Bis(1,10-phenanthroline-5,6-dione-κN,N')silver(I) 2-hy-droxy-3,5-dinitro-benzoate.

In the cation of the title salt, [Ag(C(12)H(6)N(2)O(2))(2)](C(7)H(3)N(2)O(7)), the Ag(I) atom is coordinated in a distorted tetra-hedral geometry by four N atoms from two 1,10-phenanthroline-5,6-dione ligands, while the 3,5-dinitro-salicylate anion has only a short contact [2.847 (6) Å] between one of its O atoms and the Ag(I) atom. The dihedral angle between the two 1,10-phenanthroline-5,6-dione ligands is 58.4 (1)°. There is an intra-molecular O-H⋯O hydrogen bond in the 3,5-dinitro-salicylate anion.

Related literature

For general background to the structures and potential applications of supra­molecular architectures with 1,10-phenantroline-5,6-dione and 3,5-dinitro­salicylic acid, see: Hiort et al. (1993 ▶); Song et al. (2007 ▶); Che et al. (2008 ▶); Onuegbu et al. (2009 ▶). For the synthesis of the 1,10-phenantroline-5,6-dione ligand, see: Dickeson & Sumers (1970 ▶).

Experimental

Crystal data

[Ag(C12H6N2O2)2](C7H3N2O7)

M = 755.36

Monoclinic,

a = 11.757 (2) Å

b = 18.297 (4) Å

c = 13.223 (3) Å

β = 103.91 (3)°

V = 2761.1 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.81 mm−1

T = 174 K

0.30 × 0.24 × 0.20 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.780, T max = 0.910

12726 measured reflections

5059 independent reflections

3914 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.163

S = 1.11

5013 reflections

442 parameters

22 restraints

H-atom parameters constrained

Δρmax = 1.11 e Å−3

Δρmin = −0.72 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053785/vn2025sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053785/vn2025Isup2.hkl

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

C24H12AgN4O4·C7H3N2O7	F(000) = 1512
Mr = 755.36	Dx = 1.817 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5197 reflections
a = 11.757 (2) Å	θ = 3.2–25.4°
b = 18.297 (4) Å	µ = 0.81 mm−1
c = 13.223 (3) Å	T = 174 K
β = 103.91 (3)°	Prism, yellow
V = 2761.1 (11) Å3	0.3 × 0.24 × 0.2 mm
Z = 4

Oxford Diffraction Gemini R Ultra diffractometer	5059 independent reflections
Radiation source: fine-focus sealed tube	3914 reflections with I > 2σ(I)
graphite	Rint = 0.052
ω scans	θmax = 25.4°, θmin = 3.2°
Absorption correction: multi-scan SADABS (Bruker, 2002)	h = −14→11
Tmin = 0.780, Tmax = 0.910	k = −17→22
12726 measured reflections	l = −15→13

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0354P)2 + 13.4705P] where P = (Fo2 + 2Fc2)/3
5013 reflections	(Δ/σ)max < 0.001
442 parameters	Δρmax = 1.11 e Å−3
22 restraints	Δρmin = −0.72 e Å−3

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. 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 > 2sigma(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	0.21081 (6)	0.44038 (3)	0.52487 (5)	0.0540 (2)
C1	0.4793 (7)	0.5137 (4)	0.6222 (5)	0.0435 (18)
H1	0.4399	0.5580	0.6074	0.052*
C2	0.5976 (7)	0.5157 (4)	0.6690 (6)	0.048 (2)
H2	0.6371	0.5599	0.6845	0.058*
C3	0.6552 (7)	0.4497 (4)	0.6920 (6)	0.0470 (19)
H3	0.7345	0.4488	0.7248	0.056*
C4	0.5941 (6)	0.3844 (4)	0.6659 (5)	0.0380 (16)
C5	0.6515 (9)	0.3155 (4)	0.6883 (7)	0.062 (2)
C6	0.5895 (7)	0.2505 (5)	0.6710 (7)	0.063 (2)
C7	0.4678 (6)	0.2544 (4)	0.6244 (5)	0.0431 (18)
C8	0.3994 (8)	0.1885 (4)	0.6037 (6)	0.053 (2)
H8	0.4340	0.1433	0.6229	0.064*
C9	0.2836 (9)	0.1930 (5)	0.5557 (7)	0.063 (2)
H9	0.2388	0.1508	0.5403	0.075*
C10	0.2342 (7)	0.2594 (5)	0.5305 (7)	0.055 (2)
H10	0.1552	0.2613	0.4966	0.066*
C11	0.4090 (6)	0.3201 (3)	0.5978 (5)	0.0338 (16)
C12	0.4738 (5)	0.3869 (3)	0.6196 (5)	0.0335 (16)
C13	0.0848 (7)	0.4147 (4)	0.2775 (7)	0.055 (2)
H13	0.1080	0.3666	0.2933	0.066*
C14	0.0374 (8)	0.4324 (5)	0.1743 (7)	0.061 (2)
H14	0.0287	0.3972	0.1223	0.073*
C15	0.0034 (7)	0.5036 (5)	0.1506 (6)	0.053 (2)
H15	−0.0298	0.5170	0.0820	0.064*
C16	0.0190 (6)	0.5564 (4)	0.2312 (5)	0.0432 (18)
C17	−0.0122 (5)	0.6312 (4)	0.2098 (5)	0.052 (2)
C18	−0.0077 (7)	0.6805 (4)	0.2948 (6)	0.055 (2)
C19	0.0460 (6)	0.6571 (4)	0.3993 (6)	0.0447 (18)
C20	0.0688 (7)	0.7058 (4)	0.4853 (7)	0.055 (2)
H20	0.0483	0.7548	0.4749	0.067*
C21	0.1205 (8)	0.6816 (5)	0.5829 (7)	0.059 (2)
H21	0.1348	0.7131	0.6398	0.071*
C22	0.1506 (7)	0.6090 (5)	0.5945 (6)	0.056 (2)
H22	0.1865	0.5925	0.6611	0.067*
C23	0.0809 (6)	0.5844 (3)	0.4175 (5)	0.0369 (16)
C24	0.0632 (5)	0.5330 (3)	0.3334 (5)	0.0322 (15)
C25	0.6149 (7)	0.4146 (4)	0.9278 (5)	0.0419 (18)
C26	0.5083 (7)	0.4530 (4)	0.8867 (5)	0.0411 (18)
C27	0.4075 (6)	0.4103 (4)	0.8430 (5)	0.0388 (17)
C28	0.4092 (7)	0.3351 (4)	0.8460 (5)	0.0433 (18)
H28	0.3421	0.3080	0.8181	0.052*
C29	0.5165 (8)	0.3002 (4)	0.8928 (5)	0.0434 (19)
C30	0.6177 (7)	0.3387 (4)	0.9327 (6)	0.0435 (18)
H30	0.6871	0.3143	0.9625	0.052*
C31	0.2956 (8)	0.4467 (5)	0.7881 (6)	0.050 (2)
N1	0.4178 (5)	0.4524 (3)	0.5970 (4)	0.0347 (13)
N2	0.2931 (5)	0.3228 (3)	0.5518 (5)	0.0399 (14)
N3	0.0992 (5)	0.4629 (3)	0.3562 (5)	0.0422 (15)
N4	0.1319 (5)	0.5605 (3)	0.5164 (5)	0.0423 (14)
N5	0.7268 (7)	0.4516 (5)	0.9629 (5)	0.0587 (19)
N6	0.5177 (8)	0.2213 (4)	0.9005 (5)	0.0560 (19)
O1	0.7645 (7)	0.3121 (4)	0.7270 (6)	0.088 (2)
O2	0.6419 (7)	0.1890 (4)	0.6988 (6)	0.096 (2)
O3	−0.0430 (5)	0.6542 (3)	0.1162 (4)	0.0700 (18)
O4	−0.0502 (6)	0.7445 (3)	0.2780 (5)	0.080 (2)
O5	0.8165 (6)	0.4147 (4)	0.9745 (6)	0.091 (2)
O6	0.7295 (6)	0.5175 (4)	0.9763 (6)	0.085 (2)
O7	0.5032 (6)	0.5236 (3)	0.8852 (4)	0.0608 (16)
H7	0.4365	0.5366	0.8565	0.091*
O8	0.2947 (6)	0.5172 (3)	0.7949 (5)	0.0684 (17)
O9	0.2133 (5)	0.4109 (4)	0.7368 (5)	0.0641 (16)
O10	0.4296 (7)	0.1876 (3)	0.8584 (5)	0.0713 (19)
O11	0.6097 (6)	0.1916 (3)	0.9511 (5)	0.0684 (18)

	U11	U22	U33	U12	U13	U23
Ag1	0.0472 (4)	0.0491 (4)	0.0609 (4)	0.0150 (3)	0.0036 (3)	0.0149 (3)
C1	0.056 (5)	0.038 (4)	0.039 (4)	−0.007 (4)	0.015 (4)	0.001 (3)
C2	0.054 (5)	0.046 (5)	0.048 (5)	−0.011 (4)	0.019 (4)	−0.001 (4)
C3	0.033 (4)	0.065 (6)	0.042 (4)	−0.003 (4)	0.008 (3)	−0.006 (4)
C4	0.036 (4)	0.043 (4)	0.037 (4)	0.007 (3)	0.013 (3)	0.001 (3)
C5	0.084 (7)	0.059 (5)	0.049 (5)	0.022 (5)	0.028 (5)	0.008 (4)
C6	0.067 (5)	0.068 (6)	0.057 (5)	0.007 (5)	0.019 (4)	−0.001 (5)
C7	0.056 (4)	0.045 (4)	0.033 (4)	0.005 (4)	0.020 (3)	0.001 (3)
C8	0.085 (5)	0.031 (4)	0.049 (5)	0.014 (4)	0.026 (4)	0.008 (4)
C9	0.077 (5)	0.053 (5)	0.064 (6)	−0.012 (5)	0.027 (4)	−0.010 (5)
C10	0.043 (5)	0.050 (5)	0.072 (6)	−0.002 (4)	0.014 (4)	−0.009 (4)
C11	0.044 (4)	0.027 (4)	0.031 (4)	0.008 (3)	0.011 (3)	0.001 (3)
C12	0.041 (4)	0.031 (4)	0.030 (4)	−0.001 (3)	0.011 (3)	0.002 (3)
C13	0.051 (5)	0.036 (4)	0.072 (6)	−0.001 (4)	0.005 (4)	−0.002 (4)
C14	0.056 (6)	0.057 (6)	0.063 (6)	−0.002 (4)	0.002 (4)	−0.024 (5)
C15	0.047 (5)	0.060 (6)	0.047 (5)	−0.001 (4)	0.003 (4)	−0.002 (4)
C16	0.032 (4)	0.042 (4)	0.053 (5)	0.000 (3)	0.006 (3)	0.004 (4)
C17	0.041 (5)	0.053 (5)	0.058 (5)	0.003 (4)	0.002 (4)	0.019 (4)
C18	0.041 (5)	0.049 (5)	0.071 (6)	−0.004 (4)	0.004 (4)	0.006 (5)
C19	0.038 (4)	0.037 (4)	0.058 (5)	0.001 (3)	0.008 (4)	0.001 (4)
C20	0.045 (5)	0.035 (4)	0.084 (7)	0.001 (4)	0.012 (5)	−0.008 (4)
C21	0.052 (5)	0.055 (5)	0.069 (6)	0.003 (4)	0.012 (5)	−0.017 (5)
C22	0.047 (5)	0.070 (6)	0.047 (5)	−0.002 (4)	0.004 (4)	−0.005 (4)
C23	0.028 (4)	0.036 (4)	0.045 (4)	0.003 (3)	0.005 (3)	0.002 (3)
C24	0.022 (3)	0.029 (4)	0.045 (4)	0.000 (3)	0.006 (3)	0.004 (3)
C25	0.056 (5)	0.040 (4)	0.029 (4)	−0.010 (4)	0.008 (3)	−0.003 (3)
C26	0.061 (5)	0.033 (4)	0.033 (4)	0.001 (4)	0.018 (4)	−0.003 (3)
C27	0.045 (5)	0.039 (4)	0.035 (4)	0.001 (3)	0.016 (3)	0.003 (3)
C28	0.061 (5)	0.042 (4)	0.032 (4)	−0.008 (4)	0.019 (4)	−0.002 (3)
C29	0.071 (6)	0.030 (4)	0.035 (4)	0.006 (4)	0.024 (4)	0.006 (3)
C30	0.047 (5)	0.046 (5)	0.038 (4)	0.004 (4)	0.013 (3)	0.004 (3)
C31	0.060 (6)	0.049 (5)	0.048 (5)	0.014 (4)	0.024 (4)	0.011 (4)
N1	0.036 (3)	0.032 (3)	0.035 (3)	0.002 (3)	0.008 (3)	0.000 (3)
N2	0.038 (4)	0.037 (3)	0.045 (3)	0.000 (3)	0.009 (3)	−0.001 (3)
N3	0.038 (4)	0.032 (3)	0.053 (4)	0.000 (3)	0.004 (3)	−0.002 (3)
N4	0.037 (3)	0.043 (4)	0.046 (4)	0.003 (3)	0.007 (3)	0.006 (3)
N5	0.059 (5)	0.071 (6)	0.042 (4)	−0.011 (4)	0.006 (3)	−0.007 (4)
N6	0.091 (6)	0.039 (4)	0.046 (4)	0.003 (4)	0.032 (4)	0.003 (3)
O1	0.081 (5)	0.099 (6)	0.084 (5)	0.033 (4)	0.020 (4)	0.021 (4)
O2	0.086 (6)	0.079 (5)	0.110 (6)	0.022 (4)	−0.003 (4)	0.000 (4)
O3	0.067 (4)	0.071 (4)	0.067 (4)	0.003 (3)	0.005 (3)	0.024 (3)
O4	0.097 (5)	0.040 (4)	0.094 (5)	0.018 (3)	0.005 (4)	0.016 (3)
O5	0.055 (5)	0.099 (6)	0.113 (6)	−0.004 (4)	0.008 (4)	−0.033 (5)
O6	0.089 (5)	0.050 (4)	0.098 (5)	−0.024 (4)	−0.016 (4)	0.002 (4)
O7	0.086 (5)	0.039 (3)	0.058 (4)	0.000 (3)	0.019 (3)	−0.001 (3)
O8	0.080 (5)	0.057 (4)	0.073 (4)	0.022 (3)	0.028 (3)	0.010 (3)
O9	0.041 (4)	0.081 (4)	0.069 (4)	0.004 (3)	0.012 (3)	−0.002 (3)
O10	0.110 (6)	0.039 (3)	0.066 (4)	−0.015 (4)	0.025 (4)	−0.003 (3)
O11	0.088 (5)	0.042 (3)	0.083 (4)	0.017 (3)	0.036 (4)	0.021 (3)

Ag1—N1	2.400 (6)	C16—C24	1.394 (7)
Ag1—N2	2.351 (6)	C16—C17	1.428 (7)
Ag1—N3	2.337 (6)	C17—O3	1.275 (7)
Ag1—N4	2.377 (6)	C17—C18	1.432 (8)
Ag1—O9	2.847 (6)	C18—O4	1.272 (9)
C1—N1	1.333 (9)	C18—C19	1.438 (8)
C1—C2	1.380 (11)	C19—C23	1.397 (7)
C1—H1	0.9300	C19—C20	1.419 (11)
C2—C3	1.383 (11)	C20—C21	1.361 (12)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.394 (10)	C21—C22	1.374 (12)
C3—H3	0.9300	C21—H21	0.9300
C4—C12	1.400 (7)	C22—N4	1.340 (10)
C4—C5	1.426 (8)	C22—H22	0.9300
C5—O1	1.304 (11)	C23—N4	1.373 (8)
C5—C6	1.385 (8)	C23—C24	1.433 (7)
C6—O2	1.293 (10)	C24—N3	1.362 (8)
C6—C7	1.417 (8)	C25—C30	1.390 (10)
C7—C11	1.390 (7)	C25—C26	1.426 (10)
C7—C8	1.438 (11)	C25—N5	1.454 (10)
C8—C9	1.358 (12)	C26—O7	1.292 (8)
C8—H8	0.9300	C26—C27	1.421 (10)
C9—C10	1.353 (12)	C27—C28	1.377 (10)
C9—H9	0.9300	C27—C31	1.498 (11)
C10—N2	1.347 (10)	C28—C29	1.416 (11)
C10—H10	0.9300	C28—H28	0.9300
C11—N2	1.353 (8)	C29—C30	1.374 (11)
C11—C12	1.432 (7)	C29—N6	1.448 (10)
C12—N1	1.365 (8)	C30—H30	0.9300
C13—N3	1.343 (10)	C31—O9	1.228 (10)
C13—C14	1.383 (12)	C31—O8	1.293 (10)
C13—H13	0.9300	N5—O6	1.218 (9)
C14—C15	1.376 (11)	N5—O5	1.230 (9)
C14—H14	0.9300	N6—O10	1.218 (9)
C15—C16	1.417 (10)	N6—O11	1.252 (9)
C15—H15	0.9300	O7—H7	0.8200
N3—Ag1—N2	115.0 (2)	O4—C18—C19	120.4 (7)
N3—Ag1—N4	70.7 (2)	C17—C18—C19	119.4 (7)
N2—Ag1—N4	174.1 (2)	C23—C19—C20	117.9 (7)
N3—Ag1—N1	130.3 (2)	C23—C19—C18	119.5 (7)
N2—Ag1—N1	71.5 (2)	C20—C19—C18	122.5 (7)
N4—Ag1—N1	106.3 (2)	C21—C20—C19	120.8 (7)
N3—Ag1—O9	147.53 (19)	C21—C20—H20	119.6
N2—Ag1—O9	76.74 (19)	C19—C20—H20	119.6
N4—Ag1—O9	97.64 (19)	C20—C21—C22	117.7 (8)
N1—Ag1—O9	81.75 (18)	C20—C21—H21	121.2
N1—C1—C2	124.2 (7)	C22—C21—H21	121.2
N1—C1—H1	117.9	N4—C22—C21	124.4 (8)
C2—C1—H1	117.9	N4—C22—H22	117.8
C1—C2—C3	117.6 (7)	C21—C22—H22	117.8
C1—C2—H2	121.2	N4—C23—C19	120.7 (6)
C3—C2—H2	121.2	N4—C23—C24	118.6 (6)
C2—C3—C4	119.9 (7)	C19—C23—C24	120.6 (6)
C2—C3—H3	120.0	N3—C24—C16	121.9 (6)
C4—C3—H3	120.0	N3—C24—C23	117.9 (6)
C3—C4—C12	119.1 (6)	C16—C24—C23	120.1 (6)
C3—C4—C5	121.0 (7)	C30—C25—C26	121.4 (7)
C12—C4—C5	119.9 (7)	C30—C25—N5	116.1 (7)
O1—C5—C6	118.0 (7)	C26—C25—N5	122.5 (7)
O1—C5—C4	120.7 (8)	O7—C26—C27	120.8 (7)
C6—C5—C4	121.3 (9)	O7—C26—C25	122.2 (7)
O2—C6—C5	120.3 (8)	C27—C26—C25	117.0 (6)
O2—C6—C7	122.0 (8)	C28—C27—C26	122.2 (7)
C5—C6—C7	117.8 (8)	C28—C27—C31	117.6 (7)
C11—C7—C6	122.8 (7)	C26—C27—C31	120.2 (7)
C11—C7—C8	117.1 (7)	C27—C28—C29	117.9 (7)
C6—C7—C8	120.1 (7)	C27—C28—H28	121.0
C9—C8—C7	119.4 (7)	C29—C28—H28	121.0
C9—C8—H8	120.3	C30—C29—C28	122.3 (7)
C7—C8—H8	120.3	C30—C29—N6	119.4 (8)
C10—C9—C8	119.5 (8)	C28—C29—N6	118.2 (8)
C10—C9—H9	120.3	C29—C30—C25	119.0 (7)
C8—C9—H9	120.3	C29—C30—H30	120.5
N2—C10—C9	123.6 (8)	C25—C30—H30	120.5
N2—C10—H10	118.2	O9—C31—O8	123.5 (8)
C9—C10—H10	118.2	O9—C31—C27	120.9 (8)
N2—C11—C7	122.1 (6)	O8—C31—C27	115.5 (8)
N2—C11—C12	119.3 (5)	C1—N1—C12	118.7 (6)
C7—C11—C12	118.6 (6)	C1—N1—Ag1	127.8 (5)
N1—C12—C4	120.6 (6)	C12—N1—Ag1	113.4 (4)
N1—C12—C11	119.9 (6)	C10—N2—C11	118.3 (6)
C4—C12—C11	119.5 (6)	C10—N2—Ag1	125.8 (5)
N3—C13—C14	123.8 (8)	C11—N2—Ag1	115.8 (4)
N3—C13—H13	118.1	C13—N3—C24	118.2 (6)
C14—C13—H13	118.1	C13—N3—Ag1	124.2 (5)
C15—C14—C13	118.2 (8)	C24—N3—Ag1	116.8 (4)
C15—C14—H14	120.9	C22—N4—C23	118.5 (6)
C13—C14—H14	120.9	C22—N4—Ag1	125.9 (5)
C14—C15—C16	119.8 (7)	C23—N4—Ag1	114.5 (4)
C14—C15—H15	120.1	O6—N5—O5	122.3 (8)
C16—C15—H15	120.1	O6—N5—C25	119.8 (8)
C24—C16—C15	118.0 (6)	O5—N5—C25	117.8 (8)
C24—C16—C17	120.3 (6)	O10—N6—O11	123.8 (7)
C15—C16—C17	121.7 (6)	O10—N6—C29	118.7 (8)
O3—C17—C18	120.3 (7)	O11—N6—C29	117.6 (8)
O3—C17—C16	120.4 (7)	C26—O7—H7	109.5
C18—C17—C16	119.3 (6)	C31—O9—Ag1	105.3 (5)
O4—C18—C17	120.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O8	0.82	1.71	2.457 (9)	151.

Table 1

Selected bond lengths (Å)

Ag1—N1	2.400 (6)
Ag1—N2	2.351 (6)
Ag1—N3	2.337 (6)
Ag1—N4	2.377 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O8	0.82	1.71	2.457 (9)	151