Literature DB >> 21754270

Yttrium ethyl-enediammonium squarate tetra-hydrate.

Louiza Zenkhri, Nathalie Audebrand, Thierry Bataille.   

Abstract

The title compound, {(C(2)H(10)N(2))(1.5)[Y(C(4)O(4))(3)(H(2)O)(4)]}(n) {system-atic name: catena-poly[sesqui(ethyl-enediammonium) [[tetra-aquabis-(squarato-κO)yttrium(III)]-μ-squarato-κ(2)O:O']]}, was synthesized by slow evaporation of an acid solution. The asymetric unit contains one yttrium cation in an anti-prismatic environnement, three squarate groups, one and a half protonated ethyl-enediamine mol-ecules and four water mol-ecules. YO(8) polyhedra are connected through bis-(mono-dentate) squarates, leading to infinite zigzag chains, in between which are located ammonium groups. A framework of hydrogen bonds between protonated amine N atoms, water mol-ecules and squarate anions ensures the cohesion of the structure.

Entities:  

Year:  2011        PMID: 21754270      PMCID: PMC3089218          DOI: 10.1107/S1600536811011251

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For a related structure, see: Kazerouni et al. (1994) ▶. The title compound was obtained together with two polymorphs of (C2H10N2)(HC4O4)2(H2O) (Mathew et al., 2002 ▶; Zenkhri et al., 2011) ▶. For related yttrium squarates with potassium, see: Mahé & Bataille (2004 ▶).

Experimental

Crystal data

(C2H10N2)1.5[Y(C4O4)3(H2O)4] M = 590.27 Monoclinic, a = 8.9780 (2) Å b = 13.2864 (3) Å c = 18.3970 (4) Å β = 90.935 (1)° V = 2194.20 (8) Å3 Z = 4 Mo Kα radiation μ = 2.75 mm−1 T = 293 K 0.22 × 0.14 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: analytical (de Meulenaer & Tompa, 1965) ▶ T min = 0.583, T max = 0.734 23285 measured reflections 5016 independent reflections 4140 reflections with I > 2σ(I) R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.103 S = 1.10 5016 reflections 316 parameters H-atom parameters constrained Δρmax = 1.77 e Å−3 Δρmin = −0.62 e Å−3 Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DIRAX/LSQ (Duisenberg, 1992 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011251/ru2003sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011251/ru2003Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
(C2H10N2)1.5[Y(C4O4)3(H2O)4]F(000) = 1204
Mr = 590.27Dx = 1.787 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.9780 (2) ÅCell parameters from 57148 reflections
b = 13.2864 (3) Åθ = 2.9–27.5°
c = 18.3970 (4) ŵ = 2.75 mm1
β = 90.935 (1)°T = 293 K
V = 2194.20 (8) Å3Prism, colourless
Z = 40.22 × 0.14 × 0.12 mm
Nonius KappaCCD diffractometer5016 independent reflections
Radiation source: fine-focus sealed tube4140 reflections with I > 2σ(I)
horizonally mounted graphite crystalRint = 0.065
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 2.9°
CCD scansh = −11→11
Absorption correction: analytical (de Meulenaer & Tompa, 1965)k = −17→17
Tmin = 0.583, Tmax = 0.734l = −23→23
23285 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0368P)2 + 4.9093P] where P = (Fo2 + 2Fc2)/3
5016 reflections(Δ/σ)max = 0.002
316 parametersΔρmax = 1.77 e Å3
0 restraintsΔρmin = −0.62 e Å3
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 > 2σ(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.
xyzUiso*/Ueq
Y10.81967 (3)0.09385 (2)0.775395 (16)0.01739 (9)
OW10.6982 (2)−0.02399 (18)0.69447 (13)0.0255 (5)
H9110.6156−0.06260.70850.038*
H9120.7647−0.07200.67850.038*
OW20.5760 (3)0.15385 (18)0.74497 (16)0.0332 (6)
H9210.47740.13030.74460.050*
H9220.55680.22160.75500.050*
OW30.7609 (4)0.1825 (2)0.88343 (19)0.0653 (12)
H9310.78800.23760.91160.098*
H9320.73450.14470.92430.098*
OW41.0544 (3)0.16009 (19)0.82212 (15)0.0332 (6)
H9411.14510.14380.80130.050*
H9421.06230.22670.83560.050*
C10.3965 (4)−0.0751 (3)0.9370 (2)0.0344 (9)
O10.2824 (3)−0.0919 (3)0.97182 (19)0.0618 (10)
C20.4625 (4)0.0166 (3)0.90558 (19)0.0308 (8)
O20.4298 (4)0.1078 (2)0.90299 (18)0.0567 (9)
C30.5884 (4)−0.0427 (2)0.88126 (17)0.0215 (6)
O30.7096 (2)−0.02378 (17)0.84855 (13)0.0260 (5)
C40.5259 (4)−0.1337 (3)0.91110 (19)0.0270 (7)
O40.5696 (3)−0.2235 (2)0.91517 (16)0.0389 (6)
C50.9863 (4)−0.0763 (2)0.60978 (17)0.0212 (6)
O50.8971 (3)−0.14412 (17)0.62986 (14)0.0283 (5)
C61.0043 (4)0.0306 (2)0.62387 (17)0.0212 (6)
O60.9443 (3)0.09575 (17)0.66401 (13)0.0278 (5)
C71.1316 (4)0.0349 (2)0.57414 (18)0.0228 (6)
O71.2148 (3)0.10214 (18)0.55251 (16)0.0356 (6)
C81.1158 (4)−0.0751 (2)0.56315 (18)0.0227 (7)
O81.1858 (3)−0.14202 (19)0.53033 (16)0.0368 (6)
C90.8814 (3)0.4399 (2)0.72880 (17)0.0190 (6)
O91.0131 (2)0.46219 (16)0.71244 (13)0.0244 (5)
C100.7446 (4)0.4939 (2)0.74815 (18)0.0225 (6)
O100.7095 (3)0.58392 (18)0.75490 (17)0.0360 (6)
C110.6683 (3)0.3960 (2)0.75669 (18)0.0216 (6)
O110.5417 (3)0.3661 (2)0.77318 (16)0.0351 (6)
C120.8066 (3)0.3451 (2)0.73838 (17)0.0203 (6)
O120.8488 (3)0.25554 (17)0.73267 (15)0.0316 (6)
N10.1150 (3)0.2173 (2)1.13530 (16)0.0276 (6)
H110.18630.25791.12300.033*
H120.15310.16151.15200.033*
H130.06180.24541.16880.033*
C130.0190 (4)0.1952 (3)1.0706 (2)0.0315 (8)
H131−0.01920.25811.05110.038*
H132−0.06540.15531.08580.038*
C140.0985 (4)0.1398 (3)1.0114 (2)0.0317 (8)
H1410.14880.08171.03230.038*
H1420.02570.11560.97600.038*
N20.2096 (3)0.2041 (2)0.97398 (16)0.0300 (7)
H210.27780.22781.01070.036*
H220.16070.25610.94770.036*
H230.26830.17170.94640.036*
N30.4125 (4)−0.4070 (3)0.93482 (18)0.0392 (8)
H310.4774−0.37790.90720.047*
H320.3940−0.36850.97180.047*
H330.3306−0.41750.91000.047*
C150.4730 (4)−0.5043 (3)0.9610 (2)0.0348 (9)
H1510.5550−0.52460.93060.042*
H1520.3963−0.55550.95740.042*
U11U22U33U12U13U23
Y10.01584 (14)0.01229 (13)0.02423 (15)0.00006 (11)0.00636 (10)0.00037 (12)
OW10.0212 (11)0.0241 (12)0.0313 (12)−0.0036 (9)0.0061 (9)−0.0030 (10)
OW20.0161 (11)0.0211 (12)0.0625 (18)0.0014 (9)0.0049 (11)0.0036 (12)
OW30.099 (3)0.0388 (17)0.060 (2)−0.0325 (18)0.055 (2)−0.0255 (15)
OW40.0302 (13)0.0235 (12)0.0456 (16)−0.0003 (10)−0.0048 (11)−0.0100 (11)
C10.0197 (16)0.058 (3)0.0259 (18)−0.0034 (16)0.0021 (13)0.0039 (16)
O10.0269 (15)0.104 (3)0.055 (2)−0.0107 (17)0.0177 (14)0.011 (2)
C20.0284 (18)0.042 (2)0.0228 (17)0.0099 (16)0.0066 (14)0.0032 (15)
O20.068 (2)0.0505 (19)0.0524 (19)0.0358 (17)0.0266 (17)0.0089 (15)
C30.0219 (15)0.0236 (16)0.0190 (15)0.0011 (13)0.0032 (12)0.0002 (12)
O30.0234 (11)0.0234 (12)0.0317 (13)0.0022 (9)0.0116 (10)0.0058 (10)
C40.0217 (16)0.0335 (18)0.0257 (17)−0.0081 (14)−0.0004 (13)0.0042 (14)
O40.0408 (15)0.0259 (13)0.0498 (17)−0.0086 (12)0.0008 (13)0.0090 (12)
C50.0258 (16)0.0155 (14)0.0224 (15)0.0002 (12)0.0017 (12)0.0011 (11)
O50.0297 (12)0.0183 (11)0.0373 (14)−0.0060 (10)0.0110 (10)−0.0002 (10)
C60.0249 (15)0.0158 (14)0.0232 (16)−0.0003 (12)0.0055 (12)0.0006 (12)
O60.0352 (13)0.0170 (11)0.0317 (13)−0.0019 (10)0.0166 (10)−0.0012 (10)
C70.0238 (16)0.0182 (15)0.0265 (16)0.0022 (12)0.0068 (13)0.0024 (12)
O70.0364 (14)0.0196 (12)0.0517 (16)−0.0027 (11)0.0238 (12)0.0033 (11)
C80.0243 (16)0.0182 (15)0.0258 (16)0.0005 (12)0.0025 (13)−0.0006 (12)
O80.0382 (14)0.0227 (13)0.0500 (17)0.0037 (11)0.0193 (12)−0.0081 (11)
C90.0183 (14)0.0160 (14)0.0229 (15)0.0008 (11)0.0034 (12)−0.0004 (12)
O90.0177 (11)0.0168 (11)0.0390 (14)−0.0030 (9)0.0086 (9)−0.0019 (10)
C100.0195 (15)0.0193 (15)0.0289 (17)0.0032 (12)0.0023 (12)−0.0001 (13)
O100.0253 (12)0.0161 (12)0.0668 (19)0.0064 (10)0.0064 (12)−0.0027 (12)
C110.0174 (14)0.0193 (15)0.0282 (16)0.0020 (12)0.0045 (12)0.0017 (13)
O110.0181 (11)0.0275 (13)0.0602 (18)0.0025 (10)0.0131 (11)0.0071 (12)
C120.0185 (14)0.0177 (14)0.0247 (16)0.0015 (12)0.0040 (12)0.0036 (12)
O120.0275 (12)0.0132 (11)0.0546 (16)0.0009 (9)0.0149 (11)0.0046 (11)
N10.0320 (15)0.0198 (13)0.0314 (16)0.0027 (12)0.0110 (12)0.0010 (12)
C130.0216 (16)0.0338 (19)0.039 (2)0.0014 (14)0.0029 (14)0.0051 (16)
C140.040 (2)0.0239 (17)0.0309 (19)0.0005 (15)−0.0044 (15)0.0000 (14)
N20.0353 (16)0.0283 (15)0.0267 (15)0.0109 (13)0.0061 (12)−0.0009 (12)
N30.0367 (18)0.046 (2)0.0351 (17)−0.0108 (16)0.0085 (14)−0.0034 (15)
C150.0296 (18)0.044 (2)0.031 (2)−0.0111 (16)0.0079 (15)−0.0092 (16)
Y1—O32.297 (2)C8—O81.250 (4)
Y1—O122.304 (2)C9—O91.261 (4)
Y1—O9i2.314 (2)C9—C121.439 (4)
Y1—O62.351 (2)C9—C101.471 (4)
Y1—OW32.377 (3)O9—Y1ii2.314 (2)
Y1—OW22.386 (2)C10—O101.244 (4)
Y1—OW12.409 (2)C10—C111.479 (4)
Y1—OW42.428 (2)C11—O111.247 (4)
OW1—H9110.9405C11—C121.458 (4)
OW1—H9120.9255C12—O121.254 (4)
OW2—H9210.9388N1—C131.487 (5)
OW2—H9220.9354N1—H110.8700
OW3—H9310.9277N1—H120.8700
OW3—H9320.9382N1—H130.8700
OW4—H9410.9307C13—C141.504 (5)
OW4—H9420.9214C13—H1310.9700
C1—O11.237 (4)C13—H1320.9700
C1—C21.476 (5)C14—N21.491 (5)
C1—C41.484 (5)C14—H1410.9700
C2—O21.249 (5)C14—H1420.9700
C2—C31.454 (5)N2—H210.9571
C3—O31.277 (4)N2—H220.9479
C3—C41.445 (5)N2—H230.8528
C4—O41.257 (5)N3—C151.479 (5)
C5—O51.265 (4)N3—H310.8700
C5—C61.453 (4)N3—H320.8700
C5—C81.456 (4)N3—H330.8700
C6—O61.264 (4)C15—C15iii1.512 (8)
C6—C71.476 (4)C15—H1510.9700
C7—O71.234 (4)C15—H1520.9700
C7—C81.482 (4)
O3—Y1—O12152.48 (8)C5—C6—C790.7 (3)
O3—Y1—O9i73.35 (8)C6—O6—Y1135.7 (2)
O12—Y1—O9i131.37 (8)O7—C7—C6134.9 (3)
O3—Y1—O6137.19 (8)O7—C7—C8136.6 (3)
O12—Y1—O668.55 (8)C6—C7—C888.4 (2)
O9i—Y1—O677.00 (8)O8—C8—C5133.6 (3)
O3—Y1—OW375.14 (9)O8—C8—C7136.0 (3)
O12—Y1—OW381.46 (10)C5—C8—C790.3 (2)
O9i—Y1—OW3116.50 (12)O9—C9—C12132.6 (3)
O6—Y1—OW3147.03 (9)O9—C9—C10137.1 (3)
O3—Y1—OW287.89 (8)C12—C9—C1090.2 (2)
O12—Y1—OW273.57 (8)C9—O9—Y1ii139.9 (2)
O9i—Y1—OW2150.02 (8)O10—C10—C9135.0 (3)
O6—Y1—OW2103.86 (9)O10—C10—C11135.7 (3)
OW3—Y1—OW279.37 (13)C9—C10—C1189.2 (2)
O3—Y1—OW174.04 (8)O11—C11—C12133.8 (3)
O12—Y1—OW1116.61 (9)O11—C11—C10137.0 (3)
O9i—Y1—OW181.66 (8)C12—C11—C1089.2 (2)
O6—Y1—OW171.68 (8)O12—C12—C9132.7 (3)
OW3—Y1—OW1137.23 (10)O12—C12—C11135.9 (3)
OW2—Y1—OW170.61 (9)C9—C12—C1191.4 (2)
O3—Y1—OW4114.74 (9)C12—O12—Y1145.1 (2)
O12—Y1—OW471.35 (9)C13—N1—H11109.5
O9i—Y1—OW471.44 (8)C13—N1—H12109.5
O6—Y1—OW483.21 (9)H11—N1—H12109.5
OW3—Y1—OW474.20 (11)C13—N1—H13109.5
OW2—Y1—OW4138.51 (9)H11—N1—H13109.5
OW1—Y1—OW4146.71 (8)H12—N1—H13109.5
Y1—OW1—H911122.4N1—C13—C14113.6 (3)
Y1—OW1—H912110.8N1—C13—H131108.8
H911—OW1—H912103.1C14—C13—H131108.8
Y1—OW2—H921138.7N1—C13—H132108.8
Y1—OW2—H922116.5C14—C13—H132108.8
H921—OW2—H92298.3H131—C13—H132107.7
Y1—OW3—H931142.9N2—C14—C13112.5 (3)
Y1—OW3—H932117.9N2—C14—H141109.1
H931—OW3—H93292.4C13—C14—H141109.1
Y1—OW4—H941122.0N2—C14—H142109.1
Y1—OW4—H942120.4C13—C14—H142109.1
H941—OW4—H942105.7H141—C14—H142107.8
O1—C1—C2133.9 (4)C14—N2—H21106.7
O1—C1—C4136.9 (4)C14—N2—H22110.2
C2—C1—C489.2 (3)H21—N2—H22113.9
O2—C2—C3134.3 (4)C14—N2—H23114.2
O2—C2—C1136.1 (3)H21—N2—H23101.0
C3—C2—C189.6 (3)H22—N2—H23110.5
O3—C3—C4133.1 (3)C15—N3—H31109.5
O3—C3—C2135.3 (3)C15—N3—H32109.5
C4—C3—C291.6 (3)H31—N3—H32109.5
C3—O3—Y1142.0 (2)C15—N3—H33109.5
O4—C4—C3133.9 (3)H31—N3—H33109.5
O4—C4—C1136.4 (3)H32—N3—H33109.5
C3—C4—C189.6 (3)N3—C15—C15iii110.7 (4)
O5—C5—C6135.6 (3)N3—C15—H151109.5
O5—C5—C8134.0 (3)C15iii—C15—H151109.5
C6—C5—C890.4 (2)N3—C15—H152109.5
O6—C6—C5136.6 (3)C15iii—C15—H152109.5
O6—C6—C7132.6 (3)H151—C15—H152108.1
D—H···AD—HH···AD···AD—H···A
N1—H12···O3iv0.872.213.027 (4)157
N1—H12···O9v0.872.362.929 (4)123
N1—H11···O4iv0.872.362.995 (4)131
N1—H11···O7v0.872.282.987 (4)138
N1—H13···O6v0.872.362.970 (4)127
N1—H13···O12v0.872.263.032 (4)148
N2—H23···O20.851.872.707 (4)167
N2—H21···O4iv0.961.922.832 (4)159
N2—H21···O7v0.962.462.952 (4)112
N2—H22···O5vi0.952.012.929 (4)163
N3—H31···O40.872.222.843 (4)129
N3—H32···O8vii0.872.182.788 (4)127
N3—H33···OW1viii0.872.402.997 (4)126
OW1—H911···O11viii0.941.742.676 (3)175
OW1—H912···O50.931.782.687 (3)166
OW2—H922···O110.941.952.885 (4)173
OW2—H921···O10viii0.941.792.726 (3)179
OW3—H931···O8ii0.931.942.857 (4)172
OW3—H932···O1iv0.942.042.954 (5)163
OW4—H942···O5ii0.921.862.779 (3)172
OW4—H941···O10i0.931.862.761 (4)163
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
N1—H12⋯O3i0.872.213.027 (4)157
N1—H12⋯O9ii0.872.362.929 (4)123
N1—H11⋯O4i0.872.362.995 (4)131
N1—H11⋯O7ii0.872.282.987 (4)138
N1—H13⋯O6ii0.872.362.970 (4)127
N1—H13⋯O12ii0.872.263.032 (4)148
N2—H23⋯O20.851.872.707 (4)167
N2—H21⋯O4i0.961.922.832 (4)159
N2—H21⋯O7ii0.962.462.952 (4)112
N2—H22⋯O5iii0.952.012.929 (4)163
N3—H31⋯O40.872.222.843 (4)129
N3—H32⋯O8iv0.872.182.788 (4)127
N3—H33⋯OW1v0.872.402.997 (4)126
OW1—H911⋯O11v0.941.742.676 (3)175
OW1—H912⋯O50.931.782.687 (3)166
OW2—H922⋯O110.941.952.885 (4)173
OW2—H921⋯O10v0.941.792.726 (3)179
OW3—H931⋯O8vi0.931.942.857 (4)172
OW3—H932⋯O1i0.942.042.954 (5)163
OW4—H942⋯O5vi0.921.862.779 (3)172
OW4—H941⋯O10vii0.931.862.761 (4)163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis, crystal structure from single-crystal and powder X-ray diffraction data, and thermal behavior of mixed potassium lanthanide squarates: thermal transformations of layered [Ln(H2O)6]K(H2C4O4)(C4O4)2 into pillared LnK(C4O4)2 (Ln = Y, La, Gd, Er).

Authors:  Nathalie Mahé; Thierry Bataille
Journal:  Inorg Chem       Date:  2004-12-27       Impact factor: 5.165

3.  A second monoclinic polymorph of ethyl-enediammonium bis-(hydrogen squarate) monohydrate.

Authors:  Louiza Zenkhri; Thierry Bataille; Nathalie Audebrand
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-13
  3 in total

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