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

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ISSN: 2056-9890

Di-n-butyl­bis­(N-n-butyl-N-ethyl­di­thio­carbamato-κS)tin(IV)

aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor Darul Ehsan, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 17 April 2009; accepted 22 April 2009; online 30 April 2009)

The Sn atom in the title compound, [Sn(C4H9)2(C7H14NS2)2], exists in a tetra­hedral C2S2Sn coordination geometry. The geometry is distorted towards skew-trapezoidal-bipyramidal owing to the proximity of the double-bond S atoms [Sn—S = 2.521 (2) and Sn⋯S = 2.933 (2) Å]. The Sn atom lies on a special position of mm2 site symmetry and the tin-bound n-butyl chain is disordered about a mirror plane. The ethyl and n-butyl groups of the dithio­carbamate unit are disordered about another mirror plane.

Related literature

For other di-n-butyl­tin dithio­carbamates, see: Farina et al. (2000[Farina, Y., Baba, I., Othman, A. H. & Ng, S. W. (2000). Main Group Met. Chem. 23, 795-796.]); Lokaj et al. (1986[Lokaj, J., Kellö, E., Kettmann, V., Vrábel, V. & Rattay, V. (1986). Collect. Czech. Chem. Commun. 51, 2521-2527.]); Menezes et al. (2005[Menezes, D. C., Vieira, F. T., de Lima, G. M., Porto, A. O., Cortes, M. E., Ardisson, J. D. & Albrecht-Schmitt, T. E. (2005). Eur. J. Med. Chem. 40, 1277-1282.]); Vrábel et al. (1992a[Vrábel, V., Lokaj, J., Kellö, E., Rattay, V., Batsanov, A. C. & Struchkov, Yu. T. (1992a). Acta Cryst. C48, 627-629.],b[Vrábel, V., Lokaj, J., Kellö, E., Garaj, J., Batsanov, A. C. & Struchkov, Yu. T. (1992b). Acta Cryst. C48, 633-635.]); Vrábel & Kellö (1993[Vrábel, V. & Kellö, E. (1993). Acta Cryst. C49, 873-875.]); Zia-ur-Rehman et al. (2006[Zia-ur-Rehman, Shahzadi, S., Ali, S., Badshah, A. & Jin, G.-X. (2006). J. Iran. Chem. Soc. 3, 157-160.]). For a review of the applications and structures of tin dithio­carbamates, see: Tiekink (2008[Tiekink, E. R. T. (2008). Appl. Organomet. Chem. 22, 533-550.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C4H9)2(C7H14NS2)2]

  • Mr = 585.54

  • Orthorhombic, P m m n

  • a = 11.1317 (2) Å

  • b = 19.4349 (3) Å

  • c = 7.7262 (1) Å

  • V = 1671.51 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.02 mm−1

  • T = 123 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.749, Tmax = 0.821

  • 11224 measured reflections

  • 2072 independent reflections

  • 1667 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.239

  • S = 1.11

  • 2072 reflections

  • 131 parameters

  • 55 restraints

  • H-atom parameters constrained

  • Δρmax = 1.03 e Å−3

  • Δρmin = −0.66 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For other di-n-butyltin dithiocarbamates, see: Farina et al. (2000); Lokaj et al. (1986); Menezes et al. (2005); Vrábel et al. (1992a,b); Vrábel & Kellö (1993); Zia-ur-Rehman et al. (2006). For a review of the applications and structures of tin dithiocarbamates, see: Tiekink (2008).

Experimental top

Carbon disulfide (4 ml, 0.06 mol) was added to n-butylisopropylamine (8 ml, 0.06 mol) in ethanol (50 ml) at 277 K. Dibutyltin dichloride (9.1 g, 0.03 mol) dissolved in ethanol (50 ml) was added. The white solid that precipitated was collected and recrystallized from ethanol.

Refinement top

The tin-bound butyl chain was allowed to refined off the mirror plane, as were the ethyl and butyl groups of the dithiocarbamate anion. 1,2-Related carbon-carbon distances were restrained to 1.54±0.01 Å and the 1,3-related ones to 2.51±0.02 Å. The N1–C6 and N1–C6' pair of distances were restrained to 0.01 Å as were the N1–C8 and N1–C8' pair. The temperature factors of the primed atoms were restrained to those of the unprimed ones; the anisotropic displacement parameters of the primed atoms were restrained to be nearly isotropic.

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The final difference Fourier map had a large peak in the vicinity of the C9' atom.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of dibutyldi(N-butyl-N-ethylbutyldithiocarbamato)tin at the 70% probability level; the disorder is not shown. Unlabelled atoms are related by a 2-fold axis. Hydrogen atoms are drawn as spheres of arbitrary radius.
Di-n-butylbis(N-n-butyl-N-ethyldithiocarbamato- κS)tin(IV) top
Crystal data top
[Sn(C4H9)2(C7H14NS2)2]F(000) = 612
Mr = 585.54Dx = 1.163 Mg m3
Orthorhombic, PmmnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2aCell parameters from 5407 reflections
a = 11.1317 (2) Åθ = 2.8–28.2°
b = 19.4349 (3) ŵ = 1.02 mm1
c = 7.7262 (1) ÅT = 123 K
V = 1671.51 (5) Å3Block, colorless
Z = 20.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART APEX
diffractometer
2072 independent reflections
Radiation source: fine-focus sealed tube1667 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.749, Tmax = 0.821k = 2425
11224 measured reflectionsl = 109
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.239H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.1484P)2 + 2.8257P]
where P = (Fo2 + 2Fc2)/3
2072 reflections(Δ/σ)max = 0.001
131 parametersΔρmax = 1.03 e Å3
55 restraintsΔρmin = 0.66 e Å3
Crystal data top
[Sn(C4H9)2(C7H14NS2)2]V = 1671.51 (5) Å3
Mr = 585.54Z = 2
Orthorhombic, PmmnMo Kα radiation
a = 11.1317 (2) ŵ = 1.02 mm1
b = 19.4349 (3) ÅT = 123 K
c = 7.7262 (1) Å0.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART APEX
diffractometer
2072 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1667 reflections with I > 2σ(I)
Tmin = 0.749, Tmax = 0.821Rint = 0.024
11224 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06655 restraints
wR(F2) = 0.239H-atom parameters constrained
S = 1.11Δρmax = 1.03 e Å3
2072 reflectionsΔρmin = 0.66 e Å3
131 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.75000.25000.43290 (7)0.0602 (4)
S10.75000.33480 (11)0.6798 (2)0.0659 (6)
S20.75000.39534 (11)0.3309 (3)0.0852 (9)
N10.75000.4700 (4)0.6210 (11)0.0661 (18)
C10.5831 (12)0.257 (4)0.3153 (12)0.085 (10)0.50
H1A0.53150.21900.35800.102*0.50
H1B0.54480.30080.34880.102*0.50
C20.5905 (11)0.2529 (13)0.1171 (11)0.100 (5)0.50
H2A0.64370.29010.07520.120*0.50
H2B0.62770.20850.08430.120*0.50
C30.4697 (14)0.2591 (17)0.0264 (19)0.107 (9)0.50
H3A0.48140.25810.10060.129*0.50
H3B0.43140.30340.05730.129*0.50
C40.3882 (18)0.1990 (16)0.082 (3)0.130 (9)0.50
H4A0.30750.20580.03450.195*0.50
H4B0.38390.19730.20870.195*0.50
H4C0.42150.15570.03840.195*0.50
C50.75000.4065 (5)0.5500 (10)0.0576 (18)
C60.744 (3)0.4806 (13)0.8169 (16)0.085 (4)0.25
H6A0.71810.52820.84260.102*0.25
H6B0.68490.44850.86780.102*0.25
C70.865 (3)0.4679 (13)0.8947 (16)0.049 (4)0.25
H7A0.86100.47551.02000.074*0.25
H7B0.92350.49960.84370.074*0.25
H7C0.88960.42040.87160.074*0.25
C6'0.732 (3)0.4781 (19)0.8168 (18)0.085 (4)0.25
H6'10.69800.43540.86680.102*0.25
H6'20.67640.51660.84150.102*0.25
C7'0.857 (3)0.4929 (13)0.895 (3)0.049 (4)0.25
H7'10.84990.49941.01990.074*0.25
H7'20.89040.53460.84190.074*0.25
H7'30.91080.45390.87110.074*0.25
C80.7479 (19)0.5360 (8)0.521 (3)0.083 (4)0.50
H8A0.72110.57390.59710.100*0.25
H8B0.69010.53210.42400.100*0.25
C90.8705 (19)0.5520 (8)0.451 (3)0.047 (4)0.25
H9A0.89420.51470.37060.056*0.25
H9B0.92830.55190.54830.056*0.25
C100.8813 (14)0.6206 (8)0.356 (3)0.042 (3)0.25
H10A0.94890.61860.27270.050*0.25
H10B0.89790.65790.43980.050*0.25
C110.764 (3)0.6359 (14)0.259 (4)0.102 (6)0.25
H11A0.76470.68370.21780.153*0.25
H11B0.69550.62910.33650.153*0.25
H11C0.75670.60480.15920.153*0.25
C8'0.734 (3)0.5340 (12)0.513 (5)0.083 (4)0.25
H8C0.67700.56550.57250.100*0.25
H8D0.69850.52150.39990.100*0.25
C9'0.8539 (19)0.5710 (11)0.485 (3)0.047 (4)0.25
H9C0.88730.58510.59820.056*0.25
H9D0.91140.53880.43020.056*0.25
C10'0.8399 (14)0.6346 (8)0.370 (3)0.042 (3)0.25
H10C0.85620.62180.24820.050*0.25
H10D0.89990.66960.40460.050*0.25
C11'0.7130 (18)0.6661 (16)0.383 (4)0.102 (6)0.25
H11D0.70180.69970.28980.153*0.25
H11E0.70370.68890.49510.153*0.25
H11F0.65280.62950.37170.153*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.1059 (7)0.0502 (5)0.0245 (4)0.0000.0000.000
S10.1097 (17)0.0588 (11)0.0292 (8)0.0000.0000.0063 (7)
S20.172 (3)0.0471 (11)0.0367 (9)0.0000.0000.0001 (8)
N10.080 (4)0.055 (4)0.064 (4)0.0000.0000.018 (3)
C10.112 (9)0.08 (3)0.062 (6)0.03 (2)0.015 (6)0.007 (11)
C20.135 (11)0.112 (11)0.053 (5)0.075 (14)0.011 (7)0.029 (11)
C30.145 (13)0.11 (2)0.070 (7)0.041 (19)0.030 (9)0.006 (12)
C40.137 (18)0.16 (2)0.089 (13)0.024 (18)0.032 (12)0.002 (13)
C50.073 (5)0.057 (4)0.043 (4)0.0000.0000.006 (3)
C60.086 (8)0.091 (6)0.077 (6)0.000 (8)0.029 (8)0.042 (5)
C70.048 (5)0.066 (11)0.034 (4)0.002 (9)0.017 (4)0.016 (6)
C6'0.086 (8)0.091 (6)0.077 (6)0.000 (8)0.029 (8)0.042 (5)
C7'0.048 (5)0.066 (11)0.034 (4)0.002 (9)0.017 (4)0.016 (6)
C80.068 (7)0.063 (5)0.118 (7)0.021 (8)0.010 (9)0.001 (5)
C90.040 (6)0.057 (8)0.044 (7)0.002 (6)0.011 (5)0.013 (7)
C100.031 (8)0.035 (6)0.058 (6)0.010 (5)0.014 (6)0.005 (5)
C110.119 (11)0.092 (9)0.095 (9)0.039 (9)0.007 (8)0.002 (7)
C8'0.068 (7)0.063 (5)0.118 (7)0.021 (8)0.010 (9)0.001 (5)
C9'0.040 (6)0.057 (8)0.044 (7)0.002 (6)0.011 (5)0.013 (7)
C10'0.031 (8)0.035 (6)0.058 (6)0.010 (5)0.014 (6)0.005 (5)
C11'0.119 (11)0.092 (9)0.095 (9)0.039 (9)0.007 (8)0.002 (7)
Geometric parameters (Å, º) top
Sn1—C12.073 (13)C7—H7B0.9800
Sn1—C1i2.073 (13)C7—H7C0.9800
Sn1—C1ii2.073 (13)C6'—C7'1.545 (10)
Sn1—C1iii2.073 (13)C6'—H6'10.9900
Sn1—S12.5211 (19)C6'—H6'20.9900
Sn1—S1iii2.5211 (19)C7'—H7'10.9800
S1—C51.718 (9)C7'—H7'20.9800
S2—C51.707 (8)C7'—H7'30.9800
N1—C51.350 (11)C8—C91.4998
N1—C81.499 (14)C8—H8A0.9900
N1—C8'1.508 (15)C8—H8B0.9900
N1—C8'ii1.508 (15)C9—C101.527 (9)
N1—C61.528 (14)C9—H9A0.9900
N1—C6ii1.528 (14)C9—H9B0.9900
N1—C6'ii1.534 (15)C10—C111.536 (10)
N1—C6'1.534 (15)C10—H10A0.9900
C1—C21.536 (9)C10—H10B0.9900
C1—H1A0.9900C11—H11A0.9800
C1—H1B0.9900C11—H11B0.9800
C2—C31.520 (9)C11—H11C0.9800
C2—H2A0.9900C8'—C9'1.536 (10)
C2—H2B0.9900C8'—H8C0.9900
C3—C41.540 (10)C8'—H8D0.9900
C3—H3A0.9900C9'—C10'1.529 (10)
C3—H3B0.9900C9'—H9C0.9900
C4—H4A0.9800C9'—H9D0.9900
C4—H4B0.9800C10'—C11'1.543 (10)
C4—H4C0.9800C10'—H10C0.9900
C6—C71.4925C10'—H10D0.9900
C6—H6A0.9900C11'—H11D0.9800
C6—H6B0.9900C11'—H11E0.9800
C7—H7A0.9800C11'—H11F0.9800
C1—Sn1—C1ii127.4 (9)C6—C7—H7A109.5
C1i—Sn1—C1ii128.0 (6)C6—C7—H7B109.5
C1—Sn1—C1iii128.0 (6)H7A—C7—H7B109.5
C1i—Sn1—C1iii127.4 (9)C6—C7—H7C109.5
C1—Sn1—S1106.9 (14)H7A—C7—H7C109.5
C1i—Sn1—S1111.9 (15)H7B—C7—H7C109.5
C1ii—Sn1—S1106.9 (14)N1—C6'—C7'106.5 (19)
C1iii—Sn1—S1111.9 (15)N1—C6'—H6'1110.4
C1—Sn1—S1iii111.9 (15)C7'—C6'—H6'1110.4
C1i—Sn1—S1iii106.9 (14)N1—C6'—H6'2110.4
C1ii—Sn1—S1iii111.9 (15)C7'—C6'—H6'2110.4
C1iii—Sn1—S1iii106.9 (14)H6'1—C6'—H6'2108.6
S1—Sn1—S1iii81.64 (10)C6'—C7'—H7'1109.5
C5—S1—Sn195.1 (3)C6'—C7'—H7'2109.5
C5—N1—C8124.9 (12)H7'1—C7'—H7'2109.5
C5—N1—C8'122.0 (17)C6'—C7'—H7'3109.5
C5—N1—C8'ii122.0 (17)H7'1—C7'—H7'3109.5
C5—N1—C6121.7 (12)H7'2—C7'—H7'3109.5
C8—N1—C6113.3 (14)N1—C8—C9110.5 (8)
C8'—N1—C6115.5 (18)N1—C8—H8A109.6
C8'ii—N1—C6116.1 (19)C9—C8—H8A109.6
C5—N1—C6ii121.7 (12)N1—C8—H8B109.6
C8—N1—C6ii113.4 (14)C9—C8—H8B109.6
C8'—N1—C6ii116.1 (19)H8A—C8—H8B108.1
C8'ii—N1—C6ii115.5 (18)C8—C9—C10115.2 (9)
C5—N1—C6'ii119.7 (16)C8—C9—H9A108.5
C8—N1—C6'ii115.1 (18)C10—C9—H9A108.5
C8'—N1—C6'ii118 (2)C8—C9—H9B108.5
C8'ii—N1—C6'ii116 (2)C10—C9—H9B108.5
C5—N1—C6'119.7 (16)H9A—C9—H9B107.5
C8—N1—C6'114.8 (18)C9—C10—C11109.7 (12)
C8'—N1—C6'116 (2)C9—C10—H10A109.7
C8'ii—N1—C6'118 (2)C11—C10—H10A109.7
C2—C1—Sn1112.7 (9)C9—C10—H10B109.7
C2—C1—H1A109.1C11—C10—H10B109.7
Sn1—C1—H1A109.1H10A—C10—H10B108.2
C2—C1—H1B109.1C10—C11—H11A109.5
Sn1—C1—H1B109.1C10—C11—H11B109.5
H1A—C1—H1B107.8H11A—C11—H11B109.5
C3—C2—C1114.1 (9)C10—C11—H11C109.5
C3—C2—H2A108.7H11A—C11—H11C109.5
C1—C2—H2A108.7H11B—C11—H11C109.5
C3—C2—H2B108.7N1—C8'—C9'111.1 (17)
C1—C2—H2B108.7N1—C8'—H8C109.4
H2A—C2—H2B107.6C9'—C8'—H8C109.4
C2—C3—C4109.4 (13)N1—C8'—H8D109.4
C2—C3—H3A109.8C9'—C8'—H8D109.4
C4—C3—H3A109.8H8C—C8'—H8D108.0
C2—C3—H3B109.8C10'—C9'—C8'111.9 (11)
C4—C3—H3B109.8C10'—C9'—H9C109.2
H3A—C3—H3B108.2C8'—C9'—H9C109.2
C3—C4—H4A109.5C10'—C9'—H9D109.2
C3—C4—H4B109.5C8'—C9'—H9D109.2
H4A—C4—H4B109.5H9C—C9'—H9D107.9
C3—C4—H4C109.5C9'—C10'—C11'112.1 (12)
H4A—C4—H4C109.5C9'—C10'—H10C109.2
H4B—C4—H4C109.5C11'—C10'—H10C109.2
N1—C5—S2121.3 (7)C9'—C10'—H10D109.2
N1—C5—S1120.3 (6)C11'—C10'—H10D109.2
S2—C5—S1118.4 (5)H10C—C10'—H10D107.9
C7—C6—N1109.8 (11)C10'—C11'—H11D109.5
C7—C6—H6A109.7C10'—C11'—H11E109.5
N1—C6—H6A109.7H11D—C11'—H11E109.5
C7—C6—H6B109.7C10'—C11'—H11F109.5
N1—C6—H6B109.7H11D—C11'—H11F109.5
H6A—C6—H6B108.2H11E—C11'—H11F109.5
C1—Sn1—S1—C569.5 (16)C6'ii—N1—C5—S18.7 (14)
C1i—Sn1—S1—C575.1 (16)C6'—N1—C5—S18.7 (14)
C1ii—Sn1—S1—C569.5 (16)Sn1—S1—C5—N1180.000 (3)
C1iii—Sn1—S1—C575.1 (16)Sn1—S1—C5—S20.000 (2)
S1iii—Sn1—S1—C5180.000 (2)C5—N1—C6—C778.1 (9)
C8—N1—C5—S21.1 (10)C8—N1—C6—C7105.3 (10)
C8'—N1—C5—S28.2 (12)C8'—N1—C6—C7112.2 (12)
C8'ii—N1—C5—S28.2 (12)C8'ii—N1—C6—C796.8 (13)
C6—N1—C5—S2177.2 (14)C6ii—N1—C6—C713.4 (4)
C6ii—N1—C5—S2177.2 (14)C5—N1—C8—C978.2 (8)
C6'ii—N1—C5—S2171.3 (14)C8'—N1—C8—C9144 (19)
C6'—N1—C5—S2171.3 (14)C8'ii—N1—C8—C96 (15)
C8—N1—C5—S1178.9 (10)C6—N1—C8—C9105.4 (14)
C8'—N1—C5—S1171.8 (12)C6ii—N1—C8—C9100.2 (14)
C8'ii—N1—C5—S1171.8 (12)C6'ii—N1—C8—C994.5 (15)
C6—N1—C5—S12.8 (14)C6'—N1—C8—C9111.1 (14)
C6ii—N1—C5—S12.8 (14)
Symmetry codes: (i) x, y+1/2, z; (ii) x+3/2, y, z; (iii) x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula[Sn(C4H9)2(C7H14NS2)2]
Mr585.54
Crystal system, space groupOrthorhombic, Pmmn
Temperature (K)123
a, b, c (Å)11.1317 (2), 19.4349 (3), 7.7262 (1)
V3)1671.51 (5)
Z2
Radiation typeMo Kα
µ (mm1)1.02
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.749, 0.821
No. of measured, independent and
observed [I > 2σ(I)] reflections
11224, 2072, 1667
Rint0.024
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.239, 1.11
No. of reflections2072
No. of parameters131
No. of restraints55
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.03, 0.66

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

We thank Universiti Kebangsaan Malaysia and the University of Malaya for supporting this study.

References

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