Hydrogen-bonded sheets in the 1:1 salt of tet-b and trimesic acid

Tet-b (racemic 5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane, C₁₆H₃₆N₄) and trimesic acid (1,3,5-benzene­tri­carboxylic acid, C₉H₆O₆) form a salt partially solvated by both water and methanol, i.e. 5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane-1,3,5-benzene­tri­carboxyl­ic acid-methanol-water (1/1/0.78/1.12), C₁₆H₃₈N₄²⁺·C₉H₄O₆^2-·0.78CH₄O·1.12H₂O. The anions are linked by O-H...O hydrogen bonds [O...O 2.442 (4) and 2.458 (4) Å; O-H...O 170 and 171°] into zigzag chains; orientationally disordered cations are linked to the anion chains by means of N-H...O hydrogen bonds [major orientation: N...O 2.695 (3)-3.071 (4) Å, N-H...O 148-179°; minor orientation: N...O 2.75 (2)-3.34 (2) Å, N-H...O 147-170°] and link the chains into sheets. The solvent mol­ecules are all disordered, but appear to play no significant structural role apart from space filling.

S1. Comment

The meso form of the tetraaza macrocycle 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C₁₆H₃₆N₄ (tet-a), forms a salt with the trigonally trisubstituted benzenecarboxylic acid 3,5-dihydroxybenzoic acid, (I), in which [(HO)₂C₆H₃COO]^- anions form hydrogen-bonded sheets which are linked by the [(tet-a)H₂]²⁺ (C₁₆H₃₈N₄²⁺) dications into a continuous three-dimensional framework based on a pillared-layer architecture (Gregson et al., 2000). With the closely-related acid 5-hydroxyisophthalic acid, (II), both the meso (tet-a) and racemic (tet-b) forms of this tetraaza macrocycle form hydrated salts in which the overall supramolecular structure is two-dimensional, with chains built from anions and water molecules linked together by [(tet-b)H₂]²⁺ dications (Burchell et al., 2000). Continuing this study, we have now investigated the behaviour of the racemic form tet-b with the symmetrically trisubstituted acid 1,3,5-benzenetricarboxylic acid [trimesic acid, C₉H₆O₆, (III)]. The 1:1 adduct, i.e. (1), formed between tet-b and acid (III) proves to be the salt C₁₆H₃₈N₄²⁺·C₉H₄O₆^2-, solvated by both water and methanol. The supramolecular structure consists of two-dimensional hydrogen-bonded sheets in which the solvent molecules play no significant part.

The cation (Fig. 1) is protonated at N14 and N111; the two additional H atoms, captured from the acid, are fully ordered and participate in intramolecular N—H···N hydrogen bonds. The cation in adduct (1) is orientationally disordered, with approximately one eighth of the cation sites containing an orientation in which the cation is rotated by ca 180° about a line through the mid-points of the vectors N11···N14 and N18···N111 (Fig. 2). The conformation of the cation, which is the same for both the major and the minor orientations, is that previously observed for [(tet-b)H₂]²⁺ (Simonov et al., 1998; Burchell et al., 2000), with the four N atoms approaching a tetrahedral arrangement. Although the cation lies in a general position, the magnitudes and signs of the dihedral angles around the ring periphery (Table 1) indicate that the cation has close to C₂ rotational symmetry (Figs. 1 and 2). In contrast, the cation [(tet-a)H₂]²⁺ is generally centrosymmetric (Gregson et al., 2000), so that its four N atoms are strictly coplanar. Within the cation, there are clear difference in the C—N bond lengths involving protonated or unprotonated N atoms, respectively, with those involving protonated N atoms being significantly longer (Table 1). For the longer C—N bonds, there is in addition a clear dependence on the degree of substitution of the C atom involved; the N(H)—CH₂ bonds have a mean length of 1.493 (6) Å, while the N(H)—CMe₂ bonds have a mean length of 1.525 (6) Å.

In the C₉H₄O₆^2- anion (Fig. 1), the remaining carboxylic acid H atom is disordered over two sites, adjacent to O22 and O23, with equal occupancy. The C—O bond lengths (Table 1) are fully consistent with these locations for this H atom. It was found from difference maps that the O22—H222 distance was normal at 0.85 Å, while the O23—H223 distance was longer at 1.10 Å.

The two-dimensional supramolecular structure of adduct (1) is most readily analysed and described using the sub-structure approach (Gregson et al., 2000). The anions form hydrogen-bonded chains, which are linked into sheets by the cations. Each anion is linked to two further anions by means of O—H···O hydrogen bonds: O22 at (x, y, z) acts as donor to O22 at (1 - x, 1 - y, -z), while O23 at (x, y, z) acts as donor to O23 at (2 - x, 1 - y, -z), and these hydrogen bonds generate zigzag chains parallel to the [100] direction (Fig. 3). Averaged over the entire structure, each close inter-anion O···O contact involves two half-H atoms, but at the local level, a given O···O contact can only involve a single H atom; if both H sites were occupied, the H atoms would be within covalent bonding distance. Hence, the carboxyl H_atom locations within each [100] chain must be correlated, but there is no correlation between adjacent chains.

Each cation takes part in four N—H···O hydrogen bonds; the hydrogen-bonding behaviour of the two orientations is similar (Table 2) and only that of the major orientation will be discussed. Both N11 and N18 act as donors, via H11A and H18A, respectively, to O21 within the asymmetric unit, and N14 acts as donor, via H14F, to O24 in the anion at (-1 + x, y, z); this anion is a component of the same [100] chain, running along the line (x, 1/2, 0) as the cation and anion at (x, y, z). N111, however, acts as donor, via H11C, to O26 in the anion at (1 - x, -y, -z), which is a component of the [100] chain along the line (x, -1/2, 0). In this manner, each cation links two adjacent [100] chains, producing a continuous sheet parallel to (001) (Fig. 3). Two such sheets pass through each unit cell, one in the domain -0.27 < z < 0.27, and the other in the domain 0.23 < z < 0.77. There are neither hydrogen bonds nor aromatic π–π stacking interactions between adjacent (001) sheets. The overall structure is thus reminiscent of those found in the salts of both tet-a and tet-b with 5-hydroxyisophthalic acid (Burchell et al., 2000), with anion chains linked into sheets by cation.

Although elemental analysis originally suggested that adduct (1) contained two molecules of methanol per ion-pair, the structure analysis reported here has shown that there are also present in the structure two partial methanol molecules and three partial water molecules. The major methanol component acts as a hydrogen-bond donor, and is pendent from the anion chain (Table 2). For the rest of the solvent molecules no H atoms at all could be located, presumably because of disorder and/or mobility of these components, so that no comment can be made upon any structural role they might have. It is possible that the solvent incorporation are largely adventitious, with the solvent molecules occupying what would otherwise be minor voids in the structure.

The structure reported here is characterized by several forms of disorder: firstly, there is the orientational disorder of the cations; secondly, there is the carboxylic acid H-atom disorder in the anions; and finally, there is the solvent disorder, involving both partial site occupancy and possible orientational disorder. These various forms of disorder allied with the poor crystal quality undoubtedly contribute to the somewhat high R value; nonetheless, the study presented here demonstrates that even apparently intractable systems will yield, given care and persistence.

Related literature

For related literature, see: Burchell et al. (2000); Gregson et al. (2000); Hay et al. (1975); Simonov et al. (1998).

S2. Experimental

A sample of tet-b were prepared, as the monohydrate, according to the literature method of Hay et al. (1975). Equimolar quantities of tet-b and of the acid (III) were separately dissolved in methanol and set aside to crystallize, exposed to the laboratory atmosphere, producing solvated (1). Analysis: found C 57.9, H 9.1, N 10.0%; C₂₇H₅₀N₄O₈ [(1)·2MeOH] requires C 58.0, H 9.0, N 10.0%; C_25.78H_47.36N₄O_7.90 [(1)·0.78MeOH·1.16H₂O] requires C 57.4, H 8.8, N 10.4%. Crystals just adequate for single-crystal X-ray diffraction were selected directly from the analytical sample.

S3. Refinement

Compound (1) is monoclinic and space group P2₁/n was uniquely determined from the systematic absences. The crystal quality was poor and several crystals were used during data collection: two complete data sets were collected at 150 K and that employed here was marginally the better: both sets had rather high merging R factors. It was apparent at an early stage of refinement that the cation was disordered over two sites but that the two orientations had essentially the same conformation; the site-occupation factors (s.o.f.'s) for the major and minor forms of the cations refined to 0.839 (3) and 0.161 (3), respectively. The minor component was refined isotropically, with a common isotropic displacement parameter for the N atoms, a second parameter for all the ring C atoms and a third for the methyl C atoms. In addition to the ionic components, two partial methanol molecules were located: one had an s.o.f. of 0.700 (7) and all its H atoms were located from difference maps; the other had an s.o.f. of 0.084 (4), but its H atoms could not be located. There were also three partial water molecules present: the O atoms for two of them, O61 and O62 were very close together and their s.o.f.'s [0.896 (6) and 0.104 (6)] were constrained to sum to unity, while the s.o.f. of the third, O71, refined to 0.116 (5). Despite extensive searches, no water H atoms could be found, even for O61. The carboxyl H atoms in the anion occupied two sites, with equal occupancy: H222 was located at a normal distance from O22 and was treated as riding with O—H = 0.85 Å, but the other, H223, was clearly more distant from O23 and was treated as riding with O—H = 1.10 Å. All other identified H atoms were treated as riding, with N—H = 0.92 Å and C—H = 0.95 (aromatic), 0.98 (CH₃), 0.99 (CH₂) or 1.00 Å (aliphatic CH).

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. The major ionic components of adduct (1), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The major (N11, N14, N18 and N111) and minor (N31, N34, N38 and N311) orientations of the cation. C and N atoms are depicted as spheres of arbitrary radii, and H atoms have been omitted for clarity.
	Fig. 3. Part of the crystal structure of (1) showing the anion chains parallel to [100] linked into (001) sheets by the cations. Atoms marked with an asterisk (*), hash (#), dollar ($) or at (@) sign are at the symmetry positions (1 - x, 1 - y, -z), (2 - x, 1 - y, -z), (-1 + x, y, z) and (1 - x, -y, -z), respectively.

Racemic 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane– 1,3,5-benzenetricarboxylic acid–methanol–water (1/1/0.78/1.12)

Crystal data

C16H38N4^+·C9H4O6^−·0.78CH4O·1.12H2O	F(000) = 1167
Mr = 539.80	Dx = 1.206 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.8921 (9) Å	Cell parameters from 33988 reflections
b = 15.3390 (6) Å	θ = 2.6–25.0°
c = 14.0209 (8) Å	µ = 0.09 mm^−1
β = 95.666 (2)°	T = 150 K
V = 2973.1 (3) Å^3	Needle, colourless
Z = 4	0.30 × 0.12 × 0.12 mm

Data collection

KappaCCD diffractometer	5228 independent reflections
Radiation source: fine-focus sealed X-ray tube	3154 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ϕ and ω scans with κ offsets	θmax = 25°, θmin = 2.7°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = 0→16
Tmin = 0.974, Tmax = 0.989	k = 0→18
33988 measured reflections	l = −16→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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.212	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0984P)^2 + 2.1918P] where P = (Fo^2 + 2Fc^2)/3
5228 reflections	(Δ/σ)max = 0.004
427 parameters	Δρmax = 0.34 e Å^−3
49 restraints	Δρmin = −0.21 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	Occ. (<1)
N11	0.3034 (4)	0.2973 (3)	−0.0939 (3)	0.0280 (10)	0.839 (3)
N14	0.2053 (6)	0.2931 (4)	0.0854 (4)	0.0283 (10)	0.839 (3)
N18	0.3818 (2)	0.19378 (18)	0.1071 (2)	0.0268 (7)	0.839 (3)
N111	0.3386 (2)	0.11235 (17)	−0.0844 (2)	0.0242 (7)	0.839 (3)
C12	0.2333 (3)	0.3627 (3)	−0.0681 (3)	0.0317 (11)	0.839 (3)
C13	0.2387 (3)	0.3740 (3)	0.0385 (3)	0.0320 (11)	0.839 (3)
C15	0.2153 (4)	0.2909 (3)	0.1950 (4)	0.0389 (13)	0.839 (3)
C16	0.3222 (3)	0.2829 (3)	0.2336 (3)	0.0422 (11)	0.839 (3)
C17	0.3786 (3)	0.2004 (3)	0.2111 (3)	0.0390 (10)	0.839 (3)
C19	0.4285 (3)	0.1143 (2)	0.0748 (3)	0.0289 (9)	0.839 (3)
C110	0.4362 (3)	0.1173 (2)	−0.0308 (3)	0.0263 (9)	0.839 (3)
C112	0.3305 (3)	0.1226 (2)	−0.1927 (3)	0.0287 (9)	0.839 (3)
C113	0.3700 (4)	0.2118 (4)	−0.2206 (5)	0.0357 (13)	0.839 (3)
C114	0.3150 (3)	0.2927 (3)	−0.1961 (3)	0.0368 (12)	0.839 (3)
C115	0.1728 (5)	0.3751 (4)	0.2318 (5)	0.0619 (19)	0.839 (3)
C116	0.1570 (4)	0.2122 (4)	0.2226 (5)	0.0600 (18)	0.839 (3)
C117	0.4798 (4)	0.2040 (4)	0.2679 (4)	0.0704 (16)	0.839 (3)
C118	0.3877 (3)	0.0496 (2)	−0.2352 (3)	0.0414 (11)	0.839 (3)
C119	0.2229 (3)	0.1125 (3)	−0.2251 (3)	0.0442 (11)	0.839 (3)
C120	0.3662 (4)	0.3733 (3)	−0.2319 (4)	0.0525 (15)	0.839 (3)
O21	0.49535 (17)	0.33758 (14)	0.0148 (2)	0.0551 (8)
O22	0.57725 (17)	0.46070 (14)	0.0017 (2)	0.0552 (8)
O23	0.92390 (16)	0.45964 (13)	−0.0060 (2)	0.0501 (7)
O24	1.00990 (17)	0.33809 (14)	0.0230 (2)	0.0525 (8)
O25	0.82406 (19)	0.05433 (15)	−0.0089 (2)	0.0628 (9)
O26	0.67795 (18)	0.05799 (14)	0.0419 (2)	0.0524 (8)
C21	0.6654 (2)	0.32963 (18)	0.0083 (2)	0.0262 (8)
C22	0.7517 (2)	0.37366 (18)	0.0030 (2)	0.0272 (7)
C23	0.8387 (2)	0.32868 (18)	0.0054 (2)	0.0269 (7)
C24	0.8383 (2)	0.23831 (18)	0.0081 (2)	0.0299 (8)
C25	0.7523 (2)	0.19262 (19)	0.0124 (2)	0.0292 (8)
C26	0.6675 (2)	0.2395 (2)	0.0145 (2)	0.0325 (8)
C27	0.5710 (2)	0.3779 (2)	0.0080 (3)	0.0362 (9)
C28	0.9329 (2)	0.3775 (2)	0.0071 (3)	0.0341 (8)
C29	0.7514 (3)	0.0940 (2)	0.0155 (3)	0.0386 (9)
N31	0.1186 (14)	0.1906 (12)	−0.1054 (11)	0.057 (4)*	0.161 (3)
N34	0.1624 (13)	0.1102 (13)	0.0848 (12)	0.057 (4)*	0.161 (3)
N38	0.201 (4)	0.299 (3)	0.099 (3)	0.057 (4)*	0.161 (3)
N311	0.292 (3)	0.291 (2)	−0.0828 (19)	0.057 (4)*	0.161 (3)
C32	0.0686 (19)	0.1133 (15)	−0.0731 (15)	0.055 (3)*	0.161 (3)
C33	0.0633 (15)	0.1176 (16)	0.0332 (14)	0.055 (3)*	0.161 (3)
C35	0.1713 (14)	0.1214 (12)	0.1944 (13)	0.055 (3)*	0.161 (3)
C36	0.125 (2)	0.2099 (14)	0.215 (3)	0.055 (3)*	0.161 (3)
C37	0.189 (3)	0.2900 (17)	0.201 (3)	0.055 (3)*	0.161 (3)
C39	0.266 (2)	0.366 (2)	0.0683 (18)	0.055 (3)*	0.161 (3)
C310	0.259 (3)	0.374 (2)	−0.0388 (18)	0.055 (3)*	0.161 (3)
C312	0.2852 (17)	0.287 (2)	−0.192 (2)	0.055 (3)*	0.161 (3)
C313	0.1799 (14)	0.2765 (13)	−0.2321 (16)	0.055 (3)*	0.161 (3)
C314	0.1246 (14)	0.1962 (14)	−0.2094 (13)	0.055 (3)*	0.161 (3)
C315	0.1145 (18)	0.0456 (14)	0.2365 (18)	0.068 (4)*	0.161 (3)
C316	0.2816 (14)	0.1089 (17)	0.2261 (18)	0.068 (4)*	0.161 (3)
C317	0.147 (3)	0.369 (2)	0.249 (3)	0.068 (4)*	0.161 (3)
C318	0.327 (2)	0.371 (2)	−0.230 (3)	0.068 (4)*	0.161 (3)
C319	0.349 (3)	0.210 (3)	−0.216 (4)	0.068 (4)*	0.161 (3)
C320	0.0245 (15)	0.2054 (18)	−0.2677 (17)	0.068 (4)*	0.161 (3)
O41	0.9674 (2)	0.0962 (2)	−0.1109 (3)	0.0442 (12)	0.700 (7)
C42	0.9740 (4)	0.0247 (3)	−0.1733 (4)	0.0564 (18)	0.700 (7)
O51	0.530 (2)	0.0951 (15)	0.1172 (18)	0.040*	0.084 (4)
C52	0.527 (3)	0.021 (2)	0.179 (3)	0.040*	0.084 (4)
O61	0.8520 (2)	−0.12430 (16)	0.0022 (2)	0.0486 (10)	0.896 (6)
O62	0.927 (2)	−0.1209 (16)	0.028 (2)	0.048*	0.104 (6)
O71	0.6442 (15)	−0.1252 (12)	−0.0073 (15)	0.040*	0.116 (5)
H11A	0.3625	0.3096	−0.0611	0.034*	0.839 (3)
H14E	0.2392	0.2466	0.0642	0.034*	0.839 (3)
H14F	0.1412	0.2846	0.0643	0.034*	0.839 (3)
H18A	0.4143	0.2415	0.0867	0.032*	0.839 (3)
H11C	0.3007	0.1547	−0.0604	0.029*	0.839 (3)
H11D	0.3121	0.0593	−0.0710	0.029*	0.839 (3)
H2A	0.1672	0.3442	−0.0927	0.038*	0.839 (3)
H2B	0.2468	0.4191	−0.0983	0.038*	0.839 (3)
H3A	0.3062	0.3871	0.0639	0.038*	0.839 (3)
H3B	0.1977	0.4238	0.0540	0.038*	0.839 (3)
H6A	0.3260	0.2887	0.3042	0.051*	0.839 (3)
H6B	0.3567	0.3334	0.2093	0.051*	0.839 (3)
H7	0.3433	0.1485	0.2332	0.047*	0.839 (3)
H9A	0.3902	0.0626	0.0903	0.035*	0.839 (3)
H9B	0.4939	0.1086	0.1093	0.035*	0.839 (3)
H10A	0.4683	0.1721	−0.0473	0.032*	0.839 (3)
H10B	0.4762	0.0679	−0.0495	0.032*	0.839 (3)
H13A	0.4370	0.2172	−0.1897	0.043*	0.839 (3)
H13B	0.3739	0.2117	−0.2907	0.043*	0.839 (3)
H14	0.2490	0.2897	−0.2316	0.044*	0.839 (3)
H51A	0.1066	0.3827	0.2020	0.093*	0.839 (3)
H51B	0.2125	0.4247	0.2155	0.093*	0.839 (3)
H51C	0.1723	0.3717	0.3016	0.093*	0.839 (3)
H52A	0.1580	0.2094	0.2925	0.090*	0.839 (3)
H52B	0.1856	0.1588	0.1992	0.090*	0.839 (3)
H52C	0.0901	0.2177	0.1939	0.090*	0.839 (3)
H71A	0.5148	0.1499	0.2575	0.106*	0.839 (3)
H71B	0.4726	0.2106	0.3364	0.106*	0.839 (3)
H71C	0.5159	0.2537	0.2459	0.106*	0.839 (3)
H12D	0.3713	0.0474	−0.3047	0.062*	0.839 (3)
H12E	0.3714	−0.0062	−0.2069	0.062*	0.839 (3)
H12F	0.4571	0.0607	−0.2212	0.062*	0.839 (3)
H12A	0.1856	0.1522	−0.1882	0.066*	0.839 (3)
H12B	0.2030	0.0523	−0.2144	0.066*	0.839 (3)
H12C	0.2111	0.1264	−0.2935	0.066*	0.839 (3)
H14A	0.3283	0.4256	−0.2209	0.079*	0.839 (3)
H14B	0.3724	0.3672	−0.3006	0.079*	0.839 (3)
H14C	0.4307	0.3785	−0.1971	0.079*	0.839 (3)
H222	0.5216	0.4832	0.0038	0.083*	0.50
H223	0.9957	0.4905	0.0032	0.075*	0.50
H22	0.7515	0.4354	−0.0024	0.033*
H24	0.8974	0.2073	0.0071	0.036*
H26	0.6090	0.2089	0.0205	0.039*
H31A	0.0873	0.2395	−0.0863	0.069*	0.161 (3)
H34A	0.2011	0.1513	0.0599	0.069*	0.161 (3)
H34B	0.1868	0.0563	0.0714	0.069*	0.161 (3)
H38A	0.1405	0.3086	0.0673	0.069*	0.161 (3)
H31C	0.2553	0.2456	−0.0621	0.069*	0.161 (3)
H31D	0.3548	0.2810	−0.0594	0.069*	0.161 (3)
H32A	0.1039	0.0601	−0.0892	0.066*	0.161 (3)
H32B	0.0025	0.1104	−0.1064	0.066*	0.161 (3)
H33A	0.0336	0.1735	0.0500	0.066*	0.161 (3)
H33B	0.0222	0.0696	0.0532	0.066*	0.161 (3)
H36A	0.0645	0.2160	0.1725	0.066*	0.161 (3)
H36B	0.1083	0.2096	0.2819	0.066*	0.161 (3)
H37	0.2545	0.2783	0.2354	0.066*	0.161 (3)
H39A	0.3333	0.3516	0.0927	0.066*	0.161 (3)
H39B	0.2495	0.4228	0.0962	0.066*	0.161 (3)
H31E	0.2993	0.4229	−0.0571	0.066*	0.161 (3)
H31F	0.1908	0.3861	−0.0637	0.066*	0.161 (3)
H31G	0.1439	0.3274	−0.2106	0.066*	0.161 (3)
H31H	0.1778	0.2805	−0.3027	0.066*	0.161 (3)
H314	0.1583	0.1434	−0.2315	0.066*	0.161 (3)
H31I	0.1489	−0.0094	0.2291	0.102*	0.161 (3)
H31J	0.0496	0.0419	0.2023	0.102*	0.161 (3)
H31K	0.1092	0.0564	0.3047	0.102*	0.161 (3)
H31L	0.3021	0.0513	0.2057	0.102*	0.161 (3)
H31M	0.2930	0.1135	0.2960	0.102*	0.161 (3)
H31N	0.3186	0.1540	0.1964	0.102*	0.161 (3)
H31O	0.1907	0.4189	0.2465	0.102*	0.161 (3)
H31P	0.1385	0.3554	0.3159	0.102*	0.161 (3)
H31Q	0.0838	0.3839	0.2149	0.102*	0.161 (3)
H31R	0.3952	0.3768	−0.2057	0.102*	0.161 (3)
H31S	0.2909	0.4217	−0.2095	0.102*	0.161 (3)
H31T	0.3215	0.3695	−0.3006	0.102*	0.161 (3)
H31U	0.4155	0.2207	−0.1892	0.102*	0.161 (3)
H31V	0.3462	0.2036	−0.2854	0.102*	0.161 (3)
H31W	0.3247	0.1568	−0.1877	0.102*	0.161 (3)
H32C	−0.0165	0.1559	−0.2539	0.102*	0.161 (3)
H32D	0.0327	0.2065	−0.3363	0.102*	0.161 (3)
H32E	−0.0062	0.2597	−0.2498	0.102*	0.161 (3)
H41	0.9243	0.0864	−0.0743	0.066*	0.700 (7)
H42A	1.0196	0.0386	−0.2202	0.085*	0.700 (7)
H42B	0.9102	0.0126	−0.2069	0.085*	0.700 (7)
H42C	0.9969	−0.0266	−0.1362	0.085*	0.700 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.030 (2)	0.0212 (18)	0.033 (2)	−0.0011 (15)	0.0034 (16)	0.0037 (14)
N14	0.024 (2)	0.0273 (19)	0.034 (3)	−0.0017 (15)	0.0027 (18)	−0.0034 (16)
N18	0.0270 (18)	0.0260 (16)	0.0273 (19)	0.0010 (13)	0.0020 (13)	0.0004 (12)
N111	0.0191 (17)	0.0146 (15)	0.039 (2)	−0.0030 (12)	0.0010 (14)	−0.0006 (12)
C12	0.031 (3)	0.024 (2)	0.040 (3)	0.0032 (18)	0.004 (2)	0.0049 (18)
C13	0.027 (3)	0.022 (2)	0.047 (3)	0.0003 (17)	0.003 (2)	−0.0021 (19)
C15	0.041 (4)	0.050 (3)	0.027 (3)	0.006 (2)	0.008 (2)	−0.0010 (18)
C16	0.046 (3)	0.051 (3)	0.028 (2)	0.009 (2)	−0.001 (2)	−0.0065 (19)
C17	0.041 (3)	0.046 (2)	0.030 (2)	0.009 (2)	0.0012 (19)	0.0043 (18)
C19	0.026 (2)	0.0195 (19)	0.040 (2)	0.0016 (15)	−0.0049 (17)	0.0020 (16)
C110	0.019 (2)	0.022 (2)	0.037 (2)	0.0001 (15)	0.0028 (17)	0.0010 (15)
C112	0.037 (2)	0.023 (2)	0.026 (2)	−0.0024 (16)	0.0031 (17)	−0.0039 (15)
C113	0.047 (3)	0.030 (2)	0.032 (2)	0.002 (2)	0.013 (2)	0.0054 (17)
C114	0.049 (3)	0.026 (2)	0.036 (3)	0.000 (2)	0.005 (2)	0.0075 (17)
C115	0.063 (5)	0.083 (4)	0.040 (4)	0.025 (3)	0.014 (3)	−0.013 (3)
C116	0.059 (4)	0.078 (4)	0.045 (3)	−0.011 (3)	0.013 (3)	0.010 (2)
C117	0.066 (4)	0.090 (4)	0.051 (3)	0.031 (3)	−0.012 (3)	−0.015 (3)
C118	0.053 (3)	0.034 (2)	0.039 (3)	0.000 (2)	0.013 (2)	−0.0022 (18)
C119	0.050 (3)	0.041 (2)	0.039 (3)	−0.001 (2)	−0.004 (2)	−0.0048 (19)
C120	0.078 (4)	0.035 (2)	0.047 (3)	−0.001 (3)	0.021 (3)	0.012 (2)
O21	0.0226 (14)	0.0342 (14)	0.109 (2)	−0.0042 (11)	0.0118 (14)	0.0078 (13)
O22	0.0205 (14)	0.0245 (14)	0.122 (2)	0.0015 (10)	0.0122 (15)	0.0074 (13)
O23	0.0211 (14)	0.0218 (13)	0.108 (2)	−0.0025 (10)	0.0074 (14)	0.0085 (12)
O24	0.0238 (14)	0.0293 (14)	0.105 (2)	0.0010 (11)	0.0095 (13)	0.0021 (13)
O25	0.0437 (18)	0.0247 (14)	0.124 (3)	0.0006 (12)	0.0283 (17)	−0.0064 (14)
O26	0.0401 (16)	0.0224 (13)	0.096 (2)	−0.0072 (11)	0.0133 (14)	0.0088 (12)
C21	0.0222 (18)	0.0182 (16)	0.038 (2)	−0.0008 (12)	0.0018 (14)	0.0003 (12)
C22	0.0265 (17)	0.0186 (15)	0.0371 (19)	−0.0011 (14)	0.0055 (14)	0.0021 (13)
C23	0.0222 (18)	0.0215 (17)	0.038 (2)	−0.0029 (13)	0.0067 (14)	0.0008 (13)
C24	0.0231 (19)	0.0227 (17)	0.045 (2)	0.0011 (13)	0.0087 (15)	−0.0016 (14)
C25	0.0288 (19)	0.0207 (16)	0.038 (2)	−0.0042 (14)	0.0056 (15)	−0.0007 (13)
C26	0.0225 (19)	0.0304 (19)	0.046 (2)	−0.0059 (14)	0.0086 (15)	0.0000 (14)
C27	0.0209 (19)	0.0271 (19)	0.061 (2)	−0.0036 (14)	0.0058 (16)	0.0040 (15)
C28	0.0221 (19)	0.0253 (19)	0.056 (2)	−0.0002 (14)	0.0112 (16)	−0.0045 (15)
C29	0.030 (2)	0.0262 (18)	0.060 (3)	−0.0035 (16)	0.0075 (18)	0.0018 (16)
O41	0.032 (2)	0.037 (2)	0.064 (3)	−0.0001 (15)	0.0119 (17)	−0.0069 (17)
C42	0.049 (4)	0.048 (3)	0.075 (4)	0.004 (3)	0.019 (3)	−0.012 (3)
O61	0.044 (2)	0.0392 (16)	0.064 (2)	−0.0071 (13)	0.0124 (16)	−0.0055 (13)

Geometric parameters (Å, º)

N11—C12	1.467 (5)	C23—C28	1.506 (4)
N11—C114	1.460 (5)	C24—C25	1.391 (4)
N11—H11A	0.92	C24—H24	0.95
N14—C13	1.499 (6)	C25—C26	1.383 (4)
N14—C15	1.530 (6)	C25—C29	1.513 (4)
N14—H14E	0.92	C26—H26	0.95
N14—H14F	0.92	N31—C32	1.468 (17)
N18—C17	1.467 (5)	N31—C314	1.471 (17)
N18—C19	1.473 (4)	N31—H31A	0.92
N18—H18A	0.92	N34—C33	1.495 (17)
N111—C110	1.487 (4)	N34—C35	1.539 (17)
N111—C112	1.520 (5)	N34—H34A	0.92
N111—H11C	0.92	N34—H34B	0.92
N111—H11D	0.92	N38—C37	1.47 (2)
C12—C13	1.499 (6)	N38—C39	1.47 (2)
C12—H2A	0.99	N38—H38A	0.92
C12—H2B	0.99	N311—C310	1.50 (2)
C13—H3A	0.99	N311—C312	1.524 (19)
C13—H3B	0.99	N311—H31C	0.92
C15—C16	1.534 (7)	N311—H31D	0.92
C15—C115	1.530 (6)	C32—C33	1.500 (18)
C15—C116	1.525 (6)	C32—H32A	0.99
C16—C17	1.537 (5)	C32—H32B	0.99
C16—H6A	0.99	C33—H33A	0.99
C16—H6B	0.99	C33—H33B	0.99
C17—C117	1.547 (6)	C35—C36	1.539 (18)
C17—H7	1.00	C35—C315	1.555 (17)
C19—C110	1.496 (5)	C35—C316	1.564 (17)
C19—H9A	0.99	C36—C37	1.538 (19)
C19—H9B	0.99	C36—H36A	0.99
C110—H10A	0.99	C36—H36B	0.99
C110—H10B	0.99	C37—C317	1.53 (2)
C112—C113	1.539 (7)	C37—H37	1.00
C112—C118	1.528 (5)	C39—C310	1.501 (19)
C112—C119	1.526 (5)	C39—H39A	0.99
C113—C114	1.515 (6)	C39—H39B	0.99
C113—H13A	0.99	C310—H31E	0.99
C113—H13B	0.99	C310—H31F	0.99
C114—C120	1.535 (6)	C312—C313	1.524 (19)
C114—H14	1.00	C312—C318	1.533 (19)
C115—H51A	0.98	C312—C319	1.534 (19)
C115—H51B	0.98	C313—C314	1.503 (17)
C115—H51C	0.98	C313—H31G	0.99
C116—H52A	0.98	C313—H31H	0.99
C116—H52B	0.98	C314—C320	1.549 (18)
C116—H52C	0.98	C314—H314	1.00
C117—H71A	0.98	C315—H31I	0.98
C117—H71B	0.98	C315—H31J	0.98
C117—H71C	0.98	C315—H31K	0.98
C118—H12D	0.98	C316—H31L	0.98
C118—H12E	0.98	C316—H31M	0.98
C118—H12F	0.98	C316—H31N	0.98
C119—H12A	0.98	C317—H31O	0.98
C119—H12B	0.98	C317—H31P	0.98
C119—H12C	0.98	C317—H31Q	0.98
C120—H14A	0.98	C318—H31R	0.98
C120—H14B	0.98	C318—H31S	0.98
C120—H14C	0.98	C318—H31T	0.98
O21—C27	1.231 (4)	C319—H31U	0.98
O22—C27	1.276 (4)	C319—H31V	0.98
O22—H222	0.85	C319—H31W	0.98
O23—C28	1.278 (4)	C320—H32C	0.98
O23—H223	1.10	C320—H32D	0.98
O24—C28	1.230 (4)	C320—H32E	0.98
O25—C29	1.255 (4)	O41—C42	1.411 (6)
O26—C29	1.248 (4)	O41—H41	0.84
C21—C22	1.385 (4)	C42—H42A	0.98
C21—C26	1.386 (4)	C42—H42B	0.98
C21—C27	1.506 (4)	C42—H42C	0.98
C22—C23	1.388 (4)	O51—C52	1.439 (10)
C22—H22	0.95	O61—O62	1.08 (3)
C23—C24	1.387 (4)
C114—N11—C12	114.5 (4)	C26—C25—C29	120.6 (3)
C114—N11—H11A	108.6	C24—C25—C29	121.0 (3)
C12—N11—H11A	108.6	C25—C26—C21	122.0 (3)
C13—N14—C15	117.2 (4)	C25—C26—H26	119.0
C13—N14—H14E	108.0	C21—C26—H26	119.0
C15—N14—H14E	108.0	O21—C27—O22	124.8 (3)
C13—N14—H14F	108.0	O21—C27—C21	120.1 (3)
C15—N14—H14F	108.0	O22—C27—C21	115.1 (3)
H14E—N14—H14F	107.2	O24—C28—O23	125.5 (3)
C17—N18—C19	114.9 (3)	O24—C28—C23	119.9 (3)
C17—N18—H18A	108.6	O23—C28—C23	114.6 (3)
C19—N18—H18A	108.6	O26—C29—O25	124.7 (3)
C110—N111—C112	118.3 (3)	O26—C29—C25	117.4 (3)
C110—N111—H11C	107.7	O25—C29—C25	117.8 (3)
C112—N111—H11C	107.7	C32—N31—C314	115.3 (15)
C110—N111—H11D	107.7	C32—N31—H31A	108.4
C112—N111—H11D	107.7	C314—N31—H31A	108.4
H11C—N111—H11D	107.1	C33—N34—C35	117.0 (15)
N11—C12—C13	110.8 (3)	C33—N34—H34A	108.0
N11—C12—H2A	109.5	C35—N34—H34A	108.0
C13—C12—H2A	109.5	C33—N34—H34B	108.0
N11—C12—H2B	109.5	C35—N34—H34B	108.0
C13—C12—H2B	109.5	H34A—N34—H34B	107.3
H2A—C12—H2B	108.1	C37—N38—C39	119 (3)
N14—C13—C12	110.8 (3)	C37—N38—H38A	107.6
N14—C13—H3A	109.5	C39—N38—H38A	107.6
C12—C13—H3A	109.5	C310—N311—C312	117 (2)
N14—C13—H3B	109.5	C310—N311—H31C	108.1
C12—C13—H3B	109.5	C312—N311—H31C	108.1
H3A—C13—H3B	108.1	C310—N311—H31D	108.1
C116—C15—N14	105.9 (4)	C312—N311—H31D	108.1
C116—C15—C115	110.5 (4)	H31C—N311—H31D	107.3
N14—C15—C115	108.7 (4)	N31—C32—C33	110.0 (17)
C116—C15—C16	111.5 (4)	N31—C32—H32A	109.7
N14—C15—C16	110.2 (4)	C33—C32—H32A	109.7
C115—C15—C16	109.9 (5)	N31—C32—H32B	109.7
C15—C16—C17	119.3 (4)	C33—C32—H32B	109.7
C15—C16—H6A	107.5	H32A—C32—H32B	108.2
C17—C16—H6A	107.5	N34—C33—C32	110.1 (17)
C15—C16—H6B	107.5	N34—C33—H33A	109.6
C17—C16—H6B	107.5	C32—C33—H33A	109.6
H6A—C16—H6B	107.0	N34—C33—H33B	109.6
N18—C17—C16	109.1 (3)	C32—C33—H33B	109.6
N18—C17—C117	113.5 (4)	H33A—C33—H33B	108.1
C16—C17—C117	108.7 (3)	N34—C35—C36	107.0 (17)
N18—C17—H7	108.5	N34—C35—C315	107.5 (15)
C16—C17—H7	108.5	C36—C35—C315	110.7 (16)
C117—C17—H7	108.5	N34—C35—C316	104.5 (15)
N18—C19—C110	110.8 (3)	C36—C35—C316	117.9 (17)
N18—C19—H9A	109.5	C315—C35—C316	108.6 (16)
C110—C19—H9A	109.5	C37—C36—C35	115.2 (19)
N18—C19—H9B	109.5	C37—C36—H36A	108.5
C110—C19—H9B	109.5	C35—C36—H36A	108.5
H9A—C19—H9B	108.1	C37—C36—H36B	108.5
N111—C110—C19	110.4 (3)	C35—C36—H36B	108.5
N111—C110—H10A	109.6	H36A—C36—H36B	107.5
C19—C110—H10A	109.6	N38—C37—C317	116 (3)
N111—C110—H10B	109.6	N38—C37—C36	108 (2)
C19—C110—H10B	109.6	C317—C37—C36	109 (2)
H10A—C110—H10B	108.1	N38—C37—H37	107.7
N111—C112—C119	105.1 (3)	C317—C37—H37	107.7
N111—C112—C118	108.8 (3)	C36—C37—H37	107.7
C119—C112—C118	109.9 (3)	N38—C39—C310	111 (2)
N111—C112—C113	110.7 (3)	N38—C39—H39A	109.3
C119—C112—C113	112.3 (3)	C310—C39—H39A	109.3
C118—C112—C113	109.9 (3)	N38—C39—H39B	109.3
C114—C113—C112	118.0 (4)	C310—C39—H39B	109.3
C114—C113—H13A	107.8	H39A—C39—H39B	108.0
C112—C113—H13A	107.8	C39—C310—N311	111 (2)
C114—C113—H13B	107.8	C39—C310—H31E	109.5
C112—C113—H13B	107.8	N311—C310—H31E	109.5
H13A—C113—H13B	107.1	C39—C310—H31F	109.5
N11—C114—C113	111.7 (4)	N311—C310—H31F	109.5
N11—C114—C120	112.5 (4)	H31E—C310—H31F	108.1
C113—C114—C120	108.9 (4)	N311—C312—C313	110 (2)
N11—C114—H14	107.9	N311—C312—C318	110 (2)
C113—C114—H14	107.9	C313—C312—C318	110 (2)
C120—C114—H14	107.9	N311—C312—C319	106 (2)
C15—C115—H51A	109.5	C313—C312—C319	113 (2)
C15—C115—H51B	109.5	C318—C312—C319	109 (2)
H51A—C115—H51B	109.5	C314—C313—C312	120.2 (17)
C15—C115—H51C	109.5	C314—C313—H31G	107.3
H51A—C115—H51C	109.5	C312—C313—H31G	107.3
H51B—C115—H51C	109.5	C314—C313—H31H	107.3
C15—C116—H52A	109.5	C312—C313—H31H	107.3
C15—C116—H52B	109.5	H31G—C313—H31H	106.9
H52A—C116—H52B	109.5	N31—C314—C313	109.7 (15)
C15—C116—H52C	109.5	N31—C314—C320	113.1 (17)
H52A—C116—H52C	109.5	C313—C314—C320	105.3 (16)
H52B—C116—H52C	109.5	N31—C314—H314	109.5
C17—C117—H71A	109.5	C313—C314—H314	109.5
C17—C117—H71B	109.5	C320—C314—H314	109.5
H71A—C117—H71B	109.5	C35—C315—H31I	109.5
C17—C117—H71C	109.5	C35—C315—H31J	109.5
H71A—C117—H71C	109.5	H31I—C315—H31J	109.5
H71B—C117—H71C	109.5	C35—C315—H31K	109.5
C112—C118—H12D	109.5	H31I—C315—H31K	109.5
C112—C118—H12E	109.5	H31J—C315—H31K	109.5
H12D—C118—H12E	109.5	C35—C316—H31L	109.5
C112—C118—H12F	109.5	C35—C316—H31M	109.5
H12D—C118—H12F	109.5	H31L—C316—H31M	109.5
H12E—C118—H12F	109.5	C35—C316—H31N	109.5
C112—C119—H12A	109.5	H31L—C316—H31N	109.5
C112—C119—H12B	109.5	H31M—C316—H31N	109.5
H12A—C119—H12B	109.5	C37—C317—H31O	109.5
C112—C119—H12C	109.5	C37—C317—H31P	109.5
H12A—C119—H12C	109.5	H31O—C317—H31P	109.5
H12B—C119—H12C	109.5	C37—C317—H31Q	109.5
C114—C120—H14A	109.5	H31O—C317—H31Q	109.5
C114—C120—H14B	109.5	H31P—C317—H31Q	109.5
H14A—C120—H14B	109.5	C312—C318—H31R	109.5
C114—C120—H14C	109.5	C312—C318—H31S	109.5
H14A—C120—H14C	109.5	H31R—C318—H31S	109.5
H14B—C120—H14C	109.5	C312—C318—H31T	109.5
C27—O22—H222	109.5	H31R—C318—H31T	109.5
C28—O23—H223	109.5	H31S—C318—H31T	109.5
C22—C21—C26	118.5 (3)	C312—C319—H31U	109.5
C22—C21—C27	121.2 (3)	C312—C319—H31V	109.5
C26—C21—C27	120.3 (3)	H31U—C319—H31V	109.5
C21—C22—C23	120.8 (3)	C312—C319—H31W	109.5
C21—C22—H22	119.6	H31U—C319—H31W	109.5
C23—C22—H22	119.6	H31V—C319—H31W	109.5
C24—C23—C22	119.5 (3)	C314—C320—H32C	109.5
C24—C23—C28	120.1 (3)	C314—C320—H32D	109.5
C22—C23—C28	120.4 (3)	H32C—C320—H32D	109.5
C23—C24—C25	120.7 (3)	C314—C320—H32E	109.5
C23—C24—H24	119.7	H32C—C320—H32E	109.5
C25—C24—H24	119.7	H32D—C320—H32E	109.5
C26—C25—C24	118.4 (3)
N11—C12—C13—N14	−67.0 (5)	C22—C21—C27—O21	−178.5 (3)
C12—C13—N14—C15	174.4 (5)	C26—C21—C27—O21	1.0 (5)
C13—N14—C15—C116	168.0 (6)	C22—C21—C27—O22	0.7 (5)
C13—N14—C15—C115	49.2 (7)	C26—C21—C27—O22	−179.8 (3)
C13—N14—C15—C16	−71.3 (7)	C24—C23—C28—O24	−9.1 (5)
C116—C15—C16—C17	53.3 (5)	C22—C23—C28—O23	−8.4 (5)
N14—C15—C16—C17	−64.0 (5)	C22—C23—C28—O24	169.6 (3)
C115—C15—C16—C17	176.2 (4)	C24—C23—C28—O23	172.9 (3)
C19—N18—C17—C117	62.4 (4)	C26—C25—C29—O26	−16.2 (5)
C15—C16—C17—N18	62.5 (5)	C24—C25—C29—O25	−16.9 (5)
C16—C17—N18—C19	−176.2 (3)	C24—C25—C29—O26	163.3 (3)
C15—C16—C17—C117	−173.3 (4)	C26—C25—C29—O25	163.6 (3)
C17—N18—C19—C110	−174.9 (3)	C314—N31—C32—C33	−177.3 (18)
N18—C19—C110—N111	−67.6 (4)	C35—N34—C33—C32	174.8 (16)
C19—C110—N111—C112	174.6 (3)	N31—C32—C33—N34	−67 (3)
C110—N111—C112—C119	178.8 (3)	C33—N34—C35—C36	−55 (2)
C110—N111—C112—C118	61.1 (4)	C33—N34—C35—C315	64 (2)
C110—N111—C112—C113	−59.8 (4)	C33—N34—C35—C316	179.2 (18)
N111—C112—C113—C114	−67.3 (6)	N34—C35—C36—C37	−79 (3)
C119—C112—C113—C114	49.7 (6)	C315—C35—C36—C37	164 (3)
C118—C112—C113—C114	172.4 (5)	C316—C35—C36—C37	39 (3)
C12—N11—C114—C120	70.0 (6)	C39—N38—C37—C317	62 (6)
C112—C113—C114—N11	56.2 (6)	C39—N38—C37—C36	−175 (4)
C113—C114—N11—C12	−167.2 (4)	C35—C36—C37—N38	68 (4)
C114—N11—C12—C13	−170.0 (4)	C35—C36—C37—C317	−165 (3)
C112—C113—C114—C120	−179.0 (5)	C37—N38—C39—C310	−172 (4)
C26—C21—C22—C23	−1.0 (5)	N38—C39—C310—N311	−64 (4)
C27—C21—C22—C23	178.6 (3)	C312—N311—C310—C39	178 (3)
C21—C22—C23—C24	3.3 (5)	C310—N311—C312—C313	−75 (4)
C21—C22—C23—C28	−175.4 (3)	C310—N311—C312—C318	47 (4)
C22—C23—C24—C25	−2.6 (5)	C310—N311—C312—C319	164 (3)
C28—C23—C24—C25	176.1 (3)	N311—C312—C313—C314	−63 (3)
C23—C24—C25—C26	−0.5 (5)	C318—C312—C313—C314	176 (2)
C23—C24—C25—C29	−180.0 (3)	C319—C312—C313—C314	54 (3)
C24—C25—C26—C21	3.0 (5)	C32—N31—C314—C313	−178.2 (19)
C29—C25—C26—C21	−177.6 (3)	C32—N31—C314—C320	64 (3)
C22—C21—C26—C25	−2.2 (5)	C312—C313—C314—N31	62 (3)
C27—C21—C26—C25	178.2 (3)	C312—C313—C314—C320	−176 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14E···N18	0.92	2.17	2.878 (9)	133
N111—H11C···N11	0.92	2.24	2.880 (5)	126
N11—H11A···O21	0.92	2.08	3.002 (6)	179
N14—H14F···O24^i	0.92	2.03	2.853 (9)	148
N18—H18A···O21	0.92	2.16	3.071 (4)	169
N111—H11D···O26^ii	0.92	1.85	2.695 (3)	152
O22—H222···O22^iii	0.85	1.62	2.458 (4)	171
O23—H223···O23^iv	1.10	1.35	2.442 (4)	170
O41—H41···O25	0.84	1.81	2.643 (4)	172
N34—H34A···N38	0.92	2.33	2.94 (4)	124
N311—H31C···N31	0.92	2.11	2.84 (5)	136
N31—H31A···O24^i	0.92	2.47	3.34 (2)	158
N34—H34B···O25^ii	0.92	1.91	2.75 (2)	152
N38—H38A···O24^i	0.92	1.91	2.82 (7)	170
N311—H31D···O21	0.92	2.29	3.10 (4)	147

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