Tetra­aqua­[3-oxo-1,3-bis­(pyridinium-2-yl)propan-1-olato]nickel(II) tribromide dihydrate (2024)

Table of Contents
Supporting information Key indicators checkCIF/PLATON results References

Tetra­aqua­[3-oxo-1,3-bis­(pyridinium-2-yl)propan-1-olato]nickel(II) tribromide dihydrate (26)

B. L. Westcott, G. Crundwell and N. L. Alicea-Velázquez

The reaction of 1,3-dipyridyl-1,2-propane-1,3-dione (dppo) with nickel(II) bromide in HBr-acidified methanol produces a bromide salt containing the [(C13H11N2O2)(H2O)4Ni]+3 cation. The ligand is in its enol form— the O atoms bond to the nickel whereas the pyridyl N atoms are protonated as pyridinium rings. The nickel completes its octa­hedral coordinatin sphere by binding four waters. Three bromides balance the charge of the cation and there are two waters of hydration. The mean plane of the flat ligand makes an angle of 19.480 (17)° with respect to the plane defined by the nickel and its four equatorial O atoms. There is exstensive hydrogen bonding involving the anions, waters, and pyridinium N atoms.

Keywords: crystal structure; di­pyridyl­propane­dione; pyridinium; nickel.

ReadarticleSimilararticles

Supporting information

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698902000081X/zl2768sup1.cif
Contains datablock I

Structure factor file (CIF format) https://doi.org/10.1107/S205698902000081X/zl2768Isup2.hkl
Contains datablock I

Portable Document Format (PDF) file https://doi.org/10.1107/S205698902000081X/zl2768sup3.pdf
IR spectrum of NI(dppo)

CCDC reference: 1979583

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean Tetra­aqua­[3-oxo-1,3-bis­(pyridinium-2-yl)propan-1-olato]nickel(II) tribromide dihydrate (32)(C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.125
  • Data-to-parameter ratio = 28.5

checkCIF/PLATON results

No syntax errors foundTetra­aqua­[3-oxo-1,3-bis­(pyridinium-2-yl)propan-1-olato]nickel(II) tribromide dihydrate (33)Alert level BPLAT420_ALERT_2_B D-H Without Acceptor O8 --H8A . Please CheckPLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min). 21 NoteTetra­aqua­[3-oxo-1,3-bis­(pyridinium-2-yl)propan-1-olato]nickel(II) tribromide dihydrate (34)Alert level CPLAT222_ALERT_3_C NonSolvent Resd 1 H Uiso(max)/Uiso(min) Range 6.1 RatioPLAT230_ALERT_2_C Hirshfeld Test Diff for N2 --C9 . 6.5 s.u.PLAT260_ALERT_2_C Large Average Ueq of Residue Including O8 0.106 CheckPLAT420_ALERT_2_C D-H Without Acceptor N1 --H1 . Please CheckPLAT420_ALERT_2_C D-H Without Acceptor N2 --H2 . Please CheckPLAT480_ALERT_4_C Long H...A H-Bond Reported H1 ..BR1 . 2.94 Ang.PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 ..BR1 . 3.02 Ang.PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A ..BR3 . 3.06 Ang.PLAT481_ALERT_4_C Long D...A H-Bond Reported O8 ..BR3 3.88 Ang.PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.299 CheckPLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 6 ReportTetra­aqua­[3-oxo-1,3-bis­(pyridinium-2-yl)propan-1-olato]nickel(II) tribromide dihydrate (35)Alert level GPLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 18 NotePLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 ReportPLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 2 ReportPLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 CheckPLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 CheckPLAT432_ALERT_2_G Short Inter X...Y Contact Br2 ..C10 3.31 Ang. x,y,-1+z = 1_554 CheckPLAT432_ALERT_2_G Short Inter X...Y Contact Br3 ..C4 3.33 Ang. 1-x,1-y,1-z = 3_666 CheckPLAT794_ALERT_5_G Tentative Bond Valency for Ni1 (II) . 2.07 InfoPLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 12 NotePLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 744 NotePLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 NotePLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 6 NotePLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 2 Info 0 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 11 ALERT level C = Check. Ensure it is not caused by an omission or oversight 13 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) andMercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Bourhis et al., 2015).

Tetraaqua[3-oxo-1,3-bis(pyridinium-2-yl)propan-1-olato]nickel(II) tribromidedihydrate top

Crystal data

top

[Ni(C13H11N2O2)(H2O)4]3Br·2H2OF(000) = 1248
Mr = 633.77Dx = 1.922 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.8071 (6) ÅCell parameters from 4741 reflections
b = 23.8031 (16) Åθ = 4.6–32.1°
c = 13.6302 (10) ŵ = 6.40 mm−1
β = 97.476 (9)°T = 293 K
V = 2189.7 (3) Å3Block, orange
Z = 40.32 × 0.28 × 0.19 mm

Data collection

top

Agilent Xcalibur Sapphire3
diffractometer		7970 independent reflections
Radiation source: Enhance (Mo) X-ray Source5803 reflections with I > 2σ(I)
Detector resolution: 16.1790 pixels mm-1Rint = 0.034
ω scansθmax = 33.7°, θmin = 4.3°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		h = −10→10
Tmin = 0.503, Tmax = 1.000k = −36→36
26929 measured reflectionsl = −20→21

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: mixed
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0561P)2 + 2.3402P]
where P = (Fo2 + 2Fc2)/3
7970 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 1.10 e Å−3
12 restraintsΔρmin = −1.39 e Å−3

Special details

top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

top

xyzUiso*/Ueq
Br10.28363 (5)0.60904 (2)0.46388 (3)0.04291 (10)
Br20.22784 (5)0.48206 (2)0.10507 (2)0.03503 (9)
Br30.80885 (8)0.76767 (2)0.39510 (3)0.05624 (13)
Ni10.15038 (6)0.37164 (2)0.81987 (3)0.02833 (10)
O10.2089 (4)0.37484 (8)0.67975 (15)0.0311 (4)
O20.2542 (4)0.45031 (9)0.83901 (15)0.0318 (5)
O30.0917 (5)0.37407 (10)0.96216 (18)0.0439 (6)
O40.0286 (4)0.29148 (10)0.79662 (19)0.0417 (6)
O50.4287 (5)0.33525 (12)0.8585 (2)0.0489 (6)
O6−0.1333 (4)0.40312 (11)0.77851 (19)0.0414 (5)
N10.2313 (5)0.45128 (15)0.4508 (2)0.0488 (8)
H10.24370.48620.46690.059*
N20.3028 (5)0.59168 (13)0.7459 (2)0.0473 (7)
H20.30170.58820.68310.057*
C10.2240 (6)0.43458 (18)0.3530 (2)0.0464 (9)
H1A0.23120.46150.30410.056*
C20.2062 (7)0.37877 (18)0.3273 (2)0.0480 (9)
H2A0.20290.36770.26170.058*
C30.1935 (6)0.33996 (17)0.3999 (2)0.0432 (8)
H30.18140.30200.38410.052*
C40.1984 (4)0.35680 (12)0.49387 (18)0.0241 (5)
H40.18740.32970.54200.029*
C50.2182 (4)0.41042 (12)0.52228 (19)0.0267 (5)
C60.2239 (5)0.41925 (12)0.6312 (2)0.0267 (5)
C70.2441 (5)0.47393 (12)0.6692 (2)0.0300 (6)
H70.24770.50370.62540.036*
C80.2593 (4)0.48545 (11)0.7704 (2)0.0264 (5)
C90.2832 (4)0.54534 (11)0.8042 (2)0.0246 (5)
C100.2865 (4)0.55252 (11)0.90202 (18)0.0216 (5)
H100.27010.52110.94080.026*
C110.3121 (6)0.60228 (14)0.9464 (3)0.0387 (7)
H110.31700.60511.01480.046*
C120.3313 (6)0.64942 (15)0.8900 (3)0.0469 (9)
H120.34900.68450.91980.056*
C130.3243 (6)0.64421 (14)0.7904 (3)0.0450 (8)
H130.33390.67600.75170.054*
O70.6193 (5)0.29510 (15)0.7017 (3)0.0586 (8)
O80.6929 (11)0.2404 (2)0.9388 (4)0.1057 (17)
H3A0.120 (13)0.4061 (18)0.986 (6)0.159*
H3B0.140 (12)0.349 (3)1.000 (5)0.159*
H4A−0.095 (3)0.289 (4)0.791 (7)0.159*
H4B0.061 (14)0.272 (3)0.752 (5)0.159*
H5A0.489 (13)0.317 (4)0.818 (6)0.159*
H5B0.448 (15)0.304 (2)0.886 (7)0.159*
H6A−0.169 (13)0.402 (4)0.7173 (18)0.159*
H6B−0.178 (13)0.432 (2)0.802 (7)0.159*
H7A0.592 (15)0.319 (3)0.656 (5)0.159*
H7B0.513 (8)0.281 (4)0.673 (7)0.159*
H8A0.789 (10)0.252 (4)0.980 (6)0.159*
H8B0.658 (15)0.2068 (16)0.945 (8)0.159*

Atomic displacement parameters (Å2)

top

U11U22U33U12U13U23
Br10.03826 (18)0.0478 (2)0.04137 (18)−0.00130 (14)0.00006 (14)0.00498 (15)
Br20.04109 (18)0.04094 (18)0.02300 (13)0.00484 (13)0.00390 (12)−0.00060 (11)
Br30.0857 (3)0.02834 (17)0.0548 (2)−0.00371 (17)0.0097 (2)−0.01026 (15)
Ni10.0437 (2)0.02121 (17)0.02022 (16)−0.00070 (14)0.00474 (15)0.00139 (12)
O10.0497 (13)0.0228 (9)0.0210 (9)0.0008 (9)0.0051 (9)0.0011 (7)
O20.0510 (13)0.0230 (9)0.0213 (9)−0.0049 (9)0.0038 (9)0.0000 (7)
O30.0761 (19)0.0318 (12)0.0258 (10)−0.0031 (12)0.0139 (12)0.0026 (9)
O40.0597 (16)0.0247 (10)0.0418 (13)−0.0045 (11)0.0105 (12)−0.0001 (9)
O50.0583 (17)0.0447 (15)0.0407 (13)0.0133 (13)−0.0053 (12)0.0019 (11)
O60.0482 (14)0.0358 (12)0.0392 (12)0.0026 (11)0.0021 (11)−0.0038 (10)
N10.064 (2)0.0480 (18)0.0351 (15)0.0050 (16)0.0085 (15)0.0064 (13)
N20.064 (2)0.0373 (15)0.0405 (15)−0.0065 (15)0.0061 (15)−0.0003 (13)
C10.061 (2)0.055 (2)0.0230 (13)0.0033 (18)0.0076 (15)0.0093 (14)
C20.058 (2)0.066 (3)0.0200 (13)0.0027 (19)0.0057 (15)−0.0077 (14)
C30.054 (2)0.0456 (19)0.0301 (15)−0.0022 (16)0.0045 (15)−0.0164 (14)
C40.0314 (13)0.0240 (11)0.0170 (10)−0.0010 (10)0.0033 (10)−0.0048 (9)
C50.0314 (14)0.0292 (13)0.0193 (10)0.0021 (11)0.0029 (10)−0.0013 (10)
C60.0349 (14)0.0250 (12)0.0201 (10)0.0019 (11)0.0038 (10)0.0000 (9)
C70.0476 (17)0.0219 (12)0.0204 (11)−0.0025 (11)0.0040 (12)0.0018 (9)
C80.0341 (14)0.0219 (11)0.0227 (11)−0.0020 (10)0.0021 (11)−0.0011 (9)
C90.0275 (12)0.0226 (12)0.0232 (11)−0.0021 (10)0.0022 (10)−0.0023 (9)
C100.0260 (12)0.0190 (11)0.0202 (10)−0.0032 (9)0.0052 (9)−0.0035 (8)
C110.0496 (19)0.0339 (16)0.0346 (15)−0.0085 (14)0.0135 (15)−0.0141 (13)
C120.062 (2)0.0276 (16)0.053 (2)−0.0092 (15)0.0142 (18)−0.0108 (14)
C130.065 (2)0.0242 (14)0.0465 (19)−0.0097 (15)0.0092 (18)0.0011 (14)
O70.0591 (18)0.0536 (18)0.0612 (19)0.0006 (14)0.0002 (15)0.0041 (14)
O80.161 (5)0.071 (3)0.086 (3)0.024 (3)0.020 (3)0.020 (3)

Geometric parameters (Å, º)

top

Ni1—O12.003 (2)C2—C31.365 (6)
Ni1—O22.006 (2)C2—H2A0.9300
Ni1—O32.031 (2)C3—C41.339 (4)
Ni1—O62.080 (3)C3—H30.9300
Ni1—O52.088 (3)C4—C51.336 (4)
Ni1—O42.088 (2)C4—H40.9300
O1—C61.258 (3)C5—C61.495 (4)
O2—C81.259 (3)C6—C71.401 (4)
O3—H3A0.84 (2)C7—C81.396 (4)
O3—H3B0.83 (2)C7—H70.9300
O4—H4A0.84 (2)C8—C91.501 (4)
O4—H4B0.82 (2)C9—C101.341 (3)
O5—H5A0.84 (2)C10—C111.331 (4)
O5—H5B0.84 (2)C10—H100.9300
O6—H6A0.84 (2)C11—C121.376 (5)
O6—H6B0.83 (2)C11—H110.9300
N1—C11.386 (5)C12—C131.358 (5)
N1—C51.387 (4)C12—H120.9300
N1—H10.8600C13—H130.9300
N2—C91.376 (4)O7—H7A0.84 (2)
N2—C131.389 (5)O7—H7B0.85 (2)
N2—H20.8600O8—H8A0.85 (2)
C1—C21.375 (6)O8—H8B0.84 (2)
C1—H1A0.9300
O1—Ni1—O288.75 (9)C3—C2—C1118.7 (3)
O1—Ni1—O3176.19 (9)C3—C2—H2A120.6
O2—Ni1—O387.65 (9)C1—C2—H2A120.6
O1—Ni1—O691.18 (10)C4—C3—C2119.7 (3)
O2—Ni1—O689.88 (10)C4—C3—H3120.2
O3—Ni1—O687.57 (12)C2—C3—H3120.2
O1—Ni1—O588.26 (11)C5—C4—C3123.5 (3)
O2—Ni1—O593.54 (11)C5—C4—H4118.2
O3—Ni1—O593.21 (12)C3—C4—H4118.2
O6—Ni1—O5176.52 (11)C4—C5—N1118.7 (3)
O1—Ni1—O490.82 (9)C4—C5—C6114.3 (2)
O2—Ni1—O4177.08 (11)N1—C5—C6127.1 (3)
O3—Ni1—O492.72 (10)O1—C6—C7126.6 (3)
O6—Ni1—O487.24 (11)O1—C6—C5114.3 (2)
O5—Ni1—O489.34 (12)C7—C6—C5119.1 (2)
C6—O1—Ni1124.99 (19)C8—C7—C6122.6 (3)
C8—O2—Ni1124.54 (18)C8—C7—H7118.7
Ni1—O3—H3A109 (6)C6—C7—H7118.7
Ni1—O3—H3B117 (6)O2—C8—C7126.7 (3)
H3A—O3—H3B112 (9)O2—C8—C9114.5 (2)
Ni1—O4—H4A118 (7)C7—C8—C9118.8 (2)
Ni1—O4—H4B120 (7)C10—C9—N2118.8 (3)
H4A—O4—H4B104 (8)C10—C9—C8114.5 (2)
Ni1—O5—H5A123 (7)N2—C9—C8126.8 (3)
Ni1—O5—H5B124 (7)C11—C10—C9123.3 (3)
H5A—O5—H5B77 (8)C11—C10—H10118.3
Ni1—O6—H6A114 (6)C9—C10—H10118.3
Ni1—O6—H6B125 (7)C10—C11—C12119.2 (3)
H6A—O6—H6B109 (8)C10—C11—H11120.4
C1—N1—C5118.5 (3)C12—C11—H11120.4
C1—N1—H1120.8C13—C12—C11119.4 (3)
C5—N1—H1120.8C13—C12—H12120.3
C9—N2—C13118.8 (3)C11—C12—H12120.3
C9—N2—H2120.6C12—C13—N2120.4 (3)
C13—N2—H2120.6C12—C13—H13119.8
C2—C1—N1120.9 (3)N2—C13—H13119.8
C2—C1—H1A119.5H7A—O7—H7B80 (8)
N1—C1—H1A119.5H8A—O8—H8B116 (10)

Hydrogen-bond geometry (Å, º)

top

D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.862.943.774 (4)165
N2—H2···Br10.863.023.852 (3)165
C1—H1A···Br20.932.753.567 (3)147
C4—H4···Br3i0.932.473.330 (3)154
C10—H10···Br2ii0.932.483.305 (3)149
O3—H3A···Br2ii0.84 (2)2.48 (4)3.285 (3)161 (9)
O3—H3B···Br3iii0.83 (2)2.40 (3)3.212 (2)165 (8)
O4—H4A···O7iv0.84 (2)2.16 (5)2.917 (4)150 (9)
O4—H4B···Br3i0.82 (2)2.48 (3)3.284 (3)167 (9)
O5—H5A···O70.84 (2)1.99 (3)2.808 (5)163 (10)
O5—H5B···O80.84 (2)2.29 (6)3.002 (6)142 (9)
O6—H6A···Br1v0.84 (2)2.51 (2)3.342 (3)175 (9)
O6—H6B···Br2v0.83 (2)2.45 (3)3.266 (3)165 (9)
O7—H7A···Br1i0.84 (2)2.59 (6)3.335 (4)149 (9)
O7—H7B···Br3i0.85 (2)2.54 (2)3.386 (3)173 (9)
O8—H8A···Br3vi0.85 (2)3.06 (3)3.880 (7)165 (9)
O8—H8B···Br1iii0.84 (2)2.65 (6)3.393 (5)149 (9)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, y−1/2, −z+3/2; (iv) x−1, y, z; (v) −x, −y+1, −z+1; (vi) −x+2, y−1/2, −z+3/2.


Tetra­aqua­[3-oxo-1,3-bis­(pyridinium-2-yl)propan-1-olato]nickel(II) tribromide dihydrate (2024)

References

Top Articles
Homemade Caramels ~ An Easy and Favorite Holiday Candy Recipe
Healthy Gummy Bear Recipe (Using Fruit & Honey)
Team Umizoomi The Ghost Family Costume Party Dailymotion
ARK: Survival Ascended PVP | 20x tek auto turret | ID 212433546 | PlayerAuctions
FAQs | Tickets For Less
Kansas City Chiefs Tickets
Get Started with Canvas @ USD
Canvas Launching Spring 2024
Merry-Go-Round (1956) Out now from Second Run - REVIEW
‘Anyone can go out and spend $1 billion. The trick is getting a good return for your investors.’ - Music Business Worldwide [STAGING]
37 workers at state-run developmental center targeted in PPP fraud probe
Ludeman Center in Park Forest, site of state’s largest long-term care facility COVID-19 outbreak, names new interim director
Latest Posts
Eggnog Recipe - How to Make Homemade Eggnog
How to Convert Slow Cooker Recipes for the Instant Pot
Article information

Author: Allyn Kozey

Last Updated:

Views: 5864

Rating: 4.2 / 5 (63 voted)

Reviews: 86% of readers found this page helpful

Author information

Name: Allyn Kozey

Birthday: 1993-12-21

Address: Suite 454 40343 Larson Union, Port Melia, TX 16164

Phone: +2456904400762

Job: Investor Administrator

Hobby: Sketching, Puzzles, Pet, Mountaineering, Skydiving, Dowsing, Sports

Introduction: My name is Allyn Kozey, I am a outstanding, colorful, adventurous, encouraging, zealous, tender, helpful person who loves writing and wants to share my knowledge and understanding with you.