3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione

Dardouri, R.; Kandri Rodi, Y.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810005313

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o632

doi:10.1107/S1600536810005313

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3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione

R. Dardouri,^a Y. Kandri Rodi,^a Natalie Saffon,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, ^bService Commun Rayons-X FR2599, Université Paul Sabatier Bâtiment 2R1, 118 Route de Narbonne, Toulouse, France, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 February 2010; accepted 9 February 2010; online 13 February 2010)

The title compound, C₂₁H₂₁N₅O₂, is a 1,4-dimethyl-1,2,3-triazole having dimethylbenzodiazepindione and phenyl substituents on each methyl group; the substituents are positioned on opposite sides of the five-membered ring. The seven-membered fused-ring of the larger substituent adopts a boat-shaped conformation (with the methine C atom as the prow).

Related literature

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005 ).

Experimental

Crystal data

C₂₁H₂₁N₅O₂
M_r = 375.43
Triclinic, $[P \overline 1]$
a = 8.3380 (3) Å
b = 9.1033 (3) Å
c = 13.4796 (4) Å
α = 95.385 (2)°
β = 107.840 (2)°
γ = 101.768 (2)°
V = 939.97 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.28 × 0.18 × 0.08 mm

Data collection

Bruker APEXII diffractometer
7973 measured reflections
3279 independent reflections
2132 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.141
S = 1.05
3279 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005313/bt5192sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005313/bt5192Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005).

Experimental top

To a solution of 1,5-dimethyl-3-propargyl-1,5-benzodiazepine-2,4-dione (1 mmol) in t-butyl alcohol/water (1/2, 8 ml) was added copper sulfate pentahydrate (1 mmol), sodium ascorbate (2 mmol) and benzyl azide (5 mmol). The mixture was stirred for 8 h. The solution was then diluted with water (20 ml) and the organic compound extracted with ethyl acetate (2 × 20 ml). The extracts were washed with brine and dried over sodium sulfate. The compound was recrystallized from ether to give colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: 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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₁H₂₁N₅O₂ at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.

3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl- 1,5-benzodiazepine-2,4-dione top

Crystal data top

C₂₁H₂₁N₅O₂	Z = 2
M_r = 375.43	F(000) = 396
Triclinic, P1	D_x = 1.326 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3380 (3) Å	Cell parameters from 1894 reflections
b = 9.1033 (3) Å	θ = 2.3–26.8°
c = 13.4796 (4) Å	µ = 0.09 mm⁻¹
α = 95.385 (2)°	T = 293 K
β = 107.840 (2)°	Block, colourless
γ = 101.768 (2)°	0.28 × 0.18 × 0.08 mm
V = 939.97 (5) Å³

Data collection top

Bruker APEXII diffractometer	2132 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 25.0°, θ_min = 1.6°
ϕ and ω scans	h = −8→9
7973 measured reflections	k = −10→10
3279 independent reflections	l = −16→15

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.076P)²] where P = (F_o² + 2F_c²)/3
3279 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₂₁N₅O₂	γ = 101.768 (2)°
M_r = 375.43	V = 939.97 (5) Å³
Triclinic, P1	Z = 2
a = 8.3380 (3) Å	Mo Kα radiation
b = 9.1033 (3) Å	µ = 0.09 mm⁻¹
c = 13.4796 (4) Å	T = 293 K
α = 95.385 (2)°	0.28 × 0.18 × 0.08 mm
β = 107.840 (2)°

Data collection top

Bruker APEXII diffractometer	2132 reflections with I > 2σ(I)
7973 measured reflections	R_int = 0.037
3279 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
3279 reflections	Δρ_min = −0.22 e Å⁻³
255 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.50707 (19)	0.14271 (17)	0.38773 (13)	0.0383 (4)
O2	0.8254 (2)	0.2153 (2)	0.23619 (15)	0.0501 (5)
N1	0.8448 (2)	0.2106 (2)	0.71289 (16)	0.0366 (5)
N2	0.9062 (2)	0.3607 (2)	0.71872 (16)	0.0376 (5)
N3	0.9231 (2)	0.3802 (2)	0.62613 (16)	0.0359 (5)
N4	0.4763 (2)	0.37357 (19)	0.34845 (14)	0.0283 (4)
N5	0.6925 (2)	0.4101 (2)	0.21476 (15)	0.0310 (5)
C1	0.9776 (3)	0.1642 (3)	0.89419 (19)	0.0359 (6)
C2	1.0765 (3)	0.0598 (3)	0.8911 (2)	0.0409 (6)
H2	1.0396	−0.0190	0.8339	0.049*
C3	1.2289 (4)	0.0720 (4)	0.9720 (3)	0.0650 (9)
H3	1.2943	0.0013	0.9694	0.078*
C4	1.2843 (5)	0.1865 (6)	1.0557 (3)	0.0935 (15)
H4	1.3868	0.1928	1.1106	0.112*
C5	1.1909 (6)	0.2932 (5)	1.0604 (3)	0.0947 (16)
H5	1.2312	0.3731	1.1171	0.114*
C6	1.0353 (5)	0.2807 (3)	0.9796 (2)	0.0610 (9)
H6	0.9699	0.3512	0.9831	0.073*
C7	0.8123 (3)	0.1525 (3)	0.8049 (2)	0.0442 (7)
H7A	0.7476	0.0468	0.7836	0.053*
H7B	0.7415	0.2096	0.8294	0.053*
C8	0.8216 (3)	0.1340 (3)	0.6177 (2)	0.0364 (6)
H8	0.7799	0.0296	0.5944	0.044*
C9	0.8726 (3)	0.2424 (3)	0.56202 (19)	0.0321 (6)
C10	0.8729 (3)	0.2271 (3)	0.45103 (19)	0.0346 (6)
H10A	0.8279	0.1209	0.4181	0.042*
H10B	0.9915	0.2590	0.4515	0.042*
C11	0.5716 (3)	0.2698 (2)	0.37552 (18)	0.0282 (5)
C12	0.7630 (3)	0.3225 (2)	0.38576 (18)	0.0284 (5)
H12	0.8070	0.4292	0.4202	0.034*
C13	0.7673 (3)	0.3110 (3)	0.27368 (19)	0.0324 (6)
C14	0.6468 (3)	0.5362 (2)	0.26045 (17)	0.0286 (5)
C15	0.6992 (3)	0.6803 (3)	0.2368 (2)	0.0357 (6)
H15	0.7607	0.6919	0.1898	0.043*
C16	0.6620 (3)	0.8055 (3)	0.2814 (2)	0.0403 (6)
H16	0.6977	0.9004	0.2641	0.048*
C17	0.5715 (3)	0.7908 (3)	0.3521 (2)	0.0385 (6)
H17	0.5500	0.8760	0.3844	0.046*
C18	0.5137 (3)	0.6485 (2)	0.37394 (19)	0.0324 (5)
H18	0.4513	0.6384	0.4205	0.039*
C19	0.5468 (3)	0.5196 (2)	0.32765 (17)	0.0268 (5)
C20	0.2922 (3)	0.3329 (3)	0.3420 (2)	0.0364 (6)
H20A	0.2357	0.2351	0.2985	0.055*
H20B	0.2356	0.4080	0.3118	0.055*
H20C	0.2857	0.3293	0.4117	0.055*
C21	0.7053 (3)	0.4078 (3)	0.1087 (2)	0.0440 (7)
H21A	0.8197	0.4626	0.1138	0.066*
H21B	0.6207	0.4549	0.0672	0.066*
H21C	0.6841	0.3044	0.0756	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0331 (9)	0.0258 (9)	0.0594 (12)	0.0034 (7)	0.0207 (8)	0.0141 (8)
O2	0.0635 (12)	0.0451 (11)	0.0596 (12)	0.0259 (9)	0.0373 (10)	0.0104 (9)
N1	0.0281 (10)	0.0379 (12)	0.0463 (13)	0.0062 (9)	0.0139 (9)	0.0187 (10)
N2	0.0316 (11)	0.0349 (12)	0.0476 (13)	0.0078 (9)	0.0133 (10)	0.0139 (9)
N3	0.0278 (10)	0.0370 (12)	0.0461 (13)	0.0085 (9)	0.0138 (9)	0.0160 (10)
N4	0.0219 (9)	0.0264 (10)	0.0388 (12)	0.0037 (8)	0.0138 (8)	0.0080 (8)
N5	0.0315 (10)	0.0314 (11)	0.0333 (11)	0.0061 (8)	0.0163 (9)	0.0067 (9)
C1	0.0399 (13)	0.0350 (14)	0.0344 (14)	−0.0005 (11)	0.0197 (11)	0.0095 (11)
C2	0.0387 (14)	0.0420 (15)	0.0435 (16)	0.0041 (11)	0.0176 (12)	0.0138 (12)
C3	0.0380 (16)	0.089 (2)	0.070 (2)	0.0062 (16)	0.0172 (16)	0.048 (2)
C4	0.061 (2)	0.113 (3)	0.060 (3)	−0.043 (2)	−0.0130 (18)	0.048 (3)
C5	0.138 (4)	0.069 (3)	0.0316 (19)	−0.049 (3)	0.014 (2)	0.0020 (17)
C6	0.099 (2)	0.0374 (16)	0.0501 (19)	−0.0039 (15)	0.0430 (19)	0.0055 (13)
C7	0.0399 (14)	0.0494 (16)	0.0526 (17)	0.0084 (12)	0.0261 (13)	0.0233 (13)
C8	0.0334 (13)	0.0277 (13)	0.0478 (16)	0.0042 (10)	0.0139 (12)	0.0108 (11)
C9	0.0200 (11)	0.0302 (13)	0.0494 (15)	0.0079 (9)	0.0128 (10)	0.0147 (11)
C10	0.0288 (12)	0.0313 (13)	0.0501 (16)	0.0102 (10)	0.0185 (11)	0.0132 (11)
C11	0.0291 (12)	0.0243 (12)	0.0338 (13)	0.0043 (9)	0.0153 (10)	0.0067 (9)
C12	0.0272 (11)	0.0234 (11)	0.0385 (14)	0.0054 (9)	0.0162 (10)	0.0074 (10)
C13	0.0292 (12)	0.0279 (13)	0.0432 (15)	0.0034 (10)	0.0190 (11)	0.0055 (11)
C14	0.0223 (11)	0.0300 (12)	0.0331 (13)	0.0059 (9)	0.0084 (10)	0.0081 (10)
C15	0.0267 (12)	0.0379 (14)	0.0472 (15)	0.0062 (10)	0.0170 (11)	0.0185 (12)
C16	0.0310 (13)	0.0294 (13)	0.0630 (18)	0.0065 (10)	0.0165 (12)	0.0194 (12)
C17	0.0321 (13)	0.0273 (13)	0.0577 (17)	0.0101 (10)	0.0153 (12)	0.0076 (11)
C18	0.0254 (11)	0.0316 (13)	0.0411 (14)	0.0088 (10)	0.0109 (10)	0.0068 (10)
C19	0.0229 (11)	0.0244 (12)	0.0322 (13)	0.0053 (9)	0.0078 (9)	0.0070 (9)
C20	0.0234 (12)	0.0421 (14)	0.0460 (15)	0.0032 (10)	0.0164 (11)	0.0116 (11)
C21	0.0493 (15)	0.0498 (16)	0.0386 (15)	0.0088 (12)	0.0242 (13)	0.0103 (12)

Geometric parameters (Å, º) top

O1—C11	1.221 (2)	C7—H7B	0.9700
O2—C13	1.221 (3)	C8—C9	1.372 (3)
N1—C8	1.340 (3)	C8—H8	0.9300
N1—N2	1.344 (3)	C9—C10	1.490 (3)
N1—C7	1.470 (3)	C10—C12	1.531 (3)
N2—N3	1.322 (3)	C10—H10A	0.9700
N3—C9	1.362 (3)	C10—H10B	0.9700
N4—C11	1.361 (3)	C11—C12	1.528 (3)
N4—C19	1.429 (3)	C12—C13	1.517 (3)
N4—C20	1.477 (3)	C12—H12	0.9800
N5—C13	1.376 (3)	C14—C15	1.394 (3)
N5—C14	1.425 (3)	C14—C19	1.406 (3)
N5—C21	1.464 (3)	C15—C16	1.374 (3)
C1—C6	1.380 (4)	C15—H15	0.9300
C1—C2	1.385 (3)	C16—C17	1.385 (3)
C1—C7	1.503 (4)	C16—H16	0.9300
C2—C3	1.374 (4)	C17—C18	1.379 (3)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.355 (6)	C18—C19	1.394 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.371 (6)	C20—H20A	0.9600
C4—H4	0.9300	C20—H20B	0.9600
C5—C6	1.390 (5)	C20—H20C	0.9600
C5—H5	0.9300	C21—H21A	0.9600
C6—H6	0.9300	C21—H21B	0.9600
C7—H7A	0.9700	C21—H21C	0.9600

C8—N1—N2	111.21 (19)	C12—C10—H10B	109.2
C8—N1—C7	129.2 (2)	H10A—C10—H10B	107.9
N2—N1—C7	119.6 (2)	O1—C11—N4	122.12 (19)
N3—N2—N1	106.65 (19)	O1—C11—C12	122.85 (19)
N2—N3—C9	109.22 (18)	N4—C11—C12	115.00 (18)
C11—N4—C19	123.05 (17)	C13—C12—C11	105.92 (18)
C11—N4—C20	117.89 (17)	C13—C12—C10	112.28 (18)
C19—N4—C20	119.06 (17)	C11—C12—C10	111.64 (17)
C13—N5—C14	122.66 (19)	C13—C12—H12	109.0
C13—N5—C21	116.48 (19)	C11—C12—H12	109.0
C14—N5—C21	118.77 (18)	C10—C12—H12	109.0
C6—C1—C2	118.8 (3)	O2—C13—N5	121.9 (2)
C6—C1—C7	120.7 (3)	O2—C13—C12	122.3 (2)
C2—C1—C7	120.4 (2)	N5—C13—C12	115.6 (2)
C3—C2—C1	120.4 (3)	C15—C14—C19	118.5 (2)
C3—C2—H2	119.8	C15—C14—N5	119.6 (2)
C1—C2—H2	119.8	C19—C14—N5	121.94 (19)
C4—C3—C2	120.4 (3)	C16—C15—C14	121.4 (2)
C4—C3—H3	119.8	C16—C15—H15	119.3
C2—C3—H3	119.8	C14—C15—H15	119.3
C3—C4—C5	120.7 (3)	C15—C16—C17	120.2 (2)
C3—C4—H4	119.7	C15—C16—H16	119.9
C5—C4—H4	119.7	C17—C16—H16	119.9
C4—C5—C6	119.4 (3)	C18—C17—C16	119.3 (2)
C4—C5—H5	120.3	C18—C17—H17	120.4
C6—C5—H5	120.3	C16—C17—H17	120.4
C1—C6—C5	120.3 (3)	C17—C18—C19	121.4 (2)
C1—C6—H6	119.9	C17—C18—H18	119.3
C5—C6—H6	119.9	C19—C18—H18	119.3
N1—C7—C1	112.38 (19)	C18—C19—C14	119.15 (19)
N1—C7—H7A	109.1	C18—C19—N4	119.24 (19)
C1—C7—H7A	109.1	C14—C19—N4	121.60 (19)
N1—C7—H7B	109.1	N4—C20—H20A	109.5
C1—C7—H7B	109.1	N4—C20—H20B	109.5
H7A—C7—H7B	107.9	H20A—C20—H20B	109.5
N1—C8—C9	105.3 (2)	N4—C20—H20C	109.5
N1—C8—H8	127.4	H20A—C20—H20C	109.5
C9—C8—H8	127.4	H20B—C20—H20C	109.5
N3—C9—C8	107.7 (2)	N5—C21—H21A	109.5
N3—C9—C10	122.0 (2)	N5—C21—H21B	109.5
C8—C9—C10	130.3 (2)	H21A—C21—H21B	109.5
C9—C10—C12	112.07 (18)	N5—C21—H21C	109.5
C9—C10—H10A	109.2	H21A—C21—H21C	109.5
C12—C10—H10A	109.2	H21B—C21—H21C	109.5
C9—C10—H10B	109.2

C8—N1—N2—N3	−0.3 (2)	N4—C11—C12—C10	160.55 (19)
C7—N1—N2—N3	179.89 (18)	C9—C10—C12—C13	178.25 (18)
N1—N2—N3—C9	0.0 (2)	C9—C10—C12—C11	−63.0 (2)
C6—C1—C2—C3	0.4 (3)	C14—N5—C13—O2	−170.7 (2)
C7—C1—C2—C3	179.0 (2)	C21—N5—C13—O2	−7.4 (3)
C1—C2—C3—C4	−0.2 (4)	C14—N5—C13—C12	12.8 (3)
C2—C3—C4—C5	−0.9 (5)	C21—N5—C13—C12	176.14 (18)
C3—C4—C5—C6	1.8 (5)	C11—C12—C13—O2	−109.6 (2)
C2—C1—C6—C5	0.5 (4)	C10—C12—C13—O2	12.5 (3)
C7—C1—C6—C5	−178.1 (2)	C11—C12—C13—N5	66.9 (2)
C4—C5—C6—C1	−1.6 (5)	C10—C12—C13—N5	−171.04 (18)
C8—N1—C7—C1	110.1 (3)	C13—N5—C14—C15	130.3 (2)
N2—N1—C7—C1	−70.1 (3)	C21—N5—C14—C15	−32.6 (3)
C6—C1—C7—N1	100.6 (3)	C13—N5—C14—C19	−50.9 (3)
C2—C1—C7—N1	−78.0 (3)	C21—N5—C14—C19	146.1 (2)
N2—N1—C8—C9	0.5 (2)	C19—C14—C15—C16	3.0 (3)
C7—N1—C8—C9	−179.7 (2)	N5—C14—C15—C16	−178.2 (2)
N2—N3—C9—C8	0.3 (2)	C14—C15—C16—C17	0.4 (4)
N2—N3—C9—C10	178.56 (19)	C15—C16—C17—C18	−2.4 (4)
N1—C8—C9—N3	−0.5 (2)	C16—C17—C18—C19	1.0 (3)
N1—C8—C9—C10	−178.5 (2)	C17—C18—C19—C14	2.4 (3)
N3—C9—C10—C12	−56.4 (3)	C17—C18—C19—N4	−176.7 (2)
C8—C9—C10—C12	121.4 (2)	C15—C14—C19—C18	−4.3 (3)
C19—N4—C11—O1	−176.2 (2)	N5—C14—C19—C18	176.90 (19)
C20—N4—C11—O1	4.7 (3)	C15—C14—C19—N4	174.74 (18)
C19—N4—C11—C12	1.9 (3)	N5—C14—C19—N4	−4.0 (3)
C20—N4—C11—C12	−177.20 (19)	C11—N4—C19—C18	−132.9 (2)
O1—C11—C12—C13	101.1 (2)	C20—N4—C19—C18	46.1 (3)
N4—C11—C12—C13	−76.9 (2)	C11—N4—C19—C14	48.0 (3)
O1—C11—C12—C10	−21.4 (3)	C20—N4—C19—C14	−132.9 (2)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₅O₂
M_r	375.43
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.3380 (3), 9.1033 (3), 13.4796 (4)
α, β, γ (°)	95.385 (2), 107.840 (2), 101.768 (2)
V (Å³)	939.97 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.18 × 0.08

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7973, 3279, 2132
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.141, 1.05
No. of reflections	3279
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

The authors thank the Université Sidi Mohamed Ben Abdallah, the Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mondieig, M., Négrier, Ph., Léger, J. M., Benali, B., Lazar, Z., Elassyry, A., Jarmouni, C., Lakhrissi, B. & Massoui, M. (2005). Anal. Sci. X-Ray Struct. Anal. Online, 21, x145–x146. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

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Volume 66| Part 3| March 2010| Page o632

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

3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-di­methyl-1,5-benzodiazepine-2,4-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione