Structural study of six cyclo­alkyl­ammonium cinnamate salt structures featuring one-dimensional columns and two-dimensional hydrogen-bonded networks

Six ammonium carboxyl­ate salts, namely cyclo­pentyl­ammonium cinnamate, C₅H₁₂N⁺·C₉H₇O₂⁻, (I), cyclo­hexyl­ammonium cinnamate, C₆H₁₄N⁺·C₉H₇O₂⁻, (II), cyclo­heptyl­ammonium cinnamate form I, C₇H₁₆N⁺·C₉H₇O₂⁻, (IIIa), and form II, (IIIb), cyclo­octylammonium cinnamate, C₈H₁₈N⁺·C₉H₇O₂⁻, (IV), and cyclo­dodecyl­ammonium cinnamate, C₁₂H₂₆N⁺·C₉H₇O₂⁻, (V), are reported. Salts (II)–(V) all have a 1:1 ratio of cation to anion and feature three N⁺—H...O⁻ hydrogen bonds forming one-dimensional hydrogen-bonded columns consisting of repeat­ing R₄³(10) rings, while salt (I) has a two-dimensional network made up of alternating R₄⁴(12) and R⁶₈(20) rings. Salt (III) consists of two polymorphic forms, viz. form I having Z′ = 1 and form II with Z′ = 2. The latter polymorph has disorder of the cyclo­heptane rings in the two cations, as well as whole-mol­ecule disorder of one of the cinnamate anions. A similar, but ordered, Z′ = 2 structure is seen in salt (IV).

S1. Comment

Understanding how to control the solid-state formation of molecules using a variety of intermolecular interactions is at the heart of crystal engineering (Tiekink et al., 2010). Supramolecular synthesis makes use especially of the hydrogen bond, as the most directional of the known intermolecular interactions (Aakeröy & Beatty, 2001). Concepts of crystal engineering have been applied in the synthesis of aminium carboxylate salts, of general formula (R–NH₃⁺).(R'–COO^-), to form hydrogen-bonded one-dimensional columns in the solid state (Lemmerer, 2008, 2011a,b,c; Nagahama et al., 2003; Odendal et al., 2010; Yuge et al., 2008)). The hydrogen bond used in these molecular salts is the robust charge-assisted N⁺—H···O^- interaction (Braga et al., 2000), and three such hydrogen bonds can be formed from the primary aminium cation to carboxylate anion. In the past, we have made one-dimensional columns using this type of hydrogen bond (Lemmerer et al., 2010) and the most commonly encountered consists of repeating R₄³(10) rings (Fig. 1), described using graph-set notation (Bernstein et al., 1995). The packing of columns is based on the close packing principle of bumps in hollows. Each individual column, when viewed down its length, resembles a cross, X, as the hydrogen-bonding functional groups point inward (centred at the centre of the cross), and the hydrocarbon parts point outward, and the latter then interdigitate as best as possible with neighbouring columns (X). The counter-cations are cycloalkylaminium cations with ring sizes ranging from three- to 12-membered. So far, the anion has been planar and the carboxylate functional groups coplanar with the hydrocarbon backbone. In this study, we want to observe if similar hydrogen-bonded rings and assemblies are found for molecules where the carboxylate functional groups are extended further out from the ring, yet still predominantly planar by using cinnamic acid. To this end, we synthesized and characterized, using single-crystal X-ray diffraction, six salts, namely cyclopentylaminium cinnamate, (I), cyclohexylaminium cinnamate, (II), cycloheptylaminium cinnamate form I, (IIIa), cycloheptylaminium cinnamate form II, (IIIb), cyclooctylaminium cinnamate, (IV), and cyclododecylaminium cinnamate, (V). These six aminium carboxylate salts were all prepared in an identical manner. A 1:1 stoichiometric ratio of amine-to-acid was dissolved in methanol and crystals grown by slow evaporation at room temperature. Since the hydrogen-bonded interactions are central to this study, the H atoms on the aminium group are all labelled consistently in order to make comparisons of the six structures easier. H1A on the aminium group is always trans to the methine H10 atom on the cyclic hydrocarbon ring and forms a symmetry-independent hydrogen bond to O1 or O2 on the benzoate anion. Similarly, H2A is trans to the methine H atom, and forms a symmetry-independent hydrogen bond to O3 or O4 for those salts with Z' = 2. H1B and H1C are then labelled clockwise relative to H1A, viewed from N1 to the C atom of the hydrocarbon ring, and similarly for H2B and H2C. For the cinnamate anion, O1 is anti to the double bond and O2 is syn, and similarly for O3 and O4.

The molecular structure and atom-numbering scheme of the asymmetric unit of the 1:1 salt cyclopentylaminium cinnamate, (I), are shown in Fig. 2. The asymmetric unit consists of one cyclopentylaminium cation and one cinnamate anion, both on general positions. The cyclopentyl ring has an envelope conformation. The aminium group forms three charge-assisted hydrogen bonds to form two types of rings: (i) an R₄⁴(12) ring, consisting of two aminium cations and two carboxylate anions, involving atoms O1 and O2, and (ii) a second, larger R⁶₈(20) ring, using four cations, two anions using both O atoms and two anions using only one O atom (Fig. 3a). This hydrogen-bonded pattern leads to a two-dimensional network parallel to the ab plane, which has the hydrocarbon ends of the ions approximately perpendicular to the hydrogen-bonded layers. Adjacent layers are interdigitated through the aromatic rings of the cinnamate anions (Fig. 3b).

The molecular structure and atom-numbering scheme of the asymmetric unit of the 1:1 salt cyclohexylaminium cinnamate, (II), are shown in Fig. 4. The asymmetric unit consists of one cyclohexylaminium cation and one cinnamate anion, both on general positions. The cyclohexyl ring has a chair conformation. The aminium group forms three charge-assisted hydrogen bonds to form a ring [graph-set notation R₄³(10)] consisting of two aminium cations and two carboxylate anions, one involving both atoms O1 and O2 and the second involving only atom O2 (see Fig. 5a). All three aminium H atoms are used to form the rings and atom O2 acts as a bifurcated hydrogen-bond acceptor and forms a symmetry-independent hydrogen bond to H1A. This hydrogen-bonded pattern has translational symmetry via a twofold screw axis along the crystallographic b axis inherent in the space group P2₁/n, leading to one-dimensional hydrogen-bonded columns. The columns pack closely by interdigitation of the cyclohexane and aromatic rings (Fig. 5b).

The molecular structure and atom-numbering scheme of the asymmetric unit of form I of the 1:1 salt cycloheptylaminium cinnamate, (IIIa), are shown in Fig. 6. The asymmetric unit consists of one cycloheptylaminium cation and one cinnamate anion, both on general positions. The cycloheptyl ring has a twist-boat conformation. The aminium group forms three charge-assisted hydrogen bonds to form a ring [graph-set notation R₄³(10)] consisting of two aminium cations and two carboxylate anions, one involving both atoms O1 and O2 and the second involving only atom O1, different to (II). All three aminium H atoms are used to form the rings and atom O1 acts as a bifurcated hydrogen-bond acceptor and forms a symmetry-independent hydrogen bond to H1A in this case. This hydrogen-bonded pattern has translational symmetry via a twofold screw axis along the crystallographic a axis inherent in the space group P2₁2₁2₁, and forms one-dimensional hydrogen-bonded columns. The columns pack closely by interdigitation of the cycloheptyl and aromatic rings (Fig. 7).

The molecular structure and atom-numbering scheme of the asymmetric unit of form II of the 1:1 salt cycloheptylaminium cinnamate, (IIIb), are shown in Fig. 8. The asymmetric unit consists of two cycloheptylaminium cations (labelled N1 and N2), and two cinnamate anions (labelled O1/O2 and O3/O4), all on general positions. Both N1 and N2 cations have two ring C atoms split over two positions, such that the cycloheptyl rings adopt one of two twist-chair conformations. The cinnamate anion O1/O2 features whole-molecule disorder. The second anion is completely ordered. In the descriptions of the hydrogen bonding, we will focus on the major parts of the disordered components. Both sets of cation/anion pairs form R₄³(10) rings as seen in (II), where the symmetry-independent hydrogen bonds from H1A and H2A are to O2 and O4, respectively. This leads to two symmetry-independent one-dimensional columns, running along the b axis, and which again interdigitate through the cycloheptyl and aromatic rings (Fig. 9).

The molecular structure and atom-numbering scheme of the asymmetric unit of the 1:1 salt cyclooctylaminium cinnamate, (IV), are shown in Fig. 10. The asymmetric unit consists of two cyclooctylaminium cations (labelled N1 and N2), and two cinnamate anions (labelled O1/O2 and O3/O4), all on general positions. Both N1 and N2 cations have boat–chair conformations. Both sets of cation/anion pairs form R₄³(10) rings as seen in (IIIb), where the symmetry-independent hydrogen bonds from H1A and H2A are to O2 and O4, respectively. This leads to two symmetry-independent one-dimensional columns, running along the b axis, and again interdigitate through the cyclooctyl and aromatic rings (Fig. 11).

The molecular structure and atom-numbering scheme of the asymmetric unit of the 1:1 salt cyclododecylaminium cinnamate, (V), are shown in Fig. 12. The asymmetric unit consists of one cycloheptylaminium cation and one cinnamate anion, both on general positions. The aminium group forms three charge-assisted hydrogen bonds to form a ring [graph-set notation R₄³(10)] consisting of two aminium cations and two carboxylate anions, one involving both atoms O1 and O2 and the second involving only atom O1, as seen in (IIIa). All three aminium H atoms are used to form the rings, and atom O1 acts as a bifurcated hydrogen-bond acceptor and forms a symmetry-independent hydrogen bond to H1A in this case. This hydrogen-bonded pattern has translational symmetry via a twofold screw axis along the crystallographic b axis inherent in the space group P2₁, and forms one-dimensional hydrogen-bonded columns. The columns back [pack?] closely by interdigitation of the cycloheptyl and aromatic rings (Fig. 13).

Related literature

For related literature, see: Aakeröy & Beatty, 2001; Bernstein et al. (1995); Braga et al. (2000); Flack & Bernardinelli (2000); Lemmerer (2008); Lemmerer et al., (2010); Lemmerer (2011a, 2011b, 2011c); Nagahama et al. (2003); Odendal et al. (2010); Tiekink et al. (2010); Yuge et al. (2008).

S2. Experimental

All chemicals were purchased from commercial sources and used as received. Crystals were grown by slow evaporation at ambient conditions of a methanol solution containing a 1:1 ratio of amine and acid. Detailed masses and volumes are as follows: for (I), cyclopentylamine (0.115 g, 1.35 mmol) and cinnamic acid (0.200 g, 1.35 mmol) in methanol (8 ml); for (II), cyclohexylamine (0.134 g, 1.35 mmol) and cinnamic acid (0.200 g, 1.35 mmol) in methanol (8 ml); for (IIIa), cycloheptylamine (0.153 g, 1.35 mmol) and cinnamic acid (0.200 g, 1.35 mmol) in methanol (8 ml); for (IIIb), cycloheptylamine (0.153 g, 1.35 mmol) and cinnamic acid (0.200 g, 1.35 mmol) dissolved in hot methanol (8 ml) using sonication for 2 min; for (IV), cyclooctylamine (0.172 g, 1.35 mmol) and cinnamic acid (0.200 g, 1.35 mmol) in methanol (8 ml); for (V), cyclododecylamine (0.248 g, 1.35 mmol) and cinnamic acid (0.200 g, 1.35 mmol) in methanol (8 ml).

S3. Refinement

For all compounds, the C-bound H atoms were geometrically placed [C—H bond lengths of 1.00 (methine CH), 0.99 (ethylene CH₂) and 0.95 Å (Ar—H)] and refined as riding with U_iso(H) = 1.2U_eq(C). The N-bound H atoms were located in the difference map and their coordinates allowed to refine freely, with U_iso(H) = 1.5U_eq(N).

The whole-molecule disorder of one of the cinnamate anions in (IIIb) was modelled by finding alternative positions for all the atoms in the molecule. The corresponding bonded distance and the one-angle nonbonded distances in the two disorder components were restrained to have similar values, subject to s.u. values of 0.005 and 0.01 Å, respectively. For the carboxylate groups, the bond lengths and angles were restrained to values of the second cinnamate anion, which was ordered. Refinement of the site occupancies gave values of 0.583 (5) and 0.417 (5). For the two cycloheptane cations, the disorder of the C12 and C15 atoms in cation N1, and of C28 and C31 in cation N2 was resolved by finding alternative positions for the two in the difference Fourier map, and were then refined anisotropically together with their site occupancy, such that the sum of the occupancies summed to one. Refinement of the site occupancies gave values of 0.835 (3) and 0.165 (3) for cation N1, and values of 0.616 (3) and 0.384 (3) for cation N2.

In (IIIa) and (V), the absolute structure was chosen arbitrarily, and refinement of the absolute structure parameter (Flack & Bernardinelli, 2000) led to values whose precision was too poor to enable conclusions to be drawn about the absolute structure, so the Friedel pairs of reflections were merged prior to the final refinements.

In (IV), the diffraction data have been cut off at a 2θ angle of 47° because of weak data above this angle.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures

	Fig. 1. The most common type of ladder formed by ammonium carboxylate salts.
	Fig. 2. A perspective view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. The dashed line indicates the symmetry-independent N^+—H···O^- hydrogen bond.
	Fig. 3. (a) View of the two-dimensional hydrogen-bonded layer formed by the R4^4(12) and R8^6(20) rings in (I). The hydrocarbon ring of the cation has been omitted for clarity. (b) The packing of the layers, interdigitated through the cinnamate anions. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 4. A perspective view of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. The dashed line indicates the symmetry-independent N^+—H···O^- hydrogen bond.
	Fig. 5. (a) The R4^3(10) rings forming a one-dimensional column in (II). (b) Packing diagram of the columns. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 6. A perspective view of (IIIa), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. The dashed line indicates the symmetry-independent N^+—H···O^- hydrogen bond.
	Fig. 7. Packing of the hydrogen-bonded columns in (IIIa), formed by repeating R4^3(10) rings. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 8. A perspective view of (IIIb), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. The dashed line indicates the symmetry-independent N^+—H···O^- hydrogen bond. Only the major parts of the disorder are shown, and C-bound H atoms have been omitted for clarity.
	Fig. 9. Packing of the two symmetry-independent hydrogen-bonded columns in (IIIb), formed by repeating R4^3(10) rings. Note the alternating pattern along the c axis of the two columns. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 10. A perspective view of (IV), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. The dashed line indicates the symmetry-independent N^+—H···O^- hydrogen bond. C-bound H atoms have been omitted for clarity.
	Fig. 11. Packing of the hydrogen-bonded columns in (IV), formed by repeating R4^3(10) rings. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 12. A perspective view of (V), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. The dashed line indicates the symmetry-independent N^+—H···O^- hydrogen bond.
	Fig. 13. Packing of the hydrogen-bonded columns in (V), formed by repeating R4^3(10) rings. H atoms not involved in hydrogen bonding have been omitted for clarity.

(I) cyclopentylaminium cinnamate

Crystal data

C5H12N^+·C9H7O2^−	F(000) = 1008
Mr = 233.3	Dx = 1.211 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3764 reflections
a = 8.2523 (3) Å	θ = 2.9–27.8°
b = 11.1475 (3) Å	µ = 0.08 mm^−1
c = 27.8170 (7) Å	T = 173 K
V = 2558.96 (13) Å^3	Block, colourless
Z = 8	0.55 × 0.4 × 0.1 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	2170 reflections with I > 2σ(I)
ω scans	Rint = 0.051
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 28°, θmin = 1.5°
Tmin = 0.957, Tmax = 0.992	h = −10→10
14051 measured reflections	k = −14→13
3092 independent reflections	l = −36→31

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0557P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.107	(Δ/σ)max = 0.004
S = 1.02	Δρmax = 0.21 e Å^−3
3092 reflections	Δρmin = −0.20 e Å^−3
163 parameters

Special details

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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
C1	0.16314 (16)	0.71801 (11)	0.31780 (4)	0.0234 (3)
C2	0.10164 (18)	0.60335 (12)	0.32449 (4)	0.0289 (3)
H2	0.1005	0.5691	0.3558	0.035*
C3	0.04205 (19)	0.53868 (12)	0.28602 (5)	0.0326 (3)
H3	0.0014	0.4599	0.291	0.039*
C4	0.04103 (19)	0.58768 (13)	0.24029 (4)	0.0342 (4)
H4	−0.002	0.5434	0.2141	0.041*
C5	0.1026 (2)	0.70061 (13)	0.23307 (5)	0.0357 (4)
H5	0.104	0.7341	0.2017	0.043*
C6	0.16251 (18)	0.76564 (12)	0.27150 (4)	0.0306 (3)
H6	0.2039	0.8441	0.2662	0.037*
C7	0.22545 (16)	0.79085 (11)	0.35776 (4)	0.0240 (3)
H7	0.2495	0.8723	0.3506	0.029*
C8	0.25204 (16)	0.75598 (11)	0.40266 (4)	0.0243 (3)
H8	0.2288	0.6753	0.4112	0.029*
C9	0.31679 (15)	0.83817 (11)	0.44020 (4)	0.0219 (3)
O1	0.36421 (11)	0.79116 (8)	0.47944 (3)	0.0275 (2)
O2	0.32445 (12)	0.94812 (7)	0.43152 (3)	0.0277 (2)
C10	0.21780 (16)	0.54661 (11)	0.55691 (4)	0.0235 (3)
H10	0.1373	0.4829	0.5653	0.028*
C11	0.38635 (17)	0.49326 (12)	0.55821 (4)	0.0290 (3)
H11A	0.4661	0.5475	0.5429	0.035*
H11B	0.3894	0.4145	0.5418	0.035*
C12	0.4194 (2)	0.48004 (12)	0.61204 (5)	0.0347 (4)
H12A	0.5365	0.4895	0.6189	0.042*
H12B	0.384	0.4003	0.6236	0.042*
C13	0.32135 (18)	0.57989 (14)	0.63636 (5)	0.0368 (4)
H13A	0.2496	0.5459	0.6614	0.044*
H13B	0.3947	0.639	0.6516	0.044*
C14	0.22164 (19)	0.63925 (13)	0.59706 (4)	0.0340 (3)
H14A	0.2735	0.7145	0.5861	0.041*
H14B	0.1108	0.6575	0.6086	0.041*
N1	0.17382 (15)	0.59947 (10)	0.50967 (4)	0.0221 (2)
H1A	0.244 (2)	0.6603 (13)	0.5014 (5)	0.033*
H1B	0.070 (2)	0.6355 (12)	0.5116 (5)	0.033*
H1C	0.1743 (18)	0.5423 (13)	0.4854 (5)	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0237 (7)	0.0241 (6)	0.0223 (6)	0.0036 (5)	−0.0014 (5)	−0.0033 (5)
C2	0.0349 (8)	0.0292 (7)	0.0228 (6)	−0.0013 (6)	−0.0017 (5)	−0.0016 (5)
C3	0.0367 (9)	0.0290 (7)	0.0321 (7)	−0.0052 (6)	−0.0001 (6)	−0.0064 (6)
C4	0.0366 (9)	0.0404 (8)	0.0257 (7)	0.0028 (7)	−0.0058 (6)	−0.0116 (6)
C5	0.0474 (10)	0.0391 (8)	0.0206 (6)	0.0042 (7)	−0.0053 (6)	−0.0004 (6)
C6	0.0395 (9)	0.0271 (7)	0.0253 (6)	0.0018 (6)	−0.0038 (6)	0.0011 (6)
C7	0.0267 (7)	0.0202 (6)	0.0252 (6)	0.0017 (5)	−0.0013 (5)	−0.0008 (5)
C8	0.0272 (7)	0.0203 (6)	0.0255 (6)	−0.0013 (5)	−0.0025 (5)	−0.0004 (5)
C9	0.0215 (7)	0.0240 (7)	0.0203 (6)	−0.0011 (5)	0.0024 (5)	−0.0014 (5)
O1	0.0316 (6)	0.0295 (5)	0.0214 (4)	−0.0060 (4)	−0.0051 (4)	0.0029 (4)
O2	0.0373 (6)	0.0218 (5)	0.0239 (4)	−0.0018 (4)	−0.0026 (4)	−0.0021 (4)
C10	0.0270 (7)	0.0248 (7)	0.0188 (6)	−0.0007 (6)	0.0018 (5)	0.0010 (5)
C11	0.0305 (8)	0.0302 (7)	0.0263 (7)	0.0054 (6)	0.0030 (6)	−0.0008 (6)
C12	0.0386 (9)	0.0359 (8)	0.0295 (7)	0.0025 (7)	−0.0048 (6)	0.0008 (6)
C13	0.0309 (9)	0.0544 (10)	0.0250 (7)	0.0034 (7)	−0.0016 (6)	−0.0074 (6)
C14	0.0417 (9)	0.0351 (8)	0.0252 (6)	0.0063 (7)	−0.0011 (6)	−0.0075 (6)
N1	0.0252 (6)	0.0216 (6)	0.0194 (5)	−0.0006 (5)	0.0013 (4)	−0.0022 (4)

Geometric parameters (Å, º)

C1—C2	1.3878 (18)	C10—N1	1.4850 (15)
C1—C6	1.3931 (17)	C10—C11	1.5132 (19)
C1—C7	1.4695 (17)	C10—C14	1.5216 (17)
C2—C3	1.3808 (18)	C10—H10	1
C2—H2	0.95	C11—C12	1.5292 (18)
C3—C4	1.3844 (18)	C11—H11A	0.99
C3—H3	0.95	C11—H11B	0.99
C4—C5	1.372 (2)	C12—C13	1.534 (2)
C4—H4	0.95	C12—H12A	0.99
C5—C6	1.3830 (19)	C12—H12B	0.99
C5—H5	0.95	C13—C14	1.5199 (19)
C6—H6	0.95	C13—H13A	0.99
C7—C8	1.3264 (17)	C13—H13B	0.99
C7—H7	0.95	C14—H14A	0.99
C8—C9	1.4884 (17)	C14—H14B	0.99
C8—H8	0.95	N1—H1A	0.921 (16)
C9—O2	1.2508 (14)	N1—H1B	0.949 (17)
C9—O1	1.2725 (14)	N1—H1C	0.928 (15)
C2—C1—C6	118.27 (11)	C14—C10—H10	109
C2—C1—C7	122.37 (11)	C10—C11—C12	103.04 (10)
C6—C1—C7	119.34 (11)	C10—C11—H11A	111.2
C3—C2—C1	120.48 (12)	C12—C11—H11A	111.2
C3—C2—H2	119.8	C10—C11—H11B	111.2
C1—C2—H2	119.8	C12—C11—H11B	111.2
C2—C3—C4	120.55 (13)	H11A—C11—H11B	109.1
C2—C3—H3	119.7	C11—C12—C13	105.53 (11)
C4—C3—H3	119.7	C11—C12—H12A	110.6
C5—C4—C3	119.61 (12)	C13—C12—H12A	110.6
C5—C4—H4	120.2	C11—C12—H12B	110.6
C3—C4—H4	120.2	C13—C12—H12B	110.6
C4—C5—C6	120.01 (12)	H12A—C12—H12B	108.8
C4—C5—H5	120	C14—C13—C12	106.53 (10)
C6—C5—H5	120	C14—C13—H13A	110.4
C5—C6—C1	121.07 (13)	C12—C13—H13A	110.4
C5—C6—H6	119.5	C14—C13—H13B	110.4
C1—C6—H6	119.5	C12—C13—H13B	110.4
C8—C7—C1	127.46 (12)	H13A—C13—H13B	108.6
C8—C7—H7	116.3	C13—C14—C10	104.11 (11)
C1—C7—H7	116.3	C13—C14—H14A	110.9
C7—C8—C9	122.66 (12)	C10—C14—H14A	110.9
C7—C8—H8	118.7	C13—C14—H14B	110.9
C9—C8—H8	118.7	C10—C14—H14B	110.9
O2—C9—O1	123.61 (11)	H14A—C14—H14B	109
O2—C9—C8	119.07 (10)	C10—N1—H1A	111.1 (9)
O1—C9—C8	117.30 (11)	C10—N1—H1B	109.9 (8)
N1—C10—C11	113.70 (10)	H1A—N1—H1B	105.7 (12)
N1—C10—C14	112.66 (10)	C10—N1—H1C	111.7 (9)
C11—C10—C14	103.30 (11)	H1A—N1—H1C	108.7 (12)
N1—C10—H10	109	H1B—N1—H1C	109.5 (12)
C11—C10—H10	109
C6—C1—C2—C3	0.2 (2)	C1—C7—C8—C9	179.61 (12)
C7—C1—C2—C3	179.02 (13)	C7—C8—C9—O2	10.8 (2)
C1—C2—C3—C4	−0.7 (2)	C7—C8—C9—O1	−168.01 (12)
C2—C3—C4—C5	1.2 (2)	N1—C10—C11—C12	164.01 (11)
C3—C4—C5—C6	−1.2 (2)	C14—C10—C11—C12	41.59 (13)
C4—C5—C6—C1	0.6 (2)	C10—C11—C12—C13	−29.09 (15)
C2—C1—C6—C5	−0.1 (2)	C11—C12—C13—C14	5.70 (16)
C7—C1—C6—C5	−179.00 (13)	C12—C13—C14—C10	19.80 (16)
C2—C1—C7—C8	9.4 (2)	N1—C10—C14—C13	−161.27 (12)
C6—C1—C7—C8	−171.81 (14)	C11—C10—C14—C13	−38.16 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.921 (16)	1.866 (16)	2.7824 (15)	172.4 (14)
N1—H1B···O1^i	0.949 (17)	1.900 (17)	2.8471 (15)	175.6 (12)
N1—H1C···O2^ii	0.928 (15)	1.830 (15)	2.7519 (13)	171.6 (13)

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

(II) cyclohexylaminium cinnamate

Crystal data

C6H14N^+·C9H7O2^−	F(000) = 536
Mr = 247.33	Dx = 1.186 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2560 reflections
a = 13.4992 (4) Å	θ = 3.2–24.8°
b = 6.4723 (2) Å	µ = 0.08 mm^−1
c = 16.7352 (5) Å	T = 173 K
β = 108.610 (2)°	Block, colourless
V = 1385.72 (7) Å^3	0.5 × 0.26 × 0.06 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	1957 reflections with I > 2σ(I)
ω scans	Rint = 0.134
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 28°, θmin = 1.7°
Tmin = 0.962, Tmax = 0.995	h = −16→17
14450 measured reflections	k = −8→8
3348 independent reflections	l = −22→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0841P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.174	(Δ/σ)max = 0.01
S = 0.99	Δρmax = 0.45 e Å^−3
3348 reflections	Δρmin = −0.19 e Å^−3
172 parameters

Special details

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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
C1	0.14249 (13)	0.5524 (3)	0.55372 (11)	0.0498 (4)
C2	0.16377 (16)	0.4458 (3)	0.62962 (12)	0.0656 (6)
H2	0.1899	0.3085	0.6339	0.079*
C3	0.14728 (19)	0.5378 (4)	0.69839 (14)	0.0801 (7)
H3	0.1621	0.4638	0.7499	0.096*
C4	0.10984 (19)	0.7341 (4)	0.69302 (16)	0.0842 (7)
H4	0.0975	0.7963	0.7404	0.101*
C5	0.08984 (18)	0.8424 (4)	0.61901 (17)	0.0808 (7)
H5	0.0645	0.9801	0.6153	0.097*
C6	0.10661 (16)	0.7507 (3)	0.54981 (13)	0.0642 (5)
H6	0.093	0.8267	0.4989	0.077*
C7	0.15793 (13)	0.4600 (3)	0.47784 (11)	0.0514 (5)
H7	0.1487	0.5497	0.4311	0.062*
C8	0.18225 (14)	0.2731 (3)	0.46787 (11)	0.0533 (5)
H8	0.1945	0.1838	0.5151	0.064*
C9	0.19322 (12)	0.1814 (3)	0.38900 (10)	0.0423 (4)
O1	0.19899 (11)	−0.00988 (18)	0.38811 (7)	0.0628 (4)
O2	0.19758 (10)	0.29665 (17)	0.32964 (7)	0.0524 (3)
C10	0.43583 (12)	0.2145 (2)	0.28991 (10)	0.0438 (4)
H10	0.4829	0.2015	0.2546	0.053*
C11	0.45480 (13)	0.4230 (2)	0.33263 (12)	0.0564 (5)
H11A	0.4054	0.4433	0.3648	0.068*
H11B	0.442	0.5331	0.2895	0.068*
C12	0.56642 (15)	0.4389 (3)	0.39204 (13)	0.0698 (6)
H12A	0.6155	0.4312	0.3591	0.084*
H12B	0.5764	0.5741	0.4212	0.084*
C13	0.59061 (15)	0.2670 (3)	0.45683 (13)	0.0623 (5)
H13A	0.6646	0.2768	0.4929	0.075*
H13B	0.5461	0.2823	0.4934	0.075*
C14	0.57139 (14)	0.0595 (3)	0.41441 (12)	0.0590 (5)
H14A	0.5834	−0.0499	0.4578	0.071*
H14B	0.6219	0.0381	0.3833	0.071*
C15	0.46079 (14)	0.0402 (2)	0.35346 (11)	0.0528 (5)
H15A	0.4532	−0.0936	0.3235	0.063*
H15B	0.4105	0.0423	0.3854	0.063*
N1	0.32587 (11)	0.1992 (2)	0.23339 (9)	0.0432 (4)
H1A	0.2772 (16)	0.221 (3)	0.2666 (13)	0.065*
H1B	0.3177 (15)	0.068 (3)	0.2093 (12)	0.065*
H1C	0.3120 (15)	0.310 (3)	0.1933 (13)	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0414 (9)	0.0636 (11)	0.0461 (10)	−0.0115 (7)	0.0164 (7)	−0.0147 (8)
C2	0.0708 (13)	0.0686 (12)	0.0605 (13)	−0.0054 (10)	0.0254 (10)	−0.0094 (10)
C3	0.0885 (17)	0.1058 (19)	0.0537 (12)	−0.0139 (13)	0.0333 (12)	−0.0118 (12)
C4	0.0746 (15)	0.118 (2)	0.0695 (15)	−0.0161 (13)	0.0364 (12)	−0.0452 (15)
C5	0.0709 (14)	0.0764 (14)	0.0965 (18)	−0.0022 (11)	0.0289 (13)	−0.0359 (14)
C6	0.0623 (12)	0.0657 (12)	0.0665 (13)	−0.0049 (9)	0.0233 (10)	−0.0100 (10)
C7	0.0473 (10)	0.0589 (11)	0.0483 (10)	−0.0036 (8)	0.0156 (8)	−0.0016 (8)
C8	0.0597 (11)	0.0537 (10)	0.0463 (10)	−0.0072 (8)	0.0164 (8)	−0.0034 (8)
C9	0.0399 (8)	0.0460 (9)	0.0390 (9)	−0.0029 (7)	0.0096 (7)	−0.0036 (7)
O1	0.0944 (11)	0.0470 (7)	0.0452 (7)	−0.0011 (6)	0.0198 (7)	−0.0017 (6)
O2	0.0626 (8)	0.0490 (7)	0.0496 (7)	0.0036 (5)	0.0232 (6)	0.0048 (6)
C10	0.0430 (9)	0.0479 (9)	0.0412 (9)	0.0024 (7)	0.0144 (7)	0.0037 (7)
C11	0.0532 (10)	0.0409 (9)	0.0649 (12)	−0.0045 (7)	0.0045 (9)	0.0049 (8)
C12	0.0566 (12)	0.0572 (11)	0.0798 (15)	−0.0157 (9)	−0.0004 (10)	0.0119 (10)
C13	0.0508 (11)	0.0692 (12)	0.0562 (11)	−0.0092 (8)	0.0020 (9)	0.0043 (10)
C14	0.0597 (11)	0.0598 (11)	0.0515 (11)	0.0091 (8)	0.0094 (9)	0.0139 (9)
C15	0.0635 (11)	0.0399 (9)	0.0481 (10)	−0.0001 (7)	0.0080 (8)	0.0029 (7)
N1	0.0485 (8)	0.0407 (7)	0.0380 (8)	0.0003 (6)	0.0106 (6)	−0.0007 (6)

Geometric parameters (Å, º)

C1—C6	1.366 (3)	C10—C15	1.513 (2)
C1—C2	1.393 (3)	C10—H10	1
C1—C7	1.478 (2)	C11—C12	1.521 (2)
C2—C3	1.376 (3)	C11—H11A	0.99
C2—H2	0.95	C11—H11B	0.99
C3—C4	1.360 (3)	C12—C13	1.515 (3)
C3—H3	0.95	C12—H12A	0.99
C4—C5	1.373 (3)	C12—H12B	0.99
C4—H4	0.95	C13—C14	1.502 (2)
C5—C6	1.382 (3)	C13—H13A	0.99
C5—H5	0.95	C13—H13B	0.99
C6—H6	0.95	C14—C15	1.521 (2)
C7—C8	1.278 (2)	C14—H14A	0.99
C7—H7	0.95	C14—H14B	0.99
C8—C9	1.497 (2)	C15—H15A	0.99
C8—H8	0.95	C15—H15B	0.99
C9—O1	1.2408 (19)	N1—H1A	1.00 (2)
C9—O2	1.2587 (19)	N1—H1B	0.93 (2)
C10—N1	1.487 (2)	N1—H1C	0.96 (2)
C10—C11	1.510 (2)
C6—C1—C2	118.45 (17)	C12—C11—H11A	109.5
C6—C1—C7	118.98 (18)	C10—C11—H11B	109.5
C2—C1—C7	122.58 (16)	C12—C11—H11B	109.5
C3—C2—C1	120.5 (2)	H11A—C11—H11B	108.1
C3—C2—H2	119.8	C13—C12—C11	111.14 (15)
C1—C2—H2	119.8	C13—C12—H12A	109.4
C4—C3—C2	120.4 (2)	C11—C12—H12A	109.4
C4—C3—H3	119.8	C13—C12—H12B	109.4
C2—C3—H3	119.8	C11—C12—H12B	109.4
C3—C4—C5	119.9 (2)	H12A—C12—H12B	108
C3—C4—H4	120	C14—C13—C12	110.68 (16)
C5—C4—H4	120.1	C14—C13—H13A	109.5
C4—C5—C6	120.0 (2)	C12—C13—H13A	109.5
C4—C5—H5	120	C14—C13—H13B	109.5
C6—C5—H5	120	C12—C13—H13B	109.5
C1—C6—C5	120.9 (2)	H13A—C13—H13B	108.1
C1—C6—H6	119.6	C13—C14—C15	112.02 (14)
C5—C6—H6	119.6	C13—C14—H14A	109.2
C8—C7—C1	127.45 (18)	C15—C14—H14A	109.2
C8—C7—H7	116.3	C13—C14—H14B	109.2
C1—C7—H7	116.3	C15—C14—H14B	109.2
C7—C8—C9	126.32 (18)	H14A—C14—H14B	107.9
C7—C8—H8	116.8	C10—C15—C14	111.16 (14)
C9—C8—H8	116.8	C10—C15—H15A	109.4
O1—C9—O2	124.25 (15)	C14—C15—H15A	109.4
O1—C9—C8	115.50 (15)	C10—C15—H15B	109.4
O2—C9—C8	120.23 (15)	C14—C15—H15B	109.4
N1—C10—C11	110.16 (13)	H15A—C15—H15B	108
N1—C10—C15	110.52 (13)	C10—N1—H1A	109.7 (12)
C11—C10—C15	111.56 (13)	C10—N1—H1B	107.0 (12)
N1—C10—H10	108.2	H1A—N1—H1B	111.4 (16)
C11—C10—H10	108.2	C10—N1—H1C	109.1 (12)
C15—C10—H10	108.2	H1A—N1—H1C	105.5 (15)
C10—C11—C12	110.65 (14)	H1B—N1—H1C	114.1 (16)
C10—C11—H11A	109.5
C6—C1—C2—C3	1.0 (3)	C7—C8—C9—O1	−167.67 (18)
C7—C1—C2—C3	−179.43 (18)	C7—C8—C9—O2	13.3 (3)
C1—C2—C3—C4	0.1 (3)	N1—C10—C11—C12	178.81 (15)
C2—C3—C4—C5	−1.0 (4)	C15—C10—C11—C12	55.7 (2)
C3—C4—C5—C6	0.8 (4)	C10—C11—C12—C13	−56.7 (2)
C2—C1—C6—C5	−1.2 (3)	C11—C12—C13—C14	56.4 (2)
C7—C1—C6—C5	179.20 (17)	C12—C13—C14—C15	−55.3 (2)
C4—C5—C6—C1	0.4 (3)	N1—C10—C15—C14	−177.29 (14)
C6—C1—C7—C8	−173.66 (18)	C11—C10—C15—C14	−54.4 (2)
C2—C1—C7—C8	6.8 (3)	C13—C14—C15—C10	54.4 (2)
C1—C7—C8—C9	177.37 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	1.00 (2)	1.80 (2)	2.7878 (19)	172.0 (15)
N1—H1B···O2^i	0.93 (2)	1.86 (2)	2.7907 (19)	175.1 (17)
N1—H1C···O1^ii	0.96 (2)	1.76 (2)	2.7123 (18)	170.1 (18)

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

(IIIa) cycloheptylaminium cinnamate

Crystal data

C7H16N^+·C9H7O2^−	F(000) = 568
Mr = 261.35	Dx = 1.164 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1437 reflections
a = 5.7790 (4) Å	θ = 2.5–26.3°
b = 11.3400 (11) Å	µ = 0.08 mm^−1
c = 22.7510 (15) Å	T = 173 K
V = 1491.0 (2) Å^3	Block, colourless
Z = 4	0.59 × 0.14 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	1513 reflections with I > 2σ(I)
ω scans	Rint = 0.048
Absorption correction: integration (XPREP; Bruker, 2004)	θmax = 28.0°, θmin = 1.8°
Tmin = 0.957, Tmax = 0.996	h = −7→7
5537 measured reflections	k = −14→14
2094 independent reflections	l = −30→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0394P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.084	(Δ/σ)max < 0.001
S = 0.95	Δρmax = 0.14 e Å^−3
2094 reflections	Δρmin = −0.19 e Å^−3
181 parameters

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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
C1	0.2427 (3)	0.37339 (18)	0.70281 (8)	0.0256 (5)
C2	0.4604 (4)	0.4161 (2)	0.71759 (9)	0.0316 (5)
H2	0.5235	0.481	0.6966	0.038*
C3	0.5861 (4)	0.3649 (2)	0.76269 (9)	0.0387 (6)
H3	0.7333	0.3959	0.773	0.046*
C4	0.4980 (4)	0.2685 (2)	0.79279 (9)	0.0406 (6)
H4	0.5843	0.2337	0.8238	0.049*
C5	0.2854 (4)	0.2236 (2)	0.77760 (9)	0.0383 (6)
H5	0.2259	0.1566	0.7976	0.046*
C6	0.1580 (4)	0.27565 (19)	0.73320 (8)	0.0305 (5)
H6	0.0106	0.2444	0.7232	0.037*
C7	0.0931 (4)	0.43320 (18)	0.65971 (8)	0.0263 (5)
H7	−0.0653	0.4107	0.6596	0.032*
C8	0.1546 (4)	0.51463 (18)	0.62119 (8)	0.0276 (5)
H8	0.3134	0.5353	0.618	0.033*
C9	−0.0171 (4)	0.57511 (18)	0.58264 (8)	0.0249 (4)
O1	0.0645 (2)	0.63720 (13)	0.54083 (6)	0.0329 (4)
O2	−0.2280 (3)	0.56363 (14)	0.59246 (6)	0.0356 (4)
C10	0.5521 (4)	0.54344 (18)	0.44979 (8)	0.0295 (5)
H10	0.7188	0.5502	0.4385	0.035*
C11	0.5126 (5)	0.4189 (2)	0.47286 (10)	0.0440 (7)
H11A	0.6097	0.3642	0.4496	0.053*
H11B	0.5681	0.4156	0.514	0.053*
C12	0.2670 (5)	0.3741 (2)	0.47151 (9)	0.0488 (7)
H12A	0.1609	0.4408	0.4793	0.059*
H12B	0.2466	0.3159	0.5035	0.059*
C13	0.1979 (5)	0.3161 (2)	0.41293 (10)	0.0468 (7)
H13A	0.3153	0.2558	0.4029	0.056*
H13B	0.0485	0.2749	0.4185	0.056*
C14	0.1741 (4)	0.4004 (2)	0.36106 (9)	0.0392 (6)
H14A	0.1481	0.3531	0.3251	0.047*
H14B	0.0345	0.4494	0.3673	0.047*
C15	0.3789 (4)	0.4821 (2)	0.35036 (9)	0.0369 (6)
H15A	0.3601	0.5197	0.3114	0.044*
H15B	0.5221	0.4342	0.3491	0.044*
C16	0.4079 (4)	0.5784 (2)	0.39664 (8)	0.0338 (5)
H16A	0.4808	0.6478	0.3778	0.041*
H16B	0.2526	0.6027	0.4104	0.041*
N1	0.5074 (3)	0.62991 (18)	0.49809 (7)	0.0261 (4)
H1A	0.347 (4)	0.620 (2)	0.5127 (9)	0.039*
H1B	0.530 (4)	0.704 (2)	0.4858 (9)	0.039*
H1C	0.621 (4)	0.616 (2)	0.5311 (9)	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0313 (11)	0.0267 (11)	0.0190 (9)	0.0027 (11)	0.0005 (8)	−0.0013 (9)
C2	0.0347 (11)	0.0326 (12)	0.0274 (10)	0.0004 (10)	0.0019 (10)	0.0038 (10)
C3	0.0351 (12)	0.0453 (14)	0.0356 (12)	0.0058 (12)	−0.0053 (10)	−0.0028 (12)
C4	0.0490 (15)	0.0468 (15)	0.0262 (11)	0.0192 (13)	−0.0027 (11)	0.0057 (11)
C5	0.0504 (14)	0.0313 (12)	0.0331 (11)	0.0108 (12)	0.0097 (12)	0.0082 (11)
C6	0.0374 (12)	0.0271 (11)	0.0269 (11)	0.0003 (10)	0.0046 (10)	−0.0014 (10)
C7	0.0290 (11)	0.0291 (11)	0.0207 (9)	−0.0007 (10)	−0.0007 (8)	−0.0034 (9)
C8	0.0281 (11)	0.0312 (12)	0.0234 (10)	−0.0009 (10)	−0.0016 (9)	0.0003 (10)
C9	0.0296 (11)	0.0260 (11)	0.0191 (9)	0.0007 (9)	0.0007 (9)	−0.0032 (9)
O1	0.0364 (8)	0.0315 (8)	0.0309 (8)	0.0049 (8)	0.0071 (7)	0.0093 (7)
O2	0.0294 (8)	0.0520 (10)	0.0253 (7)	−0.0009 (8)	−0.0032 (6)	0.0070 (8)
C10	0.0312 (11)	0.0308 (12)	0.0264 (10)	0.0058 (10)	−0.0006 (9)	−0.0007 (10)
C11	0.0702 (18)	0.0272 (12)	0.0345 (12)	0.0097 (14)	−0.0130 (12)	0.0028 (10)
C12	0.0838 (19)	0.0307 (13)	0.0318 (12)	−0.0112 (16)	0.0032 (13)	0.0051 (11)
C13	0.0709 (18)	0.0330 (13)	0.0364 (12)	−0.0083 (13)	0.0062 (13)	−0.0049 (11)
C14	0.0464 (14)	0.0398 (14)	0.0315 (12)	−0.0012 (12)	−0.0029 (10)	−0.0075 (11)
C15	0.0489 (14)	0.0398 (13)	0.0220 (10)	−0.0024 (12)	−0.0003 (10)	−0.0005 (10)
C16	0.0444 (14)	0.0319 (12)	0.0252 (10)	−0.0022 (11)	−0.0029 (9)	0.0058 (10)
N1	0.0304 (10)	0.0253 (9)	0.0227 (8)	−0.0009 (9)	−0.0024 (8)	0.0036 (8)

Geometric parameters (Å, º)

C1—C2	1.390 (3)	C10—H10	1
C1—C6	1.395 (3)	C11—C12	1.507 (4)
C1—C7	1.473 (3)	C11—H11A	0.99
C2—C3	1.385 (3)	C11—H11B	0.99
C2—H2	0.95	C12—C13	1.539 (3)
C3—C4	1.387 (3)	C12—H12A	0.99
C3—H3	0.95	C12—H12B	0.99
C4—C5	1.374 (3)	C13—C14	1.525 (3)
C4—H4	0.95	C13—H13A	0.99
C5—C6	1.383 (3)	C13—H13B	0.99
C5—H5	0.95	C14—C15	1.523 (3)
C6—H6	0.95	C14—H14A	0.99
C7—C8	1.322 (3)	C14—H14B	0.99
C7—H7	0.95	C15—C16	1.526 (3)
C8—C9	1.491 (3)	C15—H15A	0.99
C8—H8	0.95	C15—H15B	0.99
C9—O2	1.246 (2)	C16—H16A	0.99
C9—O1	1.274 (2)	C16—H16B	0.99
C10—N1	1.495 (3)	N1—H1A	0.99 (2)
C10—C16	1.521 (3)	N1—H1B	0.89 (3)
C10—C11	1.524 (3)	N1—H1C	1.01 (2)
C2—C1—C6	118.35 (19)	H11A—C11—H11B	107.3
C2—C1—C7	122.14 (19)	C11—C12—C13	114.0 (2)
C6—C1—C7	119.33 (19)	C11—C12—H12A	108.8
C3—C2—C1	120.5 (2)	C13—C12—H12A	108.8
C3—C2—H2	119.7	C11—C12—H12B	108.8
C1—C2—H2	119.7	C13—C12—H12B	108.8
C2—C3—C4	120.3 (2)	H12A—C12—H12B	107.7
C2—C3—H3	119.9	C14—C13—C12	115.21 (19)
C4—C3—H3	119.9	C14—C13—H13A	108.5
C5—C4—C3	119.8 (2)	C12—C13—H13A	108.5
C5—C4—H4	120.1	C14—C13—H13B	108.5
C3—C4—H4	120.1	C12—C13—H13B	108.5
C4—C5—C6	120.1 (2)	H13A—C13—H13B	107.5
C4—C5—H5	120	C15—C14—C13	115.8 (2)
C6—C5—H5	120	C15—C14—H14A	108.3
C5—C6—C1	121.0 (2)	C13—C14—H14A	108.3
C5—C6—H6	119.5	C15—C14—H14B	108.3
C1—C6—H6	119.5	C13—C14—H14B	108.3
C8—C7—C1	127.3 (2)	H14A—C14—H14B	107.4
C8—C7—H7	116.4	C14—C15—C16	114.22 (19)
C1—C7—H7	116.4	C14—C15—H15A	108.7
C7—C8—C9	122.17 (19)	C16—C15—H15A	108.7
C7—C8—H8	118.9	C14—C15—H15B	108.7
C9—C8—H8	118.9	C16—C15—H15B	108.7
O2—C9—O1	123.61 (19)	H15A—C15—H15B	107.6
O2—C9—C8	119.82 (18)	C10—C16—C15	114.97 (18)
O1—C9—C8	116.57 (18)	C10—C16—H16A	108.5
N1—C10—C16	108.61 (16)	C15—C16—H16A	108.5
N1—C10—C11	109.19 (17)	C10—C16—H16B	108.5
C16—C10—C11	115.68 (19)	C15—C16—H16B	108.5
N1—C10—H10	107.7	H16A—C16—H16B	107.5
C16—C10—H10	107.7	C10—N1—H1A	109.7 (13)
C11—C10—H10	107.7	C10—N1—H1B	111.0 (14)
C12—C11—C10	116.5 (2)	H1A—N1—H1B	110 (2)
C12—C11—H11A	108.2	C10—N1—H1C	109.6 (12)
C10—C11—H11A	108.2	H1A—N1—H1C	110.0 (16)
C12—C11—H11B	108.2	H1B—N1—H1C	107 (2)
C10—C11—H11B	108.2
C6—C1—C2—C3	−2.0 (3)	C7—C8—C9—O2	11.5 (3)
C7—C1—C2—C3	173.2 (2)	C7—C8—C9—O1	−168.77 (19)
C1—C2—C3—C4	1.4 (3)	N1—C10—C11—C12	85.0 (2)
C2—C3—C4—C5	0.2 (3)	C16—C10—C11—C12	−37.8 (3)
C3—C4—C5—C6	−1.2 (3)	C10—C11—C12—C13	86.9 (3)
C4—C5—C6—C1	0.6 (3)	C11—C12—C13—C14	−70.0 (3)
C2—C1—C6—C5	1.1 (3)	C12—C13—C14—C15	51.4 (3)
C7—C1—C6—C5	−174.27 (18)	C13—C14—C15—C16	−70.5 (3)
C2—C1—C7—C8	15.7 (3)	N1—C10—C16—C15	−163.24 (18)
C6—C1—C7—C8	−169.1 (2)	C11—C10—C16—C15	−40.1 (3)
C1—C7—C8—C9	−175.43 (18)	C14—C15—C16—C10	87.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.99 (2)	1.76 (2)	2.739 (2)	167 (2)
N1—H1B···O1^i	0.89 (3)	1.92 (3)	2.805 (2)	178 (2)
N1—H1C···O2^ii	1.01 (2)	1.75 (2)	2.741 (2)	166 (2)

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

(IIIb) cycloheptylaminium cinnamate

Crystal data

C7H16N^+·C9H7O2^−	F(000) = 1136
Mr = 261.35	Dx = 1.156 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5663 reflections
a = 11.4496 (2) Å	θ = 2.4–23.1°
b = 6.1011 (1) Å	µ = 0.08 mm^−1
c = 43.0883 (8) Å	T = 173 K
β = 93.659 (1)°	Needle, colourless
V = 3003.80 (9) Å^3	0.45 × 0.3 × 0.21 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer	4684 reflections with I > 2σ(I)
ω scans	Rint = 0.047
Absorption correction: multi-scan (XPREP; Bruker, 2004)	θmax = 28°, θmin = 1.8°
Tmin = 0.967, Tmax = 0.984	h = −14→15
37019 measured reflections	k = −7→7
7152 independent reflections	l = −54→56

Refinement

Refinement on F^2	31 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.0718P)^2 + 0.3266P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.149	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.25 e Å^−3
7152 reflections	Δρmin = −0.29 e Å^−3
487 parameters

Special details

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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	Occ. (<1)
C1A	0.3468 (4)	0.5922 (7)	0.15153 (10)	0.0328 (13)	0.583 (5)
C2A	0.4384 (4)	0.4561 (5)	0.14418 (9)	0.0463 (11)	0.583 (5)
H2D	0.4497	0.3194	0.1545	0.056*	0.583 (5)
C3A	0.5136 (3)	0.5202 (6)	0.12177 (8)	0.0501 (11)	0.583 (5)
H3A	0.5762	0.4272	0.1168	0.06*	0.583 (5)
C4A	0.4971 (3)	0.7203 (7)	0.10670 (6)	0.0452 (13)	0.583 (5)
H4A	0.5485	0.7641	0.0914	0.054*	0.583 (5)
C5A	0.4055 (4)	0.8563 (4)	0.11404 (9)	0.0502 (12)	0.583 (5)
H5A	0.3943	0.9931	0.1037	0.06*	0.583 (5)
C6A	0.3303 (3)	0.7923 (6)	0.13646 (11)	0.0412 (14)	0.583 (5)
H6A	0.2677	0.8853	0.1415	0.049*	0.583 (5)
C7A	0.2612 (2)	0.5224 (5)	0.17422 (6)	0.0337 (8)	0.583 (5)
H7A	0.2142	0.6333	0.1826	0.04*	0.583 (5)
C8A	0.2451 (2)	0.3203 (6)	0.18364 (6)	0.0360 (8)	0.583 (5)
H8A	0.2931	0.2103	0.1754	0.043*	0.583 (5)
C9A	0.1588 (6)	0.2468 (12)	0.20600 (17)	0.0254 (13)	0.583 (5)
O1A	0.1477 (7)	0.0431 (10)	0.2084 (2)	0.0467 (11)	0.583 (5)
O2A	0.0963 (6)	0.3882 (10)	0.21879 (12)	0.0435 (10)	0.583 (5)
C1B	0.3484 (7)	0.5380 (13)	0.14678 (18)	0.0385 (17)	0.417 (5)
C2B	0.4453 (6)	0.4759 (10)	0.13152 (17)	0.0510 (15)	0.417 (5)
H2E	0.4767	0.3335	0.1352	0.061*	0.417 (5)
C3B	0.4983 (6)	0.6120 (16)	0.11118 (19)	0.060 (2)	0.417 (5)
H3B	0.5647	0.5636	0.1009	0.072*	0.417 (5)
C4B	0.4531 (7)	0.8228 (16)	0.10580 (15)	0.0560 (18)	0.417 (5)
H4B	0.4878	0.9192	0.0917	0.067*	0.417 (5)
C5B	0.3577 (6)	0.8877 (15)	0.12123 (18)	0.0605 (17)	0.417 (5)
H5B	0.3255	1.0298	0.1178	0.073*	0.417 (5)
C6B	0.3088 (8)	0.7471 (14)	0.1417 (3)	0.055 (2)	0.417 (5)
H6B	0.2447	0.7973	0.1527	0.066*	0.417 (5)
C7B	0.2930 (3)	0.3899 (7)	0.16791 (9)	0.0382 (12)	0.417 (5)
H7B	0.3155	0.2403	0.167	0.046*	0.417 (5)
C8B	0.2152 (4)	0.4388 (8)	0.18821 (9)	0.0380 (11)	0.417 (5)
H8B	0.1963	0.589	0.1908	0.046*	0.417 (5)
C9B	0.1563 (12)	0.2787 (19)	0.2069 (3)	0.054 (4)	0.417 (5)
O1B	0.0981 (9)	0.3507 (14)	0.22889 (16)	0.0462 (15)	0.417 (5)
O2B	0.1728 (11)	0.0765 (16)	0.2032 (3)	0.0556 (19)	0.417 (5)
C10	0.20726 (13)	0.7872 (3)	0.27856 (4)	0.0496 (4)
H10	0.2014	0.9355	0.2882	0.059*
C11	0.18113 (14)	0.6194 (3)	0.30320 (4)	0.0550 (4)
H11A	0.1593	0.4799	0.2926	0.066*	0.835 (3)
H11B	0.1121	0.6703	0.3139	0.066*	0.835 (3)
H11C	0.0976	0.5918	0.3023	0.066*	0.165 (3)
H11D	0.2038	0.6787	0.3236	0.066*	0.165 (3)
C12A	0.27988 (17)	0.5721 (4)	0.32787 (4)	0.0538 (6)	0.835 (3)
H12A	0.3233	0.7095	0.3327	0.065*	0.835 (3)
H12B	0.2455	0.5225	0.3472	0.065*	0.835 (3)
C12B	0.2436 (13)	0.393 (3)	0.2972 (5)	0.213 (18)	0.165 (3)
H12C	0.2573	0.3759	0.2749	0.255*	0.165 (3)
H12D	0.1946	0.2693	0.3037	0.255*	0.165 (3)
C13	0.36543 (18)	0.3983 (4)	0.31773 (5)	0.0729 (6)
H13A	0.4161	0.3546	0.3362	0.087*	0.835 (3)
H13B	0.3198	0.2675	0.3107	0.087*	0.835 (3)
H13C	0.3691	0.504	0.3346	0.087*	0.165 (3)
H13D	0.3841	0.2535	0.3259	0.087*	0.165 (3)
C14	0.44275 (17)	0.4621 (4)	0.29236 (5)	0.0722 (6)
H14A	0.4901	0.3332	0.2871	0.087*	0.835 (3)
H14B	0.4975	0.5774	0.3004	0.087*	0.835 (3)
H14C	0.423	0.3702	0.2744	0.087*	0.165 (3)
H14D	0.5233	0.4313	0.2993	0.087*	0.165 (3)
C15A	0.3781 (2)	0.5464 (4)	0.26252 (5)	0.0657 (8)	0.835 (3)
H15A	0.4332	0.5474	0.2457	0.079*	0.835 (3)
H15B	0.3142	0.4429	0.2564	0.079*	0.835 (3)
C15B	0.4320 (9)	0.711 (3)	0.2831 (3)	0.076 (5)	0.165 (3)
H15C	0.4372	0.7998	0.3024	0.091*	0.165 (3)
H15D	0.4999	0.7507	0.2711	0.091*	0.165 (3)
C16	0.32704 (15)	0.7719 (4)	0.26521 (5)	0.0695 (6)
H16A	0.3213	0.8389	0.2442	0.083*	0.835 (3)
H16B	0.3826	0.8616	0.2784	0.083*	0.835 (3)
H16C	0.3169	0.6757	0.2473	0.083*	0.165 (3)
H16D	0.344	0.9161	0.2571	0.083*	0.165 (3)
N1	0.11365 (12)	0.7726 (3)	0.25288 (3)	0.0469 (3)
H1A	0.1114 (17)	0.629 (4)	0.2428 (4)	0.07*
H1B	0.1237 (17)	0.878 (4)	0.2367 (5)	0.07*
H1C	0.0414 (19)	0.794 (3)	0.2603 (4)	0.07*
C17	0.14996 (11)	0.1313 (2)	0.40206 (3)	0.0340 (3)
C18	0.12382 (13)	0.0346 (3)	0.37316 (3)	0.0450 (4)
H18	0.1564	−0.1041	0.3686	0.054*
C19	0.05049 (15)	0.1394 (3)	0.35100 (4)	0.0527 (4)
H19	0.0328	0.0714	0.3314	0.063*
C20	0.00306 (14)	0.3412 (3)	0.35712 (4)	0.0507 (4)
H20	−0.0469	0.4125	0.3418	0.061*
C21	0.02855 (13)	0.4389 (3)	0.38553 (4)	0.0484 (4)
H21	−0.0038	0.5781	0.3899	0.058*
C22	0.10139 (12)	0.3345 (2)	0.40781 (4)	0.0405 (3)
H22	0.1184	0.4032	0.4274	0.049*
C23	0.22490 (11)	0.0255 (2)	0.42674 (3)	0.0342 (3)
H23	0.2433	0.1107	0.4448	0.041*
C24	0.26950 (11)	−0.1737 (2)	0.42665 (3)	0.0341 (3)
H24	0.2525	−0.262	0.4088	0.041*
C25	0.34476 (11)	−0.2698 (2)	0.45266 (3)	0.0313 (3)
O3	0.38006 (9)	−0.46245 (16)	0.44897 (2)	0.0416 (3)
O4	0.37025 (8)	−0.15742 (16)	0.47688 (2)	0.0381 (2)
C26	0.32752 (12)	0.3396 (2)	0.52485 (3)	0.0383 (3)
H26	0.3626	0.4774	0.5339	0.046*
C27	0.20571 (13)	0.3952 (3)	0.51090 (4)	0.0487 (4)
H27A	0.178	0.2759	0.4967	0.058*	0.616 (3)
H27B	0.2095	0.5315	0.4986	0.058*	0.616 (3)
H27C	0.2139	0.4677	0.4911	0.058*	0.384 (3)
H27D	0.1716	0.5005	0.5246	0.058*	0.384 (3)
C28A	0.1182 (2)	0.4259 (5)	0.53605 (7)	0.0556 (8)	0.616 (3)
H28A	0.0605	0.5408	0.5297	0.067*	0.616 (3)
H28B	0.1596	0.4706	0.5559	0.067*	0.616 (3)
C28B	0.1169 (4)	0.1972 (9)	0.50578 (10)	0.0550 (13)	0.384 (3)
H28C	0.1583	0.0583	0.502	0.066*	0.384 (3)
H28D	0.059	0.2258	0.4882	0.066*	0.384 (3)
C29	0.05271 (18)	0.1917 (4)	0.54013 (6)	0.0921 (8)
H29A	−0.0246	0.2155	0.5487	0.11*	0.616 (3)
H29B	0.0402	0.1187	0.5197	0.11*	0.616 (3)
H29C	0.0487	0.3381	0.5488	0.11*	0.384 (3)
H29D	−0.0261	0.1336	0.5374	0.11*	0.384 (3)
C30	0.12780 (19)	0.0494 (4)	0.56195 (5)	0.0735 (6)
H30A	0.0831	−0.0833	0.5671	0.088*	0.616 (3)
H30B	0.1468	0.1305	0.5815	0.088*	0.616 (3)
H30C	0.0855	0.0035	0.5796	0.088*	0.384 (3)
H30D	0.1537	−0.0795	0.5511	0.088*	0.384 (3)
C31A	0.2451 (3)	−0.0219 (5)	0.54751 (7)	0.0574 (8)	0.616 (3)
H31A	0.2778	−0.1526	0.5586	0.069*	0.616 (3)
H31B	0.2292	−0.0606	0.5253	0.069*	0.616 (3)
C31B	0.2306 (4)	0.1986 (9)	0.57275 (10)	0.0573 (13)	0.384 (3)
H31C	0.258	0.1611	0.5943	0.069*	0.384 (3)
H31D	0.2048	0.3535	0.5723	0.069*	0.384 (3)
C32	0.33391 (15)	0.1671 (3)	0.55040 (4)	0.0526 (4)
H32A	0.3243	0.2422	0.5704	0.063*	0.616 (3)
H32B	0.4135	0.1028	0.5514	0.063*	0.616 (3)
H32C	0.4081	0.1793	0.5625	0.063*	0.384 (3)
H32D	0.3298	0.0222	0.5411	0.063*	0.384 (3)
N2	0.40192 (10)	0.2666 (2)	0.49937 (3)	0.0322 (3)
H2A	0.3774 (14)	0.128 (3)	0.4911 (4)	0.048*
H2B	0.4820 (16)	0.245 (3)	0.5069 (4)	0.048*
H2C	0.3960 (14)	0.372 (3)	0.4819 (4)	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0342 (19)	0.031 (3)	0.033 (2)	−0.0002 (16)	0.0041 (14)	−0.0013 (18)
C2A	0.044 (2)	0.048 (2)	0.049 (3)	0.0027 (14)	0.015 (2)	0.0161 (17)
C3A	0.054 (2)	0.046 (3)	0.052 (2)	0.0110 (17)	0.0189 (18)	0.0100 (16)
C4A	0.047 (3)	0.051 (4)	0.0384 (18)	0.003 (2)	0.0129 (16)	0.012 (2)
C5A	0.042 (4)	0.048 (2)	0.062 (4)	0.001 (2)	0.018 (2)	0.019 (2)
C6A	0.043 (2)	0.031 (2)	0.052 (3)	0.0009 (18)	0.011 (2)	0.0091 (19)
C7A	0.0330 (13)	0.0331 (18)	0.0353 (14)	0.0033 (12)	0.0042 (11)	−0.0041 (12)
C8A	0.0356 (14)	0.037 (2)	0.0368 (15)	0.0030 (13)	0.0100 (12)	−0.0011 (13)
C9A	0.021 (2)	0.032 (3)	0.023 (2)	0.0015 (17)	0.0059 (18)	0.0031 (17)
O1A	0.061 (3)	0.036 (2)	0.044 (2)	−0.0004 (17)	0.0095 (15)	0.0065 (16)
O2A	0.0396 (14)	0.043 (2)	0.050 (3)	−0.0060 (14)	0.017 (2)	−0.0098 (18)
C1B	0.041 (3)	0.039 (3)	0.036 (3)	−0.008 (2)	0.004 (2)	−0.004 (3)
C2B	0.047 (3)	0.046 (3)	0.062 (4)	0.001 (2)	0.017 (4)	−0.007 (3)
C3B	0.048 (3)	0.078 (7)	0.056 (4)	0.006 (3)	0.023 (3)	−0.019 (4)
C4B	0.045 (5)	0.079 (5)	0.045 (3)	−0.012 (4)	0.013 (3)	0.003 (3)
C5B	0.049 (4)	0.076 (4)	0.059 (4)	−0.003 (3)	0.024 (3)	0.008 (3)
C6B	0.055 (3)	0.057 (4)	0.056 (3)	−0.011 (3)	0.024 (3)	0.009 (3)
C7B	0.044 (2)	0.030 (2)	0.041 (2)	0.0050 (18)	0.0013 (18)	−0.0030 (18)
C8B	0.048 (2)	0.029 (2)	0.038 (2)	0.002 (2)	0.0057 (18)	0.0013 (19)
C9B	0.064 (7)	0.038 (5)	0.056 (6)	−0.005 (4)	−0.019 (5)	0.003 (4)
O1B	0.046 (2)	0.039 (3)	0.054 (4)	−0.0057 (19)	0.013 (3)	−0.009 (3)
O2B	0.085 (6)	0.030 (3)	0.052 (4)	0.000 (3)	0.005 (3)	0.002 (3)
C10	0.0400 (8)	0.0498 (10)	0.0586 (10)	−0.0052 (7)	0.0010 (7)	−0.0102 (8)
C11	0.0416 (9)	0.0675 (12)	0.0565 (10)	−0.0037 (8)	0.0067 (7)	−0.0031 (9)
C12A	0.0410 (11)	0.0755 (16)	0.0451 (11)	0.0015 (10)	0.0038 (8)	−0.0053 (10)
C12B	0.37 (5)	0.17 (3)	0.102 (15)	−0.14 (3)	0.07 (2)	−0.032 (16)
C13	0.0617 (12)	0.0854 (16)	0.0709 (13)	0.0154 (11)	−0.0015 (10)	0.0051 (11)
C14	0.0491 (10)	0.1009 (18)	0.0661 (12)	0.0213 (11)	0.0011 (9)	−0.0074 (12)
C15A	0.0493 (13)	0.091 (2)	0.0578 (13)	0.0110 (12)	0.0135 (10)	−0.0049 (12)
C15B	0.037 (6)	0.129 (13)	0.059 (7)	−0.022 (6)	−0.012 (5)	0.039 (7)
C16	0.0407 (9)	0.0880 (16)	0.0807 (13)	−0.0051 (9)	0.0113 (9)	0.0125 (11)
N1	0.0414 (7)	0.0406 (8)	0.0586 (9)	0.0029 (6)	0.0027 (6)	−0.0107 (7)
C17	0.0274 (6)	0.0378 (8)	0.0369 (7)	−0.0029 (6)	0.0023 (5)	0.0039 (6)
C18	0.0461 (8)	0.0461 (10)	0.0422 (8)	0.0032 (7)	−0.0011 (7)	0.0007 (7)
C19	0.0531 (10)	0.0633 (12)	0.0401 (8)	−0.0046 (9)	−0.0100 (7)	0.0028 (8)
C20	0.0385 (8)	0.0584 (11)	0.0540 (10)	−0.0018 (8)	−0.0074 (7)	0.0191 (8)
C21	0.0418 (8)	0.0418 (10)	0.0616 (10)	0.0033 (7)	0.0030 (7)	0.0102 (8)
C22	0.0366 (7)	0.0395 (9)	0.0451 (8)	−0.0017 (6)	0.0009 (6)	0.0020 (7)
C23	0.0316 (7)	0.0375 (8)	0.0335 (7)	−0.0021 (6)	0.0034 (5)	−0.0022 (6)
C24	0.0347 (7)	0.0354 (8)	0.0322 (7)	−0.0054 (6)	0.0024 (5)	−0.0010 (6)
C25	0.0306 (7)	0.0312 (8)	0.0324 (7)	−0.0039 (6)	0.0052 (5)	0.0020 (6)
O3	0.0561 (6)	0.0308 (6)	0.0380 (5)	0.0046 (5)	0.0034 (5)	−0.0010 (4)
O4	0.0420 (5)	0.0330 (6)	0.0383 (5)	0.0021 (4)	−0.0047 (4)	−0.0044 (4)
C26	0.0403 (8)	0.0350 (8)	0.0403 (8)	−0.0067 (6)	0.0085 (6)	−0.0063 (6)
C27	0.0423 (9)	0.0481 (10)	0.0573 (10)	0.0026 (7)	0.0148 (7)	0.0029 (8)
C28A	0.0457 (15)	0.0492 (18)	0.0746 (19)	0.0003 (12)	0.0261 (14)	−0.0080 (14)
C28B	0.039 (2)	0.073 (3)	0.053 (3)	−0.014 (2)	0.0062 (19)	−0.010 (2)
C29	0.0519 (12)	0.0981 (19)	0.131 (2)	−0.0138 (12)	0.0432 (13)	0.0144 (16)
C30	0.0774 (14)	0.0665 (14)	0.0810 (13)	−0.0257 (11)	0.0399 (11)	−0.0011 (11)
C31A	0.0666 (18)	0.0430 (17)	0.0654 (18)	−0.0036 (13)	0.0251 (15)	0.0015 (13)
C31B	0.051 (3)	0.076 (3)	0.045 (2)	−0.016 (2)	0.0097 (19)	0.005 (2)
C32	0.0556 (10)	0.0615 (12)	0.0415 (8)	−0.0087 (8)	0.0082 (7)	0.0071 (8)
N2	0.0324 (6)	0.0276 (7)	0.0366 (6)	0.0001 (5)	0.0022 (5)	−0.0006 (5)

Geometric parameters (Å, º)

C1A—C2A	1.39	C15B—H15C	0.99
C1A—C6A	1.39	C15B—H15D	0.99
C1A—C7A	1.490 (4)	C16—H16A	0.99
C2A—C3A	1.39	C16—H16B	0.99
C2A—H2D	0.95	C16—H16C	0.97
C3A—C4A	1.39	C16—H16D	0.97
C3A—H3A	0.95	N1—H1A	0.98 (2)
C4A—C5A	1.39	N1—H1B	0.96 (2)
C4A—H4A	0.95	N1—H1C	0.91 (2)
C5A—C6A	1.39	C17—C22	1.388 (2)
C5A—H5A	0.95	C17—C18	1.393 (2)
C6A—H6A	0.95	C17—C23	1.4720 (19)
C7A—C8A	1.315 (5)	C18—C19	1.387 (2)
C7A—H7A	0.95	C18—H18	0.95
C8A—C9A	1.493 (4)	C19—C20	1.378 (2)
C8A—H8A	0.95	C19—H19	0.95
C9A—O1A	1.254 (6)	C20—C21	1.376 (2)
C9A—O2A	1.268 (7)	C20—H20	0.95
C1B—C6B	1.367 (8)	C21—C22	1.386 (2)
C1B—C2B	1.378 (7)	C21—H21	0.95
C1B—C7B	1.456 (7)	C22—H22	0.95
C2B—C3B	1.376 (8)	C23—C24	1.3181 (19)
C2B—H2E	0.95	C23—H23	0.95
C3B—C4B	1.400 (9)	C24—C25	1.4900 (19)
C3B—H3B	0.95	C24—H24	0.95
C4B—C5B	1.373 (7)	C25—O3	1.2563 (16)
C4B—H4B	0.95	C25—O4	1.2670 (16)
C5B—C6B	1.374 (8)	C26—N2	1.4994 (17)
C5B—H5B	0.95	C26—C27	1.521 (2)
C6B—H6B	0.95	C26—C32	1.521 (2)
C7B—C8B	1.322 (7)	C26—H26	1
C7B—H7B	0.95	C27—C28A	1.533 (3)
C8B—C9B	1.458 (10)	C27—C28B	1.585 (5)
C8B—H8B	0.95	C27—H27A	0.99
C9B—O2B	1.260 (8)	C27—H27B	0.99
C9B—O1B	1.271 (8)	C27—H27C	0.97
C10—N1	1.493 (2)	C27—H27D	0.97
C10—C11	1.518 (2)	C28A—C29	1.629 (4)
C10—C16	1.524 (2)	C28A—H27D	0.9296
C10—H10	1	C28A—H28A	0.99
C11—C12A	1.529 (3)	C28A—H28B	0.99
C11—C12B	1.584 (14)	C28A—H29C	1.1307
C11—H11A	0.99	C28B—C29	1.694 (5)
C11—H11B	0.99	C28B—H28C	0.99
C11—H11C	0.97	C28B—H28D	0.99
C11—H11D	0.9699	C29—C30	1.508 (3)
C12A—C13	1.526 (3)	C29—H29A	0.99
C12A—H11D	1.0936	C29—H29B	0.99
C12A—H12A	0.99	C29—H29C	0.97
C12A—H12B	0.99	C29—H29D	0.97
C12A—H13C	1.1238	C30—C31B	1.536 (5)
C12B—C13	1.603 (14)	C30—C31A	1.577 (3)
C12B—H12C	0.99	C30—H30A	0.99
C12B—H12D	0.99	C30—H30B	0.99
C13—C14	1.501 (3)	C30—H30C	0.9701
C13—H13A	0.99	C30—H30D	0.97
C13—H13B	0.99	C31A—C32	1.537 (3)
C13—H13C	0.97	C31A—H30D	1.1245
C13—H13D	0.97	C31A—H31A	0.99
C14—C15A	1.531 (3)	C31A—H31B	0.99
C14—C15B	1.574 (14)	C31A—H32D	1.0587
C14—H14A	0.99	C31B—C32	1.584 (4)
C14—H14B	0.99	C31B—H31C	0.99
C14—H14C	0.97	C31B—H31D	0.99
C14—H14D	0.97	C32—H32A	0.99
C15A—C16	1.502 (3)	C32—H32B	0.99
C15A—H14C	1.2844	C32—H32C	0.9699
C15A—H15A	0.99	C32—H32D	0.97
C15A—H15B	0.99	N2—H2A	0.953 (18)
C15A—H16C	1.2183	N2—H2B	0.962 (18)
C15B—C16	1.435 (10)	N2—H2C	0.986 (17)
C2A—C1A—C6A	120	C15A—C16—H16C	54
C2A—C1A—C7A	121.1 (3)	C10—C16—H16C	105.8
C6A—C1A—C7A	118.8 (3)	H16A—C16—H16C	61.8
C3A—C2A—C1A	120	H16B—C16—H16C	146.1
C3A—C2A—H2D	120	C15B—C16—H16D	104.3
C1A—C2A—H2D	120	C15A—C16—H16D	135.6
C2A—C3A—C4A	120	C10—C16—H16D	106.6
C2A—C3A—H3A	120	H16A—C16—H16D	45.7
C4A—C3A—H3A	120	H16B—C16—H16D	64.4
C5A—C4A—C3A	120	H16C—C16—H16D	106.3
C5A—C4A—H4A	120	C10—N1—H1A	112.4 (11)
C3A—C4A—H4A	120	C10—N1—H1B	112.6 (12)
C4A—C5A—C6A	120	H1A—N1—H1B	106.1 (16)
C4A—C5A—H5A	120	C10—N1—H1C	110.8 (12)
C6A—C5A—H5A	120	H1A—N1—H1C	106.5 (17)
C5A—C6A—C1A	120	H1B—N1—H1C	108.1 (17)
C5A—C6A—H6A	120	C22—C17—C18	118.19 (13)
C1A—C6A—H6A	120	C22—C17—C23	118.97 (13)
C8A—C7A—C1A	125.5 (3)	C18—C17—C23	122.83 (14)
C8A—C7A—H7A	117.2	C19—C18—C17	120.41 (16)
C1A—C7A—H7A	117.2	C19—C18—H18	119.8
C7A—C8A—C9A	126.3 (4)	C17—C18—H18	119.8
C7A—C8A—H8A	116.8	C20—C19—C18	120.61 (16)
C9A—C8A—H8A	116.8	C20—C19—H19	119.7
O1A—C9A—O2A	125.1 (5)	C18—C19—H19	119.7
O1A—C9A—C8A	115.2 (4)	C21—C20—C19	119.55 (15)
O2A—C9A—C8A	119.4 (5)	C21—C20—H20	120.2
C6B—C1B—C2B	116.7 (5)	C19—C20—H20	120.2
C6B—C1B—C7B	121.7 (7)	C20—C21—C22	120.10 (16)
C2B—C1B—C7B	121.6 (7)	C20—C21—H21	120
C3B—C2B—C1B	122.7 (5)	C22—C21—H21	120
C3B—C2B—H2E	118.7	C21—C22—C17	121.14 (15)
C1B—C2B—H2E	118.7	C21—C22—H22	119.4
C2B—C3B—C4B	119.1 (5)	C17—C22—H22	119.4
C2B—C3B—H3B	120.5	C24—C23—C17	127.59 (13)
C4B—C3B—H3B	120.5	C24—C23—H23	116.2
C5B—C4B—C3B	118.8 (8)	C17—C23—H23	116.2
C5B—C4B—H4B	120.6	C23—C24—C25	124.48 (13)
C3B—C4B—H4B	120.6	C23—C24—H24	117.8
C4B—C5B—C6B	120.0 (10)	C25—C24—H24	117.8
C4B—C5B—H5B	120	O3—C25—O4	123.47 (12)
C6B—C5B—H5B	120	O3—C25—C24	116.63 (12)
C1B—C6B—C5B	122.7 (7)	O4—C25—C24	119.90 (12)
C1B—C6B—H6B	118.6	N2—C26—C27	109.05 (12)
C5B—C6B—H6B	118.6	N2—C26—C32	108.74 (12)
C8B—C7B—C1B	127.8 (5)	C27—C26—C32	116.14 (13)
C8B—C7B—H7B	116.1	N2—C26—H26	107.5
C1B—C7B—H7B	116.1	C27—C26—H26	107.5
C7B—C8B—C9B	124.7 (6)	C32—C26—H26	107.5
C7B—C8B—H8B	117.6	C26—C27—C28A	111.84 (17)
C9B—C8B—H8B	117.6	C26—C27—C28B	116.7 (2)
O2B—C9B—O1B	121.6 (9)	C28A—C27—C28B	75.5 (2)
O2B—C9B—C8B	120.4 (7)	C26—C27—H27A	109.2
O1B—C9B—C8B	117.6 (9)	C28A—C27—H27A	109.2
N1—C10—C11	108.30 (13)	C28B—C27—H27A	34.6
N1—C10—C16	109.71 (14)	C26—C27—H27B	109.2
C11—C10—C16	116.44 (15)	C28A—C27—H27B	109.2
N1—C10—H10	107.3	C28B—C27—H27B	127.9
C11—C10—H10	107.3	H27A—C27—H27B	107.9
C16—C10—H10	107.3	C26—C27—H27C	108.1
C10—C11—C12A	116.32 (15)	C28A—C27—H27C	132
C10—C11—C12B	111.3 (8)	C28B—C27—H27C	108.8
C12A—C11—C12B	68.1 (7)	H27A—C27—H27C	80.6
C10—C11—H11A	108.2	C26—C27—H27D	107.6
C12A—C11—H11A	108.2	C28B—C27—H27D	108.1
C10—C11—H11B	108.2	H27A—C27—H27D	137.5
C12A—C11—H11B	108.2	H27B—C27—H27D	78.6
C12B—C11—H11B	137	H27C—C27—H27D	107.2
H11A—C11—H11B	107.4	C27—C28A—C29	107.2 (2)
C10—C11—H11C	109.1	C29—C28A—H27D	144.1
C12A—C11—H11C	132.7	C27—C28A—H28A	110.3
C12B—C11—H11C	107.2	C29—C28A—H28A	110.3
H11A—C11—H11C	67.2	H27D—C28A—H28A	87.6
C10—C11—H11D	109.2	C27—C28A—H28B	110.3
C12A—C11—H11D	45.4	C29—C28A—H28B	110.3
C12B—C11—H11D	112	H27D—C28A—H28B	91.8
H11A—C11—H11D	141.6	H28A—C28A—H28B	108.5
H11B—C11—H11D	68.7	C27—C28A—H29C	142.9
H11C—C11—H11D	107.8	H27D—C28A—H29C	176.2
C13—C12A—C11	113.05 (17)	H28A—C28A—H29C	89.4
C13—C12A—H11D	152.1	H28B—C28A—H29C	91.4
C13—C12A—H12A	109	C27—C28B—C29	101.7 (3)
C11—C12A—H12A	109	C27—C28B—H28C	111.4
H11D—C12A—H12A	85.2	C29—C28B—H28C	111.4
C13—C12A—H12B	109	C27—C28B—H28D	111.4
C11—C12A—H12B	109	C29—C28B—H28D	111.4
H11D—C12A—H12B	88.2	H28C—C28B—H28D	109.3
H12A—C12A—H12B	107.8	C30—C29—C28A	108.9 (2)
C11—C12A—H13C	150.3	C30—C29—C28B	107.1 (2)
H11D—C12A—H13C	164.8	C28A—C29—C28B	70.1 (2)
H12A—C12A—H13C	79.8	C30—C29—H29A	109.9
H12B—C12A—H13C	94.3	C28A—C29—H29A	109.9
C11—C12B—C13	106.2 (13)	C28B—C29—H29A	140.3
C11—C12B—H12C	110.5	C30—C29—H29B	109.9
C13—C12B—H12C	110.5	C28A—C29—H29B	109.9
C11—C12B—H12D	110.5	H29A—C29—H29B	108.3
C13—C12B—H12D	110.5	C30—C29—H29C	109.3
H12C—C12B—H12D	108.7	C28B—C29—H29C	110.6
C14—C13—C12A	116.57 (19)	H29A—C29—H29C	69.9
C14—C13—C12B	97.9 (8)	H29B—C29—H29C	138.5
C12A—C13—C12B	67.7 (7)	C30—C29—H29D	110.8
C14—C13—H13A	108.1	C28A—C29—H29D	137.7
C12A—C13—H13A	108.1	C28B—C29—H29D	110.6
C12B—C13—H13A	151.8	H29B—C29—H29D	69.2
C14—C13—H13B	108.1	H29C—C29—H29D	108.5
C12A—C13—H13B	108.1	C29—C30—C31B	104.0 (3)
C12B—C13—H13B	52.6	C29—C30—C31A	112.25 (18)
H13A—C13—H13B	107.3	C31B—C30—C31A	68.1 (2)
C14—C13—H13C	111.9	C29—C30—H30A	109.2
C12A—C13—H13C	47.3	C31B—C30—H30A	144.4
C12B—C13—H13C	114.9	C31A—C30—H30A	109.2
H13A—C13—H13C	65.4	C29—C30—H30B	109.2
H13B—C13—H13C	139.5	C31B—C30—H30B	47.4
C14—C13—H13D	111.9	C31A—C30—H30B	109.2
C12A—C13—H13D	131.3	H30A—C30—H30B	107.9
C12B—C13—H13D	110.2	C29—C30—H30C	111.2
H13A—C13—H13D	50.1	C31B—C30—H30C	110.1
H13B—C13—H13D	58.4	C31A—C30—H30C	135.3
H13C—C13—H13D	109.6	H30A—C30—H30C	45.4
C13—C14—C15A	115.01 (16)	H30B—C30—H30C	64.4
C13—C14—C15B	113.2 (5)	C29—C30—H30D	110.3
C15A—C14—C15B	55.8 (4)	C31B—C30—H30D	112
C13—C14—H14A	108.5	C31A—C30—H30D	45
C15A—C14—H14A	108.5	H30A—C30—H30D	67.9
C15B—C14—H14A	138.1	H30B—C30—H30D	139.2
C13—C14—H14B	108.5	H30C—C30—H30D	109.1
C15A—C14—H14B	108.5	C32—C31A—C30	109.7 (2)
C15B—C14—H14B	56	C32—C31A—H30D	147.1
H14A—C14—H14B	107.5	C32—C31A—H31A	109.7
C13—C14—H14C	108.2	C30—C31A—H31A	109.7
C15A—C14—H14C	56.6	H30D—C31A—H31A	90.5
C15B—C14—H14C	110.3	C32—C31A—H31B	109.7
H14A—C14—H14C	57.4	C30—C31A—H31B	109.7
H14B—C14—H14C	143.2	H30D—C31A—H31B	86.8
C13—C14—H14D	108.5	H31A—C31A—H31B	108.2
C15A—C14—H14D	136.4	C30—C31A—H32D	148.1
C15B—C14—H14D	108.8	H30D—C31A—H32D	172.3
H14A—C14—H14D	52.6	H31A—C31A—H32D	90.3
H14B—C14—H14D	57.4	H31B—C31A—H32D	85.7
H14C—C14—H14D	107.6	C30—C31B—C32	109.4 (3)
C16—C15A—C14	114.4 (2)	C30—C31B—H31C	109.8
C16—C15A—H14C	152.1	C32—C31B—H31C	109.8
C16—C15A—H15A	108.7	C30—C31B—H31D	109.8
C14—C15A—H15A	108.7	C32—C31B—H31D	109.8
H14C—C15A—H15A	92.3	H31C—C31B—H31D	108.3
C16—C15A—H15B	108.7	C26—C32—C31A	117.33 (18)
C14—C15A—H15B	108.7	C26—C32—C31B	110.6 (2)
H14C—C15A—H15B	81	C31A—C32—C31B	68.0 (2)
H15A—C15A—H15B	107.6	C26—C32—H32A	108
C14—C15A—H16C	154.1	C31A—C32—H32A	108
H14C—C15A—H16C	163.4	C26—C32—H32B	108
H15A—C15A—H16C	88.5	C31A—C32—H32B	108
H15B—C15A—H16C	83	C31B—C32—H32B	137.8
C16—C15B—C14	115.7 (8)	H32A—C32—H32B	107.2
C16—C15B—H15C	108.4	C26—C32—H32C	109.5
C14—C15B—H15C	108.4	C31A—C32—H32C	130.8
C16—C15B—H15D	108.4	C31B—C32—H32C	109.1
C14—C15B—H15D	108.4	H32A—C32—H32C	68.8
H15C—C15B—H15D	107.4	C26—C32—H32D	109.5
C15B—C16—C15A	59.3 (7)	C31B—C32—H32D	110
C15B—C16—C10	123.7 (5)	H32A—C32—H32D	140.9
C15A—C16—C10	116.70 (17)	H32B—C32—H32D	71.2
C15B—C16—H16A	127	H32C—C32—H32D	108
C15A—C16—H16A	108.1	C26—N2—H2A	111.6 (10)
C10—C16—H16A	108.1	C26—N2—H2B	111.6 (9)
C15B—C16—H16B	49.3	H2A—N2—H2B	104.7 (14)
C15A—C16—H16B	108.1	C26—N2—H2C	110.5 (9)
C10—C16—H16B	108.1	H2A—N2—H2C	106.8 (14)
H16A—C16—H16B	107.3	H2B—N2—H2C	111.3 (14)
C15B—C16—H16C	109
C6A—C1A—C2A—C3A	0	C14—C15A—C16—C15B	31.0 (5)
C7A—C1A—C2A—C3A	176.7 (4)	C14—C15A—C16—C10	−84.1 (2)
C1A—C2A—C3A—C4A	0	N1—C10—C16—C15B	−159.5 (8)
C2A—C3A—C4A—C5A	0	C11—C10—C16—C15B	−36.1 (8)
C3A—C4A—C5A—C6A	0	N1—C10—C16—C15A	−90.1 (2)
C4A—C5A—C6A—C1A	0	C11—C10—C16—C15A	33.3 (3)
C2A—C1A—C6A—C5A	0	C22—C17—C18—C19	−0.4 (2)
C7A—C1A—C6A—C5A	−176.8 (4)	C23—C17—C18—C19	178.50 (14)
C2A—C1A—C7A—C8A	−16.6 (5)	C17—C18—C19—C20	0.5 (2)
C6A—C1A—C7A—C8A	160.1 (3)	C18—C19—C20—C21	−0.2 (2)
C1A—C7A—C8A—C9A	−179.1 (5)	C19—C20—C21—C22	−0.1 (2)
C7A—C8A—C9A—O1A	170.7 (7)	C20—C21—C22—C17	0.1 (2)
C7A—C8A—C9A—O2A	−3.3 (10)	C18—C17—C22—C21	0.2 (2)
C6B—C1B—C2B—C3B	−2.4 (9)	C23—C17—C22—C21	−178.82 (13)
C7B—C1B—C2B—C3B	179.2 (8)	C22—C17—C23—C24	173.26 (14)
C1B—C2B—C3B—C4B	0.5 (10)	C18—C17—C23—C24	−5.7 (2)
C2B—C3B—C4B—C5B	0.6 (12)	C17—C23—C24—C25	−179.87 (12)
C3B—C4B—C5B—C6B	0.4 (13)	C23—C24—C25—O3	179.80 (13)
C2B—C1B—C6B—C5B	3.4 (10)	C23—C24—C25—O4	−0.4 (2)
C7B—C1B—C6B—C5B	−178.2 (9)	N2—C26—C27—C28A	168.44 (16)
C4B—C5B—C6B—C1B	−2.5 (13)	C32—C26—C27—C28A	45.2 (2)
C6B—C1B—C7B—C8B	−12.1 (10)	N2—C26—C27—C28B	84.2 (2)
C2B—C1B—C7B—C8B	166.2 (5)	C32—C26—C27—C28B	−39.0 (2)
C1B—C7B—C8B—C9B	174.8 (10)	C26—C27—C28A—C29	−94.5 (2)
C7B—C8B—C9B—O2B	−4 (2)	C28B—C27—C28A—C29	18.9 (3)
C7B—C8B—C9B—O1B	169.0 (9)	C26—C27—C28B—C29	89.8 (3)
N1—C10—C11—C12A	166.84 (15)	C28A—C27—C28B—C29	−17.7 (2)
C16—C10—C11—C12A	42.7 (2)	C27—C28A—C29—C30	83.8 (3)
N1—C10—C11—C12B	91.5 (7)	C27—C28A—C29—C28B	−18.1 (2)
C16—C10—C11—C12B	−32.6 (8)	C27—C28B—C29—C30	−87.4 (3)
C10—C11—C12A—C13	−85.5 (2)	C27—C28B—C29—C28A	17.1 (2)
C12B—C11—C12A—C13	18.3 (9)	C28A—C29—C30—C31B	4.2 (3)
C10—C11—C12B—C13	94.2 (10)	C28B—C29—C30—C31B	78.5 (3)
C12A—C11—C12B—C13	−16.6 (8)	C28A—C29—C30—C31A	−67.6 (3)
C11—C12A—C13—C14	69.7 (2)	C28B—C29—C30—C31A	6.7 (3)
C11—C12A—C13—C12B	−18.1 (9)	C29—C30—C31A—C32	79.3 (3)
C11—C12B—C13—C14	−98.9 (10)	C31B—C30—C31A—C32	−17.4 (3)
C11—C12B—C13—C12A	16.7 (8)	C29—C30—C31B—C32	−91.8 (3)
C12A—C13—C14—C15A	−54.8 (3)	C31A—C30—C31B—C32	16.9 (3)
C12B—C13—C14—C15A	14.1 (7)	N2—C26—C32—C31A	−88.24 (19)
C12A—C13—C14—C15B	6.8 (5)	C27—C26—C32—C31A	35.2 (2)
C12B—C13—C14—C15B	75.7 (8)	N2—C26—C32—C31B	−163.4 (2)
C13—C14—C15A—C16	72.8 (3)	C27—C26—C32—C31B	−40.0 (2)
C15B—C14—C15A—C16	−29.2 (5)	C30—C31A—C32—C26	−85.7 (2)
C13—C14—C15B—C16	−74.2 (9)	C30—C31A—C32—C31B	16.9 (3)
C15A—C14—C15B—C16	31.1 (6)	C30—C31B—C32—C26	94.8 (3)
C14—C15B—C16—C15A	−30.4 (6)	C30—C31B—C32—C31A	−17.4 (3)
C14—C15B—C16—C10	72.9 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2A	0.98 (2)	1.80 (2)	2.768 (7)	170.7 (17)
N1—H1B···O1A^i	0.96 (2)	1.62 (2)	2.578 (6)	175.6 (19)
N1—H1C···O2A^ii	0.91 (2)	1.95 (2)	2.854 (6)	168.0 (18)
N1—H1A···O1B	0.98 (2)	1.81 (2)	2.775 (9)	172.0 (17)
N1—H1B···O2B^i	0.96 (2)	1.99 (2)	2.945 (9)	170.0 (18)
N1—H1C···O1B^ii	0.91 (2)	1.73 (2)	2.639 (9)	174.4 (19)
N2—H2A···O4	0.953 (18)	1.846 (18)	2.7783 (16)	165.3 (14)
N2—H2B···O4^iii	0.962 (18)	1.867 (18)	2.8205 (16)	170.8 (15)
N2—H2C···O3^i	0.986 (17)	1.745 (17)	2.7277 (16)	174.7 (15)

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

(IV) cyclooctylaminium cinnamate

Crystal data

C8H18N^+·C9H7O2^−	F(000) = 1200
Mr = 275.38	Dx = 1.159 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1345 reflections
a = 24.4790 (4) Å	θ = 3.2–24.5°
b = 6.2800 (4) Å	µ = 0.08 mm^−1
c = 22.6340 (5) Å	T = 173 K
β = 114.894 (2)°	Needle, colourless
V = 3156.2 (2) Å^3	0.55 × 0.03 × 0.02 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer	2044 reflections with I > 2σ(I)
ω scans	Rint = 0.208
Absorption correction: integration (XPREP; Bruker, 2004)	θmax = 23.5°, θmin = 1.8°
Tmin = 0.975, Tmax = 0.999	h = −27→26
15558 measured reflections	k = −7→7
4649 independent reflections	l = −25→25

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.0382P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.160	(Δ/σ)max < 0.001
S = 0.86	Δρmax = 0.26 e Å^−3
4649 reflections	Δρmin = −0.23 e Å^−3
379 parameters

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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
C1A	0.31107 (19)	0.8034 (6)	0.32320 (19)	0.0243 (10)
C2A	0.2570 (2)	0.7036 (7)	0.3143 (2)	0.0353 (12)
H2D	0.2476	0.567	0.2945	0.042*
C3A	0.2174 (2)	0.8041 (8)	0.3344 (2)	0.0427 (13)
H3A	0.1809	0.7358	0.3286	0.051*
C4A	0.2305 (2)	1.0007 (8)	0.3627 (2)	0.0412 (13)
H4A	0.2031	1.0681	0.3764	0.049*
C5A	0.2834 (2)	1.1024 (7)	0.3714 (2)	0.0390 (13)
H5A	0.2922	1.2397	0.3907	0.047*
C6A	0.32375 (19)	1.0021 (7)	0.35155 (19)	0.0296 (11)
H6A	0.3603	1.0713	0.3577	0.036*
C7A	0.35595 (19)	0.6947 (7)	0.30585 (19)	0.0269 (11)
H7A	0.3912	0.7738	0.3126	0.032*
C8A	0.35287 (19)	0.5011 (7)	0.28216 (19)	0.0265 (11)
H8A	0.3169	0.4227	0.2723	0.032*
C9A	0.4020 (2)	0.3945 (7)	0.26949 (19)	0.0261 (11)
O1	0.39404 (13)	0.2077 (5)	0.25205 (14)	0.0347 (8)
O2	0.44773 (13)	0.5089 (5)	0.27742 (13)	0.0312 (8)
C1B	1.18626 (19)	0.5641 (7)	0.5099 (2)	0.0293 (11)
C2B	1.2028 (2)	0.6694 (8)	0.5697 (2)	0.0434 (13)
H2E	1.1881	0.8085	0.5709	0.052*
C3B	1.2407 (2)	0.5701 (11)	0.6268 (2)	0.0616 (18)
H3B	1.2513	0.6405	0.6673	0.074*
C4B	1.2630 (2)	0.3691 (12)	0.6254 (3)	0.077 (2)
H4B	1.2896	0.3032	0.6648	0.092*
C5B	1.2471 (2)	0.2648 (10)	0.5675 (4)	0.070 (2)
H5B	1.2618	0.1254	0.5665	0.084*
C6B	1.2089 (2)	0.3654 (8)	0.5099 (2)	0.0426 (13)
H6B	1.1985	0.2938	0.4696	0.051*
C7B	1.14555 (18)	0.6649 (7)	0.44808 (19)	0.0243 (10)
H7B	1.1347	0.5798	0.4101	0.029*
C8B	1.12274 (18)	0.8542 (7)	0.43898 (19)	0.0263 (11)
H8B	1.1324	0.9417	0.4763	0.032*
C9B	1.08230 (19)	0.9466 (7)	0.3742 (2)	0.0242 (10)
O3	1.06785 (15)	1.1351 (5)	0.37274 (14)	0.0462 (10)
O4	1.06528 (13)	0.8234 (5)	0.32511 (13)	0.0326 (8)
C10A	0.60169 (19)	0.3362 (6)	0.36366 (19)	0.0260 (11)
H10A	0.6434	0.3276	0.3662	0.031*
C11A	0.5996 (2)	0.5331 (7)	0.4015 (2)	0.0361 (12)
H11A	0.557	0.565	0.3914	0.043*
H11B	0.6158	0.6549	0.386	0.043*
C12A	0.6350 (2)	0.5160 (9)	0.4762 (2)	0.0511 (15)
H12A	0.6656	0.4023	0.486	0.061*
H12B	0.6567	0.6517	0.4927	0.061*
C13A	0.5965 (2)	0.4683 (9)	0.5130 (2)	0.0564 (16)
H13A	0.6232	0.4768	0.5601	0.068*
H13B	0.5668	0.5852	0.5033	0.068*
C14A	0.5626 (2)	0.2638 (8)	0.5019 (2)	0.0498 (14)
H14A	0.5448	0.2551	0.5338	0.06*
H14B	0.5918	0.1456	0.5115	0.06*
C15A	0.5120 (2)	0.2265 (8)	0.4337 (2)	0.0444 (14)
H15A	0.4776	0.1596	0.4388	0.053*
H15B	0.4982	0.3667	0.4127	0.053*
C16A	0.5281 (2)	0.0889 (7)	0.3882 (2)	0.0366 (12)
H16A	0.4964	0.1088	0.3436	0.044*
H16B	0.5263	−0.0618	0.4002	0.044*
C17A	0.5887 (2)	0.1243 (7)	0.3860 (2)	0.0376 (12)
H17A	0.6204	0.0983	0.4304	0.045*
H17B	0.5934	0.0137	0.3573	0.045*
N1	0.56005 (17)	0.3735 (7)	0.29309 (18)	0.0250 (10)
H1A	0.529 (2)	0.396 (7)	0.293 (2)	0.038*
H1B	0.5565 (18)	0.235 (7)	0.2673 (19)	0.038*
H1C	0.5805 (19)	0.508 (6)	0.2806 (19)	0.038*
C10B	0.94705 (19)	0.5136 (6)	0.32230 (18)	0.0227 (10)
H10B	0.9184	0.3907	0.3106	0.027*
C11B	0.97645 (18)	0.5310 (7)	0.39612 (18)	0.0238 (10)
H11C	1.0038	0.6554	0.4085	0.029*
H11D	1.0013	0.4024	0.4142	0.029*
C12B	0.93154 (19)	0.5548 (6)	0.42769 (19)	0.0273 (11)
H12C	0.8914	0.5059	0.3961	0.033*
H12D	0.9445	0.46	0.4661	0.033*
C13B	0.9256 (2)	0.7800 (6)	0.4490 (2)	0.0304 (11)
H13C	0.8912	0.7827	0.4612	0.037*
H13D	0.9623	0.8129	0.4887	0.037*
C14B	0.91641 (19)	0.9564 (7)	0.3999 (2)	0.0314 (11)
H14C	0.9517	0.9575	0.3892	0.038*
H14D	0.9162	1.0939	0.4212	0.038*
C15B	0.8598 (2)	0.9464 (7)	0.3362 (2)	0.0337 (12)
H15C	0.8245	0.9416	0.3469	0.04*
H15D	0.8571	1.0805	0.3121	0.04*
C16B	0.85456 (19)	0.7615 (7)	0.2906 (2)	0.0333 (12)
H16C	0.8226	0.7958	0.2471	0.04*
H16D	0.8413	0.6339	0.3067	0.04*
C17B	0.91276 (19)	0.7044 (7)	0.28281 (19)	0.0294 (11)
H17C	0.902	0.6759	0.2362	0.035*
H17D	0.9399	0.8296	0.2956	0.035*
N2	0.99557 (16)	0.4593 (6)	0.30078 (17)	0.0225 (9)
H2A	1.0258 (19)	0.588 (6)	0.3114 (18)	0.034*
H2B	0.9822 (19)	0.429 (6)	0.259 (2)	0.034*
H2C	1.0217 (18)	0.317 (6)	0.3255 (18)	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.022 (3)	0.028 (3)	0.022 (2)	−0.003 (2)	0.009 (2)	−0.001 (2)
C2A	0.028 (3)	0.035 (3)	0.047 (3)	−0.003 (2)	0.020 (2)	−0.010 (2)
C3A	0.029 (3)	0.056 (4)	0.052 (3)	−0.001 (3)	0.026 (3)	−0.004 (3)
C4A	0.039 (3)	0.054 (4)	0.036 (3)	0.006 (3)	0.022 (2)	−0.008 (3)
C5A	0.040 (3)	0.043 (3)	0.033 (3)	0.004 (3)	0.014 (2)	−0.012 (2)
C6A	0.021 (3)	0.035 (3)	0.030 (3)	−0.002 (2)	0.008 (2)	−0.004 (2)
C7A	0.022 (3)	0.035 (3)	0.029 (3)	−0.003 (2)	0.016 (2)	0.001 (2)
C8A	0.023 (3)	0.033 (3)	0.029 (3)	−0.005 (2)	0.017 (2)	0.000 (2)
C9A	0.023 (3)	0.035 (3)	0.021 (3)	0.005 (2)	0.010 (2)	0.002 (2)
O1	0.0301 (19)	0.039 (2)	0.0389 (19)	0.0005 (16)	0.0180 (15)	−0.0121 (16)
O2	0.0260 (19)	0.0368 (19)	0.0387 (19)	0.0053 (17)	0.0214 (15)	0.0085 (15)
C1B	0.018 (3)	0.037 (3)	0.034 (3)	0.003 (2)	0.012 (2)	0.013 (2)
C2B	0.025 (3)	0.067 (4)	0.033 (3)	−0.003 (3)	0.007 (2)	0.013 (3)
C3B	0.028 (3)	0.115 (5)	0.032 (3)	−0.015 (4)	0.003 (3)	0.026 (3)
C4B	0.019 (3)	0.117 (6)	0.079 (5)	0.005 (4)	0.005 (3)	0.070 (5)
C5B	0.027 (3)	0.066 (4)	0.112 (6)	0.012 (3)	0.023 (4)	0.056 (4)
C6B	0.025 (3)	0.042 (3)	0.059 (4)	0.000 (3)	0.016 (3)	0.022 (3)
C7B	0.018 (2)	0.034 (3)	0.020 (2)	0.000 (2)	0.0076 (19)	0.002 (2)
C8B	0.019 (3)	0.036 (3)	0.021 (2)	0.003 (2)	0.006 (2)	0.001 (2)
C9B	0.016 (2)	0.032 (3)	0.028 (3)	0.001 (2)	0.012 (2)	0.005 (2)
O3	0.058 (3)	0.039 (2)	0.037 (2)	0.0253 (19)	0.0158 (18)	0.0113 (16)
O4	0.033 (2)	0.042 (2)	0.0186 (17)	−0.0059 (16)	0.0066 (14)	0.0060 (16)
C10A	0.024 (3)	0.030 (3)	0.026 (3)	−0.001 (2)	0.012 (2)	0.006 (2)
C11A	0.033 (3)	0.042 (3)	0.032 (3)	−0.006 (2)	0.013 (2)	0.002 (2)
C12A	0.037 (3)	0.074 (4)	0.036 (3)	−0.016 (3)	0.009 (3)	−0.007 (3)
C13A	0.057 (4)	0.091 (4)	0.021 (3)	−0.022 (4)	0.016 (3)	−0.009 (3)
C14A	0.041 (3)	0.079 (4)	0.031 (3)	−0.009 (3)	0.017 (2)	0.002 (3)
C15A	0.030 (3)	0.067 (4)	0.037 (3)	−0.010 (3)	0.016 (2)	−0.001 (3)
C16A	0.030 (3)	0.042 (3)	0.036 (3)	−0.005 (2)	0.013 (2)	0.007 (2)
C17A	0.038 (3)	0.041 (3)	0.034 (3)	0.005 (3)	0.016 (2)	0.006 (2)
N1	0.019 (2)	0.032 (2)	0.029 (2)	0.001 (2)	0.0153 (19)	0.0000 (18)
C10B	0.020 (2)	0.027 (3)	0.023 (2)	0.000 (2)	0.012 (2)	−0.003 (2)
C11B	0.019 (2)	0.030 (3)	0.021 (2)	0.000 (2)	0.0068 (19)	0.003 (2)
C12B	0.027 (3)	0.036 (3)	0.021 (2)	−0.002 (2)	0.013 (2)	0.002 (2)
C13B	0.035 (3)	0.030 (3)	0.035 (3)	0.000 (2)	0.023 (2)	−0.006 (2)
C14B	0.028 (3)	0.034 (3)	0.037 (3)	−0.001 (2)	0.017 (2)	−0.007 (2)
C15B	0.028 (3)	0.036 (3)	0.042 (3)	0.005 (2)	0.018 (2)	−0.001 (2)
C16B	0.026 (3)	0.037 (3)	0.034 (3)	0.012 (2)	0.009 (2)	0.003 (2)
C17B	0.028 (3)	0.037 (3)	0.020 (2)	0.011 (2)	0.008 (2)	0.000 (2)
N2	0.026 (2)	0.031 (2)	0.0138 (19)	−0.0002 (19)	0.0120 (17)	−0.0030 (18)

Geometric parameters (Å, º)

C1A—C6A	1.377 (5)	C12A—H12B	0.99
C1A—C2A	1.400 (6)	C13A—C14A	1.492 (6)
C1A—C7A	1.480 (6)	C13A—H13A	0.99
C2A—C3A	1.386 (6)	C13A—H13B	0.99
C2A—H2D	0.95	C14A—C15A	1.536 (6)
C3A—C4A	1.365 (6)	C14A—H14A	0.99
C3A—H3A	0.95	C14A—H14B	0.99
C4A—C5A	1.380 (6)	C15A—C16A	1.518 (6)
C4A—H4A	0.95	C15A—H15A	0.99
C5A—C6A	1.396 (6)	C15A—H15B	0.99
C5A—H5A	0.95	C16A—C17A	1.522 (6)
C6A—H6A	0.95	C16A—H16A	0.99
C7A—C8A	1.318 (5)	C16A—H16B	0.99
C7A—H7A	0.95	C17A—H17A	0.99
C8A—C9A	1.506 (6)	C17A—H17B	0.99
C8A—H8A	0.95	N1—H1A	0.78 (5)
C9A—O1	1.227 (5)	N1—H1B	1.03 (4)
C9A—O2	1.277 (5)	N1—H1C	1.08 (4)
C1B—C6B	1.366 (6)	C10B—N2	1.500 (5)
C1B—C2B	1.404 (6)	C10B—C17B	1.519 (5)
C1B—C7B	1.476 (6)	C10B—C11B	1.520 (5)
C2B—C3B	1.383 (6)	C10B—H10B	1
C2B—H2E	0.95	C11B—C12B	1.550 (5)
C3B—C4B	1.381 (8)	C11B—H11C	0.99
C3B—H3B	0.95	C11B—H11D	0.99
C4B—C5B	1.367 (8)	C12B—C13B	1.521 (5)
C4B—H4B	0.95	C12B—H12C	0.99
C5B—C6B	1.396 (7)	C12B—H12D	0.99
C5B—H5B	0.95	C13B—C14B	1.518 (5)
C6B—H6B	0.95	C13B—H13C	0.99
C7B—C8B	1.292 (5)	C13B—H13D	0.99
C7B—H7B	0.95	C14B—C15B	1.523 (6)
C8B—C9B	1.498 (6)	C14B—H14C	0.99
C8B—H8B	0.95	C14B—H14D	0.99
C9B—O3	1.232 (5)	C15B—C16B	1.522 (6)
C9B—O4	1.272 (5)	C15B—H15C	0.99
C10A—C17A	1.504 (5)	C15B—H15D	0.99
C10A—N1	1.508 (5)	C16B—C17B	1.550 (6)
C10A—C11A	1.517 (6)	C16B—H16C	0.99
C10A—H10A	1	C16B—H16D	0.99
C11A—C12A	1.545 (6)	C17B—H17C	0.99
C11A—H11A	0.99	C17B—H17D	0.99
C11A—H11B	0.99	N2—H2A	1.05 (4)
C12A—C13A	1.527 (6)	N2—H2B	0.88 (4)
C12A—H12A	0.99	N2—H2C	1.11 (4)
C6A—C1A—C2A	119.1 (4)	C13A—C14A—H14B	108
C6A—C1A—C7A	119.7 (4)	C15A—C14A—H14B	108
C2A—C1A—C7A	121.1 (4)	H14A—C14A—H14B	107.2
C3A—C2A—C1A	119.9 (4)	C16A—C15A—C14A	116.0 (4)
C3A—C2A—H2D	120	C16A—C15A—H15A	108.3
C1A—C2A—H2D	120	C14A—C15A—H15A	108.3
C4A—C3A—C2A	120.4 (5)	C16A—C15A—H15B	108.3
C4A—C3A—H3A	119.8	C14A—C15A—H15B	108.3
C2A—C3A—H3A	119.8	H15A—C15A—H15B	107.4
C3A—C4A—C5A	120.5 (5)	C15A—C16A—C17A	118.3 (4)
C3A—C4A—H4A	119.8	C15A—C16A—H16A	107.7
C5A—C4A—H4A	119.8	C17A—C16A—H16A	107.7
C4A—C5A—C6A	119.5 (4)	C15A—C16A—H16B	107.7
C4A—C5A—H5A	120.2	C17A—C16A—H16B	107.7
C6A—C5A—H5A	120.2	H16A—C16A—H16B	107.1
C1A—C6A—C5A	120.5 (4)	C10A—C17A—C16A	119.1 (4)
C1A—C6A—H6A	119.7	C10A—C17A—H17A	107.5
C5A—C6A—H6A	119.7	C16A—C17A—H17A	107.5
C8A—C7A—C1A	127.7 (4)	C10A—C17A—H17B	107.5
C8A—C7A—H7A	116.1	C16A—C17A—H17B	107.5
C1A—C7A—H7A	116.1	H17A—C17A—H17B	107
C7A—C8A—C9A	125.0 (4)	C10A—N1—H1A	105 (3)
C7A—C8A—H8A	117.5	C10A—N1—H1B	109 (2)
C9A—C8A—H8A	117.5	H1A—N1—H1B	107 (4)
O1—C9A—O2	126.5 (4)	C10A—N1—H1C	103 (2)
O1—C9A—C8A	117.0 (4)	H1A—N1—H1C	115 (4)
O2—C9A—C8A	116.5 (4)	H1B—N1—H1C	117 (3)
C6B—C1B—C2B	118.6 (4)	N2—C10B—C17B	107.7 (3)
C6B—C1B—C7B	120.2 (4)	N2—C10B—C11B	107.5 (3)
C2B—C1B—C7B	121.2 (4)	C17B—C10B—C11B	118.6 (3)
C3B—C2B—C1B	119.8 (5)	N2—C10B—H10B	107.5
C3B—C2B—H2E	120.1	C17B—C10B—H10B	107.5
C1B—C2B—H2E	120.1	C11B—C10B—H10B	107.5
C4B—C3B—C2B	120.4 (6)	C10B—C11B—C12B	114.5 (3)
C4B—C3B—H3B	119.8	C10B—C11B—H11C	108.6
C2B—C3B—H3B	119.8	C12B—C11B—H11C	108.6
C5B—C4B—C3B	120.3 (6)	C10B—C11B—H11D	108.6
C5B—C4B—H4B	119.9	C12B—C11B—H11D	108.6
C3B—C4B—H4B	119.9	H11C—C11B—H11D	107.6
C4B—C5B—C6B	119.2 (6)	C13B—C12B—C11B	114.7 (3)
C4B—C5B—H5B	120.4	C13B—C12B—H12C	108.6
C6B—C5B—H5B	120.4	C11B—C12B—H12C	108.6
C1B—C6B—C5B	121.6 (6)	C13B—C12B—H12D	108.6
C1B—C6B—H6B	119.2	C11B—C12B—H12D	108.6
C5B—C6B—H6B	119.2	H12C—C12B—H12D	107.6
C8B—C7B—C1B	128.3 (4)	C14B—C13B—C12B	116.8 (3)
C8B—C7B—H7B	115.9	C14B—C13B—H13C	108.1
C1B—C7B—H7B	115.9	C12B—C13B—H13C	108.1
C7B—C8B—C9B	125.1 (4)	C14B—C13B—H13D	108.1
C7B—C8B—H8B	117.4	C12B—C13B—H13D	108.1
C9B—C8B—H8B	117.4	H13C—C13B—H13D	107.3
O3—C9B—O4	125.2 (4)	C13B—C14B—C15B	117.3 (4)
O3—C9B—C8B	117.5 (4)	C13B—C14B—H14C	108
O4—C9B—C8B	117.3 (4)	C15B—C14B—H14C	108
C17A—C10A—N1	110.4 (3)	C13B—C14B—H14D	108
C17A—C10A—C11A	118.0 (4)	C15B—C14B—H14D	108
N1—C10A—C11A	107.7 (3)	H14C—C14B—H14D	107.2
C17A—C10A—H10A	106.7	C16B—C15B—C14B	117.1 (4)
N1—C10A—H10A	106.7	C16B—C15B—H15C	108
C11A—C10A—H10A	106.7	C14B—C15B—H15C	108
C10A—C11A—C12A	115.1 (4)	C16B—C15B—H15D	108
C10A—C11A—H11A	108.5	C14B—C15B—H15D	108
C12A—C11A—H11A	108.5	H15C—C15B—H15D	107.3
C10A—C11A—H11B	108.5	C15B—C16B—C17B	115.8 (4)
C12A—C11A—H11B	108.5	C15B—C16B—H16C	108.3
H11A—C11A—H11B	107.5	C17B—C16B—H16C	108.3
C13A—C12A—C11A	114.9 (4)	C15B—C16B—H16D	108.3
C13A—C12A—H12A	108.6	C17B—C16B—H16D	108.3
C11A—C12A—H12A	108.6	H16C—C16B—H16D	107.4
C13A—C12A—H12B	108.6	C10B—C17B—C16B	115.0 (4)
C11A—C12A—H12B	108.6	C10B—C17B—H17C	108.5
H12A—C12A—H12B	107.5	C16B—C17B—H17C	108.5
C14A—C13A—C12A	120.3 (4)	C10B—C17B—H17D	108.5
C14A—C13A—H13A	107.3	C16B—C17B—H17D	108.5
C12A—C13A—H13A	107.3	H17C—C17B—H17D	107.5
C14A—C13A—H13B	107.3	C10B—N2—H2A	109 (2)
C12A—C13A—H13B	107.3	C10B—N2—H2B	114 (3)
H13A—C13A—H13B	106.9	H2A—N2—H2B	109 (3)
C13A—C14A—C15A	117.2 (4)	C10B—N2—H2C	113 (2)
C13A—C14A—H14A	108	H2A—N2—H2C	108 (3)
C15A—C14A—H14A	108	H2B—N2—H2C	104 (3)
C6A—C1A—C2A—C3A	−0.5 (6)	C1B—C7B—C8B—C9B	179.0 (4)
C7A—C1A—C2A—C3A	176.3 (4)	C7B—C8B—C9B—O3	−174.5 (4)
C1A—C2A—C3A—C4A	0.3 (7)	C7B—C8B—C9B—O4	5.9 (6)
C2A—C3A—C4A—C5A	0.2 (7)	C17A—C10A—C11A—C12A	48.6 (6)
C3A—C4A—C5A—C6A	−0.5 (7)	N1—C10A—C11A—C12A	174.4 (4)
C2A—C1A—C6A—C5A	0.2 (6)	C10A—C11A—C12A—C13A	−100.1 (5)
C7A—C1A—C6A—C5A	−176.6 (4)	C11A—C12A—C13A—C14A	63.3 (7)
C4A—C5A—C6A—C1A	0.3 (6)	C12A—C13A—C14A—C15A	−64.8 (7)
C6A—C1A—C7A—C8A	175.7 (4)	C13A—C14A—C15A—C16A	98.6 (5)
C2A—C1A—C7A—C8A	−1.1 (7)	C14A—C15A—C16A—C17A	−42.6 (6)
C1A—C7A—C8A—C9A	−175.9 (4)	N1—C10A—C17A—C16A	−64.9 (5)
C7A—C8A—C9A—O1	174.5 (4)	C11A—C10A—C17A—C16A	59.4 (6)
C7A—C8A—C9A—O2	−6.1 (6)	C15A—C16A—C17A—C10A	−62.6 (6)
C6B—C1B—C2B—C3B	−0.9 (6)	N2—C10B—C11B—C12B	−171.7 (3)
C7B—C1B—C2B—C3B	179.5 (4)	C17B—C10B—C11B—C12B	65.9 (5)
C1B—C2B—C3B—C4B	1.0 (7)	C10B—C11B—C12B—C13B	−102.5 (4)
C2B—C3B—C4B—C5B	−1.2 (8)	C11B—C12B—C13B—C14B	48.2 (5)
C3B—C4B—C5B—C6B	1.3 (9)	C12B—C13B—C14B—C15B	61.8 (5)
C2B—C1B—C6B—C5B	1.0 (7)	C13B—C14B—C15B—C16B	−65.7 (5)
C7B—C1B—C6B—C5B	−179.4 (4)	C14B—C15B—C16B—C17B	−42.1 (6)
C4B—C5B—C6B—C1B	−1.2 (8)	N2—C10B—C17B—C16B	170.8 (3)
C6B—C1B—C7B—C8B	−176.1 (5)	C11B—C10B—C17B—C16B	−67.0 (5)
C2B—C1B—C7B—C8B	3.5 (7)	C15B—C16B—C17B—C10B	100.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.78 (5)	1.99 (5)	2.755 (5)	166 (5)
N1—H1B···O2^i	1.03 (4)	1.72 (4)	2.751 (5)	177 (4)
N1—H1C···O1^ii	1.08 (4)	1.70 (4)	2.771 (5)	171 (3)
N2—H2A···O4	1.05 (4)	1.72 (4)	2.766 (5)	171 (3)
N2—H2B···O4^iii	0.88 (4)	1.89 (4)	2.737 (4)	163 (4)
N2—H2C···O3^iv	1.11 (4)	1.64 (4)	2.739 (5)	170 (3)

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

(V) cyclododecylaminium cinnamate

Crystal data

C12H26N^+·C9H7O2^−	F(000) = 364
Mr = 331.48	Dx = 1.095 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2656 reflections
a = 12.6990 (4) Å	θ = 2.7–27.8°
b = 5.8910 (2) Å	µ = 0.07 mm^−1
c = 14.387 (4) Å	T = 173 K
β = 110.855 (2)°	Needle, colourless
V = 1005.8 (3) Å^3	0.59 × 0.11 × 0.07 mm
Z = 2

Data collection

Bruker APEXII CCD area-detector diffractometer	2137 reflections with I > 2σ(I)
ω scans	Rint = 0.096
Absorption correction: integration (XPREP; Bruker, 2004)	θmax = 28°, θmin = 1.5°
Tmin = 0.969, Tmax = 0.996	h = −15→16
7908 measured reflections	k = −7→7
2665 independent reflections	l = −19→13

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0647P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.124	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.19 e Å^−3
2665 reflections	Δρmin = −0.24 e Å^−3
226 parameters

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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
C1	0.62139 (18)	0.4237 (4)	0.12516 (17)	0.0292 (5)
C2	0.6688 (2)	0.6340 (5)	0.15644 (19)	0.0383 (6)
H2	0.676	0.6874	0.2207	0.046*
C3	0.7059 (2)	0.7674 (5)	0.0953 (2)	0.0473 (7)
H3	0.7393	0.9109	0.118	0.057*
C4	0.6943 (2)	0.6924 (5)	0.0013 (2)	0.0499 (8)
H4	0.7196	0.7847	−0.0407	0.06*
C5	0.6466 (2)	0.4855 (5)	−0.0314 (2)	0.0436 (6)
H5	0.638	0.4352	−0.0965	0.052*
C6	0.6109 (2)	0.3490 (5)	0.03008 (18)	0.0339 (5)
H6	0.5792	0.2042	0.0075	0.041*
C7	0.58025 (18)	0.2740 (4)	0.18712 (16)	0.0294 (5)
H7	0.5757	0.1165	0.1721	0.035*
C8	0.5490 (2)	0.3379 (4)	0.26163 (18)	0.0320 (5)
H8	0.5535	0.4937	0.2797	0.038*
C9	0.50710 (19)	0.1703 (4)	0.31749 (16)	0.0295 (5)
O1	0.46560 (15)	0.2514 (3)	0.37969 (11)	0.0330 (4)
O2	0.51311 (16)	−0.0360 (3)	0.30313 (13)	0.0393 (4)
C10	0.3110 (2)	0.7431 (4)	0.40472 (17)	0.0331 (5)
H10	0.3106	0.877	0.4473	0.04*
C11	0.2438 (2)	0.8062 (4)	0.29675 (18)	0.0387 (6)
H11A	0.1644	0.8316	0.2901	0.046*
H11B	0.2733	0.9518	0.2817	0.046*
C12	0.2460 (2)	0.6322 (5)	0.21905 (18)	0.0391 (6)
H12A	0.2477	0.4776	0.2465	0.047*
H12B	0.3156	0.653	0.2039	0.047*
C13	0.1430 (2)	0.6545 (6)	0.12251 (19)	0.0460 (7)
H13A	0.1352	0.8152	0.1009	0.055*
H13B	0.1562	0.5633	0.0699	0.055*
C14	0.0334 (2)	0.5774 (5)	0.13299 (19)	0.0462 (7)
H14A	0.0238	0.66	0.1894	0.055*
H14B	−0.03	0.6209	0.072	0.055*
C15	0.0260 (2)	0.3253 (5)	0.1498 (2)	0.0493 (7)
H15A	0.0987	0.2744	0.1992	0.059*
H15B	0.0154	0.2452	0.0866	0.059*
C16	−0.0678 (2)	0.2544 (6)	0.1859 (2)	0.0604 (8)
H16A	−0.0729	0.0867	0.1845	0.073*
H16B	−0.1402	0.3142	0.1391	0.073*
C17	−0.0522 (2)	0.3361 (6)	0.2901 (2)	0.0569 (8)
H17A	−0.1218	0.3034	0.3037	0.068*
H17B	−0.0416	0.5028	0.2928	0.068*
C18	0.0472 (2)	0.2279 (5)	0.3711 (2)	0.0483 (7)
H18A	0.1087	0.2048	0.345	0.058*
H18B	0.0239	0.0765	0.3866	0.058*
C19	0.0932 (3)	0.3640 (6)	0.4673 (2)	0.0557 (8)
H19A	0.1462	0.2674	0.5193	0.067*
H19B	0.0299	0.4033	0.4893	0.067*
C20	0.1536 (3)	0.5818 (5)	0.4581 (2)	0.0534 (8)
H20A	0.1674	0.6746	0.5187	0.064*
H20B	0.104	0.6703	0.4007	0.064*
C21	0.2657 (2)	0.5384 (5)	0.44432 (19)	0.0394 (6)
H21A	0.2562	0.41	0.3977	0.047*
H21B	0.3223	0.4928	0.5091	0.047*
N1	0.43084 (17)	0.6962 (3)	0.41541 (15)	0.0289 (4)
H1A	0.439 (2)	0.549 (5)	0.395 (2)	0.043*
H1B	0.470 (2)	0.697 (5)	0.474 (2)	0.043*
H1C	0.465 (2)	0.798 (5)	0.382 (2)	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0284 (10)	0.0317 (12)	0.0293 (12)	0.0028 (10)	0.0125 (9)	0.0059 (10)
C2	0.0373 (12)	0.0372 (13)	0.0414 (14)	−0.0022 (11)	0.0153 (11)	0.0016 (11)
C3	0.0406 (13)	0.0341 (13)	0.0669 (19)	−0.0032 (12)	0.0189 (13)	0.0095 (14)
C4	0.0450 (14)	0.0543 (18)	0.0603 (18)	0.0065 (14)	0.0308 (14)	0.0280 (15)
C5	0.0450 (14)	0.0553 (16)	0.0370 (13)	0.0126 (14)	0.0226 (12)	0.0118 (13)
C6	0.0358 (11)	0.0353 (12)	0.0327 (12)	0.0051 (11)	0.0148 (10)	0.0069 (10)
C7	0.0346 (11)	0.0251 (11)	0.0285 (11)	−0.0013 (9)	0.0111 (10)	−0.0007 (10)
C8	0.0425 (12)	0.0241 (10)	0.0314 (12)	−0.0044 (10)	0.0155 (10)	−0.0011 (10)
C9	0.0371 (11)	0.0283 (12)	0.0239 (11)	−0.0027 (10)	0.0119 (9)	0.0019 (9)
O1	0.0494 (9)	0.0282 (8)	0.0253 (8)	0.0025 (8)	0.0180 (7)	0.0002 (7)
O2	0.0653 (11)	0.0247 (9)	0.0382 (10)	−0.0033 (8)	0.0309 (9)	−0.0010 (7)
C10	0.0414 (12)	0.0279 (11)	0.0313 (12)	0.0032 (11)	0.0145 (10)	−0.0041 (10)
C11	0.0408 (12)	0.0366 (15)	0.0375 (13)	0.0053 (11)	0.0123 (11)	0.0041 (11)
C12	0.0372 (12)	0.0487 (15)	0.0313 (12)	0.0067 (11)	0.0121 (11)	0.0007 (11)
C13	0.0442 (14)	0.0619 (18)	0.0299 (12)	0.0089 (14)	0.0108 (11)	0.0059 (13)
C14	0.0388 (13)	0.0593 (17)	0.0341 (14)	0.0092 (13)	0.0050 (11)	0.0055 (13)
C15	0.0448 (14)	0.0561 (18)	0.0397 (15)	0.0014 (14)	0.0061 (12)	−0.0111 (13)
C16	0.0407 (14)	0.062 (2)	0.069 (2)	−0.0059 (15)	0.0070 (14)	0.0035 (18)
C17	0.0387 (14)	0.0613 (19)	0.078 (2)	0.0062 (14)	0.0293 (15)	0.0169 (17)
C18	0.0493 (15)	0.0417 (15)	0.0599 (17)	0.0030 (13)	0.0267 (14)	0.0093 (14)
C19	0.0653 (19)	0.0599 (18)	0.0616 (19)	0.0009 (17)	0.0466 (17)	0.0055 (16)
C20	0.0605 (18)	0.0539 (17)	0.0608 (18)	−0.0038 (15)	0.0401 (16)	−0.0113 (16)
C21	0.0456 (14)	0.0427 (15)	0.0344 (13)	−0.0017 (12)	0.0197 (12)	−0.0021 (11)
N1	0.0391 (10)	0.0238 (10)	0.0236 (9)	−0.0010 (8)	0.0109 (8)	0.0001 (8)

Geometric parameters (Å, º)

C1—C2	1.381 (3)	C13—H13A	0.99
C1—C6	1.397 (3)	C13—H13B	0.99
C1—C7	1.475 (3)	C14—C15	1.513 (4)
C2—C3	1.381 (4)	C14—H14A	0.99
C2—H2	0.95	C14—H14B	0.99
C3—C4	1.380 (4)	C15—C16	1.517 (4)
C3—H3	0.95	C15—H15A	0.99
C4—C5	1.368 (4)	C15—H15B	0.99
C4—H4	0.95	C16—C17	1.519 (5)
C5—C6	1.386 (3)	C16—H16A	0.99
C5—H5	0.95	C16—H16B	0.99
C6—H6	0.95	C17—C18	1.520 (4)
C7—C8	1.323 (3)	C17—H17A	0.99
C7—H7	0.95	C17—H17B	0.99
C8—C9	1.486 (3)	C18—C19	1.524 (4)
C8—H8	0.95	C18—H18A	0.99
C9—O2	1.240 (3)	C18—H18B	0.99
C9—O1	1.282 (3)	C19—C20	1.525 (4)
C10—N1	1.500 (3)	C19—H19A	0.99
C10—C11	1.528 (3)	C19—H19B	0.99
C10—C21	1.530 (3)	C20—C21	1.528 (4)
C10—H10	1	C20—H20A	0.99
C11—C12	1.524 (3)	C20—H20B	0.99
C11—H11A	0.99	C21—H21A	0.99
C11—H11B	0.99	C21—H21B	0.99
C12—C13	1.537 (4)	N1—H1A	0.93 (3)
C12—H12A	0.99	N1—H1B	0.81 (3)
C12—H12B	0.99	N1—H1C	0.96 (3)
C13—C14	1.522 (4)
C2—C1—C6	118.7 (2)	C13—C14—H14A	108.6
C2—C1—C7	123.1 (2)	C15—C14—H14B	108.6
C6—C1—C7	118.2 (2)	C13—C14—H14B	108.6
C1—C2—C3	120.7 (2)	H14A—C14—H14B	107.5
C1—C2—H2	119.6	C14—C15—C16	115.2 (3)
C3—C2—H2	119.6	C14—C15—H15A	108.5
C4—C3—C2	120.0 (3)	C16—C15—H15A	108.5
C4—C3—H3	120	C14—C15—H15B	108.5
C2—C3—H3	120	C16—C15—H15B	108.5
C5—C4—C3	120.1 (2)	H15A—C15—H15B	107.5
C5—C4—H4	119.9	C15—C16—C17	114.1 (3)
C3—C4—H4	119.9	C15—C16—H16A	108.7
C4—C5—C6	120.2 (3)	C17—C16—H16A	108.7
C4—C5—H5	119.9	C15—C16—H16B	108.7
C6—C5—H5	119.9	C17—C16—H16B	108.7
C5—C6—C1	120.2 (2)	H16A—C16—H16B	107.6
C5—C6—H6	119.9	C16—C17—C18	113.9 (3)
C1—C6—H6	119.9	C16—C17—H17A	108.8
C8—C7—C1	126.3 (2)	C18—C17—H17A	108.8
C8—C7—H7	116.8	C16—C17—H17B	108.8
C1—C7—H7	116.8	C18—C17—H17B	108.8
C7—C8—C9	121.2 (2)	H17A—C17—H17B	107.7
C7—C8—H8	119.4	C17—C18—C19	114.9 (3)
C9—C8—H8	119.4	C17—C18—H18A	108.5
O2—C9—O1	123.1 (2)	C19—C18—H18A	108.5
O2—C9—C8	120.4 (2)	C17—C18—H18B	108.5
O1—C9—C8	116.5 (2)	C19—C18—H18B	108.5
N1—C10—C11	109.14 (18)	H18A—C18—H18B	107.5
N1—C10—C21	108.57 (19)	C18—C19—C20	113.9 (2)
C11—C10—C21	115.0 (2)	C18—C19—H19A	108.8
N1—C10—H10	108	C20—C19—H19A	108.8
C11—C10—H10	108	C18—C19—H19B	108.8
C21—C10—H10	108	C20—C19—H19B	108.8
C12—C11—C10	115.6 (2)	H19A—C19—H19B	107.7
C12—C11—H11A	108.4	C19—C20—C21	113.1 (2)
C10—C11—H11A	108.4	C19—C20—H20A	109
C12—C11—H11B	108.4	C21—C20—H20A	109
C10—C11—H11B	108.4	C19—C20—H20B	109
H11A—C11—H11B	107.4	C21—C20—H20B	109
C11—C12—C13	111.9 (2)	H20A—C20—H20B	107.8
C11—C12—H12A	109.2	C20—C21—C10	114.0 (2)
C13—C12—H12A	109.2	C20—C21—H21A	108.7
C11—C12—H12B	109.2	C10—C21—H21A	108.7
C13—C12—H12B	109.2	C20—C21—H21B	108.7
H12A—C12—H12B	107.9	C10—C21—H21B	108.7
C14—C13—C12	113.5 (2)	H21A—C21—H21B	107.6
C14—C13—H13A	108.9	C10—N1—H1A	111.1 (17)
C12—C13—H13A	108.9	C10—N1—H1B	110 (2)
C14—C13—H13B	108.9	H1A—N1—H1B	103 (3)
C12—C13—H13B	108.9	C10—N1—H1C	117.2 (17)
H13A—C13—H13B	107.7	H1A—N1—H1C	108 (2)
C15—C14—C13	114.8 (2)	H1B—N1—H1C	107 (3)
C15—C14—H14A	108.6
C6—C1—C2—C3	−0.4 (3)	C21—C10—C11—C12	−66.0 (3)
C7—C1—C2—C3	−179.9 (2)	C10—C11—C12—C13	156.2 (2)
C1—C2—C3—C4	0.9 (4)	C11—C12—C13—C14	−71.0 (3)
C2—C3—C4—C5	−0.3 (4)	C12—C13—C14—C15	−67.8 (3)
C3—C4—C5—C6	−0.8 (4)	C13—C14—C15—C16	165.3 (2)
C4—C5—C6—C1	1.2 (4)	C14—C15—C16—C17	−67.2 (4)
C2—C1—C6—C5	−0.6 (3)	C15—C16—C17—C18	−67.0 (4)
C7—C1—C6—C5	178.9 (2)	C16—C17—C18—C19	157.4 (3)
C2—C1—C7—C8	23.0 (4)	C17—C18—C19—C20	−69.9 (3)
C6—C1—C7—C8	−156.5 (2)	C18—C19—C20—C21	−69.7 (4)
C1—C7—C8—C9	179.0 (2)	C19—C20—C21—C10	162.9 (2)
C7—C8—C9—O2	8.6 (4)	N1—C10—C21—C20	167.9 (2)
C7—C8—C9—O1	−171.4 (2)	C11—C10—C21—C20	−69.5 (3)
N1—C10—C11—C12	56.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.93 (3)	1.81 (3)	2.736 (3)	170 (3)
N1—H1B···O1^i	0.81 (3)	2.00 (3)	2.786 (3)	165 (3)
N1—H1C···O2^ii	0.96 (3)	1.77 (3)	2.719 (2)	170 (3)

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