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The title compound, [Ge(C6H5)3(N3)], (I), is monomeric with quasi-tetrahedral geometry around germanium. The azide group (—Nα—Nβ—Nγ) is disordered. One form has d(Nα—Nβ) > d(Nβ—Nγ), the other has d(Nα—Nβ) < d(Nβ—Nγ). In contrast, the mesityl analogue, (II), has d(Nα—Nβ) > d(Nβ—Nγ). As expected, on going from (I) to (II), angle (C—Ge—C)ave increases while angle (C—Ge—Nα)ave decreases. However, in contrast to the silicon case, d(Ge—Nα) and d(Ge—C)ave remain effectively unchanged on going from (I) to (II).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021221/ci6432sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021221/ci6432Isup2.hkl
Contains datablock I

CCDC reference: 252747

Key indicators

  • Single-crystal X-ray study
  • T = 220 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.101
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors for N32
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N21 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (Maris, 2004).

azidotriphenylgermane top
Crystal data top
[Ge(C6H5)3(N3)]F(000) = 704
Mr = 345.92Dx = 1.423 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ynCell parameters from 11289 reflections
a = 9.7428 (2) Åθ = 4.6–72.9°
b = 17.0689 (3) ŵ = 2.56 mm1
c = 10.3630 (2) ÅT = 220 K
β = 110.449 (1)°Block, colourless
V = 1614.76 (5) Å30.50 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker AXS SMART 2K/Platform
diffractometer
3097 independent reflections
Radiation source: Sealed Tube2939 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 5.5 pixels mm-1θmax = 73.0°, θmin = 5.2°
ω scansh = 1211
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2020
Tmin = 0.403, Tmax = 0.681l = 1212
13062 measured reflections
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.084P)2]
where P = (Fo2 + 2Fc2)/3
3097 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.29 e Å3
48 restraintsΔρmin = 0.62 e Å3
Special details top

Experimental. X-ray crystallographic data for (A) were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2 K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu—Kα radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8 Å resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis.

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*/UeqOcc. (<1)
Ge0.601550 (19)0.157792 (10)0.247136 (18)0.03403 (12)
N10.5977 (2)0.07986 (10)0.11545 (17)0.0478 (4)
N210.714 (2)0.0634 (12)0.099 (2)0.050 (2)0.50
N310.8132 (12)0.0394 (6)0.0859 (10)0.080 (2)0.50
N220.695 (3)0.0702 (13)0.081 (3)0.070 (6)0.50
N320.7848 (14)0.0630 (7)0.0263 (11)0.100 (3)0.50
C110.39515 (19)0.17474 (11)0.20953 (19)0.0394 (4)
C120.2910 (2)0.12018 (13)0.1358 (2)0.0505 (5)
H120.32070.07330.10580.061*
C130.1436 (3)0.1353 (2)0.1067 (3)0.0709 (7)
H130.07350.09910.05440.085*
C140.0981 (3)0.20283 (19)0.1535 (3)0.0734 (8)
H140.00210.21180.13530.088*
C150.2001 (3)0.25657 (17)0.2266 (3)0.0700 (7)
H150.16940.30280.25790.084*
C160.3488 (3)0.24339 (13)0.2549 (2)0.0520 (5)
H160.41800.28070.30470.062*
C210.70042 (18)0.24861 (9)0.20908 (16)0.0343 (3)
C220.6816 (2)0.27043 (11)0.07444 (18)0.0399 (4)
H220.62570.23860.00080.048*
C230.7443 (3)0.33838 (10)0.0478 (2)0.0458 (4)
H230.73190.35230.04330.055*
C240.8252 (2)0.38585 (10)0.1558 (2)0.0456 (4)
H240.86640.43260.13780.055*
C250.8457 (2)0.36478 (12)0.2900 (2)0.0473 (4)
H250.90160.39690.36320.057*
C260.7842 (2)0.29643 (11)0.31699 (18)0.0424 (4)
H260.79890.28220.40850.051*
C310.7044 (2)0.11211 (10)0.42617 (17)0.0368 (3)
C320.8547 (2)0.10394 (12)0.4735 (2)0.0478 (4)
H320.90830.12270.42010.057*
C330.9273 (2)0.06822 (13)0.5993 (2)0.0562 (5)
H331.02980.06310.63120.067*
C340.8488 (3)0.04029 (13)0.6771 (2)0.0561 (5)
H340.89790.01640.76250.067*
C350.6988 (2)0.04728 (13)0.6303 (2)0.0533 (5)
H350.64540.02700.68280.064*
C360.6261 (2)0.08424 (11)0.50562 (19)0.0440 (4)
H360.52380.09040.47510.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ge0.03553 (18)0.03323 (17)0.03152 (17)0.00267 (5)0.00942 (12)0.00067 (5)
N10.0491 (10)0.0462 (8)0.0462 (9)0.0038 (7)0.0142 (8)0.0138 (7)
N210.043 (4)0.049 (3)0.062 (5)0.004 (3)0.022 (4)0.016 (3)
N310.052 (3)0.089 (5)0.101 (6)0.004 (3)0.028 (4)0.038 (4)
N220.071 (9)0.062 (7)0.072 (7)0.011 (5)0.017 (6)0.038 (6)
N320.090 (7)0.109 (8)0.123 (8)0.021 (5)0.066 (7)0.059 (6)
C110.0372 (9)0.0429 (8)0.0357 (9)0.0023 (7)0.0098 (7)0.0123 (7)
C120.0428 (10)0.0556 (11)0.0466 (10)0.0085 (8)0.0076 (8)0.0112 (8)
C130.0439 (13)0.0951 (19)0.0633 (14)0.0141 (12)0.0057 (11)0.0295 (14)
C140.0445 (12)0.0979 (19)0.0799 (16)0.0197 (12)0.0242 (12)0.0481 (15)
C150.0674 (16)0.0741 (15)0.0806 (16)0.0298 (12)0.0412 (14)0.0367 (13)
C160.0532 (11)0.0484 (10)0.0576 (11)0.0088 (8)0.0233 (9)0.0117 (9)
C210.0340 (8)0.0347 (8)0.0336 (7)0.0007 (6)0.0111 (7)0.0014 (6)
C220.0418 (9)0.0429 (9)0.0340 (8)0.0020 (7)0.0119 (7)0.0022 (7)
C230.0508 (12)0.0456 (11)0.0445 (10)0.0023 (7)0.0210 (9)0.0068 (6)
C240.0445 (10)0.0364 (8)0.0595 (11)0.0028 (6)0.0228 (9)0.0031 (7)
C250.0453 (10)0.0417 (9)0.0486 (10)0.0067 (8)0.0084 (8)0.0079 (8)
C260.0493 (10)0.0402 (8)0.0344 (8)0.0033 (7)0.0103 (7)0.0012 (6)
C310.0391 (9)0.0331 (8)0.0345 (8)0.0004 (6)0.0084 (7)0.0004 (6)
C320.0401 (10)0.0524 (10)0.0486 (10)0.0015 (7)0.0125 (8)0.0076 (8)
C330.0407 (11)0.0584 (12)0.0596 (12)0.0030 (8)0.0049 (9)0.0121 (9)
C340.0583 (13)0.0522 (11)0.0461 (10)0.0009 (9)0.0037 (9)0.0152 (9)
C350.0581 (12)0.0570 (11)0.0454 (10)0.0018 (9)0.0188 (9)0.0122 (8)
C360.0418 (10)0.0467 (9)0.0427 (9)0.0002 (7)0.0139 (8)0.0032 (7)
Geometric parameters (Å, º) top
Ge—N11.8968 (17)C22—C231.383 (3)
Ge—C111.9317 (18)C22—H220.94
Ge—C211.9370 (16)C23—C241.383 (3)
Ge—C311.9378 (17)C23—H230.94
N1—N221.14 (2)C24—C251.382 (3)
N1—N211.24 (2)C24—H240.94
N21—N311.10 (2)C25—C261.384 (3)
N22—N321.20 (3)C25—H250.94
C11—C121.392 (3)C26—H260.94
C11—C161.395 (3)C31—C321.379 (3)
C12—C131.385 (3)C31—C361.388 (3)
C12—H120.94C32—C331.388 (3)
C13—C141.382 (5)C32—H320.94
C13—H130.94C33—C341.376 (3)
C14—C151.370 (4)C33—H330.94
C14—H140.94C34—C351.375 (3)
C15—C161.392 (3)C34—H340.94
C15—H150.94C35—C361.389 (3)
C16—H160.94C35—H350.94
C21—C221.393 (2)C36—H360.94
C21—C261.395 (2)
N1—Ge—C11101.69 (9)C23—C22—H22119.6
N1—Ge—C21107.51 (7)C21—C22—H22119.6
C11—Ge—C21113.31 (7)C22—C23—C24119.79 (19)
N1—Ge—C31106.27 (7)C22—C23—H23120.1
C11—Ge—C31114.02 (7)C24—C23—H23120.1
C21—Ge—C31112.91 (7)C25—C24—C23120.18 (17)
N22—N1—Ge121.3 (1)C25—C24—H24119.9
N21—N1—Ge118.1 (9)C23—C24—H24119.9
N31—N21—N1171.20 (19)C24—C25—C26120.13 (17)
N1—N22—N32171 (3)C24—C25—H25119.9
C12—C11—C16119.15 (19)C26—C25—H25119.9
C12—C11—Ge121.20 (16)C25—C26—C21120.32 (17)
C16—C11—Ge119.64 (15)C25—C26—H26119.8
C13—C12—C11119.7 (2)C21—C26—H26119.8
C13—C12—H12120.1C32—C31—C36119.35 (16)
C11—C12—H12120.1C32—C31—Ge120.72 (14)
C14—C13—C12121.0 (3)C36—C31—Ge119.88 (14)
C14—C13—H13119.5C31—C32—C33120.51 (18)
C12—C13—H13119.5C31—C32—H32119.7
C15—C14—C13119.5 (2)C33—C32—H32119.7
C15—C14—H14120.2C34—C33—C32119.8 (2)
C13—C14—H14120.2C34—C33—H33120.1
C14—C15—C16120.6 (3)C32—C33—H33120.1
C14—C15—H15119.7C35—C34—C33120.21 (18)
C16—C15—H15119.7C35—C34—H34119.9
C15—C16—C11120.0 (2)C33—C34—H34119.9
C15—C16—H16120C34—C35—C36120.09 (19)
C11—C16—H16120C34—C35—H35120
C22—C21—C26118.82 (16)C36—C35—H35120
C22—C21—Ge121.14 (12)C31—C36—C35119.99 (18)
C26—C21—Ge119.89 (13)C31—C36—H36120
C23—C22—C21120.76 (17)C35—C36—H36120
C11—Ge—N1—N22158.20 (16)C11—Ge—C21—C26101.09 (15)
C21—Ge—N1—N2238.90 (16)C31—Ge—C21—C2630.47 (16)
C31—Ge—N1—N2282.20 (16)C26—C21—C22—C230.2 (3)
C11—Ge—N1—N21169.90 (12)Ge—C21—C22—C23175.41 (14)
C21—Ge—N1—N2150.60 (12)C21—C22—C23—C240.7 (3)
C31—Ge—N1—N2170.60 (12)C22—C23—C24—C251.2 (3)
N1—Ge—C11—C1218.08 (17)C23—C24—C25—C260.6 (3)
C21—Ge—C11—C12133.15 (14)C24—C25—C26—C210.4 (3)
C31—Ge—C11—C1295.84 (16)C22—C21—C26—C250.8 (3)
N1—Ge—C11—C16160.86 (15)Ge—C21—C26—C25174.90 (15)
C21—Ge—C11—C1645.80 (17)N1—Ge—C31—C3275.48 (16)
C31—Ge—C11—C1685.21 (16)C11—Ge—C31—C32173.35 (14)
C16—C11—C12—C131.0 (3)C21—Ge—C31—C3242.14 (17)
Ge—C11—C12—C13177.91 (15)N1—Ge—C31—C36101.80 (15)
C11—C12—C13—C142.0 (3)C11—Ge—C31—C369.37 (17)
C12—C13—C14—C151.7 (4)C21—Ge—C31—C36140.57 (14)
C13—C14—C15—C160.5 (3)C36—C31—C32—C330.0 (3)
C14—C15—C16—C110.4 (3)Ge—C31—C32—C33177.31 (16)
C12—C11—C16—C150.1 (3)C31—C32—C33—C340.4 (3)
Ge—C11—C16—C15179.10 (16)C32—C33—C34—C350.3 (4)
N1—Ge—C21—C2237.05 (16)C33—C34—C35—C361.5 (4)
C11—Ge—C21—C2274.50 (16)C32—C31—C36—C351.1 (3)
C31—Ge—C21—C22153.95 (14)Ge—C31—C36—C35176.18 (15)
N1—Ge—C21—C26147.37 (14)C34—C35—C36—C311.9 (3)
 

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