metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(−)545-fac-Δ-Tris(L-prolinato)cobalt(III) trihydrate

aDepartment of Chemistry, Graduate School of Science and Engineering, Saitama University, Shimo-Okubo 255, Sakura-ku, Saitama 338-8570, Japan, and bMolecular Analysis and Life Science Center, Saitama University, Shimo-Okubo 255, Sakura-ku, Saitama 338-8570, Japan
*Correspondence e-mail: fuji@chem.saitama-u.ac.jp

(Received 12 March 2008; accepted 14 April 2008; online 18 April 2008)

The absolute configuration of the octa­hedral fac-CoN3O3 title complex, [Co(C5H8NO2)3]·3H2O, has been determined by single-crystal X-ray analysis. A three-dimensional network of hydrogen bonds is observed between the proline carboxyl­ate groups and the three uncoordinated water mol­ecules.

Related literature

For related literature, see: Denning & Piper (1965[Denning, R. G. & Piper, T. S. (1965). Inorg. Chem. 5, 1056-1065.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(C5H8NO2)3]·3H2O

  • Mr = 455.35

  • Orthorhombic, P 21 21 21

  • a = 10.1673 (9) Å

  • b = 10.8433 (10) Å

  • c = 17.2157 (14) Å

  • V = 1898.0 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.96 mm−1

  • T = 173 (2) K

  • 0.13 × 0.08 × 0.07 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.885, Tmax = 0.936

  • 13762 measured reflections

  • 4522 independent reflections

  • 2969 reflections with I > 2σ(I)

  • Rint = 0.122

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.107

  • S = 0.92

  • 4522 reflections

  • 274 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.85 e Å−3

  • Δρmin = −0.51 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2596 Friedel pairs

  • Flack parameter: 0.04 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O9—H9D⋯O4i 0.74 (6) 2.19 (7) 2.907 (6) 164 (8)
O8—H8D⋯O2 0.77 (6) 2.11 (6) 2.880 (5) 173 (7)
O7—H7D⋯O9ii 0.66 (7) 2.20 (6) 2.848 (7) 167 (9)
O9—H9C⋯O8 0.77 (6) 2.09 (7) 2.853 (6) 166 (8)
O8—H8C⋯O7 0.93 (6) 1.96 (6) 2.882 (7) 172 (5)
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: SMART-W2K/NT (Bruker, 2003[Bruker (2003). SAINT-W2K/NT and SMART-W2K/NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-W2K/NT (Bruker, 2003[Bruker (2003). SAINT-W2K/NT and SMART-W2K/NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL-NT.

Supporting information


Comment top

The optical activity, absolute configuration, and rearrangement of tris(L-prolinato)cobalt(III) complexes were studied by Denning & Piper (1965), in which the absolute configurations were assigned based on circular dichroism (CD) studies and 1H NMR spectra. In this work, single crystals of the (-)545-fac-[Co(L-pro)3] isomer (I) suitable for single-crystal X-ray analysis have been prepared. This has allowed the determination of the absolute configuration of (I) as Δ. The UV-Vis and CD spectra of (I) in H2O show good agreement with the reported spectra (Denning & Piper, 1965). The molecular structure, Fig. 1, shows three deprotonated proline molecules to chelate the cobalt(III) ion to form octahedral fac-CoN3O3 geometry. The three lattice water form a three-dimensional network of hydrogen bonds with the uncoordinated carbonyl groups of the proline molecules (Table 1 & Fig. 2).

Related literature top

For related literature, see: Denning & Piper (1965).

Experimental top

The title compound was prepared according to the literature method (Denning & Piper, 1965). Single crystals suitable for single-crystal X-ray analysis were obtained by vapor diffusion of ethanol into the aqueous solution of (I) at room temperature. Analysis found: C 39.59, H 6.58, N 9.10; C15H30CoN3O9 C29H34F6O2S2 requires: C 39.57, H 6.64, N 9.23.

Refinement top

The water- and N-bound H atoms were located in difference maps and refined with Uiso(H) = 1.5Ueq(O) or 1.5Ueq(N); see Table 1 for O-H and N-H bond distances. The remaining H atoms were placed in calculated positions, with C—H = 1.00 Å (for CH) and 0.99 Å (for CH2) and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT (Bruker, 2003); program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT (Bruker, 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT (Bruker, 2003).

Figures top
[Figure 1] Fig. 1. ORTEP drawing for (I), showing atom labelling scheme and displacement ellipsoids at the 50% probability level. All hydrogen atoms are omitted for clarity.
[Figure 2] Fig. 2. Three-dimensional network structure of hydrogen bonds viewed in projection down the a axis. Dashed lines indicate the hydrogen-bonding interactions. All hydrogen atoms are omitted for clarity.
(-)545-fac-Δ-Tris(L-prolinato)cobalt(III) trihydrate top
Crystal data top
[Co(C5H8NO2)3]·3H2OF(000) = 960
Mr = 455.35Dx = 1.594 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 705 reflections
a = 10.1673 (9) Åθ = 2.2–17.1°
b = 10.8433 (10) ŵ = 0.96 mm1
c = 17.2157 (14) ÅT = 173 K
V = 1898.0 (3) Å3Block, pink
Z = 40.13 × 0.08 × 0.07 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4522 independent reflections
Radiation source: fine-focus sealed tube2969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.122
Detector resolution: 8.366 pixels mm-1θmax = 27.9°, θmin = 2.2°
ϕ and ω scansh = 137
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.885, Tmax = 0.936l = 2222
13762 measured reflections
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)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0283P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
4522 reflectionsΔρmax = 0.85 e Å3
274 parametersΔρmin = 0.51 e Å3
0 restraintsAbsolute structure: Flack (1983), 2596 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (2)
Crystal data top
[Co(C5H8NO2)3]·3H2OV = 1898.0 (3) Å3
Mr = 455.35Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.1673 (9) ŵ = 0.96 mm1
b = 10.8433 (10) ÅT = 173 K
c = 17.2157 (14) Å0.13 × 0.08 × 0.07 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4522 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2969 reflections with I > 2σ(I)
Tmin = 0.885, Tmax = 0.936Rint = 0.122
13762 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107Δρmax = 0.85 e Å3
S = 0.92Δρmin = 0.51 e Å3
4522 reflectionsAbsolute structure: Flack (1983), 2596 Friedel pairs
274 parametersAbsolute structure parameter: 0.04 (2)
0 restraints
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
C10.3689 (5)0.9795 (5)0.1401 (3)0.0220 (11)
H1A0.43640.93960.10630.026*
C20.4210 (5)1.1046 (5)0.1661 (3)0.0309 (15)
H2A0.39401.12300.22010.037*
H2B0.51821.10740.16270.037*
C30.3589 (5)1.1948 (4)0.1093 (3)0.0248 (11)
H3A0.35611.27940.13090.030*
H3B0.40621.19580.05910.030*
C40.2218 (5)1.1408 (5)0.1008 (3)0.0251 (12)
H4A0.16781.15760.14750.030*
H4B0.17661.17490.05460.030*
C50.3343 (5)0.8910 (5)0.2056 (3)0.0216 (12)
C60.0485 (5)0.7863 (5)0.0354 (3)0.0168 (11)
H6A0.01940.71990.03090.020*
C70.0427 (5)0.8403 (5)0.1185 (3)0.0226 (12)
H7A0.13160.86300.13720.027*
H7B0.00290.78090.15530.027*
C80.0437 (5)0.9539 (4)0.1089 (3)0.0223 (11)
H8A0.02861.01410.15120.027*
H8B0.13810.93160.10740.027*
C90.0024 (5)1.0038 (5)0.0315 (3)0.0213 (12)
H9A0.08931.04420.03640.026*
H9B0.06141.06370.01010.026*
C100.1804 (5)0.7331 (5)0.0136 (3)0.0172 (11)
C110.0584 (5)0.8563 (5)0.2340 (3)0.0208 (12)
H11A0.00410.84480.28190.025*
C120.1937 (5)0.9052 (5)0.2579 (3)0.0311 (15)
H12A0.26430.85980.23050.037*
H12B0.20690.89600.31460.037*
C130.1946 (5)1.0400 (5)0.2351 (3)0.0258 (13)
H13A0.15941.09250.27730.031*
H13B0.28441.06810.22160.031*
C140.1050 (5)1.0419 (5)0.1647 (3)0.0205 (12)
H14A0.15231.01320.11780.025*
H14B0.07101.12610.15510.025*
C150.0597 (5)0.7356 (5)0.1891 (3)0.0180 (11)
Co10.12024 (6)0.87354 (6)0.11104 (3)0.01537 (16)
N10.2469 (4)1.0046 (4)0.0916 (2)0.0190 (10)
H1C0.26980.99570.04700.023*
N20.0110 (4)0.8912 (4)0.01862 (19)0.0144 (9)
H2C0.0700.87570.03380.017*
N30.0039 (4)0.9561 (4)0.1851 (2)0.0194 (11)
H3C0.04600.99000.21080.023*
O10.2224 (3)0.8373 (3)0.20056 (17)0.0198 (9)
O20.4133 (3)0.8715 (4)0.25896 (18)0.0321 (9)
O30.2340 (3)0.7768 (3)0.04792 (18)0.0182 (8)
O40.2308 (3)0.6524 (3)0.05483 (18)0.0275 (9)
O50.0152 (3)0.7314 (3)0.12902 (16)0.0189 (8)
O60.1273 (4)0.6473 (3)0.21062 (17)0.0246 (8)
O70.1135 (5)0.9744 (5)0.4313 (3)0.0419 (12)
H7C0.096 (6)1.024 (6)0.392 (4)0.063*
H7D0.051 (7)0.966 (8)0.442 (4)0.063*
O80.2893 (4)0.7736 (4)0.3961 (2)0.0383 (11)
H8C0.227 (6)0.835 (6)0.404 (3)0.057*
H8D0.328 (6)0.796 (6)0.360 (3)0.057*
O90.3649 (5)0.5837 (4)0.5018 (3)0.0461 (13)
H9C0.356 (8)0.640 (6)0.475 (4)0.069*
H9D0.328 (7)0.531 (6)0.485 (4)0.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.016 (3)0.027 (3)0.023 (2)0.002 (3)0.002 (2)0.003 (2)
C20.024 (3)0.034 (4)0.035 (3)0.010 (3)0.000 (2)0.007 (3)
C30.029 (3)0.019 (3)0.027 (2)0.006 (2)0.009 (3)0.002 (3)
C40.031 (3)0.019 (3)0.025 (3)0.003 (3)0.006 (2)0.004 (3)
C50.028 (3)0.016 (3)0.021 (3)0.005 (2)0.002 (2)0.005 (2)
C60.018 (3)0.018 (3)0.015 (2)0.005 (2)0.004 (2)0.008 (2)
C70.024 (3)0.035 (3)0.009 (2)0.001 (2)0.001 (2)0.002 (2)
C80.019 (3)0.030 (3)0.018 (2)0.000 (2)0.001 (3)0.009 (3)
C90.022 (3)0.018 (3)0.024 (3)0.000 (2)0.000 (2)0.003 (2)
C100.015 (3)0.017 (3)0.019 (3)0.002 (2)0.007 (2)0.001 (2)
C110.028 (3)0.015 (3)0.019 (2)0.001 (3)0.003 (2)0.000 (2)
C120.031 (3)0.025 (4)0.037 (3)0.006 (3)0.014 (3)0.001 (3)
C130.018 (3)0.029 (3)0.030 (3)0.000 (3)0.004 (2)0.003 (3)
C140.022 (3)0.015 (3)0.025 (3)0.003 (3)0.003 (3)0.001 (2)
C150.017 (3)0.018 (3)0.019 (3)0.002 (2)0.006 (2)0.002 (2)
Co10.0161 (3)0.0153 (3)0.0147 (3)0.0008 (3)0.0009 (3)0.0009 (3)
N10.020 (2)0.019 (2)0.018 (2)0.0016 (19)0.0008 (19)0.0008 (17)
N20.013 (2)0.015 (2)0.0159 (19)0.0001 (19)0.0015 (17)0.0004 (18)
N30.026 (3)0.012 (2)0.021 (2)0.004 (2)0.003 (2)0.0027 (18)
O10.021 (2)0.023 (2)0.0158 (17)0.0023 (17)0.0061 (16)0.0040 (15)
O20.033 (2)0.040 (2)0.0236 (18)0.001 (2)0.0133 (16)0.003 (2)
O30.0158 (18)0.019 (2)0.0199 (17)0.0037 (16)0.0049 (15)0.0045 (15)
O40.0225 (19)0.034 (3)0.0261 (19)0.0057 (18)0.0014 (16)0.0104 (18)
O50.0215 (18)0.016 (2)0.0194 (19)0.0054 (16)0.0042 (15)0.0002 (14)
O60.0259 (18)0.021 (2)0.0270 (17)0.005 (2)0.0014 (17)0.0053 (15)
O70.041 (3)0.046 (3)0.039 (2)0.009 (3)0.003 (3)0.0153 (19)
O80.049 (3)0.034 (3)0.032 (2)0.001 (2)0.002 (2)0.004 (2)
O90.048 (3)0.036 (3)0.055 (3)0.005 (3)0.006 (3)0.004 (2)
Geometric parameters (Å, º) top
C1—N11.520 (6)C11—N31.510 (6)
C1—C51.521 (7)C11—C151.520 (7)
C1—C21.523 (7)C11—C121.530 (7)
C1—H1A1.0000C11—H11A1.0000
C2—C31.520 (7)C12—C131.514 (7)
C2—H2A0.9900C12—H12A0.9900
C2—H2B0.9900C12—H12B0.9900
C3—C41.518 (6)C13—C141.516 (6)
C3—H3A0.9900C13—H13A0.9900
C3—H3B0.9900C13—H13B0.9900
C4—N11.507 (6)C14—N31.488 (6)
C4—H4A0.9900C14—H14A0.9900
C4—H4B0.9900C14—H14B0.9900
C5—O21.238 (5)C15—O61.235 (6)
C5—O11.282 (6)C15—O51.285 (5)
C6—C101.508 (6)Co1—O11.900 (3)
C6—N21.518 (6)Co1—O51.900 (3)
C6—C71.546 (6)Co1—O31.903 (3)
C6—H6A1.0000Co1—N11.947 (4)
C7—C81.522 (7)Co1—N21.950 (3)
C7—H7A0.9900Co1—N31.956 (4)
C7—H7B0.9900N1—H1C0.8117
C8—C91.513 (6)N2—H2C0.8806
C8—H8A0.9900N3—H3C0.7180
C8—H8B0.9900O7—H7C0.88 (6)
C9—N21.497 (6)O7—H7D0.66 (7)
C9—H9A0.9900O8—H8C0.93 (6)
C9—H9B0.9900O8—H8D0.77 (6)
C10—O41.237 (6)O9—H9C0.77 (6)
C10—O31.282 (5)O9—H9D0.74 (6)
N1—C1—C5109.4 (4)C13—C12—C11105.7 (4)
N1—C1—C2106.6 (4)C13—C12—H12A110.6
C5—C1—C2115.2 (4)C11—C12—H12A110.6
N1—C1—H1A108.5C13—C12—H12B110.6
C5—C1—H1A108.5C11—C12—H12B110.6
C2—C1—H1A108.5H12A—C12—H12B108.7
C3—C2—C1103.9 (4)C12—C13—C14102.5 (4)
C3—C2—H2A111.0C12—C13—H13A111.3
C1—C2—H2A111.0C14—C13—H13A111.3
C3—C2—H2B111.0C12—C13—H13B111.3
C1—C2—H2B111.0C14—C13—H13B111.3
H2A—C2—H2B109.0H13A—C13—H13B109.2
C4—C3—C2101.3 (4)N3—C14—C13104.5 (4)
C4—C3—H3A111.5N3—C14—H14A110.9
C2—C3—H3A111.5C13—C14—H14A110.9
C4—C3—H3B111.5N3—C14—H14B110.9
C2—C3—H3B111.5C13—C14—H14B110.9
H3A—C3—H3B109.3H14A—C14—H14B108.9
N1—C4—C3103.5 (4)O6—C15—O5123.0 (5)
N1—C4—H4A111.1O6—C15—C11121.3 (4)
C3—C4—H4A111.1O5—C15—C11115.8 (4)
N1—C4—H4B111.1O1—Co1—O590.41 (14)
C3—C4—H4B111.1O1—Co1—O390.97 (14)
H4A—C4—H4B109.0O5—Co1—O389.27 (14)
O2—C5—O1123.3 (5)O1—Co1—N185.92 (15)
O2—C5—C1120.5 (5)O5—Co1—N1172.63 (16)
O1—C5—C1116.2 (4)O3—Co1—N184.41 (15)
C10—C6—N2111.0 (4)O1—Co1—N2173.64 (17)
C10—C6—C7114.1 (4)O5—Co1—N283.85 (15)
N2—C6—C7105.9 (4)O3—Co1—N286.24 (15)
C10—C6—H6A108.6N1—Co1—N299.48 (16)
N2—C6—H6A108.6O1—Co1—N384.07 (15)
C7—C6—H6A108.6O5—Co1—N385.70 (16)
C8—C7—C6103.2 (4)O3—Co1—N3172.90 (16)
C8—C7—H7A111.1N1—Co1—N3100.25 (17)
C6—C7—H7A111.1N2—Co1—N398.17 (16)
C8—C7—H7B111.1C4—N1—C1104.8 (4)
C6—C7—H7B111.1C4—N1—Co1125.9 (3)
H7A—C7—H7B109.1C1—N1—Co1108.3 (3)
C9—C8—C7101.9 (4)C4—N1—H1C105.4
C9—C8—H8A111.4C1—N1—H1C105.4
C7—C8—H8A111.4Co1—N1—H1C105.4
C9—C8—H8B111.4C9—N2—C6105.8 (3)
C7—C8—H8B111.4C9—N2—Co1125.7 (3)
H8A—C8—H8B109.3C6—N2—Co1106.5 (3)
N2—C9—C8103.6 (4)C9—N2—H2C105.8
N2—C9—H9A111.0C6—N2—H2C105.8
C8—C9—H9A111.0Co1—N2—H2C105.8
N2—C9—H9B111.0C14—N3—C11105.5 (4)
C8—C9—H9B111.0C14—N3—Co1125.6 (3)
H9A—C9—H9B109.0C11—N3—Co1106.8 (3)
O4—C10—O3124.0 (5)C14—N3—H3C105.8
O4—C10—C6119.8 (5)C11—N3—H3C105.8
O3—C10—C6116.2 (4)Co1—N3—H3C105.8
N3—C11—C15109.7 (4)C5—O1—Co1116.5 (3)
N3—C11—C12106.2 (4)C10—O3—Co1114.7 (3)
C15—C11—C12115.3 (4)C15—O5—Co1115.8 (3)
N3—C11—H11A108.5H7C—O7—H7D95 (7)
C15—C11—H11A108.5H8C—O8—H8D104 (6)
C12—C11—H11A108.5H9C—O9—H9D108 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9D···O4i0.74 (6)2.19 (7)2.907 (6)164 (8)
O8—H8D···O20.77 (6)2.11 (6)2.880 (5)173 (7)
O7—H7D···O9ii0.66 (7)2.20 (6)2.848 (7)167 (9)
O9—H9C···O80.77 (6)2.09 (7)2.853 (6)166 (8)
O8—H8C···O70.93 (6)1.96 (6)2.882 (7)172 (5)
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x1/2, y+3/2, z+1.

Experimental details

Crystal data
Chemical formula[Co(C5H8NO2)3]·3H2O
Mr455.35
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)10.1673 (9), 10.8433 (10), 17.2157 (14)
V3)1898.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.96
Crystal size (mm)0.13 × 0.08 × 0.07
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.885, 0.936
No. of measured, independent and
observed [I > 2σ(I)] reflections
13762, 4522, 2969
Rint0.122
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.107, 0.92
No. of reflections4522
No. of parameters274
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.85, 0.51
Absolute structureFlack (1983), 2596 Friedel pairs
Absolute structure parameter0.04 (2)

Computer programs: SMART-W2K/NT (Bruker, 2003), SAINT-W2K/NT (Bruker, 2003), SHELXTL-NT (Bruker, 2003), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9D···O4i0.74 (6)2.19 (7)2.907 (6)164 (8)
O8—H8D···O20.77 (6)2.11 (6)2.880 (5)173 (7)
O7—H7D···O9ii0.66 (7)2.20 (6)2.848 (7)167 (9)
O9—H9C···O80.77 (6)2.09 (7)2.853 (6)166 (8)
O8—H8C···O70.93 (6)1.96 (6)2.882 (7)172 (5)
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x1/2, y+3/2, z+1.
 

References

First citationBruker (2003). SAINT-W2K/NT and SMART-W2K/NT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDenning, R. G. & Piper, T. S. (1965). Inorg. Chem. 5, 1056–1065.  CrossRef Web of Science Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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