meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra­azacyclotetradecane as a building block in supramolecular chemistry; salts formed with 2,2′-biphenol, 4,4′-biphenol, 4,4′-thiodiphenol, 4,4′-sulfonyldiphenol, 3- and 4-hydroxybenzoic acids, 3,5-dihydroxybenzoic acid and phenylphosphonic acid; supramolecular structures in zero, one, two and three dimensions

The structure of meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetra­azacyclotetradecane–2,2′-biphenol (1/2), (C₁₆H₃₆N₄).(C₁₂H₁₀O₂)₂ (1), is a salt [C₁₆H₃₈N₄]²⁺.2[HOC₆H₄C₆H₄O]⁻: the cations are centrosymmetric with two protons held within the N₄ cavity of the macrocycle by N—H...N hydrogen bonds, and the phenolate anions contain intramolecular O—H...O⁻ hydrogen bonds. The ions are linked into a finite centrosymmetric aggregate by means of N—H...O hydrogen bonds. meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane–4,4′-thiobiphen­ol–methanol (1/2/2), (C₁₆H₃₆N₄).(C₁₂H₁₀O₂S)₂.(CH₄O)₂ (2), and meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane–4,4′-sulfonylbiphe­nol–methanol (1/2/2), (C₁₆H₃₆N₄).(C₁₂H₁₀O₄S)₂.(CH₄O)₂ (3), are isomorphous: each is a salt, [C₁₆H₃₈N₄]²⁺.2[HOC₆H₄SC₆H₄O]⁻.2MeOH (2) and [C₁₆H₃₈N₄]²⁺.2[HOC₆H₄SO₂C₆H₄O]⁻.2MeOH (3), and in each the phenolate anions are linked by O—H...O⁻ hydrogen bonds into chains; antiparallel pairs of chains are cross-linked by the cations to form molecular ladders, with neutral methanol molecules acting as spacer units. In meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane–3-hydroxybenzoic acid–methanol (1/2/2) (4), 3-hydroxybenzoate anions form chains, again cross-linked in pairs by the [C₁₆H₃₈N₄]²⁺ cations to form molecular ladders, different from those in (2) and (3) in that the neutral methanol units are pendent from the ladders, rather than forming a part of it. meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane–4-hydroxybenzoic acid–methanol (1/2/1) (5) is again a salt, [C₁₆H₃₈N₄]²⁺.2[HOC₆H₄COO]⁻.MeOH: chains of 4-hydroxybenzoate anions are continuously cross-linked by two different types of [C₁₆H₃₈N₄]²⁺ cation into a two-dimensional net. Only one of the two types of cation is linked to the chains via neutral methanol spacer units. meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane–phenylphosphonic acid–water (1/4/2) (6) is a salt, [C₁₆H₄₀N₄]⁴⁺.4[C₆H₅PO₃H]⁻.2H₂O, containing the centrosymmetric tetra-protonated amine units, which have a conformation quite different from the trans-III conformation uniformly found in the [C₁₆H₃₈N₄]²⁺ cations. The phenylphosphonate anions and the water molecules are linked into chains of fused rings, which are linked by the cations into two-dimensional nets. In meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane–3,5-dihydroxybenzoic acid (1/2) (7), the 3,5-di­hydroxybenzoate anions in the unsolvated salt [C₁₆H₃₈N₄]²⁺.2[(HO)₂C₆H₃COO]⁻ are linked into continuous two-dimensional nets, which are in turn linked by the centrosymmetric cations to form a three-dimensional framework. meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane–4,4′-biphenol (1/3) (8) is a salt containing both neutral and anionic biphenol units, [C₁₆H₃₈N₄]²⁺.2[HOC₆H₄C₆H₄O]⁻.[HOC₆H₄C₆H₄OH]. The two types of biphenol unit form two-dimensional nets and these nets are linked by the cations to form three independent, three-dimensional frameworks which are fully interwoven, but not bonded to one another.

Computing details

Data collection: CAD-4-PC Software (Enraf-Nonius, 1992) for (1), (3), (4), (7), (8); MSC/AFC Diffractometer Control (Molecular Structure Corporation 1988) for (2); KappaCCD (Nonius, 1998) for (5), (6). Cell refinement: SET4 & CELDIM in CAD-4-PC Software (Enraf-Nonius, 1992) for (1), (3), (4), (7), (8); MSC/AFC Diffractometer Control (Molecular Structure Corporation 1988) for (2); DENZO (Nonius, 1998) for (5), (6). Data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989) for (1), (2), (3), (4), (7), (8); DENZO (Nonius, 1998) for (5), (6). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).

(1) Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane- 2,2'-biphenol (1/2)

Crystal data

C16H38N4^2+·2(C12H9O2^−)	F(000) = 356
Mr = 656.89	? #Insert any comments here.
Triclinic, P1	Dx = 1.199 Mg m^−3
a = 8.6323 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.943 (3) Å	Cell parameters from 25 reflections
c = 12.582 (2) Å	θ = 7.9–18.6°
α = 98.783 (17)°	µ = 0.08 mm^−1
β = 102.785 (15)°	T = 294 K
γ = 115.746 (11)°	Needle, colourless
V = 909.8 (4) Å^3	0.39 × 0.19 × 0.17 mm
Z = 1

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: X-ray tube	θmax = 25.5°, θmin = 2.4°
Graphite monochromator	h = −10→9
θ/2θ scans	k = 0→12
3375 measured reflections	l = −15→15
3375 independent reflections	3 standard reflections every 120 min
2146 reflections with I > 2σ(I)	intensity decay: no decay, variation .2%

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0684P)^2 + 0.0289P] where P = (Fo^2 + 2Fc^2)/3
3375 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 7.1857 (0.0045) x + 1.8968 (0.0086) y + 9.1043 (0.0078) z = 2.3388 (0.0024)

* -0.0112 (0.0014) C11 * 0.0157 (0.0014) C12 * -0.0073 (0.0015) C13 * -0.0060 (0.0017) C14 * 0.0105 (0.0017) C15 * -0.0017 (0.0016) C16 0.0566 (0.0027) O1 - 0.0943 (0.0031) C21 0.6055 (0.0037) C22 0.5166 (0.0048) C23 - 0.2727 (0.0055) C24 - 0.9960 (0.0051) C25 - 0.9025 (0.0041) C26 1.4083 (0.0035) O2

Rms deviation of fitted atoms = 0.0098

- 7.3580 (0.0047) x - 0.9579 (0.0091) y + 3.3320 (0.0117) z = 0.9877 (0.0031)

Angle to previous plane (with approximate e.s.d.) = 39.6 (1)

* 0.0103 (0.0015) C21 * -0.0092 (0.0014) C22 * -0.0004 (0.0016) C23 * 0.0090 (0.0018) C24 * -0.0076 (0.0018) C25 * -0.0021 (0.0017) C26 - 0.0157 (0.0030) O2 0.0686 (0.0033) C11 - 0.6685 (0.0039) C12 - 0.6244 (0.0052) C13 0.1451 (0.0057) C14 0.8972 (0.0053) C15 0.8449 (0.0042) C16 - 1.3971 (0.0036) O1

Rms deviation of fitted atoms = 0.0075

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

	x	y	z	Uiso*/Ueq
O1	0.14207 (18)	0.37187 (15)	0.29777 (11)	0.0556 (4)
O2	0.0255 (2)	0.16877 (17)	0.39653 (12)	0.0624 (4)
C11	−0.0941 (3)	0.1455 (2)	0.15110 (16)	0.0475 (5)
C12	0.0069 (3)	0.3086 (2)	0.19977 (16)	0.0468 (5)
C13	−0.0374 (3)	0.4035 (3)	0.14253 (18)	0.0586 (6)
C14	−0.1790 (3)	0.3434 (3)	0.0434 (2)	0.0680 (6)
C15	−0.2817 (3)	0.1857 (3)	−0.00297 (19)	0.0730 (7)
C16	−0.2378 (3)	0.0891 (3)	0.05043 (18)	0.0655 (6)
C21	−0.0495 (3)	0.0348 (2)	0.20023 (17)	0.0501 (5)
C22	0.0041 (3)	0.0482 (2)	0.31663 (18)	0.0510 (5)
C23	0.0350 (3)	−0.0651 (3)	0.3548 (2)	0.0617 (6)
C24	0.0159 (3)	−0.1912 (3)	0.2793 (3)	0.0754 (7)
C25	−0.0316 (4)	−0.2053 (3)	0.1653 (3)	0.0825 (8)
C26	−0.0644 (3)	−0.0942 (2)	0.1266 (2)	0.0712 (7)
N1	0.4893 (2)	0.53683 (19)	0.34399 (12)	0.0486 (4)
C2	0.5633 (3)	0.7076 (2)	0.38016 (18)	0.0643 (6)
C3	0.4745 (3)	0.7500 (3)	0.45983 (18)	0.0630 (6)
N4	0.5138 (2)	0.70499 (18)	0.56377 (13)	0.0489 (4)
C5	0.4190 (3)	0.7275 (2)	0.64475 (17)	0.0524 (5)
C51	0.2156 (3)	0.6176 (3)	0.58954 (19)	0.0642 (6)
C52	0.4538 (4)	0.8961 (3)	0.6791 (2)	0.0860 (8)
C6	0.4952 (3)	0.6904 (3)	0.75197 (17)	0.0619 (6)
C7	0.4456 (3)	0.5223 (3)	0.74363 (16)	0.0606 (6)
C71	0.5275 (4)	0.5047 (4)	0.85817 (19)	0.0989 (10)
H2	0.0636	0.2479	0.3757	0.094*
H13	0.0318	0.5110	0.1728	0.070*
H14	−0.2054	0.4097	0.0076	0.082*
H15	−0.3797	0.1438	−0.0695	0.088*
H16	−0.3073	−0.0179	0.0177	0.079*
H23	0.0689	−0.0554	0.4323	0.074*
H24	0.0353	−0.2669	0.3057	0.091*
H25	−0.0418	−0.2892	0.1141	0.099*
H26	−0.0974	−0.1055	0.0489	0.085*
H1A	0.3673	0.4914	0.3164	0.058*
H1E	0.5175	0.5061	0.4058	0.058*
H2A	0.5419	0.7440	0.3140	0.077*
H2B	0.6934	0.7581	0.4179	0.077*
H3A	0.5186	0.8613	0.4790	0.076*
H3B	0.3441	0.6977	0.4225	0.076*
H4A	0.6343	0.7601	0.6001	0.059*
H51A	0.1671	0.6555	0.5324	0.096*
H51B	0.1565	0.6123	0.6463	0.096*
H51C	0.1951	0.5156	0.5552	0.096*
H52A	0.5823	0.9661	0.7105	0.129*
H52B	0.3968	0.9069	0.7348	0.129*
H52C	0.4041	0.9205	0.6133	0.129*
H6A	0.6267	0.7513	0.7765	0.074*
H6B	0.4555	0.7262	0.8114	0.074*
H7	0.3130	0.4597	0.7203	0.073*
H71A	0.4878	0.3965	0.8517	0.148*
H71B	0.4885	0.5457	0.9146	0.148*
H71C	0.6577	0.5609	0.8800	0.148*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0492 (8)	0.0496 (8)	0.0527 (9)	0.0164 (7)	0.0093 (7)	0.0079 (7)
O2	0.0810 (11)	0.0666 (10)	0.0502 (8)	0.0423 (9)	0.0253 (8)	0.0182 (7)
C11	0.0463 (11)	0.0481 (11)	0.0441 (11)	0.0187 (9)	0.0189 (9)	0.0094 (9)
C12	0.0455 (12)	0.0495 (11)	0.0474 (11)	0.0233 (10)	0.0189 (10)	0.0128 (9)
C13	0.0655 (15)	0.0545 (13)	0.0614 (14)	0.0323 (12)	0.0239 (12)	0.0167 (11)
C14	0.0755 (17)	0.0828 (18)	0.0601 (14)	0.0471 (15)	0.0227 (13)	0.0303 (13)
C15	0.0668 (16)	0.0893 (19)	0.0503 (14)	0.0341 (15)	0.0062 (12)	0.0175 (13)
C16	0.0651 (15)	0.0580 (13)	0.0512 (13)	0.0177 (12)	0.0124 (11)	0.0041 (11)
C21	0.0513 (12)	0.0426 (11)	0.0538 (12)	0.0180 (10)	0.0236 (10)	0.0124 (9)
C22	0.0484 (12)	0.0484 (12)	0.0604 (13)	0.0223 (10)	0.0264 (10)	0.0172 (10)
C23	0.0602 (14)	0.0617 (14)	0.0735 (15)	0.0303 (12)	0.0313 (12)	0.0301 (12)
C24	0.0838 (18)	0.0582 (15)	0.105 (2)	0.0389 (14)	0.0474 (16)	0.0389 (14)
C25	0.110 (2)	0.0485 (14)	0.096 (2)	0.0396 (15)	0.0471 (17)	0.0167 (13)
C26	0.0951 (19)	0.0480 (13)	0.0668 (15)	0.0284 (13)	0.0350 (14)	0.0133 (11)
N1	0.0471 (10)	0.0648 (11)	0.0354 (8)	0.0252 (9)	0.0163 (7)	0.0203 (8)
C2	0.0734 (16)	0.0605 (14)	0.0560 (13)	0.0235 (12)	0.0266 (12)	0.0281 (11)
C3	0.0800 (16)	0.0553 (13)	0.0607 (14)	0.0366 (12)	0.0223 (12)	0.0242 (11)
N4	0.0424 (9)	0.0566 (10)	0.0428 (9)	0.0215 (8)	0.0123 (7)	0.0107 (8)
C5	0.0463 (12)	0.0545 (12)	0.0505 (12)	0.0235 (10)	0.0150 (9)	0.0032 (9)
C51	0.0498 (14)	0.0736 (15)	0.0691 (15)	0.0314 (12)	0.0193 (11)	0.0156 (12)
C52	0.093 (2)	0.0620 (15)	0.0955 (19)	0.0339 (15)	0.0390 (16)	0.0002 (14)
C6	0.0541 (13)	0.0799 (16)	0.0435 (12)	0.0294 (12)	0.0190 (10)	0.0009 (11)
C7	0.0574 (13)	0.0921 (17)	0.0412 (11)	0.0371 (13)	0.0259 (10)	0.0253 (11)
C71	0.122 (2)	0.163 (3)	0.0433 (14)	0.086 (2)	0.0367 (15)	0.0451 (16)

Geometric parameters (Å, º)

O1—C12	1.329 (2)	C24—C25	1.369 (4)
O2—C22	1.357 (2)	C25—C26	1.383 (3)
C11—C16	1.394 (3)	N1—C2	1.480 (3)
C11—C12	1.414 (3)	N1—C7^i	1.497 (2)
C11—C21	1.487 (3)	C2—C3	1.504 (3)
C12—C13	1.398 (3)	C3—N4	1.463 (2)
C13—C14	1.368 (3)	N4—C5	1.488 (2)
C14—C15	1.367 (3)	C5—C51	1.523 (3)
C15—C16	1.384 (3)	C5—C6	1.536 (3)
C21—C26	1.400 (3)	C5—C52	1.540 (3)
C21—C22	1.401 (3)	C6—C7	1.514 (3)
C22—C23	1.393 (3)	C7—N1^i	1.497 (2)
C23—C24	1.374 (3)	C7—C71	1.530 (3)
C16—C11—C12	117.2 (2)	C25—C24—C23	119.9 (2)
C16—C11—C21	119.67 (19)	C24—C25—C26	119.7 (2)
C12—C11—C21	123.08 (18)	C25—C26—C21	122.3 (2)
O1—C12—C13	120.12 (18)	C2—N1—C7^i	115.86 (16)
O1—C12—C11	121.16 (18)	N1—C2—C3	110.43 (17)
C13—C12—C11	118.72 (18)	N4—C3—C2	110.83 (18)
C14—C13—C12	122.1 (2)	C3—N4—C5	115.82 (16)
C13—C14—C15	119.9 (2)	N4—C5—C51	108.78 (16)
C14—C15—C16	119.2 (2)	N4—C5—C6	106.95 (16)
C15—C16—C11	122.8 (2)	C51—C5—C6	111.20 (18)
C26—C21—C22	116.7 (2)	N4—C5—C52	112.33 (18)
C26—C21—C11	118.81 (19)	C51—C5—C52	109.28 (19)
C22—C21—C11	124.53 (18)	C6—C5—C52	108.31 (18)
O2—C22—C23	117.1 (2)	C7—C6—C5	117.79 (17)
O2—C22—C21	122.25 (19)	N1^i—C7—C6	109.98 (16)
C23—C22—C21	120.6 (2)	N1^i—C7—C71	109.72 (19)
C24—C23—C22	120.7 (2)	C6—C7—C71	111.2 (2)
C16—C11—C12—O1	177.59 (18)	O2—C22—C23—C24	179.9 (2)
C21—C11—C12—O1	−4.5 (3)	C21—C22—C23—C24	0.9 (3)
C16—C11—C12—C13	−2.7 (3)	C22—C23—C24—C25	0.8 (4)
C21—C11—C12—C13	175.21 (18)	C23—C24—C25—C26	−1.5 (4)
O1—C12—C13—C14	−177.85 (19)	C24—C25—C26—C21	0.5 (4)
C11—C12—C13—C14	2.4 (3)	C22—C21—C26—C25	1.2 (3)
C12—C13—C14—C15	−0.4 (4)	C11—C21—C26—C25	−177.7 (2)
C13—C14—C15—C16	−1.3 (4)	C7^i—N1—C2—C3	174.80 (17)
C14—C15—C16—C11	0.9 (4)	N1—C2—C3—N4	62.7 (2)
C12—C11—C16—C15	1.1 (3)	C2—C3—N4—C5	−174.49 (17)
C21—C11—C16—C15	−176.9 (2)	C3—N4—C5—C51	65.9 (2)
C16—C11—C21—C26	37.6 (3)	C3—N4—C5—C6	−173.95 (16)
C12—C11—C21—C26	−140.2 (2)	C3—N4—C5—C52	−55.2 (2)
C16—C11—C21—C22	−141.2 (2)	N4—C5—C6—C7	−70.1 (2)
C12—C11—C21—C22	41.0 (3)	C51—C5—C6—C7	48.5 (2)
C26—C21—C22—O2	179.21 (19)	C52—C5—C6—C7	168.59 (19)
C11—C21—C22—O2	−2.0 (3)	C5—C6—C7—N1^i	59.9 (2)
C26—C21—C22—C23	−1.9 (3)	C5—C6—C7—C71	−178.34 (18)
C11—C21—C22—C23	176.93 (19)

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
N1—H1A···O1	0.90	1.72	2.584 (3)	160
N1—H1E···N4^i	0.90	2.10	2.818 (3)	136
O2—H2···O1	0.82	1.70	2.488 (2)	162

Symmetry code: (i) −x+1, −y+1, −z+1.

(2) Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane- 4,4'-thiobiphenol-methanol (1/2/2)

Crystal data

C16H38N4^2+·2(C12H9O2S^−)·2(CH4O)	? #Insert any comments here.
Mr = 785.11	Dx = 1.202 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.659 (5) Å	Cell parameters from 7 reflections
b = 17.892 (5) Å	θ = 7.3–11.7°
c = 11.679 (5) Å	µ = 0.17 mm^−1
β = 103.107 (5)°	T = 294 K
V = 2169.3 (15) Å^3	Plate, colourless
Z = 2	0.45 × 0.40 × 0.35 mm
F(000) = 848

Data collection

Rigaku AFC7S diffractometer	Rint = 0.005
Radiation source: X-ray tube	θmax = 25.0°, θmin = 2.6°
Graphite monochromator	h = 0→12
θ/2θ scans	k = −3→21
3947 measured reflections	l = −13→13
3802 independent reflections	3 standard reflections every 120 min
2602 reflections with I > 2σ(I)	intensity decay: no decay, variation 1.3%

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)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0386P)^2 + 0.5476P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3802 reflections	Δρmax = 0.18 e Å^−3
250 parameters	Δρmin = −0.16 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: 0.0079 (8)

Special details

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

2.2021 (0.0115) x + 6.9120 (0.0250) y + 9.6780 (0.0097) z = 9.7313 (0.0203)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

- 6.3950 (0.0077) x + 14.1678 (0.0115) y + 0.2916 (0.0102) z = 12.0716 (0.0103)

Angle to previous plane (with approximate e.s.d.) = 85.4 (1)

* -0.0030 (0.0015) C11 * 0.0012 (0.0016) C12 * 0.0025 (0.0016) C13 * -0.0044 (0.0014) C14 * 0.0026 (0.0014) C15 * 0.0010 (0.0014) C16 - 0.0157 (0.0028) S1 0.0036 (0.0029) O14

Rms deviation of fitted atoms = 0.0027

2.2021 (0.0115) x + 6.9120 (0.0250) y + 9.6780 (0.0097) z = 9.7313 (0.0203)

Angle to previous plane (with approximate e.s.d.) = 85.4 (1)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

6.5928 (0.0071) x + 11.1414 (0.0120) y - 7.0894 (0.0084) z = 8.4897 (0.0106)

Angle to previous plane (with approximate e.s.d.) = 86.4 (1)

* 0.0014 (0.0014) C21 * -0.0076 (0.0013) C22 * 0.0068 (0.0013) C23 * 0.0001 (0.0013) C24 * -0.0062 (0.0014) C25 * 0.0055 (0.0015) C26 - 0.0041 (0.0026) S1 - 0.0283 (0.0026) O24

Rms deviation of fitted atoms = 0.0054

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.12477 (6)	0.90037 (3)	0.33408 (6)	0.0688 (2)
O14	−0.24497 (14)	0.73052 (9)	0.54380 (13)	0.0622 (4)
O24	0.55531 (14)	0.68254 (8)	0.39553 (13)	0.0563 (4)
C11	0.01274 (18)	0.84943 (12)	0.39596 (19)	0.0508 (5)
C12	0.0198 (2)	0.85044 (13)	0.5154 (2)	0.0615 (6)
C13	−0.0662 (2)	0.81075 (13)	0.56357 (19)	0.0605 (6)
C14	−0.16215 (18)	0.76840 (11)	0.49264 (18)	0.0478 (5)
C15	−0.17021 (19)	0.76773 (11)	0.37249 (18)	0.0511 (5)
C16	−0.08357 (19)	0.80770 (12)	0.32518 (18)	0.0500 (5)
C21	0.25397 (19)	0.83529 (12)	0.35116 (18)	0.0497 (5)
C22	0.2565 (2)	0.78005 (12)	0.26799 (18)	0.0530 (6)
C23	0.3571 (2)	0.73005 (12)	0.28090 (17)	0.0500 (5)
C24	0.45981 (19)	0.73180 (11)	0.38014 (18)	0.0452 (5)
C25	0.4554 (2)	0.78700 (12)	0.46368 (18)	0.0516 (5)
C26	0.3553 (2)	0.83788 (12)	0.44890 (19)	0.0541 (5)
N1	0.44606 (14)	0.46172 (8)	0.32989 (13)	0.0405 (4)
C2	0.5232 (2)	0.39167 (11)	0.35142 (18)	0.0519 (5)
C3	0.65844 (19)	0.40705 (12)	0.41881 (18)	0.0538 (5)
N4	0.65965 (14)	0.43751 (8)	0.53556 (13)	0.0404 (4)
C5	0.78775 (17)	0.46309 (11)	0.60467 (17)	0.0453 (5)
C51	0.8915 (2)	0.40230 (13)	0.6151 (2)	0.0670 (7)
C52	0.8286 (2)	0.53278 (13)	0.54649 (19)	0.0597 (6)
C6	0.77066 (18)	0.48131 (12)	0.72884 (17)	0.0485 (5)
C7	0.68709 (18)	0.54758 (11)	0.74550 (16)	0.0452 (5)
C71	0.6799 (2)	0.55608 (14)	0.87367 (17)	0.0630 (6)
O1	0.56065 (16)	0.57851 (9)	0.24233 (15)	0.0684 (5)
C1	0.6700 (3)	0.57961 (15)	0.1946 (2)	0.0768 (7)
H14	−0.3061	0.7156	0.4930	0.093*
H12	0.0837	0.8784	0.5642	0.074*
H13	−0.0598	0.8123	0.6443	0.073*
H15	−0.2346	0.7401	0.3234	0.061*
H16	−0.0900	0.8066	0.2444	0.060*
H22	0.1888	0.7768	0.2021	0.064*
H23	0.3568	0.6945	0.2228	0.060*
H25	0.5215	0.7896	0.5310	0.062*
H26	0.3562	0.8744	0.5057	0.065*
H1A	0.4888	0.4951	0.2954	0.049*
H1E	0.4398	0.4808	0.3996	0.049*
H2A	0.5255	0.3686	0.2768	0.062*
H2B	0.4824	0.3569	0.3954	0.062*
H3A	0.7079	0.3611	0.4271	0.065*
H3B	0.6988	0.4424	0.3754	0.065*
H4A	0.6296	0.4023	0.5774	0.048*
H51A	0.8638	0.3581	0.6489	0.101*
H51B	0.9705	0.4199	0.6645	0.101*
H51C	0.9049	0.3909	0.5385	0.101*
H52A	0.8533	0.5188	0.4753	0.090*
H52B	0.9004	0.5560	0.5992	0.090*
H52C	0.7580	0.5673	0.5285	0.090*
H6A	0.7354	0.4373	0.7584	0.058*
H6B	0.8557	0.4894	0.7786	0.058*
H7	0.7250	0.5931	0.7211	0.054*
H71A	0.6304	0.5997	0.8821	0.094*
H71B	0.7653	0.5611	0.9219	0.094*
H71C	0.6394	0.5127	0.8978	0.094*
H1	0.5662	0.6119	0.2914	0.103*
H1C	0.6633	0.5407	0.1368	0.115*	0.50
H1D	0.7456	0.5716	0.2560	0.115*	0.50
H1F	0.6760	0.6272	0.1582	0.115*	0.50
H1G	0.7266	0.6190	0.2305	0.115*	0.50
H1H	0.6444	0.5881	0.1114	0.115*	0.50
H1I	0.7139	0.5325	0.2091	0.115*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0514 (3)	0.0586 (4)	0.0958 (5)	0.0039 (3)	0.0152 (3)	0.0266 (3)
O14	0.0525 (9)	0.0726 (11)	0.0595 (10)	−0.0044 (8)	0.0082 (7)	0.0114 (8)
O24	0.0524 (8)	0.0484 (8)	0.0699 (10)	−0.0014 (7)	0.0181 (7)	−0.0075 (7)
C11	0.0391 (11)	0.0479 (12)	0.0623 (14)	0.0042 (9)	0.0052 (9)	0.0056 (10)
C12	0.0510 (13)	0.0663 (15)	0.0587 (15)	−0.0096 (11)	−0.0055 (11)	−0.0019 (12)
C13	0.0553 (13)	0.0748 (16)	0.0450 (13)	−0.0028 (12)	−0.0019 (10)	0.0012 (11)
C14	0.0407 (11)	0.0480 (12)	0.0527 (13)	0.0085 (9)	0.0061 (9)	0.0062 (10)
C15	0.0468 (12)	0.0491 (12)	0.0533 (13)	−0.0029 (10)	0.0030 (10)	−0.0074 (10)
C16	0.0493 (12)	0.0534 (12)	0.0473 (12)	0.0062 (10)	0.0108 (10)	−0.0017 (10)
C21	0.0428 (11)	0.0493 (12)	0.0575 (13)	−0.0055 (9)	0.0124 (10)	0.0104 (10)
C22	0.0477 (12)	0.0586 (14)	0.0497 (13)	−0.0176 (11)	0.0049 (10)	0.0115 (11)
C23	0.0563 (13)	0.0487 (12)	0.0469 (12)	−0.0168 (10)	0.0155 (10)	−0.0046 (10)
C24	0.0458 (11)	0.0414 (11)	0.0513 (12)	−0.0110 (9)	0.0170 (9)	0.0010 (9)
C25	0.0489 (12)	0.0522 (13)	0.0498 (12)	−0.0022 (10)	0.0029 (9)	−0.0056 (10)
C26	0.0542 (13)	0.0514 (13)	0.0565 (13)	−0.0016 (10)	0.0120 (10)	−0.0077 (10)
N1	0.0445 (9)	0.0407 (9)	0.0374 (8)	−0.0044 (7)	0.0118 (7)	−0.0065 (7)
C2	0.0646 (13)	0.0431 (12)	0.0469 (12)	0.0056 (10)	0.0101 (10)	−0.0109 (9)
C3	0.0535 (12)	0.0599 (14)	0.0491 (12)	0.0138 (11)	0.0136 (10)	−0.0089 (10)
N4	0.0425 (9)	0.0402 (9)	0.0405 (9)	−0.0008 (7)	0.0139 (7)	−0.0015 (7)
C5	0.0376 (10)	0.0485 (12)	0.0502 (12)	0.0002 (9)	0.0109 (9)	0.0071 (10)
C51	0.0481 (12)	0.0763 (17)	0.0767 (16)	0.0154 (12)	0.0142 (11)	0.0099 (13)
C52	0.0573 (13)	0.0626 (14)	0.0625 (14)	−0.0121 (11)	0.0207 (11)	0.0062 (11)
C6	0.0412 (11)	0.0560 (13)	0.0442 (12)	−0.0062 (9)	0.0007 (9)	0.0073 (10)
C7	0.0459 (11)	0.0483 (12)	0.0394 (11)	−0.0117 (9)	0.0054 (9)	−0.0044 (9)
C71	0.0716 (15)	0.0703 (15)	0.0433 (12)	−0.0129 (13)	0.0054 (11)	−0.0113 (11)
O1	0.0786 (11)	0.0532 (10)	0.0833 (12)	−0.0147 (8)	0.0393 (9)	−0.0145 (8)
C1	0.0883 (19)	0.0754 (17)	0.0778 (18)	0.0093 (15)	0.0420 (15)	0.0088 (14)

Geometric parameters (Å, º)

S1—C21	1.780 (2)	C24—C25	1.397 (3)
S1—C11	1.781 (2)	C25—C26	1.383 (3)
O14—C14	1.355 (2)	N1—C2	1.489 (2)
O24—C24	1.328 (2)	N1—C7^i	1.500 (2)
C11—C12	1.380 (3)	C2—C3	1.503 (3)
C11—C16	1.382 (3)	C3—N4	1.466 (2)
C12—C13	1.376 (3)	N4—C5	1.492 (2)
C13—C14	1.386 (3)	C5—C52	1.530 (3)
C14—C15	1.386 (3)	C5—C51	1.536 (3)
C15—C16	1.379 (3)	C5—C6	1.537 (3)
C21—C26	1.383 (3)	C6—C7	1.522 (3)
C21—C22	1.390 (3)	C7—N1^i	1.500 (2)
C22—C23	1.378 (3)	C7—C71	1.524 (3)
C23—C24	1.403 (3)	O1—C1	1.402 (3)
C21—S1—C11	101.11 (10)	C25—C24—C23	116.71 (19)
C12—C11—C16	118.3 (2)	C26—C25—C24	121.7 (2)
C12—C11—S1	121.06 (17)	C21—C26—C25	121.1 (2)
C16—C11—S1	120.62 (17)	C2—N1—C7^i	114.75 (15)
C13—C12—C11	121.2 (2)	N1—C2—C3	111.21 (16)
C12—C13—C14	120.5 (2)	N4—C3—C2	111.12 (16)
O14—C14—C15	123.03 (19)	C3—N4—C5	115.55 (15)
O14—C14—C13	118.4 (2)	N4—C5—C52	109.13 (16)
C15—C14—C13	118.5 (2)	N4—C5—C51	112.32 (17)
C16—C15—C14	120.52 (19)	C52—C5—C51	109.88 (17)
C15—C16—C11	121.0 (2)	N4—C5—C6	106.61 (14)
C26—C21—C22	117.7 (2)	C52—C5—C6	110.66 (17)
C26—C21—S1	120.69 (17)	C51—C5—C6	108.20 (17)
C22—C21—S1	121.60 (16)	C7—C6—C5	118.94 (16)
C23—C22—C21	121.5 (2)	N1^i—C7—C6	109.98 (15)
C22—C23—C24	121.2 (2)	N1^i—C7—C71	109.62 (16)
O24—C24—C25	121.41 (18)	C6—C7—C71	111.40 (17)
O24—C24—C23	121.87 (18)
C21—S1—C11—C12	85.4 (2)	C22—C23—C24—C25	−0.7 (3)
C21—S1—C11—C16	−94.51 (18)	O24—C24—C25—C26	−179.14 (19)
C16—C11—C12—C13	0.3 (3)	C23—C24—C25—C26	−0.6 (3)
S1—C11—C12—C13	−179.59 (18)	C22—C21—C26—C25	−0.3 (3)
C11—C12—C13—C14	0.2 (4)	S1—C21—C26—C25	179.22 (16)
C12—C13—C14—O14	−179.7 (2)	C24—C25—C26—C21	1.1 (3)
C12—C13—C14—C15	−0.7 (3)	C7^i—N1—C2—C3	175.20 (16)
O14—C14—C15—C16	179.66 (18)	N1—C2—C3—N4	62.7 (2)
C13—C14—C15—C16	0.7 (3)	C2—C3—N4—C5	−173.18 (16)
C14—C15—C16—C11	−0.2 (3)	C3—N4—C5—C52	68.8 (2)
C12—C11—C16—C15	−0.3 (3)	C3—N4—C5—C51	−53.3 (2)
S1—C11—C16—C15	179.60 (16)	C3—N4—C5—C6	−171.64 (16)
C11—S1—C21—C26	−93.67 (18)	N4—C5—C6—C7	−67.5 (2)
C11—S1—C21—C22	85.87 (18)	C52—C5—C6—C7	51.0 (2)
C26—C21—C22—C23	−0.9 (3)	C51—C5—C6—C7	171.46 (17)
S1—C21—C22—C23	179.51 (15)	C5—C6—C7—N1^i	57.3 (2)
C21—C22—C23—C24	1.5 (3)	C5—C6—C7—C71	179.08 (17)
C22—C23—C24—O24	177.86 (17)

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
N1—H1A···O1	0.90	1.85	2.733 (3)	168
N1—H1E···N4^i	0.90	2.05	2.792 (2)	139
O1—H1···O24	0.82	1.78	2.591 (3)	172
O14—H14···O24^ii	0.82	1.75	2.568 (2)	174

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

(3) Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane- 4,4'-tsulfonylbiphenol-methanol (1/2/2)

Crystal data

C16H38N4^2+·2(C12H9O4S^−)·2(CH4O)	? #Insert any comments here.
Mr = 849.09	Dx = 1.275 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.7736 (10) Å	Cell parameters from 25 reflections
b = 18.1167 (18) Å	θ = 8.4–13.4°
c = 11.5532 (14) Å	µ = 0.18 mm^−1
β = 101.136 (9)°	T = 294 K
V = 2212.5 (4) Å^3	Plate, colourless
Z = 2	0.42 × 0.33 × 0.12 mm
F(000) = 912

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.010
Radiation source: X-ray tube	θmax = 25.4°, θmin = 2.1°
Graphite monochromator	h = −13→12
θ/2θ scans	k = 0→21
4294 measured reflections	l = 0→13
4091 independent reflections	3 standard reflections every 120 min
2056 reflections with I > 2σ(I)	intensity decay: no decay, variation .5%

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)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0464P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
4091 reflections	Δρmax = 0.19 e Å^−3
266 parameters	Δρmin = −0.21 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: 0.0022 (6)

Special details

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 10.5555 (0.0029) x + 1.6199 (0.0352) y + 4.2169 (0.0141) z = 1.5960 (0.0300)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12

Rms deviation of fitted atoms = 0.0000

- 6.4110 (0.0092) x + 14.2835 (0.0122) y - 0.4393 (0.0133) z = 11.8572 (0.0117)

Angle to previous plane (with approximate e.s.d.) = 51.3 (1)

* -0.0013 (0.0019) C11 * -0.0015 (0.0020) C12 * 0.0058 (0.0020) C13 * -0.0075 (0.0019) C14 * 0.0048 (0.0020) C15 * -0.0004 (0.0019) C16 - 0.0506 (0.0036) S1 0.0074 (0.0037) O14

Rms deviation of fitted atoms = 0.0044

- 10.5555 (0.0029) x + 1.6199 (0.0352) y + 4.2169 (0.0141) z = 1.5960 (0.0300)

Angle to previous plane (with approximate e.s.d.) = 51.3 (1)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12

Rms deviation of fitted atoms = 0.0000

6.3894 (0.0089) x + 11.4828 (0.0144) y - 6.9518 (0.0097) z = 8.6481 (0.0129)

Angle to previous plane (with approximate e.s.d.) = 52.2 (1)

* 0.0058 (0.0018) C21 * -0.0077 (0.0018) C22 * 0.0037 (0.0018) C23 * 0.0022 (0.0018) C24 * -0.0041 (0.0019) C25 * 0.0001 (0.0019) C26 - 0.0130 (0.0034) S1 - 0.0034 (0.0035) O24

Rms deviation of fitted atoms = 0.0046

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

	x	y	z	Uiso*/Ueq
S1	0.12553 (6)	0.89368 (4)	0.34940 (7)	0.0536 (2)
O11	0.16511 (18)	0.95631 (11)	0.4244 (2)	0.0697 (6)
O12	0.07782 (18)	0.90481 (12)	0.22571 (18)	0.0744 (7)
O14	−0.25498 (17)	0.73319 (12)	0.55205 (18)	0.0585 (6)
O24	0.55381 (16)	0.68715 (10)	0.40051 (17)	0.0529 (5)
C11	0.0089 (2)	0.84660 (15)	0.4081 (2)	0.0430 (7)
C12	0.0087 (2)	0.85016 (16)	0.5273 (2)	0.0541 (8)
C13	−0.0800 (2)	0.81227 (17)	0.5732 (3)	0.0536 (8)
C14	−0.1693 (2)	0.76907 (15)	0.5021 (3)	0.0436 (7)
C15	−0.1696 (2)	0.76611 (15)	0.3826 (3)	0.0511 (8)
C16	−0.0804 (2)	0.80436 (15)	0.3360 (3)	0.0500 (7)
C21	0.2533 (2)	0.83232 (15)	0.3628 (2)	0.0439 (7)
C22	0.2566 (2)	0.77856 (16)	0.2790 (2)	0.0475 (7)
C23	0.3575 (2)	0.73059 (15)	0.2908 (2)	0.0465 (7)
C24	0.4580 (2)	0.73362 (15)	0.3884 (2)	0.0418 (7)
C25	0.4507 (2)	0.78793 (15)	0.4723 (2)	0.0480 (7)
C26	0.3513 (2)	0.83619 (15)	0.4601 (2)	0.0478 (7)
N1	0.44820 (18)	0.45871 (11)	0.33281 (17)	0.0393 (5)
C2	0.5272 (2)	0.39114 (15)	0.3512 (2)	0.0478 (7)
C3	0.6582 (2)	0.40787 (15)	0.4161 (2)	0.0480 (7)
N4	0.65792 (17)	0.43864 (11)	0.53316 (17)	0.0385 (5)
C5	0.7825 (2)	0.46690 (15)	0.5974 (2)	0.0431 (7)
C51	0.8873 (2)	0.40913 (17)	0.6078 (3)	0.0637 (9)
C52	0.8187 (3)	0.53498 (16)	0.5328 (3)	0.0591 (8)
C6	0.7658 (2)	0.48685 (15)	0.7233 (2)	0.0452 (7)
C7	0.6822 (2)	0.55211 (15)	0.7397 (2)	0.0445 (7)
C71	0.6739 (3)	0.56244 (17)	0.8682 (2)	0.0611 (8)
O1	0.55273 (19)	0.58024 (11)	0.2460 (2)	0.0651 (6)
C1	0.6612 (3)	0.58121 (18)	0.1940 (3)	0.0766 (10)
H14	−0.3122	0.7177	0.5004	0.088*
H12	0.0691	0.8784	0.5764	0.065*
H13	−0.0803	0.8156	0.6535	0.064*
H15	−0.2304	0.7381	0.3334	0.061*
H16	−0.0804	0.8017	0.2556	0.060*
H22	0.1906	0.7747	0.2143	0.057*
H23	0.3591	0.6953	0.2327	0.056*
H25	0.5151	0.7915	0.5384	0.058*
H26	0.3494	0.8719	0.5175	0.057*
H1A	0.4886	0.4929	0.2973	0.047*
H1E	0.4409	0.4767	0.4038	0.047*
H2A	0.5314	0.3694	0.2753	0.057*
H2B	0.4884	0.3554	0.3957	0.057*
H3A	0.7081	0.3629	0.4242	0.058*
H3B	0.6976	0.4428	0.3707	0.058*
H4A	0.6310	0.4035	0.5776	0.046*
H51A	0.8643	0.3665	0.6482	0.096*
H51B	0.9647	0.4294	0.6512	0.096*
H51C	0.8987	0.3952	0.5303	0.096*
H52A	0.7526	0.5712	0.5264	0.089*
H52B	0.8300	0.5211	0.4554	0.089*
H52C	0.8961	0.5554	0.5762	0.089*
H6A	0.7323	0.4437	0.7564	0.054*
H6B	0.8492	0.4961	0.7702	0.054*
H7	0.7187	0.5968	0.7122	0.053*
H71A	0.6205	0.6039	0.8756	0.092*
H71B	0.7570	0.5711	0.9138	0.092*
H71C	0.6390	0.5188	0.8965	0.092*
H1	0.5562	0.6146	0.2927	0.098*
H1P	0.6652	0.6273	0.1540	0.115*
H1Q	0.6565	0.5414	0.1385	0.115*
H1R	0.7355	0.5756	0.2543	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0417 (4)	0.0549 (5)	0.0651 (5)	0.0014 (4)	0.0125 (4)	0.0151 (5)
O11	0.0586 (13)	0.0428 (12)	0.1096 (18)	−0.0072 (10)	0.0212 (12)	−0.0038 (13)
O12	0.0545 (12)	0.1019 (18)	0.0669 (15)	0.0117 (12)	0.0120 (11)	0.0400 (13)
O14	0.0468 (12)	0.0661 (14)	0.0639 (14)	−0.0070 (10)	0.0137 (10)	0.0121 (12)
O24	0.0470 (11)	0.0442 (11)	0.0693 (14)	0.0017 (10)	0.0159 (10)	−0.0059 (10)
C11	0.0358 (14)	0.0457 (17)	0.0475 (18)	−0.0007 (13)	0.0080 (13)	0.0013 (14)
C12	0.0425 (16)	0.066 (2)	0.051 (2)	−0.0096 (15)	0.0012 (14)	−0.0031 (16)
C13	0.0474 (17)	0.073 (2)	0.0397 (17)	−0.0038 (16)	0.0053 (14)	0.0030 (16)
C14	0.0352 (15)	0.0465 (18)	0.0497 (19)	0.0038 (13)	0.0094 (14)	0.0055 (15)
C15	0.0447 (16)	0.0507 (18)	0.058 (2)	−0.0069 (14)	0.0092 (14)	−0.0109 (16)
C16	0.0490 (16)	0.0570 (19)	0.0464 (18)	−0.0013 (15)	0.0151 (14)	−0.0065 (16)
C21	0.0369 (14)	0.0482 (17)	0.0471 (18)	−0.0049 (13)	0.0095 (13)	0.0045 (15)
C22	0.0442 (16)	0.0549 (19)	0.0422 (17)	−0.0112 (14)	0.0050 (13)	0.0065 (16)
C23	0.0544 (17)	0.0437 (17)	0.0435 (18)	−0.0109 (14)	0.0147 (15)	−0.0040 (14)
C24	0.0408 (15)	0.0387 (16)	0.0484 (18)	−0.0080 (13)	0.0143 (14)	0.0018 (14)
C25	0.0383 (15)	0.0535 (19)	0.0489 (18)	−0.0039 (14)	0.0004 (13)	−0.0054 (15)
C26	0.0469 (16)	0.0503 (18)	0.0471 (18)	0.0001 (14)	0.0109 (14)	−0.0072 (15)
N1	0.0423 (12)	0.0420 (13)	0.0342 (12)	−0.0043 (10)	0.0090 (10)	−0.0067 (11)
C2	0.0549 (17)	0.0403 (16)	0.0479 (17)	0.0043 (14)	0.0094 (14)	−0.0084 (14)
C3	0.0463 (16)	0.0526 (18)	0.0453 (17)	0.0089 (14)	0.0093 (13)	−0.0094 (14)
N4	0.0389 (12)	0.0405 (13)	0.0379 (12)	−0.0043 (10)	0.0119 (10)	−0.0024 (11)
C5	0.0352 (14)	0.0462 (17)	0.0479 (17)	−0.0013 (13)	0.0084 (12)	0.0034 (14)
C51	0.0408 (16)	0.082 (2)	0.069 (2)	0.0125 (16)	0.0116 (15)	0.0064 (18)
C52	0.0552 (18)	0.068 (2)	0.0537 (19)	−0.0193 (16)	0.0099 (15)	0.0037 (17)
C6	0.0393 (15)	0.0519 (18)	0.0413 (16)	−0.0054 (13)	−0.0004 (12)	0.0040 (14)
C7	0.0475 (16)	0.0437 (16)	0.0382 (16)	−0.0109 (14)	−0.0016 (13)	−0.0036 (14)
C71	0.072 (2)	0.068 (2)	0.0407 (18)	−0.0038 (17)	0.0042 (15)	−0.0094 (17)
O1	0.0729 (14)	0.0505 (14)	0.0814 (17)	−0.0097 (11)	0.0388 (13)	−0.0123 (11)
C1	0.091 (2)	0.080 (3)	0.070 (2)	0.019 (2)	0.043 (2)	0.0108 (19)

Geometric parameters (Å, º)

S1—O12	1.436 (2)	C23—C24	1.406 (4)
S1—O11	1.441 (2)	C24—C25	1.394 (4)
S1—C21	1.753 (3)	C25—C26	1.369 (4)
S1—C11	1.759 (3)	N1—C2	1.483 (3)
O14—C14	1.347 (3)	N1—C7^i	1.503 (3)
O24—C24	1.318 (3)	C2—C3	1.496 (3)
C11—C16	1.377 (4)	C3—N4	1.463 (3)
C11—C12	1.379 (4)	N4—C5	1.493 (3)
C12—C13	1.364 (4)	C5—C51	1.527 (4)
C13—C14	1.381 (4)	C5—C52	1.530 (4)
C14—C15	1.380 (4)	C5—C6	1.543 (4)
C15—C16	1.376 (4)	C6—C7	1.520 (4)
C21—C22	1.378 (4)	C7—N1^i	1.503 (3)
C21—C26	1.387 (4)	C7—C71	1.516 (3)
C22—C23	1.377 (4)	O1—C1	1.413 (3)
O12—S1—O11	119.68 (14)	C22—C23—C24	121.7 (3)
O12—S1—C21	107.50 (13)	O24—C24—C25	121.7 (2)
O11—S1—C21	108.07 (13)	O24—C24—C23	121.7 (3)
O12—S1—C11	107.86 (13)	C25—C24—C23	116.5 (2)
O11—S1—C11	107.46 (13)	C26—C25—C24	121.8 (3)
C21—S1—C11	105.41 (13)	C25—C26—C21	120.6 (3)
C16—C11—C12	119.6 (2)	C2—N1—C7^i	114.91 (19)
C16—C11—S1	120.2 (2)	N1—C2—C3	111.4 (2)
C12—C11—S1	120.1 (2)	N4—C3—C2	111.7 (2)
C13—C12—C11	120.1 (3)	C3—N4—C5	115.30 (19)
C12—C13—C14	120.9 (3)	N4—C5—C51	112.6 (2)
O14—C14—C15	122.7 (3)	N4—C5—C52	108.9 (2)
O14—C14—C13	118.3 (3)	C51—C5—C52	109.7 (2)
C15—C14—C13	118.9 (3)	N4—C5—C6	106.92 (19)
C16—C15—C14	120.3 (3)	C51—C5—C6	107.8 (2)
C15—C16—C11	120.1 (3)	C52—C5—C6	111.0 (2)
C22—C21—C26	119.1 (3)	C7—C6—C5	118.7 (2)
C22—C21—S1	120.9 (2)	N1^i—C7—C71	109.7 (2)
C26—C21—S1	120.1 (2)	N1^i—C7—C6	110.0 (2)
C23—C22—C21	120.2 (3)	C71—C7—C6	111.5 (2)
O12—S1—C11—C16	23.8 (3)	C26—C21—C22—C23	−1.5 (4)
O11—S1—C11—C16	154.1 (2)	S1—C21—C22—C23	−179.8 (2)
C21—S1—C11—C16	−90.8 (2)	C21—C22—C23—C24	1.3 (4)
O12—S1—C11—C12	−158.0 (2)	C22—C23—C24—O24	179.2 (2)
O11—S1—C11—C12	−27.8 (3)	C22—C23—C24—C25	−0.3 (4)
C21—S1—C11—C12	87.3 (3)	O24—C24—C25—C26	−179.9 (2)
C16—C11—C12—C13	−0.3 (4)	C23—C24—C25—C26	−0.4 (4)
S1—C11—C12—C13	−178.5 (2)	C24—C25—C26—C21	0.2 (4)
C11—C12—C13—C14	1.0 (4)	C22—C21—C26—C25	0.7 (4)
C12—C13—C14—O14	−179.7 (3)	S1—C21—C26—C25	179.1 (2)
C12—C13—C14—C15	−1.6 (4)	C7^i—N1—C2—C3	175.7 (2)
O14—C14—C15—C16	179.5 (2)	N1—C2—C3—N4	60.9 (3)
C13—C14—C15—C16	1.5 (4)	C2—C3—N4—C5	−171.7 (2)
C14—C15—C16—C11	−0.8 (4)	C3—N4—C5—C51	−54.4 (3)
C12—C11—C16—C15	0.2 (4)	C3—N4—C5—C52	67.5 (3)
S1—C11—C16—C15	178.4 (2)	C3—N4—C5—C6	−172.6 (2)
O12—S1—C21—C22	−31.1 (3)	N4—C5—C6—C7	−68.4 (3)
O11—S1—C21—C22	−161.6 (2)	C51—C5—C6—C7	170.3 (2)
C11—S1—C21—C22	83.7 (2)	C52—C5—C6—C7	50.2 (3)
O12—S1—C21—C26	150.5 (2)	C5—C6—C7—N1^i	56.7 (3)
O11—S1—C21—C26	20.0 (3)	C5—C6—C7—C71	178.6 (2)
C11—S1—C21—C26	−94.6 (2)

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
N1—H1A···O1	0.90	1.87	2.749 (3)	166
N1—H1E···N4^i	0.90	2.08	2.801 (3)	137
O1—H1···O24	0.82	1.81	2.632 (3)	175
O14—H14···O24^ii	0.82	1.75	2.571 (3)	174
C2—H2B···O24^i	0.97	2.60	3.460 (3)	148
C16—H16···O12	0.93	2.60	2.946 (3)	103
C26—H26···O11	0.93	2.57	2.934 (3)	104
C52—H52C···O12^iii	0.96	2.46	3.398 (4)	167

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

(4) Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane- 3-hydroxybenzoic acid-methanol (1/2/2)

Crystal data

C16H38N4^2+·2(C7H5O3^−)·2(CH4O)	F(000) = 340
Mr = 624.81	? #Insert any comments here.
Triclinic, P1	Dx = 1.215 Mg m^−3
a = 8.0814 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1981 (12) Å	Cell parameters from 25 reflections
c = 10.7800 (16) Å	θ = 8.7–17.4°
α = 79.789 (10)°	µ = 0.09 mm^−1
β = 80.728 (10)°	T = 294 K
γ = 80.28 (1)°	Block, colourless
V = 853.89 (19) Å^3	0.42 × 0.29 × 0.21 mm
Z = 1

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: X-ray tube	θmax = 25.4°, θmin = 2.1°
Graphite monochromator	h = −9→9
θ/2θ scans	k = 0→12
3169 measured reflections	l = −12→13
3169 independent reflections	3 standard reflections every 120 min
1794 reflections with I > 2σ(I)	intensity decay: no decay, variation 1.0%

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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0589P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
3169 reflections	Δρmax = 0.17 e Å^−3
206 parameters	Δρmin = −0.14 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: 0.017 (4)

Special details

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 0.4190 (0.0052) x + 8.5094 (0.0045) y - 4.1027 (0.0083) z = 0.7116 (0.0023)

* -0.0038 (0.0018) C11 * 0.0001 (0.0016) C12 * -0.0013 (0.0015) C13 * 0.0031 (0.0017) C14 * -0.0004 (0.0016) C15 * -0.0008 (0.0017) C16 * 0.0031 (0.0013) C1 0.0698 (0.0028) O1 - 0.0319 (0.0030) O2 - 0.0187 (0.0031) O3

Rms deviation of fitted atoms = 0.0023

- 0.3482 (0.0096) x + 8.2795 (0.0063) y - 4.5396 (0.0102) z = 0.6108 (0.0065)

Angle to previous plane (with approximate e.s.d.) = 2.7 (1)

* -0.0071 (0.0018) C1 * 0.0020 (0.0005) C11 * 0.0026 (0.0007) O1 * 0.0026 (0.0007) O2

Rms deviation of fitted atoms = 0.0041

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

	x	y	z	Uiso*/Ueq
O1	0.47787 (18)	0.26972 (16)	0.32017 (15)	0.0462 (4)
O2	0.63698 (19)	0.18684 (19)	0.15680 (17)	0.0612 (5)
O3	−0.11098 (18)	0.20664 (17)	0.27105 (16)	0.0510 (5)
C1	0.4970 (3)	0.2153 (2)	0.2215 (2)	0.0393 (6)
C11	0.3430 (2)	0.18478 (19)	0.1757 (2)	0.0311 (5)
C12	0.1828 (2)	0.2100 (2)	0.2434 (2)	0.0351 (5)
C13	0.0424 (2)	0.1816 (2)	0.1993 (2)	0.0347 (5)
C14	0.0622 (3)	0.1292 (2)	0.0874 (2)	0.0395 (6)
C15	0.2219 (3)	0.1042 (2)	0.0201 (2)	0.0443 (6)
C16	0.3614 (3)	0.1321 (2)	0.0638 (2)	0.0378 (5)
N1	0.6562 (2)	0.48140 (17)	0.32951 (15)	0.0352 (4)
C2	0.8148 (3)	0.4710 (2)	0.3854 (2)	0.0396 (5)
C3	0.8140 (3)	0.3725 (2)	0.5072 (2)	0.0435 (6)
N4	0.6864 (2)	0.42249 (17)	0.60766 (16)	0.0360 (4)
C5	0.6756 (3)	0.3322 (2)	0.7330 (2)	0.0421 (6)
C51	0.6327 (3)	0.1976 (2)	0.7142 (3)	0.0623 (8)
C52	0.8402 (3)	0.3113 (3)	0.7913 (3)	0.0723 (9)
C6	0.5360 (3)	0.4017 (2)	0.8239 (2)	0.0422 (6)
C7	0.3546 (3)	0.4242 (2)	0.7943 (2)	0.0396 (5)
C71	0.2298 (3)	0.4802 (3)	0.9007 (2)	0.0558 (7)
O4	0.2704 (3)	0.22339 (19)	0.54747 (19)	0.0720 (6)
C41	0.2467 (5)	0.0892 (3)	0.5848 (3)	0.1010 (12)
H3	−0.1862	0.1979	0.2317	0.077*
H12	0.1693	0.2459	0.3185	0.042*
H14	−0.0316	0.1107	0.0574	0.047*
H15	0.2353	0.0684	−0.0550	0.053*
H16	0.4684	0.1154	0.0178	0.045*
H1E	0.5684	0.5085	0.3865	0.042*
H1A	0.6442	0.3987	0.3170	0.042*
H2A	0.8275	0.5589	0.4021	0.048*
H2B	0.9108	0.4421	0.3249	0.048*
H3A	0.7901	0.2870	0.4923	0.052*
H3B	0.9251	0.3577	0.5347	0.052*
H4A	0.7090	0.5025	0.6194	0.043*
H51A	0.5398	0.2132	0.6655	0.093*
H51B	0.6016	0.1458	0.7956	0.093*
H51C	0.7297	0.1490	0.6697	0.093*
H52A	0.9307	0.2682	0.7364	0.108*
H52B	0.8270	0.2557	0.8730	0.108*
H52C	0.8665	0.3970	0.8011	0.108*
H6A	0.5378	0.3489	0.9080	0.051*
H6B	0.5659	0.4887	0.8284	0.051*
H7	0.3250	0.3377	0.7844	0.048*
H71A	0.2598	0.5635	0.9136	0.084*
H71B	0.2337	0.4166	0.9778	0.084*
H71C	0.1174	0.4957	0.8778	0.084*
H4	0.3396	0.2301	0.4829	0.108*
H41A	0.3545	0.0327	0.5786	0.151*
H41B	0.1770	0.0656	0.5303	0.151*
H41C	0.1921	0.0768	0.6711	0.151*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0362 (9)	0.0569 (10)	0.0531 (11)	−0.0154 (7)	−0.0104 (8)	−0.0164 (9)
O2	0.0249 (9)	0.0955 (14)	0.0706 (13)	−0.0115 (8)	−0.0062 (8)	−0.0302 (10)
O3	0.0263 (8)	0.0711 (12)	0.0627 (11)	−0.0086 (8)	−0.0046 (8)	−0.0288 (9)
C1	0.0284 (13)	0.0390 (13)	0.0520 (16)	−0.0068 (10)	−0.0113 (11)	−0.0041 (11)
C11	0.0256 (11)	0.0287 (11)	0.0395 (13)	−0.0045 (8)	−0.0091 (9)	−0.0020 (9)
C12	0.0292 (11)	0.0397 (13)	0.0394 (13)	−0.0055 (9)	−0.0084 (10)	−0.0102 (10)
C13	0.0225 (11)	0.0368 (12)	0.0458 (14)	−0.0028 (9)	−0.0080 (10)	−0.0077 (10)
C14	0.0326 (13)	0.0447 (14)	0.0477 (15)	−0.0094 (10)	−0.0136 (11)	−0.0136 (11)
C15	0.0432 (14)	0.0513 (15)	0.0428 (14)	−0.0104 (11)	−0.0032 (11)	−0.0184 (11)
C16	0.0302 (12)	0.0407 (13)	0.0431 (14)	−0.0069 (9)	−0.0017 (10)	−0.0097 (11)
N1	0.0352 (10)	0.0400 (10)	0.0314 (10)	−0.0076 (8)	−0.0043 (8)	−0.0068 (8)
C2	0.0327 (12)	0.0505 (14)	0.0383 (13)	−0.0092 (10)	−0.0050 (10)	−0.0109 (11)
C3	0.0369 (13)	0.0547 (15)	0.0376 (14)	0.0018 (11)	−0.0092 (10)	−0.0077 (11)
N4	0.0402 (10)	0.0381 (11)	0.0302 (10)	−0.0052 (8)	−0.0068 (8)	−0.0058 (8)
C5	0.0438 (13)	0.0458 (14)	0.0357 (13)	−0.0040 (11)	−0.0112 (11)	−0.0004 (11)
C51	0.0751 (19)	0.0445 (16)	0.0588 (18)	−0.0035 (13)	0.0026 (15)	−0.0007 (13)
C52	0.0541 (17)	0.109 (3)	0.0469 (17)	0.0013 (16)	−0.0197 (14)	0.0063 (16)
C6	0.0519 (15)	0.0468 (14)	0.0280 (12)	−0.0097 (11)	−0.0115 (11)	0.0020 (10)
C7	0.0461 (13)	0.0395 (13)	0.0323 (13)	−0.0094 (10)	−0.0036 (10)	−0.0011 (10)
C71	0.0574 (16)	0.0660 (17)	0.0369 (14)	−0.0035 (13)	0.0032 (12)	−0.0028 (12)
O4	0.0839 (15)	0.0652 (13)	0.0659 (14)	−0.0070 (10)	−0.0030 (11)	−0.0179 (10)
C41	0.124 (3)	0.074 (2)	0.098 (3)	−0.016 (2)	−0.002 (2)	−0.004 (2)

Geometric parameters (Å, º)

O1—C1	1.261 (3)	N1—C7^i	1.506 (3)
O2—C1	1.248 (3)	C2—C3	1.505 (3)
O3—C13	1.361 (2)	C3—N4	1.468 (3)
C1—C11	1.508 (3)	N4—C5	1.493 (3)
C11—C16	1.382 (3)	C5—C51	1.526 (3)
C11—C12	1.387 (3)	C5—C52	1.529 (3)
C12—C13	1.389 (3)	C5—C6	1.535 (3)
C13—C14	1.379 (3)	C6—C7	1.522 (3)
C14—C15	1.381 (3)	C7—N1^i	1.506 (3)
C15—C16	1.379 (3)	C7—C71	1.525 (3)
N1—C2	1.482 (2)	O4—C41	1.392 (3)
O2—C1—O1	123.9 (2)	N1—C2—C3	111.30 (17)
O2—C1—C11	117.1 (2)	N4—C3—C2	111.17 (18)
O1—C1—C11	119.00 (19)	C3—N4—C5	115.45 (16)
C16—C11—C12	119.40 (18)	N4—C5—C51	108.61 (18)
C16—C11—C1	119.50 (18)	N4—C5—C52	111.95 (19)
C12—C11—C1	121.09 (19)	C51—C5—C52	110.5 (2)
C11—C12—C13	120.2 (2)	N4—C5—C6	107.40 (17)
O3—C13—C14	122.77 (18)	C51—C5—C6	111.06 (18)
O3—C13—C12	117.34 (19)	C52—C5—C6	107.30 (19)
C14—C13—C12	119.89 (19)	C7—C6—C5	118.41 (18)
C13—C14—C15	119.9 (2)	N1^i—C7—C6	108.95 (17)
C16—C15—C14	120.3 (2)	N1^i—C7—C71	110.52 (18)
C15—C16—C11	120.3 (2)	C6—C7—C71	111.69 (19)
C2—N1—C7^i	115.56 (16)
O2—C1—C11—C16	−2.2 (3)	C1—C11—C16—C15	−179.7 (2)
O1—C1—C11—C16	176.4 (2)	C7^i—N1—C2—C3	−178.95 (18)
O2—C1—C11—C12	178.4 (2)	N1—C2—C3—N4	−67.5 (2)
O1—C1—C11—C12	−3.0 (3)	C2—C3—N4—C5	−179.80 (17)
C16—C11—C12—C13	0.4 (3)	C3—N4—C5—C51	−59.7 (2)
C1—C11—C12—C13	179.76 (19)	C3—N4—C5—C52	62.6 (3)
C11—C12—C13—O3	178.98 (19)	C3—N4—C5—C6	−179.86 (17)
C11—C12—C13—C14	−0.5 (3)	N4—C5—C6—C7	64.5 (2)
O3—C13—C14—C15	−179.0 (2)	C51—C5—C6—C7	−54.2 (3)
C12—C13—C14—C15	0.5 (3)	C52—C5—C6—C7	−175.0 (2)
C13—C14—C15—C16	−0.4 (3)	C5—C6—C7—N1^i	−63.8 (2)
C14—C15—C16—C11	0.3 (3)	C5—C6—C7—C71	173.87 (19)
C12—C11—C16—C15	−0.3 (3)

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
N1—H1A···O1	0.90	2.03	2.815 (2)	145
N1—H1A···O3^ii	0.90	2.59	3.202 (2)	126
N1—H1E···N4^i	0.90	2.06	2.793 (2)	138
O3—H3···O2^iii	0.82	1.78	2.596 (2)	175
O4—H4···O1	0.82	1.94	2.752 (3)	171
C2—H2A···O4^i	0.97	2.36	3.260 (3)	155

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

(5) Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane- 4-hydroxybenzoic acid-methanol (1/2/1)

Crystal data

C16H38N4^2+·2(C7H5O3^−)·CH4O	F(000) = 644
Mr = 592.77	#all measured reflections were used in the cell-dimension refinement
Triclinic, P1	Dx = 1.216 Mg m^−3
a = 9.4481 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8905 (6) Å	Cell parameters from 18522 reflections
c = 18.0942 (12) Å	θ = 4.2–26.4°
α = 88.704 (5)°	µ = 0.09 mm^−1
β = 78.675 (4)°	T = 100 K
γ = 77.525 (4)°	Block, colourless
V = 1618.43 (19) Å^3	0.35 × 0.20 × 0.20 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	2949 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.091
Graphite monochromator	θmax = 26.4°, θmin = 4.2°
ω scans	h = 0→11
18522 measured reflections	k = −11→12
6587 independent reflections	l = −22→22

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)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0462P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.84	(Δ/σ)max = 0.001
6587 reflections	Δρmax = 0.24 e Å^−3
394 parameters	Δρmin = −0.22 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: 0.0048 (11)

Special details

Experimental. All measured reflections were used in the refinement to determine the cell data. Measurements made at the start and end of the data collection showed that there was no measurable crystal decay at 100 K.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N11	0.0581 (2)	1.14634 (18)	0.05413 (12)	0.0282 (5)
C12	−0.0809 (3)	1.2146 (2)	0.10162 (15)	0.0323 (7)
C13	−0.1717 (3)	1.1116 (2)	0.13351 (14)	0.0314 (7)
N14	−0.1966 (2)	1.02788 (18)	0.07178 (11)	0.0273 (5)
C15	−0.2930 (3)	0.9248 (2)	0.09334 (15)	0.0300 (6)
C151	−0.4463 (3)	1.0006 (3)	0.13263 (16)	0.0389 (7)
C152	−0.2226 (5)	0.8143 (4)	0.1439 (2)	0.0301 (13)	0.584 (5)
C16	−0.3022 (3)	0.8537 (2)	0.02107 (15)	0.0323 (7)
C17	−0.1611 (3)	0.7632 (2)	−0.02441 (16)	0.0337 (7)
C171	−0.2027 (3)	0.6843 (3)	−0.08635 (17)	0.0464 (8)
C172	−0.0866 (7)	0.6546 (6)	0.0335 (4)	0.050 (2)	0.416 (5)
N21	0.5580 (2)	0.35942 (19)	0.57514 (12)	0.0305 (5)
C22	0.7120 (3)	0.3734 (2)	0.57168 (15)	0.0296 (6)
C23	0.7908 (3)	0.3797 (2)	0.49110 (15)	0.0317 (7)
N24	0.7259 (2)	0.51046 (18)	0.45557 (11)	0.0269 (5)
C25	0.7840 (3)	0.5265 (2)	0.37250 (14)	0.0288 (6)
C251	0.9407 (3)	0.5502 (3)	0.36330 (16)	0.0384 (7)
C252	0.7816 (3)	0.3989 (2)	0.32830 (15)	0.0409 (7)
C26	0.6832 (3)	0.6570 (2)	0.34857 (15)	0.0326 (7)
C27	0.5235 (3)	0.6509 (2)	0.34705 (15)	0.0316 (7)
C271	0.4531 (3)	0.7739 (3)	0.30435 (16)	0.0429 (8)
O31	0.32303 (19)	0.79367 (16)	0.02026 (10)	0.0366 (5)
O32	0.13097 (19)	0.84985 (15)	0.11570 (10)	0.0322 (5)
O34	0.51690 (18)	0.31050 (16)	0.23799 (10)	0.0323 (4)
C31	0.3188 (3)	0.6491 (2)	0.12526 (14)	0.0247 (6)
C32	0.4594 (3)	0.5722 (2)	0.09665 (15)	0.0286 (6)
C33	0.5239 (3)	0.4601 (2)	0.13438 (15)	0.0302 (6)
C34	0.4475 (3)	0.4208 (2)	0.20190 (14)	0.0252 (6)
C35	0.3058 (3)	0.4930 (2)	0.23037 (14)	0.0286 (6)
C36	0.2424 (3)	0.6055 (2)	0.19213 (14)	0.0284 (6)
C37	0.2528 (3)	0.7722 (2)	0.08461 (15)	0.0287 (6)
O41	0.36644 (19)	0.28621 (16)	0.37491 (10)	0.0328 (4)
O42	0.19257 (18)	0.28052 (16)	0.47672 (10)	0.0352 (5)
O44	0.00216 (18)	−0.11098 (16)	0.25975 (10)	0.0332 (5)
C41	0.1857 (3)	0.1533 (2)	0.36872 (15)	0.0273 (6)
C42	0.2264 (3)	0.1330 (2)	0.29082 (15)	0.0301 (6)
C43	0.1656 (3)	0.0463 (2)	0.25408 (15)	0.0315 (7)
C44	0.0645 (3)	−0.0235 (2)	0.29374 (15)	0.0267 (6)
C45	0.0227 (3)	−0.0061 (2)	0.37097 (15)	0.0317 (7)
C46	0.0836 (3)	0.0838 (2)	0.40718 (15)	0.0304 (6)
C47	0.2520 (3)	0.2466 (2)	0.40966 (16)	0.0287 (6)
O1	0.5917 (2)	0.16624 (17)	0.44604 (12)	0.0456 (5)
C1	0.6208 (3)	0.0293 (3)	0.4182 (2)	0.0585 (10)
H11A	0.1045	1.0792	0.0809	0.034*
H12A	−0.1366	1.2814	0.0722	0.039*
H12B	−0.0607	1.2643	0.1426	0.039*
H13A	−0.1209	1.0508	0.1673	0.038*
H13B	−0.2661	1.1602	0.1622	0.038*
H14E	−0.1078	0.9816	0.0470	0.033*
H14A	−0.2366	1.0868	0.0391	0.033*
H15A	−0.4873	1.0691	0.0997	0.058*
H15B	−0.4393	1.0450	0.1780	0.058*
H15C	−0.5091	0.9356	0.1449	0.058*
H15D	−0.1264	0.7682	0.1177	0.045*	0.584 (5)
H15E	−0.2837	0.7479	0.1565	0.045*	0.584 (5)
H15F	−0.2138	0.8576	0.1893	0.045*	0.584 (5)
H16A	−0.3407	0.9251	−0.0119	0.039*
H16B	−0.3746	0.7964	0.0341	0.039*
H17A	−0.1149	0.6268	−0.1151	0.070*
H17B	−0.2496	0.7493	−0.1190	0.070*
H17C	−0.2693	0.6275	−0.0636	0.070*
H17D	0.0026	0.5964	0.0065	0.075*	0.416 (5)
H17E	−0.1546	0.5985	0.0553	0.075*	0.416 (5)
H17F	−0.0638	0.7051	0.0727	0.075*	0.416 (5)
H21A	0.5591	0.2833	0.5485	0.037*
H22A	0.7644	0.2950	0.5959	0.036*
H22B	0.7116	0.4570	0.5988	0.036*
H23A	0.8948	0.3753	0.4897	0.038*
H23B	0.7826	0.3007	0.4627	0.038*
H24A	0.7405	0.5822	0.4807	0.032*
H24E	0.6276	0.5174	0.4623	0.032*
H25A	0.9392	0.6316	0.3916	0.058*
H25B	0.9792	0.5623	0.3110	0.058*
H25C	1.0024	0.4716	0.3816	0.058*
H25D	0.6820	0.3861	0.3352	0.061*
H25E	0.8427	0.3192	0.3460	0.061*
H25F	0.8186	0.4106	0.2758	0.061*
H26A	0.6810	0.7325	0.3824	0.039*
H26B	0.7289	0.6805	0.2985	0.039*
H27	0.5257	0.5663	0.3193	0.038*
H27A	0.3530	0.7691	0.3035	0.064*
H27B	0.5082	0.7713	0.2536	0.064*
H27C	0.4537	0.8585	0.3291	0.064*
H34	0.4658	0.3028	0.2794	0.048*
H32	0.5115	0.5967	0.0510	0.034*
H33	0.6189	0.4107	0.1144	0.036*
H35	0.2529	0.4661	0.2751	0.034*
H36	0.1465	0.6532	0.2116	0.034*
H44	0.0478	−0.1281	0.2164	0.050*
H42	0.2954	0.1786	0.2633	0.036*
H43	0.1931	0.0347	0.2020	0.038*
H45	−0.0448	−0.0533	0.3984	0.038*
H46	0.0541	0.0971	0.4591	0.036*
H1	0.5252	0.2139	0.4278	0.068*
H1A	0.6820	−0.0304	0.4475	0.088*
H1B	0.6711	0.0250	0.3665	0.088*
H1C	0.5294	−0.0001	0.4217	0.088*
H15	−0.2496	0.8560	0.1270	0.036*	0.416 (5)
H17	−0.1154	0.6960	0.0093	0.040*	0.584 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0255 (12)	0.0263 (11)	0.0328 (14)	−0.0053 (9)	−0.0061 (11)	−0.0016 (10)
C12	0.0285 (15)	0.0329 (14)	0.0342 (18)	−0.0049 (12)	−0.0044 (13)	−0.0064 (13)
C13	0.0312 (16)	0.0324 (14)	0.0284 (16)	−0.0023 (11)	−0.0048 (13)	−0.0042 (12)
N14	0.0248 (12)	0.0303 (11)	0.0254 (13)	−0.0038 (9)	−0.0041 (10)	0.0007 (10)
C15	0.0252 (15)	0.0324 (14)	0.0333 (17)	−0.0083 (11)	−0.0062 (13)	0.0067 (13)
C151	0.0303 (16)	0.0460 (16)	0.0394 (19)	−0.0123 (13)	−0.0010 (14)	0.0059 (14)
C152	0.033 (3)	0.039 (3)	0.023 (3)	−0.017 (2)	−0.007 (2)	0.003 (2)
C16	0.0288 (15)	0.0349 (14)	0.0367 (18)	−0.0127 (11)	−0.0083 (14)	0.0009 (13)
C17	0.0296 (16)	0.0324 (14)	0.0408 (19)	−0.0110 (12)	−0.0053 (14)	−0.0037 (13)
C171	0.0424 (18)	0.0471 (17)	0.054 (2)	−0.0208 (14)	−0.0059 (16)	−0.0112 (16)
C172	0.043 (5)	0.046 (4)	0.059 (6)	−0.008 (3)	−0.007 (4)	0.005 (4)
N21	0.0298 (13)	0.0329 (12)	0.0300 (14)	−0.0093 (9)	−0.0061 (11)	0.0005 (10)
C22	0.0281 (15)	0.0289 (13)	0.0331 (17)	−0.0053 (11)	−0.0104 (14)	0.0044 (12)
C23	0.0284 (15)	0.0285 (14)	0.0368 (18)	−0.0033 (11)	−0.0063 (14)	0.0018 (13)
N24	0.0244 (12)	0.0264 (11)	0.0309 (14)	−0.0072 (9)	−0.0054 (11)	−0.0033 (10)
C25	0.0311 (16)	0.0312 (14)	0.0240 (16)	−0.0102 (11)	−0.0014 (13)	−0.0018 (12)
C251	0.0300 (16)	0.0464 (16)	0.0360 (19)	−0.0065 (12)	−0.0013 (14)	0.0026 (14)
C252	0.0492 (18)	0.0369 (15)	0.0356 (18)	−0.0064 (13)	−0.0084 (15)	−0.0057 (13)
C26	0.0374 (17)	0.0358 (14)	0.0251 (16)	−0.0111 (12)	−0.0040 (14)	0.0020 (12)
C27	0.0345 (16)	0.0340 (15)	0.0276 (17)	−0.0094 (12)	−0.0078 (14)	0.0059 (13)
C271	0.0388 (18)	0.0498 (17)	0.042 (2)	−0.0106 (13)	−0.0122 (16)	0.0167 (15)
O31	0.0376 (11)	0.0419 (11)	0.0276 (12)	−0.0070 (8)	−0.0030 (10)	0.0080 (9)
O32	0.0345 (11)	0.0306 (9)	0.0289 (11)	−0.0013 (8)	−0.0069 (9)	0.0018 (8)
O34	0.0294 (10)	0.0329 (9)	0.0315 (12)	−0.0040 (8)	−0.0021 (9)	0.0042 (9)
C31	0.0292 (15)	0.0231 (13)	0.0231 (15)	−0.0078 (11)	−0.0055 (13)	−0.0013 (11)
C32	0.0288 (15)	0.0315 (14)	0.0256 (16)	−0.0110 (11)	−0.0001 (13)	−0.0008 (12)
C33	0.0253 (15)	0.0298 (14)	0.0325 (18)	−0.0043 (11)	−0.0002 (14)	0.0010 (13)
C34	0.0275 (15)	0.0206 (13)	0.0279 (16)	−0.0042 (11)	−0.0076 (13)	−0.0013 (12)
C35	0.0289 (15)	0.0339 (14)	0.0224 (16)	−0.0090 (12)	−0.0010 (13)	0.0023 (12)
C36	0.0243 (15)	0.0299 (14)	0.0286 (17)	−0.0011 (11)	−0.0044 (13)	−0.0022 (13)
C37	0.0319 (16)	0.0312 (14)	0.0261 (17)	−0.0103 (12)	−0.0093 (14)	0.0004 (13)
O41	0.0341 (11)	0.0356 (10)	0.0306 (12)	−0.0115 (8)	−0.0068 (10)	0.0035 (8)
O42	0.0379 (11)	0.0407 (11)	0.0270 (12)	−0.0120 (8)	−0.0014 (10)	−0.0078 (9)
O44	0.0371 (11)	0.0356 (10)	0.0274 (12)	−0.0115 (8)	−0.0034 (9)	−0.0030 (9)
C41	0.0267 (15)	0.0258 (13)	0.0283 (16)	−0.0031 (11)	−0.0057 (13)	0.0006 (12)
C42	0.0306 (15)	0.0329 (14)	0.0265 (16)	−0.0081 (11)	−0.0038 (13)	0.0022 (12)
C43	0.0347 (16)	0.0363 (15)	0.0233 (16)	−0.0079 (12)	−0.0052 (14)	0.0005 (13)
C44	0.0251 (15)	0.0272 (13)	0.0277 (17)	−0.0040 (11)	−0.0065 (13)	0.0000 (12)
C45	0.0308 (15)	0.0338 (15)	0.0310 (17)	−0.0118 (12)	−0.0018 (14)	0.0001 (13)
C46	0.0345 (16)	0.0324 (14)	0.0225 (16)	−0.0036 (12)	−0.0054 (13)	0.0006 (12)
C47	0.0289 (16)	0.0248 (14)	0.0311 (18)	−0.0012 (11)	−0.0083 (14)	0.0039 (13)
O1	0.0483 (14)	0.0393 (11)	0.0524 (14)	−0.0072 (9)	−0.0192 (11)	−0.0063 (10)
C1	0.052 (2)	0.0422 (17)	0.079 (3)	−0.0040 (14)	−0.0126 (19)	−0.0084 (17)

Geometric parameters (Å, º)

N11—C12	1.456 (3)	C27—C271	1.526 (3)
N11—C17^i	1.479 (3)	O31—C37	1.260 (3)
C12—C13	1.504 (3)	O32—C37	1.270 (3)
C13—N14	1.489 (3)	O34—C34	1.369 (3)
N14—C15	1.505 (3)	C31—C32	1.387 (3)
C15—C151	1.522 (3)	C31—C36	1.392 (3)
C15—C16	1.525 (3)	C31—C37	1.491 (3)
C15—C152	1.535 (5)	C32—C33	1.380 (3)
C16—C17	1.531 (3)	C33—C34	1.385 (3)
C17—N11^i	1.479 (3)	C34—C35	1.379 (3)
C17—C171	1.537 (3)	C35—C36	1.384 (3)
C17—C172	1.631 (7)	O41—C47	1.274 (3)
N21—C27^ii	1.479 (3)	O42—C47	1.253 (3)
N21—C22	1.480 (3)	O44—C44	1.364 (3)
C22—C23	1.508 (3)	C41—C46	1.374 (3)
C23—N24	1.495 (3)	C41—C42	1.393 (3)
N24—C25	1.513 (3)	C41—C47	1.502 (3)
C25—C252	1.516 (3)	C42—C43	1.377 (3)
C25—C251	1.525 (3)	C43—C44	1.377 (3)
C25—C26	1.538 (3)	C44—C45	1.380 (3)
C26—C27	1.529 (3)	C45—C46	1.395 (3)
C27—N21^ii	1.479 (3)	O1—C1	1.407 (3)
C12—N11—C17^i	115.79 (18)	N21^ii—C27—C26	109.6 (2)
N11—C12—C13	111.26 (19)	C271—C27—C26	110.0 (2)
N14—C13—C12	110.4 (2)	C32—C31—C36	117.4 (2)
C13—N14—C15	117.6 (2)	C32—C31—C37	120.6 (2)
N14—C15—C151	109.23 (18)	C36—C31—C37	122.0 (2)
N14—C15—C16	107.6 (2)	C33—C32—C31	121.5 (3)
C151—C15—C16	110.1 (2)	C32—C33—C34	120.1 (2)
N14—C15—C152	110.0 (2)	O34—C34—C35	122.4 (2)
C151—C15—C152	111.4 (3)	O34—C34—C33	118.1 (2)
C16—C15—C152	108.3 (2)	C35—C34—C33	119.5 (2)
C15—C16—C17	118.5 (2)	C34—C35—C36	119.8 (3)
N11^i—C17—C16	108.15 (18)	C35—C36—C31	121.6 (2)
N11^i—C17—C171	113.4 (2)	O31—C37—O32	123.3 (2)
C16—C17—C171	108.7 (2)	O31—C37—C31	117.2 (2)
N11^i—C17—C172	108.6 (3)	O32—C37—C31	119.5 (2)
C16—C17—C172	107.5 (3)	C46—C41—C42	117.7 (2)
C171—C17—C172	110.2 (3)	C46—C41—C47	120.9 (2)
C27^ii—N21—C22	113.2 (2)	C42—C41—C47	121.4 (2)
N21—C22—C23	110.9 (2)	C43—C42—C41	120.7 (3)
N24—C23—C22	110.77 (19)	C44—C43—C42	120.6 (2)
C23—N24—C25	117.16 (18)	O44—C44—C43	122.6 (2)
N24—C25—C252	110.4 (2)	O44—C44—C45	117.5 (2)
N24—C25—C251	108.0 (2)	C43—C44—C45	119.9 (2)
C252—C25—C251	111.1 (2)	C44—C45—C46	118.7 (2)
N24—C25—C26	106.02 (18)	C41—C46—C45	122.2 (2)
C252—C25—C26	111.8 (2)	O42—C47—O41	123.2 (2)
C251—C25—C26	109.2 (2)	O42—C47—C41	118.2 (2)
C27—C26—C25	117.8 (2)	O41—C47—C41	118.6 (2)
N21^ii—C27—C271	113.9 (2)
C17^i—N11—C12—C13	−175.6 (2)	C32—C33—C34—O34	−178.9 (2)
N11—C12—C13—N14	−55.6 (3)	C32—C33—C34—C35	1.2 (3)
C12—C13—N14—C15	−176.63 (19)	O34—C34—C35—C36	178.7 (2)
C13—N14—C15—C151	60.0 (3)	C33—C34—C35—C36	−1.4 (3)
C13—N14—C15—C16	179.62 (18)	C34—C35—C36—C31	−0.4 (3)
C13—N14—C15—C152	−62.5 (3)	C32—C31—C36—C35	2.3 (3)
N14—C15—C16—C17	65.1 (3)	C37—C31—C36—C35	−178.5 (2)
C151—C15—C16—C17	−175.9 (2)	C32—C31—C37—O31	7.4 (3)
C152—C15—C16—C17	−53.9 (3)	C36—C31—C37—O31	−171.8 (2)
C15—C16—C17—N11^i	−65.9 (3)	C32—C31—C37—O32	−172.4 (2)
C15—C16—C17—C171	170.6 (2)	C36—C31—C37—O32	8.5 (3)
C15—C16—C17—C172	51.2 (4)	C46—C41—C42—C43	0.1 (3)
C27^ii—N21—C22—C23	178.51 (19)	C47—C41—C42—C43	179.5 (2)
N21—C22—C23—N24	67.4 (2)	C41—C42—C43—C44	−0.7 (3)
C22—C23—N24—C25	−174.68 (19)	C42—C43—C44—O44	−179.6 (2)
C23—N24—C25—C252	50.2 (3)	C42—C43—C44—C45	0.4 (4)
C23—N24—C25—C251	−71.5 (2)	O44—C44—C45—C46	−179.44 (19)
C23—N24—C25—C26	171.52 (18)	C43—C44—C45—C46	0.6 (3)
N24—C25—C26—C27	−68.9 (3)	C42—C41—C46—C45	0.9 (4)
C252—C25—C26—C27	51.5 (3)	C47—C41—C46—C45	−178.5 (2)
C251—C25—C26—C27	174.9 (2)	C44—C45—C46—C41	−1.3 (4)
C25—C26—C27—N21^ii	67.9 (3)	C46—C41—C47—O42	−13.4 (3)
C25—C26—C27—C271	−166.2 (2)	C42—C41—C47—O42	167.2 (2)
C36—C31—C32—C33	−2.5 (3)	C46—C41—C47—O41	165.9 (2)
C37—C31—C32—C33	178.3 (2)	C42—C41—C47—O41	−13.5 (3)
C31—C32—C33—C34	0.8 (3)

Symmetry codes: (i) −x, −y+2, −z; (ii) −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···O41	0.82	1.94	2.740 (3)	167
N11—H11A···O32	0.90	2.31	3.098 (2)	145
N14—H14A···O31^i	0.90	1.76	2.656 (3)	177
N14—H14E···N11	0.90	2.51	2.857 (3)	103
N14—H14E···N11^i	0.90	2.16	2.811 (3)	128
N21—H21A···O1	0.90	2.14	2.976 (3)	154
N24—H24A···O42^ii	0.90	1.86	2.746 (2)	169
N24—H24E···N21	0.90	2.61	2.993 (3)	107
N24—H24E···N21^ii	0.90	2.13	2.867 (3)	139
O34—H34···O41	0.82	1.82	2.637 (3)	175
O44—H44···O32^iii	0.82	1.83	2.650 (3)	173

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

(6) Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane- phenylphosphonic acid-water (1/4/2)

Crystal data

C16H40N4^4+·4(C6H6O3P^−)·2(H2O)	#all measured reflections were used in the cell-dimension refinement
Mr = 952.86	Dx = 1.344 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7391 (2) Å	Cell parameters from 22140 reflections
b = 26.1558 (7) Å	θ = 4.1–26.4°
c = 10.7871 (2) Å	µ = 0.23 mm^−1
β = 107.267 (13)°	T = 100 K
V = 2354.57 (9) Å^3	Block, colourless
Z = 2	0.30 × 0.25 × 0.15 mm
F(000) = 1016

Data collection

Nonius KappaCCD diffractometer	3777 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.065
Graphite monochromator	θmax = 26.4°, θmin = 4.1°
ω scans	h = −10→10
22140 measured reflections	k = −32→32
4796 independent reflections	l = −13→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.036P)^2 + 1.8098P] where P = (Fo^2 + 2Fc^2)/3
4796 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.30 e Å^−3
2 restraints	Δρmin = −0.50 e Å^−3

Special details

Experimental. ? #Insert any special details here.

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

	x	y	z	Uiso*/Ueq
N1	0.22188 (19)	0.45794 (6)	0.39406 (15)	0.0168 (4)
C2	0.2388 (2)	0.46753 (8)	0.26172 (18)	0.0192 (4)
C3	0.3886 (2)	0.49741 (8)	0.26343 (19)	0.0186 (4)
N4	0.36879 (18)	0.55320 (6)	0.28357 (16)	0.0161 (3)
C5	0.5034 (2)	0.58926 (8)	0.27940 (19)	0.0187 (4)
C51	0.4413 (3)	0.64264 (8)	0.2964 (2)	0.0242 (5)
C52	0.5293 (3)	0.58504 (9)	0.1455 (2)	0.0254 (5)
C6	0.6615 (2)	0.57577 (8)	0.38366 (18)	0.0184 (4)
C7	0.6654 (2)	0.58190 (8)	0.52680 (19)	0.0174 (4)
C71	0.7214 (3)	0.63440 (8)	0.5836 (2)	0.0220 (4)
P1	0.17496 (6)	0.58371 (2)	0.56751 (5)	0.01579 (13)
O11	0.03695 (16)	0.61071 (6)	0.46200 (13)	0.0212 (3)
O12	0.27633 (15)	0.55078 (5)	0.50622 (13)	0.0176 (3)
O13	0.10300 (16)	0.55628 (6)	0.65931 (13)	0.0200 (3)
C11	0.3037 (2)	0.63435 (8)	0.65256 (19)	0.0176 (4)
C12	0.3067 (2)	0.68168 (8)	0.5937 (2)	0.0225 (4)
C13	0.4092 (3)	0.72019 (9)	0.6575 (2)	0.0284 (5)
C14	0.5116 (3)	0.71150 (9)	0.7808 (2)	0.0307 (5)
C15	0.5113 (3)	0.66464 (9)	0.8408 (2)	0.0276 (5)
C16	0.4071 (2)	0.62632 (8)	0.7779 (2)	0.0221 (4)
P2	−0.00716 (6)	0.60642 (2)	0.09060 (5)	0.01818 (13)
O21	−0.17523 (16)	0.58084 (6)	0.02509 (14)	0.0232 (3)
O22	0.12444 (16)	0.57146 (6)	0.07621 (13)	0.0214 (3)
O23	0.0103 (2)	0.62282 (6)	0.22699 (14)	0.0297 (4)
C21	−0.0122 (2)	0.66266 (8)	−0.00639 (19)	0.0191 (4)
C22	0.0615 (3)	0.66309 (9)	−0.1044 (2)	0.0261 (5)
C23	0.0650 (3)	0.70769 (9)	−0.1743 (2)	0.0303 (5)
C24	−0.0030 (3)	0.75197 (9)	−0.1455 (2)	0.0280 (5)
C25	−0.0777 (3)	0.75181 (9)	−0.0495 (2)	0.0280 (5)
C26	−0.0834 (3)	0.70746 (8)	0.0195 (2)	0.0236 (5)
O1	−0.20958 (19)	0.48739 (6)	0.09896 (14)	0.0248 (3)
H1A	0.1183	0.4478	0.3849	0.020*
H1B	0.2387	0.4882	0.4395	0.020*
H2A	0.1437	0.4866	0.2095	0.023*
H2B	0.2408	0.4343	0.2184	0.023*
H3A	0.4806	0.4843	0.3339	0.022*
H3B	0.4124	0.4922	0.1801	0.022*
H4A	0.3511	0.5571	0.3630	0.019*
H4B	0.2774	0.5639	0.2216	0.019*
H51A	0.3468	0.6503	0.2230	0.036*
H51B	0.5251	0.6680	0.2997	0.036*
H51C	0.4122	0.6439	0.3773	0.036*
H52A	0.5684	0.5507	0.1347	0.038*
H52B	0.6084	0.6105	0.1381	0.038*
H52C	0.4277	0.5912	0.0781	0.038*
H6A	0.7474	0.5974	0.3689	0.022*
H6B	0.6882	0.5398	0.3702	0.022*
H7	0.5554	0.5755	0.5338	0.021*
H71A	0.7203	0.6356	0.6742	0.033*
H71B	0.6494	0.6607	0.5334	0.033*
H71C	0.8305	0.6406	0.5798	0.033*
H11	0.0545	0.6086	0.3897	0.032*
H12	0.2374	0.6876	0.5087	0.027*
H13	0.4092	0.7524	0.6167	0.034*
H14	0.5823	0.7377	0.8245	0.037*
H15	0.5825	0.6587	0.9251	0.033*
H16	0.4060	0.5945	0.8200	0.026*
H21	−0.1752	0.5509	0.0532	0.035*
H22	0.1097	0.6328	−0.1239	0.031*
H23	0.1143	0.7076	−0.2418	0.036*
H24	0.0016	0.7826	−0.1918	0.034*
H25	−0.1255	0.7823	−0.0304	0.034*
H26	−0.1362	0.7076	0.0848	0.028*
H1C	−0.172 (3)	0.4660 (11)	0.049 (3)	0.056 (6)*
H1D	−0.174 (4)	0.4737 (11)	0.180 (2)	0.056 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0144 (8)	0.0171 (9)	0.0193 (8)	−0.0002 (7)	0.0059 (7)	0.0008 (6)
C2	0.0195 (10)	0.0214 (11)	0.0164 (9)	0.0011 (8)	0.0050 (8)	0.0015 (8)
C3	0.0196 (10)	0.0189 (11)	0.0186 (10)	0.0024 (8)	0.0080 (8)	0.0014 (8)
N4	0.0129 (8)	0.0190 (9)	0.0169 (8)	0.0006 (7)	0.0053 (6)	0.0022 (7)
C5	0.0167 (9)	0.0203 (11)	0.0193 (10)	−0.0014 (8)	0.0057 (8)	0.0039 (8)
C51	0.0203 (10)	0.0219 (11)	0.0283 (11)	0.0009 (9)	0.0040 (9)	0.0052 (9)
C52	0.0214 (10)	0.0351 (13)	0.0217 (11)	−0.0016 (9)	0.0096 (9)	0.0068 (9)
C6	0.0141 (9)	0.0221 (11)	0.0197 (10)	0.0009 (8)	0.0062 (8)	0.0017 (8)
C7	0.0141 (9)	0.0185 (10)	0.0195 (10)	0.0009 (8)	0.0047 (8)	0.0022 (8)
C71	0.0230 (11)	0.0187 (11)	0.0249 (11)	−0.0010 (8)	0.0083 (9)	0.0011 (8)
P1	0.0134 (2)	0.0193 (3)	0.0151 (2)	0.0001 (2)	0.00502 (19)	0.00021 (19)
O11	0.0161 (7)	0.0328 (9)	0.0150 (7)	0.0046 (6)	0.0053 (6)	0.0021 (6)
O12	0.0165 (7)	0.0186 (7)	0.0194 (7)	0.0003 (6)	0.0080 (5)	−0.0007 (5)
O13	0.0171 (7)	0.0265 (8)	0.0174 (7)	−0.0013 (6)	0.0069 (5)	0.0020 (6)
C11	0.0150 (9)	0.0208 (11)	0.0185 (10)	0.0010 (8)	0.0074 (8)	−0.0021 (8)
C12	0.0225 (10)	0.0217 (11)	0.0236 (11)	0.0025 (9)	0.0073 (9)	0.0022 (8)
C13	0.0289 (12)	0.0202 (12)	0.0362 (13)	−0.0019 (9)	0.0097 (10)	0.0005 (9)
C14	0.0285 (12)	0.0240 (12)	0.0367 (13)	−0.0062 (10)	0.0055 (10)	−0.0061 (10)
C15	0.0238 (11)	0.0311 (13)	0.0242 (11)	−0.0031 (9)	0.0015 (9)	−0.0027 (9)
C16	0.0225 (11)	0.0226 (11)	0.0211 (10)	−0.0001 (9)	0.0064 (8)	0.0011 (8)
P2	0.0186 (3)	0.0210 (3)	0.0147 (3)	0.0024 (2)	0.0045 (2)	0.0014 (2)
O21	0.0189 (7)	0.0244 (8)	0.0264 (8)	0.0011 (6)	0.0067 (6)	0.0066 (6)
O22	0.0185 (7)	0.0238 (8)	0.0208 (7)	0.0048 (6)	0.0044 (6)	0.0022 (6)
O23	0.0434 (10)	0.0301 (9)	0.0161 (7)	0.0058 (7)	0.0098 (7)	0.0012 (6)
C21	0.0172 (10)	0.0218 (11)	0.0164 (9)	−0.0005 (8)	0.0021 (8)	0.0005 (8)
C22	0.0312 (12)	0.0257 (12)	0.0242 (11)	0.0036 (10)	0.0125 (9)	0.0018 (9)
C23	0.0389 (13)	0.0298 (13)	0.0261 (12)	−0.0004 (10)	0.0156 (10)	0.0039 (9)
C24	0.0333 (13)	0.0238 (12)	0.0216 (11)	−0.0050 (10)	0.0001 (9)	0.0037 (9)
C25	0.0315 (12)	0.0197 (12)	0.0293 (12)	0.0026 (9)	0.0035 (10)	−0.0023 (9)
C26	0.0262 (11)	0.0237 (12)	0.0203 (10)	0.0020 (9)	0.0062 (9)	−0.0023 (8)
O1	0.0313 (8)	0.0227 (8)	0.0209 (8)	0.0037 (7)	0.0085 (6)	0.0017 (6)

Geometric parameters (Å, º)

N1—C2	1.499 (2)	C11—C12	1.395 (3)
N1—C7^i	1.512 (2)	C11—C16	1.401 (3)
C2—C3	1.520 (3)	C12—C13	1.388 (3)
C3—N4	1.493 (3)	C13—C14	1.384 (3)
N4—C5	1.519 (2)	C14—C15	1.386 (3)
C5—C51	1.529 (3)	C15—C16	1.388 (3)
C5—C52	1.530 (3)	P2—O23	1.4962 (15)
C5—C6	1.541 (3)	P2—O22	1.5129 (15)
C6—C7	1.543 (3)	P2—O21	1.5774 (15)
C7—N1^i	1.512 (2)	P2—C21	1.798 (2)
C7—C71	1.524 (3)	C21—C22	1.392 (3)
P1—O13	1.5036 (14)	C21—C26	1.393 (3)
P1—O12	1.5204 (14)	C22—C23	1.394 (3)
P1—O11	1.5601 (14)	C23—C24	1.378 (3)
P1—C11	1.803 (2)	C24—C25	1.379 (3)
O11—H11	0.8400	C25—C26	1.387 (3)
C2—N1—C7^i	114.90 (15)	C12—C11—P1	120.90 (15)
N1—C2—C3	113.74 (16)	C16—C11—P1	120.48 (16)
N4—C3—C2	111.57 (16)	C13—C12—C11	120.99 (19)
C3—N4—C5	118.57 (15)	C14—C13—C12	119.7 (2)
N4—C5—C51	104.93 (16)	C13—C14—C15	120.2 (2)
N4—C5—C52	108.40 (16)	C14—C15—C16	120.1 (2)
C51—C5—C52	109.65 (17)	C15—C16—C11	120.3 (2)
N4—C5—C6	111.76 (15)	O23—P2—O22	114.55 (9)
C51—C5—C6	113.27 (17)	O23—P2—O21	111.82 (9)
C52—C5—C6	108.70 (16)	O22—P2—O21	109.44 (8)
C5—C6—C7	117.06 (16)	O23—P2—C21	108.38 (9)
N1^i—C7—C71	108.43 (16)	O22—P2—C21	108.84 (9)
N1^i—C7—C6	108.08 (15)	O21—P2—C21	103.15 (9)
C71—C7—C6	113.90 (17)	C22—C21—C26	118.7 (2)
O13—P1—O12	115.31 (8)	C22—C21—P2	120.77 (16)
O13—P1—O11	108.22 (8)	C26—C21—P2	120.47 (16)
O12—P1—O11	111.30 (8)	C21—C22—C23	120.4 (2)
O13—P1—C11	109.60 (9)	C24—C23—C22	120.1 (2)
O12—P1—C11	106.34 (8)	C23—C24—C25	119.9 (2)
O11—P1—C11	105.63 (9)	C24—C25—C26	120.4 (2)
C12—C11—C16	118.58 (19)	C25—C26—C21	120.5 (2)
C7^i—N1—C2—C3	−73.5 (2)	C12—C13—C14—C15	−0.3 (4)
N1—C2—C3—N4	−78.4 (2)	C13—C14—C15—C16	−0.6 (4)
C2—C3—N4—C5	−176.20 (15)	C14—C15—C16—C11	1.2 (3)
C3—N4—C5—C51	177.24 (16)	C12—C11—C16—C15	−0.8 (3)
C3—N4—C5—C52	60.1 (2)	P1—C11—C16—C15	177.09 (16)
C3—N4—C5—C6	−59.6 (2)	O23—P2—C21—C22	142.68 (17)
N4—C5—C6—C7	−65.2 (2)	O22—P2—C21—C22	17.5 (2)
C51—C5—C6—C7	53.1 (2)	O21—P2—C21—C22	−98.64 (18)
C52—C5—C6—C7	175.19 (17)	O23—P2—C21—C26	−34.19 (19)
C5—C6—C7—N1^i	148.43 (17)	O22—P2—C21—C26	−159.35 (16)
C5—C6—C7—C71	−91.0 (2)	O21—P2—C21—C26	84.49 (18)
O13—P1—C11—C12	−139.96 (16)	C26—C21—C22—C23	0.6 (3)
O12—P1—C11—C12	94.78 (17)	P2—C21—C22—C23	−176.31 (17)
O11—P1—C11—C12	−23.58 (18)	C21—C22—C23—C24	0.8 (3)
O13—P1—C11—C16	42.25 (18)	C22—C23—C24—C25	−1.4 (3)
O12—P1—C11—C16	−83.02 (17)	C23—C24—C25—C26	0.7 (3)
O11—P1—C11—C16	158.62 (16)	C24—C25—C26—C21	0.7 (3)
C16—C11—C12—C13	−0.2 (3)	C22—C21—C26—C25	−1.4 (3)
P1—C11—C12—C13	−178.02 (16)	P2—C21—C26—C25	175.57 (16)
C11—C12—C13—C14	0.7 (3)

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
N1—H1A···O13^ii	0.92	1.85	2.750 (2)	164
N1—H1B···O12	0.92	1.78	2.692 (2)	171
O1—H1C···O22^iii	0.90	1.81	2.707 (2)	169
O1—H1D···O13^ii	0.91	1.83	2.744 (2)	178
N4—H4A···O12	0.92	1.85	2.753 (2)	164
N4—H4B···O22	0.92	1.74	2.637 (2)	163
O11—H11···O23	0.84	1.72	2.496 (2)	152
O21—H21···O1	0.84	1.78	2.616 (2)	171
C2—H2B···O21^iii	0.99	2.55	3.234 (2)	126
C3—H3A···O12^i	0.99	2.48	3.467 (2)	174
C6—H6A···O11^iv	0.99	2.45	3.266 (2)	139
C7—H7···O12	1.00	2.45	3.439 (2)	168

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

(7) Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane- 3,5-dihydroxybenzoic acid (1/2)

Crystal data

C16H38N4^2+·2(C7H5O4^−)	? #Insert any comments here.
Mr = 592.72	Dx = 1.300 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.9162 (13) Å	Cell parameters from 25 reflections
b = 11.8903 (10) Å	θ = 9.6–19.4°
c = 14.5229 (18) Å	µ = 0.09 mm^−1
β = 100.419 (7)°	T = 294 K
V = 1514.3 (3) Å^3	Plate, colourless
Z = 2	0.41 × 0.41 × 0.29 mm
F(000) = 640

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.009
Radiation source: X-ray tube	θmax = 27.4°, θmin = 2.2°
Graphite monochromator	h = −11→11
θ/2θ scans	k = 0→15
3595 measured reflections	l = 0→18
3470 independent reflections	3 standard reflections every 120 min
2576 reflections with I > 2σ(I)	intensity decay: no decay, variation 0.2%

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.2636P] where P = (Fo^2 + 2Fc^2)/3
3470 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. ? #Insert any special details here.

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

	x	y	z	Uiso*/Ueq
O1	0.17725 (12)	0.61562 (9)	0.10997 (7)	0.0393 (3)
O2	0.33606 (12)	0.56332 (10)	0.23823 (8)	0.0509 (3)
O3	−0.19034 (14)	0.28535 (11)	0.05391 (7)	0.0518 (3)
O5	0.02568 (15)	0.27834 (11)	0.37796 (7)	0.0540 (3)
C1	0.21763 (15)	0.55155 (12)	0.17928 (9)	0.0319 (3)
C11	0.11094 (14)	0.45609 (12)	0.19206 (9)	0.0301 (3)
C12	0.00825 (16)	0.41599 (13)	0.11550 (10)	0.0355 (3)
C13	−0.08879 (16)	0.32853 (13)	0.12695 (10)	0.0351 (3)
C14	−0.08607 (16)	0.28071 (13)	0.21394 (10)	0.0361 (3)
C15	0.01691 (17)	0.32110 (13)	0.29050 (9)	0.0350 (3)
C16	0.11514 (16)	0.40886 (12)	0.27973 (10)	0.0331 (3)
N1	0.49503 (13)	0.33192 (9)	0.50291 (8)	0.0286 (2)
C2	0.50602 (17)	0.30885 (12)	0.40487 (10)	0.0340 (3)
C3	0.62426 (17)	0.38170 (12)	0.37278 (11)	0.0371 (3)
C5	0.70088 (15)	0.58758 (12)	0.35190 (9)	0.0307 (3)
N4	0.58177 (12)	0.50317 (9)	0.37138 (7)	0.0270 (2)
C51	0.84959 (17)	0.56789 (14)	0.42040 (12)	0.0453 (4)
C52	0.72246 (19)	0.57140 (14)	0.25080 (10)	0.0421 (4)
C6	0.63498 (17)	0.70457 (12)	0.36406 (10)	0.0342 (3)
C7	0.61803 (16)	0.74121 (12)	0.46240 (10)	0.0344 (3)
C71	0.5768 (2)	0.86617 (14)	0.46170 (15)	0.0602 (5)
H3	−0.1907	0.3242	0.0072	0.078*
H5	−0.0354	0.2265	0.3766	0.081*
H12	0.0049	0.4480	0.0567	0.043*
H14	−0.1522	0.2223	0.2213	0.043*
H16	0.1834	0.4358	0.3311	0.040*
H1A	0.5872	0.3216	0.5391	0.034*
H2A	0.4077	0.3223	0.3653	0.041*
H2B	0.5321	0.2304	0.3985	0.041*
H3A	0.7214	0.3711	0.4143	0.045*
H3B	0.6363	0.3588	0.3104	0.045*
H4E	0.5572	0.5203	0.4272	0.032*
H4A	0.4972	0.5127	0.3277	0.032*
H51A	0.8947	0.4985	0.4053	0.068*
H51B	0.8291	0.5640	0.4830	0.068*
H51C	0.9186	0.6288	0.4160	0.068*
H52A	0.7933	0.6263	0.2359	0.063*
H52B	0.6262	0.5804	0.2095	0.063*
H52C	0.7614	0.4973	0.2435	0.063*
H6A	0.6991	0.7593	0.3403	0.041*
H6B	0.5351	0.7085	0.3245	0.041*
H7	0.7168	0.7312	0.5039	0.041*
H71A	0.4823	0.8784	0.4194	0.090*
H71B	0.6560	0.9094	0.4417	0.090*
H71C	0.5662	0.8891	0.5236	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0463 (6)	0.0389 (6)	0.0317 (5)	−0.0030 (5)	0.0045 (4)	0.0029 (5)
O2	0.0372 (6)	0.0537 (7)	0.0542 (7)	−0.0089 (5)	−0.0120 (5)	0.0059 (6)
O3	0.0547 (7)	0.0661 (8)	0.0296 (6)	−0.0297 (6)	−0.0052 (5)	0.0034 (5)
O5	0.0667 (8)	0.0619 (8)	0.0296 (6)	−0.0247 (6)	−0.0017 (5)	0.0074 (5)
C1	0.0310 (7)	0.0331 (7)	0.0311 (7)	0.0010 (6)	0.0046 (5)	−0.0057 (6)
C11	0.0274 (6)	0.0311 (7)	0.0314 (7)	0.0031 (5)	0.0043 (5)	−0.0025 (6)
C12	0.0369 (7)	0.0412 (8)	0.0271 (7)	−0.0037 (6)	0.0022 (6)	0.0025 (6)
C13	0.0345 (7)	0.0408 (8)	0.0281 (7)	−0.0044 (6)	0.0007 (5)	−0.0035 (6)
C14	0.0382 (8)	0.0379 (8)	0.0317 (7)	−0.0062 (6)	0.0049 (6)	−0.0003 (6)
C15	0.0385 (8)	0.0397 (8)	0.0263 (7)	0.0013 (6)	0.0045 (6)	0.0010 (6)
C16	0.0318 (7)	0.0374 (8)	0.0281 (7)	0.0006 (6)	−0.0004 (5)	−0.0026 (6)
N1	0.0295 (5)	0.0251 (6)	0.0308 (6)	−0.0003 (4)	0.0042 (4)	0.0016 (5)
C2	0.0430 (8)	0.0251 (7)	0.0338 (7)	0.0024 (6)	0.0068 (6)	−0.0028 (6)
C3	0.0453 (8)	0.0289 (7)	0.0400 (8)	0.0073 (6)	0.0157 (7)	0.0023 (6)
C5	0.0297 (7)	0.0319 (7)	0.0305 (7)	−0.0028 (5)	0.0058 (5)	0.0015 (6)
N4	0.0301 (5)	0.0265 (6)	0.0242 (5)	0.0026 (4)	0.0044 (4)	0.0023 (4)
C51	0.0333 (8)	0.0504 (10)	0.0486 (9)	0.0008 (7)	−0.0026 (7)	−0.0048 (8)
C52	0.0489 (9)	0.0454 (9)	0.0349 (8)	−0.0027 (7)	0.0155 (7)	0.0018 (7)
C6	0.0375 (7)	0.0294 (7)	0.0362 (7)	−0.0042 (6)	0.0078 (6)	0.0050 (6)
C7	0.0357 (7)	0.0283 (7)	0.0400 (8)	−0.0052 (6)	0.0089 (6)	−0.0014 (6)
C71	0.0916 (14)	0.0278 (8)	0.0711 (13)	−0.0066 (9)	0.0414 (11)	0.0002 (8)

Geometric parameters (Å, º)

O1—C1	1.2618 (17)	N1—C2	1.4706 (18)
O2—C1	1.2413 (16)	N1—C7^i	1.4865 (17)
O3—C13	1.3643 (16)	C2—C3	1.502 (2)
O5—C15	1.3572 (17)	C3—N4	1.4924 (17)
C1—C11	1.5137 (19)	C5—N4	1.5244 (17)
C11—C16	1.3860 (19)	C5—C51	1.5249 (19)
C11—C12	1.3906 (19)	C5—C52	1.5270 (19)
C12—C13	1.382 (2)	C5—C6	1.533 (2)
C13—C14	1.382 (2)	C6—C7	1.527 (2)
C14—C15	1.393 (2)	C7—N1^i	1.4865 (17)
C15—C16	1.389 (2)	C7—C71	1.530 (2)
O2—C1—O1	124.51 (14)	C2—N1—C7^i	112.77 (11)
O2—C1—C11	118.36 (13)	N1—C2—C3	111.48 (12)
O1—C1—C11	117.10 (12)	N4—C3—C2	111.81 (11)
C16—C11—C12	120.01 (13)	N4—C5—C51	109.31 (11)
C16—C11—C1	120.22 (12)	N4—C5—C52	107.98 (11)
C12—C11—C1	119.77 (12)	C51—C5—C52	111.23 (12)
C13—C12—C11	119.86 (13)	N4—C5—C6	106.36 (10)
O3—C13—C14	117.10 (13)	C51—C5—C6	111.74 (12)
O3—C13—C12	122.11 (13)	C52—C5—C6	110.05 (12)
C14—C13—C12	120.79 (13)	C3—N4—C5	117.13 (10)
C13—C14—C15	119.21 (13)	C7—C6—C5	118.15 (12)
O5—C15—C16	117.12 (12)	N1^i—C7—C6	109.76 (11)
O5—C15—C14	122.41 (14)	N1^i—C7—C71	113.16 (12)
C16—C15—C14	120.47 (13)	C6—C7—C71	109.59 (13)
C11—C16—C15	119.67 (12)
O2—C1—C11—C16	21.9 (2)	O5—C15—C16—C11	−179.79 (13)
O1—C1—C11—C16	−156.36 (13)	C14—C15—C16—C11	−0.3 (2)
O2—C1—C11—C12	−158.22 (14)	C7^i—N1—C2—C3	−178.36 (11)
O1—C1—C11—C12	23.50 (19)	N1—C2—C3—N4	−65.04 (15)
C16—C11—C12—C13	−0.4 (2)	C2—C3—N4—C5	172.57 (11)
C1—C11—C12—C13	179.72 (13)	C51—C5—N4—C3	−53.74 (15)
C11—C12—C13—O3	−179.25 (14)	C52—C5—N4—C3	67.40 (15)
C11—C12—C13—C14	0.5 (2)	C6—C5—N4—C3	−174.52 (11)
O3—C13—C14—C15	179.28 (14)	N4—C5—C6—C7	68.59 (15)
C12—C13—C14—C15	−0.5 (2)	C51—C5—C6—C7	−50.61 (17)
C13—C14—C15—O5	179.85 (14)	C52—C5—C6—C7	−174.69 (12)
C13—C14—C15—C16	0.4 (2)	C5—C6—C7—N1^i	−64.77 (16)
C12—C11—C16—C15	0.3 (2)	C5—C6—C7—C71	170.38 (13)
C1—C11—C16—C15	−179.83 (12)

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
N1—H1A···O3^ii	0.90	2.33	3.100 (2)	143
N4—H4A···O2	0.90	1.85	2.742 (2)	168
N4—H4E···N1^i	0.90	2.12	2.846 (2)	137
O3—H3···O1^iii	0.82	1.87	2.677 (2)	168
O5—H5···O1^iv	0.82	1.86	2.676 (2)	172

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

(8) Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane- 4,4'-biphenol (1/3)

Crystal data

C16H38N4^2+·C12H10O2·2(C12H9O2^−)	? #Insert any comments here.
Mr = 843.09	Dx = 1.227 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.9634 (10) Å	Cell parameters from 25 reflections
b = 18.8981 (19) Å	θ = 10.0–18.4°
c = 12.2344 (11) Å	µ = 0.08 mm^−1
β = 97.725 (7)°	T = 294 K
V = 2282.7 (4) Å^3	Plate, colourless
Z = 2	0.28 × 0.22 × 0.04 mm
F(000) = 908

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.012
Radiation source: X-ray tube	θmax = 25.4°, θmin = 2.1°
Graphite monochromator	h = −12→11
θ/2θ scans	k = 0→22
4427 measured reflections	l = 0→14
4232 independent reflections	3 standard reflections every 120 min
2138 reflections with I > 2σ(I)	intensity decay: no decay, variation .6%

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)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0596P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
4232 reflections	Δρmax = 0.19 e Å^−3
286 parameters	Δρmin = −0.17 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: 0.0055 (8)

Special details

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.2689 (0.0080) x - 2.7804 (0.0228) y + 8.2178 (0.0097) z = 4.8716 (0.0128)

* -0.0018 (0.0018) C11 * 0.0040 (0.0018) C12 * -0.0026 (0.0019) C13 * -0.0010 (0.0020) C14 * 0.0031 (0.0023) C15 * -0.0018 (0.0022) C16 0.0258 (0.0038) O14 0.0161 (0.0048) C11_$1 (label _$1 refers to an atom at (2 - x, 1 - y, -z) 0.0103 (0.0053) C12_$1 0.0170 (0.0052) C13_$1 0.0153 (0.0052) C14_$1 0.0112 (0.0051) C15_$1 0.0161 (0.0057) C16_$1

Rms deviation of fitted atoms = 0.0026

6.2689 (0.0080) x - 2.7804 (0.0228) y + 8.2178 (0.0097) z = 4.8859 (0.0158)

Angle to previous plane (with approximate e.s.d.) = 0.0 (2)

* 0.0018 (0.0018) C11_$1 * -0.0040 (0.0019) C12_$1 * 0.0026 (0.0019) C13_$1 * 0.0010 (0.0020) C14_$1 * -0.0031 (0.0023) C15_$1 * 0.0018 (0.0022) C16_$1 - 0.0258 (0.0038) O14_$1 - 0.0072 (0.0024) Inv1 (Inv1 is a dummy atom at 0, 1/2,0)

Rms deviation of fitted atoms = 0.0026

- 4.4506 (0.0088) x + 15.6967 (0.0110) y + 4.7660 (0.0115) z = 3.9473 (0.0054)

Angle to previous plane (with approximate e.s.d.) = 81.4 (1)

* 0.0155 (0.0016) C21 * -0.0118 (0.0017) C22 * -0.0028 (0.0017) C23 * 0.0138 (0.0018) C24 * -0.0100 (0.0019) C25 * -0.0046 (0.0019) C26 0.0725 (0.0036) O24 0.1354 (0.0037) C31 0.5005 (0.0062) C34 0.7095 (0.0071) O34

Rms deviation of fitted atoms = 0.0108

- 1.5384 (0.0093) x + 18.4407 (0.0046) y - 1.6236 (0.0127) z = 4.2357 (0.0020)

Angle to previous plane (with approximate e.s.d.) = 34.1 (1)

* 0.0028 (0.0017) C31 * 0.0006 (0.0017) C32 * -0.0027 (0.0018) C33 * 0.0013 (0.0018) C34 * 0.0022 (0.0018) C35 * -0.0042 (0.0018) C36 0.0020 (0.0035) O34 0.0658 (0.0038) C21 0.3644 (0.0060) C24 0.5523 (0.0070) O24

Rms deviation of fitted atoms = 0.0026

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

	x	y	z	Uiso*/Ueq
C11	0.9475 (2)	0.49370 (13)	0.03683 (19)	0.0360 (6)
C12	0.8967 (3)	0.42730 (14)	0.0538 (2)	0.0459 (7)
C13	0.8001 (3)	0.41508 (14)	0.1225 (2)	0.0458 (7)
C14	0.7503 (3)	0.46944 (14)	0.1791 (2)	0.0426 (6)
O14	0.65757 (19)	0.45884 (9)	0.24956 (17)	0.0571 (6)
C15	0.7997 (3)	0.53630 (15)	0.1645 (3)	0.0682 (10)
C16	0.8955 (3)	0.54783 (15)	0.0948 (3)	0.0631 (9)
C21	0.2177 (2)	0.26553 (12)	0.1602 (2)	0.0342 (6)
C22	0.2739 (2)	0.24735 (12)	0.2668 (2)	0.0364 (6)
C23	0.4012 (2)	0.27002 (12)	0.31299 (19)	0.0355 (6)
C24	0.4809 (2)	0.31186 (13)	0.2531 (2)	0.0389 (6)
O24	0.60170 (16)	0.33611 (9)	0.29835 (14)	0.0499 (5)
C25	0.4273 (3)	0.32807 (15)	0.1447 (2)	0.0483 (7)
C26	0.2993 (2)	0.30557 (14)	0.1004 (2)	0.0442 (7)
C31	0.0759 (2)	0.24639 (12)	0.1160 (2)	0.0349 (6)
C32	0.0341 (2)	0.23306 (13)	0.0055 (2)	0.0399 (6)
C33	−0.0997 (2)	0.21826 (13)	−0.0337 (2)	0.0408 (7)
C34	−0.1970 (2)	0.21651 (12)	0.0362 (2)	0.0371 (6)
O34	−0.32973 (16)	0.20249 (11)	0.00226 (14)	0.0516 (5)
C35	−0.1577 (2)	0.22958 (13)	0.1468 (2)	0.0426 (7)
C36	−0.0240 (2)	0.24381 (14)	0.1858 (2)	0.0412 (6)
N1	0.49383 (19)	0.54981 (11)	0.34583 (16)	0.0395 (5)
C2	0.5724 (3)	0.61183 (14)	0.3922 (2)	0.0479 (7)
C3	0.6971 (3)	0.58896 (15)	0.4669 (2)	0.0521 (8)
N4	0.66320 (19)	0.55448 (11)	0.56589 (17)	0.0402 (5)
C5	0.7799 (2)	0.52234 (14)	0.6384 (2)	0.0417 (6)
C51	0.8924 (3)	0.57641 (15)	0.6736 (3)	0.0644 (9)
C52	0.8376 (3)	0.46191 (15)	0.5765 (3)	0.0648 (9)
C6	0.7265 (3)	0.49519 (15)	0.7422 (2)	0.0539 (8)
C7	0.6320 (3)	0.43188 (15)	0.7314 (2)	0.0536 (8)
C71	0.5940 (4)	0.4073 (2)	0.8406 (3)	0.0988 (14)
H12	0.9290	0.3890	0.0173	0.055*
H13	0.7685	0.3693	0.1305	0.055*
H14	0.6493	0.4163	0.2600	0.086*
H15	0.7682	0.5742	0.2022	0.082*
H16	0.9263	0.5937	0.0864	0.076*
H22	0.2241	0.2189	0.3087	0.044*
H23	0.4341	0.2572	0.3850	0.043*
H25	0.4786	0.3545	0.1013	0.058*
H26	0.2668	0.3177	0.0280	0.053*
H32	0.0976	0.2341	−0.0437	0.048*
H33	−0.1243	0.2094	−0.1085	0.049*
H34	−0.3400	0.1925	−0.0636	0.077*
H35	−0.2218	0.2288	0.1954	0.051*
H36	0.0002	0.2519	0.2608	0.049*
H1A	0.5475	0.5228	0.3094	0.047*
H1E	0.4700	0.5238	0.4018	0.047*
H2A	0.5162	0.6407	0.4334	0.057*
H2B	0.5985	0.6403	0.3326	0.057*
H3A	0.7488	0.5566	0.4274	0.062*
H3B	0.7533	0.6300	0.4876	0.062*
H4A	0.6235	0.5865	0.6056	0.048*
H51A	0.8560	0.6153	0.7107	0.097*
H51B	0.9282	0.5936	0.6095	0.097*
H51C	0.9635	0.5542	0.7225	0.097*
H52A	0.8848	0.4809	0.5197	0.097*
H52B	0.7651	0.4321	0.5438	0.097*
H52C	0.8992	0.4347	0.6270	0.097*
H6A	0.8040	0.4833	0.7959	0.065*
H6B	0.6797	0.5340	0.7727	0.065*
H7	0.6778	0.3928	0.6989	0.064*
H71A	0.5273	0.3705	0.8281	0.148*
H71B	0.5576	0.4463	0.8773	0.148*
H71C	0.6730	0.3894	0.8857	0.148*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0320 (14)	0.0380 (15)	0.0377 (15)	0.0017 (11)	0.0036 (11)	0.0056 (12)
C12	0.0467 (16)	0.0431 (16)	0.0509 (18)	−0.0031 (13)	0.0180 (14)	−0.0067 (13)
C13	0.0484 (16)	0.0375 (15)	0.0537 (18)	−0.0083 (13)	0.0146 (14)	−0.0046 (13)
C14	0.0406 (15)	0.0461 (16)	0.0433 (17)	−0.0021 (12)	0.0134 (13)	0.0015 (14)
O14	0.0606 (12)	0.0470 (12)	0.0710 (14)	−0.0066 (10)	0.0353 (11)	−0.0020 (11)
C15	0.077 (2)	0.0387 (18)	0.101 (3)	0.0021 (15)	0.056 (2)	−0.0001 (17)
C16	0.069 (2)	0.0362 (16)	0.093 (3)	0.0024 (15)	0.0436 (19)	0.0098 (16)
C21	0.0325 (13)	0.0370 (14)	0.0336 (14)	0.0022 (11)	0.0060 (11)	−0.0047 (12)
C22	0.0375 (14)	0.0376 (14)	0.0355 (15)	−0.0017 (12)	0.0099 (12)	−0.0001 (12)
C23	0.0368 (14)	0.0403 (15)	0.0288 (14)	−0.0002 (11)	0.0018 (11)	0.0014 (11)
C24	0.0350 (15)	0.0437 (15)	0.0377 (15)	−0.0022 (12)	0.0038 (12)	0.0020 (12)
O24	0.0371 (10)	0.0636 (13)	0.0464 (11)	−0.0151 (9)	−0.0040 (9)	0.0096 (9)
C25	0.0432 (16)	0.0636 (19)	0.0383 (17)	−0.0134 (14)	0.0058 (13)	0.0101 (14)
C26	0.0395 (15)	0.0580 (17)	0.0336 (15)	−0.0057 (13)	−0.0003 (13)	0.0068 (13)
C31	0.0347 (13)	0.0350 (14)	0.0355 (15)	0.0027 (11)	0.0062 (12)	−0.0043 (11)
C32	0.0323 (14)	0.0580 (18)	0.0308 (15)	−0.0010 (12)	0.0093 (12)	−0.0009 (12)
C33	0.0359 (15)	0.0524 (16)	0.0332 (15)	−0.0023 (12)	0.0009 (12)	−0.0015 (12)
C34	0.0277 (14)	0.0405 (15)	0.0421 (16)	0.0006 (11)	0.0009 (12)	−0.0018 (12)
O34	0.0322 (10)	0.0787 (14)	0.0435 (11)	−0.0051 (9)	0.0035 (9)	−0.0070 (11)
C35	0.0348 (14)	0.0545 (17)	0.0413 (16)	−0.0069 (12)	0.0147 (12)	−0.0083 (13)
C36	0.0387 (15)	0.0534 (16)	0.0319 (14)	−0.0034 (12)	0.0061 (12)	−0.0122 (12)
N1	0.0328 (11)	0.0486 (13)	0.0377 (13)	−0.0028 (10)	0.0073 (10)	0.0038 (10)
C2	0.0479 (17)	0.0475 (17)	0.0485 (18)	−0.0089 (13)	0.0072 (13)	0.0031 (14)
C3	0.0401 (16)	0.0655 (19)	0.0504 (18)	−0.0175 (14)	0.0057 (14)	0.0059 (15)
N4	0.0357 (12)	0.0475 (13)	0.0378 (13)	−0.0017 (10)	0.0064 (10)	0.0002 (10)
C5	0.0310 (14)	0.0457 (16)	0.0477 (17)	−0.0033 (12)	0.0025 (12)	0.0010 (13)
C51	0.0509 (18)	0.060 (2)	0.076 (2)	−0.0136 (15)	−0.0120 (16)	0.0105 (17)
C52	0.0554 (19)	0.057 (2)	0.085 (2)	0.0043 (15)	0.0211 (17)	−0.0015 (18)
C6	0.0401 (16)	0.069 (2)	0.0494 (18)	−0.0064 (14)	−0.0067 (13)	0.0086 (15)
C7	0.0364 (15)	0.0644 (19)	0.0567 (19)	−0.0037 (14)	−0.0060 (14)	0.0223 (15)
C71	0.081 (3)	0.143 (4)	0.066 (2)	−0.043 (2)	−0.016 (2)	0.049 (2)

Geometric parameters (Å, º)

C11—C12	1.379 (3)	C31—C36	1.397 (3)
C11—C16	1.384 (4)	C32—C33	1.383 (3)
C11—C11^i	1.489 (5)	C33—C34	1.377 (3)
C12—C13	1.380 (3)	C34—O34	1.358 (3)
C13—C14	1.369 (3)	C34—C35	1.379 (3)
C14—O14	1.360 (3)	C35—C36	1.379 (3)
C14—C15	1.376 (4)	N1—C2	1.479 (3)
C15—C16	1.380 (4)	N1—C7^ii	1.505 (3)
C21—C26	1.389 (3)	C2—C3	1.503 (3)
C21—C22	1.391 (3)	C3—N4	1.455 (3)
C21—C31	1.488 (3)	N4—C5	1.494 (3)
C22—C23	1.386 (3)	C5—C52	1.525 (4)
C23—C24	1.396 (3)	C5—C6	1.530 (4)
C24—O24	1.337 (3)	C5—C51	1.535 (3)
C24—C25	1.396 (3)	C6—C7	1.517 (3)
C25—C26	1.383 (3)	C7—N1^ii	1.505 (3)
C31—C32	1.383 (3)	C7—C71	1.510 (4)
C12—C11—C16	115.2 (2)	C36—C31—C21	120.4 (2)
C12—C11—C11^i	122.6 (3)	C33—C32—C31	121.7 (2)
C16—C11—C11^i	122.2 (3)	C34—C33—C32	121.0 (2)
C13—C12—C11	123.0 (2)	O34—C34—C33	123.6 (2)
C14—C13—C12	120.8 (2)	O34—C34—C35	118.1 (2)
O14—C14—C13	122.2 (2)	C33—C34—C35	118.3 (2)
O14—C14—C15	120.2 (2)	C36—C35—C34	120.6 (2)
C13—C14—C15	117.6 (2)	C35—C36—C31	122.0 (2)
C14—C15—C16	121.0 (3)	C2—N1—C7^ii	114.3 (2)
C15—C16—C11	122.5 (3)	N1—C2—C3	110.9 (2)
C26—C21—C22	116.0 (2)	N4—C3—C2	111.7 (2)
C26—C21—C31	122.4 (2)	C3—N4—C5	115.3 (2)
C22—C21—C31	121.6 (2)	N4—C5—C52	108.9 (2)
C23—C22—C21	122.4 (2)	N4—C5—C6	107.4 (2)
C22—C23—C24	121.0 (2)	C52—C5—C6	111.0 (2)
O24—C24—C23	121.4 (2)	N4—C5—C51	112.1 (2)
O24—C24—C25	121.8 (2)	C52—C5—C51	109.1 (2)
C23—C24—C25	116.8 (2)	C6—C5—C51	108.2 (2)
C26—C25—C24	121.3 (2)	C7—C6—C5	118.2 (2)
C25—C26—C21	122.4 (2)	N1^ii—C7—C71	109.8 (2)
C32—C31—C36	116.4 (2)	N1^ii—C7—C6	109.2 (2)
C32—C31—C21	123.1 (2)	C71—C7—C6	113.1 (3)
C16—C11—C12—C13	0.6 (4)	C22—C21—C31—C36	33.0 (3)
C11^i—C11—C12—C13	179.5 (3)	C36—C31—C32—C33	0.3 (4)
C11—C12—C13—C14	−0.7 (4)	C21—C31—C32—C33	−177.3 (2)
C12—C13—C14—O14	−178.3 (2)	C31—C32—C33—C34	0.3 (4)
C12—C13—C14—C15	0.2 (4)	C32—C33—C34—O34	179.8 (2)
O14—C14—C15—C16	178.9 (3)	C32—C33—C34—C35	−0.3 (4)
C13—C14—C15—C16	0.3 (5)	O34—C34—C35—C36	179.7 (2)
C14—C15—C16—C11	−0.4 (5)	C33—C34—C35—C36	−0.2 (4)
C12—C11—C16—C15	0.0 (4)	C34—C35—C36—C31	0.7 (4)
C11^i—C11—C16—C15	−178.9 (3)	C32—C31—C36—C35	−0.7 (4)
C26—C21—C22—C23	2.6 (3)	C21—C31—C36—C35	176.9 (2)
C31—C21—C22—C23	−174.1 (2)	C7^ii—N1—C2—C3	−179.2 (2)
C21—C22—C23—C24	−1.0 (4)	N1—C2—C3—N4	−67.1 (3)
C22—C23—C24—O24	177.5 (2)	C2—C3—N4—C5	173.0 (2)
C22—C23—C24—C25	−1.4 (4)	C3—N4—C5—C52	−64.9 (3)
O24—C24—C25—C26	−176.8 (2)	C3—N4—C5—C6	174.8 (2)
C23—C24—C25—C26	2.1 (4)	C3—N4—C5—C51	56.0 (3)
C24—C25—C26—C21	−0.4 (4)	N4—C5—C6—C7	69.3 (3)
C22—C21—C26—C25	−1.9 (4)	C52—C5—C6—C7	−49.7 (3)
C31—C21—C26—C25	174.8 (2)	C51—C5—C6—C7	−169.4 (2)
C26—C21—C31—C32	33.9 (4)	C5—C6—C7—N1^ii	−61.3 (3)
C22—C21—C31—C32	−149.6 (2)	C5—C6—C7—C71	176.1 (3)
C26—C21—C31—C36	−143.6 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O14	0.90	1.85	2.742 (3)	172
N1—H1E···N4^ii	0.90	2.06	2.820 (3)	141
O14—H14···O24	0.82	1.67	2.477 (2)	166
O34—H34···O24^iii	0.82	1.79	2.601 (2)	167

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