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The title compound, [CuCl2(C11H24N2)], crystallizes as four-coordinate monomers with distorted square-planar geometry. The complex is chiral and forms racemic crystals. Molecules which have an S-configuration at nitro­gen have a λ-conformation of the five-membered chelate ring, and those with R-configuration have a δ-conformation. The title compound forms infinite one-dimensional chains via weak intermolecular Cl...H—C hydrogen contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015909/rn6018sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015909/rn6018Isup2.hkl
Contains datablock I

CCDC reference: 248716

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.107
  • Data-to-parameter ratio = 27.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 6.86 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Cu1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear(Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 1990); software used to prepare material for publication: SHELXL97.

Dichloro(N-cyclohexyl-N,N',N'-trimethylethylenediamine)copper(II) top
Crystal data top
[CuCl2(C11H24N2)]F(000) = 668
Mr = 318.76Dx = 1.451 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 13113 reflections
a = 7.8173 (19) Åθ = 2.4–31.9°
b = 19.979 (4) ŵ = 1.84 mm1
c = 9.3411 (18) ÅT = 293 K
β = 91.004 (9)°Needle, blue
V = 1458.7 (5) Å30.5 × 0.2 × 0.2 mm
Z = 4
Data collection top
Rigaku R-AXIS IIC image-plate system
diffractometer
4020 independent reflections
Radiation source: rotating anode, Rigaku RU2003372 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 105 pixels mm-1θmax = 31.9°, θmin = 2.4°
φ scansh = 1010
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2000)
k = 2728
Tmin = 0.493, Tmax = 0.692l = 1212
13113 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0486P)2 + 0.3327P]
where P = (Fo2 + 2Fc2)/3
4020 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.45 e Å3
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.97114 (3)0.195636 (12)0.52747 (3)0.03501 (10)
Cl11.18006 (8)0.27060 (3)0.57066 (7)0.05398 (17)
Cl21.15715 (9)0.11305 (4)0.49474 (11)0.0726 (2)
N10.7905 (2)0.26964 (9)0.5139 (2)0.0407 (4)
N20.7649 (2)0.13061 (9)0.5334 (2)0.0394 (4)
C10.8300 (4)0.32215 (14)0.4081 (3)0.0585 (7)
H1A0.93420.34440.43600.088*
H1B0.73820.35400.40390.088*
H1C0.84340.30210.31550.088*
C20.7713 (4)0.30098 (14)0.6569 (3)0.0617 (7)
H2A0.74720.26700.72630.092*
H2B0.67900.33260.65330.092*
H2C0.87550.32360.68360.092*
C30.6294 (3)0.23650 (13)0.4690 (3)0.0497 (6)
H3A0.63060.22770.36700.060*
H3B0.53330.26570.48830.060*
C40.6098 (3)0.17200 (14)0.5491 (3)0.0499 (6)
H4A0.59170.18130.64960.060*
H4B0.51090.14790.51200.060*
C50.7555 (4)0.09483 (15)0.3935 (3)0.0632 (7)
H5A0.85620.06790.38270.095*
H5B0.74840.12690.31710.095*
H5C0.65600.06670.39060.095*
C60.7880 (3)0.08169 (11)0.6536 (2)0.0401 (4)
H60.87980.05100.62650.048*
C70.6303 (3)0.03903 (13)0.6819 (3)0.0563 (6)
H7A0.53530.06780.70630.068*
H7B0.59870.01450.59580.068*
C80.6651 (4)0.01010 (14)0.8037 (4)0.0643 (8)
H8A0.56170.03520.82280.077*
H8B0.75270.04160.77550.077*
C90.7227 (4)0.02577 (15)0.9375 (3)0.0611 (7)
H9A0.74830.00671.01210.073*
H9B0.63140.05450.97040.073*
C100.8804 (4)0.06759 (16)0.9096 (3)0.0614 (7)
H10A0.91300.09160.99600.074*
H10B0.97440.03850.88440.074*
C110.8471 (3)0.11701 (12)0.7895 (3)0.0456 (5)
H11A0.95100.14180.77100.055*
H11B0.76020.14870.81840.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02851 (14)0.03873 (15)0.03798 (15)0.00244 (9)0.00555 (9)0.00167 (10)
Cl10.0419 (3)0.0602 (4)0.0597 (4)0.0165 (3)0.0007 (2)0.0013 (3)
Cl20.0452 (3)0.0568 (4)0.1169 (7)0.0090 (3)0.0270 (4)0.0073 (4)
N10.0373 (9)0.0404 (10)0.0446 (10)0.0017 (7)0.0035 (7)0.0047 (8)
N20.0358 (8)0.0415 (9)0.0410 (10)0.0066 (7)0.0024 (7)0.0019 (8)
C10.0569 (15)0.0531 (14)0.0655 (18)0.0036 (12)0.0013 (12)0.0201 (13)
C20.0734 (19)0.0549 (15)0.0570 (17)0.0176 (13)0.0077 (13)0.0098 (12)
C30.0304 (10)0.0609 (15)0.0579 (15)0.0000 (10)0.0013 (9)0.0137 (12)
C40.0283 (10)0.0611 (14)0.0604 (15)0.0060 (10)0.0014 (9)0.0117 (12)
C50.0768 (18)0.0695 (18)0.0433 (14)0.0263 (15)0.0010 (12)0.0129 (13)
C60.0367 (10)0.0367 (10)0.0471 (12)0.0038 (8)0.0057 (8)0.0005 (9)
C70.0566 (14)0.0517 (14)0.0607 (16)0.0219 (12)0.0039 (11)0.0033 (12)
C80.0686 (17)0.0459 (14)0.079 (2)0.0112 (13)0.0176 (14)0.0124 (13)
C90.0588 (15)0.0608 (16)0.0639 (18)0.0065 (13)0.0111 (12)0.0240 (14)
C100.0568 (15)0.0682 (17)0.0591 (17)0.0006 (13)0.0041 (12)0.0184 (14)
C110.0471 (12)0.0447 (12)0.0449 (13)0.0047 (10)0.0014 (9)0.0028 (10)
Geometric parameters (Å, º) top
Cu1—N12.0471 (19)C5—H5A0.9600
Cu1—N22.0722 (18)C5—H5B0.9600
Cu1—Cl22.2239 (8)C5—H5C0.9600
Cu1—Cl12.2472 (7)C6—C111.517 (3)
N1—C31.477 (3)C6—C71.526 (3)
N1—C11.478 (3)C6—H60.9800
N1—C21.486 (3)C7—C81.524 (4)
N2—C41.477 (3)C7—H7A0.9700
N2—C51.490 (3)C7—H7B0.9700
N2—C61.497 (3)C8—C91.503 (5)
C1—H1A0.9600C8—H8A0.9700
C1—H1B0.9600C8—H8B0.9700
C1—H1C0.9600C9—C101.515 (4)
C2—H2A0.9600C9—H9A0.9700
C2—H2B0.9600C9—H9B0.9700
C2—H2C0.9600C10—C111.514 (4)
C3—C41.499 (3)C10—H10A0.9700
C3—H3A0.9700C10—H10B0.9700
C3—H3B0.9700C11—H11A0.9700
C4—H4A0.9700C11—H11B0.9700
C4—H4B0.9700
N1—Cu1—N285.31 (8)N2—C5—H5A109.5
N1—Cu1—Cl2168.35 (6)N2—C5—H5B109.5
N2—Cu1—Cl292.84 (6)H5A—C5—H5B109.5
N1—Cu1—Cl191.62 (6)N2—C5—H5C109.5
N2—Cu1—Cl1167.53 (6)H5A—C5—H5C109.5
Cl2—Cu1—Cl192.54 (3)H5B—C5—H5C109.5
C3—N1—C1108.42 (19)N2—C6—C11110.79 (18)
C3—N1—C2110.2 (2)N2—C6—C7114.00 (19)
C1—N1—C2109.1 (2)C11—C6—C7110.5 (2)
C3—N1—Cu1106.12 (14)N2—C6—H6107.1
C1—N1—Cu1113.70 (16)C11—C6—H6107.1
C2—N1—Cu1109.20 (16)C7—C6—H6107.1
C4—N2—C5109.1 (2)C8—C7—C6110.8 (2)
C4—N2—C6112.31 (17)C8—C7—H7A109.5
C5—N2—C6110.37 (19)C6—C7—H7A109.5
C4—N2—Cu1106.99 (14)C8—C7—H7B109.5
C5—N2—Cu1107.66 (14)C6—C7—H7B109.5
C6—N2—Cu1110.21 (13)H7A—C7—H7B108.1
N1—C1—H1A109.5C9—C8—C7111.2 (2)
N1—C1—H1B109.5C9—C8—H8A109.4
H1A—C1—H1B109.5C7—C8—H8A109.4
N1—C1—H1C109.5C9—C8—H8B109.4
H1A—C1—H1C109.5C7—C8—H8B109.4
H1B—C1—H1C109.5H8A—C8—H8B108.0
N1—C2—H2A109.5C8—C9—C10110.7 (2)
N1—C2—H2B109.5C8—C9—H9A109.5
H2A—C2—H2B109.5C10—C9—H9A109.5
N1—C2—H2C109.5C8—C9—H9B109.5
H2A—C2—H2C109.5C10—C9—H9B109.5
H2B—C2—H2C109.5H9A—C9—H9B108.1
N1—C3—C4109.77 (19)C11—C10—C9110.9 (2)
N1—C3—H3A109.7C11—C10—H10A109.5
C4—C3—H3A109.7C9—C10—H10A109.5
N1—C3—H3B109.7C11—C10—H10B109.5
C4—C3—H3B109.7C9—C10—H10B109.5
H3A—C3—H3B108.2H10A—C10—H10B108.0
N2—C4—C3109.90 (18)C10—C11—C6111.3 (2)
N2—C4—H4A109.7C10—C11—H11A109.4
C3—C4—H4A109.7C6—C11—H11A109.4
N2—C4—H4B109.7C10—C11—H11B109.4
C3—C4—H4B109.7C6—C11—H11B109.4
H4A—C4—H4B108.2H11A—C11—H11B108.0
 

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