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

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ISSN: 2056-9890

8-Hy­dr­oxy-2-methyl­quinolinium tetra­chlorido(pyrazine-2-carboxyl­ato-κ2N1,O2)stannate(IV) methanol monosolvate

aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 1 August 2011; accepted 9 August 2011; online 17 August 2011)

In the title solvated salt, (C10H10NO)[SnCl4(C5H3N2O2)]·CH3OH, the SnIV atom is chelated by the N,O-bidentate pyrazine-2-carboxyl­ate ligand and four chloride ions, and shows a distorted octa­hedral SnNOCl4 coordination at the metal atom. The 8-hy­droxy-2-methyl­quinolinium cation and the anion are linked to the methanol mol­ecules by O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, generating a linear chain running along [1[\overline{1}]0]. There are two independent ion pairs and solvent mol­ecules in the asymmetric unit. The crystal studied was a non-merohedral twin with a 41.8 (1)% twin component.

Related literature

For another ammonium tetra­chlorido(pyrazine-2-carboxyl­ato)stannate(IV), see: Najafi et al. (2011[Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m238.]).

[Scheme 1]

Experimental

Crystal data
  • (C10H10NO)[SnCl4(C5H3N2O2)]·CH4O

  • Mr = 575.82

  • Triclinic, [P \overline 1]

  • a = 6.8392 (2) Å

  • b = 16.9759 (8) Å

  • c = 17.6637 (10) Å

  • α = 90.337 (4)°

  • β = 94.429 (4)°

  • γ = 92.232 (3)°

  • V = 2043.03 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.80 mm−1

  • T = 100 K

  • 0.25 × 0.25 × 0.10 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.661, Tmax = 0.840

  • 11717 measured reflections

  • 11717 independent reflections

  • 10323 reflections with I > 2σ(I)

  • Rint = 0.074

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.116

  • S = 1.08

  • 11717 reflections

  • 514 parameters

  • H-atom parameters constrained

  • Δρmax = 1.47 e Å−3

  • Δρmin = −1.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5o⋯O7 0.84 1.84 2.661 (5) 167
O7—H7o⋯N2 0.84 2.05 2.871 (5) 165
O6—H6o⋯O8 0.84 1.82 2.649 (5) 171
O8—H8o⋯N4 0.84 2.10 2.924 (5) 168
N5—H5n⋯O4 0.88 1.88 2.731 (5) 163
N6—H6n⋯O2i 0.88 1.98 2.838 (5) 164
Symmetry code: (i) x+1, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

In a recent study, we reacted stannic chloride with pyrazine-2-carboxylic acid in methanol, the reaction yielding the tetrachlorido(pyrazine-2-carbxoylato)stannate anion, whose charge was balanced by a 3-methoxycarbonyl-1-methylpyrazinium cation (Najafi et al., 2011). The cation was derived from the original carboxylic acid which was simultaneously esterified and N-methylated. A similar synthesis but with 2-methyl-8-hydroxyquinoline in methanol medium yielded the solvated title salt (Scheme I, Fig. 1). The less sterically crowded carboxylate ligand engages in chelation, and the more crowded quinoline ligand is protonated. The SnIV atom shows distorted octahedral SnNOCl4 coordination. The cation and anion are linked to the methanol molecules by O–H···O and N–H···O hydrogen bonds (Table 1). There are two independent ion-pairs and solvent molecules. The crystal studied is a non-merohedral twin with a 41.8 (1)% twin component.

Related literature top

For another ammonium tetrachlorido(pyrazine-2-carboxylato)stannate(IV), see: Najafi et al. (2011).

Experimental top

Stannic chloride pentahydrate (0.35 g, 1 mmol), pyrazine-2-carboxylic acid (0.13 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.16 g, 1 mmol) were loaded into a convection tube and the tube was filled with dry methanol and kept at 333 K. Colorless crystals were collected from the side arm after several days.

Refinement top

Carbon-, nitrogen- and oxygen-bound H-atoms were placed in calculated positions [C—H = 0.95 to 0.98 Å, N—H = 0.88 Å, O—H = 0.84 Å] and Uiso(H) = 1.2 to 1.5Ueq(C,N,O)] and were included in the refinement in the riding model approximation. The final difference Fourier map had a peak in the vicinity of Sn2 and a hole in the vicinity of Sn1. The crystal studied is a non-merohedral twin with a minor component of 41.8 (1)%.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (C10H10NO)[SnCl4(C5H3N2O2)].CH3OH, at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
8-Hydroxy-2-methylquinolinium tetrachlorido(pyrazine-2-carboxylato-κ2N1,O2)stannate(IV) methanol monosolvate top
Crystal data top
(C10H10NO)[SnCl4(C5H3N2O2)]·CH4OZ = 4
Mr = 575.82F(000) = 1136
Triclinic, P1Dx = 1.872 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8392 (2) ÅCell parameters from 4896 reflections
b = 16.9759 (8) Åθ = 2.3–27.5°
c = 17.6637 (10) ŵ = 1.80 mm1
α = 90.337 (4)°T = 100 K
β = 94.429 (4)°Prism, colorless
γ = 92.232 (3)°0.25 × 0.25 × 0.10 mm
V = 2043.03 (16) Å3
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
11717 independent reflections
Radiation source: SuperNova (Mo) X-ray Source10323 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.074
Detector resolution: 10.4041 pixels mm-1θmax = 27.5°, θmin = 2.3°
ω scansh = 88
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 2121
Tmin = 0.661, Tmax = 0.840l = 2222
11717 measured reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0698P)2]
where P = (Fo2 + 2Fc2)/3
11717 reflections(Δ/σ)max = 0.001
514 parametersΔρmax = 1.47 e Å3
0 restraintsΔρmin = 1.44 e Å3
Crystal data top
(C10H10NO)[SnCl4(C5H3N2O2)]·CH4Oγ = 92.232 (3)°
Mr = 575.82V = 2043.03 (16) Å3
Triclinic, P1Z = 4
a = 6.8392 (2) ÅMo Kα radiation
b = 16.9759 (8) ŵ = 1.80 mm1
c = 17.6637 (10) ÅT = 100 K
α = 90.337 (4)°0.25 × 0.25 × 0.10 mm
β = 94.429 (4)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
11717 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
10323 reflections with I > 2σ(I)
Tmin = 0.661, Tmax = 0.840Rint = 0.074
11717 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.08Δρmax = 1.47 e Å3
11717 reflectionsΔρmin = 1.44 e Å3
514 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.61697 (4)1.596168 (18)0.654851 (18)0.00792 (8)
Sn21.08405 (4)1.091896 (18)0.846561 (18)0.00807 (9)
Cl10.45746 (16)1.69944 (7)0.71191 (7)0.0121 (2)
Cl20.57579 (16)1.63204 (7)0.52408 (6)0.0136 (2)
Cl30.32606 (16)1.51100 (7)0.64196 (7)0.0123 (2)
Cl40.93371 (16)1.65961 (7)0.66605 (7)0.0158 (3)
Cl50.91591 (17)1.19680 (7)0.78769 (7)0.0137 (2)
Cl61.07721 (16)1.12849 (7)0.97661 (6)0.0127 (2)
Cl71.40092 (16)1.15454 (7)0.84076 (7)0.0140 (2)
Cl80.79318 (16)1.00802 (7)0.85129 (7)0.0133 (2)
O10.6790 (4)1.54266 (19)0.75974 (18)0.0112 (7)
O20.8132 (5)1.4405 (2)0.82093 (19)0.0158 (7)
O31.1240 (5)1.03584 (19)0.74318 (18)0.0118 (7)
O41.2544 (5)0.9339 (2)0.68656 (19)0.0171 (8)
O51.2786 (5)1.0859 (2)0.59595 (19)0.0154 (7)
H5O1.26151.13220.61030.023*
O61.8052 (5)0.5901 (2)0.92417 (19)0.0147 (7)
H6O1.81190.63750.91100.022*
O71.2839 (5)1.2368 (2)0.6382 (2)0.0228 (9)
H7O1.19521.26730.62350.034*
O81.7831 (5)0.7393 (2)0.8827 (2)0.0188 (8)
H8O1.68210.76470.88820.028*
N10.7781 (5)1.4869 (2)0.6269 (2)0.0089 (8)
N20.9857 (6)1.3506 (2)0.6162 (2)0.0134 (9)
N31.2494 (5)0.9823 (2)0.8807 (2)0.0081 (8)
N41.4662 (6)0.8481 (2)0.8964 (2)0.0138 (9)
N51.2367 (5)0.9428 (2)0.5319 (2)0.0094 (8)
H5N1.23720.95030.58120.011*
N61.7531 (5)0.4442 (2)0.9781 (2)0.0094 (8)
H6N1.77330.45340.93030.011*
C10.7736 (6)1.4772 (3)0.7640 (3)0.0092 (9)
C20.8332 (6)1.4461 (3)0.6889 (3)0.0099 (9)
C30.9371 (7)1.3782 (3)0.6833 (3)0.0136 (10)
H30.97501.35040.72820.016*
C40.9310 (6)1.3919 (3)0.5549 (3)0.0133 (10)
H40.96601.37450.50670.016*
C50.8231 (6)1.4605 (3)0.5591 (3)0.0098 (9)
H50.78231.48770.51420.012*
C61.2204 (7)0.9719 (3)0.7426 (3)0.0115 (9)
C71.2951 (6)0.9421 (3)0.8197 (3)0.0095 (9)
C81.4038 (7)0.8751 (3)0.8276 (3)0.0135 (10)
H81.43510.84760.78340.016*
C91.4166 (6)0.8884 (3)0.9566 (3)0.0130 (10)
H91.45710.87071.00600.016*
C101.3069 (7)0.9558 (3)0.9490 (3)0.0134 (10)
H101.27310.98290.99310.016*
C111.2567 (7)1.0078 (3)0.4856 (3)0.0099 (9)
C121.2771 (6)1.0836 (3)0.5197 (3)0.0112 (9)
C131.2956 (7)1.1475 (3)0.4735 (3)0.0132 (10)
H131.31161.19880.49530.016*
C141.2913 (7)1.1381 (3)0.3940 (3)0.0166 (11)
H141.30131.18330.36280.020*
C151.2730 (7)1.0648 (3)0.3611 (3)0.0177 (11)
H151.27301.05900.30760.021*
C161.2541 (6)0.9978 (3)0.4072 (3)0.0123 (10)
C171.2341 (7)0.9196 (3)0.3781 (3)0.0143 (10)
H171.23390.91040.32490.017*
C181.2155 (7)0.8578 (3)0.4256 (3)0.0143 (10)
H181.20140.80590.40510.017*
C191.2165 (6)0.8689 (3)0.5043 (3)0.0127 (10)
C201.1981 (7)0.8021 (3)0.5576 (3)0.0192 (11)
H20A1.20890.82230.60990.029*
H20B1.30280.76540.55110.029*
H20C1.07020.77450.54690.029*
C311.7444 (6)0.5077 (3)1.0259 (3)0.0093 (9)
C321.7685 (6)0.5861 (3)0.9984 (3)0.0109 (10)
C331.7570 (6)0.6482 (3)1.0467 (3)0.0123 (10)
H331.77250.70051.02860.015*
C341.7222 (7)0.6355 (3)1.1238 (3)0.0158 (10)
H341.71530.67941.15680.019*
C351.6983 (7)0.5611 (3)1.1512 (3)0.0142 (10)
H351.67450.55361.20300.017*
C361.7087 (6)0.4953 (3)1.1028 (3)0.0131 (10)
C371.6868 (7)0.4162 (3)1.1267 (3)0.0139 (10)
H371.66280.40541.17790.017*
C381.6998 (7)0.3554 (3)1.0765 (3)0.0130 (10)
H381.68660.30261.09350.016*
C391.7329 (6)0.3701 (3)0.9996 (3)0.0108 (9)
C401.7473 (7)0.3053 (3)0.9442 (3)0.0150 (10)
H40A1.79110.32700.89680.022*
H40B1.61840.27850.93420.022*
H40C1.84200.26770.96500.022*
C411.4473 (7)1.2813 (3)0.6720 (3)0.0219 (12)
H41A1.52131.30540.63210.033*
H41B1.53221.24670.70270.033*
H41C1.40161.32280.70440.033*
C421.9073 (7)0.7824 (3)0.8360 (3)0.0195 (11)
H42A1.95530.83130.86210.029*
H42B1.83370.79500.78810.029*
H42C2.01890.75060.82550.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.00955 (15)0.00599 (17)0.00853 (16)0.00151 (11)0.00198 (12)0.00095 (12)
Sn20.01070 (15)0.00607 (17)0.00769 (16)0.00190 (12)0.00154 (12)0.00014 (12)
Cl10.0160 (5)0.0070 (5)0.0141 (6)0.0036 (4)0.0042 (4)0.0003 (4)
Cl20.0179 (6)0.0132 (6)0.0101 (6)0.0026 (4)0.0025 (4)0.0033 (4)
Cl30.0113 (5)0.0116 (6)0.0140 (6)0.0030 (4)0.0019 (4)0.0006 (5)
Cl40.0114 (5)0.0141 (6)0.0220 (6)0.0019 (4)0.0028 (5)0.0015 (5)
Cl50.0175 (6)0.0092 (6)0.0141 (6)0.0045 (4)0.0019 (4)0.0010 (4)
Cl60.0172 (5)0.0124 (6)0.0089 (5)0.0023 (4)0.0025 (4)0.0028 (4)
Cl70.0117 (5)0.0130 (6)0.0175 (6)0.0013 (4)0.0022 (4)0.0026 (5)
Cl80.0120 (5)0.0139 (6)0.0139 (6)0.0019 (4)0.0015 (4)0.0010 (5)
O10.0144 (16)0.0110 (17)0.0087 (16)0.0055 (13)0.0004 (13)0.0032 (13)
O20.0200 (18)0.0168 (19)0.0111 (17)0.0054 (15)0.0016 (14)0.0061 (15)
O30.0176 (17)0.0092 (17)0.0087 (16)0.0024 (13)0.0009 (13)0.0034 (13)
O40.030 (2)0.0126 (19)0.0098 (17)0.0036 (15)0.0056 (15)0.0017 (14)
O50.0252 (19)0.0099 (18)0.0115 (17)0.0035 (15)0.0030 (15)0.0038 (14)
O60.0227 (18)0.0116 (18)0.0105 (17)0.0022 (15)0.0055 (14)0.0020 (14)
O70.0184 (18)0.015 (2)0.034 (2)0.0076 (15)0.0065 (17)0.0047 (17)
O80.024 (2)0.0103 (18)0.023 (2)0.0060 (15)0.0056 (16)0.0068 (15)
N10.0115 (19)0.0030 (19)0.012 (2)0.0017 (15)0.0021 (15)0.0001 (15)
N20.013 (2)0.008 (2)0.018 (2)0.0023 (16)0.0019 (17)0.0015 (17)
N30.0077 (18)0.0044 (19)0.0121 (19)0.0004 (14)0.0002 (15)0.0000 (15)
N40.0107 (19)0.012 (2)0.018 (2)0.0024 (16)0.0006 (16)0.0004 (17)
N50.0082 (18)0.010 (2)0.011 (2)0.0031 (15)0.0021 (15)0.0022 (16)
N60.0080 (18)0.009 (2)0.011 (2)0.0017 (15)0.0006 (15)0.0004 (16)
C10.010 (2)0.004 (2)0.013 (2)0.0035 (17)0.0013 (17)0.0001 (18)
C20.011 (2)0.008 (2)0.010 (2)0.0027 (18)0.0002 (18)0.0029 (18)
C30.014 (2)0.011 (2)0.016 (3)0.0020 (19)0.0033 (19)0.001 (2)
C40.009 (2)0.011 (2)0.020 (3)0.0015 (18)0.0024 (19)0.007 (2)
C50.014 (2)0.006 (2)0.010 (2)0.0031 (17)0.0034 (18)0.0021 (18)
C60.015 (2)0.008 (2)0.012 (2)0.0008 (18)0.0040 (18)0.0002 (18)
C70.011 (2)0.006 (2)0.011 (2)0.0035 (18)0.0031 (18)0.0013 (18)
C80.014 (2)0.011 (2)0.016 (2)0.0002 (18)0.0056 (19)0.005 (2)
C90.012 (2)0.012 (2)0.014 (2)0.0000 (18)0.0043 (18)0.005 (2)
C100.014 (2)0.016 (3)0.010 (2)0.0009 (19)0.0021 (18)0.0031 (19)
C110.0080 (19)0.007 (2)0.014 (2)0.0022 (17)0.0015 (18)0.0032 (19)
C120.005 (2)0.014 (2)0.015 (2)0.0025 (17)0.0041 (18)0.001 (2)
C130.014 (2)0.012 (2)0.014 (2)0.0013 (19)0.0013 (19)0.001 (2)
C140.018 (2)0.012 (2)0.020 (3)0.0015 (19)0.001 (2)0.010 (2)
C150.018 (2)0.021 (3)0.014 (3)0.000 (2)0.003 (2)0.005 (2)
C160.008 (2)0.016 (3)0.012 (2)0.0032 (18)0.0004 (18)0.001 (2)
C170.021 (3)0.014 (3)0.007 (2)0.006 (2)0.0059 (19)0.0059 (19)
C180.017 (2)0.011 (2)0.015 (2)0.0006 (19)0.0013 (19)0.004 (2)
C190.007 (2)0.011 (2)0.020 (3)0.0008 (18)0.0016 (19)0.001 (2)
C200.023 (3)0.017 (3)0.018 (3)0.003 (2)0.006 (2)0.001 (2)
C310.006 (2)0.007 (2)0.015 (2)0.0024 (17)0.0005 (18)0.0010 (19)
C320.007 (2)0.014 (2)0.013 (2)0.0034 (18)0.0024 (18)0.0045 (19)
C330.012 (2)0.009 (2)0.016 (2)0.0018 (18)0.0023 (19)0.0016 (19)
C340.013 (2)0.017 (3)0.018 (3)0.005 (2)0.001 (2)0.000 (2)
C350.012 (2)0.016 (3)0.015 (2)0.0011 (19)0.003 (2)0.003 (2)
C360.010 (2)0.014 (3)0.016 (2)0.0065 (18)0.0002 (18)0.002 (2)
C370.014 (2)0.017 (3)0.011 (2)0.001 (2)0.0028 (19)0.003 (2)
C380.013 (2)0.010 (2)0.017 (3)0.0024 (18)0.0040 (19)0.007 (2)
C390.009 (2)0.009 (2)0.015 (2)0.0004 (18)0.0016 (18)0.0017 (19)
C400.021 (3)0.006 (2)0.018 (3)0.0001 (19)0.001 (2)0.0026 (19)
C410.022 (3)0.022 (3)0.022 (3)0.001 (2)0.004 (2)0.002 (2)
C420.018 (2)0.022 (3)0.019 (3)0.000 (2)0.003 (2)0.003 (2)
Geometric parameters (Å, º) top
Sn1—O12.089 (3)C8—H80.9500
Sn1—N12.265 (4)C9—C101.393 (7)
Sn1—Cl12.3617 (11)C9—H90.9500
Sn1—Cl42.3752 (11)C10—H100.9500
Sn1—Cl22.3906 (12)C11—C161.392 (6)
Sn1—Cl32.4089 (11)C11—C121.416 (7)
Sn2—O32.096 (3)C12—C131.368 (7)
Sn2—N32.275 (4)C13—C141.410 (7)
Sn2—Cl52.3605 (12)C13—H130.9500
Sn2—Cl62.3806 (11)C14—C151.368 (7)
Sn2—Cl72.3862 (11)C14—H140.9500
Sn2—Cl82.4079 (11)C15—C161.409 (7)
O1—C11.308 (5)C15—H150.9500
O2—C11.205 (6)C16—C171.420 (7)
O3—C61.292 (6)C17—C181.355 (7)
O4—C61.221 (6)C17—H170.9500
O5—C121.347 (6)C18—C191.401 (7)
O5—H5O0.8400C18—H180.9500
O6—C321.356 (6)C19—C201.486 (7)
O6—H6O0.8400C20—H20A0.9800
O7—C411.415 (6)C20—H20B0.9800
O7—H7O0.8400C20—H20C0.9800
O8—C421.414 (6)C31—C361.413 (7)
O8—H8O0.8400C31—C321.426 (6)
N1—C21.337 (6)C32—C331.361 (7)
N1—C51.338 (6)C33—C341.415 (7)
N2—C41.330 (6)C33—H330.9500
N2—C31.342 (6)C34—C351.363 (7)
N3—C101.327 (6)C34—H340.9500
N3—C71.336 (6)C35—C361.411 (7)
N4—C91.334 (6)C35—H350.9500
N4—C81.346 (6)C36—C371.415 (7)
N5—C191.341 (6)C37—C381.367 (7)
N5—C111.387 (6)C37—H370.9500
N5—H5N0.8800C38—C391.416 (6)
N6—C391.322 (6)C38—H380.9500
N6—C311.372 (6)C39—C401.478 (6)
N6—H6N0.8800C40—H40A0.9800
C1—C21.515 (6)C40—H40B0.9800
C2—C31.384 (6)C40—H40C0.9800
C3—H30.9500C41—H41A0.9800
C4—C51.407 (6)C41—H41B0.9800
C4—H40.9500C41—H41C0.9800
C5—H50.9500C42—H42A0.9800
C6—C71.515 (6)C42—H42B0.9800
C7—C81.385 (6)C42—H42C0.9800
O1—Sn1—N175.54 (13)C9—C10—H10119.8
O1—Sn1—Cl191.69 (9)N5—C11—C16120.1 (4)
N1—Sn1—Cl1167.23 (10)N5—C11—C12118.6 (4)
O1—Sn1—Cl489.55 (9)C16—C11—C12121.3 (4)
N1—Sn1—Cl484.94 (10)O5—C12—C13125.8 (5)
Cl1—Sn1—Cl495.50 (4)O5—C12—C11116.0 (4)
O1—Sn1—Cl2167.42 (9)C13—C12—C11118.2 (4)
N1—Sn1—Cl291.93 (10)C12—C13—C14121.0 (5)
Cl1—Sn1—Cl2100.83 (4)C12—C13—H13119.5
Cl4—Sn1—Cl290.47 (4)C14—C13—H13119.5
O1—Sn1—Cl386.50 (9)C15—C14—C13120.8 (5)
N1—Sn1—Cl385.21 (10)C15—C14—H14119.6
Cl1—Sn1—Cl393.76 (4)C13—C14—H14119.6
Cl4—Sn1—Cl3170.03 (4)C14—C15—C16119.6 (5)
Cl2—Sn1—Cl391.41 (4)C14—C15—H15120.2
O3—Sn2—N375.79 (13)C16—C15—H15120.2
O3—Sn2—Cl593.46 (10)C11—C16—C15119.2 (5)
N3—Sn2—Cl5169.25 (10)C11—C16—C17117.4 (4)
O3—Sn2—Cl6166.10 (10)C15—C16—C17123.4 (5)
N3—Sn2—Cl690.32 (10)C18—C17—C16120.4 (4)
Cl5—Sn2—Cl6100.43 (4)C18—C17—H17119.8
O3—Sn2—Cl788.23 (9)C16—C17—H17119.8
N3—Sn2—Cl785.53 (10)C17—C18—C19121.5 (5)
Cl5—Sn2—Cl794.30 (4)C17—C18—H18119.3
Cl6—Sn2—Cl791.27 (4)C19—C18—H18119.3
O3—Sn2—Cl886.55 (9)N5—C19—C18118.1 (5)
N3—Sn2—Cl885.19 (10)N5—C19—C20119.4 (5)
Cl5—Sn2—Cl894.26 (4)C18—C19—C20122.5 (5)
Cl6—Sn2—Cl891.82 (4)C19—C20—H20A109.5
Cl7—Sn2—Cl8170.23 (4)C19—C20—H20B109.5
C1—O1—Sn1120.4 (3)H20A—C20—H20B109.5
C6—O3—Sn2119.9 (3)C19—C20—H20C109.5
C12—O5—H5O109.5H20A—C20—H20C109.5
C32—O6—H6O109.5H20B—C20—H20C109.5
C41—O7—H7O109.5N6—C31—C36119.6 (4)
C42—O8—H8O109.5N6—C31—C32120.5 (4)
C2—N1—C5118.8 (4)C36—C31—C32119.9 (4)
C2—N1—Sn1112.3 (3)O6—C32—C33126.4 (5)
C5—N1—Sn1128.9 (3)O6—C32—C31114.2 (4)
C4—N2—C3117.0 (4)C33—C32—C31119.5 (4)
C10—N3—C7118.6 (4)C32—C33—C34120.5 (5)
C10—N3—Sn2130.2 (3)C32—C33—H33119.8
C7—N3—Sn2111.2 (3)C34—C33—H33119.8
C9—N4—C8116.8 (4)C35—C34—C33121.0 (5)
C19—N5—C11122.5 (4)C35—C34—H34119.5
C19—N5—H5N118.8C33—C34—H34119.5
C11—N5—H5N118.8C34—C35—C36120.1 (5)
C39—N6—C31123.9 (4)C34—C35—H35119.9
C39—N6—H6N118.1C36—C35—H35119.9
C31—N6—H6N118.1C35—C36—C31119.0 (5)
O2—C1—O1126.0 (4)C35—C36—C37123.7 (5)
O2—C1—C2119.0 (4)C31—C36—C37117.2 (4)
O1—C1—C2115.0 (4)C38—C37—C36120.4 (4)
N1—C2—C3120.7 (4)C38—C37—H37119.8
N1—C2—C1116.8 (4)C36—C37—H37119.8
C3—C2—C1122.6 (4)C37—C38—C39120.9 (5)
N2—C3—C2121.9 (5)C37—C38—H38119.6
N2—C3—H3119.1C39—C38—H38119.6
C2—C3—H3119.1N6—C39—C38118.0 (4)
N2—C4—C5122.1 (5)N6—C39—C40120.0 (4)
N2—C4—H4118.9C38—C39—C40121.9 (4)
C5—C4—H4118.9C39—C40—H40A109.5
N1—C5—C4119.6 (5)C39—C40—H40B109.5
N1—C5—H5120.2H40A—C40—H40B109.5
C4—C5—H5120.2C39—C40—H40C109.5
O4—C6—O3126.4 (5)H40A—C40—H40C109.5
O4—C6—C7118.0 (4)H40B—C40—H40C109.5
O3—C6—C7115.6 (4)O7—C41—H41A109.5
N3—C7—C8120.7 (4)O7—C41—H41B109.5
N3—C7—C6117.4 (4)H41A—C41—H41B109.5
C8—C7—C6121.9 (4)O7—C41—H41C109.5
N4—C8—C7121.5 (4)H41A—C41—H41C109.5
N4—C8—H8119.2H41B—C41—H41C109.5
C7—C8—H8119.2O8—C42—H42A109.5
N4—C9—C10121.9 (5)O8—C42—H42B109.5
N4—C9—H9119.0H42A—C42—H42B109.5
C10—C9—H9119.0O8—C42—H42C109.5
N3—C10—C9120.4 (4)H42A—C42—H42C109.5
N3—C10—H10119.8H42B—C42—H42C109.5
N1—Sn1—O1—C10.3 (3)O4—C6—C7—C81.8 (7)
Cl1—Sn1—O1—C1179.9 (3)O3—C6—C7—C8178.8 (4)
Cl4—Sn1—O1—C184.6 (3)C9—N4—C8—C70.7 (7)
Cl2—Sn1—O1—C15.5 (7)N3—C7—C8—N40.3 (7)
Cl3—Sn1—O1—C186.3 (3)C6—C7—C8—N4178.6 (4)
N3—Sn2—O3—C62.2 (3)C8—N4—C9—C100.6 (7)
Cl5—Sn2—O3—C6177.8 (3)C7—N3—C10—C91.5 (7)
Cl6—Sn2—O3—C64.5 (6)Sn2—N3—C10—C9176.7 (3)
Cl7—Sn2—O3—C683.6 (3)N4—C9—C10—N30.5 (7)
Cl8—Sn2—O3—C688.2 (3)C19—N5—C11—C160.8 (6)
O1—Sn1—N1—C21.4 (3)C19—N5—C11—C12180.0 (4)
Cl1—Sn1—N1—C23.1 (7)N5—C11—C12—O51.1 (6)
Cl4—Sn1—N1—C289.5 (3)C16—C11—C12—O5179.7 (4)
Cl2—Sn1—N1—C2179.8 (3)N5—C11—C12—C13179.6 (4)
Cl3—Sn1—N1—C289.0 (3)C16—C11—C12—C130.4 (7)
O1—Sn1—N1—C5179.1 (4)O5—C12—C13—C14179.8 (4)
Cl1—Sn1—N1—C5177.3 (3)C11—C12—C13—C141.0 (7)
Cl4—Sn1—N1—C590.1 (4)C12—C13—C14—C151.5 (7)
Cl2—Sn1—N1—C50.2 (4)C13—C14—C15—C161.3 (7)
Cl3—Sn1—N1—C591.5 (4)N5—C11—C16—C15179.5 (4)
O3—Sn2—N3—C10178.4 (4)C12—C11—C16—C150.3 (7)
Cl5—Sn2—N3—C10178.3 (4)N5—C11—C16—C171.2 (6)
Cl6—Sn2—N3—C101.0 (4)C12—C11—C16—C17179.6 (4)
Cl7—Sn2—N3—C1092.3 (4)C14—C15—C16—C110.7 (7)
Cl8—Sn2—N3—C1090.8 (4)C14—C15—C16—C17179.9 (5)
O3—Sn2—N3—C73.3 (3)C11—C16—C17—C181.0 (7)
Cl5—Sn2—N3—C73.4 (7)C15—C16—C17—C18179.6 (5)
Cl6—Sn2—N3—C7177.3 (3)C16—C17—C18—C190.4 (7)
Cl7—Sn2—N3—C786.0 (3)C11—N5—C19—C180.2 (6)
Cl8—Sn2—N3—C790.9 (3)C11—N5—C19—C20179.3 (4)
Sn1—O1—C1—O2178.2 (4)C17—C18—C19—N50.0 (7)
Sn1—O1—C1—C20.7 (5)C17—C18—C19—C20179.5 (5)
C5—N1—C2—C30.8 (7)C39—N6—C31—C361.1 (7)
Sn1—N1—C2—C3178.7 (3)C39—N6—C31—C32179.7 (4)
C5—N1—C2—C1178.2 (4)N6—C31—C32—O61.9 (6)
Sn1—N1—C2—C12.2 (5)C36—C31—C32—O6178.9 (4)
O2—C1—C2—N1177.0 (4)N6—C31—C32—C33179.3 (4)
O1—C1—C2—N12.0 (6)C36—C31—C32—C330.1 (7)
O2—C1—C2—C32.1 (7)O6—C32—C33—C34178.5 (4)
O1—C1—C2—C3178.9 (4)C31—C32—C33—C340.2 (7)
C4—N2—C3—C20.6 (7)C32—C33—C34—C350.4 (7)
N1—C2—C3—N20.3 (7)C33—C34—C35—C360.2 (7)
C1—C2—C3—N2178.8 (4)C34—C35—C36—C310.1 (7)
C3—N2—C4—C51.5 (7)C34—C35—C36—C37179.6 (4)
C2—N1—C5—C41.7 (6)N6—C31—C36—C35179.4 (4)
Sn1—N1—C5—C4177.8 (3)C32—C31—C36—C350.2 (7)
N2—C4—C5—N12.1 (7)N6—C31—C36—C371.0 (6)
Sn2—O3—C6—O4179.7 (4)C32—C31—C36—C37179.8 (4)
Sn2—O3—C6—C70.9 (5)C35—C36—C37—C38179.6 (4)
C10—N3—C7—C81.4 (6)C31—C36—C37—C380.1 (7)
Sn2—N3—C7—C8177.1 (3)C36—C37—C38—C390.8 (7)
C10—N3—C7—C6177.6 (4)C31—N6—C39—C380.2 (6)
Sn2—N3—C7—C63.9 (5)C31—N6—C39—C40179.1 (4)
O4—C6—C7—N3177.1 (4)C37—C38—C39—N60.8 (7)
O3—C6—C7—N32.3 (6)C37—C38—C39—C40179.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5o···O70.841.842.661 (5)167
O7—H7o···N20.842.052.871 (5)165
O6—H6o···O80.841.822.649 (5)171
O8—H8o···N40.842.102.924 (5)168
N5—H5n···O40.881.882.731 (5)163
N6—H6n···O2i0.881.982.838 (5)164
Symmetry code: (i) x+1, y1, z.

Experimental details

Crystal data
Chemical formula(C10H10NO)[SnCl4(C5H3N2O2)]·CH4O
Mr575.82
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)6.8392 (2), 16.9759 (8), 17.6637 (10)
α, β, γ (°)90.337 (4), 94.429 (4), 92.232 (3)
V3)2043.03 (16)
Z4
Radiation typeMo Kα
µ (mm1)1.80
Crystal size (mm)0.25 × 0.25 × 0.10
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.661, 0.840
No. of measured, independent and
observed [I > 2σ(I)] reflections
11717, 11717, 10323
Rint0.074
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.116, 1.08
No. of reflections11717
No. of parameters514
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.47, 1.44

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5o···O70.841.842.661 (5)167
O7—H7o···N20.842.052.871 (5)165
O6—H6o···O80.841.822.649 (5)171
O8—H8o···N40.842.102.924 (5)168
N5—H5n···O40.881.882.731 (5)163
N6—H6n···O2i0.881.982.838 (5)164
Symmetry code: (i) x+1, y1, z.
 

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationNajafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m238.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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