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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 R_4^2(8) and R_6^6(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\overline 1) sheets of R_8^6(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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768103026739/na5008sup1.cif
Contains datablocks global, I, II, III, IV

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103026739/na5008Isup2.fcf
Contains datablock I

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103026739/na5008IIsup3.fcf
Contains datablock 71

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103026739/na5008IIIsup4.fcf
Contains datablock 53

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103026739/na5008IVsup5.fcf
Contains datablock 65

CCDC references: 230841; 230842; 230843; 230844

Comment top

In full text version

Experimental top

In full text version

Refinement top

In full text version

Computing details top

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 top
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In full text version
(I) Cyclam/adamantane-1-carboxylic acid/water (1/2/4) top
Crystal data top
C10H26N4·2(C11H15O2)·4(H2O)F(000) = 696
Mr = 632.87Dx = 1.254 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3796 reflections
a = 8.8604 (2) Åθ = 2.9–27.5°
b = 6.8025 (1) ŵ = 0.09 mm1
c = 27.8239 (6) ÅT = 150 K
β = 91.044 (1)°Block, colourless
V = 1676.75 (6) Å30.35 × 0.25 × 0.22 mm
Z = 2
Data collection top
Kappa-CCD
diffractometer
2910 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.035
Graphite monochromatorθmax = 27.5°, θmin = 2.9°
ϕ scans, and ω scans with κ offsetsh = 011
10461 measured reflectionsk = 08
3796 independent reflectionsl = 3636
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0475P)2 + 0.6247P]
where P = (Fo2 + 2Fc2)/3
3796 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C10H26N4·2(C11H15O2)·4(H2O)V = 1676.75 (6) Å3
Mr = 632.87Z = 2
Monoclinic, P21/nMo Kα radiation
a = 8.8604 (2) ŵ = 0.09 mm1
b = 6.8025 (1) ÅT = 150 K
c = 27.8239 (6) Å0.35 × 0.25 × 0.22 mm
β = 91.044 (1)°
Data collection top
Kappa-CCD
diffractometer
2910 reflections with I > 2σ(I)
10461 measured reflectionsRint = 0.035
3796 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.05Δρmax = 0.28 e Å3
3796 reflectionsΔρmin = 0.22 e Å3
199 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.81889 (13)0.06955 (18)0.45866 (4)0.0301 (3)
N140.86805 (14)0.10443 (18)0.55534 (4)0.0296 (3)
C120.70545 (16)0.0458 (2)0.48525 (6)0.0335 (3)
C130.72543 (16)0.0187 (2)0.53916 (5)0.0332 (3)
C150.90131 (17)0.0665 (2)0.60637 (5)0.0329 (3)
C161.05839 (17)0.1420 (2)0.61920 (5)0.0344 (3)
C171.18354 (17)0.0317 (2)0.59407 (5)0.0321 (3)
O10.60518 (13)0.48842 (19)0.56160 (4)0.0417 (3)
O20.82011 (12)0.54080 (18)0.60192 (4)0.0402 (3)
C10.59123 (15)0.5408 (2)0.64657 (5)0.0231 (3)
C20.69536 (16)0.5546 (2)0.69106 (5)0.0288 (3)
C30.49453 (16)0.7287 (2)0.64317 (5)0.0269 (3)
C40.48522 (16)0.3639 (2)0.65230 (5)0.0268 (3)
C50.39152 (16)0.3865 (2)0.69765 (5)0.0289 (3)
C60.49681 (17)0.4000 (2)0.74184 (5)0.0317 (3)
C70.60149 (16)0.5779 (2)0.73651 (5)0.0302 (3)
C80.50682 (17)0.7659 (2)0.73270 (5)0.0325 (3)
C90.40094 (16)0.7521 (2)0.68864 (5)0.0295 (3)
C100.29635 (16)0.5743 (2)0.69374 (5)0.0323 (3)
C110.68036 (16)0.5210 (2)0.59995 (5)0.0277 (3)
O30.31055 (13)0.43994 (16)0.52907 (4)0.0371 (3)
O40.01236 (13)0.6691 (2)0.53519 (4)0.0497 (3)
H11A0.80190.20120.46380.036*
H11B0.91350.04030.47090.036*
H140.86510.23800.55030.036*
H12A0.60280.00320.47520.040*
H12B0.71590.18680.47720.040*
H13A0.64100.08280.55590.040*
H13B0.72400.12320.54710.040*
H15A0.89570.07640.61280.039*
H15B0.82580.13350.62640.039*
H16A1.06440.28290.61060.041*
H16B1.07470.13100.65440.041*
H17A1.28240.07280.60790.039*
H17B1.17190.11100.59990.039*
H2A0.76390.66870.68790.035*
H2B0.75790.43430.69370.035*
H3A0.56090.84460.63940.032*
H3B0.42640.72110.61460.032*
H4A0.41710.35410.62380.032*
H4B0.54540.24150.65440.032*
H50.32340.27020.70090.035*
H6A0.55760.27830.74480.038*
H6B0.43650.41420.77120.038*
H70.67060.58660.76530.036*
H8A0.57400.88130.72960.039*
H8B0.44700.78250.76210.039*
H90.33900.87460.68610.035*
H10A0.22730.56580.66540.039*
H10B0.23460.58930.72280.039*
H310.33090.45910.49600.056*
H320.40680.44900.54450.056*
H410.08140.57820.53530.075*
H420.04470.61600.55670.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0295 (6)0.0308 (7)0.0300 (6)0.0007 (5)0.0012 (5)0.0012 (5)
N140.0339 (6)0.0267 (6)0.0282 (6)0.0010 (5)0.0025 (5)0.0007 (5)
C120.0255 (7)0.0349 (8)0.0402 (8)0.0007 (6)0.0035 (6)0.0019 (7)
C130.0304 (7)0.0336 (8)0.0358 (8)0.0017 (6)0.0069 (6)0.0022 (7)
C150.0384 (8)0.0328 (8)0.0276 (7)0.0000 (7)0.0071 (6)0.0002 (6)
C160.0434 (9)0.0347 (8)0.0252 (7)0.0026 (7)0.0008 (6)0.0008 (6)
C170.0350 (8)0.0330 (8)0.0282 (7)0.0034 (7)0.0035 (6)0.0019 (6)
O10.0465 (6)0.0566 (8)0.0223 (5)0.0091 (6)0.0075 (5)0.0043 (5)
O20.0318 (6)0.0525 (7)0.0366 (6)0.0046 (5)0.0117 (5)0.0052 (5)
C10.0252 (6)0.0230 (7)0.0211 (6)0.0005 (5)0.0027 (5)0.0002 (5)
C20.0260 (7)0.0343 (8)0.0261 (7)0.0002 (6)0.0007 (5)0.0002 (6)
C30.0320 (7)0.0239 (7)0.0249 (6)0.0020 (6)0.0022 (5)0.0016 (5)
C40.0332 (7)0.0235 (7)0.0238 (6)0.0015 (6)0.0043 (6)0.0017 (6)
C50.0321 (7)0.0292 (7)0.0258 (7)0.0071 (6)0.0066 (6)0.0004 (6)
C60.0405 (8)0.0319 (8)0.0228 (7)0.0018 (7)0.0064 (6)0.0040 (6)
C70.0315 (7)0.0380 (8)0.0211 (6)0.0004 (6)0.0014 (6)0.0014 (6)
C80.0385 (8)0.0310 (8)0.0281 (7)0.0031 (6)0.0060 (6)0.0076 (6)
C90.0316 (7)0.0275 (7)0.0295 (7)0.0067 (6)0.0041 (6)0.0011 (6)
C100.0269 (7)0.0406 (9)0.0296 (7)0.0004 (6)0.0056 (6)0.0031 (6)
C110.0340 (7)0.0232 (7)0.0263 (7)0.0010 (6)0.0081 (6)0.0022 (6)
O30.0430 (6)0.0394 (6)0.0290 (5)0.0100 (5)0.0051 (4)0.0007 (5)
O40.0463 (7)0.0526 (8)0.0509 (7)0.0028 (6)0.0179 (6)0.0089 (6)
Geometric parameters (Å, º) top
N11—C121.4835 (19)C2—H2A0.99
N11—C17i1.4892 (18)C2—H2B0.99
N11—H11A0.92C3—C91.5334 (19)
N11—H11B0.92C3—H3A0.99
N14—C131.4558 (19)C3—H3B0.99
N14—C151.4676 (18)C4—C51.5308 (18)
N14—H140.92C4—H4A0.99
C12—C131.518 (2)C4—H4B0.99
C12—H12A0.99C5—C61.533 (2)
C12—H12B0.99C5—C101.534 (2)
C13—H13A0.99C5—H51.00
C13—H13B0.99C6—C71.534 (2)
C15—C161.520 (2)C6—H6A0.99
C15—H15A0.99C6—H6B0.99
C15—H15B0.99C7—C81.532 (2)
C16—C171.520 (2)C7—H71.00
C16—H16A0.99C8—C91.533 (2)
C16—H16B0.99C8—H8A0.99
C17—N11i1.4892 (18)C8—H8B0.99
C17—H17A0.99C9—C101.532 (2)
C17—H17B0.99C9—H91.00
O1—C111.2670 (18)C10—H10A0.99
O2—C111.2458 (18)C10—H10B0.99
C1—C21.5332 (19)O3—H310.95
C1—C41.5366 (19)O3—H320.95
C1—C111.5369 (18)O4—H410.87
C1—C31.5410 (19)O4—H420.87
C2—C71.5344 (19)
C12—N11—C17i113.71 (12)C9—C3—H3A109.6
C12—N11—H11A108.8C1—C3—H3A109.6
C17i—N11—H11A108.8C9—C3—H3B109.6
C12—N11—H11B108.8C1—C3—H3B109.6
C17i—N11—H11B108.8H3A—C3—H3B108.2
H11A—N11—H11B107.7C5—C4—C1110.41 (11)
C13—N14—C15112.75 (12)C5—C4—H4A109.6
C13—N14—H14109.0C1—C4—H4A109.6
C15—N14—H14109.0C5—C4—H4B109.6
N11—C12—C13111.13 (12)C1—C4—H4B109.6
N11—C12—H12A109.4H4A—C4—H4B108.1
C13—C12—H12A109.4C4—C5—C6109.63 (12)
N11—C12—H12B109.4C4—C5—C10109.31 (11)
C13—C12—H12B109.4C6—C5—C10109.44 (12)
H12A—C12—H12B108.0C4—C5—H5109.5
N14—C13—C12109.98 (12)C6—C5—H5109.5
N14—C13—H13A109.7C10—C5—H5109.5
C12—C13—H13A109.7C5—C6—C7109.27 (11)
N14—C13—H13B109.7C5—C6—H6A109.8
C12—C13—H13B109.7C7—C6—H6A109.8
H13A—C13—H13B108.2C5—C6—H6B109.8
N14—C15—C16109.57 (12)C7—C6—H6B109.8
N14—C15—H15A109.8H6A—C6—H6B108.3
C16—C15—H15A109.8C8—C7—C6109.52 (12)
N14—C15—H15B109.8C8—C7—C2109.48 (12)
C16—C15—H15B109.8C6—C7—C2109.63 (12)
H15A—C15—H15B108.2C8—C7—H7109.4
C17—C16—C15113.45 (13)C6—C7—H7109.4
C17—C16—H16A108.9C2—C7—H7109.4
C15—C16—H16A108.9C7—C8—C9109.31 (11)
C17—C16—H16B108.9C7—C8—H8A109.8
C15—C16—H16B108.9C9—C8—H8A109.8
H16A—C16—H16B107.7C7—C8—H8B109.8
N11i—C17—C16111.74 (12)C9—C8—H8B109.8
N11i—C17—H17A109.3H8A—C8—H8B108.3
C16—C17—H17A109.3C10—C9—C8109.67 (12)
N11i—C17—H17B109.3C10—C9—C3109.39 (12)
C16—C17—H17B109.3C8—C9—C3109.50 (11)
H17A—C17—H17B107.9C10—C9—H9109.4
C2—C1—C4108.92 (11)C8—C9—H9109.4
C2—C1—C11112.08 (11)C3—C9—H9109.4
C4—C1—C11110.07 (11)C9—C10—C5109.36 (11)
C2—C1—C3108.93 (11)C9—C10—H10A109.8
C4—C1—C3108.41 (11)C5—C10—H10A109.8
C11—C1—C3108.35 (11)C9—C10—H10B109.8
C1—C2—C7110.15 (11)C5—C10—H10B109.8
C1—C2—H2A109.6H10A—C10—H10B108.3
C7—C2—H2A109.6O2—C11—O1124.24 (13)
C1—C2—H2B109.6O2—C11—C1118.63 (12)
C7—C2—H2B109.6O1—C11—C1117.12 (12)
H2A—C2—H2B108.1H31—O3—H32104.1
C9—C3—C1110.10 (11)H41—O4—H4296.9
C17i—N11—C12—C13173.49 (12)C5—C6—C7—C259.81 (15)
C15—N14—C13—C12174.43 (12)C1—C2—C7—C860.16 (15)
N11—C12—C13—N1466.53 (16)C1—C2—C7—C660.00 (15)
C13—N14—C15—C16174.22 (13)C6—C7—C8—C960.07 (15)
N14—C15—C16—C1765.65 (17)C2—C7—C8—C960.16 (15)
C15—C16—C17—N11i68.14 (17)C7—C8—C9—C1059.93 (15)
C4—C1—C2—C758.97 (15)C7—C8—C9—C360.11 (15)
C11—C1—C2—C7178.99 (12)C1—C3—C9—C1060.36 (14)
C3—C1—C2—C759.11 (15)C1—C3—C9—C859.86 (15)
C2—C1—C3—C959.01 (14)C8—C9—C10—C559.94 (15)
C4—C1—C3—C959.39 (14)C3—C9—C10—C560.17 (15)
C11—C1—C3—C9178.82 (11)C4—C5—C10—C960.00 (15)
C2—C1—C4—C558.94 (14)C6—C5—C10—C960.08 (14)
C11—C1—C4—C5177.80 (11)C2—C1—C11—O28.16 (18)
C3—C1—C4—C559.46 (14)C4—C1—C11—O2129.54 (14)
C1—C4—C5—C659.71 (15)C3—C1—C11—O2112.07 (14)
C1—C4—C5—C1060.26 (15)C2—C1—C11—O1173.02 (13)
C4—C5—C6—C759.63 (15)C4—C1—C11—O151.63 (16)
C10—C5—C6—C760.25 (15)C3—C1—C11—O166.75 (16)
C5—C6—C7—C860.32 (15)
Symmetry code: (i) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H31···O1ii0.951.752.689 (2)171
O3—H32···O10.951.832.767 (2)168
O4—H41···O30.872.253.075 (2)159
O4—H42···O2iii0.871.832.688 (2)171
N11—H11A···O3iv0.921.922.792 (2)158
N11—H11B···N14i0.922.132.818 (2)131
N14—H14···O20.922.553.270 (2)136
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y+1, z+1; (iii) x1, y, z; (iv) x+1, y, z+1.
(II) Cyclam/4-aminobenzoic acid/water (1/2/1) top
Crystal data top
C10H26N4·2(C7H6NO2)·H2OF(000) = 1064
Mr = 492.62Dx = 1.215 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3016 reflections
a = 19.6462 (8) Åθ = 2.7–27.3°
b = 9.0374 (4) ŵ = 0.09 mm1
c = 15.2051 (7) ÅT = 150 K
β = 94.127 (2)°Plate, colourless
V = 2692.7 (2) Å30.32 × 0.29 × 0.14 mm
Z = 4
Data collection top
Kappa-CCD
diffractometer
2156 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.046
Graphite monochromatorθmax = 27.3°, θmin = 2.7°
ϕ scans, and ω scans with κ offsetsh = 025
12532 measured reflectionsk = 011
3016 independent reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0325P)2 + 1.3517P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3016 reflectionsΔρmax = 0.20 e Å3
160 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0053 (11)
Crystal data top
C10H26N4·2(C7H6NO2)·H2OV = 2692.7 (2) Å3
Mr = 492.62Z = 4
Monoclinic, C2/cMo Kα radiation
a = 19.6462 (8) ŵ = 0.09 mm1
b = 9.0374 (4) ÅT = 150 K
c = 15.2051 (7) Å0.32 × 0.29 × 0.14 mm
β = 94.127 (2)°
Data collection top
Kappa-CCD
diffractometer
2156 reflections with I > 2σ(I)
12532 measured reflectionsRint = 0.046
3016 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.07Δρmax = 0.20 e Å3
3016 reflectionsΔρmin = 0.19 e Å3
160 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.42773 (7)0.62905 (15)0.55994 (8)0.0398 (3)
C20.38060 (8)0.5088 (2)0.58261 (11)0.0448 (4)
C30.37065 (8)0.4001 (2)0.50743 (12)0.0473 (4)
N40.43578 (7)0.33453 (15)0.48770 (9)0.0425 (3)
C50.42828 (9)0.2312 (2)0.41292 (12)0.0517 (5)
C60.49585 (9)0.1631 (2)0.39323 (12)0.0502 (4)
C70.54826 (9)0.27379 (19)0.36504 (11)0.0457 (4)
O10.45163 (6)0.76226 (14)0.36951 (7)0.0469 (3)
O20.35882 (6)0.80238 (13)0.44065 (7)0.0451 (3)
N140.26661 (7)1.10796 (17)0.07289 (9)0.0504 (4)
C110.35859 (7)0.88730 (17)0.29302 (10)0.0345 (3)
C120.38777 (8)0.88507 (16)0.21238 (10)0.0357 (4)
C130.35641 (8)0.95465 (17)0.13929 (10)0.0378 (4)
C140.29559 (8)1.03384 (18)0.14536 (10)0.0388 (4)
C150.26634 (8)1.0356 (2)0.22606 (11)0.0479 (4)
C160.29729 (8)0.9625 (2)0.29786 (11)0.0453 (4)
C170.39247 (8)0.81222 (17)0.37225 (10)0.0366 (4)
O30.50000.56935 (18)0.25000.0516 (5)
H1A0.40610.68680.51670.048*
H1B0.46520.58720.53680.048*
H2A0.33600.55170.59540.054*
H2B0.39960.45680.63620.054*
H3A0.33890.32110.52330.057*
H3B0.35010.45150.45440.057*
H40.45410.28500.53670.051*
H5A0.40890.28460.36010.062*
H5B0.39600.15170.42650.062*
H6A0.48760.08870.34590.060*
H6B0.51500.11060.44650.060*
H7A0.58760.22010.34330.055*
H7B0.52770.33530.31620.055*
H14A0.22861.15820.07690.060*
H14B0.28611.10510.02260.060*
H120.42990.83500.20740.043*
H130.37630.94870.08430.045*
H150.22481.08750.23170.057*
H160.27610.96370.35210.054*
H30.47870.63170.29020.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0416 (7)0.0398 (7)0.0375 (7)0.0026 (6)0.0011 (5)0.0056 (6)
C20.0396 (9)0.0470 (10)0.0478 (9)0.0000 (7)0.0035 (7)0.0099 (8)
C30.0395 (9)0.0472 (10)0.0539 (10)0.0022 (8)0.0056 (7)0.0072 (8)
N40.0412 (7)0.0413 (8)0.0434 (7)0.0012 (6)0.0073 (6)0.0047 (6)
C50.0519 (10)0.0480 (10)0.0533 (10)0.0045 (8)0.0092 (8)0.0035 (8)
C60.0579 (11)0.0424 (10)0.0488 (10)0.0000 (8)0.0055 (8)0.0023 (8)
C70.0588 (11)0.0390 (9)0.0386 (9)0.0071 (8)0.0019 (7)0.0016 (7)
O10.0414 (6)0.0611 (8)0.0379 (6)0.0108 (6)0.0002 (5)0.0088 (5)
O20.0452 (6)0.0555 (7)0.0346 (6)0.0043 (5)0.0035 (5)0.0101 (5)
N140.0440 (8)0.0629 (10)0.0438 (8)0.0083 (7)0.0001 (6)0.0189 (7)
C110.0358 (8)0.0343 (8)0.0329 (8)0.0030 (6)0.0012 (6)0.0047 (6)
C120.0400 (8)0.0310 (8)0.0355 (8)0.0016 (6)0.0001 (6)0.0017 (6)
C130.0456 (9)0.0356 (8)0.0321 (8)0.0004 (7)0.0025 (6)0.0017 (6)
C140.0375 (8)0.0390 (9)0.0388 (8)0.0033 (7)0.0039 (6)0.0080 (7)
C150.0355 (8)0.0594 (11)0.0491 (10)0.0088 (8)0.0057 (7)0.0159 (8)
C160.0388 (9)0.0579 (11)0.0399 (8)0.0045 (8)0.0070 (7)0.0128 (8)
C170.0386 (8)0.0377 (8)0.0329 (8)0.0024 (7)0.0012 (6)0.0031 (6)
O30.0653 (11)0.0345 (9)0.0534 (10)0.0000.0071 (8)0.000
Geometric parameters (Å, º) top
N1—C21.484 (2)C7—H7A0.99
N1—C7i1.489 (2)C7—H7B0.99
N1—H1A0.92O1—C171.2504 (19)
N1—H1B0.92O2—C171.2751 (19)
C2—C31.509 (2)N14—C141.3773 (19)
C2—H2A0.99N14—H14A0.88
C2—H2B0.99N14—H14B0.88
C3—N41.461 (2)C11—C161.390 (2)
C3—H3A0.99C11—C121.391 (2)
C3—H3B0.99C11—C171.496 (2)
N4—C51.470 (2)C12—C131.383 (2)
N4—H40.92C12—H120.95
C5—C61.513 (3)C13—C141.401 (2)
C5—H5A0.99C13—H130.95
C5—H5B0.99C14—C151.392 (2)
C6—C71.519 (3)C15—C161.379 (2)
C6—H6A0.99C15—H150.95
C6—H6B0.99C16—H160.95
C7—N1i1.489 (2)O3—H30.95
C2—N1—C7i114.98 (13)H6A—C6—H6B107.6
C2—N1—H1A108.5N1i—C7—C6110.85 (14)
C7i—N1—H1A108.5N1i—C7—H7A109.5
C2—N1—H1B108.5C6—C7—H7A109.5
C7i—N1—H1B108.5N1i—C7—H7B109.5
H1A—N1—H1B107.5C6—C7—H7B109.5
N1—C2—C3110.46 (14)H7A—C7—H7B108.1
N1—C2—H2A109.6C14—N14—H14A120.0
C3—C2—H2A109.6C14—N14—H14B120.0
N1—C2—H2B109.6H14A—N14—H14B120.0
C3—C2—H2B109.6C16—C11—C12117.88 (14)
H2A—C2—H2B108.1C16—C11—C17121.09 (14)
N4—C3—C2110.61 (13)C12—C11—C17121.03 (14)
N4—C3—H3A109.5C13—C12—C11120.93 (14)
C2—C3—H3A109.5C13—C12—H12119.5
N4—C3—H3B109.5C11—C12—H12119.5
C2—C3—H3B109.5C12—C13—C14120.80 (15)
H3A—C3—H3B108.1C12—C13—H13119.6
C3—N4—C5112.09 (13)C14—C13—H13119.6
C3—N4—H4109.2N14—C14—C15121.77 (15)
C5—N4—H4109.2N14—C14—C13120.07 (15)
N4—C5—C6111.78 (14)C15—C14—C13118.16 (14)
N4—C5—H5A109.3C16—C15—C14120.38 (15)
C6—C5—H5A109.3C16—C15—H15119.8
N4—C5—H5B109.3C14—C15—H15119.8
C6—C5—H5B109.3C15—C16—C11121.80 (15)
H5A—C5—H5B107.9C15—C16—H16119.1
C5—C6—C7114.21 (15)C11—C16—H16119.1
C5—C6—H6A108.7O1—C17—O2122.67 (14)
C7—C6—H6A108.7O1—C17—C11119.85 (13)
C5—C6—H6B108.7O2—C17—C11117.49 (14)
C7—C6—H6B108.7
C7i—N1—C2—C3168.79 (13)C12—C13—C14—C152.5 (2)
N1—C2—C3—N459.59 (17)N14—C14—C15—C16178.78 (16)
C2—C3—N4—C5178.29 (14)C13—C14—C15—C160.8 (3)
C3—N4—C5—C6179.67 (15)C14—C15—C16—C111.0 (3)
N4—C5—C6—C763.0 (2)C12—C11—C16—C151.2 (3)
C5—C6—C7—N1i69.14 (18)C17—C11—C16—C15178.25 (16)
C16—C11—C12—C130.5 (2)C16—C11—C17—O1170.55 (15)
C17—C11—C12—C13179.94 (14)C12—C11—C17—O18.9 (2)
C11—C12—C13—C142.3 (2)C16—C11—C17—O29.4 (2)
C12—C13—C14—N14177.12 (15)C12—C11—C17—O2171.20 (15)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O10.951.792.7374 (16)171
N1—H1A···O20.921.772.6875 (17)175
N1—H1B···N4i0.922.132.8467 (19)134
N4—H4···O1i0.922.293.1113 (16)148
N14—H14A···O2ii0.882.163.0215 (19)167
N14—H14B···O2iii0.882.132.9163 (19)148
C2—H2B···O3i0.992.543.409 (2)146
C7—H7B···O30.992.393.295 (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, z1/2.
(III) Cyclam/3-hydroxybenzoic acid/water (1/2/2) top
Crystal data top
C10H26N4·2(C7H5O3)·2(H2O)F(000) = 552
Mr = 512.60Dx = 1.276 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 3059 reflections
a = 9.1490 (2) Åθ = 2.9–27.7°
b = 12.8557 (4) ŵ = 0.10 mm1
c = 12.4022 (4) ÅT = 150 K
β = 113.8540 (19)°Block, colourless
V = 1334.10 (7) Å30.30 × 0.28 × 0.22 mm
Z = 2
Data collection top
Kappa-CCD
diffractometer
2693 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.039
Graphite monochromatorθmax = 27.7°, θmin = 2.9°
ϕ scans, and ω scans with κ offsetsh = 011
9540 measured reflectionsk = 160
3059 independent reflectionsl = 1614
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0769P)2 + 0.064P]
where P = (Fo2 + 2Fc2)/3
3059 reflections(Δ/σ)max = 0.006
337 parametersΔρmax = 0.28 e Å3
2 restraintsΔρmin = 0.22 e Å3
Crystal data top
C10H26N4·2(C7H5O3)·2(H2O)V = 1334.10 (7) Å3
Mr = 512.60Z = 2
Monoclinic, PcMo Kα radiation
a = 9.1490 (2) ŵ = 0.10 mm1
b = 12.8557 (4) ÅT = 150 K
c = 12.4022 (4) Å0.30 × 0.28 × 0.22 mm
β = 113.8540 (19)°
Data collection top
Kappa-CCD
diffractometer
2693 reflections with I > 2σ(I)
9540 measured reflectionsRint = 0.039
3059 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0372 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 0.96Δρmax = 0.28 e Å3
3059 reflectionsΔρmin = 0.22 e Å3
337 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.5723 (2)0.32367 (15)0.57229 (17)0.0239 (4)
N40.7056 (2)0.12662 (15)0.69316 (18)0.0251 (4)
N80.6276 (2)0.16803 (15)0.88924 (18)0.0243 (4)
N110.4963 (2)0.36556 (15)0.76843 (18)0.0251 (4)
C20.5972 (3)0.2305 (2)0.5107 (2)0.0291 (5)
C30.7380 (3)0.1685 (2)0.5947 (2)0.0296 (5)
C50.8480 (3)0.0760 (2)0.7802 (2)0.0311 (5)
C60.8194 (3)0.0330 (2)0.8843 (2)0.0315 (5)
C70.7843 (3)0.1162 (2)0.9581 (2)0.0299 (5)
C90.5960 (3)0.26053 (19)0.9486 (2)0.0268 (5)
C100.4563 (3)0.32158 (19)0.8624 (2)0.0287 (5)
C120.3597 (3)0.4242 (2)0.6829 (2)0.0314 (5)
C130.3947 (3)0.46555 (19)0.5803 (2)0.0330 (6)
C140.4203 (3)0.3804 (2)0.5046 (2)0.0301 (5)
O210.8359 (2)0.43950 (14)0.60223 (15)0.0312 (4)
O220.69780 (19)0.45404 (14)0.40887 (15)0.0284 (4)
O231.0635 (2)0.66554 (15)0.27524 (17)0.0349 (4)
C210.9370 (3)0.55276 (17)0.4965 (2)0.0223 (4)
C220.9444 (2)0.57165 (18)0.3878 (2)0.0241 (5)
C231.0500 (3)0.64649 (19)0.3795 (2)0.0257 (5)
C241.1453 (3)0.70285 (19)0.4788 (2)0.0288 (5)
C251.1381 (3)0.6836 (2)0.5867 (2)0.0302 (5)
C261.0345 (3)0.60751 (19)0.5959 (2)0.0260 (5)
C270.8164 (3)0.47597 (17)0.5029 (2)0.0234 (5)
O310.4749 (2)0.04641 (15)0.54280 (16)0.0351 (4)
O320.3921 (2)0.02004 (14)0.35045 (15)0.0328 (4)
O330.0767 (2)0.21645 (16)0.23956 (16)0.0363 (4)
C310.2539 (3)0.06855 (18)0.4502 (2)0.0230 (4)
C320.1468 (3)0.11166 (18)0.3459 (2)0.0243 (5)
C330.0303 (3)0.18236 (18)0.3467 (2)0.0264 (5)
C340.0267 (3)0.2115 (2)0.4536 (2)0.0283 (5)
C350.1333 (3)0.1674 (2)0.5581 (2)0.0304 (5)
C360.2469 (3)0.09532 (19)0.5575 (2)0.0266 (5)
C370.3820 (3)0.00625 (19)0.4484 (2)0.0247 (5)
O10.6614 (2)0.30803 (15)0.23733 (18)0.0382 (4)
O20.4509 (3)0.14876 (15)0.22633 (17)0.0403 (5)
H1A0.65660.36860.58750.029*
H1B0.57290.30330.64360.029*
H40.62340.07920.66480.030*
H8A0.62500.18810.81730.029*
H8B0.54690.12050.87550.029*
H11A0.58290.40910.80100.030*
H2A0.61780.25240.44160.035*
H2B0.49980.18670.48230.035*
H3A0.76090.11040.55150.036*
H3B0.83370.21370.62610.036*
H5A0.93670.12700.80930.037*
H5B0.88080.01850.74170.037*
H6A0.91500.00670.93560.038*
H6B0.72830.01600.85440.038*
H7A0.78170.08391.02980.036*
H7B0.87070.16880.98320.036*
H9A0.69220.30530.97940.032*
H9B0.57190.23781.01590.032*
H10A0.36230.27530.82750.034*
H10B0.42850.37840.90460.034*
H12A0.33440.48320.72370.038*
H12B0.26480.37820.65180.038*
H13A0.30450.50990.53000.040*
H13B0.49150.50970.61210.040*
H14A0.32950.33100.47970.036*
H14B0.42460.41150.43290.036*
H230.99950.62730.22220.052*
H22A0.87790.53370.31980.024 (7)*
H241.21560.75470.47280.038 (8)*
H251.20360.72220.65440.034 (8)*
H261.03100.59340.67000.041 (8)*
H330.15090.24890.24820.076 (14)*
H320.15210.09330.27330.035 (8)*
H340.04880.26150.45510.044 (9)*
H350.12880.18660.63070.034 (8)*
H360.31870.06470.62900.029 (7)*
H110.59140.26490.23540.056*
H120.66950.35450.28700.056*
H210.44310.11880.16410.056*
H220.42180.10810.26680.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0265 (9)0.0255 (9)0.0214 (10)0.0013 (7)0.0115 (8)0.0011 (7)
N40.0266 (9)0.0239 (10)0.0272 (10)0.0011 (7)0.0133 (8)0.0003 (8)
N80.0290 (9)0.0236 (9)0.0216 (10)0.0023 (7)0.0117 (8)0.0015 (7)
N110.0273 (9)0.0249 (10)0.0255 (10)0.0004 (8)0.0133 (8)0.0005 (8)
C20.0417 (13)0.0266 (12)0.0245 (12)0.0044 (10)0.0190 (10)0.0025 (9)
C30.0360 (12)0.0290 (12)0.0319 (13)0.0017 (9)0.0220 (11)0.0021 (10)
C50.0307 (11)0.0301 (12)0.0344 (14)0.0064 (9)0.0151 (10)0.0022 (10)
C60.0342 (12)0.0286 (12)0.0327 (14)0.0059 (9)0.0144 (10)0.0066 (10)
C70.0269 (11)0.0338 (13)0.0261 (12)0.0031 (9)0.0076 (10)0.0030 (10)
C90.0343 (12)0.0256 (12)0.0232 (12)0.0027 (9)0.0146 (10)0.0038 (9)
C100.0374 (12)0.0253 (12)0.0319 (13)0.0004 (9)0.0229 (11)0.0019 (9)
C120.0306 (12)0.0320 (13)0.0355 (14)0.0085 (10)0.0173 (11)0.0045 (10)
C130.0340 (12)0.0260 (12)0.0375 (15)0.0074 (10)0.0130 (11)0.0075 (10)
C140.0272 (11)0.0349 (13)0.0260 (12)0.0003 (9)0.0084 (10)0.0061 (10)
O210.0332 (8)0.0376 (10)0.0236 (9)0.0069 (7)0.0123 (7)0.0033 (7)
O220.0284 (8)0.0299 (9)0.0253 (9)0.0054 (6)0.0092 (7)0.0015 (7)
O230.0326 (9)0.0451 (11)0.0289 (9)0.0069 (7)0.0146 (7)0.0029 (8)
C210.0247 (10)0.0223 (11)0.0219 (11)0.0036 (8)0.0115 (8)0.0004 (8)
C220.0221 (10)0.0268 (11)0.0228 (11)0.0001 (8)0.0085 (9)0.0007 (9)
C230.0219 (9)0.0292 (11)0.0277 (12)0.0021 (9)0.0117 (9)0.0040 (9)
C240.0244 (10)0.0264 (11)0.0375 (13)0.0003 (9)0.0146 (10)0.0002 (10)
C250.0268 (11)0.0286 (12)0.0333 (13)0.0015 (9)0.0103 (10)0.0085 (10)
C260.0267 (11)0.0293 (12)0.0237 (11)0.0037 (9)0.0118 (9)0.0018 (9)
C270.0262 (10)0.0226 (11)0.0231 (11)0.0008 (8)0.0116 (9)0.0003 (9)
O310.0405 (10)0.0423 (11)0.0250 (9)0.0110 (8)0.0157 (8)0.0049 (8)
O320.0409 (9)0.0384 (10)0.0227 (9)0.0121 (8)0.0165 (7)0.0023 (7)
O330.0369 (9)0.0446 (11)0.0307 (10)0.0119 (8)0.0172 (8)0.0082 (8)
C310.0230 (10)0.0240 (11)0.0251 (11)0.0023 (8)0.0130 (9)0.0023 (9)
C320.0249 (10)0.0255 (11)0.0253 (11)0.0003 (8)0.0131 (9)0.0006 (9)
C330.0272 (11)0.0264 (11)0.0287 (12)0.0018 (9)0.0146 (10)0.0032 (9)
C340.0272 (11)0.0270 (12)0.0340 (13)0.0005 (9)0.0159 (10)0.0043 (9)
C350.0307 (12)0.0358 (13)0.0292 (13)0.0037 (10)0.0168 (10)0.0102 (10)
C360.0264 (11)0.0324 (12)0.0227 (11)0.0008 (9)0.0116 (9)0.0025 (9)
C370.0278 (10)0.0250 (11)0.0250 (12)0.0000 (9)0.0143 (9)0.0013 (9)
O10.0383 (10)0.0427 (11)0.0363 (10)0.0041 (8)0.0177 (8)0.0051 (8)
O20.0577 (12)0.0356 (10)0.0354 (10)0.0047 (8)0.0271 (9)0.0056 (8)
Geometric parameters (Å, º) top
N1—C21.487 (3)C13—H13B0.99
N1—C141.492 (3)C14—H14A0.99
N1—H1A0.92C14—H14B0.99
N1—H1B0.92O21—C271.262 (3)
N4—C51.466 (3)O22—C271.262 (3)
N4—C31.470 (3)O23—C231.371 (3)
N4—H40.92O23—H230.84
N8—C91.487 (3)C21—C261.387 (3)
N8—C71.496 (3)C21—C221.398 (3)
N8—H8A0.92C21—C271.506 (3)
N8—H8B0.92C22—C231.396 (3)
N11—C101.469 (3)C22—H22A0.95
N11—C121.477 (3)C23—C241.390 (3)
N11—H11A0.92C24—C251.389 (4)
C2—C31.515 (4)C24—H240.95
C2—H2A0.99C25—C261.398 (4)
C2—H2B0.99C25—H250.95
C3—H3A0.99C26—H260.95
C3—H3B0.99O31—C371.247 (3)
C5—C61.521 (4)O32—C371.267 (3)
C5—H5A0.99O33—C331.365 (3)
C5—H5B0.99O33—H330.84
C6—C71.523 (4)C31—C321.384 (3)
C6—H6A0.99C31—C361.400 (3)
C6—H6B0.99C31—C371.523 (3)
C7—H7A0.99C32—C331.404 (3)
C7—H7B0.99C32—H320.95
C9—C101.512 (3)C33—C341.391 (4)
C9—H9A0.99C34—C351.390 (4)
C9—H9B0.99C34—H340.95
C10—H10A0.99C35—C361.395 (3)
C10—H10B0.99C35—H350.95
C12—C131.528 (4)C36—H360.95
C12—H12A0.99O1—H110.84
C12—H12B0.99O1—H120.84
C13—C141.520 (4)O2—H210.84
C13—H13A0.99O2—H220.84
C2—N1—C14113.99 (19)C13—C12—H12A109.2
C2—N1—H1A108.8N11—C12—H12B109.2
C14—N1—H1A108.8C13—C12—H12B109.2
C2—N1—H1B108.8H12A—C12—H12B107.9
C14—N1—H1B108.8C14—C13—C12113.6 (2)
H1A—N1—H1B107.6C14—C13—H13A108.9
C5—N4—C3110.88 (19)C12—C13—H13A108.9
C5—N4—H4109.5C14—C13—H13B108.9
C3—N4—H4109.5C12—C13—H13B108.9
C9—N8—C7114.02 (19)H13A—C13—H13B107.7
C9—N8—H8A108.7N1—C14—C13110.2 (2)
C7—N8—H8A108.7N1—C14—H14A109.6
C9—N8—H8B108.7C13—C14—H14A109.6
C7—N8—H8B108.7N1—C14—H14B109.6
H8A—N8—H8B107.6C13—C14—H14B109.6
C10—N11—C12110.87 (18)H14A—C14—H14B108.1
C10—N11—H11A109.5C23—O23—H23109.5
C12—N11—H11A109.5C26—C21—C22120.3 (2)
N1—C2—C3109.57 (19)C26—C21—C27120.5 (2)
N1—C2—H2A109.8C22—C21—C27119.1 (2)
C3—C2—H2A109.8C23—C22—C21119.7 (2)
N1—C2—H2B109.8C23—C22—H22A120.2
C3—C2—H2B109.8C21—C22—H22A120.2
H2A—C2—H2B108.2O23—C23—C24118.6 (2)
N4—C3—C2111.3 (2)O23—C23—C22121.4 (2)
N4—C3—H3A109.4C24—C23—C22120.0 (2)
C2—C3—H3A109.4C25—C24—C23120.2 (2)
N4—C3—H3B109.4C25—C24—H24119.9
C2—C3—H3B109.4C23—C24—H24119.9
H3A—C3—H3B108.0C24—C25—C26120.1 (2)
N4—C5—C6112.3 (2)C24—C25—H25120.0
N4—C5—H5A109.1C26—C25—H25120.0
C6—C5—H5A109.1C21—C26—C25119.7 (2)
N4—C5—H5B109.1C21—C26—H26120.1
C6—C5—H5B109.1C25—C26—H26120.1
H5A—C5—H5B107.9O21—C27—O22123.3 (2)
C5—C6—C7113.9 (2)O21—C27—C21118.5 (2)
C5—C6—H6A108.8O22—C27—C21118.2 (2)
C7—C6—H6A108.8C33—O33—H33109.5
C5—C6—H6B108.8C32—C31—C36120.2 (2)
C7—C6—H6B108.8C32—C31—C37119.8 (2)
H6A—C6—H6B107.7C36—C31—C37120.0 (2)
N8—C7—C6110.9 (2)C31—C32—C33120.3 (2)
N8—C7—H7A109.5C31—C32—H32119.8
C6—C7—H7A109.5C33—C32—H32119.8
N8—C7—H7B109.5O33—C33—C34123.9 (2)
C6—C7—H7B109.5O33—C33—C32116.6 (2)
H7A—C7—H7B108.1C34—C33—C32119.5 (2)
N8—C9—C10110.07 (19)C35—C34—C33120.1 (2)
N8—C9—H9A109.6C35—C34—H34119.9
C10—C9—H9A109.6C33—C34—H34119.9
N8—C9—H9B109.6C34—C35—C36120.6 (2)
C10—C9—H9B109.6C34—C35—H35119.7
H9A—C9—H9B108.2C36—C35—H35119.7
N11—C10—C9110.5 (2)C35—C36—C31119.3 (2)
N11—C10—H10A109.5C35—C36—H36120.3
C9—C10—H10A109.5C31—C36—H36120.3
N11—C10—H10B109.5O31—C37—O32123.8 (2)
C9—C10—H10B109.5O31—C37—C31118.9 (2)
H10A—C10—H10B108.1O32—C37—C31117.2 (2)
N11—C12—C13111.95 (19)H11—O1—H12109.3
N11—C12—H12A109.2H21—O2—H22109.6
C14—N1—C2—C3170.0 (2)C22—C21—C26—C251.5 (3)
C5—N4—C3—C2174.1 (2)C27—C21—C26—C25175.6 (2)
N1—C2—C3—N464.5 (3)C24—C25—C26—C211.2 (3)
C3—N4—C5—C6179.2 (2)C26—C21—C27—O2120.7 (3)
N4—C5—C6—C764.6 (3)C22—C21—C27—O21162.2 (2)
C9—N8—C7—C6171.4 (2)C26—C21—C27—O22157.0 (2)
C5—C6—C7—N866.8 (3)C22—C21—C27—O2220.2 (3)
C7—N8—C9—C10166.9 (2)C36—C31—C32—C330.1 (3)
C12—N11—C10—C9179.23 (19)C37—C31—C32—C33178.7 (2)
N8—C9—C10—N1165.4 (3)C31—C32—C33—O33176.2 (2)
C10—N11—C12—C13176.7 (2)C31—C32—C33—C342.1 (3)
N11—C12—C13—C1464.2 (3)O33—C33—C34—C35175.5 (2)
C2—N1—C14—C13172.7 (2)C32—C33—C34—C352.7 (4)
C12—C13—C14—N168.5 (3)C33—C34—C35—C361.3 (4)
C26—C21—C22—C230.4 (3)C34—C35—C36—C310.8 (4)
C27—C21—C22—C23176.75 (19)C32—C31—C36—C351.4 (3)
C21—C22—C23—O23178.4 (2)C37—C31—C36—C35177.2 (2)
C21—C22—C23—C241.0 (3)C32—C31—C37—O31178.2 (2)
O23—C23—C24—C25178.2 (2)C36—C31—C37—O313.2 (3)
C22—C23—C24—C251.2 (3)C32—C31—C37—O325.1 (3)
C23—C24—C25—C260.1 (3)C36—C31—C37—O32173.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O20.841.942.776 (3)171
O1—H12···O220.841.922.754 (3)176
O2—H21···O31i0.841.892.714 (3)167
O2—H22···O320.842.022.835 (3)163
O23—H23···O21ii0.841.842.674 (3)171
O33—H33···O1iii0.841.832.660 (3)168
N1—H1A···O210.921.822.729 (3)169
N1—H1B···N110.922.102.839 (3)137
N4—H4···O310.922.253.114 (3)155
N8—H8A···N40.922.112.848 (3)136
N8—H8B···O32iv0.921.852.767 (3)177
N11—H11A···O22v0.922.203.035 (3)150
Symmetry codes: (i) x, y, z1/2; (ii) x, y+1, z1/2; (iii) x1, y, z; (iv) x, y, z+1/2; (v) x, y+1, z+1/2.
(IV) Cyclam/5-hydroxyisophthalic acid/methanol (1/1/1) top
Crystal data top
C10H26N4·C8H4O5·CH4OF(000) = 896
Mr = 414.50Dx = 1.293 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4886 reflections
a = 9.7666 (3) Åθ = 2.7–27.6°
b = 13.9931 (6) ŵ = 0.10 mm1
c = 15.9476 (6) ÅT = 150 K
β = 102.280 (2)°Block, colourless
V = 2129.61 (14) Å30.20 × 0.16 × 0.16 mm
Z = 4
Data collection top
Kappa-CCD
diffractometer
3059 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.075
Graphite monochromatorθmax = 27.6°, θmin = 2.7°
ϕ scans, and ω scans with κ offsetsh = 012
16817 measured reflectionsk = 018
4886 independent reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.193 w = 1/[σ2(Fo2) + (0.1053P)2 + 0.1884P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4886 reflectionsΔρmax = 0.47 e Å3
266 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (4)
Crystal data top
C10H26N4·C8H4O5·CH4OV = 2129.61 (14) Å3
Mr = 414.50Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.7666 (3) ŵ = 0.10 mm1
b = 13.9931 (6) ÅT = 150 K
c = 15.9476 (6) Å0.20 × 0.16 × 0.16 mm
β = 102.280 (2)°
Data collection top
Kappa-CCD
diffractometer
3059 reflections with I > 2σ(I)
16817 measured reflectionsRint = 0.075
4886 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.193H-atom parameters constrained
S = 1.05Δρmax = 0.47 e Å3
4886 reflectionsΔρmin = 0.32 e Å3
266 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.28613 (19)0.59374 (14)0.40901 (11)0.0292 (5)
C120.3425 (2)0.61409 (18)0.33063 (14)0.0320 (5)
C130.4722 (2)0.55579 (19)0.32817 (15)0.0337 (5)
N140.57326 (19)0.56396 (14)0.40894 (12)0.0308 (5)
C150.6978 (2)0.50564 (18)0.41352 (15)0.0346 (6)
C160.8014 (2)0.5236 (2)0.49773 (17)0.0389 (6)
C170.7420 (3)0.50876 (17)0.57711 (15)0.0341 (6)
N210.0456 (3)0.48284 (16)0.12437 (14)0.0488 (6)
C220.0886 (4)0.4343 (2)0.15241 (19)0.0611 (9)
C230.2054 (3)0.4885 (2)0.12855 (19)0.0617 (10)
N240.2063 (2)0.48064 (18)0.03620 (16)0.0501 (6)
C250.3113 (3)0.5417 (3)0.0107 (3)0.0748 (12)
C260.3052 (4)0.5350 (3)0.0829 (3)0.0768 (12)
C270.1725 (5)0.5744 (2)0.1364 (3)0.0781 (13)
O10.55216 (17)0.78419 (13)0.03018 (10)0.0377 (4)
O20.36115 (17)0.71160 (13)0.00513 (9)0.0376 (4)
O30.01127 (17)0.60616 (13)0.25663 (10)0.0392 (5)
O40.02053 (16)0.68147 (13)0.38008 (10)0.0356 (4)
O50.47451 (17)0.81443 (12)0.34667 (9)0.0327 (4)
C10.3712 (2)0.74406 (15)0.14980 (13)0.0242 (5)
C20.2388 (2)0.70583 (16)0.18104 (13)0.0258 (5)
C30.1841 (2)0.70156 (15)0.26955 (13)0.0246 (5)
C40.2631 (2)0.73728 (15)0.32608 (13)0.0240 (5)
C50.3951 (2)0.77726 (16)0.29466 (13)0.0249 (5)
C60.4491 (2)0.77928 (16)0.20676 (13)0.0254 (5)
C70.4340 (2)0.74732 (17)0.05428 (13)0.0271 (5)
C80.0408 (2)0.66008 (16)0.30436 (14)0.0285 (5)
O60.0207 (2)0.78983 (16)0.52975 (13)0.0588 (6)
C90.0994 (3)0.7340 (2)0.59708 (19)0.0567 (8)
H11A0.34920.61600.45620.035*
H11B0.20410.62740.40530.035*
H12A0.36550.68290.32930.038*
H12B0.26930.59970.27890.038*
H13A0.44590.48790.31720.040*
H13B0.51480.57870.28080.040*
H140.59990.62690.41730.037*
H15A0.74210.52140.36490.041*
H15B0.67130.43720.40920.041*
H16A0.88260.48050.50090.047*
H16B0.83610.59010.49780.047*
H17A0.80920.53370.62780.041*
H17B0.65380.54540.57120.041*
H21A0.05670.49790.06720.059*
H21B0.04320.53930.15430.059*
H22A0.08320.37000.12600.073*
H22B0.10780.42600.21550.073*
H23A0.19730.55670.14330.074*
H23B0.29550.46430.16250.074*
H240.22340.41810.02370.060*
H25A0.40570.52250.04250.090*
H25B0.29550.60880.02590.090*
H26A0.31430.46710.09830.092*
H26B0.38580.57020.09640.092*
H27A0.17820.57310.19760.094*
H27B0.16140.64180.12010.094*
H50.43240.80820.39810.049*
H20.18520.68250.14220.031*
H40.22680.73430.38620.029*
H60.53990.80490.18530.030*
H6A0.00920.75910.48350.088*
H9A0.19480.72570.58800.085*
H9B0.05490.67130.59790.085*
H9C0.10280.76640.65200.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0236 (10)0.0340 (11)0.0266 (9)0.0024 (8)0.0023 (8)0.0016 (8)
C120.0295 (12)0.0373 (13)0.0262 (11)0.0012 (10)0.0007 (9)0.0020 (10)
C130.0323 (13)0.0396 (13)0.0284 (12)0.0007 (11)0.0045 (10)0.0004 (10)
N140.0268 (10)0.0330 (11)0.0308 (10)0.0016 (8)0.0022 (8)0.0027 (8)
C150.0296 (13)0.0382 (13)0.0379 (13)0.0030 (10)0.0118 (10)0.0069 (10)
C160.0229 (12)0.0436 (15)0.0484 (15)0.0026 (11)0.0036 (11)0.0105 (12)
C170.0293 (12)0.0329 (13)0.0360 (13)0.0005 (10)0.0019 (10)0.0019 (10)
N210.0758 (18)0.0364 (12)0.0352 (12)0.0071 (12)0.0141 (11)0.0004 (9)
C220.088 (3)0.0510 (18)0.0392 (16)0.0278 (18)0.0017 (16)0.0005 (13)
C230.059 (2)0.061 (2)0.0498 (17)0.0290 (17)0.0231 (15)0.0259 (15)
N240.0374 (13)0.0489 (15)0.0592 (15)0.0028 (11)0.0008 (11)0.0212 (12)
C250.0427 (18)0.065 (2)0.120 (3)0.0152 (17)0.024 (2)0.043 (2)
C260.069 (2)0.055 (2)0.121 (3)0.0179 (19)0.054 (3)0.014 (2)
C270.131 (4)0.0406 (18)0.081 (3)0.011 (2)0.064 (3)0.0016 (16)
O10.0337 (10)0.0547 (11)0.0217 (8)0.0090 (8)0.0006 (7)0.0053 (7)
O20.0342 (9)0.0607 (12)0.0177 (7)0.0052 (8)0.0054 (7)0.0003 (7)
O30.0336 (9)0.0500 (11)0.0313 (9)0.0126 (8)0.0011 (7)0.0070 (8)
O40.0300 (9)0.0471 (10)0.0254 (8)0.0085 (8)0.0036 (7)0.0013 (7)
O50.0328 (9)0.0465 (10)0.0186 (7)0.0083 (8)0.0053 (6)0.0001 (7)
C10.0264 (12)0.0262 (11)0.0188 (10)0.0037 (9)0.0023 (8)0.0026 (8)
C20.0277 (11)0.0296 (12)0.0204 (10)0.0001 (9)0.0055 (9)0.0005 (8)
C30.0250 (11)0.0259 (11)0.0217 (10)0.0015 (9)0.0020 (9)0.0018 (8)
C40.0246 (11)0.0290 (11)0.0169 (9)0.0022 (9)0.0008 (8)0.0008 (8)
C50.0253 (11)0.0290 (12)0.0206 (10)0.0000 (9)0.0053 (9)0.0005 (8)
C60.0230 (11)0.0305 (12)0.0214 (10)0.0017 (9)0.0017 (9)0.0035 (8)
C70.0266 (12)0.0340 (13)0.0200 (10)0.0013 (10)0.0031 (9)0.0035 (9)
C80.0276 (12)0.0328 (12)0.0243 (11)0.0012 (10)0.0039 (9)0.0026 (9)
O60.0631 (14)0.0643 (14)0.0450 (11)0.0118 (12)0.0029 (10)0.0050 (10)
C90.062 (2)0.0567 (19)0.0473 (17)0.0056 (16)0.0036 (15)0.0043 (14)
Geometric parameters (Å, º) top
N11—C17i1.486 (3)N24—H240.92
N11—C121.496 (3)C25—C261.484 (5)
N11—H11A0.92C25—H25A0.99
N11—H11B0.92C25—H25B0.99
C12—C131.514 (3)C26—C271.497 (6)
C12—H12A0.99C26—H26A0.99
C12—H12B0.99C26—H26B0.99
C13—N141.451 (3)C27—N21ii1.522 (4)
C13—H13A0.99C27—H27A0.99
C13—H13B0.99C27—H27B0.99
N14—C151.454 (3)O1—C71.248 (3)
N14—H140.92O2—C71.268 (3)
C15—C161.521 (4)O3—C81.254 (3)
C15—H15A0.99O4—C81.265 (3)
C15—H15B0.99O5—C51.354 (2)
C16—C171.514 (3)O5—H50.84
C16—H16A0.99C1—C21.390 (3)
C16—H16B0.99C1—C61.393 (3)
C17—N11i1.486 (3)C1—C71.517 (3)
C17—H17A0.99C2—C31.400 (3)
C17—H17B0.99C2—H20.95
N21—C221.460 (4)C3—C41.398 (3)
N21—C27ii1.522 (4)C3—C81.508 (3)
N21—H21A0.92C4—C51.397 (3)
N21—H21B0.92C4—H40.95
C22—C231.485 (5)C5—C61.389 (3)
C22—H22A0.99C6—H60.95
C22—H22B0.99O6—C91.415 (4)
C23—N241.479 (4)O6—H6A0.84
C23—H23A0.99C9—H9A0.98
C23—H23B0.99C9—H9B0.98
N24—C251.457 (4)C9—H9C0.98
C17i—N11—C12114.89 (18)C22—C23—H23B109.1
C17i—N11—H11A108.5H23A—C23—H23B107.8
C12—N11—H11A108.5C25—N24—C23112.8 (3)
C17i—N11—H11B108.5C25—N24—H24109.0
C12—N11—H11B108.5C23—N24—H24109.0
H11A—N11—H11B107.5N24—C25—C26111.3 (3)
N11—C12—C13112.18 (18)N24—C25—H25A109.4
N11—C12—H12A109.2C26—C25—H25A109.4
C13—C12—H12A109.2N24—C25—H25B109.4
N11—C12—H12B109.2C26—C25—H25B109.4
C13—C12—H12B109.2H25A—C25—H25B108.0
H12A—C12—H12B107.9C25—C26—C27113.2 (3)
N14—C13—C12110.44 (19)C25—C26—H26A108.9
N14—C13—H13A109.6C27—C26—H26A108.9
C12—C13—H13A109.6C25—C26—H26B108.9
N14—C13—H13B109.6C27—C26—H26B108.9
C12—C13—H13B109.6H26A—C26—H26B107.7
H13A—C13—H13B108.1C26—C27—N21ii111.3 (3)
C13—N14—C15113.84 (19)C26—C27—H27A109.4
C13—N14—H14108.8N21ii—C27—H27A109.4
C15—N14—H14108.8C26—C27—H27B109.4
N14—C15—C16110.1 (2)N21ii—C27—H27B109.4
N14—C15—H15A109.6H27A—C27—H27B108.0
C16—C15—H15A109.6C5—O5—H5109.5
N14—C15—H15B109.6C2—C1—C6119.86 (19)
C16—C15—H15B109.6C2—C1—C7121.20 (19)
H15A—C15—H15B108.2C6—C1—C7118.9 (2)
C17—C16—C15114.5 (2)C1—C2—C3120.27 (19)
C17—C16—H16A108.6C1—C2—H2119.9
C15—C16—H16A108.6C3—C2—H2119.9
C17—C16—H16B108.6C4—C3—C2119.4 (2)
C15—C16—H16B108.6C4—C3—C8119.77 (18)
H16A—C16—H16B107.6C2—C3—C8120.85 (18)
N11i—C17—C16111.9 (2)C5—C4—C3120.38 (18)
N11i—C17—H17A109.2C5—C4—H4119.8
C16—C17—H17A109.2C3—C4—H4119.8
N11i—C17—H17B109.2O5—C5—C6117.82 (19)
C16—C17—H17B109.2O5—C5—C4122.63 (18)
H17A—C17—H17B107.9C6—C5—C4119.55 (18)
C22—N21—C27ii114.7 (3)C5—C6—C1120.6 (2)
C22—N21—H21A108.6C5—C6—H6119.7
C27ii—N21—H21A108.6C1—C6—H6119.7
C22—N21—H21B108.6O1—C7—O2125.2 (2)
C27ii—N21—H21B108.6O1—C7—C1118.14 (19)
H21A—N21—H21B107.6O2—C7—C1116.7 (2)
N21—C22—C23111.8 (3)O3—C8—O4123.4 (2)
N21—C22—H22A109.2O3—C8—C3118.22 (19)
C23—C22—H22A109.2O4—C8—C3118.34 (19)
N21—C22—H22B109.2C9—O6—H6A109.5
C23—C22—H22B109.2O6—C9—H9A109.5
H22A—C22—H22B107.9O6—C9—H9B109.5
N24—C23—C22112.6 (2)H9A—C9—H9B109.5
N24—C23—H23A109.1O6—C9—H9C109.5
C22—C23—H23A109.1H9A—C9—H9C109.5
N24—C23—H23B109.1H9B—C9—H9C109.5
C17i—N11—C12—C1354.1 (3)C2—C3—C4—C50.3 (3)
N11—C12—C13—N1450.1 (3)C8—C3—C4—C5179.00 (19)
C12—C13—N14—C15176.73 (19)C3—C4—C5—O5178.7 (2)
C13—N14—C15—C16176.37 (19)C3—C4—C5—C61.5 (3)
N14—C15—C16—C1755.1 (3)O5—C5—C6—C1178.58 (19)
C15—C16—C17—N11i69.8 (3)C4—C5—C6—C11.7 (3)
C27ii—N21—C22—C23172.5 (3)C2—C1—C6—C50.5 (3)
N21—C22—C23—N2475.2 (3)C7—C1—C6—C5179.8 (2)
C22—C23—N24—C25173.9 (3)C2—C1—C7—O1178.7 (2)
C23—N24—C25—C26177.6 (3)C6—C1—C7—O12.0 (3)
N24—C25—C26—C2766.3 (4)C2—C1—C7—O21.6 (3)
C25—C26—C27—N21ii63.9 (4)C6—C1—C7—O2177.7 (2)
C6—C1—C2—C30.7 (3)C4—C3—C8—O3160.9 (2)
C7—C1—C2—C3178.6 (2)C2—C3—C8—O319.8 (3)
C1—C2—C3—C40.9 (3)C4—C3—C8—O419.1 (3)
C1—C2—C3—C8179.9 (2)C2—C3—C8—O4160.2 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O2iii0.841.722.560 (2)174
O6—H6A···O40.842.002.827 (3)169
N11—H11A···O1iv0.921.952.801 (3)154
N11—H11B···O40.921.912.818 (2)169
N14—H14···O2iv0.922.643.494 (3)154
N21—H21A···N24ii0.921.982.752 (3)140
N21—H21B···O30.921.862.690 (3)149
N24—H24···O2ii0.922.363.222 (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.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC10H26N4·2(C11H15O2)·4(H2O)C10H26N4·2(C7H6NO2)·H2OC10H26N4·2(C7H5O3)·2(H2O)C10H26N4·C8H4O5·CH4O
Mr632.87492.62512.60414.50
Crystal system, space groupMonoclinic, P21/nMonoclinic, C2/cMonoclinic, PcMonoclinic, P21/c
Temperature (K)150150150150
a, b, c (Å)8.8604 (2), 6.8025 (1), 27.8239 (6)19.6462 (8), 9.0374 (4), 15.2051 (7)9.1490 (2), 12.8557 (4), 12.4022 (4)9.7666 (3), 13.9931 (6), 15.9476 (6)
β (°) 91.044 (1) 94.127 (2) 113.8540 (19) 102.280 (2)
V3)1676.75 (6)2692.7 (2)1334.10 (7)2129.61 (14)
Z2424
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.090.100.10
Crystal size (mm)0.35 × 0.25 × 0.220.32 × 0.29 × 0.140.30 × 0.28 × 0.220.20 × 0.16 × 0.16
Data collection
DiffractometerKappa-CCD
diffractometer
Kappa-CCD
diffractometer
Kappa-CCD
diffractometer
Kappa-CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10461, 3796, 2910 12532, 3016, 2156 9540, 3059, 2693 16817, 4886, 3059
Rint0.0350.0460.0390.075
(sin θ/λ)max1)0.6490.6460.6530.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.124, 1.05 0.047, 0.117, 1.07 0.037, 0.105, 0.96 0.061, 0.193, 1.05
No. of reflections3796301630594886
No. of parameters199160337266
No. of restraints0020
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.220.20, 0.190.28, 0.220.47, 0.32

Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997b), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O3—H31···O1i0.951.752.689 (2)171
O3—H32···O10.951.832.767 (2)168
O4—H41···O30.872.253.075 (2)159
O4—H42···O2ii0.871.832.688 (2)171
N11—H11A···O3iii0.921.922.792 (2)158
N11—H11B···N14iv0.922.132.818 (2)131
N14—H14···O20.922.553.270 (2)136
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z; (iii) x+1, y, z+1; (iv) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O10.951.792.7374 (16)171
N1—H1A···O20.921.772.6875 (17)175
N1—H1B···N4i0.922.132.8467 (19)134
N4—H4···O1i0.922.293.1113 (16)148
N14—H14A···O2ii0.882.163.0215 (19)167
N14—H14B···O2iii0.882.132.9163 (19)148
C2—H2B···O3i0.992.543.409 (2)146
C7—H7B···O30.992.393.295 (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, z1/2.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O20.841.942.776 (3)171
O1—H12···O220.841.922.754 (3)176
O2—H21···O31i0.841.892.714 (3)167
O2—H22···O320.842.022.835 (3)163
O23—H23···O21ii0.841.842.674 (3)171
O33—H33···O1iii0.841.832.660 (3)168
N1—H1A···O210.921.822.729 (3)169
N1—H1B···N110.922.102.839 (3)137
N4—H4···O310.922.253.114 (3)155
N8—H8A···N40.922.112.848 (3)136
N8—H8B···O32iv0.921.852.767 (3)177
N11—H11A···O22v0.922.203.035 (3)150
Symmetry codes: (i) x, y, z1/2; (ii) x, y+1, z1/2; (iii) x1, y, z; (iv) x, y, z+1/2; (v) x, y+1, z+1/2.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O2i0.841.722.560 (2)174
O6—H6A···O40.842.002.827 (3)169
N11—H11A···O1ii0.921.952.801 (3)154
N11—H11B···O40.921.912.818 (2)169
N21—H21A···N24iii0.921.982.752 (3)140
N21—H21B···O30.921.862.690 (3)149
N24—H24···O2iii0.922.363.222 (3)156
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+3/2, z+1/2; (iii) x, y+1, z.
 

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