Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039992/bi2228sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039992/bi2228Isup2.hkl |
CCDC reference: 663745
Analytical grade imidazole (Aldrich) and 4-nitrophenol (Aldrich) were dissolved separately in water and methanol, respectively. The solutions were mixed in a 1:2 molar ratio and stirred at 323 K for several hours, then allowed to cool to room temperature. Crystals were obtained after two weeks by slow evaporation.
All H atoms were visible in difference Fourier maps. Those bonded to C atoms and carboxyl O atoms were placed at idealized positions and refined as riding [C—H = 0.97 or 0.98 Å, O—H = 0.82 Å, Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O)]. Those belonging to the water molecule were included in their as-found positions and refined with the O—H distance restrained to be 0.89 (1) Å and with Uiso(H) = 1.5Ueq(O).
Organic molecules with π electrons polarized by Lewis acid/base groups exhibit significant electric dipolar moments. This is convenient for the design of new materials with enhanced non-linear optical (NLO) properties. 4-Nitrophenol (4NP) can act as a π acceptor, forming π stacking compounds with other aromatic molecules, and is also a moderate acid which often gives rise to hydrogen-bonded compounds (Vembu et al., 2003). The synthesis and structural characterization of the title compound was carried out in an attempt to prepare a new molecular crystalline material with significant NLO properties. However, the compound crystallizes in a centrosymmetric space group, and no significant second harmonic intensity is observed.
The asymmetric unit (Fig. 1) contains two 4NP molecules and one imidazole (IM) molecule. The positions of the protons were established taking into account the C—O distances in each acidic hydroxyl group of the 4NP molecules, the Fourier difference density map and the overall charge neutrality of the compound. O—H···O and N—H···O hydrogen bonds give rise to zigzag chains running parallel to the c axis. In these chains, the repeat sequence comprises an imidazolium cation, a water molecule, a 4NP molecule and a 4-nitrophenolate (4NP–) anion, the latter two lying in a tail-to-tail arrangement. The 4NP– anions connect two different chains (running in opposite directions) via atoms O2 and O3, which are acceptors of two hydrogen bonds. A 2-D hydrogen bonded network is therefore established in the (100) plane.
For related literature, see: Vembu et al. (2003).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C3H5N2+·C6H4NO3−·C6H5NO3·H2O | F(000) = 760 |
Mr = 364.32 | Dx = 1.450 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8152 reflections |
a = 20.6543 (3) Å | θ = 2.3–28.0° |
b = 3.7998 (1) Å | µ = 0.12 mm−1 |
c = 21.6509 (3) Å | T = 273 K |
β = 100.832 (1)° | Block, colourless |
V = 1668.93 (6) Å3 | 0.32 × 0.22 × 0.20 mm |
Z = 4 |
Bruker APEX II CCD diffractometer | 5070 independent reflections |
Radiation source: fine-focus sealed tube | 3124 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 30.5°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −28→29 |
Tmin = 0.91, Tmax = 0.98 | k = −5→5 |
64485 measured reflections | l = −30→28 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.068P)2 + 0.4455P] where P = (Fo2 + 2Fc2)/3 |
5070 reflections | (Δ/σ)max < 0.001 |
242 parameters | Δρmax = 0.23 e Å−3 |
2 restraints | Δρmin = −0.20 e Å−3 |
C3H5N2+·C6H4NO3−·C6H5NO3·H2O | V = 1668.93 (6) Å3 |
Mr = 364.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.6543 (3) Å | µ = 0.12 mm−1 |
b = 3.7998 (1) Å | T = 273 K |
c = 21.6509 (3) Å | 0.32 × 0.22 × 0.20 mm |
β = 100.832 (1)° |
Bruker APEX II CCD diffractometer | 5070 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 3124 reflections with I > 2σ(I) |
Tmin = 0.91, Tmax = 0.98 | Rint = 0.037 |
64485 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 2 restraints |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.23 e Å−3 |
5070 reflections | Δρmin = −0.20 e Å−3 |
242 parameters |
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 | ||
N1 | 0.24632 (7) | 0.5142 (4) | 0.28812 (6) | 0.0453 (3) | |
H1 | 0.2309 | 0.6083 | 0.2522 | 0.054* | |
C1 | 0.21230 (8) | 0.4289 (5) | 0.33129 (8) | 0.0502 (4) | |
H1A | 0.1671 | 0.4605 | 0.3280 | 0.060* | |
N2 | 0.25219 (7) | 0.2912 (4) | 0.38017 (7) | 0.0501 (4) | |
H2 | 0.2409 | 0.2171 | 0.4141 | 0.075* | |
C2 | 0.31425 (9) | 0.2867 (5) | 0.36755 (9) | 0.0538 (4) | |
H2A | 0.3520 | 0.2024 | 0.3937 | 0.065* | |
C3 | 0.31050 (8) | 0.4270 (5) | 0.31036 (9) | 0.0518 (4) | |
H3 | 0.3455 | 0.4593 | 0.2894 | 0.062* | |
O1 | −0.08257 (6) | 0.3716 (5) | 0.14603 (6) | 0.0713 (4) | |
O2 | −0.06841 (7) | 0.3946 (5) | 0.05064 (7) | 0.0805 (5) | |
N3 | −0.04774 (7) | 0.3245 (4) | 0.10640 (7) | 0.0488 (4) | |
C4 | 0.01766 (7) | 0.1921 (4) | 0.12502 (7) | 0.0391 (3) | |
C5 | 0.05858 (8) | 0.1678 (5) | 0.08089 (7) | 0.0449 (4) | |
H5 | 0.0433 | 0.2346 | 0.0394 | 0.054* | |
C6 | 0.12145 (8) | 0.0447 (5) | 0.09921 (7) | 0.0457 (4) | |
H6A | 0.1488 | 0.0305 | 0.0698 | 0.055* | |
C7 | 0.14569 (7) | −0.0610 (4) | 0.16142 (7) | 0.0384 (3) | |
O3 | 0.20579 (5) | −0.1830 (3) | 0.17899 (5) | 0.0489 (3) | |
C8 | 0.10277 (8) | −0.0309 (5) | 0.20472 (7) | 0.0443 (4) | |
H8 | 0.1175 | −0.0983 | 0.2463 | 0.053* | |
C9 | 0.04013 (8) | 0.0946 (5) | 0.18709 (7) | 0.0444 (4) | |
H9 | 0.0127 | 0.1146 | 0.2164 | 0.053* | |
O4 | 0.54689 (7) | 0.4274 (5) | 0.17607 (8) | 0.0818 (5) | |
O5 | 0.54652 (7) | 0.3441 (5) | 0.07800 (8) | 0.0848 (5) | |
N4 | 0.52012 (7) | 0.3238 (4) | 0.12386 (8) | 0.0580 (4) | |
C10 | 0.45462 (8) | 0.1720 (4) | 0.11626 (8) | 0.0443 (4) | |
C11 | 0.42407 (8) | 0.1463 (5) | 0.16755 (8) | 0.0478 (4) | |
H11 | 0.4454 | 0.2222 | 0.2070 | 0.057* | |
C12 | 0.36168 (8) | 0.0070 (5) | 0.15963 (8) | 0.0461 (4) | |
H12 | 0.3407 | −0.0114 | 0.1939 | 0.055* | |
C13 | 0.32958 (7) | −0.1069 (4) | 0.10057 (7) | 0.0405 (3) | |
O6 | 0.26930 (5) | −0.2495 (4) | 0.09096 (6) | 0.0518 (3) | |
H6 | 0.2531 | −0.2223 | 0.1224 | 0.078* | |
C14 | 0.36155 (8) | −0.0784 (5) | 0.04971 (7) | 0.0469 (4) | |
H14 | 0.3405 | −0.1548 | 0.0102 | 0.056* | |
C15 | 0.42381 (8) | 0.0612 (5) | 0.05720 (8) | 0.0498 (4) | |
H15 | 0.4450 | 0.0810 | 0.0230 | 0.060* | |
O7 | 0.20602 (7) | 0.0530 (6) | 0.47937 (7) | 0.0836 (5) | |
H7A | 0.2284 (14) | −0.045 (8) | 0.5123 (11) | 0.125* | |
H7B | 0.1710 (11) | −0.045 (8) | 0.4664 (15) | 0.125* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0431 (7) | 0.0532 (8) | 0.0387 (7) | 0.0022 (6) | 0.0053 (6) | 0.0022 (6) |
C1 | 0.0390 (9) | 0.0647 (11) | 0.0467 (9) | 0.0071 (8) | 0.0079 (7) | 0.0063 (8) |
N2 | 0.0506 (8) | 0.0570 (9) | 0.0422 (8) | 0.0052 (7) | 0.0076 (6) | 0.0069 (6) |
C2 | 0.0425 (9) | 0.0606 (11) | 0.0541 (11) | 0.0073 (8) | −0.0015 (8) | 0.0010 (8) |
C3 | 0.0389 (9) | 0.0635 (11) | 0.0536 (10) | 0.0010 (8) | 0.0103 (8) | −0.0019 (9) |
O1 | 0.0507 (7) | 0.1097 (12) | 0.0596 (8) | 0.0178 (8) | 0.0265 (6) | 0.0075 (8) |
O2 | 0.0482 (8) | 0.1416 (15) | 0.0505 (8) | 0.0238 (9) | 0.0064 (6) | 0.0204 (9) |
N3 | 0.0396 (7) | 0.0647 (9) | 0.0439 (8) | 0.0027 (6) | 0.0121 (6) | 0.0044 (7) |
C4 | 0.0354 (8) | 0.0449 (8) | 0.0375 (8) | −0.0014 (6) | 0.0086 (6) | 0.0012 (6) |
C5 | 0.0435 (9) | 0.0617 (10) | 0.0301 (7) | 0.0036 (7) | 0.0082 (6) | 0.0062 (7) |
C6 | 0.0420 (8) | 0.0627 (10) | 0.0349 (8) | 0.0043 (7) | 0.0139 (7) | 0.0057 (7) |
C7 | 0.0377 (8) | 0.0418 (8) | 0.0359 (8) | −0.0026 (6) | 0.0071 (6) | 0.0003 (6) |
O3 | 0.0389 (6) | 0.0672 (8) | 0.0404 (6) | 0.0060 (5) | 0.0071 (5) | 0.0079 (5) |
C8 | 0.0497 (9) | 0.0544 (9) | 0.0292 (7) | 0.0040 (7) | 0.0083 (6) | 0.0048 (6) |
C9 | 0.0461 (9) | 0.0544 (9) | 0.0362 (8) | 0.0023 (7) | 0.0168 (7) | 0.0032 (7) |
O4 | 0.0519 (8) | 0.1126 (13) | 0.0765 (10) | −0.0197 (8) | 0.0008 (7) | −0.0298 (9) |
O5 | 0.0540 (8) | 0.1253 (15) | 0.0798 (11) | −0.0267 (9) | 0.0246 (8) | −0.0126 (10) |
N4 | 0.0405 (8) | 0.0639 (10) | 0.0682 (11) | −0.0034 (7) | 0.0065 (8) | −0.0075 (8) |
C10 | 0.0348 (8) | 0.0479 (9) | 0.0489 (9) | 0.0017 (7) | 0.0043 (7) | −0.0023 (7) |
C11 | 0.0464 (9) | 0.0543 (10) | 0.0398 (8) | −0.0001 (7) | 0.0002 (7) | −0.0051 (7) |
C12 | 0.0467 (9) | 0.0553 (10) | 0.0371 (8) | −0.0020 (7) | 0.0099 (7) | −0.0034 (7) |
C13 | 0.0356 (8) | 0.0449 (8) | 0.0403 (8) | 0.0038 (6) | 0.0055 (6) | −0.0018 (6) |
O6 | 0.0381 (6) | 0.0737 (8) | 0.0445 (7) | −0.0060 (6) | 0.0101 (5) | −0.0105 (6) |
C14 | 0.0432 (9) | 0.0627 (10) | 0.0341 (8) | −0.0011 (7) | 0.0048 (7) | −0.0066 (7) |
C15 | 0.0433 (9) | 0.0636 (11) | 0.0441 (9) | 0.0011 (8) | 0.0127 (7) | −0.0024 (8) |
O7 | 0.0493 (8) | 0.1412 (16) | 0.0569 (9) | −0.0156 (9) | 0.0011 (7) | 0.0356 (10) |
N1—C1 | 1.311 (2) | C8—C9 | 1.365 (2) |
N1—C3 | 1.364 (2) | C8—H8 | 0.930 |
N1—H1 | 0.860 | C9—H9 | 0.930 |
C1—N2 | 1.321 (2) | O4—N4 | 1.226 (2) |
C1—H1A | 0.930 | O5—N4 | 1.222 (2) |
N2—C2 | 1.360 (2) | N4—C10 | 1.451 (2) |
N2—H2 | 0.860 | C10—C11 | 1.380 (2) |
C2—C3 | 1.337 (3) | C10—C15 | 1.383 (2) |
C2—H2A | 0.930 | C11—C12 | 1.374 (2) |
C3—H3 | 0.930 | C11—H11 | 0.930 |
O1—N3 | 1.2320 (18) | C12—C13 | 1.394 (2) |
O2—N3 | 1.2316 (19) | C12—H12 | 0.930 |
N3—C4 | 1.427 (2) | C13—O6 | 1.3380 (18) |
C4—C9 | 1.387 (2) | C13—C14 | 1.391 (2) |
C4—C5 | 1.393 (2) | O6—H6 | 0.820 |
C5—C6 | 1.367 (2) | C14—C15 | 1.372 (2) |
C5—H5 | 0.930 | C14—H14 | 0.930 |
C6—C7 | 1.405 (2) | C15—H15 | 0.930 |
C6—H6A | 0.930 | O7—H7A | 0.86 (2) |
C7—O3 | 1.3125 (18) | O7—H7B | 0.82 (2) |
C7—C8 | 1.411 (2) | ||
C1—N1—C3 | 107.68 (14) | C9—C8—C7 | 121.58 (14) |
C1—N1—H1 | 126.2 | C9—C8—H8 | 119.2 |
C3—N1—H1 | 126.2 | C7—C8—H8 | 119.2 |
N1—C1—N2 | 109.38 (15) | C8—C9—C4 | 119.44 (14) |
N1—C1—H1A | 125.3 | C8—C9—H9 | 120.3 |
N2—C1—H1A | 125.3 | C4—C9—H9 | 120.3 |
C1—N2—C2 | 108.28 (15) | O5—N4—O4 | 122.41 (16) |
C1—N2—H2 | 125.9 | O5—N4—C10 | 118.82 (16) |
C2—N2—H2 | 125.9 | O4—N4—C10 | 118.77 (16) |
C3—C2—N2 | 106.76 (15) | C11—C10—C15 | 121.46 (15) |
C3—C2—H2A | 126.6 | C11—C10—N4 | 119.64 (15) |
N2—C2—H2A | 126.6 | C15—C10—N4 | 118.89 (15) |
C2—C3—N1 | 107.90 (15) | C12—C11—C10 | 119.15 (15) |
C2—C3—H3 | 126.1 | C12—C11—H11 | 120.4 |
N1—C3—H3 | 126.1 | C10—C11—H11 | 120.4 |
O2—N3—O1 | 120.74 (14) | C11—C12—C13 | 120.49 (15) |
O2—N3—C4 | 119.25 (13) | C11—C12—H12 | 119.8 |
O1—N3—C4 | 120.00 (14) | C13—C12—H12 | 119.8 |
C9—C4—C5 | 120.76 (14) | O6—C13—C14 | 118.35 (14) |
C9—C4—N3 | 119.64 (13) | O6—C13—C12 | 122.46 (14) |
C5—C4—N3 | 119.59 (14) | C14—C13—C12 | 119.18 (14) |
C6—C5—C4 | 119.30 (14) | C13—O6—H6 | 109.5 |
C6—C5—H5 | 120.3 | C15—C14—C13 | 120.68 (15) |
C4—C5—H5 | 120.3 | C15—C14—H14 | 119.7 |
C5—C6—C7 | 121.61 (14) | C13—C14—H14 | 119.7 |
C5—C6—H6A | 119.2 | C14—C15—C10 | 119.03 (15) |
C7—C6—H6A | 119.2 | C14—C15—H15 | 120.5 |
O3—C7—C6 | 121.74 (13) | C10—C15—H15 | 120.5 |
O3—C7—C8 | 120.94 (14) | H7A—O7—H7B | 113 (3) |
C6—C7—C8 | 117.31 (14) | ||
C3—N1—C1—N2 | 0.1 (2) | C5—C4—C9—C8 | −0.9 (3) |
N1—C1—N2—C2 | −0.3 (2) | N3—C4—C9—C8 | −179.83 (15) |
C1—N2—C2—C3 | 0.4 (2) | O5—N4—C10—C11 | 179.88 (18) |
N2—C2—C3—N1 | −0.4 (2) | O4—N4—C10—C11 | −0.2 (3) |
C1—N1—C3—C2 | 0.2 (2) | O5—N4—C10—C15 | −1.1 (3) |
O2—N3—C4—C9 | −176.55 (17) | O4—N4—C10—C15 | 178.77 (18) |
O1—N3—C4—C9 | 4.4 (3) | C15—C10—C11—C12 | 0.1 (3) |
O2—N3—C4—C5 | 4.5 (3) | N4—C10—C11—C12 | 179.04 (16) |
O1—N3—C4—C5 | −174.57 (17) | C10—C11—C12—C13 | 0.0 (3) |
C9—C4—C5—C6 | 0.3 (3) | C11—C12—C13—O6 | 178.85 (16) |
N3—C4—C5—C6 | 179.24 (16) | C11—C12—C13—C14 | 0.1 (3) |
C4—C5—C6—C7 | 0.6 (3) | O6—C13—C14—C15 | −179.06 (16) |
C5—C6—C7—O3 | 179.24 (16) | C12—C13—C14—C15 | −0.3 (3) |
C5—C6—C7—C8 | −0.8 (3) | C13—C14—C15—C10 | 0.3 (3) |
O3—C7—C8—C9 | −179.85 (16) | C11—C10—C15—C14 | −0.2 (3) |
C6—C7—C8—C9 | 0.2 (3) | N4—C10—C15—C14 | −179.21 (16) |
C7—C8—C9—C4 | 0.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.76 | 2.6198 (18) | 175 |
N2—H2···O7 | 0.86 | 1.81 | 2.667 (2) | 172 |
O6—H6···O3 | 0.82 | 1.71 | 2.5213 (15) | 169 |
O7—H7A···O6ii | 0.86 (2) | 1.92 (2) | 2.773 (2) | 173 (3) |
O7—H7B···O2iii | 0.82 (2) | 2.09 (2) | 2.858 (2) | 156 (3) |
Symmetry codes: (i) x, y+1, z; (ii) x, −y−1/2, z+1/2; (iii) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C3H5N2+·C6H4NO3−·C6H5NO3·H2O |
Mr | 364.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 20.6543 (3), 3.7998 (1), 21.6509 (3) |
β (°) | 100.832 (1) |
V (Å3) | 1668.93 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.32 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker APEX II CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.91, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 64485, 5070, 3124 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.714 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.157, 1.04 |
No. of reflections | 5070 |
No. of parameters | 242 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.20 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.76 | 2.6198 (18) | 175.3 |
N2—H2···O7 | 0.86 | 1.81 | 2.667 (2) | 172.3 |
O6—H6···O3 | 0.82 | 1.71 | 2.5213 (15) | 169.4 |
O7—H7A···O6ii | 0.86 (2) | 1.92 (2) | 2.773 (2) | 173 (3) |
O7—H7B···O2iii | 0.82 (2) | 2.09 (2) | 2.858 (2) | 156 (3) |
Symmetry codes: (i) x, y+1, z; (ii) x, −y−1/2, z+1/2; (iii) −x, y−1/2, −z+1/2. |
Organic molecules with π electrons polarized by Lewis acid/base groups exhibit significant electric dipolar moments. This is convenient for the design of new materials with enhanced non-linear optical (NLO) properties. 4-Nitrophenol (4NP) can act as a π acceptor, forming π stacking compounds with other aromatic molecules, and is also a moderate acid which often gives rise to hydrogen-bonded compounds (Vembu et al., 2003). The synthesis and structural characterization of the title compound was carried out in an attempt to prepare a new molecular crystalline material with significant NLO properties. However, the compound crystallizes in a centrosymmetric space group, and no significant second harmonic intensity is observed.
The asymmetric unit (Fig. 1) contains two 4NP molecules and one imidazole (IM) molecule. The positions of the protons were established taking into account the C—O distances in each acidic hydroxyl group of the 4NP molecules, the Fourier difference density map and the overall charge neutrality of the compound. O—H···O and N—H···O hydrogen bonds give rise to zigzag chains running parallel to the c axis. In these chains, the repeat sequence comprises an imidazolium cation, a water molecule, a 4NP molecule and a 4-nitrophenolate (4NP–) anion, the latter two lying in a tail-to-tail arrangement. The 4NP– anions connect two different chains (running in opposite directions) via atoms O2 and O3, which are acceptors of two hydrogen bonds. A 2-D hydrogen bonded network is therefore established in the (100) plane.