Chloro­bis­(piperidine-κN)copper(I)

In the title compound, [CuCl(C₁₀H₂₂N₂)], 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.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](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

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Computing details

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.

(I)

Crystal data

[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) Å^3	Block, colourless
Z = 4	0.30 × 0.18 × 0.07 mm

Data collection

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

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)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0611P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0148 (17)

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	0.248880 (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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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