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In the crystal structure of the title complex, [Ag(C12H12N2O)2]NO3·H2O, the AgI atom is coordinated by two imidazole N atoms from two 3-(1H-imidazol-1-yl)-1-phenyl­propan-1-one ligands that are trans to each other. Inter­molecular O—H...O and C—H...O hydrogen bonds exist between adjacent mol­ecules, resulting in a three-dimensional supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010008/hy2042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010008/hy2042Isup2.hkl
Contains datablock I

CCDC reference: 643653

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.042
  • wR factor = 0.117
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O6 - H6B ... ?
Alert level C PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.40 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.40
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 25.03 From the CIF: _reflns_number_total 3706 Count of symmetry unique reflns 2207 Completeness (_total/calc) 167.92% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1499 Fraction of Friedel pairs measured 0.679 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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
checkCIF publication errors
Alert level A PUBL023_ALERT_1_A There is a mismatched ^ on line 80 Bis[3-(1H-imidazol-1-yl-\kN^3)-1-phenylpropan-1-one]silver(I) nitrate If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C PUBL023_ALERT_1_A There is a mismatched ^ on line 236 Bis[3-(1H-imidazol-1-yl-\kN^3)-1-phenylpropan-1-one]silver(I) nitrate If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C
2 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXTL.

Bis[3-(1H-imidazol-1-yl-κN3)-1-phenylpropan-1-one]silver(I) nitrate monohydrate top
Crystal data top
[Ag(C12H12N2O)2]NO3·H2OF(000) = 1200
Mr = 588.37Dx = 1.599 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2119 reflections
a = 10.361 (3) Åθ = 2.6–18.4°
b = 8.321 (3) ŵ = 0.88 mm1
c = 28.349 (9) ÅT = 293 K
V = 2443.9 (13) Å3Block, colorless
Z = 40.24 × 0.20 × 0.18 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
3706 independent reflections
Radiation source: fine-focus sealed tube2553 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1112
Tmin = 0.818, Tmax = 0.858k = 99
12458 measured reflectionsl = 2733
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)] = 0.042H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0647P)2 + 0.015P]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
3706 reflectionsΔρmax = 0.67 e Å3
326 parametersΔρmin = 0.51 e Å3
1 restraintAbsolute structure: Flack (1983), 1101 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.0 (4)
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
Ag10.47250 (5)0.29969 (6)0.76519 (2)0.0645 (2)
O11.0687 (5)0.3110 (7)0.9519 (2)0.0782 (17)
O20.0826 (6)0.2064 (8)0.5660 (2)0.0851 (18)
O30.3406 (7)0.1119 (8)0.2366 (2)0.092 (2)
O40.4177 (8)0.0442 (9)0.3030 (3)0.129 (3)
O50.2152 (7)0.0465 (7)0.2925 (3)0.097 (2)
N10.3447 (6)0.1871 (6)0.71905 (19)0.0541 (14)
N20.1880 (5)0.1286 (7)0.67019 (18)0.0472 (13)
N30.6156 (5)0.3944 (7)0.80879 (19)0.0558 (14)
N40.7893 (6)0.4161 (6)0.85149 (19)0.0492 (13)
N50.3233 (8)0.0678 (7)0.2783 (3)0.0660 (19)
C10.2474 (8)0.0118 (9)0.6814 (3)0.065 (2)
H10.22630.11320.67000.078*
C20.3416 (7)0.0229 (9)0.7119 (3)0.064 (2)
H20.39630.05150.72610.077*
C30.2504 (8)0.2440 (9)0.6937 (3)0.053 (2)
H30.22900.35240.69210.064*
C40.0821 (7)0.1504 (8)0.6372 (2)0.0545 (17)
H4A0.05070.26000.63940.065*
H4B0.01190.07900.64580.065*
C50.1220 (6)0.1169 (8)0.5877 (2)0.0495 (15)
H5A0.14460.00420.58490.059*
H5B0.19860.17940.58050.059*
C60.0203 (7)0.1552 (9)0.5521 (3)0.0546 (18)
C70.0444 (6)0.1333 (8)0.5015 (2)0.0504 (16)
C80.1536 (6)0.0577 (8)0.4836 (3)0.0578 (18)
H80.21520.01730.50430.069*
C90.1721 (8)0.0415 (9)0.4359 (3)0.065 (2)
H90.24610.00880.42460.078*
C100.0821 (9)0.0991 (9)0.4048 (3)0.072 (2)
H100.09340.08640.37250.086*
C110.0266 (9)0.1772 (11)0.4224 (3)0.078 (2)
H110.08720.21950.40170.094*
C120.0446 (8)0.1921 (9)0.4691 (3)0.070 (2)
H120.11860.24300.48000.084*
C130.6982 (8)0.3189 (9)0.8356 (3)0.0520 (19)
H130.69360.20990.84270.062*
C140.6559 (8)0.5533 (9)0.8081 (3)0.069 (2)
H140.61610.63700.79190.082*
C150.7614 (9)0.5651 (10)0.8347 (3)0.069 (2)
H150.80780.65860.84060.082*
C160.8955 (7)0.3761 (8)0.8833 (2)0.0532 (16)
H16A0.97110.43830.87470.064*
H16B0.91680.26320.87990.064*
C170.8615 (6)0.4098 (8)0.9340 (2)0.0499 (16)
H17A0.84480.52380.93760.060*
H17B0.78290.35250.94190.060*
C180.9662 (7)0.3609 (9)0.9677 (3)0.0530 (17)
C190.9455 (6)0.3705 (8)1.0184 (3)0.0523 (17)
C201.0373 (8)0.3056 (10)1.0488 (3)0.067 (2)
H201.11150.25851.03660.080*
C211.0184 (10)0.3111 (10)1.0970 (3)0.078 (2)
H211.07950.26551.11700.093*
C220.9134 (9)0.3810 (9)1.1155 (3)0.069 (2)
H220.90230.38341.14810.083*
C230.8221 (8)0.4491 (8)1.0866 (3)0.0627 (19)
H230.74990.49901.09950.075*
C240.8381 (7)0.4431 (7)1.0385 (3)0.0552 (17)
H240.77570.48851.01910.066*
O60.5541 (7)0.3667 (8)0.2068 (3)0.103 (2)
H6A0.58430.36120.23460.154*
H6B0.60830.38160.18470.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0620 (3)0.0826 (4)0.0490 (3)0.0109 (3)0.0093 (4)0.0033 (4)
O10.049 (3)0.116 (5)0.070 (4)0.016 (3)0.001 (3)0.001 (3)
O20.048 (3)0.137 (6)0.069 (4)0.013 (4)0.004 (3)0.006 (3)
O30.111 (6)0.090 (4)0.075 (5)0.006 (4)0.011 (4)0.003 (4)
O40.112 (6)0.113 (6)0.161 (7)0.001 (5)0.064 (6)0.027 (5)
O50.079 (4)0.083 (4)0.130 (6)0.009 (3)0.025 (4)0.005 (3)
N10.061 (4)0.053 (4)0.048 (3)0.009 (3)0.003 (3)0.001 (3)
N20.051 (4)0.049 (3)0.041 (3)0.001 (3)0.002 (3)0.001 (3)
N30.059 (4)0.055 (4)0.053 (4)0.001 (3)0.001 (3)0.001 (3)
N40.057 (3)0.047 (3)0.044 (3)0.003 (3)0.005 (3)0.001 (3)
N50.078 (5)0.051 (4)0.069 (5)0.004 (3)0.012 (4)0.004 (3)
C10.080 (6)0.050 (4)0.066 (6)0.002 (4)0.008 (4)0.005 (4)
C20.064 (5)0.069 (5)0.061 (5)0.009 (4)0.011 (4)0.003 (4)
C30.059 (5)0.056 (4)0.044 (4)0.003 (4)0.007 (3)0.003 (3)
C40.047 (4)0.064 (5)0.053 (4)0.006 (3)0.006 (3)0.003 (3)
C50.047 (4)0.048 (4)0.053 (4)0.001 (3)0.003 (3)0.005 (3)
C60.041 (4)0.068 (5)0.055 (4)0.008 (3)0.005 (3)0.002 (3)
C70.041 (4)0.050 (4)0.059 (4)0.006 (3)0.003 (3)0.000 (3)
C80.050 (4)0.065 (5)0.058 (4)0.003 (3)0.003 (3)0.000 (3)
C90.063 (5)0.070 (5)0.062 (5)0.011 (4)0.005 (4)0.017 (4)
C100.089 (6)0.070 (5)0.056 (5)0.023 (5)0.001 (5)0.002 (4)
C110.087 (7)0.091 (7)0.057 (5)0.003 (5)0.018 (4)0.008 (4)
C120.066 (6)0.073 (5)0.070 (6)0.008 (4)0.013 (4)0.006 (4)
C130.054 (5)0.054 (4)0.047 (5)0.012 (4)0.003 (4)0.004 (3)
C140.101 (6)0.044 (4)0.061 (5)0.003 (4)0.025 (4)0.005 (3)
C150.089 (7)0.064 (5)0.052 (5)0.022 (4)0.015 (4)0.001 (4)
C160.050 (4)0.058 (4)0.052 (4)0.007 (3)0.000 (3)0.002 (3)
C170.045 (4)0.064 (4)0.041 (4)0.002 (3)0.003 (3)0.002 (3)
C180.046 (4)0.054 (4)0.059 (4)0.003 (3)0.004 (3)0.002 (3)
C190.049 (5)0.048 (3)0.060 (4)0.007 (3)0.006 (3)0.001 (3)
C200.057 (5)0.078 (5)0.065 (5)0.001 (4)0.015 (4)0.010 (4)
C210.093 (6)0.077 (6)0.063 (6)0.006 (5)0.026 (5)0.007 (4)
C220.094 (6)0.062 (5)0.052 (4)0.010 (5)0.003 (4)0.006 (4)
C230.074 (5)0.061 (5)0.053 (4)0.004 (4)0.001 (4)0.006 (3)
C240.054 (4)0.048 (4)0.064 (5)0.001 (3)0.004 (3)0.002 (3)
O60.115 (6)0.094 (4)0.098 (5)0.019 (4)0.031 (4)0.001 (4)
Geometric parameters (Å, º) top
Ag1—N12.084 (5)C9—C101.369 (11)
Ag1—N32.085 (6)C9—H90.9300
O1—C181.225 (9)C10—C111.393 (13)
O2—C61.214 (9)C10—H100.9300
O3—N51.250 (9)C11—C121.342 (13)
O4—N51.219 (9)C11—H110.9300
O5—N51.204 (9)C12—H120.9300
N1—C31.302 (9)C13—H130.9300
N1—C21.381 (9)C14—C151.332 (11)
N2—C31.335 (9)C14—H140.9300
N2—C11.358 (9)C15—H150.9300
N2—C41.453 (9)C16—C171.505 (9)
N3—C131.306 (9)C16—H16A0.9700
N3—C141.387 (9)C16—H16B0.9700
N4—C131.322 (8)C17—C181.502 (9)
N4—C151.359 (9)C17—H17A0.9700
N4—C161.461 (9)C17—H17B0.9700
C1—C21.336 (10)C18—C191.455 (10)
C1—H10.9300C19—C241.390 (9)
C2—H20.9300C19—C201.392 (10)
C3—H30.9300C20—C211.382 (13)
C4—C51.491 (9)C20—H200.9300
C4—H4A0.9700C21—C221.340 (12)
C4—H4B0.9700C21—H210.9300
C5—C61.493 (10)C22—C231.374 (11)
C5—H5A0.9700C22—H220.9300
C5—H5B0.9700C23—C241.374 (10)
C6—C71.466 (10)C23—H230.9300
C7—C121.391 (11)C24—H240.9300
C7—C81.392 (9)O6—H6A0.8499
C8—C91.372 (10)O6—H6B0.8499
C8—H80.9300
N1—Ag1—N3173.7 (2)C11—C10—H10120.6
C3—N1—C2105.2 (6)C12—C11—C10120.6 (8)
C3—N1—Ag1131.3 (5)C12—C11—H11119.7
C2—N1—Ag1123.4 (5)C10—C11—H11119.7
C3—N2—C1106.4 (6)C11—C12—C7121.9 (8)
C3—N2—C4126.7 (6)C11—C12—H12119.1
C1—N2—C4126.9 (6)C7—C12—H12119.1
C13—N3—C14105.7 (6)N3—C13—N4111.8 (6)
C13—N3—Ag1129.0 (5)N3—C13—H13124.1
C14—N3—Ag1124.5 (5)N4—C13—H13124.1
C13—N4—C15106.7 (6)C15—C14—N3108.0 (7)
C13—N4—C16127.5 (6)C15—C14—H14126.0
C15—N4—C16125.8 (6)N3—C14—H14126.0
O5—N5—O4121.9 (9)C14—C15—N4107.8 (7)
O5—N5—O3119.5 (8)C14—C15—H15126.1
O4—N5—O3118.5 (10)N4—C15—H15126.1
C2—C1—N2107.3 (7)N4—C16—C17111.7 (6)
C2—C1—H1126.4N4—C16—H16A109.3
N2—C1—H1126.4C17—C16—H16A109.3
C1—C2—N1109.0 (7)N4—C16—H16B109.3
C1—C2—H2125.5C17—C16—H16B109.3
N1—C2—H2125.5H16A—C16—H16B107.9
N1—C3—N2112.2 (6)C18—C17—C16112.8 (6)
N1—C3—H3123.9C18—C17—H17A109.0
N2—C3—H3123.9C16—C17—H17A109.0
N2—C4—C5111.9 (6)C18—C17—H17B109.0
N2—C4—H4A109.2C16—C17—H17B109.0
C5—C4—H4A109.2H17A—C17—H17B107.8
N2—C4—H4B109.2O1—C18—C19120.4 (7)
C5—C4—H4B109.2O1—C18—C17119.1 (7)
H4A—C4—H4B107.9C19—C18—C17120.5 (6)
C4—C5—C6113.6 (6)C24—C19—C20117.4 (7)
C4—C5—H5A108.8C24—C19—C18123.3 (7)
C6—C5—H5A108.8C20—C19—C18119.3 (7)
C4—C5—H5B108.8C21—C20—C19120.2 (8)
C6—C5—H5B108.8C21—C20—H20119.9
H5A—C5—H5B107.7C19—C20—H20119.9
O2—C6—C7120.7 (7)C22—C21—C20121.1 (8)
O2—C6—C5118.4 (7)C22—C21—H21119.4
C7—C6—C5120.9 (6)C20—C21—H21119.4
C12—C7—C8117.1 (7)C21—C22—C23120.3 (8)
C12—C7—C6119.3 (7)C21—C22—H22119.9
C8—C7—C6123.6 (6)C23—C22—H22119.9
C9—C8—C7121.2 (7)C24—C23—C22119.6 (7)
C9—C8—H8119.4C24—C23—H23120.2
C7—C8—H8119.4C22—C23—H23120.2
C10—C9—C8120.3 (7)C23—C24—C19121.4 (7)
C10—C9—H9119.8C23—C24—H24119.3
C8—C9—H9119.8C19—C24—H24119.3
C9—C10—C11118.9 (8)H6A—O6—H6B116.6
C9—C10—H10120.6
C3—N2—C1—C21.2 (9)C14—N3—C13—N41.0 (8)
C4—N2—C1—C2178.2 (7)Ag1—N3—C13—N4168.5 (5)
N2—C1—C2—N11.8 (9)C15—N4—C13—N31.6 (9)
C3—N1—C2—C11.7 (9)C16—N4—C13—N3178.1 (6)
Ag1—N1—C2—C1178.4 (5)C13—N3—C14—C150.1 (9)
C2—N1—C3—N20.9 (9)Ag1—N3—C14—C15170.1 (5)
Ag1—N1—C3—N2177.3 (4)N3—C14—C15—N40.9 (9)
C1—N2—C3—N10.1 (9)C13—N4—C15—C141.5 (9)
C4—N2—C3—N1177.2 (6)C16—N4—C15—C14178.1 (7)
C3—N2—C4—C5109.4 (8)C13—N4—C16—C1793.6 (8)
C1—N2—C4—C567.0 (9)C15—N4—C16—C1782.3 (9)
N2—C4—C5—C6173.6 (6)N4—C16—C17—C18176.7 (6)
C4—C5—C6—O20.8 (10)C16—C17—C18—O14.9 (10)
C4—C5—C6—C7178.5 (6)C16—C17—C18—C19174.2 (6)
O2—C6—C7—C128.7 (11)O1—C18—C19—C24172.2 (7)
C5—C6—C7—C12170.5 (6)C17—C18—C19—C248.7 (11)
O2—C6—C7—C8172.1 (7)O1—C18—C19—C207.3 (11)
C5—C6—C7—C88.7 (10)C17—C18—C19—C20171.9 (7)
C12—C7—C8—C90.2 (10)C24—C19—C20—C211.6 (11)
C6—C7—C8—C9179.4 (6)C18—C19—C20—C21178.9 (7)
C7—C8—C9—C100.5 (10)C19—C20—C21—C221.3 (13)
C8—C9—C10—C111.4 (11)C20—C21—C22—C230.1 (13)
C9—C10—C11—C121.7 (12)C21—C22—C23—C241.0 (11)
C10—C11—C12—C71.1 (12)C22—C23—C24—C190.6 (11)
C8—C7—C12—C110.1 (11)C20—C19—C24—C230.7 (10)
C6—C7—C12—C11179.1 (7)C18—C19—C24—C23179.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O5i0.852.263.036 (10)151
C4—H4B···O6ii0.972.563.384 (9)142
C5—H5B···O2i0.972.493.450 (9)169
C9—H9···O1iii0.932.563.331 (10)141
C16—H16A···O4iv0.972.503.299 (10)140
C22—H22···O3v0.932.593.514 (11)173
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y1/2, z+1/2; (iii) x+3/2, y1/2, z1/2; (iv) x+3/2, y+1/2, z+1/2; (v) x+1/2, y+1/2, z+1.
 

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