The square-planar to flattened-tetrahedral CuX₄²⁻ (X = Cl, Br) structural phase transition in 1,2,6-trimethylpyridinium salts

The abrupt green-to-yellow thermochromism observed for certain A₂CuCl₄ compounds has long been attributed to the presence of strong N—H hydrogen bonding in the low-temperature phase that favors square-planar CuCl₄²⁻ (green in color) through reduction of ligand–ligand repulsion. Weakening of the hydrogen bonding at higher temperature results in the transformation to (far more common) flattened-tetrahedral geometry – the expected geometry for CuBr₄²⁻ complexes due to their greater ligand–ligand repulsion. The square-planar to flattened-tetrahedral transitions in (1,2,6-trimethylpyridinium)₂CuX₄ provide the first examples of this phase transformation in the absence of N—H hydrogen bonding and for a CuBr₄²⁻ complex. These results suggest that the square-planar to flattened-tetrahedral transformation in CuX₄²⁻ systems may be more common than previously thought.

Computing details

Data collection: Collect (Nonius BV, 1997-2000) for Cl100K; Collect (Bruker AXS BV, 1997-2004) for Cl295K, Cl350K, Br100K, Br295K, 26lutcl100k, 26lutclrt, 26lutbr100k, 26lutbrrt, 26lut100kortho, 26lutrtortho, 123tmpcubr4, nmphcucl4. For all compounds, cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997). Program(s) used to solve structure: SIR92 (Giacovazzo et al., 1993) for 26lut100kortho; SHELXS86 (Sheldrick, 1986) for 26lutrtortho; SIR92 (Altomare et al., 1994) for 123tmpcubr4, nmphcucl4. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) for Cl100K, Cl295K, Cl350K, Br100K, Br295K, 26lutcl100k, 26lutclrt, 26lutbr100k, 26lutbrrt, 26lut100kortho, 26lutrtortho; ORTEP for Windows (Farrugia, 2012) for 123tmpcubr4, nmphcucl4. Software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) for Cl100K, Cl295K, Cl350K, Br100K, Br295K, 26lutcl100k, 26lutclrt, 26lutbr100k, 26lutbrrt, 26lut100kortho, 26lutrtortho; WinGX publication routines (Farrugia, 2012) for 123tmpcubr4, nmphcucl4.

Figures

(Cl100K) bis(1,2,6-trimethylpyridinium) tetrachloridocuprate(II)

Crystal data

2(C8H12N)·Cl4Cu	F(000) = 462
Mr = 449.74	Dx = 1.601 Mg m^−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
a = 12.9074 (4) Å	Cell parameters from 2151 reflections
b = 9.2262 (4) Å	θ = 2.9–35.0°
c = 8.6377 (3) Å	µ = 1.74 mm^−1
β = 114.925 (2)°	T = 100 K
V = 932.82 (6) Å^3	Block, dark green
Z = 2	0.21 × 0.18 × 0.12 mm

Data collection

KappaCCD diffractometer	2151 independent reflections
Radiation source: Enraf Nonius FR590	1935 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 9 pixels mm^-1	θmax = 35.0°, θmin = 3.4°
CCD rotation images, thick slices scans	h = 0→20
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = 0→14
Tmin = 0.674, Tmax = 0.787	l = −13→12
15464 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	All H-atom parameters refined
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0283P)^2 + 0.6906P] where P = (Fo^2 + 2Fc^2)/3
2151 reflections	(Δ/σ)max < 0.001
80 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.68 e Å^−3

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	Occ. (<1)
Cu1	0	0	0	0.01213 (6)
Cl1	0.06870 (3)	0	0.28688 (4)	0.01716 (7)
Cl2	0	0.24919 (4)	0	0.01781 (7)
N1	0.16689 (10)	0.5	0.69761 (15)	0.0150 (2)
C11	0.19794 (16)	0.5	0.8827 (2)	0.0252 (3)
H11A	0.2039	0.5981	0.9227	0.038*	0.25
H11B	0.27	0.4518	0.9415	0.038*	0.25
H11C	0.1402	0.4501	0.9045	0.038*	0.25
H11D	0.2054	0.4019	0.9231	0.038*	0.25
H11E	0.1394	0.5482	0.9042	0.038*	0.25
H11F	0.2692	0.5499	0.9413	0.038*	0.25
C2	0.15386 (8)	0.37049 (11)	0.61484 (13)	0.01470 (16)
C21	0.16974 (10)	0.23177 (12)	0.71163 (15)	0.02023 (19)
C3	0.12551 (9)	0.37025 (11)	0.44109 (13)	0.01543 (16)
C4	0.11144 (12)	0.5	0.35383 (18)	0.0162 (2)
H21A	0.1204 (15)	0.2267 (19)	0.772 (2)	0.028 (4)*
H21B	0.2497 (15)	0.2252 (19)	0.799 (2)	0.028 (4)*
H21C	0.1529 (15)	0.150 (2)	0.636 (2)	0.030 (5)*
H3	0.1164 (14)	0.2761 (19)	0.384 (2)	0.021 (4)*
H4	0.0930 (18)	0.5	0.234 (3)	0.017 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01340 (10)	0.01157 (10)	0.01138 (10)	0	0.00518 (8)	0
Cl1	0.02395 (16)	0.01313 (13)	0.01228 (13)	0	0.00556 (11)	0
Cl2	0.02771 (17)	0.01185 (13)	0.01307 (13)	0	0.00783 (12)	0
N1	0.0168 (5)	0.0160 (5)	0.0133 (5)	0	0.0073 (4)	0
C11	0.0342 (8)	0.0284 (8)	0.0138 (6)	0	0.0110 (6)	0
C2	0.0143 (4)	0.0140 (4)	0.0164 (4)	−0.0003 (3)	0.0070 (3)	0.0008 (3)
C21	0.0237 (5)	0.0169 (4)	0.0221 (4)	0.0012 (4)	0.0116 (4)	0.0044 (4)
C3	0.0163 (4)	0.0147 (4)	0.0152 (4)	−0.0008 (3)	0.0065 (3)	−0.0010 (3)
C4	0.0165 (6)	0.0172 (6)	0.0140 (5)	0	0.0054 (4)	0

Geometric parameters (Å, º)

Cu1—Cl1	2.2527 (3)	C11—H11F	0.96
Cu1—Cl2	2.2990 (3)	C2—C3	1.3868 (14)
N1—C2	1.3660 (11)	C2—C21	1.4949 (14)
N1—C11	1.4755 (19)	C21—H21A	0.982 (17)
C11—H11A	0.96	C21—H21B	0.992 (18)
C11—H11B	0.96	C21—H21C	0.963 (19)
C11—H11C	0.96	C3—C4	1.3852 (12)
C11—H11D	0.96	C3—H3	0.979 (17)
C11—H11E	0.96	C4—H4	0.96 (2)
C2—N1—C2^i	122.03 (12)	H11B—C11—H11F	56.3
C2—N1—C11	118.98 (6)	H11C—C11—H11F	141.1
C2^i—N1—C11	118.98 (6)	H11D—C11—H11F	109.5
N1—C11—H11A	109.5	H11E—C11—H11F	109.5
N1—C11—H11B	109.5	N1—C2—C3	119.07 (9)
H11A—C11—H11B	109.5	N1—C2—C21	119.91 (9)
N1—C11—H11C	109.5	C3—C2—C21	121.02 (9)
H11A—C11—H11C	109.5	C2—C21—H21A	111.9 (10)
H11B—C11—H11C	109.5	C2—C21—H21B	109.5 (10)
N1—C11—H11D	109.5	H21A—C21—H21B	106.8 (15)
H11A—C11—H11D	141.1	C2—C21—H21C	110.5 (11)
H11B—C11—H11D	56.3	H21A—C21—H21C	108.4 (15)
H11C—C11—H11D	56.3	H21B—C21—H21C	109.7 (15)
N1—C11—H11E	109.5	C4—C3—C2	120.12 (10)
H11A—C11—H11E	56.3	C4—C3—H3	122.3 (10)
H11B—C11—H11E	141.1	C2—C3—H3	117.6 (10)
H11C—C11—H11E	56.3	C3—C4—C3^i	119.58 (13)
H11D—C11—H11E	109.5	C3—C4—H4^i	120.21 (7)
N1—C11—H11F	109.5	C3—C4—H4	120.21 (7)
H11A—C11—H11F	56.3

Symmetry code: (i) x, −y+1, z.

(Cl295K) bis(1,2,6-trimethylpyridinium) tetrachloridocuprate(II)

Crystal data

2(C8H12N)·Cl4Cu	F(000) = 462
Mr = 449.74	Dx = 1.550 Mg m^−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 2673 reflections
a = 13.1910 (6) Å	θ = 0.4–37.8°
b = 9.2068 (4) Å	µ = 1.69 mm^−1
c = 8.7242 (4) Å	T = 295 K
β = 114.595 (2)°	Irregular, dark green
V = 963.40 (7) Å^3	0.30 × 0.27 × 0.11 mm
Z = 2

Data collection

KappaCCD diffractometer	2683 independent reflections
Radiation source: Enraf Nonius FR590	2199 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 9 pixels mm^-1	θmax = 37.8°, θmin = 3.4°
CCD rotation images, thick slices scans	h = −22→22
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −15→15
Tmin = 0.605, Tmax = 0.679	l = −14→14
16662 measured reflections

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)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 0.5819P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2683 reflections	Δρmax = 0.97 e Å^−3
63 parameters	Δρmin = −0.65 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.051 (4)
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
Cu1	0	0	0	0.03164 (11)
Cl1	0.07072 (6)	0	0.28351 (6)	0.05048 (15)
Cl2	0	0.24890 (6)	0	0.05661 (17)
N1	0.16613 (14)	0.5	0.6966 (2)	0.0376 (3)
C11	0.1975 (3)	0.5	0.8794 (3)	0.0604 (7)
H11A	0.2035	0.5983	0.919	0.091*	0.25
H11B	0.2679	0.4518	0.9361	0.091*	0.25
H11C	0.1416	0.4499	0.9025	0.091*	0.25
H11D	0.2052	0.4017	0.9194	0.091*	0.25
H11E	0.1407	0.5482	0.9023	0.091*	0.25
H11F	0.2671	0.5501	0.9359	0.091*	0.25
C2	0.15287 (12)	0.37061 (15)	0.61426 (19)	0.0382 (3)
C21	0.16918 (17)	0.2315 (2)	0.7094 (3)	0.0563 (4)
H21A	0.2452	0.2245	0.7907	0.084*
H21B	0.1521	0.1513	0.6324	0.084*
H21C	0.1207	0.2293	0.7664	0.084*
C3	0.12391 (13)	0.37090 (16)	0.4430 (2)	0.0420 (3)
H3	0.1142	0.2834	0.3854	0.05*
C4	0.10934 (19)	0.5	0.3569 (3)	0.0438 (4)
H4	0.0898	0.5	0.2414	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.03373 (16)	0.02926 (15)	0.03201 (15)	0	0.01377 (11)	0
Cl1	0.0733 (4)	0.0350 (2)	0.0333 (2)	0	0.0124 (2)	0
Cl2	0.0968 (5)	0.0306 (2)	0.0389 (2)	0	0.0248 (3)	0
N1	0.0381 (7)	0.0408 (8)	0.0358 (7)	0	0.0173 (6)	0
C11	0.0739 (17)	0.0729 (18)	0.0357 (10)	0	0.0240 (11)	0
C2	0.0376 (6)	0.0357 (6)	0.0433 (6)	−0.0001 (4)	0.0191 (5)	0.0031 (5)
C21	0.0663 (10)	0.0439 (8)	0.0648 (10)	0.0045 (7)	0.0333 (9)	0.0140 (8)
C3	0.0441 (6)	0.0384 (7)	0.0429 (7)	−0.0030 (5)	0.0175 (5)	−0.0053 (5)
C4	0.0464 (9)	0.0480 (11)	0.0350 (8)	0	0.0148 (7)	0

Geometric parameters (Å, º)

Cu1—Cl1	2.2510 (5)	C11—H11F	0.96
Cu1—Cl2	2.2916 (5)	C2—C3	1.380 (2)
N1—C2	1.3641 (16)	C2—C21	1.492 (2)
N1—C11	1.472 (3)	C21—H21A	0.96
C11—H11A	0.96	C21—H21B	0.96
C11—H11B	0.96	C21—H21C	0.96
C11—H11C	0.96	C3—C4	1.3760 (19)
C11—H11D	0.96	C3—H3	0.93
C11—H11E	0.96	C4—H4	0.93
C2—N1—C2^i	121.69 (17)	N1—C2—C3	119.04 (13)
C2—N1—C11	119.15 (9)	N1—C2—C21	119.95 (15)
N1—C11—H11A	109.5	C3—C2—C21	121.01 (14)
N1—C11—H11B	109.5	C2—C21—H21A	109.5
H11A—C11—H11B	109.5	C2—C21—H21B	109.5
N1—C11—H11C	109.5	H21A—C21—H21B	109.5
H11A—C11—H11C	109.5	C2—C21—H21C	109.5
H11B—C11—H11C	109.5	H21A—C21—H21C	109.5
N1—C11—H11D	109.5	H21B—C21—H21C	109.5
N1—C11—H11E	109.5	C2—C3—C4	120.36 (14)
H11D—C11—H11E	109.5	C2—C3—H3	119.8
N1—C11—H11F	109.5	C4—C3—H3	119.8
H11D—C11—H11F	109.5	C3^i—C4—C3	119.5 (2)
H11E—C11—H11F	109.5	C3—C4—H4	120.3

Symmetry code: (i) x, −y+1, z.

(Cl350K) bis(1,2,6-trimethylpyridinium) tetrachloridocuprate(II)

Crystal data

2(C8H12N)·Cl4Cu	Z = 2
Mr = 449.74	F(000) = 462
Triclinic, P1	Dx = 1.465 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9236 (4) Å	Cell parameters from 4596 reflections
b = 9.1502 (4) Å	θ = 3.5–27.5°
c = 16.1341 (8) Å	µ = 1.60 mm^−1
α = 75.409 (2)°	T = 350 K
β = 86.964 (3)°	Irregular, yellow
γ = 64.493 (3)°	0.30 × 0.27 × 0.11 mm
V = 1019.63 (8) Å^3

Data collection

KappaCCD diffractometer	4665 independent reflections
Radiation source: Enraf Nonius FR590	3361 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.5°
CCD rotation images, thick slices scans	h = −10→9
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −11→11
Tmin = 0.607, Tmax = 0.708	l = −20→20
19702 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.223	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1178P)^2 + 1.47486P] where P = (Fo^2 + 2Fc^2)/3
4665 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 1.15 e Å^−3
0 restraints	Δρmin = −0.62 e Å^−3
0 constraints

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
Cu1	0.22382 (9)	0.00383 (7)	0.74640 (4)	0.0522 (2)
Cl1	0.0662 (2)	0.28216 (19)	0.72557 (11)	0.0794 (5)
Cl2	0.2857 (3)	−0.0672 (2)	0.88837 (9)	0.0827 (5)
Cl3	0.1757 (3)	−0.2213 (2)	0.74462 (9)	0.0759 (5)
Cl4	0.3755 (3)	0.00888 (19)	0.62486 (11)	0.0861 (6)
N11	0.2455 (7)	0.3496 (6)	0.0966 (3)	0.0646 (12)
C111	0.2436 (14)	0.3140 (11)	0.1915 (4)	0.100 (3)
H11A	0.3647	0.2307	0.2166	0.150*
H11B	0.1511	0.2733	0.2103	0.150*
H11C	0.2137	0.4147	0.2090	0.150*
C12	0.2549 (8)	0.4921 (8)	0.0531 (4)	0.0641 (14)
C121	0.2642 (13)	0.6124 (11)	0.1001 (6)	0.104 (3)
H12A	0.1515	0.6552	0.1295	0.156*
H12B	0.2768	0.7036	0.0597	0.156*
H12C	0.3702	0.5549	0.1411	0.156*
C13	0.2513 (9)	0.5277 (8)	−0.0347 (4)	0.0729 (16)
H13	0.2562	0.6265	−0.0653	0.087*
C14	0.2409 (9)	0.4227 (9)	−0.0777 (4)	0.0763 (17)
H14	0.2364	0.4493	−0.1374	0.092*
C15	0.2370 (10)	0.2772 (9)	−0.0323 (4)	0.0781 (17)
H15	0.2330	0.2021	−0.0608	0.094*
C16	0.2389 (9)	0.2412 (8)	0.0554 (5)	0.0753 (17)
C161	0.2404 (14)	0.0787 (10)	0.1067 (7)	0.117 (3)
H16A	0.3249	0.0352	0.1566	0.175*
H16B	0.2808	−0.0003	0.0721	0.175*
H16C	0.1165	0.0976	0.1240	0.175*
N21	0.2641 (7)	0.6836 (6)	0.4246 (3)	0.0652 (13)
C211	0.2098 (13)	0.8662 (9)	0.4081 (7)	0.112 (3)
H21A	0.2118	0.8939	0.4615	0.168*
H21B	0.0859	0.9282	0.3806	0.168*
H21C	0.2966	0.8943	0.3714	0.168*
C22	0.1950 (8)	0.6077 (8)	0.4922 (4)	0.0639 (14)
C221	0.0665 (11)	0.7081 (11)	0.5498 (5)	0.099 (2)
H22A	0.0264	0.6375	0.5925	0.149*
H22B	−0.0409	0.7991	0.5162	0.149*
H22C	0.1320	0.7519	0.5774	0.149*
C23	0.2462 (9)	0.4406 (8)	0.5076 (4)	0.0672 (14)
H23	0.2033	0.3870	0.5548	0.081*
C24	0.3593 (9)	0.3513 (7)	0.4546 (4)	0.0671 (14)
H24	0.3904	0.2378	0.4645	0.081*
C25	0.4271 (8)	0.4287 (8)	0.3868 (4)	0.0659 (14)
H25	0.5067	0.3667	0.3513	0.079*
C26	0.3792 (8)	0.5979 (8)	0.3703 (4)	0.0660 (14)
C261	0.4510 (14)	0.6825 (12)	0.2971 (5)	0.108 (3)
H26A	0.3479	0.7692	0.2592	0.162*
H26B	0.5308	0.6028	0.2668	0.162*
H26C	0.5213	0.7309	0.3177	0.162*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0614 (4)	0.0505 (4)	0.0470 (4)	−0.0253 (3)	0.0093 (3)	−0.0152 (3)
Cl1	0.0868 (11)	0.0545 (8)	0.0799 (10)	−0.0136 (7)	0.0163 (8)	−0.0219 (7)
Cl2	0.1290 (15)	0.0779 (10)	0.0519 (8)	−0.0529 (10)	−0.0044 (8)	−0.0173 (7)
Cl3	0.1200 (13)	0.0788 (10)	0.0573 (8)	−0.0661 (10)	0.0185 (8)	−0.0250 (7)
Cl4	0.1210 (14)	0.0566 (8)	0.0736 (10)	−0.0357 (9)	0.0502 (9)	−0.0188 (7)
N11	0.063 (3)	0.068 (3)	0.060 (3)	−0.026 (2)	0.009 (2)	−0.017 (2)
C111	0.151 (8)	0.118 (6)	0.049 (3)	−0.080 (6)	0.027 (4)	−0.015 (4)
C12	0.061 (3)	0.067 (3)	0.070 (4)	−0.029 (3)	0.015 (3)	−0.025 (3)
C121	0.123 (7)	0.118 (6)	0.112 (6)	−0.074 (6)	0.039 (5)	−0.063 (5)
C13	0.081 (4)	0.065 (4)	0.071 (4)	−0.033 (3)	0.018 (3)	−0.014 (3)
C14	0.079 (4)	0.081 (4)	0.065 (4)	−0.033 (4)	0.009 (3)	−0.017 (3)
C15	0.083 (4)	0.084 (4)	0.078 (4)	−0.038 (4)	0.019 (3)	−0.036 (4)
C16	0.073 (4)	0.061 (4)	0.088 (5)	−0.030 (3)	0.018 (3)	−0.016 (3)
C161	0.136 (8)	0.078 (5)	0.140 (8)	−0.058 (5)	0.039 (6)	−0.018 (5)
N21	0.068 (3)	0.050 (2)	0.072 (3)	−0.018 (2)	−0.019 (2)	−0.016 (2)
C211	0.113 (6)	0.052 (4)	0.155 (8)	−0.021 (4)	−0.027 (6)	−0.022 (4)
C22	0.062 (3)	0.067 (3)	0.060 (3)	−0.019 (3)	−0.007 (3)	−0.025 (3)
C221	0.085 (5)	0.115 (6)	0.099 (5)	−0.024 (4)	0.007 (4)	−0.065 (5)
C23	0.072 (4)	0.067 (4)	0.059 (3)	−0.029 (3)	0.000 (3)	−0.012 (3)
C24	0.070 (3)	0.055 (3)	0.072 (4)	−0.023 (3)	0.002 (3)	−0.016 (3)
C25	0.062 (3)	0.067 (4)	0.067 (3)	−0.020 (3)	0.003 (3)	−0.029 (3)
C26	0.065 (3)	0.071 (4)	0.063 (3)	−0.030 (3)	−0.012 (3)	−0.016 (3)
C261	0.140 (8)	0.123 (7)	0.075 (5)	−0.079 (6)	−0.004 (5)	−0.006 (5)

Geometric parameters (Å, º)

Cu1—Cl1	2.2433 (16)	C161—H16B	0.96
Cu1—Cl2	2.2369 (16)	C161—H16C	0.96
Cu1—Cl3	2.2578 (15)	N21—C26	1.365 (8)
Cu1—Cl4	2.2461 (15)	N21—C22	1.362 (8)
N11—C16	1.346 (8)	N21—C211	1.489 (8)
N11—C12	1.348 (7)	C211—H21A	0.96
N11—C111	1.483 (8)	C211—H21B	0.96
C111—H11A	0.96	C211—H21C	0.96
C111—H11B	0.96	C22—C23	1.359 (9)
C111—H11C	0.96	C22—C221	1.506 (9)
C12—C13	1.370 (9)	C221—H22A	0.96
C12—C121	1.513 (9)	C221—H22B	0.96
C121—H12A	0.96	C221—H22C	0.96
C121—H12B	0.96	C23—C24	1.356 (8)
C121—H12C	0.96	C23—H23	0.93
C13—C14	1.351 (9)	C24—C25	1.365 (9)
C13—H13	0.93	C24—H24	0.93
C14—C15	1.361 (9)	C25—C26	1.381 (8)
C14—H14	0.93	C25—H25	0.93
C15—C16	1.368 (10)	C26—C261	1.471 (10)
C15—H15	0.93	C261—H26A	0.96
C16—C161	1.503 (9)	C261—H26B	0.96
C161—H16A	0.96	C261—H26C	0.96
Cl1—Cu1—Cl2	99.02 (7)	H16A—C161—H16C	109.5
Cl1—Cu1—Cl3	140.46 (8)	H16B—C161—H16C	109.5
Cl1—Cu1—Cl4	96.66 (6)	C26—N21—C22	121.9 (5)
Cl2—Cu1—Cl3	95.36 (6)	C26—N21—C211	118.7 (6)
Cl2—Cu1—Cl4	139.43 (9)	C22—N21—C211	119.3 (6)
Cl3—Cu1—Cl4	95.84 (6)	N21—C211—H21A	109.5
C16—N11—C12	121.1 (5)	N21—C211—H21B	109.5
C16—N11—C111	120.5 (6)	H21A—C211—H21B	109.5
C12—N11—C111	118.5 (5)	N21—C211—H21C	109.5
N11—C111—H11A	109.5	H21A—C211—H21C	109.5
N11—C111—H11B	109.5	H21B—C211—H21C	109.5
H11A—C111—H11B	109.5	N21—C22—C23	119.1 (6)
N11—C111—H11C	109.5	N21—C22—C221	120.0 (6)
H11A—C111—H11C	109.5	C23—C22—C221	120.9 (7)
H11B—C111—H11C	109.5	C22—C221—H22A	109.5
N11—C12—C13	118.6 (6)	C22—C221—H22B	109.5
N11—C12—C121	120.7 (6)	H22A—C221—H22B	109.5
C13—C12—C121	120.7 (6)	C22—C221—H22C	109.5
C12—C121—H12A	109.5	H22A—C221—H22C	109.5
C12—C121—H12B	109.5	H22B—C221—H22C	109.5
H12A—C121—H12B	109.5	C22—C23—C24	120.7 (6)
C12—C121—H12C	109.5	C22—C23—H23	119.7
H12A—C121—H12C	109.5	C24—C23—H23	119.7
H12B—C121—H12C	109.5	C22—C23—H23	119.7
C12—C13—C14	121.5 (6)	C23—C24—C25	119.7 (6)
C12—C13—H13	119.3	C23—C24—H24	120.1
C14—C13—H13	119.3	C25—C24—H24	120.1
C13—C14—C15	118.8 (6)	C24—C25—C26	120.9 (6)
C13—C14—H14	120.6	C24—C25—H25	119.6
C15—C14—H14	120.6	C26—C25—H25	119.6
C14—C15—C16	120.1 (6)	N21—C26—C25	117.6 (6)
C14—C15—H15	120	N21—C26—C261	121.1 (7)
C16—C15—H15	120	C25—C26—C261	121.3 (7)
N11—C16—C15	119.9 (6)	C26—C261—H26A	109.5
N11—C16—C161	119.3 (7)	C26—C261—H26B	109.5
C15—C16—C161	120.7 (7)	H26A—C261—H26B	109.5
C16—C161—H16A	109.5	C26—C261—H26C	109.5
C16—C161—H16B	109.5	H26A—C261—H26C	109.5
H16A—C161—H16B	109.5	H26B—C261—H26C	109.5
C16—C161—H16C	109.5

(Br100K) bis(1,2,6-trimethylpyridinium) tetrabromidocuprate(II)

Crystal data

2(C8H12N)·Br4Cu	F(000) = 606
Mr = 627.55	Dx = 2.081 Mg m^−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
a = 13.0879 (12) Å	Cell parameters from 1207 reflections
b = 9.4953 (10) Å	θ = 2.9–27.5°
c = 8.7957 (9) Å	µ = 9.07 mm^−1
β = 113.631 (6)°	T = 100 K
V = 1001.41 (17) Å^3	Block, dark purple
Z = 2	0.25 × 0.17 × 0.13 mm

Data collection

KappaCCD diffractometer	1212 independent reflections
Radiation source: Enraf Nonius FR590	1013 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 5.0°
CCD rotation images, thick slices scans	h = −16→16
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.140, Tmax = 0.341	l = −11→11
8979 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.183	H-atom parameters constrained
S = 1.21	w = 1/[σ^2(Fo^2) + (0.1097P)^2 + 4.1327P] where P = (Fo^2 + 2Fc^2)/3
1212 reflections	(Δ/σ)max < 0.001
62 parameters	Δρmax = 1.81 e Å^−3
0 restraints	Δρmin = −1.24 e Å^−3

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	Occ. (<1)
Cu1	0.0000	0.0000	0.0000	0.0263 (4)
Br1	0.06296 (8)	0.0000	0.29540 (11)	0.0297 (4)
Br2	0.0000	0.25773 (10)	0.0000	0.0302 (4)
N1	0.1715 (7)	0.5000	0.7027 (12)	0.0314 (18)
C11	0.2080 (9)	0.5000	0.8868 (12)	0.034 (2)
H11A	0.2142	0.5953	0.9259	0.052*	0.25
H11B	0.2791	0.4542	0.9376	0.052*	0.25
H11C	0.1541	0.4505	0.9152	0.052*	0.25
H11D	0.2174	0.4047	0.9265	0.052*	0.25
H11E	0.1525	0.5458	0.9149	0.052*	0.25
H11F	0.2775	0.5495	0.9373	0.052*	0.25
C2	0.1577 (6)	0.3754 (7)	0.6217 (9)	0.0297 (15)
C21	0.1743 (6)	0.2393 (7)	0.7156 (9)	0.0313 (15)
H21A	0.2507	0.2318	0.7928	0.047*
H21B	0.1562	0.1618	0.6391	0.047*
H21C	0.1267	0.2373	0.7749	0.047*
C3	0.1260 (6)	0.3744 (7)	0.4529 (9)	0.0304 (15)
H3	0.1160	0.2894	0.3962	0.036*
C4	0.1091 (9)	0.5000	0.3679 (13)	0.031 (2)
H4	0.0863	0.5000	0.2532	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0285 (8)	0.0282 (8)	0.0247 (8)	0.000	0.0135 (7)	0.000
Br1	0.0364 (6)	0.0287 (5)	0.0254 (5)	0.000	0.0137 (4)	0.000
Br2	0.0386 (6)	0.0279 (5)	0.0257 (5)	0.000	0.0147 (4)	0.000
N1	0.024 (4)	0.035 (4)	0.036 (5)	0.000	0.013 (3)	0.000
C11	0.034 (5)	0.042 (6)	0.026 (5)	0.000	0.011 (4)	0.000
C2	0.026 (3)	0.031 (4)	0.035 (4)	0.000 (3)	0.015 (3)	0.002 (3)
C21	0.038 (4)	0.029 (3)	0.031 (4)	−0.002 (3)	0.018 (3)	0.003 (3)
C3	0.030 (3)	0.033 (4)	0.029 (3)	−0.005 (3)	0.013 (3)	−0.006 (3)
C4	0.033 (5)	0.032 (5)	0.031 (5)	0.000	0.015 (4)	0.000

Geometric parameters (Å, º)

Cu1—Br1	2.3903 (10)	C11—H11F	0.96
Cu1—Br2	2.4472 (10)	C2—C3	1.372 (11)
N1—C2	1.355 (8)	C2—C21	1.501 (9)
N1—C11	1.493 (14)	C21—H21A	0.96
C11—H11A	0.96	C21—H21B	0.96
C11—H11B	0.96	C21—H21C	0.96
C11—H11C	0.96	C3—C4	1.377 (9)
C11—H11D	0.96	C3—H3	0.93
C11—H11E	0.96	C4—H4	0.93
Br2^i—Cu1—Br1	90.00 (1)	H11A—C11—H11F	56.3
C2—N1—C2^ii	121.6 (9)	H11B—C11—H11F	56.3
C2—N1—C11	119.1 (5)	H11C—C11—H11F	141.1
N1—C11—H11A	109.5	H11D—C11—H11F	109.5
N1—C11—H11B	109.5	H11E—C11—H11F	109.5
H11A—C11—H11B	109.5	N1—C2—C3	119.5 (7)
N1—C11—H11C	109.5	N1—C2—C21	120.2 (7)
H11A—C11—H11C	109.5	C3—C2—C21	120.3 (6)
H11B—C11—H11C	109.5	C2—C21—H21A	109.5
N1—C11—H11D	109.5	C2—C21—H21B	109.5
H11A—C11—H11D	141.1	H21A—C21—H21B	109.5
H11B—C11—H11D	56.3	C2—C21—H21C	109.5
H11C—C11—H11D	56.3	H21A—C21—H21C	109.5
N1—C11—H11E	109.5	H21B—C21—H21C	109.5
H11A—C11—H11E	56.3	C2—C3—C4	119.7 (7)
H11B—C11—H11E	141.1	C2—C3—H3	120.2
H11C—C11—H11E	56.3	C4—C3—H3	120.2
H11D—C11—H11E	109.5	C3^ii—C4—C3	119.9 (10)
N1—C11—H11F	109.5	C3—C4—H4	120

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y, z.

(Br295K) bis(1,2,6-trimethylpyridinium) tetrabromidocuprate(II)

Crystal data

2(C8H12N)·Br4Cu	Z = 2
Mr = 627.55	F(000) = 606
Triclinic, P1	Dx = 1.914 Mg m^−3
a = 8.0517 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3247 (3) Å	Cell parameters from 4896 reflections
c = 16.4524 (5) Å	θ = 2.9–27.5°
α = 75.997 (2)°	µ = 8.34 mm^−1
β = 88.567 (2)°	T = 295 K
γ = 65.757 (2)°	Block, dark purple
V = 1088.97 (6) Å^3	0.18 × 0.13 × 0.09 mm

Data collection

KappaCCD diffractometer	4944 independent reflections
Radiation source: Enraf Nonius FR590	3455 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 5.0°
CCD rotation images, thick slices scans	h = −10→10
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −11→12
Tmin = 0.283, Tmax = 0.441	l = −21→21
19577 measured reflections

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)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0263P)^2 + 1.3223P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4944 reflections	Δρmax = 1.02 e Å^−3
215 parameters	Δρmin = −1.17 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0180 (7)

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
Cu1	0.23260 (7)	−0.00372 (6)	0.74777 (3)	0.04590 (15)
Br1	0.07127 (7)	0.28358 (6)	0.72708 (3)	0.06407 (17)
Br2	0.29786 (9)	−0.07481 (7)	0.89555 (3)	0.06827 (18)
Br3	0.18592 (8)	−0.24057 (6)	0.74565 (3)	0.06183 (16)
Br4	0.38368 (8)	0.00421 (6)	0.62053 (3)	0.06410 (17)
N11	0.2434 (5)	0.3495 (5)	0.1013 (2)	0.0565 (10)
C111	0.2490 (9)	0.3140 (8)	0.1946 (3)	0.0794 (17)
H11A	0.1784	0.4124	0.2110	0.119*
H11B	0.3733	0.2706	0.2177	0.119*
H11C	0.1989	0.2360	0.2154	0.119*
C12	0.2593 (7)	0.4860 (6)	0.0582 (3)	0.0576 (12)
C121	0.2854 (9)	0.5956 (8)	0.1049 (4)	0.0830 (18)
H12A	0.3838	0.5327	0.1481	0.125*
H12B	0.1751	0.6484	0.1299	0.125*
H12C	0.3142	0.6761	0.0665	0.125*
C13	0.2524 (7)	0.5203 (6)	−0.0275 (3)	0.0644 (13)
H13	0.2622	0.6144	−0.0576	0.077*
C14	0.2315 (7)	0.4186 (6)	−0.0698 (3)	0.0668 (14)
H14	0.2259	0.4434	−0.1282	0.080*
C15	0.2190 (8)	0.2809 (7)	−0.0254 (3)	0.0679 (14)
H15	0.2054	0.2109	−0.0538	0.081*
C16	0.2260 (7)	0.2438 (6)	0.0606 (4)	0.0646 (13)
C161	0.2174 (10)	0.0896 (8)	0.1099 (5)	0.099 (2)
H16A	0.1139	0.1152	0.1428	0.149*
H16B	0.3273	0.0248	0.1464	0.149*
H16C	0.2055	0.0300	0.0720	0.149*
C211	0.2032 (9)	0.8685 (7)	0.4065 (5)	0.091 (2)
H21A	0.2197	0.9115	0.3492	0.137*
H21B	0.2769	0.8887	0.4435	0.137*
H21C	0.0769	0.9204	0.4165	0.137*
N21	0.2588 (5)	0.6919 (4)	0.4223 (3)	0.0549 (10)
C22	0.1918 (7)	0.6173 (6)	0.4887 (3)	0.0565 (12)
C221	0.0659 (9)	0.7157 (9)	0.5422 (4)	0.090 (2)
H22A	−0.0401	0.7997	0.5079	0.134*
H22B	0.1276	0.7640	0.5682	0.134*
H22C	0.0293	0.6466	0.5848	0.134*
C23	0.2432 (7)	0.4534 (6)	0.5046 (3)	0.0601 (12)
H23	0.2008	0.4008	0.5501	0.072*
C24	0.3562 (7)	0.3666 (6)	0.4541 (3)	0.0582 (12)
H24	0.3889	0.2555	0.4646	0.070*
C25	0.4210 (7)	0.4422 (6)	0.3887 (3)	0.0585 (12)
H25	0.4992	0.3822	0.3548	0.070*
C26	0.3723 (7)	0.6065 (6)	0.3718 (3)	0.0555 (11)
C261	0.4412 (9)	0.6899 (8)	0.2994 (4)	0.0854 (18)
H26A	0.5003	0.7478	0.3188	0.128*
H26B	0.3407	0.7651	0.2591	0.128*
H26C	0.5271	0.6108	0.2736	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0537 (3)	0.0432 (3)	0.0414 (3)	−0.0197 (2)	0.0081 (2)	−0.0131 (2)
Br1	0.0676 (3)	0.0457 (3)	0.0650 (3)	−0.0081 (2)	0.0079 (2)	−0.0177 (2)
Br2	0.1038 (4)	0.0597 (3)	0.0438 (3)	−0.0342 (3)	0.0005 (3)	−0.0167 (2)
Br3	0.0925 (4)	0.0637 (3)	0.0489 (3)	−0.0484 (3)	0.0170 (2)	−0.0215 (2)
Br4	0.0887 (4)	0.0478 (3)	0.0536 (3)	−0.0274 (3)	0.0300 (3)	−0.0132 (2)
N11	0.056 (2)	0.058 (2)	0.049 (2)	−0.0188 (19)	0.0100 (18)	−0.0125 (19)
C111	0.089 (4)	0.093 (4)	0.048 (3)	−0.037 (3)	0.013 (3)	−0.007 (3)
C12	0.057 (3)	0.056 (3)	0.061 (3)	−0.024 (2)	0.015 (2)	−0.016 (2)
C121	0.104 (5)	0.095 (5)	0.079 (4)	−0.059 (4)	0.030 (4)	−0.045 (4)
C13	0.077 (3)	0.051 (3)	0.058 (3)	−0.022 (3)	0.013 (3)	−0.010 (2)
C14	0.080 (4)	0.062 (3)	0.053 (3)	−0.024 (3)	0.010 (3)	−0.016 (3)
C15	0.079 (4)	0.066 (3)	0.067 (3)	−0.030 (3)	0.013 (3)	−0.032 (3)
C16	0.063 (3)	0.052 (3)	0.076 (4)	−0.021 (2)	0.017 (3)	−0.018 (3)
C161	0.123 (6)	0.069 (4)	0.118 (6)	−0.054 (4)	0.040 (5)	−0.024 (4)
C211	0.100 (5)	0.046 (3)	0.123 (6)	−0.025 (3)	−0.011 (4)	−0.020 (3)
N21	0.059 (2)	0.039 (2)	0.061 (2)	−0.0144 (18)	−0.0157 (19)	−0.0113 (18)
C22	0.055 (3)	0.064 (3)	0.048 (3)	−0.017 (2)	−0.004 (2)	−0.023 (2)
C221	0.084 (4)	0.107 (5)	0.080 (4)	−0.022 (4)	0.007 (3)	−0.060 (4)
C23	0.064 (3)	0.058 (3)	0.051 (3)	−0.022 (2)	−0.002 (2)	−0.006 (2)
C24	0.065 (3)	0.041 (2)	0.060 (3)	−0.017 (2)	0.000 (2)	−0.007 (2)
C25	0.057 (3)	0.053 (3)	0.063 (3)	−0.015 (2)	0.005 (2)	−0.023 (2)
C26	0.059 (3)	0.059 (3)	0.052 (3)	−0.027 (2)	−0.003 (2)	−0.014 (2)
C261	0.107 (5)	0.096 (5)	0.070 (4)	−0.064 (4)	0.014 (3)	−0.013 (3)

Geometric parameters (Å, º)

Cu1—Br1	2.3881 (7)	C161—H16B	0.9600
Cu1—Br2	2.3717 (7)	C161—H16C	0.9600
Cu1—Br3	2.3958 (7)	N21—C26	1.358 (6)
Cu1—Br4	2.3957 (7)	N21—C22	1.370 (6)
N11—C16	1.370 (7)	N21—C211	1.475 (6)
N11—C12	1.353 (6)	C211—H21A	0.9600
N11—C111	1.488 (6)	C211—H21B	0.9600
C111—H11A	0.9600	C211—H21C	0.9600
C111—H11B	0.9600	C22—C23	1.366 (7)
C111—H11C	0.9600	C22—C221	1.492 (7)
C12—C13	1.366 (7)	C221—H22A	0.9600
C12—C121	1.498 (7)	C221—H22B	0.9600
C121—H12A	0.9600	C221—H22C	0.9600
C121—H12B	0.9600	C23—C24	1.362 (7)
C121—H12C	0.9600	C23—H23	0.9300
C13—C14	1.367 (7)	C24—C25	1.355 (7)
C13—H13	0.9300	C24—H24	0.9300
C14—C15	1.356 (7)	C25—C26	1.372 (7)
C14—H14	0.9300	C25—H25	0.9300
C15—C16	1.370 (7)	C26—C261	1.484 (7)
C15—H15	0.9300	C261—H26A	0.9600
C16—C161	1.499 (7)	C261—H26B	0.9600
C161—H16A	0.9600	C261—H26C	0.9600
Br1—Cu1—Br2	98.19 (3)	C16—C161—H16C	109.5
Br1—Cu1—Br3	141.67 (3)	H16A—C161—H16C	109.5
Br1—Cu1—Br4	96.79 (3)	H16B—C161—H16C	109.5
Br2—Cu1—Br3	95.14 (3)	C26—N21—C22	121.3 (4)
Br2—Cu1—Br4	140.58 (3)	C26—N21—C211	120.5 (5)
Br3—Cu1—Br4	95.25 (2)	C22—N21—C211	118.2 (5)
C16—N11—C12	121.1 (4)	N21—C211—H21A	109.5
C16—N11—C111	120.3 (4)	N21—C211—H21B	109.5
C12—N11—C111	118.6 (5)	H21A—C211—H21B	109.5
N11—C111—H11A	109.5	N21—C211—H21C	109.5
N11—C111—H11B	109.5	H21A—C211—H21C	109.5
H11A—C111—H11B	109.5	H21B—C211—H21C	109.5
N11—C111—H11C	109.5	N21—C22—C23	118.9 (4)
H11A—C111—H11C	109.5	N21—C22—C221	119.6 (5)
H11B—C111—H11C	109.5	C23—C22—C221	121.5 (5)
N11—C12—C13	119.0 (5)	C22—C221—H22A	109.5
N11—C12—C121	119.8 (5)	C22—C221—H22B	109.5
C13—C12—C121	121.2 (5)	H22A—C221—H22B	109.5
C12—C121—H12A	109.5	C22—C221—H22C	109.5
C12—C121—H12B	109.5	H22A—C221—H22C	109.5
H12A—C121—H12B	109.5	H22B—C221—H22C	109.5
C12—C121—H12C	109.5	C22—C23—C24	120.4 (5)
H12A—C121—H12C	109.5	C22—C23—H23	119.8
H12B—C121—H12C	109.5	C24—C23—H23	119.8
C12—C13—C14	121.0 (5)	C23—C24—H24	120.0
C12—C13—H13	119.5	C23—C24—C25	120.0 (5)
C14—C13—H13	119.5	C25—C24—H24	120.0
C13—C14—C15	119.2 (5)	C24—C25—C26	120.7 (5)
C13—C14—H14	120.4	C24—C25—H25	119.6
C15—C14—H14	120.4	C26—C25—H25	119.6
C14—C15—C16	120.8 (5)	C25—C26—N21	118.8 (4)
C14—C15—H15	119.6	C25—C26—C261	120.8 (5)
C16—C15—H15	119.6	N21—C26—C261	120.5 (5)
C15—C16—N11	118.9 (5)	C26—C261—H26A	109.5
C15—C16—C161	121.0 (6)	C26—C261—H26B	109.5
N11—C16—C161	120.2 (5)	H26A—C261—H26B	109.5
C16—C161—H16A	109.5	C26—C261—H26C	109.5
C16—C161—H16B	109.5	H26A—C261—H26C	109.5
H16A—C161—H16B	109.5	H26B—C261—H26C	109.5

(26lutcl100k) bis(2,6-dimethylpyridinium) tetrachlorocuprate(II)

Crystal data

2(C7H10N)·Cl4Cu	F(000) = 860
Mr = 421.69	Dx = 1.566 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.3451 (3) Å	Cell parameters from 4572 reflections
b = 7.5569 (2) Å	θ = 2.9–36.3°
c = 16.6038 (3) Å	µ = 1.81 mm^−1
β = 96.309 (1)°	T = 100 K
V = 1789.03 (7) Å^3	Prism, yellow
Z = 4	0.34 × 0.17 × 0.13 mm

Data collection

KappaCCD diffractometer	4334 independent reflections
Radiation source: Enraf Nonius FR590	3401 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 9 pixels mm^-1	θmax = 36.3°, θmin = 3.8°
CCD rotation images, thick slices scans	h = −23→23
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.677, Tmax = 0.795	l = −27→27
30011 measured reflections

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)] = 0.033	All H-atom parameters refined
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0296P)^2 + 2.1947P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4334 reflections	Δρmax = 0.53 e Å^−3
137 parameters	Δρmin = −0.71 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (3)

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
Cu1	0.5000	0.78691 (3)	0.7500	0.01429 (6)
Cl1	0.64461 (2)	0.67683 (5)	0.792735 (19)	0.01941 (7)
Cl2	0.53611 (2)	0.87687 (5)	0.628816 (19)	0.02024 (8)
N1	0.70853 (8)	0.54299 (15)	0.62716 (7)	0.01482 (19)
H1	0.6910 (12)	0.568 (2)	0.6738 (11)	0.014 (4)*
C2	0.79524 (9)	0.59802 (18)	0.61463 (8)	0.0156 (2)
C21	0.85264 (10)	0.6858 (2)	0.68376 (9)	0.0213 (3)
H21A	0.839 (2)	0.805 (4)	0.6897 (17)	0.062 (8)*
H21B	0.8464 (17)	0.628 (3)	0.7312 (15)	0.040 (6)*
H21C	0.9142 (19)	0.677 (3)	0.6778 (15)	0.047 (7)*
C3	0.82433 (9)	0.57174 (19)	0.53882 (8)	0.0177 (2)
H3	0.8868 (14)	0.608 (3)	0.5291 (11)	0.019 (5)*
C4	0.76444 (10)	0.49097 (19)	0.47862 (8)	0.0187 (2)
H4	0.7848 (13)	0.472 (3)	0.4266 (11)	0.020 (5)*
C5	0.67645 (10)	0.43193 (19)	0.49512 (8)	0.0179 (2)
H5	0.6349 (14)	0.374 (3)	0.4548 (12)	0.019 (5)*
C6	0.64907 (9)	0.45752 (18)	0.57128 (8)	0.0156 (2)
C61	0.55873 (10)	0.3916 (2)	0.59706 (10)	0.0217 (3)
H61A	0.5188 (17)	0.351 (3)	0.5489 (14)	0.039 (6)*
H61B	0.5280 (17)	0.475 (4)	0.6231 (15)	0.044 (7)*
H61C	0.5681 (19)	0.297 (4)	0.6306 (16)	0.051 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01556 (10)	0.01682 (11)	0.01117 (10)	0.000	0.00451 (7)	0.000
Cl1	0.02007 (14)	0.02513 (17)	0.01322 (13)	0.00581 (12)	0.00270 (10)	0.00067 (11)
Cl2	0.02107 (14)	0.02548 (17)	0.01538 (14)	0.00395 (12)	0.00744 (10)	0.00633 (11)
N1	0.0156 (4)	0.0160 (5)	0.0133 (4)	0.0008 (4)	0.0033 (3)	−0.0004 (4)
C2	0.0155 (5)	0.0146 (5)	0.0166 (5)	0.0014 (4)	0.0021 (4)	0.0008 (4)
C21	0.0183 (6)	0.0235 (7)	0.0217 (6)	−0.0027 (5)	0.0011 (5)	−0.0039 (5)
C3	0.0173 (5)	0.0186 (6)	0.0178 (6)	0.0022 (5)	0.0048 (4)	0.0019 (5)
C4	0.0225 (6)	0.0201 (6)	0.0141 (5)	0.0039 (5)	0.0051 (4)	0.0002 (4)
C5	0.0198 (6)	0.0180 (6)	0.0156 (5)	0.0027 (5)	0.0001 (4)	−0.0016 (4)
C6	0.0150 (5)	0.0155 (6)	0.0164 (5)	0.0010 (4)	0.0016 (4)	0.0002 (4)
C61	0.0180 (6)	0.0245 (7)	0.0228 (7)	−0.0033 (5)	0.0031 (5)	0.0003 (5)

Geometric parameters (Å, º)

Cu1—Cl1	2.2749 (3)	C3—C4	1.386 (2)
Cu1—Cl2	2.2379 (3)	C3—H3	0.967 (19)
N1—C6	1.3534 (17)	C4—C5	1.394 (2)
N1—C2	1.3491 (17)	C4—H4	0.953 (19)
N1—H1	0.862 (18)	C5—C6	1.3784 (19)
C2—C3	1.3833 (18)	C5—H5	0.951 (19)
C2—C21	1.493 (2)	C6—C61	1.4942 (19)
C21—H21A	0.93 (3)	C61—H61A	0.98 (2)
C21—H21B	0.91 (2)	C61—H61B	0.91 (3)
C21—H21C	0.90 (3)	C61—H61C	0.91 (3)
Cl1—Cu1—Cl1^i	137.10 (2)	C2—C3—H3	119.3 (11)
Cl1—Cu1—Cl2	95.640 (12)	C4—C3—H3	121.0 (11)
Cl1—Cu1—Cl2^i	97.116 (12)	C3—C4—C5	120.15 (12)
Cl2—Cu1—Cl2^i	144.63 (2)	C3—C4—H4	119.5 (12)
C6—N1—C2	124.31 (11)	C5—C4—H4	120.3 (12)
C6—N1—H1	119.8 (12)	C4—C5—C6	119.39 (13)
C2—N1—H1	115.9 (12)	C4—C5—H5	121.3 (12)
N1—C2—C3	118.14 (12)	C6—C5—H5	119.3 (12)
N1—C2—C21	117.28 (12)	C5—C6—N1	118.31 (12)
C3—C2—C21	124.57 (12)	C5—C6—C61	124.03 (13)
C2—C21—H21A	114.0 (18)	N1—C6—C61	117.63 (12)
C2—C21—H21B	110.6 (15)	C6—C61—H61A	108.6 (14)
H21A—C21—H21B	109 (2)	C6—C61—H61B	112.7 (16)
C2—C21—H21C	110.3 (16)	H61A—C61—H61B	110 (2)
H21A—C21—H21C	108 (2)	C6—C61—H61C	111.3 (17)
H21B—C21—H21C	104 (2)	H61A—C61—H61C	107 (2)
C2—C3—C4	119.62 (12)	H61B—C61—H61C	108 (2)

Symmetry code: (i) −x+1, y, −z+3/2.

(26lutclrt) bis(2,6-dimethylpyridinium)tetrachloridocuprate(II)

Crystal data

2(C7H10N)·Cl4Cu	F(000) = 860
Mr = 421.66	Dx = 1.512 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
a = 14.4831 (3) Å	Cell parameters from 3125 reflections
b = 7.7267 (2) Å	θ = 2.9–31.0°
c = 16.6432 (3) Å	µ = 1.75 mm^−1
β = 95.840 (1)°	T = 295 K
V = 1852.82 (7) Å^3	Irregular, yellow
Z = 4	0.33 × 0.28 × 0.17 mm

Data collection

KappaCCD diffractometer	2939 independent reflections
Radiation source: Enraf Nonius FR590	2250 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 9 pixels mm^-1	θmax = 31.0°, θmin = 4.6°
CCD rotation images, thick slices scans	h = −20→20
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −10→11
Tmin = 0.578, Tmax = 0.653	l = −24→24
26631 measured reflections

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)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0429P)^2 + 1.1046P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2939 reflections	Δρmax = 0.55 e Å^−3
97 parameters	Δρmin = −0.40 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0246 (12)

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	Occ. (<1)
Cu1	0.5000	0.78550 (4)	0.7500	0.04263 (13)
Cl1	0.64137 (4)	0.67281 (8)	0.79331 (3)	0.06004 (17)
Cl2	0.53700 (4)	0.87649 (8)	0.63014 (3)	0.06239 (18)
N1	0.70831 (10)	0.5432 (2)	0.62804 (9)	0.0418 (3)
H1	0.6896	0.5633	0.6746	0.050*
C2	0.79312 (13)	0.5994 (2)	0.61480 (11)	0.0445 (4)
C21	0.84952 (17)	0.6870 (3)	0.68284 (16)	0.0633 (6)
H21A	0.8150	0.6910	0.7291	0.095*	0.50
H21B	0.8639	0.8027	0.6671	0.095*	0.50
H21C	0.9061	0.6238	0.6962	0.095*	0.50
H21D	0.9083	0.7206	0.6659	0.095*	0.50
H21E	0.8594	0.6089	0.7278	0.095*	0.50
H21F	0.8172	0.7878	0.6987	0.095*	0.50
C3	0.82219 (14)	0.5718 (3)	0.53938 (13)	0.0512 (5)
H3	0.8807	0.6083	0.5283	0.061*
C4	0.76432 (16)	0.4902 (3)	0.48086 (12)	0.0546 (5)
H4	0.7831	0.4746	0.4295	0.066*
C5	0.67803 (15)	0.4310 (3)	0.49782 (12)	0.0511 (5)
H5	0.6393	0.3741	0.4583	0.061*
C6	0.65021 (13)	0.4571 (2)	0.57318 (11)	0.0435 (4)
C61	0.56038 (16)	0.3936 (3)	0.59925 (15)	0.0630 (6)
H61A	0.5560	0.4269	0.6543	0.094*	0.50
H61B	0.5578	0.2698	0.5949	0.094*	0.50
H61C	0.5097	0.4434	0.5653	0.094*	0.50
H61D	0.5263	0.3331	0.5554	0.094*	0.50
H61E	0.5245	0.4903	0.6148	0.094*	0.50
H61F	0.5726	0.3166	0.6444	0.094*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0478 (2)	0.0486 (2)	0.03362 (17)	0.000	0.01455 (12)	0.000
Cl1	0.0623 (3)	0.0808 (4)	0.0377 (2)	0.0206 (3)	0.0083 (2)	0.0031 (2)
Cl2	0.0650 (3)	0.0784 (4)	0.0477 (3)	0.0128 (3)	0.0251 (2)	0.0229 (2)
N1	0.0432 (8)	0.0455 (8)	0.0375 (7)	0.0029 (6)	0.0090 (6)	0.0003 (6)
C2	0.0432 (9)	0.0423 (9)	0.0485 (10)	0.0034 (7)	0.0075 (7)	0.0014 (7)
C21	0.0528 (12)	0.0680 (14)	0.0691 (14)	−0.0092 (10)	0.0056 (10)	−0.0125 (11)
C3	0.0474 (10)	0.0531 (11)	0.0557 (11)	0.0057 (8)	0.0180 (8)	0.0069 (9)
C4	0.0660 (13)	0.0587 (12)	0.0414 (9)	0.0153 (10)	0.0174 (8)	0.0032 (8)
C5	0.0594 (12)	0.0512 (11)	0.0420 (9)	0.0101 (9)	0.0018 (8)	−0.0037 (8)
C6	0.0441 (9)	0.0427 (9)	0.0437 (9)	0.0037 (7)	0.0039 (7)	0.0006 (7)
C61	0.0497 (11)	0.0725 (15)	0.0670 (14)	−0.0105 (11)	0.0075 (10)	−0.0023 (11)

Geometric parameters (Å, º)

Cu1—Cl1	2.2736 (5)	C3—C4	1.372 (3)
Cu1—Cl2	2.2312 (6)	C3—H3	0.9300
N1—C6	1.352 (2)	C4—C5	1.387 (3)
N1—C2	1.342 (2)	C4—H4	0.9300
N1—H1	0.8600	C5—C6	1.371 (3)
C2—C3	1.381 (3)	C5—H5	0.9300
C2—C21	1.490 (3)	C6—C61	1.495 (3)
C21—H21A	0.9600	C61—H61A	0.9600
C21—H21B	0.9600	C61—H61B	0.9600
C21—H21C	0.9600	C61—H61C	0.9600
C21—H21D	0.9600	C61—H61D	0.9600
C21—H21E	0.9600	C61—H61E	0.9600
C21—H21F	0.9600	C61—H61F	0.9600
Cl1—Cu1—Cl1^i	134.96 (4)	C2—C3—H3	120.1
Cl1—Cu1—Cl2	96.52 (2)	C4—C3—H3	120.1
Cl1—Cu1—Cl2^i	97.34 (2)	C3—C4—C5	120.35 (18)
Cl2—Cu1—Cl2^i	143.27 (4)	C3—C4—H4	119.8
C6—N1—C2	124.43 (16)	C5—C4—H4	119.8
C6—N1—H1	117.8	C4—C5—C6	119.53 (19)
C2—N1—H1	117.8	C4—C5—H5	120.2
N1—C2—C3	117.93 (18)	C6—C5—H5	120.2
N1—C2—C21	117.54 (18)	C5—C6—N1	118.00 (18)
C3—C2—C21	124.53 (19)	C5—C6—C61	124.25 (19)
C2—C21—H21A	109.5	N1—C6—C61	117.73 (18)
C2—C21—H21B	109.5	C6—C61—H61A	109.5
H21A—C21—H21B	109.5	C6—C61—H61B	109.5
C2—C21—H21C	109.5	H61A—C61—H61B	109.5
H21A—C21—H21C	109.5	C6—C61—H61C	109.5
H21B—C21—H21C	109.5	H61A—C61—H61C	109.5
C2—C21—H21D	109.5	H61B—C61—H61C	109.5
C2—C21—H21E	109.5	C6—C61—H61D	109.5
H21D—C21—H21E	109.5	C6—C61—H61E	109.5
C2—C21—H21F	109.5	H61D—C61—H61E	109.5
H21D—C21—H21F	109.5	C6—C61—H61F	109.5
H21E—C21—H21F	109.5	H61D—C61—H61F	109.5
C2—C3—C4	119.71 (19)	H61E—C61—H61F	109.5

Symmetry code: (i) −x+1, y, −z+3/2.

(26lutbr100k) bis(2,6-dimethylpyridinium) tetrabromidocuprate(II)

Crystal data

2(C7H10N)·Br4Cu	F(000) = 1148
Mr = 599.5	Dx = 2.068 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3568 reflections
a = 14.5510 (3) Å	θ = 2.9–32.0°
b = 7.8249 (2) Å	µ = 9.43 mm^−1
c = 17.0624 (3) Å	T = 100 K
β = 97.540 (1)°	Prism, dark purple
V = 1925.93 (7) Å^3	0.34 × 0.23 × 0.05 mm
Z = 4

Data collection

KappaCCD diffractometer	3356 independent reflections
Radiation source: Enraf Nonius FR590	2453 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 9 pixels mm^-1	θmax = 32.1°, θmin = 3.9°
CCD rotation images, thick slices scans	h = −21→21
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −11→11
Tmin = 0.094, Tmax = 0.159	l = −25→25
40655 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 6.079P] where P = (Fo^2 + 2Fc^2)/3
3356 reflections	(Δ/σ)max = 0.001
96 parameters	Δρmax = 0.80 e Å^−3
0 restraints	Δρmin = −1.14 e Å^−3
0 constraints

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	Occ. (<1)
Cu1	0.5	0.81548 (8)	0.75	0.01725 (14)
Br1	0.64826 (3)	0.69894 (5)	0.802284 (19)	0.02023 (10)
Br2	0.54469 (3)	0.91164 (5)	0.62839 (2)	0.02324 (11)
N1	0.7063 (2)	0.5633 (4)	0.63017 (17)	0.0178 (6)
H1	0.6889	0.5904	0.6748	0.021*
C2	0.7902 (2)	0.6155 (4)	0.6161 (2)	0.0169 (7)
C21	0.8476 (3)	0.7115 (5)	0.6798 (2)	0.0264 (8)
H21A	0.814	0.724	0.7242	0.04*	0.5
H21B	0.8619	0.8224	0.6605	0.04*	0.5
H21C	0.9041	0.6502	0.6957	0.04*	0.5
H21D	0.906	0.7404	0.6627	0.04*	0.5
H21E	0.8582	0.642	0.7265	0.04*	0.5
H21F	0.8159	0.8142	0.6913	0.04*	0.5
C3	0.8178 (3)	0.5756 (5)	0.5439 (2)	0.0204 (7)
H3	0.8759	0.609	0.5324	0.025*
C4	0.7584 (3)	0.4855 (5)	0.4886 (2)	0.0220 (7)
H4	0.7758	0.4618	0.4393	0.026*
C5	0.6727 (3)	0.4304 (5)	0.5067 (2)	0.0218 (8)
H5	0.6335	0.367	0.4703	0.026*
C6	0.6466 (3)	0.4707 (5)	0.5791 (2)	0.0193 (7)
C61	0.5571 (3)	0.4142 (5)	0.6057 (2)	0.0248 (8)
H61A	0.5535	0.4571	0.6579	0.037*	0.5
H61B	0.5546	0.2916	0.6062	0.037*	0.5
H61C	0.5061	0.4577	0.5699	0.037*	0.5
H61D	0.5226	0.3472	0.5648	0.037*	0.5
H61E	0.5215	0.5126	0.6165	0.037*	0.5
H61F	0.5701	0.3466	0.6528	0.037*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0188 (3)	0.0197 (3)	0.0142 (3)	0	0.0057 (2)	0
Br1	0.02187 (18)	0.02394 (19)	0.01505 (16)	0.00360 (14)	0.00304 (12)	0.00055 (14)
Br2	0.02448 (19)	0.0279 (2)	0.01908 (17)	0.00444 (16)	0.00933 (13)	0.00703 (15)
N1	0.0188 (14)	0.0212 (15)	0.0146 (13)	0.0018 (12)	0.0061 (11)	0.0016 (11)
C2	0.0196 (17)	0.0118 (15)	0.0197 (16)	0.0015 (13)	0.0041 (13)	0.0034 (13)
C21	0.0248 (19)	0.027 (2)	0.0271 (19)	−0.0069 (16)	0.0029 (15)	−0.0079 (16)
C3	0.0206 (17)	0.0197 (17)	0.0218 (17)	0.0027 (15)	0.0061 (14)	0.0042 (14)
C4	0.0232 (18)	0.0253 (19)	0.0181 (16)	0.0083 (16)	0.0054 (14)	0.0010 (15)
C5	0.0240 (18)	0.0235 (19)	0.0170 (16)	0.0029 (15)	−0.0009 (13)	−0.0026 (14)
C6	0.0187 (17)	0.0176 (16)	0.0212 (16)	0.0012 (14)	0.0010 (13)	0.0013 (14)
C61	0.0212 (18)	0.028 (2)	0.0262 (18)	−0.0025 (16)	0.0063 (14)	0.0007 (16)

Geometric parameters (Å, º)

Cu1—Br1	2.4034 (4)	C3—C4	1.385 (5)
Cu1—Br2	2.3768 (4)	C3—H3	0.93
N1—C6	1.356 (5)	C4—C5	1.392 (5)
N1—C2	1.339 (5)	C4—H4	0.93
N1—H1	0.86	C5—C6	1.376 (5)
C2—C3	1.382 (5)	C5—H5	0.93
C2—C21	1.484 (5)	C6—C61	1.500 (5)
C21—H21A	0.96	C61—H61A	0.96
C21—H21B	0.96	C61—H61B	0.96
C21—H21C	0.96	C61—H61C	0.96
C21—H21D	0.96	C61—H61D	0.96
C21—H21E	0.96	C61—H61E	0.96
C21—H21F	0.96	C61—H61F	0.96
Br1—Cu1—Br1^i	135.40 (3)	C2—C3—H3	120.2
Br1—Cu1—Br2	96.261 (12)	C4—C3—H3	120.2
Br1—Cu1—Br2^i	97.538 (13)	C3—C4—C5	120.3 (3)
Br2—Cu1—Br2^i	143.09 (4)	C3—C4—H4	119.9
C6—N1—C2	124.8 (3)	C5—C4—H4	119.9
C6—N1—H1	117.6	C4—C5—C6	119.3 (3)
C2—N1—H1	117.6	C4—C5—H5	120.4
N1—C2—C3	118.0 (3)	C6—C5—H5	120.4
N1—C2—C21	117.6 (3)	C5—C6—N1	118.0 (3)
C3—C2—C21	124.4 (3)	C5—C6—C61	123.8 (3)
C2—C21—H21A	109.5	N1—C6—C61	118.1 (3)
C2—C21—H21B	109.5	C6—C61—H61A	109.5
H21A—C21—H21B	109.5	C6—C61—H61B	109.5
C2—C21—H21C	109.5	H61A—C61—H61B	109.5
H21A—C21—H21C	109.5	C6—C61—H61C	109.5
H21B—C21—H21C	109.5	H61A—C61—H61C	109.5
C2—C21—H21D	109.5	H61B—C61—H61C	109.5
C2—C21—H21E	109.5	C6—C61—H61D	109.5
H21D—C21—H21E	109.5	C6—C61—H61E	109.5
C2—C21—H21F	109.5	H61D—C61—H61E	109.5
H21D—C21—H21F	109.5	C6—C61—H61F	109.5
H21E—C21—H21F	109.5	H61D—C61—H61F	109.5
C2—C3—C4	119.6 (3)	H61E—C61—H61F	109.5

Symmetry code: (i) −x+1, y, −z+3/2.

(26lutbrrt) bis(2,6-dimethylpyridinium) tetrabromidocuprate(II)

Crystal data

2(C7H10N)·Br4Cu	F(000) = 1148
Mr = 599.5	Dx = 2.001 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.6041 (3) Å	Cell parameters from 2720 reflections
b = 7.9883 (2) Å	θ = 2.9–28.7°
c = 17.1986 (3) Å	µ = 9.13 mm^−1
β = 97.345 (1)°	T = 295 K
V = 1989.96 (7) Å^3	Prism, dark purple
Z = 4	0.25 × 0.21 × 0.13 mm

Data collection

KappaCCD diffractometer	2558 independent reflections
Radiation source: Enraf Nonius FR590	2034 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 9 pixels mm^-1	θmax = 28.7°, θmin = 4.8°
CCD rotation images, thick slices scans	h = −19→19
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −9→10
Tmin = 0.115, Tmax = 0.176	l = −23→22
26583 measured reflections

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)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.0299P)^2 + 3.2871P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
2558 reflections	Δρmax = 0.73 e Å^−3
98 parameters	Δρmin = −0.78 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (2)

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	Occ. (<1)
Cu1	0.5000	0.80484 (7)	0.7500	0.04252 (14)
Br1	0.64681 (2)	0.68803 (5)	0.801568 (17)	0.05525 (13)
Br2	0.54416 (2)	0.90076 (5)	0.629655 (19)	0.06362 (14)
N1	0.70734 (16)	0.5567 (3)	0.63033 (13)	0.0424 (5)
H1	0.6901	0.5817	0.6749	0.036 (7)*
C2	0.7903 (2)	0.6114 (4)	0.61582 (18)	0.0450 (6)
C21	0.8472 (3)	0.7059 (5)	0.6789 (2)	0.0665 (10)
H21A	0.8142	0.7154	0.7235	0.100*	0.50
H21B	0.8598	0.8157	0.6602	0.100*	0.50
H21C	0.9043	0.6478	0.6938	0.100*	0.50
H21D	0.9047	0.7372	0.6615	0.100*	0.50
H21E	0.8590	0.6369	0.7248	0.100*	0.50
H21F	0.8146	0.8048	0.6912	0.100*	0.50
C3	0.8166 (2)	0.5746 (4)	0.54375 (19)	0.0532 (8)
H3	0.8737	0.6103	0.5316	0.064*
C4	0.7589 (2)	0.4856 (5)	0.48976 (18)	0.0556 (8)
H4	0.7763	0.4636	0.4406	0.067*
C5	0.6752 (2)	0.4286 (4)	0.50786 (18)	0.0539 (8)
H5	0.6368	0.3659	0.4716	0.065*
C6	0.6487 (2)	0.4650 (4)	0.57986 (17)	0.0450 (6)
C61	0.5607 (2)	0.4083 (5)	0.6070 (2)	0.0656 (9)
H61A	0.5574	0.4497	0.6590	0.098*	0.50
H61B	0.5587	0.2882	0.6073	0.098*	0.50
H61C	0.5093	0.4506	0.5721	0.098*	0.50
H61D	0.5262	0.3426	0.5666	0.098*	0.50
H61E	0.5249	0.5041	0.6183	0.098*	0.50
H61F	0.5743	0.3418	0.6535	0.098*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0480 (3)	0.0479 (3)	0.0342 (2)	0.000	0.01496 (19)	0.000
Br1	0.0595 (2)	0.0693 (2)	0.03708 (17)	0.01365 (16)	0.00671 (13)	0.00147 (13)
Br2	0.0676 (2)	0.0771 (3)	0.0518 (2)	0.01493 (18)	0.02882 (15)	0.02479 (17)
N1	0.0468 (13)	0.0432 (13)	0.0391 (12)	0.0044 (10)	0.0122 (10)	0.0000 (10)
C2	0.0454 (15)	0.0411 (15)	0.0493 (15)	0.0049 (13)	0.0099 (12)	0.0025 (13)
C21	0.058 (2)	0.068 (2)	0.074 (2)	−0.0123 (18)	0.0111 (17)	−0.0123 (19)
C3	0.0510 (17)	0.0586 (19)	0.0534 (17)	0.0065 (15)	0.0192 (14)	0.0075 (15)
C4	0.0627 (19)	0.065 (2)	0.0405 (15)	0.0131 (17)	0.0138 (14)	0.0009 (15)
C5	0.0603 (19)	0.0563 (19)	0.0433 (16)	0.0083 (16)	0.0004 (13)	−0.0054 (14)
C6	0.0458 (15)	0.0446 (16)	0.0447 (14)	0.0038 (13)	0.0058 (12)	−0.0002 (13)
C61	0.0537 (19)	0.072 (2)	0.072 (2)	−0.0116 (18)	0.0096 (16)	−0.0014 (19)

Geometric parameters (Å, º)

Cu1—Br1	2.4016 (4)	C3—C4	1.371 (5)
Cu1—Br2	2.3724 (3)	C3—H3	0.9300
N1—C6	1.354 (4)	C4—C5	1.377 (5)
N1—C2	1.342 (4)	C4—H4	0.9300
N1—H1	0.8600	C5—C6	1.375 (4)
C2—C3	1.375 (4)	C5—H5	0.9300
C2—C21	1.486 (5)	C6—C61	1.493 (5)
C21—H21A	0.9600	C61—H61A	0.9600
C21—H21B	0.9600	C61—H61B	0.9600
C21—H21C	0.9600	C61—H61C	0.9600
C21—H21D	0.9600	C61—H61D	0.9600
C21—H21E	0.9600	C61—H61E	0.9600
C21—H21F	0.9600	C61—H61F	0.9600
Br1—Cu1—Br1^i	134.28 (3)	C2—C3—H3	119.9
Br1—Cu1—Br2	96.790 (11)	C4—C3—H3	119.9
Br1—Cu1—Br2^i	97.627 (12)	C3—C4—C5	120.4 (3)
Br2—Cu1—Br2^i	142.32 (3)	C3—C4—H4	119.8
C6—N1—C2	124.7 (3)	C5—C4—H4	119.8
C6—N1—H1	117.7	C4—C5—C6	119.6 (3)
C2—N1—H1	117.7	C4—C5—H5	120.2
N1—C2—C3	117.5 (3)	C6—C5—H5	120.2
N1—C2—C21	117.6 (3)	C5—C6—N1	117.7 (3)
C3—C2—C21	124.9 (3)	C5—C6—C61	124.7 (3)
C2—C21—H21A	109.5	N1—C6—C61	117.6 (3)
C2—C21—H21B	109.5	C6—C61—H61A	109.5
H21A—C21—H21B	109.5	C6—C61—H61B	109.5
C2—C21—H21C	109.5	H61A—C61—H61B	109.5
H21A—C21—H21C	109.5	C6—C61—H61C	109.5
H21B—C21—H21C	109.5	H61A—C61—H61C	109.5
C2—C21—H21D	109.5	H61B—C61—H61C	109.5
C2—C21—H21E	109.5	C6—C61—H61D	109.5
H21D—C21—H21E	109.5	C6—C61—H61E	109.5
C2—C21—H21F	109.5	H61D—C61—H61E	109.5
H21D—C21—H21F	109.5	C6—C61—H61F	109.5
H21E—C21—H21F	109.5	H61D—C61—H61F	109.5
C2—C3—C4	120.2 (3)	H61E—C61—H61F	109.5

Symmetry code: (i) −x+1, y, −z+3/2.

(26lut100kortho) bis(2,6-dimethylpyridinium) tetrachloridocuprate(II)

Crystal data

2(C7H10N)·Cl4Cu	Dx = 1.509 Mg m^−3
Mr = 421.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 3360 reflections
a = 16.9587 (3) Å	θ = 2.9–31.0°
b = 7.8858 (1) Å	µ = 1.75 mm^−1
c = 13.8774 (3) Å	T = 100 K
V = 1855.86 (6) Å^3	Irregular, yellow
Z = 4	0.33 × 0.25 × 0.13 mm
F(000) = 860

Data collection

KappaCCD diffractometer	2952 independent reflections
Graphite monochromator	2386 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.019
CCD scans	θmax = 31.0°, θmin = 4.4°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −24→24
Tmin = 0.629, Tmax = 0.663	k = −11→11
59438 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 0.970P] where P = (Fo^2 + 2Fc^2)/3
2952 reflections	(Δ/σ)max = 0.001
120 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.63 e Å^−3

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
Cu1	0.5000	0.19627 (4)	0.7500	0.01663 (8)
Cl1	0.45461 (2)	0.32504 (6)	0.61533 (3)	0.02629 (11)
Cl2	0.61240 (2)	0.08444 (5)	0.69371 (3)	0.02111 (10)
N1	0.61990 (8)	0.35374 (18)	0.50879 (10)	0.0182 (3)
H1	0.5746 (13)	0.352 (3)	0.5401 (15)	0.026 (5)*
C2	0.68341 (9)	0.4285 (2)	0.54931 (12)	0.0195 (3)
C21	0.67203 (10)	0.5189 (3)	0.64282 (13)	0.0271 (4)
H21A	0.6433	0.4474	0.6864	0.060 (8)*
H21B	0.6430	0.6216	0.6320	0.043 (7)*
H21C	0.7225	0.5458	0.6701	0.048 (7)*
C3	0.75438 (10)	0.4191 (2)	0.50011 (13)	0.0230 (3)
H3	0.7997 (13)	0.470 (3)	0.5290 (16)	0.030 (5)*
C4	0.75726 (11)	0.3391 (2)	0.41113 (14)	0.0258 (4)
H4	0.8055 (14)	0.332 (3)	0.3788 (16)	0.030 (6)*
C5	0.69008 (11)	0.2682 (2)	0.37218 (13)	0.0238 (3)
H5	0.6899 (13)	0.214 (3)	0.3147 (16)	0.030 (6)*
C6	0.61975 (10)	0.2748 (2)	0.42278 (12)	0.0206 (3)
C61	0.54389 (11)	0.1994 (3)	0.38877 (15)	0.0317 (4)
H61A	0.5303	0.1046	0.4289	0.088 (11)*
H61B	0.5497	0.1618	0.3233	0.082 (10)*
H61C	0.5029	0.2832	0.3922	0.071 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01104 (13)	0.02169 (14)	0.01716 (14)	0.000	0.00110 (9)	0.000
Cl1	0.01537 (17)	0.0362 (2)	0.0273 (2)	0.00237 (15)	0.00065 (15)	0.01257 (17)
Cl2	0.01509 (17)	0.0278 (2)	0.02043 (19)	0.00431 (14)	0.00318 (13)	0.00174 (15)
N1	0.0146 (6)	0.0222 (6)	0.0177 (6)	−0.0015 (5)	0.0007 (5)	0.0016 (5)
C2	0.0171 (7)	0.0208 (7)	0.0205 (7)	−0.0025 (6)	−0.0027 (6)	0.0037 (6)
C21	0.0229 (8)	0.0342 (10)	0.0242 (9)	−0.0082 (7)	−0.0005 (7)	−0.0056 (7)
C3	0.0164 (7)	0.0260 (8)	0.0266 (8)	−0.0029 (6)	−0.0002 (6)	0.0062 (7)
C4	0.0199 (8)	0.0283 (9)	0.0291 (9)	0.0038 (7)	0.0074 (7)	0.0071 (7)
C5	0.0283 (8)	0.0230 (8)	0.0202 (8)	0.0053 (7)	0.0034 (7)	0.0025 (7)
C6	0.0229 (8)	0.0193 (8)	0.0196 (8)	0.0020 (6)	−0.0016 (6)	0.0005 (6)
C61	0.0251 (9)	0.0389 (10)	0.0312 (10)	−0.0028 (8)	−0.0042 (7)	−0.0115 (9)

Geometric parameters (Å, º)

Cu1—Cl1	2.2619 (4)	C3—C4	1.388 (3)
Cu1—Cl2	2.2409 (4)	C3—H3	0.95 (2)
N1—C6	1.346 (2)	C4—C5	1.379 (3)
N1—C2	1.351 (2)	C4—H4	0.93 (2)
N1—H1	0.88 (2)	C5—C6	1.385 (2)
C2—C3	1.386 (2)	C5—H5	0.90 (2)
C2—C21	1.493 (2)	C6—C61	1.494 (2)
C21—H21A	0.9600	C61—H61A	0.9600
C21—H21B	0.9600	C61—H61B	0.9600
C21—H21C	0.9600	C61—H61C	0.9600
Cl1—Cu1—Cl1^i	126.65 (3)	C2—C3—H3	118.0 (13)
Cl1—Cu1—Cl2	100.259 (15)	C4—C3—H3	122.4 (13)
Cl2—Cu1—Cl1^i	100.094 (15)	C3—C4—C5	120.27 (16)
Cl2—Cu1—Cl2^i	133.65 (3)	C3—C4—H4	119.1 (14)
C6—N1—C2	124.93 (15)	C5—C4—H4	120.6 (14)
C6—N1—H1	115.4 (14)	C4—C5—C6	119.82 (17)
C2—N1—H1	119.7 (14)	C4—C5—H5	122.7 (14)
N1—C2—C3	117.66 (15)	C6—C5—H5	117.5 (14)
N1—C2—C21	117.85 (14)	C5—C6—N1	117.72 (16)
C3—C2—C21	124.47 (15)	C5—C6—C61	124.51 (16)
C2—C21—H21A	109.5	N1—C6—C61	117.77 (15)
C2—C21—H21B	109.5	C6—C61—H61A	109.5
H21A—C21—H21B	109.5	C6—C61—H61B	109.5
C2—C21—H21C	109.5	H61A—C61—H61B	109.5
H21A—C21—H21C	109.5	C6—C61—H61C	109.5
H21B—C21—H21C	109.5	H61A—C61—H61C	109.5
C2—C3—C4	119.56 (16)	H61B—C61—H61C	109.5

Symmetry code: (i) −x+1, y, −z+3/2.

(26lutrtortho) bis(2,6-dimethylpyridinium) tetrachloridocuprate(II)

Crystal data

2(C7H10N)·Cl4Cu	Dx = 1.455 Mg m^−3
Mr = 421.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 2517 reflections
a = 16.9411 (5) Å	θ = 2.9–27.5°
b = 8.2218 (2) Å	µ = 1.68 mm^−1
c = 13.8212 (4) Å	T = 295 K
V = 1925.10 (9) Å^3	Irregular, yellow
Z = 4	0.29 × 0.25 × 0.10 mm
F(000) = 860

Data collection

KappaCCD diffractometer	2191 independent reflections
Radiation source: Enraf Nonius FR590	1732 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
Detector resolution: 9 pixels mm^-1	θmax = 27.4°, θmin = 4.5°
CCD rotation images, thick slices scans	h = −21→21
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −10→10
Tmin = 0.578, Tmax = 0.699	l = −17→17
36138 measured reflections

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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.5459P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2191 reflections	Δρmax = 0.27 e Å^−3
97 parameters	Δρmin = −0.56 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (12)

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	Occ. (<1)
Cu1	0.5000	0.20396 (5)	0.7500	0.04837 (17)
Cl1	0.45528 (4)	0.33340 (10)	0.61632 (5)	0.0764 (2)
Cl2	0.61154 (3)	0.09436 (8)	0.69429 (4)	0.0635 (2)
N1	0.62054 (11)	0.3521 (2)	0.50700 (13)	0.0527 (4)
H1	0.5765	0.3571	0.5377	0.063*
C2	0.68307 (13)	0.4265 (3)	0.54729 (18)	0.0588 (6)
C21	0.67045 (17)	0.5155 (4)	0.6396 (2)	0.0833 (8)
H21A	0.6161	0.5068	0.6584	0.125*	0.50
H21B	0.6839	0.6280	0.6309	0.125*	0.50
H21C	0.7033	0.4693	0.6891	0.125*	0.50
H21D	0.7194	0.5626	0.6606	0.125*	0.50
H21E	0.6516	0.4414	0.6880	0.125*	0.50
H21F	0.6322	0.6001	0.6298	0.125*	0.50
C3	0.75395 (15)	0.4146 (4)	0.4996 (2)	0.0751 (8)
H3	0.7991	0.4613	0.5258	0.090*
C4	0.75771 (19)	0.3334 (4)	0.4128 (3)	0.0869 (9)
H4	0.8055	0.3267	0.3800	0.104*
C5	0.6920 (2)	0.2624 (4)	0.3743 (2)	0.0781 (8)
H5	0.6951	0.2085	0.3153	0.094*
C6	0.62115 (16)	0.2707 (3)	0.42285 (18)	0.0621 (6)
C61	0.5459 (2)	0.1955 (5)	0.3898 (3)	0.0972 (11)
H61A	0.5051	0.2179	0.4360	0.146*	0.50
H61B	0.5528	0.0800	0.3839	0.146*	0.50
H61C	0.5314	0.2400	0.3281	0.146*	0.50
H61D	0.5544	0.1407	0.3294	0.146*	0.50
H61E	0.5067	0.2786	0.3814	0.146*	0.50
H61F	0.5281	0.1186	0.4373	0.146*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0331 (2)	0.0625 (3)	0.0495 (2)	0.000	0.00270 (13)	0.000
Cl1	0.0452 (3)	0.1076 (5)	0.0766 (4)	0.0081 (3)	0.0002 (3)	0.0347 (4)
Cl2	0.0449 (3)	0.0827 (4)	0.0629 (4)	0.0154 (3)	0.0107 (2)	0.0070 (3)
N1	0.0429 (9)	0.0637 (11)	0.0516 (10)	−0.0030 (8)	0.0012 (8)	0.0035 (9)
C2	0.0486 (12)	0.0643 (13)	0.0636 (14)	−0.0064 (10)	−0.0041 (10)	0.0142 (11)
C21	0.0732 (17)	0.100 (2)	0.0764 (18)	−0.0260 (16)	−0.0073 (14)	−0.0127 (16)
C3	0.0452 (13)	0.0883 (18)	0.092 (2)	−0.0092 (13)	0.0051 (13)	0.0244 (16)
C4	0.0631 (17)	0.098 (2)	0.100 (2)	0.0146 (16)	0.0331 (17)	0.0278 (19)
C5	0.091 (2)	0.0783 (17)	0.0653 (16)	0.0209 (16)	0.0198 (15)	0.0075 (14)
C6	0.0666 (15)	0.0633 (14)	0.0564 (14)	0.0089 (12)	−0.0001 (11)	0.0038 (11)
C61	0.087 (2)	0.118 (3)	0.087 (2)	−0.0065 (19)	−0.0150 (18)	−0.037 (2)

Geometric parameters (Å, º)

Cu1—Cl1	2.2628 (6)	C3—C4	1.374 (5)
Cu1—Cl2	2.2306 (5)	C3—H3	0.9300
N1—C6	1.342 (3)	C4—C5	1.364 (5)
N1—C2	1.344 (3)	C4—H4	0.9300
N1—H1	0.8600	C5—C6	1.377 (4)
C2—C3	1.374 (3)	C5—H5	0.9300
C2—C21	1.486 (4)	C6—C61	1.489 (4)
C21—H21A	0.9600	C61—H61A	0.9600
C21—H21B	0.9600	C61—H61B	0.9600
C21—H21C	0.9600	C61—H61C	0.9600
C21—H21D	0.9600	C61—H61D	0.9600
C21—H21E	0.9600	C61—H61E	0.9600
C21—H21F	0.9600	C61—H61F	0.9600
Cl1—Cu1—Cl1^i	123.89 (5)	C2—C3—H3	120.2
Cl1—Cu1—Cl2	101.06 (2)	C4—C3—H3	120.2
Cl1—Cu1—Cl2^i	100.85 (2)	C3—C4—C5	120.7 (3)
Cl2—Cu1—Cl2^i	132.35 (4)	C3—C4—H4	119.7
C6—N1—C2	125.5 (2)	C5—C4—H4	119.7
C6—N1—H1	117.3	C4—C5—C6	120.0 (3)
C2—N1—H1	117.3	C4—C5—H5	120.0
N1—C2—C3	117.2 (2)	C6—C5—H5	120.0
N1—C2—C21	117.8 (2)	C5—C6—N1	117.0 (3)
C3—C2—C21	125.0 (2)	C5—C6—C61	125.2 (3)
C2—C21—H21A	109.5	N1—C6—C61	117.8 (2)
C2—C21—H21B	109.5	C6—C61—H61A	109.5
H21A—C21—H21B	109.5	C6—C61—H61B	109.5
C2—C21—H21C	109.5	H61A—C61—H61B	109.5
H21A—C21—H21C	109.5	C6—C61—H61C	109.5
H21B—C21—H21C	109.5	H61A—C61—H61C	109.5
C2—C21—H21D	109.5	H61B—C61—H61C	109.5
C2—C21—H21E	109.5	C6—C61—H61D	109.5
H21D—C21—H21E	109.5	C6—C61—H61E	109.5
C2—C21—H21F	109.5	H61D—C61—H61E	109.5
H21D—C21—H21F	109.5	C6—C61—H61F	109.5
H21E—C21—H21F	109.5	H61D—C61—H61F	109.5
C2—C3—C4	119.6 (3)	H61E—C61—H61F	109.5

Symmetry code: (i) −x+1, y, −z+3/2.

(123tmpcubr4) bis(1,2,3-trimethylpyridnium) tetrabromidocuprate(II)

Crystal data

2(C8H12N)·Br4Cu	F(000) = 1212
Mr = 627.55	Dx = 1.932 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2599 reflections
a = 17.6373 (5) Å	θ = 2.9–27.5°
b = 9.4076 (4) Å	µ = 8.42 mm^−1
c = 14.7798 (5) Å	T = 295 K
β = 118.396 (2)°	Gem, dark purple
V = 2157.27 (13) Å^3	0.21 × 0.20 × 0.18 mm
Z = 4

Data collection

KappaCCD diffractometer	2461 independent reflections
Radiation source: Enraf Nonius FR590	1686 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 4.1°
CCD rotation images, thick slices scans	h = −22→20
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.164, Tmax = 0.217	l = 0→19
17272 measured reflections

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)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.025P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
2461 reflections	Δρmax = 0.49 e Å^−3
109 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.00071 (9)
Primary atom site location: structure-invariant direct methods

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
Cu1	0.5000	0.25273 (5)	0.2500	0.04301 (14)
Br1	0.53257 (2)	0.10011 (4)	0.39092 (3)	0.06197 (13)
Br2	0.60212 (2)	0.40953 (4)	0.23917 (2)	0.05737 (12)
N1	0.63304 (16)	0.6180 (3)	0.51335 (18)	0.0510 (6)
C11	0.5540 (2)	0.6974 (4)	0.4444 (3)	0.0770 (11)
H11B	0.5256	0.7284	0.4825	0.116*
H11A	0.5161	0.6368	0.3890	0.116*
H11C	0.5691	0.7786	0.4170	0.116*
C2	0.70149 (18)	0.6868 (3)	0.5891 (2)	0.0455 (7)
C21	0.6948 (2)	0.8438 (4)	0.5992 (3)	0.0619 (9)
H21B	0.6859	0.8898	0.5369	0.093*
H21C	0.7470	0.8785	0.6558	0.093*
H21A	0.6470	0.8641	0.6114	0.093*
C3	0.77380 (18)	0.6085 (3)	0.6547 (2)	0.0507 (8)
C31	0.8500 (2)	0.6775 (5)	0.7418 (3)	0.0839 (12)
H31A	0.8349	0.7066	0.7935	0.126*
H31B	0.8671	0.7591	0.7169	0.126*
H31C	0.8969	0.6110	0.7710	0.126*
C4	0.7744 (2)	0.4632 (4)	0.6402 (3)	0.0605 (9)
H4	0.8228	0.4099	0.6828	0.073*
C5	0.7035 (3)	0.3973 (4)	0.5625 (3)	0.0705 (10)
H5	0.7036	0.2997	0.5528	0.085*
C6	0.6339 (2)	0.4758 (4)	0.5008 (2)	0.0618 (9)
H6	0.5858	0.4314	0.4489	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0472 (3)	0.0334 (3)	0.0511 (3)	0	0.0256 (2)	0
Br1	0.0696 (2)	0.0502 (2)	0.0673 (2)	0.00868 (16)	0.03348 (18)	0.01943 (16)
Br2	0.0587 (2)	0.0521 (2)	0.0678 (2)	−0.01480 (15)	0.03527 (16)	−0.00349 (15)
N1	0.0554 (15)	0.0531 (17)	0.0457 (13)	0.0011 (13)	0.0251 (12)	−0.0025 (12)
C11	0.061 (2)	0.084 (3)	0.062 (2)	0.008 (2)	0.0084 (16)	0.001 (2)
C2	0.0485 (16)	0.0478 (19)	0.0452 (15)	0.0032 (14)	0.0263 (14)	0.0046 (13)
C21	0.065 (2)	0.051 (2)	0.066 (2)	−0.0035 (17)	0.0286 (17)	−0.0014 (17)
C3	0.0474 (17)	0.054 (2)	0.0538 (17)	0.0023 (15)	0.0264 (15)	0.0014 (15)
C31	0.057 (2)	0.093 (3)	0.078 (2)	0.000 (2)	0.0128 (19)	−0.003 (2)
C4	0.063 (2)	0.062 (2)	0.064 (2)	0.0178 (18)	0.0369 (18)	0.0094 (18)
C5	0.098 (3)	0.046 (2)	0.082 (2)	0.007 (2)	0.055 (2)	−0.0052 (19)
C6	0.072 (2)	0.057 (2)	0.0573 (19)	−0.0133 (19)	0.0313 (17)	−0.0156 (17)

Geometric parameters (Å, º)

Cu1—Br1	2.3646 (4)	C21—H21A	0.96
Cu1—Br2	2.3916 (4)	C3—C4	1.385 (5)
N1—C6	1.352 (4)	C3—C31	1.497 (4)
N1—C2	1.358 (4)	C31—H31A	0.96
N1—C11	1.479 (4)	C31—H31B	0.96
C11—H11B	0.96	C31—H31C	0.96
C11—H11A	0.96	C4—C5	1.379 (5)
C11—H11C	0.96	C4—H4	0.93
C2—C3	1.390 (4)	C5—C6	1.348 (5)
C2—C21	1.496 (4)	C5—H5	0.93
C21—H21B	0.96	C6—H6	0.93
C21—H21C	0.96
Br1—Cu1—Br1^i	105.23 (3)	H21B—C21—H21A	109.5
Br1—Cu1—Br2	123.933 (12)	H21C—C21—H21A	109.5
Br1—Cu1—Br2^i	100.999 (12)	C2—C3—C4	119.1 (3)
Br2—Cu1—Br2^i	103.84 (2)	C2—C3—C31	121.4 (3)
C6—N1—C2	121.4 (3)	C4—C3—C31	119.4 (3)
C6—N1—C11	118.3 (3)	C3—C31—H31A	109.5
C2—N1—C11	120.3 (3)	C3—C31—H31B	109.5
N1—C11—H11B	109.5	H31A—C31—H31B	109.5
N1—C11—H11A	109.5	C3—C31—H31C	109.5
H11B—C11—H11A	109.5	H31A—C31—H31C	109.5
N1—C11—H11C	109.5	H31B—C31—H31C	109.5
H11B—C11—H11C	109.5	C3—C4—C5	120.1 (3)
H11A—C11—H11C	109.5	C3—C4—H4	119.9
N1—C2—C3	119.0 (3)	C5—C4—H4	119.9
N1—C2—C21	118.1 (3)	C4—C5—C6	119.4 (3)
C3—C2—C21	122.9 (3)	C4—C5—H5	120.3
C2—C21—H21B	109.5	C6—C5—H5	120.3
C2—C21—H21C	109.5	C5—C6—N1	121.0 (3)
H21B—C21—H21C	109.5	C5—C6—H6	119.5
C2—C21—H21A	109.5	N1—C6—H6	119.5

Symmetry code: (i) −x+1, y, −z+1/2.

(nmphcucl4) bis(methyl(2-phenylethyl)ammonium tetrachloridocuprate(II)

Crystal data

2(C9H14N^+)·(C14Cu^2^−)	F(000) = 494
Mr = 477.76	Dx = 1.45 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3915 reflections
a = 6.4234 (1) Å	θ = 1–32.0°
b = 22.4819 (4) Å	µ = 1.49 mm^−1
c = 8.4552 (1) Å	T = 100 K
β = 116.314 (1)°	Rod, dark green
V = 1094.49 (3) Å^3	0.18 × 0.06 × 0.04 mm
Z = 2

Data collection

KappaCCD diffractometer	3814 independent reflections
Radiation source: Enraf Nonius FR590	3186 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 9 pixels mm^-1	θmax = 32.0°, θmin = 3.2°
CCD rotation images, thick slices scans	h = −9→9
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −33→33
Tmin = 0.870, Tmax = 0.954	l = −12→12
3814 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.057	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0207P)^2 + 0.1059P] where P = (Fo^2 + 2Fc^2)/3
3814 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.51 e Å^−3
0 constraints

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
Cu1	0	0	0	0.01156 (5)
Cl1	−0.22895 (4)	−0.042521 (11)	0.10657 (3)	0.01423 (6)
Cl2	0.10995 (4)	0.071176 (13)	0.21497 (4)	0.01842 (7)
C1	0.3837 (2)	0.27495 (6)	0.13980 (16)	0.0210 (2)
H1	0.237 (3)	0.2550 (6)	0.0950 (19)	0.025 (4)*
C2	0.3916 (2)	0.33518 (6)	0.17589 (16)	0.0245 (3)
H2	0.256 (3)	0.3559 (8)	0.157 (2)	0.038 (4)*
C3	0.6017 (2)	0.36514 (6)	0.24559 (16)	0.0233 (3)
H3	0.606 (3)	0.4046 (7)	0.274 (2)	0.031 (4)*
C4	0.8038 (2)	0.33486 (6)	0.27757 (16)	0.0227 (2)
H4	0.945 (3)	0.3540 (8)	0.329 (2)	0.036 (4)*
C5	0.7958 (2)	0.27460 (5)	0.23977 (15)	0.0191 (2)
H5	0.931 (3)	0.2539 (7)	0.260 (2)	0.025 (4)*
C6	0.58655 (19)	0.24371 (5)	0.17151 (14)	0.0159 (2)
C7	0.5811 (2)	0.17769 (5)	0.13885 (15)	0.0194 (2)
H7A	0.425 (3)	0.1656 (6)	0.0577 (19)	0.025 (4)*
H7B	0.681 (2)	0.1673 (6)	0.0894 (19)	0.023 (4)*
C8	0.65191 (19)	0.14323 (5)	0.30936 (14)	0.0147 (2)
H8A	0.547 (2)	0.1494 (6)	0.3587 (18)	0.016 (3)*
H8B	0.805 (2)	0.1538 (6)	0.3945 (18)	0.018 (3)*
N9	0.65539 (16)	0.07808 (4)	0.27732 (12)	0.01320 (17)
H9A	0.523 (3)	0.0694 (6)	0.1929 (19)	0.020 (4)*
H9B	0.764 (3)	0.0706 (6)	0.2383 (18)	0.021 (4)*
C10	0.7111 (2)	0.04144 (5)	0.43702 (15)	0.0172 (2)
H10A	0.598 (2)	0.0473 (6)	0.4812 (18)	0.015 (3)*
H10B	0.858 (3)	0.0539 (6)	0.5284 (19)	0.021 (4)*
H10C	0.707 (3)	0.0019 (7)	0.406 (2)	0.023 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.00979 (8)	0.01237 (10)	0.01223 (9)	−0.00022 (6)	0.00461 (7)	−0.00077 (7)
Cl1	0.01506 (11)	0.01371 (13)	0.01529 (12)	−0.00153 (9)	0.00798 (9)	−0.00092 (9)
Cl2	0.01590 (12)	0.02184 (14)	0.02062 (13)	−0.00645 (10)	0.01090 (10)	−0.00890 (10)
C1	0.0185 (5)	0.0257 (6)	0.0169 (5)	−0.0029 (5)	0.0061 (4)	−0.0025 (5)
C2	0.0285 (6)	0.0264 (7)	0.0179 (6)	0.0083 (5)	0.0096 (5)	0.0018 (5)
C3	0.0397 (7)	0.0149 (6)	0.0169 (5)	−0.0001 (5)	0.0140 (5)	0.0007 (5)
C4	0.0291 (6)	0.0207 (6)	0.0189 (6)	−0.0091 (5)	0.0113 (5)	−0.0011 (5)
C5	0.0197 (5)	0.0204 (6)	0.0175 (5)	−0.0011 (4)	0.0087 (4)	0.0014 (4)
C6	0.0210 (5)	0.0156 (5)	0.0110 (5)	−0.0018 (4)	0.0069 (4)	0.0003 (4)
C7	0.0266 (6)	0.0163 (5)	0.0144 (5)	−0.0030 (4)	0.0083 (5)	−0.0022 (4)
C8	0.0165 (5)	0.0135 (5)	0.0146 (5)	−0.0020 (4)	0.0074 (4)	−0.0026 (4)
N9	0.0121 (4)	0.0143 (4)	0.0132 (4)	−0.0009 (3)	0.0056 (3)	−0.0015 (3)
C10	0.0198 (5)	0.0163 (6)	0.0162 (5)	0.0014 (4)	0.0086 (4)	0.0012 (4)

Geometric parameters (Å, º)

Cu1—Cl1	2.2502 (2)	C6—C7	1.5074 (16)
Cu1—Cl2	2.2858 (3)	C7—C8	1.5179 (16)
C6—C1	1.3974 (16)	C7—H7A	0.971 (15)
C1—C2	1.3840 (18)	C7—H7B	0.936 (14)
C1—H1	0.960 (15)	C8—N9	1.4914 (15)
C2—C3	1.3845 (19)	C8—H8A	0.947 (13)
C2—H2	0.938 (17)	C8—H8B	0.956 (14)
C3—C4	1.3822 (19)	N9—C10	1.4838 (14)
C3—H3	0.917 (16)	N9—H9A	0.855 (15)
C4—C5	1.3878 (18)	N9—H9B	0.912 (14)
C4—H4	0.921 (17)	C10—H10A	0.960 (13)
C5—C6	1.3906 (16)	C10—H10B	0.960 (15)
C5—H5	0.930 (15)	C10—H10C	0.924 (15)
Cl1—Cu1—Cl2	90.309 (9)	C6—C7—H7B	111.2 (9)
C6—C1—C2	120.63 (11)	C8—C7—H7B	108.7 (9)
C6—C1—H1	120.8 (9)	H7A—C7—H7B	108.3 (12)
C2—C1—H1	118.6 (9)	C7—C8—N9	110.55 (9)
C1—C2—C3	120.22 (12)	C7—C8—H8A	111.8 (8)
C1—C2—H2	120.5 (10)	N9—C8—H8A	107.2 (8)
C3—C2—H2	119.3 (10)	C7—C8—H8B	111.3 (8)
C2—C3—C4	119.83 (12)	N9—C8—H8B	106.7 (8)
C2—C3—H3	119.5 (10)	H8A—C8—H8B	109.1 (11)
C4—C3—H3	120.6 (10)	C8—N9—C10	113.39 (9)
C3—C4—C5	120.00 (12)	C8—N9—H9A	106.7 (10)
C3—C4—H4	120.5 (10)	C10—N9—H9A	112.5 (10)
C5—C4—H4	119.4 (11)	C8—N9—H9B	108.8 (9)
C4—C5—C6	120.89 (11)	C10—N9—H9B	108.2 (9)
C4—C5—H5	120.6 (9)	H9A—N9—H9B	107.0 (13)
C6—C5—H5	118.6 (9)	N9—C10—H10A	111.0 (8)
C5—C6—C1	118.43 (11)	N9—C10—H10B	109.0 (8)
C5—C6—C7	120.50 (11)	H10A—C10—H10B	106.9 (11)
C1—C6—C7	121.04 (11)	N9—C10—H10C	108.3 (10)
C6—C7—C8	110.84 (9)	H10A—C10—H10C	108.0 (12)
C6—C7—H7A	109.7 (9)	H10B—C10—H10C	113.7 (13)
C8—C7—H7A	108.0 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9A···Cl1^i	0.855 (13)	2.471 (13)	3.286 (1)	159.6 (14)
N9—H9A···Cl2	0.855 (13)	2.744 (19)	3.307 (1)	124.9 (14)
N9—H9B···Cl2^ii	0.912 (19)	2.314 (18)	3.193 (1)	161.7 (15)
N9—H9B···Cl1^ii	0.912 (19)	2.785 (15)	3.307 (1)	117.6 (11)

Symmetry codes: (i) −x, −y, −z; (ii) x+1, y, z.