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In the title complex, [Ni(C28H20Cl2N2O2)], the NiII atom exists in a square-planar environment, coordinated by four atoms from the tetradentate ligand. Molecules are held together by intermolecular C—H...O hydrogen bonds, which link the mol­ecules in a chain along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009663/ng6023sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009663/ng6023Isup2.hkl
Contains datablock I

CCDC reference: 239112

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.058
  • wR factor = 0.148
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.620 0.898 Tmin' and Tmax expected: 0.821 0.898 RR' = 0.755 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.75 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 5 N1 -NI1 -O2 -C14 99.90 1.50 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

{N,N'-Bis[(5-chloro-2-hydroxyphenyl)phenylmethylene]ethylendiaminato}nickel(II) top
Crystal data top
[Ni(C28H20Cl2N2O2)]Z = 2
Mr = 546.07F(000) = 560
Triclinic, P1Dx = 1.532 Mg m3
a = 10.168 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.945 (5) ÅCell parameters from 840 reflections
c = 11.492 (6) Åθ = 3.3–25.1°
α = 68.232 (7)°µ = 1.08 mm1
β = 89.066 (8)°T = 293 K
γ = 85.532 (8)°Prism, red
V = 1184.0 (10) Å30.18 × 0.12 × 0.10 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
4133 independent reflections
Radiation source: fine-focus sealed tube2641 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 126
Tmin = 0.620, Tmax = 0.898k = 1313
6084 measured reflectionsl = 1312
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.074P)2]
where P = (Fo2 + 2Fc2)/3
4133 reflections(Δ/σ)max = 0.002
316 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.46 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.25830 (6)0.54090 (6)0.00439 (7)0.0299 (2)
Cl10.23268 (14)0.24641 (16)0.44933 (15)0.0545 (4)
Cl20.74402 (16)0.61205 (17)0.48104 (16)0.0614 (5)
O10.1787 (3)0.3874 (3)0.0737 (3)0.0385 (9)
O20.3469 (3)0.4513 (3)0.0918 (3)0.0358 (9)
N10.1529 (4)0.6340 (4)0.0733 (4)0.0313 (10)
N20.3520 (4)0.6892 (4)0.0739 (4)0.0292 (10)
C10.1369 (5)0.7493 (5)0.1420 (6)0.0400 (14)
H10.17190.72610.07950.048*
C20.2046 (5)0.8426 (5)0.1782 (6)0.0435 (15)
H20.28550.88150.14060.052*
C30.1543 (5)0.8785 (6)0.2685 (6)0.0469 (15)
H30.19910.94420.29020.056*
C40.0364 (6)0.8177 (6)0.3281 (6)0.0508 (16)
H40.00280.84050.39150.061*
C50.0309 (5)0.7229 (6)0.2928 (6)0.0462 (15)
H50.10950.68090.33350.055*
C60.0171 (5)0.6896 (5)0.1980 (5)0.0304 (12)
C70.0599 (5)0.5925 (5)0.1554 (5)0.0302 (12)
C80.0268 (5)0.4578 (5)0.2030 (5)0.0315 (12)
C90.0735 (5)0.4188 (5)0.2927 (5)0.0345 (13)
H90.11780.48110.31930.041*
C100.1060 (5)0.2928 (5)0.3404 (5)0.0371 (13)
C110.0381 (5)0.1961 (6)0.3072 (6)0.0444 (15)
H110.05790.10860.34430.053*
C120.0588 (6)0.2307 (5)0.2190 (6)0.0476 (16)
H120.10380.16590.19620.057*
C130.0914 (5)0.3619 (5)0.1624 (5)0.0337 (13)
C140.4318 (5)0.4961 (5)0.1819 (5)0.0320 (12)
C150.4691 (5)0.4159 (5)0.2514 (5)0.0380 (13)
H150.42960.33750.23480.046*
C160.5628 (5)0.4524 (5)0.3431 (5)0.0418 (14)
H160.58580.39940.38870.050*
C170.6223 (5)0.5681 (5)0.3668 (5)0.0376 (13)
C180.5870 (5)0.6507 (5)0.3061 (5)0.0363 (13)
H180.62790.72880.32500.044*
C190.4877 (5)0.6179 (5)0.2138 (5)0.0295 (12)
C200.4447 (5)0.7116 (5)0.1570 (5)0.0294 (12)
C210.5082 (5)0.8399 (4)0.1963 (5)0.0292 (12)
C220.4687 (5)0.9414 (5)0.3063 (6)0.0435 (14)
H220.40570.92900.35780.052*
C230.5227 (6)1.0616 (6)0.3400 (6)0.0530 (17)
H230.49581.13060.41380.064*
C240.6164 (6)1.0784 (6)0.2636 (7)0.0536 (18)
H240.65281.15920.28600.064*
C250.6565 (6)0.9780 (6)0.1555 (6)0.0504 (16)
H250.72010.99030.10450.060*
C260.6029 (5)0.8582 (5)0.1217 (6)0.0404 (14)
H260.63090.78950.04810.049*
C270.3150 (5)0.7860 (5)0.0155 (5)0.0396 (14)
H27A0.32750.87440.07430.048*
H27B0.37040.76850.05770.048*
C280.1744 (5)0.7756 (5)0.0216 (6)0.0436 (15)
H28A0.15570.81430.08410.052*
H28B0.11700.82140.05060.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0344 (4)0.0246 (4)0.0308 (4)0.0052 (3)0.0042 (3)0.0099 (3)
Cl10.0461 (9)0.0663 (10)0.0476 (10)0.0211 (7)0.0145 (7)0.0143 (8)
Cl20.0655 (10)0.0655 (11)0.0558 (12)0.0131 (8)0.0291 (9)0.0250 (9)
O10.047 (2)0.030 (2)0.042 (3)0.0129 (16)0.0160 (18)0.0161 (18)
O20.043 (2)0.0257 (19)0.043 (3)0.0096 (16)0.0139 (18)0.0164 (18)
N10.031 (2)0.025 (2)0.037 (3)0.0020 (18)0.006 (2)0.010 (2)
N20.034 (2)0.024 (2)0.032 (3)0.0014 (18)0.0042 (19)0.012 (2)
C10.042 (3)0.035 (3)0.044 (4)0.004 (2)0.002 (3)0.015 (3)
C20.035 (3)0.034 (3)0.060 (4)0.002 (2)0.000 (3)0.017 (3)
C30.049 (4)0.042 (4)0.057 (4)0.002 (3)0.010 (3)0.028 (3)
C40.057 (4)0.055 (4)0.053 (4)0.005 (3)0.004 (3)0.037 (4)
C50.049 (3)0.043 (4)0.050 (4)0.007 (3)0.010 (3)0.021 (3)
C60.034 (3)0.030 (3)0.028 (3)0.008 (2)0.004 (2)0.011 (2)
C70.029 (3)0.030 (3)0.033 (3)0.000 (2)0.001 (2)0.013 (2)
C80.035 (3)0.026 (3)0.028 (3)0.004 (2)0.000 (2)0.004 (2)
C90.036 (3)0.035 (3)0.034 (3)0.006 (2)0.002 (2)0.013 (3)
C100.034 (3)0.043 (3)0.031 (3)0.010 (2)0.002 (2)0.008 (3)
C110.050 (3)0.034 (3)0.047 (4)0.019 (3)0.014 (3)0.009 (3)
C120.057 (4)0.032 (3)0.061 (5)0.014 (3)0.015 (3)0.023 (3)
C130.034 (3)0.035 (3)0.035 (4)0.010 (2)0.003 (2)0.016 (3)
C140.033 (3)0.030 (3)0.032 (3)0.000 (2)0.007 (2)0.010 (3)
C150.049 (3)0.026 (3)0.041 (4)0.005 (2)0.009 (3)0.014 (3)
C160.057 (4)0.032 (3)0.037 (4)0.002 (3)0.004 (3)0.014 (3)
C170.041 (3)0.037 (3)0.031 (3)0.001 (2)0.008 (2)0.009 (3)
C180.036 (3)0.032 (3)0.039 (4)0.000 (2)0.004 (2)0.011 (3)
C190.030 (3)0.026 (3)0.033 (3)0.005 (2)0.001 (2)0.011 (2)
C200.029 (3)0.025 (3)0.033 (3)0.002 (2)0.006 (2)0.009 (2)
C210.034 (3)0.019 (3)0.032 (3)0.006 (2)0.008 (2)0.005 (2)
C220.044 (3)0.038 (3)0.046 (4)0.007 (3)0.004 (3)0.013 (3)
C230.069 (4)0.035 (3)0.042 (4)0.006 (3)0.013 (3)0.002 (3)
C240.061 (4)0.034 (4)0.071 (5)0.021 (3)0.023 (4)0.023 (4)
C250.055 (4)0.042 (4)0.058 (5)0.015 (3)0.004 (3)0.021 (3)
C260.045 (3)0.029 (3)0.047 (4)0.007 (2)0.001 (3)0.013 (3)
C270.055 (3)0.025 (3)0.041 (4)0.004 (2)0.009 (3)0.014 (3)
C280.050 (3)0.024 (3)0.055 (4)0.006 (2)0.011 (3)0.013 (3)
Geometric parameters (Å, º) top
Ni1—O11.831 (3)C11—H110.9300
Ni1—O21.830 (3)C12—C131.403 (7)
Ni1—N11.859 (4)C12—H120.9300
Ni1—N21.854 (4)C14—C191.409 (6)
Cl1—C101.749 (5)C14—C151.418 (7)
Cl2—C171.749 (5)C15—C161.375 (7)
O1—C131.304 (6)C15—H150.9300
O2—C141.310 (6)C16—C171.380 (7)
N1—C71.308 (6)C16—H160.9300
N1—C281.473 (6)C17—C181.357 (7)
N2—C201.301 (6)C18—C191.419 (7)
N2—C271.473 (6)C18—H180.9300
C1—C21.373 (7)C19—C201.444 (7)
C1—C61.384 (7)C20—C211.501 (6)
C1—H10.9300C21—C261.374 (7)
C2—C31.357 (8)C21—C221.378 (7)
C2—H20.9300C22—C231.383 (7)
C3—C41.384 (8)C22—H220.9300
C3—H30.9300C23—C241.373 (9)
C4—C51.379 (7)C23—H230.9300
C4—H40.9300C24—C251.361 (9)
C5—C61.377 (7)C24—H240.9300
C5—H50.9300C25—C261.376 (7)
C6—C71.492 (7)C25—H250.9300
C7—C81.435 (7)C26—H260.9300
C8—C91.411 (7)C27—C281.486 (7)
C8—C131.414 (7)C27—H27A0.9700
C9—C101.348 (7)C27—H27B0.9700
C9—H90.9300C28—H28A0.9700
C10—C111.385 (7)C28—H28B0.9700
C11—C121.372 (7)
O1—Ni1—O285.11 (15)C12—C13—C8118.4 (5)
O1—Ni1—N193.53 (16)O2—C14—C19124.4 (5)
O1—Ni1—N2174.79 (18)O2—C14—C15117.3 (4)
O2—Ni1—N1173.87 (18)C19—C14—C15118.3 (5)
O2—Ni1—N293.92 (16)C16—C15—C14121.0 (5)
N1—Ni1—N287.96 (17)C16—C15—H15119.5
C13—O1—Ni1128.4 (3)C14—C15—H15119.5
C14—O2—Ni1127.8 (3)C15—C16—C17119.4 (5)
C7—N1—C28119.1 (4)C15—C16—H16120.3
C7—N1—Ni1129.1 (3)C17—C16—H16120.3
C28—N1—Ni1111.5 (3)C18—C17—C16121.9 (5)
C20—N2—C27120.2 (4)C18—C17—Cl2118.9 (4)
C20—N2—Ni1129.1 (3)C16—C17—Cl2119.2 (4)
C27—N2—Ni1110.6 (3)C17—C18—C19120.0 (5)
C2—C1—C6120.4 (5)C17—C18—H18120.0
C2—C1—H1119.8C19—C18—H18120.0
C6—C1—H1119.8C14—C19—C18119.1 (5)
C3—C2—C1120.5 (5)C14—C19—C20121.8 (4)
C3—C2—H2119.8C18—C19—C20119.1 (4)
C1—C2—H2119.8N2—C20—C19122.3 (4)
C2—C3—C4120.1 (5)N2—C20—C21118.9 (4)
C2—C3—H3119.9C19—C20—C21118.8 (4)
C4—C3—H3119.9C26—C21—C22119.7 (5)
C5—C4—C3119.4 (6)C26—C21—C20120.5 (5)
C5—C4—H4120.3C22—C21—C20119.9 (5)
C3—C4—H4120.3C21—C22—C23120.0 (6)
C6—C5—C4120.8 (5)C21—C22—H22120.0
C6—C5—H5119.6C23—C22—H22120.0
C4—C5—H5119.6C24—C23—C22119.5 (6)
C5—C6—C1118.7 (5)C24—C23—H23120.3
C5—C6—C7120.5 (5)C22—C23—H23120.3
C1—C6—C7120.8 (5)C25—C24—C23120.7 (5)
N1—C7—C8122.3 (4)C25—C24—H24119.7
N1—C7—C6118.7 (4)C23—C24—H24119.7
C8—C7—C6118.9 (4)C24—C25—C26120.0 (6)
C9—C8—C13118.4 (4)C24—C25—H25120.0
C9—C8—C7119.6 (5)C26—C25—H25120.0
C13—C8—C7121.9 (4)C21—C26—C25120.2 (6)
C10—C9—C8121.1 (5)C21—C26—H26119.9
C10—C9—H9119.4C25—C26—H26119.9
C8—C9—H9119.4N2—C27—C28108.9 (4)
C9—C10—C11121.0 (5)N2—C27—H27A109.9
C9—C10—Cl1120.7 (4)C28—C27—H27A109.9
C11—C10—Cl1118.3 (4)N2—C27—H27B109.9
C12—C11—C10119.4 (5)C28—C27—H27B109.9
C12—C11—H11120.3H27A—C27—H27B108.3
C10—C11—H11120.3N1—C28—C27106.7 (4)
C11—C12—C13121.4 (5)N1—C28—H28A110.4
C11—C12—H12119.3C27—C28—H28A110.4
C13—C12—H12119.3N1—C28—H28B110.4
O1—C13—C12117.3 (5)C27—C28—H28B110.4
O1—C13—C8124.2 (4)H28A—C28—H28B108.6
O2—Ni1—O1—C13178.9 (5)C9—C8—C13—O1174.9 (5)
N1—Ni1—O1—C137.1 (5)C7—C8—C13—O14.9 (8)
O1—Ni1—O2—C14177.4 (4)C9—C8—C13—C124.0 (8)
N2—Ni1—O2—C147.8 (4)C7—C8—C13—C12176.2 (5)
N1—Ni1—O2—C1499.9 (15)Ni1—O2—C14—C1911.4 (7)
O1—Ni1—N1—C71.3 (5)Ni1—O2—C14—C15168.5 (4)
N2—Ni1—N1—C7173.7 (5)O2—C14—C15—C16176.6 (5)
O1—Ni1—N1—C28172.4 (4)C19—C14—C15—C163.5 (8)
N2—Ni1—N1—C2812.6 (4)C14—C15—C16—C170.6 (9)
O2—Ni1—N2—C201.1 (5)C15—C16—C17—C183.0 (9)
N1—Ni1—N2—C20173.1 (5)C15—C16—C17—Cl2178.6 (4)
O2—Ni1—N2—C27174.9 (3)C16—C17—C18—C191.1 (9)
N1—Ni1—N2—C2710.9 (4)Cl2—C17—C18—C19179.5 (4)
C6—C1—C2—C30.6 (8)O2—C14—C19—C18174.7 (5)
C1—C2—C3—C42.4 (9)C15—C14—C19—C185.4 (8)
C2—C3—C4—C51.6 (9)O2—C14—C19—C206.6 (8)
C3—C4—C5—C60.9 (9)C15—C14—C19—C20173.3 (5)
C4—C5—C6—C12.6 (8)C17—C18—C19—C143.2 (8)
C4—C5—C6—C7176.6 (5)C17—C18—C19—C20175.5 (5)
C2—C1—C6—C51.9 (8)C27—N2—C20—C19177.8 (5)
C2—C1—C6—C7177.3 (5)Ni1—N2—C20—C192.2 (7)
C28—N1—C7—C8175.3 (5)C27—N2—C20—C212.9 (7)
Ni1—N1—C7—C82.0 (8)Ni1—N2—C20—C21178.6 (4)
C28—N1—C7—C62.7 (7)C14—C19—C20—N20.3 (8)
Ni1—N1—C7—C6176.1 (4)C18—C19—C20—N2178.4 (5)
C5—C6—C7—N183.8 (7)C14—C19—C20—C21179.6 (5)
C1—C6—C7—N195.3 (6)C18—C19—C20—C210.9 (7)
C5—C6—C7—C898.0 (6)N2—C20—C21—C2678.8 (6)
C1—C6—C7—C882.8 (6)C19—C20—C21—C26101.9 (6)
N1—C7—C8—C9179.2 (5)N2—C20—C21—C2299.4 (6)
C6—C7—C8—C92.7 (7)C19—C20—C21—C2279.9 (6)
N1—C7—C8—C131.0 (8)C26—C21—C22—C231.1 (8)
C6—C7—C8—C13177.0 (5)C20—C21—C22—C23177.1 (5)
C13—C8—C9—C101.0 (8)C21—C22—C23—C240.5 (9)
C7—C8—C9—C10179.2 (5)C22—C23—C24—C250.1 (9)
C8—C9—C10—C112.9 (8)C23—C24—C25—C260.1 (9)
C8—C9—C10—Cl1178.8 (4)C22—C21—C26—C251.1 (8)
C9—C10—C11—C123.8 (9)C20—C21—C26—C25177.1 (5)
Cl1—C10—C11—C12177.9 (5)C24—C25—C26—C210.5 (9)
C10—C11—C12—C130.6 (9)C20—N2—C27—C28151.9 (5)
Ni1—O1—C13—C12171.4 (4)Ni1—N2—C27—C2831.7 (5)
Ni1—O1—C13—C89.7 (8)C7—N1—C28—C27153.2 (5)
C11—C12—C13—O1175.7 (6)Ni1—N1—C28—C2732.3 (5)
C11—C12—C13—C83.3 (9)N2—C27—C28—N140.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.932.513.385 (7)157
C26—H26···O2ii0.932.523.371 (7)152
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.
 

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