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In the title compound, [Ni(C15H12BrClN2O2)(C6H15N)], the NiII atom exists in square-planar geometry, coordinated by a mol­ecule of triethyl­amine through the N atom and by a tridentate Schiff base ligand via N and O atoms. No significant intermolecular interactions are found in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023554/cv6372sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023554/cv6372Isup2.hkl
Contains datablock I

CCDC reference: 252951

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.029
  • wR factor = 0.083
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O2 .. 5.07 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 O2 -NI1 -O1 -C1 -42.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 O1 -NI1 -O2 -C9 35.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 9 N3 -NI1 -N1 -C7 167.40 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 12 N3 -NI1 -N1 -N2 -12.10 1.40 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17 N1 -NI1 -N3 -C16 -104.50 1.30 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 20 N1 -NI1 -N3 -C18 139.10 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 23 N1 -NI1 -N3 -C20 16.50 1.40 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 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 1 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 8 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON ( Spek, 2003).

(5-Bromo-2-oxidoacetophenone 4-chlorobenzoylhydrazido)(triethylamine)nickel(II) top
Crystal data top
[Ni(C15H12BrClN2O2)(C6H15N)]Z = 2
Mr = 525.51F(000) = 536
Triclinic, P1Dx = 1.591 Mg m3
a = 9.846 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.410 (2) ÅCell parameters from 927 reflections
c = 12.253 (3) Åθ = 1.7–26.5°
α = 79.99 (4)°µ = 2.85 mm1
β = 85.74 (4)°T = 273 K
γ = 62.49 (3)°Block, dark red
V = 1097.0 (4) Å30.50 × 0.37 × 0.36 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4503 independent reflections
Radiation source: fine-focus sealed tube3916 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 83.66 pixels mm-1θmax = 26.5°, θmin = 1.7°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1213
Tmin = 0.277, Tmax = 0.359l = 1515
11547 measured reflections
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0473P)2 + 0.286P]
where P = (Fo2 + 2Fc2)/3
4503 reflections(Δ/σ)max < 0.001
266 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.37 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.22158 (3)0.73358 (3)0.22156 (2)0.03928 (9)
Br10.38895 (3)0.91565 (3)0.17136 (2)0.06293 (10)
Cl10.23181 (11)1.25434 (11)0.67585 (7)0.0888 (3)
O10.17696 (17)0.66658 (17)0.10907 (13)0.0533 (4)
O20.26526 (16)0.80498 (16)0.33432 (12)0.0470 (3)
N10.04107 (18)0.90625 (18)0.20972 (14)0.0384 (3)
N20.03264 (19)0.99922 (19)0.28244 (14)0.0424 (4)
N30.42293 (19)0.55063 (18)0.23972 (14)0.0419 (4)
C10.0496 (2)0.7283 (2)0.05115 (18)0.0445 (5)
C20.0397 (3)0.6534 (3)0.0306 (2)0.0566 (6)
H20.12250.56430.04030.068*
C30.0872 (3)0.7065 (3)0.0963 (2)0.0556 (6)
H30.09020.65480.15000.067*
C40.2105 (3)0.8383 (3)0.08150 (18)0.0470 (5)
C50.2065 (2)0.9154 (2)0.00327 (18)0.0448 (5)
H50.29141.00360.00540.054*
C60.0768 (2)0.8644 (2)0.06441 (17)0.0399 (4)
C70.0764 (2)0.9527 (2)0.14393 (17)0.0391 (4)
C80.2113 (3)1.0984 (2)0.1509 (2)0.0533 (5)
H8A0.29901.08440.17570.080*
H8B0.23221.15810.07910.080*
H8C0.18911.14620.20240.080*
C90.1565 (2)0.9349 (2)0.34314 (17)0.0405 (4)
C100.1746 (2)1.0134 (2)0.42568 (17)0.0423 (4)
C110.0598 (3)1.1495 (3)0.4420 (2)0.0556 (6)
H110.03031.19180.40070.067*
C120.0772 (3)1.2234 (3)0.5186 (2)0.0631 (7)
H120.00061.31500.52900.076*
C130.2092 (3)1.1613 (3)0.5793 (2)0.0561 (6)
C140.3257 (3)1.0265 (3)0.5651 (2)0.0609 (6)
H140.41540.98520.60680.073*
C150.3077 (3)0.9531 (3)0.4878 (2)0.0540 (5)
H150.38630.86190.47750.065*
C160.5070 (3)0.5480 (3)0.1335 (2)0.0547 (6)
H16A0.44420.55190.07450.066*
H16B0.59990.45560.13820.066*
C170.5494 (3)0.6710 (3)0.1033 (3)0.0700 (7)
H17A0.46180.76230.11180.105*
H17B0.58280.67440.02770.105*
H17C0.63060.65500.15100.105*
C180.3938 (3)0.4202 (3)0.2586 (2)0.0595 (6)
H18A0.49150.33240.26720.071*
H18B0.34390.42020.19320.071*
C190.2973 (4)0.4127 (4)0.3574 (3)0.0897 (10)
H19A0.34650.41050.42300.135*
H19B0.28480.32550.36400.135*
H19C0.19880.49730.34860.135*
C200.5172 (3)0.5454 (3)0.3331 (2)0.0574 (6)
H20A0.46100.54490.40150.069*
H20B0.52830.63470.32080.069*
C210.6765 (3)0.4149 (3)0.3487 (2)0.0723 (8)
H21A0.66760.32540.36200.109*
H21B0.72630.42050.41090.109*
H21C0.73570.41660.28320.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03458 (14)0.03792 (15)0.04102 (15)0.01069 (11)0.00421 (10)0.01098 (10)
Br10.05863 (16)0.07552 (19)0.05926 (17)0.03263 (14)0.02033 (12)0.00754 (12)
Cl10.1212 (7)0.1191 (7)0.0712 (5)0.0839 (6)0.0074 (4)0.0441 (4)
O10.0434 (8)0.0508 (9)0.0578 (9)0.0085 (7)0.0117 (7)0.0221 (7)
O20.0401 (8)0.0431 (8)0.0501 (8)0.0086 (6)0.0078 (6)0.0152 (6)
N10.0365 (8)0.0384 (8)0.0400 (8)0.0153 (7)0.0024 (7)0.0096 (7)
N20.0400 (9)0.0417 (9)0.0453 (9)0.0155 (7)0.0022 (7)0.0146 (7)
N30.0383 (9)0.0400 (9)0.0424 (9)0.0118 (7)0.0032 (7)0.0107 (7)
C10.0421 (11)0.0464 (11)0.0458 (11)0.0193 (9)0.0028 (9)0.0105 (9)
C20.0512 (13)0.0556 (13)0.0615 (14)0.0174 (11)0.0068 (11)0.0234 (11)
C30.0565 (14)0.0629 (14)0.0555 (13)0.0292 (12)0.0062 (11)0.0209 (11)
C40.0462 (11)0.0551 (12)0.0446 (11)0.0277 (10)0.0090 (9)0.0030 (9)
C50.0415 (11)0.0461 (11)0.0450 (11)0.0185 (9)0.0058 (9)0.0047 (9)
C60.0374 (10)0.0440 (10)0.0400 (10)0.0201 (8)0.0009 (8)0.0057 (8)
C70.0350 (9)0.0392 (10)0.0418 (10)0.0158 (8)0.0017 (8)0.0055 (8)
C80.0413 (11)0.0455 (12)0.0642 (14)0.0086 (9)0.0107 (10)0.0152 (10)
C90.0366 (10)0.0429 (10)0.0411 (10)0.0159 (8)0.0001 (8)0.0107 (8)
C100.0388 (10)0.0481 (11)0.0432 (11)0.0211 (9)0.0010 (8)0.0119 (9)
C110.0435 (12)0.0546 (13)0.0667 (15)0.0151 (10)0.0061 (11)0.0235 (11)
C120.0621 (15)0.0629 (15)0.0721 (17)0.0282 (12)0.0056 (13)0.0334 (13)
C130.0718 (16)0.0760 (16)0.0451 (12)0.0520 (14)0.0073 (11)0.0201 (11)
C140.0604 (15)0.0811 (18)0.0501 (13)0.0382 (14)0.0107 (11)0.0106 (12)
C150.0473 (12)0.0586 (13)0.0518 (13)0.0183 (10)0.0081 (10)0.0117 (10)
C160.0469 (12)0.0564 (13)0.0504 (13)0.0126 (10)0.0002 (10)0.0155 (10)
C170.0663 (17)0.0664 (16)0.0711 (17)0.0287 (14)0.0087 (14)0.0043 (13)
C180.0567 (14)0.0442 (12)0.0721 (16)0.0173 (10)0.0013 (12)0.0118 (11)
C190.101 (3)0.075 (2)0.097 (2)0.0488 (19)0.028 (2)0.0082 (17)
C200.0503 (13)0.0548 (13)0.0538 (13)0.0089 (11)0.0125 (10)0.0149 (10)
C210.0577 (15)0.0640 (16)0.0720 (17)0.0032 (13)0.0206 (13)0.0165 (13)
Geometric parameters (Å, º) top
Ni1—O11.8128 (15)C10—C111.383 (3)
Ni1—O21.8402 (15)C10—C151.383 (3)
Ni1—N11.8460 (16)C11—C121.378 (4)
Ni1—N32.0095 (16)C11—H110.9300
Br1—C41.902 (2)C12—C131.364 (4)
Cl1—C131.739 (2)C12—H120.9300
O1—C11.311 (3)C13—C141.372 (4)
O2—C91.297 (2)C14—C151.384 (3)
N1—C71.307 (3)C14—H140.9300
N1—N21.397 (2)C15—H150.9300
N2—C91.303 (3)C16—C171.502 (4)
N3—C161.487 (3)C16—H16A0.9700
N3—C181.490 (3)C16—H16B0.9700
N3—C201.505 (3)C17—H17A0.9600
C1—C21.406 (3)C17—H17B0.9600
C1—C61.415 (3)C17—H17C0.9600
C2—C31.368 (3)C18—C191.496 (4)
C2—H20.9300C18—H18A0.9700
C3—C41.380 (3)C18—H18B0.9700
C3—H30.9300C19—H19A0.9600
C4—C51.367 (3)C19—H19B0.9600
C5—C61.407 (3)C19—H19C0.9600
C5—H50.9300C20—C211.526 (3)
C6—C71.452 (3)C20—H20A0.9700
C7—C81.496 (3)C20—H20B0.9700
C8—H8A0.9600C21—H21A0.9600
C8—H8B0.9600C21—H21B0.9600
C8—H8C0.9600C21—H21C0.9600
C9—C101.473 (3)
O1—Ni1—O2178.96 (7)C12—C11—C10120.8 (2)
O1—Ni1—N194.99 (7)C12—C11—H11119.6
O2—Ni1—N184.19 (7)C10—C11—H11119.6
O1—Ni1—N388.15 (7)C13—C12—C11119.6 (2)
O2—Ni1—N392.65 (7)C13—C12—H12120.2
N1—Ni1—N3176.74 (7)C11—C12—H12120.2
C1—O1—Ni1127.24 (14)C12—C13—C14121.2 (2)
C9—O2—Ni1110.27 (13)C12—C13—Cl1119.7 (2)
C7—N1—N2116.74 (16)C14—C13—Cl1119.1 (2)
C7—N1—Ni1129.68 (14)C13—C14—C15119.0 (2)
N2—N1—Ni1113.58 (12)C13—C14—H14120.5
C9—N2—N1108.63 (16)C15—C14—H14120.5
C16—N3—C18107.59 (18)C10—C15—C14121.0 (2)
C16—N3—C20109.96 (18)C10—C15—H15119.5
C18—N3—C20110.45 (19)C14—C15—H15119.5
C16—N3—Ni1107.57 (13)N3—C16—C17114.5 (2)
C18—N3—Ni1109.07 (14)N3—C16—H16A108.6
C20—N3—Ni1112.06 (13)C17—C16—H16A108.6
O1—C1—C2117.01 (19)N3—C16—H16B108.6
O1—C1—C6124.80 (19)C17—C16—H16B108.6
C2—C1—C6118.2 (2)H16A—C16—H16B107.6
C3—C2—C1122.5 (2)C16—C17—H17A109.5
C3—C2—H2118.8C16—C17—H17B109.5
C1—C2—H2118.8H17A—C17—H17B109.5
C2—C3—C4118.8 (2)C16—C17—H17C109.5
C2—C3—H3120.6H17A—C17—H17C109.5
C4—C3—H3120.6H17B—C17—H17C109.5
C5—C4—C3120.9 (2)N3—C18—C19114.7 (2)
C5—C4—Br1119.06 (17)N3—C18—H18A108.6
C3—C4—Br1120.02 (17)C19—C18—H18A108.6
C4—C5—C6121.5 (2)N3—C18—H18B108.6
C4—C5—H5119.3C19—C18—H18B108.6
C6—C5—H5119.3H18A—C18—H18B107.6
C5—C6—C1118.08 (19)C18—C19—H19A109.5
C5—C6—C7119.33 (18)C18—C19—H19B109.5
C1—C6—C7122.58 (18)H19A—C19—H19B109.5
N1—C7—C6120.57 (18)C18—C19—H19C109.5
N1—C7—C8119.45 (18)H19A—C19—H19C109.5
C6—C7—C8119.99 (18)H19B—C19—H19C109.5
C7—C8—H8A109.5N3—C20—C21115.9 (2)
C7—C8—H8B109.5N3—C20—H20A108.3
H8A—C8—H8B109.5C21—C20—H20A108.3
C7—C8—H8C109.5N3—C20—H20B108.3
H8A—C8—H8C109.5C21—C20—H20B108.3
H8B—C8—H8C109.5H20A—C20—H20B107.4
O2—C9—N2123.22 (18)C20—C21—H21A109.5
O2—C9—C10118.24 (18)C20—C21—H21B109.5
N2—C9—C10118.54 (17)H21A—C21—H21B109.5
C11—C10—C15118.5 (2)C20—C21—H21C109.5
C11—C10—C9120.80 (19)H21A—C21—H21C109.5
C15—C10—C9120.69 (19)H21B—C21—H21C109.5
O2—Ni1—O1—C142 (4)C2—C1—C6—C7178.0 (2)
N1—Ni1—O1—C13.8 (2)N2—N1—C7—C6179.05 (17)
N3—Ni1—O1—C1177.1 (2)Ni1—N1—C7—C60.4 (3)
O1—Ni1—O2—C935 (4)N2—N1—C7—C80.8 (3)
N1—Ni1—O2—C92.87 (14)Ni1—N1—C7—C8179.65 (16)
N3—Ni1—O2—C9176.29 (14)C5—C6—C7—N1178.29 (19)
O1—Ni1—N1—C72.88 (19)C1—C6—C7—N12.3 (3)
O2—Ni1—N1—C7177.76 (19)C5—C6—C7—C81.8 (3)
N3—Ni1—N1—C7167.4 (12)C1—C6—C7—C8177.6 (2)
O1—Ni1—N1—N2176.63 (13)Ni1—O2—C9—N22.8 (3)
O2—Ni1—N1—N22.72 (13)Ni1—O2—C9—C10177.02 (15)
N3—Ni1—N1—N212.1 (14)N1—N2—C9—O20.6 (3)
C7—N1—N2—C9178.49 (18)N1—N2—C9—C10179.20 (17)
Ni1—N1—N2—C91.9 (2)O2—C9—C10—C11177.3 (2)
O1—Ni1—N3—C1660.04 (15)N2—C9—C10—C112.9 (3)
O2—Ni1—N3—C16119.31 (15)O2—C9—C10—C153.4 (3)
N1—Ni1—N3—C16104.5 (13)N2—C9—C10—C15176.4 (2)
O1—Ni1—N3—C1856.38 (15)C15—C10—C11—C120.3 (4)
O2—Ni1—N3—C18124.27 (15)C9—C10—C11—C12179.6 (2)
N1—Ni1—N3—C18139.1 (12)C10—C11—C12—C130.1 (4)
O1—Ni1—N3—C20178.99 (16)C11—C12—C13—C140.2 (4)
O2—Ni1—N3—C201.66 (16)C11—C12—C13—Cl1179.9 (2)
N1—Ni1—N3—C2016.5 (14)C12—C13—C14—C150.1 (4)
Ni1—O1—C1—C2178.29 (17)Cl1—C13—C14—C15179.70 (19)
Ni1—O1—C1—C62.3 (3)C11—C10—C15—C140.4 (4)
O1—C1—C2—C3180.0 (2)C9—C10—C15—C14179.7 (2)
C6—C1—C2—C30.6 (4)C13—C14—C15—C100.3 (4)
C1—C2—C3—C40.4 (4)C18—N3—C16—C17178.5 (2)
C2—C3—C4—C50.5 (4)C20—N3—C16—C1758.2 (3)
C2—C3—C4—Br1180.0 (2)Ni1—N3—C16—C1764.1 (2)
C3—C4—C5—C60.4 (3)C16—N3—C18—C19174.8 (2)
Br1—C4—C5—C6179.11 (16)C20—N3—C18—C1965.2 (3)
C4—C5—C6—C11.4 (3)Ni1—N3—C18—C1958.4 (3)
C4—C5—C6—C7178.10 (19)C16—N3—C20—C2156.8 (3)
O1—C1—C6—C5179.2 (2)C18—N3—C20—C2161.8 (3)
C2—C1—C6—C51.4 (3)Ni1—N3—C20—C21176.4 (2)
O1—C1—C6—C71.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8C···N20.962.192.672 (3)110
C16—H16A···O10.972.372.913 (4)114
C18—H18B···O10.972.402.896 (3)111
 

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