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In the solid-state structure of the title compound, C4H10N+·C14H10Cl2NO2-·H2O, the asymmetric unit contains one cation, one anion and a water mol­ecule. There is a network of hydrogen bonds which is similar to that found in the hydrated diethyl­ammonium diclofenac salt. A comparison is made of the molecular conformation of the anions in the two related structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101010022/na1521sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010022/na1521Isup2.hkl
Contains datablock I

CCDC reference: 174825

Comment top

The systematic structural work being carried out on diclofenac salts, a type of non-steroidal anti-inflammatory drug (Castellari & Sabatino, 1994, 1996; Castellari & Ottani, 1995, 1996, 1997a,b, 1998; Castellari, Feroci & Ottani, 1999; Castellari, Comelli & Ottani, 1999; Castellari et al., 2001) has important pharmaceutical implications, since the presence of polymorphic forms and/or hydrates influences the bioavailability of the drug.

As shown in Fig. 1, the asymmetric unit of the title compound, (I), contains one cation, one anion and a water molecule. The bond lenghts and angles of the anion are in good agreement with the corresponding values found in previous works. In particular, the carboxylate group shows a marked π delocalization. The diclofenac anion is stabilized, as usual, by two intramolecular hydrogen bonds between the amino group and atoms O1 and Cl1. In the pyrrolidinium cation, the N atom is shifted out of the plane of the four C atoms by 0.308 (5) Å, and C17 and C18 are out of the C4 plane by -0.101 (3) and 0.102 (3) Å, respectively

The C—N distances are normal, but the C—C bond lengths are shorter than expected. For the pyrrolidinium cation, a similar behaviour in the C—C distances was reported (Teske et al., 1996). Since, in both structures, the displacement parameters of the C atoms opposite the N atom are larger than those of the adjacent C atoms, the apparent contraction of the –C–C distances could be attributed to the average displacement parameters. Actually, the distances involving C18, the atom affected by the largest thermal motion, are the shortest; C15—C18 = 1.458 (4) Å and C17—C18 = 1.453 (4) Å.

The intermolecular hydrogen-bond network is similar to that recently reported for the hydrated diethylammonium diclofenac salt (HDEA·D·H2O) (Castellari et al., 2001). In both salts, anions, cations and water molecules are linked into two-dimensional networks lying in a plane, i.e. [001] and [100] for HDEA·D·H2O and HP·D·H2O, respectively. The intermolecular hydrogen-bond scheme involves four normal hydrogen bonds, one charge-assisted between the anion and the cation and three involving the water molecule, where the O1W atom acts as a donor towards the two carboxylate O atoms and as an acceptor towards the pyrrolidinium N atom.

A comparison of the molecular conformation of D in the two structures is of some interest. The degrees of freedom of the diclofenac anion can be described by the following dihedral angles between planes, the values being quoted for HDEA·D·H2O and HP·D·H2O, respectively: C1–C6/C1—N1—C7 = 16.5 (1) and 18.2 (3)°, C7–C12/C1—N1—C7 = 61.6 (1) and 49.5 (2)°, C1—C2–C6/C2—C13—C14 = 77.5 (1) and 79.0 (2)° and O1—C14—O2/C2—C13—C14 = 56.3 (2) and 52.6 (2)°. Inspection of these values shows that the largest difference in the molecular conformation of the anions occurs in the dihedral angle between the dichlorophenyl ring (C7–C12) and the C1/N1/C7 plane [the difference in torsion angles C1—N1—C7—C12 = 11.0 (2)°]. However, we note that the smaller steric hindrance of the pyrrolidinium cation, compared with that of diethylammonium, influences the crystal packing.

In HP·D·H2O, the average H···A distance is 1.84 (1) Å and the density is 1.389 Mg m-3. In contrast, the average H···A distance in HDEA·D·H2O is 1.90 (1) Å and the density is 1.280 Mg m -3. The higher packing efficiency in HP·D·H2O compared with HDEA·D·H2O most likely results in lower stresses to accomodate the anions in the crystals. This may consequently lead to the smaller twist angle between the two phenyl rings, viz. 60.68 (8) versus 72.4 (2)°.

Experimental top

Crystalline HP·D·H2O was prepared by mixing equivalent molar amounts of diclofenac acid and pyrrolidine. Crystals were obtained from a water solution.

Refinement top

The H1 atom and the H atom bonded to the N2 and O3W atoms were located from a difference synthesis and were refined isotropically. The remaining H atoms were placed in calculated positions and refined riding on their parent atoms.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson, 1976).

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) diagram of HP·D·H2O. Non-H atoms are represented by displacement ellipsoids of 50% probability and H atoms by spheres of arbitrary size.
(I) top
Crystal data top
C4H10N+·C14H10Cl2NO2·H2OF(000) = 808
Mr = 385.28Dx = 1.389 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.9631 (7) ÅCell parameters from 5166 reflections
b = 9.6845 (3) Åθ = 2.5–26.1°
c = 10.0505 (4) ŵ = 0.37 mm1
β = 93.134 (1)°T = 293 K
V = 1842.99 (12) Å3Blocks, colourless
Z = 40.5 × 0.5 × 0.4 mm
Data collection top
Bruker SMART 2000 CDD
diffractometer
2046 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.087
Graphite monochromatorθmax = 25.0°, θmin = 1.1°
/w scansh = 2222
17027 measured reflectionsk = 1111
3244 independent reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2) + (0.0776P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max = 0.037
3244 reflectionsΔρmax = 0.29 e Å3
247 parametersΔρmin = 0.30 e Å3
32 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0047 (10)
Crystal data top
C4H10N+·C14H10Cl2NO2·H2OV = 1842.99 (12) Å3
Mr = 385.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 18.9631 (7) ŵ = 0.37 mm1
b = 9.6845 (3) ÅT = 293 K
c = 10.0505 (4) Å0.5 × 0.5 × 0.4 mm
β = 93.134 (1)°
Data collection top
Bruker SMART 2000 CDD
diffractometer
2046 reflections with I > 2σ(I)
17027 measured reflectionsRint = 0.087
3244 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04132 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 0.89Δρmax = 0.29 e Å3
3244 reflectionsΔρmin = 0.30 e Å3
247 parameters
Special details top

Experimental. Data collection was performed by an area detector over the whole reflection sphere, but data reduction was performed up to 25 degs to preserve as many informations as possible. However, on data merging, several observations (>30%) have been assigned a null value (17027 measured reflections, 3244 are independent, but, out of these, only 2046 have intensities > 2 sigma).

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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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 (Å2) top
xyzUiso*/Ueq
Cl10.25198 (4)0.69551 (7)1.01753 (8)0.0610 (3)
Cl20.04070 (4)0.45113 (7)0.71787 (7)0.0515 (2)
O10.34634 (9)0.45728 (19)0.81873 (19)0.0555 (5)
O20.40697 (9)0.36771 (19)0.65867 (19)0.0535 (5)
N10.19438 (11)0.4871 (2)0.8218 (2)0.0429 (6)
H10.2406 (10)0.516 (3)0.835 (3)0.061 (9)*
C10.19075 (12)0.3413 (2)0.8098 (2)0.0357 (6)
C20.23255 (12)0.2770 (2)0.7167 (2)0.0374 (6)
C30.22812 (14)0.1350 (3)0.7035 (3)0.0471 (7)
H20.25540.09110.64210.057*
C40.18420 (15)0.0564 (3)0.7793 (3)0.0539 (8)
H30.18150.03880.76760.065*
C50.14485 (14)0.1205 (3)0.8715 (3)0.0477 (7)
H40.11600.06840.92400.057*
C60.14786 (13)0.2615 (3)0.8868 (3)0.0422 (7)
H50.12080.30390.94950.051*
C70.14377 (13)0.5670 (2)0.8811 (2)0.0362 (6)
C80.16313 (13)0.6694 (2)0.9756 (3)0.0398 (6)
C90.11463 (15)0.7520 (3)1.0338 (3)0.0468 (7)
H60.12960.81961.09460.056*
C100.04396 (15)0.7343 (3)1.0017 (3)0.0499 (7)
H70.01080.78611.04470.060*
C110.02229 (14)0.6398 (3)0.9060 (3)0.0465 (7)
H80.02550.62990.88210.056*
C120.07158 (13)0.5594 (2)0.8453 (3)0.0382 (6)
C130.28123 (13)0.3583 (3)0.6333 (3)0.0417 (6)
H90.25730.44180.60210.050*
H100.29200.30410.55580.050*
C140.35001 (13)0.3975 (2)0.7094 (3)0.0386 (6)
N20.46860 (12)0.0400 (2)0.7225 (2)0.0427 (6)
H110.5147 (9)0.061 (3)0.748 (3)0.081 (11)*
H120.4678 (15)0.019 (2)0.651 (2)0.068 (10)*
C150.42941 (15)0.1684 (3)0.6865 (3)0.0599 (8)
H130.39490.15190.61350.072*
H140.46150.24050.66080.072*
C160.43093 (15)0.0260 (3)0.8332 (3)0.0523 (7)
H150.46440.05580.90380.063*
H160.40410.10550.80060.063*
C170.38306 (19)0.0818 (3)0.8827 (4)0.0765 (10)
H170.39340.09800.97700.092*
H180.33420.05250.86980.092*
C180.3948 (2)0.2069 (3)0.8072 (4)0.0963 (14)
H190.35010.25200.78410.116*
H200.42440.27040.85990.116*
O1W0.43925 (11)0.1397 (2)0.5139 (2)0.0588 (6)
H1W0.420 (2)0.213 (3)0.559 (4)0.129 (16)*
H2W0.4037 (16)0.103 (3)0.455 (3)0.088 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0400 (4)0.0557 (5)0.0869 (6)0.0110 (3)0.0001 (4)0.0104 (4)
Cl20.0463 (4)0.0494 (4)0.0577 (5)0.0002 (3)0.0069 (3)0.0046 (3)
O10.0388 (11)0.0678 (13)0.0599 (14)0.0002 (9)0.0013 (9)0.0248 (11)
O20.0279 (11)0.0727 (13)0.0604 (13)0.0006 (9)0.0057 (9)0.0145 (10)
N10.0315 (13)0.0347 (12)0.0639 (16)0.0024 (10)0.0137 (11)0.0058 (11)
C10.0267 (14)0.0337 (14)0.0466 (16)0.0006 (11)0.0000 (12)0.0009 (12)
C20.0274 (14)0.0404 (15)0.0439 (16)0.0019 (11)0.0028 (12)0.0035 (12)
C30.0420 (17)0.0459 (17)0.0532 (18)0.0015 (13)0.0013 (14)0.0100 (14)
C40.0532 (19)0.0350 (15)0.073 (2)0.0016 (14)0.0033 (16)0.0029 (15)
C50.0410 (17)0.0400 (16)0.061 (2)0.0046 (13)0.0045 (14)0.0089 (14)
C60.0336 (15)0.0426 (16)0.0507 (17)0.0013 (12)0.0041 (13)0.0012 (13)
C70.0339 (15)0.0311 (13)0.0443 (16)0.0013 (11)0.0085 (12)0.0073 (12)
C80.0328 (15)0.0340 (14)0.0528 (17)0.0039 (11)0.0061 (12)0.0035 (12)
C90.0521 (19)0.0366 (14)0.0520 (18)0.0009 (13)0.0069 (14)0.0034 (13)
C100.0460 (18)0.0452 (17)0.060 (2)0.0126 (13)0.0125 (15)0.0005 (15)
C110.0362 (16)0.0435 (16)0.0601 (19)0.0051 (13)0.0049 (14)0.0047 (14)
C120.0374 (15)0.0330 (14)0.0444 (16)0.0005 (11)0.0045 (12)0.0016 (12)
C130.0308 (14)0.0509 (16)0.0438 (16)0.0020 (12)0.0042 (12)0.0009 (13)
C140.0317 (15)0.0355 (14)0.0484 (17)0.0016 (11)0.0017 (12)0.0028 (13)
N20.0350 (14)0.0495 (14)0.0436 (14)0.0021 (11)0.0026 (11)0.0035 (12)
C150.0507 (19)0.0571 (18)0.072 (2)0.0047 (15)0.0051 (16)0.0194 (16)
C160.062 (2)0.0486 (17)0.0474 (17)0.0001 (14)0.0073 (15)0.0053 (14)
C170.080 (3)0.067 (2)0.087 (3)0.0143 (18)0.039 (2)0.0117 (19)
C180.134 (4)0.067 (2)0.092 (3)0.047 (2)0.051 (3)0.017 (2)
O1W0.0595 (15)0.0687 (15)0.0479 (13)0.0180 (12)0.0003 (11)0.0010 (11)
Geometric parameters (Å, º) top
Cl1—C81.733 (3)C10—H70.9300
Cl2—C121.732 (3)C11—C121.384 (3)
O1—C141.248 (3)C11—H80.9300
O2—C141.253 (3)C13—C141.523 (3)
N1—C71.391 (3)C13—H90.9700
N1—C11.419 (3)C13—H100.9700
N1—H10.922 (17)N2—C151.483 (3)
C1—C61.388 (3)N2—C161.498 (3)
C1—C21.405 (3)N2—H110.921 (14)
C2—C31.383 (3)N2—H120.919 (13)
C2—C131.504 (3)C15—C181.458 (4)
C3—C41.387 (4)C15—H130.9700
C3—H20.9300C15—H140.9700
C4—C51.370 (4)C16—C171.487 (4)
C4—H30.9300C16—H150.9700
C5—C61.375 (3)C16—H160.9700
C5—H40.9300C17—C181.453 (4)
C6—H50.9300C17—H170.9700
C7—C121.398 (3)C17—H180.9700
C7—C81.408 (3)C18—H190.9700
C8—C91.374 (3)C18—H200.9700
C9—C101.372 (4)O1W—H1W0.93 (2)
C9—H60.9300O1W—H2W0.94 (2)
C10—C111.374 (4)
C7—N1—C1123.9 (2)C2—C13—H9109.1
C7—N1—H1116.4 (17)C14—C13—H9109.1
C1—N1—H1110.5 (17)C2—C13—H10109.1
C6—C1—C2119.5 (2)C14—C13—H10109.1
C6—C1—N1122.3 (2)H9—C13—H10107.8
C2—C1—N1118.1 (2)O1—C14—O2123.8 (2)
C3—C2—C1118.1 (2)O1—C14—C13118.1 (2)
C3—C2—C13120.2 (2)O2—C14—C13118.2 (2)
C1—C2—C13121.7 (2)C15—N2—C16106.6 (2)
C2—C3—C4121.9 (3)C15—N2—H11109.8 (18)
C2—C3—H2119.0C16—N2—H11112 (2)
C4—C3—H2119.0C15—N2—H12110.3 (18)
C5—C4—C3119.2 (3)C16—N2—H12109.0 (18)
C5—C4—H3120.4H11—N2—H12109 (3)
C3—C4—H3120.4C18—C15—N2104.7 (2)
C4—C5—C6120.3 (3)C18—C15—H13110.8
C4—C5—H4119.8N2—C15—H13110.8
C6—C5—H4119.8C18—C15—H14110.8
C5—C6—C1120.9 (3)N2—C15—H14110.8
C5—C6—H5119.6H13—C15—H14108.9
C1—C6—H5119.6C17—C16—N2105.9 (2)
N1—C7—C12123.3 (2)C17—C16—H15110.6
N1—C7—C8121.3 (2)N2—C16—H15110.6
C12—C7—C8115.2 (2)C17—C16—H16110.6
C9—C8—C7122.8 (2)N2—C16—H16110.6
C9—C8—Cl1118.4 (2)H15—C16—H16108.7
C7—C8—Cl1118.76 (19)C18—C17—C16107.3 (3)
C10—C9—C8119.7 (3)C18—C17—H17110.3
C10—C9—H6120.2C16—C17—H17110.3
C8—C9—H6120.2C18—C17—H18110.3
C9—C10—C11119.9 (3)C16—C17—H18110.3
C9—C10—H7120.0H17—C17—H18108.5
C11—C10—H7120.0C17—C18—C15108.0 (3)
C10—C11—C12120.0 (3)C17—C18—H19110.1
C10—C11—H8120.0C15—C18—H19110.1
C12—C11—H8120.0C17—C18—H20110.1
C11—C12—C7122.2 (2)C15—C18—H20110.1
C11—C12—Cl2117.2 (2)H19—C18—H20108.4
C7—C12—Cl2120.55 (19)H1W—O1W—H2W108 (3)
C2—C13—C14112.7 (2)
C7—N1—C1—C618.2 (4)C7—C8—C9—C101.2 (4)
C7—N1—C1—C2162.0 (2)Cl1—C8—C9—C10179.5 (2)
C6—C1—C2—C31.3 (3)C8—C9—C10—C113.8 (4)
N1—C1—C2—C3179.0 (2)C9—C10—C11—C122.2 (4)
C6—C1—C2—C13178.5 (2)C10—C11—C12—C72.3 (4)
N1—C1—C2—C131.3 (3)C10—C11—C12—Cl2175.8 (2)
C1—C2—C3—C40.2 (4)N1—C7—C12—C11179.9 (2)
C13—C2—C3—C4179.6 (2)C8—C7—C12—C114.7 (4)
C2—C3—C4—C51.1 (4)N1—C7—C12—Cl22.2 (3)
C3—C4—C5—C61.3 (4)C8—C7—C12—Cl2173.28 (17)
C4—C5—C6—C10.2 (4)C3—C2—C13—C14100.6 (3)
C2—C1—C6—C51.1 (4)C1—C2—C13—C1479.1 (3)
N1—C1—C6—C5179.1 (2)C2—C13—C14—O152.6 (3)
C1—N1—C7—C1252.4 (4)C2—C13—C14—O2127.4 (2)
C1—N1—C7—C8132.4 (3)C16—N2—C15—C1825.6 (3)
N1—C7—C8—C9178.5 (2)C15—N2—C16—C1714.5 (3)
C12—C7—C8—C93.0 (3)N2—C16—C17—C182.2 (4)
N1—C7—C8—Cl10.2 (3)C16—C17—C18—C1518.6 (5)
C12—C7—C8—Cl1175.39 (18)N2—C15—C18—C1727.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.92 (2)2.53 (3)2.983 (2)110 (2)
N1—H1···O10.92 (2)2.09 (3)2.898 (3)144 (2)
O1W—H1W···O20.93 (2)1.83 (2)2.733 (3)164 (4)
O1W—H2W···O1i0.94 (2)1.80 (2)2.730 (3)170 (3)
N2—H11···O2ii0.92 (1)1.85 (1)2.736 (3)162 (3)
N2—H12···O1W0.92 (1)1.86 (2)2.758 (2)164 (3)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC4H10N+·C14H10Cl2NO2·H2O
Mr385.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)18.9631 (7), 9.6845 (3), 10.0505 (4)
β (°) 93.134 (1)
V3)1842.99 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.5 × 0.5 × 0.4
Data collection
DiffractometerBruker SMART 2000 CDD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
17027, 3244, 2046
Rint0.087
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.105, 0.89
No. of reflections3244
No. of parameters247
No. of restraints32
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.30

Computer programs: SMART (Bruker, 1998), SMART, SAINT-Plus (Bruker, 1999), SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993), ORTEPII (Johnson, 1976).

Selected geometric parameters (Å, º) top
O1—C141.248 (3)C15—C181.458 (4)
O2—C141.253 (3)C16—C171.487 (4)
N2—C151.483 (3)C17—C181.453 (4)
N2—C161.498 (3)
O1—C14—O2123.8 (2)C17—C16—N2105.9 (2)
C15—N2—C16106.6 (2)C18—C17—C16107.3 (3)
C18—C15—N2104.7 (2)C17—C18—C15108.0 (3)
C7—N1—C1—C618.2 (4)C1—C2—C13—C1479.1 (3)
N1—C1—C2—C131.3 (3)C2—C13—C14—O152.6 (3)
C1—N1—C7—C1252.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.92 (2)2.53 (3)2.983 (2)110 (2)
N1—H1···O10.92 (2)2.09 (3)2.898 (3)144 (2)
O1W—H1W···O20.93 (2)1.83 (2)2.733 (3)164 (4)
O1W—H2W···O1i0.94 (2)1.80 (2)2.730 (3)170 (3)
N2—H11···O2ii0.92 (1)1.85 (1)2.736 (3)162 (3)
N2—H12···O1W0.92 (1)1.86 (2)2.758 (2)164 (3)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y1/2, z+3/2.
 

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