Download citation
Download citation
link to html
Copper(II) bis­(4,4,4-tri­fluoro-1-phenyl­butane-1,3-dionate) complexes with pyri­din-2-one (pyon), 3-hy­droxy­pyridine (hpy) and 3-hy­droxy­pyridin-2-one (hpyon) were prepared and the solid-state structures of (pyridin-2-one-κO)bis­(4,4,4-tri­fluoro-3-oxo-1-phenyl­butan-1-olato-κ2O,O′)copper(II), [Cu(C10H6F3O2)2(C5H5NO)] or [Cu(tfpb-κ2O,O′)2(pyon-κO)], (I), bis­(pyridin-3-ol-κO)bis­(4,4,4-tri­fluoro-3-oxo-1-phenyl­butan-1-olato-κ2O,O′)copper(II), [Cu(C10H6F3O2)2(C5H5NO)2] or [Cu(tfpb-κ2O,O′)2(hpy-κO)2], (II), and bis­(3-hy­droxy­pyridin-2-one-κO)bis­(4,4,4-tri­fluoro-3-oxo-1-phenyl­butan-1-olato-κ2O,O′)copper(II), [Cu(C10H6F3O2)2(C5H5NO2)2] or [Cu(tfpb-κ2O,O′)2(hpyon-κO)2], (III), were determined by single-crystal X-ray analysis. The coordination of the metal centre is square pyramidal and displays a rare example of a mutual cis arrangement of the β-diketonate ligands in (I) and a trans-octa­hedral arrangement in (II) and (III). Complex (II) presents the first crystallographic evidence of κO-monodentate hpy ligation to the transition metal enabling the pyridine N atom to participate in a two-dimensional hydrogen-bonded network through O—H...N inter­actions, forming a graph-set motif R22(7) through a C—H...O inter­action. Complex (III) presents the first crystallographic evidence of monodentate coordination of the neutral hpyon ligand to a metal centre and a two-dimensional hydrogen-bonded network is formed through N—H...O inter­actions facilitated by C—H...O inter­actions, forming the graph-set motifs R22(8) and R22(7).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617014875/ku3208sup1.cif
Contains datablocks I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014875/ku3208Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014875/ku3208IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014875/ku3208IIIsup4.hkl
Contains datablock III

CCDC references: 1579882; 1579881; 1579880

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013) for (I), (II); KappaCCD Reference Manual (Nonius, 1998) for (III). Cell refinement: CrysAlis PRO (Agilent, 2013) for (I), (II); DENZO-SMN (Otwinowski & Minor, 1997) for (III). Data reduction: CrysAlis PRO (Agilent, 2013) for (I), (II); DENZO-SMN (Otwinowski & Minor, 1997) for (III). For all structures, program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

(Pyridin-2-one-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ2O,O')copper(II) (I) top
Crystal data top
[Cu(C10H6F3O2)2(C5H5NO)]Z = 2
Mr = 588.93F(000) = 594
Triclinic, P1Dx = 1.563 Mg m3
a = 10.5928 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7082 (5) ÅCell parameters from 3680 reflections
c = 12.4943 (6) Åθ = 3.2–30.3°
α = 69.019 (4)°µ = 0.95 mm1
β = 71.705 (4)°T = 293 K
γ = 88.110 (3)°Prism, green
V = 1251.32 (11) Å30.30 × 0.10 × 0.07 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
5718 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3312 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.046
Detector resolution: 10.4933 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 1013
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1313
Tmin = 0.624, Tmax = 1.000l = 1516
11601 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0468P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
5718 reflectionsΔρmax = 0.40 e Å3
343 parametersΔρmin = 0.35 e Å3
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
Cu10.58853 (3)0.39870 (4)0.28948 (4)0.05204 (15)
F10.7402 (3)0.0908 (3)0.1205 (3)0.1212 (10)
F20.8231 (3)0.0208 (3)0.2596 (3)0.1413 (12)
F30.9421 (3)0.1394 (3)0.0819 (3)0.1255 (10)
F40.1793 (2)0.2241 (2)0.3400 (3)0.1066 (8)
F50.1644 (2)0.1643 (2)0.5245 (2)0.1124 (9)
F60.06941 (19)0.3330 (2)0.4445 (2)0.0961 (8)
N10.5596 (2)0.6869 (2)0.0643 (2)0.0499 (6)
H10.52350.63000.08260.060*
O10.6654 (2)0.2525 (2)0.2415 (2)0.0591 (6)
O20.76087 (19)0.4821 (2)0.2586 (2)0.0583 (6)
O30.41156 (19)0.30902 (19)0.34400 (19)0.0541 (5)
O40.52249 (19)0.5380 (2)0.35046 (19)0.0545 (5)
O50.5752 (2)0.5152 (2)0.0993 (2)0.0584 (6)
C10.8260 (4)0.1249 (4)0.1643 (4)0.0781 (11)
C20.7895 (3)0.2491 (3)0.1970 (3)0.0560 (8)
C30.8926 (3)0.3370 (3)0.1784 (3)0.0613 (9)
H30.97920.32080.14140.074*
C40.8749 (3)0.4497 (3)0.2118 (3)0.0525 (8)
C50.9900 (3)0.5387 (3)0.1952 (3)0.0533 (8)
C60.9665 (4)0.6400 (4)0.2407 (3)0.0709 (10)
H60.87930.65220.27990.085*
C71.0708 (4)0.7240 (4)0.2290 (4)0.0854 (12)
H71.05370.79270.25920.102*
C81.1995 (4)0.7048 (4)0.1723 (4)0.0861 (12)
H81.27020.76030.16440.103*
C91.2235 (4)0.6046 (5)0.1279 (4)0.0941 (13)
H91.31110.59210.08980.113*
C101.1208 (3)0.5213 (4)0.1382 (3)0.0724 (10)
H101.13900.45330.10700.087*
C110.1793 (3)0.2699 (4)0.4254 (4)0.0683 (10)
C120.3065 (3)0.3571 (3)0.3913 (3)0.0502 (8)
C130.2941 (3)0.4714 (3)0.4176 (3)0.0570 (8)
H130.20870.49130.45340.068*
C140.4030 (3)0.5607 (3)0.3934 (3)0.0462 (7)
C150.3829 (3)0.6878 (3)0.4162 (3)0.0495 (7)
C160.4935 (3)0.7720 (3)0.3902 (3)0.0637 (9)
H160.57850.74670.36110.076*
C170.4796 (4)0.8934 (3)0.4069 (4)0.0750 (11)
H170.55500.94860.38950.090*
C180.3563 (4)0.9318 (4)0.4486 (3)0.0749 (11)
H180.34701.01400.45860.090*
C190.2452 (4)0.8493 (4)0.4762 (4)0.0778 (11)
H190.16070.87500.50640.093*
C200.2580 (3)0.7281 (3)0.4595 (3)0.0660 (10)
H200.18210.67330.47740.079*
C210.5976 (3)0.6387 (3)0.0357 (3)0.0502 (8)
C220.6599 (4)0.7356 (4)0.0596 (3)0.0750 (11)
H220.69000.70900.12620.090*
C230.6764 (5)0.8672 (4)0.0134 (4)0.0991 (15)
H230.71820.92970.00330.119*
C240.6310 (5)0.9095 (4)0.1134 (4)0.0935 (14)
H240.64010.99990.16230.112*
C250.5740 (4)0.8173 (3)0.1376 (3)0.0690 (10)
H250.54450.84300.20450.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0426 (2)0.0611 (3)0.0610 (3)0.00950 (17)0.01601 (19)0.0334 (2)
F10.131 (2)0.120 (2)0.165 (3)0.0308 (16)0.056 (2)0.107 (2)
F20.229 (3)0.0756 (16)0.110 (2)0.0676 (19)0.050 (2)0.0320 (16)
F30.0998 (19)0.119 (2)0.153 (2)0.0148 (15)0.0152 (17)0.0934 (19)
F40.0747 (16)0.122 (2)0.144 (2)0.0157 (13)0.0264 (15)0.0798 (19)
F50.0900 (17)0.0710 (15)0.122 (2)0.0129 (12)0.0116 (15)0.0091 (15)
F60.0464 (12)0.0781 (14)0.160 (2)0.0045 (10)0.0219 (13)0.0490 (15)
N10.0537 (16)0.0483 (15)0.0504 (17)0.0024 (11)0.0140 (13)0.0231 (13)
O10.0504 (14)0.0620 (13)0.0724 (16)0.0105 (10)0.0180 (12)0.0353 (12)
O20.0413 (13)0.0721 (14)0.0750 (16)0.0135 (10)0.0200 (11)0.0424 (13)
O30.0460 (13)0.0568 (13)0.0636 (15)0.0059 (10)0.0129 (11)0.0310 (11)
O40.0430 (13)0.0653 (13)0.0643 (15)0.0055 (10)0.0128 (11)0.0382 (12)
O50.0709 (15)0.0520 (13)0.0585 (15)0.0022 (10)0.0279 (12)0.0208 (11)
C10.084 (3)0.071 (3)0.083 (3)0.024 (2)0.017 (3)0.042 (2)
C20.058 (2)0.061 (2)0.051 (2)0.0155 (17)0.0154 (17)0.0255 (17)
C30.050 (2)0.076 (2)0.060 (2)0.0141 (17)0.0098 (17)0.0344 (19)
C40.0450 (19)0.066 (2)0.049 (2)0.0126 (15)0.0172 (16)0.0232 (17)
C50.046 (2)0.068 (2)0.0418 (19)0.0055 (15)0.0144 (16)0.0152 (16)
C60.051 (2)0.088 (3)0.078 (3)0.0015 (18)0.0122 (19)0.043 (2)
C70.075 (3)0.092 (3)0.099 (3)0.005 (2)0.025 (3)0.048 (3)
C80.059 (3)0.101 (3)0.091 (3)0.019 (2)0.019 (2)0.029 (3)
C90.050 (3)0.116 (4)0.109 (4)0.001 (2)0.008 (2)0.047 (3)
C100.045 (2)0.090 (3)0.080 (3)0.0023 (19)0.0092 (19)0.038 (2)
C110.054 (2)0.055 (2)0.086 (3)0.0018 (17)0.013 (2)0.023 (2)
C120.0449 (19)0.0501 (18)0.051 (2)0.0030 (14)0.0146 (16)0.0140 (16)
C130.0424 (19)0.0543 (19)0.070 (2)0.0063 (14)0.0087 (16)0.0257 (17)
C140.0454 (19)0.0537 (18)0.0390 (18)0.0097 (14)0.0129 (14)0.0175 (15)
C150.054 (2)0.0523 (18)0.0429 (18)0.0076 (15)0.0147 (15)0.0196 (15)
C160.057 (2)0.065 (2)0.075 (3)0.0066 (17)0.0193 (19)0.0336 (19)
C170.081 (3)0.065 (2)0.088 (3)0.0017 (19)0.030 (2)0.035 (2)
C180.100 (3)0.061 (2)0.081 (3)0.022 (2)0.039 (2)0.038 (2)
C190.079 (3)0.070 (2)0.090 (3)0.027 (2)0.020 (2)0.043 (2)
C200.054 (2)0.066 (2)0.085 (3)0.0127 (16)0.0174 (19)0.040 (2)
C210.0498 (19)0.0538 (19)0.049 (2)0.0002 (15)0.0106 (16)0.0256 (17)
C220.100 (3)0.068 (2)0.069 (3)0.009 (2)0.042 (2)0.026 (2)
C230.151 (4)0.068 (3)0.095 (3)0.023 (3)0.060 (3)0.030 (3)
C240.153 (4)0.051 (2)0.083 (3)0.012 (2)0.054 (3)0.016 (2)
C250.092 (3)0.057 (2)0.060 (2)0.0014 (18)0.030 (2)0.0181 (19)
Geometric parameters (Å, º) top
Cu1—O11.938 (2)C8—C91.358 (5)
Cu1—O21.923 (2)C8—H80.9300
Cu1—O31.936 (2)C9—C101.375 (5)
Cu1—O41.9251 (19)C9—H90.9300
Cu1—O52.302 (2)C10—H100.9300
F1—C11.318 (4)C11—C121.519 (4)
F2—C11.300 (4)C12—C131.369 (4)
F3—C11.304 (4)C13—C141.409 (4)
F4—C111.324 (4)C13—H130.9300
F5—C111.313 (4)C14—C151.483 (4)
F6—C111.326 (4)C15—C201.382 (4)
N1—C251.350 (4)C15—C161.383 (4)
N1—C211.352 (4)C16—C171.384 (4)
N1—H10.8600C16—H160.9300
O1—C21.262 (3)C17—C181.356 (5)
O2—C41.263 (3)C17—H170.9300
O3—C121.273 (3)C18—C191.371 (5)
O4—C141.263 (3)C18—H180.9300
O5—C211.260 (3)C19—C201.382 (4)
C1—C21.530 (4)C19—H190.9300
C2—C31.373 (4)C20—H200.9300
C3—C41.401 (4)C21—C221.411 (4)
C3—H30.9300C22—C231.358 (5)
C4—C51.488 (4)C22—H220.9300
C5—C61.377 (4)C23—C241.399 (5)
C5—C101.386 (4)C23—H230.9300
C6—C71.386 (5)C24—C251.341 (5)
C6—H60.9300C24—H240.9300
C7—C81.372 (5)C25—H250.9300
C7—H70.9300
O1—Cu1—O591.53 (8)C5—C10—H10120.1
O2—Cu1—O192.59 (9)F5—C11—F4106.6 (3)
O2—Cu1—O3172.09 (9)F5—C11—F6106.9 (3)
O2—Cu1—O483.96 (8)F4—C11—F6105.8 (3)
O2—Cu1—O595.61 (8)F5—C11—C12111.2 (3)
O3—Cu1—O190.14 (8)F4—C11—C12112.2 (3)
O4—Cu1—O392.59 (8)F6—C11—C12113.8 (3)
O3—Cu1—O591.73 (8)O3—C12—C13129.3 (3)
O4—Cu1—O1173.55 (9)O3—C12—C11113.3 (3)
O4—Cu1—O594.23 (8)C13—C12—C11117.4 (3)
C25—N1—C21125.1 (3)C12—C13—C14123.8 (3)
C25—N1—H1117.5C12—C13—H13118.1
C21—N1—H1117.5C14—C13—H13118.1
C2—O1—Cu1122.8 (2)O4—C14—C13122.2 (3)
C4—O2—Cu1128.5 (2)O4—C14—C15116.4 (3)
C12—O3—Cu1122.78 (19)C13—C14—C15121.4 (3)
C14—O4—Cu1128.72 (19)C20—C15—C16118.1 (3)
C21—O5—Cu1130.60 (19)C20—C15—C14122.9 (3)
F2—C1—F3108.4 (3)C16—C15—C14118.9 (3)
F2—C1—F1105.4 (4)C15—C16—C17120.9 (3)
F3—C1—F1105.0 (4)C15—C16—H16119.5
F2—C1—C2111.1 (3)C17—C16—H16119.5
F3—C1—C2114.4 (3)C18—C17—C16120.1 (4)
F1—C1—C2112.0 (3)C18—C17—H17119.9
O1—C2—C3129.4 (3)C16—C17—H17119.9
O1—C2—C1113.2 (3)C17—C18—C19119.9 (3)
C3—C2—C1117.4 (3)C17—C18—H18120.0
C2—C3—C4123.8 (3)C19—C18—H18120.0
C2—C3—H3118.1C18—C19—C20120.4 (3)
C4—C3—H3118.1C18—C19—H19119.8
O2—C4—C3122.6 (3)C20—C19—H19119.8
O2—C4—C5115.5 (3)C15—C20—C19120.5 (3)
C3—C4—C5122.0 (3)C15—C20—H20119.8
C6—C5—C10118.6 (3)C19—C20—H20119.8
C6—C5—C4119.1 (3)O5—C21—N1119.3 (3)
C10—C5—C4122.3 (3)O5—C21—C22125.5 (3)
C5—C6—C7121.1 (3)N1—C21—C22115.2 (3)
C5—C6—H6119.5C23—C22—C21120.8 (3)
C7—C6—H6119.5C23—C22—H22119.6
C8—C7—C6119.4 (4)C21—C22—H22119.6
C8—C7—H7120.3C22—C23—C24120.5 (4)
C6—C7—H7120.3C22—C23—H23119.7
C9—C8—C7119.9 (4)C24—C23—H23119.7
C9—C8—H8120.0C25—C24—C23118.7 (4)
C7—C8—H8120.0C25—C24—H24120.6
C8—C9—C10121.2 (4)C23—C24—H24120.6
C8—C9—H9119.4C24—C25—N1119.7 (3)
C10—C9—H9119.4C24—C25—H25120.2
C9—C10—C5119.9 (4)N1—C25—H25120.2
C9—C10—H10120.1
Cu1—O1—C2—C33.2 (5)F5—C11—C12—C13102.3 (4)
Cu1—O1—C2—C1179.1 (2)F4—C11—C12—C13138.4 (3)
F2—C1—C2—O180.2 (4)F6—C11—C12—C1318.4 (5)
F3—C1—C2—O1156.6 (3)O3—C12—C13—C140.8 (6)
F1—C1—C2—O137.4 (5)C11—C12—C13—C14178.8 (3)
F2—C1—C2—C397.9 (4)Cu1—O4—C14—C138.4 (4)
F3—C1—C2—C325.3 (5)Cu1—O4—C14—C15171.08 (19)
F1—C1—C2—C3144.6 (4)C12—C13—C14—O43.6 (5)
O1—C2—C3—C42.3 (6)C12—C13—C14—C15175.8 (3)
C1—C2—C3—C4175.4 (3)O4—C14—C15—C20178.0 (3)
Cu1—O2—C4—C33.0 (5)C13—C14—C15—C201.5 (5)
Cu1—O2—C4—C5177.45 (19)O4—C14—C15—C160.2 (4)
C2—C3—C4—O22.5 (5)C13—C14—C15—C16179.7 (3)
C2—C3—C4—C5177.0 (3)C20—C15—C16—C170.1 (5)
O2—C4—C5—C65.9 (4)C14—C15—C16—C17178.2 (3)
C3—C4—C5—C6173.6 (3)C15—C16—C17—C180.4 (6)
O2—C4—C5—C10175.9 (3)C16—C17—C18—C191.1 (6)
C3—C4—C5—C104.6 (5)C17—C18—C19—C201.3 (6)
C10—C5—C6—C70.7 (5)C16—C15—C20—C190.1 (5)
C4—C5—C6—C7179.0 (3)C14—C15—C20—C19178.4 (3)
C5—C6—C7—C80.8 (6)C18—C19—C20—C150.8 (6)
C6—C7—C8—C90.3 (7)Cu1—O5—C21—N1168.01 (18)
C7—C8—C9—C100.2 (7)Cu1—O5—C21—C2211.5 (5)
C8—C9—C10—C50.2 (6)C25—N1—C21—O5177.8 (3)
C6—C5—C10—C90.2 (5)C25—N1—C21—C221.8 (4)
C4—C5—C10—C9178.4 (3)O5—C21—C22—C23178.3 (4)
Cu1—O3—C12—C132.7 (5)N1—C21—C22—C231.2 (5)
Cu1—O3—C12—C11179.2 (2)C21—C22—C23—C240.5 (7)
F5—C11—C12—O376.0 (4)C22—C23—C24—C251.7 (7)
F4—C11—C12—O343.2 (4)C23—C24—C25—N11.1 (6)
F6—C11—C12—O3163.3 (3)C21—N1—C25—C240.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.862.012.861 (3)172
C20—H20···F6ii0.932.533.297 (4)140
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
Bis(pyridin-3-ol-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ2O,O')copper(II) (II) top
Crystal data top
[Cu(C10H6F3O2)2(C5H5NO)2]F(000) = 694
Mr = 684.03Dx = 1.517 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 10.0085 (3) ÅCell parameters from 3917 reflections
b = 14.1540 (5) Åθ = 3.1–73.9°
c = 11.2503 (3) ŵ = 1.78 mm1
β = 110.022 (4)°T = 293 K
V = 1497.40 (9) Å3Prism, green
Z = 20.20 × 0.15 × 0.10 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
3056 independent reflections
Radiation source: SuperNova (Cu) X-ray Source2620 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.021
Detector resolution: 10.4933 pixels mm-1θmax = 74.7°, θmin = 4.7°
ω scansh = 1211
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1716
Tmin = 0.598, Tmax = 1.000l = 1412
9185 measured reflections
Refinement top
Refinement on F279 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0947P)2 + 0.4325P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3056 reflectionsΔρmax = 0.36 e Å3
236 parametersΔρmin = 0.41 e Å3
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*/UeqOcc. (<1)
Cu10.00000.00000.00000.04884 (19)
O10.1295 (2)0.00417 (12)0.17135 (17)0.0593 (4)
O20.14105 (17)0.04725 (12)0.06650 (14)0.0542 (4)
O30.0495 (2)0.17394 (13)0.04118 (16)0.0709 (5)
H3A0.062 (4)0.190 (3)0.107 (2)0.106*
N10.0919 (3)0.30935 (16)0.23815 (18)0.0648 (5)
F1A0.3127 (19)0.0286 (12)0.3949 (10)0.184 (8)0.59 (4)
F2A0.4555 (18)0.074 (2)0.3789 (15)0.175 (7)0.59 (4)
F3A0.257 (3)0.116 (2)0.3860 (13)0.187 (7)0.59 (4)
F1B0.348 (2)0.0289 (9)0.3999 (13)0.120 (5)0.41 (4)
F2B0.425 (3)0.1074 (16)0.383 (2)0.145 (8)0.41 (4)
F3B0.2202 (19)0.0888 (18)0.4060 (14)0.135 (5)0.41 (4)
C10.3169 (4)0.0539 (4)0.3451 (4)0.1034 (14)
C20.2469 (3)0.0467 (2)0.2023 (2)0.0650 (6)
C30.3157 (3)0.0851 (2)0.1273 (3)0.0726 (7)
H30.40230.11530.16590.087*
C40.2613 (2)0.08066 (17)0.0050 (2)0.0549 (5)
C50.3461 (3)0.1165 (2)0.0825 (3)0.0704 (7)
C60.2776 (4)0.1348 (2)0.2099 (3)0.0820 (8)
H60.17950.12740.24480.098*
C70.3538 (5)0.1643 (3)0.2868 (4)0.1048 (10)
H70.30710.17600.37240.126*
C80.4972 (5)0.1757 (4)0.2346 (5)0.1203 (12)
H80.54860.19640.28460.144*
C90.5661 (5)0.1569 (4)0.1096 (6)0.1233 (13)
H90.66450.16310.07680.148*
C100.4925 (4)0.1284 (3)0.0283 (5)0.1014 (10)
H100.54000.11800.05750.122*
C110.0666 (3)0.23974 (17)0.1548 (2)0.0579 (5)
H110.04030.18120.17710.069*
C120.0775 (3)0.24977 (16)0.0357 (2)0.0544 (5)
C130.1180 (4)0.3357 (2)0.0039 (3)0.0785 (8)
H130.12600.34540.07520.094*
C140.1466 (5)0.4077 (2)0.0917 (3)0.0984 (10)
H140.17580.46650.07290.118*
C150.1317 (5)0.3921 (2)0.2072 (3)0.0907 (9)
H150.15030.44130.26540.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0547 (3)0.0562 (3)0.0366 (3)0.00421 (18)0.01693 (19)0.00072 (16)
O10.0645 (10)0.0693 (11)0.0413 (8)0.0057 (8)0.0145 (7)0.0052 (6)
O20.0619 (9)0.0586 (9)0.0461 (8)0.0057 (7)0.0236 (7)0.0035 (7)
O30.1194 (15)0.0592 (9)0.0471 (8)0.0208 (10)0.0455 (9)0.0097 (7)
N10.1027 (15)0.0562 (11)0.0481 (9)0.0071 (10)0.0421 (10)0.0053 (8)
F1A0.122 (6)0.307 (18)0.082 (4)0.083 (8)0.020 (4)0.105 (7)
F2A0.098 (5)0.305 (19)0.074 (5)0.079 (9)0.032 (3)0.059 (9)
F3A0.209 (12)0.286 (16)0.054 (4)0.016 (11)0.030 (5)0.059 (7)
F1B0.118 (8)0.118 (8)0.077 (5)0.001 (6)0.027 (5)0.036 (5)
F2B0.173 (19)0.152 (11)0.067 (5)0.084 (10)0.013 (8)0.001 (6)
F3B0.131 (7)0.220 (12)0.048 (4)0.014 (7)0.023 (4)0.003 (6)
C10.094 (2)0.141 (4)0.0528 (18)0.032 (3)0.0031 (17)0.014 (2)
C20.0656 (14)0.0714 (16)0.0482 (12)0.0046 (12)0.0066 (10)0.0077 (11)
C30.0641 (14)0.0820 (18)0.0620 (14)0.0186 (13)0.0092 (12)0.0082 (13)
C40.0569 (12)0.0509 (12)0.0596 (12)0.0013 (9)0.0235 (10)0.0024 (10)
C50.0742 (14)0.0598 (13)0.0906 (17)0.0045 (11)0.0454 (13)0.0088 (12)
C60.1052 (19)0.0756 (17)0.0837 (17)0.0127 (15)0.0563 (15)0.0017 (14)
C70.139 (2)0.094 (2)0.110 (2)0.014 (2)0.080 (2)0.0074 (18)
C80.129 (3)0.113 (3)0.155 (3)0.014 (2)0.094 (2)0.017 (2)
C90.093 (2)0.123 (3)0.175 (3)0.012 (2)0.072 (2)0.022 (3)
C100.0732 (16)0.101 (2)0.139 (3)0.0080 (15)0.0488 (18)0.025 (2)
C110.0856 (14)0.0530 (11)0.0444 (11)0.0060 (11)0.0343 (10)0.0022 (9)
C120.0783 (13)0.0510 (11)0.0434 (10)0.0039 (10)0.0332 (9)0.0039 (8)
C130.137 (2)0.0607 (14)0.0575 (13)0.0161 (15)0.0589 (14)0.0044 (11)
C140.182 (3)0.0616 (15)0.0744 (16)0.0310 (18)0.0732 (18)0.0105 (13)
C150.164 (3)0.0604 (14)0.0671 (15)0.0230 (16)0.0643 (16)0.0167 (12)
Geometric parameters (Å, º) top
Cu1—O11.9204 (18)C4—C51.499 (3)
Cu1—O1i1.9204 (18)C5—C61.385 (5)
Cu1—O21.9296 (15)C5—C101.391 (4)
Cu1—O2i1.9296 (15)C6—C71.399 (5)
Cu1—O32.5841 (18)C6—H60.9300
O1—C21.259 (3)C7—C81.362 (7)
O2—C41.257 (3)C7—H70.9300
O3—C121.346 (3)C8—C91.364 (7)
O3—H3A0.821 (10)C8—H80.9300
N1—C151.322 (4)C9—C101.415 (6)
N1—C111.323 (3)C9—H90.9300
F1A—C11.302 (14)C10—H100.9300
F2A—C11.339 (16)C11—C121.389 (3)
F3A—C11.243 (18)C11—H110.9300
F1B—C11.312 (12)C12—C131.367 (4)
F2B—C11.27 (2)C13—C141.380 (4)
F3B—C11.45 (2)C13—H130.9300
C1—C21.520 (4)C14—C151.376 (4)
C2—C31.371 (4)C14—H140.9300
C3—C41.400 (4)C15—H150.9300
C3—H30.9300
O1—Cu1—O1i180.0O2—C4—C5115.7 (2)
O1—Cu1—O292.68 (7)C3—C4—C5120.7 (2)
O1i—Cu1—O287.32 (7)C6—C5—C10120.4 (3)
O1—Cu1—O2i87.32 (7)C6—C5—C4119.1 (3)
O1i—Cu1—O2i92.68 (7)C10—C5—C4120.5 (3)
O2—Cu1—O2i180.0C5—C6—C7120.9 (4)
O1—Cu1—O384.01 (7)C5—C6—H6119.5
O1i—Cu1—O395.99 (7)C7—C6—H6119.5
O2—Cu1—O387.12 (7)C8—C7—C6119.1 (4)
O2i—Cu1—O392.88 (7)C8—C7—H7120.4
C2—O1—Cu1122.51 (16)C6—C7—H7120.4
C4—O2—Cu1127.33 (15)C7—C8—C9120.5 (4)
C12—O3—Cu1130.93 (13)C7—C8—H8119.8
C12—O3—H3A107 (3)C9—C8—H8119.8
Cu1—O3—H3A121 (3)C8—C9—C10122.1 (4)
C15—N1—C11118.4 (2)C8—C9—H9118.9
F3A—C1—F1A112.7 (13)C10—C9—H9118.9
F2B—C1—F1B109.8 (13)C5—C10—C9117.0 (4)
F3A—C1—F2A109.1 (11)C5—C10—H10121.5
F1A—C1—F2A104.8 (10)C9—C10—H10121.5
F2B—C1—F3B105.5 (15)N1—C11—C12123.3 (2)
F1B—C1—F3B99.8 (10)N1—C11—H11118.4
F3A—C1—C2109.4 (7)C12—C11—H11118.4
F2B—C1—C2115.3 (12)O3—C12—C13123.8 (2)
F1A—C1—C2108.9 (7)O3—C12—C11118.1 (2)
F1B—C1—C2112.7 (7)C13—C12—C11118.1 (2)
F2A—C1—C2111.9 (9)C12—C13—C14118.5 (2)
F3B—C1—C2112.4 (7)C12—C13—H13120.7
O1—C2—C3129.6 (2)C14—C13—H13120.7
O1—C2—C1111.9 (3)C15—C14—C13119.7 (3)
C3—C2—C1118.5 (3)C15—C14—H14120.2
C2—C3—C4122.8 (2)C13—C14—H14120.2
C2—C3—H3118.6N1—C15—C14122.0 (3)
C4—C3—H3118.6N1—C15—H15119.0
O2—C4—C3123.6 (2)C14—C15—H15119.0
Cu1—O1—C2—C310.0 (5)C3—C4—C5—C6162.8 (3)
Cu1—O1—C2—C1170.1 (3)O2—C4—C5—C10160.7 (3)
F3A—C1—C2—O176.3 (18)C3—C4—C5—C1019.2 (5)
F2B—C1—C2—O1170.2 (17)C10—C5—C6—C70.8 (5)
F1A—C1—C2—O147.3 (10)C4—C5—C6—C7177.1 (3)
F1B—C1—C2—O162.6 (12)C5—C6—C7—C80.5 (6)
F2A—C1—C2—O1162.7 (15)C6—C7—C8—C91.2 (8)
F3B—C1—C2—O149.2 (12)C7—C8—C9—C102.2 (8)
F3A—C1—C2—C3103.8 (18)C6—C5—C10—C91.7 (6)
F2B—C1—C2—C39.9 (17)C4—C5—C10—C9176.2 (4)
F1A—C1—C2—C3132.6 (10)C8—C9—C10—C52.4 (8)
F1B—C1—C2—C3117.3 (11)C15—N1—C11—C121.1 (5)
F2A—C1—C2—C317.3 (16)Cu1—O3—C12—C13172.0 (2)
F3B—C1—C2—C3130.8 (11)Cu1—O3—C12—C117.0 (4)
O1—C2—C3—C41.0 (6)N1—C11—C12—O3179.9 (3)
C1—C2—C3—C4178.9 (4)N1—C11—C12—C130.8 (4)
Cu1—O2—C4—C33.0 (4)O3—C12—C13—C14178.7 (3)
Cu1—O2—C4—C5177.12 (17)C11—C12—C13—C140.4 (5)
C2—C3—C4—O25.1 (5)C12—C13—C14—C151.1 (7)
C2—C3—C4—C5174.9 (3)C11—N1—C15—C140.4 (6)
O2—C4—C5—C617.2 (4)C13—C14—C15—N10.7 (7)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N1ii0.82 (1)1.87 (2)2.669 (2)165 (4)
C15—H15···O2iii0.932.443.339 (3)163
Symmetry codes: (ii) x, y1/2, z+1/2; (iii) x, y1/2, z1/2.
Bis(3-hydroxypyridin-2-one-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ2O,O')copper(II) (III) top
Crystal data top
[Cu(C10H6F3O2)2(C5H5NO2)2]Z = 1
Mr = 716.03F(000) = 363
Triclinic, P1Dx = 1.639 Mg m3
a = 7.5950 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6764 (4) ÅCell parameters from 3204 reflections
c = 10.7507 (4) Åθ = 1.0–27.5°
α = 108.710 (2)°µ = 0.85 mm1
β = 101.727 (2)°T = 293 K
γ = 93.650 (2)°Block, green
V = 725.61 (5) Å30.25 × 0.15 × 0.10 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
3300 independent reflections
Radiation source: fine-focus sealed tube2905 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 0.055 pixels mm-1θmax = 27.5°, θmin = 3.5°
ω scansh = 99
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 1212
Tmin = 0.860, Tmax = 1.000l = 1313
5704 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0388P)2 + 0.3054P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3300 reflectionsΔρmax = 0.30 e Å3
243 parametersΔρmin = 0.41 e Å3
Special details top

Experimental. 185 frames in 4 sets of ω scans. Rotation/frame = 2.0 °. Crystal-detector distance = 25.0 mm. Measuring time = 20 s/°.

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*/UeqOcc. (<1)
Cu10.50000.00000.00000.03159 (11)
F1A0.0866 (12)0.4652 (6)0.3582 (8)0.0752 (17)0.70 (3)
F2A0.2240 (12)0.3169 (12)0.4232 (7)0.081 (2)0.70 (3)
F3A0.0052 (11)0.2623 (14)0.3483 (10)0.082 (2)0.70 (3)
F1B0.044 (4)0.447 (3)0.3514 (16)0.099 (6)0.30 (3)
F2B0.240 (3)0.345 (2)0.4194 (19)0.080 (5)0.30 (3)
F3B0.027 (4)0.235 (4)0.359 (2)0.107 (8)0.30 (3)
O10.49487 (17)0.15660 (13)0.07642 (12)0.0332 (3)
O20.34867 (18)0.12645 (14)0.17153 (12)0.0349 (3)
O30.23113 (18)0.05953 (15)0.10040 (13)0.0369 (3)
O40.4467 (2)0.07809 (19)0.35085 (14)0.0486 (4)
H40.48060.09510.28890.073*
N10.0005 (2)0.07098 (18)0.13890 (16)0.0376 (4)
H10.06720.07500.06260.045*
C10.1407 (3)0.3234 (2)0.3307 (2)0.0412 (4)
C20.2618 (2)0.25088 (19)0.18802 (17)0.0323 (4)
C30.2636 (3)0.3231 (2)0.09762 (19)0.0391 (4)
H30.18230.40880.12260.047*
C40.3834 (2)0.27387 (18)0.03228 (17)0.0306 (4)
C50.3844 (3)0.36172 (19)0.12376 (19)0.0335 (4)
C60.4900 (3)0.3036 (2)0.2549 (2)0.0416 (4)
H60.55940.21150.28380.050*
C70.4934 (4)0.3812 (3)0.3432 (2)0.0543 (6)
H70.56470.34150.43100.065*
C80.3902 (4)0.5179 (3)0.3004 (3)0.0591 (6)
H80.39250.57050.35930.071*
C90.2853 (4)0.5760 (3)0.1720 (3)0.0614 (7)
H90.21600.66800.14410.074*
C100.2804 (4)0.4995 (2)0.0826 (2)0.0496 (5)
H100.20780.54000.00480.059*
C110.1710 (2)0.00097 (19)0.17594 (17)0.0309 (4)
C120.2756 (3)0.0047 (2)0.30454 (18)0.0355 (4)
C130.2041 (3)0.0627 (3)0.3800 (2)0.0455 (5)
H130.27400.06010.46270.055*
C140.0255 (3)0.1360 (3)0.3337 (2)0.0527 (6)
H140.02340.18300.38460.063*
C150.0745 (3)0.1373 (3)0.2139 (2)0.0485 (5)
H150.19390.18360.18280.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03573 (18)0.02923 (16)0.02486 (16)0.00841 (12)0.00491 (12)0.01239 (12)
F1A0.107 (4)0.036 (2)0.051 (2)0.018 (3)0.027 (2)0.0059 (15)
F2A0.082 (4)0.113 (4)0.027 (2)0.045 (3)0.001 (2)0.014 (2)
F3A0.052 (2)0.089 (5)0.068 (3)0.016 (2)0.0214 (19)0.001 (2)
F1B0.109 (9)0.116 (11)0.039 (5)0.098 (8)0.024 (5)0.028 (6)
F2B0.061 (6)0.117 (9)0.033 (6)0.022 (7)0.009 (4)0.013 (5)
F3B0.129 (15)0.082 (9)0.052 (6)0.041 (11)0.063 (8)0.008 (5)
O10.0356 (7)0.0311 (6)0.0289 (6)0.0064 (5)0.0037 (5)0.0137 (5)
O20.0380 (7)0.0346 (6)0.0273 (6)0.0093 (5)0.0025 (5)0.0130 (5)
O30.0363 (7)0.0423 (7)0.0332 (7)0.0001 (6)0.0009 (5)0.0202 (6)
O40.0398 (8)0.0713 (10)0.0288 (7)0.0107 (7)0.0038 (6)0.0199 (7)
N10.0310 (8)0.0487 (9)0.0329 (8)0.0016 (7)0.0009 (6)0.0198 (7)
C10.0431 (11)0.0397 (10)0.0317 (10)0.0091 (8)0.0022 (8)0.0093 (8)
C20.0319 (9)0.0329 (8)0.0251 (8)0.0059 (7)0.0002 (7)0.0067 (7)
C30.0426 (11)0.0348 (9)0.0331 (9)0.0135 (8)0.0012 (8)0.0122 (8)
C40.0330 (9)0.0289 (8)0.0297 (9)0.0000 (7)0.0064 (7)0.0112 (7)
C50.0383 (10)0.0305 (8)0.0357 (9)0.0043 (7)0.0119 (8)0.0147 (7)
C60.0500 (12)0.0419 (10)0.0353 (10)0.0008 (9)0.0073 (9)0.0190 (8)
C70.0705 (16)0.0587 (13)0.0404 (12)0.0072 (12)0.0104 (11)0.0279 (11)
C80.0861 (19)0.0537 (13)0.0563 (14)0.0127 (13)0.0259 (13)0.0379 (12)
C90.0871 (19)0.0386 (11)0.0649 (16)0.0043 (11)0.0202 (14)0.0275 (11)
C100.0680 (15)0.0344 (10)0.0457 (12)0.0062 (10)0.0101 (11)0.0173 (9)
C110.0316 (9)0.0328 (8)0.0269 (8)0.0048 (7)0.0019 (7)0.0114 (7)
C120.0333 (9)0.0443 (10)0.0257 (8)0.0028 (8)0.0006 (7)0.0121 (8)
C130.0400 (11)0.0685 (14)0.0327 (10)0.0056 (10)0.0034 (8)0.0272 (10)
C140.0415 (11)0.0796 (16)0.0490 (12)0.0016 (11)0.0098 (10)0.0400 (12)
C150.0341 (10)0.0678 (14)0.0486 (12)0.0018 (10)0.0052 (9)0.0310 (11)
Geometric parameters (Å, º) top
Cu1—O2i1.9315 (12)C3—C41.416 (2)
Cu1—O11.9434 (11)C3—H30.9300
Cu1—O21.9315 (12)C4—C51.491 (2)
Cu1—O1i1.9434 (11)C5—C61.386 (3)
Cu1—O32.5127 (14)C5—C101.394 (3)
F1A—C11.325 (5)C6—C71.385 (3)
F2A—C11.297 (6)C6—H60.9300
F3A—C11.297 (10)C7—C81.381 (3)
F1B—C11.292 (12)C7—H70.9300
F2B—C11.308 (15)C8—C91.361 (4)
F3B—C11.31 (2)C8—H80.9300
O1—C41.264 (2)C9—C101.385 (3)
O2—C21.277 (2)C9—H90.9300
O3—C111.266 (2)C10—H100.9300
O4—C121.355 (2)C11—C121.436 (2)
O4—H40.8200C12—C131.361 (3)
N1—C111.355 (2)C13—C141.403 (3)
N1—C151.360 (2)C13—H130.9300
N1—H10.8600C14—C151.351 (3)
C1—C21.531 (2)C14—H140.9300
C2—C31.366 (2)C15—H150.9300
O1i—Cu1—O397.30 (5)O1—C4—C5116.62 (16)
O1—Cu1—O382.70 (5)C3—C4—C5120.47 (16)
O2i—Cu1—O2180.00 (6)C6—C5—C10118.77 (17)
O2i—Cu1—O188.07 (5)C6—C5—C4119.01 (16)
O2—Cu1—O191.93 (5)C10—C5—C4122.22 (18)
O2i—Cu1—O1i91.93 (5)C7—C6—C5120.7 (2)
O2—Cu1—O1i88.07 (5)C7—C6—H6119.6
O2—Cu1—O392.53 (5)C5—C6—H6119.6
O2i—Cu1—O387.47 (5)C8—C7—C6119.6 (2)
O1—Cu1—O1i180.0C8—C7—H7120.2
C4—O1—Cu1127.16 (11)C6—C7—H7120.2
C2—O2—Cu1123.14 (11)C9—C8—C7120.2 (2)
C12—O4—H4109.5C9—C8—H8119.9
C11—N1—C15124.59 (16)C7—C8—H8119.9
C11—N1—H1117.7C8—C9—C10120.8 (2)
C15—N1—H1117.7C8—C9—H9119.6
F2A—C1—F3A107.4 (7)C10—C9—H9119.6
F1B—C1—F2B108.5 (13)C9—C10—C5119.9 (2)
F1B—C1—F3B106.5 (14)C9—C10—H10120.1
F2B—C1—F3B106.1 (16)C5—C10—H10120.1
F2A—C1—F1A105.9 (5)O3—C11—N1121.10 (16)
F3A—C1—F1A106.6 (6)O3—C11—C12123.72 (17)
F1B—C1—C2115.2 (7)N1—C11—C12115.18 (16)
F2A—C1—C2112.2 (4)O4—C12—C13120.18 (17)
F3A—C1—C2112.1 (5)O4—C12—C11118.92 (16)
F2B—C1—C2109.7 (9)C13—C12—C11120.89 (18)
F3B—C1—C2110.3 (9)C12—C13—C14120.31 (18)
F1A—C1—C2112.3 (3)C12—C13—H13119.8
O2—C2—C3129.03 (16)C14—C13—H13119.8
O2—C2—C1112.62 (15)C15—C14—C13119.0 (2)
C3—C2—C1118.35 (16)C15—C14—H14120.5
C2—C3—C4123.16 (17)C13—C14—H14120.5
C2—C3—H3118.4C14—C15—N1120.0 (2)
C4—C3—H3118.4C14—C15—H15120.0
O1—C4—C3122.91 (16)N1—C15—H15120.0
Cu1—O2—C2—C34.2 (3)O1—C4—C5—C10173.96 (18)
Cu1—O2—C2—C1175.55 (12)C3—C4—C5—C105.3 (3)
F1B—C1—C2—O2177.4 (18)C10—C5—C6—C70.4 (3)
F2A—C1—C2—O245.2 (7)C4—C5—C6—C7179.44 (19)
F3A—C1—C2—O275.7 (6)C5—C6—C7—C80.1 (4)
F2B—C1—C2—O259.8 (12)C6—C7—C8—C90.2 (4)
F3B—C1—C2—O257 (2)C7—C8—C9—C100.1 (4)
F1A—C1—C2—O2164.4 (5)C8—C9—C10—C50.2 (4)
F1B—C1—C2—C32.4 (18)C6—C5—C10—C90.5 (3)
F2A—C1—C2—C3134.9 (6)C4—C5—C10—C9179.5 (2)
F3A—C1—C2—C3104.1 (6)C15—N1—C11—O3179.61 (19)
F2B—C1—C2—C3120.4 (12)C15—N1—C11—C120.3 (3)
F3B—C1—C2—C3123 (2)O3—C11—C12—O41.9 (3)
F1A—C1—C2—C315.8 (5)N1—C11—C12—O4178.15 (17)
O2—C2—C3—C46.7 (4)O3—C11—C12—C13178.84 (19)
C1—C2—C3—C4173.51 (18)N1—C11—C12—C131.1 (3)
Cu1—O1—C4—C313.0 (3)O4—C12—C13—C14178.6 (2)
Cu1—O1—C4—C5167.84 (12)C11—C12—C13—C140.6 (3)
C2—C3—C4—O12.0 (3)C12—C13—C14—C150.6 (4)
C2—C3—C4—C5177.11 (18)C13—C14—C15—N11.4 (4)
O1—C4—C5—C67.1 (3)C11—N1—C15—C140.9 (4)
C3—C4—C5—C6173.70 (18)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2i0.822.062.8380 (19)160
O4—H4···O30.822.392.7970 (18)111
N1—H1···O3ii0.861.992.842 (2)173
C15—H15···O1iii0.932.483.271 (2)143
C9—H9···O3iv0.932.543.338 (3)144
Symmetry codes: (i) x+1, y, z; (ii) x, y, z; (iii) x1, y, z; (iv) x, y1, z.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds