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The title compound, [CuCl
2(C
11H
24N
2)], 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
CCDC reference: 248716
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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 = 318.76 | Dx = 1.451 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 13113 reflections |
a = 7.8173 (19) Å | θ = 2.4–31.9° |
b = 19.979 (4) Å | µ = 1.84 mm−1 |
c = 9.3411 (18) Å | T = 293 K |
β = 91.004 (9)° | Needle, blue |
V = 1458.7 (5) Å3 | 0.5 × 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 RU200 | 3372 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
Detector resolution: 105 pixels mm-1 | θmax = 31.9°, θmin = 2.4° |
φ scans | h = −10→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000) | k = −27→28 |
Tmin = 0.493, Tmax = 0.692 | l = −12→12 |
13113 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-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 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.97114 (3) | 0.195636 (12) | 0.52747 (3) | 0.03501 (10) | |
Cl1 | 1.18006 (8) | 0.27060 (3) | 0.57066 (7) | 0.05398 (17) | |
Cl2 | 1.15715 (9) | 0.11305 (4) | 0.49474 (11) | 0.0726 (2) | |
N1 | 0.7905 (2) | 0.26964 (9) | 0.5139 (2) | 0.0407 (4) | |
N2 | 0.7649 (2) | 0.13061 (9) | 0.5334 (2) | 0.0394 (4) | |
C1 | 0.8300 (4) | 0.32215 (14) | 0.4081 (3) | 0.0585 (7) | |
H1A | 0.9342 | 0.3444 | 0.4360 | 0.088* | |
H1B | 0.7382 | 0.3540 | 0.4039 | 0.088* | |
H1C | 0.8434 | 0.3021 | 0.3155 | 0.088* | |
C2 | 0.7713 (4) | 0.30098 (14) | 0.6569 (3) | 0.0617 (7) | |
H2A | 0.7472 | 0.2670 | 0.7263 | 0.092* | |
H2B | 0.6790 | 0.3326 | 0.6533 | 0.092* | |
H2C | 0.8755 | 0.3236 | 0.6836 | 0.092* | |
C3 | 0.6294 (3) | 0.23650 (13) | 0.4690 (3) | 0.0497 (6) | |
H3A | 0.6306 | 0.2277 | 0.3670 | 0.060* | |
H3B | 0.5333 | 0.2657 | 0.4883 | 0.060* | |
C4 | 0.6098 (3) | 0.17200 (14) | 0.5491 (3) | 0.0499 (6) | |
H4A | 0.5917 | 0.1813 | 0.6496 | 0.060* | |
H4B | 0.5109 | 0.1479 | 0.5120 | 0.060* | |
C5 | 0.7555 (4) | 0.09483 (15) | 0.3935 (3) | 0.0632 (7) | |
H5A | 0.8562 | 0.0679 | 0.3827 | 0.095* | |
H5B | 0.7484 | 0.1269 | 0.3171 | 0.095* | |
H5C | 0.6560 | 0.0667 | 0.3906 | 0.095* | |
C6 | 0.7880 (3) | 0.08169 (11) | 0.6536 (2) | 0.0401 (4) | |
H6 | 0.8798 | 0.0510 | 0.6265 | 0.048* | |
C7 | 0.6303 (3) | 0.03903 (13) | 0.6819 (3) | 0.0563 (6) | |
H7A | 0.5353 | 0.0678 | 0.7063 | 0.068* | |
H7B | 0.5987 | 0.0145 | 0.5958 | 0.068* | |
C8 | 0.6651 (4) | −0.01010 (14) | 0.8037 (4) | 0.0643 (8) | |
H8A | 0.5617 | −0.0352 | 0.8228 | 0.077* | |
H8B | 0.7527 | −0.0416 | 0.7755 | 0.077* | |
C9 | 0.7227 (4) | 0.02577 (15) | 0.9375 (3) | 0.0611 (7) | |
H9A | 0.7483 | −0.0067 | 1.0121 | 0.073* | |
H9B | 0.6314 | 0.0545 | 0.9704 | 0.073* | |
C10 | 0.8804 (4) | 0.06759 (16) | 0.9096 (3) | 0.0614 (7) | |
H10A | 0.9130 | 0.0916 | 0.9960 | 0.074* | |
H10B | 0.9744 | 0.0385 | 0.8844 | 0.074* | |
C11 | 0.8471 (3) | 0.11701 (12) | 0.7895 (3) | 0.0456 (5) | |
H11A | 0.9510 | 0.1418 | 0.7710 | 0.055* | |
H11B | 0.7602 | 0.1487 | 0.8184 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02851 (14) | 0.03873 (15) | 0.03798 (15) | −0.00244 (9) | 0.00555 (9) | −0.00167 (10) |
Cl1 | 0.0419 (3) | 0.0602 (4) | 0.0597 (4) | −0.0165 (3) | −0.0007 (2) | 0.0013 (3) |
Cl2 | 0.0452 (3) | 0.0568 (4) | 0.1169 (7) | 0.0090 (3) | 0.0270 (4) | −0.0073 (4) |
N1 | 0.0373 (9) | 0.0404 (10) | 0.0446 (10) | 0.0017 (7) | 0.0035 (7) | 0.0047 (8) |
N2 | 0.0358 (8) | 0.0415 (9) | 0.0410 (10) | −0.0066 (7) | 0.0024 (7) | −0.0019 (8) |
C1 | 0.0569 (15) | 0.0531 (14) | 0.0655 (18) | −0.0036 (12) | −0.0013 (12) | 0.0201 (13) |
C2 | 0.0734 (19) | 0.0549 (15) | 0.0570 (17) | 0.0176 (13) | 0.0077 (13) | −0.0098 (12) |
C3 | 0.0304 (10) | 0.0609 (15) | 0.0579 (15) | 0.0000 (10) | −0.0013 (9) | 0.0137 (12) |
C4 | 0.0283 (10) | 0.0611 (14) | 0.0604 (15) | −0.0060 (10) | 0.0014 (9) | 0.0117 (12) |
C5 | 0.0768 (18) | 0.0695 (18) | 0.0433 (14) | −0.0263 (15) | 0.0010 (12) | −0.0129 (13) |
C6 | 0.0367 (10) | 0.0367 (10) | 0.0471 (12) | −0.0038 (8) | 0.0057 (8) | 0.0005 (9) |
C7 | 0.0566 (14) | 0.0517 (14) | 0.0607 (16) | −0.0219 (12) | 0.0039 (11) | 0.0033 (12) |
C8 | 0.0686 (17) | 0.0459 (14) | 0.079 (2) | −0.0112 (13) | 0.0176 (14) | 0.0124 (13) |
C9 | 0.0588 (15) | 0.0608 (16) | 0.0639 (18) | 0.0065 (13) | 0.0111 (12) | 0.0240 (14) |
C10 | 0.0568 (15) | 0.0682 (17) | 0.0591 (17) | −0.0006 (13) | −0.0041 (12) | 0.0184 (14) |
C11 | 0.0471 (12) | 0.0447 (12) | 0.0449 (13) | −0.0047 (10) | −0.0014 (9) | 0.0028 (10) |
Geometric parameters (Å, º) top
Cu1—N1 | 2.0471 (19) | C5—H5A | 0.9600 |
Cu1—N2 | 2.0722 (18) | C5—H5B | 0.9600 |
Cu1—Cl2 | 2.2239 (8) | C5—H5C | 0.9600 |
Cu1—Cl1 | 2.2472 (7) | C6—C11 | 1.517 (3) |
N1—C3 | 1.477 (3) | C6—C7 | 1.526 (3) |
N1—C1 | 1.478 (3) | C6—H6 | 0.9800 |
N1—C2 | 1.486 (3) | C7—C8 | 1.524 (4) |
N2—C4 | 1.477 (3) | C7—H7A | 0.9700 |
N2—C5 | 1.490 (3) | C7—H7B | 0.9700 |
N2—C6 | 1.497 (3) | C8—C9 | 1.503 (5) |
C1—H1A | 0.9600 | C8—H8A | 0.9700 |
C1—H1B | 0.9600 | C8—H8B | 0.9700 |
C1—H1C | 0.9600 | C9—C10 | 1.515 (4) |
C2—H2A | 0.9600 | C9—H9A | 0.9700 |
C2—H2B | 0.9600 | C9—H9B | 0.9700 |
C2—H2C | 0.9600 | C10—C11 | 1.514 (4) |
C3—C4 | 1.499 (3) | C10—H10A | 0.9700 |
C3—H3A | 0.9700 | C10—H10B | 0.9700 |
C3—H3B | 0.9700 | C11—H11A | 0.9700 |
C4—H4A | 0.9700 | C11—H11B | 0.9700 |
C4—H4B | 0.9700 | | |
| | | |
N1—Cu1—N2 | 85.31 (8) | N2—C5—H5A | 109.5 |
N1—Cu1—Cl2 | 168.35 (6) | N2—C5—H5B | 109.5 |
N2—Cu1—Cl2 | 92.84 (6) | H5A—C5—H5B | 109.5 |
N1—Cu1—Cl1 | 91.62 (6) | N2—C5—H5C | 109.5 |
N2—Cu1—Cl1 | 167.53 (6) | H5A—C5—H5C | 109.5 |
Cl2—Cu1—Cl1 | 92.54 (3) | H5B—C5—H5C | 109.5 |
C3—N1—C1 | 108.42 (19) | N2—C6—C11 | 110.79 (18) |
C3—N1—C2 | 110.2 (2) | N2—C6—C7 | 114.00 (19) |
C1—N1—C2 | 109.1 (2) | C11—C6—C7 | 110.5 (2) |
C3—N1—Cu1 | 106.12 (14) | N2—C6—H6 | 107.1 |
C1—N1—Cu1 | 113.70 (16) | C11—C6—H6 | 107.1 |
C2—N1—Cu1 | 109.20 (16) | C7—C6—H6 | 107.1 |
C4—N2—C5 | 109.1 (2) | C8—C7—C6 | 110.8 (2) |
C4—N2—C6 | 112.31 (17) | C8—C7—H7A | 109.5 |
C5—N2—C6 | 110.37 (19) | C6—C7—H7A | 109.5 |
C4—N2—Cu1 | 106.99 (14) | C8—C7—H7B | 109.5 |
C5—N2—Cu1 | 107.66 (14) | C6—C7—H7B | 109.5 |
C6—N2—Cu1 | 110.21 (13) | H7A—C7—H7B | 108.1 |
N1—C1—H1A | 109.5 | C9—C8—C7 | 111.2 (2) |
N1—C1—H1B | 109.5 | C9—C8—H8A | 109.4 |
H1A—C1—H1B | 109.5 | C7—C8—H8A | 109.4 |
N1—C1—H1C | 109.5 | C9—C8—H8B | 109.4 |
H1A—C1—H1C | 109.5 | C7—C8—H8B | 109.4 |
H1B—C1—H1C | 109.5 | H8A—C8—H8B | 108.0 |
N1—C2—H2A | 109.5 | C8—C9—C10 | 110.7 (2) |
N1—C2—H2B | 109.5 | C8—C9—H9A | 109.5 |
H2A—C2—H2B | 109.5 | C10—C9—H9A | 109.5 |
N1—C2—H2C | 109.5 | C8—C9—H9B | 109.5 |
H2A—C2—H2C | 109.5 | C10—C9—H9B | 109.5 |
H2B—C2—H2C | 109.5 | H9A—C9—H9B | 108.1 |
N1—C3—C4 | 109.77 (19) | C11—C10—C9 | 110.9 (2) |
N1—C3—H3A | 109.7 | C11—C10—H10A | 109.5 |
C4—C3—H3A | 109.7 | C9—C10—H10A | 109.5 |
N1—C3—H3B | 109.7 | C11—C10—H10B | 109.5 |
C4—C3—H3B | 109.7 | C9—C10—H10B | 109.5 |
H3A—C3—H3B | 108.2 | H10A—C10—H10B | 108.0 |
N2—C4—C3 | 109.90 (18) | C10—C11—C6 | 111.3 (2) |
N2—C4—H4A | 109.7 | C10—C11—H11A | 109.4 |
C3—C4—H4A | 109.7 | C6—C11—H11A | 109.4 |
N2—C4—H4B | 109.7 | C10—C11—H11B | 109.4 |
C3—C4—H4B | 109.7 | C6—C11—H11B | 109.4 |
H4A—C4—H4B | 108.2 | H11A—C11—H11B | 108.0 |
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