PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): m572.
Published online 2010 April 24. doi:  10.1107/S1600536810014662
PMCID: PMC2979056

Di-n-but­yl{4-hydr­oxy-N′-[(2-oxido-1-naphthyl-κO)methyl­ene]benzo­hydrazidato-κ2 O,N′}tin(IV)

Abstract

The deprotonated Schiff base ligand in the title compound, [Sn(C4H9)2(C18H12N2O3)], O,N,O′-chelates to the Sn atom, which is five-coordinated in a cis-C2NO2Sn trigonal-bipyramidal environment. The apical sites are occupied by the O atoms [O—Sn—O = 155.2 (2)°]. The hydr­oxy group is a hydrogen-bond donor to the two-coordinate N atom of an adjacent mol­ecule, the hydrogen-bonding inter­action giving rise to a helical chain running along the c axis. The carbon atoms of the butyl chains are equally disordered over two positions.

Related literature

For the synthesis of the Schiff base, see: Cui et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m572-scheme1.jpg

Experimental

Crystal data

  • [Sn(C4H9)2(C18H12N2O3)]
  • M r = 537.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m572-efi1.jpg
  • a = 11.6644 (9) Å
  • b = 17.2500 (14) Å
  • c = 12.9296 (11) Å
  • β = 106.793 (1)°
  • V = 2490.6 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.05 mm−1
  • T = 293 K
  • 0.40 × 0.40 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.678, T max = 0.902
  • 19289 measured reflections
  • 4391 independent reflections
  • 2953 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.189
  • S = 1.03
  • 4391 reflections
  • 314 parameters
  • 78 restraints
  • H-atom parameters constrained
  • Δρmax = 1.19 e Å−3
  • Δρmin = −1.14 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014662/bt5252sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014662/bt5252Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank MOSTI (grant No. 06-01-09-SF0046), Universiti Malaysia Sarawak and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

There are numerous reports of metal complexes of the Schiff bases derived by condensing salicylaldehyde (and related compounds) with benzohydrazide (and related compounds). E)-4-Hydroxy-N'-[(2-hydroxynaphthalen-1-yl)methylene]benzohydrazide is a less studied ligand. The deprotonated Schiff-base ligand in the title compound O,N,O'-chelates to the tin atom, which is five coordinate in a cis-C2NO2Sn trigonal bipyramidal environment (Scheme I, Fig. 1). The apical sites are occupied by the oxgen atoms [O–Sn–O 155.2 (2) °]. Both butyl chains are disordered over two positions in a 1:1 ratio.

Experimental

(E)-4-Hydroxy-N'-[(2-hydroxynaphthalen-1-yl)methylene]benzohydrazide was synthesized according to a literature method (Cui et al., 2007). The compound (0.61 g, 2 mmole) was dissolved in methanol (20 ml). Potassium hydroxide (0.23 g, 4 mmol) dissolved in methanol (5 ml) was added. The orange solution was then treated with di-n-butyltin dichloride (0.61 g, 2 mmol) in methanol (10 ml). The mixture was heated for an hour. The solution was filtered. The evaporation of the solvent gave a product that was recrystallized from ether in 70% yield; m.p. 455-457 K.

Refinement

Hydrogen atoms were placed in calculated positions (C—H 0.93 to 0.97, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5Ueq(C,O).

The carbon atoms of the butyl chains are disordered over two positions; the occupancy could not be refined, and was assumed to be 50:50. The 1,2-related carbon-carbon distances were restrained to 1.54±0.01Å and the 1,3-related ones to 2.51±0.01 Å. The displacement ellipsoids of the primed atoms were restrained to be similar to those of the unprimed ones; furthermore, the ADP's were restrained to be nearly isotropic.

The final difference Fourier map had a peak/hole in the vicinity of Sn1.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of Sn(C4H9)2(C18H12N2O3) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the butyl chains is not shown.

Crystal data

[Sn(C4H9)2(C18H12N2O3)]F(000) = 1096
Mr = 537.21Dx = 1.433 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4338 reflections
a = 11.6644 (9) Åθ = 2.2–21.2°
b = 17.2500 (14) ŵ = 1.05 mm1
c = 12.9296 (11) ÅT = 293 K
β = 106.793 (1)°Plate, orange
V = 2490.6 (4) Å30.40 × 0.40 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer4391 independent reflections
Radiation source: fine-focus sealed tube2953 reflections with I > 2σ(I)
graphiteRint = 0.038
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.678, Tmax = 0.902k = −20→20
19289 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0911P)2 + 4.703P] where P = (Fo2 + 2Fc2)/3
4391 reflections(Δ/σ)max = 0.001
314 parametersΔρmax = 1.19 e Å3
78 restraintsΔρmin = −1.14 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Sn10.23178 (5)0.55623 (3)0.50133 (4)0.0893 (3)
O10.2190 (5)0.4955 (4)0.6362 (5)0.1033 (17)
O20.3235 (5)0.6123 (3)0.4016 (4)0.0965 (16)
O30.6606 (4)0.8107 (3)0.2051 (3)0.0807 (13)
H30.60960.83440.15600.121*
N10.4181 (5)0.5601 (2)0.5908 (4)0.0602 (12)
N20.4920 (4)0.6041 (3)0.5446 (3)0.0602 (12)
C10.100 (2)0.6351 (12)0.4946 (19)0.145 (6)0.50
H1A0.07950.66120.42530.174*0.50
H1B0.02850.60800.49980.174*0.50
C20.1348 (19)0.6952 (16)0.584 (2)0.161 (7)0.50
H2A0.20070.72620.57520.193*0.50
H2B0.16110.66950.65360.193*0.50
C30.026 (2)0.7481 (16)0.5794 (19)0.188 (7)0.50
H3A0.01990.78900.52660.226*0.50
H3B−0.04770.71800.55850.226*0.50
C40.044 (3)0.7835 (19)0.693 (2)0.212 (9)0.50
H4A−0.02080.81820.69150.319*0.50
H4B0.11830.81140.71430.319*0.50
H4C0.04570.74270.74410.319*0.50
C50.143 (2)0.4749 (16)0.3952 (13)0.108 (5)0.50
H5A0.18200.42520.41690.130*0.50
H5B0.06250.47100.40080.130*0.50
C60.136 (2)0.4884 (13)0.2768 (13)0.134 (6)0.50
H6A0.21650.49070.26930.161*0.50
H6B0.09760.53780.25360.161*0.50
C70.066 (3)0.4238 (13)0.2044 (14)0.171 (7)0.50
H7A−0.01010.41560.21940.205*0.50
H7B0.11090.37580.21830.205*0.50
C80.044 (3)0.4484 (17)0.0853 (13)0.189 (7)0.50
H8A0.00440.40720.03870.284*0.50
H8B0.11960.45920.07230.284*0.50
H8C−0.00490.49410.07110.284*0.50
C1'0.157 (2)0.6678 (14)0.5198 (18)0.145 (6)0.50
H1'A0.21290.70770.51350.174*0.50
H1'B0.08420.67500.46060.174*0.50
C2'0.127 (2)0.6797 (14)0.6253 (18)0.161 (7)0.50
H2'A0.19570.66730.68570.193*0.50
H2'B0.06140.64570.62820.193*0.50
C3'0.090 (2)0.7660 (13)0.633 (3)0.188 (7)0.50
H3'A0.13500.78810.70120.226*0.50
H3'B0.10620.79600.57510.226*0.50
C4'−0.044 (2)0.7688 (18)0.622 (3)0.212 (9)0.50
H4'A−0.06770.82150.62770.319*0.50
H4'B−0.05960.73870.67920.319*0.50
H4'C−0.08820.74780.55370.319*0.50
C5'0.175 (2)0.4609 (16)0.3742 (15)0.108 (5)0.50
H5'A0.24170.44260.35070.130*0.50
H5'B0.13870.41750.40090.130*0.50
C6'0.082 (2)0.5037 (12)0.2830 (16)0.134 (6)0.50
H6'A0.02440.52920.31220.161*0.50
H6'B0.12270.54330.25300.161*0.50
C7'0.0180 (18)0.4479 (17)0.1940 (18)0.171 (7)0.50
H7'A−0.04410.47540.14040.205*0.50
H7'B−0.01960.40720.22440.205*0.50
C8'0.107 (3)0.4120 (18)0.140 (2)0.189 (7)0.50
H8'A0.06530.37600.08520.284*0.50
H8'B0.16870.38520.19320.284*0.50
H8'C0.14180.45220.10770.284*0.50
C90.2968 (7)0.4704 (4)0.7234 (6)0.0758 (18)
C100.2491 (8)0.4253 (5)0.7944 (7)0.095 (2)
H100.16720.41590.77640.114*
C110.3217 (8)0.3965 (4)0.8869 (7)0.095 (2)
H110.28800.36870.93240.113*
C120.4480 (7)0.4071 (4)0.9177 (5)0.0766 (19)
C130.5209 (9)0.3732 (4)1.0119 (6)0.093 (2)
H130.48610.34511.05640.111*
C140.6389 (10)0.3806 (5)1.0389 (6)0.104 (3)
H140.68680.35831.10220.124*
C150.6900 (9)0.4220 (6)0.9718 (7)0.108 (3)
H150.77280.42690.99060.130*
C160.6221 (8)0.4556 (4)0.8790 (6)0.086 (2)
H160.65910.48290.83550.104*
C170.4985 (7)0.4495 (3)0.8489 (5)0.0700 (17)
C180.4202 (6)0.4832 (3)0.7504 (5)0.0631 (15)
C190.4717 (6)0.5285 (3)0.6834 (5)0.0628 (15)
H190.55390.53640.70890.075*
C200.4327 (6)0.6281 (3)0.4476 (4)0.0617 (14)
C210.4956 (5)0.6762 (3)0.3855 (4)0.0553 (13)
C220.6181 (6)0.6895 (4)0.4194 (5)0.0657 (15)
H220.66440.66780.48370.079*
C230.6716 (6)0.7344 (4)0.3589 (5)0.0722 (17)
H230.75380.74280.38280.087*
C240.6044 (5)0.7675 (3)0.2624 (4)0.0607 (14)
C250.4824 (6)0.7539 (3)0.2282 (4)0.0669 (15)
H250.43590.77490.16340.080*
C260.4297 (6)0.7091 (3)0.2900 (4)0.0636 (14)
H260.34740.70100.26650.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0800 (4)0.0953 (4)0.0957 (4)0.0001 (3)0.0303 (3)0.0250 (3)
O10.082 (3)0.131 (5)0.105 (4)−0.013 (3)0.038 (3)0.027 (4)
O20.089 (3)0.117 (4)0.073 (3)−0.031 (3)0.008 (3)0.024 (3)
O30.083 (3)0.100 (3)0.067 (3)−0.003 (3)0.034 (2)0.021 (2)
N10.080 (3)0.054 (3)0.054 (3)−0.003 (2)0.031 (2)−0.001 (2)
N20.082 (3)0.057 (3)0.047 (2)−0.004 (2)0.028 (2)−0.001 (2)
C10.141 (10)0.149 (9)0.148 (8)−0.011 (7)0.046 (8)0.008 (7)
C20.173 (9)0.149 (10)0.161 (11)0.008 (7)0.048 (8)−0.004 (8)
C30.172 (11)0.193 (11)0.200 (10)0.023 (8)0.055 (9)−0.012 (8)
C40.200 (13)0.208 (12)0.223 (11)0.026 (9)0.052 (9)−0.035 (9)
C50.091 (9)0.109 (8)0.118 (6)−0.023 (7)0.019 (6)0.010 (6)
C60.129 (11)0.142 (8)0.134 (6)0.006 (8)0.043 (7)0.007 (6)
C70.168 (12)0.181 (10)0.154 (7)0.003 (9)0.032 (8)−0.016 (7)
C80.191 (12)0.194 (12)0.168 (8)−0.011 (9)0.030 (8)−0.001 (8)
C1'0.141 (10)0.149 (9)0.148 (8)−0.011 (7)0.046 (8)0.008 (7)
C2'0.173 (9)0.149 (10)0.161 (11)0.008 (7)0.048 (8)−0.004 (8)
C3'0.172 (11)0.193 (11)0.200 (10)0.023 (8)0.055 (9)−0.012 (8)
C4'0.200 (13)0.208 (12)0.223 (11)0.026 (9)0.052 (9)−0.035 (9)
C5'0.091 (9)0.109 (8)0.118 (6)−0.023 (7)0.019 (6)0.010 (6)
C6'0.129 (11)0.142 (8)0.134 (6)0.006 (8)0.043 (7)0.007 (6)
C7'0.168 (12)0.181 (10)0.154 (7)0.003 (9)0.032 (8)−0.016 (7)
C8'0.191 (12)0.194 (12)0.168 (8)−0.011 (9)0.030 (8)−0.001 (8)
C90.089 (5)0.073 (4)0.076 (4)0.001 (4)0.041 (4)0.007 (3)
C100.102 (6)0.100 (5)0.100 (6)−0.004 (4)0.058 (5)0.017 (4)
C110.128 (7)0.081 (5)0.097 (6)−0.002 (5)0.068 (5)0.016 (4)
C120.120 (6)0.056 (4)0.066 (4)0.008 (4)0.047 (4)0.005 (3)
C130.140 (8)0.074 (4)0.077 (5)0.009 (5)0.051 (5)0.014 (4)
C140.139 (8)0.097 (6)0.074 (5)0.014 (6)0.029 (5)0.030 (4)
C150.114 (7)0.122 (7)0.081 (5)0.003 (5)0.019 (5)0.024 (5)
C160.110 (6)0.081 (5)0.072 (4)−0.004 (4)0.031 (4)0.015 (3)
C170.105 (6)0.045 (3)0.071 (4)−0.001 (3)0.044 (4)−0.004 (3)
C180.094 (5)0.049 (3)0.058 (3)−0.001 (3)0.040 (3)−0.004 (3)
C190.087 (4)0.051 (3)0.058 (3)0.001 (3)0.033 (3)−0.001 (3)
C200.077 (4)0.053 (3)0.054 (3)−0.002 (3)0.019 (3)−0.005 (3)
C210.078 (4)0.046 (3)0.044 (3)−0.003 (3)0.020 (3)−0.005 (2)
C220.070 (4)0.077 (4)0.052 (3)0.008 (3)0.020 (3)0.010 (3)
C230.070 (4)0.090 (4)0.060 (3)0.004 (3)0.023 (3)0.014 (3)
C240.074 (4)0.063 (3)0.051 (3)0.002 (3)0.026 (3)0.000 (3)
C250.088 (5)0.063 (3)0.047 (3)−0.002 (3)0.015 (3)0.006 (3)
C260.071 (4)0.065 (3)0.053 (3)−0.008 (3)0.014 (3)−0.001 (3)

Geometric parameters (Å, °)

Sn1—C52.02 (2)C3'—H3'B0.9700
Sn1—C12.04 (2)C4'—H4'A0.9600
Sn1—O12.076 (5)C4'—H4'B0.9600
Sn1—O22.131 (5)C4'—H4'C0.9600
Sn1—N12.148 (5)C5'—C6'1.536 (10)
Sn1—C1'2.16 (2)C5'—H5'A0.9700
Sn1—C5'2.28 (2)C5'—H5'B0.9700
O1—C91.301 (8)C6'—C7'1.522 (10)
O2—C201.270 (7)C6'—H6'A0.9700
O3—C241.348 (7)C6'—H6'B0.9700
O3—H30.8400C7'—C8'1.537 (10)
N1—C191.300 (7)C7'—H7'A0.9700
N1—N21.404 (6)C7'—H7'B0.9700
N2—C201.312 (7)C8'—H8'A0.9600
C1—C21.518 (10)C8'—H8'B0.9600
C1—H1A0.9700C8'—H8'C0.9600
C1—H1B0.9700C9—C181.397 (10)
C2—C31.554 (10)C9—C101.433 (10)
C2—H2A0.9700C10—C111.344 (11)
C2—H2B0.9700C10—H100.9300
C3—C41.549 (10)C11—C121.422 (11)
C3—H3A0.9700C11—H110.9300
C3—H3B0.9700C12—C131.396 (10)
C4—H4A0.9600C12—C171.407 (9)
C4—H4B0.9600C13—C141.325 (12)
C4—H4C0.9600C13—H130.9300
C5—C61.526 (10)C14—C151.384 (12)
C5—H5A0.9700C14—H140.9300
C5—H5B0.9700C15—C161.362 (11)
C6—C71.532 (10)C15—H150.9300
C6—H6A0.9700C16—C171.384 (11)
C6—H6B0.9700C16—H160.9300
C7—C81.546 (10)C17—C181.457 (9)
C7—H7A0.9700C18—C191.422 (8)
C7—H7B0.9700C19—H190.9300
C8—H8A0.9600C20—C211.488 (8)
C8—H8B0.9600C21—C261.375 (8)
C8—H8C0.9600C21—C221.387 (8)
C1'—C2'1.517 (10)C22—C231.372 (8)
C1'—H1'A0.9700C22—H220.9300
C1'—H1'B0.9700C23—C241.390 (8)
C2'—C3'1.562 (10)C23—H230.9300
C2'—H2'A0.9700C24—C251.383 (9)
C2'—H2'B0.9700C25—C261.377 (8)
C3'—C4'1.523 (10)C25—H250.9300
C3'—H3'A0.9700C26—H260.9300
C5—Sn1—C1101.7 (10)C4'—C3'—H3'A110.0
C5—Sn1—O194.2 (6)C2'—C3'—H3'A110.0
C1—Sn1—O197.8 (7)C4'—C3'—H3'B110.0
C5—Sn1—O298.7 (6)C2'—C3'—H3'B110.0
C1—Sn1—O2100.2 (8)H3'A—C3'—H3'B108.4
O1—Sn1—O2155.2 (2)C3'—C4'—H4'A109.5
C5—Sn1—N1128.7 (7)C3'—C4'—H4'B109.5
C1—Sn1—N1129.6 (6)H4'A—C4'—H4'B109.5
O1—Sn1—N182.56 (19)C3'—C4'—H4'C109.5
O2—Sn1—N172.85 (18)H4'A—C4'—H4'C109.5
C5—Sn1—C1'123.4 (10)H4'B—C4'—H4'C109.5
C1—Sn1—C1'23.5 (8)C6'—C5'—Sn1101.6 (13)
O1—Sn1—C1'103.1 (6)C6'—C5'—H5'A111.5
O2—Sn1—C1'87.3 (6)Sn1—C5'—H5'A111.5
N1—Sn1—C1'107.0 (7)C6'—C5'—H5'B111.5
C5—Sn1—C5'13.5 (11)Sn1—C5'—H5'B111.5
C1—Sn1—C5'112.9 (8)H5'A—C5'—H5'B109.3
O1—Sn1—C5'99.5 (6)C7'—C6'—C5'111.1 (9)
O2—Sn1—C5'89.1 (7)C7'—C6'—H6'A109.4
N1—Sn1—C5'116.7 (6)C5'—C6'—H6'A109.4
C1'—Sn1—C5'132.7 (9)C7'—C6'—H6'B109.4
C9—O1—Sn1134.0 (4)C5'—C6'—H6'B109.4
C20—O2—Sn1115.1 (4)H6'A—C6'—H6'B108.0
C24—O3—H3109.5C6'—C7'—C8'110.4 (10)
C19—N1—N2115.3 (5)C6'—C7'—H7'A109.6
C19—N1—Sn1128.7 (4)C8'—C7'—H7'A109.6
N2—N1—Sn1116.0 (3)C6'—C7'—H7'B109.6
C20—N2—N1111.0 (5)C8'—C7'—H7'B109.6
C2—C1—Sn1112.8 (13)H7'A—C7'—H7'B108.1
C2—C1—H1A109.0C7'—C8'—H8'A109.5
Sn1—C1—H1A109.0C7'—C8'—H8'B109.5
C2—C1—H1B109.0H8'A—C8'—H8'B109.5
Sn1—C1—H1B109.0C7'—C8'—H8'C109.5
H1A—C1—H1B107.8H8'A—C8'—H8'C109.5
C1—C2—C3109.5 (10)H8'B—C8'—H8'C109.5
C1—C2—H2A109.8O1—C9—C18125.0 (6)
C3—C2—H2A109.8O1—C9—C10115.7 (7)
C1—C2—H2B109.8C18—C9—C10119.3 (7)
C3—C2—H2B109.8C11—C10—C9120.5 (8)
H2A—C2—H2B108.2C11—C10—H10119.7
C4—C3—C2108.0 (9)C9—C10—H10119.7
C4—C3—H3A110.1C10—C11—C12122.5 (7)
C2—C3—H3A110.1C10—C11—H11118.7
C4—C3—H3B110.1C12—C11—H11118.7
C2—C3—H3B110.1C13—C12—C11120.8 (7)
H3A—C3—H3B108.4C13—C12—C17120.6 (8)
C3—C4—H4A109.5C11—C12—C17118.6 (7)
C3—C4—H4B109.5C14—C13—C12120.9 (7)
H4A—C4—H4B109.5C14—C13—H13119.5
C3—C4—H4C109.5C12—C13—H13119.5
H4A—C4—H4C109.5C13—C14—C15119.2 (8)
H4B—C4—H4C109.5C13—C14—H14120.4
C6—C5—Sn1116.3 (13)C15—C14—H14120.4
C6—C5—H5A108.2C16—C15—C14121.7 (10)
Sn1—C5—H5A108.2C16—C15—H15119.2
C6—C5—H5B108.2C14—C15—H15119.2
Sn1—C5—H5B108.2C15—C16—C17120.6 (7)
H5A—C5—H5B107.4C15—C16—H16119.7
C5—C6—C7111.4 (10)C17—C16—H16119.7
C5—C6—H6A109.3C16—C17—C12117.0 (7)
C7—C6—H6A109.3C16—C17—C18123.7 (6)
C5—C6—H6B109.3C12—C17—C18119.3 (7)
C7—C6—H6B109.3C9—C18—C19121.4 (6)
H6A—C6—H6B108.0C9—C18—C17119.7 (6)
C6—C7—C8108.3 (9)C19—C18—C17118.9 (6)
C6—C7—H7A110.0N1—C19—C18128.1 (6)
C8—C7—H7A110.0N1—C19—H19116.0
C6—C7—H7B110.0C18—C19—H19116.0
C8—C7—H7B110.0O2—C20—N2124.1 (6)
H7A—C7—H7B108.4O2—C20—C21116.8 (5)
C7—C8—H8A109.5N2—C20—C21119.1 (5)
C7—C8—H8B109.5C26—C21—C22118.2 (5)
H8A—C8—H8B109.5C26—C21—C20118.7 (5)
C7—C8—H8C109.5C22—C21—C20123.0 (5)
H8A—C8—H8C109.5C23—C22—C21120.7 (5)
H8B—C8—H8C109.5C23—C22—H22119.7
C2'—C1'—Sn1115.2 (14)C21—C22—H22119.7
C2'—C1'—H1'A108.5C22—C23—C24120.8 (6)
Sn1—C1'—H1'A108.5C22—C23—H23119.6
C2'—C1'—H1'B108.5C24—C23—H23119.6
Sn1—C1'—H1'B108.5O3—C24—C25122.5 (5)
H1'A—C1'—H1'B107.5O3—C24—C23118.9 (6)
C1'—C2'—C3'108.8 (10)C25—C24—C23118.6 (5)
C1'—C2'—H2'A109.9C26—C25—C24120.0 (5)
C3'—C2'—H2'A109.9C26—C25—H25120.0
C1'—C2'—H2'B109.9C24—C25—H25120.0
C3'—C2'—H2'B109.9C21—C26—C25121.7 (6)
H2'A—C2'—H2'B108.3C21—C26—H26119.1
C4'—C3'—C2'108.5 (10)C25—C26—H26119.1
C5—Sn1—O1—C9123.5 (10)O2—Sn1—C5'—C6'−71.1 (14)
C1—Sn1—O1—C9−134.0 (9)N1—Sn1—C5'—C6'−141.4 (13)
O2—Sn1—O1—C92.1 (11)C1'—Sn1—C5'—C6'14 (2)
N1—Sn1—O1—C9−4.9 (7)Sn1—C5'—C6'—C7'−172.0 (14)
C1'—Sn1—O1—C9−110.7 (10)C5'—C6'—C7'—C8'−64 (3)
C5'—Sn1—O1—C9111.0 (9)Sn1—O1—C9—C183.2 (12)
C5—Sn1—O2—C20−136.3 (9)Sn1—O1—C9—C10−175.8 (5)
C1—Sn1—O2—C20120.0 (8)O1—C9—C10—C11−180.0 (7)
O1—Sn1—O2—C20−15.7 (9)C18—C9—C10—C111.0 (11)
N1—Sn1—O2—C20−8.4 (5)C9—C10—C11—C12−1.7 (12)
C1'—Sn1—O2—C20100.3 (8)C10—C11—C12—C13−177.0 (7)
C5'—Sn1—O2—C20−126.8 (7)C10—C11—C12—C170.2 (11)
C5—Sn1—N1—C19−86.0 (9)C11—C12—C13—C14177.6 (8)
C1—Sn1—N1—C1997.4 (11)C17—C12—C13—C140.3 (11)
O1—Sn1—N1—C193.5 (5)C12—C13—C14—C15−0.6 (13)
O2—Sn1—N1—C19−173.4 (5)C13—C14—C15—C160.4 (14)
C1'—Sn1—N1—C19105.0 (8)C14—C15—C16—C170.1 (13)
C5'—Sn1—N1—C19−93.4 (8)C15—C16—C17—C12−0.4 (10)
C5—Sn1—N1—N295.5 (8)C15—C16—C17—C18−179.4 (7)
C1—Sn1—N1—N2−81.1 (10)C13—C12—C17—C160.1 (9)
O1—Sn1—N1—N2−175.0 (4)C11—C12—C17—C16−177.2 (6)
O2—Sn1—N1—N28.1 (3)C13—C12—C17—C18179.2 (6)
C1'—Sn1—N1—N2−73.5 (7)C11—C12—C17—C181.9 (9)
C5'—Sn1—N1—N288.1 (8)O1—C9—C18—C192.0 (10)
C19—N1—N2—C20174.5 (5)C10—C9—C18—C19−179.1 (6)
Sn1—N1—N2—C20−6.8 (5)O1—C9—C18—C17−177.8 (6)
C5—Sn1—C1—C2168 (2)C10—C9—C18—C171.2 (9)
O1—Sn1—C1—C272 (2)C16—C17—C18—C9176.4 (6)
O2—Sn1—C1—C2−91 (2)C12—C17—C18—C9−2.6 (8)
N1—Sn1—C1—C2−14 (2)C16—C17—C18—C19−3.4 (9)
C1'—Sn1—C1—C2−33 (2)C12—C17—C18—C19177.7 (5)
C5'—Sn1—C1—C2176.1 (19)N2—N1—C19—C18177.9 (5)
Sn1—C1—C2—C3−175 (2)Sn1—N1—C19—C18−0.6 (8)
C1—C2—C3—C4156 (3)C9—C18—C19—N1−3.2 (9)
C1—Sn1—C5—C686.3 (19)C17—C18—C19—N1176.6 (5)
O1—Sn1—C5—C6−174.9 (17)Sn1—O2—C20—N28.3 (8)
O2—Sn1—C5—C6−16.1 (19)Sn1—O2—C20—C21−172.3 (4)
N1—Sn1—C5—C6−91.0 (18)N1—N2—C20—O2−1.0 (8)
C1'—Sn1—C5—C676 (2)N1—N2—C20—C21179.6 (4)
C5'—Sn1—C5—C6−61 (4)O2—C20—C21—C268.6 (8)
Sn1—C5—C6—C7−179 (2)N2—C20—C21—C26−172.0 (5)
C5—C6—C7—C8171 (3)O2—C20—C21—C22−171.4 (6)
C5—Sn1—C1'—C2'110 (2)N2—C20—C21—C228.0 (8)
C1—Sn1—C1'—C2'85 (3)C26—C21—C22—C230.0 (9)
O1—Sn1—C1'—C2'6(2)C20—C21—C22—C23−179.9 (5)
O2—Sn1—C1'—C2'−151 (2)C21—C22—C23—C24−0.1 (9)
N1—Sn1—C1'—C2'−80 (2)C22—C23—C24—O3−179.5 (5)
C5'—Sn1—C1'—C2'123 (2)C22—C23—C24—C25−0.3 (9)
Sn1—C1'—C2'—C3'172.6 (15)O3—C24—C25—C26179.9 (5)
C1'—C2'—C3'—C4'111 (3)C23—C24—C25—C260.8 (9)
C5—Sn1—C5'—C6'64 (4)C22—C21—C26—C250.5 (8)
C1—Sn1—C5'—C6'29.6 (18)C20—C21—C26—C25−179.6 (5)
O1—Sn1—C5'—C6'132.2 (14)C24—C25—C26—C21−0.9 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N2i0.841.992.824 (6)177

Symmetry codes: (i) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5252).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cui, J.-C., Pan, Q.-X., Yin, H.-D. & Qiao, Y.-L. (2007). Acta Cryst. E63, o2633.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography