Tetra-kis[μ(3)-4-nitro-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamidato]tetra-kis-[methano-lsodium(I)].

In the title compound, [Na(4)(C(15)H(9)N(4)O(4))(4)(CH(3)OH)(4)], the N(3)O(3) environment around the Na(+) ion is distorted octa-hedral. In the unit cell, four Na(+) ions are bridged by four Schiff base anions, leading to a tetra-nuclear complex with -4 symmetry. O-H⋯N hydrogen bonds between the methanol mol-ecule 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 = 1457.18

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 1.02

3413 reflections

239 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014791/hp2035sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Na4(C15H9N4O4)4(CH4O)4]	Dx = 1.451 Mg m−3
Mr = 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

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

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(Fo2) + (0.0488P)2 + 3.8193P] where P = (Fo2 + 2Fc2)/3
3413 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.22 e Å−3
2 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) ; (ii) .