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

Kato, M.; Hayashi, M.; Fujihara, T.; Nagasawa, A.

doi:10.1107/S1600536808010246

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m684

doi:10.1107/S1600536808010246

Open

access

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

Masaru Kato,^a Miho Hayashi,^a Takashi Fujihara ^b ^* and Akira Nagasawa ^a

^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 ).

Experimental

Crystal data

[Co(C₅H₈NO₂)₃]·3H₂O
M_r = 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 ) T_min = 0.885, T_max = 0.936
13762 measured reflections
4522 independent reflections
2969 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.51 e Å⁻³
Absolute structure: Flack (1983 ), 2596 Friedel pairs
Flack parameter: 0.04 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL-NT.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010246/tk2254sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010246/tk2254Isup2.hkl

checkCIF report

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.

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

	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.
	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]·3H₂O	F(000) = 960
M_r = 455.35	D_x = 1.594 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 705 reflections
a = 10.1673 (9) Å	θ = 2.2–17.1°
b = 10.8433 (10) Å	µ = 0.96 mm⁻¹
c = 17.2157 (14) Å	T = 173 K
V = 1898.0 (3) Å³	Block, pink
Z = 4	0.13 × 0.08 × 0.07 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4522 independent reflections
Radiation source: fine-focus sealed tube	2969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.122
Detector resolution: 8.366 pixels mm^-1	θ_max = 27.9°, θ_min = 2.2°
ϕ and ω scans	h = −13→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
T_min = 0.885, T_max = 0.936	l = −22→22
13762 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0283P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max < 0.001
4522 reflections	Δρ_max = 0.85 e Å⁻³
274 parameters	Δρ_min = −0.51 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2596 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (2)

Crystal data top

[Co(C₅H₈NO₂)₃]·3H₂O	V = 1898.0 (3) Å³
M_r = 455.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.1673 (9) Å	µ = 0.96 mm⁻¹
b = 10.8433 (10) Å	T = 173 K
c = 17.2157 (14) Å	0.13 × 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)
T_min = 0.885, T_max = 0.936	R_int = 0.122
13762 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	Δρ_max = 0.85 e Å⁻³
S = 0.92	Δρ_min = −0.51 e Å⁻³
4522 reflections	Absolute structure: Flack (1983), 2596 Friedel pairs
274 parameters	Absolute 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

	x	y	z	U_iso*/U_eq
C1	0.3689 (5)	0.9795 (5)	0.1401 (3)	0.0220 (11)
H1A	0.4364	0.9396	0.1063	0.026*
C2	0.4210 (5)	1.1046 (5)	0.1661 (3)	0.0309 (15)
H2A	0.3940	1.1230	0.2201	0.037*
H2B	0.5182	1.1074	0.1627	0.037*
C3	0.3589 (5)	1.1948 (4)	0.1093 (3)	0.0248 (11)
H3A	0.3561	1.2794	0.1309	0.030*
H3B	0.4062	1.1958	0.0591	0.030*
C4	0.2218 (5)	1.1408 (5)	0.1008 (3)	0.0251 (12)
H4A	0.1678	1.1576	0.1475	0.030*
H4B	0.1766	1.1749	0.0546	0.030*
C5	0.3343 (5)	0.8910 (5)	0.2056 (3)	0.0216 (12)
C6	0.0485 (5)	0.7863 (5)	−0.0354 (3)	0.0168 (11)
H6A	−0.0194	0.7199	−0.0309	0.020*
C7	0.0427 (5)	0.8403 (5)	−0.1185 (3)	0.0226 (12)
H7A	0.1316	0.8630	−0.1372	0.027*
H7B	0.0029	0.7809	−0.1553	0.027*
C8	−0.0437 (5)	0.9539 (4)	−0.1089 (3)	0.0223 (11)
H8A	−0.0286	1.0141	−0.1512	0.027*
H8B	−0.1381	0.9316	−0.1074	0.027*
C9	0.0024 (5)	1.0038 (5)	−0.0315 (3)	0.0213 (12)
H9A	0.0893	1.0442	−0.0364	0.026*
H9B	−0.0614	1.0637	−0.0101	0.026*
C10	0.1804 (5)	0.7331 (5)	−0.0136 (3)	0.0172 (11)
C11	−0.0584 (5)	0.8563 (5)	0.2340 (3)	0.0208 (12)
H11A	−0.0041	0.8448	0.2819	0.025*
C12	−0.1937 (5)	0.9052 (5)	0.2579 (3)	0.0311 (15)
H12A	−0.2643	0.8598	0.2305	0.037*
H12B	−0.2069	0.8960	0.3146	0.037*
C13	−0.1946 (5)	1.0400 (5)	0.2351 (3)	0.0258 (13)
H13A	−0.1594	1.0925	0.2773	0.031*
H13B	−0.2844	1.0681	0.2216	0.031*
C14	−0.1050 (5)	1.0419 (5)	0.1647 (3)	0.0205 (12)
H14A	−0.1523	1.0132	0.1178	0.025*
H14B	−0.0710	1.1261	0.1551	0.025*
C15	−0.0597 (5)	0.7356 (5)	0.1891 (3)	0.0180 (11)
Co1	0.12024 (6)	0.87354 (6)	0.11104 (3)	0.01537 (16)
N1	0.2469 (4)	1.0046 (4)	0.0916 (2)	0.0190 (10)
H1C	0.2698	0.9957	0.0470	0.023*
N2	0.0110 (4)	0.8912 (4)	0.01862 (19)	0.0144 (9)
H2C	−0.070	0.8757	0.0338	0.017*
N3	0.0039 (4)	0.9561 (4)	0.1851 (2)	0.0194 (11)
H3C	0.0460	0.9900	0.2108	0.023*
O1	0.2224 (3)	0.8373 (3)	0.20056 (17)	0.0198 (9)
O2	0.4133 (3)	0.8715 (4)	0.25896 (18)	0.0321 (9)
O3	0.2340 (3)	0.7768 (3)	0.04792 (18)	0.0182 (8)
O4	0.2308 (3)	0.6524 (3)	−0.05483 (18)	0.0275 (9)
O5	0.0152 (3)	0.7314 (3)	0.12902 (16)	0.0189 (8)
O6	−0.1273 (4)	0.6473 (3)	0.21062 (17)	0.0246 (8)
O7	0.1135 (5)	0.9744 (5)	0.4313 (3)	0.0419 (12)
H7C	0.096 (6)	1.024 (6)	0.392 (4)	0.063*
H7D	0.051 (7)	0.966 (8)	0.442 (4)	0.063*
O8	0.2893 (4)	0.7736 (4)	0.3961 (2)	0.0383 (11)
H8C	0.227 (6)	0.835 (6)	0.404 (3)	0.057*
H8D	0.328 (6)	0.796 (6)	0.360 (3)	0.057*
O9	0.3649 (5)	0.5837 (4)	0.5018 (3)	0.0461 (13)
H9C	0.356 (8)	0.640 (6)	0.475 (4)	0.069*
H9D	0.328 (7)	0.531 (6)	0.485 (4)	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.016 (3)	0.027 (3)	0.023 (2)	−0.002 (3)	0.002 (2)	−0.003 (2)
C2	0.024 (3)	0.034 (4)	0.035 (3)	−0.010 (3)	0.000 (2)	−0.007 (3)
C3	0.029 (3)	0.019 (3)	0.027 (2)	−0.006 (2)	0.009 (3)	−0.002 (3)
C4	0.031 (3)	0.019 (3)	0.025 (3)	0.003 (3)	0.006 (2)	−0.004 (3)
C5	0.028 (3)	0.016 (3)	0.021 (3)	0.005 (2)	0.002 (2)	−0.005 (2)
C6	0.018 (3)	0.018 (3)	0.015 (2)	−0.005 (2)	0.004 (2)	−0.008 (2)
C7	0.024 (3)	0.035 (3)	0.009 (2)	−0.001 (2)	−0.001 (2)	−0.002 (2)
C8	0.019 (3)	0.030 (3)	0.018 (2)	0.000 (2)	−0.001 (3)	0.009 (3)
C9	0.022 (3)	0.018 (3)	0.024 (3)	0.000 (2)	0.000 (2)	0.003 (2)
C10	0.015 (3)	0.017 (3)	0.019 (3)	−0.002 (2)	0.007 (2)	−0.001 (2)
C11	0.028 (3)	0.015 (3)	0.019 (2)	−0.001 (3)	0.003 (2)	0.000 (2)
C12	0.031 (3)	0.025 (4)	0.037 (3)	−0.006 (3)	0.014 (3)	0.001 (3)
C13	0.018 (3)	0.029 (3)	0.030 (3)	0.000 (3)	0.004 (2)	−0.003 (3)
C14	0.022 (3)	0.015 (3)	0.025 (3)	0.003 (3)	−0.003 (3)	0.001 (2)
C15	0.017 (3)	0.018 (3)	0.019 (3)	−0.002 (2)	−0.006 (2)	−0.002 (2)
Co1	0.0161 (3)	0.0153 (3)	0.0147 (3)	−0.0008 (3)	−0.0009 (3)	−0.0009 (3)
N1	0.020 (2)	0.019 (2)	0.018 (2)	0.0016 (19)	−0.0008 (19)	−0.0008 (17)
N2	0.013 (2)	0.015 (2)	0.0159 (19)	0.0001 (19)	−0.0015 (17)	0.0004 (18)
N3	0.026 (3)	0.012 (2)	0.021 (2)	−0.004 (2)	−0.003 (2)	−0.0027 (18)
O1	0.021 (2)	0.023 (2)	0.0158 (17)	0.0023 (17)	−0.0061 (16)	0.0040 (15)
O2	0.033 (2)	0.040 (2)	0.0236 (18)	0.001 (2)	−0.0133 (16)	0.003 (2)
O3	0.0158 (18)	0.019 (2)	0.0199 (17)	0.0037 (16)	−0.0049 (15)	−0.0045 (15)
O4	0.0225 (19)	0.034 (3)	0.0261 (19)	0.0057 (18)	0.0014 (16)	−0.0104 (18)
O5	0.0215 (18)	0.016 (2)	0.0194 (19)	−0.0054 (16)	−0.0042 (15)	−0.0002 (14)
O6	0.0259 (18)	0.021 (2)	0.0270 (17)	−0.005 (2)	−0.0014 (17)	0.0053 (15)
O7	0.041 (3)	0.046 (3)	0.039 (2)	0.009 (3)	−0.003 (3)	0.0153 (19)
O8	0.049 (3)	0.034 (3)	0.032 (2)	−0.001 (2)	0.002 (2)	0.004 (2)
O9	0.048 (3)	0.036 (3)	0.055 (3)	−0.005 (3)	−0.006 (3)	0.004 (2)

Geometric parameters (Å, º) top

C1—N1	1.520 (6)	C11—N3	1.510 (6)
C1—C5	1.521 (7)	C11—C15	1.520 (7)
C1—C2	1.523 (7)	C11—C12	1.530 (7)
C1—H1A	1.0000	C11—H11A	1.0000
C2—C3	1.520 (7)	C12—C13	1.514 (7)
C2—H2A	0.9900	C12—H12A	0.9900
C2—H2B	0.9900	C12—H12B	0.9900
C3—C4	1.518 (6)	C13—C14	1.516 (6)
C3—H3A	0.9900	C13—H13A	0.9900
C3—H3B	0.9900	C13—H13B	0.9900
C4—N1	1.507 (6)	C14—N3	1.488 (6)
C4—H4A	0.9900	C14—H14A	0.9900
C4—H4B	0.9900	C14—H14B	0.9900
C5—O2	1.238 (5)	C15—O6	1.235 (6)
C5—O1	1.282 (6)	C15—O5	1.285 (5)
C6—C10	1.508 (6)	Co1—O1	1.900 (3)
C6—N2	1.518 (6)	Co1—O5	1.900 (3)
C6—C7	1.546 (6)	Co1—O3	1.903 (3)
C6—H6A	1.0000	Co1—N1	1.947 (4)
C7—C8	1.522 (7)	Co1—N2	1.950 (3)
C7—H7A	0.9900	Co1—N3	1.956 (4)
C7—H7B	0.9900	N1—H1C	0.8117
C8—C9	1.513 (6)	N2—H2C	0.8806
C8—H8A	0.9900	N3—H3C	0.7180
C8—H8B	0.9900	O7—H7C	0.88 (6)
C9—N2	1.497 (6)	O7—H7D	0.66 (7)
C9—H9A	0.9900	O8—H8C	0.93 (6)
C9—H9B	0.9900	O8—H8D	0.77 (6)
C10—O4	1.237 (6)	O9—H9C	0.77 (6)
C10—O3	1.282 (5)	O9—H9D	0.74 (6)

N1—C1—C5	109.4 (4)	C13—C12—C11	105.7 (4)
N1—C1—C2	106.6 (4)	C13—C12—H12A	110.6
C5—C1—C2	115.2 (4)	C11—C12—H12A	110.6
N1—C1—H1A	108.5	C13—C12—H12B	110.6
C5—C1—H1A	108.5	C11—C12—H12B	110.6
C2—C1—H1A	108.5	H12A—C12—H12B	108.7
C3—C2—C1	103.9 (4)	C12—C13—C14	102.5 (4)
C3—C2—H2A	111.0	C12—C13—H13A	111.3
C1—C2—H2A	111.0	C14—C13—H13A	111.3
C3—C2—H2B	111.0	C12—C13—H13B	111.3
C1—C2—H2B	111.0	C14—C13—H13B	111.3
H2A—C2—H2B	109.0	H13A—C13—H13B	109.2
C4—C3—C2	101.3 (4)	N3—C14—C13	104.5 (4)
C4—C3—H3A	111.5	N3—C14—H14A	110.9
C2—C3—H3A	111.5	C13—C14—H14A	110.9
C4—C3—H3B	111.5	N3—C14—H14B	110.9
C2—C3—H3B	111.5	C13—C14—H14B	110.9
H3A—C3—H3B	109.3	H14A—C14—H14B	108.9
N1—C4—C3	103.5 (4)	O6—C15—O5	123.0 (5)
N1—C4—H4A	111.1	O6—C15—C11	121.3 (4)
C3—C4—H4A	111.1	O5—C15—C11	115.8 (4)
N1—C4—H4B	111.1	O1—Co1—O5	90.41 (14)
C3—C4—H4B	111.1	O1—Co1—O3	90.97 (14)
H4A—C4—H4B	109.0	O5—Co1—O3	89.27 (14)
O2—C5—O1	123.3 (5)	O1—Co1—N1	85.92 (15)
O2—C5—C1	120.5 (5)	O5—Co1—N1	172.63 (16)
O1—C5—C1	116.2 (4)	O3—Co1—N1	84.41 (15)
C10—C6—N2	111.0 (4)	O1—Co1—N2	173.64 (17)
C10—C6—C7	114.1 (4)	O5—Co1—N2	83.85 (15)
N2—C6—C7	105.9 (4)	O3—Co1—N2	86.24 (15)
C10—C6—H6A	108.6	N1—Co1—N2	99.48 (16)
N2—C6—H6A	108.6	O1—Co1—N3	84.07 (15)
C7—C6—H6A	108.6	O5—Co1—N3	85.70 (16)
C8—C7—C6	103.2 (4)	O3—Co1—N3	172.90 (16)
C8—C7—H7A	111.1	N1—Co1—N3	100.25 (17)
C6—C7—H7A	111.1	N2—Co1—N3	98.17 (16)
C8—C7—H7B	111.1	C4—N1—C1	104.8 (4)
C6—C7—H7B	111.1	C4—N1—Co1	125.9 (3)
H7A—C7—H7B	109.1	C1—N1—Co1	108.3 (3)
C9—C8—C7	101.9 (4)	C4—N1—H1C	105.4
C9—C8—H8A	111.4	C1—N1—H1C	105.4
C7—C8—H8A	111.4	Co1—N1—H1C	105.4
C9—C8—H8B	111.4	C9—N2—C6	105.8 (3)
C7—C8—H8B	111.4	C9—N2—Co1	125.7 (3)
H8A—C8—H8B	109.3	C6—N2—Co1	106.5 (3)
N2—C9—C8	103.6 (4)	C9—N2—H2C	105.8
N2—C9—H9A	111.0	C6—N2—H2C	105.8
C8—C9—H9A	111.0	Co1—N2—H2C	105.8
N2—C9—H9B	111.0	C14—N3—C11	105.5 (4)
C8—C9—H9B	111.0	C14—N3—Co1	125.6 (3)
H9A—C9—H9B	109.0	C11—N3—Co1	106.8 (3)
O4—C10—O3	124.0 (5)	C14—N3—H3C	105.8
O4—C10—C6	119.8 (5)	C11—N3—H3C	105.8
O3—C10—C6	116.2 (4)	Co1—N3—H3C	105.8
N3—C11—C15	109.7 (4)	C5—O1—Co1	116.5 (3)
N3—C11—C12	106.2 (4)	C10—O3—Co1	114.7 (3)
C15—C11—C12	115.3 (4)	C15—O5—Co1	115.8 (3)
N3—C11—H11A	108.5	H7C—O7—H7D	95 (7)
C15—C11—H11A	108.5	H8C—O8—H8D	104 (6)
C12—C11—H11A	108.5	H9C—O9—H9D	108 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, −y+1, z+1/2; (ii) x−1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₅H₈NO₂)₃]·3H₂O
M_r	455.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	10.1673 (9), 10.8433 (10), 17.2157 (14)
V (Å³)	1898.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.96
Crystal size (mm)	0.13 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.885, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	13762, 4522, 2969
R_int	0.122
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.107, 0.92
No. of reflections	4522
No. of parameters	274
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.51
Absolute structure	Flack (1983), 2596 Friedel pairs
Absolute structure parameter	0.04 (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···A	D—H	H···A	D···A	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+1/2, −y+1, z+1/2; (ii) x−1/2, −y+3/2, −z+1.

References

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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m684

doi:10.1107/S1600536808010246

Open

access