catena-Poly[[bis­(μ-2-formyl-6-meth­oxy­phenolato)copper(II)sodium]-μ-nitrato]

Gao, P.; Hou, H.-G.; Gao, T.; Yang, J.-L.; Yang, Y.

doi:10.1107/S1600536811040025

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1522

doi:10.1107/S1600536811040025

Open

access

catena-Poly[[bis(μ-2-formyl-6-methoxyphenolato)copper(II)sodium]-μ-nitrato]

Po Gao,^a Hai-Ge Hou,^a Ting Gao,^a ^* Jing-Lin Yang ^a and Yu Yang ^a

^aSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: gaoting1218@yahoo.com.cn

(Received 24 September 2011; accepted 29 September 2011; online 12 October 2011)

In the title heterodinuclear complex, [CuNa(C₈H₇O₃)₂(NO₃)]_n, the Cu^II ion is five-coordinated in a square-pyramidal arrangement by four atoms of two different ligand molecules in equatorial positions and one remote nitrate O atom in the apical position. The Na⁺ ion is eight-coordinated by four ligand O atoms and four nitrate O atoms. The ligand links the Cu^II and Na ions, forming a layered arrangement extending parallel to (001).

Related literature

For similar nickel–sodium complexes, see Costes et al. (1997a ,b ).

Experimental

Crystal data

[CuNa(C₈H₇O₃)₂(NO₃)]
M_r = 450.81
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.737 (2) Å
b = 13.165 (4) Å
c = 16.889 (6) Å
V = 1720.2 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.35 mm⁻¹
T = 293 K
0.35 × 0.33 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.648, T_max = 0.691
16868 measured reflections
3926 independent reflections
3692 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.057
S = 1.03
3926 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1671 Friedel pairs
Flack parameter: 0.007 (8)

Table 1
Selected bond lengths (Å)

Cu1—O5	1.8989 (12)
Cu1—O2	1.9074 (12)
Cu1—O6	1.9487 (12)
Cu1—O3	1.9608 (14)
Cu1—O7	2.3560 (14)
Na1—O2	2.3667 (16)
Na1—O5	2.3900 (14)
Na1—O8ⁱ	2.4154 (17)
Na1—O1	2.5249 (15)
Na1—O4	2.6129 (16)
Na1—O9ⁱ	2.749 (2)
Na1—O9ⁱⁱ	2.755 (2)
Na1—O8	2.937 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) x-1, y, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 .

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811040025/ng5236sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040025/ng5236Isup2.hkl

checkCIF report

Comment top

Orthovanillin is a commercial ligand that is able to chelate 3 d ions,mainly with copper ions. Furthermore, orthovanillin can also yield heterodinuclear 3 d-4f complexes and the first examples involve Cu—Ln complexes (Costes et al., 1997a,b). We were interested in the nature of the products obtained by reacting a mononuclear 3 d complex with alkali metal ions. As shown in Fig. 1, The Cu^II is four-coordinated by two aldehyde oxygen atoms and two phenol oxygen atoms from the two orthovanillin ligands. The copper atom centre is inserted into the inner cavity. The Na ion is ligated by two hydroxyl oxygen atoms, two methoxyl oxygen atoms, two oxygen atoms of one bidentate nitrate counterion and two oxygen atoms of two different monodentate nitrate counterion. The Cu^II and Na are bridged by the phenolic oxygen atoms, layered arrangement extending parallel to (001).

Related literature top

For similar nickel–sodium complexes, see Costes et al. (1997a,b).

Experimental top

To a solution of o-vanillin (0.046 g, 0.20 mmol) in dichloromethane (5 ml) was added to a solution of copper(II) acetate monohydrate (0.040 g, 0.20 mmol) and sodium nitrate (0.086 g, 0.20 mmol) in ethanol (5 ml). The mixture was stirred, heated under reflux (30 min) and then allowed to cool to room temperature. Yield: 70%. The crystals suitable for X-ray determination were obtained by slow diffusion of diethylether into the solution for one week. Analysis calculated for C₁₆H₁₄NCuNaO₉: C 42.63, H 3.13, N 3.11%; Found: C 42.29, H 3.17, N, 3.22%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008.

Figures top

Fig. 1. The molecular structure of the the title compound, showing 30% probability displacement ellipsoids.

catena-Poly[[bis(µ-2-formyl-6-methoxyphenolato)copper(II)sodium]- µ-nitrato] top

Crystal data top

[CuNa(C₈H₇O₃)₂(NO₃)]	F(000) = 916
M_r = 450.81	D_x = 1.741 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 15663 reflections
a = 7.737 (2) Å	θ = 3.1–27.5°
b = 13.165 (4) Å	µ = 1.35 mm⁻¹
c = 16.889 (6) Å	T = 293 K
V = 1720.2 (9) Å³	Block, brown
Z = 4	0.35 × 0.33 × 0.30 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3926 independent reflections
Radiation source: fine-focus sealed tube	3692 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→10
T_min = 0.648, T_max = 0.691	k = −17→16
16868 measured reflections	l = −21→21

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)] = 0.021	H-atom parameters constrained
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0375P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3926 reflections	Δρ_max = 0.22 e Å⁻³
255 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1671 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.007 (8)

Crystal data top

[CuNa(C₈H₇O₃)₂(NO₃)]	V = 1720.2 (9) Å³
M_r = 450.81	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.737 (2) Å	µ = 1.35 mm⁻¹
b = 13.165 (4) Å	T = 293 K
c = 16.889 (6) Å	0.35 × 0.33 × 0.30 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3926 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3692 reflections with I > 2σ(I)
T_min = 0.648, T_max = 0.691	R_int = 0.025
16868 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.057	Δρ_max = 0.22 e Å⁻³
S = 1.03	Δρ_min = −0.21 e Å⁻³
3926 reflections	Absolute structure: Flack (1983), 1671 Friedel pairs
255 parameters	Absolute structure parameter: 0.007 (8)
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	0.0679 (2)	0.92359 (12)	0.67688 (10)	0.0321 (3)
C2	0.0859 (2)	1.02319 (13)	0.70061 (11)	0.0375 (4)
H2	0.0378	1.0749	0.6703	0.045*
C3	0.1765 (2)	1.04734 (13)	0.77039 (12)	0.0411 (4)
H3	0.1895	1.1148	0.7856	0.049*
C4	0.2450 (3)	0.97166 (13)	0.81555 (10)	0.0406 (4)
H4	0.3025	0.9878	0.8622	0.049*
C5	0.2298 (2)	0.86831 (12)	0.79230 (10)	0.0331 (3)
C6	0.14000 (19)	0.84231 (11)	0.72185 (10)	0.0293 (3)
C7	0.3021 (2)	0.79245 (15)	0.84132 (11)	0.0401 (4)
H7	0.3452	0.8149	0.8897	0.048*
C8	−0.0953 (3)	0.96653 (15)	0.56154 (13)	0.0484 (5)
H8A	−0.1781	1.0034	0.5926	0.073*
H8B	−0.1529	0.9341	0.5180	0.073*
H8C	−0.0095	1.0126	0.5416	0.073*
C9	0.0758 (2)	0.44760 (12)	0.54819 (9)	0.0309 (3)
C10	0.0625 (3)	0.34687 (13)	0.52792 (12)	0.0421 (4)
H10	0.0032	0.3281	0.4823	0.051*
C11	0.1387 (3)	0.27166 (13)	0.57635 (13)	0.0495 (5)
H11	0.1292	0.2036	0.5622	0.059*
C12	0.2248 (3)	0.29714 (13)	0.64274 (12)	0.0446 (5)
H12	0.2738	0.2466	0.6740	0.054*
C13	0.2416 (3)	0.40139 (11)	0.66559 (10)	0.0337 (3)
C14	0.1682 (2)	0.47851 (12)	0.61750 (9)	0.0287 (3)
C15	0.3276 (2)	0.42379 (13)	0.73717 (11)	0.0379 (4)
H15	0.3728	0.3688	0.7648	0.046*
C16	−0.0964 (3)	0.50378 (17)	0.43943 (13)	0.0513 (5)
H16A	−0.0241	0.4728	0.4000	0.077*
H16B	−0.1458	0.5650	0.4185	0.077*
H16C	−0.1872	0.4577	0.4538	0.077*
Cu1	0.25742 (3)	0.636953 (13)	0.726538 (11)	0.03049 (6)
N1	0.5362 (2)	0.72115 (11)	0.60308 (10)	0.0391 (3)
Na1	0.03464 (14)	0.71081 (6)	0.56511 (5)	0.0556 (2)
O1	−0.01427 (18)	0.89168 (9)	0.60950 (8)	0.0423 (3)
O2	0.11760 (15)	0.74989 (9)	0.69651 (7)	0.0349 (3)
O3	0.31612 (18)	0.69909 (10)	0.82857 (8)	0.0433 (3)
O4	0.00468 (16)	0.52733 (9)	0.50775 (7)	0.0367 (3)
O5	0.17851 (16)	0.57479 (8)	0.63174 (7)	0.0330 (2)
O6	0.34982 (16)	0.50983 (9)	0.76779 (8)	0.0386 (3)
O7	0.51745 (17)	0.70304 (11)	0.67537 (8)	0.0449 (3)
O8	0.4100 (2)	0.74389 (12)	0.56117 (8)	0.0547 (4)
O9	0.6790 (2)	0.7162 (2)	0.57232 (13)	0.0937 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0297 (8)	0.0350 (8)	0.0315 (8)	0.0009 (7)	0.0035 (7)	−0.0002 (7)
C2	0.0381 (9)	0.0324 (8)	0.0421 (10)	0.0028 (7)	0.0080 (7)	0.0033 (7)
C3	0.0414 (9)	0.0336 (8)	0.0482 (10)	−0.0039 (7)	0.0074 (9)	−0.0076 (8)
C4	0.0388 (9)	0.0458 (9)	0.0373 (8)	−0.0037 (10)	0.0026 (9)	−0.0099 (7)
C5	0.0318 (8)	0.0379 (8)	0.0296 (7)	0.0008 (8)	0.0032 (6)	−0.0020 (6)
C6	0.0266 (7)	0.0320 (7)	0.0294 (7)	0.0012 (6)	0.0037 (6)	−0.0007 (6)
C7	0.0437 (10)	0.0507 (9)	0.0258 (8)	0.0024 (8)	−0.0044 (7)	−0.0043 (7)
C8	0.0524 (12)	0.0468 (10)	0.0461 (11)	0.0120 (10)	−0.0117 (9)	0.0078 (9)
C9	0.0315 (8)	0.0313 (7)	0.0299 (8)	0.0006 (7)	0.0048 (7)	0.0017 (6)
C10	0.0514 (10)	0.0351 (8)	0.0399 (9)	−0.0018 (8)	0.0041 (8)	−0.0086 (8)
C11	0.0703 (14)	0.0269 (7)	0.0513 (12)	0.0020 (9)	0.0068 (11)	−0.0041 (8)
C12	0.0541 (12)	0.0288 (7)	0.0508 (10)	0.0105 (9)	0.0092 (10)	0.0069 (7)
C13	0.0352 (8)	0.0291 (6)	0.0367 (8)	0.0024 (8)	0.0045 (8)	0.0056 (6)
C14	0.0289 (7)	0.0278 (7)	0.0293 (8)	0.0006 (6)	0.0053 (6)	0.0029 (6)
C15	0.0399 (9)	0.0345 (8)	0.0394 (10)	0.0085 (8)	0.0024 (8)	0.0116 (7)
C16	0.0540 (12)	0.0548 (11)	0.0453 (11)	−0.0040 (10)	−0.0180 (10)	−0.0021 (9)
Cu1	0.03520 (10)	0.02981 (9)	0.02645 (10)	0.00292 (9)	−0.00451 (9)	0.00259 (7)
N1	0.0461 (9)	0.0354 (7)	0.0357 (8)	−0.0090 (7)	0.0044 (7)	0.0047 (6)
Na1	0.0954 (7)	0.0374 (4)	0.0340 (4)	0.0132 (4)	−0.0188 (4)	0.0012 (3)
O1	0.0518 (7)	0.0344 (6)	0.0407 (7)	0.0082 (6)	−0.0130 (6)	0.0016 (5)
O2	0.0404 (6)	0.0302 (5)	0.0340 (6)	0.0051 (5)	−0.0081 (5)	−0.0019 (5)
O3	0.0581 (8)	0.0437 (6)	0.0282 (6)	0.0092 (6)	−0.0082 (6)	0.0006 (5)
O4	0.0423 (7)	0.0344 (6)	0.0334 (6)	0.0006 (6)	−0.0082 (5)	0.0009 (5)
O5	0.0434 (6)	0.0244 (5)	0.0312 (6)	−0.0007 (5)	−0.0066 (5)	0.0042 (4)
O6	0.0415 (6)	0.0402 (6)	0.0343 (6)	0.0054 (5)	−0.0075 (6)	0.0078 (5)
O7	0.0448 (7)	0.0593 (8)	0.0305 (6)	−0.0087 (6)	−0.0033 (6)	0.0084 (6)
O8	0.0627 (9)	0.0642 (9)	0.0373 (8)	−0.0019 (8)	−0.0063 (7)	0.0162 (7)
O9	0.0520 (10)	0.158 (2)	0.0716 (13)	−0.0040 (12)	0.0224 (9)	0.0250 (14)

Geometric parameters (Å, º) top

C1—O1	1.370 (2)	C14—O5	1.2925 (19)
C1—C2	1.378 (2)	C15—O6	1.257 (2)
C1—C6	1.426 (2)	C15—H15	0.9300
C2—C3	1.407 (3)	C16—O4	1.428 (2)
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.362 (3)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.421 (2)	Cu1—O5	1.8989 (12)
C4—H4	0.9300	Cu1—O2	1.9074 (12)
C5—C7	1.413 (2)	Cu1—O6	1.9487 (12)
C5—C6	1.420 (2)	Cu1—O3	1.9608 (14)
C6—O2	1.3013 (19)	Cu1—O7	2.3560 (14)
C7—O3	1.252 (2)	Cu1—Na1	3.3688 (11)
C7—H7	0.9300	N1—O9	1.223 (2)
C8—O1	1.421 (2)	N1—O8	1.243 (2)
C8—H8A	0.9600	N1—O7	1.252 (2)
C8—H8B	0.9600	N1—Na1ⁱ	2.978 (2)
C8—H8C	0.9600	Na1—O2	2.3667 (16)
C9—O4	1.368 (2)	Na1—O5	2.3900 (14)
C9—C10	1.373 (2)	Na1—O8ⁱⁱ	2.4154 (17)
C9—C14	1.431 (2)	Na1—O1	2.5249 (15)
C10—C11	1.413 (3)	Na1—O4	2.6129 (16)
C10—H10	0.9300	Na1—O9ⁱⁱ	2.749 (2)
C11—C12	1.347 (3)	Na1—O9ⁱⁱⁱ	2.755 (2)
C11—H11	0.9300	Na1—O8	2.937 (2)
C12—C13	1.431 (2)	Na1—N1ⁱⁱ	2.978 (2)
C12—H12	0.9300	O8—Na1ⁱ	2.4154 (17)
C13—C15	1.411 (3)	O9—Na1ⁱ	2.749 (2)
C13—C14	1.419 (2)	O9—Na1^iv	2.755 (2)

O1—C1—C2	125.48 (15)	O8—N1—O7	120.68 (16)
O1—C1—C6	113.20 (14)	O9—N1—Na1ⁱ	67.31 (13)
C2—C1—C6	121.31 (16)	O8—N1—Na1ⁱ	51.77 (9)
C1—C2—C3	120.59 (16)	O7—N1—Na1ⁱ	170.58 (13)
C1—C2—H2	119.7	O2—Na1—O5	66.12 (4)
C3—C2—H2	119.7	O2—Na1—O8ⁱⁱ	151.95 (6)
C4—C3—C2	119.82 (16)	O5—Na1—O8ⁱⁱ	141.87 (6)
C4—C3—H3	120.1	O2—Na1—O1	63.72 (4)
C2—C3—H3	120.1	O5—Na1—O1	129.54 (5)
C3—C4—C5	120.89 (17)	O8ⁱⁱ—Na1—O1	88.25 (6)
C3—C4—H4	119.6	O2—Na1—O4	124.94 (5)
C5—C4—H4	119.6	O5—Na1—O4	61.52 (4)
C7—C5—C6	120.96 (15)	O8ⁱⁱ—Na1—O4	82.27 (5)
C7—C5—C4	118.82 (16)	O1—Na1—O4	165.61 (6)
C6—C5—C4	120.21 (15)	O2—Na1—O9ⁱⁱ	127.27 (7)
O2—C6—C5	124.49 (14)	O5—Na1—O9ⁱⁱ	118.04 (7)
O2—C6—C1	118.32 (15)	O8ⁱⁱ—Na1—O9ⁱⁱ	47.97 (5)
C5—C6—C1	117.18 (14)	O1—Na1—O9ⁱⁱ	88.98 (7)
O3—C7—C5	128.84 (17)	O4—Na1—O9ⁱⁱ	92.63 (7)
O3—C7—H7	115.6	O2—Na1—O9ⁱⁱⁱ	102.93 (7)
C5—C7—H7	115.6	O5—Na1—O9ⁱⁱⁱ	117.63 (7)
O1—C8—H8A	109.5	O8ⁱⁱ—Na1—O9ⁱⁱⁱ	68.52 (6)
O1—C8—H8B	109.5	O1—Na1—O9ⁱⁱⁱ	79.21 (7)
H8A—C8—H8B	109.5	O4—Na1—O9ⁱⁱⁱ	87.24 (7)
O1—C8—H8C	109.5	O9ⁱⁱ—Na1—O9ⁱⁱⁱ	115.72 (6)
H8A—C8—H8C	109.5	O2—Na1—O8	73.79 (5)
H8B—C8—H8C	109.5	O5—Na1—O8	70.20 (5)
O4—C9—C10	125.88 (16)	O8ⁱⁱ—Na1—O8	109.77 (5)
O4—C9—C14	113.03 (14)	O1—Na1—O8	90.86 (5)
C10—C9—C14	121.08 (16)	O4—Na1—O8	102.50 (6)
C9—C10—C11	120.06 (18)	O9ⁱⁱ—Na1—O8	61.80 (5)
C9—C10—H10	120.0	O9ⁱⁱⁱ—Na1—O8	169.91 (7)
C11—C10—H10	120.0	O2—Na1—N1ⁱⁱ	145.87 (6)
C12—C11—C10	120.92 (16)	O5—Na1—N1ⁱⁱ	132.26 (6)
C12—C11—H11	119.5	O8ⁱⁱ—Na1—N1ⁱⁱ	23.83 (5)
C10—C11—H11	119.5	O1—Na1—N1ⁱⁱ	90.01 (5)
C11—C12—C13	120.54 (17)	O4—Na1—N1ⁱⁱ	85.69 (5)
C11—C12—H12	119.7	O9ⁱⁱ—Na1—N1ⁱⁱ	24.23 (5)
C13—C12—H12	119.7	O9ⁱⁱⁱ—Na1—N1ⁱⁱ	92.20 (6)
C15—C13—C14	121.97 (15)	O8—Na1—N1ⁱⁱ	85.98 (5)
C15—C13—C12	118.31 (16)	O2—Na1—Cu1	33.40 (3)
C14—C13—C12	119.70 (16)	O5—Na1—Cu1	33.32 (3)
O5—C14—C13	124.79 (15)	O8ⁱⁱ—Na1—Cu1	171.94 (5)
O5—C14—C9	117.52 (14)	O1—Na1—Cu1	96.23 (4)
C13—C14—C9	117.69 (15)	O4—Na1—Cu1	94.51 (4)
O6—C15—C13	127.26 (15)	O9ⁱⁱ—Na1—Cu1	125.19 (5)
O6—C15—H15	116.4	O9ⁱⁱⁱ—Na1—Cu1	118.86 (6)
C13—C15—H15	116.4	O8—Na1—Cu1	63.60 (3)
O4—C16—H16A	109.5	N1ⁱⁱ—Na1—Cu1	148.94 (5)
O4—C16—H16B	109.5	C1—O1—C8	117.75 (14)
H16A—C16—H16B	109.5	C1—O1—Na1	117.80 (10)
O4—C16—H16C	109.5	C8—O1—Na1	123.41 (12)
H16A—C16—H16C	109.5	C6—O2—Cu1	124.46 (10)
H16B—C16—H16C	109.5	C6—O2—Na1	123.21 (11)
O5—Cu1—O2	85.95 (5)	Cu1—O2—Na1	103.51 (5)
O5—Cu1—O6	92.82 (5)	C7—O3—Cu1	122.72 (12)
O2—Cu1—O6	166.56 (5)	C9—O4—C16	117.21 (14)
O5—Cu1—O3	174.40 (6)	C9—O4—Na1	119.25 (10)
O2—Cu1—O3	92.28 (5)	C16—O4—Na1	123.29 (11)
O6—Cu1—O3	87.66 (6)	C14—O5—Cu1	126.82 (10)
O5—Cu1—O7	97.15 (5)	C14—O5—Na1	128.20 (11)
O2—Cu1—O7	95.67 (5)	Cu1—O5—Na1	102.93 (5)
O6—Cu1—O7	97.76 (5)	C15—O6—Cu1	125.21 (11)
O3—Cu1—O7	88.31 (6)	N1—O7—Cu1	121.78 (11)
O5—Cu1—Na1	43.75 (4)	N1—O8—Na1ⁱ	104.40 (12)
O2—Cu1—Na1	43.08 (4)	N1—O8—Na1	136.74 (11)
O6—Cu1—Na1	136.46 (4)	Na1ⁱ—O8—Na1	116.83 (6)
O3—Cu1—Na1	135.18 (4)	N1—O9—Na1ⁱ	88.46 (14)
O7—Cu1—Na1	91.92 (4)	N1—O9—Na1^iv	157.32 (17)
O9—N1—O8	118.74 (18)	Na1ⁱ—O9—Na1^iv	112.18 (7)
O9—N1—O7	120.58 (18)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1/2, −y+3/2, −z+1; (iii) x−1, y, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[CuNa(C₈H₇O₃)₂(NO₃)]
M_r	450.81
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	7.737 (2), 13.165 (4), 16.889 (6)
V (Å³)	1720.2 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.35
Crystal size (mm)	0.35 × 0.33 × 0.30

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.648, 0.691
No. of measured, independent and observed [I > 2σ(I)] reflections	16868, 3926, 3692
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.057, 1.03
No. of reflections	3926
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21
Absolute structure	Flack (1983), 1671 Friedel pairs
Absolute structure parameter	0.007 (8)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008.

Selected bond lengths (Å) top

Cu1—O5	1.8989 (12)	Na1—O8ⁱ	2.4154 (17)
Cu1—O2	1.9074 (12)	Na1—O1	2.5249 (15)
Cu1—O6	1.9487 (12)	Na1—O4	2.6129 (16)
Cu1—O3	1.9608 (14)	Na1—O9ⁱ	2.749 (2)
Cu1—O7	2.3560 (14)	Na1—O9ⁱⁱ	2.755 (2)
Na1—O2	2.3667 (16)	Na1—O8	2.937 (2)
Na1—O5	2.3900 (14)

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x−1, y, z.

Acknowledgements

The authors gratefully acknowledge financial support from Heilongjiang Province (12511386) and Key Laboratory of Chemical Engineering Processes & Technology for High-efficiency Conversion, College of Heilongjiang Province.

References

Costes, J. P., Dahan, F., Dupuis, A. & Laurent, J. P. (1997a). Inorg. Chem. 36, 3429–3433. CSD CrossRef PubMed CAS Web of Science Google Scholar
Costes, J. P., Laurent, J. P., Chabert, P., Commenges, G. & Dahan, F. (1997b). Inorg. Chem. 36, 656–660. CSD CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef 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.