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A new gold(III) complex of di-2-pyridylamine (DPA), [AuCl2(C19H9N3)]Cl, has been synthesized and characterized by ESI–MS, 1H NMR spectroscopy, elemental analysis and X-ray structural analysis. The compound possesses crystallographically imposed mirror symmetry. The DPA ligand coordinates to the gold(III) centre in a bidentate mode. The distance between the metal centre and the Cl anion is 3.037 (2) Å. The cations are linked into layers parallel to the bc plane through N—H...Cl and C—H...Cl hydrogen-bond inter­actions. The title complex is more cytotoxic than cisplatin against A-549 and HCT-116 tumour cell lines.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014255/rz2023sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014255/rz2023Isup2.hkl
Contains datablock I

CCDC reference: 611219

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.031
  • wR factor = 0.082
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Dichloro(di-2-pyridylamine)gold(III) chloride top
Crystal data top
[AuCl2(C10H9N3)]ClF(000) = 880
Mr = 474.52Dx = 2.488 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 3897 reflections
a = 12.549 (4) Åθ = 2.3–28.0°
b = 12.313 (4) ŵ = 12.22 mm1
c = 8.200 (2) ÅT = 273 K
V = 1267.0 (7) Å3Block, red
Z = 40.3 × 0.22 × 0.16 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1299 independent reflections
Radiation source: fine-focus sealed tube1238 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
φ and ω scansθmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1514
Tmin = 0.043, Tmax = 0.141k = 1513
6226 measured reflectionsl = 109
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)] = 0.031H-atom parameters constrained
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0442P)2 + 3.0733P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
1299 reflectionsΔρmax = 1.50 e Å3
83 parametersΔρmin = 1.61 e Å3
0 restraintsExtinction correction: SHELXTL (Bruker, 2000), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0010 (3)
Special details top

Experimental. Spectroscopic analysis: 1H NMR (CD3SOCD3, δ, p.p.m.): 8.71 (d, 2H, J = 6.3 Hz), 8.26 (t, 2H, J = 7.7 Hz), 7.60 (d, 2H, J = 8.3 Hz), 7.54 (t, 2H, J = 6.73 Hz). ESI–MS (+P) m/z = 438.1.

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
Au10.01457 (3)0.25000.79814 (3)0.02216 (17)
C10.0959 (4)0.3501 (5)0.5219 (6)0.0231 (11)
C20.1337 (5)0.4368 (5)0.4301 (7)0.0258 (12)
H20.14390.42910.31840.031*
C30.1556 (5)0.5327 (6)0.5041 (8)0.0340 (14)
H30.18130.59090.44340.041*
C40.1394 (5)0.5437 (5)0.6725 (8)0.0307 (14)
H40.15670.60800.72590.037*
C50.0978 (5)0.4580 (5)0.7559 (7)0.0291 (13)
H50.08530.46520.86720.035*
Cl10.12404 (13)0.12231 (13)0.90454 (19)0.0383 (4)
Cl20.1445 (2)0.25000.0773 (2)0.0397 (6)
N10.0739 (4)0.3627 (4)0.6822 (5)0.0216 (10)
N20.0787 (6)0.25000.4496 (8)0.0284 (16)
H2B0.11990.25000.35980.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.0196 (2)0.0282 (2)0.0187 (2)0.0000.00364 (10)0.000
C10.017 (3)0.030 (3)0.022 (2)0.006 (2)0.000 (2)0.000 (2)
C20.020 (3)0.033 (3)0.024 (3)0.003 (2)0.004 (2)0.004 (2)
C30.020 (3)0.039 (3)0.043 (4)0.000 (3)0.002 (3)0.010 (3)
C40.029 (4)0.027 (3)0.036 (3)0.003 (3)0.005 (3)0.001 (2)
C50.028 (3)0.035 (3)0.025 (3)0.003 (3)0.005 (3)0.007 (2)
Cl10.0358 (9)0.0430 (9)0.0360 (8)0.0094 (7)0.0116 (7)0.0051 (7)
Cl20.0456 (14)0.0499 (13)0.0235 (10)0.0000.0025 (9)0.000
N10.017 (2)0.028 (2)0.021 (2)0.001 (2)0.0027 (18)0.0026 (18)
N20.035 (4)0.029 (4)0.021 (3)0.0000.006 (3)0.000
Geometric parameters (Å, º) top
Au1—N1i2.015 (5)C2—H20.9300
Au1—N12.015 (5)C3—C41.403 (9)
Au1—Cl12.2628 (16)C3—H30.9300
Au1—Cl1i2.2628 (16)C4—C51.362 (9)
Au1—Cl2ii3.037 (2)C4—H40.9300
C1—N11.352 (7)C5—N11.354 (8)
C1—N21.385 (6)C5—H50.9300
C1—C21.390 (8)N2—C1i1.385 (6)
C2—C31.355 (9)N2—H2B0.9000
N1i—Au1—N187.0 (3)C2—C3—C4119.7 (6)
N1i—Au1—Cl192.18 (15)C2—C3—H3120.1
N1—Au1—Cl1174.11 (13)C4—C3—H3120.1
N1i—Au1—Cl1i174.11 (13)C5—C4—C3118.3 (6)
N1—Au1—Cl1i92.18 (15)C5—C4—H4120.8
Cl1—Au1—Cl1i88.02 (9)C3—C4—H4120.8
N1i—Au1—Cl2ii89.61 (14)N1—C5—C4122.2 (5)
N1—Au1—Cl2ii89.61 (14)N1—C5—H5118.9
Cl1—Au1—Cl2ii96.22 (6)C4—C5—H5118.9
Cl1i—Au1—Cl2ii96.22 (6)C5—N1—C1119.2 (5)
N1—C1—N2119.1 (5)C5—N1—Au1120.6 (4)
N1—C1—C2120.5 (5)C1—N1—Au1119.5 (4)
N2—C1—C2120.3 (5)C1—N2—C1i125.7 (6)
C3—C2—C1119.7 (5)C1—N2—H2B105.1
C3—C2—H2120.1C1i—N2—H2B105.1
C1—C2—H2120.1
N1—C1—C2—C34.5 (9)C2—C1—N1—Au1164.4 (4)
N2—C1—C2—C3176.5 (6)N1i—Au1—N1—C5145.9 (4)
C1—C2—C3—C40.3 (9)Cl1i—Au1—N1—C539.9 (5)
C2—C3—C4—C52.6 (10)Cl2ii—Au1—N1—C556.3 (4)
C3—C4—C5—N11.4 (10)N1i—Au1—N1—C144.1 (5)
C4—C5—N1—C12.7 (9)Cl1i—Au1—N1—C1130.0 (4)
C4—C5—N1—Au1167.3 (5)Cl2ii—Au1—N1—C1133.7 (4)
N2—C1—N1—C5175.4 (6)N1—C1—N2—C1i36.9 (12)
C2—C1—N1—C55.7 (8)C2—C1—N2—C1i144.1 (6)
N2—C1—N1—Au114.5 (8)
Symmetry codes: (i) x, y+1/2, z; (ii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···Cl20.902.343.162 (7)153
C5—H5···Cl1iii0.932.743.457 (6)135
Symmetry code: (iii) x, y+1/2, z+2.
 

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