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Acta Cryst. (2007). C63, m144-m146
https://doi.org/10.1107/S0108270107008736
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Chlorido­bis[(2-oxoazocan-1-yl)methyl]­germanium(IV) trifluoro­methane­sulfonate

E. A. Komissarov, A. A. Korlyukov, E. P. Kramarova, S. Yu. Bylikin, V. V. Negrebetsky and Y. I. Baukov
In the title compound, [Ge(C8H14NO)2Cl]CF3SO3, which is the first complex containing an eight-membered lactam (enantho­lactam) as ligand, the coordination polyhedron of the GeIV atom is inter­mediate between trigonal-bipyramidal and square-pyramidal. Quantum chemical calculations of the crystal structure indicate the absence of additional coordination bonding between the GeIV atom and the trifluoro­methane­sulfonate anion.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107008736/sk3085sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107008736/sk3085Isup2.hkl
Contains datablock I

CCDC reference: 645510

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Chlorobis[(2-oxoazocan-1-yl)methyl]germanium(IV) trifluoromethanesulfonate top
Crystal data top
[Ge(C8H14NO)2Cl](CF3SO3)F(000) = 1104.0
Mr = 537.54Dx = 1.655 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9806 reflections
a = 14.3288 (5) Åθ = 2.6–31.4°
b = 12.0353 (4) ŵ = 1.70 mm−1
c = 13.1364 (5) ÅT = 100 K
β = 108.131 (1)°Prism, colourless
V = 2152.91 (13) Å30.05 × 0.05 × 0.04 mm
Z = 4
Data collection top
Bruker SMART APEXII area-detector
diffractometer		7284 independent reflections
Radiation source: fine-focus sealed tube5148 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
ω scansθmax = 31.7°, θmin = 1.5°
Absorption correction: multi-scan
(APEX2; Bruker, 2005)		h = −21→21
Tmin = 0.849, Tmax = 0.942k = −17→17
51328 measured reflectionsl = −19→19
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0228P)2]
where P = (Fo2 + 2Fc2)/3
7284 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.50 e Å−3
0 restraintsΔρmin = −0.49 e Å−3
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
Ge10.249433 (12)0.407024 (14)0.498536 (13)0.01104 (4)
Cl10.24478 (3)0.58500 (3)0.47204 (3)0.01666 (8)
O10.10708 (7)0.40111 (9)0.48880 (8)0.0139 (2)
N10.09815 (9)0.33790 (10)0.32506 (10)0.0117 (3)
C10.20536 (11)0.33234 (13)0.36084 (12)0.0128 (3)
H1A0.23200.36990.30880.015*
H1B0.22760.25400.36810.015*
C20.05455 (11)0.37077 (13)0.39538 (13)0.0122 (3)
C3−0.05485 (11)0.37438 (13)0.37075 (13)0.0159 (3)
H3A−0.08480.40000.29610.019*
H3B−0.07150.42930.41850.019*
C4−0.09969 (12)0.26150 (14)0.38446 (14)0.0188 (3)
H4A−0.05890.22840.45280.023*
H4B−0.16580.27490.39090.023*
C5−0.10945 (12)0.17648 (14)0.29540 (14)0.0195 (4)
H5A−0.14130.21310.22570.023*
H5B−0.15370.11640.30360.023*
C6−0.01309 (12)0.12391 (14)0.29179 (14)0.0189 (4)
H6A0.03580.13070.36380.023*
H6B−0.02470.04360.27660.023*
C70.03156 (12)0.17257 (14)0.21012 (13)0.0177 (3)
H7A−0.01100.15270.13730.021*
H7B0.09650.13770.22070.021*
C80.04459 (11)0.29850 (13)0.21636 (12)0.0152 (3)
H8A0.08070.32170.16680.018*
H8B−0.02090.33420.19240.018*
O1'0.39065 (7)0.39322 (9)0.51198 (8)0.0129 (2)
N1'0.40082 (9)0.39501 (11)0.68626 (10)0.0126 (3)
C1'0.29425 (11)0.38593 (13)0.65301 (12)0.0138 (3)
H1'A0.26600.44350.68860.017*
H1'B0.27430.31190.67180.017*
C2'0.44402 (11)0.39279 (12)0.61022 (12)0.0118 (3)
C3'0.45573 (12)0.40059 (14)0.80138 (12)0.0180 (3)
H3'A0.42100.45120.83690.022*
H3'B0.52160.43230.81040.022*
C4'0.46757 (13)0.28794 (15)0.85597 (13)0.0219 (4)
H4'A0.40220.26210.85670.026*
H4'B0.50910.29700.93140.026*
C5'0.51285 (12)0.19844 (14)0.80427 (14)0.0218 (4)
H5'A0.46360.17610.73600.026*
H5'B0.52650.13260.85180.026*
C6'0.60761 (12)0.23022 (14)0.78086 (13)0.0188 (3)
H6'A0.64060.28970.83140.023*
H6'B0.65180.16490.79580.023*
C7'0.59566 (12)0.27015 (14)0.66681 (13)0.0178 (3)
H7'A0.55290.21630.61650.021*
H7'B0.66100.26710.65600.021*
C8'0.55306 (11)0.38740 (13)0.63469 (13)0.0154 (3)
H8'A0.58400.43970.69380.018*
H8'B0.57030.41210.57090.018*
S1T0.26777 (3)0.08849 (4)0.56382 (3)0.01803 (9)
O1T0.17860 (10)0.15214 (12)0.53436 (11)0.0379 (4)
O2T0.34809 (11)0.14487 (14)0.54412 (11)0.0451 (4)
O3T0.29000 (9)0.03138 (10)0.66473 (9)0.0239 (3)
C1T0.24150 (14)−0.02381 (15)0.46581 (15)0.0253 (4)
F1T0.31791 (12)−0.09024 (12)0.48221 (10)0.0673 (5)
F2T0.16502 (11)−0.08255 (11)0.46839 (10)0.0586 (4)
F3T0.22100 (8)0.01551 (9)0.36587 (8)0.0302 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ge10.00931 (7)0.01420 (8)0.00973 (8)−0.00009 (7)0.00313 (5)−0.00091 (7)
Cl10.01610 (18)0.01520 (19)0.01912 (19)0.00030 (15)0.00610 (15)0.00118 (15)
O10.0116 (5)0.0169 (6)0.0139 (6)−0.0013 (4)0.0049 (4)−0.0039 (5)
N10.0111 (6)0.0123 (7)0.0116 (6)−0.0004 (5)0.0033 (5)−0.0006 (5)
C10.0115 (7)0.0158 (8)0.0118 (7)−0.0005 (6)0.0046 (6)−0.0014 (6)
C20.0131 (7)0.0086 (7)0.0148 (8)0.0002 (6)0.0043 (6)0.0005 (6)
C30.0111 (7)0.0187 (8)0.0176 (8)0.0015 (6)0.0039 (6)−0.0034 (6)
C40.0153 (8)0.0228 (9)0.0211 (9)−0.0054 (7)0.0098 (7)−0.0053 (7)
C50.0180 (8)0.0208 (9)0.0194 (9)−0.0076 (7)0.0053 (7)−0.0058 (7)
C60.0218 (9)0.0144 (8)0.0202 (9)−0.0028 (6)0.0061 (7)−0.0031 (6)
C70.0169 (8)0.0212 (9)0.0146 (8)−0.0009 (7)0.0041 (6)−0.0065 (7)
C80.0131 (7)0.0214 (9)0.0097 (8)−0.0003 (6)0.0017 (6)−0.0011 (6)
O1'0.0114 (5)0.0169 (6)0.0106 (5)0.0003 (4)0.0037 (4)0.0008 (4)
N1'0.0105 (6)0.0160 (7)0.0105 (6)−0.0009 (5)0.0023 (5)−0.0005 (5)
C1'0.0116 (7)0.0192 (9)0.0121 (8)−0.0004 (6)0.0057 (6)−0.0012 (6)
C2'0.0124 (7)0.0093 (7)0.0137 (8)−0.0002 (6)0.0041 (6)0.0009 (6)
C3'0.0152 (8)0.0269 (9)0.0105 (8)−0.0005 (7)0.0021 (6)−0.0034 (7)
C4'0.0186 (8)0.0346 (11)0.0119 (8)−0.0027 (7)0.0041 (6)0.0049 (7)
C5'0.0206 (9)0.0229 (9)0.0189 (9)−0.0029 (7)0.0015 (7)0.0072 (7)
C6'0.0179 (8)0.0188 (9)0.0168 (8)0.0017 (7)0.0009 (6)0.0019 (7)
C7'0.0141 (8)0.0224 (9)0.0161 (8)0.0038 (7)0.0035 (6)0.0003 (7)
C8'0.0117 (7)0.0203 (9)0.0144 (8)−0.0001 (6)0.0044 (6)0.0035 (6)
S1T0.0204 (2)0.0180 (2)0.01351 (19)−0.00220 (17)0.00209 (15)0.00030 (16)
O1T0.0439 (9)0.0404 (9)0.0229 (7)0.0241 (7)0.0010 (6)−0.0037 (6)
O2T0.0401 (9)0.0634 (11)0.0283 (8)−0.0318 (8)0.0052 (7)0.0052 (7)
O3T0.0301 (7)0.0267 (7)0.0130 (6)0.0003 (5)0.0041 (5)0.0034 (5)
C1T0.0352 (11)0.0219 (10)0.0165 (9)0.0047 (8)0.0048 (8)0.0012 (7)
F1T0.0935 (12)0.0650 (10)0.0320 (8)0.0602 (9)0.0030 (7)−0.0065 (7)
F2T0.0879 (11)0.0500 (9)0.0336 (8)−0.0496 (8)0.0125 (7)−0.0074 (6)
F3T0.0393 (7)0.0378 (7)0.0116 (5)0.0057 (5)0.0052 (5)0.0010 (5)
Geometric parameters (Å, º) top
Ge1—C11.9410 (15)N1'—C2'1.3291 (19)
Ge1—C1'1.9452 (15)N1'—C1'1.4558 (19)
Ge1—O1'1.9826 (10)N1'—C3'1.4731 (19)
Ge1—O12.0048 (10)C1'—H1'A0.9900
Ge1—Cl12.1678 (4)C1'—H1'B0.9900
O1—C21.2771 (18)C2'—C8'1.495 (2)
N1—C21.3264 (19)C3'—C4'1.518 (2)
N1—C11.4615 (18)C3'—H3'A0.9900
N1—C81.4733 (19)C3'—H3'B0.9900
C1—H1A0.9900C4'—C5'1.522 (2)
C1—H1B0.9900C4'—H4'A0.9900
C2—C31.499 (2)C4'—H4'B0.9900
C3—C41.537 (2)C5'—C6'1.531 (2)
C3—H3A0.9900C5'—H5'A0.9900
C3—H3B0.9900C5'—H5'B0.9900
C4—C51.528 (2)C6'—C7'1.531 (2)
C4—H4A0.9900C6'—H6'A0.9900
C4—H4B0.9900C6'—H6'B0.9900
C5—C61.533 (2)C7'—C8'1.543 (2)
C5—H5A0.9900C7'—H7'A0.9900
C5—H5B0.9900C7'—H7'B0.9900
C6—C71.527 (2)C8'—H8'A0.9900
C6—H6A0.9900C8'—H8'B0.9900
C6—H6B0.9900S1T—O2T1.4273 (14)
C7—C81.526 (2)S1T—O1T1.4356 (13)
C7—H7A0.9900S1T—O3T1.4383 (12)
C7—H7B0.9900S1T—C1T1.8233 (19)
C8—H8A0.9900C1T—F2T1.313 (2)
C8—H8B0.9900C1T—F1T1.318 (2)
O1'—C2'1.2792 (18)C1T—F3T1.339 (2)
C1—Ge1—C1'144.86 (7)C2'—N1'—C1'117.61 (12)
C1—Ge1—O1'94.09 (5)C2'—N1'—C3'123.19 (13)
C1'—Ge1—O1'84.24 (5)C1'—N1'—C3'119.12 (12)
C1—Ge1—O183.95 (5)N1'—C1'—Ge1106.15 (10)
C1'—Ge1—O193.49 (5)N1'—C1'—H1'A110.5
O1'—Ge1—O1173.02 (4)Ge1—C1'—H1'A110.5
C1—Ge1—Cl1108.85 (5)N1'—C1'—H1'B110.5
C1'—Ge1—Cl1106.27 (5)Ge1—C1'—H1'B110.5
O1'—Ge1—Cl194.40 (3)H1'A—C1'—H1'B108.7
O1—Ge1—Cl192.58 (3)O1'—C2'—N1'119.08 (13)
C2—O1—Ge1110.80 (9)O1'—C2'—C8'118.27 (13)
C2—N1—C1117.73 (13)N1'—C2'—C8'122.63 (14)
C2—N1—C8123.70 (13)N1'—C3'—C4'112.93 (13)
C1—N1—C8118.39 (12)N1'—C3'—H3'A109.0
N1—C1—Ge1106.45 (9)C4'—C3'—H3'A109.0
N1—C1—H1A110.4N1'—C3'—H3'B109.0
Ge1—C1—H1A110.4C4'—C3'—H3'B109.0
N1—C1—H1B110.4H3'A—C3'—H3'B107.8
Ge1—C1—H1B110.4C3'—C4'—C5'114.94 (14)
H1A—C1—H1B108.6C3'—C4'—H4'A108.5
O1—C2—N1119.35 (14)C5'—C4'—H4'A108.5
O1—C2—C3117.59 (13)C3'—C4'—H4'B108.5
N1—C2—C3123.07 (14)C5'—C4'—H4'B108.5
C2—C3—C4113.34 (13)H4'A—C4'—H4'B107.5
C2—C3—H3A108.9C4'—C5'—C6'116.14 (14)
C4—C3—H3A108.9C4'—C5'—H5'A108.3
C2—C3—H3B108.9C6'—C5'—H5'A108.3
C4—C3—H3B108.9C4'—C5'—H5'B108.3
H3A—C3—H3B107.7C6'—C5'—H5'B108.3
C5—C4—C3116.37 (14)H5'A—C5'—H5'B107.4
C5—C4—H4A108.2C7'—C6'—C5'116.02 (13)
C3—C4—H4A108.2C7'—C6'—H6'A108.3
C5—C4—H4B108.2C5'—C6'—H6'A108.3
C3—C4—H4B108.2C7'—C6'—H6'B108.3
H4A—C4—H4B107.3C5'—C6'—H6'B108.3
C4—C5—C6115.56 (13)H6'A—C6'—H6'B107.4
C4—C5—H5A108.4C6'—C7'—C8'117.95 (14)
C6—C5—H5A108.4C6'—C7'—H7'A107.8
C4—C5—H5B108.4C8'—C7'—H7'A107.8
C6—C5—H5B108.4C6'—C7'—H7'B107.8
H5A—C5—H5B107.5C8'—C7'—H7'B107.8
C7—C6—C5116.22 (14)H7'A—C7'—H7'B107.2
C7—C6—H6A108.2C2'—C8'—C7'113.35 (13)
C5—C6—H6A108.2C2'—C8'—H8'A108.9
C7—C6—H6B108.2C7'—C8'—H8'A108.9
C5—C6—H6B108.2C2'—C8'—H8'B108.9
H6A—C6—H6B107.4C7'—C8'—H8'B108.9
C6—C7—C8114.47 (13)H8'A—C8'—H8'B107.7
C6—C7—H7A108.6O2T—S1T—O1T113.43 (10)
C8—C7—H7A108.6O2T—S1T—O3T115.76 (8)
C6—C7—H7B108.6O1T—S1T—O3T115.26 (8)
C8—C7—H7B108.6O2T—S1T—C1T103.02 (9)
H7A—C7—H7B107.6O1T—S1T—C1T103.55 (8)
N1—C8—C7112.95 (13)O3T—S1T—C1T103.56 (8)
N1—C8—H8A109.0F2T—C1T—F1T109.05 (18)
C7—C8—H8A109.0F2T—C1T—F3T106.58 (15)
N1—C8—H8B109.0F1T—C1T—F3T106.99 (15)
C7—C8—H8B109.0F2T—C1T—S1T111.80 (13)
H8A—C8—H8B107.8F1T—C1T—S1T110.84 (13)
C2'—O1'—Ge1111.31 (9)F3T—C1T—S1T111.37 (12)
C1—Ge1—O1—C2−10.52 (11)C1—Ge1—C1'—N1'99.75 (13)
C1'—Ge1—O1—C2−155.34 (11)O1'—Ge1—C1'—N1'10.82 (10)
Cl1—Ge1—O1—C298.17 (10)O1—Ge1—C1'—N1'−175.80 (10)
C2—N1—C1—Ge1−11.53 (16)Cl1—Ge1—C1'—N1'−82.09 (10)
C8—N1—C1—Ge1173.22 (10)Ge1—O1'—C2'—N1'3.63 (17)
C1'—Ge1—C1—N198.61 (13)Ge1—O1'—C2'—C8'−177.63 (10)
O1'—Ge1—C1—N1−175.58 (10)C1'—N1'—C2'—O1'6.4 (2)
O1—Ge1—C1—N111.14 (9)C3'—N1'—C2'—O1'−176.72 (13)
Cl1—Ge1—C1—N1−79.52 (10)C1'—N1'—C2'—C8'−172.32 (13)
Ge1—O1—C2—N16.69 (17)C3'—N1'—C2'—C8'4.6 (2)
Ge1—O1—C2—C3−173.28 (11)C2'—N1'—C3'—C4'−98.51 (17)
C1—N1—C2—O13.3 (2)C1'—N1'—C3'—C4'78.36 (17)
C8—N1—C2—O1178.31 (14)N1'—C3'—C4'—C5'54.16 (19)
C1—N1—C2—C3−176.69 (14)C3'—C4'—C5'—C6'49.6 (2)
C8—N1—C2—C3−1.7 (2)C4'—C5'—C6'—C7'−96.25 (18)
O1—C2—C3—C4−97.02 (17)C5'—C6'—C7'—C8'73.74 (19)
N1—C2—C3—C483.01 (19)O1'—C2'—C8'—C7'−100.93 (16)
C2—C3—C4—C5−76.67 (18)N1'—C2'—C8'—C7'77.77 (19)
C3—C4—C5—C672.4 (2)C6'—C7'—C8'—C2'−77.86 (18)
C4—C5—C6—C7−99.40 (18)O2T—S1T—C1T—F2T−176.83 (13)
C5—C6—C7—C852.39 (19)O1T—S1T—C1T—F2T−58.43 (15)
C2—N1—C8—C7−93.08 (17)O3T—S1T—C1T—F2T62.20 (15)
C1—N1—C8—C781.86 (16)O2T—S1T—C1T—F1T61.27 (16)
C6—C7—C8—N152.24 (18)O1T—S1T—C1T—F1T179.67 (14)
C1—Ge1—O1'—C2'−153.47 (10)O3T—S1T—C1T—F1T−59.70 (16)
C1'—Ge1—O1'—C2'−8.70 (10)O2T—S1T—C1T—F3T−57.72 (15)
Cl1—Ge1—O1'—C2'97.24 (9)O1T—S1T—C1T—F3T60.67 (15)
C2'—N1'—C1'—Ge1−12.65 (16)O3T—S1T—C1T—F3T−178.69 (12)
C3'—N1'—C1'—Ge1170.31 (11)
Selected geometric parameters (Å, °) for (I) top
Ge1-Cl12.1678 (4)O1-Ge1-O1'173.02 (4)
Ge1-C11.941 (1)C1-Ge1-C1'144.86 (7)
Ge1-C1'1.945 (1)Ge1..O1T3.310 (2)
Ge1-O12.004 (1)Ge1..O2T3.433 (2)
Ge1-O1'1.982 (1)Ge1..Δ10.014 (1)
C2-O11.277 (2)MD Δ20.0111
C2'-O1'1.279 (2)MD Δ30.0212
C2-N11.326 (2)Ge1Δ20.301 (2)
C2'-N1'1.329 (2)Ge1Δ30.273 (2)
MD denotes the mean deviation from the plane Δn (Å). Δ1 is the plane of atoms C1/C1'/Cl1; Δ2 is the plane of atoms C1/N1/C2/O1; Δ3 is the plane of atoms C1'/N1'/C2'/O1'.
Parameters (Å, °) illustrating the ring puckering of rings B and B' top
ParameterBB'
Q20.8677 (18)0.8457 (18)
Q30.6965 (17)0.7064 (17)
Q4-0.3042 (17)-0.2890 (17)
φ2289.16 (11)290.94 (12)
φ3327.58 (14)328.10 (14)
MD Δ40.00540.0145
MD Δ50.04050.0359
Δ4 Δ5 angle68.91 (8)69.11 (8)
MD denotes the mean deviation from the plane Δn (Å). Δ4 is the plane of atoms C8/C2/N1/C3; Δ5 is the plane of atoms C7/C8/C3/C4.

B and B' correspond to the rings N1/C2–C8 and N1'/C2'–C8', respectively.
 

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