Bis[μ-1,2-bis­(1H-imidazol-1-ylmeth­yl)benzene-κ²N:N′]disilver(I) bis­(4-amino­benzene­sulfonate) hexa­hydrate

In the binuclear cation of the title compound, [Ag₂(C₁₄H₁₄N₄)₂](C₆H₆NO₃S)₂·6H₂O, two Ag^I atoms are bridged by two 1,2-bis­[(1H-imidazol-1-yl)meth­yl]benzene (IBI) ligands to form a 22-membered ring with crystallographic twofold rotation symmetry. Each Ag^I atom is two-coordinate, with a slightly distorted linear coordination geometry. The sulfonate anion does not coordinate to the silver ion but acts as a counteranion.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.091
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       OW2    -   H2B    ...          ?

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.02
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ag1    -   N4      ..       5.50 su
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H2N    ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O

Alert level G
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 .......         11

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Over the past decades, the design and synthesis of Ag(I) compounds have attracted great attention because of the versatility of their coordination geometries (Aakeröy & Beatty, 1998; Smith et al., 1996). In particular, silver-sulfonate complexes have attracted great attention by reason of their abilities to form inorganic-organic lamellar structures and intercalate guest molecules (Shimizu et al., 1998; Cote & Shimizu, 2004; Liu et al., 2007). In this paper, the synthesis and the crystal structure of a novel silver-sulfonate complex (I) [Ag₂(IBI)₂]L₂ ^. 6H₂O (IBI = 1,2-bis ((1H-imidazol-1-yl)methyl)benzene and L = p-aminobenzenesulfonic acid) is presented.

The molecular structure of (I) is shown in Fig.1. Selected bond distances and angles are listed in Table 1. The compound (I) shows a binuclear structure, where each of Ag(I) atoms has a slightly distorted linear geometry and is coordinated by two N atoms from the IBI ligands. The Ag—N (IBI) distances in (I) are near to that in the related compounds (Li et al., 2006). Notably, the L ligand does not coordinate to the Ag(I) center, acting as a counter-anion. Finally, N—H···O and O—H···O hydrogen bonds between water molecules and the L ligands result in the formation of a three-dimensional network (Table 2).

Related literature

For studies on silver sulfonates, see Liu et al. (2007) and Li et al. (2006).

For related literature, see: Aakeröy & Beatty (1998); Cote & Shimizu (2004); Shimizu et al. (1998); Smith et al. (1996).

S2. Experimental

An aqueous solution (10 ml) of p-aminobenzenesulfonic acid (0.5 mmol) was added to solid Ag₂CO₃ (0.25 mmol) and stirred for several minutes until no further CO₂ was given off. The 1-(3-(1H-imidazol-1-yl)methyl)benzyl)-1H-imidazole (0.5 mmol) was then added and a precipitate was formed. The precipitate was dissolved by ammonium hydroxide. Crystals of (I) were obtained by evaporation of the solution for several days at room temperature.

S3. Refinement

H atoms bonded to N atom were located in a difference map and refined with distance restraints of N—H = 0.85±0.01 Å. H atoms bonded to C atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with U_iso(H) = 1.2U_eq(carrier). H atoms bonded to O atoms of water molecules were located in a difference Fourier map and refined isotropically with distance restraints of O—H = 0.85±0.01 Å and H···H = 1.3±0.01 Å, with U_iso(H) = 1.5 U_eq(N).

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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).

Figures

Fig. 1. The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) -x + 1, -y + 2, -z + 1.

Bis[µ-1,2-bis(1H-imidazol-1-ylmethyl)benzene- κ²N,N']disilver(I)] bis(4-aminobenzenesulfonate) hexahydrate

Crystal data

[Ag2(C14H14N4)2](C6H6NO3S)2·6H2O	F(000) = 2336
Mr = 1144.78	Dx = 1.666 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5221 reflections
a = 14.842 (3) Å	θ = 3.1–27.5°
b = 16.283 (3) Å	µ = 1.02 mm^−1
c = 19.527 (4) Å	T = 293 K
β = 104.76 (3)°	Block, colorless
V = 4563.6 (16) Å^3	0.27 × 0.26 × 0.19 mm
Z = 4

Data collection

Rigaku RAXIS-RAPID diffractometer	5221 independent reflections
Radiation source: fine-focus sealed tube	4333 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −19→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −20→21
Tmin = 0.698, Tmax = 0.811	l = −25→25
22007 measured 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0469P)^2 + 5.1924P] where P = (Fo^2 + 2Fc^2)/3
5221 reflections	(Δ/σ)max = 0.004
324 parameters	Δρmax = 0.91 e Å^−3
11 restraints	Δρmin = −0.49 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
Ag1	0.449998 (13)	1.092109 (13)	0.518907 (12)	0.04061 (9)
C1	0.18894 (16)	0.84749 (15)	0.31821 (13)	0.0290 (5)
H1AA	0.1922	0.7939	0.2973	0.035*
H2AA	0.1956	0.8887	0.2840	0.035*
C2	0.73559 (17)	1.15989 (15)	0.54897 (13)	0.0319 (5)
H2	0.7865	1.1780	0.5335	0.038*
C3	0.09499 (15)	0.85728 (14)	0.33396 (12)	0.0256 (5)
C4	0.26422 (17)	1.05237 (15)	0.41358 (14)	0.0321 (5)
H4	0.2926	1.0561	0.3764	0.039*
C5	−0.03160 (17)	0.93772 (16)	0.35446 (13)	0.0329 (5)
H5	−0.0578	0.9886	0.3593	0.040*
C6	0.05636 (15)	0.93418 (14)	0.34222 (12)	0.0257 (5)
C7	0.16588 (19)	0.85770 (15)	0.66231 (14)	0.0347 (6)
C8	0.0204 (2)	0.78904 (17)	0.65491 (16)	0.0422 (6)
H8	−0.0197	0.7628	0.6775	0.051*
C9	−0.0061 (2)	0.79756 (15)	0.58140 (16)	0.0387 (6)
C10	0.10692 (17)	1.01380 (14)	0.33853 (13)	0.0312 (5)
H10A	0.1393	1.0100	0.3013	0.037*
H10B	0.0618	1.0580	0.3264	0.037*
C11	0.15902 (17)	1.03440 (16)	0.47255 (14)	0.0343 (5)
H11	0.1030	1.0236	0.4840	0.041*
C12	−0.08107 (17)	0.86696 (18)	0.35968 (14)	0.0362 (6)
H12	−0.1400	0.8703	0.3679	0.043*
C13	0.64699 (16)	1.12020 (16)	0.61609 (14)	0.0310 (5)
H13	0.6271	1.1062	0.6560	0.037*
C14	0.04452 (17)	0.78665 (15)	0.33941 (14)	0.0324 (5)
H14	0.0698	0.7355	0.3341	0.039*
C15	0.1045 (2)	0.81852 (16)	0.69489 (15)	0.0402 (6)
H15	0.1202	0.8122	0.7438	0.048*
C16	−0.04243 (18)	0.79123 (17)	0.35252 (14)	0.0372 (6)
H16	−0.0750	0.7434	0.3565	0.045*
C17	0.0561 (2)	0.83721 (17)	0.54977 (15)	0.0422 (6)
H17	0.0405	0.8438	0.5009	0.051*
C18	0.24085 (17)	1.05413 (17)	0.51802 (14)	0.0358 (6)
H18	0.2508	1.0594	0.5668	0.043*
C19	0.1406 (2)	0.86694 (17)	0.58966 (15)	0.0389 (6)
H19	0.1807	0.8934	0.5673	0.047*
C20	0.64898 (17)	1.14382 (16)	0.50806 (14)	0.0344 (5)
H20	0.6303	1.1489	0.4590	0.041*
N1	−0.0886 (2)	0.76439 (16)	0.54189 (17)	0.0481 (6)
H1N	−0.132 (2)	0.760 (3)	0.563 (2)	0.084 (15)*
H2N	−0.109 (3)	0.783 (3)	0.4999 (10)	0.080 (14)*
N2	0.17443 (13)	1.03327 (11)	0.40591 (11)	0.0268 (4)
N3	0.73354 (13)	1.14420 (11)	0.61745 (10)	0.0244 (4)
N4	0.30739 (14)	1.06528 (13)	0.48088 (12)	0.0339 (5)
N5	0.59315 (14)	1.11888 (13)	0.55039 (12)	0.0313 (4)
O1	0.29951 (17)	0.85170 (14)	0.77672 (12)	0.0566 (6)
O2	0.25394 (14)	0.98490 (12)	0.72646 (12)	0.0474 (5)
O3	0.33681 (15)	0.89252 (13)	0.66753 (12)	0.0497 (5)
S1	0.27191 (5)	0.89939 (4)	0.71192 (4)	0.03645 (15)
OW1	0.2289 (2)	0.74243 (17)	0.87271 (17)	0.0708 (7)
H1B	0.243 (4)	0.774 (3)	0.842 (2)	0.106*
H1A	0.202 (3)	0.701 (2)	0.850 (3)	0.106*
OW2	0.3692 (4)	1.10983 (19)	0.7022 (2)	0.1041 (13)
H2A	0.331 (3)	1.072 (3)	0.703 (4)	0.156*
H2B	0.421 (2)	1.085 (3)	0.712 (4)	0.156*
OW3	0.5016 (4)	0.9682 (4)	0.6533 (2)	0.167 (3)
H3A	0.445 (2)	0.983 (5)	0.638 (4)	0.250*
H3B	0.496 (7)	0.929 (4)	0.680 (4)	0.250*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.02279 (11)	0.04981 (14)	0.04500 (14)	−0.00688 (7)	0.00086 (8)	−0.00582 (9)
C1	0.0220 (11)	0.0381 (12)	0.0248 (12)	0.0044 (8)	0.0022 (9)	−0.0043 (9)
C2	0.0251 (12)	0.0412 (13)	0.0291 (12)	−0.0012 (9)	0.0062 (10)	0.0036 (10)
C3	0.0201 (11)	0.0311 (11)	0.0220 (11)	0.0015 (8)	−0.0010 (8)	−0.0034 (9)
C4	0.0282 (12)	0.0318 (12)	0.0370 (14)	−0.0042 (9)	0.0094 (10)	−0.0011 (10)
C5	0.0251 (12)	0.0416 (13)	0.0283 (12)	0.0083 (9)	−0.0002 (9)	−0.0088 (10)
C6	0.0213 (11)	0.0304 (11)	0.0214 (11)	0.0017 (8)	−0.0019 (8)	−0.0040 (9)
C7	0.0453 (15)	0.0265 (11)	0.0358 (14)	0.0102 (10)	0.0165 (12)	0.0000 (10)
C8	0.0500 (17)	0.0365 (14)	0.0460 (16)	−0.0001 (11)	0.0227 (14)	0.0025 (12)
C9	0.0464 (16)	0.0290 (12)	0.0427 (15)	0.0064 (10)	0.0151 (12)	−0.0049 (11)
C10	0.0315 (12)	0.0298 (11)	0.0276 (12)	0.0018 (9)	−0.0010 (10)	0.0011 (9)
C11	0.0272 (12)	0.0429 (13)	0.0336 (13)	0.0003 (10)	0.0092 (10)	−0.0071 (11)
C12	0.0199 (11)	0.0568 (16)	0.0309 (13)	−0.0026 (10)	0.0048 (10)	−0.0062 (12)
C13	0.0232 (11)	0.0395 (12)	0.0310 (12)	−0.0010 (9)	0.0080 (10)	−0.0025 (10)
C14	0.0289 (12)	0.0311 (12)	0.0335 (13)	−0.0007 (9)	0.0014 (10)	−0.0070 (10)
C15	0.0535 (17)	0.0386 (14)	0.0329 (14)	0.0074 (11)	0.0192 (12)	0.0033 (11)
C16	0.0279 (13)	0.0459 (14)	0.0341 (14)	−0.0114 (10)	0.0010 (10)	−0.0030 (11)
C17	0.0531 (17)	0.0447 (15)	0.0313 (14)	0.0009 (12)	0.0152 (13)	0.0001 (11)
C18	0.0291 (13)	0.0448 (14)	0.0322 (13)	−0.0001 (10)	0.0053 (10)	−0.0109 (11)
C19	0.0465 (16)	0.0397 (14)	0.0358 (14)	0.0012 (11)	0.0200 (12)	0.0004 (11)
C20	0.0292 (13)	0.0431 (14)	0.0281 (12)	0.0003 (10)	0.0024 (10)	0.0015 (10)
N1	0.0451 (15)	0.0444 (14)	0.0557 (17)	0.0000 (11)	0.0141 (13)	−0.0051 (13)
N2	0.0242 (9)	0.0254 (9)	0.0289 (10)	−0.0003 (7)	0.0032 (8)	−0.0026 (8)
N3	0.0194 (9)	0.0280 (9)	0.0250 (10)	0.0024 (7)	0.0043 (7)	−0.0013 (7)
N4	0.0272 (11)	0.0335 (10)	0.0393 (12)	−0.0019 (8)	0.0051 (9)	−0.0037 (9)
N5	0.0238 (10)	0.0352 (10)	0.0334 (11)	0.0020 (8)	0.0044 (8)	−0.0024 (9)
O1	0.0655 (15)	0.0591 (13)	0.0405 (12)	0.0144 (11)	0.0052 (11)	0.0087 (10)
O2	0.0445 (11)	0.0367 (10)	0.0614 (14)	0.0059 (8)	0.0144 (10)	−0.0101 (9)
O3	0.0419 (12)	0.0608 (13)	0.0496 (13)	0.0099 (9)	0.0177 (10)	−0.0103 (10)
S1	0.0411 (4)	0.0358 (3)	0.0335 (3)	0.0124 (2)	0.0114 (3)	−0.0012 (3)
OW1	0.0701 (18)	0.0705 (17)	0.083 (2)	0.0168 (13)	0.0392 (16)	0.0159 (15)
OW2	0.160 (4)	0.0675 (19)	0.082 (2)	−0.043 (2)	0.024 (3)	−0.0034 (17)
OW3	0.179 (4)	0.240 (6)	0.075 (3)	−0.151 (4)	0.020 (3)	0.016 (3)

Geometric parameters (Å, º)

Ag1—N5	2.102 (2)	C11—N2	1.378 (3)
Ag1—N4	2.103 (2)	C11—H11	0.9300
C1—N3^i	1.478 (3)	C12—C16	1.382 (4)
C1—C3	1.511 (3)	C12—H12	0.9300
C1—H1AA	0.9700	C13—N5	1.328 (3)
C1—H2AA	0.9700	C13—N3	1.336 (3)
C2—C20	1.355 (4)	C13—H13	0.9300
C2—N3	1.369 (3)	C14—C16	1.380 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C14	1.391 (3)	C15—H15	0.9300
C3—C6	1.404 (3)	C16—H16	0.9300
C4—N4	1.324 (3)	C17—C19	1.384 (4)
C4—N2	1.339 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—N4	1.378 (3)
C5—C12	1.384 (4)	C18—H18	0.9300
C5—C6	1.387 (3)	C19—H19	0.9300
C5—H5	0.9300	C20—N5	1.373 (3)
C6—C10	1.509 (3)	C20—H20	0.9300
C7—C19	1.380 (4)	N1—H1N	0.85 (3)
C7—C15	1.392 (4)	N1—H2N	0.85 (3)
C7—S1	1.761 (3)	N3—C1^i	1.478 (3)
C8—C15	1.379 (4)	O1—S1	1.452 (2)
C8—C9	1.395 (4)	O2—S1	1.459 (2)
C8—H8	0.9300	O3—S1	1.455 (2)
C9—N1	1.380 (4)	OW1—H1B	0.86 (5)
C9—C17	1.393 (4)	OW1—H1A	0.85 (4)
C10—N2	1.471 (3)	OW2—H2A	0.84 (5)
C10—H10A	0.9700	OW2—H2B	0.85 (4)
C10—H10B	0.9700	OW3—H3A	0.85 (5)
C11—C18	1.348 (4)	OW3—H3B	0.84 (7)
N5—Ag1—N4	176.46 (9)	C16—C14—C3	121.1 (2)
N3^i—C1—C3	112.11 (19)	C16—C14—H14	119.4
N3^i—C1—H1AA	109.2	C3—C14—H14	119.4
C3—C1—H1AA	109.2	C8—C15—C7	120.3 (3)
N3^i—C1—H2AA	109.2	C8—C15—H15	119.9
C3—C1—H2AA	109.2	C7—C15—H15	119.9
H1AA—C1—H2AA	107.9	C14—C16—C12	119.9 (2)
C20—C2—N3	106.6 (2)	C14—C16—H16	120.0
C20—C2—H2	126.7	C12—C16—H16	120.0
N3—C2—H2	126.7	C19—C17—C9	121.3 (3)
C14—C3—C6	119.0 (2)	C19—C17—H17	119.3
C14—C3—C1	118.1 (2)	C9—C17—H17	119.3
C6—C3—C1	122.9 (2)	C11—C18—N4	109.3 (2)
N4—C4—N2	111.4 (2)	C11—C18—H18	125.3
N4—C4—H4	124.3	N4—C18—H18	125.3
N2—C4—H4	124.3	C7—C19—C17	120.7 (3)
C12—C5—C6	121.2 (2)	C7—C19—H19	119.7
C12—C5—H5	119.4	C17—C19—H19	119.7
C6—C5—H5	119.4	C2—C20—N5	109.3 (2)
C5—C6—C3	119.1 (2)	C2—C20—H20	125.4
C5—C6—C10	118.3 (2)	N5—C20—H20	125.4
C3—C6—C10	122.6 (2)	C9—N1—H1N	115 (3)
C19—C7—C15	118.8 (3)	C9—N1—H2N	117 (3)
C19—C7—S1	119.6 (2)	H1N—N1—H2N	111 (4)
C15—C7—S1	121.5 (2)	C4—N2—C11	106.9 (2)
C15—C8—C9	121.7 (3)	C4—N2—C10	125.6 (2)
C15—C8—H8	119.2	C11—N2—C10	127.5 (2)
C9—C8—H8	119.2	C13—N3—C2	107.2 (2)
N1—C9—C17	121.8 (3)	C13—N3—C1^i	125.4 (2)
N1—C9—C8	120.9 (3)	C2—N3—C1^i	127.4 (2)
C17—C9—C8	117.2 (3)	C4—N4—C18	105.7 (2)
N2—C10—C6	112.10 (19)	C4—N4—Ag1	124.93 (18)
N2—C10—H10A	109.2	C18—N4—Ag1	129.30 (18)
C6—C10—H10A	109.2	C13—N5—C20	105.7 (2)
N2—C10—H10B	109.2	C13—N5—Ag1	126.94 (18)
C6—C10—H10B	109.2	C20—N5—Ag1	127.27 (17)
H10A—C10—H10B	107.9	O1—S1—O3	113.29 (14)
C18—C11—N2	106.7 (2)	O1—S1—O2	111.45 (14)
C18—C11—H11	126.7	O3—S1—O2	111.77 (13)
N2—C11—H11	126.7	O1—S1—C7	106.71 (14)
C16—C12—C5	119.6 (2)	O3—S1—C7	106.10 (13)
C16—C12—H12	120.2	O2—S1—C7	107.04 (12)
C5—C12—H12	120.2	H1B—OW1—H1A	106 (5)
N5—C13—N3	111.3 (2)	H2A—OW2—H2B	103 (5)
N5—C13—H13	124.4	H3A—OW3—H3B	101 (9)
N3—C13—H13	124.4
N3^i—C1—C3—C14	−100.7 (2)	N3—C2—C20—N5	0.4 (3)
N3^i—C1—C3—C6	80.3 (3)	N4—C4—N2—C11	0.3 (3)
C12—C5—C6—C3	1.0 (4)	N4—C4—N2—C10	−178.9 (2)
C12—C5—C6—C10	−178.9 (2)	C18—C11—N2—C4	−0.1 (3)
C14—C3—C6—C5	−1.0 (3)	C18—C11—N2—C10	179.0 (2)
C1—C3—C6—C5	178.0 (2)	C6—C10—N2—C4	128.4 (2)
C14—C3—C6—C10	178.8 (2)	C6—C10—N2—C11	−50.6 (3)
C1—C3—C6—C10	−2.1 (3)	N5—C13—N3—C2	0.5 (3)
C15—C8—C9—N1	177.0 (3)	N5—C13—N3—C1^i	180.0 (2)
C15—C8—C9—C17	0.0 (4)	C20—C2—N3—C13	−0.5 (3)
C5—C6—C10—N2	98.1 (2)	C20—C2—N3—C1^i	−180.0 (2)
C3—C6—C10—N2	−81.7 (3)	N2—C4—N4—C18	−0.3 (3)
C6—C5—C12—C16	−0.1 (4)	N2—C4—N4—Ag1	177.37 (15)
C6—C3—C14—C16	0.2 (4)	C11—C18—N4—C4	0.3 (3)
C1—C3—C14—C16	−178.9 (2)	C11—C18—N4—Ag1	−177.31 (18)
C9—C8—C15—C7	−0.3 (4)	N3—C13—N5—C20	−0.3 (3)
C19—C7—C15—C8	0.5 (4)	N3—C13—N5—Ag1	−176.41 (15)
S1—C7—C15—C8	177.7 (2)	C2—C20—N5—C13	−0.1 (3)
C3—C14—C16—C12	0.7 (4)	C2—C20—N5—Ag1	176.04 (17)
C5—C12—C16—C14	−0.8 (4)	C19—C7—S1—O1	−155.0 (2)
N1—C9—C17—C19	−177.0 (3)	C15—C7—S1—O1	27.9 (2)
C8—C9—C17—C19	−0.1 (4)	C19—C7—S1—O3	−33.9 (2)
N2—C11—C18—N4	−0.1 (3)	C15—C7—S1—O3	149.0 (2)
C15—C7—C19—C17	−0.6 (4)	C19—C7—S1—O2	85.6 (2)
S1—C7—C19—C17	−177.7 (2)	C15—C7—S1—O2	−91.5 (2)
C9—C17—C19—C7	0.3 (4)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···OW1^ii	0.85 (3)	2.16 (3)	3.003 (4)	173 (4)
OW1—H1A···OW2^iii	0.85 (4)	1.95 (4)	2.800 (5)	175 (5)
OW3—H3A···O3	0.85 (5)	2.35 (9)	2.815 (4)	115 (8)
OW1—H1B···O1	0.86 (5)	2.12 (5)	2.963 (4)	171 (5)
OW2—H2A···O2	0.84 (5)	1.95 (5)	2.775 (4)	169 (7)

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