfonamido)­benzoato-κ⁴O¹:O¹:O^1′:N⁶]silver(I)] (AgL), [Ag(C₁₃H₉N₂O₆S)]_n, was obtained from 2-(4-nitro­benzene­sulfonamido)­benzoic acid (HL), C₁₃H₁₀N₂O₆S. FT–IR, ¹H and ¹³C{¹H} NMR spectroscopic analyses were used to characterize both compounds. The crystal structures of HL and AgL were determined by single-crystal X-ray diffraction. In the structure of HL, O—H...O hydrogen bonds between neighbouring mol­ecules result in the formation of dimers, while the silver(I) complex shows polymerization associated with the O atoms of three distinct deprotonated ligands (L⁻). Thus, the structure of the Ag complex can be considered as a coordination polymer consisting of a one-dimensional linear chain, constructed by carboxyl­ate bridging groups, running parallel to the b axis. Neighbouring polymeric chains are further bridged by Ag—C monohapto contacts, resulting in a 2D framework. Fingerprint analysis of the Hirshfeld surfaces show that O...H/H...O hydrogen bonds are responsible for the most significant contacts in the crystal packing of HL and AgL, followed by the H...H and O...C/C...O inter­actions. The Ag...Ag, Ag...O/O...Ag and Ag...C/C...Ag inter­actions in the Hirshfeld surface represent 12.1% of the total inter­actions in the crystal packing. Studies of the inter­actions of the compounds with human serum albumin (HSA) indicated that both HL and AgL inter­act with HSA.

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015).

2-(4-Nitrobenzenesulfonamido)benzoic acid (HL)

Crystal data

C13H10N2O6S	Z = 2
Mr = 322.29	F(000) = 332
Triclinic, P1	Dx = 1.617 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9140 (3) Å	Cell parameters from 5557 reflections
b = 10.0641 (5) Å	θ = 3.1–32.6°
c = 10.1532 (5) Å	µ = 0.28 mm^−1
α = 102.153 (4)°	T = 301 K
β = 100.951 (4)°	Prism, colourless
γ = 99.745 (4)°	0.68 × 0.35 × 0.14 mm
V = 661.77 (6) Å^3

Data collection

Rigaku Xcalibur, Atlas, Gemini ultra diffractometer	4515 independent reflections
Graphite monochromator	3841 reflections with I > 2σ(I)
Detector resolution: 10.4186 pixels mm^-1	Rint = 0.043
ω scans	θmax = 32.8°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	h = −10→10
Tmin = 0.901, Tmax = 1.000	k = −14→14
13718 measured reflections	l = −15→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.1382P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
4515 reflections	Δρmax = 0.33 e Å^−3
200 parameters	Δρmin = −0.37 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Single-crystal X-ray diffraction measurements were performed on an Agilent–Gemini diffractometer equipped with a CCD area detector using MoK? (0.71073 Å) radiation. The CrysAlisPro software package (Rigaku, 2015) was used for data collection and reduction (Oxford Diffraction Ltda, version 171.38.41). The structures were solved by direct methods using SHELXS-97 and refined by full-matrix least squares on F² using SHELXL-2018 (Sheldrick, 2015). All non-hydrogen atoms were refined using anisotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.12454 (4)	0.47628 (3)	0.74105 (3)	0.02885 (9)
O1	−0.33898 (16)	−0.03940 (10)	0.38167 (11)	0.0433 (2)
H1	−0.443606	−0.066604	0.404167	0.065*
O2	−0.32527 (14)	0.14767 (10)	0.54881 (12)	0.0406 (2)
O3	−0.01498 (16)	0.51483 (10)	0.82160 (11)	0.0403 (2)
O4	0.25416 (15)	0.58008 (10)	0.70247 (11)	0.0393 (2)
O5	0.58057 (18)	0.11306 (11)	1.12775 (11)	0.0458 (3)
O6	0.79937 (17)	0.14961 (13)	1.00541 (14)	0.0546 (3)
N1	−0.01504 (15)	0.36229 (11)	0.60268 (11)	0.0308 (2)
H1N	−0.129422	0.323849	0.611424	0.037*
N2	0.64156 (17)	0.16245 (12)	1.03919 (12)	0.0358 (2)
C1	−0.25207 (18)	0.08679 (13)	0.45781 (13)	0.0307 (2)
C2	−0.06143 (17)	0.14679 (12)	0.42646 (12)	0.0276 (2)
C3	0.05425 (17)	0.28066 (12)	0.49812 (12)	0.0265 (2)
C4	0.2329 (2)	0.33032 (15)	0.46234 (14)	0.0361 (3)
H4	0.30801	0.419659	0.507179	0.043*
C5	0.2993 (2)	0.24796 (17)	0.36091 (16)	0.0418 (3)
H5	0.420223	0.281618	0.33951	0.05*
C6	0.1880 (2)	0.11621 (16)	0.29097 (15)	0.0414 (3)
H6	0.233994	0.060917	0.223264	0.05*
C7	0.0083 (2)	0.06735 (14)	0.32238 (14)	0.0364 (3)
H7	−0.068407	−0.020376	0.273293	0.044*
C8	0.28090 (17)	0.38494 (12)	0.83002 (12)	0.0280 (2)
C9	0.2009 (2)	0.30539 (16)	0.91162 (16)	0.0380 (3)
H9	0.068394	0.301506	0.919686	0.046*
C10	0.3196 (2)	0.23221 (15)	0.98058 (15)	0.0373 (3)
H10	0.268501	0.178123	1.035203	0.045*
C11	0.51523 (19)	0.24128 (12)	0.96650 (13)	0.0300 (2)
C12	0.5970 (2)	0.32060 (15)	0.88735 (15)	0.0370 (3)
H12	0.72984	0.324516	0.880113	0.044*
C13	0.47850 (19)	0.39464 (15)	0.81850 (14)	0.0349 (3)
H13	0.53117	0.449933	0.765428	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02764 (15)	0.02435 (15)	0.03087 (16)	0.00152 (11)	0.00438 (11)	0.00453 (11)
O1	0.0386 (5)	0.0351 (5)	0.0449 (6)	−0.0104 (4)	0.0123 (4)	−0.0017 (4)
O2	0.0288 (4)	0.0346 (5)	0.0517 (6)	−0.0038 (4)	0.0147 (4)	0.0000 (4)
O3	0.0398 (5)	0.0385 (5)	0.0421 (5)	0.0128 (4)	0.0122 (4)	0.0032 (4)
O4	0.0375 (5)	0.0283 (4)	0.0465 (6)	−0.0046 (4)	0.0031 (4)	0.0126 (4)
O5	0.0538 (6)	0.0428 (6)	0.0410 (6)	0.0088 (5)	0.0051 (5)	0.0176 (5)
O6	0.0403 (6)	0.0572 (7)	0.0746 (9)	0.0202 (5)	0.0156 (6)	0.0252 (6)
N1	0.0230 (4)	0.0315 (5)	0.0319 (5)	−0.0014 (4)	0.0053 (4)	0.0022 (4)
N2	0.0355 (6)	0.0292 (5)	0.0378 (6)	0.0047 (4)	0.0019 (4)	0.0056 (4)
C1	0.0255 (5)	0.0294 (6)	0.0331 (6)	−0.0002 (4)	0.0031 (4)	0.0071 (5)
C2	0.0251 (5)	0.0295 (5)	0.0266 (5)	0.0017 (4)	0.0043 (4)	0.0081 (4)
C3	0.0245 (5)	0.0288 (5)	0.0248 (5)	0.0022 (4)	0.0032 (4)	0.0087 (4)
C4	0.0309 (6)	0.0377 (7)	0.0360 (6)	−0.0037 (5)	0.0097 (5)	0.0086 (5)
C5	0.0376 (7)	0.0519 (8)	0.0392 (7)	0.0040 (6)	0.0172 (6)	0.0160 (6)
C6	0.0457 (8)	0.0464 (8)	0.0355 (7)	0.0098 (6)	0.0192 (6)	0.0092 (6)
C7	0.0414 (7)	0.0345 (6)	0.0303 (6)	0.0035 (5)	0.0095 (5)	0.0041 (5)
C8	0.0261 (5)	0.0274 (5)	0.0277 (5)	0.0018 (4)	0.0051 (4)	0.0055 (4)
C9	0.0279 (6)	0.0468 (8)	0.0460 (8)	0.0078 (5)	0.0147 (5)	0.0207 (6)
C10	0.0345 (6)	0.0420 (7)	0.0413 (7)	0.0059 (5)	0.0139 (5)	0.0202 (6)
C11	0.0303 (6)	0.0269 (5)	0.0291 (5)	0.0035 (4)	0.0036 (4)	0.0042 (4)
C12	0.0266 (6)	0.0461 (7)	0.0417 (7)	0.0067 (5)	0.0114 (5)	0.0158 (6)
C13	0.0295 (6)	0.0415 (7)	0.0364 (6)	0.0036 (5)	0.0109 (5)	0.0159 (5)

Geometric parameters (Å, º)

S1—O4	1.4271 (10)	C4—H4	0.93
S1—O3	1.4293 (10)	C5—C6	1.380 (2)
S1—N1	1.6287 (11)	C5—H5	0.93
S1—C8	1.7733 (12)	C6—C7	1.378 (2)
O1—C1	1.3128 (15)	C6—H6	0.93
O1—H1	0.82	C7—H7	0.93
O2—C1	1.2368 (16)	C8—C13	1.3821 (17)
O5—N2	1.2226 (16)	C8—C9	1.3919 (17)
O6—N2	1.2232 (16)	C9—C10	1.3818 (19)
N1—C3	1.4109 (16)	C9—H9	0.93
N1—H1N	0.8488	C10—C11	1.3771 (18)
N2—C11	1.4742 (16)	C10—H10	0.93
C1—C2	1.4745 (17)	C11—C12	1.3758 (18)
C2—C7	1.3988 (18)	C12—C13	1.3869 (19)
C2—C3	1.4091 (16)	C12—H12	0.93
C3—C4	1.3950 (17)	C13—H13	0.93
C4—C5	1.381 (2)
O4—S1—O3	120.22 (6)	C6—C5—H5	119.7
O4—S1—N1	109.78 (6)	C4—C5—H5	119.7
O3—S1—N1	104.49 (6)	C7—C6—C5	119.39 (13)
O4—S1—C8	107.12 (6)	C7—C6—H6	120.3
O3—S1—C8	108.39 (6)	C5—C6—H6	120.3
N1—S1—C8	106.03 (6)	C6—C7—C2	121.45 (13)
C1—O1—H1	109.5	C6—C7—H7	119.3
C3—N1—S1	126.42 (8)	C2—C7—H7	119.3
C3—N1—H1N	113.2	C13—C8—C9	121.35 (12)
S1—N1—H1N	114.7	C13—C8—S1	119.98 (10)
O5—N2—O6	124.50 (12)	C9—C8—S1	118.67 (9)
O5—N2—C11	117.92 (12)	C10—C9—C8	119.56 (12)
O6—N2—C11	117.58 (12)	C10—C9—H9	120.2
O2—C1—O1	121.85 (11)	C8—C9—H9	120.2
O2—C1—C2	123.80 (11)	C11—C10—C9	118.42 (12)
O1—C1—C2	114.34 (11)	C11—C10—H10	120.8
C7—C2—C3	118.68 (11)	C9—C10—H10	120.8
C7—C2—C1	118.77 (11)	C12—C11—C10	122.67 (12)
C3—C2—C1	122.55 (11)	C12—C11—N2	118.86 (11)
C4—C3—C2	119.19 (11)	C10—C11—N2	118.47 (12)
C4—C3—N1	121.53 (11)	C11—C12—C13	119.04 (12)
C2—C3—N1	119.27 (10)	C11—C12—H12	120.5
C5—C4—C3	120.56 (13)	C13—C12—H12	120.5
C5—C4—H4	119.7	C8—C13—C12	118.95 (12)
C3—C4—H4	119.7	C8—C13—H13	120.5
C6—C5—C4	120.67 (13)	C12—C13—H13	120.5
O4—S1—N1—C3	57.75 (12)	O4—S1—C8—C13	−17.03 (12)
O3—S1—N1—C3	−172.05 (10)	O3—S1—C8—C13	−148.14 (11)
C8—S1—N1—C3	−57.63 (12)	N1—S1—C8—C13	100.16 (11)
O2—C1—C2—C7	179.10 (13)	O4—S1—C8—C9	162.39 (11)
O1—C1—C2—C7	−0.05 (17)	O3—S1—C8—C9	31.28 (12)
O2—C1—C2—C3	−0.3 (2)	N1—S1—C8—C9	−80.42 (12)
O1—C1—C2—C3	−179.48 (11)	C13—C8—C9—C10	−1.3 (2)
C7—C2—C3—C4	0.65 (18)	S1—C8—C9—C10	179.30 (11)
C1—C2—C3—C4	−179.91 (11)	C8—C9—C10—C11	0.3 (2)
C7—C2—C3—N1	179.55 (11)	C9—C10—C11—C12	0.3 (2)
C1—C2—C3—N1	−1.01 (17)	C9—C10—C11—N2	−179.56 (12)
S1—N1—C3—C4	−32.39 (17)	O5—N2—C11—C12	167.21 (13)
S1—N1—C3—C2	148.74 (10)	O6—N2—C11—C12	−13.63 (18)
C2—C3—C4—C5	−2.0 (2)	O5—N2—C11—C10	−12.89 (18)
N1—C3—C4—C5	179.15 (12)	O6—N2—C11—C10	166.27 (13)
C3—C4—C5—C6	1.4 (2)	C10—C11—C12—C13	−0.1 (2)
C4—C5—C6—C7	0.5 (2)	N2—C11—C12—C13	179.83 (12)
C5—C6—C7—C2	−1.8 (2)	C9—C8—C13—C12	1.6 (2)
C3—C2—C7—C6	1.3 (2)	S1—C8—C13—C12	−179.04 (11)
C1—C2—C7—C6	−178.20 (13)	C11—C12—C13—C8	−0.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.86	2.6766 (14)	174
C5—H5···O4^ii	0.93	2.6	3.5150 (17)	170
C9—H9···O6^iii	0.93	2.6	3.3511 (18)	138

Symmetry codes: (i) −x−1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z.

(AgL)

Crystal data

[Ag(C13H9N2O6S)]	F(000) = 848
Mr = 429.15	Dx = 2.088 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8451 reflections
a = 19.9216 (7) Å	θ = 3.1–26.7°
b = 5.2391 (2) Å	µ = 1.67 mm^−1
c = 13.0860 (4) Å	T = 293 K
β = 91.864 (3)°	Irregular, colourless
V = 1365.08 (8) Å^3	0.21 × 0.18 × 0.17 mm
Z = 4

Data collection

Rigaku Xcalibur, Atlas, Gemini ultra diffractometer	3553 independent reflections
Graphite monochromator	2723 reflections with I > 2σ(I)
Detector resolution: 10.4186 pixels mm^-1	Rint = 0.046
ω scans	θmax = 29.5°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	h = −27→26
Tmin = 0.601, Tmax = 1.000	k = −7→7
22926 measured reflections	l = −18→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0311P)^2 + 1.0461P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3553 reflections	Δρmax = 0.82 e Å^−3
208 parameters	Δρmin = −0.78 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Single-crystal X-ray diffraction measurements were performed on an Agilent–Gemini diffractometer equipped with a CCD area detector using MoK? (0.71073 Å) radiation. The CrysAlisPro software package (Rigaku, 2015) was used for data collection and reduction (Oxford Diffraction Ltda, version 171.38.41). The structures were solved by direct methods using SHELXS-97 and refined by full-matrix least squares on F² using SHELXL-2018 (Sheldrick, 2015). All non-hydrogen atoms were refined using anisotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ag1	0.45005 (2)	1.02405 (5)	0.25327 (2)	0.04349 (10)
S1	0.23113 (4)	0.89424 (14)	0.01834 (6)	0.03421 (18)
O1	0.47283 (10)	0.3610 (4)	0.13073 (16)	0.0406 (5)
O2	0.41107 (11)	0.7127 (4)	0.14202 (16)	0.0445 (5)
O3	0.23823 (11)	1.0962 (4)	0.09090 (18)	0.0451 (6)
O4	0.21229 (12)	0.9467 (4)	−0.08584 (18)	0.0482 (6)
O5	0.05200 (13)	0.0407 (5)	0.2615 (2)	0.0599 (7)
O6	−0.00680 (14)	0.0579 (5)	0.1205 (2)	0.0663 (8)
N1	0.30383 (12)	0.7539 (5)	0.02430 (19)	0.0351 (6)
H1N	0.33012	0.786538	0.075391	0.042*
N2	0.04063 (14)	0.1248 (5)	0.1763 (2)	0.0448 (7)
C1	0.42645 (14)	0.5073 (5)	0.0991 (2)	0.0315 (6)
C2	0.38807 (13)	0.4301 (5)	0.0032 (2)	0.0282 (6)
C3	0.32950 (14)	0.5556 (5)	−0.0338 (2)	0.0299 (6)
C4	0.29988 (17)	0.4801 (6)	−0.1271 (2)	0.0420 (8)
H4	0.261568	0.563509	−0.152159	0.05*
C5	0.32676 (17)	1.2170 (6)	0.3173 (2)	0.0450 (8)
H5	0.306998	1.262994	0.254646	0.054*
C6	0.38302 (17)	1.3464 (6)	0.3546 (2)	0.0420 (8)
H6	0.400465	1.482049	0.318074	0.05*
C7	0.41304 (15)	1.2716 (5)	0.4467 (2)	0.0358 (7)
H7	0.450893	1.358491	0.471398	0.043*
C8	0.17263 (14)	0.6715 (5)	0.0643 (2)	0.0309 (6)
C9	0.17305 (15)	0.6189 (6)	0.1683 (2)	0.0376 (7)
H9	0.202846	0.703349	0.212837	0.045*
C10	0.12919 (16)	0.4414 (6)	0.2050 (2)	0.0385 (7)
H10	0.128829	0.403094	0.274379	0.046*
C11	0.08587 (14)	0.3220 (6)	0.1366 (2)	0.0347 (7)
C12	0.08370 (15)	0.3743 (6)	0.0338 (2)	0.0409 (7)
H12	0.053164	0.291552	−0.01005	0.049*
C13	0.12790 (16)	0.5524 (6)	−0.0029 (2)	0.0397 (7)
H13	0.127533	0.591882	−0.072238	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.04819 (17)	0.04274 (16)	0.03908 (16)	−0.00480 (11)	−0.00562 (11)	−0.00134 (11)
S1	0.0330 (4)	0.0303 (4)	0.0392 (4)	0.0023 (3)	−0.0008 (3)	0.0045 (3)
O1	0.0330 (11)	0.0440 (12)	0.0444 (13)	−0.0003 (9)	−0.0045 (9)	0.0083 (10)
O2	0.0459 (13)	0.0461 (13)	0.0406 (13)	0.0017 (10)	−0.0098 (10)	−0.0123 (11)
O3	0.0450 (13)	0.0298 (11)	0.0605 (15)	0.0014 (9)	0.0011 (11)	−0.0065 (11)
O4	0.0484 (14)	0.0511 (14)	0.0449 (14)	0.0014 (11)	−0.0049 (11)	0.0193 (11)
O5	0.0645 (18)	0.0561 (16)	0.0593 (18)	−0.0083 (12)	0.0054 (14)	0.0165 (13)
O6	0.0653 (18)	0.0734 (18)	0.0604 (17)	−0.0333 (15)	0.0068 (14)	−0.0132 (14)
N1	0.0314 (13)	0.0384 (14)	0.0350 (14)	0.0029 (10)	−0.0049 (10)	−0.0071 (11)
N2	0.0419 (16)	0.0411 (15)	0.0520 (18)	−0.0050 (12)	0.0104 (13)	−0.0079 (14)
C1	0.0263 (14)	0.0366 (16)	0.0317 (15)	−0.0057 (12)	0.0044 (11)	0.0058 (13)
C2	0.0276 (14)	0.0300 (14)	0.0271 (14)	−0.0056 (11)	0.0050 (11)	0.0025 (11)
C3	0.0319 (15)	0.0309 (14)	0.0272 (14)	−0.0068 (11)	0.0037 (11)	0.0021 (11)
C4	0.0436 (18)	0.050 (2)	0.0323 (16)	−0.0041 (14)	−0.0059 (13)	−0.0014 (14)
C5	0.057 (2)	0.050 (2)	0.0287 (16)	0.0137 (16)	0.0040 (14)	0.0086 (14)
C6	0.052 (2)	0.0372 (17)	0.0374 (18)	0.0081 (14)	0.0151 (15)	0.0062 (14)
C7	0.0376 (16)	0.0327 (15)	0.0378 (17)	0.0021 (12)	0.0104 (13)	−0.0008 (13)
C8	0.0303 (15)	0.0302 (14)	0.0320 (15)	0.0046 (11)	−0.0012 (11)	0.0001 (12)
C9	0.0390 (17)	0.0404 (17)	0.0334 (16)	−0.0044 (13)	−0.0010 (13)	−0.0055 (13)
C10	0.0435 (18)	0.0437 (18)	0.0284 (16)	−0.0035 (14)	0.0040 (13)	−0.0014 (13)
C11	0.0320 (15)	0.0344 (16)	0.0380 (17)	0.0003 (12)	0.0049 (12)	−0.0034 (13)
C12	0.0373 (17)	0.0449 (18)	0.0401 (18)	−0.0048 (14)	−0.0063 (13)	−0.0047 (15)
C13	0.0397 (17)	0.0492 (18)	0.0299 (16)	−0.0012 (14)	−0.0040 (13)	0.0024 (14)

Geometric parameters (Å, º)

Ag1—O1^i	2.290 (2)	C2—C7^iv	1.391 (4)
Ag1—O2	2.304 (2)	C2—C3	1.411 (4)
Ag1—O1^ii	2.437 (2)	C3—C4	1.396 (4)
Ag1—C6	2.551 (3)	C4—C5^iv	1.381 (5)
Ag1—Ag1^i	3.2926 (3)	C4—H4	0.93
Ag1—Ag1^iii	3.2926 (3)	C5—C6	1.385 (5)
S1—O3	1.426 (2)	C5—H5	0.93
S1—O3	1.426 (2)	C6—C7	1.385 (4)
S1—O4	1.429 (2)	C6—H6	0.93
S1—N1	1.624 (2)	C7—H7	0.93
S1—C8	1.768 (3)	C8—C13	1.380 (4)
O1—C1	1.260 (3)	C8—C9	1.389 (4)
O2—C1	1.256 (3)	C9—C10	1.373 (4)
O3—O3	0.000 (4)	C9—H9	0.93
O5—N2	1.214 (4)	C10—C11	1.373 (4)
O6—N2	1.226 (4)	C10—H10	0.93
N1—C3	1.394 (4)	C11—C12	1.372 (4)
N1—H1N	0.8531	C12—C13	1.381 (4)
N2—C11	1.476 (4)	C12—H12	0.93
C1—C2	1.504 (4)	C13—H13	0.93
O1^i—Ag1—O2	111.09 (8)	C7^iv—C2—C3	118.5 (3)
O1^i—Ag1—O1^ii	124.83 (6)	C7^iv—C2—C1	117.9 (3)
O2—Ag1—O1^ii	99.39 (8)	C3—C2—C1	123.6 (3)
O1^i—Ag1—C6	104.70 (9)	N1—C3—C4	122.4 (3)
O2—Ag1—C6	128.73 (10)	N1—C3—C2	118.3 (2)
O1^ii—Ag1—C6	88.52 (9)	C4—C3—C2	119.3 (3)
O1^i—Ag1—Ag1^i	85.46 (6)	C5^iv—C4—C3	120.8 (3)
O2—Ag1—Ag1^i	137.59 (6)	C5^iv—C4—H4	119.6
O1^ii—Ag1—Ag1^i	44.04 (5)	C3—C4—H4	119.6
C6—Ag1—Ag1^i	79.27 (8)	C4^vi—C5—C6	120.3 (3)
O1^i—Ag1—Ag1^iii	47.72 (5)	C4^vi—C5—H5	119.9
O2—Ag1—Ag1^iii	67.17 (5)	C6—C5—H5	119.9
O1^ii—Ag1—Ag1^iii	115.69 (5)	C7—C6—C5	119.3 (3)
C6—Ag1—Ag1^iii	150.14 (7)	C7—C6—Ag1	92.67 (19)
Ag1^i—Ag1—Ag1^iii	105.420 (14)	C5—C6—Ag1	85.7 (2)
O3—S1—O3	0.00 (18)	C7—C6—H6	120.3
O3—S1—O4	120.67 (14)	C5—C6—H6	120.3
O3—S1—O4	120.67 (14)	Ag1—C6—H6	91.6
O3—S1—N1	103.59 (13)	C6—C7—C2^vi	121.7 (3)
O3—S1—N1	103.59 (13)	C6—C7—H7	119.1
O4—S1—N1	109.82 (14)	C2^vi—C7—H7	119.1
O3—S1—C8	108.40 (14)	C13—C8—C9	121.2 (3)
O3—S1—C8	108.40 (14)	C13—C8—S1	120.0 (2)
O4—S1—C8	107.19 (14)	C9—C8—S1	118.7 (2)
N1—S1—C8	106.35 (13)	C10—C9—C8	119.6 (3)
C1—O1—Ag1^iii	117.37 (19)	C10—C9—H9	120.2
C1—O1—Ag1^v	120.41 (18)	C8—C9—H9	120.2
Ag1^iii—O1—Ag1^v	88.24 (7)	C9—C10—C11	118.3 (3)
C1—O2—Ag1	143.8 (2)	C9—C10—H10	120.8
O3—O3—S1	0 (10)	C11—C10—H10	120.8
C3—N1—S1	130.8 (2)	C12—C11—C10	123.1 (3)
C3—N1—H1N	110.5	C12—C11—N2	118.9 (3)
S1—N1—H1N	118.1	C10—C11—N2	117.9 (3)
O5—N2—O6	124.1 (3)	C11—C12—C13	118.5 (3)
O5—N2—C11	118.6 (3)	C11—C12—H12	120.8
O6—N2—C11	117.3 (3)	C13—C12—H12	120.8
O2—C1—O1	124.2 (3)	C8—C13—C12	119.3 (3)
O2—C1—C2	118.6 (3)	C8—C13—H13	120.4
O1—C1—C2	117.3 (3)	C12—C13—H13	120.4
O4—S1—O3—O3	0.0 (6)	C4^vi—C5—C6—Ag1	92.3 (3)
N1—S1—O3—O3	0.0 (6)	C5—C6—C7—C2^vi	−0.2 (4)
C8—S1—O3—O3	0.0 (6)	Ag1—C6—C7—C2^vi	−86.7 (3)
O3—S1—N1—C3	−174.6 (3)	O3—S1—C8—C13	142.3 (2)
O3—S1—N1—C3	−174.6 (3)	O3—S1—C8—C13	142.3 (2)
O4—S1—N1—C3	−44.4 (3)	O4—S1—C8—C13	10.5 (3)
C8—S1—N1—C3	71.3 (3)	N1—S1—C8—C13	−106.9 (3)
Ag1—O2—C1—O1	20.5 (5)	O3—S1—C8—C9	−38.1 (3)
Ag1—O2—C1—C2	−158.7 (2)	O3—S1—C8—C9	−38.1 (3)
Ag1^iii—O1—C1—O2	−16.2 (4)	O4—S1—C8—C9	−169.8 (2)
Ag1^v—O1—C1—O2	89.1 (3)	N1—S1—C8—C9	72.8 (3)
Ag1^iii—O1—C1—C2	163.05 (17)	C13—C8—C9—C10	1.4 (5)
Ag1^v—O1—C1—C2	−91.7 (3)	S1—C8—C9—C10	−178.3 (2)
O2—C1—C2—C7^iv	168.7 (2)	C8—C9—C10—C11	−0.3 (5)
O1—C1—C2—C7^iv	−10.6 (4)	C9—C10—C11—C12	−1.0 (5)
O2—C1—C2—C3	−9.4 (4)	C9—C10—C11—N2	177.8 (3)
O1—C1—C2—C3	171.3 (2)	O5—N2—C11—C12	164.6 (3)
S1—N1—C3—C4	15.8 (4)	O6—N2—C11—C12	−16.0 (4)
S1—N1—C3—C2	−165.0 (2)	O5—N2—C11—C10	−14.3 (4)
C7^iv—C2—C3—N1	178.6 (2)	O6—N2—C11—C10	165.1 (3)
C1—C2—C3—N1	−3.3 (4)	C10—C11—C12—C13	1.1 (5)
C7^iv—C2—C3—C4	−2.2 (4)	N2—C11—C12—C13	−177.7 (3)
C1—C2—C3—C4	175.9 (3)	C9—C8—C13—C12	−1.3 (5)
N1—C3—C4—C5^iv	179.9 (3)	S1—C8—C13—C12	178.4 (2)
C2—C3—C4—C5^iv	0.7 (4)	C11—C12—C13—C8	0.1 (5)
C4^vi—C5—C6—C7	1.7 (5)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+1/2; (iv) x, −y+3/2, z−1/2; (v) x, y−1, z; (vi) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3	0.93	2.65	3.457 (4)	145
C13—H13···O5^vii	0.93	2.7	3.424 (4)	136
C12—H12···O6^viii	0.93	2.49	3.369 (4)	157
N1—H1N···O2	0.85	1.85	2.602 (3)	146
C4—H4···O4	0.93	2.41	3.062 (4)	127

Symmetry codes: (vii) x, −y+1/2, z−1/2; (viii) −x, −y, −z.