Chains of fused rings in the hydrogen-bonded structure of meso-­6,13-di­amino-6,13-di­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane–2,2′-biphenol (1/2)

The title compound is a salt, [C₁₂H₃₂N₆]²⁺·2[HOC₆H₄C₆H₄O]⁻. The centrosymmetric cation contains two intramolecular N—H...N hydrogen bonds with an N...N distance of 2.8290 (13) Å, and the pendent amino groups are in axial sites; the anion contains an intramolecular O—H...O hydrogen bond with an O...O distance of 2.4656 (11) Å. The ions are linked into continuous chains by means of four types of N—H...O hydrogen bonds with N...O distances ranging from 2.7238 (12) Å to 3.3091 (13) Å, associated with N—H...O angles in the range 148–160°.

S1. Comment

The simple macrocyclic tetra-amine 1,4,8,11-tetraazacyclotetradecane [cyclam, C₁₀H₂₄N₄, (I)] forms a 1:2 salt-type adduct with 2,2'-biphenol in which all four of its axial N—H bonds participate in intermolecular hydrogen bonding, so that the supramolecular structure consists of chains of fused R²₂(10) and R⁴₆(12) rings (Ferguson et al., 1999). By contrast, in the analogous adduct formed by meso-5,7,7,12,14,14-hexa-C-methyl-1,4,8,11-tetraazacyclotetradecane [tet-a, C₁₆H₃₆N₄, (II)] the steric congestion adjacent to the gem-dimethyl units means that only two of the axial N—H bonds are involved in the supramolecular structure, which thus consists of finite aggregates (Gregson et al., 2000). We have now investigated the corresponding adduct formed with 2,2'-biphenol by a third related macrocycle, meso-6,13-diamino-6,13-dimethyl-1,4,8,11-tetraazacyclotetradecane [diammac, C₁₂H₃₀N₆, (III)], based upon the same macrocyclic skeleton as (I) and (II) but bearing pendent hydrogen-bonding functionality. We report here the structural characterization of the resulting 1:2 adduct C₁₂H₃₀N₆·2(C₁₂H₁₀O₂), (IV).

The constitution of the adduct (IV) is that of a salt [C₁₂H₃₂N₆]²⁺·2[HOC₆H₄C₆H₄O]⁻, in which the asymmetric unit consists of one phenolate anion and one half of a [(diammac)H₂]²⁺ cation lying across a centre of inversion (Fig. 1). As commonly found in salts of both [(cyclam)H₂]²⁺ and [(tet-a)H₂]²⁺ cations (Ferguson et al., 1998, 1999; Gregson et al., 2000; Lough et al., 2000), two protons are held by means of N—H···N hydrogen bonds within the N₄ cavity of the macrocycle in an R²₂(10) motif, leaving four axial N—H bonds all of which are essentially normal to the mean plane of the centrosymmetric macrocycle.

The cation in (IV) adopts the trans-III conformation (Barefield et al., 1986; Adam et al., 1994), with almost perfect staggering about the C—C and C—N bonds (Table 1), as typically found in salts of [(cyclam)H₂]²⁺ and [(tet-a)H₂]²⁺ cations. The methyl groups are equatorial and the amino groups, which remain unprotonated, are axial (Fig. 1, Table 1). The configuration of the bonds at the exocyclic N6 is pyramidal, and the conformation about the N6—C6 bond is almost perfectly staggered, with the N lone pair synclinal to C61 (Fig. 1). There are thus four N—H bonds on each face of the macrocycle, all of which participate in formation of intermolecular N—H···O hydrogen bonds (Table 2).

There is a marked difference between the C—N bond lengths involving the protonated N1 and those involving the unprotonated N4 and N6: the values are typical of those observed in [(cyclam)H₂]²⁺ cations where the internal H atoms are fully ordered (Ferguson et al., 1998, 1999). It is notable that the C5—C6 and C6—C7 distances are significantly longer in (IV) than the corresponding distances in the analogous [(cyclam)H₂]²⁺ salt, 1.515 (2) and 1.508 (3) Å: in the [(diammac)H₂]²⁺ cation C6 is a quaternary C atom and both steric and electronic effects may contribute to the bond-length difference. The phenolate anion, in which the two aryl rings are inclined at an angle of 41.0 (1)°, contains a very short intramolecular O—H···O hydrogen bond forming an S(7) motif: as normally observed for bis-phenolate mono-anions, the C—O⁻ bond is significantly shorter than the C—O(H) bond (Table 1).

In the supramolecular structure, each cation acts as an eightfold donor in the formation of N—H···O hydrogen bonds, but none of the N atoms acts as an acceptor of intermolecular hydrogen bonds. The anions, by contrast, act only as acceptors of intermolecular hydrogen bonds and each anion is a fourfold acceptor in the N—H···O hydrogen bonds, consonant with the 1:2 stoichiometry of (IV). Thus, apart from the two types of intramolecular hydrogen bond, all the hydrogen bonds contributing to the supramolecular structure are of N—H···O type.

The supramolecular structure of (IV) is surprisingly similar to that of the corresponding [(cyclam)H₂]²⁺ salt (Ferguson et al., 1999), namely a chain of fused rings. The hydrogen bonds formed by the pendent amino groups serve to reinforce this basic architecture rather than to modify it in any material way: in particular, the amino groups do not lead to the formation of a supramolecular structure having dimensionality greater than one. The supramolecular structure is thus most conveniently described in terms of the amino-induced modification of the fused-ring structure previously reported (Ferguson et al., 1999).

Atoms N1 and N4, both at (x, y, z), act as donors to the anionic O2 atoms in the anions at (x, y, z) and (1 + x, y, z) respectively: at the same time, the symmetry related N1 and N4 in the same cation, which are at (1 − x, 1 − y, 1 − z) act as donors to the O2 atoms in the anions at (1 − x, 1 − y, − z) and (-x, 1 − y, 1 − z) respectively. These hydrogen bonds, together with the intramolecular N—H···N hydrogen bonds within the cations, generate a chain of fused R²₂(10) and R⁴₆(12) rings running parallel to the [100] direction. The R²₂(10) rings are centred at (n + 1/2, 1/2, 1/2) and the R⁴₆(12) rings at (n, 1/2, 1/2) (n = zero or integer). Each cation is thus linked to four different anions, and the two pendent amino groups in each cation form further N—H···O hydrogen bonds to the same four anions. N6 at (x, y, z) acts as donor to the anions at (1 + x, y, z) and (1 − x, 1 − y, 1 − z), via H6B and H6A respectively, while the symmetry-related N6 in the same cation, at (1 − x, 1 − y, 1 − z) similarly acts as donor to the anions at (x, y, z) and (-x, 1 − y, 1 − z). Each cation therefore acts as a double donor of N—H···O hydrogen bonds to each of four anions, and each anion acts as a double acceptor from each of two cations: the anion at (x, y, z) is acceptor from the cations centred at (1/2, 1/2, 1/2) and (−0.5, 1/2, 1/2).

The R⁴₆(12) motif common to both (IV) and its [(cyclam)H₂]²⁺ analogue contains no C atoms: an alternative circuit, about the same centre of inversion but incorporating atoms C5, C6 and C7, has graph-set descriptor R²₄(16). A third motif about the same centre of inversion, of R²₄(14) type, includes the paired N6—H6B···O2 hydrogen bonds (Fig. 2): in both the R²₄(16) and R²₄(14) rings, the sole acceptor is the anionic O2.

S2. Experimental

Equimolar quantities of diammac dihydrate and 2,2'-biphenol were separately dissolved in methanol: the solutions were mixed and the mixture was set aside to crystallize, producing analytically pure (IV). Analysis: found C 68.1, H 8.2, N 13.5%; C₃₆H₅₀N₆O₄ requires C 68.5, H 8.0, N 13.3%. Crystals suitable for single-crystal X-ray diffraction were selected directly from the analytical sample.

S3. Refinement

Compound (IV) crystallized in the triclinic system; space group P-1 was assumed and confirmed by the analysis. H atoms were treated as riding atoms with C—H 0.95 to 0.99, N—H 0.91 and 0.92 Å, O—H 0.84 Å. Examination of the structure with PLATON (Spek, 2000) showed that there were no solvent accessible voids in the crystal lattice.

Computing details

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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP (Johnson, 1976), PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. The molecular components of (IV) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Atoms marked with a star (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
	Fig. 2. Stereoview of part of the crystal structure of (IV), showing the chain of fused rings parallel to [100].

meso-6,13-Diamino-6,13-dimethyl-1,4,8,11- tetraazacyclotetradecane–2,2'-biphenol (1/2)

Crystal data

C12H32N6·2(C12H9O2)	Z = 1
Mr = 630.82	F(000) = 340
Triclinic, P1	Dx = 1.291 Mg m^−3
a = 7.3994 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9179 (4) Å	Cell parameters from 4644 reflections
c = 11.3987 (6) Å	θ = 2.7–30.0°
α = 83.841 (2)°	µ = 0.09 mm^−1
β = 82.063 (2)°	T = 100 K
γ = 79.433 (3)°	Plate, colourless
V = 811.56 (6) Å^3	0.20 × 0.20 × 0.12 mm

Data collection

Kappa-CCD diffractometer	4644 independent reflections
Radiation source: fine-focus sealed X-ray tube	3615 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ϕ scans and ω scans with κ offsets	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→10
Tmin = 0.983, Tmax = 0.990	k = −13→13
15144 measured reflections	l = −15→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0461P)^2 + 0.2179P] where P = (Fo^2 + 2Fc^2)/3
4644 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N1	0.26776 (13)	0.53027 (9)	0.63539 (9)	0.0155 (2)
C2	0.35578 (16)	0.41819 (11)	0.71784 (10)	0.0173 (2)
C3	0.43535 (16)	0.29085 (11)	0.65316 (11)	0.0183 (2)
N4	0.60017 (13)	0.31335 (9)	0.57037 (9)	0.0159 (2)
C5	0.67191 (16)	0.19325 (11)	0.50128 (11)	0.0170 (2)
C6	0.83736 (15)	0.21451 (11)	0.40834 (11)	0.0165 (2)
N6	0.99110 (14)	0.23173 (10)	0.47082 (9)	0.0188 (2)
C61	0.89702 (17)	0.08409 (12)	0.34210 (12)	0.0214 (3)
C7	0.78380 (16)	0.33313 (11)	0.31357 (10)	0.0167 (2)
O1	−0.34095 (11)	0.63896 (8)	0.65499 (8)	0.01968 (19)
C11	−0.25353 (15)	0.61481 (12)	0.85396 (11)	0.0177 (2)
C12	−0.32534 (15)	0.69552 (12)	0.75579 (11)	0.0183 (2)
C13	−0.38331 (16)	0.83775 (12)	0.76135 (12)	0.0213 (3)
C14	−0.36855 (17)	0.90123 (13)	0.86120 (13)	0.0244 (3)
C15	−0.29048 (17)	0.82470 (13)	0.95636 (12)	0.0252 (3)
C16	−0.23330 (17)	0.68370 (13)	0.95163 (12)	0.0222 (3)
O2	−0.07022 (11)	0.45233 (8)	0.65511 (7)	0.01756 (18)
C21	−0.20585 (16)	0.46151 (11)	0.86038 (11)	0.0177 (2)
C22	−0.11255 (15)	0.38814 (11)	0.76320 (11)	0.0164 (2)
C23	−0.06458 (17)	0.24355 (12)	0.78067 (11)	0.0201 (2)
C25	−0.20873 (18)	0.24406 (13)	0.98314 (12)	0.0251 (3)
C24	−0.11128 (18)	0.17297 (12)	0.88916 (12)	0.0236 (3)
C26	−0.25381 (17)	0.38620 (13)	0.96815 (12)	0.0225 (3)
H1A	0.1629	0.5057	0.6150	0.019*
H1B	0.3482	0.5388	0.5669	0.019*
H2A	0.2625	0.3956	0.7845	0.021*
H2B	0.4557	0.4499	0.7513	0.021*
H3A	0.4693	0.2121	0.7116	0.022*
H3B	0.3407	0.2682	0.6085	0.022*
H4A	0.6907	0.3290	0.6125	0.019*
H5A	0.5712	0.1732	0.4605	0.020*
H5B	0.7098	0.1122	0.5566	0.020*
H6A	1.0927	0.2394	0.4172	0.028*
H6B	0.9585	0.3091	0.5105	0.028*
H61A	0.9246	0.0043	0.3994	0.032*
H61B	1.0079	0.0930	0.2859	0.032*
H61C	0.7968	0.0715	0.2986	0.032*
H7A	0.8894	0.3363	0.2503	0.020*
H7B	0.6780	0.3148	0.2769	0.020*
H1	−0.2516	0.5745	0.6422	0.030*
H13	−0.4335	0.8914	0.6955	0.026*
H14	−0.4119	0.9972	0.8645	0.029*
H15	−0.2762	0.8682	1.0240	0.030*
H16	−0.1786	0.6320	1.0167	0.027*
H23	0.0010	0.1936	0.7168	0.024*
H25	−0.2441	0.1958	1.0569	0.030*
H24	−0.0765	0.0757	0.8992	0.028*
H26	−0.3194	0.4344	1.0330	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0150 (4)	0.0163 (4)	0.0145 (5)	−0.0012 (3)	−0.0015 (4)	−0.0014 (3)
C2	0.0175 (5)	0.0184 (5)	0.0143 (6)	−0.0008 (4)	−0.0005 (4)	0.0010 (4)
C3	0.0179 (5)	0.0168 (5)	0.0185 (6)	−0.0027 (4)	0.0008 (4)	0.0010 (4)
N4	0.0149 (4)	0.0169 (4)	0.0158 (5)	−0.0025 (3)	−0.0004 (4)	−0.0035 (4)
C5	0.0183 (5)	0.0150 (5)	0.0177 (6)	−0.0027 (4)	−0.0018 (4)	−0.0017 (4)
C6	0.0159 (5)	0.0161 (5)	0.0171 (6)	−0.0011 (4)	−0.0017 (4)	−0.0028 (4)
N6	0.0164 (5)	0.0202 (5)	0.0194 (5)	−0.0012 (4)	−0.0021 (4)	−0.0033 (4)
C61	0.0219 (6)	0.0181 (5)	0.0238 (7)	−0.0001 (4)	−0.0018 (5)	−0.0063 (5)
C7	0.0173 (5)	0.0171 (5)	0.0155 (6)	−0.0016 (4)	−0.0008 (4)	−0.0042 (4)
O1	0.0185 (4)	0.0213 (4)	0.0196 (4)	−0.0010 (3)	−0.0051 (3)	−0.0043 (3)
C11	0.0129 (5)	0.0218 (5)	0.0183 (6)	−0.0031 (4)	0.0011 (4)	−0.0042 (4)
C12	0.0128 (5)	0.0220 (5)	0.0208 (6)	−0.0040 (4)	−0.0006 (4)	−0.0050 (4)
C13	0.0169 (5)	0.0208 (5)	0.0263 (7)	−0.0024 (4)	−0.0037 (5)	−0.0029 (5)
C14	0.0183 (6)	0.0230 (6)	0.0323 (7)	−0.0035 (4)	0.0005 (5)	−0.0092 (5)
C15	0.0224 (6)	0.0290 (6)	0.0258 (7)	−0.0054 (5)	0.0006 (5)	−0.0122 (5)
C16	0.0195 (6)	0.0282 (6)	0.0192 (6)	−0.0044 (5)	−0.0008 (5)	−0.0056 (5)
O2	0.0187 (4)	0.0186 (4)	0.0152 (4)	−0.0038 (3)	−0.0010 (3)	−0.0012 (3)
C21	0.0149 (5)	0.0213 (5)	0.0178 (6)	−0.0041 (4)	−0.0027 (4)	−0.0024 (4)
C22	0.0144 (5)	0.0191 (5)	0.0171 (6)	−0.0051 (4)	−0.0040 (4)	−0.0011 (4)
C23	0.0206 (6)	0.0199 (5)	0.0207 (6)	−0.0041 (4)	−0.0049 (5)	−0.0025 (4)
C25	0.0267 (6)	0.0278 (6)	0.0217 (7)	−0.0105 (5)	−0.0032 (5)	0.0041 (5)
C24	0.0256 (6)	0.0212 (6)	0.0256 (7)	−0.0079 (5)	−0.0066 (5)	0.0014 (5)
C26	0.0204 (6)	0.0287 (6)	0.0182 (6)	−0.0060 (5)	−0.0002 (5)	−0.0015 (5)

Geometric parameters (Å, º)

N1—C2	1.4908 (14)	O1—C12	1.3590 (14)
N1—H1A	0.92	O1—H1	0.84
N1—H1B	0.92	C11—C16	1.4054 (17)
C2—C3	1.5142 (16)	C11—C12	1.4111 (17)
C2—H2A	0.99	C11—C21	1.4927 (16)
C2—H2B	0.99	C12—C13	1.4028 (16)
C3—N4	1.4713 (14)	C13—C14	1.3846 (18)
C3—H3A	0.99	C13—H13	0.95
C3—H3B	0.99	C14—C15	1.386 (2)
N4—C5	1.4748 (14)	C14—H14	0.9500
N4—H4A	0.92	C15—C16	1.3893 (17)
C5—C6	1.5343 (15)	C15—H15	0.95
C5—H5A	0.99	C16—H16	0.95
C5—H5B	0.99	O2—C22	1.3490 (14)
C6—C7	1.5436 (16)	C21—C26	1.4045 (17)
C7—N1^i	1.4960 (14)	C21—C22	1.4180 (16)
C6—N6	1.4668 (15)	C22—C23	1.4120 (16)
C6—C61	1.5317 (15)	C23—C24	1.3870 (17)
N6—H6A	0.9100	C23—H23	0.95
N6—H6B	0.9100	C25—C26	1.3854 (18)
C61—H61A	0.98	C25—C24	1.3881 (19)
C61—H61B	0.98	C25—H25	0.95
C61—H61C	0.98	C24—H24	0.95
C7—H7A	0.99	C26—H26	0.95
C7—H7B	0.99
C2—N1—C7^i	113.74 (9)	N1^i—C7—H7A	109.1
C2—N1—H1A	108.8	C6—C7—H7A	109.1
C7^i—N1—H1A	108.8	N1^i—C7—H7B	109.1
C2—N1—H1B	108.8	C6—C7—H7B	109.1
C7^i—N1—H1B	108.8	H7A—C7—H7B	107.9
H1A—N1—H1B	107.7	C12—O1—H1	109.5
N1—C2—C3	110.60 (10)	C16—C11—C12	117.45 (11)
N1—C2—H2A	109.5	C16—C11—C21	119.17 (11)
C3—C2—H2A	109.5	C12—C11—C21	123.33 (11)
N1—C2—H2B	109.5	O1—C12—C13	118.55 (11)
C3—C2—H2B	109.5	O1—C12—C11	121.67 (10)
H2A—C2—H2B	108.1	C13—C12—C11	119.79 (11)
N4—C3—C2	110.57 (9)	C14—C13—C12	121.06 (12)
N4—C3—H3A	109.5	C14—C13—H13	119.5
C2—C3—H3A	109.5	C12—C13—H13	119.5
N4—C3—H3B	109.5	C13—C14—C15	119.98 (12)
C2—C3—H3B	109.5	C13—C14—H14	120.0
H3A—C3—H3B	108.1	C15—C14—H14	120.0
C3—N4—C5	111.07 (8)	C14—C15—C16	119.24 (12)
C3—N4—H4A	109.4	C14—C15—H15	120.4
C5—N4—H4A	109.4	C16—C15—H15	120.4
N4—C5—C6	113.24 (9)	C15—C16—C11	122.34 (12)
N4—C5—H5A	108.9	C15—C16—H16	118.8
C6—C5—H5A	108.9	C11—C16—H16	118.8
N4—C5—H5B	108.9	C26—C21—C22	118.34 (10)
C6—C5—H5B	108.9	C26—C21—C11	118.52 (10)
H5A—C5—H5B	107.7	C22—C21—C11	123.14 (10)
N6—C6—C61	108.16 (9)	O2—C22—C23	119.46 (10)
N6—C6—C5	108.31 (10)	O2—C22—C21	121.94 (10)
C61—C6—C5	108.15 (9)	C23—C22—C21	118.60 (11)
N6—C6—C7	114.11 (9)	C24—C23—C22	121.34 (11)
C61—C6—C7	106.25 (10)	C24—C23—H23	119.3
C5—C6—C7	111.64 (9)	C22—C23—H23	119.3
C6—N6—H6A	109.5	C26—C25—C24	119.22 (12)
C6—N6—H6B	109.5	C26—C25—H25	120.4
H6A—N6—H6B	109.5	C24—C25—H25	120.4
C6—C61—H61A	109.5	C23—C24—C25	120.15 (11)
C6—C61—H61B	109.5	C23—C24—H24	119.9
H61A—C61—H61B	109.5	C25—C24—H24	119.9
C6—C61—H61C	109.5	C25—C26—C21	122.28 (12)
H61A—C61—H61C	109.5	C25—C26—H26	118.9
H61B—C61—H61C	109.5	C21—C26—H26	118.9
N1^i—C7—C6	112.33 (9)
C7^i—N1—C2—C3	−169.63 (9)	C14—C15—C16—C11	−0.73 (18)
N1—C2—C3—N4	71.01 (12)	C12—C11—C16—C15	3.59 (17)
C2—C3—N4—C5	−176.37 (9)	C21—C11—C16—C15	−174.08 (11)
C3—N4—C5—C6	176.69 (9)	C12—C11—C21—C22	42.59 (16)
N4—C5—C6—C7	−62.80 (13)	C16—C11—C21—C26	39.40 (15)
C5—C6—C7—N1^i	65.56 (12)	C12—C11—C21—C26	−138.12 (12)
C6—C7—N1^i—C2^i	168.45 (9)	C16—C11—C21—C22	−139.89 (12)
N4—C5—C6—N6	63.65 (12)	C26—C21—C22—O2	176.54 (10)
N4—C5—C6—C61	−179.35 (10)	C11—C21—C22—O2	−4.16 (17)
N6—C6—C7—N1^i	−57.66 (12)	C26—C21—C22—C23	−2.89 (16)
C61—C6—C7—N1^i	−176.75 (9)	C11—C21—C22—C23	176.41 (11)
C16—C11—C12—O1	176.56 (10)	O2—C22—C23—C24	−177.69 (11)
C21—C11—C12—O1	−5.87 (17)	C21—C22—C23—C24	1.75 (17)
C16—C11—C12—C13	−3.70 (16)	C22—C23—C24—C25	0.64 (19)
C21—C11—C12—C13	173.87 (10)	C26—C25—C24—C23	−1.83 (19)
O1—C12—C13—C14	−179.19 (10)	C24—C25—C26—C21	0.62 (19)
C11—C12—C13—C14	1.06 (17)	C22—C21—C26—C25	1.76 (18)
C12—C13—C14—C15	1.91 (18)	C11—C21—C26—C25	−177.56 (11)
C13—C14—C15—C16	−2.08 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	1.65	2.4656 (11)	164
N1—H1A···O2	0.92	1.88	2.7238 (12)	152
N1—H1B···N4^i	0.92	2.07	2.8290 (13)	139
N4—H4A···O2^ii	0.92	2.45	3.3091 (13)	155
N6—H6A···O1^i	0.91	2.39	3.1938 (13)	148
N6—H6B···O2^ii	0.91	2.25	3.1248 (13)	160

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