Di­chloro­[(6R,7S,8S,14R)-(−)-α-isosparteine-κ²N,N′]­zinc(II)

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 Zn^II ion is highly distorted from tetrahedral, with a dihedral angle between the ZnN₂ and ZnCl₂ planes of 71.58 (6)°.

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

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Computing details

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)

Crystal data

[ZnCl2(C15H26N2)]	Dx = 1.490 Mg m^−3
Mr = 370.65	Melting point > 673 K
Tetragonal, P43212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4nw 2abw	Cell parameters from 60 reflections
a = 8.0474 (7) Å	θ = 3.9–12.4°
c = 25.518 (3) Å	µ = 1.80 mm^−1
V = 1652.6 (3) Å^3	T = 296 K
Z = 4	Prism, colorless
F(000) = 776	0.28 × 0.28 × 0.20 mm

Data collection

Bruker P4 diffractometer	1184 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, FN4	Rint = 0.036
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
2θ/ω scans	h = −9→9
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	k = −9→9
Tmin = 0.597, Tmax = 0.697	l = −30→30
6151 measured reflections	3 standard reflections every 97 reflections
1467 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0202P)^2 + 0.647P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.065	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.18 e Å^−3
1467 reflections	Δρmin = −0.20 e Å^−3
93 parameters	Extinction correction: SHELXTL-Plus, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0014 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 535 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (5)

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
Zn1	0.00093 (4)	0.00093 (4)	0.0000	0.04071 (15)
Cl1	−0.22302 (10)	0.00280 (15)	0.05186 (3)	0.0617 (2)
N1	0.2483 (3)	0.0186 (3)	0.02469 (9)	0.0447 (6)
C2	0.3065 (5)	−0.1444 (4)	0.04513 (15)	0.0651 (12)
H2B	0.4238	−0.1368	0.0537	0.078*
H2C	0.2936	−0.2282	0.0181	0.078*
C3	0.2114 (6)	−0.1965 (5)	0.09309 (14)	0.0732 (12)
H3C	0.2542	−0.3018	0.1057	0.088*
H3D	0.0953	−0.2117	0.0841	0.088*
C4	0.2264 (7)	−0.0664 (5)	0.13609 (14)	0.0815 (15)
H4C	0.1550	−0.0963	0.1652	0.098*
H4D	0.3400	−0.0628	0.1487	0.098*
C5	0.1771 (5)	0.1031 (5)	0.11532 (14)	0.0628 (12)
H5C	0.1973	0.1862	0.1421	0.075*
H5D	0.0591	0.1034	0.1075	0.075*
C6	0.2739 (5)	0.1488 (4)	0.06599 (13)	0.0534 (10)
H6C	0.3921	0.1470	0.0753	0.064*
C7	0.2367 (5)	0.3208 (4)	0.04375 (14)	0.0565 (10)
H7B	0.2551	0.4016	0.0719	0.068*
C15	0.3475 (4)	0.0602 (5)	−0.02302 (14)	0.0557 (10)
H15A	0.3193	−0.0181	−0.0505	0.067*
H15B	0.4644	0.0458	−0.0150	0.067*
C17	0.3600 (5)	0.3600 (5)	0.0000	0.0716 (16)
H17A	0.4721	0.3493	0.0121	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.03894 (17)	0.03894 (17)	0.0442 (2)	−0.0023 (3)	−0.00102 (17)	0.00102 (17)
Cl1	0.0498 (5)	0.0732 (6)	0.0621 (4)	−0.0082 (6)	0.0115 (4)	0.0100 (6)
N1	0.0410 (15)	0.0378 (16)	0.0553 (13)	0.0053 (14)	−0.0098 (13)	−0.0059 (14)
C2	0.072 (3)	0.043 (2)	0.080 (3)	0.010 (2)	−0.033 (2)	−0.010 (2)
C3	0.097 (3)	0.047 (2)	0.076 (2)	0.001 (2)	−0.025 (3)	0.011 (2)
C4	0.118 (4)	0.064 (3)	0.063 (2)	−0.002 (3)	−0.030 (3)	0.002 (2)
C5	0.076 (3)	0.054 (2)	0.059 (2)	−0.006 (2)	−0.013 (2)	−0.0148 (19)
C6	0.046 (2)	0.044 (2)	0.071 (2)	−0.0030 (18)	−0.015 (2)	−0.0157 (18)
C7	0.059 (2)	0.0366 (19)	0.074 (2)	−0.0041 (17)	0.000 (2)	−0.0104 (17)
C15	0.0295 (17)	0.066 (2)	0.072 (2)	0.0073 (17)	−0.0019 (17)	−0.017 (2)
C17	0.055 (2)	0.055 (2)	0.104 (4)	−0.015 (3)	−0.001 (3)	0.001 (3)

Geometric parameters (Å, º)

Zn1—N1	2.093 (2)	C4—H4D	0.970
Zn1—N1^i	2.093 (2)	C5—C6	1.525 (5)
Zn1—Cl1^i	2.2359 (9)	C5—H5C	0.970
Zn1—Cl1	2.2359 (9)	C5—H5D	0.970
N1—C2	1.487 (4)	C6—C7	1.526 (5)
N1—C15	1.494 (4)	C6—H6C	0.980
N1—C6	1.500 (4)	C7—C17	1.527 (4)
C2—C3	1.503 (5)	C7—C15^i	1.531 (5)
C2—H2B	0.970	C7—H7B	0.980
C2—H2C	0.970	C15—C7^i	1.531 (5)
C3—C4	1.521 (5)	C15—H15A	0.970
C3—H3C	0.970	C15—H15B	0.970
C3—H3D	0.970	C17—C7^i	1.527 (4)
C4—C5	1.517 (5)	C17—H17A	0.9571
C4—H4C	0.970
N1—Zn1—N1^i	87.79 (15)	H4C—C4—H4D	108.1
N1—Zn1—Cl1^i	103.09 (8)	C4—C5—C6	111.8 (3)
N1^i—Zn1—Cl1^i	126.02 (7)	C4—C5—H5C	109.3
N1—Zn1—Cl1	126.02 (7)	C6—C5—H5C	109.3
N1^i—Zn1—Cl1	103.09 (8)	C4—C5—H5D	109.3
Cl1^i—Zn1—Cl1	111.17 (6)	C6—C5—H5D	109.3
C2—N1—C15	108.3 (3)	H5C—C5—H5D	107.9
C2—N1—C6	109.0 (2)	N1—C6—C5	110.0 (3)
C15—N1—C6	110.0 (3)	N1—C6—C7	110.2 (3)
C2—N1—Zn1	110.2 (2)	C5—C6—C7	115.2 (3)
C15—N1—Zn1	106.15 (18)	N1—C6—H6C	107.0
C6—N1—Zn1	112.9 (2)	C5—C6—H6C	107.0
N1—C2—C3	111.8 (3)	C7—C6—H6C	107.0
N1—C2—H2B	109.3	C6—C7—C17	109.4 (3)
C3—C2—H2B	109.3	C6—C7—C15^i	116.0 (3)
N1—C2—H2C	109.3	C17—C7—C15^i	108.8 (3)
C3—C2—H2C	109.3	C6—C7—H7B	107.5
H2B—C2—H2C	107.9	C17—C7—H7B	107.5
C2—C3—C4	110.8 (3)	C15^i—C7—H7B	107.5
C2—C3—H3C	109.5	N1—C15—C7^i	114.5 (3)
C4—C3—H3C	109.5	N1—C15—H15A	108.6
C2—C3—H3D	109.5	C7^i—C15—H15A	108.6
C4—C3—H3D	109.5	N1—C15—H15B	108.6
H3C—C3—H3D	108.1	C7^i—C15—H15B	108.6
C5—C4—C3	110.3 (3)	H15A—C15—H15B	107.6
C5—C4—H4C	109.6	C7^i—C17—C7	105.4 (4)
C3—C4—H4C	109.6	C7^i—C17—H17A	111.9
C5—C4—H4D	109.6	C7—C17—H17A	110.9
C3—C4—H4D	109.6
N1^i—Zn1—N1—C2	−176.8 (3)	C15—N1—C6—C5	−178.1 (3)
Cl1^i—Zn1—N1—C2	−50.3 (2)	Zn1—N1—C6—C5	63.4 (3)
Cl1—Zn1—N1—C2	78.5 (2)	C2—N1—C6—C7	172.6 (3)
N1^i—Zn1—N1—C15	−59.72 (18)	C15—N1—C6—C7	53.9 (4)
Cl1^i—Zn1—N1—C15	66.8 (2)	Zn1—N1—C6—C7	−64.6 (3)
Cl1—Zn1—N1—C15	−164.33 (17)	C4—C5—C6—N1	57.2 (4)
N1^i—Zn1—N1—C6	60.94 (19)	C4—C5—C6—C7	−177.6 (3)
Cl1^i—Zn1—N1—C6	−172.53 (19)	N1—C6—C7—C17	−63.5 (4)
Cl1—Zn1—N1—C6	−43.7 (2)	C5—C6—C7—C17	171.4 (3)
C15—N1—C2—C3	−179.4 (3)	N1—C6—C7—C15^i	59.9 (4)
C6—N1—C2—C3	60.8 (4)	C5—C6—C7—C15^i	−65.2 (4)
Zn1—N1—C2—C3	−63.7 (3)	C2—N1—C15—C7^i	−171.0 (3)
N1—C2—C3—C4	−58.0 (4)	C6—N1—C15—C7^i	−51.9 (4)
C2—C3—C4—C5	53.2 (5)	Zn1—N1—C15—C7^i	70.6 (3)
C3—C4—C5—C6	−53.5 (5)	C6—C7—C17—C7^i	66.3 (2)
C2—N1—C6—C5	−59.4 (4)	C15^i—C7—C17—C7^i	−61.3 (2)

Symmetry code: (i) y, x, −z.