Bis(4-methyl-3,5-diphenyl-1H-pyrazole-κN)silver(I) nitrate.

In the title complex, [Ag(C(16)H(14)N(2))(2)]NO(3), the geometry around the Ag(I) ion is T-shaped with two short Ag-N bonds to the pyrazole ligand and one long Ag-O bond to the nitrate anion. The crystal structure is stabilized by inter-molecular N-H⋯O, C-H⋯O and C-H⋯π inter-actions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For background to pyrazolates and their complexes, see, for example; Rasika Dias et al. (2007 ▶); Hossaini Sadr et al. (2004 ▶, 2006 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

[Ag(C16H14N2)2]NO3

M = 638.46

Triclinic,

a = 10.5529 (12) Å

b = 10.8791 (13) Å

c = 12.8396 (15) Å

α = 80.454 (2)°

β = 68.806 (2)°

γ = 82.398 (2)°

V = 1351.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.79 mm−1

T = 100 K

0.45 × 0.25 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.717, T max = 0.940

8897 measured reflections

4588 independent reflections

4127 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.084

S = 1.15

4588 reflections

372 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017776/jh2288sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017776/jh2288Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag(C16H14N2)2]NO3	Z = 2
Mr = 638.46	F(000) = 652
Triclinic, P1	Dx = 1.569 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5529 (12) Å	Cell parameters from 5736 reflections
b = 10.8791 (13) Å	θ = 2.4–28.2°
c = 12.8396 (15) Å	µ = 0.79 mm−1
α = 80.454 (2)°	T = 100 K
β = 68.806 (2)°	Plate, colorless
γ = 82.398 (2)°	0.45 × 0.25 × 0.08 mm
V = 1351.1 (3) Å3

Bruker APEXII CCD area-detector diffractometer	4588 independent reflections
Radiation source: fine-focus sealed tube	4127 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.717, Tmax = 0.940	k = −12→12
8897 measured reflections	l = −15→15

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0396P)2 + 1.0248P] where P = (Fo2 + 2Fc2)/3
4588 reflections	(Δ/σ)max < 0.001
372 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

Experimental. Ratio of minimum to maximum apparent transmission: 0.450769

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
Ag1	0.85303 (2)	0.22645 (2)	0.355819 (18)	0.02035 (9)
N1	0.6565 (2)	0.2852 (2)	0.34356 (19)	0.0160 (5)
N2	0.5557 (2)	0.3086 (2)	0.44095 (19)	0.0190 (5)
H2	0.5622	0.2860	0.5081	0.023*
N3	1.0319 (2)	0.1865 (2)	0.40203 (19)	0.0171 (5)
N4	1.0218 (2)	0.1566 (2)	0.51133 (19)	0.0177 (5)
H4	0.9456	0.1663	0.5687	0.021*
C1	0.6057 (3)	0.3341 (3)	0.2613 (2)	0.0177 (6)
C2	0.4725 (3)	0.3904 (3)	0.3072 (2)	0.0172 (6)
C3	0.4438 (3)	0.3711 (3)	0.4234 (2)	0.0184 (6)
C4	0.3885 (3)	0.4665 (3)	0.2438 (2)	0.0207 (6)
H4A	0.3303	0.4122	0.2305	0.031*
H4B	0.4487	0.5054	0.1714	0.031*
H4C	0.3314	0.5317	0.2879	0.031*
C5	0.6853 (3)	0.3163 (3)	0.1425 (2)	0.0183 (6)
C6	0.8266 (3)	0.3216 (3)	0.0980 (2)	0.0190 (6)
H6	0.8733	0.3430	0.1426	0.023*
C7	0.8994 (3)	0.2956 (3)	−0.0113 (2)	0.0232 (7)
H7	0.9957	0.2982	−0.0405	0.028*
C8	0.8325 (3)	0.2659 (3)	−0.0782 (2)	0.0238 (7)
H8	0.8828	0.2480	−0.1527	0.029*
C9	0.6910 (3)	0.2624 (3)	−0.0350 (2)	0.0235 (7)
H9	0.6445	0.2431	−0.0805	0.028*
C10	0.6181 (3)	0.2871 (3)	0.0747 (2)	0.0218 (6)
H10	0.5219	0.2842	0.1039	0.026*
C11	0.3216 (3)	0.3995 (3)	0.5199 (2)	0.0175 (6)
C12	0.1916 (3)	0.4080 (3)	0.5121 (3)	0.0221 (6)
H12	0.1822	0.4013	0.4425	0.026*
C13	0.0766 (3)	0.4261 (3)	0.6060 (3)	0.0273 (7)
H13	−0.0114	0.4312	0.6005	0.033*
C14	0.0892 (3)	0.4367 (3)	0.7078 (3)	0.0269 (7)
H14	0.0100	0.4497	0.7716	0.032*
C15	0.2172 (3)	0.4285 (3)	0.7166 (3)	0.0271 (7)
H15	0.2256	0.4350	0.7867	0.033*
C16	0.3326 (3)	0.4110 (3)	0.6234 (2)	0.0208 (6)
H16	0.4202	0.4066	0.6296	0.025*
C17	1.1630 (3)	0.1559 (3)	0.3418 (2)	0.0171 (6)
C18	1.2370 (3)	0.1068 (3)	0.4130 (2)	0.0170 (6)
C19	1.1421 (3)	0.1098 (3)	0.5220 (2)	0.0169 (6)
C20	1.3853 (3)	0.0610 (3)	0.3798 (2)	0.0212 (6)
H20A	1.4195	0.0447	0.3011	0.032*
H20B	1.3959	−0.0164	0.4283	0.032*
H20C	1.4372	0.1247	0.3883	0.032*
C21	1.2098 (3)	0.1833 (3)	0.2165 (2)	0.0178 (6)
C22	1.1694 (3)	0.2986 (3)	0.1667 (2)	0.0207 (6)
H22	1.1097	0.3571	0.2129	0.025*
C23	1.2154 (3)	0.3282 (3)	0.0512 (3)	0.0253 (7)
H23	1.1878	0.4073	0.0187	0.030*
C24	1.3016 (3)	0.2440 (3)	−0.0180 (3)	0.0246 (7)
H24	1.3342	0.2653	−0.0975	0.029*
C25	1.3394 (3)	0.1284 (3)	0.0303 (3)	0.0237 (7)
H25	1.3968	0.0694	−0.0167	0.028*
C26	1.2947 (3)	0.0973 (3)	0.1465 (2)	0.0194 (6)
H26	1.3218	0.0176	0.1785	0.023*
C27	1.1550 (3)	0.0741 (2)	0.6337 (2)	0.0153 (6)
C28	1.2747 (3)	0.0907 (3)	0.6517 (2)	0.0200 (6)
H28	1.3497	0.1240	0.5907	0.024*
C29	1.2845 (3)	0.0590 (3)	0.7577 (2)	0.0199 (6)
H29	1.3651	0.0728	0.7694	0.024*
C30	1.1771 (3)	0.0073 (3)	0.8471 (2)	0.0219 (6)
H30	1.1849	−0.0161	0.9193	0.026*
C31	1.0588 (3)	−0.0101 (3)	0.8301 (2)	0.0213 (6)
H31	0.9853	−0.0457	0.8909	0.026*
C32	1.0469 (3)	0.0244 (3)	0.7246 (2)	0.0175 (6)
H32	0.9644	0.0140	0.7144	0.021*
O1	0.2945 (2)	0.7310 (3)	0.42450 (18)	0.0354 (6)
O2	0.4353 (2)	0.7879 (2)	0.25698 (18)	0.0285 (5)
O3	0.2167 (2)	0.8156 (2)	0.29417 (17)	0.0279 (5)
N5	0.3164 (2)	0.7795 (2)	0.32412 (19)	0.0190 (5)

	U11	U22	U33	U12	U13	U23
Ag1	0.01459 (13)	0.02873 (15)	0.01819 (13)	−0.00052 (9)	−0.00718 (9)	−0.00177 (9)
N1	0.0128 (11)	0.0170 (12)	0.0174 (12)	0.0011 (10)	−0.0053 (10)	−0.0021 (9)
N2	0.0179 (12)	0.0272 (14)	0.0109 (12)	−0.0039 (11)	−0.0030 (10)	−0.0029 (10)
N3	0.0176 (12)	0.0201 (13)	0.0143 (12)	0.0003 (10)	−0.0068 (10)	−0.0023 (9)
N4	0.0139 (12)	0.0259 (14)	0.0124 (12)	−0.0017 (10)	−0.0028 (10)	−0.0037 (10)
C1	0.0170 (14)	0.0193 (15)	0.0181 (15)	−0.0068 (12)	−0.0055 (12)	−0.0032 (11)
C2	0.0171 (14)	0.0169 (14)	0.0193 (15)	−0.0039 (12)	−0.0073 (12)	−0.0029 (11)
C3	0.0180 (14)	0.0185 (15)	0.0204 (15)	−0.0068 (12)	−0.0061 (12)	−0.0042 (11)
C4	0.0213 (15)	0.0201 (15)	0.0214 (15)	0.0018 (13)	−0.0092 (13)	−0.0035 (12)
C5	0.0218 (15)	0.0171 (15)	0.0169 (14)	−0.0026 (12)	−0.0084 (12)	−0.0003 (11)
C6	0.0205 (15)	0.0197 (15)	0.0182 (15)	−0.0021 (12)	−0.0089 (12)	−0.0009 (11)
C7	0.0196 (15)	0.0262 (17)	0.0209 (15)	−0.0016 (13)	−0.0039 (13)	−0.0025 (12)
C8	0.0292 (17)	0.0239 (16)	0.0160 (15)	−0.0013 (14)	−0.0052 (13)	−0.0031 (12)
C9	0.0291 (17)	0.0260 (17)	0.0200 (16)	−0.0030 (14)	−0.0138 (14)	−0.0027 (12)
C10	0.0190 (15)	0.0256 (16)	0.0203 (15)	−0.0036 (13)	−0.0051 (13)	−0.0042 (12)
C11	0.0174 (14)	0.0127 (14)	0.0199 (15)	−0.0011 (11)	−0.0043 (12)	−0.0008 (11)
C12	0.0214 (16)	0.0186 (15)	0.0250 (16)	0.0014 (13)	−0.0078 (13)	−0.0024 (12)
C13	0.0191 (16)	0.0245 (17)	0.0317 (18)	0.0034 (13)	−0.0044 (14)	−0.0003 (13)
C14	0.0275 (17)	0.0178 (15)	0.0234 (16)	0.0069 (13)	0.0017 (14)	−0.0006 (12)
C15	0.0389 (19)	0.0198 (16)	0.0204 (16)	−0.0034 (14)	−0.0069 (14)	−0.0032 (12)
C16	0.0234 (16)	0.0168 (15)	0.0224 (15)	−0.0029 (13)	−0.0076 (13)	−0.0022 (12)
C17	0.0136 (14)	0.0215 (15)	0.0162 (14)	−0.0051 (12)	−0.0020 (12)	−0.0062 (11)
C18	0.0144 (14)	0.0210 (15)	0.0157 (14)	−0.0043 (12)	−0.0031 (12)	−0.0051 (11)
C19	0.0176 (14)	0.0172 (14)	0.0183 (14)	−0.0035 (12)	−0.0079 (12)	−0.0028 (11)
C20	0.0165 (14)	0.0287 (17)	0.0186 (15)	−0.0010 (13)	−0.0047 (12)	−0.0074 (12)
C21	0.0128 (13)	0.0242 (16)	0.0180 (14)	−0.0054 (12)	−0.0055 (12)	−0.0036 (12)
C22	0.0179 (14)	0.0215 (15)	0.0229 (15)	0.0003 (12)	−0.0064 (13)	−0.0066 (12)
C23	0.0235 (16)	0.0284 (17)	0.0247 (16)	−0.0013 (14)	−0.0110 (14)	0.0001 (13)
C24	0.0215 (15)	0.0346 (18)	0.0164 (15)	−0.0007 (14)	−0.0070 (13)	0.0001 (13)
C25	0.0181 (15)	0.0322 (18)	0.0204 (16)	0.0002 (13)	−0.0046 (13)	−0.0090 (13)
C26	0.0158 (14)	0.0228 (16)	0.0204 (15)	−0.0002 (12)	−0.0075 (12)	−0.0026 (12)
C27	0.0171 (14)	0.0110 (13)	0.0191 (14)	0.0062 (11)	−0.0094 (12)	−0.0040 (11)
C28	0.0185 (15)	0.0237 (16)	0.0174 (15)	−0.0062 (12)	−0.0042 (12)	−0.0029 (12)
C29	0.0187 (14)	0.0202 (15)	0.0246 (16)	0.0042 (12)	−0.0125 (13)	−0.0064 (12)
C30	0.0253 (16)	0.0236 (16)	0.0176 (15)	0.0063 (13)	−0.0104 (13)	−0.0049 (12)
C31	0.0197 (15)	0.0225 (16)	0.0174 (15)	−0.0019 (13)	−0.0013 (12)	−0.0030 (12)
C32	0.0154 (14)	0.0180 (15)	0.0195 (15)	0.0012 (12)	−0.0056 (12)	−0.0069 (11)
O1	0.0279 (12)	0.0592 (17)	0.0178 (12)	0.0029 (12)	−0.0119 (10)	0.0025 (11)
O2	0.0163 (11)	0.0369 (13)	0.0280 (12)	−0.0034 (10)	−0.0004 (10)	−0.0078 (10)
O3	0.0189 (11)	0.0466 (14)	0.0178 (11)	0.0030 (10)	−0.0080 (9)	−0.0040 (10)
N5	0.0200 (13)	0.0225 (13)	0.0163 (12)	−0.0038 (11)	−0.0059 (11)	−0.0063 (10)

Ag1—N1	2.141 (2)	C14—H14	0.9500
Ag1—N3	2.147 (2)	C15—C16	1.383 (4)
Ag1—O1i	2.768 (2)	C15—H15	0.9500
N1—N2	1.354 (3)	C16—H16	0.9500
N1—C1	1.354 (4)	C17—C18	1.405 (4)
N2—C3	1.356 (4)	C17—C21	1.492 (4)
N2—H2	0.8807	C18—C19	1.399 (4)
N3—C17	1.347 (4)	C18—C20	1.504 (4)
N3—N4	1.355 (3)	C19—C27	1.472 (4)
N4—C19	1.349 (4)	C20—H20A	0.9800
N4—H4	0.8804	C20—H20B	0.9800
C1—C2	1.411 (4)	C20—H20C	0.9800
C1—C5	1.483 (4)	C21—C22	1.397 (4)
C2—C3	1.396 (4)	C21—C26	1.401 (4)
C2—C4	1.495 (4)	C22—C23	1.379 (4)
C3—C11	1.469 (4)	C22—H22	0.9500
C4—H4A	0.9800	C23—C24	1.387 (4)
C4—H4B	0.9800	C23—H23	0.9500
C4—H4C	0.9800	C24—C25	1.383 (5)
C5—C6	1.397 (4)	C24—H24	0.9500
C5—C10	1.398 (4)	C25—C26	1.389 (4)
C6—C7	1.390 (4)	C25—H25	0.9500
C6—H6	0.9500	C26—H26	0.9500
C7—C8	1.389 (4)	C27—C32	1.396 (4)
C7—H7	0.9500	C27—C28	1.403 (4)
C8—C9	1.396 (4)	C28—C29	1.385 (4)
C8—H8	0.9500	C28—H28	0.9500
C9—C10	1.392 (4)	C29—C30	1.390 (4)
C9—H9	0.9500	C29—H29	0.9500
C10—H10	0.9500	C30—C31	1.384 (4)
C11—C12	1.402 (4)	C30—H30	0.9500
C11—C16	1.402 (4)	C31—C32	1.390 (4)
C12—C13	1.386 (4)	C31—H31	0.9500
C12—H12	0.9500	C32—H32	0.9500
C13—C14	1.385 (5)	O1—N5	1.259 (3)
C13—H13	0.9500	O2—N5	1.244 (3)
C14—C15	1.386 (5)	O3—N5	1.242 (3)
N1—Ag1—N3	167.23 (9)	C16—C15—H15	120.0
N2—N1—C1	105.1 (2)	C14—C15—H15	120.0
N2—N1—Ag1	115.79 (17)	C15—C16—C11	120.6 (3)
C1—N1—Ag1	137.10 (19)	C15—C16—H16	119.7
Ag1i—O1—N5	141.8 (2)	C11—C16—H16	119.7
N1—N2—C3	112.3 (2)	N3—C17—C18	110.9 (2)
N1—N2—H2	123.8	N3—C17—C21	118.8 (3)
C3—N2—H2	123.9	C18—C17—C21	130.2 (3)
C17—N3—N4	105.3 (2)	C19—C18—C17	104.7 (2)
C17—N3—Ag1	131.80 (19)	C19—C18—C20	127.4 (3)
N4—N3—Ag1	121.04 (17)	C17—C18—C20	127.8 (2)
C19—N4—N3	112.1 (2)	N4—C19—C18	106.9 (2)
C19—N4—H4	123.9	N4—C19—C27	121.2 (2)
N3—N4—H4	123.9	C18—C19—C27	132.0 (3)
N1—C1—C2	111.0 (2)	C18—C20—H20A	109.5
N1—C1—C5	120.1 (3)	C18—C20—H20B	109.5
C2—C1—C5	128.8 (3)	H20A—C20—H20B	109.5
C3—C2—C1	104.6 (3)	C18—C20—H20C	109.5
C3—C2—C4	128.0 (3)	H20A—C20—H20C	109.5
C1—C2—C4	127.1 (3)	H20B—C20—H20C	109.5
N2—C3—C2	107.0 (2)	C22—C21—C26	118.6 (3)
N2—C3—C11	119.9 (3)	C22—C21—C17	119.5 (3)
C2—C3—C11	133.0 (3)	C26—C21—C17	122.0 (3)
C2—C4—H4A	109.5	C23—C22—C21	120.6 (3)
C2—C4—H4B	109.5	C23—C22—H22	119.7
H4A—C4—H4B	109.5	C21—C22—H22	119.7
C2—C4—H4C	109.5	C22—C23—C24	120.8 (3)
H4A—C4—H4C	109.5	C22—C23—H23	119.6
H4B—C4—H4C	109.5	C24—C23—H23	119.6
C6—C5—C10	119.0 (3)	C25—C24—C23	119.1 (3)
C6—C5—C1	121.7 (3)	C25—C24—H24	120.5
C10—C5—C1	119.2 (3)	C23—C24—H24	120.5
C7—C6—C5	120.3 (3)	C24—C25—C26	120.9 (3)
C7—C6—H6	119.9	C24—C25—H25	119.6
C5—C6—H6	119.9	C26—C25—H25	119.6
C8—C7—C6	120.6 (3)	C25—C26—C21	120.0 (3)
C8—C7—H7	119.7	C25—C26—H26	120.0
C6—C7—H7	119.7	C21—C26—H26	120.0
C7—C8—C9	119.5 (3)	C32—C27—C28	118.5 (3)
C7—C8—H8	120.2	C32—C27—C19	120.4 (3)
C9—C8—H8	120.2	C28—C27—C19	121.1 (3)
C10—C9—C8	120.0 (3)	C29—C28—C27	120.5 (3)
C10—C9—H9	120.0	C29—C28—H28	119.8
C8—C9—H9	120.0	C27—C28—H28	119.8
C9—C10—C5	120.6 (3)	C28—C29—C30	120.4 (3)
C9—C10—H10	119.7	C28—C29—H29	119.8
C5—C10—H10	119.7	C30—C29—H29	119.8
C12—C11—C16	118.8 (3)	C31—C30—C29	119.5 (3)
C12—C11—C3	120.6 (3)	C31—C30—H30	120.2
C16—C11—C3	120.5 (3)	C29—C30—H30	120.2
C13—C12—C11	120.1 (3)	C30—C31—C32	120.4 (3)
C13—C12—H12	120.0	C30—C31—H31	119.8
C11—C12—H12	120.0	C32—C31—H31	119.8
C14—C13—C12	120.4 (3)	C31—C32—C27	120.7 (3)
C14—C13—H13	119.8	C31—C32—H32	119.7
C12—C13—H13	119.8	C27—C32—H32	119.7
C13—C14—C15	120.1 (3)	O3—N5—O2	121.6 (2)
C13—C14—H14	119.9	O3—N5—O1	118.2 (2)
C15—C14—H14	119.9	O2—N5—O1	120.2 (2)
C16—C15—C14	120.0 (3)
N3—Ag1—N1—N2	−20.6 (5)	C13—C14—C15—C16	0.7 (5)
N3—Ag1—N1—C1	140.4 (4)	C14—C15—C16—C11	−0.9 (4)
C1—N1—N2—C3	−0.5 (3)	C12—C11—C16—C15	0.9 (4)
Ag1—N1—N2—C3	166.22 (18)	C3—C11—C16—C15	−175.2 (3)
N1—Ag1—N3—C17	−161.4 (3)	N4—N3—C17—C18	−0.3 (3)
N1—Ag1—N3—N4	36.5 (5)	Ag1—N3—C17—C18	−164.46 (19)
C17—N3—N4—C19	0.8 (3)	N4—N3—C17—C21	−177.1 (2)
Ag1—N3—N4—C19	167.07 (18)	Ag1—N3—C17—C21	18.7 (4)
N2—N1—C1—C2	0.9 (3)	N3—C17—C18—C19	−0.3 (3)
Ag1—N1—C1—C2	−161.4 (2)	C21—C17—C18—C19	176.0 (3)
N2—N1—C1—C5	−175.0 (2)	N3—C17—C18—C20	179.7 (3)
Ag1—N1—C1—C5	22.7 (4)	C21—C17—C18—C20	−4.0 (5)
N1—C1—C2—C3	−1.0 (3)	N3—N4—C19—C18	−1.0 (3)
C5—C1—C2—C3	174.4 (3)	N3—N4—C19—C27	178.4 (2)
N1—C1—C2—C4	172.6 (3)	C17—C18—C19—N4	0.7 (3)
C5—C1—C2—C4	−11.9 (5)	C20—C18—C19—N4	−179.2 (3)
N1—N2—C3—C2	−0.1 (3)	C17—C18—C19—C27	−178.6 (3)
N1—N2—C3—C11	177.2 (2)	C20—C18—C19—C27	1.5 (5)
C1—C2—C3—N2	0.7 (3)	N3—C17—C21—C22	43.8 (4)
C4—C2—C3—N2	−172.9 (3)	C18—C17—C21—C22	−132.3 (3)
C1—C2—C3—C11	−176.2 (3)	N3—C17—C21—C26	−136.9 (3)
C4—C2—C3—C11	10.2 (5)	C18—C17—C21—C26	47.0 (4)
N1—C1—C5—C6	−38.9 (4)	C26—C21—C22—C23	−1.8 (4)
C2—C1—C5—C6	146.0 (3)	C17—C21—C22—C23	177.5 (3)
N1—C1—C5—C10	137.7 (3)	C21—C22—C23—C24	0.6 (5)
C2—C1—C5—C10	−37.4 (4)	C22—C23—C24—C25	1.0 (5)
C10—C5—C6—C7	−1.3 (4)	C23—C24—C25—C26	−1.4 (5)
C1—C5—C6—C7	175.3 (3)	C24—C25—C26—C21	0.2 (4)
C5—C6—C7—C8	0.9 (5)	C22—C21—C26—C25	1.4 (4)
C6—C7—C8—C9	0.2 (5)	C17—C21—C26—C25	−177.8 (3)
C7—C8—C9—C10	−0.8 (5)	N4—C19—C27—C32	34.1 (4)
C8—C9—C10—C5	0.4 (5)	C18—C19—C27—C32	−146.7 (3)
C6—C5—C10—C9	0.6 (4)	N4—C19—C27—C28	−145.0 (3)
C1—C5—C10—C9	−176.0 (3)	C18—C19—C27—C28	34.2 (5)
N2—C3—C11—C12	−149.9 (3)	C32—C27—C28—C29	−0.4 (4)
C2—C3—C11—C12	26.7 (5)	C19—C27—C28—C29	178.7 (3)
N2—C3—C11—C16	26.1 (4)	C27—C28—C29—C30	1.7 (4)
C2—C3—C11—C16	−157.3 (3)	C28—C29—C30—C31	−1.4 (4)
C16—C11—C12—C13	−0.6 (4)	C29—C30—C31—C32	−0.2 (4)
C3—C11—C12—C13	175.4 (3)	C30—C31—C32—C27	1.6 (4)
C11—C12—C13—C14	0.4 (5)	C28—C27—C32—C31	−1.2 (4)
C12—C13—C14—C15	−0.4 (5)	C19—C27—C32—C31	179.7 (3)

Cg1 and Cg2 are the centroids of the N3/N4/C17–C19 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.88	1.97	2.686 (3)	137
N4—H4···O3i	0.88	1.98	2.858 (3)	175
C26—H26···O3ii	0.95	2.58	3.358 (4)	140
C32—H32···O3i	0.95	2.50	3.145 (4)	125
C12—H12···Cg2iii	0.95	2.99	3.437 (4)	111
C30—H30···Cg3iv	0.95	2.98	3.456 (3)	112

Ag1—N1	2.141 (2)
Ag1—N3	2.147 (2)
Ag1—O1i	2.768 (2)

N1—Ag1—N3	167.23 (9)
N2—N1—C1	105.1 (2)
N2—N1—Ag1	115.79 (17)
C1—N1—Ag1	137.10 (19)
Ag1i—O1—N5	141.8 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N3/N4/C17–C19 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.88	1.97	2.686 (3)	137
N4—H4⋯O3i	0.88	1.98	2.858 (3)	175
C26—H26⋯O3ii	0.95	2.58	3.358 (4)	140
C32—H32⋯O3i	0.95	2.50	3.145 (4)	125
C12—H12⋯Cg2iii	0.95	2.99	3.437 (4)	111
C30—H30⋯Cg3iv	0.95	2.98	3.456 (3)	112

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .