supplementary materials


Acta Cryst. (2009). E65, m344    [ doi:10.1107/S1600536809006734 ]

9-Oxo-4,5-diazafluoren-4-ium tetrachloridoaurate(III)-4,5-diazafluoren-9-one (1/1)

N. Safari, V. Amani, B. Notash and S. W. Ng

Abstract top

The AuIII atom in the title compound, (C11H7N2O)[AuCl4]·C11H6N2O, is in a nearly square-planar environment defined by four Cl atoms. The protonated 9-oxo-4,5-diazafluoren-4-ium cation forms an N-H...N hydrogen bond with the neutral 4,5-diazafluoren-9-one molecule.

Related literature top

For other 9-oxo-4,5-diazafluoren-4-ium tetrachloridometallates, see: Kulkarni et al. (2003); Menon et al. (1994); Ravikumar et al. (1995); Ravikumar & Lakshmi (1994); Zhang et al. (2003). For the synthesis of 4,5-diazafluoren-9-one, see: Henderson et al. (1984).

Experimental top

Chloroauric acid trihydrate (0.25 g, 0.73 mmol) dissolved in acetonitrile (5 ml) was mixed with 4,5-diazafluoren-9-one (Henderson et al., 1984) (0.13 g, 0.73 mmol) dissolved in methanol (5 ml). The yellow solution was set aside for the growth of crystals, which appeared after two weeks (yield 70%; m.p. 483 K).

Refinement top

C-bound H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.95 Å and with Uiso(H) = 1.2Ueq(C). The N-bound H atom was located in a difference Fourier map and refined isotropically, with a distance restraint of N—H = 0.88 (1) Å. The crystal diffracted strongly owing to the extremely heavy metal atom; however, its presence introduced severe absorption problems that could not be corrected analytically as the crystal did not have regular faces. The final difference Fourier map had a highest peak at 1.00 Å and a deepest hole at 1.00 Å from Au1 atom.

Computing details top

Data collection: APEX2 (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 70% probability level. The dashed line denotes hydrogen bond.
9-Oxo-4,5-diazafluoren-4-ium tetrachloridoaurate(III)–4,5-diazafluoren-9-one (1/1) top
Crystal data top
(C11H7N2O)[AuCl4]·C11H6N2OZ = 2
Mr = 704.13F(000) = 672
Triclinic, P1Dx = 2.096 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1035 (1) ÅCell parameters from 7741 reflections
b = 12.6513 (2) Åθ = 2.7–28.4°
c = 13.2366 (2) ŵ = 7.10 mm1
α = 73.285 (1)°T = 118 K
β = 78.410 (1)°Block, yellow
γ = 88.375 (1)°0.20 × 0.10 × 0.10 mm
V = 1115.51 (3) Å3
Data collection top
Bruker APEXII CCD
diffractometer
5044 independent reflections
Radiation source: fine-focus sealed tube4829 reflections with I > 2σ(I)
graphiteRint = 0.016
φ and ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.331, Tmax = 0.537k = 1616
9343 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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.1124P]
where P = (Fo2 + 2Fc2)/3
5044 reflections(Δ/σ)max = 0.001
302 parametersΔρmax = 3.05 e Å3
1 restraintΔρmin = 1.27 e Å3
Crystal data top
(C11H7N2O)[AuCl4]·C11H6N2Oγ = 88.375 (1)°
Mr = 704.13V = 1115.51 (3) Å3
Triclinic, P1Z = 2
a = 7.1035 (1) ÅMo Kα radiation
b = 12.6513 (2) ŵ = 7.10 mm1
c = 13.2366 (2) ÅT = 118 K
α = 73.285 (1)°0.20 × 0.10 × 0.10 mm
β = 78.410 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
5044 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4829 reflections with I > 2σ(I)
Tmin = 0.331, Tmax = 0.537Rint = 0.016
9343 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.067Δρmax = 3.05 e Å3
S = 1.04Δρmin = 1.27 e Å3
5044 reflectionsAbsolute structure: ?
302 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Au10.298203 (14)0.304054 (8)0.394619 (8)0.01445 (6)
Cl10.28189 (13)0.32712 (7)0.56013 (7)0.02448 (17)
Cl20.31382 (13)0.49176 (6)0.32181 (7)0.02314 (17)
Cl30.31133 (12)0.28082 (6)0.22834 (6)0.01975 (16)
Cl40.28622 (13)0.11653 (6)0.46788 (7)0.02373 (17)
O10.1850 (4)0.3950 (2)0.7782 (2)0.0258 (5)
O20.3590 (4)1.22613 (19)0.9995 (2)0.0239 (5)
N10.2353 (4)0.7025 (2)0.9069 (2)0.0163 (5)
H10.247 (6)0.7760 (9)0.885 (3)0.029 (11)*
N20.2032 (4)0.7897 (2)0.6684 (2)0.0187 (5)
N30.3136 (4)0.9265 (2)0.8548 (2)0.0156 (5)
N40.1257 (4)0.8534 (2)1.0949 (2)0.0168 (5)
C10.2546 (5)0.6495 (3)1.0088 (3)0.0186 (6)
H1A0.26620.69121.05670.022*
C20.2576 (5)0.5354 (3)1.0441 (3)0.0203 (6)
H20.27040.49941.11590.024*
C30.2420 (5)0.4737 (3)0.9747 (3)0.0205 (6)
H30.24470.39540.99770.025*
C40.2222 (4)0.5296 (3)0.8712 (3)0.0164 (6)
C50.2212 (4)0.6449 (2)0.8388 (2)0.0153 (6)
C60.2012 (4)0.4900 (3)0.7772 (3)0.0181 (6)
C70.1980 (5)0.5922 (3)0.6874 (3)0.0182 (6)
C80.1879 (5)0.6097 (3)0.5801 (3)0.0212 (7)
H80.18250.55010.55040.025*
C90.1863 (5)0.7187 (3)0.5186 (3)0.0212 (7)
H90.18090.73490.44450.025*
C100.1924 (5)0.8047 (3)0.5642 (3)0.0223 (7)
H100.18880.87810.51950.027*
C110.2057 (4)0.6848 (3)0.7249 (3)0.0155 (6)
C120.3999 (4)0.9788 (3)0.7520 (3)0.0181 (6)
H120.41780.93800.70090.022*
C130.4636 (4)1.0882 (3)0.7171 (3)0.0180 (6)
H130.52121.12060.64360.022*
C140.4435 (4)1.1511 (2)0.7894 (3)0.0176 (6)
H140.48581.22640.76750.021*
C150.3585 (4)1.0977 (2)0.8947 (3)0.0154 (6)
C160.2951 (4)0.9874 (2)0.9225 (2)0.0139 (6)
C170.3142 (4)1.1372 (2)0.9930 (3)0.0165 (6)
C180.2124 (4)1.0415 (2)1.0813 (3)0.0162 (6)
C190.1345 (4)1.0290 (3)1.1887 (3)0.0181 (6)
H190.13831.08761.22000.022*
C200.0503 (4)0.9262 (3)1.2485 (3)0.0199 (6)
H200.00620.91331.32260.024*
C210.0490 (4)0.8422 (3)1.1996 (3)0.0195 (6)
H210.00940.77291.24260.023*
C220.2039 (4)0.9522 (2)1.0394 (2)0.0143 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.01648 (8)0.01391 (8)0.01188 (8)0.00013 (5)0.00036 (5)0.00370 (5)
Cl10.0377 (5)0.0222 (4)0.0142 (4)0.0028 (3)0.0047 (3)0.0066 (3)
Cl20.0343 (4)0.0151 (4)0.0193 (4)0.0012 (3)0.0052 (3)0.0038 (3)
Cl30.0262 (4)0.0187 (4)0.0144 (4)0.0011 (3)0.0020 (3)0.0061 (3)
Cl40.0333 (4)0.0151 (4)0.0194 (4)0.0019 (3)0.0005 (3)0.0030 (3)
O10.0391 (14)0.0147 (11)0.0241 (13)0.0037 (10)0.0044 (11)0.0072 (10)
O20.0348 (13)0.0135 (11)0.0251 (13)0.0004 (9)0.0077 (11)0.0074 (10)
N10.0197 (12)0.0112 (12)0.0171 (13)0.0000 (9)0.0020 (10)0.0038 (10)
N20.0205 (13)0.0146 (12)0.0195 (14)0.0029 (10)0.0032 (11)0.0030 (10)
N30.0171 (12)0.0149 (12)0.0136 (12)0.0002 (9)0.0016 (10)0.0033 (10)
N40.0180 (12)0.0155 (12)0.0162 (13)0.0018 (9)0.0016 (10)0.0048 (10)
C10.0229 (15)0.0171 (14)0.0161 (15)0.0012 (11)0.0014 (12)0.0068 (12)
C20.0255 (16)0.0161 (15)0.0177 (16)0.0011 (12)0.0038 (13)0.0031 (12)
C30.0228 (16)0.0151 (14)0.0211 (16)0.0004 (12)0.0026 (13)0.0024 (12)
C40.0178 (14)0.0136 (14)0.0189 (15)0.0004 (11)0.0024 (12)0.0071 (12)
C50.0146 (13)0.0143 (14)0.0164 (15)0.0007 (10)0.0001 (11)0.0054 (12)
C60.0189 (14)0.0171 (15)0.0191 (15)0.0002 (11)0.0012 (12)0.0081 (12)
C70.0190 (14)0.0161 (14)0.0199 (16)0.0005 (11)0.0021 (12)0.0071 (12)
C80.0212 (15)0.0241 (16)0.0198 (16)0.0026 (12)0.0037 (13)0.0089 (13)
C90.0194 (15)0.0265 (17)0.0169 (16)0.0016 (12)0.0025 (12)0.0054 (13)
C100.0224 (16)0.0218 (16)0.0197 (17)0.0023 (12)0.0048 (13)0.0007 (13)
C110.0137 (13)0.0137 (14)0.0181 (15)0.0001 (10)0.0023 (11)0.0035 (12)
C120.0190 (14)0.0188 (15)0.0162 (15)0.0008 (11)0.0023 (12)0.0056 (12)
C130.0184 (14)0.0176 (14)0.0141 (14)0.0006 (11)0.0007 (12)0.0002 (12)
C140.0169 (14)0.0130 (13)0.0214 (16)0.0009 (11)0.0040 (12)0.0024 (12)
C150.0156 (13)0.0128 (13)0.0177 (15)0.0032 (10)0.0046 (12)0.0035 (12)
C160.0122 (13)0.0133 (13)0.0155 (14)0.0014 (10)0.0027 (11)0.0032 (11)
C170.0178 (14)0.0131 (13)0.0190 (15)0.0030 (11)0.0057 (12)0.0040 (12)
C180.0149 (13)0.0157 (14)0.0183 (15)0.0011 (11)0.0043 (11)0.0049 (12)
C190.0193 (14)0.0184 (14)0.0193 (15)0.0028 (11)0.0060 (12)0.0084 (12)
C200.0170 (14)0.0270 (16)0.0148 (15)0.0024 (12)0.0009 (12)0.0064 (13)
C210.0181 (14)0.0172 (14)0.0206 (16)0.0011 (11)0.0021 (12)0.0025 (12)
C220.0120 (12)0.0149 (13)0.0165 (14)0.0020 (10)0.0036 (11)0.0047 (11)
Geometric parameters (Å, °) top
Au1—Cl12.2720 (8)C7—C81.389 (5)
Au1—Cl22.2882 (8)C7—C111.405 (4)
Au1—Cl32.2864 (8)C8—C91.386 (5)
Au1—Cl42.2872 (8)C8—H80.9500
O1—C61.208 (4)C9—C101.393 (5)
O2—C171.209 (4)C9—H90.9500
N1—C51.331 (4)C10—H100.9500
N1—C11.355 (4)C12—C131.385 (4)
N1—H10.89 (1)C12—H120.9500
N2—C111.325 (4)C13—C141.396 (4)
N2—C101.355 (4)C13—H130.9500
N3—C161.326 (4)C14—C151.381 (4)
N3—C121.354 (4)C14—H140.9500
N4—C221.326 (4)C15—C161.400 (4)
N4—C211.352 (4)C15—C171.498 (4)
C1—C21.384 (4)C16—C221.493 (4)
C1—H1A0.9500C17—C181.500 (4)
C2—C31.387 (5)C18—C191.382 (4)
C2—H20.9500C18—C221.402 (4)
C3—C41.383 (5)C19—C201.392 (4)
C3—H30.9500C19—H190.9500
C4—C51.397 (4)C20—C211.396 (4)
C4—C61.503 (4)C20—H200.9500
C5—C111.471 (4)C21—H210.9500
C6—C71.486 (5)
Cl1—Au1—Cl3179.43 (3)N2—C10—C9123.9 (3)
Cl1—Au1—Cl490.27 (3)N2—C10—H10118.1
Cl3—Au1—Cl489.73 (3)C9—C10—H10118.1
Cl1—Au1—Cl289.47 (3)N2—C11—C7126.7 (3)
Cl3—Au1—Cl290.55 (3)N2—C11—C5125.6 (3)
Cl4—Au1—Cl2179.30 (3)C7—C11—C5107.7 (3)
C5—N1—C1120.1 (3)N3—C12—C13123.8 (3)
C5—N1—H1122 (3)N3—C12—H12118.1
C1—N1—H1118 (3)C13—C12—H12118.1
C11—N2—C10114.0 (3)C12—C13—C14120.3 (3)
C16—N3—C12115.2 (3)C12—C13—H13119.8
C22—N4—C21115.0 (3)C14—C13—H13119.8
N1—C1—C2120.9 (3)C15—C14—C13116.1 (3)
N1—C1—H1A119.6C15—C14—H14121.9
C2—C1—H1A119.6C13—C14—H14121.9
C1—C2—C3120.1 (3)C14—C15—C16119.8 (3)
C1—C2—H2120.0C14—C15—C17131.3 (3)
C3—C2—H2120.0C16—C15—C17108.9 (3)
C4—C3—C2118.0 (3)N3—C16—C15124.8 (3)
C4—C3—H3121.0N3—C16—C22126.9 (3)
C2—C3—H3121.0C15—C16—C22108.3 (3)
C3—C4—C5120.0 (3)O2—C17—C15126.5 (3)
C3—C4—C6132.0 (3)O2—C17—C18128.0 (3)
C5—C4—C6107.9 (3)C15—C17—C18105.4 (2)
N1—C5—C4121.0 (3)C19—C18—C22119.4 (3)
N1—C5—C11129.2 (3)C19—C18—C17132.1 (3)
C4—C5—C11109.8 (3)C22—C18—C17108.5 (3)
O1—C6—C7128.9 (3)C18—C19—C20116.5 (3)
O1—C6—C4126.0 (3)C18—C19—H19121.8
C7—C6—C4105.1 (3)C20—C19—H19121.8
C8—C7—C11118.2 (3)C19—C20—C21120.0 (3)
C8—C7—C6132.5 (3)C19—C20—H20120.0
C11—C7—C6109.4 (3)C21—C20—H20120.0
C9—C8—C7116.6 (3)N4—C21—C20124.0 (3)
C9—C8—H8121.7N4—C21—H21118.0
C7—C8—H8121.7C20—C21—H21118.0
C8—C9—C10120.7 (3)N4—C22—C18125.2 (3)
C8—C9—H9119.7N4—C22—C16126.0 (3)
C10—C9—H9119.7C18—C22—C16108.8 (3)
C5—N1—C1—C20.8 (5)C16—N3—C12—C130.8 (5)
N1—C1—C2—C30.4 (5)N3—C12—C13—C141.0 (5)
C1—C2—C3—C40.4 (5)C12—C13—C14—C150.1 (5)
C2—C3—C4—C50.9 (5)C13—C14—C15—C161.3 (4)
C2—C3—C4—C6179.7 (3)C13—C14—C15—C17179.7 (3)
C1—N1—C5—C41.2 (5)C12—N3—C16—C150.5 (4)
C1—N1—C5—C11177.8 (3)C12—N3—C16—C22179.1 (3)
C3—C4—C5—N11.3 (5)C14—C15—C16—N31.5 (5)
C6—C4—C5—N1179.2 (3)C17—C15—C16—N3179.3 (3)
C3—C4—C5—C11177.9 (3)C14—C15—C16—C22178.0 (3)
C6—C4—C5—C111.6 (3)C17—C15—C16—C221.2 (3)
C3—C4—C6—O15.2 (6)C14—C15—C17—O25.5 (6)
C5—C4—C6—O1175.3 (3)C16—C15—C17—O2175.4 (3)
C3—C4—C6—C7176.8 (3)C14—C15—C17—C18177.2 (3)
C5—C4—C6—C72.8 (3)C16—C15—C17—C181.9 (3)
O1—C6—C7—C84.5 (6)O2—C17—C18—C193.9 (6)
C4—C6—C7—C8177.6 (4)C15—C17—C18—C19178.8 (3)
O1—C6—C7—C11175.0 (3)O2—C17—C18—C22175.3 (3)
C4—C6—C7—C112.9 (3)C15—C17—C18—C222.0 (3)
C11—C7—C8—C90.0 (5)C22—C18—C19—C200.3 (4)
C6—C7—C8—C9179.4 (3)C17—C18—C19—C20179.5 (3)
C7—C8—C9—C100.7 (5)C18—C19—C20—C210.4 (5)
C11—N2—C10—C90.6 (5)C22—N4—C21—C200.4 (5)
C8—C9—C10—N21.0 (5)C19—C20—C21—N40.1 (5)
C10—N2—C11—C70.2 (5)C21—N4—C22—C180.5 (4)
C10—N2—C11—C5178.5 (3)C21—N4—C22—C16178.9 (3)
C8—C7—C11—N20.5 (5)C19—C18—C22—N40.1 (5)
C6—C7—C11—N2179.1 (3)C17—C18—C22—N4179.2 (3)
C8—C7—C11—C5178.4 (3)C19—C18—C22—C16179.3 (3)
C6—C7—C11—C52.0 (4)C17—C18—C22—C161.3 (3)
N1—C5—C11—N20.0 (5)N3—C16—C22—N40.0 (5)
C4—C5—C11—N2179.1 (3)C15—C16—C22—N4179.5 (3)
N1—C5—C11—C7178.9 (3)N3—C16—C22—C18179.5 (3)
C4—C5—C11—C70.2 (4)C15—C16—C22—C180.1 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N30.89 (1)1.88 (1)2.762 (4)168 (4)
Table 1
Selected geometric parameters (Å)
top
Au1—Cl12.2720 (8)Au1—Cl32.2864 (8)
Au1—Cl22.2882 (8)Au1—Cl42.2872 (8)
Table 2
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
N1—H1···N30.89 (1)1.88 (1)2.762 (4)168 (4)
Acknowledgements top

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

references
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