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The Ni atom in the title complex, [Ni(C7H7N4O)2], is octahedrally coordinated by two mono-deprotonated Schiff bases that are derived from the condensation of pyridine-2-carb­aldehyde and semicarbazide; the Schiff bases act as meridional tridentate ligands, each of them coordinating the metal with the deprotonated amidate oxy­gen [Ni—O = 2.0909 (15) and 2.0959 (15) Å], imine nitro­gen [Ni—N = 1.9892 (18) and 1.9822 (18) Å] and pyridine nitro­gen [Ni—N = 2.100 (2) and 2.1317 (2) Å]. The dihedral angle formed by the mean planes of the bicyclic chelate systems of each of the ligands is equal to 87.69 (4)°. The crystal packing is stabilized by intermolecular hydrogen bonds involving N—H...O and C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008207/ya6201sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008207/ya6201Isup2.hkl
Contains datablock I

CCDC reference: 239053

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.026
  • wR factor = 0.056
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.445 From the CIF: _refine_ls_abs_structure_Flack_su 0.010 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.44 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N8 - H8B ... ? PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 21 N6 -NI1 -N2 -C6 166.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 26 N6 -NI1 -N2 -N3 -12.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 43 N2 -NI1 -N6 -C13 -80.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 48 N2 -NI1 -N6 -N7 100.00 4.00 1.555 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3413 Count of symmetry unique reflns 1901 Completeness (_total/calc) 179.54% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1512 Fraction of Friedel pairs measured 0.795 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku and Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXTL.

Bis(2-formylpyridine semicabazonato)nickel(II) top
Crystal data top
[Ni(C7H7N4O)2]Dx = 1.579 Mg m3
Mr = 385.04Mo Kα radiation, λ = 0.71070 Å
Tetragonal, P43Cell parameters from 8353 reflections
Hall symbol: P 4cwθ = 3.4–27.5°
a = 8.2766 (12) ŵ = 1.22 mm1
c = 23.648 (4) ÅT = 193 K
V = 1619.9 (4) Å3Octahedron, dark-red
Z = 40.54 × 0.37 × 0.30 mm
F(000) = 792
Data collection top
Rigaku Mercury CCD
diffractometer
3413 independent reflections
Radiation source: fine-focus sealed tube3368 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 3.4°
ω scansh = 810
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1010
Tmin = 0.557, Tmax = 0.710l = 3025
18151 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.056 w = 1/[σ2(Fo2) + (0.0203P)2 0.748P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
3413 reflectionsΔρmax = 0.19 e Å3
243 parametersΔρmin = 0.21 e Å3
5 restraintsAbsolute structure: Flack (1983); 1512 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.445 (10)
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*/Ueq
Ni10.55169 (3)0.18766 (3)0.229470 (11)0.01823 (7)
O10.43931 (18)0.03770 (17)0.22241 (7)0.0229 (3)
O20.32805 (18)0.30478 (19)0.23638 (7)0.0250 (3)
N10.6742 (2)0.3746 (2)0.27147 (8)0.0238 (4)
N20.5827 (2)0.0894 (2)0.30547 (7)0.0201 (4)
N30.5253 (2)0.0592 (2)0.31640 (8)0.0262 (4)
N40.3735 (3)0.2569 (3)0.27498 (9)0.0363 (5)
N50.7710 (2)0.1206 (2)0.18844 (8)0.0212 (4)
N60.5194 (2)0.2815 (2)0.15317 (8)0.0206 (4)
N70.3835 (2)0.3673 (3)0.14200 (8)0.0263 (4)
N80.1607 (3)0.4686 (3)0.18623 (10)0.0362 (5)
C10.7164 (4)0.5204 (3)0.25307 (13)0.0369 (6)
H10.68740.55060.21570.044*
C20.7996 (4)0.6291 (4)0.28564 (15)0.0547 (9)
H20.82940.73160.27090.066*
C30.8395 (4)0.5865 (4)0.34060 (15)0.0549 (9)
H30.89490.66060.36440.066*
C40.7980 (3)0.4356 (3)0.36040 (12)0.0375 (6)
H40.82630.40330.39770.045*
C50.7144 (3)0.3321 (3)0.32510 (10)0.0250 (5)
C60.6633 (3)0.1721 (3)0.34262 (10)0.0253 (5)
H60.68740.13040.37910.030*
C70.4466 (3)0.1130 (3)0.26892 (10)0.0229 (4)
C80.9062 (3)0.0532 (3)0.20893 (11)0.0290 (5)
H80.90670.01780.24710.035*
C91.0446 (3)0.0328 (3)0.17716 (12)0.0364 (6)
H91.13810.01560.19310.044*
C101.0440 (3)0.0846 (4)0.12134 (13)0.0391 (6)
H101.13770.07240.09850.047*
C110.9061 (3)0.1539 (3)0.09933 (11)0.0310 (5)
H110.90270.18790.06100.037*
C120.7721 (3)0.1731 (3)0.13406 (10)0.0225 (5)
C130.6286 (3)0.2590 (3)0.11528 (9)0.0251 (5)
H130.61620.29610.07750.030*
C140.2936 (3)0.3741 (3)0.19019 (10)0.0233 (5)
H8B0.087 (3)0.455 (4)0.2133 (11)0.044 (9)*
H4A0.318 (3)0.305 (3)0.2475 (9)0.032 (7)*
H4B0.378 (3)0.305 (3)0.3083 (8)0.029 (7)*
H8A0.131 (4)0.497 (4)0.1517 (9)0.046 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02104 (13)0.02194 (13)0.01171 (11)0.00037 (11)0.00105 (11)0.00198 (11)
O10.0301 (8)0.0235 (7)0.0149 (8)0.0046 (6)0.0006 (7)0.0001 (6)
O20.0249 (7)0.0353 (8)0.0147 (8)0.0052 (6)0.0003 (7)0.0012 (7)
N10.0255 (10)0.0254 (10)0.0205 (10)0.0000 (7)0.0015 (8)0.0014 (8)
N20.0235 (9)0.0218 (9)0.0149 (9)0.0014 (7)0.0005 (7)0.0018 (7)
N30.0378 (11)0.0226 (9)0.0181 (10)0.0066 (8)0.0004 (8)0.0025 (7)
N40.0570 (14)0.0313 (11)0.0205 (12)0.0184 (10)0.0044 (10)0.0023 (9)
N50.0233 (9)0.0221 (9)0.0183 (9)0.0010 (7)0.0022 (7)0.0019 (7)
N60.0215 (9)0.0259 (10)0.0145 (9)0.0022 (7)0.0010 (7)0.0025 (7)
N70.0251 (10)0.0377 (12)0.0160 (10)0.0092 (9)0.0003 (7)0.0030 (8)
N80.0344 (12)0.0532 (14)0.0211 (12)0.0174 (10)0.0026 (9)0.0019 (10)
C10.0497 (17)0.0272 (13)0.0337 (14)0.0072 (11)0.0026 (12)0.0061 (11)
C20.079 (2)0.0319 (16)0.053 (2)0.0275 (15)0.0083 (18)0.0104 (15)
C30.073 (2)0.0461 (18)0.046 (2)0.0316 (16)0.0104 (16)0.0053 (15)
C40.0436 (15)0.0410 (15)0.0280 (14)0.0136 (12)0.0080 (12)0.0027 (11)
C50.0248 (11)0.0284 (11)0.0219 (11)0.0023 (9)0.0016 (9)0.0021 (9)
C60.0328 (13)0.0304 (12)0.0127 (11)0.0029 (10)0.0063 (9)0.0040 (9)
C70.0260 (11)0.0239 (11)0.0189 (11)0.0025 (9)0.0016 (9)0.0002 (9)
C80.0295 (12)0.0290 (12)0.0287 (13)0.0041 (10)0.0058 (10)0.0028 (10)
C90.0256 (13)0.0426 (15)0.0409 (16)0.0109 (10)0.0049 (11)0.0011 (12)
C100.0281 (13)0.0467 (16)0.0426 (17)0.0082 (12)0.0084 (12)0.0011 (13)
C110.0298 (12)0.0372 (13)0.0261 (13)0.0034 (10)0.0069 (10)0.0027 (11)
C120.0234 (11)0.0241 (11)0.0202 (11)0.0006 (9)0.0011 (9)0.0010 (8)
C130.0262 (11)0.0329 (12)0.0160 (12)0.0026 (10)0.0019 (9)0.0041 (9)
C140.0241 (11)0.0307 (12)0.0152 (11)0.0038 (9)0.0023 (9)0.0037 (9)
Geometric parameters (Å, º) top
Ni1—O12.0909 (15)N8—H8B0.888 (18)
Ni1—O22.0959 (15)N8—H8A0.884 (18)
Ni1—N12.100 (2)C1—C21.370 (4)
Ni1—N21.9892 (18)C1—H10.9500
Ni1—N52.1317 (19)C2—C31.387 (5)
Ni1—N61.9822 (18)C2—H20.9500
C7—O11.265 (3)C3—C41.377 (4)
C14—O21.266 (3)C3—H30.9500
N1—C11.330 (3)C4—C51.382 (3)
N1—C51.357 (3)C4—H40.9500
N2—C61.298 (3)C5—C61.451 (3)
N2—N31.344 (3)C6—H60.9500
N3—C71.372 (3)C8—C91.381 (4)
N4—C71.344 (3)C8—H80.9500
N4—H4A0.888 (17)C9—C101.388 (4)
N4—H4B0.883 (17)C9—H90.9500
N5—C81.341 (3)C10—C111.380 (4)
N5—C121.357 (3)C10—H100.9500
N6—C131.286 (3)C11—C121.389 (3)
N6—N71.357 (3)C11—H110.9500
N7—C141.362 (3)C12—C131.454 (3)
N8—C141.353 (3)C13—H130.9500
N1—Ni1—N279.14 (8)C1—C2—C3118.7 (3)
N1—Ni1—N589.77 (7)C1—C2—H2120.7
N1—Ni1—N6101.95 (8)C3—C2—H2120.7
N2—Ni1—N5101.25 (7)C4—C3—C2119.3 (3)
N2—Ni1—N6178.90 (8)C4—C3—H3120.3
N5—Ni1—N678.60 (7)C2—C3—H3120.3
N1—Ni1—O1155.50 (7)C3—C4—C5118.8 (3)
N1—Ni1—O292.80 (7)C3—C4—H4120.6
N2—Ni1—O176.40 (7)C5—C4—H4120.6
N2—Ni1—O2103.45 (7)N1—C5—C4121.8 (2)
N5—Ni1—O196.33 (6)N1—C5—C6115.6 (2)
N5—Ni1—O2155.21 (7)C4—C5—C6122.6 (2)
N6—Ni1—O1102.52 (7)N2—C6—C5116.0 (2)
N6—Ni1—O276.75 (7)N2—C6—H6122.0
O1—Ni1—O291.49 (6)C5—C6—H6122.0
C7—O1—Ni1110.40 (14)O1—C7—N4120.5 (2)
C14—O2—Ni1109.96 (14)O1—C7—N3125.0 (2)
C1—N1—C5118.5 (2)N4—C7—N3114.5 (2)
C1—N1—Ni1129.86 (18)N5—C8—C9123.1 (2)
C5—N1—Ni1111.68 (15)N5—C8—H8118.4
C6—N2—N3122.28 (19)C9—C8—H8118.4
C6—N2—Ni1117.53 (15)C8—C9—C10118.5 (2)
N3—N2—Ni1120.16 (14)C8—C9—H9120.8
N2—N3—C7107.89 (18)C10—C9—H9120.8
C7—N4—H4A123.4 (18)C11—C10—C9119.3 (2)
C7—N4—H4B118.4 (18)C11—C10—H10120.3
H4A—N4—H4B118 (3)C9—C10—H10120.3
C8—N5—C12118.0 (2)C10—C11—C12119.0 (2)
C8—N5—Ni1130.86 (17)C10—C11—H11120.5
C12—N5—Ni1110.72 (14)C12—C11—H11120.5
C13—N6—N7121.50 (19)N5—C12—C11121.9 (2)
C13—N6—Ni1118.89 (16)N5—C12—C13116.1 (2)
N7—N6—Ni1119.61 (14)C11—C12—C13121.9 (2)
N6—N7—C14108.16 (18)N6—C13—C12115.6 (2)
C14—N8—H8B116 (2)N6—C13—H13122.2
C14—N8—H8A116 (2)C12—C13—H13122.2
H8B—N8—H8A120 (3)O2—C14—N8120.3 (2)
N1—C1—C2123.0 (3)O2—C14—N7125.4 (2)
N1—C1—H1118.5N8—C14—N7114.2 (2)
C2—C1—H1118.5
N6—Ni1—O1—C7178.66 (15)N5—Ni1—N6—C132.48 (18)
N2—Ni1—O1—C71.57 (14)N2—Ni1—N6—N7100 (4)
O2—Ni1—O1—C7101.91 (14)O1—Ni1—N6—N788.36 (17)
N1—Ni1—O1—C71.8 (2)O2—Ni1—N6—N70.21 (16)
N5—Ni1—O1—C7101.66 (15)N1—Ni1—N6—N790.30 (17)
N6—Ni1—O2—C141.40 (15)N5—Ni1—N6—N7177.61 (18)
N2—Ni1—O2—C14179.71 (15)C13—N6—N7—C14178.4 (2)
O1—Ni1—O2—C14103.92 (15)Ni1—N6—N7—C141.6 (2)
N1—Ni1—O2—C14100.21 (15)C5—N1—C1—C20.6 (4)
N5—Ni1—O2—C144.7 (2)Ni1—N1—C1—C2178.7 (2)
N6—Ni1—N1—C11.7 (2)N1—C1—C2—C31.1 (5)
N2—Ni1—N1—C1178.5 (2)C1—C2—C3—C41.5 (6)
O1—Ni1—N1—C1175.1 (2)C2—C3—C4—C51.4 (5)
O2—Ni1—N1—C175.3 (2)C1—N1—C5—C40.4 (4)
N5—Ni1—N1—C180.0 (2)Ni1—N1—C5—C4179.0 (2)
N6—Ni1—N1—C5177.63 (15)C1—N1—C5—C6179.4 (2)
N2—Ni1—N1—C52.16 (15)Ni1—N1—C5—C61.2 (3)
O1—Ni1—N1—C55.5 (3)C3—C4—C5—N10.8 (4)
O2—Ni1—N1—C5105.32 (16)C3—C4—C5—C6179.0 (3)
N5—Ni1—N1—C599.34 (16)N3—N2—C6—C5178.7 (2)
N6—Ni1—N2—C6166 (4)Ni1—N2—C6—C53.3 (3)
O1—Ni1—N2—C6178.43 (18)N1—C5—C6—N21.2 (3)
O2—Ni1—N2—C693.31 (17)C4—C5—C6—N2178.6 (2)
N1—Ni1—N2—C63.01 (17)Ni1—O1—C7—N4176.06 (19)
N5—Ni1—N2—C684.56 (18)Ni1—O1—C7—N33.6 (3)
N6—Ni1—N2—N312 (4)N2—N3—C7—O13.8 (3)
O1—Ni1—N2—N30.36 (15)N2—N3—C7—N4175.9 (2)
O2—Ni1—N2—N388.62 (17)C12—N5—C8—C91.0 (4)
N1—Ni1—N2—N3178.92 (17)Ni1—N5—C8—C9173.06 (19)
N5—Ni1—N2—N393.51 (17)N5—C8—C9—C100.0 (4)
C6—N2—N3—C7180.0 (2)C8—C9—C10—C110.2 (4)
Ni1—N2—N3—C72.0 (2)C9—C10—C11—C121.3 (4)
N6—Ni1—N5—C8171.8 (2)C8—N5—C12—C112.2 (3)
N2—Ni1—N5—C89.4 (2)Ni1—N5—C12—C11175.77 (19)
O1—Ni1—N5—C886.7 (2)C8—N5—C12—C13174.4 (2)
O2—Ni1—N5—C8165.70 (18)Ni1—N5—C12—C130.8 (2)
N1—Ni1—N5—C869.5 (2)C10—C11—C12—N52.4 (4)
N6—Ni1—N5—C120.75 (15)C10—C11—C12—C13174.0 (2)
N2—Ni1—N5—C12178.14 (15)N7—N6—C13—C12176.4 (2)
O1—Ni1—N5—C12100.80 (15)Ni1—N6—C13—C123.7 (3)
O2—Ni1—N5—C126.8 (3)N5—C12—C13—N62.9 (3)
N1—Ni1—N5—C12102.99 (15)C11—C12—C13—N6173.7 (2)
N2—Ni1—N6—C1380 (4)Ni1—O2—C14—N8174.5 (2)
O1—Ni1—N6—C1391.55 (19)Ni1—O2—C14—N73.2 (3)
O2—Ni1—N6—C13179.88 (19)N6—N7—C14—O23.3 (3)
N1—Ni1—N6—C1389.79 (19)N6—N7—C14—N8174.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4B···N7i0.88 (2)2.09 (2)2.959 (3)170
N8—H8A···N3ii0.88 (2)2.12 (2)2.993 (3)171
C4—H4···O1iii0.952.463.152 (3)128
C9—H9···O1iv0.942.593.487 (3)156
C13—H13···O2v0.952.263.150 (3)154
Symmetry codes: (i) y, x, z+1/4; (ii) y, x, z1/4; (iii) y+1, x+1, z+1/4; (iv) x+1, y, z; (v) y+1, x, z1/4.
 

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