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The title compound, (C8H10NO)2[CuCl4], crystallizes with one 4-acetyl­anilinium cation and one half of a tetra­chloro­cuprate(II) anion in the asymmetric unit as the anion lies about a mirror plane with the Cu atom and two Cl ligands lying in the mirror plane. The geometry around the copper(II) ion is that of a discrete flattened tetra­hedron. The cations are connected through N—H...O hydrogen bonds leading to a lamellar structure parallel to the ab plane. These sheets are also connected through the anions by N—H...Cl hydrogen bonds, leading to a three-dimensional hydrogen-bonded network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053323/sj2195sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053323/sj2195Isup2.hkl
Contains datablock I

CCDC reference: 634012

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.040
  • wR factor = 0.111
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 48.00 A   3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Bis(4-acetylanilinium) tetrachlorocuprate(II) top
Crystal data top
(C8H10NO)2[CuCl4]F(000) = 1944
Mr = 477.68Dx = 1.514 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2bc 2Cell parameters from 25 reflections
a = 19.7316 (11) Åθ = 9.8–14.2°
b = 15.3962 (9) ŵ = 1.56 mm1
c = 13.8017 (8) ÅT = 293 K
V = 4193 (1) Å3Plate, dark brown
Z = 80.25 × 0.23 × 0.22 mm
Data collection top
Nonius MACH3 sealed-tube
diffractometer
1464 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω–2θ scansh = 2314
Absorption correction: ψ scan
(North et al., 1968)
k = 1418
Tmin = 0.671, Tmax = 0.739l = 116
4121 measured reflections3 standard reflections every 60 min
1904 independent reflections intensity decay: none
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0554P)2 + 5.7534P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1904 reflectionsΔρmax = 0.55 e Å3
120 parametersΔρmin = 0.38 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00068 (11)
Special details top

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
C10.22369 (17)0.46818 (18)0.8719 (2)0.0345 (7)
C110.17181 (18)0.5390 (2)0.8650 (2)0.0406 (7)
C120.09913 (18)0.5183 (2)0.8488 (3)0.0546 (9)
H12A0.08150.48820.90420.082*
H12B0.09470.48220.79240.082*
H12C0.07420.57120.83920.082*
O110.19089 (13)0.61397 (14)0.8734 (2)0.0603 (7)
C20.20477 (17)0.38100 (19)0.8717 (2)0.0414 (8)
H20.15940.36580.86500.050*
C30.25364 (17)0.31682 (19)0.8816 (2)0.0424 (8)
H30.24140.25850.88110.051*
C40.32045 (16)0.34058 (18)0.8920 (2)0.0363 (7)
N410.37222 (14)0.27333 (16)0.9056 (2)0.0451 (7)
H41A0.40760.28470.86770.068*
H41B0.35500.22180.89000.068*
H41C0.38540.27270.96730.068*
C50.34070 (17)0.42677 (19)0.8914 (2)0.0402 (8)
H50.38610.44180.89770.048*
C60.29128 (17)0.48949 (19)0.8811 (2)0.0396 (8)
H60.30390.54770.88020.048*
Cu0.00000.25382 (4)0.85996 (4)0.0411 (2)
Cl10.00000.32741 (8)0.99849 (9)0.0499 (3)
Cl20.00000.33273 (8)0.71727 (9)0.0528 (3)
Cl30.10209 (4)0.19301 (6)0.85990 (8)0.0588 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0387 (16)0.0298 (14)0.0350 (16)0.0000 (12)0.0004 (13)0.0022 (12)
C110.0478 (19)0.0378 (16)0.0362 (16)0.0038 (14)0.0006 (15)0.0035 (13)
C120.041 (2)0.0471 (19)0.076 (3)0.0056 (15)0.0001 (18)0.0073 (18)
O110.0584 (17)0.0309 (12)0.091 (2)0.0034 (11)0.0067 (15)0.0018 (12)
C20.0315 (17)0.0376 (16)0.055 (2)0.0051 (13)0.0006 (15)0.0014 (14)
C30.0380 (18)0.0290 (14)0.060 (2)0.0041 (13)0.0006 (16)0.0034 (14)
C40.0356 (17)0.0330 (15)0.0402 (16)0.0004 (13)0.0027 (14)0.0021 (13)
N410.0360 (16)0.0366 (13)0.0626 (18)0.0005 (11)0.0041 (13)0.0046 (13)
C50.0342 (18)0.0372 (16)0.0491 (18)0.0077 (13)0.0054 (14)0.0000 (14)
C60.0452 (19)0.0282 (14)0.0456 (18)0.0052 (13)0.0024 (14)0.0013 (13)
Cu0.0270 (3)0.0500 (4)0.0464 (4)0.0000.0000.0062 (3)
Cl10.0507 (7)0.0495 (7)0.0495 (7)0.0000.0000.0103 (5)
Cl20.0499 (7)0.0621 (8)0.0465 (7)0.0000.0000.0011 (6)
Cl30.0348 (5)0.0600 (5)0.0815 (7)0.0112 (4)0.0041 (4)0.0153 (5)
Geometric parameters (Å, º) top
C1—C61.379 (5)C4—C51.386 (4)
C1—C21.393 (4)C4—N411.466 (4)
C1—C111.498 (4)N41—H41A0.8900
C11—O111.220 (4)N41—H41B0.8900
C11—C121.486 (5)N41—H41C0.8900
C12—H12A0.9600C5—C61.380 (4)
C12—H12B0.9600C5—H50.9300
C12—H12C0.9600C6—H60.9300
C2—C31.387 (4)Cu—Cl3i2.2213 (9)
C2—H20.9300Cu—Cl32.2213 (9)
C3—C41.376 (4)Cu—Cl12.2223 (13)
C3—H30.9300Cu—Cl22.3139 (14)
C6—C1—C2119.2 (3)C5—C4—N41118.4 (3)
C6—C1—C11119.6 (3)C4—N41—H41A109.5
C2—C1—C11121.2 (3)C4—N41—H41B109.5
O11—C11—C12121.0 (3)H41A—N41—H41B109.5
O11—C11—C1118.1 (3)C4—N41—H41C109.5
C12—C11—C1120.9 (3)H41A—N41—H41C109.5
C11—C12—H12A109.5H41B—N41—H41C109.5
C11—C12—H12B109.5C6—C5—C4117.9 (3)
H12A—C12—H12B109.5C6—C5—H5121.1
C11—C12—H12C109.5C4—C5—H5121.1
H12A—C12—H12C109.5C1—C6—C5121.8 (3)
H12B—C12—H12C109.5C1—C6—H6119.1
C3—C2—C1120.0 (3)C5—C6—H6119.1
C3—C2—H2120.0Cl3i—Cu—Cl3130.14 (6)
C1—C2—H2120.0Cl3i—Cu—Cl1102.43 (3)
C4—C3—C2119.1 (3)Cl3—Cu—Cl1102.43 (3)
C4—C3—H3120.4Cl3i—Cu—Cl2102.77 (3)
C2—C3—H3120.4Cl3—Cu—Cl2102.77 (3)
C3—C4—C5122.0 (3)Cl1—Cu—Cl2117.68 (5)
C3—C4—N41119.5 (3)
C6—C1—C11—O114.2 (4)C2—C3—C4—C51.1 (5)
C2—C1—C11—O11174.1 (3)C2—C3—C4—N41178.1 (3)
C6—C1—C11—C12176.1 (3)C3—C4—C5—C60.8 (5)
C2—C1—C11—C125.6 (4)N41—C4—C5—C6178.4 (3)
C6—C1—C2—C30.6 (5)C2—C1—C6—C50.9 (5)
C11—C1—C2—C3177.8 (3)C11—C1—C6—C5177.5 (3)
C1—C2—C3—C40.4 (5)C4—C5—C6—C10.2 (5)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N41—H41A···Cl2ii0.892.293.173 (3)172
N41—H41B···O11iii0.891.902.787 (3)171
N41—H41C···Cl3iv0.892.463.317 (3)163
Symmetry codes: (ii) x+1/2, y, z+3/2; (iii) x+1/2, y1/2, z; (iv) x+1/2, y+1/2, z+2.
 

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