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In the title compound, [(C7H5O2)2(C5H6N2)2Ni], the NiII atom is six coordinated by four O atoms from two benzoate anions, and two pyridine N atoms from the two 2-amino­pyridine ligands to give a distorted octahedral geometry. All of the O atoms and both the amine groups of the ligands contribute to form a one-dimensional chain consisting of intra- and intermolecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019329/lh6101sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019329/lh6101Isup2.hkl
Contains datablock I

CCDC reference: 225650

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.095
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

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Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ni1 - O1 = 10.02 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ni1 - O3 = 12.95 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.66 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O2 = 6.93 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O4 = 6.75 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - C1 = 6.67 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - C8 = 5.55 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C4
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

dibenzoato-di(2-aminopyridine)nickel(II) top
Crystal data top
[Ni(C7H5O2)2(C5H6N2)2]F(000) = 2032
Mr = 489.17Dx = 1.373 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 19350 reflections
a = 25.097 (5) Åθ = 2.9–25.4°
b = 10.991 (2) ŵ = 0.86 mm1
c = 17.499 (3) ÅT = 293 K
β = 101.28 (3)°Prism, blue
V = 4733.7 (15) Å30.55 × 0.43 × 0.38 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
5137 independent reflections
Radiation source: fine-focus sealed tube4599 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1432
Tmin = 0.649, Tmax = 0.722k = 1313
19355 measured reflectionsl = 2220
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0623P)2 + 1.3806P]
where P = (Fo2 + 2Fc2)/3
5137 reflections(Δ/σ)max = 0.011
299 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.31 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*/Ueq
Ni10.120153 (7)0.138617 (16)0.006830 (11)0.04395 (9)
O10.13393 (5)0.29257 (10)0.06805 (7)0.0533 (3)
O20.09143 (5)0.13187 (9)0.09891 (8)0.0547 (3)
O30.19061 (4)0.03698 (9)0.05237 (7)0.0505 (3)
O40.11892 (4)0.04916 (10)0.01732 (6)0.0519 (3)
N10.04671 (6)0.19525 (13)0.07201 (9)0.0571 (3)
N20.00972 (6)0.00270 (16)0.09137 (11)0.0757 (5)
H2A0.01770.04700.11250.080*
H2B0.04070.02860.06360.080*
N30.15778 (5)0.17196 (12)0.09912 (8)0.0478 (3)
N40.20348 (6)0.34509 (13)0.04598 (9)0.0584 (4)
H4B0.22740.40550.04780.080*
H4C0.18520.34180.00660.080*
C10.11146 (6)0.23599 (13)0.11642 (9)0.0482 (3)
C20.10890 (7)0.29026 (14)0.19359 (9)0.0511 (4)
C30.08226 (10)0.2292 (2)0.24451 (12)0.0753 (5)
H3A0.06540.15220.22950.080*
C40.08069 (13)0.2793 (3)0.31658 (14)0.0974 (8)
H4A0.06240.23720.35210.080*
C50.10481 (12)0.3890 (2)0.33736 (13)0.0883 (7)
H5A0.10270.42440.38680.080*
C60.13156 (11)0.44945 (19)0.28825 (12)0.0822 (7)
H6A0.14900.52570.30380.080*
C70.13421 (9)0.39987 (17)0.21640 (11)0.0667 (5)
H7A0.15330.44190.18180.080*
C80.16455 (6)0.05814 (13)0.02828 (8)0.0440 (3)
C90.18662 (6)0.18095 (13)0.05278 (8)0.0449 (3)
C100.15254 (8)0.28150 (15)0.03900 (10)0.0552 (4)
H10A0.11520.27140.01420.080*
C110.17245 (10)0.39622 (17)0.06087 (12)0.0692 (5)
H11A0.14890.46570.05130.080*
C120.22616 (10)0.41067 (18)0.09612 (11)0.0698 (5)
H12A0.23990.49030.11150.080*
C130.26012 (8)0.31148 (18)0.10973 (10)0.0629 (5)
H13A0.29760.32230.13390.080*
C140.24040 (7)0.19605 (15)0.08848 (9)0.0516 (4)
H14A0.26390.12660.09850.080*
C150.00464 (7)0.12335 (18)0.10161 (11)0.0586 (4)
C160.04366 (9)0.1722 (3)0.14468 (15)0.0887 (7)
H16A0.07370.11990.16530.080*
C170.04756 (11)0.2930 (3)0.15845 (19)0.1132 (10)
H17A0.08100.32750.18590.080*
C180.00416 (12)0.3669 (2)0.1293 (2)0.1170 (12)
H18A0.00550.45220.14120.080*
C190.04143 (10)0.3152 (2)0.08709 (17)0.0904 (8)
H19A0.07150.36730.06630.080*
C200.19480 (6)0.25976 (14)0.10235 (9)0.0491 (3)
C210.22309 (8)0.26359 (19)0.16393 (11)0.0663 (5)
H21A0.25040.32450.16430.080*
C220.21141 (9)0.1814 (2)0.22263 (12)0.0741 (5)
H22A0.23060.18410.26500.080*
C230.17159 (9)0.0936 (2)0.22153 (11)0.0691 (5)
H23A0.16230.03550.26300.080*
C240.14652 (7)0.09197 (17)0.15928 (10)0.0583 (4)
H24A0.11920.03150.15740.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.04102 (13)0.03469 (13)0.05502 (14)0.00833 (7)0.00664 (9)0.00090 (7)
O10.0583 (6)0.0423 (5)0.0612 (6)0.0127 (5)0.0164 (5)0.0022 (5)
O20.0542 (7)0.0437 (6)0.0687 (7)0.0158 (5)0.0181 (6)0.0068 (5)
O30.0483 (6)0.0407 (5)0.0614 (6)0.0089 (4)0.0079 (5)0.0026 (4)
O40.0505 (6)0.0386 (6)0.0621 (6)0.0062 (4)0.0004 (5)0.0002 (4)
N10.0441 (7)0.0533 (8)0.0714 (9)0.0036 (6)0.0047 (6)0.0072 (6)
N20.0504 (8)0.0687 (10)0.1000 (12)0.0209 (8)0.0047 (8)0.0016 (9)
N30.0444 (7)0.0452 (6)0.0522 (7)0.0027 (5)0.0051 (5)0.0039 (5)
N40.0566 (8)0.0484 (7)0.0725 (9)0.0163 (6)0.0181 (7)0.0001 (6)
C10.0417 (7)0.0408 (7)0.0616 (9)0.0049 (6)0.0088 (6)0.0003 (6)
C20.0503 (8)0.0451 (8)0.0565 (9)0.0011 (6)0.0067 (7)0.0002 (6)
C30.0903 (15)0.0683 (12)0.0727 (12)0.0188 (11)0.0290 (11)0.0053 (10)
C40.131 (2)0.0986 (18)0.0720 (13)0.0149 (16)0.0429 (15)0.0013 (13)
C50.125 (2)0.0805 (14)0.0587 (11)0.0147 (15)0.0159 (13)0.0096 (11)
C60.1137 (18)0.0551 (11)0.0703 (12)0.0022 (11)0.0008 (12)0.0122 (9)
C70.0832 (13)0.0495 (9)0.0647 (10)0.0104 (9)0.0080 (9)0.0024 (8)
C80.0467 (8)0.0401 (7)0.0461 (7)0.0062 (6)0.0117 (6)0.0003 (5)
C90.0543 (8)0.0419 (7)0.0403 (7)0.0015 (6)0.0137 (6)0.0007 (6)
C100.0629 (10)0.0435 (8)0.0594 (9)0.0041 (7)0.0120 (7)0.0029 (7)
C110.0938 (15)0.0407 (8)0.0753 (12)0.0029 (9)0.0216 (11)0.0055 (8)
C120.0977 (15)0.0508 (10)0.0627 (10)0.0191 (10)0.0200 (10)0.0112 (8)
C130.0655 (11)0.0709 (12)0.0528 (9)0.0176 (9)0.0128 (8)0.0079 (8)
C140.0569 (9)0.0544 (9)0.0447 (7)0.0005 (7)0.0127 (6)0.0013 (6)
C150.0423 (9)0.0735 (12)0.0595 (9)0.0065 (7)0.0086 (7)0.0012 (8)
C160.0472 (11)0.1073 (18)0.1021 (17)0.0040 (11)0.0085 (11)0.0091 (14)
C170.0655 (15)0.123 (2)0.138 (2)0.0194 (15)0.0120 (15)0.036 (2)
C180.0830 (18)0.0787 (17)0.176 (3)0.0142 (13)0.0063 (19)0.0430 (18)
C190.0675 (13)0.0611 (12)0.132 (2)0.0027 (10)0.0054 (13)0.0216 (13)
C200.0441 (8)0.0470 (8)0.0546 (8)0.0018 (6)0.0056 (6)0.0130 (6)
C210.0640 (11)0.0726 (12)0.0653 (10)0.0049 (9)0.0197 (8)0.0167 (9)
C220.0778 (13)0.0920 (14)0.0561 (10)0.0074 (12)0.0222 (9)0.0142 (10)
C230.0741 (12)0.0797 (12)0.0492 (9)0.0100 (10)0.0016 (8)0.0033 (9)
C240.0573 (10)0.0582 (10)0.0557 (9)0.0018 (8)0.0017 (7)0.0031 (7)
Geometric parameters (Å, º) top
Ni1—N32.0569 (14)C6—H6A0.9600
Ni1—N12.0647 (15)C7—H7A0.9600
Ni1—O42.0716 (12)C8—C91.490 (2)
Ni1—O22.1144 (14)C9—C141.382 (2)
Ni1—O12.1266 (11)C9—C101.389 (2)
Ni1—O32.1750 (12)C10—C111.382 (2)
O1—C11.2681 (19)C10—H10A0.9601
O2—C11.2632 (18)C11—C121.377 (3)
O3—C81.2611 (17)C11—H11A0.9600
O4—C81.2651 (18)C12—C131.376 (3)
N1—C151.339 (2)C12—H12A0.9600
N1—C191.345 (3)C13—C141.386 (2)
N2—C151.341 (3)C13—H13A0.9600
N2—H2A0.9000C14—H14A0.9599
N2—H2B0.9000C15—C161.403 (3)
N3—C201.348 (2)C16—C171.350 (4)
N3—C241.358 (2)C16—H16A0.9599
N4—C201.348 (2)C17—C181.374 (4)
N4—H4B0.9001C17—H17A0.9599
N4—H4C0.8999C18—C191.359 (4)
C1—C21.489 (2)C18—H18A0.9600
C2—C71.384 (2)C19—H19A0.9600
C2—C31.387 (3)C20—C211.402 (2)
C3—C41.384 (3)C21—C221.356 (3)
C3—H3A0.9599C21—H21A0.9601
C4—C51.366 (4)C22—C231.392 (3)
C4—H4A0.9599C22—H22A0.9600
C5—C61.363 (4)C23—C241.360 (3)
C5—H5A0.9601C23—H23A0.9600
C6—C71.384 (3)C24—H24A0.9600
N3—Ni1—N190.56 (6)O3—C8—O4119.50 (14)
N3—Ni1—O496.27 (5)O3—C8—C9121.03 (14)
N1—Ni1—O4104.78 (5)O4—C8—C9119.47 (12)
N3—Ni1—O2168.76 (5)C14—C9—C10119.78 (15)
N1—Ni1—O294.23 (6)C14—C9—C8120.94 (14)
O4—Ni1—O292.34 (4)C10—C9—C8119.28 (14)
N3—Ni1—O1107.32 (5)C11—C10—C9120.03 (18)
N1—Ni1—O196.92 (6)C11—C10—H10A120.0
O4—Ni1—O1147.68 (4)C9—C10—H10A120.0
O2—Ni1—O162.02 (4)C12—C11—C10119.89 (19)
N3—Ni1—O390.58 (5)C12—C11—H11A120.1
N1—Ni1—O3166.56 (5)C10—C11—H11A120.0
O4—Ni1—O361.79 (4)C13—C12—C11120.33 (17)
O2—Ni1—O387.12 (5)C13—C12—H12A119.8
O1—Ni1—O395.52 (5)C11—C12—H12A119.8
C1—O1—Ni188.92 (9)C12—C13—C14120.16 (18)
C1—O2—Ni189.60 (10)C12—C13—H13A119.9
C8—O3—Ni186.93 (9)C14—C13—H13A119.9
C8—O4—Ni191.48 (8)C9—C14—C13119.81 (16)
C15—N1—C19117.52 (17)C9—C14—H14A119.9
C15—N1—Ni1125.93 (13)C13—C14—H14A120.2
C19—N1—Ni1116.53 (13)N1—C15—N2118.99 (17)
C15—N2—H2A120.0N1—C15—C16121.0 (2)
C15—N2—H2B120.0N2—C15—C16119.97 (19)
H2A—N2—H2B120.0C17—C16—C15119.8 (2)
C20—N3—C24118.12 (15)C17—C16—H16A119.8
C20—N3—Ni1125.90 (11)C15—C16—H16A120.3
C24—N3—Ni1115.81 (11)C16—C17—C18119.4 (2)
C20—N4—H4B120.1C16—C17—H17A120.2
C20—N4—H4C119.9C18—C17—H17A120.3
H4B—N4—H4C120.0C19—C18—C17118.5 (2)
O2—C1—O1119.35 (15)C19—C18—H18A121.1
O2—C1—C2119.81 (14)C17—C18—H18A120.3
O1—C1—C2120.83 (14)N1—C19—C18123.8 (2)
C7—C2—C3119.18 (17)N1—C19—H19A118.1
C7—C2—C1120.76 (16)C18—C19—H19A118.1
C3—C2—C1120.03 (15)N4—C20—N3118.78 (15)
C4—C3—C2119.7 (2)N4—C20—C21120.53 (16)
C4—C3—H3A120.7N3—C20—C21120.68 (16)
C2—C3—H3A119.6C22—C21—C20119.69 (18)
C5—C4—C3120.3 (2)C22—C21—H21A120.5
C5—C4—H4A119.8C20—C21—H21A119.8
C3—C4—H4A120.0C21—C22—C23120.05 (18)
C6—C5—C4120.6 (2)C21—C22—H22A119.9
C6—C5—H5A119.5C23—C22—H22A120.1
C4—C5—H5A119.9C24—C23—C22117.75 (19)
C5—C6—C7119.9 (2)C24—C23—H23A120.9
C5—C6—H6A120.0C22—C23—H23A121.3
C7—C6—H6A120.1N3—C24—C23123.61 (18)
C6—C7—C2120.3 (2)N3—C24—H24A117.6
C6—C7—H7A120.1C23—C24—H24A118.8
C2—C7—H7A119.6
N3—Ni1—O1—C1174.16 (9)O1—C1—C2—C3177.42 (17)
N1—Ni1—O1—C193.08 (10)C7—C2—C3—C40.9 (3)
O4—Ni1—O1—C139.17 (13)C1—C2—C3—C4179.1 (2)
O2—Ni1—O1—C11.95 (9)C2—C3—C4—C50.6 (4)
O3—Ni1—O1—C181.81 (9)C3—C4—C5—C61.2 (4)
N3—Ni1—O2—C117.4 (3)C4—C5—C6—C70.3 (4)
N1—Ni1—O2—C197.56 (10)C5—C6—C7—C21.2 (3)
O4—Ni1—O2—C1157.43 (9)C3—C2—C7—C61.8 (3)
O1—Ni1—O2—C11.96 (9)C1—C2—C7—C6179.99 (18)
O3—Ni1—O2—C195.84 (10)Ni1—O3—C8—O45.32 (14)
C8—Ni1—O2—C1126.72 (10)Ni1—O3—C8—C9174.59 (13)
N3—Ni1—O3—C8100.01 (9)Ni1—O4—C8—O35.58 (15)
N1—Ni1—O3—C85.1 (3)Ni1—O4—C8—C9174.33 (12)
O4—Ni1—O3—C83.20 (8)O3—C8—C9—C1413.9 (2)
O2—Ni1—O3—C891.00 (9)O4—C8—C9—C14166.21 (14)
O1—Ni1—O3—C8152.53 (9)O3—C8—C9—C10166.46 (15)
N3—Ni1—O4—C890.48 (9)O4—C8—C9—C1013.4 (2)
N1—Ni1—O4—C8177.28 (9)C14—C9—C10—C110.1 (2)
O2—Ni1—O4—C882.28 (10)C8—C9—C10—C11179.55 (15)
O1—Ni1—O4—C846.73 (13)C9—C10—C11—C120.2 (3)
O3—Ni1—O4—C83.19 (8)C10—C11—C12—C130.0 (3)
N3—Ni1—N1—C15107.54 (16)C11—C12—C13—C140.4 (3)
O4—Ni1—N1—C1510.91 (17)C10—C9—C14—C130.5 (2)
O2—Ni1—N1—C1582.63 (16)C8—C9—C14—C13179.10 (14)
O1—Ni1—N1—C15144.93 (15)C12—C13—C14—C90.7 (3)
O3—Ni1—N1—C1512.7 (3)C19—N1—C15—N2176.3 (2)
N3—Ni1—N1—C1971.08 (19)Ni1—N1—C15—N22.3 (3)
O4—Ni1—N1—C19167.71 (18)C19—N1—C15—C161.9 (3)
O2—Ni1—N1—C1998.75 (18)Ni1—N1—C15—C16179.50 (17)
O1—Ni1—N1—C1936.45 (19)N1—C15—C16—C171.7 (4)
O3—Ni1—N1—C19165.9 (2)N2—C15—C16—C17176.4 (3)
N1—Ni1—N3—C20111.99 (13)C15—C16—C17—C180.6 (5)
O4—Ni1—N3—C20143.08 (12)C16—C17—C18—C190.3 (6)
O2—Ni1—N3—C203.3 (3)C15—N1—C19—C181.0 (4)
O1—Ni1—N3—C2014.56 (14)Ni1—N1—C19—C18179.8 (3)
O3—Ni1—N3—C2081.40 (13)C17—C18—C19—N10.1 (5)
N1—Ni1—N3—C2472.86 (12)C24—N3—C20—N4175.18 (15)
O4—Ni1—N3—C2432.07 (12)Ni1—N3—C20—N49.8 (2)
O2—Ni1—N3—C24171.8 (2)C24—N3—C20—C213.7 (2)
O1—Ni1—N3—C24170.29 (11)Ni1—N3—C20—C21171.34 (12)
O3—Ni1—N3—C2493.75 (12)N4—C20—C21—C22175.94 (17)
Ni1—O2—C1—O13.33 (15)N3—C20—C21—C222.9 (3)
Ni1—O2—C1—C2176.09 (13)C20—C21—C22—C230.2 (3)
Ni1—O1—C1—O23.32 (15)C21—C22—C23—C241.7 (3)
Ni1—O1—C1—C2176.10 (13)C20—N3—C24—C231.9 (3)
O2—C1—C2—C7174.98 (16)Ni1—N3—C24—C23173.69 (14)
O1—C1—C2—C74.4 (2)C22—C23—C24—N30.8 (3)
O2—C1—C2—C33.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.902.132.9187 (19)146
N2—H2B···O40.901.992.850 (2)161
N4—H4B···O3ii0.902.172.9790 (18)149
N4—H4C···O10.902.082.954 (2)164
Symmetry codes: (i) x, y, z; (ii) x+1/2, y+1/2, z.
 

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