Tetra­kis[μ3-4-nitro-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamidato]tetra­kis­[methano­lsodium(I)]

Yin, G.-J.; Zhang, Q.; Li, D.

doi:10.1107/S1600536812014791

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m570

doi:10.1107/S1600536812014791

Open

access

Tetrakis[μ₃-4-nitro-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamidato]tetrakis[methanolsodium(I)]

Guo-Jie Yin,^a ^* Qing Zhang ^a and Dong Li ^a

^aDepartment of Environment Engineering and Chemistry, Luoyang Institute of Science and Technology, 471023 Luoyang, People's Republic of China
^*Correspondence e-mail: yinguojie000000@yahoo.com.cn

(Received 19 March 2012; accepted 4 April 2012; online 13 April 2012)

In the title compound, [Na₄(C₁₅H₉N₄O₄)₄(CH₃OH)₄], the N₃O₃ environment around the Na⁺ ion is distorted octahedral. In the unit cell, four Na⁺ ions are bridged by four Schiff base anions, leading to a tetranuclear complex with -4 symmetry. O—H⋯N hydrogen bonds between the methanol molecule and the Schiff base anion stabilize the structural set-up.

Related literature

For the preparation of 2-amino-5-phenyl-1,3,4-oxadiazole, see: Gibson (1962 ) and of N-(5-phenyl-1,3,4-oxadiazol-2-yl)-p-nitrobenzamide, see: Zhang et al. (2009 ). Organic ligands based on oxadiazole or carboxylate groups have both good coordination ability and diverse coordination modes, see: Hu et al. (2008 ).

Experimental

Crystal data

[Na₄(C₁₅H₉N₄O₄)₄(CH₄O)₄]
M_r = 1457.18
Tetragonal, I 4₁ /a
a = 15.6635 (2) Å
c = 27.1833 (6) Å
V = 6669.29 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.934, T_max = 1.000
15582 measured reflections
3413 independent reflections
2653 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.106
S = 1.02
3413 reflections
239 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected bond lengths (Å)

Na1—O5	2.3413 (14)
Na1—N1	2.3828 (15)
Na1—O1	2.3848 (13)
Na1—O1ⁱ	2.3972 (13)
Na1—N2ⁱⁱ	2.4127 (15)
Na1—N1ⁱⁱ	2.9859 (15)
Symmetry codes: (i) $[y+{\script{3\over 4}}, -x+{\script{5\over 4}}, -z+{\script{1\over 4}}]$ ; (ii) $[-y+{\script{5\over 4}}, x-{\script{3\over 4}}, -z+{\script{1\over 4}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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/S1600536812014791/hp2035sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014791/hp2035Isup2.hkl

checkCIF report

Comment top

As we all know, the organic ligands based on oxadiazole or carboxylate groups which containing N and O donors have both good coordination ability and diverse coordination modes (Hu et al., 2008). Therefore, the ligand N-(5-phenyl-1,3,4-oxadiazol-2-yl)- p-nitrobenzamide was chosen to create coordination architectures.

In the title compound, each Na^I atom is six-coordinated by one O atom from a methyl alcohol, two O atoms and three N atoms from the ligands, forming a distorted octahedral geometry. In the asymmetric unit, the four Na^I ions are bridged by four Schiff base anions, leading to a tetranuclear complex (Fig. 1 and Fig. 2), the coordination geometry of sodium ions can be described as distorted quadrilateral.

Related literature top

For the preparation of 2-amino-5-phenyl-1,3,4-oxadiazole, see: Gibson (1962) and of N-(5-phenyl-1,3,4-oxadiazol-2-yl)-p-nitrobenzamide, see: Zhang et al. (2009). Organic ligands based on oxadiazole or carboxylate groups have both good coordination ability and diverse coordination modes, see: Hu et al. (2008).

Experimental top

Reagents and solvents were of commercially available quality. The preparation of 2-Amino-5-phenyl-1,3,4-oxadiazole is based on a published method (Gibson, 1962). Bromine (0.66 ml) in glacial acetic acid (1.34 ml) was added to a stirred slurry of benzaldehyde semicarbazone (2.0 g) and powdered, anhydrous sodium acetate (4.0 g) in acetic acid (12 ml). The solids were dissolved giving a red solution, which suddenly grew warm and rapidly faded with white precipitate formed (sodium bromide). After 15 minutes, the mixture was poured into water (100 ml), and the precipitated solid (1.8 g) collected, washed and dried. Crystallization from ethanol gave stout needles.

The ligand of N-(5-phenyl-1,3,4-oxadiazol-2-yl)-p-nitrobenzamide was synthesized according to the method of literature (Zhang et al., 2009). 4-Nitrobenzoyl chloride (5.94 g, 0.032 mol) was dropped slowly into the stirred slurry of 2-Amino-5-phenyl-1,3,4-oxadiazole (5.64 g, 0.035 mol) in 50 ml pyridine. 2-Amino-5-phenyl-1,3,4-oxadiazole dissolved gradually and gave a buff solution. After 2 h, the solution was poured into water. Then the sodium hydroxide (2.80 g, 0.07 mol) was added to give a alkaline solution, the precipitate was collected and dried under vacuum. The title compound was obtained by re-crystallization from ethanol. Yield: 5.7 g, 60%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (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 title complex with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The molecular structure of the title complex with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

Tetrakis[µ₃-4-nitro-N-(5-phenyl-1,3,4-oxadiazol-2- yl)benzamidato]tetrakis[methanolsodium(I)] top

Crystal data top

[Na₄(C₁₅H₉N₄O₄)₄(CH₄O)₄]	D_x = 1.451 Mg m⁻³
M_r = 1457.18	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 5181 reflections
a = 15.6635 (2) Å	θ = 3.0–29.0°
c = 27.1833 (6) Å	µ = 0.13 mm⁻¹
V = 6669.29 (18) Å³	T = 293 K
Z = 4	Prismatic, yellow
F(000) = 3008	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3413 independent reflections
Radiation source: fine-focus sealed tube	2653 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −17→19
T_min = 0.934, T_max = 1.000	k = −19→19
15582 measured reflections	l = −33→30

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0488P)² + 3.8193P] where P = (F_o² + 2F_c²)/3
3413 reflections	(Δ/σ)_max < 0.001
239 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Na₄(C₁₅H₉N₄O₄)₄(CH₄O)₄]	Z = 4
M_r = 1457.18	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.13 mm⁻¹
a = 15.6635 (2) Å	T = 293 K
c = 27.1833 (6) Å	0.30 × 0.20 × 0.20 mm
V = 6669.29 (18) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3413 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2653 reflections with I > 2σ(I)
T_min = 0.934, T_max = 1.000	R_int = 0.027
15582 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	2 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.22 e Å⁻³
3413 reflections	Δρ_min = −0.22 e Å⁻³
239 parameters

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
Na1	0.83748 (4)	0.26324 (4)	0.11911 (2)	0.03798 (19)
O1	0.85910 (8)	0.13991 (7)	0.16902 (4)	0.0404 (3)
O2	0.90153 (7)	0.31903 (7)	0.27519 (4)	0.0363 (3)
O3	0.65522 (12)	−0.23034 (10)	0.22897 (7)	0.0783 (5)
O4	0.63373 (12)	−0.18639 (10)	0.30241 (6)	0.0805 (5)
O5	0.69874 (9)	0.29271 (10)	0.14628 (5)	0.0532 (4)
H5	0.6938 (13)	0.2932 (16)	0.1773 (3)	0.080*
N1	0.90347 (9)	0.30288 (9)	0.19472 (5)	0.0386 (3)
N2	0.93939 (9)	0.38225 (9)	0.20680 (5)	0.0388 (3)
N3	0.84467 (9)	0.19219 (8)	0.24835 (5)	0.0352 (3)
C1	1.00589 (13)	0.52826 (12)	0.26187 (9)	0.0571 (5)
H1	1.0161	0.5274	0.2282	0.069*
C2	1.03166 (15)	0.59702 (14)	0.28927 (12)	0.0733 (7)
H2	1.0593	0.6426	0.2742	0.088*
C3	1.01644 (15)	0.59842 (15)	0.33943 (12)	0.0743 (8)
H3	1.0341	0.6448	0.3582	0.089*
C4	0.97544 (15)	0.53153 (15)	0.36130 (9)	0.0660 (6)
H4	0.9649	0.5329	0.3950	0.079*
C5	0.94954 (13)	0.46210 (12)	0.33403 (7)	0.0488 (5)
H5A	0.9219	0.4167	0.3492	0.059*
C6	0.96483 (10)	0.46020 (10)	0.28401 (7)	0.0373 (4)
C7	0.93688 (10)	0.38873 (10)	0.25373 (6)	0.0330 (4)
C8	0.88199 (10)	0.26667 (10)	0.23605 (6)	0.0324 (4)
C9	0.83531 (10)	0.13374 (10)	0.21273 (6)	0.0322 (4)
C10	0.79134 (10)	0.05235 (10)	0.22781 (6)	0.0332 (4)
C11	0.76375 (13)	0.03611 (11)	0.27529 (7)	0.0468 (5)
H11	0.7734	0.0763	0.2998	0.056*
C12	0.72214 (13)	−0.03911 (12)	0.28662 (7)	0.0504 (5)
H12	0.7033	−0.0496	0.3185	0.060*
C13	0.70909 (11)	−0.09794 (10)	0.25015 (7)	0.0409 (4)
C14	0.73597 (13)	−0.08450 (12)	0.20282 (7)	0.0503 (5)
H14	0.7268	−0.1254	0.1786	0.060*
C15	0.77700 (12)	−0.00895 (12)	0.19195 (7)	0.0460 (4)
H15	0.7954	0.0011	0.1599	0.055*
N4	0.66286 (11)	−0.17717 (10)	0.26138 (7)	0.0527 (4)
C16	0.61860 (15)	0.30244 (17)	0.12369 (9)	0.0732 (7)
H16A	0.6260	0.3257	0.0913	0.110*
H16B	0.5840	0.3404	0.1429	0.110*
H16C	0.5911	0.2478	0.1214	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0474 (4)	0.0400 (4)	0.0266 (3)	0.0005 (3)	0.0019 (3)	−0.0022 (3)
O1	0.0541 (8)	0.0366 (6)	0.0305 (6)	−0.0014 (5)	0.0096 (5)	−0.0032 (5)
O2	0.0489 (7)	0.0342 (6)	0.0257 (6)	−0.0075 (5)	0.0036 (5)	−0.0010 (5)
O3	0.0961 (13)	0.0499 (9)	0.0890 (12)	−0.0320 (8)	0.0193 (10)	−0.0198 (9)
O4	0.1073 (14)	0.0652 (10)	0.0691 (11)	−0.0349 (9)	0.0210 (10)	0.0069 (8)
O5	0.0461 (8)	0.0717 (9)	0.0420 (7)	−0.0027 (7)	0.0096 (6)	−0.0025 (7)
N1	0.0496 (9)	0.0373 (8)	0.0289 (7)	−0.0089 (7)	0.0050 (6)	−0.0008 (6)
N2	0.0448 (8)	0.0390 (8)	0.0327 (8)	−0.0083 (6)	0.0054 (6)	0.0014 (6)
N3	0.0436 (8)	0.0327 (7)	0.0293 (7)	−0.0048 (6)	0.0049 (6)	−0.0016 (6)
C1	0.0543 (12)	0.0471 (11)	0.0699 (14)	−0.0149 (9)	0.0119 (10)	−0.0055 (10)
C2	0.0597 (14)	0.0465 (13)	0.114 (2)	−0.0196 (10)	0.0090 (14)	−0.0121 (13)
C3	0.0555 (13)	0.0551 (14)	0.112 (2)	−0.0034 (11)	−0.0177 (14)	−0.0392 (14)
C4	0.0749 (16)	0.0620 (14)	0.0611 (14)	0.0022 (12)	−0.0168 (12)	−0.0249 (12)
C5	0.0574 (12)	0.0459 (11)	0.0431 (10)	0.0000 (9)	−0.0065 (9)	−0.0064 (9)
C6	0.0322 (9)	0.0350 (9)	0.0445 (10)	−0.0005 (7)	−0.0022 (7)	−0.0039 (8)
C7	0.0323 (8)	0.0330 (8)	0.0337 (9)	−0.0034 (7)	0.0030 (7)	0.0021 (7)
C8	0.0357 (8)	0.0348 (8)	0.0267 (8)	−0.0022 (7)	0.0034 (7)	−0.0036 (7)
C9	0.0332 (8)	0.0324 (8)	0.0310 (8)	0.0029 (7)	0.0020 (7)	−0.0014 (7)
C10	0.0333 (8)	0.0315 (8)	0.0347 (8)	0.0013 (7)	0.0013 (7)	−0.0026 (7)
C11	0.0656 (12)	0.0363 (9)	0.0384 (10)	−0.0087 (8)	0.0096 (9)	−0.0070 (8)
C12	0.0681 (13)	0.0432 (10)	0.0399 (10)	−0.0099 (9)	0.0136 (9)	0.0003 (8)
C13	0.0398 (9)	0.0330 (9)	0.0498 (10)	−0.0038 (7)	0.0046 (8)	0.0003 (8)
C14	0.0611 (12)	0.0421 (10)	0.0476 (11)	−0.0128 (9)	0.0047 (9)	−0.0114 (9)
C15	0.0571 (12)	0.0445 (10)	0.0365 (9)	−0.0103 (9)	0.0068 (8)	−0.0058 (8)
N4	0.0525 (10)	0.0408 (9)	0.0649 (12)	−0.0084 (7)	0.0070 (9)	0.0005 (9)
C16	0.0564 (14)	0.0979 (19)	0.0654 (15)	−0.0038 (12)	0.0021 (12)	0.0079 (14)

Geometric parameters (Å, º) top

Na1—O5	2.3413 (14)	C1—H1	0.9300
Na1—N1	2.3828 (15)	C2—C3	1.384 (4)
Na1—O1	2.3848 (13)	C2—H2	0.9300
Na1—O1ⁱ	2.3972 (13)	C3—C4	1.365 (4)
Na1—N2ⁱⁱ	2.4127 (15)	C3—H3	0.9300
Na1—N1ⁱⁱ	2.9859 (15)	C4—C5	1.377 (3)
Na1—Na1ⁱ	3.6261 (9)	C4—H4	0.9300
Na1—Na1ⁱⁱ	3.6261 (9)	C5—C6	1.381 (3)
O1—C9	1.2491 (19)	C5—H5A	0.9300
O1—Na1ⁱⁱ	2.3972 (13)	C6—C7	1.457 (2)
O2—C7	1.3559 (19)	C9—C10	1.506 (2)
O2—C8	1.3778 (18)	C10—C11	1.385 (2)
O3—N4	1.218 (2)	C10—C15	1.387 (2)
O4—N4	1.214 (2)	C11—C12	1.381 (3)
O5—C16	1.406 (3)	C11—H11	0.9300
O5—H5	0.847 (9)	C12—C13	1.369 (3)
N1—C8	1.303 (2)	C12—H12	0.9300
N1—N2	1.4036 (19)	C13—C14	1.370 (3)
N1—Na1ⁱ	2.9859 (15)	C13—N4	1.469 (2)
N2—C7	1.280 (2)	C14—C15	1.379 (3)
N2—Na1ⁱ	2.4127 (15)	C14—H14	0.9300
N3—C9	1.341 (2)	C15—H15	0.9300
N3—C8	1.347 (2)	C16—H16A	0.9600
C1—C2	1.370 (3)	C16—H16B	0.9600
C1—C6	1.383 (3)	C16—H16C	0.9600

O5—Na1—N1	94.54 (5)	C3—C2—H2	120.1
O5—Na1—O1	96.43 (5)	C4—C3—C2	119.8 (2)
N1—Na1—O1	70.05 (5)	C4—C3—H3	120.1
O5—Na1—O1ⁱ	106.86 (5)	C2—C3—H3	120.1
N1—Na1—O1ⁱ	90.40 (5)	C3—C4—C5	120.7 (2)
O1—Na1—O1ⁱ	150.81 (5)	C3—C4—H4	119.7
O5—Na1—N2ⁱⁱ	123.14 (5)	C5—C4—H4	119.7
N1—Na1—N2ⁱⁱ	141.02 (6)	C4—C5—C6	119.7 (2)
O1—Na1—N2ⁱⁱ	94.03 (5)	C4—C5—H5A	120.1
O1ⁱ—Na1—N2ⁱⁱ	87.87 (5)	C6—C5—H5A	120.1
O5—Na1—N1ⁱⁱ	146.17 (5)	C5—C6—C1	119.51 (17)
N1—Na1—N1ⁱⁱ	113.69 (6)	C5—C6—C7	121.38 (16)
O1—Na1—N1ⁱⁱ	77.43 (4)	C1—C6—C7	119.10 (17)
O1ⁱ—Na1—N1ⁱⁱ	91.84 (4)	N2—C7—O2	112.17 (14)
N2ⁱⁱ—Na1—N1ⁱⁱ	27.62 (4)	N2—C7—C6	127.92 (15)
O5—Na1—Na1ⁱ	123.35 (5)	O2—C7—C6	119.89 (14)
N1—Na1—Na1ⁱ	55.00 (4)	N1—C8—N3	134.68 (15)
O1—Na1—Na1ⁱ	111.36 (4)	N1—C8—O2	110.45 (13)
O1ⁱ—Na1—Na1ⁱ	40.56 (3)	N3—C8—O2	114.86 (13)
N2ⁱⁱ—Na1—Na1ⁱ	103.62 (4)	O1—C9—N3	126.97 (15)
N1ⁱⁱ—Na1—Na1ⁱ	89.20 (3)	O1—C9—C10	117.45 (14)
O5—Na1—Na1ⁱⁱ	136.08 (5)	N3—C9—C10	115.58 (14)
N1—Na1—Na1ⁱⁱ	80.91 (4)	C11—C10—C15	118.53 (16)
O1—Na1—Na1ⁱⁱ	40.82 (3)	C11—C10—C9	123.50 (15)
O1ⁱ—Na1—Na1ⁱⁱ	116.78 (3)	C15—C10—C9	117.97 (15)
N2ⁱⁱ—Na1—Na1ⁱⁱ	65.47 (4)	C12—C11—C10	120.78 (17)
N1ⁱⁱ—Na1—Na1ⁱⁱ	40.82 (3)	C12—C11—H11	119.6
Na1ⁱ—Na1—Na1ⁱⁱ	89.553 (3)	C10—C11—H11	119.6
C9—O1—Na1	124.17 (10)	C13—C12—C11	118.90 (17)
C9—O1—Na1ⁱⁱ	129.32 (11)	C13—C12—H12	120.5
Na1—O1—Na1ⁱⁱ	98.63 (5)	C11—C12—H12	120.5
C7—O2—C8	103.76 (12)	C12—C13—C14	122.05 (16)
C16—O5—Na1	135.43 (13)	C12—C13—N4	119.46 (17)
C16—O5—H5	110.6 (14)	C14—C13—N4	118.47 (16)
Na1—O5—H5	113.6 (14)	C13—C14—C15	118.46 (17)
C8—N1—N2	106.69 (13)	C13—C14—H14	120.8
C8—N1—Na1	121.22 (11)	C15—C14—H14	120.8
N2—N1—Na1	127.35 (10)	C14—C15—C10	121.27 (17)
C8—N1—Na1ⁱ	154.19 (11)	C14—C15—H15	119.4
N2—N1—Na1ⁱ	52.83 (7)	C10—C15—H15	119.4
Na1—N1—Na1ⁱ	84.17 (4)	O4—N4—O3	123.11 (17)
C7—N2—N1	106.93 (13)	O4—N4—C13	118.49 (17)
C7—N2—Na1ⁱ	148.36 (12)	O3—N4—C13	118.39 (17)
N1—N2—Na1ⁱ	99.56 (9)	O5—C16—H16A	109.5
C9—N3—C8	117.38 (13)	O5—C16—H16B	109.5
C2—C1—C6	120.4 (2)	H16A—C16—H16B	109.5
C2—C1—H1	119.8	O5—C16—H16C	109.5
C6—C1—H1	119.8	H16A—C16—H16C	109.5
C1—C2—C3	119.8 (2)	H16B—C16—H16C	109.5
C1—C2—H2	120.1

Symmetry codes: (i) y+3/4, −x+5/4, −z+1/4; (ii) −y+5/4, x−3/4, −z+1/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N3ⁱⁱⁱ	0.85 (1)	2.12 (1)	2.9534 (19)	167 (2)

Symmetry code: (iii) −x+3/2, −y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Na₄(C₁₅H₉N₄O₄)₄(CH₄O)₄]
M_r	1457.18
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	293
a, c (Å)	15.6635 (2), 27.1833 (6)
V (Å³)	6669.29 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.934, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15582, 3413, 2653
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.02
No. of reflections	3413
No. of parameters	239
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Selected bond lengths (Å) top

Na1—O5	2.3413 (14)	Na1—N1ⁱⁱ	2.9859 (15)
Na1—N1	2.3828 (15)	O1—Na1ⁱⁱ	2.3972 (13)
Na1—O1	2.3848 (13)	N1—Na1ⁱ	2.9859 (15)
Na1—O1ⁱ	2.3972 (13)	N2—Na1ⁱ	2.4127 (15)
Na1—N2ⁱⁱ	2.4127 (15)

Symmetry codes: (i) y+3/4, −x+5/4, −z+1/4; (ii) −y+5/4, x−3/4, −z+1/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N3ⁱⁱⁱ	0.847 (8)	2.121 (10)	2.9534 (19)	167.3 (19)

Symmetry code: (iii) −x+3/2, −y+1/2, −z+1/2.

Acknowledgements

This work was supported by a start-up grant from Luoyang Institute of Science and Technology.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gibson, M. S. (1962). Tetrahedron, 18, 1377–1380. CrossRef CAS Web of Science Google Scholar
Hu, T. L., Du, W. P., Hu, B. W., Li, J. R., Bu, X. H. & Cao, R. (2008). CrystEngComm, 10, 1037–1043. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2004). 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
Zhang, F. L., Hou, Y. H., Du, C. X. & Wu, Y. J. (2009). Dalton Trans. pp. 7359–7367. Web of Science CSD CrossRef 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.