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The title compound, [Ni(C15H17N2O)(N3)], is a mononuclear nickel(II) complex. The NiII atom is four-coordinated by two N atoms and one O atom of the Schiff base ligand, and another N atom from an azide anion, forming a slightly distorted square-planar coordination configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001881/su6160sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001881/su6160Isup2.hkl
Contains datablock I

CCDC reference: 263585

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.121
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.15 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 0 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 (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

Azido[1-(isobutylaminomethyliminomethyl)-2-naphtholato]nickel(II) top
Crystal data top
[Ni(C15H17N2O)(N3)]F(000) = 1424
Mr = 342.05Dx = 1.488 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 7800 reflections
a = 7.576 (1) Åθ = 2.7–27.5°
b = 13.300 (2) ŵ = 1.28 mm1
c = 30.306 (2) ÅT = 298 K
V = 3053.7 (6) Å3Block, green
Z = 80.29 × 0.12 × 0.10 mm
Data collection top
Bruker APEX area-detector
diffractometer
3488 independent reflections
Radiation source: fine-focus sealed tube2859 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.708, Tmax = 0.883k = 1616
24371 measured reflectionsl = 3939
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0564P)2 + 2.2975P]
where P = (Fo2 + 2Fc2)/3
3488 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.97 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
Ni10.60659 (5)0.45725 (2)0.612031 (11)0.04363 (14)
O10.5695 (3)0.54969 (12)0.65520 (6)0.0466 (4)
N10.7007 (3)0.36348 (14)0.64986 (7)0.0429 (5)
N20.6465 (4)0.35972 (19)0.56495 (8)0.0605 (7)
N30.5198 (4)0.55043 (19)0.56976 (9)0.0671 (8)
N40.4163 (4)0.61455 (18)0.57709 (7)0.0542 (6)
N50.3196 (5)0.6792 (2)0.58174 (10)0.0843 (10)
C10.7959 (5)0.3942 (4)0.53841 (15)0.0968 (14)
H1A0.81540.34810.51450.145*
H1B0.89970.39740.55650.145*
H1C0.77070.45970.52670.145*
C20.4960 (6)0.3439 (3)0.53510 (12)0.0769 (10)
H2A0.47000.40540.51990.115*
H2B0.39490.32340.55190.115*
H2C0.52500.29260.51400.115*
C30.6747 (6)0.2596 (3)0.58726 (13)0.0787 (10)
H3A0.56170.22910.59410.094*
H3B0.73860.21480.56770.094*
C40.7751 (5)0.2751 (2)0.62768 (11)0.0616 (8)
H4A0.89860.28630.62080.074*
H4B0.76610.21650.64660.074*
C50.7124 (3)0.36995 (18)0.69229 (9)0.0421 (5)
H50.76730.31700.70690.051*
C60.6494 (3)0.45042 (16)0.71866 (9)0.0386 (5)
C70.5805 (3)0.53657 (17)0.69782 (9)0.0400 (5)
C80.5189 (3)0.61777 (19)0.72460 (9)0.0463 (6)
H80.47350.67500.71110.056*
C90.5252 (4)0.6129 (2)0.76883 (10)0.0497 (6)
H90.48350.66710.78520.060*
C100.5935 (3)0.5276 (2)0.79150 (10)0.0465 (6)
C110.6001 (4)0.5233 (3)0.83810 (11)0.0591 (8)
H110.55970.57770.85450.071*
C120.6646 (5)0.4407 (3)0.85934 (11)0.0665 (9)
H120.66880.43880.89000.080*
C130.7236 (4)0.3599 (3)0.83498 (10)0.0618 (8)
H130.76740.30360.84950.074*
C140.7194 (4)0.3608 (2)0.78976 (9)0.0503 (6)
H140.75950.30490.77420.060*
C150.6551 (3)0.44500 (18)0.76629 (9)0.0418 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0501 (2)0.0332 (2)0.0476 (2)0.00406 (13)0.00118 (14)0.00136 (13)
O10.0575 (11)0.0296 (8)0.0527 (11)0.0051 (7)0.0011 (8)0.0029 (7)
N10.0445 (12)0.0307 (10)0.0534 (12)0.0041 (8)0.0008 (9)0.0013 (9)
N20.0790 (18)0.0499 (14)0.0528 (14)0.0126 (13)0.0049 (13)0.0057 (11)
N30.095 (2)0.0549 (15)0.0514 (14)0.0248 (15)0.0025 (14)0.0088 (11)
N40.0746 (17)0.0462 (13)0.0419 (12)0.0049 (12)0.0098 (11)0.0031 (10)
N50.106 (2)0.0742 (19)0.0727 (19)0.0413 (19)0.0108 (17)0.0027 (16)
C10.077 (3)0.113 (3)0.101 (3)0.005 (2)0.022 (2)0.039 (3)
C20.101 (3)0.067 (2)0.063 (2)0.016 (2)0.0063 (19)0.0068 (16)
C30.106 (3)0.0514 (18)0.078 (2)0.0151 (19)0.010 (2)0.0095 (17)
C40.077 (2)0.0414 (14)0.0666 (18)0.0185 (14)0.0023 (16)0.0088 (13)
C50.0385 (13)0.0318 (11)0.0562 (15)0.0012 (10)0.0049 (11)0.0058 (10)
C60.0314 (11)0.0303 (11)0.0542 (14)0.0037 (9)0.0005 (10)0.0003 (10)
C70.0344 (12)0.0314 (12)0.0543 (14)0.0049 (9)0.0000 (10)0.0003 (10)
C80.0437 (14)0.0335 (12)0.0618 (17)0.0009 (10)0.0023 (12)0.0019 (11)
C90.0429 (14)0.0410 (14)0.0652 (17)0.0024 (11)0.0071 (12)0.0118 (12)
C100.0374 (13)0.0479 (14)0.0542 (15)0.0108 (11)0.0007 (11)0.0046 (12)
C110.0530 (17)0.0687 (19)0.0556 (17)0.0132 (14)0.0041 (13)0.0094 (15)
C120.0592 (18)0.088 (2)0.0518 (17)0.0188 (18)0.0028 (14)0.0064 (16)
C130.0571 (18)0.0666 (19)0.0616 (18)0.0114 (15)0.0084 (14)0.0173 (15)
C140.0465 (15)0.0458 (14)0.0586 (16)0.0079 (12)0.0038 (12)0.0068 (12)
C150.0315 (12)0.0408 (13)0.0530 (14)0.0106 (10)0.0021 (10)0.0024 (11)
Geometric parameters (Å, º) top
Ni1—O11.817 (2)C4—H4A0.9700
Ni1—N11.838 (2)C4—H4B0.9700
Ni1—N31.900 (3)C5—C61.419 (3)
Ni1—N21.952 (2)C5—H50.9300
O1—C71.306 (3)C6—C71.409 (3)
N1—C51.292 (3)C6—C151.446 (4)
N1—C41.467 (3)C7—C81.429 (3)
N2—C11.462 (5)C8—C91.343 (4)
N2—C21.470 (4)C8—H80.9300
N2—C31.508 (4)C9—C101.425 (4)
N3—N41.180 (3)C9—H90.9300
N4—N51.139 (4)C10—C111.414 (4)
C1—H1A0.9600C10—C151.417 (4)
C1—H1B0.9600C11—C121.365 (5)
C1—H1C0.9600C11—H110.9300
C2—H2A0.9600C12—C131.378 (5)
C2—H2B0.9600C12—H120.9300
C2—H2C0.9600C13—C141.371 (4)
C3—C41.456 (5)C13—H130.9300
C3—H3A0.9700C14—C151.413 (4)
C3—H3B0.9700C14—H140.9300
O1—Ni1—N194.0 (1)N1—C4—H4A110.2
O1—Ni1—N389.5 (1)C3—C4—H4B110.2
N1—Ni1—N3176.0 (1)N1—C4—H4B110.2
O1—Ni1—N2179.1 (1)H4A—C4—H4B108.5
N1—Ni1—N286.8 (1)N1—C5—C6126.0 (2)
N3—Ni1—N289.7 (1)N1—C5—H5117.0
C7—O1—Ni1127.7 (2)C6—C5—H5117.0
C5—N1—C4118.9 (2)C7—C6—C5119.1 (2)
C5—N1—Ni1127.05 (17)C7—C6—C15119.9 (2)
C4—N1—Ni1114.01 (19)C5—C6—C15121.0 (2)
C1—N2—C2107.9 (3)O1—C7—C6125.2 (2)
C1—N2—C3114.4 (3)O1—C7—C8116.1 (2)
C2—N2—C3105.0 (3)C6—C7—C8118.8 (2)
C1—N2—Ni1108.3 (2)C9—C8—C7121.3 (3)
C2—N2—Ni1115.1 (2)C9—C8—H8119.4
C3—N2—Ni1106.3 (2)C7—C8—H8119.4
N4—N3—Ni1125.1 (2)C8—C9—C10122.2 (3)
N5—N4—N3175.7 (3)C8—C9—H9118.9
N2—C1—H1A109.5C10—C9—H9118.9
N2—C1—H1B109.5C11—C10—C15119.7 (3)
H1A—C1—H1B109.5C11—C10—C9121.7 (3)
N2—C1—H1C109.5C15—C10—C9118.5 (3)
H1A—C1—H1C109.5C12—C11—C10121.0 (3)
H1B—C1—H1C109.5C12—C11—H11119.5
N2—C2—H2A109.5C10—C11—H11119.5
N2—C2—H2B109.5C11—C12—C13119.4 (3)
H2A—C2—H2B109.5C11—C12—H12120.3
N2—C2—H2C109.5C13—C12—H12120.3
H2A—C2—H2C109.5C14—C13—C12121.5 (3)
H2B—C2—H2C109.5C14—C13—H13119.3
C4—C3—N2109.0 (3)C12—C13—H13119.3
C4—C3—H3A109.9C13—C14—C15121.2 (3)
N2—C3—H3A109.9C13—C14—H14119.4
C4—C3—H3B109.9C15—C14—H14119.4
N2—C3—H3B109.9C14—C15—C10117.1 (3)
H3A—C3—H3B108.3C14—C15—C6123.5 (2)
C3—C4—N1107.3 (3)C10—C15—C6119.3 (2)
C3—C4—H4A110.2
N1—Ni1—O1—C710.8 (2)Ni1—O1—C7—C8170.89 (17)
N3—Ni1—O1—C7171.3 (2)C5—C6—C7—O10.2 (4)
O1—Ni1—N1—C55.0 (2)C15—C6—C7—O1179.8 (2)
N2—Ni1—N1—C5175.4 (2)C5—C6—C7—C8179.4 (2)
O1—Ni1—N1—C4172.3 (2)C15—C6—C7—C80.6 (3)
N2—Ni1—N1—C47.3 (2)O1—C7—C8—C9179.5 (2)
N1—Ni1—N2—C1106.7 (3)C6—C7—C8—C90.2 (4)
N3—Ni1—N2—C171.2 (3)C7—C8—C9—C100.2 (4)
N1—Ni1—N2—C2132.5 (2)C8—C9—C10—C11179.8 (3)
N3—Ni1—N2—C249.6 (2)C8—C9—C10—C150.6 (4)
N1—Ni1—N2—C316.7 (2)C15—C10—C11—C120.1 (4)
N3—Ni1—N2—C3165.4 (3)C9—C10—C11—C12179.5 (3)
O1—Ni1—N3—N428.1 (3)C10—C11—C12—C130.3 (5)
N2—Ni1—N3—N4152.3 (3)C11—C12—C13—C140.1 (5)
C1—N2—C3—C481.9 (4)C12—C13—C14—C150.4 (5)
C2—N2—C3—C4160.0 (3)C13—C14—C15—C100.8 (4)
Ni1—N2—C3—C437.5 (4)C13—C14—C15—C6179.3 (3)
N2—C3—C4—N143.6 (4)C11—C10—C15—C140.6 (4)
C5—N1—C4—C3152.1 (3)C9—C10—C15—C14179.0 (2)
Ni1—N1—C4—C330.4 (3)C11—C10—C15—C6179.4 (2)
C4—N1—C5—C6179.3 (3)C9—C10—C15—C61.0 (3)
Ni1—N1—C5—C62.1 (4)C7—C6—C15—C14178.9 (2)
N1—C5—C6—C76.0 (4)C5—C6—C15—C141.1 (4)
N1—C5—C6—C15174.0 (2)C7—C6—C15—C101.0 (3)
Ni1—O1—C7—C69.9 (4)C5—C6—C15—C10179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1C···N30.962.603.098 (5)112
C2—H2A···N30.962.482.946 (5)110
C4—H4B···O1i0.972.563.327 (3)136
Symmetry code: (i) x+3/2, y1/2, z.
 

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