share
share
Issue contentsclose
Statistics
close
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Supporting information
Supporting informationclose
Download PDF of article
Download PDF of articleclose
Acta Cryst. (2007). E63, m1843
https://doi.org/10.1107/S1600536807027298
Download PDF of article
Download PDF of articleclose
Supporting information
Supporting informationclose
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Statistics
close
Issue contentsclose
share
link to html

{(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino­methyl]benzoato}triphenyl­tin(IV)

X.-N. Fang, Y. Sui, R.-H. Hu, Q.-Y. Luo and H.-Q. Qin
The title compound, [Sn(C6H5)3(C19H16N3O3)], is a four-coordinate SnIV complex, with a distorted tetra­hedral geometry and one disordered (0.54:0.46) phenyl ring. The Schiff base carboxyl­ate group acts as a monodentate ligand coordinating through the deprotonated hydroxyl O atom. In the crystal structure, a weak offset face-to-face aromatic π–π stacking inter­action can be found between the pyrazole ring and the benzene ring of 4-formyl­benzoic acid. The centroid-to-centroid distance is 3.858 (2) Å and the interplanar distance is 3.375 (4) Å.
Read articleSimilar articles

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027298/si2019sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027298/si2019Isup2.hkl
Contains datablock I

CCDC reference: 655588

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.023
  • wR factor = 0.060
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found




Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93
Author Response: This alarm is due to the lattice defects of my sample. To solve this problem, two samples were screened. The selected sample exhibited the better diffraction behavior. 
PLAT432_ALERT_2_A Short Inter X...Y Contact  C36    ..  C36     ..       2.54 Ang.
Author Response: This alarm is due to the disordered phenyl. 

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _diffrn_reflns_theta_full          25.00
           From the CIF: _reflns_number_total               5246
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5670
           Completeness (_total/calc)             92.52%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C29
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.


   2 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

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check



checkCIF publication errors


Alert level A
PUBL010_ALERT_1_A  _publ_author_address is missing. Author(s) address(es).
PUBL018_ALERT_1_A The author field is longer than 65 characters.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL019_ALERT_1_A The author field is longer than 8 words.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL018_ALERT_1_A The author field is longer than 65 characters.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL019_ALERT_1_A The author field is longer than 8 words.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL018_ALERT_1_A The author field is longer than 65 characters.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL019_ALERT_1_A The author field is longer than 8 words.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL018_ALERT_1_A The author field is longer than 65 characters.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL019_ALERT_1_A The author field is longer than 8 words.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL018_ALERT_1_A The author field is longer than 65 characters.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL019_ALERT_1_A The author field is longer than 8 words.
              Please check that the author/address loop has been
              completed according to the CIF specification.
              Author = College of Chemistry & Chemical Engineering JingGangShan University 343009 Ji'an, JiangXi People's Republic of China
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.


  12 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing
Comment top

4-aminoantipyrine and its derivatives are important compounds in pharmacology and biochemistry. They are especially used as anti-inflammatory drugs (Hökelek et al., 2002). The structural chemistry of organotin carboxylate complexs has attracted considerable attention, owing to their good antitumor activities (Barbieri et al., 2001; Zhou et al., 2005), their versatile molecular structures and the supramolecular architectures exhibited by these complexes (Ma et al., 2005). In the context of our continued interest in the structural and biological properties of organotin complexes (Fang et al., 2001; Fang, et al., 2006), we have been interested in studying the biologigal properties of the title compound.

The title compound (E)-4-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl] benzoato-triphenyltin (IV), is a four-coordinate SnIV complex, with a distorted tetrahedron geometry (Fig. 1). The (E)-4-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl) benzoate ligand, coordinates in monodentate mode bonding with the triphenyltin group. The Sn1—O1 bond length is 2.044 (2) Å, which is slightly shorter than the value of 2.121 (3)Å reported by Fang, Sui et al. (2006a). The double bond C═ N length is 1.271 (3) Å, and this is comparable to the analogue of 1.280 (3)Å found by Hu et al. (2006).

The ring of pyrazole is well coplanar, with a mean deviation from the plane of 0.027 (3) Å, and makes an angle of 49.9 (2)° with the substituent phenyl (C1 to C6) and 20.7 (2)° with the benzene ring of 4-formylbenzoic acid (C13 to C18).

In the crystal lattice (Fig. 2), a weak aromatic π-π stacking interaction can be found between the pyrazole ring (Cg1) and benzene ring (Cg2) of 4-formylbenzoic acid [the distance of Cg1···Cg2i is 3.858 (2) Å; and the C10···C18i distance in the offset face-to-face interaction is 3.375 (4) Å; symmetry code: (i) 1 - x, 1 - y, -z)].

Related literature top

For related literature, see: Barbieri et al. (2001); Fang et al. (2001); Fang, Sui, Ying, Xu & Guo (2006); Fang, Xu, Guo & Zeng (2006); Hökelek et al. (2002); Ma et al. (2005); Zhou et al. (2005).

Experimental top

The title compound (I) was prepared by the following procedure: A solution of Schiff base ligand, (E)-4-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl)\ benzoic acid, (0.335 g, 1 m mol) and triphenyltin hydroxide (0.367 g, 1 mmol) in 20 ml mixed solvent (benzene:toluene = 1:1) was heated for 6 h under reflux. The solvent was removed by vacuum distillation in a rotary evaporator and a yellow solid product was obtained (yield 83%, m.p. 497–498 K). When the solid was recrystallized from toluene, single crystals suitable for X-ray diffraction analysis precipitated after several days.

Refinement top

One phenyl ring of the triphenyltin is disordered in the crystal structure. Each of the six atoms can be splitted into two parts to form two six-membered rings, and the positional occupancy factors is 0.54. A l l the H atoms were positioned in idealized locations and refined as riding on their carrier atoms, with C—H distances of 0.93 (aryl) and 0.96Å (methyl) with Uiso(H) = 1.5Ueq(C) for methyl and Uiso(H) = 1.2Ueq(C) for aryl.

Structure description top

4-aminoantipyrine and its derivatives are important compounds in pharmacology and biochemistry. They are especially used as anti-inflammatory drugs (Hökelek et al., 2002). The structural chemistry of organotin carboxylate complexs has attracted considerable attention, owing to their good antitumor activities (Barbieri et al., 2001; Zhou et al., 2005), their versatile molecular structures and the supramolecular architectures exhibited by these complexes (Ma et al., 2005). In the context of our continued interest in the structural and biological properties of organotin complexes (Fang et al., 2001; Fang, et al., 2006), we have been interested in studying the biologigal properties of the title compound.

The title compound (E)-4-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl] benzoato-triphenyltin (IV), is a four-coordinate SnIV complex, with a distorted tetrahedron geometry (Fig. 1). The (E)-4-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl) benzoate ligand, coordinates in monodentate mode bonding with the triphenyltin group. The Sn1—O1 bond length is 2.044 (2) Å, which is slightly shorter than the value of 2.121 (3)Å reported by Fang, Sui et al. (2006a). The double bond C═ N length is 1.271 (3) Å, and this is comparable to the analogue of 1.280 (3)Å found by Hu et al. (2006).

The ring of pyrazole is well coplanar, with a mean deviation from the plane of 0.027 (3) Å, and makes an angle of 49.9 (2)° with the substituent phenyl (C1 to C6) and 20.7 (2)° with the benzene ring of 4-formylbenzoic acid (C13 to C18).

In the crystal lattice (Fig. 2), a weak aromatic π-π stacking interaction can be found between the pyrazole ring (Cg1) and benzene ring (Cg2) of 4-formylbenzoic acid [the distance of Cg1···Cg2i is 3.858 (2) Å; and the C10···C18i distance in the offset face-to-face interaction is 3.375 (4) Å; symmetry code: (i) 1 - x, 1 - y, -z)].

For related literature, see: Barbieri et al. (2001); Fang et al. (2001); Fang, Sui, Ying, Xu & Guo (2006); Fang, Xu, Guo & Zeng (2006); Hökelek et al. (2002); Ma et al. (2005); Zhou et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: APEX2; software used to prepare material for publication: APEX2 and publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing 30% probability displacement ellipsoids. All the H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The packing diagram of (I), viewed down the a axis. All the H atoms and part of the disordered phenyl have been omitted for clarity.
{(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]\ benzoato}triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C19H16N3O3)]Z = 2
Mr = 684.34F(000) = 696
Triclinic, P1Dx = 1.408 Mg m−3
Hall symbol: -P 1Melting point = 497–498 K
a = 9.2009 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6299 (19) ÅCell parameters from 5058 reflections
c = 15.598 (2) Åθ = 2.4–29.2°
α = 74.435 (2)°µ = 0.83 mm−1
β = 77.913 (2)°T = 296 K
γ = 68.677 (2)°Block, yellow
V = 1613.9 (4) Å30.41 × 0.39 × 0.31 mm
Data collection top
Bruker APEX II area-detector
diffractometer		5246 independent reflections
Radiation source: fine-focus sealed tube5039 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −10→10
Tmin = 0.727, Tmax = 0.783k = −15→14
9137 measured reflectionsl = −18→18
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0309P)2 + 0.6678P]
where P = (Fo2 + 2Fc2)/3
5246 reflections(Δ/σ)max = 0.002
388 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
[Sn(C6H5)3(C19H16N3O3)]γ = 68.677 (2)°
Mr = 684.34V = 1613.9 (4) Å3
Triclinic, P1Z = 2
a = 9.2009 (14) ÅMo Kα radiation
b = 12.6299 (19) ŵ = 0.83 mm−1
c = 15.598 (2) ÅT = 296 K
α = 74.435 (2)°0.41 × 0.39 × 0.31 mm
β = 77.913 (2)°
Data collection top
Bruker APEX II area-detector
diffractometer		5246 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		5039 reflections with I > 2σ(I)
Tmin = 0.727, Tmax = 0.783Rint = 0.011
9137 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.060H-atom parameters constrained
S = 1.04Δρmax = 0.37 e Å−3
5246 reflectionsΔρmin = −0.27 e Å−3
388 parameters
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*/UeqOcc. (<1)
C320.5054 (2)0.77153 (16)0.45208 (11)0.0465 (6)0.536 (3)
C330.5808 (2)0.75898 (14)0.52445 (12)0.0605 (9)0.536 (3)
H330.62720.81320.52460.073*0.536 (3)
C340.5868 (3)0.66540 (18)0.59664 (11)0.0714 (13)0.536 (3)
H340.63720.65700.64510.086*0.536 (3)
C350.5174 (3)0.58438 (18)0.59645 (17)0.0784 (16)0.536 (3)
H350.52140.52180.64480.094*0.536 (3)
C360.4420 (4)0.5969 (2)0.5241 (2)0.0808 (13)0.536 (3)
H360.39560.54270.52400.097*0.536 (3)
C370.4360 (3)0.6905 (2)0.45190 (17)0.0650 (10)0.536 (3)
H370.38560.69890.40350.078*0.536 (3)
C32A0.5064 (2)0.78462 (14)0.46971 (11)0.0465 (6)0.464 (3)
C33A0.6317 (3)0.75826 (18)0.51712 (14)0.0605 (9)0.464 (3)
H33A0.70720.79520.49660.073*0.464 (3)
C34A0.6397 (3)0.6752 (2)0.59586 (13)0.0714 (13)0.464 (3)
H34A0.72500.65170.62760.086*0.464 (3)
C35A0.5229 (3)0.6275 (2)0.62702 (12)0.0784 (16)0.464 (3)
H35A0.52950.57110.67980.094*0.464 (3)
C36A0.3992 (3)0.6606 (2)0.58286 (17)0.0808 (13)0.464 (3)
H36A0.31790.62990.60640.097*0.464 (3)
C37A0.39118 (18)0.7403 (2)0.50232 (16)0.0650 (10)0.464 (3)
H37A0.30530.76270.47120.078*0.464 (3)
C10.1119 (2)0.41572 (17)−0.22321 (13)0.0423 (4)
C20.2001 (3)0.4252 (2)−0.30692 (14)0.0501 (5)
H20.30110.4287−0.31300.060*
C30.1371 (3)0.4295 (2)−0.38092 (15)0.0584 (6)
H30.19510.4378−0.43740.070*
C4−0.0104 (3)0.4217 (2)−0.37211 (16)0.0655 (7)
H4−0.05170.4234−0.42220.079*
C5−0.0974 (3)0.4114 (2)−0.28821 (17)0.0633 (6)
H5−0.19710.4055−0.28200.076*
C6−0.0374 (3)0.4097 (2)−0.21355 (15)0.0512 (5)
H6−0.09700.4047−0.15750.061*
C70.1644 (3)0.2264 (2)−0.05646 (17)0.0622 (6)
H7A0.26910.1866−0.08080.093*
H7B0.08990.2224−0.08940.093*
H7C0.14550.19030.00550.093*
C80.1921 (4)0.3250 (2)0.09253 (16)0.0676 (7)
H8A0.09270.31310.11560.101*
H8B0.21050.37090.12670.101*
H8C0.27430.25110.09710.101*
C90.1902 (3)0.38690 (19)−0.00328 (14)0.0471 (5)
C100.2312 (2)0.48386 (19)−0.04414 (13)0.0444 (5)
C110.2225 (3)0.50515 (19)−0.13904 (14)0.0467 (5)
C120.3037 (3)0.6390 (2)−0.03608 (15)0.0546 (5)
H120.30230.6662−0.09760.066*
C130.3429 (3)0.7033 (2)0.01676 (15)0.0511 (5)
C140.3378 (4)0.8184 (2)−0.01735 (17)0.0685 (7)
H140.31690.8535−0.07600.082*
C150.3635 (3)0.8807 (2)0.03530 (17)0.0665 (7)
H150.35820.95780.01200.080*
C160.3970 (3)0.8293 (2)0.12243 (14)0.0487 (5)
C170.4097 (3)0.7134 (2)0.15472 (15)0.0503 (5)
H170.43630.67720.21230.060*
C180.3834 (3)0.6508 (2)0.10266 (15)0.0503 (5)
H180.39290.57290.12540.060*
C190.4175 (3)0.8982 (2)0.18055 (15)0.0540 (6)
C200.6833 (3)0.97250 (19)0.29455 (14)0.0477 (5)
C210.6816 (3)1.0830 (2)0.29179 (17)0.0617 (6)
H210.58931.13710.31160.074*
C220.8154 (4)1.1144 (3)0.2600 (2)0.0774 (8)
H220.81321.18890.25900.093*
C230.9509 (4)1.0356 (3)0.2300 (2)0.0861 (9)
H231.04091.05650.20850.103*
C240.9544 (4)0.9259 (3)0.2316 (3)0.0909 (10)
H241.04650.87260.21070.109*
C250.8211 (3)0.8941 (2)0.2643 (2)0.0686 (7)
H250.82440.81920.26590.082*
C260.2702 (3)1.0560 (2)0.37759 (14)0.0498 (5)
C270.1939 (3)1.0432 (2)0.46467 (17)0.0641 (6)
H270.23240.97520.50660.077*
C280.0620 (4)1.1302 (3)0.4896 (2)0.0955 (11)
H280.01061.12090.54780.115*
C290.0069 (5)1.2307 (3)0.4277 (3)0.1140 (14)
H29−0.08141.29000.44470.137*
C300.0794 (5)1.2453 (3)0.3415 (3)0.1008 (11)
H300.04011.31360.30010.121*
C310.2119 (3)1.1576 (2)0.31647 (18)0.0697 (7)
H310.26191.16730.25800.084*
N10.2718 (2)0.54639 (17)0.00252 (12)0.0485 (4)
N20.1793 (2)0.41422 (16)−0.14869 (11)0.0467 (4)
N30.1472 (2)0.34757 (15)−0.06359 (11)0.0466 (4)
O10.4520 (2)0.83730 (15)0.26047 (11)0.0618 (4)
O20.4028 (3)1.00110 (17)0.15681 (13)0.0770 (5)
O30.2441 (2)0.58297 (16)−0.20178 (11)0.0671 (5)
Sn10.480454 (17)0.922187 (12)0.347192 (9)0.04610 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C320.0509 (13)0.0475 (15)0.0381 (14)−0.0128 (11)−0.0024 (10)−0.0110 (11)
C330.078 (3)0.0494 (16)0.0603 (16)−0.0201 (16)−0.0200 (17)−0.0135 (13)
C340.086 (3)0.064 (2)0.0606 (18)−0.010 (2)−0.0268 (19)−0.0137 (15)
C350.084 (3)0.063 (3)0.073 (3)−0.024 (2)−0.013 (2)0.013 (2)
C360.080 (3)0.069 (3)0.094 (3)−0.046 (2)−0.015 (2)0.014 (2)
C370.062 (2)0.069 (3)0.066 (3)−0.034 (2)−0.0151 (19)0.0047 (17)
C32A0.0509 (13)0.0475 (15)0.0381 (14)−0.0128 (11)−0.0024 (10)−0.0110 (11)
C33A0.078 (3)0.0494 (16)0.0603 (16)−0.0201 (16)−0.0200 (17)−0.0135 (13)
C34A0.086 (3)0.064 (2)0.0606 (18)−0.010 (2)−0.0268 (19)−0.0137 (15)
C35A0.084 (3)0.063 (3)0.073 (3)−0.024 (2)−0.013 (2)0.013 (2)
C36A0.080 (3)0.069 (3)0.094 (3)−0.046 (2)−0.015 (2)0.014 (2)
C37A0.062 (2)0.069 (3)0.066 (3)−0.034 (2)−0.0151 (19)0.0047 (17)
C10.0539 (12)0.0341 (11)0.0399 (10)−0.0141 (9)−0.0064 (8)−0.0091 (8)
C20.0547 (12)0.0479 (13)0.0464 (12)−0.0179 (10)−0.0017 (9)−0.0096 (10)
C30.0740 (16)0.0575 (15)0.0398 (11)−0.0196 (12)−0.0017 (10)−0.0108 (10)
C40.0819 (18)0.0727 (18)0.0473 (13)−0.0246 (14)−0.0194 (12)−0.0137 (12)
C50.0586 (14)0.0754 (18)0.0614 (15)−0.0252 (13)−0.0145 (11)−0.0133 (13)
C60.0535 (12)0.0548 (14)0.0445 (11)−0.0184 (10)0.0000 (9)−0.0128 (10)
C70.0867 (18)0.0441 (14)0.0575 (14)−0.0269 (12)−0.0085 (12)−0.0063 (11)
C80.097 (2)0.0619 (17)0.0429 (12)−0.0285 (14)−0.0115 (12)−0.0043 (11)
C90.0529 (12)0.0458 (13)0.0389 (10)−0.0128 (10)−0.0045 (9)−0.0086 (9)
C100.0465 (11)0.0453 (12)0.0418 (11)−0.0138 (9)−0.0041 (8)−0.0123 (9)
C110.0553 (12)0.0453 (13)0.0443 (11)−0.0217 (10)−0.0055 (9)−0.0104 (10)
C120.0660 (14)0.0589 (15)0.0458 (12)−0.0255 (12)−0.0063 (10)−0.0155 (11)
C130.0546 (12)0.0557 (14)0.0498 (12)−0.0232 (11)−0.0011 (9)−0.0188 (10)
C140.105 (2)0.0661 (17)0.0467 (13)−0.0423 (15)−0.0147 (13)−0.0075 (12)
C150.098 (2)0.0545 (15)0.0580 (14)−0.0390 (14)−0.0117 (13)−0.0087 (12)
C160.0505 (12)0.0531 (14)0.0484 (12)−0.0216 (10)−0.0002 (9)−0.0181 (10)
C170.0507 (12)0.0549 (14)0.0496 (12)−0.0182 (10)−0.0080 (9)−0.0152 (10)
C180.0507 (12)0.0480 (13)0.0562 (13)−0.0178 (10)−0.0076 (10)−0.0146 (10)
C190.0579 (13)0.0596 (16)0.0527 (13)−0.0262 (11)0.0015 (10)−0.0215 (11)
C200.0576 (13)0.0477 (13)0.0417 (11)−0.0233 (10)−0.0057 (9)−0.0077 (9)
C210.0731 (16)0.0491 (14)0.0647 (15)−0.0231 (12)−0.0063 (12)−0.0123 (11)
C220.100 (2)0.0607 (18)0.086 (2)−0.0478 (17)−0.0129 (16)−0.0063 (15)
C230.0746 (19)0.095 (2)0.098 (2)−0.0501 (19)0.0008 (16)−0.0129 (19)
C240.0642 (18)0.083 (2)0.122 (3)−0.0289 (16)0.0144 (17)−0.031 (2)
C250.0681 (16)0.0535 (16)0.0856 (18)−0.0238 (13)0.0043 (13)−0.0218 (13)
C260.0600 (13)0.0457 (13)0.0468 (12)−0.0193 (10)−0.0061 (10)−0.0125 (10)
C270.0788 (17)0.0548 (15)0.0576 (14)−0.0278 (13)0.0038 (12)−0.0113 (12)
C280.105 (2)0.076 (2)0.088 (2)−0.0301 (19)0.0373 (19)−0.0272 (18)
C290.100 (3)0.070 (2)0.131 (3)0.0009 (19)0.029 (2)−0.027 (2)
C300.110 (3)0.058 (2)0.098 (3)0.0032 (18)−0.008 (2)−0.0051 (17)
C310.0848 (18)0.0567 (16)0.0538 (14)−0.0108 (14)−0.0067 (12)−0.0081 (12)
N10.0516 (10)0.0518 (11)0.0460 (10)−0.0171 (9)−0.0046 (8)−0.0176 (8)
N20.0629 (11)0.0457 (11)0.0360 (9)−0.0258 (9)−0.0069 (7)−0.0041 (7)
N30.0629 (11)0.0388 (10)0.0386 (9)−0.0204 (8)−0.0059 (8)−0.0041 (7)
O10.0841 (12)0.0599 (11)0.0540 (9)−0.0310 (9)−0.0121 (8)−0.0193 (8)
O20.1188 (16)0.0598 (12)0.0684 (11)−0.0432 (11)−0.0131 (11)−0.0185 (9)
O30.1088 (14)0.0638 (11)0.0454 (9)−0.0542 (10)−0.0106 (9)−0.0012 (8)
Sn10.05547 (10)0.04475 (10)0.04128 (9)−0.02024 (7)−0.00573 (6)−0.00908 (6)
Geometric parameters (Å, º) top
C32—C331.3900C10—N11.389 (3)
C32—C371.3900C10—C111.446 (3)
C32—Sn12.126 (2)C11—O31.228 (3)
C33—C341.3900C11—N21.396 (3)
C33—H330.93C12—N11.271 (3)
C34—C351.3900C12—C131.471 (3)
C34—H340.93C12—H120.93
C35—C361.3900C13—C181.388 (3)
C35—H350.93C13—C141.394 (4)
C36—C371.3900C14—C151.384 (4)
C36—H360.93C14—H140.93
C37—H370.93C15—C161.386 (3)
C32A—C37A1.3224C15—H150.93
C32A—C33A1.3900C16—C171.384 (3)
C32A—Sn12.199 (2)C16—C191.493 (3)
C33A—C34A1.3802C17—C181.382 (3)
C33A—H33A0.93C17—H170.93
C34A—C35A1.3592C18—H180.93
C34A—H34A0.93C19—O21.216 (3)
C35A—C36A1.3313C19—O11.311 (3)
C35A—H35A0.93C20—C251.377 (3)
C36A—C37A1.3792C20—C211.379 (3)
C36A—H36A0.93C20—Sn12.122 (2)
C37A—H37A0.93C21—C221.382 (4)
C1—C61.377 (3)C21—H210.9300
C1—C21.386 (3)C22—C231.366 (5)
C1—N21.421 (3)C22—H220.93
C2—C31.376 (3)C23—C241.367 (5)
C2—H20.93C23—H230.93
C3—C41.372 (4)C24—C251.382 (4)
C3—H30.93C24—H240.93
C4—C51.384 (4)C25—H250.93
C4—H40.93C26—C311.379 (3)
C5—C61.382 (3)C26—C271.389 (3)
C5—H50.93C26—Sn12.119 (2)
C6—H60.93C27—C281.376 (4)
C7—N31.456 (3)C27—H270.93
C7—H7A0.96C28—C291.370 (5)
C7—H7B0.96C28—H280.93
C7—H7C0.96C29—C301.367 (5)
C8—C91.490 (3)C29—H290.93
C8—H8A0.96C30—C311.384 (4)
C8—H8B0.96C30—H300.93
C8—H8C0.96C31—H310.93
C9—N31.356 (3)N2—N31.405 (2)
C9—C101.366 (3)O1—Sn12.044 (2)
C33—C32—C37120.0C13—C12—H12120.0
C33—C32—Sn1119.62 (10)C18—C13—C14118.5 (2)
C37—C32—Sn1120.19 (10)C18—C13—C12120.4 (2)
C32—C33—C34120.0C14—C13—C12121.1 (2)
C32—C33—H33120.0C15—C14—C13120.6 (2)
C34—C33—H33120.0C15—C14—H14119.7
C33—C34—C35120.0C13—C14—H14119.7
C33—C34—H34120.0C14—C15—C16120.6 (2)
C35—C34—H34120.0C14—C15—H15119.7
C34—C35—C36120.0C16—C15—H15119.7
C34—C35—H35120.0C17—C16—C15118.8 (2)
C36—C35—H35120.0C17—C16—C19120.7 (2)
C37—C36—C35120.0C15—C16—C19120.5 (2)
C37—C36—H36120.0C18—C17—C16120.9 (2)
C35—C36—H36120.0C18—C17—H17119.5
C36—C37—C32120.0C16—C17—H17119.5
C36—C37—H37120.0C17—C18—C13120.5 (2)
C32—C37—H37120.0C17—C18—H18119.7
C37A—C32A—C33A121.6C13—C18—H18119.7
C37A—C32A—Sn1118.54 (10)O2—C19—O1122.9 (2)
C33A—C32A—Sn1119.23 (10)O2—C19—C16123.6 (2)
C34A—C33A—C32A117.4O1—C19—C16113.5 (2)
C34A—C33A—H33A121.3C25—C20—C21118.5 (2)
C32A—C33A—H33A121.3C25—C20—Sn1120.44 (18)
C35A—C34A—C33A120.1C21—C20—Sn1121.00 (18)
C35A—C34A—H34A120.0C20—C21—C22120.8 (3)
C33A—C34A—H34A120.0C20—C21—H21119.6
C36A—C35A—C34A120.8C22—C21—H21119.6
C36A—C35A—H35A119.6C23—C22—C21119.8 (3)
C34A—C35A—H35A119.6C23—C22—H22120.1
C35A—C36A—C37A120.3C21—C22—H22120.1
C35A—C36A—H36A119.9C22—C23—C24120.2 (3)
C37A—C36A—H36A119.9C22—C23—H23119.9
C32A—C37A—C36A119.6C24—C23—H23119.9
C32A—C37A—H37A120.2C23—C24—C25120.0 (3)
C36A—C37A—H37A120.2C23—C24—H24120.0
C6—C1—C2120.57 (19)C25—C24—H24120.0
C6—C1—N2121.49 (18)C20—C25—C24120.6 (3)
C2—C1—N2117.93 (19)C20—C25—H25119.7
C3—C2—C1119.5 (2)C24—C25—H25119.7
C3—C2—H2120.2C31—C26—C27118.9 (2)
C1—C2—H2120.2C31—C26—Sn1122.89 (18)
C4—C3—C2120.6 (2)C27—C26—Sn1118.11 (18)
C4—C3—H3119.7C28—C27—C26120.7 (3)
C2—C3—H3119.7C28—C27—H27119.7
C3—C4—C5119.6 (2)C26—C27—H27119.7
C3—C4—H4120.2C29—C28—C27119.3 (3)
C5—C4—H4120.2C29—C28—H28120.3
C6—C5—C4120.5 (2)C27—C28—H28120.3
C6—C5—H5119.7C30—C29—C28121.2 (3)
C4—C5—H5119.7C30—C29—H29119.4
C1—C6—C5119.2 (2)C28—C29—H29119.4
C1—C6—H6120.4C29—C30—C31119.4 (3)
C5—C6—H6120.4C29—C30—H30120.3
N3—C7—H7A109.5C31—C30—H30120.3
N3—C7—H7B109.5C26—C31—C30120.5 (3)
H7A—C7—H7B109.5C26—C31—H31119.7
N3—C7—H7C109.5C30—C31—H31119.7
H7A—C7—H7C109.5C12—N1—C10122.07 (19)
H7B—C7—H7C109.5C11—N2—N3109.44 (16)
C9—C8—H8A109.5C11—N2—C1124.73 (17)
C9—C8—H8B109.5N3—N2—C1120.68 (16)
H8A—C8—H8B109.5C9—N3—N2106.94 (16)
C9—C8—H8C109.5C9—N3—C7124.42 (18)
H8A—C8—H8C109.5N2—N3—C7118.36 (17)
H8B—C8—H8C109.5C19—O1—Sn1117.4 (2)
N3—C9—C10110.51 (18)O1—Sn1—C26111.39 (8)
N3—C9—C8121.1 (2)O1—Sn1—C20107.81 (8)
C10—C9—C8128.3 (2)C26—Sn1—C20116.41 (9)
C9—C10—N1122.92 (19)O1—Sn1—C3291.00 (8)
C9—C10—C11107.82 (18)C26—Sn1—C32110.05 (8)
N1—C10—C11129.26 (19)C20—Sn1—C32117.23 (8)
O3—C11—N2123.60 (19)O1—Sn1—C32A100.30 (7)
O3—C11—C10131.7 (2)C26—Sn1—C32A105.28 (8)
N2—C11—C10104.70 (17)C20—Sn1—C32A114.52 (8)
N1—C12—C13119.9 (2)C32—Sn1—C32A9.4
N1—C12—H12120.0

Experimental details

Crystal data
Chemical formula[Sn(C6H5)3(C19H16N3O3)]
Mr684.34
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.2009 (14), 12.6299 (19), 15.598 (2)
α, β, γ (°)74.435 (2), 77.913 (2), 68.677 (2)
V (Å3)1613.9 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.83
Crystal size (mm)0.41 × 0.39 × 0.31
Data collection
DiffractometerBruker APEX II area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.727, 0.783
No. of measured, independent and
observed [I > 2σ(I)] reflections		9137, 5246, 5039
Rint0.011
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.060, 1.04
No. of reflections5246
No. of parameters388
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.27

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), APEX2 and publCIF (Westrip, 2007).

Selected geometric parameters (Å, º) top
C32—Sn12.126 (2)C19—O11.311 (3)
C32A—Sn12.199 (2)C20—Sn12.122 (2)
C11—O31.228 (3)C26—Sn12.119 (2)
C12—N11.271 (3)O1—Sn12.044 (2)
C19—O21.216 (3)
O2—C19—O1122.9 (2)C26—Sn1—C20116.41 (9)
C19—O1—Sn1117.4 (2)O1—Sn1—C3291.00 (8)
O1—Sn1—C26111.39 (8)C26—Sn1—C32110.05 (8)
O1—Sn1—C20107.81 (8)C20—Sn1—C32117.23 (8)
 

Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS