Crystal structure of bis­(N,N,N′,N′-tetra­methyl­guanidinium) tetra­chlorido­cuprate(II)

The crystal structure of bis­(tetra­methyl­guanidinium) tetra­chlorido­cuprate(II) contains distorted tetra­hedral [CuCl₄]²⁻ anions and tetra­methyl­guanidinium cations held together through N—H...Cl and C—H...Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](N-C) = 0.003 Å
• R factor = 0.028
• wR factor = 0.071
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.40 Report
PLAT420_ALERT_2_C D-H Without Acceptor       N2     --  H2A    ...     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2C    ..  CL1     ..       2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2D    ..  CL1     ..       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2E    ..  CL2     ..       2.85 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.         12 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Bis(N,N,N',N'-tetramethylguanidinium) tetrachloridocuprate(II)

Crystal data

(C5H14N3)2[CuCl4]	F(000) = 908
Mr = 437.72	Dx = 1.515 Mg m^−3
Monoclinic, C2/c	Ga Kα radiation, λ = 1.34139 Å
a = 18.9274 (5) Å	Cell parameters from 9968 reflections
b = 8.2441 (2) Å	θ = 4.9–60.7°
c = 14.8654 (4) Å	µ = 9.51 mm^−1
β = 124.165 (1)°	T = 100 K
V = 1919.28 (9) Å^3	Block, clear yellowish green
Z = 4	0.16 × 0.10 × 0.06 mm

Data collection

Bruker Venture Metaljet diffractometer	2208 independent reflections
Radiation source: Metal Jet, Gallium Liquid Metal Jet Source	2178 reflections with I > 2σ(I)
Helios MX Mirror Optics monochromator	Rint = 0.036
Detector resolution: 10.24 pixels mm^-1	θmax = 60.7°, θmin = 4.9°
ω and φ scans	h = −24→24
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −10→10
Tmin = 0.449, Tmax = 0.752	l = −16→19
14222 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	All H-atom parameters refined
wR(F^2) = 0.071	w = 1/[σ^2(Fo^2) + (0.0315P)^2 + 2.7253P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
2208 reflections	Δρmax = 0.84 e Å^−3
152 parameters	Δρmin = −0.35 e Å^−3
0 restraints

Special details

Experimental. X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.18244 (9)	0.33219 (19)	0.30111 (11)	0.0202 (3)
N2	0.24981 (11)	0.5129 (2)	0.44495 (13)	0.0277 (4)
N3	0.32977 (9)	0.32615 (17)	0.42260 (11)	0.0164 (3)
C1	0.25428 (10)	0.3903 (2)	0.38962 (13)	0.0173 (3)
C2	0.17917 (12)	0.2676 (2)	0.20725 (14)	0.0215 (3)
C3	0.09950 (12)	0.3500 (3)	0.28512 (17)	0.0314 (4)
C4	0.40978 (11)	0.4132 (2)	0.49381 (15)	0.0235 (4)
C5	0.33922 (12)	0.1564 (2)	0.40153 (15)	0.0208 (3)
Cu1	0.5000	0.71829 (4)	0.7500	0.01698 (11)
Cl1	0.37443 (3)	0.61496 (7)	0.70754 (4)	0.03106 (13)
Cl2	0.54835 (3)	0.82595 (5)	0.91317 (3)	0.02989 (13)
H4A	0.4363 (15)	0.380 (3)	0.569 (2)	0.030 (6)*
H5A	0.2894 (16)	0.099 (3)	0.3780 (19)	0.029 (6)*
H4B	0.4000 (14)	0.526 (3)	0.4851 (18)	0.024 (5)*
H2C	0.1702 (16)	0.150 (3)	0.2047 (19)	0.030 (6)*
H2D	0.2285 (15)	0.291 (3)	0.2132 (18)	0.022 (5)*
H3A	0.0693 (18)	0.248 (4)	0.260 (2)	0.040 (7)*
H2A	0.2102 (18)	0.568 (4)	0.418 (2)	0.037 (7)*
H3B	0.0655 (19)	0.432 (4)	0.228 (2)	0.050 (8)*
H5B	0.3539 (15)	0.147 (3)	0.349 (2)	0.028 (6)*
H5C	0.3857 (16)	0.111 (3)	0.465 (2)	0.028 (6)*
H2E	0.1316 (16)	0.319 (3)	0.143 (2)	0.028 (6)*
H4C	0.4454 (16)	0.389 (3)	0.468 (2)	0.033 (6)*
H2B	0.2934 (17)	0.536 (3)	0.509 (2)	0.035 (6)*
H3C	0.1050 (17)	0.373 (3)	0.352 (2)	0.040 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0176 (6)	0.0242 (7)	0.0155 (6)	0.0023 (6)	0.0072 (5)	−0.0054 (6)
N2	0.0225 (7)	0.0289 (8)	0.0186 (7)	0.0092 (7)	0.0036 (6)	−0.0097 (6)
N3	0.0174 (6)	0.0135 (6)	0.0163 (6)	−0.0003 (5)	0.0083 (5)	−0.0008 (5)
C1	0.0196 (7)	0.0167 (7)	0.0130 (7)	0.0028 (6)	0.0075 (6)	−0.0001 (6)
C2	0.0273 (9)	0.0215 (9)	0.0134 (8)	−0.0026 (7)	0.0102 (7)	−0.0044 (6)
C3	0.0182 (8)	0.0432 (12)	0.0264 (9)	0.0061 (8)	0.0086 (7)	−0.0100 (9)
C4	0.0194 (8)	0.0228 (9)	0.0223 (8)	−0.0040 (7)	0.0079 (7)	−0.0029 (7)
C5	0.0234 (8)	0.0132 (7)	0.0253 (9)	0.0028 (7)	0.0135 (7)	0.0000 (7)
Cu1	0.01872 (18)	0.01483 (18)	0.01209 (17)	0.000	0.00542 (14)	0.000
Cl1	0.0201 (2)	0.0510 (3)	0.0243 (2)	−0.00970 (18)	0.01383 (17)	−0.01532 (19)
Cl2	0.0501 (3)	0.0180 (2)	0.01273 (19)	−0.00519 (18)	0.01222 (18)	−0.00224 (14)

Geometric parameters (Å, º)

N1—C1	1.342 (2)	C3—H3B	0.99 (3)
N1—C2	1.462 (2)	C3—H3C	0.96 (3)
N1—C3	1.457 (2)	C4—H4A	0.97 (3)
N2—C1	1.335 (2)	C4—H4B	0.95 (2)
N2—H2A	0.77 (3)	C4—H4C	0.97 (3)
N2—H2B	0.86 (3)	C5—H5A	0.93 (3)
N3—C1	1.332 (2)	C5—H5B	0.96 (2)
N3—C4	1.459 (2)	C5—H5C	0.93 (3)
N3—C5	1.467 (2)	Cu1—Cl1^i	2.2557 (4)
C2—H2C	0.98 (3)	Cu1—Cl1	2.2557 (4)
C2—H2D	0.91 (2)	Cu1—Cl2^i	2.2396 (4)
C2—H2E	0.96 (3)	Cu1—Cl2	2.2396 (4)
C3—H3A	0.96 (3)
C1—N1—C2	122.85 (14)	H3A—C3—H3B	108 (2)
C1—N1—C3	121.97 (14)	H3A—C3—H3C	105 (2)
C3—N1—C2	114.63 (14)	H3B—C3—H3C	113 (2)
C1—N2—H2A	120 (2)	N3—C4—H4A	110.4 (14)
C1—N2—H2B	119.9 (17)	N3—C4—H4B	110.0 (14)
H2A—N2—H2B	120 (3)	N3—C4—H4C	106.3 (15)
C1—N3—C4	122.24 (14)	H4A—C4—H4B	112 (2)
C1—N3—C5	122.31 (14)	H4A—C4—H4C	112 (2)
C4—N3—C5	115.01 (14)	H4B—C4—H4C	106 (2)
N2—C1—N1	119.64 (15)	N3—C5—H5A	110.2 (15)
N3—C1—N1	120.38 (15)	N3—C5—H5B	111.8 (15)
N3—C1—N2	119.98 (15)	N3—C5—H5C	109.2 (15)
N1—C2—H2C	108.1 (14)	H5A—C5—H5B	110 (2)
N1—C2—H2D	109.8 (14)	H5A—C5—H5C	111 (2)
N1—C2—H2E	107.2 (15)	H5B—C5—H5C	104 (2)
H2C—C2—H2D	111 (2)	Cl1—Cu1—Cl1^i	135.62 (3)
H2C—C2—H2E	110 (2)	Cl2—Cu1—Cl1	100.265 (17)
H2D—C2—H2E	110 (2)	Cl2^i—Cu1—Cl1	96.958 (19)
N1—C3—H3A	109.1 (16)	Cl2—Cu1—Cl1^i	96.959 (19)
N1—C3—H3B	109.1 (17)	Cl2^i—Cu1—Cl1^i	100.264 (17)
N1—C3—H3C	111.8 (16)	Cl2—Cu1—Cl2^i	133.31 (3)
C2—N1—C1—N2	146.94 (18)	C4—N3—C1—N1	159.80 (16)
C2—N1—C1—N3	−33.3 (3)	C4—N3—C1—N2	−20.4 (2)
C3—N1—C1—N2	−24.1 (3)	C5—N3—C1—N1	−28.2 (2)
C3—N1—C1—N3	155.67 (18)	C5—N3—C1—N2	151.61 (17)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···Cl2^i	0.95 (2)	2.77 (2)	3.5902 (19)	145.3 (18)
C2—H2C···Cl1^ii	0.98 (3)	2.90 (3)	3.745 (2)	144.5 (18)
C2—H2D···Cl1^iii	0.91 (2)	2.91 (2)	3.818 (2)	173.3 (19)
C3—H3B···Cl2^iv	0.99 (3)	2.82 (3)	3.793 (2)	168 (2)
C5—H5C···Cl2^v	0.93 (3)	2.80 (3)	3.5992 (18)	144.9 (19)
C2—H2E···Cl2^vi	0.96 (3)	2.85 (3)	3.6491 (18)	140.5 (19)
N2—H2B···Cl1	0.86 (3)	2.53 (3)	3.3417 (16)	157 (2)

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