[N-(2-Amino­cyclo­hexyl)­salicyl­aldiminato-κ³O,N,N′]­di­chloro­phenyl­tin(IV) chloro­form solvate

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.

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

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Computing details

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

Crystal data

[SnCl2(C19H22N2O)]·CHCl3	F(000) = 1200
Mr = 603.34	Dx = 1.640 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 967 reflections
a = 11.877 (1) Å	θ = 2.4–28.3°
b = 11.559 (1) Å	µ = 1.61 mm^−1
c = 18.766 (2) Å	T = 223 K
β = 108.449 (2)°	Block, colorless
V = 2443.9 (4) Å^3	0.40 × 0.36 × 0.24 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	5614 independent reflections
Radiation source: medium-focus sealed tube	4850 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.545, Tmax = 0.678	k = −14→15
16789 measured reflections	l = −24→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 3.2538P] where P = (Fo^2 + 2Fc^2)/3
5614 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 1.31 e Å^−3
0 restraints	Δρmin = −0.72 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.34057 (2)	0.46627 (2)	0.28778 (1)	0.0312 (1)
Cl1	0.52697 (9)	0.55029 (9)	0.37183 (5)	0.0476 (2)
Cl2	0.14078 (8)	0.38936 (8)	0.21909 (5)	0.0434 (2)
Cl3	0.6614 (4)	0.8219 (3)	0.2025 (2)	0.193 (2)
Cl4	0.7778 (2)	0.6333 (3)	0.2861 (2)	0.146 (1)
Cl5	0.7091 (3)	0.8252 (3)	0.3605 (2)	0.171 (1)
O1	0.4111 (2)	0.3030 (2)	0.3018 (1)	0.0407 (6)
N1	0.2982 (3)	0.4312 (3)	0.3910 (2)	0.0396 (7)
N2	0.2503 (3)	0.6286 (2)	0.3063 (2)	0.0384 (6)
C1	0.3811 (3)	0.5165 (3)	0.1895 (2)	0.035 (1)
C2	0.2955 (4)	0.5717 (3)	0.1303 (2)	0.043 (1)
C3	0.3232 (4)	0.6056 (4)	0.0668 (2)	0.052 (1)
C4	0.4343 (5)	0.5855 (4)	0.0621 (2)	0.058 (1)
C5	0.5195 (4)	0.5310 (4)	0.1198 (3)	0.058 (1)
C6	0.4931 (4)	0.4962 (4)	0.1837 (2)	0.046 (1)
C7	0.4664 (3)	0.2514 (3)	0.3673 (2)	0.037 (1)
C8	0.5506 (4)	0.1667 (3)	0.3686 (3)	0.051 (1)
C9	0.6063 (4)	0.1060 (4)	0.4341 (3)	0.064 (1)
C10	0.5796 (4)	0.1268 (4)	0.4993 (3)	0.058 (1)
C11	0.4970 (4)	0.2094 (3)	0.4992 (2)	0.045 (1)
C12	0.4400 (3)	0.2739 (3)	0.4343 (2)	0.036 (1)
C13	0.3532 (4)	0.3575 (3)	0.4405 (2)	0.040 (1)
C14	0.2082 (6)	0.5127 (4)	0.4029 (3)	0.069 (2)
C15	0.1846 (4)	0.5052 (4)	0.4760 (2)	0.047 (1)
C16	0.0996 (6)	0.6013 (5)	0.4832 (4)	0.089 (2)
C17	0.1178 (9)	0.7110 (6)	0.4582 (4)	0.132 (4)
C18	0.1436 (5)	0.7188 (4)	0.3861 (3)	0.062 (1)
C19	0.2289 (6)	0.6259 (4)	0.3777 (3)	0.079 (2)
C20	0.6741 (5)	0.7421 (6)	0.2808 (3)	0.083 (2)
H2n1	0.2966	0.6908	0.3048	0.046*
H2n2	0.1801	0.6367	0.2689	0.046*
H2	0.2193	0.5857	0.1335	0.051*
H3	0.2656	0.6424	0.0269	0.062*
H4	0.4527	0.6092	0.0191	0.070*
H5	0.5954	0.5172	0.1159	0.070*
H6	0.5511	0.4590	0.2231	0.056*
H8	0.5698	0.1506	0.3247	0.061*
H9	0.6633	0.0497	0.4340	0.076*
H10	0.6177	0.0848	0.5432	0.069*
H11	0.4781	0.2233	0.5434	0.054*
H13	0.3352	0.3576	0.4858	0.048*
H14	0.1327	0.4879	0.3656	0.083*
H15a	0.2596	0.5119	0.5172	0.056*
H15b	0.1498	0.4296	0.4801	0.056*
H16a	0.0185	0.5772	0.4553	0.107*
H16b	0.1046	0.6074	0.5362	0.107*
H17a	0.1839	0.7470	0.4972	0.158*
H17b	0.0468	0.7575	0.4537	0.158*
H18a	0.1776	0.7950	0.3826	0.074*
H18b	0.0691	0.7121	0.3446	0.074*
H19	0.3060	0.6491	0.4140	0.095*
H20	0.5965	0.7048	0.2745	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0356 (1)	0.0313 (1)	0.0264 (1)	0.00193 (8)	0.0096 (1)	0.00093 (8)
Cl1	0.0408 (5)	0.0611 (6)	0.0373 (5)	−0.0073 (4)	0.0072 (4)	−0.0089 (4)
Cl2	0.0403 (4)	0.0433 (5)	0.0431 (5)	−0.0039 (4)	0.0081 (4)	−0.0050 (4)
Cl3	0.324 (5)	0.148 (2)	0.120 (2)	−0.064 (3)	0.092 (3)	0.017 (2)
Cl4	0.097 (1)	0.188 (3)	0.166 (2)	−0.012 (2)	0.060 (2)	−0.029 (2)
Cl5	0.214 (3)	0.196 (3)	0.140 (2)	−0.128 (2)	0.107 (2)	−0.107 (2)
O1	0.051 (2)	0.040 (1)	0.029 (1)	0.013 (1)	0.010 (1)	−0.001 (1)
N1	0.055 (2)	0.033 (1)	0.037 (2)	0.008 (1)	0.022 (2)	0.006 (1)
N2	0.046 (2)	0.032 (1)	0.039 (2)	0.004 (1)	0.017 (1)	0.006 (1)
C1	0.042 (2)	0.032 (2)	0.030 (2)	−0.001 (1)	0.012 (2)	−0.002 (1)
C2	0.051 (2)	0.042 (2)	0.037 (2)	0.006 (2)	0.016 (2)	0.003 (2)
C3	0.070 (3)	0.052 (2)	0.036 (2)	0.009 (2)	0.020 (2)	0.009 (2)
C4	0.084 (3)	0.058 (3)	0.045 (2)	−0.008 (2)	0.039 (2)	0.003 (2)
C5	0.052 (3)	0.078 (3)	0.053 (3)	−0.004 (2)	0.029 (2)	−0.008 (2)
C6	0.044 (2)	0.058 (2)	0.038 (2)	0.000 (2)	0.015 (2)	−0.003 (2)
C7	0.040 (2)	0.029 (2)	0.036 (2)	−0.001 (1)	0.005 (1)	−0.002 (1)
C8	0.056 (2)	0.044 (2)	0.049 (2)	0.013 (2)	0.014 (2)	−0.002 (2)
C9	0.063 (3)	0.051 (2)	0.069 (3)	0.025 (2)	0.009 (2)	0.007 (2)
C10	0.068 (3)	0.044 (2)	0.049 (2)	0.010 (2)	0.002 (2)	0.012 (2)
C11	0.055 (2)	0.036 (2)	0.036 (2)	−0.002 (2)	0.004 (2)	0.004 (2)
C12	0.042 (2)	0.028 (2)	0.032 (2)	−0.003 (1)	0.004 (1)	0.000 (1)
C13	0.059 (2)	0.032 (2)	0.032 (2)	−0.001 (2)	0.018 (2)	0.002 (1)
C14	0.101 (4)	0.054 (3)	0.078 (4)	0.032 (3)	0.064 (3)	0.025 (2)
C15	0.053 (2)	0.051 (2)	0.042 (2)	0.006 (2)	0.024 (2)	0.007 (2)
C16	0.124 (5)	0.068 (3)	0.116 (5)	0.019 (3)	0.096 (4)	0.008 (3)
C17	0.218 (9)	0.105 (5)	0.124 (6)	0.097 (6)	0.127 (7)	0.047 (5)
C18	0.089 (3)	0.043 (2)	0.067 (3)	0.028 (2)	0.044 (3)	0.010 (2)
C19	0.132 (5)	0.059 (3)	0.072 (3)	0.050 (3)	0.070 (3)	0.027 (2)
C20	0.081 (4)	0.098 (4)	0.081 (4)	−0.031 (3)	0.040 (3)	−0.022 (3)

Geometric parameters (Å, º)

Sn1—Cl1	2.474 (1)	C15—C16	1.536 (7)
Sn1—Cl2	2.479 (1)	C16—C17	1.392 (9)
Sn1—O1	2.048 (2)	C17—C18	1.482 (7)
Sn1—C1	2.129 (4)	C18—C19	1.519 (6)
Sn1—N1	2.188 (3)	N2—H2n1	0.91
Sn1—N2	2.243 (3)	N2—H2n2	0.91
Cl3—C20	1.701 (7)	C2—H2	0.94
Cl4—C20	1.741 (7)	C3—H3	0.94
Cl5—C20	1.715 (6)	C4—H4	0.94
O1—C7	1.337 (4)	C5—H5	0.94
N1—C13	1.278 (5)	C6—H6	0.94
N1—C14	1.494 (5)	C8—H8	0.94
N2—C19	1.440 (5)	C9—H9	0.94
C1—C6	1.388 (5)	C10—H10	0.94
C1—C2	1.400 (5)	C11—H11	0.94
C2—C3	1.390 (5)	C13—H13	0.94
C3—C4	1.370 (7)	C14—H14	0.99
C4—C5	1.379 (7)	C15—H15a	0.98
C5—C6	1.392 (6)	C15—H15b	0.98
C7—C8	1.394 (5)	C16—H16a	0.98
C7—C12	1.413 (5)	C16—H16b	0.98
C8—C9	1.388 (6)	C17—H17a	0.98
C9—C10	1.378 (7)	C17—H17b	0.98
C10—C11	1.368 (6)	C18—H18a	0.98
C11—C12	1.406 (5)	C18—H18b	0.98
C12—C13	1.444 (5)	C19—H19	0.99
C14—C19	1.438 (7)	C20—H20	0.99
C14—C15	1.487 (6)
Cl1—Sn1—Cl2	171.21 (3)	Cl5—C20—Cl4	112.5 (4)
Cl1—Sn1—O1	91.9 (1)	C19—N2—H2n1	109.4
Cl1—Sn1—C1	92.5 (1)	Sn1—N2—H2n1	109.4
Cl1—Sn1—N1	85.3 (1)	C19—N2—H2n2	109.4
Cl1—Sn1—N2	87.0 (1)	Sn1—N2—H2n2	109.4
Cl2—Sn1—O1	91.2 (1)	H2n1—N2—H2n2	108.0
Cl2—Sn1—N1	86.8 (1)	C3—C2—H2	120.0
Cl2—Sn1—N2	87.4 (1)	C1—C2—H2	120.0
Cl2—Sn1—C1	95.1 (1)	C4—C3—H3	119.9
O1—Sn1—N1	85.1 (1)	C2—C3—H3	119.9
O1—Sn1—N2	161.4 (1)	C3—C4—H4	119.7
O1—Sn1—C1	99.7 (1)	C5—C4—H4	119.7
N1—Sn1—N2	76.3 (1)	C4—C5—H5	120.0
N1—Sn1—C1	174.8 (1)	C6—C5—H5	120.0
N2—Sn1—C1	99.0 (1)	C1—C6—H6	120.0
C7—O1—Sn1	126.2 (2)	C5—C6—H6	120.0
C13—N1—C14	122.5 (3)	C9—C8—H8	119.7
C13—N1—Sn1	124.0 (3)	C7—C8—H8	119.7
C14—N1—Sn1	113.0 (2)	C10—C9—H9	119.4
C19—N2—Sn1	111.1 (2)	C8—C9—H9	119.4
C6—C1—C2	119.3 (4)	C10—C11—H11	119.3
C6—C1—Sn1	120.4 (3)	C12—C11—H11	119.3
C2—C1—Sn1	120.3 (3)	N1—C13—H13	116.5
C3—C2—C1	119.9 (4)	C12—C13—H13	116.5
C4—C3—C2	120.1 (4)	C19—C14—H14	104.0
C3—C4—C5	120.6 (4)	C15—C14—H14	104.0
C4—C5—C6	120.0 (4)	N1—C14—H14	104.0
C1—C6—C5	120.1 (4)	C14—C15—H15a	109.4
O1—C7—C8	118.1 (3)	C16—C15—H15a	109.4
O1—C7—C12	123.6 (3)	C14—C15—H15b	109.4
C8—C7—C12	118.3 (3)	C16—C15—H15b	109.4
C9—C8—C7	120.6 (4)	H15a—C15—H15b	108.0
C10—C9—C8	121.3 (4)	C17—C16—H16a	108.1
C11—C10—C9	119.1 (4)	C15—C16—H16a	108.1
C11—C10—H10	120.5	C17—C16—H16b	108.1
C9—C10—H10	120.5	C15—C16—H16b	108.1
C10—C11—C12	121.3 (4)	H16a—C16—H16b	107.3
C11—C12—C7	119.4 (3)	C16—C17—H17a	107.9
C11—C12—C13	116.4 (3)	C18—C17—H17a	107.9
C7—C12—C13	124.1 (3)	C16—C17—H17b	107.9
N1—C13—C12	126.9 (3)	C18—C17—H17b	107.9
C19—C14—C15	117.3 (5)	H17a—C17—H17b	107.2
C19—C14—N1	108.6 (4)	C17—C18—H18a	109.0
C15—C14—N1	117.0 (4)	C19—C18—H18a	109.0
C14—C15—C16	111.1 (4)	C17—C18—H18b	109.0
C17—C16—C15	116.9 (5)	C19—C18—H18b	109.0
C16—C17—C18	117.5 (6)	H18a—C18—H18b	107.8
C17—C18—C19	112.9 (4)	C14—C19—H19	103.8
C14—C19—N2	115.2 (4)	N2—C19—H19	103.8
C14—C19—C18	114.8 (5)	C18—C19—H19	103.8
N2—C19—C18	113.6 (4)	Cl3—C20—H20	107.9
Cl3—C20—Cl5	112.3 (4)	Cl5—C20—H20	107.9
Cl3—C20—Cl4	108.0 (4)	Cl4—C20—H20	107.9
C1—Sn1—O1—C7	143.5 (3)	Sn1—O1—C7—C8	−152.9 (3)
N1—Sn1—O1—C7	−34.5 (3)	Sn1—O1—C7—C12	30.5 (5)
N2—Sn1—O1—C7	−35.5 (5)	O1—C7—C8—C9	−176.6 (4)
Cl1—Sn1—O1—C7	50.6 (3)	C12—C7—C8—C9	0.2 (6)
Cl2—Sn1—O1—C7	−121.1 (3)	C7—C8—C9—C10	0.5 (7)
O1—Sn1—N1—C13	23.9 (3)	C8—C9—C10—C11	−0.3 (7)
N2—Sn1—N1—C13	−156.4 (3)	C9—C10—C11—C12	−0.6 (6)
Cl1—Sn1—N1—C13	−68.4 (3)	C10—C11—C12—C7	1.3 (5)
Cl2—Sn1—N1—C13	115.4 (3)	C10—C11—C12—C13	179.1 (4)
O1—Sn1—N1—C14	−163.4 (4)	O1—C7—C12—C11	175.5 (3)
N2—Sn1—N1—C14	16.3 (4)	C8—C7—C12—C11	−1.1 (5)
Cl1—Sn1—N1—C14	104.3 (4)	O1—C7—C12—C13	−2.1 (5)
Cl2—Sn1—N1—C14	−71.8 (4)	C8—C7—C12—C13	−178.7 (4)
O1—Sn1—N2—C19	8.1 (6)	C14—N1—C13—C12	178.9 (4)
C1—Sn1—N2—C19	−170.9 (4)	Sn1—N1—C13—C12	−9.0 (6)
N1—Sn1—N2—C19	7.0 (4)	C11—C12—C13—N1	173.9 (4)
Cl1—Sn1—N2—C19	−78.9 (4)	C7—C12—C13—N1	−8.4 (6)
Cl2—Sn1—N2—C19	94.3 (4)	C13—N1—C14—C19	135.8 (5)
O1—Sn1—C1—C6	−45.7 (3)	Sn1—N1—C14—C19	−37.1 (6)
N2—Sn1—C1—C6	134.0 (3)	C13—N1—C14—C15	0.2 (8)
Cl1—Sn1—C1—C6	46.6 (3)	Sn1—N1—C14—C15	−172.7 (4)
Cl2—Sn1—C1—C6	−137.8 (3)	C19—C14—C15—C16	42.9 (8)
O1—Sn1—C1—C2	135.0 (3)	N1—C14—C15—C16	174.6 (5)
N2—Sn1—C1—C2	−45.3 (3)	C14—C15—C16—C17	−41.7 (9)
Cl1—Sn1—C1—C2	−132.7 (3)	C15—C16—C17—C18	43.2 (12)
Cl2—Sn1—C1—C2	42.9 (3)	C16—C17—C18—C19	−41.8 (11)
C6—C1—C2—C3	−0.2 (6)	C15—C14—C19—N2	−179.5 (5)
Sn1—C1—C2—C3	179.1 (3)	N1—C14—C19—N2	45.1 (7)
C1—C2—C3—C4	−0.2 (6)	C15—C14—C19—C18	−44.7 (8)
C2—C3—C4—C5	0.5 (7)	N1—C14—C19—C18	179.9 (5)
C3—C4—C5—C6	−0.3 (7)	Sn1—N2—C19—C14	−31.2 (7)
C2—C1—C6—C5	0.3 (6)	Sn1—N2—C19—C18	−166.5 (4)
Sn1—C1—C6—C5	−179.0 (3)	C17—C18—C19—C14	41.6 (9)
C4—C5—C6—C1	0.0 (7)	C17—C18—C19—N2	177.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n1···Cl2^i	0.91	2.50	3.372 (3)	162
N2—H2n2···O1^i	0.91	2.39	3.065 (4)	131

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.