Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703108X/om2138sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703108X/om2138Isup2.hkl |
CCDC reference: 654843
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.008 Å
- R factor = 0.059
- wR factor = 0.189
- Data-to-parameter ratio = 18.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.98 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl4 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT432_ALERT_2_C Short Inter X...Y Contact O9 .. C16 .. 2.98 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A .. O4 .. 2.62 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 65.00 A 3
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 2.11 PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni2 (2) 2.06 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 18
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 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 3 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
All the reagents used were of commercial grade and used without further purification. N-Ethylethane-1,2-diamine (1.0 mmol, 88.2 mg) and pyridine-2-carbaldehyde (1.0 mmol, 107.1 mg) were mixed in a methanol solution (10 ml). The mixture was stirred for 1 h at room temperature. To the mixture was added with stirring a methanol solution (10 ml) of Ni(ClO4)2·7H2O (0.5 mmol, 192.0 mg). After keeping the filtrate in air for a week, green block-shaped crystals were formed.
H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances in the range 0.93–0.97 Å, N–H distances of 0.91 Å, and with Uiso(H) set at 1.2Ueq(C,N) and 1.5Ueq(methyl C). The structure contains solvent accessible voids of 65 Å3, which might accommodate a disordered methanol molecule.
The title complex is a mononuclear nickel(II) compound (Fig. 1). The structure consists of two mononuclear nickel(II) molecules, one with twofold symmetry, and four perchlorate anions, two with twofold symmetry. The Ni atom is six-coordinated by two Schiff base ligands. Each Schiff base ligand acts as a tridentate ligand, and ligates to the nickel atom through the imine N, amine N, and pyridine N atoms. The bond lengths related to the metal centres are comparable to the values in other similar nickel(II) complexes (Zhou et al., 2004; Li et al., 2005; Li et al., 2007).
For related literature, see: Li et al. (2005, 2007); Zhou et al. (2004).
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.
Fig. 1. The structure of compound (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
[Ni(C10H15N3)2](ClO4)2 | F(000) = 1908 |
Mr = 612.11 | Dx = 1.470 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 5221 reflections |
a = 21.1172 (18) Å | θ = 2.3–24.9° |
b = 16.8787 (14) Å | µ = 0.95 mm−1 |
c = 12.0819 (10) Å | T = 298 K |
β = 105.531 (1)° | Block, green |
V = 4149.1 (6) Å3 | 0.37 × 0.35 × 0.32 mm |
Z = 6 |
Bruker SMART CCD area-detector diffractometer | 9187 independent reflections |
Radiation source: fine-focus sealed tube | 5711 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −27→23 |
Tmin = 0.721, Tmax = 0.751 | k = −20→21 |
23631 measured reflections | l = −8→15 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.1156P)2] where P = (Fo2 + 2Fc2)/3 |
9187 reflections | (Δ/σ)max < 0.001 |
505 parameters | Δρmax = 1.86 e Å−3 |
18 restraints | Δρmin = −0.47 e Å−3 |
[Ni(C10H15N3)2](ClO4)2 | V = 4149.1 (6) Å3 |
Mr = 612.11 | Z = 6 |
Monoclinic, P2/c | Mo Kα radiation |
a = 21.1172 (18) Å | µ = 0.95 mm−1 |
b = 16.8787 (14) Å | T = 298 K |
c = 12.0819 (10) Å | 0.37 × 0.35 × 0.32 mm |
β = 105.531 (1)° |
Bruker SMART CCD area-detector diffractometer | 9187 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5711 reflections with I > 2σ(I) |
Tmin = 0.721, Tmax = 0.751 | Rint = 0.033 |
23631 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 18 restraints |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 0.99 | Δρmax = 1.86 e Å−3 |
9187 reflections | Δρmin = −0.47 e Å−3 |
505 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 | 0.31911 (2) | 0.27828 (3) | 0.42248 (4) | 0.04209 (16) | |
Ni2 | 0.0000 | 0.19438 (4) | 0.7500 | 0.04130 (19) | |
Cl1 | 0.20287 (5) | 0.59652 (6) | 0.53647 (9) | 0.0550 (3) | |
Cl2 | 0.30375 (6) | 0.93789 (9) | 0.53709 (11) | 0.0734 (3) | |
Cl3 | 0.5000 | 0.44214 (9) | 0.7500 | 0.0589 (4) | |
Cl4 | 1.0000 | 0.88866 (11) | 0.7500 | 0.0808 (5) | |
O1 | 0.1344 (2) | 0.5861 (3) | 0.4961 (4) | 0.0975 (13) | |
O2 | 0.2341 (3) | 0.5720 (3) | 0.4539 (4) | 0.1139 (15) | |
O3 | 0.2268 (2) | 0.5531 (3) | 0.6417 (3) | 0.0907 (12) | |
O4 | 0.2134 (2) | 0.6791 (2) | 0.5604 (4) | 0.1028 (14) | |
O5 | 0.2732 (3) | 0.8631 (3) | 0.5367 (4) | 0.1117 (15) | |
O6 | 0.3564 (3) | 0.9301 (4) | 0.4928 (6) | 0.139 (2) | |
O7 | 0.3176 (4) | 0.9736 (5) | 0.6419 (7) | 0.178 (3) | |
O8 | 0.2592 (3) | 0.9910 (4) | 0.4709 (7) | 0.165 (3) | |
O9 | 0.44959 (18) | 0.3930 (2) | 0.7721 (4) | 0.0946 (13) | |
O10 | 0.4710 (2) | 0.4896 (3) | 0.6554 (4) | 0.0968 (13) | |
O11 | 0.9805 (6) | 0.8420 (7) | 0.8234 (9) | 0.247 (4) | |
O12 | 0.9476 (4) | 0.9348 (5) | 0.6847 (8) | 0.202 (4) | |
N1 | 0.41192 (17) | 0.22489 (19) | 0.4957 (3) | 0.0490 (8) | |
N2 | 0.30283 (18) | 0.1667 (2) | 0.3666 (3) | 0.0523 (8) | |
N3 | 0.21667 (17) | 0.2880 (2) | 0.3311 (3) | 0.0538 (8) | |
H3A | 0.2157 | 0.3014 | 0.2577 | 0.065* | |
N4 | 0.30009 (16) | 0.26354 (19) | 0.5868 (3) | 0.0479 (7) | |
N5 | 0.33348 (16) | 0.38789 (17) | 0.4875 (3) | 0.0467 (7) | |
N6 | 0.35160 (17) | 0.3331 (2) | 0.2886 (3) | 0.0511 (8) | |
H6A | 0.3149 | 0.3499 | 0.2352 | 0.061* | |
N7 | −0.04676 (17) | 0.28965 (19) | 0.8184 (3) | 0.0489 (8) | |
N8 | 0.05468 (16) | 0.1998 (2) | 0.9136 (3) | 0.0485 (8) | |
N9 | 0.07312 (17) | 0.1091 (2) | 0.7407 (3) | 0.0560 (9) | |
H9C | 0.0571 | 0.0602 | 0.7501 | 0.067* | |
C1 | 0.4097 (2) | 0.1459 (3) | 0.4762 (4) | 0.0590 (11) | |
C2 | 0.4615 (3) | 0.0978 (3) | 0.5292 (6) | 0.0881 (17) | |
H2 | 0.4581 | 0.0432 | 0.5181 | 0.106* | |
C3 | 0.5184 (3) | 0.1296 (4) | 0.5984 (6) | 0.0884 (17) | |
H3 | 0.5544 | 0.0980 | 0.6328 | 0.106* | |
C4 | 0.5198 (3) | 0.2089 (3) | 0.6140 (5) | 0.0769 (14) | |
H4 | 0.5577 | 0.2327 | 0.6589 | 0.092* | |
C5 | 0.4661 (2) | 0.2545 (3) | 0.5646 (4) | 0.0585 (10) | |
H5 | 0.4679 | 0.3085 | 0.5802 | 0.070* | |
C6 | 0.3490 (3) | 0.1178 (3) | 0.3993 (4) | 0.0638 (12) | |
H6 | 0.3442 | 0.0653 | 0.3748 | 0.077* | |
C7 | 0.2369 (3) | 0.1508 (3) | 0.2934 (5) | 0.0712 (13) | |
H7A | 0.2243 | 0.0967 | 0.3042 | 0.085* | |
H7B | 0.2360 | 0.1577 | 0.2133 | 0.085* | |
C8 | 0.1907 (2) | 0.2069 (3) | 0.3253 (4) | 0.0679 (13) | |
H8A | 0.1483 | 0.2044 | 0.2688 | 0.081* | |
H8B | 0.1845 | 0.1921 | 0.3993 | 0.081* | |
C9 | 0.1764 (2) | 0.3482 (4) | 0.3703 (4) | 0.0725 (14) | |
H9A | 0.1997 | 0.3983 | 0.3798 | 0.087* | |
H9B | 0.1719 | 0.3325 | 0.4451 | 0.087* | |
C10 | 0.1076 (2) | 0.3609 (4) | 0.2898 (5) | 0.0830 (16) | |
H10A | 0.1111 | 0.3723 | 0.2138 | 0.125* | |
H10B | 0.0868 | 0.4045 | 0.3170 | 0.125* | |
H10C | 0.0819 | 0.3138 | 0.2881 | 0.125* | |
C11 | 0.30700 (18) | 0.3322 (2) | 0.6458 (3) | 0.0481 (9) | |
C12 | 0.2992 (2) | 0.3359 (3) | 0.7559 (4) | 0.0640 (12) | |
H12 | 0.3018 | 0.3843 | 0.7936 | 0.077* | |
C13 | 0.2877 (3) | 0.2682 (4) | 0.8086 (4) | 0.0748 (15) | |
H13 | 0.2828 | 0.2698 | 0.8828 | 0.090* | |
C14 | 0.2833 (2) | 0.1975 (3) | 0.7507 (4) | 0.0704 (13) | |
H14 | 0.2764 | 0.1504 | 0.7858 | 0.084* | |
C15 | 0.2892 (2) | 0.1974 (3) | 0.6397 (4) | 0.0559 (10) | |
H15 | 0.2855 | 0.1496 | 0.6003 | 0.067* | |
C16 | 0.3246 (2) | 0.3997 (2) | 0.5852 (4) | 0.0522 (10) | |
H16 | 0.3291 | 0.4501 | 0.6176 | 0.063* | |
C17 | 0.3510 (2) | 0.4467 (2) | 0.4132 (4) | 0.0590 (11) | |
H17A | 0.3785 | 0.4874 | 0.4588 | 0.071* | |
H17B | 0.3118 | 0.4716 | 0.3654 | 0.071* | |
C18 | 0.3879 (2) | 0.4048 (3) | 0.3391 (4) | 0.0601 (11) | |
H18A | 0.3928 | 0.4399 | 0.2784 | 0.072* | |
H18B | 0.4314 | 0.3902 | 0.3852 | 0.072* | |
C19 | 0.3889 (3) | 0.2821 (3) | 0.2270 (5) | 0.0704 (13) | |
H19A | 0.3634 | 0.2346 | 0.2013 | 0.084* | |
H19B | 0.4296 | 0.2659 | 0.2813 | 0.084* | |
C20 | 0.4055 (3) | 0.3198 (4) | 0.1240 (5) | 0.0900 (17) | |
H20A | 0.3679 | 0.3481 | 0.0791 | 0.135* | |
H20B | 0.4175 | 0.2793 | 0.0777 | 0.135* | |
H20C | 0.4416 | 0.3559 | 0.1501 | 0.135* | |
C21 | −0.0118 (2) | 0.3087 (3) | 0.9265 (3) | 0.0511 (9) | |
C22 | −0.0265 (3) | 0.3722 (3) | 0.9825 (5) | 0.0741 (14) | |
H22 | −0.0016 | 0.3839 | 1.0565 | 0.089* | |
C23 | −0.0789 (3) | 0.4198 (4) | 0.9291 (6) | 0.0844 (16) | |
H23 | −0.0898 | 0.4639 | 0.9664 | 0.101* | |
C24 | −0.1139 (3) | 0.4012 (3) | 0.8219 (5) | 0.0749 (14) | |
H24 | −0.1496 | 0.4321 | 0.7843 | 0.090* | |
C25 | −0.0962 (2) | 0.3357 (3) | 0.7682 (4) | 0.0604 (11) | |
H25 | −0.1203 | 0.3238 | 0.6937 | 0.073* | |
C26 | 0.0431 (2) | 0.2535 (3) | 0.9762 (3) | 0.0551 (10) | |
H26 | 0.0681 | 0.2587 | 1.0519 | 0.066* | |
C27 | 0.1063 (2) | 0.1424 (3) | 0.9449 (4) | 0.0666 (12) | |
H27A | 0.0902 | 0.0944 | 0.9723 | 0.080* | |
H27B | 0.1423 | 0.1630 | 1.0057 | 0.080* | |
C28 | 0.1292 (2) | 0.1247 (3) | 0.8407 (5) | 0.0752 (14) | |
H28A | 0.1541 | 0.1694 | 0.8243 | 0.090* | |
H28B | 0.1580 | 0.0789 | 0.8553 | 0.090* | |
C29 | 0.0924 (3) | 0.1083 (4) | 0.6315 (5) | 0.0818 (15) | |
H29A | 0.1110 | 0.1595 | 0.6214 | 0.098* | |
H29B | 0.0534 | 0.1009 | 0.5684 | 0.098* | |
C30 | 0.1424 (3) | 0.0436 (4) | 0.6256 (6) | 0.099 (2) | |
H30A | 0.1861 | 0.0643 | 0.6537 | 0.148* | |
H30B | 0.1355 | 0.0267 | 0.5474 | 0.148* | |
H30C | 0.1368 | −0.0006 | 0.6720 | 0.148* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0470 (3) | 0.0382 (3) | 0.0413 (3) | −0.00535 (19) | 0.0122 (2) | −0.00498 (18) |
Ni2 | 0.0396 (4) | 0.0423 (4) | 0.0393 (4) | 0.000 | 0.0057 (3) | 0.000 |
Cl1 | 0.0577 (6) | 0.0561 (6) | 0.0508 (6) | −0.0040 (4) | 0.0138 (4) | 0.0025 (4) |
Cl2 | 0.0608 (7) | 0.0933 (9) | 0.0646 (7) | −0.0078 (6) | 0.0145 (5) | 0.0098 (6) |
Cl3 | 0.0446 (7) | 0.0530 (8) | 0.0717 (10) | 0.000 | 0.0025 (6) | 0.000 |
Cl4 | 0.0786 (12) | 0.0614 (10) | 0.1100 (15) | 0.000 | 0.0386 (11) | 0.000 |
O1 | 0.069 (2) | 0.109 (3) | 0.103 (3) | −0.017 (2) | 0.004 (2) | 0.024 (2) |
O2 | 0.125 (4) | 0.137 (4) | 0.098 (3) | 0.015 (3) | 0.060 (3) | −0.013 (3) |
O3 | 0.092 (3) | 0.106 (3) | 0.067 (2) | 0.017 (2) | 0.0094 (19) | 0.024 (2) |
O4 | 0.124 (4) | 0.065 (2) | 0.115 (3) | −0.012 (2) | 0.025 (3) | −0.008 (2) |
O5 | 0.117 (4) | 0.105 (3) | 0.115 (4) | −0.020 (3) | 0.036 (3) | 0.025 (3) |
O6 | 0.109 (4) | 0.147 (5) | 0.185 (6) | −0.011 (4) | 0.081 (4) | −0.002 (4) |
O7 | 0.194 (6) | 0.183 (6) | 0.161 (5) | −0.028 (5) | 0.056 (5) | −0.063 (5) |
O8 | 0.091 (4) | 0.160 (6) | 0.225 (7) | −0.011 (4) | 0.009 (4) | 0.086 (5) |
O9 | 0.060 (2) | 0.092 (3) | 0.125 (3) | −0.0135 (19) | 0.013 (2) | 0.030 (2) |
O10 | 0.084 (3) | 0.101 (3) | 0.093 (3) | 0.012 (2) | 0.003 (2) | 0.031 (2) |
O11 | 0.267 (8) | 0.254 (8) | 0.222 (7) | −0.082 (7) | 0.068 (6) | 0.066 (6) |
O12 | 0.204 (6) | 0.178 (6) | 0.202 (7) | 0.069 (5) | 0.016 (5) | −0.012 (5) |
N1 | 0.0518 (19) | 0.0443 (18) | 0.0517 (19) | −0.0033 (14) | 0.0153 (15) | −0.0045 (14) |
N2 | 0.063 (2) | 0.0439 (18) | 0.0500 (19) | −0.0118 (16) | 0.0160 (16) | −0.0104 (15) |
N3 | 0.0504 (19) | 0.066 (2) | 0.0447 (18) | −0.0030 (16) | 0.0120 (15) | −0.0045 (15) |
N4 | 0.0466 (18) | 0.0494 (19) | 0.0480 (18) | −0.0039 (14) | 0.0129 (14) | −0.0027 (14) |
N5 | 0.0462 (18) | 0.0368 (16) | 0.053 (2) | −0.0003 (13) | 0.0055 (14) | −0.0031 (14) |
N6 | 0.0492 (18) | 0.0555 (19) | 0.0481 (18) | −0.0056 (15) | 0.0120 (14) | 0.0019 (15) |
N7 | 0.0494 (18) | 0.0518 (19) | 0.0448 (18) | 0.0034 (14) | 0.0116 (14) | 0.0036 (14) |
N8 | 0.0454 (18) | 0.0546 (19) | 0.0403 (17) | 0.0012 (14) | 0.0025 (13) | 0.0028 (14) |
N9 | 0.051 (2) | 0.0526 (19) | 0.064 (2) | 0.0048 (15) | 0.0147 (16) | −0.0063 (16) |
C1 | 0.067 (3) | 0.046 (2) | 0.070 (3) | 0.008 (2) | 0.029 (2) | −0.004 (2) |
C2 | 0.095 (4) | 0.062 (3) | 0.111 (5) | 0.022 (3) | 0.032 (4) | −0.008 (3) |
C3 | 0.074 (4) | 0.087 (4) | 0.100 (4) | 0.029 (3) | 0.016 (3) | 0.000 (3) |
C4 | 0.061 (3) | 0.085 (4) | 0.082 (4) | 0.004 (3) | 0.015 (3) | −0.005 (3) |
C5 | 0.058 (3) | 0.061 (3) | 0.058 (3) | 0.004 (2) | 0.017 (2) | −0.003 (2) |
C6 | 0.084 (3) | 0.038 (2) | 0.073 (3) | −0.005 (2) | 0.026 (2) | −0.014 (2) |
C7 | 0.077 (3) | 0.064 (3) | 0.070 (3) | −0.027 (2) | 0.015 (2) | −0.017 (2) |
C8 | 0.063 (3) | 0.079 (3) | 0.060 (3) | −0.024 (2) | 0.014 (2) | −0.011 (2) |
C9 | 0.055 (3) | 0.105 (4) | 0.055 (3) | 0.008 (3) | 0.009 (2) | −0.012 (3) |
C10 | 0.055 (3) | 0.115 (4) | 0.080 (4) | 0.011 (3) | 0.019 (2) | −0.003 (3) |
C11 | 0.0379 (19) | 0.059 (2) | 0.045 (2) | −0.0020 (16) | 0.0080 (15) | −0.0121 (18) |
C12 | 0.058 (3) | 0.085 (3) | 0.051 (2) | −0.012 (2) | 0.018 (2) | −0.023 (2) |
C13 | 0.069 (3) | 0.113 (4) | 0.046 (2) | −0.023 (3) | 0.022 (2) | −0.014 (3) |
C14 | 0.065 (3) | 0.088 (3) | 0.060 (3) | −0.017 (3) | 0.019 (2) | 0.015 (3) |
C15 | 0.060 (3) | 0.056 (2) | 0.055 (2) | −0.0085 (19) | 0.0208 (19) | −0.0024 (19) |
C16 | 0.055 (2) | 0.042 (2) | 0.054 (2) | 0.0034 (17) | 0.0044 (18) | −0.0133 (17) |
C17 | 0.074 (3) | 0.040 (2) | 0.059 (3) | −0.0061 (19) | 0.009 (2) | 0.0025 (18) |
C18 | 0.060 (3) | 0.055 (2) | 0.065 (3) | −0.009 (2) | 0.016 (2) | 0.013 (2) |
C19 | 0.080 (3) | 0.069 (3) | 0.070 (3) | −0.010 (2) | 0.035 (3) | −0.009 (2) |
C20 | 0.094 (4) | 0.117 (5) | 0.071 (3) | −0.004 (4) | 0.043 (3) | −0.005 (3) |
C21 | 0.055 (2) | 0.055 (2) | 0.045 (2) | −0.0008 (18) | 0.0146 (17) | −0.0033 (18) |
C22 | 0.073 (3) | 0.087 (4) | 0.063 (3) | 0.003 (3) | 0.019 (2) | −0.023 (3) |
C23 | 0.080 (4) | 0.073 (3) | 0.109 (5) | 0.017 (3) | 0.040 (3) | −0.014 (3) |
C24 | 0.075 (3) | 0.066 (3) | 0.085 (4) | 0.026 (2) | 0.024 (3) | 0.009 (3) |
C25 | 0.063 (3) | 0.061 (3) | 0.055 (2) | 0.018 (2) | 0.012 (2) | 0.008 (2) |
C26 | 0.054 (2) | 0.069 (3) | 0.039 (2) | 0.000 (2) | 0.0057 (17) | −0.0001 (19) |
C27 | 0.068 (3) | 0.069 (3) | 0.053 (3) | 0.019 (2) | −0.002 (2) | 0.007 (2) |
C28 | 0.049 (3) | 0.079 (3) | 0.090 (4) | 0.017 (2) | 0.006 (2) | 0.002 (3) |
C29 | 0.075 (4) | 0.082 (4) | 0.095 (4) | 0.003 (3) | 0.035 (3) | −0.008 (3) |
C30 | 0.089 (4) | 0.091 (4) | 0.125 (6) | 0.012 (3) | 0.044 (4) | −0.032 (4) |
Ni1—N2 | 1.999 (3) | C4—H4 | 0.9300 |
Ni1—N5 | 2.001 (3) | C5—H5 | 0.9300 |
Ni1—N1 | 2.123 (3) | C6—H6 | 0.9300 |
Ni1—N6 | 2.130 (3) | C7—C8 | 1.483 (7) |
Ni1—N4 | 2.143 (3) | C7—H7A | 0.9700 |
Ni1—N3 | 2.156 (3) | C7—H7B | 0.9700 |
Ni2—N8i | 2.007 (3) | C8—H8A | 0.9700 |
Ni2—N8 | 2.007 (3) | C8—H8B | 0.9700 |
Ni2—N9i | 2.136 (3) | C9—C10 | 1.531 (7) |
Ni2—N9 | 2.136 (3) | C9—H9A | 0.9700 |
Ni2—N7 | 2.164 (3) | C9—H9B | 0.9700 |
Ni2—N7i | 2.164 (3) | C10—H10A | 0.9600 |
Cl1—O2 | 1.398 (4) | C10—H10B | 0.9600 |
Cl1—O1 | 1.407 (4) | C10—H10C | 0.9600 |
Cl1—O4 | 1.429 (4) | C11—C12 | 1.385 (6) |
Cl1—O3 | 1.437 (4) | C11—C16 | 1.456 (6) |
Cl2—O7 | 1.361 (7) | C12—C13 | 1.361 (7) |
Cl2—O6 | 1.363 (5) | C12—H12 | 0.9300 |
Cl2—O8 | 1.388 (6) | C13—C14 | 1.374 (8) |
Cl2—O5 | 1.418 (5) | C13—H13 | 0.9300 |
Cl3—O10ii | 1.396 (4) | C14—C15 | 1.379 (7) |
Cl3—O10 | 1.396 (4) | C14—H14 | 0.9300 |
Cl3—O9ii | 1.430 (4) | C15—H15 | 0.9300 |
Cl3—O9 | 1.430 (4) | C16—H16 | 0.9300 |
Cl4—O11iii | 1.331 (9) | C17—C18 | 1.510 (7) |
Cl4—O11 | 1.331 (9) | C17—H17A | 0.9700 |
Cl4—O12iii | 1.409 (7) | C17—H17B | 0.9700 |
Cl4—O12 | 1.409 (7) | C18—H18A | 0.9700 |
N1—C5 | 1.320 (6) | C18—H18B | 0.9700 |
N1—C1 | 1.353 (5) | C19—C20 | 1.520 (8) |
N2—C6 | 1.257 (6) | C19—H19A | 0.9700 |
N2—C7 | 1.461 (6) | C19—H19B | 0.9700 |
N3—C8 | 1.469 (6) | C20—H20A | 0.9600 |
N3—C9 | 1.482 (6) | C20—H20B | 0.9600 |
N3—H3A | 0.9100 | C20—H20C | 0.9600 |
N4—C15 | 1.337 (6) | C21—C22 | 1.348 (7) |
N4—C11 | 1.348 (5) | C21—C26 | 1.482 (6) |
N5—C16 | 1.260 (5) | C22—C23 | 1.380 (8) |
N5—C17 | 1.452 (5) | C22—H22 | 0.9300 |
N6—C18 | 1.473 (5) | C23—C24 | 1.345 (8) |
N6—C19 | 1.493 (6) | C23—H23 | 0.9300 |
N6—H6A | 0.9100 | C24—C25 | 1.382 (7) |
N7—C25 | 1.313 (5) | C24—H24 | 0.9300 |
N7—C21 | 1.355 (5) | C25—H25 | 0.9300 |
N8—C26 | 1.245 (6) | C26—H26 | 0.9300 |
N8—C27 | 1.432 (5) | C27—C28 | 1.495 (8) |
N9—C28 | 1.472 (6) | C27—H27A | 0.9700 |
N9—C29 | 1.482 (7) | C27—H27B | 0.9700 |
N9—H9C | 0.9100 | C28—H28A | 0.9700 |
C1—C2 | 1.375 (7) | C28—H28B | 0.9700 |
C1—C6 | 1.448 (7) | C29—C30 | 1.533 (8) |
C2—C3 | 1.376 (9) | C29—H29A | 0.9700 |
C2—H2 | 0.9300 | C29—H29B | 0.9700 |
C3—C4 | 1.350 (8) | C30—H30A | 0.9600 |
C3—H3 | 0.9300 | C30—H30B | 0.9600 |
C4—C5 | 1.368 (7) | C30—H30C | 0.9600 |
N2—Ni1—N5 | 176.21 (14) | N2—C7—C8 | 108.2 (4) |
N2—Ni1—N1 | 78.29 (14) | N2—C7—H7A | 110.1 |
N5—Ni1—N1 | 101.70 (13) | C8—C7—H7A | 110.1 |
N2—Ni1—N6 | 102.37 (14) | N2—C7—H7B | 110.1 |
N5—Ni1—N6 | 81.42 (14) | C8—C7—H7B | 110.1 |
N1—Ni1—N6 | 92.98 (13) | H7A—C7—H7B | 108.4 |
N2—Ni1—N4 | 98.36 (13) | N3—C8—C7 | 110.1 (4) |
N5—Ni1—N4 | 77.86 (13) | N3—C8—H8A | 109.6 |
N1—Ni1—N4 | 86.88 (13) | C7—C8—H8A | 109.6 |
N6—Ni1—N4 | 158.80 (13) | N3—C8—H8B | 109.6 |
N2—Ni1—N3 | 80.81 (14) | C7—C8—H8B | 109.6 |
N5—Ni1—N3 | 99.02 (13) | H8A—C8—H8B | 108.1 |
N1—Ni1—N3 | 158.99 (13) | N3—C9—C10 | 114.9 (4) |
N6—Ni1—N3 | 93.51 (13) | N3—C9—H9A | 108.5 |
N4—Ni1—N3 | 94.12 (13) | C10—C9—H9A | 108.5 |
N8i—Ni2—N8 | 174.7 (2) | N3—C9—H9B | 108.5 |
N8i—Ni2—N9i | 81.35 (14) | C10—C9—H9B | 108.5 |
N8—Ni2—N9i | 102.27 (14) | H9A—C9—H9B | 107.5 |
N8i—Ni2—N9 | 102.27 (14) | C9—C10—H10A | 109.5 |
N8—Ni2—N9 | 81.35 (14) | C9—C10—H10B | 109.5 |
N9i—Ni2—N9 | 95.2 (2) | H10A—C10—H10B | 109.5 |
N8i—Ni2—N7 | 98.11 (13) | C9—C10—H10C | 109.5 |
N8—Ni2—N7 | 77.91 (13) | H10A—C10—H10C | 109.5 |
N9i—Ni2—N7 | 94.05 (14) | H10B—C10—H10C | 109.5 |
N9—Ni2—N7 | 158.65 (13) | N4—C11—C12 | 121.6 (4) |
N8i—Ni2—N7i | 77.91 (13) | N4—C11—C16 | 114.4 (4) |
N8—Ni2—N7i | 98.11 (13) | C12—C11—C16 | 124.0 (4) |
N9i—Ni2—N7i | 158.65 (13) | C13—C12—C11 | 119.5 (4) |
N9—Ni2—N7i | 94.05 (14) | C13—C12—H12 | 120.2 |
N7—Ni2—N7i | 83.98 (18) | C11—C12—H12 | 120.2 |
O2—Cl1—O1 | 110.6 (3) | C12—C13—C14 | 119.2 (4) |
O2—Cl1—O4 | 110.8 (3) | C12—C13—H13 | 120.4 |
O1—Cl1—O4 | 106.4 (3) | C14—C13—H13 | 120.4 |
O2—Cl1—O3 | 111.1 (3) | C13—C14—C15 | 119.0 (5) |
O1—Cl1—O3 | 109.1 (3) | C13—C14—H14 | 120.5 |
O4—Cl1—O3 | 108.6 (3) | C15—C14—H14 | 120.5 |
O7—Cl2—O6 | 114.4 (5) | N4—C15—C14 | 122.4 (4) |
O7—Cl2—O8 | 101.2 (5) | N4—C15—H15 | 118.8 |
O6—Cl2—O8 | 109.5 (5) | C14—C15—H15 | 118.8 |
O7—Cl2—O5 | 112.4 (4) | N5—C16—C11 | 118.0 (3) |
O6—Cl2—O5 | 109.4 (4) | N5—C16—H16 | 121.0 |
O8—Cl2—O5 | 109.6 (3) | C11—C16—H16 | 121.0 |
O10ii—Cl3—O10 | 110.0 (4) | N5—C17—C18 | 107.7 (3) |
O10ii—Cl3—O9ii | 107.5 (2) | N5—C17—H17A | 110.2 |
O10—Cl3—O9ii | 111.4 (3) | C18—C17—H17A | 110.2 |
O10ii—Cl3—O9 | 111.4 (3) | N5—C17—H17B | 110.2 |
O10—Cl3—O9 | 107.5 (2) | C18—C17—H17B | 110.2 |
O9ii—Cl3—O9 | 109.1 (4) | H17A—C17—H17B | 108.5 |
O11iii—Cl4—O11 | 107.4 (12) | N6—C18—C17 | 109.7 (4) |
O11iii—Cl4—O12iii | 111.3 (7) | N6—C18—H18A | 109.7 |
O11—Cl4—O12iii | 106.9 (6) | C17—C18—H18A | 109.7 |
O11iii—Cl4—O12 | 106.9 (6) | N6—C18—H18B | 109.7 |
O11—Cl4—O12 | 111.3 (7) | C17—C18—H18B | 109.7 |
O12iii—Cl4—O12 | 112.9 (8) | H18A—C18—H18B | 108.2 |
C5—N1—C1 | 117.8 (4) | N6—C19—C20 | 115.8 (5) |
C5—N1—Ni1 | 130.5 (3) | N6—C19—H19A | 108.3 |
C1—N1—Ni1 | 111.2 (3) | C20—C19—H19A | 108.3 |
C6—N2—C7 | 127.0 (4) | N6—C19—H19B | 108.3 |
C6—N2—Ni1 | 117.7 (3) | C20—C19—H19B | 108.3 |
C7—N2—Ni1 | 115.3 (3) | H19A—C19—H19B | 107.4 |
C8—N3—C9 | 114.5 (4) | C19—C20—H20A | 109.5 |
C8—N3—Ni1 | 105.3 (3) | C19—C20—H20B | 109.5 |
C9—N3—Ni1 | 118.2 (3) | H20A—C20—H20B | 109.5 |
C8—N3—H3A | 106.0 | C19—C20—H20C | 109.5 |
C9—N3—H3A | 106.0 | H20A—C20—H20C | 109.5 |
Ni1—N3—H3A | 106.0 | H20B—C20—H20C | 109.5 |
C15—N4—C11 | 118.2 (4) | C22—C21—N7 | 122.1 (4) |
C15—N4—Ni1 | 129.7 (3) | C22—C21—C26 | 123.9 (4) |
C11—N4—Ni1 | 111.7 (3) | N7—C21—C26 | 114.0 (4) |
C16—N5—C17 | 126.8 (3) | C21—C22—C23 | 119.6 (5) |
C16—N5—Ni1 | 118.0 (3) | C21—C22—H22 | 120.2 |
C17—N5—Ni1 | 115.2 (3) | C23—C22—H22 | 120.2 |
C18—N6—C19 | 113.3 (4) | C24—C23—C22 | 118.6 (5) |
C18—N6—Ni1 | 106.2 (3) | C24—C23—H23 | 120.7 |
C19—N6—Ni1 | 116.6 (3) | C22—C23—H23 | 120.7 |
C18—N6—H6A | 106.7 | C23—C24—C25 | 119.4 (5) |
C19—N6—H6A | 106.7 | C23—C24—H24 | 120.3 |
Ni1—N6—H6A | 106.7 | C25—C24—H24 | 120.3 |
C25—N7—C21 | 117.8 (4) | N7—C25—C24 | 122.5 (5) |
C25—N7—Ni2 | 130.7 (3) | N7—C25—H25 | 118.7 |
C21—N7—Ni2 | 110.9 (3) | C24—C25—H25 | 118.7 |
C26—N8—C27 | 126.3 (4) | N8—C26—C21 | 118.1 (4) |
C26—N8—Ni2 | 118.5 (3) | N8—C26—H26 | 121.0 |
C27—N8—Ni2 | 115.2 (3) | C21—C26—H26 | 121.0 |
C28—N9—C29 | 112.3 (4) | N8—C27—C28 | 107.9 (4) |
C28—N9—Ni2 | 105.7 (3) | N8—C27—H27A | 110.1 |
C29—N9—Ni2 | 115.3 (3) | C28—C27—H27A | 110.1 |
C28—N9—H9C | 107.8 | N8—C27—H27B | 110.1 |
C29—N9—H9C | 107.8 | C28—C27—H27B | 110.1 |
Ni2—N9—H9C | 107.8 | H27A—C27—H27B | 108.4 |
N1—C1—C2 | 121.0 (5) | N9—C28—C27 | 110.8 (4) |
N1—C1—C6 | 114.7 (4) | N9—C28—H28A | 109.5 |
C2—C1—C6 | 124.3 (4) | C27—C28—H28A | 109.5 |
C1—C2—C3 | 120.6 (5) | N9—C28—H28B | 109.5 |
C1—C2—H2 | 119.7 | C27—C28—H28B | 109.5 |
C3—C2—H2 | 119.7 | H28A—C28—H28B | 108.1 |
C4—C3—C2 | 117.0 (5) | N9—C29—C30 | 113.9 (5) |
C4—C3—H3 | 121.5 | N9—C29—H29A | 108.8 |
C2—C3—H3 | 121.5 | C30—C29—H29A | 108.8 |
C3—C4—C5 | 120.9 (5) | N9—C29—H29B | 108.8 |
C3—C4—H4 | 119.6 | C30—C29—H29B | 108.8 |
C5—C4—H4 | 119.6 | H29A—C29—H29B | 107.7 |
N1—C5—C4 | 122.6 (5) | C29—C30—H30A | 109.5 |
N1—C5—H5 | 118.7 | C29—C30—H30B | 109.5 |
C4—C5—H5 | 118.7 | H30A—C30—H30B | 109.5 |
N2—C6—C1 | 117.7 (4) | C29—C30—H30C | 109.5 |
N2—C6—H6 | 121.1 | H30A—C30—H30C | 109.5 |
C1—C6—H6 | 121.1 | H30B—C30—H30C | 109.5 |
Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1, y, −z+3/2; (iii) −x+2, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4iv | 0.91 | 2.39 | 3.300 (6) | 173 |
N6—H6A···O3iv | 0.91 | 2.51 | 3.359 (6) | 156 |
N6—H6A···O4iv | 0.91 | 2.62 | 3.443 (6) | 150 |
N9—H9C···O12v | 0.91 | 2.27 | 3.141 (9) | 160 |
Symmetry codes: (iv) x, −y+1, z−1/2; (v) −x+1, y−1, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C10H15N3)2](ClO4)2 |
Mr | 612.11 |
Crystal system, space group | Monoclinic, P2/c |
Temperature (K) | 298 |
a, b, c (Å) | 21.1172 (18), 16.8787 (14), 12.0819 (10) |
β (°) | 105.531 (1) |
V (Å3) | 4149.1 (6) |
Z | 6 |
Radiation type | Mo Kα |
µ (mm−1) | 0.95 |
Crystal size (mm) | 0.37 × 0.35 × 0.32 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.721, 0.751 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23631, 9187, 5711 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.189, 0.99 |
No. of reflections | 9187 |
No. of parameters | 505 |
No. of restraints | 18 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.86, −0.47 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4i | 0.91 | 2.39 | 3.300 (6) | 173 |
N6—H6A···O3i | 0.91 | 2.51 | 3.359 (6) | 156 |
N6—H6A···O4i | 0.91 | 2.62 | 3.443 (6) | 150 |
N9—H9C···O12ii | 0.91 | 2.27 | 3.141 (9) | 160 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1, y−1, −z+3/2. |
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The title complex is a mononuclear nickel(II) compound (Fig. 1). The structure consists of two mononuclear nickel(II) molecules, one with twofold symmetry, and four perchlorate anions, two with twofold symmetry. The Ni atom is six-coordinated by two Schiff base ligands. Each Schiff base ligand acts as a tridentate ligand, and ligates to the nickel atom through the imine N, amine N, and pyridine N atoms. The bond lengths related to the metal centres are comparable to the values in other similar nickel(II) complexes (Zhou et al., 2004; Li et al., 2005; Li et al., 2007).