A one-dimensional coordination polymer constructed from isatine-3-oximate and sodium

Barreto Martins, B.; Bresolin, L.; Santana Carratu, V.; Boneberger Behm, M.; Bof de Oliveira, A.

doi:10.1107/S1600536811018290

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m790-m791

doi:10.1107/S1600536811018290

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A one-dimensional coordination polymer constructed from isatine-3-oximate and sodium

Bianca Barreto Martins,^a Leandro Bresolin,^a Vanessa Santana Carratu,^a ^* Mariana Boneberger Behm ^b and Adriano Bof de Oliveira ^c

^aEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96201-900 Rio Grande, RS, Brazil, ^bDepartamento de Química, Universidade Federal de Santa Maria, Av. Roraima, Campus, 97105-900 Santa Maria, RS, Brazil, and ^cDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão, SE, Brazil
^*Correspondence e-mail: vanessa_carratu@yahoo.com.br

(Received 16 April 2011; accepted 13 May 2011; online 25 May 2011)

The reaction of hydroxylamine hydrochloride with isatin in ethanol, catalysed with HCl and neutralized with Na₂CO₃, yielded the one-dimensional coordination polymer, catena-poly[[[aquasodium]-di-μ-aqua-[aquasodium]-bis(μ-2-oxoindoline-2,3-dione 3-oximato)] tetrakis(oxoindoline-2,3-dione 3-oxime)], {[Na(C₈H₅N₂O₂)(H₂O)₂]·2C₈H₆N₂O₂}_n. The Na^I atom has a six-coordinate distorted-octahedral environment. Isatine-3-oximate O atoms and water molecules bridge adjacent Na atoms, forming a one-dimensional polymeric structure parallel to [100]. Each isatine-3-oxime dimerizes through N—H⋯O interactions and in addition each oxime is linked to a coordination polymer. Thus, coordination polymers are linked by O—H⋯O and O—H⋯N interactions from isatine-3-oxime dimers, building a two-dimensional network parallel to [110].

Related literature

For the pharmacological and biological properties of oxime derivatives, see: Chafeev et al. (2008 ). For the preparation and characterization of some metal complexes of isatine-3-oxime, see: Hudák & Košturiak (1999 ).

Experimental

Crystal data

[Na(C₈H₅N₂O₂)(H₂O)₂]·2C₈H₆N₂O₂
M_r = 544.45
Triclinic, $[P \overline 1]$
a = 7.2987 (3) Å
b = 11.9269 (5) Å
c = 15.0756 (6) Å
α = 95.369 (2)°
β = 102.871 (2)°
γ = 102.631 (2)°
V = 1234.36 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.74 × 0.23 × 0.18 mm

Data collection

Bruker CCD X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.912, T_max = 0.978
25159 measured reflections
7175 independent reflections
4225 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.135
S = 1.04
7175 reflections
388 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21—H21⋯O21ⁱ	0.87 (2)	1.97 (2)	2.846 (5)	175 (2)
O22—H22⋯O12	0.94 (2)	1.70 (2)	2.633 (3)	171 (2)
O22—H22⋯N12	0.94 (2)	2.45 (2)	3.226 (4)	140 (2)
Symmetry code: (i) -x-1, -y, -z.

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018290/bt5520sup1.cif

Supporting information file. DOI: 10.1107/S1600536811018290/bt5520Isup2.mol

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018290/bt5520Isup3.hkl

checkCIF report

Comment top

Oxime derivatives such as isatine-3-oxime have a wide range of properties. For example, they modulate ion flux through a voltage-dependent sodium channel in a mammal. Acting as small molecule sodium channel blockers, these compounds are used intreating diseases or conditions such as hypercholesterolemia and cancer (Chafeev et al., 2008). As part of our interest in the study of oxime derivatives, we report herein the crystal structure of [Na(C₈N₂O₂H₅)(H₂O)₂](C₈N₂O₂H₆)₂. Crystallographically independent, the structure contains two protonated isatine-3-oxime, two water molecules, one isatine-3-oximate and one sodium(I). The sodium cation has a six-coordinate distorted octahedral environment: one ON-donor bidentate oximate and two water molecules are crystallographically independent. One O-donor monodentate oximate, symmetry generatedⁱⁱ, and one symmetry generated water moleculeⁱ complete the coordination sphere. The polymeric structure is build one side with two bridging water molecules, one crystallographicaly independent and one symmetry generatedⁱ and another side with one bridging oxygen atom from a crystallographically independent oximate and one oxygen atom from a symmetry generatedⁱⁱ oximate. These O-donor bridging atoms form a 1-D zigzag chain of Na complexes in solid state. For the sodium(I) coordination sphere the metal-donor distances [Å] are: Na—O11 = 2,5721 (14), Na—O11ⁱⁱ = 2,3281 (14), Na—O2W = 2,361 (2), Na—O1W = 2,4117 (17), Na—O1Wⁱ = 2,485 (18), Na—N12 = 2,4906 (15). Selected angles (°) are: O1Wⁱ—Na—O11 = 158,74 (6), O2W—Na—O1W = 162,92 (8), O11ⁱⁱ—Na—N12 = 141,63 (6) and build a distorced octahedra. Symmetry codes: (i)-x,-y + 1,-z; (ii)-x + 1,-y + 1,-z.

Related literature top

For the pharmacological and biological properties of oxime derivatives, see: Chafeev et al. (2008). For the preparation and characterization of some metal complexes of isatine-3-oxime, see: Hudák & Košturiak (1999).

Experimental top

Starting materials were commercially available and were used without further purification. The synthesis was adapted from a procedure reported previously (Chafeev et al., 2008; Hudák & Košturiak, 1999). The hydrochloric acid catalyzed reaction of isatin (8,83 mmol) and hydroxylamine hydrochloride (8,83 mmol) in ethanol (50 ml) was refluxed for 6 h and neutralized with a 10% solution of sodium carbonate in water (50 ml). After cooling and filtering, crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. : The molecular structure of [Na(C₈N₂O₂H₅)(H₂O)₂](C₈N₂O₂H₆)₂ with 40% probability displacement ellipsoids for non-H atoms.
	Fig. 2. : The one-dimensional sodium(I) coordination polymer along a axis. The graphical representation is simplified for clarity.

catena-poly[[[aquasodium]-di-µ-aqua-[aquasodium]-bis(µ-2- oxoindoline-2,3-dione 3-oximato)] tetrakis(oxoindoline-2,3-dione 3-oxime)] top

Crystal data top

[Na(C₈H₅N₂O₂)(H₂O)₂]·2C₈H₆N₂O₂	Z = 2
M_r = 544.45	F(000) = 564
Triclinic, P1	D_x = 1.465 Mg m⁻³
Hall symbol: -P 1	Melting point: 507 K
a = 7.2987 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9269 (5) Å	Cell parameters from 25159 reflections
c = 15.0756 (6) Å	θ = 2.1–30.1°
α = 95.369 (2)°	µ = 0.13 mm⁻¹
β = 102.871 (2)°	T = 293 K
γ = 102.631 (2)°	Block, yellow
V = 1234.36 (9) Å³	0.74 × 0.23 × 0.18 mm

Data collection top

Bruker CCD X8 APEXII diffractometer	7175 independent reflections
Radiation source: fine-focus sealed tube, CCD area detector	4225 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −8→10
T_min = 0.912, T_max = 0.978	k = −16→16
25159 measured reflections	l = −21→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0563P)² + 0.222P] where P = (F_o² + 2F_c²)/3
7175 reflections	(Δ/σ)_max = 0.002
388 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Na(C₈H₅N₂O₂)(H₂O)₂]·2C₈H₆N₂O₂	γ = 102.631 (2)°
M_r = 544.45	V = 1234.36 (9) Å³
Triclinic, P1	Z = 2
a = 7.2987 (3) Å	Mo Kα radiation
b = 11.9269 (5) Å	µ = 0.13 mm⁻¹
c = 15.0756 (6) Å	T = 293 K
α = 95.369 (2)°	0.74 × 0.23 × 0.18 mm
β = 102.871 (2)°

Data collection top

Bruker CCD X8 APEXII diffractometer	7175 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	4225 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.978	R_int = 0.029
25159 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.34 e Å⁻³
7175 reflections	Δρ_min = −0.35 e Å⁻³
388 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
O1W	0.0994 (2)	0.63158 (15)	0.01259 (17)	0.0687 (5)
O2W	0.3016 (4)	0.28216 (19)	0.02320 (19)	0.1066 (8)
H1WA	0.130 (5)	0.663 (3)	−0.029 (3)	0.129 (15)*
H1WB	0.119 (6)	0.683 (3)	0.063 (3)	0.143 (16)*
H2WB	0.198 (5)	0.225 (3)	−0.008 (2)	0.104 (11)*
H11	0.940 (3)	0.5518 (17)	0.2221 (14)	0.058 (6)*
H21	−0.432 (3)	−0.0502 (18)	0.0682 (15)	0.058 (6)*
H22	0.101 (3)	0.409 (2)	0.2678 (15)	0.072 (7)*
H31	0.157 (3)	0.100 (2)	0.0853 (17)	0.071 (7)*
H32	0.264 (4)	−0.314 (3)	0.283 (2)	0.109 (10)*
H2WA	0.412 (6)	0.258 (3)	0.023 (3)	0.157 (15)*
Na	0.24999 (10)	0.47107 (6)	0.02804 (5)	0.04703 (19)
C11	0.6536 (2)	0.53381 (15)	0.18198 (12)	0.0393 (4)
C12	0.5139 (2)	0.54630 (13)	0.23926 (11)	0.0322 (3)
C13	0.6261 (2)	0.57694 (13)	0.33425 (10)	0.0307 (3)
C14	0.5812 (2)	0.60035 (15)	0.41768 (11)	0.0405 (4)
H14	0.4542	0.5980	0.4200	0.049*
C15	0.7296 (3)	0.62728 (16)	0.49741 (12)	0.0474 (4)
H15	0.7017	0.6430	0.5539	0.057*
C16	0.9194 (3)	0.63120 (17)	0.49426 (12)	0.0473 (4)
H16	1.0167	0.6498	0.5487	0.057*
C17	0.9670 (2)	0.60815 (16)	0.41194 (12)	0.0432 (4)
H17	1.0943	0.6110	0.4100	0.052*
C18	0.8188 (2)	0.58075 (13)	0.33264 (11)	0.0328 (3)
N11	0.83052 (19)	0.55582 (13)	0.24153 (10)	0.0405 (3)
N12	0.33205 (18)	0.52849 (12)	0.19803 (9)	0.0358 (3)
O11	0.61709 (18)	0.50974 (14)	0.09817 (9)	0.0622 (4)
O12	0.21617 (15)	0.54444 (9)	0.25488 (8)	0.0371 (3)
C21	−0.3048 (2)	0.11666 (15)	0.10061 (13)	0.0418 (4)
C22	−0.1543 (2)	0.17741 (14)	0.18624 (12)	0.0374 (4)
C23	−0.1264 (2)	0.09011 (14)	0.24606 (12)	0.0378 (4)
C24	−0.0120 (3)	0.09265 (16)	0.33278 (13)	0.0453 (4)
H24	0.0701	0.1619	0.3660	0.054*
C25	−0.0219 (3)	−0.01047 (18)	0.36947 (14)	0.0530 (5)
H25	0.0546	−0.0103	0.4278	0.064*
C26	−0.1445 (3)	−0.11327 (18)	0.32007 (16)	0.0592 (5)
H26	−0.1499	−0.1811	0.3463	0.071*
C27	−0.2593 (3)	−0.11803 (16)	0.23284 (15)	0.0522 (5)
H27	−0.3406	−0.1877	0.1999	0.063*
C28	−0.2488 (2)	−0.01592 (14)	0.19665 (12)	0.0401 (4)
C31	0.1466 (3)	−0.05497 (19)	0.11845 (18)	0.0596 (6)
C32	0.2434 (3)	−0.09228 (16)	0.20606 (15)	0.0520 (5)
C33	0.3592 (3)	0.01207 (16)	0.26774 (16)	0.0527 (5)
C34	0.4738 (3)	0.03367 (19)	0.35712 (19)	0.0662 (6)
H34	0.4890	−0.0271	0.3902	0.079*
C35	0.5659 (3)	0.1486 (2)	0.3964 (2)	0.0780 (8)
H35	0.6428	0.1653	0.4565	0.094*
C36	0.5420 (4)	0.2381 (2)	0.3453 (3)	0.0875 (9)
H36	0.6042	0.3143	0.3723	0.105*
C37	0.4292 (4)	0.2177 (2)	0.2559 (2)	0.0790 (8)
H37	0.4154	0.2784	0.2226	0.095*
C38	0.3383 (3)	0.10472 (17)	0.2184 (2)	0.0658 (7)
N21	−0.3501 (2)	0.00296 (13)	0.11123 (11)	0.0456 (4)
N22	−0.0782 (2)	0.28682 (12)	0.19124 (10)	0.0413 (3)
N31	0.2124 (3)	0.06162 (17)	0.12979 (17)	0.0685 (5)
N32	0.2115 (2)	−0.20215 (13)	0.20959 (12)	0.0518 (4)
O21	−0.37599 (19)	0.15939 (11)	0.03390 (9)	0.0522 (3)
O22	0.05472 (18)	0.33089 (11)	0.27387 (9)	0.0472 (3)
O31	0.0319 (3)	−0.11626 (16)	0.05048 (13)	0.0772 (5)
O32	0.3051 (2)	−0.22606 (12)	0.29317 (10)	0.0575 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.0589 (9)	0.0549 (9)	0.1021 (15)	0.0188 (7)	0.0294 (10)	0.0270 (10)
O2W	0.0800 (14)	0.0787 (14)	0.154 (2)	0.0381 (12)	0.0035 (14)	0.0028 (13)
Na	0.0443 (4)	0.0630 (5)	0.0378 (4)	0.0207 (3)	0.0113 (3)	0.0064 (3)
C11	0.0309 (8)	0.0550 (10)	0.0342 (9)	0.0132 (7)	0.0100 (7)	0.0075 (8)
C12	0.0262 (7)	0.0374 (8)	0.0347 (8)	0.0082 (6)	0.0102 (6)	0.0063 (7)
C13	0.0262 (7)	0.0334 (8)	0.0329 (8)	0.0075 (6)	0.0076 (6)	0.0054 (6)
C14	0.0317 (8)	0.0530 (10)	0.0376 (9)	0.0104 (7)	0.0116 (7)	0.0033 (8)
C15	0.0464 (10)	0.0597 (11)	0.0331 (9)	0.0094 (8)	0.0108 (8)	−0.0002 (8)
C16	0.0408 (9)	0.0604 (12)	0.0340 (9)	0.0107 (8)	0.0001 (7)	0.0010 (8)
C17	0.0288 (8)	0.0564 (11)	0.0432 (10)	0.0130 (7)	0.0044 (7)	0.0064 (8)
C18	0.0278 (7)	0.0371 (8)	0.0346 (9)	0.0095 (6)	0.0081 (6)	0.0063 (7)
N11	0.0269 (7)	0.0619 (9)	0.0366 (8)	0.0163 (6)	0.0111 (6)	0.0060 (7)
N12	0.0275 (6)	0.0435 (8)	0.0380 (8)	0.0098 (5)	0.0099 (6)	0.0069 (6)
O11	0.0414 (7)	0.1127 (12)	0.0331 (7)	0.0220 (7)	0.0103 (6)	0.0050 (7)
O12	0.0284 (5)	0.0396 (6)	0.0454 (7)	0.0076 (4)	0.0150 (5)	0.0039 (5)
C21	0.0382 (9)	0.0400 (9)	0.0480 (11)	0.0101 (7)	0.0132 (8)	0.0045 (8)
C22	0.0366 (8)	0.0348 (9)	0.0428 (9)	0.0083 (7)	0.0148 (7)	0.0053 (7)
C23	0.0360 (8)	0.0373 (9)	0.0438 (10)	0.0096 (7)	0.0168 (7)	0.0063 (7)
C24	0.0440 (10)	0.0463 (10)	0.0483 (11)	0.0109 (8)	0.0171 (8)	0.0078 (8)
C25	0.0554 (11)	0.0605 (12)	0.0526 (12)	0.0215 (10)	0.0201 (9)	0.0222 (10)
C26	0.0672 (13)	0.0481 (12)	0.0761 (15)	0.0221 (10)	0.0308 (12)	0.0273 (11)
C27	0.0545 (11)	0.0379 (10)	0.0676 (13)	0.0108 (8)	0.0220 (10)	0.0097 (9)
C28	0.0379 (9)	0.0372 (9)	0.0484 (10)	0.0102 (7)	0.0171 (8)	0.0052 (7)
C31	0.0543 (12)	0.0544 (13)	0.0858 (17)	0.0220 (10)	0.0372 (12)	0.0205 (12)
C32	0.0481 (10)	0.0448 (11)	0.0757 (14)	0.0168 (8)	0.0330 (10)	0.0160 (10)
C33	0.0461 (10)	0.0437 (10)	0.0800 (15)	0.0157 (8)	0.0342 (11)	0.0123 (10)
C34	0.0555 (12)	0.0521 (12)	0.1007 (19)	0.0148 (10)	0.0384 (13)	0.0098 (12)
C35	0.0565 (13)	0.0603 (15)	0.114 (2)	0.0060 (11)	0.0333 (14)	−0.0109 (14)
C36	0.0672 (16)	0.0467 (14)	0.155 (3)	0.0080 (11)	0.0546 (19)	−0.0051 (16)
C37	0.0702 (16)	0.0471 (13)	0.138 (3)	0.0199 (11)	0.0569 (17)	0.0200 (15)
C38	0.0596 (13)	0.0445 (11)	0.117 (2)	0.0228 (10)	0.0553 (14)	0.0232 (12)
N21	0.0433 (8)	0.0373 (8)	0.0513 (10)	0.0052 (7)	0.0095 (7)	0.0003 (7)
N22	0.0384 (7)	0.0405 (8)	0.0435 (8)	0.0068 (6)	0.0108 (6)	0.0048 (6)
N31	0.0694 (12)	0.0609 (12)	0.0961 (17)	0.0297 (10)	0.0420 (12)	0.0323 (12)
N32	0.0481 (9)	0.0467 (9)	0.0694 (11)	0.0156 (7)	0.0258 (8)	0.0156 (8)
O21	0.0544 (8)	0.0479 (7)	0.0498 (8)	0.0116 (6)	0.0047 (6)	0.0080 (6)
O22	0.0483 (7)	0.0390 (7)	0.0474 (8)	0.0021 (6)	0.0062 (6)	0.0068 (6)
O31	0.0769 (11)	0.0799 (11)	0.0826 (12)	0.0274 (9)	0.0238 (10)	0.0229 (10)
O32	0.0594 (8)	0.0453 (8)	0.0695 (10)	0.0120 (6)	0.0191 (7)	0.0126 (7)

Geometric parameters (Å, º) top

O1W—Na	2.4117 (17)	C22—N22	1.290 (2)
O1W—Naⁱ	2.4851 (18)	C22—C23	1.458 (2)
O1W—H1WA	0.80 (4)	C23—C24	1.379 (3)
O1W—H1WB	0.89 (4)	C23—C28	1.409 (2)
O2W—Na	2.361 (2)	C24—C25	1.389 (3)
O2W—H2WB	0.90 (3)	C24—H24	0.9300
O2W—H2WA	0.92 (4)	C25—C26	1.382 (3)
Na—O11ⁱⁱ	2.3281 (14)	C25—H25	0.9300
Na—O1Wⁱ	2.4851 (18)	C26—C27	1.382 (3)
Na—N12	2.4906 (15)	C26—H26	0.9300
Na—O11	2.5721 (14)	C27—C28	1.374 (3)
Na—Naⁱ	3.7874 (13)	C27—H27	0.9300
Na—Naⁱⁱ	3.8590 (13)	C28—N21	1.400 (2)
C11—O11	1.224 (2)	C31—O31	1.223 (3)
C11—N11	1.354 (2)	C31—N31	1.349 (3)
C11—C12	1.497 (2)	C31—C32	1.508 (3)
C12—N12	1.2954 (19)	C32—N32	1.288 (2)
C12—C13	1.450 (2)	C32—C33	1.450 (3)
C13—C14	1.387 (2)	C33—C34	1.386 (3)
C13—C18	1.403 (2)	C33—C38	1.405 (3)
C14—C15	1.384 (2)	C34—C35	1.396 (3)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.388 (3)	C35—C36	1.393 (4)
C15—H15	0.9300	C35—H35	0.9300
C16—C17	1.380 (2)	C36—C37	1.382 (4)
C16—H16	0.9300	C36—H36	0.9300
C17—C18	1.379 (2)	C37—C38	1.370 (3)
C17—H17	0.9300	C37—H37	0.9300
C18—N11	1.403 (2)	C38—N31	1.418 (3)
N11—H11	0.92 (2)	N21—H21	0.88 (2)
N12—O12	1.3598 (16)	N22—O22	1.3730 (19)
O11—Naⁱⁱ	2.3281 (14)	N31—H31	0.92 (2)
C21—O21	1.233 (2)	N32—O32	1.380 (2)
C21—N21	1.357 (2)	O22—H22	0.94 (2)
C21—C22	1.498 (2)	O32—H32	1.01 (3)

Na—O1W—Naⁱ	101.31 (6)	C12—N12—O12	114.48 (13)
Na—O1W—H1WA	108 (3)	C12—N12—Na	115.23 (10)
Naⁱ—O1W—H1WA	112 (3)	O12—N12—Na	130.29 (9)
Na—O1W—H1WB	118 (2)	C11—O11—Naⁱⁱ	143.47 (12)
Naⁱ—O1W—H1WB	106 (3)	C11—O11—Na	110.20 (10)
H1WA—O1W—H1WB	111 (3)	Naⁱⁱ—O11—Na	103.80 (5)
Na—O2W—H2WB	114.6 (19)	O21—C21—N21	126.21 (17)
Na—O2W—H2WA	130 (3)	O21—C21—C22	128.03 (16)
H2WB—O2W—H2WA	109 (3)	N21—C21—C22	105.76 (15)
O11ⁱⁱ—Na—O2W	87.67 (8)	N22—C22—C23	134.90 (16)
O11ⁱⁱ—Na—O1W	96.19 (7)	N22—C22—C21	118.13 (16)
O2W—Na—O1W	162.92 (8)	C23—C22—C21	106.95 (14)
O11ⁱⁱ—Na—O1Wⁱ	114.02 (7)	C24—C23—C28	119.79 (16)
O2W—Na—O1Wⁱ	84.53 (8)	C24—C23—C22	134.28 (16)
O1W—Na—O1Wⁱ	78.69 (6)	C28—C23—C22	105.92 (15)
O11ⁱⁱ—Na—N12	141.63 (5)	C23—C24—C25	118.61 (18)
O2W—Na—N12	99.06 (8)	C23—C24—H24	120.7
O1W—Na—N12	88.24 (7)	C25—C24—H24	120.7
O1Wⁱ—Na—N12	104.24 (7)	C26—C25—C24	120.6 (2)
O11ⁱⁱ—Na—O11	76.20 (5)	C26—C25—H25	119.7
O2W—Na—O11	77.10 (7)	C24—C25—H25	119.7
O1W—Na—O11	119.99 (6)	C27—C26—C25	121.82 (19)
O1Wⁱ—Na—O11	158.74 (6)	C27—C26—H26	119.1
N12—Na—O11	68.78 (4)	C25—C26—H26	119.1
O11ⁱⁱ—Na—Naⁱ	109.62 (5)	C28—C27—C26	117.46 (18)
O2W—Na—Naⁱ	123.11 (7)	C28—C27—H27	121.3
O1W—Na—Naⁱ	40.05 (4)	C26—C27—H27	121.3
O1Wⁱ—Na—Naⁱ	38.64 (4)	C27—C28—N21	128.73 (17)
N12—Na—Naⁱ	98.16 (4)	C27—C28—C23	121.74 (18)
O11—Na—Naⁱ	158.40 (5)	N21—C28—C23	109.52 (15)
O11ⁱⁱ—Na—Naⁱⁱ	40.34 (3)	O31—C31—N31	126.3 (2)
O2W—Na—Naⁱⁱ	80.01 (7)	O31—C31—C32	127.9 (2)
O1W—Na—Naⁱⁱ	113.47 (5)	N31—C31—C32	105.8 (2)
O1Wⁱ—Na—Naⁱⁱ	150.08 (7)	N32—C32—C33	135.3 (2)
N12—Na—Naⁱⁱ	103.40 (4)	N32—C32—C31	117.4 (2)
O11—Na—Naⁱⁱ	35.87 (3)	C33—C32—C31	107.33 (17)
Naⁱ—Na—Naⁱⁱ	145.31 (4)	C34—C33—C38	120.1 (2)
O11—C11—N11	126.48 (15)	C34—C33—C32	134.14 (19)
O11—C11—C12	127.36 (14)	C38—C33—C32	105.8 (2)
N11—C11—C12	106.15 (14)	C33—C34—C35	118.6 (2)
N12—C12—C13	134.80 (14)	C33—C34—H34	120.7
N12—C12—C11	118.35 (14)	C35—C34—H34	120.7
C13—C12—C11	106.84 (12)	C36—C35—C34	119.7 (3)
C14—C13—C18	119.60 (14)	C36—C35—H35	120.2
C14—C13—C12	134.32 (14)	C34—C35—H35	120.2
C18—C13—C12	106.07 (13)	C37—C36—C35	122.3 (2)
C15—C14—C13	118.58 (15)	C37—C36—H36	118.9
C15—C14—H14	120.7	C35—C36—H36	118.9
C13—C14—H14	120.7	C38—C37—C36	117.5 (3)
C14—C15—C16	120.90 (16)	C38—C37—H37	121.3
C14—C15—H15	119.5	C36—C37—H37	121.3
C16—C15—H15	119.5	C37—C38—C33	121.9 (3)
C17—C16—C15	121.37 (16)	C37—C38—N31	128.3 (2)
C17—C16—H16	119.3	C33—C38—N31	109.82 (19)
C15—C16—H16	119.3	C21—N21—C28	111.79 (15)
C18—C17—C16	117.64 (15)	C21—N21—H21	122.1 (14)
C18—C17—H17	121.2	C28—N21—H21	126.1 (14)
C16—C17—H17	121.2	C22—N22—O22	111.60 (14)
C17—C18—C13	121.90 (15)	C31—N31—C38	111.2 (2)
C17—C18—N11	128.29 (14)	C31—N31—H31	117.4 (15)
C13—C18—N11	109.79 (13)	C38—N31—H31	130.6 (15)
C11—N11—C18	111.13 (13)	C32—N32—O32	112.35 (17)
C11—N11—H11	122.0 (13)	N22—O22—H22	102.9 (14)
C18—N11—H11	126.9 (13)	N32—O32—H32	100.8 (16)

Naⁱ—O1W—Na—O11ⁱⁱ	113.32 (8)	Naⁱⁱ—Na—O11—C11	166.41 (17)
Naⁱ—O1W—Na—O2W	11.0 (4)	O11ⁱⁱ—Na—O11—Naⁱⁱ	0.0
Naⁱ—O1W—Na—O1Wⁱ	0.0	O2W—Na—O11—Naⁱⁱ	90.76 (9)
Naⁱ—O1W—Na—N12	−104.90 (8)	O1W—Na—O11—Naⁱⁱ	−89.23 (9)
Naⁱ—O1W—Na—O11	−169.06 (6)	O1Wⁱ—Na—O11—Naⁱⁱ	121.64 (19)
Naⁱ—O1W—Na—Naⁱⁱ	151.25 (6)	N12—Na—O11—Naⁱⁱ	−164.04 (8)
O11—C11—C12—N12	1.2 (3)	Naⁱ—Na—O11—Naⁱⁱ	−108.60 (12)
N11—C11—C12—N12	−179.47 (14)	O21—C21—C22—N22	−4.4 (3)
O11—C11—C12—C13	−179.19 (18)	N21—C21—C22—N22	176.21 (14)
N11—C11—C12—C13	0.14 (18)	O21—C21—C22—C23	177.07 (17)
N12—C12—C13—C14	−0.9 (3)	N21—C21—C22—C23	−2.36 (17)
C11—C12—C13—C14	179.58 (18)	N22—C22—C23—C24	2.9 (3)
N12—C12—C13—C18	178.88 (17)	C21—C22—C23—C24	−178.91 (18)
C11—C12—C13—C18	−0.64 (17)	N22—C22—C23—C28	−176.34 (18)
C18—C13—C14—C15	0.2 (2)	C21—C22—C23—C28	1.88 (17)
C12—C13—C14—C15	179.93 (17)	C28—C23—C24—C25	−0.4 (2)
C13—C14—C15—C16	0.2 (3)	C22—C23—C24—C25	−179.56 (17)
C14—C15—C16—C17	−0.2 (3)	C23—C24—C25—C26	−0.2 (3)
C15—C16—C17—C18	−0.1 (3)	C24—C25—C26—C27	0.8 (3)
C16—C17—C18—C13	0.5 (3)	C25—C26—C27—C28	−0.6 (3)
C16—C17—C18—N11	178.98 (17)	C26—C27—C28—N21	−179.25 (17)
C14—C13—C18—C17	−0.5 (2)	C26—C27—C28—C23	−0.1 (3)
C12—C13—C18—C17	179.66 (15)	C24—C23—C28—C27	0.6 (2)
C14—C13—C18—N11	−179.26 (14)	C22—C23—C28—C27	179.98 (15)
C12—C13—C18—N11	0.91 (17)	C24—C23—C28—N21	179.90 (15)
O11—C11—N11—C18	179.77 (18)	C22—C23—C28—N21	−0.75 (18)
C12—C11—N11—C18	0.43 (19)	O31—C31—C32—N32	4.0 (3)
C17—C18—N11—C11	−179.51 (17)	N31—C31—C32—N32	−176.08 (16)
C13—C18—N11—C11	−0.87 (19)	O31—C31—C32—C33	−177.3 (2)
C13—C12—N12—O12	2.1 (3)	N31—C31—C32—C33	2.7 (2)
C11—C12—N12—O12	−178.47 (13)	N32—C32—C33—C34	−3.9 (4)
C13—C12—N12—Na	−178.03 (15)	C31—C32—C33—C34	177.7 (2)
C11—C12—N12—Na	1.44 (18)	N32—C32—C33—C38	176.3 (2)
O11ⁱⁱ—Na—N12—C12	−27.44 (16)	C31—C32—C33—C38	−2.16 (19)
O2W—Na—N12—C12	70.32 (13)	C38—C33—C34—C35	0.3 (3)
O1W—Na—N12—C12	−125.20 (12)	C32—C33—C34—C35	−179.50 (19)
O1Wⁱ—Na—N12—C12	156.94 (11)	C33—C34—C35—C36	−0.4 (3)
O11—Na—N12—C12	−1.95 (11)	C34—C35—C36—C37	0.0 (3)
Naⁱ—Na—N12—C12	−164.11 (11)	C35—C36—C37—C38	0.5 (3)
Naⁱⁱ—Na—N12—C12	−11.48 (12)	C36—C37—C38—C33	−0.6 (3)
O11ⁱⁱ—Na—N12—O12	152.45 (12)	C36—C37—C38—N31	178.4 (2)
O2W—Na—N12—O12	−109.79 (13)	C34—C33—C38—C37	0.2 (3)
O1W—Na—N12—O12	54.69 (13)	C32—C33—C38—C37	−179.93 (18)
O1Wⁱ—Na—N12—O12	−23.17 (13)	C34—C33—C38—N31	−178.94 (17)
O11—Na—N12—O12	177.94 (13)	C32—C33—C38—N31	0.9 (2)
Naⁱ—Na—N12—O12	15.78 (13)	O21—C21—N21—C28	−177.48 (16)
Naⁱⁱ—Na—N12—O12	168.41 (11)	C22—C21—N21—C28	1.97 (18)
N11—C11—O11—Naⁱⁱ	−24.6 (4)	C27—C28—N21—C21	178.38 (17)
C12—C11—O11—Naⁱⁱ	154.56 (15)	C23—C28—N21—C21	−0.82 (19)
N11—C11—O11—Na	177.89 (15)	C23—C22—N22—O22	−2.8 (3)
C12—C11—O11—Na	−2.9 (2)	C21—C22—N22—O22	179.10 (13)
O11ⁱⁱ—Na—O11—C11	166.41 (17)	O31—C31—N31—C38	177.8 (2)
O2W—Na—O11—C11	−102.83 (15)	C32—C31—N31—C38	−2.1 (2)
O1W—Na—O11—C11	77.18 (16)	C37—C38—N31—C31	−178.2 (2)
O1Wⁱ—Na—O11—C11	−71.9 (2)	C33—C38—N31—C31	0.8 (2)
N12—Na—O11—C11	2.38 (13)	C33—C32—N32—O32	2.5 (3)
Naⁱ—Na—O11—C11	57.8 (2)	C31—C32—N32—O32	−179.19 (15)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O21ⁱⁱⁱ	0.87 (2)	1.97 (2)	2.846 (5)	175 (2)
O22—H22···O12	0.94 (2)	1.70 (2)	2.633 (3)	171 (2)
O22—H22···N12	0.94 (2)	2.45 (2)	3.226 (4)	140 (2)

Symmetry code: (iii) −x−1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Na(C₈H₅N₂O₂)(H₂O)₂]·2C₈H₆N₂O₂
M_r	544.45
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.2987 (3), 11.9269 (5), 15.0756 (6)
α, β, γ (°)	95.369 (2), 102.871 (2), 102.631 (2)
V (Å³)	1234.36 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.74 × 0.23 × 0.18

Data collection
Diffractometer	Bruker CCD X8 APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.912, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	25159, 7175, 4225
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.135, 1.04
No. of reflections	7175
No. of parameters	388
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.35

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O21ⁱ	0.87 (2)	1.97 (2)	2.846 (5)	175 (2)
O22—H22···O12	0.94 (2)	1.70 (2)	2.633 (3)	171 (2)
O22—H22···N12	0.94 (2)	2.45 (2)	3.226 (4)	140 (2)

Symmetry code: (i) −x−1, −y, −z.

Acknowledgements

We gratefully acknowledge financial support by the CNPq and FAPERGS.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2003). SMART, SAINT, SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chafeev, M., Chakka, N., Chowdhury, S., Fraser, R., Fu, J., Hou, D., Hsieh, T., Kamboj, R., Liu, S., Raina, V., Seid Bagherzadeh, M., Sun, J., Sun, S. & Viridov, S. (2008). International Patent Cooperation Treaty. WO2008046083A2. Google Scholar
Hudák, A. & Košturiak, A. (1999). J. Therm. Anal. Cal. 58, 579–587. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m790-m791

doi:10.1107/S1600536811018290

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

A one-dimensional coordination polymer constructed from isatine-3-oximate and sodium

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds