Tetra­kis(2,4,6-tri­methyl­anilido)tin(IV)

Transamination of Sn(NMe₂)₄ with H₂NMes (Mes is 2,4,6-tri­methyl­phenyl, C₉H₁₁) led to the formation of the title compound, [Sn(C₉H₁₂N)₄] or Sn(NHMes)₄, which crystallizes in the tetra­gonal space group P2₁c, with four formula units per unit cell. The mol­ecular structure consists of a central tin(IV) atom, which is surrounded by four NHMes groups. Sn(NHMes)₄ possesses crystallographically imposed symmetry. The SnN₄ coordination polyhedron is best described as a compressed bis­phenoid.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.022
• wR factor = 0.057
• Data-to-parameter ratio = 22.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N        --H        .     Please Check

Alert level G
PLAT069_ALERT_1_G Atom Label Without Numerical Part ..............         Sn Do !
PLAT069_ALERT_1_G Atom Label Without Numerical Part ..............          N Do !
PLAT069_ALERT_1_G Atom Label Without Numerical Part ..............          H Do !
PLAT794_ALERT_5_G Tentative Bond Valency for Sn        (IV)      .       3.96 Info
PLAT795_ALERT_4_G C-Atom in CIF Coordinate List Out-of-Sequence ..         C6 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
                5  9 10,
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       3.53 Note
              Predicted wR2: Based on SigI   2  1.62 or SHELX Weight  5.46       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Tetrakis(2,4,6-trimethylanilido)tin(IV)

Crystal data

[Sn(C9H12N)4]	Dx = 1.331 Mg m^−3
Mr = 655.47	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421c	Cell parameters from 28663 reflections
a = 13.7000 (6) Å	θ = 29.7–1.5°
c = 8.7123 (5) Å	µ = 0.81 mm^−1
V = 1635.21 (17) Å^3	T = 170 K
Z = 2	Block, colourless
F(000) = 684	0.50 × 0.35 × 0.30 mm

Data collection

Stoe IPDS 2 diffractometer	2049 reflections with I > 2σ(I)
rotation scans	Rint = 0.053
Absorption correction: integration [X-Red32 (Stoe & Cie, 2016), by Gaussian integration analogous to Coppens (1970)]	θmax = 29.2°, θmin = 2.1°
Tmin = 0.735, Tmax = 0.898	h = −18→18
30518 measured reflections	k = −18→17
2205 independent reflections	l = −11→11

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0329P)^2 + 0.2402P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.057	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.42 e Å^−3
2205 reflections	Δρmin = −0.21 e Å^−3
100 parameters	Absolute structure: Flack x determined using 832 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.036 (19)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The amino hydrogen atom was located from a difference-Fourier map and was refined freely.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn	0.500000	0.500000	0.500000	0.03205 (9)
N	0.38602 (14)	0.43981 (15)	0.3843 (2)	0.0398 (4)
H	0.337 (2)	0.464 (2)	0.414 (3)	0.058 (9)*
C9	0.51845 (19)	0.3557 (2)	0.1674 (3)	0.0523 (6)
H9A	0.485199	0.412240	0.122563	0.078*
H9B	0.547813	0.316490	0.085463	0.078*
H9C	0.569620	0.378157	0.237652	0.078*
C6	0.44600 (16)	0.29472 (16)	0.2542 (3)	0.0419 (4)
C5	0.44012 (18)	0.19474 (18)	0.2270 (3)	0.0479 (5)
H5	0.487138	0.165100	0.161838	0.057*
C4	0.36777 (19)	0.13675 (17)	0.2921 (3)	0.0508 (6)
C1	0.37965 (16)	0.33771 (16)	0.3564 (3)	0.0368 (4)
C8	0.3612 (3)	0.0293 (2)	0.2557 (5)	0.0782 (10)
H8A	0.406218	−0.007008	0.321874	0.117*
H8B	0.378659	0.018516	0.147944	0.117*
H8C	0.294318	0.006481	0.273615	0.117*
C3	0.30148 (17)	0.18170 (18)	0.3885 (3)	0.0478 (5)
H3	0.250913	0.143525	0.432859	0.057*
C2	0.30595 (18)	0.28038 (19)	0.4231 (3)	0.0407 (5)
C7	0.23079 (19)	0.3233 (2)	0.5301 (3)	0.0512 (6)
H7A	0.185274	0.363947	0.471476	0.077*
H7B	0.263505	0.363313	0.607882	0.077*
H7C	0.194779	0.270463	0.580599	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn	0.02775 (10)	0.02775 (10)	0.04063 (14)	0.000	0.000	0.000
N	0.0305 (9)	0.0343 (9)	0.0544 (11)	−0.0004 (7)	−0.0056 (8)	−0.0023 (8)
C9	0.0519 (14)	0.0485 (13)	0.0566 (13)	−0.0059 (10)	0.0118 (11)	−0.0064 (11)
C6	0.0410 (11)	0.0387 (10)	0.0461 (11)	−0.0019 (8)	−0.0044 (9)	−0.0037 (9)
C5	0.0462 (12)	0.0426 (11)	0.0548 (13)	−0.0015 (10)	−0.0049 (11)	−0.0089 (10)
C4	0.0508 (14)	0.0347 (11)	0.0668 (15)	−0.0026 (9)	−0.0158 (12)	−0.0035 (10)
C1	0.0334 (10)	0.0331 (10)	0.0440 (11)	−0.0022 (8)	−0.0081 (9)	0.0005 (8)
C8	0.074 (2)	0.0391 (13)	0.121 (3)	−0.0126 (13)	−0.007 (2)	−0.0154 (17)
C3	0.0429 (12)	0.0410 (11)	0.0596 (14)	−0.0117 (10)	−0.0119 (11)	0.0084 (11)
C2	0.0362 (11)	0.0399 (12)	0.0459 (13)	−0.0038 (9)	−0.0091 (10)	0.0047 (10)
C7	0.0431 (11)	0.0516 (13)	0.0591 (16)	−0.0067 (10)	0.0046 (10)	0.0035 (11)

Geometric parameters (Å, º)

Sn—N	2.0332 (19)	C5—H5	0.9500
Sn—N^i	2.0332 (19)	C4—C3	1.382 (4)
Sn—N^ii	2.0332 (19)	C4—C8	1.509 (3)
Sn—N^iii	2.0332 (19)	C1—C2	1.405 (3)
N—C1	1.422 (3)	C8—H8A	0.9800
N—H	0.79 (3)	C8—H8B	0.9800
C9—C6	1.502 (3)	C8—H8C	0.9800
C9—H9A	0.9800	C3—C2	1.386 (3)
C9—H9B	0.9800	C3—H3	0.9500
C9—H9C	0.9800	C2—C7	1.509 (4)
C6—C5	1.392 (3)	C7—H7A	0.9800
C6—C1	1.402 (3)	C7—H7B	0.9800
C5—C4	1.391 (4)	C7—H7C	0.9800
N—Sn—N^i	104.22 (5)	C5—C4—C8	121.0 (3)
N—Sn—N^ii	120.57 (12)	C6—C1—C2	119.6 (2)
N^i—Sn—N^ii	104.22 (5)	C6—C1—N	118.8 (2)
N—Sn—N^iii	104.22 (5)	C2—C1—N	121.6 (2)
N^i—Sn—N^iii	120.57 (12)	C4—C8—H8A	109.5
N^ii—Sn—N^iii	104.22 (5)	C4—C8—H8B	109.5
C1—N—Sn	122.05 (15)	H8A—C8—H8B	109.5
C1—N—H	114 (2)	C4—C8—H8C	109.5
Sn—N—H	109 (2)	H8A—C8—H8C	109.5
C6—C9—H9A	109.5	H8B—C8—H8C	109.5
C6—C9—H9B	109.5	C4—C3—C2	122.5 (2)
H9A—C9—H9B	109.5	C4—C3—H3	118.7
C6—C9—H9C	109.5	C2—C3—H3	118.7
H9A—C9—H9C	109.5	C3—C2—C1	119.2 (2)
H9B—C9—H9C	109.5	C3—C2—C7	118.9 (2)
C5—C6—C1	118.9 (2)	C1—C2—C7	121.9 (2)
C5—C6—C9	120.0 (2)	C2—C7—H7A	109.5
C1—C6—C9	121.0 (2)	C2—C7—H7B	109.5
C4—C5—C6	122.3 (2)	H7A—C7—H7B	109.5
C4—C5—H5	118.9	C2—C7—H7C	109.5
C6—C5—H5	118.9	H7A—C7—H7C	109.5
C3—C4—C5	117.5 (2)	H7B—C7—H7C	109.5
C3—C4—C8	121.5 (3)
C1—C6—C5—C4	3.2 (4)	Sn—N—C1—C2	114.2 (2)
C9—C6—C5—C4	−173.1 (2)	C5—C4—C3—C2	−1.0 (4)
C6—C5—C4—C3	−1.1 (4)	C8—C4—C3—C2	−179.7 (3)
C6—C5—C4—C8	177.7 (3)	C4—C3—C2—C1	0.9 (4)
C5—C6—C1—C2	−3.2 (3)	C4—C3—C2—C7	−179.7 (2)
C9—C6—C1—C2	173.1 (2)	C6—C1—C2—C3	1.2 (3)
C5—C6—C1—N	179.8 (2)	N—C1—C2—C3	178.2 (2)
C9—C6—C1—N	−3.9 (3)	C6—C1—C2—C7	−178.2 (2)
Sn—N—C1—C6	−68.8 (3)	N—C1—C2—C7	−1.2 (4)

Symmetry codes: (i) y, −x+1, −z+1; (ii) −x+1, −y+1, z; (iii) −y+1, x, −z+1.