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The title compound, [Ni(C12H16BrN2O)2], crystallizes with two half-mol­ecules per asymmetric unit; each mononuclear mol­ecule is centrosymmetric. The NiII atom in each mol­ecule, lying on an inversion centre, is six-coordinated in a slightly distorted octa­hedral geometry by two phenolate O atoms, two imine N atoms and two amine N atoms from two Schiff base ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006575/ci2291sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006575/ci2291Isup2.hkl
Contains datablock I

CCDC reference: 640300

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.047
  • wR factor = 0.104
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.92
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.919 Tmax scaled 0.500 Tmin scaled 0.433
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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: SHELXTL.

Bis{4-bromo-2-[3-(dimethylamino)propyliminomethyl]phenolato}nickel(II) top
Crystal data top
[Ni(C12H16BrN2O)2]F(000) = 1272
Mr = 627.07Dx = 1.604 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3876 reflections
a = 10.111 (2) Åθ = 2.3–24.5°
b = 14.812 (2) ŵ = 3.85 mm1
c = 17.560 (3) ÅT = 298 K
β = 99.029 (2)°Block, green
V = 2597.3 (8) Å30.23 × 0.18 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
5926 independent reflections
Radiation source: fine-focus sealed tube3797 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.471, Tmax = 0.544k = 1919
21991 measured reflectionsl = 2222
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0396P)2 + 1.0211P]
where P = (Fo2 + 2Fc2)/3
5926 reflections(Δ/σ)max < 0.001
305 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.61 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
Ni11.00001.00000.00000.03328 (17)
Ni20.50000.50000.00000.03749 (18)
Br11.11954 (5)0.62826 (3)0.29256 (3)0.06612 (17)
Br20.91508 (5)0.25777 (4)0.32438 (3)0.07211 (18)
O11.1296 (2)0.95381 (17)0.08987 (14)0.0421 (6)
O20.6314 (3)0.52139 (16)0.09536 (14)0.0447 (7)
N10.8570 (3)0.9188 (2)0.03533 (17)0.0387 (7)
N20.9146 (3)1.1022 (2)0.07796 (18)0.0435 (8)
N30.4548 (3)0.3777 (2)0.04460 (17)0.0416 (8)
N40.3210 (3)0.5448 (2)0.06089 (18)0.0454 (8)
C11.0044 (4)0.8293 (3)0.1292 (2)0.0386 (9)
C21.1214 (4)0.8831 (2)0.1315 (2)0.0370 (9)
C31.2345 (4)0.8560 (3)0.1850 (2)0.0513 (11)
H31.31250.89020.18900.062*
C41.2329 (4)0.7817 (3)0.2306 (2)0.0534 (11)
H41.30900.76590.26500.064*
C51.1186 (4)0.7300 (3)0.2258 (2)0.0446 (10)
C61.0064 (4)0.7537 (3)0.1768 (2)0.0438 (10)
H60.92940.71890.17490.053*
C70.8782 (4)0.8555 (3)0.0853 (2)0.0404 (9)
H70.80360.82280.09420.048*
C80.7166 (4)0.9472 (3)0.0112 (2)0.0469 (10)
H8A0.65680.89770.01810.056*
H8B0.70250.96370.04290.056*
C90.6867 (4)1.0271 (3)0.0594 (3)0.0539 (11)
H9A0.59291.04250.04480.065*
H9B0.69931.00830.11290.065*
C100.7683 (4)1.1116 (3)0.0539 (3)0.0539 (11)
H10A0.75221.13250.00090.065*
H10B0.73601.15800.08530.065*
C110.9455 (4)1.0756 (3)0.1599 (2)0.0563 (12)
H11A1.04071.07670.17610.085*
H11B0.91241.01580.16620.085*
H11C0.90351.11710.19070.085*
C120.9751 (4)1.1917 (3)0.0708 (3)0.0563 (12)
H12A0.95511.21170.01820.084*
H12B1.07041.18770.08580.084*
H12C0.93921.23390.10360.084*
C130.6440 (4)0.3719 (3)0.1481 (2)0.0400 (9)
C140.6896 (4)0.4623 (3)0.1431 (2)0.0409 (9)
C150.8062 (4)0.4867 (3)0.1945 (2)0.0529 (11)
H150.83860.54530.19300.063*
C160.8728 (4)0.4269 (3)0.2464 (2)0.0562 (12)
H160.95000.44480.27890.067*
C170.8251 (4)0.3402 (3)0.2504 (2)0.0505 (11)
C180.7126 (4)0.3131 (3)0.2030 (2)0.0470 (10)
H180.68080.25460.20710.056*
C190.5231 (4)0.3388 (3)0.1026 (2)0.0451 (10)
H190.49160.28330.11690.054*
C200.3219 (4)0.3393 (3)0.0164 (2)0.0537 (12)
H20A0.32120.27570.02950.064*
H20B0.30250.34470.03930.064*
C210.2155 (5)0.3885 (3)0.0524 (3)0.0610 (13)
H21A0.12980.36000.03480.073*
H21B0.23510.38070.10790.073*
C220.2019 (4)0.4883 (3)0.0353 (3)0.0562 (11)
H22A0.17700.49570.02000.067*
H22B0.12850.51140.05920.067*
C230.3585 (4)0.5399 (3)0.1455 (2)0.0570 (12)
H23A0.28180.55350.16950.085*
H23B0.42830.58280.16210.085*
H23C0.38980.48020.16000.085*
C240.2842 (5)0.6393 (3)0.0420 (3)0.0581 (12)
H24A0.25550.64480.01260.087*
H24B0.36050.67740.05730.087*
H24C0.21280.65710.06880.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0305 (4)0.0341 (4)0.0338 (4)0.0029 (3)0.0006 (3)0.0020 (3)
Ni20.0491 (4)0.0285 (4)0.0320 (4)0.0053 (3)0.0026 (3)0.0020 (3)
Br10.0915 (4)0.0520 (3)0.0567 (3)0.0156 (3)0.0171 (3)0.0197 (2)
Br20.0705 (3)0.0926 (4)0.0536 (3)0.0422 (3)0.0109 (2)0.0229 (3)
O10.0354 (15)0.0487 (16)0.0388 (15)0.0047 (12)0.0047 (12)0.0066 (13)
O20.0569 (18)0.0349 (15)0.0375 (15)0.0057 (13)0.0071 (13)0.0046 (12)
N10.0334 (18)0.0406 (19)0.0405 (18)0.0046 (14)0.0012 (14)0.0033 (15)
N20.044 (2)0.045 (2)0.0406 (19)0.0012 (16)0.0040 (15)0.0060 (15)
N30.054 (2)0.0318 (17)0.0376 (18)0.0077 (15)0.0039 (16)0.0016 (14)
N40.049 (2)0.046 (2)0.0406 (19)0.0027 (16)0.0041 (16)0.0023 (16)
C10.038 (2)0.041 (2)0.036 (2)0.0007 (18)0.0033 (17)0.0036 (17)
C20.039 (2)0.037 (2)0.035 (2)0.0038 (17)0.0038 (17)0.0003 (17)
C30.042 (2)0.054 (3)0.054 (3)0.004 (2)0.005 (2)0.008 (2)
C40.054 (3)0.057 (3)0.047 (3)0.013 (2)0.002 (2)0.007 (2)
C50.060 (3)0.040 (2)0.037 (2)0.013 (2)0.017 (2)0.0049 (18)
C60.047 (2)0.044 (2)0.043 (2)0.0016 (19)0.0124 (19)0.0023 (19)
C70.035 (2)0.045 (2)0.042 (2)0.0101 (18)0.0081 (18)0.0020 (18)
C80.029 (2)0.054 (3)0.055 (3)0.0062 (19)0.0034 (19)0.004 (2)
C90.030 (2)0.072 (3)0.059 (3)0.009 (2)0.009 (2)0.003 (2)
C100.053 (3)0.054 (3)0.054 (3)0.011 (2)0.007 (2)0.009 (2)
C110.065 (3)0.064 (3)0.040 (2)0.002 (2)0.008 (2)0.013 (2)
C120.067 (3)0.045 (3)0.057 (3)0.003 (2)0.010 (2)0.014 (2)
C130.049 (2)0.040 (2)0.032 (2)0.0068 (19)0.0084 (18)0.0052 (17)
C140.050 (3)0.042 (2)0.030 (2)0.0003 (19)0.0063 (18)0.0005 (18)
C150.052 (3)0.051 (3)0.052 (3)0.008 (2)0.006 (2)0.002 (2)
C160.045 (3)0.075 (3)0.046 (3)0.007 (2)0.002 (2)0.003 (2)
C170.049 (3)0.062 (3)0.041 (2)0.021 (2)0.009 (2)0.013 (2)
C180.055 (3)0.044 (2)0.044 (2)0.008 (2)0.017 (2)0.0098 (19)
C190.061 (3)0.031 (2)0.044 (2)0.0053 (19)0.010 (2)0.0077 (18)
C200.068 (3)0.034 (2)0.054 (3)0.020 (2)0.005 (2)0.002 (2)
C210.057 (3)0.063 (3)0.063 (3)0.022 (2)0.008 (2)0.001 (2)
C220.047 (3)0.065 (3)0.057 (3)0.002 (2)0.010 (2)0.007 (2)
C230.066 (3)0.062 (3)0.044 (3)0.001 (2)0.011 (2)0.003 (2)
C240.073 (3)0.047 (3)0.056 (3)0.009 (2)0.014 (2)0.000 (2)
Geometric parameters (Å, º) top
Ni1—O1i2.007 (2)C8—H8A0.97
Ni1—O12.007 (2)C8—H8B0.97
Ni1—N1i2.050 (3)C9—C101.510 (6)
Ni1—N12.050 (3)C9—H9A0.97
Ni1—N22.298 (3)C9—H9B0.97
Ni1—N2i2.298 (3)C10—H10A0.97
Ni2—O2ii1.993 (2)C10—H10B0.97
Ni2—O21.993 (2)C11—H11A0.96
Ni2—N32.054 (3)C11—H11B0.96
Ni2—N3ii2.054 (3)C11—H11C0.96
Ni2—N42.338 (3)C12—H12A0.96
Ni2—N4ii2.338 (3)C12—H12B0.96
Br1—C51.908 (4)C12—H12C0.96
Br2—C171.907 (4)C13—C181.400 (5)
O1—C21.288 (4)C13—C141.424 (5)
O2—C141.289 (4)C13—C191.437 (5)
N1—C71.279 (4)C14—C151.414 (5)
N1—C81.477 (4)C15—C161.370 (5)
N2—C121.474 (5)C15—H150.93
N2—C111.477 (5)C16—C171.377 (6)
N2—C101.480 (5)C16—H160.93
N3—C191.275 (5)C17—C181.360 (6)
N3—C201.471 (5)C18—H180.93
N4—C241.472 (5)C19—H190.93
N4—C231.476 (5)C20—C211.517 (6)
N4—C221.478 (5)C20—H20A0.97
C1—C61.396 (5)C20—H20B0.97
C1—C21.421 (5)C21—C221.509 (6)
C1—C71.437 (5)C21—H21A0.97
C2—C31.419 (5)C21—H21B0.97
C3—C41.363 (5)C22—H22A0.97
C3—H30.93C22—H22B0.97
C4—C51.379 (6)C23—H23A0.96
C4—H40.93C23—H23B0.96
C5—C61.358 (5)C23—H23C0.96
C6—H60.93C24—H24A0.96
C7—H70.93C24—H24B0.96
C8—C91.512 (6)C24—H24C0.96
O1i—Ni1—O1180H8A—C8—H8B108.3
O1i—Ni1—N1i88.09 (11)C10—C9—C8117.0 (3)
O1—Ni1—N1i91.91 (11)C10—C9—H9A108.1
O1i—Ni1—N191.91 (11)C8—C9—H9A108.1
O1—Ni1—N188.09 (11)C10—C9—H9B108.1
N1i—Ni1—N1180C8—C9—H9B108.1
O1i—Ni1—N289.08 (11)H9A—C9—H9B107.3
O1—Ni1—N290.92 (11)N2—C10—C9115.8 (3)
N1i—Ni1—N298.23 (12)N2—C10—H10A108.3
N1—Ni1—N281.77 (12)C9—C10—H10A108.3
O1i—Ni1—N2i90.92 (11)N2—C10—H10B108.3
O1—Ni1—N2i89.08 (11)C9—C10—H10B108.3
N1i—Ni1—N2i81.77 (12)H10A—C10—H10B107.4
N1—Ni1—N2i98.23 (12)N2—C11—H11A109.5
N2—Ni1—N2i180N2—C11—H11B109.5
O2ii—Ni2—O2180H11A—C11—H11B109.5
O2ii—Ni2—N391.22 (11)N2—C11—H11C109.5
O2—Ni2—N388.78 (11)H11A—C11—H11C109.5
O2ii—Ni2—N3ii88.78 (11)H11B—C11—H11C109.5
O2—Ni2—N3ii91.22 (11)N2—C12—H12A109.5
N3—Ni2—N3ii180N2—C12—H12B109.5
O2ii—Ni2—N488.15 (11)H12A—C12—H12B109.5
O2—Ni2—N491.85 (11)N2—C12—H12C109.5
N3—Ni2—N480.88 (12)H12A—C12—H12C109.5
N3ii—Ni2—N499.12 (12)H12B—C12—H12C109.5
O2ii—Ni2—N4ii91.85 (11)C18—C13—C14119.9 (4)
O2—Ni2—N4ii88.15 (11)C18—C13—C19117.1 (4)
N3—Ni2—N4ii99.12 (12)C14—C13—C19122.8 (3)
N3ii—Ni2—N4ii80.88 (12)O2—C14—C15119.5 (4)
N4—Ni2—N4ii180.0O2—C14—C13124.0 (4)
C2—O1—Ni1129.2 (2)C15—C14—C13116.5 (4)
C14—O2—Ni2127.9 (2)C16—C15—C14122.2 (4)
C7—N1—C8117.1 (3)C16—C15—H15118.9
C7—N1—Ni1126.0 (3)C14—C15—H15118.9
C8—N1—Ni1116.0 (2)C15—C16—C17119.8 (4)
C12—N2—C11107.2 (3)C15—C16—H16120.1
C12—N2—C10107.5 (3)C17—C16—H16120.1
C11—N2—C10110.7 (3)C18—C17—C16120.7 (4)
C12—N2—Ni1110.0 (2)C18—C17—Br2119.4 (3)
C11—N2—Ni1111.3 (2)C16—C17—Br2119.8 (3)
C10—N2—Ni1110.1 (2)C17—C18—C13120.9 (4)
C19—N3—C20116.5 (3)C17—C18—H18119.6
C19—N3—Ni2125.3 (3)C13—C18—H18119.6
C20—N3—Ni2117.3 (2)N3—C19—C13126.6 (4)
C24—N4—C23106.8 (3)N3—C19—H19116.7
C24—N4—C22107.7 (3)C13—C19—H19116.7
C23—N4—C22110.3 (3)N3—C20—C21110.1 (3)
C24—N4—Ni2110.6 (2)N3—C20—H20A109.6
C23—N4—Ni2110.6 (2)C21—C20—H20A109.6
C22—N4—Ni2110.6 (2)N3—C20—H20B109.6
C6—C1—C2119.9 (4)C21—C20—H20B109.6
C6—C1—C7117.8 (3)H20A—C20—H20B108.1
C2—C1—C7121.9 (3)C22—C21—C20115.9 (4)
O1—C2—C3119.2 (3)C22—C21—H21A108.3
O1—C2—C1124.5 (3)C20—C21—H21A108.3
C3—C2—C1116.2 (3)C22—C21—H21B108.3
C4—C3—C2122.3 (4)C20—C21—H21B108.3
C4—C3—H3118.9H21A—C21—H21B107.4
C2—C3—H3118.9N4—C22—C21116.7 (4)
C3—C4—C5120.0 (4)N4—C22—H22A108.1
C3—C4—H4120.0C21—C22—H22A108.1
C5—C4—H4120.0N4—C22—H22B108.1
C6—C5—C4120.3 (4)C21—C22—H22B108.1
C6—C5—Br1121.1 (3)H22A—C22—H22B107.3
C4—C5—Br1118.6 (3)N4—C23—H23A109.5
C5—C6—C1121.3 (4)N4—C23—H23B109.5
C5—C6—H6119.4H23A—C23—H23B109.5
C1—C6—H6119.4N4—C23—H23C109.5
N1—C7—C1127.2 (3)H23A—C23—H23C109.5
N1—C7—H7116.4H23B—C23—H23C109.5
C1—C7—H7116.4N4—C24—H24A109.5
N1—C8—C9109.3 (3)N4—C24—H24B109.5
N1—C8—H8A109.8H24A—C24—H24B109.5
C9—C8—H8A109.8N4—C24—H24C109.5
N1—C8—H8B109.8H24A—C24—H24C109.5
C9—C8—H8B109.8H24B—C24—H24C109.5
Symmetry codes: (i) x+2, y+2, z; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O1i0.972.342.930 (3)118
C10—H10A···O1i0.972.493.032 (3)115
C20—H20B···O2ii0.972.362.937 (3)118
C22—H22A···O2ii0.972.523.056 (3)114
Symmetry codes: (i) x+2, y+2, z; (ii) x+1, y+1, z.
 

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