9-Oxo-4,5-diaza-fluoren-4-ium tetra-chloridoaurate(III)-4,5-diaza-fluoren-9-one (1/1).

The Au(III) atom in the title compound, (C(11)H(7)N(2)O)[AuCl(4)]·C(11)H(6)N(2)O, is in a nearly square-planar environment defined by four Cl atoms. The protonated 9-oxo-4,5-diaza-fluoren-4-ium cation forms an N-H⋯N hydrogen bond with the neutral 4,5-diaza-fluoren-9-one mol-ecule.

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 = 704.13

Triclinic,

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[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.067

S = 1.04

5044 reflections

302 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 3.05 e Å−3

Δρmin = −1.27 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C11H7N2O)[AuCl4]·C11H6N2O	Z = 2
Mr = 704.13	F(000) = 672
Triclinic, P1	Dx = 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

Bruker APEXII CCD diffractometer	5044 independent reflections
Radiation source: fine-focus sealed tube	4829 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.331, Tmax = 0.537	k = −16→16
9343 measured reflections	l = −17→17

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(Fo2) + (0.0509P)2 + 0.1124P] where P = (Fo2 + 2Fc2)/3
5044 reflections	(Δ/σ)max = 0.001
302 parameters	Δρmax = 3.05 e Å−3
1 restraint	Δρmin = −1.27 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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)