catena-Poly[[bis­([mu]₂-4-methyl­benzo­ato-[kappa]²O:O')disilver(I)(Ag-Ag)]-[mu]₂-di-2-pyridylamine-[kappa]²N²:N^2'] and catena-poly[[(di-2-pyridylamine-[kappa]N²)([mu]₂-4-nitro­benzoato-[kappa]²O:O')disilver(I)(Ag-Ag)]-[mu]₃-4-nitro­benzoato-[kappa]³O:O':O']

Both title compounds are polynuclear polymeric complexes with binuclear units. In the former compound, [Ag₂(C₈H₇O₂)₂(C₁₀H₉N₃)]_n, the two Ag^I atoms display distorted square-planar coordinations. This compound contains a twofold axis and a crystallographic inversion centre, and di-2-pyridylamine (DPA) ligands crosslink adjacent binuclear units to form infinite polymeric chains. Crystal packing is stabilized by van der Waals inter­actions and partial [pi]-[pi] stacking inter­actions between the chains. The latter compound, [Ag₂(C₇H₄NO₄)₂(C₁₀H₉N₃)]_n, contains crystallographic inversion centres and the two Ag^I atoms exhibit two types of distorted square-pyramidal coordination. Ag-Ag argentophilic inter­actions and Ag-O crosslinking between adjacent binuclear units contribute to form infinite polymeric chains. Weak [pi]-[pi] stacking inter­actions are observed in the polymer chain. Crystal packing is stabilized by C-H...O hydrogen bonds and by weak [pi]-[pi] stacking inter­actions.

S1. Comment

Ag^I—N and Ag^I—O bonding complexes are potential bioinorganic materials (Clement & Jarrett, 1994; Russell & Hugo, 1994; Shaw, 1999; Feng et al., 2000; Gimeno & Laguna, 2004). Nomiya et al. (2004) reported that the dimeric or polymeric Ag^I—O bonding complexes show a wide range of antimicrobial activities. Kasuga et al. (2006) synthesized the polymeric light-stable and water-soluble Ag^I—O bonding complex, and demonstrated its antimicrobial activity against selected bacteria, yeasts and moulds. The aim of this study is to synthesize a new type of the antimicrobial Ag^I–benzoate complexe. Here, we report the crystal structures of the title polynuclear polymeric complexes with dinuclear units, the former being [C₂₆H₂₃N₃O₄Ag₂]_n, (I), made up of di-2-pyridylamine (DPA) and p-toluic acid (TA), with the electron-donating methyl group, and the latter being [C₂₄H₁₇N₅O₈Ag₂]_n, (II), comprised of DPA and p-nitrobenzoic acid (NA), with the electron-attracting nitro group.

The structure of (I) is shown to be a binuclear complex, which is composed of two Ag^I atoms, one DPA ligand and two TA ligands (Fig. 1). Selected geometric parameters are given in Table 1. The two halves of DPA are related by a twofold axis which passes through the central secondary amino group, N2—H22. Also, a crystallographic inversion centre is located at (1/2, 1/2, 1), i.e. at the centre of the Ag1—Ag1ⁱ bond vector [symmetry code: (i) 1 − x, 1 − y, 2 − z]. The Ag1 atom is coordinated by Ag1ⁱ, pyridyl atom N1 from DPA and carboxyl atoms O1 and O2 from two TAs. The Ag1—Ag1ⁱ distance (Table 1) is approximately equal to that of metallic silver (2.886 Å), indicating an apparent Ag—Ag metal bond (Zheng et al., 2003; Zhu et al., 2003; Tang et al., 2004; You et al., 2004). The chelating atoms form a distorted square-planar coordination geometry around Ag1 (r.m.s. deviation of fitted atoms = 0.1651 Å).

DPA crosslinks adjacent binuclear units to form infinite zigzag polymer chains along the c axis (Fig. 2), with the pyridine ring of DPA (C1–C5/N1) tilted from the coordination plane (Ag1/Ag1ⁱ/N1/O1/O2) by 17.2 (1)°, and with the two halves of DPA twisting about the central N2—H22 bond by 33.7 (1)°. In the polymer chain, bifurcated hydrogen bonds are present, namely N2—H22···O1 and N2—H22···O1ⁱⁱ [symmetry code: (ii) 1 - x, y, 3/2 − z] (Fig. 1, Table 2).

The crystal packing of (I) is stabilized by van der Waals interactions between the TAs of neighbouring polymer chains, with C9···C13ⁱⁱⁱ and C13···C9ⁱⁱⁱ of 3.541 (8) Å [symmetry code: (iii) 1/2 − x, 3/2 − y, 1 − z]. A partial π–π stacking interaction is also observed between adjacent parallel pyridine rings of DPA (Fig. 3, Table 3).

The structure of (II) is shown in Fig. 4, and selected geometric details are given in Table 4. The pyridine rings of DPA, C1–C5/N1 and C6–C10/N3, and the phenyl rings of NA, C12–C17 and C19–C24, are defined as rings A, B, C and D, respectively. As in (I), the unit complex in (II) is composed of two Ag^I atoms, one DPA ligand and two NA ligands, forming the binuclear complex. However, in (II), two types of slightly distorted square-pyramidal geometries are present. The Ag1 atom is coordinated by pyridyl atom N1 from DPA, carboxyl atoms O1 and O6 from two NAs and atom Ag2 in the basal plane (r.m.s. deviation of fitted atoms = 0.1804 Å), and the apical site of the pyramid is occupied by Ag2ⁱ [symmetry code: (i) 2 − x, −y, 1 − z]. However, the Ag2 atom is not coordinated by N. The Ag2 atom is coordinated by carboxyl atoms O2 and O5 from two NAs, atom O5ⁱⁱ from NA of an adjacent binuclear unit [symmetry code: (ii) 3 − x, −y, 1 − z] and atom Ag1 in the basal plane (r.m.s. deviation of fitted atoms = 0.1328 Å), and atom Ag1ⁱ occupies the apical site of the pyramid. There is an intramolecular N2—H22···O6 hydrogen bond (Fig. 4, Table 5).

The Ag1—Ag2 distance in the coordination basal plane (Table 4) indicates an apparent Ag—Ag metal bond. The axial Ag1—Ag2ⁱ (= Ag2—Ag1ⁱ) distance of the pyramids (Table 4) is shorter than the sum of the van der Waals radii of two Ag^I atoms (3.44 Å), and longer than the Ag—Ag metal bond. This may suggest that they are related by what has been referred to as argentophilicity (Kaltsoyannis, 1997; Tang et al., 2004). Argentophilic interactions crosslink two binuclear units along the axial direction of the pyramids, and Ag2—O5ⁱⁱ and O5—Ag2ⁱⁱ crosslink adjacent binclear units along the a axis. Consequently, the overall structure of (II) is formed into an infinite polymer chain complex along the a axis (Fig. 5). The A and B rings of DPA are tilted from each other by 16.7 (2)°, and two NAs are twisted at C11—C12 and C18—C19 by 29.6 (2) and by 10.5 (3)°, respectively, to avoid steric hindrance caused by polymerization. In the polymer chain of (II), crystallographic inversion centres are located at (1, 0, 1/2) and (1/2, 0, 1/2). Crystal packing is stablized by C—H···O interactions between polymer chains (Table 5). Weak π–π stacking interactions are observed between several adjacent six-membered rings, including rings C and D, an interaction which is along the axial direction of the coordination pyramid (Fig. 6, Table 6).

In the present study, two types of ligands are chosen, namely TA with the electron-donating methyl group and NA with the electron-attracting nitro group. Coordination geometries in both compounds are very similar, with Ag^I—O bond lengths ranging from 2.180 (3) to 2.214 (3) Å. In previously reported crystal structures of dimeric or polymeric Ag^I complexes containing benzoic acid or its derivatives as ligands, Ag^I—O bond lengths range from 2.175 to 2.302 Å (Usubaliev et al., 1981; Hedrich & Hartl, 1983; Smith et al., 1988; Movsumov et al., 1990; Mak et al., 1993; Smith et al., 1994; Ülkü et al., 1996; Jian et al., 2004; You et al., 2004; Wang & Okabe, 2005), which are comparable with those of the present complexes. This suggests that the coordination strengths of Ag^I—O bonds are unaffected by the properties of methyl and nitro substituents at the para position of benzoic acid.

S2. Experimental

All procedures were carried out at room temperature. For the synthesis of compound (I), AgNO₃ (2.5 mg, 0.015 mmol) dissolved in H₂O (0.1 ml) was added to di-2-pyridylamine (5 mg, 0.032 mmol) dissolved in dimethylformamide (DMF) (1 ml) and the mixture was stirred for 10 min. p-Toluic acid (3.9 mg, 0.029 mmol) dissolved in DMF (1 ml) was added to this solution and the mixture was stirred for 30 min. After evaporation for 10 d at room temperature, colourless platelet crystals were formed. For the synthesis of compound (II), AgNO₃ (1.25 mg, 0.008 mmol) dissolved in H₂O (0.1 ml) was added to di-2-pyridylamine (2.5 mg, 0.016 mmol) dissolved in MeOH–H₂O (90% v/v, 3 ml) and the mixture was stirred for 10 min. p-Nitrobenzoic acid (2.4 mg, 0.014 mmol) dissolved in DMF (1 ml) was added to this solution, and the mixture was stirred for 30 min. After evaporation for 5 d, colourless platelet crystals crystallized from the mixture.

S3. Refinement

For both compounds, all H atoms were located in difference Fourier maps and were then placed in ideal positions and treated as riding, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for aromatic H atoms, N—H = 0.86 Å and U_iso(H) = 1.2U_eq(N) for secondary amino H atoms, and C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms. For compound (I), the methyl H atoms were additionally allowed to rotate about the parent C—C bond. In compound (I), the highest maximum residual electron density is 0.62 Å from Ag1 and the deepest hole is 1.03 Å from Ag1. In compound (II), the corresponding values are 0.93 Å from Ag1 and 0.83 Å from Ag1, respectively.

Computing details

For both compounds, data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS (Betteridge et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.

Figures

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Unlabelled atoms are related to labelled atoms by the symmetry operation (i) for NA and (ii) for DPA. Dashed lines indicate the bifurcated hydrogen bond. [Symmetry codes: (i) 1 − x, 1 − y, 2 − z; (ii) 1 − x, y, 3/2 − z.]
	Fig. 2. A view of the core structure of (I), comprised of DPA, Ag1 and chelating atoms, showing the polymer chain along the c axis. H atoms have been omitted for clarity.
	Fig. 3. The crystal packing of the core structure of (I). Dashed lines indicate the partial π–π stacking interactions between the pyridine rings of DPA. H atoms have been omitted for clarity.
	Fig. 4. The molecular structure of (II), showing the atom-numbering scheme. Displacement ellipsoids are shown at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed line indicates the intramolecular hydrogen bond. [Symmetry codes: (i) 2 − x, −y, 1 − z; (ii) 3 − x, −y, 1 − z.]
	Fig. 5. The crystal packing of the core structure of (II), comprised of Ag1, Ag2 and the chelating atoms, showing the polymer chain along the a axis. [Symmetry code: (i) ? Please complete]
	Fig. 6. The crystal packing of (II). Dashed lines indicate weak π–π stacking interactions. H atoms have been omitted for clarity.

(I) catena-Poly[[bis(µ₂-4-methylbenzoato-κ²O:O')disilver(I)(Ag—Ag)]- µ₂-di-2-pyridylamine-κ²N²:N^2']

Crystal data

[Ag2(C8H7O2)2(C10H9N3)]	F(000) = 1304.00
Mr = 657.21	Dx = 1.859 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2yc	Cell parameters from 7596 reflections
a = 24.76 (2) Å	θ = 3.3–27.5°
b = 8.59 (1) Å	µ = 1.71 mm^−1
c = 11.55 (1) Å	T = 296 K
β = 107.11 (3)°	Platelet, colourless
V = 2348 (4) Å^3	0.20 × 0.10 × 0.03 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	1585 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.048
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −32→31
Tmin = 0.639, Tmax = 0.949	k = −11→11
11540 measured reflections	l = −14→14
2679 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0282P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.058	(Δ/σ)max = 0.001
S = 0.80	Δρmax = 0.54 e Å^−3
2679 reflections	Δρmin = −0.79 e Å^−3
160 parameters

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 using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Ag1	0.518213 (11)	0.64184 (3)	0.96130 (2)	0.04886 (10)
O1	0.44762 (9)	0.6062 (3)	0.79853 (19)	0.0485 (7)
O2	0.41382 (9)	0.4011 (3)	0.8695 (2)	0.0596 (8)
N1	0.54997 (10)	0.9039 (3)	0.9499 (2)	0.0301 (6)
N2	0.5000	0.9312 (4)	0.7500	0.0333 (8)
H22	0.5000	0.8311	0.7500	0.040*
C1	0.58397 (12)	0.9606 (4)	1.0539 (3)	0.0350 (8)
H1	0.5954	0.8936	1.1198	0.042*
C2	0.60309 (12)	1.1115 (4)	1.0692 (3)	0.0385 (8)
H2	0.6253	1.1473	1.1440	0.046*
C3	0.58802 (12)	1.2083 (4)	0.9688 (3)	0.0366 (8)
H3	0.6009	1.3106	0.9751	0.044*
C4	0.55416 (12)	1.1535 (4)	0.8603 (3)	0.0332 (7)
H4	0.5445	1.2168	0.7919	0.040*
C5	0.53449 (11)	1.0006 (4)	0.8544 (2)	0.0291 (7)
C6	0.41071 (12)	0.5059 (4)	0.7938 (3)	0.0332 (7)
C7	0.35821 (12)	0.5123 (4)	0.6887 (3)	0.0362 (8)
C8	0.35269 (14)	0.6147 (4)	0.5951 (3)	0.0529 (11)
H8	0.3817	0.6846	0.5982	0.063*
C9	0.30546 (16)	0.6164 (5)	0.4972 (3)	0.0680 (13)
H9	0.3036	0.6871	0.4352	0.082*
C10	0.26115 (14)	0.5189 (5)	0.4871 (3)	0.0561 (10)
C11	0.26599 (15)	0.4167 (6)	0.5823 (3)	0.0818 (16)
H11	0.2363	0.3493	0.5802	0.098*
C12	0.31385 (15)	0.4131 (5)	0.6799 (3)	0.0742 (15)
H12	0.3162	0.3415	0.7415	0.089*
C13	0.20958 (15)	0.5182 (6)	0.3768 (3)	0.0842 (15)
H13A	0.2028	0.6216	0.3441	0.126*
H13B	0.1773	0.4835	0.3996	0.126*
H13C	0.2159	0.4493	0.3167	0.126*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.04508 (15)	0.03957 (16)	0.04576 (15)	−0.01121 (15)	−0.01171 (11)	0.01155 (17)
O1	0.0429 (13)	0.0501 (19)	0.0411 (12)	−0.0140 (12)	−0.0055 (11)	0.0081 (12)
O2	0.0542 (15)	0.0517 (19)	0.0512 (14)	−0.0193 (12)	−0.0182 (12)	0.0260 (14)
N1	0.0299 (13)	0.0321 (16)	0.0243 (13)	0.0002 (11)	0.0015 (11)	0.0017 (11)
N2	0.044 (2)	0.023 (2)	0.0231 (18)	0.000	−0.0040 (17)	0.000
C1	0.0337 (16)	0.041 (2)	0.0246 (16)	0.0001 (15)	−0.0012 (14)	0.0045 (15)
C2	0.0383 (17)	0.044 (2)	0.0249 (16)	−0.0049 (15)	−0.0041 (14)	−0.0029 (15)
C3	0.0363 (17)	0.0345 (19)	0.0366 (19)	−0.0059 (15)	0.0068 (16)	−0.0028 (16)
C4	0.0374 (16)	0.0318 (19)	0.0284 (15)	0.0007 (15)	0.0065 (13)	0.0030 (16)
C5	0.0282 (15)	0.0329 (19)	0.0247 (16)	0.0032 (14)	0.0052 (13)	−0.0010 (14)
C6	0.0356 (17)	0.0294 (19)	0.0309 (17)	0.0033 (15)	0.0042 (15)	−0.0013 (15)
C7	0.0352 (17)	0.040 (2)	0.0309 (16)	0.0007 (15)	0.0054 (14)	0.0026 (16)
C8	0.043 (2)	0.062 (3)	0.045 (2)	−0.0141 (18)	0.0005 (17)	0.021 (2)
C9	0.065 (2)	0.079 (4)	0.043 (2)	−0.021 (2)	−0.0104 (19)	0.031 (2)
C10	0.044 (2)	0.074 (3)	0.0380 (19)	−0.008 (2)	−0.0071 (16)	0.014 (2)
C11	0.049 (2)	0.126 (5)	0.054 (2)	−0.039 (3)	−0.011 (2)	0.035 (3)
C12	0.054 (2)	0.104 (4)	0.047 (2)	−0.031 (2)	−0.0125 (19)	0.037 (2)
C13	0.062 (3)	0.110 (4)	0.056 (3)	−0.016 (3)	−0.021 (2)	0.025 (3)

Geometric parameters (Å, º)

Ag1—O1	2.179 (3)	C4—C5	1.396 (4)
Ag1—O2^i	2.203 (3)	C4—H4	0.9300
Ag1—N1	2.401 (4)	C6—C7	1.496 (4)
Ag1—Ag1^i	2.833 (3)	C7—C8	1.369 (4)
O1—C6	1.245 (4)	C7—C12	1.370 (5)
O2—C6	1.242 (4)	C8—C9	1.367 (5)
O2—Ag1^i	2.203 (3)	C8—H8	0.9300
N1—C1	1.339 (4)	C9—C10	1.358 (5)
N1—C5	1.344 (4)	C9—H9	0.9300
N2—C5	1.390 (3)	C10—C11	1.385 (5)
N2—C5^ii	1.390 (3)	C10—C13	1.515 (5)
N2—H22	0.8600	C11—C12	1.375 (5)
C1—C2	1.374 (5)	C11—H11	0.9300
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.386 (4)	C13—H13A	0.9600
C2—H2	0.9300	C13—H13B	0.9600
C3—C4	1.371 (4)	C13—H13C	0.9600
C3—H3	0.9300
O1—Ag1—O2^i	162.05 (9)	N2—C5—C4	124.2 (3)
O1—Ag1—N1	106.07 (9)	O2—C6—O1	125.3 (3)
O2^i—Ag1—N1	91.64 (9)	O2—C6—C7	117.2 (3)
O1—Ag1—Ag1^i	84.41 (8)	O1—C6—C7	117.5 (3)
O2^i—Ag1—Ag1^i	78.87 (7)	C8—C7—C12	116.7 (3)
N1—Ag1—Ag1^i	164.49 (6)	C8—C7—C6	121.7 (3)
C6—O1—Ag1	121.8 (2)	C12—C7—C6	121.6 (3)
C6—O2—Ag1^i	128.3 (2)	C9—C8—C7	121.5 (3)
C1—N1—C5	117.6 (3)	C9—C8—H8	119.3
C1—N1—Ag1	114.9 (2)	C7—C8—H8	119.3
C5—N1—Ag1	127.3 (2)	C10—C9—C8	122.5 (3)
C5—N2—C5^ii	129.2 (4)	C10—C9—H9	118.7
C5—N2—H22	115.4	C8—C9—H9	118.7
C5^ii—N2—H22	115.4	C9—C10—C11	116.3 (3)
N1—C1—C2	124.1 (3)	C9—C10—C13	122.3 (3)
N1—C1—H1	117.9	C11—C10—C13	121.3 (3)
C2—C1—H1	117.9	C12—C11—C10	121.2 (3)
C1—C2—C3	117.5 (3)	C12—C11—H11	119.4
C1—C2—H2	121.3	C10—C11—H11	119.4
C3—C2—H2	121.3	C7—C12—C11	121.7 (3)
C4—C3—C2	120.0 (3)	C7—C12—H12	119.2
C4—C3—H3	120.0	C11—C12—H12	119.2
C2—C3—H3	120.0	C10—C13—H13A	109.5
C3—C4—C5	118.6 (3)	C10—C13—H13B	109.5
C3—C4—H4	120.7	H13A—C13—H13B	109.5
C5—C4—H4	120.7	C10—C13—H13C	109.5
N1—C5—N2	113.7 (3)	H13A—C13—H13C	109.5
N1—C5—C4	122.0 (3)	H13B—C13—H13C	109.5
O2^i—Ag1—O1—C6	33.3 (4)	C3—C4—C5—N1	−3.3 (4)
N1—Ag1—O1—C6	−156.4 (2)	C3—C4—C5—N2	−179.9 (2)
Ag1^i—Ag1—O1—C6	12.0 (2)	Ag1^i—O2—C6—O1	2.3 (5)
O1—Ag1—N1—C1	164.85 (19)	Ag1^i—O2—C6—C7	−177.42 (19)
O2^i—Ag1—N1—C1	−18.1 (2)	Ag1—O1—C6—O2	−12.1 (5)
Ag1^i—Ag1—N1—C1	33.6 (4)	Ag1—O1—C6—C7	167.69 (18)
O1—Ag1—N1—C5	−10.5 (2)	O2—C6—C7—C8	−174.3 (3)
O2^i—Ag1—N1—C5	166.6 (2)	O1—C6—C7—C8	5.9 (5)
Ag1^i—Ag1—N1—C5	−141.71 (19)	O2—C6—C7—C12	4.0 (5)
C5—N1—C1—C2	1.2 (4)	O1—C6—C7—C12	−175.8 (3)
Ag1—N1—C1—C2	−174.6 (2)	C12—C7—C8—C9	−0.7 (6)
N1—C1—C2—C3	−2.9 (5)	C6—C7—C8—C9	177.7 (3)
C1—C2—C3—C4	1.5 (5)	C7—C8—C9—C10	0.7 (7)
C2—C3—C4—C5	1.4 (4)	C8—C9—C10—C11	0.4 (7)
C1—N1—C5—N2	179.0 (2)	C8—C9—C10—C13	−178.2 (4)
Ag1—N1—C5—N2	−5.8 (3)	C9—C10—C11—C12	−1.4 (7)
C1—N1—C5—C4	2.1 (4)	C13—C10—C11—C12	177.2 (4)
Ag1—N1—C5—C4	177.26 (19)	C8—C7—C12—C11	−0.4 (6)
C5^ii—N2—C5—N1	162.7 (2)	C6—C7—C12—C11	−178.8 (4)
C5^ii—N2—C5—C4	−20.4 (2)	C10—C11—C12—C7	1.5 (7)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H22···O1	0.86	2.48	3.197 (5)	141

(II) catena-poly[[(di-2-pyridylamine-κN²)(µ₂-4-nitrobenzoato- κ²O:O')disilver(I)(Ag—Ag)]-µ₃-4-nitrobenzoato-κ³O:O':O']

Crystal data

[Ag2(C7H4NO4)2(C10H9N3)]	Z = 2
Mr = 719.17	F(000) = 708.00
Triclinic, P1	Dx = 2.051 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.259 (8) Å	Cell parameters from 9330 reflections
b = 11.07 (1) Å	θ = 3.0–27.5°
c = 15.38 (2) Å	µ = 1.75 mm^−1
α = 82.66 (5)°	T = 296 K
β = 84.84 (4)°	Platelet, colourless
γ = 72.01 (4)°	0.40 × 0.20 × 0.03 mm
V = 1164 (2) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	4093 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.024
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.582, Tmax = 0.957	k = −14→14
11341 measured reflections	l = −19→19
5281 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0469P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.088	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 1.06 e Å^−3
5281 reflections	Δρmin = −0.79 e Å^−3
351 parameters

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 using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Ag1	0.89741 (3)	0.13823 (3)	0.554037 (15)	0.05584 (10)
Ag2	1.29267 (3)	−0.01184 (2)	0.571841 (14)	0.05205 (10)
O1	0.9050 (3)	0.0677 (2)	0.69404 (13)	0.0540 (6)
O2	1.1912 (3)	−0.0817 (2)	0.70066 (13)	0.0490 (5)
O3	0.9345 (4)	−0.2598 (3)	1.13020 (16)	0.0863 (9)
O4	0.6844 (3)	−0.0964 (2)	1.12742 (15)	0.0676 (7)
O5	1.3265 (3)	0.08205 (19)	0.43793 (12)	0.0427 (5)
O6	1.0217 (3)	0.2092 (2)	0.43068 (13)	0.0493 (5)
O7	1.2401 (5)	0.4777 (3)	0.02400 (18)	0.1043 (11)
O8	1.4476 (5)	0.3001 (3)	0.00161 (17)	0.0917 (10)
N1	0.5595 (3)	0.2341 (2)	0.55414 (16)	0.0407 (5)
N2	0.5637 (3)	0.3535 (2)	0.42195 (15)	0.0426 (6)
H22	0.6831	0.3072	0.4194	0.051*
N3	0.3472 (3)	0.5375 (2)	0.35207 (15)	0.0433 (6)
N4	0.8296 (4)	−0.1641 (2)	1.09215 (16)	0.0472 (6)
N5	1.3312 (4)	0.3697 (3)	0.04937 (17)	0.0574 (7)
C1	0.4695 (4)	0.2001 (3)	0.62935 (19)	0.0441 (7)
H1	0.5413	0.1356	0.6687	0.053*
C2	0.2773 (4)	0.2561 (3)	0.65051 (19)	0.0475 (7)
H2	0.2181	0.2296	0.7024	0.057*
C3	0.1754 (4)	0.3527 (3)	0.5923 (2)	0.0525 (8)
H3	0.0444	0.3927	0.6047	0.063*
C4	0.2648 (4)	0.3914 (3)	0.51573 (18)	0.0459 (7)
H4	0.1969	0.4582	0.4767	0.055*
C5	0.4599 (4)	0.3274 (3)	0.49845 (17)	0.0359 (6)
C6	0.3089 (5)	0.6192 (3)	0.2792 (2)	0.0499 (7)
H6	0.1960	0.6878	0.2804	0.060*
C7	0.4238 (5)	0.6094 (3)	0.20266 (19)	0.0508 (7)
H7	0.3899	0.6692	0.1540	0.061*
C8	0.5900 (5)	0.5084 (3)	0.2009 (2)	0.0523 (8)
H8	0.6720	0.4983	0.1505	0.063*
C9	0.6341 (4)	0.4227 (3)	0.27350 (19)	0.0478 (7)
H9	0.7456	0.3530	0.2731	0.057*
C10	0.5095 (4)	0.4410 (3)	0.34868 (17)	0.0370 (6)
C11	1.0307 (4)	−0.0220 (3)	0.73313 (17)	0.0353 (6)
C12	0.9801 (3)	−0.0591 (2)	0.82785 (16)	0.0333 (5)
C13	1.0915 (4)	−0.1698 (3)	0.87320 (17)	0.0389 (6)
H13	1.2011	−0.2211	0.8451	0.047*
C14	1.0430 (4)	−0.2057 (3)	0.95956 (18)	0.0414 (6)
H14	1.1178	−0.2807	0.9895	0.050*
C15	0.8808 (4)	−0.1273 (3)	1.00021 (16)	0.0364 (6)
C16	0.7681 (4)	−0.0156 (3)	0.95759 (18)	0.0391 (6)
H16	0.6607	0.0366	0.9865	0.047*
C17	0.8176 (4)	0.0174 (3)	0.87074 (18)	0.0395 (6)
H17	0.7412	0.0918	0.8408	0.047*
C18	1.1931 (4)	0.1674 (3)	0.40032 (17)	0.0364 (6)
C19	1.2366 (4)	0.2240 (2)	0.30983 (16)	0.0345 (6)
C20	1.1290 (4)	0.3465 (3)	0.27887 (18)	0.0416 (6)
H20	1.0358	0.3957	0.3161	0.050*
C21	1.1584 (4)	0.3964 (3)	0.19341 (19)	0.0448 (7)
H21	1.0860	0.4784	0.1725	0.054*
C22	1.2983 (4)	0.3209 (3)	0.14011 (17)	0.0392 (6)
C23	1.4094 (4)	0.1991 (3)	0.16914 (18)	0.0393 (6)
H23	1.5028	0.1502	0.1318	0.047*
C24	1.3787 (4)	0.1519 (3)	0.25430 (17)	0.0376 (6)
H24	1.4538	0.0706	0.2752	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.04425 (14)	0.07217 (19)	0.03662 (14)	−0.00622 (12)	0.00068 (11)	0.01681 (12)
Ag2	0.04241 (14)	0.06940 (18)	0.03360 (13)	−0.01001 (12)	0.00176 (10)	0.01413 (11)
O1	0.0465 (11)	0.0597 (13)	0.0356 (11)	0.0048 (10)	0.0002 (9)	0.0152 (10)
O2	0.0386 (10)	0.0592 (13)	0.0342 (10)	−0.0013 (9)	0.0040 (9)	0.0116 (9)
O3	0.0890 (18)	0.0873 (19)	0.0415 (13)	0.0163 (16)	0.0103 (13)	0.0261 (13)
O4	0.0669 (14)	0.0758 (16)	0.0398 (12)	−0.0013 (13)	0.0188 (12)	0.0025 (12)
O5	0.0412 (10)	0.0494 (11)	0.0282 (10)	−0.0041 (9)	0.0001 (8)	0.0043 (9)
O6	0.0367 (10)	0.0661 (14)	0.0341 (10)	−0.0069 (10)	−0.0007 (9)	0.0126 (10)
O7	0.149 (3)	0.0691 (18)	0.0549 (16)	0.008 (2)	0.0075 (19)	0.0292 (14)
O8	0.110 (2)	0.094 (2)	0.0452 (14)	−0.0104 (18)	0.0256 (16)	0.0150 (14)
N1	0.0362 (11)	0.0413 (12)	0.0380 (12)	−0.0072 (10)	−0.0027 (10)	0.0089 (10)
N2	0.0337 (11)	0.0474 (13)	0.0353 (12)	−0.0022 (10)	0.0001 (10)	0.0112 (11)
N3	0.0466 (13)	0.0377 (12)	0.0371 (13)	−0.0041 (11)	−0.0018 (11)	0.0045 (10)
N4	0.0499 (14)	0.0528 (15)	0.0324 (12)	−0.0106 (12)	0.0008 (11)	0.0051 (12)
N5	0.0720 (18)	0.0611 (17)	0.0359 (14)	−0.0224 (15)	−0.0010 (14)	0.0108 (13)
C1	0.0430 (15)	0.0439 (15)	0.0397 (15)	−0.0103 (13)	−0.0074 (13)	0.0131 (13)
C2	0.0492 (16)	0.0518 (17)	0.0342 (15)	−0.0098 (14)	0.0022 (13)	0.0050 (13)
C3	0.0441 (15)	0.0563 (18)	0.0413 (16)	0.0019 (14)	0.0055 (14)	0.0042 (14)
C4	0.0363 (13)	0.0521 (17)	0.0353 (15)	0.0031 (13)	−0.0047 (12)	0.0077 (13)
C5	0.0360 (13)	0.0389 (14)	0.0313 (13)	−0.0091 (11)	−0.0026 (11)	−0.0026 (11)
C6	0.0559 (17)	0.0386 (15)	0.0449 (17)	−0.0030 (14)	−0.0041 (15)	0.0060 (13)
C7	0.0666 (19)	0.0436 (16)	0.0354 (15)	−0.0117 (15)	−0.0037 (15)	0.0093 (13)
C8	0.0564 (18)	0.060 (2)	0.0344 (15)	−0.0141 (16)	0.0061 (14)	0.0020 (14)
C9	0.0428 (15)	0.0527 (18)	0.0385 (15)	−0.0045 (14)	0.0013 (13)	0.0031 (14)
C10	0.0388 (13)	0.0373 (14)	0.0340 (14)	−0.0124 (12)	−0.0054 (12)	0.0044 (11)
C11	0.0354 (13)	0.0387 (14)	0.0299 (13)	−0.0109 (11)	−0.0031 (11)	0.0031 (11)
C12	0.0320 (12)	0.0380 (14)	0.0285 (12)	−0.0109 (11)	−0.0031 (10)	0.0028 (11)
C13	0.0350 (13)	0.0413 (15)	0.0331 (14)	−0.0028 (12)	0.0000 (11)	0.0003 (12)
C14	0.0405 (14)	0.0390 (15)	0.0355 (14)	−0.0023 (12)	−0.0023 (12)	0.0060 (12)
C15	0.0403 (13)	0.0420 (14)	0.0252 (12)	−0.0116 (12)	0.0001 (11)	−0.0006 (11)
C16	0.0363 (13)	0.0399 (14)	0.0346 (14)	−0.0035 (12)	0.0023 (12)	−0.0027 (12)
C17	0.0378 (13)	0.0385 (14)	0.0358 (14)	−0.0042 (12)	−0.0067 (12)	0.0054 (12)
C18	0.0404 (14)	0.0409 (14)	0.0279 (13)	−0.0135 (12)	−0.0034 (11)	0.0010 (11)
C19	0.0368 (13)	0.0383 (14)	0.0284 (13)	−0.0125 (11)	−0.0030 (11)	0.0010 (11)
C20	0.0418 (14)	0.0437 (15)	0.0347 (14)	−0.0079 (12)	0.0000 (12)	−0.0014 (12)
C21	0.0501 (16)	0.0377 (15)	0.0419 (16)	−0.0088 (13)	−0.0080 (13)	0.0055 (13)
C22	0.0472 (15)	0.0432 (15)	0.0278 (13)	−0.0181 (13)	−0.0016 (12)	0.0051 (12)
C23	0.0366 (13)	0.0437 (15)	0.0340 (14)	−0.0094 (12)	0.0028 (12)	−0.0011 (12)
C24	0.0368 (13)	0.0401 (14)	0.0328 (13)	−0.0094 (12)	−0.0021 (11)	0.0025 (12)

Geometric parameters (Å, º)

Ag1—O6	2.187 (3)	C4—H4	0.9300
Ag1—O1	2.194 (3)	C6—C7	1.376 (4)
Ag1—N1	2.353 (3)	C6—H6	0.9300
Ag1—Ag2	2.855 (3)	C7—C8	1.370 (5)
Ag1—Ag2^i	3.158 (2)	C7—H7	0.9300
Ag2—O2	2.183 (3)	C8—C9	1.362 (4)
Ag2—O5	2.214 (3)	C8—H8	0.9300
Ag2—O5^ii	2.626 (4)	C9—C10	1.398 (4)
O1—C11	1.252 (3)	C9—H9	0.9300
O2—C11	1.244 (3)	C11—C12	1.507 (4)
O3—N4	1.212 (4)	C12—C13	1.384 (4)
O4—N4	1.217 (3)	C12—C17	1.389 (4)
O5—C18	1.249 (3)	C13—C14	1.383 (4)
O6—C18	1.256 (3)	C13—H13	0.9300
O7—N5	1.207 (4)	C14—C15	1.381 (4)
O8—N5	1.216 (3)	C14—H14	0.9300
N1—C5	1.322 (4)	C15—C16	1.375 (4)
N1—C1	1.346 (4)	C16—C17	1.385 (4)
N2—C5	1.387 (4)	C16—H16	0.9300
N2—C10	1.389 (4)	C17—H17	0.9300
N2—H22	0.8600	C18—C19	1.500 (4)
N3—C10	1.326 (4)	C19—C20	1.386 (4)
N3—C6	1.339 (4)	C19—C24	1.392 (4)
N4—C15	1.468 (4)	C20—C21	1.384 (4)
N5—C22	1.457 (4)	C20—H20	0.9300
C1—C2	1.368 (4)	C21—C22	1.379 (4)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.370 (5)	C22—C23	1.381 (4)
C2—H2	0.9300	C23—C24	1.372 (4)
C3—C4	1.378 (4)	C23—H23	0.9300
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.392 (4)
O6—Ag1—O1	153.23 (9)	C8—C7—C6	117.5 (3)
O6—Ag1—N1	107.18 (10)	C8—C7—H7	121.3
O1—Ag1—N1	95.94 (9)	C6—C7—H7	121.3
O6—Ag1—Ag2	81.16 (9)	C9—C8—C7	119.4 (3)
O1—Ag1—Ag2	77.11 (7)	C9—C8—H8	120.3
N1—Ag1—Ag2	170.57 (6)	C7—C8—H8	120.3
O6—Ag1—Ag2^i	83.11 (10)	C8—C9—C10	119.1 (3)
O1—Ag1—Ag2^i	118.55 (9)	C8—C9—H9	120.4
N1—Ag1—Ag2^i	68.95 (9)	C10—C9—H9	120.4
Ag2—Ag1—Ag2^i	108.55 (7)	N3—C10—N2	120.3 (2)
O2—Ag2—O5	167.26 (8)	N3—C10—C9	122.7 (3)
O2—Ag2—Ag1	84.96 (8)	N2—C10—C9	117.0 (2)
O5—Ag2—Ag1	82.33 (8)	O2—C11—O1	125.8 (3)
O2—Ag2—Ag1^i	101.48 (10)	O2—C11—C12	118.2 (3)
O5—Ag2—Ag1^i	73.65 (10)	O1—C11—C12	116.1 (2)
Ag1—Ag2—Ag1^i	71.45 (7)	C13—C12—C17	118.9 (3)
O2—Ag2—O5^ii	109.31 (9)	C13—C12—C11	121.1 (2)
O5—Ag2—O5^ii	83.30 (9)	C17—C12—C11	120.0 (3)
Ag1—Ag2—O5^ii	161.49 (5)	C14—C13—C12	121.3 (2)
C11—O1—Ag1	129.04 (18)	C14—C13—H13	119.4
C11—O2—Ag2	119.62 (19)	C12—C13—H13	119.4
C18—O5—Ag2	123.78 (18)	C15—C14—C13	118.3 (3)
C18—O6—Ag1	126.5 (2)	C15—C14—H14	120.8
C5—N1—C1	119.0 (2)	C13—C14—H14	120.8
C5—N1—Ag1	128.15 (19)	C16—C15—C14	122.0 (3)
C1—N1—Ag1	111.83 (19)	C16—C15—N4	119.4 (2)
C5—N2—C10	131.6 (2)	C14—C15—N4	118.6 (3)
C5—N2—H22	114.2	C15—C16—C17	118.7 (2)
C10—N2—H22	114.2	C15—C16—H16	120.7
C10—N3—C6	116.3 (2)	C17—C16—H16	120.7
O3—N4—O4	122.6 (3)	C16—C17—C12	120.8 (3)
O3—N4—C15	118.8 (2)	C16—C17—H17	119.6
O4—N4—C15	118.5 (3)	C12—C17—H17	119.6
O7—N5—O8	122.3 (3)	O5—C18—O6	125.8 (3)
O7—N5—C22	118.7 (3)	O5—C18—C19	118.3 (2)
O8—N5—C22	119.0 (3)	O6—C18—C19	115.9 (3)
N1—C1—C2	123.0 (3)	C20—C19—C24	119.1 (3)
N1—C1—H1	118.5	C20—C19—C18	120.4 (2)
C2—C1—H1	118.5	C24—C19—C18	120.4 (3)
C1—C2—C3	117.5 (3)	C21—C20—C19	120.9 (2)
C1—C2—H2	121.2	C21—C20—H20	119.5
C3—C2—H2	121.2	C19—C20—H20	119.5
C2—C3—C4	120.7 (3)	C22—C21—C20	118.0 (3)
C2—C3—H3	119.6	C22—C21—H21	121.0
C4—C3—H3	119.6	C20—C21—H21	121.0
C3—C4—C5	118.0 (3)	C21—C22—C23	122.5 (3)
C3—C4—H4	121.0	C21—C22—N5	119.5 (3)
C5—C4—H4	121.0	C23—C22—N5	118.0 (2)
N1—C5—N2	114.8 (2)	C24—C23—C22	118.5 (2)
N1—C5—C4	121.7 (3)	C24—C23—H23	120.8
N2—C5—C4	123.5 (3)	C22—C23—H23	120.8
N3—C6—C7	125.0 (3)	C23—C24—C19	120.9 (3)
N3—C6—H6	117.5	C23—C24—H24	119.6
C7—C6—H6	117.5	C19—C24—H24	119.6
O6—Ag1—Ag2—O2	176.48 (8)	C5—N2—C10—N3	16.2 (5)
O1—Ag1—Ag2—O2	12.22 (9)	C5—N2—C10—C9	−164.7 (3)
Ag2^i—Ag1—Ag2—O2	−103.90 (10)	C8—C9—C10—N3	1.1 (5)
O6—Ag1—Ag2—O5	−4.36 (8)	C8—C9—C10—N2	−178.0 (3)
O1—Ag1—Ag2—O5	−168.62 (8)	Ag2—O2—C11—O1	10.3 (4)
Ag2^i—Ag1—Ag2—O5	75.26 (10)	Ag2—O2—C11—C12	−169.59 (17)
O6—Ag1—Ag2—Ag1^i	−79.62 (11)	Ag1—O1—C11—O2	8.5 (4)
O1—Ag1—Ag2—Ag1^i	116.12 (10)	Ag1—O1—C11—C12	−171.60 (17)
Ag2^i—Ag1—Ag2—Ag1^i	0.0	O2—C11—C12—C13	−11.4 (4)
O6—Ag1—O1—C11	−52.7 (4)	O1—C11—C12—C13	168.8 (3)
N1—Ag1—O1—C11	157.3 (3)	O2—C11—C12—C17	169.6 (3)
Ag2—Ag1—O1—C11	−16.2 (2)	O1—C11—C12—C17	−10.3 (4)
Ag2^i—Ag1—O1—C11	88.1 (3)	C17—C12—C13—C14	0.6 (4)
O5—Ag2—O2—C11	−20.2 (5)	C11—C12—C13—C14	−178.5 (2)
Ag1—Ag2—O2—C11	−16.5 (2)	C12—C13—C14—C15	−0.7 (4)
Ag1^i—Ag2—O2—C11	−86.3 (2)	C13—C14—C15—C16	−0.2 (4)
O2—Ag2—O5—C18	9.2 (5)	C13—C14—C15—N4	−179.4 (2)
Ag1—Ag2—O5—C18	5.4 (2)	O3—N4—C15—C16	−176.9 (3)
Ag1^i—Ag2—O5—C18	78.2 (2)	O4—N4—C15—C16	2.3 (4)
O1—Ag1—O6—C18	42.3 (3)	O3—N4—C15—C14	2.3 (4)
N1—Ag1—O6—C18	−169.1 (2)	O4—N4—C15—C14	−178.5 (3)
Ag2—Ag1—O6—C18	6.4 (2)	C14—C15—C16—C17	1.2 (4)
Ag2^i—Ag1—O6—C18	−103.7 (2)	N4—C15—C16—C17	−179.7 (2)
O6—Ag1—N1—C5	−9.4 (3)	C15—C16—C17—C12	−1.3 (4)
O1—Ag1—N1—C5	157.0 (2)	C13—C12—C17—C16	0.4 (4)
Ag2^i—Ag1—N1—C5	−84.7 (2)	C11—C12—C17—C16	179.5 (2)
O6—Ag1—N1—C1	−177.63 (19)	Ag2—O5—C18—O6	−2.4 (4)
O1—Ag1—N1—C1	−11.3 (2)	Ag2—O5—C18—C19	179.29 (16)
Ag2^i—Ag1—N1—C1	107.1 (2)	Ag1—O6—C18—O5	−4.4 (4)
C5—N1—C1—C2	1.4 (4)	Ag1—O6—C18—C19	173.95 (17)
Ag1—N1—C1—C2	170.8 (2)	O5—C18—C19—C20	−154.6 (3)
N1—C1—C2—C3	−1.3 (5)	O6—C18—C19—C20	27.0 (4)
C1—C2—C3—C4	−0.1 (5)	O5—C18—C19—C24	28.8 (4)
C2—C3—C4—C5	1.4 (5)	O6—C18—C19—C24	−149.7 (3)
C1—N1—C5—N2	−178.5 (2)	C24—C19—C20—C21	1.4 (4)
Ag1—N1—C5—N2	13.9 (4)	C18—C19—C20—C21	−175.4 (3)
C1—N1—C5—C4	0.1 (4)	C19—C20—C21—C22	−0.2 (4)
Ag1—N1—C5—C4	−167.45 (19)	C20—C21—C22—C23	−0.5 (4)
C10—N2—C5—N1	178.6 (3)	C20—C21—C22—N5	179.1 (3)
C10—N2—C5—C4	0.0 (5)	O7—N5—C22—C21	3.0 (5)
C3—C4—C5—N1	−1.4 (4)	O8—N5—C22—C21	−176.2 (3)
C3—C4—C5—N2	177.0 (3)	O7—N5—C22—C23	−177.4 (3)
C10—N3—C6—C7	0.3 (5)	O8—N5—C22—C23	3.4 (4)
N3—C6—C7—C8	0.0 (5)	C21—C22—C23—C24	0.0 (4)
C6—C7—C8—C9	0.2 (5)	N5—C22—C23—C24	−179.6 (3)
C7—C8—C9—C10	−0.8 (5)	C22—C23—C24—C19	1.2 (4)
C6—N3—C10—N2	178.2 (3)	C20—C19—C24—C23	−1.8 (4)
C6—N3—C10—C9	−0.9 (4)	C18—C19—C24—C23	174.9 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H22···O6	0.86	2.37	3.220 (5)	168
C6—H6···O1^iii	0.93	2.65	3.394 (5)	138
C7—H7···O8^iv	0.93	2.60	3.316 (5)	134
C14—H14···O7^v	0.93	2.55	3.404 (6)	154
C23—H23···O4^vi	0.93	2.65	3.372 (5)	135

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