



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810038298/hb5649sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810038298/hb5649Isup2.hkl |
CCDC reference: 799412
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.091
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 -- C27 .. 6.76 su PLAT230_ALERT_2_C Hirshfeld Test Diff for S2 -- C28 .. 5.36 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 -- C21 .. 5.37 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni2 -- N6 .. 7.15 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 12 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 30
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
3-Methoxysalicylaldehyde (152 mg, 1.0 mmol), N,N-dimethylpropane-1,3-diamine (102 mg, 1.0 mmol), ammonium thiocyanate (76 mg, 1.0 mmol), and nickel acetate tetrahydrate (249 mg, 1.0 mmol) were dissolved in methanol (80 ml). The mixture was stirred for two hours at room temperature. The resulting solution was left in air for a few days, yielding green blocks of (I).
H2 and H5A were located from a difference Fourier map and refined isotropically, with N–H distances restrained to 0.90 (1) Å. The remaining H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances of 0.93–0.97 Å, and with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(Cmethyl).
Recently, we have reported a few Schiff base complexes (Xue et al., 2010a,b). In this paper, a new nickel(II) complex with the Schiff base 2-[(3-dimethylammoniopropylimino)methyl]-6-methoxyphenol, is reported.
The complex is a centrosymmetric mononuclear nickel(II) complex, as shown in Fig. 1. The Ni atom, lying on the inversion center, is six-coordinated in an octahedral geometry, with two phenolate O and two imine N atoms from two Schiff base ligands defining the basal plane, and with two thiocyanate N atoms occupying the axial positions. The two amine N atoms are protonated, and form intramolecular N–H···O hydrogen bonds (Table 1) with the phenolate O atoms. The slight distortion of the octahedral coordination can be observed from the coordinate bond lengths and angles (Table 2).
For related structures and background references, see: Xue et al. (2010a,b).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Ni(NCS)2(C13H20N2O2)2] | F(000) = 1368 |
Mr = 647.49 | Dx = 1.376 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5211 reflections |
a = 16.228 (2) Å | θ = 2.6–27.2° |
b = 15.642 (2) Å | µ = 0.80 mm−1 |
c = 13.3912 (18) Å | T = 298 K |
β = 113.132 (2)° | Block, green |
V = 3126.0 (7) Å3 | 0.23 × 0.23 × 0.20 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 6772 independent reflections |
Radiation source: fine-focus sealed tube | 4916 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 27.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→20 |
Tmin = 0.838, Tmax = 0.857 | k = −19→19 |
17748 measured reflections | l = −17→7 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0418P)2 + 0.616P] where P = (Fo2 + 2Fc2)/3 |
6772 reflections | (Δ/σ)max = 0.001 |
385 parameters | Δρmax = 0.26 e Å−3 |
2 restraints | Δρmin = −0.38 e Å−3 |
[Ni(NCS)2(C13H20N2O2)2] | V = 3126.0 (7) Å3 |
Mr = 647.49 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.228 (2) Å | µ = 0.80 mm−1 |
b = 15.642 (2) Å | T = 298 K |
c = 13.3912 (18) Å | 0.23 × 0.23 × 0.20 mm |
β = 113.132 (2)° |
Bruker SMART CCD diffractometer | 6772 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4916 reflections with I > 2σ(I) |
Tmin = 0.838, Tmax = 0.857 | Rint = 0.026 |
17748 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 2 restraints |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.26 e Å−3 |
6772 reflections | Δρmin = −0.38 e Å−3 |
385 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 | ||
Ni1 | 0.5000 | 0.5000 | 0.0000 | 0.03134 (10) | |
Ni2 | 0.0000 | 0.5000 | 0.0000 | 0.03281 (10) | |
S1 | 0.28158 (5) | 0.31526 (5) | −0.26156 (5) | 0.0710 (2) | |
S2 | 0.18778 (4) | 0.75758 (4) | 0.05566 (5) | 0.05524 (17) | |
O1 | 0.48274 (9) | 0.43998 (8) | 0.12568 (11) | 0.0399 (3) | |
O2 | 0.54271 (11) | 0.39569 (10) | 0.33999 (13) | 0.0592 (4) | |
O3 | 0.01284 (9) | 0.51671 (8) | 0.15603 (11) | 0.0395 (3) | |
O4 | −0.02789 (11) | 0.52191 (10) | 0.33375 (13) | 0.0528 (4) | |
N1 | 0.38379 (10) | 0.57261 (10) | −0.02589 (13) | 0.0341 (4) | |
N2 | 0.50658 (12) | 0.73003 (11) | −0.11985 (15) | 0.0408 (4) | |
N3 | 0.41756 (12) | 0.41330 (11) | −0.11307 (15) | 0.0452 (4) | |
N4 | 0.11950 (10) | 0.42923 (10) | 0.05634 (13) | 0.0347 (4) | |
N5 | 0.00617 (11) | 0.31873 (10) | −0.21919 (14) | 0.0398 (4) | |
N6 | 0.08080 (12) | 0.61079 (11) | 0.00524 (15) | 0.0443 (4) | |
C1 | 0.37093 (12) | 0.53225 (12) | 0.14375 (15) | 0.0328 (4) | |
C2 | 0.44253 (13) | 0.47353 (12) | 0.18471 (16) | 0.0337 (4) | |
C3 | 0.46936 (14) | 0.44942 (13) | 0.29512 (17) | 0.0408 (5) | |
C4 | 0.42342 (15) | 0.47622 (14) | 0.35629 (17) | 0.0441 (5) | |
H4 | 0.4417 | 0.4577 | 0.4278 | 0.053* | |
C5 | 0.35069 (15) | 0.53011 (15) | 0.31371 (18) | 0.0456 (5) | |
H5 | 0.3195 | 0.5473 | 0.3556 | 0.055* | |
C6 | 0.32498 (13) | 0.55794 (13) | 0.20875 (17) | 0.0395 (5) | |
H6 | 0.2762 | 0.5946 | 0.1798 | 0.047* | |
C7 | 0.62574 (17) | 0.4410 (2) | 0.3822 (2) | 0.0724 (8) | |
H7A | 0.6307 | 0.4765 | 0.3264 | 0.109* | |
H7B | 0.6744 | 0.4009 | 0.4067 | 0.109* | |
H7C | 0.6279 | 0.4760 | 0.4421 | 0.109* | |
C8 | 0.34179 (13) | 0.57118 (12) | 0.03718 (16) | 0.0357 (4) | |
H8 | 0.2863 | 0.5982 | 0.0119 | 0.043* | |
C9 | 0.34050 (14) | 0.62316 (14) | −0.12656 (17) | 0.0428 (5) | |
H9A | 0.2767 | 0.6115 | −0.1568 | 0.051* | |
H9B | 0.3643 | 0.6052 | −0.1793 | 0.051* | |
C10 | 0.35530 (15) | 0.71901 (14) | −0.10719 (19) | 0.0491 (6) | |
H10A | 0.3274 | 0.7480 | −0.1764 | 0.059* | |
H10B | 0.3246 | 0.7375 | −0.0617 | 0.059* | |
C11 | 0.45174 (15) | 0.74753 (13) | −0.05485 (18) | 0.0472 (5) | |
H11A | 0.4529 | 0.8085 | −0.0412 | 0.057* | |
H11B | 0.4796 | 0.7192 | 0.0149 | 0.057* | |
C12 | 0.60227 (16) | 0.75222 (18) | −0.0561 (2) | 0.0653 (7) | |
H12A | 0.6366 | 0.7408 | −0.0990 | 0.098* | |
H12B | 0.6250 | 0.7184 | 0.0089 | 0.098* | |
H12C | 0.6069 | 0.8117 | −0.0373 | 0.098* | |
C13 | 0.47408 (16) | 0.77696 (15) | −0.22516 (18) | 0.0542 (6) | |
H13A | 0.4762 | 0.8374 | −0.2117 | 0.081* | |
H13B | 0.4135 | 0.7602 | −0.2683 | 0.081* | |
H13C | 0.5116 | 0.7635 | −0.2634 | 0.081* | |
C14 | 0.14218 (13) | 0.42832 (12) | 0.24865 (16) | 0.0359 (5) | |
C15 | 0.06605 (13) | 0.47581 (12) | 0.24231 (16) | 0.0361 (5) | |
C16 | 0.04936 (15) | 0.48005 (13) | 0.33849 (17) | 0.0424 (5) | |
C17 | 0.10847 (17) | 0.44819 (14) | 0.43617 (18) | 0.0512 (6) | |
H17 | 0.0965 | 0.4543 | 0.4983 | 0.061* | |
C18 | 0.18630 (16) | 0.40673 (14) | 0.44204 (18) | 0.0517 (6) | |
H18 | 0.2275 | 0.3867 | 0.5082 | 0.062* | |
C19 | 0.20132 (14) | 0.39593 (13) | 0.34964 (17) | 0.0453 (5) | |
H19 | 0.2521 | 0.3663 | 0.3533 | 0.054* | |
C20 | −0.10592 (18) | 0.46990 (19) | 0.2910 (2) | 0.0693 (8) | |
H20A | −0.1103 | 0.4453 | 0.2234 | 0.104* | |
H20B | −0.1580 | 0.5042 | 0.2790 | 0.104* | |
H20C | −0.1022 | 0.4251 | 0.3416 | 0.104* | |
C21 | 0.16576 (13) | 0.41259 (12) | 0.15670 (17) | 0.0376 (5) | |
H21 | 0.2213 | 0.3873 | 0.1723 | 0.045* | |
C22 | 0.16275 (13) | 0.40526 (13) | −0.01820 (17) | 0.0407 (5) | |
H22A | 0.2264 | 0.4171 | 0.0166 | 0.049* | |
H22B | 0.1383 | 0.4403 | −0.0831 | 0.049* | |
C23 | 0.14924 (14) | 0.31075 (14) | −0.05085 (18) | 0.0461 (5) | |
H23A | 0.1805 | 0.2991 | −0.0980 | 0.055* | |
H23B | 0.1772 | 0.2764 | 0.0141 | 0.055* | |
C24 | 0.05311 (14) | 0.28187 (13) | −0.10793 (17) | 0.0448 (5) | |
H24A | 0.0520 | 0.2200 | −0.1135 | 0.054* | |
H24B | 0.0203 | 0.2977 | −0.0639 | 0.054* | |
C25 | 0.04371 (16) | 0.28787 (17) | −0.2978 (2) | 0.0575 (6) | |
H25A | 0.0398 | 0.2267 | −0.3023 | 0.086* | |
H25B | 0.1053 | 0.3049 | −0.2736 | 0.086* | |
H25C | 0.0102 | 0.3121 | −0.3680 | 0.086* | |
C26 | −0.09173 (14) | 0.30137 (17) | −0.26210 (19) | 0.0568 (6) | |
H26A | −0.1017 | 0.2408 | −0.2647 | 0.085* | |
H26B | −0.1199 | 0.3248 | −0.3339 | 0.085* | |
H26C | −0.1168 | 0.3274 | −0.2154 | 0.085* | |
C27 | 0.36096 (14) | 0.37389 (13) | −0.17575 (16) | 0.0374 (5) | |
C28 | 0.12526 (14) | 0.67114 (13) | 0.02399 (16) | 0.0378 (5) | |
H2 | 0.5041 (18) | 0.6730 (7) | −0.132 (2) | 0.080* | |
H5A | 0.0166 (17) | 0.3749 (7) | −0.207 (2) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0356 (2) | 0.02943 (18) | 0.03020 (19) | −0.00061 (14) | 0.01426 (15) | −0.00052 (14) |
Ni2 | 0.03240 (19) | 0.03016 (18) | 0.02986 (19) | 0.00455 (14) | 0.00575 (15) | −0.00108 (14) |
S1 | 0.0568 (4) | 0.1032 (6) | 0.0513 (4) | −0.0330 (4) | 0.0194 (3) | −0.0272 (4) |
S2 | 0.0585 (4) | 0.0471 (3) | 0.0575 (4) | −0.0116 (3) | 0.0200 (3) | 0.0014 (3) |
O1 | 0.0518 (9) | 0.0349 (7) | 0.0406 (8) | 0.0074 (6) | 0.0264 (7) | 0.0048 (6) |
O2 | 0.0665 (11) | 0.0570 (10) | 0.0538 (10) | 0.0182 (9) | 0.0232 (9) | 0.0186 (8) |
O3 | 0.0434 (8) | 0.0371 (7) | 0.0321 (7) | 0.0099 (6) | 0.0084 (6) | −0.0007 (6) |
O4 | 0.0635 (11) | 0.0478 (9) | 0.0506 (10) | 0.0036 (8) | 0.0261 (8) | −0.0062 (7) |
N1 | 0.0351 (9) | 0.0340 (8) | 0.0331 (9) | −0.0007 (7) | 0.0133 (7) | 0.0008 (7) |
N2 | 0.0445 (10) | 0.0334 (9) | 0.0467 (10) | 0.0033 (8) | 0.0204 (9) | 0.0088 (8) |
N3 | 0.0477 (11) | 0.0399 (10) | 0.0444 (10) | −0.0053 (8) | 0.0141 (9) | −0.0058 (8) |
N4 | 0.0327 (9) | 0.0303 (8) | 0.0365 (9) | 0.0017 (7) | 0.0087 (7) | −0.0034 (7) |
N5 | 0.0380 (9) | 0.0345 (9) | 0.0427 (10) | 0.0024 (8) | 0.0113 (8) | −0.0082 (8) |
N6 | 0.0416 (10) | 0.0398 (10) | 0.0475 (11) | 0.0034 (8) | 0.0133 (9) | −0.0019 (8) |
C1 | 0.0340 (10) | 0.0334 (9) | 0.0331 (10) | −0.0070 (8) | 0.0153 (9) | −0.0046 (8) |
C2 | 0.0366 (11) | 0.0312 (9) | 0.0362 (11) | −0.0070 (8) | 0.0174 (9) | −0.0030 (8) |
C3 | 0.0460 (12) | 0.0382 (11) | 0.0384 (12) | −0.0023 (9) | 0.0168 (10) | 0.0028 (9) |
C4 | 0.0545 (14) | 0.0480 (12) | 0.0317 (11) | −0.0076 (11) | 0.0189 (10) | 0.0008 (9) |
C5 | 0.0523 (14) | 0.0513 (12) | 0.0427 (13) | −0.0087 (11) | 0.0288 (11) | −0.0066 (11) |
C6 | 0.0360 (11) | 0.0429 (11) | 0.0424 (12) | −0.0048 (9) | 0.0184 (10) | −0.0035 (10) |
C7 | 0.0526 (16) | 0.108 (2) | 0.0479 (15) | 0.0185 (16) | 0.0110 (13) | −0.0012 (15) |
C8 | 0.0307 (10) | 0.0389 (11) | 0.0377 (11) | 0.0003 (8) | 0.0136 (9) | −0.0002 (9) |
C9 | 0.0349 (11) | 0.0547 (13) | 0.0362 (11) | 0.0008 (10) | 0.0110 (9) | 0.0086 (10) |
C10 | 0.0525 (14) | 0.0508 (13) | 0.0524 (14) | 0.0144 (11) | 0.0296 (11) | 0.0155 (11) |
C11 | 0.0639 (15) | 0.0369 (11) | 0.0480 (13) | 0.0042 (10) | 0.0297 (12) | 0.0034 (10) |
C12 | 0.0496 (14) | 0.0718 (17) | 0.0665 (17) | −0.0102 (13) | 0.0141 (13) | 0.0197 (14) |
C13 | 0.0613 (15) | 0.0538 (14) | 0.0496 (14) | 0.0080 (12) | 0.0240 (12) | 0.0166 (11) |
C14 | 0.0361 (11) | 0.0297 (10) | 0.0343 (11) | −0.0036 (8) | 0.0056 (9) | 0.0014 (8) |
C15 | 0.0415 (11) | 0.0263 (9) | 0.0331 (11) | −0.0025 (8) | 0.0068 (9) | −0.0021 (8) |
C16 | 0.0512 (13) | 0.0325 (10) | 0.0416 (12) | −0.0030 (9) | 0.0162 (11) | −0.0034 (9) |
C17 | 0.0718 (16) | 0.0454 (13) | 0.0335 (12) | −0.0090 (12) | 0.0176 (12) | −0.0002 (10) |
C18 | 0.0560 (14) | 0.0461 (13) | 0.0386 (13) | −0.0057 (11) | 0.0028 (11) | 0.0095 (10) |
C19 | 0.0406 (12) | 0.0386 (11) | 0.0443 (13) | −0.0019 (9) | 0.0035 (10) | 0.0066 (10) |
C20 | 0.0624 (17) | 0.0702 (17) | 0.086 (2) | −0.0055 (14) | 0.0402 (16) | −0.0064 (16) |
C21 | 0.0303 (10) | 0.0284 (9) | 0.0460 (12) | 0.0010 (8) | 0.0064 (9) | 0.0015 (9) |
C22 | 0.0343 (11) | 0.0443 (12) | 0.0393 (11) | 0.0029 (9) | 0.0098 (9) | −0.0033 (9) |
C23 | 0.0415 (12) | 0.0449 (12) | 0.0443 (12) | 0.0087 (10) | 0.0086 (10) | −0.0061 (10) |
C24 | 0.0496 (13) | 0.0352 (11) | 0.0458 (12) | 0.0050 (10) | 0.0145 (10) | −0.0024 (9) |
C25 | 0.0553 (15) | 0.0642 (16) | 0.0575 (15) | 0.0057 (12) | 0.0269 (12) | −0.0116 (13) |
C26 | 0.0411 (12) | 0.0712 (16) | 0.0525 (14) | −0.0069 (12) | 0.0123 (11) | −0.0120 (13) |
C27 | 0.0397 (11) | 0.0398 (11) | 0.0367 (11) | 0.0031 (9) | 0.0194 (10) | 0.0008 (9) |
C28 | 0.0386 (11) | 0.0380 (11) | 0.0357 (11) | 0.0089 (9) | 0.0134 (9) | 0.0035 (9) |
Ni1—O1 | 2.0403 (13) | C7—H7B | 0.9600 |
Ni1—O1i | 2.0403 (13) | C7—H7C | 0.9600 |
Ni1—N3i | 2.0809 (18) | C8—H8 | 0.9300 |
Ni1—N3 | 2.0809 (18) | C9—C10 | 1.524 (3) |
Ni1—N1 | 2.1102 (16) | C9—H9A | 0.9700 |
Ni1—N1i | 2.1102 (16) | C9—H9B | 0.9700 |
Ni2—O3ii | 2.0336 (14) | C10—C11 | 1.509 (3) |
Ni2—O3 | 2.0336 (14) | C10—H10A | 0.9700 |
Ni2—N4 | 2.0990 (15) | C10—H10B | 0.9700 |
Ni2—N4ii | 2.0990 (15) | C11—H11A | 0.9700 |
Ni2—N6 | 2.1577 (19) | C11—H11B | 0.9700 |
Ni2—N6ii | 2.1577 (19) | C12—H12A | 0.9600 |
S1—C27 | 1.630 (2) | C12—H12B | 0.9600 |
S2—C28 | 1.643 (2) | C12—H12C | 0.9600 |
O1—C2 | 1.316 (2) | C13—H13A | 0.9600 |
O2—C3 | 1.386 (3) | C13—H13B | 0.9600 |
O2—C7 | 1.428 (3) | C13—H13C | 0.9600 |
O3—C15 | 1.306 (2) | C14—C19 | 1.410 (3) |
O4—C16 | 1.394 (3) | C14—C15 | 1.415 (3) |
O4—C20 | 1.422 (3) | C14—C21 | 1.447 (3) |
N1—C8 | 1.277 (2) | C15—C16 | 1.418 (3) |
N1—C9 | 1.481 (2) | C16—C17 | 1.376 (3) |
N2—C12 | 1.489 (3) | C17—C18 | 1.394 (3) |
N2—C13 | 1.490 (3) | C17—H17 | 0.9300 |
N2—C11 | 1.494 (3) | C18—C19 | 1.362 (3) |
N2—H2 | 0.906 (10) | C18—H18 | 0.9300 |
N3—C27 | 1.150 (2) | C19—H19 | 0.9300 |
N4—C21 | 1.283 (2) | C20—H20A | 0.9600 |
N4—C22 | 1.477 (3) | C20—H20B | 0.9600 |
N5—C26 | 1.487 (3) | C20—H20C | 0.9600 |
N5—C25 | 1.488 (3) | C21—H21 | 0.9300 |
N5—C24 | 1.497 (3) | C22—C23 | 1.533 (3) |
N5—H5A | 0.897 (10) | C22—H22A | 0.9700 |
N6—C28 | 1.154 (3) | C22—H22B | 0.9700 |
C1—C6 | 1.409 (3) | C23—C24 | 1.512 (3) |
C1—C2 | 1.412 (3) | C23—H23A | 0.9700 |
C1—C8 | 1.450 (3) | C23—H23B | 0.9700 |
C2—C3 | 1.418 (3) | C24—H24A | 0.9700 |
C3—C4 | 1.372 (3) | C24—H24B | 0.9700 |
C4—C5 | 1.378 (3) | C25—H25A | 0.9600 |
C4—H4 | 0.9300 | C25—H25B | 0.9600 |
C5—C6 | 1.371 (3) | C25—H25C | 0.9600 |
C5—H5 | 0.9300 | C26—H26A | 0.9600 |
C6—H6 | 0.9300 | C26—H26B | 0.9600 |
C7—H7A | 0.9600 | C26—H26C | 0.9600 |
O1—Ni1—O1i | 180.00 (7) | C10—C9—H9B | 109.1 |
O1—Ni1—N3i | 87.54 (6) | H9A—C9—H9B | 107.8 |
O1i—Ni1—N3i | 92.46 (6) | C11—C10—C9 | 115.79 (18) |
O1—Ni1—N3 | 92.46 (6) | C11—C10—H10A | 108.3 |
O1i—Ni1—N3 | 87.54 (6) | C9—C10—H10A | 108.3 |
N3i—Ni1—N3 | 180.00 (7) | C11—C10—H10B | 108.3 |
O1—Ni1—N1 | 88.84 (6) | C9—C10—H10B | 108.3 |
O1i—Ni1—N1 | 91.16 (6) | H10A—C10—H10B | 107.4 |
N3i—Ni1—N1 | 92.66 (6) | N2—C11—C10 | 114.93 (18) |
N3—Ni1—N1 | 87.34 (6) | N2—C11—H11A | 108.5 |
O1—Ni1—N1i | 91.16 (6) | C10—C11—H11A | 108.5 |
O1i—Ni1—N1i | 88.84 (6) | N2—C11—H11B | 108.5 |
N3i—Ni1—N1i | 87.34 (6) | C10—C11—H11B | 108.5 |
N3—Ni1—N1i | 92.66 (6) | H11A—C11—H11B | 107.5 |
N1—Ni1—N1i | 180.00 (7) | N2—C12—H12A | 109.5 |
O3ii—Ni2—O3 | 180.000 (13) | N2—C12—H12B | 109.5 |
O3ii—Ni2—N4 | 90.50 (6) | H12A—C12—H12B | 109.5 |
O3—Ni2—N4 | 89.50 (6) | N2—C12—H12C | 109.5 |
O3ii—Ni2—N4ii | 89.50 (6) | H12A—C12—H12C | 109.5 |
O3—Ni2—N4ii | 90.50 (6) | H12B—C12—H12C | 109.5 |
N4—Ni2—N4ii | 180.0 | N2—C13—H13A | 109.5 |
O3ii—Ni2—N6 | 87.27 (6) | N2—C13—H13B | 109.5 |
O3—Ni2—N6 | 92.73 (6) | H13A—C13—H13B | 109.5 |
N4—Ni2—N6 | 87.02 (6) | N2—C13—H13C | 109.5 |
N4ii—Ni2—N6 | 92.98 (6) | H13A—C13—H13C | 109.5 |
O3ii—Ni2—N6ii | 92.73 (6) | H13B—C13—H13C | 109.5 |
O3—Ni2—N6ii | 87.27 (6) | C19—C14—C15 | 119.7 (2) |
N4—Ni2—N6ii | 92.98 (6) | C19—C14—C21 | 116.57 (19) |
N4ii—Ni2—N6ii | 87.02 (6) | C15—C14—C21 | 123.70 (17) |
N6—Ni2—N6ii | 180.0 | O3—C15—C14 | 124.64 (19) |
C2—O1—Ni1 | 124.97 (12) | O3—C15—C16 | 118.99 (19) |
C3—O2—C7 | 112.77 (19) | C14—C15—C16 | 116.35 (18) |
C15—O3—Ni2 | 127.67 (13) | C17—C16—O4 | 119.5 (2) |
C16—O4—C20 | 113.10 (18) | C17—C16—C15 | 122.4 (2) |
C8—N1—C9 | 115.21 (16) | O4—C16—C15 | 118.04 (19) |
C8—N1—Ni1 | 123.83 (13) | C16—C17—C18 | 120.0 (2) |
C9—N1—Ni1 | 120.71 (13) | C16—C17—H17 | 120.0 |
C12—N2—C13 | 109.21 (17) | C18—C17—H17 | 120.0 |
C12—N2—C11 | 110.42 (18) | C19—C18—C17 | 119.2 (2) |
C13—N2—C11 | 112.99 (17) | C19—C18—H18 | 120.4 |
C12—N2—H2 | 107.2 (17) | C17—C18—H18 | 120.4 |
C13—N2—H2 | 109.6 (18) | C18—C19—C14 | 122.0 (2) |
C11—N2—H2 | 107.2 (17) | C18—C19—H19 | 119.0 |
C27—N3—Ni1 | 168.91 (17) | C14—C19—H19 | 119.0 |
C21—N4—C22 | 114.76 (16) | O4—C20—H20A | 109.5 |
C21—N4—Ni2 | 124.16 (14) | O4—C20—H20B | 109.5 |
C22—N4—Ni2 | 120.55 (12) | H20A—C20—H20B | 109.5 |
C26—N5—C25 | 109.85 (17) | O4—C20—H20C | 109.5 |
C26—N5—C24 | 111.28 (18) | H20A—C20—H20C | 109.5 |
C25—N5—C24 | 112.90 (17) | H20B—C20—H20C | 109.5 |
C26—N5—H5A | 110.2 (17) | N4—C21—C14 | 127.99 (18) |
C25—N5—H5A | 110.1 (18) | N4—C21—H21 | 116.0 |
C24—N5—H5A | 102.3 (18) | C14—C21—H21 | 116.0 |
C28—N6—Ni2 | 169.71 (18) | N4—C22—C23 | 112.64 (17) |
C6—C1—C2 | 120.01 (18) | N4—C22—H22A | 109.1 |
C6—C1—C8 | 116.18 (18) | C23—C22—H22A | 109.1 |
C2—C1—C8 | 123.79 (18) | N4—C22—H22B | 109.1 |
O1—C2—C1 | 123.56 (18) | C23—C22—H22B | 109.1 |
O1—C2—C3 | 119.90 (18) | H22A—C22—H22B | 107.8 |
C1—C2—C3 | 116.52 (18) | C24—C23—C22 | 115.85 (17) |
C4—C3—O2 | 120.12 (19) | C24—C23—H23A | 108.3 |
C4—C3—C2 | 121.65 (19) | C22—C23—H23A | 108.3 |
O2—C3—C2 | 118.21 (19) | C24—C23—H23B | 108.3 |
C3—C4—C5 | 121.2 (2) | C22—C23—H23B | 108.3 |
C3—C4—H4 | 119.4 | H23A—C23—H23B | 107.4 |
C5—C4—H4 | 119.4 | N5—C24—C23 | 114.12 (18) |
C6—C5—C4 | 119.0 (2) | N5—C24—H24A | 108.7 |
C6—C5—H5 | 120.5 | C23—C24—H24A | 108.7 |
C4—C5—H5 | 120.5 | N5—C24—H24B | 108.7 |
C5—C6—C1 | 121.4 (2) | C23—C24—H24B | 108.7 |
C5—C6—H6 | 119.3 | H24A—C24—H24B | 107.6 |
C1—C6—H6 | 119.3 | N5—C25—H25A | 109.5 |
O2—C7—H7A | 109.5 | N5—C25—H25B | 109.5 |
O2—C7—H7B | 109.5 | H25A—C25—H25B | 109.5 |
H7A—C7—H7B | 109.5 | N5—C25—H25C | 109.5 |
O2—C7—H7C | 109.5 | H25A—C25—H25C | 109.5 |
H7A—C7—H7C | 109.5 | H25B—C25—H25C | 109.5 |
H7B—C7—H7C | 109.5 | N5—C26—H26A | 109.5 |
N1—C8—C1 | 127.30 (18) | N5—C26—H26B | 109.5 |
N1—C8—H8 | 116.3 | H26A—C26—H26B | 109.5 |
C1—C8—H8 | 116.3 | N5—C26—H26C | 109.5 |
N1—C9—C10 | 112.56 (17) | H26A—C26—H26C | 109.5 |
N1—C9—H9A | 109.1 | H26B—C26—H26C | 109.5 |
C10—C9—H9A | 109.1 | N3—C27—S1 | 178.0 (2) |
N1—C9—H9B | 109.1 | N6—C28—S2 | 177.5 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.91 (1) | 1.78 (1) | 2.668 (2) | 167 (3) |
N5—H5A···O3ii | 0.90 (1) | 1.96 (2) | 2.764 (2) | 149 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(NCS)2(C13H20N2O2)2] |
Mr | 647.49 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 16.228 (2), 15.642 (2), 13.3912 (18) |
β (°) | 113.132 (2) |
V (Å3) | 3126.0 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.80 |
Crystal size (mm) | 0.23 × 0.23 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.838, 0.857 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17748, 6772, 4916 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.091, 1.02 |
No. of reflections | 6772 |
No. of parameters | 385 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.38 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Ni1—O1 | 2.0403 (13) | Ni2—O3 | 2.0336 (14) |
Ni1—N3 | 2.0809 (18) | Ni2—N4 | 2.0990 (15) |
Ni1—N1 | 2.1102 (16) | Ni2—N6 | 2.1577 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.906 (10) | 1.778 (12) | 2.668 (2) | 167 (3) |
N5—H5A···O3ii | 0.897 (10) | 1.957 (16) | 2.764 (2) | 149 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z. |
Recently, we have reported a few Schiff base complexes (Xue et al., 2010a,b). In this paper, a new nickel(II) complex with the Schiff base 2-[(3-dimethylammoniopropylimino)methyl]-6-methoxyphenol, is reported.
The complex is a centrosymmetric mononuclear nickel(II) complex, as shown in Fig. 1. The Ni atom, lying on the inversion center, is six-coordinated in an octahedral geometry, with two phenolate O and two imine N atoms from two Schiff base ligands defining the basal plane, and with two thiocyanate N atoms occupying the axial positions. The two amine N atoms are protonated, and form intramolecular N–H···O hydrogen bonds (Table 1) with the phenolate O atoms. The slight distortion of the octahedral coordination can be observed from the coordinate bond lengths and angles (Table 2).