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The title compound, Na+·C6H3N2O5-·H2O, was obtained by the reaction of sodium hydroxide with 2,4-dinitro­phenol in water. The crystal packing shows a laminated structure with inter­calated coordinated 2,4-dinitro­phenolate spacers, where Na+ cations and water mol­ecules lie on twofold rotation axes. The laminated structure consists of NaO6 chains linked by 2,4-dinitro­phenolate ligands. Each Na+ cation exhibits a distorted octa­hedral geometry. One cation is surrounded by four water mol­ecules and two O atoms from two 4-nitro groups. The other is surrounded by two O atoms from two 2-nitro groups and four phenolate O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023409/hy2061sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023409/hy2061Isup2.hkl
Contains datablock I

CCDC reference: 620457

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.032
  • wR factor = 0.040
  • Data-to-parameter ratio = 6.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.70 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.40 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.53 From the CIF: _reflns_number_total 971 Count of symmetry unique reflns 981 Completeness (_total/calc) 98.98% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

2,4-Dinitrophenolate is a versatile ligand for crystal engineering, which is able to coordinate with phenoxy or nitro groups to metal centers, yielding different metal complexes (Prondzinski et al., 2007; Zaderenko et al., 1997). It is known that nitrophenols not only form various π-stacking complexes with other aromatic molecules but also form salts through specific electrostatic or hydrogen-bonding interactions (In et al., 1997). The bonding of electron-donor-acceptor complexes depends strongly on the substitution pattern of nitro and hydroxy groups on the benzene ring.

The asymmetric unit of (I) is shown in Fig. 1, where Na atoms and water molecules each lies on a twofold rotation axis. The crystal packing of (I) shows a laminated structure with intercalated coordinated 2,4-dinitrophenolate spacer (Fig. 2). The laminated structure consists of NaO6 chains linked by 2,4-dinitrophenolate ligands. Each Na atom exhibits a distorted octahedral geometry. The Na1 atom is surrounded by four water molecules and two O atoms from two para-nitro groups. The Na2 atom is surrounded by two O atoms from two ortho-nitro groups and four phenolate O atoms.

Related literature top

For general background, see: Prondzinski et al. 2007; Zaderenko et al. 1997. For a related structure, see: In et al. 1997.

Experimental top

Compound (I) was obtained as the product of the reaction of sodium hydroxide (0.20 g, 5 mmol) with 2,4-dinitrophenol (0.70 g, 3.8 mmol) in water (10 ml) (yield 0.66 g).

Refinement top

H atoms on water molecules were located in a difference map and refined isotropically. The other H atoms were positioned geometrically and refined as riding, with C—H = 0.94 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

2,4-Dinitrophenolate is a versatile ligand for crystal engineering, which is able to coordinate with phenoxy or nitro groups to metal centers, yielding different metal complexes (Prondzinski et al., 2007; Zaderenko et al., 1997). It is known that nitrophenols not only form various π-stacking complexes with other aromatic molecules but also form salts through specific electrostatic or hydrogen-bonding interactions (In et al., 1997). The bonding of electron-donor-acceptor complexes depends strongly on the substitution pattern of nitro and hydroxy groups on the benzene ring.

The asymmetric unit of (I) is shown in Fig. 1, where Na atoms and water molecules each lies on a twofold rotation axis. The crystal packing of (I) shows a laminated structure with intercalated coordinated 2,4-dinitrophenolate spacer (Fig. 2). The laminated structure consists of NaO6 chains linked by 2,4-dinitrophenolate ligands. Each Na atom exhibits a distorted octahedral geometry. The Na1 atom is surrounded by four water molecules and two O atoms from two para-nitro groups. The Na2 atom is surrounded by two O atoms from two ortho-nitro groups and four phenolate O atoms.

For general background, see: Prondzinski et al. 2007; Zaderenko et al. 1997. For a related structure, see: In et al. 1997.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of (I). Dashed lines denote hydrogen bonds.
Sodium 2,4-dinitrophenolate Monohydrate top
Crystal data top
Na+.C6H3NO5.H2OF(000) = 456
Mr = 224.11Dx = 1.851 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 3132 reflections
a = 19.962 (3) Åθ = 3.2–27.0°
b = 11.4615 (17) ŵ = 0.21 mm1
c = 3.5291 (5) ÅT = 203 K
β = 95.136 (12)°Needle, yellow
V = 804.2 (2) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
971 independent reflections
Radiation source: fine-focus sealed tube716 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
Detector resolution: 8.192 pixels mm-1θmax = 27.5°, θmin = 3.6°
φ and ω scanh = 2525
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.959, Tmax = 0.979l = 44
5696 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.040H atoms treated by a mixture of independent and constrained refinement
S = 0.90 w = 1/[σ2(Fo2) + (0.0097P)2]
where P = (Fo2 + 2Fc2)/3
971 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.22 e Å3
Crystal data top
Na+.C6H3NO5.H2OV = 804.2 (2) Å3
Mr = 224.11Z = 4
Monoclinic, C2Mo Kα radiation
a = 19.962 (3) ŵ = 0.21 mm1
b = 11.4615 (17) ÅT = 203 K
c = 3.5291 (5) Å0.20 × 0.10 × 0.10 mm
β = 95.136 (12)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
971 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
716 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.979Rint = 0.066
5696 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0321 restraint
wR(F2) = 0.040H atoms treated by a mixture of independent and constrained refinement
S = 0.90Δρmax = 0.19 e Å3
971 reflectionsΔρmin = 0.22 e Å3
145 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Na10.50000.10008 (15)0.00000.0181 (4)
Na20.00000.00873 (14)0.00000.0166 (5)
O50.07595 (10)0.03588 (16)0.4527 (6)0.0149 (5)
N10.34206 (13)0.1025 (2)0.1758 (7)0.0173 (7)
O10.06035 (10)0.18077 (16)0.7752 (6)0.0187 (6)
O40.38225 (10)0.03559 (17)0.0055 (6)0.0200 (6)
O30.12530 (9)0.3073 (2)0.4714 (5)0.0207 (5)
N20.11202 (13)0.2052 (2)0.5748 (7)0.0152 (6)
O20.35961 (10)0.19710 (18)0.3024 (6)0.0210 (6)
C10.25320 (16)0.0447 (3)0.1392 (8)0.0139 (8)
H1A0.28520.09760.02810.017*
C20.13592 (15)0.0009 (3)0.3809 (8)0.0120 (7)
C30.18714 (15)0.0772 (3)0.2110 (9)0.0132 (7)
H3A0.17480.15330.14570.016*
C40.22575 (15)0.1487 (3)0.3777 (8)0.0122 (8)
H4A0.23870.22560.42820.015*
C50.15992 (15)0.1149 (3)0.4466 (8)0.0123 (7)
C60.27234 (15)0.0690 (3)0.2343 (9)0.0117 (7)
O70.50000.2456 (3)0.50000.0178 (8)
O80.50000.0418 (3)0.50000.0181 (8)
H20.5300 (14)0.088 (3)0.511 (10)0.022 (10)*
H10.4654 (15)0.298 (3)0.498 (9)0.051 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0162 (11)0.0180 (10)0.0203 (11)0.0000.0020 (8)0.000
Na20.0116 (10)0.0212 (11)0.0167 (11)0.0000.0002 (8)0.000
O50.0122 (13)0.0141 (12)0.0178 (13)0.0009 (10)0.0013 (10)0.0014 (10)
N10.0212 (18)0.0185 (16)0.0129 (16)0.0039 (15)0.0055 (13)0.0065 (14)
O10.0119 (13)0.0183 (14)0.0236 (13)0.0022 (11)0.0113 (11)0.0010 (10)
O40.0094 (13)0.0237 (14)0.0258 (15)0.0054 (10)0.0052 (11)0.0030 (11)
O30.0187 (12)0.0143 (12)0.0288 (14)0.0007 (12)0.0004 (10)0.0036 (13)
N20.0171 (17)0.0168 (16)0.0128 (15)0.0001 (13)0.0073 (13)0.0014 (13)
O20.0166 (13)0.0165 (14)0.0298 (14)0.0059 (11)0.0012 (11)0.0006 (11)
C10.0128 (19)0.0193 (19)0.010 (2)0.0038 (15)0.0013 (15)0.0007 (15)
C20.0126 (19)0.0153 (18)0.0087 (18)0.0033 (16)0.0046 (15)0.0018 (14)
C30.0162 (19)0.0113 (18)0.0127 (18)0.0015 (15)0.0054 (15)0.0026 (14)
C40.0145 (19)0.0124 (17)0.0098 (18)0.0024 (14)0.0013 (14)0.0006 (13)
C50.0108 (18)0.0160 (18)0.0096 (18)0.0045 (16)0.0012 (13)0.0002 (15)
C60.0077 (19)0.017 (2)0.0101 (17)0.0032 (13)0.0011 (13)0.0018 (14)
O70.016 (2)0.0138 (19)0.024 (2)0.0000.0046 (17)0.000
O80.012 (2)0.013 (2)0.029 (2)0.0000.0019 (18)0.000
Geometric parameters (Å, º) top
Na1—O8i2.400 (3)N1—O41.245 (3)
Na1—O82.400 (3)N1—C61.441 (4)
Na1—O72.428 (2)O1—N21.230 (3)
Na1—O7i2.428 (2)O3—N21.247 (3)
Na1—O42.466 (2)N2—C51.454 (4)
Na1—O4ii2.466 (2)C1—C31.372 (4)
Na1—Na1i3.5291 (5)C1—C61.407 (4)
Na2—O5iii2.355 (2)C1—H1A0.9400
Na2—O52.355 (2)C2—C51.436 (4)
Na2—O5iv2.401 (2)C2—C31.435 (4)
Na2—O5v2.401 (2)C3—H3A0.9400
Na2—O1v2.408 (2)C4—C51.371 (4)
Na2—O1iv2.408 (2)C4—C61.368 (4)
Na2—Na2i3.5291 (5)C4—H4A0.9400
O5—C21.267 (3)O7—H10.92 (3)
N1—O21.235 (3)O8—H20.80 (3)
O8i—Na1—O894.67 (14)O5v—Na2—Na2i138.40 (5)
O8i—Na1—O7179.28 (11)O1v—Na2—Na2i106.54 (5)
O8—Na1—O786.05 (7)O1iv—Na2—Na2i73.46 (5)
O8i—Na1—O7i86.05 (7)O5iii—Na2—Na2v42.60 (5)
O8—Na1—O7i179.28 (11)O5—Na2—Na2v137.40 (5)
O7—Na1—O7i93.23 (12)O5iv—Na2—Na2v138.40 (5)
O8i—Na1—O482.26 (6)O5v—Na2—Na2v41.60 (5)
O8—Na1—O474.23 (6)O1v—Na2—Na2v73.46 (5)
O7—Na1—O497.94 (5)O1iv—Na2—Na2v106.54 (5)
O7i—Na1—O4105.88 (5)Na2i—Na2—Na2v180.00 (5)
O8i—Na1—O4ii74.23 (6)C2—O5—Na2116.73 (18)
O8—Na1—O4ii82.26 (6)C2—O5—Na2i127.66 (19)
O7—Na1—O4ii105.88 (5)Na2—O5—Na2i95.80 (7)
O7i—Na1—O4ii97.94 (5)O2—N1—O4122.4 (3)
O4—Na1—O4ii145.11 (12)O2—N1—C6118.9 (3)
O8i—Na1—Na1i42.67 (7)O4—N1—C6118.6 (3)
O8—Na1—Na1i137.33 (7)N2—O1—Na2i138.17 (18)
O7—Na1—Na1i136.61 (6)N1—O4—Na1112.46 (18)
O7i—Na1—Na1i43.39 (6)O1—N2—O3121.8 (2)
O4—Na1—Na1i95.35 (5)O1—N2—C5120.8 (3)
O4ii—Na1—Na1i84.65 (5)O3—N2—C5117.4 (2)
O8i—Na1—Na1v137.33 (7)C3—C1—C6119.0 (3)
O8—Na1—Na1v42.67 (7)C3—C1—H1A120.5
O7—Na1—Na1v43.39 (6)C6—C1—H1A120.5
O7i—Na1—Na1v136.61 (6)O5—C2—C5125.7 (3)
O4—Na1—Na1v84.65 (5)O5—C2—C3121.0 (3)
O4ii—Na1—Na1v95.35 (5)C5—C2—C3113.3 (3)
Na1i—Na1—Na1v180.00 (6)C1—C3—C2123.3 (3)
O5iii—Na2—O5154.92 (12)C1—C3—H3A118.4
O5iii—Na2—O5iv95.80 (7)C2—C3—H3A118.4
O5—Na2—O5iv78.85 (8)C5—C4—C6119.1 (3)
O5iii—Na2—O5v78.85 (8)C5—C4—H4A120.4
O5—Na2—O5v95.80 (7)C6—C4—H4A120.4
O5iv—Na2—O5v155.41 (11)C4—C5—C2124.1 (3)
O5iii—Na2—O1v106.72 (7)C4—C5—N2116.6 (3)
O5—Na2—O1v93.89 (8)C2—C5—N2119.2 (3)
O5iv—Na2—O1v134.48 (8)C4—C6—C1121.1 (3)
O5v—Na2—O1v69.40 (7)C4—C6—N1119.4 (3)
O5iii—Na2—O1iv93.89 (8)C1—C6—N1119.5 (3)
O5—Na2—O1iv106.72 (7)Na1—O7—Na1v93.23 (12)
O5iv—Na2—O1iv69.40 (7)Na1—O7—H1120 (2)
O5v—Na2—O1iv134.48 (8)Na1v—O7—H1114 (2)
O1v—Na2—O1iv70.04 (10)Na1v—O8—Na194.67 (14)
O5iii—Na2—Na2i137.40 (5)Na1v—O8—H2118 (2)
O5—Na2—Na2i42.60 (5)Na1—O8—H2116 (2)
O5iv—Na2—Na2i41.60 (5)
Symmetry codes: (i) x, y, z+1; (ii) x1, y, z; (iii) x, y, z; (iv) x, y, z+1; (v) x, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H2···O3vi0.80 (3)2.25 (3)3.035 (3)171 (3)
O7—H1···O5vii0.92 (3)2.07 (3)2.925 (3)154 (3)
Symmetry codes: (vi) x1/2, y+1/2, z1; (vii) x1/2, y1/2, z.

Experimental details

Crystal data
Chemical formulaNa+.C6H3NO5.H2O
Mr224.11
Crystal system, space groupMonoclinic, C2
Temperature (K)203
a, b, c (Å)19.962 (3), 11.4615 (17), 3.5291 (5)
β (°) 95.136 (12)
V3)804.2 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART 1K CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.959, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
5696, 971, 716
Rint0.066
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.040, 0.90
No. of reflections971
No. of parameters145
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.22

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL and local programs.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H2···O3i0.80 (3)2.25 (3)3.035 (3)171 (3)
O7—H1···O5ii0.92 (3)2.07 (3)2.925 (3)154 (3)
Symmetry codes: (i) x1/2, y+1/2, z1; (ii) x1/2, y1/2, z.
 

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