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The title mononuclear nickel(II) complex, [Ni(C13H17Cl2N2O)(N3)], is isostructural with the copper(II) complex reported recently by Wei & Wang [Acta Cryst. (2006), E62, m309-m311]. The NiII ion is four-coordinate in a square-planar geometry defined by an imine N, an amine N, a phenolate O atom of the Schiff base and a terminal N atom of the azide anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006155/tk6310sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006155/tk6310Isup2.hkl
Contains datablock I

CCDC reference: 601259

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.086
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.67 Ratio 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 3 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 2 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 (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Azido{2,4-dichloro-6-[2-(diethylamino)ethyliminomethyl]phenolato}nickel(II) top
Crystal data top
[Ni(C13H17Cl2N2O)(N3)]F(000) = 800
Mr = 388.93Dx = 1.603 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3623 reflections
a = 16.361 (2) Åθ = 2.4–26.7°
b = 9.735 (1) ŵ = 1.54 mm1
c = 10.165 (1) ÅT = 298 K
β = 95.656 (1)°Block, green
V = 1611.1 (3) Å30.23 × 0.20 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3618 independent reflections
Radiation source: fine-focus sealed tube2772 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2021
Tmin = 0.718, Tmax = 0.836k = 1212
10944 measured reflectionsl = 1313
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0415P)2 + 0.2299P]
where P = (Fo2 + 2Fc2)/3
3618 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.21 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
Ni10.781189 (17)0.74170 (3)0.36977 (3)0.03613 (11)
Cl10.64843 (5)0.32091 (7)0.40895 (9)0.0727 (2)
Cl20.51042 (5)0.51430 (9)0.83131 (8)0.0757 (2)
O10.71146 (9)0.59716 (15)0.39241 (16)0.0439 (4)
N10.72481 (11)0.86201 (18)0.46892 (19)0.0378 (4)
N20.85538 (11)0.89562 (18)0.34168 (18)0.0383 (4)
N30.84241 (14)0.6270 (2)0.2652 (2)0.0539 (6)
N40.84617 (14)0.5060 (2)0.2778 (2)0.0556 (6)
N50.8518 (2)0.3890 (3)0.2825 (3)0.1009 (11)
C10.64261 (13)0.6942 (2)0.5695 (2)0.0398 (5)
C20.66291 (13)0.5859 (2)0.4865 (2)0.0391 (5)
C30.62803 (15)0.4564 (2)0.5119 (3)0.0474 (6)
C40.58140 (15)0.4342 (3)0.6143 (3)0.0534 (7)
H40.56040.34740.62880.064*
C50.56599 (15)0.5427 (3)0.6959 (3)0.0511 (6)
C60.59435 (14)0.6713 (3)0.6737 (3)0.0467 (6)
H60.58170.74380.72760.056*
C70.67289 (13)0.8309 (2)0.5510 (2)0.0389 (5)
H70.65360.90120.60160.047*
C80.74768 (14)1.0065 (2)0.4546 (3)0.0436 (6)
H8A0.73751.05830.53280.052*
H8B0.71621.04720.37850.052*
C90.83794 (14)1.0065 (2)0.4362 (2)0.0425 (6)
H9A0.85351.09480.40230.051*
H9B0.86980.99120.52060.051*
C100.94445 (15)0.8587 (3)0.3608 (2)0.0485 (6)
H10A0.97680.94230.36310.058*
H10B0.95810.80500.28560.058*
C110.96780 (17)0.7784 (3)0.4852 (3)0.0560 (7)
H11A0.95200.82880.55990.084*
H11B1.02610.76390.49520.084*
H11C0.94020.69130.47990.084*
C120.83209 (17)0.9409 (3)0.2016 (2)0.0529 (7)
H12A0.77530.97100.19430.063*
H12B0.83510.86180.14430.063*
C130.8835 (2)1.0549 (3)0.1503 (3)0.0803 (10)
H13A0.88221.13370.20680.120*
H13B0.86171.07910.06220.120*
H13C0.93921.02400.14940.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03865 (18)0.02987 (16)0.03992 (18)0.00279 (12)0.00419 (13)0.00290 (12)
Cl10.0799 (5)0.0336 (3)0.1050 (6)0.0051 (3)0.0104 (5)0.0107 (4)
Cl20.0642 (5)0.0869 (6)0.0790 (5)0.0178 (4)0.0226 (4)0.0201 (4)
O10.0454 (10)0.0309 (8)0.0562 (10)0.0060 (7)0.0086 (8)0.0064 (7)
N10.0338 (10)0.0284 (9)0.0510 (12)0.0011 (7)0.0034 (9)0.0015 (8)
N20.0419 (11)0.0373 (10)0.0360 (10)0.0076 (8)0.0051 (8)0.0016 (8)
N30.0653 (15)0.0452 (12)0.0543 (13)0.0048 (10)0.0211 (11)0.0115 (10)
N40.0722 (16)0.0519 (14)0.0443 (13)0.0080 (11)0.0132 (11)0.0106 (10)
N50.166 (3)0.0530 (16)0.090 (2)0.0291 (18)0.045 (2)0.0018 (16)
C10.0312 (12)0.0348 (11)0.0528 (14)0.0011 (9)0.0020 (11)0.0045 (11)
C20.0323 (12)0.0330 (11)0.0505 (14)0.0014 (9)0.0041 (10)0.0037 (10)
C30.0425 (14)0.0306 (12)0.0667 (17)0.0008 (10)0.0061 (12)0.0020 (11)
C40.0423 (14)0.0438 (14)0.0726 (18)0.0116 (11)0.0019 (13)0.0141 (13)
C50.0358 (14)0.0585 (16)0.0590 (16)0.0060 (11)0.0052 (12)0.0149 (13)
C60.0360 (13)0.0466 (14)0.0578 (16)0.0006 (11)0.0059 (12)0.0042 (12)
C70.0331 (12)0.0327 (11)0.0507 (14)0.0041 (9)0.0037 (10)0.0025 (10)
C80.0463 (14)0.0278 (11)0.0567 (15)0.0005 (10)0.0055 (12)0.0001 (10)
C90.0466 (14)0.0356 (12)0.0453 (13)0.0112 (10)0.0052 (11)0.0041 (10)
C100.0422 (14)0.0520 (14)0.0527 (15)0.0091 (11)0.0118 (12)0.0090 (12)
C110.0466 (16)0.0586 (16)0.0619 (18)0.0035 (12)0.0003 (13)0.0068 (13)
C120.0712 (19)0.0475 (14)0.0393 (14)0.0113 (13)0.0021 (13)0.0026 (11)
C130.134 (3)0.0571 (18)0.0507 (17)0.0308 (19)0.0162 (18)0.0066 (14)
Geometric parameters (Å, º) top
Ni1—O11.840 (2)C5—C61.362 (3)
Ni1—N11.850 (2)C6—H60.9300
Ni1—N21.967 (2)C7—H70.9300
Ni1—N31.894 (2)C8—C91.506 (3)
Cl1—C31.736 (3)C8—H8A0.9700
Cl2—C51.745 (3)C8—H8B0.9700
O1—C21.307 (3)C9—H9A0.9700
N1—C71.284 (3)C9—H9B0.9700
N1—C81.467 (3)C10—C111.503 (4)
N2—C91.491 (3)C10—H10A0.9700
N2—C101.495 (3)C10—H10B0.9700
N2—C121.504 (3)C11—H11A0.9600
N3—N41.187 (3)C11—H11B0.9600
N4—N51.143 (3)C11—H11C0.9600
C1—C61.399 (3)C12—C131.515 (3)
C1—C21.410 (3)C12—H12A0.9700
C1—C71.439 (3)C12—H12B0.9700
C2—C31.418 (3)C13—H13A0.9600
C3—C41.367 (3)C13—H13B0.9600
C4—C51.382 (4)C13—H13C0.9600
C4—H40.9300
O1—Ni1—N193.87 (7)C1—C7—H7117.9
O1—Ni1—N2178.84 (7)N1—C8—C9105.95 (17)
O1—Ni1—N389.33 (8)N1—C8—H8A110.5
N1—Ni1—N286.83 (8)C9—C8—H8A110.5
N1—Ni1—N3176.76 (8)N1—C8—H8B110.5
N2—Ni1—N389.97 (9)C9—C8—H8B110.5
C2—O1—Ni1125.79 (14)H8A—C8—H8B108.7
C7—N1—C8118.86 (19)N2—C9—C8109.38 (18)
C7—N1—Ni1127.00 (15)N2—C9—H9A109.8
C8—N1—Ni1114.04 (14)C8—C9—H9A109.8
C9—N2—C10109.62 (18)N2—C9—H9B109.8
C9—N2—C12110.57 (18)C8—C9—H9B109.8
C10—N2—C12110.29 (18)H9A—C9—H9B108.2
C9—N2—Ni1107.33 (12)N2—C10—C11113.47 (19)
C10—N2—Ni1113.92 (14)N2—C10—H10A108.9
C12—N2—Ni1104.99 (14)C11—C10—H10A108.9
N4—N3—Ni1123.34 (18)N2—C10—H10B108.9
N5—N4—N3175.7 (3)C11—C10—H10B108.9
C6—C1—C2121.2 (2)H10A—C10—H10B107.7
C6—C1—C7118.3 (2)C10—C11—H11A109.5
C2—C1—C7120.6 (2)C10—C11—H11B109.5
O1—C2—C1124.84 (19)H11A—C11—H11B109.5
O1—C2—C3119.5 (2)C10—C11—H11C109.5
C1—C2—C3115.7 (2)H11A—C11—H11C109.5
C4—C3—C2122.9 (2)H11B—C11—H11C109.5
C4—C3—Cl1119.59 (19)N2—C12—C13116.3 (2)
C2—C3—Cl1117.47 (19)N2—C12—H12A108.2
C3—C4—C5119.0 (2)C13—C12—H12A108.2
C3—C4—H4120.5N2—C12—H12B108.2
C5—C4—H4120.5C13—C12—H12B108.2
C6—C5—C4121.2 (2)H12A—C12—H12B107.4
C6—C5—Cl2119.3 (2)C12—C13—H13A109.5
C4—C5—Cl2119.51 (19)C12—C13—H13B109.5
C5—C6—C1119.9 (2)H13A—C13—H13B109.5
C5—C6—H6120.0C12—C13—H13C109.5
C1—C6—H6120.0H13A—C13—H13C109.5
N1—C7—C1124.2 (2)H13B—C13—H13C109.5
N1—C7—H7117.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···N30.972.562.915 (2)102
C12—H12B···N30.972.593.125 (2)115
C13—H13A···N5i0.972.663.576 (4)159
Symmetry code: (i) x, y+1, z.
 

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