Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031467/hb2461sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031467/hb2461Isup2.hkl |
CCDC reference: 657518
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.078
- Data-to-parameter ratio = 20.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.82 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 100 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O1W .. 5.48 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 21 N2 -NI1 -N2 -C5 11.00 0.00 3.666 1.555 1.555 1.555 PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... O1<I>W< PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... O1<I>W< PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H1<I>N< PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.824 Tmax scaled 0.824 Tmin scaled 0.706 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To an ethanol solution (5 ml) of nickel chloride hexahydrate (0.119 g, 0.5 mmol) was added an ethanol solution (5 ml) of N,N-dimethyl-N'-ethyl-ethylenediamine (1.6 ml, 1 mmol). The solution was filtered. Ether was diffused into the filtrate; light blue crystals of (I) were isolated after a week.
The C-bound hydrogen atoms were placed at calculated positions in the riding model approximation [C—H = 0.93–0.98 Å, U(H) = 1.2–1.5 Ueq(C)]. The water and amino H atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H = N–H = 0.85±0.01 Å and free refinement of their Uiso values.
A number of nickel dichloride complexes of substituted ethylenediamines have been characterized by X-ray diffraction; these have the nickel atom chelated by two ligands. The octahedral geometry is completed by two water molecules. Such aquanickel salts are exemplified by the N,N-dimethylethylenediamine and N,N-diethylethylenediamine complexes (Ide & Norman, 2007; Ihara et al., 1991). The title compound, (I), shows a similar metal geometry (Fig. 1, Table 1). and the bite angle of the ligand is also similar to those found in such compounds. The components interact by way of N—H···Cl and O—H···Cl hydrogen bonds (Table 2).
For other nickel dichloride complexes of substituted ethylenediamines, see Ide & Norman (2007) and Ihara et al. (1991).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
Fig. 1. View of part of a chain in (I) showing 50% displacement ellipsoids for the non-hydrogen atoms. |
[Ni(C6H16N2)2(H2O)2]Cl2 | F(000) = 428 |
Mr = 398.06 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2782 reflections |
a = 7.802 (1) Å | θ = 2.6–27.5° |
b = 12.550 (1) Å | µ = 1.29 mm−1 |
c = 9.935 (1) Å | T = 295 K |
β = 95.750 (1)° | Block, light blue |
V = 967.9 (2) Å3 | 0.20 × 0.20 × 0.15 mm |
Z = 2 |
Bruker APEX CCD diffractometer | 2203 independent reflections |
Radiation source: fine-focus sealed tube | 1843 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.856, Tmax = 1.000 | k = −12→16 |
5912 measured reflections | l = −12→12 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0399P)2 + 0.2921P] where P = (Fo2 + 2Fc2)/3 |
2203 reflections | (Δ/σ)max = 0.001 |
109 parameters | Δρmax = 0.47 e Å−3 |
3 restraints | Δρmin = −0.36 e Å−3 |
[Ni(C6H16N2)2(H2O)2]Cl2 | V = 967.9 (2) Å3 |
Mr = 398.06 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.802 (1) Å | µ = 1.29 mm−1 |
b = 12.550 (1) Å | T = 295 K |
c = 9.935 (1) Å | 0.20 × 0.20 × 0.15 mm |
β = 95.750 (1)° |
Bruker APEX CCD diffractometer | 2203 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1843 reflections with I > 2σ(I) |
Tmin = 0.856, Tmax = 1.000 | Rint = 0.019 |
5912 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 3 restraints |
wR(F2) = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.47 e Å−3 |
2203 reflections | Δρmin = −0.36 e Å−3 |
109 parameters |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.02374 (11) | |
Cl1 | 0.02304 (6) | 0.31615 (4) | 0.44701 (7) | 0.05183 (18) | |
O1W | 0.23497 (17) | 0.52469 (12) | 0.44802 (15) | 0.0353 (3) | |
N1 | 0.4525 (2) | 0.33584 (12) | 0.46081 (17) | 0.0303 (3) | |
N2 | 0.5432 (2) | 0.50319 (12) | 0.28146 (16) | 0.0340 (4) | |
C1 | 0.4882 (3) | 0.14532 (19) | 0.5352 (3) | 0.0565 (6) | |
H1A | 0.5675 | 0.0980 | 0.5854 | 0.085* | |
H1B | 0.4670 | 0.1206 | 0.4436 | 0.085* | |
H1C | 0.3818 | 0.1470 | 0.5760 | 0.085* | |
C2 | 0.5644 (3) | 0.25613 (15) | 0.5361 (2) | 0.0415 (5) | |
H2A | 0.5879 | 0.2796 | 0.6291 | 0.050* | |
H2B | 0.6734 | 0.2531 | 0.4971 | 0.050* | |
C3 | 0.4438 (3) | 0.32060 (16) | 0.3122 (2) | 0.0431 (5) | |
H3A | 0.3294 | 0.3387 | 0.2712 | 0.052* | |
H3B | 0.4655 | 0.2464 | 0.2922 | 0.052* | |
C4 | 0.5748 (3) | 0.38971 (18) | 0.2536 (2) | 0.0441 (5) | |
H4A | 0.6894 | 0.3701 | 0.2927 | 0.053* | |
H4B | 0.5689 | 0.3785 | 0.1567 | 0.053* | |
C5 | 0.6964 (3) | 0.5649 (2) | 0.2497 (2) | 0.0560 (6) | |
H5A | 0.7056 | 0.5622 | 0.1541 | 0.084* | |
H5B | 0.7981 | 0.5347 | 0.2973 | 0.084* | |
H5C | 0.6846 | 0.6376 | 0.2771 | 0.084* | |
C6 | 0.3960 (3) | 0.5413 (2) | 0.1889 (2) | 0.0508 (6) | |
H6A | 0.4261 | 0.5397 | 0.0976 | 0.076* | |
H6B | 0.3681 | 0.6130 | 0.2125 | 0.076* | |
H6C | 0.2983 | 0.4960 | 0.1966 | 0.076* | |
H1W1 | 0.170 (3) | 0.4708 (13) | 0.448 (3) | 0.055 (8)* | |
H1W2 | 0.177 (3) | 0.5738 (14) | 0.478 (2) | 0.056 (8)* | |
H1N | 0.3539 (16) | 0.3279 (16) | 0.486 (2) | 0.034 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01999 (17) | 0.02258 (17) | 0.02879 (18) | 0.00071 (11) | 0.00310 (12) | −0.00120 (12) |
Cl1 | 0.0282 (3) | 0.0379 (3) | 0.0903 (5) | −0.0015 (2) | 0.0104 (3) | −0.0152 (3) |
O1W | 0.0237 (7) | 0.0315 (8) | 0.0510 (9) | 0.0016 (6) | 0.0045 (6) | −0.0039 (6) |
N1 | 0.0249 (8) | 0.0259 (8) | 0.0403 (9) | 0.0000 (6) | 0.0038 (6) | −0.0011 (6) |
N2 | 0.0353 (9) | 0.0365 (9) | 0.0304 (8) | −0.0016 (7) | 0.0047 (7) | 0.0004 (7) |
C1 | 0.0533 (15) | 0.0329 (12) | 0.0823 (18) | −0.0003 (10) | 0.0025 (13) | 0.0111 (11) |
C2 | 0.0350 (11) | 0.0296 (10) | 0.0581 (14) | 0.0022 (8) | −0.0045 (9) | 0.0015 (9) |
C3 | 0.0523 (13) | 0.0337 (11) | 0.0427 (12) | −0.0035 (9) | 0.0016 (10) | −0.0100 (9) |
C4 | 0.0495 (13) | 0.0461 (13) | 0.0377 (12) | 0.0050 (10) | 0.0099 (9) | −0.0077 (9) |
C5 | 0.0536 (14) | 0.0733 (18) | 0.0436 (13) | −0.0183 (13) | 0.0171 (11) | 0.0022 (12) |
C6 | 0.0577 (15) | 0.0583 (14) | 0.0351 (12) | 0.0045 (12) | −0.0010 (10) | 0.0042 (10) |
Ni1—O1W | 2.103 (1) | C1—H1B | 0.9600 |
Ni1—O1Wi | 2.103 (1) | C1—H1C | 0.9600 |
Ni1—N1 | 2.122 (2) | C2—H2A | 0.9700 |
Ni1—N1i | 2.122 (2) | C2—H2B | 0.9700 |
Ni1—N2 | 2.231 (2) | C3—C4 | 1.501 (3) |
Ni1—N2i | 2.231 (2) | C3—H3A | 0.9700 |
O1W—H1W1 | 0.84 (1) | C3—H3B | 0.9700 |
O1W—H1W2 | 0.84 (1) | C4—H4A | 0.9700 |
N1—C2 | 1.480 (2) | C4—H4B | 0.9700 |
N1—C3 | 1.484 (3) | C5—H5A | 0.9600 |
N1—H1N | 0.84 (1) | C5—H5B | 0.9600 |
N2—C4 | 1.476 (3) | C5—H5C | 0.9600 |
N2—C6 | 1.477 (3) | C6—H6A | 0.9600 |
N2—C5 | 1.484 (3) | C6—H6B | 0.9600 |
C1—C2 | 1.512 (3) | C6—H6C | 0.9600 |
C1—H1A | 0.9600 | ||
O1Wi—Ni1—O1W | 180.0 | C2—C1—H1C | 109.5 |
O1Wi—Ni1—N1 | 92.95 (6) | H1A—C1—H1C | 109.5 |
O1W—Ni1—N1 | 87.05 (6) | H1B—C1—H1C | 109.5 |
O1Wi—Ni1—N1i | 87.05 (6) | N1—C2—C1 | 114.00 (17) |
O1W—Ni1—N1i | 92.95 (6) | N1—C2—H2A | 108.8 |
N1—Ni1—N1i | 180.0 | C1—C2—H2A | 108.8 |
O1Wi—Ni1—N2 | 90.05 (6) | N1—C2—H2B | 108.8 |
O1W—Ni1—N2 | 89.95 (6) | C1—C2—H2B | 108.8 |
N1—Ni1—N2 | 83.08 (6) | H2A—C2—H2B | 107.6 |
N1i—Ni1—N2 | 96.92 (6) | N1—C3—C4 | 110.26 (16) |
O1Wi—Ni1—N2i | 89.95 (6) | N1—C3—H3A | 109.6 |
O1W—Ni1—N2i | 90.05 (6) | C4—C3—H3A | 109.6 |
N1—Ni1—N2i | 96.92 (6) | N1—C3—H3B | 109.6 |
N1i—Ni1—N2i | 83.08 (6) | C4—C3—H3B | 109.6 |
N2—Ni1—N2i | 180.0 | H3A—C3—H3B | 108.1 |
Ni1—O1W—H1W1 | 116.9 (18) | N2—C4—C3 | 110.61 (17) |
Ni1—O1W—H1W2 | 125.3 (17) | N2—C4—H4A | 109.5 |
H1W1—O1W—H1W2 | 104 (3) | C3—C4—H4A | 109.5 |
C2—N1—C3 | 112.42 (16) | N2—C4—H4B | 109.5 |
C2—N1—Ni1 | 118.68 (13) | C3—C4—H4B | 109.5 |
C3—N1—Ni1 | 107.30 (12) | H4A—C4—H4B | 108.1 |
C2—N1—H1N | 106.3 (14) | N2—C5—H5A | 109.5 |
C3—N1—H1N | 109.3 (15) | N2—C5—H5B | 109.5 |
Ni1—N1—H1N | 102.1 (14) | H5A—C5—H5B | 109.5 |
C4—N2—C6 | 109.24 (17) | N2—C5—H5C | 109.5 |
C4—N2—C5 | 108.09 (17) | H5A—C5—H5C | 109.5 |
C6—N2—C5 | 106.93 (18) | H5B—C5—H5C | 109.5 |
C4—N2—Ni1 | 102.09 (12) | N2—C6—H6A | 109.5 |
C6—N2—Ni1 | 115.32 (13) | N2—C6—H6B | 109.5 |
C5—N2—Ni1 | 114.83 (13) | H6A—C6—H6B | 109.5 |
C2—C1—H1A | 109.5 | N2—C6—H6C | 109.5 |
C2—C1—H1B | 109.5 | H6A—C6—H6C | 109.5 |
H1A—C1—H1B | 109.5 | H6B—C6—H6C | 109.5 |
O1Wi—Ni1—N1—C2 | 29.32 (15) | N1i—Ni1—N2—C6 | −80.96 (15) |
O1W—Ni1—N1—C2 | −150.68 (15) | O1Wi—Ni1—N2—C5 | −42.98 (16) |
N2—Ni1—N1—C2 | 119.01 (15) | O1W—Ni1—N2—C5 | 137.02 (16) |
N2i—Ni1—N1—C2 | −60.99 (15) | N1—Ni1—N2—C5 | −135.94 (16) |
O1Wi—Ni1—N1—C3 | −99.41 (13) | N1i—Ni1—N2—C5 | 44.06 (16) |
O1W—Ni1—N1—C3 | 80.59 (13) | N2i—Ni1—N2—C5 | 114 (100) |
N2—Ni1—N1—C3 | −9.72 (13) | C3—N1—C2—C1 | −72.2 (2) |
N2i—Ni1—N1—C3 | 170.28 (13) | Ni1—N1—C2—C1 | 161.47 (17) |
O1Wi—Ni1—N2—C4 | 73.70 (13) | C2—N1—C3—C4 | −94.2 (2) |
O1W—Ni1—N2—C4 | −106.30 (13) | Ni1—N1—C3—C4 | 38.0 (2) |
N1—Ni1—N2—C4 | −19.27 (12) | C6—N2—C4—C3 | −76.6 (2) |
N1i—Ni1—N2—C4 | 160.74 (12) | C5—N2—C4—C3 | 167.39 (18) |
O1Wi—Ni1—N2—C6 | −168.00 (15) | Ni1—N2—C4—C3 | 45.94 (19) |
O1W—Ni1—N2—C6 | 12.00 (15) | N1—C3—C4—N2 | −59.9 (2) |
N1—Ni1—N2—C6 | 99.04 (15) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···Cl1 | 0.84 (1) | 2.26 (1) | 3.095 (2) | 174 (2) |
O1W—H1W2···Cl1ii | 0.84 (1) | 2.26 (1) | 3.090 (2) | 169 (2) |
N1—H1N···Cl1 | 0.84 (1) | 2.58 (1) | 3.349 (2) | 154 (2) |
Symmetry code: (ii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C6H16N2)2(H2O)2]Cl2 |
Mr | 398.06 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 7.802 (1), 12.550 (1), 9.935 (1) |
β (°) | 95.750 (1) |
V (Å3) | 967.9 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.29 |
Crystal size (mm) | 0.20 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.856, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5912, 2203, 1843 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.078, 1.04 |
No. of reflections | 2203 |
No. of parameters | 109 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.47, −0.36 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···Cl1 | 0.84 (1) | 2.26 (1) | 3.095 (2) | 174 (2) |
O1W—H1W2···Cl1i | 0.84 (1) | 2.26 (1) | 3.090 (2) | 169 (2) |
N1—H1N···Cl1 | 0.84 (1) | 2.58 (1) | 3.349 (2) | 154 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
A number of nickel dichloride complexes of substituted ethylenediamines have been characterized by X-ray diffraction; these have the nickel atom chelated by two ligands. The octahedral geometry is completed by two water molecules. Such aquanickel salts are exemplified by the N,N-dimethylethylenediamine and N,N-diethylethylenediamine complexes (Ide & Norman, 2007; Ihara et al., 1991). The title compound, (I), shows a similar metal geometry (Fig. 1, Table 1). and the bite angle of the ligand is also similar to those found in such compounds. The components interact by way of N—H···Cl and O—H···Cl hydrogen bonds (Table 2).