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In the title compound, C20H40N8·H2O, the organic mol­ecule crystallizes with one water mol­ecule located within the mol­ecular cavity of the octaaza macrocycle. The two mol­ecules are linked via two weak O-H...N hydrogen bonds. The assembly has noncrystallographic C2 axial symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110010413/sk3369sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110010413/sk3369Isup2.hkl
Contains datablock I

CCDC reference: 774918

Comment top

Polyaza macrocyclic compounds with tetrahedrally arranged nitrogen lone-pair orbitals (LPOs) have been exploited for complexation with ions (Mazloum et al., 2002). Some of these compounds have attracted intense attention due to their molecular diamond lattice conformation. In fact, both theoretical (Galasso et al., 2001) and experimental studies (Dale et al., 1991, 1992) of the molecular structures and spectroscopic properties of this class of compounds have been reported. The results of these studies revealed that 1,3,7,9,13,15,19,21-octaazapentacyclo[19.3.1.13,7.19,13.115,19]octaeicosane exists in two conformations, one in which the eight N atoms are diequatorially substituted (D2d symmetry) and one with an equatorial–axial substitution in each 1,3-diazane ring (S4 symmetry). Density functional theory (DFT) calculations (Galasso et al., 2001) showed that the S4 conformer is more stable than the D2d conformer by 2.6 kcal mol-1 (1 kcal mol-1 = 4.184 kJ mol-1), due to dipole–dipole repulsion between the axial lone pairs of the N atoms. A previous X-ray structural investigation of a 1:1 complex of 1,3,7,9,13,15,19,21-octaazapentacyclo[19.3.1.13,7.19,13.115,19]octaeicosane and benzene showed that the 16-membered pentacyclooctaaza ring exists in a less symmetric but more stable conformation (Murray-Rust, 1975). However, the most favourable conformation is avoided [achieved?] when 1,3,7,9,13,15,19,21-octaazapentacyclo[19.3.1.13,7.19,13.115,19]octaeicosane crystallizes as a 1:2 dichloromethane complex (Dale et al., 1991), where the D2d conformation exhibits a syn-axial orientation of the N-atom lone pairs, showing the so-called rabbit-ear effect (Hutchins et al., 1968). Repulsion is avoided due to the presence of intermolecular interactions between the N atoms and the H atoms of the dichloromethane molecules (Dale et al., 1991). [Please check rephrasing]

In recent years, we have used these classes of polycyclic polyaza compounds, as preformed Mannich reagents, in the synthesis of several heterocyclic systems (Rivera et al., 2005; Rivera & Maldonado 2006). During these studies, crystals of the title monohydrate, (I), were obtained when the reaction was carried out according to the usual technique, i.e. mixed aqueous formaldehyde and 1,3-propanodiamine (Krassig, 1956). A broad band with a maximum at about 3400 cm-1 is observed in the IR spectrum, which is attributed to water molecules. Although selective inclusion of non-protic solvents such as benzene, dioxane and dichloromethane by 1,3,7,9,13,15,19,21-octaazapentacyclo[19.3.1.13,7.19,13.115,19]octaeicosane is known (Dale et al., 1991), where host–guest association determines the conformational preference of the organic molecule, as far as we are aware this is the first example of a complex with a protic solvent. The current X-ray study confirms that this solid is a 1:1 complex of the 1,3,7,9,13,15,19,21-octaazapentacyclo[19.3.1.13,7.19,13.115,19]octaeicosane macrocycle and a water molecule. Only two of the eight N atoms of the macrocycle are involved in hydrogen bonding with the one molecule of water. Our results indicate that the title macrocycle affords efficient binding affinity for both apolar and polar solvents due to the chelation effect, and could thus form complexes with metallic cations (Mazloum et al., 2002). [Please check rephrasing]

The molecular structure and atom-numbering scheme for (I) are shown in Fig. 1. All atoms of both the organic molecule and the water molecule are located on general positions. Selected angles and bond lengths are listed in Table 1. Careful examination of the crystal structure of the adduct shows that the 1,3-diazane rings adopt two different conformations, which are only controlled by the binding of the water molecule. One of the conformations is hydrogen-bonded and the other is not (Fig. 1). Our X-ray results show that the hydrogen-bond interactions in (I) do not generate a large change in the tetrahedral character of the N-atom lone pairs. The marked tetrahedral character of the N atoms in (I) is nicely illustrated by the sums of the C—N—C bond angles, which range from 330.2 to 336.4°. The individual C—N—C bond angles in (I) are around 109.2 (1)–113.8 (1)° (Table 1), close to normal tetrahedral bond angles. Nevertheless, as can be seen in Table 1, the smallest values are for the N atoms involved in hydrogen bonding (N1 and N5). This X-ray analysis also shows that the aminal C—N bond lengths for N atoms neighbouring N atoms involved in hydrogen-bond interactions are shorter than the other bonds.

The presence of hydrogen bonds to atoms N1 and N5 might enhance the structural consequences, and thus the formation of this class of intermolecular interactions strongly influences the conformation of the molecule, forming the less stable configuration with a 1,3-diaxial disposition of the nitrogen lone pairs and forcing the hexahydropyrimidine ring to adopt a diequatorial disubstitution. This can be explained on the basis of a preference for the conformation where the lone pair is located in the proximity of the electrostatic dipole–dipole interaction, the so-called reverse anomeric effect (Grein & Deslongchamps, 1992). On the other hand, for the other two rings, the stable conformation is conserved. The ring structure is approximately C2 symmetric with a twofold axis passing through atom O1. On the basis of our results, we propose the existence of a third conformation for the organic molecule of (I).

Fig 2. shows the crystal packing in (I), with the channels extending along a and accommodating the water molecules. Each channel is composed of two symmetry-equivalent positions of the organic molecule. No remarkable intermolecular contacts exist in the structure.

The text was unclear in several places, with some very long sentences. Rephrasing has been attempted. Please check that your original meaning has not been altered.

Experimental top

To a stirred solution of formaldehyde (16.4 ml, 0.22 mmol) 40% in ethanol, 1,3-propanediamine (8 ml, 0.11 mmol) and a solution of NaOH (0.25 M; 0.1 ml, 0.02 mmol) were slowly added dropwise. After stirring for 12 h at room temperature, the solvent was removed at reduced pressure. Recrystallization of the resulting solid from ethanol–water (80:20 v/v) gave the title compound, (I) (m.p. 438–439 K).

Refinement top

All H atoms were discernible in difference Fourier maps and could be refined to a reasonable geometry. According to common practice, H atoms attached to C atoms were nevertheless kept in ideal positions during the refinement, with C—H = 0.96 Å [Please check added text] and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The packing of (I), viewed along the a axis. Dashed lines indicate hydrogen bonds.
1,3,7,9,13,15,19,21- octaazapentacyclo[19.3.1.13,7.19,13.115,19]octaeicosane monohydrate top
Crystal data top
C20H40N8·H2OF(000) = 904
Mr = 410.6Dx = 1.189 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 34331 reflections
a = 12.4858 (2) Åθ = 3.6–66.7°
b = 18.8016 (3) ŵ = 0.61 mm1
c = 9.8354 (2) ÅT = 120 K
β = 96.6010 (13)°Prism, colourless
V = 2293.58 (7) Å30.43 × 0.37 × 0.26 mm
Z = 4
Data collection top
Oxford Xcalibur
diffractometer with Atlas detector (Gemini Ultra Cu)
4010 independent reflections
Radiation source: X-ray tube3741 reflections with I > 3σ(I)
Mirror monochromatorRint = 0.026
Detector resolution: 10.3784 pixels mm-1θmax = 66.9°, θmin = 3.6°
Rotation method data acquisition using ω scansh = 1414
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 2222
Tmin = 0.716, Tmax = 1.000l = 1111
43976 measured reflections
Refinement top
Refinement on F2162 constraints
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 2.73(Δ/σ)max = 0.010
4010 reflectionsΔρmax = 0.18 e Å3
268 parametersΔρmin = 0.16 e Å3
0 restraints
Crystal data top
C20H40N8·H2OV = 2293.58 (7) Å3
Mr = 410.6Z = 4
Monoclinic, P21/cCu Kα radiation
a = 12.4858 (2) ŵ = 0.61 mm1
b = 18.8016 (3) ÅT = 120 K
c = 9.8354 (2) Å0.43 × 0.37 × 0.26 mm
β = 96.6010 (13)°
Data collection top
Oxford Xcalibur
diffractometer with Atlas detector (Gemini Ultra Cu)
4010 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
3741 reflections with I > 3σ(I)
Tmin = 0.716, Tmax = 1.000Rint = 0.026
43976 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 2.73Δρmax = 0.18 e Å3
4010 reflectionsΔρmin = 0.16 e Å3
268 parameters
Special details top

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.24870 (7)0.50680 (5)0.53334 (9)0.0310 (3)
N10.38229 (7)0.36634 (5)0.57067 (9)0.0244 (3)
N20.19774 (7)0.33245 (5)0.54868 (9)0.0210 (3)
N30.00772 (7)0.33013 (5)0.49029 (9)0.0211 (3)
N40.01287 (7)0.40613 (5)0.28881 (9)0.0209 (3)
N50.10119 (7)0.50676 (4)0.25727 (9)0.0208 (3)
N60.27885 (7)0.49056 (4)0.19759 (9)0.0199 (3)
N70.46364 (7)0.46138 (5)0.20327 (9)0.0218 (3)
N80.48311 (7)0.36824 (5)0.37563 (10)0.0247 (3)
C10.30160 (8)0.31745 (6)0.50380 (11)0.0225 (3)
C20.39264 (9)0.35652 (6)0.72029 (11)0.0300 (4)
C30.28398 (10)0.36518 (6)0.77346 (11)0.0303 (4)
C40.19979 (9)0.31777 (6)0.69483 (11)0.0258 (3)
C50.10956 (8)0.29702 (6)0.46613 (10)0.0218 (3)
C60.00125 (8)0.40284 (5)0.43936 (10)0.0210 (3)
C70.08721 (9)0.28909 (6)0.43488 (11)0.0264 (3)
C80.10995 (9)0.29365 (6)0.27892 (11)0.0279 (3)
C90.11287 (9)0.37103 (6)0.23339 (11)0.0253 (3)
C100.00881 (8)0.47902 (6)0.24068 (11)0.0223 (3)
C110.16928 (8)0.46474 (5)0.17538 (10)0.0203 (3)
C120.09970 (9)0.58156 (6)0.21370 (11)0.0236 (3)
C130.21395 (9)0.61071 (6)0.22461 (12)0.0266 (3)
C140.28520 (9)0.56361 (6)0.14849 (11)0.0239 (3)
C150.35503 (8)0.44341 (5)0.14252 (11)0.0218 (3)
C160.48046 (8)0.44545 (6)0.34824 (11)0.0229 (3)
C170.54895 (9)0.42883 (6)0.13334 (12)0.0270 (3)
C180.56274 (9)0.34940 (6)0.16378 (13)0.0301 (4)
C190.57485 (9)0.33653 (6)0.31779 (13)0.0293 (4)
C200.48725 (9)0.35432 (7)0.52133 (12)0.0286 (4)
H1A0.2972940.3233030.4063620.027*
H1B0.3220210.2693740.5272610.027*
H2A0.4422810.3909480.7632780.036*
H2B0.4205560.3098970.7428930.036*
H3A0.2614420.413930.7641380.0363*
H3B0.2904320.3530520.8688630.0363*
H4A0.2183240.2687960.7122450.031*
H4B0.130260.3277810.7230550.031*
H5A0.1193080.3012830.3710660.0261*
H5B0.1084960.247660.4908820.0261*
H6A0.0612760.4293870.4755960.0252*
H6B0.0619970.4255690.4725950.0252*
H7A0.1491470.3053470.4754420.0317*
H7B0.0778090.2402060.461840.0317*
H8A0.0544570.2689470.2380210.0335*
H8B0.1780610.2716320.2495540.0335*
H9A0.1201090.3732240.1352460.0304*
H9B0.1729940.3945320.2665680.0304*
H10A0.0536560.508440.2904030.0267*
H10B0.0374040.4811780.1459010.0267*
H11A0.1674530.4156920.2021140.0244*
H11B0.1427840.4690650.0801810.0244*
H12A0.0579240.6090120.2708220.0283*
H12B0.0671660.5850540.1206370.0283*
H13A0.21280.6578580.186980.0319*
H13B0.2429090.6134310.3192010.0319*
H14A0.2610910.5652510.0522710.0286*
H14B0.3583930.5799660.1646190.0286*
H15A0.3500550.4492560.0450270.0262*
H15B0.3391710.3950830.1645090.0262*
H16A0.4242320.4669840.3929990.0275*
H16B0.5468140.4666050.3877340.0275*
H17A0.6159050.4529330.1596670.0324*
H17B0.5333340.4357980.0363950.0324*
H18A0.5008940.3240610.1216340.0361*
H18B0.6256380.3321870.1265710.0361*
H19A0.576610.2863030.3354270.0351*
H19B0.6404660.3580370.3588310.0351*
H20A0.5094920.3060620.5397430.0343*
H20B0.540280.3845920.5703770.0343*
H1O0.2806 (12)0.4647 (9)0.5348 (14)0.0372*
H1P0.2158 (13)0.5056 (7)0.4481 (17)0.0372*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0305 (5)0.0311 (5)0.0305 (5)0.0028 (3)0.0002 (4)0.0038 (3)
N10.0201 (5)0.0314 (5)0.0210 (5)0.0026 (4)0.0004 (4)0.0032 (4)
N20.0194 (5)0.0260 (5)0.0176 (5)0.0004 (3)0.0015 (3)0.0005 (3)
N30.0175 (5)0.0252 (5)0.0206 (5)0.0022 (3)0.0025 (3)0.0006 (3)
N40.0183 (5)0.0240 (5)0.0199 (5)0.0019 (3)0.0008 (3)0.0019 (3)
N50.0191 (5)0.0206 (4)0.0230 (5)0.0008 (3)0.0041 (3)0.0013 (3)
N60.0185 (5)0.0193 (4)0.0221 (5)0.0004 (3)0.0031 (3)0.0001 (3)
N70.0172 (4)0.0248 (5)0.0242 (5)0.0004 (3)0.0057 (3)0.0011 (4)
N80.0190 (5)0.0268 (5)0.0284 (5)0.0027 (4)0.0040 (4)0.0031 (4)
C10.0207 (6)0.0243 (5)0.0223 (5)0.0003 (4)0.0014 (4)0.0013 (4)
C20.0265 (6)0.0398 (7)0.0222 (6)0.0047 (5)0.0040 (5)0.0047 (5)
C30.0319 (6)0.0396 (7)0.0186 (6)0.0025 (5)0.0005 (5)0.0015 (5)
C40.0252 (6)0.0326 (6)0.0196 (5)0.0003 (4)0.0022 (4)0.0038 (4)
C50.0213 (6)0.0224 (5)0.0216 (5)0.0019 (4)0.0025 (4)0.0012 (4)
C60.0191 (5)0.0245 (5)0.0195 (5)0.0012 (4)0.0022 (4)0.0022 (4)
C70.0219 (6)0.0301 (6)0.0270 (6)0.0068 (4)0.0017 (4)0.0043 (5)
C80.0253 (6)0.0302 (6)0.0271 (6)0.0095 (5)0.0024 (4)0.0001 (5)
C90.0213 (6)0.0320 (6)0.0219 (5)0.0042 (4)0.0011 (4)0.0015 (4)
C100.0169 (5)0.0255 (5)0.0241 (5)0.0012 (4)0.0014 (4)0.0025 (4)
C110.0193 (5)0.0218 (5)0.0200 (5)0.0005 (4)0.0025 (4)0.0004 (4)
C120.0237 (6)0.0218 (5)0.0256 (6)0.0037 (4)0.0041 (4)0.0026 (4)
C130.0276 (6)0.0191 (5)0.0332 (6)0.0000 (4)0.0046 (5)0.0022 (4)
C140.0224 (6)0.0227 (5)0.0268 (6)0.0026 (4)0.0043 (4)0.0033 (4)
C150.0211 (5)0.0227 (5)0.0219 (5)0.0004 (4)0.0037 (4)0.0019 (4)
C160.0185 (5)0.0255 (5)0.0247 (6)0.0007 (4)0.0021 (4)0.0021 (4)
C170.0206 (6)0.0324 (6)0.0295 (6)0.0003 (4)0.0095 (4)0.0000 (5)
C180.0236 (6)0.0303 (6)0.0378 (7)0.0037 (5)0.0104 (5)0.0057 (5)
C190.0206 (6)0.0281 (6)0.0400 (7)0.0035 (4)0.0073 (5)0.0024 (5)
C200.0193 (6)0.0372 (6)0.0286 (6)0.0007 (4)0.0000 (5)0.0075 (5)
Geometric parameters (Å, º) top
O1—H1O0.886 (16)C5—H5B0.96
O1—H1P0.890 (16)C6—H6A0.96
N1—C11.4630 (13)C6—H6B0.96
N1—C21.4739 (14)C7—C81.5299 (16)
N1—C201.4663 (15)C7—H7A0.96
N2—C11.4448 (14)C7—H7B0.96
N2—C41.4611 (14)C8—C91.5214 (16)
N2—C51.4524 (13)C8—H8A0.96
N3—C51.4596 (13)C8—H8B0.96
N3—C61.4558 (13)C9—H9A0.96
N3—C71.4659 (14)C9—H9B0.96
N4—C61.4724 (13)C10—H10A0.96
N4—C91.4613 (13)C10—H10B0.96
N4—C101.4526 (14)C11—H11A0.96
N5—C101.4606 (13)C11—H11B0.96
N5—C111.4673 (14)C12—C131.5205 (15)
N5—C121.4697 (13)C12—H12A0.96
N6—C111.4443 (13)C12—H12B0.96
N6—C141.4611 (13)C13—C141.5131 (16)
N6—C151.4499 (14)C13—H13A0.96
N7—C151.4574 (13)C13—H13B0.96
N7—C161.4484 (14)C14—H14A0.96
N7—C171.4665 (15)C14—H14B0.96
N8—C161.4761 (14)C15—H15A0.96
N8—C191.4631 (15)C15—H15B0.96
N8—C201.4518 (15)C16—H16A0.96
C1—H1A0.96C16—H16B0.96
C1—H1B0.96C17—C181.5288 (16)
C2—C31.5178 (17)C17—H17A0.96
C2—H2A0.96C17—H17B0.96
C2—H2B0.96C18—C191.5242 (17)
C3—C41.5201 (16)C18—H18A0.96
C3—H3A0.96C18—H18B0.96
C3—H3B0.96C19—H19A0.96
C4—H4A0.96C19—H19B0.96
C4—H4B0.96C20—H20A0.96
C5—H5A0.96C20—H20B0.96
H1O—O1—H1P98.7 (13)N4—C9—C8109.36 (8)
C1—N1—C2110.30 (9)N4—C9—H9A109.4708
C1—N1—C20110.48 (9)N4—C9—H9B109.4704
C2—N1—C20109.39 (8)C8—C9—H9A109.472
C1—N2—C4110.42 (8)C8—C9—H9B109.4718
C1—N2—C5112.89 (8)H9A—C9—H9B109.5783
C4—N2—C5112.94 (8)N4—C10—N5111.59 (8)
C5—N3—C6112.24 (8)N4—C10—H10A109.4716
C5—N3—C7113.41 (8)N4—C10—H10B109.4713
C6—N3—C7109.85 (8)N5—C10—H10A109.4714
C6—N4—C9109.71 (8)N5—C10—H10B109.471
C6—N4—C10111.36 (8)H10A—C10—H10B107.2606
C9—N4—C10111.40 (8)N5—C11—N6109.55 (8)
C10—N5—C11110.07 (8)N5—C11—H11A109.4713
C10—N5—C12109.20 (8)N5—C11—H11B109.4719
C11—N5—C12110.11 (8)N6—C11—H11A109.4715
C11—N6—C14110.63 (8)N6—C11—H11B109.4704
C11—N6—C15112.88 (8)H11A—C11—H11B109.3906
C14—N6—C15112.85 (8)N5—C12—C13110.13 (8)
C15—N7—C16112.24 (8)N5—C12—H12A109.4715
C15—N7—C17113.75 (8)N5—C12—H12B109.4716
C16—N7—C17110.15 (8)C13—C12—H12A109.4708
C16—N8—C19109.39 (9)C13—C12—H12B109.4712
C16—N8—C20110.79 (9)H12A—C12—H12B108.8039
C19—N8—C20111.70 (8)C12—C13—C14110.75 (9)
N1—C1—N2109.62 (8)C12—C13—H13A109.4714
N1—C1—H1A109.4714C12—C13—H13B109.4718
N1—C1—H1B109.4709C14—C13—H13A109.4714
N2—C1—H1A109.4714C14—C13—H13B109.4709
N2—C1—H1B109.4711H13A—C13—H13B108.1644
H1A—C1—H1B109.3177N6—C14—C13109.23 (9)
N1—C2—C3110.57 (9)N6—C14—H14A109.471
N1—C2—H2A109.4719N6—C14—H14B109.4715
N1—C2—H2B109.4705C13—C14—H14A109.4709
C3—C2—H2A109.472C13—C14—H14B109.4714
C3—C2—H2B109.4708H14A—C14—H14B109.7107
H2A—C2—H2B108.3514N6—C15—N7108.94 (8)
C2—C3—C4110.79 (9)N6—C15—H15A109.4707
C2—C3—H3A109.471N6—C15—H15B109.471
C2—C3—H3B109.4719N7—C15—H15A109.4708
C4—C3—H3A109.4704N7—C15—H15B109.4715
C4—C3—H3B109.4711H15A—C15—H15B109.9985
H3A—C3—H3B108.1163N7—C16—N8112.38 (8)
N2—C4—C3108.82 (9)N7—C16—H16A109.4716
N2—C4—H4A109.4711N7—C16—H16B109.4706
N2—C4—H4B109.4721N8—C16—H16A109.4713
C3—C4—H4A109.4704N8—C16—H16B109.4712
C3—C4—H4B109.4712H16A—C16—H16B106.396
H4A—C4—H4B110.115N7—C17—C18112.79 (9)
N2—C5—N3109.39 (8)N7—C17—H17A109.4715
N2—C5—H5A109.4711N7—C17—H17B109.4708
N2—C5—H5B109.4708C18—C17—H17A109.4712
N3—C5—H5A109.4715C18—C17—H17B109.4708
N3—C5—H5B109.4709H17A—C17—H17B105.9366
H5A—C5—H5B109.55C17—C18—C19110.23 (10)
N3—C6—N4112.35 (8)C17—C18—H18A109.4713
N3—C6—H6A109.4709C17—C18—H18B109.4708
N3—C6—H6B109.4715C19—C18—H18A109.4714
N4—C6—H6A109.4715C19—C18—H18B109.4712
N4—C6—H6B109.4711H18A—C18—H18B108.7024
H6A—C6—H6B106.4317N8—C19—C18109.21 (9)
N3—C7—C8113.09 (9)N8—C19—H19A109.4718
N3—C7—H7A109.4716N8—C19—H19B109.4708
N3—C7—H7B109.4711C18—C19—H19A109.4707
C8—C7—H7A109.4714C18—C19—H19B109.4717
C8—C7—H7B109.4714H19A—C19—H19B109.7305
H7A—C7—H7B105.5945N1—C20—N8111.54 (8)
C7—C8—C9110.13 (9)N1—C20—H20A109.4714
C7—C8—H8A109.4709N1—C20—H20B109.4712
C7—C8—H8B109.4709N8—C20—H20A109.4718
C9—C8—H8A109.4718N8—C20—H20B109.4703
C9—C8—H8B109.4708H20A—C20—H20B107.3198
H8A—C8—H8B108.8068
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.886 (16)2.248 (16)3.1226 (12)169.3 (12)
O1—H1P···N50.890 (16)2.226 (15)3.1008 (12)167.4 (15)

Experimental details

Crystal data
Chemical formulaC20H40N8·H2O
Mr410.6
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)12.4858 (2), 18.8016 (3), 9.8354 (2)
β (°) 96.6010 (13)
V3)2293.58 (7)
Z4
Radiation typeCu Kα
µ (mm1)0.61
Crystal size (mm)0.43 × 0.37 × 0.26
Data collection
DiffractometerOxford Xcalibur
diffractometer with Atlas detector (Gemini Ultra Cu)
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.716, 1.000
No. of measured, independent and
observed [I > 3σ(I)] reflections
43976, 4010, 3741
Rint0.026
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.125, 2.73
No. of reflections4010
No. of parameters268
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SUPERFLIP (Palatinus & Chapuis, 2007), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).

Selected geometric parameters (Å, º) top
N1—C11.4630 (13)N5—C101.4606 (13)
N1—C21.4739 (14)N5—C111.4673 (14)
N1—C201.4663 (15)N5—C121.4697 (13)
N2—C11.4448 (14)N6—C111.4443 (13)
N2—C41.4611 (14)N6—C141.4611 (13)
N2—C51.4524 (13)N6—C151.4499 (14)
N3—C51.4596 (13)N7—C151.4574 (13)
N3—C61.4558 (13)N7—C161.4484 (14)
N3—C71.4659 (14)N7—C171.4665 (15)
N4—C61.4724 (13)N8—C161.4761 (14)
N4—C91.4613 (13)N8—C191.4631 (15)
N4—C101.4526 (14)
C1—N1—C2110.30 (9)C10—N5—C11110.07 (8)
C1—N1—C20110.48 (9)C10—N5—C12109.20 (8)
C2—N1—C20109.39 (8)C11—N5—C12110.11 (8)
C1—N2—C4110.42 (8)C11—N6—C14110.63 (8)
C1—N2—C5112.89 (8)C11—N6—C15112.88 (8)
C4—N2—C5112.94 (8)C14—N6—C15112.85 (8)
C5—N3—C6112.24 (8)C15—N7—C16112.24 (8)
C5—N3—C7113.41 (8)C15—N7—C17113.75 (8)
C6—N3—C7109.85 (8)C16—N7—C17110.15 (8)
C6—N4—C9109.71 (8)C16—N8—C19109.39 (9)
C6—N4—C10111.36 (8)C16—N8—C20110.79 (9)
C9—N4—C10111.40 (8)C19—N8—C20111.70 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.886 (16)2.248 (16)3.1226 (12)169.3 (12)
O1—H1P···N50.890 (16)2.226 (15)3.1008 (12)167.4 (15)
 

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