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In the title compound, [SnCl2(C19H22N2O)]·CHCl3, the deprotonated N-(2-amino­cyclo­hexyl)­salicyl­ald­imine Schiff base chelates in an O,N,N′-tridentate manner to the Sn atom. The octahedral tin coordination environment is completed by a phenyl ring and two chloride ions; the bonded C atom of the phenyl ring along with the three chelating atoms comprise an approximate square plane. The mol­ecules of the complex are linked by N—H...O and N—H...Cl hydrogen bonds to form a helical chain running along the b axis; the solvent mol­ecules occupy the space between the chains but are not hydrogen bonded to them.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025036/hb6204sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025036/hb6204Isup2.hkl
Contains datablock I

CCDC reference: 255419

Key indicators

  • Single-crystal X-ray study
  • T = 223 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.041
  • wR factor = 0.114
  • Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT241_ALERT_2_A Check High U(eq) as Compared to Neighbors for C17
Author Response: This atom probably shows unresolved disorder over adjacent sites.

Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.83 Ratio PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors for C15 PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors for C18
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.43 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.31 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C19
Author Response: This atom probably shows unresolved disorder over adjacent sites.
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N2
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        C20
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C16    -   C17    ...       1.39 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

1 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

[N-(2-Aminocyclohexyl)salicylaldiminato-κ3O,N,N']dichlorophenyltin(IV) chloroform solvate top
Crystal data top
[SnCl2(C19H22N2O)]·CHCl3F(000) = 1200
Mr = 603.34Dx = 1.640 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 967 reflections
a = 11.877 (1) Åθ = 2.4–28.3°
b = 11.559 (1) ŵ = 1.61 mm1
c = 18.766 (2) ÅT = 223 K
β = 108.449 (2)°Block, colorless
V = 2443.9 (4) Å30.40 × 0.36 × 0.24 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
5614 independent reflections
Radiation source: medium-focus sealed tube4850 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1515
Tmin = 0.545, Tmax = 0.678k = 1415
16789 measured reflectionsl = 2416
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0648P)2 + 3.2538P]
where P = (Fo2 + 2Fc2)/3
5614 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 1.31 e Å3
0 restraintsΔρmin = 0.72 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.34057 (2)0.46627 (2)0.28778 (1)0.0312 (1)
Cl10.52697 (9)0.55029 (9)0.37183 (5)0.0476 (2)
Cl20.14078 (8)0.38936 (8)0.21909 (5)0.0434 (2)
Cl30.6614 (4)0.8219 (3)0.2025 (2)0.193 (2)
Cl40.7778 (2)0.6333 (3)0.2861 (2)0.146 (1)
Cl50.7091 (3)0.8252 (3)0.3605 (2)0.171 (1)
O10.4111 (2)0.3030 (2)0.3018 (1)0.0407 (6)
N10.2982 (3)0.4312 (3)0.3910 (2)0.0396 (7)
N20.2503 (3)0.6286 (2)0.3063 (2)0.0384 (6)
C10.3811 (3)0.5165 (3)0.1895 (2)0.035 (1)
C20.2955 (4)0.5717 (3)0.1303 (2)0.043 (1)
C30.3232 (4)0.6056 (4)0.0668 (2)0.052 (1)
C40.4343 (5)0.5855 (4)0.0621 (2)0.058 (1)
C50.5195 (4)0.5310 (4)0.1198 (3)0.058 (1)
C60.4931 (4)0.4962 (4)0.1837 (2)0.046 (1)
C70.4664 (3)0.2514 (3)0.3673 (2)0.037 (1)
C80.5506 (4)0.1667 (3)0.3686 (3)0.051 (1)
C90.6063 (4)0.1060 (4)0.4341 (3)0.064 (1)
C100.5796 (4)0.1268 (4)0.4993 (3)0.058 (1)
C110.4970 (4)0.2094 (3)0.4992 (2)0.045 (1)
C120.4400 (3)0.2739 (3)0.4343 (2)0.036 (1)
C130.3532 (4)0.3575 (3)0.4405 (2)0.040 (1)
C140.2082 (6)0.5127 (4)0.4029 (3)0.069 (2)
C150.1846 (4)0.5052 (4)0.4760 (2)0.047 (1)
C160.0996 (6)0.6013 (5)0.4832 (4)0.089 (2)
C170.1178 (9)0.7110 (6)0.4582 (4)0.132 (4)
C180.1436 (5)0.7188 (4)0.3861 (3)0.062 (1)
C190.2289 (6)0.6259 (4)0.3777 (3)0.079 (2)
C200.6741 (5)0.7421 (6)0.2808 (3)0.083 (2)
H2n10.29660.69080.30480.046*
H2n20.18010.63670.26890.046*
H20.21930.58570.13350.051*
H30.26560.64240.02690.062*
H40.45270.60920.01910.070*
H50.59540.51720.11590.070*
H60.55110.45900.22310.056*
H80.56980.15060.32470.061*
H90.66330.04970.43400.076*
H100.61770.08480.54320.069*
H110.47810.22330.54340.054*
H130.33520.35760.48580.048*
H140.13270.48790.36560.083*
H15a0.25960.51190.51720.056*
H15b0.14980.42960.48010.056*
H16a0.01850.57720.45530.107*
H16b0.10460.60740.53620.107*
H17a0.18390.74700.49720.158*
H17b0.04680.75750.45370.158*
H18a0.17760.79500.38260.074*
H18b0.06910.71210.34460.074*
H190.30600.64910.41400.095*
H200.59650.70480.27450.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0356 (1)0.0313 (1)0.0264 (1)0.00193 (8)0.0096 (1)0.00093 (8)
Cl10.0408 (5)0.0611 (6)0.0373 (5)0.0073 (4)0.0072 (4)0.0089 (4)
Cl20.0403 (4)0.0433 (5)0.0431 (5)0.0039 (4)0.0081 (4)0.0050 (4)
Cl30.324 (5)0.148 (2)0.120 (2)0.064 (3)0.092 (3)0.017 (2)
Cl40.097 (1)0.188 (3)0.166 (2)0.012 (2)0.060 (2)0.029 (2)
Cl50.214 (3)0.196 (3)0.140 (2)0.128 (2)0.107 (2)0.107 (2)
O10.051 (2)0.040 (1)0.029 (1)0.013 (1)0.010 (1)0.001 (1)
N10.055 (2)0.033 (1)0.037 (2)0.008 (1)0.022 (2)0.006 (1)
N20.046 (2)0.032 (1)0.039 (2)0.004 (1)0.017 (1)0.006 (1)
C10.042 (2)0.032 (2)0.030 (2)0.001 (1)0.012 (2)0.002 (1)
C20.051 (2)0.042 (2)0.037 (2)0.006 (2)0.016 (2)0.003 (2)
C30.070 (3)0.052 (2)0.036 (2)0.009 (2)0.020 (2)0.009 (2)
C40.084 (3)0.058 (3)0.045 (2)0.008 (2)0.039 (2)0.003 (2)
C50.052 (3)0.078 (3)0.053 (3)0.004 (2)0.029 (2)0.008 (2)
C60.044 (2)0.058 (2)0.038 (2)0.000 (2)0.015 (2)0.003 (2)
C70.040 (2)0.029 (2)0.036 (2)0.001 (1)0.005 (1)0.002 (1)
C80.056 (2)0.044 (2)0.049 (2)0.013 (2)0.014 (2)0.002 (2)
C90.063 (3)0.051 (2)0.069 (3)0.025 (2)0.009 (2)0.007 (2)
C100.068 (3)0.044 (2)0.049 (2)0.010 (2)0.002 (2)0.012 (2)
C110.055 (2)0.036 (2)0.036 (2)0.002 (2)0.004 (2)0.004 (2)
C120.042 (2)0.028 (2)0.032 (2)0.003 (1)0.004 (1)0.000 (1)
C130.059 (2)0.032 (2)0.032 (2)0.001 (2)0.018 (2)0.002 (1)
C140.101 (4)0.054 (3)0.078 (4)0.032 (3)0.064 (3)0.025 (2)
C150.053 (2)0.051 (2)0.042 (2)0.006 (2)0.024 (2)0.007 (2)
C160.124 (5)0.068 (3)0.116 (5)0.019 (3)0.096 (4)0.008 (3)
C170.218 (9)0.105 (5)0.124 (6)0.097 (6)0.127 (7)0.047 (5)
C180.089 (3)0.043 (2)0.067 (3)0.028 (2)0.044 (3)0.010 (2)
C190.132 (5)0.059 (3)0.072 (3)0.050 (3)0.070 (3)0.027 (2)
C200.081 (4)0.098 (4)0.081 (4)0.031 (3)0.040 (3)0.022 (3)
Geometric parameters (Å, º) top
Sn1—Cl12.474 (1)C15—C161.536 (7)
Sn1—Cl22.479 (1)C16—C171.392 (9)
Sn1—O12.048 (2)C17—C181.482 (7)
Sn1—C12.129 (4)C18—C191.519 (6)
Sn1—N12.188 (3)N2—H2n10.91
Sn1—N22.243 (3)N2—H2n20.91
Cl3—C201.701 (7)C2—H20.94
Cl4—C201.741 (7)C3—H30.94
Cl5—C201.715 (6)C4—H40.94
O1—C71.337 (4)C5—H50.94
N1—C131.278 (5)C6—H60.94
N1—C141.494 (5)C8—H80.94
N2—C191.440 (5)C9—H90.94
C1—C61.388 (5)C10—H100.94
C1—C21.400 (5)C11—H110.94
C2—C31.390 (5)C13—H130.94
C3—C41.370 (7)C14—H140.99
C4—C51.379 (7)C15—H15a0.98
C5—C61.392 (6)C15—H15b0.98
C7—C81.394 (5)C16—H16a0.98
C7—C121.413 (5)C16—H16b0.98
C8—C91.388 (6)C17—H17a0.98
C9—C101.378 (7)C17—H17b0.98
C10—C111.368 (6)C18—H18a0.98
C11—C121.406 (5)C18—H18b0.98
C12—C131.444 (5)C19—H190.99
C14—C191.438 (7)C20—H200.99
C14—C151.487 (6)
Cl1—Sn1—Cl2171.21 (3)Cl5—C20—Cl4112.5 (4)
Cl1—Sn1—O191.9 (1)C19—N2—H2n1109.4
Cl1—Sn1—C192.5 (1)Sn1—N2—H2n1109.4
Cl1—Sn1—N185.3 (1)C19—N2—H2n2109.4
Cl1—Sn1—N287.0 (1)Sn1—N2—H2n2109.4
Cl2—Sn1—O191.2 (1)H2n1—N2—H2n2108.0
Cl2—Sn1—N186.8 (1)C3—C2—H2120.0
Cl2—Sn1—N287.4 (1)C1—C2—H2120.0
Cl2—Sn1—C195.1 (1)C4—C3—H3119.9
O1—Sn1—N185.1 (1)C2—C3—H3119.9
O1—Sn1—N2161.4 (1)C3—C4—H4119.7
O1—Sn1—C199.7 (1)C5—C4—H4119.7
N1—Sn1—N276.3 (1)C4—C5—H5120.0
N1—Sn1—C1174.8 (1)C6—C5—H5120.0
N2—Sn1—C199.0 (1)C1—C6—H6120.0
C7—O1—Sn1126.2 (2)C5—C6—H6120.0
C13—N1—C14122.5 (3)C9—C8—H8119.7
C13—N1—Sn1124.0 (3)C7—C8—H8119.7
C14—N1—Sn1113.0 (2)C10—C9—H9119.4
C19—N2—Sn1111.1 (2)C8—C9—H9119.4
C6—C1—C2119.3 (4)C10—C11—H11119.3
C6—C1—Sn1120.4 (3)C12—C11—H11119.3
C2—C1—Sn1120.3 (3)N1—C13—H13116.5
C3—C2—C1119.9 (4)C12—C13—H13116.5
C4—C3—C2120.1 (4)C19—C14—H14104.0
C3—C4—C5120.6 (4)C15—C14—H14104.0
C4—C5—C6120.0 (4)N1—C14—H14104.0
C1—C6—C5120.1 (4)C14—C15—H15a109.4
O1—C7—C8118.1 (3)C16—C15—H15a109.4
O1—C7—C12123.6 (3)C14—C15—H15b109.4
C8—C7—C12118.3 (3)C16—C15—H15b109.4
C9—C8—C7120.6 (4)H15a—C15—H15b108.0
C10—C9—C8121.3 (4)C17—C16—H16a108.1
C11—C10—C9119.1 (4)C15—C16—H16a108.1
C11—C10—H10120.5C17—C16—H16b108.1
C9—C10—H10120.5C15—C16—H16b108.1
C10—C11—C12121.3 (4)H16a—C16—H16b107.3
C11—C12—C7119.4 (3)C16—C17—H17a107.9
C11—C12—C13116.4 (3)C18—C17—H17a107.9
C7—C12—C13124.1 (3)C16—C17—H17b107.9
N1—C13—C12126.9 (3)C18—C17—H17b107.9
C19—C14—C15117.3 (5)H17a—C17—H17b107.2
C19—C14—N1108.6 (4)C17—C18—H18a109.0
C15—C14—N1117.0 (4)C19—C18—H18a109.0
C14—C15—C16111.1 (4)C17—C18—H18b109.0
C17—C16—C15116.9 (5)C19—C18—H18b109.0
C16—C17—C18117.5 (6)H18a—C18—H18b107.8
C17—C18—C19112.9 (4)C14—C19—H19103.8
C14—C19—N2115.2 (4)N2—C19—H19103.8
C14—C19—C18114.8 (5)C18—C19—H19103.8
N2—C19—C18113.6 (4)Cl3—C20—H20107.9
Cl3—C20—Cl5112.3 (4)Cl5—C20—H20107.9
Cl3—C20—Cl4108.0 (4)Cl4—C20—H20107.9
C1—Sn1—O1—C7143.5 (3)Sn1—O1—C7—C8152.9 (3)
N1—Sn1—O1—C734.5 (3)Sn1—O1—C7—C1230.5 (5)
N2—Sn1—O1—C735.5 (5)O1—C7—C8—C9176.6 (4)
Cl1—Sn1—O1—C750.6 (3)C12—C7—C8—C90.2 (6)
Cl2—Sn1—O1—C7121.1 (3)C7—C8—C9—C100.5 (7)
O1—Sn1—N1—C1323.9 (3)C8—C9—C10—C110.3 (7)
N2—Sn1—N1—C13156.4 (3)C9—C10—C11—C120.6 (6)
Cl1—Sn1—N1—C1368.4 (3)C10—C11—C12—C71.3 (5)
Cl2—Sn1—N1—C13115.4 (3)C10—C11—C12—C13179.1 (4)
O1—Sn1—N1—C14163.4 (4)O1—C7—C12—C11175.5 (3)
N2—Sn1—N1—C1416.3 (4)C8—C7—C12—C111.1 (5)
Cl1—Sn1—N1—C14104.3 (4)O1—C7—C12—C132.1 (5)
Cl2—Sn1—N1—C1471.8 (4)C8—C7—C12—C13178.7 (4)
O1—Sn1—N2—C198.1 (6)C14—N1—C13—C12178.9 (4)
C1—Sn1—N2—C19170.9 (4)Sn1—N1—C13—C129.0 (6)
N1—Sn1—N2—C197.0 (4)C11—C12—C13—N1173.9 (4)
Cl1—Sn1—N2—C1978.9 (4)C7—C12—C13—N18.4 (6)
Cl2—Sn1—N2—C1994.3 (4)C13—N1—C14—C19135.8 (5)
O1—Sn1—C1—C645.7 (3)Sn1—N1—C14—C1937.1 (6)
N2—Sn1—C1—C6134.0 (3)C13—N1—C14—C150.2 (8)
Cl1—Sn1—C1—C646.6 (3)Sn1—N1—C14—C15172.7 (4)
Cl2—Sn1—C1—C6137.8 (3)C19—C14—C15—C1642.9 (8)
O1—Sn1—C1—C2135.0 (3)N1—C14—C15—C16174.6 (5)
N2—Sn1—C1—C245.3 (3)C14—C15—C16—C1741.7 (9)
Cl1—Sn1—C1—C2132.7 (3)C15—C16—C17—C1843.2 (12)
Cl2—Sn1—C1—C242.9 (3)C16—C17—C18—C1941.8 (11)
C6—C1—C2—C30.2 (6)C15—C14—C19—N2179.5 (5)
Sn1—C1—C2—C3179.1 (3)N1—C14—C19—N245.1 (7)
C1—C2—C3—C40.2 (6)C15—C14—C19—C1844.7 (8)
C2—C3—C4—C50.5 (7)N1—C14—C19—C18179.9 (5)
C3—C4—C5—C60.3 (7)Sn1—N2—C19—C1431.2 (7)
C2—C1—C6—C50.3 (6)Sn1—N2—C19—C18166.5 (4)
Sn1—C1—C6—C5179.0 (3)C17—C18—C19—C1441.6 (9)
C4—C5—C6—C10.0 (7)C17—C18—C19—N2177.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2n1···Cl2i0.912.503.372 (3)162
N2—H2n2···O1i0.912.393.065 (4)131
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

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