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Acta Cryst. (2008). E64, o1078-o1079    [ doi:10.1107/S1600536808013652 ]

(-)-N,N'-Bis[(1S,2R,5S)-6,6-dimethyl-bicyclo[3.1.1]heptan-2-ylmethyl]pyridine-2,6-dicarboxamide monohydrate

S. Bernès, F. J. Pérez-Flores and R. Gutiérrez

Abstract top

The title compound, C27H39N3O2·H2O, is a chiral pyridine-2,6-dicarboxamide derivative including cis-myrtanyl groups as amine substituents. The pyridine-2,6-dicarboxamide core approximates C2 point symmetry and a solvent water molecule lies on the pseudo-twofold axis. The water molecule serves both as acceptor and donor for efficient hydrogen bonds involving N-H and C=O functional groups as donor and acceptor groups, respectively. As a result, each water molecule in the crystal structure is tetrahedrally bonded to three symmetry-related molecules, forming a three-dimensional supramolecular network. Such an arrangement is a common feature found in the majority of X-ray-characterized symmetrically substituted pyridine-2,6-dicarboxamide derivatives.

Comment top

Nowadays, reactions conducted in the absence of solvents under mild reaction conditions are becoming an important method in laboratories worldwide as an environment–friendly technique for the efficient syntheses of organic molecules. The main advantages of solvent-free organic synthesis are shorter reaction times, minimum waste and generally higher yields, operational simplicity as well as reduction of thermal degradative byproducts along with cleaner work–up (Tanaka & Toda, 2000). As part of an ongoing program aiming to develop simpler and eco–friendly methods for organic transformations under solvent–free conditions (Tovar et al., 2007; Vázquez et al., 2004), we engaged the preparation of chiral pincer ligands (Pérez-Flores & Gutiérrez, 2008). The title compound resulted from this research, by introducing chiral cis–myrtanyl groups as amine substituents.

The X–ray characterized monohydrate has the expected molecular geometry (Fig. 1). The pyridine–2,6–dicarboxamide core approximates a C2 point symmetry, with the pseudo 2–fold axis passing through N1 and C24. The guest water molecule O3 is placed on the pseudo 2–fold axis and is involved in two N—H···O hydrogen bonds within the asymmetric unit (Fig. 1 and Table 1, lines 1 and 2). The same water molecule is a donor group for two C═O···H intermolecular hydrogen bonds of relatively strong strength (Table 1, lines 3 and 4). As a consequence, a three–dimensional supramolecular structure is formed in the crystal structure, with water molecules being bonded in a tetrahedral arrangement (Fig. 2) to three symmetry–related molecules. Such a feature seems to be common for symmetrically substituted pyridine–2,6–dicarboxamide derivatives. These compounds are generally crystallized as hydrates, and, at least for X–ray characterized compounds, water molecules form hydrogen bonds similar to those observed in the title molecule (e.g. Yu et al., 1999; Qi et al., 2002; Jain et al., 2004; Odriozola et al., 2004).

Related literature top

For background to the solvent–free synthesis used for the preparation of the title compound, see: Tanaka & Toda (2000); Vázquez et al. (2004); Tovar et al. (2007); Pérez-Flores & Gutiérrez (2008). For hydrates of pyridine-2,6-dicarboxamide derivatives, see: Yu et al. (1999); Qi et al. (2002); Jain et al. (2004); Odriozola et al. (2004).

Experimental top

Under solvent–free conditions, (-)-cis–myrtanylamine (0.38 g, 2.5 mmol) and 2,6–pyridinedicarbonyl dichloride (0.30 g, 1.5 mmol) were mixed at room temperature, giving a white solid. The crude was recrystallized from EtOH affording the corresponding dicarboxamide (98% yield).

Refinement top

C–bonded H atoms were placed in idealized positions and refined with a riding model approximation. Constrained C—H distances: 0.93 (aromatic CH), 0.96 (methyl CH3), 0.97 (methylene CH2) or 0.98 Å (methine CH). Isotropic displacement parameters: Uiso= 1.5Ueq(carrier C atom) for methyl groups and Uiso = 1.2Ueq(carrier C atom) otherwise. Methyl groups were considered as rigid rotating groups. Other H atoms (amine groups and water molecule) were found in a difference map and refined freely. Measured Friedel pairs (287) were merged.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and POV-RAY (Cason, 2004); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit for the title compound, with the numbering scheme. Displacement ellipsoids for non–H atoms are drawn at the 40% probability level. H atoms are presented as small spheres of arbitrary radius. Dashed bonds are hydrogen bonds involving N—H groups as donor groups.
[Figure 2] Fig. 2. A part of the packing structure for the title compound, showing the four H bonds formed by a water molecule, in a tetrahedral geometry (dashed bonds). Symmetry codes: (i) 1+x, y, z; (ii) 2-x, 1/2+y, 2-z. H atoms not involved in hydrogen bonds have been omitted for clarity.
(-)-N,N'-Bis[(1S,2R,5S)-6,6-dimethyl- bicyclo[3.1.1]heptan-2-ylmethyl]pyridine-2,6-dicarboxamide monohydrate top
Crystal data top
C27H39N3O2·H2ODx = 1.140 Mg m−3
Mr = 455.63Melting point = 398–401 K
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 60 reflections
a = 6.8476 (11) Åθ = 4.6–12.5º
b = 12.1101 (14) ŵ = 0.07 mm−1
c = 16.012 (2) ÅT = 298 (1) K
β = 91.173 (15)ºCell measurement pressure: 101(2) kPa
V = 1327.5 (3) Å3Plate, colourless
Z = 20.6 × 0.6 × 0.2 mm
F000 = 496
Data collection top
Bruker P4
diffractometer		Rint = 0.035
Radiation source: fine-focus sealed tubeθmax = 27.5º
Monochromator: Graphiteθmin = 2.1º
T = 298(1) Kh = −8→6
P = 101(2) kPak = −1→15
ω scansl = −20→20
Absorption correction: none3 standard reflections
6391 measured reflections every 97 reflections
3180 independent reflections intensity decay: 2%
2580 reflections with I > 2σ(I)
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)] = 0.040H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.107  w = 1/[σ2(Fo2) + (0.0551P)2 + 0.0694P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3180 reflectionsΔρmax = 0.14 e Å−3
319 parametersΔρmin = −0.13 e Å−3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.037 (7)
Crystal data top
C27H39N3O2·H2OV = 1327.5 (3) Å3
Mr = 455.63Z = 2
Monoclinic, P21Mo Kα
a = 6.8476 (11) ŵ = 0.07 mm−1
b = 12.1101 (14) ÅT = 298 (1) K
c = 16.012 (2) Å0.6 × 0.6 × 0.2 mm
β = 91.173 (15)º
Data collection top
Bruker P4
diffractometer		Rint = 0.035
Absorption correction: none3 standard reflections
6391 measured reflections every 97 reflections
3180 independent reflections intensity decay: 2%
2580 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.107Δρmax = 0.14 e Å−3
S = 1.04Δρmin = −0.13 e Å−3
3180 reflectionsAbsolute structure: ?
319 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.6298 (3)0.24506 (16)0.95082 (10)0.0520 (4)
N20.5268 (3)0.37490 (17)0.81930 (11)0.0558 (5)
H20.636 (4)0.374 (2)0.8414 (14)0.049 (6)*
N30.9690 (3)0.29137 (18)1.03447 (12)0.0576 (5)
H30.926 (3)0.330 (2)0.9926 (17)0.058 (7)*
O10.2258 (2)0.29762 (18)0.81492 (11)0.0731 (5)
O20.9360 (4)0.13912 (17)1.11410 (13)0.0893 (6)
C10.4749 (3)0.30035 (19)0.63787 (13)0.0529 (5)
H1A0.46420.24240.68030.063*
C20.5749 (3)0.4058 (2)0.66831 (13)0.0556 (5)
H2A0.71220.38690.67930.067*
C30.5733 (5)0.4954 (2)0.59935 (16)0.0724 (7)
H3A0.70400.52570.59550.087*
H3B0.48770.55490.61620.087*
C40.5059 (6)0.4548 (3)0.51078 (18)0.0866 (9)
H4A0.40460.50370.48930.104*
H4B0.61540.45890.47340.104*
C50.4292 (4)0.3386 (2)0.51132 (15)0.0737 (7)
H5A0.38430.31080.45670.088*
C60.2858 (3)0.3192 (2)0.58333 (14)0.0598 (5)
C70.5754 (4)0.2641 (2)0.55738 (16)0.0737 (7)
H7A0.71030.28780.55360.088*
H7B0.56130.18620.54450.088*
C80.1734 (5)0.2103 (3)0.5733 (2)0.0834 (8)
H8A0.08570.21520.52590.125*
H8B0.10030.19640.62270.125*
H8C0.26410.15100.56500.125*
C90.1402 (4)0.4092 (3)0.6038 (2)0.0831 (8)
H9A0.03860.41090.56170.125*
H9B0.20570.47930.60570.125*
H9C0.08430.39430.65720.125*
C100.4962 (4)0.45157 (19)0.74996 (14)0.0597 (5)
H10A0.56100.52090.76300.072*
H10B0.35760.46630.74300.072*
C110.9333 (3)0.3930 (2)1.20404 (14)0.0620 (6)
H11A0.81470.36101.17880.074*
C121.0879 (3)0.4242 (2)1.14197 (14)0.0604 (6)
H12A1.03400.48551.10880.072*
C131.2723 (5)0.4692 (3)1.18754 (18)0.0875 (9)
H13A1.30800.53851.16160.105*
H13B1.37840.41771.17880.105*
C141.2550 (5)0.4890 (3)1.28285 (19)0.0920 (10)
H14A1.36060.45071.31190.110*
H14B1.26920.56731.29420.110*
C151.0623 (5)0.4496 (3)1.31641 (16)0.0800 (8)
H15A1.04550.46111.37640.096*
C161.0091 (4)0.3322 (3)1.28420 (15)0.0737 (7)
C170.8967 (5)0.4939 (3)1.26053 (18)0.0884 (9)
H17A0.92450.56451.23460.106*
H17B0.76990.49421.28650.106*
C180.8353 (7)0.2817 (5)1.3307 (2)0.1257 (16)
H18A0.87570.26331.38680.189*
H18B0.79170.21621.30220.189*
H18C0.73050.33431.33220.189*
C191.1675 (6)0.2462 (3)1.2809 (2)0.0988 (11)
H19A1.27880.27621.25330.148*
H19B1.12010.18291.25050.148*
H19C1.20470.22451.33660.148*
C201.1400 (3)0.3334 (2)1.08030 (14)0.0637 (6)
H20A1.23280.36221.04090.076*
H20B1.20240.27311.11040.076*
C210.3935 (3)0.3035 (2)0.84428 (13)0.0548 (5)
C220.4577 (3)0.22560 (19)0.91276 (13)0.0540 (5)
C230.3379 (4)0.1377 (2)0.93392 (16)0.0700 (7)
H23A0.21800.12700.90680.084*
C240.4017 (5)0.0662 (3)0.99674 (19)0.0831 (8)
H24A0.32530.00631.01200.100*
C250.5781 (5)0.0851 (2)1.03575 (16)0.0756 (7)
H25A0.62380.03811.07770.091*
C260.6875 (4)0.17521 (19)1.01182 (13)0.0580 (5)
C270.8771 (4)0.2008 (2)1.05701 (14)0.0625 (6)
O30.9282 (3)0.42517 (19)0.87612 (13)0.0712 (5)
H310.970 (6)0.493 (4)0.871 (2)0.103 (12)*
H321.020 (6)0.384 (4)0.851 (2)0.111 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0609 (10)0.0502 (9)0.0449 (8)−0.0055 (8)0.0042 (7)−0.0049 (8)
N20.0580 (10)0.0596 (11)0.0496 (9)−0.0052 (9)−0.0080 (8)−0.0031 (8)
N30.0677 (11)0.0598 (11)0.0448 (9)0.0007 (10)−0.0059 (8)−0.0011 (9)
O10.0527 (8)0.0858 (12)0.0805 (11)−0.0020 (9)−0.0054 (8)−0.0119 (10)
O20.1293 (17)0.0611 (11)0.0760 (12)0.0033 (12)−0.0296 (11)0.0112 (10)
C10.0608 (11)0.0457 (10)0.0521 (10)0.0023 (10)−0.0015 (9)−0.0007 (9)
C20.0563 (11)0.0551 (12)0.0553 (11)−0.0027 (10)−0.0024 (9)−0.0011 (10)
C30.0943 (18)0.0577 (14)0.0651 (14)−0.0191 (14)−0.0012 (13)0.0020 (12)
C40.127 (2)0.0740 (17)0.0585 (14)−0.0293 (18)−0.0019 (15)0.0070 (13)
C50.1024 (19)0.0689 (16)0.0497 (12)−0.0215 (15)−0.0041 (12)−0.0041 (12)
C60.0670 (13)0.0535 (12)0.0584 (12)−0.0066 (11)−0.0102 (9)0.0019 (10)
C70.0846 (16)0.0659 (15)0.0711 (15)−0.0043 (13)0.0138 (13)−0.0193 (13)
C80.0909 (18)0.0741 (18)0.0846 (18)−0.0257 (16)−0.0117 (15)−0.0012 (15)
C90.0700 (15)0.0827 (18)0.096 (2)0.0101 (15)−0.0225 (14)−0.0004 (16)
C100.0726 (13)0.0508 (12)0.0553 (11)−0.0009 (11)−0.0083 (10)−0.0044 (10)
C110.0634 (13)0.0698 (15)0.0523 (11)0.0122 (11)−0.0061 (9)−0.0083 (11)
C120.0732 (14)0.0547 (13)0.0527 (11)0.0017 (11)−0.0121 (10)0.0028 (10)
C130.0916 (19)0.100 (2)0.0709 (16)−0.0322 (18)−0.0087 (14)−0.0056 (16)
C140.118 (2)0.088 (2)0.0689 (16)−0.0129 (19)−0.0287 (16)−0.0106 (15)
C150.105 (2)0.0843 (19)0.0502 (12)0.0075 (17)−0.0120 (12)−0.0118 (13)
C160.0944 (17)0.0774 (18)0.0491 (12)−0.0003 (15)−0.0076 (11)0.0035 (12)
C170.102 (2)0.092 (2)0.0702 (16)0.0267 (18)−0.0074 (14)−0.0248 (16)
C180.154 (3)0.151 (4)0.0734 (19)−0.040 (3)0.026 (2)0.006 (2)
C190.145 (3)0.0752 (19)0.0743 (17)0.023 (2)−0.0426 (19)0.0044 (16)
C200.0604 (12)0.0768 (17)0.0539 (11)0.0021 (12)−0.0013 (9)−0.0068 (12)
C210.0500 (11)0.0603 (12)0.0542 (11)−0.0010 (10)0.0036 (8)−0.0155 (10)
C220.0580 (12)0.0564 (12)0.0481 (10)−0.0066 (10)0.0098 (9)−0.0131 (9)
C230.0706 (15)0.0743 (16)0.0654 (14)−0.0205 (13)0.0127 (11)−0.0153 (13)
C240.101 (2)0.0730 (17)0.0755 (16)−0.0347 (16)0.0194 (15)0.0035 (14)
C250.108 (2)0.0615 (15)0.0573 (13)−0.0187 (15)0.0054 (13)0.0036 (12)
C260.0786 (14)0.0501 (11)0.0456 (10)−0.0036 (11)0.0059 (10)−0.0029 (9)
C270.0860 (16)0.0513 (12)0.0501 (11)0.0064 (12)−0.0031 (11)−0.0034 (10)
O30.0613 (10)0.0674 (12)0.0853 (12)−0.0080 (10)0.0110 (8)−0.0047 (10)
Geometric parameters (Å, °) top
N1—C221.337 (3)C11—C171.544 (4)
N1—C261.345 (3)C11—C161.559 (3)
N2—C211.325 (3)C11—H11A0.9800
N2—C101.459 (3)C12—C201.525 (4)
N2—H20.82 (2)C12—C131.545 (4)
N3—C271.318 (3)C12—H12A0.9800
N3—C201.461 (3)C13—C141.552 (4)
N3—H30.86 (3)C13—H13A0.9700
O1—C211.234 (3)C13—H13B0.9700
O2—C271.242 (3)C14—C151.512 (5)
C1—C21.524 (3)C14—H14A0.9700
C1—C71.537 (3)C14—H14B0.9700
C1—C61.564 (3)C15—C171.527 (4)
C1—H1A0.9800C15—C161.553 (4)
C2—C101.528 (3)C15—H15A0.9800
C2—C31.548 (3)C16—C191.506 (5)
C2—H2A0.9800C16—C181.543 (5)
C3—C41.562 (4)C17—H17A0.9700
C3—H3A0.9700C17—H17B0.9700
C3—H3B0.9700C18—H18A0.9600
C4—C51.502 (4)C18—H18B0.9600
C4—H4A0.9700C18—H18C0.9600
C4—H4B0.9700C19—H19A0.9600
C5—C71.526 (4)C19—H19B0.9600
C5—C61.548 (4)C19—H19C0.9600
C5—H5A0.9800C20—H20A0.9700
C6—C91.518 (4)C20—H20B0.9700
C6—C81.534 (4)C21—C221.505 (3)
C7—H7A0.9700C22—C231.390 (4)
C7—H7B0.9700C23—C241.391 (4)
C8—H8A0.9600C23—H23A0.9300
C8—H8B0.9600C24—C251.368 (4)
C8—H8C0.9600C24—H24A0.9300
C9—H9A0.9600C25—C261.382 (4)
C9—H9B0.9600C25—H25A0.9300
C9—H9C0.9600C26—C271.506 (3)
C10—H10A0.9700O3—H310.87 (5)
C10—H10B0.9700O3—H320.90 (4)
C11—C121.514 (4)
C22—N1—C26117.60 (19)C20—C12—C13111.1 (2)
C21—N2—C10123.8 (2)C11—C12—H12A106.5
C21—N2—H2119.2 (17)C20—C12—H12A106.5
C10—N2—H2116.9 (17)C13—C12—H12A106.5
C27—N3—C20122.3 (2)C12—C13—C14116.2 (3)
C27—N3—H3120.2 (17)C12—C13—H13A108.2
C20—N3—H3117.4 (17)C14—C13—H13A108.2
C2—C1—C7107.55 (19)C12—C13—H13B108.2
C2—C1—C6114.69 (18)C14—C13—H13B108.2
C7—C1—C687.32 (18)H13A—C13—H13B107.4
C2—C1—H1A114.7C15—C14—C13112.7 (2)
C7—C1—H1A114.7C15—C14—H14A109.1
C6—C1—H1A114.7C13—C14—H14A109.1
C1—C2—C10114.43 (19)C15—C14—H14B109.1
C1—C2—C3111.28 (17)C13—C14—H14B109.1
C10—C2—C3111.0 (2)H14A—C14—H14B107.8
C1—C2—H2A106.5C14—C15—C17108.9 (3)
C10—C2—H2A106.5C14—C15—C16111.8 (3)
C3—C2—H2A106.5C17—C15—C1687.8 (2)
C2—C3—C4115.1 (2)C14—C15—H15A115.1
C2—C3—H3A108.5C17—C15—H15A115.1
C4—C3—H3A108.5C16—C15—H15A115.1
C2—C3—H3B108.5C19—C16—C18107.8 (3)
C4—C3—H3B108.5C19—C16—C15118.8 (3)
H3A—C3—H3B107.5C18—C16—C15112.3 (3)
C5—C4—C3112.8 (2)C19—C16—C11121.7 (2)
C5—C4—H4A109.0C18—C16—C11109.7 (3)
C3—C4—H4A109.0C15—C16—C1185.0 (2)
C5—C4—H4B109.0C15—C17—C1186.4 (2)
C3—C4—H4B109.0C15—C17—H17A114.3
H4A—C4—H4B107.8C11—C17—H17A114.3
C4—C5—C7109.3 (2)C15—C17—H17B114.3
C4—C5—C6111.9 (2)C11—C17—H17B114.2
C7—C5—C688.31 (19)H17A—C17—H17B111.4
C4—C5—H5A114.8C16—C18—H18A109.5
C7—C5—H5A114.8C16—C18—H18B109.5
C6—C5—H5A114.8H18A—C18—H18B109.5
C9—C6—C8108.1 (2)C16—C18—H18C109.5
C9—C6—C5118.8 (2)H18A—C18—H18C109.5
C8—C6—C5112.2 (2)H18B—C18—H18C109.5
C9—C6—C1121.6 (2)C16—C19—H19A109.5
C8—C6—C1109.9 (2)C16—C19—H19B109.5
C5—C6—C184.67 (18)H19A—C19—H19B109.5
C5—C7—C186.32 (19)C16—C19—H19C109.5
C5—C7—H7A114.3H19A—C19—H19C109.5
C1—C7—H7A114.3H19B—C19—H19C109.5
C5—C7—H7B114.3N3—C20—C12112.38 (19)
C1—C7—H7B114.3N3—C20—H20A109.1
H7A—C7—H7B111.4C12—C20—H20A109.1
C6—C8—H8A109.5N3—C20—H20B109.1
C6—C8—H8B109.5C12—C20—H20B109.1
H8A—C8—H8B109.5H20A—C20—H20B107.9
C6—C8—H8C109.5O1—C21—N2124.4 (2)
H8A—C8—H8C109.5O1—C21—C22119.8 (2)
H8B—C8—H8C109.5N2—C21—C22115.86 (18)
C6—C9—H9A109.5N1—C22—C23122.9 (2)
C6—C9—H9B109.5N1—C22—C21117.59 (19)
H9A—C9—H9B109.5C23—C22—C21119.5 (2)
C6—C9—H9C109.5C22—C23—C24118.4 (2)
H9A—C9—H9C109.5C22—C23—H23A120.8
H9B—C9—H9C109.5C24—C23—H23A120.8
N2—C10—C2111.88 (19)C25—C24—C23119.2 (3)
N2—C10—H10A109.2C25—C24—H24A120.4
C2—C10—H10A109.2C23—C24—H24A120.4
N2—C10—H10B109.2C24—C25—C26118.9 (3)
C2—C10—H10B109.2C24—C25—H25A120.5
H10A—C10—H10B107.9C26—C25—H25A120.5
C12—C11—C17108.1 (2)N1—C26—C25123.0 (2)
C12—C11—C16115.7 (2)N1—C26—C27117.2 (2)
C17—C11—C1686.95 (19)C25—C26—C27119.7 (2)
C12—C11—H11A114.3O2—C27—N3123.5 (2)
C17—C11—H11A114.3O2—C27—C26119.6 (2)
C16—C11—H11A114.3N3—C27—C26116.9 (2)
C11—C12—C20114.9 (2)H31—O3—H32103 (4)
C11—C12—C13110.7 (2)
C7—C1—C2—C10−178.2 (2)C14—C15—C16—C18168.8 (3)
C6—C1—C2—C1086.5 (2)C17—C15—C16—C18−81.7 (3)
C7—C1—C2—C354.9 (3)C14—C15—C16—C11−81.9 (2)
C6—C1—C2—C3−40.3 (3)C17—C15—C16—C1127.6 (2)
C1—C2—C3—C4−10.1 (4)C12—C11—C16—C19−39.6 (4)
C10—C2—C3—C4−138.8 (3)C17—C11—C16—C19−148.2 (3)
C2—C3—C4—C57.6 (4)C12—C11—C16—C18−166.7 (3)
C3—C4—C5—C7−50.0 (4)C17—C11—C16—C1884.7 (3)
C3—C4—C5—C646.1 (4)C12—C11—C16—C1581.3 (3)
C4—C5—C6—C940.2 (3)C17—C11—C16—C15−27.3 (2)
C7—C5—C6—C9150.4 (2)C14—C15—C17—C1184.4 (3)
C4—C5—C6—C8167.5 (3)C16—C15—C17—C11−27.8 (2)
C7—C5—C6—C8−82.3 (2)C12—C11—C17—C15−88.3 (2)
C4—C5—C6—C1−83.1 (2)C16—C11—C17—C1527.7 (2)
C7—C5—C6—C127.07 (17)C27—N3—C20—C12−97.3 (3)
C2—C1—C6—C9−39.5 (3)C11—C12—C20—N355.0 (3)
C7—C1—C6—C9−147.6 (3)C13—C12—C20—N3−178.4 (2)
C2—C1—C6—C8−167.1 (2)C10—N2—C21—O1−4.0 (3)
C7—C1—C6—C884.8 (2)C10—N2—C21—C22175.63 (19)
C2—C1—C6—C581.2 (2)C26—N1—C22—C230.4 (3)
C7—C1—C6—C5−26.87 (18)C26—N1—C22—C21−179.78 (18)
C4—C5—C7—C185.2 (3)O1—C21—C22—N1−170.6 (2)
C6—C5—C7—C1−27.51 (18)N2—C21—C22—N19.8 (3)
C2—C1—C7—C5−87.9 (2)O1—C21—C22—C239.3 (3)
C6—C1—C7—C527.22 (18)N2—C21—C22—C23−170.4 (2)
C21—N2—C10—C2−95.3 (3)N1—C22—C23—C24−0.9 (4)
C1—C2—C10—N262.7 (2)C21—C22—C23—C24179.2 (2)
C3—C2—C10—N2−170.3 (2)C22—C23—C24—C250.5 (4)
C17—C11—C12—C20−179.3 (2)C23—C24—C25—C260.3 (4)
C16—C11—C12—C2085.2 (3)C22—N1—C26—C250.6 (3)
C17—C11—C12—C1353.8 (3)C22—N1—C26—C27−177.24 (19)
C16—C11—C12—C13−41.6 (3)C24—C25—C26—N1−0.9 (4)
C11—C12—C13—C14−8.2 (4)C24—C25—C26—C27176.8 (3)
C20—C12—C13—C14−137.1 (3)C20—N3—C27—O2−6.1 (4)
C12—C13—C14—C155.6 (5)C20—N3—C27—C26171.8 (2)
C13—C14—C15—C17−48.7 (4)N1—C26—C27—O2179.6 (2)
C13—C14—C15—C1646.6 (4)C25—C26—C27—O21.8 (3)
C14—C15—C16—C1941.7 (3)N1—C26—C27—N31.6 (3)
C17—C15—C16—C19151.2 (3)C25—C26—C27—N3−176.2 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O30.82 (2)2.16 (2)2.941 (3)160 (2)
N3—H3···O30.86 (3)2.19 (3)3.017 (3)159 (2)
O3—H31···O2i0.87 (5)1.90 (5)2.756 (3)167 (4)
O3—H32···O1ii0.90 (4)1.86 (5)2.754 (3)171 (3)
Symmetry codes: (i) −x+2, y+1/2, −z+2; (ii) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O30.82 (2)2.16 (2)2.941 (3)160 (2)
N3—H3···O30.86 (3)2.19 (3)3.017 (3)159 (2)
O3—H31···O2i0.87 (5)1.90 (5)2.756 (3)167 (4)
O3—H32···O1ii0.90 (4)1.86 (5)2.754 (3)171 (3)
Symmetry codes: (i) −x+2, y+1/2, −z+2; (ii) x+1, y, z.
Acknowledgements top

Partial support from VIEP–UAP (14/G/NAT/05) is acknowledged.

references
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