In the title controsymmetric mononuclear nickel(II) compound, [Ni(C
13H
19N
3O
3)
2(NCS)
2]·2H
2O, the Ni
II atom lies on an inversion centre and is six-coordinated by two phenolate O and two imine N atoms from two Schiff base ligands, and by two terminal N atoms from two thiocyanate anions, forming an octahedral coordination. In the crystal structure, molecules are linked through intermolecular O—H
O, O—H
N and N—H
O hydrogen bonds, forming chains running along [101].
Supporting information
CCDC reference: 605025
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.095
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - C14 .. 8.88 su
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C14 .. 6.05 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N4 .. 6.05 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Bis{2-[2-(diethylamino)ethyliminomethyl]-4-
nitrophenolato}dithiocyanatonickel(II) dihydrate
top
Crystal data top
[Ni(C13H19N3O3)2(NCS)2]·2H2O | F(000) = 780 |
Mr = 741.53 | Dx = 1.443 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5943 reflections |
a = 6.909 (1) Å | θ = 2.6–27.8° |
b = 20.183 (2) Å | µ = 0.75 mm−1 |
c = 12.554 (1) Å | T = 298 K |
β = 102.84 (1)° | Block, green |
V = 1706.8 (3) Å3 | 0.27 × 0.23 × 0.20 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4052 independent reflections |
Radiation source: fine-focus sealed tube | 3459 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.823, Tmax = 0.865 | k = −25→26 |
14641 measured reflections | l = −16→16 |
Refinement top
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0481P)2 + 0.596P] where P = (Fo2 + 2Fc2)/3 |
4052 reflections | (Δ/σ)max = 0.001 |
225 parameters | Δρmax = 0.45 e Å−3 |
4 restraints | Δρmin = −0.35 e Å−3 |
Special details top
Experimental. IR (cm-1): 3472.3 (b, w), 3022.2 (m), 2923.8 (m),
2847.3 (m), (2093.5 (vs), 1634.6 (s), 1547.2 (m),
1472.3 (m), 1443.4 (m), 1301.4 (m), 1186.7 (w),
1148.4 (w), 771.5 (m), 588.7 (w), 514.7 (w). |
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 | x | y | z | Uiso*/Ueq | |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.02716 (10) | |
S1 | 0.23801 (9) | 0.70227 (3) | 0.61950 (6) | 0.0631 (2) | |
O1 | 0.23232 (18) | 0.48792 (7) | 0.39629 (10) | 0.0360 (3) | |
O2 | 0.1988 (3) | 0.41600 (10) | −0.08985 (13) | 0.0761 (6) | |
O3 | −0.0896 (3) | 0.38283 (11) | −0.07308 (14) | 0.0830 (6) | |
O4 | 0.2410 (2) | 0.63782 (8) | 0.30795 (13) | 0.0521 (4) | |
N1 | 0.6056 (2) | 0.53314 (7) | 0.36431 (11) | 0.0303 (3) | |
N2 | 0.6467 (2) | 0.68143 (8) | 0.38610 (12) | 0.0356 (3) | |
N3 | 0.0729 (3) | 0.40807 (9) | −0.03534 (14) | 0.0540 (5) | |
N4 | 0.4069 (2) | 0.59411 (8) | 0.53782 (13) | 0.0402 (4) | |
C1 | 0.3424 (3) | 0.48005 (9) | 0.22910 (14) | 0.0324 (4) | |
C2 | 0.2027 (3) | 0.46871 (9) | 0.29651 (13) | 0.0314 (4) | |
C3 | 0.0223 (3) | 0.43647 (10) | 0.24772 (16) | 0.0410 (4) | |
H3 | −0.0701 | 0.4283 | 0.2899 | 0.049* | |
C4 | −0.0201 (3) | 0.41714 (10) | 0.14128 (16) | 0.0454 (5) | |
H4 | −0.1397 | 0.3961 | 0.1115 | 0.054* | |
C5 | 0.1174 (3) | 0.42906 (9) | 0.07699 (14) | 0.0415 (4) | |
C6 | 0.2945 (3) | 0.45995 (9) | 0.12050 (15) | 0.0395 (4) | |
H6 | 0.3841 | 0.4676 | 0.0764 | 0.047* | |
C7 | 0.5292 (3) | 0.51451 (9) | 0.26655 (15) | 0.0341 (4) | |
H7 | 0.6011 | 0.5241 | 0.2140 | 0.041* | |
C8 | 0.7974 (3) | 0.56740 (9) | 0.38112 (15) | 0.0359 (4) | |
H8A | 0.8283 | 0.5761 | 0.3107 | 0.043* | |
H8B | 0.9004 | 0.5388 | 0.4221 | 0.043* | |
C9 | 0.7972 (3) | 0.63194 (9) | 0.44179 (15) | 0.0370 (4) | |
H9A | 0.7730 | 0.6225 | 0.5135 | 0.044* | |
H9B | 0.9281 | 0.6517 | 0.4523 | 0.044* | |
C10 | 0.6730 (3) | 0.70248 (11) | 0.27530 (17) | 0.0493 (5) | |
H10A | 0.6815 | 0.6632 | 0.2320 | 0.059* | |
H10B | 0.5565 | 0.7272 | 0.2390 | 0.059* | |
C11 | 0.8538 (4) | 0.74437 (15) | 0.2787 (2) | 0.0722 (8) | |
H11A | 0.8353 | 0.7870 | 0.3088 | 0.108* | |
H11B | 0.8742 | 0.7497 | 0.2060 | 0.108* | |
H11C | 0.9676 | 0.7231 | 0.3235 | 0.108* | |
C12 | 0.6428 (3) | 0.73880 (11) | 0.46262 (18) | 0.0493 (5) | |
H12A | 0.6216 | 0.7218 | 0.5314 | 0.059* | |
H12B | 0.7712 | 0.7605 | 0.4773 | 0.059* | |
C13 | 0.4855 (4) | 0.78914 (13) | 0.4195 (2) | 0.0683 (7) | |
H13A | 0.5159 | 0.8109 | 0.3572 | 0.102* | |
H13B | 0.4809 | 0.8213 | 0.4752 | 0.102* | |
H13C | 0.3591 | 0.7675 | 0.3983 | 0.102* | |
C14 | 0.3370 (3) | 0.63830 (10) | 0.57258 (14) | 0.0360 (4) | |
H4A | 0.190 (4) | 0.6332 (13) | 0.2406 (9) | 0.080* | |
H4B | 0.229 (4) | 0.6018 (9) | 0.3402 (19) | 0.080* | |
H2 | 0.524 (2) | 0.6643 (13) | 0.371 (2) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.02660 (16) | 0.03246 (17) | 0.02272 (15) | 0.00116 (11) | 0.00613 (11) | 0.00100 (11) |
S1 | 0.0438 (3) | 0.0651 (4) | 0.0817 (4) | −0.0045 (3) | 0.0170 (3) | −0.0418 (3) |
O1 | 0.0293 (6) | 0.0525 (8) | 0.0260 (6) | 0.0000 (5) | 0.0061 (5) | −0.0011 (5) |
O2 | 0.1092 (16) | 0.0876 (13) | 0.0354 (9) | −0.0134 (12) | 0.0246 (9) | −0.0144 (8) |
O3 | 0.1023 (15) | 0.0930 (15) | 0.0444 (9) | −0.0352 (12) | −0.0037 (10) | −0.0206 (9) |
O4 | 0.0477 (9) | 0.0556 (9) | 0.0469 (9) | 0.0010 (7) | −0.0023 (7) | −0.0033 (7) |
N1 | 0.0306 (7) | 0.0313 (7) | 0.0303 (7) | 0.0016 (6) | 0.0100 (6) | 0.0018 (6) |
N2 | 0.0324 (8) | 0.0399 (8) | 0.0332 (8) | −0.0052 (6) | 0.0050 (6) | −0.0024 (6) |
N3 | 0.0832 (14) | 0.0444 (10) | 0.0305 (9) | −0.0041 (10) | 0.0040 (9) | −0.0043 (7) |
N4 | 0.0462 (9) | 0.0373 (8) | 0.0386 (8) | 0.0035 (7) | 0.0127 (7) | 0.0006 (7) |
C1 | 0.0383 (9) | 0.0331 (8) | 0.0266 (8) | 0.0004 (7) | 0.0087 (7) | 0.0007 (6) |
C2 | 0.0341 (9) | 0.0317 (9) | 0.0276 (8) | 0.0038 (7) | 0.0051 (7) | 0.0036 (6) |
C3 | 0.0387 (10) | 0.0469 (11) | 0.0372 (10) | −0.0057 (8) | 0.0082 (8) | −0.0005 (8) |
C4 | 0.0493 (12) | 0.0439 (11) | 0.0388 (10) | −0.0083 (9) | 0.0010 (9) | −0.0044 (8) |
C5 | 0.0591 (13) | 0.0363 (10) | 0.0265 (9) | −0.0008 (8) | 0.0037 (8) | −0.0029 (7) |
C6 | 0.0512 (11) | 0.0394 (10) | 0.0296 (9) | 0.0002 (8) | 0.0128 (8) | 0.0009 (7) |
C7 | 0.0364 (9) | 0.0385 (9) | 0.0304 (9) | 0.0016 (7) | 0.0138 (7) | 0.0024 (7) |
C8 | 0.0280 (9) | 0.0452 (10) | 0.0352 (9) | 0.0004 (7) | 0.0083 (7) | 0.0065 (8) |
C9 | 0.0326 (9) | 0.0447 (10) | 0.0303 (9) | −0.0072 (7) | −0.0003 (7) | 0.0051 (7) |
C10 | 0.0600 (13) | 0.0525 (12) | 0.0346 (10) | 0.0090 (10) | 0.0086 (9) | 0.0072 (9) |
C11 | 0.0729 (18) | 0.0764 (18) | 0.0758 (18) | 0.0004 (14) | 0.0348 (14) | 0.0270 (14) |
C12 | 0.0532 (13) | 0.0464 (12) | 0.0494 (12) | −0.0108 (9) | 0.0140 (10) | −0.0128 (9) |
C13 | 0.0735 (17) | 0.0532 (14) | 0.0793 (18) | 0.0067 (12) | 0.0195 (14) | −0.0140 (13) |
C14 | 0.0309 (9) | 0.0451 (10) | 0.0316 (9) | −0.0070 (7) | 0.0060 (7) | −0.0033 (7) |
Geometric parameters (Å, º) top
Ni1—O1 | 2.026 (2) | C3—C4 | 1.360 (3) |
Ni1—O1i | 2.026 (2) | C3—H3 | 0.93 |
Ni1—N4i | 2.093 (2) | C4—C5 | 1.397 (3) |
Ni1—N4 | 2.093 (2) | C4—H4 | 0.93 |
Ni1—N1 | 2.106 (2) | C5—C6 | 1.374 (3) |
Ni1—N1i | 2.106 (2) | C6—H6 | 0.93 |
S1—C14 | 1.631 (2) | C7—H7 | 0.93 |
O1—C2 | 1.283 (2) | C8—C9 | 1.509 (3) |
O2—N3 | 1.231 (3) | C8—H8A | 0.97 |
O3—N3 | 1.228 (3) | C8—H8B | 0.97 |
O4—H4A | 0.846 (10) | C9—H9A | 0.97 |
O4—H4B | 0.845 (10) | C9—H9B | 0.97 |
N1—C7 | 1.280 (2) | C10—C11 | 1.501 (4) |
N1—C8 | 1.468 (2) | C10—H10A | 0.97 |
N2—C9 | 1.498 (2) | C10—H10B | 0.97 |
N2—C10 | 1.504 (3) | C11—H11A | 0.96 |
N2—C12 | 1.509 (3) | C11—H11B | 0.96 |
N2—H2 | 0.898 (10) | C11—H11C | 0.96 |
N3—C5 | 1.439 (2) | C12—C13 | 1.498 (3) |
N4—C14 | 1.146 (2) | C12—H12A | 0.97 |
C1—C6 | 1.390 (2) | C12—H12B | 0.97 |
C1—C2 | 1.437 (2) | C13—H13A | 0.96 |
C1—C7 | 1.449 (3) | C13—H13B | 0.96 |
C2—C3 | 1.419 (3) | C13—H13C | 0.96 |
| | | |
O1—Ni1—O1i | 180 | C4—C5—N3 | 119.42 (19) |
O1—Ni1—N4i | 91.59 (6) | C5—C6—C1 | 121.27 (18) |
O1i—Ni1—N4i | 88.41 (6) | C5—C6—H6 | 119.4 |
O1—Ni1—N4 | 88.41 (6) | C1—C6—H6 | 119.4 |
O1i—Ni1—N4 | 91.59 (6) | N1—C7—C1 | 126.88 (16) |
N4i—Ni1—N4 | 180 | N1—C7—H7 | 116.6 |
O1—Ni1—N1 | 87.10 (6) | C1—C7—H7 | 116.6 |
O1i—Ni1—N1 | 92.90 (6) | N1—C8—C9 | 112.16 (15) |
N4i—Ni1—N1 | 85.73 (6) | N1—C8—H8A | 109.2 |
N4—Ni1—N1 | 94.27 (6) | C9—C8—H8A | 109.2 |
O1—Ni1—N1i | 92.90 (6) | N1—C8—H8B | 109.2 |
O1i—Ni1—N1i | 87.10 (6) | C9—C8—H8B | 109.2 |
N4i—Ni1—N1i | 94.27 (6) | H8A—C8—H8B | 107.9 |
N4—Ni1—N1i | 85.73 (6) | N2—C9—C8 | 114.73 (15) |
N1—Ni1—N1i | 180 | N2—C9—H9A | 108.6 |
C2—O1—Ni1 | 126.05 (12) | C8—C9—H9A | 108.6 |
H4A—O4—H4B | 109 (2) | N2—C9—H9B | 108.6 |
C7—N1—C8 | 116.32 (15) | C8—C9—H9B | 108.6 |
C7—N1—Ni1 | 122.60 (12) | H9A—C9—H9B | 107.6 |
C8—N1—Ni1 | 119.83 (11) | C11—C10—N2 | 113.80 (19) |
C9—N2—C10 | 113.95 (15) | C11—C10—H10A | 108.8 |
C9—N2—C12 | 108.86 (15) | N2—C10—H10A | 108.8 |
C10—N2—C12 | 113.28 (16) | C11—C10—H10B | 108.8 |
C9—N2—H2 | 111.5 (19) | N2—C10—H10B | 108.8 |
C10—N2—H2 | 102.9 (18) | H10A—C10—H10B | 107.7 |
C12—N2—H2 | 106.0 (19) | C10—C11—H11A | 109.5 |
O3—N3—O2 | 122.5 (2) | C10—C11—H11B | 109.5 |
O3—N3—C5 | 118.5 (2) | H11A—C11—H11B | 109.5 |
O2—N3—C5 | 118.9 (2) | C10—C11—H11C | 109.5 |
C14—N4—Ni1 | 165.79 (16) | H11A—C11—H11C | 109.5 |
C6—C1—C2 | 119.12 (17) | H11B—C11—H11C | 109.5 |
C6—C1—C7 | 117.32 (17) | C13—C12—N2 | 113.85 (19) |
C2—C1—C7 | 123.49 (16) | C13—C12—H12A | 108.8 |
O1—C2—C3 | 119.62 (16) | N2—C12—H12A | 108.8 |
O1—C2—C1 | 122.99 (16) | C13—C12—H12B | 108.8 |
C3—C2—C1 | 117.36 (16) | N2—C12—H12B | 108.8 |
C4—C3—C2 | 122.16 (19) | H12A—C12—H12B | 107.7 |
C4—C3—H3 | 118.9 | C12—C13—H13A | 109.5 |
C2—C3—H3 | 118.9 | C12—C13—H13B | 109.5 |
C3—C4—C5 | 119.52 (19) | H13A—C13—H13B | 109.5 |
C3—C4—H4 | 120.2 | C12—C13—H13C | 109.5 |
C5—C4—H4 | 120.2 | H13A—C13—H13C | 109.5 |
C6—C5—C4 | 120.55 (17) | H13B—C13—H13C | 109.5 |
C6—C5—N3 | 120.02 (19) | N4—C14—S1 | 178.61 (18) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O3ii | 0.85 (1) | 2.09 (1) | 2.931 (2) | 175 (3) |
O4—H4B···O1 | 0.85 (1) | 2.40 (1) | 3.227 (2) | 165 (3) |
O4—H4B···N4 | 0.85 (1) | 2.52 (2) | 2.992 (2) | 116 (2) |
N2—H2···O4 | 0.90 (1) | 2.01 (1) | 2.893 (2) | 167 (3) |
Symmetry code: (ii) −x, −y+1, −z. |