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ISSN: 2056-9890

Bis{1-[(benzo­yl­oxy)meth­yl]-1H-1,2,3-benzotriazole-κN3}(nitrato-κ2O,O′)­silver(I)

aDepartment of Applied Chemistry, School of Materials Science and Engineering, Nanjing University of Aeronautics and Astronautics, Nanjing, Jiangsu Province 210016, People's Republic of China
*Correspondence e-mail: xusennuaa@163.com

(Received 2 December 2011; accepted 13 February 2012; online 3 March 2012)

In the crystal structure of the title coordination compound, [Ag(NO3)(C14H11N3O2)2], the AgI atom is four-coordinated in a distorted tetra­hedral geometry by two O atoms from one nitrate group and two N atoms from two different 1-[(benzo­yloxy)meth­yl]-1H-1,2,3-triazole ligands. In the complex, the two coordinated benzotriazole rings rings are nearly perpendicular, the dihedral angle between their planes being 87.08 (6)°.

Related literature

For related structures, see: Han et al. (2008[Han, X. L., An, C. X. & Zhang, Z. H. (2008). Appl. Organomet. Chem. 22, 565-572.]); Zhou et al. (2011[Zhou, X. L., Li, W. Q., Jin, G. H., Zhao, D., Zhu, X. Q., Meng, X. R. & Hou, H. W. (2011). J. Mol. Struct. 995, 148-156.]).

[Scheme 1]

Experimental

Crystal data
  • [Ag(NO3)(C14H11N3O2)2]

  • Mr = 676.40

  • Triclinic, [P \overline 1]

  • a = 9.8815 (5) Å

  • b = 10.6695 (5) Å

  • c = 15.0158 (7) Å

  • α = 70.405 (2)°

  • β = 73.323 (2)°

  • γ = 74.974 (2)°

  • V = 1405.21 (12) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.78 mm−1

  • T = 296 K

  • 0.20 × 0.18 × 0.17 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SABADS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.860, Tmax = 0.879

  • 19832 measured reflections

  • 4947 independent reflections

  • 4563 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.067

  • S = 1.13

  • 4947 reflections

  • 404 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.46 e Å−3

Table 1
Selected bond lengths (Å)

Ag1—N3 2.238 (2)
Ag1—N4 2.219 (2)
Ag1—O1 2.690 (2)
Ag1—O2 2.513 (2)

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Benzotriazol derivatives have been widely used for constructing complexes with transition metals (see e.g.: Han et al., 2008; Zhou et al., 2011). In this contribution, a new coordination compound was synthesized using (1H-benzo[d][1,2,3]triazol-1-yl)methyl benzoate and silver nitrate and characterized by single-crystal X-ray diffraction. The crystal structure of the title compound is shown in Fig.1. The AgI atom is four-coordinated in a slightly distorted tetradral geometry by two O atoms from one nitrate and two N atoms from two (1H-benzo[d][1,2,3]triazol-1-yl)methyl benzoate ligands. The bond distances Ag—N (Ag1—N3=2.238 (2) Å, Ag1—N4=2.219 (2) Å), and Ag—O (Ag1—O1=2.690 (2) Å, Ag1—O2=2.513 (2) Å) are within normal ranges.

Related literature top

For related structures, see: Han et al. (2008); Zhou et al. (2011).

Experimental top

(1H-benzo[d][1,2,3]triazol-1-yl)methyl benzoate (0.25 mmol) and silver nitrate (0.25 mmol) were mixed in a round bottom flask with 10 ml absolute ethyl alcohol, and stirred for 10 hours. After the completion of the reaction a white solid was obtained from which a small amount was dissolved in absolute ethyl alcohol, and single crystals were obtained by slow evaporation.

Refinement top

All H atoms were situated at idealized positions with carrier atom—H distances at 0.93Å for aryl groups, and they were treated using a riding model approximation with Uiso(H) = 1.2Ueq(C). H atoms bonded to methylene were refined independently with isotropic displacement parameters. The Ag1 and O2 sites were treated with a SHELXL DELU instruction.

Structure description top

Benzotriazol derivatives have been widely used for constructing complexes with transition metals (see e.g.: Han et al., 2008; Zhou et al., 2011). In this contribution, a new coordination compound was synthesized using (1H-benzo[d][1,2,3]triazol-1-yl)methyl benzoate and silver nitrate and characterized by single-crystal X-ray diffraction. The crystal structure of the title compound is shown in Fig.1. The AgI atom is four-coordinated in a slightly distorted tetradral geometry by two O atoms from one nitrate and two N atoms from two (1H-benzo[d][1,2,3]triazol-1-yl)methyl benzoate ligands. The bond distances Ag—N (Ag1—N3=2.238 (2) Å, Ag1—N4=2.219 (2) Å), and Ag—O (Ag1—O1=2.690 (2) Å, Ag1—O2=2.513 (2) Å) are within normal ranges.

For related structures, see: Han et al. (2008); Zhou et al. (2011).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Bis{1-[(benzoyloxy)methyl]-1H-1,2,3-triazole- κN3}(nitrato-κ2O,O')silver(I) top
Crystal data top
[Ag(NO3)(C14H11N3O2)2]Z = 2
Mr = 676.40F(000) = 684
Triclinic, P1Dx = 1.599 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8815 (5) ÅCell parameters from 9998 reflections
b = 10.6695 (5) Åθ = 2.7–27.7°
c = 15.0158 (7) ŵ = 0.78 mm1
α = 70.405 (2)°T = 296 K
β = 73.323 (2)°Block, colourless
γ = 74.974 (2)°0.20 × 0.18 × 0.17 mm
V = 1405.21 (12) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4947 independent reflections
Radiation source: fine-focus sealed tube4563 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SABADS; Sheldrick, 1996)
h = 1111
Tmin = 0.860, Tmax = 0.879k = 1212
19832 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0116P)2 + 0.9774P]
where P = (Fo2 + 2Fc2)/3
4947 reflections(Δ/σ)max = 0.001
404 parametersΔρmax = 0.31 e Å3
1 restraintΔρmin = 0.46 e Å3
Crystal data top
[Ag(NO3)(C14H11N3O2)2]γ = 74.974 (2)°
Mr = 676.40V = 1405.21 (12) Å3
Triclinic, P1Z = 2
a = 9.8815 (5) ÅMo Kα radiation
b = 10.6695 (5) ŵ = 0.78 mm1
c = 15.0158 (7) ÅT = 296 K
α = 70.405 (2)°0.20 × 0.18 × 0.17 mm
β = 73.323 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4947 independent reflections
Absorption correction: multi-scan
(SABADS; Sheldrick, 1996)
4563 reflections with I > 2σ(I)
Tmin = 0.860, Tmax = 0.879Rint = 0.031
19832 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0321 restraint
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.31 e Å3
4947 reflectionsΔρmin = 0.46 e Å3
404 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
Ag10.03724 (2)0.57849 (2)0.088297 (16)0.05262 (8)
C10.0863 (3)0.3081 (2)0.23322 (18)0.0368 (5)
C20.1554 (3)0.3546 (3)0.3143 (2)0.0483 (7)
H20.16420.44420.31280.058*
C30.2095 (3)0.2608 (3)0.3964 (2)0.0568 (8)
H30.25600.28770.45220.068*
C40.1969 (3)0.1258 (3)0.3991 (2)0.0580 (8)
H40.23440.06580.45680.070*
C50.1318 (3)0.0794 (3)0.32016 (19)0.0498 (7)
H50.12490.01000.32200.060*
C60.0759 (3)0.1743 (2)0.23637 (18)0.0366 (5)
C70.0367 (3)0.0503 (3)0.1079 (2)0.0426 (6)
C80.2437 (3)0.0951 (2)0.16086 (19)0.0395 (6)
C90.2897 (3)0.2079 (3)0.24241 (19)0.0421 (6)
C100.4303 (3)0.2301 (3)0.2521 (2)0.0560 (8)
H100.49280.17400.20850.067*
C110.4774 (4)0.3351 (3)0.3264 (3)0.0682 (9)
H110.57090.34850.33360.082*
C120.3867 (4)0.4196 (3)0.3893 (2)0.0690 (10)
H120.41910.49110.43870.083*
C130.2474 (4)0.3988 (3)0.3796 (2)0.0666 (9)
H130.18650.45700.42240.080*
C140.1973 (3)0.2923 (3)0.3070 (2)0.0544 (7)
H140.10270.27760.30150.065*
C150.3679 (3)0.6112 (2)0.06858 (18)0.0373 (6)
C160.4652 (3)0.6949 (2)0.01166 (17)0.0351 (5)
C170.6031 (3)0.6754 (3)0.0275 (2)0.0469 (7)
H170.66780.73260.01040.056*
C180.6355 (3)0.5662 (3)0.1026 (2)0.0567 (8)
H180.72590.54820.11610.068*
C190.5382 (4)0.4799 (3)0.1604 (2)0.0557 (8)
H190.56660.40660.21030.067*
C200.4033 (3)0.5004 (3)0.1457 (2)0.0483 (7)
H200.33840.44400.18480.058*
C210.4355 (3)0.9080 (3)0.1274 (2)0.0441 (6)
C220.6299 (3)0.8467 (3)0.2501 (2)0.0446 (6)
C230.6691 (3)0.8206 (3)0.34636 (19)0.0462 (7)
C240.5683 (4)0.8326 (3)0.3974 (2)0.0638 (9)
H240.47120.85940.37250.077*
C250.6129 (5)0.8043 (4)0.4860 (3)0.0789 (11)
H250.54560.81250.52100.095*
C260.7561 (5)0.7642 (4)0.5223 (2)0.0769 (11)
H260.78540.74440.58150.092*
C270.8553 (5)0.7534 (4)0.4723 (3)0.0802 (11)
H270.95230.72670.49740.096*
C280.8126 (4)0.7820 (4)0.3842 (2)0.0660 (9)
H280.88080.77520.35040.079*
H1A0.356 (3)0.977 (3)0.1326 (17)0.037 (7)*
H2A0.510 (3)0.935 (3)0.1106 (19)0.047 (8)*
H3A0.054 (3)0.029 (3)0.1051 (18)0.041 (7)*
H4A0.102 (3)0.072 (3)0.048 (2)0.045 (8)*
N10.3925 (2)0.7905 (2)0.05326 (14)0.0363 (5)
N20.2574 (2)0.7682 (2)0.03701 (16)0.0408 (5)
N30.2419 (2)0.6601 (2)0.03592 (15)0.0413 (5)
N40.0186 (2)0.3735 (2)0.14134 (15)0.0385 (5)
N50.0324 (2)0.2868 (2)0.09009 (14)0.0374 (5)
N60.0017 (2)0.1661 (2)0.14623 (14)0.0357 (5)
N70.1525 (3)0.7667 (2)0.20292 (16)0.0459 (5)
O10.0939 (3)0.6566 (2)0.24968 (17)0.0739 (7)
O20.1332 (3)0.7897 (2)0.11432 (15)0.0781 (7)
O30.2257 (3)0.8530 (2)0.24265 (16)0.0714 (7)
O40.3217 (2)0.0385 (2)0.08958 (14)0.0524 (5)
O50.7136 (2)0.8368 (3)0.20369 (16)0.0681 (6)
O60.09795 (19)0.06300 (17)0.17626 (13)0.0451 (4)
O70.48595 (19)0.8807 (2)0.21973 (13)0.0483 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.05344 (14)0.04608 (14)0.05684 (15)0.02381 (11)0.00015 (10)0.01177 (10)
C10.0334 (13)0.0346 (13)0.0404 (13)0.0081 (11)0.0092 (11)0.0056 (11)
C20.0501 (16)0.0422 (15)0.0543 (17)0.0074 (13)0.0074 (13)0.0199 (13)
C30.0606 (19)0.062 (2)0.0452 (16)0.0159 (16)0.0030 (14)0.0198 (15)
C40.068 (2)0.0533 (18)0.0432 (16)0.0226 (16)0.0033 (14)0.0060 (14)
C50.0619 (18)0.0394 (15)0.0448 (15)0.0181 (14)0.0049 (14)0.0067 (12)
C60.0354 (13)0.0365 (14)0.0379 (13)0.0088 (11)0.0095 (11)0.0075 (11)
C70.0488 (17)0.0329 (14)0.0429 (15)0.0027 (12)0.0124 (13)0.0083 (12)
C80.0449 (15)0.0325 (13)0.0442 (15)0.0059 (12)0.0091 (12)0.0161 (11)
C90.0491 (16)0.0340 (14)0.0447 (15)0.0022 (12)0.0129 (12)0.0147 (11)
C100.0554 (18)0.0443 (17)0.070 (2)0.0069 (14)0.0224 (16)0.0125 (15)
C110.068 (2)0.057 (2)0.084 (2)0.0001 (17)0.0385 (19)0.0165 (18)
C120.090 (3)0.053 (2)0.059 (2)0.0075 (19)0.0331 (19)0.0116 (16)
C130.079 (2)0.0532 (19)0.0505 (18)0.0085 (17)0.0120 (17)0.0020 (15)
C140.0580 (18)0.0485 (17)0.0489 (16)0.0069 (14)0.0115 (14)0.0061 (14)
C150.0380 (14)0.0325 (13)0.0404 (14)0.0050 (11)0.0066 (11)0.0117 (11)
C160.0364 (13)0.0337 (13)0.0341 (13)0.0031 (11)0.0072 (10)0.0111 (10)
C170.0364 (14)0.0519 (17)0.0514 (16)0.0054 (12)0.0105 (12)0.0146 (13)
C180.0496 (17)0.0618 (19)0.0608 (19)0.0003 (15)0.0267 (15)0.0150 (16)
C190.070 (2)0.0445 (17)0.0494 (17)0.0031 (15)0.0252 (15)0.0085 (14)
C200.0600 (18)0.0347 (14)0.0448 (15)0.0086 (13)0.0081 (13)0.0069 (12)
C210.0386 (15)0.0361 (15)0.0483 (16)0.0064 (13)0.0051 (13)0.0043 (12)
C220.0413 (15)0.0431 (15)0.0450 (15)0.0094 (12)0.0100 (13)0.0051 (12)
C230.0511 (17)0.0435 (15)0.0378 (14)0.0125 (13)0.0101 (12)0.0003 (12)
C240.065 (2)0.076 (2)0.0505 (18)0.0199 (18)0.0161 (16)0.0107 (16)
C250.104 (3)0.089 (3)0.054 (2)0.032 (2)0.029 (2)0.0114 (19)
C260.122 (4)0.064 (2)0.0398 (17)0.028 (2)0.006 (2)0.0104 (16)
C270.087 (3)0.087 (3)0.053 (2)0.010 (2)0.003 (2)0.0227 (19)
C280.058 (2)0.081 (2)0.0524 (18)0.0049 (18)0.0115 (16)0.0174 (17)
N10.0310 (11)0.0339 (11)0.0402 (11)0.0085 (9)0.0055 (9)0.0058 (9)
N20.0325 (11)0.0382 (12)0.0486 (13)0.0078 (9)0.0095 (10)0.0070 (10)
N30.0381 (12)0.0376 (12)0.0467 (12)0.0120 (10)0.0071 (10)0.0079 (10)
N40.0384 (12)0.0321 (11)0.0425 (12)0.0091 (9)0.0098 (9)0.0046 (9)
N50.0387 (12)0.0328 (11)0.0380 (11)0.0083 (9)0.0102 (9)0.0038 (9)
N60.0391 (11)0.0308 (11)0.0355 (11)0.0080 (9)0.0105 (9)0.0040 (9)
N70.0522 (14)0.0410 (13)0.0445 (13)0.0126 (11)0.0101 (11)0.0095 (11)
O10.0951 (18)0.0394 (12)0.0766 (15)0.0012 (12)0.0284 (14)0.0034 (11)
O20.107 (2)0.0733 (14)0.0446 (12)0.0052 (11)0.0174 (13)0.0211 (11)
O30.0898 (17)0.0583 (14)0.0629 (14)0.0131 (12)0.0205 (12)0.0298 (12)
O40.0490 (11)0.0503 (12)0.0503 (11)0.0117 (9)0.0046 (9)0.0078 (9)
O50.0436 (12)0.1073 (19)0.0633 (13)0.0018 (12)0.0169 (11)0.0413 (13)
O60.0439 (11)0.0348 (10)0.0467 (10)0.0026 (8)0.0100 (8)0.0023 (8)
O70.0395 (10)0.0584 (12)0.0406 (10)0.0123 (9)0.0082 (8)0.0037 (9)
Geometric parameters (Å, º) top
Ag1—N32.238 (2)C15—C201.400 (4)
Ag1—N42.219 (2)C16—N11.364 (3)
Ag1—O12.690 (2)C16—C171.401 (4)
Ag1—O22.513 (2)C17—C181.366 (4)
C1—N41.380 (3)C17—H170.9300
C1—C61.391 (3)C18—C191.403 (4)
C1—C21.395 (4)C18—H180.9300
C2—C31.371 (4)C19—C201.364 (4)
C2—H20.9300C19—H190.9300
C3—C41.402 (4)C20—H200.9300
C3—H30.9300C21—O71.433 (3)
C4—C51.362 (4)C21—N11.435 (3)
C4—H40.9300C21—H1A0.93 (3)
C5—C61.396 (3)C21—H2A0.98 (3)
C5—H50.9300C22—O51.191 (3)
C6—N61.361 (3)C22—O71.354 (3)
C7—O61.423 (3)C22—C231.486 (4)
C7—N61.452 (3)C23—C281.377 (4)
C7—H3A1.00 (3)C23—C241.379 (4)
C7—H4A0.94 (3)C24—C251.386 (5)
C8—O41.200 (3)C24—H240.9300
C8—O61.361 (3)C25—C261.372 (5)
C8—C91.484 (4)C25—H250.9300
C9—C141.385 (4)C26—C271.359 (5)
C9—C101.388 (4)C26—H260.9300
C10—C111.381 (4)C27—C281.379 (5)
C10—H100.9300C27—H270.9300
C11—C121.367 (5)C28—H280.9300
C11—H110.9300N1—N21.355 (3)
C12—C131.379 (5)N2—N31.304 (3)
C12—H120.9300N4—N51.310 (3)
C13—C141.383 (4)N5—N61.348 (3)
C13—H130.9300N7—O31.226 (3)
C14—H140.9300N7—O21.235 (3)
C15—N31.381 (3)N7—O11.239 (3)
C15—C161.384 (3)
N4—Ag1—N3135.16 (8)C18—C17—H17122.5
N4—Ag1—O2124.85 (8)C16—C17—H17122.5
N3—Ag1—O298.41 (8)C17—C18—C19122.9 (3)
N3—Ag1—O1104.13 (8)C17—C18—H18118.6
N4—Ag1—O197.67 (7)C19—C18—H18118.6
O1—Ag1—O248.14 (7)C20—C19—C18122.0 (3)
N4—C1—C6107.6 (2)C20—C19—H19119.0
N4—C1—C2131.2 (2)C18—C19—H19119.0
C6—C1—C2121.1 (2)C19—C20—C15116.3 (3)
C3—C2—C1116.3 (3)C19—C20—H20121.9
C3—C2—H2121.9C15—C20—H20121.9
C1—C2—H2121.9O7—C21—N1110.4 (2)
C2—C3—C4122.1 (3)O7—C21—H1A106.5 (15)
C2—C3—H3119.0N1—C21—H1A109.1 (15)
C4—C3—H3119.0O7—C21—H2A110.9 (16)
C5—C4—C3122.3 (3)N1—C21—H2A109.2 (16)
C5—C4—H4118.8H1A—C21—H2A111 (2)
C3—C4—H4118.8O5—C22—O7123.4 (3)
C4—C5—C6115.9 (3)O5—C22—C23124.7 (3)
C4—C5—H5122.0O7—C22—C23111.9 (2)
C6—C5—H5122.0C28—C23—C24119.8 (3)
N6—C6—C1104.6 (2)C28—C23—C22117.5 (3)
N6—C6—C5133.1 (2)C24—C23—C22122.7 (3)
C1—C6—C5122.3 (2)C23—C24—C25119.4 (3)
O6—C7—N6108.1 (2)C23—C24—H24120.3
O6—C7—H3A106.2 (15)C25—C24—H24120.3
N6—C7—H3A107.7 (15)C26—C25—C24120.1 (4)
O6—C7—H4A111.9 (16)C26—C25—H25119.9
N6—C7—H4A108.1 (17)C24—C25—H25119.9
H3A—C7—H4A115 (2)C27—C26—C25120.3 (3)
O4—C8—O6123.1 (2)C27—C26—H26119.8
O4—C8—C9126.0 (2)C25—C26—H26119.8
O6—C8—C9111.0 (2)C26—C27—C28120.1 (4)
C14—C9—C10119.8 (3)C26—C27—H27119.9
C14—C9—C8121.7 (3)C28—C27—H27119.9
C10—C9—C8118.5 (3)C23—C28—C27120.2 (3)
C11—C10—C9120.2 (3)C23—C28—H28119.9
C11—C10—H10119.9C27—C28—H28119.9
C9—C10—H10119.9N2—N1—C16110.71 (19)
C12—C11—C10120.1 (3)N2—N1—C21119.2 (2)
C12—C11—H11120.0C16—N1—C21129.9 (2)
C10—C11—H11120.0N3—N2—N1107.9 (2)
C11—C12—C13120.1 (3)N2—N3—C15109.0 (2)
C11—C12—H12120.0N2—N3—Ag1121.42 (16)
C13—C12—H12120.0C15—N3—Ag1129.61 (16)
C12—C13—C14120.7 (3)N5—N4—C1108.88 (19)
C12—C13—H13119.7N5—N4—Ag1121.83 (15)
C14—C13—H13119.7C1—N4—Ag1128.42 (17)
C13—C14—C9119.2 (3)N4—N5—N6108.24 (19)
C13—C14—H14120.4N5—N6—C6110.6 (2)
C9—C14—H14120.4N5—N6—C7120.9 (2)
N3—C15—C16108.2 (2)C6—N6—C7128.4 (2)
N3—C15—C20130.6 (2)O3—N7—O2120.0 (2)
C16—C15—C20121.2 (2)O3—N7—O1121.2 (2)
N1—C16—C15104.3 (2)O2—N7—O1118.7 (3)
N1—C16—C17133.0 (2)N7—O2—Ag1100.98 (17)
C15—C16—C17122.7 (2)C8—O6—C7117.8 (2)
C18—C17—C16115.0 (3)C22—O7—C21116.8 (2)
N4—C1—C2—C3178.6 (3)O7—C21—N1—C1698.7 (3)
C6—C1—C2—C31.0 (4)C16—N1—N2—N30.6 (3)
C1—C2—C3—C40.2 (5)C21—N1—N2—N3177.1 (2)
C2—C3—C4—C50.8 (5)N1—N2—N3—C150.4 (3)
C3—C4—C5—C61.0 (5)N1—N2—N3—Ag1178.42 (15)
N4—C1—C6—N60.3 (3)C16—C15—N3—N20.1 (3)
C2—C1—C6—N6179.3 (2)C20—C15—N3—N2178.3 (3)
N4—C1—C6—C5178.9 (2)C16—C15—N3—Ag1178.64 (16)
C2—C1—C6—C50.8 (4)C20—C15—N3—Ag12.9 (4)
C4—C5—C6—N6177.9 (3)N4—Ag1—N3—N2140.36 (18)
C4—C5—C6—C10.2 (4)O2—Ag1—N3—N254.18 (19)
O4—C8—C9—C14161.0 (3)O1—Ag1—N3—N2103.01 (19)
O6—C8—C9—C1418.4 (3)N4—Ag1—N3—C1538.2 (3)
O4—C8—C9—C1017.5 (4)O2—Ag1—N3—C15127.2 (2)
O6—C8—C9—C10163.0 (2)O1—Ag1—N3—C1578.4 (2)
C14—C9—C10—C110.6 (4)C6—C1—N4—N50.6 (3)
C8—C9—C10—C11179.2 (3)C2—C1—N4—N5179.0 (3)
C9—C10—C11—C121.5 (5)C6—C1—N4—Ag1169.87 (16)
C10—C11—C12—C131.0 (5)C2—C1—N4—Ag19.7 (4)
C11—C12—C13—C140.4 (5)N3—Ag1—N4—N555.2 (2)
C12—C13—C14—C91.3 (5)O2—Ag1—N4—N5142.44 (17)
C10—C9—C14—C130.8 (4)O1—Ag1—N4—N5174.17 (18)
C8—C9—C14—C13177.7 (3)N3—Ag1—N4—C1112.9 (2)
N3—C15—C16—N10.3 (3)O2—Ag1—N4—C149.5 (2)
C20—C15—C16—N1178.9 (2)O1—Ag1—N4—C16.1 (2)
N3—C15—C16—C17178.2 (2)C1—N4—N5—N60.6 (3)
C20—C15—C16—C170.4 (4)Ag1—N4—N5—N6170.76 (14)
N1—C16—C17—C18178.9 (3)N4—N5—N6—C60.4 (3)
C15—C16—C17—C180.9 (4)N4—N5—N6—C7177.9 (2)
C16—C17—C18—C190.4 (4)C1—C6—N6—N50.1 (3)
C17—C18—C19—C200.6 (5)C5—C6—N6—N5178.3 (3)
C18—C19—C20—C151.1 (4)C1—C6—N6—C7178.2 (2)
N3—C15—C20—C19178.8 (3)C5—C6—N6—C73.5 (5)
C16—C15—C20—C190.6 (4)O6—C7—N6—N5133.5 (2)
O5—C22—C23—C280.2 (5)O6—C7—N6—C648.4 (3)
O7—C22—C23—C28178.6 (3)O3—N7—O1—Ag1176.1 (2)
O5—C22—C23—C24179.6 (3)O2—N7—O1—Ag12.3 (3)
O7—C22—C23—C240.9 (4)N4—Ag1—O1—N7132.13 (17)
C28—C23—C24—C250.6 (5)N3—Ag1—O1—N787.37 (17)
C22—C23—C24—C25178.9 (3)O2—Ag1—O1—N71.32 (16)
C23—C24—C25—C260.3 (5)O3—N7—O2—Ag1175.9 (2)
C24—C25—C26—C270.7 (6)O1—N7—O2—Ag12.5 (3)
C25—C26—C27—C280.4 (6)N4—Ag1—O2—N767.4 (2)
C24—C23—C28—C271.0 (5)N3—Ag1—O2—N7100.12 (19)
C22—C23—C28—C27178.5 (3)O1—Ag1—O2—N71.35 (16)
C26—C27—C28—C230.5 (6)O4—C8—O6—C75.3 (4)
C15—C16—N1—N20.6 (3)C9—C8—O6—C7175.3 (2)
C17—C16—N1—N2177.7 (3)N6—C7—O6—C897.7 (3)
C15—C16—N1—C21176.5 (2)O5—C22—O7—C211.2 (4)
C17—C16—N1—C211.8 (5)C23—C22—O7—C21179.9 (2)
O7—C21—N1—N285.7 (3)N1—C21—O7—C2297.4 (3)

Experimental details

Crystal data
Chemical formula[Ag(NO3)(C14H11N3O2)2]
Mr676.40
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.8815 (5), 10.6695 (5), 15.0158 (7)
α, β, γ (°)70.405 (2), 73.323 (2), 74.974 (2)
V3)1405.21 (12)
Z2
Radiation typeMo Kα
µ (mm1)0.78
Crystal size (mm)0.20 × 0.18 × 0.17
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SABADS; Sheldrick, 1996)
Tmin, Tmax0.860, 0.879
No. of measured, independent and
observed [I > 2σ(I)] reflections
19832, 4947, 4563
Rint0.031
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.067, 1.13
No. of reflections4947
No. of parameters404
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.46

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Ag1—N32.238 (2)Ag1—O12.690 (2)
Ag1—N42.219 (2)Ag1—O22.513 (2)
 

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHan, X. L., An, C. X. & Zhang, Z. H. (2008). Appl. Organomet. Chem. 22, 565–572.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhou, X. L., Li, W. Q., Jin, G. H., Zhao, D., Zhu, X. Q., Meng, X. R. & Hou, H. W. (2011). J. Mol. Struct. 995, 148–156.  Web of Science CSD CrossRef CAS Google Scholar

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