In the title mononuclear nickel(II) compound, [Ni(C
13H
19N
3O
3)
2(CH
4O)
2](NO
3)
2, the Ni
II atom is coordinated by two N and four O atoms, giving an octahedral geometry. The cationic complex lies on a centre of symmetry. In the crystal structure, the molecules are linked through intermolecular O—H
O, N—H
N and N—H
O hydrogen bonds, forming chains running along the
b axis.
Supporting information
CCDC reference: 298529
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.064
- wR factor = 0.180
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N2
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 27.49
From the CIF: _diffrn_reflns_theta_full 27.49
From the CIF: _reflns_number_total 3889
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 4133
Completeness (_total/calc) 94.10%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.07 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.62 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C12 - C13 ... 1.37 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O7 .. C8 .. 2.95 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Bis{2-[2-(diethylamminio)ethyliminomethyl]-4-
nitrophenolato}dimethanolnickel(II) dinitrate
top
Crystal data top
[Ni(C13H19N3O3)2(CH4O)2](NO3)2 | Z = 1 |
Mr = 777.44 | F(000) = 410 |
Triclinic, P1 | Dx = 1.434 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.351 (1) Å | Cell parameters from 2165 reflections |
b = 11.000 (1) Å | θ = 2.5–24.3° |
c = 11.097 (1) Å | µ = 0.62 mm−1 |
α = 69.092 (2)° | T = 298 K |
β = 70.963 (2)° | Block, green |
γ = 84.048 (2)° | 0.12 × 0.11 × 0.10 mm |
V = 900.09 (16) Å3 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3889 independent reflections |
Radiation source: fine-focus sealed tube | 2804 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→10 |
Tmin = 0.930, Tmax = 0.941 | k = −13→14 |
7414 measured reflections | l = −14→14 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.180 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1069P)2] where P = (Fo2 + 2Fc2)/3 |
3889 reflections | (Δ/σ)max < 0.001 |
260 parameters | Δρmax = 1.18 e Å−3 |
27 restraints | Δρmin = −0.59 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 | 0.0000 | 1.0000 | 1.0000 | 0.0382 (3) | |
O1 | −0.1688 (4) | 0.8537 (2) | 1.0820 (3) | 0.0547 (7) | |
O2 | 0.1667 (4) | 0.8700 (3) | 1.0919 (3) | 0.0618 (8) | |
O3 | −0.3209 (6) | 0.3459 (3) | 1.0190 (5) | 0.0953 (13) | |
O4 | −0.1218 (6) | 0.4214 (3) | 0.8319 (4) | 0.0888 (12) | |
O5 | 0.8211 (4) | 0.2173 (5) | 0.4921 (4) | 0.0991 (13) | |
O6 | 0.6556 (11) | 0.3200 (11) | 0.3900 (8) | 0.108 (4) | 0.536 (16) |
O7 | 0.5582 (10) | 0.1648 (11) | 0.5660 (14) | 0.136 (8) | 0.536 (16) |
O6' | 0.6015 (10) | 0.1962 (16) | 0.4414 (14) | 0.113 (7) | 0.464 (16) |
O7' | 0.5738 (12) | 0.2504 (16) | 0.6037 (9) | 0.099 (4) | 0.464 (16) |
N1 | 0.0964 (4) | 0.9458 (3) | 0.8301 (3) | 0.0420 (7) | |
N2 | 0.2559 (4) | 1.2182 (3) | 0.4995 (4) | 0.0559 (9) | |
N3 | −0.2169 (6) | 0.4313 (3) | 0.9378 (5) | 0.0671 (11) | |
N4 | 0.6748 (5) | 0.2335 (4) | 0.4973 (5) | 0.0701 (11) | |
C1 | −0.0671 (5) | 0.7452 (3) | 0.9206 (4) | 0.0417 (8) | |
C2 | −0.1775 (5) | 0.7577 (3) | 1.0440 (4) | 0.0440 (9) | |
C3 | −0.3042 (6) | 0.6605 (4) | 1.1268 (4) | 0.0580 (11) | |
H3 | −0.3809 | 0.6690 | 1.2057 | 0.070* | |
C4 | −0.3156 (6) | 0.5546 (4) | 1.0930 (5) | 0.0598 (11) | |
H4 | −0.3972 | 0.4902 | 1.1500 | 0.072* | |
C5 | −0.2048 (6) | 0.5435 (3) | 0.9729 (5) | 0.0524 (10) | |
C6 | −0.0828 (5) | 0.6352 (3) | 0.8876 (4) | 0.0473 (9) | |
H6 | −0.0101 | 0.6255 | 0.8079 | 0.057* | |
C7 | 0.0607 (5) | 0.8392 (3) | 0.8223 (4) | 0.0442 (9) | |
H7 | 0.1241 | 0.8206 | 0.7449 | 0.053* | |
C8 | 0.2269 (5) | 1.0282 (4) | 0.7111 (4) | 0.0473 (9) | |
H8A | 0.2858 | 0.9788 | 0.6530 | 0.057* | |
H8B | 0.3091 | 1.0573 | 0.7402 | 0.057* | |
C9 | 0.1431 (6) | 1.1444 (5) | 0.6338 (4) | 0.0659 (13) | |
H9A | 0.0449 | 1.1146 | 0.6231 | 0.079* | |
H9B | 0.1037 | 1.2016 | 0.6865 | 0.079* | |
C10 | 0.2096 (9) | 1.3534 (5) | 0.4415 (8) | 0.108 (2) | |
H10A | 0.2695 | 1.3851 | 0.3449 | 0.130* | |
H10B | 0.0892 | 1.3567 | 0.4530 | 0.130* | |
C11 | 0.2480 (11) | 1.4389 (7) | 0.5026 (9) | 0.128 (3) | |
H11A | 0.2019 | 1.4020 | 0.5996 | 0.192* | |
H11B | 0.1988 | 1.5224 | 0.4711 | 0.192* | |
H11C | 0.3686 | 1.4488 | 0.4775 | 0.192* | |
C12 | 0.2510 (9) | 1.1455 (8) | 0.3970 (6) | 0.110 (2) | |
H12A | 0.2530 | 1.0524 | 0.4434 | 0.133* | |
H12B | 0.1441 | 1.1649 | 0.3777 | 0.133* | |
C13 | 0.3791 (10) | 1.1774 (8) | 0.2766 (7) | 0.125 (3) | |
H13A | 0.3611 | 1.2630 | 0.2189 | 0.188* | |
H13B | 0.3811 | 1.1156 | 0.2331 | 0.188* | |
H13C | 0.4853 | 1.1761 | 0.2931 | 0.188* | |
C14 | 0.3103 (8) | 0.8959 (6) | 1.1131 (8) | 0.106 (2) | |
H14A | 0.4056 | 0.9034 | 1.0337 | 0.158* | |
H14B | 0.3286 | 0.8264 | 1.1893 | 0.158* | |
H14C | 0.2971 | 0.9760 | 1.1313 | 0.158* | |
H2A | 0.365 (2) | 1.212 (5) | 0.496 (5) | 0.080* | |
H2 | 0.176 (7) | 0.800 (3) | 1.075 (5) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0458 (4) | 0.0298 (3) | 0.0372 (4) | −0.0059 (3) | −0.0062 (3) | −0.0136 (3) |
O1 | 0.0621 (18) | 0.0440 (14) | 0.0545 (16) | −0.0150 (13) | −0.0011 (14) | −0.0239 (12) |
O2 | 0.074 (2) | 0.0482 (16) | 0.080 (2) | 0.0141 (15) | −0.0384 (17) | −0.0319 (15) |
O3 | 0.114 (3) | 0.051 (2) | 0.134 (3) | −0.021 (2) | −0.052 (3) | −0.030 (2) |
O4 | 0.131 (3) | 0.056 (2) | 0.107 (3) | 0.010 (2) | −0.052 (3) | −0.049 (2) |
O5 | 0.045 (2) | 0.148 (4) | 0.118 (3) | 0.005 (2) | −0.029 (2) | −0.060 (3) |
O6 | 0.099 (7) | 0.113 (9) | 0.091 (6) | −0.001 (6) | −0.028 (5) | −0.012 (5) |
O7 | 0.064 (6) | 0.119 (10) | 0.152 (13) | −0.036 (6) | −0.025 (6) | 0.042 (10) |
O6' | 0.059 (6) | 0.189 (19) | 0.151 (12) | 0.011 (8) | −0.030 (7) | −0.132 (14) |
O7' | 0.077 (7) | 0.145 (11) | 0.075 (6) | −0.006 (6) | −0.005 (5) | −0.053 (6) |
N1 | 0.0486 (19) | 0.0373 (15) | 0.0382 (16) | 0.0002 (13) | −0.0098 (14) | −0.0140 (12) |
N2 | 0.044 (2) | 0.0528 (19) | 0.0518 (19) | −0.0025 (16) | −0.0074 (17) | −0.0011 (15) |
N3 | 0.090 (3) | 0.0361 (19) | 0.099 (3) | 0.006 (2) | −0.061 (3) | −0.023 (2) |
N4 | 0.057 (3) | 0.072 (3) | 0.093 (3) | 0.012 (2) | −0.027 (3) | −0.041 (3) |
C1 | 0.049 (2) | 0.0324 (16) | 0.047 (2) | 0.0009 (15) | −0.0197 (17) | −0.0133 (15) |
C2 | 0.047 (2) | 0.0365 (18) | 0.050 (2) | −0.0057 (16) | −0.0164 (17) | −0.0130 (15) |
C3 | 0.060 (3) | 0.052 (2) | 0.057 (2) | −0.014 (2) | −0.010 (2) | −0.0159 (19) |
C4 | 0.066 (3) | 0.042 (2) | 0.073 (3) | −0.0110 (19) | −0.029 (2) | −0.011 (2) |
C5 | 0.067 (3) | 0.0312 (18) | 0.076 (3) | 0.0036 (18) | −0.044 (2) | −0.0185 (18) |
C6 | 0.059 (3) | 0.0364 (19) | 0.056 (2) | 0.0046 (17) | −0.029 (2) | −0.0182 (17) |
C7 | 0.053 (2) | 0.0412 (19) | 0.0412 (19) | 0.0006 (16) | −0.0129 (17) | −0.0187 (15) |
C8 | 0.048 (2) | 0.044 (2) | 0.043 (2) | −0.0001 (17) | −0.0042 (17) | −0.0154 (16) |
C9 | 0.053 (3) | 0.071 (3) | 0.049 (2) | −0.003 (2) | −0.004 (2) | −0.002 (2) |
C10 | 0.089 (4) | 0.066 (4) | 0.135 (6) | −0.002 (3) | −0.029 (4) | 0.001 (4) |
C11 | 0.163 (7) | 0.092 (5) | 0.185 (8) | 0.036 (5) | −0.104 (6) | −0.078 (5) |
C12 | 0.111 (5) | 0.141 (6) | 0.069 (4) | −0.011 (5) | −0.025 (4) | −0.023 (4) |
C13 | 0.135 (6) | 0.169 (7) | 0.089 (5) | 0.059 (6) | −0.053 (5) | −0.064 (5) |
C14 | 0.081 (4) | 0.081 (4) | 0.170 (7) | 0.004 (3) | −0.059 (5) | −0.043 (4) |
Geometric parameters (Å, º) top
Ni1—O1 | 1.999 (3) | C3—C4 | 1.366 (6) |
Ni1—O1i | 1.999 (3) | C3—H3 | 0.9300 |
Ni1—N1i | 2.066 (3) | C4—C5 | 1.392 (6) |
Ni1—N1 | 2.066 (3) | C4—H4 | 0.9300 |
Ni1—O2 | 2.120 (3) | C5—C6 | 1.361 (6) |
Ni1—O2i | 2.120 (3) | C6—H6 | 0.9300 |
O1—C2 | 1.285 (4) | C7—H7 | 0.9300 |
O2—C14 | 1.371 (7) | C8—C9 | 1.511 (6) |
O2—H2 | 0.85 (4) | C8—H8A | 0.9700 |
O3—N3 | 1.227 (5) | C8—H8B | 0.9700 |
O4—N3 | 1.220 (6) | C9—H9A | 0.9700 |
O5—N4 | 1.202 (4) | C9—H9B | 0.9700 |
O6—N4 | 1.277 (6) | C10—C11 | 1.451 (9) |
O7—N4 | 1.165 (6) | C10—H10A | 0.9700 |
O6'—N4 | 1.186 (6) | C10—H10B | 0.9700 |
O7'—N4 | 1.271 (6) | C11—H11A | 0.9600 |
N1—C7 | 1.278 (5) | C11—H11B | 0.9600 |
N1—C8 | 1.471 (5) | C11—H11C | 0.9600 |
N2—C10 | 1.461 (6) | C12—C13 | 1.366 (8) |
N2—C9 | 1.465 (5) | C12—H12A | 0.9700 |
N2—C12 | 1.618 (8) | C12—H12B | 0.9700 |
N2—H2A | 0.90 (3) | C13—H13A | 0.9600 |
N3—C5 | 1.442 (5) | C13—H13B | 0.9600 |
C1—C6 | 1.412 (5) | C13—H13C | 0.9600 |
C1—C2 | 1.424 (5) | C14—H14A | 0.9600 |
C1—C7 | 1.437 (5) | C14—H14B | 0.9600 |
C2—C3 | 1.416 (6) | C14—H14C | 0.9600 |
| | | |
O1—Ni1—O1i | 180.0 | C5—C4—H4 | 120.1 |
O1—Ni1—N1i | 90.79 (11) | C6—C5—C4 | 121.8 (4) |
O1i—Ni1—N1i | 89.21 (11) | C6—C5—N3 | 118.7 (4) |
O1—Ni1—N1 | 89.21 (11) | C4—C5—N3 | 119.5 (4) |
O1i—Ni1—N1 | 90.79 (11) | C5—C6—C1 | 119.7 (4) |
N1i—Ni1—N1 | 180.0 | C5—C6—H6 | 120.1 |
O1—Ni1—O2 | 88.13 (13) | C1—C6—H6 | 120.1 |
O1i—Ni1—O2 | 91.87 (13) | N1—C7—C1 | 126.7 (3) |
N1i—Ni1—O2 | 90.04 (12) | N1—C7—H7 | 116.6 |
N1—Ni1—O2 | 89.96 (12) | C1—C7—H7 | 116.6 |
O1—Ni1—O2i | 91.87 (13) | N1—C8—C9 | 109.0 (3) |
O1i—Ni1—O2i | 88.13 (13) | N1—C8—H8A | 109.9 |
N1i—Ni1—O2i | 89.96 (12) | C9—C8—H8A | 109.9 |
N1—Ni1—O2i | 90.04 (12) | N1—C8—H8B | 109.9 |
O2—Ni1—O2i | 180.0 | C9—C8—H8B | 109.9 |
C2—O1—Ni1 | 130.1 (2) | H8A—C8—H8B | 108.3 |
C14—O2—Ni1 | 129.7 (3) | N2—C9—C8 | 113.2 (3) |
C14—O2—H2 | 111 (4) | N2—C9—H9A | 108.9 |
Ni1—O2—H2 | 111 (4) | C8—C9—H9A | 108.9 |
C7—N1—C8 | 115.6 (3) | N2—C9—H9B | 108.9 |
C7—N1—Ni1 | 124.9 (3) | C8—C9—H9B | 108.9 |
C8—N1—Ni1 | 119.3 (2) | H9A—C9—H9B | 107.8 |
C10—N2—C9 | 115.7 (4) | C11—C10—N2 | 113.4 (6) |
C10—N2—C12 | 106.8 (5) | C11—C10—H10A | 108.9 |
C9—N2—C12 | 106.9 (4) | N2—C10—H10A | 108.9 |
C10—N2—H2A | 111 (3) | C11—C10—H10B | 108.9 |
C9—N2—H2A | 113 (3) | N2—C10—H10B | 108.9 |
C12—N2—H2A | 102 (3) | H10A—C10—H10B | 107.7 |
O4—N3—O3 | 121.8 (4) | C10—C11—H11A | 109.5 |
O4—N3—C5 | 120.1 (4) | C10—C11—H11B | 109.5 |
O3—N3—C5 | 118.1 (5) | H11A—C11—H11B | 109.5 |
O7—N4—O6' | 63.2 (8) | C10—C11—H11C | 109.5 |
O7—N4—O5 | 129.3 (6) | H11A—C11—H11C | 109.5 |
O6'—N4—O5 | 127.4 (6) | H11B—C11—H11C | 109.5 |
O7—N4—O7' | 58.4 (8) | C13—C12—N2 | 115.9 (6) |
O6'—N4—O7' | 111.3 (7) | C13—C12—H12A | 108.3 |
O5—N4—O7' | 116.6 (6) | N2—C12—H12A | 108.3 |
O7—N4—O6 | 115.3 (7) | C13—C12—H12B | 108.3 |
O6'—N4—O6 | 65.6 (8) | N2—C12—H12B | 108.3 |
O5—N4—O6 | 112.5 (6) | H12A—C12—H12B | 107.4 |
O7'—N4—O6 | 111.4 (8) | C12—C13—H13A | 109.5 |
C6—C1—C2 | 119.5 (4) | C12—C13—H13B | 109.5 |
C6—C1—C7 | 115.9 (3) | H13A—C13—H13B | 109.5 |
C2—C1—C7 | 124.6 (3) | C12—C13—H13C | 109.5 |
O1—C2—C3 | 118.9 (3) | H13A—C13—H13C | 109.5 |
O1—C2—C1 | 123.1 (3) | H13B—C13—H13C | 109.5 |
C3—C2—C1 | 118.1 (3) | O2—C14—H14A | 109.5 |
C4—C3—C2 | 121.1 (4) | O2—C14—H14B | 109.5 |
C4—C3—H3 | 119.4 | H14A—C14—H14B | 109.5 |
C2—C3—H3 | 119.4 | O2—C14—H14C | 109.5 |
C3—C4—C5 | 119.7 (4) | H14A—C14—H14C | 109.5 |
C3—C4—H4 | 120.1 | H14B—C14—H14C | 109.5 |
Symmetry code: (i) −x, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N3ii | 0.85 (4) | 2.58 (4) | 3.416 (5) | 170 (5) |
O2—H2···O4ii | 0.85 (4) | 2.31 (3) | 3.039 (4) | 145 (4) |
O2—H2···O3ii | 0.85 (4) | 2.26 (3) | 3.038 (5) | 154 (5) |
N2—H2A···N4iii | 0.90 (3) | 2.63 (2) | 3.511 (5) | 169 (4) |
N2—H2A···O7′iii | 0.90 (3) | 2.55 (3) | 3.317 (11) | 143 (4) |
N2—H2A···O6iii | 0.90 (3) | 2.53 (3) | 3.321 (11) | 147 (4) |
N2—H2A···O7iii | 0.90 (3) | 1.96 (2) | 2.803 (10) | 157 (4) |
N2—H2A···O6′iii | 0.90 (3) | 1.88 (2) | 2.749 (9) | 164 (5) |
Symmetry codes: (ii) −x, −y+1, −z+2; (iii) x, y+1, z. |