Di-μ-cyano-1:2κ²C:N;2:3κ²N:C-dicyano-1κC,3κC-(5,7,7,12,14,14-hexa­methyl-1,4,8,11-tetra­azacyl­otetra­decane-2κ⁴N)nickel(II)disilver(I)

The title compound, [Ag₂Ni(CN)₄(C₁₅H₃₆N₃)], has been pre­pared by the reaction of teta (5,7,7,12,14,14-hexa­methyl-1,4,8,11-tetra­azacyl­otetra­deca­ne), K[Ag(CN)₂] and Ni(ClO₄)₂. The Ni atom, lying on a centre of symmetry, is octa­hedrally coordinated by four teta N atoms and two cyano N atoms.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.028
• wR factor = 0.077
• Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C1      ..      14.74 su

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ag1    -   C1      ..       8.55 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4     ...          ?
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            C2  -AG1 -C1  -N1    -18.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N2  -NI1 -N2  -C2    -73.00 12.00   5.775   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N3  -NI1 -N3  -C7      8.00  0.00   5.775   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14
            N3  -NI1 -N3  -C6     14.00  0.00   5.775   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            N4  -NI1 -N4  -C9    108.00 13.00   5.775   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         22
            N4  -NI1 -N4  -C8   -124.00 13.00   5.775   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         27
            NI1 -N2  -C2  -AG1   -10.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         28
            C1  -AG1 -C2  -N2   -161.00  4.00   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  15 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
  10 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

di-µ-cyano-1:2κ²C:N;2:3κ²N:C-dicyano-1κC,3κC-(5,7,7,12,14,14- hexamethyl-1,4,8,11-tetraazacylotetradecane-2κ⁴N)nickel(II)disilver(I)

Crystal data

[Ag2Ni(CN)4(C15H36N3)]	Dx = 1.762 Mg m^−3
Mr = 663.02	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3610 reflections
a = 16.435 (2) Å	θ = 2.9–26.0°
b = 8.6228 (13) Å	µ = 2.32 mm^−1
c = 17.634 (3) Å	T = 294 K
V = 2498.9 (6) Å^3	Prism, pale purple
Z = 4	0.22 × 0.16 × 0.14 mm
F(000) = 1336

Data collection

Bruker SMART CCD area-detector diffractometer	2972 independent reflections
Radiation source: fine-focus sealed tube	2229 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 27.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
Tmin = 0.629, Tmax = 0.737	k = −11→11
15725 measured reflections	l = −17→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.035P)^2 + 2.1646P] where P = (Fo^2 + 2Fc^2)/3
2972 reflections	(Δ/σ)max = 0.004
154 parameters	Δρmax = 0.93 e Å^−3
13 restraints	Δρmin = −0.51 e Å^−3

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
Ag1	1.189949 (16)	0.66343 (3)	0.176685 (16)	0.04626 (11)
Ni1	1.0000	1.0000	0.0000	0.02692 (13)
N1	1.3017 (2)	0.4252 (5)	0.2628 (2)	0.0689 (10)
C1	1.2674 (2)	0.5071 (4)	0.23664 (18)	0.0349 (7)
N2	1.06782 (16)	0.8265 (3)	0.05836 (15)	0.0362 (6)
N3	0.98820 (15)	1.1025 (3)	0.10780 (14)	0.0321 (6)
H3	1.018 (2)	1.029 (4)	0.1348 (19)	0.037 (9)*
N4	0.88974 (16)	0.8933 (3)	0.02479 (15)	0.0321 (5)
H4	0.852 (2)	0.948 (4)	0.0044 (17)	0.027 (8)*
C2	1.1102 (2)	0.7633 (4)	0.09948 (18)	0.0385 (7)
C3	1.1087 (2)	1.2683 (4)	0.09019 (19)	0.0417 (8)
H3A	1.1344	1.3623	0.1087	0.050*
H3B	1.1403	1.1818	0.1095	0.050*
C4	1.0337 (3)	1.2741 (5)	0.21299 (19)	0.0573 (10)
H4A	0.9810	1.2742	0.2365	0.086*
H4B	1.0613	1.3694	0.2246	0.086*
H4C	1.0649	1.1883	0.2318	0.086*
C5	0.9689 (2)	1.3901 (4)	0.0986 (2)	0.0475 (9)
H5A	0.9554	1.3733	0.0463	0.071*
H5B	0.9968	1.4874	0.1038	0.071*
H5C	0.9199	1.3921	0.1283	0.071*
C6	1.02382 (19)	1.2590 (4)	0.12652 (18)	0.0373 (7)
C7	0.9026 (2)	1.0766 (4)	0.12970 (19)	0.0422 (8)
H7A	0.8679	1.1513	0.1043	0.051*
H7B	0.8964	1.0903	0.1840	0.051*
C8	0.8780 (2)	0.9142 (4)	0.10764 (18)	0.0427 (8)
H8A	0.9108	0.8394	0.1351	0.051*
H8B	0.8213	0.8969	0.1206	0.051*
C9	0.88291 (19)	0.7322 (4)	−0.00359 (18)	0.0355 (7)
H9	0.9281	0.6721	0.0176	0.043*
C10	0.8034 (2)	0.6535 (5)	0.0197 (3)	0.0562 (10)
H10A	0.7994	0.6521	0.0740	0.084*
H10B	0.8027	0.5491	0.0008	0.084*
H10C	0.7583	0.7099	−0.0011	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.03871 (16)	0.05618 (18)	0.04390 (17)	0.00670 (12)	−0.00599 (12)	0.01447 (12)
Ni1	0.0252 (3)	0.0334 (3)	0.0221 (2)	0.0012 (2)	−0.0003 (2)	0.0027 (2)
N1	0.065 (2)	0.084 (3)	0.058 (2)	−0.002 (2)	0.0038 (18)	−0.012 (2)
C1	0.0385 (17)	0.0370 (16)	0.0292 (16)	−0.0017 (14)	0.0085 (13)	−0.0017 (14)
N2	0.0354 (14)	0.0409 (14)	0.0324 (14)	0.0018 (12)	−0.0036 (12)	0.0031 (12)
N3	0.0322 (13)	0.0369 (14)	0.0274 (13)	0.0028 (11)	−0.0014 (11)	0.0023 (11)
N4	0.0282 (13)	0.0394 (14)	0.0288 (13)	0.0010 (11)	−0.0010 (11)	0.0044 (12)
C2	0.0401 (17)	0.0389 (18)	0.0364 (17)	0.0022 (15)	−0.0047 (15)	0.0031 (15)
C3	0.0386 (18)	0.0454 (19)	0.0412 (19)	−0.0050 (15)	−0.0078 (14)	−0.0048 (15)
C4	0.072 (3)	0.066 (3)	0.034 (2)	−0.003 (2)	−0.0048 (19)	−0.0119 (19)
C5	0.052 (2)	0.0416 (19)	0.049 (2)	0.0075 (17)	−0.0012 (17)	−0.0034 (17)
C6	0.0435 (18)	0.0397 (18)	0.0286 (16)	−0.0021 (14)	−0.0047 (14)	−0.0057 (14)
C7	0.0397 (18)	0.051 (2)	0.0357 (18)	0.0004 (16)	0.0110 (14)	−0.0045 (16)
C8	0.0416 (18)	0.055 (2)	0.0317 (17)	−0.0061 (16)	0.0122 (15)	0.0026 (16)
C9	0.0323 (16)	0.0376 (16)	0.0366 (16)	−0.0048 (14)	−0.0020 (13)	0.0019 (14)
C10	0.045 (2)	0.060 (2)	0.064 (3)	−0.0206 (18)	0.0052 (18)	0.001 (2)

Geometric parameters (Å, º)

Ag1—C2	2.077 (3)	C4—C6	1.539 (4)
Ag1—C1	2.134 (4)	C4—H4A	0.9600
Ni1—N4	2.079 (3)	C4—H4B	0.9600
Ni1—N4^i	2.079 (3)	C4—H4C	0.9600
Ni1—N3^i	2.105 (3)	C5—C6	1.528 (5)
Ni1—N3	2.105 (3)	C5—H5A	0.9600
Ni1—N2^i	2.131 (3)	C5—H5B	0.9600
Ni1—N2	2.131 (3)	C5—H5C	0.9600
N1—C1	1.014 (4)	C7—C8	1.509 (5)
N2—C2	1.144 (4)	C7—H7A	0.9700
N3—C7	1.476 (4)	C7—H7B	0.9700
N3—C6	1.508 (4)	C8—H8A	0.9700
N3—H3	0.94 (3)	C8—H8B	0.9700
N4—C9	1.480 (4)	C9—C10	1.528 (4)
N4—C8	1.485 (4)	C9—C3^i	1.533 (4)
N4—H4	0.85 (3)	C9—H9	0.9800
C3—C9^i	1.533 (4)	C10—H10A	0.9600
C3—C6	1.538 (5)	C10—H10B	0.9600
C3—H3A	0.9700	C10—H10C	0.9600
C3—H3B	0.9700
C2—Ag1—C1	164.36 (13)	C6—C4—H4C	109.5
N4—Ni1—N4^i	180.0	H4A—C4—H4C	109.5
N4—Ni1—N3^i	94.84 (10)	H4B—C4—H4C	109.5
N4^i—Ni1—N3^i	85.16 (10)	C6—C5—H5A	109.5
N4—Ni1—N3	85.16 (10)	C6—C5—H5B	109.5
N4^i—Ni1—N3	94.84 (10)	H5A—C5—H5B	109.5
N3^i—Ni1—N3	180.0	C6—C5—H5C	109.5
N4—Ni1—N2^i	87.50 (10)	H5A—C5—H5C	109.5
N4^i—Ni1—N2^i	92.50 (10)	H5B—C5—H5C	109.5
N3^i—Ni1—N2^i	84.65 (10)	N3—C6—C5	111.3 (3)
N3—Ni1—N2^i	95.35 (10)	N3—C6—C3	107.9 (3)
N4—Ni1—N2	92.50 (10)	C5—C6—C3	111.3 (3)
N4^i—Ni1—N2	87.50 (10)	N3—C6—C4	109.5 (3)
N3^i—Ni1—N2	95.35 (10)	C5—C6—C4	108.6 (3)
N3—Ni1—N2	84.65 (10)	C3—C6—C4	108.2 (3)
N2^i—Ni1—N2	180.0	N3—C7—C8	109.2 (3)
N1—C1—Ag1	175.1 (4)	N3—C7—H7A	109.8
C2—N2—Ni1	163.6 (3)	C8—C7—H7A	109.8
C7—N3—C6	116.6 (3)	N3—C7—H7B	109.8
C7—N3—Ni1	105.12 (19)	C8—C7—H7B	109.8
C6—N3—Ni1	122.52 (19)	H7A—C7—H7B	108.3
C7—N3—H3	106 (2)	N4—C8—C7	109.3 (3)
C6—N3—H3	107 (2)	N4—C8—H8A	109.8
Ni1—N3—H3	97 (2)	C7—C8—H8A	109.8
C9—N4—C8	115.9 (3)	N4—C8—H8B	109.8
C9—N4—Ni1	114.22 (19)	C7—C8—H8B	109.8
C8—N4—Ni1	105.48 (19)	H8A—C8—H8B	108.3
C9—N4—H4	109 (2)	N4—C9—C10	113.0 (3)
C8—N4—H4	105 (2)	N4—C9—C3^i	109.5 (3)
Ni1—N4—H4	107 (2)	C10—C9—C3^i	110.1 (3)
N2—C2—Ag1	176.0 (3)	N4—C9—H9	108.1
C9^i—C3—C6	119.7 (3)	C10—C9—H9	108.1
C9^i—C3—H3A	107.4	C3^i—C9—H9	108.1
C6—C3—H3A	107.4	C9—C10—H10A	109.5
C9^i—C3—H3B	107.4	C9—C10—H10B	109.5
C6—C3—H3B	107.4	H10A—C10—H10B	109.5
H3A—C3—H3B	106.9	C9—C10—H10C	109.5
C6—C4—H4A	109.5	H10A—C10—H10C	109.5
C6—C4—H4B	109.5	H10B—C10—H10C	109.5
H4A—C4—H4B	109.5
C2—Ag1—C1—N1	−18 (4)	N3—Ni1—N4—C8	−14.7 (2)
N4—Ni1—N2—C2	−120.9 (10)	N2^i—Ni1—N4—C8	−110.3 (2)
N4^i—Ni1—N2—C2	59.1 (10)	N2—Ni1—N4—C8	69.7 (2)
N3^i—Ni1—N2—C2	144.0 (10)	Ni1—N2—C2—Ag1	−10 (5)
N3—Ni1—N2—C2	−36.0 (10)	C1—Ag1—C2—N2	−161 (4)
N2^i—Ni1—N2—C2	−73 (12)	C7—N3—C6—C5	−50.5 (4)
N4—Ni1—N3—C7	−14.6 (2)	Ni1—N3—C6—C5	81.2 (3)
N4^i—Ni1—N3—C7	165.4 (2)	C7—N3—C6—C3	−172.9 (3)
N3^i—Ni1—N3—C7	−83 (44)	Ni1—N3—C6—C3	−41.2 (3)
N2^i—Ni1—N3—C7	72.4 (2)	C7—N3—C6—C4	69.5 (4)
N2—Ni1—N3—C7	−107.6 (2)	Ni1—N3—C6—C4	−158.8 (2)
N4—Ni1—N3—C6	−150.9 (2)	C9^i—C3—C6—N3	65.8 (4)
N4^i—Ni1—N3—C6	29.1 (2)	C9^i—C3—C6—C5	−56.6 (4)
N3^i—Ni1—N3—C6	141 (44)	C9^i—C3—C6—C4	−175.8 (3)
N2^i—Ni1—N3—C6	−63.9 (2)	C6—N3—C7—C8	−179.2 (3)
N2—Ni1—N3—C6	116.1 (2)	Ni1—N3—C7—C8	41.5 (3)
N4^i—Ni1—N4—C9	108 (13)	C9—N4—C8—C7	169.1 (3)
N3^i—Ni1—N4—C9	36.9 (2)	Ni1—N4—C8—C7	41.7 (3)
N3—Ni1—N4—C9	−143.1 (2)	N3—C7—C8—N4	−58.0 (4)
N2^i—Ni1—N4—C9	121.3 (2)	C8—N4—C9—C10	53.5 (4)
N2—Ni1—N4—C9	−58.7 (2)	Ni1—N4—C9—C10	176.4 (2)
N4^i—Ni1—N4—C8	−124 (13)	C8—N4—C9—C3^i	176.5 (3)
N3^i—Ni1—N4—C8	165.3 (2)	Ni1—N4—C9—C3^i	−60.6 (3)

Symmetry code: (i) −x+2, −y+2, −z.