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The title compound, (C8H15N3)[SnCl6]·H2O, is a salt involving a doubly protonated amine cation and a divalent [SnCl6]2- anion. The solid-state structure agrees with that found by 1H NMR and 13C NMR analyses. The salt has potential for use in the synthesis of organometallic compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029454/fl6183sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029454/fl6183Isup2.hkl
Contains datablock I

CCDC reference: 287555

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.034
  • wR factor = 0.071
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.00 Ratio PLAT417_ALERT_2_B Short Inter D-H..H-D H1C .. H10 .. 1.85 Ang. PLAT731_ALERT_1_B Bond Calc 1.04(8), Rep 1.046(10) ...... 8.00 su-Rat O1 -H9 1.555 1.555
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1 PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1 - H9 ... 1.04 Ang. PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1 - H10 ... 1.04 Ang. PLAT731_ALERT_1_C Bond Calc 1.04(3), Rep 1.041(10) ...... 3.00 su-Rat O1 -H10 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.862(10) ...... 4.00 su-Rat N2 -H2 1.555 1.555
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title salt, (I), has found use in fields as varied as medical and organic intermediates. Furthermore, many metal complexes of ethylenediamine and its derivatives are biologically active. They can resist cancers and viruses, and can inhibit bacterial growth. Thus, in order to learn more about these compounds, we have synthesized compound (I), and report its structure here.

Compound (I) (Fig. 1) has been characterized by 1HNMR, 13CNMR analyses and contains a divalent amine cation and an [SnCl6]−2 anion. The amine cation is essentially planar (±0.028 Å), with the water molecule and the [SnCl6]−2 anion located at opposite ends of the plane. There are two hydrogen bonds, one between N1 and the water molecule [N1—H1c = 0.89 Å, H1c···O1 = 1.85 Å, N1···O1 = 2.736(?)Å and N1—H1c···O1 = 171] and a second between N3 and a Cl atom of the anion [N3—H3B = 0.89 Å, H3B···Cl4 = 2.64 Å, N3···Cl4 = 3.397(?)Å and N3—H3B···Cl4 = 143]. The [SnCl6]−2 anion has a distorted octahedral coordination, with the nearest Sn···N distance being Sn···N3 of 4.317 Å.

Experimental top

The title salt was synthesized according to Allali et al. (2004). 2-Nitrochlorobenzene and excess ethylenediamine were stirred 1 h under reflux. After the excess of ethylenediamine had been distilled off, the crude extract was acidified at pH 6 with 2 N HCl, then heated and filtered. After cooling, N-(2-nitrophenyl)ethylenediamine hydrochloride was collected as yellow needles. The yellow needles were then reduced with SnCl2 in aqueous HCl until there was no color visible. This solution was stewed for about 10 d, after which orange crystals suitable for data collection were obtained. 1H NMR (CDCl3): δ H1 (7.27, d, 1H), H4 (6.86, d, 1H), H5 (7.13, d, 1H), H6 (6.89, d, 1H), H7 (3.41, s, 2H), H8 (3.11, s, 2H), 13C NMR (CDCl3): δ C1 (137.46), C2 (127.57), C3 (111.56), C4 (121.29), C5 (116.69), C6 (115.01), C7 (37.44), C8 (35.41).

Refinement top

H atoms bonded to N1, N2, N3 and O1 were found in a difference map but were placed in calculated positions [N—H = 0.89 Å and Uiso(H) = 1.5Ueq(N) for the –N1H3 and –N3H3 H atoms; N—H = 0.862 Å and Uiso(H) = 1.5Ueq(N) for the –N2H H atoms] and were treated as riding [O—H = 1.046 Å and Uiso(H) = 2.76Ueq(O) for the O1H9 H atom, and O—H = 1.041 Å and Uiso(H) = 0.55Ueq(O) for the O1H10 H atom]. H atoms on C atoms were placed at calculated positions [C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C), and C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for the –CH2CH2– H atoms] and were treated as riding.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by small spheres of arbitrary radii.
2-(2-Ammoniophenylamino)ethanaminium hexachlorostannate(IV) monohydrate top
Crystal data top
(C8H15N3)[SnCl6]·H2OF(000) = 984
Mr = 502.64Dx = 1.952 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.2640 (17) ÅCell parameters from 3683 reflections
b = 22.960 (6) Åθ = 3.0–26.8°
c = 10.270 (2) ŵ = 2.43 mm1
β = 92.985 (3)°T = 293 K
V = 1710.6 (7) Å3Block, orange
Z = 40.3 × 0.2 × 0.2 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer
3011 independent reflections
Radiation source: oil sealed2653 reflections with I > 2σa(I)
Graphite monochromatorRint = 0.025
Detector resolution: 100x100 microns pixels mm-1θmax = 25.0°, θmin = 1.8°
ω scansh = 87
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2713
Tmin = 0.530, Tmax = 0.643l = 1211
6951 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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.032P)2 + 0.2954P]
where P = (Fo2 + 2Fc2)/3
3011 reflections(Δ/σ)max < 0.001
186 parametersΔρmax = 0.55 e Å3
3 restraintsΔρmin = 0.44 e Å3
Crystal data top
(C8H15N3)[SnCl6]·H2OV = 1710.6 (7) Å3
Mr = 502.64Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.2640 (17) ŵ = 2.43 mm1
b = 22.960 (6) ÅT = 293 K
c = 10.270 (2) Å0.3 × 0.2 × 0.2 mm
β = 92.985 (3)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
3011 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2653 reflections with I > 2σa(I)
Tmin = 0.530, Tmax = 0.643Rint = 0.025
6951 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0343 restraints
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.55 e Å3
3011 reflectionsΔρmin = 0.44 e Å3
186 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
xyzUiso*/Ueq
Sn10.14151 (3)0.163024 (12)0.49889 (2)0.03063 (10)
Cl10.08768 (15)0.13723 (6)0.65369 (11)0.0503 (3)
Cl20.38639 (14)0.14116 (5)0.66354 (10)0.0433 (3)
Cl30.14721 (16)0.06123 (5)0.43106 (11)0.0495 (3)
Cl40.37904 (14)0.18596 (6)0.34964 (10)0.0465 (3)
Cl50.09794 (14)0.18384 (5)0.33500 (10)0.0471 (3)
Cl60.13422 (17)0.26272 (5)0.57130 (11)0.0526 (3)
O10.8820 (6)0.5558 (2)0.0714 (4)0.0867 (13)
N10.6904 (5)0.49120 (16)0.2427 (3)0.0517 (10)
H1A0.56980.49220.22270.078*
H1B0.73200.45510.23220.078*
H1C0.74810.51530.19060.078*
N20.6800 (5)0.40960 (16)0.4421 (3)0.0411 (9)
N30.6453 (5)0.25960 (15)0.5761 (3)0.0473 (9)
H3A0.76130.25460.60620.071*
H3B0.60390.22690.53860.071*
H3C0.57550.26870.64180.071*
C10.7692 (6)0.5666 (2)0.4064 (5)0.0489 (12)
H10.77140.59380.33950.059*
C20.7257 (5)0.50921 (18)0.3791 (4)0.0352 (9)
C30.7217 (5)0.46645 (17)0.4746 (4)0.0331 (9)
C40.7645 (5)0.48447 (19)0.6024 (4)0.0398 (10)
H40.76360.45740.66960.048*
C50.8079 (6)0.5415 (2)0.6308 (5)0.0476 (12)
H50.83680.55220.71680.057*
C60.8093 (6)0.5831 (2)0.5337 (5)0.0532 (12)
H60.83700.62170.55400.064*
C70.6870 (6)0.36435 (19)0.5402 (4)0.0435 (11)
H7A0.60170.37340.60690.052*
H7B0.81010.36220.58120.052*
C80.6373 (7)0.3075 (2)0.4786 (4)0.0491 (12)
H8A0.72160.29910.41080.059*
H8B0.51380.30990.43820.059*
H20.596 (5)0.402 (3)0.382 (4)0.09 (2)*
H100.962 (5)0.5201 (12)0.101 (4)0.048 (13)*
H90.967 (11)0.591 (3)0.096 (8)0.24 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02967 (16)0.03594 (18)0.02606 (16)0.00128 (13)0.00050 (11)0.00046 (12)
Cl10.0405 (6)0.0688 (8)0.0425 (6)0.0024 (6)0.0105 (5)0.0101 (6)
Cl20.0374 (6)0.0548 (7)0.0368 (6)0.0005 (5)0.0069 (4)0.0085 (5)
Cl30.0582 (7)0.0381 (6)0.0517 (7)0.0026 (6)0.0031 (5)0.0067 (5)
Cl40.0405 (6)0.0660 (8)0.0334 (6)0.0103 (6)0.0059 (4)0.0026 (5)
Cl50.0413 (6)0.0604 (7)0.0382 (6)0.0041 (6)0.0108 (5)0.0017 (5)
Cl60.0617 (7)0.0399 (7)0.0553 (7)0.0013 (6)0.0052 (6)0.0105 (6)
O10.086 (3)0.077 (3)0.098 (3)0.024 (3)0.020 (2)0.012 (3)
N10.065 (3)0.047 (2)0.042 (2)0.000 (2)0.0023 (18)0.0123 (19)
N20.052 (2)0.037 (2)0.034 (2)0.0068 (18)0.0039 (17)0.0039 (17)
N30.054 (2)0.033 (2)0.054 (2)0.0055 (18)0.0024 (18)0.0001 (18)
C10.046 (3)0.040 (3)0.061 (3)0.008 (2)0.006 (2)0.007 (2)
C20.031 (2)0.039 (3)0.035 (2)0.0026 (19)0.0024 (17)0.0004 (19)
C30.033 (2)0.032 (2)0.035 (2)0.0049 (18)0.0047 (17)0.0010 (19)
C40.039 (2)0.042 (3)0.038 (2)0.003 (2)0.0030 (18)0.001 (2)
C50.042 (3)0.048 (3)0.052 (3)0.005 (2)0.001 (2)0.014 (2)
C60.050 (3)0.034 (3)0.076 (4)0.003 (2)0.007 (3)0.008 (3)
C70.057 (3)0.038 (3)0.036 (2)0.003 (2)0.000 (2)0.005 (2)
C80.064 (3)0.040 (3)0.043 (3)0.003 (2)0.003 (2)0.002 (2)
Geometric parameters (Å, º) top
Sn1—Cl52.4046 (11)N3—H3B0.8900
Sn1—Cl62.4082 (13)N3—H3C0.8900
Sn1—Cl42.4247 (11)C1—C61.378 (6)
Sn1—Cl12.4343 (11)C1—C21.380 (6)
Sn1—Cl32.4398 (13)C1—H10.9300
Sn1—Cl22.4418 (11)C2—C31.389 (5)
O1—H101.041 (10)C3—C41.395 (5)
O1—H91.046 (10)C4—C51.375 (6)
N1—C21.470 (5)C4—H40.9300
N1—H1A0.8900C5—C61.381 (6)
N1—H1B0.8900C5—H50.9300
N1—H1C0.8900C6—H60.9300
N2—C31.377 (5)C7—C81.486 (6)
N2—C71.446 (5)C7—H7A0.9700
N2—H20.862 (10)C7—H7B0.9700
N3—C81.487 (5)C8—H8A0.9700
N3—H3A0.8900C8—H8B0.9700
Cl5—Sn1—Cl690.03 (4)C6—C1—C2119.4 (4)
Cl5—Sn1—Cl491.54 (4)C6—C1—H1120.3
Cl6—Sn1—Cl490.95 (4)C2—C1—H1120.3
Cl5—Sn1—Cl190.64 (4)C1—C2—C3122.9 (4)
Cl6—Sn1—Cl190.15 (4)C1—C2—N1119.3 (4)
Cl4—Sn1—Cl1177.55 (4)C3—C2—N1117.7 (4)
Cl5—Sn1—Cl390.74 (4)N2—C3—C2120.7 (4)
Cl6—Sn1—Cl3178.55 (4)N2—C3—C4123.0 (4)
Cl4—Sn1—Cl390.25 (4)C2—C3—C4116.3 (4)
Cl1—Sn1—Cl388.61 (4)C5—C4—C3121.3 (4)
Cl5—Sn1—Cl2179.34 (4)C5—C4—H4119.3
Cl6—Sn1—Cl290.49 (4)C3—C4—H4119.3
Cl4—Sn1—Cl288.04 (4)C4—C5—C6121.0 (4)
Cl1—Sn1—Cl289.77 (4)C4—C5—H5119.5
Cl3—Sn1—Cl288.75 (4)C6—C5—H5119.5
H10—O1—H9103 (6)C1—C6—C5119.1 (5)
C2—N1—H1A109.5C1—C6—H6120.5
C2—N1—H1B109.5C5—C6—H6120.5
H1A—N1—H1B109.5N2—C7—C8109.6 (3)
C2—N1—H1C109.5N2—C7—H7A109.8
H1A—N1—H1C109.5C8—C7—H7A109.8
H1B—N1—H1C109.5N2—C7—H7B109.8
C3—N2—C7120.8 (3)C8—C7—H7B109.8
C3—N2—H2120 (4)H7A—C7—H7B108.2
C7—N2—H2111 (4)C7—C8—N3111.3 (3)
C8—N3—H3A109.5C7—C8—H8A109.4
C8—N3—H3B109.5N3—C8—H8A109.4
H3A—N3—H3B109.5C7—C8—H8B109.4
C8—N3—H3C109.5N3—C8—H8B109.4
H3A—N3—H3C109.5H8A—C8—H8B108.0
H3B—N3—H3C109.5
C6—C1—C2—C30.6 (6)N2—C3—C4—C5179.1 (4)
C6—C1—C2—N1177.5 (4)C2—C3—C4—C50.0 (6)
C7—N2—C3—C2176.1 (4)C3—C4—C5—C60.5 (6)
C7—N2—C3—C43.0 (6)C2—C1—C6—C51.0 (7)
C1—C2—C3—N2179.1 (4)C4—C5—C6—C11.0 (7)
N1—C2—C3—N22.1 (6)C3—N2—C7—C8179.6 (4)
C1—C2—C3—C40.0 (6)N2—C7—C8—N3179.3 (4)
N1—C2—C3—C4177.0 (3)

Experimental details

Crystal data
Chemical formula(C8H15N3)[SnCl6]·H2O
Mr502.64
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)7.2640 (17), 22.960 (6), 10.270 (2)
β (°) 92.985 (3)
V3)1710.6 (7)
Z4
Radiation typeMo Kα
µ (mm1)2.43
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.530, 0.643
No. of measured, independent and
observed [I > 2σa(I)] reflections
6951, 3011, 2653
Rint0.025
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.071, 1.07
No. of reflections3011
No. of parameters186
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.55, 0.44

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
Sn1—Cl52.4046 (11)Sn1—Cl22.4418 (11)
Sn1—Cl62.4082 (13)O1—H101.041 (10)
Sn1—Cl42.4247 (11)O1—H91.046 (10)
Sn1—Cl12.4343 (11)N2—H20.862 (10)
Sn1—Cl32.4398 (13)
Cl5—Sn1—Cl690.03 (4)Cl4—Sn1—Cl390.25 (4)
Cl5—Sn1—Cl491.54 (4)Cl1—Sn1—Cl388.61 (4)
Cl6—Sn1—Cl490.95 (4)Cl5—Sn1—Cl2179.34 (4)
Cl5—Sn1—Cl190.64 (4)Cl6—Sn1—Cl290.49 (4)
Cl6—Sn1—Cl190.15 (4)Cl4—Sn1—Cl288.04 (4)
Cl4—Sn1—Cl1177.55 (4)Cl1—Sn1—Cl289.77 (4)
Cl5—Sn1—Cl390.74 (4)Cl3—Sn1—Cl288.75 (4)
Cl6—Sn1—Cl3178.55 (4)C3—N2—C7120.8 (3)
C7—N2—C3—C2176.1 (4)N1—C2—C3—N22.1 (6)
C7—N2—C3—C43.0 (6)N2—C3—C4—C5179.1 (4)
C1—C2—C3—N2179.1 (4)N2—C7—C8—N3179.3 (4)
 

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