Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029454/fl6183sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029454/fl6183Isup2.hkl |
CCDC reference: 287555
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
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.
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.
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. |
(C8H15N3)[SnCl6]·H2O | F(000) = 984 |
Mr = 502.64 | Dx = 1.952 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2640 (17) Å | Cell parameters from 3683 reflections |
b = 22.960 (6) Å | θ = 3.0–26.8° |
c = 10.270 (2) Å | µ = 2.43 mm−1 |
β = 92.985 (3)° | T = 293 K |
V = 1710.6 (7) Å3 | Block, orange |
Z = 4 | 0.3 × 0.2 × 0.2 mm |
Bruker APEX CCD area-detector diffractometer | 3011 independent reflections |
Radiation source: oil sealed | 2653 reflections with I > 2σa(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 100x100 microns pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −8→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −27→13 |
Tmin = 0.530, Tmax = 0.643 | l = −12→11 |
6951 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H 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 parameters | Δρmax = 0.55 e Å−3 |
3 restraints | Δρmin = −0.44 e Å−3 |
(C8H15N3)[SnCl6]·H2O | V = 1710.6 (7) Å3 |
Mr = 502.64 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.2640 (17) Å | µ = 2.43 mm−1 |
b = 22.960 (6) Å | T = 293 K |
c = 10.270 (2) Å | 0.3 × 0.2 × 0.2 mm |
β = 92.985 (3)° |
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 = 0.643 | Rint = 0.025 |
6951 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 3 restraints |
wR(F2) = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.55 e Å−3 |
3011 reflections | Δρmin = −0.44 e Å−3 |
186 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.14151 (3) | 0.163024 (12) | 0.49889 (2) | 0.03063 (10) | |
Cl1 | −0.08768 (15) | 0.13723 (6) | 0.65369 (11) | 0.0503 (3) | |
Cl2 | 0.38639 (14) | 0.14116 (5) | 0.66354 (10) | 0.0433 (3) | |
Cl3 | 0.14721 (16) | 0.06123 (5) | 0.43106 (11) | 0.0495 (3) | |
Cl4 | 0.37904 (14) | 0.18596 (6) | 0.34964 (10) | 0.0465 (3) | |
Cl5 | −0.09794 (14) | 0.18384 (5) | 0.33500 (10) | 0.0471 (3) | |
Cl6 | 0.13422 (17) | 0.26272 (5) | 0.57130 (11) | 0.0526 (3) | |
O1 | 0.8820 (6) | 0.5558 (2) | 0.0714 (4) | 0.0867 (13) | |
N1 | 0.6904 (5) | 0.49120 (16) | 0.2427 (3) | 0.0517 (10) | |
H1A | 0.5698 | 0.4922 | 0.2227 | 0.078* | |
H1B | 0.7320 | 0.4551 | 0.2322 | 0.078* | |
H1C | 0.7481 | 0.5153 | 0.1906 | 0.078* | |
N2 | 0.6800 (5) | 0.40960 (16) | 0.4421 (3) | 0.0411 (9) | |
N3 | 0.6453 (5) | 0.25960 (15) | 0.5761 (3) | 0.0473 (9) | |
H3A | 0.7613 | 0.2546 | 0.6062 | 0.071* | |
H3B | 0.6039 | 0.2269 | 0.5386 | 0.071* | |
H3C | 0.5755 | 0.2687 | 0.6418 | 0.071* | |
C1 | 0.7692 (6) | 0.5666 (2) | 0.4064 (5) | 0.0489 (12) | |
H1 | 0.7714 | 0.5938 | 0.3395 | 0.059* | |
C2 | 0.7257 (5) | 0.50921 (18) | 0.3791 (4) | 0.0352 (9) | |
C3 | 0.7217 (5) | 0.46645 (17) | 0.4746 (4) | 0.0331 (9) | |
C4 | 0.7645 (5) | 0.48447 (19) | 0.6024 (4) | 0.0398 (10) | |
H4 | 0.7636 | 0.4574 | 0.6696 | 0.048* | |
C5 | 0.8079 (6) | 0.5415 (2) | 0.6308 (5) | 0.0476 (12) | |
H5 | 0.8368 | 0.5522 | 0.7168 | 0.057* | |
C6 | 0.8093 (6) | 0.5831 (2) | 0.5337 (5) | 0.0532 (12) | |
H6 | 0.8370 | 0.6217 | 0.5540 | 0.064* | |
C7 | 0.6870 (6) | 0.36435 (19) | 0.5402 (4) | 0.0435 (11) | |
H7A | 0.6017 | 0.3734 | 0.6069 | 0.052* | |
H7B | 0.8101 | 0.3622 | 0.5812 | 0.052* | |
C8 | 0.6373 (7) | 0.3075 (2) | 0.4786 (4) | 0.0491 (12) | |
H8A | 0.7216 | 0.2991 | 0.4108 | 0.059* | |
H8B | 0.5138 | 0.3099 | 0.4382 | 0.059* | |
H2 | 0.596 (5) | 0.402 (3) | 0.382 (4) | 0.09 (2)* | |
H10 | 0.962 (5) | 0.5201 (12) | 0.101 (4) | 0.048 (13)* | |
H9 | 0.967 (11) | 0.591 (3) | 0.096 (8) | 0.24 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02967 (16) | 0.03594 (18) | 0.02606 (16) | −0.00128 (13) | −0.00050 (11) | 0.00046 (12) |
Cl1 | 0.0405 (6) | 0.0688 (8) | 0.0425 (6) | −0.0024 (6) | 0.0105 (5) | 0.0101 (6) |
Cl2 | 0.0374 (6) | 0.0548 (7) | 0.0368 (6) | −0.0005 (5) | −0.0069 (4) | 0.0085 (5) |
Cl3 | 0.0582 (7) | 0.0381 (6) | 0.0517 (7) | −0.0026 (6) | −0.0031 (5) | −0.0067 (5) |
Cl4 | 0.0405 (6) | 0.0660 (8) | 0.0334 (6) | −0.0103 (6) | 0.0059 (4) | 0.0026 (5) |
Cl5 | 0.0413 (6) | 0.0604 (7) | 0.0382 (6) | 0.0041 (6) | −0.0108 (5) | 0.0017 (5) |
Cl6 | 0.0617 (7) | 0.0399 (7) | 0.0553 (7) | 0.0013 (6) | −0.0052 (6) | −0.0105 (6) |
O1 | 0.086 (3) | 0.077 (3) | 0.098 (3) | −0.024 (3) | 0.020 (2) | 0.012 (3) |
N1 | 0.065 (3) | 0.047 (2) | 0.042 (2) | 0.000 (2) | −0.0023 (18) | 0.0123 (19) |
N2 | 0.052 (2) | 0.037 (2) | 0.034 (2) | −0.0068 (18) | −0.0039 (17) | 0.0039 (17) |
N3 | 0.054 (2) | 0.033 (2) | 0.054 (2) | −0.0055 (18) | −0.0024 (18) | 0.0001 (18) |
C1 | 0.046 (3) | 0.040 (3) | 0.061 (3) | 0.008 (2) | 0.006 (2) | 0.007 (2) |
C2 | 0.031 (2) | 0.039 (3) | 0.035 (2) | 0.0026 (19) | 0.0024 (17) | −0.0004 (19) |
C3 | 0.033 (2) | 0.032 (2) | 0.035 (2) | 0.0049 (18) | 0.0047 (17) | 0.0010 (19) |
C4 | 0.039 (2) | 0.042 (3) | 0.038 (2) | 0.003 (2) | 0.0030 (18) | −0.001 (2) |
C5 | 0.042 (3) | 0.048 (3) | 0.052 (3) | 0.005 (2) | −0.001 (2) | −0.014 (2) |
C6 | 0.050 (3) | 0.034 (3) | 0.076 (4) | 0.003 (2) | 0.007 (3) | −0.008 (3) |
C7 | 0.057 (3) | 0.038 (3) | 0.036 (2) | −0.003 (2) | 0.000 (2) | 0.005 (2) |
C8 | 0.064 (3) | 0.040 (3) | 0.043 (3) | −0.003 (2) | −0.003 (2) | 0.002 (2) |
Sn1—Cl5 | 2.4046 (11) | N3—H3B | 0.8900 |
Sn1—Cl6 | 2.4082 (13) | N3—H3C | 0.8900 |
Sn1—Cl4 | 2.4247 (11) | C1—C6 | 1.378 (6) |
Sn1—Cl1 | 2.4343 (11) | C1—C2 | 1.380 (6) |
Sn1—Cl3 | 2.4398 (13) | C1—H1 | 0.9300 |
Sn1—Cl2 | 2.4418 (11) | C2—C3 | 1.389 (5) |
O1—H10 | 1.041 (10) | C3—C4 | 1.395 (5) |
O1—H9 | 1.046 (10) | C4—C5 | 1.375 (6) |
N1—C2 | 1.470 (5) | C4—H4 | 0.9300 |
N1—H1A | 0.8900 | C5—C6 | 1.381 (6) |
N1—H1B | 0.8900 | C5—H5 | 0.9300 |
N1—H1C | 0.8900 | C6—H6 | 0.9300 |
N2—C3 | 1.377 (5) | C7—C8 | 1.486 (6) |
N2—C7 | 1.446 (5) | C7—H7A | 0.9700 |
N2—H2 | 0.862 (10) | C7—H7B | 0.9700 |
N3—C8 | 1.487 (5) | C8—H8A | 0.9700 |
N3—H3A | 0.8900 | C8—H8B | 0.9700 |
Cl5—Sn1—Cl6 | 90.03 (4) | C6—C1—C2 | 119.4 (4) |
Cl5—Sn1—Cl4 | 91.54 (4) | C6—C1—H1 | 120.3 |
Cl6—Sn1—Cl4 | 90.95 (4) | C2—C1—H1 | 120.3 |
Cl5—Sn1—Cl1 | 90.64 (4) | C1—C2—C3 | 122.9 (4) |
Cl6—Sn1—Cl1 | 90.15 (4) | C1—C2—N1 | 119.3 (4) |
Cl4—Sn1—Cl1 | 177.55 (4) | C3—C2—N1 | 117.7 (4) |
Cl5—Sn1—Cl3 | 90.74 (4) | N2—C3—C2 | 120.7 (4) |
Cl6—Sn1—Cl3 | 178.55 (4) | N2—C3—C4 | 123.0 (4) |
Cl4—Sn1—Cl3 | 90.25 (4) | C2—C3—C4 | 116.3 (4) |
Cl1—Sn1—Cl3 | 88.61 (4) | C5—C4—C3 | 121.3 (4) |
Cl5—Sn1—Cl2 | 179.34 (4) | C5—C4—H4 | 119.3 |
Cl6—Sn1—Cl2 | 90.49 (4) | C3—C4—H4 | 119.3 |
Cl4—Sn1—Cl2 | 88.04 (4) | C4—C5—C6 | 121.0 (4) |
Cl1—Sn1—Cl2 | 89.77 (4) | C4—C5—H5 | 119.5 |
Cl3—Sn1—Cl2 | 88.75 (4) | C6—C5—H5 | 119.5 |
H10—O1—H9 | 103 (6) | C1—C6—C5 | 119.1 (5) |
C2—N1—H1A | 109.5 | C1—C6—H6 | 120.5 |
C2—N1—H1B | 109.5 | C5—C6—H6 | 120.5 |
H1A—N1—H1B | 109.5 | N2—C7—C8 | 109.6 (3) |
C2—N1—H1C | 109.5 | N2—C7—H7A | 109.8 |
H1A—N1—H1C | 109.5 | C8—C7—H7A | 109.8 |
H1B—N1—H1C | 109.5 | N2—C7—H7B | 109.8 |
C3—N2—C7 | 120.8 (3) | C8—C7—H7B | 109.8 |
C3—N2—H2 | 120 (4) | H7A—C7—H7B | 108.2 |
C7—N2—H2 | 111 (4) | C7—C8—N3 | 111.3 (3) |
C8—N3—H3A | 109.5 | C7—C8—H8A | 109.4 |
C8—N3—H3B | 109.5 | N3—C8—H8A | 109.4 |
H3A—N3—H3B | 109.5 | C7—C8—H8B | 109.4 |
C8—N3—H3C | 109.5 | N3—C8—H8B | 109.4 |
H3A—N3—H3C | 109.5 | H8A—C8—H8B | 108.0 |
H3B—N3—H3C | 109.5 | ||
C6—C1—C2—C3 | −0.6 (6) | N2—C3—C4—C5 | 179.1 (4) |
C6—C1—C2—N1 | −177.5 (4) | C2—C3—C4—C5 | 0.0 (6) |
C7—N2—C3—C2 | 176.1 (4) | C3—C4—C5—C6 | 0.5 (6) |
C7—N2—C3—C4 | −3.0 (6) | C2—C1—C6—C5 | 1.0 (7) |
C1—C2—C3—N2 | −179.1 (4) | C4—C5—C6—C1 | −1.0 (7) |
N1—C2—C3—N2 | −2.1 (6) | C3—N2—C7—C8 | −179.6 (4) |
C1—C2—C3—C4 | 0.0 (6) | N2—C7—C8—N3 | 179.3 (4) |
N1—C2—C3—C4 | 177.0 (3) |
Experimental details
Crystal data | |
Chemical formula | (C8H15N3)[SnCl6]·H2O |
Mr | 502.64 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 7.2640 (17), 22.960 (6), 10.270 (2) |
β (°) | 92.985 (3) |
V (Å3) | 1710.6 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.43 |
Crystal size (mm) | 0.3 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.530, 0.643 |
No. of measured, independent and observed [I > 2σa(I)] reflections | 6951, 3011, 2653 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.071, 1.07 |
No. of reflections | 3011 |
No. of parameters | 186 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.55, −0.44 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
Sn1—Cl5 | 2.4046 (11) | Sn1—Cl2 | 2.4418 (11) |
Sn1—Cl6 | 2.4082 (13) | O1—H10 | 1.041 (10) |
Sn1—Cl4 | 2.4247 (11) | O1—H9 | 1.046 (10) |
Sn1—Cl1 | 2.4343 (11) | N2—H2 | 0.862 (10) |
Sn1—Cl3 | 2.4398 (13) | ||
Cl5—Sn1—Cl6 | 90.03 (4) | Cl4—Sn1—Cl3 | 90.25 (4) |
Cl5—Sn1—Cl4 | 91.54 (4) | Cl1—Sn1—Cl3 | 88.61 (4) |
Cl6—Sn1—Cl4 | 90.95 (4) | Cl5—Sn1—Cl2 | 179.34 (4) |
Cl5—Sn1—Cl1 | 90.64 (4) | Cl6—Sn1—Cl2 | 90.49 (4) |
Cl6—Sn1—Cl1 | 90.15 (4) | Cl4—Sn1—Cl2 | 88.04 (4) |
Cl4—Sn1—Cl1 | 177.55 (4) | Cl1—Sn1—Cl2 | 89.77 (4) |
Cl5—Sn1—Cl3 | 90.74 (4) | Cl3—Sn1—Cl2 | 88.75 (4) |
Cl6—Sn1—Cl3 | 178.55 (4) | C3—N2—C7 | 120.8 (3) |
C7—N2—C3—C2 | 176.1 (4) | N1—C2—C3—N2 | −2.1 (6) |
C7—N2—C3—C4 | −3.0 (6) | N2—C3—C4—C5 | 179.1 (4) |
C1—C2—C3—N2 | −179.1 (4) | N2—C7—C8—N3 | 179.3 (4) |
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.