Disodium 4-nitro­phenyl phosphate trihydrate

The title compound, 2Na⁺·C₆H₄NO₆P²⁻·3H₂O, crystallizes from acetone with one 4-nitro­phenyl phosphate dianion, two Na⁺ cations and three water mol­ecules in the asymmetric unit. In the crystal packing, layers parallel to the ab plane are formed by Na⁺ cations chelated by dianions, and bridged by dianions and water mol­ecules. Adjacent layers are linked through O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.098
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.89
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  O5      ..       2.65 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C3     ..  O5      ..      97.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C5     ..  O6      ..      98.00 Deg.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.54 Ratio

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C6 H10 N1 Na2 O9 P1
            Atom count from _chemical_formula_moiety:C6 H10 N1 O9 P1

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 1998) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.

Disodium 4-nitrophenyl phosphate trihydrate

Crystal data

2Na^+·C6H4NO6P^2^−·3H2O	F(000) = 648
Mr = 317.10	Dx = 1.713 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 9496 reflections
a = 16.839 (4) Å	θ = 4.8–76.0°
b = 11.120 (3) Å	µ = 3.13 mm^−1
c = 6.693 (2) Å	T = 200 K
β = 101.11 (3)°	Plate, colourless
V = 1229.8 (6) Å^3	0.2 × 0.1 × 0.02 mm
Z = 4

Data collection

Oxford Xcalibur PX κ-geometry diffractometer with CCD Onyx camera	2294 independent reflections
Radiation source: fine-focus sealed tube	1834 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω and φ scans	θmax = 76.0°, θmin = 4.8°
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction 2003)	h = −21→16
Tmin = 0.663, Tmax = 0.933	k = −12→12
9754 measured reflections	l = −4→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0629P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2294 reflections	Δρmax = 0.30 e Å^−3
191 parameters	Δρmin = −0.39 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Na1	0.49331 (6)	0.66143 (8)	0.57156 (15)	0.0259 (2)
Na2	0.30726 (6)	0.77911 (8)	0.76399 (13)	0.0250 (2)
P	0.35859 (3)	0.49687 (5)	0.65260 (8)	0.01749 (17)
O1	0.30714 (10)	0.39500 (14)	0.4993 (3)	0.0242 (4)
O2	0.44385 (10)	0.46055 (14)	0.6469 (3)	0.0239 (4)
O3	0.33450 (10)	0.47778 (14)	0.8568 (2)	0.0236 (4)
O4	0.33680 (10)	0.61926 (13)	0.5644 (2)	0.0227 (4)
O5	−0.04400 (12)	0.2686 (2)	0.0617 (3)	0.0474 (5)
O6	−0.06515 (11)	0.4467 (2)	0.1683 (4)	0.0459 (5)
N	−0.02002 (13)	0.3613 (2)	0.1539 (3)	0.0333 (5)
C1	0.22619 (14)	0.3921 (2)	0.4220 (3)	0.0216 (5)
C2	0.19675 (14)	0.2854 (2)	0.3279 (4)	0.0254 (5)
H2	0.2325	0.2198	0.3231	0.031*
C3	0.11618 (15)	0.2741 (2)	0.2416 (4)	0.0285 (5)
H3	0.0956	0.2010	0.1786	0.034*
C4	0.06539 (14)	0.3719 (2)	0.2484 (4)	0.0264 (5)
C5	0.09307 (15)	0.4776 (2)	0.3448 (4)	0.0269 (5)
H5	0.0568	0.5424	0.3506	0.032*
C6	0.17395 (15)	0.4886 (2)	0.4331 (4)	0.0262 (5)
H6	0.1938	0.5608	0.5004	0.031*
O1W	0.23379 (11)	0.64341 (16)	0.9581 (3)	0.0285 (4)
H11	0.186 (2)	0.629 (3)	0.933 (5)	0.043*
H21	0.258 (2)	0.581 (3)	0.919 (5)	0.043*
O2W	0.42527 (11)	0.85678 (15)	0.6337 (3)	0.0275 (4)
H12	0.468 (2)	0.897 (3)	0.684 (5)	0.041*
H22	0.403 (2)	0.907 (3)	0.551 (6)	0.041*
O3W	0.57440 (11)	0.80747 (16)	0.3985 (3)	0.0277 (4)
H13	0.604 (2)	0.754 (3)	0.396 (5)	0.042*
H23	0.602 (2)	0.863 (3)	0.470 (6)	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0289 (5)	0.0233 (5)	0.0264 (5)	−0.0004 (4)	0.0073 (4)	−0.0005 (3)
Na2	0.0319 (5)	0.0228 (5)	0.0205 (4)	−0.0034 (4)	0.0055 (4)	−0.0041 (3)
P	0.0175 (3)	0.0157 (3)	0.0186 (3)	−0.0005 (2)	0.0017 (2)	0.00047 (19)
O1	0.0190 (8)	0.0193 (8)	0.0321 (9)	0.0009 (6)	−0.0007 (7)	−0.0048 (6)
O2	0.0183 (8)	0.0256 (8)	0.0273 (9)	−0.0010 (6)	0.0031 (6)	−0.0025 (6)
O3	0.0251 (9)	0.0250 (8)	0.0215 (8)	0.0025 (6)	0.0063 (6)	0.0041 (6)
O4	0.0303 (9)	0.0171 (8)	0.0201 (8)	−0.0003 (6)	0.0034 (6)	0.0026 (6)
O5	0.0333 (12)	0.0529 (13)	0.0503 (13)	−0.0109 (10)	−0.0064 (10)	−0.0130 (10)
O6	0.0216 (10)	0.0533 (13)	0.0591 (14)	0.0055 (9)	−0.0013 (9)	−0.0050 (10)
N	0.0222 (11)	0.0449 (13)	0.0311 (12)	−0.0043 (10)	0.0008 (9)	0.0015 (9)
C1	0.0193 (12)	0.0255 (11)	0.0193 (11)	−0.0017 (9)	0.0015 (9)	−0.0009 (8)
C2	0.0232 (12)	0.0257 (12)	0.0268 (12)	0.0004 (10)	0.0035 (9)	−0.0058 (9)
C3	0.0265 (13)	0.0308 (13)	0.0272 (12)	−0.0042 (10)	0.0027 (10)	−0.0061 (9)
C4	0.0180 (12)	0.0347 (13)	0.0252 (12)	−0.0031 (10)	0.0005 (9)	0.0010 (9)
C5	0.0212 (13)	0.0251 (12)	0.0332 (13)	0.0043 (9)	0.0021 (10)	−0.0004 (9)
C6	0.0248 (13)	0.0208 (12)	0.0322 (13)	0.0006 (9)	0.0031 (10)	−0.0036 (9)
O1W	0.0192 (9)	0.0308 (9)	0.0351 (10)	−0.0011 (7)	0.0044 (7)	−0.0059 (7)
O2W	0.0258 (9)	0.0231 (9)	0.0327 (10)	−0.0042 (7)	0.0030 (7)	0.0028 (6)
O3W	0.0301 (10)	0.0213 (9)	0.0304 (9)	0.0002 (7)	0.0028 (7)	−0.0051 (7)

Geometric parameters (Å, º)

Na1—O3W^i	2.371 (2)	O1—C1	1.362 (3)
Na1—O2^ii	2.386 (2)	O2—Na1^ii	2.3862 (19)
Na1—O2	2.470 (2)	O4—Na2^iii	2.2764 (18)
Na1—O2W	2.527 (2)	O5—N	1.230 (3)
Na1—O3W	2.540 (2)	O6—N	1.231 (3)
Na1—O4	2.668 (2)	N—C4	1.460 (3)
Na1—O2W^iii	2.941 (2)	C1—C2	1.390 (3)
Na1—P	3.0435 (12)	C1—C6	1.398 (3)
Na1—Na2^iii	3.465 (2)	C2—C3	1.374 (4)
Na1—Na1^ii	3.734 (2)	C2—H2	0.9500
Na1—Na2	3.839 (2)	C3—C4	1.389 (4)
Na1—Na1^i	3.8832 (13)	C3—H3	0.9500
Na2—O4^i	2.276 (2)	C4—C5	1.378 (4)
Na2—O4	2.334 (2)	C5—C6	1.382 (4)
Na2—O1W^iii	2.343 (2)	C5—H5	0.9500
Na2—O1W	2.473 (2)	C6—H6	0.9500
Na2—O2W	2.475 (2)	O1W—Na2^i	2.343 (2)
Na2—P	3.3766 (13)	O1W—H11	0.81 (4)
Na2—Na2^iii	3.4085 (10)	O1W—H21	0.87 (3)
Na2—Na2^i	3.4085 (10)	O2W—Na1^i	2.941 (2)
Na2—Na1^i	3.4647 (18)	O2W—H12	0.85 (4)
Na2—H21	2.63 (3)	O2W—H22	0.82 (4)
P—O1	1.6563 (17)	O3W—Na1^iii	2.371 (2)
P—O2	1.4989 (17)	O3W—H13	0.78 (4)
P—O3	1.5136 (17)	O3W—H23	0.86 (4)
P—O4	1.5006 (16)
O3W^i—Na1—O2^ii	113.83 (7)	O1W^iii—Na2—Na2^iii	46.51 (5)
O3W^i—Na1—O2	95.76 (7)	O1W—Na2—Na2^iii	119.64 (6)
O2^ii—Na1—O2	79.50 (7)	O2W—Na2—Na2^iii	64.43 (5)
O3W^i—Na1—O2W	85.49 (7)	O4^i—Na2—Na2^i	42.98 (4)
O2^ii—Na1—O2W	149.10 (7)	O4—Na2—Na2^i	117.23 (6)
O2—Na1—O2W	124.22 (7)	O1W^iii—Na2—Na2^i	145.89 (5)
O3W^i—Na1—O3W	93.61 (7)	O1W—Na2—Na2^i	43.42 (5)
O2^ii—Na1—O3W	75.13 (7)	O2W—Na2—Na2^i	124.35 (6)
O2—Na1—O3W	154.61 (7)	Na2^iii—Na2—Na2^i	158.10 (6)
O2W—Na1—O3W	79.98 (7)	O4^i—Na2—Na1^i	50.34 (5)
O3W^i—Na1—O4	115.68 (7)	O4—Na2—Na1^i	102.55 (6)
O2^ii—Na1—O4	116.25 (6)	O1W^iii—Na2—Na1^i	135.55 (6)
O2—Na1—O4	58.26 (5)	O1W—Na2—Na1^i	106.91 (6)
O2W—Na1—O4	71.13 (6)	O2W—Na2—Na1^i	56.44 (5)
O3W—Na1—O4	136.06 (7)	Na2^iii—Na2—Na1^i	116.65 (3)
O3W^i—Na1—O2W^iii	166.99 (7)	Na2^i—Na2—Na1^i	67.91 (3)
O2^ii—Na1—O2W^iii	58.92 (6)	O4^i—Na2—Na1	114.33 (6)
O2—Na1—O2W^iii	93.40 (6)	O4—Na2—Na1	43.18 (5)
O2W—Na1—O2W^iii	96.97 (7)	O1W^iii—Na2—Na1	99.19 (6)
O3W—Na1—O2W^iii	74.34 (6)	O1W—Na2—Na1	119.43 (6)
O4—Na1—O2W^iii	77.07 (6)	O2W—Na2—Na1	40.37 (5)
O3W^i—Na1—Na2^iii	144.54 (6)	Na2^iii—Na2—Na1	56.74 (3)
O2^ii—Na1—Na2^iii	101.62 (6)	Na2^i—Na2—Na1	114.77 (4)
O2—Na1—Na2^iii	89.54 (5)	Na1^i—Na2—Na1	63.99 (3)
O2W—Na1—Na2^iii	63.07 (5)	O2—P—O4	113.40 (10)
O3W—Na1—Na2^iii	96.38 (5)	O2—P—O3	114.20 (10)
O4—Na1—Na2^iii	41.06 (4)	O4—P—O3	113.24 (9)
O2W^iii—Na1—Na2^iii	44.52 (4)	O2—P—O1	100.91 (9)
O3W^i—Na1—Na1^ii	108.94 (6)	O4—P—O1	108.52 (9)
O2^ii—Na1—Na1^ii	40.57 (4)	O3—P—O1	105.31 (9)
O2—Na1—Na1^ii	38.93 (4)	C1—O1—P	128.11 (14)
O2W—Na1—Na1^ii	156.97 (6)	P—O2—Na1^ii	135.14 (10)
O3W—Na1—Na1^ii	115.69 (6)	P—O2—Na1	97.12 (8)
O4—Na1—Na1^ii	86.25 (5)	Na1^ii—O2—Na1	100.50 (7)
O2W^iii—Na1—Na1^ii	73.10 (5)	P—O4—Na2^iii	142.46 (10)
Na2^iii—Na1—Na1^ii	97.09 (4)	P—O4—Na2	121.91 (9)
O3W^i—Na1—Na2	90.15 (6)	Na2^iii—O4—Na2	95.34 (6)
O2^ii—Na1—Na2	152.40 (6)	P—O4—Na1	89.23 (8)
O2—Na1—Na2	84.88 (5)	Na2^iii—O4—Na1	88.60 (6)
O2W—Na1—Na2	39.36 (4)	Na2—O4—Na1	100.06 (6)
O3W—Na1—Na2	118.69 (6)	O5—N—O6	122.6 (2)
O4—Na1—Na2	36.77 (4)	O5—N—C4	119.1 (2)
O2W^iii—Na1—Na2	99.87 (5)	O6—N—C4	118.4 (2)
Na2^iii—Na1—Na2	55.35 (3)	O1—C1—C2	115.8 (2)
Na1^ii—Na1—Na2	120.48 (4)	O1—C1—C6	123.8 (2)
O3W^i—Na1—Na1^i	39.30 (5)	C2—C1—C6	120.4 (2)
O2^ii—Na1—Na1^i	152.88 (5)	C3—C2—C1	120.3 (2)
O2—Na1—Na1^i	103.11 (5)	C3—C2—H2	119.8
O2W—Na1—Na1^i	49.23 (5)	C1—C2—H2	119.8
O3W—Na1—Na1^i	99.08 (6)	C2—C3—C4	118.7 (2)
O4—Na1—Na1^i	86.59 (5)	C2—C3—H3	120.7
O2W^iii—Na1—Na1^i	146.00 (5)	C4—C3—H3	120.7
Na2^iii—Na1—Na1^i	105.37 (3)	C5—C4—C3	121.9 (2)
Na1^ii—Na1—Na1^i	135.96 (4)	C5—C4—N	119.2 (2)
Na2—Na1—Na1^i	53.31 (3)	C3—C4—N	119.0 (2)
O4^i—Na2—O4	148.12 (8)	C4—C5—C6	119.5 (2)
O4^i—Na2—O1W^iii	125.32 (7)	C4—C5—H5	120.3
O4—Na2—O1W^iii	85.11 (7)	C6—C5—H5	120.3
O4^i—Na2—O1W	83.41 (7)	C5—C6—C1	119.2 (2)
O4—Na2—O1W	91.11 (7)	C5—C6—H6	120.4
O1W^iii—Na2—O1W	116.75 (9)	C1—C6—H6	120.4
O4^i—Na2—O2W	94.84 (7)	Na2^i—O1W—Na2	90.08 (7)
O4—Na2—O2W	77.87 (7)	Na2—O2W—Na1	100.27 (7)
O1W^iii—Na2—O2W	83.59 (7)	Na2—O2W—Na1^i	79.04 (6)
O1W—Na2—O2W	156.23 (8)	Na1—O2W—Na1^i	90.17 (6)
O4^i—Na2—Na2^iii	156.95 (6)	Na1^iii—O3W—Na1	104.45 (8)
O4—Na2—Na2^iii	41.68 (4)
O2—P—O1—C1	−169.86 (19)	C3—C4—N—O5	−3.7 (4)
O3—P—O1—C1	71.1 (2)	C5—C4—N—O5	177.4 (2)
O4—P—O1—C1	−50.5 (2)	C3—C4—N—O6	177.0 (2)
P—O1—C1—C2	−168.62 (17)	C5—C4—N—O6	−1.9 (4)
P—O1—C1—C6	11.5 (3)	C6—C1—C2—C3	1.1 (4)
O1—C1—C2—C3	−178.8 (2)	C1—C2—C3—C4	0.8 (4)
O1—C1—C6—C5	178.3 (2)	C2—C3—C4—C5	−2.2 (4)
N—C4—C3—C2	178.9 (2)	C3—C4—C5—C6	1.7 (4)
N—C4—C5—C6	−179.4 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O6^iv	0.81 (4)	2.19 (4)	2.976 (3)	167 (3)
O1W—H11···O5^iv	0.81 (4)	2.65 (3)	3.321 (3)	141 (3)
O1W—H21···O3	0.87 (3)	1.83 (4)	2.678 (2)	164 (3)
O2W—H12···O2^v	0.85 (4)	1.83 (4)	2.664 (3)	164 (3)
O2W—H22···O3^iii	0.82 (4)	2.02 (4)	2.840 (3)	172 (3)
O3W—H13···O1^ii	0.78 (4)	2.25 (4)	2.998 (2)	161 (4)
O3W—H13···O2^ii	0.78 (4)	2.52 (4)	3.006 (3)	122 (3)
O3W—H23···O3^v	0.86 (4)	1.91 (4)	2.767 (2)	176 (3)
C3—H3···O5	0.95	2.45	2.735 (3)	97
C5—H5···O6	0.95	2.42	2.720 (3)	98
C5—H5···O5^vi	0.95	2.60	3.427 (3)	146
C6—H6···O4	0.95	2.45	3.078 (3)	124

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