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In the title mononuclear compound, [Ni(C11H13BrClN2O)(NCS)], the NiII atom is four-coordinated in a square-planar geometry by one O and two N atoms of the Schiff base ligand, and by one N atom of the thio­cyanate anion. The mol­ecule possesses crystallographic mirror symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000451/ci2254sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000451/ci2254Isup2.hkl
Contains datablock I

CCDC reference: 636199

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in main residue
  • R factor = 0.043
  • wR factor = 0.109
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

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Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.95 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.16 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N3 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.12 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT412_ALERT_2_C Short Intra XH3 .. XHn H9B .. H10A .. 1.80 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: SHELXL97.

{2-Bromo-4-chloro-6-[2- (dimethylamino)ethyliminomethyl]phenolato)thiocyanatonickel(II) top
Crystal data top
[Ni(C11H13BrClN2O)(NCS)]F(000) = 840
Mr = 421.38Dx = 1.833 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 2673 reflections
a = 19.338 (1) Åθ = 2.5–24.3°
b = 6.994 (1) ŵ = 4.20 mm1
c = 11.288 (2) ÅT = 298 K
V = 1526.7 (4) Å3Block, red
Z = 40.17 × 0.15 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1717 independent reflections
Radiation source: fine-focus sealed tube1427 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2424
Tmin = 0.536, Tmax = 0.633k = 88
11929 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0414P)2 + 3.2149P]
where P = (Fo2 + 2Fc2)/3
1717 reflections(Δ/σ)max = 0.001
122 parametersΔρmax = 0.82 e Å3
9 restraintsΔρmin = 1.00 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)
Ni10.17445 (4)0.25000.35860 (7)0.0358 (3)
Br10.10816 (5)0.25000.77663 (7)0.0797 (4)
Cl10.16348 (9)0.25000.63950 (18)0.0648 (6)
S10.40632 (10)0.25000.4717 (2)0.0670 (6)
N10.0866 (3)0.25000.2767 (5)0.0422 (13)
N30.2652 (3)0.25000.4285 (6)0.0607 (18)
O10.1309 (2)0.25000.5110 (4)0.0453 (12)
C10.0650 (3)0.25000.5351 (5)0.0351 (14)
C20.0419 (3)0.25000.6544 (6)0.0408 (15)
C30.0263 (3)0.25000.6849 (6)0.0420 (16)
H30.03920.25000.76430.050*
C40.0759 (4)0.25000.5977 (6)0.0458 (17)
C50.0578 (3)0.25000.4809 (6)0.0454 (16)
H50.09190.25000.42300.054*
C60.0120 (3)0.25000.4478 (6)0.0375 (14)
C70.0267 (3)0.25000.3238 (6)0.0407 (15)
H70.01090.25000.27250.049*
C80.0928 (4)0.25000.1462 (6)0.064 (2)
H8A0.09160.37870.11680.076*0.50
H8B0.05500.18060.11200.076*0.50
C110.3239 (4)0.25000.4465 (6)0.0484 (17)
N20.2153 (3)0.25000.1893 (5)0.0553 (17)
C90.1567 (4)0.1701 (17)0.1131 (8)0.059 (3)0.50
H9A0.16640.19060.03070.071*0.50
H9B0.15440.03490.12720.071*0.50
C100.2622 (4)0.0841 (10)0.1712 (7)0.104 (3)
H10A0.23750.03240.18640.155*
H10B0.30070.09350.22460.155*
H10C0.27870.08390.09100.155*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0272 (4)0.0529 (5)0.0272 (4)0.0000.0019 (3)0.000
Br10.0565 (5)0.1473 (10)0.0353 (4)0.0000.0060 (4)0.000
Cl10.0343 (9)0.1079 (17)0.0522 (11)0.0000.0133 (8)0.000
S10.0368 (10)0.1004 (18)0.0637 (14)0.0000.0047 (9)0.000
N10.039 (3)0.060 (4)0.027 (3)0.0000.000 (2)0.000
N30.040 (3)0.103 (6)0.040 (3)0.0000.002 (3)0.000
O10.032 (2)0.074 (3)0.030 (2)0.0000.0007 (18)0.000
C10.034 (3)0.038 (3)0.034 (3)0.0000.001 (3)0.000
C20.042 (4)0.047 (4)0.033 (3)0.0000.002 (3)0.000
C30.045 (4)0.049 (4)0.032 (3)0.0000.009 (3)0.000
C40.037 (3)0.055 (4)0.046 (4)0.0000.013 (3)0.000
C50.033 (3)0.058 (4)0.045 (4)0.0000.001 (3)0.000
C60.033 (3)0.044 (4)0.035 (3)0.0000.004 (3)0.000
C70.032 (3)0.055 (4)0.035 (3)0.0000.003 (3)0.000
C80.047 (4)0.117 (7)0.027 (4)0.0000.000 (3)0.000
C110.041 (4)0.073 (5)0.032 (3)0.0000.002 (3)0.000
N20.036 (3)0.097 (5)0.033 (3)0.0000.005 (3)0.000
C90.047 (5)0.096 (9)0.034 (5)0.004 (5)0.001 (4)0.005 (5)
C100.154 (7)0.075 (5)0.082 (5)0.002 (5)0.067 (5)0.009 (4)
Geometric parameters (Å, º) top
Ni1—O11.915 (5)C5—C61.399 (9)
Ni1—N31.925 (6)C5—H50.93
Ni1—N11.934 (6)C6—C71.429 (9)
Ni1—N22.068 (6)C7—H70.93
Br1—C21.884 (7)C8—C9i1.406 (12)
Cl1—C41.758 (7)C8—C91.406 (12)
S1—C111.619 (7)C8—H8A0.96
N1—C71.274 (8)C8—H8B0.96
N1—C81.478 (9)N2—C10i1.487 (7)
N3—C111.152 (9)N2—C101.487 (7)
O1—C11.304 (8)N2—C91.528 (8)
C1—C21.419 (9)N2—C9i1.528 (8)
C1—C61.422 (9)C9—H9A0.96
C2—C31.362 (9)C9—H9B0.96
C3—C41.375 (10)C10—H10A0.96
C3—H30.93C10—H10B0.96
C4—C51.365 (10)C10—H10C0.96
O1—Ni1—N391.9 (2)C9i—C8—C946.8 (10)
O1—Ni1—N192.5 (2)C9i—C8—N1109.6 (6)
N3—Ni1—N1175.6 (2)C9—C8—N1109.6 (6)
O1—Ni1—N2176.4 (2)C9i—C8—H8A63.8
N3—Ni1—N291.7 (2)C9—C8—H8A107.7
N1—Ni1—N283.9 (2)N1—C8—H8A110.0
C7—N1—C8119.3 (6)C9i—C8—H8B139.9
C7—N1—Ni1126.8 (5)C9—C8—H8B111.2
C8—N1—Ni1113.9 (4)N1—C8—H8B109.8
C11—N3—Ni1166.0 (6)H8A—C8—H8B108.4
C1—O1—Ni1128.1 (4)N3—C11—S1179.9 (7)
O1—C1—C2120.4 (6)C10i—N2—C10102.6 (7)
O1—C1—C6124.1 (6)C10i—N2—C9131.3 (7)
C2—C1—C6115.5 (6)C10—N2—C995.2 (6)
C3—C2—C1123.0 (6)C10i—N2—C9i95.2 (6)
C3—C2—Br1118.3 (5)C10—N2—C9i131.3 (7)
C1—C2—Br1118.8 (5)C10i—N2—Ni1111.1 (4)
C2—C3—C4119.7 (6)C10—N2—Ni1111.1 (4)
C2—C3—H3120.2C9—N2—Ni1103.7 (5)
C4—C3—H3120.2C9i—N2—Ni1103.7 (5)
C5—C4—C3120.8 (6)C8—C9—N2110.9 (7)
C5—C4—Cl1120.5 (6)C8—C9—H9A111.7
C3—C4—Cl1118.7 (5)N2—C9—H9A110.2
C4—C5—C6120.4 (7)C8—C9—H9B107.8
C4—C5—H5119.8N2—C9—H9B107.5
C6—C5—H5119.8H9A—C9—H9B108.5
C5—C6—C1120.6 (6)N2—C10—H10A109.5
C5—C6—C7117.0 (6)N2—C10—H10B109.5
C1—C6—C7122.3 (6)H10A—C10—H10B109.5
N1—C7—C6126.2 (6)N2—C10—H10C109.5
N1—C7—H7116.9H10A—C10—H10C109.5
C6—C7—H7116.9H10B—C10—H10C109.5
Symmetry code: (i) x, y+1/2, z.
 

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