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The title compound, [Ni(C9H9Br2NO4S)(C8H8N2)(H2O)]·C2H5OH, was synthesized in a water–ethanol solution. In the structure, the Ni atom is six-coordinated by three ligands to form the neutral complex, in which the Ni atom has a distorted octahedral coordination geometry. Molecules form dimers through O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003119/lh6357sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003119/lh6357Isup2.hkl
Contains datablock I

CCDC reference: 269811

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.044
  • wR factor = 0.093
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT213_ALERT_2_C Atom C3 has ADP max/min Ratio ............. 3.40 prolat PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.75 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 5.18 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.27 su PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O3 .. 3.09 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Aqua{2-[(E)-(3,5-dibromo-2-oxidophenyl)methyleneamino]ethanesulfonato- κ3O,N,O'}(1,10-phenanthroline-κ2N,N')nickel(II) ethanol solvate top
Crystal data top
[Ni(C9H9Br2NO4S)(C8H8N2)(H2O)]·C2H6OF(000) = 2752
Mr = 688.03Dx = 1.738 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 33 reflections
a = 18.725 (4) Åθ = 2.8–14.1°
b = 19.623 (4) ŵ = 3.90 mm1
c = 15.647 (3) ÅT = 296 K
β = 113.82 (1)°Plate, blue
V = 5259.6 (19) Å30.54 × 0.38 × 0.36 mm
Z = 8
Data collection top
Siemens P4
diffractometer
2204 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 25.3°, θmin = 1.6°
ω scansh = 022
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 023
Tmin = 0.165, Tmax = 0.246l = 1817
5341 measured reflections3 standard reflections every 97 reflections
4776 independent reflections intensity decay: 1.1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0406P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.80(Δ/σ)max = 0.001
4776 reflectionsΔρmax = 0.49 e Å3
340 parametersΔρmin = 0.62 e Å3
3 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00032 (4)
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
Ni0.51779 (4)0.78170 (3)0.59556 (5)0.0298 (2)
Br10.27201 (4)0.71274 (4)0.61609 (5)0.0740 (3)
Br20.35565 (6)0.43891 (4)0.61097 (7)0.1218 (4)
S0.67045 (8)0.81258 (7)0.54816 (11)0.0363 (4)
O10.4361 (2)0.73777 (18)0.6297 (2)0.0411 (10)
O20.60327 (19)0.83451 (17)0.5676 (2)0.0378 (10)
O30.7432 (2)0.82907 (19)0.6256 (3)0.0518 (11)
O40.6652 (2)0.8363 (2)0.4589 (3)0.0545 (12)
O50.5732 (2)0.8187 (2)0.7304 (3)0.0365 (10)
N10.5807 (2)0.6924 (2)0.6227 (3)0.0350 (11)
N20.4596 (2)0.7638 (2)0.4508 (3)0.0342 (12)
N30.4549 (2)0.8732 (2)0.5517 (3)0.0338 (11)
C10.4212 (3)0.6728 (3)0.6256 (4)0.0421 (16)
C20.3495 (3)0.6478 (3)0.6217 (4)0.0490 (18)
C30.3316 (4)0.5805 (4)0.6183 (4)0.070 (2)
H30.28300.56730.61550.084*
C40.3844 (5)0.5314 (4)0.6188 (5)0.074 (2)
C50.4559 (4)0.5514 (3)0.6251 (4)0.0589 (19)
H50.49250.51870.62700.071*
C60.4753 (3)0.6209 (3)0.6288 (4)0.0418 (16)
C70.5525 (3)0.6356 (3)0.6328 (4)0.0400 (15)
H70.58590.59840.64430.048*
C80.6607 (3)0.6916 (3)0.6281 (4)0.0502 (17)
H8A0.67920.64490.63480.060*
H8B0.69430.71660.68320.060*
C90.6667 (3)0.7227 (3)0.5429 (4)0.0428 (15)
H9A0.62200.70870.48750.051*
H9B0.71340.70570.53740.051*
C100.4571 (3)0.7091 (3)0.4008 (4)0.0462 (16)
H100.47700.66850.43200.055*
C110.4262 (3)0.7091 (4)0.3040 (4)0.0583 (19)
H110.42600.66900.27230.070*
C120.3967 (4)0.7661 (4)0.2557 (5)0.060 (2)
H120.37660.76640.19080.072*
C130.3969 (3)0.8253 (3)0.3058 (4)0.0462 (17)
C140.3659 (4)0.8891 (4)0.2620 (5)0.067 (2)
H140.34610.89230.19720.080*
C150.3648 (4)0.9451 (4)0.3127 (5)0.068 (2)
H150.34570.98630.28280.081*
C160.3931 (3)0.9404 (3)0.4123 (4)0.0442 (16)
C170.3912 (3)0.9958 (3)0.4690 (5)0.058 (2)
H170.37091.03760.44220.070*
C180.4192 (3)0.9873 (3)0.5624 (5)0.0551 (18)
H180.41691.02320.59990.066*
C190.4513 (3)0.9257 (3)0.6032 (4)0.0488 (17)
H190.47080.92120.66780.059*
C200.4259 (3)0.8802 (3)0.4575 (4)0.0323 (14)
C210.4269 (3)0.8219 (3)0.4027 (4)0.0344 (14)
O60.7096 (3)0.8902 (3)0.7688 (3)0.0650 (13)
C220.7713 (4)0.8984 (4)0.8566 (5)0.080 (2)
H22A0.80120.85650.87360.096*
H22B0.75010.90690.90280.096*
C230.8234 (4)0.9543 (4)0.8587 (6)0.121 (3)
H23A0.83290.95340.80280.145*
H23B0.87190.94950.91210.145*
H23C0.79960.99690.86240.145*
H5A0.607 (3)0.848 (3)0.748 (5)0.12 (3)*
H5B0.574 (3)0.7883 (17)0.766 (3)0.032 (18)*
H6O0.729 (4)0.867 (3)0.740 (4)0.09 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.0233 (4)0.0278 (4)0.0377 (4)0.0029 (3)0.0119 (3)0.0007 (4)
Br10.0341 (4)0.1113 (7)0.0764 (5)0.0145 (4)0.0221 (4)0.0032 (5)
Br20.1617 (10)0.0646 (6)0.1296 (8)0.0721 (6)0.0491 (7)0.0051 (6)
S0.0293 (8)0.0399 (9)0.0426 (10)0.0052 (7)0.0176 (8)0.0051 (8)
O10.032 (2)0.042 (3)0.055 (3)0.0122 (19)0.024 (2)0.007 (2)
O20.038 (2)0.031 (2)0.054 (3)0.0071 (18)0.028 (2)0.0058 (19)
O30.029 (2)0.050 (3)0.065 (3)0.009 (2)0.006 (2)0.009 (2)
O40.058 (3)0.068 (3)0.044 (3)0.004 (2)0.027 (2)0.005 (2)
O50.035 (2)0.037 (3)0.036 (3)0.009 (2)0.013 (2)0.002 (2)
N10.027 (3)0.026 (3)0.052 (3)0.003 (2)0.016 (2)0.004 (2)
N20.026 (3)0.033 (3)0.045 (3)0.009 (2)0.015 (2)0.011 (3)
N30.021 (3)0.031 (3)0.047 (3)0.004 (2)0.012 (2)0.003 (3)
C10.033 (4)0.057 (4)0.033 (4)0.022 (3)0.010 (3)0.007 (3)
C20.038 (4)0.074 (5)0.036 (4)0.026 (4)0.015 (3)0.009 (4)
C30.065 (5)0.088 (6)0.055 (5)0.063 (5)0.022 (4)0.021 (5)
C40.099 (7)0.051 (5)0.076 (6)0.041 (5)0.040 (5)0.002 (4)
C50.069 (5)0.045 (4)0.057 (5)0.015 (4)0.020 (4)0.007 (4)
C60.044 (4)0.037 (4)0.047 (4)0.017 (3)0.021 (3)0.006 (3)
C70.047 (4)0.027 (3)0.044 (4)0.004 (3)0.015 (3)0.006 (3)
C80.032 (3)0.045 (4)0.078 (5)0.010 (3)0.026 (3)0.001 (4)
C90.038 (3)0.035 (3)0.064 (4)0.003 (3)0.031 (3)0.015 (4)
C100.043 (4)0.040 (4)0.054 (4)0.006 (3)0.019 (3)0.000 (4)
C110.056 (4)0.070 (5)0.044 (4)0.011 (4)0.016 (4)0.021 (4)
C120.047 (4)0.078 (6)0.052 (5)0.011 (4)0.015 (4)0.000 (4)
C130.022 (3)0.058 (5)0.047 (5)0.001 (3)0.002 (3)0.012 (4)
C140.050 (5)0.093 (6)0.042 (5)0.005 (5)0.003 (4)0.013 (5)
C150.045 (4)0.064 (5)0.076 (6)0.020 (4)0.006 (4)0.037 (5)
C160.039 (4)0.050 (4)0.042 (4)0.006 (3)0.014 (3)0.006 (4)
C170.037 (4)0.044 (4)0.087 (6)0.017 (3)0.017 (4)0.025 (4)
C180.057 (4)0.034 (4)0.074 (5)0.010 (3)0.026 (4)0.009 (4)
C190.052 (4)0.039 (4)0.055 (4)0.004 (3)0.020 (4)0.008 (4)
C200.013 (3)0.042 (4)0.037 (4)0.000 (3)0.004 (3)0.004 (3)
C210.011 (3)0.049 (4)0.037 (4)0.005 (3)0.003 (3)0.008 (3)
O60.054 (3)0.080 (4)0.056 (3)0.021 (3)0.017 (3)0.015 (3)
C220.057 (5)0.090 (6)0.074 (6)0.016 (5)0.008 (5)0.009 (5)
C230.079 (6)0.132 (8)0.106 (7)0.030 (6)0.009 (6)0.021 (6)
Geometric parameters (Å, º) top
Ni—O12.007 (3)C8—H8A0.9700
Ni—N12.058 (4)C8—H8B0.9700
Ni—O52.070 (4)C9—H9A0.9700
Ni—O22.096 (3)C9—H9B0.9700
Ni—N32.104 (4)C10—C111.385 (7)
Ni—N22.109 (4)C10—H100.9300
Br1—C21.907 (6)C11—C121.339 (8)
Br2—C41.884 (7)C11—H110.9300
S—O41.438 (4)C12—C131.401 (8)
S—O31.447 (4)C12—H120.9300
S—O21.473 (3)C13—C211.388 (7)
S—C91.765 (5)C13—C141.433 (8)
O1—C11.301 (6)C14—C151.361 (8)
O5—H5A0.82 (7)C14—H140.9300
O5—H5B0.81 (4)C15—C161.431 (8)
N1—C71.271 (6)C15—H150.9300
N1—C81.465 (6)C16—C201.386 (7)
N2—C101.319 (6)C16—C171.412 (8)
N2—C211.366 (6)C17—C181.349 (8)
N3—C191.327 (6)C17—H170.9300
N3—C201.356 (6)C18—C191.385 (8)
C1—C21.407 (7)C18—H180.9300
C1—C61.424 (8)C19—H190.9300
C2—C31.358 (8)C20—C211.435 (7)
C3—C41.377 (9)O6—C221.403 (7)
C3—H30.9300O6—H6O0.82 (7)
C4—C51.361 (9)C22—C231.459 (9)
C5—C61.405 (7)C22—H22A0.9700
C5—H50.9300C22—H22B0.9700
C6—C71.452 (7)C23—H23A0.9600
C7—H70.9300C23—H23B0.9600
C8—C91.512 (7)C23—H23C0.9600
O1—Ni—N190.79 (16)N1—C8—H8B109.1
O1—Ni—O590.08 (16)C9—C8—H8B109.1
N1—Ni—O594.54 (17)H8A—C8—H8B107.8
O1—Ni—O2175.06 (14)C8—C9—S112.2 (4)
N1—Ni—O292.40 (15)C8—C9—H9A109.2
O5—Ni—O285.90 (16)S—C9—H9A109.2
O1—Ni—N393.85 (15)C8—C9—H9B109.2
N1—Ni—N3172.77 (18)S—C9—H9B109.2
O5—Ni—N390.99 (18)H9A—C9—H9B107.9
O2—Ni—N383.35 (14)N2—C10—C11123.2 (6)
O1—Ni—N295.51 (15)N2—C10—H10118.4
N1—Ni—N294.85 (17)C11—C10—H10118.4
O5—Ni—N2168.99 (17)C12—C11—C10120.8 (7)
O2—Ni—N287.98 (14)C12—C11—H11119.6
N3—Ni—N279.20 (18)C10—C11—H11119.6
O4—S—O3114.4 (2)C11—C12—C13118.0 (6)
O4—S—O2112.2 (2)C11—C12—H12121.0
O3—S—O2110.8 (2)C13—C12—H12121.0
O4—S—C9107.0 (3)C21—C13—C12118.7 (6)
O3—S—C9105.6 (2)C21—C13—C14118.2 (6)
O2—S—C9106.3 (2)C12—C13—C14123.1 (6)
C1—O1—Ni125.4 (4)C15—C14—C13121.6 (6)
S—O2—Ni133.4 (2)C15—C14—H14119.2
Ni—O5—H5A126 (5)C13—C14—H14119.2
Ni—O5—H5B108 (3)C14—C15—C16119.8 (6)
H5A—O5—H5B119 (6)C14—C15—H15120.1
C7—N1—C8116.7 (5)C16—C15—H15120.1
C7—N1—Ni122.7 (4)C20—C16—C17117.0 (6)
C8—N1—Ni120.5 (3)C20—C16—C15120.2 (6)
C10—N2—C21116.8 (5)C17—C16—C15122.8 (6)
C10—N2—Ni130.7 (4)C18—C17—C16119.2 (6)
C21—N2—Ni112.1 (4)C18—C17—H17120.4
C19—N3—C20119.0 (5)C16—C17—H17120.4
C19—N3—Ni128.6 (4)C17—C18—C19120.9 (6)
C20—N3—Ni111.6 (4)C17—C18—H18119.5
O1—C1—C2121.8 (6)C19—C18—H18119.5
O1—C1—C6124.3 (5)N3—C19—C18121.1 (6)
C2—C1—C6113.8 (6)N3—C19—H19119.4
C3—C2—C1123.9 (7)C18—C19—H19119.4
C3—C2—Br1118.5 (5)N3—C20—C16122.8 (5)
C1—C2—Br1117.6 (5)N3—C20—C21118.2 (5)
C2—C3—C4120.9 (6)C16—C20—C21119.0 (5)
C2—C3—H3119.5N2—C21—C13122.4 (6)
C4—C3—H3119.5N2—C21—C20116.5 (5)
C5—C4—C3118.9 (6)C13—C21—C20121.1 (6)
C5—C4—Br2122.0 (7)C22—O6—H6O104 (5)
C3—C4—Br2119.2 (6)O6—C22—C23112.8 (6)
C4—C5—C6120.8 (7)O6—C22—H22A109.0
C4—C5—H5119.6C23—C22—H22A109.0
C6—C5—H5119.6O6—C22—H22B109.0
C5—C6—C1121.7 (6)C23—C22—H22B109.0
C5—C6—C7115.5 (6)H22A—C22—H22B107.8
C1—C6—C7122.8 (5)C22—C23—H23A109.5
N1—C7—C6128.7 (5)C22—C23—H23B109.5
N1—C7—H7115.6H23A—C23—H23B109.5
C6—C7—H7115.6C22—C23—H23C109.5
N1—C8—C9112.5 (5)H23A—C23—H23C109.5
N1—C8—H8A109.1H23B—C23—H23C109.5
C9—C8—H8A109.1
N1—Ni—O1—C125.1 (4)O1—C1—C6—C5179.3 (6)
O5—Ni—O1—C1119.6 (4)C2—C1—C6—C51.9 (8)
N3—Ni—O1—C1149.4 (4)O1—C1—C6—C72.8 (9)
N2—Ni—O1—C169.9 (4)C2—C1—C6—C7179.8 (5)
O4—S—O2—Ni120.9 (3)C8—N1—C7—C6178.5 (5)
O3—S—O2—Ni109.9 (3)Ni—N1—C7—C60.6 (8)
C9—S—O2—Ni4.3 (4)C5—C6—C7—N1168.5 (6)
N1—Ni—O2—S15.3 (3)C1—C6—C7—N19.5 (10)
O5—Ni—O2—S109.7 (3)C7—N1—C8—C9125.1 (5)
N3—Ni—O2—S158.9 (3)Ni—N1—C8—C952.9 (6)
N2—Ni—O2—S79.5 (3)N1—C8—C9—S81.1 (5)
O1—Ni—N1—C713.7 (5)O4—S—C9—C8172.2 (4)
O5—Ni—N1—C7103.9 (5)O3—S—C9—C865.5 (4)
O2—Ni—N1—C7170.0 (4)O2—S—C9—C852.2 (4)
N2—Ni—N1—C781.9 (5)C21—N2—C10—C112.7 (8)
O1—Ni—N1—C8168.4 (4)Ni—N2—C10—C11169.2 (4)
O5—Ni—N1—C878.2 (4)N2—C10—C11—C120.1 (9)
O2—Ni—N1—C87.8 (4)C10—C11—C12—C130.9 (10)
N2—Ni—N1—C896.0 (4)C11—C12—C13—C210.6 (9)
O1—Ni—N2—C1082.2 (5)C11—C12—C13—C14179.1 (6)
N1—Ni—N2—C109.1 (5)C21—C13—C14—C150.6 (9)
O5—Ni—N2—C10157.6 (7)C12—C13—C14—C15177.9 (6)
O2—Ni—N2—C10101.3 (5)C13—C14—C15—C161.8 (10)
N3—Ni—N2—C10175.0 (5)C14—C15—C16—C204.0 (9)
O1—Ni—N2—C21105.6 (3)C14—C15—C16—C17177.8 (6)
N1—Ni—N2—C21163.1 (3)C20—C16—C17—C181.5 (9)
O5—Ni—N2—C2114.6 (10)C15—C16—C17—C18179.8 (6)
O2—Ni—N2—C2170.9 (3)C16—C17—C18—C191.6 (9)
N3—Ni—N2—C2112.8 (3)C20—N3—C19—C180.4 (8)
O1—Ni—N3—C1982.6 (5)Ni—N3—C19—C18167.6 (4)
O5—Ni—N3—C197.5 (5)C17—C18—C19—N30.6 (9)
O2—Ni—N3—C1993.3 (5)C19—N3—C20—C160.4 (8)
N2—Ni—N3—C19177.5 (5)Ni—N3—C20—C16169.6 (4)
O1—Ni—N3—C20108.6 (3)C19—N3—C20—C21177.1 (5)
O5—Ni—N3—C20161.3 (3)Ni—N3—C20—C2113.0 (5)
O2—Ni—N3—C2075.5 (3)C17—C16—C20—N30.5 (8)
N2—Ni—N3—C2013.7 (3)C15—C16—C20—N3178.8 (5)
Ni—O1—C1—C2159.5 (4)C17—C16—C20—C21178.0 (5)
Ni—O1—C1—C623.3 (8)C15—C16—C20—C213.7 (8)
O1—C1—C2—C3179.3 (6)C10—N2—C21—C134.3 (7)
C6—C1—C2—C31.9 (9)Ni—N2—C21—C13169.1 (4)
O1—C1—C2—Br13.1 (7)C10—N2—C21—C20176.7 (4)
C6—C1—C2—Br1179.4 (4)Ni—N2—C21—C2010.0 (5)
C1—C2—C3—C40.2 (11)C12—C13—C21—N23.3 (8)
Br1—C2—C3—C4177.7 (5)C14—C13—C21—N2178.1 (5)
C2—C3—C4—C51.6 (11)C12—C13—C21—C20177.7 (5)
C2—C3—C4—Br2178.5 (5)C14—C13—C21—C200.9 (8)
C3—C4—C5—C61.5 (11)N3—C20—C21—N22.1 (7)
Br2—C4—C5—C6178.6 (5)C16—C20—C21—N2179.6 (5)
C4—C5—C6—C10.3 (10)N3—C20—C21—C13178.9 (5)
C4—C5—C6—C7178.3 (6)C16—C20—C21—C131.3 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O60.82 (7)1.99 (6)2.759 (7)156 (6)
O5—H5B···O1i0.81 (4)1.98 (4)2.767 (5)162 (5)
O6—H6O···O30.82 (7)2.05 (6)2.828 (7)157 (6)
Symmetry code: (i) x+1, y, z+3/2.
 

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