Adducts of 1,4,8,11-tetraazacyclotetradecane with carboxylic acids: hydrogen-bonded supramolecular structures in two or three dimensions

Four solvated salt-type adducts derived from cyclam (1,4,8,11-tetraazacyclotetradecane) and carboxylic acids have been structurally characterized. In the salt derived from adamantane-1-carboxylic acid, 4,11-diaza-1,8-diazoniacyclotetra­decane bis(adamantane-1-carboxylate) tetrahydrate, (1) (mono­clinic, P2₁/c, Z′ = 0.5), where the cation lies across a centre of inversion, the anions and the water molecules form chains of edge-fused (8) and (16) rings, which are linked into sheets by the cations. In the 4-aminobenzoate salt, 4,11-diaza-1,8-diazoniacyclotetradecane bis(4-aminobenzo­ate) mono­hydrate, (2) (monoclinic, C2/c, Z′ = 0.5), where the cation lies across a centre of inversion and the water molecule lies across a twofold rotation axis, the cations and anions generate a three-dimensional framework, readily analysed in terms of two distinct two-dimensional substructures, viz. (10) sheets of (46) rings, and pairwise interwoven (100) sheets, reinforced by water molecules. The 3-hydroxybenzoate salt, 4,11-diaza-1,8-diazoniacyclotetradecane bis(3-hydroxybenzo­ate) dihydrate, (3) (monoclinic, Pc, Z′ = 1), contains a three-dimensional framework constructed from anions and water molecules only, which encapsulates large voids and within which the cations are linked to the anion–water framework via N—H...O hydrogen bonds. There are two independent cations in 4,11-diaza-1,8-diazoniacyclotetradecane 5-hydroxy­isophthalate(2−) methanol solvate, (4) (monoclinic, P2₁/c, Z′ = 1), both lying across centres of inversion but with entirely different configurations. The anions alone form simple chains, and these chains are linked by the two types of cation into a three-dimensional framework from which the methanol mol­ecules are pendent. Comparisons are made with carboxyl­ate complexes of the [Ni(cyclam)]²⁺ cation and with carb­oxyl­ate salts derived from meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane.

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

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

Figures

In full text version

(I) Cyclam/adamantane-1-carboxylic acid/water (1/2/4)

Crystal data

C10H26N4·2(C11H15O2)·4(H2O)	F(000) = 696
Mr = 632.87	Dx = 1.254 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3796 reflections
a = 8.8604 (2) Å	θ = 2.9–27.5°
b = 6.8025 (1) Å	µ = 0.09 mm^−1
c = 27.8239 (6) Å	T = 150 K
β = 91.044 (1)°	Block, colourless
V = 1676.75 (6) Å^3	0.35 × 0.25 × 0.22 mm
Z = 2

Data collection

Kappa-CCD diffractometer	2910 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.035
Graphite monochromator	θmax = 27.5°, θmin = 2.9°
ϕ scans, and ω scans with κ offsets	h = 0→11
10461 measured reflections	k = 0→8
3796 independent reflections	l = −36→36

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) = 0.124	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.6247P] where P = (Fo^2 + 2Fc^2)/3
3796 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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

	x	y	z	Uiso*/Ueq
N11	0.81889 (13)	−0.06955 (18)	0.45866 (4)	0.0301 (3)
N14	0.86805 (14)	0.10443 (18)	0.55534 (4)	0.0296 (3)
C12	0.70545 (16)	0.0458 (2)	0.48525 (6)	0.0335 (3)
C13	0.72543 (16)	0.0187 (2)	0.53916 (5)	0.0332 (3)
C15	0.90131 (17)	0.0665 (2)	0.60637 (5)	0.0329 (3)
C16	1.05839 (17)	0.1420 (2)	0.61920 (5)	0.0344 (3)
C17	1.18354 (17)	0.0317 (2)	0.59407 (5)	0.0321 (3)
O1	0.60518 (13)	0.48842 (19)	0.56160 (4)	0.0417 (3)
O2	0.82011 (12)	0.54080 (18)	0.60192 (4)	0.0402 (3)
C1	0.59123 (15)	0.5408 (2)	0.64657 (5)	0.0231 (3)
C2	0.69536 (16)	0.5546 (2)	0.69106 (5)	0.0288 (3)
C3	0.49453 (16)	0.7287 (2)	0.64317 (5)	0.0269 (3)
C4	0.48522 (16)	0.3639 (2)	0.65230 (5)	0.0268 (3)
C5	0.39152 (16)	0.3865 (2)	0.69765 (5)	0.0289 (3)
C6	0.49681 (17)	0.4000 (2)	0.74184 (5)	0.0317 (3)
C7	0.60149 (16)	0.5779 (2)	0.73651 (5)	0.0302 (3)
C8	0.50682 (17)	0.7659 (2)	0.73270 (5)	0.0325 (3)
C9	0.40094 (16)	0.7521 (2)	0.68864 (5)	0.0295 (3)
C10	0.29635 (16)	0.5743 (2)	0.69374 (5)	0.0323 (3)
C11	0.68036 (16)	0.5210 (2)	0.59995 (5)	0.0277 (3)
O3	0.31055 (13)	0.43994 (16)	0.52907 (4)	0.0371 (3)
O4	0.01236 (13)	0.6691 (2)	0.53519 (4)	0.0497 (3)
H11A	0.8019	−0.2012	0.4638	0.036*
H11B	0.9135	−0.0403	0.4709	0.036*
H14	0.8651	0.2380	0.5503	0.036*
H12A	0.6028	0.0032	0.4752	0.040*
H12B	0.7159	0.1868	0.4772	0.040*
H13A	0.6410	0.0828	0.5559	0.040*
H13B	0.7240	−0.1232	0.5471	0.040*
H15A	0.8957	−0.0764	0.6128	0.039*
H15B	0.8258	0.1335	0.6264	0.039*
H16A	1.0644	0.2829	0.6106	0.041*
H16B	1.0747	0.1310	0.6544	0.041*
H17A	1.2824	0.0728	0.6079	0.039*
H17B	1.1719	−0.1110	0.5999	0.039*
H2A	0.7639	0.6687	0.6879	0.035*
H2B	0.7579	0.4343	0.6937	0.035*
H3A	0.5609	0.8446	0.6394	0.032*
H3B	0.4264	0.7211	0.6146	0.032*
H4A	0.4171	0.3541	0.6238	0.032*
H4B	0.5454	0.2415	0.6544	0.032*
H5	0.3234	0.2702	0.7009	0.035*
H6A	0.5576	0.2783	0.7448	0.038*
H6B	0.4365	0.4142	0.7712	0.038*
H7	0.6706	0.5866	0.7653	0.036*
H8A	0.5740	0.8813	0.7296	0.039*
H8B	0.4470	0.7825	0.7621	0.039*
H9	0.3390	0.8746	0.6861	0.035*
H10A	0.2273	0.5658	0.6654	0.039*
H10B	0.2346	0.5893	0.7228	0.039*
H31	0.3309	0.4591	0.4960	0.056*
H32	0.4068	0.4490	0.5445	0.056*
H41	0.0814	0.5782	0.5353	0.075*
H42	−0.0447	0.6160	0.5567	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0295 (6)	0.0308 (7)	0.0300 (6)	−0.0007 (5)	0.0012 (5)	0.0012 (5)
N14	0.0339 (6)	0.0267 (6)	0.0282 (6)	−0.0010 (5)	0.0025 (5)	0.0007 (5)
C12	0.0255 (7)	0.0349 (8)	0.0402 (8)	0.0007 (6)	0.0035 (6)	−0.0019 (7)
C13	0.0304 (7)	0.0336 (8)	0.0358 (8)	−0.0017 (6)	0.0069 (6)	−0.0022 (7)
C15	0.0384 (8)	0.0328 (8)	0.0276 (7)	0.0000 (7)	0.0071 (6)	−0.0002 (6)
C16	0.0434 (9)	0.0347 (8)	0.0252 (7)	−0.0026 (7)	0.0008 (6)	−0.0008 (6)
C17	0.0350 (8)	0.0330 (8)	0.0282 (7)	−0.0034 (7)	−0.0035 (6)	0.0019 (6)
O1	0.0465 (6)	0.0566 (8)	0.0223 (5)	−0.0091 (6)	0.0075 (5)	−0.0043 (5)
O2	0.0318 (6)	0.0525 (7)	0.0366 (6)	0.0046 (5)	0.0117 (5)	0.0052 (5)
C1	0.0252 (6)	0.0230 (7)	0.0211 (6)	−0.0005 (5)	0.0027 (5)	0.0002 (5)
C2	0.0260 (7)	0.0343 (8)	0.0261 (7)	0.0002 (6)	0.0007 (5)	0.0002 (6)
C3	0.0320 (7)	0.0239 (7)	0.0249 (6)	0.0020 (6)	0.0022 (5)	0.0016 (5)
C4	0.0332 (7)	0.0235 (7)	0.0238 (6)	−0.0015 (6)	0.0043 (6)	−0.0017 (6)
C5	0.0321 (7)	0.0292 (7)	0.0258 (7)	−0.0071 (6)	0.0066 (6)	0.0004 (6)
C6	0.0405 (8)	0.0319 (8)	0.0228 (7)	0.0018 (7)	0.0064 (6)	0.0040 (6)
C7	0.0315 (7)	0.0380 (8)	0.0211 (6)	0.0004 (6)	−0.0014 (6)	−0.0014 (6)
C8	0.0385 (8)	0.0310 (8)	0.0281 (7)	−0.0031 (6)	0.0060 (6)	−0.0076 (6)
C9	0.0316 (7)	0.0275 (7)	0.0295 (7)	0.0067 (6)	0.0041 (6)	−0.0011 (6)
C10	0.0269 (7)	0.0406 (9)	0.0296 (7)	0.0004 (6)	0.0056 (6)	−0.0031 (6)
C11	0.0340 (7)	0.0232 (7)	0.0263 (7)	0.0010 (6)	0.0081 (6)	0.0022 (6)
O3	0.0430 (6)	0.0394 (6)	0.0290 (5)	−0.0100 (5)	0.0051 (4)	0.0007 (5)
O4	0.0463 (7)	0.0526 (8)	0.0509 (7)	−0.0028 (6)	0.0179 (6)	0.0089 (6)

Geometric parameters (Å, º)

N11—C12	1.4835 (19)	C2—H2A	0.99
N11—C17^i	1.4892 (18)	C2—H2B	0.99
N11—H11A	0.92	C3—C9	1.5334 (19)
N11—H11B	0.92	C3—H3A	0.99
N14—C13	1.4558 (19)	C3—H3B	0.99
N14—C15	1.4676 (18)	C4—C5	1.5308 (18)
N14—H14	0.92	C4—H4A	0.99
C12—C13	1.518 (2)	C4—H4B	0.99
C12—H12A	0.99	C5—C6	1.533 (2)
C12—H12B	0.99	C5—C10	1.534 (2)
C13—H13A	0.99	C5—H5	1.00
C13—H13B	0.99	C6—C7	1.534 (2)
C15—C16	1.520 (2)	C6—H6A	0.99
C15—H15A	0.99	C6—H6B	0.99
C15—H15B	0.99	C7—C8	1.532 (2)
C16—C17	1.520 (2)	C7—H7	1.00
C16—H16A	0.99	C8—C9	1.533 (2)
C16—H16B	0.99	C8—H8A	0.99
C17—N11^i	1.4892 (18)	C8—H8B	0.99
C17—H17A	0.99	C9—C10	1.532 (2)
C17—H17B	0.99	C9—H9	1.00
O1—C11	1.2670 (18)	C10—H10A	0.99
O2—C11	1.2458 (18)	C10—H10B	0.99
C1—C2	1.5332 (19)	O3—H31	0.95
C1—C4	1.5366 (19)	O3—H32	0.95
C1—C11	1.5369 (18)	O4—H41	0.87
C1—C3	1.5410 (19)	O4—H42	0.87
C2—C7	1.5344 (19)
C12—N11—C17^i	113.71 (12)	C9—C3—H3A	109.6
C12—N11—H11A	108.8	C1—C3—H3A	109.6
C17^i—N11—H11A	108.8	C9—C3—H3B	109.6
C12—N11—H11B	108.8	C1—C3—H3B	109.6
C17^i—N11—H11B	108.8	H3A—C3—H3B	108.2
H11A—N11—H11B	107.7	C5—C4—C1	110.41 (11)
C13—N14—C15	112.75 (12)	C5—C4—H4A	109.6
C13—N14—H14	109.0	C1—C4—H4A	109.6
C15—N14—H14	109.0	C5—C4—H4B	109.6
N11—C12—C13	111.13 (12)	C1—C4—H4B	109.6
N11—C12—H12A	109.4	H4A—C4—H4B	108.1
C13—C12—H12A	109.4	C4—C5—C6	109.63 (12)
N11—C12—H12B	109.4	C4—C5—C10	109.31 (11)
C13—C12—H12B	109.4	C6—C5—C10	109.44 (12)
H12A—C12—H12B	108.0	C4—C5—H5	109.5
N14—C13—C12	109.98 (12)	C6—C5—H5	109.5
N14—C13—H13A	109.7	C10—C5—H5	109.5
C12—C13—H13A	109.7	C5—C6—C7	109.27 (11)
N14—C13—H13B	109.7	C5—C6—H6A	109.8
C12—C13—H13B	109.7	C7—C6—H6A	109.8
H13A—C13—H13B	108.2	C5—C6—H6B	109.8
N14—C15—C16	109.57 (12)	C7—C6—H6B	109.8
N14—C15—H15A	109.8	H6A—C6—H6B	108.3
C16—C15—H15A	109.8	C8—C7—C6	109.52 (12)
N14—C15—H15B	109.8	C8—C7—C2	109.48 (12)
C16—C15—H15B	109.8	C6—C7—C2	109.63 (12)
H15A—C15—H15B	108.2	C8—C7—H7	109.4
C17—C16—C15	113.45 (13)	C6—C7—H7	109.4
C17—C16—H16A	108.9	C2—C7—H7	109.4
C15—C16—H16A	108.9	C7—C8—C9	109.31 (11)
C17—C16—H16B	108.9	C7—C8—H8A	109.8
C15—C16—H16B	108.9	C9—C8—H8A	109.8
H16A—C16—H16B	107.7	C7—C8—H8B	109.8
N11^i—C17—C16	111.74 (12)	C9—C8—H8B	109.8
N11^i—C17—H17A	109.3	H8A—C8—H8B	108.3
C16—C17—H17A	109.3	C10—C9—C8	109.67 (12)
N11^i—C17—H17B	109.3	C10—C9—C3	109.39 (12)
C16—C17—H17B	109.3	C8—C9—C3	109.50 (11)
H17A—C17—H17B	107.9	C10—C9—H9	109.4
C2—C1—C4	108.92 (11)	C8—C9—H9	109.4
C2—C1—C11	112.08 (11)	C3—C9—H9	109.4
C4—C1—C11	110.07 (11)	C9—C10—C5	109.36 (11)
C2—C1—C3	108.93 (11)	C9—C10—H10A	109.8
C4—C1—C3	108.41 (11)	C5—C10—H10A	109.8
C11—C1—C3	108.35 (11)	C9—C10—H10B	109.8
C1—C2—C7	110.15 (11)	C5—C10—H10B	109.8
C1—C2—H2A	109.6	H10A—C10—H10B	108.3
C7—C2—H2A	109.6	O2—C11—O1	124.24 (13)
C1—C2—H2B	109.6	O2—C11—C1	118.63 (12)
C7—C2—H2B	109.6	O1—C11—C1	117.12 (12)
H2A—C2—H2B	108.1	H31—O3—H32	104.1
C9—C3—C1	110.10 (11)	H41—O4—H42	96.9
C17^i—N11—C12—C13	−173.49 (12)	C5—C6—C7—C2	−59.81 (15)
C15—N14—C13—C12	−174.43 (12)	C1—C2—C7—C8	−60.16 (15)
N11—C12—C13—N14	66.53 (16)	C1—C2—C7—C6	60.00 (15)
C13—N14—C15—C16	174.22 (13)	C6—C7—C8—C9	−60.07 (15)
N14—C15—C16—C17	−65.65 (17)	C2—C7—C8—C9	60.16 (15)
C15—C16—C17—N11^i	68.14 (17)	C7—C8—C9—C10	59.93 (15)
C4—C1—C2—C7	−58.97 (15)	C7—C8—C9—C3	−60.11 (15)
C11—C1—C2—C7	178.99 (12)	C1—C3—C9—C10	−60.36 (14)
C3—C1—C2—C7	59.11 (15)	C1—C3—C9—C8	59.86 (15)
C2—C1—C3—C9	−59.01 (14)	C8—C9—C10—C5	−59.94 (15)
C4—C1—C3—C9	59.39 (14)	C3—C9—C10—C5	60.17 (15)
C11—C1—C3—C9	178.82 (11)	C4—C5—C10—C9	−60.00 (15)
C2—C1—C4—C5	58.94 (14)	C6—C5—C10—C9	60.08 (14)
C11—C1—C4—C5	−177.80 (11)	C2—C1—C11—O2	−8.16 (18)
C3—C1—C4—C5	−59.46 (14)	C4—C1—C11—O2	−129.54 (14)
C1—C4—C5—C6	−59.71 (15)	C3—C1—C11—O2	112.07 (14)
C1—C4—C5—C10	60.26 (15)	C2—C1—C11—O1	173.02 (13)
C4—C5—C6—C7	59.63 (15)	C4—C1—C11—O1	51.63 (16)
C10—C5—C6—C7	−60.25 (15)	C3—C1—C11—O1	−66.75 (16)
C5—C6—C7—C8	60.32 (15)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···O1^ii	0.95	1.75	2.689 (2)	171
O3—H32···O1	0.95	1.83	2.767 (2)	168
O4—H41···O3	0.87	2.25	3.075 (2)	159
O4—H42···O2^iii	0.87	1.83	2.688 (2)	171
N11—H11A···O3^iv	0.92	1.92	2.792 (2)	158
N11—H11B···N14^i	0.92	2.13	2.818 (2)	131
N14—H14···O2	0.92	2.55	3.270 (2)	136

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

(II) Cyclam/4-aminobenzoic acid/water (1/2/1)

Crystal data

C10H26N4·2(C7H6NO2)·H2O	F(000) = 1064
Mr = 492.62	Dx = 1.215 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3016 reflections
a = 19.6462 (8) Å	θ = 2.7–27.3°
b = 9.0374 (4) Å	µ = 0.09 mm^−1
c = 15.2051 (7) Å	T = 150 K
β = 94.127 (2)°	Plate, colourless
V = 2692.7 (2) Å^3	0.32 × 0.29 × 0.14 mm
Z = 4

Data collection

Kappa-CCD diffractometer	2156 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.046
Graphite monochromator	θmax = 27.3°, θmin = 2.7°
ϕ scans, and ω scans with κ offsets	h = 0→25
12532 measured reflections	k = 0→11
3016 independent reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0325P)^2 + 1.3517P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3016 reflections	Δρmax = 0.20 e Å^−3
160 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0053 (11)

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

	x	y	z	Uiso*/Ueq
N1	0.42773 (7)	0.62905 (15)	0.55994 (8)	0.0398 (3)
C2	0.38060 (8)	0.5088 (2)	0.58261 (11)	0.0448 (4)
C3	0.37065 (8)	0.4001 (2)	0.50743 (12)	0.0473 (4)
N4	0.43578 (7)	0.33453 (15)	0.48770 (9)	0.0425 (3)
C5	0.42828 (9)	0.2312 (2)	0.41292 (12)	0.0517 (5)
C6	0.49585 (9)	0.1631 (2)	0.39323 (12)	0.0502 (4)
C7	0.54826 (9)	0.27379 (19)	0.36504 (11)	0.0457 (4)
O1	0.45163 (6)	0.76226 (14)	0.36951 (7)	0.0469 (3)
O2	0.35882 (6)	0.80238 (13)	0.44065 (7)	0.0451 (3)
N14	0.26661 (7)	1.10796 (17)	0.07289 (9)	0.0504 (4)
C11	0.35859 (7)	0.88730 (17)	0.29302 (10)	0.0345 (3)
C12	0.38777 (8)	0.88507 (16)	0.21238 (10)	0.0357 (4)
C13	0.35641 (8)	0.95465 (17)	0.13929 (10)	0.0378 (4)
C14	0.29559 (8)	1.03384 (18)	0.14536 (10)	0.0388 (4)
C15	0.26634 (8)	1.0356 (2)	0.22606 (11)	0.0479 (4)
C16	0.29729 (8)	0.9625 (2)	0.29786 (11)	0.0453 (4)
C17	0.39247 (8)	0.81222 (17)	0.37225 (10)	0.0366 (4)
O3	0.5000	0.56935 (18)	0.2500	0.0516 (5)
H1A	0.4061	0.6868	0.5167	0.048*
H1B	0.4652	0.5872	0.5368	0.048*
H2A	0.3360	0.5517	0.5954	0.054*
H2B	0.3996	0.4568	0.6362	0.054*
H3A	0.3389	0.3211	0.5233	0.057*
H3B	0.3501	0.4515	0.4544	0.057*
H4	0.4541	0.2850	0.5367	0.051*
H5A	0.4089	0.2846	0.3601	0.062*
H5B	0.3960	0.1517	0.4265	0.062*
H6A	0.4876	0.0887	0.3459	0.060*
H6B	0.5150	0.1106	0.4465	0.060*
H7A	0.5876	0.2201	0.3433	0.055*
H7B	0.5277	0.3353	0.3162	0.055*
H14A	0.2286	1.1582	0.0769	0.060*
H14B	0.2861	1.1051	0.0226	0.060*
H12	0.4299	0.8350	0.2074	0.043*
H13	0.3763	0.9487	0.0843	0.045*
H15	0.2248	1.0875	0.2317	0.057*
H16	0.2761	0.9637	0.3521	0.054*
H3	0.4787	0.6317	0.2902	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0416 (7)	0.0398 (7)	0.0375 (7)	0.0026 (6)	−0.0011 (5)	0.0056 (6)
C2	0.0396 (9)	0.0470 (10)	0.0478 (9)	0.0000 (7)	0.0035 (7)	0.0099 (8)
C3	0.0395 (9)	0.0472 (10)	0.0539 (10)	−0.0022 (8)	−0.0056 (7)	0.0072 (8)
N4	0.0412 (7)	0.0413 (8)	0.0434 (7)	0.0012 (6)	−0.0073 (6)	0.0047 (6)
C5	0.0519 (10)	0.0480 (10)	0.0533 (10)	−0.0045 (8)	−0.0092 (8)	−0.0035 (8)
C6	0.0579 (11)	0.0424 (10)	0.0488 (10)	0.0000 (8)	−0.0055 (8)	−0.0023 (8)
C7	0.0588 (11)	0.0390 (9)	0.0386 (9)	0.0071 (8)	−0.0019 (7)	0.0016 (7)
O1	0.0414 (6)	0.0611 (8)	0.0379 (6)	0.0108 (6)	−0.0002 (5)	0.0088 (5)
O2	0.0452 (6)	0.0555 (7)	0.0346 (6)	0.0043 (5)	0.0035 (5)	0.0101 (5)
N14	0.0440 (8)	0.0629 (10)	0.0438 (8)	0.0083 (7)	−0.0001 (6)	0.0189 (7)
C11	0.0358 (8)	0.0343 (8)	0.0329 (8)	−0.0030 (6)	−0.0012 (6)	0.0047 (6)
C12	0.0400 (8)	0.0310 (8)	0.0355 (8)	0.0016 (6)	0.0001 (6)	0.0017 (6)
C13	0.0456 (9)	0.0356 (8)	0.0321 (8)	−0.0004 (7)	0.0025 (6)	0.0017 (6)
C14	0.0375 (8)	0.0390 (9)	0.0388 (8)	−0.0033 (7)	−0.0039 (6)	0.0080 (7)
C15	0.0355 (8)	0.0594 (11)	0.0491 (10)	0.0088 (8)	0.0057 (7)	0.0159 (8)
C16	0.0388 (9)	0.0579 (11)	0.0399 (8)	0.0045 (8)	0.0070 (7)	0.0128 (8)
C17	0.0386 (8)	0.0377 (8)	0.0329 (8)	−0.0024 (7)	−0.0012 (6)	0.0031 (6)
O3	0.0653 (11)	0.0345 (9)	0.0534 (10)	0.000	−0.0071 (8)	0.000

Geometric parameters (Å, º)

N1—C2	1.484 (2)	C7—H7A	0.99
N1—C7^i	1.489 (2)	C7—H7B	0.99
N1—H1A	0.92	O1—C17	1.2504 (19)
N1—H1B	0.92	O2—C17	1.2751 (19)
C2—C3	1.509 (2)	N14—C14	1.3773 (19)
C2—H2A	0.99	N14—H14A	0.88
C2—H2B	0.99	N14—H14B	0.88
C3—N4	1.461 (2)	C11—C16	1.390 (2)
C3—H3A	0.99	C11—C12	1.391 (2)
C3—H3B	0.99	C11—C17	1.496 (2)
N4—C5	1.470 (2)	C12—C13	1.383 (2)
N4—H4	0.92	C12—H12	0.95
C5—C6	1.513 (3)	C13—C14	1.401 (2)
C5—H5A	0.99	C13—H13	0.95
C5—H5B	0.99	C14—C15	1.392 (2)
C6—C7	1.519 (3)	C15—C16	1.379 (2)
C6—H6A	0.99	C15—H15	0.95
C6—H6B	0.99	C16—H16	0.95
C7—N1^i	1.489 (2)	O3—H3	0.95
C2—N1—C7^i	114.98 (13)	H6A—C6—H6B	107.6
C2—N1—H1A	108.5	N1^i—C7—C6	110.85 (14)
C7^i—N1—H1A	108.5	N1^i—C7—H7A	109.5
C2—N1—H1B	108.5	C6—C7—H7A	109.5
C7^i—N1—H1B	108.5	N1^i—C7—H7B	109.5
H1A—N1—H1B	107.5	C6—C7—H7B	109.5
N1—C2—C3	110.46 (14)	H7A—C7—H7B	108.1
N1—C2—H2A	109.6	C14—N14—H14A	120.0
C3—C2—H2A	109.6	C14—N14—H14B	120.0
N1—C2—H2B	109.6	H14A—N14—H14B	120.0
C3—C2—H2B	109.6	C16—C11—C12	117.88 (14)
H2A—C2—H2B	108.1	C16—C11—C17	121.09 (14)
N4—C3—C2	110.61 (13)	C12—C11—C17	121.03 (14)
N4—C3—H3A	109.5	C13—C12—C11	120.93 (14)
C2—C3—H3A	109.5	C13—C12—H12	119.5
N4—C3—H3B	109.5	C11—C12—H12	119.5
C2—C3—H3B	109.5	C12—C13—C14	120.80 (15)
H3A—C3—H3B	108.1	C12—C13—H13	119.6
C3—N4—C5	112.09 (13)	C14—C13—H13	119.6
C3—N4—H4	109.2	N14—C14—C15	121.77 (15)
C5—N4—H4	109.2	N14—C14—C13	120.07 (15)
N4—C5—C6	111.78 (14)	C15—C14—C13	118.16 (14)
N4—C5—H5A	109.3	C16—C15—C14	120.38 (15)
C6—C5—H5A	109.3	C16—C15—H15	119.8
N4—C5—H5B	109.3	C14—C15—H15	119.8
C6—C5—H5B	109.3	C15—C16—C11	121.80 (15)
H5A—C5—H5B	107.9	C15—C16—H16	119.1
C5—C6—C7	114.21 (15)	C11—C16—H16	119.1
C5—C6—H6A	108.7	O1—C17—O2	122.67 (14)
C7—C6—H6A	108.7	O1—C17—C11	119.85 (13)
C5—C6—H6B	108.7	O2—C17—C11	117.49 (14)
C7—C6—H6B	108.7
C7^i—N1—C2—C3	−168.79 (13)	C12—C13—C14—C15	−2.5 (2)
N1—C2—C3—N4	59.59 (17)	N14—C14—C15—C16	−178.78 (16)
C2—C3—N4—C5	−178.29 (14)	C13—C14—C15—C16	0.8 (3)
C3—N4—C5—C6	−179.67 (15)	C14—C15—C16—C11	1.0 (3)
N4—C5—C6—C7	−63.0 (2)	C12—C11—C16—C15	−1.2 (3)
C5—C6—C7—N1^i	69.14 (18)	C17—C11—C16—C15	178.25 (16)
C16—C11—C12—C13	−0.5 (2)	C16—C11—C17—O1	−170.55 (15)
C17—C11—C12—C13	−179.94 (14)	C12—C11—C17—O1	8.9 (2)
C11—C12—C13—C14	2.3 (2)	C16—C11—C17—O2	9.4 (2)
C12—C13—C14—N14	177.12 (15)	C12—C11—C17—O2	−171.20 (15)

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
O3—H3···O1	0.95	1.79	2.7374 (16)	171
N1—H1A···O2	0.92	1.77	2.6875 (17)	175
N1—H1B···N4^i	0.92	2.13	2.8467 (19)	134
N4—H4···O1^i	0.92	2.29	3.1113 (16)	148
N14—H14A···O2^ii	0.88	2.16	3.0215 (19)	167
N14—H14B···O2^iii	0.88	2.13	2.9163 (19)	148
C2—H2B···O3^i	0.99	2.54	3.409 (2)	146
C7—H7B···O3	0.99	2.39	3.295 (2)	152

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

(III) Cyclam/3-hydroxybenzoic acid/water (1/2/2)

Crystal data

C10H26N4·2(C7H5O3)·2(H2O)	F(000) = 552
Mr = 512.60	Dx = 1.276 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 3059 reflections
a = 9.1490 (2) Å	θ = 2.9–27.7°
b = 12.8557 (4) Å	µ = 0.10 mm^−1
c = 12.4022 (4) Å	T = 150 K
β = 113.8540 (19)°	Block, colourless
V = 1334.10 (7) Å^3	0.30 × 0.28 × 0.22 mm
Z = 2

Data collection

Kappa-CCD diffractometer	2693 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.039
Graphite monochromator	θmax = 27.7°, θmin = 2.9°
ϕ scans, and ω scans with κ offsets	h = 0→11
9540 measured reflections	k = −16→0
3059 independent reflections	l = −16→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0769P)^2 + 0.064P] where P = (Fo^2 + 2Fc^2)/3
3059 reflections	(Δ/σ)max = 0.006
337 parameters	Δρmax = 0.28 e Å^−3
2 restraints	Δρmin = −0.22 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.5723 (2)	0.32367 (15)	0.57229 (17)	0.0239 (4)
N4	0.7056 (2)	0.12662 (15)	0.69316 (18)	0.0251 (4)
N8	0.6276 (2)	0.16803 (15)	0.88924 (18)	0.0243 (4)
N11	0.4963 (2)	0.36556 (15)	0.76843 (18)	0.0251 (4)
C2	0.5972 (3)	0.2305 (2)	0.5107 (2)	0.0291 (5)
C3	0.7380 (3)	0.1685 (2)	0.5947 (2)	0.0296 (5)
C5	0.8480 (3)	0.0760 (2)	0.7802 (2)	0.0311 (5)
C6	0.8194 (3)	0.0330 (2)	0.8843 (2)	0.0315 (5)
C7	0.7843 (3)	0.1162 (2)	0.9581 (2)	0.0299 (5)
C9	0.5960 (3)	0.26053 (19)	0.9486 (2)	0.0268 (5)
C10	0.4563 (3)	0.32158 (19)	0.8624 (2)	0.0287 (5)
C12	0.3597 (3)	0.4242 (2)	0.6829 (2)	0.0314 (5)
C13	0.3947 (3)	0.46555 (19)	0.5803 (2)	0.0330 (6)
C14	0.4203 (3)	0.3804 (2)	0.5046 (2)	0.0301 (5)
O21	0.8359 (2)	0.43950 (14)	0.60223 (15)	0.0312 (4)
O22	0.69780 (19)	0.45404 (14)	0.40887 (15)	0.0284 (4)
O23	1.0635 (2)	0.66554 (15)	0.27524 (17)	0.0349 (4)
C21	0.9370 (3)	0.55276 (17)	0.4965 (2)	0.0223 (4)
C22	0.9444 (2)	0.57165 (18)	0.3878 (2)	0.0241 (5)
C23	1.0500 (3)	0.64649 (19)	0.3795 (2)	0.0257 (5)
C24	1.1453 (3)	0.70285 (19)	0.4788 (2)	0.0288 (5)
C25	1.1381 (3)	0.6836 (2)	0.5867 (2)	0.0302 (5)
C26	1.0345 (3)	0.60751 (19)	0.5959 (2)	0.0260 (5)
C27	0.8164 (3)	0.47597 (17)	0.5029 (2)	0.0234 (5)
O31	0.4749 (2)	−0.04641 (15)	0.54280 (16)	0.0351 (4)
O32	0.3921 (2)	−0.02004 (14)	0.35045 (15)	0.0328 (4)
O33	−0.0767 (2)	0.21645 (16)	0.23956 (16)	0.0363 (4)
C31	0.2539 (3)	0.06855 (18)	0.4502 (2)	0.0230 (4)
C32	0.1468 (3)	0.11166 (18)	0.3459 (2)	0.0243 (5)
C33	0.0303 (3)	0.18236 (18)	0.3467 (2)	0.0264 (5)
C34	0.0267 (3)	0.2115 (2)	0.4536 (2)	0.0283 (5)
C35	0.1333 (3)	0.1674 (2)	0.5581 (2)	0.0304 (5)
C36	0.2469 (3)	0.09532 (19)	0.5575 (2)	0.0266 (5)
C37	0.3820 (3)	−0.00625 (19)	0.4484 (2)	0.0247 (5)
O1	0.6614 (2)	0.30803 (15)	0.23733 (18)	0.0382 (4)
O2	0.4509 (3)	0.14876 (15)	0.22633 (17)	0.0403 (5)
H1A	0.6566	0.3686	0.5875	0.029*
H1B	0.5729	0.3033	0.6436	0.029*
H4	0.6234	0.0792	0.6648	0.030*
H8A	0.6250	0.1881	0.8173	0.029*
H8B	0.5469	0.1205	0.8755	0.029*
H11A	0.5829	0.4091	0.8010	0.030*
H2A	0.6178	0.2524	0.4416	0.035*
H2B	0.4998	0.1867	0.4823	0.035*
H3A	0.7609	0.1104	0.5515	0.036*
H3B	0.8337	0.2137	0.6261	0.036*
H5A	0.9367	0.1270	0.8093	0.037*
H5B	0.8808	0.0185	0.7417	0.037*
H6A	0.9150	−0.0067	0.9356	0.038*
H6B	0.7283	−0.0160	0.8544	0.038*
H7A	0.7817	0.0839	1.0298	0.036*
H7B	0.8707	0.1688	0.9832	0.036*
H9A	0.6922	0.3053	0.9794	0.032*
H9B	0.5719	0.2378	1.0159	0.032*
H10A	0.3623	0.2753	0.8275	0.034*
H10B	0.4285	0.3784	0.9046	0.034*
H12A	0.3344	0.4832	0.7237	0.038*
H12B	0.2648	0.3782	0.6518	0.038*
H13A	0.3045	0.5099	0.5300	0.040*
H13B	0.4915	0.5097	0.6121	0.040*
H14A	0.3295	0.3310	0.4797	0.036*
H14B	0.4246	0.4115	0.4329	0.036*
H23	0.9995	0.6273	0.2222	0.052*
H22A	0.8779	0.5337	0.3198	0.024 (7)*
H24	1.2156	0.7547	0.4728	0.038 (8)*
H25	1.2036	0.7222	0.6544	0.034 (8)*
H26	1.0310	0.5934	0.6700	0.041 (8)*
H33	−0.1509	0.2489	0.2482	0.076 (14)*
H32	0.1521	0.0933	0.2733	0.035 (8)*
H34	−0.0488	0.2615	0.4551	0.044 (9)*
H35	0.1288	0.1866	0.6307	0.034 (8)*
H36	0.3187	0.0647	0.6290	0.029 (7)*
H11	0.5914	0.2649	0.2354	0.056*
H12	0.6695	0.3545	0.2870	0.056*
H21	0.4431	0.1188	0.1641	0.056*
H22	0.4218	0.1081	0.2668	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0265 (9)	0.0255 (9)	0.0214 (10)	−0.0013 (7)	0.0115 (8)	0.0011 (7)
N4	0.0266 (9)	0.0239 (10)	0.0272 (10)	−0.0011 (7)	0.0133 (8)	−0.0003 (8)
N8	0.0290 (9)	0.0236 (9)	0.0216 (10)	−0.0023 (7)	0.0117 (8)	0.0015 (7)
N11	0.0273 (9)	0.0249 (10)	0.0255 (10)	0.0004 (8)	0.0133 (8)	0.0005 (8)
C2	0.0417 (13)	0.0266 (12)	0.0245 (12)	−0.0044 (10)	0.0190 (10)	−0.0025 (9)
C3	0.0360 (12)	0.0290 (12)	0.0319 (13)	0.0017 (9)	0.0220 (11)	−0.0021 (10)
C5	0.0307 (11)	0.0301 (12)	0.0344 (14)	0.0064 (9)	0.0151 (10)	0.0022 (10)
C6	0.0342 (12)	0.0286 (12)	0.0327 (14)	0.0059 (9)	0.0144 (10)	0.0066 (10)
C7	0.0269 (11)	0.0338 (13)	0.0261 (12)	0.0031 (9)	0.0076 (10)	0.0030 (10)
C9	0.0343 (12)	0.0256 (12)	0.0232 (12)	−0.0027 (9)	0.0146 (10)	−0.0038 (9)
C10	0.0374 (12)	0.0253 (12)	0.0319 (13)	−0.0004 (9)	0.0229 (11)	−0.0019 (9)
C12	0.0306 (12)	0.0320 (13)	0.0355 (14)	0.0085 (10)	0.0173 (11)	0.0045 (10)
C13	0.0340 (12)	0.0260 (12)	0.0375 (15)	0.0074 (10)	0.0130 (11)	0.0075 (10)
C14	0.0272 (11)	0.0349 (13)	0.0260 (12)	−0.0003 (9)	0.0084 (10)	0.0061 (10)
O21	0.0332 (8)	0.0376 (10)	0.0236 (9)	−0.0069 (7)	0.0123 (7)	0.0033 (7)
O22	0.0284 (8)	0.0299 (9)	0.0253 (9)	−0.0054 (6)	0.0092 (7)	−0.0015 (7)
O23	0.0326 (9)	0.0451 (11)	0.0289 (9)	−0.0069 (7)	0.0146 (7)	0.0029 (8)
C21	0.0247 (10)	0.0223 (11)	0.0219 (11)	0.0036 (8)	0.0115 (8)	0.0004 (8)
C22	0.0221 (10)	0.0268 (11)	0.0228 (11)	0.0001 (8)	0.0085 (9)	0.0007 (9)
C23	0.0219 (9)	0.0292 (11)	0.0277 (12)	0.0021 (9)	0.0117 (9)	0.0040 (9)
C24	0.0244 (10)	0.0264 (11)	0.0375 (13)	−0.0003 (9)	0.0146 (10)	−0.0002 (10)
C25	0.0268 (11)	0.0286 (12)	0.0333 (13)	−0.0015 (9)	0.0103 (10)	−0.0085 (10)
C26	0.0267 (11)	0.0293 (12)	0.0237 (11)	0.0037 (9)	0.0118 (9)	−0.0018 (9)
C27	0.0262 (10)	0.0226 (11)	0.0231 (11)	0.0008 (8)	0.0116 (9)	−0.0003 (9)
O31	0.0405 (10)	0.0423 (11)	0.0250 (9)	0.0110 (8)	0.0157 (8)	0.0049 (8)
O32	0.0409 (9)	0.0384 (10)	0.0227 (9)	0.0121 (8)	0.0165 (7)	0.0023 (7)
O33	0.0369 (9)	0.0446 (11)	0.0307 (10)	0.0119 (8)	0.0172 (8)	0.0082 (8)
C31	0.0230 (10)	0.0240 (11)	0.0251 (11)	−0.0023 (8)	0.0130 (9)	−0.0023 (9)
C32	0.0249 (10)	0.0255 (11)	0.0253 (11)	−0.0003 (8)	0.0131 (9)	−0.0006 (9)
C33	0.0272 (11)	0.0264 (11)	0.0287 (12)	−0.0018 (9)	0.0146 (10)	0.0032 (9)
C34	0.0272 (11)	0.0270 (12)	0.0340 (13)	−0.0005 (9)	0.0159 (10)	−0.0043 (9)
C35	0.0307 (12)	0.0358 (13)	0.0292 (13)	−0.0037 (10)	0.0168 (10)	−0.0102 (10)
C36	0.0264 (11)	0.0324 (12)	0.0227 (11)	−0.0008 (9)	0.0116 (9)	−0.0025 (9)
C37	0.0278 (10)	0.0250 (11)	0.0250 (12)	0.0000 (9)	0.0143 (9)	−0.0013 (9)
O1	0.0383 (10)	0.0427 (11)	0.0363 (10)	0.0041 (8)	0.0177 (8)	−0.0051 (8)
O2	0.0577 (12)	0.0356 (10)	0.0354 (10)	−0.0047 (8)	0.0271 (9)	−0.0056 (8)

Geometric parameters (Å, º)

N1—C2	1.487 (3)	C13—H13B	0.99
N1—C14	1.492 (3)	C14—H14A	0.99
N1—H1A	0.92	C14—H14B	0.99
N1—H1B	0.92	O21—C27	1.262 (3)
N4—C5	1.466 (3)	O22—C27	1.262 (3)
N4—C3	1.470 (3)	O23—C23	1.371 (3)
N4—H4	0.92	O23—H23	0.84
N8—C9	1.487 (3)	C21—C26	1.387 (3)
N8—C7	1.496 (3)	C21—C22	1.398 (3)
N8—H8A	0.92	C21—C27	1.506 (3)
N8—H8B	0.92	C22—C23	1.396 (3)
N11—C10	1.469 (3)	C22—H22A	0.95
N11—C12	1.477 (3)	C23—C24	1.390 (3)
N11—H11A	0.92	C24—C25	1.389 (4)
C2—C3	1.515 (4)	C24—H24	0.95
C2—H2A	0.99	C25—C26	1.398 (4)
C2—H2B	0.99	C25—H25	0.95
C3—H3A	0.99	C26—H26	0.95
C3—H3B	0.99	O31—C37	1.247 (3)
C5—C6	1.521 (4)	O32—C37	1.267 (3)
C5—H5A	0.99	O33—C33	1.365 (3)
C5—H5B	0.99	O33—H33	0.84
C6—C7	1.523 (4)	C31—C32	1.384 (3)
C6—H6A	0.99	C31—C36	1.400 (3)
C6—H6B	0.99	C31—C37	1.523 (3)
C7—H7A	0.99	C32—C33	1.404 (3)
C7—H7B	0.99	C32—H32	0.95
C9—C10	1.512 (3)	C33—C34	1.391 (4)
C9—H9A	0.99	C34—C35	1.390 (4)
C9—H9B	0.99	C34—H34	0.95
C10—H10A	0.99	C35—C36	1.395 (3)
C10—H10B	0.99	C35—H35	0.95
C12—C13	1.528 (4)	C36—H36	0.95
C12—H12A	0.99	O1—H11	0.84
C12—H12B	0.99	O1—H12	0.84
C13—C14	1.520 (4)	O2—H21	0.84
C13—H13A	0.99	O2—H22	0.84
C2—N1—C14	113.99 (19)	C13—C12—H12A	109.2
C2—N1—H1A	108.8	N11—C12—H12B	109.2
C14—N1—H1A	108.8	C13—C12—H12B	109.2
C2—N1—H1B	108.8	H12A—C12—H12B	107.9
C14—N1—H1B	108.8	C14—C13—C12	113.6 (2)
H1A—N1—H1B	107.6	C14—C13—H13A	108.9
C5—N4—C3	110.88 (19)	C12—C13—H13A	108.9
C5—N4—H4	109.5	C14—C13—H13B	108.9
C3—N4—H4	109.5	C12—C13—H13B	108.9
C9—N8—C7	114.02 (19)	H13A—C13—H13B	107.7
C9—N8—H8A	108.7	N1—C14—C13	110.2 (2)
C7—N8—H8A	108.7	N1—C14—H14A	109.6
C9—N8—H8B	108.7	C13—C14—H14A	109.6
C7—N8—H8B	108.7	N1—C14—H14B	109.6
H8A—N8—H8B	107.6	C13—C14—H14B	109.6
C10—N11—C12	110.87 (18)	H14A—C14—H14B	108.1
C10—N11—H11A	109.5	C23—O23—H23	109.5
C12—N11—H11A	109.5	C26—C21—C22	120.3 (2)
N1—C2—C3	109.57 (19)	C26—C21—C27	120.5 (2)
N1—C2—H2A	109.8	C22—C21—C27	119.1 (2)
C3—C2—H2A	109.8	C23—C22—C21	119.7 (2)
N1—C2—H2B	109.8	C23—C22—H22A	120.2
C3—C2—H2B	109.8	C21—C22—H22A	120.2
H2A—C2—H2B	108.2	O23—C23—C24	118.6 (2)
N4—C3—C2	111.3 (2)	O23—C23—C22	121.4 (2)
N4—C3—H3A	109.4	C24—C23—C22	120.0 (2)
C2—C3—H3A	109.4	C25—C24—C23	120.2 (2)
N4—C3—H3B	109.4	C25—C24—H24	119.9
C2—C3—H3B	109.4	C23—C24—H24	119.9
H3A—C3—H3B	108.0	C24—C25—C26	120.1 (2)
N4—C5—C6	112.3 (2)	C24—C25—H25	120.0
N4—C5—H5A	109.1	C26—C25—H25	120.0
C6—C5—H5A	109.1	C21—C26—C25	119.7 (2)
N4—C5—H5B	109.1	C21—C26—H26	120.1
C6—C5—H5B	109.1	C25—C26—H26	120.1
H5A—C5—H5B	107.9	O21—C27—O22	123.3 (2)
C5—C6—C7	113.9 (2)	O21—C27—C21	118.5 (2)
C5—C6—H6A	108.8	O22—C27—C21	118.2 (2)
C7—C6—H6A	108.8	C33—O33—H33	109.5
C5—C6—H6B	108.8	C32—C31—C36	120.2 (2)
C7—C6—H6B	108.8	C32—C31—C37	119.8 (2)
H6A—C6—H6B	107.7	C36—C31—C37	120.0 (2)
N8—C7—C6	110.9 (2)	C31—C32—C33	120.3 (2)
N8—C7—H7A	109.5	C31—C32—H32	119.8
C6—C7—H7A	109.5	C33—C32—H32	119.8
N8—C7—H7B	109.5	O33—C33—C34	123.9 (2)
C6—C7—H7B	109.5	O33—C33—C32	116.6 (2)
H7A—C7—H7B	108.1	C34—C33—C32	119.5 (2)
N8—C9—C10	110.07 (19)	C35—C34—C33	120.1 (2)
N8—C9—H9A	109.6	C35—C34—H34	119.9
C10—C9—H9A	109.6	C33—C34—H34	119.9
N8—C9—H9B	109.6	C34—C35—C36	120.6 (2)
C10—C9—H9B	109.6	C34—C35—H35	119.7
H9A—C9—H9B	108.2	C36—C35—H35	119.7
N11—C10—C9	110.5 (2)	C35—C36—C31	119.3 (2)
N11—C10—H10A	109.5	C35—C36—H36	120.3
C9—C10—H10A	109.5	C31—C36—H36	120.3
N11—C10—H10B	109.5	O31—C37—O32	123.8 (2)
C9—C10—H10B	109.5	O31—C37—C31	118.9 (2)
H10A—C10—H10B	108.1	O32—C37—C31	117.2 (2)
N11—C12—C13	111.95 (19)	H11—O1—H12	109.3
N11—C12—H12A	109.2	H21—O2—H22	109.6
C14—N1—C2—C3	−170.0 (2)	C22—C21—C26—C25	1.5 (3)
C5—N4—C3—C2	−174.1 (2)	C27—C21—C26—C25	−175.6 (2)
N1—C2—C3—N4	64.5 (3)	C24—C25—C26—C21	−1.2 (3)
C3—N4—C5—C6	179.2 (2)	C26—C21—C27—O21	−20.7 (3)
N4—C5—C6—C7	−64.6 (3)	C22—C21—C27—O21	162.2 (2)
C9—N8—C7—C6	−171.4 (2)	C26—C21—C27—O22	157.0 (2)
C5—C6—C7—N8	66.8 (3)	C22—C21—C27—O22	−20.2 (3)
C7—N8—C9—C10	166.9 (2)	C36—C31—C32—C33	−0.1 (3)
C12—N11—C10—C9	179.23 (19)	C37—C31—C32—C33	−178.7 (2)
N8—C9—C10—N11	−65.4 (3)	C31—C32—C33—O33	−176.2 (2)
C10—N11—C12—C13	−176.7 (2)	C31—C32—C33—C34	2.1 (3)
N11—C12—C13—C14	64.2 (3)	O33—C33—C34—C35	175.5 (2)
C2—N1—C14—C13	172.7 (2)	C32—C33—C34—C35	−2.7 (4)
C12—C13—C14—N1	−68.5 (3)	C33—C34—C35—C36	1.3 (4)
C26—C21—C22—C23	−0.4 (3)	C34—C35—C36—C31	0.8 (4)
C27—C21—C22—C23	176.75 (19)	C32—C31—C36—C35	−1.4 (3)
C21—C22—C23—O23	178.4 (2)	C37—C31—C36—C35	177.2 (2)
C21—C22—C23—C24	−1.0 (3)	C32—C31—C37—O31	−178.2 (2)
O23—C23—C24—C25	−178.2 (2)	C36—C31—C37—O31	3.2 (3)
C22—C23—C24—C25	1.2 (3)	C32—C31—C37—O32	5.1 (3)
C23—C24—C25—C26	−0.1 (3)	C36—C31—C37—O32	−173.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···O2	0.84	1.94	2.776 (3)	171
O1—H12···O22	0.84	1.92	2.754 (3)	176
O2—H21···O31^i	0.84	1.89	2.714 (3)	167
O2—H22···O32	0.84	2.02	2.835 (3)	163
O23—H23···O21^ii	0.84	1.84	2.674 (3)	171
O33—H33···O1^iii	0.84	1.83	2.660 (3)	168
N1—H1A···O21	0.92	1.82	2.729 (3)	169
N1—H1B···N11	0.92	2.10	2.839 (3)	137
N4—H4···O31	0.92	2.25	3.114 (3)	155
N8—H8A···N4	0.92	2.11	2.848 (3)	136
N8—H8B···O32^iv	0.92	1.85	2.767 (3)	177
N11—H11A···O22^v	0.92	2.20	3.035 (3)	150

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

(IV) Cyclam/5-hydroxyisophthalic acid/methanol (1/1/1)

Crystal data

C10H26N4·C8H4O5·CH4O	F(000) = 896
Mr = 414.50	Dx = 1.293 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4886 reflections
a = 9.7666 (3) Å	θ = 2.7–27.6°
b = 13.9931 (6) Å	µ = 0.10 mm^−1
c = 15.9476 (6) Å	T = 150 K
β = 102.280 (2)°	Block, colourless
V = 2129.61 (14) Å^3	0.20 × 0.16 × 0.16 mm
Z = 4

Data collection

Kappa-CCD diffractometer	3059 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.075
Graphite monochromator	θmax = 27.6°, θmin = 2.7°
ϕ scans, and ω scans with κ offsets	h = 0→12
16817 measured reflections	k = 0→18
4886 independent reflections	l = −20→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.193	w = 1/[σ^2(Fo^2) + (0.1053P)^2 + 0.1884P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4886 reflections	Δρmax = 0.47 e Å^−3
266 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (4)

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

	x	y	z	Uiso*/Ueq
N11	0.28613 (19)	0.59374 (14)	0.40901 (11)	0.0292 (5)
C12	0.3425 (2)	0.61409 (18)	0.33063 (14)	0.0320 (5)
C13	0.4722 (2)	0.55579 (19)	0.32817 (15)	0.0337 (5)
N14	0.57326 (19)	0.56396 (14)	0.40894 (12)	0.0308 (5)
C15	0.6978 (2)	0.50564 (18)	0.41352 (15)	0.0346 (6)
C16	0.8014 (2)	0.5236 (2)	0.49773 (17)	0.0389 (6)
C17	0.7420 (3)	0.50876 (17)	0.57711 (15)	0.0341 (6)
N21	−0.0456 (3)	0.48284 (16)	0.12437 (14)	0.0488 (6)
C22	0.0886 (4)	0.4343 (2)	0.15241 (19)	0.0611 (9)
C23	0.2054 (3)	0.4885 (2)	0.12855 (19)	0.0617 (10)
N24	0.2063 (2)	0.48064 (18)	0.03620 (16)	0.0501 (6)
C25	0.3113 (3)	0.5417 (3)	0.0107 (3)	0.0748 (12)
C26	0.3052 (4)	0.5350 (3)	−0.0829 (3)	0.0768 (12)
C27	0.1725 (5)	0.5744 (2)	−0.1364 (3)	0.0781 (13)
O1	−0.55216 (17)	0.78419 (13)	0.03018 (10)	0.0377 (4)
O2	−0.36115 (17)	0.71160 (13)	0.00513 (9)	0.0376 (4)
O3	0.01127 (17)	0.60616 (13)	0.25663 (10)	0.0392 (5)
O4	0.02053 (16)	0.68147 (13)	0.38008 (10)	0.0356 (4)
O5	−0.47451 (17)	0.81443 (12)	0.34667 (9)	0.0327 (4)
C1	−0.3712 (2)	0.74406 (15)	0.14980 (13)	0.0242 (5)
C2	−0.2388 (2)	0.70583 (16)	0.18104 (13)	0.0258 (5)
C3	−0.1841 (2)	0.70156 (15)	0.26955 (13)	0.0246 (5)
C4	−0.2631 (2)	0.73728 (15)	0.32608 (13)	0.0240 (5)
C5	−0.3951 (2)	0.77726 (16)	0.29466 (13)	0.0249 (5)
C6	−0.4491 (2)	0.77928 (16)	0.20676 (13)	0.0254 (5)
C7	−0.4340 (2)	0.74732 (17)	0.05428 (13)	0.0271 (5)
C8	−0.0408 (2)	0.66008 (16)	0.30436 (14)	0.0285 (5)
O6	0.0207 (2)	0.78983 (16)	0.52975 (13)	0.0588 (6)
C9	0.0994 (3)	0.7340 (2)	0.59708 (19)	0.0567 (8)
H11A	0.3492	0.6160	0.4562	0.035*
H11B	0.2041	0.6274	0.4053	0.035*
H12A	0.3655	0.6829	0.3293	0.038*
H12B	0.2693	0.5997	0.2789	0.038*
H13A	0.4459	0.4879	0.3172	0.040*
H13B	0.5148	0.5787	0.2808	0.040*
H14	0.5999	0.6269	0.4173	0.037*
H15A	0.7421	0.5214	0.3649	0.041*
H15B	0.6713	0.4372	0.4092	0.041*
H16A	0.8826	0.4805	0.5009	0.047*
H16B	0.8361	0.5901	0.4978	0.047*
H17A	0.8092	0.5337	0.6278	0.041*
H17B	0.6538	0.5454	0.5712	0.041*
H21A	−0.0567	0.4979	0.0672	0.059*
H21B	−0.0432	0.5393	0.1543	0.059*
H22A	0.0832	0.3700	0.1260	0.073*
H22B	0.1078	0.4260	0.2155	0.073*
H23A	0.1973	0.5567	0.1433	0.074*
H23B	0.2955	0.4643	0.1625	0.074*
H24	0.2234	0.4181	0.0237	0.060*
H25A	0.4057	0.5225	0.0425	0.090*
H25B	0.2955	0.6088	0.0259	0.090*
H26A	0.3143	0.4671	−0.0983	0.092*
H26B	0.3858	0.5702	−0.0964	0.092*
H27A	0.1782	0.5731	−0.1976	0.094*
H27B	0.1614	0.6418	−0.1201	0.094*
H5	−0.4324	0.8082	0.3981	0.049*
H2	−0.1852	0.6825	0.1422	0.031*
H4	−0.2268	0.7343	0.3862	0.029*
H6	−0.5399	0.8049	0.1853	0.030*
H6A	0.0092	0.7591	0.4835	0.088*
H9A	0.1948	0.7257	0.5880	0.085*
H9B	0.0549	0.6713	0.5979	0.085*
H9C	0.1028	0.7664	0.6520	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0236 (10)	0.0340 (11)	0.0266 (9)	0.0024 (8)	−0.0023 (8)	0.0016 (8)
C12	0.0295 (12)	0.0373 (13)	0.0262 (11)	−0.0012 (10)	−0.0007 (9)	0.0020 (10)
C13	0.0323 (13)	0.0396 (13)	0.0284 (12)	−0.0007 (11)	0.0045 (10)	0.0004 (10)
N14	0.0268 (10)	0.0330 (11)	0.0308 (10)	0.0016 (8)	0.0022 (8)	0.0027 (8)
C15	0.0296 (13)	0.0382 (13)	0.0379 (13)	0.0030 (10)	0.0118 (10)	0.0069 (10)
C16	0.0229 (12)	0.0436 (15)	0.0484 (15)	0.0026 (11)	0.0036 (11)	0.0105 (12)
C17	0.0293 (12)	0.0329 (13)	0.0360 (13)	0.0005 (10)	−0.0019 (10)	0.0019 (10)
N21	0.0758 (18)	0.0364 (12)	0.0352 (12)	0.0071 (12)	0.0141 (11)	−0.0004 (9)
C22	0.088 (3)	0.0510 (18)	0.0392 (16)	0.0278 (18)	0.0017 (16)	−0.0005 (13)
C23	0.059 (2)	0.061 (2)	0.0498 (17)	0.0290 (17)	−0.0231 (15)	−0.0259 (15)
N24	0.0374 (13)	0.0489 (15)	0.0592 (15)	0.0028 (11)	−0.0008 (11)	−0.0212 (12)
C25	0.0427 (18)	0.065 (2)	0.120 (3)	−0.0152 (17)	0.024 (2)	−0.043 (2)
C26	0.069 (2)	0.055 (2)	0.121 (3)	−0.0179 (19)	0.054 (3)	−0.014 (2)
C27	0.131 (4)	0.0406 (18)	0.081 (3)	−0.011 (2)	0.064 (3)	−0.0016 (16)
O1	0.0337 (10)	0.0547 (11)	0.0217 (8)	0.0090 (8)	−0.0006 (7)	0.0053 (7)
O2	0.0342 (9)	0.0607 (12)	0.0177 (7)	0.0052 (8)	0.0054 (7)	−0.0003 (7)
O3	0.0336 (9)	0.0500 (11)	0.0313 (9)	0.0126 (8)	0.0011 (7)	−0.0070 (8)
O4	0.0300 (9)	0.0471 (10)	0.0254 (8)	0.0085 (8)	−0.0036 (7)	−0.0013 (7)
O5	0.0328 (9)	0.0465 (10)	0.0186 (7)	0.0083 (8)	0.0053 (6)	0.0001 (7)
C1	0.0264 (12)	0.0262 (11)	0.0188 (10)	−0.0037 (9)	0.0023 (8)	0.0026 (8)
C2	0.0277 (11)	0.0296 (12)	0.0204 (10)	0.0001 (9)	0.0055 (9)	0.0005 (8)
C3	0.0250 (11)	0.0259 (11)	0.0217 (10)	−0.0015 (9)	0.0020 (9)	0.0018 (8)
C4	0.0246 (11)	0.0290 (11)	0.0169 (9)	−0.0022 (9)	0.0008 (8)	0.0008 (8)
C5	0.0253 (11)	0.0290 (12)	0.0206 (10)	0.0000 (9)	0.0053 (9)	−0.0005 (8)
C6	0.0230 (11)	0.0305 (12)	0.0214 (10)	0.0017 (9)	0.0017 (9)	0.0035 (8)
C7	0.0266 (12)	0.0340 (13)	0.0200 (10)	−0.0013 (10)	0.0031 (9)	0.0035 (9)
C8	0.0276 (12)	0.0328 (12)	0.0243 (11)	0.0012 (10)	0.0039 (9)	0.0026 (9)
O6	0.0631 (14)	0.0643 (14)	0.0450 (11)	0.0118 (12)	0.0029 (10)	−0.0050 (10)
C9	0.062 (2)	0.0567 (19)	0.0473 (17)	0.0056 (16)	0.0036 (15)	−0.0043 (14)

Geometric parameters (Å, º)

N11—C17^i	1.486 (3)	N24—H24	0.92
N11—C12	1.496 (3)	C25—C26	1.484 (5)
N11—H11A	0.92	C25—H25A	0.99
N11—H11B	0.92	C25—H25B	0.99
C12—C13	1.514 (3)	C26—C27	1.497 (6)
C12—H12A	0.99	C26—H26A	0.99
C12—H12B	0.99	C26—H26B	0.99
C13—N14	1.451 (3)	C27—N21^ii	1.522 (4)
C13—H13A	0.99	C27—H27A	0.99
C13—H13B	0.99	C27—H27B	0.99
N14—C15	1.454 (3)	O1—C7	1.248 (3)
N14—H14	0.92	O2—C7	1.268 (3)
C15—C16	1.521 (4)	O3—C8	1.254 (3)
C15—H15A	0.99	O4—C8	1.265 (3)
C15—H15B	0.99	O5—C5	1.354 (2)
C16—C17	1.514 (3)	O5—H5	0.84
C16—H16A	0.99	C1—C2	1.390 (3)
C16—H16B	0.99	C1—C6	1.393 (3)
C17—N11^i	1.486 (3)	C1—C7	1.517 (3)
C17—H17A	0.99	C2—C3	1.400 (3)
C17—H17B	0.99	C2—H2	0.95
N21—C22	1.460 (4)	C3—C4	1.398 (3)
N21—C27^ii	1.522 (4)	C3—C8	1.508 (3)
N21—H21A	0.92	C4—C5	1.397 (3)
N21—H21B	0.92	C4—H4	0.95
C22—C23	1.485 (5)	C5—C6	1.389 (3)
C22—H22A	0.99	C6—H6	0.95
C22—H22B	0.99	O6—C9	1.415 (4)
C23—N24	1.479 (4)	O6—H6A	0.84
C23—H23A	0.99	C9—H9A	0.98
C23—H23B	0.99	C9—H9B	0.98
N24—C25	1.457 (4)	C9—H9C	0.98
C17^i—N11—C12	114.89 (18)	C22—C23—H23B	109.1
C17^i—N11—H11A	108.5	H23A—C23—H23B	107.8
C12—N11—H11A	108.5	C25—N24—C23	112.8 (3)
C17^i—N11—H11B	108.5	C25—N24—H24	109.0
C12—N11—H11B	108.5	C23—N24—H24	109.0
H11A—N11—H11B	107.5	N24—C25—C26	111.3 (3)
N11—C12—C13	112.18 (18)	N24—C25—H25A	109.4
N11—C12—H12A	109.2	C26—C25—H25A	109.4
C13—C12—H12A	109.2	N24—C25—H25B	109.4
N11—C12—H12B	109.2	C26—C25—H25B	109.4
C13—C12—H12B	109.2	H25A—C25—H25B	108.0
H12A—C12—H12B	107.9	C25—C26—C27	113.2 (3)
N14—C13—C12	110.44 (19)	C25—C26—H26A	108.9
N14—C13—H13A	109.6	C27—C26—H26A	108.9
C12—C13—H13A	109.6	C25—C26—H26B	108.9
N14—C13—H13B	109.6	C27—C26—H26B	108.9
C12—C13—H13B	109.6	H26A—C26—H26B	107.7
H13A—C13—H13B	108.1	C26—C27—N21^ii	111.3 (3)
C13—N14—C15	113.84 (19)	C26—C27—H27A	109.4
C13—N14—H14	108.8	N21^ii—C27—H27A	109.4
C15—N14—H14	108.8	C26—C27—H27B	109.4
N14—C15—C16	110.1 (2)	N21^ii—C27—H27B	109.4
N14—C15—H15A	109.6	H27A—C27—H27B	108.0
C16—C15—H15A	109.6	C5—O5—H5	109.5
N14—C15—H15B	109.6	C2—C1—C6	119.86 (19)
C16—C15—H15B	109.6	C2—C1—C7	121.20 (19)
H15A—C15—H15B	108.2	C6—C1—C7	118.9 (2)
C17—C16—C15	114.5 (2)	C1—C2—C3	120.27 (19)
C17—C16—H16A	108.6	C1—C2—H2	119.9
C15—C16—H16A	108.6	C3—C2—H2	119.9
C17—C16—H16B	108.6	C4—C3—C2	119.4 (2)
C15—C16—H16B	108.6	C4—C3—C8	119.77 (18)
H16A—C16—H16B	107.6	C2—C3—C8	120.85 (18)
N11^i—C17—C16	111.9 (2)	C5—C4—C3	120.38 (18)
N11^i—C17—H17A	109.2	C5—C4—H4	119.8
C16—C17—H17A	109.2	C3—C4—H4	119.8
N11^i—C17—H17B	109.2	O5—C5—C6	117.82 (19)
C16—C17—H17B	109.2	O5—C5—C4	122.63 (18)
H17A—C17—H17B	107.9	C6—C5—C4	119.55 (18)
C22—N21—C27^ii	114.7 (3)	C5—C6—C1	120.6 (2)
C22—N21—H21A	108.6	C5—C6—H6	119.7
C27^ii—N21—H21A	108.6	C1—C6—H6	119.7
C22—N21—H21B	108.6	O1—C7—O2	125.2 (2)
C27^ii—N21—H21B	108.6	O1—C7—C1	118.14 (19)
H21A—N21—H21B	107.6	O2—C7—C1	116.7 (2)
N21—C22—C23	111.8 (3)	O3—C8—O4	123.4 (2)
N21—C22—H22A	109.2	O3—C8—C3	118.22 (19)
C23—C22—H22A	109.2	O4—C8—C3	118.34 (19)
N21—C22—H22B	109.2	C9—O6—H6A	109.5
C23—C22—H22B	109.2	O6—C9—H9A	109.5
H22A—C22—H22B	107.9	O6—C9—H9B	109.5
N24—C23—C22	112.6 (2)	H9A—C9—H9B	109.5
N24—C23—H23A	109.1	O6—C9—H9C	109.5
C22—C23—H23A	109.1	H9A—C9—H9C	109.5
N24—C23—H23B	109.1	H9B—C9—H9C	109.5
C17^i—N11—C12—C13	−54.1 (3)	C2—C3—C4—C5	−0.3 (3)
N11—C12—C13—N14	−50.1 (3)	C8—C3—C4—C5	179.00 (19)
C12—C13—N14—C15	176.73 (19)	C3—C4—C5—O5	−178.7 (2)
C13—N14—C15—C16	176.37 (19)	C3—C4—C5—C6	1.5 (3)
N14—C15—C16—C17	55.1 (3)	O5—C5—C6—C1	178.58 (19)
C15—C16—C17—N11^i	69.8 (3)	C4—C5—C6—C1	−1.7 (3)
C27^ii—N21—C22—C23	172.5 (3)	C2—C1—C6—C5	0.5 (3)
N21—C22—C23—N24	−75.2 (3)	C7—C1—C6—C5	179.8 (2)
C22—C23—N24—C25	173.9 (3)	C2—C1—C7—O1	−178.7 (2)
C23—N24—C25—C26	−177.6 (3)	C6—C1—C7—O1	2.0 (3)
N24—C25—C26—C27	66.3 (4)	C2—C1—C7—O2	1.6 (3)
C25—C26—C27—N21^ii	−63.9 (4)	C6—C1—C7—O2	−177.7 (2)
C6—C1—C2—C3	0.7 (3)	C4—C3—C8—O3	160.9 (2)
C7—C1—C2—C3	−178.6 (2)	C2—C3—C8—O3	−19.8 (3)
C1—C2—C3—C4	−0.9 (3)	C4—C3—C8—O4	−19.1 (3)
C1—C2—C3—C8	179.9 (2)	C2—C3—C8—O4	160.2 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2^iii	0.84	1.72	2.560 (2)	174
O6—H6A···O4	0.84	2.00	2.827 (3)	169
N11—H11A···O1^iv	0.92	1.95	2.801 (3)	154
N11—H11B···O4	0.92	1.91	2.818 (2)	169
N14—H14···O2^iv	0.92	2.64	3.494 (3)	154
N21—H21A···N24^ii	0.92	1.98	2.752 (3)	140
N21—H21B···O3	0.92	1.86	2.690 (3)	149
N24—H24···O2^ii	0.92	2.36	3.222 (3)	156

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