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The title compound, [ZnCl2(C15H26N2)], was obtained as a by-product during the synthesis of the corresponding complex of the naturally occurring ligand (6R,7S,8S,14S)-(−)-sparteine, as a result of impurity of the starting material. The mol­ecule lies on a twofold axis. The geometry around the ZnII ion is highly distorted from tetrahedral, with a dihedral angle between the ZnN2 and ZnCl2 planes of 71.58 (6)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022414/cf6282sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022414/cf6282Isup2.hkl
Contains datablock I

CCDC reference: 226644

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.032
  • wR factor = 0.065
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT764_ALERT_4_C Overcomplete CIF Bond list Detected (Rep/Expd) . 1.14 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1467 Count of symmetry unique reflns 932 Completeness (_total/calc) 157.40% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 535 Fraction of Friedel pairs measured 0.574 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

dichloro[(6R,7S,8R,14S)-1,3,4,7,7a,8,9,10,11,13,14,14a-dodecahydro-7,14- methano-2H,6H-dipyrido[1,2 - a;1',2'-e][1,5]diazocine-κ2N,N']zinc(II) top
Crystal data top
[ZnCl2(C15H26N2)]Dx = 1.490 Mg m3
Mr = 370.65Melting point > 673 K
Tetragonal, P43212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4nw 2abwCell parameters from 60 reflections
a = 8.0474 (7) Åθ = 3.9–12.4°
c = 25.518 (3) ŵ = 1.80 mm1
V = 1652.6 (3) Å3T = 296 K
Z = 4Prism, colorless
F(000) = 7760.28 × 0.28 × 0.20 mm
Data collection top
Bruker P4
diffractometer
1184 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, FN4Rint = 0.036
Graphite monochromatorθmax = 25.0°, θmin = 2.7°
2θ/ω scansh = 99
Absorption correction: ψ scan
(XSCANS; Siemens, 1996)
k = 99
Tmin = 0.597, Tmax = 0.697l = 3030
6151 measured reflections3 standard reflections every 97 reflections
1467 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0202P)2 + 0.647P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.065(Δ/σ)max < 0.001
S = 1.11Δρmax = 0.18 e Å3
1467 reflectionsΔρmin = 0.20 e Å3
93 parametersExtinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0014 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 535 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (5)
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
Zn10.00093 (4)0.00093 (4)0.00000.04071 (15)
Cl10.22302 (10)0.00280 (15)0.05186 (3)0.0617 (2)
N10.2483 (3)0.0186 (3)0.02469 (9)0.0447 (6)
C20.3065 (5)0.1444 (4)0.04513 (15)0.0651 (12)
H2B0.42380.13680.05370.078*
H2C0.29360.22820.01810.078*
C30.2114 (6)0.1965 (5)0.09309 (14)0.0732 (12)
H3C0.25420.30180.10570.088*
H3D0.09530.21170.08410.088*
C40.2264 (7)0.0664 (5)0.13609 (14)0.0815 (15)
H4C0.15500.09630.16520.098*
H4D0.34000.06280.14870.098*
C50.1771 (5)0.1031 (5)0.11532 (14)0.0628 (12)
H5C0.19730.18620.14210.075*
H5D0.05910.10340.10750.075*
C60.2739 (5)0.1488 (4)0.06599 (13)0.0534 (10)
H6C0.39210.14700.07530.064*
C70.2367 (5)0.3208 (4)0.04375 (14)0.0565 (10)
H7B0.25510.40160.07190.068*
C150.3475 (4)0.0602 (5)0.02302 (14)0.0557 (10)
H15A0.31930.01810.05050.067*
H15B0.46440.04580.01500.067*
C170.3600 (5)0.3600 (5)0.00000.0716 (16)
H17A0.47210.34930.01210.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03894 (17)0.03894 (17)0.0442 (2)0.0023 (3)0.00102 (17)0.00102 (17)
Cl10.0498 (5)0.0732 (6)0.0621 (4)0.0082 (6)0.0115 (4)0.0100 (6)
N10.0410 (15)0.0378 (16)0.0553 (13)0.0053 (14)0.0098 (13)0.0059 (14)
C20.072 (3)0.043 (2)0.080 (3)0.010 (2)0.033 (2)0.010 (2)
C30.097 (3)0.047 (2)0.076 (2)0.001 (2)0.025 (3)0.011 (2)
C40.118 (4)0.064 (3)0.063 (2)0.002 (3)0.030 (3)0.002 (2)
C50.076 (3)0.054 (2)0.059 (2)0.006 (2)0.013 (2)0.0148 (19)
C60.046 (2)0.044 (2)0.071 (2)0.0030 (18)0.015 (2)0.0157 (18)
C70.059 (2)0.0366 (19)0.074 (2)0.0041 (17)0.000 (2)0.0104 (17)
C150.0295 (17)0.066 (2)0.072 (2)0.0073 (17)0.0019 (17)0.017 (2)
C170.055 (2)0.055 (2)0.104 (4)0.015 (3)0.001 (3)0.001 (3)
Geometric parameters (Å, º) top
Zn1—N12.093 (2)C4—H4D0.970
Zn1—N1i2.093 (2)C5—C61.525 (5)
Zn1—Cl1i2.2359 (9)C5—H5C0.970
Zn1—Cl12.2359 (9)C5—H5D0.970
N1—C21.487 (4)C6—C71.526 (5)
N1—C151.494 (4)C6—H6C0.980
N1—C61.500 (4)C7—C171.527 (4)
C2—C31.503 (5)C7—C15i1.531 (5)
C2—H2B0.970C7—H7B0.980
C2—H2C0.970C15—C7i1.531 (5)
C3—C41.521 (5)C15—H15A0.970
C3—H3C0.970C15—H15B0.970
C3—H3D0.970C17—C7i1.527 (4)
C4—C51.517 (5)C17—H17A0.9571
C4—H4C0.970
N1—Zn1—N1i87.79 (15)H4C—C4—H4D108.1
N1—Zn1—Cl1i103.09 (8)C4—C5—C6111.8 (3)
N1i—Zn1—Cl1i126.02 (7)C4—C5—H5C109.3
N1—Zn1—Cl1126.02 (7)C6—C5—H5C109.3
N1i—Zn1—Cl1103.09 (8)C4—C5—H5D109.3
Cl1i—Zn1—Cl1111.17 (6)C6—C5—H5D109.3
C2—N1—C15108.3 (3)H5C—C5—H5D107.9
C2—N1—C6109.0 (2)N1—C6—C5110.0 (3)
C15—N1—C6110.0 (3)N1—C6—C7110.2 (3)
C2—N1—Zn1110.2 (2)C5—C6—C7115.2 (3)
C15—N1—Zn1106.15 (18)N1—C6—H6C107.0
C6—N1—Zn1112.9 (2)C5—C6—H6C107.0
N1—C2—C3111.8 (3)C7—C6—H6C107.0
N1—C2—H2B109.3C6—C7—C17109.4 (3)
C3—C2—H2B109.3C6—C7—C15i116.0 (3)
N1—C2—H2C109.3C17—C7—C15i108.8 (3)
C3—C2—H2C109.3C6—C7—H7B107.5
H2B—C2—H2C107.9C17—C7—H7B107.5
C2—C3—C4110.8 (3)C15i—C7—H7B107.5
C2—C3—H3C109.5N1—C15—C7i114.5 (3)
C4—C3—H3C109.5N1—C15—H15A108.6
C2—C3—H3D109.5C7i—C15—H15A108.6
C4—C3—H3D109.5N1—C15—H15B108.6
H3C—C3—H3D108.1C7i—C15—H15B108.6
C5—C4—C3110.3 (3)H15A—C15—H15B107.6
C5—C4—H4C109.6C7i—C17—C7105.4 (4)
C3—C4—H4C109.6C7i—C17—H17A111.9
C5—C4—H4D109.6C7—C17—H17A110.9
C3—C4—H4D109.6
N1i—Zn1—N1—C2176.8 (3)C15—N1—C6—C5178.1 (3)
Cl1i—Zn1—N1—C250.3 (2)Zn1—N1—C6—C563.4 (3)
Cl1—Zn1—N1—C278.5 (2)C2—N1—C6—C7172.6 (3)
N1i—Zn1—N1—C1559.72 (18)C15—N1—C6—C753.9 (4)
Cl1i—Zn1—N1—C1566.8 (2)Zn1—N1—C6—C764.6 (3)
Cl1—Zn1—N1—C15164.33 (17)C4—C5—C6—N157.2 (4)
N1i—Zn1—N1—C660.94 (19)C4—C5—C6—C7177.6 (3)
Cl1i—Zn1—N1—C6172.53 (19)N1—C6—C7—C1763.5 (4)
Cl1—Zn1—N1—C643.7 (2)C5—C6—C7—C17171.4 (3)
C15—N1—C2—C3179.4 (3)N1—C6—C7—C15i59.9 (4)
C6—N1—C2—C360.8 (4)C5—C6—C7—C15i65.2 (4)
Zn1—N1—C2—C363.7 (3)C2—N1—C15—C7i171.0 (3)
N1—C2—C3—C458.0 (4)C6—N1—C15—C7i51.9 (4)
C2—C3—C4—C553.2 (5)Zn1—N1—C15—C7i70.6 (3)
C3—C4—C5—C653.5 (5)C6—C7—C17—C7i66.3 (2)
C2—N1—C6—C559.4 (4)C15i—C7—C17—C7i61.3 (2)
Symmetry code: (i) y, x, z.
 

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