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The ortho­rhom­bic (space group Pna21) title compound, [Ag(C7H6NO2)]n, is a polymorph of the known monoclinic (P21/n) variant of this stoichiometry [Smith, Lynch & Kennard (1999). Aust. J. Chem. 52, 325–327]. In the title compound, the Ag atom shows linear coordination to one O and one N atom [Ag—O = 2.138 (5) Å, Ag—N = 2.153 (4) Å and O—Ag—N = 173.55 (18)°]. In the monoclinic form, the Ag coordination to two O atoms and one N atom can be described as Y-shaped or distorted trigonal planar. Weak Ag...Ag inter­actions, aromatic π–π stacking and N—H...O hydrogen-bond inter­actions help to establish the crystal packing in the title compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603409X/hb2130sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603409X/hb2130Isup2.hkl
Contains datablock I

CCDC reference: 621339

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.043
  • wR factor = 0.110
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.433 0.768 Tmin and Tmax expected: 0.378 0.757 RR = 1.130 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.12 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 O1 -AG1 -N1 -C1 -119.90 1.40 3.456 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 1621 Count of symmetry unique reflns 908 Completeness (_total/calc) 178.52% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 713 Fraction of Friedel pairs measured 0.785 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

poly[µ-2-aminobenzoato-silver(I)] top
Crystal data top
[Ag(C7H6NO2)]F(000) = 472
Mr = 244.00Dx = 2.293 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4705 reflections
a = 5.9486 (8) Åθ = 3.4–28.2°
b = 24.227 (3) ŵ = 2.79 mm1
c = 4.9042 (6) ÅT = 292 K
V = 706.77 (16) Å3Block, colorless
Z = 40.36 × 0.30 × 0.10 mm
Data collection top
Bruker APEX CCD
diffractometer
1621 independent reflections
Radiation source: fine-focus sealed tube1568 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.433, Tmax = 0.768k = 3131
7681 measured reflectionsl = 66
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0739P)2 + 0.1709P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
1621 reflectionsΔρmax = 1.69 e Å3
100 parametersΔρmin = 1.53 e Å3
1 restraintAbsolute structure: Flack (1983), 713 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (7)
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
Ag10.30013 (6)0.268478 (14)0.64846 (19)0.03900 (17)
O10.7161 (6)0.2898 (2)0.0406 (11)0.0436 (10)
O21.0353 (6)0.33698 (16)0.0752 (8)0.0421 (9)
N10.4014 (6)0.31953 (17)0.3109 (9)0.0325 (8)
H1A0.46640.29770.18510.039*
H1B0.27670.33380.23480.039*
C10.5527 (8)0.36411 (18)0.3688 (10)0.0283 (9)
C20.4904 (10)0.4029 (2)0.5644 (11)0.0408 (12)
H20.35350.39930.65430.049*
C30.6299 (11)0.4466 (2)0.6260 (18)0.0482 (13)
H30.58490.47260.75440.058*
C40.8373 (12)0.4522 (3)0.4980 (17)0.0498 (14)
H40.93230.48140.54130.060*
C50.8983 (9)0.41410 (19)0.3077 (13)0.0388 (11)
H51.03690.41780.22190.047*
C60.7593 (9)0.3691 (2)0.2355 (11)0.0293 (9)
C70.8446 (8)0.3294 (2)0.0234 (10)0.0291 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0337 (2)0.0491 (3)0.0342 (2)0.00793 (11)0.0032 (2)0.0076 (2)
O10.032 (2)0.046 (2)0.053 (3)0.0059 (16)0.0083 (18)0.014 (2)
O20.0224 (15)0.051 (2)0.053 (3)0.0018 (15)0.0090 (16)0.0057 (18)
N10.0228 (17)0.044 (2)0.030 (2)0.0030 (16)0.0008 (16)0.0045 (17)
C10.027 (2)0.033 (2)0.025 (2)0.0011 (17)0.0028 (17)0.0042 (17)
C20.042 (3)0.044 (3)0.037 (3)0.007 (2)0.007 (2)0.0025 (19)
C30.060 (3)0.041 (2)0.043 (3)0.005 (2)0.007 (4)0.006 (3)
C40.056 (3)0.039 (3)0.054 (4)0.007 (3)0.003 (3)0.008 (3)
C50.034 (2)0.033 (2)0.050 (3)0.005 (2)0.004 (2)0.003 (2)
C60.0269 (18)0.030 (2)0.031 (2)0.0025 (18)0.0009 (17)0.0025 (17)
C70.0225 (19)0.036 (2)0.029 (3)0.0037 (19)0.0011 (19)0.0043 (19)
Geometric parameters (Å, º) top
Ag1—O1i2.138 (5)C1—C61.397 (7)
Ag1—N12.153 (4)C2—C31.379 (8)
Ag1—Ag1ii3.1061 (4)C2—H20.9300
Ag1—Ag1iii3.1061 (4)C3—C41.391 (10)
C7—O11.264 (7)C3—H30.9300
C7—O21.247 (6)C4—C51.363 (9)
O1—Ag1iv2.138 (5)C4—H40.9300
N1—C11.434 (6)C5—C61.413 (7)
N1—H1A0.9000C5—H50.9300
N1—H1B0.9000C6—C71.506 (8)
C1—C21.393 (7)
O1i—Ag1—N1173.55 (18)C3—C2—H2119.7
O1i—Ag1—Ag1ii65.53 (11)C1—C2—H2119.7
N1—Ag1—Ag1ii115.70 (11)C2—C3—C4120.6 (6)
O1i—Ag1—Ag1iii91.91 (10)C2—C3—H3119.7
N1—Ag1—Ag1iii84.12 (11)C4—C3—H3119.7
Ag1ii—Ag1—Ag1iii146.49 (3)C5—C4—C3118.6 (6)
C7—O1—Ag1iv122.4 (3)C5—C4—H4120.7
C1—N1—Ag1117.1 (3)C3—C4—H4120.7
C1—N1—H1A108.0C4—C5—C6122.6 (5)
Ag1—N1—H1A108.0C4—C5—H5118.7
C1—N1—H1B108.0C6—C5—H5118.7
Ag1—N1—H1B108.0C1—C6—C5117.7 (5)
H1A—N1—H1B107.3C1—C6—C7124.3 (5)
C2—C1—C6119.8 (5)C5—C6—C7118.0 (5)
C2—C1—N1118.5 (4)O2—C7—O1124.4 (5)
C6—C1—N1121.6 (4)O2—C7—C6118.7 (5)
C3—C2—C1120.6 (5)O1—C7—C6116.9 (4)
O1i—Ag1—N1—C1119.9 (14)N1—C1—C6—C5179.4 (5)
Ag1ii—Ag1—N1—C1140.6 (3)C2—C1—C6—C7179.3 (5)
Ag1iii—Ag1—N1—C167.6 (3)N1—C1—C6—C70.3 (7)
Ag1—N1—C1—C256.3 (5)C4—C5—C6—C10.6 (8)
Ag1—N1—C1—C6123.4 (4)C4—C5—C6—C7179.7 (6)
C6—C1—C2—C30.7 (8)Ag1iv—O1—C7—O23.8 (8)
N1—C1—C2—C3179.7 (5)Ag1iv—O1—C7—C6176.8 (4)
C1—C2—C3—C41.3 (10)C1—C6—C7—O2177.6 (5)
C2—C3—C4—C50.9 (11)C5—C6—C7—O21.5 (7)
C3—C4—C5—C60.0 (10)C1—C6—C7—O11.8 (8)
C2—C1—C6—C50.2 (7)C5—C6—C7—O1179.1 (5)
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x1/2, y+1/2, z; (iii) x+1/2, y+1/2, z; (iv) x+1/2, y+1/2, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.901.862.644 (6)144
N1—H1B···O2v0.902.092.917 (6)152
Symmetry code: (v) x1, y, z.
 

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