Poly[[μ-bis-(4-nitro-phen-yl) phosphato-κ(2) O,O']sodium].

The title compound, [Na(C12H8N2O8P)], consists of one Na(+) cation and one bis-(p-nitro-phen-yl)phosphate anion with a considerable distortion of the phosphate tetra-hedron due to the presence of two P-O ester bonds. The anion bridges five Na(+) cations whereby each cation is chelated by the nitro O atoms of one anion and bonded via a nitro O atom and phosphate O atoms to four other anions. This bridging arrangement leads to the formation of double layers parallel to (001). Adjacent layers are linked through weak C-H⋯O hydrogen bonds.

Related literature

For hydrolytic cleavage of the phospho­diester bond in bis­(p-nitro­phen­yl)phosphate (BNPP) and related systems, see: Belousoff et al. (2009 ▶); Branum et al. (2001 ▶); Chang et al. (2009 ▶); Liu et al. (2004 ▶); Mancin et al. (2005 ▶); Oh et al. (1996 ▶); Sredhera & Cowan (2001 ▶). For crystal structures containing the BNPP entity, see: Bazzicalupi et al. (2004 ▶); Bond et al. (1985 ▶); Fry et al. (2003 ▶); Jurek & Martell (1999 ▶); Král et al. (2006 ▶); Pletcher et al. (1972 ▶); Sax et al. (1970 ▶, 1971 ▶); Warden et al. (2005 ▶); Yoo et al. (1975 ▶).

Experimental

Crystal data

[Na(C12H8N2O8P)]

M = 362.16

Triclinic,

a = 6.963 (2) Å

b = 9.844 (3) Å

c = 11.213 (3) Å

α = 103.93 (3)°

β = 105.83 (3)°

γ = 106.38 (3)°

V = 666.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.30 × 0.27 × 0.25 mm

Data collection

Agilent Xcalibur (Onyx with CCD camera) diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.918, T max = 0.931

13418 measured reflections

6748 independent reflections

5542 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.090

S = 1.07

6748 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813019260/wm2751sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019260/wm2751Isup2.hkl

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

[Na(C12H8N2O8P)]	Z = 2
Mr = 362.16	F(000) = 368
Triclinic, P1	Dx = 1.806 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.963 (2) Å	Cell parameters from 8925 reflections
b = 9.844 (3) Å	θ = 3.2–37.5°
c = 11.213 (3) Å	µ = 0.29 mm−1
α = 103.93 (3)°	T = 100 K
β = 105.83 (3)°	Block, yellow
γ = 106.38 (3)°	0.30 × 0.27 × 0.25 mm
V = 666.1 (3) Å3

Agilent Xcalibur (Onyx with CCD camera) diffractometer	6748 independent reflections
Radiation source: fine-focus sealed tube	5542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ω and π scans	θmax = 37.6°, θmin = 3.2°
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	h = −11→10
Tmin = 0.918, Tmax = 0.931	k = −16→15
13418 measured reflections	l = −19→15

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0486P)2 + 0.1337P] where P = (Fo2 + 2Fc2)/3
6748 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.33 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
P1	0.19163 (3)	0.36887 (2)	0.291283 (19)	0.00783 (4)
O1	0.52988 (11)	1.11256 (7)	0.18582 (7)	0.01642 (12)
O2	0.66594 (11)	1.15233 (7)	0.39510 (6)	0.01488 (11)
O3	−0.28509 (13)	−0.46498 (7)	0.15506 (8)	0.02195 (14)
O4	−0.14079 (12)	−0.34783 (8)	0.36644 (7)	0.01817 (13)
O11	0.18884 (10)	0.45097 (6)	0.18143 (6)	0.01210 (10)
O21	0.02554 (10)	0.20680 (6)	0.18007 (6)	0.01107 (10)
O31	0.40483 (10)	0.36277 (7)	0.34892 (6)	0.01340 (11)
O41	0.08681 (9)	0.42769 (7)	0.37940 (6)	0.01131 (10)
N1	0.55665 (11)	1.06716 (8)	0.27967 (7)	0.01084 (11)
N2	−0.18533 (12)	−0.34891 (8)	0.25185 (8)	0.01290 (12)
C1	0.28334 (12)	0.60309 (8)	0.21207 (7)	0.00932 (12)
C2	0.24915 (13)	0.65553 (9)	0.10570 (8)	0.01132 (12)
H2	0.1654	0.5862	0.0187	0.014*
C3	0.33698 (13)	0.80825 (9)	0.12681 (8)	0.01110 (12)
H3	0.3144	0.8448	0.0551	0.013*
C4	0.45900 (12)	0.90670 (8)	0.25538 (8)	0.00970 (12)
C5	0.49639 (13)	0.85587 (9)	0.36171 (8)	0.01053 (12)
H5	0.5815	0.9255	0.4484	0.013*
C6	0.40903 (13)	0.70311 (9)	0.34079 (8)	0.01043 (12)
H6	0.4341	0.6669	0.4126	0.013*
C11	−0.01420 (12)	0.07325 (8)	0.20306 (8)	0.00914 (11)
C21	−0.14071 (13)	−0.05705 (9)	0.09256 (8)	0.01090 (12)
H21	−0.1902	−0.0492	0.0077	0.013*
C31	−0.19405 (13)	−0.19754 (9)	0.10643 (8)	0.01187 (13)
H31	−0.2790	−0.2867	0.0320	0.014*
C41	−0.11984 (13)	−0.20435 (9)	0.23230 (8)	0.01057 (12)
C51	0.00777 (13)	−0.07667 (9)	0.34263 (8)	0.01163 (13)
H51	0.0579	−0.0854	0.4271	0.014*
C61	0.06168 (13)	0.06395 (9)	0.32862 (8)	0.01120 (12)
H61	0.1489	0.1526	0.4033	0.013*
Na	0.75570 (5)	1.41177 (4)	0.39243 (3)	0.01082 (7)

	U11	U22	U33	U12	U13	U23
P1	0.00772 (8)	0.00661 (8)	0.00894 (8)	0.00226 (6)	0.00311 (6)	0.00274 (6)
O1	0.0212 (3)	0.0124 (3)	0.0172 (3)	0.0056 (2)	0.0065 (2)	0.0091 (2)
O2	0.0167 (3)	0.0091 (2)	0.0144 (3)	0.0027 (2)	0.0032 (2)	0.0020 (2)
O3	0.0321 (4)	0.0079 (3)	0.0231 (3)	0.0030 (3)	0.0129 (3)	0.0025 (2)
O4	0.0225 (3)	0.0154 (3)	0.0206 (3)	0.0075 (2)	0.0087 (3)	0.0116 (2)
O11	0.0172 (3)	0.0066 (2)	0.0100 (2)	0.00113 (19)	0.0046 (2)	0.00292 (18)
O21	0.0137 (2)	0.0062 (2)	0.0103 (2)	0.00136 (19)	0.00201 (19)	0.00335 (18)
O31	0.0084 (2)	0.0132 (3)	0.0176 (3)	0.0045 (2)	0.0038 (2)	0.0042 (2)
O41	0.0108 (2)	0.0121 (2)	0.0121 (2)	0.00466 (19)	0.00572 (19)	0.00352 (19)
N1	0.0107 (3)	0.0084 (3)	0.0147 (3)	0.0041 (2)	0.0052 (2)	0.0049 (2)
N2	0.0142 (3)	0.0093 (3)	0.0190 (3)	0.0054 (2)	0.0094 (2)	0.0063 (2)
C1	0.0102 (3)	0.0068 (3)	0.0107 (3)	0.0024 (2)	0.0041 (2)	0.0031 (2)
C2	0.0127 (3)	0.0092 (3)	0.0100 (3)	0.0020 (2)	0.0031 (2)	0.0035 (2)
C3	0.0123 (3)	0.0092 (3)	0.0111 (3)	0.0031 (2)	0.0036 (2)	0.0044 (2)
C4	0.0101 (3)	0.0072 (3)	0.0122 (3)	0.0031 (2)	0.0044 (2)	0.0038 (2)
C5	0.0119 (3)	0.0078 (3)	0.0106 (3)	0.0031 (2)	0.0035 (2)	0.0025 (2)
C6	0.0123 (3)	0.0086 (3)	0.0097 (3)	0.0031 (2)	0.0037 (2)	0.0035 (2)
C11	0.0094 (3)	0.0073 (3)	0.0110 (3)	0.0029 (2)	0.0039 (2)	0.0036 (2)
C21	0.0126 (3)	0.0084 (3)	0.0101 (3)	0.0025 (2)	0.0036 (2)	0.0028 (2)
C31	0.0136 (3)	0.0082 (3)	0.0124 (3)	0.0025 (2)	0.0054 (3)	0.0024 (2)
C41	0.0121 (3)	0.0074 (3)	0.0142 (3)	0.0040 (2)	0.0068 (2)	0.0046 (2)
C51	0.0130 (3)	0.0104 (3)	0.0118 (3)	0.0040 (2)	0.0040 (2)	0.0053 (2)
C61	0.0130 (3)	0.0086 (3)	0.0099 (3)	0.0024 (2)	0.0027 (2)	0.0031 (2)
Na	0.00911 (14)	0.00915 (14)	0.01433 (15)	0.00301 (11)	0.00447 (12)	0.00451 (12)

P1—O31	1.4733 (8)	C2—C3	1.3861 (12)
P1—O41	1.4834 (7)	C2—H2	0.9500
P1—O11	1.6266 (8)	C3—C4	1.3908 (14)
P1—O21	1.6287 (12)	C3—H3	0.9500
O1—N1	1.2282 (10)	C4—C5	1.3895 (12)
O1—Na	2.9377 (18)	C5—C6	1.3867 (12)
O2—N1	1.2399 (12)	C5—H5	0.9500
O2—Na	2.4618 (11)	C6—H6	0.9500
O3—N2	1.2288 (12)	C11—C61	1.3976 (12)
O4—N2	1.2335 (11)	C11—C21	1.3995 (14)
O4—Nai	2.3853 (11)	C21—C31	1.3857 (12)
O11—C1	1.3663 (11)	C21—H21	0.9500
O21—C11	1.3668 (10)	C31—C41	1.3894 (12)
O31—Naii	2.2386 (10)	C31—H31	0.9500
O41—Naiii	2.3135 (9)	C41—C51	1.3862 (14)
O41—Naiv	2.4065 (14)	C51—C61	1.3877 (12)
N1—C4	1.4552 (12)	C51—H51	0.9500
N2—C41	1.4560 (12)	C61—H61	0.9500
C1—C2	1.3987 (12)	Na—Nav	3.253 (2)
C1—C6	1.3998 (14)
O31—P1—O41	119.67 (5)	C1—C6—H6	120.6
O31—P1—O11	110.86 (4)	O21—C11—C61	123.21 (8)
O41—P1—O11	110.02 (4)	O21—C11—C21	116.04 (7)
O31—P1—O21	110.48 (5)	C61—C11—C21	120.74 (8)
O41—P1—O21	110.21 (4)	C31—C21—C11	120.28 (8)
O11—P1—O21	92.20 (4)	C31—C21—H21	119.9
N1—O1—Na	83.76 (6)	C11—C21—H21	119.9
N1—O2—Na	106.72 (6)	C21—C31—C41	118.15 (8)
N2—O4—Nai	116.10 (7)	C21—C31—H31	120.9
C1—O11—P1	123.69 (6)	C41—C31—H31	120.9
C11—O21—P1	123.67 (6)	C51—C41—C31	122.37 (8)
P1—O31—Naii	157.93 (4)	C51—C41—N2	117.95 (8)
P1—O41—Naiii	143.20 (5)	C31—C41—N2	119.61 (8)
P1—O41—Naiv	129.49 (4)	C41—C51—C61	119.45 (8)
Naiii—O41—Naiv	87.11 (4)	C41—C51—H51	120.3
O1—N1—O2	122.74 (7)	C61—C51—H51	120.3
O1—N1—C4	119.12 (8)	C51—C61—C11	119.01 (8)
O2—N1—C4	118.13 (8)	C51—C61—H61	120.5
O1—N1—Na	72.71 (6)	C11—C61—H61	120.5
O2—N1—Na	50.43 (5)	O31vi—Na—O41vii	165.08 (3)
C4—N1—Na	167.00 (5)	O31vi—Na—O4viii	99.55 (4)
O3—N2—O4	123.14 (8)	O41vii—Na—O4viii	81.55 (4)
O3—N2—C41	119.25 (8)	O31vi—Na—O41iv	101.98 (5)
O4—N2—C41	117.59 (8)	O41vii—Na—O41iv	92.89 (4)
O11—C1—C2	115.91 (8)	O4viii—Na—O41iv	80.28 (4)
O11—C1—C6	123.34 (8)	O31vi—Na—O2	84.38 (4)
C2—C1—C6	120.75 (7)	O41vii—Na—O2	92.94 (4)
C3—C2—C1	120.25 (8)	O4viii—Na—O2	172.26 (3)
C3—C2—H2	119.9	O41iv—Na—O2	105.55 (4)
C1—C2—H2	119.9	O31vi—Na—O1	74.29 (5)
C2—C3—C4	118.44 (8)	O41vii—Na—O1	93.25 (4)
C2—C3—H3	120.8	O4viii—Na—O1	128.23 (3)
C4—C3—H3	120.8	O41iv—Na—O1	151.44 (3)
C5—C4—C3	121.88 (8)	O2—Na—O1	46.28 (3)
C5—C4—N1	118.65 (8)	O31vi—Na—N1	76.99 (4)
C3—C4—N1	119.43 (8)	O41vii—Na—N1	94.92 (4)
C6—C5—C4	119.77 (8)	O4viii—Na—N1	151.70 (3)
C6—C5—H5	120.1	O41iv—Na—N1	128.02 (4)
C4—C5—H5	120.1	O2—Na—N1	22.85 (2)
C5—C6—C1	118.90 (8)	O1—Na—N1	23.53 (2)
C5—C6—H6	120.6
O31—P1—O11—C1	−74.91 (8)	C4—C5—C6—C1	−0.33 (12)
O41—P1—O11—C1	59.73 (8)	O11—C1—C6—C5	−179.42 (7)
O21—P1—O11—C1	172.18 (6)	C2—C1—C6—C5	1.12 (12)
O31—P1—O21—C11	53.96 (7)	P1—O21—C11—C61	8.66 (11)
O41—P1—O21—C11	−80.51 (7)	P1—O21—C11—C21	−172.40 (6)
O11—P1—O21—C11	167.21 (6)	O21—C11—C21—C31	−178.45 (7)
P1—O11—C1—C2	−174.63 (6)	C61—C11—C21—C31	0.52 (12)
P1—O11—C1—C6	5.90 (11)	C11—C21—C31—C41	0.45 (12)
O11—C1—C2—C3	179.50 (7)	C21—C31—C41—C51	−1.26 (12)
C6—C1—C2—C3	−1.01 (12)	C21—C31—C41—N2	175.67 (7)
C1—C2—C3—C4	0.09 (12)	O3—N2—C41—C51	−174.72 (8)
C2—C3—C4—C5	0.72 (12)	O4—N2—C41—C51	6.77 (11)
C2—C3—C4—N1	178.70 (7)	O3—N2—C41—C31	8.22 (12)
O1—N1—C4—C5	177.82 (7)	O4—N2—C41—C31	−170.30 (8)
O2—N1—C4—C5	−1.43 (11)	C31—C41—C51—C61	1.08 (12)
O1—N1—C4—C3	−0.23 (11)	N2—C41—C51—C61	−175.90 (7)
O2—N1—C4—C3	−179.48 (7)	C41—C51—C61—C11	−0.07 (12)
C3—C4—C5—C6	−0.60 (12)	O21—C11—C61—C51	178.18 (7)
N1—C4—C5—C6	−178.60 (7)	C21—C11—C61—C51	−0.71 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ix	0.95	2.50	3.1865 (15)	129
C21—H21···O1x	0.95	2.53	3.3337 (18)	142

P1—O31	1.4733 (8)
P1—O41	1.4834 (7)
P1—O11	1.6266 (8)
P1—O21	1.6287 (12)
O1—Na	2.9377 (18)
O2—Na	2.4618 (11)
O4—Nai	2.3853 (11)
O31—Naii	2.2386 (10)
O41—Naiii	2.3135 (9)
O41—Naiv	2.4065 (14)

O31—P1—O41	119.67 (5)
O31—P1—O11	110.86 (4)
O41—P1—O11	110.02 (4)
O31—P1—O21	110.48 (5)
O41—P1—O21	110.21 (4)
O11—P1—O21	92.20 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3v	0.95	2.50	3.1865 (15)	129
C21—H21⋯O1vi	0.95	2.53	3.3337 (18)	142

Symmetry codes: (v) ; (vi) .