Dichlorido{1-[N-(5-chloro-2-oxidophen­yl)carboximido­yl]naphthalen-2-olato-κ3O,N,O′}(methanol-κO)tin(IV)

Shahverdizadeh, G.H.; Ng, S.W.; Tiekink, E.R.T.; Mirtamizdoust, B.

doi:10.1107/S160053681200390X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m246-m247

doi:10.1107/S160053681200390X

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Dichlorido{1-[N-(5-chloro-2-oxidophenyl)carboximidoyl]naphthalen-2-olato-κ³O,N,O′}(methanol-κO)tin(IV)

Gholam Hossein Shahverdizadeh,^a ‡ Seik Weng Ng,^b,^c Edward R. T. Tiekink ^b ^* and Babak Mirtamizdoust ^d

^aDepartment of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, PO Box 1655, Tabriz, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^dDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Tabriz, PO Box 5166616471, Tabriz, Iran
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 28 January 2012; accepted 30 January 2012; online 4 February 2012)

In the title complex, [Sn(C₁₇H₁₀ClNO₂)Cl₂(CH₃OH)], the Sn^IV atom features a distorted octahedral geometry defined by the O,N,O′-donors of the dianion, two Cl atoms and the methanol O atom. The six-membered chelate ring has a half-chair conformation with the Sn atom lying 0.449 (4) Å out of the plane defined by the remaining atoms (r.m.s. deviation = 0.0238 Å). Supramolecular helical chains along [100], mediated by O—H⋯O hydrogen bonds, feature in the crystal packing. Chains are linked by C—H⋯O, C—H⋯Cl and π–π [centroid–centroid distance = 3.598 (2) Å] interactions.

Related literature

For background to related Sn(IV) Schiff base compounds and a closely related structure, see: Pettinari et al. (2001 ). For specialized crystallization techniques, see: Harrowfield et al. (1996 ).

Experimental

Crystal data

[Sn(C₁₇H₁₀ClNO₂)Cl₂(CH₄O)]
M_r = 517.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.9767 (3) Å
b = 11.1639 (3) Å
c = 16.2755 (5) Å
V = 1812.75 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.87 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.819, T_max = 1.000
6571 measured reflections
4139 independent reflections
3913 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.059
S = 1.01
4139 reflections
239 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.73 e Å⁻³
Absolute structure: Flack (1983 ), 1765 Friedel pairs
Flack parameter: −0.036 (19)

Table 1
Selected bond lengths (Å)

Sn—Cl1	2.3398 (10)
Sn—Cl2	2.3807 (9)
Sn—O1	2.050 (2)
Sn—O2	2.010 (3)
Sn—O3	2.174 (3)
Sn—N1	2.144 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O1ⁱ	0.84 (1)	1.80 (1)	2.633 (4)	174 (4)
C2—H2⋯O2ⁱⁱ	0.95	2.50	3.363 (4)	151
C16—H16⋯Cl3ⁱⁱⁱ	0.95	2.74	3.542 (4)	143
C18—H18A⋯Cl2ⁱ	0.98	2.77	3.707 (4)	161
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681200390X/hg5171sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200390X/hg5171Isup2.hkl

checkCIF report

Comment top

Original interest in tin(IV) compounds with Schiff bases ligands based on the 2-{[(2-hydroxyphenyl)imino]methyl}phenol parent compound stemmed from possible applications in medicinal chemistry (Pettinari et al., 2001). This motivated the synthesis and characterization of the title compound, (I).

In (I), Fig. 1, the Sn^IV atom is coordinated by the tridentate, dinegative Schiff base, two Cl atoms and the O atom of a methanol molecule to define a distorted octahedral geometry within a Cl₂NO₃ donor set, Table 1. The five-membered chelate ring is approximately planar with a r.m.s. deviation of 0.058 Å. By contrast, the six-membered chelate ring has a half-chair conformation as the Sn atom lies 0.449 (4) Å out of the plane defined by the five remaining atoms (r.m.s. deviation = 0.024 Å). The Sn—Cl2 bond length is significantly longer than that of Sn—Cl1, a difference which is correlated with the Cl2 atom being trans to the methanol-O atom.

The most significant feature of the crystal packing is the formation of helical supramolecular chains along [100] mediated by O—H···O hydrogen bonding, Fig. 2 and Table 2. Chains are consolidated in the crystal packing by C—H···O and C—H···Cl interactions. Further stability is provided by π–π contacts [ring centroid(C1–C6)···ring centroid(C8,C9,C14–C17)ⁱ = 3.598 (2) Å, angle = 10.47 (17)° for i: 1 - x, 1/2 + y, 3/2 - z).

Related literature top

For background to related Sn(IV) Schiff base compounds and a closely related structure, see: Pettinari et al. (2001). For specialized crystallization techniques, see: Harrowfield et al. (1996).

Experimental top

A solution of 2-amino-4-chlorophenol (10 mmol) in EtOH (30 ml) was added drop-wise to the solution of 2-hydroxy-1-naphthaldehyde (10 mmol) in EtOH (20 ml). The mixture was refluxed for 5 h. The yellow precipitate was removed by filtration and recrystallized from MeOH solution. The ligand (0.5 mmol) was placed in one arm of a branched tube (Harrowfield et al., 1996) and tin(IV) chloride (0.5 mmol) in the other. Methanol was then added to fill both arms, the tube sealed and the ligand-containing arm immersed in a bath at 333 K, while the other was left at ambient temperature. After three weeks crystals deposited in the arm held at ambient temperature. They were filtered off, washed with acetone and ether, and air-dried. Yield: 68%. M.pt.: 571 K (dec.).

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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
	Fig. 2. View of the supramolecular chain along [100] in (I) mediated by O—H···O hydrogen bonding shown as orange dashed lines.
	Fig. 3. A view in projection down the a axis of the unit-cell contents of (I). The C—H···O, C—H···Cl and π–π interactions are shown as orange, blue and purple dashed lines.

Dichlorido{1-[N-(5-chloro-2-oxidophenyl)carboximidoyl]naphthalen-2- olato-κ³O,N,O'}(methanol-κO)tin(IV) top

Crystal data top

[Sn(C₁₇H₁₀ClNO₂)Cl₂(CH₄O)]	F(000) = 1016
M_r = 517.34	D_x = 1.896 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4166 reflections
a = 9.9767 (3) Å	θ = 2.2–27.5°
b = 11.1639 (3) Å	µ = 1.87 mm⁻¹
c = 16.2755 (5) Å	T = 100 K
V = 1812.75 (9) Å³	Prism, brown
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4139 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3913 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.024
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ω scan	h = −12→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→14
T_min = 0.819, T_max = 1.000	l = −21→20
6571 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.0231P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
4139 reflections	Δρ_max = 0.54 e Å⁻³
239 parameters	Δρ_min = −0.73 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1765 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.036 (19)

Crystal data top

[Sn(C₁₇H₁₀ClNO₂)Cl₂(CH₄O)]	V = 1812.75 (9) Å³
M_r = 517.34	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.9767 (3) Å	µ = 1.87 mm⁻¹
b = 11.1639 (3) Å	T = 100 K
c = 16.2755 (5) Å	0.25 × 0.20 × 0.15 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4139 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3913 reflections with I > 2σ(I)
T_min = 0.819, T_max = 1.000	R_int = 0.024
6571 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.059	Δρ_max = 0.54 e Å⁻³
S = 1.01	Δρ_min = −0.73 e Å⁻³
4139 reflections	Absolute structure: Flack (1983), 1765 Friedel pairs
239 parameters	Absolute structure parameter: −0.036 (19)
1 restraint

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(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

	x	y	z	U_iso*/U_eq
Sn	0.39500 (3)	0.17557 (2)	0.915201 (14)	0.01147 (6)
Cl1	0.27998 (11)	0.03339 (8)	0.99384 (6)	0.0222 (2)
Cl2	0.27645 (10)	0.15018 (8)	0.78945 (5)	0.0197 (2)
Cl3	0.50466 (11)	0.79039 (7)	0.89690 (6)	0.0188 (2)
O1	0.2770 (2)	0.3133 (2)	0.95636 (14)	0.0121 (5)
O2	0.5532 (3)	0.0747 (2)	0.88264 (15)	0.0146 (6)
O3	0.5167 (3)	0.2113 (2)	1.02329 (15)	0.0149 (6)
H3O	0.5989 (13)	0.198 (3)	1.029 (2)	0.021 (11)*
N1	0.5035 (3)	0.3262 (3)	0.86761 (16)	0.0119 (6)
C1	0.3288 (4)	0.4240 (3)	0.9413 (2)	0.0113 (8)
C2	0.2641 (4)	0.5253 (3)	0.9715 (2)	0.0112 (7)
H2	0.1836	0.5175	1.0023	0.013*
C3	0.3185 (4)	0.6384 (3)	0.9563 (2)	0.0137 (8)
H3	0.2741	0.7083	0.9756	0.016*
C4	0.4377 (4)	0.6482 (3)	0.9128 (2)	0.0136 (7)
C5	0.5029 (4)	0.5491 (3)	0.8821 (2)	0.0124 (8)
H5	0.5840	0.5580	0.8521	0.015*
C6	0.4490 (4)	0.4361 (3)	0.8953 (2)	0.0123 (8)
C7	0.6067 (4)	0.3186 (3)	0.81737 (18)	0.0125 (7)
H7	0.6401	0.3918	0.7958	0.015*
C8	0.6736 (4)	0.2118 (3)	0.7921 (2)	0.0110 (7)
C9	0.7848 (4)	0.2219 (3)	0.7340 (2)	0.0133 (8)
C10	0.8181 (4)	0.3302 (4)	0.6923 (2)	0.0144 (7)
H10	0.7644	0.3995	0.7006	0.017*
C11	0.9261 (4)	0.3361 (3)	0.6407 (2)	0.0189 (8)
H11	0.9456	0.4093	0.6135	0.023*
C12	1.0089 (4)	0.2361 (3)	0.6272 (2)	0.0196 (9)
H12	1.0856	0.2423	0.5929	0.023*
C13	0.9775 (4)	0.1303 (3)	0.6639 (2)	0.0166 (8)
H13	1.0317	0.0619	0.6538	0.020*
C14	0.8661 (4)	0.1203 (3)	0.7168 (2)	0.0138 (8)
C15	0.8323 (4)	0.0086 (3)	0.7535 (2)	0.0172 (8)
H15	0.8852	−0.0599	0.7413	0.021*
C16	0.7278 (4)	−0.0026 (3)	0.8048 (2)	0.0175 (9)
H16	0.7070	−0.0790	0.8271	0.021*
C17	0.6474 (4)	0.0978 (3)	0.8264 (2)	0.0115 (8)
C18	0.4697 (4)	0.2485 (4)	1.1025 (2)	0.0243 (10)
H18A	0.5462	0.2583	1.1397	0.036*
H18B	0.4087	0.1877	1.1247	0.036*
H18C	0.4220	0.3249	1.0974	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.00915 (11)	0.01150 (10)	0.01375 (11)	−0.00087 (11)	0.00154 (11)	−0.00057 (11)
Cl1	0.0196 (5)	0.0204 (4)	0.0265 (5)	−0.0049 (4)	0.0050 (5)	0.0019 (4)
Cl2	0.0179 (5)	0.0225 (5)	0.0187 (4)	−0.0008 (4)	−0.0027 (4)	−0.0060 (4)
Cl3	0.0204 (5)	0.0125 (4)	0.0237 (5)	−0.0033 (4)	0.0017 (4)	−0.0002 (3)
O1	0.0082 (13)	0.0103 (11)	0.0176 (12)	−0.0012 (11)	0.0042 (10)	−0.0011 (11)
O2	0.0136 (15)	0.0138 (12)	0.0166 (12)	0.0019 (10)	0.0064 (11)	0.0044 (11)
O3	0.0062 (14)	0.0246 (14)	0.0138 (12)	0.0026 (12)	0.0009 (12)	−0.0019 (11)
N1	0.0089 (15)	0.0126 (13)	0.0141 (13)	−0.0011 (15)	−0.0002 (12)	−0.0006 (14)
C1	0.012 (2)	0.0145 (16)	0.0078 (15)	−0.0021 (15)	−0.0013 (15)	0.0028 (14)
C2	0.0077 (19)	0.0168 (16)	0.0091 (16)	0.0018 (15)	−0.0013 (15)	−0.0028 (15)
C3	0.012 (2)	0.0154 (17)	0.0135 (17)	0.0014 (15)	−0.0021 (16)	−0.0020 (15)
C4	0.0153 (19)	0.0120 (16)	0.0137 (15)	−0.0025 (13)	−0.0055 (16)	0.0029 (16)
C5	0.010 (2)	0.0152 (17)	0.0124 (16)	−0.0014 (15)	−0.0013 (16)	0.0041 (15)
C6	0.0124 (19)	0.0162 (16)	0.0082 (17)	0.0005 (14)	−0.0024 (14)	−0.0002 (14)
C7	0.0123 (17)	0.0130 (14)	0.0122 (15)	−0.0007 (19)	−0.0006 (15)	0.0019 (15)
C8	0.0089 (19)	0.0152 (17)	0.0088 (16)	0.0019 (14)	−0.0014 (14)	0.0000 (14)
C9	0.011 (2)	0.0194 (17)	0.0096 (16)	−0.0009 (16)	−0.0011 (16)	−0.0028 (15)
C10	0.0099 (18)	0.0185 (17)	0.0148 (16)	0.0017 (17)	−0.0004 (14)	−0.0010 (17)
C11	0.019 (2)	0.0210 (18)	0.0165 (16)	−0.0055 (18)	0.0011 (15)	0.0042 (17)
C12	0.009 (2)	0.033 (2)	0.0164 (19)	−0.0003 (18)	0.0017 (17)	0.0039 (18)
C13	0.009 (2)	0.0265 (19)	0.0142 (17)	0.0038 (16)	0.0000 (16)	0.0002 (17)
C14	0.009 (2)	0.0210 (18)	0.0110 (16)	−0.0010 (15)	0.0012 (15)	−0.0001 (15)
C15	0.020 (2)	0.0184 (19)	0.0131 (18)	0.0062 (16)	−0.0024 (17)	−0.0034 (16)
C16	0.021 (2)	0.0137 (17)	0.0176 (18)	0.0028 (17)	0.0003 (17)	0.0024 (16)
C17	0.0099 (19)	0.0155 (16)	0.0089 (16)	0.0004 (15)	−0.0001 (14)	−0.0021 (15)
C18	0.016 (2)	0.043 (2)	0.0141 (19)	0.0063 (19)	0.0019 (17)	−0.0063 (18)

Geometric parameters (Å, º) top

Sn—Cl1	2.3398 (10)	C7—C8	1.427 (5)
Sn—Cl2	2.3807 (9)	C7—H7	0.9500
Sn—O1	2.050 (2)	C8—C17	1.414 (5)
Sn—O2	2.010 (3)	C8—C9	1.462 (5)
Sn—O3	2.174 (3)	C9—C14	1.422 (5)
Sn—N1	2.144 (3)	C9—C10	1.426 (5)
Cl3—C4	1.742 (3)	C10—C11	1.368 (5)
O1—C1	1.361 (4)	C10—H10	0.9500
O2—C17	1.337 (4)	C11—C12	1.406 (5)
O3—C18	1.434 (4)	C11—H11	0.9500
O3—H3O	0.840 (10)	C12—C13	1.360 (5)
N1—C7	1.318 (4)	C12—H12	0.9500
N1—C6	1.416 (5)	C13—C14	1.410 (5)
C1—C2	1.392 (5)	C13—H13	0.9500
C1—C6	1.420 (5)	C14—C15	1.423 (5)
C2—C3	1.397 (5)	C15—C16	1.342 (5)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.388 (5)	C16—C17	1.422 (5)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.377 (5)	C18—H18A	0.9800
C5—C6	1.388 (5)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800

O2—Sn—O1	163.28 (10)	N1—C6—C1	114.2 (3)
O2—Sn—N1	87.01 (11)	N1—C7—C8	126.7 (3)
O1—Sn—N1	79.61 (11)	N1—C7—H7	116.6
O2—Sn—O3	82.99 (10)	C8—C7—H7	116.6
O1—Sn—O3	85.31 (10)	C17—C8—C7	123.5 (3)
N1—Sn—O3	82.33 (10)	C17—C8—C9	117.7 (3)
O2—Sn—Cl1	98.58 (7)	C7—C8—C9	118.5 (3)
O1—Sn—Cl1	92.78 (7)	C14—C9—C10	116.7 (3)
N1—Sn—Cl1	167.70 (8)	C14—C9—C8	119.9 (3)
O3—Sn—Cl1	87.47 (7)	C10—C9—C8	123.3 (3)
O2—Sn—Cl2	95.55 (8)	C11—C10—C9	121.0 (4)
O1—Sn—Cl2	94.87 (7)	C11—C10—H10	119.5
N1—Sn—Cl2	91.92 (8)	C9—C10—H10	119.5
O3—Sn—Cl2	174.12 (7)	C10—C11—C12	121.4 (4)
Cl1—Sn—Cl2	98.39 (4)	C10—C11—H11	119.3
C1—O1—Sn	113.8 (2)	C12—C11—H11	119.3
C17—O2—Sn	128.6 (2)	C13—C12—C11	119.0 (4)
C18—O3—Sn	126.8 (2)	C13—C12—H12	120.5
C18—O3—H3O	106 (3)	C11—C12—H12	120.5
Sn—O3—H3O	127 (3)	C12—C13—C14	121.2 (4)
C7—N1—C6	123.6 (3)	C12—C13—H13	119.4
C7—N1—Sn	124.6 (3)	C14—C13—H13	119.4
C6—N1—Sn	111.8 (2)	C13—C14—C9	120.4 (3)
O1—C1—C2	119.8 (3)	C13—C14—C15	120.8 (3)
O1—C1—C6	120.1 (3)	C9—C14—C15	118.7 (3)
C2—C1—C6	120.1 (3)	C16—C15—C14	121.8 (4)
C1—C2—C3	119.4 (3)	C16—C15—H15	119.1
C1—C2—H2	120.3	C14—C15—H15	119.1
C3—C2—H2	120.3	C15—C16—C17	121.2 (3)
C4—C3—C2	119.6 (3)	C15—C16—H16	119.4
C4—C3—H3	120.2	C17—C16—H16	119.4
C2—C3—H3	120.2	O2—C17—C8	125.0 (3)
C5—C4—C3	121.8 (3)	O2—C17—C16	114.4 (3)
C5—C4—Cl3	119.8 (3)	C8—C17—C16	120.5 (3)
C3—C4—Cl3	118.4 (3)	O3—C18—H18A	109.5
C4—C5—C6	119.4 (4)	O3—C18—H18B	109.5
C4—C5—H5	120.3	H18A—C18—H18B	109.5
C6—C5—H5	120.3	O3—C18—H18C	109.5
C5—C6—N1	126.2 (3)	H18A—C18—H18C	109.5
C5—C6—C1	119.7 (3)	H18B—C18—H18C	109.5

O2—Sn—O1—C1	31.6 (5)	Sn—N1—C6—C5	173.6 (3)
N1—Sn—O1—C1	−5.7 (2)	C7—N1—C6—C1	173.1 (3)
O3—Sn—O1—C1	77.3 (2)	Sn—N1—C6—C1	−5.7 (4)
Cl1—Sn—O1—C1	164.5 (2)	O1—C1—C6—C5	−178.4 (3)
Cl2—Sn—O1—C1	−96.8 (2)	C2—C1—C6—C5	1.3 (5)
O1—Sn—O2—C17	−59.1 (5)	O1—C1—C6—N1	1.0 (5)
N1—Sn—O2—C17	−22.5 (3)	C2—C1—C6—N1	−179.4 (3)
O3—Sn—O2—C17	−105.1 (3)	C6—N1—C7—C8	174.6 (3)
Cl1—Sn—O2—C17	168.6 (3)	Sn—N1—C7—C8	−6.8 (5)
Cl2—Sn—O2—C17	69.2 (3)	N1—C7—C8—C17	−8.3 (6)
O2—Sn—O3—C18	−156.5 (3)	N1—C7—C8—C9	178.5 (3)
O1—Sn—O3—C18	35.5 (3)	C17—C8—C9—C14	−2.9 (5)
N1—Sn—O3—C18	115.6 (3)	C7—C8—C9—C14	170.7 (3)
Cl1—Sn—O3—C18	−57.5 (3)	C17—C8—C9—C10	177.2 (3)
Cl2—Sn—O3—C18	127.5 (7)	C7—C8—C9—C10	−9.1 (5)
O2—Sn—N1—C7	17.5 (3)	C14—C9—C10—C11	−2.2 (5)
O1—Sn—N1—C7	−172.6 (3)	C8—C9—C10—C11	177.7 (3)
O3—Sn—N1—C7	100.8 (3)	C9—C10—C11—C12	−0.5 (5)
Cl1—Sn—N1—C7	135.0 (3)	C10—C11—C12—C13	2.5 (6)
Cl2—Sn—N1—C7	−78.0 (3)	C11—C12—C13—C14	−1.7 (6)
O2—Sn—N1—C6	−163.7 (2)	C12—C13—C14—C9	−1.0 (6)
O1—Sn—N1—C6	6.2 (2)	C12—C13—C14—C15	178.5 (4)
O3—Sn—N1—C6	−80.4 (2)	C10—C9—C14—C13	2.9 (5)
Cl1—Sn—N1—C6	−46.2 (5)	C8—C9—C14—C13	−176.9 (3)
Cl2—Sn—N1—C6	100.8 (2)	C10—C9—C14—C15	−176.7 (3)
Sn—O1—C1—C2	−175.1 (3)	C8—C9—C14—C15	3.5 (5)
Sn—O1—C1—C6	4.6 (4)	C13—C14—C15—C16	179.1 (4)
O1—C1—C2—C3	179.6 (3)	C9—C14—C15—C16	−1.3 (6)
C6—C1—C2—C3	−0.1 (5)	C14—C15—C16—C17	−1.5 (6)
C1—C2—C3—C4	−1.4 (5)	Sn—O2—C17—C8	16.4 (5)
C2—C3—C4—C5	1.7 (5)	Sn—O2—C17—C16	−166.4 (2)
C2—C3—C4—Cl3	−178.6 (3)	C7—C8—C17—O2	3.9 (6)
C3—C4—C5—C6	−0.5 (5)	C9—C8—C17—O2	177.3 (3)
Cl3—C4—C5—C6	179.8 (3)	C7—C8—C17—C16	−173.1 (3)
C4—C5—C6—N1	179.8 (3)	C9—C8—C17—C16	0.2 (5)
C4—C5—C6—C1	−1.0 (5)	C15—C16—C17—O2	−175.3 (3)
C7—N1—C6—C5	−7.6 (5)	C15—C16—C17—C8	2.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O1ⁱ	0.84 (1)	1.80 (1)	2.633 (4)	174 (4)
C2—H2···O2ⁱⁱ	0.95	2.50	3.363 (4)	151
C16—H16···Cl3ⁱⁱⁱ	0.95	2.74	3.542 (4)	143
C18—H18A···Cl2ⁱ	0.98	2.77	3.707 (4)	161

Symmetry codes: (i) x+1/2, −y+1/2, −z+2; (ii) x−1/2, −y+1/2, −z+2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Sn(C₁₇H₁₀ClNO₂)Cl₂(CH₄O)]
M_r	517.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	9.9767 (3), 11.1639 (3), 16.2755 (5)
V (Å³)	1812.75 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.87
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.819, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6571, 4139, 3913
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.059, 1.01
No. of reflections	4139
No. of parameters	239
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.73
Absolute structure	Flack (1983), 1765 Friedel pairs
Absolute structure parameter	−0.036 (19)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn—Cl1	2.3398 (10)	Sn—O2	2.010 (3)
Sn—Cl2	2.3807 (9)	Sn—O3	2.174 (3)
Sn—O1	2.050 (2)	Sn—N1	2.144 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O1ⁱ	0.840 (10)	1.796 (12)	2.633 (4)	174 (4)
C2—H2···O2ⁱⁱ	0.95	2.50	3.363 (4)	151
C16—H16···Cl3ⁱⁱⁱ	0.95	2.74	3.542 (4)	143
C18—H18A···Cl2ⁱ	0.98	2.77	3.707 (4)	161

Symmetry codes: (i) x+1/2, −y+1/2, −z+2; (ii) x−1/2, −y+1/2, −z+2; (iii) x, y−1, z.

Footnotes

‡Additional correspondence author, e-mail: shahverdizadeh@iaut.ac.ir.

Acknowledgements

We gratefully acknowledge support of this study by Tabriz Azad University, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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