17 salts of ephedrine: crystal structures and packing analysis

The structures of two neutral and 17 salt forms of the base (1R, 2S)-(−)-ephedrine are reported. These structures are discussed in the light of the conformers of the ephedrine moiety, the existence of bilayers and the structure determining role of the counterions. Overall, most of the salt structures are essentially derived from the observed packing of the neutral base and are dominated by the amphiphilic nature of the ephedrine molecular structure. In a few cases the size and hydrophobicity of the counterion disrupts this behaviour.

1. Introduction

The importance of molecular salts as solid forms in pharmaceutical formulations is well known (Stahl & Wermuth, 2002). For a given active ingredient, the isolation and selection of a salt with the appropriate physicochemical properties involves significant screening activity and has been discussed at some length in the literature (Tong & Whitesell, 1998; Shanker, 1994). It is apparent that over 40% of marketed salts are hydrochlorides (Gould, 1986) and this trend is reflected in the available salt structures in the Cambridge Structural Database (Allen, 2002): the November 2003 release (Collier, 2004; Jones et al., 2005) showed that of 950 salts in which one component is recorded as being active, an agent or a drug, hydrochlorides are the most common occurring as 55% of the entries, with acetates the next most popular at 17%. It is also evident from the CSD records that there have been very few studies in which crystal structures of multiple salt forms of a single active drug have been reported. Recently (Lewis et al., 2005) the structures of six salts of remacemide have been determined, and the competition between hydrophilic and hydrophobic interactions as drivers for the crystal packings discussed. Our current work seeks to go further using the pharmaceutically active base (1R, 2S)-(−)-ephedrine (I) as a cation from which salts have been prepared from 17 anions, including carboxylates, sulfonates, phosphonates and inorganic species. The CSD already contains determinations for the hemihydrate (Krebs et al., 2001), mono- and dihydrogenphosphates (Hearn et al., 1973; Hearn & Bugg, 1972) and the hydrochloride (Bergin, 1971). The entry for the anhydrous free base (Malone & Parvez, 1978) is incomplete, containing no atomic coordinates: this structure is reported here for the first time. The available hemihydrate structure was solved from powder data at 6 K and so we also report here the results of our single-crystal determination. We have, in addition, redetermined both the hydrochloride and the dihydrogen phosphate since these determinations date from the 1970s. In earlier studies (Leusen et al., 1991, 1992) the structures of five pairs of diastereomeric salts of ephedrine with a cyclic phosphoric acid were reported (Zingg et al., 1988), as well as the structures of the diastereomeric mandelates. These workers were concerned with understanding the structural basis of the chiral resolution process and the relation between solution and crystal structures, respectively, and their studies revealed two conformations of ephedrine in structures based on bilayer packings.

We are concerned with a more general question concerning the process of salt formation. We wanted to explore the relative roles of coulombic and steric factors in directing the packing of molecular salts and, ultimately, to see how crystallographic data might help in providing general guidance for selecting counterions for salt formation. From the previous studies (Leusen et al., 1991, 1992; Zingg et al., 1988) we expected that in our new salts ephedrine would adopt either extended or folded conformations and that, in general, the crystal packings would show polar regions where charged moieties are connected by hydrogen bonds, separated by nonpolar sections comprising phenyl rings and alkyl chains.

2. Experimental

Ephedrine base and the inorganic and organic acids were purchased from Sigma–Aldrich and used as supplied. All crystals were grown at room temperature from equimolar aqueous, methanolic or ethanolic solutions of the base and chosen acid. A glass, 10 ml jacketed vessel connected to a circulating water bath was used in these experiments. This allowed components to be dissolved at 323 K in some experiments so that crystallization could be induced by cooling, while in others the vessel was left open so that evaporative crystallization could occur. In a separate series of experiments solutions of the pure base in water were crystallized to yield a hemihydrate which was dehydrated to an anhydrous form in a desiccator. Single-crystal X-ray diffraction data was collected using a Nonius Kappa CCD diffractometer running routinely at 150 K. Graphite-monochromated Mo Kα radiation (λ = 0.71073 Å) was used. Structure solution was performed either with SIR92 (Altomare et al., 1994) or SHELXS97 (Sheldrick, 1997a), with subsequent refinement achieved using SHELXL97 (Sheldrick, 1997b). The nomenclature used to describe the salt forms of the sulfonic acids is that used widely in the pharmaceutical industry, with besylate representing the counterion benzenesulfonic acid, edisylate (ethanedisulfonic), esylate (ethanesulfonic), mesylate (methanesulfonic) and tosylate (toluenesulfonic), respectively.

3. Results

Table 1 lists the 17 salt systems, together with ephedrine hemihydrate and anhydrous forms, along with summaries of the crystallographic data.¹ We note that for some structures (e.g adipate, hemihydrate, malonate) the ellipsoid plots indicate the presence of unresolved disorder. In the discussion below we describe the details of some of the specific structures, while here we make some general observations.

Table 1
Summary of crystallographic data

R₁ = R[F² > 2σ(F²)], wR₂ = wR(F²), NV = No. of parameters.

Compound	Chemical formula, Mr	Space group, T (K)	Cell parameters (Å, °), V (Å^3), Z	θ max (°), Rint, completeness	R1, wR2, S, Nref, NV, bond precision (Å)	Morphology (fastest growth direction)	Ephedrine dihedral angles (°) and molecular conformation
(1R,2S)-(−)-Ephedrine	C10H15NO, 165.23	P212121, 150	a = 5.6851 (4), b = 7.7047 (5), c = 22.4819 (17), 984.75 (12), 4	27.48, 0.076, 1.00	0.0560, 0.1151, 0.963, 1345, 154, 0.0059	Needle (a axis)	τ^1 = −22.8, τ^2 = −68.0, τ^3 = −166.6, extended
(1R,2S)-(−)-Ephedrine hemihydrate (1:0.5)	2C10H15NO·H2O, 348.48	C2221, 150	a = 7.3639 (4), b = 11.2551 (6), c = 24.1442 (16), 2001.1 (2), 4	25.00, 0.048, 0.99	0.0420, 0.0999, 1.077, 1017, 151, 0.0060	Plate	τ^1 = −31.6, τ^2 = −67.8, τ^3 = −169.3, extended
(1R,2S)-(−)-Ephedrine acetate (1:1)	C10H16NO·C2H3O2, 225.28	P1, 150	a = 5.96420 (10), b = 10.4125 (2), c = 11.7403 (4), α = 108.1750 (10), β = 104.5600 (10), γ = 104.087 (2), 628.08 (3), 2	28.28, 0.062, 0.97	0.0427, 0.1020, 1.033, 3105, 351, 0.0048	Needle (a axis)	τ^1 = 5.6, τ^2 = 60.0, τ^3 = 167.6, extended
(1R,2S)-(−)-Ephedrine adipate (1:1)	C10H16NO·C6H9O4, 311.37	P212121, 150	a = 5.82900 (10), b = 13.5440 (4), c = 21.7000 (7), 1713.17 (8), 4	27.48, 0.028, 0.99	0.0405, 0.0943, 1.034, 2282, 269, 0.0031	Plate	τ^1 = 23.7, τ^2 = 68.1, τ^3 = 168.4, extended
(1R,2S)-(−)-Ephedrine maleate monohydrate (1:1)	C10H16NO·C4H3O4, 299.32	P212121, 150	a = 5.6370 (2), b = 13.4950 (5), c = 20.5250 (5), 1561.36 (9), 4	27.48, 0.052, 0.96	0.0361, 0.0915, 1.052, 2089, 208, 0.0031	Needle (a axis)	τ^1 = −17.2, τ^2 = −54.2, τ^3 = −60.8, folded
(1R,2S)-(−)-Ephedrine hemimalonate (1:0.5)	2C10H16NO·C3H2O4, 434.52	C2, 150	a = 15.1190 (14), b = 5.7840 (7), c = 13.8788 (15), β = 105.765 (7), 1168.0 (2), 2	27.49, 0.061, 0.98	0.0563, 0.1290, 1.063, 1475, 182, 0.0060	Needle (b axis)	τ^1 = 19.8, τ^2 = 69.4, τ^3 = 178.1, extended
(1R,2S)-(−)-Ephedrine glycolate (1:1)	C10H16NO·C2H3O3, 241.28	P21, 150	a = 9.5946 (4), b = 6.0474 (3), c = 10.8255 (5), β = 101.607 (2), 615.28 (5), 2	27.44, 0.035, 0.99	0.0449, 0.0976, 1.081, 1532, 211, 0.0042	Needle (b axis)	τ^1 = −17.2, τ^2 = −63.4, τ^3 = −163.7, extended
(1R,2S)-(−)-Ephedrine L-(−)-malate (1:1)	C10H16NO·C4H5O5, 299.32	P21, 293	a = 6.1312 (6), b = 9.1719 (10), c = 13.7393 (17), β = 100.909 (4), 758.66 (15), 2	27.51, 0.109, 0.93	0.0598, 0.1851, 1.127, 1841, 213, 0.0090	Plate	τ^1 = −16.8, τ^2 = −57.4, τ^3 = −49.1, folded
(1R,2S)-(−)-Ephedrine L-(+)-tartrate monohydrate (1:1)	C10H16NO·C4H5O6, 333.33	P212121, 150	a = 6.6220 (2), b = 7.4620 (3), c = 33.2160 (15), 1641.31 (11), 4	25.67, 0.062, 0.97	0.0399, 0.0874, 1.032, 1844, 263, 0.0049	Plate	τ^1 = −20.8, τ^2 = −50.0, τ^3 = −72.3, folded
(1R,2S)-(−)-Ephedrine L-(+)-hemitartrate trihydrate (1:0.5)	2C10H16NO·C4H4, 534.60	P1, 150	a = 5.9373 (2), b = 7.0594 (2), c = 18.3791 (8), α = 80.2540 (10), β = 88.527 (2), γ = 66.247 (2), 694.14 (4), 1	25.01, 0.081, 0.98	0.0979, 0.2946, 1.311, 2449, 349, 0.0139	Plate	τ^1 = 15.1, τ^2 = 65.2, τ^3 = 173.6, extended
(1R,2S)-(−)-Ephedrine hydrochloride (1:1)	C10H16NOCl, 201.69	P21, 150	a = 7.2557 (3), b = 6.1228 (3), c = 18.3791 (8), β = 102.223 (2), 544.84 (4), 2	27.50, 0.057, 0.98	0.0657, 0.1558, 1.187, 1372, 148, 0.0068	Needle (b axis)	τ^1 = −22.3, τ^2 = −70.7, τ^3 = −168.9, extended
(1R,2S)-(−)-Ephedrine nitrate (1:1)	C10H16NO·NO3, 228.25	P21, 150	a = 5.5309 (4), b = 6.8501 (6), c = 15.6906 (13), β = 97.243 (6), 589.73 (8), 2	27.45, 0.032, 0.87	0.0437, 0.1025, 1.067, 1460, 185, 0.0047	Plate	τ^1 = −23.7, τ^2 = −56.6, τ^3 = −52.6, folded
(1R,2S)-(−)-Ephedrine dihydrogen phosphate (1:1)	C10H16NO·H2PO4, 263.22	C2, 150	a = 14.6992 (10), b = 5.6433 (4), c = 15.2432 (14), β = 97.333 (3), 1254.11 (17), 4	27.36, 0.033, 0.88	0.0510, 0.1194, 1.073, 1569, 173, 0.0053	Needle (b axis)	τ^1 = −21.5, τ^2 = −73.7, τ^3 = 176.4, extended
(1R,2S)-(−)-Ephedrine bisulfate (1:1)	C10H16NO·HSO4, 263.32	C2, 150	a = 30.9967 (17), b = 6.9861 (4), c = 5.6170 (3), β = 93.354 (3), 1214.26 (12), 4	28.93, 0.058, 0.99	0.0735, 0.1253, 1.116, 1739, 173, 0.0057	Needle (c axis)	τ^1 = −25.8, τ^2 = −50.2, τ^3 = −60.2, folded
(1R,2S)-(−)-Ephedrine besylate (1:1)	C10H16NO·C6H5O3S, 323.41	P21, 150	a = 5.7214 (3), b = 20.8336 (11), c = 6.9188 (5), β = 98.409 (2), 815.84 (8), 2	27.47, 0.038, 0.91	0.0554, 0.1127, 1.012, 1919, 260, 0.0061	Plate	τ^1 = −19.7, τ^2 = −58.1, τ^3 = −62.4, folded
(1R, 2S)-(−)-Ephedrine hemiedisylate (1:0.5)	2C10H16NO·C2H4, 520.67	P21, 150	a = 5.71080 (10), b = 34.0651 (7), c = 6.6590 (2), β = 90.09, 1295.43 (5), 2	27.47, 0.032, 0.88	0.0540, 0.1251, 0.984, 3031, 357, 0.0076	Plate	τ^1 = 23.2, τ^2 = 59.1, τ^3 = 53.6, folded
(1R,2S)-(−)-Ephedrine esylate (1:1)	C10H16NO·C2H5O3S, 275.37	P212121, 150	a = 5.4877 (7), b = 11.9057 (17), c = 22.639 (4), 1479.1 (4), 4	28.16, 0.000, 0.86	0.1023, 0.2643, 1.078, 2118, 169, 0.0171	Needle (a axis)	τ^1 = 23.4, τ^2 = 54.4, τ^3 = 59.5, folded
(1R,2S)-(−)-Ephedrine mesylate (1:1)	C10H16NO·CH3O3S, 261.34	C2, 150	a = 14.287 (2), b = 6.1075 (7), c = 14.993 (2), β = 93.211 (6), 1306.2 (3), 4	27.47, 0.029, 0.75	0.0478, 0.1193, 1.101, 1631, 179, 0.0070	Needle (b axis)	τ^1 = −16.3, τ^2 = −65.5, τ^3 = −168.4, extended
(1R,2S)-(−)-Ephedrine p-tosylate (1:1)	C10H16NO·C7H7O3, 337.43	P212121, 150	a = 5.7491 (2), b = 7.1665 (2), c = 42.0343 (9), 1731.85 (9), 4	27.47, 0.018, 0.87	0.0431, 0.0993, 1.040, 2353, 263, 0.0039	Plate	τ^1 = −22.8, τ^2 = −59.3, τ^3 = −55.4, folded

Overall it is clear that the molecular packing in many of these solids reflects the amphiphilic nature of the molecular structure of ephedrine itself, with the almost ubiquitous existence of a molecular bilayer, in which the polar hydroxyl and (protonated) amino functionalities are sandwiched between the nonpolar aromatic moieties. This is as expected from the previously solved salt structures (Leusen et al., 1991, 1992; Zingg et al., 1988) and is indeed seen in other systems which have similar amphiphilic molecular features such as remacemide (Lewis et al., 2005). In the case of the anhydrous solid, the polar functionalities are hydrogen-bonded directly through —OH⋯N— interactions, while in the hemihydrate these interactions are modified by the inclusion of further extensive hydrogen bonding involving the water molecules. In the salts the bilayer expands to incorporate the counterion (and occasionally additional water molecules) through combined coulombic and hydrogen-bonded interactions. In each salt there are two distinct —N—H⋯acceptor distances, one short and one slightly longer. The short distances lie in the range 1.8 (malonate) to 2.2 Å (hydrochloride), while the long distances are in the range 1.9 (dihydrogenphosphate) to 3.0 Å (tartrate trihydrate). In many cases the stability of the bilayer is enhanced through aromatic π–π stacking with distances from the H atom to the closest ring carbon in the range 4.5 (acetate) to 2.8 Å (maleate; Desiraju & Steiner, 1999). Typical π–π stacks taken from four salts are shown in Fig. 1, indicating stacking distances between 3.19 and 2.95 Å. The layers are usually interlinked by face-to-edge or methyl-to-face close contacts with d_{H—π centroid} distances between 3.6 (esylate) and 2.8 Å (dihydrogenphosphate). In the case of the adipate, esylate, besylate and tosylate anions, the existence of additional non-polar interactions between the ions destroys the ephedrine bilayer to yield structures with mixed and alternating layers. In the besylate and tosylate this occurs owing to the possibility of additional anion–anion and cation–cation π–π and face-to-edge interactions; in the adipate, its extended non-polar alkyl chain requires that the bilayer is destroyed and in the case of esylate, the ethyl moiety fits between the phenyl rings of the ephedrine.

Figure 1 π–π stackings of ephedrine from various salt structures. The figures in brackets give the inter-stacking distances in Å. Key: green = ephedrine glycolate (`extended') (3.00, 3.14); blue = ephedrine hydrochloride (`extended') (3.23, 3.10); orange = ephedrine bisulfate (`folded') (3.14, 3.02); red = ephedrine nitrate (`folded') (2.95, 2.92).

The protonated ephedrine molecule adopts one of two conformations in these structures: `folded' or `extended' owing to the three torsions encompassing the chiral C atoms C7 and C8. Only the `folded' conformation includes an intramolecular hydrogen bond. These conformers are shown in Fig. 2(a), and Table 1 incorporates the measured values (achieved using CERIUS<sup>2</sup> (Accelrys Inc., 2003) of the dihedral angles, τ<sup>1</sup>, τ<sup>2</sup> and τ<sup>3</sup>, for ephedrine molecules within each crystal structure. Little variation with respect to the dihedral angles involved in either the `extended' or `folded' conformation can be seen. To demonstrate this, individual units of `extended' and `folded' ephedrine were isolated and overlaid from several salt forms, as seen in Fig. 2(b). This conveys both the similarity in the molecular conformation for units of each conformation and the variation between the two types arising from the torsional flexibility and the intramolecular hydrogen bond. The main difference between the units arises from the variation in τ³ (approximately 100°) from one conformation to the other. Ten structures exhibit the extended form and nine the folded form. In the 12 ephedrine structures examined by Leusen et al. (1991) they noted that nine exhibited the extended conformer but showed that this could not be rationalized by the difference in internal energy since this was insignificant. We have used a MOPAC conformational search to confirm this result and to show that both conformers represent minima in the overall τ², τ³ landscape. Our new structures do not appear to support their notion that the extended conformation is associated with face-to-edge aromatic interactions.

Figure 2 (a) The two conformers of ephedrine. (b) Comparison of ephedrine conformations from selected salt structures. Key: green = ephedrine glycolate (`extended'); blue = ephedrine hydrochloride (`extended'); orange = ephedrine bisulfate (`folded'); red = ephedrine nitrate (`folded').

Overall the crystals studied had either needle or plate morphologies. For those that were needles (pure base, acetate, maleate monohydrate, malonate, glycolate, hydrochloride, dihydrogen phosphate, bisulfate, esylate, mesylate), the needle direction always coincided, as expected, with the direction of the strong coulombic interactions and shortest crystallographic axis. These data are included in Table 1. Although we did not perform a dedicated polymorph search, none were found.

4. Ephedrine neutral base and hemihydrate

Fig. 3 (visualized in MERCURY1.4; Bruno et al., 2002) shows how in the anhydrous neutral base structure, ephedrine molecules are linked along a in hydrogen-bonded chains through alternate —N⋯H—O— interactions between hydroxyl and amino groups, and along b by —C—H⋯ring interactions between methyl groups and phenyl rings on adjacent molecules. The bilayers are then linked along the c axis by T-shaped aromatic —C—H⋯π interactions. The hemihydrate is also based on a bilayer structure, but in this case the inclusion of water molecules into the polar core of the layer enables a different hydrogen-bonding pattern. Our single-crystal structure appears to be essentially similar to that of Krebs et al. (2001) solved from powder data. The bilayers are created by utilizing hydrogen-bonded dimers linked via hydroxyl–water contacts along a and —C—H⋯π interactions along b. These layers are then further linked along c by face-to-edge contacts between neighbouring phenyl rings. In both of these structures the molecule adopts an extended conformation.

Figure 3 Projection of ephedrine free base viewed down b.

5. Inorganic acids

Fig. 4 shows the hydrochloride salt which is essentially the same as in previous structure solutions (Bergin, 1971). This bilayer structure is held along b by coulombic —N—H₂⁺⋯Cl⁻ interactions and along a by chloride–methyl contacts. The bilayers are then stacked along c by face-to-edge contacts between the interdigitated aromatic rings. The dihydrogenphosphate and bisulfate structures (not shown) follow the same pattern, but here the stereochemistry of the anions allows the bilayer to be held by coulombic interactions, hydrogen bonds and π–π stacking. These layers are then interlinked by aromatic face-to-edge contacts. The planarity of the nitrate ion leads to bilayers in which the expected coulombic interaction and hydrogen bonds between the hydroxyl group and nitrate oxygen are supplemented by weaker —C—H⋯O—N— interactions, as seen in Fig. 5. The bilayer is further stabilized by π–π stacking between the aromatic rings and the bilayers are again held together by face-to-edge contacts.

Figure 4 Projection of the hydrochloride salt viewed down a.

Figure 5 Projection of the nitrate salt viewed down a.

6. Carboxylic acids

Structures of the acetate, adipate, maleate, malonate, glycolate, malate and tartrate were solved. In all of these there is, of course, a primary coulombic interaction between the acid anion and the ephedrine cation. Beyond this the actual packing is determined by the nature of the acid involved. The acetate is the simplest comprising (100) bilayers hydrogen bonded as seen in Fig. 6. These layers are interdigitated and held by methyl-to-face and aromatic face-to-edge interactions. In the malonate the dual functionality of the diacid enables the interlinking of bilayers by additional hydrogen bonding along the a axis. In the maleate the increased non-polar nature of the acid, together with the incorporation of water, destroys the bilayer structure totally and creates a three-dimensional hydrogen-bonded network. The acid itself contains an intramolecular hydrogen bond, effectively removing one of its potential hydrogen-bonded functionalities; this is compensated for by the inclusion of water.

Figure 6 Projection of the acetate salt viewed down b.

This trend continues in adipate, which again no longer displays the bilayer features. Here the extended non-polar [—(CH₂)₄—] chain interacts with alternate phenyl rings and the bilayer structure is lost, as seen in Fig. 7. Hydrogen-bonded chains of acid anions run along b. To these chains are bound to ephedrine cations through —C—H⋯aromatic and —O—H⋯O— and —N—H⁺⋯O— interactions. The case of the glycolate represents a further complication, being a hydroxy acid. Fig. 8 illustrates some features of the structure. Here, the dual functionality of the acid allows the creation of sheets, much in the same ways as the inorganic ions. One hydrogen-bonded chain runs along the c axis connecting molecules via carboxylate–amino and hydroxyl–carboxylate interactions. A second identical chain runs along the b axis, creating hydrogen-bonded (100) sheets. These sheets are stacked along the a axis and held by face-to-edge methyl–phenyl and phenyl–phenyl close contacts. The malate structure is a very similar bilayer structure with the hydrogen bonding creating a (001) sheet. These sheets are held by face-to-edge contacts. The hydrated tartrate salts are similar; the structures (not shown) retain a bilayer form with hydrogen-bonded interactions in the core of the bilayer and the bilayers linked by further hydrogen bonding into sheets. Aromatic face-to-edge ring interactions link the sheets along the c axis. In the case of the monohydrate this involves interdigitation of the phenyl rings, while in the trihydrate the bilayer is translated along the c axis.

Figure 7 Projection of the adipate salt viewed down a.

Figure 8 Projection of the glycolate salt viewed down b.

7. Sulfonic acids

The mesylate follows a now familiar pattern in which coulombic and hydrogen-bonded interactions from sulfonate O atoms to amino and hydroxyl groups create an (001) layer, with layers interdigitated and held by aromatic face-to-edge contacts. The addition of one methylene group in the esylate changes the nature of the bilayer, which now exposes (Fig. 9) both phenyl rings of the ephedrine and the methyl group of the sulfonic acid. The bilayers have close methyl-aromatic and face-to-edge aromatic contacts. In the case of the disulfonate edysilate, each anion now bridges two ephedrine cations via hydrogen bonds and coulombic interactions which, together with methyl–aromatic close contacts create (010) sheets interdigitated with face-to-edge interactions. The aromatic nature of the besylate totally destroys the ephedrine bilayer and creates (Fig. 10) a mixed sheet of cations and anions held via coulombic oxygen–amino interactions and oxygen hydroxyl hydrogen bonds. These layers are further stabilized by π–π stacking and methyl-to-face interactions and are held with face-to-edge contacts between phenyl rings of adjacent sulfonic acid anions and ephedrine cations. Finally in the tosylate, the bilayers again comprise both anions and cations. Layers are held together by the usual combination of coulombic, hydrogen bonding and methyl-to-face contacts. Interlayer interactions are face-to-edge on both sides.

Figure 9 Projection of the esylate salt viewed down a.

Figure 10 Projection of the besylate salt viewed down c.

8. Conclusions

This study has provided the structures of 17 salts of the base ephedrine, enabling for the first time the opportunity to compare and contrast the impact of various factors on the crystal packing of a single molecular entity. It is clear that the packings observed incorporate, as expected, both bilayer structures of the ions and the two conformations of the ephedrine ion. It is also evident that the crystal structures of ephedrine base and hydrate contain all the essential structural elements which are then transferred over into the salts, with ions fitting within ephedrine bilayers. The bilayers are typically interconnected through aromatic face-to-edge contacts. With increasing size and hydrophobicity of the anion these layers either incorporate the counterion (besylate and tosylate) or can be destroyed altogether (adipate). In the case of the inorganic salts it is clear that crystal packings are determined by the organic moeties rather than the inorganic ions, even though their additional contribution to the lattice energy is presumably quite large.

The factors determining the ephedrine conformation are not clear. NMR studies of both neutral (Portoghese, 1967) and protonated (Zingg et al., 1988) ephedrine in organic solvents have shown the folded conformer with the intramolecular hydrogen bond to be the favoured form. This suggests that in those instances in which the extended conformer exists, it must be imposed by packing and hydrogen-bonding constraints in the crystalline state. Given the previous calculations (Leusen et al., 1991) showing that the energy barrier between conformers is less than 4.19 kJ mol⁻¹, such a change in conformation could clearly occur during nucleation and crystal growth.

Supporting information

Computing details

For all compounds, data collection: Collect (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997). Data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997) for publication_text, EPHEADIP, EPHEBESY, EPHEEDIS, EPHE, EPHEESYL, EPHEGLYC, EPHEHCL, EPHEHEMI, EPHEMALE, EPHEMALO, EPHEMESY, EPHENITR, EPHEPHOS, EPHEBISU, EPHETART1, EPHETART3, EPHETOSY; HKL DENZO and SCALEPACK (Otwinowski & Minor 1 for EPHEMALA. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997). Program(s) used to refine structure: SHELXL97 (sheldrick, 1997) for publication_text; SHELXL97 (Sheldrick, 1997) for EPHEADIP, EPHEBESY, EPHEEDIS, EPHE, EPHEESYL, EPHEGLYC, EPHEHCL, EPHEHEMI, EPHEMALA, EPHEMALE, EPHEMALO, EPHEMESY, EPHENITR, EPHEPHOS, EPHEBISU, EPHETART1, EPHETART3, EPHETOSY. For all compounds, molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures

(publication_text) (1R, 2S)-(-)-ephedrine acetate

Crystal data

C12H19NO3	Z = 1
Mr = 450.56	F(000) = 244
Triclinic, P1	Dx = 1.191 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9642 (1) Å	Cell parameters from 7676 reflections
b = 10.4125 (2) Å	θ = 0–0°
c = 11.7403 (4) Å	µ = 0.09 mm^−1
α = 108.175 (1)°	T = 150 K
β = 104.560 (1)°	Needle, colourless
γ = 104.087 (2)°	0.3 × 0.05 × 0.05 mm
V = 628.08 (3) Å^3

Data collection

KappaCCD diffractometer	3007 independent reflections
Radiation source: Enraf Nonius FR590	2247 reflections with > 2σ(i)
Graphite monochromator	Rint = 0.062
CCD rotation images, thick slices scans	θmax = 28.3°, θmin = 3.5°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −7→7
Tmin = 0.927, Tmax = 1.051	k = −13→13
11807 measured reflections	l = −15→15

Refinement

Refinement on f^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(fo^2) + (0.0548p)^2 + 0.0180p] where p = (fo^2 + 2fc^2)/3
3007 reflections	(Δ/σ)max < 0.001
351 parameters	Δρmax = 0.18 e Å^−3
3 restraints	Δρmin = −0.22 e Å^−3

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
c01	0.2211 (5)	0.9237 (3)	0.9491 (3)	0.0399 (7)
h01	0.333 (7)	0.890 (4)	0.915 (3)	0.048*
c02	0.2123 (6)	0.9280 (4)	1.0662 (4)	0.0507 (9)
h02	0.3163	0.8947	1.1134	0.061*
c03	0.0502 (6)	0.9815 (3)	1.1138 (3)	0.0461 (8)
h03	0.040 (7)	0.984 (4)	1.191 (4)	0.055*
c04	−0.1086 (6)	1.0281 (3)	1.0413 (3)	0.0437 (8)
h04	−0.230 (7)	1.061 (4)	1.073 (3)	0.052*
c05	−0.1006 (5)	1.0218 (3)	0.9233 (3)	0.0373 (7)
h05	−0.224 (6)	1.046 (4)	0.868 (3)	0.045*
c06	0.0668 (5)	0.9715 (3)	0.8759 (3)	0.0297 (6)
c07	0.0800 (5)	0.9706 (3)	0.7482 (3)	0.0298 (6)
h07	−0.091 (6)	0.922 (3)	0.680 (3)	0.036*
c08	0.1675 (5)	1.1250 (3)	0.7551 (3)	0.0293 (6)
h08	0.057 (6)	1.167 (3)	0.775 (3)	0.035*
c09	0.4253 (5)	1.2176 (3)	0.8537 (3)	0.0400 (7)
h09a	0.5458	1.1849	0.8244	0.06*
h09b	0.4356	1.2097	0.9341	0.06*
h09c	0.4568	1.3164	0.8649	0.06*
c10	0.1881 (6)	1.2533 (3)	0.6078 (3)	0.0360 (7)
h12a	0.155 (6)	1.231 (3)	0.519 (4)	0.043*
h12b	0.355 (6)	1.329 (4)	0.671 (3)	0.043*
h12c	0.058 (6)	1.286 (4)	0.624 (3)	0.043*
c11	0.5376 (5)	0.9674 (3)	0.4752 (3)	0.0290 (6)
c12	0.2796 (5)	0.8617 (3)	0.3923 (3)	0.0383 (7)
h13a	0.2295	0.7963	0.4309	0.057*
h13b	0.2779	0.8084	0.3088	0.057*
h13c	0.1673	0.9134	0.3844	0.057*
c21	0.5902 (5)	1.6417 (3)	1.0878 (3)	0.0353 (7)
h21	0.763 (6)	1.697 (4)	1.151 (3)	0.042*
c22	0.5131 (6)	1.6445 (3)	0.9669 (3)	0.0410 (7)
h22	0.635 (6)	1.705 (4)	0.940 (3)	0.049*
c23	0.2704 (6)	1.5715 (3)	0.8853 (3)	0.0393 (7)
h23	0.212 (6)	1.572 (4)	0.798 (3)	0.047*
c24	0.1053 (6)	1.4912 (4)	0.9229 (3)	0.0403 (7)
h24	−0.066 (7)	1.440 (4)	0.869 (3)	0.048*
c25	0.1832 (5)	1.4871 (4)	1.0432 (3)	0.0387 (7)
h25	0.057 (6)	1.436 (4)	1.070 (3)	0.046*
c26	0.4248 (5)	1.5627 (3)	1.1274 (3)	0.0279 (6)
c27	0.5043 (4)	1.5596 (3)	1.2595 (2)	0.0271 (6)
h27	0.3744	1.5688	1.2953	0.033*
c28	0.5452 (5)	1.4179 (3)	1.2544 (3)	0.0281 (6)
h28	0.383 (6)	1.340 (3)	1.201 (3)	0.034*
c29	0.7507 (5)	1.3977 (3)	1.2056 (3)	0.0374 (7)
h29a	0.9047	1.4716	1.2649	0.056*
h29b	0.7173	1.4038	1.1235	0.056*
h29c	0.7607	1.3047	1.1973	0.056*
c30	0.6195 (6)	1.2859 (3)	1.3991 (3)	0.0361 (7)
h32a	0.637 (6)	1.298 (3)	1.496 (3)	0.043*
h32b	0.472 (7)	1.211 (4)	1.339 (3)	0.043*
h32c	0.762 (7)	1.270 (3)	1.381 (3)	0.043*
c31	0.2496 (4)	0.5727 (3)	0.5515 (2)	0.0248 (6)
c32	0.5108 (5)	0.6702 (3)	0.6366 (3)	0.0423 (8)
h33a	0.5899	0.6206	0.6807	0.063*
h33b	0.5084	0.7556	0.698	0.063*
h33c	0.6006	0.6966	0.5851	0.063*
n01	0.1602 (4)	1.1171 (2)	0.6256 (2)	0.0298 (5)
h10	0.2813	1.0862	0.6088	0.036*
h11	0.0152	1.0505	0.5676	0.036*
n21	0.6061 (4)	1.4229 (2)	1.3886 (2)	0.0258 (5)
h30	0.7524	1.4938	1.4387	0.031*
h31	0.4905	1.4456	1.4192	0.031*
o01	0.2428 (3)	0.9050 (2)	0.7081 (2)	0.0374 (5)
h06	0.1738	0.8171	0.6751	0.056*
o02	0.5679 (3)	1.0778 (2)	0.5663 (2)	0.0370 (5)
o03	0.7149 (3)	0.9349 (2)	0.44695 (19)	0.0384 (5)
o21	0.7290 (3)	1.6704 (2)	1.34584 (18)	0.0349 (5)
h26	0.700 (6)	1.742 (4)	1.369 (3)	0.042*
o22	0.0740 (3)	0.60889 (19)	0.57567 (18)	0.0311 (4)
o23	0.2199 (3)	0.45987 (19)	0.46028 (18)	0.0298 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
c01	0.0325 (17)	0.0408 (17)	0.051 (2)	0.0156 (13)	0.0127 (14)	0.0242 (15)
c02	0.045 (2)	0.056 (2)	0.056 (2)	0.0178 (16)	0.0108 (16)	0.0345 (18)
c03	0.0474 (19)	0.0429 (18)	0.0407 (18)	0.0036 (14)	0.0136 (15)	0.0181 (16)
c04	0.0429 (19)	0.0362 (17)	0.047 (2)	0.0105 (14)	0.0190 (15)	0.0103 (15)
c05	0.0294 (15)	0.0325 (16)	0.0465 (19)	0.0117 (12)	0.0097 (13)	0.0137 (14)
c06	0.0273 (14)	0.0182 (12)	0.0374 (15)	0.0057 (10)	0.0047 (11)	0.0104 (11)
c07	0.0235 (14)	0.0210 (13)	0.0377 (16)	0.0062 (10)	0.0050 (12)	0.0083 (12)
c08	0.0252 (14)	0.0192 (13)	0.0351 (16)	0.0063 (10)	0.0048 (11)	0.0060 (12)
c09	0.0358 (17)	0.0235 (14)	0.0448 (18)	0.0040 (12)	−0.0020 (13)	0.0113 (13)
c10	0.0363 (18)	0.0293 (16)	0.0428 (19)	0.0124 (14)	0.0103 (15)	0.0170 (15)
c11	0.0227 (14)	0.0289 (15)	0.0348 (16)	0.0070 (11)	0.0069 (12)	0.0160 (14)
c12	0.0260 (14)	0.0421 (18)	0.0405 (17)	0.0067 (12)	0.0072 (12)	0.0160 (15)
c21	0.0339 (16)	0.0309 (15)	0.0345 (16)	0.0034 (12)	0.0086 (13)	0.0137 (13)
c22	0.0521 (18)	0.0328 (16)	0.0383 (18)	0.0084 (13)	0.0161 (14)	0.0192 (14)
c23	0.0499 (18)	0.0366 (16)	0.0325 (17)	0.0176 (14)	0.0114 (14)	0.0157 (14)
c24	0.0286 (16)	0.052 (2)	0.0338 (16)	0.0126 (14)	0.0051 (13)	0.0144 (15)
c25	0.0274 (15)	0.0517 (19)	0.0354 (17)	0.0102 (13)	0.0121 (13)	0.0173 (15)
c26	0.0288 (14)	0.0257 (13)	0.0289 (15)	0.0106 (11)	0.0103 (11)	0.0095 (12)
c27	0.0223 (13)	0.0281 (14)	0.0279 (14)	0.0064 (11)	0.0090 (11)	0.0092 (12)
c28	0.0259 (14)	0.0317 (15)	0.0243 (14)	0.0090 (11)	0.0071 (11)	0.0103 (12)
c29	0.0392 (16)	0.0464 (18)	0.0303 (15)	0.0215 (14)	0.0138 (13)	0.0136 (13)
c30	0.0317 (16)	0.0282 (16)	0.0468 (19)	0.0087 (13)	0.0105 (14)	0.0170 (14)
c31	0.0238 (13)	0.0262 (14)	0.0249 (14)	0.0064 (10)	0.0077 (11)	0.0133 (12)
c32	0.0269 (15)	0.0381 (17)	0.0442 (19)	0.0046 (12)	0.0080 (13)	0.0028 (15)
n01	0.0209 (11)	0.0242 (11)	0.0394 (14)	0.0068 (9)	0.0072 (10)	0.0100 (10)
n21	0.0198 (11)	0.0284 (12)	0.0294 (13)	0.0076 (9)	0.0087 (9)	0.0123 (10)
o01	0.0381 (11)	0.0230 (10)	0.0513 (13)	0.0126 (8)	0.0189 (10)	0.0114 (10)
o02	0.0298 (11)	0.0285 (11)	0.0490 (13)	0.0084 (8)	0.0161 (9)	0.0104 (10)
o03	0.0240 (10)	0.0351 (11)	0.0434 (12)	0.0075 (8)	0.0092 (9)	0.0039 (10)
o21	0.0333 (11)	0.0259 (11)	0.0325 (11)	0.0050 (9)	0.0023 (8)	0.0068 (9)
o22	0.0251 (10)	0.0296 (10)	0.0349 (11)	0.0104 (8)	0.0080 (8)	0.0093 (8)
o23	0.0257 (10)	0.0298 (11)	0.0306 (10)	0.0084 (8)	0.0112 (8)	0.0080 (9)

Geometric parameters (Å, º)

c01—c02	1.375 (5)	c22—c23	1.380 (5)
c01—c06	1.389 (4)	c22—h22	1.02 (4)
c01—h01	0.95 (4)	c23—c24	1.383 (5)
c02—c03	1.377 (5)	c23—h23	1.00 (3)
c02—h02	0.93	c24—c25	1.389 (4)
c03—c04	1.390 (5)	c24—h24	0.96 (4)
c03—h03	0.92 (4)	c25—c26	1.385 (4)
c04—c05	1.381 (5)	c25—h25	0.99 (4)
c04—h04	0.98 (4)	c26—c27	1.517 (4)
c05—c06	1.390 (4)	c27—o21	1.411 (3)
c05—h05	0.99 (3)	c27—c28	1.539 (4)
c06—c07	1.518 (4)	c27—h27	0.98
c07—o01	1.408 (3)	c28—n21	1.506 (3)
c07—c08	1.533 (4)	c28—c29	1.509 (4)
c07—h07	1.01 (3)	c28—h28	0.99 (3)
c08—n01	1.486 (4)	c29—h29a	0.96
c08—c09	1.523 (4)	c29—h29b	0.96
c08—h08	0.92 (3)	c29—h29c	0.96
c09—h09a	0.96	c30—n21	1.489 (3)
c09—h09b	0.96	c30—h32a	1.07 (3)
c09—h09c	0.96	c30—h32b	0.94 (4)
c10—n01	1.473 (4)	c30—h32c	0.97 (4)
c10—h12a	0.95 (4)	c31—o23	1.256 (3)
c10—h12b	1.02 (3)	c31—o22	1.263 (3)
c10—h12c	0.96 (3)	c31—c32	1.507 (4)
c11—o02	1.239 (3)	c32—h33a	0.96
c11—o03	1.273 (3)	c32—h33b	0.96
c11—c12	1.510 (4)	c32—h33c	0.96
c12—h13a	0.96	n01—h10	0.9
c12—h13b	0.96	n01—h11	0.9
c12—h13c	0.96	n21—h30	0.9
c21—c22	1.389 (4)	n21—h31	0.9
c21—c26	1.393 (4)	o01—h06	0.82
c21—h21	1.00 (4)	o21—h26	0.78 (4)
c02—c01—c06	121.2 (3)	c22—c23—h23	122 (2)
c02—c01—h01	123 (2)	c24—c23—h23	119 (2)
c06—c01—h01	116 (2)	c23—c24—c25	119.9 (3)
c01—c02—c03	120.4 (3)	c23—c24—h24	121 (2)
c01—c02—h02	119.8	c25—c24—h24	119 (2)
c03—c02—h02	119.8	c26—c25—c24	121.2 (3)
c02—c03—c04	119.5 (3)	c26—c25—h25	120.8 (19)
c02—c03—h03	122 (2)	c24—c25—h25	117.8 (19)
c04—c03—h03	119 (2)	c25—c26—c21	118.4 (3)
c05—c04—c03	119.8 (3)	c25—c26—c27	120.3 (2)
c05—c04—h04	121 (2)	c21—c26—c27	121.3 (2)
c03—c04—h04	119 (2)	o21—c27—c26	113.6 (2)
c04—c05—c06	121.2 (3)	o21—c27—c28	105.4 (2)
c04—c05—h05	119.7 (19)	c26—c27—c28	111.9 (2)
c06—c05—h05	119.0 (19)	o21—c27—h27	108.6
c01—c06—c05	118.0 (3)	c26—c27—h27	108.6
c01—c06—c07	121.5 (3)	c28—c27—h27	108.6
c05—c06—c07	120.5 (2)	n21—c28—c29	110.3 (2)
o01—c07—c06	113.7 (2)	n21—c28—c27	107.1 (2)
o01—c07—c08	106.9 (2)	c29—c28—c27	112.3 (2)
c06—c07—c08	110.6 (2)	n21—c28—h28	107.5 (17)
o01—c07—h07	110.2 (17)	c29—c28—h28	113.4 (17)
c06—c07—h07	109.9 (18)	c27—c28—h28	106.0 (16)
c08—c07—h07	105.1 (18)	c28—c29—h29a	109.5
n01—c08—c09	110.1 (2)	c28—c29—h29b	109.5
n01—c08—c07	108.3 (2)	h29a—c29—h29b	109.5
c09—c08—c07	113.6 (2)	c28—c29—h29c	109.5
n01—c08—h08	107.6 (19)	h29a—c29—h29c	109.5
c09—c08—h08	109 (2)	h29b—c29—h29c	109.5
c07—c08—h08	108 (2)	n21—c30—h32a	107.0 (18)
c08—c09—h09a	109.5	n21—c30—h32b	108 (2)
c08—c09—h09b	109.5	h32a—c30—h32b	111 (3)
h09a—c09—h09b	109.5	n21—c30—h32c	109 (2)
c08—c09—h09c	109.5	h32a—c30—h32c	111 (3)
h09a—c09—h09c	109.5	h32b—c30—h32c	111 (3)
h09b—c09—h09c	109.5	o23—c31—o22	123.9 (2)
n01—c10—h12a	107 (2)	o23—c31—c32	117.7 (2)
n01—c10—h12b	109.2 (18)	o22—c31—c32	118.4 (2)
h12a—c10—h12b	118 (3)	c31—c32—h33a	109.5
n01—c10—h12c	109 (2)	c31—c32—h33b	109.5
h12a—c10—h12c	104 (3)	h33a—c32—h33b	109.5
h12b—c10—h12c	109 (3)	c31—c32—h33c	109.5
o02—c11—o03	123.5 (2)	h33a—c32—h33c	109.5
o02—c11—c12	119.8 (2)	h33b—c32—h33c	109.5
o03—c11—c12	116.6 (3)	c10—n01—c08	115.5 (2)
c11—c12—h13a	109.5	c10—n01—h10	108.4
c11—c12—h13b	109.5	c08—n01—h10	108.4
h13a—c12—h13b	109.5	c10—n01—h11	108.4
c11—c12—h13c	109.5	c08—n01—h11	108.4
h13a—c12—h13c	109.5	h10—n01—h11	107.5
h13b—c12—h13c	109.5	c30—n21—c28	114.5 (2)
c22—c21—c26	120.5 (3)	c30—n21—h30	108.6
c22—c21—h21	122.6 (19)	c28—n21—h30	108.6
c26—c21—h21	117.0 (19)	c30—n21—h31	108.6
c23—c22—c21	120.5 (3)	c28—n21—h31	108.6
c23—c22—h22	120 (2)	h30—n21—h31	107.6
c21—c22—h22	120 (2)	c07—o01—h06	109.5
c22—c23—c24	119.5 (3)	c27—o21—h26	107 (3)
c06—c01—c02—c03	−0.5 (5)	c22—c23—c24—c25	1.5 (5)
c01—c02—c03—c04	1.5 (5)	c23—c24—c25—c26	0.2 (5)
c02—c03—c04—c05	−0.7 (5)	c24—c25—c26—c21	−1.0 (4)
c03—c04—c05—c06	−1.0 (4)	c24—c25—c26—c27	178.5 (3)
c02—c01—c06—c05	−1.1 (4)	c22—c21—c26—c25	0.2 (4)
c02—c01—c06—c07	178.4 (3)	c22—c21—c26—c27	−179.3 (3)
c04—c05—c06—c01	1.9 (4)	c25—c26—c27—o21	−163.3 (2)
c04—c05—c06—c07	−177.7 (3)	c21—c26—c27—o21	16.3 (3)
c01—c06—c07—o01	5.8 (3)	c25—c26—c27—c28	77.5 (3)
c05—c06—c07—o01	−174.7 (2)	c21—c26—c27—c28	−102.9 (3)
c01—c06—c07—c08	−114.5 (3)	o21—c27—c28—n21	59.8 (3)
c05—c06—c07—c08	65.0 (3)	c26—c27—c28—n21	−176.2 (2)
o01—c07—c08—n01	59.6 (3)	o21—c27—c28—c29	−61.3 (3)
c06—c07—c08—n01	−176.1 (2)	c26—c27—c28—c29	62.6 (3)
o01—c07—c08—c09	−63.0 (3)	c09—c08—n01—c10	−67.5 (3)
c06—c07—c08—c09	61.3 (3)	c07—c08—n01—c10	167.7 (2)
c26—c21—c22—c23	1.4 (5)	c29—c28—n21—c30	−65.1 (3)
c21—c22—c23—c24	−2.2 (5)	c27—c28—n21—c30	172.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
n01—h11···o03^i	0.9	1.81	2.705 (3)	173
n01—h11···o02^i	0.9	2.75	3.318 (3)	122
n21—h31···o23^ii	0.9	1.82	2.714 (3)	170
o21—h26···o03^ii	0.78 (4)	1.90 (4)	2.669 (3)	166 (4)
n21—h30···o23^iii	0.9	2.85	3.438 (3)	124

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

(EPHEADIP) (1R, 2S)-(-)-ephedrine adipate

Crystal data

C16H25NO5	F(000) = 672
Mr = 311.37	Dx = 1.207 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2198 reflections
a = 5.8290 (1) Å	θ = 1.0–27.5°
b = 13.5440 (4) Å	µ = 0.09 mm^−1
c = 21.7000 (7) Å	T = 150 K
V = 1713.17 (8) Å^3	Plate, colourless
Z = 4	0.25 × 0.25 × 0.05 mm

Data collection

KappaCCD diffractometer	1808 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	θmax = 27.5°, θmin = 3.2°
Graphite monochromator	h = −7→7
CCD rotation images, thick slices scans	k = −17→17
3874 measured reflections	l = −27→28
2266 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 0.0611P] where P = (Fo^2 + 2Fc^2)/3
2266 reflections	(Δ/σ)max < 0.001
269 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

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
C1	0.8800 (4)	1.13541 (16)	−0.03860 (10)	0.0301 (5)
H1	0.753 (4)	1.1082 (16)	−0.0118 (10)	0.036*
C2	0.8687 (4)	1.23258 (17)	−0.05869 (11)	0.0369 (5)
H2	0.719 (4)	1.2733 (17)	−0.0469 (11)	0.044*
C3	1.0415 (4)	1.27166 (18)	−0.09512 (11)	0.0399 (6)
H3	1.033 (4)	1.341 (2)	−0.1128 (11)	0.048*
C4	1.2274 (4)	1.21354 (17)	−0.11049 (11)	0.0381 (6)
H4	1.353 (5)	1.2426 (19)	−0.1367 (11)	0.046*
C5	1.2402 (4)	1.11630 (16)	−0.09050 (10)	0.0319 (5)
H5	1.380 (4)	1.0754 (17)	−0.0999 (10)	0.038*
C6	1.0656 (3)	1.07666 (15)	−0.05414 (9)	0.0243 (4)
C7	1.0842 (3)	0.97004 (14)	−0.03315 (9)	0.0240 (4)
H7	1.162 (4)	0.9334 (15)	−0.0674 (9)	0.029*
C8	1.2329 (3)	0.96040 (14)	0.02480 (9)	0.0231 (4)
H8	1.382 (4)	0.9931 (15)	0.0167 (9)	0.028*
C9	1.1216 (4)	1.00141 (17)	0.08211 (10)	0.0296 (5)
H9A	1.073 (4)	1.0719 (18)	0.0754 (10)	0.036*
H9B	0.987 (4)	0.9646 (17)	0.0918 (10)	0.036*
H9C	1.216 (4)	0.9979 (17)	0.1151 (10)	0.036*
C10	1.4669 (4)	0.82970 (18)	0.07916 (11)	0.0312 (5)
H12A	1.414 (4)	0.8557 (17)	0.1190 (11)	0.037*
H12B	1.491 (4)	0.7536 (19)	0.0795 (10)	0.037*
H12C	1.605 (4)	0.8666 (17)	0.0657 (10)	0.037*
C11	1.0124 (3)	0.67136 (15)	0.12613 (9)	0.0250 (4)
C12	0.8658 (4)	0.68769 (17)	0.18247 (10)	0.0321 (5)
H13	0.908 (4)	0.6397 (16)	0.2136 (11)	0.039*
H14	0.710 (5)	0.6753 (17)	0.1707 (11)	0.039*
C13	0.8842 (4)	0.79217 (18)	0.20703 (10)	0.0327 (5)
H15	1.035 (5)	0.8071 (17)	0.2204 (11)	0.039*
H16	0.844 (4)	0.8431 (17)	0.1755 (11)	0.039*
C14	0.7242 (5)	0.80945 (19)	0.26106 (11)	0.0473 (6)
H17	0.764	0.764	0.2939	0.057*
H18	0.5684	0.7948	0.2483	0.057*
C15	0.7325 (5)	0.9141 (2)	0.28594 (12)	0.0480 (7)
H19	0.887 (5)	0.936 (2)	0.2940 (13)	0.058*
H20	0.663 (5)	0.9199 (19)	0.3261 (13)	0.058*
C16	0.6204 (5)	0.9895 (2)	0.24503 (13)	0.0630 (9)
N1	1.2860 (3)	0.85283 (12)	0.03256 (8)	0.0233 (4)
H10	1.163 (4)	0.8173 (15)	0.0427 (10)	0.028*
H11	1.339 (4)	0.8239 (15)	−0.0079 (10)	0.028*
O1	0.8699 (2)	0.92552 (11)	−0.01902 (7)	0.0302 (4)
H6	0.804 (4)	0.9125 (17)	−0.0549 (11)	0.036*
O2	0.9614 (2)	0.71905 (10)	0.07795 (6)	0.0263 (3)
O3	1.1767 (3)	0.61184 (12)	0.12894 (7)	0.0435 (5)
O4	0.5197 (5)	0.97026 (19)	0.19809 (12)	0.1134 (11)
O5	0.6364 (4)	1.08406 (16)	0.26288 (10)	0.0671 (6)
H21	0.703 (6)	1.086 (2)	0.2997 (16)	0.08*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0286 (10)	0.0328 (12)	0.0289 (11)	0.0020 (10)	0.0000 (9)	0.0010 (9)
C2	0.0382 (12)	0.0345 (13)	0.0380 (12)	0.0086 (11)	−0.0047 (11)	−0.0016 (10)
C3	0.0515 (14)	0.0289 (12)	0.0392 (13)	−0.0018 (12)	−0.0120 (12)	0.0054 (11)
C4	0.0408 (12)	0.0374 (13)	0.0360 (12)	−0.0084 (11)	0.0002 (11)	0.0106 (10)
C5	0.0302 (11)	0.0354 (12)	0.0301 (11)	0.0002 (10)	0.0005 (10)	0.0039 (10)
C6	0.0248 (9)	0.0270 (11)	0.0210 (9)	−0.0017 (9)	−0.0035 (8)	0.0000 (8)
C7	0.0242 (9)	0.0257 (10)	0.0220 (10)	−0.0010 (9)	−0.0015 (8)	0.0004 (9)
C8	0.0243 (9)	0.0200 (10)	0.0251 (10)	−0.0028 (9)	−0.0012 (8)	−0.0006 (8)
C9	0.0368 (11)	0.0276 (12)	0.0243 (11)	0.0016 (10)	−0.0032 (10)	−0.0023 (9)
C10	0.0297 (10)	0.0334 (13)	0.0304 (12)	0.0030 (10)	−0.0075 (10)	0.0036 (10)
C11	0.0281 (10)	0.0242 (10)	0.0225 (10)	−0.0019 (9)	0.0024 (9)	0.0006 (9)
C12	0.0380 (12)	0.0335 (12)	0.0249 (11)	0.0033 (11)	0.0071 (10)	0.0043 (10)
C13	0.0332 (11)	0.0406 (13)	0.0243 (11)	0.0009 (11)	0.0034 (9)	−0.0044 (10)
C14	0.0522 (14)	0.0573 (16)	0.0324 (12)	−0.0031 (13)	0.0106 (12)	−0.0153 (12)
C15	0.0490 (15)	0.0630 (17)	0.0320 (12)	0.0028 (15)	0.0022 (12)	−0.0237 (13)
C16	0.0529 (14)	0.074 (2)	0.0616 (17)	0.0283 (16)	−0.0257 (15)	−0.0455 (16)
N1	0.0236 (8)	0.0235 (9)	0.0228 (9)	−0.0011 (8)	−0.0017 (7)	0.0008 (7)
O1	0.0281 (7)	0.0358 (8)	0.0268 (8)	−0.0093 (7)	−0.0051 (6)	0.0022 (7)
O2	0.0294 (7)	0.0273 (8)	0.0224 (7)	−0.0006 (6)	0.0004 (6)	0.0033 (6)
O3	0.0473 (10)	0.0525 (10)	0.0308 (8)	0.0246 (9)	0.0111 (7)	0.0146 (7)
O4	0.133 (2)	0.1035 (18)	0.1035 (17)	0.0730 (17)	−0.0912 (18)	−0.0781 (15)
O5	0.0744 (13)	0.0663 (12)	0.0605 (12)	0.0330 (12)	−0.0322 (11)	−0.0371 (11)

Geometric parameters (Å, º)

C1—C6	1.385 (3)	C10—H12B	1.04 (2)
C1—C2	1.388 (3)	C10—H12C	0.99 (3)
C1—H1	1.01 (2)	C11—O3	1.253 (2)
C2—C3	1.386 (4)	C11—O2	1.264 (2)
C2—H2	1.06 (3)	C11—C12	1.508 (3)
C3—C4	1.380 (3)	C12—C13	1.516 (3)
C3—H3	1.02 (3)	C12—H13	0.97 (2)
C4—C5	1.389 (3)	C12—H14	0.96 (3)
C4—H4	1.01 (3)	C13—C14	1.517 (3)
C5—C6	1.395 (3)	C13—H15	0.95 (3)
C5—H5	1.01 (2)	C13—H16	1.00 (2)
C6—C7	1.518 (3)	C14—C15	1.517 (4)
C7—O1	1.420 (2)	C14—H17	0.97
C7—C8	1.533 (3)	C14—H18	0.97
C7—H7	1.00 (2)	C15—C16	1.503 (4)
C8—N1	1.499 (2)	C15—H19	0.96 (3)
C8—C9	1.509 (3)	C15—H20	0.96 (3)
C8—H8	0.99 (2)	C16—O4	1.204 (3)
C9—H9A	1.01 (2)	C16—O5	1.341 (3)
C9—H9B	0.95 (2)	N1—H10	0.89 (2)
C9—H9C	0.90 (2)	N1—H11	1.01 (2)
C10—N1	1.494 (3)	O1—H6	0.89 (3)
C10—H12A	0.98 (2)	O5—H21	0.89 (3)
C6—C1—C2	120.4 (2)	H12A—C10—H12C	109.4 (19)
C6—C1—H1	120.1 (13)	H12B—C10—H12C	112.9 (18)
C2—C1—H1	119.5 (13)	O3—C11—O2	123.26 (18)
C3—C2—C1	120.4 (2)	O3—C11—C12	119.21 (18)
C3—C2—H2	122.3 (13)	O2—C11—C12	117.53 (18)
C1—C2—H2	117.1 (13)	C11—C12—C13	112.45 (18)
C4—C3—C2	119.4 (2)	C11—C12—H13	108.9 (14)
C4—C3—H3	118.5 (15)	C13—C12—H13	111.3 (13)
C2—C3—H3	122.1 (15)	C11—C12—H14	107.2 (14)
C3—C4—C5	120.5 (2)	C13—C12—H14	108.9 (14)
C3—C4—H4	119.0 (14)	H13—C12—H14	107.8 (19)
C5—C4—H4	120.5 (15)	C12—C13—C14	111.9 (2)
C4—C5—C6	120.2 (2)	C12—C13—H15	111.9 (14)
C4—C5—H5	120.2 (13)	C14—C13—H15	107.6 (14)
C6—C5—H5	119.5 (13)	C12—C13—H16	112.7 (13)
C1—C6—C5	119.10 (19)	C14—C13—H16	106.1 (14)
C1—C6—C7	121.97 (18)	H15—C13—H16	106 (2)
C5—C6—C7	118.92 (18)	C13—C14—C15	113.6 (2)
O1—C7—C6	113.93 (16)	C13—C14—H17	108.9
O1—C7—C8	106.50 (15)	C15—C14—H17	108.9
C6—C7—C8	111.57 (16)	C13—C14—H18	108.9
O1—C7—H7	110.3 (12)	C15—C14—H18	108.9
C6—C7—H7	106.3 (12)	H17—C14—H18	107.7
C8—C7—H7	108.1 (12)	C16—C15—C14	114.3 (2)
N1—C8—C9	110.74 (17)	C16—C15—H19	107.8 (17)
N1—C8—C7	106.96 (15)	C14—C15—H19	112.4 (16)
C9—C8—C7	113.70 (17)	C16—C15—H20	107.2 (17)
N1—C8—H8	105.9 (12)	C14—C15—H20	112.6 (16)
C9—C8—H8	111.0 (12)	H19—C15—H20	102 (2)
C7—C8—H8	108.2 (12)	O4—C16—O5	119.0 (3)
C8—C9—H9A	110.5 (12)	O4—C16—C15	124.4 (3)
C8—C9—H9B	110.0 (14)	O5—C16—C15	116.6 (2)
H9A—C9—H9B	107.3 (18)	C10—N1—C8	115.19 (17)
C8—C9—H9C	111.8 (15)	C10—N1—H10	106.7 (14)
H9A—C9—H9C	109.7 (19)	C8—N1—H10	112.7 (14)
H9B—C9—H9C	107.4 (19)	C10—N1—H11	106.9 (12)
N1—C10—H12A	107.4 (14)	C8—N1—H11	110.0 (12)
N1—C10—H12B	108.0 (13)	H10—N1—H11	104.7 (18)
H12A—C10—H12B	113.0 (19)	C7—O1—H6	106.2 (15)
N1—C10—H12C	105.6 (13)	C16—O5—H21	109 (2)
C6—C1—C2—C3	0.8 (3)	C6—C7—C8—N1	−166.74 (16)
C1—C2—C3—C4	−1.1 (4)	O1—C7—C8—C9	−54.2 (2)
C2—C3—C4—C5	1.0 (4)	C6—C7—C8—C9	70.7 (2)
C3—C4—C5—C6	−0.6 (3)	O3—C11—C12—C13	115.1 (2)
C2—C1—C6—C5	−0.3 (3)	O2—C11—C12—C13	−65.0 (3)
C2—C1—C6—C7	−179.93 (19)	C11—C12—C13—C14	176.2 (2)
C4—C5—C6—C1	0.3 (3)	C12—C13—C14—C15	−178.4 (2)
C4—C5—C6—C7	179.85 (18)	C13—C14—C15—C16	72.7 (3)
C1—C6—C7—O1	23.6 (3)	C14—C15—C16—O4	4.2 (4)
C5—C6—C7—O1	−155.96 (18)	C14—C15—C16—O5	−175.7 (3)
C1—C6—C7—C8	−97.0 (2)	C9—C8—N1—C10	−67.2 (2)
C5—C6—C7—C8	83.4 (2)	C7—C8—N1—C10	168.43 (17)
O1—C7—C8—N1	68.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H6···O3^i	0.89 (3)	1.80 (3)	2.686 (2)	178 (2)
N1—H11···O2^ii	1.01 (2)	1.78 (2)	2.783 (2)	173.6 (19)
O5—H21···O3^iii	0.89 (3)	1.73 (3)	2.615 (2)	170 (3)

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

(EPHEBESY) (1R, 2S)-(-)-ephedrine besylate

Crystal data

C16H20O4S	F(000) = 344
Mr = 323.4	Dx = 1.316 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7649 reflections
a = 5.7214 (3) Å	θ = 1.0–27.5°
b = 20.8336 (11) Å	µ = 0.22 mm^−1
c = 6.9188 (5) Å	T = 150 K
β = 98.409 (2)°	Plate, brown
V = 815.84 (8) Å^3	0.25 × 0.25 × 0.05 mm
Z = 2

Data collection

KappaCCD diffractometer	3395 independent reflections
Radiation source: Enraf Nonius FR590	2159 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −7→7
Tmin = 0.984, Tmax = 1.024	k = −24→26
5520 measured reflections	l = −7→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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0302P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
3395 reflections	Δρmax = 0.27 e Å^−3
260 parameters	Δρmin = −0.42 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (11)

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
C1	1.3882 (8)	0.85924 (19)	0.6682 (6)	0.0302 (10)
H1	1.232 (9)	0.8493 (18)	0.590 (6)	0.036*
C2	1.4381 (9)	0.9179 (2)	0.7637 (7)	0.0354 (11)
H2	1.306 (8)	0.9518 (19)	0.736 (6)	0.042*
C3	1.6630 (9)	0.9295 (2)	0.8638 (6)	0.0348 (11)
H3	1.712 (8)	0.967 (2)	0.923 (6)	0.042*
C4	1.8332 (8)	0.8831 (2)	0.8709 (7)	0.0355 (11)
H4	1.983 (8)	0.892 (2)	0.935 (6)	0.043*
C5	1.7846 (8)	0.8246 (2)	0.7771 (6)	0.0292 (10)
H5	1.911 (7)	0.7929 (19)	0.784 (6)	0.035*
C6	1.5624 (7)	0.81220 (17)	0.6745 (5)	0.0208 (9)
C7	1.5112 (8)	0.74808 (19)	0.5743 (6)	0.0265 (10)
H7	1.598 (7)	0.717 (2)	0.648 (6)	0.032*
C8	1.6069 (8)	0.74590 (18)	0.3781 (6)	0.0257 (9)
H8	1.778 (7)	0.7451 (17)	0.408 (6)	0.031*
C9	1.4924 (11)	0.7943 (2)	0.2315 (7)	0.0358 (12)
H9A	1.539 (8)	0.7903 (19)	0.110 (7)	0.043*
H9B	1.524 (9)	0.835 (2)	0.270 (7)	0.043*
H9C	1.313 (9)	0.785 (2)	0.216 (6)	0.043*
C10	1.6836 (9)	0.6260 (2)	0.4045 (7)	0.0338 (12)
H12A	1.628 (7)	0.6208 (19)	0.524 (7)	0.041*
H12B	1.851 (8)	0.631 (2)	0.421 (6)	0.041*
H12C	1.633 (8)	0.584 (2)	0.321 (7)	0.041*
C11	2.2319 (8)	0.5644 (2)	0.7256 (6)	0.0300 (11)
H13	2.344 (8)	0.6002 (19)	0.741 (6)	0.036*
C12	2.2484 (8)	0.5099 (2)	0.6154 (7)	0.0377 (12)
H14	2.393 (8)	0.504 (2)	0.543 (6)	0.045*
C13	2.0794 (8)	0.4618 (2)	0.6064 (7)	0.0358 (11)
H15	2.079 (7)	0.426 (2)	0.524 (6)	0.043*
C14	1.8907 (9)	0.4692 (2)	0.7111 (7)	0.0357 (11)
H16	1.779 (8)	0.431 (2)	0.713 (6)	0.043*
C15	1.8736 (8)	0.52318 (19)	0.8223 (6)	0.0291 (10)
H17	1.749 (8)	0.5324 (19)	0.901 (7)	0.035*
C16	2.0422 (7)	0.57102 (17)	0.8286 (6)	0.0229 (9)
O1	1.2687 (5)	0.73278 (13)	0.5334 (4)	0.0291 (7)
H6	1.2258	0.7164	0.6301	0.044*
O2	2.1234 (5)	0.62436 (12)	1.1704 (4)	0.0303 (7)
O3	2.1531 (5)	0.69075 (12)	0.8878 (4)	0.0330 (7)
O4	1.7664 (5)	0.65500 (12)	0.9529 (4)	0.0293 (7)
S1	2.01984 (17)	0.64093 (4)	0.97080 (13)	0.0249 (2)
N1	1.5633 (7)	0.68021 (15)	0.2902 (5)	0.0232 (8)
H10	1.620 (7)	0.6774 (18)	0.184 (6)	0.028*
H11	1.397 (8)	0.6682 (16)	0.275 (5)	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.032 (3)	0.032 (2)	0.026 (2)	−0.003 (2)	0.004 (2)	0.0010 (18)
C2	0.041 (3)	0.032 (2)	0.034 (3)	0.001 (2)	0.007 (2)	0.001 (2)
C3	0.043 (3)	0.034 (2)	0.029 (3)	−0.012 (2)	0.013 (2)	−0.008 (2)
C4	0.028 (3)	0.048 (3)	0.030 (3)	−0.009 (2)	0.002 (2)	−0.010 (2)
C5	0.029 (3)	0.034 (2)	0.026 (2)	0.003 (2)	0.006 (2)	−0.0031 (19)
C6	0.025 (2)	0.025 (2)	0.013 (2)	−0.0022 (17)	0.0085 (18)	−0.0011 (16)
C7	0.025 (3)	0.032 (2)	0.024 (3)	0.0023 (19)	0.009 (2)	0.0005 (18)
C8	0.027 (2)	0.029 (2)	0.022 (2)	−0.0024 (19)	0.0053 (19)	−0.0021 (17)
C9	0.057 (3)	0.034 (3)	0.020 (3)	−0.002 (2)	0.014 (2)	0.002 (2)
C10	0.038 (3)	0.041 (3)	0.026 (2)	0.008 (2)	0.015 (2)	0.005 (2)
C11	0.029 (3)	0.033 (2)	0.030 (3)	0.0004 (19)	0.013 (2)	−0.0039 (19)
C12	0.035 (3)	0.041 (3)	0.039 (3)	0.005 (2)	0.011 (2)	−0.009 (2)
C13	0.039 (3)	0.034 (3)	0.032 (3)	0.003 (2)	−0.002 (2)	−0.011 (2)
C14	0.034 (3)	0.032 (2)	0.037 (3)	−0.003 (2)	−0.009 (2)	0.002 (2)
C15	0.025 (3)	0.035 (2)	0.026 (3)	−0.001 (2)	0.001 (2)	0.0011 (19)
C16	0.023 (2)	0.027 (2)	0.019 (2)	0.0017 (17)	0.0039 (19)	0.0027 (16)
O1	0.0272 (18)	0.0397 (17)	0.0223 (16)	−0.0100 (13)	0.0097 (13)	−0.0014 (13)
O2	0.0269 (17)	0.0444 (18)	0.0192 (15)	−0.0031 (12)	0.0023 (13)	−0.0004 (11)
O3	0.0404 (19)	0.0281 (15)	0.0350 (18)	−0.0045 (13)	0.0207 (15)	0.0024 (13)
O4	0.0209 (16)	0.0428 (19)	0.0249 (15)	0.0065 (12)	0.0055 (12)	−0.0032 (12)
S1	0.0257 (6)	0.0300 (5)	0.0204 (5)	−0.0006 (5)	0.0083 (4)	0.0003 (5)
N1	0.022 (2)	0.0298 (19)	0.0190 (19)	−0.0037 (15)	0.0072 (17)	−0.0014 (15)

Geometric parameters (Å, º)

C1—C6	1.394 (6)	C10—H12A	0.94 (5)
C1—C2	1.398 (6)	C10—H12B	0.96 (4)
C1—H1	1.00 (5)	C10—H12C	1.06 (4)
C2—C3	1.390 (6)	C11—C12	1.379 (6)
C2—H2	1.03 (4)	C11—C16	1.390 (6)
C3—C4	1.368 (6)	C11—H13	0.98 (4)
C3—H3	0.91 (4)	C12—C13	1.386 (6)
C4—C5	1.389 (6)	C12—H14	1.04 (4)
C4—H4	0.93 (5)	C13—C14	1.394 (7)
C5—C6	1.387 (5)	C13—H15	0.94 (4)
C5—H5	0.97 (4)	C14—C15	1.375 (6)
C6—C7	1.514 (5)	C14—H16	1.02 (4)
C7—O1	1.411 (5)	C15—C16	1.384 (6)
C7—C8	1.537 (5)	C15—H17	0.98 (5)
C7—H7	0.92 (4)	C16—S1	1.773 (4)
C8—N1	1.504 (5)	O1—H6	0.82
C8—C9	1.510 (6)	O2—S1	1.462 (3)
C8—H8	0.97 (4)	O3—S1	1.455 (3)
C9—H9A	0.92 (5)	O4—S1	1.467 (3)
C9—H9B	0.91 (5)	N1—H10	0.85 (4)
C9—H9C	1.03 (5)	N1—H11	0.97 (4)
C10—N1	1.488 (5)
C6—C1—C2	120.3 (4)	N1—C10—H12B	111 (3)
C6—C1—H1	117 (2)	H12A—C10—H12B	112 (3)
C2—C1—H1	123 (2)	N1—C10—H12C	105 (3)
C3—C2—C1	119.9 (4)	H12A—C10—H12C	107 (4)
C3—C2—H2	125 (2)	H12B—C10—H12C	111 (4)
C1—C2—H2	115 (2)	C12—C11—C16	119.1 (4)
C4—C3—C2	119.8 (4)	C12—C11—H13	126 (2)
C4—C3—H3	115 (3)	C16—C11—H13	115 (2)
C2—C3—H3	125 (3)	C11—C12—C13	121.1 (4)
C3—C4—C5	120.7 (4)	C11—C12—H14	119 (3)
C3—C4—H4	118 (3)	C13—C12—H14	120 (3)
C5—C4—H4	121 (3)	C12—C13—C14	119.1 (4)
C6—C5—C4	120.6 (4)	C12—C13—H15	123 (3)
C6—C5—H5	121 (2)	C14—C13—H15	118 (3)
C4—C5—H5	118 (2)	C15—C14—C13	120.3 (4)
C5—C6—C1	118.9 (4)	C15—C14—H16	122 (3)
C5—C6—C7	120.0 (4)	C13—C14—H16	117 (3)
C1—C6—C7	121.1 (4)	C14—C15—C16	120.0 (4)
O1—C7—C6	114.2 (3)	C14—C15—H17	126 (2)
O1—C7—C8	106.4 (3)	C16—C15—H17	114 (2)
C6—C7—C8	111.1 (3)	C15—C16—C11	120.4 (4)
O1—C7—H7	113 (3)	C15—C16—S1	120.2 (3)
C6—C7—H7	109 (3)	C11—C16—S1	119.4 (3)
C8—C7—H7	103 (3)	C7—O1—H6	109.5
N1—C8—C9	107.9 (3)	O3—S1—O2	112.21 (16)
N1—C8—C7	108.9 (3)	O3—S1—O4	113.13 (16)
C9—C8—C7	113.4 (4)	O2—S1—O4	112.69 (16)
N1—C8—H8	100 (2)	O3—S1—C16	106.40 (17)
C9—C8—H8	119 (2)	O2—S1—C16	106.15 (17)
C7—C8—H8	107 (2)	O4—S1—C16	105.55 (17)
C8—C9—H9A	113 (3)	C10—N1—C8	116.1 (3)
C8—C9—H9B	113 (3)	C10—N1—H10	102 (3)
H9A—C9—H9B	106 (4)	C8—N1—H10	111 (3)
C8—C9—H9C	105 (2)	C10—N1—H11	103 (2)
H9A—C9—H9C	107 (4)	C8—N1—H11	112 (2)
H9B—C9—H9C	112 (4)	H10—N1—H11	112 (4)
N1—C10—H12A	112 (2)
C6—C1—C2—C3	0.6 (6)	C16—C11—C12—C13	−0.1 (7)
C1—C2—C3—C4	−1.0 (7)	C11—C12—C13—C14	−0.1 (7)
C2—C3—C4—C5	0.7 (7)	C12—C13—C14—C15	−0.3 (7)
C3—C4—C5—C6	0.0 (7)	C13—C14—C15—C16	0.9 (6)
C4—C5—C6—C1	−0.4 (6)	C14—C15—C16—C11	−1.1 (6)
C4—C5—C6—C7	−179.5 (4)	C14—C15—C16—S1	179.7 (3)
C2—C1—C6—C5	0.1 (6)	C12—C11—C16—C15	0.7 (6)
C2—C1—C6—C7	179.2 (4)	C12—C11—C16—S1	179.9 (3)
C5—C6—C7—O1	159.7 (3)	C15—C16—S1—O3	−156.9 (3)
C1—C6—C7—O1	−19.4 (5)	C11—C16—S1—O3	23.9 (4)
C5—C6—C7—C8	−79.9 (5)	C15—C16—S1—O2	83.4 (4)
C1—C6—C7—C8	101.0 (4)	C11—C16—S1—O2	−95.8 (3)
O1—C7—C8—N1	−58.2 (4)	C15—C16—S1—O4	−36.5 (4)
C6—C7—C8—N1	176.9 (3)	C11—C16—S1—O4	144.3 (3)
O1—C7—C8—C9	62.0 (4)	C9—C8—N1—C10	174.0 (4)
C6—C7—C8—C9	−62.9 (5)	C7—C8—N1—C10	−62.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O4^i	0.85 (4)	1.97 (4)	2.804 (4)	170 (4)
N1—H10···S1^i	0.85 (4)	3.00 (4)	3.750 (4)	149 (3)
N1—H11···O2^ii	0.97 (4)	1.87 (4)	2.787 (5)	156 (3)
N1—H11···S1^ii	0.97 (4)	2.84 (4)	3.635 (4)	139 (3)
O1—H6···O3^iii	0.82	1.96	2.773 (4)	169

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

(EPHEEDIS) (1R, 2S)-(-)-ephedrine edisylate

Crystal data

C22H36N2O8S2	F(000) = 556
Mr = 520.65	Dx = 1.335 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 13259 reflections
a = 5.7108 (1) Å	θ = 1.0–27.5°
b = 34.0651 (7) Å	µ = 0.25 mm^−1
c = 6.6590 (2) Å	T = 150 K
β = 90.09°	Plate, white
V = 1295.43 (5) Å^3	0.35 × 0.35 × 0.05 mm
Z = 2

Data collection

KappaCCD diffractometer	5249 independent reflections
Radiation source: Enraf Nonius FR590	3134 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −4→7
Tmin = 0.979, Tmax = 1.027	k = −41→44
10886 measured reflections	l = −7→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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0481P)^2 + 0.2649P] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
5249 reflections	Δρmax = 0.31 e Å^−3
357 parameters	Δρmin = −0.37 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (11)

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
C01	0.7038 (8)	0.90658 (15)	0.9014 (7)	0.0391 (12)
H01	0.5944	0.9267	0.8921	0.047*
C02	0.6496 (11)	0.86970 (17)	0.8240 (8)	0.0502 (15)
H02	0.499 (9)	0.8631 (15)	0.767 (7)	0.055 (16)*
C03	0.8089 (12)	0.84027 (19)	0.8410 (9)	0.0527 (17)
H03	0.767 (8)	0.8138 (14)	0.782 (7)	0.049 (14)*
C04	1.0209 (11)	0.84649 (16)	0.9342 (9)	0.0458 (15)
H04	1.126 (8)	0.8260 (14)	0.950 (6)	0.031 (13)*
C05	1.0740 (10)	0.88305 (15)	1.0101 (8)	0.0389 (13)
H05	1.213 (7)	0.8836 (12)	1.064 (6)	0.019 (12)*
C06	0.9182 (8)	0.91369 (15)	0.9922 (7)	0.0288 (12)
C07	0.9738 (8)	0.95497 (15)	1.0672 (7)	0.0311 (12)
H7	0.905 (7)	0.9785 (13)	0.970 (6)	0.036 (13)*
C08	0.8671 (8)	0.96273 (14)	1.2739 (7)	0.0320 (12)
H08	0.6961	0.9622	1.2621	0.038*
C09	0.9419 (12)	0.93356 (18)	1.4325 (8)	0.0589 (18)
H09A	1.1097	0.9321	1.4362	0.088*
H09B	0.8786	0.9082	1.401	0.088*
H09C	0.8849	0.9419	1.5612	0.088*
C10	0.8845 (8)	1.03619 (14)	1.2058 (7)	0.0398 (13)
H12A	0.9705	1.0333	1.083	0.06*
H12B	0.926	1.0606	1.2685	0.06*
H12C	0.7197	1.036	1.1773	0.06*
C11	1.1361 (9)	1.08813 (16)	0.7161 (8)	0.0294 (12)
H13	1.012 (9)	1.0713 (15)	0.760 (7)	0.047 (14)*
H14	1.137 (7)	1.0936 (11)	0.578 (6)	0.015 (10)*
C12	1.3726 (8)	1.07241 (15)	0.7801 (7)	0.0277 (12)
H15	1.3725	1.0679	0.924	0.033*
H16	1.4924	1.0918	0.7507	0.033*
C21	1.6242 (8)	0.76002 (15)	0.4064 (7)	0.0392 (12)
H21	1.7384	0.7406	0.3982	0.047*
C22	1.6691 (11)	0.79639 (17)	0.3293 (8)	0.0468 (14)
H22	1.833 (8)	0.8019 (13)	0.274 (6)	0.039 (13)*
C23	1.5031 (11)	0.82548 (17)	0.3433 (8)	0.0514 (16)
H23	1.5331	0.8502	0.2898	0.062*
C24	1.2959 (12)	0.81820 (17)	0.4348 (9)	0.0498 (16)
H24	1.183 (9)	0.8370 (15)	0.441 (7)	0.039 (14)*
C25	1.2466 (8)	0.78152 (14)	0.5112 (7)	0.0379 (12)
H25	1.103	0.7769	0.5725	0.045*
C26	1.4099 (8)	0.75136 (15)	0.4973 (7)	0.0287 (12)
C27	1.3662 (8)	0.70974 (15)	0.5746 (7)	0.0289 (12)
H27	1.454 (6)	0.6919 (12)	0.494 (5)	0.011 (11)*
C28	1.4679 (9)	0.70392 (14)	0.7834 (7)	0.0311 (12)
H28	1.619 (7)	0.7051 (12)	0.776 (6)	0.020 (12)*
C29	1.3654 (11)	0.73094 (18)	0.9421 (7)	0.0580 (18)
H29A	1.1984	0.7278	0.9454	0.087*
H29B	1.4032	0.7577	0.91	0.087*
H29C	1.4299	0.7244	1.071	0.087*
C30	1.5080 (9)	0.63087 (15)	0.7106 (7)	0.0407 (12)
H32A	1.4063	0.6297	0.5958	0.061*
H32B	1.5052	0.6061	0.7794	0.061*
H32C	1.6648	0.6365	0.6676	0.061*
N01	0.9421 (6)	1.00332 (11)	1.3427 (6)	0.0304 (10)
H10	0.8751	1.0081	1.4625	0.036*
H11	1.0982	1.0031	1.3618	0.036*
N21	1.4267 (6)	0.66234 (11)	0.8487 (5)	0.0304 (10)
H30	1.4978	0.6588	0.9681	0.036*
H31	1.272	0.6592	0.8683	0.036*
O02	0.8585 (5)	1.14831 (10)	0.7290 (5)	0.0396 (9)
O03	1.2702 (5)	1.15841 (9)	0.8096 (5)	0.0343 (8)
O04	1.0147 (6)	1.12468 (10)	1.0438 (4)	0.0364 (9)
O05	1.4018 (5)	1.03526 (10)	0.4410 (4)	0.0357 (8)
O06	1.6839 (5)	1.01977 (10)	0.7020 (4)	0.0350 (8)
O07	1.2764 (6)	0.99872 (10)	0.7302 (5)	0.0414 (9)
O21	1.1214 (5)	0.70113 (10)	0.5869 (5)	0.0368 (8)
H26	1.0846	0.6863	0.4952	0.055*
S1	1.06486 (19)	1.13367 (3)	0.83440 (17)	0.0284 (3)
S2	1.43963 (19)	1.02792 (3)	0.65424 (17)	0.0281 (3)
O01	1.2197 (5)	0.96210 (9)	1.0871 (5)	0.0377 (8)
H06	1.2822	0.9432	1.141	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C01	0.033 (3)	0.047 (3)	0.037 (3)	−0.001 (2)	0.006 (2)	−0.007 (2)
C02	0.041 (3)	0.063 (4)	0.047 (3)	−0.014 (3)	0.009 (3)	−0.022 (3)
C03	0.059 (4)	0.046 (4)	0.053 (4)	−0.016 (4)	0.017 (3)	−0.017 (3)
C04	0.057 (4)	0.028 (3)	0.052 (4)	0.005 (3)	0.009 (3)	−0.004 (3)
C05	0.035 (3)	0.042 (3)	0.040 (3)	0.003 (3)	0.000 (3)	0.003 (3)
C06	0.034 (3)	0.030 (3)	0.022 (3)	−0.007 (2)	0.007 (2)	0.001 (2)
C07	0.029 (3)	0.035 (3)	0.029 (3)	0.004 (2)	0.004 (2)	0.000 (2)
C08	0.034 (3)	0.030 (3)	0.033 (3)	−0.009 (2)	0.008 (2)	−0.005 (2)
C09	0.104 (5)	0.036 (3)	0.037 (3)	−0.009 (3)	0.010 (3)	−0.001 (3)
C10	0.044 (3)	0.033 (3)	0.042 (3)	−0.003 (3)	0.003 (2)	0.006 (2)
C11	0.030 (3)	0.031 (3)	0.027 (3)	−0.005 (2)	0.001 (2)	−0.001 (3)
C12	0.022 (3)	0.028 (3)	0.033 (3)	0.005 (2)	−0.001 (2)	−0.006 (2)
C21	0.033 (3)	0.047 (3)	0.038 (3)	−0.004 (3)	−0.002 (2)	0.007 (3)
C22	0.040 (3)	0.055 (4)	0.046 (3)	−0.016 (3)	−0.007 (3)	0.016 (3)
C23	0.063 (4)	0.039 (3)	0.052 (4)	−0.011 (3)	−0.023 (3)	0.018 (3)
C24	0.055 (4)	0.030 (3)	0.064 (4)	0.002 (3)	−0.014 (3)	0.004 (3)
C25	0.031 (3)	0.040 (3)	0.043 (3)	0.002 (2)	−0.003 (2)	−0.003 (2)
C26	0.031 (3)	0.035 (3)	0.020 (2)	−0.004 (2)	−0.008 (2)	0.004 (2)
C27	0.028 (3)	0.034 (3)	0.026 (3)	−0.002 (2)	−0.002 (2)	−0.001 (2)
C28	0.031 (3)	0.030 (3)	0.032 (3)	−0.002 (3)	−0.006 (2)	0.004 (2)
C29	0.100 (5)	0.049 (4)	0.025 (3)	0.006 (4)	−0.010 (3)	−0.004 (3)
C30	0.047 (3)	0.035 (3)	0.040 (3)	0.009 (3)	−0.001 (2)	−0.004 (3)
N01	0.029 (2)	0.035 (3)	0.027 (2)	0.001 (2)	0.0032 (17)	−0.001 (2)
N21	0.028 (2)	0.033 (3)	0.030 (2)	−0.0008 (19)	0.0023 (17)	0.002 (2)
O02	0.0289 (18)	0.041 (2)	0.049 (2)	0.0090 (16)	−0.0089 (15)	0.0067 (17)
O03	0.0311 (19)	0.030 (2)	0.042 (2)	−0.0059 (15)	0.0012 (15)	−0.0001 (15)
O04	0.0410 (19)	0.043 (2)	0.0250 (18)	0.0117 (17)	0.0080 (14)	0.0037 (15)
O05	0.0338 (18)	0.047 (2)	0.0264 (17)	−0.0018 (17)	0.0010 (14)	−0.0060 (15)
O06	0.0232 (17)	0.041 (2)	0.0404 (19)	0.0058 (15)	−0.0010 (14)	−0.0060 (16)
O07	0.0327 (19)	0.035 (2)	0.057 (2)	−0.0085 (16)	0.0121 (16)	0.0074 (17)
O21	0.0320 (19)	0.039 (2)	0.040 (2)	−0.0056 (15)	0.0001 (14)	−0.0024 (15)
S1	0.0244 (7)	0.0293 (7)	0.0316 (7)	0.0036 (6)	−0.0001 (5)	0.0010 (6)
S2	0.0232 (6)	0.0291 (7)	0.0319 (7)	−0.0010 (6)	0.0040 (5)	−0.0019 (6)
O01	0.0238 (18)	0.042 (2)	0.048 (2)	−0.0016 (15)	−0.0022 (15)	−0.0038 (17)

Geometric parameters (Å, º)

C01—C06	1.386 (6)	C22—C23	1.375 (8)
C01—C02	1.393 (7)	C22—H22	1.02 (5)
C01—H01	0.93	C23—C24	1.355 (8)
C02—C03	1.358 (8)	C23—H23	0.93
C02—H02	0.96 (5)	C24—C25	1.378 (7)
C03—C04	1.376 (9)	C24—H24	0.91 (5)
C03—H03	1.01 (5)	C25—C26	1.391 (7)
C04—C05	1.377 (7)	C25—H25	0.93
C04—H04	0.92 (5)	C26—C27	1.529 (7)
C05—C06	1.377 (7)	C27—O21	1.431 (5)
C05—H05	0.87 (4)	C27—C28	1.519 (6)
C06—C07	1.525 (7)	C27—H27	0.95 (4)
C07—O01	1.431 (5)	C28—N21	1.500 (6)
C07—C08	1.529 (6)	C28—C29	1.519 (7)
C07—H7	1.10 (4)	C28—H28	0.87 (4)
C08—C09	1.511 (7)	C29—H29A	0.96
C08—N01	1.518 (6)	C29—H29B	0.96
C08—H08	0.98	C29—H29C	0.96
C09—H09A	0.96	C30—N21	1.487 (6)
C09—H09B	0.96	C30—H32A	0.96
C09—H09C	0.96	C30—H32B	0.96
C10—N01	1.481 (6)	C30—H32C	0.96
C10—H12A	0.96	N01—H10	0.9
C10—H12B	0.96	N01—H11	0.9
C10—H12C	0.96	N21—H30	0.9
C11—C12	1.514 (5)	N21—H31	0.9
C11—S1	1.787 (5)	O02—S1	1.458 (3)
C11—H13	0.96 (5)	O03—S1	1.454 (3)
C11—H14	0.94 (4)	O04—S1	1.456 (3)
C12—S2	1.774 (5)	O05—S2	1.457 (3)
C12—H15	0.97	O06—S2	1.457 (3)
C12—H16	0.97	O07—S2	1.454 (3)
C21—C22	1.366 (7)	O21—H26	0.82
C21—C26	1.398 (6)	O01—H06	0.82
C21—H21	0.93
C06—C01—C02	121.0 (5)	C24—C23—H23	120
C06—C01—H01	119.5	C22—C23—H23	120
C02—C01—H01	119.5	C23—C24—C25	120.7 (6)
C03—C02—C01	119.1 (6)	C23—C24—H24	121 (3)
C03—C02—H02	117 (3)	C25—C24—H24	119 (3)
C01—C02—H02	124 (3)	C24—C25—C26	120.5 (5)
C02—C03—C04	120.8 (6)	C24—C25—H25	119.7
C02—C03—H03	118 (3)	C26—C25—H25	119.7
C04—C03—H03	121 (3)	C25—C26—C21	117.4 (5)
C03—C04—C05	119.8 (6)	C25—C26—C27	123.6 (4)
C03—C04—H04	120 (3)	C21—C26—C27	119.0 (5)
C05—C04—H04	120 (3)	O21—C27—C28	107.0 (4)
C06—C05—C04	120.8 (5)	O21—C27—C26	111.7 (4)
C06—C05—H05	127 (3)	C28—C27—C26	111.5 (4)
C04—C05—H05	112 (3)	O21—C27—H27	115 (2)
C05—C06—C01	118.4 (5)	C28—C27—H27	103 (2)
C05—C06—C07	122.5 (4)	C26—C27—H27	108 (2)
C01—C06—C07	119.2 (5)	N21—C28—C27	109.2 (4)
O01—C07—C06	113.0 (4)	N21—C28—C29	108.1 (4)
O01—C07—C08	106.2 (4)	C27—C28—C29	114.2 (4)
C06—C07—C08	111.8 (4)	N21—C28—H28	103 (3)
O01—C07—H7	106 (2)	C27—C28—H28	109 (3)
C06—C07—H7	114 (2)	C29—C28—H28	113 (3)
C08—C07—H7	105 (2)	C28—C29—H29A	109.5
C09—C08—N01	108.0 (4)	C28—C29—H29B	109.5
C09—C08—C07	113.8 (4)	H29A—C29—H29B	109.5
N01—C08—C07	108.5 (4)	C28—C29—H29C	109.5
C09—C08—H08	108.9	H29A—C29—H29C	109.5
N01—C08—H08	108.9	H29B—C29—H29C	109.5
C07—C08—H08	108.9	N21—C30—H32A	109.5
C08—C09—H09A	109.5	N21—C30—H32B	109.5
C08—C09—H09B	109.5	H32A—C30—H32B	109.5
H09A—C09—H09B	109.5	N21—C30—H32C	109.5
C08—C09—H09C	109.5	H32A—C30—H32C	109.5
H09A—C09—H09C	109.5	H32B—C30—H32C	109.5
H09B—C09—H09C	109.5	C10—N01—C08	116.1 (4)
N01—C10—H12A	109.5	C10—N01—H10	108.3
N01—C10—H12B	109.5	C08—N01—H10	108.3
H12A—C10—H12B	109.5	C10—N01—H11	108.3
N01—C10—H12C	109.5	C08—N01—H11	108.3
H12A—C10—H12C	109.5	H10—N01—H11	107.4
H12B—C10—H12C	109.5	C30—N21—C28	116.9 (3)
C12—C11—S1	112.7 (3)	C30—N21—H30	108.1
C12—C11—H13	111 (3)	C28—N21—H30	108.1
S1—C11—H13	103 (3)	C30—N21—H31	108.1
C12—C11—H14	110 (2)	C28—N21—H31	108.1
S1—C11—H14	105 (2)	H30—N21—H31	107.3
H13—C11—H14	115 (4)	C27—O21—H26	109.5
C11—C12—S2	111.2 (3)	O03—S1—O04	112.99 (19)
C11—C12—H15	109.4	O03—S1—O02	113.5 (2)
S2—C12—H15	109.4	O04—S1—O02	111.9 (2)
C11—C12—H16	109.4	O03—S1—C11	105.6 (2)
S2—C12—H16	109.4	O04—S1—C11	106.5 (2)
H15—C12—H16	108	O02—S1—C11	105.6 (2)
C22—C21—C26	121.3 (5)	O07—S2—O06	114.1 (2)
C22—C21—H21	119.3	O07—S2—O05	111.2 (2)
C26—C21—H21	119.3	O06—S2—O05	112.70 (18)
C21—C22—C23	119.9 (6)	O07—S2—C12	106.3 (2)
C21—C22—H22	118 (3)	O06—S2—C12	105.5 (2)
C23—C22—H22	122 (3)	O05—S2—C12	106.4 (2)
C24—C23—C22	120.1 (6)	C07—O01—H06	109.5
C06—C01—C02—C03	1.0 (8)	C24—C25—C26—C27	−178.8 (5)
C01—C02—C03—C04	0.3 (9)	C22—C21—C26—C25	−1.7 (7)
C02—C03—C04—C05	−0.5 (9)	C22—C21—C26—C27	178.0 (4)
C03—C04—C05—C06	−0.7 (8)	C25—C26—C27—O21	23.2 (6)
C04—C05—C06—C01	1.9 (7)	C21—C26—C27—O21	−156.5 (4)
C04—C05—C06—C07	−177.7 (5)	C25—C26—C27—C28	−96.5 (6)
C02—C01—C06—C05	−2.1 (7)	C21—C26—C27—C28	83.8 (6)
C02—C01—C06—C07	177.5 (5)	O21—C27—C28—N21	59.4 (5)
C05—C06—C07—O01	21.5 (6)	C26—C27—C28—N21	−178.2 (4)
C01—C06—C07—O01	−158.1 (4)	O21—C27—C28—C29	−61.7 (5)
C05—C06—C07—C08	−98.2 (5)	C26—C27—C28—C29	60.7 (6)
C01—C06—C07—C08	82.1 (6)	C09—C08—N01—C10	179.8 (4)
O01—C07—C08—C09	−67.1 (5)	C07—C08—N01—C10	56.1 (5)
C06—C07—C08—C09	56.6 (6)	C27—C28—N21—C30	53.5 (5)
O01—C07—C08—N01	53.0 (5)	C29—C28—N21—C30	178.2 (4)
C06—C07—C08—N01	176.7 (4)	C12—C11—S1—O03	48.7 (4)
S1—C11—C12—S2	−178.4 (3)	C12—C11—S1—O04	−71.7 (4)
C26—C21—C22—C23	1.0 (8)	C12—C11—S1—O02	169.2 (3)
C21—C22—C23—C24	0.6 (9)	C11—C12—S2—O07	−68.1 (3)
C22—C23—C24—C25	−1.4 (9)	C11—C12—S2—O06	170.5 (3)
C23—C24—C25—C26	0.6 (8)	C11—C12—S2—O05	50.6 (3)
C24—C25—C26—C21	0.9 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N01—H10···O06^i	0.9	1.98	2.868 (5)	171
N01—H10···S2^i	0.9	2.88	3.642 (4)	144
N01—H11···O05^ii	0.9	2.12	2.915 (5)	147
N01—H11···S2^ii	0.9	2.88	3.614 (4)	140
N21—H30···O03^iii	0.9	1.98	2.860 (5)	164
N21—H30···S1^iii	0.9	2.95	3.717 (4)	144
N21—H31···O04^iv	0.9	2.1	2.919 (5)	151
N21—H31···S1^iv	0.9	2.9	3.648 (4)	142
O21—H26···O02^v	0.82	2	2.771 (4)	156
O21—H26···S1^v	0.82	2.96	3.778 (3)	178

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

(EPHE) (1R, 2S)-(-)-ephedrine

Crystal data

C10H16NO	F(000) = 360
Mr = 165.23	Dx = 1.114 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 15515 reflections
a = 5.6851 (4) Å	θ = 1.0–27.5°
b = 7.7047 (5) Å	µ = 0.07 mm^−1
c = 22.4819 (17) Å	T = 150 K
V = 984.75 (12) Å^3	Plate, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

KappaCCD diffractometer	1340 independent reflections
Radiation source: Enraf Nonius FR590	617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −7→7
Tmin = 0.975, Tmax = 1.061	k = −10→7
8327 measured reflections	l = −28→29

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0433P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
1340 reflections	Δρmax = 0.23 e Å^−3
154 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (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
C1	0.0038 (7)	0.0288 (5)	0.35785 (16)	0.0424 (10)
H1	−0.117 (6)	0.034 (4)	0.3892 (14)	0.051*
C2	−0.0285 (8)	−0.0706 (6)	0.3072 (2)	0.0573 (13)
H2	−0.177 (6)	−0.145 (5)	0.2999 (16)	0.069*
C3	0.1436 (10)	−0.0785 (7)	0.2651 (2)	0.0697 (16)
H3	0.126 (7)	−0.161 (6)	0.2310 (17)	0.084*
C4	0.3490 (9)	0.0151 (8)	0.27192 (17)	0.0694 (16)
H4	0.481 (8)	0.019 (6)	0.2419 (17)	0.083*
C5	0.3820 (8)	0.1170 (6)	0.32321 (15)	0.0543 (13)
H5	0.530 (6)	0.188 (5)	0.3327 (15)	0.065*
C6	0.2098 (6)	0.1225 (5)	0.36642 (15)	0.0380 (10)
C7	0.2359 (6)	0.2316 (5)	0.42236 (14)	0.0361 (10)
H7	0.169 (5)	0.152 (4)	0.4568 (13)	0.043*
C8	0.1075 (7)	0.4034 (5)	0.41872 (14)	0.0375 (10)
H8	−0.068 (6)	0.389 (5)	0.4089 (13)	0.045*
C9	0.2151 (8)	0.5247 (6)	0.37257 (18)	0.0527 (12)
H9A	0.219 (6)	0.477 (5)	0.3329 (15)	0.063*
H9B	0.395 (7)	0.555 (5)	0.3818 (15)	0.063*
H9C	0.129 (7)	0.637 (5)	0.3703 (15)	0.063*
C10	−0.0643 (8)	0.6247 (6)	0.4851 (2)	0.0532 (12)
H11A	−0.057 (6)	0.663 (5)	0.5312 (16)	0.064*
H11B	−0.228 (6)	0.579 (5)	0.4746 (15)	0.064*
H11C	−0.029 (6)	0.725 (5)	0.4629 (17)	0.064*
N1	0.0998 (6)	0.4786 (4)	0.47910 (13)	0.0414 (9)
H10	0.242 (5)	0.512 (4)	0.4858 (12)	0.015 (8)*
O1	0.4778 (4)	0.2673 (3)	0.43595 (9)	0.0449 (8)
H6	0.5239	0.1995	0.4615	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.045 (2)	0.045 (3)	0.037 (2)	0.007 (2)	−0.006 (2)	−0.005 (2)
C2	0.062 (3)	0.049 (3)	0.061 (3)	0.015 (3)	−0.026 (3)	−0.014 (2)
C3	0.082 (4)	0.074 (4)	0.053 (3)	0.035 (3)	−0.029 (3)	−0.026 (3)
C4	0.060 (3)	0.105 (4)	0.043 (3)	0.037 (3)	0.004 (3)	−0.011 (3)
C5	0.051 (2)	0.078 (4)	0.034 (2)	0.018 (3)	0.000 (2)	−0.004 (2)
C6	0.036 (2)	0.044 (3)	0.0337 (19)	0.012 (2)	−0.0032 (18)	0.0008 (19)
C7	0.0308 (19)	0.045 (3)	0.0326 (19)	0.001 (2)	−0.0019 (16)	0.0036 (19)
C8	0.039 (2)	0.040 (3)	0.033 (2)	0.001 (2)	−0.0026 (19)	0.0003 (19)
C9	0.063 (3)	0.053 (3)	0.042 (2)	0.002 (3)	0.002 (2)	0.007 (2)
C10	0.056 (3)	0.040 (3)	0.063 (3)	0.002 (3)	0.015 (2)	−0.006 (2)
N1	0.037 (2)	0.045 (2)	0.0427 (19)	−0.0042 (19)	0.0026 (16)	−0.0065 (16)
O1	0.0336 (13)	0.060 (2)	0.0414 (15)	−0.0001 (15)	−0.0061 (12)	0.0052 (12)

Geometric parameters (Å, º)

C1—C2	1.385 (5)	C7—H7	1.06 (3)
C1—C6	1.389 (5)	C8—N1	1.477 (4)
C1—H1	0.98 (3)	C8—C9	1.524 (5)
C2—C3	1.362 (6)	C8—H8	1.03 (3)
C2—H2	1.03 (4)	C9—H9A	0.97 (3)
C3—C4	1.381 (7)	C9—H9B	1.07 (4)
C3—H3	1.00 (4)	C9—H9C	1.00 (4)
C4—C5	1.408 (6)	C10—N1	1.469 (5)
C4—H4	1.01 (4)	C10—H11A	1.08 (4)
C5—C6	1.380 (5)	C10—H11B	1.02 (4)
C5—H5	1.03 (4)	C10—H11C	0.94 (4)
C6—C7	1.520 (5)	N1—H10	0.86 (3)
C7—O1	1.435 (4)	O1—H6	0.82
C7—C8	1.514 (5)
C2—C1—C6	120.9 (4)	C6—C7—H7	104.3 (17)
C2—C1—H1	121.4 (19)	N1—C8—C7	107.9 (3)
C6—C1—H1	117.7 (19)	N1—C8—C9	113.4 (4)
C3—C2—C1	120.0 (5)	C7—C8—C9	112.3 (3)
C3—C2—H2	117 (2)	N1—C8—H8	102.3 (18)
C1—C2—H2	123 (2)	C7—C8—H8	112 (2)
C2—C3—C4	120.5 (4)	C9—C8—H8	108.1 (19)
C2—C3—H3	119 (2)	C8—C9—H9A	114 (2)
C4—C3—H3	120 (2)	C8—C9—H9B	113 (2)
C3—C4—C5	119.7 (4)	H9A—C9—H9B	104 (3)
C3—C4—H4	125 (2)	C8—C9—H9C	112 (2)
C5—C4—H4	116 (2)	H9A—C9—H9C	107 (3)
C6—C5—C4	119.9 (5)	H9B—C9—H9C	107 (3)
C6—C5—H5	115 (2)	N1—C10—H11A	106.1 (19)
C4—C5—H5	125 (2)	N1—C10—H11B	107 (2)
C5—C6—C1	119.0 (4)	H11A—C10—H11B	110 (3)
C5—C6—C7	122.0 (4)	N1—C10—H11C	116 (2)
C1—C6—C7	119.0 (3)	H11A—C10—H11C	106 (3)
O1—C7—C8	107.8 (3)	H11B—C10—H11C	111 (3)
O1—C7—C6	112.1 (3)	C10—N1—C8	113.8 (3)
C8—C7—C6	113.1 (3)	C10—N1—H10	110 (2)
O1—C7—H7	107.3 (17)	C8—N1—H10	104.5 (19)
C8—C7—H7	112.1 (17)	C7—O1—H6	109.5
C6—C1—C2—C3	0.6 (6)	C1—C6—C7—O1	158.6 (3)
C1—C2—C3—C4	−1.5 (7)	C5—C6—C7—C8	99.1 (4)
C2—C3—C4—C5	1.1 (8)	C1—C6—C7—C8	−79.3 (4)
C3—C4—C5—C6	0.2 (7)	O1—C7—C8—N1	−68.2 (3)
C4—C5—C6—C1	−1.1 (6)	C6—C7—C8—N1	167.4 (3)
C4—C5—C6—C7	−179.5 (4)	O1—C7—C8—C9	57.5 (4)
C2—C1—C6—C5	0.7 (6)	C6—C7—C8—C9	−66.9 (4)
C2—C1—C6—C7	179.2 (3)	C7—C8—N1—C10	−166.9 (3)
C5—C6—C7—O1	−23.0 (5)	C9—C8—N1—C10	68.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H6···N1^i	0.82	1.96	2.778 (4)	173

Symmetry code: (i) x+1/2, −y+1/2, −z+1.

(EPHEESYL) (1R, 2S)-(-)-ephedrine esylate

Crystal data

C12H21NO4S	F(000) = 592
Mr = 275.36	Dx = 1.237 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1430 reflections
a = 5.4877 (7) Å	θ = 1.0–27.5°
b = 11.9057 (17) Å	µ = 0.23 mm^−1
c = 22.639 (4) Å	T = 150 K
V = 1479.1 (4) Å^3	Needle, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

KappaCCD diffractometer	1073 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	θmax = 28.2°, θmin = 3.2°
Graphite monochromator	h = 0→7
CCD rotation images, thick slices scans	k = 0→15
1831 measured reflections	l = 0→28
1831 independent reflections

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)] = 0.102	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.264	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 6.3635P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
1831 reflections	Δρmax = 0.33 e Å^−3
169 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (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
C1	0.674 (2)	0.2150 (9)	0.1265 (6)	0.065 (3)
H1C	0.7966	0.2317	0.1536	0.078*
C2	0.697 (2)	0.1248 (9)	0.0875 (7)	0.073 (4)
H2	0.8307	0.0776	0.0914	0.087*
C3	0.538 (3)	0.1034 (9)	0.0456 (7)	0.083 (4)
H3	0.5636	0.0449	0.0191	0.1*
C4	0.327 (3)	0.1704 (12)	0.0413 (7)	0.083 (4)
H4	0.2102	0.1557	0.0127	0.1*
C5	0.297 (2)	0.2580 (9)	0.0802 (6)	0.068 (3)
H5	0.1607	0.3039	0.0769	0.082*
C6	0.4635 (18)	0.2787 (8)	0.1235 (5)	0.052 (2)
C7	0.4312 (17)	0.3764 (7)	0.1673 (5)	0.053 (3)
H7	0.4878	0.352	0.2063	0.064*
C8	0.5694 (19)	0.4821 (8)	0.1499 (5)	0.053 (3)
H8	0.7446	0.4665	0.152	0.063*
C9	0.511 (3)	0.5260 (9)	0.0894 (5)	0.071 (3)
H9A	0.3405	0.5428	0.087	0.106*
H9B	0.5524	0.4703	0.0604	0.106*
H9C	0.6038	0.5931	0.0822	0.106*
C10	0.570 (2)	0.5481 (10)	0.2549 (6)	0.071 (4)
H12A	0.4657	0.4894	0.2693	0.106*
H12B	0.5459	0.6146	0.2781	0.106*
H12C	0.7368	0.5246	0.2578	0.106*
C11	−0.120 (2)	0.3574 (9)	0.3706 (6)	0.070 (4)
H13	−0.0833	0.4359	0.3633	0.084*
H14	−0.2952	0.3481	0.3672	0.084*
C12	−0.047 (4)	0.3296 (15)	0.4311 (7)	0.116 (6)
H15A	−0.0546	0.2498	0.4366	0.173*
H15B	−0.1543	0.3659	0.4585	0.173*
H15C	0.1171	0.355	0.4377	0.173*
N1	0.5102 (16)	0.5721 (6)	0.1926 (4)	0.053 (2)
H10	0.5901	0.6348	0.1817	0.064*
H11	0.3496	0.5868	0.1901	0.064*
O1	0.1779 (12)	0.4058 (5)	0.1715 (4)	0.060 (2)
H6	0.1577	0.4696	0.1587	0.091*
O2	0.2829 (12)	0.2952 (6)	0.3204 (5)	0.072 (2)
O3	−0.0346 (14)	0.1593 (6)	0.3292 (4)	0.072 (2)
O4	−0.0808 (14)	0.3093 (8)	0.2601 (4)	0.076 (3)
S1	0.0218 (5)	0.2757 (2)	0.31611 (14)	0.0563 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.045 (6)	0.048 (5)	0.103 (10)	−0.001 (6)	−0.002 (6)	−0.002 (6)
C2	0.051 (7)	0.046 (6)	0.122 (12)	0.013 (6)	0.003 (8)	−0.004 (7)
C3	0.091 (10)	0.045 (6)	0.113 (12)	0.005 (8)	0.014 (10)	−0.016 (6)
C4	0.066 (8)	0.085 (9)	0.099 (11)	−0.023 (8)	−0.017 (8)	−0.018 (8)
C5	0.068 (7)	0.063 (7)	0.074 (9)	0.001 (6)	−0.010 (7)	−0.020 (6)
C6	0.039 (5)	0.043 (5)	0.074 (7)	0.002 (5)	0.005 (5)	−0.003 (5)
C7	0.036 (5)	0.039 (5)	0.085 (9)	0.005 (4)	−0.002 (5)	0.003 (5)
C8	0.043 (5)	0.045 (5)	0.070 (7)	0.007 (5)	0.001 (5)	−0.003 (5)
C9	0.084 (9)	0.053 (5)	0.076 (8)	−0.032 (7)	−0.005 (8)	0.012 (5)
C10	0.074 (9)	0.075 (8)	0.062 (8)	−0.019 (7)	−0.003 (7)	−0.012 (6)
C11	0.055 (7)	0.050 (6)	0.105 (12)	0.012 (6)	−0.003 (7)	−0.005 (6)
C12	0.142 (15)	0.141 (13)	0.064 (10)	0.011 (14)	−0.011 (11)	−0.021 (8)
N1	0.039 (4)	0.041 (4)	0.080 (6)	0.003 (4)	0.001 (5)	−0.003 (4)
O1	0.041 (4)	0.039 (3)	0.102 (7)	0.007 (3)	0.002 (4)	0.006 (4)
O2	0.033 (4)	0.062 (4)	0.120 (7)	−0.013 (3)	−0.002 (4)	−0.006 (5)
O3	0.054 (4)	0.043 (4)	0.120 (7)	−0.005 (4)	0.005 (5)	−0.007 (4)
O4	0.057 (5)	0.105 (7)	0.067 (6)	−0.001 (5)	−0.005 (4)	0.004 (5)
S1	0.0447 (14)	0.0501 (13)	0.0742 (19)	−0.0012 (13)	0.0006 (15)	−0.0003 (13)

Geometric parameters (Å, º)

C1—C6	1.385 (14)	C9—H9B	0.96
C1—C2	1.395 (17)	C9—H9C	0.96
C1—H1C	0.93	C10—N1	1.476 (15)
C2—C3	1.315 (19)	C10—H12A	0.96
C2—H2	0.93	C10—H12B	0.96
C3—C4	1.406 (19)	C10—H12C	0.96
C3—H3	0.93	C11—C12	1.465 (19)
C4—C5	1.374 (17)	C11—S1	1.754 (12)
C4—H4	0.93	C11—H13	0.97
C5—C6	1.362 (15)	C11—H14	0.97
C5—H5	0.93	C12—H15A	0.96
C6—C7	1.540 (14)	C12—H15B	0.96
C7—O1	1.436 (11)	C12—H15C	0.96
C7—C8	1.521 (13)	N1—H10	0.9
C7—H7	0.98	N1—H11	0.9
C8—N1	1.480 (13)	O1—H6	0.82
C8—C9	1.500 (16)	O2—S1	1.455 (7)
C8—H8	0.98	O3—S1	1.450 (7)
C9—H9A	0.96	O4—S1	1.443 (9)
C6—C1—C2	117.6 (11)	H9A—C9—H9C	109.5
C6—C1—H1C	121.2	H9B—C9—H9C	109.5
C2—C1—H1C	121.2	N1—C10—H12A	109.5
C3—C2—C1	123.2 (11)	N1—C10—H12B	109.5
C3—C2—H2	118.4	H12A—C10—H12B	109.5
C1—C2—H2	118.4	N1—C10—H12C	109.5
C2—C3—C4	118.9 (11)	H12A—C10—H12C	109.5
C2—C3—H3	120.5	H12B—C10—H12C	109.5
C4—C3—H3	120.5	C12—C11—S1	114.2 (10)
C5—C4—C3	119.1 (13)	C12—C11—H13	108.7
C5—C4—H4	120.5	S1—C11—H13	108.7
C3—C4—H4	120.5	C12—C11—H14	108.7
C6—C5—C4	121.1 (12)	S1—C11—H14	108.7
C6—C5—H5	119.4	H13—C11—H14	107.6
C4—C5—H5	119.4	C11—C12—H15A	109.5
C5—C6—C1	119.8 (10)	C11—C12—H15B	109.5
C5—C6—C7	121.5 (9)	H15A—C12—H15B	109.5
C1—C6—C7	118.5 (10)	C11—C12—H15C	109.5
O1—C7—C8	107.4 (7)	H15A—C12—H15C	109.5
O1—C7—C6	109.7 (9)	H15B—C12—H15C	109.5
C8—C7—C6	113.6 (9)	C10—N1—C8	115.8 (8)
O1—C7—H7	108.7	C10—N1—H10	108.3
C8—C7—H7	108.7	C8—N1—H10	108.3
C6—C7—H7	108.7	C10—N1—H11	108.3
N1—C8—C9	107.3 (8)	C8—N1—H11	108.3
N1—C8—C7	108.7 (8)	H10—N1—H11	107.4
C9—C8—C7	114.8 (9)	C7—O1—H6	109.5
N1—C8—H8	108.7	O4—S1—O3	111.2 (5)
C9—C8—H8	108.7	O4—S1—O2	113.5 (6)
C7—C8—H8	108.7	O3—S1—O2	110.5 (5)
C8—C9—H9A	109.5	O4—S1—C11	106.9 (6)
C8—C9—H9B	109.5	O3—S1—C11	106.9 (6)
H9A—C9—H9B	109.5	O2—S1—C11	107.6 (6)
C8—C9—H9C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O2^i	0.9	2.03	2.904 (11)	162
N1—H10···O3^i	0.9	2.47	3.099 (11)	127
N1—H10···S1^i	0.9	2.71	3.537 (9)	153
N1—H11···O3^ii	0.9	1.98	2.852 (11)	162
O1—H6···O3^ii	0.82	2.37	3.119 (9)	152

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

(EPHEGLYC) (1R, 2S)-(-)-ephedrine glycolate

Crystal data

C12H19NO4	F(000) = 260
Mr = 241.28	Dx = 1.302 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2930 reflections
a = 9.5946 (4) Å	θ = 1.0–27.5°
b = 6.0474 (3) Å	µ = 0.10 mm^−1
c = 10.8255 (5) Å	T = 150 K
β = 101.607 (2)°	Needle, colourless
V = 615.28 (5) Å^3	0.3 × 0.05 × 0.05 mm
Z = 2

Data collection

KappaCCD diffractometer	1513 independent reflections
Radiation source: Enraf Nonius FR590	1200 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
CCD rotation images, thick slices scans	θmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −12→11
Tmin = 0.938, Tmax = 1.054	k = −7→6
4479 measured reflections	l = −14→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 0.0943P] where P = (Fo^2 + 2Fc^2)/3
1513 reflections	(Δ/σ)max = 0.008
211 parameters	Δρmax = 0.23 e Å^−3
1 restraint	Δρmin = −0.25 e Å^−3

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
C1	−0.0109 (3)	0.4855 (6)	0.8559 (3)	0.0238 (7)
H1	−0.058 (3)	0.345 (6)	0.861 (3)	0.029*
C2	0.1238 (3)	0.5263 (6)	0.9273 (3)	0.0299 (8)
H2	0.174 (3)	0.420 (7)	0.981 (3)	0.036*
C3	0.1865 (3)	0.7304 (6)	0.9218 (3)	0.0305 (8)
H3	0.282 (3)	0.757 (6)	0.971 (3)	0.037*
C4	0.1143 (3)	0.8961 (6)	0.8468 (3)	0.0291 (8)
H4	0.163 (3)	1.057 (7)	0.851 (3)	0.035*
C5	−0.0213 (3)	0.8552 (5)	0.7754 (3)	0.0231 (7)
H5	−0.070 (3)	0.973 (6)	0.723 (3)	0.028*
C6	−0.0839 (3)	0.6491 (5)	0.7784 (2)	0.0187 (6)
C7	−0.2266 (3)	0.5947 (5)	0.6942 (3)	0.0194 (6)
H7	−0.282 (3)	0.500 (6)	0.747 (3)	0.023*
C8	−0.2027 (3)	0.4557 (5)	0.5816 (2)	0.0188 (6)
H8	−0.152 (3)	0.323 (6)	0.615 (3)	0.023*
C9	−0.1232 (3)	0.5801 (6)	0.4957 (3)	0.0238 (7)
H9A	−0.037 (4)	0.621 (6)	0.538 (3)	0.029*
H9B	−0.179 (3)	0.703 (6)	0.454 (3)	0.029*
H9C	−0.108 (3)	0.497 (6)	0.423 (3)	0.029*
C10	−0.3347 (3)	0.1944 (6)	0.4189 (3)	0.0244 (6)
H12A	−0.280 (3)	0.254 (6)	0.349 (3)	0.029*
H12B	−0.434 (3)	0.162 (6)	0.368 (3)	0.029*
H12C	−0.297 (3)	0.065 (6)	0.462 (3)	0.029*
C12	−0.4983 (3)	0.1423 (5)	0.7712 (2)	0.0181 (6)
C13	−0.5625 (3)	0.2993 (5)	0.8524 (3)	0.0213 (7)
H13	−0.507 (3)	0.440 (7)	0.857 (3)	0.026*
H14	−0.659 (3)	0.335 (5)	0.809 (3)	0.026*
O1	−0.3052 (2)	0.7832 (4)	0.64316 (19)	0.0242 (5)
H6	−0.339 (3)	0.835 (6)	0.693 (3)	0.029*
O2	−0.5598 (2)	0.2123 (4)	0.97389 (17)	0.0252 (5)
H15	−0.559 (3)	0.323 (6)	1.025 (3)	0.03*
O3	−0.51542 (19)	0.1985 (4)	0.65561 (16)	0.0207 (5)
O4	−0.4317 (2)	−0.0259 (4)	0.81707 (17)	0.0278 (5)
N1	−0.3437 (2)	0.3799 (4)	0.5077 (2)	0.0187 (5)
H10	−0.393 (3)	0.483 (6)	0.462 (3)	0.022*
H11	−0.397 (3)	0.333 (5)	0.565 (3)	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0266 (15)	0.0239 (17)	0.0217 (14)	0.0045 (15)	0.0067 (12)	0.0011 (14)
C2	0.0262 (16)	0.042 (2)	0.0205 (15)	0.0119 (17)	0.0022 (12)	0.0006 (15)
C3	0.0208 (14)	0.045 (2)	0.0246 (15)	−0.0012 (16)	0.0026 (12)	−0.0083 (16)
C4	0.0261 (15)	0.033 (2)	0.0287 (16)	−0.0063 (15)	0.0078 (13)	−0.0068 (15)
C5	0.0261 (14)	0.0216 (17)	0.0223 (15)	0.0009 (14)	0.0064 (12)	−0.0015 (14)
C6	0.0205 (12)	0.0225 (17)	0.0140 (12)	0.0033 (12)	0.0057 (11)	0.0003 (12)
C7	0.0205 (13)	0.0212 (16)	0.0175 (13)	0.0010 (13)	0.0060 (11)	0.0016 (13)
C8	0.0171 (12)	0.0181 (16)	0.0212 (14)	0.0022 (13)	0.0041 (11)	0.0008 (13)
C9	0.0247 (15)	0.0254 (18)	0.0243 (16)	−0.0046 (15)	0.0121 (12)	−0.0057 (14)
C10	0.0296 (15)	0.0198 (17)	0.0239 (14)	0.0015 (15)	0.0053 (13)	−0.0033 (14)
C12	0.0184 (12)	0.0185 (17)	0.0171 (14)	−0.0021 (12)	0.0031 (11)	0.0013 (12)
C13	0.0249 (14)	0.0216 (17)	0.0174 (13)	0.0033 (14)	0.0044 (11)	0.0007 (13)
O1	0.0268 (10)	0.0258 (13)	0.0202 (10)	0.0101 (10)	0.0056 (8)	−0.0012 (10)
O2	0.0378 (11)	0.0251 (12)	0.0144 (9)	0.0042 (11)	0.0093 (8)	−0.0008 (9)
O3	0.0267 (9)	0.0203 (11)	0.0151 (9)	−0.0023 (10)	0.0043 (8)	−0.0001 (9)
O4	0.0397 (11)	0.0254 (12)	0.0208 (10)	0.0150 (11)	0.0119 (9)	0.0030 (10)
N1	0.0197 (11)	0.0187 (14)	0.0176 (12)	0.0002 (12)	0.0032 (9)	0.0005 (11)

Geometric parameters (Å, º)

C1—C2	1.388 (4)	C9—H9A	0.89 (3)
C1—C6	1.392 (4)	C9—H9B	0.97 (4)
C1—H1	0.97 (4)	C9—H9C	0.97 (4)
C2—C3	1.380 (5)	C10—N1	1.491 (4)
C2—H2	0.93 (4)	C10—H12A	1.06 (4)
C3—C4	1.384 (5)	C10—H12B	1.02 (3)
C3—H3	0.98 (3)	C10—H12C	0.94 (4)
C4—C5	1.396 (4)	C12—O4	1.249 (3)
C4—H4	1.08 (4)	C12—O3	1.275 (3)
C5—C6	1.387 (4)	C12—C13	1.508 (4)
C5—H5	0.97 (4)	C13—O2	1.411 (3)
C6—C7	1.520 (4)	C13—H13	1.00 (4)
C7—O1	1.416 (4)	C13—H14	0.97 (3)
C7—C8	1.536 (4)	O1—H6	0.75 (4)
C7—H7	1.03 (3)	O2—H15	0.87 (4)
C8—N1	1.499 (3)	N1—H10	0.88 (3)
C8—C9	1.516 (4)	N1—H11	0.92 (3)
C8—H8	0.97 (3)
C2—C1—C6	120.6 (3)	C8—C9—H9A	111 (2)
C2—C1—H1	121.0 (19)	C8—C9—H9B	111.6 (19)
C6—C1—H1	118.4 (19)	H9A—C9—H9B	113 (3)
C3—C2—C1	120.0 (3)	C8—C9—H9C	115 (2)
C3—C2—H2	118 (2)	H9A—C9—H9C	106 (3)
C1—C2—H2	122 (2)	H9B—C9—H9C	100 (3)
C2—C3—C4	120.1 (3)	N1—C10—H12A	107.8 (19)
C2—C3—H3	120 (2)	N1—C10—H12B	109 (2)
C4—C3—H3	120 (2)	H12A—C10—H12B	103 (2)
C3—C4—C5	119.9 (3)	N1—C10—H12C	112 (2)
C3—C4—H4	118.1 (18)	H12A—C10—H12C	116 (3)
C5—C4—H4	121.9 (18)	H12B—C10—H12C	109 (3)
C6—C5—C4	120.4 (3)	O4—C12—O3	124.2 (3)
C6—C5—H5	120.8 (19)	O4—C12—C13	121.1 (2)
C4—C5—H5	118.8 (19)	O3—C12—C13	114.7 (2)
C5—C6—C1	119.0 (3)	O2—C13—C12	112.1 (3)
C5—C6—C7	121.5 (3)	O2—C13—H13	111.1 (17)
C1—C6—C7	119.4 (3)	C12—C13—H13	106.8 (18)
O1—C7—C6	113.9 (3)	O2—C13—H14	111.5 (18)
O1—C7—C8	106.5 (2)	C12—C13—H14	108.9 (19)
C6—C7—C8	109.5 (2)	H13—C13—H14	106 (2)
O1—C7—H7	111.6 (17)	C7—O1—H6	109 (3)
C6—C7—H7	107.1 (15)	C13—O2—H15	108 (2)
C8—C7—H7	108.2 (17)	C10—N1—C8	114.3 (2)
N1—C8—C9	109.6 (2)	C10—N1—H10	106 (2)
N1—C8—C7	109.1 (2)	C8—N1—H10	114 (2)
C9—C8—C7	112.9 (3)	C10—N1—H11	108 (2)
N1—C8—H8	106.0 (18)	C8—N1—H11	107.5 (17)
C9—C8—H8	111.4 (18)	H10—N1—H11	106 (3)
C7—C8—H8	107.4 (18)
C6—C1—C2—C3	−0.1 (4)	C5—C6—C7—C8	101.8 (3)
C1—C2—C3—C4	1.1 (5)	C1—C6—C7—C8	−75.0 (3)
C2—C3—C4—C5	−0.9 (5)	O1—C7—C8—N1	−63.2 (3)
C3—C4—C5—C6	−0.5 (5)	C6—C7—C8—N1	173.2 (2)
C4—C5—C6—C1	1.5 (4)	O1—C7—C8—C9	59.0 (3)
C4—C5—C6—C7	−175.3 (3)	C6—C7—C8—C9	−64.5 (3)
C2—C1—C6—C5	−1.2 (4)	O4—C12—C13—O2	−10.5 (4)
C2—C1—C6—C7	175.6 (3)	O3—C12—C13—O2	170.8 (2)
C5—C6—C7—O1	−17.3 (4)	C9—C8—N1—C10	72.2 (3)
C1—C6—C7—O1	166.0 (2)	C7—C8—N1—C10	−163.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H15···O4^i	0.87 (4)	1.95 (4)	2.776 (3)	158 (3)
O2—H15···O2^i	0.87 (4)	2.62 (4)	3.2430 (15)	130 (3)
O1—H6···O4^ii	0.75 (4)	1.94 (4)	2.696 (3)	177 (3)
N1—H10···O3^iii	0.88 (3)	1.91 (4)	2.776 (3)	171 (3)

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

(EPHEHCL) (1R, 2S)-(-)-ephedrine hydrochloride

Crystal data

C10H14ClNO	F(000) = 216
Mr = 201.69	Dx = 1.229 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 11628 reflections
a = 7.2557 (3) Å	θ = 1.0–27.5°
b = 6.1228 (3) Å	µ = 0.31 mm^−1
c = 12.5486 (6) Å	T = 150 K
β = 102.223 (2)°	Needle, colourless
V = 544.84 (4) Å^3	0.3 × 0.05 × 0.05 mm
Z = 2

Data collection

KappaCCD diffractometer	2458 independent reflections
Radiation source: Enraf Nonius FR590	2006 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 3°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −9→9
Tmin = 0.926, Tmax = 1.083	k = −7→7
9528 measured reflections	l = −16→16

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)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.156	w = 1/[σ^2(Fo^2) + (0.0431P)^2 + 0.7722P] where P = (Fo^2 + 2Fc^2)/3
S = 1.19	(Δ/σ)max < 0.001
2458 reflections	Δρmax = 0.73 e Å^−3
148 parameters	Δρmin = −0.37 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (13)

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
C1	0.8557 (6)	−0.0094 (9)	0.0753 (4)	0.0290 (10)
H1	0.906 (7)	−0.151 (10)	0.103 (4)	0.035*
C2	0.8046 (7)	0.0174 (9)	−0.0373 (4)	0.0338 (12)
H2	0.839 (7)	−0.108 (10)	−0.083 (4)	0.041*
C3	0.7084 (6)	0.2047 (9)	−0.0799 (4)	0.0335 (13)
H3	0.685 (7)	0.224 (9)	−0.154 (4)	0.04*
C4	0.6663 (7)	0.3648 (9)	−0.0110 (4)	0.0361 (12)
H4	0.596 (7)	0.505 (10)	−0.039 (4)	0.043*
C5	0.7153 (6)	0.3370 (8)	0.1014 (4)	0.0297 (10)
H5	0.685 (7)	0.449 (9)	0.147 (4)	0.036*
C6	0.8108 (5)	0.1492 (11)	0.1455 (3)	0.0247 (8)
C7	0.8635 (6)	0.1080 (7)	0.2672 (3)	0.0232 (10)
H7	0.9866	0.0354	0.2839	0.028*
C8	0.7203 (6)	−0.0402 (8)	0.3033 (3)	0.0214 (9)
H8	0.690 (6)	−0.169 (9)	0.259 (4)	0.026*
C9	0.5321 (6)	0.0728 (7)	0.3037 (4)	0.0259 (10)
H10A	0.4413	−0.034	0.3151	0.039*
H10B	0.4876	0.1441	0.2349	0.039*
H10C	0.5494	0.179	0.3612	0.039*
C10	0.6985 (6)	−0.3065 (8)	0.4550 (4)	0.0319 (12)
H12A	0.5758	−0.2548	0.4602	0.048*
H12B	0.7653	−0.355	0.5253	0.048*
H12C	0.6855	−0.4258	0.4043	0.048*
N1	0.8064 (5)	−0.1248 (7)	0.4160 (3)	0.0248 (8)
H10	0.927 (7)	−0.196 (8)	0.411 (4)	0.03*
H11	0.804 (7)	−0.019 (9)	0.460 (4)	0.03*
O1	0.8740 (5)	0.2991 (6)	0.3322 (3)	0.0315 (8)
H6	0.956 (8)	0.404 (10)	0.325 (4)	0.038*
Cl1	1.17971 (13)	−0.34367 (18)	0.37349 (7)	0.0267 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.028 (2)	0.030 (3)	0.031 (2)	0.002 (2)	0.0095 (19)	0.002 (2)
C2	0.035 (3)	0.039 (3)	0.033 (3)	−0.010 (2)	0.019 (2)	−0.011 (2)
C3	0.029 (2)	0.049 (4)	0.024 (2)	−0.009 (2)	0.0076 (17)	0.005 (2)
C4	0.029 (2)	0.038 (3)	0.041 (3)	0.006 (2)	0.009 (2)	0.012 (2)
C5	0.029 (2)	0.031 (3)	0.031 (2)	0.002 (2)	0.0106 (19)	0.002 (2)
C6	0.0205 (16)	0.028 (2)	0.027 (2)	−0.001 (2)	0.0080 (14)	0.002 (3)
C7	0.0222 (19)	0.021 (3)	0.026 (2)	0.0009 (16)	0.0039 (15)	−0.0019 (17)
C8	0.018 (2)	0.025 (2)	0.020 (2)	0.0008 (17)	0.0034 (15)	−0.0046 (18)
C9	0.020 (2)	0.028 (2)	0.029 (2)	−0.0002 (17)	0.0040 (17)	−0.0039 (18)
C10	0.034 (2)	0.032 (3)	0.032 (2)	−0.011 (2)	0.0095 (17)	0.001 (2)
N1	0.0247 (18)	0.025 (2)	0.0259 (19)	−0.0050 (16)	0.0072 (15)	−0.0020 (16)
O1	0.0358 (17)	0.0290 (19)	0.0312 (17)	−0.0162 (15)	0.0108 (14)	−0.0091 (15)
Cl1	0.0221 (4)	0.0298 (5)	0.0289 (5)	−0.0045 (5)	0.0068 (3)	0.0017 (6)

Geometric parameters (Å, º)

C1—C2	1.392 (7)	C7—H7	0.98
C1—C6	1.395 (7)	C8—N1	1.512 (5)
C1—H1	0.97 (6)	C8—C9	1.532 (6)
C2—C3	1.389 (8)	C8—H8	0.96 (5)
C2—H2	1.02 (6)	C9—H10A	0.96
C3—C4	1.383 (7)	C9—H10B	0.96
C3—H3	0.92 (5)	C9—H10C	0.96
C4—C5	1.391 (7)	C10—N1	1.500 (6)
C4—H4	1.02 (6)	C10—H12A	0.96
C5—C6	1.395 (8)	C10—H12B	0.96
C5—H5	0.95 (6)	C10—H12C	0.96
C6—C7	1.515 (5)	N1—H10	0.99 (5)
C7—O1	1.419 (5)	N1—H11	0.85 (5)
C7—C8	1.519 (6)	O1—H6	0.89 (6)
C2—C1—C6	120.7 (5)	N1—C8—C9	110.1 (3)
C2—C1—H1	118 (3)	C7—C8—C9	113.4 (4)
C6—C1—H1	121 (3)	N1—C8—H8	105 (3)
C3—C2—C1	119.5 (5)	C7—C8—H8	114 (3)
C3—C2—H2	125 (3)	C9—C8—H8	106 (3)
C1—C2—H2	116 (3)	C8—C9—H10A	109.5
C4—C3—C2	120.2 (4)	C8—C9—H10B	109.5
C4—C3—H3	121 (3)	H10A—C9—H10B	109.5
C2—C3—H3	118 (3)	C8—C9—H10C	109.5
C3—C4—C5	120.3 (5)	H10A—C9—H10C	109.5
C3—C4—H4	123 (3)	H10B—C9—H10C	109.5
C5—C4—H4	117 (3)	N1—C10—H12A	109.5
C4—C5—C6	120.1 (5)	N1—C10—H12B	109.5
C4—C5—H5	119 (3)	H12A—C10—H12B	109.5
C6—C5—H5	121 (3)	N1—C10—H12C	109.5
C1—C6—C5	119.1 (4)	H12A—C10—H12C	109.5
C1—C6—C7	118.6 (5)	H12B—C10—H12C	109.5
C5—C6—C7	122.3 (4)	C10—N1—C8	114.7 (3)
O1—C7—C6	114.4 (4)	C10—N1—H10	103 (3)
O1—C7—C8	106.1 (3)	C8—N1—H10	107 (3)
C6—C7—C8	111.0 (4)	C10—N1—H11	106 (3)
O1—C7—H7	108.4	C8—N1—H11	106 (3)
C6—C7—H7	108.4	H10—N1—H11	121 (4)
C8—C7—H7	108.4	C7—O1—H6	119 (3)
N1—C8—C7	108.1 (3)
C6—C1—C2—C3	0.2 (7)	C5—C6—C7—O1	−22.3 (6)
C1—C2—C3—C4	1.0 (7)	C1—C6—C7—C8	−80.7 (5)
C2—C3—C4—C5	−1.8 (7)	C5—C6—C7—C8	97.7 (5)
C3—C4—C5—C6	1.3 (7)	O1—C7—C8—N1	−70.6 (4)
C2—C1—C6—C5	−0.7 (7)	C6—C7—C8—N1	164.5 (4)
C2—C1—C6—C7	177.8 (4)	O1—C7—C8—C9	51.8 (4)
C4—C5—C6—C1	−0.1 (7)	C6—C7—C8—C9	−73.1 (5)
C4—C5—C6—C7	−178.5 (4)	C7—C8—N1—C10	−168.8 (4)
C1—C6—C7—O1	159.2 (4)	C9—C8—N1—C10	66.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···Cl1^i	0.85 (5)	2.33 (5)	3.136 (4)	157 (5)
O1—H6···Cl1^ii	0.89 (6)	2.23 (6)	3.080 (3)	159 (4)

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

(EPHEHEMI) (1R, 2S)-(-)-ephedrine hemihydrate

Crystal data

C10H15NO	F(000) = 760
Mr = 174.24	Dx = 1.157 Mg m^−3
Orthorhombic, C2221	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 8739 reflections
a = 7.3639 (4) Å	θ = 1.0–25.0°
b = 11.2551 (6) Å	µ = 0.08 mm^−1
c = 24.1442 (16) Å	T = 150 K
V = 2001.1 (2) Å^3	Plate, colourless
Z = 8	0.25 × 0.25 × 0.05 mm

Data collection

KappaCCD diffractometer	1007 independent reflections
Radiation source: Enraf Nonius FR590	801 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
CCD rotation images, thick slices scans	θmax = 25°, θmin = 3.7°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −8→8
Tmin = 0.976, Tmax = 1.02	k = −13→13
5306 measured reflections	l = −28→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 0.566P] where P = (Fo^2 + 2Fc^2)/3
1007 reflections	(Δ/σ)max = 0.001
151 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

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
C1	0.3249 (6)	0.3337 (4)	0.60488 (13)	0.0592 (11)
H1	0.302 (6)	0.395 (4)	0.6318 (17)	0.071*
C2	0.4242 (7)	0.3626 (6)	0.55793 (17)	0.0883 (18)
H2	0.458 (8)	0.438 (5)	0.553 (2)	0.106*
C3	0.4752 (6)	0.2761 (7)	0.52123 (17)	0.0889 (18)
H3	0.541	0.2955	0.4896	0.107*
C4	0.4286 (7)	0.1618 (7)	0.53154 (16)	0.0859 (19)
H4	0.470 (7)	0.103 (4)	0.510 (2)	0.103*
C5	0.3290 (6)	0.1322 (4)	0.57806 (13)	0.0564 (10)
H5	0.296 (6)	0.054 (3)	0.5870 (16)	0.068*
C6	0.2740 (4)	0.2179 (3)	0.61511 (12)	0.0368 (7)
C7	0.1604 (4)	0.1856 (3)	0.66467 (11)	0.0287 (7)
H7	0.188 (4)	0.100 (3)	0.6764 (11)	0.034*
C8	−0.0439 (4)	0.1851 (2)	0.65060 (11)	0.0294 (7)
H8	−0.057 (4)	0.134 (3)	0.6167 (13)	0.035*
C9	−0.1189 (5)	0.3083 (3)	0.63911 (16)	0.0429 (8)
H9A	−0.252 (5)	0.303 (3)	0.6291 (13)	0.051*
H9B	−0.109 (5)	0.355 (3)	0.6726 (15)	0.051*
H9C	−0.051 (5)	0.346 (3)	0.6083 (15)	0.051*
C10	−0.3349 (4)	0.1031 (3)	0.68479 (12)	0.0453 (9)
H11A	−0.4058	0.1741	0.689	0.068*
H11B	−0.3784	0.0435	0.7099	0.068*
H11C	−0.3456	0.0747	0.6474	0.068*
N1	−0.1429 (3)	0.1293 (2)	0.69701 (9)	0.0308 (6)
H10	−0.088 (4)	0.064 (3)	0.7083 (13)	0.029 (8)*
O1	0.1982 (3)	0.26304 (17)	0.70953 (7)	0.0341 (5)
H6	0.1708	0.2304	0.7387	0.051*
O2	0.5	0.3973 (3)	0.75	0.0435 (8)
H13	0.417 (4)	0.349 (3)	0.7382 (14)	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.070 (3)	0.076 (3)	0.0313 (17)	−0.039 (2)	0.0065 (18)	−0.0029 (16)
C2	0.088 (3)	0.144 (4)	0.033 (2)	−0.079 (3)	0.004 (2)	0.003 (3)
C3	0.037 (2)	0.196 (6)	0.033 (2)	−0.013 (3)	0.0028 (18)	0.017 (3)
C4	0.071 (3)	0.152 (5)	0.035 (2)	0.064 (4)	0.012 (2)	0.002 (3)
C5	0.060 (2)	0.077 (2)	0.0315 (17)	0.035 (2)	0.0021 (17)	0.0019 (17)
C6	0.0259 (15)	0.058 (2)	0.0264 (14)	0.0019 (14)	−0.0065 (13)	−0.0008 (14)
C7	0.0291 (15)	0.0304 (15)	0.0266 (14)	−0.0008 (14)	−0.0030 (12)	−0.0038 (12)
C8	0.0284 (15)	0.0363 (16)	0.0236 (15)	0.0026 (14)	−0.0026 (12)	0.0000 (13)
C9	0.0379 (18)	0.0461 (19)	0.0447 (19)	0.0109 (15)	0.0008 (16)	0.0122 (16)
C10	0.0358 (18)	0.063 (2)	0.0371 (17)	−0.0129 (17)	−0.0036 (16)	−0.0052 (15)
N1	0.0270 (13)	0.0344 (13)	0.0309 (12)	−0.0022 (12)	−0.0049 (11)	0.0028 (11)
O1	0.0349 (11)	0.0428 (11)	0.0247 (10)	−0.0095 (9)	−0.0020 (9)	−0.0002 (8)
O2	0.0360 (19)	0.0310 (16)	0.063 (2)	0	−0.0119 (16)	0

Geometric parameters (Å, º)

C1—C6	1.379 (5)	C7—H7	1.03 (3)
C1—C2	1.387 (5)	C8—N1	1.477 (4)
C1—H1	0.96 (4)	C8—C9	1.518 (4)
C2—C3	1.369 (8)	C8—H8	1.01 (3)
C2—H2	0.89 (5)	C9—H9A	1.01 (4)
C3—C4	1.354 (7)	C9—H9B	0.97 (4)
C3—H3	0.93	C9—H9C	0.99 (3)
C4—C5	1.382 (6)	C10—N1	1.474 (4)
C4—H4	0.90 (5)	C10—H11A	0.96
C5—C6	1.376 (5)	C10—H11B	0.96
C5—H5	0.93 (4)	C10—H11C	0.96
C6—C7	1.505 (4)	N1—H10	0.88 (3)
C7—O1	1.418 (3)	O1—H6	0.82
C7—C8	1.543 (4)	O2—H13	0.86 (3)
C6—C1—C2	120.7 (4)	C8—C7—H7	104.6 (19)
C6—C1—H1	121 (2)	N1—C8—C9	110.3 (3)
C2—C1—H1	118 (3)	N1—C8—C7	108.4 (2)
C3—C2—C1	120.4 (5)	C9—C8—C7	113.0 (3)
C3—C2—H2	121 (4)	N1—C8—H8	108.8 (17)
C1—C2—H2	119 (4)	C9—C8—H8	110.0 (17)
C4—C3—C2	119.1 (4)	C7—C8—H8	106.1 (17)
C4—C3—H3	120.4	C8—C9—H9A	110 (2)
C2—C3—H3	120.4	C8—C9—H9B	108 (2)
C3—C4—C5	120.9 (5)	H9A—C9—H9B	108 (3)
C3—C4—H4	121 (3)	C8—C9—H9C	110 (2)
C5—C4—H4	118 (3)	H9A—C9—H9C	110 (3)
C6—C5—C4	121.0 (4)	H9B—C9—H9C	111 (3)
C6—C5—H5	115 (3)	N1—C10—H11A	109.5
C4—C5—H5	124 (3)	N1—C10—H11B	109.5
C5—C6—C1	117.8 (3)	H11A—C10—H11B	109.5
C5—C6—C7	120.7 (3)	N1—C10—H11C	109.5
C1—C6—C7	121.5 (3)	H11A—C10—H11C	109.5
O1—C7—C6	110.5 (2)	H11B—C10—H11C	109.5
O1—C7—C8	111.2 (2)	C10—N1—C8	114.0 (2)
C6—C7—C8	111.6 (2)	C10—N1—H10	109.7 (18)
O1—C7—H7	109.2 (16)	C8—N1—H10	111.2 (19)
C6—C7—H7	109.6 (17)	C7—O1—H6	109.5
C6—C1—C2—C3	−0.8 (7)	C1—C6—C7—O1	−31.6 (4)
C1—C2—C3—C4	−0.4 (7)	C5—C6—C7—C8	−86.6 (3)
C2—C3—C4—C5	0.8 (7)	C1—C6—C7—C8	92.7 (4)
C3—C4—C5—C6	0.1 (6)	O1—C7—C8—N1	−67.7 (3)
C4—C5—C6—C1	−1.3 (5)	C6—C7—C8—N1	168.5 (2)
C4—C5—C6—C7	178.0 (3)	O1—C7—C8—C9	55.0 (3)
C2—C1—C6—C5	1.7 (6)	C6—C7—C8—C9	−68.9 (3)
C2—C1—C6—C7	−177.7 (4)	C9—C8—N1—C10	66.3 (3)
C5—C6—C7—O1	149.1 (3)	C7—C8—N1—C10	−169.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O2^i	0.88 (3)	2.23 (3)	3.092 (4)	167 (3)
O1—H6···N1^ii	0.82	1.93	2.743 (3)	168

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

(EPHEMALA) (1R, 2S)-(-)-ephedrine L-(-)-malate

Crystal data

C14H21NO6	F(000) = 320
Mr = 299.32	Dx = 1.31 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 17480 reflections
a = 6.1312 (6) Å	θ = 2.0–25.0°
b = 9.1719 (10) Å	µ = 0.10 mm^−1
c = 13.7393 (17) Å	T = 293 K
β = 100.909 (4)°	Plate, colourless
V = 758.66 (15) Å^3	0.25 × 0.25 × 0.1 mm
Z = 2

Data collection

KappaCCD diffractometer	1713 independent reflections
Radiation source: Enraf Nonius FR590	1232 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.109
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 2.7°
CCD rotation images, thick slices scans	h = −7→7
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	k = −10→11
Tmin = 0.912, Tmax = 1.134	l = −15→17
6933 measured reflections

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.185	w = 1/[σ^2(Fo^2) + (0.0999P)^2 + 0.0445P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
1713 reflections	Δρmax = 0.26 e Å^−3
213 parameters	Δρmin = −0.30 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 10 (10)

Special details

Experimental. Structures of 17 salts of ephedrine: Crystal packing and hydrogen bonding analysis

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
C1	0.0631 (11)	0.2120 (7)	0.3731 (5)	0.0442 (15)
H1	−0.0393	0.1552	0.3309	0.053*
C2	0.1200 (12)	0.1756 (8)	0.4714 (6)	0.0544 (18)
H2	0.0542	0.0955	0.4957	0.065*
C3	0.2732 (13)	0.2567 (9)	0.5337 (5)	0.0526 (18)
H3	0.314 (12)	0.241 (10)	0.587 (6)	0.063*
C4	0.3665 (11)	0.3788 (9)	0.4986 (5)	0.0475 (16)
H4	0.472 (12)	0.445 (9)	0.542 (6)	0.057*
C5	0.3078 (9)	0.4149 (8)	0.3997 (5)	0.0396 (14)
H5	0.384 (10)	0.512 (8)	0.388 (5)	0.047*
C6	0.1559 (9)	0.3319 (6)	0.3361 (5)	0.0337 (13)
C7	0.0991 (8)	0.3755 (6)	0.2272 (4)	0.0294 (12)
H7	0.247 (9)	0.401 (7)	0.199 (4)	0.035*
C8	−0.0623 (8)	0.5035 (6)	0.2096 (4)	0.0272 (11)
H8	0.001 (9)	0.585 (8)	0.240 (4)	0.033*
C9	−0.2807 (9)	0.4759 (7)	0.2413 (5)	0.0373 (13)
H9A	−0.3786	0.5568	0.2219	0.056*
H9B	−0.2562	0.4646	0.312	0.056*
H9C	−0.3465	0.3886	0.2101	0.056*
C10	0.0904 (9)	0.5631 (7)	0.0559 (5)	0.0384 (14)
H12A	0.2026	0.6165	0.0999	0.058*
H12B	0.0487	0.6159	−0.0051	0.058*
H12C	0.1476	0.4692	0.0426	0.058*
C11	0.2994 (8)	−0.1015 (6)	0.2301 (4)	0.0280 (12)
C12	0.4963 (8)	0.0001 (6)	0.2406 (4)	0.0297 (12)
H13	0.6237	−0.0459	0.2817	0.036*
H14	0.4634	0.0886	0.2737	0.036*
C13	0.5549 (8)	0.0401 (6)	0.1398 (4)	0.0270 (11)
H15	0.700 (10)	0.087 (7)	0.145 (4)	0.032*
C14	0.5836 (8)	−0.1006 (6)	0.0837 (4)	0.0276 (11)
N1	−0.1073 (7)	0.5439 (5)	0.1027 (3)	0.0289 (10)
H10	−0.1942	0.4744	0.0691	0.035*
H11	−0.1853	0.6276	0.0958	0.035*
O1	−0.0033 (6)	0.2631 (4)	0.1639 (3)	0.0348 (9)
H6	0.0905	0.203	0.1557	0.052*
O2	0.3888 (6)	0.1340 (4)	0.0873 (3)	0.0328 (9)
H16	0.4469	0.1946	0.0564	0.049*
O3	0.1126 (6)	−0.0354 (4)	0.1911 (3)	0.0404 (11)
H17	0.0127	−0.0958	0.1781	0.061*
O4	0.3119 (6)	−0.2288 (5)	0.2511 (4)	0.0445 (11)
O5	0.4475 (6)	−0.1366 (4)	0.0085 (3)	0.0332 (9)
O6	0.7526 (6)	−0.1770 (4)	0.1212 (3)	0.0333 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.056 (3)	0.029 (3)	0.045 (4)	−0.003 (3)	0.000 (3)	0.001 (3)
C2	0.071 (4)	0.041 (4)	0.047 (4)	−0.008 (4)	0.000 (3)	0.010 (3)
C3	0.071 (4)	0.056 (4)	0.028 (3)	0.000 (4)	0.001 (3)	0.011 (3)
C4	0.047 (3)	0.055 (4)	0.036 (4)	−0.008 (3)	−0.003 (3)	−0.004 (3)
C5	0.038 (3)	0.044 (4)	0.035 (3)	−0.003 (3)	0.003 (2)	−0.004 (3)
C6	0.033 (3)	0.030 (3)	0.037 (3)	0.003 (2)	0.004 (2)	0.001 (3)
C7	0.023 (2)	0.027 (3)	0.036 (3)	0.001 (2)	0.002 (2)	−0.002 (2)
C8	0.031 (3)	0.020 (2)	0.031 (3)	0.000 (2)	0.006 (2)	−0.001 (2)
C9	0.035 (3)	0.037 (3)	0.040 (3)	0.004 (3)	0.008 (2)	0.006 (3)
C10	0.030 (3)	0.048 (4)	0.039 (3)	0.001 (3)	0.012 (2)	0.003 (3)
C11	0.027 (2)	0.023 (3)	0.034 (3)	0.000 (2)	0.005 (2)	0.001 (2)
C12	0.030 (2)	0.025 (3)	0.032 (3)	−0.001 (2)	−0.001 (2)	−0.002 (2)
C13	0.025 (2)	0.021 (2)	0.033 (3)	0.003 (2)	0.001 (2)	0.005 (2)
C14	0.024 (2)	0.026 (3)	0.032 (3)	0.002 (2)	0.005 (2)	0.003 (2)
N1	0.030 (2)	0.026 (2)	0.028 (3)	0.0022 (19)	0.0007 (18)	0.001 (2)
O1	0.0373 (19)	0.0210 (18)	0.044 (2)	0.0033 (17)	0.0014 (17)	−0.0067 (18)
O2	0.0306 (19)	0.0215 (18)	0.046 (3)	0.0024 (15)	0.0056 (17)	0.0051 (17)
O3	0.0287 (19)	0.025 (2)	0.065 (3)	−0.0012 (16)	0.0031 (19)	0.006 (2)
O4	0.036 (2)	0.028 (2)	0.065 (3)	−0.0015 (17)	−0.0009 (19)	0.009 (2)
O5	0.0320 (18)	0.0259 (19)	0.040 (2)	0.0027 (16)	0.0014 (16)	0.0013 (17)
O6	0.0307 (18)	0.0249 (18)	0.042 (3)	0.0025 (16)	0.0022 (16)	0.0010 (17)

Geometric parameters (Å, º)

C1—C2	1.371 (9)	C10—N1	1.487 (7)
C1—C6	1.378 (9)	C10—H12A	0.96
C1—H1	0.93	C10—H12B	0.96
C2—C3	1.365 (11)	C10—H12C	0.96
C2—H2	0.93	C11—O4	1.201 (7)
C3—C4	1.385 (11)	C11—O3	1.317 (6)
C3—H3	0.74 (8)	C11—C12	1.511 (7)
C4—C5	1.379 (9)	C12—C13	1.540 (8)
C4—H4	1.00 (8)	C12—H13	0.97
C5—C6	1.379 (8)	C12—H14	0.97
C5—H5	1.03 (7)	C13—O2	1.422 (6)
C6—C7	1.525 (8)	C13—C14	1.530 (7)
C7—O1	1.416 (6)	C13—H15	0.98 (6)
C7—C8	1.525 (7)	C14—O5	1.243 (7)
C7—H7	1.08 (6)	C14—O6	1.277 (6)
C8—N1	1.488 (7)	N1—H10	0.9
C8—C9	1.506 (7)	N1—H11	0.9
C8—H8	0.91 (7)	O1—H6	0.82
C9—H9A	0.96	O2—H16	0.82
C9—H9B	0.96	O3—H17	0.82
C9—H9C	0.96
C2—C1—C6	120.8 (6)	H9B—C9—H9C	109.5
C2—C1—H1	119.6	N1—C10—H12A	109.5
C6—C1—H1	119.6	N1—C10—H12B	109.5
C3—C2—C1	120.1 (6)	H12A—C10—H12B	109.5
C3—C2—H2	119.9	N1—C10—H12C	109.5
C1—C2—H2	119.9	H12A—C10—H12C	109.5
C2—C3—C4	120.2 (7)	H12B—C10—H12C	109.5
C2—C3—H3	125 (7)	O4—C11—O3	123.8 (5)
C4—C3—H3	115 (7)	O4—C11—C12	124.3 (5)
C5—C4—C3	119.3 (7)	O3—C11—C12	111.9 (4)
C5—C4—H4	118 (4)	C11—C12—C13	112.3 (4)
C3—C4—H4	123 (4)	C11—C12—H13	109.1
C6—C5—C4	120.7 (6)	C13—C12—H13	109.1
C6—C5—H5	131 (4)	C11—C12—H14	109.1
C4—C5—H5	109 (4)	C13—C12—H14	109.1
C1—C6—C5	118.9 (6)	H13—C12—H14	107.9
C1—C6—C7	122.5 (5)	O2—C13—C14	113.2 (4)
C5—C6—C7	118.6 (5)	O2—C13—C12	109.5 (4)
O1—C7—C6	113.9 (5)	C14—C13—C12	108.7 (4)
O1—C7—C8	105.3 (4)	O2—C13—H15	109 (4)
C6—C7—C8	112.2 (5)	C14—C13—H15	103 (4)
O1—C7—H7	104 (3)	C12—C13—H15	114 (3)
C6—C7—H7	111 (3)	O5—C14—O6	123.8 (5)
C8—C7—H7	110 (3)	O5—C14—C13	121.3 (4)
N1—C8—C9	108.5 (4)	O6—C14—C13	114.9 (4)
N1—C8—C7	110.0 (4)	C10—N1—C8	116.2 (4)
C9—C8—C7	114.2 (5)	C10—N1—H10	108.2
N1—C8—H8	104 (4)	C8—N1—H10	108.2
C9—C8—H8	109 (4)	C10—N1—H11	108.2
C7—C8—H8	111 (4)	C8—N1—H11	108.2
C8—C9—H9A	109.5	H10—N1—H11	107.4
C8—C9—H9B	109.5	C7—O1—H6	109.5
H9A—C9—H9B	109.5	C13—O2—H16	109.5
C8—C9—H9C	109.5	C11—O3—H17	109.5
H9A—C9—H9C	109.5
C6—C1—C2—C3	−1.2 (11)	C6—C7—C8—N1	178.6 (4)
C1—C2—C3—C4	2.0 (12)	O1—C7—C8—C9	65.2 (6)
C2—C3—C4—C5	−1.8 (12)	C6—C7—C8—C9	−59.2 (6)
C3—C4—C5—C6	0.8 (10)	O4—C11—C12—C13	106.6 (6)
C2—C1—C6—C5	0.2 (9)	O3—C11—C12—C13	−70.7 (6)
C2—C1—C6—C7	179.4 (6)	C11—C12—C13—O2	71.0 (5)
C4—C5—C6—C1	0.0 (9)	C11—C12—C13—C14	−53.2 (5)
C4—C5—C6—C7	−179.2 (6)	O2—C13—C14—O5	−11.5 (7)
C1—C6—C7—O1	−17.0 (7)	C12—C13—C14—O5	110.5 (6)
C5—C6—C7—O1	162.2 (5)	O2—C13—C14—O6	169.9 (4)
C1—C6—C7—C8	102.5 (6)	C12—C13—C14—O6	−68.2 (6)
C5—C6—C7—C8	−78.3 (6)	C9—C8—N1—C10	−175.0 (5)
O1—C7—C8—N1	−57.1 (5)	C7—C8—N1—C10	−49.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O5^i	0.9	1.99	2.867 (6)	165
N1—H11···O6^ii	0.9	1.88	2.727 (6)	156
O2—H16···O5^iii	0.82	1.96	2.769 (5)	170

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

(EPHEMALE) (1R, 2S)-(-)-ephedrine maleate monohydrate

Crystal data

C12H12NO4	F(000) = 640
Mr = 299.32	Dx = 1.273 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12306 reflections
a = 5.6370 (2) Å	θ = 4.1–27.5°
b = 13.4950 (5) Å	µ = 0.1 mm^−1
c = 20.5250 (5) Å	T = 150 K
V = 1561.36 (9) Å^3	Needle, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

KappaCCD diffractometer	1712 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	θmax = 27.5°, θmin = 4.1°
Graphite monochromator	h = −6→7
CCD rotation images, thick slices scans	k = −17→17
11592 measured reflections	l = −21→25
1996 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 0.2281P] where P = (Fo^2 + 2Fc^2)/3
1996 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

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
C1	0.7193 (4)	0.02778 (16)	0.10470 (10)	0.0293 (5)
H1	0.8515	−0.0061	0.0838	0.035*
C2	0.7626 (4)	0.07003 (18)	0.16530 (10)	0.0352 (5)
H2	0.9351	0.0554	0.1826	0.042*
C3	0.5922 (5)	0.12873 (17)	0.19428 (11)	0.0379 (5)
H3	0.6147	0.1584	0.2381	0.045*
C4	0.3802 (5)	0.14626 (17)	0.16295 (11)	0.0380 (5)
H4	0.2472	0.186	0.1793	0.046*
C5	0.3363 (4)	0.10395 (17)	0.10224 (10)	0.0318 (5)
H5	0.1832	0.1099	0.0857	0.038*
C6	0.5055 (4)	0.04414 (15)	0.07267 (9)	0.0251 (4)
C7	0.4589 (4)	−0.00311 (15)	0.00663 (9)	0.0240 (4)
H7	0.5238	−0.0742	0.0102	0.029*
C8	0.5904 (4)	0.05299 (15)	−0.04737 (9)	0.0270 (4)
H8	0.7683	0.0485	−0.0395	0.032*
C9	0.5209 (6)	0.16161 (17)	−0.05193 (11)	0.0442 (6)
H9A	0.6032	0.1919	−0.0877	0.066*
H9B	0.5627	0.1947	−0.0122	0.066*
H9C	0.3529	0.1668	−0.0588	0.066*
C10	0.5986 (5)	−0.09858 (16)	−0.12049 (11)	0.0361 (5)
H12A	0.7634	−0.107	−0.11	0.054*
H12B	0.5716	−0.1181	−0.1649	0.054*
H12C	0.5041	−0.139	−0.092	0.054*
C11	0.4881 (4)	0.41800 (16)	0.20953 (10)	0.0282 (4)
C12	0.6532 (4)	0.39022 (17)	0.26328 (10)	0.0287 (5)
H13	0.8124	0.4033	0.2544	0.034*
C13	0.6134 (4)	0.34417 (16)	0.31996 (10)	0.0280 (4)
H14	0.7528	0.3338	0.3445	0.034*
C14	0.3868 (4)	0.30580 (15)	0.34815 (9)	0.0254 (4)
O1	0.2161 (3)	−0.00389 (13)	−0.01055 (7)	0.0314 (3)
O2	0.5673 (3)	0.46479 (14)	0.16280 (8)	0.0422 (4)
O3	0.2668 (3)	0.39346 (12)	0.21329 (7)	0.0296 (3)
O4	0.1941 (3)	0.30615 (12)	0.31439 (7)	0.0320 (4)
H15	0.2228	0.3339	0.2716	0.038*
O5	0.3894 (3)	0.27414 (13)	0.40451 (7)	0.0358 (4)
O6	−0.0138 (3)	0.31905 (12)	0.47903 (8)	0.0377 (4)
H16	0.1163	0.2981	0.4541	0.045*
N1	0.5318 (3)	0.00672 (13)	−0.11208 (8)	0.0262 (4)
H6	0.152 (6)	−0.061 (3)	0.0027 (13)	0.064 (10)*
H10	0.607 (5)	0.0451 (19)	−0.1476 (11)	0.031 (6)*
H11	0.372 (5)	0.019 (2)	−0.1212 (11)	0.035 (6)*
H17	0.012 (6)	0.287 (2)	0.5127 (14)	0.049 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0281 (10)	0.0323 (11)	0.0273 (10)	−0.0002 (9)	0.0005 (8)	0.0000 (8)
C2	0.0351 (12)	0.0408 (12)	0.0298 (11)	−0.0035 (11)	−0.0045 (9)	0.0014 (9)
C3	0.0521 (15)	0.0331 (12)	0.0285 (11)	−0.0029 (11)	−0.0022 (11)	−0.0047 (9)
C4	0.0480 (14)	0.0302 (12)	0.0358 (12)	0.0057 (11)	0.0059 (11)	−0.0038 (9)
C5	0.0343 (12)	0.0297 (11)	0.0312 (11)	0.0031 (9)	0.0002 (9)	0.0001 (8)
C6	0.0290 (10)	0.0240 (9)	0.0223 (10)	−0.0016 (9)	0.0023 (8)	0.0034 (7)
C7	0.0257 (10)	0.0254 (9)	0.0209 (9)	−0.0014 (9)	0.0009 (7)	0.0028 (7)
C8	0.0300 (11)	0.0299 (11)	0.0211 (10)	−0.0067 (9)	0.0002 (8)	0.0009 (7)
C9	0.0728 (19)	0.0275 (11)	0.0322 (12)	−0.0091 (12)	0.0089 (12)	0.0034 (8)
C10	0.0485 (13)	0.0301 (11)	0.0296 (11)	−0.0019 (11)	0.0042 (10)	−0.0013 (8)
C11	0.0256 (10)	0.0344 (11)	0.0246 (10)	0.0041 (9)	0.0035 (8)	0.0018 (8)
C12	0.0203 (10)	0.0377 (12)	0.0281 (11)	−0.0006 (9)	0.0014 (8)	0.0035 (8)
C13	0.0229 (10)	0.0345 (11)	0.0268 (10)	0.0024 (9)	−0.0031 (8)	0.0008 (8)
C14	0.0254 (10)	0.0269 (10)	0.0239 (10)	0.0034 (9)	0.0004 (8)	0.0015 (7)
O1	0.0270 (8)	0.0395 (8)	0.0278 (8)	−0.0060 (8)	−0.0012 (6)	0.0043 (6)
O2	0.0333 (9)	0.0601 (11)	0.0331 (9)	0.0018 (8)	0.0071 (7)	0.0172 (8)
O3	0.0247 (8)	0.0405 (8)	0.0237 (7)	−0.0008 (7)	−0.0030 (6)	0.0052 (6)
O4	0.0258 (8)	0.0435 (9)	0.0269 (7)	−0.0053 (7)	−0.0021 (6)	0.0109 (6)
O5	0.0355 (8)	0.0468 (9)	0.0252 (8)	0.0033 (8)	0.0003 (7)	0.0124 (6)
O6	0.0395 (9)	0.0417 (9)	0.0320 (9)	0.0101 (8)	0.0094 (7)	0.0110 (7)
N1	0.0250 (9)	0.0321 (9)	0.0216 (9)	−0.0023 (8)	0.0001 (7)	0.0028 (7)

Geometric parameters (Å, º)

C1—C2	1.390 (3)	C10—N1	1.480 (3)
C1—C6	1.391 (3)	C10—H12A	0.96
C1—H1	0.9741	C10—H12B	0.96
C2—C3	1.380 (4)	C10—H12C	0.96
C2—H2	1.0536	C11—O2	1.232 (3)
C3—C4	1.378 (4)	C11—O3	1.293 (3)
C3—H3	0.9928	C11—C12	1.491 (3)
C4—C5	1.393 (3)	C12—C13	1.338 (3)
C4—H4	0.9809	C12—H13	0.9323
C5—C6	1.389 (3)	C13—C14	1.494 (3)
C5—H5	0.9305	C13—H14	0.9439
C6—C7	1.521 (3)	C14—O5	1.233 (2)
C7—O1	1.413 (3)	C14—O4	1.289 (3)
C7—C8	1.533 (3)	O1—H6	0.89 (4)
C7—H7	1.0297	O3—H15	1.4617
C8—N1	1.504 (3)	O4—H15	0.9696
C8—C9	1.520 (3)	O6—H16	0.9374
C8—H8	1.0172	O6—H17	0.83 (3)
C9—H9A	0.96	N1—H10	0.99 (2)
C9—H9B	0.96	N1—H11	0.94 (3)
C9—H9C	0.96
C2—C1—C6	120.7 (2)	H9A—C9—H9B	109.5
C2—C1—H1	117	C8—C9—H9C	109.5
C6—C1—H1	121.9	H9A—C9—H9C	109.5
C3—C2—C1	119.9 (2)	H9B—C9—H9C	109.5
C3—C2—H2	127.2	N1—C10—H12A	109.5
C1—C2—H2	112.7	N1—C10—H12B	109.5
C4—C3—C2	120.1 (2)	H12A—C10—H12B	109.5
C4—C3—H3	117.7	N1—C10—H12C	109.5
C2—C3—H3	122.2	H12A—C10—H12C	109.5
C3—C4—C5	120.1 (2)	H12B—C10—H12C	109.5
C3—C4—H4	126.7	O2—C11—O3	121.8 (2)
C5—C4—H4	113.2	O2—C11—C12	118.6 (2)
C6—C5—C4	120.5 (2)	O3—C11—C12	119.57 (18)
C6—C5—H5	121.9	C13—C12—C11	130.9 (2)
C4—C5—H5	117.1	C13—C12—H13	114.8
C5—C6—C1	118.74 (19)	C11—C12—H13	114.1
C5—C6—C7	120.94 (19)	C12—C13—C14	129.9 (2)
C1—C6—C7	120.32 (18)	C12—C13—H14	113.1
O1—C7—C6	113.13 (17)	C14—C13—H14	117
O1—C7—C8	106.96 (16)	O5—C14—O4	121.0 (2)
C6—C7—C8	110.71 (16)	O5—C14—C13	118.24 (19)
O1—C7—H7	110.8	O4—C14—C13	120.73 (16)
C6—C7—H7	105.4	C7—O1—H6	109 (2)
C8—C7—H7	109.8	C11—O3—H15	110.7
N1—C8—C9	106.82 (17)	C14—O4—H15	110.4
N1—C8—C7	109.09 (16)	H16—O6—H17	99.2
C9—C8—C7	113.32 (18)	C10—N1—C8	116.47 (16)
N1—C8—H8	109.4	C10—N1—H10	108.0 (14)
C9—C8—H8	108.8	C8—N1—H10	109.9 (14)
C7—C8—H8	109.4	C10—N1—H11	113.4 (16)
C8—C9—H9A	109.5	C8—N1—H11	108.2 (15)
C8—C9—H9B	109.5	H10—N1—H11	100 (2)
C6—C1—C2—C3	0.1 (3)	O1—C7—C8—N1	−54.0 (2)
C1—C2—C3—C4	−0.6 (4)	C6—C7—C8—N1	−177.67 (16)
C2—C3—C4—C5	0.7 (4)	O1—C7—C8—C9	64.9 (2)
C3—C4—C5—C6	−0.2 (3)	C6—C7—C8—C9	−58.8 (2)
C4—C5—C6—C1	−0.3 (3)	O2—C11—C12—C13	176.7 (2)
C4—C5—C6—C7	179.53 (19)	O3—C11—C12—C13	−2.6 (4)
C2—C1—C6—C5	0.3 (3)	C11—C12—C13—C14	−0.4 (4)
C2—C1—C6—C7	−179.48 (19)	C12—C13—C14—O5	−173.1 (2)
C5—C6—C7—O1	−17.1 (3)	C12—C13—C14—O4	6.7 (4)
C1—C6—C7—O1	162.66 (19)	C9—C8—N1—C10	176.4 (2)
C5—C6—C7—C8	102.9 (2)	C7—C8—N1—C10	−60.8 (2)
C1—C6—C7—C8	−77.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H6···O6^i	0.89 (4)	1.84 (4)	2.725 (2)	174 (3)
N1—H10···O3^ii	0.99 (2)	1.82 (3)	2.808 (2)	174 (2)
N1—H10···O2^ii	0.99 (2)	2.62 (3)	3.216 (3)	118.9 (18)
N1—H11···O2^iii	0.94 (3)	1.93 (3)	2.844 (2)	165 (2)
O6—H17···O5^iv	0.83 (3)	2.01 (3)	2.755 (2)	149 (3)

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

(EPHEMALO) (1R, 2S)-(-)-ephedrine malonate

Crystal data

C11H17NO3	F(000) = 468
Mr = 217.26	Dx = 1.235 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 7336 reflections
a = 15.1190 (14) Å	θ = 1.0–27.5°
b = 5.7840 (7) Å	µ = 0.09 mm^−1
c = 13.8788 (15) Å	T = 150 K
β = 105.765 (7)°	Needle, colourless
V = 1168.0 (2) Å^3	0.3 × 0.05 × 0.05 mm
Z = 4

Data collection

KappaCCD diffractometer	1448 independent reflections
Radiation source: Enraf Nonius FR590	937 reflections with I > 2σ(I)
Graphite monochromator	θmax = 27.5°, θmin = 2.8°
CCD rotation images, thick slices scans	h = −19→19
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	k = −6→7
Tmin = 0.987, Tmax = 1.021	l = −17→14
4107 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.3178P] where P = (Fo^2 + 2Fc^2)/3
1448 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.15 e Å^−3
1 restraint	Δρmin = −0.23 e Å^−3

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	Occ. (<1)
C1	0.3002 (3)	0.9664 (8)	0.1316 (3)	0.0496 (10)
H1	0.262 (3)	0.835 (8)	0.147 (3)	0.06*
C2	0.3336 (3)	0.9584 (9)	0.0474 (3)	0.0569 (11)
H2	0.318 (3)	0.823 (9)	0.004 (3)	0.068*
C3	0.3865 (3)	1.1377 (8)	0.0280 (3)	0.0564 (12)
H3	0.411 (3)	1.125 (8)	−0.030 (3)	0.068*
C4	0.4078 (3)	1.3199 (8)	0.0924 (3)	0.0561 (11)
H4	0.447 (3)	1.467 (8)	0.080 (3)	0.067*
C5	0.3747 (3)	1.3314 (7)	0.1768 (3)	0.0479 (10)
H5	0.389 (3)	1.459 (8)	0.224 (3)	0.057*
C6	0.3201 (2)	1.1523 (7)	0.1964 (3)	0.0421 (9)
C7	0.2841 (3)	1.1662 (6)	0.2886 (3)	0.0408 (9)
H7	0.339 (3)	1.240 (7)	0.347 (3)	0.049*
C8	0.2022 (3)	1.3267 (7)	0.2733 (3)	0.0433 (9)
H8	0.217 (2)	1.480 (8)	0.253 (3)	0.052*
C9	0.1149 (2)	1.2277 (9)	0.2038 (3)	0.0580 (11)
H9A	0.0957	1.0953	0.2346	0.087*
H9B	0.1264	1.1825	0.1418	0.087*
H9C	0.0674	1.3428	0.191	0.087*
C10	0.1129 (3)	1.5373 (9)	0.3772 (4)	0.0576 (11)
H12A	0.119 (3)	1.681 (9)	0.340 (3)	0.069*
H12B	0.052 (3)	1.469 (8)	0.340 (3)	0.069*
H12C	0.120 (3)	1.574 (9)	0.446 (3)	0.069*
C11	−0.0851 (2)	1.0927 (7)	0.4610 (3)	0.0429 (9)
C12	0	0.9540 (12)	0.5	0.087 (2)
H13	0.0082	0.8549	0.4467	0.104*	0.5
H14	−0.0082	0.8549	0.5533	0.104*	0.5
N1	0.1890 (2)	1.3749 (6)	0.3743 (2)	0.0432 (8)
H10	0.243 (3)	1.436 (7)	0.414 (3)	0.052*
H11	0.175 (3)	1.240 (8)	0.404 (3)	0.052*
O1	0.25754 (19)	0.9501 (5)	0.31847 (19)	0.0498 (7)
H6	0.305 (3)	0.875 (8)	0.341 (3)	0.06*
O2	−0.15250 (16)	1.0494 (5)	0.49529 (17)	0.0498 (7)
O3	−0.08517 (19)	1.2321 (7)	0.3944 (2)	0.0739 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.055 (2)	0.045 (2)	0.054 (2)	−0.002 (2)	0.0234 (18)	−0.002 (2)
C2	0.065 (3)	0.057 (3)	0.053 (2)	0.005 (2)	0.022 (2)	−0.011 (2)
C3	0.047 (2)	0.077 (3)	0.053 (2)	0.000 (2)	0.0252 (18)	−0.002 (2)
C4	0.045 (2)	0.070 (3)	0.060 (2)	−0.011 (2)	0.0251 (18)	−0.002 (2)
C5	0.047 (2)	0.053 (3)	0.046 (2)	−0.0041 (19)	0.0179 (17)	−0.0036 (19)
C6	0.0364 (19)	0.047 (2)	0.0445 (19)	−0.0022 (17)	0.0143 (15)	0.0007 (18)
C7	0.043 (2)	0.040 (2)	0.0434 (19)	−0.0051 (17)	0.0182 (16)	−0.0004 (17)
C8	0.042 (2)	0.046 (2)	0.0452 (19)	−0.0031 (17)	0.0172 (15)	0.0020 (18)
C9	0.042 (2)	0.080 (3)	0.052 (2)	0.000 (2)	0.0140 (18)	−0.002 (2)
C10	0.051 (2)	0.052 (3)	0.078 (3)	0.005 (2)	0.032 (2)	−0.002 (2)
C11	0.040 (2)	0.045 (2)	0.0436 (18)	0.0003 (17)	0.0117 (15)	−0.0077 (18)
C12	0.034 (3)	0.044 (4)	0.174 (7)	0	0.012 (4)	0
N1	0.0378 (17)	0.0461 (19)	0.0502 (18)	−0.0069 (16)	0.0194 (13)	−0.0019 (16)
O1	0.0497 (16)	0.0456 (18)	0.0582 (16)	−0.0010 (13)	0.0213 (13)	0.0075 (13)
O2	0.0431 (15)	0.0563 (16)	0.0555 (14)	−0.0029 (13)	0.0225 (12)	−0.0069 (14)
O3	0.0509 (17)	0.104 (3)	0.0693 (18)	−0.0005 (19)	0.0206 (14)	0.028 (2)

Geometric parameters (Å, º)

C1—C6	1.382 (5)	C8—H8	0.97 (5)
C1—C2	1.395 (5)	C9—H9A	0.96
C1—H1	1.01 (4)	C9—H9B	0.96
C2—C3	1.380 (6)	C9—H9C	0.96
C2—H2	0.98 (5)	C10—N1	1.494 (5)
C3—C4	1.363 (6)	C10—H12A	0.99 (5)
C3—H3	0.98 (4)	C10—H12B	1.00 (5)
C4—C5	1.394 (5)	C10—H12C	0.96 (4)
C4—H4	1.08 (5)	C11—O3	1.227 (5)
C5—C6	1.397 (5)	C11—O2	1.261 (4)
C5—H5	0.97 (4)	C11—C12	1.488 (5)
C6—C7	1.522 (5)	C12—C11^i	1.488 (5)
C7—O1	1.409 (4)	C12—H13	0.97
C7—C8	1.516 (5)	C12—H14	0.97
C7—H7	1.08 (4)	N1—H10	0.92 (4)
C8—N1	1.496 (5)	N1—H11	0.94 (4)
C8—C9	1.519 (5)	O1—H6	0.83 (4)
C6—C1—C2	120.5 (4)	C9—C8—H8	113 (2)
C6—C1—H1	119 (2)	C8—C9—H9A	109.5
C2—C1—H1	121 (2)	C8—C9—H9B	109.5
C3—C2—C1	120.0 (4)	H9A—C9—H9B	109.5
C3—C2—H2	122 (2)	C8—C9—H9C	109.5
C1—C2—H2	118 (2)	H9A—C9—H9C	109.5
C4—C3—C2	120.0 (3)	H9B—C9—H9C	109.5
C4—C3—H3	122 (3)	N1—C10—H12A	109 (2)
C2—C3—H3	118 (3)	N1—C10—H12B	110 (3)
C3—C4—C5	120.9 (4)	H12A—C10—H12B	105 (4)
C3—C4—H4	123 (2)	N1—C10—H12C	107 (3)
C5—C4—H4	116 (2)	H12A—C10—H12C	110 (4)
C4—C5—C6	119.6 (4)	H12B—C10—H12C	115 (3)
C4—C5—H5	123 (2)	O3—C11—O2	125.4 (3)
C6—C5—H5	117 (2)	O3—C11—C12	116.8 (3)
C1—C6—C5	119.1 (3)	O2—C11—C12	117.6 (3)
C1—C6—C7	121.6 (3)	C11—C12—C11^i	114.8 (6)
C5—C6—C7	119.3 (3)	C11—C12—H13	108.6
O1—C7—C8	107.3 (3)	C11^i—C12—H13	108.6
O1—C7—C6	113.3 (3)	C11—C12—H14	108.6
C8—C7—C6	112.3 (3)	C11^i—C12—H14	108.6
O1—C7—H7	111 (2)	H13—C12—H14	107.6
C8—C7—H7	107 (2)	C10—N1—C8	116.3 (3)
C6—C7—H7	106.1 (18)	C10—N1—H10	108 (2)
N1—C8—C7	107.1 (3)	C8—N1—H10	108 (2)
N1—C8—C9	110.6 (3)	C10—N1—H11	104 (2)
C7—C8—C9	113.2 (4)	C8—N1—H11	111 (2)
N1—C8—H8	101 (2)	H10—N1—H11	109 (3)
C7—C8—H8	111 (2)	C7—O1—H6	107 (3)
C6—C1—C2—C3	−0.4 (7)	C1—C6—C7—C8	−101.8 (4)
C1—C2—C3—C4	1.5 (7)	C5—C6—C7—C8	78.4 (4)
C2—C3—C4—C5	−1.8 (7)	O1—C7—C8—N1	69.5 (4)
C3—C4—C5—C6	0.9 (7)	C6—C7—C8—N1	−165.3 (3)
C2—C1—C6—C5	−0.5 (6)	O1—C7—C8—C9	−52.6 (4)
C2—C1—C6—C7	179.7 (4)	C6—C7—C8—C9	72.5 (4)
C4—C5—C6—C1	0.2 (6)	O3—C11—C12—C11^i	56.6 (3)
C4—C5—C6—C7	−180.0 (4)	O2—C11—C12—C11^i	−126.9 (3)
C1—C6—C7—O1	19.9 (5)	C7—C8—N1—C10	178.1 (3)
C5—C6—C7—O1	−159.9 (3)	C9—C8—N1—C10	−58.1 (5)

Symmetry code: (i) −x, y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O2^ii	0.92 (4)	1.80 (4)	2.719 (4)	178 (3)
N1—H11···O2^i	0.94 (4)	1.88 (4)	2.769 (4)	158 (4)
O1—H6···O3^iii	0.83 (4)	1.82 (5)	2.645 (4)	175 (5)

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

(EPHEMESY) (1R, 2S)-(-)-ephedrine mesylate

Crystal data

C11H19NO4S	F(000) = 560
Mr = 261.33	Dx = 1.329 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 32320 reflections
a = 14.287 (2) Å	θ = 1.0–27.5°
b = 6.1075 (7) Å	µ = 0.25 mm^−1
c = 14.993 (2) Å	T = 150 K
β = 93.211 (6)°	Needle, colourless
V = 1306.3 (3) Å^3	0.3 × 0.05 × 0.05 mm
Z = 4

Data collection

KappaCCD diffractometer	2236 independent reflections
Radiation source: Enraf Nonius FR590	1751 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −13→14
Tmin = 0.984, Tmax = 1.017	k = −7→7
3231 measured reflections	l = −19→13

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0349P)^2 + 1.5263P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.002
2236 reflections	Δρmax = 0.20 e Å^−3
179 parameters	Δρmin = −0.33 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (14)

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
C1	0.7331 (3)	1.1379 (8)	0.8743 (3)	0.0452 (11)
H1	0.779 (3)	1.260 (8)	0.859 (3)	0.054*
C2	0.6799 (4)	1.1472 (10)	0.9496 (3)	0.0566 (13)
H2	0.6846	1.2684	0.9871	0.068*
C3	0.6207 (3)	0.9779 (13)	0.9686 (3)	0.0551 (12)
H3	0.5864	0.9835	1.0194	0.066*
C4	0.6122 (4)	0.8000 (10)	0.9122 (3)	0.0546 (13)
H4	0.569 (3)	0.663 (9)	0.932 (3)	0.066*
C5	0.6645 (3)	0.7875 (9)	0.8372 (3)	0.0446 (11)
H5	0.657 (3)	0.652 (9)	0.798 (3)	0.054*
C6	0.7257 (2)	0.9583 (9)	0.8181 (2)	0.0344 (8)
C7	0.7853 (3)	0.9374 (7)	0.7377 (2)	0.0322 (9)
H7	0.743 (3)	0.883 (6)	0.681 (2)	0.039*
C8	0.8638 (3)	0.7697 (8)	0.7542 (3)	0.0360 (10)
H8	0.836 (3)	0.631 (8)	0.768 (2)	0.043*
C9	0.9381 (3)	0.8471 (9)	0.8238 (3)	0.0492 (12)
H9A	0.9828	0.7319	0.836	0.074*
H9B	0.9089	0.8851	0.8778	0.074*
H9C	0.9696	0.973	0.8016	0.074*
C10	0.9741 (3)	0.5363 (7)	0.6674 (3)	0.0498 (12)
H12A	1.0258	0.5606	0.71	0.075*
H12B	0.9973	0.519	0.609	0.075*
H12C	0.9411	0.4063	0.6832	0.075*
C11	0.6427 (3)	0.6881 (8)	0.5094 (3)	0.0436 (12)
H13A	0.5879	0.6888	0.4693	0.065*
H13B	0.6976	0.6728	0.4758	0.065*
H13C	0.6461	0.823	0.5423	0.065*
N1	0.9090 (3)	0.7283 (6)	0.6675 (2)	0.0351 (8)
H10	0.858 (3)	0.707 (7)	0.623 (3)	0.042*
H11	0.937 (3)	0.836 (8)	0.653 (3)	0.042*
O1	0.8263 (2)	1.1391 (5)	0.7140 (2)	0.0445 (7)
H6	0.8814	1.1414	0.7324	0.067*
O2	0.72468 (18)	0.4740 (6)	0.63878 (15)	0.0453 (7)
O3	0.5562 (2)	0.5129 (5)	0.63647 (18)	0.0493 (9)
O4	0.6274 (2)	0.2689 (5)	0.5309 (2)	0.0465 (8)
S1	0.63637 (6)	0.46809 (17)	0.58403 (5)	0.0330 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.048 (3)	0.038 (3)	0.050 (3)	−0.004 (2)	0.007 (2)	−0.005 (2)
C2	0.054 (3)	0.064 (4)	0.052 (3)	0.008 (3)	0.006 (2)	−0.016 (3)
C3	0.037 (3)	0.085 (4)	0.045 (2)	−0.002 (3)	0.0106 (17)	−0.005 (3)
C4	0.044 (3)	0.069 (4)	0.052 (3)	−0.015 (3)	0.011 (2)	−0.001 (3)
C5	0.043 (3)	0.049 (3)	0.042 (2)	−0.011 (2)	0.0063 (19)	−0.003 (2)
C6	0.030 (2)	0.040 (2)	0.0338 (17)	0.005 (2)	0.0016 (13)	0.004 (2)
C7	0.029 (2)	0.032 (3)	0.0352 (19)	−0.0051 (19)	0.0013 (14)	−0.0007 (18)
C8	0.035 (3)	0.036 (3)	0.038 (2)	−0.002 (2)	0.0100 (17)	0.0046 (19)
C9	0.042 (3)	0.068 (3)	0.036 (2)	0.001 (2)	−0.0061 (19)	−0.001 (2)
C10	0.042 (3)	0.035 (3)	0.074 (3)	0.0044 (18)	0.014 (2)	0.002 (2)
C11	0.043 (3)	0.047 (3)	0.041 (2)	−0.003 (2)	0.0013 (19)	0.007 (2)
N1	0.035 (2)	0.033 (2)	0.0371 (19)	0.0018 (15)	0.0039 (14)	0.0005 (14)
O1	0.0397 (19)	0.0435 (19)	0.0509 (17)	−0.0038 (15)	0.0072 (14)	0.0082 (15)
O2	0.0425 (16)	0.0421 (16)	0.0494 (15)	0.0016 (17)	−0.0141 (11)	−0.0024 (17)
O3	0.0441 (19)	0.053 (3)	0.0530 (16)	−0.0014 (15)	0.0249 (13)	−0.0032 (14)
O4	0.047 (2)	0.0388 (19)	0.0534 (19)	−0.0064 (15)	0.0042 (14)	−0.0155 (14)
S1	0.0306 (5)	0.0317 (5)	0.0370 (5)	−0.0007 (6)	0.0047 (3)	−0.0012 (5)

Geometric parameters (Å, º)

C1—C6	1.384 (6)	C9—H9A	0.96
C1—C2	1.398 (6)	C9—H9B	0.96
C1—H1	1.02 (5)	C9—H9C	0.96
C2—C3	1.376 (8)	C10—N1	1.497 (5)
C2—H2	0.93	C10—H12A	0.96
C3—C4	1.378 (8)	C10—H12B	0.96
C3—H3	0.93	C10—H12C	0.96
C4—C5	1.386 (6)	C11—S1	1.754 (4)
C4—H4	1.09 (5)	C11—H13A	0.96
C5—C6	1.402 (7)	C11—H13B	0.96
C5—H5	1.02 (5)	C11—H13C	0.96
C6—C7	1.519 (5)	N1—H10	0.97 (4)
C7—O1	1.418 (5)	N1—H11	0.81 (5)
C7—C8	1.528 (6)	O1—H6	0.82
C7—H7	1.07 (4)	O2—S1	1.467 (2)
C8—N1	1.505 (5)	O3—S1	1.451 (3)
C8—C9	1.522 (6)	O4—S1	1.456 (3)
C8—H8	0.97 (5)
C6—C1—C2	119.9 (4)	C8—C9—H9B	109.5
C6—C1—H1	118 (3)	H9A—C9—H9B	109.5
C2—C1—H1	122 (3)	C8—C9—H9C	109.5
C3—C2—C1	120.3 (5)	H9A—C9—H9C	109.5
C3—C2—H2	119.8	H9B—C9—H9C	109.5
C1—C2—H2	119.8	N1—C10—H12A	109.5
C2—C3—C4	120.0 (4)	N1—C10—H12B	109.5
C2—C3—H3	120	H12A—C10—H12B	109.5
C4—C3—H3	120	N1—C10—H12C	109.5
C3—C4—C5	120.6 (5)	H12A—C10—H12C	109.5
C3—C4—H4	118 (2)	H12B—C10—H12C	109.5
C5—C4—H4	121 (3)	S1—C11—H13A	109.5
C4—C5—C6	119.7 (5)	S1—C11—H13B	109.5
C4—C5—H5	118 (3)	H13A—C11—H13B	109.5
C6—C5—H5	122 (3)	S1—C11—H13C	109.5
C1—C6—C5	119.5 (3)	H13A—C11—H13C	109.5
C1—C6—C7	121.5 (4)	H13B—C11—H13C	109.5
C5—C6—C7	118.9 (4)	C10—N1—C8	115.4 (3)
O1—C7—C6	112.5 (4)	C10—N1—H10	109 (3)
O1—C7—C8	108.3 (3)	C8—N1—H10	106 (2)
C6—C7—C8	111.5 (3)	C10—N1—H11	109 (3)
O1—C7—H7	107 (2)	C8—N1—H11	110 (3)
C6—C7—H7	110 (2)	H10—N1—H11	107 (4)
C8—C7—H7	107 (2)	C7—O1—H6	109.5
N1—C8—C9	109.1 (4)	O3—S1—O4	113.94 (19)
N1—C8—C7	108.6 (3)	O3—S1—O2	111.87 (16)
C9—C8—C7	112.4 (4)	O4—S1—O2	111.9 (2)
N1—C8—H8	104 (2)	O3—S1—C11	105.8 (2)
C9—C8—H8	114 (2)	O4—S1—C11	107.31 (18)
C7—C8—H8	108 (3)	O2—S1—C11	105.3 (2)
C8—C9—H9A	109.5
C6—C1—C2—C3	0.5 (8)	C5—C6—C7—O1	165.9 (4)
C1—C2—C3—C4	−1.3 (8)	C1—C6—C7—C8	105.4 (5)
C2—C3—C4—C5	1.4 (9)	C5—C6—C7—C8	−72.3 (5)
C3—C4—C5—C6	−0.7 (8)	O1—C7—C8—N1	−65.5 (4)
C2—C1—C6—C5	0.2 (7)	C6—C7—C8—N1	170.2 (4)
C2—C1—C6—C7	−177.4 (4)	O1—C7—C8—C9	55.3 (4)
C4—C5—C6—C1	−0.1 (7)	C6—C7—C8—C9	−68.9 (5)
C4—C5—C6—C7	177.6 (4)	C9—C8—N1—C10	68.9 (5)
C1—C6—C7—O1	−16.4 (5)	C7—C8—N1—C10	−168.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O4^i	0.97 (4)	2.36 (4)	3.002 (5)	124 (3)
N1—H11···O3^ii	0.81 (5)	2.04 (5)	2.788 (5)	153 (5)

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

(EPHENITR) (1R, 2S)-(-)-ephedrine nitrate

Crystal data

C10H14N2O4	F(000) = 244
Mr = 228.25	Dx = 1.285 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4151 reflections
a = 5.5309 (4) Å	θ = 1.0–27.5°
b = 6.8501 (6) Å	µ = 0.1 mm^−1
c = 15.6906 (13) Å	T = 150 K
β = 97.243 (6)°	Plate, yellow
V = 589.73 (8) Å^3	0.2 × 0.2 × 0.05 mm
Z = 2

Data collection

KappaCCD diffractometer	1274 independent reflections
Radiation source: Enraf Nonius FR590	991 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −5→7
Tmin = 0.951, Tmax = 1.041	k = −6→8
2914 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0466P)^2] where P = (Fo^2 + 2Fc^2)/3
1274 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.17 e Å^−3
1 restraint	Δρmin = −0.23 e Å^−3

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
C1	−0.0329 (6)	0.5459 (5)	0.3402 (2)	0.0404 (7)
H1	−0.169 (7)	0.565 (6)	0.299 (2)	0.049*
C2	−0.0436 (7)	0.6236 (6)	0.4211 (2)	0.0498 (8)
H2	−0.185 (7)	0.693 (7)	0.435 (2)	0.06*
C3	0.1510 (6)	0.6036 (6)	0.4847 (2)	0.0505 (9)
H3	0.140 (6)	0.654 (7)	0.542 (2)	0.061*
C4	0.3562 (7)	0.5038 (6)	0.4677 (2)	0.0518 (9)
H4	0.483 (7)	0.489 (7)	0.511 (3)	0.062*
C5	0.3679 (6)	0.4258 (5)	0.3870 (2)	0.0432 (8)
H5	0.516 (6)	0.353 (7)	0.3714 (19)	0.052*
C6	0.1751 (5)	0.4460 (4)	0.32202 (19)	0.0364 (7)
H6	0.456 (6)	0.437 (7)	0.188 (2)	0.044*
C7	0.1859 (5)	0.3675 (5)	0.23264 (18)	0.0332 (6)
H7	0.100 (5)	0.462 (6)	0.196 (2)	0.04*
C8	0.0613 (5)	0.1688 (5)	0.21980 (18)	0.0365 (7)
H8	−0.111 (5)	0.190 (6)	0.2266 (18)	0.044*
C9	0.1802 (8)	0.0130 (6)	0.2798 (2)	0.0510 (9)
H9A	0.360 (7)	0.018 (7)	0.280 (2)	0.061*
H9B	0.108 (6)	−0.114 (7)	0.268 (2)	0.061*
H9C	0.136 (6)	0.038 (7)	0.343 (2)	0.061*
C10	−0.0222 (6)	0.2406 (5)	0.0604 (2)	0.0439 (8)
H12A	−0.1764	0.2913	0.0721	0.066*
H12B	−0.0422	0.1754	0.0058	0.066*
H12C	0.0918	0.3459	0.0591	0.066*
N1	0.0715 (5)	0.0995 (4)	0.12897 (15)	0.0363 (6)
H10	0.244 (6)	0.070 (5)	0.1250 (19)	0.044*
H11	−0.016 (6)	0.002 (7)	0.121 (2)	0.044*
N2	0.5696 (4)	0.8008 (4)	0.11488 (15)	0.0366 (6)
O1	0.4272 (3)	0.3458 (4)	0.21190 (14)	0.0403 (5)
O2	0.7798 (4)	0.7339 (4)	0.12860 (14)	0.0479 (6)
O3	0.3895 (4)	0.7037 (4)	0.12808 (14)	0.0500 (6)
O4	0.5408 (4)	0.9729 (4)	0.08800 (15)	0.0537 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0421 (16)	0.0297 (18)	0.0500 (18)	−0.0046 (14)	0.0077 (14)	−0.0037 (14)
C2	0.055 (2)	0.035 (2)	0.064 (2)	−0.0082 (16)	0.0229 (17)	−0.0081 (16)
C3	0.062 (2)	0.045 (2)	0.0456 (18)	−0.0174 (18)	0.0110 (16)	−0.0052 (15)
C4	0.056 (2)	0.051 (2)	0.0473 (18)	−0.0136 (18)	0.0021 (15)	0.0017 (17)
C5	0.0448 (16)	0.036 (2)	0.0488 (18)	−0.0062 (14)	0.0056 (14)	0.0030 (14)
C6	0.0400 (15)	0.0230 (17)	0.0463 (16)	−0.0087 (12)	0.0056 (13)	0.0054 (12)
C7	0.0344 (13)	0.0215 (15)	0.0430 (15)	−0.0013 (13)	0.0025 (11)	0.0035 (12)
C8	0.0406 (16)	0.0265 (17)	0.0427 (17)	−0.0068 (13)	0.0067 (13)	0.0023 (13)
C9	0.075 (2)	0.026 (2)	0.050 (2)	−0.0067 (17)	0.0003 (17)	0.0086 (15)
C10	0.0523 (17)	0.0343 (19)	0.0445 (16)	−0.0021 (15)	0.0036 (13)	0.0016 (14)
N1	0.0373 (14)	0.0244 (15)	0.0468 (15)	−0.0035 (11)	0.0033 (11)	0.0027 (11)
N2	0.0384 (13)	0.0274 (15)	0.0449 (13)	−0.0016 (11)	0.0086 (10)	0.0027 (11)
O1	0.0392 (11)	0.0291 (14)	0.0534 (13)	−0.0019 (9)	0.0089 (9)	0.0032 (9)
O2	0.0390 (11)	0.0423 (14)	0.0616 (13)	0.0056 (11)	0.0033 (9)	0.0008 (11)
O3	0.0453 (11)	0.0386 (14)	0.0673 (14)	−0.0071 (11)	0.0115 (10)	0.0110 (11)
O4	0.0479 (13)	0.0296 (14)	0.0858 (17)	−0.0015 (11)	0.0162 (12)	0.0137 (12)

Geometric parameters (Å, º)

C1—C2	1.385 (5)	C8—C9	1.517 (5)
C1—C6	1.399 (4)	C8—H8	0.99 (3)
C1—H1	0.94 (4)	C9—H9A	0.99 (4)
C2—C3	1.379 (5)	C9—H9B	0.97 (5)
C2—H2	0.96 (4)	C9—H9C	1.06 (4)
C3—C4	1.379 (6)	C10—N1	1.490 (4)
C3—H3	0.97 (4)	C10—H12A	0.96
C4—C5	1.383 (5)	C10—H12B	0.96
C4—H4	0.91 (4)	C10—H12C	0.96
C5—C6	1.387 (4)	N1—H10	0.99 (3)
C5—H5	1.01 (4)	N1—H11	0.83 (4)
C6—C7	1.510 (4)	N2—O3	1.237 (3)
C7—O1	1.421 (3)	N2—O2	1.243 (3)
C7—C8	1.527 (4)	N2—O4	1.256 (3)
C7—H7	0.95 (4)	O1—H6	0.76 (4)
C8—N1	1.510 (4)
C2—C1—C6	120.4 (3)	C9—C8—C7	113.1 (3)
C2—C1—H1	117 (2)	N1—C8—H8	107.4 (17)
C6—C1—H1	123 (2)	C9—C8—H8	113 (2)
C3—C2—C1	120.4 (4)	C7—C8—H8	107 (2)
C3—C2—H2	118 (2)	C8—C9—H9A	109 (2)
C1—C2—H2	122 (2)	C8—C9—H9B	112 (2)
C2—C3—C4	119.7 (4)	H9A—C9—H9B	115 (4)
C2—C3—H3	120 (2)	C8—C9—H9C	109 (2)
C4—C3—H3	120 (2)	H9A—C9—H9C	110 (3)
C3—C4—C5	120.2 (3)	H9B—C9—H9C	101 (3)
C3—C4—H4	119 (3)	N1—C10—H12A	109.5
C5—C4—H4	121 (3)	N1—C10—H12B	109.5
C4—C5—C6	121.0 (3)	H12A—C10—H12B	109.5
C4—C5—H5	123.0 (17)	N1—C10—H12C	109.5
C6—C5—H5	116.1 (17)	H12A—C10—H12C	109.5
C5—C6—C1	118.4 (3)	H12B—C10—H12C	109.5
C5—C6—C7	122.1 (3)	C10—N1—C8	115.3 (3)
C1—C6—C7	119.6 (3)	C10—N1—H10	110 (2)
O1—C7—C6	113.5 (2)	C8—N1—H10	106.1 (18)
O1—C7—C8	107.3 (2)	C10—N1—H11	106 (2)
C6—C7—C8	111.7 (2)	C8—N1—H11	108 (2)
O1—C7—H7	110.2 (18)	H10—N1—H11	112 (3)
C6—C7—H7	104 (2)	O3—N2—O2	121.9 (3)
C8—C7—H7	110 (2)	O3—N2—O4	119.4 (2)
N1—C8—C9	107.4 (3)	O2—N2—O4	118.7 (2)
N1—C8—C7	109.6 (2)	C7—O1—H6	107 (3)
C6—C1—C2—C3	0.1 (5)	C1—C6—C7—O1	154.8 (3)
C1—C2—C3—C4	−0.7 (5)	C5—C6—C7—C8	97.6 (3)
C2—C3—C4—C5	0.7 (5)	C1—C6—C7—C8	−83.7 (3)
C3—C4—C5—C6	−0.1 (5)	O1—C7—C8—N1	−56.5 (3)
C4—C5—C6—C1	−0.5 (5)	C6—C7—C8—N1	178.5 (2)
C4—C5—C6—C7	178.2 (3)	O1—C7—C8—C9	63.3 (4)
C2—C1—C6—C5	0.5 (4)	C6—C7—C8—C9	−61.6 (4)
C2—C1—C6—C7	−178.2 (3)	C9—C8—N1—C10	−176.0 (3)
C5—C6—C7—O1	−23.9 (4)	C7—C8—N1—C10	−52.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O4^i	0.99 (3)	1.93 (3)	2.885 (4)	164 (3)
N1—H10···N2^i	0.99 (3)	2.59 (4)	3.461 (4)	147 (3)
N1—H10···O3^i	0.99 (3)	2.63 (4)	3.233 (4)	120 (3)
N1—H11···O2^ii	0.83 (4)	2.16 (4)	2.978 (4)	168 (3)
N1—H11···O4^ii	0.83 (4)	2.45 (3)	3.051 (3)	130 (3)
N1—H11···N2^ii	0.83 (4)	2.66 (4)	3.433 (4)	155 (3)

Symmetry codes: (i) x, y−1, z; (ii) x−1, y−1, z.

(EPHEPHOS) (1R, 2S)-(-)-ephedrine dihydrogen phosphate

Crystal data

C10H16NO5P	F(000) = 560
Mr = 263.22	Dx = 1.394 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 6301 reflections
a = 14.6992 (10) Å	θ = 1.0–27.5°
b = 5.6433 (4) Å	µ = 0.23 mm^−1
c = 15.2432 (14) Å	T = 150 K
β = 97.333 (3)°	Needle, colourless
V = 1254.11 (17) Å^3	0.25 × 0.05 × 0.05 mm
Z = 4

Data collection

KappaCCD diffractometer	2497 independent reflections
Radiation source: Enraf Nonius FR590	2110 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
CCD rotation images, thick slices scans	θmax = 27.4°, θmin = 2.8°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −18→14
Tmin = 0.954, Tmax = 1.056	k = −7→7
4138 measured reflections	l = −19→19

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.P)^2 + 2.2505P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.119	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.31 e Å^−3
2497 reflections	Δρmin = −0.37 e Å^−3
173 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.018 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.13 (15)

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
C1	0.3548 (2)	0.8180 (7)	0.6557 (2)	0.0289 (8)
H1	0.368 (2)	0.677 (7)	0.695 (3)	0.035*
C2	0.3993 (2)	0.8304 (7)	0.5802 (3)	0.0348 (9)
H2	0.443 (3)	0.695 (7)	0.567 (3)	0.042*
C3	0.3841 (2)	1.0262 (7)	0.5237 (3)	0.0338 (9)
H3	0.415 (3)	1.030 (8)	0.469 (3)	0.041*
C4	0.3254 (3)	1.2054 (8)	0.5432 (3)	0.0347 (9)
H4	0.316 (3)	1.336 (8)	0.505 (3)	0.042*
C5	0.2811 (3)	1.1901 (7)	0.6182 (3)	0.0324 (9)
H5	0.245 (3)	1.314 (8)	0.634 (3)	0.039*
C6	0.2953 (2)	0.9963 (7)	0.6750 (2)	0.0257 (8)
C7	0.2455 (2)	0.9729 (7)	0.7557 (2)	0.0276 (8)
H7	0.289 (2)	0.896 (7)	0.806 (3)	0.033*
C8	0.1622 (2)	0.8075 (6)	0.7381 (2)	0.0276 (8)
H8	0.178 (2)	0.651 (7)	0.710 (3)	0.033*
C9	0.0821 (3)	0.9185 (8)	0.6795 (3)	0.0356 (9)
H9A	0.0344	0.803	0.6664	0.053*
H9B	0.1023	0.972	0.6255	0.053*
H9C	0.059	1.0506	0.7097	0.053*
C10	0.05114 (14)	0.5858 (4)	0.8238 (2)	0.0334 (8)
H12A	−0.0016	0.6739	0.7984	0.05*
H12B	0.0434	0.54	0.8831	0.05*
H12C	0.0577	0.4467	0.7889	0.05*
O1	0.21329 (14)	1.1954 (4)	0.78344 (17)	0.0332 (7)
H6	0.2443	1.2363	0.8295	0.05*
N1	0.13475 (18)	0.7361 (6)	0.82548 (19)	0.0271 (7)
H10	0.182	0.6575	0.8557	0.033*
H11	0.126	0.8688	0.8561	0.033*
P1	0.36077 (5)	0.61493 (17)	0.95859 (6)	0.0249 (3)
O2	0.27240 (15)	0.4862 (4)	0.92661 (17)	0.0286 (6)
O3	0.40593 (15)	0.5393 (5)	1.04823 (16)	0.0311 (6)
O4	0.42669 (13)	0.5879 (3)	0.88673 (13)	0.0308 (6)
H13	0.4794	0.6171	0.9086	0.046*
O5	0.34129 (14)	0.8902 (3)	0.95827 (14)	0.0314 (6)
H14	0.3027	0.919	0.9911	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0271 (18)	0.036 (2)	0.0232 (19)	0.0031 (15)	0.0018 (14)	−0.0003 (16)
C2	0.0216 (17)	0.044 (2)	0.038 (2)	0.0020 (16)	0.0015 (16)	−0.0011 (18)
C3	0.0256 (18)	0.045 (2)	0.031 (2)	−0.0013 (16)	0.0019 (16)	0.0026 (17)
C4	0.032 (2)	0.041 (2)	0.030 (2)	−0.0018 (17)	0.0010 (16)	0.0056 (17)
C5	0.035 (2)	0.032 (2)	0.029 (2)	0.0043 (16)	0.0001 (16)	0.0014 (15)
C6	0.0198 (16)	0.0322 (19)	0.0251 (19)	−0.0011 (14)	0.0025 (14)	−0.0056 (15)
C7	0.0264 (18)	0.031 (2)	0.0242 (19)	0.0033 (14)	−0.0032 (15)	0.0000 (15)
C8	0.0314 (18)	0.031 (2)	0.0198 (17)	0.0016 (15)	0.0014 (14)	−0.0018 (15)
C9	0.035 (2)	0.045 (2)	0.024 (2)	0.0003 (18)	−0.0058 (16)	0.0007 (17)
C10	0.0246 (16)	0.036 (2)	0.039 (2)	−0.0006 (17)	0.0028 (14)	−0.0023 (18)
O1	0.0382 (15)	0.0339 (16)	0.0267 (14)	0.0014 (11)	0.0006 (11)	−0.0085 (10)
N1	0.0238 (14)	0.0313 (16)	0.0258 (16)	0.0041 (13)	0.0021 (12)	0.0004 (14)
P1	0.0185 (4)	0.0314 (5)	0.0241 (5)	0.0011 (4)	−0.0001 (3)	0.0011 (4)
O2	0.0214 (12)	0.0302 (14)	0.0333 (14)	−0.0010 (10)	−0.0001 (10)	−0.0031 (11)
O3	0.0220 (11)	0.0445 (17)	0.0265 (13)	0.0001 (10)	0.0009 (10)	0.0063 (11)
O4	0.0209 (10)	0.0472 (16)	0.0245 (12)	0.0027 (12)	0.0037 (9)	0.0008 (12)
O5	0.0318 (14)	0.0304 (14)	0.0321 (15)	0.0012 (11)	0.0042 (12)	−0.0016 (11)

Geometric parameters (Å, º)

C1—C6	1.389 (5)	C8—H8	1.02 (4)
C1—C2	1.397 (5)	C9—H9A	0.96
C1—H1	1.00 (4)	C9—H9B	0.96
C2—C3	1.401 (6)	C9—H9C	0.96
C2—H2	1.03 (4)	C10—N1	1.491 (4)
C3—C4	1.386 (6)	C10—H12A	0.96
C3—H3	1.00 (4)	C10—H12B	0.96
C4—C5	1.389 (5)	C10—H12C	0.96
C4—H4	0.94 (4)	O1—H6	0.82
C5—C6	1.393 (5)	N1—H10	0.9
C5—H5	0.93 (4)	N1—H11	0.9
C6—C7	1.515 (5)	P1—O3	1.503 (2)
C7—O1	1.425 (4)	P1—O2	1.514 (2)
C7—C8	1.536 (5)	P1—O4	1.5597 (18)
C7—H7	1.03 (4)	P1—O5	1.580 (2)
C8—N1	1.495 (4)	O4—H13	0.82
C8—C9	1.519 (5)	O5—H14	0.82
C6—C1—C2	120.8 (4)	C7—C8—H8	112 (2)
C6—C1—H1	123 (2)	C8—C9—H9A	109.5
C2—C1—H1	117 (2)	C8—C9—H9B	109.5
C1—C2—C3	119.5 (4)	H9A—C9—H9B	109.5
C1—C2—H2	119 (2)	C8—C9—H9C	109.5
C3—C2—H2	121 (2)	H9A—C9—H9C	109.5
C4—C3—C2	119.9 (4)	H9B—C9—H9C	109.5
C4—C3—H3	122 (3)	N1—C10—H12A	109.5
C2—C3—H3	118 (3)	N1—C10—H12B	109.5
C3—C4—C5	120.1 (4)	H12A—C10—H12B	109.5
C3—C4—H4	119 (3)	N1—C10—H12C	109.5
C5—C4—H4	121 (3)	H12A—C10—H12C	109.5
C4—C5—C6	120.8 (4)	H12B—C10—H12C	109.5
C4—C5—H5	121 (3)	C7—O1—H6	109.5
C6—C5—H5	118 (3)	C10—N1—C8	117.0 (3)
C1—C6—C5	119.0 (3)	C10—N1—H10	108.1
C1—C6—C7	119.4 (3)	C8—N1—H10	108.1
C5—C6—C7	121.6 (3)	C10—N1—H11	108.1
O1—C7—C6	112.2 (3)	C8—N1—H11	108.1
O1—C7—C8	107.4 (3)	H10—N1—H11	107.3
C6—C7—C8	111.6 (3)	O3—P1—O2	114.70 (15)
O1—C7—H7	110 (2)	O3—P1—O4	111.65 (13)
C6—C7—H7	109 (2)	O2—P1—O4	108.14 (13)
C8—C7—H7	106 (2)	O3—P1—O5	109.93 (14)
N1—C8—C9	111.0 (3)	O2—P1—O5	108.86 (13)
N1—C8—C7	108.0 (3)	O4—P1—O5	102.87 (11)
C9—C8—C7	113.1 (3)	P1—O4—H13	109.5
N1—C8—H8	104 (2)	P1—O5—H14	109.4
C9—C8—H8	108 (2)
C6—C1—C2—C3	0.5 (5)	C5—C6—C7—O1	−21.7 (4)
C1—C2—C3—C4	0.0 (6)	C1—C6—C7—C8	−79.5 (4)
C2—C3—C4—C5	−0.4 (6)	C5—C6—C7—C8	98.9 (4)
C3—C4—C5—C6	0.3 (6)	O1—C7—C8—N1	−73.6 (4)
C2—C1—C6—C5	−0.7 (5)	C6—C7—C8—N1	163.1 (3)
C2—C1—C6—C7	177.8 (3)	O1—C7—C8—C9	49.7 (4)
C4—C5—C6—C1	0.2 (5)	C6—C7—C8—C9	−73.7 (4)
C4—C5—C6—C7	−178.2 (3)	C9—C8—N1—C10	51.9 (4)
C1—C6—C7—O1	159.9 (3)	C7—C8—N1—C10	176.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O2	0.9	1.87	2.768 (4)	174
O4—H13···O3^i	0.82	1.78	2.547 (3)	154
O5—H14···O2^ii	0.82	1.81	2.630 (3)	174
N1—H11···O3^ii	0.9	1.86	2.699 (4)	155
O1—H6···O2^iii	0.82	2.05	2.780 (3)	148

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

(EPHEBISU) (1R, 2S)-(-)-ephedrine bisulfate

Crystal data

C10H18NO5S	F(000) = 560
Mr = 263.31	Dx = 1.44 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 22048 reflections
a = 30.9967 (17) Å	θ = 1.0–29.1°
b = 6.9861 (4) Å	µ = 0.28 mm^−1
c = 5.6170 (3) Å	T = 150 K
β = 93.354 (3)°	Needle, colourless
V = 1214.26 (12) Å^3	0.35 × 0.15 × 0.05 mm
Z = 4

Data collection

KappaCCD diffractometer	3183 independent reflections
Radiation source: Enraf Nonius FR590	1982 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
CCD rotation images, thick slices scans	θmax = 28.9°, θmin = 2.6°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −41→41
Tmin = 0.969, Tmax = 1.029	k = −9→9
10680 measured reflections	l = −7→7

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)] = 0.074	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0287P)^2 + 1.1389P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
3183 reflections	Δρmax = 0.31 e Å^−3
173 parameters	Δρmin = −0.37 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (12)

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
C1	0.69736 (14)	0.5950 (6)	0.8924 (7)	0.0284 (10)
H1	0.6776 (13)	0.639 (6)	1.015 (7)	0.034*
C2	0.74148 (14)	0.6077 (6)	0.9390 (8)	0.0273 (10)
H2	0.7516 (14)	0.667 (6)	1.073 (7)	0.033*
C3	0.76962 (14)	0.5381 (5)	0.7768 (7)	0.0275 (10)
H3	0.7993	0.5448	0.8102	0.033*
C4	0.75313 (13)	0.4582 (5)	0.5641 (7)	0.0249 (10)
H4	0.7720 (12)	0.428 (6)	0.442 (6)	0.03*
C5	0.70880 (13)	0.4471 (5)	0.5176 (7)	0.0243 (10)
H5	0.6974 (11)	0.404 (6)	0.368 (6)	0.029*
C6	0.68042 (13)	0.5124 (5)	0.6821 (7)	0.0236 (9)
C7	0.63223 (13)	0.4804 (5)	0.6424 (7)	0.0242 (9)
H7	0.6169	0.5885	0.7096	0.029*
C8	0.61885 (12)	0.2950 (5)	0.7653 (7)	0.0232 (9)
H8	0.6223	0.3127	0.9385	0.028*
C9	0.64371 (13)	0.1181 (6)	0.6978 (7)	0.0300 (10)
H9A	0.6318	0.0076	0.7714	0.045*
H9B	0.6735	0.1319	0.7517	0.045*
H9C	0.6416	0.1028	0.5277	0.045*
C10	0.54098 (12)	0.4076 (7)	0.7644 (6)	0.0313 (9)
H10A	0.547	0.4429	0.9281	0.047*
H10B	0.512	0.3593	0.7441	0.047*
H10C	0.5439	0.5178	0.6646	0.047*
N1	0.57185 (10)	0.2572 (4)	0.6970 (5)	0.0246 (8)
H11	0.569	0.2411	0.5379	0.029*
H12	0.5643	0.1464	0.7648	0.029*
O1	0.61847 (10)	0.4596 (4)	0.3975 (5)	0.0288 (7)
H6	0.6147 (14)	0.555 (6)	0.334 (8)	0.035*
O2	0.55023 (8)	0.8906 (4)	0.8922 (4)	0.0275 (6)
O3	0.52720 (9)	0.7720 (4)	1.2722 (5)	0.0323 (7)
H13	0.5025	0.8084	1.2358	0.048*
O4	0.55403 (10)	1.0985 (4)	1.2305 (5)	0.0380 (8)
O5	0.60190 (9)	0.8243 (4)	1.2223 (5)	0.0365 (8)
S1	0.56039 (3)	0.90469 (14)	1.15108 (16)	0.0264 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.038 (3)	0.021 (2)	0.027 (2)	−0.004 (2)	0.0035 (19)	−0.0013 (18)
C2	0.034 (3)	0.023 (2)	0.025 (2)	−0.002 (2)	−0.003 (2)	−0.0041 (19)
C3	0.029 (2)	0.024 (2)	0.029 (2)	−0.0036 (18)	0.0016 (19)	0.0044 (18)
C4	0.032 (2)	0.021 (2)	0.022 (2)	−0.0002 (17)	0.0053 (18)	0.0011 (16)
C5	0.031 (2)	0.022 (2)	0.0194 (18)	−0.0052 (17)	0.0006 (17)	−0.0005 (17)
C6	0.029 (2)	0.0193 (19)	0.023 (2)	0.0000 (18)	0.0024 (18)	0.0041 (16)
C7	0.027 (2)	0.023 (2)	0.023 (2)	−0.0015 (18)	0.0007 (17)	−0.0011 (17)
C8	0.021 (2)	0.027 (2)	0.021 (2)	−0.0040 (18)	−0.0008 (17)	−0.0016 (18)
C9	0.029 (2)	0.024 (2)	0.037 (2)	0.0006 (19)	0.0008 (18)	0.0033 (19)
C10	0.030 (2)	0.029 (2)	0.036 (2)	0.004 (2)	0.0046 (17)	0.001 (2)
N1	0.030 (2)	0.0217 (17)	0.0218 (18)	−0.0017 (15)	−0.0004 (15)	0.0021 (15)
O1	0.0368 (17)	0.0261 (18)	0.0228 (14)	−0.0035 (13)	−0.0040 (12)	0.0053 (12)
O2	0.0335 (15)	0.0282 (14)	0.0211 (13)	−0.0047 (15)	0.0027 (11)	−0.0005 (15)
O3	0.0273 (17)	0.0339 (16)	0.0360 (17)	0.0002 (14)	0.0033 (13)	0.0136 (14)
O4	0.058 (2)	0.0223 (15)	0.0327 (17)	0.0022 (15)	−0.0088 (14)	−0.0038 (13)
O5	0.0279 (18)	0.0368 (18)	0.0439 (19)	0.0031 (13)	−0.0048 (14)	0.0104 (14)
S1	0.0300 (6)	0.0228 (5)	0.0262 (5)	−0.0021 (5)	−0.0016 (4)	0.0036 (5)

Geometric parameters (Å, º)

C1—C2	1.380 (6)	C8—H8	0.98
C1—C6	1.390 (5)	C9—H9A	0.96
C1—H1	1.00 (4)	C9—H9B	0.96
C2—C3	1.386 (6)	C9—H9C	0.96
C2—H2	0.90 (4)	C10—N1	1.485 (5)
C3—C4	1.389 (5)	C10—H10A	0.96
C3—H3	0.93	C10—H10B	0.96
C4—C5	1.386 (5)	C10—H10C	0.96
C4—H4	0.95 (4)	N1—H11	0.9
C5—C6	1.390 (5)	N1—H12	0.9
C5—H5	0.94 (4)	O1—H6	0.76 (4)
C6—C7	1.514 (6)	O2—S1	1.473 (2)
C7—O1	1.424 (4)	O3—S1	1.569 (3)
C7—C8	1.536 (5)	O3—H13	0.82
C7—H7	0.98	O4—S1	1.443 (3)
C8—N1	1.508 (5)	O5—S1	1.439 (3)
C8—C9	1.516 (5)
C2—C1—C6	120.6 (4)	C9—C8—H8	108.8
C2—C1—H1	119 (2)	C7—C8—H8	108.8
C6—C1—H1	120 (2)	C8—C9—H9A	109.5
C1—C2—C3	120.5 (4)	C8—C9—H9B	109.5
C1—C2—H2	119 (3)	H9A—C9—H9B	109.5
C3—C2—H2	121 (3)	C8—C9—H9C	109.5
C2—C3—C4	119.5 (4)	H9A—C9—H9C	109.5
C2—C3—H3	120.3	H9B—C9—H9C	109.5
C4—C3—H3	120.3	N1—C10—H10A	109.5
C5—C4—C3	119.7 (4)	N1—C10—H10B	109.5
C5—C4—H4	120 (2)	H10A—C10—H10B	109.5
C3—C4—H4	120 (2)	N1—C10—H10C	109.5
C4—C5—C6	121.0 (3)	H10A—C10—H10C	109.5
C4—C5—H5	120 (2)	H10B—C10—H10C	109.5
C6—C5—H5	119 (2)	C10—N1—C8	116.0 (3)
C1—C6—C5	118.6 (4)	C10—N1—H11	108.3
C1—C6—C7	120.5 (4)	C8—N1—H11	108.3
C5—C6—C7	120.7 (3)	C10—N1—H12	108.3
O1—C7—C6	113.3 (3)	C8—N1—H12	108.3
O1—C7—C8	106.0 (3)	H11—N1—H12	107.4
C6—C7—C8	110.4 (3)	C7—O1—H6	113 (3)
O1—C7—H7	109	S1—O3—H13	109.5
C6—C7—H7	109	O5—S1—O4	114.60 (17)
C8—C7—H7	109	O5—S1—O2	112.61 (16)
N1—C8—C9	106.9 (3)	O4—S1—O2	110.05 (17)
N1—C8—C7	108.4 (3)	O5—S1—O3	104.30 (16)
C9—C8—C7	114.9 (3)	O4—S1—O3	108.40 (19)
N1—C8—H8	108.8	O2—S1—O3	106.30 (16)
C6—C1—C2—C3	0.0 (6)	C5—C6—C7—O1	−25.6 (5)
C1—C2—C3—C4	1.1 (6)	C1—C6—C7—C8	−82.2 (4)
C2—C3—C4—C5	−0.7 (5)	C5—C6—C7—C8	93.0 (4)
C3—C4—C5—C6	−0.9 (5)	O1—C7—C8—N1	−50.5 (4)
C2—C1—C6—C5	−1.5 (6)	C6—C7—C8—N1	−173.4 (3)
C2—C1—C6—C7	173.8 (4)	O1—C7—C8—C9	69.0 (4)
C4—C5—C6—C1	2.0 (5)	C6—C7—C8—C9	−54.0 (4)
C4—C5—C6—C7	−173.3 (3)	C9—C8—N1—C10	175.6 (3)
C1—C6—C7—O1	159.2 (3)	C7—C8—N1—C10	−60.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O4^i	0.9	2.02	2.869 (4)	156
O1—H6···O5^ii	0.76 (4)	2.01 (4)	2.768 (4)	170 (5)
N1—H12···O2^iii	0.9	1.98	2.881 (4)	175
N1—H12···S1^iii	0.9	2.76	3.578 (3)	152
O3—H13···O2^iv	0.82	1.84	2.653 (4)	171
O3—H13···S1^iv	0.82	2.91	3.623 (3)	146

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

(EPHETART1) (1R, 2S)-(-)-ephedrine L-(+)-tartrate monohydrate

Crystal data

C14H23NO8	F(000) = 712
Mr = 333.33	Dx = 1.349 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1411 reflections
a = 6.6220 (2) Å	θ = 0–0°
b = 7.4620 (3) Å	µ = 0.11 mm^−1
c = 33.2160 (15) Å	T = 150 K
V = 1641.31 (11) Å^3	Plate, colourless
Z = 4	0.25 × 0.25 × 0.05 mm

Data collection

KappaCCD diffractometer	1789 independent reflections
Radiation source: Enraf Nonius FR590	1362 reflections with I > 2σ(I)
Graphite monochromator	θmax = 25.7°, θmin = 4.1°
CCD rotation images, thick slices scans	h = 0→7
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	k = 0→9
Tmin = 0.962, Tmax = 1.02	l = 0→40
1789 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0312P)^2 + 0.535P] where P = (Fo^2 + 2Fc^2)/3
1789 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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
C1	0.9589 (7)	0.7626 (5)	0.25786 (10)	0.0282 (9)
H1	1.087 (6)	0.707 (5)	0.2610 (10)	0.034*
C2	0.8679 (7)	0.7652 (5)	0.21982 (11)	0.0327 (10)
H2	0.935 (6)	0.712 (5)	0.2000 (10)	0.039*
C3	0.6841 (7)	0.8478 (5)	0.21453 (11)	0.0329 (10)
H3	0.629 (6)	0.849 (5)	0.1879 (11)	0.039*
C4	0.5886 (6)	0.9293 (5)	0.24668 (10)	0.0336 (10)
H4	0.445 (6)	0.995 (5)	0.2429 (10)	0.04*
C5	0.6794 (6)	0.9271 (5)	0.28445 (10)	0.0268 (9)
H5	0.620 (6)	0.975 (5)	0.3046 (10)	0.032*
C6	0.8636 (5)	0.8442 (4)	0.29030 (9)	0.0215 (8)
C7	0.9608 (6)	0.8340 (5)	0.33154 (9)	0.0208 (8)
H7	1.111 (6)	0.860 (4)	0.3284 (9)	0.025*
C8	0.9254 (6)	0.6497 (5)	0.35107 (9)	0.0216 (8)
H8	1.018 (6)	0.560 (5)	0.3369 (9)	0.026*
C9	0.7066 (6)	0.5896 (6)	0.35069 (12)	0.0300 (9)
H9A	0.657 (6)	0.577 (5)	0.3221 (11)	0.036*
H9B	0.699 (6)	0.483 (5)	0.3652 (11)	0.036*
H9C	0.622 (6)	0.676 (5)	0.3643 (10)	0.036*
C10	1.2209 (6)	0.6605 (6)	0.39925 (12)	0.0279 (9)
H12A	1.280 (6)	0.564 (5)	0.3849 (10)	0.033*
H12B	1.273 (6)	0.772 (5)	0.3893 (10)	0.033*
H12C	1.247 (5)	0.650 (4)	0.4302 (11)	0.033*
C11	0.6022 (5)	0.8044 (4)	0.47101 (10)	0.0196 (7)
C12	0.5932 (5)	0.9981 (4)	0.45559 (9)	0.0174 (7)
H13	0.482 (6)	1.063 (4)	0.4693 (9)	0.021*
C13	0.7946 (5)	1.0856 (4)	0.46695 (10)	0.0182 (8)
H15	0.804 (5)	1.080 (4)	0.4962 (10)	0.022*
C14	0.7937 (5)	1.2806 (4)	0.45358 (9)	0.0193 (8)
O1	0.8810 (4)	0.9684 (3)	0.35767 (6)	0.0232 (6)
H6	0.9729	1.0328	0.3657	0.035*
O2	0.6298 (3)	0.6817 (3)	0.44457 (6)	0.0220 (5)
O3	0.5862 (4)	0.7800 (3)	0.50762 (6)	0.0262 (6)
O4	0.9564 (3)	0.9938 (3)	0.44803 (6)	0.0204 (5)
H16	1.005	0.921	0.4638	0.031*
O5	0.5563 (3)	1.0124 (3)	0.41350 (6)	0.0213 (5)
H14	0.6577	0.9821	0.4011	0.032*
O6	0.9189 (4)	1.3369 (3)	0.42906 (7)	0.0263 (6)
O7	0.6541 (4)	1.3744 (3)	0.46977 (7)	0.0278 (6)
H17	0.6523	1.4743	0.4595	0.042*
O8	0.7976 (4)	0.6740 (3)	0.11874 (7)	0.0268 (6)
H18	0.694 (6)	0.623 (5)	0.1098 (11)	0.032*
H19	0.869 (6)	0.709 (5)	0.0974 (11)	0.032*
N1	0.9988 (4)	0.6565 (4)	0.39388 (7)	0.0190 (6)
H10	0.9464	0.7546	0.4057	0.023*
H11	0.95	0.5603	0.407	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.035 (2)	0.025 (2)	0.0248 (19)	0.0057 (18)	0.0021 (19)	0.0018 (16)
C2	0.054 (3)	0.026 (2)	0.0177 (18)	0.004 (2)	0.0013 (19)	−0.0023 (16)
C3	0.048 (3)	0.027 (2)	0.0237 (19)	−0.002 (2)	−0.0091 (19)	0.0001 (18)
C4	0.038 (3)	0.035 (2)	0.0283 (19)	0.004 (2)	−0.006 (2)	0.0051 (18)
C5	0.029 (2)	0.031 (2)	0.0204 (18)	0.0038 (18)	0.0033 (17)	−0.0014 (17)
C6	0.029 (2)	0.0197 (17)	0.0162 (16)	−0.0019 (17)	0.0029 (15)	0.0028 (14)
C7	0.020 (2)	0.0223 (18)	0.0198 (17)	−0.0013 (17)	0.0028 (15)	−0.0013 (15)
C8	0.029 (2)	0.0207 (18)	0.0147 (17)	−0.0014 (17)	0.0024 (15)	−0.0017 (15)
C9	0.030 (2)	0.036 (2)	0.024 (2)	−0.0112 (19)	−0.0039 (18)	0.0059 (19)
C10	0.022 (2)	0.031 (2)	0.031 (2)	−0.0032 (19)	0.0014 (17)	0.0058 (19)
C11	0.0133 (18)	0.0186 (17)	0.0268 (18)	−0.0022 (15)	−0.0003 (16)	0.0026 (15)
C12	0.021 (2)	0.0138 (17)	0.0172 (16)	0.0037 (15)	0.0032 (15)	−0.0008 (14)
C13	0.0215 (19)	0.0189 (18)	0.0142 (16)	0.0030 (15)	0.0008 (15)	−0.0004 (15)
C14	0.0214 (19)	0.0209 (18)	0.0156 (16)	−0.0016 (16)	−0.0001 (17)	−0.0028 (15)
O1	0.0293 (14)	0.0203 (12)	0.0199 (11)	−0.0015 (11)	0.0004 (11)	−0.0011 (10)
O2	0.0254 (13)	0.0157 (11)	0.0250 (12)	0.0015 (11)	0.0002 (11)	−0.0024 (10)
O3	0.0393 (16)	0.0173 (12)	0.0219 (13)	−0.0047 (11)	0.0054 (12)	0.0032 (10)
O4	0.0213 (14)	0.0181 (12)	0.0220 (11)	0.0040 (10)	−0.0004 (11)	0.0026 (10)
O5	0.0197 (13)	0.0252 (13)	0.0190 (11)	0.0023 (11)	0.0000 (10)	0.0000 (10)
O6	0.0292 (15)	0.0182 (12)	0.0316 (13)	0.0014 (12)	0.0089 (12)	0.0048 (11)
O7	0.0336 (16)	0.0122 (12)	0.0374 (14)	0.0028 (11)	0.0135 (13)	0.0039 (11)
O8	0.0237 (14)	0.0292 (14)	0.0275 (14)	−0.0024 (13)	0.0024 (12)	−0.0009 (12)
N1	0.0208 (16)	0.0171 (14)	0.0190 (14)	−0.0014 (13)	0.0011 (12)	0.0008 (12)

Geometric parameters (Å, º)

C1—C6	1.389 (5)	C10—H12A	0.95 (4)
C1—C2	1.400 (5)	C10—H12B	0.96 (4)
C1—H1	0.95 (4)	C10—H12C	1.05 (3)
C2—C3	1.376 (6)	C11—O3	1.234 (4)
C2—H2	0.89 (4)	C11—O2	1.281 (4)
C3—C4	1.382 (5)	C11—C12	1.535 (4)
C3—H3	0.96 (3)	C12—O5	1.423 (4)
C4—C5	1.391 (5)	C12—C13	1.532 (5)
C4—H4	1.08 (4)	C12—H13	0.99 (4)
C5—C6	1.381 (5)	C13—O4	1.419 (4)
C5—H5	0.86 (4)	C13—C14	1.521 (5)
C6—C7	1.516 (4)	C13—H15	0.97 (3)
C7—O1	1.428 (4)	C14—O6	1.236 (4)
C7—C8	1.538 (5)	C14—O7	1.278 (4)
C7—H7	1.02 (4)	O1—H6	0.82
C8—N1	1.504 (4)	O4—H16	0.82
C8—C9	1.517 (5)	O5—H14	0.82
C8—H8	1.02 (4)	O7—H17	0.82
C9—H9A	1.01 (4)	O8—H18	0.84 (4)
C9—H9B	0.93 (4)	O8—H19	0.89 (4)
C9—H9C	0.96 (4)	N1—H10	0.9
C10—N1	1.481 (5)	N1—H11	0.9
C6—C1—C2	119.9 (4)	N1—C10—H12A	109 (2)
C6—C1—H1	121 (2)	N1—C10—H12B	110 (2)
C2—C1—H1	119 (2)	H12A—C10—H12B	110 (3)
C3—C2—C1	120.1 (4)	N1—C10—H12C	106.3 (19)
C3—C2—H2	123 (2)	H12A—C10—H12C	112 (3)
C1—C2—H2	117 (2)	H12B—C10—H12C	110 (3)
C2—C3—C4	120.2 (4)	O3—C11—O2	125.6 (3)
C2—C3—H3	117 (2)	O3—C11—C12	117.7 (3)
C4—C3—H3	122 (2)	O2—C11—C12	116.7 (3)
C3—C4—C5	119.6 (4)	O5—C12—C13	111.1 (3)
C3—C4—H4	120.9 (18)	O5—C12—C11	113.9 (3)
C5—C4—H4	119.5 (19)	C13—C12—C11	106.6 (3)
C6—C5—C4	120.9 (4)	O5—C12—H13	106.8 (18)
C6—C5—H5	119 (2)	C13—C12—H13	108.9 (19)
C4—C5—H5	120 (2)	C11—C12—H13	109.5 (18)
C5—C6—C1	119.2 (3)	O4—C13—C14	109.6 (3)
C5—C6—C7	121.6 (3)	O4—C13—C12	110.0 (2)
C1—C6—C7	119.1 (3)	C14—C13—C12	109.4 (3)
O1—C7—C6	110.9 (3)	O4—C13—H15	111.9 (19)
O1—C7—C8	108.4 (3)	C14—C13—H15	109.2 (18)
C6—C7—C8	111.2 (3)	C12—C13—H15	106.6 (19)
O1—C7—H7	107.0 (19)	O6—C14—O7	125.2 (3)
C6—C7—H7	108.3 (18)	O6—C14—C13	121.0 (3)
C8—C7—H7	111.0 (19)	O7—C14—C13	113.8 (3)
N1—C8—C9	109.1 (3)	C7—O1—H6	109.5
N1—C8—C7	108.6 (3)	C13—O4—H16	109.5
C9—C8—C7	114.0 (3)	C12—O5—H14	109.5
N1—C8—H8	105.2 (18)	C14—O7—H17	109.5
C9—C8—H8	112 (2)	H18—O8—H19	106 (3)
C7—C8—H8	107.6 (18)	C10—N1—C8	115.8 (3)
C8—C9—H9A	110 (2)	C10—N1—H10	108.3
C8—C9—H9B	108 (2)	C8—N1—H10	108.3
H9A—C9—H9B	113 (3)	C10—N1—H11	108.3
C8—C9—H9C	111 (2)	C8—N1—H11	108.3
H9A—C9—H9C	108 (3)	H10—N1—H11	107.4
H9B—C9—H9C	107 (3)
C6—C1—C2—C3	−0.2 (6)	C6—C7—C8—C9	−50.2 (4)
C1—C2—C3—C4	0.3 (6)	O3—C11—C12—O5	−163.4 (3)
C2—C3—C4—C5	−0.1 (6)	O2—C11—C12—O5	17.9 (4)
C3—C4—C5—C6	−0.1 (6)	O3—C11—C12—C13	73.7 (4)
C4—C5—C6—C1	0.2 (5)	O2—C11—C12—C13	−104.9 (3)
C4—C5—C6—C7	−177.5 (3)	O5—C12—C13—O4	−63.4 (3)
C2—C1—C6—C5	0.0 (5)	C11—C12—C13—O4	61.2 (3)
C2—C1—C6—C7	177.8 (3)	O5—C12—C13—C14	57.1 (3)
C5—C6—C7—O1	−20.8 (4)	C11—C12—C13—C14	−178.4 (3)
C1—C6—C7—O1	161.5 (3)	O4—C13—C14—O6	1.4 (4)
C5—C6—C7—C8	99.8 (4)	C12—C13—C14—O6	−119.3 (3)
C1—C6—C7—C8	−77.9 (4)	O4—C13—C14—O7	−178.9 (3)
O1—C7—C8—N1	−49.9 (4)	C12—C13—C14—O7	60.4 (3)
C6—C7—C8—N1	−172.0 (3)	C9—C8—N1—C10	162.8 (3)
O1—C7—C8—C9	71.9 (4)	C7—C8—N1—C10	−72.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H16···O3^i	0.82	1.86	2.661 (3)	167
O1—H6···O8^ii	0.82	1.92	2.738 (3)	175
N1—H11···O6^iii	0.9	1.83	2.709 (3)	164
O8—H18···O5^iv	0.84 (4)	2.01 (4)	2.845 (3)	177 (4)
O8—H19···O6^v	0.89 (4)	1.91 (4)	2.743 (3)	154 (3)
O8—H19···O4^v	0.89 (4)	2.49 (3)	3.063 (3)	122 (3)
O7—H17···O2^vi	0.82	1.63	2.446 (3)	172

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

(EPHETART3) (1R, 2S)-(-)-ephedrine L-(+)-tartrate trihydrate

Crystal data

C24H42N2O11	Z = 1
Mr = 534.6	F(000) = 288
Triclinic, P1	Dx = 1.279 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9373 (2) Å	Cell parameters from 25777 reflections
b = 7.0594 (2) Å	θ = 1.0–25.0°
c = 18.3791 (8) Å	µ = 0.10 mm^−1
α = 80.254 (1)°	T = 150 K
β = 88.527 (2)°	Plate, colourless
γ = 66.247 (2)°	0.25 × 0.25 × 0.05 mm
V = 694.14 (4) Å^3

Data collection

KappaCCD diffractometer	2412 independent reflections
Radiation source: Enraf Nonius FR590	2078 reflections with I > 2σ(I)
Graphite monochromator	θmax = 25.0°, θmin = 3.2°
CCD rotation images, thick slices scans	h = −7→7
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	k = −8→8
Tmin = 0.879, Tmax = 1.158	l = −21→19
6838 measured reflections

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)] = 0.098	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.295	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.31	(Δ/σ)max = 0.007
2412 reflections	Δρmax = 0.59 e Å^−3
349 parameters	Δρmin = −0.43 e Å^−3
3 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.44 (9)

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
C01	0.871 (2)	0.1721 (17)	1.1790 (6)	0.057 (3)
H01	0.7494	0.1787	1.1464	0.069*
C02	0.925 (2)	0.033 (2)	1.2468 (7)	0.070 (3)
H02	0.836	−0.0493	1.2595	0.084*
C03	1.109 (2)	0.0169 (18)	1.2943 (6)	0.060 (3)
H03	1.1454	−0.0772	1.3388	0.072*
C04	1.240 (2)	0.1419 (15)	1.2760 (5)	0.051 (2)
H04	1.3636	0.1324	1.3081	0.062*
C05	1.1823 (17)	0.2839 (14)	1.2077 (5)	0.047 (2)
H05	1.2707	0.3665	1.1949	0.056*
C06	0.9975 (15)	0.3001 (12)	1.1606 (4)	0.0383 (18)
C07	0.9281 (15)	0.4561 (13)	1.0880 (4)	0.0370 (17)
H07	0.9352	0.3798	1.0476	0.044*
C08	0.6637 (16)	0.6258 (12)	1.0890 (5)	0.0386 (19)
C09	0.621 (2)	0.7431 (18)	1.1535 (6)	0.067 (3)
H09A	0.7453	0.7973	1.1555	0.1*
H09B	0.6306	0.6489	1.1987	0.1*
H09C	0.4615	0.8573	1.1471	0.1*
C10	0.3560 (19)	0.8877 (17)	0.9919 (6)	0.053 (2)
H12A	0.3068	0.794	0.9708	0.079*
H12B	0.3367	1.0078	0.955	0.079*
H12C	0.2552	0.9329	1.0325	0.079*
C11	1.0959 (17)	0.5183 (13)	0.8929 (5)	0.0417 (19)
C12	1.1825 (16)	0.4567 (13)	0.8185 (5)	0.0421 (19)
H13	1.2718	0.3035	0.8268	0.051*
C13	1.3653 (14)	0.5513 (11)	0.7876 (5)	0.0346 (17)
H14	1.5011	0.507	0.8245	0.042*
C14	1.4718 (13)	0.4785 (11)	0.7163 (5)	0.0336 (17)
C21	0.7053 (17)	0.7605 (13)	0.4616 (5)	0.044 (2)
H21	0.5487	0.8442	0.4746	0.053*
C22	0.731 (2)	0.6825 (16)	0.3962 (5)	0.053 (2)
H22	0.5937	0.7143	0.3658	0.063*
C23	0.963 (2)	0.5571 (14)	0.3762 (5)	0.052 (2)
H23	0.9808	0.503	0.3326	0.062*
C24	1.167 (2)	0.5125 (15)	0.4204 (6)	0.054 (2)
H24	1.3232	0.4298	0.4065	0.064*
C25	1.1406 (16)	0.5920 (14)	0.4868 (5)	0.0420 (19)
H25	1.2787	0.5617	0.5168	0.05*
C26	0.9045 (15)	0.7175 (12)	0.5077 (5)	0.0366 (18)
C27	0.8824 (14)	0.8062 (12)	0.5784 (5)	0.0372 (18)
H27	0.986	0.6946	0.6177	0.045*
C28	0.9715 (15)	0.9843 (11)	0.5667 (4)	0.0324 (16)
C29	0.809 (2)	1.1765 (14)	0.5132 (5)	0.052 (2)
H29A	0.644	1.2267	0.5295	0.077*
H29B	0.811	1.1407	0.465	0.077*
H29C	0.8704	1.2842	0.5109	0.077*
C30	1.0894 (16)	1.1982 (12)	0.6451 (5)	0.0413 (19)
H32A	1.2458	1.1539	0.6225	0.062*
H32B	1.112	1.2073	0.6957	0.062*
H32C	0.9808	1.3335	0.619	0.062*
O01	1.0899 (12)	0.5557 (11)	1.0747 (4)	0.0481 (16)
H06	1.2322	0.4681	1.0828	0.072*
O02	0.8714 (11)	0.6330 (10)	0.8980 (3)	0.0460 (15)
O03	1.2568 (12)	0.4514 (11)	0.9439 (4)	0.0512 (17)
O04	0.9895 (11)	0.5091 (11)	0.7662 (4)	0.0482 (16)
H15	0.863	0.5201	0.7875	0.072*
O05	1.2373 (10)	0.7757 (8)	0.7781 (4)	0.0422 (14)
H16	1.1227	0.8062	0.8059	0.063*
O06	1.4444 (12)	0.6083 (10)	0.6597 (3)	0.0474 (15)
O07	1.5890 (12)	0.2805 (9)	0.7206 (4)	0.0489 (16)
O08	1.5864 (13)	0.9141 (11)	0.7831 (4)	0.0523 (16)
H17A	1.7169	0.8062	0.7967	0.063*
H17B	1.4963	0.8789	0.7573	0.063*
O09	0.7162 (12)	0.1428 (11)	0.9908 (4)	0.0505 (16)
H18A	0.8368	0.1702	0.9732	0.061*
H18B	0.5857	0.2524	0.9787	0.061*
O10	0.9462 (12)	0.1046 (10)	0.8566 (4)	0.0504 (16)
H19A	1.0832	0.0315	0.8394	0.06*
H19B	0.8393	0.1534	0.8199	0.06*
O21	0.6383 (11)	0.8885 (10)	0.6011 (4)	0.0442 (14)
H26	0.5443	0.9534	0.565	0.066*
N01	0.6160 (13)	0.7781 (11)	1.0185 (4)	0.0397 (16)
H11	0.6732	0.8749	1.0244	0.048*
H10A	0.7028	0.7089	0.9832	0.048*
N21	0.9799 (12)	1.0424 (10)	0.6419 (4)	0.0355 (15)
H30	0.8253	1.0946	0.6574	0.043*
H31	1.067	0.9243	0.6738	0.043*
H08	0.551 (19)	0.549 (19)	1.086 (6)	0.043*
H28	1.12 (2)	0.966 (18)	0.548 (6)	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C01	0.066 (6)	0.051 (6)	0.050 (5)	−0.025 (5)	−0.007 (4)	0.011 (4)
C02	0.076 (7)	0.054 (7)	0.071 (7)	−0.028 (6)	−0.009 (6)	0.021 (6)
C03	0.072 (7)	0.049 (6)	0.046 (5)	−0.016 (5)	−0.002 (5)	0.002 (4)
C04	0.069 (6)	0.034 (5)	0.038 (4)	−0.005 (4)	−0.008 (4)	−0.009 (4)
C05	0.054 (5)	0.031 (4)	0.049 (5)	−0.009 (4)	0.002 (4)	−0.011 (4)
C06	0.049 (4)	0.022 (4)	0.037 (4)	−0.006 (3)	0.007 (3)	−0.007 (3)
C07	0.047 (4)	0.030 (4)	0.031 (4)	−0.010 (3)	0.004 (3)	−0.009 (3)
C08	0.053 (5)	0.016 (4)	0.039 (4)	−0.006 (3)	0.005 (3)	−0.006 (3)
C09	0.086 (8)	0.041 (6)	0.049 (6)	0.004 (5)	0.009 (5)	−0.021 (5)
C10	0.051 (5)	0.043 (5)	0.056 (6)	−0.016 (4)	−0.007 (4)	0.006 (4)
C11	0.052 (5)	0.028 (4)	0.042 (5)	−0.015 (4)	0.008 (4)	−0.003 (3)
C12	0.044 (4)	0.026 (4)	0.057 (5)	−0.014 (3)	0.013 (4)	−0.012 (4)
C13	0.038 (4)	0.013 (3)	0.048 (5)	−0.007 (3)	−0.004 (3)	−0.001 (3)
C14	0.036 (4)	0.024 (4)	0.044 (4)	−0.014 (3)	0.001 (3)	−0.007 (3)
C21	0.048 (5)	0.028 (4)	0.045 (5)	−0.007 (4)	−0.007 (4)	0.005 (4)
C22	0.078 (7)	0.050 (6)	0.027 (4)	−0.024 (5)	−0.012 (4)	0.001 (4)
C23	0.077 (6)	0.029 (4)	0.045 (5)	−0.016 (4)	0.005 (4)	−0.012 (4)
C24	0.065 (6)	0.034 (5)	0.053 (6)	−0.009 (4)	0.016 (5)	−0.015 (4)
C25	0.043 (4)	0.028 (4)	0.044 (4)	−0.005 (3)	0.001 (3)	−0.003 (3)
C26	0.044 (4)	0.022 (4)	0.046 (5)	−0.015 (3)	0.006 (3)	−0.009 (3)
C27	0.039 (4)	0.023 (4)	0.043 (4)	−0.006 (3)	0.004 (3)	−0.005 (3)
C28	0.040 (4)	0.022 (4)	0.034 (4)	−0.011 (3)	0.006 (3)	−0.005 (3)
C29	0.078 (6)	0.030 (4)	0.041 (5)	−0.019 (4)	−0.006 (4)	0.003 (4)
C30	0.055 (5)	0.020 (4)	0.044 (4)	−0.012 (3)	0.004 (4)	−0.003 (3)
O01	0.045 (3)	0.060 (4)	0.041 (3)	−0.025 (3)	0.002 (2)	−0.003 (3)
O02	0.048 (3)	0.037 (3)	0.042 (3)	−0.005 (3)	0.009 (3)	−0.007 (3)
O03	0.055 (4)	0.045 (4)	0.036 (3)	−0.005 (3)	0.010 (3)	−0.005 (3)
O04	0.047 (3)	0.058 (4)	0.049 (4)	−0.026 (3)	0.014 (3)	−0.026 (3)
O05	0.043 (3)	0.017 (3)	0.061 (4)	−0.006 (2)	0.004 (3)	−0.008 (2)
O06	0.054 (3)	0.046 (4)	0.041 (3)	−0.022 (3)	0.002 (3)	0.000 (3)
O07	0.059 (4)	0.024 (3)	0.060 (4)	−0.012 (3)	0.022 (3)	−0.013 (3)
O08	0.060 (4)	0.040 (3)	0.058 (4)	−0.023 (3)	−0.011 (3)	−0.003 (3)
O09	0.050 (3)	0.038 (3)	0.059 (4)	−0.012 (3)	0.001 (3)	−0.009 (3)
O10	0.056 (3)	0.034 (3)	0.051 (4)	−0.007 (3)	−0.001 (3)	−0.006 (3)
O21	0.041 (3)	0.034 (3)	0.055 (4)	−0.013 (2)	0.007 (3)	−0.007 (3)
N01	0.047 (4)	0.026 (3)	0.041 (4)	−0.008 (3)	0.005 (3)	−0.009 (3)
N21	0.042 (3)	0.029 (3)	0.032 (3)	−0.011 (3)	0.004 (3)	−0.005 (3)

Geometric parameters (Å, º)

C01—C06	1.389 (14)	C21—H21	0.93
C01—C02	1.405 (16)	C22—C23	1.384 (16)
C01—H01	0.93	C22—H22	0.93
C02—C03	1.371 (18)	C23—C24	1.373 (16)
C02—H02	0.93	C23—H23	0.93
C03—C04	1.391 (17)	C24—C25	1.407 (14)
C03—H03	0.93	C24—H24	0.93
C04—C05	1.420 (14)	C25—C26	1.410 (12)
C04—H04	0.93	C25—H25	0.93
C05—C06	1.372 (13)	C26—C27	1.514 (11)
C05—H05	0.93	C27—O21	1.409 (10)
C06—C07	1.525 (11)	C27—C28	1.531 (11)
C07—O01	1.397 (11)	C27—H27	0.98
C07—C08	1.546 (11)	C28—C29	1.510 (12)
C07—H07	0.98	C28—N21	1.514 (10)
C08—N01	1.489 (11)	C28—H28	0.93 (12)
C08—C09	1.519 (12)	C29—H29A	0.96
C08—H08	1.03 (12)	C29—H29B	0.96
C09—H09A	0.96	C29—H29C	0.96
C09—H09B	0.96	C30—N21	1.496 (11)
C09—H09C	0.96	C30—H32A	0.96
C10—N01	1.472 (12)	C30—H32B	0.96
C10—H12A	0.96	C30—H32C	0.96
C10—H12B	0.96	O01—H06	0.82
C10—H12C	0.96	O04—H15	0.82
C11—O03	1.244 (12)	O05—H16	0.82
C11—O02	1.261 (11)	O08—H17A	0.8445
C11—C12	1.519 (12)	O08—H17B	0.8564
C12—O04	1.404 (12)	O09—H18A	0.8562
C12—C13	1.539 (11)	O09—H18B	0.8464
C12—H13	0.98	O10—H19A	0.8551
C13—O05	1.435 (9)	O10—H19B	0.861
C13—C14	1.518 (11)	O21—H26	0.82
C13—H14	0.98	N01—H11	0.9
C14—O06	1.231 (11)	N01—H10A	0.9
C14—O07	1.275 (10)	N21—H30	0.9
C21—C26	1.373 (13)	N21—H31	0.9
C21—C22	1.384 (14)
C06—C01—C02	120.1 (10)	C26—C21—H21	119.1
C06—C01—H01	119.9	C22—C21—H21	119.1
C02—C01—H01	119.9	C23—C22—C21	119.8 (9)
C03—C02—C01	120.5 (11)	C23—C22—H22	120.1
C03—C02—H02	119.8	C21—C22—H22	120.1
C01—C02—H02	119.8	C24—C23—C22	120.2 (9)
C02—C03—C04	119.9 (10)	C24—C23—H23	119.9
C02—C03—H03	120.1	C22—C23—H23	119.9
C04—C03—H03	120.1	C23—C24—C25	119.9 (8)
C03—C04—C05	119.4 (9)	C23—C24—H24	120.1
C03—C04—H04	120.3	C25—C24—H24	120.1
C05—C04—H04	120.3	C24—C25—C26	120.0 (8)
C06—C05—C04	120.5 (9)	C24—C25—H25	120
C06—C05—H05	119.8	C26—C25—H25	120
C04—C05—H05	119.8	C21—C26—C25	118.3 (8)
C05—C06—C01	119.6 (8)	C21—C26—C27	122.9 (7)
C05—C06—C07	121.3 (8)	C25—C26—C27	118.7 (8)
C01—C06—C07	119.1 (8)	O21—C27—C26	112.7 (7)
O01—C07—C06	111.4 (7)	O21—C27—C28	107.6 (6)
O01—C07—C08	108.6 (7)	C26—C27—C28	109.6 (6)
C06—C07—C08	110.7 (6)	O21—C27—H27	108.9
O01—C07—H07	108.7	C26—C27—H27	108.9
C06—C07—H07	108.7	C28—C27—H27	108.9
C08—C07—H07	108.7	C29—C28—N21	109.7 (6)
N01—C08—C09	109.2 (7)	C29—C28—C27	114.1 (7)
N01—C08—C07	107.3 (6)	N21—C28—C27	106.5 (6)
C09—C08—C07	114.1 (8)	C29—C28—H28	99 (7)
N01—C08—H08	106 (6)	N21—C28—H28	105 (7)
C09—C08—H08	115 (6)	C27—C28—H28	121 (7)
C07—C08—H08	105 (6)	C28—C29—H29A	109.5
C08—C09—H09A	109.5	C28—C29—H29B	109.5
C08—C09—H09B	109.5	H29A—C29—H29B	109.5
H09A—C09—H09B	109.5	C28—C29—H29C	109.5
C08—C09—H09C	109.5	H29A—C29—H29C	109.5
H09A—C09—H09C	109.5	H29B—C29—H29C	109.5
H09B—C09—H09C	109.5	N21—C30—H32A	109.5
N01—C10—H12A	109.5	N21—C30—H32B	109.5
N01—C10—H12B	109.5	H32A—C30—H32B	109.5
H12A—C10—H12B	109.5	N21—C30—H32C	109.5
N01—C10—H12C	109.5	H32A—C30—H32C	109.5
H12A—C10—H12C	109.5	H32B—C30—H32C	109.5
H12B—C10—H12C	109.5	C07—O01—H06	109.5
O03—C11—O02	125.6 (8)	C12—O04—H15	109.5
O03—C11—C12	116.0 (8)	C13—O05—H16	109.5
O02—C11—C12	118.4 (8)	H17A—O08—H17B	107.6
O04—C12—C11	113.6 (7)	H18A—O09—H18B	107.5
O04—C12—C13	110.3 (7)	H19A—O10—H19B	106.2
C11—C12—C13	110.9 (7)	C27—O21—H26	109.5
O04—C12—H13	107.2	C10—N01—C08	115.4 (7)
C11—C12—H13	107.2	C10—N01—H11	108.4
C13—C12—H13	107.2	C08—N01—H11	108.4
O05—C13—C14	112.1 (6)	C10—N01—H10A	108.4
O05—C13—C12	107.2 (6)	C08—N01—H10A	108.4
C14—C13—C12	112.3 (6)	H11—N01—H10A	107.5
O05—C13—H14	108.4	C30—N21—C28	115.6 (6)
C14—C13—H14	108.4	C30—N21—H30	108.4
C12—C13—H14	108.4	C28—N21—H30	108.4
O06—C14—O07	124.5 (8)	C30—N21—H31	108.4
O06—C14—C13	119.9 (6)	C28—N21—H31	108.4
O07—C14—C13	115.6 (7)	H30—N21—H31	107.4
C26—C21—C22	121.8 (9)
C06—C01—C02—C03	−2 (2)	O05—C13—C14—O06	0.6 (10)
C01—C02—C03—C04	1.0 (19)	C12—C13—C14—O06	121.5 (8)
C02—C03—C04—C05	−0.4 (16)	O05—C13—C14—O07	179.8 (6)
C03—C04—C05—C06	0.8 (13)	C12—C13—C14—O07	−59.4 (9)
C04—C05—C06—C01	−1.8 (12)	C26—C21—C22—C23	0.2 (14)
C04—C05—C06—C07	178.3 (8)	C21—C22—C23—C24	−1.0 (15)
C02—C01—C06—C05	2.4 (15)	C22—C23—C24—C25	0.9 (15)
C02—C01—C06—C07	−177.6 (10)	C23—C24—C25—C26	−0.1 (14)
C05—C06—C07—O01	6.1 (10)	C22—C21—C26—C25	0.6 (12)
C01—C06—C07—O01	−173.8 (8)	C22—C21—C26—C27	178.0 (9)
C05—C06—C07—C08	−114.8 (8)	C24—C25—C26—C21	−0.7 (13)
C01—C06—C07—C08	65.2 (10)	C24—C25—C26—C27	−178.2 (8)
O01—C07—C08—N01	54.1 (8)	C21—C26—C27—O21	15.6 (11)
C06—C07—C08—N01	176.7 (7)	C25—C26—C27—O21	−167.0 (7)
O01—C07—C08—C09	−67.1 (10)	C21—C26—C27—C28	−104.2 (8)
C06—C07—C08—C09	55.5 (10)	C25—C26—C27—C28	73.1 (9)
O03—C11—C12—O04	171.0 (8)	O21—C27—C28—C29	−55.7 (9)
O02—C11—C12—O04	−9.8 (11)	C26—C27—C28—C29	67.1 (9)
O03—C11—C12—C13	−64.0 (10)	O21—C27—C28—N21	65.4 (8)
O02—C11—C12—C13	115.2 (8)	C26—C27—C28—N21	−171.8 (6)
O04—C12—C13—O05	65.7 (8)	C09—C08—N01—C10	−83.5 (10)
C11—C12—C13—O05	−61.1 (9)	C07—C08—N01—C10	152.4 (8)
O04—C12—C13—C14	−57.9 (8)	C29—C28—N21—C30	−62.7 (9)
C11—C12—C13—C14	175.3 (7)	C27—C28—N21—C30	173.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O05—H16···O10^i	0.82	2.29	2.869 (9)	128
N01—H11···O09^i	0.9	2	2.832 (10)	153
O08—H17A···O02^ii	0.84	2.05	2.705 (9)	134
O08—H17A···O04^ii	0.84	2.22	2.958 (10)	145
O09—H18B···O03^iii	0.85	1.94	2.762 (9)	165
O10—H19B···O07^iii	0.86	2.2	3.063 (10)	176
O10—H19A···O05^iv	0.86	2.16	2.869 (9)	140
N21—H30···O07^v	0.9	2	2.795 (9)	147

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) x, y−1, z; (v) x−1, y+1, z.

(EPHETOSY) (1R, 2S)-(-)-ephedrine P-tosylate

Crystal data

C17H23NO7S	F(000) = 720
Mr = 337.42	Dx = 1.294 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 19550 reflections
a = 5.7491 (2) Å	θ = 1.0–27.5°
b = 7.1665 (2) Å	µ = 0.21 mm^−1
c = 42.0343 (9) Å	T = 150 K
V = 1731.85 (9) Å^3	Plate, white
Z = 4	0.35 × 0.35 × 0.05 mm

Data collection

KappaCCD diffractometer	3446 independent reflections
Radiation source: Enraf Nonius FR590	2839 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −7→6
Tmin = 0.976, Tmax = 1.022	k = −9→9
6102 measured reflections	l = −39→54

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0389P)^2 + 0.3943P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3446 reflections	Δρmax = 0.24 e Å^−3
263 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (9)

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
C1	−0.0136 (5)	0.8334 (3)	0.30748 (7)	0.0388 (6)
H1	0.115 (5)	0.827 (4)	0.3222 (7)	0.047*
C2	0.0202 (5)	0.9236 (4)	0.27872 (8)	0.0518 (8)
H2	0.169 (5)	0.992 (4)	0.2735 (7)	0.062*
C3	−0.1510 (6)	0.9211 (4)	0.25576 (8)	0.0591 (9)
H3	−0.121 (5)	0.975 (5)	0.2342 (8)	0.071*
C4	−0.3549 (5)	0.8292 (5)	0.26177 (8)	0.0562 (8)
H4	−0.475 (6)	0.819 (4)	0.2464 (8)	0.067*
C5	−0.3920 (5)	0.7377 (4)	0.29042 (7)	0.0442 (7)
H5	−0.548 (5)	0.679 (4)	0.2963 (7)	0.053*
C6	−0.2218 (4)	0.7413 (3)	0.31369 (6)	0.0320 (5)
C7	−0.2538 (4)	0.6446 (3)	0.34531 (6)	0.0304 (5)
H7	−0.177 (4)	0.711 (3)	0.3607 (6)	0.036*
C8	−0.1373 (4)	0.4527 (4)	0.34526 (6)	0.0333 (5)
H8	0.041 (4)	0.475 (4)	0.3419 (6)	0.04*
C9	−0.2427 (6)	0.3176 (4)	0.32176 (7)	0.0500 (8)
H9A	−0.217 (5)	0.350 (4)	0.3018 (8)	0.06*
H9B	−0.422 (5)	0.315 (4)	0.3240 (7)	0.06*
H9C	−0.182 (5)	0.202 (5)	0.3240 (7)	0.06*
C10	−0.0726 (6)	0.4751 (5)	0.40487 (7)	0.0498 (7)
H12A	−0.171 (5)	0.587 (4)	0.4090 (7)	0.06*
H12B	0.085 (5)	0.526 (4)	0.3995 (7)	0.06*
H12C	−0.061 (5)	0.394 (4)	0.4221 (8)	0.06*
C11	0.2059 (5)	1.0550 (3)	0.49750 (6)	0.0355 (5)
H13	0.293 (4)	1.090 (3)	0.5165 (7)	0.043*
C12	0.2979 (4)	1.0796 (3)	0.46741 (6)	0.0301 (5)
H14	0.438 (4)	1.125 (3)	0.4643 (6)	0.036*
C13	0.1744 (3)	1.0255 (3)	0.44070 (5)	0.0267 (5)
H15	−0.149 (4)	0.920 (3)	0.4274 (6)	0.032*
C14	−0.0465 (4)	0.9489 (3)	0.44428 (6)	0.0334 (5)
H16	−0.292 (4)	0.871 (3)	0.4783 (6)	0.04*
C15	−0.1348 (4)	0.9222 (3)	0.47470 (7)	0.0378 (6)
C16	−0.0119 (4)	0.9739 (3)	0.50166 (6)	0.0351 (5)
C17	−0.1153 (5)	0.9427 (4)	0.53420 (7)	0.0519 (7)
H17A	−0.2793	0.9204	0.5322	0.078*
H17B	−0.0899	1.0513	0.5471	0.078*
H17C	−0.0425	0.8367	0.544	0.078*
N1	−0.1613 (3)	0.3644 (3)	0.37777 (5)	0.0349 (5)
H10	−0.3129	0.3405	0.3812	0.042*
H11	−0.0863	0.2543	0.3775	0.042*
O1	−0.4928 (3)	0.6161 (2)	0.35346 (4)	0.0382 (4)
H6	−0.534 (5)	0.695 (4)	0.3661 (7)	0.046*
O2	0.4535 (3)	0.8834 (3)	0.39905 (5)	0.0478 (5)
O3	0.4268 (4)	1.2203 (3)	0.40278 (5)	0.0573 (6)
O4	0.1095 (3)	1.0419 (3)	0.37990 (4)	0.0461 (5)
S1	0.30178 (10)	1.04466 (8)	0.402484 (15)	0.03374 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0416 (13)	0.0321 (13)	0.0426 (17)	0.0031 (12)	0.0055 (13)	0.0019 (11)
C2	0.0579 (16)	0.0393 (15)	0.058 (2)	0.0061 (15)	0.0222 (16)	0.0111 (13)
C3	0.079 (2)	0.0553 (19)	0.0435 (18)	0.0280 (17)	0.0236 (17)	0.0177 (15)
C4	0.062 (2)	0.073 (2)	0.0341 (19)	0.0215 (17)	−0.0028 (15)	0.0088 (15)
C5	0.0445 (14)	0.0526 (17)	0.0355 (17)	0.0096 (13)	−0.0018 (12)	0.0034 (13)
C6	0.0379 (12)	0.0260 (11)	0.0323 (14)	0.0072 (10)	0.0035 (11)	−0.0016 (9)
C7	0.0301 (12)	0.0299 (12)	0.0313 (14)	0.0007 (9)	0.0012 (10)	−0.0037 (10)
C8	0.0382 (12)	0.0346 (12)	0.0270 (13)	0.0076 (11)	0.0016 (10)	0.0020 (11)
C9	0.080 (2)	0.0324 (14)	0.0375 (18)	0.0119 (15)	−0.0018 (16)	−0.0062 (12)
C10	0.0728 (19)	0.0456 (15)	0.0309 (16)	0.0020 (15)	−0.0108 (15)	−0.0025 (14)
C11	0.0462 (12)	0.0275 (11)	0.0327 (14)	−0.0035 (12)	−0.0027 (11)	−0.0013 (10)
C12	0.0275 (10)	0.0280 (12)	0.0347 (13)	−0.0006 (10)	−0.0009 (11)	0.0004 (9)
C13	0.0284 (10)	0.0218 (10)	0.0300 (13)	0.0027 (10)	0.0015 (9)	0.0003 (9)
C14	0.0305 (11)	0.0272 (12)	0.0425 (16)	0.0012 (11)	−0.0070 (10)	−0.0010 (11)
C15	0.0291 (11)	0.0267 (13)	0.0576 (19)	−0.0019 (10)	0.0089 (11)	0.0031 (11)
C16	0.0456 (12)	0.0216 (10)	0.0381 (15)	0.0072 (11)	0.0115 (11)	0.0005 (10)
C17	0.0703 (17)	0.0332 (13)	0.0523 (19)	−0.0018 (14)	0.0284 (15)	0.0006 (13)
N1	0.0404 (11)	0.0317 (10)	0.0326 (12)	0.0076 (9)	0.0010 (9)	0.0025 (9)
O1	0.0350 (8)	0.0360 (9)	0.0436 (12)	0.0049 (8)	0.0108 (8)	−0.0023 (8)
O2	0.0477 (10)	0.0600 (11)	0.0355 (11)	0.0235 (9)	0.0003 (9)	−0.0105 (9)
O3	0.0794 (14)	0.0495 (11)	0.0431 (13)	−0.0265 (10)	0.0230 (12)	−0.0051 (10)
O4	0.0562 (10)	0.0489 (10)	0.0333 (11)	0.0124 (10)	−0.0097 (8)	−0.0019 (9)
S1	0.0385 (3)	0.0334 (3)	0.0293 (3)	0.0025 (3)	0.0023 (3)	−0.0027 (3)

Geometric parameters (Å, º)

C1—C2	1.385 (4)	C10—H12B	1.00 (3)
C1—C6	1.392 (3)	C10—H12C	0.93 (3)
C1—H1	0.96 (3)	C11—C12	1.383 (3)
C2—C3	1.379 (5)	C11—C16	1.391 (4)
C2—H2	1.01 (3)	C11—H13	0.98 (3)
C3—C4	1.368 (4)	C12—C13	1.384 (3)
C3—H3	1.00 (3)	C12—H14	0.88 (2)
C4—C5	1.388 (4)	C13—C14	1.392 (3)
C4—H4	0.95 (3)	C13—S1	1.771 (2)
C5—C6	1.383 (4)	C14—C15	1.389 (4)
C5—H5	1.02 (3)	C14—H15	0.94 (2)
C6—C7	1.510 (3)	C15—C16	1.386 (4)
C7—O1	1.430 (3)	C15—H16	0.99 (3)
C7—C8	1.530 (3)	C16—C17	1.508 (3)
C7—H7	0.92 (3)	C17—H17A	0.96
C8—C9	1.510 (4)	C17—H17B	0.96
C8—N1	1.512 (3)	C17—H17C	0.96
C8—H8	1.05 (2)	N1—H10	0.9
C9—H9A	0.89 (3)	N1—H11	0.9
C9—H9B	1.03 (3)	O1—H6	0.81 (3)
C9—H9C	0.91 (3)	O2—S1	1.4547 (17)
C10—N1	1.479 (3)	O3—S1	1.4496 (19)
C10—H12A	1.00 (3)	O4—S1	1.4572 (18)
C2—C1—C6	120.4 (3)	H12A—C10—H12C	114 (3)
C2—C1—H1	118.2 (17)	H12B—C10—H12C	110 (2)
C6—C1—H1	121.2 (17)	C12—C11—C16	120.8 (2)
C3—C2—C1	120.3 (3)	C12—C11—H13	121.4 (16)
C3—C2—H2	117.4 (17)	C16—C11—H13	117.7 (15)
C1—C2—H2	122.3 (18)	C11—C12—C13	120.7 (2)
C4—C3—C2	119.3 (3)	C11—C12—H14	122.2 (17)
C4—C3—H3	120.2 (18)	C13—C12—H14	117.0 (16)
C2—C3—H3	120.2 (17)	C12—C13—C14	119.4 (2)
C3—C4—C5	121.3 (3)	C12—C13—S1	120.15 (17)
C3—C4—H4	122 (2)	C14—C13—S1	120.41 (18)
C5—C4—H4	116 (2)	C15—C14—C13	119.2 (2)
C6—C5—C4	119.7 (3)	C15—C14—H15	115.7 (15)
C6—C5—H5	117.3 (16)	C13—C14—H15	125.0 (15)
C4—C5—H5	122.6 (16)	C16—C15—C14	122.0 (2)
C5—C6—C1	119.0 (2)	C16—C15—H16	116.2 (16)
C5—C6—C7	121.8 (2)	C14—C15—H16	121.8 (16)
C1—C6—C7	119.2 (2)	C15—C16—C11	117.9 (2)
O1—C7—C6	113.15 (19)	C15—C16—C17	120.1 (2)
O1—C7—C8	107.02 (19)	C11—C16—C17	122.0 (2)
C6—C7—C8	110.97 (19)	C16—C17—H17A	109.5
O1—C7—H7	111.6 (16)	C16—C17—H17B	109.5
C6—C7—H7	108.8 (16)	H17A—C17—H17B	109.5
C8—C7—H7	105.0 (15)	C16—C17—H17C	109.5
C9—C8—N1	106.6 (2)	H17A—C17—H17C	109.5
C9—C8—C7	113.7 (2)	H17B—C17—H17C	109.5
N1—C8—C7	109.55 (19)	C10—N1—C8	116.1 (2)
C9—C8—H8	113.6 (15)	C10—N1—H10	108.3
N1—C8—H8	106.0 (15)	C8—N1—H10	108.3
C7—C8—H8	107.1 (15)	C10—N1—H11	108.3
C8—C9—H9A	113 (2)	C8—N1—H11	108.3
C8—C9—H9B	110.6 (17)	H10—N1—H11	107.4
H9A—C9—H9B	105 (3)	C7—O1—H6	110 (2)
C8—C9—H9C	112 (2)	O3—S1—O2	113.17 (12)
H9A—C9—H9C	106 (3)	O3—S1—O4	113.18 (13)
H9B—C9—H9C	111 (3)	O2—S1—O4	112.29 (11)
N1—C10—H12A	111.5 (17)	O3—S1—C13	105.33 (11)
N1—C10—H12B	109.5 (18)	O2—S1—C13	106.04 (11)
H12A—C10—H12B	105 (2)	O4—S1—C13	106.03 (11)
N1—C10—H12C	106.8 (19)
C6—C1—C2—C3	−0.8 (4)	C11—C12—C13—C14	1.2 (3)
C1—C2—C3—C4	0.3 (5)	C11—C12—C13—S1	−176.11 (17)
C2—C3—C4—C5	−0.4 (5)	C12—C13—C14—C15	−2.3 (3)
C3—C4—C5—C6	1.0 (5)	S1—C13—C14—C15	175.04 (18)
C4—C5—C6—C1	−1.5 (4)	C13—C14—C15—C16	1.7 (3)
C4—C5—C6—C7	179.8 (2)	C14—C15—C16—C11	0.1 (3)
C2—C1—C6—C5	1.4 (4)	C14—C15—C16—C17	179.8 (2)
C2—C1—C6—C7	−179.8 (2)	C12—C11—C16—C15	−1.2 (3)
C5—C6—C7—O1	−22.8 (3)	C12—C11—C16—C17	179.1 (2)
C1—C6—C7—O1	158.5 (2)	C9—C8—N1—C10	−178.9 (2)
C5—C6—C7—C8	97.5 (3)	C7—C8—N1—C10	−55.5 (3)
C1—C6—C7—C8	−81.2 (3)	C12—C13—S1—O3	−40.2 (2)
O1—C7—C8—C9	60.0 (3)	C14—C13—S1—O3	142.52 (19)
C6—C7—C8—C9	−63.9 (3)	C12—C13—S1—O2	80.06 (19)
O1—C7—C8—N1	−59.2 (2)	C14—C13—S1—O2	−97.26 (19)
C6—C7—C8—N1	176.94 (18)	C12—C13—S1—O4	−160.39 (17)
C16—C11—C12—C13	0.5 (3)	C14—C13—S1—O4	22.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O4^i	0.9	1.9	2.789 (2)	171
N1—H11···S1^i	0.9	2.89	3.663 (2)	145
N1—H10···O3^ii	0.9	1.95	2.789 (3)	154
O1—H6···O2^iii	0.81 (3)	1.94 (3)	2.727 (2)	165 (3)

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

 

Footnotes

‡Current address: TransForm Pharmaceuticals Inc., 29 Hartwell Avenue, Lexington, MA 02139, USA.

¹Supplementary data for this paper, including a complete CIF and ellipsoid plots for all structures determined, are available from the IUCr electronic archives (Reference: BK5025 ). Services for accessing these data are described at the back of the journal.