Supramolecular structures of 1-phenylethylammonium tartrates

The structures of six 1-phenylethylammonium tartrates have been determined and in each of them a distinctive hydrogen-bonded anion substructure can be identified. (S)-1-Phenyl­ethylammonium (R,R)-hydrogen tartrate [(I), P2₁, Z′ = 1] contains anion sheets built from a single type of ring with cations pendent, via three N—H⋯O hydrogen bonds, from just one face of the sheet. (S)-1-Phenylethylammonium rac-hydrogen tartrate [(II), P2₁, Z′ = 2] and its enantiomorph (R)-1-phenylethylammonium rac-hydrogen tartrate [(III), P2₁, Z′= 2] contain anion sheets built from four types of ring, , , and , and there are cations pendent from both faces of the sheet. The anion substructure in bis[(S)-1-phenylethylammonium] (R,R)-tartrate [(IV), P2₁, Z′ = 1] consists of simple C(5) chains, which are linked into sheets by the cations, while in bis(rac-1-phenylethylammonium) (R,R)-tartrate [(V), P2₁, Z′ = 2] there are anion sheets containing two distinct types of ring, with equal numbers of (R) and (S) cations pendent from each face of the anion sheet. Bis[(R)-1-phenylethylammonium] rac-tartrate methanol hemisolvate [(VI), P1, Z′ = 4, with 14 independent components in the asymmetric unit] contains anion sheets built from two types of ring and two types of ring; half of the cations and half of the methanol molecules are pendent from each face of the sheet.

1. Introduction

We have recently reported the supramolecular structures of the tartrate salts formed by a range of simple achiral diamines (Farrell et al., 2002a) and one of the aims of that study was the comparison of cognate pairs of salts formed by the same amine, on the one hand with racemic tartaric acid and on the other with enantiopure (2R,3R)-tartaric acid. In those cases where the racemic and enantiopure acids formed pairs of salts with a common stoichiometry, the overall supramolecular structures of the two salts were very similar, despite their generally different space groups. Moreover, the salts formed by the (2R,3R) acid closely mimic centrosymmetry in a number of cases, a phenomenon also noted in the analogous salts formed by (S)-malic acid with a comparable range of achiral diamines (Farrell et al., 2002b). Another feature of interest in the tartrate structures was the very wide range of anion substructures observed, including a variety of chains of fused rings and a variety of sheet substructures, as well as three-dimensional frameworks of anions encapsulating large voids which enclose the cations.

In view of this variety of anion substructures, but more particularly in view of the common mimicry of centrosymmetry, we have now extended this study to encompass systems in which the amine component is also chiral and for this purpose we have selected 1-phenylethylamine, PhCH(CH₃)NH₂, which is readily available in both enantiopure forms, (R) and (S), as well as in the racemic form. Using the various stereochemical forms of this amine in combination with the various forms of tartaric acid, we have now prepared a range of 1:1 and 2:1 salts (I)–(VI), whose supramolecular structures we discuss here. The structure of (I) has previously been determined using ambient-temperature data (Molins et al., 1989), but no analysis or discussion of the supramolecular aggregation was reported.

2. Experimental

2.1. Synthesis

Samples of racemic 1-phenylethylamine and enantiopure (R)- and (S)-1-phenylethylamine, and of racemic tartaric acid and enantiopure (R,R)-tartaric acid were purchased from Aldrich, and all were used as received. For the preparation of the phenylethylammonium tartrate salts, stoichiometric quantities of the appropriate amine and acid were separately dissolved in methanol. These solutions were then mixed and the mixtures were set aside to crystallize, providing analytically pure samples within a few days. Analyses: found for (I): C 53.1, H 6.7, N 5.1%; for (II): C 53.4, H 6.4, N 5.1%; for (III): C 52.7, H 6.4, N 5.0%: C₁₂H₁₇NO₆ requires C 53.1, H 6.3, N 5.2%: found for (IV): C 60.8, H 7.1, N 6.9%; for (V): C 60.3, H 7.2, N 7.0%; C₂₀H₂₈N₂O₆ requires C 61.2, H 7.2, N 7.1%: for (VI): C 60.1, H 7.4, N 6.8; C₄₁H₆₀N₄O₁₃ requires C 60.3, H 7.4, N 6.9%. For all except (V), satisfactory crystals suitable for single-crystal X-ray diffraction were selected directly from the prepared samples. For (V) the crystals were consistently of poor quality, despite a number of preparations under different conditions, and no useful data were obtained using a conventional laboratory radiation source; however, by use of synchrotron radiation a satisfactory dataset was obtained.

2.2. Data collection, structure solution and refinement

Diffraction data for (I)–(VI) were collected at 150 (1) K using Nonius Kappa-CCD diffractometers with, for (I)–(IV) and (VI), graphite-monochromated Mo Kα radiation (λ = 0.71073 Å) and, for (V), synchrotron radiation (λ = 0.69000 Å). Other details of cell data, data collection and refinement are summarized in Table 1, together with details of the software employed (Farrugia, 1999; Ferguson, 1999; Nonius, 1997; Otwinowski & Minor, 1997; Sheldrick, 1997; Spek, 2003). For (I)–(V) the systematic absences permitted P2₁ and P2₁/m as possible space groups: in each case P2₁ was selected and confirmed by the structure analysis. Crystals of (VI) are triclinic and the space group P1 was selected, and confirmed by the structure analysis. The structures were solved by direct methods and refined with all data on F². A weighting scheme based upon P = [F_o² + 2F_c²]/3 was employed in order to reduce statistical bias (Wilson, 1976). All H atoms were located from difference maps and all were fully ordered. All H atoms were treated as riding atoms with distances C—H 0.95 (aromatic), 0.98 (methyl) or 1.00 (aliphatic CH), N—H 0.91 and O—H 0.84 Å.

Table 1
Experimental details

	(I)	(II)	(III)
Crystal data
Chemical formula	C8H12N·C4H5O6	C8H12N·C4H5O6	C8H12N·C4H5O6
Mr	271.27	271.27	271.27
Cell setting, space group	Monoclinic, P21	Monoclinic, P21	Monoclinic, P21
a, b, c (Å)	6.3425 (2), 13.9448 (3), 7.5021 (3)	7.3025 (2), 22.8901 (11), 8.1193 (3)	7.2952 (2), 22.8935 (11), 8.1100 (3)
α, β, γ (°)	107.6599 (14)	96.599 (2)	96.603 (2)
V (Å^3)	632.25 (4)	1348.19 (9)	1345.49 (9)
Z, Z′	2, 1	4, 2	4, 2
Dx (Mg m^−3)	1.425	1.336	1.339
Radiation type	Mo Kα	Mo Kα	Mo Kα
No. of reflections for cell parameters	1497	3191	9403
θ range (°)	2.9–27.5	2.7–27.7	2.7–27.5
μ (mm^−1)	0.12	0.11	0.11
Temperature (K)	150 (1)	150 (1)	150 (1)
Crystal form, colour	Block, colourless	Needle, colourless	Block, colourless
Crystal size (mm)	0.30 × 0.25 × 0.22	0.28 × 0.16 × 0.14	0.36 × 0.26 × 0.20
Data collection
Diffractometer	Kappa-CCD	Kappa-CCD	Kappa-CCD
Data collection method	φ scans, and ω scans with κ offsets	φ scans, and ω scans with κ offsets	φ scans, and ω scans with κ offsets
Absorption correction	Multi-scan	Multi-scan	Multi-scan
Tmin	0.923	0.584	0.869
Tmax	0.983	0.998	0.991
No. of measured, independent and observed reflections	5067, 1497, 1386	15 852, 3191, 2734	9403, 3160, 2446
Criterion for observed reflections	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)
Rint	0.042	0.129	0.061
θmax (°)	27.5	27.7	27.5
Range of h, k, l	−8 → h → 7	−9 → h → 9	−9 → h → 9
	−17 → k → 18	−29 → k → 29	−27 → k → 29
	−9 → l → 9	−8 → l → 10	−9 → l → 10
Refinement
Refinement on	F^2	F^2	F^2
R[F^2 > 2σ(F^2)], wR(F^2), S	0.032, 0.077, 1.09	0.047, 0.130, 1.06	0.040, 0.091, 1.04
No. of reflections	1497	3191	3160
No. of parameters	177	354	354
H-atom treatment	Constrained to parent site	Constrained to parent site	Constrained to parent site
Weighting scheme	w = 1/[σ^2(Fo^2) + (0.0419P)^2 + 0.0759P], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.0775P], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.0449P)^2 + 0.0771P], where P = (Fo^2 + 2Fc^2)/3
(Δ/σ)max	<0.0001	<0.0001	0.001
Δρmax, Δρmin (e Å^−3)	0.16, −0.20	0.34, −0.24	0.18, −0.21
Extinction method	None	SHELXL	SHELXL
Extinction coefficient	–	0.039 (6)	0.020 (3)

	(IV)	(V)	(VI)
Crystal data
Chemical formula	2C8H12N·C4H4O6	2C8H12N·C4H4O6	4C8H12N·2C4H4O6·CH4O
Mr	392.44	392.44	816.93
Cell setting, space group	Monoclinic, P21	Monoclinic, P21	Triclinic, P1
a, b, c (Å)	5.5620 (2), 16.0630 (3), 11.8260 (4)	8.3381 (14), 22.738 (4), 10.8190 (18)	9.0822 (3), 15.7819 (5), 15.9040 (5)
α, β, γ (°)	90.00, 103.2810 (12), 90.00	90.00, 90.120 (3), 90.00	108.7460 (15), 96.858 (2), 90.0600 (18)
V (Å3)	1028.31 (5)	2051.2 (6)	2141.33 (12)
Z, Z′	2, 1	4, 2	2, 2
Dx (Mg m^−3)	1.267	1.271	1.267
Radiation type	Mo Kα	Synchrotron	Mo Kα
No. of reflections for cell parameters	2434	5818	9771
θ range (°)	3.1–27.5	1.7–29.4	2.6–27.6
μ (mm^−1)	0.09	0.09	0.09
Temperature (K)	150 (1)	150 (1)	150 (1)
Crystal form, colour	Plate, colourless	Plate, colourless	Plate, colourless
Crystal size (mm)	0.36 × 0.26 × 0.10	0.30 × 0.22 × 0.06	0.20 × 0.16 × 0.08
Data collection
Diffractometer	Kappa-CCD	Kappa-CCD	Kappa-CCD
Data collection method	φ scans, and ω scans with κ offsets	φ scans, and ω scans with κ offsets	φ scans, and ω scans with κ offsets
Absorption correction	Multi-scan	Multi-scan	Multi-scan
Tmin	0.877	0.972	0.975
Tmax	0.995	0.994	0.993
No. of measured, independent and observed reflections	8194, 2434, 2187	18 641, 5818, 5504	28 530, 9771, 6899
Criterion for observed reflections	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)
Rint	0.050	0.034	0.094
θmax (°)	27.5	29.4	27.6
Range of h, k, l	−7 → h → 7	−11 → h → 11	−11 → h → 11
	−20 → k → 19	−30 → k → 30	−20 → k → 17
	−14 → l → 15	−15 → l → 14	−19 → l → 20
Refinement
Refinement on	F^2	F^2	F^2
R[F^2 > 2σ(F^2)], wR(F^2), S	0.035, 0.094, 1.05	0.054, 0.151, 1.16	0.051, 0.132, 1.04
No. of reflections	2434	5818	9771
No. of parameters	260	517	1074
H-atom treatment	Constrained to parent site	Constrained to parent site	Constrained to parent site
Weighting scheme	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 0.0872P], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.0842P)^2 + 0.5384P], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.066P)^2], where P = (Fo^2 + 2Fc^2)/3
(Δ/σ)max	<0.0001	0.001	0.001
Δρmax, Δρmin (e Å^−3)	0.22, −0.24	0.59, −0.33	0.44, −0.40
Extinction method	SHELXL	None	SHELXL
Extinction coefficient	0.036 (7)	–	0.0191 (18)
Computer programs used: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PRPKAPPA (Ferguson, 1999).

Supramolecular analyses were made and the diagrams were prepared with the aid of PLATON (Spek, 2003). Details of hydrogen-bond dimensions are given in Table 2.¹ Figs. 1–16 show the ionic components, with the atom-labelling schemes, and aspects of the supramolecular structures.

Table 2
Hydrogen-bond parameters (Å, °)

	D—H⋯A	H⋯A	D⋯A	D—H⋯A
(A) Intra-anion hydrogen bonds
(I)	O5—H5⋯O2	2.11	2.616 (2)	119
	O6—H6⋯O3	2.17	2.652 (2)	116
(III)	O15—H15⋯O12	2.13	2.605 (2)	116
	O25—H25⋯O22	2.11	2.604 (2)	117
(IV)	O5—H5⋯O6	2.46	2.860 (2)	110
	O6—H6⋯O3	2.11	2.603 (2)	117
(V)	None
(VI)	O15—H15⋯O12	2.37	2.661 (4)	101
	O25—H25⋯O22	2.38	2.675 (4)	101
	O45—H45⋯O42	2.38	2.677 (4)	101
(B) Inter-anion hydrogen bonds
(I)	O3—H3⋯O1^i	1.65	2.486 (2)	174
	O5—H5⋯O4^ii	2.18	2.797 (2)	130
(III)	O14—H14⋯O11^iii	1.73	2.568 (2)	176
	O15—H15⋯O22^iv	2.22	2.944 (3)	144
	O16—H16⋯O21	1.92	2.750 (3)	170
	O24—H24⋯O21^ii	1.74	2.575 (2)	177
	O25—H25⋯O12^i	2.35	3.019 (3)	136
	O26—H26⋯O11	1.94	2.773 (3)	169
(IV)	O5—H5⋯O1^iii	2.07	2.882 (2)	161
(V)	O15—H15⋯O22^iii	1.91	2.743 (3)	169
	O16—H16⋯O23^iv	1.87	2.690 (3)	164
	O25—H25⋯O11	1.86	2.681 (3)	167
	O26—H26⋯O13^v	1.91	2.743 (3)	169
(VI)	O16—H16⋯O21	1.90	2.722 (4)	167
	O26—H26⋯O11	1.89	2.712 (4)	168
	O36—H36⋯O41	1.91	2.741 (4)	171
	O46—H46⋯O31	1.88	2.711 (4)	171
	O15—H15⋯O34^ii	1.84	2.628 (4)	156
	O25—H25⋯O44^vi	1.82	2.584 (4)	150
	O35—H35⋯O14	1.83	2.617 (4)	156
	O45—H45⋯O24^vii	1.82	2.585 (4)	150
(C) Cation–anion hydrogen bonds
(I)	N1—H1A⋯O1	2.00	2.901 (2)	172
	N1—H1B⋯O5^viii	2.02	2.867 (2)	154
	N1—H1C⋯O2^iii	1.93	2.842 (2)	177
(III)	N3—H3A⋯O26^iv	2.11	2.945 (3)	152
	N3—H3A⋯O23^iv	2.35	2.893 (3)	118
	N3—H3B⋯O15^ii	1.96	2.847 (3)	165
	N3—H3C⋯O12	1.85	2.747 (3)	167
	N4—H4A⋯O16^i	2.15	2.956 (3)	147
	N4—H4A⋯O13^i	2.25	2.916 (3)	129
	N4—H4B⋯O25^iii	1.93	2.824 (3)	169
	N4—H4C⋯O22	1.87	2.752 (3)	162
(IV)	N1—H1A⋯O2^ix	1.88	2.759 (2)	161
	N1—H1B⋯O4	1.93	2.823 (2)	167
	N1—H1C⋯O1^x	1.89	2.745 (2)	155
	N2—H2A⋯O2	1.84	2.746 (2)	172
	N2—H2B⋯O2^x	1.91	2.774 (2)	158
	N2—H2C⋯O3^ii	1.85	2.720 (2)	159
(V)	N3—H3A⋯O12	1.90	2.801 (3)	171
	N3—H3B⋯O22	1.82	2.718 (4)	168
	N3—H3C⋯O14^ii	1.89	2.777 (3)	165
	N4—H4A⋯O23^viii	1.85	2.738 (3)	165
	N4—H4B⋯O12^iii	1.92	2.825 (3)	170
	N4—H4C⋯O14	1.98	2.798 (3)	149
	N5—H5A⋯O21^viii	1.89	2.774 (3)	164
	N5—H5B⋯O24^iv	1.89	2.798 (3)	173
	N5—H5C⋯O13	1.83	2.716 (3)	164
	N6—H6A⋯O24	1.95	2.847 (3)	171
	N6—H6B⋯O21^iii	1.96	2.803 (3)	154
	N6—H6C⋯O11	1.86	2.747 (3)	164
(VI)	N5—H5A⋯O23^vii	1.98	2.885 (4)	171
	N5—H5B⋯O22^xi	1.99	2.882 (4)	168
	N5—H5C⋯O46	2.00	2.902 (4)	173
	N6—H6A⋯O45	2.10	2.973 (4)	161
	N6—H6B⋯O22^xi	1.96	2.858 (4)	169
	N6—H6C⋯O11^vii	1.89	2.768 (4)	160
	N7—H7A⋯O43^iii	2.01	2.898 (4)	167
	N7—H7B⋯O42	1.95	2.859 (4)	173
	N7—H7C⋯O26^vii	2.00	2.906 (4)	178
	N8—H8A⋯O33^ii	1.93	2.822 (4)	168
	N8—H8B⋯O16	2.03	2.912 (4)	163
	N8—H8C⋯O32	1.96	2.869 (4)	175
	N9—H9A⋯O41^ii	1.93	2.832 (4)	169
	N9—H9B⋯O32	2.00	2.891 (4)	167
	N9—H9C⋯O15	1.92	2.825 (4)	174
	N10—H10A⋯O36	2.04	2.920 (4)	162
	N10—H10B⋯O12^iii	1.95	2.852 (4)	173
	N10—H10C⋯O13	1.93	2.819 (4)	165
	N11—H11A⋯O42^xii	1.96	2.863 (4)	171
	N11—H11B⋯O31^vi	1.91	2.781 (4)	160
	N11—H11C⋯O25	2.03	2.918 (4)	163
	N12—H12A⋯O21	1.93	2.832 (4)	170
	N12—H12B⋯O12^iii	2.00	2.906 (4)	172
	N12—H12C⋯O35	1.94	2.844 (4)	177
(D) Cation–cation hydrogen bonds
(III)	C36—H36⋯Cg^ix†	2.87	3.775 (3)	160
(E) Solvent–anion hydrogen bonds
(VI)	O1—H1⋯O23	1.90	2.730 (5)	170
	O2—H2⋯O43	1.97	2.791 (5)	164
Symmetry codes: (i) x, y, -1 +z; (ii) -1 + x, y, z; (iii) 1 + x, y, z; (iv) x, y, 1 + z; (v) -1 + x, y, -1 + z; (vi) x, -1 + y, z; (vii) 1 + x, 1 + y, z; (viii) 1 + x, y, 1 + z; (ix) ; (x) ; (xi) x, 1 + y, z; (xii) -1 + x, -1 + y, z.

†Cg represents the ring centroid of the ring C41–C46.

Figure 1 The independent components of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2 The independent components of (III) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 3 The independent components of (IV) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 4 The independent components of (V) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 5 The independent components of (VI) showing the atom-labelling scheme: (a) the four independent anions and the two methanol molecules; (b)–(i) the eight independent cations. Displacement ellipsoids are drawn at the 30% probability level.

Figure 6 Part of the crystal structure of (I) showing the formation of a (010) sheet of anions with cations pendent from it. For the sake of clarity, the H atoms bonded to the C atoms are omitted, as are the phenyl and methyl groups in the cation. The atoms marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&) are at the symmetry positions (x, y, -1 + z), (-1 + x, y, z), (1 + x, y, z) and (1 + x, y, 1 + z), respectively.

Figure 7 Part of the crystal structure of (III), showing the formation by the anions of a (010) sheet containing four different types of ring. For the sake of clarity, the H atoms bonded to the C atoms are omitted, as are the intra-anion O—H⋯O hydrogen bonds. The atoms marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&) are at the symmetry positions (x, y, 1 + z), (x, y, -1 + z), (1 + x, y, z) and (-1 + x, y, z), respectively.

Figure 8 Part of the crystal structure of (IV) showing the formation of the C(5) anion chains parallel to [100] and their linking into (001) sheets by the cations. For the sake of clarity, the H atoms bonded to the C atoms are omitted, as are the methyl and phenyl groups in the cations and the intra-anion O—H⋯O hydrogen bonds. The atoms marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&) are at the symmetry positions (-1 + x, y, z), (1 + x, y, z), () and (), respectively.

Figure 9 Part of the crystal structure of (V) showing the formation of a (010) anion sheet built from two types of ring. For the sake of clarity, the H atoms bonded to C atoms are omitted. The atoms marked with an asterisk (*), a hash (#) or a dollar sign ($) are at the symmetry positions (x, y, 1 + z), (1 + x, y, z) and (-1 + x, y, -1 + z), respectively.

Figure 10 Part of the crystal structure of (VI) showing the formation of a (001) anion sheet built from two types of ring and two types of ring. For the sake of clarity the H atoms bonded to C atoms are omitted, as are the methyl and phenyl groups in the cations and the intra-anion O—H⋯O hydrogen bonds. The atoms marked with an asterisk (*), a hash (#) or a dollar sign ($) are at the symmetry positions (-1 + x, y, z), (x, -1 + y, z) and (1 + x, 1 + y, z), respectively.

Figure 11 Stereoview of part of the crystal structure of (I) showing the cations pendent from a single face of the anion sheet. For the sake of clarity, the H atoms bonded to the C atoms have been omitted.

Figure 12 Projection of part of the crystal structure of (III) showing the tripartite (010) layers with cations linked to both faces of the anion sheet. For the sake of clarity, the H atoms bonded to the C atoms have been omitted.

Figure 13 Projection of part of the crystal structure of (V) showing one of the tripartite (010) layers with cations linked to both faces of the anion sheet. For the sake of clarity, the H atoms bonded to C atoms have been omitted.

Figure 14 Stereoview of part of the crystal structure of (VI) showing the tripartite sheets and the pendent methanol molecules. For the sake of clarity, the H atoms bonded to C atoms have been omitted.

Figure 15 Projection of part of the crystal structure of (IV) showing the cations linked to both faces of the anion sheet, and the action of the 21 screw axes in causing alternation of the cations between the two faces. For the sake of clarity, the H atoms bonded to C atoms have been omitted.

Figure 16 Stereoview of part of the crystal structure of (III) showing the [010] chain built from C—H⋯π(arene) hydrogen bonds which links the (010) sheets. For the sake of clarity the H atoms not involved in the motif shown have been omitted.

3. Results and discussion

3.1. Crystallization characteristics

Crystallization from methanol solutions of equimolar mixtures of 1-phenylethylamine and tartaric acid gives, regardless of whether the compounds are enantiopure or racemic mixtures, salts of the composition [PhCH(CH₃)NH₃]⁺·[HOCOCH(OH)CH(OH)COO]⁻, in which complete transfer of a single H atom from the acid component to the basic components has occurred.

When enantiopure (S)-amine was cocrystallized with enantiopure (R,R)-acid, the salt (I) was produced in which the asymmetric unit (Fig. 1) consists of just one cation and one anion. The identical salt was identified as the sole crystalline product from the cocrystallization of the racemic amine and the enantiopure (R,R)-acid, so that complete enantioselectivity in crystallization is apparent with no (R) configuration cations present in the crystalline salt. It is of interest to note in this context that no crystalline product of consistent composition could be obtained from cocrystallizations of enantiopure (R)-amine with enantiopure (R,R)-acid: this observation is entirely consistent with the behaviour reported by Molins et al. (1989), who were also unable to obtain any crystalline product from this combination of amine and acid.

On the other hand, when the enantiopure (S)-amine was cocrystallized with racemic tartaric acid, the product (II) was found to have an asymmetric unit containing two cations, both of (S) configuration, and two anions, one each of (R,R) and (S,S) configuration. The enantiomorphous compound (III) was obtained from enantiopure (R)-amine and the racemic acid. Hence, although the enantiopure acid exerts selectivity on the racemic amine in the formation of (I), the enantiopure amine has not exerted any selectivity in the formation of (II) and (III). The refinement for (III) is rather better than that for (II) and hence we discuss only (III) (Fig. 2) hereafter.

When the initial crystallization mixtures contained a 2:1 molar ratio of amine to acid, the resulting salts all had the composition [{PhCH(CH₃)NH₃}⁺]₂·[OOCCH(OH)CH(OH)­COO]²⁻, again regardless of whether enantiopure or racemic components were employed. Cocrystallization of such a 2:1 mixture containing enantiopure (S)-amine and enantiopure (R,R)-acid yielded a product (IV) containing two cations and one anion in the asymmetric unit (Fig. 3). In contrast to the behaviour of the 1:1 mixture producing (I), a 2:1 mixture of racemic amine and enantiopure (R,R)-acid gave a product (V) in which the asymmetric unit (Fig. 4) consists of four cations, two each of (R) and (S) configurations, and two anions, so that no enantioselectivity is apparent here.

Each of the salts (I)–(V) crystallizes in the space group P2₁. However, the salt (VI) produced from a 2:1 mixture of enantiopure (R)-amine and racemic tartaric acid crystallizes in the space group P1 and its asymmetric unit (Fig. 5) contains eight cations and four anions, of which two each have (R,R) and (S,S) configurations, together with two methanol molecules. A product (VII) of identical composition was isolated from a 2:1 mixture of the enantiopure (S)-amine and racemic tartaric acid, but no crystals suitable for single-crystal X-ray diffraction have yet been obtained.

3.2. Structure solutions

Although in each of (I)–(VI) the Flack parameter (Flack, 1983) was wholly inconclusive (Flack & Bernardinelli, 2000) because of the very low anomalous dispersion characteristic of the light elements C, N and O, nonetheless, in every case the initial structure solution, obtained using System-S in PLATON (Spek, 2003), corresponded to the correct enantiomorph of the enantiopure component present.

Struck by this rather unexpected result, we have now reviewed our initial structure solutions for some recently completed series of light-atom structures containing enantiopure components of previously known configuration, namely series containing malate and tartrate anions (Farrell et al., 2002a,b; Bowes et al., 2003b; Turkington et al., 2004). In a total of 17 structures, including those reported here, each having a chiral space group containing an enantiopure component of previously known configuration, the initial structure solution using System-S gave the correct enantiomorph in every case, without exception.

3.3. Intra-anion hydrogen bonds

The intra-anion hydrogen bonding (Table 2), in principle the simplest aspect of the hydrogen bonding, nonetheless shows several variants, several of which are not readily predictable. In the independent anion of (III), and in three of the four independent anions in (VI), there is a single intra-anion hydrogen bond and in every case the acceptor is a carboxylate O atom. In the fourth anion in (VI), no such bond occurs nor is there any such bond in either of the anions in (V). In (I) and (IV), on the other hand, both hydroxyl groups in the anion form intra-anion hydrogen bonds; in (I) both acceptors are carboxyl O atoms, while for (III) the acceptor in one interaction is a carboxylate O, as usual, while in the other it is the second hydroxyl O. For none of these hydrogen bonds does the O—H⋯O angle exceed 120°, so that the interaction energies may well be fairly small: however, the entropic cost of these interactions is almost negligible and they may well have a significant influence on the overall anion conformations.

3.4. Anion substructures

In the supramolecular structures of each of (I)–(VI) there is a clearly identifiable substructure built from only the anions. It is convenient to approach the overall analysis of the supramolecular structures firstly in terms of these anion substructures and then to consider how the cations, and in (VI) only the methanol molecules, are linked to the anion substructure.

3.4.1. Compound (I)

The anions in (I) form a two-dimensional substructure which is generated wholly by translation. Carboxyl O3 in the anion at (x, y, z) acts as a donor to carboxylate O1 in the anion at (x, y, -1 + z) in a very short hydrogen bond, so generating a C(7) (Bernstein et al., 1995) chain running parallel to the [001] direction. The hydroxyl O5, as well as acting as a hydrogen-bond donor to O2 within the anion, also acts as a donor to carbonyl O4 in the anion at (-1 + x, y, z), in a planar three-centre O—H⋯(O)₂ system, so generating a C(6) chain parallel to [100]. The combination of the [100] and [001] chains generates a (010) sheet in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of ring (Fig. 6). The reference anion sheet lies in the domain 0.27 < y < 0.47 and a second such sheet, related to the first by the action of the 2₁ screw axis, lies in the domain 0.77 < y < 0.97.

3.4.2. Compound (III)

The two independent anions in (III) form a two-dimensional substructure which is generated wholly by translation. Within the asymmetric unit (Fig. 2), hydroxyl atoms O16 and O26 act as hydrogen-bond donors, respectively, to carboxylate atoms O21 and O11, and these dimers are linked by two further pairs of O—H⋯O hydrogen bonds into chains of edge-fused rings running along the [100] and [001] directions. Carboxyl atoms O14 and O24 in the anion pair at (x, y, z) act as donors, respectively, to carboxylate atoms O11 at (1 + x, y, z) and O21 at (-1 + x, y, z), thereby generating by translation a chain of edge-fused, alternating and rings, in which the carboxylate atoms O11 and O21 both act as double acceptors of O—H⋯O hydrogen bonds. In addition, the two hydroxyl atoms O15 and O25 at (x, y, z) act as donors, respectively, to carboxylate atoms O22 at (x, y, 1 + z) and O12 at (x, y, -1 + z), thereby generating by translation a second chain of edge-fused rings, this time running parallel to the [001] direction and containing alternating and rings. The combination of the [100] and [001] chains generates a (010) sheet built from four different types of ring, , , and (Fig. 7). The first two ring types each involve one (2R,3R) anion and one (2S,3S) anion, while the latter two types involve two anions of each hand; each ring is therefore approximately, but not crystallographically, centrosymmetric. The hydrogen-bonded anion sheet is modestly reinforced by an antiparallel and nearly centrosymmetric carbonyl–carbonyl interaction involving the groups C14=O13 and C24=O23 in the anions at (x, y, z) and (1 + x, y, z), respectively. The distances O13⋯C14ⁱ and C14⋯O23ⁱ [symmetry code (i) 1 + x, y, z] are 2.887 (3) and 2.865 (3) Å, respectively, with angles C14—O13⋯C24ⁱ and C14⋯O23ⁱ—C24ⁱ of 92.9 (2) and 94.2 (2)°, respectively, hence forming an almost ideal type-II interaction (Allen et al., 1998). The reference anion sheet lies in the domain 0.38 < y < 0.59, with the anion dimers all centred at around y = 0.50; the immediately adjacent sheets, related to the first by the action of the 2₁ screw axis, lie in the domain −0.12 < y < 0.09 and 0.88 < y < 1.09, with their anion dimers centred at around y = 0.0 and y = 1.0, respectively.

3.4.3. Compound (IV)

The anion substructure of (IV) consists of simple chains generated by translation. The hydroxyl atom O5 in the anion at (x, y, z) acts as a hydrogen-bond donor to the carboxylate atom O1 in the anion at (1 + x, y, z), so generating by translation a C(5) chain running parallel to the [100] direction (Fig. 8). This chain lies in the domain 0.54 < y < 0.85, and a second chain, related to the first by the action of the 2₁ screw axis, lies in the domain 0.04 < y < 0.35: the [100] chains are linked into sheets by the two types of cation.

3.4.4. Compound (V)

In (V) there are two independent tartrate anions, albeit both with the (R,R) configuration, and there are four independent O—H⋯O hydrogen bonds which link the anions into sheets generated by translation. With the asymmetric unit (Fig. 4), the hydroxyl atom O25 acts as a hydrogen-bond donor to the carboxylate atom O11. The hydroxyl atom O15 in the anion pair at (x, y, z) acts as a donor to the carboxylate atom O22 in the anion pair at (1 + x, y, z), thus generating by translation a C₂²(10) chain running parallel to the [100] direction. Similarly, the hydroxyl atom O16 at (x, y, z) acts as a donor to the carboxylate atom O23 at (x, y, 1 + z), so generating a second chain by translation, this time of C22(12) type and running parallel to the [001] direction. Finally, the hydroxyl atom O26 at (x, y, z) acts as a donor to the carboxylate atom O13 at (-1 + x, y, -1 + z), thus generating by translation a second C₂²(12) motif, now running parallel to the [101] direction. The combination of these three translational chain motifs generates a (010) sheet of anions characterized by two different types of ring (Fig. 9).

This reference sheet of anions lies within the domain 0.42 < y < 0.59 and a second such sheet, related to the first by the action of the 2₁ screw axes, lies in the domain −0.08 < y < 0.09. The large spaces between the nearly planar anion layers are occupied by the cations.

3.4.5. Compound (VI)

Despite the presence of 14 independent components in the asymmetric unit of (VI) (Fig. 5), the four independent anions together generate a fairly simple two-dimensional substructure, from which all of the other components, both cations and neutral methanol molecules, are pendent.

Within the anion sheet there are eight independent inter-anion O—H⋯O hydrogen bonds all involving hydroxyl O as the donor and carboxylate O as the acceptor. Four of these hydrogen bonds link pairs of anions, each comprising one (R,R) anion and one (S,S) anion, into two almost centrosymmetric dimers, and the other four O—H⋯O hydrogen bonds link the dimers into a continuous sheet. Atoms O16 and O26 act as donors, respectively, to atoms O21 and O11, thus generating a nearly centrosymmetric dimer, which we denote as the type A dimer, whose centroid is close to (0.25, 0.25, 0.5): similarly, atoms O36 and O46 act as donors, respectively, to atoms O41 and O31, thus generating a second nearly centrosymmetric dimer, denoted as type B, whose centroid is close to (0.75, 0.75, 0.5).

The inter-dimer hydrogen bonds are so arranged that each type A dimer acts as a donor to two type B dimers and as an acceptor from two further type B dimers, while each type B dimer is similarly linked to four different type A dimers. Thus, for example, in the type A dimer at approximately (0.25, 0.25, 0.5), atoms O25 and O15 act as donors, respectively, to the atoms O44 at (x, -1 + y, z) and O34 at (-1 +x, y, z), which lie in the type B dimers at approximately (0.75, −0.25, 0.5) and (−0.25, 0.75, 0.5), respectively: similarly, atoms O14 and O24 in the type A dimer at approximately (0.25, 0.25, 0.5) accept hydrogen bonds, respectively, from atoms O35 at (x, y, z) and O45 at (-1 + x, -1 + y, z), which lie in the type B dimers at approximately (0.75, 0.75, 0.5) and (−0.25, −0.25, 0.5), respectively. In this manner, the two types of dimer are linked into a (001) sheet containing two independent rings within the dimers and two independent rings between the dimers. If the individual anions are taken to be the nodes of the resulting net, this is of the (6,3) type (Batten & Robson, 1998), while if the pseudosymmetric dimers are taken as the nodes the net is of the (4,4) type (Fig. 10). Just one sheet of this type passes through each unit cell, occupying only about one-third of the domain of z: for the selected location of the asymmetric unit, the sheet occupies the domain 0.34 < z < 0.68.

3.5. Linking of the cations to the anion substructures

In each of (I), (III), (V) and (VI) the cations are linked to anion sheets, whereas in (IV) the cations link anion chains into sheets; it is convenient to discuss these two structure types separately. In each of these compounds the [PhCH(CH₃)NH₃]⁺ cations act as threefold donors in N—H⋯O hydrogen bonds and each cation is linked to three different anions (Table 2): the majority of these hydrogen bonds are of two-centre type, but three-centre N—H⋯(O)₂ systems occur in (III)

3.5.1. Compounds (I), (III), (V) and (VI)

In each of these compounds the three anions which are directly hydrogen-bonded to a given cation form part of the same sheet: however, the orientation of the organic parts of the cations is not the same in each compound. The cations in (I) are all of the (S) configuration and all are hydrogen-bonded to just one face of the anion sheet (Fig. 6), so that viewed along the plane of the anion sheet the structure appears to consist of alternating slabs of cations and anions (Fig. 11). In (III), by contrast, there are cations pendent from both faces of the anion sheet (Fig. 7), although all have the same (R) configuration, with all of the type 1 cations containing N3 pendent from one face and all of the type 2 containing N4 cations pendent from the opposite face. Hence, each (010) layer is tripartite with a polar central layer containing all the hydrogen bonds and two lipophilic outer layers (Fig. 12).

In (V) the cations are again pendent from both faces of the anion sheet (Fig. 9), however, there are cations of both (R) and (S) configurations bonded to both faces. The cations containing N3 and N4, which have the (R) and (S) configurations, respectively, are pendent from one face, while the cations containing N5 and N6, again of (R) and (S) configurations, respectively, are pendent from the opposite face: hence, a tripartite layer is again generated (Fig. 13). All of the cations in (VI) have the (R) configuration and four cations are pendent from each face of the sheet: those containing N5, N8, N1 and N12 are pendent from one face, and those containing N6, N7, N9 and N10 are pendent from the other face (Fig. 14).

3.5.2. Compound (IV)

The anion substructure in (IV) consists of simple [100] chains generated by translation and the action of the cations is to link these chains into sheets, while the action of the 2₁ screw axes is to cause an alternation of each type of cation, both of (S) configuration, between the two faces of these sheets.

The ammonium atom N1 at (x, y, z) acts as a hydrogen-bond donor, via H1B, to atom O4 in the anion at (x, y, z), which lies in the reference [100] chain, and via H1A and H1C to atoms O2 in the anion at () and O1 in the anion at ), both of which lie in an adjacent [100] chain related to the first chain by the action of the 2₁ screw axes. Atom N2 at (x, y, z) acts as a donor, via H2A and H2C, to atoms O4 in the anion at (x, y, z) and O3 in the anion at (-1 + x, y, z), respectively, which both lie in the reference anion chain, and via H2B, to atom O2 in the anion at (), which lie in the adjacent chain referred to previously. In this way the two cations at (x, y, z) are each hydrogen bonded to the same pair of anion chains and propagation of these interactions by the 2₁ screw axes then links the anion chains and the cations into a (001) sheet (Fig. 8). The reference cations containing N1 and N2 have their PhCH(CH₃)— fragments on opposite sides of the sheet, but the action of the screw axes means that there are equal numbers of each of the two cation types on both sides of the sheet (Fig. 15).

3.6. Linking of the sheets in (III)

In none of the compounds described here are there any aromatic π⋯π stacking interactions, but in (III) only there is a single C—H⋯π(arene) hydrogen bond, whose effect is to link the adjacent tripartite (010) sheets into a continuous framework structure. The aromatic atom C36 in the type 1 cation at (x, y, z), which is pendent from the anion sheet in the domain 0.38 < y < 0.59, acts as a hydrogen-bond donor to the ring C41–C46 in the type 2 cation at (), which is pendent from the anion sheet in the domain −0.12 < y < 0.09, so forming a chain running parallel to the [010] direction and generated by the 2₁ screw axis along (0.5, y, 0.5), which serves to link each (010) sheet to the two adjacent sheets (Fig. 16).

3.7. (S)-1-Phenylethylammonium meso-hydrogen tartrate

This compound crystallizes in the space group P2₁ in a unit cell very similar to that of (I) (Table 1), but with the anion in an almost centrosymmetric configuration (Kroon et al., 1984): although no analysis of the supramolecular structure appears in this report, the reported atom coordinates indicate both similarities to, and differences from, that of (I). As in (I), the anions are linked into hydrogen-bonded (010) sheets and the cations are pendent from just one face of this sheet. However, whereas in (I) the sheets contain just a single type of ring, in the meso-tartrate analogue the sheets contain alternating and rings.

3.8. (R)-Histidinium (R,R)-hydrogen tartrate

The supramolecular structure of (R)-histidinium (R,R)-hydrogen tartrate has been reported very recently (Johnson & Feeder, 2004). In this salt, which crystallizes in the space group P1 with Z′ = 1, the anions form (010) sheets of , formed in a manner entirely similar to those in (I) (see §3.4.1), with one-dimensional substructures in the form of C(6) and C(7) chains along [100] and [010], respectively, although in (I) the C(7) chain is parallel to [001]. The principal difference between the structure of (I) and that of (R)-histidinium (R,R)-hydrogen tartrate arises from the hydrogen-bonding characteristics of the cations. In (I) the cation is a threefold donor in N—H⋯O hydrogen bonds, whereas in (R)-histidinium (R,R)-hydrogen tartrate the cation is a fivefold donor (although not all of the N—H⋯O hydrogen bonds are listed in Table 2 of Johnson & Feeder, 2004), and the action of the cation is to link the anion sheets into a continuous three-dimensional framework.

4. Concluding comments

For both the 1:1 salts (I)–(III) and the 2:1 salts (IV)–(VI) described here, modest changes in the stereochemical nature of the components provokes rather considerable changes in the crystallization characteristics, as manifested by a comparison of both the unit-cell dimensions and the Z′ values within each series (Table 1). At a more detailed level, no two salts described here, apart from the enantiomorphous pair (II) and (III), have a common anion substructure, and it is notable that we have not observed in any of (I)–(VI) any three-dimensional anion substructures as observed in the 1:2 salts formed by racemic tartaric acid with each of the simple achiral diamines piperazine and 1,4-diazabicycle[2.2.2]octane (Farrell et al., 2002a). In the present series, even when the anion sub-structures are two-dimensional, the variety and the sizes of the hydrogen-bonded rings from which the sheets are built are different in every case. We have previously observed very marked diversity of supramolecular aggregation in series involving geometrical (constitutional) as opposed to setereochemical (configurational) isomerism (Bowes et al., 2003a; Glidewell et al., 2002, 2004). In the salts (I) and (IV), where both components are enantiopure, there is no hint of any mimicry of pseudosymmetry (Figs. 11 and 15). However, in the salts (II), (III) and (VI), where the cations are enantiopure and the anions are racemic, there is strong mimicry of centrosymmetry (Figs. 12 and 14), with weaker indications in (V) (Fig. 9). In general, pseudo-symmetry seems to be manifest in the present series when the anions are racemic, indicating that the formation of the anion sub-structure is a major determinant of the supramolecular structure as a whole.

Supporting information

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures

In full text version.

(I) (S)-1-Phenylethylammonium (R,R)-tartrate(1-)

Crystal data

C8H12N·C4H5O6	F(000) = 288
Mr = 271.27	Dx = 1.425 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1497 reflections
a = 6.3425 (2) Å	θ = 2.9–27.5°
b = 13.9448 (3) Å	µ = 0.12 mm^−1
c = 7.5021 (3) Å	T = 150 K
β = 107.6599 (14)°	Block, colourless
V = 632.25 (4) Å^3	0.30 × 0.25 × 0.22 mm
Z = 2

Data collection

Kappa-CCD diffractometer	1497 independent reflections
Radiation source: fine-focus sealed X-ray tube	1386 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −8→7
Tmin = 0.923, Tmax = 0.983	k = −17→18
5067 measured reflections	l = −9→9

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0419P)^2 + 0.0759P] where P = (Fo^2 + 2Fc^2)/3
1497 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2960 (2)	0.42472 (12)	0.49188 (18)	0.0220 (3)
O2	−0.0698 (2)	0.42427 (12)	0.34959 (19)	0.0221 (3)
O3	0.2124 (2)	0.37822 (11)	−0.21678 (19)	0.0212 (3)
O4	0.5036 (2)	0.47083 (12)	−0.0727 (2)	0.0244 (3)
O5	−0.0345 (2)	0.47002 (12)	0.02165 (18)	0.0235 (3)
O6	0.2191 (3)	0.29349 (10)	0.1013 (2)	0.0244 (3)
C1	0.1254 (3)	0.43361 (14)	0.3506 (2)	0.0166 (4)
C2	0.1674 (3)	0.46078 (15)	0.1664 (2)	0.0162 (4)
C3	0.3147 (3)	0.38611 (14)	0.1132 (3)	0.0176 (4)
C4	0.3549 (3)	0.41584 (14)	−0.0696 (2)	0.0167 (4)
N1	0.7490 (3)	0.49259 (12)	0.6287 (2)	0.0186 (3)
C11	0.6050 (3)	0.64562 (14)	0.4699 (3)	0.0205 (4)
C12	0.6329 (4)	0.63511 (16)	0.2939 (3)	0.0238 (4)
C13	0.4879 (4)	0.67869 (17)	0.1382 (3)	0.0281 (5)
C14	0.3139 (4)	0.73371 (16)	0.1562 (4)	0.0313 (5)
C15	0.2835 (4)	0.74412 (17)	0.3315 (4)	0.0314 (5)
C16	0.4288 (4)	0.70078 (15)	0.4866 (3)	0.0256 (5)
C17	0.7625 (3)	0.60055 (15)	0.6422 (3)	0.0201 (4)
C18	1.0021 (4)	0.63048 (16)	0.6751 (3)	0.0256 (5)
H3	0.2491	0.3916	−0.3125	0.032*
H5	−0.1403	0.4600	0.0647	0.035*
H6	0.1607	0.2789	−0.0115	0.037*
H2	0.2454	0.5240	0.1836	0.019*
H3A	0.4605	0.3850	0.2135	0.021*
H1A	0.6047	0.4741	0.5963	0.028*
H1B	0.8238	0.4665	0.7413	0.028*
H1C	0.8102	0.4721	0.5403	0.028*
H12	0.7523	0.5978	0.2802	0.029*
H13	0.5082	0.6707	0.0187	0.034*
H14	0.2159	0.7642	0.0498	0.038*
H15	0.1631	0.7810	0.3446	0.038*
H16	0.4080	0.7088	0.6059	0.031*
H17	0.7172	0.6208	0.7532	0.024*
H18A	1.0502	0.6107	0.5682	0.038*
H18B	1.0959	0.5997	0.7891	0.038*
H18C	1.0145	0.7003	0.6893	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0191 (7)	0.0337 (7)	0.0131 (6)	−0.0020 (6)	0.0049 (5)	0.0015 (6)
O2	0.0191 (7)	0.0332 (7)	0.0165 (6)	0.0014 (6)	0.0091 (5)	0.0010 (6)
O3	0.0209 (7)	0.0307 (8)	0.0131 (6)	−0.0044 (6)	0.0069 (5)	0.0007 (6)
O4	0.0218 (7)	0.0331 (8)	0.0200 (7)	−0.0061 (6)	0.0089 (6)	−0.0010 (6)
O5	0.0148 (7)	0.0407 (8)	0.0149 (7)	0.0045 (6)	0.0045 (5)	0.0055 (6)
O6	0.0350 (9)	0.0202 (7)	0.0205 (7)	−0.0021 (6)	0.0120 (7)	0.0011 (6)
C1	0.0197 (9)	0.0180 (9)	0.0132 (8)	0.0002 (7)	0.0067 (7)	−0.0012 (8)
C2	0.0152 (8)	0.0213 (9)	0.0121 (8)	−0.0001 (7)	0.0043 (7)	0.0017 (7)
C3	0.0166 (9)	0.0223 (9)	0.0150 (9)	0.0008 (8)	0.0065 (7)	0.0009 (8)
C4	0.0150 (8)	0.0218 (9)	0.0140 (8)	0.0024 (8)	0.0053 (7)	0.0011 (8)
N1	0.0166 (8)	0.0219 (8)	0.0179 (8)	0.0001 (7)	0.0062 (6)	0.0023 (7)
C11	0.0181 (10)	0.0183 (9)	0.0248 (10)	−0.0015 (7)	0.0064 (8)	0.0010 (8)
C12	0.0222 (10)	0.0249 (10)	0.0246 (10)	−0.0002 (8)	0.0074 (8)	0.0034 (8)
C13	0.0289 (11)	0.0284 (11)	0.0241 (10)	−0.0057 (9)	0.0038 (9)	0.0047 (10)
C14	0.0237 (11)	0.0249 (11)	0.0377 (12)	−0.0029 (10)	−0.0018 (9)	0.0103 (10)
C15	0.0215 (11)	0.0227 (10)	0.0462 (13)	0.0045 (9)	0.0045 (10)	0.0012 (10)
C16	0.0208 (10)	0.0229 (11)	0.0327 (11)	−0.0006 (8)	0.0074 (9)	−0.0038 (9)
C17	0.0205 (10)	0.0201 (10)	0.0203 (10)	0.0005 (8)	0.0070 (8)	−0.0014 (8)
C18	0.0206 (10)	0.0278 (11)	0.0261 (10)	−0.0030 (8)	0.0035 (8)	−0.0020 (9)

Geometric parameters (Å, º)

O1—C1	1.270 (2)	C11—C12	1.392 (3)
O2—C1	1.243 (2)	C11—C16	1.393 (3)
O3—C4	1.306 (2)	C11—C17	1.510 (3)
O3—H3	0.84	C12—C13	1.389 (3)
O4—C4	1.221 (2)	C12—H12	0.95
O5—C2	1.411 (2)	C13—C14	1.384 (3)
O5—H5	0.84	C13—H13	0.95
O6—C3	1.418 (2)	C14—C15	1.393 (4)
O6—H6	0.84	C14—H14	0.95
C1—C2	1.532 (2)	C15—C16	1.385 (3)
C2—C3	1.531 (3)	C15—H15	0.95
C2—H2	1.00	C16—H16	0.95
C3—C4	1.526 (3)	C17—C18	1.522 (3)
C3—H3A	1.00	C17—H17	1.00
N1—C17	1.510 (3)	C18—H18A	0.98
N1—H1A	0.91	C18—H18B	0.98
N1—H1B	0.91	C18—H18C	0.98
N1—H1C	0.91
C4—O3—H3	109.5	C16—C11—C17	119.55 (19)
C2—O5—H5	109.5	C13—C12—C11	120.6 (2)
C3—O6—H6	109.5	C13—C12—H12	119.7
O2—C1—O1	126.14 (17)	C11—C12—H12	119.7
O2—C1—C2	117.76 (16)	C14—C13—C12	120.3 (2)
O1—C1—C2	116.08 (16)	C14—C13—H13	119.8
O5—C2—C3	110.16 (15)	C12—C13—H13	119.8
O5—C2—C1	110.55 (14)	C13—C14—C15	119.5 (2)
C3—C2—C1	110.73 (15)	C13—C14—H14	120.2
O5—C2—H2	108.4	C15—C14—H14	120.2
C3—C2—H2	108.4	C16—C15—C14	120.0 (2)
C1—C2—H2	108.4	C16—C15—H15	120.0
O6—C3—C4	112.09 (16)	C14—C15—H15	120.0
O6—C3—C2	110.64 (15)	C15—C16—C11	120.9 (2)
C4—C3—C2	109.33 (16)	C15—C16—H16	119.6
O6—C3—H3A	108.2	C11—C16—H16	119.6
C4—C3—H3A	108.2	N1—C17—C11	110.37 (16)
C2—C3—H3A	108.2	N1—C17—C18	108.54 (17)
O4—C4—O3	125.20 (17)	C11—C17—C18	113.16 (17)
O4—C4—C3	121.87 (16)	N1—C17—H17	108.2
O3—C4—C3	112.91 (16)	C11—C17—H17	108.2
C17—N1—H1A	109.5	C18—C17—H17	108.2
C17—N1—H1B	109.5	C17—C18—H18A	109.5
H1A—N1—H1B	109.5	C17—C18—H18B	109.5
C17—N1—H1C	109.5	H18A—C18—H18B	109.5
H1A—N1—H1C	109.5	C17—C18—H18C	109.5
H1B—N1—H1C	109.5	H18A—C18—H18C	109.5
C12—C11—C16	118.7 (2)	H18B—C18—H18C	109.5
C12—C11—C17	121.78 (19)
O2—C1—C2—O5	−0.4 (3)	C16—C11—C12—C13	0.0 (3)
O1—C1—C2—O5	−178.99 (17)	C17—C11—C12—C13	−178.87 (19)
O2—C1—C2—C3	−122.78 (19)	C11—C12—C13—C14	0.4 (3)
O1—C1—C2—C3	58.6 (2)	C12—C13—C14—C15	−0.8 (3)
O5—C2—C3—O6	−65.99 (19)	C13—C14—C15—C16	1.0 (3)
C1—C2—C3—O6	56.61 (19)	C14—C15—C16—C11	−0.7 (3)
O5—C2—C3—C4	57.9 (2)	C12—C11—C16—C15	0.2 (3)
C1—C2—C3—C4	−179.47 (15)	C17—C11—C16—C15	179.1 (2)
O6—C3—C4—O4	−151.29 (18)	C12—C11—C17—N1	−65.4 (2)
C2—C3—C4—O4	85.7 (2)	C16—C11—C17—N1	115.74 (19)
O6—C3—C4—O3	30.1 (2)	C12—C11—C17—C18	56.4 (3)
C2—C3—C4—O3	−92.9 (2)	C16—C11—C17—C18	−122.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^i	0.84	1.65	2.486 (2)	174
O5—H5···O2	0.84	2.11	2.616 (2)	119
O5—H5···O4^ii	0.84	2.18	2.797 (2)	130
O6—H6···O3	0.84	2.17	2.652 (2)	116
N1—H1A···O1	0.91	2.00	2.901 (2)	172
N1—H1B···O5^iii	0.91	2.02	2.867 (2)	154
N1—H1C···O2^iv	0.91	1.93	2.842 (2)	177

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

(II) (S)-1-Phenylethylammonium rac-tartrate(1-)

Crystal data

C8H12N·C4H5O6	F(000) = 576
Mr = 271.27	Dx = 1.336 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3191 reflections
a = 7.3025 (2) Å	θ = 2.7–27.7°
b = 22.8901 (11) Å	µ = 0.11 mm^−1
c = 8.1193 (3) Å	T = 150 K
β = 96.599 (2)°	Needle, colourless
V = 1348.19 (9) Å^3	0.28 × 0.16 × 0.14 mm
Z = 4

Data collection

Kappa-CCD diffractometer	3191 independent reflections
Radiation source: fine-focus sealed X-ray tube	2734 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.129
ϕ scans, and ω scans with κ offsets	θmax = 27.7°, θmin = 2.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.584, Tmax = 0.998	k = −29→29
15852 measured reflections	l = −8→10

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)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.0775P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3191 reflections	Δρmax = 0.34 e Å^−3
354 parameters	Δρmin = −0.24 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (6)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O11	0.3272 (3)	0.58482 (10)	0.9097 (2)	0.0363 (5)
O12	0.3593 (3)	0.55621 (11)	1.1755 (3)	0.0405 (5)
O15	0.7170 (3)	0.54608 (10)	1.1988 (2)	0.0366 (5)
O16	0.6239 (3)	0.47743 (9)	0.9105 (3)	0.0370 (5)
O13	0.9965 (3)	0.48977 (10)	0.9489 (3)	0.0381 (5)
O14	0.9756 (3)	0.58685 (10)	0.9130 (3)	0.0376 (5)
C11	0.4206 (4)	0.56938 (13)	1.0442 (3)	0.0326 (6)
C12	0.6307 (4)	0.56948 (14)	1.0461 (3)	0.0325 (6)
C13	0.6947 (4)	0.53480 (14)	0.9027 (3)	0.0331 (6)
C14	0.9063 (4)	0.53409 (14)	0.9225 (3)	0.0327 (6)
O21	0.5816 (3)	0.41528 (10)	0.6188 (2)	0.0351 (4)
O22	0.5502 (3)	0.44629 (11)	0.3542 (3)	0.0404 (5)
O25	0.1910 (3)	0.45112 (10)	0.3258 (2)	0.0373 (5)
O26	0.2844 (3)	0.52255 (10)	0.6151 (3)	0.0372 (5)
O23	−0.0897 (3)	0.51062 (10)	0.5760 (3)	0.0385 (5)
O24	−0.0679 (3)	0.41304 (10)	0.6051 (3)	0.0380 (5)
C21	0.4876 (4)	0.43169 (13)	0.4833 (3)	0.0334 (6)
C22	0.2775 (4)	0.42982 (13)	0.4803 (3)	0.0328 (6)
C23	0.2117 (4)	0.46514 (14)	0.6218 (3)	0.0334 (6)
C24	0.0007 (4)	0.46629 (14)	0.5987 (3)	0.0343 (6)
N3	0.0680 (3)	0.58651 (11)	1.3443 (3)	0.0333 (5)
C31	0.1949 (4)	0.68531 (14)	1.4188 (4)	0.0384 (6)
C32	0.2889 (5)	0.67206 (15)	1.5730 (4)	0.0436 (7)
C33	0.4374 (5)	0.70634 (17)	1.6392 (5)	0.0505 (8)
C34	0.4901 (5)	0.75446 (17)	1.5522 (5)	0.0522 (9)
C35	0.3969 (5)	0.76803 (17)	1.3991 (5)	0.0543 (9)
C36	0.2503 (5)	0.73294 (16)	1.3315 (4)	0.0482 (8)
C37	0.0260 (4)	0.65053 (14)	1.3515 (4)	0.0388 (6)
C38	−0.1344 (5)	0.65949 (17)	1.4535 (5)	0.0520 (8)
N4	0.8388 (3)	0.41354 (11)	0.1841 (3)	0.0341 (5)
C41	0.9610 (4)	0.31838 (14)	0.0957 (4)	0.0371 (6)
C42	1.0452 (5)	0.34204 (15)	−0.0339 (4)	0.0424 (7)
C43	1.1758 (5)	0.31047 (16)	−0.1084 (4)	0.0468 (7)
C44	1.2232 (4)	0.25444 (15)	−0.0543 (4)	0.0449 (7)
C45	1.1391 (5)	0.23028 (16)	0.0749 (5)	0.0481 (8)
C46	1.0097 (5)	0.26189 (15)	0.1493 (4)	0.0447 (7)
C47	0.8086 (4)	0.34888 (13)	0.1724 (4)	0.0360 (6)
C48	0.6201 (4)	0.33761 (17)	0.0746 (4)	0.0468 (7)
H15	0.6358	0.5343	1.2562	0.055*
H16	0.6220	0.4614	0.8173	0.056*
H14	1.0907	0.5846	0.9157	0.056*
H15A	0.6722	0.6109	1.0369	0.039*
H16A	0.6470	0.5534	0.7947	0.040*
H25	0.2716	0.4636	0.2688	0.056*
H26	0.2899	0.5380	0.7094	0.056*
H24	−0.1818	0.4151	0.6112	0.057*
H25A	0.2395	0.3882	0.4926	0.039*
H26A	0.2568	0.4466	0.7305	0.040*
H3A	0.1576	0.5806	1.2770	0.050*
H3B	−0.0357	0.5668	1.3036	0.050*
H3C	0.1074	0.5733	1.4481	0.050*
H32	0.2518	0.6395	1.6336	0.052*
H33	0.5023	0.6967	1.7439	0.061*
H34	0.5902	0.7781	1.5978	0.063*
H35	0.4323	0.8012	1.3398	0.065*
H36	0.1885	0.7418	1.2250	0.058*
H37	−0.0137	0.6643	1.2360	0.047*
H38A	−0.0988	0.6461	1.5673	0.078*
H38B	−0.2412	0.6371	1.4042	0.078*
H38C	−0.1662	0.7011	1.4545	0.078*
H4A	0.7620	0.4293	0.2529	0.051*
H4B	0.9579	0.4209	0.2250	0.051*
H4C	0.8148	0.4298	0.0816	0.051*
H42	1.0131	0.3803	−0.0721	0.051*
H43	1.2327	0.3273	−0.1965	0.056*
H44	1.3124	0.2328	−0.1051	0.054*
H45	1.1706	0.1919	0.1122	0.058*
H46	0.9534	0.2450	0.2378	0.054*
H47	0.8062	0.3333	0.2872	0.043*
H48A	0.6179	0.3540	−0.0371	0.070*
H48B	0.5239	0.3562	0.1314	0.070*
H48C	0.5976	0.2954	0.0669	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0331 (10)	0.0418 (12)	0.0339 (10)	0.0007 (9)	0.0033 (8)	0.0017 (8)
O12	0.0357 (10)	0.0512 (13)	0.0359 (11)	0.0044 (10)	0.0097 (9)	0.0043 (9)
O15	0.0335 (10)	0.0484 (13)	0.0277 (9)	−0.0021 (9)	0.0026 (7)	0.0015 (9)
O16	0.0399 (10)	0.0381 (11)	0.0331 (10)	−0.0056 (9)	0.0041 (8)	−0.0042 (8)
O13	0.0392 (10)	0.0381 (12)	0.0372 (11)	0.0030 (9)	0.0058 (9)	0.0026 (9)
O14	0.0302 (9)	0.0380 (11)	0.0455 (12)	0.0007 (8)	0.0072 (8)	0.0010 (9)
C11	0.0301 (13)	0.0343 (14)	0.0339 (14)	−0.0012 (11)	0.0062 (11)	−0.0017 (11)
C12	0.0307 (13)	0.0371 (15)	0.0296 (13)	−0.0009 (11)	0.0037 (10)	0.0001 (11)
C13	0.0341 (14)	0.0346 (14)	0.0309 (13)	−0.0004 (12)	0.0048 (10)	0.0015 (11)
C14	0.0333 (13)	0.0362 (15)	0.0290 (13)	−0.0003 (12)	0.0061 (10)	0.0014 (11)
O21	0.0320 (9)	0.0398 (11)	0.0332 (10)	0.0021 (9)	0.0027 (7)	0.0014 (9)
O22	0.0350 (10)	0.0523 (14)	0.0345 (11)	0.0021 (9)	0.0074 (8)	0.0028 (9)
O25	0.0329 (10)	0.0497 (13)	0.0292 (10)	−0.0014 (9)	0.0027 (8)	0.0011 (9)
O26	0.0404 (11)	0.0390 (12)	0.0320 (10)	−0.0020 (9)	0.0032 (8)	−0.0037 (8)
O23	0.0359 (11)	0.0417 (12)	0.0383 (11)	0.0055 (9)	0.0064 (8)	0.0053 (9)
O24	0.0327 (9)	0.0403 (11)	0.0419 (11)	−0.0006 (9)	0.0079 (8)	0.0005 (9)
C21	0.0340 (13)	0.0338 (15)	0.0328 (13)	−0.0005 (11)	0.0056 (11)	−0.0020 (11)
C22	0.0327 (13)	0.0371 (15)	0.0287 (13)	0.0003 (12)	0.0034 (10)	0.0008 (11)
C23	0.0336 (13)	0.0353 (15)	0.0317 (14)	0.0011 (12)	0.0047 (10)	0.0010 (11)
C24	0.0345 (13)	0.0431 (17)	0.0255 (12)	0.0028 (13)	0.0047 (10)	0.0003 (11)
N3	0.0349 (11)	0.0340 (12)	0.0313 (12)	0.0002 (10)	0.0050 (9)	−0.0016 (9)
C31	0.0419 (15)	0.0354 (15)	0.0376 (15)	−0.0012 (13)	0.0033 (12)	−0.0001 (12)
C32	0.0501 (17)	0.0399 (16)	0.0393 (15)	−0.0043 (14)	−0.0008 (13)	−0.0006 (12)
C33	0.0502 (18)	0.0503 (19)	0.0479 (18)	−0.0006 (16)	−0.0071 (15)	−0.0070 (15)
C34	0.0442 (17)	0.0463 (19)	0.065 (2)	−0.0059 (15)	0.0036 (16)	−0.0136 (17)
C35	0.059 (2)	0.0423 (19)	0.062 (2)	−0.0085 (16)	0.0104 (17)	0.0048 (16)
C36	0.0549 (19)	0.0431 (17)	0.0455 (17)	−0.0015 (15)	0.0017 (14)	0.0058 (14)
C37	0.0411 (15)	0.0351 (15)	0.0394 (15)	0.0025 (13)	0.0002 (12)	−0.0002 (12)
C38	0.0434 (17)	0.052 (2)	0.061 (2)	0.0027 (15)	0.0078 (15)	−0.0162 (17)
N4	0.0330 (11)	0.0373 (13)	0.0322 (11)	−0.0003 (11)	0.0039 (9)	−0.0013 (10)
C41	0.0403 (15)	0.0388 (15)	0.0311 (13)	−0.0003 (13)	0.0000 (11)	0.0001 (11)
C42	0.0485 (17)	0.0374 (15)	0.0421 (15)	0.0039 (14)	0.0092 (13)	0.0028 (13)
C43	0.0508 (18)	0.0464 (18)	0.0438 (17)	0.0001 (15)	0.0079 (14)	−0.0027 (14)
C44	0.0377 (15)	0.0417 (16)	0.0543 (18)	0.0028 (13)	0.0014 (13)	−0.0115 (14)
C45	0.0452 (17)	0.0372 (16)	0.060 (2)	0.0023 (14)	−0.0021 (15)	−0.0020 (15)
C46	0.0492 (18)	0.0386 (17)	0.0452 (17)	−0.0003 (14)	0.0009 (14)	0.0053 (13)
C47	0.0380 (14)	0.0336 (15)	0.0362 (14)	−0.0025 (12)	0.0038 (11)	0.0025 (11)
C48	0.0384 (16)	0.0478 (19)	0.0536 (18)	−0.0045 (14)	0.0027 (13)	−0.0076 (15)

Geometric parameters (Å, º)

O11—C11	1.269 (4)	C32—C33	1.395 (5)
O12—C11	1.240 (3)	C32—H32	0.95
O15—C12	1.428 (3)	C33—C34	1.387 (6)
O15—H15	0.84	C33—H33	0.95
O16—C13	1.415 (4)	C34—C35	1.382 (6)
O16—H16	0.84	C34—H34	0.95
O13—C14	1.215 (4)	C35—C36	1.399 (5)
O14—C14	1.315 (4)	C35—H35	0.95
O14—H14	0.84	C36—H36	0.95
C11—C12	1.533 (4)	C37—C38	1.523 (5)
C12—C13	1.527 (4)	C37—H37	1.00
C12—H15A	1.00	C38—H38A	0.98
C13—C14	1.535 (4)	C38—H38B	0.98
C13—H16A	1.00	C38—H38C	0.98
O21—C21	1.284 (4)	N4—C47	1.498 (4)
O22—C21	1.237 (4)	N4—H4A	0.91
O25—C22	1.424 (3)	N4—H4B	0.91
O25—H25	0.84	N4—H4C	0.91
O26—C23	1.421 (4)	C41—C42	1.388 (4)
O26—H26	0.84	C41—C46	1.397 (5)
O23—C24	1.213 (4)	C41—C47	1.508 (4)
O24—C24	1.321 (4)	C42—C43	1.389 (5)
O24—H24	0.84	C42—H42	0.95
C21—C22	1.532 (4)	C43—C44	1.386 (5)
C22—C23	1.527 (4)	C43—H43	0.95
C22—H25A	1.00	C44—C45	1.390 (5)
C23—C24	1.531 (4)	C44—H44	0.95
C23—H26A	1.00	C45—C46	1.383 (5)
N3—C37	1.500 (4)	C45—H45	0.95
N3—H3A	0.91	C46—H46	0.95
N3—H3B	0.91	C47—C48	1.530 (4)
N3—H3C	0.91	C47—H47	1.00
C31—C36	1.386 (5)	C48—H48A	0.98
C31—C32	1.390 (4)	C48—H48B	0.98
C31—C37	1.516 (4)	C48—H48C	0.98
C12—O15—H15	109.5	C35—C34—C33	120.0 (3)
C13—O16—H16	109.5	C35—C34—H34	120.0
C14—O14—H14	109.5	C33—C34—H34	120.0
O12—C11—O11	126.6 (3)	C34—C35—C36	120.0 (3)
O12—C11—C12	116.8 (2)	C34—C35—H35	120.0
O11—C11—C12	116.5 (2)	C36—C35—H35	120.0
O15—C12—C13	108.9 (2)	C31—C36—C35	120.4 (3)
O15—C12—C11	110.5 (2)	C31—C36—H36	119.8
C13—C12—C11	112.7 (2)	C35—C36—H36	119.8
O15—C12—H15A	108.2	N3—C37—C31	111.5 (2)
C13—C12—H15A	108.2	N3—C37—C38	109.0 (3)
C11—C12—H15A	108.2	C31—C37—C38	112.2 (3)
O16—C13—C12	107.6 (2)	N3—C37—H37	108.0
O16—C13—C14	110.7 (2)	C31—C37—H37	108.0
C12—C13—C14	108.6 (2)	C38—C37—H37	108.0
O16—C13—H16A	110.0	C37—C38—H38A	109.5
C12—C13—H16A	110.0	C37—C38—H38B	109.5
C14—C13—H16A	110.0	H38A—C38—H38B	109.5
O13—C14—O14	124.9 (3)	C37—C38—H38C	109.5
O13—C14—C13	123.1 (3)	H38A—C38—H38C	109.5
O14—C14—C13	112.0 (2)	H38B—C38—H38C	109.5
C22—O25—H25	109.5	C47—N4—H4A	109.5
C23—O26—H26	109.5	C47—N4—H4B	109.5
C24—O24—H24	109.5	H4A—N4—H4B	109.5
O22—C21—O21	126.3 (3)	C47—N4—H4C	109.5
O22—C21—C22	117.5 (3)	H4A—N4—H4C	109.5
O21—C21—C22	116.2 (2)	H4B—N4—H4C	109.5
O25—C22—C23	109.6 (2)	C42—C41—C46	118.6 (3)
O25—C22—C21	110.3 (2)	C42—C41—C47	123.0 (3)
C23—C22—C21	112.0 (2)	C46—C41—C47	118.3 (3)
O25—C22—H25A	108.3	C41—C42—C43	120.9 (3)
C23—C22—H25A	108.3	C41—C42—H42	119.6
C21—C22—H25A	108.3	C43—C42—H42	119.6
O26—C23—C22	108.0 (2)	C44—C43—C42	120.1 (3)
O26—C23—C24	110.8 (2)	C44—C43—H43	119.9
C22—C23—C24	108.4 (2)	C42—C43—H43	119.9
O26—C23—H26A	109.9	C43—C44—C45	119.4 (3)
C22—C23—H26A	109.9	C43—C44—H44	120.3
C24—C23—H26A	109.9	C45—C44—H44	120.3
O23—C24—O24	125.2 (3)	C46—C45—C44	120.3 (3)
O23—C24—C23	123.7 (3)	C46—C45—H45	119.8
O24—C24—C23	111.1 (2)	C44—C45—H45	119.8
C37—N3—H3A	109.5	C45—C46—C41	120.7 (3)
C37—N3—H3B	109.5	C45—C46—H46	119.7
H3A—N3—H3B	109.5	C41—C46—H46	119.7
C37—N3—H3C	109.5	N4—C47—C41	111.9 (2)
H3A—N3—H3C	109.5	N4—C47—C48	108.5 (2)
H3B—N3—H3C	109.5	C41—C47—C48	111.7 (3)
C36—C31—C32	119.3 (3)	N4—C47—H47	108.2
C36—C31—C37	120.1 (3)	C41—C47—H47	108.2
C32—C31—C37	120.5 (3)	C48—C47—H47	108.2
C31—C32—C33	120.4 (3)	C47—C48—H48A	109.5
C31—C32—H32	119.8	C47—C48—H48B	109.5
C33—C32—H32	119.8	H48A—C48—H48B	109.5
C34—C33—C32	119.9 (3)	C47—C48—H48C	109.5
C34—C33—H33	120.0	H48A—C48—H48C	109.5
C32—C33—H33	120.0	H48B—C48—H48C	109.5
O12—C11—C12—O15	7.9 (4)	C36—C31—C32—C33	0.1 (5)
O11—C11—C12—O15	−174.6 (3)	C37—C31—C32—C33	−176.0 (3)
O12—C11—C12—C13	129.9 (3)	C31—C32—C33—C34	1.0 (6)
O11—C11—C12—C13	−52.5 (4)	C32—C33—C34—C35	−0.7 (6)
O15—C12—C13—O16	66.6 (3)	C33—C34—C35—C36	−0.5 (6)
C11—C12—C13—O16	−56.3 (3)	C32—C31—C36—C35	−1.3 (5)
O15—C12—C13—C14	−53.3 (3)	C37—C31—C36—C35	174.8 (3)
C11—C12—C13—C14	−176.2 (2)	C34—C35—C36—C31	1.5 (6)
O16—C13—C14—O13	−3.1 (4)	C36—C31—C37—N3	127.7 (3)
C12—C13—C14—O13	114.8 (3)	C32—C31—C37—N3	−56.3 (4)
O16—C13—C14—O14	179.0 (2)	C36—C31—C37—C38	−109.7 (4)
C12—C13—C14—O14	−63.1 (3)	C32—C31—C37—C38	66.3 (4)
O22—C21—C22—O25	−5.2 (4)	C46—C41—C42—C43	−0.3 (5)
O21—C21—C22—O25	177.8 (3)	C47—C41—C42—C43	−175.3 (3)
O22—C21—C22—C23	−127.5 (3)	C41—C42—C43—C44	0.3 (5)
O21—C21—C22—C23	55.5 (3)	C42—C43—C44—C45	0.0 (5)
O25—C22—C23—O26	−68.8 (3)	C43—C44—C45—C46	−0.2 (5)
C21—C22—C23—O26	54.0 (3)	C44—C45—C46—C41	0.2 (5)
O25—C22—C23—C24	51.3 (3)	C42—C41—C46—C45	0.0 (5)
C21—C22—C23—C24	174.1 (2)	C47—C41—C46—C45	175.3 (3)
O26—C23—C24—O23	0.8 (4)	C42—C41—C47—N4	−37.7 (4)
C22—C23—C24—O23	−117.6 (3)	C46—C41—C47—N4	147.3 (3)
O26—C23—C24—O24	−179.9 (2)	C42—C41—C47—C48	84.2 (4)
C22—C23—C24—O24	61.7 (3)	C46—C41—C47—C48	−90.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O15—H15···O12	0.84	2.11	2.607 (3)	118
O15—H15···O22^i	0.84	2.28	2.941 (3)	136
O16—H16···O21	0.84	1.92	2.750 (3)	169
O14—H14···O11^ii	0.84	1.73	2.571 (3)	175
O25—H25···O22	0.84	2.11	2.610 (3)	118
O25—H25···O12^iii	0.84	2.36	3.022 (3)	136
O26—H26···O11	0.84	1.94	2.771 (3)	170
O24—H24···O21^iv	0.84	1.74	2.576 (3)	177
N3—H3A···O12	0.91	1.85	2.749 (3)	167
N3—H3B···O15^iv	0.91	1.96	2.850 (3)	164
N3—H3C···O26^i	0.91	2.11	2.945 (3)	152
N3—H3C···O23^i	0.91	2.36	2.894 (3)	118
N4—H4A···O22	0.91	1.87	2.753 (3)	162
N4—H4B···O25^ii	0.91	1.93	2.828 (3)	169
N4—H4C···O16^iii	0.91	2.15	2.956 (3)	147
N4—H4C···O13^iii	0.91	2.27	2.919 (3)	128

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

(III) (R)-1-Phenylethylammonium (R,R)-tartrate(1-)

Crystal data

C8H12N·C4H5O6	F(000) = 576
Mr = 271.27	Dx = 1.339 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9403 reflections
a = 7.2952 (2) Å	θ = 2.7–27.5°
b = 22.8935 (11) Å	µ = 0.11 mm^−1
c = 8.1100 (3) Å	T = 150 K
β = 96.603 (2)°	Block, colourless
V = 1345.49 (9) Å^3	0.36 × 0.26 × 0.20 mm
Z = 4

Data collection

Kappa-CCD diffractometer	3160 independent reflections
Radiation source: fine-focus sealed X-ray tube	2446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.869, Tmax = 0.991	k = −27→29
9403 measured reflections	l = −9→10

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0449P)^2 + 0.0771P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3160 reflections	Δρmax = 0.18 e Å^−3
354 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O11	0.3272 (2)	0.41530 (9)	0.9097 (2)	0.0257 (5)
O12	0.3595 (2)	0.44399 (9)	1.1757 (2)	0.0288 (5)
O13	0.9959 (2)	0.51043 (9)	0.9486 (2)	0.0270 (5)
O14	0.9757 (2)	0.41304 (9)	0.9131 (3)	0.0271 (5)
H14	1.0908	0.4153	0.9147	0.041*
O15	0.7173 (2)	0.45378 (9)	1.1989 (2)	0.0252 (5)
H15	0.6373	0.4698	1.2505	0.038*
O16	0.6238 (3)	0.52254 (8)	0.9103 (2)	0.0253 (4)
H16	0.6153	0.5378	0.8156	0.038*
C11	0.4202 (3)	0.43080 (12)	1.0439 (3)	0.0212 (6)
C12	0.6310 (3)	0.43043 (13)	1.0460 (3)	0.0220 (6)
H12A	0.6724	0.3890	1.0365	0.026*
C13	0.6952 (3)	0.46536 (13)	0.9026 (3)	0.0207 (6)
H13A	0.6475	0.4468	0.7944	0.025*
C14	0.9061 (3)	0.46575 (13)	0.9224 (3)	0.0218 (6)
O21	0.5810 (2)	0.58454 (9)	0.6180 (2)	0.0248 (4)
O22	0.5501 (2)	0.55369 (9)	0.3546 (2)	0.0299 (5)
O23	−0.0889 (3)	0.48931 (9)	0.5760 (2)	0.0275 (5)
O24	−0.0681 (2)	0.58693 (9)	0.6050 (2)	0.0269 (5)
H24	−0.1826	0.5849	0.6083	0.040*
O25	0.1912 (2)	0.54904 (9)	0.3256 (2)	0.0267 (5)
H25	0.2717	0.5361	0.2690	0.040*
O26	0.2846 (3)	0.47761 (9)	0.6146 (2)	0.0258 (5)
H26	0.2974	0.4632	0.7104	0.039*
C21	0.4874 (3)	0.56854 (12)	0.4839 (3)	0.0223 (6)
C22	0.2775 (3)	0.56993 (13)	0.4797 (3)	0.0226 (6)
H22A	0.2390	0.6115	0.4922	0.027*
C23	0.2120 (3)	0.53486 (13)	0.6208 (3)	0.0220 (6)
H23A	0.2577	0.5534	0.7294	0.026*
C24	0.0006 (3)	0.53375 (13)	0.5993 (3)	0.0217 (6)
N3	0.0681 (3)	0.41331 (10)	1.3442 (3)	0.0231 (5)
H3A	0.1070	0.4266	1.4481	0.035*
H3B	−0.0357	0.4329	1.3029	0.035*
H3C	0.1582	0.4193	1.2772	0.035*
C31	0.1950 (4)	0.31489 (13)	1.4185 (4)	0.0260 (6)
C32	0.2900 (4)	0.32782 (14)	1.5730 (4)	0.0333 (7)
H32	0.2536	0.3604	1.6341	0.040*
C33	0.4377 (4)	0.29348 (15)	1.6387 (4)	0.0391 (8)
H33	0.5028	0.3030	1.7435	0.047*
C34	0.4897 (4)	0.24573 (15)	1.5519 (4)	0.0418 (8)
H34	0.5898	0.2220	1.5975	0.050*
C35	0.3967 (4)	0.23222 (16)	1.3988 (5)	0.0437 (8)
H35	0.4326	0.1992	1.3391	0.052*
C36	0.2505 (4)	0.26695 (14)	1.3321 (4)	0.0368 (7)
H36	0.1877	0.2578	1.2260	0.044*
C37	0.0268 (4)	0.34927 (13)	1.3516 (4)	0.0278 (7)
H37	−0.0127	0.3355	1.2359	0.033*
C38	−0.1340 (4)	0.34033 (16)	1.4533 (5)	0.0421 (8)
H38A	−0.1012	0.3557	1.5655	0.063*
H38B	−0.1614	0.2985	1.4595	0.063*
H38C	−0.2429	0.3610	1.4002	0.063*
N4	0.8388 (3)	0.58646 (10)	0.1844 (3)	0.0236 (5)
H4A	0.8162	0.5702	0.0817	0.035*
H4B	0.9578	0.5793	0.2263	0.035*
H4C	0.7614	0.5706	0.2526	0.035*
C41	0.9609 (4)	0.68175 (13)	0.0957 (3)	0.0265 (6)
C42	1.0442 (4)	0.65797 (14)	−0.0343 (4)	0.0320 (7)
H42	1.0115	0.6198	−0.0729	0.038*
C43	1.1751 (4)	0.68962 (14)	−0.1082 (4)	0.0361 (7)
H43	1.2324	0.6728	−0.1963	0.043*
C44	1.2225 (4)	0.74541 (14)	−0.0546 (4)	0.0358 (7)
H44	1.3118	0.7670	−0.1056	0.043*
C45	1.1386 (4)	0.76969 (14)	0.0745 (4)	0.0377 (8)
H45	1.1699	0.8082	0.1116	0.045*
C46	1.0098 (4)	0.73805 (14)	0.1490 (4)	0.0339 (7)
H46	0.9538	0.7549	0.2379	0.041*
C47	0.8077 (4)	0.65096 (12)	0.1724 (4)	0.0251 (6)
H47	0.8050	0.6666	0.2872	0.030*
C48	0.6202 (4)	0.66221 (15)	0.0749 (4)	0.0385 (8)
H48A	0.6197	0.6472	−0.0383	0.058*
H48B	0.5956	0.7043	0.0710	0.058*
H48C	0.5243	0.6424	0.1292	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0198 (9)	0.0312 (12)	0.0260 (11)	−0.0019 (8)	0.0028 (8)	−0.0015 (9)
O12	0.0220 (9)	0.0377 (13)	0.0277 (11)	−0.0034 (9)	0.0069 (9)	−0.0032 (9)
O13	0.0250 (10)	0.0287 (12)	0.0279 (11)	−0.0042 (9)	0.0060 (9)	−0.0041 (9)
O14	0.0161 (8)	0.0259 (11)	0.0400 (12)	−0.0009 (8)	0.0057 (8)	−0.0003 (9)
O15	0.0176 (9)	0.0360 (13)	0.0218 (10)	0.0031 (8)	0.0011 (8)	0.0001 (9)
O16	0.0267 (10)	0.0280 (11)	0.0208 (10)	0.0042 (8)	0.0022 (8)	0.0027 (8)
C11	0.0184 (12)	0.0225 (15)	0.0228 (15)	0.0003 (11)	0.0030 (11)	0.0024 (12)
C12	0.0164 (12)	0.0261 (16)	0.0232 (14)	0.0020 (11)	0.0014 (11)	−0.0015 (12)
C13	0.0185 (12)	0.0224 (15)	0.0212 (14)	0.0007 (11)	0.0026 (11)	−0.0010 (11)
C14	0.0239 (14)	0.0246 (16)	0.0175 (13)	−0.0018 (13)	0.0049 (11)	−0.0016 (12)
O21	0.0199 (9)	0.0272 (11)	0.0271 (10)	−0.0015 (8)	0.0010 (8)	−0.0016 (9)
O22	0.0210 (10)	0.0406 (13)	0.0290 (11)	−0.0026 (9)	0.0066 (8)	−0.0010 (9)
O23	0.0234 (10)	0.0291 (12)	0.0304 (11)	−0.0054 (8)	0.0046 (8)	−0.0056 (9)
O24	0.0175 (9)	0.0287 (12)	0.0349 (11)	−0.0009 (9)	0.0050 (8)	−0.0017 (9)
O25	0.0202 (9)	0.0386 (13)	0.0210 (10)	0.0008 (9)	0.0012 (8)	−0.0001 (9)
O26	0.0258 (10)	0.0263 (12)	0.0251 (10)	0.0022 (8)	0.0017 (8)	0.0039 (8)
C21	0.0201 (13)	0.0215 (16)	0.0251 (15)	−0.0010 (11)	0.0015 (12)	0.0044 (12)
C22	0.0191 (12)	0.0265 (16)	0.0223 (14)	−0.0009 (12)	0.0028 (11)	−0.0004 (12)
C23	0.0204 (13)	0.0230 (15)	0.0224 (14)	0.0001 (11)	0.0019 (11)	−0.0001 (12)
C24	0.0200 (13)	0.0282 (17)	0.0175 (13)	−0.0009 (12)	0.0048 (11)	0.0007 (12)
N3	0.0214 (11)	0.0263 (13)	0.0212 (12)	−0.0002 (10)	0.0015 (9)	0.0023 (10)
C31	0.0246 (13)	0.0241 (16)	0.0293 (15)	−0.0010 (12)	0.0026 (12)	0.0018 (12)
C32	0.0345 (15)	0.0318 (18)	0.0326 (17)	0.0030 (13)	−0.0008 (13)	−0.0028 (13)
C33	0.0381 (17)	0.036 (2)	0.0412 (18)	−0.0017 (15)	−0.0048 (15)	0.0066 (16)
C34	0.0304 (16)	0.036 (2)	0.058 (2)	0.0059 (14)	0.0029 (16)	0.0144 (17)
C35	0.0435 (19)	0.0331 (19)	0.056 (2)	0.0064 (15)	0.0107 (17)	−0.0014 (16)
C36	0.0414 (18)	0.0315 (18)	0.0365 (17)	−0.0011 (14)	0.0006 (14)	−0.0038 (14)
C37	0.0258 (14)	0.0254 (16)	0.0314 (16)	−0.0059 (13)	−0.0003 (12)	−0.0002 (13)
C38	0.0283 (15)	0.041 (2)	0.057 (2)	0.0001 (14)	0.0082 (15)	0.0193 (17)
N4	0.0211 (11)	0.0274 (14)	0.0224 (12)	0.0001 (10)	0.0034 (9)	0.0006 (10)
C41	0.0246 (14)	0.0259 (16)	0.0279 (15)	0.0014 (12)	−0.0022 (12)	0.0008 (12)
C42	0.0354 (16)	0.0258 (16)	0.0350 (16)	−0.0032 (13)	0.0051 (13)	−0.0009 (13)
C43	0.0375 (17)	0.0327 (19)	0.0390 (18)	0.0010 (14)	0.0086 (14)	0.0036 (14)
C44	0.0261 (15)	0.0317 (18)	0.0485 (19)	−0.0008 (13)	−0.0011 (14)	0.0130 (16)
C45	0.0328 (16)	0.0239 (17)	0.054 (2)	−0.0011 (13)	−0.0055 (15)	0.0020 (15)
C46	0.0327 (16)	0.0289 (18)	0.0387 (17)	0.0021 (13)	−0.0019 (14)	−0.0044 (14)
C47	0.0246 (14)	0.0226 (15)	0.0279 (15)	0.0035 (12)	0.0017 (12)	−0.0032 (12)
C48	0.0285 (15)	0.0363 (19)	0.050 (2)	0.0070 (14)	0.0024 (14)	0.0063 (16)

Geometric parameters (Å, º)

O11—C11	1.265 (3)	C32—C33	1.389 (4)
O12—C11	1.241 (3)	C32—H32	0.95
O13—C14	1.220 (3)	C33—C34	1.377 (5)
O14—C14	1.315 (4)	C33—H33	0.95
O14—H14	0.84	C34—C35	1.380 (5)
O15—C12	1.428 (3)	C34—H34	0.95
O15—H15	0.84	C35—C36	1.389 (5)
O16—C13	1.413 (3)	C35—H35	0.95
O16—H16	0.84	C36—H36	0.95
C11—C12	1.536 (3)	C37—C38	1.523 (4)
C12—C13	1.529 (4)	C37—H37	1.00
C12—H12A	1.00	C38—H38A	0.98
C13—C14	1.529 (3)	C38—H38B	0.98
C13—H13A	1.00	C38—H38C	0.98
O21—C21	1.270 (3)	N4—C47	1.495 (4)
O22—C21	1.239 (3)	N4—H4A	0.91
O23—C24	1.212 (3)	N4—H4B	0.91
O24—C24	1.319 (3)	N4—H4C	0.91
O24—H24	0.84	C41—C42	1.387 (4)
O25—C22	1.416 (3)	C41—C46	1.393 (4)
O25—H25	0.84	C41—C47	1.514 (4)
O26—C23	1.417 (3)	C42—C43	1.389 (4)
O26—H26	0.84	C42—H42	0.95
C21—C22	1.528 (4)	C43—C44	1.381 (5)
C22—C23	1.519 (4)	C43—H43	0.95
C22—H22A	1.00	C44—C45	1.388 (5)
C23—C24	1.532 (3)	C44—H44	0.95
C23—H23A	1.00	C45—C46	1.380 (4)
N3—C37	1.499 (4)	C45—H45	0.95
N3—H3A	0.91	C46—H46	0.95
N3—H3B	0.91	C47—C48	1.521 (4)
N3—H3C	0.91	C47—H47	1.00
C31—C36	1.387 (4)	C48—H48A	0.98
C31—C32	1.392 (4)	C48—H48B	0.98
C31—C37	1.506 (4)	C48—H48C	0.98
C14—O14—H14	109.5	C33—C34—C35	120.1 (3)
C12—O15—H15	109.5	C33—C34—H34	119.9
C13—O16—H16	109.5	C35—C34—H34	119.9
O12—C11—O11	126.9 (2)	C34—C35—C36	119.9 (3)
O12—C11—C12	116.6 (2)	C34—C35—H35	120.1
O11—C11—C12	116.5 (2)	C36—C35—H35	120.1
O15—C12—C13	108.8 (2)	C31—C36—C35	120.7 (3)
O15—C12—C11	110.4 (2)	C31—C36—H36	119.6
C13—C12—C11	112.5 (2)	C35—C36—H36	119.6
O15—C12—H12A	108.4	N3—C37—C31	111.5 (2)
C13—C12—H12A	108.4	N3—C37—C38	108.9 (2)
C11—C12—H12A	108.4	C31—C37—C38	112.4 (2)
O16—C13—C14	111.2 (2)	N3—C37—H37	108.0
O16—C13—C12	107.7 (2)	C31—C37—H37	108.0
C14—C13—C12	108.4 (2)	C38—C37—H37	108.0
O16—C13—H13A	109.8	C37—C38—H38A	109.5
C14—C13—H13A	109.8	C37—C38—H38B	109.5
C12—C13—H13A	109.8	H38A—C38—H38B	109.5
O13—C14—O14	125.2 (2)	C37—C38—H38C	109.5
O13—C14—C13	122.5 (3)	H38A—C38—H38C	109.5
O14—C14—C13	112.3 (2)	H38B—C38—H38C	109.5
C24—O24—H24	109.5	C47—N4—H4A	109.5
C22—O25—H25	109.5	C47—N4—H4B	109.5
C23—O26—H26	109.5	H4A—N4—H4B	109.5
O22—C21—O21	126.1 (2)	C47—N4—H4C	109.5
O22—C21—C22	117.0 (2)	H4A—N4—H4C	109.5
O21—C21—C22	116.9 (2)	H4B—N4—H4C	109.5
O25—C22—C23	109.9 (2)	C42—C41—C46	118.7 (3)
O25—C22—C21	110.8 (2)	C42—C41—C47	122.5 (3)
C23—C22—C21	111.9 (2)	C46—C41—C47	118.6 (3)
O25—C22—H22A	108.0	C41—C42—C43	120.4 (3)
C23—C22—H22A	108.0	C41—C42—H42	119.8
C21—C22—H22A	108.0	C43—C42—H42	119.8
O26—C23—C22	108.1 (2)	C44—C43—C42	120.4 (3)
O26—C23—C24	110.9 (2)	C44—C43—H43	119.8
C22—C23—C24	108.8 (2)	C42—C43—H43	119.8
O26—C23—H23A	109.7	C43—C44—C45	119.5 (3)
C22—C23—H23A	109.7	C43—C44—H44	120.3
C24—C23—H23A	109.7	C45—C44—H44	120.3
O23—C24—O24	125.4 (2)	C46—C45—C44	120.1 (3)
O23—C24—C23	123.3 (3)	C46—C45—H45	119.9
O24—C24—C23	111.2 (2)	C44—C45—H45	119.9
C37—N3—H3A	109.5	C45—C46—C41	120.9 (3)
C37—N3—H3B	109.5	C45—C46—H46	119.6
H3A—N3—H3B	109.5	C41—C46—H46	119.6
C37—N3—H3C	109.5	N4—C47—C41	111.9 (2)
H3A—N3—H3C	109.5	N4—C47—C48	108.8 (2)
H3B—N3—H3C	109.5	C41—C47—C48	111.7 (2)
C36—C31—C32	118.6 (3)	N4—C47—H47	108.1
C36—C31—C37	120.3 (3)	C41—C47—H47	108.1
C32—C31—C37	120.9 (3)	C48—C47—H47	108.1
C33—C32—C31	120.6 (3)	C47—C48—H48A	109.5
C33—C32—H32	119.7	C47—C48—H48B	109.5
C31—C32—H32	119.7	H48A—C48—H48B	109.5
C34—C33—C32	120.0 (3)	C47—C48—H48C	109.5
C34—C33—H33	120.0	H48A—C48—H48C	109.5
C32—C33—H33	120.0	H48B—C48—H48C	109.5
O12—C11—C12—O15	−8.0 (3)	C36—C31—C32—C33	0.2 (5)
O11—C11—C12—O15	174.8 (2)	C37—C31—C32—C33	175.7 (3)
O12—C11—C12—C13	−129.7 (3)	C31—C32—C33—C34	−0.9 (5)
O11—C11—C12—C13	53.1 (3)	C32—C33—C34—C35	0.7 (5)
O15—C12—C13—O16	−66.8 (2)	C33—C34—C35—C36	0.1 (5)
C11—C12—C13—O16	55.8 (3)	C32—C31—C36—C35	0.6 (5)
O15—C12—C13—C14	53.6 (3)	C37—C31—C36—C35	−174.9 (3)
C11—C12—C13—C14	176.2 (2)	C34—C35—C36—C31	−0.8 (5)
O16—C13—C14—O13	2.9 (4)	C36—C31—C37—N3	−128.2 (3)
C12—C13—C14—O13	−115.3 (3)	C32—C31—C37—N3	56.4 (4)
O16—C13—C14—O14	−179.0 (2)	C36—C31—C37—C38	109.2 (3)
C12—C13—C14—O14	62.8 (3)	C32—C31—C37—C38	−66.2 (4)
O22—C21—C22—O25	4.4 (3)	C46—C41—C42—C43	0.6 (4)
O21—C21—C22—O25	−177.8 (2)	C47—C41—C42—C43	175.5 (3)
O22—C21—C22—C23	127.4 (3)	C41—C42—C43—C44	−0.7 (4)
O21—C21—C22—C23	−54.8 (3)	C42—C43—C44—C45	0.2 (4)
O25—C22—C23—O26	69.1 (3)	C43—C44—C45—C46	0.4 (4)
C21—C22—C23—O26	−54.5 (3)	C44—C45—C46—C41	−0.5 (4)
O25—C22—C23—C24	−51.4 (3)	C42—C41—C46—C45	0.0 (4)
C21—C22—C23—C24	−175.0 (2)	C47—C41—C46—C45	−175.1 (3)
O26—C23—C24—O23	−1.7 (4)	C42—C41—C47—N4	38.1 (4)
C22—C23—C24—O23	117.1 (3)	C46—C41—C47—N4	−147.0 (3)
O26—C23—C24—O24	180.0 (2)	C42—C41—C47—C48	−84.1 (3)
C22—C23—C24—O24	−61.2 (3)	C46—C41—C47—C48	90.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O15—H15···O12	0.84	2.13	2.605 (2)	116
O15—H15···O22^i	0.84	2.22	2.944 (3)	144
O16—H16···O21	0.84	1.92	2.750 (3)	170
O14—H14···O11^ii	0.84	1.73	2.568 (2)	176
O25—H25···O22	0.84	2.11	2.604 (2)	117
O25—H25···O12^iii	0.84	2.35	3.019 (3)	136
O26—H26···O11	0.84	1.94	2.773 (3)	169
O24—H24···O21^iv	0.84	1.74	2.575 (2)	177
N3—H3A···O26^i	0.91	2.11	2.945 (3)	152
N3—H3A···O23^i	0.91	2.35	2.893 (3)	118
N3—H3B···O15^iv	0.91	1.96	2.847 (3)	165
N3—H3C···O12	0.91	1.85	2.747 (3)	167
N4—H4A···O16^iii	0.91	2.15	2.956 (3)	147
N4—H4A···O13^iii	0.91	2.25	2.916 (3)	129
N4—H4B···O25^ii	0.91	1.93	2.824 (3)	169
N4—H4C···O22	0.91	1.87	2.752 (3)	162
C36—H36···Cg^v	0.95	2.87	3.775 (3)	160

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

(IV) bis-(S)-1-Phenylethylammonium (R,R)-tartrate(2-)

Crystal data

2(C8H12N)·C4H4O6	F(000) = 420
Mr = 392.44	Dx = 1.267 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2434 reflections
a = 5.5620 (2) Å	θ = 3.1–27.5°
b = 16.0630 (3) Å	µ = 0.09 mm^−1
c = 11.8260 (4) Å	T = 150 K
β = 103.2810 (12)°	Plate, colourless
V = 1028.31 (5) Å^3	0.36 × 0.26 × 0.10 mm
Z = 2

Data collection

Kappa-CCD diffractometer	2434 independent reflections
Radiation source: fine-focus sealed X-ray tube	2187 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.877, Tmax = 0.995	k = −20→19
8194 measured reflections	l = −14→15

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)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 0.0872P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2434 reflections	Δρmax = 0.22 e Å^−3
260 parameters	Δρmin = −0.24 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (7)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.1580 (3)	0.78816 (10)	0.44636 (15)	0.0356 (4)
O2	0.1833 (3)	0.85005 (10)	0.54792 (15)	0.0368 (4)
O3	0.4876 (3)	0.60682 (11)	0.29174 (16)	0.0419 (4)
O4	0.2168 (3)	0.54276 (9)	0.37515 (14)	0.0324 (4)
O5	0.4621 (3)	0.71189 (10)	0.54093 (13)	0.0294 (3)
O6	0.3040 (3)	0.75508 (10)	0.30065 (13)	0.0314 (4)
C1	0.0678 (4)	0.78956 (13)	0.49291 (18)	0.0261 (4)
C2	0.2123 (4)	0.70972 (12)	0.48037 (17)	0.0224 (4)
C3	0.1882 (4)	0.69053 (13)	0.35161 (18)	0.0246 (4)
C4	0.3079 (4)	0.60629 (13)	0.33763 (17)	0.0263 (4)
N1	0.4500 (3)	0.42380 (10)	0.53992 (14)	0.0237 (4)
C11	0.4643 (4)	0.49557 (13)	0.72661 (17)	0.0244 (4)
C12	0.4416 (4)	0.58029 (14)	0.74569 (18)	0.0276 (4)
C13	0.3044 (4)	0.60863 (15)	0.8228 (2)	0.0326 (5)
C14	0.1926 (4)	0.55224 (16)	0.8827 (2)	0.0369 (5)
C15	0.2132 (4)	0.46768 (17)	0.8641 (2)	0.0368 (5)
C16	0.3480 (4)	0.43945 (14)	0.78661 (19)	0.0304 (5)
C17	0.6180 (3)	0.46243 (13)	0.64525 (17)	0.0245 (4)
C18	0.7785 (4)	0.52599 (14)	0.60186 (19)	0.0273 (4)
N2	−0.2307 (3)	0.47010 (11)	0.27975 (14)	0.0252 (4)
C21	−0.1154 (4)	0.37692 (12)	0.13222 (18)	0.0245 (4)
C22	0.1016 (4)	0.35321 (15)	0.2096 (2)	0.0321 (5)
C23	0.2448 (4)	0.28855 (16)	0.1819 (2)	0.0368 (5)
C24	0.1730 (4)	0.24790 (15)	0.0766 (2)	0.0348 (5)
C25	−0.0427 (5)	0.27039 (15)	−0.0009 (2)	0.0384 (6)
C26	−0.1873 (4)	0.33410 (14)	0.02711 (19)	0.0329 (5)
C27	−0.2724 (4)	0.44953 (13)	0.15384 (17)	0.0252 (4)
C28	−0.2211 (5)	0.52813 (14)	0.09017 (19)	0.0329 (5)
H5	0.5448	0.7384	0.5018	0.044*
H6	0.4363	0.7371	0.2869	0.047*
H2	0.1319	0.6630	0.5137	0.027*
H3	0.0090	0.6882	0.3118	0.030*
H1A	0.5424	0.3961	0.4977	0.036*
H1B	0.3612	0.4645	0.4954	0.036*
H1C	0.3452	0.3875	0.5631	0.036*
H12	0.5204	0.6193	0.7057	0.033*
H13	0.2877	0.6667	0.8343	0.039*
H14	0.1018	0.5715	0.9365	0.044*
H15	0.1348	0.4289	0.9046	0.044*
H16	0.3613	0.3814	0.7743	0.036*
H17	0.7285	0.4177	0.6872	0.029*
H18A	0.6733	0.5690	0.5567	0.041*
H18B	0.8736	0.4982	0.5526	0.041*
H18C	0.8921	0.5518	0.6683	0.041*
H2A	−0.0786	0.4934	0.3046	0.038*
H2B	−0.2401	0.4228	0.3208	0.038*
H2C	−0.3482	0.5067	0.2907	0.038*
H22	0.1526	0.3813	0.2819	0.039*
H23	0.3921	0.2724	0.2355	0.044*
H24	0.2723	0.2044	0.0575	0.042*
H25	−0.0921	0.2423	−0.0732	0.046*
H26	−0.3370	0.3488	−0.0259	0.039*
H27	−0.4501	0.4342	0.1246	0.030*
H28A	−0.0467	0.5436	0.1168	0.049*
H28B	−0.3251	0.5737	0.1066	0.049*
H28C	−0.2584	0.5175	0.0063	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0277 (8)	0.0282 (8)	0.0539 (10)	0.0071 (6)	0.0155 (7)	0.0018 (7)
O2	0.0546 (10)	0.0226 (8)	0.0398 (9)	−0.0097 (7)	0.0243 (8)	−0.0103 (6)
O3	0.0505 (10)	0.0331 (9)	0.0487 (10)	0.0117 (8)	0.0246 (9)	−0.0019 (7)
O4	0.0382 (8)	0.0197 (7)	0.0343 (8)	0.0006 (6)	−0.0020 (7)	−0.0007 (6)
O5	0.0259 (8)	0.0352 (9)	0.0255 (7)	−0.0007 (6)	0.0028 (6)	0.0018 (6)
O6	0.0434 (9)	0.0241 (8)	0.0291 (8)	0.0046 (6)	0.0130 (7)	0.0048 (6)
C1	0.0341 (11)	0.0198 (9)	0.0301 (10)	0.0007 (8)	0.0193 (9)	−0.0002 (8)
C2	0.0238 (10)	0.0201 (9)	0.0238 (9)	0.0000 (7)	0.0066 (7)	−0.0008 (7)
C3	0.0273 (10)	0.0210 (10)	0.0244 (9)	0.0030 (7)	0.0037 (8)	−0.0015 (7)
C4	0.0299 (10)	0.0231 (10)	0.0230 (10)	0.0051 (8)	0.0002 (8)	−0.0027 (8)
N1	0.0261 (8)	0.0206 (8)	0.0246 (8)	−0.0021 (6)	0.0060 (7)	−0.0006 (7)
C11	0.0233 (10)	0.0269 (10)	0.0217 (9)	−0.0011 (7)	0.0022 (8)	0.0029 (7)
C12	0.0290 (10)	0.0267 (11)	0.0265 (10)	−0.0020 (8)	0.0054 (8)	−0.0010 (8)
C13	0.0333 (11)	0.0316 (11)	0.0330 (11)	−0.0031 (9)	0.0080 (9)	−0.0068 (9)
C14	0.0365 (12)	0.0489 (15)	0.0275 (11)	−0.0020 (10)	0.0119 (9)	−0.0031 (10)
C15	0.0371 (12)	0.0452 (14)	0.0296 (11)	−0.0065 (10)	0.0109 (9)	0.0098 (10)
C16	0.0325 (11)	0.0273 (11)	0.0294 (10)	−0.0022 (8)	0.0033 (9)	0.0069 (8)
C17	0.0227 (9)	0.0227 (10)	0.0268 (10)	−0.0006 (7)	0.0033 (8)	0.0009 (8)
C18	0.0236 (9)	0.0271 (11)	0.0312 (10)	−0.0030 (8)	0.0061 (8)	−0.0008 (8)
N2	0.0303 (9)	0.0231 (9)	0.0238 (8)	0.0029 (7)	0.0097 (7)	0.0020 (7)
C21	0.0278 (10)	0.0239 (10)	0.0222 (9)	0.0004 (8)	0.0065 (8)	0.0017 (7)
C22	0.0333 (12)	0.0320 (11)	0.0284 (11)	0.0042 (9)	0.0017 (9)	−0.0065 (9)
C23	0.0351 (12)	0.0332 (12)	0.0394 (12)	0.0083 (10)	0.0030 (10)	−0.0036 (10)
C24	0.0418 (13)	0.0269 (11)	0.0369 (12)	0.0066 (9)	0.0113 (10)	−0.0047 (9)
C25	0.0522 (14)	0.0350 (14)	0.0272 (11)	0.0040 (10)	0.0076 (10)	−0.0068 (9)
C26	0.0383 (12)	0.0330 (12)	0.0244 (10)	0.0048 (9)	0.0013 (9)	−0.0005 (9)
C27	0.0281 (10)	0.0241 (10)	0.0236 (10)	0.0015 (7)	0.0064 (8)	0.0009 (8)
C28	0.0441 (12)	0.0278 (11)	0.0281 (11)	0.0058 (9)	0.0112 (9)	0.0074 (8)

Geometric parameters (Å, º)

O1—C1	1.250 (3)	C16—H16	0.95
O2—C1	1.260 (3)	C17—C18	1.521 (3)
O3—C4	1.242 (3)	C17—H17	1.00
O4—C4	1.264 (3)	C18—H18A	0.98
O5—C2	1.409 (2)	C18—H18B	0.98
O5—H5	0.84	C18—H18C	0.98
O6—C3	1.426 (3)	N2—C27	1.491 (3)
O6—H6	0.84	N2—H2A	0.91
C1—C2	1.539 (3)	N2—H2B	0.91
C2—C3	1.529 (3)	N2—H2C	0.91
C2—H2	1.00	C21—C22	1.390 (3)
C3—C4	1.534 (3)	C21—C26	1.396 (3)
C3—H3	1.00	C21—C27	1.514 (3)
N1—C17	1.508 (2)	C22—C23	1.393 (3)
N1—H1A	0.91	C22—H22	0.95
N1—H1B	0.91	C23—C24	1.381 (3)
N1—H1C	0.91	C23—H23	0.95
C11—C12	1.390 (3)	C24—C25	1.380 (4)
C11—C16	1.395 (3)	C24—H24	0.95
C11—C17	1.522 (3)	C25—C26	1.388 (3)
C12—C13	1.394 (3)	C25—H25	0.95
C12—H12	0.95	C26—H26	0.95
C13—C14	1.382 (3)	C27—C28	1.530 (3)
C13—H13	0.95	C27—H27	1.00
C14—C15	1.385 (4)	C28—H28A	0.98
C14—H14	0.95	C28—H28B	0.98
C15—C16	1.387 (3)	C28—H28C	0.98
C15—H15	0.95
C2—O5—H5	109.5	C18—C17—C11	115.91 (17)
C3—O6—H6	109.5	N1—C17—H17	107.9
O1—C1—O2	125.6 (2)	C18—C17—H17	107.9
O1—C1—C2	115.90 (18)	C11—C17—H17	107.9
O2—C1—C2	118.46 (19)	C17—C18—H18A	109.5
O5—C2—C3	111.23 (16)	C17—C18—H18B	109.5
O5—C2—C1	113.96 (17)	H18A—C18—H18B	109.5
C3—C2—C1	109.61 (16)	C17—C18—H18C	109.5
O5—C2—H2	107.2	H18A—C18—H18C	109.5
C3—C2—H2	107.2	H18B—C18—H18C	109.5
C1—C2—H2	107.2	C27—N2—H2A	109.5
O6—C3—C2	109.24 (16)	C27—N2—H2B	109.5
O6—C3—C4	110.27 (17)	H2A—N2—H2B	109.5
C2—C3—C4	110.13 (16)	C27—N2—H2C	109.5
O6—C3—H3	109.1	H2A—N2—H2C	109.5
C2—C3—H3	109.1	H2B—N2—H2C	109.5
C4—C3—H3	109.1	C22—C21—C26	118.62 (19)
O3—C4—O4	125.9 (2)	C22—C21—C27	123.18 (18)
O3—C4—C3	117.0 (2)	C26—C21—C27	118.14 (18)
O4—C4—C3	117.09 (18)	C21—C22—C23	120.4 (2)
C17—N1—H1A	109.5	C21—C22—H22	119.8
C17—N1—H1B	109.5	C23—C22—H22	119.8
H1A—N1—H1B	109.5	C24—C23—C22	120.2 (2)
C17—N1—H1C	109.5	C24—C23—H23	119.9
H1A—N1—H1C	109.5	C22—C23—H23	119.9
H1B—N1—H1C	109.5	C25—C24—C23	120.1 (2)
C12—C11—C16	118.7 (2)	C25—C24—H24	119.9
C12—C11—C17	122.01 (18)	C23—C24—H24	119.9
C16—C11—C17	119.27 (19)	C24—C25—C26	119.8 (2)
C11—C12—C13	120.7 (2)	C24—C25—H25	120.1
C11—C12—H12	119.7	C26—C25—H25	120.1
C13—C12—H12	119.7	C25—C26—C21	120.8 (2)
C14—C13—C12	120.0 (2)	C25—C26—H26	119.6
C14—C13—H13	120.0	C21—C26—H26	119.6
C12—C13—H13	120.0	N2—C27—C21	112.10 (16)
C13—C14—C15	119.9 (2)	N2—C27—C28	107.75 (17)
C13—C14—H14	120.1	C21—C27—C28	111.86 (17)
C15—C14—H14	120.1	N2—C27—H27	108.3
C14—C15—C16	120.2 (2)	C21—C27—H27	108.3
C14—C15—H15	119.9	C28—C27—H27	108.3
C16—C15—H15	119.9	C27—C28—H28A	109.5
C15—C16—C11	120.6 (2)	C27—C28—H28B	109.5
C15—C16—H16	119.7	H28A—C28—H28B	109.5
C11—C16—H16	119.7	C27—C28—H28C	109.5
N1—C17—C18	107.32 (16)	H28A—C28—H28C	109.5
N1—C17—C11	109.56 (15)	H28B—C28—H28C	109.5
O1—C1—C2—O5	−175.79 (18)	C12—C11—C16—C15	−0.3 (3)
O2—C1—C2—O5	4.3 (3)	C17—C11—C16—C15	177.96 (19)
O1—C1—C2—C3	58.8 (2)	C12—C11—C17—N1	−111.8 (2)
O2—C1—C2—C3	−121.1 (2)	C16—C11—C17—N1	70.0 (2)
O5—C2—C3—O6	−62.2 (2)	C12—C11—C17—C18	9.7 (3)
C1—C2—C3—O6	64.8 (2)	C16—C11—C17—C18	−168.40 (18)
O5—C2—C3—C4	59.1 (2)	C26—C21—C22—C23	0.6 (3)
C1—C2—C3—C4	−173.98 (16)	C27—C21—C22—C23	−176.6 (2)
O6—C3—C4—O3	3.5 (3)	C21—C22—C23—C24	0.5 (4)
C2—C3—C4—O3	−117.2 (2)	C22—C23—C24—C25	−0.9 (4)
O6—C3—C4—O4	−177.40 (17)	C23—C24—C25—C26	0.1 (4)
C2—C3—C4—O4	62.0 (2)	C24—C25—C26—C21	1.0 (4)
C16—C11—C12—C13	−0.3 (3)	C22—C21—C26—C25	−1.4 (3)
C17—C11—C12—C13	−178.45 (19)	C27—C21—C26—C25	175.9 (2)
C11—C12—C13—C14	1.1 (3)	C22—C21—C27—N2	−22.7 (3)
C12—C13—C14—C15	−1.3 (4)	C26—C21—C27—N2	160.08 (19)
C13—C14—C15—C16	0.7 (4)	C22—C21—C27—C28	98.5 (2)
C14—C15—C16—C11	0.0 (3)	C26—C21—C27—C28	−78.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1^i	0.84	2.07	2.882 (2)	161
O5—H5···O6	0.84	2.46	2.860 (2)	110
O6—H6···O3	0.84	2.11	2.603 (2)	117
N1—H1A···O2^ii	0.91	1.88	2.759 (2)	161
N1—H1B···O4	0.91	1.93	2.823 (2)	167
N1—H1C···O1^iii	0.91	1.89	2.745 (2)	155
N2—H2A···O4	0.91	1.84	2.746 (2)	172
N2—H2B···O2^iii	0.91	1.91	2.774 (2)	158
N2—H2C···O3^iv	0.91	1.85	2.720 (2)	159

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

(V) bis-rac-1-Phenylethylammonium (R,R)-tartrate(2-)

Crystal data

2(C8H12N)·C4H4O6	F(000) = 840
Mr = 392.44	Dx = 1.271 Mg m^−3
Monoclinic, P21	Synchrotron radiation, λ = 0.6900 Å
Hall symbol: P 2yb	Cell parameters from 5818 reflections
a = 8.3381 (14) Å	θ = 1.7–29.4°
b = 22.738 (4) Å	µ = 0.09 mm^−1
c = 10.8190 (18) Å	T = 150 K
β = 90.120 (3)°	Plate, colourless
V = 2051.2 (6) Å^3	0.30 × 0.22 × 0.06 mm
Z = 4

Data collection

Kappa-CCD diffractometer	5504 reflections with I > 2σ(I)
Radiation source: synchrotron	Rint = 0.034
ϕ scans, and ω scans with κ offsets	θmax = 29.4°, θmin = 1.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.972, Tmax = 0.994	k = −30→30
18641 measured reflections	l = −15→14
5818 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0842P)^2 + 0.5384P] where P = (Fo^2 + 2Fc^2)/3
5818 reflections	(Δ/σ)max = 0.001
517 parameters	Δρmax = 0.59 e Å^−3
1 restraint	Δρmin = −0.34 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O11	0.3959 (2)	0.48525 (10)	0.76691 (19)	0.0302 (4)
O12	0.3469 (2)	0.56775 (9)	0.87050 (17)	0.0259 (4)
O13	0.8339 (2)	0.52948 (11)	1.16414 (19)	0.0325 (4)
O14	0.8851 (2)	0.58334 (11)	0.99741 (18)	0.0299 (4)
O15	0.6974 (2)	0.47686 (9)	0.85069 (17)	0.0257 (4)
H15	0.7620	0.4826	0.7925	0.039*
O16	0.5463 (2)	0.49404 (10)	1.07704 (17)	0.0283 (4)
H16	0.5058	0.5059	1.1436	0.042*
C11	0.4381 (3)	0.52675 (12)	0.8356 (2)	0.0202 (4)
C12	0.6148 (3)	0.52957 (12)	0.8771 (2)	0.0194 (4)
H12	0.6687	0.5626	0.8325	0.023*
C13	0.6220 (3)	0.54174 (12)	1.0160 (2)	0.0205 (4)
H13	0.5588	0.5782	1.0331	0.025*
C14	0.7944 (3)	0.55160 (12)	1.0615 (2)	0.0222 (5)
O21	−0.1309 (2)	0.42473 (10)	0.49823 (19)	0.0281 (4)
O22	−0.0807 (2)	0.47946 (11)	0.66396 (19)	0.0314 (4)
O23	0.3618 (2)	0.52484 (11)	0.27015 (19)	0.0311 (4)
O24	0.4064 (2)	0.44174 (10)	0.37315 (18)	0.0266 (4)
O25	0.2057 (2)	0.51542 (10)	0.57711 (17)	0.0280 (4)
H25	0.2531	0.5029	0.6404	0.042*
O26	0.0582 (2)	0.53313 (10)	0.34984 (17)	0.0267 (4)
H26	−0.0054	0.5275	0.2907	0.040*
C21	−0.0411 (3)	0.45736 (12)	0.5619 (2)	0.0217 (5)
C22	0.1308 (3)	0.46791 (12)	0.5153 (2)	0.0210 (5)
H22	0.1949	0.4316	0.5322	0.025*
C23	0.1396 (3)	0.48055 (12)	0.3772 (2)	0.0205 (4)
H23	0.0860	0.4476	0.3318	0.025*
C24	0.3177 (3)	0.48294 (13)	0.3376 (2)	0.0219 (5)
C31	−0.1566 (4)	0.63264 (14)	0.6447 (3)	0.0328 (6)
C32	−0.2708 (4)	0.66246 (17)	0.7127 (3)	0.0388 (7)
H32	−0.2404	0.6839	0.7844	0.047*
C33	−0.4310 (4)	0.6609 (2)	0.6753 (4)	0.0512 (10)
H33	−0.5092	0.6824	0.7205	0.061*
C34	−0.4772 (5)	0.6286 (2)	0.5735 (5)	0.0615 (13)
H34	−0.5870	0.6266	0.5503	0.074*
C35	−0.3631 (6)	0.5993 (2)	0.5060 (5)	0.0639 (13)
H35	−0.3940	0.5770	0.4355	0.077*
C36	−0.2022 (5)	0.60200 (18)	0.5404 (4)	0.0465 (9)
H36	−0.1234	0.5827	0.4918	0.056*
C37	0.0170 (4)	0.62933 (18)	0.6851 (4)	0.0452 (9)
H37	0.0807	0.6202	0.6092	0.054*
C38	0.0875 (6)	0.6821 (2)	0.7386 (7)	0.0802 (19)
H38A	0.0250	0.6942	0.8109	0.120*
H38B	0.0867	0.7138	0.6771	0.120*
H38C	0.1982	0.6740	0.7637	0.120*
N3	0.0384 (3)	0.57865 (12)	0.7700 (2)	0.0261 (5)
H3A	0.1425	0.5769	0.7953	0.039*
H3B	0.0124	0.5448	0.7299	0.039*
H3C	−0.0264	0.5832	0.8369	0.039*
C41	1.3613 (4)	0.67717 (14)	1.1196 (3)	0.0335 (6)
C42	1.4098 (6)	0.7115 (2)	1.0210 (4)	0.0526 (10)
H42	1.3367	0.7199	0.9559	0.063*
C43	1.5659 (7)	0.7337 (3)	1.0167 (5)	0.0719 (16)
H43	1.5980	0.7574	0.9488	0.086*
C44	1.6709 (5)	0.7220 (2)	1.1075 (5)	0.0642 (14)
H44	1.7768	0.7373	1.1033	0.077*
C45	1.6251 (5)	0.6874 (2)	1.2082 (5)	0.0554 (11)
H45	1.6992	0.6791	1.2727	0.066*
C46	1.4697 (4)	0.66522 (17)	1.2127 (4)	0.0405 (7)
H46	1.4379	0.6416	1.2807	0.049*
C47	1.1919 (3)	0.65292 (15)	1.1208 (3)	0.0346 (6)
H47	1.1327	0.6714	1.0504	0.041*
C48	1.0991 (5)	0.6659 (2)	1.2365 (5)	0.0550 (10)
H48A	0.9940	0.6466	1.2319	0.082*
H48B	1.0844	0.7084	1.2446	0.082*
H48C	1.1582	0.6509	1.3083	0.082*
N4	1.1937 (2)	0.58875 (11)	1.0989 (2)	0.0247 (4)
H4A	1.2372	0.5703	1.1656	0.037*
H4B	1.2534	0.5807	1.0307	0.037*
H4C	1.0916	0.5758	1.0870	0.037*
C51	0.9062 (3)	0.37519 (14)	1.1482 (3)	0.0291 (5)
C52	0.9509 (4)	0.40679 (17)	1.0440 (3)	0.0407 (7)
H52	0.8715	0.4260	0.9956	0.049*
C53	1.1117 (5)	0.4104 (2)	1.0102 (4)	0.0554 (11)
H53	1.1414	0.4329	0.9399	0.066*
C54	1.2278 (5)	0.3818 (2)	1.0775 (4)	0.0549 (11)
H54	1.3372	0.3845	1.0538	0.066*
C55	1.1846 (4)	0.3492 (2)	1.1798 (4)	0.0462 (9)
H55	1.2642	0.3287	1.2257	0.055*
C56	1.0240 (4)	0.34625 (15)	1.2160 (3)	0.0342 (6)
H56	0.9952	0.3243	1.2873	0.041*
C57	0.7335 (3)	0.37795 (15)	1.1905 (3)	0.0320 (6)
H57	0.6638	0.3831	1.1159	0.038*
C58	0.6725 (5)	0.32510 (19)	1.2629 (5)	0.0519 (9)
H58A	0.7399	0.3191	1.3361	0.078*
H58B	0.6767	0.2900	1.2105	0.078*
H58C	0.5615	0.3322	1.2886	0.078*
N5	0.7135 (3)	0.43108 (11)	1.2718 (2)	0.0253 (4)
H5A	0.7819	0.4285	1.3372	0.038*
H5B	0.6107	0.4327	1.2998	0.038*
H5C	0.7357	0.4641	1.2276	0.038*
C61	0.3822 (3)	0.33194 (13)	0.6272 (3)	0.0258 (5)
C62	0.3332 (4)	0.29366 (16)	0.5349 (3)	0.0383 (7)
H62	0.4088	0.2791	0.4769	0.046*
C63	0.1723 (5)	0.27648 (18)	0.5271 (4)	0.0483 (9)
H63	0.1384	0.2505	0.4634	0.058*
C64	0.0641 (4)	0.29712 (18)	0.6111 (4)	0.0443 (8)
H64	−0.0451	0.2856	0.6049	0.053*
C65	0.1114 (4)	0.33474 (17)	0.7053 (3)	0.0375 (7)
H65	0.0353	0.3487	0.7636	0.045*
C66	0.2708 (3)	0.35185 (14)	0.7136 (3)	0.0299 (5)
H66	0.3042	0.3772	0.7785	0.036*
C67	0.5548 (3)	0.35279 (13)	0.6308 (3)	0.0284 (5)
H67	0.6158	0.3311	0.5655	0.034*
C68	0.6369 (4)	0.34175 (17)	0.7547 (3)	0.0395 (7)
H68A	0.7475	0.3563	0.7515	0.059*
H68B	0.6374	0.2995	0.7722	0.059*
H68C	0.5785	0.3624	0.8201	0.059*
N6	0.5620 (3)	0.41681 (11)	0.6017 (2)	0.0242 (4)
H6A	0.5020	0.4243	0.5331	0.036*
H6B	0.6656	0.4274	0.5876	0.036*
H6C	0.5227	0.4377	0.6667	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0221 (8)	0.0434 (12)	0.0253 (9)	0.0001 (8)	−0.0092 (7)	−0.0088 (8)
O12	0.0177 (8)	0.0418 (11)	0.0182 (8)	0.0051 (7)	−0.0033 (6)	−0.0027 (7)
O13	0.0251 (9)	0.0480 (12)	0.0245 (9)	−0.0025 (9)	−0.0135 (7)	0.0026 (9)
O14	0.0169 (8)	0.0512 (13)	0.0214 (9)	−0.0070 (8)	0.0005 (7)	−0.0036 (8)
O15	0.0193 (8)	0.0399 (10)	0.0179 (8)	0.0057 (8)	0.0050 (6)	−0.0013 (7)
O16	0.0193 (8)	0.0532 (13)	0.0123 (7)	−0.0065 (8)	0.0028 (6)	0.0039 (8)
C11	0.0146 (9)	0.0355 (12)	0.0105 (9)	−0.0001 (9)	−0.0029 (7)	0.0020 (8)
C12	0.0138 (9)	0.0318 (12)	0.0124 (9)	−0.0005 (8)	−0.0014 (7)	−0.0001 (8)
C13	0.0115 (9)	0.0375 (13)	0.0125 (9)	0.0005 (8)	−0.0009 (7)	0.0000 (8)
C14	0.0144 (9)	0.0357 (13)	0.0165 (10)	0.0015 (9)	−0.0031 (8)	−0.0051 (9)
O21	0.0163 (8)	0.0467 (12)	0.0214 (9)	−0.0056 (7)	−0.0012 (7)	0.0036 (8)
O22	0.0239 (9)	0.0487 (12)	0.0215 (9)	−0.0013 (9)	0.0115 (7)	−0.0013 (8)
O23	0.0210 (8)	0.0470 (12)	0.0254 (9)	0.0002 (8)	0.0075 (7)	0.0078 (9)
O24	0.0160 (8)	0.0453 (11)	0.0187 (8)	0.0051 (7)	0.0027 (6)	0.0015 (8)
O25	0.0215 (8)	0.0484 (12)	0.0141 (8)	−0.0053 (8)	−0.0034 (6)	−0.0015 (7)
O26	0.0181 (8)	0.0443 (11)	0.0175 (8)	0.0053 (8)	−0.0050 (6)	0.0015 (8)
C21	0.0139 (9)	0.0373 (13)	0.0140 (10)	0.0022 (9)	0.0016 (8)	0.0044 (9)
C22	0.0118 (9)	0.0391 (13)	0.0122 (9)	−0.0002 (8)	0.0008 (7)	0.0012 (9)
C23	0.0148 (9)	0.0340 (12)	0.0128 (9)	0.0000 (9)	0.0007 (7)	−0.0006 (9)
C24	0.0137 (9)	0.0402 (13)	0.0118 (9)	−0.0013 (9)	0.0013 (7)	−0.0024 (9)
C31	0.0274 (13)	0.0401 (16)	0.0308 (14)	−0.0016 (11)	−0.0091 (11)	0.0123 (12)
C32	0.0357 (15)	0.0466 (18)	0.0339 (15)	−0.0011 (13)	−0.0035 (12)	0.0081 (13)
C33	0.0319 (16)	0.066 (2)	0.056 (2)	0.0065 (16)	−0.0001 (15)	0.0201 (19)
C34	0.0330 (17)	0.072 (3)	0.079 (3)	−0.0013 (18)	−0.028 (2)	0.024 (2)
C35	0.073 (3)	0.056 (2)	0.063 (3)	0.001 (2)	−0.046 (2)	0.001 (2)
C36	0.054 (2)	0.049 (2)	0.0372 (17)	0.0129 (16)	−0.0156 (15)	0.0048 (15)
C37	0.0288 (14)	0.059 (2)	0.048 (2)	−0.0080 (14)	−0.0114 (14)	0.0239 (17)
C38	0.047 (2)	0.056 (3)	0.138 (6)	−0.007 (2)	−0.029 (3)	0.011 (3)
N3	0.0175 (9)	0.0439 (13)	0.0168 (9)	0.0031 (9)	−0.0016 (7)	−0.0001 (9)
C41	0.0309 (14)	0.0331 (14)	0.0366 (15)	−0.0045 (11)	0.0027 (11)	−0.0070 (12)
C42	0.061 (2)	0.059 (2)	0.0377 (18)	−0.0229 (19)	0.0007 (17)	0.0011 (16)
C43	0.081 (3)	0.079 (3)	0.056 (3)	−0.046 (3)	0.030 (3)	−0.013 (2)
C44	0.041 (2)	0.072 (3)	0.080 (3)	−0.030 (2)	0.022 (2)	−0.038 (3)
C45	0.0316 (16)	0.063 (3)	0.071 (3)	−0.0060 (16)	−0.0057 (17)	−0.027 (2)
C46	0.0290 (14)	0.0455 (18)	0.0470 (19)	−0.0030 (12)	−0.0024 (13)	−0.0057 (14)
C47	0.0227 (12)	0.0382 (15)	0.0428 (17)	0.0020 (11)	−0.0005 (11)	0.0019 (13)
C48	0.0407 (18)	0.057 (2)	0.068 (3)	0.0023 (17)	0.0136 (18)	−0.021 (2)
N4	0.0155 (9)	0.0393 (12)	0.0191 (9)	−0.0027 (8)	−0.0017 (7)	−0.0028 (9)
C51	0.0246 (12)	0.0395 (14)	0.0232 (12)	0.0062 (11)	0.0013 (10)	−0.0076 (11)
C52	0.0425 (17)	0.055 (2)	0.0246 (14)	0.0156 (15)	0.0084 (12)	−0.0003 (13)
C53	0.058 (2)	0.064 (3)	0.045 (2)	0.011 (2)	0.0290 (18)	−0.0002 (18)
C54	0.0305 (16)	0.073 (3)	0.061 (2)	0.0041 (17)	0.0202 (16)	−0.018 (2)
C55	0.0289 (15)	0.062 (2)	0.0478 (19)	0.0134 (15)	−0.0028 (13)	−0.0133 (17)
C56	0.0289 (13)	0.0421 (16)	0.0318 (14)	0.0069 (12)	−0.0031 (11)	−0.0046 (12)
C57	0.0217 (12)	0.0458 (16)	0.0286 (13)	0.0016 (11)	−0.0024 (10)	−0.0111 (12)
C58	0.0389 (18)	0.049 (2)	0.067 (3)	−0.0070 (15)	0.0103 (18)	−0.0077 (19)
N5	0.0176 (9)	0.0411 (13)	0.0172 (9)	0.0047 (8)	0.0003 (7)	0.0007 (8)
C61	0.0229 (11)	0.0298 (12)	0.0249 (12)	−0.0025 (9)	−0.0001 (9)	0.0024 (10)
C62	0.0402 (16)	0.0428 (17)	0.0319 (15)	−0.0052 (14)	−0.0009 (12)	−0.0054 (13)
C63	0.050 (2)	0.049 (2)	0.046 (2)	−0.0162 (16)	−0.0181 (16)	−0.0024 (15)
C64	0.0326 (15)	0.052 (2)	0.0484 (19)	−0.0163 (14)	−0.0117 (14)	0.0125 (16)
C65	0.0245 (13)	0.0476 (18)	0.0404 (16)	−0.0049 (12)	0.0006 (12)	0.0086 (14)
C66	0.0215 (12)	0.0381 (14)	0.0301 (13)	−0.0021 (10)	0.0004 (10)	0.0000 (11)
C67	0.0187 (11)	0.0358 (14)	0.0306 (13)	0.0018 (10)	0.0027 (9)	−0.0029 (11)
C68	0.0262 (13)	0.0483 (18)	0.0440 (18)	0.0022 (12)	−0.0099 (12)	0.0127 (14)
N6	0.0161 (9)	0.0372 (12)	0.0193 (9)	−0.0025 (8)	0.0017 (7)	0.0014 (8)

Geometric parameters (Å, º)

O11—C11	1.251 (3)	C44—H44	0.95
O12—C11	1.262 (3)	C45—C46	1.392 (5)
O13—C14	1.263 (3)	C45—H45	0.95
O14—C14	1.255 (3)	C46—H46	0.95
O15—C12	1.412 (3)	C47—N4	1.478 (4)
O15—H15	0.84	C47—C48	1.501 (5)
O16—C13	1.419 (3)	C47—H47	1.00
O16—H16	0.84	C48—H48A	0.98
C11—C12	1.541 (3)	C48—H48B	0.98
C12—C13	1.529 (3)	C48—H48C	0.98
C12—H12	1.00	N4—H4A	0.91
C13—C14	1.535 (3)	N4—H4B	0.91
C13—H13	1.00	N4—H4C	0.91
O21—C21	1.259 (3)	C51—C52	1.389 (5)
O22—C21	1.258 (3)	C51—C56	1.390 (4)
O23—C24	1.256 (3)	C51—C57	1.513 (4)
O24—C24	1.253 (3)	C52—C53	1.393 (5)
O25—C22	1.415 (3)	C52—H52	0.95
O25—H25	0.84	C53—C54	1.374 (7)
O26—C23	1.406 (3)	C53—H53	0.95
O26—H26	0.84	C54—C55	1.381 (7)
C21—C22	1.539 (3)	C54—H54	0.95
C22—C23	1.523 (3)	C55—C56	1.397 (5)
C22—H22	1.00	C55—H55	0.95
C23—C24	1.548 (3)	C56—H56	0.95
C23—H23	1.00	C57—N5	1.504 (4)
C31—C36	1.379 (5)	C57—C58	1.523 (6)
C31—C32	1.382 (5)	C57—H57	1.00
C31—C37	1.513 (4)	C58—H58A	0.98
C32—C33	1.396 (5)	C58—H58B	0.98
C32—H32	0.95	C58—H58C	0.98
C33—C34	1.378 (7)	N5—H5A	0.91
C33—H33	0.95	N5—H5B	0.91
C34—C35	1.373 (8)	N5—H5C	0.91
C34—H34	0.95	C61—C62	1.385 (4)
C35—C36	1.393 (6)	C61—C66	1.395 (4)
C35—H35	0.95	C61—C67	1.516 (4)
C36—H36	0.95	C62—C63	1.400 (5)
C37—C38	1.456 (7)	C62—H62	0.95
C37—N3	1.485 (4)	C63—C64	1.365 (6)
C37—H37	1.00	C63—H63	0.95
C38—H38A	0.98	C64—C65	1.387 (5)
C38—H38B	0.98	C64—H64	0.95
C38—H38C	0.98	C65—C66	1.387 (4)
N3—H3A	0.91	C65—H65	0.95
N3—H3B	0.91	C66—H66	0.95
N3—H3C	0.91	C67—N6	1.490 (4)
C41—C46	1.379 (5)	C67—C68	1.525 (4)
C41—C42	1.382 (5)	C67—H67	1.00
C41—C47	1.517 (4)	C68—H68A	0.98
C42—C43	1.398 (6)	C68—H68B	0.98
C42—H42	0.95	C68—H68C	0.98
C43—C44	1.341 (9)	N6—H6A	0.91
C43—H43	0.95	N6—H6B	0.91
C44—C45	1.397 (8)	N6—H6C	0.91
C12—O15—H15	109.5	C41—C46—H46	119.6
C13—O16—H16	109.5	C45—C46—H46	119.6
O11—C11—O12	124.5 (2)	N4—C47—C48	109.4 (3)
O11—C11—C12	118.2 (2)	N4—C47—C41	110.3 (2)
O12—C11—C12	117.3 (2)	C48—C47—C41	114.7 (3)
O15—C12—C13	109.5 (2)	N4—C47—H47	107.4
O15—C12—C11	111.8 (2)	C48—C47—H47	107.4
C13—C12—C11	109.22 (18)	C41—C47—H47	107.4
O15—C12—H12	108.7	C47—C48—H48A	109.5
C13—C12—H12	108.7	C47—C48—H48B	109.5
C11—C12—H12	108.7	H48A—C48—H48B	109.5
O16—C13—C12	107.6 (2)	C47—C48—H48C	109.5
O16—C13—C14	112.3 (2)	H48A—C48—H48C	109.5
C12—C13—C14	112.09 (19)	H48B—C48—H48C	109.5
O16—C13—H13	108.2	C47—N4—H4A	109.5
C12—C13—H13	108.2	C47—N4—H4B	109.5
C14—C13—H13	108.2	H4A—N4—H4B	109.5
O14—C14—O13	123.9 (2)	C47—N4—H4C	109.5
O14—C14—C13	118.2 (2)	H4A—N4—H4C	109.5
O13—C14—C13	117.8 (2)	H4B—N4—H4C	109.5
C22—O25—H25	109.5	C52—C51—C56	118.8 (3)
C23—O26—H26	109.5	C52—C51—C57	118.7 (3)
O22—C21—O21	124.0 (2)	C56—C51—C57	122.2 (3)
O22—C21—C22	118.2 (2)	C51—C52—C53	120.3 (3)
O21—C21—C22	117.8 (2)	C51—C52—H52	119.9
O25—C22—C23	107.3 (2)	C53—C52—H52	119.9
O25—C22—C21	112.0 (2)	C54—C53—C52	120.7 (4)
C23—C22—C21	113.43 (19)	C54—C53—H53	119.7
O25—C22—H22	108.0	C52—C53—H53	119.7
C23—C22—H22	108.0	C53—C54—C55	119.6 (3)
C21—C22—H22	108.0	C53—C54—H54	120.2
O26—C23—C22	110.1 (2)	C55—C54—H54	120.2
O26—C23—C24	112.0 (2)	C54—C55—C56	120.1 (4)
C22—C23—C24	109.03 (18)	C54—C55—H55	119.9
O26—C23—H23	108.6	C56—C55—H55	119.9
C22—C23—H23	108.6	C51—C56—C55	120.4 (3)
C24—C23—H23	108.6	C51—C56—H56	119.8
O24—C24—O23	124.9 (2)	C55—C56—H56	119.8
O24—C24—C23	117.0 (2)	N5—C57—C51	108.5 (2)
O23—C24—C23	118.0 (2)	N5—C57—C58	107.2 (3)
C36—C31—C32	119.6 (3)	C51—C57—C58	116.2 (3)
C36—C31—C37	118.2 (3)	N5—C57—H57	108.2
C32—C31—C37	122.1 (3)	C51—C57—H57	108.2
C31—C32—C33	119.6 (4)	C58—C57—H57	108.2
C31—C32—H32	120.2	C57—C58—H58A	109.5
C33—C32—H32	120.2	C57—C58—H58B	109.5
C34—C33—C32	120.7 (4)	H58A—C58—H58B	109.5
C34—C33—H33	119.7	C57—C58—H58C	109.5
C32—C33—H33	119.7	H58A—C58—H58C	109.5
C35—C34—C33	119.4 (4)	H58B—C58—H58C	109.5
C35—C34—H34	120.3	C57—N5—H5A	109.5
C33—C34—H34	120.3	C57—N5—H5B	109.5
C34—C35—C36	120.3 (4)	H5A—N5—H5B	109.5
C34—C35—H35	119.9	C57—N5—H5C	109.5
C36—C35—H35	119.9	H5A—N5—H5C	109.5
C31—C36—C35	120.3 (4)	H5B—N5—H5C	109.5
C31—C36—H36	119.8	C62—C61—C66	119.4 (3)
C35—C36—H36	119.8	C62—C61—C67	119.6 (3)
C38—C37—N3	110.3 (4)	C66—C61—C67	121.0 (3)
C38—C37—C31	117.3 (4)	C61—C62—C63	120.0 (3)
N3—C37—C31	109.3 (3)	C61—C62—H62	120.0
C38—C37—H37	106.4	C63—C62—H62	120.0
N3—C37—H37	106.4	C64—C63—C62	119.9 (3)
C31—C37—H37	106.4	C64—C63—H63	120.0
C37—C38—H38A	109.5	C62—C63—H63	120.0
C37—C38—H38B	109.5	C63—C64—C65	120.9 (3)
H38A—C38—H38B	109.5	C63—C64—H64	119.5
C37—C38—H38C	109.5	C65—C64—H64	119.5
H38A—C38—H38C	109.5	C66—C65—C64	119.4 (3)
H38B—C38—H38C	109.5	C66—C65—H65	120.3
C37—N3—H3A	109.5	C64—C65—H65	120.3
C37—N3—H3B	109.5	C65—C66—C61	120.3 (3)
H3A—N3—H3B	109.5	C65—C66—H66	119.9
C37—N3—H3C	109.5	C61—C66—H66	119.9
H3A—N3—H3C	109.5	N6—C67—C61	109.8 (2)
H3B—N3—H3C	109.5	N6—C67—C68	109.2 (3)
C46—C41—C42	118.8 (3)	C61—C67—C68	113.3 (3)
C46—C41—C47	122.1 (3)	N6—C67—H67	108.2
C42—C41—C47	119.1 (3)	C61—C67—H67	108.2
C41—C42—C43	120.2 (4)	C68—C67—H67	108.2
C41—C42—H42	119.9	C67—C68—H68A	109.5
C43—C42—H42	119.9	C67—C68—H68B	109.5
C44—C43—C42	120.7 (5)	H68A—C68—H68B	109.5
C44—C43—H43	119.6	C67—C68—H68C	109.5
C42—C43—H43	119.6	H68A—C68—H68C	109.5
C43—C44—C45	120.2 (4)	H68B—C68—H68C	109.5
C43—C44—H44	119.9	C67—N6—H6A	109.5
C45—C44—H44	119.9	C67—N6—H6B	109.5
C46—C45—C44	119.2 (4)	H6A—N6—H6B	109.5
C46—C45—H45	120.4	C67—N6—H6C	109.5
C44—C45—H45	120.4	H6A—N6—H6C	109.5
C41—C46—C45	120.8 (4)	H6B—N6—H6C	109.5
O11—C11—C12—O15	−12.3 (3)	C46—C41—C42—C43	−0.3 (6)
O12—C11—C12—O15	169.8 (2)	C47—C41—C42—C43	−179.1 (4)
O11—C11—C12—C13	−133.7 (2)	C41—C42—C43—C44	0.3 (8)
O12—C11—C12—C13	48.4 (3)	C42—C43—C44—C45	−0.2 (8)
O15—C12—C13—O16	−60.8 (2)	C43—C44—C45—C46	0.2 (7)
C11—C12—C13—O16	62.0 (3)	C42—C41—C46—C45	0.3 (6)
O15—C12—C13—C14	63.2 (3)	C47—C41—C46—C45	179.1 (3)
C11—C12—C13—C14	−174.0 (2)	C44—C45—C46—C41	−0.2 (6)
O16—C13—C14—O14	164.7 (2)	C46—C41—C47—N4	−70.2 (4)
C12—C13—C14—O14	43.4 (3)	C42—C41—C47—N4	108.6 (4)
O16—C13—C14—O13	−18.5 (3)	C46—C41—C47—C48	53.9 (5)
C12—C13—C14—O13	−139.9 (3)	C42—C41—C47—C48	−127.3 (4)
O22—C21—C22—O25	−17.4 (3)	C56—C51—C52—C53	−1.6 (5)
O21—C21—C22—O25	165.9 (2)	C57—C51—C52—C53	173.0 (4)
O22—C21—C22—C23	−139.0 (3)	C51—C52—C53—C54	1.5 (7)
O21—C21—C22—C23	44.3 (3)	C52—C53—C54—C55	−0.1 (7)
O25—C22—C23—O26	−60.7 (2)	C53—C54—C55—C56	−1.2 (6)
C21—C22—C23—O26	63.5 (3)	C52—C51—C56—C55	0.2 (5)
O25—C22—C23—C24	62.6 (3)	C57—C51—C56—C55	−174.2 (3)
C21—C22—C23—C24	−173.2 (2)	C54—C55—C56—C51	1.2 (6)
O26—C23—C24—O24	170.3 (2)	C52—C51—C57—N5	−85.7 (3)
C22—C23—C24—O24	48.3 (3)	C56—C51—C57—N5	88.7 (4)
O26—C23—C24—O23	−11.5 (3)	C52—C51—C57—C58	153.6 (3)
C22—C23—C24—O23	−133.5 (2)	C56—C51—C57—C58	−32.0 (4)
C36—C31—C32—C33	0.4 (5)	C66—C61—C62—C63	1.6 (5)
C37—C31—C32—C33	−175.9 (3)	C67—C61—C62—C63	−176.8 (3)
C31—C32—C33—C34	1.9 (6)	C61—C62—C63—C64	−0.5 (6)
C32—C33—C34—C35	−2.2 (7)	C62—C63—C64—C65	−0.5 (6)
C33—C34—C35—C36	0.3 (7)	C63—C64—C65—C66	0.4 (6)
C32—C31—C36—C35	−2.3 (6)	C64—C65—C66—C61	0.7 (5)
C37—C31—C36—C35	174.1 (4)	C62—C61—C66—C65	−1.7 (5)
C34—C35—C36—C31	2.0 (7)	C67—C61—C66—C65	176.7 (3)
C36—C31—C37—C38	144.2 (5)	C62—C61—C67—N6	112.0 (3)
C32—C31—C37—C38	−39.5 (6)	C66—C61—C67—N6	−66.4 (3)
C36—C31—C37—N3	−89.3 (4)	C62—C61—C67—C68	−125.7 (3)
C32—C31—C37—N3	87.0 (4)	C66—C61—C67—C68	55.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O15—H15···O22^i	0.84	1.91	2.743 (3)	169
O16—H16···O23^ii	0.84	1.87	2.690 (3)	164
O25—H25···O11	0.84	1.86	2.681 (3)	167
O26—H26···O13^iii	0.84	1.91	2.743 (3)	169
N3—H3A···O12	0.91	1.90	2.801 (3)	171
N3—H3B···O22	0.91	1.82	2.718 (4)	168
N3—H3C···O14^iv	0.91	1.89	2.777 (3)	165
N4—H4A···O23^v	0.91	1.85	2.738 (3)	165
N4—H4B···O12^i	0.91	1.92	2.825 (3)	170
N4—H4C···O14	0.91	1.98	2.798 (3)	149
N5—H5A···O21^v	0.91	1.89	2.774 (3)	164
N5—H5B···O24^ii	0.91	1.89	2.798 (3)	173
N5—H5C···O13	0.91	1.83	2.716 (3)	164
N6—H6A···O24	0.91	1.95	2.847 (3)	171
N6—H6B···O21^i	0.91	1.96	2.803 (3)	154
N6—H6C···O11	0.91	1.86	2.747 (3)	164

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

(VI) bis-(R)-1.Phenylethylammonium rac-tartrate(2-)

Crystal data

4(C8H12N)·2(C4H4O6)·CH4O	Z = 2
Mr = 816.93	F(000) = 876
Triclinic, P1	Dx = 1.267 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0822 (3) Å	Cell parameters from 9771 reflections
b = 15.7819 (5) Å	θ = 2.6–27.6°
c = 15.9040 (5) Å	µ = 0.09 mm^−1
α = 108.7460 (15)°	T = 150 K
β = 96.858 (2)°	Plate, colourless
γ = 90.0600 (18)°	0.20 × 0.16 × 0.08 mm
V = 2141.33 (12) Å^3

Data collection

Kappa-CCD diffractometer	9771 independent reflections
Radiation source: fine-focus sealed X-ray tube	6899 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
ϕ scans, and ω scans with κ offsets	θmax = 27.6°, θmin = 2.6°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.975, Tmax = 0.993	k = −20→17
28530 measured reflections	l = −19→20

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)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.066P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
9771 reflections	Δρmax = 0.44 e Å^−3
1074 parameters	Δρmin = −0.40 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: 0.0191 (18)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O12	−0.1286 (3)	0.32807 (17)	0.43058 (18)	0.0309 (6)
O11	0.0193 (3)	0.21248 (17)	0.40497 (19)	0.0305 (6)
O13	0.4229 (3)	0.37649 (19)	0.34477 (19)	0.0373 (7)
O14	0.4236 (4)	0.4723 (2)	0.4833 (2)	0.0473 (8)
O15	0.0711 (3)	0.43776 (17)	0.40486 (19)	0.0302 (6)
H15	0.0292	0.4546	0.4515	0.045*
O16	0.2454 (3)	0.36508 (17)	0.53131 (17)	0.0293 (6)
H16	0.3115	0.3414	0.5569	0.044*
C11	−0.0084 (4)	0.2922 (3)	0.4104 (2)	0.0259 (8)
C12	0.1113 (4)	0.3475 (2)	0.3882 (3)	0.0260 (8)
H12D	0.1191	0.3211	0.3228	0.031*
C13	0.2625 (4)	0.3419 (3)	0.4389 (3)	0.0276 (8)
H13A	0.2935	0.2785	0.4177	0.033*
C14	0.3806 (4)	0.4019 (3)	0.4216 (3)	0.0312 (9)
O21	0.4854 (3)	0.28847 (17)	0.59234 (19)	0.0328 (6)
O22	0.6239 (3)	0.16811 (18)	0.56818 (18)	0.0315 (6)
O23	0.0848 (3)	0.13457 (18)	0.66674 (18)	0.0312 (6)
O24	0.0449 (5)	0.0494 (3)	0.5243 (2)	0.0709 (12)
O25	0.4190 (3)	0.06888 (17)	0.60625 (19)	0.0317 (6)
H25	0.4599	0.0472	0.5597	0.048*
O26	0.2503 (3)	0.13390 (18)	0.47096 (17)	0.0292 (6)
H26	0.1817	0.1536	0.4430	0.044*
C21	0.5070 (4)	0.2087 (3)	0.5888 (2)	0.0270 (8)
C22	0.3844 (4)	0.1587 (2)	0.6159 (3)	0.0266 (8)
H22A	0.3771	0.1900	0.6807	0.032*
C23	0.2350 (4)	0.1642 (2)	0.5640 (2)	0.0245 (8)
H23A	0.2081	0.2284	0.5812	0.029*
C24	0.1128 (4)	0.1106 (3)	0.5867 (3)	0.0294 (8)
O31	0.5630 (3)	0.79291 (17)	0.60979 (18)	0.0304 (6)
O32	0.4034 (3)	0.67865 (17)	0.58923 (18)	0.0297 (6)
O33	0.9854 (3)	0.6271 (2)	0.6763 (2)	0.0394 (7)
O34	0.9327 (4)	0.5333 (2)	0.5377 (2)	0.0477 (8)
O35	0.6137 (3)	0.56940 (17)	0.61649 (19)	0.0306 (6)
H35	0.5567	0.5507	0.5681	0.046*
O36	0.7363 (3)	0.64020 (18)	0.48814 (17)	0.0292 (6)
H36	0.7971	0.6585	0.4613	0.044*
C31	0.5313 (4)	0.7143 (2)	0.6074 (2)	0.0257 (8)
C32	0.6613 (4)	0.6601 (2)	0.6317 (3)	0.0268 (8)
H32A	0.6958	0.6877	0.6971	0.032*
C33	0.7913 (4)	0.6646 (3)	0.5811 (3)	0.0267 (8)
H33A	0.8328	0.7277	0.6019	0.032*
C34	0.9147 (4)	0.6032 (3)	0.5990 (3)	0.0310 (9)
O41	0.9463 (3)	0.71289 (17)	0.41826 (19)	0.0317 (6)
O42	1.0950 (3)	0.83235 (18)	0.43839 (18)	0.0302 (6)
O43	0.5133 (3)	0.86458 (19)	0.34099 (19)	0.0348 (6)
O44	0.5368 (5)	0.9517 (3)	0.4810 (2)	0.0829 (15)
O45	0.8738 (3)	0.93122 (17)	0.40015 (19)	0.0319 (6)
H45	0.9348	0.9533	0.4464	0.048*
O46	0.7622 (3)	0.86603 (18)	0.53609 (17)	0.0315 (6)
H46	0.7074	0.8445	0.5638	0.047*
C41	0.9695 (4)	0.7924 (3)	0.4192 (3)	0.0273 (8)
C42	0.8350 (4)	0.8415 (2)	0.3916 (3)	0.0253 (8)
H42A	0.8010	0.8097	0.3269	0.030*
C43	0.7074 (4)	0.8360 (3)	0.4431 (3)	0.0258 (8)
H43A	0.6734	0.7717	0.4258	0.031*
C44	0.5759 (4)	0.8889 (3)	0.4201 (3)	0.0306 (9)
N5	0.7932 (4)	1.0526 (2)	0.6477 (2)	0.0302 (7)
H5A	0.8883	1.0752	0.6575	0.045*
H5B	0.7349	1.0819	0.6163	0.045*
H5C	0.7905	0.9932	0.6158	0.045*
C51	0.8325 (4)	1.0195 (3)	0.7922 (3)	0.0322 (9)
C52	0.9587 (5)	1.0616 (3)	0.8495 (3)	0.0410 (10)
H52	0.9884	1.1203	0.8524	0.049*
C53	1.0416 (5)	1.0196 (4)	0.9023 (3)	0.0508 (12)
H53	1.1275	1.0492	0.9407	0.061*
C54	0.9988 (6)	0.9348 (4)	0.8987 (3)	0.0542 (13)
H54	1.0552	0.9060	0.9351	0.065*
C55	0.8754 (6)	0.8916 (4)	0.8431 (4)	0.0549 (13)
H55	0.8469	0.8329	0.8410	0.066*
C56	0.7910 (5)	0.9335 (3)	0.7894 (3)	0.0427 (10)
H56	0.7055	0.9033	0.7511	0.051*
C57	0.7368 (4)	1.0653 (3)	0.7365 (3)	0.0314 (9)
H57	0.6348	1.0365	0.7236	0.038*
C58	0.7233 (5)	1.1647 (3)	0.7827 (3)	0.0440 (11)
H58A	0.6889	1.1742	0.8410	0.066*
H58B	0.6518	1.1885	0.7457	0.066*
H58C	0.8203	1.1955	0.7912	0.066*
N6	0.7723 (3)	1.1132 (2)	0.4118 (2)	0.0279 (7)
H6A	0.7806	1.0536	0.4025	0.042*
H6B	0.7292	1.1385	0.4624	0.042*
H6C	0.8641	1.1394	0.4181	0.042*
C61	0.7167 (4)	1.0619 (3)	0.2471 (3)	0.0314 (9)
C62	0.6992 (4)	0.9701 (3)	0.2277 (3)	0.0338 (9)
H62	0.6619	0.9472	0.2697	0.041*
C63	0.7353 (5)	0.9109 (3)	0.1476 (3)	0.0388 (10)
H63	0.7252	0.8481	0.1358	0.047*
C64	0.7861 (5)	0.9443 (3)	0.0852 (3)	0.0442 (11)
H64	0.8104	0.9042	0.0303	0.053*
C65	0.8017 (5)	1.0358 (3)	0.1024 (3)	0.0455 (11)
H65	0.8357	1.0583	0.0592	0.055*
C66	0.7676 (5)	1.0949 (3)	0.1832 (3)	0.0383 (10)
H66	0.7788	1.1576	0.1950	0.046*
C67	0.6783 (4)	1.1269 (3)	0.3333 (3)	0.0343 (9)
H67	0.7018	1.1887	0.3331	0.041*
C68	0.5173 (5)	1.1218 (3)	0.3457 (3)	0.0478 (11)
H68A	0.4555	1.1318	0.2951	0.072*
H68B	0.4993	1.1678	0.4014	0.072*
H68C	0.4921	1.0625	0.3486	0.072*
N7	1.2288 (4)	0.9470 (2)	0.3590 (2)	0.0300 (7)
H7A	1.3211	0.9273	0.3484	0.045*
H7B	1.1867	0.9146	0.3887	0.045*
H7C	1.2359	1.0059	0.3929	0.045*
C71	1.1992 (4)	0.9896 (3)	0.2205 (3)	0.0301 (8)
C72	1.3086 (5)	0.9576 (3)	0.1651 (3)	0.0368 (9)
H72	1.3485	0.9009	0.1607	0.044*
C73	1.3597 (5)	1.0075 (3)	0.1167 (3)	0.0423 (10)
H73	1.4348	0.9849	0.0796	0.051*
C74	1.3029 (5)	1.0897 (3)	0.1215 (3)	0.0416 (10)
H74	1.3377	1.1233	0.0874	0.050*
C75	1.1952 (5)	1.1228 (3)	0.1763 (3)	0.0422 (10)
H75	1.1565	1.1796	0.1804	0.051*
C76	1.1433 (5)	1.0734 (3)	0.2256 (3)	0.0359 (9)
H76	1.0691	1.0967	0.2631	0.043*
C77	1.1343 (4)	0.9359 (3)	0.2716 (3)	0.0323 (9)
H77	1.0350	0.9599	0.2856	0.039*
C78	1.1111 (5)	0.8373 (3)	0.2201 (3)	0.0449 (11)
H78A	1.0552	0.8294	0.1612	0.067*
H78B	1.0554	0.8083	0.2532	0.067*
H78C	1.2077	0.8101	0.2123	0.067*
N8	0.2635 (4)	0.5499 (2)	0.6500 (2)	0.0302 (7)
H8A	0.1742	0.5718	0.6651	0.045*
H8B	0.2487	0.4970	0.6044	0.045*
H8C	0.3136	0.5898	0.6323	0.045*
C81	0.3805 (4)	0.6202 (3)	0.8072 (3)	0.0319 (8)
C82	0.2649 (5)	0.6701 (3)	0.8462 (3)	0.0441 (10)
H82	0.1652	0.6545	0.8193	0.053*
C83	0.2955 (6)	0.7427 (3)	0.9242 (3)	0.0545 (13)
H83	0.2167	0.7762	0.9510	0.065*
C84	0.4418 (6)	0.7662 (3)	0.9631 (3)	0.0553 (13)
H84	0.4627	0.8150	1.0172	0.066*
C85	0.5558 (6)	0.7188 (3)	0.9233 (3)	0.0562 (13)
H85	0.6556	0.7356	0.9492	0.067*
C86	0.5256 (5)	0.6464 (3)	0.8454 (3)	0.0440 (11)
H86	0.6052	0.6145	0.8179	0.053*
C87	0.3522 (4)	0.5351 (3)	0.7295 (3)	0.0303 (8)
H87	0.4506	0.5127	0.7116	0.036*
C88	0.2734 (5)	0.4620 (3)	0.7542 (3)	0.0366 (9)
H88A	0.3361	0.4476	0.8019	0.055*
H88B	0.2549	0.4082	0.7015	0.055*
H88C	0.1787	0.4835	0.7750	0.055*
N9	0.1975 (4)	0.6085 (2)	0.4275 (2)	0.0297 (7)
H9A	0.1218	0.6438	0.4190	0.045*
H9B	0.2498	0.6345	0.4825	0.045*
H9C	0.1599	0.5538	0.4239	0.045*
C91	0.2154 (4)	0.5588 (3)	0.2637 (3)	0.0312 (9)
C92	0.1000 (5)	0.6014 (3)	0.2300 (3)	0.0410 (10)
H92	0.0627	0.6538	0.2688	0.049*
C93	0.0389 (6)	0.5691 (3)	0.1415 (3)	0.0510 (12)
H93	−0.0397	0.5993	0.1199	0.061*
C94	0.0917 (6)	0.4929 (3)	0.0843 (3)	0.0529 (12)
H94	0.0508	0.4712	0.0230	0.063*
C95	0.2040 (5)	0.4484 (3)	0.1164 (3)	0.0487 (12)
H95	0.2410	0.3962	0.0772	0.058*
C96	0.2628 (4)	0.4798 (3)	0.2057 (3)	0.0379 (10)
H96	0.3366	0.4471	0.2278	0.045*
C97	0.2989 (4)	0.5977 (3)	0.3563 (3)	0.0297 (8)
H97	0.3782	0.5561	0.3644	0.036*
C98	0.3717 (4)	0.6887 (3)	0.3692 (3)	0.0323 (9)
H98A	0.4420	0.6821	0.3255	0.049*
H98B	0.4248	0.7125	0.4299	0.049*
H98C	0.2954	0.7299	0.3605	0.049*
N10	0.7098 (4)	0.4554 (2)	0.3678 (2)	0.0288 (7)
H10A	0.7144	0.5074	0.4145	0.043*
H10B	0.7664	0.4145	0.3843	0.043*
H10C	0.6140	0.4339	0.3519	0.043*
C101	0.7631 (4)	0.3867 (3)	0.2105 (3)	0.0329 (9)
C102	0.6311 (5)	0.3389 (3)	0.1696 (3)	0.0479 (11)
H102	0.5418	0.3551	0.1952	0.058*
C103	0.6301 (6)	0.2670 (3)	0.0906 (3)	0.0560 (13)
H103	0.5397	0.2344	0.0625	0.067*
C104	0.7591 (6)	0.2428 (3)	0.0530 (3)	0.0513 (12)
H104	0.7573	0.1947	−0.0016	0.062*
C105	0.8908 (6)	0.2887 (3)	0.0952 (3)	0.0530 (12)
H105	0.9805	0.2712	0.0704	0.064*
C106	0.8927 (5)	0.3605 (3)	0.1740 (3)	0.0422 (10)
H106	0.9839	0.3917	0.2028	0.051*
C107	0.7667 (4)	0.4725 (3)	0.2900 (3)	0.0298 (8)
H107	0.8725	0.4949	0.3088	0.036*
C108	0.6793 (5)	0.5453 (3)	0.2653 (3)	0.0373 (9)
H10D	0.5756	0.5242	0.2448	0.056*
H10E	0.7222	0.5593	0.2174	0.056*
H10F	0.6838	0.5992	0.3179	0.056*
N11	0.3122 (4)	−0.1098 (2)	0.5935 (2)	0.0292 (7)
H11A	0.2482	−0.1340	0.5426	0.044*
H11B	0.3997	−0.1379	0.5878	0.044*
H11C	0.3286	−0.0504	0.6026	0.044*
C111	0.3322 (5)	−0.0623 (3)	0.7581 (3)	0.0335 (9)
C112	0.3330 (5)	0.0309 (3)	0.7847 (3)	0.0395 (10)
H112	0.2780	0.0593	0.7475	0.047*
C113	0.4122 (5)	0.0826 (3)	0.8643 (3)	0.0404 (10)
H113	0.4114	0.1460	0.8813	0.049*
C114	0.4926 (5)	0.0425 (3)	0.9191 (3)	0.0419 (10)
H114	0.5476	0.0780	0.9737	0.050*
C115	0.4923 (5)	−0.0502 (3)	0.8937 (3)	0.0458 (11)
H115	0.5472	−0.0781	0.9315	0.055*
C116	0.4133 (5)	−0.1025 (3)	0.8142 (3)	0.0395 (10)
H116	0.4141	−0.1659	0.7977	0.047*
C117	0.2462 (5)	−0.1215 (3)	0.6721 (3)	0.0391 (10)
H117	0.2586	−0.1850	0.6701	0.047*
C118	0.0870 (5)	−0.1064 (4)	0.6636 (3)	0.0528 (12)
H11D	0.0470	−0.1080	0.7176	0.079*
H11E	0.0366	−0.1532	0.6114	0.079*
H11F	0.0708	−0.0477	0.6560	0.079*
N12	0.7332 (3)	0.3980 (2)	0.5934 (2)	0.0295 (7)
H12A	0.6605	0.3603	0.5974	0.044*
H12B	0.7678	0.3755	0.5395	0.044*
H12C	0.6956	0.4527	0.5986	0.044*
C121	0.8077 (5)	0.4427 (3)	0.7591 (3)	0.0341 (9)
C122	0.7022 (5)	0.3963 (3)	0.7861 (3)	0.0448 (11)
H122	0.6525	0.3440	0.7443	0.054*
C123	0.6689 (6)	0.4259 (4)	0.8738 (4)	0.0577 (13)
H123	0.5967	0.3939	0.8916	0.069*
C124	0.7402 (6)	0.5012 (4)	0.9342 (4)	0.0597 (15)
H124	0.7190	0.5205	0.9944	0.072*
C125	0.8429 (6)	0.5494 (4)	0.9084 (3)	0.0580 (14)
H125	0.8906	0.6022	0.9505	0.070*
C126	0.8765 (5)	0.5210 (3)	0.8215 (3)	0.0441 (10)
H126	0.9465	0.5547	0.8039	0.053*
C127	0.8584 (4)	0.4074 (3)	0.6675 (3)	0.0299 (8)
H127	0.9347	0.4511	0.6633	0.036*
C128	0.9282 (4)	0.3173 (3)	0.6511 (3)	0.0367 (9)
H12E	1.0124	0.3222	0.6973	0.055*
H12F	0.9630	0.2985	0.5920	0.055*
H12G	0.8545	0.2729	0.6532	0.055*
O1	0.2387 (6)	0.2634 (3)	0.8082 (3)	0.0857 (13)
H1	0.1817	0.2267	0.7671	0.129*
C1	0.1652 (10)	0.3027 (6)	0.8748 (5)	0.109 (3)
H1A	0.2212	0.3569	0.9143	0.164*
H1B	0.1510	0.2618	0.9086	0.164*
H1C	0.0683	0.3190	0.8517	0.164*
O2	0.5884 (5)	0.7303 (3)	0.1910 (3)	0.0862 (14)
H2	0.5541	0.7735	0.2289	0.129*
C2	0.4731 (12)	0.6745 (6)	0.1372 (6)	0.115 (3)
H2A	0.4381	0.6355	0.1685	0.173*
H2B	0.5078	0.6378	0.0814	0.173*
H2C	0.3916	0.7106	0.1237	0.173*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O12	0.0239 (14)	0.0272 (14)	0.0409 (16)	0.0028 (11)	0.0060 (11)	0.0093 (12)
O11	0.0237 (13)	0.0246 (15)	0.0435 (16)	0.0023 (11)	0.0047 (12)	0.0113 (12)
O13	0.0316 (15)	0.0381 (17)	0.0410 (17)	−0.0022 (12)	0.0089 (13)	0.0097 (13)
O14	0.0499 (19)	0.0361 (18)	0.0464 (19)	−0.0219 (14)	0.0033 (15)	0.0015 (15)
O15	0.0243 (14)	0.0279 (14)	0.0421 (17)	0.0045 (11)	0.0085 (12)	0.0149 (13)
O16	0.0302 (15)	0.0262 (14)	0.0323 (15)	0.0011 (11)	0.0028 (11)	0.0109 (12)
C11	0.0246 (19)	0.025 (2)	0.027 (2)	0.0008 (15)	0.0008 (15)	0.0084 (15)
C12	0.0193 (18)	0.0232 (19)	0.036 (2)	0.0015 (14)	0.0052 (15)	0.0092 (16)
C13	0.0239 (19)	0.0233 (19)	0.033 (2)	0.0024 (15)	0.0055 (16)	0.0050 (16)
C14	0.0212 (19)	0.030 (2)	0.047 (3)	0.0021 (15)	0.0041 (17)	0.019 (2)
O21	0.0283 (14)	0.0235 (15)	0.0466 (17)	−0.0030 (11)	−0.0025 (12)	0.0137 (12)
O22	0.0254 (14)	0.0356 (15)	0.0372 (15)	0.0045 (11)	0.0068 (11)	0.0159 (13)
O23	0.0292 (15)	0.0315 (15)	0.0332 (16)	0.0010 (11)	0.0093 (12)	0.0088 (12)
O24	0.084 (3)	0.073 (3)	0.043 (2)	−0.053 (2)	0.0091 (19)	0.0012 (18)
O25	0.0324 (15)	0.0243 (14)	0.0415 (17)	0.0038 (11)	0.0085 (12)	0.0138 (12)
O26	0.0259 (14)	0.0346 (15)	0.0269 (14)	0.0025 (11)	0.0008 (11)	0.0107 (12)
C21	0.0218 (19)	0.032 (2)	0.0252 (19)	−0.0023 (15)	−0.0017 (14)	0.0087 (16)
C22	0.029 (2)	0.0191 (18)	0.030 (2)	0.0035 (15)	0.0023 (16)	0.0061 (15)
C23	0.0206 (18)	0.0231 (19)	0.030 (2)	0.0011 (14)	0.0020 (15)	0.0091 (16)
C24	0.0259 (19)	0.025 (2)	0.033 (2)	−0.0020 (15)	−0.0006 (16)	0.0063 (17)
O31	0.0260 (14)	0.0232 (14)	0.0432 (16)	0.0020 (10)	0.0057 (12)	0.0120 (12)
O32	0.0261 (14)	0.0242 (14)	0.0386 (15)	−0.0003 (11)	0.0024 (12)	0.0103 (12)
O33	0.0325 (16)	0.0440 (18)	0.0383 (17)	0.0071 (13)	−0.0038 (13)	0.0115 (14)
O34	0.0496 (19)	0.0384 (18)	0.0453 (18)	0.0191 (14)	0.0012 (14)	0.0014 (14)
O35	0.0268 (14)	0.0231 (14)	0.0422 (17)	−0.0006 (11)	0.0012 (12)	0.0121 (12)
O36	0.0261 (14)	0.0313 (15)	0.0304 (15)	−0.0006 (11)	0.0024 (11)	0.0107 (12)
C31	0.0238 (19)	0.025 (2)	0.029 (2)	0.0032 (15)	0.0063 (15)	0.0095 (16)
C32	0.0200 (18)	0.027 (2)	0.033 (2)	0.0007 (15)	0.0019 (15)	0.0098 (16)
C33	0.0217 (18)	0.0224 (19)	0.034 (2)	−0.0007 (14)	−0.0004 (15)	0.0071 (16)
C34	0.0233 (19)	0.025 (2)	0.046 (2)	0.0023 (15)	0.0044 (17)	0.0121 (18)
O41	0.0285 (14)	0.0252 (15)	0.0425 (16)	0.0039 (11)	0.0067 (12)	0.0116 (12)
O42	0.0207 (13)	0.0354 (15)	0.0348 (15)	0.0006 (11)	0.0022 (11)	0.0121 (12)
O43	0.0264 (14)	0.0358 (16)	0.0433 (17)	0.0048 (11)	0.0003 (12)	0.0159 (13)
O44	0.099 (3)	0.080 (3)	0.046 (2)	0.067 (3)	−0.005 (2)	−0.0083 (19)
O45	0.0286 (15)	0.0247 (14)	0.0439 (17)	−0.0010 (11)	−0.0025 (12)	0.0156 (13)
O46	0.0297 (15)	0.0344 (15)	0.0317 (15)	−0.0010 (12)	0.0036 (12)	0.0124 (12)
C41	0.0231 (19)	0.027 (2)	0.030 (2)	0.0014 (15)	0.0045 (16)	0.0070 (16)
C42	0.027 (2)	0.0185 (18)	0.030 (2)	−0.0011 (14)	0.0014 (15)	0.0083 (15)
C43	0.0218 (18)	0.025 (2)	0.031 (2)	0.0027 (14)	0.0038 (15)	0.0092 (16)
C44	0.028 (2)	0.030 (2)	0.034 (2)	0.0033 (15)	0.0036 (17)	0.0103 (18)
N5	0.0271 (17)	0.0324 (18)	0.0318 (18)	0.0016 (13)	0.0019 (14)	0.0119 (15)
C51	0.029 (2)	0.038 (2)	0.030 (2)	0.0014 (16)	0.0066 (16)	0.0094 (17)
C52	0.032 (2)	0.050 (3)	0.040 (2)	0.0007 (18)	0.0024 (19)	0.014 (2)
C53	0.037 (2)	0.077 (4)	0.042 (3)	0.009 (2)	0.004 (2)	0.025 (3)
C54	0.049 (3)	0.080 (4)	0.048 (3)	0.021 (3)	0.010 (2)	0.039 (3)
C55	0.064 (3)	0.057 (3)	0.060 (3)	0.013 (2)	0.022 (3)	0.036 (3)
C56	0.041 (2)	0.046 (3)	0.045 (3)	0.0027 (19)	0.011 (2)	0.019 (2)
C57	0.0241 (19)	0.039 (2)	0.031 (2)	0.0008 (16)	0.0030 (15)	0.0114 (18)
C58	0.050 (3)	0.045 (3)	0.038 (2)	0.016 (2)	0.008 (2)	0.013 (2)
N6	0.0242 (16)	0.0269 (17)	0.0293 (17)	0.0012 (13)	0.0019 (13)	0.0049 (14)
C61	0.0224 (19)	0.041 (2)	0.030 (2)	0.0033 (16)	0.0005 (15)	0.0112 (18)
C62	0.031 (2)	0.038 (2)	0.033 (2)	0.0017 (16)	0.0045 (16)	0.0122 (18)
C63	0.035 (2)	0.042 (2)	0.037 (2)	0.0034 (18)	−0.0020 (18)	0.0114 (19)
C64	0.040 (2)	0.054 (3)	0.032 (2)	0.005 (2)	0.0087 (18)	0.003 (2)
C65	0.041 (3)	0.064 (3)	0.036 (2)	−0.003 (2)	0.013 (2)	0.019 (2)
C66	0.035 (2)	0.041 (2)	0.039 (2)	−0.0032 (18)	0.0013 (18)	0.014 (2)
C67	0.032 (2)	0.039 (2)	0.033 (2)	0.0056 (17)	0.0028 (17)	0.0132 (18)
C68	0.033 (2)	0.066 (3)	0.039 (2)	0.007 (2)	0.0031 (19)	0.010 (2)
N7	0.0268 (17)	0.0302 (18)	0.0336 (18)	0.0019 (13)	0.0037 (14)	0.0111 (15)
C71	0.0274 (19)	0.031 (2)	0.031 (2)	0.0007 (15)	0.0036 (15)	0.0084 (17)
C72	0.035 (2)	0.036 (2)	0.043 (2)	0.0083 (17)	0.0128 (18)	0.0149 (19)
C73	0.047 (3)	0.045 (3)	0.036 (2)	0.002 (2)	0.012 (2)	0.011 (2)
C74	0.040 (2)	0.050 (3)	0.040 (2)	0.0008 (19)	0.0012 (19)	0.023 (2)
C75	0.048 (3)	0.037 (2)	0.046 (3)	0.0104 (19)	0.004 (2)	0.020 (2)
C76	0.033 (2)	0.038 (2)	0.035 (2)	0.0073 (17)	0.0040 (17)	0.0103 (18)
C77	0.027 (2)	0.037 (2)	0.033 (2)	0.0013 (16)	0.0034 (16)	0.0112 (18)
C78	0.051 (3)	0.039 (3)	0.042 (3)	−0.010 (2)	0.000 (2)	0.012 (2)
N8	0.0253 (17)	0.0313 (18)	0.0349 (18)	0.0003 (13)	0.0007 (14)	0.0131 (15)
C81	0.033 (2)	0.032 (2)	0.031 (2)	0.0017 (16)	0.0023 (16)	0.0119 (17)
C82	0.041 (2)	0.038 (2)	0.045 (3)	0.0026 (19)	0.001 (2)	0.004 (2)
C83	0.060 (3)	0.045 (3)	0.047 (3)	0.012 (2)	0.004 (2)	0.000 (2)
C84	0.072 (4)	0.041 (3)	0.045 (3)	0.001 (2)	−0.005 (2)	0.006 (2)
C85	0.052 (3)	0.046 (3)	0.056 (3)	−0.003 (2)	−0.016 (2)	0.006 (2)
C86	0.032 (2)	0.045 (3)	0.047 (3)	−0.0014 (18)	−0.0031 (19)	0.006 (2)
C87	0.0262 (19)	0.031 (2)	0.036 (2)	0.0041 (16)	0.0007 (16)	0.0144 (17)
C88	0.039 (2)	0.032 (2)	0.039 (2)	−0.0014 (17)	0.0037 (18)	0.0127 (18)
N9	0.0261 (17)	0.0283 (17)	0.0350 (18)	−0.0010 (13)	0.0015 (14)	0.0115 (14)
C91	0.026 (2)	0.033 (2)	0.037 (2)	−0.0005 (16)	0.0034 (16)	0.0142 (18)
C92	0.041 (2)	0.041 (3)	0.038 (2)	0.0058 (19)	0.0007 (19)	0.010 (2)
C93	0.054 (3)	0.054 (3)	0.044 (3)	0.015 (2)	0.000 (2)	0.017 (2)
C94	0.059 (3)	0.055 (3)	0.038 (3)	0.002 (2)	−0.003 (2)	0.009 (2)
C95	0.041 (3)	0.047 (3)	0.047 (3)	0.006 (2)	0.006 (2)	−0.001 (2)
C96	0.030 (2)	0.037 (2)	0.042 (2)	0.0043 (17)	0.0023 (18)	0.0075 (19)
C97	0.0224 (19)	0.033 (2)	0.036 (2)	0.0048 (15)	0.0044 (15)	0.0144 (17)
C98	0.0264 (19)	0.030 (2)	0.042 (2)	−0.0022 (15)	0.0045 (17)	0.0125 (18)
N10	0.0267 (17)	0.0280 (18)	0.0320 (18)	0.0009 (13)	0.0029 (13)	0.0103 (14)
C101	0.033 (2)	0.030 (2)	0.037 (2)	0.0036 (16)	0.0064 (17)	0.0124 (18)
C102	0.036 (2)	0.041 (3)	0.057 (3)	0.0024 (19)	0.007 (2)	0.001 (2)
C103	0.055 (3)	0.049 (3)	0.050 (3)	0.000 (2)	0.000 (2)	0.000 (2)
C104	0.074 (4)	0.039 (3)	0.034 (2)	0.005 (2)	0.011 (2)	0.001 (2)
C105	0.059 (3)	0.054 (3)	0.047 (3)	0.011 (2)	0.026 (2)	0.010 (2)
C106	0.035 (2)	0.045 (3)	0.043 (3)	0.0019 (19)	0.0078 (19)	0.008 (2)
C107	0.0270 (19)	0.028 (2)	0.034 (2)	−0.0026 (15)	0.0042 (16)	0.0097 (17)
C108	0.039 (2)	0.036 (2)	0.039 (2)	0.0032 (17)	0.0015 (18)	0.0143 (19)
N11	0.0274 (17)	0.0300 (18)	0.0295 (17)	0.0005 (13)	0.0011 (13)	0.0095 (14)
C111	0.032 (2)	0.037 (2)	0.030 (2)	−0.0040 (17)	0.0057 (17)	0.0093 (18)
C112	0.035 (2)	0.048 (3)	0.038 (2)	0.0011 (18)	0.0057 (18)	0.018 (2)
C113	0.044 (2)	0.032 (2)	0.042 (3)	−0.0044 (18)	0.009 (2)	0.0069 (19)
C114	0.045 (3)	0.042 (3)	0.032 (2)	−0.0092 (19)	0.0053 (19)	0.0018 (19)
C115	0.042 (3)	0.055 (3)	0.039 (3)	0.003 (2)	0.003 (2)	0.014 (2)
C116	0.042 (2)	0.037 (2)	0.038 (2)	0.0011 (19)	0.0085 (19)	0.009 (2)
C117	0.034 (2)	0.051 (3)	0.031 (2)	−0.0120 (19)	0.0035 (17)	0.0115 (19)
C118	0.038 (3)	0.068 (3)	0.047 (3)	0.002 (2)	0.003 (2)	0.013 (2)
N12	0.0240 (17)	0.0291 (17)	0.0365 (18)	0.0036 (13)	0.0040 (14)	0.0122 (14)
C121	0.033 (2)	0.030 (2)	0.038 (2)	0.0060 (17)	−0.0002 (18)	0.0091 (18)
C122	0.048 (3)	0.047 (3)	0.041 (3)	0.000 (2)	0.010 (2)	0.015 (2)
C123	0.059 (3)	0.074 (4)	0.049 (3)	0.006 (3)	0.011 (3)	0.030 (3)
C124	0.059 (3)	0.081 (4)	0.038 (3)	0.019 (3)	0.007 (2)	0.017 (3)
C125	0.056 (3)	0.062 (3)	0.040 (3)	0.012 (3)	−0.006 (2)	−0.001 (2)
C126	0.036 (2)	0.039 (2)	0.047 (3)	0.0040 (18)	−0.0054 (19)	0.003 (2)
C127	0.0212 (18)	0.028 (2)	0.039 (2)	−0.0012 (14)	0.0005 (16)	0.0107 (17)
C128	0.028 (2)	0.033 (2)	0.052 (3)	0.0049 (16)	0.0050 (18)	0.0171 (19)
O1	0.095 (3)	0.065 (3)	0.073 (3)	0.004 (2)	−0.004 (3)	−0.006 (2)
C1	0.124 (7)	0.132 (7)	0.082 (5)	0.002 (6)	0.036 (5)	0.040 (5)
O2	0.084 (3)	0.071 (3)	0.085 (3)	−0.022 (2)	0.024 (3)	−0.005 (2)
C2	0.149 (8)	0.121 (7)	0.095 (6)	0.027 (6)	0.021 (6)	0.060 (6)

Geometric parameters (Å, º)

O12—C11	1.259 (4)	N8—C87	1.499 (5)
O11—C11	1.261 (5)	N8—H8A	0.91
O13—C14	1.265 (5)	N8—H8B	0.91
O14—C14	1.249 (5)	N8—H8C	0.91
O15—C12	1.420 (4)	C81—C86	1.387 (6)
O15—H15	0.84	C81—C82	1.397 (6)
O16—C13	1.424 (5)	C81—C87	1.502 (6)
O16—H16	0.84	C82—C83	1.390 (6)
C11—C12	1.534 (5)	C82—H82	0.95
C12—C13	1.525 (5)	C83—C84	1.394 (7)
C12—H12D	1.00	C83—H83	0.95
C13—C14	1.535 (5)	C84—C85	1.374 (7)
C13—H13A	1.00	C84—H84	0.95
O21—C21	1.259 (5)	C85—C86	1.386 (7)
O22—C21	1.263 (5)	C85—H85	0.95
O23—C24	1.264 (5)	C86—H86	0.95
O24—C24	1.238 (5)	C87—C88	1.535 (6)
O25—C22	1.416 (4)	C87—H87	1.00
O25—H25	0.84	C88—H88A	0.98
O26—C23	1.426 (4)	C88—H88B	0.98
O26—H26	0.84	C88—H88C	0.98
C21—C22	1.543 (5)	N9—C97	1.511 (5)
C22—C23	1.519 (5)	N9—H9A	0.91
C22—H22A	1.00	N9—H9B	0.91
C23—C24	1.539 (5)	N9—H9C	0.91
C23—H23A	1.00	C91—C92	1.391 (6)
O31—C31	1.261 (5)	C91—C96	1.395 (6)
O32—C31	1.250 (5)	C91—C97	1.507 (6)
O33—C34	1.257 (5)	C92—C93	1.379 (7)
O34—C34	1.242 (5)	C92—H92	0.95
O35—C32	1.429 (4)	C93—C94	1.381 (7)
O35—H35	0.84	C93—H93	0.95
O36—C33	1.429 (5)	C94—C95	1.379 (7)
O36—H36	0.84	C94—H94	0.95
C31—C32	1.543 (5)	C95—C96	1.383 (6)
C32—C33	1.521 (5)	C95—H95	0.95
C32—H32A	1.00	C96—H96	0.95
C33—C34	1.542 (5)	C97—C98	1.522 (5)
C33—H33A	1.00	C97—H97	1.00
O41—C41	1.267 (5)	C98—H98A	0.98
O42—C41	1.257 (5)	C98—H98B	0.98
O43—C44	1.253 (5)	C98—H98C	0.98
O44—C44	1.231 (5)	N10—C107	1.496 (5)
O45—C42	1.417 (4)	N10—H10A	0.91
O45—H45	0.84	N10—H10B	0.91
O46—C43	1.426 (5)	N10—H10C	0.91
O46—H46	0.84	C101—C106	1.380 (6)
C41—C42	1.542 (5)	C101—C102	1.388 (6)
C42—C43	1.515 (5)	C101—C107	1.524 (5)
C42—H42A	1.00	C102—C103	1.396 (7)
C43—C44	1.533 (5)	C102—H102	0.95
C43—H43A	1.00	C103—C104	1.377 (7)
N5—C57	1.513 (5)	C103—H103	0.95
N5—H5A	0.91	C104—C105	1.378 (8)
N5—H5B	0.91	C104—H104	0.95
N5—H5C	0.91	C105—C106	1.391 (6)
C51—C56	1.393 (6)	C105—H105	0.95
C51—C52	1.395 (6)	C106—H106	0.95
C51—C57	1.514 (6)	C107—C108	1.523 (5)
C52—C53	1.385 (6)	C107—H107	1.00
C52—H52	0.95	C108—H10D	0.98
C53—C54	1.375 (8)	C108—H10E	0.98
C53—H53	0.95	C108—H10F	0.98
C54—C55	1.370 (8)	N11—C117	1.512 (5)
C54—H54	0.95	N11—H11A	0.91
C55—C56	1.401 (7)	N11—H11B	0.91
C55—H55	0.95	N11—H11C	0.91
C56—H56	0.95	C111—C112	1.394 (6)
C57—C58	1.516 (6)	C111—C116	1.395 (6)
C57—H57	1.00	C111—C117	1.508 (6)
C58—H58A	0.98	C112—C113	1.379 (6)
C58—H58B	0.98	C112—H112	0.95
C58—H58C	0.98	C113—C114	1.376 (7)
N6—C67	1.501 (5)	C113—H113	0.95
N6—H6A	0.91	C114—C115	1.387 (7)
N6—H6B	0.91	C114—H114	0.95
N6—H6C	0.91	C115—C116	1.380 (6)
C61—C62	1.385 (6)	C115—H115	0.95
C61—C66	1.404 (6)	C116—H116	0.95
C61—C67	1.505 (5)	C117—C118	1.463 (6)
C62—C63	1.393 (6)	C117—H117	1.00
C62—H62	0.95	C118—H11D	0.98
C63—C64	1.385 (6)	C118—H11E	0.98
C63—H63	0.95	C118—H11F	0.98
C64—C65	1.384 (7)	N12—C127	1.506 (5)
C64—H64	0.95	N12—H12A	0.91
C65—C66	1.393 (6)	N12—H12B	0.91
C65—H65	0.95	N12—H12C	0.91
C66—H66	0.95	C121—C122	1.391 (6)
C67—C68	1.504 (6)	C121—C126	1.402 (6)
C67—H67	1.00	C121—C127	1.511 (6)
C68—H68A	0.98	C122—C123	1.392 (7)
C68—H68B	0.98	C122—H122	0.95
C68—H68C	0.98	C123—C124	1.368 (8)
N7—C77	1.503 (5)	C123—H123	0.95
N7—H7A	0.91	C124—C125	1.381 (8)
N7—H7B	0.91	C124—H124	0.95
N7—H7C	0.91	C125—C126	1.381 (7)
C71—C72	1.393 (5)	C125—H125	0.95
C71—C76	1.399 (6)	C126—H126	0.95
C71—C77	1.511 (6)	C127—C128	1.516 (5)
C72—C73	1.378 (6)	C127—H127	1.00
C72—H72	0.95	C128—H12E	0.98
C73—C74	1.380 (6)	C128—H12F	0.98
C73—H73	0.95	C128—H12G	0.98
C74—C75	1.378 (6)	O1—C1	1.304 (8)
C74—H74	0.95	O1—H1	0.84
C75—C76	1.386 (6)	C1—H1A	0.98
C75—H75	0.95	C1—H1B	0.98
C76—H76	0.95	C1—H1C	0.98
C77—C78	1.509 (6)	O2—C2	1.380 (11)
C77—H77	1.00	O2—H2	0.84
C78—H78A	0.98	C2—H2A	0.98
C78—H78B	0.98	C2—H2B	0.98
C78—H78C	0.98	C2—H2C	0.98
C12—O15—H15	109.5	C87—N8—H8C	109.5
C13—O16—H16	109.5	H8A—N8—H8C	109.5
O12—C11—O11	124.2 (3)	H8B—N8—H8C	109.5
O12—C11—C12	118.4 (3)	C86—C81—C82	119.0 (4)
O11—C11—C12	117.4 (3)	C86—C81—C87	118.8 (3)
O15—C12—C13	111.3 (3)	C82—C81—C87	122.1 (4)
O15—C12—C11	111.2 (3)	C83—C82—C81	120.1 (4)
C13—C12—C11	111.2 (3)	C83—C82—H82	119.9
O15—C12—H12D	107.6	C81—C82—H82	119.9
C13—C12—H12D	107.6	C82—C83—C84	120.0 (4)
C11—C12—H12D	107.6	C82—C83—H83	120.0
O16—C13—C12	107.7 (3)	C84—C83—H83	120.0
O16—C13—C14	112.4 (3)	C85—C84—C83	119.9 (5)
C12—C13—C14	111.4 (3)	C85—C84—H84	120.0
O16—C13—H13A	108.4	C83—C84—H84	120.0
C12—C13—H13A	108.4	C84—C85—C86	120.2 (5)
C14—C13—H13A	108.4	C84—C85—H85	119.9
O14—C14—O13	125.6 (4)	C86—C85—H85	119.9
O14—C14—C13	117.6 (3)	C85—C86—C81	120.7 (4)
O13—C14—C13	116.8 (4)	C85—C86—H86	119.6
C22—O25—H25	109.5	C81—C86—H86	119.6
C23—O26—H26	109.5	N8—C87—C81	112.1 (3)
O21—C21—O22	124.7 (3)	N8—C87—C88	109.2 (3)
O21—C21—C22	117.3 (3)	C81—C87—C88	112.0 (3)
O22—C21—C22	117.9 (3)	N8—C87—H87	107.8
O25—C22—C23	111.6 (3)	C81—C87—H87	107.8
O25—C22—C21	112.1 (3)	C88—C87—H87	107.8
C23—C22—C21	110.6 (3)	C87—C88—H88A	109.5
O25—C22—H22A	107.5	C87—C88—H88B	109.5
C23—C22—H22A	107.5	H88A—C88—H88B	109.5
C21—C22—H22A	107.5	C87—C88—H88C	109.5
O26—C23—C22	108.3 (3)	H88A—C88—H88C	109.5
O26—C23—C24	112.3 (3)	H88B—C88—H88C	109.5
C22—C23—C24	111.3 (3)	C97—N9—H9A	109.5
O26—C23—H23A	108.3	C97—N9—H9B	109.5
C22—C23—H23A	108.3	H9A—N9—H9B	109.5
C24—C23—H23A	108.3	C97—N9—H9C	109.5
O24—C24—O23	124.8 (4)	H9A—N9—H9C	109.5
O24—C24—C23	117.5 (3)	H9B—N9—H9C	109.5
O23—C24—C23	117.6 (3)	C92—C91—C96	117.6 (4)
C32—O35—H35	109.5	C92—C91—C97	123.2 (4)
C33—O36—H36	109.5	C96—C91—C97	119.0 (3)
O32—C31—O31	125.0 (3)	C93—C92—C91	121.3 (4)
O32—C31—C32	118.4 (3)	C93—C92—H92	119.3
O31—C31—C32	116.6 (3)	C91—C92—H92	119.3
O35—C32—C33	111.2 (3)	C92—C93—C94	120.1 (5)
O35—C32—C31	110.9 (3)	C92—C93—H93	120.0
C33—C32—C31	111.3 (3)	C94—C93—H93	120.0
O35—C32—H32A	107.7	C95—C94—C93	119.7 (4)
C33—C32—H32A	107.7	C95—C94—H94	120.2
C31—C32—H32A	107.7	C93—C94—H94	120.2
O36—C33—C32	107.9 (3)	C94—C95—C96	120.1 (4)
O36—C33—C34	111.8 (3)	C94—C95—H95	120.0
C32—C33—C34	110.9 (3)	C96—C95—H95	120.0
O36—C33—H33A	108.7	C95—C96—C91	121.1 (4)
C32—C33—H33A	108.7	C95—C96—H96	119.5
C34—C33—H33A	108.7	C91—C96—H96	119.5
O34—C34—O33	125.4 (4)	C91—C97—N9	111.4 (3)
O34—C34—C33	118.0 (4)	C91—C97—C98	111.2 (3)
O33—C34—C33	116.6 (3)	N9—C97—C98	108.5 (3)
C42—O45—H45	109.5	C91—C97—H97	108.6
C43—O46—H46	109.5	N9—C97—H97	108.6
O42—C41—O41	124.3 (3)	C98—C97—H97	108.6
O42—C41—C42	118.3 (3)	C97—C98—H98A	109.5
O41—C41—C42	117.3 (3)	C97—C98—H98B	109.5
O45—C42—C43	112.0 (3)	H98A—C98—H98B	109.5
O45—C42—C41	111.9 (3)	C97—C98—H98C	109.5
C43—C42—C41	110.9 (3)	H98A—C98—H98C	109.5
O45—C42—H42A	107.3	H98B—C98—H98C	109.5
C43—C42—H42A	107.3	C107—N10—H10A	109.5
C41—C42—H42A	107.3	C107—N10—H10B	109.5
O46—C43—C42	107.9 (3)	H10A—N10—H10B	109.5
O46—C43—C44	112.9 (3)	C107—N10—H10C	109.5
C42—C43—C44	111.5 (3)	H10A—N10—H10C	109.5
O46—C43—H43A	108.1	H10B—N10—H10C	109.5
C42—C43—H43A	108.1	C106—C101—C102	119.4 (4)
C44—C43—H43A	108.1	C106—C101—C107	118.8 (4)
O44—C44—O43	124.1 (4)	C102—C101—C107	121.6 (4)
O44—C44—C43	117.8 (4)	C101—C102—C103	119.7 (4)
O43—C44—C43	118.2 (3)	C101—C102—H102	120.1
C57—N5—H5A	109.5	C103—C102—H102	120.1
C57—N5—H5B	109.5	C104—C103—C102	120.6 (5)
H5A—N5—H5B	109.5	C104—C103—H103	119.7
C57—N5—H5C	109.5	C102—C103—H103	119.7
H5A—N5—H5C	109.5	C103—C104—C105	119.5 (4)
H5B—N5—H5C	109.5	C103—C104—H104	120.2
C56—C51—C52	118.2 (4)	C105—C104—H104	120.2
C56—C51—C57	119.4 (4)	C104—C105—C106	120.2 (4)
C52—C51—C57	122.4 (4)	C104—C105—H105	119.9
C53—C52—C51	121.3 (4)	C106—C105—H105	119.9
C53—C52—H52	119.3	C101—C106—C105	120.5 (4)
C51—C52—H52	119.3	C101—C106—H106	119.7
C54—C53—C52	119.6 (5)	C105—C106—H106	119.7
C54—C53—H53	120.2	N10—C107—C108	110.1 (3)
C52—C53—H53	120.2	N10—C107—C101	111.3 (3)
C55—C54—C53	120.5 (4)	C108—C107—C101	111.8 (3)
C55—C54—H54	119.8	N10—C107—H107	107.9
C53—C54—H54	119.8	C108—C107—H107	107.9
C54—C55—C56	120.3 (5)	C101—C107—H107	107.9
C54—C55—H55	119.8	C107—C108—H10D	109.5
C56—C55—H55	119.8	C107—C108—H10E	109.5
C51—C56—C55	120.1 (5)	H10D—C108—H10E	109.5
C51—C56—H56	120.0	C107—C108—H10F	109.5
C55—C56—H56	120.0	H10D—C108—H10F	109.5
N5—C57—C51	111.5 (3)	H10E—C108—H10F	109.5
N5—C57—C58	108.3 (3)	C117—N11—H11A	109.5
C51—C57—C58	113.9 (3)	C117—N11—H11B	109.5
N5—C57—H57	107.6	H11A—N11—H11B	109.5
C51—C57—H57	107.6	C117—N11—H11C	109.5
C58—C57—H57	107.6	H11A—N11—H11C	109.5
C57—C58—H58A	109.5	H11B—N11—H11C	109.5
C57—C58—H58B	109.5	C112—C111—C116	118.4 (4)
H58A—C58—H58B	109.5	C112—C111—C117	122.9 (4)
C57—C58—H58C	109.5	C116—C111—C117	118.7 (4)
H58A—C58—H58C	109.5	C113—C112—C111	121.1 (4)
H58B—C58—H58C	109.5	C113—C112—H112	119.5
C67—N6—H6A	109.5	C111—C112—H112	119.5
C67—N6—H6B	109.5	C114—C113—C112	120.2 (4)
H6A—N6—H6B	109.5	C114—C113—H113	119.9
C67—N6—H6C	109.5	C112—C113—H113	119.9
H6A—N6—H6C	109.5	C113—C114—C115	119.4 (4)
H6B—N6—H6C	109.5	C113—C114—H114	120.3
C62—C61—C66	118.8 (4)	C115—C114—H114	120.3
C62—C61—C67	121.9 (4)	C116—C115—C114	120.8 (4)
C66—C61—C67	119.3 (4)	C116—C115—H115	119.6
C61—C62—C63	121.1 (4)	C114—C115—H115	119.6
C61—C62—H62	119.4	C115—C116—C111	120.1 (4)
C63—C62—H62	119.4	C115—C116—H116	119.9
C64—C63—C62	119.5 (4)	C111—C116—H116	119.9
C64—C63—H63	120.3	C118—C117—C111	114.2 (4)
C62—C63—H63	120.3	C118—C117—N11	110.0 (4)
C65—C64—C63	120.4 (4)	C111—C117—N11	109.5 (3)
C65—C64—H64	119.8	C118—C117—H117	107.6
C63—C64—H64	119.8	C111—C117—H117	107.6
C64—C65—C66	120.0 (4)	N11—C117—H117	107.6
C64—C65—H65	120.0	C117—C118—H11D	109.5
C66—C65—H65	120.0	C117—C118—H11E	109.5
C65—C66—C61	120.2 (4)	H11D—C118—H11E	109.5
C65—C66—H66	119.9	C117—C118—H11F	109.5
C61—C66—H66	119.9	H11D—C118—H11F	109.5
N6—C67—C68	109.2 (3)	H11E—C118—H11F	109.5
N6—C67—C61	110.4 (3)	C127—N12—H12A	109.5
C68—C67—C61	113.9 (4)	C127—N12—H12B	109.5
N6—C67—H67	107.7	H12A—N12—H12B	109.5
C68—C67—H67	107.7	C127—N12—H12C	109.5
C61—C67—H67	107.7	H12A—N12—H12C	109.5
C67—C68—H68A	109.5	H12B—N12—H12C	109.5
C67—C68—H68B	109.5	C122—C121—C126	118.5 (4)
H68A—C68—H68B	109.5	C122—C121—C127	122.1 (4)
C67—C68—H68C	109.5	C126—C121—C127	119.2 (4)
H68A—C68—H68C	109.5	C121—C122—C123	120.6 (5)
H68B—C68—H68C	109.5	C121—C122—H122	119.7
C77—N7—H7A	109.5	C123—C122—H122	119.7
C77—N7—H7B	109.5	C124—C123—C122	119.9 (5)
H7A—N7—H7B	109.5	C124—C123—H123	120.0
C77—N7—H7C	109.5	C122—C123—H123	120.0
H7A—N7—H7C	109.5	C123—C124—C125	120.4 (5)
H7B—N7—H7C	109.5	C123—C124—H124	119.8
C72—C71—C76	118.2 (4)	C125—C124—H124	119.8
C72—C71—C77	122.8 (4)	C126—C125—C124	120.2 (5)
C76—C71—C77	119.0 (3)	C126—C125—H125	119.9
C73—C72—C71	120.6 (4)	C124—C125—H125	119.9
C73—C72—H72	119.7	C125—C126—C121	120.3 (5)
C71—C72—H72	119.7	C125—C126—H126	119.9
C72—C73—C74	120.8 (4)	C121—C126—H126	119.9
C72—C73—H73	119.6	N12—C127—C121	112.2 (3)
C74—C73—H73	119.6	N12—C127—C128	107.9 (3)
C75—C74—C73	119.5 (4)	C121—C127—C128	112.5 (3)
C75—C74—H74	120.3	N12—C127—H127	108.0
C73—C74—H74	120.3	C121—C127—H127	108.0
C74—C75—C76	120.3 (4)	C128—C127—H127	108.0
C74—C75—H75	119.9	C127—C128—H12E	109.5
C76—C75—H75	119.9	C127—C128—H12F	109.5
C75—C76—C71	120.6 (4)	H12E—C128—H12F	109.5
C75—C76—H76	119.7	C127—C128—H12G	109.5
C71—C76—H76	119.7	H12E—C128—H12G	109.5
N7—C77—C78	108.8 (3)	H12F—C128—H12G	109.5
N7—C77—C71	111.3 (3)	C1—O1—H1	109.5
C78—C77—C71	113.9 (3)	O1—C1—H1A	109.5
N7—C77—H77	107.5	O1—C1—H1B	109.5
C78—C77—H77	107.5	H1A—C1—H1B	109.5
C71—C77—H77	107.5	O1—C1—H1C	109.5
C77—C78—H78A	109.5	H1A—C1—H1C	109.5
C77—C78—H78B	109.5	H1B—C1—H1C	109.5
H78A—C78—H78B	109.5	C2—O2—H2	109.5
C77—C78—H78C	109.5	O2—C2—H2A	109.5
H78A—C78—H78C	109.5	O2—C2—H2B	109.5
H78B—C78—H78C	109.5	H2A—C2—H2B	109.5
C87—N8—H8A	109.5	O2—C2—H2C	109.5
C87—N8—H8B	109.5	H2A—C2—H2C	109.5
H8A—N8—H8B	109.5	H2B—C2—H2C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O15—H15···O12	0.84	2.37	2.661 (4)	101
O15—H15···O34^i	0.84	1.84	2.628 (4)	156
O16—H16···O21	0.84	1.90	2.722 (4)	167
O25—H25···O22	0.84	2.38	2.675 (4)	101
O25—H25···O44^ii	0.84	1.82	2.584 (4)	150
O26—H26···O11	0.84	1.89	2.712 (4)	168
O35—H35···O14	0.84	1.83	2.617 (4)	156
O36—H36···O41	0.84	1.91	2.741 (4)	171
O45—H45···O42	0.84	2.38	2.677 (4)	101
O45—H45···O24^iii	0.84	1.82	2.585 (4)	150
O46—H46···O31	0.84	1.88	2.711 (4)	171
N5—H5A···O23^iii	0.91	1.98	2.885 (4)	171
N5—H5B···O22^iv	0.91	1.99	2.882 (4)	168
N5—H5C···O46	0.91	2.00	2.902 (4)	173
N6—H6A···O45	0.91	2.10	2.973 (4)	161
N6—H6B···O22^iv	0.91	1.96	2.858 (4)	169
N6—H6C···O11^iii	0.91	1.89	2.768 (4)	160
N7—H7A···O43^v	0.91	2.01	2.898 (4)	167
N7—H7B···O42	0.91	1.95	2.859 (4)	173
N7—H7C···O26^iii	0.91	2.00	2.906 (4)	178
N8—H8A···O33^i	0.91	1.93	2.822 (4)	168
N8—H8B···O16	0.91	2.03	2.912 (4)	163
N8—H8C···O32	0.91	1.96	2.869 (4)	175
N9—H9A···O41^i	0.91	1.93	2.832 (4)	169
N9—H9B···O32	0.91	2.00	2.891 (4)	167
N9—H9C···O15	0.91	1.92	2.825 (4)	174
N10—H10A···O36	0.91	2.04	2.920 (4)	162
N10—H10B···O12^v	0.91	1.95	2.852 (4)	173
N10—H10C···O13	0.91	1.93	2.819 (4)	165
N11—H11A···O42^vi	0.91	1.96	2.863 (4)	171
N11—H11B···O31^ii	0.91	1.91	2.781 (4)	160
N11—H11C···O25	0.91	2.03	2.918 (4)	163
N12—H12A···O21	0.91	1.93	2.832 (4)	170
N12—H12B···O12^v	0.91	2.00	2.906 (4)	172
N12—H12C···O35	0.91	1.94	2.844 (4)	177
O1—H1···O23	0.84	1.90	2.730 (5)	170
O2—H2···O43	0.84	1.97	2.791 (5)	164

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

 

Footnotes

¹Supplementary data for this paper are available from the IUCr electronic archives (Reference: BM5020 ). Services for accessing these data are described at the back of the journal.