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

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

doi:10.1107/S1600536809006734

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m344

doi:10.1107/S1600536809006734

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

Nasser Safari,^a Vahid Amani,^a Behrouz Notash ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 February 2009; accepted 24 February 2009; online 28 February 2009)

The Au^III 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

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

Crystal data

(C₁₁H₇N₂O)[AuCl₄]·C₁₁H₆N₂O
M_r = 704.13
Triclinic, $[P \overline 1]$
a = 7.1035 (1) Å
b = 12.6513 (2) Å
c = 13.2366 (2) Å
α = 73.285 (1)°
β = 78.410 (1)°
γ = 88.375 (1)°
V = 1115.51 (3) Å³
Z = 2
Mo Kα radiation
μ = 7.10 mm⁻¹
T = 118 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.331, T_max = 0.537 (expected range = 0.303–0.491)
9343 measured reflections
5044 independent reflections
4829 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.067
S = 1.04
5044 reflections
302 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 3.05 e Å⁻³
Δρ_min = −1.27 e Å⁻³

Table 1
Selected bond lengths (Å)

Au1—Cl1	2.2720 (8)
Au1—Cl2	2.2882 (8)
Au1—Cl3	2.2864 (8)
Au1—Cl4	2.2872 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3	0.89 (1)	1.88 (1)	2.762 (4)	168 (4)

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006734/hy2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006734/hy2184Isup2.hkl

checkCIF report

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).

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

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]·C₁₁H₆N₂O	Z = 2
M_r = 704.13	F(000) = 672
Triclinic, P1	D_x = 2.096 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1035 (1) Å	Cell parameters from 7741 reflections
b = 12.6513 (2) Å	θ = 2.7–28.4°
c = 13.2366 (2) Å	µ = 7.10 mm⁻¹
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 tube	4829 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.331, T_max = 0.537	k = −16→16
9343 measured reflections	l = −17→17

Refinement top

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0509P)² + 0.1124P] where P = (F_o² + 2F_c²)/3
5044 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 3.05 e Å⁻³
1 restraint	Δρ_min = −1.27 e Å⁻³

Crystal data top

(C₁₁H₇N₂O)[AuCl₄]·C₁₁H₆N₂O	γ = 88.375 (1)°
M_r = 704.13	V = 1115.51 (3) Å³
Triclinic, P1	Z = 2
a = 7.1035 (1) Å	Mo Kα radiation
b = 12.6513 (2) Å	µ = 7.10 mm⁻¹
c = 13.2366 (2) Å	T = 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)
T_min = 0.331, T_max = 0.537	R_int = 0.016
9343 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	1 restraint
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 3.05 e Å⁻³
5044 reflections	Δρ_min = −1.27 e Å⁻³
302 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Au1	0.298203 (14)	0.304054 (8)	0.394619 (8)	0.01445 (6)
Cl1	0.28189 (13)	0.32712 (7)	0.56013 (7)	0.02448 (17)
Cl2	0.31382 (13)	0.49176 (6)	0.32181 (7)	0.02314 (17)
Cl3	0.31133 (12)	0.28082 (6)	0.22834 (6)	0.01975 (16)
Cl4	0.28622 (13)	0.11653 (6)	0.46788 (7)	0.02373 (17)
O1	0.1850 (4)	0.3950 (2)	0.7782 (2)	0.0258 (5)
O2	0.3590 (4)	1.22613 (19)	0.9995 (2)	0.0239 (5)
N1	0.2353 (4)	0.7025 (2)	0.9069 (2)	0.0163 (5)
H1	0.247 (6)	0.7760 (9)	0.885 (3)	0.029 (11)*
N2	0.2032 (4)	0.7897 (2)	0.6684 (2)	0.0187 (5)
N3	0.3136 (4)	0.9265 (2)	0.8548 (2)	0.0156 (5)
N4	0.1257 (4)	0.8534 (2)	1.0949 (2)	0.0168 (5)
C1	0.2546 (5)	0.6495 (3)	1.0088 (3)	0.0186 (6)
H1A	0.2662	0.6912	1.0567	0.022*
C2	0.2576 (5)	0.5354 (3)	1.0441 (3)	0.0203 (6)
H2	0.2704	0.4994	1.1159	0.024*
C3	0.2420 (5)	0.4737 (3)	0.9747 (3)	0.0205 (6)
H3	0.2447	0.3954	0.9977	0.025*
C4	0.2222 (4)	0.5296 (3)	0.8712 (3)	0.0164 (6)
C5	0.2212 (4)	0.6449 (2)	0.8388 (2)	0.0153 (6)
C6	0.2012 (4)	0.4900 (3)	0.7772 (3)	0.0181 (6)
C7	0.1980 (5)	0.5922 (3)	0.6874 (3)	0.0182 (6)
C8	0.1879 (5)	0.6097 (3)	0.5801 (3)	0.0212 (7)
H8	0.1825	0.5501	0.5504	0.025*
C9	0.1863 (5)	0.7187 (3)	0.5186 (3)	0.0212 (7)
H9	0.1809	0.7349	0.4445	0.025*
C10	0.1924 (5)	0.8047 (3)	0.5642 (3)	0.0223 (7)
H10	0.1888	0.8781	0.5195	0.027*
C11	0.2057 (4)	0.6848 (3)	0.7249 (3)	0.0155 (6)
C12	0.3999 (4)	0.9788 (3)	0.7520 (3)	0.0181 (6)
H12	0.4178	0.9380	0.7009	0.022*
C13	0.4636 (4)	1.0882 (3)	0.7171 (3)	0.0180 (6)
H13	0.5212	1.1206	0.6436	0.022*
C14	0.4435 (4)	1.1511 (2)	0.7894 (3)	0.0176 (6)
H14	0.4858	1.2264	0.7675	0.021*
C15	0.3585 (4)	1.0977 (2)	0.8947 (3)	0.0154 (6)
C16	0.2951 (4)	0.9874 (2)	0.9225 (2)	0.0139 (6)
C17	0.3142 (4)	1.1372 (2)	0.9930 (3)	0.0165 (6)
C18	0.2124 (4)	1.0415 (2)	1.0813 (3)	0.0162 (6)
C19	0.1345 (4)	1.0290 (3)	1.1887 (3)	0.0181 (6)
H19	0.1383	1.0876	1.2200	0.022*
C20	0.0503 (4)	0.9262 (3)	1.2485 (3)	0.0199 (6)
H20	−0.0062	0.9133	1.3226	0.024*
C21	0.0490 (4)	0.8422 (3)	1.1996 (3)	0.0195 (6)
H21	−0.0094	0.7729	1.2426	0.023*
C22	0.2039 (4)	0.9522 (2)	1.0394 (2)	0.0143 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.01648 (8)	0.01391 (8)	0.01188 (8)	0.00013 (5)	−0.00036 (5)	−0.00370 (5)
Cl1	0.0377 (5)	0.0222 (4)	0.0142 (4)	0.0028 (3)	−0.0047 (3)	−0.0066 (3)
Cl2	0.0343 (4)	0.0151 (4)	0.0193 (4)	−0.0012 (3)	−0.0052 (3)	−0.0038 (3)
Cl3	0.0262 (4)	0.0187 (4)	0.0144 (4)	−0.0011 (3)	−0.0020 (3)	−0.0061 (3)
Cl4	0.0333 (4)	0.0151 (4)	0.0194 (4)	0.0019 (3)	−0.0005 (3)	−0.0030 (3)
O1	0.0391 (14)	0.0147 (11)	0.0241 (13)	−0.0037 (10)	−0.0044 (11)	−0.0072 (10)
O2	0.0348 (13)	0.0135 (11)	0.0251 (13)	0.0004 (9)	−0.0077 (11)	−0.0074 (10)
N1	0.0197 (12)	0.0112 (12)	0.0171 (13)	0.0000 (9)	−0.0020 (10)	−0.0038 (10)
N2	0.0205 (13)	0.0146 (12)	0.0195 (14)	−0.0029 (10)	−0.0032 (11)	−0.0030 (10)
N3	0.0171 (12)	0.0149 (12)	0.0136 (12)	−0.0002 (9)	−0.0016 (10)	−0.0033 (10)
N4	0.0180 (12)	0.0155 (12)	0.0162 (13)	−0.0018 (9)	−0.0016 (10)	−0.0048 (10)
C1	0.0229 (15)	0.0171 (14)	0.0161 (15)	−0.0012 (11)	−0.0014 (12)	−0.0068 (12)
C2	0.0255 (16)	0.0161 (15)	0.0177 (16)	0.0011 (12)	−0.0038 (13)	−0.0031 (12)
C3	0.0228 (16)	0.0151 (14)	0.0211 (16)	0.0004 (12)	−0.0026 (13)	−0.0024 (12)
C4	0.0178 (14)	0.0136 (14)	0.0189 (15)	−0.0004 (11)	−0.0024 (12)	−0.0071 (12)
C5	0.0146 (13)	0.0143 (14)	0.0164 (15)	−0.0007 (10)	0.0001 (11)	−0.0054 (12)
C6	0.0189 (14)	0.0171 (15)	0.0191 (15)	0.0002 (11)	−0.0012 (12)	−0.0081 (12)
C7	0.0190 (14)	0.0161 (14)	0.0199 (16)	0.0005 (11)	−0.0021 (12)	−0.0071 (12)
C8	0.0212 (15)	0.0241 (16)	0.0198 (16)	−0.0026 (12)	−0.0037 (13)	−0.0089 (13)
C9	0.0194 (15)	0.0265 (17)	0.0169 (16)	−0.0016 (12)	−0.0025 (12)	−0.0054 (13)
C10	0.0224 (16)	0.0218 (16)	0.0197 (17)	−0.0023 (12)	−0.0048 (13)	−0.0007 (13)
C11	0.0137 (13)	0.0137 (14)	0.0181 (15)	−0.0001 (10)	−0.0023 (11)	−0.0035 (12)
C12	0.0190 (14)	0.0188 (15)	0.0162 (15)	0.0008 (11)	−0.0023 (12)	−0.0056 (12)
C13	0.0184 (14)	0.0176 (14)	0.0141 (14)	−0.0006 (11)	−0.0007 (12)	−0.0002 (12)
C14	0.0169 (14)	0.0130 (13)	0.0214 (16)	−0.0009 (11)	−0.0040 (12)	−0.0024 (12)
C15	0.0156 (13)	0.0128 (13)	0.0177 (15)	0.0032 (10)	−0.0046 (12)	−0.0035 (12)
C16	0.0122 (13)	0.0133 (13)	0.0155 (14)	0.0014 (10)	−0.0027 (11)	−0.0032 (11)
C17	0.0178 (14)	0.0131 (13)	0.0190 (15)	0.0030 (11)	−0.0057 (12)	−0.0040 (12)
C18	0.0149 (13)	0.0157 (14)	0.0183 (15)	0.0011 (11)	−0.0043 (11)	−0.0049 (12)
C19	0.0193 (14)	0.0184 (14)	0.0193 (15)	0.0028 (11)	−0.0060 (12)	−0.0084 (12)
C20	0.0170 (14)	0.0270 (16)	0.0148 (15)	0.0024 (12)	−0.0009 (12)	−0.0064 (13)
C21	0.0181 (14)	0.0172 (14)	0.0206 (16)	−0.0011 (11)	−0.0021 (12)	−0.0025 (12)
C22	0.0120 (12)	0.0149 (13)	0.0165 (14)	0.0020 (10)	−0.0036 (11)	−0.0047 (11)

Geometric parameters (Å, º) top

Au1—Cl1	2.2720 (8)	C7—C8	1.389 (5)
Au1—Cl2	2.2882 (8)	C7—C11	1.405 (4)
Au1—Cl3	2.2864 (8)	C8—C9	1.386 (5)
Au1—Cl4	2.2872 (8)	C8—H8	0.9500
O1—C6	1.208 (4)	C9—C10	1.393 (5)
O2—C17	1.209 (4)	C9—H9	0.9500
N1—C5	1.331 (4)	C10—H10	0.9500
N1—C1	1.355 (4)	C12—C13	1.385 (4)
N1—H1	0.89 (1)	C12—H12	0.9500
N2—C11	1.325 (4)	C13—C14	1.396 (4)
N2—C10	1.355 (4)	C13—H13	0.9500
N3—C16	1.326 (4)	C14—C15	1.381 (4)
N3—C12	1.354 (4)	C14—H14	0.9500
N4—C22	1.326 (4)	C15—C16	1.400 (4)
N4—C21	1.352 (4)	C15—C17	1.498 (4)
C1—C2	1.384 (4)	C16—C22	1.493 (4)
C1—H1A	0.9500	C17—C18	1.500 (4)
C2—C3	1.387 (5)	C18—C19	1.382 (4)
C2—H2	0.9500	C18—C22	1.402 (4)
C3—C4	1.383 (5)	C19—C20	1.392 (4)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.397 (4)	C20—C21	1.396 (4)
C4—C6	1.503 (4)	C20—H20	0.9500
C5—C11	1.471 (4)	C21—H21	0.9500
C6—C7	1.486 (5)

Cl1—Au1—Cl3	179.43 (3)	N2—C10—C9	123.9 (3)
Cl1—Au1—Cl4	90.27 (3)	N2—C10—H10	118.1
Cl3—Au1—Cl4	89.73 (3)	C9—C10—H10	118.1
Cl1—Au1—Cl2	89.47 (3)	N2—C11—C7	126.7 (3)
Cl3—Au1—Cl2	90.55 (3)	N2—C11—C5	125.6 (3)
Cl4—Au1—Cl2	179.30 (3)	C7—C11—C5	107.7 (3)
C5—N1—C1	120.1 (3)	N3—C12—C13	123.8 (3)
C5—N1—H1	122 (3)	N3—C12—H12	118.1
C1—N1—H1	118 (3)	C13—C12—H12	118.1
C11—N2—C10	114.0 (3)	C12—C13—C14	120.3 (3)
C16—N3—C12	115.2 (3)	C12—C13—H13	119.8
C22—N4—C21	115.0 (3)	C14—C13—H13	119.8
N1—C1—C2	120.9 (3)	C15—C14—C13	116.1 (3)
N1—C1—H1A	119.6	C15—C14—H14	121.9
C2—C1—H1A	119.6	C13—C14—H14	121.9
C1—C2—C3	120.1 (3)	C14—C15—C16	119.8 (3)
C1—C2—H2	120.0	C14—C15—C17	131.3 (3)
C3—C2—H2	120.0	C16—C15—C17	108.9 (3)
C4—C3—C2	118.0 (3)	N3—C16—C15	124.8 (3)
C4—C3—H3	121.0	N3—C16—C22	126.9 (3)
C2—C3—H3	121.0	C15—C16—C22	108.3 (3)
C3—C4—C5	120.0 (3)	O2—C17—C15	126.5 (3)
C3—C4—C6	132.0 (3)	O2—C17—C18	128.0 (3)
C5—C4—C6	107.9 (3)	C15—C17—C18	105.4 (2)
N1—C5—C4	121.0 (3)	C19—C18—C22	119.4 (3)
N1—C5—C11	129.2 (3)	C19—C18—C17	132.1 (3)
C4—C5—C11	109.8 (3)	C22—C18—C17	108.5 (3)
O1—C6—C7	128.9 (3)	C18—C19—C20	116.5 (3)
O1—C6—C4	126.0 (3)	C18—C19—H19	121.8
C7—C6—C4	105.1 (3)	C20—C19—H19	121.8
C8—C7—C11	118.2 (3)	C19—C20—C21	120.0 (3)
C8—C7—C6	132.5 (3)	C19—C20—H20	120.0
C11—C7—C6	109.4 (3)	C21—C20—H20	120.0
C9—C8—C7	116.6 (3)	N4—C21—C20	124.0 (3)
C9—C8—H8	121.7	N4—C21—H21	118.0
C7—C8—H8	121.7	C20—C21—H21	118.0
C8—C9—C10	120.7 (3)	N4—C22—C18	125.2 (3)
C8—C9—H9	119.7	N4—C22—C16	126.0 (3)
C10—C9—H9	119.7	C18—C22—C16	108.8 (3)

C5—N1—C1—C2	−0.8 (5)	C16—N3—C12—C13	−0.8 (5)
N1—C1—C2—C3	0.4 (5)	N3—C12—C13—C14	1.0 (5)
C1—C2—C3—C4	−0.4 (5)	C12—C13—C14—C15	0.1 (5)
C2—C3—C4—C5	0.9 (5)	C13—C14—C15—C16	−1.3 (4)
C2—C3—C4—C6	−179.7 (3)	C13—C14—C15—C17	179.7 (3)
C1—N1—C5—C4	1.2 (5)	C12—N3—C16—C15	−0.5 (4)
C1—N1—C5—C11	−177.8 (3)	C12—N3—C16—C22	179.1 (3)
C3—C4—C5—N1	−1.3 (5)	C14—C15—C16—N3	1.5 (5)
C6—C4—C5—N1	179.2 (3)	C17—C15—C16—N3	−179.3 (3)
C3—C4—C5—C11	177.9 (3)	C14—C15—C16—C22	−178.0 (3)
C6—C4—C5—C11	−1.6 (3)	C17—C15—C16—C22	1.2 (3)
C3—C4—C6—O1	5.2 (6)	C14—C15—C17—O2	−5.5 (6)
C5—C4—C6—O1	−175.3 (3)	C16—C15—C17—O2	175.4 (3)
C3—C4—C6—C7	−176.8 (3)	C14—C15—C17—C18	177.2 (3)
C5—C4—C6—C7	2.8 (3)	C16—C15—C17—C18	−1.9 (3)
O1—C6—C7—C8	−4.5 (6)	O2—C17—C18—C19	3.9 (6)
C4—C6—C7—C8	177.6 (4)	C15—C17—C18—C19	−178.8 (3)
O1—C6—C7—C11	175.0 (3)	O2—C17—C18—C22	−175.3 (3)
C4—C6—C7—C11	−2.9 (3)	C15—C17—C18—C22	2.0 (3)
C11—C7—C8—C9	0.0 (5)	C22—C18—C19—C20	−0.3 (4)
C6—C7—C8—C9	179.4 (3)	C17—C18—C19—C20	−179.5 (3)
C7—C8—C9—C10	−0.7 (5)	C18—C19—C20—C21	0.4 (5)
C11—N2—C10—C9	−0.6 (5)	C22—N4—C21—C20	−0.4 (5)
C8—C9—C10—N2	1.0 (5)	C19—C20—C21—N4	−0.1 (5)
C10—N2—C11—C7	−0.2 (5)	C21—N4—C22—C18	0.5 (4)
C10—N2—C11—C5	178.5 (3)	C21—N4—C22—C16	−178.9 (3)
C8—C7—C11—N2	0.5 (5)	C19—C18—C22—N4	−0.1 (5)
C6—C7—C11—N2	−179.1 (3)	C17—C18—C22—N4	179.2 (3)
C8—C7—C11—C5	−178.4 (3)	C19—C18—C22—C16	179.3 (3)
C6—C7—C11—C5	2.0 (4)	C17—C18—C22—C16	−1.3 (3)
N1—C5—C11—N2	0.0 (5)	N3—C16—C22—N4	0.0 (5)
C4—C5—C11—N2	−179.1 (3)	C15—C16—C22—N4	179.5 (3)
N1—C5—C11—C7	178.9 (3)	N3—C16—C22—C18	−179.5 (3)
C4—C5—C11—C7	−0.2 (4)	C15—C16—C22—C18	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.89 (1)	1.88 (1)	2.762 (4)	168 (4)

Experimental details

Crystal data
Chemical formula	(C₁₁H₇N₂O)[AuCl₄]·C₁₁H₆N₂O
M_r	704.13
Crystal system, space group	Triclinic, P1
Temperature (K)	118
a, b, c (Å)	7.1035 (1), 12.6513 (2), 13.2366 (2)
α, β, γ (°)	73.285 (1), 78.410 (1), 88.375 (1)
V (Å³)	1115.51 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.10
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.331, 0.537
No. of measured, independent and observed [I > 2σ(I)] reflections	9343, 5044, 4829
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.067, 1.04
No. of reflections	5044
No. of parameters	302
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	3.05, −1.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Au1—Cl1	2.2720 (8)	Au1—Cl3	2.2864 (8)
Au1—Cl2	2.2882 (8)	Au1—Cl4	2.2872 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.89 (1)	1.88 (1)	2.762 (4)	168 (4)

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Zhang, R.-L., Liu, H.-M., Zhao, J.-S., Gu, A.-P., He, S.-Y., Liu, J.-N. & Shi, Q.-Z. (2003). Chin. J. Inorg. Chem. 19, 722–726. CAS Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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