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In the title mononuclear nickel(II) compound, [Ni(C13H19N3O3)2(CH4O)2](NO3)2, the NiII 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042807/rz6163sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042807/rz6163Isup2.hkl
Contains datablock I

CCDC reference: 298529

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Computing details top

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)2Z = 1
Mr = 777.44F(000) = 410
Triclinic, P1Dx = 1.434 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.351 (1) ÅCell parameters from 2165 reflections
b = 11.000 (1) Åθ = 2.5–24.3°
c = 11.097 (1) ŵ = 0.62 mm1
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 tube2804 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
Tmin = 0.930, Tmax = 0.941k = 1314
7414 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H 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 parametersΔρmax = 1.18 e Å3
27 restraintsΔρmin = 0.59 e Å3
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
xyzUiso*/UeqOcc. (<1)
Ni10.00001.00001.00000.0382 (3)
O10.1688 (4)0.8537 (2)1.0820 (3)0.0547 (7)
O20.1667 (4)0.8700 (3)1.0919 (3)0.0618 (8)
O30.3209 (6)0.3459 (3)1.0190 (5)0.0953 (13)
O40.1218 (6)0.4214 (3)0.8319 (4)0.0888 (12)
O50.8211 (4)0.2173 (5)0.4921 (4)0.0991 (13)
O60.6556 (11)0.3200 (11)0.3900 (8)0.108 (4)0.536 (16)
O70.5582 (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)
N10.0964 (4)0.9458 (3)0.8301 (3)0.0420 (7)
N20.2559 (4)1.2182 (3)0.4995 (4)0.0559 (9)
N30.2169 (6)0.4313 (3)0.9378 (5)0.0671 (11)
N40.6748 (5)0.2335 (4)0.4973 (5)0.0701 (11)
C10.0671 (5)0.7452 (3)0.9206 (4)0.0417 (8)
C20.1775 (5)0.7577 (3)1.0440 (4)0.0440 (9)
C30.3042 (6)0.6605 (4)1.1268 (4)0.0580 (11)
H30.38090.66901.20570.070*
C40.3156 (6)0.5546 (4)1.0930 (5)0.0598 (11)
H40.39720.49021.15000.072*
C50.2048 (6)0.5435 (3)0.9729 (5)0.0524 (10)
C60.0828 (5)0.6352 (3)0.8876 (4)0.0473 (9)
H60.01010.62550.80790.057*
C70.0607 (5)0.8392 (3)0.8223 (4)0.0442 (9)
H70.12410.82060.74490.053*
C80.2269 (5)1.0282 (4)0.7111 (4)0.0473 (9)
H8A0.28580.97880.65300.057*
H8B0.30911.05730.74020.057*
C90.1431 (6)1.1444 (5)0.6338 (4)0.0659 (13)
H9A0.04491.11460.62310.079*
H9B0.10371.20160.68650.079*
C100.2096 (9)1.3534 (5)0.4415 (8)0.108 (2)
H10A0.26951.38510.34490.130*
H10B0.08921.35670.45300.130*
C110.2480 (11)1.4389 (7)0.5026 (9)0.128 (3)
H11A0.20191.40200.59960.192*
H11B0.19881.52240.47110.192*
H11C0.36861.44880.47750.192*
C120.2510 (9)1.1455 (8)0.3970 (6)0.110 (2)
H12A0.25301.05240.44340.133*
H12B0.14411.16490.37770.133*
C130.3791 (10)1.1774 (8)0.2766 (7)0.125 (3)
H13A0.36111.26300.21890.188*
H13B0.38111.11560.23310.188*
H13C0.48531.17610.29310.188*
C140.3103 (8)0.8959 (6)1.1131 (8)0.106 (2)
H14A0.40560.90341.03370.158*
H14B0.32860.82641.18930.158*
H14C0.29710.97601.13130.158*
H2A0.365 (2)1.212 (5)0.496 (5)0.080*
H20.176 (7)0.800 (3)1.075 (5)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0458 (4)0.0298 (3)0.0372 (4)0.0059 (3)0.0062 (3)0.0136 (3)
O10.0621 (18)0.0440 (14)0.0545 (16)0.0150 (13)0.0011 (14)0.0239 (12)
O20.074 (2)0.0482 (16)0.080 (2)0.0141 (15)0.0384 (17)0.0319 (15)
O30.114 (3)0.051 (2)0.134 (3)0.021 (2)0.052 (3)0.030 (2)
O40.131 (3)0.056 (2)0.107 (3)0.010 (2)0.052 (3)0.049 (2)
O50.045 (2)0.148 (4)0.118 (3)0.005 (2)0.029 (2)0.060 (3)
O60.099 (7)0.113 (9)0.091 (6)0.001 (6)0.028 (5)0.012 (5)
O70.064 (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)
N10.0486 (19)0.0373 (15)0.0382 (16)0.0002 (13)0.0098 (14)0.0140 (12)
N20.044 (2)0.0528 (19)0.0518 (19)0.0025 (16)0.0074 (17)0.0011 (15)
N30.090 (3)0.0361 (19)0.099 (3)0.006 (2)0.061 (3)0.023 (2)
N40.057 (3)0.072 (3)0.093 (3)0.012 (2)0.027 (3)0.041 (3)
C10.049 (2)0.0324 (16)0.047 (2)0.0009 (15)0.0197 (17)0.0133 (15)
C20.047 (2)0.0365 (18)0.050 (2)0.0057 (16)0.0164 (17)0.0130 (15)
C30.060 (3)0.052 (2)0.057 (2)0.014 (2)0.010 (2)0.0159 (19)
C40.066 (3)0.042 (2)0.073 (3)0.0110 (19)0.029 (2)0.011 (2)
C50.067 (3)0.0312 (18)0.076 (3)0.0036 (18)0.044 (2)0.0185 (18)
C60.059 (3)0.0364 (19)0.056 (2)0.0046 (17)0.029 (2)0.0182 (17)
C70.053 (2)0.0412 (19)0.0412 (19)0.0006 (16)0.0129 (17)0.0187 (15)
C80.048 (2)0.044 (2)0.043 (2)0.0001 (17)0.0042 (17)0.0154 (16)
C90.053 (3)0.071 (3)0.049 (2)0.003 (2)0.004 (2)0.002 (2)
C100.089 (4)0.066 (4)0.135 (6)0.002 (3)0.029 (4)0.001 (4)
C110.163 (7)0.092 (5)0.185 (8)0.036 (5)0.104 (6)0.078 (5)
C120.111 (5)0.141 (6)0.069 (4)0.011 (5)0.025 (4)0.023 (4)
C130.135 (6)0.169 (7)0.089 (5)0.059 (6)0.053 (5)0.064 (5)
C140.081 (4)0.081 (4)0.170 (7)0.004 (3)0.059 (5)0.043 (4)
Geometric parameters (Å, º) top
Ni1—O11.999 (3)C3—C41.366 (6)
Ni1—O1i1.999 (3)C3—H30.9300
Ni1—N1i2.066 (3)C4—C51.392 (6)
Ni1—N12.066 (3)C4—H40.9300
Ni1—O22.120 (3)C5—C61.361 (6)
Ni1—O2i2.120 (3)C6—H60.9300
O1—C21.285 (4)C7—H70.9300
O2—C141.371 (7)C8—C91.511 (6)
O2—H20.85 (4)C8—H8A0.9700
O3—N31.227 (5)C8—H8B0.9700
O4—N31.220 (6)C9—H9A0.9700
O5—N41.202 (4)C9—H9B0.9700
O6—N41.277 (6)C10—C111.451 (9)
O7—N41.165 (6)C10—H10A0.9700
O6'—N41.186 (6)C10—H10B0.9700
O7'—N41.271 (6)C11—H11A0.9600
N1—C71.278 (5)C11—H11B0.9600
N1—C81.471 (5)C11—H11C0.9600
N2—C101.461 (6)C12—C131.366 (8)
N2—C91.465 (5)C12—H12A0.9700
N2—C121.618 (8)C12—H12B0.9700
N2—H2A0.90 (3)C13—H13A0.9600
N3—C51.442 (5)C13—H13B0.9600
C1—C61.412 (5)C13—H13C0.9600
C1—C21.424 (5)C14—H14A0.9600
C1—C71.437 (5)C14—H14B0.9600
C2—C31.416 (6)C14—H14C0.9600
O1—Ni1—O1i180.0C5—C4—H4120.1
O1—Ni1—N1i90.79 (11)C6—C5—C4121.8 (4)
O1i—Ni1—N1i89.21 (11)C6—C5—N3118.7 (4)
O1—Ni1—N189.21 (11)C4—C5—N3119.5 (4)
O1i—Ni1—N190.79 (11)C5—C6—C1119.7 (4)
N1i—Ni1—N1180.0C5—C6—H6120.1
O1—Ni1—O288.13 (13)C1—C6—H6120.1
O1i—Ni1—O291.87 (13)N1—C7—C1126.7 (3)
N1i—Ni1—O290.04 (12)N1—C7—H7116.6
N1—Ni1—O289.96 (12)C1—C7—H7116.6
O1—Ni1—O2i91.87 (13)N1—C8—C9109.0 (3)
O1i—Ni1—O2i88.13 (13)N1—C8—H8A109.9
N1i—Ni1—O2i89.96 (12)C9—C8—H8A109.9
N1—Ni1—O2i90.04 (12)N1—C8—H8B109.9
O2—Ni1—O2i180.0C9—C8—H8B109.9
C2—O1—Ni1130.1 (2)H8A—C8—H8B108.3
C14—O2—Ni1129.7 (3)N2—C9—C8113.2 (3)
C14—O2—H2111 (4)N2—C9—H9A108.9
Ni1—O2—H2111 (4)C8—C9—H9A108.9
C7—N1—C8115.6 (3)N2—C9—H9B108.9
C7—N1—Ni1124.9 (3)C8—C9—H9B108.9
C8—N1—Ni1119.3 (2)H9A—C9—H9B107.8
C10—N2—C9115.7 (4)C11—C10—N2113.4 (6)
C10—N2—C12106.8 (5)C11—C10—H10A108.9
C9—N2—C12106.9 (4)N2—C10—H10A108.9
C10—N2—H2A111 (3)C11—C10—H10B108.9
C9—N2—H2A113 (3)N2—C10—H10B108.9
C12—N2—H2A102 (3)H10A—C10—H10B107.7
O4—N3—O3121.8 (4)C10—C11—H11A109.5
O4—N3—C5120.1 (4)C10—C11—H11B109.5
O3—N3—C5118.1 (5)H11A—C11—H11B109.5
O7—N4—O6'63.2 (8)C10—C11—H11C109.5
O7—N4—O5129.3 (6)H11A—C11—H11C109.5
O6'—N4—O5127.4 (6)H11B—C11—H11C109.5
O7—N4—O7'58.4 (8)C13—C12—N2115.9 (6)
O6'—N4—O7'111.3 (7)C13—C12—H12A108.3
O5—N4—O7'116.6 (6)N2—C12—H12A108.3
O7—N4—O6115.3 (7)C13—C12—H12B108.3
O6'—N4—O665.6 (8)N2—C12—H12B108.3
O5—N4—O6112.5 (6)H12A—C12—H12B107.4
O7'—N4—O6111.4 (8)C12—C13—H13A109.5
C6—C1—C2119.5 (4)C12—C13—H13B109.5
C6—C1—C7115.9 (3)H13A—C13—H13B109.5
C2—C1—C7124.6 (3)C12—C13—H13C109.5
O1—C2—C3118.9 (3)H13A—C13—H13C109.5
O1—C2—C1123.1 (3)H13B—C13—H13C109.5
C3—C2—C1118.1 (3)O2—C14—H14A109.5
C4—C3—C2121.1 (4)O2—C14—H14B109.5
C4—C3—H3119.4H14A—C14—H14B109.5
C2—C3—H3119.4O2—C14—H14C109.5
C3—C4—C5119.7 (4)H14A—C14—H14C109.5
C3—C4—H4120.1H14B—C14—H14C109.5
Symmetry code: (i) x, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N3ii0.85 (4)2.58 (4)3.416 (5)170 (5)
O2—H2···O4ii0.85 (4)2.31 (3)3.039 (4)145 (4)
O2—H2···O3ii0.85 (4)2.26 (3)3.038 (5)154 (5)
N2—H2A···N4iii0.90 (3)2.63 (2)3.511 (5)169 (4)
N2—H2A···O7iii0.90 (3)2.55 (3)3.317 (11)143 (4)
N2—H2A···O6iii0.90 (3)2.53 (3)3.321 (11)147 (4)
N2—H2A···O7iii0.90 (3)1.96 (2)2.803 (10)157 (4)
N2—H2A···O6iii0.90 (3)1.88 (2)2.749 (9)164 (5)
Symmetry codes: (ii) x, y+1, z+2; (iii) x, y+1, z.
 

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