organic compounds
(E)-3-[(Dimethylamino)methylidene]-4-phenyl-1-(prop-2-ynyl)-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, cDepartment of Chemistry, University of Aveiro, QOPNA, 3810-193 Aveiro, Portugal, 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
The title compound, C21H19N3O, exhibits an E configuration with respect to the C=C bond between the benzodiazepine and trimethylamine groups. The seven-membered diazepine ring displays a boat conformation. In the crystal, molecules are linked by a C—H⋯O hydrogen bond, forming a chain along [110].
CCDC reference: 975297
Related literature
For benzodiazepine derivatives, see: Di Braccio et al. (2001); Pevarello et al. (1993). For related structures, see: Loughzail et al. (2011); Boudina et al. (2006).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2005); data reduction: SAINT; 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).
Supporting information
CCDC reference: 975297
https://doi.org/10.1107/S1600536813032960/is5319sup1.cif
contains datablocks I, HasRB. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032960/is5319Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813032960/is5319Isup3.cml
A mixture of 0.6 g (2.06 mmol) of 3-[(dimethylamino)methylene]-4-phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one, 0.26 g (1.14 mmol) of benzyltriethylammonium chloride and 3 ml of a 50% sodium hydroxide aqueous solution in benzene (25 ml) was stirred at ambient temperature. After 15 min, propagyl bromide was added slowly. After 8 h of stirring at 298 K, the reaction mixture was diluted with water (30 ml). The organic layer was extracted with benzene (3× 10 ml), dried over anhydrous sodium sulfate and evaporated under vacuum. The title compound was isolated by
on silica gel using hexane/ethyl acetate as The solid product was recrystallized in dichloromethane to give yellow crystals of the title compound.Yield: 93%, m.p. 488–490 K. 1H NMR (300 MHz, CDCl3): δ 2.36 (t, J = 2.27 Hz, 1H, HC≡C), 2.58 (s, 6H, (CH3)2N), 4.21 and 4.29 (AB system, d, J = 17.9 Hz, 2H, N—CH2—C), 6.46 (s, 1H, C=CH—N), 7.15–8.11 (9H, Ar—H). 13C NMR (75 MHz, CDCl3): δ 37.1 (1 C, N—CH2—C), 42.6 (N(CH3)2), 71.9 (1 C, HC≡C), 78.5 (1 C, HC≡C), 97.8 (C-3), 120.9–140.9 (Ar—C, =CH), 164.8 (1 C, Ph—C=N), 169 (1 C, CO).
All H-atoms were located in a difference map and refined using a riding model with C—H = 0.93–0.97 Å, and with Uiso = 1.2Ueq(C).
The benzodiazepine nucleus is extremely important, as it is the base of several drugs and other biologically active compounds with different properties. A large number of structurally modified benzodiazepines have been prepared and evaluated concerning their biological activity (Di Braccio et al., 2001; Pevarello et al., 1993) and may be considered support for the synthesis of more active heterocyclic systems. In this class of compounds, our research team is interested in the synthesis of novel benzodiazepines derived (Loughzail et al., 2011; Boudina et al., 2006). Here we wish to report the synthesis via phase transfer catalysis and the crystallographic studies of the title compound. The title compound was prepared by action of propargyl bromide with 3-dimethylaminomethylene-4-phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one using a catalytic amount of benzyltriethylammonium chloride (TBA-Cl) and sodium hydroxide aqueous solution in benzene. The obtained compound was typically characterized by 1H, 13C NMR, IR and
and the stereochemistry (E) of the benzodiazepine was determined by X-ray diffraction. The main geometric feature of the title compound is in good agreement with that observed in a similar compound (Loughzail et al., 2011).For benzodiazepine derivatives, see: Di Braccio et al. (2001); Pevarello et al. (1993). For related structures, see: Loughzail et al. (2011); Boudina et al. (2006).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).C21H19N3O | F(000) = 1392 |
Mr = 329.39 | Dx = 1.243 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 12.8122 (10) Å | θ = 10–15° |
b = 13.9317 (12) Å | µ = 0.08 mm−1 |
c = 19.7795 (14) Å | T = 300 K |
β = 94.647 (3)° | Block, yellow |
V = 3519.0 (5) Å3 | 0.13 × 0.10 × 0.08 mm |
Z = 8 |
Bruker X8 KappaCCD APEXII diffractometer | 3220 independent reflections |
Radiation source: fine-focus sealed tube | 2555 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω and φ scans | θmax = 25.4°, θmin = 3.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.990, Tmax = 0.994 | k = −16→13 |
21544 measured reflections | l = −23→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0423P)2 + 1.6343P] where P = (Fo2 + 2Fc2)/3 |
3220 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C21H19N3O | V = 3519.0 (5) Å3 |
Mr = 329.39 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 12.8122 (10) Å | µ = 0.08 mm−1 |
b = 13.9317 (12) Å | T = 300 K |
c = 19.7795 (14) Å | 0.13 × 0.10 × 0.08 mm |
β = 94.647 (3)° |
Bruker X8 KappaCCD APEXII diffractometer | 3220 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2555 reflections with I > 2σ(I) |
Tmin = 0.990, Tmax = 0.994 | Rint = 0.032 |
21544 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.16 e Å−3 |
3220 reflections | Δρmin = −0.14 e Å−3 |
228 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.23744 (12) | −0.00078 (11) | 0.47258 (7) | 0.0493 (4) | |
H1A | 0.1759 | −0.0412 | 0.4656 | 0.059* | |
H1B | 0.2886 | −0.0345 | 0.5026 | 0.059* | |
C2 | 0.20897 (11) | 0.08866 (12) | 0.50454 (8) | 0.0500 (4) | |
C3 | 0.18446 (14) | 0.15873 (15) | 0.53145 (9) | 0.0687 (5) | |
H3 | 0.1649 | 0.2146 | 0.5529 | 0.082* | |
C4 | 0.27086 (11) | −0.06084 (10) | 0.36193 (7) | 0.0418 (3) | |
C5 | 0.30050 (10) | −0.04291 (10) | 0.29321 (7) | 0.0387 (3) | |
C6 | 0.27571 (10) | 0.05269 (10) | 0.26392 (7) | 0.0396 (3) | |
C7 | 0.19842 (11) | 0.05802 (11) | 0.20333 (7) | 0.0449 (4) | |
C8 | 0.20304 (13) | 0.13347 (11) | 0.15770 (8) | 0.0545 (4) | |
H8 | 0.2563 | 0.1788 | 0.1638 | 0.065* | |
C9 | 0.12883 (16) | 0.14127 (14) | 0.10342 (9) | 0.0710 (5) | |
H9 | 0.1331 | 0.1913 | 0.0726 | 0.085* | |
C10 | 0.04882 (16) | 0.07593 (18) | 0.09453 (10) | 0.0811 (6) | |
H10 | −0.0017 | 0.0823 | 0.0583 | 0.097* | |
C11 | 0.04357 (15) | 0.00075 (17) | 0.13950 (11) | 0.0806 (6) | |
H11 | −0.0107 | −0.0436 | 0.1336 | 0.097* | |
C12 | 0.11855 (13) | −0.00900 (13) | 0.19330 (9) | 0.0603 (4) | |
H12 | 0.1155 | −0.0606 | 0.2229 | 0.072* | |
C13 | 0.37939 (11) | 0.13592 (10) | 0.34662 (7) | 0.0418 (3) | |
C14 | 0.46264 (12) | 0.20107 (11) | 0.34809 (9) | 0.0555 (4) | |
H14 | 0.4713 | 0.2385 | 0.3100 | 0.067* | |
C15 | 0.53236 (12) | 0.21109 (13) | 0.40479 (10) | 0.0630 (5) | |
H15 | 0.5886 | 0.2532 | 0.4043 | 0.076* | |
C16 | 0.51758 (12) | 0.15823 (13) | 0.46185 (9) | 0.0598 (4) | |
H16 | 0.5634 | 0.1653 | 0.5005 | 0.072* | |
C17 | 0.43540 (11) | 0.09509 (11) | 0.46209 (8) | 0.0497 (4) | |
H17 | 0.4257 | 0.0605 | 0.5013 | 0.060* | |
C18 | 0.36619 (10) | 0.08181 (10) | 0.40482 (7) | 0.0396 (3) | |
C19 | 0.33035 (10) | −0.12223 (10) | 0.25861 (7) | 0.0418 (3) | |
H19 | 0.3208 | −0.1804 | 0.2803 | 0.050* | |
C20 | 0.40194 (12) | −0.04771 (12) | 0.16008 (8) | 0.0537 (4) | |
H20A | 0.4630 | −0.0639 | 0.1374 | 0.064* | |
H20B | 0.4175 | 0.0056 | 0.1900 | 0.064* | |
H20C | 0.3460 | −0.0306 | 0.1271 | 0.064* | |
C21 | 0.39525 (14) | −0.22348 (12) | 0.17186 (9) | 0.0653 (5) | |
H21A | 0.4697 | −0.2296 | 0.1706 | 0.078* | |
H21B | 0.3620 | −0.2300 | 0.1268 | 0.078* | |
H21C | 0.3701 | −0.2727 | 0.2004 | 0.078* | |
N1 | 0.28111 (9) | 0.01576 (8) | 0.40710 (6) | 0.0415 (3) | |
N2 | 0.30977 (9) | 0.13373 (8) | 0.28823 (6) | 0.0446 (3) | |
N3 | 0.37076 (9) | −0.12945 (9) | 0.19895 (6) | 0.0462 (3) | |
O1 | 0.23521 (10) | −0.13715 (8) | 0.38040 (6) | 0.0660 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0566 (9) | 0.0513 (9) | 0.0418 (8) | −0.0016 (7) | 0.0155 (7) | 0.0015 (7) |
C2 | 0.0463 (8) | 0.0615 (10) | 0.0434 (8) | 0.0012 (7) | 0.0107 (6) | −0.0030 (8) |
C3 | 0.0633 (10) | 0.0749 (13) | 0.0700 (12) | 0.0078 (9) | 0.0182 (9) | −0.0209 (10) |
C4 | 0.0450 (7) | 0.0363 (8) | 0.0452 (8) | −0.0025 (6) | 0.0109 (6) | 0.0006 (6) |
C5 | 0.0420 (7) | 0.0362 (7) | 0.0384 (7) | −0.0030 (6) | 0.0065 (6) | −0.0013 (6) |
C6 | 0.0440 (7) | 0.0383 (8) | 0.0377 (7) | −0.0002 (6) | 0.0114 (6) | −0.0005 (6) |
C7 | 0.0484 (8) | 0.0449 (8) | 0.0421 (8) | 0.0077 (7) | 0.0078 (6) | −0.0031 (6) |
C8 | 0.0659 (10) | 0.0487 (9) | 0.0493 (9) | 0.0135 (8) | 0.0064 (7) | 0.0002 (7) |
C9 | 0.0899 (14) | 0.0705 (12) | 0.0518 (10) | 0.0326 (11) | 0.0009 (9) | 0.0031 (9) |
C10 | 0.0723 (13) | 0.1024 (17) | 0.0650 (12) | 0.0292 (12) | −0.0170 (10) | −0.0110 (12) |
C11 | 0.0597 (11) | 0.0990 (17) | 0.0804 (14) | −0.0018 (11) | −0.0105 (10) | −0.0117 (13) |
C12 | 0.0547 (9) | 0.0672 (11) | 0.0585 (10) | −0.0035 (8) | 0.0013 (8) | −0.0025 (8) |
C13 | 0.0461 (8) | 0.0360 (8) | 0.0448 (8) | −0.0011 (6) | 0.0122 (6) | −0.0075 (6) |
C14 | 0.0625 (9) | 0.0452 (9) | 0.0621 (10) | −0.0125 (7) | 0.0257 (8) | −0.0110 (8) |
C15 | 0.0442 (8) | 0.0583 (11) | 0.0880 (13) | −0.0119 (8) | 0.0155 (8) | −0.0270 (10) |
C16 | 0.0444 (8) | 0.0629 (11) | 0.0711 (11) | 0.0035 (8) | −0.0023 (8) | −0.0188 (9) |
C17 | 0.0486 (8) | 0.0495 (9) | 0.0508 (9) | 0.0080 (7) | 0.0017 (7) | −0.0060 (7) |
C18 | 0.0390 (7) | 0.0369 (7) | 0.0440 (8) | 0.0019 (6) | 0.0098 (6) | −0.0055 (6) |
C19 | 0.0438 (7) | 0.0373 (8) | 0.0449 (8) | −0.0043 (6) | 0.0078 (6) | −0.0009 (6) |
C20 | 0.0531 (9) | 0.0621 (10) | 0.0480 (9) | −0.0015 (7) | 0.0166 (7) | 0.0018 (8) |
C21 | 0.0720 (11) | 0.0573 (11) | 0.0690 (11) | −0.0003 (9) | 0.0213 (9) | −0.0224 (9) |
N1 | 0.0481 (6) | 0.0402 (7) | 0.0375 (6) | −0.0046 (5) | 0.0121 (5) | −0.0020 (5) |
N2 | 0.0569 (7) | 0.0367 (7) | 0.0415 (7) | −0.0019 (5) | 0.0111 (5) | 0.0003 (5) |
N3 | 0.0501 (7) | 0.0442 (7) | 0.0458 (7) | −0.0024 (5) | 0.0138 (6) | −0.0082 (6) |
O1 | 0.0993 (9) | 0.0428 (6) | 0.0605 (7) | −0.0180 (6) | 0.0342 (6) | −0.0033 (5) |
C1—C2 | 1.457 (2) | C12—H12 | 0.9300 |
C1—N1 | 1.4700 (18) | C13—C18 | 1.398 (2) |
C1—H1A | 0.9700 | C13—C14 | 1.399 (2) |
C1—H1B | 0.9700 | C13—N2 | 1.4012 (18) |
C2—C3 | 1.167 (2) | C14—C15 | 1.383 (2) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—O1 | 1.2244 (16) | C15—C16 | 1.373 (3) |
C4—N1 | 1.3911 (18) | C15—H15 | 0.9300 |
C4—C5 | 1.4622 (19) | C16—C17 | 1.372 (2) |
C5—C19 | 1.3705 (19) | C16—H16 | 0.9300 |
C5—C6 | 1.4767 (19) | C17—C18 | 1.393 (2) |
C6—N2 | 1.2893 (17) | C17—H17 | 0.9300 |
C6—C7 | 1.493 (2) | C18—N1 | 1.4301 (17) |
C7—C12 | 1.388 (2) | C19—N3 | 1.3303 (18) |
C7—C8 | 1.390 (2) | C19—H19 | 0.9300 |
C8—C9 | 1.380 (2) | C20—N3 | 1.4482 (19) |
C8—H8 | 0.9300 | C20—H20A | 0.9600 |
C9—C10 | 1.372 (3) | C20—H20B | 0.9600 |
C9—H9 | 0.9300 | C20—H20C | 0.9600 |
C10—C11 | 1.379 (3) | C21—N3 | 1.4590 (19) |
C10—H10 | 0.9300 | C21—H21A | 0.9600 |
C11—C12 | 1.381 (2) | C21—H21B | 0.9600 |
C11—H11 | 0.9300 | C21—H21C | 0.9600 |
C2—C1—N1 | 112.02 (12) | C15—C14—C13 | 121.58 (16) |
C2—C1—H1A | 109.2 | C15—C14—H14 | 119.2 |
N1—C1—H1A | 109.2 | C13—C14—H14 | 119.2 |
C2—C1—H1B | 109.2 | C16—C15—C14 | 119.29 (15) |
N1—C1—H1B | 109.2 | C16—C15—H15 | 120.4 |
H1A—C1—H1B | 107.9 | C14—C15—H15 | 120.4 |
C3—C2—C1 | 177.97 (17) | C17—C16—C15 | 120.23 (15) |
C2—C3—H3 | 180.0 | C17—C16—H16 | 119.9 |
O1—C4—N1 | 119.51 (13) | C15—C16—H16 | 119.9 |
O1—C4—C5 | 123.84 (13) | C16—C17—C18 | 121.35 (15) |
N1—C4—C5 | 116.61 (12) | C16—C17—H17 | 119.3 |
C19—C5—C4 | 115.50 (12) | C18—C17—H17 | 119.3 |
C19—C5—C6 | 126.24 (12) | C17—C18—C13 | 119.11 (13) |
C4—C5—C6 | 117.07 (11) | C17—C18—N1 | 119.76 (13) |
N2—C6—C5 | 126.02 (12) | C13—C18—N1 | 121.10 (12) |
N2—C6—C7 | 115.98 (12) | N3—C19—C5 | 130.42 (13) |
C5—C6—C7 | 117.85 (12) | N3—C19—H19 | 114.8 |
C12—C7—C8 | 119.06 (14) | C5—C19—H19 | 114.8 |
C12—C7—C6 | 120.98 (13) | N3—C20—H20A | 109.5 |
C8—C7—C6 | 119.89 (14) | N3—C20—H20B | 109.5 |
C9—C8—C7 | 120.13 (17) | H20A—C20—H20B | 109.5 |
C9—C8—H8 | 119.9 | N3—C20—H20C | 109.5 |
C7—C8—H8 | 119.9 | H20A—C20—H20C | 109.5 |
C10—C9—C8 | 120.55 (18) | H20B—C20—H20C | 109.5 |
C10—C9—H9 | 119.7 | N3—C21—H21A | 109.5 |
C8—C9—H9 | 119.7 | N3—C21—H21B | 109.5 |
C9—C10—C11 | 119.76 (18) | H21A—C21—H21B | 109.5 |
C9—C10—H10 | 120.1 | N3—C21—H21C | 109.5 |
C11—C10—H10 | 120.1 | H21A—C21—H21C | 109.5 |
C10—C11—C12 | 120.28 (19) | H21B—C21—H21C | 109.5 |
C10—C11—H11 | 119.9 | C4—N1—C18 | 120.39 (11) |
C12—C11—H11 | 119.9 | C4—N1—C1 | 115.01 (11) |
C11—C12—C7 | 120.19 (18) | C18—N1—C1 | 118.30 (11) |
C11—C12—H12 | 119.9 | C6—N2—C13 | 120.00 (12) |
C7—C12—H12 | 119.9 | C19—N3—C20 | 123.73 (12) |
C18—C13—C14 | 118.40 (14) | C19—N3—C21 | 120.29 (13) |
C18—C13—N2 | 123.75 (12) | C20—N3—C21 | 115.74 (12) |
C14—C13—N2 | 117.69 (13) | ||
O1—C4—C5—C19 | −27.5 (2) | C16—C17—C18—C13 | −1.7 (2) |
N1—C4—C5—C19 | 154.90 (12) | C16—C17—C18—N1 | −179.66 (13) |
O1—C4—C5—C6 | 140.80 (15) | C14—C13—C18—C17 | 0.53 (19) |
N1—C4—C5—C6 | −36.78 (17) | N2—C13—C18—C17 | −174.84 (12) |
C19—C5—C6—N2 | −133.01 (15) | C14—C13—C18—N1 | 178.43 (12) |
C4—C5—C6—N2 | 60.09 (18) | N2—C13—C18—N1 | 3.1 (2) |
C19—C5—C6—C7 | 51.59 (19) | C4—C5—C19—N3 | −172.74 (14) |
C4—C5—C6—C7 | −115.32 (14) | C6—C5—C19—N3 | 20.2 (2) |
N2—C6—C7—C12 | −146.20 (14) | O1—C4—N1—C18 | 146.04 (14) |
C5—C6—C7—C12 | 29.67 (19) | C5—C4—N1—C18 | −36.26 (18) |
N2—C6—C7—C8 | 30.81 (19) | O1—C4—N1—C1 | −5.6 (2) |
C5—C6—C7—C8 | −153.32 (13) | C5—C4—N1—C1 | 172.08 (12) |
C12—C7—C8—C9 | 0.2 (2) | C17—C18—N1—C4 | −121.72 (14) |
C6—C7—C8—C9 | −176.90 (14) | C13—C18—N1—C4 | 60.39 (18) |
C7—C8—C9—C10 | 1.2 (3) | C17—C18—N1—C1 | 29.02 (18) |
C8—C9—C10—C11 | −1.2 (3) | C13—C18—N1—C1 | −148.87 (13) |
C9—C10—C11—C12 | −0.1 (3) | C2—C1—N1—C4 | −155.14 (13) |
C10—C11—C12—C7 | 1.4 (3) | C2—C1—N1—C18 | 52.58 (17) |
C8—C7—C12—C11 | −1.5 (2) | C5—C6—N2—C13 | 2.0 (2) |
C6—C7—C12—C11 | 175.58 (15) | C7—C6—N2—C13 | 177.51 (11) |
C18—C13—C14—C15 | 1.4 (2) | C18—C13—N2—C6 | −45.70 (19) |
N2—C13—C14—C15 | 177.09 (14) | C14—C13—N2—C6 | 138.91 (14) |
C13—C14—C15—C16 | −2.2 (2) | C5—C19—N3—C20 | 6.6 (2) |
C14—C15—C16—C17 | 1.0 (2) | C5—C19—N3—C21 | −179.16 (15) |
C15—C16—C17—C18 | 1.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O1i | 0.93 | 2.50 | 3.415 (2) | 170 |
Symmetry code: (i) x+1/2, y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O1i | 0.93 | 2.50 | 3.415 (2) | 170 |
Symmetry code: (i) x+1/2, y+1/2, z. |
References
Boudina, A., Baouid, A., Hasnaoui, A. & Essaber, M. (2006). Synth. Commun. 36, 573–579. Web of Science CrossRef CAS Google Scholar
Bruker (2005). SAINT. Bruker AXS Inc., Madison Wisconsin, USA. Google Scholar
Bruker (2007). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Di 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
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Loughzail, M., Fernandes, J. A., Baouid, A., Essaber, M., Cavaleiro, J. A. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o2075–o2076. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pevarello, P., Amici, R., Colombo, M. & Varasi, M. (1993). J. Chem. Soc. Perkin Trans. 1, pp. 2151–2152. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The benzodiazepine nucleus is extremely important, as it is the base of several drugs and other biologically active compounds with different properties. A large number of structurally modified benzodiazepines have been prepared and evaluated concerning their biological activity (Di Braccio et al., 2001; Pevarello et al., 1993) and may be considered support for the synthesis of more active heterocyclic systems. In this class of compounds, our research team is interested in the synthesis of novel benzodiazepines derived (Loughzail et al., 2011; Boudina et al., 2006). Here we wish to report the synthesis via phase transfer catalysis and the crystallographic studies of the title compound. The title compound was prepared by action of propargyl bromide with 3-dimethylaminomethylene-4-phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one using a catalytic amount of benzyltriethylammonium chloride (TBA-Cl) and sodium hydroxide aqueous solution in benzene. The obtained compound was typically characterized by 1H, 13C NMR, IR and mass spectroscopy, and the stereochemistry (E) of the benzodiazepine was determined by X-ray diffraction. The main geometric feature of the title compound is in good agreement with that observed in a similar compound (Loughzail et al., 2011).