organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(2Z,6Z)-N2,N2′-Bis(2,6-diiso­propyl­phen­yl)-N1,N1′-bis­­(2-meth­oxy­ethyl)pyridine-2,6-dicarboxamidine

aOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, bÇanakkale Onsekiz Mart University, Arts and Sciences Faculty, Department of Chemistry, 17020 Çanakkale, Turkey, and cEge University, Science Faculty, Department of Chemistry, 35100 İzmir, Turkey
*Correspondence e-mail: namiko@omu.edu.tr

(Received 18 November 2007; accepted 1 December 2007; online 6 December 2007)

In the title compound, C37H53N5O2, the benzene rings make dihedral angles of 84.61 (8) and 67.10 (9)° with the pyridine ring. The crystal structure is stabilized by strong intra­molecular inter­actions. The two (2-methoxyethyl)amine groups are disordered over two positions; the site occupancies are ca 0.6 and 0.4.

Related literature

For related literature, see: Archer et al. (2006[Archer, A. M., Bouwkamp, M. W., Cortez, M. P., Lobkovsky, E. & Chirik, P. J. (2006). Organometallics, 25, 4269-4278.]); Bacha et al. (1987[Bacha, C., Ferreira, I., Loiseau, P., Schapoval, E., Tarayre, J. P. & Wolf, C. (1987). Pharm. Acta Helv. 62, 292-296.]); Bonnett (1970[Bonnett, R. (1970). The Chemistry of the Carbon-Nitrogen Double Bond, pp. 597-662. New York: Interscience.]); Shishkin et al. (2004[Shishkin, E. V., Vasil'ev, V. A. & Shishkin, V. E. (2004). Russ. J. Gen. Chem. 74, 475-476.]); Sladowska et al. (1995[Sladowska, H., Potoczek, J., Sieklucka-Dziuba, M., Semczuk, A. & Kleinrok, Z. (1995). Farmaco, 50, 761-768.]).

[Scheme 1]

Experimental

Crystal data
  • C37H53N5O2

  • Mr = 599.84

  • Monoclinic, P 21 /c

  • a = 9.8343 (6) Å

  • b = 21.4903 (10) Å

  • c = 17.8137 (10) Å

  • β = 105.561 (4)°

  • V = 3626.8 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.72 × 0.64 × 0.57 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.960, Tmax = 0.973

  • 27457 measured reflections

  • 7034 independent reflections

  • 4098 reflections with I > 2.0σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.199

  • S = 1.00

  • 7034 reflections

  • 489 parameters

  • 426 restraints

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2A—H2A1⋯N1 0.86 2.11 2.598 (4) 115
N4A—H4A1⋯O2A 0.86 2.33 2.735 (5) 110
N4A—H4A1⋯N1 0.86 2.29 2.688 (5) 109
C16—H16⋯N3 0.98 2.40 2.842 (4) 107

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

Imide functionality is found as a basic structural element in a wide range of naturally occurring compounds such as uracil and thymine. Moreover, many imide-containing unnatural products have been prepared to test the pharmacological properties as well as their structural properties (Bacha et al., 1987; Sladowska et al., 1995). Imidoyl chlorides react with carboxylic acids and their salts, yielding N-substitue imides with regard to Mumm rearrangement reaction (Bonnett, 1970; Shishkin et al., 2004). We describe here the crystal structure of the title compound as determined by an X-ray crystallographic analysis.

The structure of the title compound is shown in Fig. 1. The interatomic distances and angles show no anomalies. In the molecular structure of the title compound, (C10—C15) and (C26—C31) phenyl rings make dihedral angles of 84.61 (8) and 67.10 (9)°, respectively, with the pyridine ring. In the molecule, the two (2-methoxyethyl)amine groups, (N2/O1/C7—C9) and (N4/O2/C23—C25) were disordered over sites N2A/O1A/C7A–C9A; N4A/O2A/C23A—C25A and N2B/O1B/C7B–C9B; N4B/O2B/C23B—C25B, with site occupancy factors 59.7 (3) and 40.3 (3)%, respectively.

There are no significant inter-molecular interactions in the crystal structure of the title compound and the crystal structure is stabilizded by strong intramolecular interactions of the type N—H···N, N—H···O and C—H···N; details of these interactions have been provided in the Table.

Related literature top

For related literature, see: Archer et al. (2006); Bacha et al. (1987); Bonnett (1970); Shishkin et al. (2004); Sladowska et al. (1995).

Experimental top

The title compound was synthesized according to a modification of literature methods (Archer et al., 2006) and X-ray quality crystals were grown from CH2Cl2-hexane (1:2 v/v, 30 ml).

Refinement top

H atoms were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.96, 0.97, 0.98, 0.93 and 0.86 Å for CH3, CH2, CH, aromatic CH and NH groups, respectively. The displacement parameters of the H atoms were constrained as Uiso(H) = 1.2Ueq (1.5Ueq for methyl) of the parent atom. In the molecule, the two (2-methoxyethyl)amine groups, (N2/O1/C7—C9) and (N4/O2/C23—C25) show positional disorder and the refined site-occupancy factors of the disordered parts, viz. N2A/O1A/C7A–C9A/N4A/O2A/C23A—C25A and N2B/O1B/C7B–C9B/N4B/O2B/C23B—C25B, are 59.7 (3) and 40.3 (3)%, respectively. The disordered atoms were refined using the following restraints: SIMU, DELU and SADI (SHELXL; Sheldrick, 1997).

Structure description top

Imide functionality is found as a basic structural element in a wide range of naturally occurring compounds such as uracil and thymine. Moreover, many imide-containing unnatural products have been prepared to test the pharmacological properties as well as their structural properties (Bacha et al., 1987; Sladowska et al., 1995). Imidoyl chlorides react with carboxylic acids and their salts, yielding N-substitue imides with regard to Mumm rearrangement reaction (Bonnett, 1970; Shishkin et al., 2004). We describe here the crystal structure of the title compound as determined by an X-ray crystallographic analysis.

The structure of the title compound is shown in Fig. 1. The interatomic distances and angles show no anomalies. In the molecular structure of the title compound, (C10—C15) and (C26—C31) phenyl rings make dihedral angles of 84.61 (8) and 67.10 (9)°, respectively, with the pyridine ring. In the molecule, the two (2-methoxyethyl)amine groups, (N2/O1/C7—C9) and (N4/O2/C23—C25) were disordered over sites N2A/O1A/C7A–C9A; N4A/O2A/C23A—C25A and N2B/O1B/C7B–C9B; N4B/O2B/C23B—C25B, with site occupancy factors 59.7 (3) and 40.3 (3)%, respectively.

There are no significant inter-molecular interactions in the crystal structure of the title compound and the crystal structure is stabilizded by strong intramolecular interactions of the type N—H···N, N—H···O and C—H···N; details of these interactions have been provided in the Table.

For related literature, see: Archer et al. (2006); Bacha et al. (1987); Bonnett (1970); Shishkin et al. (2004); Sladowska et al. (1995).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A view of (II), with 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms have been omitted for clarity.
(2Z,6Z)-N2,N2'-Bis(2,6-diisopropylphenyl)- N1,N1'-bis(2-methoxyethyl)pyridine-2,6-dicarboxamidine top
Crystal data top
C37H53N5O2F(000) = 1304
Mr = 599.84Dx = 1.099 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 23890 reflections
a = 9.8343 (6) Åθ = 1.5–27.2°
b = 21.4903 (10) ŵ = 0.07 mm1
c = 17.8137 (10) ÅT = 296 K
β = 105.561 (4)°Prism, light yellow
V = 3626.8 (4) Å30.72 × 0.64 × 0.57 mm
Z = 4
Data collection top
STOE IPDS 2
diffractometer
7034 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus4098 reflections with I > 2.0σ(I)
Plane graphite monochromatorRint = 0.053
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.5°
w scansh = 1212
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2626
Tmin = 0.960, Tmax = 0.973l = 2120
27457 measured reflections
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)] = 0.062H-atom parameters constrained
wR(F2) = 0.199 w = 1/[σ2(Fo2) + (0.1212P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
7034 reflectionsΔρmax = 0.32 e Å3
489 parametersΔρmin = 0.28 e Å3
426 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0065 (15)
Crystal data top
C37H53N5O2V = 3626.8 (4) Å3
Mr = 599.84Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.8343 (6) ŵ = 0.07 mm1
b = 21.4903 (10) ÅT = 296 K
c = 17.8137 (10) Å0.72 × 0.64 × 0.57 mm
β = 105.561 (4)°
Data collection top
STOE IPDS 2
diffractometer
7034 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
4098 reflections with I > 2.0σ(I)
Tmin = 0.960, Tmax = 0.973Rint = 0.053
27457 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062426 restraints
wR(F2) = 0.199H-atom parameters constrained
S = 1.01Δρmax = 0.32 e Å3
7034 reflectionsΔρmin = 0.28 e Å3
489 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.5370 (5)0.7545 (2)0.4930 (3)0.0943 (14)0.597 (3)
O1B0.5298 (6)0.7640 (4)0.5321 (4)0.0925 (16)0.403 (3)
O2A0.5502 (5)0.72967 (16)0.7186 (3)0.0923 (13)0.597 (3)
O2B0.5425 (7)0.7151 (3)0.7689 (4)0.0951 (15)0.403 (3)
N10.2067 (2)0.64873 (8)0.54446 (12)0.0461 (5)
N2A0.2482 (4)0.7518 (2)0.4776 (4)0.0654 (14)0.597 (3)
H2A10.30270.72900.51270.078*0.597 (3)
N2B0.2535 (5)0.7427 (4)0.4586 (6)0.0632 (15)0.403 (3)
H2B10.31070.71300.47800.076*0.403 (3)
N30.0055 (2)0.75478 (9)0.40625 (13)0.0540 (6)
N4A0.4169 (5)0.6192 (2)0.6705 (4)0.0618 (14)0.597 (3)
H4A10.38440.65590.65720.074*0.597 (3)
N4B0.4298 (7)0.6165 (3)0.6539 (6)0.0631 (16)0.403 (3)
H4B10.40800.64980.62640.076*0.403 (3)
N50.3329 (2)0.51445 (9)0.65512 (13)0.0552 (6)
C10.1955 (2)0.59498 (10)0.58032 (14)0.0430 (5)
C20.0708 (3)0.56236 (11)0.56537 (15)0.0501 (6)
H2A0.06560.52490.59060.060*
C30.0458 (3)0.58608 (12)0.51249 (17)0.0586 (7)
H30.13160.56520.50230.070*
C40.0352 (3)0.64116 (12)0.47447 (16)0.0544 (7)
H4A0.11270.65760.43780.065*
C50.0930 (2)0.67107 (10)0.49226 (14)0.0451 (6)
C60.1146 (3)0.73043 (11)0.45166 (16)0.0517 (6)
C7A0.3149 (4)0.8061 (3)0.4565 (5)0.0731 (14)0.597 (3)
H7A10.31250.80400.40180.088*0.597 (3)
H7A20.26350.84300.46440.088*0.597 (3)
C8A0.4584 (5)0.8106 (2)0.5026 (4)0.0778 (13)0.597 (3)
H8A10.46080.81550.55710.093*0.597 (3)
H8A20.50250.84680.48680.093*0.597 (3)
C9A0.6721 (7)0.7599 (4)0.5508 (6)0.112 (2)0.597 (3)
H9A10.72830.72380.54850.168*0.597 (3)
H9A20.65720.76300.60180.168*0.597 (3)
H9A30.72020.79650.54050.168*0.597 (3)
C7B0.3184 (5)0.7976 (4)0.4383 (7)0.0720 (15)0.403 (3)
H7B10.28440.80400.38250.086*0.403 (3)
H7B20.28930.83310.46380.086*0.403 (3)
C8B0.4666 (6)0.7952 (4)0.4590 (5)0.0861 (15)0.403 (3)
H8B10.50280.83730.46210.103*0.403 (3)
H8B20.49620.77400.41790.103*0.403 (3)
C9B0.6630 (9)0.7389 (6)0.5238 (7)0.104 (3)0.403 (3)
H9B10.71320.71930.57160.155*0.403 (3)
H9B20.71920.77220.51190.155*0.403 (3)
H9B30.64430.70900.48230.155*0.403 (3)
C100.0038 (2)0.80692 (11)0.35734 (16)0.0508 (6)
C110.0518 (3)0.86324 (12)0.37645 (17)0.0573 (6)
C120.0666 (3)0.91245 (13)0.3238 (2)0.0662 (8)
H120.10220.95030.33540.079*
C130.0297 (3)0.90611 (14)0.2554 (2)0.0741 (9)
H130.03960.93960.22130.089*
C140.0219 (3)0.85041 (14)0.2370 (2)0.0705 (8)
H140.04550.84660.19000.085*
C150.0398 (3)0.79974 (12)0.28689 (17)0.0588 (7)
C160.0947 (3)0.86906 (14)0.4514 (2)0.0719 (8)
H160.12260.82730.46370.086*
C170.0252 (5)0.8880 (3)0.5181 (3)0.1348 (17)
H17A0.00650.89090.56450.202*
H17B0.06020.92780.50720.202*
H17C0.09920.85770.52560.202*
C180.2207 (4)0.9107 (2)0.4459 (3)0.1056 (12)
H18A0.24200.91190.49540.158*
H18B0.30050.89470.40700.158*
H18C0.19950.95200.43170.158*
C190.0930 (3)0.73796 (14)0.2644 (2)0.0711 (8)
H190.15300.71990.31240.085*
C200.1838 (5)0.7434 (2)0.2081 (3)0.1138 (14)
H20A0.25900.77240.22830.171*
H20B0.12720.75790.15860.171*
H20C0.22280.70340.20180.171*
C210.0254 (5)0.6931 (2)0.2344 (3)0.1140 (14)
H21A0.01160.65460.22080.171*
H21B0.09090.71030.18920.171*
H21C0.07300.68550.27410.171*
C220.3279 (3)0.57234 (10)0.63804 (15)0.0480 (6)
C23A0.5549 (5)0.6181 (2)0.7229 (5)0.0726 (14)0.597 (3)
H23A0.55820.58610.76160.087*0.597 (3)
H23B0.62210.60690.69400.087*0.597 (3)
C24A0.5971 (7)0.6758 (2)0.7617 (4)0.0842 (13)0.597 (3)
H24A0.56350.67680.80820.101*0.597 (3)
H24B0.69940.67680.77860.101*0.597 (3)
C25A0.5939 (11)0.7803 (3)0.7842 (5)0.114 (2)0.597 (3)
H25A0.56950.82080.76190.170*0.597 (3)
H25B0.69390.77830.80740.170*0.597 (3)
H25C0.54520.77280.82330.170*0.597 (3)
C23B0.5661 (6)0.6184 (3)0.7076 (8)0.0716 (15)0.403 (3)
H23C0.63180.59570.68580.086*0.403 (3)
H23D0.56230.59750.75530.086*0.403 (3)
C24B0.6177 (7)0.6806 (3)0.7259 (5)0.0820 (13)0.403 (3)
H24C0.71610.67860.75540.098*0.403 (3)
H24D0.61340.70250.67770.098*0.403 (3)
C25B0.5763 (15)0.7832 (3)0.7469 (7)0.103 (3)0.403 (3)
H25D0.52960.81250.77220.154*0.403 (3)
H25E0.54360.78860.69150.154*0.403 (3)
H25F0.67640.79010.76370.154*0.403 (3)
C260.4478 (3)0.48655 (11)0.71093 (16)0.0522 (6)
C270.4385 (3)0.48101 (12)0.78807 (17)0.0607 (7)
C280.5494 (4)0.45132 (14)0.84108 (19)0.0757 (9)
H280.54640.44750.89260.091*
C290.6624 (4)0.42760 (15)0.8198 (2)0.0853 (11)
H290.73570.40870.85670.102*
C300.6674 (3)0.43182 (14)0.7434 (2)0.0727 (9)
H300.74370.41480.72900.087*
C310.5608 (3)0.46091 (11)0.68764 (17)0.0574 (6)
C320.3120 (4)0.50400 (14)0.8115 (2)0.0720 (8)
H320.26950.53710.77480.086*
C330.3440 (6)0.5318 (2)0.8925 (3)0.1256 (16)
H33A0.41290.56430.89730.188*
H33B0.38030.50000.93040.188*
H33C0.25900.54880.90100.188*
C340.2035 (5)0.45314 (19)0.8025 (3)0.1180 (14)
H34A0.12300.46860.81740.177*
H34B0.24350.41860.83520.177*
H34C0.17500.43980.74910.177*
C350.5654 (3)0.46243 (13)0.60353 (18)0.0661 (7)
H350.50490.49690.57830.079*
C360.7109 (4)0.4741 (2)0.5927 (3)0.1046 (12)
H36A0.70540.47480.53810.157*
H36B0.77370.44140.61750.157*
H36C0.74590.51330.61570.157*
C370.5028 (5)0.40298 (18)0.5621 (2)0.0998 (12)
H37A0.50550.40470.50860.150*
H37B0.40670.39880.56420.150*
H37C0.55660.36790.58710.150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0658 (17)0.099 (2)0.109 (3)0.0041 (16)0.008 (2)0.004 (2)
O1B0.062 (2)0.099 (3)0.106 (3)0.004 (2)0.003 (2)0.015 (3)
O2A0.099 (2)0.0544 (16)0.099 (3)0.0028 (16)0.016 (2)0.0037 (17)
O2B0.095 (2)0.072 (2)0.099 (3)0.001 (2)0.008 (3)0.015 (2)
N10.0457 (11)0.0400 (10)0.0484 (13)0.0014 (8)0.0054 (9)0.0052 (8)
N2A0.0514 (16)0.0571 (19)0.077 (3)0.0094 (14)0.0007 (16)0.0296 (19)
N2B0.0511 (18)0.057 (2)0.074 (3)0.0046 (17)0.0046 (19)0.023 (2)
N30.0501 (12)0.0480 (11)0.0573 (14)0.0001 (9)0.0028 (10)0.0170 (10)
N4A0.0632 (18)0.0446 (15)0.062 (3)0.0025 (14)0.0096 (17)0.0073 (16)
N4B0.063 (2)0.049 (2)0.062 (3)0.0002 (17)0.009 (2)0.010 (2)
N50.0582 (13)0.0428 (11)0.0592 (15)0.0043 (9)0.0064 (10)0.0108 (10)
C10.0516 (13)0.0373 (11)0.0402 (14)0.0020 (9)0.0122 (10)0.0013 (9)
C20.0563 (15)0.0415 (12)0.0524 (16)0.0025 (10)0.0147 (12)0.0078 (11)
C30.0474 (14)0.0544 (15)0.0700 (19)0.0082 (11)0.0089 (13)0.0081 (13)
C40.0468 (14)0.0538 (14)0.0576 (17)0.0001 (11)0.0056 (12)0.0107 (12)
C50.0431 (13)0.0417 (12)0.0468 (15)0.0006 (9)0.0055 (10)0.0054 (10)
C60.0453 (12)0.0475 (12)0.0567 (16)0.0024 (10)0.0041 (11)0.0128 (11)
C7A0.0578 (16)0.064 (2)0.090 (3)0.0137 (15)0.0061 (17)0.024 (2)
C8A0.0589 (17)0.073 (2)0.094 (3)0.0154 (15)0.0068 (19)0.016 (2)
C9A0.070 (3)0.118 (5)0.134 (5)0.000 (3)0.002 (3)0.008 (4)
C7B0.0578 (18)0.064 (2)0.086 (3)0.0142 (18)0.0058 (19)0.023 (2)
C8B0.0647 (19)0.085 (2)0.101 (3)0.0122 (19)0.009 (2)0.020 (2)
C9B0.066 (4)0.103 (5)0.127 (6)0.001 (3)0.001 (4)0.011 (4)
C100.0416 (13)0.0486 (13)0.0556 (17)0.0012 (10)0.0015 (11)0.0161 (11)
C110.0503 (14)0.0513 (13)0.0623 (16)0.0022 (11)0.0013 (11)0.0085 (12)
C120.0653 (18)0.0471 (14)0.080 (2)0.0028 (12)0.0078 (15)0.0143 (14)
C130.082 (2)0.0601 (17)0.077 (2)0.0027 (15)0.0143 (17)0.0324 (16)
C140.0744 (19)0.0681 (19)0.067 (2)0.0023 (15)0.0164 (15)0.0235 (15)
C150.0530 (14)0.0589 (14)0.0616 (18)0.0010 (11)0.0101 (12)0.0171 (12)
C160.0779 (18)0.0651 (16)0.0686 (18)0.0024 (13)0.0126 (14)0.0033 (14)
C170.106 (3)0.206 (5)0.076 (3)0.009 (3)0.003 (2)0.024 (3)
C180.094 (2)0.128 (3)0.093 (3)0.023 (2)0.022 (2)0.008 (2)
C190.0732 (17)0.0620 (15)0.079 (2)0.0048 (13)0.0216 (14)0.0121 (13)
C200.125 (3)0.100 (3)0.139 (4)0.022 (2)0.074 (3)0.013 (2)
C210.094 (3)0.092 (2)0.151 (4)0.0075 (19)0.023 (3)0.028 (2)
C220.0543 (13)0.0417 (12)0.0447 (14)0.0034 (9)0.0076 (10)0.0039 (9)
C23A0.0672 (18)0.0554 (16)0.077 (3)0.0006 (16)0.0128 (18)0.0083 (17)
C24A0.0802 (18)0.0586 (15)0.089 (3)0.0011 (14)0.0197 (19)0.0062 (17)
C25A0.118 (4)0.086 (3)0.118 (5)0.010 (3)0.000 (4)0.041 (3)
C23B0.066 (2)0.0557 (19)0.076 (3)0.0016 (18)0.011 (2)0.0059 (19)
C24B0.0786 (18)0.0572 (15)0.087 (3)0.0007 (14)0.0177 (19)0.0056 (18)
C25B0.109 (5)0.069 (3)0.104 (6)0.007 (3)0.017 (5)0.028 (4)
C260.0591 (15)0.0381 (12)0.0544 (17)0.0035 (11)0.0063 (12)0.0089 (11)
C270.0772 (17)0.0425 (12)0.0599 (18)0.0056 (12)0.0142 (13)0.0072 (11)
C280.103 (3)0.0622 (17)0.055 (2)0.0127 (17)0.0093 (17)0.0108 (14)
C290.092 (2)0.074 (2)0.073 (3)0.0310 (18)0.0061 (19)0.0139 (17)
C300.073 (2)0.0632 (18)0.076 (2)0.0209 (14)0.0089 (16)0.0038 (15)
C310.0628 (15)0.0470 (13)0.0585 (15)0.0074 (11)0.0096 (12)0.0048 (11)
C320.0908 (19)0.0578 (15)0.0726 (19)0.0042 (13)0.0312 (16)0.0072 (13)
C330.140 (4)0.128 (3)0.117 (3)0.007 (3)0.048 (3)0.042 (3)
C340.110 (3)0.086 (2)0.172 (4)0.017 (2)0.064 (3)0.014 (2)
C350.0743 (17)0.0610 (15)0.0634 (17)0.0057 (13)0.0194 (14)0.0022 (13)
C360.094 (2)0.132 (3)0.096 (3)0.015 (2)0.041 (2)0.012 (2)
C370.128 (3)0.091 (2)0.076 (2)0.021 (2)0.020 (2)0.0139 (18)
Geometric parameters (Å, º) top
O1A—C9A1.452 (7)C16—C181.510 (5)
O1A—C8A1.465 (5)C16—H160.9800
O1B—C8B1.449 (6)C17—H17A0.9600
O1B—C9B1.461 (7)C17—H17B0.9600
O2A—C24A1.398 (5)C17—H17C0.9600
O2A—C25A1.570 (6)C18—H18A0.9600
O2B—C24B1.410 (6)C18—H18B0.9600
O2B—C25B1.574 (7)C18—H18C0.9600
N1—C51.337 (3)C19—C211.496 (5)
N1—C11.339 (3)C19—C201.515 (5)
N2A—C61.350 (4)C19—H190.9800
N2A—C7A1.438 (4)C20—H20A0.9600
N2A—H2A10.8600C20—H20B0.9600
N2B—C61.363 (4)C20—H20C0.9600
N2B—C7B1.433 (5)C21—H21A0.9600
N2B—H2B10.8600C21—H21B0.9600
N3—C61.271 (3)C21—H21C0.9600
N3—C101.417 (3)C23A—C24A1.426 (5)
N4A—C221.358 (4)C23A—H23A0.9700
N4A—C23A1.426 (4)C23A—H23B0.9700
N4A—H4A10.8600C24A—H24A0.9700
N4B—C221.354 (5)C24A—H24B0.9700
N4B—C23B1.423 (5)C25A—H25A0.9600
N4B—H4B10.8600C25A—H25B0.9600
N5—C221.279 (3)C25A—H25C0.9600
N5—C261.422 (3)C23B—C24B1.437 (6)
C1—C21.375 (3)C23B—H23C0.9700
C1—C221.507 (3)C23B—H23D0.9700
C2—C31.372 (4)C24B—H24C0.9700
C2—H2A0.9300C24B—H24D0.9700
C3—C41.381 (4)C25B—H25D0.9600
C3—H30.9300C25B—H25E0.9600
C4—C51.375 (3)C25B—H25F0.9600
C4—H4A0.9300C26—C311.399 (4)
C5—C61.509 (3)C26—C271.406 (4)
C7A—C8A1.433 (6)C27—C281.391 (4)
C7A—H7A10.9700C27—C321.498 (4)
C7A—H7A20.9700C28—C291.366 (5)
C8A—H8A10.9700C28—H280.9300
C8A—H8A20.9700C29—C301.378 (5)
C9A—H9A10.9600C29—H290.9300
C9A—H9A20.9600C30—C311.384 (4)
C9A—H9A30.9600C30—H300.9300
C7B—C8B1.405 (6)C31—C351.512 (4)
C7B—H7B10.9700C32—C341.506 (5)
C7B—H7B20.9700C32—C331.515 (5)
C8B—H8B10.9700C32—H320.9800
C8B—H8B20.9700C33—H33A0.9600
C9B—H9B10.9600C33—H33B0.9600
C9B—H9B20.9600C33—H33C0.9600
C9B—H9B30.9600C34—H34A0.9600
C10—C151.401 (4)C34—H34B0.9600
C10—C111.407 (4)C34—H34C0.9600
C11—C121.395 (4)C35—C361.515 (5)
C11—C161.510 (5)C35—C371.521 (5)
C12—C131.367 (5)C35—H350.9800
C12—H120.9300C36—H36A0.9600
C13—C141.374 (5)C36—H36B0.9600
C13—H130.9300C36—H36C0.9600
C14—C151.386 (4)C37—H37A0.9600
C14—H140.9300C37—H37B0.9600
C15—C191.520 (4)C37—H37C0.9600
C16—C171.488 (5)
C9A—O1A—C8A105.2 (5)C21—C19—C15111.6 (3)
C8B—O1B—C9B105.0 (5)C20—C19—C15114.4 (3)
C24A—O2A—C25A100.4 (4)C21—C19—H19106.5
C24B—O2B—C25B100.2 (5)C20—C19—H19106.5
C5—N1—C1118.8 (2)C15—C19—H19106.5
C6—N2A—C7A131.1 (4)C19—C20—H20A109.5
C6—N2A—H2A1114.5C19—C20—H20B109.5
C7A—N2A—H2A1114.5H20A—C20—H20B109.5
C6—N2B—C7B129.7 (5)C19—C20—H20C109.5
C6—N2B—H2B1115.1H20A—C20—H20C109.5
C7B—N2B—H2B1115.1H20B—C20—H20C109.5
C6—N3—C10125.9 (2)C19—C21—H21A109.5
C22—N4A—C23A131.1 (4)C19—C21—H21B109.5
C22—N4A—H4A1114.4H21A—C21—H21B109.5
C23A—N4A—H4A1114.4C19—C21—H21C109.5
C22—N4B—C23B132.1 (5)H21A—C21—H21C109.5
C22—N4B—H4B1114.0H21B—C21—H21C109.5
C23B—N4B—H4B1114.0N5—C22—N4B130.9 (4)
C22—N5—C26123.3 (2)N5—C22—N4A129.9 (3)
N1—C1—C2122.1 (2)N5—C22—C1116.5 (2)
N1—C1—C22115.9 (2)N4B—C22—C1111.8 (4)
C2—C1—C22122.0 (2)N4A—C22—C1113.0 (3)
C3—C2—C1118.8 (2)C24A—C23A—N4A113.9 (3)
C3—C2—H2A120.6C24A—C23A—H23A108.8
C1—C2—H2A120.6N4A—C23A—H23A108.8
C2—C3—C4119.7 (2)C24A—C23A—H23B108.8
C2—C3—H3120.1N4A—C23A—H23B108.8
C4—C3—H3120.1H23A—C23A—H23B107.7
C5—C4—C3118.2 (2)O2A—C24A—C23A116.3 (5)
C5—C4—H4A120.9O2A—C24A—H24A108.2
C3—C4—H4A120.9C23A—C24A—H24A108.2
N1—C5—C4122.5 (2)O2A—C24A—H24B108.2
N1—C5—C6116.0 (2)C23A—C24A—H24B108.2
C4—C5—C6121.5 (2)H24A—C24A—H24B107.4
N3—C6—N2A131.0 (3)O2A—C25A—H25A109.5
N3—C6—N2B129.2 (4)O2A—C25A—H25B109.5
N3—C6—C5116.7 (2)H25A—C25A—H25B109.5
N2A—C6—C5111.8 (3)O2A—C25A—H25C109.5
N2B—C6—C5112.7 (3)H25A—C25A—H25C109.5
C8A—C7A—N2A110.7 (3)H25B—C25A—H25C109.5
C8A—C7A—H7A1109.5N4B—C23B—C24B113.0 (4)
N2A—C7A—H7A1109.5N4B—C23B—H23C109.0
C8A—C7A—H7A2109.5C24B—C23B—H23C109.0
N2A—C7A—H7A2109.5N4B—C23B—H23D109.0
H7A1—C7A—H7A2108.1C24B—C23B—H23D109.0
C7A—C8A—O1A110.3 (4)H23C—C23B—H23D107.8
C7A—C8A—H8A1109.6O2B—C24B—C23B114.1 (6)
O1A—C8A—H8A1109.6O2B—C24B—H24C108.7
C7A—C8A—H8A2109.6C23B—C24B—H24C108.7
O1A—C8A—H8A2109.6O2B—C24B—H24D108.7
H8A1—C8A—H8A2108.1C23B—C24B—H24D108.7
O1A—C9A—H9A1109.5H24C—C24B—H24D107.6
O1A—C9A—H9A2109.5O2B—C25B—H25D109.5
H9A1—C9A—H9A2109.5O2B—C25B—H25E109.5
O1A—C9A—H9A3109.5H25D—C25B—H25E109.5
H9A1—C9A—H9A3109.5O2B—C25B—H25F109.5
H9A2—C9A—H9A3109.5H25D—C25B—H25F109.5
C8B—C7B—N2B113.8 (4)H25E—C25B—H25F109.5
C8B—C7B—H7B1108.8C31—C26—C27121.4 (2)
N2B—C7B—H7B1108.8C31—C26—N5120.3 (2)
C8B—C7B—H7B2108.8C27—C26—N5118.1 (2)
N2B—C7B—H7B2108.8C28—C27—C26117.3 (3)
H7B1—C7B—H7B2107.7C28—C27—C32121.4 (3)
C7B—C8B—O1B114.7 (5)C26—C27—C32121.3 (3)
C7B—C8B—H8B1108.6C29—C28—C27122.0 (3)
O1B—C8B—H8B1108.6C29—C28—H28119.0
C7B—C8B—H8B2108.6C27—C28—H28119.0
O1B—C8B—H8B2108.6C28—C29—C30119.8 (3)
H8B1—C8B—H8B2107.6C28—C29—H29120.1
O1B—C9B—H9B1109.5C30—C29—H29120.1
O1B—C9B—H9B2109.5C29—C30—C31121.1 (3)
H9B1—C9B—H9B2109.5C29—C30—H30119.4
O1B—C9B—H9B3109.5C31—C30—H30119.4
H9B1—C9B—H9B3109.5C30—C31—C26118.3 (3)
H9B2—C9B—H9B3109.5C30—C31—C35120.1 (3)
C15—C10—C11121.3 (2)C26—C31—C35121.5 (2)
C15—C10—N3120.0 (2)C27—C32—C34110.4 (3)
C11—C10—N3118.2 (2)C27—C32—C33114.8 (3)
C12—C11—C10117.8 (3)C34—C32—C33110.3 (4)
C12—C11—C16121.9 (3)C27—C32—H32107.0
C10—C11—C16120.3 (2)C34—C32—H32107.0
C13—C12—C11121.2 (3)C33—C32—H32107.0
C13—C12—H12119.4C32—C33—H33A109.5
C11—C12—H12119.4C32—C33—H33B109.5
C12—C13—C14120.2 (3)H33A—C33—H33B109.5
C12—C13—H13119.9C32—C33—H33C109.5
C14—C13—H13119.9H33A—C33—H33C109.5
C13—C14—C15121.5 (3)H33B—C33—H33C109.5
C13—C14—H14119.2C32—C34—H34A109.5
C15—C14—H14119.2C32—C34—H34B109.5
C14—C15—C10117.9 (3)H34A—C34—H34B109.5
C14—C15—C19120.7 (3)C32—C34—H34C109.5
C10—C15—C19121.4 (2)H34A—C34—H34C109.5
C17—C16—C11112.3 (3)H34B—C34—H34C109.5
C17—C16—C18110.5 (3)C31—C35—C36114.2 (3)
C11—C16—C18114.2 (3)C31—C35—C37110.3 (3)
C17—C16—H16106.4C36—C35—C37110.5 (3)
C11—C16—H16106.4C31—C35—H35107.1
C18—C16—H16106.4C36—C35—H35107.1
C16—C17—H17A109.5C37—C35—H35107.1
C16—C17—H17B109.5C35—C36—H36A109.5
H17A—C17—H17B109.5C35—C36—H36B109.5
C16—C17—H17C109.5H36A—C36—H36B109.5
H17A—C17—H17C109.5C35—C36—H36C109.5
H17B—C17—H17C109.5H36A—C36—H36C109.5
C16—C18—H18A109.5H36B—C36—H36C109.5
C16—C18—H18B109.5C35—C37—H37A109.5
H18A—C18—H18B109.5C35—C37—H37B109.5
C16—C18—H18C109.5H37A—C37—H37B109.5
H18A—C18—H18C109.5C35—C37—H37C109.5
H18B—C18—H18C109.5H37A—C37—H37C109.5
C21—C19—C20110.8 (4)H37B—C37—H37C109.5
C5—N1—C1—C20.3 (4)C10—C11—C16—C18145.9 (3)
C5—N1—C1—C22179.6 (2)C14—C15—C19—C2199.9 (4)
N1—C1—C2—C30.5 (4)C10—C15—C19—C2178.3 (4)
C22—C1—C2—C3179.5 (2)C14—C15—C19—C2026.8 (5)
C1—C2—C3—C41.2 (4)C10—C15—C19—C20155.0 (3)
C2—C3—C4—C51.0 (4)C26—N5—C22—N4B13.8 (8)
C1—N1—C5—C40.5 (4)C26—N5—C22—N4A6.0 (6)
C1—N1—C5—C6177.6 (2)C26—N5—C22—C1177.3 (2)
C3—C4—C5—N10.2 (4)C23B—N4B—C22—N515.7 (16)
C3—C4—C5—C6178.2 (3)C23B—N4B—C22—N4A77.2 (18)
C10—N3—C6—N2A14.4 (6)C23B—N4B—C22—C1175.0 (11)
C10—N3—C6—N2B8.1 (8)C23A—N4A—C22—N513.1 (11)
C10—N3—C6—C5173.9 (2)C23A—N4A—C22—N4B87 (2)
C7A—N2A—C6—N37.2 (10)C23A—N4A—C22—C1175.3 (7)
C7A—N2A—C6—N2B84.3 (16)N1—C1—C22—N5159.8 (2)
C7A—N2A—C6—C5179.3 (6)C2—C1—C22—N520.2 (4)
C7B—N2B—C6—N323.4 (14)N1—C1—C22—N4B11.2 (6)
C7B—N2B—C6—N2A79.6 (16)C2—C1—C22—N4B168.8 (6)
C7B—N2B—C6—C5170.3 (9)N1—C1—C22—N4A27.5 (5)
N1—C5—C6—N3174.9 (2)C2—C1—C22—N4A152.6 (4)
C4—C5—C6—N37.0 (4)C22—N4A—C23A—C24A162.2 (8)
N1—C5—C6—N2A1.6 (5)C25A—O2A—C24A—C23A170.5 (7)
C4—C5—C6—N2A179.7 (4)N4A—C23A—C24A—O2A35.4 (11)
N1—C5—C6—N2B17.0 (6)C22—N4B—C23B—C24B158.4 (11)
C4—C5—C6—N2B161.1 (6)C25B—O2B—C24B—C23B156.3 (7)
C6—N2A—C7A—C8A177.6 (7)N4B—C23B—C24B—O2B67.9 (12)
N2A—C7A—C8A—O1A57.8 (8)C22—N5—C26—C3191.5 (3)
C9A—O1A—C8A—C7A171.3 (7)C22—N5—C26—C2793.7 (3)
C6—N2B—C7B—C8B175.6 (11)C31—C26—C27—C282.7 (4)
N2B—C7B—C8B—O1B37.0 (14)N5—C26—C27—C28177.4 (2)
C9B—O1B—C8B—C7B152.0 (10)C31—C26—C27—C32175.1 (3)
C6—N3—C10—C1578.4 (4)N5—C26—C27—C320.3 (4)
C6—N3—C10—C11109.6 (3)C26—C27—C28—C290.8 (5)
C15—C10—C11—C121.6 (4)C32—C27—C28—C29177.0 (3)
N3—C10—C11—C12173.5 (2)C27—C28—C29—C301.2 (5)
C15—C10—C11—C16177.8 (2)C28—C29—C30—C311.3 (5)
N3—C10—C11—C165.9 (4)C29—C30—C31—C260.6 (5)
C10—C11—C12—C130.6 (4)C29—C30—C31—C35177.3 (3)
C16—C11—C12—C13178.8 (3)C27—C26—C31—C302.6 (4)
C11—C12—C13—C140.6 (5)N5—C26—C31—C30177.2 (2)
C12—C13—C14—C150.8 (5)C27—C26—C31—C35175.2 (2)
C13—C14—C15—C100.2 (4)N5—C26—C31—C350.6 (4)
C13—C14—C15—C19178.2 (3)C28—C27—C32—C3487.2 (4)
C11—C10—C15—C141.4 (4)C26—C27—C32—C3490.4 (4)
N3—C10—C15—C14173.1 (2)C28—C27—C32—C3338.3 (4)
C11—C10—C15—C19176.9 (2)C26—C27—C32—C33144.1 (3)
N3—C10—C15—C195.2 (4)C30—C31—C35—C3640.5 (4)
C12—C11—C16—C1793.3 (4)C26—C31—C35—C36141.7 (3)
C10—C11—C16—C1787.2 (4)C30—C31—C35—C3784.7 (4)
C12—C11—C16—C1833.5 (4)C26—C31—C35—C3793.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A1···N10.862.112.598 (4)115
N4A—H4A1···O2A0.862.332.735 (5)110
N4A—H4A1···N10.862.292.688 (5)109
C16—H16···N30.982.402.842 (4)107

Experimental details

Crystal data
Chemical formulaC37H53N5O2
Mr599.84
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.8343 (6), 21.4903 (10), 17.8137 (10)
β (°) 105.561 (4)
V3)3626.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.72 × 0.64 × 0.57
Data collection
DiffractometerSTOE IPDS 2
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.960, 0.973
No. of measured, independent and
observed [I > 2.0σ(I)] reflections
27457, 7034, 4098
Rint0.053
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.199, 1.01
No. of reflections7034
No. of parameters489
No. of restraints426
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.28

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A1···N10.862.112.598 (4)115.1
N4A—H4A1···O2A0.862.332.735 (5)109.5
N4A—H4A1···N10.862.292.688 (5)108.7
C16—H16···N30.982.402.842 (4)106.8
 

Acknowledgements

This study was supported financially by the Research Center of Ondokuz Mayıs University (project No. F-425).

References

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