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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-3-[(Di­methyl­amino)­methyl­­idene]-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one

aLaboratoire de Chimie Moléculaire, Département de Chimie, Faculté des Sciences-Semlalia, BP 2390, Université Cadi Ayyad, 40001, Marrakech, Morocco, bDepartment of Chemistry, University of Aveiro, CICECO, 3810-193, Aveiro, Portugal, cLaboratoire de Matériaux et Cristallochimie, Faculté des Sciences de Tunis, Université de Tunis ElManar, 2092 ElManar II, Tunis, Tunisia, and dEquipe de Chimie des Matériaux et de l'Environnement, FSTG-Marrakech, Université Cadi Ayyad, Bd Abdelkrim Khattabi, BP. 549, Marrakech, Morocco
*Correspondence e-mail: eh_soumhi@yahoo.fr

(Received 26 December 2013; accepted 28 December 2013; online 11 January 2014)

The asymmetric unit of the title compound, C18H17N3O, consists of two independent mol­ecules, each having an E conformation with respect to the C=C bond between the benzodiazepinone and di­methyl­amine groups. In the crystal, the two independent mol­ecules are linked into a dimer by a pair of N—H⋯O hydrogen bonds.

Related literature

For background to natural benzodiazepines and their properties, see: Di Braccio et al. (2001[Di Braccio, M., Grossi, G., Roma, G., Vargiu, L., Mura, M. & Marongiu, M. E. (2001). Eur. J. Med. Chem. 36, 935-949.]); Kavita et al. (1988[Kavita, D. T., Achaiah, G. & Reddy, V. M. (1988). J. Indian Chem. Soc. 65, 567-570.]). For the synthesis, see: Nardi et al. (1973[Nardi, D., Tajana, A. & Rossi, S. (1973). J. Heterocycl. Chem. 10, 815-819.]). For a related structure, see: Loughzail et al. (2014[Loughzail, M., Baouid, A., Almeida Paz, F. A., Cavaleiro, J. A. S. & Soumhi, E. H. (2014). Acta Cryst. E70, o32.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17N3O

  • Mr = 291.35

  • Monoclinic, P 21 /n

  • a = 11.281 (2) Å

  • b = 14.005 (4) Å

  • c = 20.124 (3) Å

  • β = 95.97 (1)°

  • V = 3162.1 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 300 K

  • 0.3 × 0.15 × 0.1 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.521, Tmax = 0.992

  • 8620 measured reflections

  • 6879 independent reflections

  • 3575 reflections with I > 2σ(I)

  • Rint = 0.034

  • 2 standard reflections every 60 min intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.158

  • S = 1.01

  • 6879 reflections

  • 402 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—HN1⋯O2i 0.86 2.17 2.861 (2) 137
N4—HN4⋯O1ii 0.86 2.41 2.939 (2) 121
Symmetry codes: (i) x+1, y+1, z; (ii) x-1, y-1, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990[Fair, C. K. (1990). MolEN. Enraf-Nonius, Delft, The Netherlands.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

The benzodiazepine nucleus is a pharmacophoric scaffold and represents a class of heterocycles with a wide range of applications. In particular, several representative benzodiazepines possess significant biological activity as antiviral (Di Braccio et al., 2001), antipsychotic agents (Kavita et al., 1988) and may be considered support for the synthesis of more active heterocyclic systems. Research in this area is highly active being directed towards the synthesis of compounds with enhanced pharmacological activity. Following the research efforts from some of us concerning novel synthetic pathways of new benzodiazepines (Loughzail et al., 2014).

The reaction of N,N-dimethylformamide dimethylacetal (DMF-DMA) in 4-phenyl-1H-1,5-benzodiazepin-2(3H)-one (Nardi et al., 1973) at reflux leads to the formation of the title compound, (E)-3-[(dimethylamino)methylene]-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one with a good yield of 75%. The main geometric feature determined by X-ray diffraction is in good agreement with that observed in a similar compound (Loughzail et al., 2014).

Related literature top

For background to natural benzodiazepines and their properties, see: Di Braccio et al. (2001); Kavita et al. (1988). For the synthesis, see: Nardi et al. (1973). For a related structure, see: Loughzail et al. (2014).

Experimental top

A mixture of 0.47 g (1.98 mmol) of 4-phenyl-1H-1,5-benzodiazepin-2(3H)-one in 4.5 ml of dimethylformamide-dimethylacetal (DMF-DMA) was stirred at 100 °C for 4 h and then cooled to ambient temperature. Filtration and washing with a little cold diethyl ether gave 0.46 g of (E)-3-[(dimethylamino)methylene]-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one. The product obtained was recrystallized from diethyl ether. Yield: 75%. Melting point: 497–498 K. 1H NMR (CDCl3, 300 MHz): δ 2.55 (s, 6H, (CH3)2N), 2.80 (s, 1H, NH), 6.32 (s, 1H, C=CH—N), 7.04–7.92 (m, 9H, H—Ar); 13C NMR (CDCl3, 75 MHz): δ 43.50 (N(CH3)2), 98.02 (C=), 121.47–141.86 (12 C-Ar), 151.18 (CH—N(CH3)2), 167.40 (Ph—C=N), 178.57 (CO). MS (m/z, %): 292 ([M+H]+.

Refinement top

All H-atoms were located in a difference map and then refined using a riding model with N—H = 0.86 Å and C—H = 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(N, C) or 1.5Ueq(Cmethyl).

Structure description top

The benzodiazepine nucleus is a pharmacophoric scaffold and represents a class of heterocycles with a wide range of applications. In particular, several representative benzodiazepines possess significant biological activity as antiviral (Di Braccio et al., 2001), antipsychotic agents (Kavita et al., 1988) and may be considered support for the synthesis of more active heterocyclic systems. Research in this area is highly active being directed towards the synthesis of compounds with enhanced pharmacological activity. Following the research efforts from some of us concerning novel synthetic pathways of new benzodiazepines (Loughzail et al., 2014).

The reaction of N,N-dimethylformamide dimethylacetal (DMF-DMA) in 4-phenyl-1H-1,5-benzodiazepin-2(3H)-one (Nardi et al., 1973) at reflux leads to the formation of the title compound, (E)-3-[(dimethylamino)methylene]-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one with a good yield of 75%. The main geometric feature determined by X-ray diffraction is in good agreement with that observed in a similar compound (Loughzail et al., 2014).

For background to natural benzodiazepines and their properties, see: Di Braccio et al. (2001); Kavita et al. (1988). For the synthesis, see: Nardi et al. (1973). For a related structure, see: Loughzail et al. (2014).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecule structure of the title compound with 50% probability ellipsoids.
(E)-3-[(Dimethylamino)methylidene]-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one top
Crystal data top
C18H17N3OF(000) = 1232
Mr = 291.35Dx = 1.224 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 11.281 (2) Åθ = 10–15°
b = 14.005 (4) ŵ = 0.08 mm1
c = 20.124 (3) ÅT = 300 K
β = 95.97 (1)°Prism, colourless
V = 3162.1 (12) Å30.3 × 0.15 × 0.1 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
3575 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 27.0°, θmin = 2.0°
ω/2θ scansh = 142
Absorption correction: ψ scan
(North et al., 1968)
k = 117
Tmin = 0.521, Tmax = 0.992l = 2525
8620 measured reflections2 standard reflections every 60 min
6879 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.158 w = 1/[σ2(Fo2) + (0.0688P)2 + 0.4349P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
6879 reflectionsΔρmax = 0.29 e Å3
402 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.016 (2)
Crystal data top
C18H17N3OV = 3162.1 (12) Å3
Mr = 291.35Z = 8
Monoclinic, P21/nMo Kα radiation
a = 11.281 (2) ŵ = 0.08 mm1
b = 14.005 (4) ÅT = 300 K
c = 20.124 (3) Å0.3 × 0.15 × 0.1 mm
β = 95.97 (1)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
3575 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.034
Tmin = 0.521, Tmax = 0.9922 standard reflections every 60 min
8620 measured reflections intensity decay: 1%
6879 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.01Δρmax = 0.29 e Å3
6879 reflectionsΔρmin = 0.23 e Å3
402 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*/Ueq
O10.87561 (14)0.89599 (11)0.18529 (8)0.0622 (4)
O20.10910 (14)0.10731 (12)0.31490 (8)0.0642 (4)
N10.90374 (15)0.78432 (12)0.26535 (9)0.0539 (5)
HN10.97960.79230.26770.065*
N20.74209 (15)0.62029 (12)0.23855 (9)0.0511 (4)
N30.51730 (17)0.83342 (15)0.14714 (10)0.0680 (6)
N40.08974 (16)0.00488 (14)0.23437 (10)0.0601 (5)
HN40.01450.01090.23710.072*
N50.28648 (17)0.14261 (13)0.24917 (10)0.0567 (5)
N60.47471 (16)0.10080 (14)0.32360 (10)0.0585 (5)
C10.83674 (18)0.82566 (15)0.21290 (11)0.0486 (5)
C20.85993 (18)0.72976 (14)0.31600 (11)0.0486 (5)
C30.9039 (2)0.75029 (17)0.38144 (12)0.0652 (6)
H30.96010.79860.38980.078*
C40.8659 (3)0.7007 (2)0.43365 (13)0.0836 (9)
H40.89570.71550.47730.100*
C50.7829 (3)0.6283 (2)0.42131 (14)0.0809 (8)
H50.75470.59570.45670.097*
C60.7425 (2)0.60485 (16)0.35695 (12)0.0623 (6)
H60.68930.55440.34920.075*
C70.77890 (18)0.65458 (14)0.30303 (11)0.0477 (5)
C80.71591 (17)0.67685 (15)0.18894 (11)0.0469 (5)
C90.71974 (18)0.78242 (14)0.19149 (10)0.0477 (5)
C100.6341 (2)0.84542 (16)0.16682 (11)0.0549 (6)
H100.66110.90770.16290.066*
C110.4533 (2)0.7461 (2)0.15408 (15)0.0837 (8)
H1110.49670.70660.18720.126*
H2110.44430.71310.11210.126*
H3110.37610.76020.16760.126*
C120.4456 (3)0.9158 (2)0.12312 (16)0.0989 (10)
H1120.49550.97130.12340.148*
H2120.38400.92640.15180.148*
H3120.41020.90380.07840.148*
C130.68919 (18)0.63175 (15)0.12197 (11)0.0512 (5)
C140.6549 (2)0.53721 (17)0.11563 (13)0.0635 (6)
H140.64370.50180.15360.076*
C150.6372 (2)0.4951 (2)0.05380 (15)0.0791 (8)
H150.61510.43120.05030.095*
C160.6517 (2)0.5463 (2)0.00301 (14)0.0776 (8)
H160.63820.51740.04470.093*
C170.6853 (3)0.6380 (2)0.00206 (14)0.0797 (8)
H170.69580.67270.03630.096*
C180.7045 (2)0.68149 (18)0.06404 (12)0.0703 (7)
H180.72810.74510.06680.084*
C190.15585 (18)0.04443 (15)0.28393 (11)0.0500 (5)
C200.13736 (19)0.04637 (15)0.17907 (11)0.0531 (5)
C210.0847 (2)0.02598 (18)0.11569 (13)0.0697 (7)
H210.01780.01310.11060.084*
C220.1294 (3)0.0624 (2)0.06001 (14)0.0822 (8)
H220.09420.04650.01760.099*
C230.2269 (3)0.1228 (2)0.06716 (14)0.0815 (8)
H230.25840.14670.02960.098*
C240.2770 (2)0.14734 (18)0.13008 (13)0.0701 (7)
H240.34050.19000.13470.084*
C250.2344 (2)0.10956 (15)0.18699 (12)0.0539 (6)
C260.31176 (18)0.08457 (15)0.29803 (11)0.0497 (5)
C270.28278 (18)0.01887 (14)0.29681 (10)0.0467 (5)
C280.35540 (19)0.09421 (15)0.31387 (10)0.0499 (5)
H280.31560.15120.31990.060*
C290.5536 (2)0.0227 (2)0.31182 (14)0.0718 (7)
H1290.57440.01120.35280.108*
H2290.51420.01990.27930.108*
H3290.62450.04740.29550.108*
C300.5312 (2)0.19260 (19)0.33861 (13)0.0728 (7)
H1300.58940.18630.37670.109*
H2300.56950.21380.30080.109*
H3300.47190.23840.34820.109*
C310.3668 (2)0.12737 (16)0.36159 (11)0.0536 (6)
C320.3746 (2)0.07799 (18)0.42135 (12)0.0730 (7)
H320.34460.01620.42230.088*
C330.4262 (3)0.1191 (2)0.47966 (14)0.0976 (11)
H330.42930.08540.51960.117*
C340.4727 (3)0.2090 (2)0.47906 (15)0.1087 (12)
H340.50810.23640.51830.130*
C350.4668 (3)0.2583 (2)0.42020 (15)0.1003 (11)
H350.49870.31940.41960.120*
C360.4145 (3)0.21896 (18)0.36220 (13)0.0740 (7)
H360.41070.25390.32270.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0509 (9)0.0479 (8)0.0874 (11)0.0082 (7)0.0046 (8)0.0143 (8)
O20.0491 (9)0.0686 (10)0.0742 (11)0.0202 (8)0.0027 (8)0.0177 (9)
N10.0366 (9)0.0559 (11)0.0683 (12)0.0045 (8)0.0019 (8)0.0091 (9)
N20.0454 (10)0.0447 (10)0.0626 (12)0.0035 (8)0.0027 (8)0.0017 (9)
N30.0468 (12)0.0712 (13)0.0834 (15)0.0108 (10)0.0054 (10)0.0044 (11)
N40.0365 (9)0.0664 (12)0.0765 (13)0.0051 (9)0.0013 (9)0.0148 (10)
N50.0551 (11)0.0481 (10)0.0658 (12)0.0115 (9)0.0012 (9)0.0047 (9)
N60.0420 (10)0.0619 (12)0.0709 (12)0.0019 (9)0.0032 (9)0.0023 (10)
C10.0413 (11)0.0409 (11)0.0644 (14)0.0021 (10)0.0093 (10)0.0022 (10)
C20.0438 (11)0.0425 (11)0.0600 (13)0.0008 (10)0.0077 (10)0.0005 (10)
C30.0710 (16)0.0593 (14)0.0645 (16)0.0153 (13)0.0033 (12)0.0046 (12)
C40.110 (2)0.0819 (19)0.0580 (16)0.0237 (18)0.0056 (15)0.0044 (14)
C50.106 (2)0.0754 (18)0.0628 (17)0.0220 (17)0.0155 (15)0.0092 (14)
C60.0689 (16)0.0502 (13)0.0682 (16)0.0122 (12)0.0097 (12)0.0038 (12)
C70.0445 (12)0.0385 (11)0.0603 (14)0.0037 (9)0.0061 (10)0.0010 (10)
C80.0345 (10)0.0446 (11)0.0613 (13)0.0015 (9)0.0042 (9)0.0022 (10)
C90.0408 (11)0.0446 (11)0.0576 (13)0.0010 (10)0.0041 (9)0.0019 (10)
C100.0491 (13)0.0514 (13)0.0639 (14)0.0027 (10)0.0044 (11)0.0032 (11)
C110.0438 (14)0.102 (2)0.104 (2)0.0068 (15)0.0016 (13)0.0067 (17)
C120.0777 (19)0.103 (2)0.110 (2)0.0393 (18)0.0192 (17)0.0020 (19)
C130.0387 (11)0.0495 (12)0.0645 (14)0.0028 (10)0.0011 (10)0.0013 (11)
C140.0614 (15)0.0550 (14)0.0714 (16)0.0099 (12)0.0057 (12)0.0020 (12)
C150.082 (2)0.0627 (16)0.089 (2)0.0123 (15)0.0093 (16)0.0156 (15)
C160.0734 (18)0.087 (2)0.0711 (18)0.0075 (16)0.0034 (14)0.0215 (16)
C170.092 (2)0.0838 (19)0.0646 (17)0.0135 (17)0.0120 (15)0.0045 (15)
C180.0849 (19)0.0615 (15)0.0653 (16)0.0156 (14)0.0109 (13)0.0039 (13)
C190.0417 (11)0.0479 (12)0.0600 (13)0.0059 (10)0.0034 (10)0.0004 (11)
C200.0448 (12)0.0485 (12)0.0648 (14)0.0028 (10)0.0006 (10)0.0104 (11)
C210.0643 (15)0.0639 (15)0.0769 (18)0.0145 (13)0.0126 (13)0.0119 (13)
C220.092 (2)0.0830 (19)0.0667 (17)0.0213 (17)0.0142 (15)0.0137 (15)
C230.091 (2)0.085 (2)0.0670 (17)0.0198 (17)0.0016 (15)0.0234 (15)
C240.0685 (16)0.0655 (16)0.0743 (17)0.0169 (13)0.0026 (13)0.0227 (13)
C250.0505 (13)0.0431 (11)0.0670 (15)0.0024 (10)0.0001 (11)0.0091 (11)
C260.0404 (11)0.0474 (12)0.0619 (14)0.0084 (10)0.0082 (10)0.0004 (11)
C270.0399 (11)0.0450 (11)0.0546 (12)0.0071 (9)0.0023 (9)0.0016 (9)
C280.0465 (12)0.0484 (12)0.0544 (13)0.0078 (10)0.0034 (10)0.0024 (10)
C290.0438 (13)0.0841 (18)0.0881 (18)0.0093 (13)0.0100 (12)0.0039 (15)
C300.0660 (16)0.0797 (18)0.0723 (16)0.0218 (14)0.0058 (13)0.0049 (14)
C310.0510 (13)0.0514 (13)0.0596 (14)0.0110 (10)0.0118 (10)0.0028 (11)
C320.092 (2)0.0630 (16)0.0647 (16)0.0243 (15)0.0117 (14)0.0000 (13)
C330.142 (3)0.094 (2)0.0561 (16)0.041 (2)0.0066 (17)0.0020 (15)
C340.158 (3)0.103 (2)0.0644 (18)0.064 (2)0.0082 (19)0.0160 (17)
C350.144 (3)0.0776 (19)0.080 (2)0.058 (2)0.013 (2)0.0136 (16)
C360.0922 (19)0.0621 (15)0.0684 (16)0.0279 (15)0.0123 (14)0.0016 (13)
Geometric parameters (Å, º) top
O1—C11.234 (2)C14—C151.372 (3)
O2—C191.229 (2)C14—H140.9300
N1—C11.362 (3)C15—C161.373 (4)
N1—C21.404 (3)C15—H150.9300
N1—HN10.8600C16—C171.341 (4)
N2—C81.285 (3)C16—H160.9300
N2—C71.405 (3)C17—C181.385 (3)
N3—C101.346 (3)C17—H170.9300
N3—C111.434 (3)C18—H180.9300
N3—C121.462 (3)C19—C271.473 (3)
N4—C191.369 (3)C20—C211.380 (3)
N4—C201.410 (3)C20—C251.404 (3)
N4—HN40.8600C21—C221.374 (4)
N5—C261.285 (3)C21—H210.9300
N5—C251.404 (3)C22—C231.383 (4)
N6—C281.343 (3)C22—H220.9300
N6—C291.445 (3)C23—C241.375 (3)
N6—C301.452 (3)C23—H230.9300
C1—C91.475 (3)C24—C251.392 (3)
C2—C31.388 (3)C24—H240.9300
C2—C71.401 (3)C26—C271.485 (3)
C3—C41.365 (3)C26—C311.488 (3)
C3—H30.9300C27—C281.358 (3)
C4—C51.385 (4)C28—H280.9300
C4—H40.9300C29—H1290.9600
C5—C61.368 (3)C29—H2290.9600
C5—H50.9300C29—H3290.9600
C6—C71.387 (3)C30—H1300.9600
C6—H60.9300C30—H2300.9600
C8—C91.480 (3)C30—H3300.9600
C8—C131.490 (3)C31—C321.382 (3)
C9—C101.364 (3)C31—C361.390 (3)
C10—H100.9300C32—C331.381 (4)
C11—H1110.9600C32—H320.9300
C11—H2110.9600C33—C341.364 (4)
C11—H3110.9600C33—H330.9300
C12—H1120.9600C34—C351.366 (4)
C12—H2120.9600C34—H340.9300
C12—H3120.9600C35—C361.368 (4)
C13—C141.381 (3)C35—H350.9300
C13—C181.384 (3)C36—H360.9300
C1—N1—C2125.81 (18)C15—C16—H16120.2
C1—N1—HN1117.1C16—C17—C18120.4 (3)
C2—N1—HN1117.1C16—C17—H17119.8
C8—N2—C7121.94 (18)C18—C17—H17119.8
C10—N3—C11124.4 (2)C13—C18—C17121.0 (2)
C10—N3—C12119.3 (2)C13—C18—H18119.5
C11—N3—C12116.0 (2)C17—C18—H18119.5
C19—N4—C20124.02 (18)O2—C19—N4120.08 (19)
C19—N4—HN4118.0O2—C19—C27123.1 (2)
C20—N4—HN4118.0N4—C19—C27116.86 (18)
C26—N5—C25120.83 (18)C21—C20—C25119.4 (2)
C28—N6—C29123.3 (2)C21—C20—N4118.8 (2)
C28—N6—C30120.1 (2)C25—C20—N4121.8 (2)
C29—N6—C30116.09 (19)C22—C21—C20121.2 (2)
O1—C1—N1119.60 (19)C22—C21—H21119.4
O1—C1—C9123.0 (2)C20—C21—H21119.4
N1—C1—C9117.35 (18)C21—C22—C23119.8 (3)
C3—C2—C7119.6 (2)C21—C22—H22120.1
C3—C2—N1117.26 (19)C23—C22—H22120.1
C7—C2—N1123.1 (2)C24—C23—C22119.6 (3)
C4—C3—C2121.0 (2)C24—C23—H23120.2
C4—C3—H3119.5C22—C23—H23120.2
C2—C3—H3119.5C23—C24—C25121.3 (2)
C3—C4—C5119.7 (2)C23—C24—H24119.4
C3—C4—H4120.2C25—C24—H24119.4
C5—C4—H4120.2C24—C25—C20118.6 (2)
C6—C5—C4119.9 (2)C24—C25—N5117.4 (2)
C6—C5—H5120.0C20—C25—N5123.9 (2)
C4—C5—H5120.0N5—C26—C27125.0 (2)
C5—C6—C7121.5 (2)N5—C26—C31116.26 (19)
C5—C6—H6119.2C27—C26—C31118.60 (19)
C7—C6—H6119.2C28—C27—C19113.94 (18)
C6—C7—C2118.2 (2)C28—C27—C26128.89 (19)
C6—C7—N2117.88 (19)C19—C27—C26116.65 (18)
C2—C7—N2123.59 (19)N6—C28—C27131.3 (2)
N2—C8—C9125.8 (2)N6—C28—H28114.4
N2—C8—C13116.74 (18)C27—C28—H28114.4
C9—C8—C13117.21 (19)N6—C29—H129109.5
C10—C9—C1114.81 (18)N6—C29—H229109.5
C10—C9—C8128.1 (2)H129—C29—H229109.5
C1—C9—C8116.25 (18)N6—C29—H329109.5
N3—C10—C9131.4 (2)H129—C29—H329109.5
N3—C10—H10114.3H229—C29—H329109.5
C9—C10—H10114.3N6—C30—H130109.5
N3—C11—H111109.5N6—C30—H230109.5
N3—C11—H211109.5H130—C30—H230109.5
H111—C11—H211109.5N6—C30—H330109.5
N3—C11—H311109.5H130—C30—H330109.5
H111—C11—H311109.5H230—C30—H330109.5
H211—C11—H311109.5C32—C31—C36117.7 (2)
N3—C12—H112109.5C32—C31—C26121.9 (2)
N3—C12—H212109.5C36—C31—C26120.4 (2)
H112—C12—H212109.5C33—C32—C31120.9 (2)
N3—C12—H312109.5C33—C32—H32119.5
H112—C12—H312109.5C31—C32—H32119.5
H212—C12—H312109.5C34—C33—C32120.4 (3)
C14—C13—C18117.6 (2)C34—C33—H33119.8
C14—C13—C8121.2 (2)C32—C33—H33119.8
C18—C13—C8121.1 (2)C33—C34—C35119.3 (3)
C15—C14—C13120.5 (2)C33—C34—H34120.3
C15—C14—H14119.7C35—C34—H34120.3
C13—C14—H14119.7C34—C35—C36121.0 (3)
C14—C15—C16120.8 (3)C34—C35—H35119.5
C14—C15—H15119.6C36—C35—H35119.5
C16—C15—H15119.6C35—C36—C31120.7 (2)
C17—C16—C15119.6 (3)C35—C36—H36119.6
C17—C16—H16120.2C31—C36—H36119.6
C2—N1—C1—O1155.3 (2)C20—N4—C19—O2152.1 (2)
C2—N1—C1—C925.2 (3)C20—N4—C19—C2727.3 (3)
C1—N1—C2—C3133.3 (2)C19—N4—C20—C21128.2 (2)
C1—N1—C2—C749.3 (3)C19—N4—C20—C2553.5 (3)
C7—C2—C3—C42.5 (4)C25—C20—C21—C223.5 (4)
N1—C2—C3—C4179.9 (2)N4—C20—C21—C22178.2 (2)
C2—C3—C4—C50.5 (4)C20—C21—C22—C231.8 (4)
C3—C4—C5—C62.1 (5)C21—C22—C23—C241.2 (4)
C4—C5—C6—C72.7 (4)C22—C23—C24—C252.6 (4)
C5—C6—C7—C20.6 (4)C23—C24—C25—C200.9 (4)
C5—C6—C7—N2174.1 (2)C23—C24—C25—N5176.5 (2)
C3—C2—C7—C62.0 (3)C21—C20—C25—C242.1 (3)
N1—C2—C7—C6179.4 (2)N4—C20—C25—C24179.7 (2)
C3—C2—C7—N2171.1 (2)C21—C20—C25—N5173.2 (2)
N1—C2—C7—N26.3 (3)N4—C20—C25—N55.0 (3)
C8—N2—C7—C6144.1 (2)C26—N5—C25—C24138.0 (2)
C8—N2—C7—C242.8 (3)C26—N5—C25—C2046.6 (3)
C7—N2—C8—C90.2 (3)C25—N5—C26—C274.4 (3)
C7—N2—C8—C13174.40 (18)C25—N5—C26—C31179.93 (19)
O1—C1—C9—C1033.0 (3)O2—C19—C27—C2835.1 (3)
N1—C1—C9—C10147.5 (2)N4—C19—C27—C28144.2 (2)
O1—C1—C9—C8137.2 (2)O2—C19—C27—C26137.4 (2)
N1—C1—C9—C842.3 (3)N4—C19—C27—C2643.3 (3)
N2—C8—C9—C10130.9 (2)N5—C26—C27—C28129.4 (3)
C13—C8—C9—C1054.6 (3)C31—C26—C27—C2855.0 (3)
N2—C8—C9—C160.4 (3)N5—C26—C27—C1959.4 (3)
C13—C8—C9—C1114.2 (2)C31—C26—C27—C19116.1 (2)
C11—N3—C10—C95.8 (4)C29—N6—C28—C275.0 (4)
C12—N3—C10—C9179.3 (3)C30—N6—C28—C27176.9 (2)
C1—C9—C10—N3174.9 (2)C19—C27—C28—N6173.6 (2)
C8—C9—C10—N316.2 (4)C26—C27—C28—N615.0 (4)
N2—C8—C13—C1421.1 (3)N5—C26—C31—C32165.7 (2)
C9—C8—C13—C14163.9 (2)C27—C26—C31—C3210.3 (3)
N2—C8—C13—C18155.1 (2)N5—C26—C31—C3615.5 (3)
C9—C8—C13—C1819.9 (3)C27—C26—C31—C36168.6 (2)
C18—C13—C14—C150.1 (4)C36—C31—C32—C331.0 (4)
C8—C13—C14—C15176.3 (2)C26—C31—C32—C33179.9 (3)
C13—C14—C15—C160.8 (4)C31—C32—C33—C341.2 (5)
C14—C15—C16—C171.0 (4)C32—C33—C34—C350.6 (6)
C15—C16—C17—C180.5 (4)C33—C34—C35—C360.3 (6)
C14—C13—C18—C170.4 (4)C34—C35—C36—C310.5 (5)
C8—C13—C18—C17176.8 (2)C32—C31—C36—C350.1 (4)
C16—C17—C18—C130.2 (4)C26—C31—C36—C35179.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O2i0.862.172.861 (2)137
N4—HN4···O1ii0.862.412.939 (2)121
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O2i0.862.172.861 (2)137
N4—HN4···O1ii0.862.412.939 (2)121
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y1, z.
 

References

First citationDi Braccio, M., Grossi, G., Roma, G., Vargiu, L., Mura, M. & Marongiu, M. E. (2001). Eur. J. Med. Chem. 36, 935–949.  Web of Science CrossRef PubMed CAS Google Scholar
First citationEnraf–Nonius (1989). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationFair, C. K. (1990). MolEN. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationKavita, D. T., Achaiah, G. & Reddy, V. M. (1988). J. Indian Chem. Soc. 65, 567–570.  Google Scholar
First citationLoughzail, M., Baouid, A., Almeida Paz, F. A., Cavaleiro, J. A. S. & Soumhi, E. H. (2014). Acta Cryst. E70, o32.  CSD CrossRef IUCr Journals Google Scholar
First citationNardi, D., Tajana, A. & Rossi, S. (1973). J. Heterocycl. Chem. 10, 815–819.  CrossRef CAS Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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