The title compound, [Ni(C14H18N4O2)2](NO3)2, the coordination environment of the metal centre is a slightly distorted octahedral, with the Ni atom linked to six N atoms. The Ni atom lies on a centre of symmetry.
Supporting information
CCDC reference: 627363
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.005 Å
- R factor = 0.050
- wR factor = 0.142
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.52
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.45
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C11
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C13
PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C10 .. 3.01 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O5 .. C9 .. 2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. O4 .. 2.75 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. N5 .. 2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. N5 .. 2.72 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 35.00 A 3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 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
5 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
6 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Bruker Nonius, 2004); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick 2003).
Bis[3,3-di-{
N-(propan-2-imine)oxy}-3
H-isoindol-1-amine-
κ2N,
N']nickel(II) dinitrate
top
Crystal data top
[Ni(C14H18N4O2)2](NO3)2 | F(000) = 764 |
Mr = 731.38 | Dx = 1.392 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 10960 reflections |
a = 10.8430 (16) Å | θ = 3.0–25.0° |
b = 9.4644 (8) Å | µ = 0.62 mm−1 |
c = 17.101 (2) Å | T = 120 K |
β = 96.101 (12)° | Block, purple |
V = 1745.0 (4) Å3 | 0.53 × 0.25 × 0.12 mm |
Z = 2 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2968 independent reflections |
Radiation source: fine-focus sealed tube | 2498 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.044 |
Detector resolution: 9 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
φ scans, and ω scans with κ offsets | h = −11→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.734, Tmax = 0.929 | l = −18→20 |
10960 measured reflections | |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0599P)2 + 3.615P] where P = (Fo2 + 2Fc2)/3 |
2968 reflections | (Δ/σ)max < 0.001 |
231 parameters | Δρmax = 1.25 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
Special details top
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 | Occ. (<1) |
Ni1 | 1.0000 | 0.0000 | 0.5000 | 0.0232 (2) | |
O1 | 0.9633 (2) | 0.1044 (2) | 0.33722 (12) | 0.0283 (5) | |
O2 | 0.9495 (2) | 0.2818 (2) | 0.42912 (13) | 0.0274 (5) | |
O3 | 0.5694 (3) | 0.1683 (3) | 0.30273 (16) | 0.0487 (7) | |
O4 | 0.5813 (3) | 0.1929 (3) | 0.42913 (17) | 0.0475 (7) | |
O5 | 0.6209 (3) | −0.0079 (3) | 0.37645 (18) | 0.0566 (9) | |
N1 | 1.1198 (3) | 0.1244 (3) | 0.44381 (15) | 0.0262 (6) | |
N2 | 0.9306 (3) | −0.0195 (3) | 0.37964 (16) | 0.0257 (6) | |
N3 | 0.9066 (3) | 0.1996 (3) | 0.49150 (15) | 0.0264 (6) | |
N4 | 1.3362 (3) | 0.1228 (3) | 0.47333 (18) | 0.0333 (7) | |
N5 | 0.5916 (3) | 0.1203 (3) | 0.36911 (18) | 0.0341 (7) | |
C1 | 1.0314 (3) | 0.1985 (3) | 0.38854 (18) | 0.0248 (7) | |
C2 | 1.1069 (3) | 0.2959 (3) | 0.34261 (18) | 0.0261 (7) | |
C3 | 1.0715 (4) | 0.3943 (4) | 0.28470 (19) | 0.0305 (8) | |
H3 | 0.9870 | 0.4087 | 0.2655 | 0.037* | |
C4 | 1.1669 (4) | 0.4713 (4) | 0.2560 (2) | 0.0334 (8) | |
H4 | 1.1464 | 0.5405 | 0.2165 | 0.040* | |
C5 | 1.2910 (4) | 0.4500 (4) | 0.2832 (2) | 0.0328 (8) | |
H5 | 1.3532 | 0.5039 | 0.2617 | 0.039* | |
C6 | 1.3253 (3) | 0.3510 (4) | 0.34144 (19) | 0.0293 (7) | |
H6 | 1.4098 | 0.3364 | 0.3607 | 0.035* | |
C7 | 1.2307 (3) | 0.2744 (3) | 0.37029 (18) | 0.0261 (7) | |
C8 | 1.2325 (3) | 0.1670 (3) | 0.43367 (18) | 0.0265 (7) | |
C9 | 0.8622 (3) | −0.1017 (4) | 0.33486 (19) | 0.0269 (7) | |
C10 | 0.8166 (3) | −0.0649 (4) | 0.2522 (2) | 0.0340 (8) | |
H10A | 0.8467 | 0.0293 | 0.2398 | 0.051* | 0.50 |
H10B | 0.7257 | −0.0652 | 0.2459 | 0.051* | 0.50 |
H10C | 0.8472 | −0.1345 | 0.2165 | 0.051* | 0.50 |
H10D | 0.7664 | −0.1428 | 0.2283 | 0.051* | 0.50 |
H10E | 0.8874 | −0.0484 | 0.2222 | 0.051* | 0.50 |
H10F | 0.7659 | 0.0209 | 0.2516 | 0.051* | 0.50 |
C11 | 0.8281 (3) | −0.2410 (4) | 0.3672 (2) | 0.0315 (8) | |
H11A | 0.8650 | −0.2494 | 0.4219 | 0.047* | |
H11B | 0.8593 | −0.3172 | 0.3358 | 0.047* | |
H11C | 0.7377 | −0.2480 | 0.3651 | 0.047* | |
C12 | 0.8290 (3) | 0.2712 (3) | 0.52722 (19) | 0.0286 (7) | |
C13 | 0.7792 (4) | 0.2061 (4) | 0.5964 (2) | 0.0366 (9) | |
H13A | 0.8130 | 0.1106 | 0.6045 | 0.055* | |
H13B | 0.6885 | 0.2013 | 0.5871 | 0.055* | |
H13C | 0.8032 | 0.2636 | 0.6432 | 0.055* | |
C14 | 0.7895 (4) | 0.4177 (4) | 0.5036 (2) | 0.0374 (9) | |
H14A | 0.8297 | 0.4461 | 0.4574 | 0.056* | 0.50 |
H14B | 0.8137 | 0.4829 | 0.5471 | 0.056* | 0.50 |
H14C | 0.6993 | 0.4203 | 0.4909 | 0.056* | 0.50 |
H14D | 0.7321 | 0.4534 | 0.5395 | 0.056* | 0.50 |
H14E | 0.7481 | 0.4166 | 0.4498 | 0.056* | 0.50 |
H14F | 0.8625 | 0.4792 | 0.5060 | 0.056* | 0.50 |
H4B | 1.334 (4) | 0.065 (5) | 0.514 (2) | 0.035 (10)* | |
H4A | 1.409 (5) | 0.168 (6) | 0.463 (3) | 0.064 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0372 (4) | 0.0131 (3) | 0.0209 (3) | 0.0007 (2) | 0.0100 (2) | 0.0016 (2) |
O1 | 0.0453 (14) | 0.0158 (11) | 0.0247 (11) | −0.0035 (10) | 0.0085 (10) | 0.0055 (9) |
O2 | 0.0432 (14) | 0.0141 (11) | 0.0274 (11) | 0.0036 (10) | 0.0148 (10) | 0.0062 (9) |
O3 | 0.0629 (19) | 0.0394 (17) | 0.0440 (16) | 0.0039 (14) | 0.0077 (13) | 0.0123 (13) |
O4 | 0.0450 (16) | 0.0480 (18) | 0.0486 (16) | −0.0037 (13) | 0.0004 (13) | −0.0141 (14) |
O5 | 0.079 (2) | 0.049 (2) | 0.0423 (16) | 0.0254 (16) | 0.0112 (15) | 0.0092 (14) |
N1 | 0.0420 (17) | 0.0148 (14) | 0.0227 (13) | 0.0033 (12) | 0.0084 (12) | 0.0023 (10) |
N2 | 0.0368 (16) | 0.0144 (13) | 0.0275 (14) | −0.0005 (11) | 0.0113 (12) | 0.0032 (11) |
N3 | 0.0408 (16) | 0.0159 (14) | 0.0239 (13) | −0.0025 (12) | 0.0110 (12) | 0.0030 (11) |
N4 | 0.0399 (19) | 0.0306 (17) | 0.0301 (15) | 0.0036 (14) | 0.0075 (13) | 0.0042 (13) |
N5 | 0.0326 (16) | 0.0327 (18) | 0.0390 (17) | −0.0007 (13) | 0.0135 (13) | 0.0043 (14) |
C1 | 0.0344 (18) | 0.0158 (16) | 0.0254 (15) | −0.0005 (13) | 0.0090 (13) | 0.0021 (12) |
C2 | 0.044 (2) | 0.0138 (16) | 0.0227 (14) | 0.0021 (14) | 0.0129 (14) | −0.0013 (12) |
C3 | 0.046 (2) | 0.0188 (17) | 0.0280 (16) | 0.0016 (15) | 0.0113 (15) | 0.0024 (13) |
C4 | 0.054 (2) | 0.0211 (18) | 0.0272 (17) | 0.0011 (15) | 0.0156 (16) | 0.0053 (13) |
C5 | 0.049 (2) | 0.0209 (18) | 0.0318 (17) | −0.0027 (15) | 0.0186 (16) | −0.0007 (14) |
C6 | 0.040 (2) | 0.0222 (17) | 0.0283 (16) | −0.0010 (14) | 0.0139 (14) | −0.0038 (14) |
C7 | 0.0408 (19) | 0.0166 (16) | 0.0230 (15) | 0.0026 (14) | 0.0124 (13) | −0.0036 (12) |
C8 | 0.039 (2) | 0.0179 (16) | 0.0240 (15) | 0.0002 (14) | 0.0123 (14) | −0.0043 (13) |
C9 | 0.0325 (18) | 0.0204 (17) | 0.0295 (16) | 0.0035 (14) | 0.0121 (14) | −0.0003 (13) |
C10 | 0.041 (2) | 0.029 (2) | 0.0325 (18) | 0.0018 (16) | 0.0035 (15) | 0.0015 (15) |
C11 | 0.045 (2) | 0.0174 (17) | 0.0326 (17) | −0.0061 (15) | 0.0078 (15) | −0.0015 (14) |
C12 | 0.0403 (19) | 0.0188 (17) | 0.0282 (16) | 0.0010 (14) | 0.0110 (14) | −0.0036 (13) |
C13 | 0.058 (2) | 0.0215 (18) | 0.0340 (18) | 0.0034 (16) | 0.0197 (17) | −0.0003 (14) |
C14 | 0.053 (2) | 0.0213 (19) | 0.041 (2) | 0.0052 (16) | 0.0212 (17) | 0.0000 (15) |
Geometric parameters (Å, º) top
Ni1—N1i | 2.064 (3) | C5—C6 | 1.389 (5) |
Ni1—N1 | 2.064 (3) | C5—H5 | 0.9500 |
Ni1—N2i | 2.123 (3) | C6—C7 | 1.389 (5) |
Ni1—N2 | 2.123 (3) | C6—H6 | 0.9500 |
Ni1—N3i | 2.141 (3) | C7—C8 | 1.485 (4) |
Ni1—N3 | 2.141 (3) | C9—C10 | 1.489 (5) |
O1—C1 | 1.404 (4) | C9—C11 | 1.491 (5) |
O1—N2 | 1.443 (3) | C10—H10A | 0.9800 |
O2—C1 | 1.422 (4) | C10—H10B | 0.9800 |
O2—N3 | 1.437 (3) | C10—H10C | 0.9800 |
O3—N5 | 1.223 (4) | C10—H10D | 0.9800 |
O4—N5 | 1.250 (4) | C10—H10E | 0.9800 |
O5—N5 | 1.258 (4) | C10—H10F | 0.9800 |
N1—C8 | 1.316 (4) | C11—H11A | 0.9800 |
N1—C1 | 1.453 (4) | C11—H11B | 0.9800 |
N2—C9 | 1.273 (4) | C11—H11C | 0.9800 |
N3—C12 | 1.284 (4) | C12—C13 | 1.485 (5) |
N4—C8 | 1.318 (5) | C12—C14 | 1.494 (5) |
N4—H4B | 0.88 (4) | C13—H13A | 0.9800 |
N4—H4A | 0.93 (6) | C13—H13B | 0.9800 |
C1—C2 | 1.507 (4) | C13—H13C | 0.9800 |
C2—C3 | 1.384 (5) | C14—H14A | 0.9800 |
C2—C7 | 1.390 (5) | C14—H14B | 0.9800 |
C3—C4 | 1.396 (5) | C14—H14C | 0.9800 |
C3—H3 | 0.9500 | C14—H14D | 0.9800 |
C4—C5 | 1.391 (6) | C14—H14E | 0.9800 |
C4—H4 | 0.9500 | C14—H14F | 0.9800 |
| | | |
N1i—Ni1—N1 | 179.999 (1) | N2—C9—C11 | 118.0 (3) |
N1i—Ni1—N2i | 76.95 (10) | C10—C9—C11 | 119.3 (3) |
N1—Ni1—N2i | 103.05 (10) | C9—C10—H10A | 109.5 |
N1i—Ni1—N2 | 103.05 (10) | C9—C10—H10B | 109.5 |
N1—Ni1—N2 | 76.95 (10) | H10A—C10—H10B | 109.5 |
N2i—Ni1—N2 | 180.0 | C9—C10—H10C | 109.5 |
N1i—Ni1—N3i | 77.40 (10) | H10A—C10—H10C | 109.5 |
N1—Ni1—N3i | 102.60 (10) | H10B—C10—H10C | 109.5 |
N2i—Ni1—N3i | 83.94 (10) | C9—C10—H10D | 109.5 |
N2—Ni1—N3i | 96.06 (10) | H10A—C10—H10D | 141.1 |
N1i—Ni1—N3 | 102.60 (10) | H10B—C10—H10D | 56.3 |
N1—Ni1—N3 | 77.40 (10) | H10C—C10—H10D | 56.3 |
N2i—Ni1—N3 | 96.06 (10) | C9—C10—H10E | 109.5 |
N2—Ni1—N3 | 83.94 (10) | H10A—C10—H10E | 56.3 |
N3i—Ni1—N3 | 179.997 (1) | H10B—C10—H10E | 141.1 |
C1—O1—N2 | 110.0 (2) | H10C—C10—H10E | 56.3 |
C1—O2—N3 | 109.3 (2) | H10D—C10—H10E | 109.5 |
C8—N1—C1 | 108.9 (3) | C9—C10—H10F | 109.5 |
C8—N1—Ni1 | 151.1 (2) | H10A—C10—H10F | 56.3 |
C1—N1—Ni1 | 100.03 (19) | H10B—C10—H10F | 56.3 |
C9—N2—O1 | 110.7 (3) | H10C—C10—H10F | 141.1 |
C9—N2—Ni1 | 139.5 (2) | H10D—C10—H10F | 109.5 |
O1—N2—Ni1 | 109.64 (18) | H10E—C10—H10F | 109.5 |
C12—N3—O2 | 110.4 (3) | C9—C11—H11A | 109.5 |
C12—N3—Ni1 | 139.7 (2) | C9—C11—H11B | 109.5 |
O2—N3—Ni1 | 109.86 (17) | H11A—C11—H11B | 109.5 |
C8—N4—H4B | 120 (3) | C9—C11—H11C | 109.5 |
C8—N4—H4A | 117 (3) | H11A—C11—H11C | 109.5 |
H4B—N4—H4A | 122 (4) | H11B—C11—H11C | 109.5 |
O3—N5—O4 | 122.2 (3) | N3—C12—C13 | 118.2 (3) |
O3—N5—O5 | 118.3 (3) | N3—C12—C14 | 123.0 (3) |
O4—N5—O5 | 119.5 (3) | C13—C12—C14 | 118.8 (3) |
O1—C1—O2 | 110.0 (3) | C12—C13—H13A | 109.5 |
O1—C1—N1 | 111.5 (3) | C12—C13—H13B | 109.5 |
O2—C1—N1 | 110.7 (2) | H13A—C13—H13B | 109.5 |
O1—C1—C2 | 109.9 (2) | C12—C13—H13C | 109.5 |
O2—C1—C2 | 108.5 (2) | H13A—C13—H13C | 109.5 |
N1—C1—C2 | 106.1 (3) | H13B—C13—H13C | 109.5 |
C3—C2—C7 | 121.7 (3) | C12—C14—H14A | 109.5 |
C3—C2—C1 | 131.3 (3) | C12—C14—H14B | 109.5 |
C7—C2—C1 | 106.9 (3) | H14A—C14—H14B | 109.5 |
C2—C3—C4 | 116.3 (3) | C12—C14—H14C | 109.5 |
C2—C3—H3 | 121.8 | H14A—C14—H14C | 109.5 |
C4—C3—H3 | 121.8 | H14B—C14—H14C | 109.5 |
C5—C4—C3 | 122.2 (3) | C12—C14—H14D | 109.5 |
C5—C4—H4 | 118.9 | H14A—C14—H14D | 141.1 |
C3—C4—H4 | 118.9 | H14B—C14—H14D | 56.3 |
C6—C5—C4 | 120.9 (3) | H14C—C14—H14D | 56.3 |
C6—C5—H5 | 119.5 | C12—C14—H14E | 109.5 |
C4—C5—H5 | 119.5 | H14A—C14—H14E | 56.3 |
C5—C6—C7 | 117.1 (3) | H14B—C14—H14E | 141.1 |
C5—C6—H6 | 121.5 | H14C—C14—H14E | 56.3 |
C7—C6—H6 | 121.5 | H14D—C14—H14E | 109.5 |
C6—C7—C2 | 121.7 (3) | C12—C14—H14F | 109.5 |
C6—C7—C8 | 131.6 (3) | H14A—C14—H14F | 56.3 |
C2—C7—C8 | 106.6 (3) | H14B—C14—H14F | 56.3 |
N1—C8—N4 | 126.0 (3) | H14C—C14—H14F | 141.1 |
N1—C8—C7 | 111.5 (3) | H14D—C14—H14F | 109.5 |
N4—C8—C7 | 122.5 (3) | H14E—C14—H14F | 109.5 |
N2—C9—C10 | 122.8 (3) | | |
Symmetry code: (i) −x+2, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4B···O5i | 0.88 (4) | 1.97 (4) | 2.783 (4) | 153 (4) |
N4—H4A···O4ii | 0.93 (6) | 2.03 (6) | 2.915 (5) | 159 (5) |
N4—H4B···O4i | 0.88 (4) | 2.75 (4) | 3.492 (5) | 143 (3) |
N4—H4B···N5i | 0.88 (4) | 2.72 (4) | 3.566 (4) | 161 (3) |
N4—H4A···N5ii | 0.93 (6) | 2.72 (5) | 3.449 (4) | 136 (4) |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x+1, y, z. |