Bis(4-acetyl­anilinium) tetra­chloro­cuprate(II)

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.

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

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Computing details

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)

Crystal data

(C8H10NO)2[CuCl4]	F(000) = 1944
Mr = 477.68	Dx = 1.514 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2bc 2	Cell parameters from 25 reflections
a = 19.7316 (11) Å	θ = 9.8–14.2°
b = 15.3962 (9) Å	µ = 1.56 mm^−1
c = 13.8017 (8) Å	T = 293 K
V = 4193 (1) Å^3	Plate, dark brown
Z = 8	0.25 × 0.23 × 0.22 mm

Data collection

Nonius MACH3 sealed-tube diffractometer	1464 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω–2θ scans	h = −23→14
Absorption correction: ψ scan (North et al., 1968)	k = −14→18
Tmin = 0.671, Tmax = 0.739	l = −1→16
4121 measured reflections	3 standard reflections every 60 min
1904 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0554P)^2 + 5.7534P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1904 reflections	Δρmax = 0.55 e Å^−3
120 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00068 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.22369 (17)	0.46818 (18)	0.8719 (2)	0.0345 (7)
C11	0.17181 (18)	0.5390 (2)	0.8650 (2)	0.0406 (7)
C12	0.09913 (18)	0.5183 (2)	0.8488 (3)	0.0546 (9)
H12A	0.0815	0.4882	0.9042	0.082*
H12B	0.0947	0.4822	0.7924	0.082*
H12C	0.0742	0.5712	0.8392	0.082*
O11	0.19089 (13)	0.61397 (14)	0.8734 (2)	0.0603 (7)
C2	0.20477 (17)	0.38100 (19)	0.8717 (2)	0.0414 (8)
H2	0.1594	0.3658	0.8650	0.050*
C3	0.25364 (17)	0.31682 (19)	0.8816 (2)	0.0424 (8)
H3	0.2414	0.2585	0.8811	0.051*
C4	0.32045 (16)	0.34058 (18)	0.8920 (2)	0.0363 (7)
N41	0.37222 (14)	0.27333 (16)	0.9056 (2)	0.0451 (7)
H41A	0.4076	0.2847	0.8677	0.068*
H41B	0.3550	0.2218	0.8900	0.068*
H41C	0.3854	0.2727	0.9673	0.068*
C5	0.34070 (17)	0.42677 (19)	0.8914 (2)	0.0402 (8)
H5	0.3861	0.4418	0.8977	0.048*
C6	0.29128 (17)	0.48949 (19)	0.8811 (2)	0.0396 (8)
H6	0.3039	0.5477	0.8802	0.048*
Cu	0.0000	0.25382 (4)	0.85996 (4)	0.0411 (2)
Cl1	0.0000	0.32741 (8)	0.99849 (9)	0.0499 (3)
Cl2	0.0000	0.33273 (8)	0.71727 (9)	0.0528 (3)
Cl3	0.10209 (4)	0.19301 (6)	0.85990 (8)	0.0588 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0387 (16)	0.0298 (14)	0.0350 (16)	0.0000 (12)	−0.0004 (13)	−0.0022 (12)
C11	0.0478 (19)	0.0378 (16)	0.0362 (16)	0.0038 (14)	−0.0006 (15)	−0.0035 (13)
C12	0.041 (2)	0.0471 (19)	0.076 (3)	0.0056 (15)	−0.0001 (18)	−0.0073 (18)
O11	0.0584 (17)	0.0309 (12)	0.091 (2)	0.0034 (11)	−0.0067 (15)	−0.0018 (12)
C2	0.0315 (17)	0.0376 (16)	0.055 (2)	−0.0051 (13)	−0.0006 (15)	0.0014 (14)
C3	0.0380 (18)	0.0290 (14)	0.060 (2)	−0.0041 (13)	0.0006 (16)	0.0034 (14)
C4	0.0356 (17)	0.0330 (15)	0.0402 (16)	0.0004 (13)	−0.0027 (14)	0.0021 (13)
N41	0.0360 (16)	0.0366 (13)	0.0626 (18)	0.0005 (11)	−0.0041 (13)	0.0046 (13)
C5	0.0342 (18)	0.0372 (16)	0.0491 (18)	−0.0077 (13)	−0.0054 (14)	0.0000 (14)
C6	0.0452 (19)	0.0282 (14)	0.0456 (18)	−0.0052 (13)	−0.0024 (14)	−0.0013 (13)
Cu	0.0270 (3)	0.0500 (4)	0.0464 (4)	0.000	0.000	−0.0062 (3)
Cl1	0.0507 (7)	0.0495 (7)	0.0495 (7)	0.000	0.000	−0.0103 (5)
Cl2	0.0499 (7)	0.0621 (8)	0.0465 (7)	0.000	0.000	0.0011 (6)
Cl3	0.0348 (5)	0.0600 (5)	0.0815 (7)	0.0112 (4)	−0.0041 (4)	−0.0153 (5)

Geometric parameters (Å, º)

C1—C6	1.379 (5)	C4—C5	1.386 (4)
C1—C2	1.393 (4)	C4—N41	1.466 (4)
C1—C11	1.498 (4)	N41—H41A	0.8900
C11—O11	1.220 (4)	N41—H41B	0.8900
C11—C12	1.486 (5)	N41—H41C	0.8900
C12—H12A	0.9600	C5—C6	1.380 (4)
C12—H12B	0.9600	C5—H5	0.9300
C12—H12C	0.9600	C6—H6	0.9300
C2—C3	1.387 (4)	Cu—Cl3^i	2.2213 (9)
C2—H2	0.9300	Cu—Cl3	2.2213 (9)
C3—C4	1.376 (4)	Cu—Cl1	2.2223 (13)
C3—H3	0.9300	Cu—Cl2	2.3139 (14)
C6—C1—C2	119.2 (3)	C5—C4—N41	118.4 (3)
C6—C1—C11	119.6 (3)	C4—N41—H41A	109.5
C2—C1—C11	121.2 (3)	C4—N41—H41B	109.5
O11—C11—C12	121.0 (3)	H41A—N41—H41B	109.5
O11—C11—C1	118.1 (3)	C4—N41—H41C	109.5
C12—C11—C1	120.9 (3)	H41A—N41—H41C	109.5
C11—C12—H12A	109.5	H41B—N41—H41C	109.5
C11—C12—H12B	109.5	C6—C5—C4	117.9 (3)
H12A—C12—H12B	109.5	C6—C5—H5	121.1
C11—C12—H12C	109.5	C4—C5—H5	121.1
H12A—C12—H12C	109.5	C1—C6—C5	121.8 (3)
H12B—C12—H12C	109.5	C1—C6—H6	119.1
C3—C2—C1	120.0 (3)	C5—C6—H6	119.1
C3—C2—H2	120.0	Cl3^i—Cu—Cl3	130.14 (6)
C1—C2—H2	120.0	Cl3^i—Cu—Cl1	102.43 (3)
C4—C3—C2	119.1 (3)	Cl3—Cu—Cl1	102.43 (3)
C4—C3—H3	120.4	Cl3^i—Cu—Cl2	102.77 (3)
C2—C3—H3	120.4	Cl3—Cu—Cl2	102.77 (3)
C3—C4—C5	122.0 (3)	Cl1—Cu—Cl2	117.68 (5)
C3—C4—N41	119.5 (3)
C6—C1—C11—O11	−4.2 (4)	C2—C3—C4—C5	−1.1 (5)
C2—C1—C11—O11	174.1 (3)	C2—C3—C4—N41	178.1 (3)
C6—C1—C11—C12	176.1 (3)	C3—C4—C5—C6	0.8 (5)
C2—C1—C11—C12	−5.6 (4)	N41—C4—C5—C6	−178.4 (3)
C6—C1—C2—C3	0.6 (5)	C2—C1—C6—C5	−0.9 (5)
C11—C1—C2—C3	−177.8 (3)	C11—C1—C6—C5	177.5 (3)
C1—C2—C3—C4	0.4 (5)	C4—C5—C6—C1	0.2 (5)

Symmetry code: (i) −x, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N41—H41A···Cl2^ii	0.89	2.29	3.173 (3)	172
N41—H41B···O11^iii	0.89	1.90	2.787 (3)	171
N41—H41C···Cl3^iv	0.89	2.46	3.317 (3)	163

Symmetry codes: (ii) x+1/2, y, −z+3/2; (iii) −x+1/2, y−1/2, z; (iv) −x+1/2, −y+1/2, −z+2.