Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023409/hy2061sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023409/hy2061Isup2.hkl |
CCDC reference: 620457
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (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
For general background, see: Prondzinski et al. 2007; Zaderenko et al. 1997. For a related structure, see: In et al. 1997.
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).
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).
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.
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.
Fig. 1. The asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. The crystal packing of (I). Dashed lines denote hydrogen bonds. |
Na+.C6H3NO5−.H2O | F(000) = 456 |
Mr = 224.11 | Dx = 1.851 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 3132 reflections |
a = 19.962 (3) Å | θ = 3.2–27.0° |
b = 11.4615 (17) Å | µ = 0.21 mm−1 |
c = 3.5291 (5) Å | T = 203 K |
β = 95.136 (12)° | Needle, yellow |
V = 804.2 (2) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Bruker SMART 1K CCD area-detector diffractometer | 971 independent reflections |
Radiation source: fine-focus sealed tube | 716 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
Detector resolution: 8.192 pixels mm-1 | θmax = 27.5°, θmin = 3.6° |
φ and ω scan | h = −25→25 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→14 |
Tmin = 0.959, Tmax = 0.979 | l = −4→4 |
5696 measured reflections |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.040 | H 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 parameters | Δρmax = 0.19 e Å−3 |
1 restraint | Δρmin = −0.22 e Å−3 |
Na+.C6H3NO5−.H2O | V = 804.2 (2) Å3 |
Mr = 224.11 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 19.962 (3) Å | µ = 0.21 mm−1 |
b = 11.4615 (17) Å | T = 203 K |
c = 3.5291 (5) Å | 0.20 × 0.10 × 0.10 mm |
β = 95.136 (12)° |
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 = 0.979 | Rint = 0.066 |
5696 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 1 restraint |
wR(F2) = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | Δρmax = 0.19 e Å−3 |
971 reflections | Δρmin = −0.22 e Å−3 |
145 parameters |
x | y | z | Uiso*/Ueq | ||
Na1 | −0.5000 | −0.10008 (15) | 0.0000 | 0.0181 (4) | |
Na2 | 0.0000 | −0.00873 (14) | 0.0000 | 0.0166 (5) | |
O5 | −0.07595 (10) | 0.03588 (16) | 0.4527 (6) | 0.0149 (5) | |
N1 | −0.34206 (13) | −0.1025 (2) | 0.1758 (7) | 0.0173 (7) | |
O1 | −0.06035 (10) | −0.18077 (16) | 0.7752 (6) | 0.0187 (6) | |
O4 | −0.38225 (10) | −0.03559 (17) | −0.0055 (6) | 0.0200 (6) | |
O3 | −0.12530 (9) | −0.3073 (2) | 0.4714 (5) | 0.0207 (5) | |
N2 | −0.11202 (13) | −0.2052 (2) | 0.5748 (7) | 0.0152 (6) | |
O2 | −0.35961 (10) | −0.19710 (18) | 0.3024 (6) | 0.0210 (6) | |
C1 | −0.25320 (16) | 0.0447 (3) | 0.1392 (8) | 0.0139 (8) | |
H1A | −0.2852 | 0.0976 | 0.0281 | 0.017* | |
C2 | −0.13592 (15) | 0.0009 (3) | 0.3809 (8) | 0.0120 (7) | |
C3 | −0.18714 (15) | 0.0772 (3) | 0.2110 (9) | 0.0132 (7) | |
H3A | −0.1748 | 0.1533 | 0.1457 | 0.016* | |
C4 | −0.22575 (15) | −0.1487 (3) | 0.3777 (8) | 0.0122 (8) | |
H4A | −0.2387 | −0.2256 | 0.4282 | 0.015* | |
C5 | −0.15992 (15) | −0.1149 (3) | 0.4466 (8) | 0.0123 (7) | |
C6 | −0.27234 (15) | −0.0690 (3) | 0.2343 (9) | 0.0117 (7) | |
O7 | −0.5000 | −0.2456 (3) | −0.5000 | 0.0178 (8) | |
O8 | −0.5000 | 0.0418 (3) | −0.5000 | 0.0181 (8) | |
H2 | −0.5300 (14) | 0.088 (3) | −0.511 (10) | 0.022 (10)* | |
H1 | −0.4654 (15) | −0.298 (3) | −0.498 (9) | 0.051 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Na1 | 0.0162 (11) | 0.0180 (10) | 0.0203 (11) | 0.000 | 0.0020 (8) | 0.000 |
Na2 | 0.0116 (10) | 0.0212 (11) | 0.0167 (11) | 0.000 | 0.0002 (8) | 0.000 |
O5 | 0.0122 (13) | 0.0141 (12) | 0.0178 (13) | −0.0009 (10) | −0.0013 (10) | −0.0014 (10) |
N1 | 0.0212 (18) | 0.0185 (16) | 0.0129 (16) | 0.0039 (15) | 0.0055 (13) | −0.0065 (14) |
O1 | 0.0119 (13) | 0.0183 (14) | 0.0236 (13) | −0.0022 (11) | −0.0113 (11) | −0.0010 (10) |
O4 | 0.0094 (13) | 0.0237 (14) | 0.0258 (15) | 0.0054 (10) | −0.0052 (11) | 0.0030 (11) |
O3 | 0.0187 (12) | 0.0143 (12) | 0.0288 (14) | 0.0007 (12) | −0.0004 (10) | −0.0036 (13) |
N2 | 0.0171 (17) | 0.0168 (16) | 0.0128 (15) | 0.0001 (13) | 0.0073 (13) | −0.0014 (13) |
O2 | 0.0166 (13) | 0.0165 (14) | 0.0298 (14) | −0.0059 (11) | 0.0012 (11) | 0.0006 (11) |
C1 | 0.0128 (19) | 0.0193 (19) | 0.010 (2) | 0.0038 (15) | 0.0013 (15) | 0.0007 (15) |
C2 | 0.0126 (19) | 0.0153 (18) | 0.0087 (18) | 0.0033 (16) | 0.0046 (15) | −0.0018 (14) |
C3 | 0.0162 (19) | 0.0113 (18) | 0.0127 (18) | −0.0015 (15) | 0.0054 (15) | 0.0026 (14) |
C4 | 0.0145 (19) | 0.0124 (17) | 0.0098 (18) | 0.0024 (14) | 0.0013 (14) | −0.0006 (13) |
C5 | 0.0108 (18) | 0.0160 (18) | 0.0096 (18) | 0.0045 (16) | −0.0012 (13) | 0.0002 (15) |
C6 | 0.0077 (19) | 0.017 (2) | 0.0101 (17) | −0.0032 (13) | −0.0011 (13) | −0.0018 (14) |
O7 | 0.016 (2) | 0.0138 (19) | 0.024 (2) | 0.000 | 0.0046 (17) | 0.000 |
O8 | 0.012 (2) | 0.013 (2) | 0.029 (2) | 0.000 | −0.0019 (18) | 0.000 |
Na1—O8i | 2.400 (3) | N1—O4 | 1.245 (3) |
Na1—O8 | 2.400 (3) | N1—C6 | 1.441 (4) |
Na1—O7 | 2.428 (2) | O1—N2 | 1.230 (3) |
Na1—O7i | 2.428 (2) | O3—N2 | 1.247 (3) |
Na1—O4 | 2.466 (2) | N2—C5 | 1.454 (4) |
Na1—O4ii | 2.466 (2) | C1—C3 | 1.372 (4) |
Na1—Na1i | 3.5291 (5) | C1—C6 | 1.407 (4) |
Na2—O5iii | 2.355 (2) | C1—H1A | 0.9400 |
Na2—O5 | 2.355 (2) | C2—C5 | 1.436 (4) |
Na2—O5iv | 2.401 (2) | C2—C3 | 1.435 (4) |
Na2—O5v | 2.401 (2) | C3—H3A | 0.9400 |
Na2—O1v | 2.408 (2) | C4—C5 | 1.371 (4) |
Na2—O1iv | 2.408 (2) | C4—C6 | 1.368 (4) |
Na2—Na2i | 3.5291 (5) | C4—H4A | 0.9400 |
O5—C2 | 1.267 (3) | O7—H1 | 0.92 (3) |
N1—O2 | 1.235 (3) | O8—H2 | 0.80 (3) |
O8i—Na1—O8 | 94.67 (14) | O5v—Na2—Na2i | 138.40 (5) |
O8i—Na1—O7 | 179.28 (11) | O1v—Na2—Na2i | 106.54 (5) |
O8—Na1—O7 | 86.05 (7) | O1iv—Na2—Na2i | 73.46 (5) |
O8i—Na1—O7i | 86.05 (7) | O5iii—Na2—Na2v | 42.60 (5) |
O8—Na1—O7i | 179.28 (11) | O5—Na2—Na2v | 137.40 (5) |
O7—Na1—O7i | 93.23 (12) | O5iv—Na2—Na2v | 138.40 (5) |
O8i—Na1—O4 | 82.26 (6) | O5v—Na2—Na2v | 41.60 (5) |
O8—Na1—O4 | 74.23 (6) | O1v—Na2—Na2v | 73.46 (5) |
O7—Na1—O4 | 97.94 (5) | O1iv—Na2—Na2v | 106.54 (5) |
O7i—Na1—O4 | 105.88 (5) | Na2i—Na2—Na2v | 180.00 (5) |
O8i—Na1—O4ii | 74.23 (6) | C2—O5—Na2 | 116.73 (18) |
O8—Na1—O4ii | 82.26 (6) | C2—O5—Na2i | 127.66 (19) |
O7—Na1—O4ii | 105.88 (5) | Na2—O5—Na2i | 95.80 (7) |
O7i—Na1—O4ii | 97.94 (5) | O2—N1—O4 | 122.4 (3) |
O4—Na1—O4ii | 145.11 (12) | O2—N1—C6 | 118.9 (3) |
O8i—Na1—Na1i | 42.67 (7) | O4—N1—C6 | 118.6 (3) |
O8—Na1—Na1i | 137.33 (7) | N2—O1—Na2i | 138.17 (18) |
O7—Na1—Na1i | 136.61 (6) | N1—O4—Na1 | 112.46 (18) |
O7i—Na1—Na1i | 43.39 (6) | O1—N2—O3 | 121.8 (2) |
O4—Na1—Na1i | 95.35 (5) | O1—N2—C5 | 120.8 (3) |
O4ii—Na1—Na1i | 84.65 (5) | O3—N2—C5 | 117.4 (2) |
O8i—Na1—Na1v | 137.33 (7) | C3—C1—C6 | 119.0 (3) |
O8—Na1—Na1v | 42.67 (7) | C3—C1—H1A | 120.5 |
O7—Na1—Na1v | 43.39 (6) | C6—C1—H1A | 120.5 |
O7i—Na1—Na1v | 136.61 (6) | O5—C2—C5 | 125.7 (3) |
O4—Na1—Na1v | 84.65 (5) | O5—C2—C3 | 121.0 (3) |
O4ii—Na1—Na1v | 95.35 (5) | C5—C2—C3 | 113.3 (3) |
Na1i—Na1—Na1v | 180.00 (6) | C1—C3—C2 | 123.3 (3) |
O5iii—Na2—O5 | 154.92 (12) | C1—C3—H3A | 118.4 |
O5iii—Na2—O5iv | 95.80 (7) | C2—C3—H3A | 118.4 |
O5—Na2—O5iv | 78.85 (8) | C5—C4—C6 | 119.1 (3) |
O5iii—Na2—O5v | 78.85 (8) | C5—C4—H4A | 120.4 |
O5—Na2—O5v | 95.80 (7) | C6—C4—H4A | 120.4 |
O5iv—Na2—O5v | 155.41 (11) | C4—C5—C2 | 124.1 (3) |
O5iii—Na2—O1v | 106.72 (7) | C4—C5—N2 | 116.6 (3) |
O5—Na2—O1v | 93.89 (8) | C2—C5—N2 | 119.2 (3) |
O5iv—Na2—O1v | 134.48 (8) | C4—C6—C1 | 121.1 (3) |
O5v—Na2—O1v | 69.40 (7) | C4—C6—N1 | 119.4 (3) |
O5iii—Na2—O1iv | 93.89 (8) | C1—C6—N1 | 119.5 (3) |
O5—Na2—O1iv | 106.72 (7) | Na1—O7—Na1v | 93.23 (12) |
O5iv—Na2—O1iv | 69.40 (7) | Na1—O7—H1 | 120 (2) |
O5v—Na2—O1iv | 134.48 (8) | Na1v—O7—H1 | 114 (2) |
O1v—Na2—O1iv | 70.04 (10) | Na1v—O8—Na1 | 94.67 (14) |
O5iii—Na2—Na2i | 137.40 (5) | Na1v—O8—H2 | 118 (2) |
O5—Na2—Na2i | 42.60 (5) | Na1—O8—H2 | 116 (2) |
O5iv—Na2—Na2i | 41.60 (5) |
Symmetry codes: (i) x, y, z+1; (ii) −x−1, y, −z; (iii) −x, y, −z; (iv) −x, y, −z+1; (v) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H2···O3vi | 0.80 (3) | 2.25 (3) | 3.035 (3) | 171 (3) |
O7—H1···O5vii | 0.92 (3) | 2.07 (3) | 2.925 (3) | 154 (3) |
Symmetry codes: (vi) x−1/2, y+1/2, z−1; (vii) −x−1/2, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | Na+.C6H3NO5−.H2O |
Mr | 224.11 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 203 |
a, b, c (Å) | 19.962 (3), 11.4615 (17), 3.5291 (5) |
β (°) | 95.136 (12) |
V (Å3) | 804.2 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.959, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5696, 971, 716 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.040, 0.90 |
No. of reflections | 971 |
No. of parameters | 145 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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.
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H2···O3i | 0.80 (3) | 2.25 (3) | 3.035 (3) | 171 (3) |
O7—H1···O5ii | 0.92 (3) | 2.07 (3) | 2.925 (3) | 154 (3) |
Symmetry codes: (i) x−1/2, y+1/2, z−1; (ii) −x−1/2, y−1/2, −z. |
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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.