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The Sn atom of the title compound, [Sn(C6H5)2(C16H11Br2NO3)], adopts a distorted SnNC2O2 trigonal–bipyramidal geometry and forms five- and six-membered chelate rings with the tridentate ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015152/hb2356sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015152/hb2356Isup2.hkl
Contains datablock I

CCDC reference: 647227

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.031
  • wR factor = 0.078
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C27 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C11 -C16 1.37 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O3 .. 3.27 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O2 .. 3.35 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

[N-(3,5-Dibromo-2-oxidophenylmethylene)phenylalaninato- κ3O,N,O']diphenyltin(IV) top
Crystal data top
[Sn(C6H5)2(C16H11Br2NO3)]F(000) = 1360
Mr = 697.97Dx = 1.777 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8422 reflections
a = 11.2880 (7) Åθ = 2.4–27.4°
b = 23.3977 (15) ŵ = 4.07 mm1
c = 10.7391 (7) ÅT = 295 K
β = 113.074 (1)°Plate, yellow
V = 2609.4 (3) Å30.35 × 0.25 × 0.08 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
5406 independent reflections
Radiation source: fine-focus sealed tube4566 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1414
Tmin = 0.330, Tmax = 0.737k = 2929
20999 measured reflectionsl = 1313
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.037P)2 + 1.2833P]
where P = (Fo2 + 2Fc2)/3
5406 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = 0.44 e Å3
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
Sn10.474431 (18)0.133619 (9)0.195341 (19)0.03985 (8)
Br21.12340 (4)0.074850 (19)0.73326 (4)0.07264 (13)
Br10.68270 (4)0.211054 (19)0.64691 (4)0.07253 (13)
N10.6396 (2)0.10314 (11)0.1593 (2)0.0394 (5)
O10.6174 (2)0.17443 (9)0.3594 (2)0.0484 (5)
O20.39397 (19)0.08769 (10)0.0115 (2)0.0494 (5)
O30.4269 (2)0.03756 (10)0.1470 (2)0.0557 (6)
C10.7265 (3)0.15108 (13)0.4389 (3)0.0441 (7)
C20.7791 (3)0.16368 (14)0.5787 (3)0.0499 (7)
C30.8948 (3)0.14149 (15)0.6652 (3)0.0550 (9)
H30.92710.15060.75680.066*
C40.9629 (3)0.10560 (16)0.6150 (3)0.0537 (8)
C50.9167 (3)0.09150 (15)0.4800 (3)0.0511 (8)
H50.96370.06750.44740.061*
C60.7973 (3)0.11376 (14)0.3914 (3)0.0429 (7)
C70.7516 (3)0.09433 (13)0.2533 (3)0.0429 (7)
H70.80920.07310.22940.051*
C80.6110 (3)0.07839 (13)0.0250 (3)0.0410 (6)
H80.65810.04230.03620.049*
C90.4662 (3)0.06597 (13)0.0444 (3)0.0426 (7)
C100.6515 (3)0.11819 (15)0.0644 (3)0.0501 (8)
H10A0.62150.10240.15510.060*
H10B0.61030.15500.07010.060*
C110.7957 (3)0.12672 (15)0.0119 (3)0.0499 (8)
C120.8785 (4)0.08146 (19)0.0116 (4)0.0720 (11)
H120.84540.04460.00710.086*
C131.0095 (4)0.0894 (3)0.0621 (6)0.0999 (16)
H131.06420.05810.07790.120*
C141.0589 (5)0.1427 (4)0.0887 (6)0.118 (2)
H141.14770.14800.12490.141*
C150.9795 (6)0.1886 (3)0.0630 (6)0.1069 (19)
H151.01360.22540.07860.128*
C160.8480 (4)0.18060 (19)0.0135 (4)0.0727 (11)
H160.79390.21220.00290.087*
C170.3792 (3)0.21079 (13)0.1141 (3)0.0447 (7)
C180.3923 (4)0.25718 (17)0.1965 (4)0.0668 (10)
H180.45020.25560.28640.080*
C190.3205 (5)0.3062 (2)0.1480 (5)0.0861 (13)
H190.33060.33740.20490.103*
C200.2353 (5)0.3086 (2)0.0173 (6)0.0900 (15)
H200.18710.34160.01530.108*
C210.2202 (5)0.2632 (2)0.0660 (5)0.0924 (15)
H210.16120.26500.15530.111*
C220.2926 (4)0.21415 (18)0.0183 (4)0.0712 (11)
H220.28260.18330.07610.085*
C230.4083 (3)0.07794 (13)0.3088 (3)0.0450 (7)
C240.4279 (4)0.09094 (17)0.4403 (4)0.0639 (9)
H240.47460.12340.48100.077*
C250.3783 (4)0.0560 (2)0.5125 (4)0.0778 (12)
H250.39300.06460.60190.093*
C260.3084 (5)0.00912 (19)0.4526 (5)0.0803 (13)
H260.27320.01370.50030.096*
C270.2897 (5)0.0046 (2)0.3233 (5)0.0921 (15)
H270.24350.03730.28340.111*
C280.3392 (4)0.02979 (16)0.2516 (4)0.0668 (10)
H280.32550.02030.16300.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02674 (11)0.05319 (13)0.03667 (12)0.00029 (8)0.00925 (8)0.00585 (8)
Br20.0444 (2)0.0902 (3)0.0551 (2)0.00268 (18)0.01095 (17)0.01378 (19)
Br10.0777 (3)0.0912 (3)0.0525 (2)0.0041 (2)0.0297 (2)0.00549 (19)
N10.0281 (12)0.0524 (14)0.0339 (12)0.0021 (10)0.0080 (10)0.0030 (10)
O10.0346 (11)0.0615 (13)0.0425 (12)0.0009 (10)0.0079 (9)0.0011 (10)
O20.0277 (10)0.0711 (14)0.0427 (12)0.0028 (10)0.0066 (9)0.0045 (10)
O30.0425 (12)0.0762 (15)0.0390 (12)0.0071 (11)0.0057 (10)0.0080 (11)
C10.0349 (15)0.0535 (17)0.0388 (15)0.0083 (13)0.0087 (13)0.0054 (13)
C20.0460 (18)0.060 (2)0.0421 (17)0.0077 (15)0.0158 (14)0.0016 (15)
C30.050 (2)0.068 (2)0.0362 (16)0.0155 (16)0.0051 (15)0.0027 (15)
C40.0331 (16)0.068 (2)0.0436 (18)0.0073 (15)0.0032 (14)0.0078 (16)
C50.0315 (15)0.068 (2)0.0426 (17)0.0032 (14)0.0017 (13)0.0059 (15)
C60.0283 (14)0.0591 (18)0.0347 (15)0.0051 (13)0.0052 (12)0.0045 (13)
C70.0308 (15)0.0561 (18)0.0399 (15)0.0011 (13)0.0119 (13)0.0055 (13)
C80.0306 (14)0.0543 (17)0.0329 (14)0.0001 (12)0.0069 (12)0.0015 (12)
C90.0322 (15)0.0554 (18)0.0335 (15)0.0002 (13)0.0055 (12)0.0085 (13)
C100.0390 (17)0.069 (2)0.0396 (16)0.0051 (15)0.0124 (14)0.0032 (15)
C110.0410 (17)0.075 (2)0.0370 (16)0.0115 (16)0.0185 (14)0.0060 (15)
C120.047 (2)0.091 (3)0.078 (3)0.000 (2)0.025 (2)0.011 (2)
C130.046 (2)0.140 (5)0.116 (4)0.007 (3)0.034 (3)0.012 (4)
C140.045 (3)0.189 (7)0.113 (5)0.031 (4)0.026 (3)0.021 (4)
C150.086 (4)0.133 (5)0.097 (4)0.059 (4)0.032 (3)0.038 (4)
C160.069 (3)0.085 (3)0.064 (2)0.021 (2)0.026 (2)0.015 (2)
C170.0355 (16)0.0569 (18)0.0435 (16)0.0040 (13)0.0173 (13)0.0106 (14)
C180.064 (2)0.071 (2)0.063 (2)0.0108 (19)0.0218 (19)0.0032 (19)
C190.088 (3)0.074 (3)0.092 (3)0.023 (2)0.030 (3)0.004 (2)
C200.084 (3)0.078 (3)0.109 (4)0.033 (3)0.039 (3)0.034 (3)
C210.091 (3)0.099 (4)0.066 (3)0.029 (3)0.008 (2)0.034 (3)
C220.076 (3)0.073 (2)0.052 (2)0.011 (2)0.012 (2)0.0107 (18)
C230.0348 (15)0.0563 (18)0.0434 (16)0.0022 (13)0.0148 (13)0.0091 (14)
C240.069 (2)0.072 (2)0.055 (2)0.0122 (19)0.0292 (19)0.0002 (18)
C250.089 (3)0.096 (3)0.062 (2)0.001 (3)0.044 (2)0.016 (2)
C260.089 (3)0.079 (3)0.089 (3)0.008 (2)0.051 (3)0.025 (2)
C270.108 (4)0.082 (3)0.094 (3)0.035 (3)0.049 (3)0.005 (3)
C280.075 (3)0.069 (2)0.062 (2)0.019 (2)0.033 (2)0.0006 (19)
Geometric parameters (Å, º) top
Sn1—O12.095 (2)C12—H120.9300
Sn1—C172.107 (3)C13—C141.350 (8)
Sn1—C232.110 (3)C13—H130.9300
Sn1—O22.114 (2)C14—C151.356 (8)
Sn1—N12.168 (2)C14—H140.9300
Br2—C41.900 (3)C15—C161.380 (7)
Br1—C21.891 (3)C15—H150.9300
N1—C71.288 (4)C16—H160.9300
N1—C81.468 (4)C17—C181.371 (5)
O1—C11.311 (4)C17—C221.376 (5)
O2—C91.292 (4)C18—C191.383 (6)
O3—C91.212 (4)C18—H180.9300
C1—C61.407 (5)C19—C201.357 (7)
C1—C21.413 (4)C19—H190.9300
C2—C31.374 (5)C20—C211.357 (7)
C3—C41.382 (5)C20—H200.9300
C3—H30.9300C21—C221.385 (6)
C4—C51.375 (4)C21—H210.9300
C5—C61.410 (4)C22—H220.9300
C5—H50.9300C23—C281.371 (5)
C6—C71.440 (4)C23—C241.375 (5)
C7—H70.9300C24—C251.387 (5)
C8—C101.531 (4)C24—H240.9300
C8—C91.535 (4)C25—C261.356 (6)
C8—H80.9800C25—H250.9300
C10—C111.512 (4)C26—C271.358 (6)
C10—H10A0.9700C26—H260.9300
C10—H10B0.9700C27—C281.375 (5)
C11—C121.369 (5)C27—H270.9300
C11—C161.373 (5)C28—H280.9300
C12—C131.374 (6)
O1—Sn1—C1793.28 (10)C16—C11—C10120.8 (3)
O1—Sn1—C2397.24 (10)C11—C12—C13121.3 (4)
C17—Sn1—C23121.98 (11)C11—C12—H12119.3
O1—Sn1—O2157.50 (8)C13—C12—H12119.3
C17—Sn1—O294.95 (11)C14—C13—C12120.0 (5)
C23—Sn1—O296.06 (11)C14—C13—H13120.0
O1—Sn1—N182.35 (8)C12—C13—H13120.0
C17—Sn1—N1122.87 (10)C13—C14—C15120.2 (5)
C23—Sn1—N1115.06 (10)C13—C14—H14119.9
O2—Sn1—N175.59 (8)C15—C14—H14119.9
C7—N1—C8118.5 (2)C14—C15—C16119.7 (5)
C7—N1—Sn1124.2 (2)C14—C15—H15120.1
C8—N1—Sn1115.56 (17)C16—C15—H15120.1
C1—O1—Sn1125.1 (2)C11—C16—C15121.1 (5)
C9—O2—Sn1121.04 (18)C11—C16—H16119.5
O1—C1—C6123.0 (3)C15—C16—H16119.5
O1—C1—C2120.1 (3)C18—C17—C22118.3 (3)
C6—C1—C2116.9 (3)C18—C17—Sn1120.2 (2)
C3—C2—C1122.1 (3)C22—C17—Sn1121.1 (3)
C3—C2—Br1119.9 (3)C17—C18—C19121.0 (4)
C1—C2—Br1117.9 (2)C17—C18—H18119.5
C2—C3—C4119.5 (3)C19—C18—H18119.5
C2—C3—H3120.2C20—C19—C18119.8 (5)
C4—C3—H3120.2C20—C19—H19120.1
C5—C4—C3121.2 (3)C18—C19—H19120.1
C5—C4—Br2118.8 (3)C19—C20—C21120.3 (4)
C3—C4—Br2120.0 (2)C19—C20—H20119.8
C4—C5—C6119.4 (3)C21—C20—H20119.8
C4—C5—H5120.3C20—C21—C22120.1 (4)
C6—C5—H5120.3C20—C21—H21119.9
C1—C6—C5120.9 (3)C22—C21—H21119.9
C1—C6—C7123.0 (3)C17—C22—C21120.5 (4)
C5—C6—C7116.1 (3)C17—C22—H22119.8
N1—C7—C6127.0 (3)C21—C22—H22119.8
N1—C7—H7116.5C28—C23—C24118.4 (3)
C6—C7—H7116.5C28—C23—Sn1121.1 (2)
N1—C8—C10111.8 (2)C24—C23—Sn1120.4 (3)
N1—C8—C9109.5 (2)C23—C24—C25120.4 (4)
C10—C8—C9109.5 (2)C23—C24—H24119.8
N1—C8—H8108.6C25—C24—H24119.8
C10—C8—H8108.6C26—C25—C24119.9 (4)
C9—C8—H8108.6C26—C25—H25120.0
O3—C9—O2124.4 (3)C24—C25—H25120.0
O3—C9—C8119.1 (3)C25—C26—C27120.3 (4)
O2—C9—C8116.5 (3)C25—C26—H26119.9
C11—C10—C8112.9 (3)C27—C26—H26119.9
C11—C10—H10A109.0C26—C27—C28120.0 (4)
C8—C10—H10A109.0C26—C27—H27120.0
C11—C10—H10B109.0C28—C27—H27120.0
C8—C10—H10B109.0C23—C28—C27121.0 (4)
H10A—C10—H10B107.8C23—C28—H28119.5
C12—C11—C16117.6 (4)C27—C28—H28119.5
C12—C11—C10121.6 (3)
O1—Sn1—N1—C730.4 (2)N1—C8—C9—O211.9 (4)
C17—Sn1—N1—C7119.4 (3)C10—C8—C9—O2111.0 (3)
C23—Sn1—N1—C764.0 (3)N1—C8—C10—C1165.6 (3)
O2—Sn1—N1—C7154.0 (3)C9—C8—C10—C11172.8 (3)
O1—Sn1—N1—C8165.0 (2)C8—C10—C11—C1256.0 (4)
C17—Sn1—N1—C876.0 (2)C8—C10—C11—C16124.3 (3)
C23—Sn1—N1—C8100.6 (2)C16—C11—C12—C131.7 (6)
O2—Sn1—N1—C810.54 (19)C10—C11—C12—C13178.6 (4)
C17—Sn1—O1—C1165.2 (2)C11—C12—C13—C140.4 (8)
C23—Sn1—O1—C172.0 (2)C12—C13—C14—C151.5 (9)
O2—Sn1—O1—C153.8 (4)C13—C14—C15—C162.1 (9)
N1—Sn1—O1—C142.5 (2)C12—C11—C16—C151.0 (6)
O1—Sn1—O2—C97.8 (4)C10—C11—C16—C15179.2 (4)
C17—Sn1—O2—C9118.9 (2)C14—C15—C16—C110.8 (8)
C23—Sn1—O2—C9118.2 (2)O1—Sn1—C17—C1824.7 (3)
N1—Sn1—O2—C93.8 (2)C23—Sn1—C17—C1876.0 (3)
Sn1—O1—C1—C638.0 (4)O2—Sn1—C17—C18176.3 (3)
Sn1—O1—C1—C2142.9 (2)N1—Sn1—C17—C18107.7 (3)
O1—C1—C2—C3178.2 (3)O1—Sn1—C17—C22162.3 (3)
C6—C1—C2—C30.9 (5)C23—Sn1—C17—C2297.1 (3)
O1—C1—C2—Br13.6 (4)O2—Sn1—C17—C223.3 (3)
C6—C1—C2—Br1177.3 (2)N1—Sn1—C17—C2279.3 (3)
C1—C2—C3—C40.0 (5)C22—C17—C18—C190.1 (6)
Br1—C2—C3—C4178.2 (2)Sn1—C17—C18—C19173.4 (3)
C2—C3—C4—C50.2 (5)C17—C18—C19—C200.3 (7)
C2—C3—C4—Br2179.7 (2)C18—C19—C20—C210.0 (8)
C3—C4—C5—C60.5 (5)C19—C20—C21—C220.5 (8)
Br2—C4—C5—C6179.6 (2)C18—C17—C22—C210.4 (6)
O1—C1—C6—C5177.5 (3)Sn1—C17—C22—C21172.8 (3)
C2—C1—C6—C51.6 (5)C20—C21—C22—C170.7 (7)
O1—C1—C6—C74.9 (5)O1—Sn1—C23—C28160.7 (3)
C2—C1—C6—C7176.0 (3)C17—Sn1—C23—C28100.8 (3)
C4—C5—C6—C11.4 (5)O2—Sn1—C23—C281.1 (3)
C4—C5—C6—C7176.4 (3)N1—Sn1—C23—C2875.8 (3)
C8—N1—C7—C6178.6 (3)O1—Sn1—C23—C2422.9 (3)
Sn1—N1—C7—C614.5 (4)C17—Sn1—C23—C2475.6 (3)
C1—C6—C7—N16.8 (5)O2—Sn1—C23—C24175.3 (3)
C5—C6—C7—N1170.9 (3)N1—Sn1—C23—C24107.8 (3)
C7—N1—C8—C1087.8 (3)C28—C23—C24—C250.1 (6)
Sn1—N1—C8—C10106.7 (2)Sn1—C23—C24—C25176.5 (3)
C7—N1—C8—C9150.7 (3)C23—C24—C25—C261.0 (7)
Sn1—N1—C8—C914.8 (3)C24—C25—C26—C271.8 (7)
Sn1—O2—C9—O3177.3 (2)C25—C26—C27—C281.5 (8)
Sn1—O2—C9—C83.5 (3)C24—C23—C28—C270.4 (6)
N1—C8—C9—O3168.8 (3)Sn1—C23—C28—C27176.1 (4)
C10—C8—C9—O368.2 (4)C26—C27—C28—C230.4 (7)
 

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