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

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

doi:10.1107/S1600536810005325

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o633

doi:10.1107/S1600536810005325

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

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)

In the title compound, C₂₁H₂₁N₅O₂·H₂O, the seven-membered ring adopts a boat-shaped conformation with the methine C atom as the prow. In the crystal, the water molecule links adjacent molecules by O—H⋯O and O—H⋯N hydrogen bonds into a zigzag chain running along the c axis of the monoclinic cell.

Related literature

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005 ). For the water-free structure of 1-benzyl-4-[(1,5-dimethyl-2,4-dioxobenzo-1,5-diazepin-3-yl)methyl]-1,2,3-triazole, see: Dardouri et al. (2010 ).

Experimental

Crystal data

C₂₁H₂₁N₅O₂·H₂O
M_r = 393.44
Monoclinic, P 2₁ /c
a = 9.6002 (1) Å
b = 11.9497 (2) Å
c = 17.0860 (2) Å
β = 92.527 (1)°
V = 1958.19 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 193 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII diffractometer
34134 measured reflections
4673 independent reflections
3454 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.108
S = 1.02
4673 reflections
272 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O2	0.85 (1)	2.02 (1)	2.836 (2)	161 (2)
O1W—H2⋯N3ⁱ	0.85 (1)	2.10 (1)	2.937 (2)	170 (2)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536810005325/bt5193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005325/bt5193Isup2.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). For the water-free structure of 1-benzyl-4-[(1,5-dimethyl-2,4-dioxobenzo-1,5-diazepin-3-yl)methyl]-1,2,3-triazole, see: Dardouri et al. (2010).

Experimental top

To a solution of 1,5-dimethyl-3-propargyl-1,5-benzodiazepine-2,4-dione (8.26 × 10 ^-4 mol) in toluene (15 ml) was added benzyl azide (9.91 × 10 ^-4 mol). The mixture was stirred under reflux and the reaction was monitored by thin layer chromatography. On completion of the reaction, the solution was concentrated and the residue was purified by column chromatography on silica gel by using a mixture (hexane/ethyl acetate 2/1). Crystals were obtained when the solvent was allowed to evaporate.

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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₂₁H₂₁N₅O₂.H₂O at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.

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

Crystal data top

C₂₁H₂₁N₅O₂·H₂O	F(000) = 832
M_r = 393.44	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7427 reflections
a = 9.6002 (1) Å	θ = 2.1–28.3°
b = 11.9497 (2) Å	µ = 0.09 mm⁻¹
c = 17.0860 (2) Å	T = 193 K
β = 92.527 (1)°	Block, colourless
V = 1958.19 (4) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3454 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 27.5°, θ_min = 2.7°
ϕ and ω scans	h = −12→12
34134 measured reflections	k = −15→15
4673 independent reflections	l = −22→22

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0487P)² + 0.4622P] where P = (F_o² + 2F_c²)/3
4673 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.24 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₁N₅O₂·H₂O	V = 1958.19 (4) Å³
M_r = 393.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6002 (1) Å	µ = 0.09 mm⁻¹
b = 11.9497 (2) Å	T = 193 K
c = 17.0860 (2) Å	0.30 × 0.25 × 0.20 mm
β = 92.527 (1)°

Data collection top

Bruker APEXII diffractometer	3454 reflections with I > 2σ(I)
34134 measured reflections	R_int = 0.040
4673 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	2 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.24 e Å⁻³
4673 reflections	Δρ_min = −0.24 e Å⁻³
272 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.47644 (10)	0.40995 (8)	0.56589 (5)	0.0303 (2)
O2	0.16229 (11)	0.56388 (8)	0.45303 (5)	0.0338 (2)
O1W	0.02018 (13)	0.44707 (13)	0.32908 (8)	0.0618 (4)
H1	0.0749 (19)	0.4689 (17)	0.3660 (9)	0.072 (7)*
H2	0.065 (2)	0.4105 (16)	0.2961 (10)	0.075 (7)*
N1	0.27924 (13)	0.18848 (9)	0.59919 (6)	0.0300 (3)
N2	0.25416 (14)	0.11731 (11)	0.65838 (7)	0.0400 (3)
N3	0.15632 (15)	0.16314 (12)	0.69916 (8)	0.0440 (3)
N4	0.45766 (11)	0.57194 (9)	0.63391 (6)	0.0257 (2)
N5	0.22860 (12)	0.68505 (9)	0.54874 (7)	0.0303 (3)
C1	0.31772 (15)	0.11347 (11)	0.46609 (8)	0.0293 (3)
C2	0.39626 (18)	0.11496 (14)	0.39956 (10)	0.0438 (4)
H2A	0.4877	0.1456	0.4026	0.053*
C3	0.3431 (2)	0.07249 (16)	0.32909 (10)	0.0550 (5)
H3	0.3981	0.0740	0.2842	0.066*
C4	0.2105 (2)	0.02797 (15)	0.32374 (10)	0.0480 (4)
H4	0.1741	−0.0014	0.2754	0.058*
C5	0.13109 (17)	0.02632 (13)	0.38883 (9)	0.0396 (4)
H5	0.0396	−0.0041	0.3853	0.047*
C6	0.18408 (16)	0.06887 (12)	0.45964 (9)	0.0341 (3)
H6	0.1283	0.0675	0.5042	0.041*
C7	0.38193 (15)	0.15738 (12)	0.54260 (9)	0.0343 (3)
H7A	0.4442	0.0993	0.5661	0.041*
H7B	0.4398	0.2236	0.5316	0.041*
C8	0.19589 (14)	0.28012 (11)	0.60124 (8)	0.0270 (3)
C9	0.11891 (17)	0.26208 (14)	0.66575 (9)	0.0376 (3)
H9	0.0500	0.3114	0.6842	0.045*
C10	0.19235 (14)	0.37276 (11)	0.54245 (7)	0.0262 (3)
H10A	0.0954	0.3825	0.5214	0.031*
H10B	0.2503	0.3515	0.4983	0.031*
C11	0.40317 (13)	0.48442 (10)	0.59142 (7)	0.0237 (3)
C12	0.24519 (13)	0.48458 (11)	0.57649 (7)	0.0238 (3)
H12	0.1999	0.4983	0.6272	0.029*
C13	0.20750 (13)	0.58015 (11)	0.52044 (8)	0.0260 (3)
C14	0.26507 (14)	0.70923 (11)	0.62872 (8)	0.0285 (3)
C15	0.19149 (16)	0.79278 (12)	0.66644 (10)	0.0406 (4)
H15	0.1132	0.8267	0.6401	0.049*
C16	0.23055 (17)	0.82671 (13)	0.74123 (10)	0.0458 (4)
H16	0.1806	0.8847	0.7657	0.055*
C17	0.34254 (18)	0.77633 (14)	0.78060 (9)	0.0429 (4)
H17	0.3707	0.8005	0.8319	0.052*
C18	0.41355 (16)	0.69081 (12)	0.74538 (8)	0.0342 (3)
H18	0.4889	0.6551	0.7733	0.041*
C19	0.37605 (14)	0.65595 (11)	0.66908 (7)	0.0262 (3)
C20	0.60870 (14)	0.57233 (12)	0.65173 (9)	0.0326 (3)
H20A	0.6558	0.5310	0.6110	0.049*
H20B	0.6285	0.5366	0.7026	0.049*
H20C	0.6427	0.6497	0.6535	0.049*
C21	0.19423 (18)	0.77880 (13)	0.49550 (10)	0.0433 (4)
H21A	0.2198	0.7593	0.4423	0.065*
H21B	0.2461	0.8455	0.5131	0.065*
H21C	0.0939	0.7940	0.4957	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0280 (5)	0.0271 (5)	0.0357 (5)	0.0058 (4)	0.0003 (4)	−0.0025 (4)
O2	0.0347 (6)	0.0368 (6)	0.0290 (5)	0.0067 (4)	−0.0072 (4)	−0.0011 (4)
O1W	0.0327 (7)	0.0899 (11)	0.0629 (8)	−0.0016 (7)	0.0039 (6)	−0.0415 (8)
N1	0.0340 (7)	0.0267 (6)	0.0289 (6)	0.0004 (5)	−0.0036 (5)	0.0020 (5)
N2	0.0487 (8)	0.0347 (7)	0.0357 (6)	−0.0049 (6)	−0.0073 (6)	0.0083 (6)
N3	0.0497 (9)	0.0464 (8)	0.0356 (7)	−0.0104 (7)	−0.0001 (6)	0.0081 (6)
N4	0.0225 (6)	0.0286 (6)	0.0257 (5)	0.0015 (4)	−0.0009 (4)	−0.0022 (5)
N5	0.0319 (6)	0.0249 (6)	0.0336 (6)	0.0048 (5)	−0.0035 (5)	0.0013 (5)
C1	0.0335 (8)	0.0185 (6)	0.0359 (7)	0.0047 (5)	0.0022 (6)	0.0012 (5)
C2	0.0440 (10)	0.0384 (9)	0.0498 (9)	−0.0047 (7)	0.0128 (7)	−0.0010 (7)
C3	0.0680 (13)	0.0574 (11)	0.0410 (9)	−0.0038 (9)	0.0197 (9)	−0.0051 (8)
C4	0.0634 (12)	0.0453 (10)	0.0348 (8)	0.0042 (8)	−0.0030 (8)	−0.0043 (7)
C5	0.0391 (9)	0.0356 (8)	0.0434 (8)	0.0008 (7)	−0.0051 (7)	−0.0024 (7)
C6	0.0359 (8)	0.0315 (7)	0.0352 (7)	0.0013 (6)	0.0034 (6)	0.0009 (6)
C7	0.0305 (8)	0.0281 (7)	0.0440 (8)	0.0059 (6)	−0.0021 (6)	−0.0030 (6)
C8	0.0267 (7)	0.0259 (7)	0.0281 (6)	−0.0022 (5)	−0.0019 (5)	−0.0035 (5)
C9	0.0380 (8)	0.0407 (8)	0.0343 (7)	−0.0040 (7)	0.0036 (6)	0.0006 (7)
C10	0.0256 (7)	0.0259 (6)	0.0267 (6)	0.0005 (5)	−0.0019 (5)	−0.0018 (5)
C11	0.0265 (7)	0.0238 (6)	0.0206 (6)	0.0020 (5)	−0.0001 (5)	0.0026 (5)
C12	0.0230 (6)	0.0252 (6)	0.0233 (6)	0.0024 (5)	0.0005 (5)	−0.0012 (5)
C13	0.0209 (6)	0.0279 (7)	0.0291 (6)	0.0043 (5)	0.0001 (5)	−0.0008 (5)
C14	0.0276 (7)	0.0232 (6)	0.0350 (7)	−0.0022 (5)	0.0027 (5)	−0.0035 (5)
C15	0.0317 (8)	0.0308 (8)	0.0592 (10)	0.0033 (6)	0.0016 (7)	−0.0127 (7)
C16	0.0397 (9)	0.0375 (9)	0.0612 (10)	−0.0042 (7)	0.0145 (8)	−0.0241 (8)
C17	0.0465 (10)	0.0447 (9)	0.0382 (8)	−0.0120 (8)	0.0092 (7)	−0.0174 (7)
C18	0.0367 (8)	0.0355 (8)	0.0303 (7)	−0.0053 (6)	0.0009 (6)	−0.0045 (6)
C19	0.0262 (7)	0.0250 (6)	0.0278 (6)	−0.0028 (5)	0.0049 (5)	−0.0032 (5)
C20	0.0246 (7)	0.0345 (8)	0.0384 (7)	0.0003 (6)	−0.0031 (6)	−0.0033 (6)
C21	0.0497 (10)	0.0293 (8)	0.0497 (9)	0.0043 (7)	−0.0098 (7)	0.0087 (7)

Geometric parameters (Å, º) top

O1—C11	1.2263 (15)	C7—H7A	0.9900
O2—C13	1.2283 (15)	C7—H7B	0.9900
O1W—H1	0.85 (1)	C8—C9	1.371 (2)
O1W—H2	0.85 (1)	C8—C10	1.4942 (18)
N1—N2	1.3511 (16)	C9—H9	0.9500
N1—C8	1.3576 (17)	C10—C12	1.5346 (18)
N1—C7	1.4591 (19)	C10—H10A	0.9900
N2—N3	1.314 (2)	C10—H10B	0.9900
N3—C9	1.354 (2)	C11—C12	1.5269 (18)
N4—C11	1.3642 (16)	C12—C13	1.5237 (18)
N4—C19	1.4227 (17)	C12—H12	1.0000
N4—C20	1.4685 (17)	C14—C15	1.3968 (19)
N5—C13	1.3556 (17)	C14—C19	1.3970 (19)
N5—C14	1.4252 (17)	C15—C16	1.377 (2)
N5—C21	1.4714 (18)	C15—H15	0.9500
C1—C6	1.389 (2)	C16—C17	1.381 (3)
C1—C2	1.392 (2)	C16—H16	0.9500
C1—C7	1.5142 (19)	C17—C18	1.381 (2)
C2—C3	1.383 (2)	C17—H17	0.9500
C2—H2A	0.9500	C18—C19	1.4006 (18)
C3—C4	1.379 (3)	C18—H18	0.9500
C3—H3	0.9500	C20—H20A	0.9800
C4—C5	1.376 (2)	C20—H20B	0.9800
C4—H4	0.9500	C20—H20C	0.9800
C5—C6	1.388 (2)	C21—H21A	0.9800
C5—H5	0.9500	C21—H21B	0.9800
C6—H6	0.9500	C21—H21C	0.9800

H1—O1W—H2	110 (2)	C8—C10—H10B	109.0
N2—N1—C8	111.33 (12)	C12—C10—H10B	109.0
N2—N1—C7	118.92 (12)	H10A—C10—H10B	107.8
C8—N1—C7	129.70 (12)	O1—C11—N4	122.22 (12)
N3—N2—N1	106.85 (12)	O1—C11—C12	121.50 (11)
N2—N3—C9	108.83 (12)	N4—C11—C12	116.28 (11)
C11—N4—C19	124.08 (11)	C13—C12—C11	108.21 (10)
C11—N4—C20	117.69 (11)	C13—C12—C10	110.43 (10)
C19—N4—C20	117.86 (11)	C11—C12—C10	111.81 (10)
C13—N5—C14	123.78 (11)	C13—C12—H12	108.8
C13—N5—C21	117.24 (11)	C11—C12—H12	108.8
C14—N5—C21	118.51 (11)	C10—C12—H12	108.8
C6—C1—C2	118.15 (14)	O2—C13—N5	121.46 (12)
C6—C1—C7	122.74 (13)	O2—C13—C12	122.34 (12)
C2—C1—C7	119.09 (13)	N5—C13—C12	116.19 (11)
C3—C2—C1	120.93 (16)	C15—C14—C19	119.22 (13)
C3—C2—H2A	119.5	C15—C14—N5	118.65 (13)
C1—C2—H2A	119.5	C19—C14—N5	122.05 (12)
C4—C3—C2	120.21 (16)	C16—C15—C14	121.08 (15)
C4—C3—H3	119.9	C16—C15—H15	119.5
C2—C3—H3	119.9	C14—C15—H15	119.5
C5—C4—C3	119.64 (16)	C15—C16—C17	119.87 (14)
C5—C4—H4	120.2	C15—C16—H16	120.1
C3—C4—H4	120.2	C17—C16—H16	120.1
C4—C5—C6	120.30 (16)	C16—C17—C18	119.93 (14)
C4—C5—H5	119.8	C16—C17—H17	120.0
C6—C5—H5	119.8	C18—C17—H17	120.0
C5—C6—C1	120.76 (14)	C17—C18—C19	120.94 (14)
C5—C6—H6	119.6	C17—C18—H18	119.5
C1—C6—H6	119.6	C19—C18—H18	119.5
N1—C7—C1	113.52 (12)	C14—C19—C18	118.89 (13)
N1—C7—H7A	108.9	C14—C19—N4	122.37 (11)
C1—C7—H7A	108.9	C18—C19—N4	118.64 (12)
N1—C7—H7B	108.9	N4—C20—H20A	109.5
C1—C7—H7B	108.9	N4—C20—H20B	109.5
H7A—C7—H7B	107.7	H20A—C20—H20B	109.5
N1—C8—C9	103.48 (12)	N4—C20—H20C	109.5
N1—C8—C10	125.18 (12)	H20A—C20—H20C	109.5
C9—C8—C10	131.30 (13)	H20B—C20—H20C	109.5
N3—C9—C8	109.50 (14)	N5—C21—H21A	109.5
N3—C9—H9	125.2	N5—C21—H21B	109.5
C8—C9—H9	125.2	H21A—C21—H21B	109.5
C8—C10—C12	113.14 (10)	N5—C21—H21C	109.5
C8—C10—H10A	109.0	H21A—C21—H21C	109.5
C12—C10—H10A	109.0	H21B—C21—H21C	109.5

C8—N1—N2—N3	−0.75 (15)	N4—C11—C12—C10	−169.06 (10)
C7—N1—N2—N3	−178.41 (12)	C8—C10—C12—C13	−166.63 (11)
N1—N2—N3—C9	0.48 (16)	C8—C10—C12—C11	72.82 (14)
C6—C1—C2—C3	−0.4 (2)	C14—N5—C13—O2	172.36 (12)
C7—C1—C2—C3	178.00 (15)	C21—N5—C13—O2	0.4 (2)
C1—C2—C3—C4	0.1 (3)	C14—N5—C13—C12	−8.58 (19)
C2—C3—C4—C5	0.2 (3)	C21—N5—C13—C12	179.44 (12)
C3—C4—C5—C6	−0.2 (3)	C11—C12—C13—O2	111.69 (14)
C4—C5—C6—C1	−0.1 (2)	C10—C12—C13—O2	−10.99 (18)
C2—C1—C6—C5	0.5 (2)	C11—C12—C13—N5	−67.36 (14)
C7—C1—C6—C5	−177.93 (13)	C10—C12—C13—N5	169.96 (11)
N2—N1—C7—C1	101.20 (14)	C13—N5—C14—C15	−132.02 (15)
C8—N1—C7—C1	−75.96 (18)	C21—N5—C14—C15	39.86 (19)
C6—C1—C7—N1	−22.18 (19)	C13—N5—C14—C19	51.2 (2)
C2—C1—C7—N1	159.45 (13)	C21—N5—C14—C19	−136.95 (14)
N2—N1—C8—C9	0.69 (15)	C19—C14—C15—C16	2.9 (2)
C7—N1—C8—C9	178.03 (13)	N5—C14—C15—C16	−173.96 (14)
N2—N1—C8—C10	−177.24 (12)	C14—C15—C16—C17	−1.2 (3)
C7—N1—C8—C10	0.1 (2)	C15—C16—C17—C18	−1.1 (2)
N2—N3—C9—C8	−0.06 (17)	C16—C17—C18—C19	1.7 (2)
N1—C8—C9—N3	−0.38 (16)	C15—C14—C19—C18	−2.3 (2)
C10—C8—C9—N3	177.37 (13)	N5—C14—C19—C18	174.49 (12)
N1—C8—C10—C12	−113.56 (14)	C15—C14—C19—N4	−178.56 (13)
C9—C8—C10—C12	69.12 (19)	N5—C14—C19—N4	−1.8 (2)
C19—N4—C11—O1	−175.58 (12)	C17—C18—C19—C14	0.0 (2)
C20—N4—C11—O1	−2.71 (18)	C17—C18—C19—N4	176.42 (13)
C19—N4—C11—C12	5.01 (17)	C11—N4—C19—C14	−46.74 (18)
C20—N4—C11—C12	177.88 (11)	C20—N4—C19—C14	140.41 (13)
O1—C11—C12—C13	−110.30 (13)	C11—N4—C19—C18	137.00 (13)
N4—C11—C12—C13	69.11 (14)	C20—N4—C19—C18	−35.85 (17)
O1—C11—C12—C10	11.53 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O2	0.85 (1)	2.02 (1)	2.836 (2)	161 (2)
O1W—H2···N3ⁱ	0.85 (1)	2.10 (1)	2.937 (2)	170 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₅O₂·H₂O
M_r	393.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	9.6002 (1), 11.9497 (2), 17.0860 (2)
β (°)	92.527 (1)
V (Å³)	1958.19 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	34134, 4673, 3454
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.108, 1.02
No. of reflections	4673
No. of parameters	272
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.24

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O2	0.85 (1)	2.02 (1)	2.836 (2)	161 (2)
O1W—H2···N3ⁱ	0.85 (1)	2.10 (1)	2.937 (2)	170 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

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
Dardouri, R., Kandri Rodi, Y., Saffon, N., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o632. Web of Science CSD CrossRef IUCr Journals 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 o633

doi:10.1107/S1600536810005325

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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-5-yl)methyl]-1,5-di­methyl-1,5-benzodiazepine-2,4-dione monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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