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In the title compound, [CuCl(C
10H
22N
2)], the Cu atom is connected to two N atoms of two crystallographically independent piperidine ligands and one Cl atom within a distorted trigonal-planar coordination. The complex molecules are stacked in the direction of the crystallographic
b axis and are connected into chains
via N—H
Cl hydrogen bonding along the crystallographic
c axis.
Supporting information
CCDC reference: 245157
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.089
- Data-to-parameter ratio = 23.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 33.27 su
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: IPDS Program Package (Stoe & Cie, 1998); cell refinement: IPDS Program Package; data reduction: IPDS Program Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: CIFTAB in SHELXTL.
Crystal data top
[CuCl(C10H22N2)] | F(000) = 568 |
Mr = 269.29 | Dx = 1.390 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.355 (2) Å | Cell parameters from 8000 reflections |
b = 6.5407 (4) Å | θ = 10–23° |
c = 9.7669 (11) Å | µ = 1.87 mm−1 |
β = 98.314 (13)° | T = 170 K |
V = 1286.7 (2) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.18 × 0.07 mm |
Data collection top
Stoe IPDS diffractometer | 3062 independent reflections |
Radiation source: fine-focus sealed tube | 2373 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ scans | θmax = 27.9°, θmin = 3.0° |
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 1998) | h = −26→26 |
Tmin = 0.670, Tmax = 0.873 | k = −8→8 |
7942 measured reflections | l = −12→9 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0611P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
3062 reflections | Δρmax = 0.63 e Å−3 |
128 parameters | Δρmin = −0.48 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0148 (17) |
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 | 0.248880 (11) | 0.44348 (3) | 0.75982 (3) | 0.02517 (11) | |
Cl1 | 0.25755 (3) | 0.55842 (7) | 0.53857 (5) | 0.02995 (14) | |
N1 | 0.17893 (8) | 0.5734 (2) | 0.85442 (18) | 0.0216 (3) | |
H1 | 0.2010 | 0.6592 | 0.9219 | 0.026* | |
C1 | 0.14252 (11) | 0.4225 (3) | 0.9284 (2) | 0.0274 (4) | |
H1A | 0.1126 | 0.4947 | 0.9837 | 0.033* | |
H1B | 0.1744 | 0.3408 | 0.9923 | 0.033* | |
C2 | 0.10211 (10) | 0.2819 (3) | 0.8242 (2) | 0.0297 (5) | |
H2A | 0.0772 | 0.1832 | 0.8738 | 0.036* | |
H2B | 0.1324 | 0.2037 | 0.7732 | 0.036* | |
C3 | 0.05357 (11) | 0.4048 (3) | 0.7220 (3) | 0.0320 (5) | |
H3A | 0.0315 | 0.3126 | 0.6491 | 0.038* | |
H3B | 0.0189 | 0.4653 | 0.7710 | 0.038* | |
C4 | 0.08948 (10) | 0.5746 (3) | 0.6555 (2) | 0.0299 (5) | |
H4A | 0.1184 | 0.5134 | 0.5932 | 0.036* | |
H4B | 0.0564 | 0.6625 | 0.5991 | 0.036* | |
C5 | 0.13133 (9) | 0.7043 (3) | 0.7639 (2) | 0.0255 (4) | |
H5A | 0.1560 | 0.8079 | 0.7177 | 0.031* | |
H5B | 0.1021 | 0.7768 | 0.8206 | 0.031* | |
N11 | 0.31952 (8) | 0.2323 (2) | 0.81110 (18) | 0.0220 (3) | |
H11 | 0.3102 | 0.1687 | 0.8913 | 0.026* | |
C11 | 0.32037 (11) | 0.0701 (3) | 0.7051 (2) | 0.0287 (5) | |
H11A | 0.3274 | 0.1341 | 0.6165 | 0.034* | |
H11B | 0.2766 | 0.0014 | 0.6903 | 0.034* | |
C12 | 0.37434 (12) | −0.0900 (3) | 0.7453 (3) | 0.0346 (5) | |
H12A | 0.3640 | −0.1688 | 0.8260 | 0.042* | |
H12B | 0.3753 | −0.1865 | 0.6675 | 0.042* | |
C13 | 0.44217 (11) | 0.0103 (4) | 0.7809 (3) | 0.0353 (5) | |
H13A | 0.4553 | 0.0733 | 0.6968 | 0.042* | |
H13B | 0.4756 | −0.0947 | 0.8149 | 0.042* | |
C14 | 0.44032 (10) | 0.1737 (3) | 0.8918 (2) | 0.0326 (5) | |
H14A | 0.4838 | 0.2441 | 0.9093 | 0.039* | |
H14B | 0.4320 | 0.1086 | 0.9792 | 0.039* | |
C15 | 0.38564 (10) | 0.3296 (3) | 0.8453 (2) | 0.0259 (4) | |
H15A | 0.3840 | 0.4311 | 0.9199 | 0.031* | |
H15B | 0.3965 | 0.4034 | 0.7629 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02099 (15) | 0.02082 (15) | 0.03341 (18) | 0.00391 (9) | 0.00296 (10) | −0.00324 (10) |
Cl1 | 0.0403 (3) | 0.0235 (2) | 0.0271 (3) | 0.0106 (2) | 0.0083 (2) | 0.0035 (2) |
N1 | 0.0231 (8) | 0.0162 (7) | 0.0252 (9) | 0.0016 (6) | 0.0025 (6) | −0.0039 (6) |
C1 | 0.0313 (10) | 0.0264 (10) | 0.0252 (10) | 0.0006 (8) | 0.0059 (8) | 0.0016 (8) |
C2 | 0.0316 (10) | 0.0179 (9) | 0.0392 (13) | −0.0035 (8) | 0.0038 (9) | 0.0030 (9) |
C3 | 0.0263 (10) | 0.0310 (11) | 0.0366 (13) | −0.0045 (8) | −0.0029 (9) | 0.0013 (10) |
C4 | 0.0230 (9) | 0.0301 (11) | 0.0345 (12) | 0.0030 (8) | −0.0033 (8) | 0.0082 (9) |
C5 | 0.0259 (9) | 0.0152 (8) | 0.0357 (12) | 0.0044 (7) | 0.0054 (8) | 0.0009 (8) |
N11 | 0.0233 (8) | 0.0200 (7) | 0.0232 (8) | 0.0036 (6) | 0.0049 (6) | 0.0050 (7) |
C11 | 0.0313 (10) | 0.0220 (10) | 0.0311 (12) | 0.0058 (8) | −0.0007 (9) | −0.0028 (9) |
C12 | 0.0402 (12) | 0.0224 (10) | 0.0409 (14) | 0.0117 (9) | 0.0044 (10) | −0.0015 (9) |
C13 | 0.0300 (11) | 0.0375 (11) | 0.0384 (13) | 0.0146 (9) | 0.0051 (10) | 0.0041 (10) |
C14 | 0.0260 (10) | 0.0367 (11) | 0.0335 (12) | 0.0047 (9) | −0.0010 (8) | 0.0047 (10) |
C15 | 0.0272 (9) | 0.0223 (9) | 0.0279 (10) | 0.0013 (8) | 0.0032 (8) | 0.0036 (8) |
Geometric parameters (Å, º) top
Cu1—N1 | 1.9959 (16) | C5—H5B | 0.9900 |
Cu1—N11 | 2.0045 (15) | N11—C15 | 1.483 (2) |
Cu1—Cl1 | 2.3187 (6) | N11—C11 | 1.484 (3) |
N1—C1 | 1.483 (3) | N11—H11 | 0.9300 |
N1—C5 | 1.485 (2) | C11—C12 | 1.527 (3) |
N1—H1 | 0.9300 | C11—H11A | 0.9900 |
C1—C2 | 1.521 (3) | C11—H11B | 0.9900 |
C1—H1A | 0.9900 | C12—C13 | 1.523 (3) |
C1—H1B | 0.9900 | C12—H12A | 0.9900 |
C2—C3 | 1.528 (3) | C12—H12B | 0.9900 |
C2—H2A | 0.9900 | C13—C14 | 1.526 (3) |
C2—H2B | 0.9900 | C13—H13A | 0.9900 |
C3—C4 | 1.526 (3) | C13—H13B | 0.9900 |
C3—H3A | 0.9900 | C14—C15 | 1.529 (3) |
C3—H3B | 0.9900 | C14—H14A | 0.9900 |
C4—C5 | 1.518 (3) | C14—H14B | 0.9900 |
C4—H4A | 0.9900 | C15—H15A | 0.9900 |
C4—H4B | 0.9900 | C15—H15B | 0.9900 |
C5—H5A | 0.9900 | | |
| | | |
N1—Cu1—N11 | 135.37 (7) | H5A—C5—H5B | 108.1 |
N1—Cu1—Cl1 | 116.68 (5) | C15—N11—C11 | 111.23 (16) |
N11—Cu1—Cl1 | 107.92 (5) | C15—N11—Cu1 | 110.81 (12) |
C1—N1—C5 | 110.16 (15) | C11—N11—Cu1 | 113.49 (12) |
C1—N1—Cu1 | 112.47 (11) | C15—N11—H11 | 107.0 |
C5—N1—Cu1 | 114.66 (13) | C11—N11—H11 | 107.0 |
C1—N1—H1 | 106.3 | Cu1—N11—H11 | 107.0 |
C5—N1—H1 | 106.3 | N11—C11—C12 | 113.05 (17) |
Cu1—N1—H1 | 106.3 | N11—C11—H11A | 109.0 |
N1—C1—C2 | 109.66 (18) | C12—C11—H11A | 109.0 |
N1—C1—H1A | 109.7 | N11—C11—H11B | 109.0 |
C2—C1—H1A | 109.7 | C12—C11—H11B | 109.0 |
N1—C1—H1B | 109.7 | H11A—C11—H11B | 107.8 |
C2—C1—H1B | 109.7 | C13—C12—C11 | 110.97 (18) |
H1A—C1—H1B | 108.2 | C13—C12—H12A | 109.4 |
C1—C2—C3 | 110.81 (17) | C11—C12—H12A | 109.4 |
C1—C2—H2A | 109.5 | C13—C12—H12B | 109.4 |
C3—C2—H2A | 109.5 | C11—C12—H12B | 109.4 |
C1—C2—H2B | 109.5 | H12A—C12—H12B | 108.0 |
C3—C2—H2B | 109.5 | C12—C13—C14 | 110.46 (19) |
H2A—C2—H2B | 108.1 | C12—C13—H13A | 109.6 |
C4—C3—C2 | 110.91 (17) | C14—C13—H13A | 109.6 |
C4—C3—H3A | 109.5 | C12—C13—H13B | 109.6 |
C2—C3—H3A | 109.5 | C14—C13—H13B | 109.6 |
C4—C3—H3B | 109.5 | H13A—C13—H13B | 108.1 |
C2—C3—H3B | 109.5 | C13—C14—C15 | 110.34 (18) |
H3A—C3—H3B | 108.0 | C13—C14—H14A | 109.6 |
C5—C4—C3 | 111.40 (19) | C15—C14—H14A | 109.6 |
C5—C4—H4A | 109.3 | C13—C14—H14B | 109.6 |
C3—C4—H4A | 109.3 | C15—C14—H14B | 109.6 |
C5—C4—H4B | 109.3 | H14A—C14—H14B | 108.1 |
C3—C4—H4B | 109.3 | N11—C15—C14 | 112.24 (16) |
H4A—C4—H4B | 108.0 | N11—C15—H15A | 109.2 |
N1—C5—C4 | 110.20 (15) | C14—C15—H15A | 109.2 |
N1—C5—H5A | 109.6 | N11—C15—H15B | 109.2 |
C4—C5—H5A | 109.6 | C14—C15—H15B | 109.2 |
N1—C5—H5B | 109.6 | H15A—C15—H15B | 107.9 |
C4—C5—H5B | 109.6 | | |
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