Literature DB >> 21583734

2,9-Dimethyl-4,7-diphenyl-1,10-phenanthrolin-1-ium tetra-chloridoaurate(III).

Sema Öztürk Yıldırım, Mehmet Akkurt, Nasser Safari, Anita Abedi, Vahid Amani, Vickie McKee.

Abstract

Both the cation and anion of the title compound, (C(26)H(21)N(2))[AuCl(4)], are disposed about a plane of mirror symmetry. The 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolinium ring is oriented at a dihedral angle of 44.2 (1)° with respect to the planar phenyl ring systems. The Au(III) atom has a square-planar environment defined by four Cl atoms. The crystal structure is stabilized by C-H⋯π and Au⋯π ring-metal (3.551 Å) inter-actions. In the crystal structure, the mol-ecules stack along the c axis via N-H⋯N hydrogen-bond inter-actions.

Entities: CellLine Chemical Disease Species

Year: 2009 PMID： 21583734 PMCID： PMC2977548 DOI： 10.1107/S1600536809011994

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background to proton-transfer systems and their structures, see: Abedi et al. (2008 ▶); Amani et al. (2008 ▶); Calleja et al. (2001 ▶); Hasan et al. (1999 ▶); Hojjat Kashani et al. (2008 ▶); Johnson & Steed (1998 ▶); Karaca et al. (2009 ▶); Yap et al. (1995 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

(C26H21N2)[AuCl4] M = 700.22 Orthorhombic, a = 13.5195 (10) Å b = 22.9565 (17) Å c = 7.5556 (6) Å V = 2345.0 (3) Å3 Z = 4 Mo Kα radiation μ = 6.75 mm−1 T = 150 K 0.20 × 0.06 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.345, T max = 0.774 24337 measured reflections 3265 independent reflections 2835 reflections with I > 2σ(I) R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.023 wR(F 2) = 0.054 S = 1.03 3265 reflections 159 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.85 e Å−3 Δρmin = −0.60 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011994/hg2496sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011994/hg2496Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C₂₆H₂₁N₂)[AuCl₄]	F(000) = 1352
M_r = 700.22	D_x = 1.983 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2n	Cell parameters from 5918 reflections
a = 13.5195 (10) Å	θ = 2.8–27.6°
b = 22.9565 (17) Å	µ = 6.75 mm⁻¹
c = 7.5556 (6) Å	T = 150 K
V = 2345.0 (3) Å³	Prism, yellow
Z = 4	0.20 × 0.06 × 0.04 mm

Bruker APEXII CCD diffractometer	3265 independent reflections
Radiation source: sealed tube	2835 reflections with I > 2σ(I)
graphite	R_int = 0.046
φ and ω scans	θ_max = 29.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −18→18
T_min = 0.345, T_max = 0.774	k = −31→31
24337 measured reflections	l = −10→10

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.026P)² + 1.1102P] where P = (F_o² + 2F_c²)/3
3265 reflections	(Δ/σ)_max = 0.001
159 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.51546 (16)	0.19238 (10)	0.0058 (3)	0.0203 (7)
C1	0.61127 (19)	0.10789 (13)	−0.0819 (4)	0.0271 (8)
C2	0.52022 (19)	0.13465 (11)	−0.0049 (3)	0.0202 (8)
C3	0.4389 (2)	0.10119 (12)	0.0488 (4)	0.0219 (8)
C4	0.3533 (2)	0.12606 (12)	0.1132 (3)	0.0200 (7)
C5	0.35028 (19)	0.18757 (11)	0.1303 (3)	0.0181 (7)
C6	0.43300 (19)	0.21879 (11)	0.0701 (3)	0.0190 (7)
C7	0.27048 (18)	0.22031 (10)	0.2068 (3)	0.0182 (7)
C8	0.26628 (19)	0.08820 (11)	0.1485 (3)	0.0199 (7)
C9	0.2791 (2)	0.03400 (11)	0.2301 (4)	0.0237 (8)
C10	0.2004 (2)	−0.00427 (12)	0.2445 (4)	0.0272 (8)
C11	0.1082 (2)	0.01067 (13)	0.1803 (4)	0.0279 (8)
C12	0.0937 (2)	0.06484 (13)	0.1013 (4)	0.0263 (8)
C13	0.1724 (2)	0.10337 (12)	0.0840 (3)	0.0230 (8)
Au1	0.38322 (1)	0.25000	0.60223 (2)	0.0219 (1)
Cl1	0.53754 (7)	0.25000	0.48086 (15)	0.0343 (3)
Cl2	0.38270 (5)	0.15042 (4)	0.60263 (10)	0.0336 (2)
Cl3	0.22961 (7)	0.25000	0.72842 (14)	0.0298 (3)
HN1	0.556 (4)	0.212 (2)	−0.029 (7)	0.009 (14)*	0.500
H1A	0.59680	0.09310	−0.19790	0.0410*
H1B	0.63310	0.07660	−0.00740	0.0410*
H1C	0.66240	0.13680	−0.08990	0.0410*
H3	0.44280	0.06080	0.04060	0.0260*
H7	0.21760	0.20050	0.25760	0.0220*
H9	0.34070	0.02370	0.27490	0.0280*
H10	0.20980	−0.04040	0.29790	0.0330*
H11	0.05590	−0.01540	0.18980	0.0340*
H12	0.03130	0.07520	0.06010	0.0310*
H13	0.16280	0.13930	0.02960	0.0280*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0164 (11)	0.0215 (11)	0.0230 (12)	−0.0001 (9)	0.0006 (9)	0.0006 (9)
C1	0.0232 (14)	0.0249 (14)	0.0333 (16)	0.0047 (11)	0.0024 (12)	−0.0025 (12)
C2	0.0215 (13)	0.0200 (13)	0.0191 (13)	0.0039 (10)	−0.0020 (10)	−0.0022 (10)
C3	0.0242 (14)	0.0194 (13)	0.0220 (13)	0.0028 (10)	−0.0005 (10)	−0.0008 (10)
C4	0.0204 (12)	0.0205 (12)	0.0192 (12)	−0.0002 (10)	−0.0012 (10)	0.0019 (10)
C5	0.0176 (11)	0.0199 (12)	0.0167 (12)	0.0000 (10)	−0.0030 (9)	0.0014 (9)
C6	0.0186 (12)	0.0205 (13)	0.0180 (12)	0.0000 (10)	−0.0032 (9)	0.0014 (10)
C7	0.0174 (11)	0.0204 (12)	0.0168 (12)	−0.0035 (9)	0.0008 (9)	−0.0002 (10)
C8	0.0207 (12)	0.0198 (12)	0.0193 (12)	−0.0009 (10)	0.0004 (10)	−0.0022 (10)
C9	0.0226 (12)	0.0229 (13)	0.0256 (14)	0.0033 (10)	0.0005 (11)	0.0017 (11)
C10	0.0325 (15)	0.0208 (13)	0.0284 (15)	0.0018 (11)	0.0057 (12)	0.0040 (11)
C11	0.0292 (14)	0.0266 (14)	0.0280 (15)	−0.0071 (12)	0.0058 (12)	−0.0028 (12)
C12	0.0218 (13)	0.0292 (15)	0.0278 (14)	0.0010 (11)	−0.0015 (11)	−0.0031 (12)
C13	0.0246 (14)	0.0210 (13)	0.0233 (13)	0.0025 (10)	−0.0018 (11)	−0.0004 (10)
Au1	0.0177 (1)	0.0292 (1)	0.0187 (1)	0.0000	−0.0022 (1)	0.0000
Cl1	0.0186 (4)	0.0474 (6)	0.0370 (6)	0.0000	0.0020 (4)	0.0000
Cl2	0.0326 (4)	0.0297 (4)	0.0386 (4)	0.0049 (3)	0.0006 (3)	0.0074 (3)
Cl3	0.0212 (4)	0.0383 (6)	0.0298 (5)	0.0000	0.0043 (4)	0.0000

Au1—Cl2ⁱ	2.2860 (9)	C8—C13	1.404 (4)
Au1—Cl3	2.2852 (10)	C8—C9	1.399 (4)
Au1—Cl1	2.2790 (10)	C9—C10	1.384 (4)
Au1—Cl2	2.2860 (9)	C10—C11	1.381 (4)
N1—C2	1.329 (3)	C11—C12	1.393 (4)
N1—C6	1.359 (3)	C12—C13	1.390 (4)
N1—HN1	0.76 (5)	C1—H1B	0.9600
C1—C2	1.494 (4)	C1—H1C	0.9600
C2—C3	1.401 (4)	C1—H1A	0.9600
C3—C4	1.379 (4)	C3—H3	0.9300
C4—C5	1.419 (4)	C7—H7	0.9300
C4—C8	1.487 (4)	C9—H9	0.9300
C5—C6	1.404 (4)	C10—H10	0.9300
C5—C7	1.436 (3)	C11—H11	0.9300
C6—C6ⁱ	1.433 (4)	C12—H12	0.9300
C7—C7ⁱ	1.363 (3)	C13—H13	0.9300

Au1···C7ⁱ	3.423 (2)	C13···C7	3.135 (4)
Au1···C7	3.423 (2)	C3···H10^xii	3.1000
Cl1···Cl3ⁱⁱ	3.4011 (15)	C3···H9	2.8000
Cl1···C7ⁱⁱⁱ	3.520 (3)	C5···H13	2.8700
Cl1···Cl2	3.2333 (11)	C7···H13	2.7100
Cl1···C6	3.485 (3)	C8···H10^xii	2.8900
Cl1···Cl3^iv	3.4011 (15)	C8···H7	2.7900
Cl1···C7^v	3.520 (3)	C9···H3	2.7100
Cl1···Cl2ⁱ	3.2333 (11)	C9···H1B^ix	3.0400
Cl1···C6ⁱ	3.485 (3)	C10···H1B^ix	2.8700
Cl2···Cl1	3.2333 (11)	C11···H1B^ix	2.9200
Cl2···C3^vi	3.636 (3)	C13···H10^xii	3.0500
Cl2···Cl3	3.2269 (11)	C13···H7	2.6600
Cl2···C2^vi	3.519 (2)	HN1···Cl3ⁱⁱⁱ	2.92 (5)
Cl3···Cl1^vii	3.4011 (15)	HN1···H1C	2.2900
Cl3···Cl2	3.2269 (11)	HN1···Cl3^v	2.92 (5)
Cl3···Cl1^viii	3.4011 (15)	HN1···N1ⁱ	2.28 (5)
Cl3···Cl2ⁱ	3.2269 (11)	H1B···C11ⁱⁱⁱ	2.9200
Cl1···H13^v	3.0500	H1B···C10ⁱⁱⁱ	2.8700
Cl1···H13ⁱⁱⁱ	3.0500	H1B···C9ⁱⁱⁱ	3.0400
Cl2···H12ⁱⁱⁱ	2.9200	H1C···HN1	2.2900
Cl2···H1C^ix	3.0000	H1C···Cl3^v	2.9500
Cl3···HN1^x	2.92 (5)	H1C···Cl2ⁱⁱⁱ	3.0000
Cl3···HN1^ix	2.92 (5)	H1C···Cl3ⁱⁱⁱ	2.9500
Cl3···H1C^x	2.9500	H3···H9	2.4000
Cl3···H1C^ix	2.9500	H3···C9	2.7100
N1···N1ⁱ	2.646 (3)	H7···C13	2.6600
N1···HN1ⁱ	2.28 (5)	H7···C8	2.7900
C2···C12ⁱⁱⁱ	3.585 (4)	H7···H13	2.3400
C2···Cl2^xi	3.519 (2)	H9···H3	2.4000
C3···C12ⁱⁱⁱ	3.474 (4)	H9···C3	2.8000
C3···Cl2^xi	3.636 (3)	H10···C13^xiii	3.0500
C6···Cl1	3.485 (3)	H10···C3^xiii	3.1000
C6···Cl1	3.485 (3)	H10···C8^xiii	2.8900
C7···C13	3.135 (4)	H12···Cl2^ix	2.9200
C7···Au1	3.423 (2)	H13···C7	2.7100
C7···Au1	3.423 (2)	H13···H7	2.3400
C7···Cl1^ix	3.520 (3)	H13···Cl1^x	3.0500
C7···Cl1^x	3.520 (3)	H13···Cl1^ix	3.0500
C12···C3^ix	3.474 (4)	H13···C5	2.8700
C12···C2^ix	3.585 (4)

Cl1—Au1—Cl3	179.07 (4)	C8—C9—C10	120.3 (3)
Cl1—Au1—Cl2ⁱ	90.19 (2)	C9—C10—C11	120.6 (3)
Cl2—Au1—Cl3	89.81 (2)	C10—C11—C12	120.0 (3)
Cl2—Au1—Cl2ⁱ	179.62 (3)	C11—C12—C13	120.0 (3)
Cl2ⁱ—Au1—Cl3	89.81 (2)	C8—C13—C12	120.1 (2)
Cl1—Au1—Cl2	90.19 (2)	H1A—C1—H1C	109.00
C2—N1—C6	120.4 (2)	C2—C1—H1A	109.00
C6—N1—HN1	117 (4)	C2—C1—H1B	109.00
C2—N1—HN1	123 (4)	C2—C1—H1C	109.00
C1—C2—C3	122.3 (2)	H1A—C1—H1B	109.00
N1—C2—C3	119.4 (2)	H1B—C1—H1C	109.00
N1—C2—C1	118.3 (2)	C2—C3—H3	119.00
C2—C3—C4	122.3 (3)	C4—C3—H3	119.00
C3—C4—C8	119.0 (2)	C7ⁱ—C7—H7	119.00
C5—C4—C8	122.9 (2)	C5—C7—H7	119.00
C3—C4—C5	117.9 (2)	C8—C9—H9	120.00
C6—C5—C7	117.5 (2)	C10—C9—H9	120.00
C4—C5—C7	125.4 (2)	C9—C10—H10	120.00
C4—C5—C6	117.1 (2)	C11—C10—H10	120.00
C5—C6—C6ⁱ	120.7 (2)	C12—C11—H11	120.00
N1—C6—C6ⁱ	116.5 (2)	C10—C11—H11	120.00
N1—C6—C5	122.8 (2)	C11—C12—H12	120.00
C5—C7—C7ⁱ	121.6 (2)	C13—C12—H12	120.00
C4—C8—C13	120.6 (2)	C12—C13—H13	120.00
C9—C8—C13	119.1 (2)	C8—C13—H13	120.00
C4—C8—C9	120.1 (2)

C6—N1—C2—C1	178.1 (2)	C7—C5—C6—N1	175.7 (2)
C6—N1—C2—C3	0.8 (4)	C7—C5—C6—C6ⁱ	−5.8 (3)
C2—N1—C6—C5	1.0 (4)	C4—C5—C7—C7ⁱ	−175.3 (2)
C2—N1—C6—C6ⁱ	−177.6 (2)	C6—C5—C7—C7ⁱ	5.9 (3)
N1—C2—C3—C4	−0.1 (4)	N1—C6—C6ⁱ—N1ⁱ	0.0 (3)
C1—C2—C3—C4	−177.3 (3)	N1—C6—C6ⁱ—C5ⁱ	178.6 (2)
C2—C3—C4—C5	−2.2 (4)	C5—C6—C6ⁱ—N1ⁱ	−178.6 (2)
C2—C3—C4—C8	173.2 (2)	C5—C6—C6ⁱ—C5ⁱ	0.0 (4)
C3—C4—C5—C6	3.7 (3)	C5—C7—C7ⁱ—C5ⁱ	0.0 (4)
C3—C4—C5—C7	−175.1 (2)	C4—C8—C9—C10	−172.4 (2)
C8—C4—C5—C6	−171.5 (2)	C13—C8—C9—C10	0.9 (4)
C8—C4—C5—C7	9.6 (4)	C4—C8—C13—C12	173.2 (2)
C3—C4—C8—C9	42.3 (3)	C9—C8—C13—C12	−0.1 (4)
C3—C4—C8—C13	−130.8 (3)	C8—C9—C10—C11	−0.6 (4)
C5—C4—C8—C9	−142.5 (3)	C9—C10—C11—C12	−0.4 (5)
C5—C4—C8—C13	44.4 (3)	C10—C11—C12—C13	1.3 (4)
C4—C5—C6—N1	−3.2 (3)	C11—C12—C13—C8	−1.0 (4)
C4—C5—C6—C6ⁱ	175.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···N1ⁱ	0.76 (5)	2.28 (5)	2.646 (3)	111 (4)
C1—H1B···Cg3ⁱⁱⁱ	0.96	2.76	3.574 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯N1ⁱ	0.76 (5)	2.28 (5)	2.646 (3)	111 (4)
C1—H1B⋯Cg3ⁱⁱ	0.96	2.76	3.574 (3)	143

Symmetry codes: (i) ; (ii) . Cg3 is the centroid of the C8–C13 ring.

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