Dibromo­bis[2-(N,N-dimethyl­amino­meth­yl)phen­yl]tin(IV)

In the crystal structure of the title compound, [SnBr₂(C₉H₁₂N)₂], the Sn atom is pseudo-octa­hedrally coordinated as a result of the C,N-chelation by the 2-(N,N-dimethyl­amino­meth­yl)phenyl groups and two cis-bonded bromides. The C atoms bonded to Sn are in trans positions [C-Sn-C = 156.7 (2)°] and the coordinated N atoms are bonded in a cis fashion [N-Sn = 2.581 (5) and 2.600 (5) Å; N-Sn-N = 103.88 (16)°].

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.048
• wR factor = 0.124
• Data-to-parameter ratio = 21.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.14

Author Response: Both maximum and minimum residual densities are in close vicinity (<1A) of heavy atoms (Br2 and Sn1) and are probably resulting from defects in the crystal, which can not be properly included into the model. The poor quality of the crystal was witnessed by streaks of diffuse scattering observable on the area detector together with quick decrease of refl. intensity at high theta angles. To the lower precision of integrated intensities also contributed overall high background due to fluorescence of Br atoms and rather tricky absorption correction from irregular shape of the ''crystal''.

PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

Author Response: Low precision of refined parameters for light atoms was caused by defects in the crystal (see above).

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Dibromobis[2-(N,N-dimethylaminomethyl)phenyl]tin(IV)

Crystal data

[SnBr2(C9H12N)2]	F(000) = 1064
Mr = 546.90	Dx = 1.851 Mg m^−3
Monoclinic, P21/n	Melting point: 518 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.8370 (2) Å	Cell parameters from 23900 reflections
b = 13.3470 (3) Å	θ = 1–27.5°
c = 15.0230 (3) Å	µ = 5.38 mm^−1
β = 95.8090 (13)°	T = 150 K
V = 1962.31 (7) Å^3	Prism, colourless
Z = 4	0.25 × 0.2 × 0.12 mm

Data collection

Nonius KappaCCD area-detector diffractometer	4507 independent reflections
Radiation source: fine-focus sealed tube	3812 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.1°
φ and ω scans to fill the Ewald sphere	h = −12→12
Absorption correction: integration (Gaussian; Coppens, 1970)	k = −17→17
Tmin = 0.288, Tmax = 0.659	l = −19→19
29364 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0457P)^2 + 11.5726P] where P = (Fo^2 + 2Fc^2)/3
4507 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 3.02 e Å^−3
0 restraints	Δρmin = −1.41 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
Sn1	0.51856 (4)	0.15498 (3)	0.75437 (3)	0.02805 (12)
Br1	0.55258 (7)	0.34712 (5)	0.73016 (5)	0.04504 (19)
Br2	0.39056 (7)	0.19196 (6)	0.89550 (5)	0.0516 (2)
N1	0.6746 (5)	0.1391 (4)	0.6269 (3)	0.0342 (11)
N2	0.4426 (5)	−0.0282 (4)	0.7813 (3)	0.0353 (11)
C11	0.7168 (6)	0.1252 (4)	0.8194 (4)	0.0303 (11)
C12	0.8278 (6)	0.1429 (4)	0.7693 (4)	0.0318 (12)
C13	0.9615 (6)	0.1329 (5)	0.8096 (5)	0.0399 (14)
H13	1.0347	0.1433	0.7761	0.048*
C14	0.9852 (7)	0.1076 (5)	0.8991 (5)	0.0458 (16)
H14	1.0745	0.1029	0.9258	0.055*
C15	0.8787 (7)	0.0895 (5)	0.9488 (4)	0.0411 (14)
H15	0.8954	0.0717	1.0087	0.049*
C16	0.7432 (6)	0.0981 (5)	0.9084 (4)	0.0378 (13)
H16	0.6708	0.0853	0.9421	0.045*
C17	0.8032 (6)	0.1805 (5)	0.6735 (4)	0.0378 (13)
H17A	0.7981	0.2531	0.6736	0.045*
H17B	0.8795	0.1613	0.6410	0.045*
C18	0.7001 (8)	0.0353 (6)	0.6010 (5)	0.0503 (17)
H18A	0.6156	0.0046	0.5778	0.076*
H18B	0.7389	−0.0015	0.6524	0.076*
H18C	0.7626	0.0348	0.5559	0.076*
C19	0.6349 (8)	0.1974 (7)	0.5460 (4)	0.0534 (19)
H19A	0.6973	0.1840	0.5023	0.080*
H19B	0.6373	0.2675	0.5604	0.080*
H19C	0.5440	0.1791	0.5222	0.080*
C21	0.3429 (5)	0.1310 (4)	0.6636 (4)	0.0307 (12)
C22	0.2597 (6)	0.0495 (4)	0.6791 (4)	0.0330 (12)
C23	0.1404 (6)	0.0344 (5)	0.6218 (4)	0.0399 (14)
H23	0.0845	−0.0202	0.6308	0.048*
C24	0.1049 (6)	0.0998 (5)	0.5519 (4)	0.0397 (14)
H24	0.0242	0.0896	0.5152	0.048*
C25	0.1863 (6)	0.1789 (5)	0.5362 (5)	0.0411 (14)
H25	0.1630	0.2215	0.4881	0.049*
C26	0.3057 (6)	0.1954 (5)	0.5934 (4)	0.0383 (14)
H26	0.3606	0.2503	0.5839	0.046*
C27	0.2926 (6)	−0.0180 (5)	0.7599 (4)	0.0410 (14)
H27A	0.2530	0.0100	0.8110	0.049*
H27B	0.2526	−0.0836	0.7476	0.049*
C28	0.4924 (8)	−0.0999 (5)	0.7171 (5)	0.0514 (17)
H28A	0.5895	−0.1077	0.7295	0.077*
H28B	0.4715	−0.0751	0.6573	0.077*
H28C	0.4486	−0.1636	0.7228	0.077*
C29	0.4733 (8)	−0.0693 (6)	0.8715 (5)	0.0528 (18)
H29A	0.4250	−0.1313	0.8762	0.079*
H29B	0.4453	−0.0225	0.9146	0.079*
H29C	0.5698	−0.0812	0.8828	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02222 (19)	0.0304 (2)	0.0322 (2)	−0.00079 (14)	0.00557 (14)	−0.00554 (15)
Br1	0.0354 (3)	0.0264 (3)	0.0721 (5)	0.0022 (2)	−0.0008 (3)	−0.0050 (3)
Br2	0.0362 (3)	0.0733 (5)	0.0480 (4)	−0.0042 (3)	0.0180 (3)	−0.0266 (4)
N1	0.027 (2)	0.043 (3)	0.033 (3)	0.000 (2)	0.012 (2)	0.001 (2)
N2	0.036 (3)	0.032 (3)	0.038 (3)	−0.004 (2)	0.005 (2)	0.007 (2)
C11	0.029 (3)	0.028 (3)	0.034 (3)	0.003 (2)	0.001 (2)	−0.003 (2)
C12	0.026 (3)	0.027 (3)	0.043 (3)	0.004 (2)	0.006 (2)	−0.004 (2)
C13	0.031 (3)	0.033 (3)	0.056 (4)	0.005 (2)	0.004 (3)	−0.004 (3)
C14	0.035 (3)	0.042 (4)	0.057 (4)	0.009 (3)	−0.011 (3)	−0.009 (3)
C15	0.045 (3)	0.039 (3)	0.037 (3)	0.008 (3)	−0.005 (3)	−0.005 (3)
C16	0.040 (3)	0.036 (3)	0.038 (3)	0.005 (3)	0.007 (3)	−0.002 (3)
C17	0.025 (3)	0.042 (3)	0.047 (4)	−0.002 (2)	0.008 (3)	0.002 (3)
C18	0.055 (4)	0.052 (4)	0.046 (4)	0.003 (3)	0.015 (3)	−0.014 (3)
C19	0.049 (4)	0.078 (5)	0.036 (3)	−0.010 (4)	0.015 (3)	0.017 (3)
C21	0.024 (2)	0.031 (3)	0.038 (3)	−0.001 (2)	0.004 (2)	−0.007 (2)
C22	0.031 (3)	0.035 (3)	0.035 (3)	−0.004 (2)	0.011 (2)	−0.003 (2)
C23	0.037 (3)	0.046 (4)	0.039 (3)	−0.005 (3)	0.011 (3)	−0.002 (3)
C24	0.027 (3)	0.056 (4)	0.037 (3)	0.001 (3)	0.005 (2)	−0.006 (3)
C25	0.030 (3)	0.040 (3)	0.051 (4)	0.008 (3)	−0.003 (3)	0.005 (3)
C26	0.030 (3)	0.032 (3)	0.052 (4)	−0.001 (2)	0.001 (3)	0.003 (3)
C27	0.035 (3)	0.044 (4)	0.045 (3)	−0.012 (3)	0.009 (3)	0.006 (3)
C28	0.059 (4)	0.034 (3)	0.062 (4)	0.010 (3)	0.011 (4)	0.000 (3)
C29	0.060 (4)	0.052 (4)	0.045 (4)	−0.014 (3)	−0.001 (3)	0.018 (3)

Geometric parameters (Å, º)

Sn1—C21	2.114 (5)	C18—H18A	0.9600
Sn1—C11	2.128 (5)	C18—H18B	0.9600
Sn1—N1	2.581 (5)	C18—H18C	0.9600
Sn1—N2	2.600 (5)	C19—H19A	0.9600
Sn1—Br1	2.6164 (7)	C19—H19B	0.9600
Sn1—Br2	2.6201 (7)	C19—H19C	0.9600
N1—C19	1.463 (8)	C21—C26	1.382 (9)
N1—C18	1.468 (9)	C21—C22	1.394 (8)
N1—C17	1.488 (8)	C22—C23	1.398 (8)
N2—C29	1.466 (8)	C22—C27	1.520 (9)
N2—C28	1.477 (9)	C23—C24	1.384 (9)
N2—C27	1.484 (8)	C23—H23	0.9300
C11—C16	1.385 (8)	C24—C25	1.360 (9)
C11—C12	1.408 (8)	C24—H24	0.9300
C12—C13	1.397 (8)	C25—C26	1.400 (8)
C12—C17	1.521 (9)	C25—H25	0.9300
C13—C14	1.383 (10)	C26—H26	0.9300
C13—H13	0.9300	C27—H27A	0.9700
C14—C15	1.368 (10)	C27—H27B	0.9700
C14—H14	0.9300	C28—H28A	0.9600
C15—C16	1.412 (9)	C28—H28B	0.9600
C15—H15	0.9300	C28—H28C	0.9600
C16—H16	0.9300	C29—H29A	0.9600
C17—H17A	0.9700	C29—H29B	0.9600
C17—H17B	0.9700	C29—H29C	0.9600
C21—Sn1—C11	156.7 (2)	H17A—C17—H17B	108.0
C21—Sn1—N1	91.02 (19)	N1—C18—H18A	109.5
C11—Sn1—N1	74.87 (19)	N1—C18—H18B	109.5
C21—Sn1—N2	74.25 (19)	H18A—C18—H18B	109.5
C11—Sn1—N2	91.02 (19)	N1—C18—H18C	109.5
N1—Sn1—N2	103.88 (16)	H18A—C18—H18C	109.5
C21—Sn1—Br1	99.60 (16)	H18B—C18—H18C	109.5
C11—Sn1—Br1	97.03 (16)	N1—C19—H19A	109.5
N1—Sn1—Br1	83.30 (12)	N1—C19—H19B	109.5
N2—Sn1—Br1	170.43 (11)	H19A—C19—H19B	109.5
C21—Sn1—Br2	97.02 (15)	N1—C19—H19C	109.5
C11—Sn1—Br2	99.02 (16)	H19A—C19—H19C	109.5
N1—Sn1—Br2	170.52 (12)	H19B—C19—H19C	109.5
N2—Sn1—Br2	83.23 (12)	C26—C21—C22	119.9 (5)
Br1—Sn1—Br2	90.37 (3)	C26—C21—Sn1	122.3 (4)
C19—N1—C18	108.7 (6)	C22—C21—Sn1	117.8 (4)
C19—N1—C17	109.6 (5)	C21—C22—C23	118.7 (6)
C18—N1—C17	108.4 (5)	C21—C22—C27	120.9 (5)
C19—N1—Sn1	116.3 (4)	C23—C22—C27	120.2 (5)
C18—N1—Sn1	113.9 (4)	C24—C23—C22	120.5 (6)
C17—N1—Sn1	99.3 (3)	C24—C23—H23	119.8
C29—N2—C28	108.0 (6)	C22—C23—H23	119.8
C29—N2—C27	110.0 (5)	C25—C24—C23	120.9 (6)
C28—N2—C27	107.8 (5)	C25—C24—H24	119.5
C29—N2—Sn1	117.4 (4)	C23—C24—H24	119.5
C28—N2—Sn1	112.9 (4)	C24—C25—C26	119.2 (6)
C27—N2—Sn1	100.1 (3)	C24—C25—H25	120.4
C16—C11—C12	118.7 (5)	C26—C25—H25	120.4
C16—C11—Sn1	124.4 (4)	C21—C26—C25	120.8 (6)
C12—C11—Sn1	116.6 (4)	C21—C26—H26	119.6
C13—C12—C11	119.9 (6)	C25—C26—H26	119.6
C13—C12—C17	119.7 (5)	N2—C27—C22	110.7 (5)
C11—C12—C17	120.2 (5)	N2—C27—H27A	109.5
C14—C13—C12	120.3 (6)	C22—C27—H27A	109.5
C14—C13—H13	119.9	N2—C27—H27B	109.5
C12—C13—H13	119.9	C22—C27—H27B	109.5
C15—C14—C13	120.6 (6)	H27A—C27—H27B	108.1
C15—C14—H14	119.7	N2—C28—H28A	109.5
C13—C14—H14	119.7	N2—C28—H28B	109.5
C14—C15—C16	119.6 (6)	H28A—C28—H28B	109.5
C14—C15—H15	120.2	N2—C28—H28C	109.5
C16—C15—H15	120.2	H28A—C28—H28C	109.5
C11—C16—C15	120.8 (6)	H28B—C28—H28C	109.5
C11—C16—H16	119.6	N2—C29—H29A	109.5
C15—C16—H16	119.6	N2—C29—H29B	109.5
N1—C17—C12	111.6 (5)	H29A—C29—H29B	109.5
N1—C17—H17A	109.3	N2—C29—H29C	109.5
C12—C17—H17A	109.3	H29A—C29—H29C	109.5
N1—C17—H17B	109.3	H29B—C29—H29C	109.5
C12—C17—H17B	109.3