metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Pages m561-m562

(2-Amino-3-nitro­benzoato-κO)tri­phenyl­tin(IV)

aDepartment of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, 31900 Kampar, Perak, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 29 March 2011; accepted 4 April 2011; online 13 April 2011)

The asymmetric unit of the title compound, [Sn(C6H5)3(C7H5N2O4)], consists of two independent mol­ecules. In each mol­ecule, the four-coordinated SnIV atom exists in a distorted tetra­hedral geometry and two intra­molecular N—H⋯O hydrogen bonds with S(6) ring motifs are present. In one mol­ecule, the benzene ring of the 2-amino-3-nitro­benzoate ligand makes dihedral angles of 42.74 (11), 89.66 (13) and 53.04 (10)° with the three phenyl rings. The corresponding dihedral angles for the other mol­ecule are 6.29 (11), 66.55 (11) and 62.33 (10)°. In the crystal, a weak inter­molecular C—H⋯π inter­action and a ππ stacking inter­action with a centroid–centroid distance of 3.5877 (12) Å are observed.

Related literature

For general background to and the coordination environment of the title complex, see: Yeap & Teoh (2003[Yeap, L.-L. & Teoh, S.-G. (2003). J. Coord. Chem. 56, 701-708.]); Win et al. (2007[Win, Y. F., Teoh, S.-G., Zakaria, L., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, m348-m350.], 2008[Win, Y. F., Teoh, S. G., Ha, S. T., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, m1530-m1531.], 2010[Win, Y. F., Teoh, S. G., Vikneswaran, M. R., Goh, J. H. & Fun, H.-K. (2010). Acta Cryst. E66, m695-m696.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H5)3(C7H5N2O4)]

  • Mr = 531.12

  • Triclinic, [P \overline 1]

  • a = 11.2836 (1) Å

  • b = 14.9600 (2) Å

  • c = 15.1828 (3) Å

  • α = 109.257 (1)°

  • β = 98.503 (1)°

  • γ = 105.743 (1)°

  • V = 2247.89 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.17 mm−1

  • T = 296 K

  • 0.44 × 0.32 × 0.19 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.628, Tmax = 0.810

  • 69259 measured reflections

  • 18711 independent reflections

  • 12707 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.080

  • S = 1.01

  • 18711 reflections

  • 593 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.70 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1A–C6A phenyl ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1NA⋯O3A 0.84 (3) 2.02 (3) 2.632 (3) 129 (2)
N1A—H2NA⋯O2A 0.84 (3) 1.99 (3) 2.671 (3) 138 (2)
N1B—H1NB⋯O2B 0.84 (2) 1.98 (3) 2.643 (3) 135 (2)
N1B—H2NB⋯O3B 0.83 (2) 1.96 (2) 2.607 (3) 135.3 (19)
C15B—H15BCg1i 0.93 2.84 3.596 (3) 139
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Commonly, triphenyltin(IV) carboxylate complexes exist as a monomeric and polymeric structures (Yeap &Teoh, 2003; Win et al., 2007, 2008, 2010). For monomeric structures, the tin(IV) moiety could be either four- or five-coordinated. However, for polymeric structures, the tin(IV) moiety normally exist in five-coordinated (Win et al., 2010). The title complex is found to be similar to the reported structure of (2-amino-5-nitrobenzoato)triphenyltin(IV) (Win et al., 2007) with the exception that the nitro group is in a different position at the benzoate moiety in this study.

The asymmetric unit contains two independent molecules (Fig. 1), A and B. In each molecule, the four-coordinate tin atom (Sn1A/Sn1B) exists in a distorted tetrahedral geometry, formed by a monodentate carboxylate group and three phenyl rings. The molecular structure is stabilized by intramolecular N1A—H1NA···O3A, N1A—H2NA···O2A, N1B—H1NB···O2B and N1B—H2NB···O3B hydrogen bonds (Table 1) which generate S(6) ring motifs (Fig. 1; Bernstein et al., 1995). Bond lengths (Allen et al., 1987) and angles are within normal ranges. In molecule A, the phenyl ring (C20A–C25A) of 2-amino-3-nitrobenzoate moiety makes dihedral angles of 42.74 (11), 89.66 (13) and 53.04 (10)° with respect to the three phenyl rings (C1A–C6A, C7A–C12A and C13A–C18A). The corresponding dihedral angles for molecule B are 6.29 (11), 66.55 (11) and 62.33 (10)°.

In the crystal (Fig. 2), a weak intermolecular C—H···π interaction (Table 1) and a ππ stacking interaction between two phenyl rings (C20B–C25B, centroid Cg2), with a Cg2···Cg2 distance of 3.5877 (12) Å are observed. No significant intermolecular hydrogen bond is observed.

Related literature top

For general background to and the coordination environment of the title complex, see: Yeap & Teoh (2003); Win et al. (2007, 2008, 2010). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title complex was obtained by heating under reflux a 1:1 molar mixture of triphenyltin(IV) hydroxide (0.73 g, 2 mmol) and 2-amino-3-nitrobenzoic acid (0.36 g, 2 mmol) in methanol (60 mL) for 2 h. A clear yellow transparent solution was separated by filtration and kept in a bottle. After a few days, yellow crystals (0.46 g, 86.0 % yield) were collected (m.p. 155.0–156.0 °C). Analysis for C25H20N2O4Sn: C 56.72, H 3.73, N 5.24%. Calculated for C25H20N2O4Sn: C 56.53, H 3.80, N, 5.27%.

Refinement top

H1NA, H2NA, H1NB and H2NB were located in a difference Fourier map and allowed to refined freely. The remaining H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The highest residual electron density peak is located at 0.60 Å from H22A and the deepest hole is located at 0.64 Å from Sn1A.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 20% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed along the a axis.
(2-Amino-3-nitrobenzoato-κO)triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C7H5N2O4)]Z = 4
Mr = 531.12F(000) = 1064
Triclinic, P1Dx = 1.569 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.2836 (1) ÅCell parameters from 9889 reflections
b = 14.9600 (2) Åθ = 2.5–30.3°
c = 15.1828 (3) ŵ = 1.17 mm1
α = 109.257 (1)°T = 296 K
β = 98.503 (1)°Block, yellow
γ = 105.743 (1)°0.44 × 0.32 × 0.19 mm
V = 2247.89 (6) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
18711 independent reflections
Radiation source: fine-focus sealed tube12707 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 34.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1717
Tmin = 0.628, Tmax = 0.810k = 2323
69259 measured reflectionsl = 2424
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0314P)2 + 0.4012P]
where P = (Fo2 + 2Fc2)/3
18711 reflections(Δ/σ)max = 0.003
593 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
[Sn(C6H5)3(C7H5N2O4)]γ = 105.743 (1)°
Mr = 531.12V = 2247.89 (6) Å3
Triclinic, P1Z = 4
a = 11.2836 (1) ÅMo Kα radiation
b = 14.9600 (2) ŵ = 1.17 mm1
c = 15.1828 (3) ÅT = 296 K
α = 109.257 (1)°0.44 × 0.32 × 0.19 mm
β = 98.503 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
18711 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
12707 reflections with I > 2σ(I)
Tmin = 0.628, Tmax = 0.810Rint = 0.027
69259 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.70 e Å3
18711 reflectionsΔρmin = 0.42 e Å3
593 parameters
Special details top

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. 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 > 2sigma(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
Sn1A0.345584 (12)0.684458 (9)0.766833 (10)0.05415 (4)
N1A0.5711 (2)0.41300 (17)0.82572 (15)0.0679 (5)
N2A0.52199 (18)0.26757 (13)0.91798 (13)0.0650 (4)
O1A0.33579 (15)0.58591 (11)0.83593 (12)0.0692 (4)
O2A0.49933 (15)0.55427 (12)0.78536 (12)0.0731 (4)
O3A0.60941 (19)0.26953 (15)0.87753 (15)0.0931 (6)
O4A0.49988 (17)0.21485 (14)0.96419 (14)0.0900 (5)
C1A0.09780 (18)0.73884 (14)0.75590 (15)0.0555 (4)
H1AA0.10460.73700.69510.067*
C2A0.0055 (2)0.75611 (17)0.78786 (18)0.0670 (5)
H2AA0.06850.76470.74780.080*
C3A0.0165 (2)0.76071 (17)0.87803 (18)0.0678 (5)
H3AA0.08640.77230.89890.081*
C4A0.0762 (2)0.74820 (16)0.93671 (16)0.0650 (5)
H4AA0.06980.75220.99820.078*
C5A0.1789 (2)0.72970 (15)0.90574 (15)0.0607 (5)
H5AA0.24080.72070.94640.073*
C6A0.19167 (16)0.72423 (13)0.81431 (14)0.0510 (4)
C7A0.30532 (19)0.59320 (14)0.61907 (15)0.0586 (5)
C8A0.3937 (3)0.6018 (2)0.5665 (2)0.0912 (8)
H8AA0.47550.64850.59730.109*
C9A0.3648 (3)0.5436 (3)0.4697 (2)0.1051 (10)
H9AA0.42720.55090.43640.126*
C10A0.2474 (3)0.4762 (2)0.4227 (2)0.0995 (9)
H10A0.22770.43850.35670.119*
C11A0.1570 (3)0.4635 (2)0.4728 (3)0.1121 (11)
H11A0.07640.41520.44130.135*
C12A0.1854 (2)0.5225 (2)0.5701 (2)0.0866 (7)
H12A0.12280.51440.60320.104*
C13A0.51909 (16)0.80878 (13)0.82951 (13)0.0480 (4)
C14A0.63718 (18)0.80336 (15)0.81823 (16)0.0600 (5)
H14A0.64470.74110.78670.072*
C15A0.74387 (19)0.88986 (17)0.85355 (17)0.0671 (5)
H15A0.82230.88580.84440.080*
C16A0.7335 (2)0.98195 (16)0.90228 (14)0.0627 (5)
H16A0.80551.03990.92700.075*
C17A0.6184 (2)0.98888 (15)0.91460 (13)0.0591 (5)
H17A0.61211.05130.94730.071*
C18A0.51119 (18)0.90262 (14)0.87819 (13)0.0520 (4)
H18A0.43290.90760.88650.062*
C19A0.4145 (2)0.53623 (14)0.82546 (15)0.0575 (4)
C20A0.39134 (18)0.45685 (12)0.86679 (13)0.0508 (4)
C21A0.2883 (2)0.44010 (15)0.90545 (15)0.0613 (5)
H21A0.23500.47760.90410.074*
C22A0.2616 (2)0.36870 (17)0.94646 (18)0.0712 (6)
H22A0.19070.35790.97120.085*
C23A0.3406 (2)0.31507 (16)0.94982 (16)0.0640 (5)
H23A0.32490.26860.97880.077*
C24A0.44437 (18)0.32867 (13)0.91065 (13)0.0528 (4)
C25A0.47379 (17)0.39891 (13)0.86597 (12)0.0495 (4)
Sn1B0.018573 (11)0.827628 (9)0.339100 (8)0.04415 (4)
N1B0.45431 (19)1.04371 (15)0.31356 (12)0.0643 (5)
N2B0.69475 (15)1.19985 (12)0.43518 (13)0.0582 (4)
O1B0.17982 (11)0.93658 (9)0.44468 (9)0.0506 (3)
O2B0.22688 (11)0.92890 (10)0.30778 (9)0.0547 (3)
O3B0.67725 (15)1.17694 (12)0.34679 (12)0.0733 (4)
O4B0.79777 (14)1.25610 (13)0.49218 (13)0.0851 (5)
C1B0.2120 (2)0.72477 (18)0.39784 (16)0.0722 (6)
H1BA0.24030.68510.33200.087*
C2B0.2892 (2)0.7087 (2)0.4578 (2)0.0926 (8)
H2BA0.36880.65810.43220.111*
C3B0.2494 (3)0.7666 (2)0.5542 (2)0.0815 (7)
H3BA0.30160.75560.59440.098*
C4B0.1336 (3)0.83997 (18)0.59140 (16)0.0728 (6)
H4BA0.10650.87970.65720.087*
C5B0.0555 (2)0.85649 (15)0.53250 (14)0.0596 (5)
H5BA0.02400.90720.55930.072*
C6B0.09302 (16)0.79919 (13)0.43473 (12)0.0462 (4)
C7B0.07386 (16)0.89100 (13)0.25507 (12)0.0465 (4)
C8B0.03269 (19)0.91179 (15)0.18003 (14)0.0569 (4)
H8BA0.04000.89940.16540.068*
C9B0.0984 (2)0.95064 (18)0.12670 (17)0.0717 (6)
H9BA0.06980.96430.07650.086*
C10B0.2058 (3)0.96913 (19)0.14761 (19)0.0804 (7)
H10B0.24950.99570.11200.097*
C11B0.2486 (2)0.9484 (2)0.22107 (18)0.0805 (7)
H11B0.32120.96110.23550.097*
C12B0.1834 (2)0.90832 (17)0.27374 (15)0.0629 (5)
H12B0.21400.89290.32250.076*
C13B0.05632 (15)0.69726 (13)0.25895 (12)0.0457 (3)
C14B0.02836 (19)0.61415 (15)0.28369 (15)0.0599 (5)
H14B0.00080.61740.33850.072*
C15B0.0436 (2)0.52591 (16)0.2271 (2)0.0773 (7)
H15B0.02490.47040.24430.093*
C16B0.0857 (2)0.52049 (17)0.1467 (2)0.0803 (7)
H16B0.09500.46100.10880.096*
C17B0.1141 (2)0.60122 (18)0.12143 (17)0.0755 (6)
H17B0.14240.59680.06620.091*
C18B0.1010 (2)0.68972 (15)0.17743 (14)0.0591 (5)
H18B0.12240.74510.16030.071*
C19B0.25866 (15)0.96723 (13)0.39734 (13)0.0452 (3)
C20B0.38243 (15)1.04711 (12)0.45527 (11)0.0406 (3)
C21B0.40676 (17)1.08618 (14)0.55438 (13)0.0503 (4)
H21B0.34541.06040.58270.060*
C22B0.5194 (2)1.16257 (15)0.61373 (13)0.0596 (5)
H22B0.53241.18850.68050.071*
C23B0.61088 (18)1.19894 (14)0.57229 (14)0.0550 (4)
H23B0.68701.24990.61110.066*
C24B0.59078 (15)1.16028 (12)0.47263 (13)0.0462 (4)
C25B0.47582 (15)1.08341 (12)0.40975 (12)0.0422 (3)
H1NA0.622 (2)0.382 (2)0.8298 (18)0.082 (8)*
H2NA0.584 (2)0.459 (2)0.8047 (18)0.080 (8)*
H1NB0.385 (2)0.9977 (18)0.2799 (16)0.066 (7)*
H2NB0.509 (2)1.0718 (16)0.2916 (15)0.063 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn1A0.04460 (7)0.04622 (7)0.07074 (9)0.01421 (5)0.01363 (6)0.02335 (6)
N1A0.0716 (12)0.0704 (12)0.0796 (13)0.0335 (10)0.0282 (10)0.0402 (11)
N2A0.0665 (11)0.0587 (10)0.0643 (10)0.0175 (8)0.0010 (8)0.0274 (9)
O1A0.0741 (9)0.0562 (8)0.0905 (11)0.0309 (7)0.0241 (8)0.0365 (8)
O2A0.0750 (10)0.0716 (10)0.0917 (11)0.0294 (8)0.0286 (9)0.0484 (9)
O3A0.1010 (14)0.1063 (14)0.1205 (15)0.0650 (12)0.0494 (12)0.0708 (13)
O4A0.0896 (12)0.0917 (12)0.1088 (13)0.0313 (10)0.0143 (10)0.0683 (11)
C1A0.0564 (11)0.0529 (10)0.0639 (11)0.0192 (8)0.0167 (9)0.0302 (9)
C2A0.0607 (12)0.0718 (13)0.0852 (15)0.0347 (11)0.0190 (11)0.0412 (12)
C3A0.0678 (13)0.0641 (13)0.0845 (15)0.0323 (11)0.0323 (12)0.0315 (12)
C4A0.0771 (14)0.0608 (12)0.0606 (12)0.0258 (11)0.0228 (10)0.0240 (10)
C5A0.0595 (11)0.0576 (11)0.0607 (11)0.0189 (9)0.0045 (9)0.0235 (9)
C6A0.0430 (9)0.0398 (8)0.0662 (11)0.0093 (7)0.0097 (8)0.0215 (8)
C7A0.0532 (10)0.0487 (10)0.0720 (12)0.0168 (8)0.0107 (9)0.0241 (9)
C8A0.0702 (15)0.0901 (19)0.0861 (18)0.0035 (13)0.0237 (13)0.0188 (15)
C9A0.105 (2)0.109 (2)0.089 (2)0.0229 (19)0.0405 (18)0.0291 (18)
C10A0.117 (3)0.093 (2)0.0711 (16)0.0404 (19)0.0080 (17)0.0138 (15)
C11A0.087 (2)0.094 (2)0.101 (2)0.0076 (17)0.0074 (18)0.0046 (18)
C12A0.0650 (14)0.0775 (16)0.0903 (18)0.0084 (12)0.0136 (13)0.0154 (14)
C13A0.0468 (9)0.0504 (9)0.0501 (9)0.0154 (7)0.0118 (7)0.0248 (8)
C14A0.0505 (10)0.0541 (10)0.0772 (13)0.0215 (8)0.0154 (9)0.0254 (10)
C15A0.0438 (10)0.0728 (14)0.0842 (15)0.0154 (9)0.0140 (10)0.0349 (12)
C16A0.0641 (12)0.0563 (11)0.0506 (10)0.0022 (9)0.0057 (9)0.0186 (9)
C17A0.0783 (13)0.0508 (10)0.0428 (9)0.0154 (9)0.0208 (9)0.0146 (8)
C18A0.0562 (10)0.0573 (10)0.0477 (9)0.0210 (8)0.0223 (8)0.0218 (8)
C19A0.0594 (11)0.0462 (9)0.0598 (11)0.0153 (8)0.0062 (9)0.0180 (9)
C20A0.0550 (10)0.0380 (8)0.0481 (9)0.0116 (7)0.0031 (7)0.0108 (7)
C21A0.0586 (11)0.0516 (10)0.0673 (12)0.0148 (9)0.0143 (9)0.0194 (9)
C22A0.0671 (13)0.0625 (12)0.0832 (15)0.0159 (10)0.0289 (12)0.0286 (12)
C23A0.0665 (13)0.0533 (11)0.0653 (12)0.0091 (9)0.0128 (10)0.0258 (10)
C24A0.0552 (10)0.0432 (9)0.0487 (9)0.0119 (8)0.0001 (8)0.0139 (7)
C25A0.0501 (9)0.0426 (8)0.0443 (8)0.0091 (7)0.0030 (7)0.0121 (7)
Sn1B0.04191 (6)0.04688 (6)0.04199 (6)0.01176 (5)0.01300 (4)0.01712 (5)
N1B0.0568 (10)0.0749 (12)0.0463 (8)0.0049 (9)0.0088 (8)0.0296 (9)
N2B0.0469 (8)0.0537 (9)0.0721 (11)0.0078 (7)0.0127 (8)0.0307 (8)
O1B0.0409 (6)0.0520 (7)0.0567 (7)0.0088 (5)0.0139 (5)0.0237 (6)
O2B0.0441 (6)0.0573 (7)0.0501 (7)0.0051 (5)0.0039 (5)0.0191 (6)
O3B0.0664 (9)0.0745 (10)0.0738 (10)0.0054 (7)0.0280 (8)0.0334 (8)
O4B0.0477 (8)0.0886 (12)0.0962 (12)0.0068 (8)0.0047 (8)0.0382 (10)
C1B0.0516 (11)0.0810 (15)0.0603 (12)0.0035 (10)0.0121 (9)0.0206 (11)
C2B0.0570 (13)0.106 (2)0.110 (2)0.0019 (13)0.0320 (14)0.0519 (18)
C3B0.0943 (18)0.0956 (18)0.0986 (19)0.0467 (15)0.0634 (16)0.0639 (16)
C4B0.1108 (19)0.0692 (14)0.0558 (11)0.0375 (14)0.0408 (12)0.0323 (11)
C5B0.0695 (12)0.0515 (10)0.0490 (10)0.0098 (9)0.0152 (9)0.0177 (8)
C6B0.0458 (9)0.0463 (8)0.0452 (8)0.0118 (7)0.0145 (7)0.0184 (7)
C7B0.0457 (9)0.0436 (8)0.0424 (8)0.0122 (7)0.0069 (7)0.0117 (7)
C8B0.0510 (10)0.0642 (12)0.0590 (11)0.0178 (9)0.0134 (8)0.0302 (10)
C9B0.0705 (14)0.0792 (15)0.0685 (13)0.0192 (12)0.0091 (11)0.0418 (12)
C10B0.0841 (16)0.0780 (15)0.0809 (16)0.0365 (13)0.0002 (13)0.0353 (13)
C11B0.0751 (15)0.0960 (18)0.0774 (15)0.0518 (14)0.0147 (12)0.0265 (14)
C12B0.0605 (12)0.0768 (14)0.0538 (10)0.0327 (10)0.0177 (9)0.0196 (10)
C13B0.0403 (8)0.0457 (8)0.0462 (8)0.0109 (7)0.0081 (7)0.0163 (7)
C14B0.0606 (11)0.0508 (10)0.0624 (11)0.0087 (9)0.0162 (9)0.0231 (9)
C15B0.0817 (16)0.0453 (11)0.0990 (18)0.0122 (10)0.0216 (14)0.0294 (12)
C16B0.0798 (16)0.0501 (12)0.0991 (18)0.0207 (11)0.0317 (14)0.0121 (12)
C17B0.0826 (15)0.0662 (14)0.0705 (14)0.0234 (12)0.0355 (12)0.0127 (11)
C18B0.0707 (12)0.0551 (11)0.0549 (10)0.0219 (9)0.0234 (9)0.0224 (9)
C19B0.0397 (8)0.0447 (8)0.0555 (9)0.0153 (7)0.0113 (7)0.0246 (8)
C20B0.0375 (7)0.0405 (8)0.0454 (8)0.0138 (6)0.0090 (6)0.0191 (7)
C21B0.0498 (9)0.0523 (10)0.0489 (9)0.0176 (8)0.0171 (7)0.0177 (8)
C22B0.0642 (12)0.0592 (11)0.0425 (9)0.0170 (9)0.0089 (8)0.0095 (8)
C23B0.0504 (10)0.0468 (9)0.0532 (10)0.0100 (8)0.0002 (8)0.0124 (8)
C24B0.0399 (8)0.0424 (8)0.0559 (9)0.0106 (6)0.0081 (7)0.0234 (7)
C25B0.0419 (8)0.0427 (8)0.0446 (8)0.0126 (6)0.0078 (6)0.0232 (7)
Geometric parameters (Å, º) top
Sn1A—O1A2.0621 (14)Sn1B—O1B2.0836 (12)
Sn1A—C7A2.108 (2)Sn1B—C13B2.1224 (17)
Sn1A—C13A2.1221 (18)Sn1B—C6B2.1289 (16)
Sn1A—C6A2.1302 (19)Sn1B—C7B2.1343 (17)
N1A—C25A1.334 (3)N1B—C25B1.338 (2)
N1A—H1NA0.84 (3)N1B—H1NB0.84 (2)
N1A—H2NA0.84 (3)N1B—H2NB0.83 (2)
N2A—O4A1.219 (2)N2B—O4B1.225 (2)
N2A—O3A1.235 (2)N2B—O3B1.240 (2)
N2A—C24A1.445 (3)N2B—C24B1.447 (2)
O1A—C19A1.300 (2)O1B—C19B1.305 (2)
O2A—C19A1.225 (3)O2B—C19B1.239 (2)
C1A—C2A1.382 (3)C1B—C6B1.382 (3)
C1A—C6A1.390 (3)C1B—C2B1.383 (3)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.374 (3)C2B—C3B1.361 (4)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.365 (3)C3B—C4B1.351 (4)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.374 (3)C4B—C5B1.378 (3)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.395 (3)C5B—C6B1.377 (2)
C5A—H5AA0.9300C5B—H5BA0.9300
C7A—C8A1.371 (3)C7B—C12B1.380 (3)
C7A—C12A1.382 (3)C7B—C8B1.387 (3)
C8A—C9A1.373 (4)C8B—C9B1.382 (3)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.342 (4)C9B—C10B1.372 (3)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.370 (5)C10B—C11B1.371 (4)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.383 (4)C11B—C12B1.386 (3)
C11A—H11A0.9300C11B—H11B0.9300
C12A—H12A0.9300C12B—H12B0.9300
C13A—C18A1.388 (3)C13B—C14B1.384 (3)
C13A—C14A1.389 (3)C13B—C18B1.386 (2)
C14A—C15A1.385 (3)C14B—C15B1.389 (3)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.378 (3)C15B—C16B1.361 (4)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.365 (3)C16B—C17B1.357 (3)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.386 (3)C17B—C18B1.378 (3)
C17A—H17A0.9300C17B—H17B0.9300
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.498 (3)C19B—C20B1.480 (2)
C20A—C21A1.378 (3)C20B—C21B1.375 (2)
C20A—C25A1.432 (3)C20B—C25B1.427 (2)
C21A—C22A1.392 (3)C21B—C22B1.388 (3)
C21A—H21A0.9300C21B—H21B0.9300
C22A—C23A1.358 (3)C22B—C23B1.368 (3)
C22A—H22A0.9300C22B—H22B0.9300
C23A—C24A1.387 (3)C23B—C24B1.388 (3)
C23A—H23A0.9300C23B—H23B0.9300
C24A—C25A1.422 (3)C24B—C25B1.420 (2)
O1A—Sn1A—C7A104.63 (7)O1B—Sn1B—C13B112.17 (6)
O1A—Sn1A—C13A111.31 (6)O1B—Sn1B—C6B96.96 (6)
C7A—Sn1A—C13A117.86 (7)C13B—Sn1B—C6B111.36 (7)
O1A—Sn1A—C6A92.35 (6)O1B—Sn1B—C7B111.49 (6)
C7A—Sn1A—C6A116.06 (7)C13B—Sn1B—C7B115.50 (6)
C13A—Sn1A—C6A111.28 (7)C6B—Sn1B—C7B107.75 (7)
C25A—N1A—H1NA119.3 (18)C25B—N1B—H1NB119.7 (15)
C25A—N1A—H2NA117.2 (17)C25B—N1B—H2NB115.4 (15)
H1NA—N1A—H2NA123 (3)H1NB—N1B—H2NB125 (2)
O4A—N2A—O3A121.1 (2)O4B—N2B—O3B121.77 (17)
O4A—N2A—C24A119.2 (2)O4B—N2B—C24B118.73 (17)
O3A—N2A—C24A119.66 (18)O3B—N2B—C24B119.49 (15)
C19A—O1A—Sn1A116.68 (14)C19B—O1B—Sn1B105.37 (10)
C2A—C1A—C6A120.27 (19)C6B—C1B—C2B120.7 (2)
C2A—C1A—H1AA119.9C6B—C1B—H1BA119.7
C6A—C1A—H1AA119.9C2B—C1B—H1BA119.7
C3A—C2A—C1A120.9 (2)C3B—C2B—C1B120.4 (2)
C3A—C2A—H2AA119.6C3B—C2B—H2BA119.8
C1A—C2A—H2AA119.6C1B—C2B—H2BA119.8
C4A—C3A—C2A119.4 (2)C4B—C3B—C2B119.7 (2)
C4A—C3A—H3AA120.3C4B—C3B—H3BA120.1
C2A—C3A—H3AA120.3C2B—C3B—H3BA120.1
C3A—C4A—C5A120.6 (2)C3B—C4B—C5B120.5 (2)
C3A—C4A—H4AA119.7C3B—C4B—H4BA119.7
C5A—C4A—H4AA119.7C5B—C4B—H4BA119.7
C4A—C5A—C6A121.00 (19)C6B—C5B—C4B121.2 (2)
C4A—C5A—H5AA119.5C6B—C5B—H5BA119.4
C6A—C5A—H5AA119.5C4B—C5B—H5BA119.4
C1A—C6A—C5A117.86 (18)C5B—C6B—C1B117.59 (17)
C1A—C6A—Sn1A122.98 (15)C5B—C6B—Sn1B122.68 (13)
C5A—C6A—Sn1A119.03 (14)C1B—C6B—Sn1B119.60 (14)
C8A—C7A—C12A116.9 (2)C12B—C7B—C8B118.21 (17)
C8A—C7A—Sn1A122.62 (17)C12B—C7B—Sn1B118.28 (14)
C12A—C7A—Sn1A120.47 (18)C8B—C7B—Sn1B123.46 (14)
C7A—C8A—C9A121.8 (3)C9B—C8B—C7B120.8 (2)
C7A—C8A—H8AA119.1C9B—C8B—H8BA119.6
C9A—C8A—H8AA119.1C7B—C8B—H8BA119.6
C10A—C9A—C8A120.7 (3)C10B—C9B—C8B120.1 (2)
C10A—C9A—H9AA119.6C10B—C9B—H9BA119.9
C8A—C9A—H9AA119.6C8B—C9B—H9BA119.9
C9A—C10A—C11A119.4 (3)C11B—C10B—C9B120.0 (2)
C9A—C10A—H10A120.3C11B—C10B—H10B120.0
C11A—C10A—H10A120.3C9B—C10B—H10B120.0
C10A—C11A—C12A120.0 (3)C10B—C11B—C12B119.8 (2)
C10A—C11A—H11A120.0C10B—C11B—H11B120.1
C12A—C11A—H11A120.0C12B—C11B—H11B120.1
C7A—C12A—C11A121.1 (3)C7B—C12B—C11B121.1 (2)
C7A—C12A—H12A119.5C7B—C12B—H12B119.5
C11A—C12A—H12A119.5C11B—C12B—H12B119.5
C18A—C13A—C14A118.41 (17)C14B—C13B—C18B118.06 (17)
C18A—C13A—Sn1A117.13 (13)C14B—C13B—Sn1B120.07 (14)
C14A—C13A—Sn1A124.24 (14)C18B—C13B—Sn1B121.73 (13)
C15A—C14A—C13A120.58 (19)C13B—C14B—C15B120.3 (2)
C15A—C14A—H14A119.7C13B—C14B—H14B119.8
C13A—C14A—H14A119.7C15B—C14B—H14B119.8
C16A—C15A—C14A119.8 (2)C16B—C15B—C14B120.1 (2)
C16A—C15A—H15A120.1C16B—C15B—H15B119.9
C14A—C15A—H15A120.1C14B—C15B—H15B119.9
C17A—C16A—C15A120.56 (19)C17B—C16B—C15B120.4 (2)
C17A—C16A—H16A119.7C17B—C16B—H16B119.8
C15A—C16A—H16A119.7C15B—C16B—H16B119.8
C16A—C17A—C18A119.78 (19)C16B—C17B—C18B120.2 (2)
C16A—C17A—H17A120.1C16B—C17B—H17B119.9
C18A—C17A—H17A120.1C18B—C17B—H17B119.9
C17A—C18A—C13A120.87 (18)C17B—C18B—C13B120.86 (19)
C17A—C18A—H18A119.6C17B—C18B—H18B119.6
C13A—C18A—H18A119.6C13B—C18B—H18B119.6
O2A—C19A—O1A121.92 (19)O2B—C19B—O1B119.18 (15)
O2A—C19A—C20A124.23 (19)O2B—C19B—C20B123.75 (15)
O1A—C19A—C20A113.85 (18)O1B—C19B—C20B117.07 (15)
C21A—C20A—C25A120.37 (18)C21B—C20B—C25B120.08 (15)
C21A—C20A—C19A118.65 (18)C21B—C20B—C19B118.97 (15)
C25A—C20A—C19A120.98 (17)C25B—C20B—C19B120.95 (14)
C20A—C21A—C22A122.0 (2)C20B—C21B—C22B122.50 (17)
C20A—C21A—H21A119.0C20B—C21B—H21B118.8
C22A—C21A—H21A119.0C22B—C21B—H21B118.8
C23A—C22A—C21A119.0 (2)C23B—C22B—C21B118.82 (17)
C23A—C22A—H22A120.5C23B—C22B—H22B120.6
C21A—C22A—H22A120.5C21B—C22B—H22B120.6
C22A—C23A—C24A120.8 (2)C22B—C23B—C24B120.39 (17)
C22A—C23A—H23A119.6C22B—C23B—H23B119.8
C24A—C23A—H23A119.6C24B—C23B—H23B119.8
C23A—C24A—C25A122.25 (18)C23B—C24B—C25B122.25 (16)
C23A—C24A—N2A116.25 (18)C23B—C24B—N2B116.73 (15)
C25A—C24A—N2A121.49 (18)C25B—C24B—N2B120.99 (16)
N1A—C25A—C24A124.23 (19)N1B—C25B—C24B123.63 (16)
N1A—C25A—C20A120.28 (18)N1B—C25B—C20B120.39 (16)
C24A—C25A—C20A115.49 (17)C24B—C25B—C20B115.95 (15)
C7A—Sn1A—O1A—C19A60.17 (16)C13B—Sn1B—O1B—C19B66.64 (12)
C13A—Sn1A—O1A—C19A68.16 (16)C6B—Sn1B—O1B—C19B176.88 (11)
C6A—Sn1A—O1A—C19A177.90 (15)C7B—Sn1B—O1B—C19B64.66 (12)
C6A—C1A—C2A—C3A1.0 (3)C6B—C1B—C2B—C3B0.4 (4)
C1A—C2A—C3A—C4A0.1 (3)C1B—C2B—C3B—C4B0.1 (4)
C2A—C3A—C4A—C5A0.9 (3)C2B—C3B—C4B—C5B0.2 (4)
C3A—C4A—C5A—C6A0.6 (3)C3B—C4B—C5B—C6B0.1 (4)
C2A—C1A—C6A—C5A1.3 (3)C4B—C5B—C6B—C1B0.2 (3)
C2A—C1A—C6A—Sn1A174.47 (15)C4B—C5B—C6B—Sn1B175.92 (16)
C4A—C5A—C6A—C1A0.5 (3)C2B—C1B—C6B—C5B0.5 (4)
C4A—C5A—C6A—Sn1A175.45 (15)C2B—C1B—C6B—Sn1B176.3 (2)
O1A—Sn1A—C6A—C1A140.20 (15)O1B—Sn1B—C6B—C5B7.96 (17)
C7A—Sn1A—C6A—C1A32.66 (17)C13B—Sn1B—C6B—C5B125.08 (16)
C13A—Sn1A—C6A—C1A105.83 (15)C7B—Sn1B—C6B—C5B107.29 (16)
O1A—Sn1A—C6A—C5A35.51 (15)O1B—Sn1B—C6B—C1B176.38 (17)
C7A—Sn1A—C6A—C5A143.05 (14)C13B—Sn1B—C6B—C1B59.26 (18)
C13A—Sn1A—C6A—C5A78.46 (15)C7B—Sn1B—C6B—C1B68.37 (18)
O1A—Sn1A—C7A—C8A114.3 (2)O1B—Sn1B—C7B—C12B102.93 (15)
C13A—Sn1A—C7A—C8A9.9 (2)C13B—Sn1B—C7B—C12B127.50 (15)
C6A—Sn1A—C7A—C8A145.6 (2)C6B—Sn1B—C7B—C12B2.31 (16)
O1A—Sn1A—C7A—C12A67.1 (2)O1B—Sn1B—C7B—C8B79.86 (16)
C13A—Sn1A—C7A—C12A168.65 (18)C13B—Sn1B—C7B—C8B49.71 (17)
C6A—Sn1A—C7A—C12A33.0 (2)C6B—Sn1B—C7B—C8B174.90 (15)
C12A—C7A—C8A—C9A0.4 (4)C12B—C7B—C8B—C9B1.2 (3)
Sn1A—C7A—C8A—C9A178.2 (2)Sn1B—C7B—C8B—C9B178.44 (16)
C7A—C8A—C9A—C10A0.6 (5)C7B—C8B—C9B—C10B0.0 (3)
C8A—C9A—C10A—C11A2.0 (6)C8B—C9B—C10B—C11B0.5 (4)
C9A—C10A—C11A—C12A2.5 (6)C9B—C10B—C11B—C12B0.3 (4)
C8A—C7A—C12A—C11A0.1 (4)C8B—C7B—C12B—C11B2.0 (3)
Sn1A—C7A—C12A—C11A178.7 (2)Sn1B—C7B—C12B—C11B179.35 (18)
C10A—C11A—C12A—C7A1.5 (5)C10B—C11B—C12B—C7B1.5 (4)
O1A—Sn1A—C13A—C18A112.38 (13)O1B—Sn1B—C13B—C14B96.73 (15)
C7A—Sn1A—C13A—C18A126.77 (13)C6B—Sn1B—C13B—C14B10.72 (16)
C6A—Sn1A—C13A—C18A10.89 (15)C7B—Sn1B—C13B—C14B134.04 (14)
O1A—Sn1A—C13A—C14A73.02 (17)O1B—Sn1B—C13B—C18B87.64 (15)
C7A—Sn1A—C13A—C14A47.83 (18)C6B—Sn1B—C13B—C18B164.91 (14)
C6A—Sn1A—C13A—C14A174.51 (15)C7B—Sn1B—C13B—C18B41.60 (17)
C18A—C13A—C14A—C15A0.9 (3)C18B—C13B—C14B—C15B0.8 (3)
Sn1A—C13A—C14A—C15A173.58 (16)Sn1B—C13B—C14B—C15B175.01 (17)
C13A—C14A—C15A—C16A1.5 (3)C13B—C14B—C15B—C16B0.3 (4)
C14A—C15A—C16A—C17A1.1 (3)C14B—C15B—C16B—C17B0.5 (4)
C15A—C16A—C17A—C18A0.3 (3)C15B—C16B—C17B—C18B0.3 (4)
C16A—C17A—C18A—C13A0.3 (3)C16B—C17B—C18B—C13B1.4 (4)
C14A—C13A—C18A—C17A0.1 (3)C14B—C13B—C18B—C17B1.6 (3)
Sn1A—C13A—C18A—C17A174.86 (14)Sn1B—C13B—C18B—C17B174.13 (17)
Sn1A—O1A—C19A—O2A7.5 (3)Sn1B—O1B—C19B—O2B0.83 (18)
Sn1A—O1A—C19A—C20A172.66 (12)Sn1B—O1B—C19B—C20B179.09 (11)
O2A—C19A—C20A—C21A176.47 (19)O2B—C19B—C20B—C21B178.42 (17)
O1A—C19A—C20A—C21A3.7 (3)O1B—C19B—C20B—C21B1.5 (2)
O2A—C19A—C20A—C25A3.2 (3)O2B—C19B—C20B—C25B1.7 (2)
O1A—C19A—C20A—C25A176.63 (16)O1B—C19B—C20B—C25B178.38 (14)
C25A—C20A—C21A—C22A1.3 (3)C25B—C20B—C21B—C22B1.4 (3)
C19A—C20A—C21A—C22A179.03 (19)C19B—C20B—C21B—C22B178.70 (17)
C20A—C21A—C22A—C23A1.0 (3)C20B—C21B—C22B—C23B1.4 (3)
C21A—C22A—C23A—C24A1.9 (3)C21B—C22B—C23B—C24B0.3 (3)
C22A—C23A—C24A—C25A0.4 (3)C22B—C23B—C24B—C25B0.8 (3)
C22A—C23A—C24A—N2A179.87 (19)C22B—C23B—C24B—N2B177.28 (18)
O4A—N2A—C24A—C23A6.1 (3)O4B—N2B—C24B—C23B7.7 (3)
O3A—N2A—C24A—C23A173.9 (2)O3B—N2B—C24B—C23B171.67 (18)
O4A—N2A—C24A—C25A173.64 (18)O4B—N2B—C24B—C25B170.48 (18)
O3A—N2A—C24A—C25A6.3 (3)O3B—N2B—C24B—C25B10.2 (3)
C23A—C24A—C25A—N1A178.63 (19)C23B—C24B—C25B—N1B179.08 (18)
N2A—C24A—C25A—N1A1.6 (3)N2B—C24B—C25B—N1B1.1 (3)
C23A—C24A—C25A—C20A1.8 (3)C23B—C24B—C25B—C20B0.8 (2)
N2A—C24A—C25A—C20A177.91 (16)N2B—C24B—C25B—C20B177.20 (15)
C21A—C20A—C25A—N1A177.84 (18)C21B—C20B—C25B—N1B178.04 (18)
C19A—C20A—C25A—N1A1.9 (3)C19B—C20B—C25B—N1B1.8 (2)
C21A—C20A—C25A—C24A2.6 (2)C21B—C20B—C25B—C24B0.3 (2)
C19A—C20A—C25A—C24A177.70 (15)C19B—C20B—C25B—C24B179.85 (14)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1A–C6A phenyl ring.
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O3A0.84 (3)2.02 (3)2.632 (3)129 (2)
N1A—H2NA···O2A0.84 (3)1.99 (3)2.671 (3)138 (2)
N1B—H1NB···O2B0.84 (2)1.98 (3)2.643 (3)135 (2)
N1B—H2NB···O3B0.83 (2)1.96 (2)2.607 (3)135.3 (19)
C15B—H15B···Cg1i0.932.843.596 (3)139
Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Sn(C6H5)3(C7H5N2O4)]
Mr531.12
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)11.2836 (1), 14.9600 (2), 15.1828 (3)
α, β, γ (°)109.257 (1), 98.503 (1), 105.743 (1)
V3)2247.89 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.17
Crystal size (mm)0.44 × 0.32 × 0.19
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.628, 0.810
No. of measured, independent and
observed [I > 2σ(I)] reflections
69259, 18711, 12707
Rint0.027
(sin θ/λ)max1)0.796
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.080, 1.01
No. of reflections18711
No. of parameters593
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.70, 0.42

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1A–C6A phenyl ring.
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O3A0.84 (3)2.02 (3)2.632 (3)129 (2)
N1A—H2NA···O2A0.84 (3)1.99 (3)2.671 (3)138 (2)
N1B—H1NB···O2B0.84 (2)1.98 (3)2.643 (3)135 (2)
N1B—H2NB···O3B0.83 (2)1.96 (2)2.607 (3)135.3 (19)
C15B—H15B···Cg1i0.93002.843.596 (3)139
Symmetry code: (i) x, y+1, z+1.
 

Footnotes

Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors would like to thank Universiti Tunku Abdul Rahman (UTAR) and Universiti Sains Malaysia (USM) for financial support as well as technical assistance and facilities. HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWin, Y. F., Teoh, S. G., Ha, S. T., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, m1530–m1531.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWin, Y. F., Teoh, S. G., Vikneswaran, M. R., Goh, J. H. & Fun, H.-K. (2010). Acta Cryst. E66, m695–m696.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWin, Y. F., Teoh, S.-G., Zakaria, L., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, m348–m350.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYeap, L.-L. & Teoh, S.-G. (2003). J. Coord. Chem. 56, 701–708.  Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 5| May 2011| Pages m561-m562
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