4-Benzyl-6-bromo-2-(4-methoxy­phen­yl)-4H-imidazo[4,5-b]pyridine monohydrate

Ouzidan, Y.; Kandri Rodi, Y.; Obbade, S.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810010391

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o947

doi:10.1107/S1600536810010391

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4-Benzyl-6-bromo-2-(4-methoxyphenyl)-4H-imidazo[4,5-b]pyridine monohydrate

Y. Ouzidan,^a Y. Kandri Rodi,^b S. Obbade,^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, ^bLaboratoire d'Electrochimie et de Physicochimie des Matériaux et des Interfaces, A313 Domaine Universitaire, 38402 St Martin d'Hères, Grenoble, 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 11 March 2010; accepted 19 March 2010; online 27 March 2010)

The imidazopyridine fused ring in the title compound, C₂₀H₁₆BrN₃O·H₂O, is coplanar with the aromatic ring at the 2-position [dihedral angle = 5.2 (1)°]. In the five-membered imidazo portion, the C—N bond whose C atom is also connected to the pyridine N atom has predominantly double-bond character [1.334 (2) Å] whereas the C—N bond whose atom is connected to the pyridine C atom has predominantly single-bond character [1.371 (2) Å]. The water molecule engages in hydrogen bonding with the latter N atom; it is also connected to a symmetry-related water molecule, generating a linear chain structure.

Related literature

For the crystal structure of 4-benzyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine, see: Ouzidan et al. (2010 ).

Experimental

Crystal data

C₂₀H₁₆BrN₃O·H₂O
M_r = 412.28
Monoclinic, P 2₁ /c
a = 10.5924 (2) Å
b = 5.4544 (1) Å
c = 31.7444 (7) Å
β = 100.292 (1)°
V = 1804.53 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 293 K
0.29 × 0.13 × 0.09 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.556, T_max = 0.820
25327 measured reflections
5183 independent reflections
3751 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.098
S = 1.02
5183 reflections
244 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯N2	0.85 (1)	2.30 (2)	3.092 (3)	155 (5)
O1w—H12⋯O1Wⁱ	0.85 (1)	2.30 (2)	3.119 (2)	162 (5)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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/S1600536810010391/pk2233sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010391/pk2233Isup2.hkl

checkCIF report

Comment top

Imidazo[4,5-b]pyridines are a class of sedative drugs. In the previous study, we reacted 6-bromo-2-phenyl-1H-imidazo[4,5-b]pyridine with benzyl chloride in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to form 4-benzyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine (Ouzidan et al., 2010). The study is extended to the synthesis of the 2(4-methoxyphenyl) analog to furnish the title hydrate (Scheme I, Fig. 1). The imidazopyridine fused-ring in the C₂₀H₁₆BrN₃O molecule is co-planar with the aromatic ring at the 2-position [dihedral angle 5.2 (1) °]. In the five-membered imidazo portion, the carbon–nitrogen bond whose carbon atom is also connected to the pyridine nitrogen atom is a double bond [1.334 (2) Å] whereas the carbon–nitrogen bond whose atom is connected to the pyridine carbon atom is a single bond [1.371 (2) Å]. The water molecule engages in hydrogen bonding with the latter nitrogen atom; it is also connected to a symmetry-related water molecule to generate a linear chain structure.

Related literature top

For the crystal structure of 4-benzyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine, see: Ouzidan et al. (2010).

Experimental top

To a solution of the 6-bromo-2-(4-methoxyphenyl)-1H-imidazo[4,5-b]pyridine (0.33 g, 1.21 mmol), potassium carbonate (0.20 g, 1.42 mmol) and tetra-n-butylammonium bromide (0.04 g (0,1 mmol) in DMF (15 ml) was added benzyl chloride (0.15 ml, 1.31 mmol). Stirring was continued at room temperature for 12 hours. The salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was chromatographed on a column of silica gel with ethyl acetate/hexane (1/1) as eluent. Yellow crystals were isolated when the solvent was allowed to evaporate.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 C₂₀H₁₆BrN₃O^.H₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-Benzyl-6-bromo-2-(4-methoxyphenyl)-4H-imidazo[4,5-b]pyridine monohydrate top

Crystal data top

C₂₀H₁₆BrN₃O·H₂O	F(000) = 840
M_r = 412.28	D_x = 1.518 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6654 reflections
a = 10.5924 (2) Å	θ = 3.0–28.2°
b = 5.4544 (1) Å	µ = 2.30 mm⁻¹
c = 31.7444 (7) Å	T = 293 K
β = 100.292 (1)°	Prism, yellow
V = 1804.53 (6) Å³	0.29 × 0.13 × 0.09 mm
Z = 4

Data collection top

Bruker X8 APEXII diffractometer	5183 independent reflections
Radiation source: fine-focus sealed tube	3751 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 29.8°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.556, T_max = 0.820	k = −7→7
25327 measured reflections	l = −40→44

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0469P)² + 0.4879P] where P = (F_o² + 2F_c²)/3
5183 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.32 e Å⁻³
2 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₀H₁₆BrN₃O·H₂O	V = 1804.53 (6) Å³
M_r = 412.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5924 (2) Å	µ = 2.30 mm⁻¹
b = 5.4544 (1) Å	T = 293 K
c = 31.7444 (7) Å	0.29 × 0.13 × 0.09 mm
β = 100.292 (1)°

Data collection top

Bruker X8 APEXII diffractometer	5183 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3751 reflections with I > 2σ(I)
T_min = 0.556, T_max = 0.820	R_int = 0.029
25327 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.32 e Å⁻³
5183 reflections	Δρ_min = −0.38 e Å⁻³
244 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.33516 (2)	0.25313 (4)	0.229786 (7)	0.06505 (10)
O1W	0.0347 (2)	1.0524 (4)	0.27301 (7)	0.0809 (5)
H11	0.091 (3)	1.063 (10)	0.2955 (9)	0.18 (2)*
H12	0.032 (5)	1.199 (4)	0.2641 (17)	0.16 (2)*
N1	0.49030 (13)	0.4485 (3)	0.35254 (4)	0.0370 (3)
N2	0.25772 (13)	0.9195 (3)	0.34637 (4)	0.0397 (3)
N3	0.43173 (14)	0.7798 (2)	0.39573 (5)	0.0368 (3)
O1	0.24437 (17)	1.6309 (3)	0.50907 (5)	0.0663 (4)
C1	0.36408 (17)	0.4170 (3)	0.28302 (5)	0.0437 (4)
C2	0.28596 (17)	0.6138 (4)	0.28937 (5)	0.0438 (4)
H2	0.2193	0.6666	0.2682	0.053*
C3	0.31304 (16)	0.7260 (3)	0.32892 (6)	0.0380 (4)
C4	0.41915 (15)	0.6437 (3)	0.36032 (5)	0.0351 (3)
C5	0.46265 (17)	0.3344 (3)	0.31392 (6)	0.0417 (4)
H5	0.5108	0.1995	0.3084	0.050*
C6	0.33092 (15)	0.9407 (3)	0.38565 (5)	0.0355 (3)
C7	0.30567 (16)	1.1232 (3)	0.41692 (5)	0.0374 (3)
C8	0.20011 (19)	1.2782 (3)	0.40877 (6)	0.0466 (4)
H8	0.1446	1.2678	0.3826	0.056*
C9	0.17580 (19)	1.4476 (4)	0.43868 (6)	0.0501 (5)
H9	0.1041	1.5485	0.4327	0.060*
C10	0.25837 (19)	1.4669 (3)	0.47759 (6)	0.0462 (4)
C11	0.3644 (2)	1.3137 (4)	0.48642 (6)	0.0501 (5)
H11A	0.4197	1.3246	0.5126	0.060*
C12	0.38781 (18)	1.1462 (4)	0.45650 (5)	0.0448 (4)
H12A	0.4597	1.0458	0.4626	0.054*
C13	0.1389 (3)	1.7962 (4)	0.50100 (10)	0.0722 (7)
H13A	0.1424	1.9056	0.5249	0.108*
H13B	0.0601	1.7054	0.4971	0.108*
H13C	0.1431	1.8891	0.4756	0.108*
C14	0.60115 (17)	0.3669 (3)	0.38527 (6)	0.0409 (4)
H14A	0.6095	0.1901	0.3839	0.049*
H14B	0.5856	0.4091	0.4136	0.049*
C15	0.72405 (16)	0.4858 (3)	0.37807 (5)	0.0376 (4)
C16	0.76570 (19)	0.7021 (3)	0.39913 (6)	0.0460 (4)
H16	0.7194	0.7703	0.4185	0.055*
C17	0.8757 (2)	0.8163 (4)	0.39140 (8)	0.0592 (5)
H17	0.9033	0.9607	0.4057	0.071*
C18	0.9443 (2)	0.7187 (5)	0.36287 (8)	0.0675 (7)
H18	1.0174	0.7983	0.3574	0.081*
C19	0.9054 (2)	0.5027 (5)	0.34216 (7)	0.0644 (7)
H19	0.9529	0.4356	0.3230	0.077*
C20	0.79559 (18)	0.3847 (4)	0.34969 (6)	0.0495 (5)
H20	0.7698	0.2382	0.3358	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.06531 (16)	0.07264 (17)	0.05167 (13)	0.00232 (11)	−0.00455 (10)	−0.02553 (10)
O1W	0.0702 (12)	0.0877 (14)	0.0805 (13)	−0.0048 (10)	0.0017 (10)	0.0014 (11)
N1	0.0327 (7)	0.0387 (7)	0.0383 (7)	−0.0010 (6)	0.0027 (5)	0.0004 (6)
N2	0.0325 (7)	0.0490 (8)	0.0361 (7)	0.0033 (6)	0.0020 (5)	0.0001 (6)
N3	0.0330 (7)	0.0413 (8)	0.0349 (7)	0.0013 (6)	0.0024 (5)	0.0003 (5)
O1	0.0887 (11)	0.0604 (9)	0.0474 (8)	0.0241 (9)	0.0063 (7)	−0.0108 (7)
C1	0.0387 (9)	0.0493 (10)	0.0411 (8)	−0.0084 (8)	0.0018 (7)	−0.0091 (7)
C2	0.0340 (9)	0.0543 (11)	0.0402 (8)	−0.0023 (8)	−0.0016 (7)	−0.0028 (8)
C3	0.0296 (8)	0.0457 (10)	0.0375 (8)	−0.0033 (7)	0.0025 (6)	0.0006 (7)
C4	0.0292 (8)	0.0397 (8)	0.0357 (8)	−0.0028 (7)	0.0041 (6)	0.0022 (6)
C5	0.0388 (9)	0.0396 (9)	0.0460 (9)	−0.0031 (7)	0.0061 (7)	−0.0059 (7)
C6	0.0307 (8)	0.0414 (9)	0.0340 (7)	−0.0010 (7)	0.0044 (6)	0.0027 (6)
C7	0.0354 (8)	0.0419 (9)	0.0343 (8)	0.0007 (7)	0.0049 (6)	0.0026 (7)
C8	0.0423 (10)	0.0532 (11)	0.0407 (9)	0.0102 (8)	−0.0019 (7)	−0.0005 (7)
C9	0.0486 (11)	0.0530 (11)	0.0469 (10)	0.0175 (9)	0.0036 (8)	0.0006 (8)
C10	0.0568 (11)	0.0437 (10)	0.0382 (8)	0.0056 (8)	0.0090 (8)	0.0002 (7)
C11	0.0555 (11)	0.0559 (11)	0.0347 (9)	0.0090 (9)	−0.0035 (8)	−0.0017 (8)
C12	0.0424 (10)	0.0513 (10)	0.0380 (8)	0.0099 (8)	0.0000 (7)	0.0035 (8)
C13	0.0841 (18)	0.0593 (14)	0.0763 (17)	0.0176 (12)	0.0229 (14)	−0.0141 (12)
C14	0.0414 (9)	0.0387 (9)	0.0406 (8)	0.0037 (7)	0.0015 (7)	0.0072 (7)
C15	0.0337 (8)	0.0409 (9)	0.0359 (8)	0.0094 (7)	−0.0001 (6)	0.0084 (6)
C16	0.0436 (10)	0.0443 (10)	0.0477 (10)	0.0036 (8)	0.0020 (8)	0.0036 (7)
C17	0.0487 (12)	0.0578 (12)	0.0652 (13)	−0.0073 (10)	−0.0060 (10)	0.0126 (10)
C18	0.0383 (11)	0.097 (2)	0.0640 (14)	−0.0018 (11)	−0.0006 (10)	0.0325 (13)
C19	0.0426 (11)	0.107 (2)	0.0454 (10)	0.0293 (12)	0.0118 (9)	0.0190 (12)
C20	0.0471 (11)	0.0600 (12)	0.0386 (9)	0.0204 (9)	0.0006 (8)	0.0025 (8)

Geometric parameters (Å, º) top

Br1—C1	1.8877 (17)	C9—C10	1.384 (3)
O1w—H11	0.85 (1)	C9—H9	0.9300
O1w—H12	0.85 (1)	C10—C11	1.388 (3)
N1—C4	1.352 (2)	C11—C12	1.372 (3)
N1—C5	1.359 (2)	C11—H11A	0.9300
N1—C14	1.490 (2)	C12—H12A	0.9300
N2—C6	1.351 (2)	C13—H13A	0.9600
N2—C3	1.371 (2)	C13—H13B	0.9600
N3—C4	1.334 (2)	C13—H13C	0.9600
N3—C6	1.375 (2)	C14—C15	1.508 (2)
O1—C10	1.369 (2)	C14—H14A	0.9700
O1—C13	1.423 (3)	C14—H14B	0.9700
C1—C5	1.374 (3)	C15—C16	1.389 (3)
C1—C2	1.392 (3)	C15—C20	1.390 (3)
C2—C3	1.380 (2)	C16—C17	1.381 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.435 (2)	C17—C18	1.366 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.464 (2)	C18—C19	1.376 (4)
C7—C8	1.389 (2)	C18—H18	0.9300
C7—C12	1.400 (2)	C19—C20	1.387 (3)
C8—C9	1.382 (3)	C19—H19	0.9300
C8—H8	0.9300	C20—H20	0.9300

H11—O1W—H12	101 (5)	C12—C11—C10	120.05 (17)
C4—N1—C5	119.19 (14)	C12—C11—H11A	120.0
C4—N1—C14	120.23 (14)	C10—C11—H11A	120.0
C5—N1—C14	120.53 (15)	C11—C12—C7	121.39 (17)
C6—N2—C3	102.87 (13)	C11—C12—H12A	119.3
C4—N3—C6	101.69 (13)	C7—C12—H12A	119.3
C10—O1—C13	117.82 (18)	O1—C13—H13A	109.5
C5—C1—C2	123.00 (16)	O1—C13—H13B	109.5
C5—C1—Br1	117.70 (14)	H13A—C13—H13B	109.5
C2—C1—Br1	119.29 (13)	O1—C13—H13C	109.5
C3—C2—C1	116.21 (16)	H13A—C13—H13C	109.5
C3—C2—H2	121.9	H13B—C13—H13C	109.5
C1—C2—H2	121.9	N1—C14—C15	111.09 (13)
N2—C3—C2	132.43 (16)	N1—C14—H14A	109.4
N2—C3—C4	107.37 (14)	C15—C14—H14A	109.4
C2—C3—C4	120.19 (16)	N1—C14—H14B	109.4
N3—C4—N1	128.09 (14)	C15—C14—H14B	109.4
N3—C4—C3	111.05 (15)	H14A—C14—H14B	108.0
N1—C4—C3	120.84 (15)	C16—C15—C20	119.06 (18)
N1—C5—C1	120.50 (17)	C16—C15—C14	120.06 (16)
N1—C5—H5	119.8	C20—C15—C14	120.86 (17)
C1—C5—H5	119.8	C17—C16—C15	120.2 (2)
N2—C6—N3	116.99 (15)	C17—C16—H16	119.9
N2—C6—C7	122.69 (15)	C15—C16—H16	119.9
N3—C6—C7	120.31 (14)	C18—C17—C16	120.5 (2)
C8—C7—C12	117.59 (16)	C18—C17—H17	119.8
C8—C7—C6	121.75 (15)	C16—C17—H17	119.8
C12—C7—C6	120.66 (15)	C17—C18—C19	120.1 (2)
C9—C8—C7	121.45 (17)	C17—C18—H18	120.0
C9—C8—H8	119.3	C19—C18—H18	120.0
C7—C8—H8	119.3	C18—C19—C20	120.3 (2)
C8—C9—C10	119.90 (17)	C18—C19—H19	119.9
C8—C9—H9	120.0	C20—C19—H19	119.9
C10—C9—H9	120.0	C19—C20—C15	119.9 (2)
O1—C10—C9	124.58 (17)	C19—C20—H20	120.0
O1—C10—C11	115.81 (17)	C15—C20—H20	120.0
C9—C10—C11	119.61 (17)

C5—C1—C2—C3	0.4 (3)	N2—C6—C7—C12	−176.91 (17)
Br1—C1—C2—C3	−179.58 (13)	N3—C6—C7—C12	3.7 (2)
C6—N2—C3—C2	−178.68 (19)	C12—C7—C8—C9	−0.7 (3)
C6—N2—C3—C4	−0.05 (18)	C6—C7—C8—C9	179.03 (18)
C1—C2—C3—N2	−179.63 (18)	C7—C8—C9—C10	0.7 (3)
C1—C2—C3—C4	1.9 (3)	C13—O1—C10—C9	−1.2 (3)
C6—N3—C4—N1	−177.47 (17)	C13—O1—C10—C11	178.4 (2)
C6—N3—C4—C3	1.19 (18)	C8—C9—C10—O1	178.8 (2)
C5—N1—C4—N3	−179.48 (17)	C8—C9—C10—C11	−0.7 (3)
C14—N1—C4—N3	−2.2 (3)	O1—C10—C11—C12	−178.8 (2)
C5—N1—C4—C3	2.0 (2)	C9—C10—C11—C12	0.7 (3)
C14—N1—C4—C3	179.30 (15)	C10—C11—C12—C7	−0.8 (3)
N2—C3—C4—N3	−0.77 (19)	C8—C7—C12—C11	0.7 (3)
C2—C3—C4—N3	178.06 (16)	C6—C7—C12—C11	−178.99 (18)
N2—C3—C4—N1	178.00 (15)	C4—N1—C14—C15	−92.30 (18)
C2—C3—C4—N1	−3.2 (3)	C5—N1—C14—C15	84.99 (19)
C4—N1—C5—C1	0.3 (3)	N1—C14—C15—C16	93.17 (18)
C14—N1—C5—C1	−176.98 (16)	N1—C14—C15—C20	−85.35 (19)
C2—C1—C5—N1	−1.6 (3)	C20—C15—C16—C17	0.9 (3)
Br1—C1—C5—N1	178.39 (13)	C14—C15—C16—C17	−177.60 (17)
C3—N2—C6—N3	0.88 (19)	C15—C16—C17—C18	0.3 (3)
C3—N2—C6—C7	−178.50 (15)	C16—C17—C18—C19	−1.2 (3)
C4—N3—C6—N2	−1.33 (19)	C17—C18—C19—C20	0.8 (3)
C4—N3—C6—C7	178.06 (15)	C18—C19—C20—C15	0.4 (3)
N2—C6—C7—C8	3.4 (3)	C16—C15—C20—C19	−1.3 (2)
N3—C6—C7—C8	−175.95 (17)	C14—C15—C20—C19	177.23 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···N2	0.85 (1)	2.30 (2)	3.092 (3)	155 (5)
O1w—H12···O1Wⁱ	0.85 (1)	2.30 (2)	3.119 (2)	162 (5)

Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆BrN₃O·H₂O
M_r	412.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.5924 (2), 5.4544 (1), 31.7444 (7)
β (°)	100.292 (1)
V (Å³)	1804.53 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.29 × 0.13 × 0.09

Data collection
Diffractometer	Bruker X8 APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.556, 0.820
No. of measured, independent and observed [I > 2σ(I)] reflections	25327, 5183, 3751
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.700

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.098, 1.02
No. of reflections	5183
No. of parameters	244
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)	0.32, −0.38

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), 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—H11···N2	0.85 (1)	2.30 (2)	3.092 (3)	155 (5)
O1w—H12···O1Wⁱ	0.85 (1)	2.30 (2)	3.119 (2)	162 (5)

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

We thank Université Sidi Mohammed Ben Abdallah, 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
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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
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar